1-Benzyl-N-methyl-1H-pyrrole-2-carboxamide.

The asymmetric unit of the title compound, C(13)H(14)N(2)O, contains two independent mol-ecules, which differ in the twist of the phenyl ring: the N(pyrrole)-C(H(2))-C-C torsion angles are -73.0 (3) and 17.1 (3)°. In the crystal structure, mol-ecules are linked through N-H⋯O hydrogen bonds into chains extending along the a axis.

Related literature

For the bioactivity of pyrrole derivatives, see: Fabio et al. (2007 ▶); Banwell et al. (2006 ▶). For related structures, see: Zeng et al. (2007 ▶); Li et al. (2009 ▶).

Experimental

Crystal data

C13H14N2O

M = 214.26

Monoclinic,

a = 9.8285 (18) Å

b = 23.588 (4) Å

c = 9.9230 (17) Å

β = 90.107 (3)°

V = 2300.5 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 110 K

0.45 × 0.43 × 0.41 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.965, T max = 0.968

10728 measured reflections

4879 independent reflections

4388 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.157

S = 1.03

4879 reflections

300 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-Plus; 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 datablocks I, global. DOI: 10.1107/S160053681002787X/cv2741sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002787X/cv2741Isup2.hkl

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

C13H14N2O	Dx = 1.237 Mg m−3
Mr = 214.26	Melting point: 365 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.8285 (18) Å	Cell parameters from 7113 reflections
b = 23.588 (4) Å	θ = 2.2–27.0°
c = 9.9230 (17) Å	µ = 0.08 mm−1
β = 90.107 (3)°	T = 110 K
V = 2300.5 (7) Å3	Prism, colourless
Z = 8	0.45 × 0.43 × 0.41 mm
F(000) = 912

Bruker SMART 1K CCD area-detector diffractometer	4879 independent reflections
Radiation source: fine-focus sealed tube	4388 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.965, Tmax = 0.968	k = −30→18
10728 measured reflections	l = −8→12

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.157	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.1044P)2 + 0.2726P] where P = (Fo2 + 2Fc2)/3
4879 reflections	(Δ/σ)max = 0.001
300 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.32 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
O3	0.26038 (14)	0.34460 (7)	1.12858 (15)	0.0345 (4)
N4	0.46989 (19)	0.36072 (8)	1.21438 (18)	0.0298 (4)
O1	0.75946 (15)	0.35421 (7)	0.24801 (16)	0.0351 (4)
C18	0.38669 (19)	0.34269 (8)	1.11684 (19)	0.0248 (4)
N3	0.38660 (18)	0.31280 (7)	0.87447 (16)	0.0278 (4)
C5	0.8847 (2)	0.34954 (8)	0.2623 (2)	0.0261 (4)
C4	0.94580 (19)	0.32331 (7)	0.3830 (2)	0.0251 (4)
N1	0.87834 (18)	0.31770 (7)	0.50486 (17)	0.0284 (4)
C3	1.0677 (2)	0.29404 (8)	0.3945 (2)	0.0299 (4)
H3	1.1347	0.2903	0.3262	0.036*
C21	0.2777 (2)	0.39956 (8)	0.7816 (2)	0.0276 (4)
C17	0.4525 (2)	0.31943 (8)	0.9961 (2)	0.0254 (4)
N2	0.97245 (19)	0.36613 (8)	0.16790 (19)	0.0325 (4)
C7	0.7549 (2)	0.34689 (9)	0.5492 (2)	0.0318 (4)
H7A	0.7010	0.3207	0.6058	0.038*
H7B	0.6994	0.3564	0.4690	0.038*
C16	0.5796 (2)	0.29413 (8)	0.9852 (2)	0.0305 (4)
H16	0.6469	0.2920	1.0539	0.037*
C25	0.3206 (3)	0.49865 (10)	0.8254 (3)	0.0427 (5)
H25	0.3390	0.5284	0.8873	0.051*
C15	0.5903 (3)	0.27231 (9)	0.8536 (2)	0.0378 (5)
H15	0.6659	0.2525	0.8170	0.045*
C8	0.7817 (2)	0.40061 (8)	0.6283 (2)	0.0289 (4)
C20	0.2580 (2)	0.33927 (9)	0.8305 (2)	0.0305 (4)
H20A	0.1931	0.3393	0.9067	0.037*
H20B	0.2178	0.3163	0.7569	0.037*
C19	0.4191 (2)	0.37479 (11)	1.3473 (2)	0.0387 (5)
H19A	0.3238	0.3867	1.3404	0.058*
H19B	0.4735	0.4057	1.3855	0.058*
H19C	0.4256	0.3414	1.4058	0.058*
C11	0.8202 (3)	0.50016 (11)	0.7752 (3)	0.0442 (5)
H11	0.8334	0.5341	0.8251	0.053*
C1	0.9583 (3)	0.28673 (8)	0.5899 (2)	0.0355 (5)
H1	0.9366	0.2775	0.6805	0.043*
C14	0.4714 (3)	0.28490 (8)	0.7884 (2)	0.0345 (5)
H14	0.4511	0.2757	0.6974	0.041*
C22	0.2682 (2)	0.41183 (9)	0.6454 (2)	0.0338 (5)
H22	0.2501	0.3822	0.5830	0.041*
C26	0.3042 (2)	0.44347 (9)	0.8715 (2)	0.0371 (5)
H26	0.3111	0.4357	0.9652	0.044*
C6	0.9276 (3)	0.38588 (13)	0.0361 (3)	0.0497 (6)
H6A	0.8989	0.3534	−0.0186	0.075*
H6B	1.0027	0.4055	−0.0090	0.075*
H6C	0.8510	0.4120	0.0470	0.075*
C9	0.6769 (2)	0.42377 (10)	0.7042 (2)	0.0379 (5)
H9	0.5909	0.4054	0.7066	0.045*
C2	1.0749 (2)	0.27108 (8)	0.5242 (2)	0.0347 (5)
H2	1.1469	0.2488	0.5601	0.042*
C13	0.9061 (2)	0.42821 (10)	0.6273 (2)	0.0378 (5)
H13	0.9790	0.4132	0.5756	0.045*
C23	0.2847 (3)	0.46671 (10)	0.5993 (2)	0.0423 (5)
H23	0.2785	0.4746	0.5056	0.051*
C10	0.6962 (3)	0.47337 (11)	0.7765 (3)	0.0447 (6)
H10	0.6233	0.4889	0.8272	0.054*
C12	0.9253 (3)	0.47759 (11)	0.7011 (3)	0.0469 (6)
H12	1.0114	0.4959	0.7004	0.056*
C24	0.3101 (3)	0.51017 (10)	0.6894 (3)	0.0426 (5)
H24	0.3203	0.5479	0.6577	0.051*
H2A	1.058 (4)	0.3631 (12)	0.183 (3)	0.051 (8)*
H4	0.557 (3)	0.3597 (11)	1.204 (3)	0.044 (7)*

	U11	U22	U33	U12	U13	U23
O3	0.0196 (6)	0.0549 (9)	0.0290 (7)	−0.0027 (6)	0.0040 (6)	−0.0056 (7)
N4	0.0200 (8)	0.0428 (9)	0.0267 (8)	0.0019 (7)	0.0021 (7)	−0.0066 (7)
O1	0.0200 (7)	0.0510 (9)	0.0342 (7)	0.0021 (6)	−0.0005 (6)	0.0048 (7)
C18	0.0228 (8)	0.0286 (8)	0.0231 (8)	−0.0006 (7)	0.0033 (8)	0.0014 (7)
N3	0.0334 (9)	0.0271 (7)	0.0230 (7)	−0.0028 (6)	0.0040 (7)	−0.0011 (6)
C5	0.0221 (9)	0.0259 (8)	0.0301 (9)	0.0001 (7)	0.0010 (8)	−0.0020 (8)
C4	0.0235 (9)	0.0258 (8)	0.0261 (9)	−0.0012 (7)	0.0017 (8)	−0.0031 (7)
N1	0.0292 (8)	0.0297 (8)	0.0263 (8)	0.0001 (7)	0.0027 (7)	0.0007 (7)
C3	0.0288 (9)	0.0297 (9)	0.0311 (10)	0.0050 (7)	−0.0019 (9)	−0.0038 (8)
C21	0.0216 (8)	0.0337 (10)	0.0276 (9)	0.0015 (7)	0.0028 (8)	−0.0002 (8)
C17	0.0246 (9)	0.0269 (8)	0.0249 (9)	−0.0021 (7)	0.0063 (8)	0.0023 (7)
N2	0.0220 (8)	0.0439 (10)	0.0315 (9)	0.0032 (7)	0.0047 (7)	0.0066 (8)
C7	0.0251 (10)	0.0390 (11)	0.0313 (9)	−0.0027 (8)	0.0067 (9)	−0.0027 (8)
C16	0.0296 (10)	0.0313 (9)	0.0307 (10)	0.0058 (8)	0.0091 (9)	0.0047 (8)
C25	0.0439 (12)	0.0329 (10)	0.0512 (13)	0.0004 (9)	−0.0023 (12)	−0.0046 (10)
C15	0.0473 (13)	0.0321 (9)	0.0339 (11)	0.0097 (9)	0.0157 (10)	0.0006 (9)
C8	0.0275 (9)	0.0339 (9)	0.0251 (8)	0.0022 (8)	0.0007 (8)	0.0024 (8)
C20	0.0309 (10)	0.0345 (10)	0.0260 (8)	−0.0067 (8)	0.0001 (8)	−0.0001 (8)
C19	0.0307 (11)	0.0574 (13)	0.0280 (10)	0.0063 (10)	0.0003 (9)	−0.0112 (9)
C11	0.0467 (13)	0.0429 (12)	0.0431 (12)	0.0042 (10)	−0.0025 (11)	−0.0125 (10)
C1	0.0455 (13)	0.0323 (10)	0.0287 (10)	0.0005 (9)	−0.0043 (10)	0.0017 (8)
C14	0.0493 (13)	0.0276 (10)	0.0265 (9)	0.0036 (9)	0.0080 (10)	−0.0031 (8)
C22	0.0370 (11)	0.0386 (11)	0.0260 (9)	0.0064 (9)	0.0037 (8)	−0.0001 (9)
C26	0.0419 (12)	0.0367 (10)	0.0325 (10)	−0.0014 (9)	−0.0046 (10)	−0.0030 (9)
C6	0.0376 (12)	0.0753 (17)	0.0362 (11)	0.0101 (12)	0.0077 (11)	0.0211 (12)
C9	0.0288 (10)	0.0461 (12)	0.0387 (11)	0.0016 (9)	0.0055 (10)	−0.0029 (10)
C2	0.0395 (11)	0.0315 (10)	0.0329 (10)	0.0082 (9)	−0.0063 (9)	−0.0026 (8)
C13	0.0272 (10)	0.0441 (11)	0.0421 (11)	−0.0009 (9)	0.0057 (10)	−0.0089 (10)
C23	0.0497 (14)	0.0452 (12)	0.0320 (10)	0.0104 (10)	0.0063 (11)	0.0113 (10)
C10	0.0369 (12)	0.0518 (14)	0.0454 (13)	0.0097 (10)	0.0050 (11)	−0.0117 (11)
C12	0.0347 (12)	0.0497 (13)	0.0563 (15)	−0.0080 (10)	0.0001 (12)	−0.0131 (12)
C24	0.0402 (12)	0.0340 (11)	0.0536 (13)	0.0057 (9)	0.0065 (11)	0.0103 (10)

O3—C18	1.248 (2)	C15—C14	1.367 (4)
N4—C18	1.335 (3)	C15—H15	0.9500
N4—C19	1.450 (3)	C8—C13	1.386 (3)
N4—H4	0.87 (3)	C8—C9	1.390 (3)
O1—C5	1.243 (2)	C20—H20A	0.9900
C18—C17	1.469 (3)	C20—H20B	0.9900
N3—C14	1.364 (3)	C19—H19A	0.9800
N3—C17	1.378 (3)	C19—H19B	0.9800
N3—C20	1.475 (3)	C19—H19C	0.9800
C5—N2	1.334 (3)	C11—C10	1.373 (4)
C5—C4	1.475 (3)	C11—C12	1.376 (4)
C4—N1	1.386 (3)	C11—H11	0.9500
C4—C3	1.388 (3)	C1—C2	1.369 (3)
N1—C1	1.364 (3)	C1—H1	0.9500
N1—C7	1.463 (3)	C14—H14	0.9500
C3—C2	1.398 (3)	C22—C23	1.383 (3)
C3—H3	0.9500	C22—H22	0.9500
C21—C22	1.385 (3)	C26—H26	0.9500
C21—C26	1.391 (3)	C6—H6A	0.9800
C21—C20	1.515 (3)	C6—H6B	0.9800
C17—C16	1.389 (3)	C6—H6C	0.9800
N2—C6	1.456 (3)	C9—C10	1.385 (3)
N2—H2A	0.86 (4)	C9—H9	0.9500
C7—C8	1.513 (3)	C2—H2	0.9500
C7—H7A	0.9900	C13—C12	1.388 (3)
C7—H7B	0.9900	C13—H13	0.9500
C16—C15	1.408 (3)	C23—C24	1.383 (4)
C16—H16	0.9500	C23—H23	0.9500
C25—C24	1.381 (4)	C10—H10	0.9500
C25—C26	1.389 (3)	C12—H12	0.9500
C25—H25	0.9500	C24—H24	0.9500
C18—N4—C19	121.39 (18)	N3—C20—H20B	109.1
C18—N4—H4	120.7 (19)	C21—C20—H20B	109.1
C19—N4—H4	117.3 (19)	H20A—C20—H20B	107.8
O3—C18—N4	121.92 (18)	N4—C19—H19A	109.5
O3—C18—C17	121.96 (18)	N4—C19—H19B	109.5
N4—C18—C17	116.10 (17)	H19A—C19—H19B	109.5
C14—N3—C17	108.44 (18)	N4—C19—H19C	109.5
C14—N3—C20	122.93 (18)	H19A—C19—H19C	109.5
C17—N3—C20	127.76 (16)	H19B—C19—H19C	109.5
O1—C5—N2	122.4 (2)	C10—C11—C12	119.6 (2)
O1—C5—C4	122.11 (19)	C10—C11—H11	120.2
N2—C5—C4	115.51 (18)	C12—C11—H11	120.2
N1—C4—C3	107.17 (18)	N1—C1—C2	109.37 (19)
N1—C4—C5	123.61 (17)	N1—C1—H1	125.3
C3—C4—C5	128.74 (19)	C2—C1—H1	125.3
C1—N1—C4	108.33 (18)	N3—C14—C15	109.37 (19)
C1—N1—C7	122.91 (18)	N3—C14—H14	125.3
C4—N1—C7	127.97 (17)	C15—C14—H14	125.3
C4—C3—C2	108.07 (19)	C23—C22—C21	120.7 (2)
C4—C3—H3	126.0	C23—C22—H22	119.6
C2—C3—H3	126.0	C21—C22—H22	119.6
C22—C21—C26	118.8 (2)	C25—C26—C21	120.5 (2)
C22—C21—C20	120.01 (18)	C25—C26—H26	119.7
C26—C21—C20	121.14 (18)	C21—C26—H26	119.7
N3—C17—C16	107.72 (18)	N2—C6—H6A	109.5
N3—C17—C18	123.36 (17)	N2—C6—H6B	109.5
C16—C17—C18	128.44 (19)	H6A—C6—H6B	109.5
C5—N2—C6	122.00 (19)	N2—C6—H6C	109.5
C5—N2—H2A	119 (2)	H6A—C6—H6C	109.5
C6—N2—H2A	118 (2)	H6B—C6—H6C	109.5
N1—C7—C8	113.97 (17)	C10—C9—C8	120.8 (2)
N1—C7—H7A	108.8	C10—C9—H9	119.6
C8—C7—H7A	108.8	C8—C9—H9	119.6
N1—C7—H7B	108.8	C1—C2—C3	107.04 (19)
C8—C7—H7B	108.8	C1—C2—H2	126.5
H7A—C7—H7B	107.7	C3—C2—H2	126.5
C17—C16—C15	107.3 (2)	C8—C13—C12	120.6 (2)
C17—C16—H16	126.3	C8—C13—H13	119.7
C15—C16—H16	126.3	C12—C13—H13	119.7
C24—C25—C26	119.9 (2)	C24—C23—C22	120.1 (2)
C24—C25—H25	120.1	C24—C23—H23	120.0
C26—C25—H25	120.1	C22—C23—H23	120.0
C14—C15—C16	107.11 (19)	C11—C10—C9	120.3 (2)
C14—C15—H15	126.4	C11—C10—H10	119.8
C16—C15—H15	126.4	C9—C10—H10	119.8
C13—C8—C9	118.3 (2)	C11—C12—C13	120.4 (2)
C13—C8—C7	122.84 (19)	C11—C12—H12	119.8
C9—C8—C7	118.81 (19)	C13—C12—H12	119.8
N3—C20—C21	112.46 (16)	C25—C24—C23	119.9 (2)
N3—C20—H20A	109.1	C25—C24—H24	120.0
C21—C20—H20A	109.1	C23—C24—H24	120.0
C19—N4—C18—O3	10.3 (3)	N1—C7—C8—C9	−163.65 (18)
C19—N4—C18—C17	−168.55 (18)	C14—N3—C20—C21	−87.5 (2)
O1—C5—C4—N1	−20.5 (3)	C17—N3—C20—C21	80.6 (2)
N2—C5—C4—N1	161.67 (17)	C22—C21—C20—N3	107.6 (2)
O1—C5—C4—C3	150.5 (2)	C26—C21—C20—N3	−73.0 (3)
N2—C5—C4—C3	−27.3 (3)	C4—N1—C1—C2	−1.4 (2)
C3—C4—N1—C1	1.2 (2)	C7—N1—C1—C2	−171.95 (18)
C5—C4—N1—C1	173.90 (17)	C17—N3—C14—C15	1.3 (2)
C3—C4—N1—C7	171.15 (18)	C20—N3—C14—C15	171.34 (17)
C5—C4—N1—C7	−16.2 (3)	C16—C15—C14—N3	−0.9 (2)
N1—C4—C3—C2	−0.6 (2)	C26—C21—C22—C23	0.0 (3)
C5—C4—C3—C2	−172.77 (19)	C20—C21—C22—C23	179.4 (2)
C14—N3—C17—C16	−1.1 (2)	C24—C25—C26—C21	0.2 (4)
C20—N3—C17—C16	−170.53 (17)	C22—C21—C26—C25	0.1 (3)
C14—N3—C17—C18	−173.73 (17)	C20—C21—C26—C25	−179.3 (2)
C20—N3—C17—C18	16.8 (3)	C13—C8—C9—C10	0.3 (3)
O3—C18—C17—N3	18.7 (3)	C7—C8—C9—C10	−179.0 (2)
N4—C18—C17—N3	−162.52 (17)	N1—C1—C2—C3	1.0 (2)
O3—C18—C17—C16	−152.4 (2)	C4—C3—C2—C1	−0.2 (2)
N4—C18—C17—C16	26.4 (3)	C9—C8—C13—C12	0.4 (4)
O1—C5—N2—C6	−6.0 (3)	C7—C8—C13—C12	179.6 (2)
C4—C5—N2—C6	171.8 (2)	C21—C22—C23—C24	−0.4 (4)
C1—N1—C7—C8	75.4 (2)	C12—C11—C10—C9	0.3 (4)
C4—N1—C7—C8	−93.1 (2)	C8—C9—C10—C11	−0.6 (4)
N3—C17—C16—C15	0.5 (2)	C10—C11—C12—C13	0.4 (4)
C18—C17—C16—C15	172.66 (19)	C8—C13—C12—C11	−0.7 (4)
C17—C16—C15—C14	0.3 (2)	C26—C25—C24—C23	−0.7 (4)
N1—C7—C8—C13	17.1 (3)	C22—C23—C24—C25	0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O1i	0.87 (3)	2.04 (3)	2.869 (2)	161 (3)
N2—H2A···O3ii	0.86 (4)	2.10 (4)	2.902 (2)	154 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O1i	0.87 (3)	2.04 (3)	2.869 (2)	161 (3)
N2—H2A⋯O3ii	0.86 (4)	2.10 (4)	2.902 (2)	154 (3)

Symmetry codes: (i) ; (ii) .