5-Chloro­salicylaldehyde benzoyl­hydrazone

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.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3	Block, yellow
Z = 4	0.39 × 0.28 × 0.21 mm

Data collection

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

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.030	w = 1/[σ^2(Fo^2) + (0.0616P)^2 + 0.0336P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 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+0.001xFc^2λ^3/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O2^i	0.84 (2)	2.09 (2)	2.911 (2)	167 (2)

Symmetry code: (i) x−1/2, −y+3/2, z.