organic papers
Acta Cryst.(2007). E63, o1795–o1797 doi:10.1107/S1600536807011555 Yathirajanet al. C
17H20ClN2S+C6H2N3O7
o1795
Acta Crystallographica Section EStructure Reports
Online
ISSN 1600-5368
Chlorpromazinium picrate
H. S. Yathirajan,aM. A. Ashok,a B. Narayana Acharaand Michael Bolteb*
aDepartment of Studies in Chemistry, University
of Mysore, Manasagangotri, Mysore 570 006, India, andb
Institut fu¨r Anorganische Chemie, J. W. Goethe-Universita¨t Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study
T= 173 K
Mean(C–C) = 0.012 A˚
Rfactor = 0.095
wRfactor = 0.283
Data-to-parameter ratio = 13.0
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 1 March 2007 Accepted 12 March 2007
#2007 International Union of Crystallography
All rights reserved
The title compound [systematic name: N-(2-chloro-10H -phenothiazin-10-yl)-N,N-dimethylpropanaminium 2,4,6-tri-nitrophenolate], C17H20ClN2S
+.
C6H2N3O7
, belongs to a group of phenothiazine derivatives which exhibit pharmaco-logic activities. There are two anion–cation pairs in the asymmetric unit. The molecular conformations of the cations differ in the dihedral angles between the two outer aromatic rings of the phenothiazine unit and in two torsion angles of the side chain. The crystal packing is stabilized by N—H O and C—H O hydrogen bonds.
Comment
Chlorpromazine, chemically 2-chloro-N,N-dimethyl-10H -phenothiazine-10-propanamine, was the first antipsychotic drug, used during the 1950s and 1960s, and is an aliphatic phenothiazine. The aliphatic phenothiazines are highly sedating, which is often apparent at the start of therapy; with time some tolerance to this effect develops. Chlorpromazine has strong -adrenergic blocking activity and can cause orthostatic hypotension. Chlorpromazine has moderate anti-cholinergic activity, manifested as occasional dry mouth, blurred vision, urinary retention and constipation. Chlorpro-mazine increases prolactin secretion owing to its dopamine receptor blocking action in the pituitary and hypothalamus. Chlorpromazine is considered a typical antipsychotic and acts as an antagonist (blocking agent) on different postsynaptic receptors. Chlorpromazine has a wide range of activity arising from its depressant actions on the central nervous system and its -adrenergic blocking and weak antimuscarinic activities. Cationic phenothiazine derivatives also act as -electron donors and can form charge-transfer (CT) complexes with organic compounds. The donor activity of phenothiazines is so high that, even in the ground state, there is practically total transfer of an electron to an acceptor with the formation of CT complexes (Karpinska et al., 1996). The properties and analytical application of chlorpromazine picrate have been reported (Tarasiewicz & Basinska, 1974). A review of various aspects of phenothiazines has been published (Kojilo et al., 2001).
different angles between the two aromatic rings of the phenothiazine unit, the cations differ in two torsion angles of the side chain (Table 1).
The crystal packing is stabilized by N—H O hydrogen bonds and several weak C—H O contacts (Table 2). It it interesting to note that one cation–anion pair is connected by
whereas there is a bifurcated N—H O hydrogen bond in the second pair. In addition, the distance between the amino H atom and the phenol O atom is significantly shorter in the first pair than in the second one.
Experimental
Chlorpromazine hydrochloride (1.0670 g, 0.03 M) and picric acid (0.6885 g, 0.03M) were dissolved separately in doubly distilled water (100 ml). Both solutions were mixed and stirred in a beaker. The phenothiazine derivative formed a salt with picric acid instanta-neously at room temperature. The separated orange salt was filtered off, washed thoroughly with doubly distilled water and dried in a vacuum desiccator over phosphorus pentoxide. The compound was recrystallized from acetonitrile (m.p. 434 K).
Crystal data
C17H20ClN2S+C6H2N3O7
Mr= 547.97
Triclinic,P1
a= 12.3355 (14) A˚
b= 14.6631 (19) A˚
c= 15.5340 (19) A˚
= 100.922 (9) V= 2458.6 (6) A˚3
Z= 4
MoKradiation
= 0.30 mm1
[image:2.610.47.296.69.266.2]T= 173 (2) K
Figure 1
[image:2.610.347.548.72.269.2]The structure of one ion-pair of the asymmetric unit of the title compound, with the atom numbering. Displacement ellipsoids are drawn at the 50% probability level. The dashed line indicates a hydrogen bond.
Figure 2
The structure of the other ion-pair of the asymmetric unit of the title compound, with the atom numbering. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds.
Figure 3
[image:2.610.51.291.318.611.2]Data collection Stoe IPDS-II two-circle
diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)
Tmin= 0.948,Tmax= 0.998
30547 measured reflections 8664 independent reflections 4240 reflections withI> 2(I)
Rint= 0.089
Refinement
R[F2> 2(F2)] = 0.095
wR(F2) = 0.283
S= 0.98 8664 reflections
667 parameters
H-atom parameters constrained
max= 0.94 e A˚
3
min=0.54 e A˚
3
Table 1
Selected torsion angles ().
C22—N1—C1—C2 81.1 (7) C1—C2—C3—N4 170.6 (5)
[image:3.610.315.565.71.113.2] [image:3.610.44.294.345.453.2]C22A—N1A—C1A—C2A 77.6 (7) C1A—C2A—C3A—N4A 147.8 (5)
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
N4—H4 O31 0.93 1.73 2.605 (9) 156 N4A—H4A O31A 0.93 1.91 2.723 (7) 145 N4A—H4A O32A 0.93 2.28 2.940 (7) 127 C1A—H1A1 O36B 0.99 2.45 3.261 (9) 139 C2—H2B O31 0.99 2.56 3.229 (10) 125 C3—H3A Cl1Ai
0.99 2.70 3.457 (6) 133 C3—H3B O342ii 0.99 2.56 3.477 (8) 154 C4—H4D O36Biii
0.98 2.45 3.426 (13) 172 C5—H5C O341ii
0.98 2.57 3.354 (10) 137 C3A—H3A2 O34Bii
0.99 2.41 3.312 (10) 152
D—H A D—H H A D A D—H A
C5A—H5A1 O34Biv
0.98 2.48 3.453 (11) 172 C5A—H5A2 O32A 0.98 2.51 3.047 (10) 114 C15A—H15A O342v
0.95 2.53 3.315 (11) 140
Symmetry codes: (i)x1;y;z1; (ii) x1;y;z; (iii)xþ1;yþ1;zþ1; (iv)
xþ2;y;zþ2; (v)x;y;zþ1.
H atoms were found in a difference map, but they were refined using a riding model with C—H ranging from 0.95 to 0.99 A˚ and N— H = 0.93 A˚ , and withUiso(H) = 1.2Ueq(C,N) or 1.5Ueq(Cmethyl).
Data collection: X-AREA (Stoe & Cie, 2001); cell refinement:
X-AREA; data reduction: X-AREA; program(s) used to solve structure:SHELXS97(Sheldrick, 1997); program(s) used to refine structure:SHELXL97(Sheldrick, 1997); molecular graphics:XPin
SHELXTL-Plus(Sheldrick, 1991); software used to prepare material for publication:SHELXL97.
HSY and MAA thank the University of Mysore for research facilities.
References
Allen, F. H. (2002).Acta Cryst.B58, 380–388. Blessing, R. H. (1995).Acta Cryst.A51, 33–38.
Bruno, I. J., Cole, J. C., Kessler, M., Luo, J., Motherwell, W. D. S., Purkis, L. H., Smith, B. R., Taylor, R., Cooper, R. I., Harris, S. E. & Orpen, A. G. (2004).J. Chem. Inf. Comput. Sci.44, 2133–2144.
Karpinska, J., Starczewska, B. & Puzanowska-Tarasiewicz, H. (1996).Anal. Sci.12, 161–170.
Kojilo, A., Karpinska, J., Kuzmicka, L., Misiuk, W., Puzanowska-Tarasiewicz, H. & Tarasiewicz, M. (2001).J. Trace Microprobe Tech.19, 45–70. Sheldrick, G. M. (1991).SHELXTL-Plus. Release 4.1. Siemens Analytical
X-ray Instruments Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.
Spek, A. L. (2003).J. Appl. Cryst.36, 7–13.
Stoe & Cie (2001).X-AREA. Stoe & Cie, Darmstadt, Germany. Tarasiewicz, M. & Basinska, H. (1974).Talanta,21, 425–430.
organic papers
Acta Cryst.(2007). E63, o1795–o1797 Yathirajanet al. C
supporting information
Acta Cryst. (2007). E63, o1795–o1797 [https://doi.org/10.1107/S1600536807011555]
Chlorpromazinium picrate
H. S. Yathirajan, M. A. Ashok, B. Narayana Achar and Michael Bolte
N-(2-chloro-10H-phenothiazin-10-yl)-N,N-dimethylpropanaminium 2,4,6-trinitrophenolate
Crystal data
C17H20ClN2S+·C6H2N3O7−
Mr = 547.97
Triclinic, P1
Hall symbol: -P 1
a = 12.3355 (14) Å
b = 14.6631 (19) Å
c = 15.5340 (19) Å
α = 108.758 (10)°
β = 104.675 (10)°
γ = 100.922 (9)°
V = 2458.6 (6) Å3
Z = 4
F(000) = 1136
Dx = 1.480 Mg m−3
Mo Kα radiation, λ = 0.71073 Å
Cell parameters from 12532 reflections
θ = 3.6–25.6°
µ = 0.30 mm−1
T = 173 K
Plate, orange
0.22 × 0.18 × 0.04 mm
Data collection
Stoe IPDS-II two-circle diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω scans
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
Tmin = 0.948, Tmax = 0.998
30547 measured reflections 8664 independent reflections 4240 reflections with I > 2σ(I)
Rint = 0.089
θmax = 25.0°, θmin = 3.5°
h = −14→14
k = −17→15
l = −18→18
Refinement
Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.095
wR(F2) = 0.283
S = 0.98
8664 reflections 667 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained w = 1/[σ2(F
o2) + (0.1443P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.94 e Å−3
Δρmin = −0.54 e Å−3
Special details
supporting information
sup-2 Acta Cryst. (2007). E63, o1795–o1797
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2,
conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used
only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2
are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
S1 −0.1012 (2) 0.19166 (16) 0.39451 (16) 0.0923 (8)
Cl1 0.3626 (3) 0.3746 (3) 0.3353 (2) 0.1123 (9)
N1 −0.0614 (5) 0.3582 (4) 0.3216 (4) 0.0572 (15)
C1 −0.0689 (6) 0.4121 (4) 0.2554 (4) 0.0511 (16)
H1A −0.1528 0.4030 0.2234 0.061*
H1B −0.0380 0.3793 0.2045 0.061*
C2 −0.0036 (5) 0.5260 (4) 0.3009 (4) 0.0455 (15)
H2A −0.0277 0.5607 0.3558 0.055*
H2B 0.0822 0.5377 0.3246 0.055*
C3 −0.0369 (5) 0.5651 (4) 0.2217 (4) 0.0419 (14)
H3A −0.0263 0.5208 0.1631 0.050*
H3B −0.1210 0.5614 0.2056 0.050*
N4 0.0336 (4) 0.6712 (4) 0.2486 (4) 0.0482 (13)
H4 0.1122 0.6735 0.2628 0.058*
C4 −0.0009 (9) 0.6998 (7) 0.1629 (7) 0.103 (3)
H4B −0.0845 0.6950 0.1446 0.154*
H4C 0.0141 0.6540 0.1085 0.154*
H4D 0.0453 0.7692 0.1797 0.154*
C5 0.0211 (6) 0.7455 (5) 0.3345 (6) 0.073 (2)
H5A 0.0694 0.8132 0.3483 0.110*
H5B 0.0469 0.7278 0.3905 0.110*
H5C −0.0613 0.7444 0.3212 0.110*
C11 0.0340 (8) 0.2527 (5) 0.3889 (5) 0.072 (2)
C12 0.0366 (7) 0.3255 (5) 0.3458 (5) 0.0591 (19)
C13 0.1400 (8) 0.3605 (6) 0.3286 (5) 0.068 (2)
H13 0.1445 0.4077 0.2988 0.082*
C14 0.2357 (8) 0.3261 (6) 0.3554 (6) 0.079 (2)
C15 0.2352 (10) 0.2577 (7) 0.3989 (6) 0.084 (3)
H15 0.3021 0.2359 0.4171 0.101*
C16 0.1326 (10) 0.2218 (6) 0.4152 (5) 0.086 (3)
H16 0.1299 0.1746 0.4451 0.103*
C21 −0.1606 (7) 0.2939 (6) 0.4177 (5) 0.072 (2)
C22 −0.1389 (6) 0.3652 (6) 0.3774 (5) 0.064 (2)
C23 −0.1957 (6) 0.4393 (6) 0.3910 (5) 0.064 (2)
H23 −0.1806 0.4884 0.3645 0.077*
C24 −0.2766 (7) 0.4446 (7) 0.4438 (5) 0.086 (3)
H24 −0.3146 0.4958 0.4525 0.103*
C25 −0.2966 (8) 0.3711 (8) 0.4817 (6) 0.091 (3)
H25 −0.3500 0.3714 0.5163 0.109*
H26 −0.2530 0.2486 0.4963 0.096*
O31 0.2287 (5) 0.6237 (6) 0.2635 (6) 0.110 (2)
C31 0.3274 (6) 0.6110 (7) 0.2617 (6) 0.067 (2)
C32 0.4359 (6) 0.6851 (5) 0.3330 (5) 0.0575 (18)
C33 0.5456 (5) 0.6735 (5) 0.3382 (5) 0.0466 (15)
H33 0.6142 0.7214 0.3881 0.056*
C34 0.5527 (5) 0.5906 (5) 0.2689 (4) 0.0470 (15)
C35 0.4520 (5) 0.5197 (5) 0.1962 (5) 0.0530 (16)
H35 0.4585 0.4640 0.1475 0.064*
C36 0.3458 (6) 0.5302 (6) 0.1950 (6) 0.0591 (18)
N32 0.4344 (8) 0.7775 (6) 0.4058 (7) 0.081 (2)
O321 0.3562 (8) 0.8150 (6) 0.3797 (5) 0.122 (3)
O322 0.5063 (6) 0.8117 (4) 0.4877 (5) 0.0809 (16)
N34 0.6659 (5) 0.5772 (5) 0.2693 (4) 0.0607 (15)
O341 0.7538 (4) 0.6420 (4) 0.3338 (4) 0.0752 (15)
O342 0.6709 (4) 0.5026 (5) 0.2073 (4) 0.0796 (16)
N36 0.2439 (5) 0.4508 (6) 0.1133 (6) 0.075 (2)
O361 0.2563 (5) 0.4188 (5) 0.0338 (5) 0.096 (2)
O362 0.1535 (5) 0.4258 (6) 0.1303 (5) 0.112 (2)
S1A 0.2816 (2) 0.15171 (16) 0.80216 (15) 0.0746 (6)
Cl1A 0.8219 (3) 0.3829 (2) 0.99075 (19) 0.1497 (16)
N1A 0.4753 (5) 0.0837 (4) 0.7412 (4) 0.0544 (14)
C1A 0.5576 (5) 0.0242 (6) 0.7241 (5) 0.0572 (18)
H1A1 0.6354 0.0606 0.7750 0.069*
H1A2 0.5671 0.0172 0.6611 0.069*
C2A 0.5148 (5) −0.0793 (5) 0.7242 (4) 0.0491 (15)
H2A1 0.5708 −0.1178 0.7112 0.059*
H2A2 0.4376 −0.1166 0.6729 0.059*
C3A 0.5041 (6) −0.0685 (5) 0.8225 (5) 0.0504 (16)
H3A1 0.5595 −0.0036 0.8720 0.061*
H3A2 0.4237 −0.0666 0.8206 0.061*
N4A 0.5289 (4) −0.1528 (3) 0.8516 (3) 0.0394 (11)
H4A 0.6041 −0.1541 0.8517 0.047*
C4A 0.4470 (6) −0.2524 (5) 0.7838 (5) 0.068 (2)
H4A1 0.4673 −0.3045 0.8058 0.102*
H4A2 0.4525 −0.2661 0.7193 0.102*
H4A3 0.3667 −0.2529 0.7813 0.102*
C5A 0.5275 (6) −0.1340 (6) 0.9524 (5) 0.0596 (18)
H5A1 0.5825 −0.0678 0.9970 0.089*
H5A2 0.5509 −0.1865 0.9721 0.089*
H5A3 0.4482 −0.1354 0.9538 0.089*
C11A 0.4349 (9) 0.2207 (6) 0.8508 (5) 0.078 (3)
C12A 0.5150 (7) 0.1763 (5) 0.8156 (5) 0.0600 (19)
C13A 0.6356 (8) 0.2315 (6) 0.8608 (5) 0.080 (3)
H13A 0.6924 0.2059 0.8377 0.096*
C14A 0.6697 (11) 0.3209 (8) 0.9372 (7) 0.102 (4)
C15A 0.5924 (15) 0.3660 (7) 0.9730 (7) 0.118 (5)
supporting information
sup-4 Acta Cryst. (2007). E63, o1795–o1797
C16A 0.4720 (13) 0.3153 (7) 0.9287 (6) 0.105 (4)
H16A 0.4164 0.3441 0.9507 0.126*
C21A 0.2766 (6) 0.0935 (5) 0.6828 (5) 0.0492 (16)
C22A 0.3717 (5) 0.0620 (4) 0.6631 (4) 0.0433 (14)
C23A 0.3583 (5) 0.0095 (5) 0.5670 (5) 0.0490 (15)
H23A 0.4200 −0.0148 0.5518 0.059*
C24A 0.2563 (5) −0.0079 (5) 0.4928 (5) 0.0490 (15)
H24A 0.2489 −0.0441 0.4277 0.059*
C25A 0.1659 (6) 0.0267 (5) 0.5130 (5) 0.0551 (17)
H25A 0.0972 0.0160 0.4619 0.066*
C26A 0.1750 (6) 0.0763 (5) 0.6063 (6) 0.0560 (17)
H26A 0.1120 0.0996 0.6200 0.067*
O31A 0.7529 (3) −0.0780 (3) 0.8606 (3) 0.0524 (11)
C31A 0.8520 (5) −0.0902 (4) 0.8712 (4) 0.0371 (13)
C32A 0.8977 (4) −0.1485 (4) 0.9232 (4) 0.0362 (13)
C33A 1.0085 (5) −0.1598 (4) 0.9398 (4) 0.0429 (14)
H33A 1.0346 −0.1953 0.9785 0.052*
C34A 1.0815 (5) −0.1175 (5) 0.8980 (4) 0.0423 (14)
C35A 1.0460 (5) −0.0607 (4) 0.8467 (4) 0.0393 (13)
H35A 1.0968 −0.0315 0.8196 0.047*
C36A 0.9386 (5) −0.0470 (4) 0.8351 (4) 0.0411 (14)
N32A 0.8237 (4) −0.1941 (4) 0.9672 (4) 0.0468 (12)
O32A 0.7180 (4) −0.2336 (4) 0.9226 (4) 0.0687 (15)
O32B 0.8725 (4) −0.1919 (4) 1.0480 (3) 0.0583 (12)
N34A 1.1965 (4) −0.1294 (4) 0.9124 (4) 0.0579 (15)
O34A 1.2262 (4) −0.1821 (5) 0.9567 (4) 0.0818 (17)
O34B 1.2625 (4) −0.0864 (5) 0.8803 (5) 0.0852 (18)
N36A 0.9109 (5) 0.0187 (4) 0.7832 (4) 0.0570 (15)
O36A 0.9633 (4) 0.0281 (4) 0.7266 (3) 0.0692 (14)
O36B 0.8409 (4) 0.0651 (4) 0.8018 (5) 0.0856 (19)
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
S1 0.142 (2) 0.0451 (11) 0.0775 (13) −0.0040 (12) 0.0257 (13) 0.0354 (10)
Cl1 0.114 (2) 0.142 (3) 0.138 (2) 0.0787 (19) 0.0674 (17) 0.084 (2)
N1 0.073 (4) 0.035 (3) 0.057 (3) −0.003 (3) 0.013 (3) 0.028 (3)
C1 0.057 (4) 0.034 (3) 0.056 (4) −0.002 (3) 0.010 (3) 0.025 (3)
C2 0.047 (3) 0.033 (3) 0.053 (3) 0.000 (3) 0.010 (3) 0.024 (3)
C3 0.041 (3) 0.029 (3) 0.054 (3) 0.010 (2) 0.008 (3) 0.019 (3)
N4 0.034 (3) 0.040 (3) 0.078 (3) 0.014 (2) 0.013 (2) 0.034 (3)
C4 0.126 (8) 0.055 (5) 0.117 (7) 0.006 (5) 0.000 (6) 0.065 (5)
C5 0.052 (4) 0.035 (4) 0.112 (6) 0.007 (3) 0.025 (4) 0.008 (4)
C11 0.119 (7) 0.038 (4) 0.050 (4) 0.019 (4) 0.018 (4) 0.018 (3)
C12 0.088 (5) 0.034 (4) 0.049 (4) 0.014 (3) 0.011 (3) 0.019 (3)
C13 0.100 (6) 0.049 (4) 0.069 (5) 0.032 (4) 0.034 (4) 0.031 (4)
C14 0.112 (7) 0.059 (5) 0.073 (5) 0.045 (5) 0.022 (5) 0.030 (4)
C16 0.145 (9) 0.061 (5) 0.061 (5) 0.053 (6) 0.021 (5) 0.033 (4)
C21 0.088 (5) 0.057 (5) 0.051 (4) −0.008 (4) 0.007 (4) 0.023 (3)
C22 0.067 (4) 0.052 (4) 0.056 (4) −0.018 (4) 0.006 (3) 0.030 (3)
C23 0.061 (4) 0.056 (5) 0.062 (4) −0.008 (4) 0.012 (3) 0.027 (4)
C24 0.080 (5) 0.087 (6) 0.058 (4) −0.021 (5) 0.003 (4) 0.029 (4)
C25 0.078 (6) 0.101 (8) 0.067 (5) −0.021 (6) 0.015 (4) 0.034 (5)
C26 0.086 (6) 0.074 (6) 0.062 (5) −0.019 (5) 0.016 (4) 0.037 (4)
O31 0.063 (4) 0.164 (7) 0.188 (7) 0.072 (4) 0.078 (4) 0.126 (6)
C31 0.042 (4) 0.090 (6) 0.111 (6) 0.030 (4) 0.036 (4) 0.077 (5)
C32 0.070 (5) 0.057 (4) 0.088 (5) 0.041 (4) 0.050 (4) 0.050 (4)
C33 0.047 (4) 0.039 (4) 0.067 (4) 0.014 (3) 0.028 (3) 0.029 (3)
C34 0.040 (3) 0.053 (4) 0.059 (4) 0.017 (3) 0.021 (3) 0.030 (3)
C35 0.050 (4) 0.051 (4) 0.070 (4) 0.021 (3) 0.018 (3) 0.037 (3)
C36 0.045 (4) 0.060 (5) 0.092 (5) 0.019 (3) 0.028 (4) 0.047 (4)
N32 0.111 (6) 0.081 (5) 0.123 (6) 0.059 (5) 0.086 (5) 0.077 (5)
O321 0.199 (8) 0.137 (6) 0.150 (6) 0.140 (6) 0.120 (6) 0.105 (5)
O322 0.105 (5) 0.060 (4) 0.099 (4) 0.026 (3) 0.062 (4) 0.037 (3)
N34 0.041 (3) 0.088 (5) 0.067 (4) 0.034 (3) 0.023 (3) 0.035 (4)
O341 0.040 (3) 0.090 (4) 0.093 (4) 0.021 (3) 0.024 (3) 0.030 (3)
O342 0.058 (3) 0.106 (5) 0.075 (3) 0.047 (3) 0.027 (3) 0.019 (3)
N36 0.041 (4) 0.083 (5) 0.113 (6) 0.011 (3) 0.014 (4) 0.065 (5)
O361 0.074 (4) 0.075 (4) 0.110 (5) 0.002 (3) 0.001 (4) 0.034 (4)
O362 0.042 (3) 0.144 (6) 0.161 (6) 0.003 (3) 0.015 (3) 0.101 (5)
S1A 0.1149 (17) 0.0662 (13) 0.0803 (13) 0.0475 (12) 0.0584 (12) 0.0441 (11)
Cl1A 0.185 (3) 0.0876 (19) 0.0857 (16) −0.0586 (19) −0.0375 (17) 0.0395 (14)
N1A 0.049 (3) 0.046 (3) 0.066 (3) 0.009 (3) 0.009 (3) 0.030 (3)
C1A 0.036 (3) 0.073 (5) 0.080 (4) 0.018 (3) 0.021 (3) 0.050 (4)
C2A 0.042 (3) 0.063 (4) 0.054 (4) 0.024 (3) 0.016 (3) 0.032 (3)
C3A 0.048 (4) 0.059 (4) 0.066 (4) 0.028 (3) 0.021 (3) 0.043 (3)
N4A 0.029 (2) 0.038 (3) 0.058 (3) 0.010 (2) 0.016 (2) 0.026 (2)
C4A 0.057 (4) 0.051 (4) 0.082 (5) 0.006 (3) 0.007 (4) 0.026 (4)
C5A 0.049 (4) 0.081 (5) 0.069 (4) 0.028 (4) 0.024 (3) 0.046 (4)
C11A 0.134 (8) 0.044 (4) 0.050 (4) 0.011 (5) 0.019 (4) 0.029 (4)
C12A 0.083 (5) 0.048 (4) 0.052 (4) 0.014 (4) 0.014 (4) 0.033 (4)
C13A 0.095 (6) 0.056 (5) 0.055 (4) −0.019 (4) −0.014 (4) 0.032 (4)
C14A 0.151 (9) 0.057 (6) 0.058 (5) −0.019 (6) −0.008 (6) 0.034 (5)
C15A 0.238 (16) 0.036 (5) 0.054 (5) 0.008 (7) 0.039 (8) 0.012 (4)
C16A 0.203 (12) 0.059 (6) 0.063 (5) 0.029 (7) 0.052 (7) 0.037 (5)
C21A 0.065 (4) 0.039 (3) 0.065 (4) 0.022 (3) 0.033 (3) 0.034 (3)
C22A 0.034 (3) 0.043 (3) 0.065 (4) 0.013 (3) 0.017 (3) 0.034 (3)
C23A 0.036 (3) 0.050 (4) 0.067 (4) 0.014 (3) 0.021 (3) 0.026 (3)
C24A 0.050 (4) 0.049 (4) 0.055 (4) 0.015 (3) 0.020 (3) 0.028 (3)
C25A 0.045 (4) 0.052 (4) 0.074 (5) 0.018 (3) 0.014 (3) 0.036 (4)
C26A 0.050 (4) 0.048 (4) 0.093 (5) 0.030 (3) 0.031 (4) 0.040 (4)
O31A 0.029 (2) 0.060 (3) 0.087 (3) 0.0167 (19) 0.017 (2) 0.052 (2)
C31A 0.029 (3) 0.035 (3) 0.047 (3) 0.009 (2) 0.005 (2) 0.022 (3)
C32A 0.027 (3) 0.036 (3) 0.056 (3) 0.015 (2) 0.016 (2) 0.025 (3)
supporting information
sup-6 Acta Cryst. (2007). E63, o1795–o1797
C34A 0.028 (3) 0.043 (3) 0.059 (4) 0.009 (2) 0.013 (3) 0.026 (3)
C35A 0.028 (3) 0.037 (3) 0.055 (3) 0.005 (2) 0.016 (2) 0.023 (3)
C36A 0.032 (3) 0.034 (3) 0.058 (3) 0.005 (2) 0.009 (3) 0.025 (3)
N32A 0.039 (3) 0.049 (3) 0.068 (3) 0.020 (2) 0.018 (2) 0.037 (3)
O32A 0.035 (2) 0.083 (4) 0.122 (4) 0.020 (2) 0.028 (3) 0.079 (3)
O32B 0.062 (3) 0.061 (3) 0.070 (3) 0.017 (2) 0.027 (2) 0.044 (2)
N34A 0.038 (3) 0.058 (4) 0.089 (4) 0.019 (3) 0.025 (3) 0.037 (3)
O34A 0.048 (3) 0.100 (4) 0.140 (5) 0.040 (3) 0.037 (3) 0.086 (4)
O34B 0.041 (3) 0.107 (5) 0.152 (5) 0.032 (3) 0.051 (3) 0.086 (4)
N36A 0.032 (3) 0.056 (4) 0.079 (4) 0.002 (3) 0.002 (3) 0.040 (3)
O36A 0.075 (3) 0.076 (4) 0.065 (3) 0.007 (3) 0.023 (3) 0.046 (3)
O36B 0.049 (3) 0.093 (4) 0.167 (6) 0.035 (3) 0.044 (3) 0.103 (4)
Geometric parameters (Å, º)
S1—C21 1.766 (10) S1A—C21A 1.753 (7)
S1—C11 1.775 (9) S1A—C11A 1.796 (10)
Cl1—C14 1.739 (10) Cl1A—C14A 1.766 (11)
N1—C12 1.391 (9) N1A—C12A 1.369 (9)
N1—C22 1.441 (10) N1A—C22A 1.421 (7)
N1—C1 1.481 (7) N1A—C1A 1.477 (9)
C1—C2 1.543 (8) C1A—C2A 1.511 (9)
C1—H1A 0.9900 C1A—H1A1 0.9900
C1—H1B 0.9900 C1A—H1A2 0.9900
C2—C3 1.515 (8) C2A—C3A 1.526 (8)
C2—H2A 0.9900 C2A—H2A1 0.9900
C2—H2B 0.9900 C2A—H2A2 0.9900
C3—N4 1.496 (7) C3A—N4A 1.503 (7)
C3—H3A 0.9900 C3A—H3A1 0.9900
C3—H3B 0.9900 C3A—H3A2 0.9900
N4—C5 1.492 (9) N4A—C4A 1.476 (8)
N4—C4 1.507 (9) N4A—C5A 1.506 (8)
N4—H4 0.9300 N4A—H4A 0.9300
C4—H4B 0.9800 C4A—H4A1 0.9800
C4—H4C 0.9800 C4A—H4A2 0.9800
C4—H4D 0.9800 C4A—H4A3 0.9800
C5—H5A 0.9800 C5A—H5A1 0.9800
C5—H5B 0.9800 C5A—H5A2 0.9800
C5—H5C 0.9800 C5A—H5A3 0.9800
C11—C16 1.388 (12) C11A—C12A 1.410 (12)
C11—C12 1.430 (9) C11A—C16A 1.414 (12)
C12—C13 1.405 (11) C12A—C13A 1.418 (11)
C13—C14 1.390 (11) C13A—C14A 1.357 (13)
C13—H13 0.9500 C13A—H13A 0.9500
C14—C15 1.378 (11) C14A—C15A 1.388 (17)
C15—C16 1.392 (13) C15A—C16A 1.403 (17)
C15—H15 0.9500 C15A—H15A 0.9500
C21—C22 1.398 (9) C21A—C22A 1.406 (9)
C21—C26 1.401 (12) C21A—C26A 1.407 (9)
C22—C23 1.391 (11) C22A—C23A 1.392 (9)
C23—C24 1.441 (11) C23A—C24A 1.389 (8)
C23—H23 0.9500 C23A—H23A 0.9500
C24—C25 1.397 (12) C24A—C25A 1.373 (9)
C24—H24 0.9500 C24A—H24A 0.9500
C25—C26 1.390 (14) C25A—C26A 1.361 (10)
C25—H25 0.9500 C25A—H25A 0.9500
C26—H26 0.9500 C26A—H26A 0.9500
O31—C31 1.272 (8) O31A—C31A 1.245 (6)
C31—C36 1.400 (11) C31A—C32A 1.449 (7)
C31—C32 1.457 (11) C31A—C36A 1.460 (8)
C32—C33 1.381 (9) C32A—C33A 1.377 (8)
C32—N32 1.467 (10) C32A—N32A 1.458 (7)
C33—C34 1.375 (9) C33A—C34A 1.401 (8)
C33—H33 0.9500 C33A—H33A 0.9500
C34—C35 1.394 (9) C34A—C35A 1.381 (8)
C34—N34 1.446 (8) C34A—N34A 1.432 (8)
C35—C36 1.345 (9) C35A—C36A 1.354 (8)
C35—H35 0.9500 C35A—H35A 0.9500
C36—N36 1.493 (10) C36A—N36A 1.477 (8)
N32—O322 1.226 (9) N32A—O32A 1.229 (6)
N32—O321 1.243 (9) N32A—O32B 1.234 (6)
N34—O342 1.227 (8) N34A—O34B 1.234 (7)
N34—O341 1.236 (7) N34A—O34A 1.235 (7)
N36—O362 1.227 (8) N36A—O36B 1.231 (8)
N36—O361 1.232 (9) N36A—O36A 1.242 (7)
C21—S1—C11 99.0 (4) C21A—S1A—C11A 96.5 (4)
C12—N1—C22 121.3 (5) C12A—N1A—C22A 118.5 (6)
C12—N1—C1 119.0 (6) C12A—N1A—C1A 119.6 (6)
C22—N1—C1 117.7 (6) C22A—N1A—C1A 118.1 (6)
N1—C1—C2 116.7 (5) N1A—C1A—C2A 111.7 (5)
N1—C1—H1A 108.1 N1A—C1A—H1A1 109.3
C2—C1—H1A 108.1 C2A—C1A—H1A1 109.3
N1—C1—H1B 108.1 N1A—C1A—H1A2 109.3
C2—C1—H1B 108.1 C2A—C1A—H1A2 109.3
H1A—C1—H1B 107.3 H1A1—C1A—H1A2 107.9
C3—C2—C1 106.3 (5) C1A—C2A—C3A 109.2 (6)
C3—C2—H2A 110.5 C1A—C2A—H2A1 109.8
C1—C2—H2A 110.5 C3A—C2A—H2A1 109.8
C3—C2—H2B 110.5 C1A—C2A—H2A2 109.8
C1—C2—H2B 110.5 C3A—C2A—H2A2 109.8
H2A—C2—H2B 108.7 H2A1—C2A—H2A2 108.3
N4—C3—C2 113.4 (4) N4A—C3A—C2A 112.9 (5)
N4—C3—H3A 108.9 N4A—C3A—H3A1 109.0
supporting information
sup-8 Acta Cryst. (2007). E63, o1795–o1797
N4—C3—H3B 108.9 N4A—C3A—H3A2 109.0
C2—C3—H3B 108.9 C2A—C3A—H3A2 109.0
H3A—C3—H3B 107.7 H3A1—C3A—H3A2 107.8
C5—N4—C3 113.6 (5) C4A—N4A—C3A 112.8 (5)
C5—N4—C4 110.2 (6) C4A—N4A—C5A 110.0 (5)
C3—N4—C4 108.9 (5) C3A—N4A—C5A 110.8 (5)
C5—N4—H4 108.0 C4A—N4A—H4A 107.7
C3—N4—H4 108.0 C3A—N4A—H4A 107.7
C4—N4—H4 108.0 C5A—N4A—H4A 107.7
N4—C4—H4B 109.5 N4A—C4A—H4A1 109.5
N4—C4—H4C 109.5 N4A—C4A—H4A2 109.5
H4B—C4—H4C 109.5 H4A1—C4A—H4A2 109.5
N4—C4—H4D 109.5 N4A—C4A—H4A3 109.5
H4B—C4—H4D 109.5 H4A1—C4A—H4A3 109.5
H4C—C4—H4D 109.5 H4A2—C4A—H4A3 109.5
N4—C5—H5A 109.5 N4A—C5A—H5A1 109.5
N4—C5—H5B 109.5 N4A—C5A—H5A2 109.5
H5A—C5—H5B 109.5 H5A1—C5A—H5A2 109.5
N4—C5—H5C 109.5 N4A—C5A—H5A3 109.5
H5A—C5—H5C 109.5 H5A1—C5A—H5A3 109.5
H5B—C5—H5C 109.5 H5A2—C5A—H5A3 109.5
C16—C11—C12 120.1 (8) C12A—C11A—C16A 122.0 (9)
C16—C11—S1 120.4 (6) C12A—C11A—S1A 119.6 (6)
C12—C11—S1 119.0 (6) C16A—C11A—S1A 118.2 (9)
N1—C12—C13 122.5 (6) N1A—C12A—C11A 120.1 (7)
N1—C12—C11 120.1 (7) N1A—C12A—C13A 122.8 (8)
C13—C12—C11 117.4 (7) C11A—C12A—C13A 117.1 (8)
C14—C13—C12 120.0 (7) C14A—C13A—C12A 119.9 (10)
C14—C13—H13 120.0 C14A—C13A—H13A 120.0
C12—C13—H13 120.0 C12A—C13A—H13A 120.0
C15—C14—C13 123.1 (9) C13A—C14A—C15A 123.9 (10)
C15—C14—Cl1 118.9 (7) C13A—C14A—Cl1A 116.8 (11)
C13—C14—Cl1 118.0 (6) C15A—C14A—Cl1A 119.3 (9)
C14—C15—C16 117.2 (8) C14A—C15A—C16A 118.1 (9)
C14—C15—H15 121.4 C14A—C15A—H15A 121.0
C16—C15—H15 121.4 C16A—C15A—H15A 121.0
C11—C16—C15 122.1 (8) C15A—C16A—C11A 118.9 (11)
C11—C16—H16 119.0 C15A—C16A—H16A 120.6
C15—C16—H16 119.0 C11A—C16A—H16A 120.6
C22—C21—C26 120.2 (9) C22A—C21A—C26A 120.0 (6)
C22—C21—S1 120.5 (7) C22A—C21A—S1A 120.7 (5)
C26—C21—S1 119.0 (6) C26A—C21A—S1A 119.3 (5)
C23—C22—C21 118.2 (8) C23A—C22A—C21A 117.6 (5)
C23—C22—N1 122.3 (6) C23A—C22A—N1A 123.2 (6)
C21—C22—N1 119.4 (8) C21A—C22A—N1A 119.2 (6)
C22—C23—C24 122.6 (7) C24A—C23A—C22A 121.2 (6)
C22—C23—H23 118.7 C24A—C23A—H23A 119.4
C25—C24—C23 117.0 (10) C25A—C24A—C23A 120.4 (6)
C25—C24—H24 121.5 C25A—C24A—H24A 119.8
C23—C24—H24 121.5 C23A—C24A—H24A 119.8
C26—C25—C24 120.6 (9) C26A—C25A—C24A 119.9 (6)
C26—C25—H25 119.7 C26A—C25A—H25A 120.0
C24—C25—H25 119.7 C24A—C25A—H25A 120.0
C25—C26—C21 121.3 (8) C25A—C26A—C21A 120.7 (6)
C25—C26—H26 119.4 C25A—C26A—H26A 119.6
C21—C26—H26 119.4 C21A—C26A—H26A 119.6
O31—C31—C36 126.3 (8) O31A—C31A—C32A 124.1 (5)
O31—C31—C32 120.4 (8) O31A—C31A—C36A 125.4 (5)
C36—C31—C32 113.3 (6) C32A—C31A—C36A 110.6 (5)
C33—C32—C31 123.4 (7) C33A—C32A—C31A 125.5 (5)
C33—C32—N32 115.6 (7) C33A—C32A—N32A 116.7 (5)
C31—C32—N32 121.1 (7) C31A—C32A—N32A 117.7 (5)
C34—C33—C32 118.0 (6) C32A—C33A—C34A 118.1 (5)
C34—C33—H33 121.0 C32A—C33A—H33A 120.9
C32—C33—H33 121.0 C34A—C33A—H33A 120.9
C33—C34—C35 121.0 (6) C35A—C34A—C33A 120.8 (5)
C33—C34—N34 120.0 (6) C35A—C34A—N34A 119.6 (5)
C35—C34—N34 118.9 (6) C33A—C34A—N34A 119.5 (5)
C36—C35—C34 119.9 (7) C36A—C35A—C34A 119.8 (5)
C36—C35—H35 120.1 C36A—C35A—H35A 120.1
C34—C35—H35 120.1 C34A—C35A—H35A 120.1
C35—C36—C31 124.3 (7) C35A—C36A—C31A 125.1 (5)
C35—C36—N36 115.6 (7) C35A—C36A—N36A 115.7 (5)
C31—C36—N36 120.1 (7) C31A—C36A—N36A 119.2 (5)
O322—N32—O321 124.1 (8) O32A—N32A—O32B 123.5 (5)
O322—N32—C32 119.7 (7) O32A—N32A—C32A 119.5 (5)
O321—N32—C32 116.2 (9) O32B—N32A—C32A 117.0 (5)
O342—N34—O341 123.1 (6) O34B—N34A—O34A 122.4 (5)
O342—N34—C34 119.3 (6) O34B—N34A—C34A 118.7 (5)
O341—N34—C34 117.6 (6) O34A—N34A—C34A 118.9 (5)
O362—N36—O361 125.5 (8) O36B—N36A—O36A 123.3 (6)
O362—N36—C36 117.1 (8) O36B—N36A—C36A 118.0 (6)
O361—N36—C36 117.4 (6) O36A—N36A—C36A 118.6 (6)
C12—N1—C1—C2 −82.8 (8) C12A—N1A—C1A—C2A 124.5 (6)
C22—N1—C1—C2 81.1 (7) C22A—N1A—C1A—C2A −77.6 (7)
N1—C1—C2—C3 −173.3 (6) N1A—C1A—C2A—C3A −60.7 (7)
C1—C2—C3—N4 −170.6 (5) C1A—C2A—C3A—N4A −147.8 (5)
C2—C3—N4—C5 −60.5 (7) C2A—C3A—N4A—C4A −61.1 (7)
C2—C3—N4—C4 176.3 (7) C2A—C3A—N4A—C5A 175.1 (5)
C21—S1—C11—C16 150.5 (6) C21A—S1A—C11A—C12A −36.5 (6)
C21—S1—C11—C12 −37.2 (6) C21A—S1A—C11A—C16A 148.0 (6)
C22—N1—C12—C13 −148.5 (6) C22A—N1A—C12A—C11A 40.8 (8)
C1—N1—C12—C13 14.8 (9) C1A—N1A—C12A—C11A −161.4 (6)
supporting information
sup-10 Acta Cryst. (2007). E63, o1795–o1797
C1—N1—C12—C11 −164.4 (6) C1A—N1A—C12A—C13A 18.2 (9)
C16—C11—C12—N1 −178.6 (7) C16A—C11A—C12A—N1A 178.8 (6)
S1—C11—C12—N1 9.1 (9) S1A—C11A—C12A—N1A 3.5 (8)
C16—C11—C12—C13 2.2 (10) C16A—C11A—C12A—C13A −0.9 (10)
S1—C11—C12—C13 −170.1 (5) S1A—C11A—C12A—C13A −176.1 (5)
N1—C12—C13—C14 179.3 (7) N1A—C12A—C13A—C14A −176.9 (6)
C11—C12—C13—C14 −1.5 (10) C11A—C12A—C13A—C14A 2.7 (9)
C12—C13—C14—C15 0.1 (12) C12A—C13A—C14A—C15A −2.9 (12)
C12—C13—C14—Cl1 −178.3 (6) C12A—C13A—C14A—Cl1A 178.5 (5)
C13—C14—C15—C16 0.7 (13) C13A—C14A—C15A—C16A 1.2 (13)
Cl1—C14—C15—C16 179.0 (6) Cl1A—C14A—C15A—C16A 179.7 (6)
C12—C11—C16—C15 −1.5 (12) C14A—C15A—C16A—C11A 0.7 (12)
S1—C11—C16—C15 170.7 (6) C12A—C11A—C16A—C15A −0.8 (11)
C14—C15—C16—C11 0.1 (13) S1A—C11A—C16A—C15A 174.5 (6)
C11—S1—C21—C22 34.6 (6) C11A—S1A—C21A—C22A 36.4 (5)
C11—S1—C21—C26 −151.6 (6) C11A—S1A—C21A—C26A −145.1 (5)
C26—C21—C22—C23 0.8 (10) C26A—C21A—C22A—C23A −3.3 (8)
S1—C21—C22—C23 174.6 (5) S1A—C21A—C22A—C23A 175.3 (4)
C26—C21—C22—N1 −177.7 (6) C26A—C21A—C22A—N1A 177.4 (5)
S1—C21—C22—N1 −3.9 (9) S1A—C21A—C22A—N1A −4.0 (7)
C12—N1—C22—C23 146.1 (6) C12A—N1A—C22A—C23A 139.7 (6)
C1—N1—C22—C23 −17.4 (9) C1A—N1A—C22A—C23A −18.4 (8)
C12—N1—C22—C21 −35.4 (9) C12A—N1A—C22A—C21A −41.1 (8)
C1—N1—C22—C21 161.0 (6) C1A—N1A—C22A—C21A 160.8 (5)
C21—C22—C23—C24 −0.7 (10) C21A—C22A—C23A—C24A 2.3 (9)
N1—C22—C23—C24 177.7 (6) N1A—C22A—C23A—C24A −178.5 (5)
C22—C23—C24—C25 0.0 (10) C22A—C23A—C24A—C25A 0.1 (9)
C23—C24—C25—C26 0.8 (11) C23A—C24A—C25A—C26A −1.6 (9)
C24—C25—C26—C21 −0.8 (12) C24A—C25A—C26A—C21A 0.5 (10)
C22—C21—C26—C25 −0.1 (11) C22A—C21A—C26A—C25A 2.0 (9)
S1—C21—C26—C25 −173.9 (6) S1A—C21A—C26A—C25A −176.6 (5)
O31—C31—C32—C33 176.7 (6) O31A—C31A—C32A—C33A −177.0 (6)
C36—C31—C32—C33 −4.0 (9) C36A—C31A—C32A—C33A 2.0 (8)
O31—C31—C32—N32 −2.3 (10) O31A—C31A—C32A—N32A −1.2 (9)
C36—C31—C32—N32 177.0 (6) C36A—C31A—C32A—N32A 177.8 (5)
C31—C32—C33—C34 4.0 (9) C31A—C32A—C33A—C34A −4.6 (9)
N32—C32—C33—C34 −177.0 (5) N32A—C32A—C33A—C34A 179.6 (5)
C32—C33—C34—C35 −0.7 (9) C32A—C33A—C34A—C35A 4.0 (9)
C32—C33—C34—N34 177.8 (5) C32A—C33A—C34A—N34A −178.9 (6)
C33—C34—C35—C36 −2.2 (9) C33A—C34A—C35A—C36A −1.1 (9)
N34—C34—C35—C36 179.3 (6) N34A—C34A—C35A—C36A −178.2 (6)
C34—C35—C36—C31 2.0 (10) C34A—C35A—C36A—C31A −1.6 (9)
C34—C35—C36—N36 179.2 (6) C34A—C35A—C36A—N36A 177.3 (6)
O31—C31—C36—C35 −179.8 (6) O31A—C31A—C36A—C35A −179.8 (6)
C32—C31—C36—C35 1.0 (9) C32A—C31A—C36A—C35A 1.2 (8)
O31—C31—C36—N36 3.1 (11) O31A—C31A—C36A—N36A 1.4 (9)
C32—C31—C36—N36 −176.2 (6) C32A—C31A—C36A—N36A −177.7 (5)
C31—C32—N32—O322 143.6 (7) C31A—C32A—N32A—O32A 41.4 (8)
C33—C32—N32—O321 146.2 (7) C33A—C32A—N32A—O32B 36.4 (8)
C31—C32—N32—O321 −34.7 (9) C31A—C32A—N32A—O32B −139.8 (5)
C33—C34—N34—O342 179.7 (6) C35A—C34A—N34A—O34B 1.7 (9)
C35—C34—N34—O342 −1.7 (9) C33A—C34A—N34A—O34B −175.4 (6)
C33—C34—N34—O341 0.4 (9) C35A—C34A—N34A—O34A −178.6 (6)
C35—C34—N34—O341 178.9 (6) C33A—C34A—N34A—O34A 4.3 (9)
C35—C36—N36—O362 145.0 (7) C35A—C36A—N36A—O36B −152.2 (6)
C31—C36—N36—O362 −37.6 (9) C31A—C36A—N36A—O36B 26.8 (8)
C35—C36—N36—O361 −37.7 (9) C35A—C36A—N36A—O36A 24.4 (8)
C31—C36—N36—O361 139.7 (7) C31A—C36A—N36A—O36A −156.7 (5)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
N4—H4···O31 0.93 1.73 2.605 (9) 156
N4A—H4A···O31A 0.93 1.91 2.723 (7) 145
N4A—H4A···O32A 0.93 2.28 2.940 (7) 127
C1A—H1A1···O36B 0.99 2.45 3.261 (9) 139
C2—H2B···O31 0.99 2.56 3.229 (10) 125
C3—H3A···Cl1Ai 0.99 2.70 3.457 (6) 133
C3—H3B···O342ii 0.99 2.56 3.477 (8) 154
C4—H4D···O36Biii 0.98 2.45 3.426 (13) 172
C5—H5C···O341ii 0.98 2.57 3.354 (10) 137
C3A—H3A2···O34Bii 0.99 2.41 3.312 (10) 152
C5A—H5A1···O34Biv 0.98 2.48 3.453 (11) 172
C5A—H5A2···O32A 0.98 2.51 3.047 (10) 114
C15A—H15A···O342v 0.95 2.53 3.315 (11) 140
