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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 5| May 2011| Page o1155

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

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[Dardouri, R., Ouazzani Chahdi, F., Saffon, N., Essassi, E. M. & Ng, S. W. (2011). Acta Cryst. E67, o674.]).

[Scheme 1]

Experimental

Crystal data
  • C27H44N2O2

  • Mr = 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)

  • Rint = 0.036

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 0.159

  • S = 1.03

  • 7353 reflections

  • 282 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.26 e Å−3

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


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.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93–0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C). Two reflections with bad agreements (0 2 0, 0 4 0) were omitted from the refinemnt.

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 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
C27H44N2O2F(000) = 944
Mr = 428.64Dx = 1.127 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9990 reflections
a = 8.1426 (1) Åθ = 2.6–30.0°
b = 36.2705 (5) ŵ = 0.07 mm1
c = 9.4090 (1) ÅT = 293 K
β = 114.611 (1)°Plate, colorless
V = 2526.38 (5) Å30.50 × 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 tubeRint = 0.036
Graphite monochromatorθmax = 30.0°, θmin = 2.5°
ϕ and ω scansh = 1011
45223 measured reflectionsk = 5051
7353 independent reflectionsl = 1213
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0871P)2 + 0.3018P]
where P = (Fo2 + 2Fc2)/3
7353 reflections(Δ/σ)max = 0.001
282 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C27H44N2O2V = 2526.38 (5) Å3
Mr = 428.64Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.1426 (1) ŵ = 0.07 mm1
b = 36.2705 (5) ÅT = 293 K
c = 9.4090 (1) Å0.50 × 0.30 × 0.10 mm
β = 114.611 (1)°
Data collection top
Bruker X8 APEXII
diffractometer
5105 reflections with I > 2σ(I)
45223 measured reflectionsRint = 0.036
7353 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.159H-atom parameters constrained
S = 1.03Δρmax = 0.34 e Å3
7353 reflectionsΔρmin = 0.26 e Å3
282 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.02825 (12)0.20901 (2)0.37201 (10)0.0323 (2)
O20.39162 (13)0.17141 (3)0.40983 (10)0.0376 (2)
N10.19184 (13)0.22225 (3)0.13447 (11)0.0271 (2)
N20.51023 (13)0.19449 (3)0.16414 (12)0.0268 (2)
C10.35060 (17)0.21187 (3)0.00186 (14)0.0273 (3)
C20.3522 (2)0.21567 (4)0.14654 (15)0.0400 (3)
H20.24980.22430.15600.048*
C30.5039 (2)0.20671 (4)0.27923 (16)0.0491 (4)
H30.50280.20880.37730.059*
C40.6573 (2)0.19462 (4)0.26542 (17)0.0485 (4)
H40.76060.18910.35460.058*
C50.65797 (19)0.19072 (3)0.11957 (16)0.0384 (3)
H50.76210.18250.11170.046*
C60.50464 (16)0.19891 (3)0.01618 (14)0.0267 (3)
C70.67424 (18)0.20524 (4)0.18255 (19)0.0388 (3)
H7A0.64150.21510.28550.058*
H7B0.75010.18400.16810.058*
H7C0.73830.22360.10610.058*
C80.37885 (16)0.17653 (3)0.28661 (13)0.0249 (2)
C90.21270 (15)0.16463 (3)0.26138 (13)0.0233 (2)
H9A0.25220.15290.15870.028*
C100.11159 (16)0.20013 (3)0.26219 (13)0.0237 (2)
C110.09947 (19)0.25653 (4)0.12803 (18)0.0384 (3)
H11A0.01950.26380.23210.058*
H11B0.18730.27560.08060.058*
H11C0.03120.25260.06720.058*
C120.09467 (16)0.13780 (3)0.38687 (13)0.0268 (3)
H12A0.16900.11760.39400.032*
H12B0.04520.15040.48700.032*
C130.06032 (17)0.12220 (3)0.35425 (14)0.0304 (3)
H13A0.01080.10730.26010.036*
H13B0.12660.14240.33540.036*
C140.19019 (17)0.09876 (3)0.48780 (14)0.0279 (3)
H14A0.12430.07820.50460.034*
H14B0.23670.11340.58260.034*
C150.34868 (17)0.08387 (3)0.45879 (14)0.0295 (3)
H15A0.30250.06870.36550.035*
H15B0.41330.10440.43980.035*
C160.47967 (16)0.06121 (3)0.59449 (14)0.0283 (3)
H16A0.41460.04090.61390.034*
H16B0.52620.07650.68750.034*
C170.63784 (16)0.04591 (3)0.56685 (14)0.0278 (3)
H17A0.70220.06620.54620.033*
H17B0.59140.03040.47460.033*
C180.77024 (16)0.02355 (3)0.70403 (14)0.0278 (3)
H18A0.81610.03900.79640.033*
H18B0.70600.00310.72430.033*
C190.92947 (16)0.00835 (3)0.67688 (14)0.0277 (3)
H19A0.88390.00790.58690.033*
H19B0.99100.02870.65270.033*
C201.06521 (16)0.01274 (3)0.81635 (14)0.0292 (3)
H20A1.11110.00360.90620.035*
H20B1.00350.03300.84080.035*
C211.22377 (17)0.02808 (3)0.78946 (14)0.0297 (3)
H21A1.28420.00790.76310.036*
H21B1.17820.04480.70090.036*
C221.36085 (17)0.04850 (4)0.93023 (15)0.0319 (3)
H22A1.30000.06850.95710.038*
H22B1.40700.03171.01850.038*
C231.51950 (17)0.06420 (4)0.90372 (14)0.0317 (3)
H23A1.57600.04450.87060.038*
H23B1.47440.08220.81990.038*
C241.66148 (17)0.08248 (3)1.04886 (14)0.0309 (3)
H24A1.70700.06441.13230.037*
H24B1.60450.10201.08240.037*
C251.81995 (17)0.09856 (4)1.02357 (15)0.0318 (3)
H25A1.77640.11840.94790.038*
H25B1.86960.07960.98000.038*
C261.96936 (17)0.11326 (3)1.17273 (15)0.0331 (3)
H26A2.01960.09291.24500.040*
H26B1.91740.13061.22100.040*
C272.1211 (2)0.13226 (5)1.1471 (2)0.0527 (4)
H27A2.21050.14081.24540.079*
H27B2.17550.11511.10170.079*
H27C2.07330.15281.07780.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0250 (5)0.0383 (5)0.0285 (5)0.0006 (4)0.0060 (4)0.0013 (4)
O20.0388 (6)0.0456 (5)0.0359 (5)0.0037 (4)0.0231 (4)0.0053 (4)
N10.0210 (5)0.0307 (5)0.0285 (5)0.0020 (4)0.0092 (4)0.0081 (4)
N20.0197 (5)0.0258 (5)0.0348 (5)0.0031 (4)0.0112 (4)0.0009 (4)
C10.0275 (6)0.0265 (6)0.0246 (5)0.0091 (5)0.0074 (5)0.0048 (4)
C20.0447 (8)0.0452 (8)0.0309 (7)0.0174 (6)0.0166 (6)0.0137 (6)
C30.0656 (11)0.0486 (9)0.0249 (7)0.0224 (8)0.0106 (7)0.0087 (6)
C40.0545 (10)0.0342 (7)0.0314 (7)0.0090 (7)0.0074 (7)0.0003 (6)
C50.0319 (7)0.0271 (6)0.0408 (7)0.0028 (5)0.0000 (6)0.0011 (5)
C60.0249 (6)0.0203 (5)0.0288 (6)0.0065 (4)0.0052 (5)0.0019 (4)
C70.0238 (7)0.0365 (7)0.0601 (9)0.0034 (5)0.0215 (7)0.0009 (6)
C80.0238 (6)0.0231 (5)0.0279 (6)0.0004 (4)0.0110 (5)0.0012 (4)
C90.0223 (6)0.0246 (5)0.0216 (5)0.0048 (4)0.0080 (4)0.0023 (4)
C100.0220 (6)0.0276 (5)0.0236 (5)0.0057 (4)0.0116 (5)0.0027 (4)
C110.0294 (7)0.0373 (7)0.0492 (8)0.0004 (5)0.0171 (6)0.0144 (6)
C120.0269 (6)0.0282 (6)0.0248 (5)0.0070 (5)0.0102 (5)0.0076 (4)
C130.0315 (7)0.0328 (6)0.0271 (6)0.0122 (5)0.0125 (5)0.0085 (5)
C140.0280 (6)0.0282 (6)0.0273 (6)0.0082 (5)0.0111 (5)0.0059 (5)
C150.0283 (7)0.0311 (6)0.0292 (6)0.0088 (5)0.0120 (5)0.0067 (5)
C160.0247 (6)0.0318 (6)0.0274 (6)0.0073 (5)0.0098 (5)0.0049 (5)
C170.0244 (6)0.0303 (6)0.0275 (6)0.0067 (5)0.0097 (5)0.0042 (5)
C180.0248 (6)0.0297 (6)0.0289 (6)0.0060 (5)0.0111 (5)0.0054 (5)
C190.0247 (6)0.0295 (6)0.0283 (6)0.0070 (5)0.0103 (5)0.0037 (5)
C200.0254 (6)0.0327 (6)0.0294 (6)0.0069 (5)0.0113 (5)0.0067 (5)
C210.0269 (6)0.0341 (6)0.0280 (6)0.0081 (5)0.0113 (5)0.0055 (5)
C220.0274 (7)0.0370 (7)0.0319 (6)0.0096 (5)0.0128 (5)0.0077 (5)
C230.0284 (7)0.0367 (6)0.0303 (6)0.0103 (5)0.0124 (5)0.0062 (5)
C240.0281 (7)0.0342 (6)0.0306 (6)0.0084 (5)0.0124 (5)0.0048 (5)
C250.0291 (7)0.0332 (6)0.0341 (6)0.0090 (5)0.0140 (6)0.0044 (5)
C260.0275 (7)0.0293 (6)0.0374 (7)0.0039 (5)0.0083 (6)0.0017 (5)
C270.0346 (8)0.0525 (9)0.0647 (10)0.0169 (7)0.0145 (8)0.0033 (8)
Geometric parameters (Å, º) top
O1—C101.2197 (14)C15—H15A0.9700
O2—C81.2206 (14)C15—H15B0.9700
N1—C101.3640 (14)C16—C171.5209 (16)
N1—C11.4235 (16)C16—H16A0.9700
N1—C111.4676 (16)C16—H16B0.9700
N2—C81.3676 (15)C17—C181.5254 (16)
N2—C61.4208 (15)C17—H17A0.9700
N2—C71.4690 (16)C17—H17B0.9700
C1—C61.3975 (18)C18—C191.5252 (16)
C1—C21.3976 (17)C18—H18A0.9700
C2—C31.380 (2)C18—H18B0.9700
C2—H20.9300C19—C201.5233 (16)
C3—C41.380 (2)C19—H19A0.9700
C3—H30.9300C19—H19B0.9700
C4—C51.382 (2)C20—C211.5207 (16)
C4—H40.9300C20—H20A0.9700
C5—C61.3964 (18)C20—H20B0.9700
C5—H50.9300C21—C221.5223 (17)
C7—H7A0.9600C21—H21A0.9700
C7—H7B0.9600C21—H21B0.9700
C7—H7C0.9600C22—C231.5244 (17)
C8—C91.5298 (16)C22—H22A0.9700
C9—C121.5230 (15)C22—H22B0.9700
C9—C101.5266 (16)C23—C241.5251 (17)
C9—H9A0.9800C23—H23A0.9700
C11—H11A0.9600C23—H23B0.9700
C11—H11B0.9600C24—C251.5222 (17)
C11—H11C0.9600C24—H24A0.9700
C12—C131.5264 (16)C24—H24B0.9700
C12—H12A0.9700C25—C261.5205 (17)
C12—H12B0.9700C25—H25A0.9700
C13—C141.5210 (16)C25—H25B0.9700
C13—H13A0.9700C26—C271.5196 (19)
C13—H13B0.9700C26—H26A0.9700
C14—C151.5248 (16)C26—H26B0.9700
C14—H14A0.9700C27—H27A0.9600
C14—H14B0.9700C27—H27B0.9600
C15—C161.5195 (16)C27—H27C0.9600
C10—N1—C1122.93 (10)C15—C16—C17113.69 (10)
C10—N1—C11117.97 (10)C15—C16—H16A108.8
C1—N1—C11118.81 (10)C17—C16—H16A108.8
C8—N2—C6123.12 (10)C15—C16—H16B108.8
C8—N2—C7117.24 (10)C17—C16—H16B108.8
C6—N2—C7119.16 (10)H16A—C16—H16B107.7
C6—C1—C2119.60 (12)C16—C17—C18113.56 (10)
C6—C1—N1121.90 (10)C16—C17—H17A108.9
C2—C1—N1118.48 (12)C18—C17—H17A108.9
C3—C2—C1120.87 (15)C16—C17—H17B108.9
C3—C2—H2119.6C18—C17—H17B108.9
C1—C2—H2119.6H17A—C17—H17B107.7
C4—C3—C2119.58 (14)C19—C18—C17113.64 (10)
C4—C3—H3120.2C19—C18—H18A108.8
C2—C3—H3120.2C17—C18—H18A108.8
C3—C4—C5120.28 (14)C19—C18—H18B108.8
C3—C4—H4119.9C17—C18—H18B108.8
C5—C4—H4119.9H18A—C18—H18B107.7
C4—C5—C6120.98 (14)C20—C19—C18113.56 (10)
C4—C5—H5119.5C20—C19—H19A108.9
C6—C5—H5119.5C18—C19—H19A108.9
C5—C6—C1118.67 (12)C20—C19—H19B108.9
C5—C6—N2119.41 (12)C18—C19—H19B108.9
C1—C6—N2121.91 (11)H19A—C19—H19B107.7
N2—C7—H7A109.5C21—C20—C19113.71 (10)
N2—C7—H7B109.5C21—C20—H20A108.8
H7A—C7—H7B109.5C19—C20—H20A108.8
N2—C7—H7C109.5C21—C20—H20B108.8
H7A—C7—H7C109.5C19—C20—H20B108.8
H7B—C7—H7C109.5H20A—C20—H20B107.7
O2—C8—N2121.78 (11)C20—C21—C22113.51 (10)
O2—C8—C9122.36 (11)C20—C21—H21A108.9
N2—C8—C9115.83 (10)C22—C21—H21A108.9
C12—C9—C10111.73 (10)C20—C21—H21B108.9
C12—C9—C8111.91 (9)C22—C21—H21B108.9
C10—C9—C8105.74 (9)H21A—C21—H21B107.7
C12—C9—H9A109.1C21—C22—C23113.81 (10)
C10—C9—H9A109.1C21—C22—H22A108.8
C8—C9—H9A109.1C23—C22—H22A108.8
O1—C10—N1121.80 (11)C21—C22—H22B108.8
O1—C10—C9122.55 (10)C23—C22—H22B108.8
N1—C10—C9115.60 (10)H22A—C22—H22B107.7
N1—C11—H11A109.5C22—C23—C24113.20 (10)
N1—C11—H11B109.5C22—C23—H23A108.9
H11A—C11—H11B109.5C24—C23—H23A108.9
N1—C11—H11C109.5C22—C23—H23B108.9
H11A—C11—H11C109.5C24—C23—H23B108.9
H11B—C11—H11C109.5H23A—C23—H23B107.8
C9—C12—C13112.87 (9)C25—C24—C23113.73 (10)
C9—C12—H12A109.0C25—C24—H24A108.8
C13—C12—H12A109.0C23—C24—H24A108.8
C9—C12—H12B109.0C25—C24—H24B108.8
C13—C12—H12B109.0C23—C24—H24B108.8
H12A—C12—H12B107.8H24A—C24—H24B107.7
C14—C13—C12112.94 (9)C26—C25—C24113.24 (10)
C14—C13—H13A109.0C26—C25—H25A108.9
C12—C13—H13A109.0C24—C25—H25A108.9
C14—C13—H13B109.0C26—C25—H25B108.9
C12—C13—H13B109.0C24—C25—H25B108.9
H13A—C13—H13B107.8H25A—C25—H25B107.7
C13—C14—C15113.52 (10)C27—C26—C25113.80 (12)
C13—C14—H14A108.9C27—C26—H26A108.8
C15—C14—H14A108.9C25—C26—H26A108.8
C13—C14—H14B108.9C27—C26—H26B108.8
C15—C14—H14B108.9C25—C26—H26B108.8
H14A—C14—H14B107.7H26A—C26—H26B107.7
C16—C15—C14113.04 (10)C26—C27—H27A109.5
C16—C15—H15A109.0C26—C27—H27B109.5
C14—C15—H15A109.0H27A—C27—H27B109.5
C16—C15—H15B109.0C26—C27—H27C109.5
C14—C15—H15B109.0H27A—C27—H27C109.5
H15A—C15—H15B107.8H27B—C27—H27C109.5
C10—N1—C1—C650.83 (16)N2—C8—C9—C1070.80 (12)
C11—N1—C1—C6135.46 (12)C1—N1—C10—O1177.18 (11)
C10—N1—C1—C2130.67 (12)C11—N1—C10—O13.42 (17)
C11—N1—C1—C243.04 (16)C1—N1—C10—C95.49 (16)
C6—C1—C2—C30.15 (19)C11—N1—C10—C9179.24 (10)
N1—C1—C2—C3178.69 (12)C12—C9—C10—O116.10 (15)
C1—C2—C3—C41.4 (2)C8—C9—C10—O1105.89 (12)
C2—C3—C4—C51.4 (2)C12—C9—C10—N1166.59 (9)
C3—C4—C5—C60.0 (2)C8—C9—C10—N171.43 (12)
C4—C5—C6—C11.23 (18)C10—C9—C12—C1368.09 (13)
C4—C5—C6—N2179.85 (11)C8—C9—C12—C13173.55 (10)
C2—C1—C6—C51.16 (17)C9—C12—C13—C14173.66 (10)
N1—C1—C6—C5177.32 (11)C12—C13—C14—C15178.37 (10)
C2—C1—C6—N2179.94 (11)C13—C14—C15—C16178.71 (11)
N1—C1—C6—N21.57 (17)C14—C15—C16—C17179.55 (10)
C8—N2—C6—C5132.06 (12)C15—C16—C17—C18179.34 (10)
C7—N2—C6—C539.70 (15)C16—C17—C18—C19179.70 (10)
C8—N2—C6—C149.05 (16)C17—C18—C19—C20177.81 (10)
C7—N2—C6—C1139.19 (12)C18—C19—C20—C21179.76 (10)
C6—N2—C8—O2176.04 (11)C19—C20—C21—C22178.91 (11)
C7—N2—C8—O24.13 (17)C20—C21—C22—C23179.57 (11)
C6—N2—C8—C96.17 (15)C21—C22—C23—C24176.41 (11)
C7—N2—C8—C9178.07 (10)C22—C23—C24—C25179.53 (11)
O2—C8—C9—C1214.88 (16)C23—C24—C25—C26174.22 (11)
N2—C8—C9—C12167.34 (10)C24—C25—C26—C27175.17 (12)
O2—C8—C9—C10106.98 (12)

Experimental details

Crystal data
Chemical formulaC27H44N2O2
Mr428.64
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)8.1426 (1), 36.2705 (5), 9.4090 (1)
β (°) 114.611 (1)
V3)2526.38 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.50 × 0.30 × 0.10
Data collection
DiffractometerBruker X8 APEXII
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
45223, 7353, 5105
Rint0.036
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.159, 1.03
No. of reflections7353
No. of parameters282
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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

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. (2011). Acta Cryst. E67, o674.  Web of Science CSD CrossRef IUCr Journals 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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Volume 67| Part 5| May 2011| Page o1155
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