In the title compound, C
20H
17ClN
2O
4, 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
CCDC reference: 651473
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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
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
C20H17ClN2O4 | F(000) = 800 |
Mr = 384.81 | Dx = 1.391 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 1668 reflections |
a = 7.797 (2) Å | θ = 2.9–20.2° |
b = 17.456 (4) Å | µ = 0.24 mm−1 |
c = 13.500 (3) Å | T = 294 K |
V = 1837.4 (8) Å3 | Block, colourless |
Z = 4 | 0.20 × 0.18 × 0.18 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2838 independent reflections |
Radiation source: fine-focus sealed tube | 1743 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→7 |
Tmin = 0.923, Tmax = 0.958 | k = −20→19 |
7263 measured reflections | l = −13→16 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.046 | H-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 reflections | Δρmax = 0.18 e Å−3 |
246 parameters | Δρmin = −0.17 e Å−3 |
7 restraints | Absolute structure: Flack (1983), with 1134 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.6842 (2) | 0.48526 (10) | 1.34550 (12) | 0.1095 (6) | |
O1 | 0.7267 (3) | 0.40745 (14) | 0.87244 (18) | 0.0559 (7) | |
O2 | 0.6436 (4) | 0.27130 (15) | 0.8220 (2) | 0.0705 (9) | |
O3 | 0.6572 (3) | 0.15143 (16) | 0.3146 (2) | 0.0629 (8) | |
O4 | 0.9870 (4) | 0.22846 (18) | 0.1624 (2) | 0.0740 (9) | |
N1 | 0.7978 (4) | 0.2547 (2) | 0.4438 (2) | 0.0549 (9) | |
N2 | 0.8591 (4) | 0.2419 (2) | 0.3490 (2) | 0.0575 (9) | |
H2 | 0.9457 | 0.2675 | 0.3274 | 0.069* | |
C1 | 0.6632 (6) | 0.5382 (3) | 1.0597 (3) | 0.0640 (12) | |
H1 | 0.6123 | 0.5757 | 1.0206 | 0.077* | |
C2 | 0.6388 (6) | 0.5392 (3) | 1.1599 (4) | 0.0722 (14) | |
H2A | 0.5714 | 0.5772 | 1.1886 | 0.087* | |
C3 | 0.7138 (6) | 0.4844 (3) | 1.2181 (3) | 0.0684 (14) | |
C4 | 0.8135 (6) | 0.4284 (3) | 1.1777 (3) | 0.0673 (13) | |
H4 | 0.8648 | 0.3914 | 1.2174 | 0.081* | |
C5 | 0.8367 (6) | 0.4279 (2) | 1.0759 (3) | 0.0655 (13) | |
H5 | 0.9040 | 0.3900 | 1.0472 | 0.079* | |
C6 | 0.7618 (5) | 0.4827 (2) | 1.0161 (3) | 0.0533 (11) | |
C7 | 0.7871 (6) | 0.4801 (2) | 0.9068 (3) | 0.0636 (12) | |
H7A | 0.7234 | 0.5212 | 0.8753 | 0.076* | |
H7B | 0.9076 | 0.4862 | 0.8909 | 0.076* | |
C8 | 0.7572 (5) | 0.3894 (2) | 0.7759 (3) | 0.0456 (9) | |
C9 | 0.8276 (5) | 0.4376 (2) | 0.7078 (3) | 0.0544 (11) | |
H9 | 0.8529 | 0.4879 | 0.7252 | 0.065* | |
C10 | 0.8616 (5) | 0.4121 (2) | 0.6130 (3) | 0.0590 (11) | |
H10 | 0.9148 | 0.4448 | 0.5681 | 0.071* | |
C11 | 0.8180 (5) | 0.3389 (2) | 0.5837 (3) | 0.0524 (10) | |
C12 | 0.7422 (5) | 0.2900 (2) | 0.6540 (3) | 0.0530 (10) | |
H12 | 0.7117 | 0.2404 | 0.6359 | 0.064* | |
C13 | 0.7127 (5) | 0.3148 (2) | 0.7487 (3) | 0.0490 (11) | |
C14 | 0.6537 (6) | 0.1916 (2) | 0.8124 (3) | 0.0698 (13) | |
H14A | 0.7712 | 0.1767 | 0.8036 | 0.105* | |
H14B | 0.5879 | 0.1755 | 0.7560 | 0.105* | |
H14C | 0.6088 | 0.1678 | 0.8710 | 0.105* | |
C15 | 0.8604 (5) | 0.3144 (3) | 0.4838 (3) | 0.0593 (11) | |
H15 | 0.9372 | 0.3439 | 0.4473 | 0.071* | |
C16 | 0.7831 (6) | 0.1893 (2) | 0.2902 (3) | 0.0516 (10) | |
C17 | 0.8590 (5) | 0.1808 (2) | 0.1915 (3) | 0.0489 (10) | |
C18 | 0.8186 (6) | 0.1324 (2) | 0.1178 (3) | 0.0638 (12) | |
H18 | 0.7365 | 0.0938 | 0.1186 | 0.077* | |
C19 | 0.9294 (7) | 0.1531 (3) | 0.0374 (3) | 0.0710 (13) | |
H19 | 0.9321 | 0.1305 | −0.0250 | 0.085* | |
C20 | 1.0258 (7) | 0.2094 (3) | 0.0677 (3) | 0.0801 (14) | |
H20 | 1.1097 | 0.2332 | 0.0296 | 0.096* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.1281 (12) | 0.1411 (14) | 0.0592 (8) | −0.0024 (10) | 0.0138 (8) | −0.0150 (8) |
O1 | 0.0719 (19) | 0.0500 (16) | 0.0457 (17) | −0.0131 (14) | 0.0162 (13) | −0.0078 (12) |
O2 | 0.112 (3) | 0.0476 (16) | 0.0517 (17) | −0.0175 (15) | 0.0326 (16) | −0.0051 (13) |
O3 | 0.0641 (19) | 0.0663 (18) | 0.0583 (17) | −0.0088 (15) | 0.0171 (15) | 0.0026 (15) |
O4 | 0.082 (2) | 0.084 (2) | 0.0557 (18) | −0.0123 (18) | 0.0264 (17) | −0.0066 (16) |
N1 | 0.058 (2) | 0.068 (2) | 0.0390 (19) | 0.0008 (18) | 0.0146 (16) | −0.0016 (18) |
N2 | 0.061 (2) | 0.072 (2) | 0.0403 (18) | −0.0104 (18) | 0.0136 (18) | −0.0014 (18) |
C1 | 0.071 (3) | 0.057 (3) | 0.065 (3) | 0.006 (2) | −0.005 (2) | −0.009 (2) |
C2 | 0.065 (3) | 0.077 (4) | 0.074 (4) | 0.009 (2) | 0.004 (3) | −0.021 (3) |
C3 | 0.064 (3) | 0.085 (4) | 0.056 (3) | −0.010 (3) | 0.003 (2) | −0.020 (3) |
C4 | 0.082 (4) | 0.065 (3) | 0.055 (3) | 0.001 (3) | −0.005 (3) | −0.005 (2) |
C5 | 0.068 (3) | 0.057 (3) | 0.072 (3) | 0.009 (2) | 0.006 (2) | −0.013 (2) |
C6 | 0.054 (3) | 0.049 (3) | 0.057 (3) | −0.010 (2) | 0.005 (2) | −0.011 (2) |
C7 | 0.080 (3) | 0.051 (3) | 0.060 (3) | −0.015 (2) | 0.006 (2) | −0.006 (2) |
C8 | 0.048 (3) | 0.048 (2) | 0.041 (2) | 0.0017 (17) | 0.0082 (18) | 0.002 (2) |
C9 | 0.062 (3) | 0.051 (2) | 0.050 (3) | −0.006 (2) | 0.008 (2) | 0.001 (2) |
C10 | 0.065 (3) | 0.063 (3) | 0.048 (2) | −0.010 (2) | 0.013 (2) | 0.007 (2) |
C11 | 0.051 (3) | 0.064 (3) | 0.042 (2) | −0.001 (2) | 0.011 (2) | −0.005 (2) |
C12 | 0.059 (3) | 0.053 (2) | 0.047 (3) | −0.006 (2) | 0.010 (2) | −0.006 (2) |
C13 | 0.052 (3) | 0.049 (2) | 0.046 (3) | −0.004 (2) | 0.0130 (18) | 0.0034 (19) |
C14 | 0.093 (3) | 0.055 (3) | 0.062 (3) | −0.017 (2) | 0.006 (2) | 0.003 (2) |
C15 | 0.064 (3) | 0.069 (3) | 0.044 (2) | −0.007 (2) | 0.020 (2) | 0.000 (2) |
C16 | 0.056 (3) | 0.055 (3) | 0.044 (2) | 0.010 (2) | 0.009 (2) | 0.005 (2) |
C17 | 0.049 (2) | 0.050 (3) | 0.048 (2) | 0.003 (2) | 0.0110 (19) | 0.0059 (19) |
C18 | 0.065 (3) | 0.054 (3) | 0.072 (3) | 0.001 (2) | −0.005 (2) | −0.013 (3) |
C19 | 0.086 (4) | 0.080 (3) | 0.047 (3) | 0.023 (3) | −0.001 (3) | −0.014 (2) |
C20 | 0.098 (4) | 0.093 (4) | 0.049 (3) | 0.009 (3) | 0.030 (3) | 0.000 (3) |
Geometric parameters (Å, º) top
Cl1—C3 | 1.735 (5) | C7—H7A | 0.9700 |
O1—C8 | 1.362 (4) | C7—H7B | 0.9700 |
O1—C7 | 1.430 (5) | C8—C9 | 1.362 (5) |
O2—C13 | 1.359 (4) | C8—C13 | 1.397 (5) |
O2—C14 | 1.400 (5) | C9—C10 | 1.380 (5) |
O3—C16 | 1.228 (4) | C9—H9 | 0.9300 |
O4—C20 | 1.356 (5) | C10—C11 | 1.380 (6) |
O4—C17 | 1.358 (4) | C10—H10 | 0.9300 |
N1—C15 | 1.271 (5) | C11—C12 | 1.406 (5) |
N1—N2 | 1.385 (4) | C11—C15 | 1.453 (5) |
N2—C16 | 1.351 (5) | C12—C13 | 1.369 (5) |
N2—H2 | 0.8600 | C12—H12 | 0.9300 |
C1—C6 | 1.370 (6) | C14—H14A | 0.9600 |
C1—C2 | 1.366 (6) | C14—H14B | 0.9600 |
C1—H1 | 0.9300 | C14—H14C | 0.9600 |
C2—C3 | 1.370 (7) | C15—H15 | 0.9300 |
C2—H2A | 0.9300 | C16—C17 | 1.466 (5) |
C3—C4 | 1.363 (6) | C17—C18 | 1.342 (5) |
C4—C5 | 1.386 (6) | C18—C19 | 1.433 (6) |
C4—H4 | 0.9300 | C18—H18 | 0.9300 |
C5—C6 | 1.380 (6) | C19—C20 | 1.303 (7) |
C5—H5 | 0.9300 | C19—H19 | 0.9300 |
C6—C7 | 1.490 (6) | C20—H20 | 0.9300 |
| | | |
C8—O1—C7 | 117.3 (3) | C11—C10—C9 | 121.1 (4) |
C13—O2—C14 | 117.8 (3) | C11—C10—H10 | 119.5 |
C20—O4—C17 | 106.6 (4) | C9—C10—H10 | 119.5 |
C15—N1—N2 | 113.1 (3) | C10—C11—C12 | 118.2 (4) |
C16—N2—N1 | 120.1 (3) | C10—C11—C15 | 118.8 (4) |
C16—N2—H2 | 120.0 | C12—C11—C15 | 123.0 (4) |
N1—N2—H2 | 120.0 | C13—C12—C11 | 120.6 (4) |
C6—C1—C2 | 120.8 (5) | C13—C12—H12 | 119.7 |
C6—C1—H1 | 119.6 | C11—C12—H12 | 119.7 |
C2—C1—H1 | 119.6 | O2—C13—C12 | 124.8 (3) |
C3—C2—C1 | 120.0 (4) | O2—C13—C8 | 115.3 (3) |
C3—C2—H2A | 120.0 | C12—C13—C8 | 119.9 (4) |
C1—C2—H2A | 120.0 | O2—C14—H14A | 109.5 |
C4—C3—C2 | 121.0 (4) | O2—C14—H14B | 109.5 |
C4—C3—Cl1 | 118.7 (4) | H14A—C14—H14B | 109.5 |
C2—C3—Cl1 | 120.4 (4) | O2—C14—H14C | 109.5 |
C3—C4—C5 | 118.4 (5) | H14A—C14—H14C | 109.5 |
C3—C4—H4 | 120.8 | H14B—C14—H14C | 109.5 |
C5—C4—H4 | 120.8 | N1—C15—C11 | 123.2 (4) |
C6—C5—C4 | 121.3 (4) | N1—C15—H15 | 118.4 |
C6—C5—H5 | 119.3 | C11—C15—H15 | 118.4 |
C4—C5—H5 | 119.3 | O3—C16—N2 | 124.0 (4) |
C1—C6—C5 | 118.5 (4) | O3—C16—C17 | 120.7 (4) |
C1—C6—C7 | 121.4 (4) | N2—C16—C17 | 115.2 (4) |
C5—C6—C7 | 120.1 (4) | C18—C17—O4 | 110.1 (3) |
O1—C7—C6 | 107.8 (3) | C18—C17—C16 | 130.1 (4) |
O1—C7—H7A | 110.2 | O4—C17—C16 | 119.8 (4) |
C6—C7—H7A | 110.2 | C17—C18—C19 | 105.2 (4) |
O1—C7—H7B | 110.2 | C17—C18—H18 | 127.4 |
C6—C7—H7B | 110.2 | C19—C18—H18 | 127.4 |
H7A—C7—H7B | 108.5 | C20—C19—C18 | 107.4 (4) |
O1—C8—C9 | 125.0 (4) | C20—C19—H19 | 126.3 |
O1—C8—C13 | 115.1 (3) | C18—C19—H19 | 126.3 |
C9—C8—C13 | 119.9 (4) | C19—C20—O4 | 110.7 (4) |
C8—C9—C10 | 120.3 (4) | C19—C20—H20 | 124.7 |
C8—C9—H9 | 119.9 | O4—C20—H20 | 124.7 |
C10—C9—H9 | 119.9 | | |
| | | |
C15—N1—N2—C16 | −168.1 (4) | C14—O2—C13—C8 | −157.3 (3) |
C6—C1—C2—C3 | 0.2 (8) | C11—C12—C13—O2 | −178.6 (4) |
C1—C2—C3—C4 | 0.2 (8) | C11—C12—C13—C8 | 0.4 (6) |
C1—C2—C3—Cl1 | 179.8 (4) | O1—C8—C13—O2 | 0.8 (5) |
C2—C3—C4—C5 | −0.4 (7) | C9—C8—C13—O2 | 179.9 (4) |
Cl1—C3—C4—C5 | 180.0 (3) | O1—C8—C13—C12 | −178.3 (3) |
C3—C4—C5—C6 | 0.3 (7) | C9—C8—C13—C12 | 0.9 (6) |
C2—C1—C6—C5 | −0.3 (7) | N2—N1—C15—C11 | −178.8 (3) |
C2—C1—C6—C7 | 178.9 (4) | C10—C11—C15—N1 | −166.0 (4) |
C4—C5—C6—C1 | 0.1 (6) | C12—C11—C15—N1 | 17.4 (6) |
C4—C5—C6—C7 | −179.2 (4) | N1—N2—C16—O3 | 1.4 (6) |
C8—O1—C7—C6 | −172.2 (3) | N1—N2—C16—C17 | 180.0 (3) |
C1—C6—C7—O1 | −121.4 (4) | C20—O4—C17—C18 | 0.5 (5) |
C5—C6—C7—O1 | 57.8 (5) | C20—O4—C17—C16 | −177.4 (4) |
C7—O1—C8—C9 | −5.8 (6) | O3—C16—C17—C18 | −4.1 (7) |
C7—O1—C8—C13 | 173.3 (4) | N2—C16—C17—C18 | 177.3 (4) |
O1—C8—C9—C10 | 176.5 (4) | O3—C16—C17—O4 | 173.4 (3) |
C13—C8—C9—C10 | −2.6 (6) | N2—C16—C17—O4 | −5.2 (5) |
C8—C9—C10—C11 | 3.1 (7) | O4—C17—C18—C19 | −0.8 (5) |
C9—C10—C11—C12 | −1.8 (6) | C16—C17—C18—C19 | 176.9 (4) |
C9—C10—C11—C15 | −178.6 (4) | C17—C18—C19—C20 | 0.8 (5) |
C10—C11—C12—C13 | 0.0 (6) | C18—C19—C20—O4 | −0.5 (6) |
C15—C11—C12—C13 | 176.7 (4) | C17—O4—C20—C19 | 0.0 (5) |
C14—O2—C13—C12 | 21.7 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3i | 0.86 | 2.18 | 3.014 (4) | 163 |
C15—H15···O3i | 0.93 | 2.48 | 3.306 (5) | 148 |
Symmetry code: (i) x+1/2, −y+1/2, z. |