organic papers
Acta Cryst.(2007). E63, o1691–o1692 doi:10.1107/S1600536807009877 Yathirajanet al. C
19H23N2S+C6H2N3O7
o1691
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
Mepazinium 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) = 0.002 A˚
Rfactor = 0.036
wRfactor = 0.097
Data-to-parameter ratio = 13.4
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 23 February 2007 Accepted 1 March 2007
#2007 International Union of Crystallography All rights reserved
The title compound [systematic name: 1-methyl-3-(10H
-phenothiazin-10-ylmethyl)piperidinium
2,4,6-trinitrophenol-ate], C19H23N2S +.
C6H2N3O7
, is a pharmacologically active compound. The dihedral angle between the two outer
aromatic rings of the phenothiazine unit is 41.58 (7). The
crystal packing is stabilized by N—H O hydrogen bonds and
several weak C—H O contacts.
Comment
Mepazine, chemically 10-[(1-methyl-3-piperidyl)methyl]-10H -phenothiazine, is an antipsychotic drug (Tedeschiet al., 1958). In continuation of our work on the crystallization of phenothiazine drugs with picrate (Yathirajanet al., 2007), we present here the formation of a salt by the interaction between
10-[(1-methyl-3-piperidyl)methyl]-10H-phenothiazine
hydro-chloride and 2,4,6-trinitrophenol in an aqueous medium.
[image:1.610.240.423.373.482.2] [image:1.610.209.458.569.717.2]A perspective view of the structure of (I) is shown in Fig. 1. Bond lengths and angles can be regarded as normal (Cambridge Structural Database, Version 5.28, November 2006; Allen, 2002;Mogul, Version 1.1; Brunoet al., 2004). The
Figure 1
dihedral angle between the two aromatic rings of the phenothiazine unit is 41.58 (7). The piperidyl ring adopts a
chair conformation with both substituents in equatorial posi-tions. The crystal packing is stabilized by N—H O hydrogen
bonds and several weak C—H O contacts (Table 1).
Experimental
Mepazine hydrochloride monohydrate (0.7300 g, 0.02M) and picric acid (0.4606 g, 0.02M) were dissolved separately in doubly distilled water (100 ml). The solutions were mixed and stirred in a beaker. A bright-yellow salt was formed instantaneously at room temperature. The separated salt was filtered off, washed thoroughly with doubly distilled water and dried in a vacuum desiccator over phosphorus pentoxide. The compound was recrystallized from ethanol (m.p. 379 K).
Crystal data C19H23N2S+C6H2N3O7
Mr= 539.56
Triclinic,P1
a= 8.3584 (9) A˚
b= 10.7782 (9) A˚
c= 14.5062 (13) A˚
= 93.524 (7) = 99.629 (8)
= 102.419 (7) V= 1251.8 (2) A˚3
Z= 2
MoKradiation
= 0.19 mm1
T= 173 (2) K 0.450.450.40 mm
Data collection Stoe IPDSII two-circle
diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)
Tmin= 0.911,Tmax= 0.920
12751 measured reflections 4656 independent reflections 3824 reflections withI> 2(I)
Rint= 0.037
Refinement
R[F2> 2(F2)] = 0.037
wR(F2) = 0.098
S= 1.03 4656 reflections 348 parameters
H atoms treated by a mixture of independent and constrained refinement
max= 0.24 e A˚ 3
[image:2.610.313.563.95.176.2]min=0.31 e A˚ 3
Table 1
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
N4—H4 O31 0.89 (2) 1.84 (2) 2.6879 (17) 158.2 (19) N4—H4 O321 0.89 (2) 2.46 (2) 3.0191 (17) 121.8 (16) C3—H3B O321 0.99 2.50 3.0790 (19) 117 C5—H5B O342i
0.99 2.50 3.409 (2) 152 C6—H6A O362 0.99 2.47 3.419 (2) 160 C6—H6B O341ii
0.99 2.56 3.4229 (19) 146 C35—H35 O322iii
0.95 2.52 3.4568 (19) 168
Symmetry codes: (i)x1;y1;z; (ii)x;y1;z; (iii)xþ1;y;z.
H atoms were found in a difference map. The H atom bonded to nitrogen was refined freely and all other H atoms were refined using a riding model, with C—H = 0.95–0.99 A˚ andUiso(H) = 1.2Ueq(C) or
1.5Ueq(methyl C).
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:SHELXL97andPLATON(Spek, 2003).
MAA thanks the University of Mysore for research facil-ities.
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 Jie 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.
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.
Tedeschi, D. H., Benigni, J. P., Elder, C. J., Yeager, J. C. & Flanigan, J. V. (1958).
J. Pharmacol. Exp. Ther.123, 35–38.
supporting information
sup-1 Acta Cryst. (2007). E63, o1691–o1692
supporting information
Acta Cryst. (2007). E63, o1691–o1692 [https://doi.org/10.1107/S1600536807009877]
Mepazinium picrate
H. S. Yathirajan, M. A. Ashok, B. Narayana Achar and Michael Bolte
1-methyl-3-(10H-phenothiazin-10-ylmethyl)piperidinium 2,4,6-trinitrophenolate
Crystal data
C19H23N2S+·C6H2N3O7−
Mr = 539.56 Triclinic, P1 Hall symbol: -P 1
a = 8.3584 (9) Å
b = 10.7782 (9) Å
c = 14.5062 (13) Å
α = 93.524 (7)°
β = 99.629 (8)°
γ = 102.419 (7)°
V = 1251.8 (2) Å3
Z = 2
F(000) = 564
Dx = 1.431 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 11665 reflections
θ = 3.6–25.7°
µ = 0.19 mm−1
T = 173 K Block, yellow
0.45 × 0.45 × 0.40 mm
Data collection
Stoe IPDSII two-circle diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω scans
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
Tmin = 0.911, Tmax = 0.920
12751 measured reflections 4656 independent reflections 3824 reflections with I > 2σ(I)
Rint = 0.037
θmax = 25.6°, θmin = 3.5°
h = −10→9
k = −13→13
l = −17→17
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.037
wR(F2) = 0.098
S = 1.03 4656 reflections 348 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 atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(F
o2) + (0.0554P)2 + 0.2289P]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.24 e Å−3
Δρmin = −0.31 e Å−3
Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full
covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
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 0.02175 (7) 0.37989 (5) 0.35523 (3) 0.04206 (15) N1 0.28825 (18) 0.24026 (12) 0.40629 (9) 0.0268 (3) C1 0.3945 (2) 0.14854 (15) 0.40418 (11) 0.0281 (4)
H1A 0.3353 0.0661 0.4218 0.034*
H1B 0.4974 0.1801 0.4519 0.034*
C2 0.4430 (2) 0.12556 (14) 0.30814 (11) 0.0237 (3)
H2 0.5123 0.2071 0.2933 0.028*
C3 0.28805 (19) 0.08374 (14) 0.23111 (11) 0.0224 (3)
H3A 0.2160 0.0047 0.2460 0.027*
H3B 0.2238 0.1510 0.2280 0.027*
N4 0.33760 (16) 0.05998 (12) 0.13795 (9) 0.0217 (3) H4 0.402 (3) 0.132 (2) 0.1256 (14) 0.041 (6)* C5 0.4332 (2) −0.04426 (14) 0.13991 (12) 0.0298 (4)
H5A 0.4653 −0.0579 0.0781 0.036*
H5B 0.3614 −0.1251 0.1522 0.036*
C6 0.5888 (2) −0.00758 (16) 0.21622 (13) 0.0329 (4)
H6A 0.6661 0.0675 0.1997 0.039*
H6B 0.6460 −0.0791 0.2195 0.039*
C7 0.5469 (2) 0.02409 (15) 0.31244 (13) 0.0312 (4)
H7A 0.6514 0.0558 0.3589 0.037*
H7B 0.4838 −0.0544 0.3335 0.037*
C8 0.1906 (2) 0.03098 (15) 0.06006 (12) 0.0298 (4)
H8A 0.1321 0.1006 0.0605 0.045*
H8B 0.1149 −0.0489 0.0685 0.045*
H8C 0.2277 0.0221 −0.0001 0.045*
C11 0.2373 (3) 0.44361 (16) 0.35978 (11) 0.0330 (4) C12 0.3513 (2) 0.36750 (14) 0.38561 (11) 0.0275 (4) C13 0.5205 (2) 0.41886 (15) 0.38934 (11) 0.0322 (4)
H13 0.5990 0.3696 0.4094 0.039*
C14 0.5765 (3) 0.54132 (16) 0.36413 (12) 0.0400 (5)
H14 0.6920 0.5744 0.3660 0.048*
C15 0.4627 (3) 0.61440 (17) 0.33643 (13) 0.0466 (5)
H15 0.5000 0.6973 0.3182 0.056*
C16 0.2945 (3) 0.56665 (17) 0.33535 (12) 0.0435 (5)
supporting information
sup-3 Acta Cryst. (2007). E63, o1691–o1692
C21 0.0389 (2) 0.28760 (16) 0.45189 (11) 0.0318 (4) C22 0.1689 (2) 0.22330 (15) 0.46664 (11) 0.0267 (4) C23 0.1764 (2) 0.14648 (15) 0.54057 (12) 0.0316 (4)
H23 0.2651 0.1040 0.5525 0.038*
C24 0.0554 (3) 0.13102 (17) 0.59742 (13) 0.0381 (4)
H24 0.0604 0.0762 0.6461 0.046*
C25 −0.0716 (3) 0.19527 (18) 0.58296 (13) 0.0411 (4)
H25 −0.1538 0.1848 0.6216 0.049*
C26 −0.0782 (2) 0.27549 (18) 0.51133 (13) 0.0405 (4)
H26 −0.1629 0.3223 0.5028 0.049*
O31 0.56325 (14) 0.23524 (10) 0.07476 (8) 0.0273 (3) C31 0.64495 (19) 0.34878 (13) 0.09897 (10) 0.0198 (3) C32 0.57653 (18) 0.45812 (14) 0.11859 (10) 0.0205 (3) C33 0.67187 (19) 0.58233 (13) 0.13681 (10) 0.0207 (3)
H33 0.6202 0.6514 0.1459 0.025*
C34 0.84247 (19) 0.60521 (13) 0.14171 (10) 0.0198 (3) C35 0.92134 (19) 0.50618 (13) 0.12421 (10) 0.0195 (3)
H35 1.0382 0.5225 0.1260 0.023*
C36 0.82353 (18) 0.38509 (13) 0.10438 (10) 0.0189 (3) N32 0.39911 (16) 0.44032 (12) 0.12034 (9) 0.0230 (3) N34 0.94252 (17) 0.73405 (11) 0.16701 (9) 0.0236 (3) N36 0.90516 (16) 0.28134 (11) 0.08304 (9) 0.0216 (3) O321 0.32327 (15) 0.33772 (11) 0.14170 (10) 0.0359 (3) O322 0.33216 (14) 0.52989 (11) 0.10250 (9) 0.0322 (3) O341 0.87183 (15) 0.82411 (10) 0.16471 (9) 0.0347 (3) O342 1.09587 (14) 0.74930 (10) 0.19020 (8) 0.0293 (3) O361 0.97890 (16) 0.28866 (11) 0.01673 (9) 0.0351 (3) O362 0.89583 (17) 0.19274 (11) 0.13283 (9) 0.0367 (3)
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C21 0.0363 (10) 0.0343 (9) 0.0235 (8) 0.0126 (7) −0.0012 (7) −0.0049 (7) C22 0.0329 (9) 0.0248 (7) 0.0204 (7) 0.0072 (7) 0.0009 (7) −0.0050 (6) C23 0.0390 (10) 0.0273 (8) 0.0286 (9) 0.0099 (7) 0.0040 (8) 0.0007 (7) C24 0.0522 (12) 0.0309 (9) 0.0291 (9) 0.0039 (8) 0.0099 (8) −0.0006 (7) C25 0.0457 (12) 0.0407 (10) 0.0367 (10) 0.0067 (9) 0.0148 (9) −0.0048 (8) C26 0.0374 (11) 0.0459 (10) 0.0388 (10) 0.0156 (9) 0.0055 (8) −0.0085 (8) O31 0.0253 (6) 0.0207 (5) 0.0337 (6) −0.0022 (4) 0.0111 (5) −0.0035 (4) C31 0.0213 (8) 0.0207 (7) 0.0176 (7) 0.0021 (6) 0.0073 (6) 0.0017 (5) C32 0.0159 (8) 0.0248 (7) 0.0217 (7) 0.0039 (6) 0.0067 (6) 0.0027 (6) C33 0.0220 (8) 0.0212 (7) 0.0217 (7) 0.0070 (6) 0.0089 (6) 0.0025 (6) C34 0.0212 (8) 0.0171 (7) 0.0209 (7) 0.0015 (6) 0.0075 (6) 0.0011 (5) C35 0.0180 (8) 0.0213 (7) 0.0200 (7) 0.0037 (6) 0.0066 (6) 0.0023 (6) C36 0.0207 (8) 0.0190 (7) 0.0187 (7) 0.0058 (6) 0.0072 (6) 0.0009 (5) N32 0.0182 (7) 0.0269 (7) 0.0246 (7) 0.0048 (5) 0.0066 (5) 0.0020 (5) N34 0.0259 (8) 0.0195 (6) 0.0257 (7) 0.0024 (5) 0.0101 (6) 0.0007 (5) N36 0.0208 (7) 0.0184 (6) 0.0256 (7) 0.0030 (5) 0.0076 (5) −0.0011 (5) O321 0.0234 (6) 0.0305 (6) 0.0553 (8) 0.0005 (5) 0.0164 (6) 0.0100 (5) O322 0.0243 (6) 0.0372 (6) 0.0402 (7) 0.0141 (5) 0.0095 (5) 0.0090 (5) O341 0.0363 (7) 0.0184 (5) 0.0532 (8) 0.0085 (5) 0.0173 (6) −0.0002 (5) O342 0.0230 (6) 0.0247 (6) 0.0357 (7) −0.0027 (5) 0.0039 (5) 0.0008 (5) O361 0.0434 (8) 0.0352 (6) 0.0359 (7) 0.0151 (6) 0.0255 (6) 0.0031 (5) O362 0.0478 (8) 0.0265 (6) 0.0459 (7) 0.0172 (5) 0.0225 (6) 0.0130 (5)
Geometric parameters (Å, º)
S1—C11 1.773 (2) C14—C15 1.385 (3)
S1—C21 1.7724 (18) C14—H14 0.9500
N1—C22 1.424 (2) C15—C16 1.386 (3)
N1—C12 1.429 (2) C15—H15 0.9500
N1—C1 1.466 (2) C16—H16 0.9500
C1—C2 1.535 (2) C21—C26 1.400 (3)
C1—H1A 0.9900 C21—C22 1.404 (2)
C1—H1B 0.9900 C22—C23 1.396 (2)
C2—C3 1.527 (2) C23—C24 1.398 (3)
C2—C7 1.534 (2) C23—H23 0.9500
C2—H2 1.0000 C24—C25 1.381 (3)
C3—N4 1.5012 (19) C24—H24 0.9500
C3—H3A 0.9900 C25—C26 1.394 (3)
C3—H3B 0.9900 C25—H25 0.9500
N4—C8 1.487 (2) C26—H26 0.9500
N4—C5 1.5112 (19) O31—C31 1.2628 (17)
N4—H4 0.89 (2) C31—C36 1.447 (2)
C5—C6 1.522 (3) C31—C32 1.449 (2)
C5—H5A 0.9900 C32—C33 1.387 (2)
C5—H5B 0.9900 C32—N32 1.4586 (19)
C6—C7 1.531 (2) C33—C34 1.383 (2)
C6—H6A 0.9900 C33—H33 0.9500
supporting information
sup-5 Acta Cryst. (2007). E63, o1691–o1692
C7—H7A 0.9900 C34—N34 1.4484 (18)
C7—H7B 0.9900 C35—C36 1.368 (2)
C8—H8A 0.9800 C35—H35 0.9500
C8—H8B 0.9800 C36—N36 1.4724 (18)
C8—H8C 0.9800 N32—O322 1.2356 (17)
C11—C16 1.398 (3) N32—O321 1.2358 (17)
C11—C12 1.406 (2) N34—O341 1.2395 (17)
C12—C13 1.394 (3) N34—O342 1.2416 (18)
C13—C14 1.395 (2) N36—O361 1.2240 (17)
C13—H13 0.9500 N36—O362 1.2294 (17)
C11—S1—C21 98.18 (8) C12—C13—C14 121.14 (17)
C22—N1—C12 117.14 (12) C12—C13—H13 119.4
C22—N1—C1 118.35 (13) C14—C13—H13 119.4
C12—N1—C1 118.43 (14) C15—C14—C13 119.6 (2)
N1—C1—C2 113.71 (12) C15—C14—H14 120.2
N1—C1—H1A 108.8 C13—C14—H14 120.2
C2—C1—H1A 108.8 C14—C15—C16 120.05 (17)
N1—C1—H1B 108.8 C14—C15—H15 120.0
C2—C1—H1B 108.8 C16—C15—H15 120.0
H1A—C1—H1B 107.7 C15—C16—C11 120.64 (18)
C3—C2—C7 110.48 (13) C15—C16—H16 119.7
C3—C2—C1 110.79 (13) C11—C16—H16 119.7
C7—C2—C1 109.42 (13) C26—C21—C22 120.16 (16)
C3—C2—H2 108.7 C26—C21—S1 120.68 (14)
C7—C2—H2 108.7 C22—C21—S1 119.13 (13)
C1—C2—H2 108.7 C23—C22—C21 118.42 (16)
N4—C3—C2 110.09 (12) C23—C22—N1 122.90 (15)
N4—C3—H3A 109.6 C21—C22—N1 118.68 (14)
C2—C3—H3A 109.6 C22—C23—C24 121.09 (17)
N4—C3—H3B 109.6 C22—C23—H23 119.5
C2—C3—H3B 109.6 C24—C23—H23 119.5
H3A—C3—H3B 108.2 C25—C24—C23 120.18 (17)
C8—N4—C3 111.41 (12) C25—C24—H24 119.9
C8—N4—C5 111.58 (12) C23—C24—H24 119.9
C3—N4—C5 110.92 (12) C24—C25—C26 119.58 (18)
C8—N4—H4 105.0 (14) C24—C25—H25 120.2
C3—N4—H4 108.5 (13) C26—C25—H25 120.2
C5—N4—H4 109.2 (13) C25—C26—C21 120.50 (18)
N4—C5—C6 110.20 (12) C25—C26—H26 119.8
N4—C5—H5A 109.6 C21—C26—H26 119.8
C6—C5—H5A 109.6 O31—C31—C36 121.86 (13)
N4—C5—H5B 109.6 O31—C31—C32 126.30 (14)
C6—C5—H5B 109.6 C36—C31—C32 111.73 (12)
H5A—C5—H5B 108.1 C33—C32—C31 123.34 (13)
C5—C6—C7 111.73 (14) C33—C32—N32 116.69 (13)
C5—C6—H6A 109.3 C31—C32—N32 119.97 (13)
C5—C6—H6B 109.3 C34—C33—H33 120.2
C7—C6—H6B 109.3 C32—C33—H33 120.2
H6A—C6—H6B 107.9 C33—C34—C35 121.50 (13)
C6—C7—C2 111.04 (14) C33—C34—N34 119.35 (13)
C6—C7—H7A 109.4 C35—C34—N34 119.14 (13)
C2—C7—H7A 109.4 C36—C35—C34 117.40 (14)
C6—C7—H7B 109.4 C36—C35—H35 121.3
C2—C7—H7B 109.4 C34—C35—H35 121.3
H7A—C7—H7B 108.0 C35—C36—C31 126.25 (13)
N4—C8—H8A 109.5 C35—C36—N36 117.55 (13)
N4—C8—H8B 109.5 C31—C36—N36 116.16 (12)
H8A—C8—H8B 109.5 O322—N32—O321 122.88 (13)
N4—C8—H8C 109.5 O322—N32—C32 118.38 (12)
H8A—C8—H8C 109.5 O321—N32—C32 118.72 (12)
H8B—C8—H8C 109.5 O341—N34—O342 122.86 (12)
C16—C11—C12 119.71 (19) O341—N34—C34 118.82 (13) C16—C11—S1 120.98 (15) O342—N34—C34 118.32 (12) C12—C11—S1 119.28 (13) O361—N36—O362 123.81 (12) C13—C12—C11 118.75 (15) O361—N36—C36 117.92 (12) C13—C12—N1 122.83 (15) O362—N36—C36 118.27 (12) C11—C12—N1 118.42 (16)
supporting information
sup-7 Acta Cryst. (2007). E63, o1691–o1692
C12—C13—C14—C15 1.1 (3) C33—C32—N32—O322 26.6 (2) C13—C14—C15—C16 1.1 (3) C31—C32—N32—O322 −153.68 (13) C14—C15—C16—C11 −1.6 (3) C33—C32—N32—O321 −151.69 (14) C12—C11—C16—C15 −0.1 (3) C31—C32—N32—O321 28.0 (2) S1—C11—C16—C15 −178.09 (14) C33—C34—N34—O341 −14.8 (2) C11—S1—C21—C26 143.82 (15) C35—C34—N34—O341 166.24 (13) C11—S1—C21—C22 −38.10 (15) C33—C34—N34—O342 165.15 (13) C26—C21—C22—C23 0.9 (2) C35—C34—N34—O342 −13.8 (2) S1—C21—C22—C23 −177.19 (12) C35—C36—N36—O361 −58.59 (18) C26—C21—C22—N1 −178.46 (15) C31—C36—N36—O361 119.31 (15) S1—C21—C22—N1 3.4 (2) C35—C36—N36—O362 121.21 (15) C12—N1—C22—C23 −134.91 (16) C31—C36—N36—O362 −60.90 (18)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
N4—H4···O31 0.89 (2) 1.84 (2) 2.6879 (17) 158.2 (19) N4—H4···O321 0.89 (2) 2.46 (2) 3.0191 (17) 121.8 (16)
C3—H3B···O321 0.99 2.50 3.0790 (19) 117
C5—H5B···O342i 0.99 2.50 3.409 (2) 152
C6—H6A···O362 0.99 2.47 3.419 (2) 160
C6—H6B···O341ii 0.99 2.56 3.4229 (19) 146
C35—H35···O322iii 0.95 2.52 3.4568 (19) 168
