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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2160.
Published online 2009 August 15. doi:  10.1107/S1600536809031687
PMCID: PMC2969969

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

Abstract

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 [triangle],b [triangle]).

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Object name is e-65-o2160-scheme1.jpg

Experimental

Crystal data

  • C25H23N3O
  • M r = 381.46
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2160-efi1.jpg
  • 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)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 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 [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/S1600536809031687/tk2525sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809031687/tk2525Isup2.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

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

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.

Figures

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.

Crystal data

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

Bruker APEX2 diffractometer4091 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
graphiteθmax = 27.5°, θmin = 2.3°
[var phi] and ω scansh = −11→11
25753 measured reflectionsk = −33→34
4959 independent reflectionsl = −12→12

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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.03w = 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

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

xyzUiso*/Ueq
O10.4567 (3)0.50001 (9)0.2429 (3)0.0798 (8)
O2−0.0517 (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)
N6−0.0202 (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)
H160.72460.3430−0.04270.077*
C170.5928 (6)0.36622 (19)−0.2549 (5)0.0898 (14)
H170.64710.3461−0.29670.108*
C180.4649 (7)0.3979 (2)−0.3453 (5)0.0981 (16)
H180.43480.3993−0.44740.118*
C190.3842 (6)0.4266 (2)−0.2859 (5)0.0903 (14)
H190.29750.4474−0.34730.108*
C200.4305 (4)0.42525 (15)−0.1321 (4)0.0696 (9)
H200.37390.4450−0.09180.084*
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*
H25B0.29380.3222−0.06060.093*
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)
H420.2665−0.03020.11260.092*
C430.0313 (5)−0.01128 (13)0.0430 (4)0.0743 (10)
H43−0.0097−0.04410.01680.089*
C44−0.0745 (4)0.02783 (13)0.0242 (4)0.0669 (9)
H44−0.18750.0218−0.01400.080*
C45−0.0137 (4)0.07677 (11)0.0622 (3)0.0526 (7)
H45−0.08660.10340.04980.063*
C460.1031 (3)0.18180 (9)0.1194 (3)0.0362 (5)
C470.0810 (3)0.20655 (10)0.2424 (3)0.0396 (5)
C48−0.0072 (3)0.19553 (10)−0.0206 (3)0.0424 (6)
H48−0.08730.2185−0.02330.051*
C49−0.1540 (5)0.2023 (2)−0.2892 (4)0.0953 (14)
H49A−0.22650.2222−0.26220.143*
H49B−0.21490.1749−0.35290.143*
H49C−0.10840.2233−0.34110.143*
C500.0990 (4)0.15021 (15)−0.1764 (4)0.0656 (9)
H50A0.20770.1573−0.09990.098*
H50B0.09570.1573−0.27250.098*
H50C0.07290.1151−0.17150.098*

Atomic displacement parameters (Å2)

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, °)

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—C2−147.1 (3)C47—N4—C26—C27148.3 (2)
C8—N1—C1—C252.7 (4)C33—N4—C26—C27−56.4 (3)
N1—C1—C2—C740.1 (5)N4—C26—C27—C28138.3 (3)
N1—C1—C2—C3−142.6 (4)N4—C26—C27—C32−44.3 (3)
C7—C2—C3—C40.8 (6)C32—C27—C28—C29−2.2 (4)
C1—C2—C3—C4−176.6 (4)C26—C27—C28—C29175.3 (3)
C2—C3—C4—C5−0.3 (8)C27—C28—C29—C300.5 (5)
C3—C4—C5—C6−0.5 (9)C28—C29—C30—C311.6 (5)
C4—C5—C6—C70.8 (8)C29—C30—C31—C32−1.8 (5)
C3—C2—C7—C6−0.5 (5)C28—C27—C32—C312.0 (4)
C1—C2—C7—C6176.8 (3)C26—C27—C32—C31−175.5 (3)
C5—C6—C7—C2−0.2 (6)C30—C31—C32—C270.1 (5)
C22—N1—C8—C9−121.1 (3)C47—N4—C33—C34117.1 (2)
C1—N1—C8—C938.4 (4)C26—N4—C33—C34−37.8 (3)
C22—N1—C8—C1362.2 (4)C47—N4—C33—C38−63.7 (3)
C1—N1—C8—C13−138.3 (3)C26—N4—C33—C38141.4 (2)
C13—C8—C9—C100.4 (5)C38—C33—C34—C351.2 (4)
N1—C8—C9—C10−176.3 (3)N4—C33—C34—C35−179.6 (2)
C8—C9—C10—C110.8 (5)C33—C34—C35—C36−0.7 (4)
C9—C10—C11—C120.4 (5)C34—C35—C36—C37−1.2 (4)
C10—C11—C12—C13−2.8 (4)C35—C36—C37—C382.7 (4)
C9—C8—C13—C12−2.7 (4)C36—C37—C38—N5−178.1 (2)
N1—C8—C13—C12174.0 (2)C36—C37—C38—C33−2.1 (3)
C9—C8—C13—N2−179.2 (3)C39—N5—C38—C37−136.3 (2)
N1—C8—C13—N2−2.6 (4)C39—N5—C38—C3348.0 (3)
C11—C12—C13—C83.9 (4)C34—C33—C38—C370.2 (3)
C11—C12—C13—N2−179.3 (3)N4—C33—C38—C37−179.0 (2)
C14—N2—C13—C8−44.4 (4)C34—C33—C38—N5175.9 (2)
C14—N2—C13—C12139.0 (2)N4—C33—C38—N5−3.3 (3)
C13—N2—C14—C214.4 (4)C38—N5—C39—C46−2.0 (3)
C13—N2—C14—C15177.8 (2)C38—N5—C39—C40−176.3 (2)
N2—C14—C15—C20−150.9 (3)N5—C39—C40—C45163.1 (2)
C21—C14—C15—C2022.9 (4)C46—C39—C40—C45−11.5 (3)
N2—C14—C15—C1625.1 (4)N5—C39—C40—C41−14.6 (4)
C21—C14—C15—C16−161.1 (3)C46—C39—C40—C41170.7 (3)
C20—C15—C16—C171.9 (5)C45—C40—C41—C420.2 (5)
C14—C15—C16—C17−174.2 (3)C39—C40—C41—C42178.0 (3)
C15—C16—C17—C18−0.6 (6)C40—C41—C42—C430.6 (6)
C16—C17—C18—C19−0.9 (7)C41—C42—C43—C44−0.9 (6)
C17—C18—C19—C201.0 (7)C42—C43—C44—C450.4 (6)
C16—C15—C20—C19−1.8 (5)C41—C40—C45—C44−0.7 (4)
C14—C15—C20—C19174.2 (3)C39—C40—C45—C44−178.5 (3)
C18—C19—C20—C150.4 (6)C43—C44—C45—C400.4 (5)
N2—C14—C21—C23−128.0 (3)N5—C39—C46—C48127.8 (3)
C15—C14—C21—C2358.7 (4)C40—C39—C46—C48−57.9 (3)
N2—C14—C21—C2262.0 (4)N5—C39—C46—C47−64.5 (3)
C15—C14—C21—C22−111.3 (3)C40—C39—C46—C47109.8 (2)
C8—N1—C22—O1153.5 (3)C33—N4—C47—O2−144.3 (3)
C1—N1—C22—O1−6.1 (5)C26—N4—C47—O210.4 (4)
C8—N1—C22—C21−29.0 (4)C33—N4—C47—C4637.1 (3)
C1—N1—C22—C21171.4 (3)C26—N4—C47—C46−168.2 (2)
C23—C21—C22—O1−39.9 (4)C48—C46—C47—O230.9 (4)
C14—C21—C22—O1131.8 (3)C39—C46—C47—O2−138.3 (3)
C23—C21—C22—N1142.6 (3)C48—C46—C47—N4−150.5 (2)
C14—C21—C22—N1−45.6 (4)C39—C46—C47—N440.2 (3)
C24—N3—C23—C21175.1 (3)C50—N6—C48—C46−5.8 (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—N3−179.0 (3)C39—C46—C48—N6−14.2 (5)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2525).

References

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  • Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Doubia, M. L., Bouhfid, R., Ahabchane, N. H., Essassi, E. M. & El Ammari, L. (2007a). Acta Cryst. E63, o3305.
  • Doubia, M. L., Bouhfid, R., Ahabchane, N. H., Essassi, E. M. & El Ammari, L. (2007b). Acta Cryst. E63, o3306.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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