5-(3-Chloro­phen­yl)-2-phenyl-3,4-dihydro-2H-pyrrole

Yang, G.; Su, X.; Lv, L.

doi:10.1107/S160053681003847X

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2782

https://doi.org/10.1107/S160053681003847X

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5-(3-Chlorophenyl)-2-phenyl-3,4-dihydro-2H-pyrrole

Guiqiu Yang,^a ^* Xiaoqing Su ^a and Liang Lv ^b

^aShenyang Universtity of Chemical Technology, Shenyang 110142, People's Republic of China, and ^bAgrochemicals Division, Shenyang Research Institute of Chemical Industry, Shenyang 110021, People's Republic of China
^*Correspondence e-mail: yangguiqiu@gmail.com

(Received 25 September 2010; accepted 26 September 2010; online 9 October 2010)

In the title compound, C₁₆H₁₄ClN, the conformation of the five-membered ring approximates to an envelope with a C atom as the flap. The dihedral angle between the aromatic rings is 78.71 (9)°.

Related literature

For chemical background to pyrrolines, see: Tsuge et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₄ClN
M_r = 255.73
Monoclinic, P 2₁ /c
a = 18.2543 (18) Å
b = 5.6398 (5) Å
c = 13.0095 (13) Å
β = 97.129 (2)°
V = 1329.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 296 K
0.38 × 0.32 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.905, T_max = 0.948
6409 measured reflections
2344 independent reflections
1856 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.091
S = 1.06
2344 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; 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: https://doi.org/10.1107/S160053681003847X/hb5651sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681003847X/hb5651Isup2.hkl

checkCIF report

Related literature top

For chemical background to pyrrolines, see: Tsuge et al. (1987).

Experimental top

To a 500 ml flask N-(4-(3-chlorophenyl)-4-oxo-1-phenylbutyl)acetamide (6.25 g, 19.79 mmol), 40 mL 6M Hydrochloric acid aqueous solution and 120 ml e thanol were added sequentially. The reaction mixture was heated to reflux and reacted for 20 h. After separation through silica gel column chromatography (fluent: ethyl acetate/petroleum ether=1/20), The title product compound was gained as a pale yellow solid (3.50 g, 69%) and recrystallised from methylene chloride to yield colourless blocks of (I).

Anal. Calcd for C₁₆H₁₄Cl₁N₁: C, 75.14; H, 5.52; Cl, 13.86; N, 5.48. Found: C, 75.22; H, 5.50; N, 5.45. ¹H NMR(CDCl3): 1.94(m,1H, N—CH—CH₁),2.83 (m,1H, N—CH—CH₁), 3.02(m, 1H, N=C—CH₁), 3.15 (m, 1H, N=C—CH₁), 5.33 (t, 1H,C=N—CH₁),7.28–7.88(m, 9H, Ph—H).

Structure description top

For chemical background to pyrrolines, see: Tsuge et al. (1987).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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. The molecular structure of (I), with 30% probability displacement ellipsoids.
	Fig. 2. Crystal packing of (I).

5-(3-Chlorophenyl)-2-phenyl-3,4-dihydro-2H-pyrrole top

Crystal data top

C₁₆H₁₄ClN	F(000) = 536
M_r = 255.73	D_x = 1.278 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2445 reflections
a = 18.2543 (18) Å	θ = 3.2–25.0°
b = 5.6398 (5) Å	µ = 0.27 mm⁻¹
c = 13.0095 (13) Å	T = 296 K
β = 97.129 (2)°	Block, colourless
V = 1329.0 (2) Å³	0.38 × 0.32 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	2344 independent reflections
Radiation source: fine-focus sealed tube	1856 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
phi and ω scans	θ_max = 25.0°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −21→21
T_min = 0.905, T_max = 0.948	k = −6→4
6409 measured reflections	l = −14→15

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0407P)² + 0.239P] where P = (F_o² + 2F_c²)/3
2344 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₆H₁₄ClN	V = 1329.0 (2) Å³
M_r = 255.73	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 18.2543 (18) Å	µ = 0.27 mm⁻¹
b = 5.6398 (5) Å	T = 296 K
c = 13.0095 (13) Å	0.38 × 0.32 × 0.20 mm
β = 97.129 (2)°

Data collection top

Bruker SMART CCD diffractometer	2344 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1856 reflections with I > 2σ(I)
T_min = 0.905, T_max = 0.948	R_int = 0.017
6409 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.06	Δρ_max = 0.13 e Å⁻³
2344 reflections	Δρ_min = −0.18 e Å⁻³
163 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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.46600 (3)	−0.37904 (9)	0.67127 (4)	0.07239 (19)
N1	0.26607 (7)	0.2985 (3)	0.70282 (10)	0.0606 (4)
C1	0.36885 (8)	−0.0215 (3)	0.63059 (11)	0.0477 (4)
H1	0.3644	−0.0242	0.7010	0.057*
C2	0.41540 (8)	−0.1765 (3)	0.59008 (12)	0.0514 (4)
C3	0.42310 (9)	−0.1765 (4)	0.48568 (13)	0.0625 (5)
H3	0.4547	−0.2834	0.4591	0.075*
C4	0.38333 (9)	−0.0163 (4)	0.42214 (13)	0.0669 (5)
H4	0.3883	−0.0140	0.3518	0.080*
C5	0.33616 (9)	0.1414 (3)	0.46108 (12)	0.0573 (4)
H5	0.3096	0.2492	0.4170	0.069*
C6	0.32813 (8)	0.1401 (3)	0.56578 (11)	0.0462 (4)
C7	0.27682 (8)	0.3056 (3)	0.60801 (11)	0.0480 (4)
C8	0.23478 (9)	0.4944 (3)	0.54365 (13)	0.0548 (4)
H8A	0.2677	0.6161	0.5233	0.066*
H8B	0.2070	0.4274	0.4820	0.066*
C9	0.18419 (12)	0.5915 (4)	0.61625 (14)	0.0760 (6)
H9A	0.1337	0.5408	0.5957	0.091*
H9B	0.1857	0.7635	0.6174	0.091*
C10	0.21413 (9)	0.4885 (3)	0.72331 (13)	0.0589 (4)
H10	0.2420	0.6131	0.7636	0.071*
C11	0.15575 (8)	0.3978 (3)	0.78499 (12)	0.0505 (4)
C12	0.13832 (10)	0.5176 (3)	0.87106 (13)	0.0601 (5)
H12	0.1635	0.6565	0.8916	0.072*
C13	0.08427 (11)	0.4353 (4)	0.92721 (16)	0.0761 (6)
H13	0.0735	0.5184	0.9852	0.091*
C14	0.04680 (11)	0.2338 (4)	0.89818 (18)	0.0795 (6)
H14	0.0102	0.1793	0.9360	0.095*
C15	0.06289 (12)	0.1112 (4)	0.8137 (2)	0.0839 (6)
H15	0.0373	−0.0272	0.7937	0.101*
C16	0.11725 (11)	0.1926 (4)	0.75748 (16)	0.0719 (5)
H16	0.1281	0.1073	0.7001	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0734 (3)	0.0730 (3)	0.0733 (3)	0.0237 (2)	0.0194 (2)	0.0061 (2)
N1	0.0599 (8)	0.0775 (10)	0.0437 (8)	0.0241 (8)	0.0038 (6)	−0.0048 (7)
C1	0.0469 (8)	0.0571 (10)	0.0401 (8)	−0.0006 (7)	0.0087 (6)	−0.0050 (7)
C2	0.0442 (8)	0.0575 (10)	0.0536 (9)	−0.0003 (7)	0.0105 (7)	−0.0047 (8)
C3	0.0532 (9)	0.0790 (13)	0.0581 (10)	0.0053 (9)	0.0177 (8)	−0.0161 (10)
C4	0.0605 (10)	0.1011 (15)	0.0413 (9)	0.0014 (10)	0.0155 (8)	−0.0081 (10)
C5	0.0534 (9)	0.0760 (12)	0.0425 (9)	0.0009 (9)	0.0064 (7)	0.0010 (8)
C6	0.0426 (8)	0.0557 (10)	0.0402 (8)	−0.0028 (7)	0.0046 (6)	−0.0057 (7)
C7	0.0467 (8)	0.0550 (10)	0.0415 (8)	0.0014 (7)	0.0019 (6)	−0.0047 (7)
C8	0.0580 (9)	0.0512 (10)	0.0542 (9)	−0.0003 (8)	0.0031 (8)	0.0030 (8)
C9	0.0848 (13)	0.0769 (14)	0.0667 (12)	0.0310 (11)	0.0118 (10)	0.0077 (10)
C10	0.0606 (10)	0.0617 (11)	0.0543 (10)	0.0154 (9)	0.0061 (8)	−0.0110 (9)
C11	0.0526 (9)	0.0463 (9)	0.0503 (9)	0.0123 (7)	−0.0026 (7)	−0.0103 (7)
C12	0.0645 (10)	0.0562 (11)	0.0597 (10)	0.0026 (9)	0.0080 (8)	−0.0168 (9)
C13	0.0760 (13)	0.0863 (15)	0.0690 (12)	0.0065 (11)	0.0213 (10)	−0.0087 (11)
C14	0.0666 (12)	0.0777 (15)	0.0946 (16)	0.0033 (11)	0.0111 (11)	0.0177 (13)
C15	0.0753 (13)	0.0512 (12)	0.1202 (19)	−0.0043 (10)	−0.0082 (13)	−0.0044 (12)
C16	0.0749 (12)	0.0584 (12)	0.0803 (13)	0.0084 (10)	0.0011 (10)	−0.0247 (10)

Geometric parameters (Å, º) top

Cl1—C2	1.7410 (17)	C8—H8B	0.9700
N1—C7	1.2733 (19)	C9—C10	1.545 (2)
N1—C10	1.477 (2)	C9—H9A	0.9700
C1—C2	1.369 (2)	C9—H9B	0.9700
C1—C6	1.392 (2)	C10—C11	1.501 (2)
C1—H1	0.9300	C10—H10	0.9800
C2—C3	1.383 (2)	C11—C16	1.378 (2)
C3—C4	1.370 (3)	C11—C12	1.378 (2)
C3—H3	0.9300	C12—C13	1.379 (3)
C4—C5	1.377 (2)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.356 (3)
C5—C6	1.388 (2)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.361 (3)
C6—C7	1.476 (2)	C14—H14	0.9300
C7—C8	1.505 (2)	C15—C16	1.382 (3)
C8—C9	1.504 (2)	C15—H15	0.9300
C8—H8A	0.9700	C16—H16	0.9300

C7—N1—C10	109.37 (14)	C8—C9—H9A	110.8
C2—C1—C6	119.66 (14)	C10—C9—H9A	110.8
C2—C1—H1	120.2	C8—C9—H9B	110.8
C6—C1—H1	120.2	C10—C9—H9B	110.8
C1—C2—C3	121.45 (16)	H9A—C9—H9B	108.9
C1—C2—Cl1	119.55 (12)	N1—C10—C11	111.31 (15)
C3—C2—Cl1	119.01 (13)	N1—C10—C9	105.86 (13)
C4—C3—C2	118.80 (16)	C11—C10—C9	114.51 (14)
C4—C3—H3	120.6	N1—C10—H10	108.3
C2—C3—H3	120.6	C11—C10—H10	108.3
C3—C4—C5	120.82 (15)	C9—C10—H10	108.3
C3—C4—H4	119.6	C16—C11—C12	117.45 (17)
C5—C4—H4	119.6	C16—C11—C10	121.35 (15)
C4—C5—C6	120.29 (16)	C12—C11—C10	121.19 (16)
C4—C5—H5	119.9	C11—C12—C13	121.18 (18)
C6—C5—H5	119.9	C11—C12—H12	119.4
C5—C6—C1	118.98 (15)	C13—C12—H12	119.4
C5—C6—C7	120.74 (15)	C14—C13—C12	120.27 (19)
C1—C6—C7	120.28 (13)	C14—C13—H13	119.9
N1—C7—C6	121.47 (14)	C12—C13—H13	119.9
N1—C7—C8	115.58 (14)	C13—C14—C15	119.9 (2)
C6—C7—C8	122.94 (13)	C13—C14—H14	120.0
C9—C8—C7	102.64 (14)	C15—C14—H14	120.0
C9—C8—H8A	111.2	C14—C15—C16	120.0 (2)
C7—C8—H8A	111.2	C14—C15—H15	120.0
C9—C8—H8B	111.2	C16—C15—H15	120.0
C7—C8—H8B	111.2	C11—C16—C15	121.21 (18)
H8A—C8—H8B	109.2	C11—C16—H16	119.4
C8—C9—C10	104.67 (14)	C15—C16—H16	119.4

C6—C1—C2—C3	0.0 (2)	C7—C8—C9—C10	12.4 (2)
C6—C1—C2—Cl1	−179.78 (12)	C7—N1—C10—C11	134.21 (15)
C1—C2—C3—C4	0.4 (3)	C7—N1—C10—C9	9.2 (2)
Cl1—C2—C3—C4	−179.80 (14)	C8—C9—C10—N1	−13.5 (2)
C2—C3—C4—C5	−0.4 (3)	C8—C9—C10—C11	−136.50 (16)
C3—C4—C5—C6	−0.1 (3)	N1—C10—C11—C16	−48.5 (2)
C4—C5—C6—C1	0.5 (2)	C9—C10—C11—C16	71.5 (2)
C4—C5—C6—C7	−178.99 (16)	N1—C10—C11—C12	131.90 (16)
C2—C1—C6—C5	−0.5 (2)	C9—C10—C11—C12	−108.09 (19)
C2—C1—C6—C7	179.01 (14)	C16—C11—C12—C13	−0.2 (3)
C10—N1—C7—C6	178.25 (14)	C10—C11—C12—C13	179.46 (17)
C10—N1—C7—C8	−1.0 (2)	C11—C12—C13—C14	−0.3 (3)
C5—C6—C7—N1	176.41 (16)	C12—C13—C14—C15	0.4 (3)
C1—C6—C7—N1	−3.0 (2)	C13—C14—C15—C16	−0.1 (3)
C5—C6—C7—C8	−4.4 (2)	C12—C11—C16—C15	0.5 (3)
C1—C6—C7—C8	176.10 (14)	C10—C11—C16—C15	−179.16 (17)
N1—C7—C8—C9	−7.8 (2)	C14—C15—C16—C11	−0.3 (3)
C6—C7—C8—C9	173.00 (15)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄ClN
M_r	255.73
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	18.2543 (18), 5.6398 (5), 13.0095 (13)
β (°)	97.129 (2)
V (Å³)	1329.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.38 × 0.32 × 0.20

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.905, 0.948
No. of measured, independent and observed [I > 2σ(I)] reflections	6409, 2344, 1856
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.091, 1.06
No. of reflections	2344
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.18

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tsuge, O., Ueno, K., Kanemasa, S. & Yorozu, K. (1987). Bull. Chem. Soc. Jpn, 60, 3347–3358. CrossRef CAS Web of Science Google Scholar