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The structure of ceftazidime pentahydrate, a third generation cephalosporin antibiotic, is reported. Data collection was carried out in a remarkably short time with synchrotron radiation and the latest detector technology, illustrating that single-crystal X-ray diffraction can be used as a technique for screening hundreds of compounds in a short amount of time. Structure refinement made use of invarioms, namely non-spherical scattering factors, which allow more information to be derived from a diffraction experiment. Properties that can be screened are bond-topological parameters, empirical hydrogen-bond energies, molecular dipole moments and electrostatic potentials.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768112017831/gw5017sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768112017831/gw5017Isup2.hkl
Contains datablock I

CCDC reference: 889426

Computing details top

Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: Koritsanszky et al., (2003); software used to prepare material for publication: enCIFer 1.3, CCDC, 2008.

Figures top
[Figure 1]
[Figure 2]
(I) top
Crystal data top
C22H22N6O7S2·5(H2O)F(000) = 192.0
Mr = 636.68Dx = 1.438 Mg m3
Orthorhombic, P212121Monochromated synchrotron radiation radiation, λ = 0.65000 Å
Hall symbol: P 2ac 2abCell parameters from 12106 reflections
a = 8.9716 (5) Åθ = 1.9–27.7°
b = 10.3943 (7) ŵ = 0.20 mm1
c = 31.5444 (12) ÅT = 100 K
V = 2941.6 (3) Å3Triangle, pale yellow
Z = 4.00.01 × 0.01 × 0.003 mm
Data collection top
Pilatus 6M
diffractometer
8486 independent reflections
Radiation source: synchrotron6506 reflections with F > 4(σ)F
Silicon 111 monochromatorRint = 0.078
Detector resolution: 5.71 pixels mm-1θmax = 27.7°, θmin = 1.9°
ϕ scanh = 1212
Absorption correction: empirical (using intensity measurements)
SADABS version 2008/2, multi-scan. (G. M. Sheldrick, 2008)
k = 1313
Tmin = 0.647, Tmax = 0.746l = 4433
22933 measured reflections
Refinement top
Refinement on FH-atom parameters constrained
Least-squares matrix: full w1 = Fo*sqrt(w2) + sqrt(Fo2w22 + sqrt(w22))
where w2 = q/[s2(Fo2) + (0.05 P)2 + 0.00 P + 0.00 + 0.00 sin(th)]
where P = (0.3333 Fo2 + 0.6667 Fc2) q = 1.0
R[F2 > 2σ(F2)] = 0.060(Δ/σ)max < 0.001
wR(F2) = 0.067Δρmax = 0.53 e Å3
S = 1.52Δρmin = 0.57 e Å3
6506 reflectionsAbsolute structure: An invariom refinement was performed (Dittrich, Acta Cryst. A62, 217) to improve the standard uncertainty of the Flack parameter (Flack, Acta Cryst, A39, 876) compared to an independent-atom refinement. After using non-spherical scattering factors the standard uncertainty is reduced and a reliable assignment (Flack, J. Appl. Cryst. (2000). 33, 1143) of absolute structure is possible.
380 parametersAbsolute structure parameter: 0.01 (11)
0 restraints
Crystal data top
C22H22N6O7S2·5(H2O)V = 2941.6 (3) Å3
Mr = 636.68Z = 4.0
Orthorhombic, P212121Monochromated synchrotron radiation radiation, λ = 0.65000 Å
a = 8.9716 (5) ŵ = 0.20 mm1
b = 10.3943 (7) ÅT = 100 K
c = 31.5444 (12) Å0.01 × 0.01 × 0.003 mm
Data collection top
Pilatus 6M
diffractometer
8486 independent reflections
Absorption correction: empirical (using intensity measurements)
SADABS version 2008/2, multi-scan. (G. M. Sheldrick, 2008)
6506 reflections with F > 4(σ)F
Tmin = 0.647, Tmax = 0.746Rint = 0.078
22933 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.060H-atom parameters constrained
wR(F2) = 0.067Δρmax = 0.53 e Å3
S = 1.52Δρmin = 0.57 e Å3
6506 reflectionsAbsolute structure: An invariom refinement was performed (Dittrich, Acta Cryst. A62, 217) to improve the standard uncertainty of the Flack parameter (Flack, Acta Cryst, A39, 876) compared to an independent-atom refinement. After using non-spherical scattering factors the standard uncertainty is reduced and a reliable assignment (Flack, J. Appl. Cryst. (2000). 33, 1143) of absolute structure is possible.
380 parametersAbsolute structure parameter: 0.01 (11)
0 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S(1)0.61410 (10)0.54170 (10)0.57640 (10)0.017
S(2)0.61570 (10)0.01860 (10)0.38410 (10)0.02
O(1)0.3678 (3)0.1877 (2)0.61790 (10)0.017
O(2)0.7347 (2)0.3170 (3)0.49940 (10)0.018
O(3)0.4634 (3)0.2683 (2)0.71370 (10)0.016
O(4)0.3050 (3)0.4342 (2)0.71250 (10)0.017
O(5)0.4296 (3)0.5057 (2)0.48000 (10)0.017
O(6)0.1162 (3)0.5455 (3)0.47440 (10)0.024
O(7)0.1793 (3)0.6016 (3)0.40870 (10)0.021
O(1W)0.8522 (3)0.5050 (3)0.44420 (10)0.023
O(2W)0.3613 (3)0.4714 (3)0.34710 (10)0.022
O(3W)0.3459 (3)0.6661 (2)0.27960 (10)0.02
O(4W)0.2531 (3)0.3137 (3)0.28410 (10)0.022
O(5W)0.4889 (3)0.3930 (3)0.22770 (10)0.025
N(1)0.5451 (3)0.3528 (3)0.63080 (10)0.012
N(2)0.5155 (3)0.2807 (3)0.53170 (10)0.013
N(3)0.4383 (3)0.7521 (3)0.69160 (10)0.013
N(4)0.4869 (3)0.2414 (3)0.38260 (10)0.013
N(5)0.4681 (4)0.1253 (3)0.31850 (10)0.022
N(6)0.4389 (3)0.4196 (3)0.44630 (10)0.015
C(1)0.4168 (4)0.3731 (3)0.69990 (10)0.013
C(2)0.5073 (3)0.4333 (3)0.66420 (10)0.011
C(3)0.5593 (4)0.5556 (3)0.66390 (10)0.013
C(4)0.6491 (4)0.6131 (4)0.62810 (10)0.018
C(5)0.6487 (3)0.3822 (3)0.59610 (10)0.014
C(6)0.5856 (3)0.2637 (3)0.57220 (10)0.013
C(7)0.4758 (3)0.2540 (3)0.60990 (10)0.011
C(8)0.5974 (3)0.3047 (3)0.49720 (10)0.013
C(9)0.5399 (4)0.6434 (3)0.70170 (10)0.014
C(10)0.2965 (4)0.7236 (4)0.68080 (10)0.018
C(11)0.1973 (4)0.8236 (4)0.67200 (10)0.022
C(12)0.2452 (4)0.9508 (4)0.67500 (10)0.025
C(13)0.3929 (4)0.9751 (4)0.68690 (10)0.023
C(14)0.4874 (4)0.8737 (3)0.69480 (10)0.018
C(15)0.5185 (3)0.3198 (3)0.45530 (10)0.011
C(16)0.5419 (4)0.2221 (3)0.42290 (10)0.013
C(17)0.6138 (4)0.1087 (3)0.43010 (10)0.017
C(18)0.5141 (4)0.1403 (3)0.35830 (10)0.015
C(19)0.3633 (4)0.6246 (3)0.46530 (10)0.016
C(20)0.3445 (4)0.7072 (4)0.50490 (10)0.023
C(21)0.4635 (4)0.6892 (4)0.43260 (10)0.023
C(22)0.2094 (4)0.5890 (3)0.44590 (10)0.016
H(6O)0.0199 (3)0.5324 (3)0.46180 (10)0.0357 (9)
H(2)0.4039 (3)0.2744 (3)0.52930 (10)0.0154 (7)
H(15N)0.4894 (4)0.0470 (3)0.30070 (10)0.0258 (8)
H(25N)0.4163 (4)0.1940 (3)0.30140 (10)0.0258 (8)
H(4A)0.7672 (4)0.6028 (4)0.63550 (10)0.0219 (9)
H(4B)0.6248 (4)0.7157 (4)0.62640 (10)0.0219 (9)
H(5)0.7645 (3)0.3688 (3)0.60540 (10)0.0168 (8)
H(6)0.6656 (3)0.1835 (3)0.57180 (10)0.0153 (8)
H(9D)0.4939 (4)0.5886 (3)0.72800 (10)0.0173 (8)
H(9E)0.6480 (4)0.6805 (3)0.71140 (10)0.0173 (8)
H(10)0.2598 (4)0.6246 (4)0.67900 (10)0.0211 (9)
H(11)0.0836 (4)0.8027 (4)0.66280 (10)0.0270 (10)
H(12)0.1696 (4)1.0293 (4)0.66820 (10)0.0300 (10)
H(13)0.4326 (4)1.0730 (4)0.68980 (10)0.0270 (9)
H(14)0.6019 (4)0.8920 (3)0.70380 (10)0.0217 (9)
H(17)0.6619 (4)0.0797 (3)0.45990 (10)0.0206 (8)
H(20A)0.2821 (4)0.6534 (4)0.52870 (10)0.0350 (10)
H(20B)0.2839 (4)0.7949 (4)0.49680 (10)0.0350 (10)
H(20C)0.4540 (4)0.7324 (4)0.51750 (10)0.0350 (10)
H(21A)0.5739 (4)0.7044 (4)0.44620 (10)0.0350 (10)
H(21B)0.4155 (4)0.7816 (4)0.42350 (10)0.0350 (10)
H(21C)0.4728 (4)0.6278 (4)0.40470 (10)0.0350 (10)
H(11W)0.8481 (3)0.4149 (3)0.45110 (10)0.0348 (9)
H(12W)0.7576 (3)0.5386 (3)0.45340 (10)0.0348 (9)
H(21W)0.4207 (3)0.4091 (3)0.36200 (10)0.0334 (9)
H(22W)0.3132 (3)0.5204 (3)0.36910 (10)0.0334 (9)
H(31W)0.3517 (3)0.7339 (2)0.30030 (10)0.0298 (9)
H(32W)0.3780 (3)0.5899 (2)0.29440 (10)0.0298 (9)
H(41W)0.2750 (3)0.3668 (3)0.30830 (10)0.0331 (9)
H(42W)0.1527 (3)0.2839 (3)0.28850 (10)0.0331 (9)
H(51W)0.4061 (3)0.3806 (3)0.24670 (10)0.0380 (10)
H(52W)0.5525 (3)0.3201 (3)0.23260 (10)0.0380 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S(1)0.0239 (4)0.0160 (4)0.0122 (4)0.0047 (4)0.0030 (4)0.0025 (3)
S(2)0.0285 (4)0.0143 (4)0.0160 (4)0.0070 (4)0.0013 (4)0.0023 (3)
O(1)0.0180 (10)0.0170 (10)0.0160 (10)0.0040 (10)0.0030 (10)0.0020 (10)
O(2)0.0060 (10)0.033 (2)0.0150 (10)0.0000 (10)0.0010 (10)0.0010 (10)
O(3)0.0190 (10)0.0140 (10)0.0150 (10)0.0020 (10)0.0040 (10)0.0030 (10)
O(4)0.0160 (10)0.0140 (10)0.0190 (10)0.0020 (10)0.0050 (10)0.0020 (10)
O(5)0.0200 (10)0.0130 (10)0.0180 (10)0.0030 (10)0.0020 (10)0.0020 (10)
O(6)0.0210 (10)0.0280 (10)0.0220 (10)0.0030 (10)0.0010 (10)0.0020 (10)
O(7)0.0180 (10)0.0250 (10)0.0210 (10)0.0010 (10)0.0010 (10)0.0040 (10)
O(1W)0.0200 (10)0.0200 (10)0.029 (2)0.0030 (10)0.0000 (10)0.0060 (10)
O(2W)0.0260 (10)0.0210 (10)0.0190 (10)0.0010 (10)0.0010 (10)0.0030 (10)
O(3W)0.0190 (10)0.0180 (10)0.023 (2)0.0040 (10)0.0030 (10)0.0010 (10)
O(4W)0.0200 (10)0.0260 (10)0.020 (2)0.0010 (10)0.0010 (10)0.0010 (10)
O(5W)0.0180 (10)0.0200 (10)0.038 (2)0.0010 (10)0.0060 (10)0.0070 (10)
N(1)0.0110 (10)0.0140 (10)0.0100 (10)0.0010 (10)0.0010 (10)0.0010 (10)
N(2)0.0080 (10)0.018 (2)0.0120 (10)0.0020 (10)0.0000 (10)0.0030 (10)
N(3)0.0160 (10)0.0100 (10)0.0140 (10)0.0000 (10)0.0030 (10)0.0020 (10)
N(4)0.0140 (10)0.0140 (10)0.0110 (10)0.0030 (10)0.0030 (10)0.0020 (10)
N(5)0.025 (2)0.025 (2)0.015 (2)0.0080 (10)0.0020 (10)0.0070 (10)
N(6)0.0140 (10)0.017 (2)0.012 (2)0.0040 (10)0.0020 (10)0.0020 (10)
C(1)0.017 (2)0.010 (2)0.012 (2)0.0000 (10)0.0020 (10)0.0010 (10)
C(2)0.0120 (10)0.011 (2)0.012 (2)0.0020 (10)0.0020 (10)0.0010 (10)
C(3)0.0180 (10)0.006 (2)0.014 (2)0.0030 (10)0.0020 (10)0.0020 (10)
C(4)0.024 (2)0.017 (2)0.013 (2)0.0080 (10)0.0060 (10)0.0020 (10)
C(5)0.0070 (10)0.022 (2)0.013 (2)0.0010 (10)0.0010 (10)0.0010 (10)
C(6)0.0110 (10)0.015 (2)0.012 (2)0.0020 (10)0.0030 (10)0.0020 (10)
C(7)0.0110 (10)0.012 (2)0.010 (2)0.0000 (10)0.0020 (10)0.0010 (10)
C(8)0.0100 (10)0.015 (2)0.013 (2)0.0020 (10)0.0010 (10)0.0020 (10)
C(9)0.015 (2)0.012 (2)0.016 (2)0.0010 (10)0.0030 (10)0.0000 (10)
C(10)0.012 (2)0.014 (2)0.027 (2)0.0000 (10)0.0040 (10)0.0020 (10)
C(11)0.016 (2)0.020 (2)0.031 (2)0.0020 (10)0.005 (2)0.002 (2)
C(12)0.024 (2)0.016 (2)0.036 (2)0.0050 (10)0.005 (2)0.004 (2)
C(13)0.025 (2)0.013 (2)0.030 (2)0.002 (2)0.007 (2)0.004 (2)
C(14)0.022 (2)0.010 (2)0.022 (2)0.0020 (10)0.006 (2)0.0030 (10)
C(15)0.0120 (10)0.010 (2)0.012 (2)0.0050 (10)0.0010 (10)0.0010 (10)
C(16)0.0150 (10)0.013 (2)0.011 (2)0.0030 (10)0.0000 (10)0.0020 (10)
C(17)0.025 (2)0.012 (2)0.014 (2)0.0080 (10)0.002 (2)0.0000 (10)
C(18)0.0140 (10)0.015 (2)0.015 (2)0.0040 (10)0.0010 (10)0.0040 (10)
C(19)0.017 (2)0.012 (2)0.018 (2)0.0040 (10)0.0030 (10)0.0030 (10)
C(20)0.024 (2)0.021 (2)0.026 (2)0.0060 (10)0.004 (2)0.010 (2)
C(21)0.021 (2)0.021 (2)0.028 (2)0.0040 (10)0.003 (2)0.001 (2)
C(22)0.019 (2)0.014 (2)0.015 (2)0.0020 (10)0.0010 (10)0.0010 (10)
Geometric parameters (Å, º) top
S(1)—C(5)1.797 (4)N(6)—C(15)1.291 (4)
S(2)—C(17)1.726 (4)C(1)—C(2)1.523 (5)
S(2)—C(18)1.760 (4)C(2)—C(3)1.353 (4)
O(1)—C(7)1.216 (4)C(3)—C(4)1.512 (5)
O(2)—C(8)1.240 (4)C(3)—C(9)1.511 (5)
O(3)—C(1)1.246 (4)C(4)—H(4A)1.0893
O(4)—C(1)1.252 (4)C(4)—H(4B)1.0893
O(6)—C(22)1.309 (4)C(5)—H(5)1.0887
O(6)—H(6O)0.9607C(6)—H(6)1.1010
O(7)—C(22)1.211 (5)C(8)—C(15)1.507 (5)
O(1W)—H(11W)0.9618C(9)—H(9D)1.0876
O(1W)—H(12W)0.9618C(9)—H(9E)1.0876
O(2W)—H(21W)0.9618C(10)—C(11)1.397 (5)
O(2W)—H(22W)0.9618C(10)—H(10)1.0822
O(3W)—H(31W)0.9618C(11)—C(12)1.393 (6)
O(3W)—H(32W)0.9618C(11)—H(11)1.0822
O(4W)—H(41W)0.9618C(12)—C(13)1.401 (5)
O(4W)—H(42W)0.9618C(12)—H(12)1.0822
O(5W)—H(51W)0.9618C(13)—C(14)1.376 (5)
O(5W)—H(52W)0.9618C(13)—H(13)1.0822
N(1)—C(2)1.388 (4)C(14)—H(14)1.0822
N(1)—C(5)1.468 (4)C(15)—C(16)1.457 (5)
N(1)—C(7)1.369 (4)C(16)—C(17)1.362 (5)
N(2)—C(6)1.433 (4)C(17)—H(17)1.0762
N(2)—C(8)1.337 (4)C(19)—C(20)1.524 (5)
N(2)—H(2)1.0059C(19)—C(21)1.523 (5)
N(3)—C(10)1.349 (4)C(20)—H(20A)1.0914
N(3)—C(14)1.342 (4)C(20)—H(20B)1.0914
N(4)—C(16)1.378 (5)C(20)—H(20C)1.0914
N(4)—C(18)1.323 (4)C(21)—H(21A)1.0914
N(5)—C(18)1.332 (5)C(21)—H(21B)1.0914
N(5)—H(15N)1.0078C(21)—H(21C)1.0914
N(5)—H(25N)1.0078
C(17)—S(2)—C(18)89.61 (17)O(2)—C(8)—C(15)120.2 (3)
C(22)—O(6)—H(6O)109.8 (2)N(2)—C(8)—C(15)118.3 (3)
C(2)—N(1)—C(5)126.5 (3)N(3)—C(10)—C(11)119.2 (3)
C(2)—N(1)—C(7)135.0 (3)C(10)—C(11)—C(12)119.7 (3)
C(5)—N(1)—C(7)94.9 (3)C(11)—C(12)—C(13)118.8 (4)
C(6)—N(2)—C(8)120.4 (3)C(12)—C(13)—C(14)119.6 (4)
C(10)—N(3)—C(14)122.4 (3)N(3)—C(14)—C(13)120.4 (3)
C(16)—N(4)—C(18)110.6 (3)N(6)—C(15)—C(8)122.5 (3)
O(3)—C(1)—O(4)127.0 (3)N(6)—C(15)—C(16)119.0 (3)
O(3)—C(1)—C(2)116.1 (3)C(8)—C(15)—C(16)118.4 (3)
O(4)—C(1)—C(2)116.9 (3)N(4)—C(16)—C(15)119.6 (3)
N(1)—C(2)—C(1)116.3 (3)N(4)—C(16)—C(17)116.7 (3)
N(1)—C(2)—C(3)118.5 (3)C(15)—C(16)—C(17)123.6 (3)
C(1)—C(2)—C(3)125.1 (3)S(2)—C(17)—C(16)109.5 (3)
C(2)—C(3)—C(4)124.1 (3)S(2)—C(18)—N(4)113.5 (3)
C(2)—C(3)—C(9)121.5 (3)S(2)—C(18)—N(5)120.9 (3)
C(4)—C(3)—C(9)114.3 (3)N(4)—C(18)—N(5)125.6 (3)
S(1)—C(5)—N(1)109.9 (2)C(20)—C(19)—C(21)111.8 (3)
O(1)—C(7)—N(1)133.4 (3)O(6)—C(22)—O(7)124.1 (3)
O(2)—C(8)—N(2)121.4 (3)

Experimental details

Crystal data
Chemical formulaC22H22N6O7S2·5(H2O)
Mr636.68
Crystal system, space groupOrthorhombic, P212121
Temperature (K)100
a, b, c (Å)8.9716 (5), 10.3943 (7), 31.5444 (12)
V3)2941.6 (3)
Z4.0
Radiation typeMonochromated synchrotron, λ = 0.65000 Å
µ (mm1)0.20
Crystal size (mm)0.01 × 0.01 × 0.003
Data collection
DiffractometerPilatus 6M
diffractometer
Absorption correctionEmpirical (using intensity measurements)
SADABS version 2008/2, multi-scan. (G. M. Sheldrick, 2008)
Tmin, Tmax0.647, 0.746
No. of measured, independent and
observed [F > 4(σ)F] reflections
22933, 8486, 6506
Rint0.078
(sin θ/λ)max1)0.714
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.067, 1.52
No. of reflections6506
No. of parameters380
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.53, 0.57
Absolute structureAn invariom refinement was performed (Dittrich, Acta Cryst. A62, 217) to improve the standard uncertainty of the Flack parameter (Flack, Acta Cryst, A39, 876) compared to an independent-atom refinement. After using non-spherical scattering factors the standard uncertainty is reduced and a reliable assignment (Flack, J. Appl. Cryst. (2000). 33, 1143) of absolute structure is possible.
Absolute structure parameter0.01 (11)

Computer programs: SHELXS97 (Sheldrick, 2008), Koritsanszky et al., (2003), enCIFer 1.3, CCDC, 2008.

Selected geometric parameters (Å, º) top
S(1)—C(5)1.797 (4)N(6)—C(15)1.291 (4)
S(2)—C(17)1.726 (4)C(1)—C(2)1.523 (5)
S(2)—C(18)1.760 (4)C(2)—C(3)1.353 (4)
O(1)—C(7)1.216 (4)C(3)—C(4)1.512 (5)
O(2)—C(8)1.240 (4)C(3)—C(9)1.511 (5)
O(3)—C(1)1.246 (4)C(4)—H(4A)1.0893
O(4)—C(1)1.252 (4)C(4)—H(4B)1.0893
O(6)—C(22)1.309 (4)C(5)—H(5)1.0887
O(6)—H(6O)0.9607C(6)—H(6)1.1010
O(7)—C(22)1.211 (5)C(8)—C(15)1.507 (5)
O(1W)—H(11W)0.9618C(9)—H(9D)1.0876
O(1W)—H(12W)0.9618C(9)—H(9E)1.0876
O(2W)—H(21W)0.9618C(10)—C(11)1.397 (5)
O(2W)—H(22W)0.9618C(10)—H(10)1.0822
O(3W)—H(31W)0.9618C(11)—C(12)1.393 (6)
O(3W)—H(32W)0.9618C(11)—H(11)1.0822
O(4W)—H(41W)0.9618C(12)—C(13)1.401 (5)
O(4W)—H(42W)0.9618C(12)—H(12)1.0822
O(5W)—H(51W)0.9618C(13)—C(14)1.376 (5)
O(5W)—H(52W)0.9618C(13)—H(13)1.0822
N(1)—C(2)1.388 (4)C(14)—H(14)1.0822
N(1)—C(5)1.468 (4)C(15)—C(16)1.457 (5)
N(1)—C(7)1.369 (4)C(16)—C(17)1.362 (5)
N(2)—C(6)1.433 (4)C(17)—H(17)1.0762
N(2)—C(8)1.337 (4)C(19)—C(20)1.524 (5)
N(2)—H(2)1.0059C(19)—C(21)1.523 (5)
N(3)—C(10)1.349 (4)C(20)—H(20A)1.0914
N(3)—C(14)1.342 (4)C(20)—H(20B)1.0914
N(4)—C(16)1.378 (5)C(20)—H(20C)1.0914
N(4)—C(18)1.323 (4)C(21)—H(21A)1.0914
N(5)—C(18)1.332 (5)C(21)—H(21B)1.0914
N(5)—H(15N)1.0078C(21)—H(21C)1.0914
N(5)—H(25N)1.0078
C(17)—S(2)—C(18)89.61 (17)O(2)—C(8)—C(15)120.2 (3)
C(22)—O(6)—H(6O)109.8 (2)N(2)—C(8)—C(15)118.3 (3)
C(2)—N(1)—C(5)126.5 (3)N(3)—C(10)—C(11)119.2 (3)
C(2)—N(1)—C(7)135.0 (3)C(10)—C(11)—C(12)119.7 (3)
C(5)—N(1)—C(7)94.9 (3)C(11)—C(12)—C(13)118.8 (4)
C(6)—N(2)—C(8)120.4 (3)C(12)—C(13)—C(14)119.6 (4)
C(10)—N(3)—C(14)122.4 (3)N(3)—C(14)—C(13)120.4 (3)
C(16)—N(4)—C(18)110.6 (3)N(6)—C(15)—C(8)122.5 (3)
O(3)—C(1)—O(4)127.0 (3)N(6)—C(15)—C(16)119.0 (3)
O(3)—C(1)—C(2)116.1 (3)C(8)—C(15)—C(16)118.4 (3)
O(4)—C(1)—C(2)116.9 (3)N(4)—C(16)—C(15)119.6 (3)
N(1)—C(2)—C(1)116.3 (3)N(4)—C(16)—C(17)116.7 (3)
N(1)—C(2)—C(3)118.5 (3)C(15)—C(16)—C(17)123.6 (3)
C(1)—C(2)—C(3)125.1 (3)S(2)—C(17)—C(16)109.5 (3)
C(2)—C(3)—C(4)124.1 (3)S(2)—C(18)—N(4)113.5 (3)
C(2)—C(3)—C(9)121.5 (3)S(2)—C(18)—N(5)120.9 (3)
C(4)—C(3)—C(9)114.3 (3)N(4)—C(18)—N(5)125.6 (3)
S(1)—C(5)—N(1)109.9 (2)C(20)—C(19)—C(21)111.8 (3)
O(1)—C(7)—N(1)133.4 (3)O(6)—C(22)—O(7)124.1 (3)
O(2)—C(8)—N(2)121.4 (3)
 

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