Crystal structure of N-[(2S,5R)-4-oxo-2,3-diphenyl-1,3-thia­zinan-5-yl]acetamide 0.375-hydrate

The crystal structure of the title compound displays boat and half-chair configurations of the thia­zine ring.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in solvent or counterion
• R factor = 0.066
• wR factor = 0.216
• Data-to-parameter ratio = 19.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C10    --  C11     ..        7.8 su
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          3 Check

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C22    --  C23     ..        5.2 su
PLAT241_ALERT_2_C High      Ueq as Compared to Neighbors for .....        C12 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0062 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H7     ..  H15     ..       1.98 Ang.
PLAT414_ALERT_2_C Short Intra D-H..H-X       H4N    ..  H33     ..       1.90 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.090 Check
PLAT918_ALERT_3_C Reflection(s) with I(obs) much smaller I(calc) .          5 Check

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C36 H36 N4 O4.75 S2
            Atom count from _chemical_formula_moiety:C36 H37.5 N4 O4.75 S2
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT042_ALERT_1_G Calc. and Reported MoietyFormula Strings  Differ     Please Check
PLAT045_ALERT_1_G Calculated and Reported Z Differ by ............       0.13 Ratio
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT Unusually Large.       0.14 Report
PLAT152_ALERT_1_G The Supplied and Calc. Volume s.u. Differ by ...          2 Units
PLAT302_ALERT_4_G Anion/Solvent Disorder ............ Percentage =        100 Note
PLAT311_ALERT_2_G Isolated Disordered Oxygen Atom (No H's ?) .....        O5B Check
PLAT311_ALERT_2_G Isolated Disordered Oxygen Atom (No H's ?) .....        O5C Check
PLAT791_ALERT_4_G The Model has Chirality at C7      .............          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C15     .............          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C19     .............          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C33     .............          R Verify
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   2 ALERT level B = A potentially serious problem, consider carefully
   7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  15 ALERT level G = General information/check it is not something unexpected

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XSHELL (Bruker, 2001); software used to prepare material for publication: ORTEP-3 for Windows (Farrugia, 2012).

N-[(2S,5R)-4-Oxo-2,3-diphenyl-1,3-thiazinan-5-yl]acetamide 0.375-hydrate

Crystal data

2C18H18N2O2S·0.75OH2O	Dx = 1.233 Mg m^−3
Mr = 664.81	Melting point: 451(2) K
Tetragonal, P41212	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 4abw 2nw	Cell parameters from 6252 reflections
a = 13.3438 (12) Å	θ = 2.2–26.4°
c = 40.237 (7) Å	µ = 0.19 mm^−1
V = 7164.6 (16) Å^3	T = 298 K
Z = 8	Cube, colorless
F(000) = 2800	0.28 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer	8891 independent reflections
Radiation source: fine-focus sealed tube	6254 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
Detector resolution: 8.34 pixels mm^-1	θmax = 28.3°, θmin = 1.6°
φ and ω scans	h = −16→17
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −17→16
Tmin = 0.948, Tmax = 0.962	l = −53→53
56028 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.066	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.216	w = 1/[σ^2(Fo^2) + (0.140P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.008
8891 reflections	Δρmax = 0.75 e Å^−3
448 parameters	Δρmin = −0.48 e Å^−3
0 restraints	Absolute structure: Flack (1983), 3769 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.10 (10)

Special details

Experimental. Absorption correction: SADABS was used for absorption correction. R(int) was 0.0331 before and 0.0128 after correction. The Ratio of minimum to maximum transmission is 0.8482. The λ/2 correction factor is 0.0015.

The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of ω scans each set at different φ and/or 2θ angles and each scan (10 s exposure) covering -0.300° degrees in ω. The crystal to detector distance was 5.82 cm.

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O5A	0.0057 (15)	0.053 (2)	0.2410 (7)	0.178 (10)	0.25
C1	0.2504 (3)	−0.0827 (2)	0.18198 (8)	0.0489 (7)
C2	0.1531 (3)	−0.1098 (3)	0.18700 (10)	0.0651 (9)
H2	0.1094	−0.0680	0.1985	0.078*
C3	0.1199 (4)	−0.2031 (4)	0.17437 (13)	0.0878 (15)
H3	0.0530	−0.2212	0.1768	0.105*
C4	0.1842 (5)	−0.2668 (3)	0.15865 (14)	0.0923 (16)
H4	0.1618	−0.3286	0.1510	0.111*
C5	0.2808 (4)	−0.2392 (3)	0.15436 (11)	0.0800 (13)
H5	0.3247	−0.2825	0.1436	0.096*
C6	0.3156 (3)	−0.1476 (3)	0.16574 (9)	0.0625 (9)
H6	0.3822	−0.1297	0.1625	0.075*
C7	0.3648 (3)	0.0213 (3)	0.21946 (8)	0.0509 (7)
H7	0.4174	0.0648	0.2105	0.061*
C8	0.4137 (3)	−0.0748 (3)	0.22965 (8)	0.0562 (8)
C9	0.3653 (3)	−0.1439 (3)	0.24980 (10)	0.0706 (10)
H9	0.3010	−0.1323	0.2579	0.085*
C10	0.4193 (5)	−0.2344 (3)	0.25755 (12)	0.0907 (16)
H10	0.3891	−0.2829	0.2708	0.109*
C11	0.5109 (5)	−0.2497 (4)	0.24620 (14)	0.0932 (16)
H11	0.5439	−0.3088	0.2517	0.112*
C12	0.5571 (4)	−0.1833 (5)	0.22722 (15)	0.0994 (17)
H12	0.6211	−0.1966	0.2192	0.119*
C13	0.5102 (3)	−0.0938 (4)	0.21928 (11)	0.0739 (10)
H13	0.5442	−0.0461	0.2068	0.089*
C14	0.2462 (2)	0.0994 (2)	0.18183 (8)	0.0499 (7)
C15	0.2878 (3)	0.1931 (2)	0.19744 (9)	0.0545 (7)
H15	0.3607	0.1932	0.1945	0.065*
C16	0.2647 (4)	0.1940 (3)	0.23457 (10)	0.0724 (10)
H16A	0.1927	0.1975	0.2377	0.087*
H16B	0.2940	0.2535	0.2444	0.087*
C17	0.2967 (3)	0.3685 (2)	0.17969 (9)	0.0577 (8)
C18	0.2486 (4)	0.4517 (3)	0.16103 (11)	0.0772 (12)
H18A	0.2521	0.5121	0.1739	0.116*
H18B	0.1798	0.4353	0.1568	0.116*
H18C	0.2830	0.4614	0.1403	0.116*
C19	0.6796 (2)	0.1320 (2)	0.09363 (8)	0.0481 (7)
H19	0.6662	0.1120	0.0706	0.058*
C20	0.7810 (2)	0.0882 (2)	0.10234 (9)	0.0516 (7)
C21	0.8070 (3)	0.0618 (3)	0.13434 (10)	0.0612 (8)
H21	0.7602	0.0671	0.1514	0.073*
C22	0.9023 (3)	0.0278 (3)	0.14103 (15)	0.0826 (13)
H22	0.9196	0.0100	0.1626	0.099*
C23	0.9725 (3)	0.0197 (4)	0.11586 (16)	0.0866 (15)
H23	1.0374	−0.0012	0.1207	0.104*
C24	0.9467 (3)	0.0419 (4)	0.08473 (16)	0.0900 (15)
H24	0.9933	0.0340	0.0677	0.108*
C25	0.8515 (3)	0.0765 (3)	0.07738 (12)	0.0693 (10)
H25	0.8347	0.0921	0.0555	0.083*
C26	0.5686 (2)	−0.0093 (2)	0.10451 (8)	0.0492 (7)
C27	0.5836 (3)	−0.0874 (3)	0.12672 (11)	0.0614 (8)
H27	0.6106	−0.0748	0.1476	0.074*
C28	0.5582 (3)	−0.1838 (3)	0.11770 (13)	0.0726 (11)
H28	0.5669	−0.2361	0.1327	0.087*
C29	0.5199 (4)	−0.2029 (3)	0.08654 (14)	0.0817 (13)
H29	0.5027	−0.2681	0.0806	0.098*
C30	0.5071 (4)	−0.1261 (4)	0.06417 (13)	0.0899 (15)
H30	0.4823	−0.1396	0.0430	0.108*
C31	0.5311 (3)	−0.0281 (3)	0.07304 (10)	0.0678 (10)
H31	0.5220	0.0240	0.0580	0.081*
C32	0.5461 (2)	0.1382 (2)	0.13924 (8)	0.0490 (7)
C33	0.5743 (3)	0.2454 (3)	0.14941 (9)	0.0542 (8)
H33	0.5249	0.2891	0.1387	0.065*
C34	0.6759 (3)	0.2826 (2)	0.13793 (10)	0.0570 (8)
H34A	0.7286	0.2442	0.1486	0.068*
H34B	0.6842	0.3525	0.1439	0.068*
C35	0.6035 (3)	0.1985 (4)	0.20735 (10)	0.0707 (10)
C36	0.5771 (5)	0.2170 (5)	0.24334 (11)	0.1019 (17)
H36A	0.5455	0.2813	0.2455	0.153*
H36B	0.6371	0.2157	0.2565	0.153*
H36C	0.5321	0.1657	0.2509	0.153*
N1	0.28612 (19)	0.01260 (19)	0.19383 (7)	0.0474 (6)
N2	0.2471 (3)	0.2807 (2)	0.18125 (9)	0.0601 (7)
H2N	0.193 (5)	0.265 (4)	0.1701 (12)	0.100 (17)*
N3	0.59653 (19)	0.09217 (19)	0.11341 (7)	0.0481 (6)
N4	0.5591 (3)	0.2575 (3)	0.18477 (9)	0.0633 (8)
H4N	0.511 (3)	0.305 (3)	0.1853 (9)	0.053 (10)*
O1	0.1807 (2)	0.10192 (19)	0.16054 (7)	0.0673 (7)
O2	0.3791 (2)	0.3763 (2)	0.19349 (8)	0.0734 (7)
O3	0.47621 (19)	0.09644 (19)	0.15238 (7)	0.0629 (6)
O4	0.6614 (3)	0.1312 (3)	0.19895 (8)	0.0841 (9)
S1	0.31262 (10)	0.08417 (8)	0.25589 (2)	0.0726 (3)
S2	0.68356 (7)	0.26844 (7)	0.09362 (3)	0.0624 (2)
O5C	0.9973 (9)	0.2040 (12)	0.2631 (3)	0.092 (4)	0.25
O5B	0.8745 (12)	0.1255 (12)	0.2500	0.270 (15)	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O5A	0.092 (12)	0.22 (3)	0.22 (3)	0.038 (16)	0.064 (14)	0.00 (2)
C1	0.0553 (18)	0.0383 (15)	0.0533 (15)	−0.0032 (13)	−0.0101 (14)	0.0055 (12)
C2	0.0536 (19)	0.064 (2)	0.078 (2)	−0.0075 (16)	−0.0073 (17)	0.0157 (18)
C3	0.079 (3)	0.070 (3)	0.114 (3)	−0.028 (2)	−0.036 (3)	0.023 (3)
C4	0.115 (4)	0.046 (2)	0.116 (4)	−0.008 (3)	−0.047 (3)	0.002 (2)
C5	0.103 (4)	0.054 (2)	0.083 (3)	0.014 (2)	−0.024 (2)	−0.013 (2)
C6	0.066 (2)	0.061 (2)	0.0607 (19)	0.0083 (17)	−0.0060 (17)	−0.0083 (16)
C7	0.0494 (17)	0.0505 (17)	0.0527 (16)	−0.0001 (13)	−0.0053 (13)	0.0027 (13)
C8	0.059 (2)	0.0545 (19)	0.0552 (16)	−0.0001 (15)	−0.0102 (15)	−0.0019 (14)
C9	0.074 (3)	0.069 (2)	0.069 (2)	−0.0090 (19)	−0.006 (2)	0.0174 (19)
C10	0.132 (5)	0.058 (2)	0.083 (3)	−0.016 (3)	−0.038 (3)	0.017 (2)
C11	0.099 (4)	0.083 (3)	0.097 (3)	0.023 (3)	−0.037 (3)	0.007 (3)
C12	0.081 (3)	0.106 (4)	0.111 (4)	0.033 (3)	−0.023 (3)	0.006 (3)
C13	0.059 (2)	0.089 (3)	0.074 (2)	0.016 (2)	−0.0084 (19)	0.007 (2)
C14	0.0495 (17)	0.0416 (16)	0.0585 (17)	0.0026 (13)	−0.0020 (14)	0.0028 (13)
C15	0.0507 (17)	0.0406 (15)	0.0722 (19)	0.0010 (13)	0.0011 (15)	−0.0072 (15)
C16	0.088 (3)	0.052 (2)	0.077 (2)	0.0129 (19)	0.009 (2)	−0.0090 (18)
C17	0.062 (2)	0.0402 (16)	0.071 (2)	0.0004 (14)	0.0133 (17)	−0.0029 (14)
C18	0.104 (3)	0.0449 (19)	0.083 (3)	0.005 (2)	0.009 (2)	0.0092 (18)
C19	0.0402 (15)	0.0411 (15)	0.0630 (17)	−0.0036 (12)	0.0048 (13)	0.0051 (13)
C20	0.0445 (16)	0.0382 (15)	0.0722 (19)	−0.0046 (12)	0.0036 (14)	−0.0062 (14)
C21	0.055 (2)	0.0498 (18)	0.078 (2)	0.0039 (16)	−0.0041 (17)	−0.0032 (16)
C22	0.066 (3)	0.056 (2)	0.126 (4)	0.0054 (19)	−0.030 (3)	−0.011 (2)
C23	0.043 (2)	0.069 (3)	0.148 (5)	0.0080 (17)	−0.008 (3)	−0.009 (3)
C24	0.052 (2)	0.083 (3)	0.135 (5)	0.004 (2)	0.031 (3)	−0.012 (3)
C25	0.056 (2)	0.060 (2)	0.091 (3)	−0.0015 (17)	0.0156 (19)	0.001 (2)
C26	0.0369 (15)	0.0466 (16)	0.0641 (17)	−0.0015 (12)	0.0024 (13)	0.0020 (14)
C27	0.0502 (19)	0.0510 (19)	0.083 (2)	0.0040 (15)	0.0034 (17)	0.0045 (17)
C28	0.058 (2)	0.0470 (19)	0.113 (3)	0.0028 (16)	0.003 (2)	0.007 (2)
C29	0.070 (3)	0.049 (2)	0.126 (4)	−0.0124 (18)	0.006 (3)	−0.014 (2)
C30	0.089 (3)	0.093 (3)	0.088 (3)	−0.035 (3)	0.002 (3)	−0.015 (3)
C31	0.063 (2)	0.070 (2)	0.070 (2)	−0.0136 (18)	−0.0083 (18)	−0.0008 (18)
C32	0.0362 (15)	0.0483 (17)	0.0624 (17)	0.0014 (12)	0.0060 (13)	0.0011 (14)
C33	0.0456 (17)	0.0442 (16)	0.073 (2)	0.0081 (13)	0.0025 (15)	−0.0023 (14)
C34	0.0499 (18)	0.0363 (15)	0.085 (2)	−0.0017 (13)	0.0023 (16)	0.0065 (15)
C35	0.062 (2)	0.079 (3)	0.071 (2)	−0.014 (2)	−0.0045 (18)	−0.005 (2)
C36	0.108 (4)	0.129 (5)	0.069 (2)	−0.034 (3)	0.008 (3)	−0.017 (3)
N1	0.0457 (14)	0.0392 (13)	0.0574 (14)	0.0019 (10)	−0.0038 (11)	−0.0014 (11)
N2	0.0589 (18)	0.0402 (15)	0.081 (2)	0.0012 (12)	−0.0044 (16)	−0.0011 (13)
N3	0.0396 (13)	0.0426 (13)	0.0622 (14)	0.0000 (10)	0.0053 (11)	0.0027 (11)
N4	0.0577 (18)	0.0550 (18)	0.0772 (19)	0.0000 (15)	0.0121 (15)	−0.0127 (15)
O1	0.0695 (16)	0.0490 (13)	0.0834 (16)	−0.0016 (12)	−0.0239 (14)	0.0030 (12)
O2	0.0626 (17)	0.0519 (15)	0.106 (2)	−0.0026 (12)	0.0136 (15)	−0.0058 (14)
O3	0.0511 (13)	0.0584 (14)	0.0791 (16)	−0.0047 (11)	0.0173 (12)	−0.0021 (12)
O4	0.0760 (19)	0.094 (2)	0.0821 (18)	0.0198 (17)	−0.0026 (16)	0.0077 (17)
S1	0.0985 (8)	0.0656 (6)	0.0537 (4)	0.0074 (5)	0.0004 (5)	−0.0062 (4)
S2	0.0592 (5)	0.0476 (5)	0.0805 (6)	−0.0027 (4)	0.0059 (4)	0.0147 (4)
O5C	0.059 (7)	0.114 (11)	0.103 (9)	0.018 (7)	0.012 (6)	−0.027 (8)
O5B	0.172 (12)	0.172 (12)	0.47 (4)	0.015 (16)	−0.096 (18)	−0.096 (18)

Geometric parameters (Å, º)

O5A—O5A^i	1.33 (4)	C19—C20	1.515 (4)
C1—C2	1.363 (5)	C19—S2	1.822 (3)
C1—C6	1.391 (5)	C19—H19	0.9800
C1—N1	1.439 (4)	C20—C21	1.379 (5)
C2—C3	1.415 (6)	C20—C25	1.384 (5)
C2—H2	0.9300	C21—C22	1.377 (6)
C3—C4	1.363 (8)	C21—H21	0.9300
C3—H3	0.9300	C22—C23	1.384 (8)
C4—C5	1.352 (8)	C22—H22	0.9300
C4—H4	0.9300	C23—C24	1.333 (7)
C5—C6	1.385 (6)	C23—H23	0.9300
C5—H5	0.9300	C24—C25	1.384 (7)
C6—H6	0.9300	C24—H24	0.9300
C7—N1	1.477 (4)	C25—H25	0.9300
C7—C8	1.496 (5)	C26—C31	1.385 (5)
C7—S1	1.827 (4)	C26—C27	1.388 (5)
C7—H7	0.9800	C26—N3	1.449 (4)
C8—C13	1.377 (6)	C27—C28	1.379 (6)
C8—C9	1.388 (5)	C27—H27	0.9300
C9—C10	1.440 (7)	C28—C29	1.378 (7)
C9—H9	0.9300	C28—H28	0.9300
C10—C11	1.321 (8)	C29—C30	1.376 (7)
C10—H10	0.9300	C29—H29	0.9300
C11—C12	1.322 (8)	C30—C31	1.392 (6)
C11—H11	0.9300	C30—H30	0.9300
C12—C13	1.386 (7)	C31—H31	0.9300
C12—H12	0.9300	C32—O3	1.208 (4)
C13—H13	0.9300	C32—N3	1.382 (4)
C14—O1	1.225 (4)	C32—C33	1.535 (5)
C14—N1	1.363 (4)	C33—N4	1.446 (5)
C14—C15	1.505 (5)	C33—C34	1.516 (5)
C15—N2	1.444 (5)	C33—H33	0.9800
C15—C16	1.525 (5)	C34—S2	1.796 (4)
C15—H15	0.9800	C34—H34A	0.9700
C16—S1	1.814 (4)	C34—H34B	0.9700
C16—H16A	0.9700	C35—O4	1.232 (5)
C16—H16B	0.9700	C35—N4	1.340 (6)
C17—O2	1.236 (5)	C35—C36	1.510 (6)
C17—N2	1.346 (5)	C36—H36A	0.9600
C17—C18	1.486 (6)	C36—H36B	0.9600
C18—H18A	0.9600	C36—H36C	0.9600
C18—H18B	0.9600	N2—H2N	0.87 (6)
C18—H18C	0.9600	N4—H4N	0.90 (4)
C19—N3	1.464 (4)
C2—C1—C6	120.0 (3)	C21—C20—C19	122.6 (3)
C2—C1—N1	120.1 (3)	C25—C20—C19	118.8 (3)
C6—C1—N1	119.9 (3)	C22—C21—C20	119.9 (4)
C1—C2—C3	118.6 (4)	C22—C21—H21	120.1
C1—C2—H2	120.7	C20—C21—H21	120.1
C3—C2—H2	120.7	C21—C22—C23	120.5 (5)
C4—C3—C2	121.2 (5)	C21—C22—H22	119.7
C4—C3—H3	119.4	C23—C22—H22	119.7
C2—C3—H3	119.4	C24—C23—C22	119.7 (4)
C5—C4—C3	119.3 (4)	C24—C23—H23	120.2
C5—C4—H4	120.4	C22—C23—H23	120.2
C3—C4—H4	120.4	C23—C24—C25	120.8 (4)
C4—C5—C6	121.2 (4)	C23—C24—H24	119.6
C4—C5—H5	119.4	C25—C24—H24	119.6
C6—C5—H5	119.4	C24—C25—C20	120.4 (5)
C5—C6—C1	119.7 (4)	C24—C25—H25	119.8
C5—C6—H6	120.1	C20—C25—H25	119.8
C1—C6—H6	120.1	C31—C26—C27	120.3 (3)
N1—C7—C8	115.7 (3)	C31—C26—N3	119.3 (3)
N1—C7—S1	109.0 (2)	C27—C26—N3	120.4 (3)
C8—C7—S1	109.9 (2)	C28—C27—C26	119.8 (4)
N1—C7—H7	107.3	C28—C27—H27	120.1
C8—C7—H7	107.3	C26—C27—H27	120.1
S1—C7—H7	107.3	C29—C28—C27	120.2 (4)
C13—C8—C9	119.3 (4)	C29—C28—H28	119.9
C13—C8—C7	118.9 (4)	C27—C28—H28	119.9
C9—C8—C7	121.8 (3)	C30—C29—C28	120.3 (4)
C8—C9—C10	116.8 (4)	C30—C29—H29	119.9
C8—C9—H9	121.6	C28—C29—H29	119.9
C10—C9—H9	121.6	C29—C30—C31	120.2 (4)
C11—C10—C9	121.2 (5)	C29—C30—H30	119.9
C11—C10—H10	119.4	C31—C30—H30	119.9
C9—C10—H10	119.4	C26—C31—C30	119.3 (4)
C10—C11—C12	121.8 (5)	C26—C31—H31	120.4
C10—C11—H11	119.1	C30—C31—H31	120.4
C12—C11—H11	119.1	O3—C32—N3	120.0 (3)
C11—C12—C13	120.0 (5)	O3—C32—C33	120.1 (3)
C11—C12—H12	120.0	N3—C32—C33	119.7 (3)
C13—C12—H12	120.0	N4—C33—C34	112.9 (3)
C8—C13—C12	120.8 (5)	N4—C33—C32	109.4 (3)
C8—C13—H13	119.6	C34—C33—C32	116.3 (3)
C12—C13—H13	119.6	N4—C33—H33	105.8
O1—C14—N1	123.4 (3)	C34—C33—H33	105.8
O1—C14—C15	122.1 (3)	C32—C33—H33	105.8
N1—C14—C15	114.5 (3)	C33—C34—S2	108.6 (3)
N2—C15—C14	110.3 (3)	C33—C34—H34A	110.0
N2—C15—C16	111.1 (3)	S2—C34—H34A	110.0
C14—C15—C16	109.9 (3)	C33—C34—H34B	110.0
N2—C15—H15	108.5	S2—C34—H34B	110.0
C14—C15—H15	108.5	H34A—C34—H34B	108.3
C16—C15—H15	108.5	O4—C35—N4	121.3 (4)
C15—C16—S1	112.7 (2)	O4—C35—C36	121.8 (5)
C15—C16—H16A	109.1	N4—C35—C36	116.8 (5)
S1—C16—H16A	109.1	C14—N1—C1	120.3 (3)
C15—C16—H16B	109.1	C14—N1—C7	117.3 (3)
S1—C16—H16B	109.1	C1—N1—C7	122.4 (3)
H16A—C16—H16B	107.8	C17—N2—C15	122.7 (3)
O2—C17—N2	119.3 (3)	C17—N2—H2N	126 (4)
O2—C17—C18	123.2 (3)	C15—N2—H2N	111 (4)
N2—C17—C18	117.5 (4)	C32—N3—C26	118.4 (3)
N3—C19—C20	114.2 (3)	C32—N3—C19	128.0 (3)
N3—C19—S2	112.6 (2)	C26—N3—C19	113.5 (2)
C20—C19—S2	111.1 (2)	C35—N4—C33	122.7 (3)
N3—C19—H19	106.1	C35—N4—H4N	135 (2)
C20—C19—H19	106.1	C33—N4—H4N	102 (2)
S2—C19—H19	106.1	C16—S1—C7	97.23 (17)
C21—C20—C25	118.6 (3)	C34—S2—C19	95.94 (15)
C6—C1—C2—C3	−2.1 (5)	C29—C30—C31—C26	0.5 (7)
N1—C1—C2—C3	178.6 (3)	O3—C32—C33—N4	36.7 (4)
C1—C2—C3—C4	2.6 (7)	N3—C32—C33—N4	−147.8 (3)
C2—C3—C4—C5	−1.7 (7)	O3—C32—C33—C34	166.0 (3)
C3—C4—C5—C6	0.2 (7)	N3—C32—C33—C34	−18.5 (4)
C4—C5—C6—C1	0.2 (6)	N4—C33—C34—S2	−177.7 (2)
C2—C1—C6—C5	0.8 (5)	C32—C33—C34—S2	54.8 (3)
N1—C1—C6—C5	−179.9 (3)	O1—C14—N1—C1	−1.1 (5)
N1—C7—C8—C13	106.9 (4)	C15—C14—N1—C1	177.6 (3)
S1—C7—C8—C13	−129.2 (3)	O1—C14—N1—C7	179.9 (3)
N1—C7—C8—C9	−74.5 (4)	C15—C14—N1—C7	−1.3 (4)
S1—C7—C8—C9	49.4 (4)	C2—C1—N1—C14	−62.4 (4)
C13—C8—C9—C10	−2.3 (6)	C6—C1—N1—C14	118.4 (4)
C7—C8—C9—C10	179.1 (3)	C2—C1—N1—C7	116.5 (4)
C8—C9—C10—C11	0.7 (7)	C6—C1—N1—C7	−62.7 (4)
C9—C10—C11—C12	−0.2 (8)	C8—C7—N1—C14	−174.3 (3)
C10—C11—C12—C13	1.3 (9)	S1—C7—N1—C14	61.3 (3)
C9—C8—C13—C12	3.5 (6)	C8—C7—N1—C1	6.7 (4)
C7—C8—C13—C12	−177.9 (4)	S1—C7—N1—C1	−117.7 (3)
C11—C12—C13—C8	−3.0 (8)	O2—C17—N2—C15	−2.4 (6)
O1—C14—C15—N2	−6.0 (5)	C18—C17—N2—C15	177.4 (3)
N1—C14—C15—N2	175.3 (3)	C14—C15—N2—C17	−152.0 (3)
O1—C14—C15—C16	116.8 (4)	C16—C15—N2—C17	85.9 (4)
N1—C14—C15—C16	−61.9 (4)	O3—C32—N3—C26	−4.8 (5)
N2—C15—C16—S1	179.1 (3)	C33—C32—N3—C26	179.7 (3)
C14—C15—C16—S1	56.7 (4)	O3—C32—N3—C19	177.3 (3)
N3—C19—C20—C21	−34.8 (4)	C33—C32—N3—C19	1.8 (5)
S2—C19—C20—C21	93.9 (3)	C31—C26—N3—C32	117.9 (4)
N3—C19—C20—C25	147.0 (3)	C27—C26—N3—C32	−64.9 (4)
S2—C19—C20—C25	−84.3 (3)	C31—C26—N3—C19	−63.9 (4)
C25—C20—C21—C22	2.0 (5)	C27—C26—N3—C19	113.2 (3)
C19—C20—C21—C22	−176.3 (3)	C20—C19—N3—C32	104.5 (4)
C20—C21—C22—C23	0.0 (6)	S2—C19—N3—C32	−23.5 (4)
C21—C22—C23—C24	−2.2 (7)	C20—C19—N3—C26	−73.5 (3)
C22—C23—C24—C25	2.4 (8)	S2—C19—N3—C26	158.6 (2)
C23—C24—C25—C20	−0.4 (7)	O4—C35—N4—C33	1.1 (6)
C21—C20—C25—C24	−1.8 (6)	C36—C35—N4—C33	−177.4 (4)
C19—C20—C25—C24	176.5 (4)	C34—C33—N4—C35	−74.5 (4)
C31—C26—C27—C28	−1.9 (6)	C32—C33—N4—C35	56.6 (4)
N3—C26—C27—C28	−179.0 (3)	C15—C16—S1—C7	−1.7 (4)
C26—C27—C28—C29	1.3 (6)	N1—C7—S1—C16	−53.5 (3)
C27—C28—C29—C30	0.2 (7)	C8—C7—S1—C16	178.7 (3)
C28—C29—C30—C31	−1.1 (7)	C33—C34—S2—C19	−65.8 (2)
C27—C26—C31—C30	1.0 (6)	N3—C19—S2—C34	50.5 (3)
N3—C26—C31—C30	178.1 (4)	C20—C19—S2—C34	−79.1 (2)

Symmetry code: (i) −y, −x, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1	0.88 (6)	2.22 (5)	2.678 (4)	113 (5)
N4—H4N···O2	0.90 (4)	2.03 (4)	2.899 (5)	162 (4)
C7—H7···O3	0.98	2.50	3.241 (4)	132
C21—H21···O4	0.93	2.48	3.375 (5)	162