1,3-Dimethyl-3-tetra­decyl-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/S1600536811005782

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o674

doi:10.1107/S1600536811005782

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

Rachid Dardouri,^a Fouad Ouazzani Chahdi,^a Natalie Saffon,^b El Mokhtar Essassi ^a and Seik Weng Ng ^c ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, B.P. 1014 Avenue Ibn Batout, Rabat, Morocco, ^bService Commun Rayons-X FR2599, Université Paul Sabatier, Bâtiment 2R1, 118 route de Narbonne, Toulouse, France, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 13 February 2011; accepted 16 February 2011; online 19 February 2011)

The seven-membered ring of the title compound, C₂₅H₄₀N₂O₂, 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 tetradecyl substituent occupies an equatorial position, with the tetradodecyl chain exhibibiting an an all-trans conformation.

Related literature

For the crystal structure of the 12-bromododecyl-substituted analog, see: Dardouri et al. (2010 ).

Experimental

Crystal data

C₂₅H₄₀N₂O₂
M_r = 400.59
Monoclinic, P 2₁ /c
a = 8.1286 (1) Å
b = 33.5899 (5) Å
c = 9.4095 (2) Å
β = 114.640 (1)°
V = 2335.22 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 295 K
0.20 × 0.02 × 0.02 mm

Data collection

Bruker X8 APEXII diffractometer
29471 measured reflections
5359 independent reflections
3671 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.139
S = 1.03
5359 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.19 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/S1600536811005782/bt5477sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811005782/bt5477Isup2.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 1,12-dibromododecane to give the 12-bromododecyl substitued derivative (Dardouri et al., 2010). The corresponding tetradecyl title compound (Scheme I, Fig. 1) was obtained by using 1-bromotetradecane.

Related literature top

For the crystal structure of the 12-bromododecyl-substituted analog, see: Dardouri et al. (2010).

Experimental top

To a solution of the 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 1-bromotetradecane (0.78 ml, 2.88 mmol). Stirring was continued for 24 h. The reaction was monitored by thin layer ch romatography. The mixture was filtered and the solution evaporated to give colorless crystals.

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 C₂₅H₄₀N₂O₂ at the 50% probability level; hydrogen atoms are drawn as arbitrary radius.

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

Crystal data top

C₂₅H₄₀N₂O₂	F(000) = 880
M_r = 400.59	D_x = 1.139 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5173 reflections
a = 8.1286 (1) Å	θ = 2.5–26.9°
b = 33.5899 (5) Å	µ = 0.07 mm⁻¹
c = 9.4095 (2) Å	T = 295 K
β = 114.640 (1)°	Plate, colorless
V = 2335.22 (7) Å³	0.20 × 0.02 × 0.02 mm
Z = 4

Data collection top

Bruker X8 APEXII diffractometer	3671 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.044
Graphite monochromator	θ_max = 27.5°, θ_min = 2.5°
ϕ and ω scans	h = −10→10
29471 measured reflections	k = −43→43
5359 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0639P)² + 0.5157P] where P = (F_o² + 2F_c²)/3
5359 reflections	(Δ/σ)_max = 0.001
264 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₅H₄₀N₂O₂	V = 2335.22 (7) Å³
M_r = 400.59	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1286 (1) Å	µ = 0.07 mm⁻¹
b = 33.5899 (5) Å	T = 295 K
c = 9.4095 (2) Å	0.20 × 0.02 × 0.02 mm
β = 114.640 (1)°

Data collection top

Bruker X8 APEXII diffractometer	3671 reflections with I > 2σ(I)
29471 measured reflections	R_int = 0.044
5359 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.03	Δρ_max = 0.23 e Å⁻³
5359 reflections	Δρ_min = −0.19 e Å⁻³
264 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.17583 (14)	0.70600 (3)	0.42788 (12)	0.0335 (3)
O2	−0.24455 (15)	0.66528 (3)	0.46476 (13)	0.0383 (3)
N1	−0.04415 (16)	0.72024 (4)	0.19047 (14)	0.0286 (3)
N2	−0.36308 (16)	0.69006 (4)	0.21941 (14)	0.0280 (3)
C1	−0.2029 (2)	0.70901 (4)	0.05774 (17)	0.0288 (3)
C2	−0.2041 (3)	0.71320 (5)	−0.09017 (19)	0.0405 (4)
H2	−0.1015	0.7227	−0.0994	0.049*
C3	−0.3559 (3)	0.70346 (6)	−0.2228 (2)	0.0492 (5)
H3	−0.3547	0.7059	−0.3208	0.059*
C4	−0.5087 (3)	0.69014 (5)	−0.2098 (2)	0.0485 (5)
H4	−0.6116	0.6839	−0.2992	0.058*
C5	−0.5099 (2)	0.68592 (5)	−0.06424 (19)	0.0393 (4)
H5	−0.6144	0.6770	−0.0567	0.047*
C6	−0.3568 (2)	0.69484 (4)	0.07174 (17)	0.0281 (3)
C7	−0.2317 (2)	0.67078 (4)	0.34230 (17)	0.0261 (3)
C8	−0.06497 (19)	0.65811 (4)	0.31754 (16)	0.0240 (3)
H8	−0.1044	0.6453	0.2150	0.029*
C9	0.03579 (19)	0.69634 (4)	0.31786 (16)	0.0253 (3)
C10	−0.5273 (2)	0.70170 (5)	0.2374 (2)	0.0408 (4)
H10A	−0.4948	0.7121	0.3407	0.061*
H10B	−0.6041	0.6789	0.2217	0.061*
H10C	−0.5907	0.7218	0.1616	0.061*
C11	0.0474 (2)	0.75737 (5)	0.1834 (2)	0.0390 (4)
H11A	0.1248	0.7658	0.2875	0.059*
H11B	−0.0413	0.7776	0.1330	0.059*
H11C	0.1185	0.7530	0.1251	0.059*
C12	0.0535 (2)	0.62912 (5)	0.44311 (17)	0.0282 (3)
H12A	0.1026	0.6426	0.5433	0.034*
H12B	−0.0207	0.6072	0.4499	0.034*
C13	0.2087 (2)	0.61250 (5)	0.41109 (17)	0.0320 (4)
H13A	0.2758	0.6345	0.3939	0.038*
H13B	0.1594	0.5968	0.3160	0.038*
C14	0.3380 (2)	0.58674 (5)	0.54351 (17)	0.0303 (3)
H14A	0.3848	0.6023	0.6390	0.036*
H14B	0.2711	0.5645	0.5590	0.036*
C15	0.4961 (2)	0.57070 (5)	0.51467 (18)	0.0314 (4)
H15A	0.5619	0.5929	0.4974	0.038*
H15B	0.4496	0.5547	0.4203	0.038*
C16	0.6259 (2)	0.54562 (5)	0.64913 (17)	0.0304 (3)
H16A	0.5594	0.5237	0.6672	0.037*
H16B	0.6732	0.5618	0.7431	0.037*
C17	0.7836 (2)	0.52895 (5)	0.62100 (17)	0.0302 (3)
H17A	0.8486	0.5508	0.6007	0.036*
H17B	0.7365	0.5123	0.5285	0.036*
C18	0.9155 (2)	0.50462 (5)	0.75784 (17)	0.0307 (3)
H18A	0.9618	0.5213	0.8505	0.037*
H18B	0.8505	0.4827	0.7777	0.037*
C19	1.0743 (2)	0.48805 (5)	0.73090 (17)	0.0309 (3)
H19A	1.1351	0.5098	0.7048	0.037*
H19B	1.0286	0.4701	0.6422	0.037*
C20	1.2114 (2)	0.46592 (5)	0.87169 (18)	0.0331 (4)
H20A	1.2563	0.4839	0.9604	0.040*
H20B	1.1503	0.4441	0.8975	0.040*
C21	1.3712 (2)	0.44929 (5)	0.84705 (18)	0.0333 (4)
H21A	1.4266	0.4706	0.8128	0.040*
H21B	1.3276	0.4296	0.7643	0.040*
C22	1.5143 (2)	0.43030 (5)	0.99273 (18)	0.0323 (4)
H22A	1.4584	0.4092	1.0276	0.039*
H22B	1.5587	0.4501	1.0750	0.039*
C23	1.6742 (2)	0.41310 (5)	0.96896 (18)	0.0332 (4)
H23A	1.6318	0.3914	0.8942	0.040*
H23B	1.7234	0.4335	0.9248	0.040*
C24	1.8235 (2)	0.39779 (5)	1.11869 (19)	0.0349 (4)
H24A	1.7718	0.3792	1.1678	0.042*
H24B	1.8733	0.4200	1.1898	0.042*
C25	1.9760 (3)	0.37722 (6)	1.0943 (3)	0.0550 (5)
H25A	2.0660	0.3685	1.1933	0.083*
H25B	2.0295	0.3955	1.0474	0.083*
H25C	1.9288	0.3547	1.0267	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0262 (6)	0.0391 (6)	0.0304 (6)	−0.0010 (5)	0.0069 (5)	0.0018 (5)
O2	0.0396 (7)	0.0461 (7)	0.0365 (6)	0.0029 (5)	0.0229 (5)	0.0055 (5)
N1	0.0229 (7)	0.0311 (7)	0.0305 (7)	0.0021 (5)	0.0099 (5)	0.0082 (5)
N2	0.0206 (6)	0.0278 (6)	0.0359 (7)	0.0023 (5)	0.0121 (5)	0.0007 (5)
C1	0.0275 (8)	0.0286 (8)	0.0271 (7)	0.0093 (6)	0.0084 (6)	0.0047 (6)
C2	0.0442 (10)	0.0446 (10)	0.0330 (9)	0.0161 (8)	0.0164 (8)	0.0131 (7)
C3	0.0654 (13)	0.0466 (11)	0.0275 (8)	0.0204 (10)	0.0113 (9)	0.0077 (8)
C4	0.0525 (12)	0.0354 (9)	0.0321 (9)	0.0075 (8)	−0.0075 (8)	−0.0010 (7)
C5	0.0333 (9)	0.0291 (8)	0.0401 (9)	0.0025 (7)	−0.0001 (7)	0.0024 (7)
C6	0.0271 (8)	0.0216 (7)	0.0307 (8)	0.0058 (6)	0.0071 (6)	0.0013 (6)
C7	0.0248 (8)	0.0240 (7)	0.0300 (7)	−0.0013 (6)	0.0119 (6)	−0.0012 (6)
C8	0.0242 (8)	0.0260 (7)	0.0213 (7)	0.0034 (6)	0.0090 (6)	0.0018 (6)
C9	0.0225 (8)	0.0300 (8)	0.0250 (7)	0.0041 (6)	0.0115 (6)	0.0013 (6)
C10	0.0275 (9)	0.0382 (9)	0.0611 (11)	0.0025 (7)	0.0227 (8)	0.0008 (8)
C11	0.0305 (9)	0.0395 (9)	0.0488 (10)	−0.0003 (7)	0.0182 (8)	0.0147 (8)
C12	0.0282 (8)	0.0300 (8)	0.0262 (7)	0.0061 (6)	0.0111 (6)	0.0068 (6)
C13	0.0350 (9)	0.0324 (8)	0.0286 (8)	0.0109 (7)	0.0133 (7)	0.0076 (6)
C14	0.0301 (8)	0.0313 (8)	0.0286 (8)	0.0078 (6)	0.0115 (7)	0.0062 (6)
C15	0.0300 (8)	0.0331 (8)	0.0303 (8)	0.0081 (6)	0.0117 (7)	0.0064 (6)
C16	0.0277 (8)	0.0339 (8)	0.0288 (8)	0.0060 (6)	0.0108 (7)	0.0053 (6)
C17	0.0279 (8)	0.0327 (8)	0.0289 (8)	0.0051 (6)	0.0108 (7)	0.0042 (6)
C18	0.0275 (8)	0.0328 (8)	0.0312 (8)	0.0064 (6)	0.0118 (7)	0.0074 (6)
C19	0.0296 (9)	0.0327 (8)	0.0296 (8)	0.0063 (7)	0.0114 (7)	0.0043 (6)
C20	0.0301 (9)	0.0368 (9)	0.0330 (8)	0.0081 (7)	0.0138 (7)	0.0071 (7)
C21	0.0312 (9)	0.0366 (9)	0.0308 (8)	0.0079 (7)	0.0117 (7)	0.0041 (7)
C22	0.0300 (9)	0.0345 (8)	0.0323 (8)	0.0069 (7)	0.0130 (7)	0.0046 (7)
C23	0.0319 (9)	0.0343 (8)	0.0345 (8)	0.0079 (7)	0.0149 (7)	0.0051 (7)
C24	0.0284 (8)	0.0312 (8)	0.0399 (9)	0.0024 (7)	0.0091 (7)	0.0006 (7)
C25	0.0388 (11)	0.0557 (12)	0.0656 (13)	0.0178 (9)	0.0169 (10)	0.0056 (10)

Geometric parameters (Å, º) top

O1—C9	1.2208 (17)	C14—H14A	0.9700
O2—C7	1.2139 (18)	C14—H14B	0.9700
N1—C9	1.3618 (18)	C15—C16	1.520 (2)
N1—C1	1.4228 (19)	C15—H15A	0.9700
N1—C11	1.468 (2)	C15—H15B	0.9700
N2—C7	1.3666 (19)	C16—C17	1.520 (2)
N2—C6	1.421 (2)	C16—H16A	0.9700
N2—C10	1.467 (2)	C16—H16B	0.9700
C1—C2	1.395 (2)	C17—C18	1.525 (2)
C1—C6	1.395 (2)	C17—H17A	0.9700
C2—C3	1.379 (3)	C17—H17B	0.9700
C2—H2	0.9300	C18—C19	1.521 (2)
C3—C4	1.373 (3)	C18—H18A	0.9700
C3—H3	0.9300	C18—H18B	0.9700
C4—C5	1.381 (3)	C19—C20	1.523 (2)
C4—H4	0.9300	C19—H19A	0.9700
C5—C6	1.396 (2)	C19—H19B	0.9700
C5—H5	0.9300	C20—C21	1.519 (2)
C7—C8	1.528 (2)	C20—H20A	0.9700
C8—C9	1.522 (2)	C20—H20B	0.9700
C8—C12	1.5242 (19)	C21—C22	1.520 (2)
C8—H8	0.9800	C21—H21A	0.9700
C10—H10A	0.9600	C21—H21B	0.9700
C10—H10B	0.9600	C22—C23	1.522 (2)
C10—H10C	0.9600	C22—H22A	0.9700
C11—H11A	0.9600	C22—H22B	0.9700
C11—H11B	0.9600	C23—C24	1.516 (2)
C11—H11C	0.9600	C23—H23A	0.9700
C12—C13	1.520 (2)	C23—H23B	0.9700
C12—H12A	0.9700	C24—C25	1.517 (2)
C12—H12B	0.9700	C24—H24A	0.9700
C13—C14	1.5210 (19)	C24—H24B	0.9700
C13—H13A	0.9700	C25—H25A	0.9600
C13—H13B	0.9700	C25—H25B	0.9600
C14—C15	1.519 (2)	C25—H25C	0.9600

C9—N1—C1	122.79 (13)	C14—C15—C16	113.18 (13)
C9—N1—C11	118.43 (13)	C14—C15—H15A	108.9
C1—N1—C11	118.49 (12)	C16—C15—H15A	108.9
C7—N2—C6	123.17 (12)	C14—C15—H15B	108.9
C7—N2—C10	117.17 (13)	C16—C15—H15B	108.9
C6—N2—C10	119.21 (13)	H15A—C15—H15B	107.8
C2—C1—C6	119.69 (15)	C15—C16—C17	113.74 (13)
C2—C1—N1	118.38 (15)	C15—C16—H16A	108.8
C6—C1—N1	121.92 (13)	C17—C16—H16A	108.8
C3—C2—C1	120.69 (18)	C15—C16—H16B	108.8
C3—C2—H2	119.7	C17—C16—H16B	108.8
C1—C2—H2	119.7	H16A—C16—H16B	107.7
C4—C3—C2	119.84 (17)	C16—C17—C18	113.44 (13)
C4—C3—H3	120.1	C16—C17—H17A	108.9
C2—C3—H3	120.1	C18—C17—H17A	108.9
C3—C4—C5	120.19 (16)	C16—C17—H17B	108.9
C3—C4—H4	119.9	C18—C17—H17B	108.9
C5—C4—H4	119.9	H17A—C17—H17B	107.7
C4—C5—C6	120.97 (18)	C19—C18—C17	113.73 (13)
C4—C5—H5	119.5	C19—C18—H18A	108.8
C6—C5—H5	119.5	C17—C18—H18A	108.8
C1—C6—C5	118.59 (15)	C19—C18—H18B	108.8
C1—C6—N2	122.00 (13)	C17—C18—H18B	108.8
C5—C6—N2	119.39 (15)	H18A—C18—H18B	107.7
O2—C7—N2	121.93 (14)	C18—C19—C20	113.43 (13)
O2—C7—C8	122.37 (13)	C18—C19—H19A	108.9
N2—C7—C8	115.66 (12)	C20—C19—H19A	108.9
C9—C8—C12	111.82 (12)	C18—C19—H19B	108.9
C9—C8—C7	105.98 (11)	C20—C19—H19B	108.9
C12—C8—C7	111.95 (12)	H19A—C19—H19B	107.7
C9—C8—H8	109.0	C21—C20—C19	114.14 (13)
C12—C8—H8	109.0	C21—C20—H20A	108.7
C7—C8—H8	109.0	C19—C20—H20A	108.7
O1—C9—N1	121.58 (14)	C21—C20—H20B	108.7
O1—C9—C8	122.46 (13)	C19—C20—H20B	108.7
N1—C9—C8	115.90 (12)	H20A—C20—H20B	107.6
N2—C10—H10A	109.5	C20—C21—C22	113.48 (13)
N2—C10—H10B	109.5	C20—C21—H21A	108.9
H10A—C10—H10B	109.5	C22—C21—H21A	108.9
N2—C10—H10C	109.5	C20—C21—H21B	108.9
H10A—C10—H10C	109.5	C22—C21—H21B	108.9
H10B—C10—H10C	109.5	H21A—C21—H21B	107.7
N1—C11—H11A	109.5	C21—C22—C23	113.96 (13)
N1—C11—H11B	109.5	C21—C22—H22A	108.8
H11A—C11—H11B	109.5	C23—C22—H22A	108.8
N1—C11—H11C	109.5	C21—C22—H22B	108.8
H11A—C11—H11C	109.5	C23—C22—H22B	108.8
H11B—C11—H11C	109.5	H22A—C22—H22B	107.7
C13—C12—C8	112.92 (12)	C24—C23—C22	113.22 (13)
C13—C12—H12A	109.0	C24—C23—H23A	108.9
C8—C12—H12A	109.0	C22—C23—H23A	108.9
C13—C12—H12B	109.0	C24—C23—H23B	108.9
C8—C12—H12B	109.0	C22—C23—H23B	108.9
H12A—C12—H12B	107.8	H23A—C23—H23B	107.7
C12—C13—C14	113.18 (12)	C23—C24—C25	113.69 (15)
C12—C13—H13A	108.9	C23—C24—H24A	108.8
C14—C13—H13A	108.9	C25—C24—H24A	108.8
C12—C13—H13B	108.9	C23—C24—H24B	108.8
C14—C13—H13B	108.9	C25—C24—H24B	108.8
H13A—C13—H13B	107.8	H24A—C24—H24B	107.7
C15—C14—C13	113.74 (12)	C24—C25—H25A	109.5
C15—C14—H14A	108.8	C24—C25—H25B	109.5
C13—C14—H14A	108.8	H25A—C25—H25B	109.5
C15—C14—H14B	108.8	C24—C25—H25C	109.5
C13—C14—H14B	108.8	H25A—C25—H25C	109.5
H14A—C14—H14B	107.7	H25B—C25—H25C	109.5

C9—N1—C1—C2	−130.73 (16)	O2—C7—C8—C12	15.1 (2)
C11—N1—C1—C2	43.0 (2)	N2—C7—C8—C12	−167.19 (12)
C9—N1—C1—C6	50.6 (2)	C1—N1—C9—O1	177.20 (14)
C11—N1—C1—C6	−135.64 (15)	C11—N1—C9—O1	3.4 (2)
C6—C1—C2—C3	0.0 (2)	C1—N1—C9—C8	−5.7 (2)
N1—C1—C2—C3	−178.74 (15)	C11—N1—C9—C8	−179.47 (13)
C1—C2—C3—C4	1.1 (3)	C12—C8—C9—O1	−16.4 (2)
C2—C3—C4—C5	−0.9 (3)	C7—C8—C9—O1	105.85 (15)
C3—C4—C5—C6	−0.4 (3)	C12—C8—C9—N1	166.53 (12)
C2—C1—C6—C5	−1.2 (2)	C7—C8—C9—N1	−71.22 (15)
N1—C1—C6—C5	177.45 (13)	C9—C8—C12—C13	−67.67 (16)
C2—C1—C6—N2	−179.89 (14)	C7—C8—C12—C13	173.57 (13)
N1—C1—C6—N2	−1.2 (2)	C8—C12—C13—C14	174.38 (13)
C4—C5—C6—C1	1.4 (2)	C12—C13—C14—C15	−178.69 (14)
C4—C5—C6—N2	−179.87 (14)	C13—C14—C15—C16	178.98 (14)
C7—N2—C6—C1	−49.2 (2)	C14—C15—C16—C17	179.30 (14)
C10—N2—C6—C1	138.72 (15)	C15—C16—C17—C18	178.70 (13)
C7—N2—C6—C5	132.13 (15)	C16—C17—C18—C19	−179.64 (13)
C10—N2—C6—C5	−39.9 (2)	C17—C18—C19—C20	176.52 (13)
C6—N2—C7—O2	−176.13 (14)	C18—C19—C20—C21	−179.80 (14)
C10—N2—C7—O2	−3.9 (2)	C19—C20—C21—C22	175.23 (14)
C6—N2—C7—C8	6.2 (2)	C20—C21—C22—C23	179.33 (14)
C10—N2—C7—C8	178.37 (13)	C21—C22—C23—C24	174.57 (14)
O2—C7—C8—C9	−107.07 (15)	C22—C23—C24—C25	174.79 (15)
N2—C7—C8—C9	70.64 (15)

Experimental details

Crystal data
Chemical formula	C₂₅H₄₀N₂O₂
M_r	400.59
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	8.1286 (1), 33.5899 (5), 9.4095 (2)
β (°)	114.640 (1)
V (Å³)	2335.22 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.20 × 0.02 × 0.02

Data collection
Diffractometer	Bruker X8 APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	29471, 5359, 3671
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.139, 1.03
No. of reflections	5359
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.19

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
Dardouri, R., Ouazzani Chahdi, F., Saffon, N., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o2805. 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, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar