Olanzapinium dipicrate.

THE ASYMMETRIC UNIT OF THE TITLE SALT [SYSTEMATIC NAME: 2-methyl-4-(4-methyl-piperazin-4-ium-1-yl)-10H-thieno[2,3-b][1,5]benzodiazepinium bis-(2,4,6-trinitro-phenolate)], C(17)H(22)N(4)S(2+)·2C(6)H(2)N(3)O(7) (-), consists of a diprotonated olanzapinium cation and two independent picrate anions. In the cation, the piperazine ring adopts a distorted chair conformation and contains a positively charged N atom with quaternary character and the N atom in the seven-membered 1,5-diazepine ring, which adopts a boat configuration, is also protonated. The dihedral angle between the benzene and thiene rings flanking the diazepine ring is 58.8 (1)°. In one of the picrate anions, a nitro group is disordered over two sets of sites in a 0.748 (5):0.252 (5) ratio, and the benzene ring has a flat envelope conformation with the O(-) C atom displaced from the mean plane of the other five C atoms [maximum deviation 0.0151 (14) Å] by 0.1449 (14) Å. In the crystal, N-H⋯O hydrogen bonds and weak inter-molecular C-H⋯S and C-H⋯O inter-actions link the components, forming a three-dimensional network.

Related literature

For the use of olanzapine in the management of bipolar disorder, see: Narasimhan et al. (2007 ▶) and for toxicity and fatality associated with its overdose, see: Chue & Singer (2003 ▶). For related structures, see: Capuano et al. (2003 ▶); Wawrzycka-Gorczyca et al. (2004a ▶,b ▶, 2006 ▶); Ravikumar et al. (2005 ▶); Thakuria & Nangia (2011a ▶,b ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H22N4S2+·2C6H2N3O7 −

M = 770.66

Orthorhombic,

a = 22.1660 (4) Å

b = 12.7349 (2) Å

c = 23.3951 (4) Å

V = 6604.04 (19) Å3

Z = 8

Cu Kα radiation

μ = 1.65 mm−1

T = 173 K

0.28 × 0.22 × 0.12 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.702, T max = 1.000

44193 measured reflections

6524 independent reflections

5508 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.107

S = 1.03

6524 reflections

506 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813000640/bv2217sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000640/bv2217Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813000640/bv2217Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H22N4S2+·2C6H2N3O7−	F(000) = 3184
Mr = 770.66	Dx = 1.550 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 14060 reflections
a = 22.1660 (4) Å	θ = 3.5–72.4°
b = 12.7349 (2) Å	µ = 1.65 mm−1
c = 23.3951 (4) Å	T = 173 K
V = 6604.04 (19) Å3	Chunk, orange
Z = 8	0.28 × 0.22 × 0.12 mm

Agilent Xcalibur (Eos, Gemini) diffractometer	6524 independent reflections
Radiation source: Enhance (Cu) X-ray Source	5508 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
Detector resolution: 16.0416 pixels mm-1	θmax = 72.5°, θmin = 3.8°
ω scans	h = −27→18
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −15→15
Tmin = 0.702, Tmax = 1.000	l = −28→28
44193 measured reflections

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0538P)2 + 2.5536P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
6524 reflections	Δρmax = 0.29 e Å−3
506 parameters	Δρmin = −0.25 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: 0.00018 (3)

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 > 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.579266 (18)	0.92049 (4)	0.563737 (17)	0.04414 (11)
N1	0.53681 (6)	0.91960 (11)	0.67285 (5)	0.0387 (3)
H1	0.5726 (9)	0.9405 (16)	0.6797 (8)	0.051 (5)*
N2	0.41626 (6)	0.85066 (10)	0.67800 (5)	0.0348 (3)
H2	0.3945 (7)	0.8196 (13)	0.7041 (7)	0.031 (4)*
N3	0.40406 (5)	0.70712 (10)	0.61938 (5)	0.0331 (3)
N4	0.38127 (6)	0.48631 (11)	0.63699 (5)	0.0367 (3)
H4	0.3563 (8)	0.4761 (15)	0.6057 (8)	0.051 (5)*
C1	0.53417 (8)	0.86715 (13)	0.51046 (6)	0.0405 (4)
C2	0.48250 (7)	0.82924 (12)	0.53276 (6)	0.0360 (3)
H2A	0.4522	0.7992	0.5106	0.043*
C3	0.47835 (6)	0.83939 (12)	0.59394 (6)	0.0327 (3)
C4	0.52808 (7)	0.88977 (12)	0.61615 (6)	0.0347 (3)
C5	0.49176 (7)	0.98865 (13)	0.69407 (6)	0.0375 (3)
C6	0.50589 (9)	1.08776 (14)	0.71524 (7)	0.0472 (4)
H6	0.5456	1.1114	0.7148	0.057*
C7	0.46052 (11)	1.15108 (15)	0.73700 (8)	0.0585 (5)
H7	0.4701	1.2161	0.7526	0.070*
C8	0.40162 (11)	1.11827 (15)	0.73559 (9)	0.0603 (5)
H8	0.3714	1.1618	0.7496	0.072*
C9	0.38688 (9)	1.02055 (14)	0.71346 (7)	0.0487 (4)
H9	0.3468	0.9988	0.7123	0.058*
C10	0.43210 (7)	0.95562 (12)	0.69310 (6)	0.0372 (3)
C11	0.43149 (6)	0.79801 (12)	0.63109 (6)	0.0310 (3)
C12	0.34715 (6)	0.67087 (13)	0.64582 (6)	0.0368 (3)
H12A	0.3165	0.6636	0.6164	0.044*
H12B	0.3333	0.7231	0.6730	0.044*
C13	0.35504 (7)	0.56706 (14)	0.67612 (6)	0.0410 (4)
H13A	0.3814	0.5764	0.7088	0.049*
H13B	0.3162	0.5429	0.6900	0.049*
C14	0.43908 (6)	0.52558 (13)	0.61187 (6)	0.0346 (3)
H14A	0.4551	0.4736	0.5856	0.042*
H14B	0.4684	0.5360	0.6421	0.042*
C15	0.42908 (6)	0.62748 (12)	0.58063 (6)	0.0320 (3)
H15A	0.4671	0.6523	0.5651	0.038*
H15B	0.4015	0.6162	0.5491	0.038*
C16	0.39062 (9)	0.38329 (15)	0.66601 (8)	0.0541 (5)
H16A	0.4068	0.3337	0.6392	0.081*
H16B	0.3528	0.3579	0.6804	0.081*
H16C	0.4184	0.3920	0.6972	0.081*
C17	0.55665 (9)	0.86961 (16)	0.45003 (7)	0.0536 (5)
H17A	0.5706	0.9390	0.4410	0.080*
H17B	0.5245	0.8508	0.4245	0.080*
H17C	0.5892	0.8206	0.4458	0.080*
O1A	0.35350 (6)	0.77573 (10)	0.76857 (5)	0.0494 (3)
O2AA	0.24618 (11)	0.8297 (2)	0.72987 (8)	0.0643 (7)	0.748 (5)
O2AB	0.2333 (4)	0.7808 (8)	0.7354 (3)	0.0643 (7)	0.252 (5)
O3A	0.17093 (6)	0.82511 (12)	0.79120 (5)	0.0590 (4)
O4A	0.20275 (6)	0.83164 (10)	0.98965 (5)	0.0481 (3)
O5A	0.29258 (7)	0.83455 (13)	1.02399 (5)	0.0632 (4)
O6A	0.46450 (6)	0.80267 (14)	0.90134 (6)	0.0729 (4)
O7A	0.45449 (6)	0.86082 (14)	0.81632 (6)	0.0703 (4)
N1A	0.22493 (7)	0.81934 (12)	0.77957 (6)	0.0451 (3)
N2A	0.25736 (7)	0.83171 (10)	0.98370 (5)	0.0385 (3)
N3A	0.43342 (7)	0.82737 (12)	0.86039 (6)	0.0463 (3)
C1A	0.33162 (7)	0.80385 (11)	0.81504 (6)	0.0349 (3)
C2A	0.26786 (7)	0.81740 (11)	0.82648 (6)	0.0335 (3)
C3A	0.24387 (7)	0.82569 (11)	0.88050 (6)	0.0322 (3)
H3A	0.2023	0.8300	0.8857	0.039*
C4A	0.28246 (7)	0.82754 (11)	0.92697 (6)	0.0326 (3)
C5A	0.34468 (7)	0.82687 (11)	0.91966 (6)	0.0355 (3)
H5A	0.3702	0.8311	0.9512	0.043*
C6A	0.36793 (7)	0.82002 (12)	0.86602 (6)	0.0359 (3)
O1B	0.35005 (5)	0.40692 (10)	0.53601 (5)	0.0439 (3)
O2B	0.43648 (6)	0.46565 (12)	0.45828 (6)	0.0636 (4)
O3B	0.42526 (6)	0.35698 (12)	0.38873 (6)	0.0590 (4)
O4B	0.23268 (6)	0.43743 (10)	0.29528 (5)	0.0495 (3)
O5B	0.15172 (5)	0.44113 (10)	0.34730 (5)	0.0509 (3)
O6B	0.16618 (6)	0.40258 (13)	0.54990 (6)	0.0642 (4)
O7B	0.24767 (6)	0.45166 (13)	0.59228 (5)	0.0607 (4)
N1B	0.40510 (6)	0.41103 (11)	0.42742 (6)	0.0404 (3)
N2B	0.20709 (6)	0.43498 (10)	0.34187 (6)	0.0389 (3)
N3B	0.21983 (6)	0.42506 (11)	0.54935 (6)	0.0423 (3)
C1B	0.31671 (7)	0.41479 (11)	0.49376 (6)	0.0327 (3)
C2B	0.33981 (7)	0.41348 (11)	0.43547 (6)	0.0328 (3)
C3B	0.30566 (7)	0.41716 (10)	0.38727 (6)	0.0323 (3)
H3B	0.3236	0.4144	0.3514	0.039*
C4B	0.24333 (7)	0.42513 (11)	0.39268 (6)	0.0323 (3)
C5B	0.21633 (7)	0.42567 (11)	0.44617 (7)	0.0331 (3)
H5B	0.1745	0.4287	0.4493	0.040*
C6B	0.25131 (7)	0.42169 (11)	0.49451 (6)	0.0328 (3)

	U11	U22	U33	U12	U13	U23
S1	0.0416 (2)	0.0577 (2)	0.03319 (19)	−0.01666 (18)	0.00612 (15)	−0.00591 (17)
N1	0.0354 (7)	0.0518 (8)	0.0288 (6)	−0.0032 (6)	−0.0028 (5)	−0.0044 (6)
N2	0.0365 (6)	0.0401 (7)	0.0279 (6)	−0.0006 (5)	0.0053 (5)	−0.0001 (5)
N3	0.0261 (6)	0.0449 (7)	0.0284 (6)	−0.0014 (5)	0.0050 (5)	−0.0049 (5)
N4	0.0336 (6)	0.0504 (7)	0.0261 (6)	−0.0097 (6)	0.0026 (5)	0.0029 (5)
C1	0.0472 (9)	0.0447 (8)	0.0296 (7)	−0.0103 (7)	0.0022 (6)	−0.0017 (6)
C2	0.0404 (8)	0.0406 (8)	0.0269 (7)	−0.0048 (6)	−0.0004 (6)	−0.0003 (6)
C3	0.0322 (7)	0.0381 (7)	0.0278 (7)	0.0014 (6)	0.0003 (6)	−0.0004 (6)
C4	0.0352 (7)	0.0415 (8)	0.0275 (7)	−0.0009 (6)	0.0013 (6)	0.0007 (6)
C5	0.0479 (9)	0.0413 (8)	0.0232 (7)	0.0005 (7)	−0.0022 (6)	0.0017 (6)
C6	0.0662 (11)	0.0441 (9)	0.0312 (8)	−0.0058 (8)	−0.0053 (8)	0.0003 (7)
C7	0.0919 (15)	0.0391 (9)	0.0446 (10)	0.0011 (9)	−0.0001 (10)	−0.0036 (8)
C8	0.0820 (14)	0.0447 (10)	0.0541 (11)	0.0180 (10)	0.0118 (10)	−0.0040 (8)
C9	0.0531 (10)	0.0491 (10)	0.0438 (9)	0.0109 (8)	0.0071 (8)	−0.0005 (8)
C10	0.0465 (8)	0.0386 (8)	0.0264 (7)	0.0045 (7)	0.0019 (6)	0.0002 (6)
C11	0.0271 (6)	0.0403 (8)	0.0256 (6)	0.0047 (6)	−0.0017 (5)	0.0009 (6)
C12	0.0237 (6)	0.0583 (9)	0.0284 (7)	−0.0046 (6)	0.0028 (5)	−0.0101 (7)
C13	0.0333 (7)	0.0660 (10)	0.0238 (7)	−0.0108 (7)	0.0051 (6)	−0.0042 (7)
C14	0.0276 (7)	0.0458 (8)	0.0304 (7)	−0.0043 (6)	0.0031 (6)	−0.0002 (6)
C15	0.0272 (6)	0.0424 (8)	0.0264 (7)	−0.0025 (6)	0.0054 (5)	−0.0033 (6)
C16	0.0580 (11)	0.0583 (11)	0.0458 (10)	−0.0085 (9)	0.0077 (8)	0.0159 (8)
C17	0.0638 (11)	0.0657 (11)	0.0314 (8)	−0.0231 (9)	0.0097 (8)	−0.0027 (8)
O1A	0.0613 (7)	0.0564 (7)	0.0306 (6)	−0.0125 (6)	0.0103 (5)	−0.0060 (5)
O2AA	0.0631 (12)	0.106 (2)	0.0235 (7)	0.0052 (13)	−0.0053 (7)	0.0046 (10)
O2AB	0.0631 (12)	0.106 (2)	0.0235 (7)	0.0052 (13)	−0.0053 (7)	0.0046 (10)
O3A	0.0481 (7)	0.0840 (10)	0.0447 (7)	−0.0176 (7)	−0.0127 (6)	0.0023 (6)
O4A	0.0556 (7)	0.0495 (7)	0.0391 (6)	−0.0013 (5)	0.0091 (5)	0.0018 (5)
O5A	0.0711 (9)	0.0933 (11)	0.0253 (6)	−0.0010 (8)	−0.0083 (6)	0.0001 (6)
O6A	0.0511 (8)	0.1067 (12)	0.0609 (9)	0.0217 (8)	−0.0123 (7)	0.0111 (8)
O7A	0.0458 (7)	0.1042 (12)	0.0608 (9)	−0.0024 (8)	0.0038 (6)	0.0181 (8)
N1A	0.0582 (9)	0.0472 (8)	0.0299 (7)	−0.0005 (7)	−0.0116 (6)	−0.0024 (6)
N2A	0.0566 (8)	0.0317 (6)	0.0271 (6)	0.0002 (6)	−0.0013 (6)	0.0008 (5)
N3A	0.0446 (8)	0.0480 (8)	0.0464 (8)	0.0113 (6)	−0.0022 (6)	−0.0015 (6)
C1A	0.0499 (9)	0.0279 (7)	0.0270 (7)	−0.0042 (6)	0.0019 (6)	0.0008 (5)
C2A	0.0473 (8)	0.0275 (7)	0.0259 (7)	−0.0025 (6)	−0.0068 (6)	0.0017 (5)
C3A	0.0431 (8)	0.0228 (6)	0.0308 (7)	−0.0015 (6)	−0.0028 (6)	0.0010 (5)
C4A	0.0494 (8)	0.0231 (6)	0.0251 (7)	0.0008 (6)	−0.0019 (6)	0.0009 (5)
C5A	0.0483 (8)	0.0288 (7)	0.0294 (7)	0.0067 (6)	−0.0087 (6)	0.0000 (6)
C6A	0.0422 (8)	0.0304 (7)	0.0349 (8)	0.0043 (6)	−0.0022 (6)	0.0010 (6)
O1B	0.0393 (6)	0.0569 (7)	0.0357 (6)	0.0006 (5)	−0.0067 (5)	−0.0067 (5)
O2B	0.0372 (6)	0.0820 (9)	0.0716 (9)	−0.0158 (6)	0.0051 (6)	−0.0263 (8)
O3B	0.0432 (6)	0.0829 (10)	0.0509 (7)	0.0141 (6)	0.0049 (6)	−0.0162 (7)
O4B	0.0610 (7)	0.0525 (7)	0.0350 (6)	0.0002 (6)	−0.0071 (5)	−0.0003 (5)
O5B	0.0428 (6)	0.0530 (7)	0.0569 (7)	0.0108 (5)	−0.0142 (5)	−0.0093 (6)
O6B	0.0421 (7)	0.0905 (10)	0.0601 (8)	−0.0069 (7)	0.0161 (6)	0.0031 (7)
O7B	0.0554 (7)	0.0927 (10)	0.0340 (6)	0.0016 (7)	0.0070 (6)	−0.0038 (7)
N1B	0.0343 (6)	0.0458 (7)	0.0409 (7)	0.0008 (6)	0.0028 (6)	−0.0014 (6)
N2B	0.0466 (7)	0.0274 (6)	0.0426 (7)	0.0033 (5)	−0.0101 (6)	−0.0039 (5)
N3B	0.0397 (7)	0.0468 (8)	0.0405 (7)	0.0033 (6)	0.0083 (6)	0.0042 (6)
C1B	0.0346 (7)	0.0293 (7)	0.0343 (7)	−0.0022 (6)	−0.0002 (6)	−0.0027 (6)
C2B	0.0308 (7)	0.0295 (7)	0.0382 (8)	−0.0015 (6)	0.0020 (6)	−0.0019 (6)
C3B	0.0400 (8)	0.0246 (6)	0.0323 (7)	−0.0007 (6)	0.0026 (6)	−0.0013 (5)
C4B	0.0389 (7)	0.0225 (6)	0.0356 (7)	0.0001 (5)	−0.0051 (6)	−0.0007 (5)
C5B	0.0309 (7)	0.0246 (7)	0.0439 (8)	0.0007 (5)	−0.0004 (6)	−0.0008 (6)
C6B	0.0348 (7)	0.0292 (7)	0.0343 (7)	−0.0003 (6)	0.0037 (6)	0.0004 (6)

S1—C4	1.7157 (15)	C16—H16B	0.9600
S1—C1	1.7362 (16)	C16—H16C	0.9600
N1—C4	1.3935 (19)	C17—H17A	0.9600
N1—C5	1.420 (2)	C17—H17B	0.9600
N1—H1	0.852 (19)	C17—H17C	0.9600
N2—C11	1.3295 (19)	O1A—C1A	1.2432 (18)
N2—C10	1.426 (2)	O2AA—N1A	1.261 (2)
N2—H2	0.872 (17)	O2AB—N1A	1.158 (7)
N3—C11	1.336 (2)	O3A—N1A	1.230 (2)
N3—C15	1.4690 (18)	O4A—N2A	1.2184 (18)
N3—C12	1.4788 (18)	O5A—N2A	1.2244 (18)
N4—C16	1.492 (2)	O6A—N3A	1.2212 (19)
N4—C13	1.494 (2)	O7A—N3A	1.209 (2)
N4—C14	1.4958 (18)	N1A—C2A	1.4528 (19)
N4—H4	0.926 (19)	N2A—C4A	1.4401 (19)
C1—C2	1.348 (2)	N3A—C6A	1.461 (2)
C1—C17	1.499 (2)	C1A—C2A	1.449 (2)
C2—C3	1.440 (2)	C1A—C6A	1.453 (2)
C2—H2A	0.9300	C2A—C3A	1.375 (2)
C3—C4	1.377 (2)	C3A—C4A	1.384 (2)
C3—C11	1.453 (2)	C3A—H3A	0.9300
C5—C10	1.388 (2)	C4A—C5A	1.390 (2)
C5—C6	1.391 (2)	C5A—C6A	1.359 (2)
C6—C7	1.386 (3)	C5A—H5A	0.9300
C6—H6	0.9300	O1B—C1B	1.2383 (18)
C7—C8	1.371 (3)	O2B—N1B	1.2201 (19)
C7—H7	0.9300	O3B—N1B	1.2219 (18)
C8—C9	1.387 (3)	O4B—N2B	1.2291 (18)
C8—H8	0.9300	O5B—N2B	1.2363 (18)
C9—C10	1.384 (2)	O6B—N3B	1.2233 (19)
C9—H9	0.9300	O7B—N3B	1.2264 (18)
C12—C13	1.510 (2)	N1B—C2B	1.4599 (19)
C12—H12A	0.9700	N2B—C4B	1.4401 (19)
C12—H12B	0.9700	N3B—C6B	1.4613 (19)
C13—H13A	0.9700	C1B—C6B	1.452 (2)
C13—H13B	0.9700	C1B—C2B	1.457 (2)
C14—C15	1.506 (2)	C2B—C3B	1.359 (2)
C14—H14A	0.9700	C3B—C4B	1.391 (2)
C14—H14B	0.9700	C3B—H3B	0.9300
C15—H15A	0.9700	C4B—C5B	1.387 (2)
C15—H15B	0.9700	C5B—C6B	1.372 (2)
C16—H16A	0.9600	C5B—H5B	0.9300
C4—S1—C1	92.47 (7)	C14—C15—H15B	109.5
C4—N1—C5	113.83 (13)	H15A—C15—H15B	108.1
C4—N1—H1	113.2 (13)	N4—C16—H16A	109.5
C5—N1—H1	113.3 (14)	N4—C16—H16B	109.5
C11—N2—C10	127.92 (13)	H16A—C16—H16B	109.5
C11—N2—H2	119.2 (11)	N4—C16—H16C	109.5
C10—N2—H2	112.8 (11)	H16A—C16—H16C	109.5
C11—N3—C15	123.57 (12)	H16B—C16—H16C	109.5
C11—N3—C12	124.95 (12)	C1—C17—H17A	109.5
C15—N3—C12	111.39 (12)	C1—C17—H17B	109.5
C16—N4—C13	112.37 (13)	H17A—C17—H17B	109.5
C16—N4—C14	110.72 (13)	C1—C17—H17C	109.5
C13—N4—C14	110.11 (12)	H17A—C17—H17C	109.5
C16—N4—H4	108.6 (12)	H17B—C17—H17C	109.5
C13—N4—H4	110.4 (12)	O2AB—N1A—O3A	112.2 (4)
C14—N4—H4	104.4 (12)	O3A—N1A—O2AA	124.15 (16)
C2—C1—C17	130.90 (15)	O2AB—N1A—C2A	124.2 (4)
C2—C1—S1	110.58 (11)	O3A—N1A—C2A	118.11 (13)
C17—C1—S1	118.52 (12)	O2AA—N1A—C2A	116.98 (16)
C1—C2—C3	113.99 (14)	O4A—N2A—O5A	123.05 (14)
C1—C2—H2A	123.0	O4A—N2A—C4A	119.28 (13)
C3—C2—H2A	123.0	O5A—N2A—C4A	117.66 (14)
C4—C3—C2	111.45 (13)	O7A—N3A—O6A	122.79 (16)
C4—C3—C11	121.03 (13)	O7A—N3A—C6A	118.90 (14)
C2—C3—C11	127.40 (13)	O6A—N3A—C6A	118.27 (15)
C3—C4—N1	126.67 (14)	O1A—C1A—C2A	125.21 (14)
C3—C4—S1	111.47 (11)	O1A—C1A—C6A	122.84 (15)
N1—C4—S1	121.76 (12)	C2A—C1A—C6A	111.82 (13)
C10—C5—C6	119.69 (16)	C3A—C2A—C1A	123.79 (13)
C10—C5—N1	118.46 (14)	C3A—C2A—N1A	116.09 (14)
C6—C5—N1	121.85 (16)	C1A—C2A—N1A	120.09 (13)
C7—C6—C5	119.68 (18)	C2A—C3A—C4A	118.97 (14)
C7—C6—H6	120.2	C2A—C3A—H3A	120.5
C5—C6—H6	120.2	C4A—C3A—H3A	120.5
C8—C7—C6	120.31 (18)	C3A—C4A—C5A	121.11 (14)
C8—C7—H7	119.8	C3A—C4A—N2A	119.07 (14)
C6—C7—H7	119.8	C5A—C4A—N2A	119.81 (13)
C7—C8—C9	120.45 (18)	C6A—C5A—C4A	119.35 (14)
C7—C8—H8	119.8	C6A—C5A—H5A	120.3
C9—C8—H8	119.8	C4A—C5A—H5A	120.3
C10—C9—C8	119.60 (18)	C5A—C6A—C1A	123.83 (15)
C10—C9—H9	120.2	C5A—C6A—N3A	117.11 (14)
C8—C9—H9	120.2	C1A—C6A—N3A	119.05 (14)
C9—C10—C5	120.22 (16)	O2B—N1B—O3B	123.44 (14)
C9—C10—N2	117.83 (15)	O2B—N1B—C2B	118.47 (13)
C5—C10—N2	121.51 (14)	O3B—N1B—C2B	118.04 (13)
N2—C11—N3	119.39 (13)	O4B—N2B—O5B	123.21 (14)
N2—C11—C3	119.48 (14)	O4B—N2B—C4B	118.47 (13)
N3—C11—C3	121.12 (13)	O5B—N2B—C4B	118.32 (13)
N3—C12—C13	111.76 (12)	O6B—N3B—O7B	123.05 (15)
N3—C12—H12A	109.3	O6B—N3B—C6B	117.82 (14)
C13—C12—H12A	109.3	O7B—N3B—C6B	119.13 (13)
N3—C12—H12B	109.3	O1B—C1B—C6B	126.23 (14)
C13—C12—H12B	109.3	O1B—C1B—C2B	122.46 (13)
H12A—C12—H12B	107.9	C6B—C1B—C2B	111.27 (13)
N4—C13—C12	111.10 (12)	C3B—C2B—C1B	125.50 (13)
N4—C13—H13A	109.4	C3B—C2B—N1B	116.48 (13)
C12—C13—H13A	109.4	C1B—C2B—N1B	117.99 (13)
N4—C13—H13B	109.4	C2B—C3B—C4B	118.70 (14)
C12—C13—H13B	109.4	C2B—C3B—H3B	120.6
H13A—C13—H13B	108.0	C4B—C3B—H3B	120.6
N4—C14—C15	110.66 (12)	C5B—C4B—C3B	120.72 (13)
N4—C14—H14A	109.5	C5B—C4B—N2B	120.24 (14)
C15—C14—H14A	109.5	C3B—C4B—N2B	119.03 (13)
N4—C14—H14B	109.5	C6B—C5B—C4B	119.97 (14)
C15—C14—H14B	109.5	C6B—C5B—H5B	120.0
H14A—C14—H14B	108.1	C4B—C5B—H5B	120.0
N3—C15—C14	110.55 (12)	C5B—C6B—C1B	123.80 (14)
N3—C15—H15A	109.5	C5B—C6B—N3B	116.92 (13)
C14—C15—H15A	109.5	C1B—C6B—N3B	119.28 (13)
N3—C15—H15B	109.5
C4—S1—C1—C2	0.61 (14)	O3A—N1A—C2A—C3A	−2.0 (2)
C4—S1—C1—C17	−179.44 (15)	O2AA—N1A—C2A—C3A	168.4 (2)
C17—C1—C2—C3	178.40 (18)	O2AB—N1A—C2A—C1A	24.2 (6)
S1—C1—C2—C3	−1.65 (19)	O3A—N1A—C2A—C1A	176.02 (14)
C1—C2—C3—C4	2.1 (2)	O2AA—N1A—C2A—C1A	−13.6 (3)
C1—C2—C3—C11	−173.89 (15)	C1A—C2A—C3A—C4A	4.0 (2)
C2—C3—C4—N1	174.83 (15)	N1A—C2A—C3A—C4A	−178.08 (13)
C11—C3—C4—N1	−8.8 (2)	C2A—C3A—C4A—C5A	3.5 (2)
C2—C3—C4—S1	−1.61 (17)	C2A—C3A—C4A—N2A	−177.38 (12)
C11—C3—C4—S1	174.72 (11)	O4A—N2A—C4A—C3A	1.3 (2)
C5—N1—C4—C3	−58.5 (2)	O5A—N2A—C4A—C3A	−179.14 (14)
C5—N1—C4—S1	117.65 (14)	O4A—N2A—C4A—C5A	−179.57 (13)
C1—S1—C4—C3	0.61 (13)	O5A—N2A—C4A—C5A	0.0 (2)
C1—S1—C4—N1	−176.03 (14)	C3A—C4A—C5A—C6A	−2.7 (2)
C4—N1—C5—C10	58.27 (18)	N2A—C4A—C5A—C6A	178.21 (13)
C4—N1—C5—C6	−121.34 (16)	C4A—C5A—C6A—C1A	−5.7 (2)
C10—C5—C6—C7	2.3 (2)	C4A—C5A—C6A—N3A	175.64 (13)
N1—C5—C6—C7	−178.14 (15)	O1A—C1A—C6A—C5A	−164.27 (15)
C5—C6—C7—C8	−2.7 (3)	C2A—C1A—C6A—C5A	11.8 (2)
C6—C7—C8—C9	1.3 (3)	O1A—C1A—C6A—N3A	14.4 (2)
C7—C8—C9—C10	0.5 (3)	C2A—C1A—C6A—N3A	−169.53 (13)
C8—C9—C10—C5	−0.9 (2)	O7A—N3A—C6A—C5A	−152.39 (16)
C8—C9—C10—N2	171.61 (16)	O6A—N3A—C6A—C5A	25.2 (2)
C6—C5—C10—C9	−0.5 (2)	O7A—N3A—C6A—C1A	28.9 (2)
N1—C5—C10—C9	179.92 (14)	O6A—N3A—C6A—C1A	−153.59 (16)
C6—C5—C10—N2	−172.70 (14)	O1B—C1B—C2B—C3B	176.98 (14)
N1—C5—C10—N2	7.7 (2)	C6B—C1B—C2B—C3B	−0.6 (2)
C11—N2—C10—C9	133.74 (16)	O1B—C1B—C2B—N1B	−4.9 (2)
C11—N2—C10—C5	−53.9 (2)	C6B—C1B—C2B—N1B	177.57 (12)
C10—N2—C11—N3	−168.35 (14)	O2B—N1B—C2B—C3B	137.08 (16)
C10—N2—C11—C3	12.7 (2)	O3B—N1B—C2B—C3B	−40.4 (2)
C15—N3—C11—N2	−159.95 (13)	O2B—N1B—C2B—C1B	−41.2 (2)
C12—N3—C11—N2	16.3 (2)	O3B—N1B—C2B—C1B	141.27 (15)
C15—N3—C11—C3	19.0 (2)	C1B—C2B—C3B—C4B	1.5 (2)
C12—N3—C11—C3	−164.74 (13)	N1B—C2B—C3B—C4B	−176.69 (12)
C4—C3—C11—N2	36.9 (2)	C2B—C3B—C4B—C5B	−2.2 (2)
C2—C3—C11—N2	−147.44 (15)	C2B—C3B—C4B—N2B	176.57 (12)
C4—C3—C11—N3	−142.10 (15)	O4B—N2B—C4B—C5B	177.81 (13)
C2—C3—C11—N3	33.6 (2)	O5B—N2B—C4B—C5B	−1.8 (2)
C11—N3—C12—C13	−121.45 (15)	O4B—N2B—C4B—C3B	−0.97 (19)
C15—N3—C12—C13	55.18 (15)	O5B—N2B—C4B—C3B	179.42 (13)
C16—N4—C13—C12	178.99 (13)	C3B—C4B—C5B—C6B	2.1 (2)
C14—N4—C13—C12	55.07 (16)	N2B—C4B—C5B—C6B	−176.65 (13)
N3—C12—C13—N4	−54.21 (16)	C4B—C5B—C6B—C1B	−1.2 (2)
C16—N4—C14—C15	177.80 (13)	C4B—C5B—C6B—N3B	178.58 (13)
C13—N4—C14—C15	−57.33 (15)	O1B—C1B—C6B—C5B	−177.01 (14)
C11—N3—C15—C14	119.67 (14)	C2B—C1B—C6B—C5B	0.4 (2)
C12—N3—C15—C14	−57.02 (15)	O1B—C1B—C6B—N3B	3.2 (2)
N4—C14—C15—N3	58.41 (15)	C2B—C1B—C6B—N3B	−179.37 (12)
O1A—C1A—C2A—C3A	165.04 (15)	O6B—N3B—C6B—C5B	19.5 (2)
C6A—C1A—C2A—C3A	−10.9 (2)	O7B—N3B—C6B—C5B	−159.31 (15)
O1A—C1A—C2A—N1A	−12.8 (2)	O6B—N3B—C6B—C1B	−160.69 (15)
C6A—C1A—C2A—N1A	171.21 (13)	O7B—N3B—C6B—C1B	20.5 (2)
O2AB—N1A—C2A—C3A	−153.8 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1A	0.872 (17)	1.848 (17)	2.7086 (17)	168.5 (16)
N4—H4···O1B	0.926 (19)	1.859 (19)	2.6612 (17)	143.6 (17)
N4—H4···O7B	0.926 (19)	2.449 (19)	3.1714 (19)	135.0 (15)
N1—H1···O5Bi	0.852 (19)	2.40 (2)	3.1395 (18)	145.9 (17)
C5B—H5B···S1ii	0.93	2.87	3.6225 (15)	139
C8—H8···O3Aiii	0.93	2.48	3.349 (2)	156
C12—H12A···O5Aiv	0.97	2.23	3.0970 (19)	149
C17—H17B···O6Aiv	0.96	2.43	3.207 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1A	0.872 (17)	1.848 (17)	2.7086 (17)	168.5 (16)
N4—H4⋯O1B	0.926 (19)	1.859 (19)	2.6612 (17)	143.6 (17)
N4—H4⋯O7B	0.926 (19)	2.449 (19)	3.1714 (19)	135.0 (15)
N1—H1⋯O5B i	0.852 (19)	2.40 (2)	3.1395 (18)	145.9 (17)
C5B—H5B⋯S1ii	0.93	2.87	3.6225 (15)	139
C8—H8⋯O3A iii	0.93	2.48	3.349 (2)	156
C12—H12A⋯O5A iv	0.97	2.23	3.0970 (19)	149
C17—H17B⋯O6A iv	0.96	2.43	3.207 (2)	138

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