N′-[1-(4-Chloro­phen­yl)ethyl­idene]acetohydrazide

In the title compound, C₁₀H₁₁ClN₂O, the dihedral angle between the acetohydrazide group and the aromatic ring is 33.76 (9)°. In the crystal, inversion dimers linked by pairs of N—H...O hydrogen bonds generate R₂²(8) loops.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.046
• wR factor = 0.164
• Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT350_ALERT_3_C Short   C-H Bond (0.96A)   C3     -   H3B    ...       0.82 Ang.
PLAT390_ALERT_3_C Deviating Methyl C3      X-C-H Bond Angle ......     116.30 Deg.
PLAT391_ALERT_3_C Deviating Methyl C3      H-C-H Bond Angle ......     100.00 Deg.
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          3
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         22
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         24

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level G
PUBL013_ALERT_1_G The _publ_section_comment (discussion of study) is
            missing. This is required for a full paper submission (but is
            optional for an electronic paper).

   0 ALERT level A = Data missing that is essential or data in wrong format
   1 ALERT level G = General alerts. Data that may be required is missing

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Related literature

For a related structure, see: Li & Jian (2008).

S1. Experimental

A mixture of 4-fluorobenzophenone (0.02 mol) and acethydrazide (0.02 mol) was stirred in refluxing ethanol(30 ml) for 2 h to afford the title compound (yield 82%). Yellow bars of (I) were obtained by recrystallization from acetic ether at room temperature.

S2. Refinement

All H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H and N—H distances in the range 0.93–0.97Å and 0.86 Å, and with U_iso(H) = 1.2U_eq of the parent atoms.

Structure description

For a related structure, see: Li & Jian (2008).

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level.

N'-[1-(4-Chlorophenyl)ethylidene]acetohydrazide

Crystal data

C10H11ClN2O	F(000) = 440
Mr = 210.66	Dx = 1.333 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2368 reflections
a = 15.944 (3) Å	θ = 3.1–27.5°
b = 5.0061 (10) Å	µ = 0.33 mm^−1
c = 13.950 (3) Å	T = 293 K
β = 109.45 (3)°	Bar, yellow
V = 1049.9 (4) Å^3	0.25 × 0.20 × 0.20 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	1840 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Graphite monochromator	θmax = 27.5°, θmin = 3.1°
phi and ω scans	h = −20→20
9225 measured reflections	k = −6→6
2368 independent reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.22	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
2368 reflections	(Δ/σ)max < 0.001
143 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

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	0.05552 (4)	0.51605 (12)	0.20233 (5)	0.0784 (3)
O1	0.58233 (7)	−0.3084 (2)	0.08042 (9)	0.0515 (3)
N2	0.43948 (8)	−0.2513 (3)	0.06514 (10)	0.0437 (3)
N1	0.37755 (9)	−0.1121 (3)	0.09450 (10)	0.0450 (3)
C4	0.29443 (11)	−0.1619 (3)	0.04835 (12)	0.0449 (4)
C5	0.23285 (11)	−0.0057 (3)	0.08658 (12)	0.0449 (4)
C2	0.52624 (10)	−0.1844 (3)	0.10492 (11)	0.0409 (3)
C8	0.12309 (12)	0.3099 (3)	0.15743 (15)	0.0544 (4)
C7	0.20770 (13)	0.2495 (4)	0.22141 (14)	0.0598 (5)
H7A	0.2280	0.3142	0.2877	0.072*
C6	0.26121 (11)	0.0927 (4)	0.18559 (13)	0.0544 (4)
H6A	0.3181	0.0507	0.2287	0.065*
C10	0.14651 (12)	0.0543 (4)	0.02497 (14)	0.0572 (5)
H10A	0.1251	−0.0132	−0.0408	0.069*
C1	0.55118 (11)	0.0442 (3)	0.17832 (14)	0.0517 (4)
H1B	0.6144	0.0700	0.2004	0.078*
H1C	0.5332	0.0054	0.2360	0.078*
H1D	0.5219	0.2036	0.1456	0.078*
C9	0.09182 (12)	0.2137 (4)	0.06054 (15)	0.0620 (5)
H9A	0.0344	0.2544	0.0186	0.074*
C3	0.25881 (16)	−0.3524 (5)	−0.0385 (2)	0.0663 (6)
H2A	0.4257 (13)	−0.391 (4)	0.0186 (17)	0.062 (5)*
H3A	0.197 (2)	−0.372 (5)	−0.064 (2)	0.106 (9)*
H3B	0.279 (3)	−0.503 (7)	−0.022 (3)	0.155 (16)*
H3C	0.278 (2)	−0.321 (6)	−0.094 (2)	0.115 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0715 (4)	0.0887 (5)	0.0850 (5)	0.0221 (3)	0.0396 (3)	0.0014 (3)
O1	0.0511 (6)	0.0533 (6)	0.0489 (7)	0.0016 (5)	0.0151 (5)	−0.0108 (5)
N2	0.0479 (7)	0.0422 (7)	0.0401 (7)	0.0027 (6)	0.0134 (5)	−0.0058 (5)
N1	0.0475 (7)	0.0469 (7)	0.0399 (7)	0.0038 (6)	0.0137 (5)	−0.0018 (5)
C4	0.0495 (8)	0.0424 (8)	0.0417 (8)	−0.0018 (6)	0.0138 (6)	0.0016 (6)
C5	0.0462 (9)	0.0451 (8)	0.0414 (9)	−0.0024 (6)	0.0119 (7)	0.0029 (6)
C2	0.0510 (8)	0.0378 (7)	0.0325 (7)	0.0033 (6)	0.0122 (6)	0.0004 (5)
C8	0.0520 (9)	0.0554 (9)	0.0615 (11)	0.0043 (7)	0.0267 (8)	0.0037 (8)
C7	0.0601 (10)	0.0706 (11)	0.0469 (10)	0.0085 (9)	0.0154 (8)	−0.0030 (8)
C6	0.0501 (9)	0.0641 (10)	0.0442 (9)	0.0074 (8)	0.0092 (7)	−0.0016 (7)
C10	0.0466 (9)	0.0701 (11)	0.0496 (10)	−0.0019 (8)	0.0089 (7)	−0.0065 (8)
C1	0.0571 (10)	0.0488 (9)	0.0491 (10)	−0.0064 (7)	0.0175 (7)	−0.0115 (7)
C9	0.0429 (8)	0.0705 (11)	0.0663 (12)	0.0032 (8)	0.0097 (8)	0.0008 (9)
C3	0.0595 (12)	0.0661 (13)	0.0687 (14)	−0.0060 (10)	0.0154 (10)	−0.0225 (10)

Geometric parameters (Å, º)

Cl1—C8	1.7512 (17)	C7—C6	1.370 (2)
O1—C2	1.2269 (18)	C7—H7A	0.9300
N2—C2	1.350 (2)	C6—H6A	0.9300
N2—N1	1.3773 (17)	C10—C9	1.390 (3)
N2—H2A	0.93 (2)	C10—H10A	0.9300
N1—C4	1.290 (2)	C1—H1B	0.9600
C4—C5	1.486 (2)	C1—H1C	0.9600
C4—C3	1.497 (2)	C1—H1D	0.9600
C5—C10	1.391 (2)	C9—H9A	0.9300
C5—C6	1.392 (2)	C3—H3A	0.93 (3)
C2—C1	1.498 (2)	C3—H3B	0.83 (4)
C8—C9	1.363 (3)	C3—H3C	0.94 (3)
C8—C7	1.381 (3)
C2—N2—N1	119.36 (13)	C7—C6—H6A	119.1
C2—N2—H2A	116.5 (12)	C5—C6—H6A	119.1
N1—N2—H2A	124.2 (12)	C9—C10—C5	120.84 (17)
C4—N1—N2	118.22 (13)	C9—C10—H10A	119.6
N1—C4—C5	114.25 (13)	C5—C10—H10A	119.6
N1—C4—C3	125.23 (16)	C2—C1—H1B	109.5
C5—C4—C3	120.50 (15)	C2—C1—H1C	109.5
C10—C5—C6	117.66 (16)	H1B—C1—H1C	109.5
C10—C5—C4	121.86 (15)	C2—C1—H1D	109.5
C6—C5—C4	120.46 (14)	H1B—C1—H1D	109.5
O1—C2—N2	120.14 (14)	H1C—C1—H1D	109.5
O1—C2—C1	121.64 (14)	C8—C9—C10	119.41 (16)
N2—C2—C1	118.22 (14)	C8—C9—H9A	120.3
C9—C8—C7	121.30 (16)	C10—C9—H9A	120.3
C9—C8—Cl1	119.82 (14)	C4—C3—H3A	116.6 (17)
C7—C8—Cl1	118.88 (15)	C4—C3—H3B	110 (3)
C6—C7—C8	118.87 (17)	H3A—C3—H3B	106 (3)
C6—C7—H7A	120.6	C4—C3—H3C	115.3 (18)
C8—C7—H7A	120.6	H3A—C3—H3C	107 (2)
C7—C6—C5	121.89 (16)	H3B—C3—H3C	101 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1^i	0.93 (2)	2.02 (2)	2.9384 (18)	170.3 (18)

Symmetry code: (i) −x+1, −y−1, −z.