5-Chloro-1-[(E)-3-(dimethyl­amino)­acrylo­yl]-3-methyl-1H-benzimidazol-2(3H)-one–6-chloro-1-[(E)-3-(dimethyl­amino)­acrylo­yl]-3-methyl-1H-benzimid­azol-2(3H)-one (4/1)

Dardouri, R.; Rodi, Y.K.; Saffon, N.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536811024706

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1853

doi:10.1107/S1600536811024706

Open

access

5-Chloro-1-[(E)-3-(dimethylamino)acryloyl]-3-methyl-1H-benzimidazol-2(3H)-one–6-chloro-1-[(E)-3-(dimethylamino)acryloyl]-3-methyl-1H-benzimidazol-2(3H)-one (4/1)

Rachida Dardouri,^a Yousef Kandri Rodi,^a Natalie Saffon,^b El Mokhtar Essassi ^c and Seik Weng Ng ^d ^*

^aLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fés, Morocco, ^bService Commun Rayons-X FR2599, Université Paul Sabatier Bâtiment 2R1, 118 route de Narbonne, Toulouse, France, ^cLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 22 June 2011; accepted 23 June 2011; online 30 June 2011)

In the reaction of 7-chloro-1,5-benzodiazepine-2,4-dione with N,N-dimethylformamide/dimethylacetal, the diazepine seven-membered ring undergoes a contraction to form the five-membered ring. The reaction yields two isomers the title compound, C₁₃H₁₄ClN₃O₂; the major component has the chlorine-atom substituent in the 5-position of the benzimidazolone ring and the minor component has the chlorine atom in the 6-position. The two isomers form a disordered co-crystal, the chloromethylbenzimidazolone portion of both components are disordered with respect to each other in a 4:1 ratio [the refined ratio is 0.816 (5):0.184 (5)]; the dimethylaminocryloyl substitutent is ordered. The double bond of the dimethylaminoacryloyl substituent has an E configuration.

Related literature

For the structure of the 7-chloro-1,5-benzodiazepine-2,4-dione reactant, see: Mondieig et al. (2007 ).

Experimental

Crystal data

C₁₃H₁₄ClN₃O₂
M_r = 279.72
Orthorhombic, P b c a
a = 7.3145 (2) Å
b = 14.2903 (3) Å
c = 25.1512 (6) Å
V = 2628.96 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.05 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.918, T_max = 0.986
32296 measured reflections
2684 independent reflections
2103 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.204
S = 1.15
2684 reflections
189 parameters
82 restraints
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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/S1600536811024706/xu5248sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024706/xu5248Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811024706/xu5248Isup3.cml

checkCIF report

Comment top

In the reaction of 7-chloro-1,5-benzodiazepine-2,4-dione (Mondieig et al., 2007) with N,N-dimethylformamide/dimethylacetal, the seven-membered ring that is fused with the chlorobenzene ring undergoes a contraction to form five-membered ring, the reaction yielding C₁₃H₁₄ClN₃O₂. The compound is a 4:1 co-crystal whose major component has the chlorine substituent in the 5-position of the benzimidazolone; the minor component has the chlorine in the 6-position (Scheme I, Fig. 1). The crystal structure is better described in terms of nearly 'whole-molecule disorder" (Fig. 2). Interestingly, if the reactant had been unsubstituted 1,5-benzodiazepine-2,4-dione only, the product would have been a single phase only.

Related literature top

For the structure of the 7-chloro-1,5-benzodiazepine-2,4-dione reactant, see: Mondieig et al. (2007).

Experimental top

7-Chloro-1,5-benzodiazepine-2,4-dione (0.2 g. 0.95 mmol) in N,N-dimethylformamide-dimethylacetal (2.25 ml) was heated at 373 K for 4 h. The solid was collected and washed with cold dichloromethane. The brown product was recrystallized from petroleum ether.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 C₁₃H₁₄ClN₃O₂ co-crystal at the 50% probability level; hydrogen atoms are drawn as arbitrary radius. The minor component is not shown.
	Fig. 2. Nearly whole-molecule disorder.

5-Chloro-1-[(E)-3-(dimethylamino)acryloyl]-3-methyl-1H- benzimidazol-2(3H)-one–6-chloro-1-[(E)- 3-(dimethylamino)acryloyl]-3-methyl-1H-benzimidazol-2(3H)-one (4/1) top

Crystal data top

C₁₃H₁₄ClN₃O₂	F(000) = 1168
M_r = 279.72	D_x = 1.413 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 5721 reflections
a = 7.3145 (2) Å	θ = 2.9–26.2°
b = 14.2903 (3) Å	µ = 0.29 mm⁻¹
c = 25.1512 (6) Å	T = 293 K
V = 2628.96 (11) Å³	Plate, brown
Z = 8	0.30 × 0.25 × 0.05 mm

Data collection top

Bruker APEXII diffractometer	2684 independent reflections
Radiation source: fine-focus sealed tube	2103 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ϕ and ω scans	θ_max = 26.4°, θ_min = 4.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
T_min = 0.918, T_max = 0.986	k = −14→17
32296 measured reflections	l = −31→31

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.204	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.092P)² + 3.0624P] where P = (F_o² + 2F_c²)/3
2684 reflections	(Δ/σ)_max = 0.001
189 parameters	Δρ_max = 0.35 e Å⁻³
82 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₁₃H₁₄ClN₃O₂	V = 2628.96 (11) Å³
M_r = 279.72	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.3145 (2) Å	µ = 0.29 mm⁻¹
b = 14.2903 (3) Å	T = 293 K
c = 25.1512 (6) Å	0.30 × 0.25 × 0.05 mm

Data collection top

Bruker APEXII diffractometer	2684 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2103 reflections with I > 2σ(I)
T_min = 0.918, T_max = 0.986	R_int = 0.053
32296 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	82 restraints
wR(F²) = 0.204	H-atom parameters constrained
S = 1.15	Δρ_max = 0.35 e Å⁻³
2684 reflections	Δρ_min = −0.45 e Å⁻³
189 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.52676 (17)	0.77941 (8)	0.11089 (4)	0.0493 (4)	0.816 (5)
O1	0.5389 (12)	0.7581 (9)	0.4050 (3)	0.0492 (11)	0.816 (5)
N1	0.5117 (6)	0.8034 (3)	0.31659 (15)	0.0341 (8)	0.816 (5)
N2	0.6106 (9)	0.6599 (2)	0.33224 (15)	0.0335 (8)	0.816 (5)
C1	0.6049 (4)	0.67203 (15)	0.27723 (8)	0.0252 (8)	0.816 (5)
C2	0.6483 (5)	0.61571 (14)	0.23398 (10)	0.0316 (8)	0.816 (5)
H2	0.6929	0.5555	0.2394	0.038*	0.816 (5)
C3	0.6252 (5)	0.64935 (17)	0.18256 (9)	0.0372 (9)	0.816 (5)
H3	0.6543	0.6117	0.1536	0.045*	0.816 (5)
C4	0.5586 (6)	0.73931 (19)	0.17439 (9)	0.0376 (10)	0.816 (5)
C5	0.5152 (5)	0.79563 (15)	0.21764 (11)	0.0349 (10)	0.816 (5)
H5	0.4706	0.8558	0.2122	0.042*	0.816 (5)
C6	0.5383 (4)	0.76199 (15)	0.26906 (10)	0.0286 (8)	0.816 (5)
C7	0.4443 (8)	0.8980 (3)	0.32573 (18)	0.0418 (12)	0.816 (5)
H7A	0.3302	0.9063	0.3074	0.063*	0.816 (5)
H7B	0.5318	0.9424	0.3126	0.063*	0.816 (5)
H7C	0.4264	0.9076	0.3631	0.063*	0.816 (5)
C8	0.5526 (9)	0.7426 (3)	0.3577 (2)	0.0367 (10)	0.816 (5)
Cl1'	0.6682 (7)	0.6174 (3)	0.13514 (17)	0.0493 (4)	0.184
O1'	0.532 (5)	0.766 (5)	0.4135 (13)	0.0492 (11)	0.184
N1'	0.500 (3)	0.8135 (16)	0.3296 (7)	0.0341 (8)	0.184
N2'	0.609 (4)	0.6657 (9)	0.3400 (7)	0.0335 (8)	0.184
C1'	0.588 (2)	0.6955 (10)	0.2875 (4)	0.0252 (8)	0.184
C2'	0.632 (3)	0.6387 (9)	0.2445 (6)	0.0316 (8)	0.184
H2'	0.6760	0.5785	0.2502	0.038*	0.184 (5)
C3'	0.609 (3)	0.6718 (12)	0.1930 (5)	0.0372 (9)	0.184
C4'	0.542 (3)	0.7617 (13)	0.1845 (5)	0.0376 (10)	0.184
H4'	0.5271	0.7839	0.1500	0.045*	0.184 (5)
C5'	0.499 (3)	0.8186 (9)	0.2275 (7)	0.0349 (10)	0.184
H5'	0.4549	0.8787	0.2218	0.042*	0.184 (5)
C6'	0.5221 (18)	0.7855 (9)	0.2790 (5)	0.0286 (8)	0.184
C7'	0.431 (4)	0.9061 (17)	0.3435 (11)	0.0418 (12)	0.184
H7'A	0.4976	0.9528	0.3241	0.063*	0.184 (5)
H7'B	0.4466	0.9163	0.3810	0.063*	0.184 (5)
H7'C	0.3036	0.9100	0.3347	0.063*	0.184 (5)
C8'	0.548 (3)	0.7466 (13)	0.3669 (11)	0.0367 (10)	0.184
O2	0.6605 (4)	0.50518 (15)	0.32831 (9)	0.0496 (7)
N3	0.7521 (4)	0.4747 (2)	0.48942 (11)	0.0491 (8)
C9	0.6537 (4)	0.5735 (2)	0.35780 (13)	0.0369 (8)
C10	0.6877 (4)	0.5726 (2)	0.41357 (13)	0.0385 (8)
H10	0.6848	0.6278	0.4331	0.046*
C11	0.7244 (5)	0.4893 (2)	0.43769 (13)	0.0419 (8)
H11	0.7309	0.4371	0.4157	0.050*
C12	0.7832 (7)	0.3809 (3)	0.51016 (17)	0.0679 (13)
H12A	0.7952	0.3377	0.4811	0.102*
H12B	0.6816	0.3627	0.5320	0.102*
H12C	0.8931	0.3803	0.5310	0.102*
C13	0.7423 (6)	0.5493 (3)	0.52792 (14)	0.0616 (11)
H13A	0.6539	0.5948	0.5165	0.092*
H13B	0.8599	0.5786	0.5311	0.092*
H13C	0.7064	0.5243	0.5618	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0640 (7)	0.0447 (6)	0.0391 (6)	−0.0008 (5)	0.0014 (5)	0.0036 (4)
O1	0.0615 (18)	0.041 (3)	0.045 (3)	0.0082 (17)	0.0003 (18)	−0.012 (2)
N1	0.0370 (16)	0.0230 (17)	0.042 (2)	0.0014 (12)	0.0022 (15)	−0.0035 (15)
N2	0.0343 (14)	0.0272 (13)	0.0391 (18)	−0.0006 (12)	−0.0039 (15)	−0.0031 (12)
C1	0.0230 (15)	0.0169 (17)	0.0357 (18)	−0.0020 (14)	0.0010 (14)	−0.0065 (14)
C2	0.0322 (18)	0.0241 (19)	0.039 (2)	−0.0012 (16)	−0.0007 (16)	−0.0060 (14)
C3	0.038 (2)	0.036 (2)	0.038 (2)	−0.0052 (18)	0.0046 (17)	−0.0077 (16)
C4	0.037 (2)	0.038 (3)	0.038 (2)	−0.0075 (19)	0.0018 (17)	−0.0005 (16)
C5	0.0281 (18)	0.0218 (19)	0.055 (3)	−0.0007 (16)	−0.0005 (17)	0.0045 (18)
C6	0.0223 (16)	0.016 (2)	0.047 (2)	−0.0009 (15)	0.0009 (14)	−0.0027 (14)
C7	0.049 (2)	0.0284 (18)	0.048 (3)	0.0036 (16)	0.003 (2)	−0.008 (2)
C8	0.0359 (18)	0.0306 (16)	0.044 (3)	0.0020 (14)	−0.0027 (18)	−0.0055 (16)
Cl1'	0.0640 (7)	0.0447 (6)	0.0391 (6)	−0.0008 (5)	0.0014 (5)	0.0036 (4)
O1'	0.0615 (18)	0.041 (3)	0.045 (3)	0.0082 (17)	0.0003 (18)	−0.012 (2)
N1'	0.0370 (16)	0.0230 (17)	0.042 (2)	0.0014 (12)	0.0022 (15)	−0.0035 (15)
N2'	0.0343 (14)	0.0272 (13)	0.0391 (18)	−0.0006 (12)	−0.0039 (15)	−0.0031 (12)
C1'	0.0230 (15)	0.0169 (17)	0.0357 (18)	−0.0020 (14)	0.0010 (14)	−0.0065 (14)
C2'	0.0322 (18)	0.0241 (19)	0.039 (2)	−0.0012 (16)	−0.0007 (16)	−0.0060 (14)
C3'	0.038 (2)	0.036 (2)	0.038 (2)	−0.0052 (18)	0.0046 (17)	−0.0077 (16)
C4'	0.037 (2)	0.038 (3)	0.038 (2)	−0.0075 (19)	0.0018 (17)	−0.0005 (16)
C5'	0.0281 (18)	0.0218 (19)	0.055 (3)	−0.0007 (16)	−0.0005 (17)	0.0045 (18)
C6'	0.0223 (16)	0.016 (2)	0.047 (2)	−0.0009 (15)	0.0009 (14)	−0.0027 (14)
C7'	0.049 (2)	0.0284 (18)	0.048 (3)	0.0036 (16)	0.003 (2)	−0.008 (2)
C8'	0.0359 (18)	0.0306 (16)	0.044 (3)	0.0020 (14)	−0.0027 (18)	−0.0055 (16)
O2	0.0705 (18)	0.0299 (12)	0.0483 (14)	0.0076 (12)	−0.0090 (12)	−0.0024 (10)
N3	0.0491 (18)	0.0548 (19)	0.0433 (16)	0.0079 (15)	0.0003 (14)	0.0081 (13)
C9	0.0320 (17)	0.0316 (16)	0.0470 (18)	0.0005 (13)	−0.0020 (13)	0.0020 (14)
C10	0.0364 (17)	0.0352 (16)	0.0439 (17)	0.0012 (14)	−0.0004 (14)	−0.0024 (14)
C11	0.0386 (19)	0.0417 (18)	0.0453 (18)	0.0013 (15)	−0.0004 (14)	0.0015 (14)
C12	0.071 (3)	0.074 (3)	0.059 (2)	0.018 (2)	0.011 (2)	0.029 (2)
C13	0.063 (3)	0.080 (3)	0.0422 (19)	−0.003 (2)	−0.0037 (19)	−0.0049 (19)

Geometric parameters (Å, º) top

Cl1—C4	1.713 (2)	N2'—C9	1.430 (9)
O1—C8	1.213 (5)	C1'—C2'	1.3900
N1—C6	1.348 (3)	C1'—C6'	1.3900
N1—C8	1.383 (5)	C2'—C3'	1.3900
N1—C7	1.458 (5)	C2'—H2'	0.9300
N2—C1	1.395 (3)	C3'—C4'	1.3900
N2—C8	1.409 (4)	C4'—C5'	1.3900
N2—C9	1.427 (4)	C4'—H4'	0.9300
C1—C2	1.3900	C5'—C6'	1.3900
C1—C6	1.3900	C5'—H5'	0.9300
C2—C3	1.3900	C7'—H7'A	0.9600
C2—H2	0.9300	C7'—H7'B	0.9600
C3—C4	1.3900	C7'—H7'C	0.9600
C3—H3	0.9300	O2—C9	1.227 (4)
C4—C5	1.3900	N3—C11	1.333 (4)
C5—C6	1.3900	N3—C13	1.442 (5)
C5—H5	0.9300	N3—C12	1.457 (5)
C7—H7A	0.9600	C9—C10	1.424 (5)
C7—H7B	0.9600	C10—C11	1.363 (5)
C7—H7C	0.9600	C10—H10	0.9300
Cl1'—C3'	1.705 (8)	C11—H11	0.9300
O1'—C8'	1.213 (10)	C12—H12A	0.9600
N1'—C6'	1.343 (10)	C12—H12B	0.9600
N1'—C8'	1.385 (10)	C12—H12C	0.9600
N1'—C7'	1.458 (10)	C13—H13A	0.9600
N2'—C1'	1.395 (9)	C13—H13B	0.9600
N2'—C8'	1.410 (10)	C13—H13C	0.9600

C6—N1—C8	110.9 (4)	C5'—C4'—H4'	120.0
C6—N1—C7	126.6 (4)	C3'—C4'—H4'	120.0
C8—N1—C7	122.5 (3)	C4'—C5'—C6'	120.0
C1—N2—C8	109.7 (3)	C4'—C5'—H5'	120.0
C1—N2—C9	124.1 (3)	C6'—C5'—H5'	120.0
C8—N2—C9	125.9 (4)	N1'—C6'—C5'	140.1 (15)
C2—C1—C6	120.0	N1'—C6'—C1'	99.9 (15)
C2—C1—N2	134.2 (2)	C5'—C6'—C1'	120.0
C6—C1—N2	105.8 (2)	N1'—C7'—H7'A	109.5
C3—C2—C1	120.0	N1'—C7'—H7'B	109.5
C3—C2—H2	120.0	H7'A—C7'—H7'B	109.5
C1—C2—H2	120.0	N1'—C7'—H7'C	109.5
C4—C3—C2	120.0	H7'A—C7'—H7'C	109.5
C4—C3—H3	120.0	H7'B—C7'—H7'C	109.5
C2—C3—H3	120.0	O1'—C8'—N1'	118 (4)
C5—C4—C3	120.0	O1'—C8'—N2'	133 (4)
C5—C4—Cl1	120.32 (15)	N1'—C8'—N2'	109 (2)
C3—C4—Cl1	119.67 (15)	C11—N3—C13	122.1 (3)
C4—C5—C6	120.0	C11—N3—C12	121.2 (3)
C4—C5—H5	120.0	C13—N3—C12	116.6 (3)
C6—C5—H5	120.0	O2—C9—C10	125.5 (3)
N1—C6—C5	131.0 (3)	O2—C9—N2	115.1 (3)
N1—C6—C1	109.0 (3)	C10—C9—N2	119.3 (3)
C5—C6—C1	120.0	O2—C9—N2'	123.6 (8)
O1—C8—N1	126.9 (8)	C10—C9—N2'	110.9 (8)
O1—C8—N2	128.5 (8)	C11—C10—C9	118.7 (3)
N1—C8—N2	104.6 (4)	C11—C10—H10	120.6
C6'—N1'—C8'	114 (2)	C9—C10—H10	120.6
C6'—N1'—C7'	122.7 (19)	N3—C11—C10	127.0 (3)
C8'—N1'—C7'	123.5 (16)	N3—C11—H11	116.5
C1'—N2'—C8'	99.7 (15)	C10—C11—H11	116.5
C1'—N2'—C9	127.0 (15)	N3—C12—H12A	109.5
C8'—N2'—C9	132.6 (15)	N3—C12—H12B	109.5
C2'—C1'—C6'	120.0	H12A—C12—H12B	109.5
C2'—C1'—N2'	122.3 (12)	N3—C12—H12C	109.5
C6'—C1'—N2'	117.7 (12)	H12A—C12—H12C	109.5
C1'—C2'—C3'	120.0	H12B—C12—H12C	109.5
C1'—C2'—H2'	120.0	N3—C13—H13A	109.5
C3'—C2'—H2'	120.0	N3—C13—H13B	109.5
C2'—C3'—C4'	120.0	H13A—C13—H13B	109.5
C2'—C3'—Cl1'	127.5 (11)	N3—C13—H13C	109.5
C4'—C3'—Cl1'	112.3 (11)	H13A—C13—H13C	109.5
C5'—C4'—C3'	120.0	H13B—C13—H13C	109.5

C8—N2—C1—C2	178.9 (2)	Cl1'—C3'—C4'—C5'	−175.6 (11)
C9—N2—C1—C2	−6.1 (7)	C3'—C4'—C5'—C6'	0.0
C8—N2—C1—C6	−1.5 (3)	C8'—N1'—C6'—C5'	180.0 (3)
C9—N2—C1—C6	173.4 (5)	C7'—N1'—C6'—C5'	0.1 (8)
C6—C1—C2—C3	0.0	C8'—N1'—C6'—C1'	−0.1 (5)
N2—C1—C2—C3	179.5 (3)	C7'—N1'—C6'—C1'	−180.0 (5)
C1—C2—C3—C4	0.0	C4'—C5'—C6'—N1'	180.0 (4)
C2—C3—C4—C5	0.0	C4'—C5'—C6'—C1'	0.0
C2—C3—C4—Cl1	−178.8 (3)	C2'—C1'—C6'—N1'	−180.0 (3)
C3—C4—C5—C6	0.0	N2'—C1'—C6'—N1'	0.0 (4)
Cl1—C4—C5—C6	178.8 (3)	C2'—C1'—C6'—C5'	0.0
C8—N1—C6—C5	180.0 (2)	N2'—C1'—C6'—C5'	−180.0 (3)
C7—N1—C6—C5	1.7 (5)	C6'—N1'—C8'—O1'	−180.0 (6)
C8—N1—C6—C1	−2.1 (3)	C7'—N1'—C8'—O1'	−0.1 (10)
C7—N1—C6—C1	179.6 (3)	C6'—N1'—C8'—N2'	0.1 (7)
C4—C5—C6—N1	177.7 (3)	C7'—N1'—C8'—N2'	180.0 (6)
C4—C5—C6—C1	0.0	C1'—N2'—C8'—O1'	−180.0 (7)
C2—C1—C6—N1	−178.2 (2)	C9—N2'—C8'—O1'	9 (3)
N2—C1—C6—N1	2.2 (3)	C1'—N2'—C8'—N1'	0.0 (6)
C2—C1—C6—C5	0.0	C9—N2'—C8'—N1'	−172 (2)
N2—C1—C6—C5	−179.6 (2)	C1—N2—C9—O2	−10.2 (7)
C6—N1—C8—O1	−178.3 (4)	C8—N2—C9—O2	164.0 (4)
C7—N1—C8—O1	0.1 (7)	C1—N2—C9—C10	168.9 (4)
C6—N1—C8—N2	1.1 (4)	C8—N2—C9—C10	−17.0 (6)
C7—N1—C8—N2	179.5 (4)	C1—N2—C9—N2'	178 (9)
C1—N2—C8—O1	179.7 (4)	C8—N2—C9—N2'	−8 (9)
C9—N2—C8—O1	4.8 (8)	C1'—N2'—C9—O2	−8 (2)
C1—N2—C8—N1	0.3 (4)	C8'—N2'—C9—O2	161.0 (11)
C9—N2—C8—N1	−174.5 (5)	C1'—N2'—C9—C10	171.9 (12)
C8'—N2'—C1'—C2'	−180.0 (3)	C8'—N2'—C9—C10	−19 (2)
C9—N2'—C1'—C2'	−8 (2)	C1'—N2'—C9—N2	0 (7)
C8'—N2'—C1'—C6'	0.0 (5)	C8'—N2'—C9—N2	170 (10)
C9—N2'—C1'—C6'	172 (2)	O2—C9—C10—C11	−2.6 (5)
C6'—C1'—C2'—C3'	0.0	N2—C9—C10—C11	178.5 (4)
N2'—C1'—C2'—C3'	180.0 (3)	N2'—C9—C10—C11	177.1 (12)
C1'—C2'—C3'—C4'	0.0	C13—N3—C11—C10	1.3 (6)
C1'—C2'—C3'—Cl1'	174.9 (13)	C12—N3—C11—C10	177.6 (4)
C2'—C3'—C4'—C5'	0.0	C9—C10—C11—N3	−177.1 (3)

Experimental details

Crystal data
Chemical formula	C₁₃H₁₄ClN₃O₂
M_r	279.72
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	7.3145 (2), 14.2903 (3), 25.1512 (6)
V (Å³)	2628.96 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.30 × 0.25 × 0.05

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.918, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	32296, 2684, 2103
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.204, 1.15
No. of reflections	2684
No. of parameters	189
No. of restraints	82
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.45

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank Université Sidi Mohamed Ben Abdallah,Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Mondieig, D., Negrier, Ph., Leger, J. M., Massip, S., Benali, B., Lazar, Z., Boucetta, A., Lakhrissi, B. & Massoui, M. (2007). Anal. Sci. X-ray Struct. Anal. Online, 23, x125–x126. CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.