2-Methyl-4-(4-methyl-piperazin-1-yl)-10H-thieno[2,3-b][1,5]benzodiazepine (olanzapine) propan-2-ol disolvate.

In the title solvate, C17H20N4S·2C3H8O, pairs of olanzapine mol-ecules related by a centre of inversion stack along the a axis, forming columns, which are packed parallel to each other along the b axis, forming a sheet arrangement. The columns within these sheets are hydrogen bonded to each other through the propan-2-ol solvent mol-ecules. The diazepine ring of the olanzapine exists in a puckered conformation with the thiophene and phenyl rings making a dihedral angle of 57.66 (7)° and the piperazine ring adopts a chair conformation with the methyl group in an equatorial position.

Related literature

For literature on olanzapine and related structural studies, see: Fulton & Goa (1997 ▶); Sanger et al. (2001 ▶); Tollefson et al. (1997 ▶); Reutzel-Edens et al. (2003 ▶); Bhardwaj et al. (2013 ▶). For details of experimental methods used, see: Florence et al. (2003 ▶). For details of XPac, see: Gelbrich & Hursthouse (2005 ▶).

Experimental

Crystal data

C17H20N4S·2C3H8O

M = 432.62

Triclinic,

a = 9.9621 (5) Å

b = 10.8702 (6) Å

c = 12.2298 (7) Å

α = 70.421 (2)°

β = 74.560 (2)°

γ = 77.296 (2)°

V = 1190.24 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.16 mm−1

T = 123 K

0.41 × 0.34 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.581, T max = 0.745

16365 measured reflections

4880 independent reflections

4073 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.106

S = 1.04

4880 reflections

289 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶) and WinGX (Farrugia, 2012 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and WinGX (Farrugia, 2012 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶) and ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813009811/fj2624sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009811/fj2624Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009811/fj2624Isup3.cml

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

C17H20N4S·2C3H8O	Z = 2
Mr = 432.62	F(000) = 468
Triclinic, P1	Dx = 1.207 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9621 (5) Å	Cell parameters from 8504 reflections
b = 10.8702 (6) Å	θ = 2.3–26.5°
c = 12.2298 (7) Å	µ = 0.16 mm−1
α = 70.421 (2)°	T = 123 K
β = 74.560 (2)°	Plate, yellow
γ = 77.296 (2)°	0.41 × 0.34 × 0.11 mm
V = 1190.24 (11) Å3

Bruker APEXII CCD diffractometer	4880 independent reflections
Radiation source: fine-focus sealed tube	4073 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 26.6°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→10
Tmin = 0.581, Tmax = 0.745	k = −11→13
16365 measured reflections	l = −15→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.055P)2 + 0.4568P] where P = (Fo2 + 2Fc2)/3
4880 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
H1N	−0.1193 (19)	0.9466 (19)	0.1993 (16)	0.032 (5)*
H3S	0.514 (2)	0.758 (2)	0.825 (2)	0.050 (6)*
H1S	0.260 (3)	0.830 (2)	0.854 (2)	0.058 (7)*
S1	0.04115 (4)	0.91878 (4)	0.36298 (3)	0.02407 (11)
N1	−0.09642 (13)	0.85854 (13)	0.22328 (11)	0.0230 (3)
N4	0.36303 (13)	0.26018 (12)	0.32261 (11)	0.0219 (3)
N3	0.14149 (12)	0.47811 (12)	0.30511 (11)	0.0217 (3)
N2	−0.08278 (13)	0.56928 (12)	0.28169 (11)	0.0219 (3)
C14	0.21368 (16)	0.24248 (14)	0.35573 (14)	0.0244 (3)
H14A	0.1787	0.2325	0.4415	0.029*
H14B	0.2046	0.1606	0.3414	0.029*
C16	0.28887 (15)	0.49962 (14)	0.26562 (14)	0.0223 (3)
H16A	0.2985	0.5831	0.2769	0.027*
H16B	0.3210	0.5068	0.1801	0.027*
C5	0.03110 (15)	0.57973 (14)	0.30703 (12)	0.0200 (3)
C6	0.13109 (15)	0.67258 (14)	0.43396 (13)	0.0213 (3)
H6	0.1755	0.5898	0.4756	0.026*
C7	0.13712 (15)	0.78773 (15)	0.45145 (13)	0.0228 (3)
C13	0.12395 (16)	0.35797 (14)	0.28589 (14)	0.0229 (3)
H13A	0.1534	0.3649	0.2003	0.027*
H13B	0.0238	0.3448	0.3126	0.027*
C12	−0.33300 (16)	0.60148 (15)	0.33644 (13)	0.0246 (3)
H12	−0.3275	0.5082	0.3590	0.030*
C3	−0.21953 (15)	0.79562 (14)	0.26365 (12)	0.0211 (3)
C15	0.37834 (16)	0.38554 (15)	0.33649 (14)	0.0243 (3)
H15A	0.4783	0.3993	0.3090	0.029*
H15B	0.3493	0.3817	0.4214	0.029*
C2	−0.00519 (15)	0.81452 (14)	0.30203 (13)	0.0208 (3)
C10	−0.47383 (16)	0.81431 (16)	0.30737 (14)	0.0259 (3)
H10	−0.5633	0.8678	0.3091	0.031*
C4	−0.20831 (15)	0.65708 (14)	0.29640 (13)	0.0213 (3)
C8	0.20862 (17)	0.81074 (16)	0.53509 (15)	0.0273 (3)
H8A	0.1404	0.8144	0.6087	0.041*
H8B	0.2467	0.8944	0.4981	0.041*
H8C	0.2854	0.7384	0.5530	0.041*
C17	0.44267 (18)	0.14983 (16)	0.39751 (15)	0.0301 (4)
H17A	0.5423	0.1610	0.3746	0.045*
H17B	0.4325	0.0669	0.3873	0.045*
H17C	0.4066	0.1476	0.4808	0.045*
C11	−0.46419 (16)	0.67801 (16)	0.34425 (14)	0.0259 (3)
H11	−0.5471	0.6373	0.3747	0.031*
C1	0.05185 (15)	0.68643 (14)	0.34722 (13)	0.0206 (3)
C9	−0.35177 (16)	0.87206 (15)	0.26790 (13)	0.0241 (3)
H9	−0.3585	0.9655	0.2433	0.029*
O1S	0.44594 (13)	0.77562 (13)	0.87986 (11)	0.0348 (3)
C2S	0.50035 (18)	0.80746 (17)	0.96257 (14)	0.0318 (4)
H2S	0.5619	0.8773	0.9179	0.038*
C3S	0.58641 (19)	0.6878 (2)	1.02927 (16)	0.0425 (5)
H3S1	0.5278	0.6176	1.0712	0.064*
H3S2	0.6211	0.7107	1.0868	0.064*
H3S3	0.6664	0.6572	0.9733	0.064*
C1S	0.3754 (2)	0.8628 (2)	1.04315 (16)	0.0420 (5)
H1S1	0.3228	0.9397	0.9952	0.063*
H1S2	0.4087	0.8892	1.0994	0.063*
H1S3	0.3140	0.7952	1.0869	0.063*
O2S	0.17158 (13)	0.85357 (11)	0.84879 (10)	0.0308 (3)
C5S	0.08774 (19)	0.77005 (18)	0.94873 (15)	0.0345 (4)
H6S	0.1012	0.7803	1.0232	0.041*
C4S	−0.0636 (2)	0.8177 (2)	0.93962 (18)	0.0464 (5)
H5S1	−0.0883	0.9095	0.9413	0.070*
H5S2	−0.1242	0.7625	1.0066	0.070*
H5S3	−0.0771	0.8120	0.8650	0.070*
C6S	0.1325 (3)	0.62811 (19)	0.9508 (2)	0.0577 (6)
H7S1	0.1192	0.6169	0.8783	0.087*
H7S2	0.0755	0.5723	1.0202	0.087*
H7S3	0.2320	0.6026	0.9552	0.087*

	U11	U22	U33	U12	U13	U23
S1	0.0235 (2)	0.01788 (19)	0.0328 (2)	−0.00162 (14)	−0.00854 (15)	−0.00866 (15)
N1	0.0219 (6)	0.0188 (6)	0.0268 (6)	−0.0008 (5)	−0.0093 (5)	−0.0029 (5)
N4	0.0211 (6)	0.0199 (6)	0.0267 (6)	0.0027 (5)	−0.0098 (5)	−0.0092 (5)
N3	0.0173 (6)	0.0179 (6)	0.0316 (7)	−0.0013 (5)	−0.0065 (5)	−0.0092 (5)
N2	0.0208 (6)	0.0206 (6)	0.0259 (6)	−0.0006 (5)	−0.0085 (5)	−0.0074 (5)
C14	0.0241 (8)	0.0187 (7)	0.0306 (8)	−0.0019 (6)	−0.0050 (6)	−0.0088 (6)
C16	0.0181 (7)	0.0198 (7)	0.0306 (8)	−0.0027 (6)	−0.0051 (6)	−0.0096 (6)
C5	0.0203 (7)	0.0181 (7)	0.0208 (7)	−0.0029 (6)	−0.0051 (6)	−0.0039 (5)
C6	0.0182 (7)	0.0204 (7)	0.0258 (7)	−0.0008 (6)	−0.0063 (6)	−0.0072 (6)
C7	0.0188 (7)	0.0232 (7)	0.0272 (7)	−0.0017 (6)	−0.0054 (6)	−0.0088 (6)
C13	0.0202 (7)	0.0201 (7)	0.0310 (8)	−0.0023 (6)	−0.0068 (6)	−0.0103 (6)
C12	0.0247 (8)	0.0246 (8)	0.0283 (8)	−0.0023 (6)	−0.0121 (6)	−0.0082 (6)
C3	0.0210 (7)	0.0236 (7)	0.0201 (7)	−0.0008 (6)	−0.0074 (6)	−0.0071 (6)
C15	0.0210 (7)	0.0249 (8)	0.0315 (8)	0.0009 (6)	−0.0098 (6)	−0.0135 (6)
C2	0.0171 (7)	0.0209 (7)	0.0253 (7)	−0.0022 (6)	−0.0044 (6)	−0.0084 (6)
C10	0.0201 (7)	0.0337 (9)	0.0267 (8)	0.0042 (6)	−0.0096 (6)	−0.0140 (7)
C4	0.0211 (7)	0.0231 (7)	0.0223 (7)	0.0005 (6)	−0.0099 (6)	−0.0082 (6)
C8	0.0261 (8)	0.0267 (8)	0.0346 (8)	−0.0025 (6)	−0.0105 (7)	−0.0138 (7)
C17	0.0330 (9)	0.0266 (8)	0.0309 (8)	0.0065 (7)	−0.0143 (7)	−0.0094 (7)
C11	0.0201 (7)	0.0337 (8)	0.0279 (8)	−0.0037 (6)	−0.0083 (6)	−0.0119 (6)
C1	0.0167 (7)	0.0201 (7)	0.0256 (7)	−0.0008 (6)	−0.0050 (6)	−0.0084 (6)
C9	0.0259 (8)	0.0225 (7)	0.0244 (7)	0.0027 (6)	−0.0100 (6)	−0.0079 (6)
O1S	0.0261 (6)	0.0516 (8)	0.0322 (6)	0.0042 (5)	−0.0095 (5)	−0.0228 (6)
C2S	0.0355 (9)	0.0347 (9)	0.0283 (8)	−0.0080 (7)	−0.0084 (7)	−0.0104 (7)
C3S	0.0288 (9)	0.0608 (13)	0.0309 (9)	0.0016 (9)	−0.0060 (7)	−0.0098 (9)
C1S	0.0504 (12)	0.0442 (11)	0.0350 (10)	0.0068 (9)	−0.0151 (9)	−0.0201 (8)
O2S	0.0258 (6)	0.0242 (6)	0.0362 (6)	−0.0032 (5)	−0.0058 (5)	−0.0019 (5)
C5S	0.0340 (9)	0.0412 (10)	0.0281 (8)	−0.0136 (8)	−0.0074 (7)	−0.0042 (7)
C4S	0.0314 (10)	0.0684 (14)	0.0401 (10)	−0.0170 (9)	−0.0035 (8)	−0.0139 (10)
C6S	0.0651 (15)	0.0318 (10)	0.0726 (15)	−0.0172 (10)	−0.0297 (12)	0.0074 (10)

S1—C7	1.7415 (15)	C10—C11	1.386 (2)
S1—C2	1.7415 (15)	C10—C9	1.388 (2)
N1—C2	1.3959 (19)	C10—H10	0.9500
N1—C3	1.4268 (19)	C8—H8A	0.9800
N1—H1N	0.897 (19)	C8—H8B	0.9800
N4—C17	1.4627 (19)	C8—H8C	0.9800
N4—C14	1.4723 (19)	C17—H17A	0.9800
N4—C15	1.4728 (18)	C17—H17B	0.9800
N3—C5	1.3782 (18)	C17—H17C	0.9800
N3—C13	1.4558 (18)	C11—H11	0.9500
N3—C16	1.4633 (18)	C9—H9	0.9500
N2—C5	1.2897 (19)	O1S—C2S	1.430 (2)
N2—C4	1.4061 (18)	O1S—H3S	0.86 (2)
C14—C13	1.516 (2)	C2S—C3S	1.504 (2)
C14—H14A	0.9900	C2S—C1S	1.515 (2)
C14—H14B	0.9900	C2S—H2S	1.0000
C16—C15	1.513 (2)	C3S—H3S1	0.9800
C16—H16A	0.9900	C3S—H3S2	0.9800
C16—H16B	0.9900	C3S—H3S3	0.9800
C5—C1	1.474 (2)	C1S—H1S1	0.9800
C6—C7	1.355 (2)	C1S—H1S2	0.9800
C6—C1	1.434 (2)	C1S—H1S3	0.9800
C6—H6	0.9500	O2S—C5S	1.436 (2)
C7—C8	1.501 (2)	O2S—H1S	0.87 (2)
C13—H13A	0.9900	C5S—C6S	1.502 (3)
C13—H13B	0.9900	C5S—C4S	1.504 (3)
C12—C11	1.385 (2)	C5S—H6S	1.0000
C12—C4	1.399 (2)	C4S—H5S1	0.9800
C12—H12	0.9500	C4S—H5S2	0.9800
C3—C9	1.393 (2)	C4S—H5S3	0.9800
C3—C4	1.409 (2)	C6S—H7S1	0.9800
C15—H15A	0.9900	C6S—H7S2	0.9800
C15—H15B	0.9900	C6S—H7S3	0.9800
C2—C1	1.368 (2)
C7—S1—C2	91.98 (7)	C7—C8—H8A	109.5
C2—N1—C3	114.13 (12)	C7—C8—H8B	109.5
C2—N1—H1N	113.8 (12)	H8A—C8—H8B	109.5
C3—N1—H1N	110.7 (12)	C7—C8—H8C	109.5
C17—N4—C14	109.50 (12)	H8A—C8—H8C	109.5
C17—N4—C15	110.02 (12)	H8B—C8—H8C	109.5
C14—N4—C15	110.22 (11)	N4—C17—H17A	109.5
C5—N3—C13	120.29 (12)	N4—C17—H17B	109.5
C5—N3—C16	122.85 (12)	H17A—C17—H17B	109.5
C13—N3—C16	110.77 (11)	N4—C17—H17C	109.5
C5—N2—C4	123.11 (13)	H17A—C17—H17C	109.5
N4—C14—C13	112.02 (12)	H17B—C17—H17C	109.5
N4—C14—H14A	109.2	C12—C11—C10	119.60 (14)
C13—C14—H14A	109.2	C12—C11—H11	120.2
N4—C14—H14B	109.2	C10—C11—H11	120.2
C13—C14—H14B	109.2	C2—C1—C6	112.09 (13)
H14A—C14—H14B	107.9	C2—C1—C5	121.52 (13)
N3—C16—C15	109.49 (12)	C6—C1—C5	126.38 (13)
N3—C16—H16A	109.8	C10—C9—C3	121.24 (14)
C15—C16—H16A	109.8	C10—C9—H9	119.4
N3—C16—H16B	109.8	C3—C9—H9	119.4
C15—C16—H16B	109.8	C2S—O1S—H3S	109.0 (15)
H16A—C16—H16B	108.2	O1S—C2S—C3S	110.46 (14)
N2—C5—N3	118.01 (13)	O1S—C2S—C1S	106.97 (14)
N2—C5—C1	126.03 (13)	C3S—C2S—C1S	112.88 (15)
N3—C5—C1	115.78 (12)	O1S—C2S—H2S	108.8
C7—C6—C1	114.22 (13)	C3S—C2S—H2S	108.8
C7—C6—H6	122.9	C1S—C2S—H2S	108.8
C1—C6—H6	122.9	C2S—C3S—H3S1	109.5
C6—C7—C8	128.92 (14)	C2S—C3S—H3S2	109.5
C6—C7—S1	110.50 (11)	H3S1—C3S—H3S2	109.5
C8—C7—S1	120.55 (11)	C2S—C3S—H3S3	109.5
N3—C13—C14	108.59 (12)	H3S1—C3S—H3S3	109.5
N3—C13—H13A	110.0	H3S2—C3S—H3S3	109.5
C14—C13—H13A	110.0	C2S—C1S—H1S1	109.5
N3—C13—H13B	110.0	C2S—C1S—H1S2	109.5
C14—C13—H13B	110.0	H1S1—C1S—H1S2	109.5
H13A—C13—H13B	108.4	C2S—C1S—H1S3	109.5
C11—C12—C4	122.09 (14)	H1S1—C1S—H1S3	109.5
C11—C12—H12	119.0	H1S2—C1S—H1S3	109.5
C4—C12—H12	119.0	C5S—O2S—H1S	108.9 (15)
C9—C3—C4	119.78 (14)	O2S—C5S—C6S	110.43 (16)
C9—C3—N1	119.63 (13)	O2S—C5S—C4S	107.23 (14)
C4—C3—N1	120.57 (13)	C6S—C5S—C4S	112.72 (17)
N4—C15—C16	110.50 (12)	O2S—C5S—H6S	108.8
N4—C15—H15A	109.5	C6S—C5S—H6S	108.8
C16—C15—H15A	109.5	C4S—C5S—H6S	108.8
N4—C15—H15B	109.5	C5S—C4S—H5S1	109.5
C16—C15—H15B	109.5	C5S—C4S—H5S2	109.5
H15A—C15—H15B	108.1	H5S1—C4S—H5S2	109.5
C1—C2—N1	125.87 (13)	C5S—C4S—H5S3	109.5
C1—C2—S1	111.18 (11)	H5S1—C4S—H5S3	109.5
N1—C2—S1	122.83 (11)	H5S2—C4S—H5S3	109.5
C11—C10—C9	119.46 (14)	C5S—C6S—H7S1	109.5
C11—C10—H10	120.3	C5S—C6S—H7S2	109.5
C9—C10—H10	120.3	H7S1—C6S—H7S2	109.5
C12—C4—N2	116.18 (13)	C5S—C6S—H7S3	109.5
C12—C4—C3	117.75 (13)	H7S1—C6S—H7S3	109.5
N2—C4—C3	125.76 (13)	H7S2—C6S—H7S3	109.5
C17—N4—C14—C13	176.70 (12)	C7—S1—C2—N1	175.64 (13)
C15—N4—C14—C13	55.54 (16)	C11—C12—C4—N2	−173.92 (13)
C5—N3—C16—C15	146.27 (13)	C11—C12—C4—C3	0.1 (2)
C13—N3—C16—C15	−61.22 (15)	C5—N2—C4—C12	−142.24 (15)
C4—N2—C5—N3	171.00 (13)	C5—N2—C4—C3	44.3 (2)
C4—N2—C5—C1	−4.0 (2)	C9—C3—C4—C12	−2.3 (2)
C13—N3—C5—N2	−5.6 (2)	N1—C3—C4—C12	179.32 (13)
C16—N3—C5—N2	144.38 (14)	C9—C3—C4—N2	171.08 (13)
C13—N3—C5—C1	169.89 (13)	N1—C3—C4—N2	−7.3 (2)
C16—N3—C5—C1	−40.10 (19)	C4—C12—C11—C10	2.5 (2)
C1—C6—C7—C8	179.38 (15)	C9—C10—C11—C12	−2.8 (2)
C1—C6—C7—S1	1.28 (16)	N1—C2—C1—C6	−174.71 (13)
C2—S1—C7—C6	−0.43 (12)	S1—C2—C1—C6	1.34 (16)
C2—S1—C7—C8	−178.71 (13)	N1—C2—C1—C5	5.7 (2)
C5—N3—C13—C14	−146.81 (13)	S1—C2—C1—C5	−178.28 (11)
C16—N3—C13—C14	59.88 (15)	C7—C6—C1—C2	−1.73 (19)
N4—C14—C13—N3	−57.24 (16)	C7—C6—C1—C5	177.87 (13)
C2—N1—C3—C9	126.29 (14)	N2—C5—C1—C2	−38.1 (2)
C2—N1—C3—C4	−55.31 (18)	N3—C5—C1—C2	146.84 (14)
C17—N4—C15—C16	−176.32 (13)	N2—C5—C1—C6	142.37 (16)
C14—N4—C15—C16	−55.47 (16)	N3—C5—C1—C6	−32.7 (2)
N3—C16—C15—N4	58.31 (16)	C11—C10—C9—C3	0.6 (2)
C3—N1—C2—C1	55.2 (2)	C4—C3—C9—C10	2.0 (2)
C3—N1—C2—S1	−120.37 (13)	N1—C3—C9—C10	−179.59 (13)
C7—S1—C2—C1	−0.55 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2Si	0.90 (2)	2.04 (2)	2.933 (2)	177 (2)
O1S—H3S···N4ii	0.86 (2)	1.94 (2)	2.778 (2)	167 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2S i	0.90 (2)	2.04 (2)	2.933 (2)	177 (2)
O1S—H3S⋯N4ii	0.86 (2)	1.94 (2)	2.778 (2)	167 (2)

Symmetry codes: (i) ; (ii) .