3,4,5-Trihydr-oxy-N'-(1H-indol-3-yl-methyl-idene)benzohydrazide penta-hydrate.

The two aromatic parts of the title compound, C(16)H(13)N(3)O(4)·5H(2)O, are connected through a conjugated -CH=N-NH-C(O)- fragment, giving an almost planar mol-ecule. The organic mol-ecules and uncoordinated water mol-ecules 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 = 401.37

Triclinic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 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

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 ▶).

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

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

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

C16H13N3O4·5H2O	Z = 2
Mr = 401.37	F000 = 424
Triclinic, P1	Dx = 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 = 2.3–28.0º
c = 14.1966 (3) Å	µ = 0.12 mm−1
α = 103.814 (1)º	T = 100 (2) K
β = 103.716 (1)º	Plate, pale-yellow
γ = 90.613 (2)º	0.30 × 0.25 × 0.04 mm
V = 905.95 (4) Å3

Bruker SMART APEX diffractometer	3285 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Monochromator: graphite	θmax = 27.5º
T = 100(2) K	θmin = 2.3º
ω scans	h = −9→9
Absorption correction: None	k = −11→11
7524 measured reflections	l = −18→18
4096 independent reflections

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0613P)2 + 0.1789P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
4096 reflections	Δρmax = 0.35 e Å−3
313 parameters	Δρmin = −0.25 e Å−3
15 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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···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)

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⋯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) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) ; (ix) ; (x) .