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

Khaledi, H.; Mohd Ali, H.; Ng, S.W.

doi:10.1107/S1600536808039342

organic compounds

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Volume 64| Part 12| December 2008| Page o2481

doi:10.1107/S1600536808039342

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

Hamid Khaledi,^a Hapipah Mohd Ali ^a and Seik Weng Ng ^a ^*

^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 ).

Experimental

Crystal data

C₁₆H₁₃N₃O₄·5H₂O
M_r = 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)
R_int = 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
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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⋯O3w^iv	0.86 (1)	1.94 (1)	2.760 (2)	161 (3)
O2w—H21⋯O3^v	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⋯O5w^vi	0.85 (1)	1.95 (1)	2.796 (2)	172 (3)
O3w—H32⋯O3^vii	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⋯O4^viii	0.84 (1)	2.37 (2)	2.921 (2)	124 (2)
O4w—H42⋯N2^viii	0.84 (1)	2.39 (1)	3.211 (2)	166 (2)
O5w—H51⋯O4w^ix	0.85 (1)	1.97 (1)	2.798 (2)	167 (2)
O5w—H52⋯O2w^x	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 ); cell refinement: APEX2; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039342/tk2335sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808039342/tk2335Isup2.hkl

checkCIF report

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.

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

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

C₁₆H₁₃N₃O₄·5H₂O	Z = 2
M_r = 401.37	F(000) = 424
Triclinic, P1	D_x = 1.471 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4379 (2) Å	Cell parameters from 2461 reflections
b = 9.1178 (2) Å	θ = 2.3–28.0°
c = 14.1966 (3) Å	µ = 0.12 mm⁻¹
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 tube	R_int = 0.023
Graphite monochromator	θ_max = 27.5°, θ_min = 2.3°
ω scans	h = −9→9
7524 measured reflections	k = −11→11
4096 independent reflections	l = −18→18

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0613P)² + 0.1789P] where P = (F_o² + 2F_c²)/3
4096 reflections	(Δ/σ)_max = 0.001
313 parameters	Δρ_max = 0.35 e Å⁻³
15 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₆H₁₃N₃O₄·5H₂O	γ = 90.613 (2)°
M_r = 401.37	V = 905.95 (4) Å³
Triclinic, P1	Z = 2
a = 7.4379 (2) Å	Mo Kα radiation
b = 9.1178 (2) Å	µ = 0.12 mm⁻¹
c = 14.1966 (3) Å	T = 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 reflections	R_int = 0.023
4096 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	15 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.35 e Å⁻³
4096 reflections	Δρ_min = −0.25 e Å⁻³
313 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.59471 (16)	0.40029 (12)	0.72041 (8)	0.0184 (2)
O2	0.51512 (17)	0.56940 (13)	0.89648 (8)	0.0217 (3)
O3	0.35915 (16)	0.82334 (12)	0.90287 (8)	0.0180 (2)
O4	0.31349 (16)	0.68239 (12)	0.45992 (8)	0.0197 (3)
O1w	0.35758 (17)	0.17412 (13)	0.73409 (8)	0.0200 (3)
O2w	0.75855 (17)	0.38643 (13)	0.97416 (9)	0.0221 (3)
O3w	0.34432 (17)	1.12598 (13)	0.91713 (8)	0.0213 (3)
O4w	0.01511 (18)	0.30256 (13)	0.69710 (9)	0.0231 (3)
O5w	1.07168 (17)	0.33392 (13)	0.90316 (9)	0.0232 (3)
N1	0.29295 (19)	0.91884 (14)	0.55157 (9)	0.0162 (3)
N2	0.24067 (18)	0.97264 (14)	0.46592 (9)	0.0165 (3)
N3	0.08352 (19)	1.39294 (15)	0.34212 (10)	0.0183 (3)
C1	0.4530 (2)	0.58425 (16)	0.63391 (11)	0.0147 (3)
H1	0.4753	0.5274	0.5729	0.018*
C2	0.5040 (2)	0.53102 (16)	0.71918 (11)	0.0146 (3)
C3	0.4698 (2)	0.61229 (17)	0.80875 (11)	0.0151 (3)
C4	0.3855 (2)	0.74827 (16)	0.81103 (11)	0.0147 (3)
C5	0.3332 (2)	0.80233 (16)	0.72644 (11)	0.0148 (3)
H5	0.2733	0.8942	0.7290	0.018*
C6	0.3693 (2)	0.72070 (16)	0.63685 (10)	0.0140 (3)
C7	0.3236 (2)	0.77172 (16)	0.54225 (11)	0.0144 (3)
C8	0.2179 (2)	1.11562 (17)	0.48486 (11)	0.0168 (3)
H8	0.2354	1.1700	0.5528	0.020*
C9	0.1240 (2)	1.34618 (17)	0.42795 (11)	0.0175 (3)
H9	0.1226	1.4073	0.4921	0.021*
C10	0.1675 (2)	1.19684 (17)	0.40875 (11)	0.0158 (3)
C11	0.1553 (2)	1.14989 (17)	0.30295 (11)	0.0154 (3)
C12	0.1934 (2)	1.01736 (17)	0.23897 (11)	0.0194 (3)
H12A	0.2299	0.9310	0.2632	0.023*
C13	0.1763 (2)	1.01605 (19)	0.13982 (12)	0.0229 (4)
H13	0.2023	0.9275	0.0956	0.028*
C14	0.1213 (2)	1.1422 (2)	0.10270 (12)	0.0241 (4)
H14	0.1093	1.1367	0.0338	0.029*
C15	0.0845 (2)	1.27369 (19)	0.16400 (12)	0.0212 (3)
H15	0.0478	1.3594	0.1390	0.025*
C16	0.1033 (2)	1.27600 (17)	0.26438 (11)	0.0169 (3)
H1o	0.616 (3)	0.370 (2)	0.6634 (10)	0.046 (7)*
H2o	0.584 (3)	0.4971 (18)	0.8974 (16)	0.039 (6)*
H3o	0.333 (3)	0.9129 (14)	0.8998 (16)	0.038 (6)*
H1n	0.314 (3)	0.9850 (17)	0.6102 (9)	0.025 (5)*
H3n	0.052 (3)	1.4844 (15)	0.3374 (17)	0.046 (6)*
H11	0.438 (3)	0.235 (2)	0.7274 (19)	0.060 (8)*
H12	0.380 (4)	0.163 (3)	0.7939 (10)	0.059 (8)*
H21	0.719 (3)	0.336 (2)	1.0090 (16)	0.055 (7)*
H22	0.848 (3)	0.349 (4)	0.952 (2)	0.112 (13)*
H31	0.255 (3)	1.184 (3)	0.915 (2)	0.067 (9)*
H32	0.425 (2)	1.158 (2)	0.9721 (10)	0.037 (6)*
H41	0.117 (2)	0.260 (3)	0.7001 (18)	0.055 (8)*
H42	−0.066 (3)	0.242 (2)	0.6537 (15)	0.063 (8)*
H51	1.039 (3)	0.331 (3)	0.8414 (8)	0.055 (8)*
H52	1.124 (4)	0.4219 (19)	0.932 (2)	0.101 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0248 (6)	0.0168 (5)	0.0172 (6)	0.0079 (5)	0.0091 (5)	0.0068 (4)
O2	0.0281 (7)	0.0247 (6)	0.0164 (6)	0.0119 (5)	0.0081 (5)	0.0099 (5)
O3	0.0241 (6)	0.0179 (6)	0.0123 (5)	0.0060 (5)	0.0060 (4)	0.0026 (4)
O4	0.0282 (6)	0.0169 (5)	0.0131 (5)	0.0037 (5)	0.0051 (5)	0.0021 (4)
O1w	0.0247 (6)	0.0202 (6)	0.0156 (6)	0.0008 (5)	0.0053 (5)	0.0051 (4)
O2w	0.0242 (7)	0.0240 (6)	0.0223 (6)	0.0054 (5)	0.0101 (5)	0.0094 (5)
O3w	0.0235 (6)	0.0233 (6)	0.0155 (6)	0.0042 (5)	0.0031 (5)	0.0032 (4)
O4w	0.0217 (6)	0.0249 (6)	0.0217 (6)	0.0056 (5)	0.0035 (5)	0.0057 (5)
O5w	0.0249 (7)	0.0234 (6)	0.0203 (6)	0.0028 (5)	0.0070 (5)	0.0023 (5)
N1	0.0228 (7)	0.0147 (6)	0.0106 (6)	0.0027 (5)	0.0029 (5)	0.0037 (5)
N2	0.0201 (7)	0.0179 (6)	0.0127 (6)	0.0027 (5)	0.0041 (5)	0.0063 (5)
N3	0.0196 (7)	0.0150 (6)	0.0212 (7)	0.0033 (5)	0.0041 (5)	0.0069 (5)
C1	0.0158 (7)	0.0148 (7)	0.0129 (7)	0.0006 (6)	0.0040 (6)	0.0019 (5)
C2	0.0143 (7)	0.0127 (7)	0.0176 (7)	0.0014 (6)	0.0046 (6)	0.0043 (6)
C3	0.0144 (7)	0.0181 (7)	0.0138 (7)	0.0005 (6)	0.0034 (6)	0.0060 (6)
C4	0.0140 (7)	0.0166 (7)	0.0126 (7)	−0.0003 (6)	0.0046 (6)	0.0009 (5)
C5	0.0158 (7)	0.0131 (7)	0.0152 (7)	0.0019 (6)	0.0040 (6)	0.0028 (5)
C6	0.0136 (7)	0.0148 (7)	0.0125 (7)	−0.0014 (6)	0.0019 (5)	0.0030 (5)
C7	0.0142 (7)	0.0159 (7)	0.0132 (7)	0.0002 (6)	0.0033 (6)	0.0037 (5)
C8	0.0191 (8)	0.0175 (7)	0.0136 (7)	0.0022 (6)	0.0041 (6)	0.0032 (6)
C9	0.0177 (8)	0.0176 (7)	0.0169 (7)	0.0013 (6)	0.0038 (6)	0.0043 (6)
C10	0.0164 (7)	0.0154 (7)	0.0155 (7)	0.0012 (6)	0.0035 (6)	0.0042 (6)
C11	0.0153 (7)	0.0175 (7)	0.0134 (7)	−0.0011 (6)	0.0027 (6)	0.0046 (6)
C12	0.0202 (8)	0.0174 (7)	0.0194 (8)	−0.0010 (6)	0.0042 (6)	0.0031 (6)
C13	0.0249 (9)	0.0226 (8)	0.0191 (8)	−0.0037 (7)	0.0070 (7)	−0.0005 (6)
C14	0.0242 (9)	0.0322 (9)	0.0145 (7)	−0.0084 (7)	0.0028 (6)	0.0054 (6)
C15	0.0185 (8)	0.0264 (8)	0.0191 (8)	−0.0041 (7)	0.0002 (6)	0.0109 (6)
C16	0.0137 (7)	0.0184 (7)	0.0178 (7)	−0.0017 (6)	0.0016 (6)	0.0054 (6)

Geometric parameters (Å, º) top

O1—C2	1.3777 (18)	C1—C2	1.383 (2)
O1—H1o	0.845 (9)	C1—C6	1.393 (2)
O2—C3	1.3615 (18)	C1—H1	0.9500
O2—H2o	0.839 (10)	C2—C3	1.392 (2)
O3—C4	1.3801 (17)	C3—C4	1.392 (2)
O3—H3o	0.851 (10)	C4—C5	1.379 (2)
O4—C7	1.2400 (17)	C5—C6	1.399 (2)
O1w—H11	0.850 (10)	C5—H5	0.9500
O1w—H12	0.855 (10)	C6—C7	1.490 (2)
O2w—H21	0.843 (10)	C8—C10	1.433 (2)
O2w—H22	0.846 (10)	C8—H8	0.9500
O3w—H31	0.854 (10)	C9—C10	1.381 (2)
O3w—H32	0.848 (10)	C9—H9	0.9500
O4w—H41	0.848 (10)	C10—C11	1.441 (2)
O4w—H42	0.839 (10)	C11—C12	1.404 (2)
O5w—H51	0.847 (10)	C11—C16	1.408 (2)
O5w—H52	0.850 (10)	C12—C13	1.380 (2)
N1—C7	1.3434 (19)	C12—H12A	0.9500
N1—N2	1.3910 (17)	C13—C14	1.402 (2)
N1—H1n	0.882 (9)	C13—H13	0.9500
N2—C8	1.288 (2)	C14—C15	1.375 (2)
N3—C9	1.354 (2)	C14—H14	0.9500
N3—C16	1.376 (2)	C15—C16	1.394 (2)
N3—H3n	0.882 (10)	C15—H15	0.9500

C2—O1—H1o	106.5 (16)	C5—C6—C7	123.54 (13)
C3—O2—H2o	115.8 (15)	O4—C7—N1	122.36 (13)
C4—O3—H3o	107.5 (14)	O4—C7—C6	121.46 (13)
H11—O1w—H12	112 (2)	N1—C7—C6	116.18 (13)
H21—O2w—H22	114 (3)	N2—C8—C10	123.34 (14)
H31—O3w—H32	109 (2)	N2—C8—H8	118.3
H41—O4w—H42	107 (2)	C10—C8—H8	118.3
H51—O5w—H52	106 (3)	N3—C9—C10	110.20 (14)
C7—N1—N2	119.24 (12)	N3—C9—H9	124.9
C7—N1—H1n	122.5 (12)	C10—C9—H9	124.9
N2—N1—H1n	118.0 (12)	C9—C10—C8	123.34 (14)
C8—N2—N1	113.26 (12)	C9—C10—C11	106.25 (13)
C9—N3—C16	109.03 (13)	C8—C10—C11	130.40 (14)
C9—N3—H3n	125.2 (15)	C12—C11—C16	119.25 (14)
C16—N3—H3n	125.7 (15)	C12—C11—C10	134.26 (14)
C2—C1—C6	120.49 (13)	C16—C11—C10	106.36 (13)
C2—C1—H1	119.8	C13—C12—C11	118.14 (15)
C6—C1—H1	119.8	C13—C12—H12A	120.9
O1—C2—C1	122.20 (13)	C11—C12—H12A	120.9
O1—C2—C3	117.48 (13)	C12—C13—C14	121.62 (15)
C1—C2—C3	120.29 (14)	C12—C13—H13	119.2
O2—C3—C4	116.52 (13)	C14—C13—H13	119.2
O2—C3—C2	124.59 (14)	C15—C14—C13	121.35 (15)
C4—C3—C2	118.89 (13)	C15—C14—H14	119.3
O3—C4—C5	123.17 (14)	C13—C14—H14	119.3
O3—C4—C3	115.42 (13)	C14—C15—C16	117.23 (15)
C5—C4—C3	121.41 (13)	C14—C15—H15	121.4
C4—C5—C6	119.40 (14)	C16—C15—H15	121.4
C4—C5—H5	120.3	N3—C16—C15	129.42 (14)
C6—C5—H5	120.3	N3—C16—C11	108.14 (13)
C1—C6—C5	119.50 (13)	C15—C16—C11	122.40 (15)
C1—C6—C7	116.96 (13)

C7—N1—N2—C8	−179.15 (14)	N1—N2—C8—C10	178.78 (14)
C6—C1—C2—O1	−176.94 (13)	C16—N3—C9—C10	−1.24 (18)
C6—C1—C2—C3	0.9 (2)	N3—C9—C10—C8	179.52 (14)
O1—C2—C3—O2	−1.9 (2)	N3—C9—C10—C11	0.96 (18)
C1—C2—C3—O2	−179.82 (14)	N2—C8—C10—C9	172.92 (15)
O1—C2—C3—C4	177.27 (13)	N2—C8—C10—C11	−8.9 (3)
C1—C2—C3—C4	−0.7 (2)	C9—C10—C11—C12	175.33 (17)
O2—C3—C4—O3	0.3 (2)	C8—C10—C11—C12	−3.1 (3)
C2—C3—C4—O3	−178.94 (13)	C9—C10—C11—C16	−0.34 (17)
O2—C3—C4—C5	−179.82 (13)	C8—C10—C11—C16	−178.76 (16)
C2—C3—C4—C5	1.0 (2)	C16—C11—C12—C13	−0.6 (2)
O3—C4—C5—C6	178.43 (13)	C10—C11—C12—C13	−175.81 (16)
C3—C4—C5—C6	−1.5 (2)	C11—C12—C13—C14	−0.4 (2)
C2—C1—C6—C5	−1.4 (2)	C12—C13—C14—C15	0.9 (3)
C2—C1—C6—C7	178.38 (13)	C13—C14—C15—C16	−0.3 (2)
C4—C5—C6—C1	1.7 (2)	C9—N3—C16—C15	−176.86 (16)
C4—C5—C6—C7	−178.10 (13)	C9—N3—C16—C11	0.99 (17)
N2—N1—C7—O4	2.7 (2)	C14—C15—C16—N3	176.83 (16)
N2—N1—C7—C6	−176.87 (12)	C14—C15—C16—C11	−0.8 (2)
C1—C6—C7—O4	18.6 (2)	C12—C11—C16—N3	−176.83 (14)
C5—C6—C7—O4	−161.64 (14)	C10—C11—C16—N3	−0.38 (17)
C1—C6—C7—N1	−161.86 (13)	C12—C11—C16—C15	1.2 (2)
C5—C6—C7—N1	17.9 (2)	C10—C11—C16—C15	177.65 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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···O3w^iv	0.86 (1)	1.94 (1)	2.760 (2)	161 (3)
O2w—H21···O3^v	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···O5w^vi	0.85 (1)	1.95 (1)	2.796 (2)	172 (3)
O3w—H32···O3^vii	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···O4^viii	0.84 (1)	2.37 (2)	2.921 (2)	124 (2)
O4w—H42···N2^viii	0.84 (1)	2.39 (1)	3.211 (2)	166 (2)
O5w—H51···O4w^ix	0.85 (1)	1.97 (1)	2.798 (2)	167 (2)
O5w—H52···O2w^x	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.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃N₃O₄·5H₂O
M_r	401.37
Crystal system, space group	Triclinic, 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)
V (Å³)	905.95 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.30 × 0.25 × 0.04

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7524, 4096, 3285
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.115, 1.05
No. of reflections	4096
No. of parameters	313
No. of restraints	15
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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···O3w^iv	0.86 (1)	1.94 (1)	2.760 (2)	161 (3)
O2w—H21···O3^v	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···O5w^vi	0.85 (1)	1.95 (1)	2.796 (2)	172 (3)
O3w—H32···O3^vii	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···O4^viii	0.84 (1)	2.37 (2)	2.921 (2)	124 (2)
O4w—H42···N2^viii	0.84 (1)	2.39 (1)	3.211 (2)	166 (2)
O5w—H51···O4w^ix	0.85 (1)	1.97 (1)	2.798 (2)	167 (2)
O5w—H52···O2w^x	0.85 (1)	1.97 (1)	2.810 (2)	168 (3)

Acknowledgements

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

References

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