{[(1Z)-3-Chloro-1H-isoindol-1-yl­idene]meth­yl}dimethyl­amine

Wang, Z.-Y.; Yu, C.-J.

doi:10.1107/S160053681300500X

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o448

doi:10.1107/S160053681300500X

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{[(1Z)-3-Chloro-1H-isoindol-1-ylidene]methyl}dimethylamine

Zhao-Yun Wang ^a ^* and Chang-Jiang Yu ^a

^aSchool of Chemistry and Material Science, Anhui Normal University, Wuhu, People's Republic of China
^*Correspondence e-mail: shine_zywang@yahoo.com.cn

(Received 11 February 2013; accepted 20 February 2013; online 28 February 2013)

The asymmetric unit of the title compound, C₁₁H₁₁ClN₂, contains two almost-planar independent molecules: the isoindole and dimethylaminomethylene mean planes in the two molecules form dihedral angles of 5.45 (8) and 1.34 (8)°. The crystal packing exhibits no short intermolecular contacts, except for a relatively short Cl⋯Cl distance of 3.4907 (7) Å.

Related literature

For applications of related isoindole derivatives, see: Jiao et al. (2010 ). For details of the synthesis, see: von Doheneck et al. (1969 ). For the crystal structure of the related compound 4,5,6,7-tetrafluoro-1-(N,N-dimethylaminomethylene)-1H-isoindole, see: Uno et al. (2007 ).

Experimental

Crystal data

C₁₁H₁₁ClN₂
M_r = 206.67
Monoclinic, P 2₁ /c
a = 12.1588 (9) Å
b = 10.4087 (8) Å
c = 16.3165 (12) Å
β = 92.720 (1)°
V = 2062.6 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 293 K
0.30 × 0.30 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.908, T_max = 0.937
14393 measured reflections
3628 independent reflections
3175 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.092
S = 1.02
3628 reflections
257 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681300500X/cv5388sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681300500X/cv5388Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681300500X/cv5388Isup3.cml

checkCIF report

Comment top

The title compound, (I), was obtained as an intermediate in our ongoing search (Jiao et al., 2010) for new synthetic routes to boron-dipyrromethene (BODIPY). In (I) (Fig. 1), the bond lengths and angles are normal and correspond to those observed in the related 4,5,6,7-tetrafluoro-1-(N,N-dimethylaminomethylene)-1H-isoindole (Uno et al., 2007). In the crystal structure, there are no short intermolecular contacts, except of relatively short Cl···Cl distance of 3.4907 (7) Å.

Related literature top

For applications of related isoindole derivatives, see: Jiao et al. (2010). For details of the synthesis, see: von Doheneck et al. (1969). For the crystal structure of the related compound 4,5,6,7-tetrafluoro-1-(N,N-dimethylaminomethylene)-1H-isoindole, see: Uno et al. (2007).

Experimental top

The title compound was prepared following the known procedure (von Doheneck et al., 1969). To DMF (2.4 ml, 30 mmol) in 7 ml CH₂Cl₂ was added POCl₃ (2.0 ml, 20 mmol), the reaction mixture was stirred under ice-cold condition for 0.5 h. Then isoindolin-1-one (1 g, 7.5 mmol) in 10 ml CH₂Cl₂ was added. After stirring at 333 k for 3 h, the reaction was monitored by TLC, adjusted pH-value to 8 with saturated potassium carbonate, poured into water (50 ml) and extracted with CH₂Cl₂ (3\30 ml). Organic layers were combined, dried over Na₂SO₄, and evaporated to dryness under vacuum. The desired compound was obtained as powder in 30% (280 mg) from column chromatography.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 top

Fig. 1. Two independent molecules of (I) showing the atomic numbering and 30% probability displacement ellipsoids.

{[(1Z)-3-Chloro-1H-isoindol-1-ylidene]methyl}dimethylamine top

Crystal data top

C₁₁H₁₁ClN₂	F(000) = 864
M_r = 206.67	D_x = 1.331 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9633 reflections
a = 12.1588 (9) Å	θ = 2.3–27.6°
b = 10.4087 (8) Å	µ = 0.33 mm⁻¹
c = 16.3165 (12) Å	T = 293 K
β = 92.720 (1)°	Block, colourless
V = 2062.6 (3) Å³	0.30 × 0.30 × 0.20 mm
Z = 8

Data collection top

Bruker SMART APEX CCD diffractometer	3628 independent reflections
Radiation source: fine-focus sealed tube	3175 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
phi and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→14
T_min = 0.908, T_max = 0.937	k = −12→12
14393 measured reflections	l = −19→19

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.092	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0482P)² + 0.6549P] where P = (F_o² + 2F_c²)/3
3628 reflections	(Δ/σ)_max = 0.001
257 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₁H₁₁ClN₂	V = 2062.6 (3) Å³
M_r = 206.67	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.1588 (9) Å	µ = 0.33 mm⁻¹
b = 10.4087 (8) Å	T = 293 K
c = 16.3165 (12) Å	0.30 × 0.30 × 0.20 mm
β = 92.720 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	3628 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	3175 reflections with I > 2σ(I)
T_min = 0.908, T_max = 0.937	R_int = 0.023
14393 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.02	Δρ_max = 0.22 e Å⁻³
3628 reflections	Δρ_min = −0.25 e Å⁻³
257 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
C1	0.10344 (14)	0.95021 (15)	0.17664 (10)	0.0446 (4)
H1	0.0995	1.0308	0.1520	0.054*
C2	0.09492 (15)	0.93661 (16)	0.25997 (10)	0.0485 (4)
H2	0.0855	1.0090	0.2923	0.058*
C3	0.10025 (14)	0.81523 (16)	0.29649 (10)	0.0462 (4)
H3	0.0948	0.8086	0.3530	0.055*
C4	0.11330 (13)	0.70544 (15)	0.25124 (9)	0.0413 (4)
H4	0.1158	0.6253	0.2764	0.050*
C5	0.12269 (12)	0.71688 (14)	0.16626 (9)	0.0351 (3)
C6	0.11816 (12)	0.83963 (14)	0.13021 (9)	0.0360 (3)
C7	0.13229 (13)	0.81558 (14)	0.04517 (9)	0.0379 (3)
C8	0.13736 (12)	0.62763 (14)	0.09977 (9)	0.0363 (3)
C9	0.14062 (12)	0.49581 (14)	0.10851 (9)	0.0382 (3)
H9	0.1383	0.4670	0.1624	0.046*
C10	0.14543 (16)	0.26882 (15)	0.07727 (12)	0.0540 (4)
H10A	0.1493	0.2628	0.1360	0.081*
H10B	0.2076	0.2257	0.0557	0.081*
H10C	0.0787	0.2292	0.0560	0.081*
C11	0.14694 (16)	0.42637 (17)	−0.03484 (10)	0.0521 (4)
H11A	0.1402	0.5168	−0.0454	0.078*
H11B	0.0862	0.3819	−0.0618	0.078*
H11C	0.2147	0.3955	−0.0554	0.078*
C12	0.59631 (16)	1.03344 (17)	0.23675 (11)	0.0538 (4)
H12	0.6607	1.0464	0.2688	0.065*
C13	0.50202 (19)	1.1010 (2)	0.25156 (13)	0.0660 (5)
H13	0.5023	1.1603	0.2942	0.079*
C14	0.40623 (19)	1.0810 (2)	0.20311 (14)	0.0709 (6)
H14	0.3431	1.1266	0.2149	0.085*
C15	0.40161 (16)	0.9966 (2)	0.13874 (13)	0.0624 (5)
H15	0.3371	0.9864	0.1065	0.075*
C16	0.49652 (14)	0.92593 (16)	0.12242 (10)	0.0478 (4)
C17	0.59264 (14)	0.94515 (15)	0.17246 (10)	0.0448 (4)
C18	0.66982 (13)	0.85782 (16)	0.13977 (10)	0.0434 (4)
C19	0.52280 (14)	0.82944 (16)	0.06357 (10)	0.0471 (4)
C20	0.45005 (15)	0.78325 (18)	0.00284 (11)	0.0528 (4)
H20	0.3807	0.8210	0.0022	0.063*
C21	0.56360 (18)	0.6267 (2)	−0.06552 (14)	0.0758 (6)
H21A	0.6006	0.6639	−0.1105	0.114*
H21B	0.5476	0.5381	−0.0772	0.114*
H21C	0.6100	0.6327	−0.0164	0.114*
C22	0.37124 (18)	0.6668 (2)	−0.11346 (14)	0.0765 (7)
H22A	0.3079	0.7170	−0.1011	0.115*
H22B	0.3533	0.5771	−0.1107	0.115*
H22C	0.3931	0.6873	−0.1677	0.115*
Cl1	0.13909 (4)	0.93494 (4)	−0.02823 (2)	0.05378 (15)
Cl2	0.80400 (4)	0.83930 (5)	0.17864 (3)	0.05637 (15)
N1	0.14301 (11)	0.69544 (12)	0.02584 (8)	0.0394 (3)
N2	0.14649 (11)	0.40346 (12)	0.05304 (8)	0.0425 (3)
N3	0.63250 (11)	0.79025 (14)	0.07737 (8)	0.0470 (3)
N4	0.46144 (13)	0.69555 (17)	−0.05409 (10)	0.0597 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0570 (10)	0.0325 (8)	0.0444 (9)	0.0018 (7)	0.0031 (7)	0.0002 (6)
C2	0.0598 (11)	0.0440 (9)	0.0418 (9)	0.0026 (8)	0.0044 (8)	−0.0093 (7)
C3	0.0534 (10)	0.0532 (10)	0.0322 (8)	−0.0002 (8)	0.0028 (7)	−0.0016 (7)
C4	0.0485 (9)	0.0403 (8)	0.0351 (8)	−0.0013 (7)	0.0000 (7)	0.0056 (6)
C5	0.0352 (8)	0.0344 (7)	0.0356 (8)	−0.0012 (6)	0.0001 (6)	0.0017 (6)
C6	0.0387 (8)	0.0338 (7)	0.0353 (8)	−0.0008 (6)	0.0011 (6)	0.0020 (6)
C7	0.0461 (9)	0.0338 (8)	0.0339 (8)	0.0001 (6)	0.0020 (6)	0.0053 (6)
C8	0.0426 (8)	0.0330 (7)	0.0330 (7)	0.0004 (6)	−0.0005 (6)	0.0029 (6)
C9	0.0422 (8)	0.0359 (8)	0.0363 (8)	0.0003 (6)	−0.0007 (6)	0.0032 (6)
C10	0.0635 (11)	0.0305 (8)	0.0678 (12)	0.0005 (8)	−0.0006 (9)	0.0020 (8)
C11	0.0700 (12)	0.0432 (9)	0.0431 (9)	0.0055 (8)	0.0020 (8)	−0.0062 (7)
C12	0.0610 (11)	0.0499 (10)	0.0507 (10)	0.0000 (8)	0.0022 (8)	−0.0042 (8)
C13	0.0795 (14)	0.0571 (12)	0.0621 (12)	0.0092 (10)	0.0101 (10)	−0.0101 (9)
C14	0.0653 (13)	0.0690 (13)	0.0794 (15)	0.0198 (10)	0.0122 (11)	−0.0055 (11)
C15	0.0512 (11)	0.0667 (12)	0.0692 (12)	0.0101 (9)	0.0008 (9)	−0.0007 (10)
C16	0.0481 (9)	0.0486 (9)	0.0468 (9)	0.0005 (7)	0.0038 (7)	0.0047 (7)
C17	0.0501 (9)	0.0416 (9)	0.0429 (9)	−0.0018 (7)	0.0047 (7)	0.0043 (7)
C18	0.0429 (9)	0.0456 (9)	0.0415 (9)	−0.0034 (7)	0.0004 (7)	0.0006 (7)
C19	0.0431 (9)	0.0531 (10)	0.0450 (9)	−0.0012 (7)	0.0005 (7)	0.0016 (7)
C20	0.0452 (10)	0.0637 (11)	0.0493 (10)	−0.0022 (8)	0.0007 (8)	0.0013 (9)
C21	0.0614 (13)	0.0909 (16)	0.0746 (14)	−0.0004 (11)	−0.0014 (11)	−0.0300 (13)
C22	0.0618 (13)	0.1050 (19)	0.0612 (13)	−0.0195 (12)	−0.0116 (10)	−0.0111 (12)
Cl1	0.0843 (3)	0.0378 (2)	0.0396 (2)	0.00008 (19)	0.0071 (2)	0.01022 (16)
Cl2	0.0481 (3)	0.0647 (3)	0.0553 (3)	0.0043 (2)	−0.00815 (19)	−0.0132 (2)
N1	0.0484 (7)	0.0355 (7)	0.0342 (7)	0.0003 (6)	0.0030 (6)	0.0010 (5)
N2	0.0530 (8)	0.0308 (6)	0.0436 (7)	0.0030 (6)	−0.0001 (6)	0.0003 (6)
N3	0.0453 (8)	0.0512 (8)	0.0445 (8)	−0.0018 (6)	0.0009 (6)	−0.0026 (6)
N4	0.0486 (9)	0.0767 (11)	0.0533 (9)	−0.0088 (8)	−0.0045 (7)	−0.0110 (8)

Geometric parameters (Å, º) top

C1—C2	1.376 (2)	C12—C13	1.376 (3)
C1—C6	1.394 (2)	C12—C17	1.394 (2)
C1—H1	0.9300	C12—H12	0.9300
C2—C3	1.397 (2)	C13—C14	1.392 (3)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.374 (2)	C14—C15	1.368 (3)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.402 (2)	C15—C16	1.405 (3)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.406 (2)	C16—C17	1.408 (2)
C5—C8	1.446 (2)	C16—C19	1.436 (2)
C6—C7	1.428 (2)	C17—C18	1.428 (2)
C7—N1	1.2977 (19)	C18—N3	1.301 (2)
C7—Cl1	1.7303 (14)	C18—Cl2	1.7328 (16)
C8—C9	1.380 (2)	C19—C20	1.383 (2)
C8—N1	1.4021 (19)	C19—N3	1.403 (2)
C9—N2	1.325 (2)	C20—N4	1.314 (2)
C9—H9	0.9300	C20—H20	0.9300
C10—N2	1.456 (2)	C21—N4	1.454 (3)
C10—H10A	0.9600	C21—H21A	0.9600
C10—H10B	0.9600	C21—H21B	0.9600
C10—H10C	0.9600	C21—H21C	0.9600
C11—N2	1.454 (2)	C22—N4	1.460 (2)
C11—H11A	0.9600	C22—H22A	0.9600
C11—H11B	0.9600	C22—H22B	0.9600
C11—H11C	0.9600	C22—H22C	0.9600

C2—C1—C6	118.01 (14)	C12—C13—H13	119.8
C2—C1—H1	121.0	C14—C13—H13	119.8
C6—C1—H1	121.0	C15—C14—C13	122.32 (19)
C1—C2—C3	120.69 (15)	C15—C14—H14	118.8
C1—C2—H2	119.7	C13—C14—H14	118.8
C3—C2—H2	119.7	C14—C15—C16	118.53 (19)
C4—C3—C2	121.82 (15)	C14—C15—H15	120.7
C4—C3—H3	119.1	C16—C15—H15	120.7
C2—C3—H3	119.1	C15—C16—C17	118.84 (17)
C3—C4—C5	118.54 (14)	C15—C16—C19	134.76 (17)
C3—C4—H4	120.7	C17—C16—C19	106.39 (15)
C5—C4—H4	120.7	C12—C17—C16	121.75 (16)
C4—C5—C6	119.17 (14)	C12—C17—C18	134.65 (17)
C4—C5—C8	134.94 (14)	C16—C17—C18	103.60 (14)
C6—C5—C8	105.89 (13)	N3—C18—C17	115.17 (15)
C1—C6—C5	121.76 (14)	N3—C18—Cl2	120.90 (13)
C1—C6—C7	134.18 (14)	C17—C18—Cl2	123.93 (13)
C5—C6—C7	104.06 (13)	C20—C19—N3	125.80 (16)
N1—C7—C6	115.03 (13)	C20—C19—C16	124.55 (16)
N1—C7—Cl1	121.00 (12)	N3—C19—C16	109.65 (14)
C6—C7—Cl1	123.95 (11)	N4—C20—C19	131.49 (18)
C9—C8—N1	125.96 (14)	N4—C20—H20	114.3
C9—C8—C5	124.43 (13)	C19—C20—H20	114.3
N1—C8—C5	109.56 (12)	N4—C21—H21A	109.5
N2—C9—C8	130.78 (14)	N4—C21—H21B	109.5
N2—C9—H9	114.6	H21A—C21—H21B	109.5
C8—C9—H9	114.6	N4—C21—H21C	109.5
N2—C10—H10A	109.5	H21A—C21—H21C	109.5
N2—C10—H10B	109.5	H21B—C21—H21C	109.5
H10A—C10—H10B	109.5	N4—C22—H22A	109.5
N2—C10—H10C	109.5	N4—C22—H22B	109.5
H10A—C10—H10C	109.5	H22A—C22—H22B	109.5
H10B—C10—H10C	109.5	N4—C22—H22C	109.5
N2—C11—H11A	109.5	H22A—C22—H22C	109.5
N2—C11—H11B	109.5	H22B—C22—H22C	109.5
H11A—C11—H11B	109.5	C7—N1—C8	105.46 (12)
N2—C11—H11C	109.5	C9—N2—C11	123.90 (13)
H11A—C11—H11C	109.5	C9—N2—C10	120.76 (14)
H11B—C11—H11C	109.5	C11—N2—C10	115.21 (13)
C13—C12—C17	118.16 (18)	C18—N3—C19	105.19 (14)
C13—C12—H12	120.9	C20—N4—C21	123.54 (16)
C17—C12—H12	120.9	C20—N4—C22	120.70 (18)
C12—C13—C14	120.38 (19)	C21—N4—C22	115.68 (17)

C6—C1—C2—C3	−0.4 (3)	C13—C12—C17—C18	−178.64 (19)
C1—C2—C3—C4	−0.5 (3)	C15—C16—C17—C12	−0.9 (3)
C2—C3—C4—C5	0.7 (3)	C19—C16—C17—C12	179.98 (15)
C3—C4—C5—C6	−0.2 (2)	C15—C16—C17—C18	178.96 (16)
C3—C4—C5—C8	179.67 (17)	C19—C16—C17—C18	−0.17 (17)
C2—C1—C6—C5	1.0 (2)	C12—C17—C18—N3	180.00 (18)
C2—C1—C6—C7	−178.50 (17)	C16—C17—C18—N3	0.18 (19)
C4—C5—C6—C1	−0.7 (2)	C12—C17—C18—Cl2	0.3 (3)
C8—C5—C6—C1	179.44 (14)	C16—C17—C18—Cl2	−179.51 (12)
C4—C5—C6—C7	178.93 (14)	C15—C16—C19—C20	1.2 (3)
C8—C5—C6—C7	−0.97 (16)	C17—C16—C19—C20	−179.85 (17)
C1—C6—C7—N1	−179.57 (17)	C15—C16—C19—N3	−178.8 (2)
C5—C6—C7—N1	0.91 (19)	C17—C16—C19—N3	0.13 (19)
C1—C6—C7—Cl1	2.2 (3)	N3—C19—C20—N4	0.8 (3)
C5—C6—C7—Cl1	−177.28 (12)	C16—C19—C20—N4	−179.20 (19)
C4—C5—C8—C9	3.3 (3)	C6—C7—N1—C8	−0.42 (19)
C6—C5—C8—C9	−176.81 (15)	Cl1—C7—N1—C8	177.84 (11)
C4—C5—C8—N1	−179.07 (16)	C9—C8—N1—C7	177.31 (16)
C6—C5—C8—N1	0.80 (17)	C5—C8—N1—C7	−0.25 (17)
N1—C8—C9—N2	−2.0 (3)	C8—C9—N2—C11	−2.3 (3)
C5—C8—C9—N2	175.21 (15)	C8—C9—N2—C10	−178.06 (16)
C17—C12—C13—C14	−0.1 (3)	C17—C18—N3—C19	−0.11 (19)
C12—C13—C14—C15	−1.2 (4)	Cl2—C18—N3—C19	179.60 (12)
C13—C14—C15—C16	1.4 (3)	C20—C19—N3—C18	179.96 (17)
C14—C15—C16—C17	−0.4 (3)	C16—C19—N3—C18	−0.02 (19)
C14—C15—C16—C19	178.4 (2)	C19—C20—N4—C21	−1.5 (3)
C13—C12—C17—C16	1.2 (3)	C19—C20—N4—C22	−178.1 (2)

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁ClN₂
M_r	206.67
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.1588 (9), 10.4087 (8), 16.3165 (12)
β (°)	92.720 (1)
V (Å³)	2062.6 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.30 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.908, 0.937
No. of measured, independent and observed [I > 2σ(I)] reflections	14393, 3628, 3175
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.092, 1.02
No. of reflections	3628
No. of parameters	257
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.25

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the Research Culture Funds of Anhui Normal University (grant No. 160–721137).

References

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