N'-(2-Chloro-benzyl-idene)-3,4,5-tri-methoxy-benzohydrazide methanol solvate.

In the title compound, C(17)H(17)ClN(2)O(4)·CH(4)O, the dihedral angle between the benzene ring planes is 5.29 (6)°. Inter-molecular N-H⋯O and O-H⋯O hydrogen bonds link the mol-ecules into a chain along the a axis.

Related literature

For related literature, see: Allen et al. (1987 ▶), Bernardino et al. (2006 ▶); Ganjali et al. (2006 ▶); Gardner et al. (1991 ▶); Patole et al. (2003 ▶)

Experimental

Crystal data

C17H17ClN2O4·CH4O

M = 380.82

Orthorhombic,

a = 12.9356 (7) Å

b = 4.8718 (3) Å

c = 29.4119 (16) Å

V = 1853.53 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 173 (2) K

0.48 × 0.40 × 0.39 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.895, T max = 0.913

9008 measured reflections

3916 independent reflections

3561 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.080

S = 1.09

3916 reflections

240 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.17 e Å−3

Absolute structure: Flack (1983 ▶), 1846 Friedel pairs

Flack parameter: 0.04 (5)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536808023891/hb2761sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023891/hb2761Isup2.hkl

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

C17H17ClN2O4·CH4O	F000 = 800
Mr = 380.82	Dx = 1.365 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5318 reflections
a = 12.9356 (7) Å	θ = 2.6–27.0º
b = 4.8718 (3) Å	µ = 0.24 mm−1
c = 29.4119 (16) Å	T = 173 (2) K
V = 1853.53 (18) Å3	Block, colorless
Z = 4	0.48 × 0.40 × 0.39 mm

Bruker SMART 1000 CCD diffractometer	3916 independent reflections
Radiation source: fine-focus sealed tube	3561 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.021
T = 173(2) K	θmax = 27.0º
ω scans	θmin = 2.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)	h = −16→8
Tmin = 0.895, Tmax = 0.913	k = −5→6
9008 measured reflections	l = −37→36

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031	w = 1/[σ2(Fo2) + (0.039P)2 + 0.3064P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.080	(Δ/σ)max = 0.012
S = 1.09	Δρmax = 0.20 e Å−3
3916 reflections	Δρmin = −0.17 e Å−3
240 parameters	Extinction correction: none
1 restraint	Absolute structure: Flack (1983), 1846 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (5)
Secondary atom site location: difference Fourier map

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
Cl1	0.88399 (4)	−0.29291 (12)	0.98890 (2)	0.04522 (15)
C1	0.93423 (13)	0.2105 (4)	0.75620 (6)	0.0215 (3)
C2	0.85309 (13)	0.0229 (4)	0.75340 (6)	0.0211 (3)
H2	0.8352	−0.0866	0.7789	0.025*
C3	0.79858 (12)	−0.0025 (3)	0.71285 (6)	0.0213 (3)
C4	0.82468 (13)	0.1595 (3)	0.67522 (6)	0.0209 (3)
C5	0.90935 (13)	0.3386 (4)	0.67796 (6)	0.0221 (3)
C6	0.96347 (13)	0.3656 (4)	0.71860 (6)	0.0216 (3)
H6	1.0201	0.4892	0.7207	0.026*
C7	0.99585 (13)	0.2484 (4)	0.79886 (6)	0.0231 (4)
C8	0.96354 (14)	0.0864 (4)	0.91319 (7)	0.0308 (4)
H8	0.8949	0.0174	0.9121	0.037*
C9	1.02227 (15)	0.0827 (4)	0.95597 (6)	0.0286 (4)
C10	0.99287 (15)	−0.0824 (4)	0.99280 (7)	0.0319 (4)
C11	1.04956 (19)	−0.0869 (5)	1.03275 (7)	0.0403 (5)
H11	1.0289	−0.2029	1.0571	0.048*
C12	1.13525 (18)	0.0753 (5)	1.03723 (7)	0.0435 (5)
H12	1.1731	0.0753	1.0649	0.052*
C13	1.16701 (18)	0.2405 (5)	1.00118 (7)	0.0416 (5)
H13	1.2270	0.3517	1.0041	0.050*
C14	1.11093 (16)	0.2419 (5)	0.96120 (7)	0.0362 (5)
H14	1.1334	0.3541	0.9367	0.043*
C15	0.69115 (15)	−0.3585 (4)	0.74240 (6)	0.0260 (4)
H15A	0.7517	−0.4661	0.7515	0.039*
H15B	0.6361	−0.4827	0.7324	0.039*
H15C	0.6668	−0.2497	0.7683	0.039*
C16	0.71561 (18)	0.3559 (4)	0.61922 (7)	0.0386 (5)
H16A	0.6581	0.3954	0.6399	0.058*
H16B	0.6884	0.3175	0.5888	0.058*
H16C	0.7619	0.5150	0.6179	0.058*
C17	1.01472 (14)	0.6703 (4)	0.63995 (7)	0.0302 (4)
H17A	0.9989	0.8111	0.6627	0.045*
H17B	1.0217	0.7565	0.6100	0.045*
H17C	1.0796	0.5785	0.6480	0.045*
C18	1.2215 (2)	0.7735 (5)	0.86998 (9)	0.0501 (6)
H18A	1.1903	0.7780	0.9003	0.075*
H18B	1.1739	0.8569	0.8480	0.075*
H18C	1.2866	0.8763	0.8703	0.075*
N1	0.94896 (12)	0.1728 (3)	0.83814 (5)	0.0268 (3)
H1	0.8841	0.1185	0.8385	0.032*
N2	1.00645 (11)	0.1840 (3)	0.87756 (5)	0.0269 (3)
O1	0.71872 (9)	−0.1791 (3)	0.70587 (4)	0.0259 (3)
O2	0.77131 (9)	0.1235 (3)	0.63530 (4)	0.0259 (3)
O3	0.93290 (10)	0.4729 (3)	0.63872 (4)	0.0308 (3)
O4	1.08391 (10)	0.3399 (3)	0.79778 (4)	0.0298 (3)
O5	1.24118 (9)	0.4964 (3)	0.85732 (5)	0.0328 (3)
H5	1.1900	0.4338	0.8431	0.049*

	U11	U22	U33	U12	U13	U23
Cl1	0.0469 (3)	0.0485 (3)	0.0403 (3)	−0.0043 (2)	0.0087 (2)	0.0094 (3)
C1	0.0212 (8)	0.0249 (9)	0.0183 (8)	0.0027 (7)	−0.0023 (7)	−0.0007 (7)
C2	0.0216 (8)	0.0220 (8)	0.0196 (8)	0.0027 (6)	0.0005 (7)	0.0018 (7)
C3	0.0197 (8)	0.0211 (8)	0.0231 (8)	0.0018 (6)	0.0002 (7)	−0.0038 (7)
C4	0.0212 (8)	0.0242 (9)	0.0171 (8)	0.0044 (7)	−0.0033 (6)	−0.0027 (6)
C5	0.0219 (8)	0.0239 (9)	0.0205 (8)	0.0015 (7)	0.0007 (6)	0.0009 (7)
C6	0.0205 (8)	0.0243 (8)	0.0201 (8)	−0.0005 (7)	−0.0017 (6)	−0.0003 (7)
C7	0.0219 (8)	0.0280 (9)	0.0195 (8)	0.0017 (7)	−0.0028 (7)	−0.0007 (7)
C8	0.0255 (9)	0.0425 (11)	0.0244 (9)	−0.0010 (8)	−0.0022 (7)	0.0010 (8)
C9	0.0308 (10)	0.0370 (10)	0.0179 (8)	0.0040 (8)	−0.0003 (7)	−0.0002 (8)
C10	0.0353 (10)	0.0339 (10)	0.0266 (9)	0.0074 (8)	0.0055 (8)	−0.0001 (8)
C11	0.0580 (14)	0.0406 (12)	0.0221 (9)	0.0135 (11)	0.0047 (9)	0.0069 (9)
C12	0.0540 (14)	0.0538 (14)	0.0227 (9)	0.0139 (11)	−0.0115 (9)	−0.0045 (10)
C13	0.0419 (12)	0.0519 (14)	0.0309 (11)	0.0028 (10)	−0.0109 (9)	−0.0042 (10)
C14	0.0397 (11)	0.0458 (12)	0.0233 (9)	−0.0009 (10)	−0.0031 (8)	0.0043 (9)
C15	0.0269 (9)	0.0232 (9)	0.0278 (9)	−0.0019 (7)	0.0025 (7)	−0.0004 (7)
C16	0.0433 (12)	0.0374 (11)	0.0351 (11)	0.0081 (10)	−0.0179 (9)	−0.0010 (9)
C17	0.0269 (9)	0.0345 (10)	0.0293 (9)	−0.0029 (8)	−0.0006 (8)	0.0078 (8)
C18	0.0638 (15)	0.0453 (13)	0.0412 (13)	0.0120 (12)	−0.0099 (12)	−0.0078 (11)
N1	0.0206 (7)	0.0415 (9)	0.0184 (7)	−0.0044 (6)	−0.0041 (6)	0.0019 (6)
N2	0.0257 (7)	0.0370 (9)	0.0180 (7)	0.0010 (6)	−0.0053 (6)	0.0009 (6)
O1	0.0263 (6)	0.0282 (7)	0.0232 (6)	−0.0049 (5)	−0.0047 (5)	0.0008 (5)
O2	0.0292 (6)	0.0276 (6)	0.0208 (6)	0.0011 (5)	−0.0064 (5)	−0.0028 (5)
O3	0.0309 (6)	0.0399 (7)	0.0217 (6)	−0.0096 (6)	−0.0052 (6)	0.0076 (6)
O4	0.0243 (6)	0.0426 (8)	0.0225 (7)	−0.0089 (6)	−0.0040 (5)	0.0029 (6)
O5	0.0231 (6)	0.0405 (7)	0.0347 (7)	0.0025 (6)	−0.0042 (5)	−0.0078 (6)

Cl1—C10	1.746 (2)	C12—H12	0.9500
C1—C6	1.392 (2)	C13—C14	1.382 (3)
C1—C2	1.394 (2)	C13—H13	0.9500
C1—C7	1.498 (2)	C14—H14	0.9500
C2—C3	1.391 (2)	C15—O1	1.430 (2)
C2—H2	0.9500	C15—H15A	0.9800
C3—O1	1.360 (2)	C15—H15B	0.9800
C3—C4	1.401 (2)	C15—H15C	0.9800
C4—O2	1.373 (2)	C16—O2	1.423 (2)
C4—C5	1.402 (2)	C16—H16A	0.9800
C5—O3	1.361 (2)	C16—H16B	0.9800
C5—C6	1.391 (2)	C16—H16C	0.9800
C6—H6	0.9500	C17—O3	1.430 (2)
C7—O4	1.224 (2)	C17—H17A	0.9800
C7—N1	1.356 (2)	C17—H17B	0.9800
C8—N2	1.278 (2)	C17—H17C	0.9800
C8—C9	1.470 (2)	C18—O5	1.423 (3)
C8—H8	0.9500	C18—H18A	0.9800
C9—C14	1.393 (3)	C18—H18B	0.9800
C9—C10	1.402 (3)	C18—H18C	0.9800
C10—C11	1.385 (3)	N1—N2	1.378 (2)
C11—C12	1.368 (3)	N1—H1	0.8800
C11—H11	0.9500	O5—H5	0.8400
C12—C13	1.393 (3)
C6—C1—C2	120.90 (15)	C14—C13—H13	120.1
C6—C1—C7	117.00 (15)	C12—C13—H13	120.1
C2—C1—C7	122.07 (14)	C13—C14—C9	121.6 (2)
C3—C2—C1	119.38 (15)	C13—C14—H14	119.2
C3—C2—H2	120.3	C9—C14—H14	119.2
C1—C2—H2	120.3	O1—C15—H15A	109.5
O1—C3—C2	124.80 (15)	O1—C15—H15B	109.5
O1—C3—C4	114.85 (15)	H15A—C15—H15B	109.5
C2—C3—C4	120.34 (15)	O1—C15—H15C	109.5
O2—C4—C3	118.83 (15)	H15A—C15—H15C	109.5
O2—C4—C5	121.43 (15)	H15B—C15—H15C	109.5
C3—C4—C5	119.55 (14)	O2—C16—H16A	109.5
O3—C5—C6	124.76 (15)	O2—C16—H16B	109.5
O3—C5—C4	115.15 (14)	H16A—C16—H16B	109.5
C6—C5—C4	120.09 (15)	O2—C16—H16C	109.5
C5—C6—C1	119.63 (16)	H16A—C16—H16C	109.5
C5—C6—H6	120.2	H16B—C16—H16C	109.5
C1—C6—H6	120.2	O3—C17—H17A	109.5
O4—C7—N1	122.52 (16)	O3—C17—H17B	109.5
O4—C7—C1	121.23 (15)	H17A—C17—H17B	109.5
N1—C7—C1	116.24 (15)	O3—C17—H17C	109.5
N2—C8—C9	118.82 (17)	H17A—C17—H17C	109.5
N2—C8—H8	120.6	H17B—C17—H17C	109.5
C9—C8—H8	120.6	O5—C18—H18A	109.5
C14—C9—C10	117.21 (17)	O5—C18—H18B	109.5
C14—C9—C8	120.89 (18)	H18A—C18—H18B	109.5
C10—C9—C8	121.89 (18)	O5—C18—H18C	109.5
C11—C10—C9	121.40 (19)	H18A—C18—H18C	109.5
C11—C10—Cl1	118.27 (16)	H18B—C18—H18C	109.5
C9—C10—Cl1	120.33 (15)	C7—N1—N2	117.68 (14)
C12—C11—C10	120.1 (2)	C7—N1—H1	121.2
C12—C11—H11	119.9	N2—N1—H1	121.2
C10—C11—H11	119.9	C8—N2—N1	116.16 (15)
C11—C12—C13	119.97 (19)	C3—O1—C15	117.56 (13)
C11—C12—H12	120.0	C4—O2—C16	115.90 (14)
C13—C12—H12	120.0	C5—O3—C17	117.86 (14)
C14—C13—C12	119.7 (2)	C18—O5—H5	109.5
C6—C1—C2—C3	−2.2 (2)	C14—C9—C10—C11	0.1 (3)
C7—C1—C2—C3	179.86 (15)	C8—C9—C10—C11	179.16 (19)
C1—C2—C3—O1	179.51 (15)	C14—C9—C10—Cl1	−178.94 (15)
C1—C2—C3—C4	−0.2 (2)	C8—C9—C10—Cl1	0.2 (3)
O1—C3—C4—O2	−1.7 (2)	C9—C10—C11—C12	1.1 (3)
C2—C3—C4—O2	178.07 (15)	Cl1—C10—C11—C12	−179.86 (17)
O1—C3—C4—C5	−176.74 (15)	C10—C11—C12—C13	−1.5 (3)
C2—C3—C4—C5	3.0 (2)	C11—C12—C13—C14	0.7 (3)
O2—C4—C5—O3	0.7 (2)	C12—C13—C14—C9	0.5 (3)
C3—C4—C5—O3	175.62 (15)	C10—C9—C14—C13	−0.8 (3)
O2—C4—C5—C6	−178.40 (16)	C8—C9—C14—C13	−180.0 (2)
C3—C4—C5—C6	−3.5 (2)	O4—C7—N1—N2	−4.4 (3)
O3—C5—C6—C1	−177.87 (16)	C1—C7—N1—N2	174.82 (16)
C4—C5—C6—C1	1.1 (3)	C9—C8—N2—N1	177.74 (17)
C2—C1—C6—C5	1.7 (3)	C7—N1—N2—C8	−173.39 (17)
C7—C1—C6—C5	179.79 (15)	C2—C3—O1—C15	−2.3 (2)
C6—C1—C7—O4	−21.9 (3)	C4—C3—O1—C15	177.43 (14)
C2—C1—C7—O4	156.15 (17)	C3—C4—O2—C16	118.71 (19)
C6—C1—C7—N1	158.87 (16)	C5—C4—O2—C16	−66.3 (2)
C2—C1—C7—N1	−23.1 (2)	C6—C5—O3—C17	−4.5 (3)
N2—C8—C9—C14	16.3 (3)	C4—C5—O3—C17	176.48 (15)
N2—C8—C9—C10	−162.78 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5i	0.88	2.01	2.8673 (19)	165
O5—H5···O4	0.84	1.97	2.7904 (18)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5i	0.88	2.01	2.8673 (19)	165
O5—H5⋯O4	0.84	1.97	2.7904 (18)	166

Symmetry code: (i) .