(E)-N′-[4-(4-Chloro­benz­yloxy)-3-methoxybenzyl­idene]thio­phene-2-carbohydrazide

In the title compound, C₂₀H₁₇ClN₂O₃S, the vanillin group makes dihedral angles of 73.65 (11) and 2.16 (16)° with the chloro-substituted ­benzene ring and the thio­phene mean plane, respectively. The crystal packing is stabilized by an inter­molecular N—H...O hydrogen bond that forms a centrosymmetric dimer.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.056
• wR factor = 0.176
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C6
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.10
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(E)—N'-[4-(4-Chlorobenzyloxy)-3-methoxybenzylidene]thiophene-2-carbohydrazide

Crystal data

C20H17ClN2O3S	Z = 2
Mr = 400.88	F(000) = 416
Triclinic, P1	Dx = 1.424 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.275 (3) Å	Cell parameters from 2127 reflections
b = 9.884 (3) Å	θ = 2.5–24.6°
c = 11.584 (3) Å	µ = 0.34 mm^−1
α = 89.503 (5)°	T = 294 K
β = 81.062 (5)°	Block, colourless
γ = 86.951 (5)°	0.14 × 0.12 × 0.08 mm
V = 934.6 (5) Å^3

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3264 independent reflections
Radiation source: fine-focus sealed tube	1803 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
Tmin = 0.931, Tmax = 0.973	k = −11→9
4778 measured reflections	l = −13→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.176	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0663P)^2 + 0.5087P] where P = (Fo^2 + 2Fc^2)/3
3264 reflections	(Δ/σ)max < 0.001
246 parameters	Δρmax = 0.39 e Å^−3
6 restraints	Δρmin = −0.39 e Å^−3

Special details

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 > 2σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	1.32387 (16)	1.21499 (12)	0.22251 (12)	0.0502 (4)
Cl1	0.6607 (3)	0.06608 (18)	0.57963 (17)	0.1240 (9)
O1	0.7948 (4)	0.6408 (3)	0.2918 (3)	0.0476 (9)
O2	0.5900 (4)	0.7551 (3)	0.1665 (3)	0.0477 (9)
O3	1.1892 (4)	1.5373 (3)	0.0465 (3)	0.0566 (10)
N1	1.0441 (4)	1.2169 (3)	0.1153 (3)	0.0383 (9)
N2	1.0575 (4)	1.3453 (3)	0.0697 (3)	0.0432 (10)
H2	0.9845	1.3781	0.0304	0.052*
C1	0.7016 (7)	0.4593 (5)	0.5230 (5)	0.0573 (14)
H1	0.6519	0.5399	0.5552	0.069*
C2	0.6489 (7)	0.3381 (6)	0.5694 (5)	0.0622 (15)
H2A	0.5632	0.3360	0.6316	0.075*
C3	0.7246 (8)	0.2214 (5)	0.5226 (5)	0.0592 (15)
C4	0.8501 (8)	0.2227 (5)	0.4313 (5)	0.0647 (16)
H4	0.9006	0.1419	0.4003	0.078*
C5	0.9007 (6)	0.3439 (5)	0.3858 (4)	0.0555 (14)
H5	0.9871	0.3453	0.3240	0.067*
C6	0.8261 (6)	0.4638 (5)	0.4299 (4)	0.0457 (12)
C7	0.8864 (8)	0.5959 (5)	0.3807 (5)	0.0770 (19)
H7A	0.8745	0.6632	0.4423	0.092*
H7B	1.0016	0.5846	0.3482	0.092*
C8	0.8346 (6)	0.7647 (4)	0.2430 (4)	0.0405 (11)
C9	0.9754 (6)	0.8273 (5)	0.2552 (4)	0.0523 (13)
H9	1.0512	0.7844	0.2966	0.063*
C10	1.0055 (6)	0.9530 (4)	0.2064 (4)	0.0463 (12)
H10	1.1012	0.9941	0.2156	0.056*
C11	0.8952 (5)	1.0187 (4)	0.1441 (4)	0.0362 (10)
C12	0.7538 (5)	0.9526 (4)	0.1296 (4)	0.0386 (11)
H12	0.6791	0.9949	0.0870	0.046*
C13	0.7228 (5)	0.8264 (4)	0.1771 (4)	0.0364 (11)
C14	0.4664 (6)	0.8191 (5)	0.1089 (4)	0.0519 (13)
H14A	0.4309	0.9045	0.1456	0.078*
H14B	0.3750	0.7622	0.1140	0.078*
H14C	0.5099	0.8336	0.0283	0.078*
C15	0.9201 (5)	1.1545 (4)	0.0957 (4)	0.0373 (11)
H15	0.8464	1.1949	0.0512	0.045*
C16	1.1833 (5)	1.4211 (4)	0.0855 (4)	0.0420 (11)
C17	1.3156 (5)	1.3663 (4)	0.1475 (4)	0.0387 (11)
C18	1.4525 (6)	1.4355 (5)	0.1535 (4)	0.0465 (12)
H18	1.4707	1.5196	0.1185	0.056*
C19	1.5625 (6)	1.3682 (5)	0.2171 (4)	0.0552 (14)
H19	1.6617	1.4018	0.2287	0.066*
C20	1.5080 (6)	1.2482 (5)	0.2600 (4)	0.0551 (14)
H20	1.5651	1.1904	0.3051	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0477 (8)	0.0395 (7)	0.0668 (9)	−0.0068 (5)	−0.0190 (6)	0.0183 (6)
Cl1	0.198 (2)	0.0748 (11)	0.1198 (16)	−0.0761 (13)	−0.0692 (15)	0.0521 (11)
O1	0.051 (2)	0.0386 (17)	0.061 (2)	−0.0157 (15)	−0.0294 (16)	0.0230 (15)
O2	0.044 (2)	0.0375 (17)	0.068 (2)	−0.0165 (14)	−0.0271 (17)	0.0191 (16)
O3	0.055 (2)	0.0323 (17)	0.089 (3)	−0.0152 (15)	−0.0265 (19)	0.0251 (17)
N1	0.040 (2)	0.0273 (19)	0.048 (2)	−0.0081 (16)	−0.0095 (18)	0.0094 (17)
N2	0.042 (2)	0.0308 (19)	0.061 (3)	−0.0109 (17)	−0.0193 (19)	0.0173 (18)
C1	0.060 (4)	0.048 (3)	0.065 (4)	0.004 (3)	−0.018 (3)	0.006 (3)
C2	0.054 (4)	0.079 (4)	0.053 (4)	−0.015 (3)	−0.003 (3)	0.014 (3)
C3	0.087 (4)	0.047 (3)	0.053 (3)	−0.026 (3)	−0.033 (3)	0.020 (3)
C4	0.092 (5)	0.047 (3)	0.059 (4)	0.009 (3)	−0.028 (3)	−0.005 (3)
C5	0.055 (3)	0.070 (4)	0.041 (3)	−0.002 (3)	−0.004 (2)	0.007 (3)
C6	0.051 (3)	0.051 (3)	0.041 (3)	−0.013 (2)	−0.022 (2)	0.017 (2)
C7	0.095 (5)	0.067 (4)	0.086 (4)	−0.034 (3)	−0.061 (4)	0.046 (3)
C8	0.046 (3)	0.032 (2)	0.048 (3)	−0.011 (2)	−0.018 (2)	0.011 (2)
C9	0.049 (3)	0.043 (3)	0.072 (4)	−0.011 (2)	−0.031 (3)	0.020 (3)
C10	0.042 (3)	0.036 (2)	0.068 (3)	−0.012 (2)	−0.025 (2)	0.012 (2)
C11	0.041 (3)	0.029 (2)	0.038 (3)	−0.0081 (19)	−0.007 (2)	0.0034 (19)
C12	0.039 (3)	0.033 (2)	0.046 (3)	−0.0025 (19)	−0.013 (2)	0.006 (2)
C13	0.035 (3)	0.034 (2)	0.043 (3)	−0.0094 (19)	−0.011 (2)	0.009 (2)
C14	0.042 (3)	0.044 (3)	0.075 (4)	−0.009 (2)	−0.027 (3)	0.011 (3)
C15	0.041 (3)	0.032 (2)	0.041 (3)	−0.006 (2)	−0.010 (2)	0.005 (2)
C16	0.039 (3)	0.035 (3)	0.053 (3)	−0.006 (2)	−0.011 (2)	0.010 (2)
C17	0.040 (3)	0.034 (2)	0.044 (3)	−0.008 (2)	−0.009 (2)	0.007 (2)
C18	0.047 (3)	0.040 (3)	0.054 (3)	−0.011 (2)	−0.011 (2)	0.003 (2)
C19	0.043 (3)	0.060 (3)	0.068 (4)	−0.010 (3)	−0.022 (3)	−0.001 (3)
C20	0.048 (3)	0.058 (3)	0.064 (4)	0.001 (2)	−0.025 (3)	0.005 (3)

Geometric parameters (Å, º)

S1—C20	1.697 (5)	C7—H7A	0.9700
S1—C17	1.727 (4)	C7—H7B	0.9700
Cl1—C3	1.741 (5)	C8—C9	1.375 (6)
O1—C8	1.379 (5)	C8—C13	1.400 (6)
O1—C7	1.425 (5)	C9—C10	1.379 (6)
O2—C13	1.359 (5)	C9—H9	0.9300
O2—C14	1.424 (5)	C10—C11	1.382 (6)
O3—C16	1.232 (5)	C10—H10	0.9300
N1—C15	1.275 (5)	C11—C12	1.403 (6)
N1—N2	1.374 (4)	C11—C15	1.463 (5)
N2—C16	1.350 (5)	C12—C13	1.379 (5)
N2—H2	0.8600	C12—H12	0.9300
C1—C6	1.373 (7)	C14—H14A	0.9600
C1—C2	1.373 (7)	C14—H14B	0.9600
C1—H1	0.9300	C14—H14C	0.9600
C2—C3	1.359 (8)	C15—H15	0.9300
C2—H2A	0.9300	C16—C17	1.476 (6)
C3—C4	1.363 (8)	C17—C18	1.365 (6)
C4—C5	1.365 (7)	C18—C19	1.397 (6)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.372 (7)	C19—C20	1.354 (6)
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.499 (6)	C20—H20	0.9300
C20—S1—C17	91.5 (2)	C9—C10—C11	120.9 (4)
C8—O1—C7	115.2 (3)	C9—C10—H10	119.6
C13—O2—C14	117.7 (3)	C11—C10—H10	119.6
C15—N1—N2	116.0 (4)	C10—C11—C12	118.1 (4)
C16—N2—N1	121.2 (4)	C10—C11—C15	122.2 (4)
C16—N2—H2	119.4	C12—C11—C15	119.7 (4)
N1—N2—H2	119.4	C13—C12—C11	121.6 (4)
C6—C1—C2	121.3 (5)	C13—C12—H12	119.2
C6—C1—H1	119.4	C11—C12—H12	119.2
C2—C1—H1	119.4	O2—C13—C12	125.4 (4)
C3—C2—C1	118.6 (5)	O2—C13—C8	115.9 (4)
C3—C2—H2A	120.7	C12—C13—C8	118.7 (4)
C1—C2—H2A	120.7	O2—C14—H14A	109.5
C2—C3—C4	121.4 (5)	O2—C14—H14B	109.5
C2—C3—Cl1	119.7 (5)	H14A—C14—H14B	109.5
C4—C3—Cl1	118.9 (5)	O2—C14—H14C	109.5
C3—C4—C5	119.3 (5)	H14A—C14—H14C	109.5
C3—C4—H4	120.4	H14B—C14—H14C	109.5
C5—C4—H4	120.4	N1—C15—C11	119.2 (4)
C4—C5—C6	120.9 (5)	N1—C15—H15	120.4
C4—C5—H5	119.5	C11—C15—H15	120.4
C6—C5—H5	119.5	O3—C16—N2	119.6 (4)
C5—C6—C1	118.4 (5)	O3—C16—C17	119.3 (4)
C5—C6—C7	120.1 (5)	N2—C16—C17	121.1 (4)
C1—C6—C7	121.4 (5)	C18—C17—C16	122.0 (4)
O1—C7—C6	109.7 (4)	C18—C17—S1	110.2 (3)
O1—C7—H7A	109.7	C16—C17—S1	127.8 (3)
C6—C7—H7A	109.7	C17—C18—C19	113.6 (4)
O1—C7—H7B	109.7	C17—C18—H18	123.2
C6—C7—H7B	109.7	C19—C18—H18	123.2
H7A—C7—H7B	108.2	C20—C19—C18	112.1 (4)
C9—C8—O1	123.7 (4)	C20—C19—H19	124.0
C9—C8—C13	120.0 (4)	C18—C19—H19	124.0
O1—C8—C13	116.3 (4)	C19—C20—S1	112.5 (4)
C8—C9—C10	120.6 (4)	C19—C20—H20	123.7
C8—C9—H9	119.7	S1—C20—H20	123.7
C10—C9—H9	119.7
C15—N1—N2—C16	179.6 (4)	C14—O2—C13—C8	174.7 (4)
C6—C1—C2—C3	1.1 (8)	C11—C12—C13—O2	−179.5 (4)
C1—C2—C3—C4	−0.2 (8)	C11—C12—C13—C8	1.2 (7)
C1—C2—C3—Cl1	180.0 (4)	C9—C8—C13—O2	177.8 (4)
C2—C3—C4—C5	0.0 (8)	O1—C8—C13—O2	−1.7 (6)
Cl1—C3—C4—C5	179.8 (4)	C9—C8—C13—C12	−2.7 (7)
C3—C4—C5—C6	−0.7 (8)	O1—C8—C13—C12	177.8 (4)
C4—C5—C6—C1	1.6 (7)	N2—N1—C15—C11	−178.4 (4)
C4—C5—C6—C7	178.4 (4)	C10—C11—C15—N1	−2.8 (7)
C2—C1—C6—C5	−1.8 (7)	C12—C11—C15—N1	175.9 (4)
C2—C1—C6—C7	−178.6 (5)	N1—N2—C16—O3	−177.8 (4)
C8—O1—C7—C6	177.4 (4)	N1—N2—C16—C17	3.0 (7)
C5—C6—C7—O1	93.8 (6)	O3—C16—C17—C18	−6.4 (7)
C1—C6—C7—O1	−89.4 (6)	N2—C16—C17—C18	172.8 (4)
C7—O1—C8—C9	15.4 (7)	O3—C16—C17—S1	172.5 (4)
C7—O1—C8—C13	−165.1 (5)	N2—C16—C17—S1	−8.3 (7)
O1—C8—C9—C10	−178.3 (4)	C20—S1—C17—C18	0.2 (4)
C13—C8—C9—C10	2.3 (7)	C20—S1—C17—C16	−178.8 (4)
C8—C9—C10—C11	−0.2 (7)	C16—C17—C18—C19	179.2 (4)
C9—C10—C11—C12	−1.4 (7)	S1—C17—C18—C19	0.1 (5)
C9—C10—C11—C15	177.3 (4)	C17—C18—C19—C20	−0.5 (6)
C10—C11—C12—C13	0.9 (7)	C18—C19—C20—S1	0.6 (6)
C15—C11—C12—C13	−177.8 (4)	C17—S1—C20—C19	−0.5 (4)
C14—O2—C13—C12	−4.7 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3^i	0.86	1.95	2.811 (5)	175

Symmetry code: (i) −x+2, −y+3, −z.