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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3132–o3133.
Published online 2009 November 21. doi:  10.1107/S1600536809047941
PMCID: PMC2971840

Mutual prodrug of cephazolin and benzydamin: 3-[(1-benzyl-1H-indazol-3-yl)­oxy]-N,N-dimethyl­propan-1-aminium 3-{[(5-methyl-1,3,4-thia­diazol-2-yl)sulfan­yl]meth­yl}-8-oxo-7-[(1H-tetra­zol-1-yl)acetamido]-5-thia-1-aza­bicyclo­[4.2.0]octane-2-carboxyl­ate (benzydaminium cephazolinate)

Abstract

In the crystal of the title mol­ecular salt, C19H24N3O+·C14H13N8O4S3 , the cations and anions are linked by N—H(...)O hydrogen bonds. Short intra­molecular C—H(...)O contacts occur within the anion and inter­molecular C—H(...)O and C—H(...)π bonds help to establish the packing.

Related literature

Cephazolin, is a first generation cefalosporin antibiotic and benzydamin hydrochloride is a locally acting non-steroidal anti-inflammatory drug with local anaesthetic and analgesic properties. The title compound was prepared as a mutual prodrug for the treatment of infections and inflamatory conditions. For medicinal background to cephazolin, see: Turnbull (1995 [triangle]). For ring-puckering analysis, see: Cremer & Pople (1975 [triangle]). For graph-set theory, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o3132-scheme1.jpg

Experimental

Crystal data

  • C19H24N3O+·C14H13N8O4S3
  • M r = 763.92
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3132-efi1.jpg
  • a = 44.409 (3) Å
  • b = 7.1777 (5) Å
  • c = 11.2683 (8) Å
  • β = 90.587 (8)°
  • V = 3591.6 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 296 K
  • 0.24 × 0.14 × 0.12 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.957, T max = 0.968
  • 34321 measured reflections
  • 6750 independent reflections
  • 4092 reflections with I > 2σ(I)
  • R int = 0.088

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.095
  • S = 1.00
  • 6750 reflections
  • 475 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.36 e Å−3
  • Δρmin = −0.23 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 2918 Friedel Pairs
  • Flack parameter: −0.07 (7)

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809047941/hb5219sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809047941/hb5219Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

AA gratefully acknowledges the Higher Education Commision, Islamabad, Pakistan, for providing a Scholaship under the Indigenous PhD Program.

supplementary crystallographic information

Comment

Cephazolin, is a first generation cefalosporin antibiotic and benzydamin hydrochloride is a locally acting nonsteroidal anti-inflammatory drug with local anaesthetic and analgesic properties providing both rapid and extended pain relief as well as a significant anti-inflammatory treatment for the painful inflammatory conditions of mouth and throat (Turnbull, 1995). The title compound (I, Fig. 1) was prepared as a mutual prodrug for the treatment of infections and inflamatory conditions.

No crystal structure has been found related to cation. In the cation the indazol moiety A (C1–C6/N2/N1/C14) and the benzene ring B (C8–C13) are planar with r.m.s. deviations of 0.0258 and 0.0031 Å respectively, from the respective mean square planes. The dihedral angle between A/B is 71.06 (12)°. In this cation, there exist an intramolecular H-bonding of C—H···O type (Table 1, Fig. 1) forming S(5) ring motif (Bernstein et al., 1995) in the envelop form.

In the anion, two five membered heterocyclic rings C (C25/S3/C26/N5/N4) and D (N8—N9/C33) are planar with r. m. s. deviations of 0.0025 and 0.0014 Å respectively, from the respective mean square planes and the dihedral angle between C/D is 38.58 (14)°. The heterocyclic six membered E (C20/C21/C22/N6/C28/S1) is in the twisted form, with the maximum puckering amplitude QT = 0.623 (4) Å (Cremer & Pople, 1975) and the four membered ring F (N6/C28–C30) is not planar also. In anion, there exist two S(5) and a S(6) ring motifs (Table 1, Fig. 1). The molecules are stabilized in the form of polymeric chains forming R21(6), R42(8), R22(10) and other ring motifs (Fig. 2 & Fig. 3).

Experimental

Cefazolin sodium (0.238 g; 0.1 mol) and benzydamine hydrochloride (0.173 g; 0.01 mol) were dissolved separately in distilled water (50 ml). Ten milliliter of each solution were mixed and left for two days. The colourless needles of (I) thus obtained were filtered out by suction, washed with distilled water and dried under vacuum.

Refinement

The coordinates of H3N were refined. The H-atoms were positioned geometrically (O–H = 0.82 Å, N–H = 0.86 Å, C–H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier) or 1.5Ueq(methyl C).

Figures

Fig. 1.
View of (I) with displacement ellipsoids drawn at the 30% probability level.
Fig. 2.
The partial packing of (I), which shows that molecules form polymeric chains and ring motifs.
Fig. 3.
The partial packing of (I), which shows that molecules form polymeric networks with various ring motifs.

Crystal data

C19H24N3O+·C14H13N8O4S3F(000) = 1600
Mr = 763.92Dx = 1.413 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 3824 reflections
a = 44.409 (3) Åθ = 2.6–26.0°
b = 7.1777 (5) ŵ = 0.27 mm1
c = 11.2683 (8) ÅT = 296 K
β = 90.587 (8)°Cut needle, colourless
V = 3591.6 (4) Å30.24 × 0.14 × 0.12 mm
Z = 4

Data collection

Bruker Kappa APEXII CCD diffractometer6750 independent reflections
Radiation source: fine-focus sealed tube4092 reflections with I > 2σ(I)
graphiteRint = 0.088
Detector resolution: 7.60 pixels mm-1θmax = 26.0°, θmin = 2.6°
ω scansh = −54→54
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −8→8
Tmin = 0.957, Tmax = 0.968l = −13→13
34321 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095w = 1/[σ2(Fo2) + (0.0342P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
6750 reflectionsΔρmax = 0.36 e Å3
475 parametersΔρmin = −0.23 e Å3
1 restraintAbsolute structure: Flack (1983), 2918 Friedal Pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.07 (7)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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)

xyzUiso*/Ueq
O10.14103 (6)0.2863 (4)0.9240 (3)0.0552 (11)
N10.18241 (7)0.2542 (4)0.7971 (3)0.0420 (12)
N20.19416 (7)0.3698 (5)0.7111 (3)0.0433 (12)
N30.06627 (7)0.0749 (5)1.1012 (3)0.0372 (11)
C10.15436 (8)0.5181 (5)0.7788 (3)0.0340 (12)
C20.13236 (9)0.6570 (6)0.7813 (4)0.0510 (17)
C30.13442 (11)0.8000 (7)0.7038 (4)0.0640 (17)
C40.15844 (11)0.8115 (6)0.6251 (4)0.0610 (19)
C50.18016 (10)0.6769 (6)0.6189 (3)0.0490 (17)
C60.17762 (8)0.5263 (5)0.6969 (3)0.0370 (12)
C70.21920 (9)0.3080 (6)0.6398 (3)0.0463 (17)
C80.24923 (8)0.3866 (5)0.6760 (3)0.0353 (12)
C90.25878 (9)0.3855 (6)0.7933 (4)0.0466 (17)
C100.28704 (10)0.4478 (6)0.8244 (4)0.0520 (17)
C110.30587 (9)0.5147 (6)0.7391 (4)0.0484 (17)
C120.29672 (9)0.5182 (6)0.6231 (4)0.0492 (17)
C130.26851 (9)0.4546 (6)0.5911 (3)0.0450 (17)
C140.15916 (9)0.3469 (5)0.8366 (3)0.0393 (16)
C150.14483 (9)0.1004 (6)0.9660 (4)0.0546 (17)
C160.12086 (10)0.0662 (8)1.0548 (4)0.0699 (19)
C170.09024 (9)0.0869 (7)1.0079 (4)0.0636 (19)
C180.06411 (12)0.2420 (7)1.1765 (4)0.089 (3)
C190.03700 (9)0.0436 (8)1.0420 (4)0.0718 (19)
S10.10575 (2)0.19304 (14)0.49823 (9)0.0428 (3)
S20.14745 (2)0.56694 (16)0.18123 (9)0.0463 (4)
S30.20738 (2)0.44836 (15)0.08659 (9)0.0456 (4)
O20.05024 (6)0.8249 (3)0.3777 (2)0.0384 (9)
O30.08047 (6)0.7715 (4)0.2253 (2)0.0547 (11)
O40.02066 (6)0.4136 (4)0.3861 (2)0.0405 (9)
O50.02552 (7)0.0728 (4)0.7592 (2)0.0587 (13)
N40.19862 (7)0.4956 (4)0.3076 (3)0.0406 (12)
N50.22865 (7)0.4435 (4)0.2966 (3)0.0427 (12)
N60.06812 (6)0.4815 (4)0.4717 (2)0.0279 (10)
N70.03965 (6)0.0819 (4)0.5676 (2)0.0315 (10)
N80.02949 (7)−0.3125 (4)0.7545 (3)0.0325 (11)
N90.05801 (8)−0.3400 (5)0.7855 (3)0.0603 (16)
N100.05818 (10)−0.4303 (7)0.8833 (4)0.0751 (17)
N110.02978 (11)−0.4641 (5)0.9184 (3)0.0663 (16)
C200.13044 (8)0.3791 (5)0.4529 (3)0.0440 (14)
C210.11584 (8)0.5428 (5)0.3900 (3)0.0317 (12)
C220.08645 (8)0.5831 (5)0.3948 (3)0.0293 (12)
C230.07099 (9)0.7410 (5)0.3273 (3)0.0330 (12)
C240.13782 (8)0.6622 (5)0.3251 (3)0.0396 (14)
C250.18490 (8)0.5045 (5)0.2061 (3)0.0376 (12)
C260.23635 (9)0.4134 (5)0.1884 (3)0.0407 (14)
C270.26722 (9)0.3571 (6)0.1520 (4)0.0570 (17)
C280.07883 (8)0.3496 (5)0.5621 (3)0.0347 (12)
C290.04609 (8)0.2771 (5)0.5704 (3)0.0323 (12)
C300.04024 (8)0.3968 (5)0.4591 (3)0.0289 (12)
C310.02943 (8)−0.0044 (5)0.6644 (3)0.0340 (12)
C320.02179 (8)−0.2078 (5)0.6480 (3)0.0337 (12)
C330.01254 (10)−0.3891 (5)0.8368 (4)0.0479 (17)
H20.116640.651240.835130.0612*
H30.119650.891900.702790.0762*
H3N0.0701 (8)−0.035 (5)1.148 (3)0.0446*
H40.159710.914340.575200.0732*
H50.195890.685140.565330.0588*
H7A0.215210.341640.557780.0555*
H7B0.220300.173140.643810.0555*
H90.245920.342000.851740.0560*
H100.293340.444580.903360.0622*
H110.324940.557740.760190.0578*
H120.309600.563740.565400.0593*
H130.262440.457590.511900.0541*
H15A0.164580.085571.002360.0653*
H15B0.142990.012810.900750.0653*
H16A0.12321−0.059021.085890.0837*
H16B0.123640.152301.120350.0837*
H17A0.08661−0.009320.949050.0766*
H17B0.088600.206480.968210.0766*
H18A0.059500.348341.127960.1331*
H18B0.082950.261811.217100.1331*
H18C0.048460.224781.233660.1331*
H19A0.032480.146820.990690.1076*
H19B0.021590.032371.100700.1076*
H19C0.03785−0.068900.996050.1076*
H7N0.042370.019750.503380.0378*
H20A0.140870.425650.522880.0529*
H20B0.145520.326940.400830.0529*
H24A0.156020.674920.372700.0474*
H24B0.129270.785430.314260.0474*
H27A0.277080.293760.216630.0852*
H27B0.278580.465980.131340.0852*
H27C0.265900.275440.084740.0852*
H280.086070.410030.635030.0418*
H290.036220.334030.638840.0385*
H32A0.00044−0.220750.630990.0402*
H32B0.03281−0.257360.581210.0402*
H33−0.00840−0.389520.836620.0575*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.058 (2)0.0430 (17)0.065 (2)0.0076 (15)0.0274 (16)0.0174 (15)
N10.036 (2)0.044 (2)0.046 (2)0.0012 (17)0.0080 (18)0.0076 (17)
N20.031 (2)0.052 (2)0.047 (2)0.0036 (18)0.0123 (17)0.0080 (18)
N30.039 (2)0.043 (2)0.0295 (19)0.0030 (18)0.0015 (16)0.0090 (17)
C10.030 (2)0.037 (2)0.035 (2)−0.0035 (19)−0.0037 (19)0.0030 (19)
C20.049 (3)0.050 (3)0.054 (3)0.008 (2)0.007 (2)0.009 (2)
C30.070 (3)0.064 (3)0.058 (3)0.021 (3)0.005 (3)0.014 (3)
C40.082 (4)0.048 (3)0.053 (3)0.003 (3)0.002 (3)0.013 (2)
C50.054 (3)0.054 (3)0.039 (3)−0.015 (3)0.001 (2)0.010 (2)
C60.034 (2)0.040 (2)0.037 (2)−0.006 (2)−0.004 (2)0.002 (2)
C70.042 (3)0.051 (3)0.046 (3)−0.002 (2)0.006 (2)−0.003 (2)
C80.034 (2)0.036 (2)0.036 (2)0.0023 (19)0.005 (2)0.003 (2)
C90.049 (3)0.049 (3)0.042 (3)−0.007 (2)0.008 (2)0.001 (2)
C100.059 (3)0.056 (3)0.041 (3)−0.008 (3)−0.005 (2)−0.002 (2)
C110.040 (3)0.042 (3)0.063 (3)0.007 (2)−0.003 (2)0.000 (2)
C120.041 (3)0.052 (3)0.055 (3)0.004 (2)0.014 (2)0.009 (2)
C130.042 (3)0.051 (3)0.042 (3)0.004 (2)0.006 (2)0.004 (2)
C140.031 (2)0.047 (3)0.040 (3)−0.006 (2)0.006 (2)0.009 (2)
C150.042 (3)0.054 (3)0.068 (3)0.005 (2)0.010 (2)0.015 (3)
C160.054 (3)0.071 (3)0.085 (4)0.004 (3)0.023 (3)0.042 (3)
C170.051 (3)0.082 (4)0.058 (3)−0.010 (3)0.006 (3)0.024 (3)
C180.128 (5)0.061 (4)0.077 (4)0.019 (3)−0.010 (4)−0.030 (3)
C190.052 (3)0.101 (4)0.062 (3)−0.009 (3)−0.015 (2)0.006 (3)
S10.0374 (6)0.0314 (5)0.0596 (7)0.0060 (5)0.0004 (5)0.0109 (5)
S20.0375 (6)0.0565 (7)0.0448 (7)−0.0009 (6)0.0007 (5)0.0019 (6)
S30.0463 (7)0.0527 (7)0.0380 (6)0.0001 (6)0.0054 (5)−0.0031 (5)
O20.0384 (16)0.0316 (15)0.0452 (17)0.0089 (13)0.0084 (14)0.0012 (13)
O30.067 (2)0.0582 (19)0.0393 (17)0.0184 (16)0.0200 (16)0.0246 (15)
O40.0324 (15)0.0485 (17)0.0406 (16)−0.0028 (13)−0.0041 (14)0.0086 (14)
O50.106 (3)0.0393 (17)0.0313 (16)−0.0094 (17)0.0191 (16)−0.0010 (15)
N40.037 (2)0.046 (2)0.039 (2)0.0003 (16)0.0038 (16)0.0039 (16)
N50.038 (2)0.047 (2)0.043 (2)0.0016 (18)0.0012 (17)0.0032 (18)
N60.0282 (18)0.0253 (17)0.0302 (17)−0.0001 (14)0.0004 (14)0.0099 (14)
N70.0414 (19)0.0239 (17)0.0293 (18)−0.0033 (15)0.0101 (15)0.0011 (15)
N80.038 (2)0.0287 (16)0.0308 (19)−0.0024 (16)0.0055 (16)0.0022 (16)
N90.044 (2)0.080 (3)0.057 (3)0.010 (2)0.000 (2)0.016 (2)
N100.074 (3)0.090 (3)0.061 (3)0.028 (3)−0.009 (2)0.022 (3)
N110.096 (3)0.059 (3)0.044 (2)0.001 (3)0.003 (2)0.020 (2)
C200.036 (2)0.043 (2)0.053 (3)−0.003 (2)0.000 (2)0.011 (2)
C210.031 (2)0.027 (2)0.037 (2)−0.0021 (18)0.0007 (18)0.0008 (18)
C220.030 (2)0.028 (2)0.030 (2)−0.0067 (18)0.0040 (17)0.0024 (18)
C230.036 (2)0.028 (2)0.035 (2)−0.0032 (18)−0.005 (2)0.0028 (19)
C240.035 (2)0.034 (2)0.050 (3)−0.0034 (19)0.0070 (19)0.004 (2)
C250.040 (2)0.035 (2)0.038 (2)−0.0023 (19)0.007 (2)0.0035 (19)
C260.037 (2)0.041 (2)0.044 (3)−0.001 (2)0.003 (2)−0.003 (2)
C270.044 (3)0.062 (3)0.065 (3)0.006 (2)0.008 (2)0.001 (2)
C280.039 (2)0.035 (2)0.030 (2)0.0001 (19)0.0014 (19)0.0055 (18)
C290.039 (2)0.029 (2)0.029 (2)0.0000 (19)0.0081 (18)0.0008 (18)
C300.029 (2)0.029 (2)0.029 (2)0.0037 (19)0.0095 (19)−0.0001 (18)
C310.036 (2)0.036 (2)0.030 (2)−0.0018 (19)0.0035 (19)0.0063 (19)
C320.036 (2)0.033 (2)0.032 (2)−0.0091 (18)0.0000 (18)0.0061 (18)
C330.055 (3)0.048 (3)0.041 (3)−0.007 (2)0.009 (2)0.008 (2)

Geometric parameters (Å, °)

S1—C201.805 (4)C11—C121.365 (6)
S1—C281.797 (4)C12—C131.378 (6)
S2—C241.815 (4)C15—C161.489 (6)
S2—C251.742 (4)C16—C171.461 (6)
S3—C261.733 (4)C2—H20.9300
S3—C251.732 (4)C3—H30.9300
O1—C151.425 (5)C4—H40.9300
O1—C141.350 (5)C5—H50.9300
O2—C231.243 (5)C7—H7B0.9700
O3—C231.247 (4)C7—H7A0.9700
O4—C301.197 (4)C9—H90.9300
O5—C311.217 (4)C10—H100.9300
N1—N21.382 (5)C11—H110.9300
N1—C141.310 (5)C12—H120.9300
N2—C71.448 (5)C13—H130.9300
N2—C61.351 (5)C15—H15B0.9700
N3—C171.506 (5)C15—H15A0.9700
N3—C181.473 (6)C16—H16A0.9700
N3—C191.472 (5)C16—H16B0.9700
N3—H3N0.96 (4)C17—H17A0.9700
N4—N51.392 (4)C17—H17B0.9700
N4—C251.292 (5)C18—H18B0.9600
N5—C261.288 (5)C18—H18A0.9600
N6—C281.466 (4)C18—H18C0.9600
N6—C301.385 (4)C19—H19C0.9600
N6—C221.400 (4)C19—H19B0.9600
N7—C311.338 (4)C19—H19A0.9600
N7—C291.430 (5)C20—C211.515 (5)
N8—N91.325 (5)C21—C241.496 (5)
N8—C331.320 (5)C21—C221.339 (5)
N8—C321.454 (5)C22—C231.524 (5)
N9—N101.279 (6)C26—C271.491 (6)
N10—N111.348 (7)C28—C291.548 (5)
N11—C331.307 (6)C29—C301.540 (5)
N7—H7N0.8600C31—C321.510 (5)
C1—C141.406 (5)C20—H20A0.9700
C1—C21.396 (5)C20—H20B0.9700
C1—C61.393 (5)C24—H24A0.9700
C2—C31.351 (7)C24—H24B0.9700
C3—C41.397 (7)C27—H27A0.9600
C4—C51.368 (6)C27—H27B0.9600
C5—C61.399 (5)C27—H27C0.9600
C7—C81.501 (5)C28—H280.9800
C8—C91.384 (6)C29—H290.9800
C8—C131.380 (5)C32—H32A0.9700
C9—C101.374 (6)C32—H32B0.9700
C10—C111.368 (6)C33—H330.9300
C20—S1—C2893.40 (17)C15—C16—H16B109.00
C24—S2—C25100.75 (17)C17—C16—H16B109.00
C25—S3—C2687.07 (17)H16A—C16—H16B108.00
C14—O1—C15118.3 (3)C17—C16—H16A109.00
N2—N1—C14103.8 (3)C16—C17—H17A109.00
C6—N2—C7127.5 (3)C16—C17—H17B109.00
N1—N2—C6111.9 (3)H17A—C17—H17B108.00
N1—N2—C7120.2 (3)N3—C17—H17B109.00
C17—N3—C18114.0 (4)N3—C17—H17A109.00
C17—N3—C19108.6 (3)N3—C18—H18B109.00
C18—N3—C19108.8 (4)N3—C18—H18A110.00
C17—N3—H3N108 (2)H18A—C18—H18C109.00
C18—N3—H3N111 (2)N3—C18—H18C109.00
C19—N3—H3N106 (2)H18A—C18—H18B109.00
N5—N4—C25112.2 (3)H18B—C18—H18C109.00
N4—N5—C26113.2 (3)N3—C19—H19B109.00
C22—N6—C30133.6 (3)N3—C19—H19C109.00
C22—N6—C28125.4 (3)H19A—C19—H19C109.00
C28—N6—C3094.1 (3)H19B—C19—H19C109.00
C29—N7—C31120.3 (3)H19A—C19—H19B109.00
N9—N8—C32120.7 (3)N3—C19—H19A109.00
C32—N8—C33131.6 (3)S1—C20—C21116.6 (3)
N9—N8—C33107.6 (3)C22—C21—C24122.5 (3)
N8—N9—N10107.5 (3)C20—C21—C22124.2 (3)
N9—N10—N11110.3 (4)C20—C21—C24113.3 (3)
N10—N11—C33105.2 (4)N6—C22—C23115.8 (3)
C29—N7—H7N120.00N6—C22—C21119.1 (3)
C31—N7—H7N120.00C21—C22—C23125.1 (3)
C6—C1—C14103.5 (3)O2—C23—C22117.7 (3)
C2—C1—C6120.5 (3)O2—C23—O3126.5 (3)
C2—C1—C14135.8 (4)O3—C23—C22115.8 (3)
C1—C2—C3118.5 (4)S2—C24—C21112.5 (2)
C2—C3—C4120.8 (4)S2—C25—N4126.6 (3)
C3—C4—C5122.3 (4)S2—C25—S3119.5 (2)
C4—C5—C6116.9 (4)S3—C25—N4114.0 (3)
N2—C6—C1107.0 (3)S3—C26—C27122.4 (3)
C1—C6—C5120.9 (3)S3—C26—N5113.6 (3)
N2—C6—C5132.1 (3)N5—C26—C27124.0 (4)
N2—C7—C8114.8 (3)N6—C28—C2987.8 (2)
C7—C8—C9121.4 (3)S1—C28—C29116.3 (2)
C7—C8—C13120.0 (3)S1—C28—N6109.8 (2)
C9—C8—C13118.6 (3)N7—C29—C28121.0 (3)
C8—C9—C10120.8 (4)N7—C29—C30119.8 (3)
C9—C10—C11119.9 (4)C28—C29—C3085.1 (3)
C10—C11—C12120.1 (4)O4—C30—N6132.0 (3)
C11—C12—C13120.4 (4)N6—C30—C2991.0 (3)
C8—C13—C12120.3 (3)O4—C30—C29137.0 (3)
N1—C14—C1113.8 (3)O5—C31—C32120.9 (3)
O1—C14—N1124.2 (3)O5—C31—N7123.9 (3)
O1—C14—C1122.1 (3)N7—C31—C32115.2 (3)
O1—C15—C16107.1 (4)N8—C32—C31110.4 (3)
C15—C16—C17114.2 (4)N8—C33—N11109.4 (4)
N3—C17—C16113.8 (4)S1—C20—H20A108.00
C1—C2—H2121.00S1—C20—H20B108.00
C3—C2—H2121.00C21—C20—H20A108.00
C4—C3—H3120.00C21—C20—H20B108.00
C2—C3—H3120.00H20A—C20—H20B107.00
C3—C4—H4119.00S2—C24—H24A109.00
C5—C4—H4119.00S2—C24—H24B109.00
C6—C5—H5122.00C21—C24—H24A109.00
C4—C5—H5122.00C21—C24—H24B109.00
N2—C7—H7A109.00H24A—C24—H24B108.00
C8—C7—H7B109.00C26—C27—H27A109.00
N2—C7—H7B109.00C26—C27—H27B109.00
C8—C7—H7A109.00C26—C27—H27C110.00
H7A—C7—H7B108.00H27A—C27—H27B109.00
C10—C9—H9120.00H27A—C27—H27C109.00
C8—C9—H9120.00H27B—C27—H27C109.00
C9—C10—H10120.00S1—C28—H28113.00
C11—C10—H10120.00N6—C28—H28113.00
C12—C11—H11120.00C29—C28—H28113.00
C10—C11—H11120.00N7—C29—H29110.00
C13—C12—H12120.00C28—C29—H29110.00
C11—C12—H12120.00C30—C29—H29110.00
C8—C13—H13120.00N8—C32—H32A110.00
C12—C13—H13120.00N8—C32—H32B110.00
O1—C15—H15B110.00C31—C32—H32A110.00
C16—C15—H15A110.00C31—C32—H32B110.00
O1—C15—H15A110.00H32A—C32—H32B108.00
H15A—C15—H15B109.00N8—C33—H33125.00
C16—C15—H15B110.00N11—C33—H33125.00
C15—C16—H16A109.00
C20—S1—C28—C29155.3 (3)N8—N9—N10—N110.1 (5)
C20—S1—C28—N657.8 (3)N9—N10—N11—C33−0.1 (5)
C28—S1—C20—C21−47.1 (3)N10—N11—C33—N80.2 (5)
C24—S2—C25—N412.6 (4)C2—C1—C6—N2−176.6 (3)
C24—S2—C25—S3−167.0 (2)C2—C1—C6—C52.6 (6)
C25—S2—C24—C21−111.3 (3)C14—C1—C2—C3−175.0 (4)
C25—S3—C26—C27−179.3 (3)C14—C1—C6—C5178.4 (3)
C26—S3—C25—N4−0.1 (3)C2—C1—C14—O1−5.2 (7)
C25—S3—C26—N5−0.4 (3)C14—C1—C6—N2−0.8 (4)
C26—S3—C25—S2179.6 (2)C6—C1—C2—C3−0.9 (6)
C14—O1—C15—C16−176.1 (3)C6—C1—C14—N1−0.5 (4)
C15—O1—C14—C1171.1 (3)C2—C1—C14—N1174.4 (4)
C15—O1—C14—N1−8.4 (5)C6—C1—C14—O1179.9 (3)
N2—N1—C14—C11.4 (4)C1—C2—C3—C4−1.7 (7)
C14—N1—N2—C7−175.3 (3)C2—C3—C4—C52.7 (7)
N2—N1—C14—O1−179.0 (3)C3—C4—C5—C6−1.0 (6)
C14—N1—N2—C6−1.9 (4)C4—C5—C6—C1−1.6 (6)
N1—N2—C6—C5−177.3 (4)C4—C5—C6—N2177.3 (4)
C7—N2—C6—C5−4.6 (7)N2—C7—C8—C948.2 (5)
N1—N2—C7—C8−102.2 (4)N2—C7—C8—C13−134.6 (4)
C6—N2—C7—C885.6 (5)C7—C8—C13—C12−176.7 (4)
C7—N2—C6—C1174.5 (3)C9—C8—C13—C120.6 (6)
N1—N2—C6—C11.7 (4)C13—C8—C9—C10−1.1 (6)
C19—N3—C17—C16−164.0 (4)C7—C8—C9—C10176.1 (4)
C18—N3—C17—C1674.5 (5)C8—C9—C10—C111.1 (6)
C25—N4—N5—C26−0.7 (4)C9—C10—C11—C12−0.5 (7)
N5—N4—C25—S30.4 (4)C10—C11—C12—C130.0 (7)
N5—N4—C25—S2−179.2 (3)C11—C12—C13—C80.0 (6)
N4—N5—C26—S30.6 (4)O1—C15—C16—C1759.5 (5)
N4—N5—C26—C27179.6 (3)C15—C16—C17—N3−173.0 (4)
C30—N6—C22—C21−133.6 (4)S1—C20—C21—C2219.2 (5)
C30—N6—C22—C2349.7 (5)S1—C20—C21—C24−163.3 (2)
C28—N6—C22—C23−167.3 (3)C20—C21—C22—N66.9 (5)
C30—N6—C28—C29−11.3 (3)C20—C21—C22—C23−176.7 (3)
C22—N6—C28—S1−48.2 (4)C20—C21—C24—S281.3 (3)
C22—N6—C28—C29−165.4 (3)C22—C21—C24—S2−101.2 (4)
C22—N6—C30—O4−16.5 (7)C24—C21—C22—N6−170.3 (3)
C28—N6—C22—C219.4 (5)C24—C21—C22—C236.0 (6)
C30—N6—C28—S1106.0 (2)N6—C22—C23—O232.8 (5)
C22—N6—C30—C29161.9 (4)C21—C22—C23—O337.0 (5)
C28—N6—C30—O4−167.1 (4)N6—C22—C23—O3−146.5 (3)
C28—N6—C30—C2911.3 (3)C21—C22—C23—O2−143.7 (4)
C29—N7—C31—O5−1.4 (5)S1—C28—C29—N721.1 (4)
C31—N7—C29—C30−145.3 (3)S1—C28—C29—C30−100.9 (3)
C29—N7—C31—C32176.6 (3)N6—C28—C29—N7132.1 (3)
C31—N7—C29—C28111.5 (4)N6—C28—C29—C3010.1 (2)
N9—N8—C32—C31−69.8 (4)N7—C29—C30—O444.4 (6)
N9—N8—C33—N11−0.1 (4)N7—C29—C30—N6−133.9 (3)
C32—N8—C33—N11−177.9 (3)C28—C29—C30—O4167.5 (5)
C33—N8—N9—N100.0 (4)C28—C29—C30—N6−10.7 (3)
C32—N8—N9—N10178.1 (4)O5—C31—C32—N8−38.1 (5)
C33—N8—C32—C31107.8 (4)N7—C31—C32—N8143.9 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3N···O3i0.96 (4)1.70 (4)2.660 (4)174 (3)
N7—H7N···O2ii0.86002.02002.868 (3)167.00
C18—H18C···O4iii0.96002.52003.303 (5)139.00
C24—H24A···N40.97002.41002.961 (5)116.00
C24—H24B···O30.97002.38002.882 (4)112.00
C32—H32A···O2iv0.97002.28003.218 (4)164.00
C32—H32B···O2ii0.97002.50003.318 (4)142.00
C19—H19B···CgA0.962.913.869 (6)174
C20—H20B···CgD0.972.723.642 (4)158
C29—H29···CgAii0.982.993.861 (4)149

Symmetry codes: (i) x, y−1, z+1; (ii) x, y−1, z; (iii) x, y, z+1; (iv) −x, y−1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5219).

References

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