3-{[3-(4-Chloro­phen­yl)-4,5-dihydro-1,2-oxazol-5-yl]meth­yl}-1,5-dimethyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

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

doi:10.1107/S160053681100657X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o720

doi:10.1107/S160053681100657X

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3-{[3-(4-Chlorophenyl)-4,5-dihydro-1,2-oxazol-5-yl]methyl}-1,5-dimethyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Rachida Dardouri,^a Youssef Kandri Rodi,^a Sonia Ladeira,^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 20 February 2011; accepted 21 February 2011; online 26 February 2011)

The seven-membered ring of the title molecule, C₂₁H₂₀ClN₃O₃, adopts a boat-shaped conformation (with the C atoms of the fused-ring as the stern and the methine C atom as the prow). The substituent at the 3-position occupies an equatorial position; its five-membered ring is approximately planar (r.m.s. deviation = 0.081 Å), and is aligned at 14.5 (1)° with respect to the chlorophenyl ring to which it is connected.

Related literature

For the crystal structure of the tetradecyl-substituted analog, see: Dardouri et al. (2011 ).

Experimental

Crystal data

C₂₁H₂₀ClN₃O₃
M_r = 397.85
Triclinic, $[P \overline 1]$
a = 8.1821 (1) Å
b = 9.0741 (1) Å
c = 13.3792 (2) Å
α = 79.748 (1)°
β = 80.142 (1)°
γ = 85.910 (1)°
V = 962.19 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 295 K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker X8 APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.915, T_max = 0.956
19243 measured reflections
4383 independent reflections
4056 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.184
S = 1.03
4383 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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/S160053681100657X/bt5479sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681100657X/bt5479Isup2.hkl

checkCIF report

Comment top

The methylene part of 1,5-dimethyl-1,5-benzodiazepine-2,4-dione is relatively acidic, and one proton can be abstracted by using potassium t-butoxide; the resulting carbanion can undergo a nucleophlilic subsitution with a dibromoalkane to form 3-substituted derivatives. In a previous study, the compound was reacted with bromotetradecane to give the tetradecyl substitued derivative (Dardouri et al., 2011). The title compound was obtained by using p-chlorobenzaldoxime to react with the ally group to furnish the title isoxazolinyl derivative (Scheme I, Fig. 1). The seven-membered ring of C₂₁H₂₀ClN₃O₃ adopts a boat-shaped conformation (with the C atoms of the fused-ring as the stern and the methine C atom as the prow). The substituent at the 3-position occupies an equatorial position.

Related literature top

For the crystal structure of the tetradecyl-substituted analog, see: Dardouri et al. (2011).

Experimental top

To a solution of 3-allyl-1,5-dimethyl-1,5-benzodiazepine-2,4-dione (0.25 g, 1 mmol) and p-chlorobenzaldoxime (0.2 g, 1.3 mmol) in chloroform (10 ml) was added to a 4%solution of sodium hypochlorite solution (commerical bleach) (4 ml) at 273 K. Stirring was continued for 4 h. The organic layer was dried and the solvent evaporated under reduced pressure. The residue was then purified by column chromatography on silica gel by using a mixture of hexane and ethyl acetate (1/1) as eluent. Colorless crystals were isolated when the solvent was allowed to evaporate.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₂₁H₂₀ClN₃O₃ at the 50% probability level; hydrogen atoms are drawn as arbitrary radius.

3-{[3-(4-Chlorophenyl)-4,5-dihydro-1,2-oxazol-5-yl]methyl}-1,5-dimethyl- 1H-1,5-benzodiazepine-2,4(3H,5H)-dione top

Crystal data top

C₂₁H₂₀ClN₃O₃	Z = 2
M_r = 397.85	F(000) = 416
Triclinic, P1	D_x = 1.373 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1821 (1) Å	Cell parameters from 9887 reflections
b = 9.0741 (1) Å	θ = 3.0–30.7°
c = 13.3792 (2) Å	µ = 0.23 mm⁻¹
α = 79.748 (1)°	T = 295 K
β = 80.142 (1)°	Block, colorless
γ = 85.910 (1)°	0.40 × 0.30 × 0.20 mm
V = 962.19 (2) Å³

Data collection top

Bruker X8 APEXII diffractometer	4383 independent reflections
Radiation source: fine-focus sealed tube	4056 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.915, T_max = 0.956	k = −11→11
19243 measured reflections	l = −17→17

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)] = 0.066	H-atom parameters constrained
wR(F²) = 0.184	w = 1/[σ²(F_o²) + (0.1062P)² + 0.889P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4383 reflections	Δρ_max = 0.83 e Å⁻³
256 parameters	Δρ_min = −0.44 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.046 (8)

Crystal data top

C₂₁H₂₀ClN₃O₃	γ = 85.910 (1)°
M_r = 397.85	V = 962.19 (2) Å³
Triclinic, P1	Z = 2
a = 8.1821 (1) Å	Mo Kα radiation
b = 9.0741 (1) Å	µ = 0.23 mm⁻¹
c = 13.3792 (2) Å	T = 295 K
α = 79.748 (1)°	0.40 × 0.30 × 0.20 mm
β = 80.142 (1)°

Data collection top

Bruker X8 APEXII diffractometer	4383 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4056 reflections with I > 2σ(I)
T_min = 0.915, T_max = 0.956	R_int = 0.020
19243 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.184	H-atom parameters constrained
S = 1.03	Δρ_max = 0.83 e Å⁻³
4383 reflections	Δρ_min = −0.44 e Å⁻³
256 parameters

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

	x	y	z	U_iso*/U_eq
Cl1	0.00333 (8)	0.14321 (7)	1.07254 (5)	0.0471 (2)
O1	0.2880 (2)	1.2329 (2)	0.66476 (13)	0.0428 (4)
O2	0.6469 (2)	1.2468 (2)	0.82002 (12)	0.0430 (4)
O3	0.6108 (2)	0.79540 (18)	0.76659 (12)	0.0400 (4)
N1	0.5122 (2)	1.2697 (2)	0.53908 (14)	0.0337 (4)
N2	0.7763 (2)	1.2907 (2)	0.65440 (13)	0.0310 (4)
N3	0.5112 (2)	0.6671 (2)	0.78978 (14)	0.0353 (4)
C1	0.6816 (3)	1.2379 (2)	0.50002 (15)	0.0309 (4)
C2	0.7216 (3)	1.2001 (3)	0.40171 (18)	0.0452 (6)
H2	0.6374	1.1910	0.3647	0.054*
C3	0.8856 (4)	1.1760 (4)	0.35894 (19)	0.0504 (7)
H3	0.9109	1.1522	0.2931	0.060*
C4	1.0116 (3)	1.1870 (3)	0.4132 (2)	0.0448 (6)
H4	1.1216	1.1710	0.3839	0.054*
C5	0.9744 (3)	1.2219 (3)	0.51136 (18)	0.0360 (5)
H5	1.0596	1.2275	0.5483	0.043*
C6	0.8100 (3)	1.2487 (2)	0.55536 (15)	0.0284 (4)
C7	0.4069 (3)	1.3563 (3)	0.46807 (19)	0.0449 (6)
H7A	0.3220	1.4127	0.5059	0.067*
H7B	0.3563	1.2889	0.4359	0.067*
H7C	0.4739	1.4237	0.4163	0.067*
C8	0.4365 (3)	1.2097 (2)	0.63486 (16)	0.0313 (4)
C9	0.5486 (3)	1.1145 (2)	0.70220 (15)	0.0293 (4)
H9	0.6178	1.0465	0.6616	0.035*
C10	0.6618 (3)	1.2213 (2)	0.73248 (15)	0.0301 (4)
C11	0.8826 (3)	1.3976 (3)	0.6799 (2)	0.0437 (6)
H11A	0.8160	1.4626	0.7216	0.065*
H11B	0.9365	1.4563	0.6177	0.065*
H11C	0.9648	1.3438	0.7173	0.065*
C12	0.4489 (3)	1.0212 (2)	0.79575 (16)	0.0307 (4)
H12A	0.4059	1.0846	0.8463	0.037*
H12B	0.3551	0.9814	0.7752	0.037*
C13	0.5550 (3)	0.8928 (2)	0.84372 (16)	0.0326 (4)
H13	0.6499	0.9304	0.8659	0.039*
C14	0.4547 (3)	0.7892 (2)	0.93283 (15)	0.0317 (4)
H14A	0.5181	0.7544	0.9881	0.038*
H14B	0.3515	0.8382	0.9599	0.038*
C15	0.4243 (3)	0.6634 (2)	0.87944 (15)	0.0301 (4)
C16	0.3142 (2)	0.5391 (2)	0.92464 (15)	0.0290 (4)
C17	0.2745 (3)	0.4381 (3)	0.86525 (16)	0.0352 (5)
H17	0.3144	0.4520	0.7950	0.042*
C18	0.1772 (3)	0.3186 (3)	0.90967 (18)	0.0367 (5)
H18	0.1508	0.2523	0.8698	0.044*
C19	0.1190 (3)	0.2982 (2)	1.01501 (17)	0.0330 (4)
C20	0.1526 (3)	0.3979 (2)	1.07529 (16)	0.0310 (4)
H20	0.1109	0.3840	1.1453	0.037*
C21	0.2496 (3)	0.5188 (2)	1.02965 (15)	0.0291 (4)
H21	0.2718	0.5871	1.0693	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0506 (4)	0.0392 (3)	0.0554 (4)	−0.0106 (2)	−0.0094 (3)	−0.0145 (3)
O1	0.0328 (8)	0.0558 (11)	0.0374 (9)	0.0037 (7)	−0.0019 (6)	−0.0071 (7)
O2	0.0561 (10)	0.0510 (10)	0.0238 (7)	−0.0044 (8)	−0.0058 (7)	−0.0114 (7)
O3	0.0490 (9)	0.0360 (8)	0.0274 (7)	0.0054 (7)	0.0083 (6)	−0.0011 (6)
N1	0.0331 (9)	0.0421 (10)	0.0258 (8)	−0.0033 (7)	−0.0058 (7)	−0.0037 (7)
N2	0.0381 (9)	0.0322 (9)	0.0248 (8)	−0.0041 (7)	−0.0079 (7)	−0.0063 (7)
N3	0.0432 (10)	0.0348 (9)	0.0241 (8)	0.0085 (8)	−0.0014 (7)	−0.0026 (7)
C1	0.0339 (10)	0.0360 (10)	0.0220 (9)	−0.0061 (8)	−0.0025 (7)	−0.0030 (7)
C2	0.0481 (13)	0.0640 (16)	0.0256 (10)	−0.0096 (11)	−0.0045 (9)	−0.0121 (10)
C3	0.0542 (15)	0.0698 (18)	0.0267 (11)	−0.0104 (13)	0.0074 (10)	−0.0166 (11)
C4	0.0384 (12)	0.0523 (14)	0.0400 (12)	−0.0074 (10)	0.0093 (10)	−0.0104 (11)
C5	0.0338 (11)	0.0379 (11)	0.0356 (11)	−0.0038 (8)	−0.0045 (8)	−0.0042 (9)
C6	0.0346 (10)	0.0284 (9)	0.0214 (9)	−0.0045 (7)	−0.0037 (7)	−0.0018 (7)
C7	0.0408 (12)	0.0581 (15)	0.0366 (12)	−0.0014 (11)	−0.0149 (10)	−0.0020 (11)
C8	0.0338 (10)	0.0339 (10)	0.0271 (10)	−0.0031 (8)	−0.0027 (8)	−0.0091 (8)
C9	0.0326 (10)	0.0301 (9)	0.0235 (9)	−0.0002 (7)	−0.0005 (7)	−0.0045 (7)
C10	0.0370 (10)	0.0306 (10)	0.0224 (9)	0.0026 (8)	−0.0059 (7)	−0.0042 (7)
C11	0.0472 (13)	0.0469 (13)	0.0433 (13)	−0.0099 (10)	−0.0154 (10)	−0.0137 (10)
C12	0.0292 (9)	0.0346 (10)	0.0267 (9)	−0.0003 (8)	−0.0023 (7)	−0.0030 (8)
C13	0.0309 (10)	0.0381 (11)	0.0263 (9)	0.0005 (8)	−0.0025 (7)	−0.0016 (8)
C14	0.0391 (11)	0.0322 (10)	0.0211 (9)	−0.0001 (8)	−0.0008 (8)	−0.0015 (7)
C15	0.0358 (10)	0.0327 (10)	0.0202 (8)	0.0085 (8)	−0.0057 (7)	−0.0033 (7)
C16	0.0311 (10)	0.0328 (10)	0.0237 (9)	0.0069 (8)	−0.0067 (7)	−0.0075 (7)
C17	0.0383 (11)	0.0450 (12)	0.0250 (9)	0.0090 (9)	−0.0086 (8)	−0.0145 (8)
C18	0.0383 (11)	0.0415 (12)	0.0374 (11)	0.0085 (9)	−0.0143 (9)	−0.0216 (9)
C19	0.0306 (10)	0.0337 (10)	0.0376 (11)	0.0033 (8)	−0.0095 (8)	−0.0116 (8)
C20	0.0337 (10)	0.0336 (10)	0.0267 (9)	0.0002 (8)	−0.0044 (8)	−0.0094 (8)
C21	0.0349 (10)	0.0304 (10)	0.0231 (9)	0.0029 (8)	−0.0056 (7)	−0.0085 (7)

Geometric parameters (Å, º) top

Cl1—C19	1.738 (2)	C9—C12	1.523 (3)
O1—C8	1.228 (3)	C9—C10	1.536 (3)
O2—C10	1.218 (3)	C9—H9	0.9800
O3—N3	1.427 (3)	C11—H11A	0.9600
O3—C13	1.470 (3)	C11—H11B	0.9600
N1—C8	1.360 (3)	C11—H11C	0.9600
N1—C1	1.423 (3)	C12—C13	1.518 (3)
N1—C7	1.477 (3)	C12—H12A	0.9700
N2—C10	1.371 (3)	C12—H12B	0.9700
N2—C6	1.420 (3)	C13—C14	1.534 (3)
N2—C11	1.467 (3)	C13—H13	0.9800
N3—C15	1.282 (3)	C14—C15	1.506 (3)
C1—C2	1.397 (3)	C14—H14A	0.9700
C1—C6	1.403 (3)	C14—H14B	0.9700
C2—C3	1.384 (4)	C15—C16	1.471 (3)
C2—H2	0.9300	C16—C21	1.398 (3)
C3—C4	1.378 (4)	C16—C17	1.403 (3)
C3—H3	0.9300	C17—C18	1.376 (4)
C4—C5	1.383 (3)	C17—H17	0.9300
C4—H4	0.9300	C18—C19	1.392 (3)
C5—C6	1.396 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.384 (3)
C7—H7A	0.9600	C20—C21	1.388 (3)
C7—H7B	0.9600	C20—H20	0.9300
C7—H7C	0.9600	C21—H21	0.9300
C8—C9	1.514 (3)

N3—O3—C13	109.02 (15)	N2—C11—H11B	109.5
C8—N1—C1	123.46 (18)	H11A—C11—H11B	109.5
C8—N1—C7	117.58 (19)	N2—C11—H11C	109.5
C1—N1—C7	118.47 (18)	H11A—C11—H11C	109.5
C10—N2—C6	122.62 (17)	H11B—C11—H11C	109.5
C10—N2—C11	117.51 (18)	C13—C12—C9	111.22 (17)
C6—N2—C11	119.31 (18)	C13—C12—H12A	109.4
C15—N3—O3	109.03 (18)	C9—C12—H12A	109.4
C2—C1—C6	119.0 (2)	C13—C12—H12B	109.4
C2—C1—N1	118.8 (2)	C9—C12—H12B	109.4
C6—C1—N1	122.17 (18)	H12A—C12—H12B	108.0
C3—C2—C1	120.5 (2)	O3—C13—C12	107.78 (17)
C3—C2—H2	119.8	O3—C13—C14	103.57 (17)
C1—C2—H2	119.8	C12—C13—C14	112.48 (17)
C4—C3—C2	120.5 (2)	O3—C13—H13	110.9
C4—C3—H3	119.8	C12—C13—H13	110.9
C2—C3—H3	119.8	C14—C13—H13	110.9
C3—C4—C5	119.9 (2)	C15—C14—C13	100.88 (16)
C3—C4—H4	120.0	C15—C14—H14A	111.6
C5—C4—H4	120.0	C13—C14—H14A	111.6
C4—C5—C6	120.5 (2)	C15—C14—H14B	111.6
C4—C5—H5	119.7	C13—C14—H14B	111.6
C6—C5—H5	119.7	H14A—C14—H14B	109.4
C5—C6—C1	119.58 (19)	N3—C15—C16	120.6 (2)
C5—C6—N2	119.19 (19)	N3—C15—C14	114.1 (2)
C1—C6—N2	121.20 (18)	C16—C15—C14	125.22 (17)
N1—C7—H7A	109.5	C21—C16—C17	118.9 (2)
N1—C7—H7B	109.5	C21—C16—C15	119.55 (19)
H7A—C7—H7B	109.5	C17—C16—C15	121.59 (19)
N1—C7—H7C	109.5	C18—C17—C16	120.8 (2)
H7A—C7—H7C	109.5	C18—C17—H17	119.6
H7B—C7—H7C	109.5	C16—C17—H17	119.6
O1—C8—N1	122.1 (2)	C17—C18—C19	119.1 (2)
O1—C8—C9	122.53 (19)	C17—C18—H18	120.4
N1—C8—C9	115.32 (18)	C19—C18—H18	120.4
C8—C9—C12	111.58 (17)	C20—C19—C18	121.4 (2)
C8—C9—C10	107.09 (17)	C20—C19—Cl1	119.19 (17)
C12—C9—C10	112.23 (17)	C18—C19—Cl1	119.38 (17)
C8—C9—H9	108.6	C21—C20—C19	119.01 (19)
C12—C9—H9	108.6	C21—C20—H20	120.5
C10—C9—H9	108.6	C19—C20—H20	120.5
O2—C10—N2	122.0 (2)	C20—C21—C16	120.69 (19)
O2—C10—C9	121.92 (19)	C20—C21—H21	119.7
N2—C10—C9	116.09 (17)	C16—C21—H21	119.7
N2—C11—H11A	109.5

C13—O3—N3—C15	−11.1 (2)	C11—N2—C10—C9	177.93 (19)
C8—N1—C1—C2	132.2 (2)	C8—C9—C10—O2	109.6 (2)
C7—N1—C1—C2	−39.5 (3)	C12—C9—C10—O2	−13.1 (3)
C8—N1—C1—C6	−50.2 (3)	C8—C9—C10—N2	−68.0 (2)
C7—N1—C1—C6	138.0 (2)	C12—C9—C10—N2	169.27 (17)
C6—C1—C2—C3	−1.0 (4)	C8—C9—C12—C13	162.03 (18)
N1—C1—C2—C3	176.6 (2)	C10—C9—C12—C13	−77.8 (2)
C1—C2—C3—C4	0.9 (4)	N3—O3—C13—C12	−101.45 (18)
C2—C3—C4—C5	0.2 (4)	N3—O3—C13—C14	17.9 (2)
C3—C4—C5—C6	−1.1 (4)	C9—C12—C13—O3	−61.8 (2)
C4—C5—C6—C1	1.0 (3)	C9—C12—C13—C14	−175.36 (17)
C4—C5—C6—N2	−177.2 (2)	O3—C13—C14—C15	−17.1 (2)
C2—C1—C6—C5	0.1 (3)	C12—C13—C14—C15	99.0 (2)
N1—C1—C6—C5	−177.46 (19)	O3—N3—C15—C16	−177.74 (17)
C2—C1—C6—N2	178.3 (2)	O3—N3—C15—C14	−1.2 (2)
N1—C1—C6—N2	0.7 (3)	C13—C14—C15—N3	12.0 (2)
C10—N2—C6—C5	−130.1 (2)	C13—C14—C15—C16	−171.60 (18)
C11—N2—C6—C5	41.1 (3)	N3—C15—C16—C21	165.85 (19)
C10—N2—C6—C1	51.7 (3)	C14—C15—C16—C21	−10.3 (3)
C11—N2—C6—C1	−137.1 (2)	N3—C15—C16—C17	−13.0 (3)
C1—N1—C8—O1	−176.2 (2)	C14—C15—C16—C17	170.9 (2)
C7—N1—C8—O1	−4.3 (3)	C21—C16—C17—C18	−1.7 (3)
C1—N1—C8—C9	4.7 (3)	C15—C16—C17—C18	177.11 (19)
C7—N1—C8—C9	176.56 (19)	C16—C17—C18—C19	−0.4 (3)
O1—C8—C9—C12	15.3 (3)	C17—C18—C19—C20	2.0 (3)
N1—C8—C9—C12	−165.63 (18)	C17—C18—C19—Cl1	−177.34 (16)
O1—C8—C9—C10	−107.9 (2)	C18—C19—C20—C21	−1.4 (3)
N1—C8—C9—C10	71.2 (2)	Cl1—C19—C20—C21	177.92 (15)
C6—N2—C10—O2	171.7 (2)	C19—C20—C21—C16	−0.8 (3)
C11—N2—C10—O2	0.3 (3)	C17—C16—C21—C20	2.3 (3)
C6—N2—C10—C9	−10.7 (3)	C15—C16—C21—C20	−176.55 (18)

Experimental details

Crystal data
Chemical formula	C₂₁H₂₀ClN₃O₃
M_r	397.85
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.1821 (1), 9.0741 (1), 13.3792 (2)
α, β, γ (°)	79.748 (1), 80.142 (1), 85.910 (1)
V (Å³)	962.19 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Bruker X8 APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.915, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	19243, 4383, 4056
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.184, 1.03
No. of reflections	4383
No. of parameters	256
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.83, −0.44

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

Acknowledgements

We thank 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 (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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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

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