1-Chloro-1-[(4-methyl­phen­yl)hydrazinyl­idene]propan-2-one

Asiri, A.M.; Al-Youbi, A.O.; Zayed, M.E.M.; Ng, S.W.

doi:10.1107/S1600536811026419

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1964

doi:10.1107/S1600536811026419

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1-Chloro-1-[(4-methylphenyl)hydrazinylidene]propan-2-one

Abdullah M. Asiri,^a,^b Abdulrahman O. Al-Youbi,^a Mohie E. M. Zayed ^a and Seik Weng Ng ^c,^a ^*

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, ^bThe Center of Excellence for Advanced Materials Research, King Abdul Aziz University, PO Box 8020 Jeddah, Saudi Arabia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 29 June 2011; accepted 3 July 2011; online 9 July 2011)

The asymmetric unit of the title compound, C₁₀H₁₁ClN₂O, contains two molecules. The non-H atoms of each molecule lie approximately on a plane (r.m.s. deviations = 0.062 and 0.110 Å), and the C=N double bond has a Z-configuration in both independent molecules. In the crystal, adjacent molecules are linked by N—H⋯O_carbonyl hydrogen bonds, forming chains running along [100].

Related literature

For the synthesis, see: Benincori et al. (1990 ); Sayed et al. (2002 ). For background to the title compound, see: Asiri et al. (2010 ).

Experimental

Crystal data

C₁₀H₁₁ClN₂O
M_r = 210.66
Monoclinic, P 2₁
a = 11.0572 (3) Å
b = 7.6570 (2) Å
c = 12.4613 (3) Å
β = 105.063 (3)°
V = 1018.79 (5) Å³
Z = 4
Cu Kα radiation
μ = 3.06 mm⁻¹
T = 100 K
0.20 × 0.02 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.580, T_max = 0.941
3467 measured reflections
2667 independent reflections
2516 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.125
S = 1.06
2667 reflections
266 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.42 e Å⁻³
Absolute structure: Flack (1983 ), 533 Friedel pairs
Flack parameter: 0.17 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2	0.88 (5)	2.12 (5)	2.975 (4)	162 (4)
N4—H4⋯O1ⁱ	0.83 (5)	2.12 (5)	2.909 (4)	159 (4)
Symmetry code: (i) x+1, y, z.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811026419/xu5262sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026419/xu5262Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811026419/xu5262Isup3.cml

checkCIF report

Comment top

We have previously reported the synthesis of ethyl (Z)-2-chloro-2-(2-phenylhydrazin-1-ylidene) acetate by the reaction of benzenediazonium chloride with ethyl 2-chloro-3-oxobutanoate (Asiri et al., 2010). The compound is an ester. In the present study, the use of a substituted benzenediazonium chloride and the methyl ester (instead of the ethyl ester) afforded a 1-chloro-1-(arylhydrazono)-2-propanone. Such ketones are intermediates in the synthesis of pyrazoles (Sayed et al., 2002) and other heterocycles (Benincori et al., 1990). In the 4-methyl substituted compound (Scheme I, Fig. 1), the non-hydrogen atoms lie on a plane [r.m.s. deviation 0.062 and 0.110 Å in the two independent molecules]. (Scheme I, Fig. 1). The C_aryl–N(H)–N═ C(S)═O portion adopts an extended zigzag conformation. Adjacent molecules are linked by an N–H···O_carbonyl hydrogen bond to form a chain running [1 0 0].

Related literature top

For the synthesis, see: Benincori et al. (1990); Sayed et al. (2002). For background to the title compound, see: Asiri et al. (2010).

Experimental top

To a stirred solution of methyl 2-chloro-3-oxobutanoate (1.64 g, 10 mmol) in ethanol (100 ml) was added sodium acetate trihydrate (1.30 g, 10 mmol). The mixture was chilled to 273 K and then treated with a cold solution of p-nitrobenzenediazonium chloride, prepared by diazotizing p-methylaniline (1.07 g, 10 mmol) dissolved in 6M hydrochloric acid (6 ml) with a solution of sodium nitrite (0.70 g, 10 mmol) in water (10 ml). The addition of the diazonium salt solution was carried out with rapid stirring over a period of 20 min. The reaction mixture was stirred for further 15 min. and left for 3 h in refrigerator. The resulting solid was collected by filtration and washed thoroughly with water. The crude product was crystallized from ethanol to give the corresponding hydrazonoyl chloride.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of C₁₀H₁₁ClN₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

1-Chloro-1-[(4-methylphenyl)hydrazinylidene]propan-2-one top

Crystal data top

C₁₀H₁₁ClN₂O	F(000) = 440
M_r = 210.66	D_x = 1.373 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 1695 reflections
a = 11.0572 (3) Å	θ = 3.7–74.0°
b = 7.6570 (2) Å	µ = 3.06 mm⁻¹
c = 12.4613 (3) Å	T = 100 K
β = 105.063 (3)°	Prism, yellow
V = 1018.79 (5) Å³	0.20 × 0.02 × 0.02 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2667 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2516 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.021
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.2°, θ_min = 3.7°
ω scan	h = −13→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −9→9
T_min = 0.580, T_max = 0.941	l = −13→15
3467 measured reflections

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)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.125	w = 1/[σ²(F_o²) + (0.0867P)² + 0.3419P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
2667 reflections	Δρ_max = 0.31 e Å⁻³
266 parameters	Δρ_min = −0.42 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 533 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.17 (2)

Crystal data top

C₁₀H₁₁ClN₂O	V = 1018.79 (5) Å³
M_r = 210.66	Z = 4
Monoclinic, P2₁	Cu Kα radiation
a = 11.0572 (3) Å	µ = 3.06 mm⁻¹
b = 7.6570 (2) Å	T = 100 K
c = 12.4613 (3) Å	0.20 × 0.02 × 0.02 mm
β = 105.063 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2667 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2516 reflections with I > 2σ(I)
T_min = 0.580, T_max = 0.941	R_int = 0.021
3467 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.125	Δρ_max = 0.31 e Å⁻³
S = 1.06	Δρ_min = −0.42 e Å⁻³
2667 reflections	Absolute structure: Flack (1983), 533 Friedel pairs
266 parameters	Absolute structure parameter: 0.17 (2)
1 restraint

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.22799 (7)	0.50001 (13)	0.90675 (6)	0.0252 (2)
Cl2	0.75288 (7)	0.52179 (14)	1.00248 (6)	0.0252 (2)
N1	0.2864 (2)	0.4827 (4)	1.1276 (2)	0.0187 (6)
N2	0.3920 (3)	0.4043 (4)	1.1235 (2)	0.0195 (6)
H2	0.416 (4)	0.391 (7)	1.062 (4)	0.035 (13)*
N3	0.7037 (2)	0.4842 (4)	0.7819 (2)	0.0193 (6)
N4	0.8068 (3)	0.5762 (4)	0.7850 (2)	0.0201 (6)
H4	0.853 (5)	0.615 (7)	0.844 (4)	0.035 (13)*
O1	0.0213 (2)	0.6872 (4)	0.9612 (2)	0.0297 (7)
O2	0.5199 (3)	0.3196 (4)	0.9474 (2)	0.0281 (6)
C1	0.0693 (3)	0.6493 (6)	1.1582 (3)	0.0253 (8)
H1A	0.0074	0.7420	1.1556	0.038*
H1B	0.1477	0.6800	1.2125	0.038*
H1C	0.0373	0.5391	1.1800	0.038*
C2	0.0928 (3)	0.6290 (6)	1.0454 (3)	0.0225 (8)
C3	0.2071 (3)	0.5347 (5)	1.0390 (3)	0.0207 (7)
C4	0.4745 (3)	0.3415 (5)	1.2216 (3)	0.0177 (7)
C5	0.5915 (3)	0.2783 (5)	1.2169 (3)	0.0207 (7)
H5	0.6156	0.2824	1.1491	0.025*
C6	0.6723 (3)	0.2097 (5)	1.3117 (3)	0.0212 (7)
H6	0.7515	0.1664	1.3077	0.025*
C7	0.6406 (3)	0.2026 (5)	1.4124 (3)	0.0200 (7)
C8	0.5243 (3)	0.2683 (5)	1.4160 (3)	0.0205 (8)
H8	0.5011	0.2654	1.4842	0.025*
C9	0.4416 (3)	0.3377 (5)	1.3228 (3)	0.0190 (7)
H9	0.3630	0.3825	1.3274	0.023*
C10	0.7273 (3)	0.1199 (6)	1.5139 (3)	0.0255 (8)
H10A	0.7083	0.1659	1.5810	0.038*
H10B	0.8143	0.1473	1.5154	0.038*
H10C	0.7155	−0.0070	1.5108	0.038*
C11	0.4814 (4)	0.2920 (5)	0.7503 (3)	0.0240 (8)
H11A	0.4059	0.2297	0.7562	0.036*
H11B	0.5335	0.2139	0.7190	0.036*
H11C	0.4573	0.3938	0.7019	0.036*
C12	0.5538 (3)	0.3510 (5)	0.8636 (3)	0.0203 (8)
C13	0.6703 (3)	0.4509 (5)	0.8711 (3)	0.0194 (7)
C14	0.8352 (3)	0.6173 (5)	0.6841 (3)	0.0176 (7)
C15	0.9434 (3)	0.7145 (5)	0.6877 (3)	0.0206 (7)
H15	0.9979	0.7478	0.7569	0.025*
C16	0.9699 (3)	0.7618 (5)	0.5883 (3)	0.0220 (8)
H16	1.0423	0.8302	0.5907	0.026*
C17	0.8940 (3)	0.7123 (5)	0.4861 (3)	0.0204 (7)
C18	0.7876 (3)	0.6112 (5)	0.4846 (3)	0.0209 (7)
H18	0.7349	0.5739	0.4154	0.025*
C19	0.7581 (3)	0.5651 (5)	0.5822 (3)	0.0195 (7)
H19	0.6853	0.4977	0.5796	0.023*
C20	0.9210 (4)	0.7668 (6)	0.3778 (3)	0.0263 (8)
H20A	0.8425	0.7988	0.3241	0.040*
H20B	0.9602	0.6695	0.3484	0.040*
H20C	0.9778	0.8673	0.3910	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0246 (4)	0.0350 (5)	0.0168 (4)	−0.0019 (4)	0.0070 (3)	0.0016 (4)
Cl2	0.0246 (4)	0.0320 (5)	0.0193 (4)	−0.0022 (4)	0.0065 (3)	−0.0005 (4)
N1	0.0137 (12)	0.0207 (17)	0.0231 (13)	−0.0041 (12)	0.0074 (11)	−0.0008 (13)
N2	0.0191 (14)	0.0255 (17)	0.0158 (13)	−0.0014 (13)	0.0082 (12)	0.0000 (12)
N3	0.0170 (13)	0.0199 (17)	0.0230 (13)	0.0019 (12)	0.0089 (11)	0.0016 (13)
N4	0.0201 (14)	0.0242 (16)	0.0176 (14)	−0.0045 (12)	0.0079 (12)	−0.0019 (13)
O1	0.0162 (12)	0.046 (2)	0.0253 (14)	−0.0022 (12)	0.0019 (11)	0.0054 (13)
O2	0.0251 (13)	0.0375 (17)	0.0263 (14)	−0.0004 (12)	0.0146 (11)	0.0041 (12)
C1	0.0190 (16)	0.034 (2)	0.0246 (18)	0.0011 (16)	0.0089 (15)	0.0000 (17)
C2	0.0163 (15)	0.030 (2)	0.0212 (17)	−0.0053 (16)	0.0053 (14)	−0.0001 (16)
C3	0.0189 (15)	0.025 (2)	0.0194 (15)	−0.0068 (16)	0.0079 (13)	−0.0007 (15)
C4	0.0165 (16)	0.0152 (17)	0.0218 (17)	−0.0030 (14)	0.0057 (14)	−0.0003 (14)
C5	0.0194 (17)	0.0233 (19)	0.0217 (17)	0.0007 (15)	0.0096 (14)	−0.0010 (15)
C6	0.0189 (16)	0.0219 (17)	0.0245 (18)	−0.0011 (15)	0.0088 (14)	−0.0003 (15)
C7	0.0195 (16)	0.0182 (17)	0.0206 (17)	−0.0037 (14)	0.0024 (14)	0.0001 (14)
C8	0.0214 (17)	0.0245 (19)	0.0181 (16)	−0.0041 (15)	0.0099 (14)	−0.0036 (15)
C9	0.0172 (16)	0.0243 (18)	0.0172 (16)	−0.0021 (14)	0.0072 (14)	−0.0012 (14)
C10	0.0229 (17)	0.027 (2)	0.0252 (18)	0.0014 (16)	0.0043 (15)	0.0060 (16)
C11	0.0217 (18)	0.028 (2)	0.0217 (18)	−0.0005 (16)	0.0042 (15)	−0.0003 (16)
C12	0.0199 (17)	0.0193 (18)	0.0255 (18)	0.0056 (15)	0.0129 (15)	0.0032 (15)
C13	0.0219 (17)	0.0207 (18)	0.0167 (15)	0.0034 (14)	0.0068 (14)	0.0020 (13)
C14	0.0174 (15)	0.0181 (18)	0.0185 (16)	0.0023 (14)	0.0067 (13)	0.0013 (14)
C15	0.0196 (16)	0.0199 (17)	0.0223 (17)	0.0014 (14)	0.0057 (14)	0.0016 (15)
C16	0.0149 (15)	0.0212 (19)	0.032 (2)	0.0006 (15)	0.0104 (15)	0.0019 (16)
C17	0.0218 (17)	0.0204 (17)	0.0220 (17)	0.0023 (15)	0.0108 (14)	0.0014 (15)
C18	0.0198 (16)	0.0244 (19)	0.0186 (16)	0.0049 (15)	0.0050 (14)	0.0002 (14)
C19	0.0171 (15)	0.0189 (18)	0.0245 (16)	0.0000 (13)	0.0087 (14)	−0.0015 (14)
C20	0.0234 (18)	0.035 (2)	0.0237 (18)	0.0013 (17)	0.0109 (15)	0.0076 (17)

Geometric parameters (Å, º) top

Cl1—C3	1.743 (3)	C8—C9	1.384 (5)
Cl2—C13	1.742 (4)	C8—H8	0.9500
N1—C3	1.281 (4)	C9—H9	0.9500
N1—N2	1.326 (4)	C10—H10A	0.9800
N2—C4	1.407 (5)	C10—H10B	0.9800
N2—H2	0.88 (5)	C10—H10C	0.9800
N3—C13	1.283 (4)	C11—C12	1.500 (5)
N3—N4	1.332 (4)	C11—H11A	0.9800
N4—C14	1.409 (4)	C11—H11B	0.9800
N4—H4	0.83 (5)	C11—H11C	0.9800
O1—C2	1.221 (5)	C12—C13	1.480 (5)
O2—C12	1.222 (4)	C14—C19	1.391 (5)
C1—C2	1.502 (5)	C14—C15	1.399 (5)
C1—H1A	0.9800	C15—C16	1.393 (5)
C1—H1B	0.9800	C15—H15	0.9500
C1—H1C	0.9800	C16—C17	1.383 (5)
C2—C3	1.477 (5)	C16—H16	0.9500
C4—C5	1.397 (5)	C17—C18	1.404 (5)
C4—C9	1.399 (5)	C17—C20	1.515 (5)
C5—C6	1.386 (5)	C18—C19	1.385 (5)
C5—H5	0.9500	C18—H18	0.9500
C6—C7	1.389 (5)	C19—H19	0.9500
C6—H6	0.9500	C20—H20A	0.9800
C7—C8	1.391 (5)	C20—H20B	0.9800
C7—C10	1.513 (5)	C20—H20C	0.9800

C3—N1—N2	121.3 (3)	H10A—C10—H10B	109.5
N1—N2—C4	120.0 (3)	C7—C10—H10C	109.5
N1—N2—H2	123 (3)	H10A—C10—H10C	109.5
C4—N2—H2	117 (3)	H10B—C10—H10C	109.5
C13—N3—N4	121.1 (3)	C12—C11—H11A	109.5
N3—N4—C14	118.7 (3)	C12—C11—H11B	109.5
N3—N4—H4	123 (3)	H11A—C11—H11B	109.5
C14—N4—H4	118 (3)	C12—C11—H11C	109.5
C2—C1—H1A	109.5	H11A—C11—H11C	109.5
C2—C1—H1B	109.5	H11B—C11—H11C	109.5
H1A—C1—H1B	109.5	O2—C12—C13	120.2 (3)
C2—C1—H1C	109.5	O2—C12—C11	122.5 (3)
H1A—C1—H1C	109.5	C13—C12—C11	117.3 (3)
H1B—C1—H1C	109.5	N3—C13—C12	119.3 (3)
O1—C2—C3	120.3 (3)	N3—C13—Cl2	123.6 (3)
O1—C2—C1	122.3 (3)	C12—C13—Cl2	117.1 (3)
C3—C2—C1	117.4 (3)	C19—C14—C15	119.9 (3)
N1—C3—C2	120.6 (3)	C19—C14—N4	121.6 (3)
N1—C3—Cl1	122.6 (3)	C15—C14—N4	118.5 (3)
C2—C3—Cl1	116.8 (3)	C16—C15—C14	119.0 (3)
C5—C4—C9	119.4 (3)	C16—C15—H15	120.5
C5—C4—N2	118.7 (3)	C14—C15—H15	120.5
C9—C4—N2	121.9 (3)	C17—C16—C15	122.0 (3)
C6—C5—C4	119.6 (3)	C17—C16—H16	119.0
C6—C5—H5	120.2	C15—C16—H16	119.0
C4—C5—H5	120.2	C16—C17—C18	118.0 (3)
C5—C6—C7	121.8 (3)	C16—C17—C20	122.1 (3)
C5—C6—H6	119.1	C18—C17—C20	119.9 (3)
C7—C6—H6	119.1	C19—C18—C17	121.1 (3)
C6—C7—C8	117.8 (3)	C19—C18—H18	119.5
C6—C7—C10	121.1 (3)	C17—C18—H18	119.5
C8—C7—C10	121.0 (3)	C18—C19—C14	120.0 (3)
C9—C8—C7	121.8 (3)	C18—C19—H19	120.0
C9—C8—H8	119.1	C14—C19—H19	120.0
C7—C8—H8	119.1	C17—C20—H20A	109.5
C8—C9—C4	119.6 (3)	C17—C20—H20B	109.5
C8—C9—H9	120.2	H20A—C20—H20B	109.5
C4—C9—H9	120.2	C17—C20—H20C	109.5
C7—C10—H10A	109.5	H20A—C20—H20C	109.5
C7—C10—H10B	109.5	H20B—C20—H20C	109.5

C3—N1—N2—C4	−177.1 (3)	N2—C4—C9—C8	177.5 (4)
C13—N3—N4—C14	−176.5 (3)	N4—N3—C13—C12	178.9 (3)
N2—N1—C3—C2	−177.1 (3)	N4—N3—C13—Cl2	0.6 (5)
N2—N1—C3—Cl1	2.5 (5)	O2—C12—C13—N3	−179.3 (3)
O1—C2—C3—N1	175.7 (4)	C11—C12—C13—N3	0.7 (5)
C1—C2—C3—N1	−4.4 (5)	O2—C12—C13—Cl2	−0.9 (5)
O1—C2—C3—Cl1	−3.9 (5)	C11—C12—C13—Cl2	179.1 (3)
C1—C2—C3—Cl1	176.0 (3)	N3—N4—C14—C19	0.4 (5)
N1—N2—C4—C5	−172.5 (3)	N3—N4—C14—C15	179.8 (3)
N1—N2—C4—C9	8.7 (5)	C19—C14—C15—C16	1.9 (5)
C9—C4—C5—C6	1.3 (6)	N4—C14—C15—C16	−177.5 (3)
N2—C4—C5—C6	−177.6 (3)	C14—C15—C16—C17	−1.5 (6)
C4—C5—C6—C7	−0.4 (6)	C15—C16—C17—C18	0.0 (6)
C5—C6—C7—C8	−0.5 (6)	C15—C16—C17—C20	178.7 (4)
C5—C6—C7—C10	177.2 (4)	C16—C17—C18—C19	1.1 (5)
C6—C7—C8—C9	0.5 (6)	C20—C17—C18—C19	−177.6 (4)
C10—C7—C8—C9	−177.2 (4)	C17—C18—C19—C14	−0.7 (5)
C7—C8—C9—C4	0.5 (6)	C15—C14—C19—C18	−0.9 (5)
C5—C4—C9—C8	−1.3 (6)	N4—C14—C19—C18	178.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.88 (5)	2.12 (5)	2.975 (4)	162 (4)
N4—H4···O1ⁱ	0.83 (5)	2.12 (5)	2.909 (4)	159 (4)

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₁ClN₂O
M_r	210.66
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	11.0572 (3), 7.6570 (2), 12.4613 (3)
β (°)	105.063 (3)
V (Å³)	1018.79 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	3.06
Crystal size (mm)	0.20 × 0.02 × 0.02

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.580, 0.941
No. of measured, independent and observed [I > 2σ(I)] reflections	3467, 2667, 2516
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.125, 1.06
No. of reflections	2667
No. of parameters	266
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.42
Absolute structure	Flack (1983), 533 Friedel pairs
Absolute structure parameter	0.17 (2)

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2	0.88 (5)	2.12 (5)	2.975 (4)	162 (4)
N4—H4···O1ⁱ	0.83 (5)	2.12 (5)	2.909 (4)	159 (4)

Symmetry code: (i) x+1, y, z.

Acknowledgements

We thank King Abdulaziz University and the University of Malaya for supporting this study.

References

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