1,4-Bis[(Z)-2-(3-mesityl-3-methyl­cyclo­butyl)-2-(thio­semicarbazono)eth­yl]piperazine dimethyl sulfoxide disolvate

The structure of the title compound, C₃₈H₅₆N₈S₂·2C₂H₆OS, has been determined by single-crystal diffractometry and is compared with the structures of other compounds containing the thio­semicarbazide group. The structure is stabilized by N—H...S hydrogen bonding, resulting in the formation of infinite chains parallel to the [010] axis. The thio­semicarbazone group has an E configuration.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in solvent or counterion
• R factor = 0.058
• wR factor = 0.174
• Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.76
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.21 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.76 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C14
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for       S44A
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        S55
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      33.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C19

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  12 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1,4-Bis{[(2Z)-2-(3-mesityl-3-methylcyclobutyl)-2-one thiosemicarbazono]ethyl} piperazine dimethylsulfoxide disolvate

Crystal data

C38H56N8S2·2C2H6OS	F(000) = 1824
Mr = 845.28	Dx = 1.149 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 38974 reflections
a = 17.861 (11) Å	θ = 1.5–27.2°
b = 13.386 (6) Å	µ = 0.24 mm^−1
c = 20.451 (13) Å	T = 293 K
β = 91.744 (5)°	Prism, yellow
V = 4887 (5) Å^3	0.34 × 0.30 × 0.21 mm
Z = 4

Data collection

Stoe IPDS 2 diffractometer	8599 independent reflections
Radiation source: fine-focus sealed tube	4458 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
Detector resolution: 6.67 pixels mm^-1	θmax = 25.0°, θmin = 1.5°
ω scans	h = −21→21
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −15→15
Tmin = 0.876, Tmax = 0.953	l = −24→24
25636 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.174	H-atom parameters constrained
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0946P)^2] where P = (Fo^2 + 2Fc^2)/3
8599 reflections	(Δ/σ)max = 0.009
548 parameters	Δρmax = 0.80 e Å^−3
33 restraints	Δρmin = −0.29 e Å^−3

Special details

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)
S1	0.28838 (6)	0.45777 (8)	0.09492 (7)	0.0910 (4)
N1	0.42945 (18)	0.5130 (2)	0.07941 (16)	0.0802 (9)
H1A	0.4747	0.4988	0.0694	0.096*
H1B	0.4179	0.5730	0.0901	0.096*
N2	0.40164 (17)	0.3497 (2)	0.06075 (15)	0.0699 (8)
H2	0.3699	0.3023	0.0537	0.084*
N3	0.47759 (16)	0.3319 (2)	0.05408 (14)	0.0665 (8)
N4	0.38578 (15)	0.14697 (19)	0.07573 (12)	0.0555 (7)
C1	0.3772 (2)	0.4417 (3)	0.07830 (18)	0.0664 (9)
C2	0.4971 (2)	0.2426 (3)	0.03972 (16)	0.0625 (9)
C3	0.4445 (2)	0.1565 (3)	0.02739 (17)	0.0675 (9)
H3A	0.4209	0.1644	−0.0156	0.081*
H3B	0.4734	0.0951	0.0271	0.081*
C4	0.3342 (2)	0.0661 (3)	0.05897 (16)	0.0624 (9)
H4A	0.3611	0.0032	0.0589	0.075*
H4B	0.3127	0.0770	0.0154	0.075*
C5	0.27279 (19)	0.0611 (3)	0.10715 (15)	0.0589 (8)
H5A	0.2440	0.1225	0.1052	0.071*
H5B	0.2394	0.0062	0.0958	0.071*
C6	0.5778 (2)	0.2233 (3)	0.03113 (17)	0.0649 (9)
H6	0.5860	0.2060	−0.0147	0.078*
C7	0.6362 (2)	0.2996 (3)	0.05362 (19)	0.0719 (10)
H7A	0.6202	0.3419	0.0891	0.086*
H7B	0.6558	0.3394	0.0183	0.086*
C8	0.6889 (2)	0.2128 (3)	0.07627 (17)	0.0665 (9)
C9	0.6180 (2)	0.1467 (3)	0.07553 (17)	0.0669 (9)
H9A	0.6247	0.0821	0.0550	0.080*
H9B	0.5960	0.1395	0.1181	0.080*
C10	0.7418 (2)	0.1829 (4)	0.0210 (2)	0.0919 (13)
H10A	0.7135	0.1769	−0.0194	0.138*
H10B	0.7652	0.1201	0.0315	0.138*
H10C	0.7796	0.2332	0.0167	0.138*
C11	0.7330 (2)	0.2226 (3)	0.14064 (19)	0.0724 (10)
C12	0.7637 (2)	0.3152 (4)	0.1604 (2)	0.0876 (12)
C13	0.7995 (3)	0.3217 (5)	0.2210 (3)	0.1138 (17)
H13	0.8191	0.3832	0.2340	0.137*
C14	0.8080 (3)	0.2418 (6)	0.2634 (3)	0.1155 (19)
C15	0.7811 (3)	0.1509 (5)	0.2414 (3)	0.1029 (16)
H15	0.7875	0.0952	0.2681	0.123*
C16	0.7448 (2)	0.1390 (4)	0.1807 (2)	0.0825 (12)
C17	0.7237 (3)	0.0337 (3)	0.1614 (3)	0.1063 (15)
H17A	0.7315	0.0245	0.1156	0.159*
H17B	0.6719	0.0224	0.1703	0.159*
H17C	0.7543	−0.0127	0.1861	0.159*
C18	0.7624 (3)	0.4084 (4)	0.1185 (3)	0.1219 (18)
H18A	0.7723	0.3908	0.0741	0.183*
H18B	0.8000	0.4541	0.1346	0.183*
H18C	0.7140	0.4393	0.1203	0.183*
C19	0.8471 (4)	0.2510 (6)	0.3309 (3)	0.175 (3)
H19A	0.8469	0.1873	0.3524	0.263*
H19B	0.8211	0.2990	0.3567	0.263*
H19C	0.8979	0.2725	0.3258	0.263*
S21	0.39990 (5)	−0.25809 (7)	0.14668 (5)	0.0707 (3)
N21	0.25586 (16)	−0.3095 (2)	0.14621 (13)	0.0622 (7)
H21A	0.2097	−0.2967	0.1537	0.075*
H21B	0.2682	−0.3669	0.1311	0.075*
N22	0.28530 (15)	−0.15314 (19)	0.18139 (13)	0.0618 (7)
H22	0.3175	−0.1062	0.1883	0.074*
N23	0.20997 (15)	−0.1373 (2)	0.19471 (13)	0.0575 (7)
N24	0.30364 (14)	0.04671 (18)	0.17356 (12)	0.0520 (6)
C21	0.30739 (19)	−0.2415 (2)	0.15788 (15)	0.0545 (8)
C22	0.19256 (18)	−0.0493 (2)	0.21356 (15)	0.0548 (8)
C23	0.24486 (19)	0.0390 (2)	0.22163 (16)	0.0592 (8)
H23A	0.2152	0.0997	0.2196	0.071*
H23B	0.2685	0.0357	0.2649	0.071*
C24	0.35528 (19)	0.1282 (2)	0.19045 (15)	0.0581 (8)
H24A	0.3766	0.1178	0.2341	0.070*
H24B	0.3284	0.1911	0.1901	0.070*
C25	0.41677 (18)	0.1319 (3)	0.14196 (15)	0.0588 (8)
H25A	0.4509	0.1861	0.1532	0.071*
H25B	0.4449	0.0699	0.1438	0.071*
C26	0.11384 (19)	−0.0295 (3)	0.23050 (18)	0.0638 (9)
H26	0.1129	0.0159	0.2681	0.077*
C27	0.05893 (19)	−0.1146 (3)	0.24037 (16)	0.0643 (9)
H27A	0.0500	−0.1289	0.2860	0.077*
H27B	0.0715	−0.1752	0.2170	0.077*
C29	0.0602 (2)	0.0092 (3)	0.1761 (2)	0.0742 (10)
H29A	0.0731	−0.0122	0.1326	0.089*
H29B	0.0520	0.0809	0.1775	0.089*
C28	−0.00416 (19)	−0.0529 (3)	0.20620 (17)	0.0663 (9)
C30	−0.0474 (2)	0.0099 (4)	0.2558 (2)	0.1062 (16)
H30A	−0.0125	0.0433	0.2850	0.159*
H30B	−0.0790	−0.0331	0.2805	0.159*
H30C	−0.0777	0.0586	0.2328	0.159*
C31	−0.05851 (18)	−0.1063 (3)	0.15943 (17)	0.0637 (9)
C32	−0.0865 (2)	−0.2011 (3)	0.17466 (17)	0.0685 (10)
C33	−0.1321 (2)	−0.2510 (3)	0.12988 (19)	0.0789 (11)
H33	−0.1499	−0.3139	0.1409	0.095*
C34	−0.1524 (2)	−0.2122 (4)	0.06968 (19)	0.0811 (11)
C35	−0.1286 (2)	−0.1176 (4)	0.05677 (19)	0.0825 (12)
H35	−0.1431	−0.0886	0.0170	0.099*
C36	−0.0838 (2)	−0.0624 (3)	0.1001 (2)	0.0757 (11)
C37	−0.0663 (3)	0.0441 (3)	0.0810 (3)	0.1128 (17)
H37A	−0.0738	0.0874	0.1176	0.169*
H37B	−0.0989	0.0640	0.0451	0.169*
H37C	−0.0152	0.0485	0.0682	0.169*
C38	−0.0703 (2)	−0.2533 (4)	0.23932 (19)	0.0948 (14)
H38A	−0.0683	−0.2048	0.2739	0.142*
H38B	−0.0231	−0.2874	0.2377	0.142*
H38C	−0.1093	−0.3007	0.2473	0.142*
C39	−0.1993 (3)	−0.2730 (4)	0.0210 (2)	0.1232 (19)
H39A	−0.1776	−0.3382	0.0165	0.185*
H39B	−0.2006	−0.2399	−0.0207	0.185*
H39C	−0.2493	−0.2793	0.0363	0.185*
S44A	0.0126 (2)	0.3200 (2)	0.16552 (15)	0.1130 (11)	0.821 (9)
O44A	−0.0107 (5)	0.3603 (8)	0.1014 (3)	0.170 (3)	0.821 (9)
C44A	0.0054 (5)	0.4236 (6)	0.2215 (4)	0.125 (3)	0.821 (9)
H44A	−0.0464	0.4396	0.2270	0.187*	0.821 (9)
H44B	0.0308	0.4806	0.2042	0.187*	0.821 (9)
H44C	0.0281	0.4057	0.2630	0.187*	0.821 (9)
C45A	0.1122 (5)	0.3131 (8)	0.1665 (5)	0.141 (3)	0.821 (9)
H45A	0.1275	0.2656	0.1344	0.211*	0.821 (9)
H45B	0.1303	0.2924	0.2090	0.211*	0.821 (9)
H45C	0.1324	0.3776	0.1565	0.211*	0.821 (9)
S44B	0.0500 (13)	0.3003 (12)	0.1380 (10)	0.151 (4)	0.179 (9)
O44B	0.023 (3)	0.347 (4)	0.0770 (13)	0.169 (10)	0.179 (9)
C44B	−0.005 (2)	0.384 (3)	0.188 (2)	0.126 (9)	0.179 (9)
H44D	−0.0569	0.3642	0.1848	0.189*	0.179 (9)
H44E	−0.0002	0.4510	0.1723	0.189*	0.179 (9)
H44F	0.0124	0.3799	0.2325	0.189*	0.179 (9)
C45B	0.119 (2)	0.379 (3)	0.175 (2)	0.147 (11)	0.179 (9)
H45D	0.1674	0.3624	0.1582	0.220*	0.179 (9)
H45E	0.1200	0.3703	0.2212	0.220*	0.179 (9)
H45F	0.1078	0.4476	0.1643	0.220*	0.179 (9)
S55	0.04819 (6)	0.62514 (9)	0.08527 (5)	0.0848 (3)
O55	0.09531 (17)	0.6292 (2)	0.14704 (12)	0.0981 (9)
C55	0.0575 (3)	0.7424 (3)	0.0477 (2)	0.1013 (14)
H55A	0.0313	0.7918	0.0722	0.152*
H55B	0.0367	0.7396	0.0039	0.152*
H55C	0.1095	0.7599	0.0465	0.152*
C56	0.1000 (3)	0.5530 (4)	0.0302 (2)	0.1084 (16)
H56A	0.1012	0.4847	0.0445	0.163*
H56B	0.1502	0.5783	0.0289	0.163*
H56C	0.0768	0.5568	−0.0127	0.163*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0648 (6)	0.0768 (7)	0.1310 (10)	0.0079 (5)	−0.0017 (6)	−0.0288 (6)
N1	0.072 (2)	0.0575 (18)	0.112 (3)	0.0049 (17)	0.0081 (18)	−0.0017 (17)
N2	0.066 (2)	0.0538 (17)	0.090 (2)	0.0037 (15)	0.0055 (16)	−0.0096 (15)
N3	0.0575 (18)	0.0665 (18)	0.0761 (19)	0.0048 (15)	0.0112 (15)	−0.0011 (15)
N4	0.0598 (17)	0.0545 (15)	0.0522 (15)	0.0018 (13)	0.0024 (13)	−0.0105 (12)
C1	0.069 (2)	0.056 (2)	0.074 (2)	0.0032 (19)	−0.0033 (18)	−0.0029 (17)
C2	0.065 (2)	0.063 (2)	0.060 (2)	0.0063 (19)	0.0141 (16)	−0.0030 (17)
C3	0.070 (2)	0.067 (2)	0.066 (2)	0.0001 (19)	0.0141 (18)	−0.0158 (17)
C4	0.068 (2)	0.062 (2)	0.0560 (19)	−0.0032 (18)	−0.0035 (16)	−0.0136 (16)
C5	0.061 (2)	0.0581 (19)	0.0573 (19)	−0.0025 (16)	−0.0085 (16)	−0.0104 (15)
C6	0.069 (2)	0.070 (2)	0.0575 (19)	0.0043 (19)	0.0200 (17)	−0.0047 (17)
C7	0.069 (2)	0.069 (2)	0.080 (2)	0.003 (2)	0.0207 (19)	0.0081 (19)
C8	0.060 (2)	0.073 (2)	0.068 (2)	0.0064 (19)	0.0222 (18)	−0.0018 (18)
C9	0.069 (2)	0.064 (2)	0.068 (2)	0.0081 (19)	0.0196 (18)	−0.0083 (17)
C10	0.079 (3)	0.116 (3)	0.083 (3)	0.012 (3)	0.033 (2)	−0.003 (2)
C11	0.057 (2)	0.088 (3)	0.073 (2)	0.012 (2)	0.0199 (19)	−0.003 (2)
C12	0.067 (3)	0.104 (4)	0.092 (3)	0.007 (2)	0.008 (2)	−0.015 (3)
C13	0.088 (4)	0.127 (5)	0.127 (5)	0.008 (3)	0.006 (3)	−0.030 (4)
C14	0.075 (3)	0.184 (6)	0.087 (3)	0.029 (4)	0.002 (3)	−0.025 (4)
C15	0.073 (3)	0.140 (5)	0.096 (4)	0.036 (3)	0.015 (3)	0.013 (3)
C16	0.059 (2)	0.111 (4)	0.078 (3)	0.020 (2)	0.015 (2)	0.007 (3)
C17	0.100 (4)	0.090 (3)	0.129 (4)	0.019 (3)	0.013 (3)	0.029 (3)
C18	0.123 (4)	0.097 (4)	0.146 (5)	−0.030 (3)	−0.001 (4)	−0.003 (3)
C19	0.141 (6)	0.264 (9)	0.119 (5)	0.047 (6)	−0.027 (4)	−0.031 (5)
S21	0.0622 (6)	0.0707 (6)	0.0792 (6)	0.0075 (5)	0.0041 (5)	−0.0112 (5)
N21	0.0652 (19)	0.0483 (15)	0.0735 (18)	0.0022 (15)	0.0062 (14)	−0.0020 (13)
N22	0.0532 (17)	0.0505 (16)	0.0817 (19)	0.0018 (13)	0.0026 (14)	−0.0079 (14)
N23	0.0490 (16)	0.0542 (16)	0.0694 (17)	0.0021 (13)	0.0034 (13)	−0.0072 (13)
N24	0.0560 (16)	0.0496 (15)	0.0500 (14)	−0.0032 (12)	−0.0046 (12)	−0.0075 (11)
C21	0.062 (2)	0.0478 (18)	0.0537 (18)	0.0058 (17)	0.0010 (15)	0.0065 (15)
C22	0.055 (2)	0.056 (2)	0.0540 (18)	0.0019 (16)	−0.0017 (15)	−0.0021 (15)
C23	0.062 (2)	0.0547 (19)	0.0604 (19)	−0.0002 (17)	0.0016 (16)	−0.0118 (15)
C24	0.065 (2)	0.0575 (19)	0.0521 (18)	−0.0080 (17)	−0.0024 (16)	−0.0091 (15)
C25	0.055 (2)	0.0579 (19)	0.063 (2)	−0.0045 (16)	−0.0041 (16)	−0.0108 (16)
C26	0.058 (2)	0.062 (2)	0.072 (2)	0.0035 (18)	0.0035 (17)	−0.0159 (17)
C27	0.057 (2)	0.078 (2)	0.058 (2)	0.0032 (19)	0.0003 (16)	−0.0007 (17)
C29	0.065 (2)	0.054 (2)	0.103 (3)	0.0083 (18)	−0.006 (2)	0.001 (2)
C28	0.051 (2)	0.075 (2)	0.073 (2)	0.0094 (18)	0.0015 (17)	−0.0071 (18)
C30	0.070 (3)	0.128 (4)	0.121 (4)	0.025 (3)	0.005 (3)	−0.046 (3)
C31	0.0444 (19)	0.078 (2)	0.068 (2)	0.0097 (18)	0.0024 (16)	0.0056 (19)
C32	0.053 (2)	0.095 (3)	0.058 (2)	−0.001 (2)	0.0034 (16)	0.009 (2)
C33	0.067 (2)	0.089 (3)	0.081 (3)	−0.009 (2)	−0.006 (2)	0.010 (2)
C34	0.072 (3)	0.099 (3)	0.072 (3)	0.006 (2)	−0.008 (2)	−0.005 (2)
C35	0.073 (3)	0.105 (3)	0.069 (2)	0.019 (3)	−0.012 (2)	0.013 (2)
C36	0.055 (2)	0.083 (3)	0.089 (3)	0.015 (2)	−0.003 (2)	0.011 (2)
C37	0.099 (4)	0.092 (3)	0.145 (4)	0.014 (3)	−0.034 (3)	0.038 (3)
C38	0.077 (3)	0.130 (4)	0.077 (3)	−0.031 (3)	−0.006 (2)	0.030 (3)
C39	0.134 (5)	0.136 (4)	0.096 (3)	−0.007 (4)	−0.048 (3)	−0.014 (3)
S44A	0.135 (2)	0.1055 (16)	0.0966 (17)	−0.0188 (15)	−0.0274 (14)	0.0090 (12)
O44A	0.214 (9)	0.199 (6)	0.092 (4)	0.004 (6)	−0.062 (5)	0.017 (5)
C44A	0.162 (7)	0.108 (6)	0.103 (5)	−0.006 (5)	−0.007 (5)	−0.003 (4)
C45A	0.132 (7)	0.184 (10)	0.106 (5)	0.026 (8)	−0.022 (5)	0.000 (7)
S44B	0.167 (9)	0.143 (7)	0.140 (8)	−0.021 (7)	−0.008 (8)	0.019 (7)
O44B	0.23 (2)	0.198 (17)	0.080 (15)	−0.012 (18)	−0.043 (16)	0.008 (16)
C44B	0.165 (18)	0.086 (17)	0.127 (19)	−0.001 (16)	−0.001 (18)	−0.032 (15)
C45B	0.155 (18)	0.17 (2)	0.114 (16)	−0.01 (2)	−0.014 (15)	0.00 (2)
S55	0.0773 (7)	0.1003 (8)	0.0765 (7)	−0.0039 (6)	0.0000 (5)	0.0025 (6)
O55	0.098 (2)	0.136 (3)	0.0590 (15)	−0.0207 (19)	−0.0130 (14)	0.0075 (16)
C55	0.107 (4)	0.102 (3)	0.096 (3)	0.010 (3)	0.015 (3)	0.012 (3)
C56	0.115 (4)	0.125 (4)	0.085 (3)	0.033 (3)	−0.002 (3)	0.008 (3)

Geometric parameters (Å, º)

S1—C1	1.647 (4)	N22—C21	1.340 (4)
N1—C1	1.334 (5)	N22—N23	1.397 (4)
N1—H1A	0.8600	N22—H22	0.8600
N1—H1B	0.8600	N23—C22	1.280 (4)
N2—C1	1.359 (4)	N24—C24	1.463 (4)
N2—N3	1.388 (4)	N24—C23	1.464 (4)
N2—H2	0.8600	C22—C26	1.482 (5)
N3—C2	1.281 (4)	C22—C23	1.513 (5)
N4—C4	1.456 (4)	C23—H23A	0.9700
N4—C25	1.462 (4)	C23—H23B	0.9700
N4—C3	1.469 (4)	C24—C25	1.503 (4)
C2—C6	1.480 (5)	C24—H24A	0.9700
C2—C3	1.503 (5)	C24—H24B	0.9700
C3—H3A	0.9700	C25—H25A	0.9700
C3—H3B	0.9700	C25—H25B	0.9700
C4—C5	1.497 (5)	C26—C27	1.521 (5)
C4—H4A	0.9700	C26—C29	1.536 (5)
C4—H4B	0.9700	C26—H26	0.9800
C5—N24	1.463 (4)	C27—C28	1.547 (5)
C5—H5A	0.9700	C27—H27A	0.9700
C5—H5B	0.9700	C27—H27B	0.9700
C6—C7	1.521 (5)	C29—C28	1.560 (5)
C6—C9	1.533 (5)	C29—H29A	0.9700
C6—H6	0.9800	C29—H29B	0.9700
C7—C8	1.557 (5)	C28—C31	1.520 (5)
C7—H7A	0.9700	C28—C30	1.543 (5)
C7—H7B	0.9700	C30—H30A	0.9600
C8—C11	1.519 (5)	C30—H30B	0.9600
C8—C9	1.544 (5)	C30—H30C	0.9600
C8—C10	1.548 (5)	C31—C32	1.402 (5)
C9—H9A	0.9700	C31—C36	1.410 (5)
C9—H9B	0.9700	C32—C33	1.380 (5)
C10—H10A	0.9600	C32—C38	1.516 (5)
C10—H10B	0.9600	C33—C34	1.375 (5)
C10—H10C	0.9600	C33—H33	0.9300
C11—C16	1.400 (6)	C34—C35	1.365 (6)
C11—C12	1.410 (6)	C34—C39	1.518 (6)
C12—C13	1.380 (7)	C35—C36	1.388 (6)
C12—C18	1.512 (7)	C35—H35	0.9300
C13—C14	1.383 (8)	C36—C37	1.514 (6)
C13—H13	0.9300	C37—H37A	0.9600
C14—C15	1.379 (8)	C37—H37B	0.9600
C14—C19	1.533 (8)	C37—H37C	0.9600
C15—C16	1.391 (7)	C38—H38A	0.9600
C15—H15	0.9300	C38—H38B	0.9600
C16—C17	1.508 (6)	C38—H38C	0.9600
C17—H17A	0.9600	C39—H39A	0.9600
C17—H17B	0.9600	C39—H39B	0.9600
C17—H17C	0.9600	C39—H39C	0.9600
C18—H18A	0.9600	S55—O55	1.497 (3)
C18—H18B	0.9600	S55—C55	1.758 (5)
C18—H18C	0.9600	S55—C56	1.766 (5)
C19—H19A	0.9600	C55—H55A	0.9600
C19—H19B	0.9600	C55—H55B	0.9600
C19—H19C	0.9600	C55—H55C	0.9600
S21—C21	1.690 (4)	C56—H56A	0.9600
N21—C21	1.312 (4)	C56—H56B	0.9600
N21—H21A	0.8600	C56—H56C	0.9600
N21—H21B	0.8600
C1—N1—H1A	120.0	C24—N24—C23	110.7 (2)
C1—N1—H1B	120.0	C5—N24—C23	112.0 (3)
H1A—N1—H1B	120.0	N21—C21—N22	117.7 (3)
C1—N2—N3	120.3 (3)	N21—C21—S21	124.6 (3)
C1—N2—H2	119.9	N22—C21—S21	117.7 (3)
N3—N2—H2	119.9	N23—C22—C26	118.5 (3)
C2—N3—N2	117.1 (3)	N23—C22—C23	126.6 (3)
C4—N4—C25	109.6 (3)	C26—C22—C23	114.9 (3)
C4—N4—C3	111.5 (2)	N24—C23—C22	115.8 (3)
C25—N4—C3	112.2 (3)	N24—C23—H23A	108.3
N1—C1—N2	115.0 (3)	C22—C23—H23A	108.3
N1—C1—S1	125.5 (3)	N24—C23—H23B	108.3
N2—C1—S1	119.5 (3)	C22—C23—H23B	108.3
N3—C2—C6	117.5 (3)	H23A—C23—H23B	107.4
N3—C2—C3	125.5 (3)	N24—C24—C25	109.7 (2)
C6—C2—C3	116.9 (3)	N24—C24—H24A	109.7
N4—C3—C2	114.2 (3)	C25—C24—H24A	109.7
N4—C3—H3A	108.7	N24—C24—H24B	109.7
C2—C3—H3A	108.7	C25—C24—H24B	109.7
N4—C3—H3B	108.7	H24A—C24—H24B	108.2
C2—C3—H3B	108.7	N4—C25—C24	110.6 (3)
H3A—C3—H3B	107.6	N4—C25—H25A	109.5
N4—C4—C5	110.5 (3)	C24—C25—H25A	109.5
N4—C4—H4A	109.6	N4—C25—H25B	109.5
C5—C4—H4A	109.6	C24—C25—H25B	109.5
N4—C4—H4B	109.6	H25A—C25—H25B	108.1
C5—C4—H4B	109.6	C22—C26—C27	121.1 (3)
H4A—C4—H4B	108.1	C22—C26—C29	117.8 (3)
N24—C5—C4	110.8 (3)	C27—C26—C29	87.6 (3)
N24—C5—H5A	109.5	C22—C26—H26	109.5
C4—C5—H5A	109.5	C27—C26—H26	109.5
N24—C5—H5B	109.5	C29—C26—H26	109.5
C4—C5—H5B	109.5	C26—C27—C28	90.2 (3)
H5A—C5—H5B	108.1	C26—C27—H27A	113.6
C2—C6—C7	120.6 (3)	C28—C27—H27A	113.6
C2—C6—C9	119.1 (3)	C26—C27—H27B	113.6
C7—C6—C9	88.0 (3)	C28—C27—H27B	113.6
C2—C6—H6	109.1	H27A—C27—H27B	110.9
C7—C6—H6	109.1	C26—C29—C28	89.2 (3)
C9—C6—H6	109.1	C26—C29—H29A	113.8
C6—C7—C8	89.5 (3)	C28—C29—H29A	113.8
C6—C7—H7A	113.7	C26—C29—H29B	113.8
C8—C7—H7A	113.7	C28—C29—H29B	113.8
C6—C7—H7B	113.7	H29A—C29—H29B	111.0
C8—C7—H7B	113.7	C31—C28—C30	110.3 (3)
H7A—C7—H7B	111.0	C31—C28—C27	118.4 (3)
C11—C8—C9	117.5 (3)	C30—C28—C27	111.5 (3)
C11—C8—C10	110.1 (3)	C31—C28—C29	117.8 (3)
C9—C8—C10	111.3 (3)	C30—C28—C29	111.0 (3)
C11—C8—C7	119.0 (3)	C27—C28—C29	85.9 (3)
C9—C8—C7	86.4 (3)	C28—C30—H30A	109.5
C10—C8—C7	110.7 (3)	C28—C30—H30B	109.5
C6—C9—C8	89.5 (3)	H30A—C30—H30B	109.5
C6—C9—H9A	113.7	C28—C30—H30C	109.5
C8—C9—H9A	113.7	H30A—C30—H30C	109.5
C6—C9—H9B	113.7	H30B—C30—H30C	109.5
C8—C9—H9B	113.7	C32—C31—C36	117.5 (3)
H9A—C9—H9B	111.0	C32—C31—C28	120.7 (3)
C8—C10—H10A	109.5	C36—C31—C28	121.8 (3)
C8—C10—H10B	109.5	C33—C32—C31	119.9 (3)
H10A—C10—H10B	109.5	C33—C32—C38	116.7 (4)
C8—C10—H10C	109.5	C31—C32—C38	123.5 (4)
H10A—C10—H10C	109.5	C34—C33—C32	123.1 (4)
H10B—C10—H10C	109.5	C34—C33—H33	118.5
C16—C11—C12	119.0 (4)	C32—C33—H33	118.5
C16—C11—C8	120.2 (4)	C35—C34—C33	116.7 (4)
C12—C11—C8	120.8 (4)	C35—C34—C39	122.6 (4)
C13—C12—C11	118.6 (5)	C33—C34—C39	120.7 (4)
C13—C12—C18	117.1 (5)	C34—C35—C36	123.2 (4)
C11—C12—C18	124.3 (4)	C34—C35—H35	118.4
C12—C13—C14	123.6 (6)	C36—C35—H35	118.4
C12—C13—H13	118.2	C35—C36—C31	119.4 (4)
C14—C13—H13	118.2	C35—C36—C37	117.1 (4)
C15—C14—C13	116.6 (5)	C31—C36—C37	123.4 (4)
C15—C14—C19	120.7 (7)	C36—C37—H37A	109.5
C13—C14—C19	122.7 (7)	C36—C37—H37B	109.5
C14—C15—C16	122.7 (5)	H37A—C37—H37B	109.5
C14—C15—H15	118.6	C36—C37—H37C	109.5
C16—C15—H15	118.6	H37A—C37—H37C	109.5
C15—C16—C11	119.3 (5)	H37B—C37—H37C	109.5
C15—C16—C17	116.5 (5)	C32—C38—H38A	109.5
C11—C16—C17	124.2 (4)	C32—C38—H38B	109.5
C16—C17—H17A	109.5	H38A—C38—H38B	109.5
C16—C17—H17B	109.5	C32—C38—H38C	109.5
H17A—C17—H17B	109.5	H38A—C38—H38C	109.5
C16—C17—H17C	109.5	H38B—C38—H38C	109.5
H17A—C17—H17C	109.5	C34—C39—H39A	109.5
H17B—C17—H17C	109.5	C34—C39—H39B	109.5
C12—C18—H18A	109.5	H39A—C39—H39B	109.5
C12—C18—H18B	109.5	C34—C39—H39C	109.5
H18A—C18—H18B	109.5	H39A—C39—H39C	109.5
C12—C18—H18C	109.5	H39B—C39—H39C	109.5
H18A—C18—H18C	109.5	O55—S55—C55	106.2 (2)
H18B—C18—H18C	109.5	O55—S55—C56	105.4 (2)
C14—C19—H19A	109.5	C55—S55—C56	98.7 (2)
C14—C19—H19B	109.5	S55—C55—H55A	109.5
H19A—C19—H19B	109.5	S55—C55—H55B	109.5
C14—C19—H19C	109.5	H55A—C55—H55B	109.5
H19A—C19—H19C	109.5	S55—C55—H55C	109.5
H19B—C19—H19C	109.5	H55A—C55—H55C	109.5
C21—N21—H21A	120.0	H55B—C55—H55C	109.5
C21—N21—H21B	120.0	S55—C56—H56A	109.5
H21A—N21—H21B	120.0	S55—C56—H56B	109.5
C21—N22—N23	120.0 (3)	H56A—C56—H56B	109.5
C21—N22—H22	120.0	S55—C56—H56C	109.5
N23—N22—H22	120.0	H56A—C56—H56C	109.5
C22—N23—N22	116.3 (3)	H56B—C56—H56C	109.5
C24—N24—C5	109.7 (2)
C1—N2—N3—C2	177.6 (3)	C4—C5—N24—C23	−178.6 (3)
N3—N2—C1—N1	8.6 (5)	N23—N22—C21—N21	2.2 (4)
N3—N2—C1—S1	−172.4 (3)	N23—N22—C21—S21	−176.7 (2)
N2—N3—C2—C6	178.7 (3)	N22—N23—C22—C26	−178.0 (3)
N2—N3—C2—C3	2.1 (5)	N22—N23—C22—C23	1.2 (5)
C4—N4—C3—C2	176.6 (3)	C24—N24—C23—C22	−173.8 (3)
C25—N4—C3—C2	−60.1 (4)	C5—N24—C23—C22	63.3 (4)
N3—C2—C3—N4	−46.1 (5)	N23—C22—C23—N24	36.2 (5)
C6—C2—C3—N4	137.3 (3)	C26—C22—C23—N24	−144.6 (3)
C25—N4—C4—C5	57.9 (3)	C5—N24—C24—C25	−58.1 (3)
C3—N4—C4—C5	−177.3 (3)	C23—N24—C24—C25	177.7 (3)
N4—C4—C5—N24	−58.1 (4)	C4—N4—C25—C24	−58.7 (3)
N3—C2—C6—C7	13.7 (5)	C3—N4—C25—C24	176.9 (3)
C3—C2—C6—C7	−169.4 (3)	N24—C24—C25—N4	59.1 (4)
N3—C2—C6—C9	120.1 (4)	N23—C22—C26—C27	13.7 (5)
C3—C2—C6—C9	−62.9 (4)	C23—C22—C26—C27	−165.6 (3)
C2—C6—C7—C8	142.3 (3)	N23—C22—C26—C29	−91.6 (4)
C9—C6—C7—C8	19.3 (2)	C23—C22—C26—C29	89.2 (4)
C6—C7—C8—C11	−138.8 (3)	C22—C26—C27—C28	−141.7 (3)
C6—C7—C8—C9	−19.2 (2)	C29—C26—C27—C28	−20.3 (3)
C6—C7—C8—C10	92.3 (3)	C22—C26—C29—C28	144.3 (3)
C2—C6—C9—C8	−143.7 (3)	C27—C26—C29—C28	20.1 (3)
C7—C6—C9—C8	−19.5 (2)	C26—C27—C28—C31	139.5 (3)
C11—C8—C9—C6	140.0 (3)	C26—C27—C28—C30	−91.0 (3)
C10—C8—C9—C6	−91.8 (3)	C26—C27—C28—C29	20.0 (3)
C7—C8—C9—C6	19.0 (2)	C26—C29—C28—C31	−139.9 (3)
C9—C8—C11—C16	41.4 (4)	C26—C29—C28—C30	91.7 (3)
C10—C8—C11—C16	−87.4 (4)	C26—C29—C28—C27	−19.8 (2)
C7—C8—C11—C16	143.4 (3)	C30—C28—C31—C32	−88.7 (4)
C9—C8—C11—C12	−139.8 (3)	C27—C28—C31—C32	41.4 (4)
C10—C8—C11—C12	91.4 (4)	C29—C28—C31—C32	142.6 (3)
C7—C8—C11—C12	−37.9 (5)	C30—C28—C31—C36	90.2 (4)
C16—C11—C12—C13	−4.9 (6)	C27—C28—C31—C36	−139.7 (3)
C8—C11—C12—C13	176.3 (4)	C29—C28—C31—C36	−38.6 (5)
C16—C11—C12—C18	173.0 (4)	C36—C31—C32—C33	5.1 (5)
C8—C11—C12—C18	−5.8 (6)	C28—C31—C32—C33	−176.0 (3)
C11—C12—C13—C14	0.9 (7)	C36—C31—C32—C38	−174.0 (4)
C18—C12—C13—C14	−177.2 (5)	C28—C31—C32—C38	4.9 (5)
C12—C13—C14—C15	2.7 (8)	C31—C32—C33—C34	−0.2 (6)
C12—C13—C14—C19	−179.2 (5)	C38—C32—C33—C34	179.0 (4)
C13—C14—C15—C16	−2.3 (7)	C32—C33—C34—C35	−3.6 (6)
C19—C14—C15—C16	179.6 (4)	C32—C33—C34—C39	176.7 (4)
C14—C15—C16—C11	−1.7 (6)	C33—C34—C35—C36	2.4 (6)
C14—C15—C16—C17	175.7 (4)	C39—C34—C35—C36	−178.0 (4)
C12—C11—C16—C15	5.3 (5)	C34—C35—C36—C31	2.6 (6)
C8—C11—C16—C15	−175.9 (3)	C34—C35—C36—C37	−175.9 (4)
C12—C11—C16—C17	−171.8 (4)	C32—C31—C36—C35	−6.3 (5)
C8—C11—C16—C17	6.9 (5)	C28—C31—C36—C35	174.8 (3)
C21—N22—N23—C22	−176.2 (3)	C32—C31—C36—C37	172.1 (4)
C4—C5—N24—C24	58.0 (3)	C28—C31—C36—C37	−6.8 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N3	0.86	2.26	2.629 (4)	106
N1—H1B···S21^i	0.86	2.56	3.407 (4)	167
N2—H2···N4	0.86	2.14	2.747 (4)	127
N21—H21A···O55^ii	0.86	2.27	2.983 (5)	140
N21—H21A···N23	0.86	2.29	2.649 (4)	105
N21—H21B···S1^ii	0.86	2.49	3.344 (4)	172
N22—H22···N24	0.86	2.08	2.701 (4)	128
C6—H6···S21^iii	0.98	2.81	3.700 (4)	152
C24—H24A···O55^iv	0.97	2.47	3.413 (5)	163
C44A—H44B···O55	0.96	2.59	3.553 (9)	175
C55—H55B···O44A^v	0.96	2.57	3.425 (9)	149
C56—H56C···O44A^v	0.96	2.41	3.297 (9)	154

Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z; (iii) −x+1, −y, −z; (iv) −x+1/2, y−1/2, −z+1/2; (v) −x, −y+1, −z.