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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1278.
Published online 2010 May 8. doi:  10.1107/S1600536810015850
PMCID: PMC2979487

1-(2,3,4-Trihydroxy­benzyl­idene)thio­semicarbazide

Abstract

In the title mol­ecule, C8H9N3O3S, the thio­semicarbazide =N—NH—C(=S)—NH— fragment is twist a different degree of twist in the three independent mol­ecules [dihedral angles = 7.6 (1), 11.6 (1) and 20.7 (1)°]. Intra­molecular O—H(...)N and O—H(...)O hydrogen bonds occur. In the crystal, the hydr­oxy 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 [triangle]); Tan et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1278-scheme1.jpg

Experimental

Crystal data

  • C8H9N3O3S
  • M r = 227.24
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1278-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

We thank the University of Malaya (PS354/2009) and MOHE (FRGS-FP001/2009) for supporting this study. HBS thanks the Libyan People’s Bureau in Malaysia for a scholarship.

supplementary crystallographic information

Experimental

2,3,4-Trihydroxybenzaldehyde (1.54 g, 10 mmol) and thiosemicarbazide (0.91 g, 1 mmol) were heated in ethanol (20 ml). The cool solution was set aside for the growth of crystals.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 or 1.5U(CMe).

The amino and hydroxy H-atoms were located in a difference Fourier map, and were refined with distance restraints of N–H 0.86 (1) and O–H 0.84 (1) Å; their temperature factors were freely refined.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the three independent molecules of C8H9N3O3S at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C8H9N3O3SZ = 6
Mr = 227.24F(000) = 708
Triclinic, P1Dx = 1.639 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.3121 (10) ÅCell parameters from 2924 reflections
b = 11.8797 (12) Åθ = 2.6–28.1°
c = 12.4037 (12) ŵ = 0.34 mm1
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

Data collection

Bruker SMART APEX diffractometer6327 independent reflections
Radiation source: fine-focus sealed tube4487 reflections with I > 2σ(I)
graphiteRint = 0.033
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→12
Tmin = 0.890, Tmax = 0.993k = −15→15
13248 measured reflectionsl = −16→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0572P)2 + 0.0368P] where P = (Fo2 + 2Fc2)/3
6327 reflections(Δ/σ)max < 0.001
478 parametersΔρmax = 0.38 e Å3
18 restraintsΔρmin = −0.37 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.04483 (6)0.85739 (5)0.67520 (4)0.01600 (14)
S20.39952 (6)0.72567 (5)0.55744 (5)0.01715 (14)
S30.32855 (6)1.02438 (5)0.19484 (5)0.01889 (15)
O10.02467 (17)0.58729 (14)0.32793 (12)0.0171 (4)
H10.030 (3)0.622 (2)0.3749 (19)0.033 (8)*
O2−0.01767 (17)0.52286 (14)0.14650 (13)0.0185 (4)
H20.023 (3)0.489 (3)0.103 (2)0.048 (10)*
O30.00587 (16)0.67307 (14)−0.07208 (12)0.0165 (3)
H30.019 (3)0.725 (2)−0.1352 (14)0.031 (8)*
O40.30904 (16)0.48727 (14)0.20588 (12)0.0159 (3)
H40.325 (3)0.514 (3)0.257 (2)0.054 (10)*
O50.23954 (17)0.43594 (14)0.02850 (13)0.0180 (4)
H50.218 (3)0.438 (3)−0.0364 (14)0.063 (11)*
O60.30786 (16)0.55735 (14)−0.19098 (13)0.0166 (3)
H60.326 (3)0.607 (2)−0.2539 (13)0.030 (8)*
O70.27294 (17)1.30858 (14)0.54062 (13)0.0184 (4)
H70.287 (3)1.270 (2)0.496 (2)0.038 (9)*
O80.27623 (17)1.38726 (14)0.71552 (13)0.0182 (4)
H80.284 (3)1.399 (3)0.7771 (16)0.051 (10)*
O90.28539 (16)1.23273 (14)0.93746 (12)0.0168 (3)
H90.294 (3)1.1754 (17)1.0024 (12)0.025 (7)*
N10.05073 (18)0.77060 (16)0.39755 (14)0.0124 (4)
N20.05168 (19)0.83290 (16)0.47275 (15)0.0131 (4)
H210.045 (2)0.9116 (10)0.445 (2)0.024 (7)*
N30.0408 (2)0.65715 (17)0.62610 (16)0.0194 (4)
H310.033 (3)0.620 (2)0.6981 (10)0.036 (8)*
H320.038 (2)0.6192 (19)0.5797 (17)0.018 (7)*
N40.39153 (18)0.64797 (15)0.27613 (15)0.0126 (4)
N50.40933 (19)0.70383 (17)0.35334 (15)0.0135 (4)
H510.425 (3)0.7772 (14)0.324 (2)0.045 (9)*
N60.3389 (2)0.54900 (17)0.49721 (16)0.0177 (4)
H610.325 (2)0.510 (2)0.5681 (10)0.020 (7)*
H620.334 (2)0.515 (2)0.4482 (16)0.019 (7)*
N70.30054 (19)1.11133 (16)0.47366 (15)0.0153 (4)
N80.3167 (2)1.04604 (17)0.39915 (15)0.0163 (4)
H810.337 (2)0.9667 (9)0.425 (2)0.019 (7)*
N90.2893 (2)1.22846 (17)0.24562 (16)0.0200 (4)
H910.284 (2)1.270 (2)0.1728 (9)0.024 (7)*
H920.278 (3)1.265 (2)0.2949 (18)0.034 (8)*
C10.0359 (2)0.66793 (19)0.21952 (17)0.0121 (4)
C20.0183 (2)0.63384 (18)0.12652 (18)0.0129 (4)
C30.0300 (2)0.71265 (19)0.01372 (17)0.0123 (4)
C40.0646 (2)0.82510 (19)−0.00648 (18)0.0139 (5)
H4A0.07700.8772−0.08290.017*
C50.0806 (2)0.85971 (19)0.08633 (17)0.0129 (4)
H5A0.10330.93680.07260.015*
C60.0645 (2)0.78427 (19)0.19995 (17)0.0117 (4)
C70.0709 (2)0.83158 (19)0.29141 (17)0.0123 (4)
H7A0.09080.91060.27260.015*
C80.0451 (2)0.77519 (19)0.58732 (18)0.0136 (5)
C90.3408 (2)0.55759 (19)0.09885 (17)0.0125 (4)
C100.3076 (2)0.52858 (18)0.00573 (18)0.0129 (4)
C110.3422 (2)0.59381 (19)−0.10491 (17)0.0120 (4)
C120.4069 (2)0.68949 (19)−0.12458 (18)0.0138 (5)
H120.43220.7323−0.20020.017*
C130.4343 (2)0.72205 (19)−0.03270 (18)0.0135 (4)
H130.47670.7889−0.04630.016*
C140.4006 (2)0.65829 (19)0.07964 (17)0.0119 (4)
C150.4214 (2)0.70176 (19)0.17123 (18)0.0126 (4)
H150.45840.77250.15320.015*
C160.3804 (2)0.65349 (19)0.46518 (18)0.0130 (4)
C170.2798 (2)1.22282 (19)0.64927 (18)0.0135 (4)
C180.2795 (2)1.26454 (19)0.74128 (18)0.0134 (5)
C190.2838 (2)1.1822 (2)0.85449 (18)0.0134 (4)
C200.2863 (2)1.0579 (2)0.87772 (18)0.0152 (5)
H200.28711.00210.95510.018*
C210.2877 (2)1.0171 (2)0.78646 (18)0.0153 (5)
H21a0.28980.93240.80200.018*
C220.2860 (2)1.09729 (19)0.67167 (18)0.0133 (4)
C230.2966 (2)1.0449 (2)0.58130 (18)0.0146 (5)
H230.30080.95900.60230.018*
C240.3104 (2)1.1070 (2)0.28385 (18)0.0149 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0281 (4)0.0122 (3)0.0102 (2)−0.0063 (2)0.0013 (2)−0.0060 (2)
S20.0270 (4)0.0164 (3)0.0125 (3)−0.0084 (2)0.0028 (2)−0.0086 (2)
S30.0312 (4)0.0155 (3)0.0128 (3)−0.0074 (2)0.0010 (2)−0.0070 (2)
O10.0326 (10)0.0128 (8)0.0088 (7)−0.0099 (7)0.0009 (7)−0.0042 (6)
O20.0340 (11)0.0120 (8)0.0157 (8)−0.0124 (7)0.0038 (7)−0.0083 (6)
O30.0283 (10)0.0156 (8)0.0096 (7)−0.0104 (7)0.0011 (7)−0.0059 (6)
O40.0279 (10)0.0134 (8)0.0093 (7)−0.0097 (7)0.0017 (6)−0.0046 (6)
O50.0321 (10)0.0160 (8)0.0105 (7)−0.0138 (7)−0.0001 (7)−0.0052 (6)
O60.0286 (10)0.0147 (8)0.0097 (7)−0.0082 (7)0.0000 (7)−0.0061 (6)
O70.0345 (11)0.0124 (8)0.0108 (7)−0.0075 (7)0.0019 (7)−0.0060 (6)
O80.0319 (10)0.0132 (8)0.0141 (8)−0.0097 (7)0.0035 (7)−0.0079 (6)
O90.0257 (10)0.0178 (8)0.0099 (7)−0.0080 (7)0.0008 (7)−0.0066 (6)
N10.0151 (10)0.0125 (9)0.0122 (9)−0.0039 (7)−0.0017 (7)−0.0068 (7)
N20.0222 (11)0.0088 (9)0.0109 (8)−0.0041 (8)−0.0001 (7)−0.0063 (7)
N30.0399 (13)0.0113 (9)0.0096 (9)−0.0090 (9)−0.0003 (9)−0.0047 (7)
N40.0171 (10)0.0107 (9)0.0128 (9)−0.0025 (7)−0.0020 (7)−0.0075 (7)
N50.0200 (11)0.0111 (9)0.0135 (9)−0.0057 (8)0.0003 (7)−0.0079 (7)
N60.0321 (12)0.0126 (9)0.0107 (9)−0.0083 (8)0.0021 (8)−0.0049 (8)
N70.0226 (11)0.0114 (9)0.0154 (9)−0.0053 (8)0.0004 (8)−0.0082 (7)
N80.0303 (12)0.0092 (9)0.0117 (9)−0.0059 (8)0.0005 (8)−0.0056 (7)
N90.0373 (13)0.0114 (9)0.0119 (9)−0.0077 (9)−0.0011 (9)−0.0034 (8)
C10.0140 (12)0.0109 (10)0.0107 (10)−0.0023 (8)0.0013 (8)−0.0035 (8)
C20.0151 (12)0.0091 (10)0.0156 (10)−0.0040 (8)0.0003 (9)−0.0048 (8)
C30.0131 (12)0.0138 (10)0.0118 (10)−0.0033 (9)0.0002 (8)−0.0065 (8)
C40.0166 (12)0.0126 (10)0.0109 (10)−0.0040 (9)0.0014 (8)−0.0018 (8)
C50.0161 (12)0.0087 (10)0.0146 (10)−0.0035 (8)−0.0004 (8)−0.0044 (8)
C60.0117 (11)0.0104 (10)0.0137 (10)−0.0022 (8)−0.0005 (8)−0.0051 (8)
C70.0132 (12)0.0102 (10)0.0143 (10)−0.0039 (8)−0.0018 (8)−0.0044 (8)
C80.0165 (12)0.0136 (10)0.0121 (10)−0.0044 (9)0.0006 (8)−0.0056 (8)
C90.0150 (12)0.0112 (10)0.0104 (9)−0.0009 (8)0.0011 (8)−0.0040 (8)
C100.0169 (12)0.0077 (10)0.0150 (10)−0.0043 (9)0.0004 (8)−0.0042 (8)
C110.0161 (12)0.0107 (10)0.0109 (10)−0.0014 (8)−0.0020 (8)−0.0064 (8)
C120.0165 (12)0.0125 (10)0.0124 (10)−0.0039 (9)0.0015 (8)−0.0041 (8)
C130.0132 (12)0.0111 (10)0.0156 (10)−0.0022 (8)−0.0016 (8)−0.0040 (8)
C140.0135 (12)0.0105 (10)0.0129 (10)−0.0018 (8)−0.0020 (8)−0.0056 (8)
C150.0138 (12)0.0108 (10)0.0144 (10)−0.0021 (8)−0.0016 (8)−0.0059 (8)
C160.0143 (12)0.0113 (10)0.0128 (10)−0.0006 (9)−0.0007 (8)−0.0046 (8)
C170.0160 (12)0.0123 (10)0.0116 (10)−0.0041 (9)0.0001 (8)−0.0031 (8)
C180.0163 (12)0.0120 (10)0.0148 (10)−0.0057 (9)0.0017 (9)−0.0067 (8)
C190.0118 (12)0.0181 (11)0.0134 (10)−0.0050 (9)0.0033 (8)−0.0085 (9)
C200.0179 (13)0.0149 (11)0.0112 (10)−0.0045 (9)0.0011 (9)−0.0025 (8)
C210.0202 (13)0.0102 (10)0.0161 (11)−0.0048 (9)0.0007 (9)−0.0044 (8)
C220.0148 (12)0.0125 (10)0.0145 (10)−0.0045 (9)0.0005 (8)−0.0063 (8)
C230.0171 (12)0.0123 (10)0.0165 (11)−0.0046 (9)−0.0007 (9)−0.0066 (9)
C240.0174 (12)0.0155 (11)0.0136 (10)−0.0068 (9)0.0002 (9)−0.0052 (9)

Geometric parameters (Å, °)

S1—C81.704 (2)N7—N81.388 (2)
S2—C161.698 (2)N8—C241.348 (3)
S3—C241.702 (2)N8—H810.858 (10)
O1—C11.360 (2)N9—C241.316 (3)
O1—H10.836 (10)N9—H910.857 (10)
O2—C21.383 (2)N9—H920.861 (10)
O2—H20.834 (10)C1—C21.383 (3)
O3—C31.360 (2)C1—C61.411 (3)
O3—H30.833 (10)C2—C31.394 (3)
O4—C91.362 (2)C3—C41.392 (3)
O4—H40.835 (10)C4—C51.381 (3)
O5—C101.374 (2)C4—H4A0.9500
O5—H50.831 (10)C5—C61.399 (3)
O6—C111.373 (2)C5—H5A0.9500
O6—H60.835 (10)C6—C71.445 (3)
O7—C171.360 (2)C7—H7A0.9500
O7—H70.830 (10)C9—C101.394 (3)
O8—C181.369 (2)C9—C141.406 (3)
O8—H80.837 (10)C10—C111.389 (3)
O9—C191.367 (2)C11—C121.385 (3)
O9—H90.840 (10)C12—C131.386 (3)
N1—C71.288 (3)C12—H120.9500
N1—N21.385 (2)C13—C141.398 (3)
N2—C81.344 (3)C13—H130.9500
N2—H210.860 (10)C14—C151.447 (3)
N3—C81.320 (3)C15—H150.9500
N3—H310.851 (10)C17—C181.398 (3)
N3—H320.853 (10)C17—C221.402 (3)
N4—C151.285 (3)C18—C191.390 (3)
N4—N51.385 (2)C19—C201.394 (3)
N5—C161.349 (3)C20—C211.380 (3)
N5—H510.865 (10)C20—H200.9500
N6—C161.323 (3)C21—C221.399 (3)
N6—H610.858 (10)C21—H21a0.9500
N6—H620.849 (10)C22—C231.454 (3)
N7—C231.288 (3)C23—H230.9500
C1—O1—H1108.4 (19)N3—C8—N2118.19 (19)
C2—O2—H2110 (2)N3—C8—S1123.33 (16)
C3—O3—H3108.4 (19)N2—C8—S1118.47 (16)
C9—O4—H4112 (2)O4—C9—C10117.13 (19)
C10—O5—H5104 (2)O4—C9—C14122.83 (19)
C11—O6—H6107.5 (19)C10—C9—C14120.01 (19)
C17—O7—H7106 (2)O5—C10—C11122.75 (19)
C18—O8—H8109 (2)O5—C10—C9117.48 (19)
C19—O9—H9108.1 (18)C11—C10—C9119.76 (19)
C7—N1—N2114.97 (17)O6—C11—C12123.38 (19)
C8—N2—N1120.71 (17)O6—C11—C10115.75 (19)
C8—N2—H21119.4 (17)C12—C11—C10120.87 (19)
N1—N2—H21119.2 (17)C13—C12—C11119.3 (2)
C8—N3—H31119.2 (19)C13—C12—H12120.3
C8—N3—H32121.1 (16)C11—C12—H12120.3
H31—N3—H32119 (2)C12—C13—C14121.2 (2)
C15—N4—N5116.06 (18)C12—C13—H13119.4
C16—N5—N4119.95 (18)C14—C13—H13119.4
C16—N5—H51122.7 (19)C13—C14—C9118.70 (19)
N4—N5—H51116.4 (19)C13—C14—C15119.20 (19)
C16—N6—H61121.8 (17)C9—C14—C15122.01 (19)
C16—N6—H62119.6 (17)N4—C15—C14122.3 (2)
H61—N6—H62118 (2)N4—C15—H15118.9
C23—N7—N8114.78 (18)C14—C15—H15118.9
C24—N8—N7120.06 (18)N6—C16—N5117.59 (19)
C24—N8—H81118.3 (16)N6—C16—S2123.38 (16)
N7—N8—H81121.4 (16)N5—C16—S2119.03 (16)
C24—N9—H91120.2 (17)O7—C17—C18117.13 (19)
C24—N9—H92118.8 (18)O7—C17—C22123.12 (19)
H91—N9—H92121 (2)C18—C17—C22119.74 (19)
O1—C1—C2118.45 (19)O8—C18—C19122.09 (19)
O1—C1—C6121.89 (18)O8—C18—C17117.80 (18)
C2—C1—C6119.65 (19)C19—C18—C17120.11 (19)
O2—C2—C1119.04 (18)O9—C19—C18115.08 (19)
O2—C2—C3120.19 (18)O9—C19—C20124.29 (19)
C1—C2—C3120.69 (19)C18—C19—C20120.6 (2)
O3—C3—C4123.43 (18)C21—C20—C19118.9 (2)
O3—C3—C2116.36 (18)C21—C20—H20120.5
C4—C3—C2120.20 (19)C19—C20—H20120.5
C5—C4—C3119.01 (19)C20—C21—C22121.8 (2)
C5—C4—H4A120.5C20—C21—H21a119.1
C3—C4—H4A120.5C22—C21—H21a119.1
C4—C5—C6121.78 (19)C21—C22—C17118.79 (19)
C4—C5—H5A119.1C21—C22—C23118.05 (19)
C6—C5—H5A119.1C17—C22—C23123.11 (19)
C5—C6—C1118.54 (19)N7—C23—C22122.12 (19)
C5—C6—C7118.53 (19)N7—C23—H23118.9
C1—C6—C7122.85 (19)C22—C23—H23118.9
N1—C7—C6122.49 (19)N9—C24—N8118.0 (2)
N1—C7—H7A118.8N9—C24—S3123.12 (17)
C6—C7—H7A118.8N8—C24—S3118.90 (16)
C7—N1—N2—C8−173.3 (2)C11—C12—C13—C141.5 (3)
C15—N4—N5—C16179.99 (19)C12—C13—C14—C91.6 (3)
C23—N7—N8—C24174.1 (2)C12—C13—C14—C15−175.1 (2)
O1—C1—C2—O23.8 (3)O4—C9—C14—C13177.55 (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—C30.8 (3)C10—C9—C14—C15172.0 (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—N4179.4 (2)
O2—C2—C3—C4179.20 (19)C9—C14—C15—N42.9 (3)
C1—C2—C3—C42.4 (3)N4—N5—C16—N61.8 (3)
O3—C3—C4—C5176.8 (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—C60.7 (3)C22—C17—C18—O8178.62 (19)
C4—C5—C6—C12.4 (3)O7—C17—C18—C19178.8 (2)
C4—C5—C6—C7−174.4 (2)C22—C17—C18—C19−0.8 (3)
O1—C1—C6—C5177.06 (19)O8—C18—C19—O9−0.4 (3)
C2—C1—C6—C5−3.1 (3)C17—C18—C19—O9178.91 (19)
O1—C1—C6—C7−6.3 (3)O8—C18—C19—C20179.7 (2)
C2—C1—C6—C7173.6 (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—N1176.6 (2)C18—C19—C20—C211.5 (3)
C1—C6—C7—N1−0.1 (3)C19—C20—C21—C22−0.3 (3)
N1—N2—C8—N31.5 (3)C20—C21—C22—C17−1.4 (3)
N1—N2—C8—S1−179.28 (15)C20—C21—C22—C23176.0 (2)
O4—C9—C10—O53.3 (3)O7—C17—C22—C21−177.6 (2)
C14—C9—C10—O5−174.69 (19)C18—C17—C22—C211.9 (3)
O4—C9—C10—C11−177.45 (18)O7—C17—C22—C235.2 (4)
C14—C9—C10—C114.5 (3)C18—C17—C22—C23−175.3 (2)
O5—C10—C11—O6−2.0 (3)N8—N7—C23—C22177.28 (19)
C9—C10—C11—O6178.77 (19)C21—C22—C23—N7−177.5 (2)
O5—C10—C11—C12177.7 (2)C17—C22—C23—N7−0.3 (4)
C9—C10—C11—C12−1.5 (3)N7—N8—C24—N90.3 (3)
O6—C11—C12—C13178.2 (2)N7—N8—C24—S3−179.20 (16)
C10—C11—C12—C13−1.6 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.84 (1)1.94 (2)2.682 (2)147 (3)
O2—H2···O3i0.83 (1)2.17 (2)2.773 (2)129 (3)
O3—H3···S1ii0.83 (1)2.36 (1)3.184 (2)173 (3)
O4—H4···N40.84 (1)1.96 (2)2.666 (2)141 (3)
O5—H5···O60.83 (1)2.24 (3)2.730 (2)118 (3)
O6—H6···S2ii0.84 (1)2.45 (1)3.276 (2)172 (2)
O7—H7···N70.83 (1)1.97 (2)2.710 (2)148 (3)
O8—H8···O90.84 (1)2.24 (3)2.697 (2)114 (2)
O9—H9···S3iii0.84 (1)2.40 (1)3.237 (2)174 (2)
N3—H31···O2iv0.85 (1)2.09 (1)2.902 (2)159 (3)
N6—H61···O8v0.86 (1)2.01 (1)2.847 (2)164 (2)
N9—H91···O5vi0.86 (1)2.11 (2)2.896 (2)153 (2)

Symmetry codes: (i) −x, −y+1, −z; (ii) x, y, z−1; (iii) x, y, z+1; (iv) −x, −y+1, −z+1; (v) x, y−1, z; (vi) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2242).

References

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  • Swesi, A. T., Farina, Y., Kassim, M. & Ng, S. W. (2006). Acta Cryst. E62, o5457–o5458.
  • Tan, K. W., Farina, Y., Ng, C. H., Maah, M. J. & Ng, S. W. (2008). Acta Cryst. E64, o1073. [PMC free article] [PubMed]
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