Download citation
Download citation
link to html
In the title compound, C20H17ClN2O4, the vanillin group makes dihedral angles of 54.50 (10) and 23.85 (15)° with the chloro­benzene ring and the furan mean plane, respectively. Packing is stabilized by inter­molecular N—H...O hydrogen bonds and weak non-classical inter­molecular C—H...O hydrogen-bonding inter­actions that link adjacent mol­ecules into one-dimensional extended chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043807/at2139sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043807/at2139Isup2.hkl
Contains datablock I

CCDC reference: 651473

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.046
  • wR factor = 0.117
  • Data-to-parameter ratio = 11.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for O4 - C17 .. 5.12 su PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.02 From the CIF: _reflns_number_total 2838 Count of symmetry unique reflns 1704 Completeness (_total/calc) 166.55% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1134 Fraction of Friedel pairs measured 0.665 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 7
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 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]furan-2-carbohydrazide top
Crystal data top
C20H17ClN2O4F(000) = 800
Mr = 384.81Dx = 1.391 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 1668 reflections
a = 7.797 (2) Åθ = 2.9–20.2°
b = 17.456 (4) ŵ = 0.24 mm1
c = 13.500 (3) ÅT = 294 K
V = 1837.4 (8) Å3Block, colourless
Z = 40.20 × 0.18 × 0.18 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2838 independent reflections
Radiation source: fine-focus sealed tube1743 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 97
Tmin = 0.923, Tmax = 0.958k = 2019
7263 measured reflectionsl = 1316
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.117 w = 1/[σ2(Fo2) + (0.0549P)2 + 0.0942P]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.009
2838 reflectionsΔρmax = 0.18 e Å3
246 parametersΔρmin = 0.17 e Å3
7 restraintsAbsolute structure: Flack (1983), with 1134 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.13 (13)
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
Cl10.6842 (2)0.48526 (10)1.34550 (12)0.1095 (6)
O10.7267 (3)0.40745 (14)0.87244 (18)0.0559 (7)
O20.6436 (4)0.27130 (15)0.8220 (2)0.0705 (9)
O30.6572 (3)0.15143 (16)0.3146 (2)0.0629 (8)
O40.9870 (4)0.22846 (18)0.1624 (2)0.0740 (9)
N10.7978 (4)0.2547 (2)0.4438 (2)0.0549 (9)
N20.8591 (4)0.2419 (2)0.3490 (2)0.0575 (9)
H20.94570.26750.32740.069*
C10.6632 (6)0.5382 (3)1.0597 (3)0.0640 (12)
H10.61230.57571.02060.077*
C20.6388 (6)0.5392 (3)1.1599 (4)0.0722 (14)
H2A0.57140.57721.18860.087*
C30.7138 (6)0.4844 (3)1.2181 (3)0.0684 (14)
C40.8135 (6)0.4284 (3)1.1777 (3)0.0673 (13)
H40.86480.39141.21740.081*
C50.8367 (6)0.4279 (2)1.0759 (3)0.0655 (13)
H50.90400.39001.04720.079*
C60.7618 (5)0.4827 (2)1.0161 (3)0.0533 (11)
C70.7871 (6)0.4801 (2)0.9068 (3)0.0636 (12)
H7A0.72340.52120.87530.076*
H7B0.90760.48620.89090.076*
C80.7572 (5)0.3894 (2)0.7759 (3)0.0456 (9)
C90.8276 (5)0.4376 (2)0.7078 (3)0.0544 (11)
H90.85290.48790.72520.065*
C100.8616 (5)0.4121 (2)0.6130 (3)0.0590 (11)
H100.91480.44480.56810.071*
C110.8180 (5)0.3389 (2)0.5837 (3)0.0524 (10)
C120.7422 (5)0.2900 (2)0.6540 (3)0.0530 (10)
H120.71170.24040.63590.064*
C130.7127 (5)0.3148 (2)0.7487 (3)0.0490 (11)
C140.6537 (6)0.1916 (2)0.8124 (3)0.0698 (13)
H14A0.77120.17670.80360.105*
H14B0.58790.17550.75600.105*
H14C0.60880.16780.87100.105*
C150.8604 (5)0.3144 (3)0.4838 (3)0.0593 (11)
H150.93720.34390.44730.071*
C160.7831 (6)0.1893 (2)0.2902 (3)0.0516 (10)
C170.8590 (5)0.1808 (2)0.1915 (3)0.0489 (10)
C180.8186 (6)0.1324 (2)0.1178 (3)0.0638 (12)
H180.73650.09380.11860.077*
C190.9294 (7)0.1531 (3)0.0374 (3)0.0710 (13)
H190.93210.13050.02500.085*
C201.0258 (7)0.2094 (3)0.0677 (3)0.0801 (14)
H201.10970.23320.02960.096*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.1281 (12)0.1411 (14)0.0592 (8)0.0024 (10)0.0138 (8)0.0150 (8)
O10.0719 (19)0.0500 (16)0.0457 (17)0.0131 (14)0.0162 (13)0.0078 (12)
O20.112 (3)0.0476 (16)0.0517 (17)0.0175 (15)0.0326 (16)0.0051 (13)
O30.0641 (19)0.0663 (18)0.0583 (17)0.0088 (15)0.0171 (15)0.0026 (15)
O40.082 (2)0.084 (2)0.0557 (18)0.0123 (18)0.0264 (17)0.0066 (16)
N10.058 (2)0.068 (2)0.0390 (19)0.0008 (18)0.0146 (16)0.0016 (18)
N20.061 (2)0.072 (2)0.0403 (18)0.0104 (18)0.0136 (18)0.0014 (18)
C10.071 (3)0.057 (3)0.065 (3)0.006 (2)0.005 (2)0.009 (2)
C20.065 (3)0.077 (4)0.074 (4)0.009 (2)0.004 (3)0.021 (3)
C30.064 (3)0.085 (4)0.056 (3)0.010 (3)0.003 (2)0.020 (3)
C40.082 (4)0.065 (3)0.055 (3)0.001 (3)0.005 (3)0.005 (2)
C50.068 (3)0.057 (3)0.072 (3)0.009 (2)0.006 (2)0.013 (2)
C60.054 (3)0.049 (3)0.057 (3)0.010 (2)0.005 (2)0.011 (2)
C70.080 (3)0.051 (3)0.060 (3)0.015 (2)0.006 (2)0.006 (2)
C80.048 (3)0.048 (2)0.041 (2)0.0017 (17)0.0082 (18)0.002 (2)
C90.062 (3)0.051 (2)0.050 (3)0.006 (2)0.008 (2)0.001 (2)
C100.065 (3)0.063 (3)0.048 (2)0.010 (2)0.013 (2)0.007 (2)
C110.051 (3)0.064 (3)0.042 (2)0.001 (2)0.011 (2)0.005 (2)
C120.059 (3)0.053 (2)0.047 (3)0.006 (2)0.010 (2)0.006 (2)
C130.052 (3)0.049 (2)0.046 (3)0.004 (2)0.0130 (18)0.0034 (19)
C140.093 (3)0.055 (3)0.062 (3)0.017 (2)0.006 (2)0.003 (2)
C150.064 (3)0.069 (3)0.044 (2)0.007 (2)0.020 (2)0.000 (2)
C160.056 (3)0.055 (3)0.044 (2)0.010 (2)0.009 (2)0.005 (2)
C170.049 (2)0.050 (3)0.048 (2)0.003 (2)0.0110 (19)0.0059 (19)
C180.065 (3)0.054 (3)0.072 (3)0.001 (2)0.005 (2)0.013 (3)
C190.086 (4)0.080 (3)0.047 (3)0.023 (3)0.001 (3)0.014 (2)
C200.098 (4)0.093 (4)0.049 (3)0.009 (3)0.030 (3)0.000 (3)
Geometric parameters (Å, º) top
Cl1—C31.735 (5)C7—H7A0.9700
O1—C81.362 (4)C7—H7B0.9700
O1—C71.430 (5)C8—C91.362 (5)
O2—C131.359 (4)C8—C131.397 (5)
O2—C141.400 (5)C9—C101.380 (5)
O3—C161.228 (4)C9—H90.9300
O4—C201.356 (5)C10—C111.380 (6)
O4—C171.358 (4)C10—H100.9300
N1—C151.271 (5)C11—C121.406 (5)
N1—N21.385 (4)C11—C151.453 (5)
N2—C161.351 (5)C12—C131.369 (5)
N2—H20.8600C12—H120.9300
C1—C61.370 (6)C14—H14A0.9600
C1—C21.366 (6)C14—H14B0.9600
C1—H10.9300C14—H14C0.9600
C2—C31.370 (7)C15—H150.9300
C2—H2A0.9300C16—C171.466 (5)
C3—C41.363 (6)C17—C181.342 (5)
C4—C51.386 (6)C18—C191.433 (6)
C4—H40.9300C18—H180.9300
C5—C61.380 (6)C19—C201.303 (7)
C5—H50.9300C19—H190.9300
C6—C71.490 (6)C20—H200.9300
C8—O1—C7117.3 (3)C11—C10—C9121.1 (4)
C13—O2—C14117.8 (3)C11—C10—H10119.5
C20—O4—C17106.6 (4)C9—C10—H10119.5
C15—N1—N2113.1 (3)C10—C11—C12118.2 (4)
C16—N2—N1120.1 (3)C10—C11—C15118.8 (4)
C16—N2—H2120.0C12—C11—C15123.0 (4)
N1—N2—H2120.0C13—C12—C11120.6 (4)
C6—C1—C2120.8 (5)C13—C12—H12119.7
C6—C1—H1119.6C11—C12—H12119.7
C2—C1—H1119.6O2—C13—C12124.8 (3)
C3—C2—C1120.0 (4)O2—C13—C8115.3 (3)
C3—C2—H2A120.0C12—C13—C8119.9 (4)
C1—C2—H2A120.0O2—C14—H14A109.5
C4—C3—C2121.0 (4)O2—C14—H14B109.5
C4—C3—Cl1118.7 (4)H14A—C14—H14B109.5
C2—C3—Cl1120.4 (4)O2—C14—H14C109.5
C3—C4—C5118.4 (5)H14A—C14—H14C109.5
C3—C4—H4120.8H14B—C14—H14C109.5
C5—C4—H4120.8N1—C15—C11123.2 (4)
C6—C5—C4121.3 (4)N1—C15—H15118.4
C6—C5—H5119.3C11—C15—H15118.4
C4—C5—H5119.3O3—C16—N2124.0 (4)
C1—C6—C5118.5 (4)O3—C16—C17120.7 (4)
C1—C6—C7121.4 (4)N2—C16—C17115.2 (4)
C5—C6—C7120.1 (4)C18—C17—O4110.1 (3)
O1—C7—C6107.8 (3)C18—C17—C16130.1 (4)
O1—C7—H7A110.2O4—C17—C16119.8 (4)
C6—C7—H7A110.2C17—C18—C19105.2 (4)
O1—C7—H7B110.2C17—C18—H18127.4
C6—C7—H7B110.2C19—C18—H18127.4
H7A—C7—H7B108.5C20—C19—C18107.4 (4)
O1—C8—C9125.0 (4)C20—C19—H19126.3
O1—C8—C13115.1 (3)C18—C19—H19126.3
C9—C8—C13119.9 (4)C19—C20—O4110.7 (4)
C8—C9—C10120.3 (4)C19—C20—H20124.7
C8—C9—H9119.9O4—C20—H20124.7
C10—C9—H9119.9
C15—N1—N2—C16168.1 (4)C14—O2—C13—C8157.3 (3)
C6—C1—C2—C30.2 (8)C11—C12—C13—O2178.6 (4)
C1—C2—C3—C40.2 (8)C11—C12—C13—C80.4 (6)
C1—C2—C3—Cl1179.8 (4)O1—C8—C13—O20.8 (5)
C2—C3—C4—C50.4 (7)C9—C8—C13—O2179.9 (4)
Cl1—C3—C4—C5180.0 (3)O1—C8—C13—C12178.3 (3)
C3—C4—C5—C60.3 (7)C9—C8—C13—C120.9 (6)
C2—C1—C6—C50.3 (7)N2—N1—C15—C11178.8 (3)
C2—C1—C6—C7178.9 (4)C10—C11—C15—N1166.0 (4)
C4—C5—C6—C10.1 (6)C12—C11—C15—N117.4 (6)
C4—C5—C6—C7179.2 (4)N1—N2—C16—O31.4 (6)
C8—O1—C7—C6172.2 (3)N1—N2—C16—C17180.0 (3)
C1—C6—C7—O1121.4 (4)C20—O4—C17—C180.5 (5)
C5—C6—C7—O157.8 (5)C20—O4—C17—C16177.4 (4)
C7—O1—C8—C95.8 (6)O3—C16—C17—C184.1 (7)
C7—O1—C8—C13173.3 (4)N2—C16—C17—C18177.3 (4)
O1—C8—C9—C10176.5 (4)O3—C16—C17—O4173.4 (3)
C13—C8—C9—C102.6 (6)N2—C16—C17—O45.2 (5)
C8—C9—C10—C113.1 (7)O4—C17—C18—C190.8 (5)
C9—C10—C11—C121.8 (6)C16—C17—C18—C19176.9 (4)
C9—C10—C11—C15178.6 (4)C17—C18—C19—C200.8 (5)
C10—C11—C12—C130.0 (6)C18—C19—C20—O40.5 (6)
C15—C11—C12—C13176.7 (4)C17—O4—C20—C190.0 (5)
C14—O2—C13—C1221.7 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O3i0.862.183.014 (4)163
C15—H15···O3i0.932.483.306 (5)148
Symmetry code: (i) x+1/2, y+1/2, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds