3-Acetyl-6-chloro-4-phenyl­quinolin-2(1H)-one

Sundar, J.K.; Natarajan, S.; Sarveswari, S.; Vijayakumar, V.; Lakshman, P.L.N.

doi:10.1107/S1600536809054087

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o228

doi:10.1107/S1600536809054087

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3-Acetyl-6-chloro-4-phenylquinolin-2(1H)-one

J. Kalyana Sundar,^a S. Natarajan,^a S. Sarveswari,^b V. Vijayakumar ^b and P. L. Nilantha Lakshman ^c ^*

^aDepartment of Physics, Madurai Kamaraj University, Madurai 625 021, India, ^bOrganic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, India, and ^cDepartment of Food science and Technology, Faculty of Agriculture, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
^*Correspondence e-mail: nilanthalakshman@yahoo.co.uk

(Received 9 December 2009; accepted 15 December 2009; online 24 December 2009)

The title compound, C₁₇H₁₂ClNO₂, crystallizes with two molecules in the asymmetric unit. The main conformational difference between these two molecules is the dihedral angle between the phenyl ring and the quinoline ring system [70.5 (1)° and 65.5 (1) Å]. The crystal packing is stabilized by N—H⋯O hydrogen bonds.

Related literature

For general background, see: Cooper et al. (1992 ); Gaudio et al. (1994 ); Gordeev et al. (1996 ).

Experimental

Crystal data

C₁₇H₁₂ClNO₂
M_r = 297.73
Monoclinic, P 2₁ /n
a = 10.043 (5) Å
b = 18.663 (9) Å
c = 15.537 (7) Å
β = 91.811 (5)°
V = 2911 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 293 K
0.17 × 0.14 × 0.11 mm

Data collection

Nonius MACH-3 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.955, T_max = 0.967
5771 measured reflections
5104 independent reflections
2567 reflections with I > 2σ(I)
R_int = 0.015
2 standard reflections every 60 min
intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.123
S = 1.00
5104 reflections
389 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2⋯O4	0.93 (3)	1.88 (3)	2.807 (3)	171 (3)
N2—H1⋯O3	0.96 (3)	1.84 (3)	2.795 (4)	175 (3)

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054087/bt5138sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809054087/bt5138Isup2.hkl

checkCIF report

Comment top

The molecular structure of the title compound is shown in Fig.1. There are two molecules in the asymmetric unit. The phenyl rings are twisted from the respective quinoline rings by 70.5 (1)° and 65.5 (1) Å.

The two molecules in the asymmetric unit interact through N—H···O bonds (Table 1).

Related literature top

For general background, see: Cooper et al. (1992); Gaudio et al. (1994); Gordeev et al. (1996).

Experimental top

A mixture of 2-amino-5-chlorobenzophenone (2.3 g 0.01 mol) and acetylacetone (1 g, 0.01 mol) with 0.15 ml conc. HCl taken in a beaker was subjected to microwave irradiation for about 6 min. After completion of the reaction (TLC), the reaction mixture was washed with saturated solution NaHCO₃ (10 ml) and then dried. After that it was washed with petroleum ether and recrystallized with ethanol. m.p.224–226 °C.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.

3-Acetyl-6-chloro-4-phenylquinolin-2(1H)-one top

Crystal data top

C₁₇H₁₂ClNO₂	F(000) = 1232
M_r = 297.73	D_x = 1.359 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71069 Å
a = 10.043 (5) Å	Cell parameters from 25 reflections
b = 18.663 (9) Å	θ = 2–25°
c = 15.537 (7) Å	µ = 0.27 mm⁻¹
β = 91.811 (5)°	T = 293 K
V = 2911 (2) Å³	Block, colourless
Z = 8	0.17 × 0.14 × 0.11 mm

Data collection top

Nonius MACH-3 diffractometer	2567 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.015
Graphite monochromator	θ_max = 25.0°, θ_min = 2.2°
ω–2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = −1→22
T_min = 0.955, T_max = 0.967	l = −18→18
5771 measured reflections	2 standard reflections every 60 min
5104 independent reflections	intensity decay: none

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0478P)² + 0.722P] where P = (F_o² + 2F_c²)/3
5104 reflections	(Δ/σ)_max < 0.001
389 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₇H₁₂ClNO₂	V = 2911 (2) Å³
M_r = 297.73	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.043 (5) Å	µ = 0.27 mm⁻¹
b = 18.663 (9) Å	T = 293 K
c = 15.537 (7) Å	0.17 × 0.14 × 0.11 mm
β = 91.811 (5)°

Data collection top

Nonius MACH-3 diffractometer	2567 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.015
T_min = 0.955, T_max = 0.967	2 standard reflections every 60 min
5771 measured reflections	intensity decay: none
5104 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.22 e Å⁻³
5104 reflections	Δρ_min = −0.18 e Å⁻³
389 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
H1	0.316 (3)	0.4766 (17)	0.3548 (19)	0.084 (10)*
H2	0.433 (3)	0.4103 (15)	0.4718 (18)	0.073 (9)*
C2	0.2436 (3)	0.38557 (15)	0.48154 (18)	0.0546 (7)
C3	0.1547 (3)	0.34166 (14)	0.53187 (16)	0.0490 (7)
C4	0.2019 (3)	0.29962 (14)	0.59716 (16)	0.0478 (7)
C5	0.3441 (3)	0.29580 (14)	0.61547 (17)	0.0485 (7)
C6	0.4299 (3)	0.33733 (14)	0.56559 (17)	0.0503 (7)
C7	0.5675 (3)	0.33402 (16)	0.5801 (2)	0.0637 (8)
H7	0.6233	0.3615	0.5466	0.076*
C8	0.6211 (3)	0.29074 (18)	0.6431 (2)	0.0702 (9)
H8	0.7129	0.2888	0.6528	0.084*
C9	0.5373 (3)	0.24975 (17)	0.69226 (19)	0.0657 (9)
C10	0.4021 (3)	0.25169 (16)	0.67917 (18)	0.0583 (8)
H10	0.3482	0.2234	0.7129	0.070*
C11	0.1106 (2)	0.25720 (14)	0.65164 (17)	0.0474 (7)
C12	0.0419 (3)	0.19869 (16)	0.6198 (2)	0.0678 (9)
H12	0.0509	0.1850	0.5628	0.081*
C13	−0.0410 (3)	0.16005 (18)	0.6726 (3)	0.0794 (10)
H13	−0.0875	0.1206	0.6507	0.095*
C14	−0.0545 (3)	0.17966 (19)	0.7567 (2)	0.0748 (10)
H14	−0.1102	0.1537	0.7919	0.090*
C15	0.0141 (3)	0.23736 (19)	0.7888 (2)	0.0763 (10)
H15	0.0056	0.2505	0.8461	0.092*
C16	0.0953 (3)	0.27593 (16)	0.7369 (2)	0.0666 (9)
H16	0.1409	0.3154	0.7593	0.080*
C17	0.0084 (3)	0.34993 (18)	0.51066 (19)	0.0617 (8)
C18	−0.0616 (4)	0.4092 (2)	0.5505 (3)	0.1200 (16)
H18A	−0.1458	0.4165	0.5209	0.180*
H18B	−0.0090	0.4520	0.5471	0.180*
H18C	−0.0761	0.3981	0.6098	0.180*
O3	0.20241 (19)	0.42606 (11)	0.42292 (13)	0.0695 (6)
C22	0.5109 (3)	0.48911 (15)	0.33411 (18)	0.0540 (7)
C23	0.6000 (3)	0.51645 (14)	0.26931 (17)	0.0509 (7)
C24	0.5525 (3)	0.55259 (14)	0.19914 (17)	0.0496 (7)
C25	0.4099 (3)	0.56463 (15)	0.18733 (17)	0.0516 (7)
C26	0.3239 (3)	0.53486 (14)	0.24734 (18)	0.0510 (7)
C27	0.1863 (3)	0.54169 (16)	0.2368 (2)	0.0623 (8)
H27	0.1307	0.5204	0.2761	0.075*
C28	0.1325 (3)	0.57966 (17)	0.1688 (2)	0.0680 (9)
H28	0.0406	0.5846	0.1618	0.082*
C29	0.2171 (3)	0.61076 (17)	0.11031 (19)	0.0671 (9)
C30	0.3526 (3)	0.60242 (17)	0.11801 (19)	0.0645 (8)
H30	0.4068	0.6221	0.0767	0.077*
C31	0.6424 (3)	0.57753 (16)	0.12980 (17)	0.0527 (7)
C32	0.7112 (3)	0.52777 (19)	0.0823 (2)	0.0745 (9)
H32	0.7018	0.4792	0.0938	0.089*
C33	0.7940 (4)	0.5498 (2)	0.0177 (2)	0.0924 (12)
H33	0.8403	0.5160	−0.0136	0.111*
C34	0.8076 (3)	0.6212 (3)	−0.0001 (2)	0.0867 (12)
H34	0.8627	0.6358	−0.0437	0.104*
C35	0.7409 (3)	0.6706 (2)	0.0460 (2)	0.0774 (10)
H35	0.7510	0.7191	0.0342	0.093*
C36	0.6580 (3)	0.64907 (17)	0.11062 (19)	0.0648 (8)
H36	0.6121	0.6833	0.1415	0.078*
C37	0.7460 (3)	0.50148 (17)	0.28466 (17)	0.0565 (8)
C38	0.7913 (3)	0.42529 (17)	0.2902 (3)	0.0913 (11)
H38A	0.7661	0.4008	0.2379	0.137*
H38B	0.7505	0.4023	0.3379	0.137*
H38C	0.8864	0.4239	0.2983	0.137*
O4	0.5515 (2)	0.45877 (11)	0.40079 (13)	0.0677 (6)
N1	0.3760 (2)	0.38020 (13)	0.50155 (15)	0.0564 (6)
N2	0.3779 (3)	0.49874 (13)	0.31750 (15)	0.0553 (6)
O1	−0.0477 (3)	0.30921 (15)	0.46303 (19)	0.1134 (9)
O2	0.8246 (2)	0.55021 (12)	0.28979 (15)	0.0813 (7)
Cl1	0.60397 (9)	0.19417 (7)	0.77191 (7)	0.1139 (4)
Cl2	0.15123 (9)	0.65908 (6)	0.02361 (6)	0.0999 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.060 (2)	0.0565 (19)	0.0479 (17)	−0.0054 (15)	0.0101 (15)	0.0036 (15)
C3	0.0520 (16)	0.0511 (17)	0.0443 (15)	−0.0056 (14)	0.0084 (13)	0.0003 (14)
C4	0.0523 (17)	0.0437 (16)	0.0479 (16)	−0.0037 (13)	0.0105 (13)	−0.0030 (13)
C5	0.0505 (17)	0.0454 (16)	0.0501 (16)	−0.0034 (14)	0.0107 (13)	−0.0038 (14)
C6	0.0542 (18)	0.0470 (16)	0.0501 (17)	−0.0045 (14)	0.0089 (14)	−0.0023 (14)
C7	0.0529 (19)	0.069 (2)	0.070 (2)	−0.0135 (16)	0.0154 (16)	0.0013 (17)
C8	0.0497 (18)	0.085 (2)	0.076 (2)	−0.0036 (18)	0.0037 (16)	0.007 (2)
C9	0.0530 (19)	0.076 (2)	0.069 (2)	0.0034 (16)	0.0095 (16)	0.0154 (17)
C10	0.0526 (18)	0.0593 (19)	0.0640 (19)	−0.0007 (15)	0.0158 (15)	0.0086 (16)
C11	0.0426 (15)	0.0479 (17)	0.0521 (17)	0.0028 (13)	0.0079 (13)	0.0070 (14)
C12	0.068 (2)	0.066 (2)	0.069 (2)	−0.0150 (18)	−0.0003 (16)	0.0054 (17)
C13	0.062 (2)	0.071 (2)	0.104 (3)	−0.0253 (18)	−0.008 (2)	0.023 (2)
C14	0.0497 (19)	0.079 (3)	0.096 (3)	0.0066 (18)	0.0165 (18)	0.040 (2)
C15	0.086 (2)	0.070 (2)	0.075 (2)	0.005 (2)	0.031 (2)	0.0133 (19)
C16	0.075 (2)	0.0580 (19)	0.069 (2)	−0.0048 (16)	0.0233 (17)	0.0036 (16)
C17	0.061 (2)	0.070 (2)	0.0540 (19)	−0.0131 (18)	0.0008 (16)	0.0155 (17)
C18	0.062 (2)	0.148 (4)	0.150 (4)	0.021 (2)	0.007 (2)	−0.056 (3)
O3	0.0667 (13)	0.0785 (15)	0.0636 (13)	−0.0070 (11)	0.0064 (11)	0.0250 (12)
C22	0.065 (2)	0.0456 (17)	0.0517 (19)	−0.0083 (15)	0.0096 (15)	0.0025 (14)
C23	0.0564 (18)	0.0438 (16)	0.0529 (17)	−0.0061 (14)	0.0064 (14)	0.0009 (14)
C24	0.0512 (17)	0.0461 (17)	0.0520 (17)	−0.0047 (13)	0.0084 (14)	−0.0015 (14)
C25	0.0525 (17)	0.0527 (17)	0.0503 (17)	−0.0030 (14)	0.0112 (14)	0.0027 (14)
C26	0.0569 (18)	0.0448 (16)	0.0520 (17)	−0.0033 (14)	0.0137 (14)	0.0016 (14)
C27	0.0556 (19)	0.066 (2)	0.066 (2)	−0.0048 (16)	0.0230 (16)	0.0043 (17)
C28	0.0487 (18)	0.078 (2)	0.078 (2)	0.0020 (17)	0.0134 (17)	0.0088 (19)
C29	0.055 (2)	0.078 (2)	0.069 (2)	0.0055 (16)	0.0119 (16)	0.0189 (17)
C30	0.0538 (19)	0.081 (2)	0.0591 (19)	−0.0009 (16)	0.0145 (15)	0.0191 (17)
C31	0.0457 (16)	0.0646 (19)	0.0481 (16)	−0.0035 (15)	0.0068 (13)	0.0030 (15)
C32	0.071 (2)	0.077 (2)	0.076 (2)	−0.0058 (18)	0.0191 (19)	−0.0045 (19)
C33	0.083 (3)	0.122 (3)	0.074 (2)	0.002 (2)	0.034 (2)	−0.012 (2)
C34	0.057 (2)	0.139 (4)	0.064 (2)	−0.012 (2)	0.0140 (17)	0.021 (2)
C35	0.061 (2)	0.093 (3)	0.079 (2)	−0.0124 (19)	0.0078 (18)	0.029 (2)
C36	0.0572 (19)	0.070 (2)	0.068 (2)	−0.0015 (16)	0.0098 (16)	0.0126 (17)
C37	0.0568 (19)	0.058 (2)	0.0544 (18)	−0.0079 (16)	0.0008 (14)	0.0053 (15)
C38	0.072 (2)	0.064 (2)	0.138 (3)	0.0064 (19)	−0.001 (2)	0.011 (2)
O4	0.0733 (14)	0.0715 (14)	0.0584 (13)	−0.0113 (11)	0.0020 (11)	0.0184 (11)
N1	0.0574 (16)	0.0558 (16)	0.0566 (16)	−0.0119 (13)	0.0096 (13)	0.0084 (13)
N2	0.0586 (17)	0.0535 (15)	0.0546 (15)	−0.0056 (13)	0.0168 (13)	0.0062 (12)
O1	0.099 (2)	0.107 (2)	0.130 (2)	−0.0089 (17)	−0.0444 (17)	−0.0113 (18)
O2	0.0640 (14)	0.0715 (15)	0.1075 (18)	−0.0165 (12)	−0.0092 (13)	0.0025 (13)
Cl1	0.0605 (6)	0.1552 (10)	0.1260 (9)	0.0132 (6)	0.0028 (5)	0.0715 (8)
Cl2	0.0609 (5)	0.1354 (9)	0.1034 (7)	0.0066 (5)	0.0018 (5)	0.0541 (7)

Geometric parameters (Å, º) top

C2—O3	1.244 (3)	C22—N2	1.365 (4)
C2—N1	1.360 (4)	C22—C23	1.460 (4)
C2—C3	1.457 (4)	C23—C24	1.356 (4)
C3—C4	1.356 (3)	C23—C37	1.504 (4)
C3—C17	1.504 (4)	C24—C25	1.455 (4)
C4—C5	1.449 (4)	C24—C31	1.501 (4)
C4—C11	1.494 (3)	C25—C30	1.397 (4)
C5—C10	1.400 (4)	C25—C26	1.405 (4)
C5—C6	1.410 (4)	C26—N2	1.378 (3)
C6—N1	1.374 (3)	C26—C27	1.393 (4)
C6—C7	1.395 (4)	C27—C28	1.369 (4)
C7—C8	1.366 (4)	C27—H27	0.9300
C7—H7	0.9300	C28—C29	1.390 (4)
C8—C9	1.385 (4)	C28—H28	0.9300
C8—H8	0.9300	C29—C30	1.371 (4)
C9—C10	1.367 (4)	C29—Cl2	1.735 (3)
C9—Cl1	1.733 (3)	C30—H30	0.9300
C10—H10	0.9300	C31—C36	1.378 (4)
C11—C12	1.375 (4)	C31—C32	1.385 (4)
C11—C16	1.383 (4)	C32—C33	1.385 (4)
C12—C13	1.389 (4)	C32—H32	0.9300
C12—H12	0.9300	C33—C34	1.368 (5)
C13—C14	1.368 (5)	C33—H33	0.9300
C13—H13	0.9300	C34—C35	1.358 (5)
C14—C15	1.364 (4)	C34—H34	0.9300
C14—H14	0.9300	C35—C36	1.384 (4)
C15—C16	1.370 (4)	C35—H35	0.9300
C15—H15	0.9300	C36—H36	0.9300
C16—H16	0.9300	C37—O2	1.206 (3)
C17—O1	1.190 (3)	C37—C38	1.495 (4)
C17—C18	1.459 (5)	C38—H38A	0.9600
C18—H18A	0.9600	C38—H38B	0.9600
C18—H18B	0.9600	C38—H38C	0.9600
C18—H18C	0.9600	N1—H2	0.93 (3)
C22—O4	1.238 (3)	N2—H1	0.96 (3)

O3—C2—N1	120.8 (3)	C24—C23—C22	121.4 (3)
O3—C2—C3	122.6 (3)	C24—C23—C37	122.5 (2)
N1—C2—C3	116.5 (3)	C22—C23—C37	116.2 (3)
C4—C3—C2	121.4 (3)	C23—C24—C25	119.9 (2)
C4—C3—C17	122.6 (2)	C23—C24—C31	121.8 (2)
C2—C3—C17	115.8 (2)	C25—C24—C31	118.3 (2)
C3—C4—C5	119.6 (2)	C30—C25—C26	117.7 (3)
C3—C4—C11	121.6 (2)	C30—C25—C24	123.7 (2)
C5—C4—C11	118.8 (2)	C26—C25—C24	118.6 (3)
C10—C5—C6	117.6 (3)	N2—C26—C27	120.1 (2)
C10—C5—C4	123.6 (2)	N2—C26—C25	118.9 (3)
C6—C5—C4	118.7 (3)	C27—C26—C25	120.9 (3)
N1—C6—C7	120.6 (3)	C28—C27—C26	120.3 (3)
N1—C6—C5	119.0 (3)	C28—C27—H27	119.9
C7—C6—C5	120.5 (3)	C26—C27—H27	119.9
C8—C7—C6	120.5 (3)	C27—C28—C29	119.1 (3)
C8—C7—H7	119.8	C27—C28—H28	120.5
C6—C7—H7	119.8	C29—C28—H28	120.5
C7—C8—C9	119.3 (3)	C30—C29—C28	121.4 (3)
C7—C8—H8	120.3	C30—C29—Cl2	118.7 (2)
C9—C8—H8	120.3	C28—C29—Cl2	119.9 (2)
C10—C9—C8	121.4 (3)	C29—C30—C25	120.6 (3)
C10—C9—Cl1	118.8 (2)	C29—C30—H30	119.7
C8—C9—Cl1	119.8 (2)	C25—C30—H30	119.7
C9—C10—C5	120.7 (3)	C36—C31—C32	118.2 (3)
C9—C10—H10	119.7	C36—C31—C24	122.0 (3)
C5—C10—H10	119.7	C32—C31—C24	119.8 (3)
C12—C11—C16	118.4 (3)	C31—C32—C33	120.5 (3)
C12—C11—C4	121.8 (3)	C31—C32—H32	119.7
C16—C11—C4	119.8 (2)	C33—C32—H32	119.7
C11—C12—C13	120.2 (3)	C34—C33—C32	120.1 (3)
C11—C12—H12	119.9	C34—C33—H33	120.0
C13—C12—H12	119.9	C32—C33—H33	120.0
C14—C13—C12	120.3 (3)	C35—C34—C33	120.1 (3)
C14—C13—H13	119.8	C35—C34—H34	120.0
C12—C13—H13	119.8	C33—C34—H34	120.0
C15—C14—C13	119.8 (3)	C34—C35—C36	120.2 (3)
C15—C14—H14	120.1	C34—C35—H35	119.9
C13—C14—H14	120.1	C36—C35—H35	119.9
C14—C15—C16	120.2 (3)	C31—C36—C35	120.9 (3)
C14—C15—H15	119.9	C31—C36—H36	119.6
C16—C15—H15	119.9	C35—C36—H36	119.6
C15—C16—C11	121.2 (3)	O2—C37—C38	121.1 (3)
C15—C16—H16	119.4	O2—C37—C23	120.2 (3)
C11—C16—H16	119.4	C38—C37—C23	118.7 (3)
O1—C17—C18	121.5 (3)	C37—C38—H38A	109.5
O1—C17—C3	120.7 (3)	C37—C38—H38B	109.5
C18—C17—C3	117.7 (3)	H38A—C38—H38B	109.5
C17—C18—H18A	109.5	C37—C38—H38C	109.5
C17—C18—H18B	109.5	H38A—C38—H38C	109.5
H18A—C18—H18B	109.5	H38B—C38—H38C	109.5
C17—C18—H18C	109.5	C2—N1—C6	124.6 (2)
H18A—C18—H18C	109.5	C2—N1—H2	116.8 (18)
H18B—C18—H18C	109.5	C6—N1—H2	118.4 (18)
O4—C22—N2	120.9 (2)	C22—N2—C26	124.9 (2)
O4—C22—C23	123.0 (3)	C22—N2—H1	118.6 (18)
N2—C22—C23	116.2 (3)	C26—N2—H1	116.4 (18)

O3—C2—C3—C4	−178.0 (3)	C22—C23—C24—C25	−0.1 (4)
N1—C2—C3—C4	2.2 (4)	C37—C23—C24—C25	179.2 (3)
O3—C2—C3—C17	−1.9 (4)	C22—C23—C24—C31	−176.7 (2)
N1—C2—C3—C17	178.2 (3)	C37—C23—C24—C31	2.6 (4)
C2—C3—C4—C5	−2.5 (4)	C23—C24—C25—C30	178.7 (3)
C17—C3—C4—C5	−178.2 (3)	C31—C24—C25—C30	−4.6 (4)
C2—C3—C4—C11	177.0 (2)	C23—C24—C25—C26	−3.3 (4)
C17—C3—C4—C11	1.3 (4)	C31—C24—C25—C26	173.4 (2)
C3—C4—C5—C10	−177.3 (3)	C30—C25—C26—N2	−178.5 (2)
C11—C4—C5—C10	3.2 (4)	C24—C25—C26—N2	3.4 (4)
C3—C4—C5—C6	1.3 (4)	C30—C25—C26—C27	1.3 (4)
C11—C4—C5—C6	−178.3 (2)	C24—C25—C26—C27	−176.8 (3)
C10—C5—C6—N1	178.9 (2)	N2—C26—C27—C28	177.7 (3)
C4—C5—C6—N1	0.2 (4)	C25—C26—C27—C28	−2.0 (4)
C10—C5—C6—C7	−0.1 (4)	C26—C27—C28—C29	0.4 (5)
C4—C5—C6—C7	−178.7 (2)	C27—C28—C29—C30	1.9 (5)
N1—C6—C7—C8	−179.2 (3)	C27—C28—C29—Cl2	180.0 (2)
C5—C6—C7—C8	−0.3 (4)	C28—C29—C30—C25	−2.7 (5)
C6—C7—C8—C9	0.4 (5)	Cl2—C29—C30—C25	179.3 (2)
C7—C8—C9—C10	0.0 (5)	C26—C25—C30—C29	1.0 (4)
C7—C8—C9—Cl1	179.6 (2)	C24—C25—C30—C29	179.0 (3)
C8—C9—C10—C5	−0.3 (5)	C23—C24—C31—C36	−117.9 (3)
Cl1—C9—C10—C5	−180.0 (2)	C25—C24—C31—C36	65.5 (4)
C6—C5—C10—C9	0.4 (4)	C23—C24—C31—C32	63.0 (4)
C4—C5—C10—C9	178.9 (3)	C25—C24—C31—C32	−113.7 (3)
C3—C4—C11—C12	70.2 (4)	C36—C31—C32—C33	0.4 (5)
C5—C4—C11—C12	−110.3 (3)	C24—C31—C32—C33	179.6 (3)
C3—C4—C11—C16	−110.8 (3)	C31—C32—C33—C34	−0.5 (5)
C5—C4—C11—C16	68.7 (3)	C32—C33—C34—C35	0.5 (6)
C16—C11—C12—C13	0.3 (4)	C33—C34—C35—C36	−0.6 (5)
C4—C11—C12—C13	179.3 (3)	C32—C31—C36—C35	−0.5 (4)
C11—C12—C13—C14	−0.3 (5)	C24—C31—C36—C35	−179.6 (3)
C12—C13—C14—C15	−0.2 (5)	C34—C35—C36—C31	0.5 (5)
C13—C14—C15—C16	0.6 (5)	C24—C23—C37—O2	58.7 (4)
C14—C15—C16—C11	−0.6 (5)	C22—C23—C37—O2	−122.0 (3)
C12—C11—C16—C15	0.2 (4)	C24—C23—C37—C38	−119.2 (3)
C4—C11—C16—C15	−178.9 (3)	C22—C23—C37—C38	60.2 (4)
C4—C3—C17—O1	−87.4 (4)	O3—C2—N1—C6	179.5 (3)
C2—C3—C17—O1	96.6 (4)	C3—C2—N1—C6	−0.7 (4)
C4—C3—C17—C18	92.4 (4)	C7—C6—N1—C2	178.4 (3)
C2—C3—C17—C18	−83.5 (4)	C5—C6—N1—C2	−0.5 (4)
O4—C22—C23—C24	−176.6 (3)	O4—C22—N2—C26	176.7 (3)
N2—C22—C23—C24	3.4 (4)	C23—C22—N2—C26	−3.3 (4)
O4—C22—C23—C37	4.0 (4)	C27—C26—N2—C22	−179.8 (3)
N2—C22—C23—C37	−176.0 (2)	C25—C26—N2—C22	0.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2···O4	0.93 (3)	1.88 (3)	2.807 (3)	171 (3)
N2—H1···O3	0.96 (3)	1.84 (3)	2.795 (4)	175 (3)

Experimental details

Crystal data
Chemical formula	C₁₇H₁₂ClNO₂
M_r	297.73
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.043 (5), 18.663 (9), 15.537 (7)
β (°)	91.811 (5)
V (Å³)	2911 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.17 × 0.14 × 0.11

Data collection
Diffractometer	Nonius MACH-3 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.955, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	5771, 5104, 2567
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.123, 1.00
No. of reflections	5104
No. of parameters	389
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.18

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2···O4	0.93 (3)	1.88 (3)	2.807 (3)	171 (3)
N2—H1···O3	0.96 (3)	1.84 (3)	2.795 (4)	175 (3)

Acknowledgements

SN thanks the DST for the FIST programme and VV thanks the DST-India for funding through the Young Scientist-Fast Track Proposal.

References

Cooper, K. M., Fray, J. M., Parry, J., Richardson, K. & Steele, J. (1992). J. Med. Chem. 35, 3115–3129. CrossRef PubMed CAS Web of Science Google Scholar
Enraf–Nonius (1994). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
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Harms, K. & Wocadlo, S. (1996). XCAD4. University of Marburg, Germany. Google Scholar
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