Ethyl 3,4-dimethyl-5-[(E)-(phenyl-imino)-meth-yl]-1H-pyrrole-2-carboxyl-ate.

In the title compound, C(16)H(18)N(2)O(2), the mol-ecule adopts an E conformation about the C=N double bond. The dihedral angle between the pyrrole and phenyl rings is 41.55 (8)°. In the crystal structure, pairs of inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers. In the dimer, the two pyrrole rings are almost coplanar and the two phenyl rings are parallel to each other.

Related literature

For the structure of 5-formyl-3,4-dimethyl-1H-pyrrole-2-carboxyl­ate, see Wu et al. (2009 ▶). For the similar structure of ethyl 5-[(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyra­zol-4-yl)imino­meth­yl]-3,4-dimethyl-1H-pyrrole-2-carboxyl­ate, see Wang et al. (2009 ▶). For the coordination abilities for metal ions of pyrrol-2-yl­methyl­ene­amine ligands, see: Wang et al. (2010 ▶); Yang et al. (2003 ▶).

Experimental

Crystal data

C16H18N2O2

M = 270.32

Monoclinic,

a = 12.5463 (7) Å

b = 14.6525 (9) Å

c = 8.4490 (5) Å

β = 105.042 (3)°

V = 1500.00 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.35 × 0.26 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.975, T max = 0.986

12405 measured reflections

3413 independent reflections

2078 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.144

S = 1.01

3413 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810022051/gw2080sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022051/gw2080Isup2.hkl

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

C16H18N2O2	F(000) = 576
Mr = 270.32	Dx = 1.197 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5515 reflections
a = 12.5463 (7) Å	θ = 2.2–26.2°
b = 14.6525 (9) Å	µ = 0.08 mm−1
c = 8.4490 (5) Å	T = 296 K
β = 105.042 (3)°	Block, yellow
V = 1500.00 (15) Å3	0.35 × 0.26 × 0.18 mm
Z = 4

Bruker SMART CCD diffractometer	3413 independent reflections
Radiation source: fine-focus sealed tube	2078 reflections with I > 2σ(I)
graphite	Rint = 0.030
phi and ω scans	θmax = 27.6°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→16
Tmin = 0.975, Tmax = 0.986	k = −14→19
12405 measured reflections	l = −10→8

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: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0645P)2 + 0.3198P] where P = (Fo2 + 2Fc2)/3
3413 reflections	(Δ/σ)max = 0.007
184 parameters	Δρmax = 0.20 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
N2	0.02009 (11)	0.14614 (9)	0.03549 (16)	0.0474 (3)
H2A	−0.0130	0.0983	−0.0125	0.057*
O2	0.24807 (9)	0.06709 (8)	0.35169 (14)	0.0576 (3)
O3	0.12317 (10)	−0.01491 (9)	0.17093 (15)	0.0612 (4)
C14	0.15990 (13)	0.05888 (12)	0.22476 (19)	0.0462 (4)
C11	0.11351 (13)	0.14570 (11)	0.16129 (19)	0.0444 (4)
N1	−0.15004 (12)	0.33049 (10)	−0.16873 (18)	0.0545 (4)
C8	−0.01284 (13)	0.23366 (11)	−0.0027 (2)	0.0466 (4)
C10	0.14228 (13)	0.23604 (11)	0.20337 (19)	0.0458 (4)
C4	−0.25266 (15)	0.33933 (12)	−0.2860 (2)	0.0543 (5)
C7	−0.11212 (14)	0.25067 (12)	−0.1305 (2)	0.0514 (4)
H7	−0.1500	0.2012	−0.1874	0.062*
C9	0.06264 (13)	0.29161 (11)	0.1002 (2)	0.0465 (4)
C12	0.05849 (16)	0.39340 (12)	0.1001 (2)	0.0619 (5)
H12A	0.0308	0.4150	−0.0102	0.093*
H12B	0.1313	0.4172	0.1452	0.093*
H12C	0.0106	0.4135	0.1652	0.093*
C3	−0.26627 (17)	0.41010 (14)	−0.3976 (2)	0.0634 (5)
H3	−0.2072	0.4482	−0.3985	0.076*
C13	0.24063 (14)	0.26959 (13)	0.3311 (2)	0.0606 (5)
H13A	0.2367	0.3347	0.3399	0.091*
H13B	0.3067	0.2533	0.3006	0.091*
H13C	0.2416	0.2422	0.4347	0.091*
C2	−0.3674 (2)	0.42436 (17)	−0.5076 (3)	0.0782 (7)
H2	−0.3756	0.4714	−0.5838	0.094*
C15	0.29547 (16)	−0.01538 (14)	0.4354 (2)	0.0635 (5)
H15A	0.3295	−0.0515	0.3656	0.076*
H15B	0.2388	−0.0519	0.4644	0.076*
C16	0.37962 (17)	0.01386 (17)	0.5854 (3)	0.0793 (6)
H16A	0.4327	0.0528	0.5553	0.119*
H16B	0.4163	−0.0389	0.6416	0.119*
H16C	0.3442	0.0465	0.6562	0.119*
C5	−0.34233 (16)	0.28429 (15)	−0.2859 (3)	0.0727 (6)
H5	−0.3348	0.2364	−0.2116	0.087*
C1	−0.4555 (2)	0.37029 (19)	−0.5058 (3)	0.0869 (7)
H1	−0.5238	0.3809	−0.5789	0.104*
C6	−0.44248 (18)	0.30041 (18)	−0.3958 (3)	0.0893 (7)
H6	−0.5023	0.2631	−0.3950	0.107*

	U11	U22	U33	U12	U13	U23
N2	0.0494 (8)	0.0418 (8)	0.0461 (8)	0.0011 (6)	0.0038 (6)	−0.0006 (6)
O2	0.0557 (7)	0.0545 (8)	0.0523 (7)	0.0022 (6)	−0.0044 (6)	0.0051 (6)
O3	0.0666 (8)	0.0467 (8)	0.0594 (8)	0.0035 (6)	−0.0030 (6)	−0.0027 (6)
C14	0.0456 (9)	0.0511 (11)	0.0405 (9)	0.0002 (8)	0.0086 (7)	−0.0011 (7)
C11	0.0459 (9)	0.0457 (9)	0.0396 (9)	−0.0005 (7)	0.0075 (7)	0.0011 (7)
N1	0.0567 (9)	0.0494 (9)	0.0542 (9)	0.0074 (7)	0.0083 (7)	0.0051 (7)
C8	0.0506 (9)	0.0433 (9)	0.0460 (9)	0.0041 (7)	0.0128 (7)	0.0036 (7)
C10	0.0492 (9)	0.0479 (10)	0.0420 (9)	−0.0043 (7)	0.0149 (7)	−0.0020 (7)
C4	0.0579 (10)	0.0494 (10)	0.0528 (11)	0.0119 (8)	0.0092 (8)	0.0005 (8)
C7	0.0540 (10)	0.0481 (10)	0.0496 (10)	0.0036 (8)	0.0089 (8)	0.0022 (8)
C9	0.0512 (9)	0.0446 (9)	0.0465 (9)	−0.0008 (7)	0.0176 (8)	0.0013 (7)
C12	0.0680 (12)	0.0455 (10)	0.0714 (13)	−0.0028 (9)	0.0164 (10)	−0.0009 (9)
C3	0.0763 (13)	0.0590 (12)	0.0550 (11)	0.0166 (10)	0.0170 (10)	0.0081 (9)
C13	0.0593 (11)	0.0601 (12)	0.0583 (12)	−0.0110 (9)	0.0079 (9)	−0.0053 (9)
C2	0.0990 (17)	0.0783 (15)	0.0530 (12)	0.0344 (14)	0.0118 (12)	0.0095 (11)
C15	0.0636 (11)	0.0639 (12)	0.0568 (11)	0.0111 (9)	0.0046 (9)	0.0116 (9)
C16	0.0634 (12)	0.1025 (18)	0.0616 (13)	0.0050 (12)	−0.0025 (10)	0.0135 (12)
C5	0.0632 (12)	0.0629 (13)	0.0847 (15)	0.0045 (10)	0.0058 (11)	0.0142 (10)
C1	0.0742 (15)	0.0951 (19)	0.0755 (16)	0.0244 (14)	−0.0093 (12)	−0.0066 (13)
C6	0.0633 (13)	0.0848 (17)	0.106 (2)	0.0012 (12)	−0.0026 (13)	−0.0002 (15)

N2—C8	1.360 (2)	C12—H12C	0.9600
N2—C11	1.363 (2)	C3—C2	1.381 (3)
N2—H2A	0.8600	C3—H3	0.9300
O2—C14	1.3313 (18)	C13—H13A	0.9600
O2—C15	1.448 (2)	C13—H13B	0.9600
O3—C14	1.216 (2)	C13—H13C	0.9600
C14—C11	1.443 (2)	C2—C1	1.363 (3)
C11—C10	1.394 (2)	C2—H2	0.9300
N1—C7	1.272 (2)	C15—C16	1.487 (3)
N1—C4	1.412 (2)	C15—H15A	0.9700
C8—C9	1.395 (2)	C15—H15B	0.9700
C8—C7	1.443 (2)	C16—H16A	0.9600
C10—C9	1.403 (2)	C16—H16B	0.9600
C10—C13	1.496 (2)	C16—H16C	0.9600
C4—C3	1.382 (2)	C5—C6	1.375 (3)
C4—C5	1.384 (3)	C5—H5	0.9300
C7—H7	0.9300	C1—C6	1.364 (3)
C9—C12	1.492 (2)	C1—H1	0.9300
C12—H12A	0.9600	C6—H6	0.9300
C12—H12B	0.9600
C8—N2—C11	109.65 (13)	C4—C3—H3	119.9
C8—N2—H2A	125.2	C2—C3—H3	119.9
C11—N2—H2A	125.2	C10—C13—H13A	109.5
C14—O2—C15	117.92 (14)	C10—C13—H13B	109.5
O3—C14—O2	122.44 (15)	H13A—C13—H13B	109.5
O3—C14—C11	124.58 (15)	C10—C13—H13C	109.5
O2—C14—C11	112.98 (14)	H13A—C13—H13C	109.5
N2—C11—C10	107.94 (14)	H13B—C13—H13C	109.5
N2—C11—C14	118.44 (14)	C1—C2—C3	120.7 (2)
C10—C11—C14	133.60 (15)	C1—C2—H2	119.6
C7—N1—C4	118.36 (15)	C3—C2—H2	119.6
N2—C8—C9	108.10 (14)	O2—C15—C16	106.66 (17)
N2—C8—C7	119.37 (15)	O2—C15—H15A	110.4
C9—C8—C7	132.53 (16)	C16—C15—H15A	110.4
C11—C10—C9	107.29 (14)	O2—C15—H15B	110.4
C11—C10—C13	127.36 (15)	C16—C15—H15B	110.4
C9—C10—C13	125.34 (16)	H15A—C15—H15B	108.6
C3—C4—C5	118.75 (18)	C15—C16—H16A	109.5
C3—C4—N1	118.45 (17)	C15—C16—H16B	109.5
C5—C4—N1	122.62 (17)	H16A—C16—H16B	109.5
N1—C7—C8	122.82 (16)	C15—C16—H16C	109.5
N1—C7—H7	118.6	H16A—C16—H16C	109.5
C8—C7—H7	118.6	H16B—C16—H16C	109.5
C8—C9—C10	107.02 (14)	C6—C5—C4	120.0 (2)
C8—C9—C12	126.15 (15)	C6—C5—H5	120.0
C10—C9—C12	126.84 (15)	C4—C5—H5	120.0
C9—C12—H12A	109.5	C2—C1—C6	119.4 (2)
C9—C12—H12B	109.5	C2—C1—H1	120.3
H12A—C12—H12B	109.5	C6—C1—H1	120.3
C9—C12—H12C	109.5	C1—C6—C5	121.0 (2)
H12A—C12—H12C	109.5	C1—C6—H6	119.5
H12B—C12—H12C	109.5	C5—C6—H6	119.5
C4—C3—C2	120.1 (2)
C15—O2—C14—O3	−5.1 (2)	C9—C8—C7—N1	−1.8 (3)
C15—O2—C14—C11	174.30 (15)	N2—C8—C9—C10	−0.44 (18)
C8—N2—C11—C10	−0.93 (18)	C7—C8—C9—C10	178.79 (17)
C8—N2—C11—C14	177.75 (15)	N2—C8—C9—C12	179.75 (15)
O3—C14—C11—N2	2.1 (3)	C7—C8—C9—C12	−1.0 (3)
O2—C14—C11—N2	−177.28 (13)	C11—C10—C9—C8	−0.12 (18)
O3—C14—C11—C10	−179.64 (17)	C13—C10—C9—C8	178.52 (15)
O2—C14—C11—C10	1.0 (3)	C11—C10—C9—C12	179.69 (16)
C11—N2—C8—C9	0.85 (18)	C13—C10—C9—C12	−1.7 (3)
C11—N2—C8—C7	−178.50 (14)	C5—C4—C3—C2	−0.8 (3)
N2—C11—C10—C9	0.63 (18)	N1—C4—C3—C2	−176.03 (17)
C14—C11—C10—C9	−177.76 (18)	C4—C3—C2—C1	1.3 (3)
N2—C11—C10—C13	−177.97 (15)	C14—O2—C15—C16	−171.10 (15)
C14—C11—C10—C13	3.6 (3)	C3—C4—C5—C6	0.2 (3)
C7—N1—C4—C3	−141.86 (17)	N1—C4—C5—C6	175.21 (19)
C7—N1—C4—C5	43.1 (3)	C3—C2—C1—C6	−1.2 (3)
C4—N1—C7—C8	−174.75 (16)	C2—C1—C6—C5	0.6 (4)
N2—C8—C7—N1	177.38 (16)	C4—C5—C6—C1	−0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3i	0.86	2.06	2.8883 (18)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3i	0.86	2.06	2.8883 (18)	162

Symmetry code: (i) .