3-Allyl-1,5-dibenzyl-1,5-benzodiazepine-2,4-dione

Jabli, H.; Kandri Rodi, Y.; Saffon, N.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S160053680904851X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3150

doi:10.1107/S160053680904851X

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3-Allyl-1,5-dibenzyl-1,5-benzodiazepine-2,4-dione

Hind Jabli,^a Y. Kandri Rodi,^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, 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, C₂₆H₂₄N₂O₂, features a benzene ring fused with a seven-membered diazepine ring; the latter ring adopts a boat conformation (with the allyldimethylaminomethyl-bearing C atom as the prow and the fused-ring C atoms as the stern).

Related literature

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

Experimental

Crystal data

C₂₆H₂₄N₂O₂
M_r = 396.47
Monoclinic, P 2₁ /c
a = 9.2603 (4) Å
b = 14.0037 (6) Å
c = 16.2249 (7) Å
β = 91.996 (1)°
V = 2102.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 193 K
0.40 × 0.40 × 0.07 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: none
27620 measured reflections
4820 independent reflections
2934 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.117
S = 1.00
4820 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.18 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/S160053680904851X/sj2680sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680904851X/sj2680Isup2.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 allyl 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.

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 C₂₆H₂₄N₂O₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

3-Allyl-1,5-dibenzyl-1,5-benzodiazepine-2,4-dione top

Crystal data top

C₂₆H₂₄N₂O₂	F(000) = 840
M_r = 396.47	D_x = 1.252 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4269 reflections
a = 9.2603 (4) Å	θ = 2.5–25.0°
b = 14.0037 (6) Å	µ = 0.08 mm⁻¹
c = 16.2249 (7) Å	T = 193 K
β = 91.996 (1)°	Plate, colorless
V = 2102.7 (2) Å³	0.40 × 0.40 × 0.07 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	2934 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.050
Graphite monochromator	θ_max = 27.5°, θ_min = 1.9°
ϕ and ω scans	h = −11→12
27620 measured reflections	k = −18→18
4820 independent reflections	l = −21→16

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0487P)² + 0.414P] where P = (F_o² + 2F_c²)/3
4820 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₆H₂₄N₂O₂	V = 2102.7 (2) Å³
M_r = 396.47	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.2603 (4) Å	µ = 0.08 mm⁻¹
b = 14.0037 (6) Å	T = 193 K
c = 16.2249 (7) Å	0.40 × 0.40 × 0.07 mm
β = 91.996 (1)°

Data collection top

Bruker APEXII diffractometer	2934 reflections with I > 2σ(I)
27620 measured reflections	R_int = 0.050
4820 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.00	Δρ_max = 0.21 e Å⁻³
4820 reflections	Δρ_min = −0.18 e Å⁻³
271 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.49018 (14)	0.26136 (9)	0.33899 (7)	0.0470 (3)
O2	0.33507 (16)	0.40157 (8)	0.16934 (7)	0.0498 (4)
N1	0.50477 (15)	0.15481 (9)	0.23332 (8)	0.0330 (3)
N2	0.37563 (15)	0.26484 (9)	0.09974 (7)	0.0320 (3)
C1	0.43555 (19)	0.22301 (11)	0.27747 (10)	0.0348 (4)
C2	0.33193 (19)	0.31439 (11)	0.16711 (9)	0.0350 (4)
C3	0.28998 (18)	0.25375 (11)	0.24091 (9)	0.0336 (4)
H3	0.2349	0.1963	0.2210	0.040*
C4	0.2006 (2)	0.30886 (12)	0.30184 (10)	0.0409 (4)
H4A	0.1979	0.2725	0.3541	0.049*
H4B	0.2479	0.3709	0.3139	0.049*
C5	0.0492 (2)	0.32639 (13)	0.27024 (11)	0.0485 (5)
H5	0.0365	0.3419	0.2135	0.058*
C6	−0.0667 (3)	0.32235 (16)	0.31310 (14)	0.0658 (6)
H6A	−0.0595	0.3071	0.3701	0.079*
H6B	−0.1585	0.3347	0.2874	0.079*
C7	0.43855 (17)	0.10939 (11)	0.16252 (9)	0.0294 (3)
C8	0.37894 (16)	0.16300 (10)	0.09694 (9)	0.0285 (3)
C9	0.32362 (17)	0.11561 (12)	0.02736 (9)	0.0332 (4)
H9	0.2852	0.1515	−0.0180	0.040*
C10	0.32381 (18)	0.01744 (12)	0.02331 (10)	0.0371 (4)
H10	0.2853	−0.0140	−0.0245	0.045*
C11	0.38017 (18)	−0.03554 (12)	0.08892 (10)	0.0361 (4)
H11	0.3788	−0.1033	0.0866	0.043*
C12	0.43813 (17)	0.01011 (11)	0.15748 (10)	0.0331 (4)
H12	0.4784	−0.0265	0.2019	0.040*
C13	0.65246 (19)	0.12564 (13)	0.25940 (10)	0.0407 (4)
H13A	0.6512	0.0580	0.2772	0.049*
H13B	0.6853	0.1648	0.3073	0.049*
C14	0.75779 (18)	0.13696 (12)	0.19117 (10)	0.0382 (4)
C15	0.7462 (2)	0.21035 (14)	0.13427 (12)	0.0483 (5)
H15	0.6699	0.2554	0.1376	0.058*
C16	0.8450 (2)	0.21874 (16)	0.07231 (13)	0.0603 (6)
H16	0.8353	0.2689	0.0331	0.072*
C17	0.9570 (2)	0.15453 (16)	0.06759 (14)	0.0606 (6)
H17	1.0243	0.1602	0.0250	0.073*
C18	0.9714 (2)	0.08237 (15)	0.12436 (14)	0.0564 (5)
H18	1.0498	0.0389	0.1218	0.068*
C19	0.8714 (2)	0.07300 (13)	0.18536 (12)	0.0459 (5)
H19	0.8808	0.0220	0.2238	0.055*
C20	0.4289 (2)	0.32016 (12)	0.02996 (10)	0.0380 (4)
H20A	0.4780	0.2757	−0.0073	0.046*
H20B	0.5023	0.3659	0.0516	0.046*
C21	0.3168 (2)	0.37497 (12)	−0.02019 (9)	0.0385 (4)
C22	0.3657 (3)	0.43780 (13)	−0.07970 (11)	0.0553 (5)
H22	0.4664	0.4466	−0.0858	0.066*
C23	0.2682 (4)	0.48731 (17)	−0.12977 (13)	0.0764 (8)
H23	0.3021	0.5301	−0.1702	0.092*
C24	0.1224 (4)	0.47491 (18)	−0.12138 (15)	0.0839 (9)
H24	0.0558	0.5084	−0.1566	0.101*
C25	0.0723 (3)	0.41385 (16)	−0.06193 (15)	0.0704 (7)
H25	−0.0286	0.4058	−0.0557	0.084*
C26	0.1706 (2)	0.36411 (13)	−0.01120 (11)	0.0487 (5)
H26	0.1363	0.3224	0.0299	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0684 (9)	0.0398 (7)	0.0320 (6)	−0.0053 (6)	−0.0109 (6)	−0.0058 (5)
O2	0.0876 (10)	0.0251 (7)	0.0365 (7)	−0.0007 (6)	0.0008 (7)	−0.0003 (5)
N1	0.0420 (8)	0.0286 (7)	0.0280 (7)	−0.0001 (6)	−0.0064 (6)	0.0014 (6)
N2	0.0451 (8)	0.0256 (7)	0.0254 (7)	0.0015 (6)	0.0000 (6)	0.0024 (5)
C1	0.0534 (11)	0.0253 (8)	0.0255 (8)	−0.0046 (8)	−0.0026 (7)	0.0035 (7)
C2	0.0494 (11)	0.0275 (9)	0.0277 (8)	0.0007 (8)	−0.0044 (7)	0.0003 (7)
C3	0.0496 (10)	0.0258 (8)	0.0251 (8)	0.0005 (7)	−0.0003 (7)	−0.0025 (6)
C4	0.0616 (12)	0.0328 (9)	0.0283 (9)	0.0048 (9)	0.0038 (8)	−0.0028 (7)
C5	0.0664 (14)	0.0411 (11)	0.0381 (10)	0.0129 (10)	0.0013 (9)	−0.0056 (8)
C6	0.0641 (15)	0.0742 (16)	0.0593 (13)	−0.0053 (12)	0.0039 (11)	−0.0084 (12)
C7	0.0322 (9)	0.0282 (8)	0.0277 (8)	−0.0006 (7)	0.0018 (7)	−0.0014 (6)
C8	0.0338 (9)	0.0250 (8)	0.0268 (8)	0.0005 (7)	0.0042 (7)	−0.0010 (6)
C9	0.0353 (9)	0.0374 (10)	0.0267 (8)	0.0040 (7)	−0.0012 (7)	−0.0031 (7)
C10	0.0361 (10)	0.0390 (10)	0.0363 (9)	−0.0002 (8)	0.0008 (7)	−0.0131 (8)
C11	0.0394 (10)	0.0270 (8)	0.0425 (10)	0.0000 (7)	0.0090 (8)	−0.0064 (7)
C12	0.0365 (9)	0.0287 (9)	0.0343 (9)	0.0029 (7)	0.0040 (7)	0.0029 (7)
C13	0.0466 (11)	0.0368 (10)	0.0379 (9)	0.0003 (8)	−0.0112 (8)	0.0053 (8)
C14	0.0378 (10)	0.0328 (9)	0.0430 (10)	−0.0051 (8)	−0.0135 (8)	0.0008 (8)
C15	0.0398 (11)	0.0435 (11)	0.0613 (12)	−0.0011 (9)	−0.0048 (9)	0.0144 (9)
C16	0.0472 (12)	0.0683 (15)	0.0654 (14)	−0.0086 (11)	0.0005 (10)	0.0253 (11)
C17	0.0401 (12)	0.0711 (15)	0.0707 (14)	−0.0050 (11)	0.0047 (10)	0.0036 (12)
C18	0.0400 (11)	0.0509 (13)	0.0779 (15)	0.0021 (9)	−0.0041 (11)	−0.0037 (11)
C19	0.0426 (11)	0.0368 (10)	0.0572 (12)	−0.0012 (9)	−0.0127 (9)	0.0023 (9)
C20	0.0502 (11)	0.0339 (9)	0.0302 (8)	−0.0051 (8)	0.0038 (8)	0.0057 (7)
C21	0.0631 (13)	0.0280 (9)	0.0243 (8)	0.0036 (8)	−0.0005 (8)	−0.0006 (7)
C22	0.0937 (16)	0.0383 (11)	0.0345 (10)	0.0081 (11)	0.0103 (10)	0.0069 (8)
C23	0.141 (3)	0.0484 (14)	0.0396 (12)	0.0187 (16)	0.0015 (14)	0.0142 (10)
C24	0.132 (3)	0.0580 (16)	0.0587 (15)	0.0313 (17)	−0.0366 (17)	0.0071 (12)
C25	0.0779 (16)	0.0554 (14)	0.0756 (16)	0.0177 (12)	−0.0285 (13)	−0.0023 (12)
C26	0.0633 (14)	0.0394 (11)	0.0425 (10)	0.0056 (10)	−0.0105 (9)	0.0016 (8)

Geometric parameters (Å, º) top

O1—C1	1.2271 (19)	C13—C14	1.509 (2)
O2—C2	1.2216 (19)	C13—H13A	0.9900
N1—C1	1.367 (2)	C13—H13B	0.9900
N1—C7	1.4321 (19)	C14—C15	1.383 (2)
N1—C13	1.475 (2)	C14—C19	1.388 (2)
N2—C2	1.3678 (19)	C15—C16	1.388 (3)
N2—C8	1.4273 (19)	C15—H15	0.9500
N2—C20	1.4710 (19)	C16—C17	1.377 (3)
C1—C3	1.516 (2)	C16—H16	0.9500
C2—C3	1.529 (2)	C17—C18	1.371 (3)
C3—C4	1.521 (2)	C17—H17	0.9500
C3—H3	1.0000	C18—C19	1.385 (3)
C4—C5	1.496 (3)	C18—H18	0.9500
C4—H4A	0.9900	C19—H19	0.9500
C4—H4B	0.9900	C20—C21	1.506 (2)
C5—C6	1.300 (3)	C20—H20A	0.9900
C5—H5	0.9500	C20—H20B	0.9900
C6—H6A	0.9500	C21—C26	1.376 (3)
C6—H6B	0.9500	C21—C22	1.393 (2)
C7—C12	1.393 (2)	C22—C23	1.380 (3)
C7—C8	1.400 (2)	C22—H22	0.9500
C8—C9	1.392 (2)	C23—C24	1.372 (4)
C9—C10	1.376 (2)	C23—H23	0.9500
C9—H9	0.9500	C24—C25	1.381 (4)
C10—C11	1.385 (2)	C24—H24	0.9500
C10—H10	0.9500	C25—C26	1.392 (3)
C11—C12	1.376 (2)	C25—H25	0.9500
C11—H11	0.9500	C26—H26	0.9500
C12—H12	0.9500

C1—N1—C7	122.36 (14)	N1—C13—C14	112.15 (13)
C1—N1—C13	119.35 (13)	N1—C13—H13A	109.2
C7—N1—C13	118.29 (13)	C14—C13—H13A	109.2
C2—N2—C8	122.66 (13)	N1—C13—H13B	109.2
C2—N2—C20	117.67 (13)	C14—C13—H13B	109.2
C8—N2—C20	119.58 (12)	H13A—C13—H13B	107.9
O1—C1—N1	123.00 (16)	C15—C14—C19	118.41 (17)
O1—C1—C3	121.99 (15)	C15—C14—C13	122.04 (16)
N1—C1—C3	114.85 (13)	C19—C14—C13	119.55 (16)
O2—C2—N2	121.55 (15)	C14—C15—C16	120.56 (18)
O2—C2—C3	122.56 (14)	C14—C15—H15	119.7
N2—C2—C3	115.74 (13)	C16—C15—H15	119.7
C1—C3—C4	112.72 (13)	C17—C16—C15	120.13 (19)
C1—C3—C2	102.56 (13)	C17—C16—H16	119.9
C4—C3—C2	112.70 (13)	C15—C16—H16	119.9
C1—C3—H3	109.5	C18—C17—C16	120.0 (2)
C4—C3—H3	109.5	C18—C17—H17	120.0
C2—C3—H3	109.5	C16—C17—H17	120.0
C5—C4—C3	112.65 (14)	C17—C18—C19	119.90 (19)
C5—C4—H4A	109.1	C17—C18—H18	120.1
C3—C4—H4A	109.1	C19—C18—H18	120.1
C5—C4—H4B	109.1	C18—C19—C14	120.98 (18)
C3—C4—H4B	109.1	C18—C19—H19	119.5
H4A—C4—H4B	107.8	C14—C19—H19	119.5
C6—C5—C4	126.20 (19)	N2—C20—C21	116.17 (14)
C6—C5—H5	116.9	N2—C20—H20A	108.2
C4—C5—H5	116.9	C21—C20—H20A	108.2
C5—C6—H6A	120.0	N2—C20—H20B	108.2
C5—C6—H6B	120.0	C21—C20—H20B	108.2
H6A—C6—H6B	120.0	H20A—C20—H20B	107.4
C12—C7—C8	119.37 (14)	C26—C21—C22	119.19 (18)
C12—C7—N1	119.39 (14)	C26—C21—C20	123.27 (15)
C8—C7—N1	121.20 (14)	C22—C21—C20	117.52 (18)
C9—C8—C7	119.02 (14)	C23—C22—C21	120.2 (2)
C9—C8—N2	119.64 (14)	C23—C22—H22	119.9
C7—C8—N2	121.34 (13)	C21—C22—H22	119.9
C10—C9—C8	120.93 (15)	C24—C23—C22	120.2 (2)
C10—C9—H9	119.5	C24—C23—H23	119.9
C8—C9—H9	119.5	C22—C23—H23	119.9
C9—C10—C11	119.97 (15)	C23—C24—C25	120.2 (2)
C9—C10—H10	120.0	C23—C24—H24	119.9
C11—C10—H10	120.0	C25—C24—H24	119.9
C12—C11—C10	119.91 (15)	C24—C25—C26	119.6 (3)
C12—C11—H11	120.0	C24—C25—H25	120.2
C10—C11—H11	120.0	C26—C25—H25	120.2
C11—C12—C7	120.77 (15)	C21—C26—C25	120.5 (2)
C11—C12—H12	119.6	C21—C26—H26	119.8
C7—C12—H12	119.6	C25—C26—H26	119.8

C7—N1—C1—O1	178.80 (15)	C7—C8—C9—C10	1.6 (2)
C13—N1—C1—O1	−0.6 (2)	N2—C8—C9—C10	−179.23 (15)
C7—N1—C1—C3	−5.8 (2)	C8—C9—C10—C11	−0.3 (2)
C13—N1—C1—C3	174.81 (13)	C9—C10—C11—C12	−1.1 (2)
C8—N2—C2—O2	177.22 (16)	C10—C11—C12—C7	1.2 (2)
C20—N2—C2—O2	0.8 (2)	C8—C7—C12—C11	0.1 (2)
C8—N2—C2—C3	1.5 (2)	N1—C7—C12—C11	−177.57 (14)
C20—N2—C2—C3	−174.87 (14)	C1—N1—C13—C14	−124.15 (16)
O1—C1—C3—C4	−19.6 (2)	C7—N1—C13—C14	56.45 (19)
N1—C1—C3—C4	164.96 (14)	N1—C13—C14—C15	34.5 (2)
O1—C1—C3—C2	101.85 (17)	N1—C13—C14—C19	−146.39 (15)
N1—C1—C3—C2	−73.59 (16)	C19—C14—C15—C16	0.8 (3)
O2—C2—C3—C1	−99.46 (19)	C13—C14—C15—C16	179.95 (18)
N2—C2—C3—C1	76.21 (17)	C14—C15—C16—C17	−0.8 (3)
O2—C2—C3—C4	22.0 (2)	C15—C16—C17—C18	−0.3 (3)
N2—C2—C3—C4	−162.32 (14)	C16—C17—C18—C19	1.4 (3)
C1—C3—C4—C5	−171.39 (14)	C17—C18—C19—C14	−1.3 (3)
C2—C3—C4—C5	73.10 (19)	C15—C14—C19—C18	0.2 (3)
C3—C4—C5—C6	140.7 (2)	C13—C14—C19—C18	−178.88 (17)
C1—N1—C7—C12	−129.21 (16)	C2—N2—C20—C21	−71.74 (19)
C13—N1—C7—C12	50.2 (2)	C8—N2—C20—C21	111.77 (17)
C1—N1—C7—C8	53.2 (2)	N2—C20—C21—C26	−9.8 (2)
C13—N1—C7—C8	−127.46 (16)	N2—C20—C21—C22	171.75 (15)
C12—C7—C8—C9	−1.5 (2)	C26—C21—C22—C23	−1.0 (3)
N1—C7—C8—C9	176.16 (14)	C20—C21—C22—C23	177.51 (17)
C12—C7—C8—N2	179.35 (14)	C21—C22—C23—C24	−0.1 (3)
N1—C7—C8—N2	−3.0 (2)	C22—C23—C24—C25	1.0 (4)
C2—N2—C8—C9	134.46 (16)	C23—C24—C25—C26	−0.8 (4)
C20—N2—C8—C9	−49.2 (2)	C22—C21—C26—C25	1.2 (3)
C2—N2—C8—C7	−46.4 (2)	C20—C21—C26—C25	−177.19 (17)
C20—N2—C8—C7	129.94 (16)	C24—C25—C26—C21	−0.4 (3)

Experimental details

Crystal data
Chemical formula	C₂₆H₂₄N₂O₂
M_r	396.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	193
a, b, c (Å)	9.2603 (4), 14.0037 (6), 16.2249 (7)
β (°)	91.996 (1)
V (Å³)	2102.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.40 × 0.07

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	27620, 4820, 2934
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.117, 1.00
No. of reflections	4820
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.18

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
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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