Crystal structure of (E)-4-{1-[2-(car-bamo-thio-yl)hydrazin-1-yl-idene]ethyl}phenyl 4-methyl-benzoate.

The asymmetric unit of the title compound, C17H17N3O2S, consists of two independent mol-ecules, A and B, with different conformations: in mol-ecule A, the dihedral angles between the central benzene ring and the pendant tolyl and carbamo-thio-ylhydrazono groups are 71.12 (9) and 5.95 (8)°, respectively. The corresponding angles in mol-ecule B are 50.56 (12) and 26.43 (11)°, respectively. Both mol-ecules feature an intra-molecular N-H⋯N hydrogen bond, which closes an S(5) ring. In the crystal, mol-ecules are linked by N-H⋯O, N-H⋯S and C-H⋯O hydrogen bonds, generating a three-dimensional network.

Related literature

For background to the biological activity of thio­semicarbazone derivatives, see: Reis et al. (2013 ▸); Fatondji et al. (2013 ▸); Sau et al. (2003 ▸); Seena et al. (2006 ▸).

Experimental

Crystal data

C17H17N3O2S

M = 327.40

Triclinic,

a = 8.068 (5) Å

b = 14.037 (5) Å

c = 15.221 (5) Å

α = 99.801 (5)°

β = 96.040 (5)°

γ = 98.533 (5)°

V = 1664.7 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 293 K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▸) T min = 0.960, T max = 0.980

25169 measured reflections

6809 independent reflections

5402 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.118

S = 0.99

6809 reflections

424 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2008 ▸); cell refinement: SAINT (Bruker, 2008 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989014026942/hb7334sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014026942/hb7334Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989014026942/hb7334Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989014026942/hb7334fig1.tif

The mol­ecular structure of the title compound, showing displacement ellipsoids drawn at 30% probability level.

Click here for additional data file.

b . DOI: 10.1107/S2056989014026942/hb7334fig2.tif

The crystal packing of the title compound viewed down b axis. H-atoms not involved in H-bonds have been excluded for clarity.

CCDC reference: 1038319

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H17N3O2S	Z = 4
Mr = 327.40	F(000) = 688
Triclinic, P1	Dx = 1.306 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.068 (5) Å	Cell parameters from 6809 reflections
b = 14.037 (5) Å	θ = 1.4–26.4°
c = 15.221 (5) Å	µ = 0.21 mm−1
α = 99.801 (5)°	T = 293 K
β = 96.040 (5)°	Block, colourless
γ = 98.533 (5)°	0.20 × 0.15 × 0.10 mm
V = 1664.7 (13) Å3

Bruker SMART APEXII CCD diffractometer	6809 independent reflections
Radiation source: fine-focus sealed tube	5402 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω and φ scans	θmax = 26.4°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
Tmin = 0.960, Tmax = 0.980	k = −17→17
25169 measured reflections	l = −19→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.055P)2 + 0.6388P] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.002
6809 reflections	Δρmax = 0.44 e Å−3
424 parameters	Δρmin = −0.43 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0180 (14)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
C1A	0.2654 (3)	0.3477 (2)	0.22085 (17)	0.0842 (8)
H1A1	0.1730	0.3830	0.2150	0.126*
H1A2	0.2578	0.2980	0.1680	0.126*
H1A3	0.3704	0.3922	0.2276	0.126*
C1B	0.2414 (5)	−0.5299 (3)	1.03242 (19)	0.1202 (12)
H1B1	0.2019	−0.5983	1.0305	0.180*
H1B2	0.1741	−0.4914	1.0675	0.180*
H1B3	0.3575	−0.5132	1.0593	0.180*
C2A	0.2576 (2)	0.30002 (16)	0.30253 (13)	0.0568 (5)
C2B	0.2266 (3)	−0.50911 (19)	0.93750 (15)	0.0756 (7)
C3A	0.3217 (3)	0.21517 (16)	0.30697 (13)	0.0602 (5)
H3A	0.3704	0.1865	0.2586	0.072*
C3B	0.1513 (4)	−0.58023 (18)	0.86641 (17)	0.0840 (8)
H3B	0.1081	−0.6420	0.8766	0.101*
C4A	0.3152 (2)	0.17175 (15)	0.38156 (12)	0.0524 (4)
H4A	0.3582	0.1140	0.3828	0.063*
C4B	0.1374 (3)	−0.56294 (16)	0.77975 (15)	0.0722 (6)
H4B	0.0837	−0.6124	0.7324	0.087*
C5A	0.2449 (2)	0.21369 (13)	0.45461 (11)	0.0432 (4)
C5B	0.2031 (2)	−0.47226 (14)	0.76322 (12)	0.0510 (4)
C6A	0.1808 (3)	0.29922 (14)	0.45138 (13)	0.0538 (5)
H6A	0.1333	0.3283	0.5000	0.065*
C6B	0.2807 (3)	−0.40036 (16)	0.83396 (14)	0.0653 (6)
H6B	0.3265	−0.3391	0.8237	0.078*
C7A	0.1873 (3)	0.34158 (15)	0.37588 (15)	0.0619 (5)
H7A	0.1437	0.3991	0.3744	0.074*
C7B	0.2913 (4)	−0.41833 (19)	0.92051 (15)	0.0806 (7)
H7B	0.3429	−0.3685	0.9682	0.097*
C8A	0.2332 (2)	0.17051 (13)	0.53614 (12)	0.0463 (4)
C8B	0.1894 (3)	−0.45931 (14)	0.66842 (13)	0.0526 (4)
C9A	0.2862 (2)	0.03688 (12)	0.60304 (11)	0.0458 (4)
C9B	0.2889 (2)	−0.35490 (14)	0.57185 (12)	0.0491 (4)
C10A	0.1370 (3)	−0.01089 (14)	0.62106 (12)	0.0533 (5)
H10A	0.0367	−0.0128	0.5840	0.064*
C10B	0.3512 (3)	−0.41679 (17)	0.50947 (14)	0.0652 (6)
H10B	0.3822	−0.4744	0.5230	0.078*
C11A	0.1362 (2)	−0.05646 (13)	0.69479 (12)	0.0482 (4)
H11A	0.0345	−0.0888	0.7071	0.058*
C11B	0.3679 (3)	−0.39335 (16)	0.42609 (14)	0.0607 (5)
H11B	0.4132	−0.4348	0.3842	0.073*
C12A	0.2847 (2)	−0.05474 (11)	0.75085 (10)	0.0382 (3)
C12B	0.3183 (2)	−0.30912 (13)	0.40365 (11)	0.0436 (4)
C13A	0.4345 (2)	−0.00642 (13)	0.72968 (11)	0.0457 (4)
H13A	0.5356	−0.0044	0.7660	0.055*
C13B	0.2575 (3)	−0.24762 (14)	0.46904 (13)	0.0542 (5)
H13B	0.2255	−0.1900	0.4561	0.065*
C14A	0.4361 (2)	0.03851 (13)	0.65589 (12)	0.0492 (4)
H14A	0.5374	0.0696	0.6420	0.059*
C14B	0.2433 (3)	−0.26986 (15)	0.55296 (13)	0.0571 (5)
H14B	0.2031	−0.2274	0.5963	0.069*
C15A	0.2819 (2)	−0.10194 (12)	0.83068 (10)	0.0396 (4)
C15B	0.3277 (2)	−0.28611 (13)	0.31284 (11)	0.0445 (4)
C16A	0.1160 (2)	−0.15187 (19)	0.84955 (14)	0.0677 (6)
H16A	0.1354	−0.1916	0.8938	0.102*
H16B	0.0556	−0.1926	0.7951	0.102*
H16C	0.0506	−0.1034	0.8718	0.102*
C16B	0.4547 (3)	−0.32317 (18)	0.25743 (14)	0.0677 (6)
H16D	0.4031	−0.3458	0.1962	0.102*
H16E	0.4948	−0.3763	0.2805	0.102*
H16F	0.5479	−0.2712	0.2599	0.102*
C17A	0.5770 (2)	−0.14183 (12)	1.00110 (10)	0.0393 (4)
C17B	0.0977 (2)	−0.16131 (13)	0.17673 (11)	0.0435 (4)
N1A	0.42539 (17)	−0.09698 (10)	0.87810 (9)	0.0409 (3)
N1B	0.22145 (18)	−0.23287 (11)	0.28867 (10)	0.0463 (3)
N2A	0.42746 (19)	−0.13852 (11)	0.95384 (9)	0.0447 (3)
N2B	0.22622 (18)	−0.20308 (12)	0.20702 (10)	0.0484 (4)
H2B	0.3087	−0.2110	0.1765	0.058*
N3A	0.71545 (19)	−0.10356 (13)	0.97208 (11)	0.0579 (4)
H3A1	0.7082	−0.0778	0.9247	0.070*
H3A2	0.8130	−0.1043	1.0005	0.070*
N3B	−0.03094 (19)	−0.15950 (12)	0.22271 (10)	0.0539 (4)
H3B1	−0.0310	−0.1845	0.2705	0.065*
H3B2	−0.1152	−0.1333	0.2051	0.065*
O1A	0.1798 (2)	0.20548 (11)	0.60231 (9)	0.0701 (4)
O1B	0.1080 (2)	−0.51644 (13)	0.60607 (10)	0.0786 (5)
O2A	0.29057 (18)	0.08334 (9)	0.52831 (8)	0.0545 (3)
O2B	0.27954 (19)	−0.37271 (10)	0.65930 (8)	0.0604 (4)
S1A	0.58069 (6)	−0.19659 (4)	1.09103 (3)	0.05114 (15)
S1B	0.10592 (6)	−0.11364 (5)	0.08234 (4)	0.06621 (18)
H2A	0.340 (3)	−0.1537 (15)	0.9779 (13)	0.054 (6)*

	U11	U22	U33	U12	U13	U23
C1A	0.0860 (17)	0.1031 (19)	0.0727 (15)	0.0020 (14)	0.0047 (13)	0.0580 (14)
C1B	0.164 (3)	0.142 (3)	0.0603 (16)	0.014 (3)	0.0099 (18)	0.0494 (18)
C2A	0.0477 (10)	0.0717 (12)	0.0541 (11)	−0.0003 (9)	−0.0006 (9)	0.0336 (10)
C2B	0.0962 (18)	0.0885 (16)	0.0474 (12)	0.0142 (14)	0.0099 (11)	0.0288 (11)
C3A	0.0628 (12)	0.0775 (13)	0.0464 (10)	0.0130 (10)	0.0130 (9)	0.0244 (10)
C3B	0.121 (2)	0.0648 (14)	0.0683 (15)	−0.0018 (14)	0.0186 (15)	0.0302 (12)
C4A	0.0574 (11)	0.0596 (11)	0.0474 (10)	0.0178 (9)	0.0098 (8)	0.0219 (8)
C4B	0.0984 (18)	0.0589 (12)	0.0547 (12)	−0.0026 (12)	0.0111 (12)	0.0112 (10)
C5A	0.0419 (9)	0.0502 (9)	0.0393 (9)	0.0065 (7)	0.0013 (7)	0.0171 (7)
C5B	0.0548 (11)	0.0576 (11)	0.0451 (10)	0.0137 (9)	0.0096 (8)	0.0173 (8)
C6A	0.0566 (11)	0.0566 (11)	0.0528 (11)	0.0133 (9)	0.0079 (9)	0.0196 (9)
C6B	0.0821 (15)	0.0571 (11)	0.0556 (12)	0.0014 (11)	0.0076 (11)	0.0180 (9)
C7A	0.0600 (12)	0.0589 (11)	0.0740 (14)	0.0127 (10)	0.0019 (10)	0.0343 (10)
C7B	0.105 (2)	0.0794 (16)	0.0478 (12)	−0.0046 (14)	−0.0020 (12)	0.0091 (11)
C8A	0.0498 (10)	0.0516 (10)	0.0393 (9)	0.0082 (8)	0.0027 (8)	0.0156 (7)
C8B	0.0569 (11)	0.0562 (11)	0.0465 (10)	0.0126 (9)	0.0063 (9)	0.0125 (9)
C9A	0.0638 (11)	0.0450 (9)	0.0325 (8)	0.0151 (8)	0.0046 (8)	0.0141 (7)
C9B	0.0497 (10)	0.0621 (11)	0.0392 (9)	0.0107 (8)	0.0034 (8)	0.0204 (8)
C10A	0.0545 (11)	0.0632 (11)	0.0424 (10)	0.0086 (9)	−0.0082 (8)	0.0204 (8)
C10B	0.0807 (15)	0.0749 (13)	0.0616 (12)	0.0418 (12)	0.0230 (11)	0.0395 (11)
C11A	0.0460 (10)	0.0565 (10)	0.0426 (9)	0.0053 (8)	−0.0018 (8)	0.0182 (8)
C11B	0.0759 (14)	0.0702 (12)	0.0534 (11)	0.0376 (11)	0.0235 (10)	0.0298 (10)
C12A	0.0453 (9)	0.0385 (8)	0.0313 (8)	0.0099 (7)	0.0017 (7)	0.0078 (6)
C12B	0.0397 (9)	0.0512 (9)	0.0430 (9)	0.0083 (7)	0.0022 (7)	0.0190 (7)
C13A	0.0441 (9)	0.0533 (10)	0.0411 (9)	0.0086 (8)	0.0000 (7)	0.0164 (7)
C13B	0.0663 (12)	0.0508 (10)	0.0517 (11)	0.0187 (9)	0.0061 (9)	0.0205 (8)
C14A	0.0528 (11)	0.0536 (10)	0.0446 (10)	0.0075 (8)	0.0083 (8)	0.0189 (8)
C14B	0.0742 (13)	0.0561 (11)	0.0438 (10)	0.0170 (10)	0.0097 (9)	0.0110 (8)
C15A	0.0407 (9)	0.0462 (9)	0.0325 (8)	0.0075 (7)	0.0022 (7)	0.0106 (7)
C15B	0.0409 (9)	0.0515 (9)	0.0442 (9)	0.0069 (7)	0.0030 (7)	0.0204 (8)
C16A	0.0453 (11)	0.1051 (17)	0.0563 (12)	−0.0030 (11)	−0.0034 (9)	0.0447 (12)
C16B	0.0735 (14)	0.0900 (15)	0.0585 (12)	0.0372 (12)	0.0215 (11)	0.0388 (11)
C17A	0.0379 (8)	0.0475 (9)	0.0350 (8)	0.0091 (7)	0.0028 (7)	0.0138 (7)
C17B	0.0372 (9)	0.0533 (9)	0.0430 (9)	0.0068 (7)	0.0027 (7)	0.0200 (7)
N1A	0.0416 (8)	0.0509 (8)	0.0341 (7)	0.0096 (6)	0.0029 (6)	0.0186 (6)
N1B	0.0410 (8)	0.0596 (9)	0.0423 (8)	0.0074 (7)	0.0019 (6)	0.0241 (7)
N2A	0.0367 (8)	0.0647 (9)	0.0380 (7)	0.0081 (7)	0.0036 (6)	0.0257 (7)
N2B	0.0385 (8)	0.0706 (10)	0.0449 (8)	0.0136 (7)	0.0073 (6)	0.0307 (7)
N3A	0.0373 (8)	0.0918 (12)	0.0540 (9)	0.0095 (8)	0.0052 (7)	0.0417 (9)
N3B	0.0493 (9)	0.0763 (11)	0.0493 (9)	0.0240 (8)	0.0136 (7)	0.0326 (8)
O1A	0.1059 (12)	0.0702 (9)	0.0497 (8)	0.0356 (9)	0.0302 (8)	0.0248 (7)
O1B	0.0948 (12)	0.0818 (10)	0.0504 (9)	−0.0068 (9)	0.0023 (8)	0.0117 (8)
O2A	0.0786 (9)	0.0569 (7)	0.0376 (6)	0.0248 (7)	0.0118 (6)	0.0216 (6)
O2B	0.0743 (9)	0.0671 (8)	0.0420 (7)	0.0061 (7)	0.0067 (6)	0.0227 (6)
S1A	0.0424 (2)	0.0724 (3)	0.0461 (3)	0.0105 (2)	0.00270 (19)	0.0335 (2)
S1B	0.0452 (3)	0.1100 (5)	0.0638 (3)	0.0247 (3)	0.0145 (2)	0.0588 (3)

C1A—C2A	1.511 (3)	C10A—H10A	0.9300
C1A—H1A1	0.9600	C10B—C11B	1.379 (3)
C1A—H1A2	0.9600	C10B—H10B	0.9300
C1A—H1A3	0.9600	C11A—C12A	1.390 (2)
C1B—C2B	1.518 (3)	C11A—H11A	0.9300
C1B—H1B1	0.9600	C11B—C12B	1.387 (3)
C1B—H1B2	0.9600	C11B—H11B	0.9300
C1B—H1B3	0.9600	C12A—C13A	1.392 (2)
C2A—C3A	1.376 (3)	C12A—C15A	1.480 (2)
C2A—C7A	1.385 (3)	C12B—C13B	1.383 (3)
C2B—C3B	1.360 (4)	C12B—C15B	1.479 (2)
C2B—C7B	1.381 (3)	C13A—C14A	1.379 (2)
C3A—C4A	1.379 (2)	C13A—H13A	0.9300
C3A—H3A	0.9300	C13B—C14B	1.378 (3)
C3B—C4B	1.377 (3)	C13B—H13B	0.9300
C3B—H3B	0.9300	C14A—H14A	0.9300
C4A—C5A	1.383 (3)	C14B—H14B	0.9300
C4A—H4A	0.9300	C15A—N1A	1.284 (2)
C4B—C5B	1.379 (3)	C15A—C16A	1.496 (3)
C4B—H4B	0.9300	C15B—N1B	1.283 (2)
C5A—C6A	1.382 (3)	C15B—C16B	1.490 (3)
C5A—C8A	1.476 (2)	C16A—H16A	0.9600
C5B—C6B	1.368 (3)	C16A—H16B	0.9600
C5B—C8B	1.480 (3)	C16A—H16C	0.9600
C6A—C7A	1.383 (3)	C16B—H16D	0.9600
C6A—H6A	0.9300	C16B—H16E	0.9600
C6B—C7B	1.379 (3)	C16B—H16F	0.9600
C6B—H6B	0.9300	C17A—N3A	1.318 (2)
C7A—H7A	0.9300	C17A—N2A	1.350 (2)
C7B—H7B	0.9300	C17A—S1A	1.6798 (16)
C8A—O1A	1.195 (2)	C17B—N3B	1.312 (2)
C8A—O2A	1.362 (2)	C17B—N2B	1.343 (2)
C8B—O1B	1.195 (2)	C17B—S1B	1.6883 (17)
C8B—O2B	1.357 (2)	N1A—N2A	1.3774 (18)
C9A—C10A	1.366 (3)	N1B—N2B	1.3795 (19)
C9A—C14A	1.375 (3)	N2A—H2A	0.85 (2)
C9A—O2A	1.4053 (19)	N2B—H2B	0.8600
C9B—C10B	1.363 (3)	N3A—H3A1	0.8600
C9B—C14B	1.367 (3)	N3A—H3A2	0.8600
C9B—O2B	1.403 (2)	N3B—H3B1	0.8600
C10A—C11A	1.383 (2)	N3B—H3B2	0.8600
C2A—C1A—H1A1	109.5	C11B—C10B—H10B	120.3
C2A—C1A—H1A2	109.5	C10A—C11A—C12A	121.17 (17)
H1A1—C1A—H1A2	109.5	C10A—C11A—H11A	119.4
C2A—C1A—H1A3	109.5	C12A—C11A—H11A	119.4
H1A1—C1A—H1A3	109.5	C10B—C11B—C12B	121.18 (19)
H1A2—C1A—H1A3	109.5	C10B—C11B—H11B	119.4
C2B—C1B—H1B1	109.5	C12B—C11B—H11B	119.4
C2B—C1B—H1B2	109.5	C11A—C12A—C13A	117.70 (15)
H1B1—C1B—H1B2	109.5	C11A—C12A—C15A	120.75 (15)
C2B—C1B—H1B3	109.5	C13A—C12A—C15A	121.55 (14)
H1B1—C1B—H1B3	109.5	C13B—C12B—C11B	117.59 (16)
H1B2—C1B—H1B3	109.5	C13B—C12B—C15B	120.94 (15)
C3A—C2A—C7A	118.00 (17)	C11B—C12B—C15B	121.47 (17)
C3A—C2A—C1A	121.3 (2)	C14A—C13A—C12A	121.33 (16)
C7A—C2A—C1A	120.7 (2)	C14A—C13A—H13A	119.3
C3B—C2B—C7B	118.1 (2)	C12A—C13A—H13A	119.3
C3B—C2B—C1B	120.7 (2)	C14B—C13B—C12B	121.41 (17)
C7B—C2B—C1B	121.2 (2)	C14B—C13B—H13B	119.3
C2A—C3A—C4A	121.4 (2)	C12B—C13B—H13B	119.3
C2A—C3A—H3A	119.3	C9A—C14A—C13A	119.26 (17)
C4A—C3A—H3A	119.3	C9A—C14A—H14A	120.4
C2B—C3B—C4B	121.6 (2)	C13A—C14A—H14A	120.4
C2B—C3B—H3B	119.2	C9B—C14B—C13B	119.39 (18)
C4B—C3B—H3B	119.2	C9B—C14B—H14B	120.3
C3A—C4A—C5A	120.29 (18)	C13B—C14B—H14B	120.3
C3A—C4A—H4A	119.9	N1A—C15A—C12A	116.24 (14)
C5A—C4A—H4A	119.9	N1A—C15A—C16A	125.21 (15)
C3B—C4B—C5B	120.0 (2)	C12A—C15A—C16A	118.55 (14)
C3B—C4B—H4B	120.0	N1B—C15B—C12B	114.65 (16)
C5B—C4B—H4B	120.0	N1B—C15B—C16B	125.04 (16)
C6A—C5A—C4A	118.99 (16)	C12B—C15B—C16B	120.30 (15)
C6A—C5A—C8A	118.13 (16)	C15A—C16A—H16A	109.5
C4A—C5A—C8A	122.88 (16)	C15A—C16A—H16B	109.5
C6B—C5B—C4B	119.00 (18)	H16A—C16A—H16B	109.5
C6B—C5B—C8B	123.52 (18)	C15A—C16A—H16C	109.5
C4B—C5B—C8B	117.45 (18)	H16A—C16A—H16C	109.5
C5A—C6A—C7A	120.05 (19)	H16B—C16A—H16C	109.5
C5A—C6A—H6A	120.0	C15B—C16B—H16D	109.5
C7A—C6A—H6A	120.0	C15B—C16B—H16E	109.5
C5B—C6B—C7B	120.3 (2)	H16D—C16B—H16E	109.5
C5B—C6B—H6B	119.9	C15B—C16B—H16F	109.5
C7B—C6B—H6B	119.9	H16D—C16B—H16F	109.5
C6A—C7A—C2A	121.27 (19)	H16E—C16B—H16F	109.5
C6A—C7A—H7A	119.4	N3A—C17A—N2A	117.40 (15)
C2A—C7A—H7A	119.4	N3A—C17A—S1A	122.89 (13)
C6B—C7B—C2B	121.0 (2)	N2A—C17A—S1A	119.68 (13)
C6B—C7B—H7B	119.5	N3B—C17B—N2B	117.76 (15)
C2B—C7B—H7B	119.5	N3B—C17B—S1B	122.49 (13)
O1A—C8A—O2A	122.20 (16)	N2B—C17B—S1B	119.75 (13)
O1A—C8A—C5A	125.62 (17)	C15A—N1A—N2A	117.89 (14)
O2A—C8A—C5A	112.18 (15)	C15B—N1B—N2B	119.05 (15)
O1B—C8B—O2B	122.65 (18)	C17A—N2A—N1A	119.45 (14)
O1B—C8B—C5B	125.32 (18)	C17A—N2A—H2A	116.6 (14)
O2B—C8B—C5B	112.02 (16)	N1A—N2A—H2A	123.1 (14)
C10A—C9A—C14A	121.03 (16)	C17B—N2B—N1B	117.74 (14)
C10A—C9A—O2A	120.61 (16)	C17B—N2B—H2B	121.1
C14A—C9A—O2A	118.34 (16)	N1B—N2B—H2B	121.1
C10B—C9B—C14B	120.89 (17)	C17A—N3A—H3A1	120.0
C10B—C9B—O2B	121.41 (17)	C17A—N3A—H3A2	120.0
C14B—C9B—O2B	117.57 (17)	H3A1—N3A—H3A2	120.0
C9A—C10A—C11A	119.48 (17)	C17B—N3B—H3B1	120.0
C9A—C10A—H10A	120.3	C17B—N3B—H3B2	120.0
C11A—C10A—H10A	120.3	H3B1—N3B—H3B2	120.0
C9B—C10B—C11B	119.50 (18)	C8A—O2A—C9A	116.43 (13)
C9B—C10B—H10B	120.3	C8B—O2B—C9B	117.77 (15)
C7A—C2A—C3A—C4A	0.7 (3)	C10B—C11B—C12B—C15B	−176.86 (19)
C1A—C2A—C3A—C4A	179.79 (19)	C11A—C12A—C13A—C14A	0.2 (3)
C7B—C2B—C3B—C4B	−0.7 (5)	C15A—C12A—C13A—C14A	−179.16 (16)
C1B—C2B—C3B—C4B	−179.7 (3)	C11B—C12B—C13B—C14B	−1.3 (3)
C2A—C3A—C4A—C5A	−0.7 (3)	C15B—C12B—C13B—C14B	178.00 (18)
C2B—C3B—C4B—C5B	1.0 (4)	C10A—C9A—C14A—C13A	−1.9 (3)
C3A—C4A—C5A—C6A	0.3 (3)	O2A—C9A—C14A—C13A	179.83 (15)
C3A—C4A—C5A—C8A	179.62 (17)	C12A—C13A—C14A—C9A	1.1 (3)
C3B—C4B—C5B—C6B	−0.4 (4)	C10B—C9B—C14B—C13B	1.3 (3)
C3B—C4B—C5B—C8B	177.9 (2)	O2B—C9B—C14B—C13B	177.27 (17)
C4A—C5A—C6A—C7A	0.1 (3)	C12B—C13B—C14B—C9B	−0.6 (3)
C8A—C5A—C6A—C7A	−179.26 (17)	C11A—C12A—C15A—N1A	179.65 (16)
C4B—C5B—C6B—C7B	−0.6 (4)	C13A—C12A—C15A—N1A	−1.0 (2)
C8B—C5B—C6B—C7B	−178.8 (2)	C11A—C12A—C15A—C16A	0.2 (3)
C5A—C6A—C7A—C2A	−0.1 (3)	C13A—C12A—C15A—C16A	179.55 (18)
C3A—C2A—C7A—C6A	−0.3 (3)	C13B—C12B—C15B—N1B	−26.1 (2)
C1A—C2A—C7A—C6A	−179.40 (19)	C11B—C12B—C15B—N1B	153.15 (19)
C5B—C6B—C7B—C2B	1.0 (4)	C13B—C12B—C15B—C16B	153.3 (2)
C3B—C2B—C7B—C6B	−0.3 (4)	C11B—C12B—C15B—C16B	−27.4 (3)
C1B—C2B—C7B—C6B	178.7 (3)	C12A—C15A—N1A—N2A	178.84 (14)
C6A—C5A—C8A—O1A	−3.7 (3)	C16A—C15A—N1A—N2A	−1.8 (3)
C4A—C5A—C8A—O1A	177.0 (2)	C12B—C15B—N1B—N2B	176.61 (14)
C6A—C5A—C8A—O2A	175.97 (16)	C16B—C15B—N1B—N2B	−2.8 (3)
C4A—C5A—C8A—O2A	−3.4 (2)	N3A—C17A—N2A—N1A	0.6 (2)
C6B—C5B—C8B—O1B	−171.8 (2)	S1A—C17A—N2A—N1A	−177.45 (12)
C4B—C5B—C8B—O1B	9.9 (3)	C15A—N1A—N2A—C17A	174.57 (16)
C6B—C5B—C8B—O2B	7.3 (3)	N3B—C17B—N2B—N1B	−5.9 (2)
C4B—C5B—C8B—O2B	−170.9 (2)	S1B—C17B—N2B—N1B	174.13 (12)
C14A—C9A—C10A—C11A	1.5 (3)	C15B—N1B—N2B—C17B	169.44 (17)
O2A—C9A—C10A—C11A	179.68 (16)	O1A—C8A—O2A—C9A	−0.9 (3)
C14B—C9B—C10B—C11B	−0.2 (3)	C5A—C8A—O2A—C9A	179.38 (14)
O2B—C9B—C10B—C11B	−176.00 (19)	C10A—C9A—O2A—C8A	75.9 (2)
C9A—C10A—C11A—C12A	−0.2 (3)	C14A—C9A—O2A—C8A	−105.8 (2)
C9B—C10B—C11B—C12B	−1.7 (3)	O1B—C8B—O2B—C9B	−6.1 (3)
C10A—C11A—C12A—C13A	−0.6 (3)	C5B—C8B—O2B—C9B	174.76 (16)
C10A—C11A—C12A—C15A	178.70 (17)	C10B—C9B—O2B—C8B	−57.6 (3)
C10B—C11B—C12B—C13B	2.4 (3)	C14B—C9B—O2B—C8B	126.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3A1···N1A	0.86	2.28	2.634 (3)	105
N3B—H3B1···N1B	0.86	2.25	2.600 (3)	105
N2A—H2A···S1Bi	0.85 (2)	2.66 (2)	3.432 (3)	153.5 (8)
N2B—H2B···S1Aii	0.86	2.67	3.513 (3)	169
N3A—H3A2···S1Biii	0.86	2.58	3.444 (3)	178
N3B—H3B1···O1Aiv	0.86	2.42	3.159 (3)	145
N3B—N3B2···S1Av	0.86	2.78	3.456 (3)	136
C6A—H6A···O1Bvi	0.93	2.53	3.354 (3)	148

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N3AH3A1N1A	0.86	2.28	2.634(3)	105
N3BH3B1N1B	0.86	2.25	2.600(3)	105
N2AH2AS1B i	0.85(2)	2.66(2)	3.432(3)	153.5(8)
N2BH2BS1A ii	0.86	2.67	3.513(3)	169
N3AH3A2S1B iii	0.86	2.58	3.444(3)	178
N3BH3B1O1A iv	0.86	2.42	3.159(3)	145
N3BN3B2S1A v	0.86	2.78	3.456(3)	136
C6AH6AO1B vi	0.93	2.53	3.354(3)	148

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .