(E)-5-Methyl-2-(2-methyl­styryl)­pyrrole

Evaporation of a di­chloro­methane solution of the title compound, C₁₄H₁₅N, yielded a tar from which single crystals were obtained by sublimation. The title compound consists of two essentially planar moieties that are oriented in a synperiplanar fashion with respect to each other. The geometrical parameters are in accordance with literature values.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.054
• wR factor = 0.186
• Data-to-parameter ratio = 16.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_420  Alert C D-H Without Acceptor       N(1)   -   H(1)              ?

General Notes



ABSTM_02  When printed, the submitted absorption T values will be replaced
          by the scaled T values. Since the ratio of scaled T's is
          identical to the ratio of reported T values, the scaling does
          not imply a change to the absorption corrections used in the
          study.
          Ratio of Tmax expected/reported      1.066
          Tmax scaled      0.996 Tmin scaled      0.951


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: SET4 and CELDIM in CAD-4 Software (Enraf-Nonius, 1989); data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: PLATON (Spek, 1990).

(E)-5-Methyl-2-(2-methylstyryl)pyrrole

Crystal data

C14H15N	F(000) = 424
Mr = 197.27	Dx = 1.156 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 15 reflections
a = 12.056 (2) Å	θ = 3.2–19.7°
b = 7.545 (1) Å	µ = 0.07 mm^−1
c = 12.62 (2) Å	T = 293 K
β = 99.04 (4)°	Plate, yellow
V = 1133.7 (18) Å^3	0.20 × 0.15 × 0.06 mm
Z = 4

Data collection

Enraf-Nonius CAD-4 diffractometer	774 reflections with I > 2σ(I)
Radiation source: X-ray tube	Rint = 0.053
Graphite monochromator	θmax = 26.3°, θmin = 2.2°
θ/2θ scans	h = −15→14
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
Tmin = 0.893, Tmax = 0.935	l = 0→15
2404 measured reflections	3 standard reflections every 120 min
2299 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.186	H-atom parameters constrained
S = 0.90	w = 1/[σ^2(Fo^2) + (0.08P)^2] where P = (Fo^2 + 2Fc^2)/3
2299 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.2419 (2)	0.5444 (4)	−0.1835 (2)	0.0521 (11)
C2	0.3098 (3)	0.5709 (5)	−0.0869 (3)	0.0477 (12)
C3	0.4101 (3)	0.6283 (5)	−0.1127 (3)	0.0580 (16)
C4	0.4028 (3)	0.6355 (5)	−0.2231 (3)	0.0568 (16)
C5	0.2969 (3)	0.5822 (5)	−0.2678 (3)	0.0497 (12)
C6	0.2417 (3)	0.5665 (6)	−0.3794 (3)	0.0708 (17)
C7	0.2739 (3)	0.5461 (5)	0.0137 (3)	0.0512 (14)
C8	0.1761 (3)	0.4801 (5)	0.0323 (3)	0.0524 (14)
C9	0.1405 (3)	0.4691 (5)	0.1386 (3)	0.0443 (12)
C10	0.1794 (3)	0.5916 (5)	0.2175 (3)	0.0553 (14)
C11	0.1493 (3)	0.5839 (6)	0.3177 (3)	0.0636 (17)
C12	0.0789 (3)	0.4530 (6)	0.3400 (3)	0.0622 (16)
C13	0.0372 (3)	0.3307 (5)	0.2624 (3)	0.0548 (16)
C14	0.0676 (3)	0.3364 (5)	0.1624 (3)	0.0489 (12)
C15	0.0255 (3)	0.1941 (5)	0.0833 (3)	0.0721 (17)
H1	0.17350	0.50848	−0.19026	0.0627*
H3	0.47321	0.65795	−0.06354	0.0695*
H4	0.45976	0.67025	−0.26047	0.0680*
H6A	0.18691	0.65900	−0.39510	0.1064*
H6B	0.29681	0.57703	−0.42634	0.1064*
H6C	0.20534	0.45331	−0.38993	0.1064*
H7	0.32437	0.57965	0.07377	0.0615*
H8	0.12662	0.43796	−0.02625	0.0625*
H10	0.22718	0.68140	0.20207	0.0665*
H11	0.17663	0.66698	0.36975	0.0765*
H12	0.05872	0.44581	0.40797	0.0747*
H13	−0.01206	0.24339	0.27836	0.0656*
H15A	−0.02876	0.12253	0.11165	0.1079*
H15B	−0.00893	0.24750	0.01716	0.1079*
H15C	0.08724	0.12120	0.07029	0.1079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0464 (16)	0.055 (2)	0.054 (2)	−0.0079 (16)	0.0053 (16)	0.0105 (17)
C2	0.043 (2)	0.044 (2)	0.055 (2)	−0.0010 (18)	0.0041 (18)	0.0012 (19)
C3	0.045 (2)	0.057 (3)	0.071 (3)	−0.001 (2)	0.0060 (19)	−0.009 (2)
C4	0.052 (2)	0.059 (3)	0.062 (3)	−0.004 (2)	0.0170 (19)	0.001 (2)
C5	0.054 (2)	0.041 (2)	0.055 (2)	0.0000 (19)	0.0112 (19)	0.0021 (19)
C6	0.074 (3)	0.079 (3)	0.060 (3)	−0.009 (2)	0.012 (2)	0.007 (2)
C7	0.052 (2)	0.048 (3)	0.052 (2)	0.000 (2)	0.0030 (18)	0.0011 (19)
C8	0.050 (2)	0.054 (3)	0.051 (2)	−0.0052 (19)	0.0008 (18)	−0.0021 (19)
C9	0.042 (2)	0.044 (2)	0.045 (2)	0.0023 (19)	0.0012 (17)	−0.0017 (18)
C10	0.050 (2)	0.053 (3)	0.062 (2)	−0.007 (2)	0.0064 (19)	−0.007 (2)
C11	0.060 (3)	0.072 (3)	0.058 (3)	−0.004 (2)	0.007 (2)	−0.011 (2)
C12	0.057 (2)	0.077 (3)	0.055 (3)	0.010 (2)	0.016 (2)	0.004 (2)
C13	0.046 (2)	0.058 (3)	0.060 (3)	0.002 (2)	0.0070 (19)	0.003 (2)
C14	0.045 (2)	0.044 (2)	0.057 (2)	−0.0009 (18)	0.0061 (18)	−0.0039 (19)
C15	0.070 (3)	0.064 (3)	0.084 (3)	−0.014 (2)	0.017 (2)	−0.009 (2)

Geometric parameters (Å, º)

N1—C2	1.372 (5)	C14—C15	1.499 (6)
N1—C5	1.368 (5)	C3—H3	0.9303
N1—H1	0.8606	C4—H4	0.9298
C2—C7	1.417 (6)	C6—H6A	0.9600
C2—C3	1.371 (6)	C6—H6B	0.9604
C3—C4	1.383 (6)	C6—H6C	0.9596
C4—C5	1.372 (6)	C7—H7	0.9295
C5—C6	1.465 (6)	C8—H8	0.9297
C7—C8	1.334 (6)	C10—H10	0.9295
C8—C9	1.474 (6)	C11—H11	0.9300
C9—C14	1.396 (6)	C12—H12	0.9292
C9—C10	1.385 (6)	C13—H13	0.9299
C10—C11	1.371 (6)	C15—H15A	0.9597
C11—C12	1.360 (6)	C15—H15B	0.9604
C12—C13	1.382 (6)	C15—H15C	0.9602
C13—C14	1.369 (6)
N1···H8	2.7176	H6C···C2^vii	2.9029
C2···H6C^i	2.9029	H6C···C3^vii	2.8224
C3···H6C^i	2.8224	H7···C10	2.7109
C4···H13^ii	3.0365	H7···H10	2.2760
C4···H15A^ii	3.0595	H7···C13^viii	3.0925
C7···H10	2.7261	H8···N1	2.7176
C8···H1	2.8121	H8···C15	2.7042
C8···H15B	2.8211	H8···H1	2.2922
C8···H15C	2.9785	H8···H15B	2.3059
C8···H11^iii	3.0939	H10···C7	2.7261
C8···H15B^iv	2.8775	H10···H7	2.2760
C10···H7	2.7109	H10···C13^viii	3.0231
C11···H4^v	2.9879	H10···C14^viii	3.0141
C13···H7^iii	3.0925	H11···C8^viii	3.0939
C13···H10^iii	3.0231	H13···H15A	2.2727
C13···H1^iv	2.8332	H13···C4^ix	3.0365
C14···H10^iii	3.0141	H15A···H13	2.2727
C15···H8	2.7042	H15A···C4^ix	3.0595
H1···C8	2.8121	H15A···H6B^ix	2.5695
H1···H8	2.2922	H15B···C8	2.8211
H1···C13^iv	2.8332	H15B···H8	2.3059
H4···C11^vi	2.9879	H15B···C8^iv	2.8775
H6B···H15C^i	2.4826	H15C···C8	2.9785
H6B···H15A^ii	2.5695	H15C···H6B^vii	2.4826
C2—N1—C5	111.5 (3)	C5—C4—H4	125.99
C5—N1—H1	124.22	C5—C6—H6A	109.49
C2—N1—H1	124.24	C5—C6—H6B	109.42
N1—C2—C7	123.6 (3)	C5—C6—H6C	109.50
N1—C2—C3	105.1 (3)	H6A—C6—H6B	109.44
C3—C2—C7	131.3 (4)	H6A—C6—H6C	109.51
C2—C3—C4	109.4 (3)	H6B—C6—H6C	109.48
C3—C4—C5	108.1 (3)	C2—C7—H7	116.23
C4—C5—C6	132.2 (4)	C8—C7—H7	116.20
N1—C5—C6	121.9 (3)	C7—C8—H8	117.53
N1—C5—C4	105.9 (3)	C9—C8—H8	117.51
C2—C7—C8	127.6 (4)	C9—C10—H10	119.12
C7—C8—C9	125.0 (3)	C11—C10—H10	119.13
C10—C9—C14	118.5 (3)	C10—C11—H11	120.49
C8—C9—C10	120.2 (3)	C12—C11—H11	120.44
C8—C9—C14	121.3 (3)	C11—C12—H12	119.72
C9—C10—C11	121.7 (4)	C13—C12—H12	119.77
C10—C11—C12	119.1 (4)	C12—C13—H13	119.56
C11—C12—C13	120.5 (4)	C14—C13—H13	119.64
C12—C13—C14	120.8 (4)	C14—C15—H15A	109.51
C13—C14—C15	118.7 (3)	C14—C15—H15B	109.46
C9—C14—C13	119.3 (3)	C14—C15—H15C	109.49
C9—C14—C15	122.0 (3)	H15A—C15—H15B	109.46
C2—C3—H3	125.24	H15A—C15—H15C	109.48
C4—C3—H3	125.32	H15B—C15—H15C	109.42
C3—C4—H4	125.93
C5—N1—C2—C3	0.4 (4)	C7—C8—C9—C10	29.1 (6)
C5—N1—C2—C7	178.4 (4)	C14—C9—C10—C11	0.9 (6)
C2—N1—C5—C4	−0.4 (4)	C8—C9—C14—C13	179.7 (3)
C2—N1—C5—C6	−179.2 (4)	C8—C9—C14—C15	2.6 (6)
N1—C2—C3—C4	−0.2 (4)	C8—C9—C10—C11	−179.1 (4)
C7—C2—C3—C4	−178.1 (4)	C10—C9—C14—C13	−0.3 (5)
C3—C2—C7—C8	−176.0 (4)	C10—C9—C14—C15	−177.3 (3)
N1—C2—C7—C8	6.5 (6)	C9—C10—C11—C12	−0.3 (6)
C2—C3—C4—C5	0.0 (5)	C10—C11—C12—C13	−0.8 (6)
C3—C4—C5—N1	0.2 (4)	C11—C12—C13—C14	1.4 (6)
C3—C4—C5—C6	178.8 (4)	C12—C13—C14—C9	−0.8 (6)
C2—C7—C8—C9	−175.5 (4)	C12—C13—C14—C15	176.3 (4)
C7—C8—C9—C14	−150.9 (4)

Symmetry codes: (i) −x+1/2, y+1/2, −z−1/2; (ii) x+1/2, −y+1/2, z−1/2; (iii) −x+1/2, y−1/2, −z+1/2; (iv) −x, −y+1, −z; (v) x−1/2, −y+3/2, z+1/2; (vi) x+1/2, −y+3/2, z−1/2; (vii) −x+1/2, y−1/2, −z−1/2; (viii) −x+1/2, y+1/2, −z+1/2; (ix) x−1/2, −y+1/2, z+1/2.