5-Carbamoyl-2-methyl-1-(2-methyl-benz-yl)pyridinium bromide.

In the title mol-ecular salt, C(15)H(17)N(2)O(+)·Br(-), the benzene and pyridinium rings form a dihedral angle of 83.0 (1)°. In the crystal, N-H⋯Br and N-H⋯O hydrogen bonds link the components into chains along [010]. These chains are linked by weak C-H⋯O and C-H⋯Br hydrogen bonds, forming a three-dimensional network.

Related literature

The title compound was prepared as an NAD+ (nicotinamide adenine dinucleotide) model. For the role of reduced nicotinamide co-factors (NADH and NADPH) in enzyme-catalysed reactions, see: Hollmann et al. (2001 ▶); Lee et al. (2011 ▶); Maenaka et al. (2012 ▶); Park et al. (2008 ▶); Ruppert et al. (1988 ▶); Zhu et al. (2003 ▶, 2006 ▶). For the generation of NADH, see: Qing et al. (2006 ▶). For an efficient method of in situ regeneration, see: Song et al. (2008 ▶). For a related structure, see: Kim et al. (2012 ▶).

Experimental

Crystal data

C15H17N2O+·Br−

M = 321.22

Monoclinic,

a = 8.4880 (17) Å

b = 10.502 (2) Å

c = 33.450 (7) Å

β = 96.85 (3)°

V = 2960.5 (10) Å3

Z = 8

Mo Kα radiation

μ = 2.77 mm−1

T = 293 K

0.50 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.338, T max = 0.769

8103 measured reflections

2879 independent reflections

1857 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.096

S = 1.00

2879 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.31 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: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Brandenburg, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812018958/lh5461sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018958/lh5461Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018958/lh5461Isup3.cml

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

C15H17N2O+·Br−	F(000) = 1312
Mr = 321.22	Dx = 1.441 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2248 reflections
a = 8.4880 (17) Å	θ = 2.3–25.2°
b = 10.502 (2) Å	µ = 2.77 mm−1
c = 33.450 (7) Å	T = 293 K
β = 96.85 (3)°	Block, colorless
V = 2960.5 (10) Å3	0.50 × 0.20 × 0.10 mm
Z = 8

Bruker SMART CCD diffractometer	2879 independent reflections
Radiation source: fine-focus sealed tube	1857 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
φ and ω scans	θmax = 26.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −9→10
Tmin = 0.338, Tmax = 0.769	k = −12→8
8103 measured reflections	l = −41→40

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0247P)2 + 1.3939P] where P = (Fo2 + 2Fc2)/3
2879 reflections	(Δ/σ)max = 0.001
174 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.31 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
Br1	0.01684 (4)	0.38708 (4)	0.349683 (12)	0.06234 (17)
N1	0.2074 (3)	0.3760 (3)	0.26330 (9)	0.0686 (9)
H1A	0.1599	0.4033	0.2830	0.082*
H1B	0.2111	0.2957	0.2585	0.082*
N2	0.4953 (3)	0.4466 (3)	0.15096 (8)	0.0435 (6)
O1	0.2735 (4)	0.5725 (3)	0.24558 (9)	0.0862 (9)
C1	0.2742 (4)	0.4572 (4)	0.24056 (11)	0.0577 (9)
C2	0.3589 (4)	0.4032 (3)	0.20721 (10)	0.0466 (8)
C3	0.3794 (4)	0.2738 (4)	0.20086 (11)	0.0590 (9)
H3	0.3414	0.2144	0.2180	0.071*
C4	0.4560 (4)	0.2342 (3)	0.16924 (11)	0.0570 (9)
H4	0.4696	0.1475	0.1652	0.068*
C5	0.5131 (4)	0.3198 (3)	0.14343 (10)	0.0468 (8)
C6	0.5919 (4)	0.2774 (3)	0.10809 (10)	0.0599 (10)
H6A	0.5354	0.3112	0.0838	0.090*
H6B	0.5916	0.1861	0.1068	0.090*
H6C	0.6993	0.3078	0.1109	0.090*
C7	0.4195 (3)	0.4868 (3)	0.18186 (9)	0.0452 (8)
H7	0.4083	0.5737	0.1860	0.054*
C8	0.5564 (4)	0.5431 (3)	0.12466 (10)	0.0503 (9)
H8A	0.6635	0.5199	0.1201	0.060*
H8B	0.5617	0.6246	0.1384	0.060*
C9	0.4566 (4)	0.5572 (3)	0.08456 (10)	0.0500 (9)
C10	0.3025 (4)	0.5121 (3)	0.07804 (11)	0.0609 (10)
H10	0.2579	0.4712	0.0986	0.073*
C11	0.2144 (5)	0.5281 (4)	0.04038 (14)	0.0816 (13)
H11	0.1113	0.4971	0.0356	0.098*
C12	0.2825 (7)	0.5909 (4)	0.01029 (14)	0.0939 (17)
H12	0.2248	0.6027	−0.0149	0.113*
C13	0.4333 (7)	0.6351 (4)	0.01754 (14)	0.0880 (14)
H13	0.4773	0.6767	−0.0030	0.106*
C14	0.5231 (5)	0.6206 (3)	0.05406 (12)	0.0664 (11)
C15	0.6904 (6)	0.6707 (5)	0.06056 (15)	0.1029 (16)
H15A	0.7139	0.7144	0.0368	0.154*
H15B	0.7629	0.6010	0.0661	0.154*
H15C	0.7010	0.7286	0.0829	0.154*

	U11	U22	U33	U12	U13	U23
Br1	0.0576 (3)	0.0523 (3)	0.0775 (3)	−0.0027 (2)	0.00950 (18)	0.0134 (2)
N1	0.075 (2)	0.078 (2)	0.0571 (19)	−0.0028 (19)	0.0258 (17)	−0.0019 (17)
N2	0.0468 (15)	0.0348 (15)	0.0494 (16)	0.0015 (13)	0.0076 (13)	−0.0034 (13)
O1	0.118 (2)	0.0592 (18)	0.091 (2)	0.0093 (18)	0.0527 (18)	−0.0127 (16)
C1	0.057 (2)	0.065 (3)	0.052 (2)	0.007 (2)	0.0107 (18)	−0.001 (2)
C2	0.0435 (18)	0.051 (2)	0.0451 (19)	0.0017 (16)	0.0045 (15)	−0.0026 (17)
C3	0.071 (2)	0.045 (2)	0.061 (2)	−0.0051 (19)	0.011 (2)	0.0024 (18)
C4	0.072 (2)	0.035 (2)	0.065 (2)	0.0027 (18)	0.0104 (19)	−0.0033 (18)
C5	0.0427 (19)	0.037 (2)	0.059 (2)	0.0023 (16)	0.0002 (16)	−0.0075 (17)
C6	0.057 (2)	0.053 (2)	0.071 (2)	0.0049 (18)	0.0164 (19)	−0.0177 (19)
C7	0.0461 (19)	0.044 (2)	0.0453 (19)	0.0041 (16)	0.0042 (16)	−0.0068 (16)
C8	0.057 (2)	0.038 (2)	0.058 (2)	−0.0058 (17)	0.0144 (18)	−0.0061 (17)
C9	0.064 (2)	0.0372 (19)	0.050 (2)	0.0100 (18)	0.0107 (18)	−0.0060 (17)
C10	0.065 (2)	0.054 (2)	0.062 (3)	0.018 (2)	0.001 (2)	−0.0070 (19)
C11	0.078 (3)	0.073 (3)	0.090 (3)	0.029 (2)	−0.008 (3)	−0.021 (3)
C12	0.142 (5)	0.079 (4)	0.055 (3)	0.046 (3)	−0.014 (3)	0.002 (2)
C13	0.129 (4)	0.071 (3)	0.064 (3)	0.014 (3)	0.013 (3)	0.004 (2)
C14	0.103 (3)	0.042 (2)	0.055 (2)	0.007 (2)	0.014 (2)	−0.0017 (19)
C15	0.137 (4)	0.088 (3)	0.092 (3)	−0.044 (3)	0.048 (3)	0.005 (3)

N1—C1	1.315 (5)	C7—H7	0.9300
N1—H1A	0.8600	C8—C9	1.506 (5)
N1—H1B	0.8600	C8—H8A	0.9700
N2—C7	1.348 (4)	C8—H8B	0.9700
N2—C5	1.367 (4)	C9—C10	1.384 (5)
N2—C8	1.476 (4)	C9—C14	1.393 (5)
O1—C1	1.224 (4)	C10—C11	1.397 (5)
C1—C2	1.508 (5)	C10—H10	0.9300
C2—C7	1.363 (4)	C11—C12	1.385 (7)
C2—C3	1.390 (5)	C11—H11	0.9300
C3—C4	1.371 (5)	C12—C13	1.357 (7)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.374 (5)	C13—C14	1.369 (6)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.494 (4)	C14—C15	1.505 (6)
C6—H6A	0.9600	C15—H15A	0.9600
C6—H6B	0.9600	C15—H15B	0.9600
C6—H6C	0.9600	C15—H15C	0.9600
C1—N1—H1A	120.0	N2—C8—C9	113.5 (3)
C1—N1—H1B	120.0	N2—C8—H8A	108.9
H1A—N1—H1B	120.0	C9—C8—H8A	108.9
C7—N2—C5	121.3 (3)	N2—C8—H8B	108.9
C7—N2—C8	118.4 (3)	C9—C8—H8B	108.9
C5—N2—C8	120.3 (3)	H8A—C8—H8B	107.7
O1—C1—N1	123.6 (4)	C10—C9—C14	120.4 (3)
O1—C1—C2	118.9 (4)	C10—C9—C8	121.8 (3)
N1—C1—C2	117.5 (3)	C14—C9—C8	117.7 (3)
C7—C2—C3	118.1 (3)	C9—C10—C11	119.7 (4)
C7—C2—C1	117.9 (3)	C9—C10—H10	120.2
C3—C2—C1	124.0 (3)	C11—C10—H10	120.2
C4—C3—C2	119.6 (3)	C12—C11—C10	119.2 (4)
C4—C3—H3	120.2	C12—C11—H11	120.4
C2—C3—H3	120.2	C10—C11—H11	120.4
C3—C4—C5	121.4 (3)	C13—C12—C11	120.0 (4)
C3—C4—H4	119.3	C13—C12—H12	120.0
C5—C4—H4	119.3	C11—C12—H12	120.0
N2—C5—C4	117.8 (3)	C12—C13—C14	122.3 (5)
N2—C5—C6	120.4 (3)	C12—C13—H13	118.8
C4—C5—C6	121.8 (3)	C14—C13—H13	118.8
C5—C6—H6A	109.5	C13—C14—C9	118.4 (4)
C5—C6—H6B	109.5	C13—C14—C15	120.3 (4)
H6A—C6—H6B	109.5	C9—C14—C15	121.3 (4)
C5—C6—H6C	109.5	C14—C15—H15A	109.5
H6A—C6—H6C	109.5	C14—C15—H15B	109.5
H6B—C6—H6C	109.5	H15A—C15—H15B	109.5
N2—C7—C2	121.7 (3)	C14—C15—H15C	109.5
N2—C7—H7	119.1	H15A—C15—H15C	109.5
C2—C7—H7	119.1	H15B—C15—H15C	109.5
O1—C1—C2—C7	−5.5 (5)	C1—C2—C7—N2	−179.2 (3)
N1—C1—C2—C7	175.8 (3)	C7—N2—C8—C9	−103.9 (3)
O1—C1—C2—C3	174.2 (4)	C5—N2—C8—C9	74.9 (4)
N1—C1—C2—C3	−4.5 (5)	N2—C8—C9—C10	17.3 (4)
C7—C2—C3—C4	−1.4 (5)	N2—C8—C9—C14	−164.3 (3)
C1—C2—C3—C4	178.9 (3)	C14—C9—C10—C11	1.2 (5)
C2—C3—C4—C5	−0.1 (5)	C8—C9—C10—C11	179.6 (3)
C7—N2—C5—C4	−2.2 (4)	C9—C10—C11—C12	−0.9 (6)
C8—N2—C5—C4	179.0 (3)	C10—C11—C12—C13	0.4 (7)
C7—N2—C5—C6	177.6 (3)	C11—C12—C13—C14	−0.2 (7)
C8—N2—C5—C6	−1.1 (4)	C12—C13—C14—C9	0.5 (6)
C3—C4—C5—N2	1.9 (5)	C12—C13—C14—C15	179.6 (4)
C3—C4—C5—C6	−177.9 (3)	C10—C9—C14—C13	−1.0 (5)
C5—N2—C7—C2	0.8 (5)	C8—C9—C14—C13	−179.5 (3)
C8—N2—C7—C2	179.5 (3)	C10—C9—C14—C15	179.9 (4)
C3—C2—C7—N2	1.1 (5)	C8—C9—C14—C15	1.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Br1	0.86	2.67	3.477 (3)	157
N1—H1B···O1i	0.86	2.35	3.207 (4)	173
C3—H3···O1i	0.93	2.22	3.149 (5)	174
C4—H4···Br1i	0.93	2.78	3.712 (4)	175
C6—H6C···Br1ii	0.96	2.73	3.638 (3)	157
C8—H8B···Br1iii	0.97	2.87	3.782 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Br1	0.86	2.67	3.477 (3)	157
N1—H1B⋯O1i	0.86	2.35	3.207 (4)	173
C3—H3⋯O1i	0.93	2.22	3.149 (5)	174
C4—H4⋯Br1i	0.93	2.78	3.712 (4)	175
C6—H6C⋯Br1ii	0.96	2.73	3.638 (3)	157
C8—H8B⋯Br1iii	0.97	2.87	3.782 (3)	156

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