6-(4-Chloro­phen­yl)-9,9-dimethyl-3,7-dioxo-2,3,4,6,7,8,9,10-octa­hydro-1H-pyrimido[1,2-a]quinoline-5-carbonitrile

Chen, D.-Q.; Li, C.-M.; Tu, S.-J.

doi:10.1107/S1600536807042389

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6-(4-Chlorophenyl)-9,9-dimethyl-3,7-dioxo-2,3,4,6,7,8,9,10-octahydro-1H-pyrimido[1,2-a]quinoline-5-carbonitrile

D.-Q. Chen, C.-M. Li and S.-J. Tu

The title compound, C₂₁H₂₀ClN₃O₂, was synthesized by the reaction of 4-chlorobenzaldehyde and 3-(5,5-dimethyl-3-oxocyclohex-1-enylamino)propanoic acid with malononitrile in ethylene glycol under microwave irradiation. The dihydropyridine ring has a boat conformation. The pyrimidine ring adopts a screw-boat conformation and the cyclohexene ring is in an envelope conformation. In the crystalline state, centrosymmetrically related molecules form dimeric pairs through N—H

N hydrogen bonding. Weak C—H

O hydrogen bonds are also observed.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807042389/ci2454sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807042389/ci2454Isup2.hkl Contains datablock I

CCDC reference: 664190

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.008 Å
R factor = 0.064
wR factor = 0.223
Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         40 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C18
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          8
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl1    ..  N3      ..       3.16 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2     ..  C12     ..       3.01 Ang.

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C3     = ...          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Pyrido[1,2-a]pyrimidine core has been successfully used a motif for the development of biologically interesting molecules, including pirenperone, a tranquilizer (Smith et al., 1995), barmastine, an antiallergic agent (Awouters et al., 1986), an antiulcerative agent (Matsutani et al., 1989), and pemirolast, an antiasthmatic agent (Yanagihara et al., 1988). Pyrimido[1,2-a]quinoline belongs to a class of compounds which are special not only because of their interesting chemical and physical properties, but also due to their immense utility in the pharmaceutical industries. We report here the crystal structure of the title compound, a pyrimido[1,2-a]quinoline derivative.

In the title molecule, the dihydropyridine ring is planar, with a maximum deviation of 0.039 (4) Å for atom C4 (Fig. 1). The pyrimidine ring adopts a screw-boat conformation, with atoms C11 and C10 deviating from the C12/N1/C1/N2 plane by 0.876 (10) and 0.451 (10) Å (Fig. 1). The cyclohexene ring adopts an envelope conformation, with atom C7 deviating by 0.620 (8) Å from the C4/C5/C6/C8/C9 plane. The C1—C4/C9/N1 plane forms dihedral angles 0.5 (4)° and 8.8 (3)°, respectively, with the C12/N1/C1/N2 and C4—C6/C8/C9 planes. The dihedral angle between the dihydropyridine and chlorophenyl rings is 88.6 (2)°.

In the crystalline state, centrosymmetrically related molecules form dimeric pairs through N—H···O hydrogen bonding. In addition, weak C—H···O hydrogen bonds are observed (Table 1).

Related literature top

For general background, see: Awouters et al. (1986); Matsutani & Mizushima (1989); Smith et al. (1995); Yanagihara et al. (1988).

Experimental top

The title compound was prepared by the reaction of 4-chlorobenzaldehyde (0.141 g, 1 mmol), 3-(5,5-dimethyl-3-oxocyclohex-1-enylamino)propanoic acid (0.211 g, 1 mmol) with malononitrile (0.066 g, 1 mmol) in ethylene glycol (2.0 ml) at 393 K under microwave irradiation (maximum power 200 W, initial power 100 W) for 6 min (yield: 0.324 g, 85%; m.p. 539–541 K). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution (95%).

Structure description top

In the crystalline state, centrosymmetrically related molecules form dimeric pairs through N—H···O hydrogen bonding. In addition, weak C—H···O hydrogen bonds are observed (Table 1).

For general background, see: Awouters et al. (1986); Matsutani & Mizushima (1989); Smith et al. (1995); Yanagihara et al. (1988).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.

6-(4-Chlorophenyl)-9,9-dimethyl-3,7-dioxo-2,3,4,6,7,8,9,10-octahydro- 1H-pyrimido[1,2-a]quinoline-5-carbonitrile top

Crystal data top

C₂₁H₂₀ClN₃O₂	F(000) = 800
M_r = 381.85	D_x = 1.341 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 539–541 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.378 (5) Å	Cell parameters from 981 reflections
b = 10.131 (5) Å	θ = 2.8–25.1°
c = 18.143 (9) Å	µ = 0.22 mm⁻¹
β = 97.406 (8)°	T = 298 K
V = 1891.6 (17) Å³	Block, colourless
Z = 4	0.25 × 0.20 × 0.14 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3340 independent reflections
Radiation source: fine-focus sealed tube	1323 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.086
φ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.946, T_max = 0.969	k = −12→11
9514 measured reflections	l = −11→21

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.223	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.035P)² + 2.4335P] where P = (F_o² + 2F_c²)/3
3340 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₁H₂₀ClN₃O₂	V = 1891.6 (17) Å³
M_r = 381.85	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.378 (5) Å	µ = 0.22 mm⁻¹
b = 10.131 (5) Å	T = 298 K
c = 18.143 (9) Å	0.25 × 0.20 × 0.14 mm
β = 97.406 (8)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3340 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1323 reflections with I > 2σ(I)
T_min = 0.946, T_max = 0.969	R_int = 0.086
9514 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.223	H-atom parameters constrained
S = 1.02	Δρ_max = 0.24 e Å⁻³
3340 reflections	Δρ_min = −0.28 e Å⁻³
244 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	0.3493 (2)	0.23717 (18)	1.02619 (13)	0.1007 (8)
N1	0.2832 (4)	0.8830 (4)	0.7610 (2)	0.0424 (11)
N2	0.4295 (4)	1.0056 (5)	0.8419 (3)	0.0555 (13)
H2	0.4812	1.0035	0.8829	0.067*
N3	0.3718 (5)	0.9263 (5)	1.0240 (3)	0.0665 (15)
O1	−0.0473 (4)	0.6160 (4)	0.8355 (2)	0.0685 (13)
O2	0.5347 (6)	1.1839 (5)	0.8066 (3)	0.124 (2)
C1	0.3300 (5)	0.9138 (5)	0.8329 (3)	0.0413 (13)
C2	0.2840 (5)	0.8574 (5)	0.8912 (3)	0.0404 (13)
C3	0.1777 (5)	0.7546 (5)	0.8833 (3)	0.0389 (13)
H3	0.1056	0.7882	0.9079	0.047*
C4	0.1294 (5)	0.7358 (5)	0.8030 (3)	0.0377 (13)
C5	0.0121 (6)	0.6585 (6)	0.7855 (3)	0.0499 (15)
C6	−0.0426 (6)	0.6372 (7)	0.7057 (3)	0.0667 (19)
H6A	−0.0897	0.5543	0.7015	0.080*
H6B	−0.1040	0.7072	0.6904	0.080*
C7	0.0588 (6)	0.6346 (6)	0.6547 (3)	0.0593 (17)
C8	0.1424 (5)	0.7582 (5)	0.6664 (3)	0.0468 (14)
H8A	0.2194	0.7464	0.6419	0.056*
H8B	0.0942	0.8323	0.6429	0.056*
C9	0.1836 (5)	0.7907 (5)	0.7464 (3)	0.0390 (13)
C10	0.4522 (7)	1.0985 (7)	0.7915 (4)	0.073 (2)
C11	0.3695 (6)	1.0920 (6)	0.7190 (4)	0.0691 (19)
H11A	0.4141	1.1322	0.6809	0.083*
H11B	0.2894	1.1402	0.7215	0.083*
C12	0.3395 (6)	0.9501 (6)	0.6998 (3)	0.0619 (18)
H12A	0.2786	0.9456	0.6546	0.074*
H12B	0.4186	0.9052	0.6909	0.074*
C13	0.3332 (6)	0.8955 (5)	0.9641 (4)	0.0499 (15)
C14	0.2223 (5)	0.6256 (5)	0.9202 (3)	0.0382 (13)
C15	0.1652 (5)	0.5741 (5)	0.9779 (3)	0.0491 (15)
H15	0.0986	0.6211	0.9956	0.059*
C16	0.2031 (6)	0.4553 (6)	1.0105 (3)	0.0565 (16)
H16	0.1608	0.4214	1.0485	0.068*
C17	0.3035 (6)	0.3881 (6)	0.9865 (4)	0.0597 (17)
C18	0.3645 (7)	0.4362 (7)	0.9297 (4)	0.078 (2)
H18	0.4328	0.3898	0.9134	0.094*
C19	0.3238 (6)	0.5540 (6)	0.8970 (4)	0.0638 (18)
H19	0.3652	0.5866	0.8583	0.077*
C20	0.1454 (7)	0.5117 (6)	0.6716 (4)	0.085 (2)
H20A	0.2109	0.5099	0.6388	0.128*
H20B	0.0930	0.4336	0.6643	0.128*
H20C	0.1861	0.5152	0.7221	0.128*
C21	−0.0004 (7)	0.6253 (7)	0.5739 (3)	0.080 (2)
H21A	0.0676	0.6237	0.5428	0.120*
H21B	−0.0553	0.7005	0.5614	0.120*
H21C	−0.0510	0.5460	0.5665	0.120*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1119 (16)	0.0658 (12)	0.1244 (19)	0.0265 (11)	0.0145 (14)	0.0319 (12)
N1	0.043 (3)	0.041 (3)	0.045 (3)	−0.012 (2)	0.015 (2)	−0.003 (2)
N2	0.048 (3)	0.054 (3)	0.060 (3)	−0.016 (2)	−0.010 (3)	0.014 (3)
N3	0.066 (4)	0.073 (4)	0.058 (4)	−0.009 (3)	−0.003 (3)	−0.016 (3)
O1	0.060 (3)	0.094 (3)	0.054 (3)	−0.032 (2)	0.017 (2)	0.004 (2)
O2	0.122 (5)	0.110 (4)	0.127 (5)	−0.079 (4)	−0.029 (4)	0.038 (4)
C1	0.039 (3)	0.032 (3)	0.052 (4)	−0.007 (2)	0.003 (3)	0.000 (3)
C2	0.040 (3)	0.036 (3)	0.043 (3)	−0.007 (2)	−0.003 (3)	−0.006 (3)
C3	0.038 (3)	0.038 (3)	0.042 (3)	−0.010 (2)	0.012 (3)	−0.006 (3)
C4	0.037 (3)	0.042 (3)	0.035 (3)	−0.009 (2)	0.004 (3)	−0.008 (3)
C5	0.048 (4)	0.059 (4)	0.043 (4)	−0.010 (3)	0.008 (3)	0.000 (3)
C6	0.060 (4)	0.090 (5)	0.049 (4)	−0.029 (4)	0.005 (4)	−0.002 (4)
C7	0.074 (4)	0.061 (4)	0.043 (4)	−0.027 (3)	0.006 (3)	−0.009 (3)
C8	0.050 (3)	0.050 (3)	0.042 (4)	−0.009 (3)	0.011 (3)	−0.005 (3)
C9	0.037 (3)	0.038 (3)	0.044 (3)	−0.005 (2)	0.010 (3)	−0.003 (3)
C10	0.063 (5)	0.066 (5)	0.086 (5)	−0.020 (4)	−0.003 (4)	0.008 (4)
C11	0.061 (4)	0.069 (5)	0.078 (5)	−0.018 (3)	0.009 (4)	0.012 (4)
C12	0.063 (4)	0.064 (4)	0.061 (4)	−0.014 (3)	0.017 (4)	0.012 (3)
C13	0.053 (4)	0.045 (4)	0.051 (4)	−0.003 (3)	0.006 (3)	0.001 (3)
C14	0.040 (3)	0.038 (3)	0.038 (3)	−0.004 (2)	0.011 (3)	−0.004 (3)
C15	0.060 (4)	0.046 (3)	0.045 (3)	0.003 (3)	0.019 (3)	0.007 (3)
C16	0.057 (4)	0.061 (4)	0.054 (4)	−0.003 (3)	0.018 (3)	0.006 (3)
C17	0.062 (4)	0.049 (4)	0.068 (4)	0.010 (3)	0.005 (4)	0.010 (3)
C18	0.072 (5)	0.079 (5)	0.090 (5)	0.020 (4)	0.034 (4)	0.010 (4)
C19	0.061 (4)	0.064 (4)	0.071 (5)	0.007 (3)	0.028 (4)	0.019 (4)
C20	0.113 (6)	0.062 (5)	0.086 (6)	−0.013 (4)	0.034 (5)	−0.013 (4)
C21	0.108 (6)	0.087 (5)	0.045 (4)	−0.044 (4)	0.006 (4)	−0.015 (4)

Geometric parameters (Å, º) top

Cl1—C17	1.731 (6)	C8—C9	1.496 (7)
N1—C1	1.368 (7)	C8—H8A	0.97
N1—C9	1.394 (6)	C8—H8B	0.97
N1—C12	1.485 (6)	C10—C11	1.476 (9)
N2—C10	1.354 (7)	C11—C12	1.503 (8)
N2—C1	1.384 (6)	C11—H11A	0.97
N2—H2	0.86	C11—H11B	0.97
N3—C13	1.152 (7)	C12—H12A	0.97
O1—C5	1.239 (6)	C12—H12B	0.97
O2—C10	1.224 (7)	C14—C15	1.371 (7)
C1—C2	1.343 (7)	C14—C19	1.388 (7)
C2—C13	1.408 (8)	C15—C16	1.376 (7)
C2—C3	1.511 (6)	C15—H15	0.93
C3—C4	1.492 (7)	C16—C17	1.363 (7)
C3—C14	1.513 (7)	C16—H16	0.93
C3—H3	0.98	C17—C18	1.366 (8)
C4—C9	1.351 (6)	C18—C19	1.376 (8)
C4—C5	1.448 (7)	C18—H18	0.93
C5—C6	1.500 (8)	C19—H19	0.93
C6—C7	1.489 (8)	C20—H20A	0.96
C6—H6A	0.97	C20—H20B	0.96
C6—H6B	0.97	C20—H20C	0.96
C7—C21	1.517 (8)	C21—H21A	0.96
C7—C8	1.523 (7)	C21—H21B	0.96
C7—C20	1.543 (9)	C21—H21C	0.96

C1—N1—C9	119.8 (4)	O2—C10—C11	122.7 (6)
C1—N1—C12	118.9 (4)	N2—C10—C11	116.1 (6)
C9—N1—C12	121.3 (5)	C10—C11—C12	109.1 (6)
C10—N2—C1	125.4 (5)	C10—C11—H11A	109.9
C10—N2—H2	117.3	C12—C11—H11A	109.9
C1—N2—H2	117.3	C10—C11—H11B	109.9
C2—C1—N1	122.4 (5)	C12—C11—H11B	109.9
C2—C1—N2	121.9 (5)	H11A—C11—H11B	108.3
N1—C1—N2	115.7 (5)	N1—C12—C11	110.7 (5)
C1—C2—C13	120.0 (5)	N1—C12—H12A	109.5
C1—C2—C3	123.2 (5)	C11—C12—H12A	109.5
C13—C2—C3	116.8 (5)	N1—C12—H12B	109.5
C4—C3—C2	109.3 (4)	C11—C12—H12B	109.5
C4—C3—C14	111.5 (4)	H12A—C12—H12B	108.1
C2—C3—C14	112.0 (4)	N3—C13—C2	179.1 (7)
C4—C3—H3	107.9	C15—C14—C19	116.9 (5)
C2—C3—H3	107.9	C15—C14—C3	121.9 (5)
C14—C3—H3	107.9	C19—C14—C3	121.2 (5)
C9—C4—C5	118.5 (5)	C14—C15—C16	122.2 (5)
C9—C4—C3	124.7 (4)	C14—C15—H15	118.9
C5—C4—C3	116.7 (5)	C16—C15—H15	118.9
O1—C5—C4	120.8 (5)	C17—C16—C15	119.2 (6)
O1—C5—C6	119.7 (5)	C17—C16—H16	120.4
C4—C5—C6	119.4 (5)	C15—C16—H16	120.4
C7—C6—C5	113.1 (5)	C16—C17—C18	120.7 (6)
C7—C6—H6A	109.0	C16—C17—Cl1	119.2 (5)
C5—C6—H6A	109.0	C18—C17—Cl1	120.0 (5)
C7—C6—H6B	109.0	C17—C18—C19	119.2 (6)
C5—C6—H6B	109.0	C17—C18—H18	120.4
H6A—C6—H6B	107.8	C19—C18—H18	120.4
C6—C7—C21	111.8 (6)	C18—C19—C14	121.7 (6)
C6—C7—C8	109.5 (5)	C18—C19—H19	119.1
C21—C7—C8	109.8 (5)	C14—C19—H19	119.1
C6—C7—C20	109.3 (5)	C7—C20—H20A	109.5
C21—C7—C20	107.1 (5)	C7—C20—H20B	109.5
C8—C7—C20	109.2 (5)	H20A—C20—H20B	109.5
C9—C8—C7	113.7 (4)	C7—C20—H20C	109.5
C9—C8—H8A	108.8	H20A—C20—H20C	109.5
C7—C8—H8A	108.8	H20B—C20—H20C	109.5
C9—C8—H8B	108.8	C7—C21—H21A	109.5
C7—C8—H8B	108.8	C7—C21—H21B	109.5
H8A—C8—H8B	107.7	H21A—C21—H21B	109.5
C4—C9—N1	120.2 (5)	C7—C21—H21C	109.5
C4—C9—C8	123.4 (5)	H21A—C21—H21C	109.5
N1—C9—C8	116.4 (4)	H21B—C21—H21C	109.5
O2—C10—N2	121.2 (7)

C9—N1—C1—C2	0.5 (8)	C3—C4—C9—N1	−7.2 (8)
C12—N1—C1—C2	−180.0 (5)	C5—C4—C9—C8	−10.5 (8)
C9—N1—C1—N2	179.5 (4)	C3—C4—C9—C8	172.9 (5)
C12—N1—C1—N2	−1.0 (7)	C1—N1—C9—C4	2.8 (7)
C10—N2—C1—C2	−156.1 (6)	C12—N1—C9—C4	−176.7 (5)
C10—N2—C1—N1	25.0 (8)	C1—N1—C9—C8	−177.3 (5)
N1—C1—C2—C13	−178.2 (5)	C12—N1—C9—C8	3.2 (7)
N2—C1—C2—C13	2.9 (8)	C7—C8—C9—C4	−14.4 (8)
N1—C1—C2—C3	0.4 (8)	C7—C8—C9—N1	165.7 (5)
N2—C1—C2—C3	−178.5 (5)	C1—N2—C10—O2	172.9 (6)
C1—C2—C3—C4	−3.9 (7)	C1—N2—C10—C11	−5.4 (9)
C13—C2—C3—C4	174.8 (5)	O2—C10—C11—C12	147.4 (7)
C1—C2—C3—C14	120.3 (5)	N2—C10—C11—C12	−34.3 (8)
C13—C2—C3—C14	−61.1 (6)	C1—N1—C12—C11	−37.7 (7)
C2—C3—C4—C9	7.3 (7)	C9—N1—C12—C11	141.8 (5)
C14—C3—C4—C9	−117.1 (5)	C10—C11—C12—N1	53.8 (7)
C2—C3—C4—C5	−169.4 (4)	C4—C3—C14—C15	−118.8 (5)
C14—C3—C4—C5	66.2 (6)	C2—C3—C14—C15	118.4 (5)
C9—C4—C5—O1	−173.6 (5)	C4—C3—C14—C19	61.4 (6)
C3—C4—C5—O1	3.3 (8)	C2—C3—C14—C19	−61.5 (7)
C9—C4—C5—C6	2.4 (8)	C19—C14—C15—C16	−1.8 (8)
C3—C4—C5—C6	179.3 (5)	C3—C14—C15—C16	178.4 (5)
O1—C5—C6—C7	−153.3 (6)	C14—C15—C16—C17	2.1 (9)
C4—C5—C6—C7	30.7 (8)	C15—C16—C17—C18	−1.3 (10)
C5—C6—C7—C21	−174.9 (5)	C15—C16—C17—Cl1	−178.8 (5)
C5—C6—C7—C8	−53.0 (7)	C16—C17—C18—C19	0.2 (11)
C5—C6—C7—C20	66.7 (7)	Cl1—C17—C18—C19	177.6 (5)
C6—C7—C8—C9	45.4 (7)	C17—C18—C19—C14	0.1 (11)
C21—C7—C8—C9	168.5 (5)	C15—C14—C19—C18	0.6 (9)
C20—C7—C8—C9	−74.3 (6)	C3—C14—C19—C18	−179.5 (6)
C5—C4—C9—N1	169.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N3ⁱ	0.86	2.24	3.059 (7)	159
C12—H12B···O2ⁱⁱ	0.97	2.29	3.005 (8)	130
C16—H16···O1ⁱⁱⁱ	0.93	2.57	3.480 (7)	167

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₀ClN₃O₂
M_r	381.85
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.378 (5), 10.131 (5), 18.143 (9)
β (°)	97.406 (8)
V (Å³)	1891.6 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.25 × 0.20 × 0.14

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.946, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	9514, 3340, 1323
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.223, 1.02
No. of reflections	3340
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.28

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N3ⁱ	0.86	2.24	3.059 (7)	159
C12—H12B···O2ⁱⁱ	0.97	2.29	3.005 (8)	130
C16—H16···O1ⁱⁱⁱ	0.93	2.57	3.480 (7)	167

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) −x+1, y−1/2, −z+3/2; (iii) −x, −y+1, −z+2.

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