organic compounds
Molecules of 5-chlorosalicylaldehyde benzoylhydrazone, C14H11ClN2O2, are linked by an intermolecular amino-carbonyl hydrogen bond into a linear chain that runs along the a axis of the orthorhombic unit cell.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805020775/sj6111sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805020775/sj6111Isup2.hkl |
CCDC reference: 282632
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.002 Å
- R factor = 0.030
- wR factor = 0.085
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.747 0.940 Tmin(prime) and Tmax expected: 0.889 0.940 RR(prime) = 0.840 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.84 PLAT432_ALERT_2_C Short Inter X...Y Contact O1 .. C7 .. 2.97 Ang.
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 27.50 From the CIF: _reflns_number_total 2874 Count of symmetry unique reflns 1529 Completeness (_total/calc) 187.97% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1345 Fraction of Friedel pairs measured 0.880 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 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
Computing details top
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
5-Chlorosalicylaldehyde benzoylhydrazone top
Crystal data top
C14H11ClN2O2 | F(000) = 568 |
Mr = 274.70 | Dx = 1.426 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 11373 reflections |
a = 9.496 (3) Å | θ = 3.0–27.5° |
b = 9.895 (3) Å | µ = 0.30 mm−1 |
c = 13.619 (5) Å | T = 295 K |
V = 1279.6 (7) Å3 | Block, yellow |
Z = 4 | 0.39 × 0.28 × 0.21 mm |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 2874 independent reflections |
Radiation source: fine-focus sealed tube | 2744 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
Detector resolution: 10 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
ω scans | h = −10→12 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −12→12 |
Tmin = 0.747, Tmax = 0.940 | l = −17→17 |
11373 measured reflections |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.030 | w = 1/[σ2(Fo2) + (0.0616P)2 + 0.0336P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.085 | (Δ/σ)max = 0.001 |
S = 1.07 | Δρmax = 0.28 e Å−3 |
2874 reflections | Δρmin = −0.27 e Å−3 |
181 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
3 restraints | Extinction coefficient: 0.045 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1370 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.01 (5) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.74110 (5) | 0.97293 (5) | 0.50000 (4) | 0.0604 (2) | |
O1 | 1.1881 (1) | 0.8246 (2) | 0.2250 (1) | 0.0558 (3) | |
O2 | 1.1560 (1) | 0.6626 (1) | −0.0281 (1) | 0.0498 (3) | |
N1 | 0.9952 (1) | 0.8085 (1) | 0.0913 (1) | 0.0360 (2) | |
N2 | 0.9542 (1) | 0.7788 (1) | −0.0024 (1) | 0.0364 (2) | |
C1 | 0.9455 (1) | 0.8853 (1) | 0.2516 (1) | 0.0358 (3) | |
C2 | 1.0817 (2) | 0.8584 (2) | 0.2859 (1) | 0.0399 (3) | |
C3 | 1.1100 (2) | 0.8645 (2) | 0.3858 (1) | 0.0471 (3) | |
C4 | 1.0061 (2) | 0.8986 (2) | 0.4518 (1) | 0.0469 (3) | |
C5 | 0.8728 (2) | 0.9297 (2) | 0.4172 (1) | 0.0419 (3) | |
C6 | 0.8420 (2) | 0.9245 (2) | 0.3183 (1) | 0.0399 (3) | |
C7 | 0.9063 (2) | 0.8639 (1) | 0.1493 (1) | 0.0363 (3) | |
C8 | 1.0430 (1) | 0.7048 (1) | −0.0590 (1) | 0.0356 (3) | |
C9 | 0.9931 (1) | 0.67565 (1) | −0.1608 (1) | 0.0374 (3) | |
C10 | 1.0477 (2) | 0.5625 (2) | −0.2083 (1) | 0.0457 (3) | |
C11 | 1.0064 (2) | 0.5322 (2) | −0.3034 (2) | 0.0554 (4) | |
C12 | 0.9115 (2) | 0.6128 (2) | −0.3505 (1) | 0.0602 (5) | |
C13 | 0.8567 (2) | 0.7253 (2) | −0.3048 (1) | 0.0649 (5) | |
C14 | 0.8977 (2) | 0.7569 (2) | −0.2097 (1) | 0.0510 (4) | |
H1o | 1.158 (2) | 0.815 (2) | 0.168 (1) | 0.052 (5)* | |
H2n | 0.870 (2) | 0.788 (2) | −0.018 (2) | 0.065 (6)* | |
H3 | 1.2002 | 0.8452 | 0.4084 | 0.057* | |
H4 | 1.0251 | 0.9008 | 0.5187 | 0.056* | |
H6 | 0.7524 | 0.9470 | 0.2962 | 0.048* | |
H7 | 0.8181 | 0.8901 | 0.1266 | 0.044* | |
H10 | 1.1120 | 0.5071 | −0.1762 | 0.055* | |
H11 | 1.0435 | 0.4569 | −0.3350 | 0.066* | |
H12 | 0.8835 | 0.5916 | −0.4141 | 0.072* | |
H13 | 0.7924 | 0.7799 | −0.3376 | 0.078* | |
H14 | 0.8608 | 0.8329 | −0.1788 | 0.061* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0671 (3) | 0.0764 (3) | 0.0376 (2) | 0.0155 (2) | 0.0100 (2) | −0.0059 (1) |
O1 | 0.037 (1) | 0.087 (1) | 0.044 (1) | 0.012 (1) | −0.002 (1) | −0.006 (1) |
O2 | 0.034 (1) | 0.068 (1) | 0.048 (1) | 0.007 (1) | −0.003 (1) | −0.004 (1) |
N1 | 0.034 (1) | 0.043 (1) | 0.031 (1) | −0.003 (1) | −0.001 (1) | −0.000 (1) |
N2 | 0.031 (1) | 0.048 (1) | 0.031 (1) | −0.002 (1) | −0.001 (1) | −0.001 (1) |
C1 | 0.037 (1) | 0.037 (1) | 0.034 (1) | −0.001 (1) | −0.002 (1) | 0.001 (1) |
C2 | 0.037 (1) | 0.042 (1) | 0.041 (1) | 0.003 (1) | −0.002 (1) | −0.002 (1) |
C3 | 0.044 (1) | 0.055 (1) | 0.043 (1) | 0.004 (1) | −0.011 (1) | −0.004 (1) |
C4 | 0.061 (1) | 0.048 (1) | 0.032 (1) | 0.004 (1) | −0.008 (1) | −0.004 (1) |
C5 | 0.049 (1) | 0.042 (1) | 0.034 (1) | 0.002 (1) | 0.003 (1) | −0.004 (1) |
C6 | 0.038 (1) | 0.047 (1) | 0.035 (1) | 0.004 (1) | −0.001 (1) | −0.001 (1) |
C7 | 0.034 (1) | 0.042 (1) | 0.032 (1) | −0.002 (1) | −0.002 (1) | 0.003 (1) |
C8 | 0.031 (1) | 0.041 (1) | 0.034 (1) | −0.004 (1) | 0.001 (1) | 0.000 (1) |
C9 | 0.036 (1) | 0.043 (1) | 0.033 (1) | −0.004 (1) | 0.005 (1) | −0.001 (1) |
C10 | 0.043 (1) | 0.049 (1) | 0.046 (1) | 0.003 (1) | 0.006 (1) | −0.007 (1) |
C11 | 0.058 (1) | 0.062 (1) | 0.046 (1) | −0.009 (1) | 0.014 (1) | −0.017 (1) |
C12 | 0.073 (1) | 0.079 (1) | 0.028 (1) | −0.012 (1) | 0.002 (1) | −0.006 (1) |
C13 | 0.079 (1) | 0.080 (1) | 0.036 (1) | 0.012 (1) | −0.008 (1) | 0.007 (1) |
C14 | 0.063 (1) | 0.055 (1) | 0.036 (1) | 0.011 (1) | −0.001 (1) | 0.001 (1) |
Geometric parameters (Å, º) top
Cl1—C5 | 1.737 (2) | C10—C11 | 1.385 (3) |
O1—C2 | 1.349 (2) | C11—C12 | 1.365 (3) |
O2—C8 | 1.226 (2) | C12—C13 | 1.377 (3) |
N1—C7 | 1.280 (2) | C13—C14 | 1.389 (2) |
N1—N2 | 1.366 (2) | O1—H1o | 0.83 (2) |
N2—C8 | 1.357 (2) | N2—H2n | 0.84 (2) |
C1—C6 | 1.393 (2) | C3—H3 | 0.93 |
C1—C2 | 1.401 (2) | C4—H4 | 0.93 |
C1—C7 | 1.457 (2) | C6—H6 | 0.93 |
C2—C3 | 1.388 (2) | C7—H7 | 0.93 |
C3—C4 | 1.377 (2) | C10—H10 | 0.93 |
C4—C5 | 1.385 (2) | C11—H11 | 0.93 |
C5—C6 | 1.378 (2) | C12—H12 | 0.93 |
C8—C9 | 1.493 (2) | C13—H13 | 0.93 |
C9—C14 | 1.382 (2) | C14—H14 | 0.93 |
C9—C10 | 1.393 (2) | ||
C7—N1—N2 | 118.8 (1) | C12—C13—C14 | 119.9 (2) |
C8—N2—N1 | 118.0 (1) | C9—C14—C13 | 120.1 (2) |
C6—C1—C2 | 119.1 (1) | C2—O1—H1o | 110 (2) |
C6—C1—C7 | 118.9 (1) | C8—N2—H2n | 121 (2) |
C2—C1—C7 | 121.8 (1) | N1—N2—H2n | 119 (2) |
O1—C2—C3 | 117.9 (1) | C4—C3—H3 | 119.6 |
O1—C2—C1 | 122.3 (1) | C2—C3—H3 | 119.6 |
C3—C2—C1 | 119.8 (1) | C3—C4—H4 | 120.4 |
C4—C3—C2 | 120.8 (1) | C5—C4—H4 | 120.4 |
C3—C4—C5 | 119.2 (2) | C5—C6—H6 | 120.1 |
C6—C5—C4 | 121.1 (1) | C1—C6—H6 | 120.1 |
C6—C5—Cl1 | 119.4 (1) | N1—C7—H7 | 120.5 |
C4—C5—Cl1 | 119.4 (1) | C1—C7—H7 | 120.5 |
C5—C6—C1 | 119.9 (1) | C11—C10—H10 | 119.9 |
N1—C7—C1 | 118.9 (1) | C9—C10—H10 | 119.9 |
O2—C8—N2 | 122.1 (1) | C12—C11—H11 | 120.0 |
O2—C8—C9 | 122.1 (1) | C10—C11—H11 | 120.0 |
N2—C8—C9 | 115.7 (1) | C11—C12—H12 | 119.7 |
C14—C9—C10 | 119.2 (2) | C13—C12—H12 | 119.7 |
C14—C9—C8 | 122.9 (1) | C12—C13—H13 | 120.1 |
C10—C9—C8 | 117.9 (1) | C14—C13—H13 | 120.1 |
C11—C10—C9 | 120.2 (2) | C9—C14—H14 | 119.9 |
C12—C11—C10 | 120.0 (2) | C13—C14—H14 | 119.9 |
C11—C12—C13 | 120.6 (2) | ||
C7—N1—N2—C8 | −171.7 (1) | C2—C1—C7—N1 | 6.0 (2) |
C6—C1—C2—O1 | −177.6 (1) | N1—N2—C8—O2 | 1.4 (2) |
C7—C1—C2—O1 | 6.9 (2) | N1—N2—C8—C9 | −179.8 (1) |
C6—C1—C2—C3 | 3.2 (2) | O2—C8—C9—C14 | −155.8 (2) |
C7—C1—C2—C3 | −172.2 (1) | N2—C8—C9—C14 | 25.4 (2) |
O1—C2—C3—C4 | 179.8 (2) | O2—C8—C9—C10 | 23.2 (2) |
C1—C2—C3—C4 | −0.9 (3) | N2—C8—C9—C10 | −155.7 (1) |
C2—C3—C4—C5 | −1.3 (3) | C14—C9—C10—C11 | 0.0 (2) |
C3—C4—C5—C6 | 1.3 (2) | C8—C9—C10—C11 | −179.0 (1) |
C3—C4—C5—Cl1 | 180.0 (1) | C9—C10—C11—C12 | −0.4 (3) |
C4—C5—C6—C1 | 1.0 (2) | C10—C11—C12—C13 | 0.5 (3) |
Cl1—C5—C6—C1 | −177.7 (1) | C11—C12—C13—C14 | −0.3 (3) |
C2—C1—C6—C5 | −3.2 (2) | C10—C9—C14—C13 | 0.3 (3) |
C7—C1—C6—C5 | 172.4 (1) | C8—C9—C14—C13 | 179.2 (2) |
N2—N1—C7—C1 | 174.8 (1) | C12—C13—C14—C9 | −0.1 (3) |
C6—C1—C7—N1 | −169.5 (1) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1o···N1 | 0.83 (2) | 1.87 (2) | 2.588 (2) | 144 (2) |
N2—H2n···O2i | 0.84 (2) | 2.09 (2) | 2.911 (2) | 167 (2) |
Symmetry code: (i) x−1/2, −y+3/2, z. |