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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page o2805
https://doi.org/10.1107/S1600536810040134

3-(12-Bromo­dodec­yl)-1,5-di­methyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Rchida Dardouri,a Fouad Ouazzani Chahdi,a Natalie Saffon,b El Mokhtar Essassia and Seik Weng Ngc*

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, C23H35BrN2O2, 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 bromo­dodecyl substituent occupies an equatorial position, with the dodecyl 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[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.]). For the structure of a similar compound, 3-(6-bromo­hex­yl)-1,5-dimethyl-1,5-benzodiazepine-2,4-dione, see: Dardouri et al. (2010[Dardouri, R., Ouazzani Chahdi, F., Saffon, N., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o2804.]).

[Scheme 1]

Experimental

Crystal data

  • C23H35BrN2O2

  • Mr = 451.44

  • Monoclinic, P 21 /n

  • a = 7.5971 (1) Å

  • b = 10.5032 (2) Å

  • c = 28.7129 (5) Å

  • β = 95.213 (1)°

  • V = 2281.64 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.82 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.611, Tmax = 0.839

  • 24581 measured reflections

  • 6634 independent reflections

  • 4370 reflections with I > 2σ(I)

  • Rint = 0.037
Refinement

  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.099

  • S = 0.99

  • 6634 reflections

  • 255 parameters

  • H-atom parameters constrained

  • Δρmax = 0.61 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C2—H2⋯O1i 0.93 2.52 3.424 (2) 164
C7—H7B⋯O2ii 0.96 2.40 3.340 (2) 166
C11—H11C⋯O1ii 0.96 2.48 3.407 (2) 164
Symmetry codes: (i) [-x+{\script{1\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[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810040134/xu5050sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810040134/xu5050Isup2.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 1,12-dibromododecane 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). For the structure of a similar compound, 3-(6-bromohexyl)-1,5-dimethyl-1,5-benzodiazepine-2,4-dione, 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 1,12-dibromododecane (0.94 g, 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.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C).

Structure description 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 1,12-dibromododecane the title compound (Scheme I, Fig. 1).

For the crystal structure of 1,5-dimethyl-1,5-benzodiazepin-2,4-dione, see: Mondieig et al. (2005). For the structure of a similar compound, 3-(6-bromohexyl)-1,5-dimethyl-1,5-benzodiazepine-2,4-dione, see: Dardouri et al. (2010).

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
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C23H35BrN2O2 at the 50% probability level; hydrogen atoms are drawn as arbitrary radius.
3-(12-Bromododecyl)-1,5-dimethyl-1H-1,5-benzodiazepine- 2,4(3H,5H)-dione top
Crystal data top
C23H35BrN2O2F(000) = 952
Mr = 451.44Dx = 1.314 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5655 reflections
a = 7.5971 (1) Åθ = 2.4–25.4°
b = 10.5032 (2) ŵ = 1.82 mm−1
c = 28.7129 (5) ÅT = 293 K
β = 95.213 (1)°Prism, colorless
V = 2281.64 (7) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker X8 APEXII
diffractometer		6634 independent reflections
Radiation source: fine-focus sealed tube4370 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.037
φ and ω scansθmax = 30.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −10→10
Tmin = 0.611, Tmax = 0.839k = −14→12
24581 measured reflectionsl = −40→40
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0518P)2]
where P = (Fo2 + 2Fc2)/3
6634 reflections(Δ/σ)max = 0.001
255 parametersΔρmax = 0.61 e Å−3
0 restraintsΔρmin = −0.23 e Å−3
Crystal data top
C23H35BrN2O2V = 2281.64 (7) Å3
Mr = 451.44Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.5971 (1) ŵ = 1.82 mm−1
b = 10.5032 (2) ÅT = 293 K
c = 28.7129 (5) Å0.30 × 0.20 × 0.10 mm
β = 95.213 (1)°
Data collection top
Bruker X8 APEXII
diffractometer		6634 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4370 reflections with I > 2σ(I)
Tmin = 0.611, Tmax = 0.839Rint = 0.037
24581 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.099H-atom parameters constrained
S = 0.99Δρmax = 0.61 e Å−3
6634 reflectionsΔρmin = −0.23 e Å−3
255 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br11.65169 (3)1.558652 (19)0.586300 (7)0.04634 (9)
N10.0090 (2)0.57047 (12)0.26467 (5)0.0294 (3)
N2−0.32138 (19)0.57806 (12)0.30691 (5)0.0291 (3)
O10.08035 (17)0.77902 (11)0.26153 (4)0.0368 (3)
O2−0.35919 (17)0.78733 (11)0.32234 (5)0.0411 (3)
C1−0.0532 (2)0.46396 (15)0.28941 (6)0.0276 (4)
C20.0475 (2)0.35221 (16)0.29190 (7)0.0350 (4)
H20.15510.34970.27880.042*
C3−0.0126 (3)0.24597 (17)0.31369 (7)0.0411 (5)
H30.05490.17200.31540.049*
C4−0.1723 (3)0.24865 (17)0.33297 (7)0.0407 (5)
H4−0.21310.17620.34720.049*
C5−0.2713 (3)0.35867 (16)0.33120 (7)0.0347 (4)
H5−0.37810.36050.34470.042*
C6−0.2126 (2)0.46761 (15)0.30930 (6)0.0266 (4)
C70.0742 (3)0.54706 (17)0.21882 (6)0.0355 (4)
H7A0.06590.62400.20070.053*
H7B0.00410.48190.20270.053*
H7C0.19530.52000.22310.053*
C80.0180 (2)0.69084 (15)0.28235 (6)0.0285 (4)
C9−0.0598 (2)0.70942 (15)0.32913 (6)0.0273 (4)
H9−0.01650.64120.35050.033*
C10−0.2600 (2)0.69690 (16)0.31965 (6)0.0292 (4)
C11−0.5119 (2)0.56279 (17)0.29472 (7)0.0350 (4)
H11A−0.55920.63970.28050.053*
H11B−0.56900.54540.32250.053*
H11C−0.53200.49330.27320.053*
C12−0.0055 (2)0.83761 (16)0.35126 (7)0.0327 (4)
H12A−0.02000.90370.32760.039*
H12B−0.08230.85760.37550.039*
C130.1849 (2)0.83595 (15)0.37232 (6)0.0329 (4)
H13A0.25970.80920.34850.039*
H13B0.19650.77320.39720.039*
C140.2511 (2)0.96386 (16)0.39196 (7)0.0328 (4)
H14A0.24371.02620.36690.039*
H14B0.17450.99210.41520.039*
C150.4398 (3)0.95858 (15)0.41418 (7)0.0335 (4)
H15A0.51420.92290.39180.040*
H15B0.44460.90150.44080.040*
C160.5151 (3)1.08722 (16)0.43040 (7)0.0348 (4)
H16A0.51331.14390.40370.042*
H16B0.43981.12390.45240.042*
C170.7028 (3)1.07876 (15)0.45343 (7)0.0354 (4)
H17A0.77791.04310.43120.043*
H17B0.70451.02060.47970.043*
C180.7796 (3)1.20563 (16)0.47064 (7)0.0365 (4)
H18A0.78191.26290.44420.044*
H18B0.70251.24270.49210.044*
C190.9648 (3)1.19565 (16)0.49503 (7)0.0383 (4)
H19A1.04181.15930.47340.046*
H19B0.96251.13730.52120.046*
C201.0436 (3)1.32136 (16)0.51308 (7)0.0362 (4)
H20A1.04391.38080.48720.043*
H20B0.96961.35680.53570.043*
C211.2304 (3)1.30689 (16)0.53584 (7)0.0370 (4)
H21A1.30131.26510.51390.044*
H21B1.22781.25160.56280.044*
C221.3211 (3)1.43160 (15)0.55161 (7)0.0365 (4)
H22A1.32161.48940.52530.044*
H22B1.25691.47180.57530.044*
C231.5070 (3)1.40468 (18)0.57104 (7)0.0409 (5)
H23A1.56431.35420.54850.049*
H23B1.50381.35390.59920.049*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.05160 (15)0.04100 (12)0.04792 (14)−0.01138 (9)0.01260 (10)−0.00678 (9)
N10.0297 (8)0.0275 (7)0.0323 (8)−0.0030 (6)0.0092 (6)−0.0026 (6)
N20.0229 (7)0.0252 (7)0.0392 (8)0.0003 (5)0.0030 (6)−0.0004 (6)
O10.0387 (7)0.0305 (6)0.0421 (7)−0.0073 (5)0.0089 (6)0.0033 (5)
O20.0327 (7)0.0307 (7)0.0598 (9)0.0082 (6)0.0037 (6)−0.0064 (6)
C10.0281 (9)0.0249 (8)0.0300 (9)−0.0010 (7)0.0030 (7)−0.0014 (6)
C20.0304 (10)0.0325 (9)0.0428 (11)0.0046 (7)0.0072 (8)−0.0037 (8)
C30.0466 (12)0.0276 (9)0.0492 (12)0.0100 (8)0.0057 (9)0.0017 (8)
C40.0507 (12)0.0294 (9)0.0433 (11)−0.0005 (8)0.0114 (9)0.0078 (8)
C50.0340 (10)0.0311 (9)0.0405 (10)−0.0021 (7)0.0116 (8)0.0013 (7)
C60.0257 (9)0.0238 (8)0.0305 (9)0.0006 (6)0.0029 (7)−0.0015 (6)
C70.0343 (10)0.0403 (10)0.0331 (10)−0.0048 (8)0.0097 (8)−0.0036 (8)
C80.0230 (9)0.0274 (8)0.0348 (9)−0.0007 (7)0.0002 (7)−0.0007 (7)
C90.0255 (9)0.0239 (8)0.0323 (9)0.0008 (6)0.0015 (7)−0.0024 (6)
C100.0286 (9)0.0275 (8)0.0317 (9)0.0023 (7)0.0041 (7)−0.0009 (7)
C110.0254 (9)0.0361 (9)0.0431 (11)−0.0003 (8)0.0002 (8)−0.0007 (8)
C120.0322 (10)0.0257 (8)0.0402 (10)0.0003 (7)0.0031 (8)−0.0054 (7)
C130.0360 (10)0.0253 (8)0.0371 (10)−0.0006 (7)0.0017 (8)−0.0047 (7)
C140.0375 (10)0.0258 (8)0.0351 (10)−0.0005 (7)0.0034 (8)−0.0030 (7)
C150.0396 (11)0.0257 (9)0.0345 (10)−0.0019 (7)0.0000 (8)−0.0036 (7)
C160.0414 (11)0.0252 (9)0.0378 (10)−0.0010 (7)0.0038 (8)−0.0046 (7)
C170.0426 (11)0.0263 (9)0.0366 (10)−0.0045 (7)−0.0009 (8)−0.0050 (7)
C180.0429 (11)0.0252 (9)0.0412 (10)−0.0027 (8)0.0024 (9)−0.0049 (7)
C190.0449 (11)0.0287 (9)0.0400 (11)−0.0014 (8)−0.0025 (9)−0.0040 (8)
C200.0419 (11)0.0281 (9)0.0384 (10)−0.0033 (8)0.0028 (8)−0.0039 (7)
C210.0454 (11)0.0271 (9)0.0377 (10)−0.0014 (8)−0.0006 (9)−0.0021 (7)
C220.0435 (11)0.0272 (9)0.0384 (10)−0.0023 (8)0.0023 (9)−0.0027 (7)
C230.0442 (12)0.0322 (9)0.0457 (11)−0.0041 (8)0.0003 (9)−0.0067 (8)
Geometric parameters (Å, º) top
Br1—C231.9818 (19)C13—C141.525 (2)
N1—C81.362 (2)C13—H13A0.9700
N1—C11.428 (2)C13—H13B0.9700
N1—C71.469 (2)C14—C151.516 (3)
N2—C101.371 (2)C14—H14A0.9700
N2—C61.423 (2)C14—H14B0.9700
N2—C111.466 (2)C15—C161.523 (2)
O1—C81.221 (2)C15—H15A0.9700
O2—C101.219 (2)C15—H15B0.9700
C1—C61.386 (2)C16—C171.519 (3)
C1—C21.399 (2)C16—H16A0.9700
C2—C31.377 (3)C16—H16B0.9700
C2—H20.9300C17—C181.519 (2)
C3—C41.378 (3)C17—H17A0.9700
C3—H30.9300C17—H17B0.9700
C4—C51.377 (3)C18—C191.517 (3)
C4—H40.9300C18—H18A0.9700
C5—C61.398 (2)C18—H18B0.9700
C5—H50.9300C19—C201.521 (2)
C7—H7A0.9600C19—H19A0.9700
C7—H7B0.9600C19—H19B0.9700
C7—H7C0.9600C20—C211.515 (3)
C8—C91.528 (2)C20—H20A0.9700
C9—C101.526 (2)C20—H20B0.9700
C9—C121.529 (2)C21—C221.529 (2)
C9—H90.9800C21—H21A0.9700
C11—H11A0.9600C21—H21B0.9700
C11—H11B0.9600C22—C231.497 (3)
C11—H11C0.9600C22—H22A0.9700
C12—C131.516 (3)C22—H22B0.9700
C12—H12A0.9700C23—H23A0.9700
C12—H12B0.9700C23—H23B0.9700
C8—N1—C1123.32 (14)C15—C14—C13113.01 (14)
C8—N1—C7118.69 (14)C15—C14—H14A109.0
C1—N1—C7117.93 (13)C13—C14—H14A109.0
C10—N2—C6123.20 (14)C15—C14—H14B109.0
C10—N2—C11117.90 (14)C13—C14—H14B109.0
C6—N2—C11118.61 (13)H14A—C14—H14B107.8
C6—C1—C2119.76 (15)C14—C15—C16114.23 (14)
C6—C1—N1121.61 (15)C14—C15—H15A108.7
C2—C1—N1118.59 (15)C16—C15—H15A108.7
C3—C2—C1120.02 (17)C14—C15—H15B108.7
C3—C2—H2120.0C16—C15—H15B108.7
C1—C2—H2120.0H15A—C15—H15B107.6
C2—C3—C4120.41 (17)C17—C16—C15113.12 (14)
C2—C3—H3119.8C17—C16—H16A109.0
C4—C3—H3119.8C15—C16—H16A109.0
C5—C4—C3120.00 (17)C17—C16—H16B109.0
C5—C4—H4120.0C15—C16—H16B109.0
C3—C4—H4120.0H16A—C16—H16B107.8
C4—C5—C6120.50 (17)C16—C17—C18114.08 (14)
C4—C5—H5119.7C16—C17—H17A108.7
C6—C5—H5119.7C18—C17—H17A108.7
C1—C6—C5119.30 (15)C16—C17—H17B108.7
C1—C6—N2121.91 (14)C18—C17—H17B108.7
C5—C6—N2118.76 (15)H17A—C17—H17B107.6
N1—C7—H7A109.5C19—C18—C17113.72 (15)
N1—C7—H7B109.5C19—C18—H18A108.8
H7A—C7—H7B109.5C17—C18—H18A108.8
N1—C7—H7C109.5C19—C18—H18B108.8
H7A—C7—H7C109.5C17—C18—H18B108.8
H7B—C7—H7C109.5H18A—C18—H18B107.7
O1—C8—N1122.01 (16)C18—C19—C20114.64 (15)
O1—C8—C9122.12 (15)C18—C19—H19A108.6
N1—C8—C9115.85 (14)C20—C19—H19A108.6
C10—C9—C8106.92 (14)C18—C19—H19B108.6
C10—C9—C12112.15 (14)C20—C19—H19B108.6
C8—C9—C12111.47 (14)H19A—C19—H19B107.6
C10—C9—H9108.7C21—C20—C19112.58 (15)
C8—C9—H9108.7C21—C20—H20A109.1
C12—C9—H9108.7C19—C20—H20A109.1
O2—C10—N2121.92 (16)C21—C20—H20B109.1
O2—C10—C9122.23 (15)C19—C20—H20B109.1
N2—C10—C9115.83 (14)H20A—C20—H20B107.8
N2—C11—H11A109.5C20—C21—C22114.90 (15)
N2—C11—H11B109.5C20—C21—H21A108.5
H11A—C11—H11B109.5C22—C21—H21A108.5
N2—C11—H11C109.5C20—C21—H21B108.5
H11A—C11—H11C109.5C22—C21—H21B108.5
H11B—C11—H11C109.5H21A—C21—H21B107.5
C13—C12—C9111.55 (14)C23—C22—C21109.44 (14)
C13—C12—H12A109.3C23—C22—H22A109.8
C9—C12—H12A109.3C21—C22—H22A109.8
C13—C12—H12B109.3C23—C22—H22B109.8
C9—C12—H12B109.3C21—C22—H22B109.8
H12A—C12—H12B108.0H22A—C22—H22B108.2
C12—C13—C14114.09 (14)C22—C23—Br1114.43 (12)
C12—C13—H13A108.7C22—C23—H23A108.7
C14—C13—H13A108.7Br1—C23—H23A108.7
C12—C13—H13B108.7C22—C23—H23B108.7
C14—C13—H13B108.7Br1—C23—H23B108.7
H13A—C13—H13B107.6H23A—C23—H23B107.6
C8—N1—C1—C650.6 (2)N1—C8—C9—C10−70.41 (18)
C7—N1—C1—C6−132.37 (17)O1—C8—C9—C12−15.1 (2)
C8—N1—C1—C2−131.72 (18)N1—C8—C9—C12166.69 (15)
C7—N1—C1—C245.3 (2)C6—N2—C10—O2−171.56 (16)
C6—C1—C2—C30.6 (3)C11—N2—C10—O22.2 (3)
N1—C1—C2—C3−177.09 (17)C6—N2—C10—C99.8 (2)
C1—C2—C3—C40.3 (3)C11—N2—C10—C9−176.45 (15)
C2—C3—C4—C5−1.1 (3)C8—C9—C10—O2−111.04 (18)
C3—C4—C5—C61.0 (3)C12—C9—C10—O211.4 (2)
C2—C1—C6—C5−0.7 (3)C8—C9—C10—N267.61 (18)
N1—C1—C6—C5176.96 (16)C12—C9—C10—N2−169.93 (15)
C2—C1—C6—N2−178.75 (16)C10—C9—C12—C13164.64 (15)
N1—C1—C6—N2−1.1 (3)C8—C9—C12—C13−75.51 (19)
C4—C5—C6—C1−0.1 (3)C9—C12—C13—C14175.98 (15)
C4—C5—C6—N2178.02 (17)C12—C13—C14—C15178.16 (16)
C10—N2—C6—C1−51.4 (2)C13—C14—C15—C16175.04 (15)
C11—N2—C6—C1134.90 (17)C14—C15—C16—C17178.80 (16)
C10—N2—C6—C5130.52 (18)C15—C16—C17—C18−179.03 (16)
C11—N2—C6—C5−43.2 (2)C16—C17—C18—C19178.06 (17)
C1—N1—C8—O1176.05 (16)C17—C18—C19—C20−179.30 (17)
C7—N1—C8—O1−0.9 (3)C18—C19—C20—C21−178.30 (16)
C1—N1—C8—C9−5.7 (2)C19—C20—C21—C22175.93 (17)
C7—N1—C8—C9177.33 (15)C20—C21—C22—C23−177.00 (16)
O1—C8—C9—C10107.82 (18)C21—C22—C23—Br1173.24 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O1i0.932.523.424 (2)164
C7—H7B···O2ii0.962.403.340 (2)166
C11—H11C···O1ii0.962.483.407 (2)164
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x−1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC23H35BrN2O2
Mr451.44
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)7.5971 (1), 10.5032 (2), 28.7129 (5)
β (°) 95.213 (1)
V (Å3)2281.64 (7)
Z4
Radiation typeMo Kα
µ (mm−1)1.82
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerBruker X8 APEXII
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.611, 0.839
No. of measured, independent and
observed [I > 2σ(I)] reflections		24581, 6634, 4370
Rint0.037
(sin θ/λ)max (Å−1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.099, 0.99
No. of reflections6634
No. of parameters255
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.61, −0.23

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···AD—HH···AD···AD—H···A
C2—H2···O1i0.932.523.424 (2)164
C7—H7B···O2ii0.962.403.340 (2)166
C11—H11C···O1ii0.962.483.407 (2)164
Symmetry codes: (i) −x+1/2, 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

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
 First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationDardouri, R., Ouazzani Chahdi, F., Saffon, N., Essassi, E. M. & Ng, S. W. (2010). Acta Cryst. E66, o2804.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationMondieig, 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
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 66| Part 11| November 2010| Page o2805
https://doi.org/10.1107/S1600536810040134
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