3-Hydr-oxy-4-methoxy-benzaldehyde thio-semicarbazone hemihydrate.

The asymmetric unit of the title compound, C(9)H(11)N(3)O(2)S·0.5H(2)O, comprises two crystallograpically independent thio-semicarbazone mol-ecules (A and B) and a water mol-ecule of crystallization. In each of the thio-semicarbazone mol-ecules, intra-molecular O-H⋯O and N-H⋯N hydrogen bonds form five-membered rings, producing S(5) ring motifs. Inter-molecular O-H⋯S and N-H⋯O inter-actions between mol-ecule B and the water mol-ecule form a six-membered ring, producing an R(2) (2)(6) ring motif. Inter-molecular N-H⋯S hydrogen bonds form dimers involving pairs of both A and B mol-ecules, which form R(2) (2)(8) ring motifs. The angles between the aromatic ring and thio-urea unit in the two mol-ecules are 0.80 (6) and 3.28 (5)°, which proves that each mol-ecule is fairly planar. The crystal structure is stabilized by inter-molecular O-H⋯S (×2), O-H⋯O, N-H⋯S (×2) and N-H⋯O (×2) hydrogen bonds and C-H⋯O (×2) contacts to form a three-dimensional network.

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For background to thio­semicarbazones, see: Al-Awadi et al. (2008 ▶); Kizilcikli et al. (2004 ▶); Mishra et al. (2006 ▶). For a related structure, see: Ferrari et al. (2001 ▶).

Experimental

Crystal data

C9H11N3O2S·0.5H2O

M = 234.28

Triclinic,

a = 10.5288 (2) Å

b = 10.7045 (2) Å

c = 11.8154 (2) Å

α = 68.438 (1)°

β = 68.917 (1)°

γ = 68.114 (1)°

V = 1110.28 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 100.0 (1) K

0.45 × 0.32 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.884, T max = 0.973

45467 measured reflections

10830 independent reflections

8078 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.116

S = 1.10

10830 reflections

314 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.90 e Å−3

Δρmin = −0.63 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035617/tk2321sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035617/tk2321Isup2.hkl

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

C9H11N3O2S·0.5H2O	Z = 4
Mr = 234.28	F000 = 492
Triclinic, P1	Dx = 1.402 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 10.5288 (2) Å	Cell parameters from 9992 reflections
b = 10.7045 (2) Å	θ = 2.5–36.3º
c = 11.8154 (2) Å	µ = 0.28 mm−1
α = 68.438 (1)º	T = 100.0 (1) K
β = 68.917 (1)º	Plate, light yellow
γ = 68.114 (1)º	0.45 × 0.32 × 0.10 mm
V = 1110.28 (4) Å3

Bruker SMART APEXII CCD area-detector diffractometer	10830 independent reflections
Radiation source: fine-focus sealed tube	8078 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.040
T = 100.0(1) K	θmax = 36.6º
φ and ω scans	θmin = 2.1º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −17→17
Tmin = 0.884, Tmax = 0.973	k = −17→17
45467 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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.0547P)2 + 0.1125P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.001
10830 reflections	Δρmax = 0.90 e Å−3
314 parameters	Δρmin = −0.63 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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.

	x	y	z	Uiso*/Ueq
S1A	0.96703 (3)	0.48913 (3)	0.19973 (2)	0.01747 (6)
O1A	0.51514 (8)	0.27402 (9)	−0.26347 (7)	0.02001 (15)
O2A	0.30169 (8)	0.21411 (9)	−0.07261 (7)	0.01997 (15)
N1A	0.71556 (9)	0.38149 (9)	0.09845 (8)	0.01559 (15)
N2A	0.82582 (9)	0.42443 (9)	0.09440 (8)	0.01634 (15)
N3A	0.72833 (10)	0.41202 (10)	0.30323 (9)	0.01863 (16)
C1A	0.60929 (10)	0.32375 (11)	−0.13430 (9)	0.01602 (17)
H1AA	0.6832	0.3453	−0.2035	0.019*
C2A	0.50692 (10)	0.28289 (11)	−0.14735 (9)	0.01535 (16)
C3A	0.39489 (10)	0.25053 (10)	−0.04411 (9)	0.01556 (16)
C4A	0.38655 (10)	0.25938 (11)	0.07304 (9)	0.01677 (17)
H4AA	0.3126	0.2376	0.1421	0.020*
C5A	0.48947 (10)	0.30101 (11)	0.08621 (9)	0.01594 (17)
H5AA	0.4835	0.3078	0.1643	0.019*
C6A	0.60192 (10)	0.33279 (10)	−0.01652 (9)	0.01479 (16)
C7A	0.71238 (10)	0.37674 (11)	−0.00763 (9)	0.01642 (17)
H7AA	0.7819	0.4018	−0.0799	0.020*
C8A	0.83058 (10)	0.43992 (10)	0.20092 (9)	0.01451 (16)
C9A	0.18681 (12)	0.17340 (13)	0.02852 (11)	0.0237 (2)
H9AA	0.1261	0.1552	−0.0041	0.036*
H9AB	0.1337	0.2473	0.0688	0.036*
H9AC	0.2236	0.0904	0.0886	0.036*
S1B	0.47040 (3)	0.21971 (3)	0.47447 (3)	0.02029 (6)
O1B	0.02689 (9)	−0.32448 (8)	0.32698 (8)	0.02095 (15)
O2B	−0.18810 (8)	−0.11332 (8)	0.24783 (7)	0.01905 (14)
N1B	0.20913 (9)	0.10835 (9)	0.38890 (8)	0.01597 (15)
N2B	0.31944 (9)	0.10741 (9)	0.42677 (8)	0.01711 (15)
N3B	0.23043 (10)	0.34380 (10)	0.39796 (9)	0.02002 (17)
C1B	0.10696 (10)	−0.16764 (10)	0.36407 (9)	0.01606 (17)
H1BA	0.1780	−0.2427	0.3942	0.019*
C2B	0.01113 (10)	−0.19098 (10)	0.32466 (9)	0.01548 (16)
C3B	−0.09831 (10)	−0.07809 (10)	0.28235 (9)	0.01488 (16)
C4B	−0.10910 (10)	0.05636 (10)	0.27978 (9)	0.01613 (17)
H4BA	−0.1822	0.1310	0.2526	0.019*
C5B	−0.01134 (10)	0.07990 (10)	0.31756 (9)	0.01574 (16)
H5BA	−0.0188	0.1701	0.3152	0.019*
C6B	0.09823 (10)	−0.03191 (10)	0.35910 (9)	0.01469 (16)
C7B	0.20549 (10)	−0.01329 (10)	0.39715 (9)	0.01585 (17)
H7BA	0.2733	−0.0917	0.4283	0.019*
C8B	0.32919 (10)	0.22659 (11)	0.43096 (9)	0.01633 (17)
C9B	−0.30345 (11)	−0.00063 (12)	0.20815 (11)	0.0222 (2)
H9BA	−0.3624	−0.0365	0.1894	0.033*
H9BB	−0.2670	0.0658	0.1342	0.033*
H9BC	−0.3583	0.0444	0.2743	0.033*
O1W	0.34588 (8)	0.53871 (8)	0.45766 (7)	0.02077 (15)
H2W1	0.3911	0.4524	0.4611	0.031*
H1W1	0.3945	0.5902	0.3981	0.031*
H2NA	0.8880 (18)	0.4499 (18)	0.0167 (16)	0.037 (4)*
H2NB	0.3777 (17)	0.0311 (18)	0.4514 (15)	0.032 (4)*
H3NA	0.6636 (16)	0.3855 (16)	0.3001 (14)	0.025 (4)*
H3NB	0.7234 (15)	0.4214 (16)	0.3744 (14)	0.025 (4)*
H3NC	0.2333 (17)	0.4172 (18)	0.4051 (15)	0.033 (4)*
H3ND	0.1594 (16)	0.3384 (16)	0.3798 (14)	0.026 (4)*
H1OA	0.4418 (18)	0.2630 (18)	−0.2614 (16)	0.036 (4)*
H1OB	−0.0391 (18)	−0.3255 (18)	0.3063 (16)	0.037 (4)*

	U11	U22	U33	U12	U13	U23
S1A	0.01803 (11)	0.02175 (12)	0.01820 (11)	−0.01016 (9)	−0.00575 (8)	−0.00572 (9)
O1A	0.0214 (3)	0.0294 (4)	0.0160 (3)	−0.0126 (3)	−0.0040 (3)	−0.0087 (3)
O2A	0.0179 (3)	0.0289 (4)	0.0197 (3)	−0.0134 (3)	−0.0029 (3)	−0.0087 (3)
N1A	0.0144 (3)	0.0177 (4)	0.0181 (4)	−0.0063 (3)	−0.0058 (3)	−0.0050 (3)
N2A	0.0165 (3)	0.0214 (4)	0.0155 (3)	−0.0096 (3)	−0.0047 (3)	−0.0048 (3)
N3A	0.0176 (4)	0.0251 (4)	0.0174 (4)	−0.0100 (3)	−0.0029 (3)	−0.0079 (3)
C1A	0.0152 (4)	0.0199 (4)	0.0155 (4)	−0.0075 (3)	−0.0031 (3)	−0.0057 (3)
C2A	0.0166 (4)	0.0179 (4)	0.0149 (4)	−0.0063 (3)	−0.0049 (3)	−0.0057 (3)
C3A	0.0144 (4)	0.0174 (4)	0.0179 (4)	−0.0066 (3)	−0.0047 (3)	−0.0054 (3)
C4A	0.0162 (4)	0.0203 (4)	0.0156 (4)	−0.0079 (3)	−0.0031 (3)	−0.0048 (3)
C5A	0.0163 (4)	0.0197 (4)	0.0141 (4)	−0.0068 (3)	−0.0042 (3)	−0.0049 (3)
C6A	0.0142 (4)	0.0165 (4)	0.0160 (4)	−0.0052 (3)	−0.0051 (3)	−0.0047 (3)
C7A	0.0151 (4)	0.0193 (4)	0.0172 (4)	−0.0070 (3)	−0.0045 (3)	−0.0048 (3)
C8A	0.0147 (4)	0.0142 (4)	0.0167 (4)	−0.0042 (3)	−0.0058 (3)	−0.0045 (3)
C9A	0.0193 (4)	0.0321 (6)	0.0253 (5)	−0.0151 (4)	−0.0009 (4)	−0.0105 (4)
S1B	0.01952 (11)	0.01809 (12)	0.02886 (13)	−0.00806 (9)	−0.01069 (10)	−0.00520 (9)
O1B	0.0208 (3)	0.0155 (3)	0.0330 (4)	−0.0036 (3)	−0.0123 (3)	−0.0099 (3)
O2B	0.0178 (3)	0.0175 (3)	0.0280 (4)	−0.0032 (3)	−0.0118 (3)	−0.0089 (3)
N1B	0.0142 (3)	0.0186 (4)	0.0181 (4)	−0.0064 (3)	−0.0052 (3)	−0.0054 (3)
N2B	0.0157 (3)	0.0157 (4)	0.0236 (4)	−0.0053 (3)	−0.0086 (3)	−0.0049 (3)
N3B	0.0193 (4)	0.0159 (4)	0.0279 (4)	−0.0046 (3)	−0.0095 (3)	−0.0061 (3)
C1B	0.0148 (4)	0.0152 (4)	0.0201 (4)	−0.0028 (3)	−0.0063 (3)	−0.0065 (3)
C2B	0.0158 (4)	0.0141 (4)	0.0191 (4)	−0.0044 (3)	−0.0049 (3)	−0.0067 (3)
C3B	0.0146 (4)	0.0169 (4)	0.0164 (4)	−0.0057 (3)	−0.0047 (3)	−0.0059 (3)
C4B	0.0168 (4)	0.0152 (4)	0.0187 (4)	−0.0045 (3)	−0.0072 (3)	−0.0045 (3)
C5B	0.0170 (4)	0.0137 (4)	0.0183 (4)	−0.0050 (3)	−0.0058 (3)	−0.0044 (3)
C6B	0.0148 (4)	0.0156 (4)	0.0158 (4)	−0.0055 (3)	−0.0041 (3)	−0.0050 (3)
C7B	0.0150 (4)	0.0164 (4)	0.0182 (4)	−0.0050 (3)	−0.0054 (3)	−0.0051 (3)
C8B	0.0165 (4)	0.0172 (4)	0.0173 (4)	−0.0073 (3)	−0.0039 (3)	−0.0045 (3)
C9B	0.0193 (4)	0.0214 (5)	0.0322 (5)	−0.0022 (4)	−0.0141 (4)	−0.0104 (4)
O1W	0.0225 (4)	0.0180 (3)	0.0206 (3)	−0.0044 (3)	−0.0056 (3)	−0.0051 (3)

S1A—C8A	1.6988 (10)	O1B—C2B	1.3668 (12)
O1A—C2A	1.3794 (11)	O1B—H1OB	0.820 (17)
O1A—H1OA	0.814 (17)	O2B—C3B	1.3633 (12)
O2A—C3A	1.3593 (12)	O2B—C9B	1.4324 (12)
O2A—C9A	1.4322 (13)	N1B—C7B	1.2836 (13)
N1A—C7A	1.2857 (12)	N1B—N2B	1.3824 (11)
N1A—N2A	1.3794 (12)	N2B—C8B	1.3373 (13)
N2A—C8A	1.3486 (12)	N2B—H2NB	0.841 (17)
N2A—H2NA	0.928 (17)	N3B—C8B	1.3292 (13)
N3A—C8A	1.3219 (13)	N3B—H3NC	0.832 (17)
N3A—H3NA	0.847 (16)	N3B—H3ND	0.875 (16)
N3A—H3NB	0.864 (15)	C1B—C2B	1.3816 (13)
C1A—C2A	1.3776 (13)	C1B—C6B	1.4016 (14)
C1A—C6A	1.4028 (13)	C1B—H1BA	0.9300
C1A—H1AA	0.9300	C2B—C3B	1.4037 (13)
C2A—C3A	1.3993 (14)	C3B—C4B	1.3905 (14)
C3A—C4A	1.3912 (13)	C4B—C5B	1.3888 (13)
C4A—C5A	1.3890 (14)	C4B—H4BA	0.9300
C4A—H4AA	0.9300	C5B—C6B	1.3966 (13)
C5A—C6A	1.3977 (14)	C5B—H5BA	0.9300
C5A—H5AA	0.9300	C6B—C7B	1.4547 (13)
C6A—C7A	1.4550 (13)	C7B—H7BA	0.9300
C7A—H7AA	0.9300	C9B—H9BA	0.9600
C9A—H9AA	0.9600	C9B—H9BB	0.9600
C9A—H9AB	0.9600	C9B—H9BC	0.9600
C9A—H9AC	0.9600	O1W—H2W1	0.8600
S1B—C8B	1.7090 (10)	O1W—H1W1	0.8531
C2A—O1A—H1OA	109.5 (12)	C3B—O2B—C9B	115.87 (8)
C3A—O2A—C9A	117.44 (8)	C7B—N1B—N2B	114.34 (8)
C7A—N1A—N2A	115.51 (8)	C8B—N2B—N1B	120.11 (8)
C8A—N2A—N1A	118.54 (8)	C8B—N2B—H2NB	119.9 (11)
C8A—N2A—H2NA	123.0 (10)	N1B—N2B—H2NB	119.9 (11)
N1A—N2A—H2NA	118.2 (10)	C8B—N3B—H3NC	118.1 (11)
C8A—N3A—H3NA	120.0 (10)	C8B—N3B—H3ND	118.5 (10)
C8A—N3A—H3NB	122.4 (10)	H3NC—N3B—H3ND	122.8 (15)
H3NA—N3A—H3NB	117.6 (14)	C2B—C1B—C6B	120.65 (9)
C2A—C1A—C6A	119.93 (9)	C2B—C1B—H1BA	119.7
C2A—C1A—H1AA	120.0	C6B—C1B—H1BA	119.7
C6A—C1A—H1AA	120.0	O1B—C2B—C1B	118.58 (9)
C1A—C2A—O1A	119.54 (9)	O1B—C2B—C3B	121.76 (9)
C1A—C2A—C3A	120.63 (9)	C1B—C2B—C3B	119.67 (9)
O1A—C2A—C3A	119.82 (8)	O2B—C3B—C4B	125.42 (9)
O2A—C3A—C4A	126.57 (9)	O2B—C3B—C2B	114.74 (9)
O2A—C3A—C2A	113.56 (8)	C4B—C3B—C2B	119.84 (9)
C4A—C3A—C2A	119.86 (9)	C5B—C4B—C3B	120.41 (9)
C5A—C4A—C3A	119.55 (9)	C5B—C4B—H4BA	119.8
C5A—C4A—H4AA	120.2	C3B—C4B—H4BA	119.8
C3A—C4A—H4AA	120.2	C4B—C5B—C6B	120.01 (9)
C4A—C5A—C6A	120.79 (9)	C4B—C5B—H5BA	120.0
C4A—C5A—H5AA	119.6	C6B—C5B—H5BA	120.0
C6A—C5A—H5AA	119.6	C5B—C6B—C1B	119.39 (9)
C5A—C6A—C1A	119.24 (9)	C5B—C6B—C7B	122.48 (9)
C5A—C6A—C7A	122.91 (8)	C1B—C6B—C7B	118.13 (9)
C1A—C6A—C7A	117.85 (9)	N1B—C7B—C6B	121.82 (9)
N1A—C7A—C6A	121.12 (9)	N1B—C7B—H7BA	119.1
N1A—C7A—H7AA	119.4	C6B—C7B—H7BA	119.1
C6A—C7A—H7AA	119.4	N3B—C8B—N2B	118.02 (9)
N3A—C8A—N2A	117.23 (9)	N3B—C8B—S1B	123.94 (8)
N3A—C8A—S1A	123.10 (7)	N2B—C8B—S1B	118.01 (7)
N2A—C8A—S1A	119.64 (7)	O2B—C9B—H9BA	109.5
O2A—C9A—H9AA	109.5	O2B—C9B—H9BB	109.5
O2A—C9A—H9AB	109.5	H9BA—C9B—H9BB	109.5
H9AA—C9A—H9AB	109.5	O2B—C9B—H9BC	109.5
O2A—C9A—H9AC	109.5	H9BA—C9B—H9BC	109.5
H9AA—C9A—H9AC	109.5	H9BB—C9B—H9BC	109.5
H9AB—C9A—H9AC	109.5	H2W1—O1W—H1W1	109.0
C2B—O1B—H1OB	109.3 (12)
C7A—N1A—N2A—C8A	176.03 (9)	C7B—N1B—N2B—C8B	−175.36 (9)
C6A—C1A—C2A—O1A	−179.88 (9)	C6B—C1B—C2B—O1B	177.67 (9)
C6A—C1A—C2A—C3A	0.19 (15)	C6B—C1B—C2B—C3B	−1.69 (15)
C9A—O2A—C3A—C4A	−3.53 (16)	C9B—O2B—C3B—C4B	−1.14 (14)
C9A—O2A—C3A—C2A	177.37 (9)	C9B—O2B—C3B—C2B	178.05 (9)
C1A—C2A—C3A—O2A	179.06 (9)	O1B—C2B—C3B—O2B	1.74 (14)
O1A—C2A—C3A—O2A	−0.87 (14)	C1B—C2B—C3B—O2B	−178.92 (9)
C1A—C2A—C3A—C4A	−0.10 (15)	O1B—C2B—C3B—C4B	−179.02 (9)
O1A—C2A—C3A—C4A	179.97 (9)	C1B—C2B—C3B—C4B	0.33 (15)
O2A—C3A—C4A—C5A	−178.74 (10)	O2B—C3B—C4B—C5B	179.85 (9)
C2A—C3A—C4A—C5A	0.30 (15)	C2B—C3B—C4B—C5B	0.69 (15)
C3A—C4A—C5A—C6A	−0.61 (15)	C3B—C4B—C5B—C6B	−0.35 (15)
C4A—C5A—C6A—C1A	0.70 (15)	C4B—C5B—C6B—C1B	−1.00 (15)
C4A—C5A—C6A—C7A	−179.96 (10)	C4B—C5B—C6B—C7B	178.61 (9)
C2A—C1A—C6A—C5A	−0.49 (15)	C2B—C1B—C6B—C5B	2.03 (15)
C2A—C1A—C6A—C7A	−179.86 (9)	C2B—C1B—C6B—C7B	−177.59 (9)
N2A—N1A—C7A—C6A	179.81 (9)	N2B—N1B—C7B—C6B	−178.82 (9)
C5A—C6A—C7A—N1A	3.67 (16)	C5B—C6B—C7B—N1B	−3.38 (15)
C1A—C6A—C7A—N1A	−176.98 (9)	C1B—C6B—C7B—N1B	176.23 (9)
N1A—N2A—C8A—N3A	0.26 (14)	N1B—N2B—C8B—N3B	0.04 (14)
N1A—N2A—C8A—S1A	178.63 (7)	N1B—N2B—C8B—S1B	−178.29 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W1···S1B	0.86	2.28	3.1257 (9)	169
O1W—H1W1···O1Ai	0.85	1.95	2.7955 (12)	173
N2A—H2NA···S1Aii	0.929 (18)	2.450 (18)	3.3732 (9)	172.6 (18)
N2B—H2NB···S1Biii	0.842 (19)	2.571 (18)	3.4055 (10)	171.2 (18)
N3A—H3NA···N1A	0.847 (19)	2.258 (15)	2.6129 (14)	105.4 (12)
N3A—H3NB···O1Wiv	0.864 (16)	2.000 (15)	2.8408 (12)	164.0 (17)
N3B—H3NC···O1W	0.833 (19)	2.399 (19)	3.1492 (14)	150.2 (17)
N3B—H3ND···N1B	0.875 (19)	2.288 (17)	2.6554 (14)	105.2 (13)
O1A—H1OA···O2A	0.81 (2)	2.185 (18)	2.6292 (12)	114.5 (15)
O1B—H1OB···S1Av	0.82 (2)	2.685 (19)	3.2346 (10)	125.9 (16)
O1B—H1OB···O2B	0.82 (2)	2.251 (19)	2.6949 (13)	114.4 (16)
C1B—H1BA···O1Wvi	0.93	2.40	3.3140 (14)	169
C9B—H9BA···O2Avii	0.96	2.51	3.2286 (15)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W1⋯S1B	0.86	2.28	3.1257 (9)	169
O1W—H1W1⋯O1Ai	0.85	1.95	2.7955 (12)	173
N2A—H2NA⋯S1Aii	0.929 (18)	2.450 (18)	3.3732 (9)	172.6 (18)
N2B—H2NB⋯S1Biii	0.842 (19)	2.571 (18)	3.4055 (10)	171.2 (18)
N3A—H3NA⋯N1A	0.847 (19)	2.258 (15)	2.6129 (14)	105.4 (12)
N3A—H3NB⋯O1Wiv	0.864 (16)	2.000 (15)	2.8408 (12)	164.0 (17)
N3B—H3NC⋯O1W	0.833 (19)	2.399 (19)	3.1492 (14)	150.2 (17)
N3B—H3ND⋯N1B	0.875 (19)	2.288 (17)	2.6554 (14)	105.2 (13)
O1A—H1OA⋯O2A	0.81 (2)	2.185 (18)	2.6292 (12)	114.5 (15)
O1B—H1OB⋯S1Av	0.82 (2)	2.685 (19)	3.2346 (10)	125.9 (16)
O1B—H1OB⋯O2B	0.82 (2)	2.251 (19)	2.6949 (13)	114.4 (16)
C1B—H1BA⋯O1Wvi	0.93	2.40	3.3140 (14)	169
C9B—H9BA⋯O2Avii	0.96	2.51	3.2286 (15)	131

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