2,2′-[(4-Bromo­phen­yl)methyl­ene]bis­(1H-pyrrole)

The title compound, C₁₅H₁₃BrN₂, is a substituted methane derivative. Three H atoms of the methane mol­ecule have been substituted by means of two pyrrole rings and one 4-bromo­phenyl moiety. The two pyrrole rings are inclined to one another by 85.0 (3)°, and to the benzene ring by 71.4 (2) and 69.5 (2)°. In the crystal, mol­ecules are linked via N—H...π and C—H...π inter­actions, forming layers parallel to (101). The layers are linked by C—Br...π inter­actions, forming a three-dimensional structure.

Key indicators

• Single-crystal X-ray study
• T = 299 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.063
• wR factor = 0.176
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full value Low .      0.947 Note

Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor       N1     --  H1N    ...     Please Check
PLAT420_ALERT_2_C D-H Without Acceptor       N2     --  H2N    ...     Please Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      5.848 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600        125 Report
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          1 Check

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT432_ALERT_2_G Short Inter X...Y Contact  Br1    ..  C14     ..       3.33 Ang.
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           2 Note
PLAT953_ALERT_1_G Reported (CIF) and Actual (FCF) Hmax Differ by .          1 Units
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density           1 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   7 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

2,2'-[(4-Bromophenyl)methylene]bis(1H-pyrrole)

Crystal data

C15H13BrN2	F(000) = 608
Mr = 301.18	Dx = 1.505 Mg m^−3
Monoclinic, P21/n	Melting point: 403 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 5.8132 (8) Å	Cell parameters from 1789 reflections
b = 19.763 (2) Å	θ = 2.7–27.8°
c = 11.656 (1) Å	µ = 3.08 mm^−1
β = 96.85 (1)°	T = 299 K
V = 1329.6 (3) Å^3	Prism, colourless
Z = 4	0.34 × 0.26 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2289 independent reflections
Radiation source: fine-focus sealed tube	1685 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Rotation method data acquisition using ω scans.	θmax = 25.4°, θmin = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −7→5
Tmin = 0.421, Tmax = 0.709	k = −23→17
4326 measured reflections	l = −12→13

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.176	H-atom parameters constrained
S = 1.20	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
2289 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.59 e Å^−3
0 restraints	Δρmin = −1.22 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br1	0.86594 (9)	0.49826 (2)	0.17591 (5)	0.0642 (3)
N1	0.7634 (6)	0.19396 (18)	−0.0868 (3)	0.0443 (9)
H1N	0.7680	0.2357	−0.1070	0.053*
N2	0.1873 (6)	0.14504 (19)	0.1458 (3)	0.0481 (9)
H2N	0.0954	0.1383	0.0834	0.058*
C1	0.4652 (6)	0.2148 (2)	0.0487 (3)	0.0355 (9)
H1	0.3273	0.2214	−0.0074	0.043*
C2	0.5648 (6)	0.28383 (19)	0.0784 (3)	0.0338 (9)
C3	0.4351 (7)	0.3416 (2)	0.0523 (4)	0.0417 (10)
H3	0.2867	0.3373	0.0133	0.050*
C4	0.5182 (7)	0.4049 (2)	0.0820 (4)	0.0432 (10)
H4	0.4270	0.4430	0.0642	0.052*
C5	0.7386 (7)	0.41107 (19)	0.1385 (3)	0.0395 (10)
C6	0.8724 (6)	0.3555 (2)	0.1673 (4)	0.0402 (10)
H6	1.0198	0.3603	0.2073	0.048*
C7	0.7871 (6)	0.29211 (19)	0.1364 (3)	0.0364 (9)
H7	0.8794	0.2543	0.1545	0.044*
C8	0.6299 (7)	0.1687 (2)	−0.0082 (3)	0.0387 (9)
C9	0.8879 (8)	0.1435 (3)	−0.1283 (4)	0.0541 (12)
H9	0.9927	0.1481	−0.1822	0.065*
C10	0.8336 (8)	0.0863 (3)	−0.0785 (4)	0.0620 (13)
H10	0.8927	0.0436	−0.0914	0.074*
C11	0.6677 (7)	0.1020 (2)	−0.0013 (4)	0.0500 (11)
H11	0.5990	0.0716	0.0451	0.060*
C12	0.3867 (6)	0.18121 (19)	0.1531 (3)	0.0351 (9)
C13	0.1542 (8)	0.1208 (2)	0.2525 (4)	0.0555 (12)
H13	0.0296	0.0948	0.2698	0.067*
C14	0.3335 (8)	0.1414 (2)	0.3281 (4)	0.0491 (11)
H14	0.3554	0.1322	0.4069	0.059*
C15	0.4810 (7)	0.1791 (2)	0.2662 (4)	0.0478 (11)
H15	0.6194	0.1992	0.2968	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0775 (5)	0.0397 (4)	0.0728 (5)	−0.0020 (2)	−0.0020 (3)	−0.0044 (2)
N1	0.048 (2)	0.059 (2)	0.028 (2)	−0.0062 (17)	0.0100 (16)	−0.0044 (16)
N2	0.039 (2)	0.059 (2)	0.045 (2)	−0.0109 (17)	0.0019 (17)	0.0040 (17)
C1	0.031 (2)	0.049 (2)	0.026 (2)	−0.0040 (17)	−0.0014 (16)	−0.0007 (17)
C2	0.033 (2)	0.047 (2)	0.022 (2)	−0.0015 (17)	0.0055 (16)	0.0024 (15)
C3	0.031 (2)	0.065 (3)	0.029 (2)	0.0060 (19)	0.0012 (18)	0.0050 (19)
C4	0.041 (2)	0.048 (3)	0.040 (3)	0.0109 (19)	0.0034 (19)	0.0049 (19)
C5	0.049 (2)	0.038 (2)	0.033 (2)	−0.0005 (18)	0.0112 (19)	−0.0012 (17)
C6	0.038 (2)	0.045 (3)	0.037 (2)	−0.0014 (18)	−0.0002 (19)	0.0006 (17)
C7	0.0279 (19)	0.043 (2)	0.038 (2)	0.0034 (17)	0.0009 (17)	0.0046 (17)
C8	0.037 (2)	0.053 (3)	0.025 (2)	−0.0065 (19)	0.0006 (16)	−0.0072 (18)
C9	0.049 (3)	0.078 (4)	0.036 (3)	−0.002 (2)	0.005 (2)	−0.014 (2)
C10	0.065 (3)	0.070 (4)	0.051 (3)	0.006 (3)	0.004 (2)	−0.021 (2)
C11	0.049 (3)	0.058 (3)	0.043 (3)	−0.004 (2)	0.007 (2)	−0.009 (2)
C12	0.031 (2)	0.040 (2)	0.035 (2)	−0.0054 (16)	0.0081 (17)	−0.0051 (16)
C13	0.052 (3)	0.055 (3)	0.065 (3)	−0.003 (2)	0.026 (2)	0.012 (2)
C14	0.063 (3)	0.051 (3)	0.037 (3)	0.001 (2)	0.017 (2)	0.0028 (19)
C15	0.046 (2)	0.069 (3)	0.029 (2)	−0.017 (2)	0.0059 (19)	−0.006 (2)

Geometric parameters (Å, º)

Br1—C5	1.905 (4)	C5—C6	1.365 (5)
N1—C9	1.355 (6)	C6—C7	1.379 (5)
N1—C8	1.364 (5)	C6—H6	0.9300
N1—H1N	0.8600	C7—H7	0.9300
N2—C12	1.356 (5)	C8—C11	1.336 (6)
N2—C13	1.368 (6)	C9—C10	1.326 (7)
N2—H2N	0.8600	C9—H9	0.9300
C1—C12	1.505 (5)	C10—C11	1.430 (6)
C1—C2	1.506 (5)	C10—H10	0.9300
C1—C8	1.529 (6)	C11—H11	0.9300
C1—H1	0.9800	C12—C15	1.366 (5)
C2—C3	1.381 (5)	C13—C14	1.344 (6)
C2—C7	1.395 (5)	C13—H13	0.9300
C3—C4	1.372 (6)	C14—C15	1.400 (5)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.374 (6)	C15—H15	0.9300
C4—H4	0.9300
C9—N1—C8	110.0 (4)	C6—C7—C2	121.1 (4)
C9—N1—H1N	125.0	C6—C7—H7	119.4
C8—N1—H1N	125.0	C2—C7—H7	119.4
C12—N2—C13	109.8 (4)	C11—C8—N1	107.4 (4)
C12—N2—H2N	125.1	C11—C8—C1	131.9 (4)
C13—N2—H2N	125.1	N1—C8—C1	120.6 (4)
C12—C1—C2	111.0 (3)	C10—C9—N1	107.8 (4)
C12—C1—C8	110.7 (3)	C10—C9—H9	126.1
C2—C1—C8	113.4 (3)	N1—C9—H9	126.1
C12—C1—H1	107.1	C9—C10—C11	107.7 (4)
C2—C1—H1	107.1	C9—C10—H10	126.2
C8—C1—H1	107.1	C11—C10—H10	126.2
C3—C2—C7	117.4 (4)	C8—C11—C10	107.2 (4)
C3—C2—C1	120.8 (3)	C8—C11—H11	126.4
C7—C2—C1	121.8 (3)	C10—C11—H11	126.4
C4—C3—C2	122.1 (4)	N2—C12—C15	106.6 (4)
C4—C3—H3	118.9	N2—C12—C1	121.4 (3)
C2—C3—H3	118.9	C15—C12—C1	132.0 (3)
C3—C4—C5	118.8 (4)	C14—C13—N2	107.9 (4)
C3—C4—H4	120.6	C14—C13—H13	126.0
C5—C4—H4	120.6	N2—C13—H13	126.0
C6—C5—C4	121.2 (4)	C13—C14—C15	107.4 (4)
C6—C5—Br1	118.5 (3)	C13—C14—H14	126.3
C4—C5—Br1	120.3 (3)	C15—C14—H14	126.3
C5—C6—C7	119.4 (4)	C12—C15—C14	108.3 (4)
C5—C6—H6	120.3	C12—C15—H15	125.9
C7—C6—H6	120.3	C14—C15—H15	125.9
C12—C1—C2—C3	−100.7 (4)	C12—C1—C8—N1	−164.7 (3)
C8—C1—C2—C3	133.9 (4)	C2—C1—C8—N1	−39.2 (5)
C12—C1—C2—C7	77.2 (4)	C8—N1—C9—C10	0.8 (5)
C8—C1—C2—C7	−48.1 (5)	N1—C9—C10—C11	−0.4 (6)
C7—C2—C3—C4	−0.4 (5)	N1—C8—C11—C10	0.6 (5)
C1—C2—C3—C4	177.7 (4)	C1—C8—C11—C10	176.9 (4)
C2—C3—C4—C5	0.7 (6)	C9—C10—C11—C8	−0.1 (5)
C3—C4—C5—C6	−1.4 (6)	C13—N2—C12—C15	0.5 (5)
C3—C4—C5—Br1	177.4 (3)	C13—N2—C12—C1	−179.1 (4)
C4—C5—C6—C7	1.7 (6)	C2—C1—C12—N2	139.7 (4)
Br1—C5—C6—C7	−177.2 (3)	C8—C1—C12—N2	−93.5 (4)
C5—C6—C7—C2	−1.3 (6)	C2—C1—C12—C15	−39.8 (6)
C3—C2—C7—C6	0.7 (5)	C8—C1—C12—C15	87.0 (5)
C1—C2—C7—C6	−177.3 (3)	C12—N2—C13—C14	−0.3 (5)
C9—N1—C8—C11	−0.8 (5)	N2—C13—C14—C15	−0.1 (5)
C9—N1—C8—C1	−177.7 (4)	N2—C12—C15—C14	−0.6 (5)
C12—C1—C8—C11	19.3 (6)	C1—C12—C15—C14	179.0 (4)
C2—C1—C8—C11	144.8 (4)	C13—C14—C15—C12	0.4 (5)

Hydrogen-bond geometry (Å, º)

Cg1, Cg2 and Cg3 are the centroids of the N1/C8–C11, N2/C12–C15 and C2–C7 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···Cg1^i	0.86	2.43	3.262 (4)	163
C6—H6···Cg1^ii	0.93	2.89	3.656 (5)	141
C9—H9···Cg3^iii	0.93	2.71	3.590 (5)	159
C14—H14···Cg3^iv	0.93	2.79	3.564 (5)	142
C5—Br1···Cg2^v	1.91 (1)	3.70 (1)	5.595 (4)	171 (1)

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