(Z)-7-Chloro-3-(diméthylaminométhylène)-1-méthyl-5-phényl-1,3-dihydro-2H-[1,4]benzodiazépin-2-one

Benelbaghdadi, R.; Hasnaoui, R.A.; Lavergne, J.P.; Ait Itto, M.; Pierrot, M.

doi:10.1107/S160053680202353X

(Z)-7-Chloro-3-(diméthylaminométhylène)-1-méthyl-5-phényl-1,3-dihydro-2H-[1,4]benzodiazépin-2-one

R. Benelbaghdadi, R. A. Hasnaoui, J. P. Lavergne, M. Ait Itto et M. Pierrot

The title compound, C₁₉H₁₈ClN₃O, contains two molecules in the asymmetric unit, each with a Z conformation.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680202353X/dn6049sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680202353X/dn6049Isup2.hkl Contains datablock I

CCDC reference: 204683

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.046
wR factor = 0.114
Data-to-parameter ratio = 14.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           26.36
         From the CIF: _reflns_number_total               6167
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         6803
         Completeness (_total/calc)             90.65%
          Alert C: < 95% complete


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Comment top

Toutes les benzodiazépines possèdent à des degrés divers des propriétés pharmacologiques identiques: anxiolytiques, sédatives ou hypnotiques, anticonvulsantes et myorelaxantes (Bailly & de Chouly, 1999). Au cours d'une large étude de dérivés benzodiazépiniques, il a été montré que l'introduction d'un hétérocycle à cinq ou six chaînons sur le cycle diazépinique accroît notablement l'activité biologique de la molécule (Raban et al., 1977; Aiello et al., 1978). Développant nos travaux de recherche concernant la synthèse de nouvelles 1,4-benzodiazépines susceptibles de présenter une activité biologique (Benelbaghdadi et al., 1997, 1998, 2000; Essaber et al., 1998; Baouid et al., 1994, 1996), nous décrivons ici le comportement du Diazépam (Valium^R) (Sternbach et al., 1962) en présence du N,N-diméthyl-formamide diméthyl acétal. Cette réaction (Pinto & Fryer, 1993) conduit à un composé de stéréochimie Z ou E dont la structure n'est pas déterminée. L'analyse des spectres de RMN ¹H et ¹³C confirme la présence d'un seul isomère géométrique, cependant elle ne permet pas de trancher entre les deux structures isomères. L'étude cristallographique par diffraction des rayons X a permis de déterminer la stéréochimie exacte du produit obtenu: la structure cristalline du composé montre qu'il s'agit de l'isomère Z (Fig. 1). Le composé cristallize dans le système triclinique, avec 2 molécules indépendantes dans l'unité asymétrique. Ces deux molécules sont parfaitement identiques, comme le montre le tableau des distances et angles de liaison, Table 1 e t leur conformation est comparable. En effet, dans les deux cas, le bicycle benzodiazépine comporte deux fragments plans: (i) le cycle benzo et les 2 atomes voisins du cycle à sept chaînons: N1C5-C11 pour la première molécule et N31C35-C41 pour la deuxième; (ii) le groupement N1C2N4C5 pour la première et N31/C32/C34/C35 pour la deuxième molécule. Ces deux fragments font un angle dièdre de 40.4 (3) e t 47.4 (3)°, respectivement. pour chaque molécule. L'atome C3 (ou C33) porteur du groupement diméthylaminométhylène est à 0.414 (3) Å du plan N1/C2/N4/C5 [C33 à 0.397 (3) Å de N31/C32/N34/C35]. Quelques interactions intermoléculaires sont à noter: (i) entre l'atome de chlore Cl1 et les atomes H18 [2.755 (2) Å] et H16B [2.854 (2) Å]; (ii) entre l'atome d'oxygène O1 et les atomes H15C [2.537 (3) Å] et H9 [2.598 (3) Å]; (iii) enfin, entre l'atome d'oxygène O2 et l'atome H21 [2.570 (3) Å].

Experimental top

Le monocristal est obtenu par recristallization à températute ambiante dans le mélange dichlorométhane–éthanol (1/1).

Computing details top

Data collection: KappaCCD Reference Manual (Nonius, 1998); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. Dessin ORTEPIII (Burnett & Johnson, 1996) de la molécule. Les ellipsoides de vibration des atomes ont une probabilité de 50%..

(I) top

Crystal data top

C₁₉H₁₈ClN₃O	Z = 4
M_r = 339.81	F(000) = 712
Triclinic, P1	D_x = 1.357 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2793 (2) Å	Cell parameters from 22942 reflections
b = 9.4256 (2) Å	θ = 1–26.4°
c = 20.6390 (8) Å	µ = 0.24 mm⁻¹
α = 84.713 (1)°	T = 293 K
β = 80.583 (1)°	Plate, red
γ = 69.210 (1)°	0.4 × 0.3 × 0.1 mm
V = 1663.73 (8) Å³

Data collection top

Nonius KappaCCD diffractometer	5488 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.033
Graphite monochromator	θ_max = 26.4°, θ_min = 2.4°
ϕ scans	h = 0→11
22942 measured reflections	k = −9→10
6167 independent reflections	l = −24→25

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0441P)² + 0.9016P] where P = (F_o² + 2F_c²)/3
6155 reflections	(Δ/σ)_max = 0.001
439 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.49 e Å⁻³

Crystal data top

C₁₉H₁₈ClN₃O	γ = 69.210 (1)°
M_r = 339.81	V = 1663.73 (8) Å³
Triclinic, P1	Z = 4
a = 9.2793 (2) Å	Mo Kα radiation
b = 9.4256 (2) Å	µ = 0.24 mm⁻¹
c = 20.6390 (8) Å	T = 293 K
α = 84.713 (1)°	0.4 × 0.3 × 0.1 mm
β = 80.583 (1)°

Data collection top

Nonius KappaCCD diffractometer	5488 reflections with I > 2σ(I)
22942 measured reflections	R_int = 0.033
6167 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.05	Δρ_max = 0.40 e Å⁻³
6155 reflections	Δρ_min = −0.49 e Å⁻³
439 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Cl1	0.41321 (7)	−0.09461 (7)	0.19881 (3)	0.05967 (17)
Cl2	1.10756 (9)	0.60058 (7)	0.14629 (3)	0.0598 (2)
O1	1.02787 (17)	0.28705 (18)	0.02985 (8)	0.0587 (4)
O2	0.6718 (2)	0.7854 (2)	0.49955 (8)	0.0601 (5)
N1	0.93016 (17)	0.13511 (18)	0.09963 (7)	0.0378 (3)
N4	0.68355 (16)	0.42737 (17)	0.14433 (6)	0.0327 (3)
N14	0.61201 (19)	0.63359 (19)	0.02564 (8)	0.0424 (4)
N31	0.70066 (19)	0.8538 (2)	0.39146 (8)	0.0359 (4)
N34	0.9873 (2)	0.89007 (19)	0.41573 (8)	0.0336 (4)
N44	1.1243 (2)	0.6768 (2)	0.52536 (8)	0.0441 (5)
C2	0.9157 (2)	0.2734 (2)	0.06716 (8)	0.0376 (4)
C3	0.7674 (2)	0.4009 (2)	0.08065 (8)	0.0329 (4)
C5	0.65232 (18)	0.32414 (19)	0.18348 (8)	0.0297 (3)
C6	0.5537 (2)	0.1124 (2)	0.18589 (8)	0.0341 (4)
H6	0.4655	0.1689	0.2159	0.041*
C7	0.5617 (2)	−0.0251 (2)	0.16571 (9)	0.0388 (4)
C8	0.6853 (2)	−0.1081 (2)	0.12173 (9)	0.0436 (4)
H8	0.6883	−0.2036	0.1077	0.052*
C9	0.8031 (2)	−0.0513 (2)	0.09902 (9)	0.0419 (4)
H9	0.8896	−0.1063	0.0679	0.050*
C10	0.8003 (2)	0.0863 (2)	0.11976 (8)	0.0327 (4)
C11	0.67269 (19)	0.17139 (19)	0.16335 (7)	0.0301 (3)
C12	1.0843 (2)	0.0173 (2)	0.08998 (10)	0.0505 (5)
H12A	1.1620	0.0600	0.0941	0.061*
H12B	1.1033	−0.0223	0.0470	0.061*
H12C	1.0889	−0.0632	0.1225	0.061*
C13	0.7389 (2)	0.5109 (2)	0.03122 (8)	0.0350 (4)
H13	0.8274	0.4914	−0.0025	0.042*
C15	0.6097 (3)	0.7347 (3)	−0.03222 (12)	0.0659 (7)
H15A	0.5701	0.8381	−0.0189	0.079*
H15B	0.5441	0.7207	−0.0606	0.079*
H15C	0.7135	0.7121	−0.0552	0.079*
C16	0.4619 (2)	0.6554 (3)	0.06473 (10)	0.0526 (5)
H16A	0.3848	0.6726	0.0362	0.063*
H16B	0.4341	0.7416	0.0916	0.063*
H16C	0.4671	0.5665	0.0923	0.063*
C17	0.57242 (19)	0.3695 (2)	0.25112 (8)	0.0311 (3)
C18	0.4728 (2)	0.5172 (2)	0.26245 (9)	0.0431 (4)
H18	0.4573	0.5918	0.2269	0.052*
C19	0.3948 (3)	0.5591 (3)	0.32470 (10)	0.0521 (5)
H19	0.3256	0.6615	0.3320	0.062*
C20	0.4155 (2)	0.4536 (3)	0.37682 (9)	0.0500 (5)
H20	0.3604	0.4829	0.4198	0.060*
C21	0.5159 (2)	0.3071 (3)	0.36663 (9)	0.0434 (5)
H21	0.5318	0.2338	0.4027	0.052*
C22	0.5941 (2)	0.2645 (2)	0.30426 (8)	0.0358 (4)
H22	0.6639	0.1620	0.2980	0.043*
C32	0.7588 (2)	0.8058 (2)	0.45090 (9)	0.0377 (5)
C33	0.9209 (2)	0.7920 (2)	0.45328 (9)	0.0342 (4)
C35	0.9852 (2)	0.9168 (2)	0.35370 (9)	0.0299 (4)
C36	1.0286 (2)	0.7684 (2)	0.25409 (9)	0.0332 (4)
H36	1.1230	0.7893	0.2397	0.040*
C37	0.9867 (3)	0.6780 (2)	0.21759 (9)	0.0381 (5)
C38	0.8512 (3)	0.6458 (2)	0.23640 (10)	0.0407 (5)
H38	0.8238	0.5833	0.2099	0.049*
C39	0.7576 (2)	0.7053 (2)	0.29368 (10)	0.0377 (5)
H39	0.6626	0.6851	0.3075	0.045*
C40	0.7984 (2)	0.7950 (2)	0.33227 (9)	0.0298 (4)
C41	0.9339 (2)	0.8295 (2)	0.31202 (8)	0.0285 (4)
C42	0.5330 (3)	0.8898 (3)	0.39358 (12)	0.0514 (6)
H42A	0.4778	0.9588	0.4280	0.062*
H42B	0.5024	0.9359	0.3522	0.062*
H42C	0.5090	0.7982	0.4019	0.062*
C43	0.9873 (3)	0.7035 (2)	0.50488 (9)	0.0386 (5)
H43	0.9158	0.6572	0.5280	0.046*
C45	1.1660 (3)	0.5755 (3)	0.58224 (12)	0.0571 (6)
H45A	1.2686	0.5025	0.5717	0.068*
H45B	1.1642	0.6337	0.6184	0.068*
H45C	1.0926	0.5237	0.5942	0.068*
C46	1.2269 (3)	0.7605 (3)	0.50123 (12)	0.0504 (6)
H46A	1.3317	0.6990	0.5071	0.060*
H46B	1.2218	0.7864	0.4554	0.060*
H46C	1.1956	0.8516	0.5252	0.060*
C47	1.0485 (2)	1.0366 (2)	0.32333 (9)	0.0309 (4)
C48	1.1417 (2)	1.0834 (2)	0.35716 (10)	0.0382 (5)
H48	1.1710	1.0334	0.3981	0.046*
C49	1.1931 (3)	1.2007 (3)	0.33217 (12)	0.0469 (5)
H49	1.2580	1.2303	0.3559	0.056*
C50	1.1519 (3)	1.2755 (3)	0.27389 (12)	0.0466 (5)
H50	1.1866	1.3580	0.2570	0.056*
C51	1.0595 (3)	1.2311 (3)	0.23951 (11)	0.0445 (5)
H51	1.0304	1.2831	0.1988	0.053*
C52	1.0089 (2)	1.1123 (2)	0.26384 (10)	0.0350 (4)
H52	0.9459	1.0819	0.2393	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0604 (3)	0.0478 (4)	0.0814 (4)	−0.0323 (3)	−0.0050 (3)	−0.0087 (3)
Cl2	0.0833 (4)	0.0523 (4)	0.0364 (3)	−0.0160 (3)	0.0099 (2)	−0.0142 (2)
O1	0.0441 (8)	0.0563 (10)	0.0585 (9)	−0.0096 (7)	0.0158 (7)	0.0108 (7)
O2	0.0543 (9)	0.0878 (12)	0.0365 (7)	−0.0308 (8)	0.0106 (6)	0.0060 (7)
N1	0.0336 (7)	0.0373 (9)	0.0332 (7)	−0.0045 (6)	0.0006 (6)	0.0038 (6)
N4	0.0376 (7)	0.0326 (8)	0.0270 (7)	−0.0128 (6)	−0.0002 (6)	−0.0019 (5)
N14	0.0456 (9)	0.0388 (10)	0.0415 (8)	−0.0134 (7)	−0.0091 (7)	0.0052 (6)
N31	0.0291 (7)	0.0462 (10)	0.0323 (7)	−0.0133 (6)	0.0004 (6)	−0.0007 (6)
N34	0.0396 (8)	0.0387 (9)	0.0265 (7)	−0.0168 (6)	−0.0051 (6)	0.0005 (5)
N44	0.0554 (10)	0.0461 (10)	0.0346 (8)	−0.0180 (8)	−0.0148 (7)	0.0063 (7)
C2	0.0383 (9)	0.0408 (11)	0.0298 (8)	−0.0120 (7)	0.0007 (7)	0.0013 (7)
C3	0.0372 (9)	0.0342 (10)	0.0267 (8)	−0.0132 (7)	−0.0008 (6)	−0.0011 (6)
C5	0.0314 (8)	0.0300 (9)	0.0278 (8)	−0.0108 (6)	−0.0027 (6)	−0.0027 (6)
C6	0.0380 (9)	0.0312 (10)	0.0335 (8)	−0.0120 (7)	−0.0054 (7)	−0.0033 (6)
C7	0.0443 (10)	0.0344 (11)	0.0413 (10)	−0.0157 (8)	−0.0124 (8)	−0.0002 (7)
C8	0.0574 (12)	0.0307 (11)	0.0439 (10)	−0.0125 (8)	−0.0132 (9)	−0.0068 (7)
C9	0.0505 (11)	0.0335 (11)	0.0327 (9)	−0.0032 (8)	−0.0039 (8)	−0.0065 (7)
C10	0.0373 (9)	0.0311 (10)	0.0249 (7)	−0.0063 (7)	−0.0048 (6)	0.0009 (6)
C11	0.0364 (8)	0.0289 (9)	0.0241 (7)	−0.0099 (7)	−0.0048 (6)	−0.0009 (6)
C12	0.0367 (10)	0.0503 (13)	0.0470 (11)	0.0010 (8)	0.0012 (8)	0.0073 (9)
C13	0.0406 (9)	0.0352 (10)	0.0296 (8)	−0.0151 (7)	−0.0020 (7)	−0.0009 (6)
C15	0.0699 (15)	0.0586 (16)	0.0650 (15)	−0.0186 (12)	−0.0228 (12)	0.0274 (12)
C16	0.0427 (11)	0.0603 (14)	0.0487 (11)	−0.0082 (9)	−0.0086 (9)	−0.0076 (9)
C17	0.0344 (8)	0.0352 (10)	0.0268 (8)	−0.0165 (7)	−0.0003 (6)	−0.0057 (6)
C18	0.0533 (11)	0.0360 (11)	0.0375 (9)	−0.0137 (8)	0.0001 (8)	−0.0068 (7)
C19	0.0555 (12)	0.0484 (13)	0.0465 (11)	−0.0124 (9)	0.0061 (9)	−0.0199 (9)
C20	0.0540 (12)	0.0697 (15)	0.0320 (9)	−0.0307 (11)	0.0082 (8)	−0.0183 (9)
C21	0.0506 (11)	0.0617 (14)	0.0272 (8)	−0.0322 (10)	−0.0028 (7)	−0.0012 (8)
C22	0.0390 (9)	0.0405 (11)	0.0310 (8)	−0.0180 (8)	−0.0033 (7)	−0.0021 (7)
C32	0.0429 (10)	0.0420 (11)	0.0286 (8)	−0.0173 (8)	0.0029 (7)	−0.0012 (7)
C33	0.0431 (9)	0.0391 (10)	0.0248 (8)	−0.0187 (7)	−0.0023 (7)	−0.0010 (6)
C35	0.0281 (8)	0.0335 (10)	0.0282 (8)	−0.0110 (6)	−0.0026 (6)	−0.0005 (6)
C36	0.0343 (9)	0.0365 (10)	0.0277 (8)	−0.0110 (7)	−0.0010 (6)	0.0013 (6)
C37	0.0501 (10)	0.0332 (10)	0.0268 (8)	−0.0091 (8)	−0.0033 (7)	−0.0013 (6)
C38	0.0562 (11)	0.0366 (11)	0.0374 (9)	−0.0187 (8)	−0.0142 (8)	−0.0012 (7)
C39	0.0404 (9)	0.0417 (11)	0.0382 (9)	−0.0200 (8)	−0.0118 (7)	0.0044 (7)
C40	0.0304 (8)	0.0328 (10)	0.0278 (8)	−0.0106 (6)	−0.0049 (6)	0.0029 (6)
C41	0.0310 (8)	0.0299 (9)	0.0257 (7)	−0.0106 (6)	−0.0054 (6)	0.0020 (6)
C42	0.0304 (10)	0.0629 (15)	0.0581 (12)	−0.0144 (9)	0.0017 (8)	−0.0033 (10)
C43	0.0505 (11)	0.0404 (11)	0.0281 (8)	−0.0186 (8)	−0.0030 (7)	−0.0011 (7)
C45	0.0712 (15)	0.0549 (14)	0.0442 (11)	−0.0166 (11)	−0.0205 (10)	0.0112 (9)
C46	0.0541 (12)	0.0562 (14)	0.0487 (11)	−0.0231 (10)	−0.0166 (9)	0.0029 (9)
C47	0.0279 (8)	0.0325 (10)	0.0321 (8)	−0.0108 (6)	−0.0019 (6)	−0.0008 (6)
C48	0.0375 (9)	0.0417 (11)	0.0420 (10)	−0.0174 (8)	−0.0098 (7)	0.0009 (7)
C49	0.0392 (10)	0.0473 (13)	0.0617 (12)	−0.0214 (9)	−0.0092 (9)	−0.0040 (9)
C50	0.0435 (10)	0.0376 (12)	0.0617 (12)	−0.0196 (8)	0.0013 (9)	0.0035 (9)
C51	0.0461 (11)	0.0409 (12)	0.0445 (10)	−0.0143 (8)	−0.0052 (8)	0.0094 (8)
C52	0.0336 (9)	0.0389 (11)	0.0348 (9)	−0.0134 (7)	−0.0062 (7)	0.0030 (7)

Geometric parameters (Å, º) top

Cl1—C7	1.7446 (19)	C17—C22	1.398 (2)
Cl2—C37	1.7403 (18)	C18—C19	1.385 (3)
O1—C2	1.228 (2)	C18—H18	0.9601
O2—C32	1.225 (2)	C19—C20	1.385 (3)
N1—C2	1.382 (2)	C19—H19	0.9599
N1—C10	1.425 (2)	C20—C21	1.377 (3)
N1—C12	1.463 (2)	C20—H20	0.9601
N4—C5	1.289 (2)	C21—C22	1.388 (2)
N4—C3	1.408 (2)	C21—H21	0.9599
N14—C13	1.338 (2)	C22—H22	0.9598
N14—C16	1.447 (3)	C32—C33	1.471 (3)
N14—C15	1.456 (3)	C33—C43	1.376 (2)
N31—C32	1.393 (2)	C35—C41	1.479 (2)
N31—C40	1.425 (2)	C35—C47	1.491 (2)
N31—C42	1.463 (2)	C36—C37	1.377 (3)
N34—C35	1.285 (2)	C36—C41	1.400 (2)
N34—C33	1.399 (2)	C36—H36	0.9600
N44—C43	1.336 (2)	C37—C38	1.381 (3)
N44—C46	1.446 (3)	C38—C39	1.383 (3)
N44—C45	1.456 (2)	C38—H38	0.9600
C2—C3	1.476 (2)	C39—C40	1.391 (2)
C3—C13	1.373 (2)	C39—H39	0.9601
C5—C11	1.474 (2)	C40—C41	1.399 (2)
C5—C17	1.493 (2)	C42—H42A	0.9600
C6—C7	1.372 (3)	C42—H42B	0.9600
C6—C11	1.401 (2)	C42—H42C	0.9600
C6—H6	0.9601	C43—H43	0.9600
C7—C8	1.380 (3)	C45—H45A	0.9600
C8—C9	1.379 (3)	C45—H45B	0.9600
C8—H8	0.9601	C45—H45C	0.9600
C9—C10	1.393 (3)	C46—H46A	0.9600
C9—H9	0.9600	C46—H46B	0.9600
C10—C11	1.402 (2)	C46—H46C	0.9600
C12—H12A	0.9600	C47—C52	1.395 (2)
C12—H12B	0.9600	C47—C48	1.398 (2)
C12—H12C	0.9600	C48—C49	1.378 (3)
C13—H13	0.9601	C48—H48	0.9604
C15—H15A	0.9600	C49—C50	1.380 (3)
C15—H15B	0.9600	C49—H49	0.9599
C15—H15C	0.9600	C50—C51	1.382 (3)
C16—H16A	0.9600	C50—H50	0.9599
C16—H16B	0.9600	C51—C52	1.387 (3)
C16—H16C	0.9600	C51—H51	0.9601
C17—C18	1.386 (3)	C52—H52	0.9601

C2—N1—C10	122.23 (14)	C19—C20—H20	120.0
C2—N1—C12	116.42 (15)	C20—C21—C22	120.27 (18)
C10—N1—C12	117.16 (16)	C20—C21—H21	120.0
C5—N4—C3	124.29 (15)	C22—C21—H21	119.7
C13—N14—C16	124.00 (16)	C21—C22—C17	120.57 (18)
C13—N14—C15	119.21 (17)	C21—C22—H22	119.3
C16—N14—C15	115.09 (17)	C17—C22—H22	120.1
C32—N31—C40	118.68 (14)	O2—C32—N31	119.42 (17)
C32—N31—C42	116.05 (15)	O2—C32—C33	122.71 (17)
C40—N31—C42	117.33 (15)	N31—C32—C33	117.73 (14)
C35—N34—C33	124.31 (15)	C43—C33—N34	121.96 (16)
C43—N44—C46	123.93 (16)	C43—C33—C32	115.31 (16)
C43—N44—C45	119.75 (17)	N34—C33—C32	120.97 (15)
C46—N44—C45	115.34 (17)	N34—C35—C41	123.41 (15)
O1—C2—N1	118.98 (17)	N34—C35—C47	116.45 (15)
O1—C2—C3	122.44 (17)	C41—C35—C47	120.21 (13)
N1—C2—C3	118.55 (15)	C37—C36—C41	120.18 (16)
C13—C3—N4	121.51 (16)	C37—C36—H36	119.8
C13—C3—C2	114.42 (15)	C41—C36—H36	120.1
N4—C3—C2	122.08 (15)	C36—C37—C38	121.55 (16)
N4—C5—C11	124.19 (14)	C36—C37—Cl2	119.39 (14)
N4—C5—C17	117.25 (15)	C38—C37—Cl2	119.06 (15)
C11—C5—C17	118.11 (14)	C37—C38—C39	118.53 (17)
C7—C6—C11	120.85 (16)	C37—C38—H38	120.1
C7—C6—H6	119.5	C39—C38—H38	121.3
C11—C6—H6	119.6	C38—C39—C40	121.19 (17)
C6—C7—C8	121.10 (18)	C38—C39—H39	119.9
C6—C7—Cl1	118.06 (14)	C40—C39—H39	118.9
C8—C7—Cl1	120.82 (15)	C39—C40—C41	119.86 (15)
C7—C8—C9	118.67 (18)	C39—C40—N31	120.11 (15)
C7—C8—H8	120.0	C41—C40—N31	120.03 (15)
C9—C8—H8	121.4	C40—C41—C36	118.66 (16)
C8—C9—C10	121.62 (17)	C40—C41—C35	121.20 (14)
C8—C9—H9	120.2	C36—C41—C35	119.92 (15)
C10—C9—H9	118.1	N31—C42—H42A	109.5
C9—C10—C11	119.32 (17)	N31—C42—H42B	109.5
C9—C10—N1	120.01 (16)	H42A—C42—H42B	109.5
C11—C10—N1	120.57 (16)	N31—C42—H42C	109.5
C10—C11—C6	118.41 (16)	H42A—C42—H42C	109.5
C10—C11—C5	123.34 (15)	H42B—C42—H42C	109.5
C6—C11—C5	118.14 (15)	N44—C43—C33	131.39 (18)
N1—C12—H12A	109.5	N44—C43—H43	120.2
N1—C12—H12B	109.5	C33—C43—H43	108.4
H12A—C12—H12B	109.5	N44—C45—H45A	109.5
N1—C12—H12C	109.5	N44—C45—H45B	109.5
H12A—C12—H12C	109.5	H45A—C45—H45B	109.5
H12B—C12—H12C	109.5	N44—C45—H45C	109.5
N14—C13—C3	129.46 (16)	H45A—C45—H45C	109.5
N14—C13—H13	119.9	H45B—C45—H45C	109.5
C3—C13—H13	110.7	N44—C46—H46A	109.5
N14—C15—H15A	109.5	N44—C46—H46B	109.5
N14—C15—H15B	109.5	H46A—C46—H46B	109.5
H15A—C15—H15B	109.5	N44—C46—H46C	109.5
N14—C15—H15C	109.5	H46A—C46—H46C	109.5
H15A—C15—H15C	109.5	H46B—C46—H46C	109.5
H15B—C15—H15C	109.5	C52—C47—C48	118.10 (16)
N14—C16—H16A	109.5	C52—C47—C35	122.09 (15)
N14—C16—H16B	109.5	C48—C47—C35	119.65 (15)
H16A—C16—H16B	109.5	C49—C48—C47	120.76 (17)
N14—C16—H16C	109.5	C49—C48—H48	119.3
H16A—C16—H16C	109.5	C47—C48—H48	119.9
H16B—C16—H16C	109.5	C48—C49—C50	120.61 (18)
C18—C17—C22	118.41 (16)	C48—C49—H49	119.5
C18—C17—C5	120.47 (15)	C50—C49—H49	119.9
C22—C17—C5	121.12 (16)	C49—C50—C51	119.56 (18)
C19—C18—C17	120.82 (19)	C49—C50—H50	120.4
C19—C18—H18	119.2	C51—C50—H50	120.0
C17—C18—H18	120.0	C50—C51—C52	120.21 (18)
C20—C19—C18	120.3 (2)	C50—C51—H51	119.7
C20—C19—H19	119.5	C52—C51—H51	120.0
C18—C19—H19	120.2	C51—C52—C47	120.75 (17)
C21—C20—C19	119.62 (17)	C51—C52—H52	119.3
C21—C20—H20	120.3	C47—C52—H52	120.0

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈ClN₃O
M_r	339.81
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.2793 (2), 9.4256 (2), 20.6390 (8)
α, β, γ (°)	84.713 (1), 80.583 (1), 69.210 (1)
V (Å³)	1663.73 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.4 × 0.3 × 0.1

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	22942, 6167, 5488
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.114, 1.05
No. of reflections	6155
No. of parameters	439
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.49

Computer programs: KappaCCD Reference Manual (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.

Selected geometric parameters (Å, º) top

Cl1—C7	1.7446 (19)	N31—C42	1.463 (2)
Cl2—C37	1.7403 (18)	N34—C35	1.285 (2)
O1—C2	1.228 (2)	N34—C33	1.399 (2)
O2—C32	1.225 (2)	N44—C43	1.336 (2)
N1—C2	1.382 (2)	N44—C46	1.446 (3)
N1—C10	1.425 (2)	N44—C45	1.456 (2)
N1—C12	1.463 (2)	C2—C3	1.476 (2)
N4—C5	1.289 (2)	C3—C13	1.373 (2)
N4—C3	1.408 (2)	C5—C11	1.474 (2)
N14—C13	1.338 (2)	C10—C11	1.402 (2)
N14—C16	1.447 (3)	C32—C33	1.471 (3)
N14—C15	1.456 (3)	C33—C43	1.376 (2)
N31—C32	1.393 (2)	C35—C41	1.479 (2)
N31—C40	1.425 (2)	C40—C41	1.399 (2)

C2—N1—C10	122.23 (14)	N4—C5—C11	124.19 (14)
C5—N4—C3	124.29 (15)	C9—C10—N1	120.01 (16)
C16—N14—C15	115.09 (17)	C10—C11—C6	118.41 (16)
C32—N31—C40	118.68 (14)	N31—C32—C33	117.73 (14)
C35—N34—C33	124.31 (15)	N34—C33—C32	120.97 (15)
C46—N44—C45	115.34 (17)	N34—C35—C41	123.41 (15)
N1—C2—C3	118.55 (15)	C41—C40—N31	120.03 (15)
N4—C3—C2	122.08 (15)	C40—C41—C35	121.20 (14)

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