3-(4-Chloro­phen­yl)-1-(2-methyl-4-phenyl­quinolin-3-yl)prop-2-en-1-one

Prasath, R.; Bhavana, P.; Butcher, R.J.; Jasinski, J.P.

doi:10.1107/S1600536811004661

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o621

doi:10.1107/S1600536811004661

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3-(4-Chlorophenyl)-1-(2-methyl-4-phenylquinolin-3-yl)prop-2-en-1-one

R. Prasath,^a P. Bhavana,^a Ray J. Butcher ^b ^* and Jerry P. Jasinski ^c

^aChemistry Group, BITS, Pilani, K. K. Birla Goa Campus, Goa 403 726, India, ^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and ^cDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
^*Correspondence e-mail: rbutcher99@yahoo.com

(Received 30 January 2011; accepted 7 February 2011; online 12 February 2011)

The crystal structure of the title compound, C₂₅H₁₈ClNO, shows that the molecules are isolated and not involved in intermolecular C—H⋯O or C—H⋯Cl interactions. However, the phenyl and quinoline rings are involved in π–π interactions [centroid–centroid distance = 3.8829 (9) Å].

Related literature

For background details and the biological activity of quinolines, see: Markees et al. (1970 ); Campbell et al. (1998 ); Bhat et al. (2005 ). For the biological activity of chalcones, see: Wu et al. (2006 ).

Experimental

Crystal data

C₂₅H₁₈ClNO
M_r = 383.85
Triclinic, $[P \overline 1]$
a = 6.5376 (2) Å
b = 10.0345 (4) Å
c = 15.6545 (6) Å
α = 90.845 (3)°
β = 95.521 (3)°
γ = 107.035 (3)°
V = 976.36 (6) Å³
Z = 2
Cu Kα radiation
μ = 1.84 mm⁻¹
T = 295 K
0.52 × 0.18 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO, CrysAlis RED and CrysAlis CCD. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.544, T_max = 1.000
7607 measured reflections
4065 independent reflections
3402 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.160
S = 1.04
4065 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO, CrysAlis RED and CrysAlis CCD. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811004661/ez2231sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811004661/ez2231Isup2.hkl

checkCIF report

Comment top

Quinoline derivatives are very important compounds because of their wide occurrence in natural products and biologically active compounds (Markees et al., 1970; Campbell et al., 1998). Additionally, chalcone derivatives are attracting the increasing interest of many researchers, because of their bioactivity such as antimicrobial, antimalarial, anticancer, antiviral, antitumor activities (Bhat et al., 2005). Introduction of the quinoline scaffold into chalcone compounds can bring about significant changes in biological effects (Wu et al., 2006).

The crystal structure of the title compound shows that the molecules are isolated and not involved in intermolecular interactions. However, both the phenyl ring and the quinoline rings are involved in π–π interactions (centroid to centroid distances of 3.428 (2) and 3.770 (2) Å, respectively).

Related literature top

For background details and the biological activity of quinolines, see: Markees et al. (1970); Campbell et al. (1998); Bhat et al. (2005. For the biological activity of chalcones, see: Wu et al. (2006).

Experimental top

A mixture of 3-acetyl-2-methyl-4-phenylquinoline (2.61 g, 0.01 M), 4-chlorobenzaldehyde (1.40 g, 0.01 M) and KOH (1.12 g, 0.02 M ) in distilled ethanol (20 ml) was stirred for 12 h at room temperature. The resulting mixture was neutralized with dilute acetic acid. The resultant solid was filtered, dried and purified by column chromatography using 1:1 mixture of ethyl acetate and hexane. Re-crystallization was by slow evaporation of acetone solution of (I) which yielded colourless needle type crystals. M.pt. 453-455 K. Yield: 72%.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Diagram of the title compound, C₂₅H₁₈ClNO, showing atom labeling.
	Fig. 2. The molecular packing for C₂₅H₁₈ClNO viewed down the a axis.

3-(4-Chlorophenyl)-1-(2-methyl-4-phenylquinolin-3-yl)prop-2-en-1-one top

Crystal data top

C₂₅H₁₈ClNO	Z = 2
M_r = 383.85	F(000) = 400
Triclinic, P1	D_x = 1.306 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 6.5376 (2) Å	Cell parameters from 4929 reflections
b = 10.0345 (4) Å	θ = 5.3–77.1°
c = 15.6545 (6) Å	µ = 1.84 mm⁻¹
α = 90.845 (3)°	T = 295 K
β = 95.521 (3)°	Needle, colorless
γ = 107.035 (3)°	0.52 × 0.18 × 0.12 mm
V = 976.36 (6) Å³

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	4065 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3402 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
Detector resolution: 10.5081 pixels mm^-1	θ_max = 77.4°, θ_min = 5.3°
ω scans	h = −3→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −12→12
T_min = 0.544, T_max = 1.000	l = −19→19
7607 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1125P)² + 0.0628P] where P = (F_o² + 2F_c²)/3
4065 reflections	(Δ/σ)_max = 0.001
254 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₅H₁₈ClNO	γ = 107.035 (3)°
M_r = 383.85	V = 976.36 (6) Å³
Triclinic, P1	Z = 2
a = 6.5376 (2) Å	Cu Kα radiation
b = 10.0345 (4) Å	µ = 1.84 mm⁻¹
c = 15.6545 (6) Å	T = 295 K
α = 90.845 (3)°	0.52 × 0.18 × 0.12 mm
β = 95.521 (3)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	4065 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	3402 reflections with I > 2σ(I)
T_min = 0.544, T_max = 1.000	R_int = 0.019
7607 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.04	Δρ_max = 0.29 e Å⁻³
4065 reflections	Δρ_min = −0.24 e Å⁻³
254 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
Cl	−0.41045 (10)	−0.24622 (7)	0.99317 (4)	0.1004 (3)
O	0.6524 (2)	0.15628 (12)	0.65464 (9)	0.0678 (3)
N	0.22876 (19)	0.41447 (12)	0.55076 (8)	0.0485 (3)
C1	0.0479 (2)	0.02060 (15)	0.82219 (9)	0.0505 (3)
C2	0.0750 (3)	−0.10510 (17)	0.85056 (12)	0.0603 (4)
H2A	0.1889	−0.1338	0.8340	0.072*
C3	−0.0651 (3)	−0.18756 (18)	0.90290 (12)	0.0671 (4)
H3A	−0.0465	−0.2714	0.9212	0.081*
C4	−0.2326 (3)	−0.14364 (19)	0.92754 (11)	0.0638 (4)
C5	−0.2633 (3)	−0.0196 (2)	0.90095 (13)	0.0696 (4)
H5A	−0.3765	0.0092	0.9181	0.083*
C6	−0.1218 (3)	0.06090 (18)	0.84822 (12)	0.0620 (4)
H6A	−0.1416	0.1444	0.8299	0.074*
C7	0.1907 (3)	0.11066 (14)	0.76588 (10)	0.0515 (3)
H7A	0.1646	0.1949	0.7532	0.062*
C8	0.3530 (3)	0.08465 (14)	0.73113 (10)	0.0543 (4)
H8A	0.3797	0.0001	0.7420	0.065*
C9	0.4934 (2)	0.18093 (14)	0.67652 (10)	0.0488 (3)
C10	0.4416 (2)	0.31192 (13)	0.64783 (8)	0.0434 (3)
C11	0.2682 (2)	0.30333 (14)	0.58322 (9)	0.0463 (3)
C12	0.1198 (3)	0.16483 (16)	0.54764 (11)	0.0588 (4)
H12A	0.0640	0.1744	0.4898	0.088*
H12B	0.0030	0.1345	0.5824	0.088*
H12C	0.1978	0.0973	0.5480	0.088*
C13	0.3573 (2)	0.54308 (14)	0.58070 (8)	0.0447 (3)
C14	0.3076 (3)	0.66120 (16)	0.54642 (10)	0.0547 (4)
H14A	0.1939	0.6494	0.5037	0.066*
C15	0.4265 (3)	0.79222 (17)	0.57609 (12)	0.0622 (4)
H15A	0.3928	0.8693	0.5535	0.075*
C16	0.5992 (3)	0.81211 (15)	0.64035 (12)	0.0596 (4)
H16A	0.6782	0.9020	0.6602	0.072*
C17	0.6522 (3)	0.70013 (15)	0.67399 (10)	0.0511 (3)
H17A	0.7675	0.7145	0.7162	0.061*
C18	0.5324 (2)	0.56215 (13)	0.64491 (8)	0.0422 (3)
C19	0.5751 (2)	0.44052 (13)	0.67829 (8)	0.0414 (3)
C20	0.7569 (2)	0.45328 (13)	0.74642 (8)	0.0437 (3)
C21	0.9681 (3)	0.50871 (19)	0.72893 (11)	0.0599 (4)
H21A	0.9977	0.5393	0.6744	0.072*
C22	1.1357 (3)	0.5186 (2)	0.79260 (14)	0.0710 (5)
H22A	1.2772	0.5567	0.7807	0.085*
C23	1.0937 (3)	0.4725 (2)	0.87317 (12)	0.0673 (5)
H23A	1.2066	0.4777	0.9153	0.081*
C24	0.8847 (3)	0.41878 (18)	0.89139 (11)	0.0623 (4)
H24A	0.8563	0.3886	0.9461	0.075*
C25	0.7164 (2)	0.40945 (15)	0.82857 (9)	0.0512 (3)
H25A	0.5753	0.3736	0.8414	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0863 (4)	0.1060 (5)	0.0916 (4)	−0.0055 (3)	0.0264 (3)	0.0365 (3)
O	0.0731 (7)	0.0532 (6)	0.0893 (8)	0.0308 (6)	0.0285 (6)	0.0164 (6)
N	0.0481 (6)	0.0462 (6)	0.0503 (6)	0.0133 (5)	0.0028 (5)	0.0012 (5)
C1	0.0537 (8)	0.0416 (7)	0.0515 (7)	0.0073 (6)	0.0036 (6)	0.0039 (5)
C2	0.0624 (9)	0.0487 (8)	0.0697 (10)	0.0146 (7)	0.0107 (7)	0.0116 (7)
C3	0.0731 (11)	0.0506 (8)	0.0718 (10)	0.0093 (7)	0.0057 (8)	0.0178 (7)
C4	0.0599 (9)	0.0639 (9)	0.0542 (8)	−0.0025 (7)	0.0051 (7)	0.0109 (7)
C5	0.0627 (10)	0.0746 (11)	0.0719 (11)	0.0178 (8)	0.0168 (8)	0.0097 (8)
C6	0.0667 (10)	0.0536 (8)	0.0677 (9)	0.0189 (7)	0.0126 (7)	0.0111 (7)
C7	0.0600 (8)	0.0358 (6)	0.0576 (8)	0.0121 (6)	0.0061 (6)	0.0067 (5)
C8	0.0636 (9)	0.0368 (6)	0.0634 (8)	0.0146 (6)	0.0107 (7)	0.0104 (6)
C9	0.0551 (8)	0.0377 (6)	0.0540 (7)	0.0135 (6)	0.0082 (6)	0.0043 (5)
C10	0.0478 (7)	0.0374 (6)	0.0460 (6)	0.0120 (5)	0.0112 (5)	0.0043 (5)
C11	0.0475 (7)	0.0404 (6)	0.0497 (7)	0.0102 (5)	0.0079 (5)	−0.0003 (5)
C12	0.0581 (8)	0.0442 (7)	0.0668 (9)	0.0065 (6)	−0.0008 (7)	−0.0035 (6)
C13	0.0488 (7)	0.0419 (6)	0.0454 (6)	0.0152 (5)	0.0093 (5)	0.0047 (5)
C14	0.0580 (8)	0.0511 (8)	0.0578 (8)	0.0214 (6)	0.0024 (6)	0.0100 (6)
C15	0.0742 (10)	0.0447 (7)	0.0734 (10)	0.0255 (7)	0.0080 (8)	0.0132 (7)
C16	0.0712 (10)	0.0368 (7)	0.0684 (9)	0.0124 (6)	0.0065 (7)	0.0008 (6)
C17	0.0579 (8)	0.0413 (7)	0.0522 (7)	0.0121 (6)	0.0040 (6)	0.0016 (5)
C18	0.0492 (7)	0.0374 (6)	0.0411 (6)	0.0127 (5)	0.0099 (5)	0.0036 (5)
C19	0.0466 (6)	0.0390 (6)	0.0403 (6)	0.0134 (5)	0.0099 (5)	0.0039 (5)
C20	0.0491 (7)	0.0386 (6)	0.0454 (6)	0.0153 (5)	0.0068 (5)	0.0021 (5)
C21	0.0529 (8)	0.0722 (10)	0.0563 (8)	0.0185 (7)	0.0134 (6)	0.0028 (7)
C22	0.0461 (8)	0.0879 (13)	0.0803 (12)	0.0219 (8)	0.0073 (8)	−0.0080 (9)
C23	0.0642 (10)	0.0716 (10)	0.0683 (10)	0.0301 (8)	−0.0129 (8)	−0.0077 (8)
C24	0.0742 (10)	0.0602 (9)	0.0508 (8)	0.0198 (8)	−0.0021 (7)	0.0065 (6)
C25	0.0544 (8)	0.0476 (7)	0.0488 (7)	0.0108 (6)	0.0058 (6)	0.0060 (5)

Geometric parameters (Å, º) top

Cl—C4	1.7399 (17)	C12—H12C	0.9600
O—C9	1.2149 (19)	C13—C18	1.4149 (19)
N—C11	1.3147 (18)	C13—C14	1.4173 (19)
N—C13	1.3646 (18)	C14—C15	1.365 (2)
C1—C6	1.380 (2)	C14—H14A	0.9300
C1—C2	1.397 (2)	C15—C16	1.403 (2)
C1—C7	1.467 (2)	C15—H15A	0.9300
C2—C3	1.384 (2)	C16—C17	1.367 (2)
C2—H2A	0.9300	C16—H16A	0.9300
C3—C4	1.379 (3)	C17—C18	1.4196 (19)
C3—H3A	0.9300	C17—H17A	0.9300
C4—C5	1.381 (3)	C18—C19	1.4253 (17)
C5—C6	1.385 (2)	C19—C20	1.4929 (18)
C5—H5A	0.9300	C20—C21	1.385 (2)
C6—H6A	0.9300	C20—C25	1.390 (2)
C7—C8	1.326 (2)	C21—C22	1.388 (2)
C7—H7A	0.9300	C21—H21A	0.9300
C8—C9	1.471 (2)	C22—C23	1.375 (3)
C8—H8A	0.9300	C22—H22A	0.9300
C9—C10	1.5142 (18)	C23—C24	1.374 (3)
C10—C19	1.3770 (18)	C23—H23A	0.9300
C10—C11	1.4267 (19)	C24—C25	1.384 (2)
C11—C12	1.5053 (19)	C24—H24A	0.9300
C12—H12A	0.9600	C25—H25A	0.9300
C12—H12B	0.9600

C11—N—C13	118.73 (12)	N—C13—C18	122.82 (12)
C6—C1—C2	118.20 (15)	N—C13—C14	117.62 (13)
C6—C1—C7	118.85 (14)	C18—C13—C14	119.55 (13)
C2—C1—C7	122.95 (14)	C15—C14—C13	120.05 (14)
C3—C2—C1	120.99 (16)	C15—C14—H14A	120.0
C3—C2—H2A	119.5	C13—C14—H14A	120.0
C1—C2—H2A	119.5	C14—C15—C16	120.79 (14)
C4—C3—C2	119.06 (16)	C14—C15—H15A	119.6
C4—C3—H3A	120.5	C16—C15—H15A	119.6
C2—C3—H3A	120.5	C17—C16—C15	120.43 (14)
C3—C4—C5	121.40 (16)	C17—C16—H16A	119.8
C3—C4—Cl	119.65 (14)	C15—C16—H16A	119.8
C5—C4—Cl	118.96 (15)	C16—C17—C18	120.51 (14)
C4—C5—C6	118.56 (17)	C16—C17—H17A	119.7
C4—C5—H5A	120.7	C18—C17—H17A	119.7
C6—C5—H5A	120.7	C13—C18—C17	118.66 (12)
C1—C6—C5	121.79 (16)	C13—C18—C19	117.70 (12)
C1—C6—H6A	119.1	C17—C18—C19	123.63 (13)
C5—C6—H6A	119.1	C10—C19—C18	118.40 (12)
C8—C7—C1	126.86 (13)	C10—C19—C20	121.16 (12)
C8—C7—H7A	116.6	C18—C19—C20	120.42 (11)
C1—C7—H7A	116.6	C21—C20—C25	118.93 (14)
C7—C8—C9	124.21 (13)	C21—C20—C19	120.71 (13)
C7—C8—H8A	117.9	C25—C20—C19	120.37 (13)
C9—C8—H8A	117.9	C20—C21—C22	120.14 (16)
O—C9—C8	120.17 (13)	C20—C21—H21A	119.9
O—C9—C10	119.62 (13)	C22—C21—H21A	119.9
C8—C9—C10	120.21 (12)	C23—C22—C21	120.37 (16)
C19—C10—C11	119.78 (12)	C23—C22—H22A	119.8
C19—C10—C9	119.63 (12)	C21—C22—H22A	119.8
C11—C10—C9	120.30 (12)	C24—C23—C22	119.90 (16)
N—C11—C10	122.56 (12)	C24—C23—H23A	120.1
N—C11—C12	116.00 (13)	C22—C23—H23A	120.1
C10—C11—C12	121.44 (13)	C23—C24—C25	120.18 (16)
C11—C12—H12A	109.5	C23—C24—H24A	119.9
C11—C12—H12B	109.5	C25—C24—H24A	119.9
H12A—C12—H12B	109.5	C24—C25—C20	120.47 (15)
C11—C12—H12C	109.5	C24—C25—H25A	119.8
H12A—C12—H12C	109.5	C20—C25—H25A	119.8
H12B—C12—H12C	109.5

C6—C1—C2—C3	0.4 (3)	C13—C14—C15—C16	0.2 (3)
C7—C1—C2—C3	−179.28 (15)	C14—C15—C16—C17	0.4 (3)
C1—C2—C3—C4	−0.5 (3)	C15—C16—C17—C18	−0.5 (3)
C2—C3—C4—C5	0.1 (3)	N—C13—C18—C17	−177.84 (13)
C2—C3—C4—Cl	179.88 (13)	C14—C13—C18—C17	0.8 (2)
C3—C4—C5—C6	0.2 (3)	N—C13—C18—C19	0.69 (19)
Cl—C4—C5—C6	−179.55 (14)	C14—C13—C18—C19	179.30 (12)
C2—C1—C6—C5	−0.1 (3)	C16—C17—C18—C13	−0.1 (2)
C7—C1—C6—C5	179.63 (16)	C16—C17—C18—C19	−178.57 (13)
C4—C5—C6—C1	−0.2 (3)	C11—C10—C19—C18	1.17 (19)
C6—C1—C7—C8	−176.02 (16)	C9—C10—C19—C18	174.99 (11)
C2—C1—C7—C8	3.7 (3)	C11—C10—C19—C20	179.45 (11)
C1—C7—C8—C9	−178.63 (14)	C9—C10—C19—C20	−6.74 (19)
C7—C8—C9—O	172.12 (16)	C13—C18—C19—C10	−1.45 (18)
C7—C8—C9—C10	−7.4 (2)	C17—C18—C19—C10	177.00 (13)
O—C9—C10—C19	−67.03 (19)	C13—C18—C19—C20	−179.74 (11)
C8—C9—C10—C19	112.49 (15)	C17—C18—C19—C20	−1.3 (2)
O—C9—C10—C11	106.75 (17)	C10—C19—C20—C21	114.65 (16)
C8—C9—C10—C11	−73.73 (18)	C18—C19—C20—C21	−67.11 (18)
C13—N—C11—C10	−0.7 (2)	C10—C19—C20—C25	−65.29 (17)
C13—N—C11—C12	179.73 (13)	C18—C19—C20—C25	112.95 (15)
C19—C10—C11—N	−0.1 (2)	C25—C20—C21—C22	0.6 (2)
C9—C10—C11—N	−173.84 (13)	C19—C20—C21—C22	−179.32 (15)
C19—C10—C11—C12	179.44 (13)	C20—C21—C22—C23	0.6 (3)
C9—C10—C11—C12	5.7 (2)	C21—C22—C23—C24	−1.3 (3)
C11—N—C13—C18	0.4 (2)	C22—C23—C24—C25	0.8 (3)
C11—N—C13—C14	−178.23 (13)	C23—C24—C25—C20	0.5 (2)
N—C13—C14—C15	177.86 (15)	C21—C20—C25—C24	−1.2 (2)
C18—C13—C14—C15	−0.8 (2)	C19—C20—C25—C24	178.80 (13)

Experimental details

Crystal data
Chemical formula	C₂₅H₁₈ClNO
M_r	383.85
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	6.5376 (2), 10.0345 (4), 15.6545 (6)
α, β, γ (°)	90.845 (3), 95.521 (3), 107.035 (3)
V (Å³)	976.36 (6)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	1.84
Crystal size (mm)	0.52 × 0.18 × 0.12

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.544, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7607, 4065, 3402
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.160, 1.04
No. of reflections	4065
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.24

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

RJB wishes to acknowledge the NSF–MRI program (grant CHE-0619278) for funds to purchase the diffractometer.

References

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