Ethyl N-(2-benzoyl-4-chloro­phen­yl)­ethane­carboximidate

Sumathi, H.P.; Dayananda, A.S.; Dutkiewicz, G.; Yathirajan, H.S.; Kubicki, M.

doi:10.1107/S1600536812007763

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o916

doi:10.1107/S1600536812007763

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Ethyl N-(2-benzoyl-4-chlorophenyl)ethanecarboximidate

H. P. Sumathi,^a A. S. Dayananda,^a Grzegorz Dutkiewicz,^b H. S. Yathirajan ^a and Maciej Kubicki ^b ^*

^aDepartment of Studies in Chemistry, University of Mysore, Mysore 570 006, India, and ^bDepartment of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland
^*Correspondence e-mail: mkubicki@amu.edu.pl

(Received 1 February 2012; accepted 21 February 2012; online 29 February 2012)

In the title compound, C₁₇H₁₆ClNO₂, the N=C—O—C—C fragment is planar within 0.029 (1) Å, and makes dihedral angles of 66.71 (8) and 59.61 (8)° with the planes of the chlorophenyl and benzoyl rings, respectively. The carbonyl C=O bond is not coplanar with either of the aromatic rings; it makes angles of 42.5 and 23.5° with the normals to the ring planes. In the crystal, very weak C—H⋯O, C—H⋯Cl, C—H⋯π and π–π [interplanar distance = 3.53 (1) Å] interactions are observed.

Related literature

For background to the medical applications of benzophenones, see, for instance: Evans et al. (1987 ); Revesz et al. (2004 ); Wiesner et al. (2002 ); Zeng et al. (2010 ). A similar structure has been described by Derieg et al. (1970 )

Experimental

Crystal data

C₁₇H₁₆ClNO₂
M_r = 301.76
Triclinic, $[P \overline 1]$
a = 7.9674 (11) Å
b = 8.6993 (17) Å
c = 11.596 (2) Å
α = 104.499 (17)°
β = 94.871 (14)°
γ = 95.001 (14)°
V = 770.4 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 295 K
0.35 × 0.2 × 0.15 mm

Data collection

Agilent Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.991, T_max = 1.000
13278 measured reflections
3377 independent reflections
2455 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.117
S = 1.05
3377 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

CgA denotes the centroid of the phenyl ring C1–C6.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O22ⁱ	0.93	2.80	3.704 (2)	164
C6—H6⋯O14ⁱⁱ	0.93	2.73	3.648 (2)	172
C16—H16B⋯O22ⁱⁱⁱ	0.96	2.66	3.614 (3)	171
C27—H27⋯Cl4^iv	0.93	2.88	3.739 (2)	154
C25—H25⋯CgA^v	0.93	2.90	3.744 (3)	151
Symmetry codes: (i) x, y+1, z; (ii) -x+2, -y+1, -z+1; (iii) x+1, y, z; (iv) x+1, y-1, z; (v) -x+2, -y+1, -z+2.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812007763/nk2143sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007763/nk2143Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812007763/nk2143Isup3.cml

checkCIF report

Comment top

Benzophenone and related analogues have been reported to act as antiallergic, anti-inflammatory, antiasthamatic, antimalarial, anti-microbial and antianaphylactic agents (Evans et al., 1987; Wiesner et al., 2002). The competence of benzophenones as chemotherapeutic agents, especially as inhibitors of HIV-1 reverse transcriptase RT, cancer and inflammation, is well established and their chemistry has been studied extensively (Revesz et al., 2004, Zeng et al., 2010). The title compound - N-(2-Benzoyl-4-chloro-phenyl)-acetimidic acid ethyl ester (1, Scheme 1) - is an intermediate in the synthesis of certain anxiolytic, anticonvulsant and sedative drugs.

The conformation of N-(2-Benzoyl-4-chloro-phenyl)-acetimidic acid ethyl ester (1, Scheme 1) can be described by the dihedral angles between the approximately planar fragments: two aromatic rings (A and B, cf. Fig. 1), and the N=C—O—C—C chain (C, which is planar within 0.029 (1) Å). All these angles are close to 60°: A/B 69.14 (5) °, A/C 66.71 (8) °, B/C 59.61 (8) °. Interestingly, the C21=O22 double bond is not coplanar with either A or B phenyl rings, the C2—C21(=O22)—C23 plane makes the dihedral angle 52.81 (6) ° with the ring A and 25.51 (8) ° with ring B. Quite similar conformation was observed in the crystal structure of related compound, 2-benzoyl-4-chloroformanilide triacetylhydrazide (Derieg et al., 1970).

In the crystal only some weak but directional C—H···O, C—H···Cl and C—H···π interaction can be found (cf. Table), and they to some extent influence the packing together with van der Waals interactions. Also the phenyl rings B from molecules related by the center of symmetry stack to some extent with the interplanar distance of ca 3.53 Å.

Related literature top

For general references on medical applications of benzophenones, see, for instance: Evans et al. (1987); Revesz et al. (2004); Wiesner et al. (2002); Zeng et al. (2010). A similar structure has been described by Derieg et al. (1970)

Experimental top

The title compound was obtained as a gift sample from R. L. Fine Chem., Bengaluru, India. The compound was recrystallized from dichloromethane by slow evaporation (m.p: 323 K).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Anisotropic ellipsoid representation of 1, drawn at 50% probability level.
	Fig. 2. The crystal packing as seen approximately along the a-axis direction. Weak C—H···Cl hydrogen bonds are depicted as dashed lines.

Ethyl N-(2-benzoyl-4-chlorophenyl)ethanecarboximidate top

Crystal data top

C₁₇H₁₆ClNO₂	Z = 2
M_r = 301.76	F(000) = 316
Triclinic, P1	D_x = 1.301 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 7.9674 (11) Å	Cell parameters from 1885 reflections
b = 8.6993 (17) Å	θ = 2.9–27.8°
c = 11.596 (2) Å	µ = 0.25 mm⁻¹
α = 104.499 (17)°	T = 295 K
β = 94.871 (14)°	Block, colourless
γ = 95.001 (14)°	0.35 × 0.2 × 0.15 mm
V = 770.4 (2) Å³

Data collection top

Agilent Xcalibur Eos diffractometer	3377 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2455 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 16.1544 pixels mm^-1	θ_max = 28.2°, θ_min = 3.0°
ω–scan	h = −10→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −11→11
T_min = 0.991, T_max = 1.000	l = −15→15
13278 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0479P)² + 0.1642P] where P = (F_o² + 2F_c²)/3
3377 reflections	(Δ/σ)_max = 0.001
192 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₇H₁₆ClNO₂	γ = 95.001 (14)°
M_r = 301.76	V = 770.4 (2) Å³
Triclinic, P1	Z = 2
a = 7.9674 (11) Å	Mo Kα radiation
b = 8.6993 (17) Å	µ = 0.25 mm⁻¹
c = 11.596 (2) Å	T = 295 K
α = 104.499 (17)°	0.35 × 0.2 × 0.15 mm
β = 94.871 (14)°

Data collection top

Agilent Xcalibur Eos diffractometer	3377 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2455 reflections with I > 2σ(I)
T_min = 0.991, T_max = 1.000	R_int = 0.028
13278 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.05	Δρ_max = 0.20 e Å⁻³
3377 reflections	Δρ_min = −0.21 e Å⁻³
192 parameters

Special details top

Experimental. Address for R L Fine Chemicals:

No 15, R L Fine Chem, KHB Industrial Area, Yelahanka New Town, Bengaluru-560 106, India. Website: http://www.rlfinechem.com

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
C1	0.7628 (2)	0.41768 (19)	0.70454 (14)	0.0376 (4)
C2	0.6659 (2)	0.33697 (19)	0.77071 (14)	0.0361 (4)
C3	0.5286 (2)	0.4041 (2)	0.82141 (15)	0.0411 (4)
H3	0.4601	0.3484	0.8619	0.049*
C4	0.4940 (2)	0.5531 (2)	0.81170 (15)	0.0422 (4)
Cl4	0.32629 (7)	0.63863 (7)	0.87998 (5)	0.0670 (2)
C5	0.5910 (2)	0.6367 (2)	0.74955 (16)	0.0464 (4)
H5	0.5671	0.7374	0.7439	0.056*
C6	0.7238 (2)	0.5683 (2)	0.69612 (16)	0.0463 (4)
H6	0.7890	0.6236	0.6535	0.056*
N11	0.90172 (18)	0.34957 (17)	0.65447 (13)	0.0428 (4)
C12	0.9091 (2)	0.3070 (2)	0.54356 (16)	0.0432 (4)
C13	0.7813 (3)	0.3131 (3)	0.44432 (18)	0.0663 (6)
H13A	0.6819	0.3528	0.4768	0.099*
H13B	0.7517	0.2077	0.3923	0.099*
H13C	0.8278	0.3828	0.3997	0.099*
O14	1.04660 (16)	0.24308 (16)	0.50072 (10)	0.0514 (3)
C15	1.1748 (3)	0.2175 (3)	0.58734 (18)	0.0611 (6)
H15A	1.1248	0.1528	0.6353	0.073*
H15B	1.2242	0.3191	0.6404	0.073*
C16	1.3068 (3)	0.1356 (3)	0.5231 (2)	0.0828 (8)
H16A	1.2558	0.0387	0.4668	0.124*
H16B	1.3885	0.1107	0.5794	0.124*
H16C	1.3621	0.2040	0.4810	0.124*
C21	0.7012 (2)	0.1754 (2)	0.78588 (15)	0.0398 (4)
O22	0.58787 (18)	0.06586 (16)	0.76157 (14)	0.0632 (4)
C23	0.8739 (2)	0.15418 (19)	0.83424 (14)	0.0368 (4)
C24	0.9812 (2)	0.2816 (2)	0.90603 (16)	0.0455 (4)
H24	0.9479	0.3840	0.9217	0.055*
C25	1.1373 (3)	0.2576 (3)	0.95454 (18)	0.0587 (5)
H25	1.2078	0.3432	1.0049	0.070*
C26	1.1892 (3)	0.1075 (3)	0.9288 (2)	0.0655 (6)
H26	1.2951	0.0917	0.9613	0.079*
C27	1.0850 (3)	−0.0190 (3)	0.8554 (2)	0.0672 (6)
H27	1.1214	−0.1202	0.8365	0.081*
C28	0.9271 (3)	0.0033 (2)	0.80965 (18)	0.0533 (5)
H28	0.8554	−0.0835	0.7619	0.064*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0369 (9)	0.0398 (9)	0.0377 (9)	0.0072 (7)	0.0026 (7)	0.0122 (7)
C2	0.0353 (9)	0.0371 (8)	0.0365 (8)	0.0070 (7)	0.0002 (7)	0.0111 (7)
C3	0.0375 (9)	0.0466 (10)	0.0428 (9)	0.0092 (8)	0.0051 (8)	0.0165 (8)
C4	0.0411 (10)	0.0466 (10)	0.0420 (9)	0.0175 (8)	0.0043 (8)	0.0133 (8)
Cl4	0.0666 (4)	0.0787 (4)	0.0720 (4)	0.0447 (3)	0.0256 (3)	0.0314 (3)
C5	0.0540 (11)	0.0403 (9)	0.0498 (10)	0.0164 (9)	0.0026 (9)	0.0181 (8)
C6	0.0505 (11)	0.0437 (10)	0.0520 (10)	0.0090 (9)	0.0088 (9)	0.0235 (8)
N11	0.0417 (8)	0.0502 (9)	0.0418 (8)	0.0141 (7)	0.0086 (7)	0.0174 (7)
C12	0.0384 (10)	0.0510 (10)	0.0443 (10)	0.0086 (8)	0.0075 (8)	0.0175 (8)
C13	0.0553 (13)	0.0958 (17)	0.0489 (11)	0.0261 (12)	0.0009 (10)	0.0165 (11)
O14	0.0427 (7)	0.0750 (9)	0.0404 (7)	0.0197 (7)	0.0082 (6)	0.0165 (6)
C15	0.0527 (12)	0.0842 (15)	0.0502 (11)	0.0284 (11)	0.0031 (10)	0.0184 (10)
C16	0.0640 (15)	0.118 (2)	0.0739 (15)	0.0435 (15)	0.0100 (13)	0.0262 (15)
C21	0.0429 (10)	0.0360 (9)	0.0418 (9)	0.0070 (8)	0.0063 (8)	0.0112 (7)
O22	0.0490 (8)	0.0447 (7)	0.0956 (11)	−0.0023 (7)	−0.0048 (8)	0.0242 (7)
C23	0.0421 (10)	0.0353 (8)	0.0375 (9)	0.0108 (7)	0.0074 (7)	0.0145 (7)
C24	0.0478 (11)	0.0410 (9)	0.0480 (10)	0.0105 (8)	0.0025 (9)	0.0114 (8)
C25	0.0486 (12)	0.0701 (14)	0.0584 (12)	0.0067 (10)	−0.0065 (10)	0.0223 (10)
C26	0.0476 (12)	0.0906 (17)	0.0721 (14)	0.0281 (12)	0.0055 (11)	0.0404 (13)
C27	0.0729 (15)	0.0616 (13)	0.0798 (15)	0.0405 (13)	0.0148 (13)	0.0286 (12)
C28	0.0621 (13)	0.0387 (10)	0.0623 (12)	0.0166 (9)	0.0062 (10)	0.0154 (9)

Geometric parameters (Å, º) top

C1—C2	1.398 (2)	C15—C16	1.472 (3)
C1—C6	1.398 (2)	C15—H15A	0.9700
C1—N11	1.402 (2)	C15—H15B	0.9700
C2—C3	1.390 (2)	C16—H16A	0.9600
C2—C21	1.506 (2)	C16—H16B	0.9600
C3—C4	1.379 (2)	C16—H16C	0.9600
C3—H3	0.9300	C21—O22	1.214 (2)
C4—C5	1.380 (3)	C21—C23	1.486 (2)
C4—Cl4	1.7391 (17)	C23—C24	1.380 (2)
C5—C6	1.376 (2)	C23—C28	1.383 (2)
C5—H5	0.9300	C24—C25	1.375 (3)
C6—H6	0.9300	C24—H24	0.9300
N11—C12	1.254 (2)	C25—C26	1.373 (3)
C12—O14	1.348 (2)	C25—H25	0.9300
C12—C13	1.485 (3)	C26—C27	1.370 (3)
C13—H13A	0.9600	C26—H26	0.9300
C13—H13B	0.9600	C27—C28	1.372 (3)
C13—H13C	0.9600	C27—H27	0.9300
O14—C15	1.442 (2)	C28—H28	0.9300

C2—C1—C6	118.80 (15)	C16—C15—H15A	109.9
C2—C1—N11	119.15 (14)	O14—C15—H15B	109.9
C6—C1—N11	121.95 (16)	C16—C15—H15B	109.9
C3—C2—C1	119.58 (15)	H15A—C15—H15B	108.3
C3—C2—C21	118.18 (15)	C15—C16—H16A	109.5
C1—C2—C21	122.20 (15)	C15—C16—H16B	109.5
C4—C3—C2	120.03 (16)	H16A—C16—H16B	109.5
C4—C3—H3	120.0	C15—C16—H16C	109.5
C2—C3—H3	120.0	H16A—C16—H16C	109.5
C3—C4—C5	121.20 (16)	H16B—C16—H16C	109.5
C3—C4—Cl4	119.55 (14)	O22—C21—C23	120.95 (16)
C5—C4—Cl4	119.25 (13)	O22—C21—C2	119.91 (16)
C6—C5—C4	118.86 (16)	C23—C21—C2	119.12 (15)
C6—C5—H5	120.6	C24—C23—C28	119.14 (17)
C4—C5—H5	120.6	C24—C23—C21	121.28 (15)
C5—C6—C1	121.44 (17)	C28—C23—C21	119.57 (16)
C5—C6—H6	119.3	C25—C24—C23	120.16 (17)
C1—C6—H6	119.3	C25—C24—H24	119.9
C12—N11—C1	122.68 (15)	C23—C24—H24	119.9
N11—C12—O14	119.97 (16)	C26—C25—C24	120.2 (2)
N11—C12—C13	129.03 (17)	C26—C25—H25	119.9
O14—C12—C13	110.99 (15)	C24—C25—H25	119.9
C12—C13—H13A	109.5	C27—C26—C25	120.0 (2)
C12—C13—H13B	109.5	C27—C26—H26	120.0
H13A—C13—H13B	109.5	C25—C26—H26	120.0
C12—C13—H13C	109.5	C26—C27—C28	120.08 (19)
H13A—C13—H13C	109.5	C26—C27—H27	120.0
H13B—C13—H13C	109.5	C28—C27—H27	120.0
C12—O14—C15	116.82 (14)	C27—C28—C23	120.4 (2)
O14—C15—C16	108.70 (17)	C27—C28—H28	119.8
O14—C15—H15A	109.9	C23—C28—H28	119.8

C6—C1—C2—C3	3.2 (2)	C13—C12—O14—C15	−174.91 (18)
N11—C1—C2—C3	179.56 (15)	C12—O14—C15—C16	175.44 (19)
C6—C1—C2—C21	−179.05 (16)	C3—C2—C21—O22	50.6 (2)
N11—C1—C2—C21	−2.6 (2)	C1—C2—C21—O22	−127.22 (19)
C1—C2—C3—C4	−3.4 (2)	C3—C2—C21—C23	−127.49 (17)
C21—C2—C3—C4	178.69 (16)	C1—C2—C21—C23	54.7 (2)
C2—C3—C4—C5	1.7 (3)	O22—C21—C23—C24	−153.15 (17)
C2—C3—C4—Cl4	−177.78 (13)	C2—C21—C23—C24	24.9 (2)
C3—C4—C5—C6	0.4 (3)	O22—C21—C23—C28	25.1 (3)
Cl4—C4—C5—C6	179.81 (14)	C2—C21—C23—C28	−156.77 (16)
C4—C5—C6—C1	−0.6 (3)	C28—C23—C24—C25	−1.5 (3)
C2—C1—C6—C5	−1.2 (3)	C21—C23—C24—C25	176.78 (17)
N11—C1—C6—C5	−177.46 (16)	C23—C24—C25—C26	2.0 (3)
C2—C1—N11—C12	116.53 (19)	C24—C25—C26—C27	−0.5 (3)
C6—C1—N11—C12	−67.2 (2)	C25—C26—C27—C28	−1.5 (3)
C1—N11—C12—O14	179.59 (15)	C26—C27—C28—C23	2.0 (3)
C1—N11—C12—C13	−1.7 (3)	C24—C23—C28—C27	−0.5 (3)
N11—C12—O14—C15	4.1 (3)	C21—C23—C28—C27	−178.80 (18)

Hydrogen-bond geometry (Å, º) top

CgA denotes the centroid of the phenyl ring C1 - C6

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O22ⁱ	0.93	2.80	3.704 (2)	164
C6—H6···O14ⁱⁱ	0.93	2.73	3.648 (2)	172
C16—H16B···O22ⁱⁱⁱ	0.96	2.66	3.614 (3)	171
C27—H27···Cl4^iv	0.93	2.88	3.739 (2)	154
C25—H25···CgA^v	0.93	2.90	3.744 (3)	151

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆ClNO₂
M_r	301.76
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.9674 (11), 8.6993 (17), 11.596 (2)
α, β, γ (°)	104.499 (17), 94.871 (14), 95.001 (14)
V (Å³)	770.4 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.35 × 0.2 × 0.15

Data collection
Diffractometer	Agilent Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.991, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13278, 3377, 2455
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.664

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.117, 1.05
No. of reflections	3377
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.21

Computer programs: CrysAlis PRO (Agilent, 2011), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

CgA denotes the centroid of the phenyl ring C1 - C6

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O22ⁱ	0.93	2.80	3.704 (2)	164
C6—H6···O14ⁱⁱ	0.93	2.73	3.648 (2)	172
C16—H16B···O22ⁱⁱⁱ	0.96	2.66	3.614 (3)	171
C27—H27···Cl4^iv	0.93	2.88	3.739 (2)	154
C25—H25···CgA^v	0.93	2.90	3.744 (3)	151

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

Acknowledgements

ASD thanks the University of Mysore for research facilities. HSY thanks R. L. Fine Chem, Bengaluru, India, for the gift sample of the title compound.

References

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