Crystal structure and Hirshfeld surface analysis of a pyridiniminium bromide salt: 1-[2-([1,1′-biphen­yl]-4-yl)-2-oxoeth­yl]-3-methyl-1,4-di­hydro­pyridin-4-iminium bromide

The Br⁻ anion is linked to the cation by an N—H...Br hydrogen bond. C—H...O hydrogen bonds link adjacent pyridiniminium cations into inversion dimers with an (18) graph-set motif. These dimers are stacked in a phen­yl–phenyl T-shaped geometry through C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.030
• wR factor = 0.075
• Data-to-parameter ratio = 20.9

checkCIF/PLATON results

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Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.99 Report

Alert level G
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          2 Note
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2 Note
              Br
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         35 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         20 Info

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Computing details

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXL2013 (Sheldrick, 2015) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015) and PLATON (Spek, 2009).

1-[2-([1,1'-Biphenyl]-4-yl)-2-oxoethyl]-3-methyl-1,4-dihydropyridin-4-iminium bromide

Crystal data

C20H19N2O^+·Br^−	F(000) = 784
Mr = 383.28	Dx = 1.441 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 15.3991 (10) Å	Cell parameters from 7970 reflections
b = 7.9078 (5) Å	θ = 2.6–28.7°
c = 15.7645 (10) Å	µ = 2.34 mm^−1
β = 113.037 (1)°	T = 100 K
V = 1766.6 (2) Å^3	Plate, yellow
Z = 4	0.27 × 0.11 × 0.08 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer	4731 independent reflections
Radiation source: fine-focus sealed tube	3913 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
φ and ω scans	θmax = 29.2°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −20→21
Tmin = 0.499, Tmax = 0.574	k = −10→10
28949 measured reflections	l = −21→21

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.075	w = 1/[σ^2(Fo^2) + (0.0375P)^2 + 0.8608P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
4731 reflections	Δρmax = 0.70 e Å^−3
226 parameters	Δρmin = −0.23 e Å^−3

Special details

Experimental. The following wavelength and cell were deduced by SADABS from the direction cosines etc. They are given here for emergency use only: CELL 0.71093 15.443 7.924 15.800 89.974 113.042 90.030

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.

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

	x	y	z	Uiso*/Ueq
Br1	0.92732 (2)	1.53732 (2)	0.32391 (2)	0.02112 (6)
N1	0.85797 (10)	0.77203 (18)	0.52316 (10)	0.0165 (3)
N2	0.92877 (11)	1.25846 (19)	0.48455 (12)	0.0191 (3)
H1N2	0.9168 (16)	1.296 (3)	0.4320 (17)	0.028 (6)*
H2N2	0.9689 (16)	1.310 (3)	0.5315 (16)	0.026 (6)*
O1	0.68941 (9)	0.74507 (17)	0.53143 (11)	0.0288 (3)
C1	0.48304 (13)	−0.0147 (2)	0.60543 (12)	0.0190 (3)
H1A	0.4442	0.0614	0.5597	0.023*
C2	0.44287 (13)	−0.1546 (2)	0.62926 (12)	0.0217 (4)
H2A	0.3769	−0.1739	0.5993	0.026*
C3	0.49803 (13)	−0.2662 (2)	0.69624 (13)	0.0232 (4)
H3A	0.4703	−0.3613	0.7127	0.028*
C4	0.59455 (14)	−0.2375 (2)	0.73918 (13)	0.0241 (4)
H4A	0.6328	−0.3130	0.7856	0.029*
C5	0.63554 (13)	−0.0997 (2)	0.71483 (13)	0.0209 (4)
H5A	0.7018	−0.0830	0.7436	0.025*
C6	0.57967 (12)	0.0150 (2)	0.64790 (12)	0.0166 (3)
C7	0.62172 (12)	0.1671 (2)	0.62368 (11)	0.0160 (3)
C8	0.71004 (12)	0.1613 (2)	0.61812 (12)	0.0177 (3)
H8A	0.7449	0.0587	0.6312	0.021*
C9	0.74715 (12)	0.3039 (2)	0.59364 (12)	0.0176 (3)
H9A	0.8072	0.2981	0.5900	0.021*
C10	0.69697 (12)	0.4563 (2)	0.57416 (12)	0.0159 (3)
C11	0.60974 (12)	0.4633 (2)	0.58173 (12)	0.0173 (3)
H11A	0.5756	0.5667	0.5703	0.021*
C12	0.57262 (12)	0.3209 (2)	0.60576 (12)	0.0181 (3)
H12A	0.5129	0.3273	0.6102	0.022*
C13	0.73288 (12)	0.6126 (2)	0.54717 (12)	0.0174 (3)
C14	0.82786 (12)	0.6034 (2)	0.53803 (13)	0.0187 (3)
H14A	0.8757	0.5539	0.5948	0.022*
H14B	0.8224	0.5293	0.4856	0.022*
C15	0.83058 (12)	0.8351 (2)	0.43666 (12)	0.0178 (3)
H15A	0.7958	0.7642	0.3861	0.021*
C16	0.85084 (12)	0.9961 (2)	0.41921 (12)	0.0181 (3)
C17	0.90417 (11)	1.1006 (2)	0.49601 (12)	0.0160 (3)
C18	0.92986 (12)	1.0325 (2)	0.58534 (12)	0.0168 (3)
H18A	0.9638	1.0999	0.6378	0.020*
C19	0.90626 (12)	0.8711 (2)	0.59677 (12)	0.0175 (3)
H19A	0.9239	0.8270	0.6573	0.021*
C20	0.81947 (15)	1.0614 (3)	0.32252 (13)	0.0268 (4)
H20A	0.7890	0.9700	0.2790	0.040*
H20B	0.8743	1.1026	0.3118	0.040*
H20C	0.7745	1.1541	0.3135	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.02487 (10)	0.02019 (10)	0.01683 (9)	−0.00208 (7)	0.00658 (7)	0.00115 (7)
N1	0.0153 (7)	0.0152 (7)	0.0203 (7)	−0.0005 (5)	0.0083 (6)	−0.0004 (6)
N2	0.0222 (8)	0.0166 (7)	0.0195 (8)	−0.0018 (6)	0.0091 (6)	0.0010 (6)
O1	0.0230 (7)	0.0184 (6)	0.0487 (9)	0.0050 (5)	0.0179 (6)	0.0081 (6)
C1	0.0190 (8)	0.0230 (9)	0.0155 (8)	−0.0001 (7)	0.0072 (7)	0.0000 (7)
C2	0.0197 (9)	0.0271 (9)	0.0200 (9)	−0.0050 (7)	0.0097 (7)	−0.0031 (7)
C3	0.0284 (10)	0.0218 (9)	0.0233 (9)	−0.0050 (7)	0.0144 (8)	0.0009 (7)
C4	0.0272 (10)	0.0219 (9)	0.0245 (9)	0.0033 (7)	0.0116 (8)	0.0063 (7)
C5	0.0197 (8)	0.0205 (8)	0.0230 (9)	0.0004 (7)	0.0090 (7)	0.0026 (7)
C6	0.0193 (8)	0.0172 (8)	0.0155 (8)	−0.0003 (6)	0.0093 (7)	−0.0008 (6)
C7	0.0165 (8)	0.0174 (8)	0.0134 (8)	−0.0011 (6)	0.0052 (6)	0.0001 (6)
C8	0.0173 (8)	0.0158 (8)	0.0201 (8)	0.0011 (6)	0.0073 (7)	0.0006 (6)
C9	0.0163 (8)	0.0178 (8)	0.0204 (9)	0.0007 (6)	0.0089 (7)	−0.0007 (7)
C10	0.0160 (8)	0.0165 (8)	0.0145 (8)	−0.0005 (6)	0.0052 (6)	−0.0005 (6)
C11	0.0161 (8)	0.0164 (8)	0.0181 (8)	0.0030 (6)	0.0053 (6)	0.0011 (7)
C12	0.0147 (8)	0.0203 (8)	0.0198 (8)	0.0020 (6)	0.0072 (7)	0.0008 (7)
C13	0.0151 (8)	0.0162 (8)	0.0198 (8)	0.0005 (6)	0.0054 (7)	0.0011 (7)
C14	0.0189 (8)	0.0136 (7)	0.0248 (9)	0.0001 (6)	0.0096 (7)	0.0012 (7)
C15	0.0166 (8)	0.0196 (8)	0.0164 (8)	−0.0010 (6)	0.0056 (7)	−0.0014 (6)
C16	0.0145 (8)	0.0225 (9)	0.0171 (8)	0.0010 (6)	0.0059 (7)	0.0009 (6)
C17	0.0141 (8)	0.0163 (8)	0.0199 (8)	0.0019 (6)	0.0092 (7)	−0.0007 (7)
C18	0.0181 (8)	0.0183 (8)	0.0152 (8)	−0.0007 (7)	0.0078 (6)	−0.0023 (7)
C19	0.0179 (8)	0.0189 (8)	0.0178 (8)	0.0024 (6)	0.0093 (7)	0.0016 (7)
C20	0.0282 (10)	0.0311 (10)	0.0169 (9)	−0.0046 (8)	0.0044 (7)	0.0049 (8)

Geometric parameters (Å, º)

N1—C15	1.355 (2)	C8—H8A	0.9500
N1—C19	1.356 (2)	C9—C10	1.400 (2)
N1—C14	1.460 (2)	C9—H9A	0.9500
N2—C17	1.337 (2)	C10—C11	1.395 (2)
N2—H1N2	0.83 (2)	C10—C13	1.483 (2)
N2—H2N2	0.86 (2)	C11—C12	1.381 (2)
O1—C13	1.215 (2)	C11—H11A	0.9500
C1—C2	1.389 (3)	C12—H12A	0.9500
C1—C6	1.392 (2)	C13—C14	1.526 (2)
C1—H1A	0.9500	C14—H14A	0.9900
C2—C3	1.383 (3)	C14—H14B	0.9900
C2—H2A	0.9500	C15—C16	1.365 (2)
C3—C4	1.390 (3)	C15—H15A	0.9500
C3—H3A	0.9500	C16—C17	1.430 (2)
C4—C5	1.387 (3)	C16—C20	1.499 (3)
C4—H4A	0.9500	C17—C18	1.412 (2)
C5—C6	1.402 (2)	C18—C19	1.358 (2)
C5—H5A	0.9500	C18—H18A	0.9500
C6—C7	1.485 (2)	C19—H19A	0.9500
C7—C8	1.397 (2)	C20—H20A	0.9800
C7—C12	1.401 (2)	C20—H20B	0.9800
C8—C9	1.385 (2)	C20—H20C	0.9800
C15—N1—C19	119.94 (15)	C12—C11—C10	120.46 (16)
C15—N1—C14	120.28 (15)	C12—C11—H11A	119.8
C19—N1—C14	119.51 (15)	C10—C11—H11A	119.8
C17—N2—H1N2	120.3 (16)	C11—C12—C7	120.95 (16)
C17—N2—H2N2	118.3 (15)	C11—C12—H12A	119.5
H1N2—N2—H2N2	120 (2)	C7—C12—H12A	119.5
C2—C1—C6	120.64 (17)	O1—C13—C10	122.65 (16)
C2—C1—H1A	119.7	O1—C13—C14	119.56 (16)
C6—C1—H1A	119.7	C10—C13—C14	117.78 (15)
C3—C2—C1	120.60 (17)	N1—C14—C13	110.35 (14)
C3—C2—H2A	119.7	N1—C14—H14A	109.6
C1—C2—H2A	119.7	C13—C14—H14A	109.6
C2—C3—C4	119.21 (17)	N1—C14—H14B	109.6
C2—C3—H3A	120.4	C13—C14—H14B	109.6
C4—C3—H3A	120.4	H14A—C14—H14B	108.1
C5—C4—C3	120.62 (17)	N1—C15—C16	122.72 (16)
C5—C4—H4A	119.7	N1—C15—H15A	118.6
C3—C4—H4A	119.7	C16—C15—H15A	118.6
C4—C5—C6	120.33 (17)	C15—C16—C17	118.01 (16)
C4—C5—H5A	119.8	C15—C16—C20	121.21 (17)
C6—C5—H5A	119.8	C17—C16—C20	120.78 (16)
C1—C6—C5	118.57 (16)	N2—C17—C18	120.51 (16)
C1—C6—C7	120.31 (16)	N2—C17—C16	121.62 (16)
C5—C6—C7	121.11 (16)	C18—C17—C16	117.87 (16)
C8—C7—C12	118.53 (16)	C19—C18—C17	120.40 (16)
C8—C7—C6	121.51 (15)	C19—C18—H18A	119.8
C12—C7—C6	119.96 (15)	C17—C18—H18A	119.8
C9—C8—C7	120.55 (16)	N1—C19—C18	121.01 (16)
C9—C8—H8A	119.7	N1—C19—H19A	119.5
C7—C8—H8A	119.7	C18—C19—H19A	119.5
C8—C9—C10	120.64 (16)	C16—C20—H20A	109.5
C8—C9—H9A	119.7	C16—C20—H20B	109.5
C10—C9—H9A	119.7	H20A—C20—H20B	109.5
C11—C10—C9	118.85 (16)	C16—C20—H20C	109.5
C11—C10—C13	118.12 (15)	H20A—C20—H20C	109.5
C9—C10—C13	123.02 (16)	H20B—C20—H20C	109.5
C6—C1—C2—C3	0.6 (3)	C11—C10—C13—O1	−0.1 (3)
C1—C2—C3—C4	−0.5 (3)	C9—C10—C13—O1	−179.10 (18)
C2—C3—C4—C5	−0.6 (3)	C11—C10—C13—C14	−179.35 (16)
C3—C4—C5—C6	1.5 (3)	C9—C10—C13—C14	1.7 (2)
C2—C1—C6—C5	0.3 (3)	C15—N1—C14—C13	−87.86 (19)
C2—C1—C6—C7	−178.51 (16)	C19—N1—C14—C13	86.16 (18)
C4—C5—C6—C1	−1.4 (3)	O1—C13—C14—N1	8.2 (2)
C4—C5—C6—C7	177.47 (17)	C10—C13—C14—N1	−172.54 (14)
C1—C6—C7—C8	−142.49 (18)	C19—N1—C15—C16	1.1 (3)
C5—C6—C7—C8	38.7 (3)	C14—N1—C15—C16	175.11 (16)
C1—C6—C7—C12	37.5 (2)	N1—C15—C16—C17	0.7 (3)
C5—C6—C7—C12	−141.33 (18)	N1—C15—C16—C20	179.90 (17)
C12—C7—C8—C9	−1.2 (3)	C15—C16—C17—N2	178.41 (16)
C6—C7—C8—C9	178.73 (16)	C20—C16—C17—N2	−0.8 (3)
C7—C8—C9—C10	0.1 (3)	C15—C16—C17—C18	−2.1 (2)
C8—C9—C10—C11	1.4 (3)	C20—C16—C17—C18	178.76 (17)
C8—C9—C10—C13	−179.68 (16)	N2—C17—C18—C19	−178.81 (16)
C9—C10—C11—C12	−1.6 (3)	C16—C17—C18—C19	1.7 (2)
C13—C10—C11—C12	179.36 (16)	C15—N1—C19—C18	−1.6 (2)
C10—C11—C12—C7	0.5 (3)	C14—N1—C19—C18	−175.62 (15)
C8—C7—C12—C11	1.0 (3)	C17—C18—C19—N1	0.2 (3)
C6—C7—C12—C11	−179.00 (16)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···Br1	0.83 (2)	2.61 (2)	3.3514 (17)	150 (2)
N2—H2N2···Br1^i	0.86 (2)	2.52 (2)	3.3763 (17)	174 (2)
C1—H1A···O1^ii	0.95	2.52	3.431 (2)	162
C14—H14A···Br1^iii	0.99	2.88	3.710 (2)	141
C19—H19A···Br1^iv	0.95	2.82	3.5415 (18)	134
C3—H3A···Cg1^v	0.95	2.81	3.6963 (19)	155

Symmetry codes: (i) −x+2, −y+3, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+2, −y+2, −z+1; (iv) x, −y+5/2, z+1/2; (v) −x+1, y−1/2, −z+3/2.