N′-(2,4-Dichloro­benzyl­idene)benzohydrazide

The asymmetric unit of the title compound, C₁₄H₁₀Cl₂N₂O, comprises two independent mol­ecules, in which the dihedral angles between the terminal phenyl and substituted benzene rings are 21.28 (10) and 39.60 (12)°. N—H...O, C—H...O and C—H...Cl hydrogen bonds stabilize the conformations of the mol­ecules and also stabilize the structure in the solid state.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.044
• wR factor = 0.115
• Data-to-parameter ratio = 18.6

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

N'-(2,4-Dichlorobenzylidene)benzohydrazide

Crystal data

C14H10Cl2N2O	F(000) = 1200
Mr = 293.14	Dx = 1.427 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3851 reflections
a = 10.5668 (9) Å	θ = 2.3–24.7°
b = 17.8266 (15) Å	µ = 0.47 mm^−1
c = 14.9814 (13) Å	T = 294 K
β = 104.734 (1)°	Prism, colorless
V = 2729.3 (4) Å^3	0.46 × 0.34 × 0.22 mm
Z = 8

Data collection

Bruker SMART CCD area-detector diffractometer	6557 independent reflections
Radiation source: fine-focus sealed tube	4110 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 28.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
Tmin = 0.822, Tmax = 0.906	k = −22→23
18247 measured reflections	l = −10→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.0438P)^2 + 0.8233P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
6557 reflections	Δρmax = 0.46 e Å^−3
352 parameters	Δρmin = −0.49 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0027 (4)

Special details

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 > σ(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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	1.38504 (5)	0.20983 (4)	0.41584 (5)	0.0699 (2)
Cl2	0.88475 (7)	0.24961 (5)	0.23264 (5)	0.1014 (3)
Cl3	0.88072 (9)	−0.08510 (4)	0.45449 (7)	0.1058 (3)
Cl4	0.51961 (7)	−0.01465 (4)	0.14726 (5)	0.0832 (2)
O1	0.70797 (13)	0.33515 (8)	0.63408 (10)	0.0543 (4)
O2	0.55680 (13)	0.36003 (8)	0.27861 (10)	0.0565 (4)
N1	0.68266 (15)	0.33785 (9)	0.48053 (12)	0.0446 (4)
H1	0.6392 (19)	0.3479 (11)	0.4253 (15)	0.049 (6)*
N2	0.80913 (14)	0.31298 (9)	0.48992 (11)	0.0422 (4)
N3	0.44711 (16)	0.26070 (10)	0.20264 (12)	0.0459 (4)
H3	0.376 (2)	0.2422 (12)	0.1660 (15)	0.055 (6)*
N4	0.54188 (15)	0.21222 (9)	0.25064 (11)	0.0452 (4)
C1	0.64115 (17)	0.35188 (10)	0.55666 (14)	0.0408 (4)
C2	0.51155 (17)	0.38950 (10)	0.54260 (14)	0.0418 (4)
C3	0.4711 (2)	0.40801 (12)	0.62038 (16)	0.0551 (5)
H3A	0.5227	0.3952	0.6785	0.066*
C4	0.3543 (2)	0.44560 (14)	0.61236 (19)	0.0675 (7)
H4	0.3275	0.4579	0.6651	0.081*
C5	0.2771 (2)	0.46493 (14)	0.5265 (2)	0.0674 (7)
H5	0.1988	0.4904	0.5213	0.081*
C6	0.3163 (2)	0.44647 (14)	0.44916 (18)	0.0642 (6)
H6	0.2639	0.4589	0.3912	0.077*
C7	0.43314 (19)	0.40946 (12)	0.45667 (15)	0.0529 (5)
H7	0.4597	0.3978	0.4037	0.063*
C8	0.84056 (18)	0.30186 (11)	0.41445 (14)	0.0445 (5)
H8	0.7782	0.3079	0.3586	0.053*
C9	0.97392 (18)	0.27966 (10)	0.41474 (13)	0.0403 (4)
C10	1.0059 (2)	0.25464 (12)	0.33544 (14)	0.0502 (5)
C11	1.1309 (2)	0.23305 (12)	0.33454 (15)	0.0521 (5)
H11	1.1492	0.2156	0.2807	0.063*
C12	1.22741 (18)	0.23794 (11)	0.41503 (14)	0.0454 (5)
C13	1.20168 (19)	0.26447 (13)	0.49479 (15)	0.0533 (5)
H13	1.2685	0.2685	0.5486	0.064*
C14	1.07595 (19)	0.28488 (12)	0.49397 (14)	0.0492 (5)
H14	1.0587	0.3027	0.5480	0.059*
C15	0.45857 (18)	0.33424 (11)	0.22545 (13)	0.0448 (5)
C16	0.34305 (19)	0.38301 (12)	0.18442 (14)	0.0474 (5)
C17	0.2187 (2)	0.35618 (13)	0.14593 (17)	0.0640 (6)
H17	0.2039	0.3047	0.1411	0.077*
C18	0.1156 (2)	0.40550 (16)	0.1144 (2)	0.0789 (8)
H18	0.0323	0.3869	0.0879	0.095*
C19	0.1356 (3)	0.48106 (16)	0.12205 (19)	0.0778 (8)
H19	0.0659	0.5140	0.1016	0.093*
C20	0.2584 (3)	0.50810 (15)	0.1598 (2)	0.0875 (9)
H20	0.2722	0.5596	0.1647	0.105*
C21	0.3621 (2)	0.45974 (13)	0.19068 (18)	0.0706 (7)
H21	0.4454	0.4789	0.2159	0.085*
C22	0.52433 (18)	0.14344 (12)	0.22914 (14)	0.0463 (5)
H22	0.4552	0.1287	0.1803	0.056*
C23	0.61434 (18)	0.08768 (11)	0.28220 (14)	0.0445 (5)
C24	0.61889 (19)	0.01409 (12)	0.25238 (16)	0.0511 (5)
C25	0.7017 (2)	−0.03884 (12)	0.30430 (19)	0.0621 (6)
H25	0.7037	−0.0876	0.2828	0.074*
C26	0.7808 (2)	−0.01794 (13)	0.38806 (19)	0.0649 (6)
C27	0.7791 (2)	0.05413 (14)	0.42114 (18)	0.0704 (7)
H27	0.8326	0.0675	0.4784	0.084*
C28	0.6965 (2)	0.10597 (12)	0.36779 (16)	0.0581 (6)
H28	0.6957	0.1547	0.3897	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0439 (3)	0.0837 (4)	0.0862 (5)	0.0057 (3)	0.0241 (3)	−0.0108 (3)
Cl2	0.0794 (4)	0.1611 (8)	0.0480 (4)	0.0467 (5)	−0.0124 (3)	−0.0368 (4)
Cl3	0.1126 (6)	0.0776 (5)	0.1202 (7)	0.0352 (4)	0.0168 (5)	0.0416 (5)
Cl4	0.0701 (4)	0.0810 (5)	0.0903 (5)	−0.0042 (3)	0.0053 (4)	−0.0332 (4)
O1	0.0441 (7)	0.0736 (10)	0.0432 (8)	0.0127 (7)	0.0074 (6)	0.0082 (7)
O2	0.0490 (8)	0.0581 (9)	0.0508 (9)	0.0005 (7)	−0.0086 (7)	−0.0058 (7)
N1	0.0358 (8)	0.0539 (10)	0.0411 (10)	0.0111 (7)	0.0045 (8)	0.0021 (8)
N2	0.0340 (8)	0.0470 (9)	0.0440 (9)	0.0068 (7)	0.0070 (7)	0.0004 (7)
N3	0.0383 (9)	0.0497 (10)	0.0429 (9)	0.0040 (7)	−0.0018 (7)	−0.0018 (8)
N4	0.0378 (8)	0.0505 (10)	0.0450 (9)	0.0052 (7)	0.0065 (7)	0.0034 (8)
C1	0.0366 (9)	0.0399 (10)	0.0448 (11)	−0.0009 (8)	0.0083 (9)	0.0004 (8)
C2	0.0340 (9)	0.0394 (10)	0.0520 (12)	−0.0002 (8)	0.0110 (9)	0.0002 (9)
C3	0.0460 (11)	0.0628 (13)	0.0571 (14)	0.0034 (10)	0.0144 (10)	−0.0024 (11)
C4	0.0562 (14)	0.0763 (16)	0.0776 (18)	0.0077 (12)	0.0310 (13)	−0.0084 (14)
C5	0.0424 (12)	0.0707 (15)	0.091 (2)	0.0145 (11)	0.0203 (13)	0.0017 (14)
C6	0.0443 (12)	0.0754 (16)	0.0701 (16)	0.0152 (11)	0.0097 (11)	0.0093 (13)
C7	0.0436 (11)	0.0608 (13)	0.0530 (13)	0.0105 (10)	0.0099 (10)	0.0016 (10)
C8	0.0418 (10)	0.0475 (11)	0.0402 (11)	0.0073 (8)	0.0034 (9)	−0.0009 (9)
C9	0.0413 (10)	0.0409 (10)	0.0379 (10)	0.0045 (8)	0.0087 (8)	0.0009 (8)
C10	0.0514 (12)	0.0570 (12)	0.0373 (11)	0.0110 (10)	0.0022 (9)	−0.0053 (9)
C11	0.0560 (13)	0.0586 (13)	0.0438 (12)	0.0099 (10)	0.0164 (10)	−0.0070 (10)
C12	0.0394 (10)	0.0462 (11)	0.0529 (12)	0.0016 (8)	0.0160 (9)	0.0008 (9)
C13	0.0406 (11)	0.0751 (14)	0.0416 (11)	0.0012 (10)	0.0053 (9)	−0.0023 (11)
C14	0.0432 (11)	0.0707 (14)	0.0345 (10)	0.0030 (10)	0.0115 (9)	−0.0028 (10)
C15	0.0436 (11)	0.0522 (12)	0.0349 (10)	0.0038 (9)	0.0033 (9)	−0.0006 (9)
C16	0.0470 (11)	0.0518 (12)	0.0397 (11)	0.0061 (9)	0.0042 (9)	−0.0033 (9)
C17	0.0483 (12)	0.0572 (13)	0.0775 (17)	0.0048 (10)	−0.0004 (11)	−0.0004 (12)
C18	0.0485 (13)	0.0836 (19)	0.094 (2)	0.0126 (13)	−0.0016 (13)	−0.0014 (16)
C19	0.0724 (17)	0.0747 (18)	0.0779 (19)	0.0317 (14)	0.0039 (14)	−0.0020 (14)
C20	0.090 (2)	0.0551 (15)	0.099 (2)	0.0185 (14)	−0.0080 (17)	−0.0078 (15)
C21	0.0654 (15)	0.0538 (14)	0.0776 (17)	0.0076 (11)	−0.0093 (13)	−0.0093 (12)
C22	0.0386 (10)	0.0535 (12)	0.0453 (12)	−0.0001 (9)	0.0080 (9)	−0.0026 (9)
C23	0.0374 (10)	0.0447 (11)	0.0525 (12)	−0.0027 (8)	0.0132 (9)	0.0023 (9)
C24	0.0402 (10)	0.0524 (12)	0.0636 (14)	−0.0053 (9)	0.0186 (10)	−0.0057 (10)
C25	0.0572 (13)	0.0436 (12)	0.0909 (19)	0.0003 (10)	0.0289 (13)	0.0027 (12)
C26	0.0600 (14)	0.0563 (14)	0.0783 (18)	0.0108 (11)	0.0173 (13)	0.0212 (13)
C27	0.0714 (16)	0.0636 (15)	0.0647 (16)	0.0072 (13)	−0.0037 (13)	0.0078 (13)
C28	0.0613 (13)	0.0462 (12)	0.0597 (14)	0.0024 (10)	0.0026 (11)	0.0009 (10)

Geometric parameters (Å, º)

Cl1—C12	1.7364 (19)	C10—C11	1.379 (3)
Cl2—C10	1.737 (2)	C11—C12	1.370 (3)
Cl3—C26	1.733 (2)	C11—H11	0.9300
Cl4—C24	1.733 (2)	C12—C13	1.375 (3)
O1—C1	1.231 (2)	C13—C14	1.375 (3)
O2—C15	1.226 (2)	C13—H13	0.9300
N1—C1	1.346 (3)	C14—H14	0.9300
N1—N2	1.381 (2)	C15—C16	1.497 (3)
N1—H1	0.86 (2)	C16—C17	1.380 (3)
N2—C8	1.272 (2)	C16—C21	1.382 (3)
N3—C15	1.352 (3)	C17—C18	1.386 (3)
N3—N4	1.379 (2)	C17—H17	0.9300
N3—H3	0.88 (2)	C18—C19	1.364 (4)
N4—C22	1.269 (3)	C18—H18	0.9300
C1—C2	1.491 (2)	C19—C20	1.365 (4)
C2—C3	1.379 (3)	C19—H19	0.9300
C2—C7	1.388 (3)	C20—C21	1.378 (3)
C3—C4	1.383 (3)	C20—H20	0.9300
C3—H3A	0.9300	C21—H21	0.9300
C4—C5	1.380 (3)	C22—C23	1.463 (3)
C4—H4	0.9300	C22—H22	0.9300
C5—C6	1.366 (3)	C23—C24	1.391 (3)
C5—H5	0.9300	C23—C28	1.392 (3)
C6—C7	1.379 (3)	C24—C25	1.384 (3)
C6—H6	0.9300	C25—C26	1.370 (3)
C7—H7	0.9300	C25—H25	0.9300
C8—C9	1.463 (3)	C26—C27	1.379 (3)
C8—H8	0.9300	C27—C28	1.378 (3)
C9—C10	1.389 (3)	C27—H27	0.9300
C9—C14	1.389 (3)	C28—H28	0.9300
C1—N1—N2	119.27 (16)	C12—C13—H13	120.4
C1—N1—H1	124.7 (14)	C13—C14—C9	121.89 (19)
N2—N1—H1	115.7 (14)	C13—C14—H14	119.1
C8—N2—N1	115.09 (16)	C9—C14—H14	119.1
C15—N3—N4	117.99 (16)	O2—C15—N3	122.30 (18)
C15—N3—H3	122.0 (14)	O2—C15—C16	121.07 (18)
N4—N3—H3	119.1 (14)	N3—C15—C16	116.61 (17)
C22—N4—N3	115.67 (16)	C17—C16—C21	118.5 (2)
O1—C1—N1	121.40 (17)	C17—C16—C15	124.11 (19)
O1—C1—C2	121.88 (18)	C21—C16—C15	117.23 (19)
N1—C1—C2	116.71 (17)	C16—C17—C18	120.3 (2)
C3—C2—C7	118.82 (18)	C16—C17—H17	119.8
C3—C2—C1	117.31 (18)	C18—C17—H17	119.8
C7—C2—C1	123.81 (18)	C19—C18—C17	120.5 (2)
C2—C3—C4	120.3 (2)	C19—C18—H18	119.8
C2—C3—H3A	119.9	C17—C18—H18	119.8
C4—C3—H3A	119.9	C18—C19—C20	119.6 (2)
C5—C4—C3	120.3 (2)	C18—C19—H19	120.2
C5—C4—H4	119.8	C20—C19—H19	120.2
C3—C4—H4	119.8	C19—C20—C21	120.6 (3)
C6—C5—C4	119.7 (2)	C19—C20—H20	119.7
C6—C5—H5	120.1	C21—C20—H20	119.7
C4—C5—H5	120.1	C20—C21—C16	120.5 (2)
C5—C6—C7	120.3 (2)	C20—C21—H21	119.8
C5—C6—H6	119.9	C16—C21—H21	119.8
C7—C6—H6	119.9	N4—C22—C23	119.05 (18)
C6—C7—C2	120.6 (2)	N4—C22—H22	120.5
C6—C7—H7	119.7	C23—C22—H22	120.5
C2—C7—H7	119.7	C24—C23—C28	116.90 (19)
N2—C8—C9	120.56 (17)	C24—C23—C22	122.50 (19)
N2—C8—H8	119.7	C28—C23—C22	120.56 (18)
C9—C8—H8	119.7	C25—C24—C23	122.1 (2)
C10—C9—C14	116.59 (17)	C25—C24—Cl4	117.35 (17)
C10—C9—C8	121.89 (17)	C23—C24—Cl4	120.56 (17)
C14—C9—C8	121.49 (17)	C26—C25—C24	118.7 (2)
C11—C10—C9	122.69 (18)	C26—C25—H25	120.6
C11—C10—Cl2	117.96 (16)	C24—C25—H25	120.6
C9—C10—Cl2	119.35 (15)	C25—C26—C27	121.5 (2)
C12—C11—C10	118.29 (19)	C25—C26—Cl3	118.58 (19)
C12—C11—H11	120.9	C27—C26—Cl3	119.9 (2)
C10—C11—H11	120.9	C28—C27—C26	118.7 (2)
C11—C12—C13	121.31 (18)	C28—C27—H27	120.6
C11—C12—Cl1	119.06 (16)	C26—C27—H27	120.6
C13—C12—Cl1	119.64 (16)	C27—C28—C23	122.1 (2)
C14—C13—C12	119.18 (19)	C27—C28—H28	118.9
C14—C13—H13	120.4	C23—C28—H28	118.9
C1—N1—N2—C8	−179.31 (18)	C8—C9—C14—C13	−179.7 (2)
C15—N3—N4—C22	177.48 (18)	N4—N3—C15—O2	8.9 (3)
N2—N1—C1—O1	−8.3 (3)	N4—N3—C15—C16	−169.43 (17)
N2—N1—C1—C2	170.93 (16)	O2—C15—C16—C17	−161.2 (2)
O1—C1—C2—C3	2.7 (3)	N3—C15—C16—C17	17.1 (3)
N1—C1—C2—C3	−176.45 (18)	O2—C15—C16—C21	15.0 (3)
O1—C1—C2—C7	179.89 (19)	N3—C15—C16—C21	−166.7 (2)
N1—C1—C2—C7	0.7 (3)	C21—C16—C17—C18	0.0 (4)
C7—C2—C3—C4	0.2 (3)	C15—C16—C17—C18	176.1 (2)
C1—C2—C3—C4	177.5 (2)	C16—C17—C18—C19	−0.8 (4)
C2—C3—C4—C5	0.0 (4)	C17—C18—C19—C20	0.9 (5)
C3—C4—C5—C6	0.3 (4)	C18—C19—C20—C21	−0.4 (5)
C4—C5—C6—C7	−0.8 (4)	C19—C20—C21—C16	−0.4 (5)
C5—C6—C7—C2	0.9 (4)	C17—C16—C21—C20	0.6 (4)
C3—C2—C7—C6	−0.6 (3)	C15—C16—C21—C20	−175.8 (2)
C1—C2—C7—C6	−177.8 (2)	N3—N4—C22—C23	−174.83 (17)
N1—N2—C8—C9	176.43 (16)	N4—C22—C23—C24	−166.58 (19)
N2—C8—C9—C10	168.66 (19)	N4—C22—C23—C28	16.0 (3)
N2—C8—C9—C14	−13.4 (3)	C28—C23—C24—C25	−0.6 (3)
C14—C9—C10—C11	2.4 (3)	C22—C23—C24—C25	−178.10 (19)
C8—C9—C10—C11	−179.6 (2)	C28—C23—C24—Cl4	179.49 (16)
C14—C9—C10—Cl2	−177.83 (16)	C22—C23—C24—Cl4	2.0 (3)
C8—C9—C10—Cl2	0.2 (3)	C23—C24—C25—C26	0.6 (3)
C9—C10—C11—C12	−1.2 (3)	Cl4—C24—C25—C26	−179.54 (18)
Cl2—C10—C11—C12	179.02 (17)	C24—C25—C26—C27	0.1 (4)
C10—C11—C12—C13	−0.8 (3)	C24—C25—C26—Cl3	178.04 (17)
C10—C11—C12—Cl1	179.11 (16)	C25—C26—C27—C28	−0.6 (4)
C11—C12—C13—C14	1.4 (3)	Cl3—C26—C27—C28	−178.6 (2)
Cl1—C12—C13—C14	−178.45 (17)	C26—C27—C28—C23	0.5 (4)
C12—C13—C14—C9	−0.1 (3)	C24—C23—C28—C27	0.1 (3)
C10—C9—C14—C13	−1.7 (3)	C22—C23—C28—C27	177.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1^i	0.88 (2)	2.20 (2)	3.007 (2)	152.7 (19)
N1—H1···O2	0.86 (2)	2.16 (2)	3.005 (2)	169.1 (19)
C7—H7···O2	0.93	2.45	3.372 (3)	172
C8—H8···O2	0.93	2.52	3.332 (2)	146
C11—H11···O1^ii	0.93	2.59	3.522 (3)	178
C13—H13···Cl2^iii	0.93	2.74	3.605 (2)	156
C17—H17···O1^i	0.93	2.50	3.416 (3)	170

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) x+1/2, −y+1/2, z−1/2; (iii) x+1/2, −y+1/2, z+1/2.