Ethyl 1,4-bis-(4-chloro-phen-yl)-2-methyl-1H-pyrrole-3-carboxyl-ate.

In the title mol-ecule, C20H17Cl2NO2, the pyrrole moiety makes dihedral angles of 63.42 (11) and 70.43 (12)° with the chlorobenzene rings. The eth-oxy-carbonyl unit is present in a synperiplanar conformation with respect to the pyrrole ring, as indicated by the dihedral angle of 14.5 (3)°. In the crystal, mol-ecules are linked into chains parallel to the a-axis direction by weak C-H⋯O hydrogen bonds.

Related literature

For the biological importance of pyrroles, see: Banwell et al. (2006 ▶); Mohamed et al. (2009 ▶); Sosa et al. (2002 ▶).

Experimental

Crystal data

C20H17Cl2NO2

M = 374.25

Triclinic,

a = 8.037 (2) Å

b = 9.797 (3) Å

c = 12.510 (4) Å

α = 72.774 (16)°

β = 86.838 (16)°

γ = 76.804 (16)°

V = 915.9 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.37 mm−1

T = 296 K

0.15 × 0.15 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.947, T max = 0.947

15843 measured reflections

4196 independent reflections

2759 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.125

S = 1.03

4196 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813019247/fb2292sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019247/fb2292Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019247/fb2292Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H17Cl2NO2	Z = 2
Mr = 374.25	F(000) = 388
Triclinic, P1	Dx = 1.357 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.037 (2) Å	Cell parameters from 4196 reflections
b = 9.797 (3) Å	θ = 1.7–27.5°
c = 12.510 (4) Å	µ = 0.37 mm−1
α = 72.774 (16)°	T = 296 K
β = 86.838 (16)°	Block, yellow
γ = 76.804 (16)°	0.15 × 0.15 × 0.15 mm
V = 915.9 (5) Å3

Bruker SMART APEXII CCD area-detector diffractometer	4196 independent reflections
Radiation source: fine-focus sealed tube	2759 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω and φ scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −10→10
Tmin = 0.947, Tmax = 0.947	k = −12→12
15843 measured reflections	l = −16→16

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: difference Fourier map
wR(F2) = 0.125	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0487P)2 + 0.2827P] where P = (Fo2 + 2Fc2)/3
4196 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.29 e Å−3
66 constraints

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.

	x	y	z	Uiso*/Ueq
Cl18	0.20768 (10)	0.57041 (7)	0.24828 (5)	0.0884 (2)
Cl25	0.78934 (10)	−0.46743 (9)	1.16162 (6)	0.1057 (3)
O9	−0.18070 (16)	0.14269 (16)	0.59033 (12)	0.0585 (4)
O8	−0.27098 (18)	0.0253 (2)	0.75691 (13)	0.0735 (5)
N1	0.2589 (2)	−0.07110 (19)	0.83555 (13)	0.0521 (4)
C13	0.1310 (3)	0.2004 (2)	0.46496 (17)	0.0554 (5)
H13	0.1005	0.1157	0.4616	0.067*
C12	0.1613 (2)	0.2151 (2)	0.56891 (15)	0.0458 (4)
C3	0.1594 (2)	0.0973 (2)	0.67518 (15)	0.0470 (4)
C7	−0.1558 (2)	0.0648 (2)	0.69825 (16)	0.0498 (5)
C4	0.0231 (2)	0.0321 (2)	0.73283 (15)	0.0458 (4)
C15	0.1876 (3)	0.4336 (2)	0.37081 (17)	0.0562 (5)
C17	0.2025 (3)	0.3436 (2)	0.56978 (17)	0.0554 (5)
H17	0.2219	0.3576	0.6380	0.066*
C14	0.1448 (3)	0.3078 (2)	0.36672 (17)	0.0589 (5)
H14	0.1251	0.2949	0.2982	0.071*
C19	0.3838 (2)	−0.1689 (2)	0.91686 (16)	0.0505 (5)
C2	0.2999 (2)	0.0304 (2)	0.74178 (16)	0.0533 (5)
H2	0.4079	0.0502	0.7263	0.064*
C22	0.6316 (3)	−0.3508 (3)	1.06663 (17)	0.0615 (6)
C16	0.2157 (3)	0.4528 (2)	0.47182 (19)	0.0640 (6)
H16	0.2436	0.5388	0.4746	0.077*
C6	0.0083 (3)	−0.1721 (3)	0.92294 (19)	0.0655 (6)
H6A	−0.0078	−0.1366	0.9874	0.098*
H6B	0.0816	−0.2684	0.9426	0.098*
H6C	−0.1003	−0.1764	0.8973	0.098*
C5	0.0887 (2)	−0.0707 (2)	0.83166 (16)	0.0501 (5)
C23	0.6287 (3)	−0.3663 (3)	0.9623 (2)	0.0794 (8)
H23	0.7100	−0.4383	0.9421	0.095*
C20	0.3894 (3)	−0.1548 (3)	1.02199 (18)	0.0664 (6)
H20	0.3088	−0.0826	1.0424	0.080*
C21	0.5134 (3)	−0.2469 (3)	1.09782 (18)	0.0690 (6)
H21	0.5162	−0.2381	1.1697	0.083*
C24	0.5039 (3)	−0.2739 (3)	0.88682 (18)	0.0721 (7)
H24	0.5014	−0.2832	0.8151	0.087*
C10	−0.3529 (3)	0.1775 (3)	0.54626 (19)	0.0698 (6)
H10A	−0.4272	0.2462	0.5798	0.084*
H10B	−0.3972	0.0894	0.5630	0.084*
C11	−0.3464 (3)	0.2438 (3)	0.4224 (2)	0.0822 (8)
H11A	−0.3013	0.3303	0.4068	0.123*
H11B	−0.4596	0.2694	0.3910	0.123*
H11C	−0.2742	0.1744	0.3900	0.123*

	U11	U22	U33	U12	U13	U23
Cl18	0.1196 (6)	0.0733 (4)	0.0583 (4)	−0.0226 (4)	0.0054 (3)	0.0019 (3)
Cl25	0.1053 (6)	0.1152 (6)	0.0738 (4)	0.0282 (4)	−0.0484 (4)	−0.0242 (4)
O8	0.0469 (8)	0.1037 (13)	0.0608 (9)	−0.0179 (8)	0.0010 (7)	−0.0098 (9)
O9	0.0441 (7)	0.0719 (10)	0.0534 (8)	−0.0092 (7)	−0.0091 (6)	−0.0103 (7)
N1	0.0445 (9)	0.0604 (10)	0.0448 (9)	−0.0098 (7)	−0.0067 (7)	−0.0056 (8)
C2	0.0458 (11)	0.0623 (13)	0.0474 (11)	−0.0157 (9)	−0.0044 (8)	−0.0057 (10)
C3	0.0447 (10)	0.0518 (11)	0.0444 (10)	−0.0085 (8)	−0.0044 (8)	−0.0146 (9)
C4	0.0431 (10)	0.0495 (11)	0.0440 (10)	−0.0073 (8)	−0.0011 (8)	−0.0143 (9)
C5	0.0445 (10)	0.0551 (12)	0.0495 (11)	−0.0099 (9)	−0.0014 (8)	−0.0141 (9)
C6	0.0567 (13)	0.0673 (15)	0.0614 (14)	−0.0137 (11)	0.0008 (10)	−0.0022 (11)
C7	0.0471 (11)	0.0542 (12)	0.0470 (11)	−0.0065 (9)	−0.0031 (9)	−0.0163 (9)
C10	0.0461 (11)	0.0895 (17)	0.0670 (14)	−0.0050 (11)	−0.0159 (10)	−0.0172 (13)
C11	0.0730 (16)	0.104 (2)	0.0638 (15)	−0.0006 (14)	−0.0226 (12)	−0.0256 (14)
C12	0.0391 (9)	0.0498 (11)	0.0454 (10)	−0.0043 (8)	−0.0050 (7)	−0.0126 (9)
C13	0.0609 (12)	0.0560 (12)	0.0521 (12)	−0.0145 (10)	−0.0025 (9)	−0.0181 (10)
C14	0.0657 (13)	0.0681 (14)	0.0432 (11)	−0.0131 (11)	−0.0025 (9)	−0.0177 (10)
C15	0.0562 (12)	0.0538 (12)	0.0487 (11)	−0.0031 (9)	0.0008 (9)	−0.0072 (10)
C16	0.0803 (15)	0.0499 (12)	0.0617 (14)	−0.0140 (11)	−0.0046 (11)	−0.0157 (11)
C17	0.0637 (13)	0.0549 (13)	0.0474 (11)	−0.0092 (10)	−0.0085 (9)	−0.0161 (10)
C19	0.0464 (10)	0.0563 (12)	0.0429 (10)	−0.0089 (9)	−0.0073 (8)	−0.0059 (9)
C20	0.0676 (14)	0.0734 (15)	0.0534 (13)	0.0026 (11)	−0.0073 (10)	−0.0238 (11)
C21	0.0756 (15)	0.0849 (17)	0.0443 (11)	−0.0051 (13)	−0.0134 (10)	−0.0225 (12)
C22	0.0628 (13)	0.0675 (14)	0.0463 (11)	−0.0038 (11)	−0.0170 (9)	−0.0098 (10)
C23	0.0809 (16)	0.0853 (18)	0.0589 (14)	0.0205 (13)	−0.0208 (12)	−0.0267 (13)
C24	0.0764 (15)	0.0865 (17)	0.0474 (12)	0.0090 (13)	−0.0181 (10)	−0.0275 (12)

Cl18—C15	1.740 (2)	C19—C24	1.366 (3)
Cl25—C22	1.739 (3)	C20—C21	1.376 (3)
O8—C7	1.211 (2)	C21—C22	1.358 (4)
O9—C7	1.340 (2)	C22—C23	1.360 (3)
O9—C10	1.447 (3)	C23—C24	1.379 (4)
N1—C2	1.375 (3)	C2—H2	0.9300
N1—C5	1.371 (2)	C6—H6A	0.9600
N1—C19	1.434 (3)	C6—H6B	0.9600
C2—C3	1.357 (3)	C6—H6C	0.9600
C3—C4	1.445 (2)	C10—H10A	0.9700
C3—C12	1.482 (3)	C10—H10B	0.9700
C4—C5	1.383 (3)	C11—H11A	0.9600
C4—C7	1.461 (2)	C11—H11B	0.9600
C5—C6	1.499 (3)	C11—H11C	0.9600
C10—C11	1.495 (3)	C13—H13	0.9300
C12—C13	1.390 (3)	C14—H14	0.9300
C12—C17	1.376 (3)	C16—H16	0.9300
C13—C14	1.379 (3)	C17—H17	0.9300
C14—C15	1.369 (3)	C20—H20	0.9300
C15—C16	1.369 (3)	C21—H21	0.9300
C16—C17	1.385 (3)	C23—H23	0.9300
C19—C20	1.367 (3)	C24—H24	0.9300
Cl18···C21i	3.505 (3)	C10···H2v	3.0500
Cl18···H23ii	3.0100	C10···H16vii	3.0400
Cl25···H17iii	3.0000	C11···H16vii	3.0700
O8···C6	3.041 (3)	C15···H11Bx	2.9100
O8···C20iv	3.377 (3)	C17···H10Ax	2.9100
O9···C12	2.971 (2)	C19···H6B	2.7900
O9···C13	2.957 (3)	H2···O8x	2.5800
O8···H10A	2.7200	H2···C10x	3.0500
O8···H10B	2.5300	H2···H10Bx	2.5000
O8···H20iv	2.7200	H6B···C19	2.7900
O8···H21iv	2.8500	H6C···O8	2.4200
O8···H2v	2.5800	H6C···C7	2.8500
O8···H6C	2.4200	H10A···O8	2.7200
O9···H13	2.7100	H10A···C17v	2.9100
O9···H13vi	2.7300	H10B···O8	2.5300
O9···H16vii	2.9100	H10B···H2v	2.5000
C6···O8	3.041 (3)	H11A···H16vii	2.3500
C6···C20	3.424 (4)	H11B···C15v	2.9100
C12···O9	2.971 (2)	H11B···H24vi	2.5800
C13···O9	2.957 (3)	H11C···C2vi	3.0000
C15···C17vii	3.567 (3)	H11C···C3vi	2.9500
C16···C17vii	3.473 (3)	H13···O9	2.7100
C16···C16vii	3.468 (4)	H13···O9vi	2.7300
C17···C15vii	3.567 (3)	H13···C7vi	2.9900
C17···C16vii	3.473 (3)	H16···O9vii	2.9100
C20···O8iv	3.377 (3)	H16···C10vii	3.0400
C20···C6	3.424 (4)	H16···C11vii	3.0700
C21···Cl18viii	3.505 (3)	H16···H11Avii	2.3500
C23···C23ix	3.582 (4)	H17···C2	3.0100
C2···H11Cvi	3.0000	H17···Cl25iii	3.0000
C2···H24	3.0200	H20···O8iv	2.7200
C2···H17	3.0100	H21···O8iv	2.8500
C3···H11Cvi	2.9500	H23···Cl18ii	3.0100
C7···H13vi	2.9900	H24···C2	3.0200
C7···H6C	2.8500	H24···H11Bvi	2.5800
C7—O9—C10	116.77 (15)	C19—C24—C23	120.4 (2)
C2—N1—C5	109.47 (16)	N1—C2—H2	125.00
C2—N1—C19	122.99 (16)	C3—C2—H2	125.00
C5—N1—C19	127.29 (16)	C5—C6—H6A	109.00
N1—C2—C3	109.90 (16)	C5—C6—H6B	109.00
C2—C3—C4	105.42 (16)	C5—C6—H6C	109.00
C2—C3—C12	122.85 (16)	H6A—C6—H6B	109.00
C4—C3—C12	131.70 (16)	H6A—C6—H6C	110.00
C3—C4—C5	108.37 (15)	H6B—C6—H6C	109.00
C3—C4—C7	128.27 (17)	O9—C10—H10A	110.00
C5—C4—C7	123.36 (16)	O9—C10—H10B	110.00
N1—C5—C4	106.84 (16)	C11—C10—H10A	110.00
N1—C5—C6	121.23 (18)	C11—C10—H10B	110.00
C4—C5—C6	131.92 (17)	H10A—C10—H10B	108.00
O8—C7—O9	122.15 (17)	C10—C11—H11A	109.00
O8—C7—C4	125.71 (18)	C10—C11—H11B	109.00
O9—C7—C4	112.13 (15)	C10—C11—H11C	109.00
O9—C10—C11	107.67 (19)	H11A—C11—H11B	109.00
C3—C12—C13	123.03 (18)	H11A—C11—H11C	110.00
C3—C12—C17	119.97 (17)	H11B—C11—H11C	110.00
C13—C12—C17	116.92 (18)	C12—C13—H13	119.00
C12—C13—C14	121.90 (19)	C14—C13—H13	119.00
C13—C14—C15	119.53 (19)	C13—C14—H14	120.00
Cl18—C15—C14	120.60 (16)	C15—C14—H14	120.00
Cl18—C15—C16	119.25 (17)	C15—C16—H16	120.00
C14—C15—C16	120.15 (19)	C17—C16—H16	120.00
C15—C16—C17	119.7 (2)	C12—C17—H17	119.00
C12—C17—C16	121.80 (19)	C16—C17—H17	119.00
N1—C19—C20	121.23 (19)	C19—C20—H20	120.00
N1—C19—C24	119.19 (18)	C21—C20—H20	120.00
C20—C19—C24	119.5 (2)	C20—C21—H21	120.00
C19—C20—C21	120.4 (2)	C22—C21—H21	120.00
C20—C21—C22	119.3 (2)	C22—C23—H23	120.00
Cl25—C22—C21	119.70 (17)	C24—C23—H23	120.00
Cl25—C22—C23	119.1 (2)	C19—C24—H24	120.00
C21—C22—C23	121.2 (2)	C23—C24—H24	120.00
C22—C23—C24	119.2 (3)
C10—O9—C7—O8	−0.2 (3)	C7—C4—C5—C6	1.5 (4)
C10—O9—C7—C4	178.21 (19)	C3—C4—C7—O8	−167.2 (2)
C7—O9—C10—C11	−171.6 (2)	C3—C4—C7—O9	14.5 (3)
C5—N1—C2—C3	−0.5 (2)	C5—C4—C7—O8	12.2 (3)
C19—N1—C2—C3	174.18 (18)	C5—C4—C7—O9	−166.22 (19)
C2—N1—C5—C4	0.6 (2)	C3—C12—C13—C14	−175.6 (2)
C2—N1—C5—C6	179.4 (2)	C17—C12—C13—C14	1.3 (3)
C19—N1—C5—C4	−173.79 (19)	C3—C12—C17—C16	176.1 (2)
C19—N1—C5—C6	5.0 (3)	C13—C12—C17—C16	−0.9 (3)
C2—N1—C19—C20	110.8 (2)	C12—C13—C14—C15	−0.8 (4)
C2—N1—C19—C24	−66.3 (3)	C13—C14—C15—Cl18	179.48 (19)
C5—N1—C19—C20	−75.4 (3)	C13—C14—C15—C16	−0.3 (4)
C5—N1—C19—C24	107.5 (2)	Cl18—C15—C16—C17	−179.05 (19)
N1—C2—C3—C4	0.2 (2)	C14—C15—C16—C17	0.7 (4)
N1—C2—C3—C12	178.42 (18)	C15—C16—C17—C12	−0.1 (4)
C2—C3—C4—C5	0.2 (2)	N1—C19—C20—C21	−178.0 (2)
C2—C3—C4—C7	179.6 (2)	C24—C19—C20—C21	−1.0 (4)
C12—C3—C4—C5	−177.8 (2)	N1—C19—C24—C23	177.9 (2)
C12—C3—C4—C7	1.6 (4)	C20—C19—C24—C23	0.8 (4)
C2—C3—C12—C13	116.0 (2)	C19—C20—C21—C22	0.9 (4)
C2—C3—C12—C17	−60.8 (3)	C20—C21—C22—Cl25	179.8 (2)
C4—C3—C12—C13	−66.3 (3)	C20—C21—C22—C23	−0.6 (4)
C4—C3—C12—C17	116.9 (2)	Cl25—C22—C23—C24	−179.9 (2)
C3—C4—C5—N1	−0.5 (2)	C21—C22—C23—C24	0.5 (4)
C3—C4—C5—C6	−179.1 (2)	C22—C23—C24—C19	−0.6 (4)
C7—C4—C5—N1	−179.95 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O8x	0.93	2.58	3.453 (3)	157
C6—H6C···O8	0.96	2.42	3.041 (3)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O8i	0.93	2.58	3.453 (3)	157
C6—H6C⋯O8	0.96	2.42	3.041 (3)	122

Symmetry code: (i) .