On the transfer of theoretical multipole parameters for restoring static electron density and revealing and treating atomic anharmonic motion. Features of chemical bonding in crystals of an isocyanuric acid derivative

The crystal and electronic structure of an isocyanuric acid derivative was studied by high-resolution single-crystal X-ray diffraction within the Hansen–Coppens multipole formalism. The observed deformation electron density shows signs of thermal smearing. The experimental picture meaningfully assigned to the consequences of unmodelled anharmonic atomic motion. Straightforward simultaneous refinement of all parameters, including Gram–Charlier coefficients, resulted in more significant distortion of apparent static electron density, even though the residual density became significantly flatter and more featureless. Further, the method of transferring multipole parameters from the model refined against theoretical structure factors as an initial guess was employed, followed by the subsequent block refinement of Gram–Charlier coefficients and the other parameters. This procedure allowed us to appropriately distinguish static electron density from the contaminant smearing effects of insufficiently accounted atomic motion. In particular, some covalent bonds and the weak π...π interaction between isocyanurate moieties were studied via the mutual penetration of atomic-like kinetic and electrostatic potential φ-basins with complementary atomic ρ-basins. Further, local electronic temperature was applied as an advanced descriptor for both covalent bonds and noncovalent interactions. Total probability density function (PDF) of nuclear displacement showed virtually no negative regions close to and around the atomic nuclei. The distribution of anharmonic PDF to a certain extent matched the residual electron density from the multipole model before anharmonic refinement. No signs of disordering of the sulfonyl group hidden in the modelled anharmonic motion were found in the PDF.

Computing details

Data collection: APEX3 v2019.11-0 (Bruker AXS); cell refinement: APEX3 v2019.11-0 (Bruker AXS); data reduction: APEX3 v2019.11-0 (Bruker AXS); program(s) used to solve structure: SHELXT-2018/2 (Sheldrick, 2015); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015) for Independent Atom Model refinement; MoPro [version of June 2021] (Jelsch, Guillot et al., 2005) for refinement within the Hansen-Coppens multipole formalism; molecular graphics: MoProViewer v.1.2000 (Jelsch, Guillot et al., 2005); 3DPlot v.2.5.25 (Stash & Tsirelson, 2014); TrajPlot v1.4.0.2 (Stash & Tsirelson, 2014); WinGX v.2021.3 & ORTEP-3 v.2014.1 (Farrugia, 2012); Mercury 2020.3.0 (Macrae, 2020); software used to prepare material for publication: WinXPRO v.3.4.41 (Stash & Tsirelson, 2014); VMoPro [version of June 2021] (Jelsch, Guillot et al., 2005); PLATON [version of June 14th, 2021] (Spek, 2009).

1-{2-[2-(methoxycarbonylmethylsulfonyl)ethoxy]ethyl}-3,5-dimethylisocyanurate

Crystal data

C12H19N3O8S	Dx = 1.544 Mg m^−3
Mr = 365.36	Melting point: 393 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.2921 (5) Å	Cell parameters from 9891 reflections
b = 17.8132 (8) Å	θ = 2.2–48.0°
c = 8.3448 (4) Å	µ = 0.26 mm^−1
β = 110.575 (2)°	T = 100 K
V = 1571.47 (13) Å^3	Prism, colorless
Z = 4	0.31 × 0.30 × 0.22 mm
F(000) = 768

Data collection

Bruker KAPPA APEX II diffractometer	19390 independent reflections
Radiation source: sealed x-ray tube, Siemens sealed x-ray tube	12487 reflections with I > 3σ(I)
Graphite monochromator	Rint = 0.030
ω and φ scans	θmax = 55.0°, θmin = 1.9°
Absorption correction: numerical SADABS-2016/2 (Stalke et al., 2015) Equivalent reflections defined by point group 2/m for scaling and error model Restraint esd for equal adjacent scale factors = 0.0050 Maximum odd and even orders for spherical harmonics = 1 4 130667 reflections employed for parameter determination Effective data to parameter ratio = 14.14 wR2(int) = 0.0477 (selected reflections only, before parameter refinement) wR2(int) = 0.0436 (selected reflections only, after parameter refinement) Run 2theta R(int) Incid. factors Diffr. factors K g I/s(lim) Total I>2sig(I) 1 -7.5 0.0220 0.593 - 0.630 0.991 - 1.011 0.797 0.0176 56.7 6018 5350 2 7.5 0.0223 0.593 - 0.614 0.989 - 1.011 0.701 0.0176 56.7 3195 2781 3 47.5 0.0317 0.604 - 0.636 0.985 - 1.011 0.641 0.0176 56.7 20772 16058 4 -10.0 0.0216 0.591 - 0.611 0.991 - 1.011 0.683 0.0176 56.7 1674 1468 5 35.0 0.0293 0.584 - 0.611 0.985 - 1.011 0.663 0.0176 56.7 15219 12134 6 42.5 0.0443 0.564 - 0.627 0.991 - 1.011 0.684 0.0176 56.7 12933 9246 7 35.0 0.0239 0.578 - 0.618 0.994 - 1.011 0.675 0.0176 56.7 8562 7170 8 27.5 0.0240 0.587 - 0.661 0.985 - 1.011 0.663 0.0176 56.7 12387 10378 9 -27.5 0.0243 0.586 - 0.619 0.988 - 1.011 0.713 0.0176 56.7 10333 8724 10 -10.0 0.0256 0.604 - 0.632 0.991 - 1.011 0.687 0.0176 56.7 2582 2251 11 -52.5 0.0336 0.608 - 0.635 0.987 - 1.011 0.639 0.0176 56.7 3692 2871 12 -65.0 0.0483 0.595 - 0.631 0.996 - 1.011 0.752 0.0176 56.7 3126 2116 13 -85.0 0.0855 0.646 - 0.676 0.986 - 1.011 0.660 0.0176 56.7 10184 5134 14 -57.5 0.0345 0.635 - 0.729 0.991 - 1.011 0.731 0.0176 56.7 4790 3555 15 -75.0 0.0565 0.606 - 0.642 0.985 - 1.011 0.619 0.0176 56.7 27040 17030 16 60.0 0.0320 0.611 - 0.657 0.983 - 1.010 0.634 0.0176 56.7 20189 15304 17 75.0 0.0536 0.597 - 0.674 0.984 - 1.010 0.609 0.0176 56.7 20715 13600 18 40.0 0.0356 0.578 - 0.588 1.002 - 1.011 0.671 0.0176 56.7 211 160 19 40.0 0.0430 0.596 - 0.606 0.998 - 1.011 0.659 0.0176 56.7 222 150 20 40.0 0.0458 0.597 - 0.612 1.000 - 1.008 0.794 0.0176 56.7 235 162 Estimated minimum and maximum transmission: 0.8763 0.9074 Additional spherical absorption correction applied with mu*r = 0.0440 Lambda/2 correction factor = 0.00150	h = −25→25
Tmin = 0.876, Tmax = 0.907	k = −41→38
180475 measured reflections	l = −17→18

Refinement

Refinement on F	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.021	Only H-atom coordinates refined
S = 1.39	Weighting scheme based on measured s.u.'s weight w was equal to 1/σ^2(F^1)
12487 reflections	(Δ/σ)max = 0.001
150 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3
Primary atom site location: structure-invariant direct methods

Special details

Refinement. The refinement was performed against F¹ with the reflections that satisfy the I > 3σ(I) condition. One scale factor was refined. Electroneutrality constraint was imposed on the whole asymmetric cell. The C-H adistances were constrained to the calculated values obtained from the optimized crystal structure. The anisotropic displacement parameters for H-atoms were estimated using the SHADE3 algorithm (Madsen, 2006). Multipole expansion was truncated at the hexadecapole level for the sulfur atom, the octupole level for the other non-hydrogen atoms, and the dipole level for the hydrogen atoms; only the bond- oriented dipoles P10 for all H-atoms were refined. Local symmetry constraints were introduced on multipole parameters. The single κ' parameter was used for all multipoles of each atom. The transfer of multipole parameters from the model refined against theoretical structure factors into the experimental model was performed to reveal the parameters describing the atomic anharmonic motion. A block refinement of the Gram-Charlier coefficients identified by the above- mentioned method and the other parameters led to the final model. No negative values of total electron density were observed. All covalent bonds with non- hydrogen atoms satisfied the rigid bond criterion. Among the all anharmonically refined atoms, no noticeable negative regions of total probability density function of nuclear displacement were observed. More detailed description is in the article.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.464163 (6)	0.622306 (1)	0.361670 (9)	0.013773 (6)
O2	0.75455 (2)	0.45539 (3)	1.17134 (5)	0.02282 (3)
O4	0.89848 (2)	0.34089 (3)	0.78950 (7)	0.02430 (3)
O6	0.86540 (2)	0.59448 (2)	0.79017 (5)	0.01779 (2)
O9	0.58115 (4)	0.623997 (13)	0.77436 (6)	0.01545 (3)
O1	0.39821 (2)	0.551928 (19)	0.33923 (3)	0.01678 (3)
O3	0.439384 (19)	0.669640 (17)	0.21485 (5)	0.01889 (2)
O5	0.69410 (4)	0.72814 (3)	0.52276 (3)	0.01834 (4)
O14	0.81018 (4)	0.65393 (2)	0.41734 (3)	0.01499 (3)
N1	0.80194 (2)	0.52647 (2)	0.97591 (4)	0.01294 (2)
N3	0.83695 (2)	0.39639 (2)	0.99264 (5)	0.01499 (2)
N5	0.88746 (2)	0.46785 (2)	0.79006 (4)	0.01369 (2)
C2	0.79436 (2)	0.458983 (17)	1.05393 (4)	0.01437 (2)
C4	0.87472 (2)	0.397568 (17)	0.85258 (4)	0.01503 (2)
C6	0.852002 (19)	0.534012 (16)	0.84777 (3)	0.012197 (19)
C3	0.83493 (2)	0.324510 (19)	1.07591 (4)	0.02198 (3)
C5	0.92552 (2)	0.470938 (16)	0.63973 (4)	0.01954 (2)
C7	0.75037 (3)	0.593259 (17)	1.03173 (4)	0.01634 (2)
C8	0.60829 (3)	0.599906 (15)	0.94538 (5)	0.01684 (3)
C10	0.45003 (3)	0.633613 (16)	0.68675 (5)	0.01820 (3)
C11	0.43048 (2)	0.674940 (17)	0.52055 (5)	0.01678 (3)
C12	0.62829 (3)	0.600377 (16)	0.44227 (3)	0.01304 (2)
C13	0.71218 (2)	0.668739 (16)	0.46629 (3)	0.01269 (2)
C15	0.89649 (3)	0.715481 (17)	0.43315 (4)	0.01992 (3)
H3A	0.751 (14)	0.3234 (2)	1.1112 (4)	0.04217
H3B	0.8312 (3)	0.281 (14)	0.9831 (4)	0.04309
H3C	0.921 (14)	0.3192 (2)	1.1891 (3)	0.04416
H5A	1.014 (14)	0.44033 (17)	0.6672 (5)	0.04121
H5B	0.8516 (3)	0.446 (14)	0.5298 (3)	0.03718
H5C	0.9380 (3)	0.530 (14)	0.6165 (5)	0.03630
H7A	0.7745 (4)	0.5885 (3)	1.169 (14)	0.03491
H7B	0.7971 (4)	0.642 (14)	1.0025 (6)	0.03160
H8A	0.5623 (4)	0.546 (14)	0.9483 (6)	0.03186
H8B	0.5748 (4)	0.643 (14)	1.0151 (5)	0.03553
H10A	0.4015 (4)	0.579 (14)	0.6621 (6)	0.03237
H10B	0.4093 (4)	0.669 (14)	0.7622 (5)	0.03562
H11A	0.4866 (4)	0.726 (14)	0.5426 (6)	0.03119
H11B	0.330 (14)	0.6883 (3)	0.4549 (6)	0.03500
H12A	0.6461 (4)	0.573 (14)	0.5650 (3)	0.02598
H12B	0.6408 (4)	0.561 (14)	0.3499 (4)	0.02838
H15A	0.8442 (2)	0.761 (14)	0.3517 (3)	0.04009
H15B	0.9337 (3)	0.73281 (16)	0.567 (14)	0.03949
H15C	0.972 (14)	0.69556 (15)	0.3914 (4)	0.04270

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01274 (2)	0.01191 (2)	0.01476 (3)	−0.001057 (18)	0.002454 (18)	0.00056 (2)
O2	0.02926 (15)	0.02448 (16)	0.01968 (11)	−0.00214 (9)	0.01478 (13)	0.00314 (12)
O4	0.02772 (16)	0.01751 (14)	0.03040 (15)	0.00492 (7)	0.01361 (14)	−0.00140 (12)
O6	0.02058 (11)	0.01630 (12)	0.01803 (10)	−0.00222 (7)	0.00870 (12)	0.00233 (9)
O9	0.01556 (13)	0.01778 (13)	0.01537 (15)	0.00045 (7)	0.00836 (12)	−0.00002 (10)
O1	0.01398 (8)	0.01424 (8)	0.01887 (14)	−0.00266 (7)	0.00171 (9)	−0.00043 (8)
O3	0.01849 (9)	0.01783 (9)	0.01733 (10)	−0.00011 (10)	0.00253 (9)	0.00410 (9)
O5	0.01890 (11)	0.01178 (11)	0.02771 (18)	−0.00262 (10)	0.01239 (12)	−0.00505 (10)
O14	0.01612 (10)	0.01482 (11)	0.01645 (14)	−0.00337 (8)	0.00876 (10)	−0.00350 (9)
N1	0.01459 (10)	0.01377 (10)	0.01116 (9)	−0.00143 (6)	0.00540 (9)	−0.00040 (9)
N3	0.01338 (10)	0.01455 (10)	0.01706 (11)	0.00127 (7)	0.00537 (10)	0.00404 (10)
N5	0.01259 (10)	0.01555 (12)	0.01409 (10)	0.00086 (7)	0.00614 (9)	0.00076 (10)
C2	0.01470 (9)	0.01605 (10)	0.01289 (10)	−0.00132 (7)	0.00548 (8)	0.00190 (9)
C4	0.01301 (9)	0.01453 (9)	0.01761 (11)	0.00180 (7)	0.00545 (8)	0.00092 (9)
C6	0.01110 (8)	0.01411 (9)	0.01118 (9)	−0.00127 (6)	0.00366 (7)	0.00046 (8)
C3	0.02112 (11)	0.01771 (10)	0.02680 (14)	0.00213 (8)	0.00802 (10)	0.00901 (10)
C5	0.02095 (10)	0.02370 (12)	0.01746 (11)	0.00284 (8)	0.01111 (9)	0.00071 (10)
C7	0.02080 (12)	0.01563 (9)	0.01358 (11)	−0.00201 (8)	0.00728 (9)	−0.00353 (10)
C8	0.02054 (12)	0.01681 (11)	0.01712 (13)	0.00113 (8)	0.01156 (10)	0.00001 (9)
C10	0.01548 (11)	0.02102 (12)	0.02083 (13)	−0.00059 (8)	0.00977 (10)	−0.00055 (11)
C11	0.01462 (10)	0.01475 (10)	0.02107 (14)	0.00193 (8)	0.00639 (8)	0.00000 (11)
C12	0.01312 (9)	0.01095 (9)	0.01489 (12)	−0.00125 (8)	0.00470 (7)	−0.00070 (8)
C13	0.01345 (8)	0.01142 (9)	0.01367 (11)	−0.00169 (7)	0.00534 (8)	−0.00141 (8)
C15	0.01890 (10)	0.01871 (10)	0.02556 (14)	−0.00590 (8)	0.01207 (9)	−0.00406 (10)
H3A	0.03698	0.04128	0.05557	0.00421	0.02538	0.01542
H3B	0.06103	0.02809	0.04169	0.00265	0.01998	0.00100
H3C	0.03587	0.04542	0.03977	0.00092	−0.00095	0.01536
H5A	0.03228	0.05100	0.04558	0.02042	0.02019	0.01029
H5B	0.03574	0.04586	0.02995	−0.00693	0.01154	−0.00900
H5C	0.04897	0.02497	0.04305	−0.00106	0.02627	0.00234
H7A	0.04369	0.04314	0.01878	0.00263	0.01207	−0.00066
H7B	0.03574	0.02596	0.03557	−0.00628	0.01562	−0.00100
H8A	0.03312	0.02826	0.03602	−0.00452	0.01443	0.00397
H8B	0.04465	0.03555	0.03254	0.00890	0.02124	−0.00565
H10A	0.02863	0.02665	0.04089	−0.00441	0.01105	0.00361
H10B	0.03803	0.03714	0.03917	0.01208	0.02290	−0.00004
H11A	0.03637	0.02321	0.03709	−0.00584	0.01679	−0.00314
H11B	0.02199	0.04146	0.04046	0.00803	0.00962	0.00606
H12A	0.02689	0.02932	0.02135	−0.00239	0.00800	0.00440
H12B	0.03250	0.02706	0.02722	−0.00193	0.01256	−0.01089
H15A	0.03771	0.03215	0.04666	−0.00210	0.01015	0.01352
H15B	0.04462	0.04384	0.02944	−0.01773	0.01230	−0.00437
H15C	0.03661	0.04445	0.05933	−0.00304	0.03217	−0.00088

Geometric parameters (Å, º)

S1—O3	1.4316 (4)	C3—H3A	1.0872
S1—O1	1.4364 (4)	C3—H3C	1.0924
S1—C11	1.7709 (4)	C5—H5C	1.0877
S1—C12	1.7787 (3)	C5—H5A	1.0906
O2—C2	1.2147 (6)	C5—H5B	1.0934
O4—C4	1.2114 (6)	C7—C8	1.5148 (5)
O6—C6	1.2105 (5)	C7—H7A	1.0870
O9—C10	1.4125 (5)	C7—H7B	1.0871
O9—C8	1.4168 (6)	C8—H8A	1.0989
O5—C13	1.2046 (5)	C8—H8B	1.1010
O14—C13	1.3337 (5)	C10—C11	1.5162 (5)
O14—C15	1.4419 (5)	C10—H10A	1.0986
N1—C6	1.3805 (5)	C10—H10B	1.0993
N1—C2	1.3841 (5)	C11—H11A	1.0903
N1—C7	1.4705 (5)	C11—H11B	1.0953
N3—C4	1.3779 (5)	C12—C13	1.5123 (4)
N3—C2	1.3816 (5)	C12—H12A	1.0916
N3—C3	1.4609 (5)	C12—H12B	1.0932
N5—C4	1.3830 (5)	C15—H15C	1.0901
N5—C6	1.3846 (5)	C15—H15A	1.0919
N5—C5	1.4630 (5)	C15—H15B	1.0923
C3—H3B	1.0868
O3—S1—O1	117.777 (15)	N1—C7—H7A	107 (3)
O3—S1—C11	107.465 (17)	N1—C7—H7B	107 (11)
O3—S1—C12	108.497 (13)	C8—C7—H7A	109.8 (7)
O1—S1—C11	108.768 (14)	C8—C7—H7B	110 (1)
O1—S1—C12	106.332 (13)	H7A—C7—H7B	110 (3)
C11—S1—C12	107.613 (12)	O9—C8—C7	108.71 (3)
C10—O9—C8	111.99 (3)	O9—C8—H8A	111 (4)
C13—O14—C15	115.38 (3)	O9—C8—H8B	109 (4)
C6—N1—C2	123.97 (3)	C7—C8—H8A	111 (1)
C6—N1—C7	118.83 (3)	C7—C8—H8B	108 (1)
C2—N1—C7	117.18 (3)	H8A—C8—H8B	110 (14)
C4—N3—C2	123.61 (3)	O9—C10—C11	108.75 (3)
C4—N3—C3	118.56 (3)	O9—C10—H10A	111 (2)
C2—N3—C3	117.75 (3)	O9—C10—H10B	110 (2)
C4—N5—C6	123.93 (3)	C11—C10—H10A	111 (6)
C4—N5—C5	117.28 (3)	C11—C10—H10B	107 (6)
C6—N5—C5	118.31 (3)	H10A—C10—H10B	109 (14)
O2—C2—N3	122.12 (4)	S1—C11—C10	115.29 (2)
O2—C2—N1	121.79 (3)	S1—C11—H11A	108 (7)
N3—C2—N1	116.08 (3)	S1—C11—H11B	101 (4)
O4—C4—N3	122.53 (4)	C10—C11—H11A	111 (6)
O4—C4—N5	121.47 (4)	C10—C11—H11B	111 (1)
N3—C4—N5	115.97 (3)	H11A—C11—H11B	110 (5)
O6—C6—N1	122.44 (3)	S1—C12—C13	113.215 (17)
O6—C6—N5	121.84 (3)	S1—C12—H12A	106 (3)
N1—C6—N5	115.71 (3)	S1—C12—H12B	105 (3)
N3—C3—H3B	107 (11)	C13—C12—H12A	110 (11)
N3—C3—H3A	108 (2)	C13—C12—H12B	113 (10)
N3—C3—H3C	109 (2)	H12A—C12—H12B	110 (10)
H3B—C3—H3A	111 (2)	O14—C13—O5	124.51 (3)
H3B—C3—H3C	111 (2)	O14—C13—C12	110.41 (3)
H3A—C3—H3C	111 (9)	O5—C13—C12	125.09 (3)
N5—C5—H5C	106.5 (5)	O14—C15—H15C	108 (5)
N5—C5—H5A	109 (5)	O14—C15—H15A	108 (10)
N5—C5—H5B	109.7 (5)	O14—C15—H15B	108.2 (9)
H5C—C5—H5A	111 (7)	H15C—C15—H15A	111 (5)
H5C—C5—H5B	111 (14)	H15C—C15—H15B	111 (4)
H5A—C5—H5B	110 (8)	H15A—C15—H15B	111 (5)
N1—C7—C8	112.57 (2)
S1—C11—C10—O9	71.20 (2)	N3—C2—N1—C7	176.50 (2)
S1—C11—C10—H10A	−51 (3)	N5—C4—N3—C2	10.02 (2)
S1—C11—C10—H10B	−170 (3)	N5—C4—N3—C3	−173.49 (2)
S1—C12—C13—O14	−139.67 (2)	N5—C6—N1—C2	4.56 (2)
S1—C12—C13—O5	40.85 (3)	N5—C6—N1—C7	−173.92 (2)
O2—C2—N3—C4	175.49 (2)	C2—N3—C3—H3B	156 (2)
O2—C2—N3—C3	−1.02 (2)	C2—N3—C3—H3A	36 (5)
O2—C2—N1—C6	176.77 (2)	C2—N3—C3—H3C	−84 (5)
O2—C2—N1—C7	−4.72 (2)	C2—N1—C7—C8	−82.03 (3)
O4—C4—N3—C2	−171.68 (2)	C2—N1—C7—H7A	39 (2)
O4—C4—N3—C3	4.81 (2)	C2—N1—C7—H7B	156 (2)
O4—C4—N5—C6	174.53 (2)	C4—N3—C3—H3B	−21 (2)
O4—C4—N5—C5	2.61 (2)	C4—N3—C3—H3A	−140 (6)
O6—C6—N1—C2	−174.76 (2)	C4—N3—C3—H3C	99 (6)
O6—C6—N1—C7	6.75 (2)	C4—N5—C5—H5C	−175.4 (3)
O6—C6—N5—C4	179.60 (2)	C4—N5—C5—H5A	−56 (6)
O6—C6—N5—C5	−8.56 (2)	C4—N5—C5—H5B	65.0 (3)
O9—C10—C11—H11A	−52 (9)	C6—N1—C7—C8	96.56 (2)
O9—C10—C11—H11B	−174.5 (10)	C6—N1—C7—H7A	−143 (2)
O9—C8—C7—N1	−74.92 (3)	C6—N1—C7—H7B	−25 (2)
O9—C8—C7—H7A	166 (1)	C6—N5—C5—H5C	12 (2)
O9—C8—C7—H7B	45 (10)	C6—N5—C5—H5A	132 (6)
O1—S1—C11—C10	50.91 (2)	C6—N5—C5—H5B	−107 (2)
O1—S1—C11—H11A	176 (4)	C7—C8—O9—C10	−178.28 (3)
O1—S1—C11—H11B	−69 (4)	C8—O9—C10—C11	167.88 (2)
O1—S1—C12—C13	177.53 (2)	C8—O9—C10—H10A	−70 (10)
O1—S1—C12—H12A	−61.7 (6)	C8—O9—C10—H10B	51 (10)
O1—S1—C12—H12B	54.4 (6)	C10—O9—C8—H8A	60 (10)
O3—S1—C11—C10	179.44 (2)	C10—O9—C8—H8B	−61 (10)
O3—S1—C11—H11A	−56 (3)	C10—C11—S1—C12	−63.90 (3)
O3—S1—C11—H11B	60 (6)	C11—S1—C12—C13	−66.06 (3)
O3—S1—C12—C13	49.94 (2)	C11—S1—C12—H12A	55 (9)
O3—S1—C12—H12A	171 (8)	C11—S1—C12—H12B	171 (9)
O3—S1—C12—H12B	−73 (8)	C12—S1—C11—H11A	61 (9)
O5—C13—O14—C15	−1.02 (2)	C12—S1—C11—H11B	176 (2)
O5—C13—C12—H12A	−78 (4)	C12—C13—O14—C15	179.49 (2)
O5—C13—C12—H12B	159 (4)	C13—O14—C15—H15C	179 (2)
O14—C13—C12—H12A	102 (3)	C13—O14—C15—H15A	−61 (3)
O14—C13—C12—H12B	−21 (3)	C13—O14—C15—H15B	59 (4)
N1—C6—N5—C4	0.27 (2)	H7A—C7—C8—H8A	−72 (11)
N1—C6—N5—C5	172.11 (2)	H7A—C7—C8—H8B	48 (10)
N1—C2—N3—C4	−5.73 (2)	H7B—C7—C8—H8A	166 (9)
N1—C2—N3—C3	177.76 (2)	H7B—C7—C8—H8B	−74 (9)
N1—C7—C8—H8A	47 (6)	H10A—C10—C11—H11A	−174 (9)
N1—C7—C8—H8B	167 (6)	H10A—C10—C11—H11B	64 (9)
N3—C4—N5—C6	−7.15 (2)	H10B—C10—C11—H11A	67 (9)
N3—C4—N5—C5	−179.07 (2)	H10B—C10—C11—H11B	−55 (9)
N3—C2—N1—C6	−2.01 (2)