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Acta Cryst. (2009). E65, o2160    [ doi:10.1107/S1600536809031687 ]

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

R. M. Zemama, I. Amari, R. Bouhfid, E. M. Essassi and S. W. Ng

Abstract top

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 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 m−3
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 mm−1
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
graphiteθmax = 27.5°, θmin = 2.3°
φ and ω scansh = −11→11
25753 measured reflectionsk = −33→34
4959 independent reflectionsl = −12→12
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 Å−3
1 restraintΔρmin = −0.17 e Å−3
Crystal data top
C25H23N3OV = 2113.7 (1) Å3
Mr = 381.46Z = 4
Monoclinic, P21Mo Kα radiation
a = 8.9733 (3) ŵ = 0.07 mm−1
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		Rint = 0.038
25753 measured reflectionsθmax = 27.5°
4959 independent reflectionsStandard reflections: 0
4091 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.118Δρmax = 0.25 e Å−3
S = 1.03Δρmin = −0.17 e Å−3
4959 reflectionsAbsolute structure: ?
527 parametersFlack parameter: ?
1 restraintRogers parameter: ?
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)
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) 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, °) 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—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)
Acknowledgements top

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

references
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