1-(3,5-Dimeth-oxy-benz-yl)-1H-pyrrole.

The title compound, C(13)H(15)NO(2), was synthesized from 3,5-dimeth-oxy-benzaldehyde. The dihedral angle between the pyrrole and benzene rings is 89.91 (5)°. In the crystal, weak C-H⋯O and C-H⋯π interactions link the mol-ecules into a three-dimensional network.

Related literature

For the anti-HIV-1 activity of N-(aryl­meth­yl)-pyrrole, see: Liu et al. (2008 ▶); Teixeira et al. (2008 ▶). For a related structure, see: Wang et al. (2011 ▶). For the synthesis of 3,5-dimeth­oxy-benzyl­amine, see: Yraola et al. (2006 ▶).

Experimental

Crystal data

C13H15NO2

M = 217.26

Monoclinic,

a = 9.7569 (11) Å

b = 12.2303 (10) Å

c = 10.4181 (10) Å

β = 113.720 (7)°

V = 1138.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 153 K

0.21 × 0.21 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

7643 measured reflections

2230 independent reflections

1717 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.140

S = 0.99

2230 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536812015024/rk2345sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015024/rk2345Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015024/rk2345Isup3.cml

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

C13H15NO2	F(000) = 464
Mr = 217.26	Dx = 1.268 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2351 reflections
a = 9.7569 (11) Å	θ = 2.8–26.0°
b = 12.2303 (10) Å	µ = 0.09 mm−1
c = 10.4181 (10) Å	T = 153 K
β = 113.720 (7)°	Needle, colorless
V = 1138.2 (2) Å3	0.21 × 0.21 × 0.16 mm
Z = 4

Bruker APEXII CCD diffractometer	1717 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 26.0°, θmin = 2.7°
φ and ω scans	h = −12→8
7643 measured reflections	k = −15→15
2230 independent reflections	l = −11→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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
2230 reflections	(Δ/σ)max = 0.014
145 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
N	0.14877 (13)	0.21993 (9)	0.87889 (11)	0.0396 (3)
O1	0.13871 (14)	0.44438 (8)	0.47582 (11)	0.0572 (4)
O2	0.08702 (13)	0.07035 (8)	0.30839 (10)	0.0536 (3)
C11	0.13905 (15)	0.11206 (11)	0.54195 (14)	0.0397 (4)
H11A	0.1407	0.0373	0.5591	0.048*
C7	0.16360 (16)	0.29689 (11)	0.62375 (14)	0.0407 (4)
H7A	0.1814	0.3469	0.6959	0.049*
C9	0.10819 (16)	0.26083 (11)	0.37960 (14)	0.0384 (4)
H9A	0.0884	0.2858	0.2895	0.046*
C5	0.19169 (18)	0.14323 (12)	0.79460 (15)	0.0478 (4)
H5A	0.1358	0.0759	0.7850	0.057*
H5B	0.2971	0.1261	0.8437	0.057*
C8	0.13589 (16)	0.33349 (11)	0.48959 (14)	0.0394 (4)
C10	0.11093 (15)	0.14936 (10)	0.40823 (14)	0.0381 (4)
C1	0.24214 (17)	0.29419 (12)	0.96984 (15)	0.0455 (4)
H1A	0.3453	0.2980	0.9977	0.055*
C6	0.16472 (15)	0.18558 (11)	0.65030 (14)	0.0380 (4)
C12	0.0972 (2)	0.48874 (13)	0.33928 (16)	0.0573 (5)
H12A	0.1015	0.5671	0.3448	0.086*
H12B	−0.0028	0.4662	0.2808	0.086*
H12C	0.1650	0.4629	0.3000	0.086*
C4	0.00631 (16)	0.24161 (13)	0.86324 (15)	0.0475 (4)
H4A	−0.0788	0.2035	0.8059	0.057*
C2	0.15797 (19)	0.36182 (13)	1.01276 (16)	0.0514 (4)
H2A	0.1932	0.4197	1.0754	0.062*
C3	0.00937 (18)	0.32851 (14)	0.94572 (16)	0.0528 (4)
H3A	−0.0726	0.3599	0.9556	0.063*
C13	0.0520 (2)	0.10539 (13)	0.16790 (15)	0.0537 (4)
H13A	0.0360	0.0427	0.1082	0.081*
H13B	0.1336	0.1478	0.1651	0.081*
H13C	−0.0370	0.1493	0.1359	0.081*

	U11	U22	U33	U12	U13	U23
N	0.0424 (7)	0.0461 (7)	0.0284 (6)	−0.0016 (5)	0.0122 (5)	0.0034 (5)
O1	0.0951 (9)	0.0343 (6)	0.0415 (6)	−0.0005 (5)	0.0266 (6)	0.0034 (4)
O2	0.0836 (8)	0.0395 (6)	0.0364 (6)	−0.0022 (5)	0.0230 (6)	−0.0046 (4)
C11	0.0453 (8)	0.0327 (7)	0.0388 (8)	0.0017 (6)	0.0146 (7)	0.0029 (6)
C7	0.0502 (9)	0.0380 (8)	0.0321 (8)	−0.0007 (6)	0.0146 (6)	−0.0032 (6)
C9	0.0433 (8)	0.0409 (8)	0.0304 (7)	0.0010 (6)	0.0142 (6)	0.0035 (6)
C5	0.0616 (10)	0.0434 (8)	0.0366 (8)	0.0042 (7)	0.0180 (7)	0.0038 (6)
C8	0.0473 (8)	0.0329 (7)	0.0387 (8)	0.0005 (6)	0.0180 (6)	0.0012 (6)
C10	0.0433 (8)	0.0362 (7)	0.0343 (7)	0.0005 (6)	0.0150 (6)	−0.0028 (6)
C1	0.0442 (8)	0.0564 (9)	0.0331 (8)	−0.0090 (7)	0.0126 (6)	0.0010 (7)
C6	0.0401 (8)	0.0393 (8)	0.0326 (7)	0.0021 (6)	0.0126 (6)	0.0025 (6)
C12	0.0857 (12)	0.0398 (8)	0.0516 (10)	0.0030 (8)	0.0332 (9)	0.0121 (7)
C4	0.0390 (8)	0.0630 (10)	0.0367 (8)	−0.0048 (7)	0.0114 (7)	0.0107 (7)
C2	0.0703 (11)	0.0494 (9)	0.0366 (8)	−0.0056 (8)	0.0237 (8)	−0.0016 (7)
C3	0.0556 (10)	0.0625 (10)	0.0472 (9)	0.0140 (8)	0.0278 (8)	0.0130 (8)
C13	0.0745 (11)	0.0525 (9)	0.0329 (8)	−0.0035 (8)	0.0203 (8)	−0.0068 (7)

N—C4	1.3589 (19)	C5—C6	1.5097 (19)
N—C1	1.3631 (18)	C5—H5A	0.9700
N—C5	1.4568 (18)	C5—H5B	0.9700
O1—C8	1.3652 (16)	C1—C2	1.362 (2)
O1—C12	1.4207 (17)	C1—H1A	0.9300
O2—C10	1.3693 (16)	C12—H12A	0.9600
O2—C13	1.4284 (17)	C12—H12B	0.9600
C11—C6	1.3849 (19)	C12—H12C	0.9600
C11—C10	1.3845 (19)	C4—C3	1.359 (2)
C11—H11A	0.9300	C4—H4A	0.9300
C7—C6	1.3883 (19)	C2—C3	1.393 (2)
C7—C8	1.3868 (19)	C2—H2A	0.9300
C7—H7A	0.9300	C3—H3A	0.9300
C9—C8	1.3880 (19)	C13—H13A	0.9600
C9—C10	1.3934 (19)	C13—H13B	0.9600
C9—H9A	0.9300	C13—H13C	0.9600
C4—N—C1	108.58 (13)	C2—C1—H1A	126.0
C4—N—C5	125.56 (13)	N—C1—H1A	126.0
C1—N—C5	125.05 (13)	C11—C6—C7	119.33 (13)
C8—O1—C12	118.35 (12)	C11—C6—C5	119.39 (12)
C10—O2—C13	117.65 (11)	C7—C6—C5	121.27 (13)
C6—C11—C10	120.26 (12)	O1—C12—H12A	109.5
C6—C11—H11A	119.9	O1—C12—H12B	109.5
C10—C11—H11A	119.9	H12A—C12—H12B	109.5
C6—C7—C8	120.00 (13)	O1—C12—H12C	109.5
C6—C7—H7A	120.0	H12A—C12—H12C	109.5
C8—C7—H7A	120.0	H12B—C12—H12C	109.5
C8—C9—C10	117.98 (12)	N—C4—C3	108.38 (13)
C8—C9—H9A	121.0	N—C4—H4A	125.8
C10—C9—H9A	121.0	C3—C4—H4A	125.8
N—C5—C6	113.71 (12)	C1—C2—C3	107.53 (15)
N—C5—H5A	108.8	C1—C2—H2A	126.2
C6—C5—H5A	108.8	C3—C2—H2A	126.2
N—C5—H5B	108.8	C4—C3—C2	107.42 (14)
C6—C5—H5B	108.8	C4—C3—H3A	126.3
H5A—C5—H5B	107.7	C2—C3—H3A	126.3
O1—C8—C7	115.00 (13)	O2—C13—H13A	109.5
O1—C8—C9	123.69 (13)	O2—C13—H13B	109.5
C7—C8—C9	121.31 (13)	H13A—C13—H13B	109.5
O2—C10—C11	115.85 (12)	O2—C13—H13C	109.5
O2—C10—C9	123.04 (12)	H13A—C13—H13C	109.5
C11—C10—C9	121.11 (13)	H13B—C13—H13C	109.5
C2—C1—N	108.07 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Cgi	0.93	2.79	3.6935 (19)	165
C2—H2A···O2ii	0.93	2.72	3.527 (2)	146
C5—H5A···O2iii	0.97	2.68	3.609 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C6–C11 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯Cgi	0.93	2.79	3.694 (2)	165
C2—H2A⋯O2ii	0.93	2.72	3.527 (2)	146
C5—H5A⋯O2iii	0.97	2.68	3.609 (2)	161

Symmetry codes: (i) ; (ii) ; (iii) .