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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

1-Benzyl-3-[(di­methyl­amino)methyl­ene]-4-phenyl-1H-1,4-benzodiazepin-2(3H)-one

aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, bInstitute of Nanomaterials and Nanotechnology, Avenue de l'Armée Royale, Madinat El Irfane, 10100 Rabat, Morocco, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 7 August 2009; accepted 11 August 2009; online 15 August 2009)

The title compound, C25H23N3O, features a benzene ring fused with a seven-membered 1,4-diazepine ring; the latter ring adopts a boat conformation with the (dimethyl­amino)methyl-bearing C atom as the prow and the fused-ring C atoms as the stern. There are two independent mol­ecules in the asymmetric unit with similar conformations.

Related literature

1,5-Benzodiazepines are synthons for other heterocyclic compounds; for the crystal structure of related 1,5-benzodiazepines, see: Doubia et al. (2007a[Doubia, M. L., Bouhfid, R., Ahabchane, N. H., Essassi, E. M. & El Ammari, L. (2007a). Acta Cryst. E63, o3305.],b[Doubia, M. L., Bouhfid, R., Ahabchane, N. H., Essassi, E. M. & El Ammari, L. (2007b). Acta Cryst. E63, o3306.]).

[Scheme 1]

Experimental

Crystal data
  • C25H23N3O

  • Mr = 381.46

  • Monoclinic, P 21

  • a = 8.9733 (3) Å

  • b = 26.3103 (7) Å

  • c = 9.9312 (3) Å

  • β = 115.644 (1)°

  • V = 2113.7 (1) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 293 K

  • 0.3 × 0.3 × 0.3 mm

Data collection
  • Bruker APEX2 diffractometer

  • Absorption correction: none

  • 25753 measured reflections

  • 4959 independent reflections

  • 4091 reflections with I > 2σ(I)

  • Rint = 0.038

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.118

  • S = 1.03

  • 4959 reflections

  • 527 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.17 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

1,5-Benzodiazepines are synthons for other heterocyclic compounds; for the crystal structure of related 1,5-benzodiazepines, see: Doubia et al. (2007a,b).

Experimental top

A mixture of 1-benzyl-4-phenyl-1,5-benzodiazepin-2-one (1 g, 3.06 mmol) and dimethylformamide-dimethylacetal (1.23 ml, 9.18 mmol) was heated at 413 K for 4 h. The product was recrystallized from ethanol to give yellow crystals.

Refinement top

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

In the absence of significant anomalous scattering effects, 4583 Friedel pairs were averaged in the final refinement.

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 the two independent molecules of C25H23N3O at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
1-Benzyl-3-[(dimethylamino)methylene]-4-phenyl-1H- 1,4-benzodiazepin-2(3H)-one top
Crystal data top
C25H23N3OF(000) = 808
Mr = 381.46Dx = 1.199 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 9099 reflections
a = 8.9733 (3) Åθ = 2.3–28.2°
b = 26.3103 (7) ŵ = 0.07 mm1
c = 9.9312 (3) ÅT = 293 K
β = 115.644 (1)°Block, yellow
V = 2113.7 (1) Å30.3 × 0.3 × 0.3 mm
Z = 4
Data collection top
Bruker APEX2
diffractometer
4091 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
Graphite monochromatorθmax = 27.5°, θmin = 2.3°
ϕ and ω scansh = 1111
25753 measured reflectionsk = 3334
4959 independent reflectionsl = 1212
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0708P)2 + 0.1173P]
where P = (Fo2 + 2Fc2)/3
4959 reflections(Δ/σ)max = 0.001
527 parametersΔρmax = 0.25 e Å3
1 restraintΔρmin = 0.17 e Å3
Crystal data top
C25H23N3OV = 2113.7 (1) Å3
Mr = 381.46Z = 4
Monoclinic, P21Mo Kα radiation
a = 8.9733 (3) ŵ = 0.07 mm1
b = 26.3103 (7) ÅT = 293 K
c = 9.9312 (3) Å0.3 × 0.3 × 0.3 mm
β = 115.644 (1)°
Data collection top
Bruker APEX2
diffractometer
4091 reflections with I > 2σ(I)
25753 measured reflectionsRint = 0.038
4959 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0431 restraint
wR(F2) = 0.118H-atom parameters constrained
S = 1.03Δρmax = 0.25 e Å3
4959 reflectionsΔρmin = 0.17 e Å3
527 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.4567 (3)0.50001 (9)0.2429 (3)0.0798 (8)
O20.0517 (2)0.22010 (11)0.2356 (2)0.0676 (7)
N10.7169 (3)0.47041 (9)0.3628 (3)0.0533 (6)
N20.7751 (3)0.38557 (8)0.2028 (3)0.0442 (5)
N30.2708 (3)0.35681 (10)0.1081 (3)0.0594 (6)
N40.2245 (2)0.21276 (8)0.3724 (2)0.0389 (4)
N50.3779 (2)0.14267 (8)0.2472 (2)0.0387 (4)
N60.0202 (3)0.18176 (10)0.1543 (2)0.0542 (6)
C10.7741 (4)0.52148 (12)0.4267 (4)0.0659 (9)
H1A0.76460.52440.52000.079*
H1B0.70230.54690.35870.079*
C20.9491 (4)0.53244 (11)0.4550 (3)0.0554 (7)
C31.0522 (6)0.55963 (16)0.5788 (5)0.0892 (13)
H31.01400.56970.64800.107*
C41.2105 (7)0.5723 (2)0.6026 (7)0.120 (2)
H41.27710.59080.68710.144*
C51.2692 (6)0.5583 (2)0.5057 (7)0.1061 (17)
H51.37600.56720.52220.127*
C61.1719 (5)0.53067 (18)0.3822 (5)0.0850 (11)
H61.21280.52040.31500.102*
C71.0129 (4)0.51803 (13)0.3574 (4)0.0646 (8)
H70.94740.49940.27280.077*
C80.8150 (3)0.42770 (10)0.4385 (3)0.0462 (6)
C90.8904 (4)0.42662 (13)0.5933 (4)0.0609 (8)
H90.87120.45290.64640.073*
C100.9937 (4)0.38716 (15)0.6696 (4)0.0653 (8)
H101.04240.38670.77340.078*
C111.0243 (4)0.34859 (13)0.5920 (4)0.0584 (7)
H111.09340.32190.64340.070*
C120.9533 (3)0.34936 (11)0.4390 (3)0.0475 (6)
H120.97850.32380.38740.057*
C130.8435 (3)0.38794 (9)0.3592 (3)0.0404 (5)
C140.6213 (3)0.39644 (10)0.1254 (3)0.0426 (6)
C150.5592 (3)0.39494 (11)0.0400 (3)0.0507 (7)
C160.6396 (4)0.36447 (14)0.1030 (4)0.0643 (8)
H160.72460.34300.04270.077*
C170.5928 (6)0.36622 (19)0.2549 (5)0.0898 (14)
H170.64710.34610.29670.108*
C180.4649 (7)0.3979 (2)0.3453 (5)0.0981 (16)
H180.43480.39930.44740.118*
C190.3842 (6)0.4266 (2)0.2859 (5)0.0903 (14)
H190.29750.44740.34730.108*
C200.4305 (4)0.42525 (15)0.1321 (4)0.0696 (9)
H200.37390.44500.09180.084*
C210.5079 (3)0.41522 (11)0.1880 (3)0.0473 (6)
C220.5557 (3)0.46494 (11)0.2668 (4)0.0531 (7)
C230.3567 (3)0.39855 (12)0.1694 (3)0.0522 (7)
H230.30300.42070.20690.063*
C240.1156 (4)0.34505 (16)0.1107 (5)0.0756 (10)
H24A0.08190.37310.15300.113*
H24B0.12790.31520.17030.113*
H24C0.03350.33900.01070.113*
C250.3329 (4)0.31667 (13)0.0448 (4)0.0618 (8)
H25A0.45150.31700.09180.093*
H25B0.29380.32220.06060.093*
H25C0.29410.28430.06140.093*
C260.2094 (3)0.22775 (11)0.5084 (3)0.0433 (6)
H26A0.10390.21600.50170.052*
H26B0.21080.26450.51510.052*
C270.3454 (3)0.20659 (10)0.6471 (3)0.0385 (5)
C280.4192 (4)0.23647 (11)0.7735 (3)0.0506 (7)
H280.38950.27050.76940.061*
C290.5365 (4)0.21660 (14)0.9058 (3)0.0643 (8)
H290.58440.23710.99000.077*
C300.5822 (4)0.16642 (15)0.9128 (3)0.0644 (8)
H300.65910.15271.00240.077*
C310.5143 (4)0.13667 (13)0.7877 (4)0.0630 (8)
H310.54750.10300.79160.076*
C320.3955 (4)0.15661 (10)0.6542 (3)0.0507 (6)
H320.34980.13620.56960.061*
C330.3757 (3)0.22508 (9)0.3639 (2)0.0344 (5)
C340.4547 (3)0.27062 (10)0.4213 (3)0.0414 (5)
H340.40930.29300.46590.050*
C350.6004 (3)0.28346 (11)0.4134 (3)0.0470 (6)
H350.65180.31430.45140.056*
C360.6686 (3)0.24983 (11)0.3485 (3)0.0462 (6)
H360.76530.25840.34100.055*
C370.5936 (3)0.20385 (11)0.2952 (3)0.0414 (5)
H370.64300.18100.25550.050*
C380.4454 (3)0.19078 (9)0.2991 (2)0.0346 (5)
C390.2219 (3)0.13862 (9)0.1633 (2)0.0347 (5)
C400.1538 (3)0.08647 (10)0.1183 (3)0.0399 (5)
C410.2590 (4)0.04589 (12)0.1369 (4)0.0618 (8)
H410.37230.05130.17470.074*
C420.1952 (5)0.00297 (13)0.0990 (5)0.0770 (10)
H420.26650.03020.11260.092*
C430.0313 (5)0.01128 (13)0.0430 (4)0.0743 (10)
H430.00970.04410.01680.089*
C440.0745 (4)0.02783 (13)0.0242 (4)0.0669 (9)
H440.18750.02180.01400.080*
C450.0137 (4)0.07677 (11)0.0622 (3)0.0526 (7)
H450.08660.10340.04980.063*
C460.1031 (3)0.18180 (9)0.1194 (3)0.0362 (5)
C470.0810 (3)0.20655 (10)0.2424 (3)0.0396 (5)
C480.0072 (3)0.19553 (10)0.0206 (3)0.0424 (6)
H480.08730.21850.02330.051*
C490.1540 (5)0.2023 (2)0.2892 (4)0.0953 (14)
H49A0.22650.22220.26220.143*
H49B0.21490.17490.35290.143*
H49C0.10840.22330.34110.143*
C500.0990 (4)0.15021 (15)0.1764 (4)0.0656 (9)
H50A0.20770.15730.09990.098*
H50B0.09570.15730.27250.098*
H50C0.07290.11510.17150.098*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0545 (13)0.0591 (13)0.116 (2)0.0199 (11)0.0279 (13)0.0034 (14)
O20.0329 (9)0.1096 (18)0.0546 (11)0.0214 (10)0.0135 (8)0.0147 (12)
N10.0455 (12)0.0397 (11)0.0682 (15)0.0073 (10)0.0186 (11)0.0038 (11)
N20.0361 (11)0.0416 (11)0.0536 (13)0.0007 (9)0.0180 (10)0.0034 (10)
N30.0413 (13)0.0622 (15)0.0681 (16)0.0048 (11)0.0175 (12)0.0114 (13)
N40.0310 (9)0.0552 (12)0.0319 (9)0.0041 (9)0.0151 (8)0.0025 (9)
N50.0324 (10)0.0427 (10)0.0393 (10)0.0059 (8)0.0139 (9)0.0010 (9)
N60.0511 (13)0.0698 (15)0.0336 (10)0.0000 (12)0.0110 (10)0.0079 (11)
C10.070 (2)0.0432 (15)0.085 (2)0.0054 (14)0.0341 (18)0.0158 (15)
C20.0656 (19)0.0390 (14)0.0534 (16)0.0019 (12)0.0180 (14)0.0040 (12)
C30.108 (3)0.079 (3)0.076 (3)0.021 (2)0.035 (2)0.028 (2)
C40.114 (4)0.105 (4)0.101 (4)0.055 (3)0.010 (3)0.028 (3)
C50.079 (3)0.099 (3)0.115 (4)0.029 (3)0.019 (3)0.022 (3)
C60.072 (2)0.095 (3)0.086 (3)0.000 (2)0.033 (2)0.020 (2)
C70.066 (2)0.0657 (19)0.0523 (17)0.0016 (16)0.0167 (15)0.0047 (15)
C80.0367 (13)0.0426 (13)0.0571 (16)0.0019 (10)0.0184 (12)0.0028 (12)
C90.0576 (18)0.0663 (19)0.0562 (17)0.0075 (15)0.0220 (15)0.0102 (15)
C100.0563 (18)0.081 (2)0.0472 (16)0.0087 (17)0.0115 (14)0.0015 (16)
C110.0450 (15)0.0605 (17)0.0595 (18)0.0118 (14)0.0131 (14)0.0101 (15)
C120.0353 (13)0.0443 (13)0.0607 (17)0.0044 (11)0.0186 (12)0.0018 (12)
C130.0296 (11)0.0415 (12)0.0510 (14)0.0006 (10)0.0183 (11)0.0001 (11)
C140.0328 (12)0.0395 (12)0.0543 (15)0.0053 (10)0.0176 (11)0.0002 (11)
C150.0436 (14)0.0525 (15)0.0509 (15)0.0154 (12)0.0156 (12)0.0009 (13)
C160.0627 (19)0.0666 (19)0.0628 (19)0.0213 (16)0.0264 (16)0.0170 (16)
C170.106 (3)0.101 (3)0.068 (2)0.039 (3)0.043 (3)0.030 (2)
C180.106 (4)0.124 (4)0.053 (2)0.048 (3)0.024 (2)0.006 (2)
C190.085 (3)0.102 (3)0.063 (2)0.022 (2)0.011 (2)0.019 (2)
C200.0540 (18)0.082 (2)0.0628 (19)0.0079 (17)0.0154 (15)0.0126 (18)
C210.0332 (13)0.0510 (15)0.0534 (15)0.0041 (11)0.0148 (12)0.0076 (12)
C220.0406 (14)0.0514 (15)0.0709 (19)0.0110 (12)0.0276 (14)0.0037 (14)
C230.0382 (14)0.0561 (17)0.0598 (17)0.0065 (12)0.0188 (13)0.0109 (14)
C240.0465 (17)0.080 (2)0.103 (3)0.0055 (16)0.0344 (18)0.020 (2)
C250.0614 (19)0.0594 (18)0.0644 (19)0.0027 (15)0.0271 (16)0.0008 (15)
C260.0387 (13)0.0580 (15)0.0384 (12)0.0078 (11)0.0215 (11)0.0030 (11)
C270.0376 (12)0.0487 (13)0.0354 (11)0.0012 (10)0.0215 (10)0.0004 (10)
C280.0554 (16)0.0528 (16)0.0432 (14)0.0052 (12)0.0209 (12)0.0048 (12)
C290.0660 (19)0.079 (2)0.0407 (14)0.0038 (17)0.0168 (14)0.0119 (15)
C300.0549 (18)0.085 (2)0.0454 (16)0.0136 (16)0.0146 (14)0.0119 (16)
C310.069 (2)0.0517 (16)0.0672 (19)0.0133 (15)0.0283 (17)0.0141 (15)
C320.0550 (16)0.0454 (14)0.0479 (14)0.0003 (12)0.0189 (13)0.0027 (12)
C330.0278 (10)0.0450 (12)0.0286 (10)0.0033 (9)0.0104 (9)0.0007 (9)
C340.0423 (13)0.0458 (14)0.0370 (12)0.0023 (10)0.0180 (11)0.0049 (10)
C350.0473 (15)0.0484 (14)0.0426 (13)0.0073 (11)0.0168 (12)0.0031 (11)
C360.0342 (13)0.0617 (16)0.0437 (14)0.0055 (11)0.0177 (11)0.0025 (12)
C370.0344 (12)0.0540 (14)0.0371 (12)0.0058 (11)0.0165 (10)0.0002 (11)
C380.0299 (11)0.0410 (12)0.0286 (10)0.0046 (9)0.0086 (9)0.0013 (9)
C390.0341 (11)0.0401 (12)0.0307 (10)0.0051 (9)0.0146 (9)0.0009 (9)
C400.0404 (13)0.0433 (13)0.0334 (11)0.0027 (10)0.0134 (10)0.0000 (10)
C410.0542 (17)0.0476 (15)0.073 (2)0.0075 (14)0.0173 (15)0.0092 (15)
C420.082 (3)0.0462 (17)0.091 (3)0.0060 (17)0.026 (2)0.0073 (17)
C430.091 (3)0.0453 (17)0.068 (2)0.0155 (17)0.018 (2)0.0056 (15)
C440.0591 (19)0.066 (2)0.0635 (19)0.0203 (16)0.0147 (16)0.0001 (16)
C450.0459 (15)0.0496 (15)0.0548 (16)0.0038 (12)0.0147 (13)0.0027 (13)
C460.0301 (11)0.0399 (12)0.0341 (11)0.0030 (9)0.0096 (9)0.0003 (10)
C470.0322 (12)0.0471 (13)0.0392 (12)0.0082 (10)0.0150 (10)0.0020 (11)
C480.0351 (12)0.0457 (13)0.0428 (13)0.0030 (10)0.0135 (10)0.0047 (11)
C490.078 (2)0.147 (4)0.0382 (16)0.010 (3)0.0034 (16)0.020 (2)
C500.075 (2)0.084 (2)0.0486 (16)0.0062 (18)0.0373 (16)0.0038 (16)
Geometric parameters (Å, º) top
O1—C221.231 (3)C21—C231.360 (4)
O2—C471.216 (3)C21—C221.489 (4)
N1—C221.352 (4)C23—H230.9300
N1—C81.425 (3)C24—H24A0.9600
N1—C11.480 (4)C24—H24B0.9600
N2—C141.288 (3)C24—H24C0.9600
N2—C131.403 (3)C25—H25A0.9600
N3—C231.328 (4)C25—H25B0.9600
N3—C241.438 (4)C25—H25C0.9600
N3—C251.458 (5)C26—C271.497 (4)
N4—C471.383 (3)C26—H26A0.9700
N4—C331.432 (3)C26—H26B0.9700
N4—C261.469 (3)C27—C281.383 (4)
N5—C391.286 (3)C27—C321.382 (4)
N5—C381.402 (3)C28—C291.382 (4)
N6—C481.332 (4)C28—H280.9300
N6—C501.444 (4)C29—C301.375 (5)
N6—C491.461 (4)C29—H290.9300
C1—C21.499 (5)C30—C311.369 (5)
C1—H1A0.9700C30—H300.9300
C1—H1B0.9700C31—C321.395 (4)
C2—C71.375 (5)C31—H310.9300
C2—C31.377 (5)C32—H320.9300
C3—C41.376 (8)C33—C341.383 (3)
C3—H30.9300C33—C381.403 (3)
C4—C51.333 (9)C34—C351.385 (4)
C4—H40.9300C34—H340.9300
C5—C61.367 (7)C35—C361.384 (4)
C5—H50.9300C35—H350.9300
C6—C71.379 (5)C36—C371.374 (4)
C6—H60.9300C36—H360.9300
C7—H70.9300C37—C381.391 (3)
C8—C91.386 (4)C37—H370.9300
C8—C131.398 (4)C39—C461.488 (3)
C9—C101.379 (5)C39—C401.490 (4)
C9—H90.9300C40—C451.382 (4)
C10—C111.372 (5)C40—C411.384 (4)
C10—H100.9300C41—C421.391 (5)
C11—C121.371 (4)C41—H410.9300
C11—H110.9300C42—C431.346 (5)
C12—C131.397 (4)C42—H420.9300
C12—H120.9300C43—C441.357 (5)
C14—C211.488 (4)C43—H430.9300
C14—C151.489 (4)C44—C451.385 (4)
C15—C201.375 (5)C44—H440.9300
C15—C161.394 (5)C45—H450.9300
C16—C171.380 (5)C46—C481.360 (3)
C16—H160.9300C46—C471.472 (3)
C17—C181.388 (8)C48—H480.9300
C17—H170.9300C49—H49A0.9600
C18—C191.346 (7)C49—H49B0.9600
C18—H180.9300C49—H49C0.9600
C19—C201.399 (6)C50—H50A0.9600
C19—H190.9300C50—H50B0.9600
C20—H200.9300C50—H50C0.9600
C22—N1—C8121.1 (2)H24B—C24—H24C109.5
C22—N1—C1117.8 (2)N3—C25—H25A109.5
C8—N1—C1118.0 (2)N3—C25—H25B109.5
C14—N2—C13119.6 (2)H25A—C25—H25B109.5
C23—N3—C24123.0 (3)N3—C25—H25C109.5
C23—N3—C25122.9 (3)H25A—C25—H25C109.5
C24—N3—C25113.9 (3)H25B—C25—H25C109.5
C47—N4—C33119.68 (19)N4—C26—C27112.6 (2)
C47—N4—C26118.08 (19)N4—C26—H26A109.1
C33—N4—C26117.39 (19)C27—C26—H26A109.1
C39—N5—C38119.3 (2)N4—C26—H26B109.1
C48—N6—C50123.8 (2)C27—C26—H26B109.1
C48—N6—C49119.7 (3)H26A—C26—H26B107.8
C50—N6—C49116.2 (3)C28—C27—C32118.5 (2)
N1—C1—C2113.3 (2)C28—C27—C26120.2 (2)
N1—C1—H1A108.9C32—C27—C26121.2 (2)
C2—C1—H1A108.9C27—C28—C29121.1 (3)
N1—C1—H1B108.9C27—C28—H28119.5
C2—C1—H1B108.9C29—C28—H28119.5
H1A—C1—H1B107.7C30—C29—C28119.9 (3)
C7—C2—C3116.7 (4)C30—C29—H29120.0
C7—C2—C1122.5 (3)C28—C29—H29120.0
C3—C2—C1120.8 (4)C31—C30—C29119.8 (3)
C4—C3—C2121.6 (5)C31—C30—H30120.1
C4—C3—H3119.2C29—C30—H30120.1
C2—C3—H3119.2C30—C31—C32120.3 (3)
C5—C4—C3120.7 (5)C30—C31—H31119.8
C5—C4—H4119.7C32—C31—H31119.8
C3—C4—H4119.7C27—C32—C31120.3 (3)
C4—C5—C6119.7 (5)C27—C32—H32119.8
C4—C5—H5120.1C31—C32—H32119.8
C6—C5—H5120.1C34—C33—C38119.7 (2)
C5—C6—C7119.9 (5)C34—C33—N4120.1 (2)
C5—C6—H6120.1C38—C33—N4120.2 (2)
C7—C6—H6120.1C33—C34—C35121.1 (2)
C2—C7—C6121.4 (4)C33—C34—H34119.5
C2—C7—H7119.3C35—C34—H34119.5
C6—C7—H7119.3C36—C35—C34119.3 (3)
C9—C8—C13119.3 (2)C36—C35—H35120.4
C9—C8—N1119.7 (3)C34—C35—H35120.4
C13—C8—N1121.0 (3)C37—C36—C35120.1 (2)
C10—C9—C8121.0 (3)C37—C36—H36120.0
C10—C9—H9119.5C35—C36—H36120.0
C8—C9—H9119.5C36—C37—C38121.4 (2)
C11—C10—C9119.9 (3)C36—C37—H37119.3
C11—C10—H10120.1C38—C37—H37119.3
C9—C10—H10120.1C37—C38—N5118.6 (2)
C12—C11—C10120.1 (3)C37—C38—C33118.4 (2)
C12—C11—H11119.9N5—C38—C33122.8 (2)
C10—C11—H11119.9N5—C39—C46124.5 (2)
C11—C12—C13121.0 (3)N5—C39—C40117.5 (2)
C11—C12—H12119.5C46—C39—C40117.8 (2)
C13—C12—H12119.5C45—C40—C41118.1 (3)
C8—C13—C12118.7 (2)C45—C40—C39121.6 (2)
C8—C13—N2123.9 (2)C41—C40—C39120.2 (2)
C12—C13—N2117.3 (2)C40—C41—C42120.0 (3)
N2—C14—C21125.0 (2)C40—C41—H41120.0
N2—C14—C15116.4 (2)C42—C41—H41120.0
C21—C14—C15118.2 (2)C43—C42—C41120.7 (3)
C20—C15—C16118.9 (3)C43—C42—H42119.7
C20—C15—C14121.6 (3)C41—C42—H42119.7
C16—C15—C14119.4 (3)C42—C43—C44120.5 (3)
C17—C16—C15119.9 (4)C42—C43—H43119.7
C17—C16—H16120.0C44—C43—H43119.7
C15—C16—H16120.0C43—C44—C45119.9 (3)
C16—C17—C18120.2 (4)C43—C44—H44120.1
C16—C17—H17119.9C45—C44—H44120.1
C18—C17—H17119.9C40—C45—C44120.8 (3)
C19—C18—C17120.3 (4)C40—C45—H45119.6
C19—C18—H18119.9C44—C45—H45119.6
C17—C18—H18119.9C48—C46—C47115.5 (2)
C18—C19—C20120.1 (4)C48—C46—C39127.9 (2)
C18—C19—H19119.9C47—C46—C39115.57 (19)
C20—C19—H19119.9O2—C47—N4120.7 (2)
C15—C20—C19120.5 (4)O2—C47—C46124.4 (2)
C15—C20—H20119.7N4—C47—C46114.92 (19)
C19—C20—H20119.7N6—C48—C46131.1 (3)
C23—C21—C14131.2 (3)N6—C48—H48114.5
C23—C21—C22113.5 (3)C46—C48—H48114.5
C14—C21—C22114.7 (2)N6—C49—H49A109.5
O1—C22—N1121.2 (3)N6—C49—H49B109.5
O1—C22—C21122.5 (3)H49A—C49—H49B109.5
N1—C22—C21116.2 (2)N6—C49—H49C109.5
N3—C23—C21132.5 (3)H49A—C49—H49C109.5
N3—C23—H23113.7H49B—C49—H49C109.5
C21—C23—H23113.7N6—C50—H50A109.5
N3—C24—H24A109.5N6—C50—H50B109.5
N3—C24—H24B109.5H50A—C50—H50B109.5
H24A—C24—H24B109.5N6—C50—H50C109.5
N3—C24—H24C109.5H50A—C50—H50C109.5
H24A—C24—H24C109.5H50B—C50—H50C109.5
C22—N1—C1—C2147.1 (3)C47—N4—C26—C27148.3 (2)
C8—N1—C1—C252.7 (4)C33—N4—C26—C2756.4 (3)
N1—C1—C2—C740.1 (5)N4—C26—C27—C28138.3 (3)
N1—C1—C2—C3142.6 (4)N4—C26—C27—C3244.3 (3)
C7—C2—C3—C40.8 (6)C32—C27—C28—C292.2 (4)
C1—C2—C3—C4176.6 (4)C26—C27—C28—C29175.3 (3)
C2—C3—C4—C50.3 (8)C27—C28—C29—C300.5 (5)
C3—C4—C5—C60.5 (9)C28—C29—C30—C311.6 (5)
C4—C5—C6—C70.8 (8)C29—C30—C31—C321.8 (5)
C3—C2—C7—C60.5 (5)C28—C27—C32—C312.0 (4)
C1—C2—C7—C6176.8 (3)C26—C27—C32—C31175.5 (3)
C5—C6—C7—C20.2 (6)C30—C31—C32—C270.1 (5)
C22—N1—C8—C9121.1 (3)C47—N4—C33—C34117.1 (2)
C1—N1—C8—C938.4 (4)C26—N4—C33—C3437.8 (3)
C22—N1—C8—C1362.2 (4)C47—N4—C33—C3863.7 (3)
C1—N1—C8—C13138.3 (3)C26—N4—C33—C38141.4 (2)
C13—C8—C9—C100.4 (5)C38—C33—C34—C351.2 (4)
N1—C8—C9—C10176.3 (3)N4—C33—C34—C35179.6 (2)
C8—C9—C10—C110.8 (5)C33—C34—C35—C360.7 (4)
C9—C10—C11—C120.4 (5)C34—C35—C36—C371.2 (4)
C10—C11—C12—C132.8 (4)C35—C36—C37—C382.7 (4)
C9—C8—C13—C122.7 (4)C36—C37—C38—N5178.1 (2)
N1—C8—C13—C12174.0 (2)C36—C37—C38—C332.1 (3)
C9—C8—C13—N2179.2 (3)C39—N5—C38—C37136.3 (2)
N1—C8—C13—N22.6 (4)C39—N5—C38—C3348.0 (3)
C11—C12—C13—C83.9 (4)C34—C33—C38—C370.2 (3)
C11—C12—C13—N2179.3 (3)N4—C33—C38—C37179.0 (2)
C14—N2—C13—C844.4 (4)C34—C33—C38—N5175.9 (2)
C14—N2—C13—C12139.0 (2)N4—C33—C38—N53.3 (3)
C13—N2—C14—C214.4 (4)C38—N5—C39—C462.0 (3)
C13—N2—C14—C15177.8 (2)C38—N5—C39—C40176.3 (2)
N2—C14—C15—C20150.9 (3)N5—C39—C40—C45163.1 (2)
C21—C14—C15—C2022.9 (4)C46—C39—C40—C4511.5 (3)
N2—C14—C15—C1625.1 (4)N5—C39—C40—C4114.6 (4)
C21—C14—C15—C16161.1 (3)C46—C39—C40—C41170.7 (3)
C20—C15—C16—C171.9 (5)C45—C40—C41—C420.2 (5)
C14—C15—C16—C17174.2 (3)C39—C40—C41—C42178.0 (3)
C15—C16—C17—C180.6 (6)C40—C41—C42—C430.6 (6)
C16—C17—C18—C190.9 (7)C41—C42—C43—C440.9 (6)
C17—C18—C19—C201.0 (7)C42—C43—C44—C450.4 (6)
C16—C15—C20—C191.8 (5)C41—C40—C45—C440.7 (4)
C14—C15—C20—C19174.2 (3)C39—C40—C45—C44178.5 (3)
C18—C19—C20—C150.4 (6)C43—C44—C45—C400.4 (5)
N2—C14—C21—C23128.0 (3)N5—C39—C46—C48127.8 (3)
C15—C14—C21—C2358.7 (4)C40—C39—C46—C4857.9 (3)
N2—C14—C21—C2262.0 (4)N5—C39—C46—C4764.5 (3)
C15—C14—C21—C22111.3 (3)C40—C39—C46—C47109.8 (2)
C8—N1—C22—O1153.5 (3)C33—N4—C47—O2144.3 (3)
C1—N1—C22—O16.1 (5)C26—N4—C47—O210.4 (4)
C8—N1—C22—C2129.0 (4)C33—N4—C47—C4637.1 (3)
C1—N1—C22—C21171.4 (3)C26—N4—C47—C46168.2 (2)
C23—C21—C22—O139.9 (4)C48—C46—C47—O230.9 (4)
C14—C21—C22—O1131.8 (3)C39—C46—C47—O2138.3 (3)
C23—C21—C22—N1142.6 (3)C48—C46—C47—N4150.5 (2)
C14—C21—C22—N145.6 (4)C39—C46—C47—N440.2 (3)
C24—N3—C23—C21175.1 (3)C50—N6—C48—C465.8 (5)
C25—N3—C23—C211.0 (5)C49—N6—C48—C46179.4 (3)
C14—C21—C23—N310.9 (6)C47—C46—C48—N6178.1 (3)
C22—C21—C23—N3179.0 (3)C39—C46—C48—N614.2 (5)

Experimental details

Crystal data
Chemical formulaC25H23N3O
Mr381.46
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)8.9733 (3), 26.3103 (7), 9.9312 (3)
β (°) 115.644 (1)
V3)2113.7 (1)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.3 × 0.3 × 0.3
Data collection
DiffractometerBruker APEX2
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
25753, 4959, 4091
Rint0.038
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.118, 1.03
No. of reflections4959
No. of parameters527
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.25, 0.17

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 citationDoubia, M. L., Bouhfid, R., Ahabchane, N. H., Essassi, E. M. & El Ammari, L. (2007a). Acta Cryst. E63, o3305.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationDoubia, M. L., Bouhfid, R., Ahabchane, N. H., Essassi, E. M. & El Ammari, L. (2007b). Acta Cryst. E63, o3306.  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. (2009). publCIF. In preparation.  Google Scholar

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