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ISSN: 2056-9890

3,4,5-Trihydr­­oxy-N′-(1H-indol-3-yl­methyl­­idene)benzohydrazide penta­hydrate

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 22 November 2008; accepted 22 November 2008; online 29 November 2008)

The two aromatic parts of the title compound, C16H13N3O4·5H2O, are connected through a conjugated –CH=N–NH–C(O)– fragment, giving an almost planar mol­ecule. The organic mol­ecules and uncoordinated water mol­ecules are linked by N—H⋯O and O—H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For the structure of anhydrous N′-(1H-indol-3-ylmethyl­idene)-3,4,5-trihydroxy­benzohydrazide, see: Khaledi et al. (2008[Khaledi, H., Mohd Ali, H. & Ng, S. W. (2008). Acta Cryst. E64, o2108.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13N3O4·5H2O

  • Mr = 401.37

  • Triclinic, [P \overline 1]

  • a = 7.4379 (2) Å

  • b = 9.1178 (2) Å

  • c = 14.1966 (3) Å

  • α = 103.814 (1)°

  • β = 103.716 (1)°

  • γ = 90.613 (2)°

  • V = 905.95 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.12 mm−1

  • T = 100 (2) K

  • 0.30 × 0.25 × 0.04 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: none

  • 7524 measured reflections

  • 4096 independent reflections

  • 3285 reflections with I > 2σ(I)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.115

  • S = 1.05

  • 4096 reflections

  • 313 parameters

  • 15 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.25 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1o⋯O4i 0.85 (1) 1.90 (1) 2.740 (2) 174 (2)
O2—H2o⋯O2w 0.84 (1) 1.94 (1) 2.697 (2) 149 (2)
O3—H3o⋯O3w 0.85 (1) 1.90 (1) 2.724 (2) 164 (2)
N1—H1n⋯O1wii 0.88 (1) 2.11 (1) 2.978 (2) 169 (2)
N3—H3n⋯O4wiii 0.88 (1) 2.15 (1) 3.024 (2) 171 (2)
O1w—H11⋯O1 0.85 (1) 1.93 (1) 2.771 (2) 170 (3)
O1w—H12⋯O3wiv 0.86 (1) 1.94 (1) 2.760 (2) 161 (3)
O2w—H21⋯O3v 0.84 (1) 2.29 (1) 3.123 (2) 172 (2)
O2w—H22⋯O5w 0.85 (1) 1.94 (2) 2.753 (2) 161 (3)
O3w—H31⋯O5wvi 0.85 (1) 1.95 (1) 2.796 (2) 172 (3)
O3w—H32⋯O3vii 0.85 (1) 2.06 (1) 2.890 (2) 165 (2)
O4w—H41⋯O1w 0.85 (1) 1.97 (1) 2.803 (2) 169 (2)
O4w—H42⋯O4viii 0.84 (1) 2.37 (2) 2.921 (2) 124 (2)
O4w—H42⋯N2viii 0.84 (1) 2.39 (1) 3.211 (2) 166 (2)
O5w—H51⋯O4wix 0.85 (1) 1.97 (1) 2.798 (2) 167 (2)
O5w—H52⋯O2wx 0.85 (1) 1.97 (1) 2.810 (2) 168 (3)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y+1, z; (iii) -x, -y+2, -z+1; (iv) x, y-1, z; (v) -x+1, -y+1, -z+2; (vi) x-1, y+1, z; (vii) -x+1, -y+2, -z+2; (viii) -x, -y+1, -z+1; (ix) x+1, y, z; (x) -x+2, -y+1, -z+2.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: pubCIF (Westrip, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


Related literature top

For the structure of anhydrous N'-(1H-indol-3-ylmethylidene)-3,4,5-trihydroxybenzohydrazide, see: Khaledi et al. (2008).

Experimental top

Indole-3-carbaldehyde (1.0 g, 7 mmol) and 3,4,5-trihydroxybenzoylhydrazine (1.29 g, 7 mmol) were heated in ethanol (60 ml) for 6 h. About 1 ml of acetic acid also added. The solution was set aside for the growth of crystals.

Refinement top

Hydrogen atoms were placed at calculated positions (C–H 0.95 Å), and were treated as riding on their parent carbon atoms, with U(H) set to 1.2Ueq(C). The nitrogen- and oxygen-bound H atoms were located in a difference Fourier map, and were refined with distance restraints of N–H 0.88±0.01 and O–H 0.84±0.01 Å.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: pubCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C16H13N3O4.5H2O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
3,4,5-Trihydroxy-N'-(1H-indol-3-ylmethylidene)benzohydrazide pentahydrate top
Crystal data top
C16H13N3O4·5H2OZ = 2
Mr = 401.37F(000) = 424
Triclinic, P1Dx = 1.471 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4379 (2) ÅCell parameters from 2461 reflections
b = 9.1178 (2) Åθ = 2.3–28.0°
c = 14.1966 (3) ŵ = 0.12 mm1
α = 103.814 (1)°T = 100 K
β = 103.716 (1)°Plate, pale-yellow
γ = 90.613 (2)°0.30 × 0.25 × 0.04 mm
V = 905.95 (4) Å3
Data collection top
Bruker SMART APEX
diffractometer
3285 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 27.5°, θmin = 2.3°
ω scansh = 99
7524 measured reflectionsk = 1111
4096 independent reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0613P)2 + 0.1789P]
where P = (Fo2 + 2Fc2)/3
4096 reflections(Δ/σ)max = 0.001
313 parametersΔρmax = 0.35 e Å3
15 restraintsΔρmin = 0.25 e Å3
Crystal data top
C16H13N3O4·5H2Oγ = 90.613 (2)°
Mr = 401.37V = 905.95 (4) Å3
Triclinic, P1Z = 2
a = 7.4379 (2) ÅMo Kα radiation
b = 9.1178 (2) ŵ = 0.12 mm1
c = 14.1966 (3) ÅT = 100 K
α = 103.814 (1)°0.30 × 0.25 × 0.04 mm
β = 103.716 (1)°
Data collection top
Bruker SMART APEX
diffractometer
3285 reflections with I > 2σ(I)
7524 measured reflectionsRint = 0.023
4096 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04115 restraints
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.35 e Å3
4096 reflectionsΔρmin = 0.25 e Å3
313 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.59471 (16)0.40029 (12)0.72041 (8)0.0184 (2)
O20.51512 (17)0.56940 (13)0.89648 (8)0.0217 (3)
O30.35915 (16)0.82334 (12)0.90287 (8)0.0180 (2)
O40.31349 (16)0.68239 (12)0.45992 (8)0.0197 (3)
O1w0.35758 (17)0.17412 (13)0.73409 (8)0.0200 (3)
O2w0.75855 (17)0.38643 (13)0.97416 (9)0.0221 (3)
O3w0.34432 (17)1.12598 (13)0.91713 (8)0.0213 (3)
O4w0.01511 (18)0.30256 (13)0.69710 (9)0.0231 (3)
O5w1.07168 (17)0.33392 (13)0.90316 (9)0.0232 (3)
N10.29295 (19)0.91884 (14)0.55157 (9)0.0162 (3)
N20.24067 (18)0.97264 (14)0.46592 (9)0.0165 (3)
N30.08352 (19)1.39294 (15)0.34212 (10)0.0183 (3)
C10.4530 (2)0.58425 (16)0.63391 (11)0.0147 (3)
H10.47530.52740.57290.018*
C20.5040 (2)0.53102 (16)0.71918 (11)0.0146 (3)
C30.4698 (2)0.61229 (17)0.80875 (11)0.0151 (3)
C40.3855 (2)0.74827 (16)0.81103 (11)0.0147 (3)
C50.3332 (2)0.80233 (16)0.72644 (11)0.0148 (3)
H50.27330.89420.72900.018*
C60.3693 (2)0.72070 (16)0.63685 (10)0.0140 (3)
C70.3236 (2)0.77172 (16)0.54225 (11)0.0144 (3)
C80.2179 (2)1.11562 (17)0.48486 (11)0.0168 (3)
H80.23541.17000.55280.020*
C90.1240 (2)1.34618 (17)0.42795 (11)0.0175 (3)
H90.12261.40730.49210.021*
C100.1675 (2)1.19684 (17)0.40875 (11)0.0158 (3)
C110.1553 (2)1.14989 (17)0.30295 (11)0.0154 (3)
C120.1934 (2)1.01736 (17)0.23897 (11)0.0194 (3)
H12A0.22990.93100.26320.023*
C130.1763 (2)1.01605 (19)0.13982 (12)0.0229 (4)
H130.20230.92750.09560.028*
C140.1213 (2)1.1422 (2)0.10270 (12)0.0241 (4)
H140.10931.13670.03380.029*
C150.0845 (2)1.27369 (19)0.16400 (12)0.0212 (3)
H150.04781.35940.13900.025*
C160.1033 (2)1.27600 (17)0.26438 (11)0.0169 (3)
H1o0.616 (3)0.370 (2)0.6634 (10)0.046 (7)*
H2o0.584 (3)0.4971 (18)0.8974 (16)0.039 (6)*
H3o0.333 (3)0.9129 (14)0.8998 (16)0.038 (6)*
H1n0.314 (3)0.9850 (17)0.6102 (9)0.025 (5)*
H3n0.052 (3)1.4844 (15)0.3374 (17)0.046 (6)*
H110.438 (3)0.235 (2)0.7274 (19)0.060 (8)*
H120.380 (4)0.163 (3)0.7939 (10)0.059 (8)*
H210.719 (3)0.336 (2)1.0090 (16)0.055 (7)*
H220.848 (3)0.349 (4)0.952 (2)0.112 (13)*
H310.255 (3)1.184 (3)0.915 (2)0.067 (9)*
H320.425 (2)1.158 (2)0.9721 (10)0.037 (6)*
H410.117 (2)0.260 (3)0.7001 (18)0.055 (8)*
H420.066 (3)0.242 (2)0.6537 (15)0.063 (8)*
H511.039 (3)0.331 (3)0.8414 (8)0.055 (8)*
H521.124 (4)0.4219 (19)0.932 (2)0.101 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0248 (6)0.0168 (5)0.0172 (6)0.0079 (5)0.0091 (5)0.0068 (4)
O20.0281 (7)0.0247 (6)0.0164 (6)0.0119 (5)0.0081 (5)0.0099 (5)
O30.0241 (6)0.0179 (6)0.0123 (5)0.0060 (5)0.0060 (4)0.0026 (4)
O40.0282 (6)0.0169 (5)0.0131 (5)0.0037 (5)0.0051 (5)0.0021 (4)
O1w0.0247 (6)0.0202 (6)0.0156 (6)0.0008 (5)0.0053 (5)0.0051 (4)
O2w0.0242 (7)0.0240 (6)0.0223 (6)0.0054 (5)0.0101 (5)0.0094 (5)
O3w0.0235 (6)0.0233 (6)0.0155 (6)0.0042 (5)0.0031 (5)0.0032 (4)
O4w0.0217 (6)0.0249 (6)0.0217 (6)0.0056 (5)0.0035 (5)0.0057 (5)
O5w0.0249 (7)0.0234 (6)0.0203 (6)0.0028 (5)0.0070 (5)0.0023 (5)
N10.0228 (7)0.0147 (6)0.0106 (6)0.0027 (5)0.0029 (5)0.0037 (5)
N20.0201 (7)0.0179 (6)0.0127 (6)0.0027 (5)0.0041 (5)0.0063 (5)
N30.0196 (7)0.0150 (6)0.0212 (7)0.0033 (5)0.0041 (5)0.0069 (5)
C10.0158 (7)0.0148 (7)0.0129 (7)0.0006 (6)0.0040 (6)0.0019 (5)
C20.0143 (7)0.0127 (7)0.0176 (7)0.0014 (6)0.0046 (6)0.0043 (6)
C30.0144 (7)0.0181 (7)0.0138 (7)0.0005 (6)0.0034 (6)0.0060 (6)
C40.0140 (7)0.0166 (7)0.0126 (7)0.0003 (6)0.0046 (6)0.0009 (5)
C50.0158 (7)0.0131 (7)0.0152 (7)0.0019 (6)0.0040 (6)0.0028 (5)
C60.0136 (7)0.0148 (7)0.0125 (7)0.0014 (6)0.0019 (5)0.0030 (5)
C70.0142 (7)0.0159 (7)0.0132 (7)0.0002 (6)0.0033 (6)0.0037 (5)
C80.0191 (8)0.0175 (7)0.0136 (7)0.0022 (6)0.0041 (6)0.0032 (6)
C90.0177 (8)0.0176 (7)0.0169 (7)0.0013 (6)0.0038 (6)0.0043 (6)
C100.0164 (7)0.0154 (7)0.0155 (7)0.0012 (6)0.0035 (6)0.0042 (6)
C110.0153 (7)0.0175 (7)0.0134 (7)0.0011 (6)0.0027 (6)0.0046 (6)
C120.0202 (8)0.0174 (7)0.0194 (8)0.0010 (6)0.0042 (6)0.0031 (6)
C130.0249 (9)0.0226 (8)0.0191 (8)0.0037 (7)0.0070 (7)0.0005 (6)
C140.0242 (9)0.0322 (9)0.0145 (7)0.0084 (7)0.0028 (6)0.0054 (6)
C150.0185 (8)0.0264 (8)0.0191 (8)0.0041 (7)0.0002 (6)0.0109 (6)
C160.0137 (7)0.0184 (7)0.0178 (7)0.0017 (6)0.0016 (6)0.0054 (6)
Geometric parameters (Å, º) top
O1—C21.3777 (18)C1—C21.383 (2)
O1—H1o0.845 (9)C1—C61.393 (2)
O2—C31.3615 (18)C1—H10.9500
O2—H2o0.839 (10)C2—C31.392 (2)
O3—C41.3801 (17)C3—C41.392 (2)
O3—H3o0.851 (10)C4—C51.379 (2)
O4—C71.2400 (17)C5—C61.399 (2)
O1w—H110.850 (10)C5—H50.9500
O1w—H120.855 (10)C6—C71.490 (2)
O2w—H210.843 (10)C8—C101.433 (2)
O2w—H220.846 (10)C8—H80.9500
O3w—H310.854 (10)C9—C101.381 (2)
O3w—H320.848 (10)C9—H90.9500
O4w—H410.848 (10)C10—C111.441 (2)
O4w—H420.839 (10)C11—C121.404 (2)
O5w—H510.847 (10)C11—C161.408 (2)
O5w—H520.850 (10)C12—C131.380 (2)
N1—C71.3434 (19)C12—H12A0.9500
N1—N21.3910 (17)C13—C141.402 (2)
N1—H1n0.882 (9)C13—H130.9500
N2—C81.288 (2)C14—C151.375 (2)
N3—C91.354 (2)C14—H140.9500
N3—C161.376 (2)C15—C161.394 (2)
N3—H3n0.882 (10)C15—H150.9500
C2—O1—H1o106.5 (16)C5—C6—C7123.54 (13)
C3—O2—H2o115.8 (15)O4—C7—N1122.36 (13)
C4—O3—H3o107.5 (14)O4—C7—C6121.46 (13)
H11—O1w—H12112 (2)N1—C7—C6116.18 (13)
H21—O2w—H22114 (3)N2—C8—C10123.34 (14)
H31—O3w—H32109 (2)N2—C8—H8118.3
H41—O4w—H42107 (2)C10—C8—H8118.3
H51—O5w—H52106 (3)N3—C9—C10110.20 (14)
C7—N1—N2119.24 (12)N3—C9—H9124.9
C7—N1—H1n122.5 (12)C10—C9—H9124.9
N2—N1—H1n118.0 (12)C9—C10—C8123.34 (14)
C8—N2—N1113.26 (12)C9—C10—C11106.25 (13)
C9—N3—C16109.03 (13)C8—C10—C11130.40 (14)
C9—N3—H3n125.2 (15)C12—C11—C16119.25 (14)
C16—N3—H3n125.7 (15)C12—C11—C10134.26 (14)
C2—C1—C6120.49 (13)C16—C11—C10106.36 (13)
C2—C1—H1119.8C13—C12—C11118.14 (15)
C6—C1—H1119.8C13—C12—H12A120.9
O1—C2—C1122.20 (13)C11—C12—H12A120.9
O1—C2—C3117.48 (13)C12—C13—C14121.62 (15)
C1—C2—C3120.29 (14)C12—C13—H13119.2
O2—C3—C4116.52 (13)C14—C13—H13119.2
O2—C3—C2124.59 (14)C15—C14—C13121.35 (15)
C4—C3—C2118.89 (13)C15—C14—H14119.3
O3—C4—C5123.17 (14)C13—C14—H14119.3
O3—C4—C3115.42 (13)C14—C15—C16117.23 (15)
C5—C4—C3121.41 (13)C14—C15—H15121.4
C4—C5—C6119.40 (14)C16—C15—H15121.4
C4—C5—H5120.3N3—C16—C15129.42 (14)
C6—C5—H5120.3N3—C16—C11108.14 (13)
C1—C6—C5119.50 (13)C15—C16—C11122.40 (15)
C1—C6—C7116.96 (13)
C7—N1—N2—C8179.15 (14)N1—N2—C8—C10178.78 (14)
C6—C1—C2—O1176.94 (13)C16—N3—C9—C101.24 (18)
C6—C1—C2—C30.9 (2)N3—C9—C10—C8179.52 (14)
O1—C2—C3—O21.9 (2)N3—C9—C10—C110.96 (18)
C1—C2—C3—O2179.82 (14)N2—C8—C10—C9172.92 (15)
O1—C2—C3—C4177.27 (13)N2—C8—C10—C118.9 (3)
C1—C2—C3—C40.7 (2)C9—C10—C11—C12175.33 (17)
O2—C3—C4—O30.3 (2)C8—C10—C11—C123.1 (3)
C2—C3—C4—O3178.94 (13)C9—C10—C11—C160.34 (17)
O2—C3—C4—C5179.82 (13)C8—C10—C11—C16178.76 (16)
C2—C3—C4—C51.0 (2)C16—C11—C12—C130.6 (2)
O3—C4—C5—C6178.43 (13)C10—C11—C12—C13175.81 (16)
C3—C4—C5—C61.5 (2)C11—C12—C13—C140.4 (2)
C2—C1—C6—C51.4 (2)C12—C13—C14—C150.9 (3)
C2—C1—C6—C7178.38 (13)C13—C14—C15—C160.3 (2)
C4—C5—C6—C11.7 (2)C9—N3—C16—C15176.86 (16)
C4—C5—C6—C7178.10 (13)C9—N3—C16—C110.99 (17)
N2—N1—C7—O42.7 (2)C14—C15—C16—N3176.83 (16)
N2—N1—C7—C6176.87 (12)C14—C15—C16—C110.8 (2)
C1—C6—C7—O418.6 (2)C12—C11—C16—N3176.83 (14)
C5—C6—C7—O4161.64 (14)C10—C11—C16—N30.38 (17)
C1—C6—C7—N1161.86 (13)C12—C11—C16—C151.2 (2)
C5—C6—C7—N117.9 (2)C10—C11—C16—C15177.65 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···O4i0.85 (1)1.90 (1)2.740 (2)174 (2)
O2—H2o···O2w0.84 (1)1.94 (1)2.697 (2)149 (2)
O3—H3o···O3w0.85 (1)1.90 (1)2.724 (2)164 (2)
N1—H1n···O1wii0.88 (1)2.11 (1)2.978 (2)169 (2)
N3—H3n···O4wiii0.88 (1)2.15 (1)3.024 (2)171 (2)
O1w—H11···O10.85 (1)1.93 (1)2.771 (2)170 (3)
O1w—H12···O3wiv0.86 (1)1.94 (1)2.760 (2)161 (3)
O2w—H21···O3v0.84 (1)2.29 (1)3.123 (2)172 (2)
O2w—H22···O5w0.85 (1)1.94 (2)2.753 (2)161 (3)
O3w—H31···O5wvi0.85 (1)1.95 (1)2.796 (2)172 (3)
O3w—H32···O3vii0.85 (1)2.06 (1)2.890 (2)165 (2)
O4w—H41···O1w0.85 (1)1.97 (1)2.803 (2)169 (2)
O4w—H42···O4viii0.84 (1)2.37 (2)2.921 (2)124 (2)
O4w—H42···N2viii0.84 (1)2.39 (1)3.211 (2)166 (2)
O5w—H51···O4wix0.85 (1)1.97 (1)2.798 (2)167 (2)
O5w—H52···O2wx0.85 (1)1.97 (1)2.810 (2)168 (3)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z; (iii) x, y+2, z+1; (iv) x, y1, z; (v) x+1, y+1, z+2; (vi) x1, y+1, z; (vii) x+1, y+2, z+2; (viii) x, y+1, z+1; (ix) x+1, y, z; (x) x+2, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC16H13N3O4·5H2O
Mr401.37
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.4379 (2), 9.1178 (2), 14.1966 (3)
α, β, γ (°)103.814 (1), 103.716 (1), 90.613 (2)
V3)905.95 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.30 × 0.25 × 0.04
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
7524, 4096, 3285
Rint0.023
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.115, 1.05
No. of reflections4096
No. of parameters313
No. of restraints15
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.35, 0.25

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), pubCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···O4i0.85 (1)1.90 (1)2.740 (2)174 (2)
O2—H2o···O2w0.84 (1)1.94 (1)2.697 (2)149 (2)
O3—H3o···O3w0.85 (1)1.90 (1)2.724 (2)164 (2)
N1—H1n···O1wii0.88 (1)2.11 (1)2.978 (2)169 (2)
N3—H3n···O4wiii0.88 (1)2.15 (1)3.024 (2)171 (2)
O1w—H11···O10.85 (1)1.93 (1)2.771 (2)170 (3)
O1w—H12···O3wiv0.86 (1)1.94 (1)2.760 (2)161 (3)
O2w—H21···O3v0.84 (1)2.29 (1)3.123 (2)172 (2)
O2w—H22···O5w0.85 (1)1.94 (2)2.753 (2)161 (3)
O3w—H31···O5wvi0.85 (1)1.95 (1)2.796 (2)172 (3)
O3w—H32···O3vii0.85 (1)2.06 (1)2.890 (2)165 (2)
O4w—H41···O1w0.85 (1)1.97 (1)2.803 (2)169 (2)
O4w—H42···O4viii0.84 (1)2.37 (2)2.921 (2)124 (2)
O4w—H42···N2viii0.84 (1)2.39 (1)3.211 (2)166 (2)
O5w—H51···O4wix0.85 (1)1.97 (1)2.798 (2)167 (2)
O5w—H52···O2wx0.85 (1)1.97 (1)2.810 (2)168 (3)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z; (iii) x, y+2, z+1; (iv) x, y1, z; (v) x+1, y+1, z+2; (vi) x1, y+1, z; (vii) x+1, y+2, z+2; (viii) x, y+1, z+1; (ix) x+1, y, z; (x) x+2, y+1, z+2.
 

Acknowledgements

We thank the University of Malaya for funding this study (Science Fund grants 12–02-03–2031 and 12–02-03–2051).

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationKhaledi, H., Mohd Ali, H. & Ng, S. W. (2008). Acta Cryst. E64, o2108.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2008). publCIF. In preparation.  Google Scholar

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