4-Morpholin­yl{2-[1-(2-pyridin­yl)ethyl­idene]diazan-2-iumyl­idene}methane­thiol­ate

The title compound, C₁₂H₁₆N₄OS, is zwitterionic and exists in the EZ configuration of thio­semicarbazones. The thio­carbon­yl S atom and coordinating pyrid­yl N atom are aligned cis to each other, avoiding the possibility of a structural reorientation upon coordination. Two crystallographically independent mol­ecules, A and B, are observed in the asymmetric unit, with the morphol­yl ring adopting a chair conformation in both mol­ecules. N—H...N and N—H...S intra­molecular hydrogen bonds are observed in the mol­ecular structure, generating four rings of motif R₁²(5). There is zigzag packing in the unit cell, involving both intra- and inter­molecular hydrogen-bonding inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.044
• wR factor = 0.125
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.64 mm
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         22

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

4-morpholinyl{2-[1-(2-pyridinyl)ethylidene]diazan-2-iumylidene}methanethiolate

Crystal data

C12H16N4OS	F(000) = 1120
Mr = 264.35	Dx = 1.323 Mg m^−3
Monoclinic, P21/c	Melting point: 461 K K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.158 (9) Å	Cell parameters from 14456 reflections
b = 11.075 (7) Å	θ = 2.2–26.5°
c = 17.877 (1) Å	µ = 0.24 mm^−1
β = 108.776 (1)°	T = 293 K
V = 2654 (2) Å^3	Rod, yellow
Z = 8	0.64 × 0.44 × 0.40 mm

Data collection

Siemens SMART CCD area-detector diffractometer	5503 independent reflections
Radiation source: fine-focus sealed tube	4012 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 8.33 pixels mm^-1	θmax = 26.5°, θmin = 2.2°
ω scans	h = −12→17
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
Tmin = 0.882, Tmax = 0.909	l = −22→22
14456 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0543P)^2 + 1.0486P] where P = (Fo^2 + 2Fc^2)/3
5503 reflections	(Δ/σ)max = 0.001
335 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.21 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
S1A	0.39687 (4)	0.26810 (5)	0.20884 (3)	0.04550 (16)
O1A	0.10742 (14)	0.0876 (2)	0.28912 (13)	0.0934 (7)
N1A	0.29837 (13)	0.17134 (18)	0.29958 (11)	0.0508 (5)
N2A	0.45951 (12)	0.11157 (15)	0.33232 (9)	0.0407 (4)
N3A	0.54316 (12)	0.11623 (15)	0.31170 (10)	0.0387 (4)
N4A	0.68515 (14)	0.1335 (2)	0.24724 (11)	0.0577 (5)
C1A	0.28327 (19)	0.0916 (3)	0.35979 (15)	0.0692 (8)
H1AA	0.2753	0.1394	0.4028	0.083*
H1AB	0.3411	0.0400	0.3809	0.083*
C2A	0.1933 (2)	0.0165 (3)	0.32480 (19)	0.0820 (9)
H2AB	0.2046	−0.0368	0.2854	0.098*
H2AC	0.1820	−0.0332	0.3657	0.098*
C3A	0.1231 (2)	0.1599 (3)	0.22851 (18)	0.0861 (10)
H3AB	0.0638	0.2076	0.2037	0.103*
H3AC	0.1343	0.1080	0.1885	0.103*
C4A	0.20991 (18)	0.2417 (2)	0.26005 (16)	0.0629 (7)
H4AB	0.2204	0.2875	0.2172	0.075*
H4AC	0.1969	0.2982	0.2970	0.075*
C5A	0.38544 (15)	0.17921 (18)	0.28386 (11)	0.0384 (4)
C6A	0.62836 (15)	0.06946 (18)	0.35242 (11)	0.0411 (5)
C7A	0.70958 (15)	0.08118 (19)	0.31852 (12)	0.0447 (5)
C8A	0.75752 (19)	0.1475 (3)	0.21519 (16)	0.0703 (8)
H8AA	0.7414	0.1844	0.1659	0.084*
C9A	0.85421 (19)	0.1109 (3)	0.25048 (18)	0.0710 (8)
H9AA	0.9021	0.1231	0.2258	0.085*
C10A	0.87865 (18)	0.0562 (2)	0.32266 (19)	0.0690 (8)
H10A	0.9434	0.0295	0.3478	0.083*
C11A	0.80535 (17)	0.0409 (2)	0.35791 (15)	0.0571 (6)
H11A	0.8202	0.0043	0.4072	0.069*
C12A	0.63955 (18)	0.0109 (2)	0.42936 (13)	0.0557 (6)
H12A	0.5780	0.0174	0.4409	0.084*
H12B	0.6918	0.0502	0.4702	0.084*
H12C	0.6561	−0.0727	0.4268	0.084*
S1B	0.90197 (4)	0.30078 (6)	0.06077 (4)	0.05760 (19)
O1B	1.17114 (13)	0.1265 (2)	−0.04934 (12)	0.0842 (6)
N1B	0.98901 (13)	0.21700 (19)	−0.04151 (11)	0.0550 (5)
N2B	0.82661 (12)	0.16472 (16)	−0.07177 (10)	0.0420 (4)
N3B	0.74437 (12)	0.17228 (16)	−0.04903 (10)	0.0393 (4)
N4B	0.60177 (13)	0.20605 (18)	0.01424 (11)	0.0512 (5)
C1B	0.99540 (18)	0.1563 (3)	−0.11241 (14)	0.0615 (7)
H1BA	1.0055	0.2157	−0.1490	0.074*
H1BB	0.9335	0.1141	−0.1383	0.074*
C2B	1.0795 (2)	0.0691 (3)	−0.09086 (18)	0.0743 (8)
H2BB	1.0661	0.0058	−0.0581	0.089*
H2BC	1.0849	0.0320	−0.1385	0.089*
C3B	1.1634 (2)	0.1789 (4)	0.02070 (19)	0.0902 (10)
H3BB	1.2266	0.2158	0.0500	0.108*
H3BC	1.1495	0.1161	0.0535	0.108*
C4B	1.08381 (18)	0.2710 (3)	0.00372 (18)	0.0721 (8)
H4BB	1.0793	0.3035	0.0529	0.087*
H4BC	1.0995	0.3369	−0.0261	0.087*
C5B	0.90503 (15)	0.22363 (19)	−0.02149 (12)	0.0427 (5)
C6B	0.65781 (15)	0.12941 (18)	−0.08907 (12)	0.0398 (5)
C7B	0.57717 (15)	0.14549 (19)	−0.05456 (12)	0.0410 (5)
C8B	0.53107 (19)	0.2214 (3)	0.04734 (15)	0.0625 (7)
H8BA	0.5475	0.2628	0.0951	0.075*
C9B	0.43502 (19)	0.1797 (3)	0.01510 (16)	0.0645 (7)
H9BA	0.3880	0.1930	0.0405	0.077*
C10B	0.40996 (17)	0.1186 (2)	−0.05488 (15)	0.0592 (7)
H10B	0.3454	0.0897	−0.0780	0.071*
C11B	0.48176 (16)	0.1000 (2)	−0.09114 (14)	0.0503 (5)
H11B	0.4666	0.0582	−0.1387	0.060*
C12B	0.64354 (17)	0.0688 (2)	−0.16558 (13)	0.0556 (6)
H12D	0.6976	0.0894	−0.1847	0.083*
H12E	0.5816	0.0946	−0.2031	0.083*
H12F	0.6422	−0.0171	−0.1587	0.083*
H2N3	0.7519 (16)	0.209 (2)	−0.0052 (13)	0.045 (6)*
H1N3	0.5405 (17)	0.155 (2)	0.2671 (14)	0.056 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1A	0.0454 (3)	0.0494 (3)	0.0426 (3)	−0.0008 (2)	0.0155 (2)	0.0101 (2)
O1A	0.0485 (11)	0.137 (2)	0.0982 (15)	−0.0127 (12)	0.0285 (10)	0.0398 (14)
N1A	0.0380 (10)	0.0641 (12)	0.0514 (10)	0.0004 (9)	0.0161 (8)	0.0168 (9)
N2A	0.0395 (9)	0.0448 (10)	0.0380 (9)	−0.0007 (7)	0.0130 (7)	0.0035 (7)
N3A	0.0390 (9)	0.0400 (10)	0.0360 (9)	−0.0020 (7)	0.0106 (7)	−0.0011 (7)
N4A	0.0429 (11)	0.0801 (15)	0.0512 (11)	0.0004 (10)	0.0163 (9)	0.0021 (10)
C1A	0.0554 (15)	0.094 (2)	0.0632 (15)	−0.0014 (14)	0.0266 (12)	0.0300 (15)
C2A	0.076 (2)	0.091 (2)	0.091 (2)	−0.0123 (17)	0.0432 (17)	0.0271 (18)
C3A	0.0453 (15)	0.129 (3)	0.0785 (19)	−0.0063 (16)	0.0116 (14)	0.0319 (19)
C4A	0.0474 (14)	0.0714 (17)	0.0744 (17)	0.0120 (12)	0.0260 (12)	0.0203 (14)
C5A	0.0401 (11)	0.0382 (11)	0.0363 (10)	−0.0045 (8)	0.0114 (8)	−0.0026 (8)
C6A	0.0434 (11)	0.0359 (11)	0.0402 (11)	0.0008 (9)	0.0083 (9)	−0.0050 (8)
C7A	0.0395 (11)	0.0421 (12)	0.0487 (12)	0.0003 (9)	0.0089 (9)	−0.0100 (10)
C8A	0.0541 (16)	0.100 (2)	0.0628 (16)	−0.0060 (14)	0.0268 (13)	−0.0076 (15)
C9A	0.0468 (15)	0.086 (2)	0.086 (2)	−0.0115 (13)	0.0300 (14)	−0.0316 (17)
C10A	0.0389 (13)	0.0660 (17)	0.097 (2)	0.0043 (12)	0.0145 (14)	−0.0237 (16)
C11A	0.0446 (13)	0.0509 (14)	0.0681 (15)	0.0049 (11)	0.0074 (11)	−0.0073 (11)
C12A	0.0607 (15)	0.0535 (14)	0.0485 (13)	0.0083 (11)	0.0116 (11)	0.0062 (11)
S1B	0.0470 (3)	0.0720 (4)	0.0531 (3)	0.0014 (3)	0.0152 (3)	−0.0234 (3)
O1B	0.0459 (10)	0.1226 (18)	0.0907 (14)	0.0138 (11)	0.0314 (10)	−0.0125 (13)
N1B	0.0356 (10)	0.0696 (13)	0.0604 (11)	−0.0012 (9)	0.0162 (9)	−0.0232 (10)
N2B	0.0357 (9)	0.0478 (10)	0.0439 (9)	0.0011 (8)	0.0147 (7)	−0.0067 (8)
N3B	0.0375 (9)	0.0419 (10)	0.0396 (9)	0.0036 (7)	0.0138 (8)	−0.0022 (8)
N4B	0.0456 (11)	0.0600 (12)	0.0514 (11)	0.0024 (9)	0.0203 (9)	−0.0020 (9)
C1B	0.0488 (14)	0.0805 (18)	0.0597 (14)	0.0007 (12)	0.0239 (12)	−0.0164 (13)
C2B	0.0740 (19)	0.0750 (19)	0.0874 (19)	0.0105 (15)	0.0449 (16)	−0.0100 (16)
C3B	0.0415 (15)	0.144 (3)	0.082 (2)	0.0048 (17)	0.0163 (14)	−0.020 (2)
C4B	0.0448 (14)	0.088 (2)	0.0853 (19)	−0.0174 (13)	0.0239 (13)	−0.0310 (16)
C5B	0.0392 (11)	0.0434 (12)	0.0449 (11)	0.0071 (9)	0.0127 (9)	−0.0016 (9)
C6B	0.0381 (11)	0.0366 (11)	0.0425 (11)	0.0033 (9)	0.0100 (9)	0.0028 (9)
C7B	0.0386 (11)	0.0397 (11)	0.0447 (11)	0.0061 (9)	0.0132 (9)	0.0101 (9)
C8B	0.0579 (15)	0.0782 (18)	0.0595 (14)	0.0086 (13)	0.0300 (12)	−0.0010 (13)
C9B	0.0491 (14)	0.0791 (19)	0.0754 (18)	0.0148 (13)	0.0340 (13)	0.0197 (15)
C10B	0.0380 (12)	0.0686 (17)	0.0702 (16)	0.0040 (11)	0.0161 (11)	0.0246 (13)
C11B	0.0410 (12)	0.0531 (14)	0.0533 (13)	0.0019 (10)	0.0104 (10)	0.0137 (10)
C12B	0.0495 (13)	0.0619 (15)	0.0534 (13)	−0.0002 (11)	0.0140 (11)	−0.0149 (11)

Geometric parameters (Å, º)

S1A—C5A	1.713 (2)	S1B—C5B	1.713 (2)
O1A—C2A	1.416 (4)	O1B—C3B	1.416 (3)
O1A—C3A	1.422 (3)	O1B—C2B	1.421 (3)
N1A—C5A	1.353 (3)	N1B—C5B	1.350 (3)
N1A—C4A	1.451 (3)	N1B—C4B	1.454 (3)
N1A—C1A	1.460 (3)	N1B—C1B	1.463 (3)
N2A—N3A	1.350 (2)	N2B—C5B	1.350 (3)
N2A—C5A	1.352 (2)	N2B—N3B	1.354 (2)
N3A—C6A	1.299 (2)	N3B—C6B	1.294 (3)
N3A—H1N3	0.90 (2)	N3B—H2N3	0.86 (2)
N4A—C8A	1.334 (3)	N4B—C8B	1.328 (3)
N4A—C7A	1.340 (3)	N4B—C7B	1.345 (3)
C1A—C2A	1.480 (4)	C1B—C2B	1.484 (4)
C1A—H1AA	0.9700	C1B—H1BA	0.9700
C1A—H1AB	0.9700	C1B—H1BB	0.9700
C2A—H2AB	0.9700	C2B—H2BB	0.9700
C2A—H2AC	0.9700	C2B—H2BC	0.9700
C3A—C4A	1.484 (4)	C3B—C4B	1.477 (4)
C3A—H3AB	0.9700	C3B—H3BB	0.9700
C3A—H3AC	0.9700	C3B—H3BC	0.9700
C4A—H4AB	0.9700	C4B—H4BB	0.9700
C4A—H4AC	0.9700	C4B—H4BC	0.9700
C6A—C7A	1.468 (3)	C6B—C7B	1.473 (3)
C6A—C12A	1.482 (3)	C6B—C12B	1.478 (3)
C7A—C11A	1.385 (3)	C7B—C11B	1.392 (3)
C8A—C9A	1.371 (4)	C8B—C9B	1.375 (4)
C8A—H8AA	0.9300	C8B—H8BA	0.9300
C9A—C10A	1.366 (4)	C9B—C10B	1.365 (4)
C9A—H9AA	0.9300	C9B—H9BA	0.9300
C10A—C11A	1.387 (4)	C10B—C11B	1.386 (3)
C10A—H10A	0.9300	C10B—H10B	0.9300
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—H12A	0.9600	C12B—H12D	0.9600
C12A—H12B	0.9600	C12B—H12E	0.9600
C12A—H12C	0.9600	C12B—H12F	0.9600
C2A—O1A—C3A	109.5 (2)	C3B—O1B—C2B	109.1 (2)
C5A—N1A—C4A	124.46 (18)	C5B—N1B—C4B	124.36 (19)
C5A—N1A—C1A	123.48 (19)	C5B—N1B—C1B	124.07 (19)
C4A—N1A—C1A	112.06 (18)	C4B—N1B—C1B	111.56 (18)
N3A—N2A—C5A	111.83 (16)	C5B—N2B—N3B	111.87 (16)
C6A—N3A—N2A	124.73 (18)	C6B—N3B—N2B	124.35 (18)
C6A—N3A—H1N3	117.1 (15)	C6B—N3B—H2N3	119.7 (15)
N2A—N3A—H1N3	118.1 (15)	N2B—N3B—H2N3	115.9 (15)
C8A—N4A—C7A	117.4 (2)	C8B—N4B—C7B	117.5 (2)
N1A—C1A—C2A	109.8 (2)	N1B—C1B—C2B	110.0 (2)
N1A—C1A—H1AA	109.7	N1B—C1B—H1BA	109.7
C2A—C1A—H1AA	109.7	C2B—C1B—H1BA	109.7
N1A—C1A—H1AB	109.7	N1B—C1B—H1BB	109.7
C2A—C1A—H1AB	109.7	C2B—C1B—H1BB	109.7
H1AA—C1A—H1AB	108.2	H1BA—C1B—H1BB	108.2
O1A—C2A—C1A	112.1 (3)	O1B—C2B—C1B	111.5 (2)
O1A—C2A—H2AB	109.2	O1B—C2B—H2BB	109.3
C1A—C2A—H2AB	109.2	C1B—C2B—H2BB	109.3
O1A—C2A—H2AC	109.2	O1B—C2B—H2BC	109.3
C1A—C2A—H2AC	109.2	C1B—C2B—H2BC	109.3
H2AB—C2A—H2AC	107.9	H2BB—C2B—H2BC	108.0
O1A—C3A—C4A	111.6 (2)	O1B—C3B—C4B	111.9 (3)
O1A—C3A—H3AB	109.3	O1B—C3B—H3BB	109.2
C4A—C3A—H3AB	109.3	C4B—C3B—H3BB	109.2
O1A—C3A—H3AC	109.3	O1B—C3B—H3BC	109.2
C4A—C3A—H3AC	109.3	C4B—C3B—H3BC	109.2
H3AB—C3A—H3AC	108.0	H3BB—C3B—H3BC	107.9
N1A—C4A—C3A	109.7 (2)	N1B—C4B—C3B	109.6 (2)
N1A—C4A—H4AB	109.7	N1B—C4B—H4BB	109.7
C3A—C4A—H4AB	109.7	C3B—C4B—H4BB	109.7
N1A—C4A—H4AC	109.7	N1B—C4B—H4BC	109.7
C3A—C4A—H4AC	109.7	C3B—C4B—H4BC	109.7
H4AB—C4A—H4AC	108.2	H4BB—C4B—H4BC	108.2
N2A—C5A—N1A	113.72 (17)	N1B—C5B—N2B	113.76 (18)
N2A—C5A—S1A	124.82 (15)	N1B—C5B—S1B	121.51 (16)
N1A—C5A—S1A	121.46 (15)	N2B—C5B—S1B	124.73 (15)
N3A—C6A—C7A	116.28 (18)	N3B—C6B—C7B	116.60 (18)
N3A—C6A—C12A	119.80 (19)	N3B—C6B—C12B	120.09 (19)
C7A—C6A—C12A	123.90 (19)	C7B—C6B—C12B	123.31 (19)
N4A—C7A—C11A	122.2 (2)	N4B—C7B—C11B	122.5 (2)
N4A—C7A—C6A	115.72 (18)	N4B—C7B—C6B	115.85 (18)
C11A—C7A—C6A	122.0 (2)	C11B—C7B—C6B	121.7 (2)
N4A—C8A—C9A	124.0 (3)	N4B—C8B—C9B	123.8 (2)
N4A—C8A—H8AA	118.0	N4B—C8B—H8BA	118.1
C9A—C8A—H8AA	118.0	C9B—C8B—H8BA	118.1
C10A—C9A—C8A	118.5 (3)	C10B—C9B—C8B	118.8 (2)
C10A—C9A—H9AA	120.7	C10B—C9B—H9BA	120.6
C8A—C9A—H9AA	120.7	C8B—C9B—H9BA	120.6
C9A—C10A—C11A	119.0 (2)	C9B—C10B—C11B	119.3 (2)
C9A—C10A—H10A	120.5	C9B—C10B—H10B	120.4
C11A—C10A—H10A	120.5	C11B—C10B—H10B	120.4
C7A—C11A—C10A	118.9 (2)	C10B—C11B—C7B	118.3 (2)
C7A—C11A—H11A	120.6	C10B—C11B—H11B	120.9
C10A—C11A—H11A	120.6	C7B—C11B—H11B	120.9
C6A—C12A—H12A	109.5	C6B—C12B—H12D	109.5
C6A—C12A—H12B	109.5	C6B—C12B—H12E	109.5
H12A—C12A—H12B	109.5	H12D—C12B—H12E	109.5
C6A—C12A—H12C	109.5	C6B—C12B—H12F	109.5
H12A—C12A—H12C	109.5	H12D—C12B—H12F	109.5
H12B—C12A—H12C	109.5	H12E—C12B—H12F	109.5
C5A—N2A—N3A—C6A	173.01 (18)	C5B—N2B—N3B—C6B	176.05 (19)
C5A—N1A—C1A—C2A	−127.6 (3)	C5B—N1B—C1B—C2B	−127.7 (3)
C4A—N1A—C1A—C2A	53.3 (3)	C4B—N1B—C1B—C2B	53.3 (3)
C3A—O1A—C2A—C1A	59.4 (3)	C3B—O1B—C2B—C1B	59.9 (3)
N1A—C1A—C2A—O1A	−56.1 (3)	N1B—C1B—C2B—O1B	−56.5 (3)
C2A—O1A—C3A—C4A	−59.8 (4)	C2B—O1B—C3B—C4B	−60.8 (4)
C5A—N1A—C4A—C3A	127.1 (3)	C5B—N1B—C4B—C3B	127.4 (3)
C1A—N1A—C4A—C3A	−53.8 (3)	C1B—N1B—C4B—C3B	−53.7 (3)
O1A—C3A—C4A—N1A	57.1 (3)	O1B—C3B—C4B—N1B	57.8 (4)
N3A—N2A—C5A—N1A	176.28 (17)	C4B—N1B—C5B—N2B	−178.9 (2)
N3A—N2A—C5A—S1A	−3.8 (2)	C1B—N1B—C5B—N2B	2.3 (3)
C4A—N1A—C5A—N2A	175.2 (2)	C4B—N1B—C5B—S1B	1.1 (3)
C1A—N1A—C5A—N2A	−3.7 (3)	C1B—N1B—C5B—S1B	−177.71 (19)
C4A—N1A—C5A—S1A	−4.7 (3)	N3B—N2B—C5B—N1B	179.20 (18)
C1A—N1A—C5A—S1A	176.34 (19)	N3B—N2B—C5B—S1B	−0.8 (3)
N2A—N3A—C6A—C7A	178.18 (17)	N2B—N3B—C6B—C7B	179.57 (17)
N2A—N3A—C6A—C12A	−3.1 (3)	N2B—N3B—C6B—C12B	−0.9 (3)
C8A—N4A—C7A—C11A	−1.0 (4)	C8B—N4B—C7B—C11B	0.2 (3)
C8A—N4A—C7A—C6A	178.9 (2)	C8B—N4B—C7B—C6B	−179.5 (2)
N3A—C6A—C7A—N4A	−3.3 (3)	N3B—C6B—C7B—N4B	1.6 (3)
C12A—C6A—C7A—N4A	178.0 (2)	C12B—C6B—C7B—N4B	−177.9 (2)
N3A—C6A—C7A—C11A	176.54 (19)	N3B—C6B—C7B—C11B	−178.06 (19)
C12A—C6A—C7A—C11A	−2.1 (3)	C12B—C6B—C7B—C11B	2.4 (3)
C7A—N4A—C8A—C9A	0.6 (4)	C7B—N4B—C8B—C9B	−0.4 (4)
N4A—C8A—C9A—C10A	0.3 (4)	N4B—C8B—C9B—C10B	0.2 (4)
C8A—C9A—C10A—C11A	−0.7 (4)	C8B—C9B—C10B—C11B	0.2 (4)
N4A—C7A—C11A—C10A	0.6 (3)	C9B—C10B—C11B—C7B	−0.4 (3)
C6A—C7A—C11A—C10A	−179.3 (2)	N4B—C7B—C11B—C10B	0.2 (3)
C9A—C10A—C11A—C7A	0.3 (4)	C6B—C7B—C11B—C10B	179.85 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H1N3···S1A	0.90 (2)	2.33 (2)	2.837 (2)	116 (2)
N3A—H1N3···N4A	0.90 (2)	2.20 (3)	2.626 (3)	109 (2)
N3B—H2N3···S1B	0.86 (2)	2.31 (2)	2.835 (2)	120 (2)
N3B—H2N3···N4B	0.86 (2)	2.26 (2)	2.639 (3)	106 (2)
C1A—H1AB···N2A	0.97	2.27	2.703 (3)	106
C2A—H2AC···S1B^i	0.97	2.74	3.673 (3)	161
C4A—H4AB···S1A	0.97	2.56	3.081 (3)	114
C1B—H1BB···N2B	0.97	2.28	2.714 (3)	106
C12A—H12A···N2A	0.96	2.36	2.811 (3)	108
C12B—H12D···N2B	0.96	2.39	2.804 (3)	105
C4B—H4BB···S1B	0.97	2.56	3.077 (3)	113

Symmetry code: (i) −x+1, y−1/2, −z+1/2.