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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

1,5-Di­benzyl-3-propargyl-1,5-benzo­diazepine-2,4-dione

aLaboratoire de Chimie Organique Appliquée, Faculté des Sciences et Techniques, Université Sidi Mohamed Ben Abdallah, Fés, Morocco, bLaboratoire de Hétérochimie Fondamentale et Appliquée, Université Paul Sabatier, 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, C26H22N2O2, features a benzene ring fused with a seven-membered diazepine ring; the latter ring adopts a boat conformation (with the propargylallyl-bearing C atom as the prow and the fused-ring C atoms as the stern). The phenyl ring of one of the two benzyl substituents is disordered over two positions in a 0.812 (11):0.188 (11) ratio.

Related literature

For the crystal structure of the parent compound, benzodiazepin-2,4-dione, see: Négrier et al. (2006[Négrier, Ph., Mondieig, D., Léger, J. M., Benali, B., Lazar, Z., Boucetta, A., Elassyry, A., Lakhrissi, B., Jermoumi, C. & Massoui, M. (2006). Anal. Sci. X-ray Struct. Anal. Online, 22, 175.]).

[Scheme 1]

Experimental

Crystal data
  • C26H22N2O2

  • Mr = 394.46

  • Monoclinic, P 21 /c

  • a = 8.8663 (2) Å

  • b = 18.6771 (4) Å

  • c = 12.4665 (3) Å

  • β = 91.154 (1)°

  • V = 2063.99 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 193 K

  • 0.70 × 0.50 × 0.30 mm

Data collection
  • Bruker APEXII diffractometer

  • Absorption correction: none

  • 29296 measured reflections

  • 4750 independent reflections

  • 3931 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.112

  • S = 1.02

  • 4750 reflections

  • 278 parameters

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). 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, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


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 propargyl 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.

A somewhat large crystal was used in the diffraction measurements.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 1.00 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C).

One of the phenyl rings is disordered over two positions. This was refined as two rigid hexagons of 1.39 Å sides. The temperature factors of the primed atoms were restrained to those of the unprimed ones. The minor component refined to 0.188 (11).

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
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C26H22N2O2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in one of the phenyl rings is not shown.
1,5-Dibenzyl-3-propargyl-1,5-benzodiazepine-2,4-dione top
Crystal data top
C26H22N2O2F(000) = 832
Mr = 394.46Dx = 1.269 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9973 reflections
a = 8.8663 (2) Åθ = 2.5–32.9°
b = 18.6771 (4) ŵ = 0.08 mm1
c = 12.4665 (3) ÅT = 193 K
β = 91.154 (1)°Irregular block, colorless
V = 2063.99 (8) Å30.70 × 0.50 × 0.30 mm
Z = 4
Data collection top
Bruker APEXII
diffractometer
3931 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 27.5°, θmin = 2.0°
ϕ and ω scansh = 1111
29296 measured reflectionsk = 2418
4750 independent reflectionsl = 1615
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0579P)2 + 0.5557P]
where P = (Fo2 + 2Fc2)/3
4750 reflections(Δ/σ)max = 0.001
278 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C26H22N2O2V = 2063.99 (8) Å3
Mr = 394.46Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.8663 (2) ŵ = 0.08 mm1
b = 18.6771 (4) ÅT = 193 K
c = 12.4665 (3) Å0.70 × 0.50 × 0.30 mm
β = 91.154 (1)°
Data collection top
Bruker APEXII
diffractometer
3931 reflections with I > 2σ(I)
29296 measured reflectionsRint = 0.027
4750 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.112H-atom parameters constrained
S = 1.02Δρmax = 0.26 e Å3
4750 reflectionsΔρmin = 0.27 e Å3
278 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.17022 (9)0.29934 (4)0.63891 (7)0.0310 (2)
O20.09780 (10)0.44893 (5)0.68067 (8)0.0408 (2)
N10.34007 (10)0.38740 (5)0.67524 (7)0.0250 (2)
N20.12855 (11)0.50134 (5)0.71936 (7)0.0264 (2)
C10.20965 (12)0.36186 (6)0.62971 (8)0.0238 (2)
C20.03474 (13)0.45816 (6)0.66023 (9)0.0268 (2)
C30.11097 (12)0.41712 (6)0.57026 (8)0.0238 (2)
H30.17530.45010.52770.029*
C40.00697 (13)0.38106 (6)0.49721 (9)0.0285 (2)
H4A0.06460.34610.53980.034*
H4B0.07870.41780.47010.034*
C50.05908 (14)0.34408 (7)0.40583 (10)0.0334 (3)
C60.11070 (17)0.31415 (8)0.33138 (12)0.0461 (3)
H60.15210.29010.27160.055*
C70.38435 (13)0.46069 (6)0.67074 (8)0.0249 (2)
C80.28132 (13)0.51554 (6)0.69185 (8)0.0255 (2)
C90.33036 (15)0.58677 (7)0.68953 (10)0.0332 (3)
H90.26050.62440.70110.040*
C100.47975 (16)0.60272 (7)0.67056 (10)0.0384 (3)
H100.51220.65120.67000.046*
C110.58233 (15)0.54818 (7)0.65236 (10)0.0369 (3)
H110.68530.55930.64100.044*
C120.53473 (14)0.47752 (7)0.65072 (9)0.0314 (3)
H120.60460.44040.63590.038*
C130.43658 (14)0.33760 (7)0.73776 (10)0.0320 (3)
H13A0.47960.36490.79910.038*0.188 (11)
H13B0.36950.30080.76810.038*0.188 (11)
H13C0.37150.30280.77480.038*0.812 (11)
H13D0.49300.36500.79340.038*0.812 (11)
C14'0.5525 (9)0.3026 (8)0.6915 (10)0.0290 (5)0.188 (11)
C15'0.6972 (11)0.3031 (7)0.7365 (9)0.0426 (6)0.188 (11)
H15'0.71730.32900.80080.051*0.188 (11)
C16'0.8126 (8)0.2659 (7)0.6873 (11)0.0480 (10)0.188 (11)
H16'0.91150.26630.71800.058*0.188 (11)
C17'0.7832 (12)0.2281 (6)0.5931 (12)0.0511 (8)0.188 (11)
H17'0.86210.20260.55950.061*0.188 (11)
C18'0.6385 (14)0.2275 (8)0.5482 (12)0.0728 (9)0.188 (11)
H18'0.61840.20170.48380.087*0.188 (11)
C19'0.5231 (10)0.2648 (9)0.5974 (11)0.0567 (7)0.188 (11)
H19'0.42420.26440.56670.068*0.188 (11)
C140.5505 (2)0.29604 (17)0.6685 (3)0.0290 (5)0.812 (11)
C150.6962 (2)0.28451 (19)0.7075 (3)0.0426 (6)0.812 (11)
H150.72610.30390.77510.051*0.812 (11)
C160.7990 (2)0.2450 (2)0.6492 (4)0.0480 (10)0.812 (11)
H160.89790.23730.67750.058*0.812 (11)
C170.7587 (3)0.21739 (14)0.5519 (4)0.0511 (8)0.812 (11)
H170.82880.19030.51210.061*0.812 (11)
C180.6154 (3)0.22919 (19)0.5119 (4)0.0728 (9)0.812 (11)
H180.58700.21050.44360.087*0.812 (11)
C190.5119 (3)0.2679 (2)0.5699 (3)0.0567 (7)0.812 (11)
H190.41310.27520.54120.068*0.812 (11)
C200.07850 (14)0.52656 (7)0.82584 (9)0.0313 (3)
H20A0.03270.52350.82950.038*
H20B0.10830.57720.83650.038*
C210.15023 (14)0.48060 (7)0.91273 (9)0.0305 (3)
C220.11027 (17)0.40885 (7)0.92212 (10)0.0396 (3)
H220.03540.38930.87510.047*
C230.17857 (19)0.36561 (8)0.99950 (12)0.0482 (4)
H230.15110.31661.00480.058*
C240.28666 (18)0.39393 (9)1.06888 (11)0.0505 (4)
H240.33270.36451.12240.061*
C250.32761 (19)0.46476 (10)1.06047 (12)0.0522 (4)
H250.40210.48411.10800.063*
C260.25989 (16)0.50798 (8)0.98237 (11)0.0415 (3)
H260.28900.55680.97670.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0302 (4)0.0243 (4)0.0384 (4)0.0013 (3)0.0020 (3)0.0049 (3)
O20.0226 (4)0.0483 (6)0.0516 (6)0.0013 (4)0.0039 (4)0.0121 (4)
N10.0235 (5)0.0243 (5)0.0272 (4)0.0033 (4)0.0028 (4)0.0014 (3)
N20.0249 (5)0.0275 (5)0.0269 (5)0.0028 (4)0.0014 (4)0.0024 (4)
C10.0232 (5)0.0249 (5)0.0233 (5)0.0015 (4)0.0013 (4)0.0008 (4)
C20.0236 (6)0.0262 (5)0.0306 (5)0.0040 (4)0.0011 (4)0.0010 (4)
C30.0239 (5)0.0228 (5)0.0246 (5)0.0006 (4)0.0020 (4)0.0015 (4)
C40.0272 (6)0.0279 (6)0.0302 (5)0.0007 (4)0.0063 (4)0.0013 (4)
C50.0338 (6)0.0305 (6)0.0355 (6)0.0041 (5)0.0096 (5)0.0020 (5)
C60.0457 (8)0.0493 (8)0.0430 (7)0.0003 (7)0.0068 (6)0.0156 (6)
C70.0257 (5)0.0264 (5)0.0225 (5)0.0006 (4)0.0021 (4)0.0012 (4)
C80.0251 (6)0.0279 (5)0.0234 (5)0.0006 (4)0.0018 (4)0.0010 (4)
C90.0369 (7)0.0268 (6)0.0358 (6)0.0002 (5)0.0030 (5)0.0029 (5)
C100.0424 (7)0.0309 (6)0.0417 (7)0.0111 (5)0.0010 (6)0.0012 (5)
C110.0301 (6)0.0435 (7)0.0371 (6)0.0114 (5)0.0023 (5)0.0031 (5)
C120.0260 (6)0.0363 (6)0.0318 (6)0.0005 (5)0.0013 (4)0.0035 (5)
C130.0311 (6)0.0324 (6)0.0322 (6)0.0037 (5)0.0096 (5)0.0045 (5)
C14'0.0251 (6)0.0232 (8)0.0384 (13)0.0018 (5)0.0039 (7)0.0042 (8)
C15'0.0285 (7)0.0577 (15)0.0414 (14)0.0039 (9)0.0049 (8)0.0094 (11)
C16'0.0246 (8)0.0538 (16)0.066 (2)0.0098 (9)0.0024 (10)0.0223 (16)
C17'0.0350 (11)0.0326 (9)0.086 (2)0.0053 (8)0.0170 (12)0.0031 (11)
C18'0.0433 (12)0.0895 (15)0.086 (2)0.0116 (11)0.0022 (13)0.0534 (17)
C19'0.0300 (8)0.0751 (12)0.0647 (18)0.0138 (8)0.0097 (9)0.0338 (14)
C140.0251 (6)0.0232 (8)0.0384 (13)0.0018 (5)0.0039 (7)0.0042 (8)
C150.0285 (7)0.0577 (15)0.0414 (14)0.0039 (9)0.0049 (8)0.0094 (11)
C160.0246 (8)0.0538 (16)0.066 (2)0.0098 (9)0.0024 (10)0.0223 (16)
C170.0350 (11)0.0326 (9)0.086 (2)0.0053 (8)0.0170 (12)0.0031 (11)
C180.0433 (12)0.0895 (15)0.086 (2)0.0116 (11)0.0022 (13)0.0534 (17)
C190.0300 (8)0.0751 (12)0.0647 (18)0.0138 (8)0.0097 (9)0.0338 (14)
C200.0313 (6)0.0314 (6)0.0313 (6)0.0061 (5)0.0046 (5)0.0057 (5)
C210.0294 (6)0.0350 (6)0.0273 (5)0.0027 (5)0.0070 (4)0.0035 (4)
C220.0442 (8)0.0391 (7)0.0355 (6)0.0043 (6)0.0008 (5)0.0016 (5)
C230.0620 (10)0.0395 (7)0.0433 (7)0.0013 (7)0.0074 (7)0.0067 (6)
C240.0524 (9)0.0622 (10)0.0369 (7)0.0101 (8)0.0009 (6)0.0118 (7)
C250.0473 (9)0.0694 (10)0.0394 (7)0.0062 (8)0.0092 (6)0.0018 (7)
C260.0430 (8)0.0436 (7)0.0378 (7)0.0062 (6)0.0010 (6)0.0024 (6)
Geometric parameters (Å, º) top
O1—C11.2248 (13)C15'—C16'1.3900
O2—C21.2197 (15)C15'—H15'0.9500
N1—C11.3640 (14)C16'—C17'1.3900
N1—C71.4254 (14)C16'—H16'0.9500
N1—C131.4758 (14)C17'—C18'1.3900
N2—C21.3641 (15)C17'—H17'0.9500
N2—C81.4288 (15)C18'—C19'1.3900
N2—C201.4847 (14)C18'—H18'0.9500
C1—C31.5342 (14)C19'—H19'0.9500
C2—C31.5274 (15)C14—C191.373 (2)
C3—C41.5291 (15)C14—C151.388 (2)
C3—H31.0000C15—C161.389 (3)
C4—C51.4645 (18)C15—H150.9500
C4—H4A0.9900C16—C171.359 (3)
C4—H4B0.9900C16—H160.9500
C5—C61.1833 (19)C17—C181.373 (3)
C6—H60.9500C17—H170.9500
C7—C121.3972 (17)C18—C191.384 (3)
C7—C81.4010 (16)C18—H180.9500
C8—C91.4001 (17)C19—H190.9500
C9—C101.3826 (19)C20—C211.5122 (17)
C9—H90.9500C20—H20A0.9900
C10—C111.387 (2)C20—H20B0.9900
C10—H100.9500C21—C261.3880 (18)
C11—C121.3856 (18)C21—C221.3918 (18)
C11—H110.9500C22—C231.388 (2)
C12—H120.9500C22—H220.9500
C13—C14'1.356 (8)C23—C241.383 (2)
C13—C141.550 (3)C23—H230.9500
C13—H13A0.9900C24—C251.376 (2)
C13—H13B0.9900C24—H240.9500
C13—H13C0.9900C25—C261.392 (2)
C13—H13D0.9900C25—H250.9500
C14'—C15'1.3900C26—H260.9500
C14'—C19'1.3900
C1—N1—C7123.46 (9)C13—C14'—C15'121.8 (7)
C1—N1—C13118.49 (9)C13—C14'—C19'118.2 (7)
C7—N1—C13117.96 (9)C15'—C14'—C19'120.0
C2—N2—C8123.41 (9)C14'—C15'—C16'120.0
C2—N2—C20118.73 (10)C14'—C15'—H15'120.0
C8—N2—C20117.23 (9)C16'—C15'—H15'120.0
O1—C1—N1122.39 (10)C15'—C16'—C17'120.0
O1—C1—C3121.70 (10)C15'—C16'—H16'120.0
N1—C1—C3115.86 (9)C17'—C16'—H16'120.0
O2—C2—N2123.38 (11)C18'—C17'—C16'120.0
O2—C2—C3121.66 (10)C18'—C17'—H17'120.0
N2—C2—C3114.81 (10)C16'—C17'—H17'120.0
C2—C3—C4110.55 (9)C19'—C18'—C17'120.0
C2—C3—C1103.86 (8)C19'—C18'—H18'120.0
C4—C3—C1111.59 (9)C17'—C18'—H18'120.0
C2—C3—H3110.2C18'—C19'—C14'120.0
C4—C3—H3110.2C18'—C19'—H19'120.0
C1—C3—H3110.2C14'—C19'—H19'120.0
C5—C4—C3113.06 (10)C19—C14—C15117.86 (16)
C5—C4—H4A109.0C19—C14—C13122.45 (17)
C3—C4—H4A109.0C15—C14—C13119.66 (16)
C5—C4—H4B109.0C14—C15—C16120.98 (18)
C3—C4—H4B109.0C14—C15—H15119.5
H4A—C4—H4B107.8C16—C15—H15119.5
C6—C5—C4179.17 (14)C17—C16—C15120.36 (17)
C5—C6—H6180.0C17—C16—H16119.8
C12—C7—C8119.81 (10)C15—C16—H16119.8
C12—C7—N1119.19 (10)C16—C17—C18119.18 (18)
C8—C7—N1120.91 (10)C16—C17—H17120.4
C9—C8—C7119.14 (11)C18—C17—H17120.4
C9—C8—N2118.53 (10)C17—C18—C19120.8 (2)
C7—C8—N2122.29 (10)C17—C18—H18119.6
C10—C9—C8120.48 (12)C19—C18—H18119.6
C10—C9—H9119.8C14—C19—C18120.79 (18)
C8—C9—H9119.8C14—C19—H19119.6
C9—C10—C11120.21 (12)C18—C19—H19119.6
C9—C10—H10119.9N2—C20—C21109.35 (9)
C11—C10—H10119.9N2—C20—H20A109.8
C12—C11—C10120.08 (12)C21—C20—H20A109.8
C12—C11—H11120.0N2—C20—H20B109.8
C10—C11—H11120.0C21—C20—H20B109.8
C11—C12—C7120.21 (12)H20A—C20—H20B108.3
C11—C12—H12119.9C26—C21—C22118.58 (12)
C7—C12—H12119.9C26—C21—C20121.21 (12)
C14'—C13—N1121.1 (6)C22—C21—C20120.18 (11)
N1—C13—C14113.51 (14)C23—C22—C21120.70 (13)
C14'—C13—H13A107.1C23—C22—H22119.7
N1—C13—H13A107.1C21—C22—H22119.7
C14—C13—H13A116.3C24—C23—C22119.96 (14)
C14'—C13—H13B107.1C24—C23—H23120.0
N1—C13—H13B107.1C22—C23—H23120.0
C14—C13—H13B105.6C25—C24—C23120.03 (14)
H13A—C13—H13B106.8C25—C24—H24120.0
C14'—C13—H13C109.6C23—C24—H24120.0
N1—C13—H13C108.9C24—C25—C26120.00 (14)
C14—C13—H13C108.9C24—C25—H25120.0
H13A—C13—H13C101.4C26—C25—H25120.0
N1—C13—H13D108.9C21—C26—C25120.73 (14)
C14—C13—H13D108.9C21—C26—H26119.6
H13C—C13—H13D107.7C25—C26—H26119.6
C7—N1—C1—O1176.41 (10)C1—N1—C13—C1487.11 (17)
C13—N1—C1—O10.01 (16)C7—N1—C13—C1496.30 (16)
C7—N1—C1—C30.87 (15)N1—C13—C14'—C15'128.9 (7)
C13—N1—C1—C3177.26 (9)C14—C13—C14'—C15'169 (5)
C8—N2—C2—O2176.15 (11)N1—C13—C14'—C19'51.8 (9)
C20—N2—C2—O213.17 (17)C14—C13—C14'—C19'11 (4)
C8—N2—C2—C38.29 (15)C13—C14'—C15'—C16'179.3 (12)
C20—N2—C2—C3162.38 (9)C19'—C14'—C15'—C16'0.0
O2—C2—C3—C414.32 (15)C14'—C15'—C16'—C17'0.0
N2—C2—C3—C4170.04 (9)C15'—C16'—C17'—C18'0.0
O2—C2—C3—C1105.49 (12)C16'—C17'—C18'—C19'0.0
N2—C2—C3—C170.14 (11)C17'—C18'—C19'—C14'0.0
O1—C1—C3—C2100.64 (12)C13—C14'—C19'—C18'179.3 (12)
N1—C1—C3—C276.66 (11)C15'—C14'—C19'—C18'0.0
O1—C1—C3—C418.46 (15)C14'—C13—C14—C19175 (5)
N1—C1—C3—C4164.24 (9)N1—C13—C14—C1941.8 (3)
C2—C3—C4—C5176.83 (9)C14'—C13—C14—C153 (4)
C1—C3—C4—C568.12 (12)N1—C13—C14—C15140.1 (2)
C1—N1—C7—C12137.80 (11)C19—C14—C15—C160.8 (3)
C13—N1—C7—C1245.79 (14)C13—C14—C15—C16177.4 (2)
C1—N1—C7—C845.72 (15)C14—C15—C16—C170.6 (3)
C13—N1—C7—C8130.69 (11)C15—C16—C17—C180.2 (3)
C12—C7—C8—C91.77 (16)C16—C17—C18—C190.8 (4)
N1—C7—C8—C9178.23 (10)C15—C14—C19—C180.2 (3)
C12—C7—C8—N2176.05 (10)C13—C14—C19—C18177.9 (3)
N1—C7—C8—N20.41 (15)C17—C18—C19—C140.6 (4)
C2—N2—C8—C9130.25 (12)C2—N2—C20—C2199.41 (12)
C20—N2—C8—C958.95 (14)C8—N2—C20—C2171.84 (13)
C2—N2—C8—C751.91 (15)N2—C20—C21—C26110.77 (13)
C20—N2—C8—C7118.89 (11)N2—C20—C21—C2267.23 (15)
C7—C8—C9—C102.35 (17)C26—C21—C22—C230.0 (2)
N2—C8—C9—C10175.55 (11)C20—C21—C22—C23178.08 (12)
C8—C9—C10—C110.75 (19)C21—C22—C23—C240.6 (2)
C9—C10—C11—C121.46 (19)C22—C23—C24—C250.7 (2)
C10—C11—C12—C72.03 (19)C23—C24—C25—C260.2 (2)
C8—C7—C12—C110.40 (17)C22—C21—C26—C250.5 (2)
N1—C7—C12—C11176.12 (10)C20—C21—C26—C25178.52 (13)
C1—N1—C13—C14'93.9 (7)C24—C25—C26—C210.4 (2)
C7—N1—C13—C14'89.5 (7)

Experimental details

Crystal data
Chemical formulaC26H22N2O2
Mr394.46
Crystal system, space groupMonoclinic, P21/c
Temperature (K)193
a, b, c (Å)8.8663 (2), 18.6771 (4), 12.4665 (3)
β (°) 91.154 (1)
V3)2063.99 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.70 × 0.50 × 0.30
Data collection
DiffractometerBruker APEXII
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
29296, 4750, 3931
Rint0.027
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.112, 1.02
No. of reflections4750
No. of parameters278
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.27

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

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationNégrier, Ph., Mondieig, D., Léger, J. M., Benali, B., Lazar, Z., Boucetta, A., Elassyry, A., Lakhrissi, B., Jermoumi, C. & Massoui, M. (2006). Anal. Sci. X-ray Struct. Anal. Online, 22, 175.  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. (2009). publCIF. In preparation.  Google Scholar

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