1-(2,3,4-Trihydroxy-benzyl-idene)thio-semicarbazide.

In the title mol-ecule, C(8)H(9)N(3)O(3)S, the thio-semicarbazide =N-NH-C(=S)-NH- fragment is twist a different degree of twist in the three independent mol-ecules [dihedral angles = 7.6 (1), 11.6 (1) and 20.7 (1)°]. Intra-molecular O-H⋯N and O-H⋯O hydrogen bonds occur. In the crystal, the hydr-oxy and amino groups are hydrogen-bond donors and the O-H⋯O, O-H⋯S and N-H⋯O hydrogen bonds generate a layer motif.

Related literature

For the crystal structures of 2,4-dihydroxy­benzaldehyde thio­semicarbazone and 3,4-dihydroxy­benzaldehyde thio­semi­carba­zone, see: Swesi et al. (2006 ▶); Tan et al. (2008 ▶).

Experimental

Crystal data

C8H9N3O3S

M = 227.24

Triclinic,

a = 10.3121 (10) Å

b = 11.8797 (12) Å

c = 12.4037 (12) Å

α = 68.969 (1)°

β = 87.487 (1)°

γ = 77.161 (1)°

V = 1381.8 (2) Å3

Z = 6

Mo Kα radiation

μ = 0.34 mm−1

T = 100 K

0.35 × 0.10 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.890, T max = 0.993

13248 measured reflections

6327 independent reflections

4487 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.114

S = 1.02

6327 reflections

478 parameters

18 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810015850/pk2242sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810015850/pk2242Isup2.hkl

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

C8H9N3O3S	Z = 6
Mr = 227.24	F(000) = 708
Triclinic, P1	Dx = 1.639 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.3121 (10) Å	Cell parameters from 2924 reflections
b = 11.8797 (12) Å	θ = 2.6–28.1°
c = 12.4037 (12) Å	µ = 0.34 mm−1
α = 68.969 (1)°	T = 100 K
β = 87.487 (1)°	Plate, pale brown
γ = 77.161 (1)°	0.35 × 0.10 × 0.02 mm
V = 1381.8 (2) Å3

Bruker SMART APEX diffractometer	6327 independent reflections
Radiation source: fine-focus sealed tube	4487 reflections with I > 2σ(I)
graphite	Rint = 0.033
ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→12
Tmin = 0.890, Tmax = 0.993	k = −15→15
13248 measured reflections	l = −16→16

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0572P)2 + 0.0368P] where P = (Fo2 + 2Fc2)/3
6327 reflections	(Δ/σ)max < 0.001
478 parameters	Δρmax = 0.38 e Å−3
18 restraints	Δρmin = −0.37 e Å−3

	x	y	z	Uiso*/Ueq
S1	0.04483 (6)	0.85739 (5)	0.67520 (4)	0.01600 (14)
S2	0.39952 (6)	0.72567 (5)	0.55744 (5)	0.01715 (14)
S3	0.32855 (6)	1.02438 (5)	0.19484 (5)	0.01889 (15)
O1	0.02467 (17)	0.58729 (14)	0.32793 (12)	0.0171 (4)
H1	0.030 (3)	0.622 (2)	0.3749 (19)	0.033 (8)*
O2	−0.01767 (17)	0.52286 (14)	0.14650 (13)	0.0185 (4)
H2	0.023 (3)	0.489 (3)	0.103 (2)	0.048 (10)*
O3	0.00587 (16)	0.67307 (14)	−0.07208 (12)	0.0165 (3)
H3	0.019 (3)	0.725 (2)	−0.1352 (14)	0.031 (8)*
O4	0.30904 (16)	0.48727 (14)	0.20588 (12)	0.0159 (3)
H4	0.325 (3)	0.514 (3)	0.257 (2)	0.054 (10)*
O5	0.23954 (17)	0.43594 (14)	0.02850 (13)	0.0180 (4)
H5	0.218 (3)	0.438 (3)	−0.0364 (14)	0.063 (11)*
O6	0.30786 (16)	0.55735 (14)	−0.19098 (13)	0.0166 (3)
H6	0.326 (3)	0.607 (2)	−0.2539 (13)	0.030 (8)*
O7	0.27294 (17)	1.30858 (14)	0.54062 (13)	0.0184 (4)
H7	0.287 (3)	1.270 (2)	0.496 (2)	0.038 (9)*
O8	0.27623 (17)	1.38726 (14)	0.71552 (13)	0.0182 (4)
H8	0.284 (3)	1.399 (3)	0.7771 (16)	0.051 (10)*
O9	0.28539 (16)	1.23273 (14)	0.93746 (12)	0.0168 (3)
H9	0.294 (3)	1.1754 (17)	1.0024 (12)	0.025 (7)*
N1	0.05073 (18)	0.77060 (16)	0.39755 (14)	0.0124 (4)
N2	0.05168 (19)	0.83290 (16)	0.47275 (15)	0.0131 (4)
H21	0.045 (2)	0.9116 (10)	0.445 (2)	0.024 (7)*
N3	0.0408 (2)	0.65715 (17)	0.62610 (16)	0.0194 (4)
H31	0.033 (3)	0.620 (2)	0.6981 (10)	0.036 (8)*
H32	0.038 (2)	0.6192 (19)	0.5797 (17)	0.018 (7)*
N4	0.39153 (18)	0.64797 (15)	0.27613 (15)	0.0126 (4)
N5	0.40933 (19)	0.70383 (17)	0.35334 (15)	0.0135 (4)
H51	0.425 (3)	0.7772 (14)	0.324 (2)	0.045 (9)*
N6	0.3389 (2)	0.54900 (17)	0.49721 (16)	0.0177 (4)
H61	0.325 (2)	0.510 (2)	0.5681 (10)	0.020 (7)*
H62	0.334 (2)	0.515 (2)	0.4482 (16)	0.019 (7)*
N7	0.30054 (19)	1.11133 (16)	0.47366 (15)	0.0153 (4)
N8	0.3167 (2)	1.04604 (17)	0.39915 (15)	0.0163 (4)
H81	0.337 (2)	0.9667 (9)	0.425 (2)	0.019 (7)*
N9	0.2893 (2)	1.22846 (17)	0.24562 (16)	0.0200 (4)
H91	0.284 (2)	1.270 (2)	0.1728 (9)	0.024 (7)*
H92	0.278 (3)	1.265 (2)	0.2949 (18)	0.034 (8)*
C1	0.0359 (2)	0.66793 (19)	0.21952 (17)	0.0121 (4)
C2	0.0183 (2)	0.63384 (18)	0.12652 (18)	0.0129 (4)
C3	0.0300 (2)	0.71265 (19)	0.01372 (17)	0.0123 (4)
C4	0.0646 (2)	0.82510 (19)	−0.00648 (18)	0.0139 (5)
H4A	0.0770	0.8772	−0.0829	0.017*
C5	0.0806 (2)	0.85971 (19)	0.08633 (17)	0.0129 (4)
H5A	0.1033	0.9368	0.0726	0.015*
C6	0.0645 (2)	0.78427 (19)	0.19995 (17)	0.0117 (4)
C7	0.0709 (2)	0.83158 (19)	0.29141 (17)	0.0123 (4)
H7A	0.0908	0.9106	0.2726	0.015*
C8	0.0451 (2)	0.77519 (19)	0.58732 (18)	0.0136 (5)
C9	0.3408 (2)	0.55759 (19)	0.09885 (17)	0.0125 (4)
C10	0.3076 (2)	0.52858 (18)	0.00573 (18)	0.0129 (4)
C11	0.3422 (2)	0.59381 (19)	−0.10491 (17)	0.0120 (4)
C12	0.4069 (2)	0.68949 (19)	−0.12458 (18)	0.0138 (5)
H12	0.4322	0.7323	−0.2002	0.017*
C13	0.4343 (2)	0.72205 (19)	−0.03270 (18)	0.0135 (4)
H13	0.4767	0.7889	−0.0463	0.016*
C14	0.4006 (2)	0.65829 (19)	0.07964 (17)	0.0119 (4)
C15	0.4214 (2)	0.70176 (19)	0.17123 (18)	0.0126 (4)
H15	0.4584	0.7725	0.1532	0.015*
C16	0.3804 (2)	0.65349 (19)	0.46518 (18)	0.0130 (4)
C17	0.2798 (2)	1.22282 (19)	0.64927 (18)	0.0135 (4)
C18	0.2795 (2)	1.26454 (19)	0.74128 (18)	0.0134 (5)
C19	0.2838 (2)	1.1822 (2)	0.85449 (18)	0.0134 (4)
C20	0.2863 (2)	1.0579 (2)	0.87772 (18)	0.0152 (5)
H20	0.2871	1.0021	0.9551	0.018*
C21	0.2877 (2)	1.0171 (2)	0.78646 (18)	0.0153 (5)
H21a	0.2898	0.9324	0.8020	0.018*
C22	0.2860 (2)	1.09729 (19)	0.67167 (18)	0.0133 (4)
C23	0.2966 (2)	1.0449 (2)	0.58130 (18)	0.0146 (5)
H23	0.3008	0.9590	0.6023	0.018*
C24	0.3104 (2)	1.1070 (2)	0.28385 (18)	0.0149 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0281 (4)	0.0122 (3)	0.0102 (2)	−0.0063 (2)	0.0013 (2)	−0.0060 (2)
S2	0.0270 (4)	0.0164 (3)	0.0125 (3)	−0.0084 (2)	0.0028 (2)	−0.0086 (2)
S3	0.0312 (4)	0.0155 (3)	0.0128 (3)	−0.0074 (2)	0.0010 (2)	−0.0070 (2)
O1	0.0326 (10)	0.0128 (8)	0.0088 (7)	−0.0099 (7)	0.0009 (7)	−0.0042 (6)
O2	0.0340 (11)	0.0120 (8)	0.0157 (8)	−0.0124 (7)	0.0038 (7)	−0.0083 (6)
O3	0.0283 (10)	0.0156 (8)	0.0096 (7)	−0.0104 (7)	0.0011 (7)	−0.0059 (6)
O4	0.0279 (10)	0.0134 (8)	0.0093 (7)	−0.0097 (7)	0.0017 (6)	−0.0046 (6)
O5	0.0321 (10)	0.0160 (8)	0.0105 (7)	−0.0138 (7)	−0.0001 (7)	−0.0052 (6)
O6	0.0286 (10)	0.0147 (8)	0.0097 (7)	−0.0082 (7)	0.0000 (7)	−0.0061 (6)
O7	0.0345 (11)	0.0124 (8)	0.0108 (7)	−0.0075 (7)	0.0019 (7)	−0.0060 (6)
O8	0.0319 (10)	0.0132 (8)	0.0141 (8)	−0.0097 (7)	0.0035 (7)	−0.0079 (6)
O9	0.0257 (10)	0.0178 (8)	0.0099 (7)	−0.0080 (7)	0.0008 (7)	−0.0066 (6)
N1	0.0151 (10)	0.0125 (9)	0.0122 (9)	−0.0039 (7)	−0.0017 (7)	−0.0068 (7)
N2	0.0222 (11)	0.0088 (9)	0.0109 (8)	−0.0041 (8)	−0.0001 (7)	−0.0063 (7)
N3	0.0399 (13)	0.0113 (9)	0.0096 (9)	−0.0090 (9)	−0.0003 (9)	−0.0047 (7)
N4	0.0171 (10)	0.0107 (9)	0.0128 (9)	−0.0025 (7)	−0.0020 (7)	−0.0075 (7)
N5	0.0200 (11)	0.0111 (9)	0.0135 (9)	−0.0057 (8)	0.0003 (7)	−0.0079 (7)
N6	0.0321 (12)	0.0126 (9)	0.0107 (9)	−0.0083 (8)	0.0021 (8)	−0.0049 (8)
N7	0.0226 (11)	0.0114 (9)	0.0154 (9)	−0.0053 (8)	0.0004 (8)	−0.0082 (7)
N8	0.0303 (12)	0.0092 (9)	0.0117 (9)	−0.0059 (8)	0.0005 (8)	−0.0056 (7)
N9	0.0373 (13)	0.0114 (9)	0.0119 (9)	−0.0077 (9)	−0.0011 (9)	−0.0034 (8)
C1	0.0140 (12)	0.0109 (10)	0.0107 (10)	−0.0023 (8)	0.0013 (8)	−0.0035 (8)
C2	0.0151 (12)	0.0091 (10)	0.0156 (10)	−0.0040 (8)	0.0003 (9)	−0.0048 (8)
C3	0.0131 (12)	0.0138 (10)	0.0118 (10)	−0.0033 (9)	0.0002 (8)	−0.0065 (8)
C4	0.0166 (12)	0.0126 (10)	0.0109 (10)	−0.0040 (9)	0.0014 (8)	−0.0018 (8)
C5	0.0161 (12)	0.0087 (10)	0.0146 (10)	−0.0035 (8)	−0.0004 (8)	−0.0044 (8)
C6	0.0117 (11)	0.0104 (10)	0.0137 (10)	−0.0022 (8)	−0.0005 (8)	−0.0051 (8)
C7	0.0132 (12)	0.0102 (10)	0.0143 (10)	−0.0039 (8)	−0.0018 (8)	−0.0044 (8)
C8	0.0165 (12)	0.0136 (10)	0.0121 (10)	−0.0044 (9)	0.0006 (8)	−0.0056 (8)
C9	0.0150 (12)	0.0112 (10)	0.0104 (9)	−0.0009 (8)	0.0011 (8)	−0.0040 (8)
C10	0.0169 (12)	0.0077 (10)	0.0150 (10)	−0.0043 (9)	0.0004 (8)	−0.0042 (8)
C11	0.0161 (12)	0.0107 (10)	0.0109 (10)	−0.0014 (8)	−0.0020 (8)	−0.0064 (8)
C12	0.0165 (12)	0.0125 (10)	0.0124 (10)	−0.0039 (9)	0.0015 (8)	−0.0041 (8)
C13	0.0132 (12)	0.0111 (10)	0.0156 (10)	−0.0022 (8)	−0.0016 (8)	−0.0040 (8)
C14	0.0135 (12)	0.0105 (10)	0.0129 (10)	−0.0018 (8)	−0.0020 (8)	−0.0056 (8)
C15	0.0138 (12)	0.0108 (10)	0.0144 (10)	−0.0021 (8)	−0.0016 (8)	−0.0059 (8)
C16	0.0143 (12)	0.0113 (10)	0.0128 (10)	−0.0006 (9)	−0.0007 (8)	−0.0046 (8)
C17	0.0160 (12)	0.0123 (10)	0.0116 (10)	−0.0041 (9)	0.0001 (8)	−0.0031 (8)
C18	0.0163 (12)	0.0120 (10)	0.0148 (10)	−0.0057 (9)	0.0017 (9)	−0.0067 (8)
C19	0.0118 (12)	0.0181 (11)	0.0134 (10)	−0.0050 (9)	0.0033 (8)	−0.0085 (9)
C20	0.0179 (13)	0.0149 (11)	0.0112 (10)	−0.0045 (9)	0.0011 (9)	−0.0025 (8)
C21	0.0202 (13)	0.0102 (10)	0.0161 (11)	−0.0048 (9)	0.0007 (9)	−0.0044 (8)
C22	0.0148 (12)	0.0125 (10)	0.0145 (10)	−0.0045 (9)	0.0005 (8)	−0.0063 (8)
C23	0.0171 (12)	0.0123 (10)	0.0165 (11)	−0.0046 (9)	−0.0007 (9)	−0.0066 (9)
C24	0.0174 (12)	0.0155 (11)	0.0136 (10)	−0.0068 (9)	0.0002 (9)	−0.0052 (9)

S1—C8	1.704 (2)	N7—N8	1.388 (2)
S2—C16	1.698 (2)	N8—C24	1.348 (3)
S3—C24	1.702 (2)	N8—H81	0.858 (10)
O1—C1	1.360 (2)	N9—C24	1.316 (3)
O1—H1	0.836 (10)	N9—H91	0.857 (10)
O2—C2	1.383 (2)	N9—H92	0.861 (10)
O2—H2	0.834 (10)	C1—C2	1.383 (3)
O3—C3	1.360 (2)	C1—C6	1.411 (3)
O3—H3	0.833 (10)	C2—C3	1.394 (3)
O4—C9	1.362 (2)	C3—C4	1.392 (3)
O4—H4	0.835 (10)	C4—C5	1.381 (3)
O5—C10	1.374 (2)	C4—H4A	0.9500
O5—H5	0.831 (10)	C5—C6	1.399 (3)
O6—C11	1.373 (2)	C5—H5A	0.9500
O6—H6	0.835 (10)	C6—C7	1.445 (3)
O7—C17	1.360 (2)	C7—H7A	0.9500
O7—H7	0.830 (10)	C9—C10	1.394 (3)
O8—C18	1.369 (2)	C9—C14	1.406 (3)
O8—H8	0.837 (10)	C10—C11	1.389 (3)
O9—C19	1.367 (2)	C11—C12	1.385 (3)
O9—H9	0.840 (10)	C12—C13	1.386 (3)
N1—C7	1.288 (3)	C12—H12	0.9500
N1—N2	1.385 (2)	C13—C14	1.398 (3)
N2—C8	1.344 (3)	C13—H13	0.9500
N2—H21	0.860 (10)	C14—C15	1.447 (3)
N3—C8	1.320 (3)	C15—H15	0.9500
N3—H31	0.851 (10)	C17—C18	1.398 (3)
N3—H32	0.853 (10)	C17—C22	1.402 (3)
N4—C15	1.285 (3)	C18—C19	1.390 (3)
N4—N5	1.385 (2)	C19—C20	1.394 (3)
N5—C16	1.349 (3)	C20—C21	1.380 (3)
N5—H51	0.865 (10)	C20—H20	0.9500
N6—C16	1.323 (3)	C21—C22	1.399 (3)
N6—H61	0.858 (10)	C21—H21a	0.9500
N6—H62	0.849 (10)	C22—C23	1.454 (3)
N7—C23	1.288 (3)	C23—H23	0.9500
C1—O1—H1	108.4 (19)	N3—C8—N2	118.19 (19)
C2—O2—H2	110 (2)	N3—C8—S1	123.33 (16)
C3—O3—H3	108.4 (19)	N2—C8—S1	118.47 (16)
C9—O4—H4	112 (2)	O4—C9—C10	117.13 (19)
C10—O5—H5	104 (2)	O4—C9—C14	122.83 (19)
C11—O6—H6	107.5 (19)	C10—C9—C14	120.01 (19)
C17—O7—H7	106 (2)	O5—C10—C11	122.75 (19)
C18—O8—H8	109 (2)	O5—C10—C9	117.48 (19)
C19—O9—H9	108.1 (18)	C11—C10—C9	119.76 (19)
C7—N1—N2	114.97 (17)	O6—C11—C12	123.38 (19)
C8—N2—N1	120.71 (17)	O6—C11—C10	115.75 (19)
C8—N2—H21	119.4 (17)	C12—C11—C10	120.87 (19)
N1—N2—H21	119.2 (17)	C13—C12—C11	119.3 (2)
C8—N3—H31	119.2 (19)	C13—C12—H12	120.3
C8—N3—H32	121.1 (16)	C11—C12—H12	120.3
H31—N3—H32	119 (2)	C12—C13—C14	121.2 (2)
C15—N4—N5	116.06 (18)	C12—C13—H13	119.4
C16—N5—N4	119.95 (18)	C14—C13—H13	119.4
C16—N5—H51	122.7 (19)	C13—C14—C9	118.70 (19)
N4—N5—H51	116.4 (19)	C13—C14—C15	119.20 (19)
C16—N6—H61	121.8 (17)	C9—C14—C15	122.01 (19)
C16—N6—H62	119.6 (17)	N4—C15—C14	122.3 (2)
H61—N6—H62	118 (2)	N4—C15—H15	118.9
C23—N7—N8	114.78 (18)	C14—C15—H15	118.9
C24—N8—N7	120.06 (18)	N6—C16—N5	117.59 (19)
C24—N8—H81	118.3 (16)	N6—C16—S2	123.38 (16)
N7—N8—H81	121.4 (16)	N5—C16—S2	119.03 (16)
C24—N9—H91	120.2 (17)	O7—C17—C18	117.13 (19)
C24—N9—H92	118.8 (18)	O7—C17—C22	123.12 (19)
H91—N9—H92	121 (2)	C18—C17—C22	119.74 (19)
O1—C1—C2	118.45 (19)	O8—C18—C19	122.09 (19)
O1—C1—C6	121.89 (18)	O8—C18—C17	117.80 (18)
C2—C1—C6	119.65 (19)	C19—C18—C17	120.11 (19)
O2—C2—C1	119.04 (18)	O9—C19—C18	115.08 (19)
O2—C2—C3	120.19 (18)	O9—C19—C20	124.29 (19)
C1—C2—C3	120.69 (19)	C18—C19—C20	120.6 (2)
O3—C3—C4	123.43 (18)	C21—C20—C19	118.9 (2)
O3—C3—C2	116.36 (18)	C21—C20—H20	120.5
C4—C3—C2	120.20 (19)	C19—C20—H20	120.5
C5—C4—C3	119.01 (19)	C20—C21—C22	121.8 (2)
C5—C4—H4A	120.5	C20—C21—H21a	119.1
C3—C4—H4A	120.5	C22—C21—H21a	119.1
C4—C5—C6	121.78 (19)	C21—C22—C17	118.79 (19)
C4—C5—H5A	119.1	C21—C22—C23	118.05 (19)
C6—C5—H5A	119.1	C17—C22—C23	123.11 (19)
C5—C6—C1	118.54 (19)	N7—C23—C22	122.12 (19)
C5—C6—C7	118.53 (19)	N7—C23—H23	118.9
C1—C6—C7	122.85 (19)	C22—C23—H23	118.9
N1—C7—C6	122.49 (19)	N9—C24—N8	118.0 (2)
N1—C7—H7A	118.8	N9—C24—S3	123.12 (17)
C6—C7—H7A	118.8	N8—C24—S3	118.90 (16)
C7—N1—N2—C8	−173.3 (2)	C11—C12—C13—C14	1.5 (3)
C15—N4—N5—C16	179.99 (19)	C12—C13—C14—C9	1.6 (3)
C23—N7—N8—C24	174.1 (2)	C12—C13—C14—C15	−175.1 (2)
O1—C1—C2—O2	3.8 (3)	O4—C9—C14—C13	177.55 (19)
C6—C1—C2—O2	−176.09 (19)	C10—C9—C14—C13	−4.6 (3)
O1—C1—C2—C3	−179.37 (19)	O4—C9—C14—C15	−5.9 (3)
C6—C1—C2—C3	0.8 (3)	C10—C9—C14—C15	172.0 (2)
O2—C2—C3—O3	−0.7 (3)	N5—N4—C15—C14	−176.27 (18)
C1—C2—C3—O3	−177.53 (19)	C13—C14—C15—N4	179.4 (2)
O2—C2—C3—C4	179.20 (19)	C9—C14—C15—N4	2.9 (3)
C1—C2—C3—C4	2.4 (3)	N4—N5—C16—N6	1.8 (3)
O3—C3—C4—C5	176.8 (2)	N4—N5—C16—S2	−178.53 (15)
C2—C3—C4—C5	−3.1 (3)	O7—C17—C18—O8	−1.8 (3)
C3—C4—C5—C6	0.7 (3)	C22—C17—C18—O8	178.62 (19)
C4—C5—C6—C1	2.4 (3)	O7—C17—C18—C19	178.8 (2)
C4—C5—C6—C7	−174.4 (2)	C22—C17—C18—C19	−0.8 (3)
O1—C1—C6—C5	177.06 (19)	O8—C18—C19—O9	−0.4 (3)
C2—C1—C6—C5	−3.1 (3)	C17—C18—C19—O9	178.91 (19)
O1—C1—C6—C7	−6.3 (3)	O8—C18—C19—C20	179.7 (2)
C2—C1—C6—C7	173.6 (2)	C17—C18—C19—C20	−1.0 (3)
N2—N1—C7—C6	−175.78 (18)	O9—C19—C20—C21	−178.4 (2)
C5—C6—C7—N1	176.6 (2)	C18—C19—C20—C21	1.5 (3)
C1—C6—C7—N1	−0.1 (3)	C19—C20—C21—C22	−0.3 (3)
N1—N2—C8—N3	1.5 (3)	C20—C21—C22—C17	−1.4 (3)
N1—N2—C8—S1	−179.28 (15)	C20—C21—C22—C23	176.0 (2)
O4—C9—C10—O5	3.3 (3)	O7—C17—C22—C21	−177.6 (2)
C14—C9—C10—O5	−174.69 (19)	C18—C17—C22—C21	1.9 (3)
O4—C9—C10—C11	−177.45 (18)	O7—C17—C22—C23	5.2 (4)
C14—C9—C10—C11	4.5 (3)	C18—C17—C22—C23	−175.3 (2)
O5—C10—C11—O6	−2.0 (3)	N8—N7—C23—C22	177.28 (19)
C9—C10—C11—O6	178.77 (19)	C21—C22—C23—N7	−177.5 (2)
O5—C10—C11—C12	177.7 (2)	C17—C22—C23—N7	−0.3 (4)
C9—C10—C11—C12	−1.5 (3)	N7—N8—C24—N9	0.3 (3)
O6—C11—C12—C13	178.2 (2)	N7—N8—C24—S3	−179.20 (16)
C10—C11—C12—C13	−1.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.84 (1)	1.94 (2)	2.682 (2)	147 (3)
O2—H2···O3i	0.83 (1)	2.17 (2)	2.773 (2)	129 (3)
O3—H3···S1ii	0.83 (1)	2.36 (1)	3.184 (2)	173 (3)
O4—H4···N4	0.84 (1)	1.96 (2)	2.666 (2)	141 (3)
O5—H5···O6	0.83 (1)	2.24 (3)	2.730 (2)	118 (3)
O6—H6···S2ii	0.84 (1)	2.45 (1)	3.276 (2)	172 (2)
O7—H7···N7	0.83 (1)	1.97 (2)	2.710 (2)	148 (3)
O8—H8···O9	0.84 (1)	2.24 (3)	2.697 (2)	114 (2)
O9—H9···S3iii	0.84 (1)	2.40 (1)	3.237 (2)	174 (2)
N3—H31···O2iv	0.85 (1)	2.09 (1)	2.902 (2)	159 (3)
N6—H61···O8v	0.86 (1)	2.01 (1)	2.847 (2)	164 (2)
N9—H91···O5vi	0.86 (1)	2.11 (2)	2.896 (2)	153 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.84 (1)	1.94 (2)	2.682 (2)	147 (3)
O2—H2⋯O3i	0.83 (1)	2.17 (2)	2.773 (2)	129 (3)
O3—H3⋯S1ii	0.83 (1)	2.36 (1)	3.184 (2)	173 (3)
O4—H4⋯N4	0.84 (1)	1.96 (2)	2.666 (2)	141 (3)
O5—H5⋯O6	0.83 (1)	2.24 (3)	2.730 (2)	118 (3)
O6—H6⋯S2ii	0.84 (1)	2.45 (1)	3.276 (2)	172 (2)
O7—H7⋯N7	0.83 (1)	1.97 (2)	2.710 (2)	148 (3)
O8—H8⋯O9	0.84 (1)	2.24 (3)	2.697 (2)	114 (2)
O9—H9⋯S3iii	0.84 (1)	2.40 (1)	3.237 (2)	174 (2)
N3—H31⋯O2iv	0.85 (1)	2.09 (1)	2.902 (2)	159 (3)
N6—H61⋯O8v	0.86 (1)	2.01 (1)	2.847 (2)	164 (2)
N9—H91⋯O5vi	0.86 (1)	2.11 (2)	2.896 (2)	153 (2)

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