3-(6-Bromo­hex­yl)-1,5-dimethyl-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/S1600536810040122

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2804

https://doi.org/10.1107/S1600536810040122

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3-(6-Bromohexyl)-1,5-dimethyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Rchida 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, BP 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 6 October 2010; accepted 7 October 2010; online 13 October 2010)

The seven-membered ring in the title compound, C₁₇H₂₃BrN₂O₂, 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 bromohexyl substituent occupies an equatorial position, with the hexyl chain exhibiting an extended conformation. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the crystal structure of 1,5-dimethyl-1,5-benzodiazepin-2,4-dione, see: Mondieig et al. (2005 ).

Experimental

Crystal data

C₁₇H₂₃BrN₂O₂
M_r = 367.28
Monoclinic, P 2₁ /n
a = 7.5214 (1) Å
b = 9.3693 (2) Å
c = 23.8686 (5) Å
β = 91.750 (1)°
V = 1681.24 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.45 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker X8 APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.526, T_max = 0.791
25590 measured reflections
4897 independent reflections
3478 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.153
S = 1.01
4897 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 1.92 e Å⁻³
Δρ_min = −0.68 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯O1ⁱ	0.96	2.58	3.430 (3)	147
C7—H7C⋯O2ⁱⁱ	0.96	2.51	3.471 (3)	174
C11—H11B⋯O1ⁱⁱ	0.96	2.60	3.551 (3)	173
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: https://doi.org/10.1107/S1600536810040122/xu5049sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810040122/xu5049Isup2.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 this study, the compound is reacted with 1,6-dibromohexane the title compound (Scheme I, Fig. 1).

Related literature top

For the crystal structure of 1,5-dimethyl-1,5-benzodiazepin-2,4-dione, see: Mondieig et al. (2005).

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 1,6-dibromodohexane (0.40 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.

Structure description top

For the crystal structure of 1,5-dimethyl-1,5-benzodiazepin-2,4-dione, see: Mondieig et al. (2005).

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 C₁₇H₂₃BrN₂O₂ at the 50% probability level; hydrogen atoms are drawn as arbitrary radius.

3-(6-Bromohexyl)-1,5-dimethyl-1H-1,5-benzodiazepine- 2,4(3H,5H)-dione top

Crystal data top

C₁₇H₂₃BrN₂O₂	F(000) = 760
M_r = 367.28	D_x = 1.451 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5411 reflections
a = 7.5214 (1) Å	θ = 2.3–26.0°
b = 9.3693 (2) Å	µ = 2.45 mm⁻¹
c = 23.8686 (5) Å	T = 293 K
β = 91.750 (1)°	Prism, colorless
V = 1681.24 (6) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker X8 APEXII diffractometer	4897 independent reflections
Radiation source: fine-focus sealed tube	3478 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
φ and ω scans	θ_max = 30.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
T_min = 0.526, T_max = 0.791	k = −13→13
25590 measured reflections	l = −28→33

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.082P)² + 1.8005P] where P = (F_o² + 2F_c²)/3
4897 reflections	(Δ/σ)_max = 0.001
201 parameters	Δρ_max = 1.92 e Å⁻³
0 restraints	Δρ_min = −0.68 e Å⁻³

Crystal data top

C₁₇H₂₃BrN₂O₂	V = 1681.24 (6) Å³
M_r = 367.28	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.5214 (1) Å	µ = 2.45 mm⁻¹
b = 9.3693 (2) Å	T = 293 K
c = 23.8686 (5) Å	0.30 × 0.20 × 0.10 mm
β = 91.750 (1)°

Data collection top

Bruker X8 APEXII diffractometer	4897 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3478 reflections with I > 2σ(I)
T_min = 0.526, T_max = 0.791	R_int = 0.045
25590 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.153	H-atom parameters constrained
S = 1.01	Δρ_max = 1.92 e Å⁻³
4897 reflections	Δρ_min = −0.68 e Å⁻³
201 parameters

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

	x	y	z	U_iso*/U_eq
Br1	1.30982 (5)	0.07856 (4)	0.564211 (15)	0.04567 (14)
O1	0.5859 (3)	0.4826 (2)	0.28329 (9)	0.0297 (4)
O2	0.1496 (3)	0.4797 (2)	0.35848 (10)	0.0351 (5)
N1	0.5074 (3)	0.7166 (2)	0.27741 (9)	0.0211 (4)
N2	0.1710 (3)	0.7124 (2)	0.33415 (9)	0.0231 (4)
C1	0.4344 (3)	0.8410 (3)	0.30158 (10)	0.0199 (5)
C2	0.5247 (4)	0.9710 (3)	0.29605 (11)	0.0247 (5)
H2	0.6331	0.9729	0.2783	0.030*
C3	0.4550 (4)	1.0961 (3)	0.31659 (12)	0.0278 (6)
H3	0.5153	1.1818	0.3119	0.033*
C4	0.2944 (4)	1.0944 (3)	0.34434 (12)	0.0266 (5)
H4	0.2476	1.1784	0.3585	0.032*
C5	0.2056 (4)	0.9665 (3)	0.35053 (11)	0.0251 (5)
H5	0.0991	0.9651	0.3693	0.030*
C6	0.2725 (3)	0.8394 (3)	0.32918 (10)	0.0203 (5)
C7	0.5848 (3)	0.7301 (3)	0.22189 (11)	0.0244 (5)
H7A	0.5875	0.6381	0.2042	0.037*
H7B	0.7036	0.7667	0.2259	0.037*
H7C	0.5137	0.7942	0.1992	0.037*
C8	0.5209 (3)	0.5879 (3)	0.30474 (11)	0.0215 (5)
C9	0.4425 (4)	0.5856 (3)	0.36297 (11)	0.0233 (5)
H9	0.4770	0.6735	0.3827	0.028*
C10	0.2407 (4)	0.5863 (3)	0.35245 (11)	0.0237 (5)
C11	−0.0223 (3)	0.7209 (3)	0.32308 (12)	0.0281 (6)
H11A	−0.0647	0.6313	0.3084	0.042*
H11B	−0.0476	0.7951	0.2962	0.042*
H11C	−0.0807	0.7419	0.3573	0.042*
C12	0.5012 (4)	0.4579 (3)	0.39872 (12)	0.0291 (6)
H12A	0.4395	0.4608	0.4338	0.035*
H12B	0.4662	0.3709	0.3794	0.035*
C13	0.6995 (4)	0.4532 (3)	0.41145 (14)	0.0363 (7)
H13A	0.7388	0.5469	0.4239	0.044*
H13B	0.7603	0.4312	0.3772	0.044*
C14	0.7533 (4)	0.3430 (3)	0.45629 (14)	0.0372 (7)
H14A	0.7202	0.3782	0.4927	0.045*
H14B	0.6884	0.2551	0.4491	0.045*
C15	0.9504 (5)	0.3118 (4)	0.45750 (15)	0.0462 (8)
H15A	1.0143	0.4018	0.4588	0.055*
H15B	0.9794	0.2646	0.4228	0.055*
C16	1.0164 (4)	0.2199 (3)	0.50614 (13)	0.0360 (7)
H16A	1.0014	0.2709	0.5411	0.043*
H16B	0.9465	0.1331	0.5074	0.043*
C17	1.2095 (5)	0.1827 (5)	0.50011 (14)	0.0469 (8)
H17A	1.2768	0.2699	0.4953	0.056*
H17B	1.2219	0.1253	0.4666	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0511 (2)	0.0394 (2)	0.0454 (2)	0.00836 (15)	−0.01604 (15)	−0.00333 (14)
O1	0.0329 (10)	0.0220 (9)	0.0342 (10)	0.0060 (8)	0.0014 (8)	−0.0021 (8)
O2	0.0311 (11)	0.0260 (10)	0.0482 (13)	−0.0106 (8)	0.0014 (9)	0.0044 (9)
N1	0.0222 (10)	0.0170 (9)	0.0243 (10)	0.0011 (8)	0.0034 (8)	−0.0001 (8)
N2	0.0189 (10)	0.0223 (10)	0.0283 (11)	−0.0039 (8)	0.0017 (8)	0.0011 (8)
C1	0.0204 (11)	0.0177 (11)	0.0215 (11)	0.0023 (9)	−0.0003 (9)	0.0006 (9)
C2	0.0231 (12)	0.0213 (11)	0.0299 (13)	−0.0023 (10)	0.0051 (10)	0.0017 (10)
C3	0.0310 (14)	0.0196 (12)	0.0329 (14)	−0.0041 (10)	0.0022 (11)	0.0000 (10)
C4	0.0279 (13)	0.0209 (12)	0.0309 (13)	0.0027 (10)	−0.0004 (10)	−0.0027 (10)
C5	0.0220 (12)	0.0259 (12)	0.0276 (13)	0.0017 (10)	0.0024 (10)	−0.0006 (10)
C6	0.0187 (11)	0.0195 (11)	0.0227 (11)	−0.0019 (9)	−0.0011 (9)	0.0008 (9)
C7	0.0242 (12)	0.0257 (12)	0.0234 (12)	0.0011 (10)	0.0033 (9)	−0.0011 (10)
C8	0.0193 (11)	0.0171 (11)	0.0281 (12)	−0.0003 (9)	−0.0020 (9)	−0.0003 (9)
C9	0.0266 (12)	0.0166 (11)	0.0264 (12)	−0.0020 (9)	−0.0009 (10)	0.0013 (9)
C10	0.0258 (12)	0.0218 (12)	0.0237 (12)	−0.0042 (10)	0.0029 (9)	−0.0007 (9)
C11	0.0183 (11)	0.0328 (14)	0.0330 (14)	−0.0036 (10)	−0.0004 (10)	−0.0013 (11)
C12	0.0359 (15)	0.0201 (11)	0.0311 (14)	−0.0012 (11)	−0.0019 (11)	0.0030 (10)
C13	0.0343 (15)	0.0339 (15)	0.0403 (16)	−0.0016 (13)	−0.0050 (12)	0.0139 (13)
C14	0.0436 (17)	0.0312 (15)	0.0365 (16)	0.0045 (13)	−0.0029 (13)	0.0103 (12)
C15	0.0474 (19)	0.054 (2)	0.0369 (17)	0.0059 (17)	−0.0025 (14)	0.0178 (15)
C16	0.0428 (17)	0.0348 (15)	0.0298 (14)	−0.0013 (13)	−0.0064 (12)	0.0079 (12)
C17	0.0480 (19)	0.059 (2)	0.0334 (16)	0.0098 (17)	−0.0005 (14)	0.0101 (15)

Geometric parameters (Å, º) top

Br1—C17	1.947 (3)	C9—C12	1.527 (4)
O1—C8	1.221 (3)	C9—C10	1.531 (4)
O2—C10	1.222 (3)	C9—H9	0.9800
N1—C8	1.373 (3)	C11—H11A	0.9600
N1—C1	1.419 (3)	C11—H11B	0.9600
N1—C7	1.469 (3)	C11—H11C	0.9600
N2—C10	1.359 (3)	C12—C13	1.514 (4)
N2—C6	1.420 (3)	C12—H12A	0.9700
N2—C11	1.472 (3)	C12—H12B	0.9700
C1—C6	1.402 (3)	C13—C14	1.533 (4)
C1—C2	1.402 (4)	C13—H13A	0.9700
C2—C3	1.380 (4)	C13—H13B	0.9700
C2—H2	0.9300	C14—C15	1.511 (5)
C3—C4	1.396 (4)	C14—H14A	0.9700
C3—H3	0.9300	C14—H14B	0.9700
C4—C5	1.382 (4)	C15—C16	1.517 (4)
C4—H4	0.9300	C15—H15A	0.9700
C5—C6	1.395 (4)	C15—H15B	0.9700
C5—H5	0.9300	C16—C17	1.505 (5)
C7—H7A	0.9600	C16—H16A	0.9700
C7—H7B	0.9600	C16—H16B	0.9700
C7—H7C	0.9600	C17—H17A	0.9700
C8—C9	1.526 (4)	C17—H17B	0.9700

C8—N1—C1	123.5 (2)	N2—C11—H11A	109.5
C8—N1—C7	118.6 (2)	N2—C11—H11B	109.5
C1—N1—C7	117.7 (2)	H11A—C11—H11B	109.5
C10—N2—C6	123.5 (2)	N2—C11—H11C	109.5
C10—N2—C11	118.3 (2)	H11A—C11—H11C	109.5
C6—N2—C11	118.0 (2)	H11B—C11—H11C	109.5
C6—C1—C2	118.9 (2)	C13—C12—C9	113.7 (2)
C6—C1—N1	122.3 (2)	C13—C12—H12A	108.8
C2—C1—N1	118.7 (2)	C9—C12—H12A	108.8
C3—C2—C1	120.9 (2)	C13—C12—H12B	108.8
C3—C2—H2	119.5	C9—C12—H12B	108.8
C1—C2—H2	119.5	H12A—C12—H12B	107.7
C2—C3—C4	120.2 (2)	C12—C13—C14	113.4 (3)
C2—C3—H3	119.9	C12—C13—H13A	108.9
C4—C3—H3	119.9	C14—C13—H13A	108.9
C5—C4—C3	119.3 (2)	C12—C13—H13B	108.9
C5—C4—H4	120.4	C14—C13—H13B	108.9
C3—C4—H4	120.4	H13A—C13—H13B	107.7
C4—C5—C6	121.4 (2)	C15—C14—C13	112.4 (3)
C4—C5—H5	119.3	C15—C14—H14A	109.1
C6—C5—H5	119.3	C13—C14—H14A	109.1
C5—C6—C1	119.4 (2)	C15—C14—H14B	109.1
C5—C6—N2	118.9 (2)	C13—C14—H14B	109.1
C1—C6—N2	121.7 (2)	H14A—C14—H14B	107.9
N1—C7—H7A	109.5	C14—C15—C16	115.0 (3)
N1—C7—H7B	109.5	C14—C15—H15A	108.5
H7A—C7—H7B	109.5	C16—C15—H15A	108.5
N1—C7—H7C	109.5	C14—C15—H15B	108.5
H7A—C7—H7C	109.5	C16—C15—H15B	108.5
H7B—C7—H7C	109.5	H15A—C15—H15B	107.5
O1—C8—N1	122.4 (2)	C17—C16—C15	110.6 (3)
O1—C8—C9	122.8 (2)	C17—C16—H16A	109.5
N1—C8—C9	114.8 (2)	C15—C16—H16A	109.5
C12—C9—C8	114.0 (2)	C17—C16—H16B	109.5
C12—C9—C10	111.3 (2)	C15—C16—H16B	109.5
C8—C9—C10	105.0 (2)	H16A—C16—H16B	108.1
C12—C9—H9	108.8	C16—C17—Br1	113.1 (2)
C8—C9—H9	108.8	C16—C17—H17A	109.0
C10—C9—H9	108.8	Br1—C17—H17A	109.0
O2—C10—N2	122.4 (3)	C16—C17—H17B	109.0
O2—C10—C9	122.3 (2)	Br1—C17—H17B	109.0
N2—C10—C9	115.3 (2)	H17A—C17—H17B	107.8

C8—N1—C1—C6	−47.6 (3)	C1—N1—C8—C9	2.9 (3)
C7—N1—C1—C6	137.3 (2)	C7—N1—C8—C9	177.9 (2)
C8—N1—C1—C2	134.5 (3)	O1—C8—C9—C12	17.7 (4)
C7—N1—C1—C2	−40.6 (3)	N1—C8—C9—C12	−164.4 (2)
C6—C1—C2—C3	−1.0 (4)	O1—C8—C9—C10	−104.4 (3)
N1—C1—C2—C3	177.0 (2)	N1—C8—C9—C10	73.5 (3)
C1—C2—C3—C4	1.3 (4)	C6—N2—C10—O2	177.1 (3)
C2—C3—C4—C5	−0.6 (4)	C11—N2—C10—O2	2.0 (4)
C3—C4—C5—C6	−0.6 (4)	C6—N2—C10—C9	−5.0 (4)
C4—C5—C6—C1	0.9 (4)	C11—N2—C10—C9	179.9 (2)
C4—C5—C6—N2	−176.7 (2)	C12—C9—C10—O2	−18.6 (4)
C2—C1—C6—C5	−0.2 (4)	C8—C9—C10—O2	105.2 (3)
N1—C1—C6—C5	−178.1 (2)	C12—C9—C10—N2	163.5 (2)
C2—C1—C6—N2	177.4 (2)	C8—C9—C10—N2	−72.7 (3)
N1—C1—C6—N2	−0.5 (4)	C8—C9—C12—C13	62.5 (3)
C10—N2—C6—C5	−133.0 (3)	C10—C9—C12—C13	−178.9 (2)
C11—N2—C6—C5	42.1 (3)	C9—C12—C13—C14	168.8 (3)
C10—N2—C6—C1	49.5 (4)	C12—C13—C14—C15	164.8 (3)
C11—N2—C6—C1	−135.5 (3)	C13—C14—C15—C16	171.7 (3)
C1—N1—C8—O1	−179.2 (2)	C14—C15—C16—C17	174.1 (3)
C7—N1—C8—O1	−4.1 (4)	C15—C16—C17—Br1	175.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O1ⁱ	0.96	2.58	3.430 (3)	147
C7—H7C···O2ⁱⁱ	0.96	2.51	3.471 (3)	174
C11—H11B···O1ⁱⁱ	0.96	2.60	3.551 (3)	173

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₃BrN₂O₂
M_r	367.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	7.5214 (1), 9.3693 (2), 23.8686 (5)
β (°)	91.750 (1)
V (Å³)	1681.24 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.45
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker X8 APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.526, 0.791
No. of measured, independent and observed [I > 2σ(I)] reflections	25590, 4897, 3478
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.153, 1.01
No. of reflections	4897
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.92, −0.68

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
C7—H7B···O1ⁱ	0.96	2.58	3.430 (3)	147
C7—H7C···O2ⁱⁱ	0.96	2.51	3.471 (3)	174
C11—H11B···O1ⁱⁱ	0.96	2.60	3.551 (3)	173

Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2.

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
Mondieig, M., Négrier, Ph., Léger, J. M., Benali, B., Lazar, Z., Elassyry, A., Jarmouni, C., Lakhrissi, B. & Massoui, M. (2005). Anal. Sci. X-Ray Struct. Anal. Online, 21, x145–x146. CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. 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