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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046095/is2098sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046095/is2098Isup2.hkl
Contains datablock I

CCDC reference: 630023

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

Computing details top

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 top
Crystal data top
C20H17ClN2O3SZ = 2
Mr = 400.88F(000) = 416
Triclinic, P1Dx = 1.424 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.275 (3) ÅCell parameters from 2127 reflections
b = 9.884 (3) Åθ = 2.5–24.6°
c = 11.584 (3) ŵ = 0.34 mm1
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) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3264 independent reflections
Radiation source: fine-focus sealed tube1803 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 98
Tmin = 0.931, Tmax = 0.973k = 119
4778 measured reflectionsl = 1311
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0663P)2 + 0.5087P]
where P = (Fo2 + 2Fc2)/3
3264 reflections(Δ/σ)max < 0.001
246 parametersΔρmax = 0.39 e Å3
6 restraintsΔρmin = 0.39 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
S11.32387 (16)1.21499 (12)0.22251 (12)0.0502 (4)
Cl10.6607 (3)0.06608 (18)0.57963 (17)0.1240 (9)
O10.7948 (4)0.6408 (3)0.2918 (3)0.0476 (9)
O20.5900 (4)0.7551 (3)0.1665 (3)0.0477 (9)
O31.1892 (4)1.5373 (3)0.0465 (3)0.0566 (10)
N11.0441 (4)1.2169 (3)0.1153 (3)0.0383 (9)
N21.0575 (4)1.3453 (3)0.0697 (3)0.0432 (10)
H20.98451.37810.03040.052*
C10.7016 (7)0.4593 (5)0.5230 (5)0.0573 (14)
H10.65190.53990.55520.069*
C20.6489 (7)0.3381 (6)0.5694 (5)0.0622 (15)
H2A0.56320.33600.63160.075*
C30.7246 (8)0.2214 (5)0.5226 (5)0.0592 (15)
C40.8501 (8)0.2227 (5)0.4313 (5)0.0647 (16)
H40.90060.14190.40030.078*
C50.9007 (6)0.3439 (5)0.3858 (4)0.0555 (14)
H50.98710.34530.32400.067*
C60.8261 (6)0.4638 (5)0.4299 (4)0.0457 (12)
C70.8864 (8)0.5959 (5)0.3807 (5)0.0770 (19)
H7A0.87450.66320.44230.092*
H7B1.00160.58460.34820.092*
C80.8346 (6)0.7647 (4)0.2430 (4)0.0405 (11)
C90.9754 (6)0.8273 (5)0.2552 (4)0.0523 (13)
H91.05120.78440.29660.063*
C101.0055 (6)0.9530 (4)0.2064 (4)0.0463 (12)
H101.10120.99410.21560.056*
C110.8952 (5)1.0187 (4)0.1441 (4)0.0362 (10)
C120.7538 (5)0.9526 (4)0.1296 (4)0.0386 (11)
H120.67910.99490.08700.046*
C130.7228 (5)0.8264 (4)0.1771 (4)0.0364 (11)
C140.4664 (6)0.8191 (5)0.1089 (4)0.0519 (13)
H14A0.43090.90450.14560.078*
H14B0.37500.76220.11400.078*
H14C0.50990.83360.02830.078*
C150.9201 (5)1.1545 (4)0.0957 (4)0.0373 (11)
H150.84641.19490.05120.045*
C161.1833 (5)1.4211 (4)0.0855 (4)0.0420 (11)
C171.3156 (5)1.3663 (4)0.1475 (4)0.0387 (11)
C181.4525 (6)1.4355 (5)0.1535 (4)0.0465 (12)
H181.47071.51960.11850.056*
C191.5625 (6)1.3682 (5)0.2171 (4)0.0552 (14)
H191.66171.40180.22870.066*
C201.5080 (6)1.2482 (5)0.2600 (4)0.0551 (14)
H201.56511.19040.30510.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0477 (8)0.0395 (7)0.0668 (9)0.0068 (5)0.0190 (6)0.0183 (6)
Cl10.198 (2)0.0748 (11)0.1198 (16)0.0761 (13)0.0692 (15)0.0521 (11)
O10.051 (2)0.0386 (17)0.061 (2)0.0157 (15)0.0294 (16)0.0230 (15)
O20.044 (2)0.0375 (17)0.068 (2)0.0165 (14)0.0271 (17)0.0191 (16)
O30.055 (2)0.0323 (17)0.089 (3)0.0152 (15)0.0265 (19)0.0251 (17)
N10.040 (2)0.0273 (19)0.048 (2)0.0081 (16)0.0095 (18)0.0094 (17)
N20.042 (2)0.0308 (19)0.061 (3)0.0109 (17)0.0193 (19)0.0173 (18)
C10.060 (4)0.048 (3)0.065 (4)0.004 (3)0.018 (3)0.006 (3)
C20.054 (4)0.079 (4)0.053 (4)0.015 (3)0.003 (3)0.014 (3)
C30.087 (4)0.047 (3)0.053 (3)0.026 (3)0.033 (3)0.020 (3)
C40.092 (5)0.047 (3)0.059 (4)0.009 (3)0.028 (3)0.005 (3)
C50.055 (3)0.070 (4)0.041 (3)0.002 (3)0.004 (2)0.007 (3)
C60.051 (3)0.051 (3)0.041 (3)0.013 (2)0.022 (2)0.017 (2)
C70.095 (5)0.067 (4)0.086 (4)0.034 (3)0.061 (4)0.046 (3)
C80.046 (3)0.032 (2)0.048 (3)0.011 (2)0.018 (2)0.011 (2)
C90.049 (3)0.043 (3)0.072 (4)0.011 (2)0.031 (3)0.020 (3)
C100.042 (3)0.036 (2)0.068 (3)0.012 (2)0.025 (2)0.012 (2)
C110.041 (3)0.029 (2)0.038 (3)0.0081 (19)0.007 (2)0.0034 (19)
C120.039 (3)0.033 (2)0.046 (3)0.0025 (19)0.013 (2)0.006 (2)
C130.035 (3)0.034 (2)0.043 (3)0.0094 (19)0.011 (2)0.009 (2)
C140.042 (3)0.044 (3)0.075 (4)0.009 (2)0.027 (3)0.011 (3)
C150.041 (3)0.032 (2)0.041 (3)0.006 (2)0.010 (2)0.005 (2)
C160.039 (3)0.035 (3)0.053 (3)0.006 (2)0.011 (2)0.010 (2)
C170.040 (3)0.034 (2)0.044 (3)0.008 (2)0.009 (2)0.007 (2)
C180.047 (3)0.040 (3)0.054 (3)0.011 (2)0.011 (2)0.003 (2)
C190.043 (3)0.060 (3)0.068 (4)0.010 (3)0.022 (3)0.001 (3)
C200.048 (3)0.058 (3)0.064 (4)0.001 (2)0.025 (3)0.005 (3)
Geometric parameters (Å, º) top
S1—C201.697 (5)C7—H7A0.9700
S1—C171.727 (4)C7—H7B0.9700
Cl1—C31.741 (5)C8—C91.375 (6)
O1—C81.379 (5)C8—C131.400 (6)
O1—C71.425 (5)C9—C101.379 (6)
O2—C131.359 (5)C9—H90.9300
O2—C141.424 (5)C10—C111.382 (6)
O3—C161.232 (5)C10—H100.9300
N1—C151.275 (5)C11—C121.403 (6)
N1—N21.374 (4)C11—C151.463 (5)
N2—C161.350 (5)C12—C131.379 (5)
N2—H20.8600C12—H120.9300
C1—C61.373 (7)C14—H14A0.9600
C1—C21.373 (7)C14—H14B0.9600
C1—H10.9300C14—H14C0.9600
C2—C31.359 (8)C15—H150.9300
C2—H2A0.9300C16—C171.476 (6)
C3—C41.363 (8)C17—C181.365 (6)
C4—C51.365 (7)C18—C191.397 (6)
C4—H40.9300C18—H180.9300
C5—C61.372 (7)C19—C201.354 (6)
C5—H50.9300C19—H190.9300
C6—C71.499 (6)C20—H200.9300
C20—S1—C1791.5 (2)C9—C10—C11120.9 (4)
C8—O1—C7115.2 (3)C9—C10—H10119.6
C13—O2—C14117.7 (3)C11—C10—H10119.6
C15—N1—N2116.0 (4)C10—C11—C12118.1 (4)
C16—N2—N1121.2 (4)C10—C11—C15122.2 (4)
C16—N2—H2119.4C12—C11—C15119.7 (4)
N1—N2—H2119.4C13—C12—C11121.6 (4)
C6—C1—C2121.3 (5)C13—C12—H12119.2
C6—C1—H1119.4C11—C12—H12119.2
C2—C1—H1119.4O2—C13—C12125.4 (4)
C3—C2—C1118.6 (5)O2—C13—C8115.9 (4)
C3—C2—H2A120.7C12—C13—C8118.7 (4)
C1—C2—H2A120.7O2—C14—H14A109.5
C2—C3—C4121.4 (5)O2—C14—H14B109.5
C2—C3—Cl1119.7 (5)H14A—C14—H14B109.5
C4—C3—Cl1118.9 (5)O2—C14—H14C109.5
C3—C4—C5119.3 (5)H14A—C14—H14C109.5
C3—C4—H4120.4H14B—C14—H14C109.5
C5—C4—H4120.4N1—C15—C11119.2 (4)
C4—C5—C6120.9 (5)N1—C15—H15120.4
C4—C5—H5119.5C11—C15—H15120.4
C6—C5—H5119.5O3—C16—N2119.6 (4)
C5—C6—C1118.4 (5)O3—C16—C17119.3 (4)
C5—C6—C7120.1 (5)N2—C16—C17121.1 (4)
C1—C6—C7121.4 (5)C18—C17—C16122.0 (4)
O1—C7—C6109.7 (4)C18—C17—S1110.2 (3)
O1—C7—H7A109.7C16—C17—S1127.8 (3)
C6—C7—H7A109.7C17—C18—C19113.6 (4)
O1—C7—H7B109.7C17—C18—H18123.2
C6—C7—H7B109.7C19—C18—H18123.2
H7A—C7—H7B108.2C20—C19—C18112.1 (4)
C9—C8—O1123.7 (4)C20—C19—H19124.0
C9—C8—C13120.0 (4)C18—C19—H19124.0
O1—C8—C13116.3 (4)C19—C20—S1112.5 (4)
C8—C9—C10120.6 (4)C19—C20—H20123.7
C8—C9—H9119.7S1—C20—H20123.7
C10—C9—H9119.7
C15—N1—N2—C16179.6 (4)C14—O2—C13—C8174.7 (4)
C6—C1—C2—C31.1 (8)C11—C12—C13—O2179.5 (4)
C1—C2—C3—C40.2 (8)C11—C12—C13—C81.2 (7)
C1—C2—C3—Cl1180.0 (4)C9—C8—C13—O2177.8 (4)
C2—C3—C4—C50.0 (8)O1—C8—C13—O21.7 (6)
Cl1—C3—C4—C5179.8 (4)C9—C8—C13—C122.7 (7)
C3—C4—C5—C60.7 (8)O1—C8—C13—C12177.8 (4)
C4—C5—C6—C11.6 (7)N2—N1—C15—C11178.4 (4)
C4—C5—C6—C7178.4 (4)C10—C11—C15—N12.8 (7)
C2—C1—C6—C51.8 (7)C12—C11—C15—N1175.9 (4)
C2—C1—C6—C7178.6 (5)N1—N2—C16—O3177.8 (4)
C8—O1—C7—C6177.4 (4)N1—N2—C16—C173.0 (7)
C5—C6—C7—O193.8 (6)O3—C16—C17—C186.4 (7)
C1—C6—C7—O189.4 (6)N2—C16—C17—C18172.8 (4)
C7—O1—C8—C915.4 (7)O3—C16—C17—S1172.5 (4)
C7—O1—C8—C13165.1 (5)N2—C16—C17—S18.3 (7)
O1—C8—C9—C10178.3 (4)C20—S1—C17—C180.2 (4)
C13—C8—C9—C102.3 (7)C20—S1—C17—C16178.8 (4)
C8—C9—C10—C110.2 (7)C16—C17—C18—C19179.2 (4)
C9—C10—C11—C121.4 (7)S1—C17—C18—C190.1 (5)
C9—C10—C11—C15177.3 (4)C17—C18—C19—C200.5 (6)
C10—C11—C12—C130.9 (7)C18—C19—C20—S10.6 (6)
C15—C11—C12—C13177.8 (4)C17—S1—C20—C190.5 (4)
C14—O2—C13—C124.7 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.861.952.811 (5)175
Symmetry code: (i) x+2, y+3, z.
 

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