Invariom modeling of ceftazidime pentahydrate: molecular properties from a 200 second synchrotron microcrystal experiment

Schürmann, C.J.; Pröpper, K.; Wagner, T.; Dittrich, B.

doi:10.1107/S0108768112017831

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Invariom modeling of ceftazidime pentahydrate: molecular properties from a 200 second synchrotron microcrystal experiment

C. J. Schürmann, K. Pröpper, T. Wagner and B. Dittrich

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.

Keywords: invariom modeling; synchrotron radiation; cephalosporin antibiotics.

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Supporting information

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

(I) top

Crystal data top

C₂₂H₂₂N₆O₇S₂·5(H₂O)	F(000) = 192.0
M_r = 636.68	D_x = 1.438 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Monochromated synchrotron radiation radiation, λ = 0.65000 Å
Hall symbol: P 2ac 2ab	Cell parameters from 12106 reflections
a = 8.9716 (5) Å	θ = 1.9–27.7°
b = 10.3943 (7) Å	µ = 0.20 mm⁻¹
c = 31.5444 (12) Å	T = 100 K
V = 2941.6 (3) Å³	Triangle, pale yellow
Z = 4.0	0.01 × 0.01 × 0.003 mm

Data collection top

Pilatus 6M diffractometer	8486 independent reflections
Radiation source: synchrotron	6506 reflections with F > 4(σ)F
Silicon 111 monochromator	R_int = 0.078
Detector resolution: 5.71 pixels mm^-1	θ_max = 27.7°, θ_min = 1.9°
ϕ scan	h = −12→12
Absorption correction: empirical (using intensity measurements) SADABS version 2008/2, multi-scan. (G. M. Sheldrick, 2008)	k = −13→13
T_min = 0.647, T_max = 0.746	l = −44→33
22933 measured reflections

Refinement top

Refinement on F	H-atom parameters constrained
Least-squares matrix: full	w1 = F_o*sqrt(w2) + sqrt(F_o²w2² + sqrt(w2²)) where w2 = q/[s²(F_o²) + (0.05 P)² + 0.00 P + 0.00 + 0.00 sin(th)] where P = (0.3333 F_o² + 0.6667 F_c²) q = 1.0
R[F² > 2σ(F²)] = 0.060	(Δ/σ)_max < 0.001
wR(F²) = 0.067	Δρ_max = 0.53 e Å⁻³
S = 1.52	Δρ_min = −0.57 e Å⁻³
6506 reflections	Absolute 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 parameters	Absolute structure parameter: 0.01 (11)
0 restraints

Crystal data top

C₂₂H₂₂N₆O₇S₂·5(H₂O)	V = 2941.6 (3) Å³
M_r = 636.68	Z = 4.0
Orthorhombic, P2₁2₁2₁	Monochromated synchrotron radiation radiation, λ = 0.65000 Å
a = 8.9716 (5) Å	µ = 0.20 mm⁻¹
b = 10.3943 (7) Å	T = 100 K
c = 31.5444 (12) Å	0.01 × 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
T_min = 0.647, T_max = 0.746	R_int = 0.078
22933 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	H-atom parameters constrained
wR(F²) = 0.067	Δρ_max = 0.53 e Å⁻³
S = 1.52	Δρ_min = −0.57 e Å⁻³
6506 reflections	Absolute 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 parameters	Absolute structure parameter: 0.01 (11)
0 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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)	0.9607	C(6)—H(6)	1.1010
O(7)—C(22)	1.211 (5)	C(8)—C(15)	1.507 (5)
O(1W)—H(11W)	0.9618	C(9)—H(9D)	1.0876
O(1W)—H(12W)	0.9618	C(9)—H(9E)	1.0876
O(2W)—H(21W)	0.9618	C(10)—C(11)	1.397 (5)
O(2W)—H(22W)	0.9618	C(10)—H(10)	1.0822
O(3W)—H(31W)	0.9618	C(11)—C(12)	1.393 (6)
O(3W)—H(32W)	0.9618	C(11)—H(11)	1.0822
O(4W)—H(41W)	0.9618	C(12)—C(13)	1.401 (5)
O(4W)—H(42W)	0.9618	C(12)—H(12)	1.0822
O(5W)—H(51W)	0.9618	C(13)—C(14)	1.376 (5)
O(5W)—H(52W)	0.9618	C(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)	1.0059	C(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)	1.0078	C(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 formula	C₂₂H₂₂N₆O₇S₂·5(H₂O)
M_r	636.68
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	8.9716 (5), 10.3943 (7), 31.5444 (12)
V (Å³)	2941.6 (3)
Z	4.0
Radiation type	Monochromated synchrotron, λ = 0.65000 Å
µ (mm⁻¹)	0.20
Crystal size (mm)	0.01 × 0.01 × 0.003

Data collection
Diffractometer	Pilatus 6M diffractometer
Absorption correction	Empirical (using intensity measurements) SADABS version 2008/2, multi-scan. (G. M. Sheldrick, 2008)
T_min, T_max	0.647, 0.746
No. of measured, independent and observed [F > 4(σ)F] reflections	22933, 8486, 6506
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.714

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.067, 1.52
No. of reflections	6506
No. of parameters	380
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.57
Absolute 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.
Absolute structure parameter	0.01 (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)	0.9607	C(6)—H(6)	1.1010
O(7)—C(22)	1.211 (5)	C(8)—C(15)	1.507 (5)
O(1W)—H(11W)	0.9618	C(9)—H(9D)	1.0876
O(1W)—H(12W)	0.9618	C(9)—H(9E)	1.0876
O(2W)—H(21W)	0.9618	C(10)—C(11)	1.397 (5)
O(2W)—H(22W)	0.9618	C(10)—H(10)	1.0822
O(3W)—H(31W)	0.9618	C(11)—C(12)	1.393 (6)
O(3W)—H(32W)	0.9618	C(11)—H(11)	1.0822
O(4W)—H(41W)	0.9618	C(12)—C(13)	1.401 (5)
O(4W)—H(42W)	0.9618	C(12)—H(12)	1.0822
O(5W)—H(51W)	0.9618	C(13)—C(14)	1.376 (5)
O(5W)—H(52W)	0.9618	C(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)	1.0059	C(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)	1.0078	C(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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