3,4,5-Trihydr-oxy-N'-[(1-methyl-1H-indol-2-yl)methyl-idene]benzohydrazide.

The structure of the title compound, C(17)H(15)N(3)O(4), displays inter-molecular O-H⋯N and O-H⋯O hydrogen bonding between adjacent mol-ecules. Intra-molecular O-H⋯O hydrogen bonds also occur. The molecule is essentially planar with a deviation of 0.090 (1) Å from the best plane running through the connected ring systems.

Related literature

For related compounds see: Khaledi et al. (2008a ▶,b ▶, 2009 ▶).

Experimental

Crystal data

C17H15N3O4

M = 325.32

Monoclinic,

a = 9.0839 (2) Å

b = 13.1684 (3) Å

c = 12.4414 (3) Å

β = 104.2740 (10)°

V = 1442.30 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.49 × 0.16 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.948, T max = 0.991

10177 measured reflections

4070 independent reflections

3153 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.127

S = 0.99

4070 reflections

221 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.26 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: publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027032/hg2532sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027032/hg2532Isup2.hkl

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

C17H15N3O4	F(000) = 680
Mr = 325.32	Dx = 1.498 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3739 reflections
a = 9.0839 (2) Å	θ = 2.3–30.4°
b = 13.1684 (3) Å	µ = 0.11 mm−1
c = 12.4414 (3) Å	T = 100 K
β = 104.274 (1)°	Block, green
V = 1442.30 (6) Å3	0.49 × 0.16 × 0.09 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	4070 independent reflections
Radiation source: fine-focus sealed tube	3153 reflections with I > 2σ(I)
graphite	Rint = 0.019
ω scans	θmax = 30.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→12
Tmin = 0.948, Tmax = 0.991	k = −18→18
10177 measured reflections	l = −17→14

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0672P)2 + 0.9156P] where P = (Fo2 + 2Fc2)/3
4070 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
N1	0.47487 (13)	0.36671 (9)	0.05923 (10)	0.0132 (2)
H1N	0.4655	0.3333	−0.0034	0.016*
N2	0.38051 (13)	0.44784 (9)	0.06479 (10)	0.0134 (2)
N3	0.06173 (13)	0.56577 (9)	−0.13005 (10)	0.0151 (2)
O1	0.99391 (12)	0.12533 (8)	0.33141 (8)	0.0165 (2)
H1O	1.0219	0.0645	0.3313	0.025*
O2	0.98618 (11)	0.01716 (7)	0.13104 (8)	0.0149 (2)
H2O	0.9766	−0.0305	0.1737	0.022*
O3	0.77044 (12)	0.07206 (8)	−0.05744 (8)	0.0189 (2)
H3O	0.8473	0.0349	−0.0506	0.028*
O4	0.59664 (13)	0.38379 (8)	0.23996 (8)	0.0199 (2)
C1	0.04811 (18)	0.51469 (13)	−0.23489 (13)	0.0226 (3)
H1A	−0.0426	0.5393	−0.2887	0.034*
H1B	0.0393	0.4413	−0.2247	0.034*
H1C	0.1383	0.5288	−0.2623	0.034*
C2	−0.02892 (15)	0.64421 (11)	−0.11137 (12)	0.0155 (3)
C3	−0.15129 (16)	0.69271 (11)	−0.18421 (13)	0.0192 (3)
H3	−0.1834	0.6736	−0.2600	0.023*
C4	−0.22304 (17)	0.76936 (12)	−0.14091 (14)	0.0213 (3)
H4	−0.3059	0.8039	−0.1883	0.026*
C5	−0.17667 (17)	0.79760 (11)	−0.02853 (14)	0.0219 (3)
H5	−0.2291	0.8505	−0.0016	0.026*
C6	−0.05636 (17)	0.74988 (11)	0.04323 (13)	0.0195 (3)
H6	−0.0259	0.7692	0.1191	0.023*
C7	0.02010 (16)	0.67213 (11)	0.00177 (12)	0.0163 (3)
C8	0.14341 (16)	0.60759 (11)	0.05098 (12)	0.0162 (3)
H8	0.1997	0.6085	0.1263	0.019*
C9	0.16628 (15)	0.54349 (10)	−0.03077 (11)	0.0137 (3)
C10	0.27384 (15)	0.46201 (10)	−0.02389 (11)	0.0134 (3)
H10	0.2662	0.4180	−0.0856	0.016*
C11	0.58127 (15)	0.33924 (10)	0.15038 (11)	0.0129 (3)
C12	0.68091 (14)	0.25165 (10)	0.13972 (11)	0.0123 (3)
C13	0.78798 (15)	0.22437 (10)	0.23633 (11)	0.0132 (3)
H13	0.7917	0.2597	0.3035	0.016*
C14	0.88907 (15)	0.14590 (10)	0.23472 (11)	0.0128 (3)
C15	0.88441 (15)	0.09305 (10)	0.13689 (11)	0.0122 (2)
C16	0.77684 (15)	0.12083 (10)	0.04008 (11)	0.0135 (3)
C17	0.67475 (15)	0.19925 (10)	0.04105 (11)	0.0143 (3)
H17	0.6014	0.2171	−0.0249	0.017*

	U11	U22	U33	U12	U13	U23
N1	0.0140 (5)	0.0112 (5)	0.0140 (5)	0.0024 (4)	0.0029 (4)	−0.0013 (4)
N2	0.0120 (5)	0.0110 (5)	0.0173 (5)	0.0015 (4)	0.0040 (4)	0.0006 (4)
N3	0.0132 (5)	0.0141 (5)	0.0174 (6)	0.0019 (4)	0.0028 (4)	0.0011 (4)
O1	0.0180 (5)	0.0172 (5)	0.0121 (4)	0.0047 (4)	−0.0006 (4)	0.0011 (4)
O2	0.0183 (5)	0.0122 (5)	0.0157 (5)	0.0049 (4)	0.0069 (4)	0.0039 (4)
O3	0.0196 (5)	0.0214 (5)	0.0139 (5)	0.0075 (4)	0.0010 (4)	−0.0046 (4)
O4	0.0232 (5)	0.0203 (5)	0.0151 (5)	0.0068 (4)	0.0027 (4)	−0.0035 (4)
C1	0.0219 (7)	0.0248 (8)	0.0192 (7)	0.0035 (6)	0.0014 (6)	−0.0027 (6)
C2	0.0135 (6)	0.0124 (6)	0.0219 (7)	0.0001 (5)	0.0066 (5)	0.0025 (5)
C3	0.0148 (6)	0.0182 (7)	0.0247 (7)	0.0009 (5)	0.0050 (5)	0.0049 (6)
C4	0.0151 (6)	0.0168 (7)	0.0325 (8)	0.0031 (5)	0.0070 (6)	0.0071 (6)
C5	0.0185 (7)	0.0134 (6)	0.0370 (9)	0.0020 (5)	0.0128 (6)	0.0013 (6)
C6	0.0193 (7)	0.0154 (7)	0.0263 (8)	−0.0008 (5)	0.0101 (6)	−0.0018 (5)
C7	0.0149 (6)	0.0129 (6)	0.0220 (7)	−0.0004 (5)	0.0068 (5)	0.0009 (5)
C8	0.0155 (6)	0.0142 (6)	0.0197 (7)	0.0003 (5)	0.0061 (5)	0.0004 (5)
C9	0.0122 (6)	0.0123 (6)	0.0165 (6)	−0.0002 (5)	0.0034 (5)	0.0022 (5)
C10	0.0125 (6)	0.0126 (6)	0.0155 (6)	−0.0008 (5)	0.0042 (5)	−0.0007 (5)
C11	0.0134 (6)	0.0121 (6)	0.0135 (6)	0.0001 (5)	0.0042 (5)	0.0011 (5)
C12	0.0122 (6)	0.0116 (6)	0.0131 (6)	0.0007 (4)	0.0031 (5)	0.0013 (5)
C13	0.0148 (6)	0.0131 (6)	0.0120 (6)	0.0008 (5)	0.0034 (5)	−0.0004 (5)
C14	0.0131 (6)	0.0132 (6)	0.0117 (6)	0.0001 (5)	0.0022 (4)	0.0029 (5)
C15	0.0120 (6)	0.0111 (6)	0.0142 (6)	0.0012 (4)	0.0042 (5)	0.0020 (5)
C16	0.0147 (6)	0.0142 (6)	0.0120 (6)	0.0006 (5)	0.0038 (5)	−0.0016 (5)
C17	0.0142 (6)	0.0147 (6)	0.0129 (6)	0.0025 (5)	0.0013 (5)	0.0007 (5)

N1—C11	1.3455 (17)	C4—C5	1.407 (2)
N1—N2	1.3821 (15)	C4—H4	0.9500
N1—H1N	0.8800	C5—C6	1.380 (2)
N2—C10	1.2900 (17)	C5—H5	0.9500
N3—C2	1.3760 (18)	C6—C7	1.405 (2)
N3—C9	1.3912 (17)	C6—H6	0.9500
N3—C1	1.4455 (19)	C7—C8	1.419 (2)
O1—C14	1.3647 (16)	C8—C9	1.376 (2)
O1—H1O	0.8400	C8—H8	0.9500
O2—C15	1.3755 (16)	C9—C10	1.4394 (19)
O2—H2O	0.8400	C10—H10	0.9500
O3—C16	1.3613 (16)	C11—C12	1.4921 (18)
O3—H3O	0.8400	C12—C13	1.3941 (18)
O4—C11	1.2365 (17)	C12—C17	1.3972 (18)
C1—H1A	0.9800	C13—C14	1.3859 (18)
C1—H1B	0.9800	C13—H13	0.9500
C1—H1C	0.9800	C14—C15	1.3936 (18)
C2—C3	1.403 (2)	C15—C16	1.3995 (18)
C2—C7	1.416 (2)	C16—C17	1.3900 (19)
C3—C4	1.381 (2)	C17—H17	0.9500
C3—H3	0.9500
C11—N1—N2	119.41 (11)	C6—C7—C8	133.41 (14)
C11—N1—H1N	120.3	C2—C7—C8	107.14 (12)
N2—N1—H1N	120.3	C9—C8—C7	107.18 (13)
C10—N2—N1	114.41 (11)	C9—C8—H8	126.4
C2—N3—C9	108.32 (12)	C7—C8—H8	126.4
C2—N3—C1	125.46 (12)	C8—C9—N3	109.41 (12)
C9—N3—C1	126.22 (12)	C8—C9—C10	129.58 (13)
C14—O1—H1O	109.5	N3—C9—C10	120.98 (12)
C15—O2—H2O	109.5	N2—C10—C9	120.95 (13)
C16—O3—H3O	109.5	N2—C10—H10	119.5
N3—C1—H1A	109.5	C9—C10—H10	119.5
N3—C1—H1B	109.5	O4—C11—N1	122.01 (12)
H1A—C1—H1B	109.5	O4—C11—C12	120.71 (12)
N3—C1—H1C	109.5	N1—C11—C12	117.28 (12)
H1A—C1—H1C	109.5	C13—C12—C17	119.91 (12)
H1B—C1—H1C	109.5	C13—C12—C11	115.60 (12)
N3—C2—C3	130.13 (14)	C17—C12—C11	124.48 (12)
N3—C2—C7	107.95 (12)	C14—C13—C12	120.23 (12)
C3—C2—C7	121.92 (13)	C14—C13—H13	119.9
C4—C3—C2	117.12 (14)	C12—C13—H13	119.9
C4—C3—H3	121.4	O1—C14—C13	117.13 (12)
C2—C3—H3	121.4	O1—C14—C15	122.35 (12)
C3—C4—C5	121.76 (14)	C13—C14—C15	120.49 (12)
C3—C4—H4	119.1	O2—C15—C14	122.20 (12)
C5—C4—H4	119.1	O2—C15—C16	118.70 (12)
C6—C5—C4	121.17 (14)	C14—C15—C16	119.04 (12)
C6—C5—H5	119.4	O3—C16—C17	118.44 (12)
C4—C5—H5	119.4	O3—C16—C15	120.73 (12)
C5—C6—C7	118.60 (15)	C17—C16—C15	120.83 (12)
C5—C6—H6	120.7	C16—C17—C12	119.49 (12)
C7—C6—H6	120.7	C16—C17—H17	120.3
C6—C7—C2	119.43 (13)	C12—C17—H17	120.3
C11—N1—N2—C10	−173.94 (12)	C8—C9—C10—N2	−9.1 (2)
C9—N3—C2—C3	−179.04 (14)	N3—C9—C10—N2	172.91 (13)
C1—N3—C2—C3	0.1 (2)	N2—N1—C11—O4	0.8 (2)
C9—N3—C2—C7	0.29 (15)	N2—N1—C11—C12	−179.57 (11)
C1—N3—C2—C7	179.39 (13)	O4—C11—C12—C13	0.73 (19)
N3—C2—C3—C4	179.14 (14)	N1—C11—C12—C13	−178.95 (12)
C7—C2—C3—C4	−0.1 (2)	O4—C11—C12—C17	−177.78 (13)
C2—C3—C4—C5	−0.4 (2)	N1—C11—C12—C17	2.5 (2)
C3—C4—C5—C6	0.3 (2)	C17—C12—C13—C14	0.5 (2)
C4—C5—C6—C7	0.2 (2)	C11—C12—C13—C14	−178.13 (12)
C5—C6—C7—C2	−0.7 (2)	C12—C13—C14—O1	177.99 (12)
C5—C6—C7—C8	−178.83 (15)	C12—C13—C14—C15	−0.4 (2)
N3—C2—C7—C6	−178.74 (13)	O1—C14—C15—O2	−0.6 (2)
C3—C2—C7—C6	0.7 (2)	C13—C14—C15—O2	177.66 (12)
N3—C2—C7—C8	−0.15 (16)	O1—C14—C15—C16	−177.82 (12)
C3—C2—C7—C8	179.24 (13)	C13—C14—C15—C16	0.4 (2)
C6—C7—C8—C9	178.27 (16)	O2—C15—C16—O3	1.6 (2)
C2—C7—C8—C9	−0.04 (16)	C14—C15—C16—O3	178.93 (12)
C7—C8—C9—N3	0.22 (16)	O2—C15—C16—C17	−177.94 (12)
C7—C8—C9—C10	−177.98 (14)	C14—C15—C16—C17	−0.6 (2)
C2—N3—C9—C8	−0.32 (16)	O3—C16—C17—C12	−178.85 (12)
C1—N3—C9—C8	−179.42 (13)	C15—C16—C17—C12	0.7 (2)
C2—N3—C9—C10	178.06 (12)	C13—C12—C17—C16	−0.6 (2)
C1—N3—C9—C10	−1.0 (2)	C11—C12—C17—C16	177.82 (13)
N1—N2—C10—C9	179.93 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O4i	0.84	1.80	2.6119 (14)	164
O1—H1O···N2i	0.84	2.06	2.7759 (15)	142
O3—H3O···O2ii	0.84	2.12	2.8469 (14)	144
O1—H1O···O2	0.84	2.51	2.8570 (14)	106
O3—H3O···O2	0.84	2.31	2.7560 (14)	113

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O4i	0.84	1.80	2.6119 (14)	164
O1—H1O⋯N2i	0.84	2.06	2.7759 (15)	142
O3—H3O⋯O2ii	0.84	2.12	2.8469 (14)	144
O1—H1O⋯O2	0.84	2.51	2.8570 (14)	106
O3—H3O⋯O2	0.84	2.31	2.7560 (14)	113

Symmetry codes: (i) ; (ii) .