A second monoclinic polymorph of 1-benzyl-N-methyl-1H-pyrrole-2-carboxamide.

In the title compound, C(13)H(14)N(2)O, the N(pyrrole)-C(H(2))-C-C torsion angle is -7.7 (3)° and the dihedral angle between the pyrrole and benzene rings is 83.6 (2)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains extending along the c axis. We have previously reported another polymorphic form of this title compound, which has the same space group with different cell parameters: a = 9.8285 (18) Å, b = 23.588 (4) Å, c = 9.9230 (17) Å, β = 90.107 (3)°, Z = 8 and V = 2300.5 (7) Å(3) [Zeng et al. (2010 ▶). Acta Cryst. E66, o2051].

Related literature

For details of the synthesis, see: Zeng et al. (2010 ▶); For the previously reported polymorph, see: Zeng et al. (2010 ▶) and for a related structure, see: Zeng et al. (2007 ▶).

Experimental

Crystal data

C13H14N2O

M = 214.26

Monoclinic,

a = 5.4326 (4) Å

b = 22.5218 (16) Å

c = 9.7358 (5) Å

β = 101.676 (6)°

V = 1166.55 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.50 × 0.28 × 0.19 mm

Data collection

Oxford Gemini S Ultra area-detector diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.962, T max = 0.985

5327 measured reflections

2504 independent reflections

1597 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.169

S = 1.02

2504 reflections

150 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.16 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811030364/zk2014sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030364/zk2014Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030364/zk2014Isup3.cml

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

C13H14N2O	Dx = 1.220 Mg m−3
Mr = 214.26	Melting point: 360 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.4326 (4) Å	Cell parameters from 1936 reflections
b = 22.5218 (16) Å	θ = 3.5–29.2°
c = 9.7358 (5) Å	µ = 0.08 mm−1
β = 101.676 (6)°	T = 293 K
V = 1166.55 (13) Å3	Prism, colorless
Z = 4	0.50 × 0.28 × 0.19 mm
F(000) = 456

Oxford Gemini S Ultra area-detector diffractometer	2504 independent reflections
Radiation source: fine-focus sealed tube	1597 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 27.0°, θmin = 3.5°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	h = −6→6
Tmin = 0.962, Tmax = 0.985	k = −28→22
5327 measured reflections	l = −12→11

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0629P)2 + 0.3194P] where P = (Fo2 + 2Fc2)/3
2504 reflections	(Δ/σ)max = 0.004
150 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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.

	x	y	z	Uiso*/Ueq
C5	0.0889 (4)	0.28312 (9)	0.60936 (19)	0.0517 (5)
C4	0.2716 (4)	0.32716 (10)	0.6779 (2)	0.0543 (5)
N1	0.4311 (3)	0.35726 (9)	0.6084 (2)	0.0652 (5)
O1	0.0465 (4)	0.27429 (8)	0.48276 (15)	0.0877 (6)
N2	−0.0360 (4)	0.25434 (9)	0.6916 (2)	0.0688 (6)
C8	0.2613 (4)	0.39425 (10)	0.3667 (2)	0.0590 (6)
C7	0.4436 (5)	0.35414 (12)	0.4599 (2)	0.0729 (7)
H7A	0.4117	0.3135	0.4281	0.088*
H7B	0.6127	0.3643	0.4501	0.088*
C9	0.0783 (4)	0.42544 (11)	0.4135 (3)	0.0681 (6)
H9	0.0665	0.4229	0.5073	0.082*
C3	0.3192 (5)	0.34701 (11)	0.8140 (2)	0.0719 (7)
H3	0.2398	0.3342	0.8848	0.086*
C1	0.5712 (5)	0.39542 (13)	0.6999 (3)	0.0870 (8)
H1	0.6916	0.4213	0.6787	0.104*
C11	−0.0747 (6)	0.46500 (12)	0.1851 (3)	0.0847 (8)
H11	−0.1872	0.4888	0.1244	0.102*
C6	−0.2303 (5)	0.21166 (12)	0.6402 (3)	0.0819 (8)
H6A	−0.3890	0.2266	0.6541	0.123*
H6B	−0.1930	0.1750	0.6903	0.123*
H6C	−0.2385	0.2050	0.5420	0.123*
C12	0.1055 (6)	0.43425 (15)	0.1372 (3)	0.0962 (9)
H12	0.1160	0.4368	0.0432	0.115*
C10	−0.0895 (5)	0.46073 (12)	0.3229 (3)	0.0799 (7)
H10	−0.2130	0.4816	0.3561	0.096*
C13	0.2726 (5)	0.39933 (13)	0.2273 (3)	0.0830 (8)
H13	0.3960	0.3787	0.1933	0.100*
C2	0.5084 (5)	0.38987 (14)	0.8271 (3)	0.0911 (9)
H2	0.5783	0.4107	0.9080	0.109*
H2A	0.002 (5)	0.2599 (12)	0.781 (3)	0.092 (9)*

	U11	U22	U33	U12	U13	U23
C5	0.0605 (12)	0.0601 (13)	0.0343 (9)	0.0096 (10)	0.0092 (8)	0.0024 (9)
C4	0.0544 (12)	0.0661 (13)	0.0408 (10)	0.0075 (10)	0.0060 (8)	0.0031 (9)
N1	0.0503 (10)	0.0815 (14)	0.0631 (11)	0.0025 (10)	0.0095 (9)	0.0076 (10)
O1	0.1194 (15)	0.1092 (14)	0.0364 (8)	−0.0265 (12)	0.0205 (8)	−0.0120 (8)
N2	0.0875 (15)	0.0786 (14)	0.0402 (10)	−0.0144 (11)	0.0126 (10)	0.0021 (10)
C8	0.0509 (12)	0.0652 (14)	0.0648 (13)	−0.0049 (10)	0.0206 (10)	0.0075 (11)
C7	0.0605 (14)	0.0972 (19)	0.0682 (14)	0.0108 (13)	0.0297 (11)	0.0171 (13)
C9	0.0659 (14)	0.0742 (15)	0.0658 (14)	0.0021 (12)	0.0176 (11)	0.0046 (12)
C3	0.0807 (17)	0.0841 (17)	0.0457 (12)	0.0007 (14)	0.0000 (11)	−0.0033 (11)
C1	0.0592 (15)	0.097 (2)	0.096 (2)	−0.0110 (14)	−0.0053 (14)	0.0067 (17)
C11	0.091 (2)	0.0721 (17)	0.0839 (19)	0.0001 (15)	0.0011 (15)	0.0179 (14)
C6	0.0880 (19)	0.0753 (17)	0.0811 (17)	−0.0126 (14)	0.0140 (14)	0.0068 (13)
C12	0.107 (2)	0.114 (2)	0.0689 (17)	0.005 (2)	0.0211 (16)	0.0241 (17)
C10	0.0772 (17)	0.0731 (16)	0.0878 (18)	0.0086 (14)	0.0127 (14)	−0.0016 (15)
C13	0.0811 (18)	0.103 (2)	0.0721 (16)	0.0089 (16)	0.0330 (14)	0.0104 (15)
C2	0.0860 (19)	0.097 (2)	0.0756 (18)	−0.0090 (17)	−0.0194 (15)	−0.0136 (16)

C5—O1	1.223 (2)	C3—C2	1.397 (4)
C5—N2	1.320 (3)	C3—H3	0.9300
C5—C4	1.465 (3)	C1—C2	1.355 (4)
C4—C3	1.372 (3)	C1—H1	0.9300
C4—N1	1.381 (3)	C11—C12	1.356 (4)
N1—C1	1.356 (3)	C11—C10	1.363 (4)
N1—C7	1.462 (3)	C11—H11	0.9300
N2—C6	1.440 (3)	C6—H6A	0.9600
N2—H2A	0.86 (3)	C6—H6B	0.9600
C8—C9	1.369 (3)	C6—H6C	0.9600
C8—C13	1.376 (3)	C12—C13	1.374 (4)
C8—C7	1.502 (3)	C12—H12	0.9300
C7—H7A	0.9700	C10—H10	0.9300
C7—H7B	0.9700	C13—H13	0.9300
C9—C10	1.384 (3)	C2—H2	0.9300
C9—H9	0.9300
O1—C5—N2	121.1 (2)	C2—C3—H3	126.1
O1—C5—C4	122.79 (19)	C2—C1—N1	109.3 (2)
N2—C5—C4	116.09 (18)	C2—C1—H1	125.4
C3—C4—N1	107.4 (2)	N1—C1—H1	125.4
C3—C4—C5	129.7 (2)	C12—C11—C10	119.5 (3)
N1—C4—C5	122.89 (17)	C12—C11—H11	120.3
C1—N1—C4	108.3 (2)	C10—C11—H11	120.3
C1—N1—C7	123.2 (2)	N2—C6—H6A	109.5
C4—N1—C7	128.4 (2)	N2—C6—H6B	109.5
C5—N2—C6	123.2 (2)	H6A—C6—H6B	109.5
C5—N2—H2A	119.7 (19)	N2—C6—H6C	109.5
C6—N2—H2A	117.1 (18)	H6A—C6—H6C	109.5
C9—C8—C13	117.8 (2)	H6B—C6—H6C	109.5
C9—C8—C7	122.8 (2)	C11—C12—C13	120.2 (3)
C13—C8—C7	119.4 (2)	C11—C12—H12	119.9
N1—C7—C8	114.28 (19)	C13—C12—H12	119.9
N1—C7—H7A	108.7	C11—C10—C9	120.4 (3)
C8—C7—H7A	108.7	C11—C10—H10	119.8
N1—C7—H7B	108.7	C9—C10—H10	119.8
C8—C7—H7B	108.7	C12—C13—C8	121.4 (3)
H7A—C7—H7B	107.6	C12—C13—H13	119.3
C8—C9—C10	120.8 (2)	C8—C13—H13	119.3
C8—C9—H9	119.6	C1—C2—C3	107.3 (2)
C10—C9—H9	119.6	C1—C2—H2	126.3
C4—C3—C2	107.7 (2)	C3—C2—H2	126.3
C4—C3—H3	126.1
O1—C5—C4—C3	171.6 (2)	C13—C8—C9—C10	0.1 (4)
N2—C5—C4—C3	−6.1 (3)	C7—C8—C9—C10	−178.4 (2)
O1—C5—C4—N1	−7.8 (3)	N1—C4—C3—C2	0.4 (3)
N2—C5—C4—N1	174.51 (19)	C5—C4—C3—C2	−179.1 (2)
C3—C4—N1—C1	−0.8 (3)	C4—N1—C1—C2	1.0 (3)
C5—C4—N1—C1	178.7 (2)	C7—N1—C1—C2	176.9 (2)
C3—C4—N1—C7	−176.4 (2)	C10—C11—C12—C13	−0.4 (5)
C5—C4—N1—C7	3.0 (3)	C12—C11—C10—C9	0.2 (4)
O1—C5—N2—C6	−0.7 (4)	C8—C9—C10—C11	−0.1 (4)
C4—C5—N2—C6	177.0 (2)	C11—C12—C13—C8	0.5 (5)
C1—N1—C7—C8	−90.4 (3)	C9—C8—C13—C12	−0.3 (4)
C4—N1—C7—C8	84.7 (3)	C7—C8—C13—C12	178.3 (3)
C9—C8—C7—N1	−7.7 (3)	N1—C1—C2—C3	−0.7 (3)
C13—C8—C7—N1	173.8 (2)	C4—C3—C2—C1	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1i	0.86 (3)	2.08 (3)	2.852 (2)	149 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.86 (3)	2.08 (3)	2.852 (2)	149 (2)

Symmetry code: (i) .