(E)-2-[4-(2-Chloro­phen­yl)but-3-en-2-yl­idene]malononitrile

Kang, T.-R.

doi:10.1107/S1600536811037159

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2661

https://doi.org/10.1107/S1600536811037159

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(E)-2-[4-(2-Chlorophenyl)but-3-en-2-ylidene]malononitrile

Tai-Ran Kang ^a ^*

^aCollege of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: kangtairan@sina.com

(Received 11 September 2011; accepted 13 September 2011; online 17 September 2011)

There are two independent but virtually identical molecules in the asymmetric unit of the title compound, C₁₃H₁₉ClN₂. Each molecular skeleton displays an approximately planar structure except for the methyl group [the r.m.s. deviations for all 16 non-H atoms are 0.039 (molecule 1) and 0.056 Å (molecule 2)]. An E configuration is found about each of the C=C bonds. The crystal packing is stabilized by C—H⋯N interactions that connect the independent molecules into supramolecular chains along the c-axis direction.

Related literature

For the use of malononitrile-containing compounds as building blocks in synthesis, see: Liu et al. (2002 ); Sepiol & Milart (1985 ); Zhang et al. (2003 ). For a related structure, see: Kang & Chen (2009 ).

Experimental

Crystal data

C₁₃H₉ClN₂
M_r = 228.67
Triclinic, $[P \overline 1]$
a = 7.7177 (2) Å
b = 11.0539 (5) Å
c = 14.7236 (5) Å
α = 91.260 (3)°
β = 103.992 (3)°
γ = 106.357 (3)°
V = 1163.99 (7) Å³
Z = 4
Cu Kα radiation
μ = 2.67 mm⁻¹
T = 291 K
0.35 × 0.32 × 0.30 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.455, T_max = 0.502
9739 measured reflections
4135 independent reflections
3770 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.140
S = 1.04
4135 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10C⋯N3ⁱ	0.96	2.62	3.564 (3)	166 (1)
Symmetry code: (i) x, y, z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811037159/tk2789sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811037159/tk2789Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811037159/tk2789Isup3.cml

checkCIF report

Comment top

The chemistry of ylidene malononitrile has been studied extensively for ring closure reactions, with compounds containing newly formed five- or six-membered rings, such as indanes (Zhang et al., 2003), naphthalenes (Liu et al., 2002) and benzenes (Sepiol & Milart, 1985) being obtained. Some crystal structures involving ylidene malononitrile groups have been published, including a recent report from our laboratory (Kang & Chen, 2009). As a part of our interest in the synthesis of some complex ring systems, we investigated the title compound (I), which is a diene reagent in the Diels-Alder reaction. We report herein the crystal structure of (I).

Two independent molecules comprise the asymmetric unit of (I), Fig. 1. The molecular skeleton displays an approximately planar arrangement in each case. The chlorobenzene ring and 2-propylidenemalononitrile groups are located on opposite sides of the double bond to which they are attached, showing an E configuration. The crystal packing is stabilized by C—H···N interactions (Table 1).

Related literature top

For the use of malononitrile-containing compounds as building blocks in synthesis, see: Liu et al. (2002); Sepiol & Milart (1985); Zhang et al. (2003). For a related structure, see: Kang & Chen (2009).

Experimental top

2-(Propan-2-ylidene)malononitrile (0.212 g, 2 mmol) and 2-chlorobenzaldehyde (0.28 g, 2 mmol) were dissolved in 2-propanol (2 ml). To the solution was added piperidine (0.017 g, 0.2 mmol). The solution was then stirred for 24 h at 343 K. The reaction mixture was cooled to room temperature and the solution was filtered to obtain a white solid. Recrystallization from hot ethanol afforded the pure compound. Single crystals of (I) were obtained by slow evaporation of its ethyl acetate solution.

Structure description top

For the use of malononitrile-containing compounds as building blocks in synthesis, see: Liu et al. (2002); Sepiol & Milart (1985); Zhang et al. (2003). For a related structure, see: Kang & Chen (2009).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing atom labelling scheme and 30% probability displacement ellipsoids (arbitrary spheres for H atoms).

(E)-2-[4-(2-Chlorophenyl)but-3-en-2-ylidene]malononitrile top

Crystal data top

C₁₃H₉ClN₂	Z = 4
M_r = 228.67	F(000) = 472
Triclinic, P1	D_x = 1.305 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 7.7177 (2) Å	Cell parameters from 6315 reflections
b = 11.0539 (5) Å	θ = 3.1–72.1°
c = 14.7236 (5) Å	µ = 2.67 mm⁻¹
α = 91.260 (3)°	T = 291 K
β = 103.992 (3)°	Block, yellow
γ = 106.357 (3)°	0.35 × 0.32 × 0.30 mm
V = 1163.99 (7) Å³

Data collection top

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer	4135 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	3770 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.027
Detector resolution: 15.9149 pixels mm^-1	θ_max = 67.1°, θ_min = 3.1°
ω scans	h = −9→7
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −13→13
T_min = 0.455, T_max = 0.502	l = −17→17
9739 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0727P)² + 0.290P] where P = (F_o² + 2F_c²)/3
4135 reflections	(Δ/σ)_max = 0.001
291 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₃H₉ClN₂	γ = 106.357 (3)°
M_r = 228.67	V = 1163.99 (7) Å³
Triclinic, P1	Z = 4
a = 7.7177 (2) Å	Cu Kα radiation
b = 11.0539 (5) Å	µ = 2.67 mm⁻¹
c = 14.7236 (5) Å	T = 291 K
α = 91.260 (3)°	0.35 × 0.32 × 0.30 mm
β = 103.992 (3)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 Gemini ultra diffractometer	4135 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	3770 reflections with I > 2σ(I)
T_min = 0.455, T_max = 0.502	R_int = 0.027
9739 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.04	Δρ_max = 0.45 e Å⁻³
4135 reflections	Δρ_min = −0.20 e Å⁻³
291 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C24	0.5347 (2)	0.25777 (17)	0.36952 (12)	0.0541 (4)
C9	0.6600 (2)	0.30400 (18)	0.94779 (12)	0.0536 (4)
C8	0.6947 (3)	0.43885 (18)	0.96046 (13)	0.0562 (4)
H8	0.6495	0.4786	0.9088	0.067*
C1	0.9378 (3)	0.71648 (18)	1.14140 (13)	0.0569 (4)
C23	0.5469 (3)	0.2649 (2)	0.53865 (14)	0.0670 (5)
H23A	0.4703	0.1791	0.5194	0.100*
H23C	0.4796	0.3106	0.5656	0.100*
H23B	0.6592	0.2654	0.5846	0.100*
C22	0.5964 (3)	0.32662 (18)	0.45502 (13)	0.0551 (4)
N1	0.4827 (4)	−0.0031 (2)	0.83682 (16)	0.0942 (7)
C11	0.5561 (3)	0.23861 (18)	0.86407 (13)	0.0574 (4)
C19	0.8945 (3)	0.66283 (18)	0.55896 (14)	0.0588 (5)
C6	0.8253 (2)	0.64747 (17)	1.05665 (12)	0.0524 (4)
C26	0.4247 (3)	0.1281 (2)	0.35739 (15)	0.0697 (5)
C12	0.5155 (3)	0.1042 (2)	0.84862 (15)	0.0679 (5)
C25	0.5774 (3)	0.30988 (19)	0.28661 (13)	0.0600 (5)
C14	0.9546 (3)	0.7332 (2)	0.64619 (15)	0.0651 (5)
C5	0.7504 (3)	0.71784 (19)	0.98811 (14)	0.0613 (5)
H5	0.6738	0.6759	0.9307	0.074*
C4	0.7863 (3)	0.8465 (2)	1.00278 (17)	0.0716 (6)
H4	0.7347	0.8903	0.9557	0.086*
N2	0.4120 (3)	0.3468 (2)	0.72447 (14)	0.0907 (6)
C10	0.7382 (3)	0.2352 (2)	1.02658 (14)	0.0645 (5)
H10A	0.6969	0.1460	1.0073	0.097*
H10C	0.6955	0.2506	1.0806	0.097*
H10B	0.8723	0.2650	1.0423	0.097*
C20	0.7793 (3)	0.53241 (19)	0.54577 (13)	0.0594 (5)
H20	0.7489	0.4972	0.5987	0.071*
C21	0.7120 (3)	0.45749 (18)	0.46499 (13)	0.0577 (4)
H21	0.7412	0.4915	0.4114	0.069*
C7	0.7870 (2)	0.51104 (18)	1.04108 (13)	0.0544 (4)
H7	0.8312	0.4701	1.0922	0.065*
C18	0.9567 (3)	0.7248 (2)	0.48501 (16)	0.0703 (5)
H18	0.9197	0.6815	0.4254	0.084*
C17	1.0704 (3)	0.8474 (2)	0.4987 (2)	0.0855 (7)
H17	1.1080	0.8863	0.4484	0.103*
C2	0.9749 (3)	0.8458 (2)	1.15697 (17)	0.0730 (6)
H2	1.0507	0.8888	1.2142	0.088*
C13	0.4755 (3)	0.2988 (2)	0.78642 (14)	0.0661 (5)
C15	1.0718 (3)	0.8564 (2)	0.6601 (2)	0.0844 (7)
H15	1.1119	0.9008	0.7194	0.101*
C3	0.8988 (3)	0.9107 (2)	1.08720 (19)	0.0776 (6)
H3	0.9233	0.9980	1.0971	0.093*
C16	1.1285 (4)	0.9126 (3)	0.5857 (3)	0.0941 (8)
H16	1.2068	0.9954	0.5947	0.113*
N3	0.6097 (3)	0.3519 (2)	0.22018 (13)	0.0802 (5)
N4	0.3349 (4)	0.0253 (2)	0.34942 (17)	0.1014 (8)
Cl1	1.03787 (8)	0.63948 (6)	1.23196 (4)	0.0778 (2)
Cl2	0.88209 (9)	0.66910 (6)	0.74273 (4)	0.0836 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C24	0.0527 (9)	0.0603 (10)	0.0449 (9)	0.0145 (8)	0.0070 (7)	0.0042 (8)
C9	0.0564 (10)	0.0620 (10)	0.0417 (9)	0.0157 (8)	0.0137 (8)	0.0040 (7)
C8	0.0603 (10)	0.0620 (11)	0.0433 (9)	0.0149 (8)	0.0113 (8)	0.0084 (8)
C1	0.0525 (9)	0.0617 (11)	0.0491 (10)	0.0086 (8)	0.0089 (8)	0.0051 (8)
C23	0.0747 (12)	0.0774 (13)	0.0473 (10)	0.0197 (10)	0.0156 (9)	0.0124 (9)
C22	0.0581 (10)	0.0639 (11)	0.0451 (9)	0.0240 (8)	0.0093 (8)	0.0088 (8)
N1	0.1175 (17)	0.0700 (13)	0.0813 (14)	0.0206 (12)	0.0100 (12)	−0.0096 (11)
C11	0.0626 (10)	0.0653 (11)	0.0435 (9)	0.0187 (9)	0.0129 (8)	0.0020 (8)
C19	0.0597 (10)	0.0621 (11)	0.0544 (11)	0.0267 (9)	0.0044 (8)	0.0055 (8)
C6	0.0483 (9)	0.0575 (10)	0.0474 (9)	0.0100 (7)	0.0115 (7)	0.0075 (7)
C26	0.0694 (12)	0.0719 (14)	0.0546 (11)	0.0062 (10)	0.0094 (10)	0.0008 (9)
C12	0.0750 (13)	0.0696 (13)	0.0526 (11)	0.0178 (10)	0.0094 (10)	−0.0039 (9)
C25	0.0649 (11)	0.0634 (11)	0.0440 (10)	0.0142 (9)	0.0062 (8)	−0.0008 (8)
C14	0.0636 (11)	0.0714 (12)	0.0598 (11)	0.0322 (10)	0.0011 (9)	0.0005 (9)
C5	0.0567 (10)	0.0682 (12)	0.0538 (11)	0.0139 (9)	0.0093 (8)	0.0133 (9)
C4	0.0713 (13)	0.0674 (13)	0.0790 (15)	0.0220 (10)	0.0216 (11)	0.0246 (11)
N2	0.1135 (16)	0.1141 (17)	0.0487 (11)	0.0514 (14)	0.0078 (10)	0.0067 (10)
C10	0.0774 (13)	0.0643 (12)	0.0482 (10)	0.0223 (10)	0.0082 (9)	0.0066 (9)
C20	0.0618 (11)	0.0675 (11)	0.0475 (10)	0.0225 (9)	0.0074 (8)	0.0068 (8)
C21	0.0598 (10)	0.0646 (11)	0.0473 (10)	0.0191 (9)	0.0102 (8)	0.0077 (8)
C7	0.0527 (9)	0.0619 (11)	0.0448 (9)	0.0133 (8)	0.0094 (7)	0.0065 (8)
C18	0.0731 (13)	0.0788 (14)	0.0644 (13)	0.0338 (11)	0.0136 (10)	0.0138 (10)
C17	0.0732 (14)	0.0788 (16)	0.110 (2)	0.0272 (12)	0.0273 (14)	0.0291 (15)
C2	0.0726 (13)	0.0618 (12)	0.0689 (13)	0.0011 (10)	0.0125 (11)	−0.0047 (10)
C13	0.0773 (13)	0.0785 (13)	0.0411 (10)	0.0257 (11)	0.0104 (9)	−0.0009 (9)
C15	0.0735 (14)	0.0753 (15)	0.0921 (18)	0.0239 (12)	−0.0022 (13)	−0.0113 (13)
C3	0.0828 (15)	0.0555 (12)	0.0920 (17)	0.0122 (10)	0.0276 (13)	0.0094 (11)
C16	0.0732 (15)	0.0717 (15)	0.127 (3)	0.0179 (12)	0.0117 (16)	0.0060 (16)
N3	0.0992 (14)	0.0858 (13)	0.0485 (10)	0.0164 (11)	0.0189 (9)	0.0050 (9)
N4	0.1103 (17)	0.0789 (14)	0.0845 (15)	−0.0136 (13)	0.0191 (13)	−0.0043 (11)
Cl1	0.0806 (4)	0.0843 (4)	0.0513 (3)	0.0177 (3)	−0.0067 (2)	0.0067 (2)
Cl2	0.0973 (4)	0.1005 (5)	0.0477 (3)	0.0347 (3)	0.0035 (3)	−0.0035 (3)

Geometric parameters (Å, º) top

C24—C22	1.362 (3)	C25—N3	1.144 (3)
C24—C26	1.427 (3)	C14—C15	1.386 (3)
C24—C25	1.432 (3)	C14—Cl2	1.744 (2)
C9—C11	1.357 (3)	C5—C4	1.372 (3)
C9—C8	1.438 (3)	C5—H5	0.9300
C9—C10	1.499 (3)	C4—C3	1.377 (3)
C8—C7	1.335 (3)	C4—H4	0.9300
C8—H8	0.9300	N2—C13	1.143 (3)
C1—C2	1.379 (3)	C10—H10A	0.9600
C1—C6	1.398 (3)	C10—H10C	0.9600
C1—Cl1	1.738 (2)	C10—H10B	0.9600
C23—C22	1.498 (3)	C20—C21	1.336 (3)
C23—H23A	0.9600	C20—H20	0.9300
C23—H23C	0.9600	C21—H21	0.9300
C23—H23B	0.9600	C7—H7	0.9300
C22—C21	1.453 (3)	C18—C17	1.370 (3)
N1—C12	1.141 (3)	C18—H18	0.9300
C11—C12	1.430 (3)	C17—C16	1.365 (4)
C11—C13	1.435 (3)	C17—H17	0.9300
C19—C14	1.391 (3)	C2—C3	1.376 (3)
C19—C18	1.409 (3)	C2—H2	0.9300
C19—C20	1.445 (3)	C15—C16	1.372 (4)
C6—C5	1.401 (3)	C15—H15	0.9300
C6—C7	1.454 (3)	C3—H3	0.9300
C26—N4	1.139 (3)	C16—H16	0.9300

C22—C24—C26	121.80 (17)	C6—C5—H5	118.9
C22—C24—C25	122.40 (17)	C5—C4—C3	120.0 (2)
C26—C24—C25	115.80 (17)	C5—C4—H4	120.0
C11—C9—C8	119.85 (17)	C3—C4—H4	120.0
C11—C9—C10	119.80 (18)	C9—C10—H10A	109.5
C8—C9—C10	120.35 (16)	C9—C10—H10C	109.5
C7—C8—C9	124.63 (17)	H10A—C10—H10C	109.5
C7—C8—H8	117.7	C9—C10—H10B	109.5
C9—C8—H8	117.7	H10A—C10—H10B	109.5
C2—C1—C6	122.53 (19)	H10C—C10—H10B	109.5
C2—C1—Cl1	117.46 (16)	C21—C20—C19	126.43 (19)
C6—C1—Cl1	120.01 (15)	C21—C20—H20	116.8
C22—C23—H23A	109.5	C19—C20—H20	116.8
C22—C23—H23C	109.5	C20—C21—C22	124.53 (18)
H23A—C23—H23C	109.5	C20—C21—H21	117.7
C22—C23—H23B	109.5	C22—C21—H21	117.7
H23A—C23—H23B	109.5	C8—C7—C6	126.29 (17)
H23C—C23—H23B	109.5	C8—C7—H7	116.9
C24—C22—C21	120.17 (17)	C6—C7—H7	116.9
C24—C22—C23	119.18 (18)	C17—C18—C19	121.7 (2)
C21—C22—C23	120.64 (17)	C17—C18—H18	119.1
C9—C11—C12	121.86 (18)	C19—C18—H18	119.1
C9—C11—C13	122.42 (18)	C16—C17—C18	120.3 (3)
C12—C11—C13	115.70 (18)	C16—C17—H17	119.9
C14—C19—C18	116.2 (2)	C18—C17—H17	119.9
C14—C19—C20	121.75 (19)	C3—C2—C1	119.5 (2)
C18—C19—C20	122.03 (19)	C3—C2—H2	120.3
C1—C6—C5	115.78 (18)	C1—C2—H2	120.3
C1—C6—C7	122.04 (17)	N2—C13—C11	179.7 (2)
C5—C6—C7	122.18 (17)	C16—C15—C14	119.6 (3)
N4—C26—C24	178.2 (3)	C16—C15—H15	120.2
N1—C12—C11	179.5 (3)	C14—C15—H15	120.2
N3—C25—C24	179.2 (2)	C2—C3—C4	120.0 (2)
C15—C14—C19	121.9 (2)	C2—C3—H3	120.0
C15—C14—Cl2	117.28 (19)	C4—C3—H3	120.0
C19—C14—Cl2	120.77 (17)	C17—C16—C15	120.3 (2)
C4—C5—C6	122.21 (19)	C17—C16—H16	119.9
C4—C5—H5	118.9	C15—C16—H16	119.9

C11—C9—C8—C7	176.58 (19)	C1—C6—C5—C4	0.6 (3)
C10—C9—C8—C7	−3.4 (3)	C7—C6—C5—C4	179.95 (18)
C26—C24—C22—C21	178.43 (18)	C6—C5—C4—C3	−0.3 (3)
C25—C24—C22—C21	−0.8 (3)	C14—C19—C20—C21	178.88 (19)
C26—C24—C22—C23	−0.3 (3)	C18—C19—C20—C21	−2.9 (3)
C25—C24—C22—C23	−179.49 (18)	C19—C20—C21—C22	−179.99 (17)
C8—C9—C11—C12	−179.02 (18)	C24—C22—C21—C20	−179.91 (19)
C10—C9—C11—C12	1.0 (3)	C23—C22—C21—C20	−1.2 (3)
C8—C9—C11—C13	−0.8 (3)	C9—C8—C7—C6	179.82 (17)
C10—C9—C11—C13	179.17 (19)	C1—C6—C7—C8	−174.14 (19)
C2—C1—C6—C5	−0.6 (3)	C5—C6—C7—C8	6.5 (3)
Cl1—C1—C6—C5	179.76 (14)	C14—C19—C18—C17	0.2 (3)
C2—C1—C6—C7	−179.94 (18)	C20—C19—C18—C17	−178.10 (19)
Cl1—C1—C6—C7	0.4 (3)	C19—C18—C17—C16	0.8 (3)
C22—C24—C26—N4	35 (9)	C6—C1—C2—C3	0.2 (3)
C25—C24—C26—N4	−146 (9)	Cl1—C1—C2—C3	179.92 (18)
C9—C11—C12—N1	56 (43)	C9—C11—C13—N2	85 (47)
C13—C11—C12—N1	−122 (43)	C12—C11—C13—N2	−96 (47)
C22—C24—C25—N3	−90 (17)	C19—C14—C15—C16	1.2 (3)
C26—C24—C25—N3	91 (17)	Cl2—C14—C15—C16	−178.09 (19)
C18—C19—C14—C15	−1.2 (3)	C1—C2—C3—C4	0.1 (4)
C20—C19—C14—C15	177.10 (19)	C5—C4—C3—C2	−0.1 (4)
C18—C19—C14—Cl2	178.12 (14)	C18—C17—C16—C15	−0.8 (4)
C20—C19—C14—Cl2	−3.6 (3)	C14—C15—C16—C17	−0.2 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10C···N3ⁱ	0.96	2.62	3.564 (3)	166 (1)

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

Experimental details

Crystal data
Chemical formula	C₁₃H₉ClN₂
M_r	228.67
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	7.7177 (2), 11.0539 (5), 14.7236 (5)
α, β, γ (°)	91.260 (3), 103.992 (3), 106.357 (3)
V (Å³)	1163.99 (7)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.67
Crystal size (mm)	0.35 × 0.32 × 0.30

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 Gemini ultra
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.455, 0.502
No. of measured, independent and observed [I > 2σ(I)] reflections	9739, 4135, 3770
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.140, 1.04
No. of reflections	4135
No. of parameters	291
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.20

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10C···N3ⁱ	0.96	2.62	3.564 (3)	165.6 (7)

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

Acknowledgements

The authors thank the Testing Centre of Sichuan University for the diffraction measurements and are grateful for financial support from China West Normal University (No. 10ZB016).

References

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