1,5-Dimethyl-3-propargyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Dardouri, R.; Ouazzani Chahdi, F.; Saffon, N.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536810024219

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1797

doi:10.1107/S1600536810024219

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1,5-Dimethyl-3-propargyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Rachid Dardouri,^a F. Ouazzani Chahdi,^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 21 June 2010; accepted 22 June 2010; online 26 June 2010)

The asymmetric unit of the title compound, C₁₄H₁₄N₂O₂, comprises two independent molecules, which slightly differ in the orientation of the propargyl chain. In both molecules, the diazepine ring adopts a boat conformation with the propargyl-bearing C atom as the prow and the C atoms at the ring junction as the stern. The carbonyl O atom of one independent molecule is hydrogen bonded to the acetylenic H atom of the other independent molecule. In the crystal, symmetry-related molecules are linked together by C—H⋯O hydrogen bonds, forming a ribbon-like structure along the c axis.

Related literature

For a related structure, see: Jabli et al. (2009 ).

Experimental

Crystal data

C₁₄H₁₄N₂O₂
M_r = 242.27
Monoclinic, C c
a = 16.0768 (3) Å
b = 17.1087 (3) Å
c = 8.9530 (2) Å
β = 93.701 (1)°
V = 2457.42 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.40 × 0.30 × 0.05 mm

Data collection

Bruker X8 APEXII area-detector diffractometer
21953 measured reflections
3580 independent reflections
2637 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.105
S = 1.06
3580 reflections
337 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O4	0.93 (3)	2.44 (3)	3.366 (3)	172 (3)
C8—H8⋯O2ⁱ	0.98	2.56	3.536 (3)	175
C19—H19⋯O1ⁱ	0.93	2.49	3.374 (3)	160
Symmetry code: (i) $[x, -y+1, z+{\script{1\over 2}}]$ .

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/S1600536810024219/ci5110sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810024219/ci5110Isup2.hkl

checkCIF report

Comment top

We recently reported the crystal stucture of 1,5-dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione, a compound readily synthesized by reacting the disubstituted 1,5-benzodiazepine-2,4-dione with propargyl bromide (Jabli et al., 2009). The background to the study of such compounds is given in other reports. Replacing the benzyl unit by a methyl unit in the present study gives a compoound having a diazepine ring system (Scheme I, Fig. 1). This ring adopts a boat conformation (with the propargyl-bearing C atom as the prow and the fused-ring C atoms as the stern). There are two independent molecules; the acetylenic H-atom of one molecule forms a hydrogen to the carbonyl O-atom of the other independent molecule.

Related literature top

For a related structure, see: Jabli et al. (2009).

Experimental top

To a solution of potassium t-butoxide (0.42 g, 3.6 mmol) in DMF (15 ml) was added 1,5-dimethyl-1,5-benzodiazepine-2,4-dione (0.50 g, 2.4 mmol) and propargyl bromide (0.26 ml, 2.87 mmol). Stirring was continued for 24 h. The reaction was monitored by thin layer chromatography. On completion of the reaction, the mixture was filtered; crystals were obtained 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. Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of C₁₄H₁₄N₂O₂ at the 50% probability level shown as a hydrogen-bonded dimer; H atoms are drawn as spheres of arbitrary radius. The dashed line denotes a hydrogen bond.

1,5-Dimethyl-3-propargyl-1H-1,5-benzodiazepine- 2,4(3H,5H)-dione top

Crystal data top

C₁₄H₁₄N₂O₂	F(000) = 1024
M_r = 242.27	D_x = 1.310 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 5448 reflections
a = 16.0768 (3) Å	θ = 2.5–29.4°
b = 17.1087 (3) Å	µ = 0.09 mm⁻¹
c = 8.9530 (2) Å	T = 293 K
β = 93.701 (1)°	Plate, colourless
V = 2457.42 (8) Å³	0.40 × 0.30 × 0.05 mm
Z = 8

Data collection top

Bruker X8 APEXII area-detector diffractometer	2637 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.049
Graphite monochromator	θ_max = 30.0°, θ_min = 2.8°
ϕ and ω scans	h = −22→22
21953 measured reflections	k = −24→23
3580 independent reflections	l = −12→12

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0514P)² + 0.5357P] where P = (F_o² + 2F_c²)/3
3580 reflections	(Δ/σ)_max = 0.001
337 parameters	Δρ_max = 0.22 e Å⁻³
4 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₄H₁₄N₂O₂	V = 2457.42 (8) Å³
M_r = 242.27	Z = 8
Monoclinic, Cc	Mo Kα radiation
a = 16.0768 (3) Å	µ = 0.09 mm⁻¹
b = 17.1087 (3) Å	T = 293 K
c = 8.9530 (2) Å	0.40 × 0.30 × 0.05 mm
β = 93.701 (1)°

Data collection top

Bruker X8 APEXII area-detector diffractometer	2637 reflections with I > 2σ(I)
21953 measured reflections	R_int = 0.049
3580 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	4 restraints
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.22 e Å⁻³
3580 reflections	Δρ_min = −0.19 e Å⁻³
337 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.50007 (11)	0.33109 (11)	0.5000 (2)	0.0339 (4)
O2	0.34014 (11)	0.41769 (12)	0.21819 (19)	0.0332 (4)
O3	0.99978 (11)	0.63153 (11)	0.9419 (2)	0.0363 (4)
O4	0.78408 (12)	0.58439 (13)	0.74162 (19)	0.0380 (5)
N1	0.39120 (12)	0.33841 (12)	0.6473 (2)	0.0268 (4)
N2	0.26570 (12)	0.39080 (12)	0.4189 (2)	0.0253 (4)
N3	0.91197 (13)	0.68624 (13)	1.1007 (2)	0.0293 (5)
N4	0.75177 (12)	0.65404 (14)	0.9454 (2)	0.0298 (5)
C1	0.31443 (15)	0.37280 (14)	0.6847 (3)	0.0251 (5)
C2	0.29827 (17)	0.38043 (16)	0.8365 (3)	0.0318 (6)
H2	0.3393	0.3670	0.9099	0.038*
C3	0.22235 (19)	0.40758 (17)	0.8778 (3)	0.0382 (6)
H3	0.2124	0.4121	0.9786	0.046*
C4	0.16095 (18)	0.42805 (17)	0.7692 (3)	0.0384 (6)
H4	0.1091	0.4449	0.7969	0.046*
C5	0.17692 (16)	0.42341 (15)	0.6190 (3)	0.0308 (5)
H5	0.1359	0.4385	0.5467	0.037*
C6	0.25334 (15)	0.39661 (13)	0.5746 (3)	0.0240 (5)
C7	0.33523 (15)	0.41709 (14)	0.3543 (3)	0.0242 (5)
C8	0.40776 (14)	0.44186 (14)	0.4628 (2)	0.0232 (5)
H8	0.3882	0.4782	0.5375	0.028*
C9	0.43852 (14)	0.36629 (14)	0.5383 (3)	0.0250 (5)
C10	0.19504 (16)	0.36807 (17)	0.3156 (3)	0.0329 (6)
H10A	0.2141	0.3334	0.2408	0.049*
H10B	0.1711	0.4139	0.2682	0.049*
H10C	0.1537	0.3421	0.3704	0.049*
C11	0.47672 (15)	0.48013 (16)	0.3774 (3)	0.0295 (5)
H11A	0.4954	0.4434	0.3040	0.035*
H11B	0.4540	0.5255	0.3239	0.035*
C12	0.54896 (16)	0.50462 (16)	0.4769 (3)	0.0324 (5)
C13	0.60798 (19)	0.5229 (2)	0.5539 (4)	0.0446 (7)
H13	0.6549 (15)	0.537 (2)	0.614 (4)	0.062 (11)*
C14	0.42070 (18)	0.26755 (16)	0.7274 (3)	0.0373 (6)
H14A	0.4325	0.2277	0.6563	0.056*
H14B	0.3784	0.2493	0.7898	0.056*
H14C	0.4704	0.2794	0.7884	0.056*
C15	0.83776 (15)	0.68259 (15)	1.1784 (3)	0.0279 (5)
C16	0.84147 (18)	0.69589 (16)	1.3331 (3)	0.0343 (6)
H16	0.8919	0.7095	1.3829	0.041*
C17	0.7709 (2)	0.68902 (17)	1.4124 (3)	0.0404 (7)
H17	0.7745	0.6968	1.5154	0.049*
C18	0.6949 (2)	0.67062 (18)	1.3391 (3)	0.0429 (7)
H18	0.6477	0.6658	1.3932	0.052*
C19	0.68919 (17)	0.65948 (16)	1.1858 (3)	0.0357 (6)
H19	0.6378	0.6481	1.1369	0.043*
C20	0.75997 (16)	0.66527 (14)	1.1039 (3)	0.0278 (5)
C21	0.79742 (15)	0.60039 (16)	0.8740 (3)	0.0281 (5)
C22	0.87014 (15)	0.56424 (15)	0.9697 (3)	0.0274 (5)
H22	0.8497	0.5453	1.0640	0.033*
C23	0.93407 (15)	0.62914 (15)	1.0034 (3)	0.0272 (5)
C24	0.67961 (17)	0.68895 (18)	0.8601 (3)	0.0386 (6)
H24A	0.6957	0.7049	0.7634	0.058*
H24B	0.6605	0.7336	0.9131	0.058*
H24C	0.6356	0.6511	0.8484	0.058*
C25	0.90761 (17)	0.49596 (16)	0.8873 (3)	0.0330 (6)
H25A	0.8631	0.4621	0.8477	0.040*
H25B	0.9365	0.5159	0.8034	0.040*
C26	0.96610 (17)	0.45014 (16)	0.9847 (3)	0.0326 (6)
C27	1.01106 (19)	0.41189 (19)	1.0637 (4)	0.0445 (7)
H27	1.043 (2)	0.3804 (19)	1.130 (4)	0.070 (12)*
C28	0.97458 (18)	0.74656 (18)	1.1443 (4)	0.0426 (7)
H28A	1.0095	0.7556	1.0630	0.064*
H28B	1.0082	0.7291	1.2305	0.064*
H28C	0.9468	0.7942	1.1679	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0256 (9)	0.0397 (10)	0.0365 (11)	0.0051 (8)	0.0020 (7)	−0.0001 (8)
O2	0.0345 (9)	0.0472 (11)	0.0175 (9)	−0.0022 (8)	−0.0014 (7)	0.0014 (8)
O3	0.0284 (10)	0.0455 (11)	0.0350 (11)	−0.0010 (8)	0.0007 (8)	−0.0021 (9)
O4	0.0363 (10)	0.0558 (13)	0.0210 (10)	−0.0022 (9)	−0.0054 (8)	−0.0026 (8)
N1	0.0276 (10)	0.0311 (10)	0.0210 (10)	0.0018 (8)	−0.0029 (8)	0.0052 (9)
N2	0.0234 (10)	0.0323 (11)	0.0197 (10)	−0.0023 (8)	−0.0022 (8)	−0.0003 (8)
N3	0.0267 (10)	0.0350 (12)	0.0254 (11)	−0.0037 (8)	−0.0038 (8)	−0.0050 (9)
N4	0.0256 (10)	0.0398 (12)	0.0233 (11)	−0.0010 (8)	−0.0030 (8)	0.0021 (9)
C1	0.0275 (12)	0.0277 (12)	0.0202 (11)	−0.0040 (9)	0.0019 (9)	0.0009 (10)
C2	0.0372 (13)	0.0376 (14)	0.0204 (12)	−0.0069 (11)	0.0008 (10)	0.0013 (10)
C3	0.0507 (16)	0.0403 (15)	0.0249 (13)	−0.0065 (12)	0.0139 (12)	−0.0015 (12)
C4	0.0376 (15)	0.0383 (15)	0.0411 (16)	−0.0005 (12)	0.0161 (12)	−0.0007 (13)
C5	0.0272 (12)	0.0342 (13)	0.0312 (13)	−0.0017 (10)	0.0034 (10)	0.0002 (11)
C6	0.0256 (11)	0.0261 (11)	0.0202 (11)	−0.0039 (9)	0.0015 (9)	0.0003 (9)
C7	0.0244 (11)	0.0288 (12)	0.0194 (11)	0.0038 (9)	−0.0003 (8)	0.0019 (9)
C8	0.0243 (11)	0.0293 (12)	0.0162 (10)	−0.0010 (9)	0.0022 (8)	−0.0013 (9)
C9	0.0230 (11)	0.0309 (12)	0.0202 (11)	−0.0016 (9)	−0.0056 (9)	−0.0008 (9)
C10	0.0276 (13)	0.0400 (15)	0.0295 (14)	−0.0048 (11)	−0.0102 (10)	−0.0004 (11)
C11	0.0279 (12)	0.0380 (14)	0.0227 (12)	−0.0040 (10)	0.0017 (9)	0.0037 (10)
C12	0.0308 (13)	0.0374 (13)	0.0296 (13)	−0.0036 (11)	0.0060 (11)	0.0054 (11)
C13	0.0379 (15)	0.0542 (19)	0.0412 (17)	−0.0145 (14)	−0.0016 (13)	0.0030 (14)
C14	0.0414 (15)	0.0365 (15)	0.0335 (14)	0.0051 (12)	−0.0019 (11)	0.0121 (12)
C15	0.0316 (13)	0.0288 (13)	0.0231 (12)	0.0016 (10)	−0.0010 (10)	−0.0013 (10)
C16	0.0438 (15)	0.0345 (14)	0.0238 (13)	0.0031 (11)	−0.0047 (11)	−0.0013 (11)
C17	0.0598 (18)	0.0374 (15)	0.0244 (13)	0.0026 (13)	0.0047 (13)	0.0006 (12)
C18	0.0497 (17)	0.0412 (17)	0.0401 (17)	−0.0037 (13)	0.0199 (14)	0.0010 (13)
C19	0.0337 (14)	0.0384 (15)	0.0356 (15)	−0.0055 (11)	0.0056 (12)	−0.0004 (12)
C20	0.0317 (12)	0.0284 (12)	0.0233 (12)	−0.0028 (10)	0.0011 (10)	0.0004 (10)
C21	0.0254 (11)	0.0374 (13)	0.0210 (12)	−0.0078 (10)	−0.0016 (9)	0.0018 (10)
C22	0.0312 (12)	0.0335 (13)	0.0170 (11)	−0.0003 (10)	−0.0016 (9)	0.0007 (10)
C23	0.0250 (11)	0.0353 (13)	0.0202 (12)	0.0019 (9)	−0.0056 (9)	0.0023 (10)
C24	0.0291 (13)	0.0506 (17)	0.0351 (15)	0.0009 (12)	−0.0066 (11)	0.0030 (13)
C25	0.0422 (14)	0.0367 (14)	0.0197 (12)	−0.0012 (11)	−0.0007 (11)	−0.0029 (10)
C26	0.0341 (13)	0.0362 (14)	0.0279 (13)	−0.0034 (11)	0.0051 (10)	−0.0044 (11)
C27	0.0344 (15)	0.0495 (18)	0.0488 (19)	−0.0012 (13)	−0.0036 (13)	0.0078 (14)
C28	0.0351 (14)	0.0497 (17)	0.0423 (17)	−0.0121 (13)	−0.0030 (12)	−0.0113 (14)

Geometric parameters (Å, º) top

O1—C9	1.226 (3)	C11—C12	1.478 (4)
O2—C7	1.226 (3)	C11—H11A	0.97
O3—C23	1.223 (3)	C11—H11B	0.97
O4—C21	1.222 (3)	C12—C13	1.179 (4)
N1—C9	1.361 (3)	C13—H13	0.93 (3)
N1—C1	1.427 (3)	C14—H14A	0.96
N1—C14	1.472 (3)	C14—H14B	0.96
N2—C7	1.367 (3)	C14—H14C	0.96
N2—C6	1.424 (3)	C15—C16	1.401 (3)
N2—C10	1.470 (3)	C15—C20	1.411 (3)
N3—C23	1.371 (3)	C16—C17	1.381 (4)
N3—C15	1.421 (3)	C16—H16	0.93
N3—C28	1.476 (3)	C17—C18	1.385 (4)
N4—C21	1.360 (3)	C17—H17	0.93
N4—C20	1.430 (3)	C18—C19	1.383 (4)
N4—C24	1.473 (3)	C18—H18	0.93
C1—C6	1.406 (3)	C19—C20	1.397 (4)
C1—C2	1.406 (4)	C19—H19	0.93
C2—C3	1.379 (4)	C21—C22	1.535 (3)
C2—H2	0.93	C22—C25	1.526 (4)
C3—C4	1.385 (4)	C22—C23	1.530 (3)
C3—H3	0.93	C22—H22	0.98
C4—C5	1.388 (4)	C24—H24A	0.96
C4—H4	0.93	C24—H24B	0.96
C5—C6	1.393 (4)	C24—H24C	0.96
C5—H5	0.93	C25—C26	1.468 (4)
C7—C8	1.528 (3)	C25—H25A	0.97
C8—C9	1.526 (3)	C25—H25B	0.97
C8—C11	1.534 (3)	C26—C27	1.177 (4)
C8—H8	0.98	C27—H27	0.93 (3)
C10—H10A	0.96	C28—H28A	0.96
C10—H10B	0.96	C28—H28B	0.96
C10—H10C	0.96	C28—H28C	0.96

C9—N1—C1	123.77 (19)	N1—C14—H14A	109.5
C9—N1—C14	117.4 (2)	N1—C14—H14B	109.5
C1—N1—C14	118.8 (2)	H14A—C14—H14B	109.5
C7—N2—C6	124.09 (19)	N1—C14—H14C	109.5
C7—N2—C10	116.2 (2)	H14A—C14—H14C	109.5
C6—N2—C10	118.88 (19)	H14B—C14—H14C	109.5
C23—N3—C15	122.7 (2)	C16—C15—C20	118.8 (2)
C23—N3—C28	117.8 (2)	C16—C15—N3	119.6 (2)
C15—N3—C28	118.7 (2)	C20—C15—N3	121.6 (2)
C21—N4—C20	122.6 (2)	C17—C16—C15	120.7 (2)
C21—N4—C24	117.4 (2)	C17—C16—H16	119.7
C20—N4—C24	118.6 (2)	C15—C16—H16	119.7
C6—C1—C2	119.1 (2)	C16—C17—C18	120.3 (3)
C6—C1—N1	122.0 (2)	C16—C17—H17	119.9
C2—C1—N1	118.8 (2)	C18—C17—H17	119.9
C3—C2—C1	120.8 (2)	C17—C18—C19	120.1 (3)
C3—C2—H2	119.6	C17—C18—H18	120.0
C1—C2—H2	119.6	C19—C18—H18	120.0
C2—C3—C4	120.0 (3)	C18—C19—C20	120.5 (3)
C2—C3—H3	120.0	C18—C19—H19	119.8
C4—C3—H3	120.0	C20—C19—H19	119.8
C3—C4—C5	119.8 (3)	C19—C20—C15	119.6 (2)
C3—C4—H4	120.1	C19—C20—N4	119.1 (2)
C5—C4—H4	120.1	C15—C20—N4	121.3 (2)
C4—C5—C6	121.1 (3)	O4—C21—N4	122.7 (2)
C4—C5—H5	119.4	O4—C21—C22	122.1 (2)
C6—C5—H5	119.4	N4—C21—C22	115.1 (2)
C5—C6—C1	119.0 (2)	C25—C22—C23	111.7 (2)
C5—C6—N2	118.9 (2)	C25—C22—C21	110.40 (19)
C1—C6—N2	122.1 (2)	C23—C22—C21	107.2 (2)
O2—C7—N2	122.0 (2)	C25—C22—H22	109.2
O2—C7—C8	122.3 (2)	C23—C22—H22	109.2
N2—C7—C8	115.7 (2)	C21—C22—H22	109.2
C9—C8—C7	105.00 (19)	O3—C23—N3	121.9 (2)
C9—C8—C11	111.0 (2)	O3—C23—C22	121.6 (2)
C7—C8—C11	110.36 (19)	N3—C23—C22	116.4 (2)
C9—C8—H8	110.1	N4—C24—H24A	109.5
C7—C8—H8	110.1	N4—C24—H24B	109.5
C11—C8—H8	110.1	H24A—C24—H24B	109.5
O1—C9—N1	121.8 (2)	N4—C24—H24C	109.5
O1—C9—C8	122.4 (2)	H24A—C24—H24C	109.5
N1—C9—C8	115.7 (2)	H24B—C24—H24C	109.5
N2—C10—H10A	109.5	C26—C25—C22	112.3 (2)
N2—C10—H10B	109.5	C26—C25—H25A	109.1
H10A—C10—H10B	109.5	C22—C25—H25A	109.1
N2—C10—H10C	109.5	C26—C25—H25B	109.1
H10A—C10—H10C	109.5	C22—C25—H25B	109.1
H10B—C10—H10C	109.5	H25A—C25—H25B	107.9
C12—C11—C8	112.7 (2)	C27—C26—C25	178.0 (3)
C12—C11—H11A	109.1	C26—C27—H27	176 (3)
C8—C11—H11A	109.1	N3—C28—H28A	109.5
C12—C11—H11B	109.1	N3—C28—H28B	109.5
C8—C11—H11B	109.1	H28A—C28—H28B	109.5
H11A—C11—H11B	107.8	N3—C28—H28C	109.5
C13—C12—C11	178.1 (3)	H28A—C28—H28C	109.5
C12—C13—H13	180 (3)	H28B—C28—H28C	109.5

C9—N1—C1—C6	44.7 (3)	C23—N3—C15—C16	131.1 (3)
C14—N1—C1—C6	−133.7 (3)	C28—N3—C15—C16	−38.5 (3)
C9—N1—C1—C2	−137.7 (2)	C23—N3—C15—C20	−48.5 (3)
C14—N1—C1—C2	43.9 (3)	C28—N3—C15—C20	142.0 (3)
C6—C1—C2—C3	2.9 (4)	C20—C15—C16—C17	2.7 (4)
N1—C1—C2—C3	−174.9 (2)	N3—C15—C16—C17	−176.9 (3)
C1—C2—C3—C4	−0.3 (4)	C15—C16—C17—C18	−1.5 (4)
C2—C3—C4—C5	−1.9 (4)	C16—C17—C18—C19	−0.4 (4)
C3—C4—C5—C6	1.6 (4)	C17—C18—C19—C20	1.1 (4)
C4—C5—C6—C1	1.0 (4)	C18—C19—C20—C15	0.0 (4)
C4—C5—C6—N2	178.2 (2)	C18—C19—C20—N4	−179.5 (3)
C2—C1—C6—C5	−3.2 (3)	C16—C15—C20—C19	−1.9 (4)
N1—C1—C6—C5	174.4 (2)	N3—C15—C20—C19	177.7 (2)
C2—C1—C6—N2	179.8 (2)	C16—C15—C20—N4	177.6 (2)
N1—C1—C6—N2	−2.6 (3)	N3—C15—C20—N4	−2.8 (4)
C7—N2—C6—C5	133.8 (2)	C21—N4—C20—C19	−124.8 (3)
C10—N2—C6—C5	−35.1 (3)	C24—N4—C20—C19	41.7 (3)
C7—N2—C6—C1	−49.2 (3)	C21—N4—C20—C15	55.7 (3)
C10—N2—C6—C1	141.9 (2)	C24—N4—C20—C15	−137.8 (2)
C6—N2—C7—O2	−173.0 (2)	C20—N4—C21—O4	171.5 (2)
C10—N2—C7—O2	−3.8 (3)	C24—N4—C21—O4	4.8 (4)
C6—N2—C7—C8	9.9 (3)	C20—N4—C21—C22	−11.6 (3)
C10—N2—C7—C8	179.0 (2)	C24—N4—C21—C22	−178.2 (2)
O2—C7—C8—C9	−109.3 (3)	O4—C21—C22—C25	−12.3 (3)
N2—C7—C8—C9	67.9 (3)	N4—C21—C22—C25	170.7 (2)
O2—C7—C8—C11	10.4 (3)	O4—C21—C22—C23	109.5 (3)
N2—C7—C8—C11	−172.4 (2)	N4—C21—C22—C23	−67.4 (3)
C1—N1—C9—O1	−173.1 (2)	C15—N3—C23—O3	−177.0 (2)
C14—N1—C9—O1	5.3 (3)	C28—N3—C23—O3	−7.4 (4)
C1—N1—C9—C8	4.2 (3)	C15—N3—C23—C22	6.0 (3)
C14—N1—C9—C8	−177.4 (2)	C28—N3—C23—C22	175.6 (2)
C7—C8—C9—O1	100.1 (2)	C25—C22—C23—O3	14.7 (3)
C11—C8—C9—O1	−19.1 (3)	C21—C22—C23—O3	−106.3 (3)
C7—C8—C9—N1	−77.2 (2)	C25—C22—C23—N3	−168.3 (2)
C11—C8—C9—N1	163.55 (19)	C21—C22—C23—N3	70.7 (3)
C9—C8—C11—C12	−63.5 (3)	C23—C22—C25—C26	72.0 (3)
C7—C8—C11—C12	−179.5 (2)	C21—C22—C25—C26	−168.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O4	0.93 (3)	2.44 (3)	3.366 (3)	172 (3)
C8—H8···O2ⁱ	0.98	2.56	3.536 (3)	175
C19—H19···O1ⁱ	0.93	2.49	3.374 (3)	160

Symmetry code: (i) x, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄N₂O₂
M_r	242.27
Crystal system, space group	Monoclinic, Cc
Temperature (K)	293
a, b, c (Å)	16.0768 (3), 17.1087 (3), 8.9530 (2)
β (°)	93.701 (1)
V (Å³)	2457.42 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.30 × 0.05

Data collection
Diffractometer	Bruker X8 APEXII area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	21953, 3580, 2637
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.105, 1.06
No. of reflections	3580
No. of parameters	337
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.19

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), 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
C13—H13···O4	0.93 (3)	2.44 (3)	3.366 (3)	172 (3)
C8—H8···O2ⁱ	0.98	2.56	3.536 (3)	175
C19—H19···O1ⁱ	0.93	2.49	3.374 (3)	160

Symmetry code: (i) x, −y+1, z+1/2.

Acknowledgements

The authors 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
Jabli, H., Ouazzani Chahdi, F., Garrigues, B., Essassi, E. M. & Ng, S. W. (2009). Acta Cryst. E65, o3149. Web of Science CSD CrossRef IUCr Journals 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. Submitted. Google Scholar