3-Hexadecyl-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/S1600536811013663

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1155

doi:10.1107/S1600536811013663

Open

access

3-Hexadecyl-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 ^a and Seik Weng Ng ^c ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, ^bService Commun Rayons-X, Laboratoire de Chimie de Coordination, Toulouse, France, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 6 April 2011; accepted 11 April 2011; online 16 April 2011)

In the title molecule, C₂₇H₄₄N₂O₂, the seven-membered ring adopts a boat-shaped conformation, with two C atoms of the fused benzene ring forming the stern and the methine C atom forming the prow. The hexadecyl substituent occupies an equatorial position, with the aliphatic chain exhibibiting an extended zigzag conformation.

Related literature

For the 3-tetradecyl-substituted analog, see: Dardouri et al. (2011 ).

Experimental

Crystal data

C₂₇H₄₄N₂O₂
M_r = 428.64
Monoclinic, P 2₁ /c
a = 8.1426 (1) Å
b = 36.2705 (5) Å
c = 9.4090 (1) Å
β = 114.611 (1)°
V = 2526.38 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.50 × 0.30 × 0.10 mm

Data collection

Bruker X8 APEXII diffractometer
45223 measured reflections
7353 independent reflections
5105 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.159
S = 1.03
7353 reflections
282 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.26 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/S1600536811013663/lh5231sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811013663/lh5231Isup2.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 a 3-substituted derivative. In a previous study, the compound was reacted with 1-bromotetradecane to give the tetradecyl substitued derivative (Dardouri et al., 2011). The corresponding hexdecyl title compound (Fig. 1) was obtained by using 1-bromohexadecane.

Related literature top

For the 3-tetradecyl-substituted analog, see: Dardouri et al. (2011).

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 (0.88 ml, 2.88 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.

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 C₂₇H₄₄N₂O₂ at the 50% probability level; hydrogen atoms are drawn as arbitrary radius.

3-Hexadecyl-1,5-dimethyl-1H-1,5-benzodiazepine- 2,4(3H,5H)-dione top

Crystal data top

C₂₇H₄₄N₂O₂	F(000) = 944
M_r = 428.64	D_x = 1.127 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9990 reflections
a = 8.1426 (1) Å	θ = 2.6–30.0°
b = 36.2705 (5) Å	µ = 0.07 mm⁻¹
c = 9.4090 (1) Å	T = 293 K
β = 114.611 (1)°	Plate, colorless
V = 2526.38 (5) Å³	0.50 × 0.30 × 0.10 mm
Z = 4

Data collection top

Bruker X8 APEXII diffractometer	5105 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.036
Graphite monochromator	θ_max = 30.0°, θ_min = 2.5°
ϕ and ω scans	h = −10→11
45223 measured reflections	k = −50→51
7353 independent reflections	l = −12→13

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0871P)² + 0.3018P] where P = (F_o² + 2F_c²)/3
7353 reflections	(Δ/σ)_max = 0.001
282 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₇H₄₄N₂O₂	V = 2526.38 (5) Å³
M_r = 428.64	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1426 (1) Å	µ = 0.07 mm⁻¹
b = 36.2705 (5) Å	T = 293 K
c = 9.4090 (1) Å	0.50 × 0.30 × 0.10 mm
β = 114.611 (1)°

Data collection top

Bruker X8 APEXII diffractometer	5105 reflections with I > 2σ(I)
45223 measured reflections	R_int = 0.036
7353 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 1.03	Δρ_max = 0.34 e Å⁻³
7353 reflections	Δρ_min = −0.26 e Å⁻³
282 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.02825 (12)	0.20901 (2)	0.37201 (10)	0.0323 (2)
O2	−0.39162 (13)	0.17141 (3)	0.40983 (10)	0.0376 (2)
N1	−0.19184 (13)	0.22225 (3)	0.13447 (11)	0.0271 (2)
N2	−0.51023 (13)	0.19449 (3)	0.16414 (12)	0.0268 (2)
C1	−0.35060 (17)	0.21187 (3)	0.00186 (14)	0.0273 (3)
C2	−0.3522 (2)	0.21567 (4)	−0.14654 (15)	0.0400 (3)
H2	−0.2498	0.2243	−0.1560	0.048*
C3	−0.5039 (2)	0.20671 (4)	−0.27923 (16)	0.0491 (4)
H3	−0.5028	0.2088	−0.3773	0.059*
C4	−0.6573 (2)	0.19462 (4)	−0.26542 (17)	0.0485 (4)
H4	−0.7606	0.1891	−0.3546	0.058*
C5	−0.65797 (19)	0.19072 (3)	−0.11957 (16)	0.0384 (3)
H5	−0.7621	0.1825	−0.1117	0.046*
C6	−0.50464 (16)	0.19891 (3)	0.01618 (14)	0.0267 (3)
C7	−0.67424 (18)	0.20524 (4)	0.18255 (19)	0.0388 (3)
H7A	−0.6415	0.2151	0.2855	0.058*
H7B	−0.7501	0.1840	0.1681	0.058*
H7C	−0.7383	0.2236	0.1061	0.058*
C8	−0.37885 (16)	0.17653 (3)	0.28661 (13)	0.0249 (2)
C9	−0.21270 (15)	0.16463 (3)	0.26138 (13)	0.0233 (2)
H9A	−0.2522	0.1529	0.1587	0.028*
C10	−0.11159 (16)	0.20013 (3)	0.26219 (13)	0.0237 (2)
C11	−0.09947 (19)	0.25653 (4)	0.12803 (18)	0.0384 (3)
H11A	−0.0195	0.2638	0.2321	0.058*
H11B	−0.1873	0.2756	0.0806	0.058*
H11C	−0.0312	0.2526	0.0672	0.058*
C12	−0.09467 (16)	0.13780 (3)	0.38687 (13)	0.0268 (3)
H12A	−0.1690	0.1176	0.3940	0.032*
H12B	−0.0452	0.1504	0.4870	0.032*
C13	0.06032 (17)	0.12220 (3)	0.35425 (14)	0.0304 (3)
H13A	0.0108	0.1073	0.2601	0.036*
H13B	0.1266	0.1424	0.3354	0.036*
C14	0.19019 (17)	0.09876 (3)	0.48780 (14)	0.0279 (3)
H14A	0.1243	0.0782	0.5046	0.034*
H14B	0.2367	0.1134	0.5826	0.034*
C15	0.34868 (17)	0.08387 (3)	0.45879 (14)	0.0295 (3)
H15A	0.3025	0.0687	0.3655	0.035*
H15B	0.4133	0.1044	0.4398	0.035*
C16	0.47967 (16)	0.06121 (3)	0.59449 (14)	0.0283 (3)
H16A	0.4146	0.0409	0.6139	0.034*
H16B	0.5262	0.0765	0.6875	0.034*
C17	0.63784 (16)	0.04591 (3)	0.56685 (14)	0.0278 (3)
H17A	0.7022	0.0662	0.5462	0.033*
H17B	0.5914	0.0304	0.4746	0.033*
C18	0.77024 (16)	0.02355 (3)	0.70403 (14)	0.0278 (3)
H18A	0.8161	0.0390	0.7964	0.033*
H18B	0.7060	0.0031	0.7243	0.033*
C19	0.92947 (16)	0.00835 (3)	0.67688 (14)	0.0277 (3)
H19A	0.8839	−0.0079	0.5869	0.033*
H19B	0.9910	0.0287	0.6527	0.033*
C20	1.06521 (16)	−0.01274 (3)	0.81635 (14)	0.0292 (3)
H20A	1.1111	0.0036	0.9062	0.035*
H20B	1.0035	−0.0330	0.8408	0.035*
C21	1.22377 (17)	−0.02808 (3)	0.78946 (14)	0.0297 (3)
H21A	1.2842	−0.0079	0.7631	0.036*
H21B	1.1782	−0.0448	0.7009	0.036*
C22	1.36085 (17)	−0.04850 (4)	0.93023 (15)	0.0319 (3)
H22A	1.3000	−0.0685	0.9571	0.038*
H22B	1.4070	−0.0317	1.0185	0.038*
C23	1.51950 (17)	−0.06420 (4)	0.90372 (14)	0.0317 (3)
H23A	1.5760	−0.0445	0.8706	0.038*
H23B	1.4744	−0.0822	0.8199	0.038*
C24	1.66148 (17)	−0.08248 (3)	1.04886 (14)	0.0309 (3)
H24A	1.7070	−0.0644	1.1323	0.037*
H24B	1.6045	−0.1020	1.0824	0.037*
C25	1.81995 (17)	−0.09856 (4)	1.02357 (15)	0.0318 (3)
H25A	1.7764	−0.1184	0.9479	0.038*
H25B	1.8696	−0.0796	0.9800	0.038*
C26	1.96936 (17)	−0.11326 (3)	1.17273 (15)	0.0331 (3)
H26A	2.0196	−0.0929	1.2450	0.040*
H26B	1.9174	−0.1306	1.2210	0.040*
C27	2.1211 (2)	−0.13226 (5)	1.1471 (2)	0.0527 (4)
H27A	2.2105	−0.1408	1.2454	0.079*
H27B	2.1755	−0.1151	1.1017	0.079*
H27C	2.0733	−0.1528	1.0778	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0250 (5)	0.0383 (5)	0.0285 (5)	−0.0006 (4)	0.0060 (4)	0.0013 (4)
O2	0.0388 (6)	0.0456 (5)	0.0359 (5)	0.0037 (4)	0.0231 (4)	0.0053 (4)
N1	0.0210 (5)	0.0307 (5)	0.0285 (5)	0.0020 (4)	0.0092 (4)	0.0081 (4)
N2	0.0197 (5)	0.0258 (5)	0.0348 (5)	0.0031 (4)	0.0112 (4)	0.0009 (4)
C1	0.0275 (6)	0.0265 (6)	0.0246 (5)	0.0091 (5)	0.0074 (5)	0.0048 (4)
C2	0.0447 (8)	0.0452 (8)	0.0309 (7)	0.0174 (6)	0.0166 (6)	0.0137 (6)
C3	0.0656 (11)	0.0486 (9)	0.0249 (7)	0.0224 (8)	0.0106 (7)	0.0087 (6)
C4	0.0545 (10)	0.0342 (7)	0.0314 (7)	0.0090 (7)	−0.0074 (7)	−0.0003 (6)
C5	0.0319 (7)	0.0271 (6)	0.0408 (7)	0.0028 (5)	0.0000 (6)	0.0011 (5)
C6	0.0249 (6)	0.0203 (5)	0.0288 (6)	0.0065 (4)	0.0052 (5)	0.0019 (4)
C7	0.0238 (7)	0.0365 (7)	0.0601 (9)	0.0034 (5)	0.0215 (7)	0.0009 (6)
C8	0.0238 (6)	0.0231 (5)	0.0279 (6)	−0.0004 (4)	0.0110 (5)	−0.0012 (4)
C9	0.0223 (6)	0.0246 (5)	0.0216 (5)	0.0048 (4)	0.0080 (4)	0.0023 (4)
C10	0.0220 (6)	0.0276 (5)	0.0236 (5)	0.0057 (4)	0.0116 (5)	0.0027 (4)
C11	0.0294 (7)	0.0373 (7)	0.0492 (8)	−0.0004 (5)	0.0171 (6)	0.0144 (6)
C12	0.0269 (6)	0.0282 (6)	0.0248 (5)	0.0070 (5)	0.0102 (5)	0.0076 (4)
C13	0.0315 (7)	0.0328 (6)	0.0271 (6)	0.0122 (5)	0.0125 (5)	0.0085 (5)
C14	0.0280 (6)	0.0282 (6)	0.0273 (6)	0.0082 (5)	0.0111 (5)	0.0059 (5)
C15	0.0283 (7)	0.0311 (6)	0.0292 (6)	0.0088 (5)	0.0120 (5)	0.0067 (5)
C16	0.0247 (6)	0.0318 (6)	0.0274 (6)	0.0073 (5)	0.0098 (5)	0.0049 (5)
C17	0.0244 (6)	0.0303 (6)	0.0275 (6)	0.0067 (5)	0.0097 (5)	0.0042 (5)
C18	0.0248 (6)	0.0297 (6)	0.0289 (6)	0.0060 (5)	0.0111 (5)	0.0054 (5)
C19	0.0247 (6)	0.0295 (6)	0.0283 (6)	0.0070 (5)	0.0103 (5)	0.0037 (5)
C20	0.0254 (6)	0.0327 (6)	0.0294 (6)	0.0069 (5)	0.0113 (5)	0.0067 (5)
C21	0.0269 (6)	0.0341 (6)	0.0280 (6)	0.0081 (5)	0.0113 (5)	0.0055 (5)
C22	0.0274 (7)	0.0370 (7)	0.0319 (6)	0.0096 (5)	0.0128 (5)	0.0077 (5)
C23	0.0284 (7)	0.0367 (6)	0.0303 (6)	0.0103 (5)	0.0124 (5)	0.0062 (5)
C24	0.0281 (7)	0.0342 (6)	0.0306 (6)	0.0084 (5)	0.0124 (5)	0.0048 (5)
C25	0.0291 (7)	0.0332 (6)	0.0341 (6)	0.0090 (5)	0.0140 (6)	0.0044 (5)
C26	0.0275 (7)	0.0293 (6)	0.0374 (7)	0.0039 (5)	0.0083 (6)	0.0017 (5)
C27	0.0346 (8)	0.0525 (9)	0.0647 (10)	0.0169 (7)	0.0145 (8)	0.0033 (8)

Geometric parameters (Å, º) top

O1—C10	1.2197 (14)	C15—H15A	0.9700
O2—C8	1.2206 (14)	C15—H15B	0.9700
N1—C10	1.3640 (14)	C16—C17	1.5209 (16)
N1—C1	1.4235 (16)	C16—H16A	0.9700
N1—C11	1.4676 (16)	C16—H16B	0.9700
N2—C8	1.3676 (15)	C17—C18	1.5254 (16)
N2—C6	1.4208 (15)	C17—H17A	0.9700
N2—C7	1.4690 (16)	C17—H17B	0.9700
C1—C6	1.3975 (18)	C18—C19	1.5252 (16)
C1—C2	1.3976 (17)	C18—H18A	0.9700
C2—C3	1.380 (2)	C18—H18B	0.9700
C2—H2	0.9300	C19—C20	1.5233 (16)
C3—C4	1.380 (2)	C19—H19A	0.9700
C3—H3	0.9300	C19—H19B	0.9700
C4—C5	1.382 (2)	C20—C21	1.5207 (16)
C4—H4	0.9300	C20—H20A	0.9700
C5—C6	1.3964 (18)	C20—H20B	0.9700
C5—H5	0.9300	C21—C22	1.5223 (17)
C7—H7A	0.9600	C21—H21A	0.9700
C7—H7B	0.9600	C21—H21B	0.9700
C7—H7C	0.9600	C22—C23	1.5244 (17)
C8—C9	1.5298 (16)	C22—H22A	0.9700
C9—C12	1.5230 (15)	C22—H22B	0.9700
C9—C10	1.5266 (16)	C23—C24	1.5251 (17)
C9—H9A	0.9800	C23—H23A	0.9700
C11—H11A	0.9600	C23—H23B	0.9700
C11—H11B	0.9600	C24—C25	1.5222 (17)
C11—H11C	0.9600	C24—H24A	0.9700
C12—C13	1.5264 (16)	C24—H24B	0.9700
C12—H12A	0.9700	C25—C26	1.5205 (17)
C12—H12B	0.9700	C25—H25A	0.9700
C13—C14	1.5210 (16)	C25—H25B	0.9700
C13—H13A	0.9700	C26—C27	1.5196 (19)
C13—H13B	0.9700	C26—H26A	0.9700
C14—C15	1.5248 (16)	C26—H26B	0.9700
C14—H14A	0.9700	C27—H27A	0.9600
C14—H14B	0.9700	C27—H27B	0.9600
C15—C16	1.5195 (16)	C27—H27C	0.9600

C10—N1—C1	122.93 (10)	C15—C16—C17	113.69 (10)
C10—N1—C11	117.97 (10)	C15—C16—H16A	108.8
C1—N1—C11	118.81 (10)	C17—C16—H16A	108.8
C8—N2—C6	123.12 (10)	C15—C16—H16B	108.8
C8—N2—C7	117.24 (10)	C17—C16—H16B	108.8
C6—N2—C7	119.16 (10)	H16A—C16—H16B	107.7
C6—C1—C2	119.60 (12)	C16—C17—C18	113.56 (10)
C6—C1—N1	121.90 (10)	C16—C17—H17A	108.9
C2—C1—N1	118.48 (12)	C18—C17—H17A	108.9
C3—C2—C1	120.87 (15)	C16—C17—H17B	108.9
C3—C2—H2	119.6	C18—C17—H17B	108.9
C1—C2—H2	119.6	H17A—C17—H17B	107.7
C4—C3—C2	119.58 (14)	C19—C18—C17	113.64 (10)
C4—C3—H3	120.2	C19—C18—H18A	108.8
C2—C3—H3	120.2	C17—C18—H18A	108.8
C3—C4—C5	120.28 (14)	C19—C18—H18B	108.8
C3—C4—H4	119.9	C17—C18—H18B	108.8
C5—C4—H4	119.9	H18A—C18—H18B	107.7
C4—C5—C6	120.98 (14)	C20—C19—C18	113.56 (10)
C4—C5—H5	119.5	C20—C19—H19A	108.9
C6—C5—H5	119.5	C18—C19—H19A	108.9
C5—C6—C1	118.67 (12)	C20—C19—H19B	108.9
C5—C6—N2	119.41 (12)	C18—C19—H19B	108.9
C1—C6—N2	121.91 (11)	H19A—C19—H19B	107.7
N2—C7—H7A	109.5	C21—C20—C19	113.71 (10)
N2—C7—H7B	109.5	C21—C20—H20A	108.8
H7A—C7—H7B	109.5	C19—C20—H20A	108.8
N2—C7—H7C	109.5	C21—C20—H20B	108.8
H7A—C7—H7C	109.5	C19—C20—H20B	108.8
H7B—C7—H7C	109.5	H20A—C20—H20B	107.7
O2—C8—N2	121.78 (11)	C20—C21—C22	113.51 (10)
O2—C8—C9	122.36 (11)	C20—C21—H21A	108.9
N2—C8—C9	115.83 (10)	C22—C21—H21A	108.9
C12—C9—C10	111.73 (10)	C20—C21—H21B	108.9
C12—C9—C8	111.91 (9)	C22—C21—H21B	108.9
C10—C9—C8	105.74 (9)	H21A—C21—H21B	107.7
C12—C9—H9A	109.1	C21—C22—C23	113.81 (10)
C10—C9—H9A	109.1	C21—C22—H22A	108.8
C8—C9—H9A	109.1	C23—C22—H22A	108.8
O1—C10—N1	121.80 (11)	C21—C22—H22B	108.8
O1—C10—C9	122.55 (10)	C23—C22—H22B	108.8
N1—C10—C9	115.60 (10)	H22A—C22—H22B	107.7
N1—C11—H11A	109.5	C22—C23—C24	113.20 (10)
N1—C11—H11B	109.5	C22—C23—H23A	108.9
H11A—C11—H11B	109.5	C24—C23—H23A	108.9
N1—C11—H11C	109.5	C22—C23—H23B	108.9
H11A—C11—H11C	109.5	C24—C23—H23B	108.9
H11B—C11—H11C	109.5	H23A—C23—H23B	107.8
C9—C12—C13	112.87 (9)	C25—C24—C23	113.73 (10)
C9—C12—H12A	109.0	C25—C24—H24A	108.8
C13—C12—H12A	109.0	C23—C24—H24A	108.8
C9—C12—H12B	109.0	C25—C24—H24B	108.8
C13—C12—H12B	109.0	C23—C24—H24B	108.8
H12A—C12—H12B	107.8	H24A—C24—H24B	107.7
C14—C13—C12	112.94 (9)	C26—C25—C24	113.24 (10)
C14—C13—H13A	109.0	C26—C25—H25A	108.9
C12—C13—H13A	109.0	C24—C25—H25A	108.9
C14—C13—H13B	109.0	C26—C25—H25B	108.9
C12—C13—H13B	109.0	C24—C25—H25B	108.9
H13A—C13—H13B	107.8	H25A—C25—H25B	107.7
C13—C14—C15	113.52 (10)	C27—C26—C25	113.80 (12)
C13—C14—H14A	108.9	C27—C26—H26A	108.8
C15—C14—H14A	108.9	C25—C26—H26A	108.8
C13—C14—H14B	108.9	C27—C26—H26B	108.8
C15—C14—H14B	108.9	C25—C26—H26B	108.8
H14A—C14—H14B	107.7	H26A—C26—H26B	107.7
C16—C15—C14	113.04 (10)	C26—C27—H27A	109.5
C16—C15—H15A	109.0	C26—C27—H27B	109.5
C14—C15—H15A	109.0	H27A—C27—H27B	109.5
C16—C15—H15B	109.0	C26—C27—H27C	109.5
C14—C15—H15B	109.0	H27A—C27—H27C	109.5
H15A—C15—H15B	107.8	H27B—C27—H27C	109.5

C10—N1—C1—C6	50.83 (16)	N2—C8—C9—C10	70.80 (12)
C11—N1—C1—C6	−135.46 (12)	C1—N1—C10—O1	177.18 (11)
C10—N1—C1—C2	−130.67 (12)	C11—N1—C10—O1	3.42 (17)
C11—N1—C1—C2	43.04 (16)	C1—N1—C10—C9	−5.49 (16)
C6—C1—C2—C3	−0.15 (19)	C11—N1—C10—C9	−179.24 (10)
N1—C1—C2—C3	−178.69 (12)	C12—C9—C10—O1	−16.10 (15)
C1—C2—C3—C4	1.4 (2)	C8—C9—C10—O1	105.89 (12)
C2—C3—C4—C5	−1.4 (2)	C12—C9—C10—N1	166.59 (9)
C3—C4—C5—C6	0.0 (2)	C8—C9—C10—N1	−71.43 (12)
C4—C5—C6—C1	1.23 (18)	C10—C9—C12—C13	−68.09 (13)
C4—C5—C6—N2	−179.85 (11)	C8—C9—C12—C13	173.55 (10)
C2—C1—C6—C5	−1.16 (17)	C9—C12—C13—C14	173.66 (10)
N1—C1—C6—C5	177.32 (11)	C12—C13—C14—C15	−178.37 (10)
C2—C1—C6—N2	179.94 (11)	C13—C14—C15—C16	178.71 (11)
N1—C1—C6—N2	−1.57 (17)	C14—C15—C16—C17	179.55 (10)
C8—N2—C6—C5	132.06 (12)	C15—C16—C17—C18	179.34 (10)
C7—N2—C6—C5	−39.70 (15)	C16—C17—C18—C19	−179.70 (10)
C8—N2—C6—C1	−49.05 (16)	C17—C18—C19—C20	177.81 (10)
C7—N2—C6—C1	139.19 (12)	C18—C19—C20—C21	179.76 (10)
C6—N2—C8—O2	−176.04 (11)	C19—C20—C21—C22	178.91 (11)
C7—N2—C8—O2	−4.13 (17)	C20—C21—C22—C23	179.57 (11)
C6—N2—C8—C9	6.17 (15)	C21—C22—C23—C24	176.41 (11)
C7—N2—C8—C9	178.07 (10)	C22—C23—C24—C25	179.53 (11)
O2—C8—C9—C12	14.88 (16)	C23—C24—C25—C26	174.22 (11)
N2—C8—C9—C12	−167.34 (10)	C24—C25—C26—C27	175.17 (12)
O2—C8—C9—C10	−106.98 (12)

Experimental details

Crystal data
Chemical formula	C₂₇H₄₄N₂O₂
M_r	428.64
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.1426 (1), 36.2705 (5), 9.4090 (1)
β (°)	114.611 (1)
V (Å³)	2526.38 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.50 × 0.30 × 0.10

Data collection
Diffractometer	Bruker X8 APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	45223, 7353, 5105
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.159, 1.03
No. of reflections	7353
No. of parameters	282
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.26

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. (2011). Acta Cryst. E67, o674. 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