1,5-Dibenzyl-3-propargyl-1,5-benzo­diazepine-2,4-dione

Jabli, H.; Ouazzani Chahdi, F.; Garrigues, B.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536809048508

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3149

doi:10.1107/S1600536809048508

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1,5-Dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione

Hind Jabli,^a F. Ouazzani Chahdi,^a Bernard Garrigues,^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, ^bLaboratoire de Hétérochimie Fondamentale et Appliquée, Université Paul Sabatier, Toulouse, France, ^cLaboratoire de Chimie Organique Hétérocyclique, Pôle de compétences Pharmacochimie, Université Mohammed V-Agdal, B.P. 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 12 November 2009; accepted 15 November 2009; online 21 November 2009)

The title compound, C₂₆H₂₂N₂O₂, features a benzene ring fused with a seven-membered diazepine ring; the latter ring adopts a boat conformation (with the propargylallyl-bearing C atom as the prow and the fused-ring C atoms as the stern). The phenyl ring of one of the two benzyl substituents is disordered over two positions in a 0.812 (11):0.188 (11) ratio.

Related literature

For the crystal structure of the parent compound, benzodiazepin-2,4-dione, see: Négrier et al. (2006 ).

Experimental

Crystal data

C₂₆H₂₂N₂O₂
M_r = 394.46
Monoclinic, P 2₁ /c
a = 8.8663 (2) Å
b = 18.6771 (4) Å
c = 12.4665 (3) Å
β = 91.154 (1)°
V = 2063.99 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 193 K
0.70 × 0.50 × 0.30 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: none
29296 measured reflections
4750 independent reflections
3931 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.112
S = 1.02
4750 reflections
278 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.27 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048508/sj2679sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048508/sj2679Isup2.hkl

checkCIF report

Related literature top

For the crystal structure of the parent compound, benzodiazepin-2,4-dione, see: Négrier et al. (2006).

Experimental top

To a solution of the potassium t-butoxide (0.24 g, 2.13 mmol) in THF (15 ml) was added 1,5-dibenzyl-1,5-benzodiazepine-2,4-dione (0.50 g, 1.40 mmol) and propargyl bromide (0.20 ml, 1.88 mmol). Stirring was continued for 24 h. The reaction was monitored by thin layer chromatography. The mixture was filtered and the solution evaporated to give colorless crystals.

A somewhat large crystal was used in the diffraction measurements.

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, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₆H₂₂N₂O₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in one of the phenyl rings is not shown.

1,5-Dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione top

Crystal data top

C₂₆H₂₂N₂O₂	F(000) = 832
M_r = 394.46	D_x = 1.269 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9973 reflections
a = 8.8663 (2) Å	θ = 2.5–32.9°
b = 18.6771 (4) Å	µ = 0.08 mm⁻¹
c = 12.4665 (3) Å	T = 193 K
β = 91.154 (1)°	Irregular block, colorless
V = 2063.99 (8) Å³	0.70 × 0.50 × 0.30 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	3931 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 27.5°, θ_min = 2.0°
ϕ and ω scans	h = −11→11
29296 measured reflections	k = −24→18
4750 independent reflections	l = −16→15

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0579P)² + 0.5557P] where P = (F_o² + 2F_c²)/3
4750 reflections	(Δ/σ)_max = 0.001
278 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₆H₂₂N₂O₂	V = 2063.99 (8) Å³
M_r = 394.46	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.8663 (2) Å	µ = 0.08 mm⁻¹
b = 18.6771 (4) Å	T = 193 K
c = 12.4665 (3) Å	0.70 × 0.50 × 0.30 mm
β = 91.154 (1)°

Data collection top

Bruker APEXII diffractometer	3931 reflections with I > 2σ(I)
29296 measured reflections	R_int = 0.027
4750 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.112	H-atom parameters constrained
S = 1.02	Δρ_max = 0.26 e Å⁻³
4750 reflections	Δρ_min = −0.27 e Å⁻³
278 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.17022 (9)	0.29934 (4)	0.63891 (7)	0.0310 (2)
O2	−0.09780 (10)	0.44893 (5)	0.68067 (8)	0.0408 (2)
N1	0.34007 (10)	0.38740 (5)	0.67524 (7)	0.0250 (2)
N2	0.12855 (11)	0.50134 (5)	0.71936 (7)	0.0264 (2)
C1	0.20965 (12)	0.36186 (6)	0.62971 (8)	0.0238 (2)
C2	0.03474 (13)	0.45816 (6)	0.66023 (9)	0.0268 (2)
C3	0.11097 (12)	0.41712 (6)	0.57026 (8)	0.0238 (2)
H3	0.1753	0.4501	0.5277	0.029*
C4	−0.00697 (13)	0.38106 (6)	0.49721 (9)	0.0285 (2)
H4A	−0.0646	0.3461	0.5398	0.034*
H4B	−0.0787	0.4178	0.4701	0.034*
C5	0.05908 (14)	0.34408 (7)	0.40583 (10)	0.0334 (3)
C6	0.11070 (17)	0.31415 (8)	0.33138 (12)	0.0461 (3)
H6	0.1521	0.2901	0.2716	0.055*
C7	0.38435 (13)	0.46069 (6)	0.67074 (8)	0.0249 (2)
C8	0.28132 (13)	0.51554 (6)	0.69185 (8)	0.0255 (2)
C9	0.33036 (15)	0.58677 (7)	0.68953 (10)	0.0332 (3)
H9	0.2605	0.6244	0.7011	0.040*
C10	0.47975 (16)	0.60272 (7)	0.67056 (10)	0.0384 (3)
H10	0.5122	0.6512	0.6700	0.046*
C11	0.58233 (15)	0.54818 (7)	0.65236 (10)	0.0369 (3)
H11	0.6853	0.5593	0.6410	0.044*
C12	0.53473 (14)	0.47752 (7)	0.65072 (9)	0.0314 (3)
H12	0.6046	0.4404	0.6359	0.038*
C13	0.43658 (14)	0.33760 (7)	0.73776 (10)	0.0320 (3)
H13A	0.4796	0.3649	0.7991	0.038*	0.188 (11)
H13B	0.3695	0.3008	0.7681	0.038*	0.188 (11)
H13C	0.3715	0.3028	0.7748	0.038*	0.812 (11)
H13D	0.4930	0.3650	0.7934	0.038*	0.812 (11)
C14'	0.5525 (9)	0.3026 (8)	0.6915 (10)	0.0290 (5)	0.188 (11)
C15'	0.6972 (11)	0.3031 (7)	0.7365 (9)	0.0426 (6)	0.188 (11)
H15'	0.7173	0.3290	0.8008	0.051*	0.188 (11)
C16'	0.8126 (8)	0.2659 (7)	0.6873 (11)	0.0480 (10)	0.188 (11)
H16'	0.9115	0.2663	0.7180	0.058*	0.188 (11)
C17'	0.7832 (12)	0.2281 (6)	0.5931 (12)	0.0511 (8)	0.188 (11)
H17'	0.8621	0.2026	0.5595	0.061*	0.188 (11)
C18'	0.6385 (14)	0.2275 (8)	0.5482 (12)	0.0728 (9)	0.188 (11)
H18'	0.6184	0.2017	0.4838	0.087*	0.188 (11)
C19'	0.5231 (10)	0.2648 (9)	0.5974 (11)	0.0567 (7)	0.188 (11)
H19'	0.4242	0.2644	0.5667	0.068*	0.188 (11)
C14	0.5505 (2)	0.29604 (17)	0.6685 (3)	0.0290 (5)	0.812 (11)
C15	0.6962 (2)	0.28451 (19)	0.7075 (3)	0.0426 (6)	0.812 (11)
H15	0.7261	0.3039	0.7751	0.051*	0.812 (11)
C16	0.7990 (2)	0.2450 (2)	0.6492 (4)	0.0480 (10)	0.812 (11)
H16	0.8979	0.2373	0.6775	0.058*	0.812 (11)
C17	0.7587 (3)	0.21739 (14)	0.5519 (4)	0.0511 (8)	0.812 (11)
H17	0.8288	0.1903	0.5121	0.061*	0.812 (11)
C18	0.6154 (3)	0.22919 (19)	0.5119 (4)	0.0728 (9)	0.812 (11)
H18	0.5870	0.2105	0.4436	0.087*	0.812 (11)
C19	0.5119 (3)	0.2679 (2)	0.5699 (3)	0.0567 (7)	0.812 (11)
H19	0.4131	0.2752	0.5412	0.068*	0.812 (11)
C20	0.07850 (14)	0.52656 (7)	0.82584 (9)	0.0313 (3)
H20A	−0.0327	0.5235	0.8295	0.038*
H20B	0.1083	0.5772	0.8365	0.038*
C21	0.15023 (14)	0.48060 (7)	0.91273 (9)	0.0305 (3)
C22	0.11027 (17)	0.40885 (7)	0.92212 (10)	0.0396 (3)
H22	0.0354	0.3893	0.8751	0.047*
C23	0.17857 (19)	0.36561 (8)	0.99950 (12)	0.0482 (4)
H23	0.1511	0.3166	1.0048	0.058*
C24	0.28666 (18)	0.39393 (9)	1.06888 (11)	0.0505 (4)
H24	0.3327	0.3645	1.1224	0.061*
C25	0.32761 (19)	0.46476 (10)	1.06047 (12)	0.0522 (4)
H25	0.4021	0.4841	1.1080	0.063*
C26	0.25989 (16)	0.50798 (8)	0.98237 (11)	0.0415 (3)
H26	0.2890	0.5568	0.9767	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0302 (4)	0.0243 (4)	0.0384 (4)	−0.0013 (3)	−0.0020 (3)	0.0049 (3)
O2	0.0226 (4)	0.0483 (6)	0.0516 (6)	0.0013 (4)	0.0039 (4)	−0.0121 (4)
N1	0.0235 (5)	0.0243 (5)	0.0272 (4)	0.0033 (4)	−0.0028 (4)	0.0014 (3)
N2	0.0249 (5)	0.0275 (5)	0.0269 (5)	0.0028 (4)	0.0014 (4)	−0.0024 (4)
C1	0.0232 (5)	0.0249 (5)	0.0233 (5)	0.0015 (4)	0.0013 (4)	0.0008 (4)
C2	0.0236 (6)	0.0262 (5)	0.0306 (5)	0.0040 (4)	−0.0011 (4)	0.0010 (4)
C3	0.0239 (5)	0.0228 (5)	0.0246 (5)	0.0006 (4)	−0.0020 (4)	0.0015 (4)
C4	0.0272 (6)	0.0279 (6)	0.0302 (5)	−0.0007 (4)	−0.0063 (4)	0.0013 (4)
C5	0.0338 (6)	0.0305 (6)	0.0355 (6)	−0.0041 (5)	−0.0096 (5)	−0.0020 (5)
C6	0.0457 (8)	0.0493 (8)	0.0430 (7)	−0.0003 (7)	−0.0068 (6)	−0.0156 (6)
C7	0.0257 (5)	0.0264 (5)	0.0225 (5)	−0.0006 (4)	−0.0021 (4)	−0.0012 (4)
C8	0.0251 (6)	0.0279 (5)	0.0234 (5)	−0.0006 (4)	−0.0018 (4)	−0.0010 (4)
C9	0.0369 (7)	0.0268 (6)	0.0358 (6)	0.0002 (5)	−0.0030 (5)	−0.0029 (5)
C10	0.0424 (7)	0.0309 (6)	0.0417 (7)	−0.0111 (5)	−0.0010 (6)	−0.0012 (5)
C11	0.0301 (6)	0.0435 (7)	0.0371 (6)	−0.0114 (5)	0.0023 (5)	−0.0031 (5)
C12	0.0260 (6)	0.0363 (6)	0.0318 (6)	−0.0005 (5)	0.0013 (4)	−0.0035 (5)
C13	0.0311 (6)	0.0324 (6)	0.0322 (6)	0.0037 (5)	−0.0096 (5)	0.0045 (5)
C14'	0.0251 (6)	0.0232 (8)	0.0384 (13)	0.0018 (5)	−0.0039 (7)	0.0042 (8)
C15'	0.0285 (7)	0.0577 (15)	0.0414 (14)	0.0039 (9)	−0.0049 (8)	0.0094 (11)
C16'	0.0246 (8)	0.0538 (16)	0.066 (2)	0.0098 (9)	0.0024 (10)	0.0223 (16)
C17'	0.0350 (11)	0.0326 (9)	0.086 (2)	0.0053 (8)	0.0170 (12)	−0.0031 (11)
C18'	0.0433 (12)	0.0895 (15)	0.086 (2)	0.0116 (11)	−0.0022 (13)	−0.0534 (17)
C19'	0.0300 (8)	0.0751 (12)	0.0647 (18)	0.0138 (8)	−0.0097 (9)	−0.0338 (14)
C14	0.0251 (6)	0.0232 (8)	0.0384 (13)	0.0018 (5)	−0.0039 (7)	0.0042 (8)
C15	0.0285 (7)	0.0577 (15)	0.0414 (14)	0.0039 (9)	−0.0049 (8)	0.0094 (11)
C16	0.0246 (8)	0.0538 (16)	0.066 (2)	0.0098 (9)	0.0024 (10)	0.0223 (16)
C17	0.0350 (11)	0.0326 (9)	0.086 (2)	0.0053 (8)	0.0170 (12)	−0.0031 (11)
C18	0.0433 (12)	0.0895 (15)	0.086 (2)	0.0116 (11)	−0.0022 (13)	−0.0534 (17)
C19	0.0300 (8)	0.0751 (12)	0.0647 (18)	0.0138 (8)	−0.0097 (9)	−0.0338 (14)
C20	0.0313 (6)	0.0314 (6)	0.0313 (6)	0.0061 (5)	0.0046 (5)	−0.0057 (5)
C21	0.0294 (6)	0.0350 (6)	0.0273 (5)	0.0027 (5)	0.0070 (4)	−0.0035 (4)
C22	0.0442 (8)	0.0391 (7)	0.0355 (6)	−0.0043 (6)	0.0008 (5)	−0.0016 (5)
C23	0.0620 (10)	0.0395 (7)	0.0433 (7)	0.0013 (7)	0.0074 (7)	0.0067 (6)
C24	0.0524 (9)	0.0622 (10)	0.0369 (7)	0.0101 (8)	0.0009 (6)	0.0118 (7)
C25	0.0473 (9)	0.0694 (10)	0.0394 (7)	−0.0062 (8)	−0.0092 (6)	0.0018 (7)
C26	0.0430 (8)	0.0436 (7)	0.0378 (7)	−0.0062 (6)	−0.0010 (6)	−0.0024 (6)

Geometric parameters (Å, º) top

O1—C1	1.2248 (13)	C15'—C16'	1.3900
O2—C2	1.2197 (15)	C15'—H15'	0.9500
N1—C1	1.3640 (14)	C16'—C17'	1.3900
N1—C7	1.4254 (14)	C16'—H16'	0.9500
N1—C13	1.4758 (14)	C17'—C18'	1.3900
N2—C2	1.3641 (15)	C17'—H17'	0.9500
N2—C8	1.4288 (15)	C18'—C19'	1.3900
N2—C20	1.4847 (14)	C18'—H18'	0.9500
C1—C3	1.5342 (14)	C19'—H19'	0.9500
C2—C3	1.5274 (15)	C14—C19	1.373 (2)
C3—C4	1.5291 (15)	C14—C15	1.388 (2)
C3—H3	1.0000	C15—C16	1.389 (3)
C4—C5	1.4645 (18)	C15—H15	0.9500
C4—H4A	0.9900	C16—C17	1.359 (3)
C4—H4B	0.9900	C16—H16	0.9500
C5—C6	1.1833 (19)	C17—C18	1.373 (3)
C6—H6	0.9500	C17—H17	0.9500
C7—C12	1.3972 (17)	C18—C19	1.384 (3)
C7—C8	1.4010 (16)	C18—H18	0.9500
C8—C9	1.4001 (17)	C19—H19	0.9500
C9—C10	1.3826 (19)	C20—C21	1.5122 (17)
C9—H9	0.9500	C20—H20A	0.9900
C10—C11	1.387 (2)	C20—H20B	0.9900
C10—H10	0.9500	C21—C26	1.3880 (18)
C11—C12	1.3856 (18)	C21—C22	1.3918 (18)
C11—H11	0.9500	C22—C23	1.388 (2)
C12—H12	0.9500	C22—H22	0.9500
C13—C14'	1.356 (8)	C23—C24	1.383 (2)
C13—C14	1.550 (3)	C23—H23	0.9500
C13—H13A	0.9900	C24—C25	1.376 (2)
C13—H13B	0.9900	C24—H24	0.9500
C13—H13C	0.9900	C25—C26	1.392 (2)
C13—H13D	0.9900	C25—H25	0.9500
C14'—C15'	1.3900	C26—H26	0.9500
C14'—C19'	1.3900

C1—N1—C7	123.46 (9)	C13—C14'—C15'	121.8 (7)
C1—N1—C13	118.49 (9)	C13—C14'—C19'	118.2 (7)
C7—N1—C13	117.96 (9)	C15'—C14'—C19'	120.0
C2—N2—C8	123.41 (9)	C14'—C15'—C16'	120.0
C2—N2—C20	118.73 (10)	C14'—C15'—H15'	120.0
C8—N2—C20	117.23 (9)	C16'—C15'—H15'	120.0
O1—C1—N1	122.39 (10)	C15'—C16'—C17'	120.0
O1—C1—C3	121.70 (10)	C15'—C16'—H16'	120.0
N1—C1—C3	115.86 (9)	C17'—C16'—H16'	120.0
O2—C2—N2	123.38 (11)	C18'—C17'—C16'	120.0
O2—C2—C3	121.66 (10)	C18'—C17'—H17'	120.0
N2—C2—C3	114.81 (10)	C16'—C17'—H17'	120.0
C2—C3—C4	110.55 (9)	C19'—C18'—C17'	120.0
C2—C3—C1	103.86 (8)	C19'—C18'—H18'	120.0
C4—C3—C1	111.59 (9)	C17'—C18'—H18'	120.0
C2—C3—H3	110.2	C18'—C19'—C14'	120.0
C4—C3—H3	110.2	C18'—C19'—H19'	120.0
C1—C3—H3	110.2	C14'—C19'—H19'	120.0
C5—C4—C3	113.06 (10)	C19—C14—C15	117.86 (16)
C5—C4—H4A	109.0	C19—C14—C13	122.45 (17)
C3—C4—H4A	109.0	C15—C14—C13	119.66 (16)
C5—C4—H4B	109.0	C14—C15—C16	120.98 (18)
C3—C4—H4B	109.0	C14—C15—H15	119.5
H4A—C4—H4B	107.8	C16—C15—H15	119.5
C6—C5—C4	179.17 (14)	C17—C16—C15	120.36 (17)
C5—C6—H6	180.0	C17—C16—H16	119.8
C12—C7—C8	119.81 (10)	C15—C16—H16	119.8
C12—C7—N1	119.19 (10)	C16—C17—C18	119.18 (18)
C8—C7—N1	120.91 (10)	C16—C17—H17	120.4
C9—C8—C7	119.14 (11)	C18—C17—H17	120.4
C9—C8—N2	118.53 (10)	C17—C18—C19	120.8 (2)
C7—C8—N2	122.29 (10)	C17—C18—H18	119.6
C10—C9—C8	120.48 (12)	C19—C18—H18	119.6
C10—C9—H9	119.8	C14—C19—C18	120.79 (18)
C8—C9—H9	119.8	C14—C19—H19	119.6
C9—C10—C11	120.21 (12)	C18—C19—H19	119.6
C9—C10—H10	119.9	N2—C20—C21	109.35 (9)
C11—C10—H10	119.9	N2—C20—H20A	109.8
C12—C11—C10	120.08 (12)	C21—C20—H20A	109.8
C12—C11—H11	120.0	N2—C20—H20B	109.8
C10—C11—H11	120.0	C21—C20—H20B	109.8
C11—C12—C7	120.21 (12)	H20A—C20—H20B	108.3
C11—C12—H12	119.9	C26—C21—C22	118.58 (12)
C7—C12—H12	119.9	C26—C21—C20	121.21 (12)
C14'—C13—N1	121.1 (6)	C22—C21—C20	120.18 (11)
N1—C13—C14	113.51 (14)	C23—C22—C21	120.70 (13)
C14'—C13—H13A	107.1	C23—C22—H22	119.7
N1—C13—H13A	107.1	C21—C22—H22	119.7
C14—C13—H13A	116.3	C24—C23—C22	119.96 (14)
C14'—C13—H13B	107.1	C24—C23—H23	120.0
N1—C13—H13B	107.1	C22—C23—H23	120.0
C14—C13—H13B	105.6	C25—C24—C23	120.03 (14)
H13A—C13—H13B	106.8	C25—C24—H24	120.0
C14'—C13—H13C	109.6	C23—C24—H24	120.0
N1—C13—H13C	108.9	C24—C25—C26	120.00 (14)
C14—C13—H13C	108.9	C24—C25—H25	120.0
H13A—C13—H13C	101.4	C26—C25—H25	120.0
N1—C13—H13D	108.9	C21—C26—C25	120.73 (14)
C14—C13—H13D	108.9	C21—C26—H26	119.6
H13C—C13—H13D	107.7	C25—C26—H26	119.6

C7—N1—C1—O1	−176.41 (10)	C1—N1—C13—C14	87.11 (17)
C13—N1—C1—O1	−0.01 (16)	C7—N1—C13—C14	−96.30 (16)
C7—N1—C1—C3	0.87 (15)	N1—C13—C14'—C15'	128.9 (7)
C13—N1—C1—C3	177.26 (9)	C14—C13—C14'—C15'	169 (5)
C8—N2—C2—O2	−176.15 (11)	N1—C13—C14'—C19'	−51.8 (9)
C20—N2—C2—O2	13.17 (17)	C14—C13—C14'—C19'	−11 (4)
C8—N2—C2—C3	8.29 (15)	C13—C14'—C15'—C16'	179.3 (12)
C20—N2—C2—C3	−162.38 (9)	C19'—C14'—C15'—C16'	0.0
O2—C2—C3—C4	14.32 (15)	C14'—C15'—C16'—C17'	0.0
N2—C2—C3—C4	−170.04 (9)	C15'—C16'—C17'—C18'	0.0
O2—C2—C3—C1	−105.49 (12)	C16'—C17'—C18'—C19'	0.0
N2—C2—C3—C1	70.14 (11)	C17'—C18'—C19'—C14'	0.0
O1—C1—C3—C2	100.64 (12)	C13—C14'—C19'—C18'	−179.3 (12)
N1—C1—C3—C2	−76.66 (11)	C15'—C14'—C19'—C18'	0.0
O1—C1—C3—C4	−18.46 (15)	C14'—C13—C14—C19	175 (5)
N1—C1—C3—C4	164.24 (9)	N1—C13—C14—C19	−41.8 (3)
C2—C3—C4—C5	176.83 (9)	C14'—C13—C14—C15	−3 (4)
C1—C3—C4—C5	−68.12 (12)	N1—C13—C14—C15	140.1 (2)
C1—N1—C7—C12	−137.80 (11)	C19—C14—C15—C16	−0.8 (3)
C13—N1—C7—C12	45.79 (14)	C13—C14—C15—C16	177.4 (2)
C1—N1—C7—C8	45.72 (15)	C14—C15—C16—C17	0.6 (3)
C13—N1—C7—C8	−130.69 (11)	C15—C16—C17—C18	0.2 (3)
C12—C7—C8—C9	1.77 (16)	C16—C17—C18—C19	−0.8 (4)
N1—C7—C8—C9	178.23 (10)	C15—C14—C19—C18	0.2 (3)
C12—C7—C8—N2	−176.05 (10)	C13—C14—C19—C18	−177.9 (3)
N1—C7—C8—N2	0.41 (15)	C17—C18—C19—C14	0.6 (4)
C2—N2—C8—C9	130.25 (12)	C2—N2—C20—C21	99.41 (12)
C20—N2—C8—C9	−58.95 (14)	C8—N2—C20—C21	−71.84 (13)
C2—N2—C8—C7	−51.91 (15)	N2—C20—C21—C26	110.77 (13)
C20—N2—C8—C7	118.89 (11)	N2—C20—C21—C22	−67.23 (15)
C7—C8—C9—C10	−2.35 (17)	C26—C21—C22—C23	0.0 (2)
N2—C8—C9—C10	175.55 (11)	C20—C21—C22—C23	178.08 (12)
C8—C9—C10—C11	0.75 (19)	C21—C22—C23—C24	0.6 (2)
C9—C10—C11—C12	1.46 (19)	C22—C23—C24—C25	−0.7 (2)
C10—C11—C12—C7	−2.03 (19)	C23—C24—C25—C26	0.2 (2)
C8—C7—C12—C11	0.40 (17)	C22—C21—C26—C25	−0.5 (2)
N1—C7—C12—C11	−176.12 (10)	C20—C21—C26—C25	−178.52 (13)
C1—N1—C13—C14'	93.9 (7)	C24—C25—C26—C21	0.4 (2)
C7—N1—C13—C14'	−89.5 (7)

Experimental details

Crystal data
Chemical formula	C₂₆H₂₂N₂O₂
M_r	394.46
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	8.8663 (2), 18.6771 (4), 12.4665 (3)
β (°)	91.154 (1)
V (Å³)	2063.99 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.70 × 0.50 × 0.30

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	29296, 4750, 3931
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.112, 1.02
No. of reflections	4750
No. of parameters	278
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.27

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

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 (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Négrier, Ph., Mondieig, D., Léger, J. M., Benali, B., Lazar, Z., Boucetta, A., Elassyry, A., Lakhrissi, B., Jermoumi, C. & Massoui, M. (2006). Anal. Sci. X-ray Struct. Anal. Online, 22, 175. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar