Acta Cryst.(2001). E57, o1075±o1077 DOI: 10.1107/S160053680101618X Zurina Shaameriet al. C54H38N2O8
o1075
organic papers
Acta Crystallographica Section E
Structure Reports
Online ISSN 1600-5368
Diphenic acid±acridine (1/1)
Zurina Shaameri, Ning Shan* and William Jones
Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study T= 295 K
Mean(C±C) = 0.008 AÊ Disorder in main residue Rfactor = 0.064 wRfactor = 0.211
Data-to-parameter ratio = 12.2
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2001 International Union of Crystallography Printed in Great Britain ± all rights reserved
The structure of the title complex, C14H10O4.C13H9N, which was cocrystallized from an ethanol solution containing a 1:1 mixture of diphenic acid and acridine, has been determined. Hydrogen bonding exists between acid±acid and acid±base as well as acridine±interactions. Proton transfer occurs in one of the two carboxylic acid±aromatic nitrogen interactions.
Comment
Diphenic acid (biphenyl-2,20-dicarboxylic acid) forms in®nite zigzag acid chainsvia R22(8) carboxylic acid pairs (Fronczeket
al., 1987). It is of interest since it is potentially a good building block in crystal engineering with organic bases. To date, no organic co-crystal structure involving diphenic acid exists in the Cambridge Structural Database (ConQuest; CCDC 2001). We report here the ®rst diphenic acid cocrystal structure with acridine as the base, (I).
.
The asymmetric unit of complex (I) comprises two acid and two base molecules (Fig. 1). The biphenyl units of the two acid molecules adopt twisted conformations, with the least-squares planes through the two phenyl units forming angles of 72 and 89. A two-acid±two-base unit exists (Fig. 2), involving an O1ÐH01 O4 intramolecular hydrogen bond, an O7Ð H03 O3 acid±acid interaction and several acid±base inter-molecular interactions (Table 2). In one of the two pairs of acid±base contacts, proton transfer occurs from the carboxylic acid group O3ÐC14ÐO4 to aromatic N2, evidenced by the O3ÐC14 and O4ÐC14 bond distances (Table 1). H02, the proton involved in the other acid±base contact (located from a difference map) remains within the carboxylic group attached to O5. The O6 site was re®ned with disorder over two distinct positions (O6A and O6B) with equal occupancy; possible weak hydrogen bonds C40ÐH40 O6A and C40Ð H40 O6B are noted. An in®nite supramolecular unit is formed along the a axis by packing the two-acid±two-base unitsvia±interactions between acridine molecules. Acri-dine molecular planes are approximately perpendicular to the
aaxis, with a distance of approximately 3.5 AÊ between adja-cent planes (Fig. 2). The in®nite supramolecular units assembleviaclose packing (Fig. 3).
Experimental
Diphenic acid and acridine were obtained from Aldrich. 28 mg of the acid and 18 mg of the base were dissolved in 15 ml of ethanol. Crystals were obtained by slow evaporation of the ethanol solution at room temperature.
Crystal data
C14H10O4C14H9O4ÿC13H9NC
13-H10N+
Mr= 842.86
Monoclinic,P21=c
a= 14.461 (3) AÊ
b= 15.863 (3) AÊ
c= 19.166 (3) AÊ = 108.98 (2) V= 4157.5 (13) AÊ3
Z= 4
Dx= 1.347 Mg mÿ3
MoKradiation Cell parameters from 25
re¯ections = 8.0±15.0
= 0.09 mmÿ1
T= 295 (2) K Block, yellow 0.300.300.20 mm
Data collection Enraf±Nonius CAD-4
diffractometer !/2scans
Absorption correction: none 7509 measured re¯ections 7275 independent re¯ections 3160 re¯ections withI> 2(I)
Rint= 0.045
max= 25.0
h=ÿ17!16
k= 0!18
l= 0!22
3 standard re¯ections every 200 re¯ections intensity decay: none
Re®nement Re®nement onF2
R[F2> 2(F2)] = 0.064
wR(F2) = 0.211
S= 1.01 7275 re¯ections 598 parameters
H atoms treated by a mixture of independent and constrained re®nement
w= 1/[2(F
o2) + (0.0914P)2]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.002
max= 0.23 e AÊÿ3
min=ÿ0.25 e AÊÿ3
Table 1
Selected geometric parameters (AÊ,).
O1ÐC13 1.325 (6) O2ÐC13 1.205 (6) O3ÐC14 1.265 (5) O4ÐC14 1.246 (5) O7ÐC28 1.308 (6)
O5ÐC27 1.287 (6) O6AÐC27 1.297 (12) O6BÐC27 1.223 (11) C28ÐO8 1.199 (6)
Table 2
Hydrogen-bonding geometry (AÊ,).
DÐH A DÐH H A D A DÐH A
O1ÐH01 O4 0.84 1.74 2.578 (6) 178 O7ÐH03 O3 0.85 1.75 2.596 (5) 173 O5ÐH02 N1i 0.84 1.86 2.675 (5) 162
C40ÐH40 O6Aii 0.93 2.39 3.258 (14) 155
C40ÐH40 O6Bii 0.93 2.57 3.282 (12) 133
N2ÐH2 O3iii 0.86 1.88 2.734 (5) 177
Symmetry codes: (i) 2ÿx;1
2y;12ÿz; (ii) 2ÿx;yÿ12;12ÿz; (iii) 1ÿx;yÿ12;12ÿz.
Figure 1
The asymmetric unit of (I) showing displacement ellipsoids at the 30% probability level. H atoms bonded to carbon have been omitted for clarity (Sheldrick, 1993).
Figure 2
Owing to large anisotropic displacement parameters, atom O6 was re®ned over two distinct positions with equal ®xed occupation factors (from re®nement).
All H atoms bonded to C atoms were placed geometrically and re®ned using a riding model with the Uisovalues for each H atom
taken as 1.2Ueqof the carrier atom. The O-bound H01, H02 and H03
were located from difference Fourier maps and were included in the model with the OÐH distance restrained to 0.820.02 AÊ. Atom H2 was located from the difference Fourier map and was re®ned using a riding model with theUisovalue taken as 1.2Ueqof N2.
Data collection: CAD-4 Software (Enraf±Nonius, 1988); cell re®nement:CAD-4Software(SETANG); data reduction:TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1993); software used to prepare material for publication: SHELXL97).
We thank the DWEF Cambridge Scholarship and ORS Award for funding (NS).
References
CCDC. (2001).ConQuest. Version 1.2. CCDC, Cambridge, UK.
Enraf±Nonius (1988).CAD-4Software. Version 5.0. Enraf±Nonius, Delft, The Netherlands.
Fronczek, F. R., Davis, S. T., Gehrig, L. M. B. & Gandour, R. D. (1987).Acta Cryst.C43, 1615±1618.
Molecular Structure Corporation (1995). TEXSAN. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
Sheldrick, G. M. (1993).XP. University of GoÈttingen, Germany.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of GoÈttingen, Germany.
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996).CAMERON. Chemical Crystallography Laboratory, University of Oxford, UK.
Acta Cryst.(2001). E57, o1075±o1077 Zurina Shaameriet al. C54H38N2O8
o1077
organic papers
Figure 3
supporting information
Acta Cryst. (2001). E57, o1075–o1077 [doi:10.1107/S160053680101618X]
Diphenic acid
–
acridine (1/1)
Zurina Shaameri, Ning Shan and William Jones
S1. Comment
Diphenic acid (biphenyl-2,2′-dicarboxylic acid), (I), forms infinite zigzag acid chains via R22(8) carboxylic acid pairs
(Fronczek et al., 1987). It is of interest since it is potentially a good building block in crystal engineering with organic
bases. To date, no organic co-crystal structure involving diphenic acid exists in the Cambridge Structural Database
(CONQUEST 1.2, 2001). We report here the first diphenic acid co-crystal structure with acridine as the base.
The asymmetric unit of complex (I) comprises of two acid and two base molecules (Fig. 1). The torsion angles of the
two phenyl rings are approximately 72° and 89°, respectively. A two-acid–two-base unit exists (Fig. 2), involving an O1
—H01···O4 intramolecular hydrogen bond, an O7—H03···O3 acid–acid interaction and several acid–base intermolecular
interactions (Table 2). In one of the two pairs of acid–base contacts, proton transfer occurs from the carboxylic acid
group O3—C14—O4 to aromatic N2, evidenced by the O3—C14 and O4—C14 bond distances (Table 1). H02, the
proton involved in the other acid–base contact (located from the difference map) remains within the carboxylic group
attached to O5. The O6 site was refined with disorder over two distinct positions (O6A & O6B) with equal occupancy,
and possible weak hydrogen bonds C40—H40—O6A and C40—H40—O6B are noted. An infinite supramolecular unit is
formed along the a axis by packing the two-acid–two-base units via π-π interactions between acridine molecules.
Acridine molecular planes are approximately perpendicular to the a axis, with a distance of approximately 3.5 Å between
adjacent planes (Fig. 2). The infinite supramolecular units pack assemble via close packing (Fig. 3).
S2. Experimental
Diphenic acid and acridine were obtained from Aldrich. 28 mg of the acid and 18 mg of the base were dissolved in 15 ml
of ethanol. Crystals were obtained by slow evaporation of the ethanol solution at the room temperature.
S3. Refinement
Owing to large anisotropic displacement parameters, the O6 atom was refined over two distinct positions with equal fixed
occupation factors (from refinement).
All H atoms bonded to C atoms were placed geometrically and refined using a riding model with the Uiso values for each
H atom taken as 1.2 Ueq of the carrier atom. The O-bound H01, H02 and H03 were located from difference Fourier maps
and were included in the model with the O– H distance restrained to 0.82 +/-0.02 Å. The H2 atom was located from the
supporting information
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[image:5.610.127.482.70.325.2]Acta Cryst. (2001). E57, o1075–o1077
Figure 1
The asymmetric unit of (I) showing displacement ellipsoids at the 30% probability level. H atoms bonded to carbon have
Figure 2
Projection of the molecular packing of (I) onto the (010) plane showing the acridine molecules stacked along the a axis.
supporting information
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[image:7.610.125.485.70.458.2]Acta Cryst. (2001). E57, o1075–o1077
Figure 3
Projection onto (100) showing the packing of the infinite supramolecular unit. (Watkin et al., 1996).
Diphenic acid–acridine (1/1)
Crystal data
C14H10O4·C14H9O4−·C13H9N·C13H10N+
Mr = 842.86
Monoclinic, P21/c
a = 14.461 (3) Å b = 15.863 (3) Å c = 19.166 (3) Å β = 108.98 (2)° V = 4157.5 (13) Å3
Z = 4
F(000) = 1760
Dx = 1.347 Mg m−3
Melting point: not measured K Mo Kα radiation, λ = 0.71073 Å Cell parameters from 25 reflections θ = 8.0–15.0°
µ = 0.09 mm−1
T = 295 K Block, yellow
Data collection
Enraf-Nonius CAD-4 diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω/2θ scans
7509 measured reflections 7275 independent reflections 3160 reflections with I > 2σ(I)
Rint = 0.045
θmax = 25.0°, θmin = 3.6°
h = −17→16 k = 0→18 l = 0→22
3 standard reflections every 200 reflections intensity decay: none
Refinement
Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.064
wR(F2) = 0.211
S = 1.01 7275 reflections 598 parameters 3 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) + (0.0914P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.002
Δρmax = 0.23 e Å−3
Δρmin = −0.25 e Å−3
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 Occ. (<1)
H01 0.498 (3) 0.470 (5) 0.208 (3) 0.15 (4)*
O1 0.4420 (3) 0.4601 (2) 0.1793 (2) 0.0636 (10)
O2 0.3023 (3) 0.5244 (2) 0.1240 (2) 0.0708 (11)
O3 0.7697 (2) 0.5046 (2) 0.27410 (16) 0.0540 (9)
O4 0.6161 (3) 0.4858 (2) 0.26916 (18) 0.0632 (10)
C8 0.6443 (3) 0.5338 (3) 0.1611 (2) 0.0427 (11)
C14 0.6786 (4) 0.5062 (3) 0.2403 (2) 0.0465 (12)
C2 0.4360 (3) 0.6095 (3) 0.1934 (2) 0.0444 (11)
C7 0.5678 (3) 0.5905 (3) 0.1335 (2) 0.0366 (10)
C1 0.5214 (3) 0.6365 (3) 0.1817 (2) 0.0406 (11)
C11 0.5836 (4) 0.5761 (3) 0.0127 (3) 0.0524 (13)
H11 0.5621 0.5897 −0.0372 0.063*
C9 0.6905 (4) 0.5006 (3) 0.1131 (3) 0.0521 (12)
H9 0.7435 0.4643 0.1312 0.063*
supporting information
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Acta Cryst. (2001). E57, o1075–o1077
H12 0.4895 0.6506 0.0401 0.057*
C6 0.5609 (4) 0.7140 (3) 0.2107 (3) 0.0551 (13)
H6 0.6170 0.7340 0.2027 0.066*
C10 0.6582 (4) 0.5213 (3) 0.0397 (3) 0.0542 (13)
H10 0.6879 0.4973 0.0081 0.065*
C13 0.3868 (4) 0.5286 (3) 0.1622 (3) 0.0512 (12)
C3 0.3930 (4) 0.6585 (3) 0.2339 (3) 0.0603 (14)
H3 0.3358 0.6402 0.2414 0.072*
C5 0.5163 (5) 0.7615 (3) 0.2515 (3) 0.0713 (17)
H5 0.5432 0.8130 0.2712 0.086*
C4 0.4339 (5) 0.7334 (4) 0.2630 (3) 0.0742 (17)
H4 0.4051 0.7655 0.2910 0.089*
H03 0.861 (3) 0.544 (3) 0.242 (3) 0.08 (2)*
O7 0.9094 (3) 0.5653 (2) 0.2317 (2) 0.0607 (9)
O5 1.1873 (3) 0.5394 (2) 0.2677 (2) 0.0655 (10)
H02 1.228 (5) 0.531 (5) 0.310 (2) 0.16 (4)*
O6A 1.2233 (10) 0.4118 (8) 0.2447 (7) 0.104 (4) 0.50
O6B 1.1697 (9) 0.4049 (7) 0.2685 (7) 0.101 (5) 0.50
C15 1.0219 (3) 0.5484 (3) 0.1355 (2) 0.0458 (12)
C21 1.0477 (3) 0.6347 (3) 0.1661 (2) 0.0439 (11)
C16 1.0725 (3) 0.4755 (3) 0.1634 (2) 0.0441 (11)
C22 0.9903 (4) 0.6801 (3) 0.1990 (2) 0.0516 (13)
C26 1.1275 (4) 0.6757 (3) 0.1567 (3) 0.0573 (13)
H26 1.1657 0.6473 0.1336 0.069*
C17 1.0415 (4) 0.3984 (3) 0.1276 (3) 0.0598 (14)
H17 1.0752 0.3493 0.1469 0.072*
C28 0.9010 (4) 0.6449 (4) 0.2125 (3) 0.0604 (14)
C19 0.9100 (4) 0.4657 (4) 0.0357 (3) 0.0704 (16)
H19 0.8558 0.4630 −0.0068 0.084*
C18 0.9620 (4) 0.3943 (4) 0.0644 (3) 0.0711 (16)
H18 0.9433 0.3428 0.0409 0.085*
O8 0.8293 (3) 0.6857 (3) 0.2072 (3) 0.1088 (17)
C20 0.9394 (4) 0.5413 (4) 0.0711 (3) 0.0634 (15)
H20 0.9038 0.5896 0.0519 0.076*
C27 1.1572 (4) 0.4702 (3) 0.2327 (3) 0.0613 (14)
C23 1.0136 (4) 0.7632 (3) 0.2208 (3) 0.0640 (15)
H23 0.9739 0.7933 0.2415 0.077*
C24 1.0940 (5) 0.8015 (4) 0.2123 (3) 0.0741 (17)
H24 1.1096 0.8568 0.2277 0.089*
C25 1.1517 (4) 0.7566 (4) 0.1804 (3) 0.0732 (17)
H25 1.2073 0.7815 0.1750 0.088*
N1 0.6889 (3) 0.0480 (2) 0.0941 (2) 0.0447 (10)
C41 0.6445 (3) −0.0175 (3) 0.0507 (2) 0.0432 (11)
C36 0.6100 (3) −0.0109 (3) −0.0277 (3) 0.0463 (12)
C29 0.6962 (3) 0.1226 (3) 0.0616 (3) 0.0447 (11)
C35 0.6196 (3) 0.0646 (3) −0.0587 (3) 0.0537 (13)
H35 0.5974 0.0698 −0.1098 0.064*
C40 0.6353 (3) −0.0946 (3) 0.0839 (3) 0.0540 (13)
H40 0.6583 −0.0998 0.1350 0.065*
C30 0.7421 (4) 0.1908 (3) 0.1083 (3) 0.0579 (14)
H30 0.7648 0.1844 0.1593 0.069*
C37 0.5678 (4) −0.0835 (4) −0.0693 (3) 0.0618 (14)
H37 0.5457 −0.0810 −0.1205 0.074*
C38 0.5596 (4) −0.1562 (4) −0.0352 (3) 0.0669 (15)
H38 0.5314 −0.2032 −0.0630 0.080*
C33 0.6719 (4) 0.2141 (4) −0.0451 (3) 0.0612 (14)
H33 0.6485 0.2227 −0.0959 0.073*
C39 0.5931 (4) −0.1610 (3) 0.0414 (3) 0.0671 (15)
H39 0.5862 −0.2114 0.0640 0.081*
C32 0.7150 (4) 0.2776 (3) −0.0002 (4) 0.0700 (16)
H32 0.7205 0.3301 −0.0201 0.084*
C31 0.7521 (4) 0.2659 (3) 0.0766 (4) 0.0705 (16)
H31 0.7840 0.3102 0.1065 0.085*
N2 0.1773 (3) 0.0562 (2) 0.0821 (2) 0.0458 (10)
H2 0.1920 0.0395 0.1271 0.055*
C54 0.1363 (3) −0.0001 (3) 0.0277 (2) 0.0421 (11)
C53 0.1143 (3) −0.0815 (3) 0.0456 (3) 0.0523 (12)
H53 0.1286 −0.0978 0.0945 0.063*
C42 0.1963 (3) 0.1374 (3) 0.0695 (3) 0.0489 (12)
C49 0.1158 (3) 0.0250 (3) −0.0458 (3) 0.0488 (12)
C48 0.1413 (3) 0.1067 (4) −0.0602 (3) 0.0606 (15)
H48 0.1324 0.1229 −0.1086 0.073*
C47 0.1795 (3) 0.1635 (3) −0.0038 (3) 0.0555 (13)
C52 0.0718 (4) −0.1360 (3) −0.0098 (4) 0.0656 (15)
H52 0.0574 −0.1905 0.0014 0.079*
C50 0.0706 (4) −0.0344 (4) −0.1013 (3) 0.0692 (16)
H50 0.0556 −0.0192 −0.1506 0.083*
C46 0.2036 (4) 0.2492 (4) −0.0146 (4) 0.0782 (18)
H46 0.1961 0.2690 −0.0618 0.094*
C45 0.2375 (4) 0.3014 (4) 0.0446 (5) 0.0816 (19)
H45 0.2527 0.3568 0.0368 0.098*
C51 0.0489 (4) −0.1116 (5) −0.0843 (4) 0.0778 (18)
H51 0.0186 −0.1496 −0.1217 0.093*
C43 0.2324 (4) 0.1936 (3) 0.1302 (3) 0.0612 (14)
H43 0.2434 0.1748 0.1782 0.073*
C44 0.2503 (4) 0.2746 (4) 0.1170 (4) 0.0790 (18)
H44 0.2711 0.3127 0.1559 0.095*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
O1 0.067 (3) 0.045 (2) 0.078 (3) −0.007 (2) 0.022 (2) 0.0049 (19)
O2 0.044 (2) 0.092 (3) 0.066 (2) −0.005 (2) 0.0034 (19) −0.008 (2)
O3 0.049 (2) 0.071 (2) 0.0386 (18) 0.0099 (18) 0.0089 (16) 0.0062 (16)
supporting information
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Acta Cryst. (2001). E57, o1075–o1077
C8 0.050 (3) 0.038 (3) 0.038 (3) −0.003 (2) 0.012 (2) −0.004 (2)
C14 0.060 (3) 0.039 (3) 0.041 (3) 0.017 (2) 0.017 (3) 0.002 (2)
C2 0.050 (3) 0.047 (3) 0.035 (2) 0.007 (2) 0.012 (2) −0.003 (2)
C7 0.041 (3) 0.035 (2) 0.033 (2) −0.005 (2) 0.011 (2) 0.000 (2)
C1 0.045 (3) 0.039 (3) 0.033 (2) 0.005 (2) 0.006 (2) 0.000 (2)
C11 0.054 (3) 0.071 (3) 0.031 (3) −0.016 (3) 0.013 (2) 0.002 (2)
C9 0.057 (3) 0.051 (3) 0.049 (3) 0.002 (2) 0.017 (3) −0.007 (2)
C12 0.049 (3) 0.046 (3) 0.045 (3) −0.006 (2) 0.011 (2) 0.004 (2)
C6 0.056 (3) 0.050 (3) 0.053 (3) 0.004 (3) 0.009 (3) −0.003 (3)
C10 0.052 (3) 0.072 (4) 0.043 (3) −0.015 (3) 0.022 (3) −0.011 (3)
C13 0.058 (3) 0.058 (3) 0.045 (3) 0.001 (3) 0.028 (3) 0.003 (3)
C3 0.058 (3) 0.072 (4) 0.046 (3) 0.023 (3) 0.010 (3) −0.006 (3)
C5 0.077 (4) 0.052 (3) 0.068 (4) 0.007 (3) 0.001 (3) −0.020 (3)
C4 0.069 (4) 0.083 (5) 0.060 (4) 0.029 (4) 0.006 (3) −0.021 (3)
O7 0.054 (2) 0.069 (3) 0.058 (2) 0.006 (2) 0.0176 (19) 0.0089 (19)
O5 0.073 (3) 0.054 (2) 0.052 (2) 0.010 (2) −0.004 (2) −0.004 (2)
O6A 0.125 (11) 0.067 (8) 0.083 (8) 0.037 (8) −0.017 (7) −0.015 (6)
O6B 0.118 (11) 0.047 (6) 0.084 (8) −0.025 (7) −0.040 (7) 0.035 (6)
C15 0.040 (3) 0.063 (3) 0.035 (3) 0.001 (2) 0.013 (2) −0.006 (2)
C21 0.043 (3) 0.049 (3) 0.034 (2) 0.008 (2) 0.005 (2) 0.009 (2)
C16 0.043 (3) 0.049 (3) 0.039 (3) −0.002 (2) 0.011 (2) 0.004 (2)
C22 0.055 (3) 0.049 (3) 0.045 (3) 0.008 (3) 0.009 (3) 0.008 (2)
C26 0.048 (3) 0.060 (4) 0.061 (3) 0.007 (3) 0.014 (3) 0.011 (3)
C17 0.068 (4) 0.053 (3) 0.056 (3) −0.003 (3) 0.015 (3) −0.006 (3)
C28 0.070 (4) 0.064 (4) 0.049 (3) 0.016 (3) 0.020 (3) −0.002 (3)
C19 0.048 (3) 0.093 (5) 0.062 (4) 0.000 (3) 0.007 (3) −0.025 (4)
C18 0.070 (4) 0.077 (4) 0.067 (4) −0.022 (3) 0.023 (3) −0.029 (3)
O8 0.094 (3) 0.081 (3) 0.177 (5) 0.035 (3) 0.079 (3) 0.014 (3)
C20 0.051 (3) 0.076 (4) 0.061 (3) 0.016 (3) 0.015 (3) −0.010 (3)
C27 0.082 (4) 0.043 (3) 0.049 (3) 0.002 (3) 0.007 (3) −0.003 (3)
C23 0.080 (4) 0.047 (3) 0.056 (3) 0.009 (3) 0.009 (3) 0.006 (3)
C24 0.092 (5) 0.045 (3) 0.072 (4) 0.004 (3) 0.009 (4) 0.007 (3)
C25 0.066 (4) 0.062 (4) 0.081 (4) −0.006 (3) 0.010 (3) 0.030 (3)
N1 0.041 (2) 0.047 (2) 0.045 (2) −0.0024 (19) 0.0120 (19) −0.0049 (19)
C41 0.030 (2) 0.052 (3) 0.047 (3) −0.006 (2) 0.011 (2) −0.005 (2)
C36 0.031 (2) 0.055 (3) 0.048 (3) −0.002 (2) 0.006 (2) −0.006 (3)
C29 0.037 (3) 0.046 (3) 0.051 (3) 0.003 (2) 0.015 (2) 0.000 (2)
C35 0.039 (3) 0.069 (4) 0.046 (3) 0.004 (3) 0.003 (2) 0.001 (3)
C34 0.030 (2) 0.055 (3) 0.054 (3) 0.009 (2) 0.010 (2) 0.007 (3)
C40 0.050 (3) 0.058 (3) 0.055 (3) −0.015 (3) 0.018 (3) −0.003 (3)
C30 0.063 (3) 0.051 (3) 0.057 (3) −0.001 (3) 0.016 (3) −0.003 (3)
C37 0.051 (3) 0.076 (4) 0.054 (3) 0.000 (3) 0.010 (3) −0.009 (3)
C38 0.052 (3) 0.070 (4) 0.075 (4) −0.019 (3) 0.015 (3) −0.026 (3)
C33 0.053 (3) 0.071 (4) 0.058 (3) 0.014 (3) 0.015 (3) 0.021 (3)
C39 0.055 (3) 0.058 (4) 0.083 (4) −0.016 (3) 0.015 (3) −0.003 (3)
C32 0.068 (4) 0.046 (3) 0.096 (5) 0.010 (3) 0.027 (4) 0.020 (3)
C31 0.073 (4) 0.044 (3) 0.092 (5) 0.000 (3) 0.024 (4) −0.003 (3)
C54 0.032 (2) 0.053 (3) 0.039 (3) 0.008 (2) 0.008 (2) 0.000 (2)
C53 0.046 (3) 0.050 (3) 0.057 (3) 0.007 (2) 0.011 (3) 0.000 (3)
C42 0.037 (3) 0.049 (3) 0.061 (3) 0.003 (2) 0.016 (2) 0.013 (3)
C49 0.031 (2) 0.073 (4) 0.043 (3) 0.002 (2) 0.012 (2) −0.005 (3)
C48 0.044 (3) 0.093 (4) 0.044 (3) 0.013 (3) 0.013 (3) 0.027 (3)
C47 0.037 (3) 0.061 (3) 0.067 (4) 0.008 (3) 0.014 (3) 0.018 (3)
C52 0.046 (3) 0.053 (3) 0.098 (5) 0.000 (3) 0.024 (3) −0.014 (3)
C50 0.049 (3) 0.106 (5) 0.055 (3) 0.010 (4) 0.019 (3) −0.014 (4)
C46 0.061 (4) 0.079 (4) 0.094 (5) 0.014 (4) 0.025 (4) 0.038 (4)
C45 0.055 (4) 0.059 (4) 0.122 (6) 0.001 (3) 0.018 (4) 0.023 (4)
C51 0.055 (4) 0.096 (5) 0.075 (5) 0.002 (4) 0.012 (3) −0.040 (4)
C43 0.057 (3) 0.056 (4) 0.065 (4) −0.004 (3) 0.012 (3) −0.004 (3)
C44 0.064 (4) 0.059 (4) 0.102 (5) 0.004 (3) 0.010 (4) −0.002 (4)
Geometric parameters (Å, º)
O1—C13 1.325 (6) C24—C25 1.382 (8)
O1—H01 0.84 (5) C24—H24 0.9300
O2—C13 1.205 (6) C25—H25 0.9300
O3—C14 1.265 (5) N1—C41 1.355 (5)
O4—C14 1.246 (5) N1—C29 1.357 (5)
C8—C7 1.391 (6) C41—C40 1.405 (6)
C8—C9 1.404 (6) C41—C36 1.424 (6)
C8—C14 1.500 (6) C36—C35 1.364 (6)
C2—C3 1.381 (6) C36—C37 1.420 (7)
C2—C1 1.393 (6) C29—C34 1.417 (6)
C2—C13 1.495 (6) C29—C30 1.423 (6)
C7—C12 1.393 (6) C35—C34 1.389 (6)
C7—C1 1.497 (6) C35—H35 0.9300
C1—C6 1.393 (6) C34—C33 1.415 (7)
C11—C10 1.351 (7) C40—C39 1.350 (7)
C11—C12 1.369 (6) C40—H40 0.9300
C11—H11 0.9300 C30—C31 1.366 (7)
C9—C10 1.371 (6) C30—H30 0.9300
C9—H9 0.9300 C37—C38 1.349 (7)
C12—H12 0.9300 C37—H37 0.9300
C6—C5 1.385 (7) C38—C39 1.390 (7)
C6—H6 0.9300 C38—H38 0.9300
C10—H10 0.9300 C33—C32 1.340 (7)
C3—C4 1.364 (7) C33—H33 0.9300
C3—H3 0.9300 C39—H39 0.9300
C5—C4 1.356 (8) C32—C31 1.406 (7)
C5—H5 0.9300 C32—H32 0.9300
C4—H4 0.9300 C31—H31 0.9300
O7—C28 1.308 (6) N2—C54 1.354 (5)
O7—H03 0.85 (5) N2—C42 1.355 (6)
O5—C27 1.287 (6) N2—H2 0.8600
supporting information
sup-10
Acta Cryst. (2001). E57, o1075–o1077
O6A—C27 1.297 (12) C54—C53 1.400 (6)
O6B—C27 1.223 (11) C53—C52 1.350 (7)
C15—C16 1.381 (6) C53—H53 0.9300
C15—C20 1.415 (6) C42—C47 1.408 (7)
C15—C21 1.489 (6) C42—C43 1.423 (7)
C21—C26 1.385 (6) C49—C48 1.399 (7)
C21—C22 1.394 (6) C49—C50 1.411 (7)
C16—C17 1.402 (6) C48—C47 1.377 (7)
C16—C27 1.487 (7) C48—H48 0.9300
C22—C23 1.392 (7) C47—C46 1.436 (8)
C22—C28 1.505 (7) C52—C51 1.412 (8)
C26—C25 1.369 (7) C52—H52 0.9300
C26—H26 0.9300 C50—C51 1.330 (8)
C17—C18 1.373 (7) C50—H50 0.9300
C17—H17 0.9300 C46—C45 1.360 (8)
C28—O8 1.199 (6) C46—H46 0.9300
C19—C18 1.371 (7) C45—C44 1.406 (8)
C19—C20 1.375 (7) C45—H45 0.9300
C19—H19 0.9300 C51—H51 0.9300
C18—H18 0.9300 C43—C44 1.352 (7)
C20—H20 0.9300 C43—H43 0.9300
C23—C24 1.367 (7) C44—H44 0.9300
C23—H23 0.9300
C13—O1—H01 113 (5) C25—C24—H24 120.5
C7—C8—C9 118.8 (4) C26—C25—C24 120.2 (5)
C7—C8—C14 122.3 (4) C26—C25—H25 119.9
C9—C8—C14 118.9 (4) C24—C25—H25 119.9
O4—C14—O3 123.6 (4) C41—N1—C29 118.6 (4)
O4—C14—C8 118.4 (4) N1—C41—C40 119.0 (4)
O3—C14—C8 118.0 (4) N1—C41—C36 121.7 (4)
C3—C2—C1 120.2 (5) C40—C41—C36 119.3 (4)
C3—C2—C13 117.7 (4) C35—C36—C37 123.6 (5)
C1—C2—C13 122.1 (4) C35—C36—C41 118.2 (4)
C8—C7—C12 118.6 (4) C37—C36—C41 118.2 (5)
C8—C7—C1 122.7 (4) N1—C29—C34 122.6 (4)
C12—C7—C1 118.4 (4) N1—C29—C30 117.6 (4)
C2—C1—C6 118.5 (4) C34—C29—C30 119.8 (4)
C2—C1—C7 123.3 (4) C36—C35—C34 121.8 (5)
C6—C1—C7 117.9 (4) C36—C35—H35 119.1
C10—C11—C12 120.0 (4) C34—C35—H35 119.1
C10—C11—H11 120.0 C35—C34—C33 124.1 (5)
C12—C11—H11 120.0 C35—C34—C29 117.1 (4)
C10—C9—C8 120.5 (5) C33—C34—C29 118.9 (5)
C10—C9—H9 119.8 C39—C40—C41 119.8 (5)
C8—C9—H9 119.8 C39—C40—H40 120.1
C11—C12—C7 121.4 (4) C41—C40—H40 120.1
C7—C12—H12 119.3 C31—C30—H30 120.7
C5—C6—C1 119.9 (5) C29—C30—H30 120.7
C5—C6—H6 120.0 C38—C37—C36 120.7 (5)
C1—C6—H6 120.0 C38—C37—H37 119.6
C11—C10—C9 120.7 (5) C36—C37—H37 119.6
C11—C10—H10 119.7 C37—C38—C39 120.2 (5)
C9—C10—H10 119.7 C37—C38—H38 119.9
O2—C13—O1 121.1 (5) C39—C38—H38 119.9
O2—C13—C2 123.2 (5) C32—C33—C34 120.5 (5)
O1—C13—C2 115.8 (4) C32—C33—H33 119.7
C4—C3—C2 120.3 (5) C34—C33—H33 119.7
C4—C3—H3 119.8 C40—C39—C38 121.8 (5)
C2—C3—H3 119.8 C40—C39—H39 119.1
C4—C5—C6 120.6 (5) C38—C39—H39 119.1
C4—C5—H5 119.7 C33—C32—C31 120.8 (5)
C6—C5—H5 119.7 C33—C32—H32 119.6
C5—C4—C3 120.5 (5) C31—C32—H32 119.6
C5—C4—H4 119.8 C30—C31—C32 121.5 (5)
C3—C4—H4 119.8 C30—C31—H31 119.3
C28—O7—H03 116 (4) C32—C31—H31 119.3
C27—O5—H02 112 (6) C54—N2—C42 123.5 (4)
C16—C15—C20 117.5 (4) C54—N2—H2 118.2
C16—C15—C21 125.8 (4) C42—N2—H2 118.2
C20—C15—C21 116.7 (4) N2—C54—C49 119.0 (4)
C26—C21—C22 117.4 (5) N2—C54—C53 119.8 (4)
C26—C21—C15 119.6 (4) C49—C54—C53 121.2 (5)
C22—C21—C15 122.8 (4) C52—C53—C54 118.7 (5)
C15—C16—C17 119.7 (4) C52—C53—H53 120.7
C15—C16—C27 124.9 (4) C54—C53—H53 120.7
C17—C16—C27 115.3 (4) N2—C42—C47 118.6 (5)
C23—C22—C21 120.2 (5) N2—C42—C43 119.4 (4)
C23—C22—C28 115.9 (5) C47—C42—C43 122.0 (5)
C21—C22—C28 123.8 (5) C48—C49—C54 118.6 (5)
C25—C26—C21 122.1 (5) C48—C49—C50 123.8 (5)
C25—C26—H26 118.9 C54—C49—C50 117.6 (5)
C21—C26—H26 118.9 C47—C48—C49 121.0 (4)
C18—C17—C16 121.1 (5) C47—C48—H48 119.5
C18—C17—H17 119.5 C49—C48—H48 119.5
C16—C17—H17 119.5 C48—C47—C42 119.1 (5)
O8—C28—O7 122.9 (5) C48—C47—C46 124.1 (5)
O8—C28—C22 123.5 (5) C42—C47—C46 116.8 (5)
O7—C28—C22 113.6 (5) C53—C52—C51 121.0 (5)
C18—C19—C20 118.7 (5) C53—C52—H52 119.5
C18—C19—H19 120.6 C51—C52—H52 119.5
C20—C19—H19 120.6 C51—C50—C49 121.2 (6)
C19—C18—C17 120.5 (5) C51—C50—H50 119.4
C19—C18—H18 119.8 C49—C50—H50 119.4
supporting information
sup-12
Acta Cryst. (2001). E57, o1075–o1077
C19—C20—C15 122.5 (5) C45—C46—H46 120.1
C19—C20—H20 118.7 C47—C46—H46 120.1
C15—C20—H20 118.7 C46—C45—C44 122.3 (6)
O6B—C27—O5 117.8 (7) C46—C45—H45 118.8
O6B—C27—O6A 47.9 (6) C44—C45—H45 118.8
O5—C27—O6A 114.3 (8) C50—C51—C52 120.3 (5)
O6B—C27—C16 118.5 (7) C50—C51—H51 119.9
O5—C27—C16 117.3 (5) C52—C51—H51 119.9
O6A—C27—C16 123.0 (7) C44—C43—C42 118.9 (5)
C24—C23—C22 121.1 (5) C44—C43—H43 120.5
C24—C23—H23 119.4 C42—C43—H43 120.5
C22—C23—H23 119.4 C43—C44—C45 120.1 (6)
C23—C24—C25 118.9 (5) C43—C44—H44 120.0
C23—C24—H24 120.5 C45—C44—H44 120.0
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
O1—H01···O4 0.84 1.74 2.578 (6) 178
O7—H03···O3 0.85 1.75 2.596 (5) 173
O5—H02···N1i 0.84 1.86 2.675 (5) 162
C40—H40···O6Aii 0.93 2.39 3.258 (14) 155
C40—H40···O6Bii 0.93 2.57 3.282 (12) 133
N2—H2···O3iii 0.86 1.88 2.734 (5) 177
