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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3149.
Published online 2009 November 21. doi:  10.1107/S1600536809048508
PMCID: PMC2971782

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

Abstract

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 [triangle]).

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Object name is e-65-o3149-scheme1.jpg

Experimental

Crystal data

  • C26H22N2O2
  • M r = 394.46
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3149-efi1.jpg
  • 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)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 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 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048508/sj2679sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048508/sj2679Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

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

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).

Figures

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.

Crystal data

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

Bruker APEXII diffractometer3931 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
graphiteθmax = 27.5°, θmin = 2.0°
[var phi] and ω scansh = −11→11
29296 measured reflectionsk = −24→18
4750 independent reflectionsl = −16→15

Refinement

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 = 1.02w = 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

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

xyzUiso*/UeqOcc. (<1)
O10.17022 (9)0.29934 (4)0.63891 (7)0.0310 (2)
O2−0.09780 (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*
C4−0.00697 (13)0.38106 (6)0.49721 (9)0.0285 (2)
H4A−0.06460.34610.53980.034*
H4B−0.07870.41780.47010.034*
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)
H20A−0.03270.52350.82950.038*
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)

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, °)

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—O1−176.41 (10)C1—N1—C13—C1487.11 (17)
C13—N1—C1—O1−0.01 (16)C7—N1—C13—C14−96.30 (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—O2−176.15 (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—C3−162.38 (9)C19'—C14'—C15'—C16'0.0
O2—C2—C3—C414.32 (15)C14'—C15'—C16'—C17'0.0
N2—C2—C3—C4−170.04 (9)C15'—C16'—C17'—C18'0.0
O2—C2—C3—C1−105.49 (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—C2−76.66 (11)C15'—C14'—C19'—C18'0.0
O1—C1—C3—C4−18.46 (15)C14'—C13—C14—C19175 (5)
N1—C1—C3—C4164.24 (9)N1—C13—C14—C19−41.8 (3)
C2—C3—C4—C5176.83 (9)C14'—C13—C14—C15−3(4)
C1—C3—C4—C5−68.12 (12)N1—C13—C14—C15140.1 (2)
C1—N1—C7—C12−137.80 (11)C19—C14—C15—C16−0.8 (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—C8−130.69 (11)C15—C16—C17—C180.2 (3)
C12—C7—C8—C91.77 (16)C16—C17—C18—C19−0.8 (4)
N1—C7—C8—C9178.23 (10)C15—C14—C19—C180.2 (3)
C12—C7—C8—N2−176.05 (10)C13—C14—C19—C18−177.9 (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—C9−58.95 (14)C8—N2—C20—C21−71.84 (13)
C2—N2—C8—C7−51.91 (15)N2—C20—C21—C26110.77 (13)
C20—N2—C8—C7118.89 (11)N2—C20—C21—C22−67.23 (15)
C7—C8—C9—C10−2.35 (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—C25−0.7 (2)
C10—C11—C12—C7−2.03 (19)C23—C24—C25—C260.2 (2)
C8—C7—C12—C110.40 (17)C22—C21—C26—C25−0.5 (2)
N1—C7—C12—C11−176.12 (10)C20—C21—C26—C25−178.52 (13)
C1—N1—C13—C14'93.9 (7)C24—C25—C26—C210.4 (2)
C7—N1—C13—C14'−89.5 (7)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2679).

References

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