3-Carbamoyl-1-(2-nitrobenzyl)pyridin-ium bromide.

In the title compound, C(13)H(12)N(3)O(3) (+)·Br(-), the benzene and pyridinium rings form a dihedral angle of 82.0 (1)°. In the crystal, N-H⋯Br and N-H⋯O hydrogen bonds link the components into chains along [001]. In addition, weak C-H⋯O and C-H⋯Br hydrogen bonds are observed.

Related literature

The title compound was prepared as an NAD+ (nicotinamide adenine dinucleotide) model. For effective regeneration systems for co-enzymes (e.g. NADH), see: Hollmann et al. (2001 ▶); Lee et al. (2011 ▶); Maenaka et al. (2012 ▶); Park et al. (2008 ▶); Ruppert et al. (1988 ▶); Zhu et al. (2006 ▶). For the mechanisms of redox inter­conversions (NADH/NAD+), see: Zhu et al. (2003 ▶); Song et al. (2008 ▶).

Experimental

Crystal data

C13H12N3O3 +·Br−

M = 338.17

Monoclinic,

a = 17.576 (4) Å

b = 7.9990 (16) Å

c = 10.152 (2) Å

β = 105.88 (3)°

V = 1372.8 (5) Å3

Z = 4

Mo Kα radiation

μ = 3.01 mm−1

T = 293 K

0.15 × 0.15 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.661, T max = 0.753

7399 measured reflections

2684 independent reflections

2081 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.086

S = 1.04

2684 reflections

187 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.38 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 datablock(s) I, global. DOI: 10.1107/S1600536812015917/lh5450sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015917/lh5450Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015917/lh5450Isup3.cml

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

C13H12N3O3+·Br−	F(000) = 680
Mr = 338.17	Dx = 1.636 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11909 reflections
a = 17.576 (4) Å	θ = 2.7–27.6°
b = 7.9990 (16) Å	µ = 3.01 mm−1
c = 10.152 (2) Å	T = 293 K
β = 105.88 (3)°	Block, colorless
V = 1372.8 (5) Å3	0.15 × 0.15 × 0.10 mm
Z = 4

Bruker SMART CCD diffractometer	2684 independent reflections
Radiation source: fine-focus sealed tube	2081 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 26.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −21→21
Tmin = 0.661, Tmax = 0.753	k = −9→9
7399 measured reflections	l = −10→12

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0287P)2 + 0.3626P] where P = (Fo2 + 2Fc2)/3
2684 reflections	(Δ/σ)max = 0.001
187 parameters	Δρmax = 0.36 e Å−3
2 restraints	Δρmin = −0.38 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	0.299001 (18)	0.53711 (4)	0.36253 (3)	0.04487 (13)
N1	0.51901 (17)	0.2174 (4)	0.9902 (3)	0.0556 (7)
H1A	0.5634 (10)	0.181 (4)	1.041 (3)	0.067*
H1B	0.506 (2)	0.193 (5)	0.9045 (10)	0.067*
N2	0.09788 (14)	0.6339 (3)	1.1536 (2)	0.0374 (6)
N3	0.27770 (14)	0.5158 (3)	0.9346 (2)	0.0333 (5)
O1	0.48818 (12)	0.3289 (3)	1.1724 (2)	0.0515 (6)
O2	0.11894 (12)	0.7569 (3)	1.1007 (2)	0.0468 (5)
O3	0.06762 (15)	0.6449 (3)	1.2487 (3)	0.0648 (7)
C1	0.47318 (17)	0.3051 (4)	1.0485 (3)	0.0396 (7)
C2	0.40031 (16)	0.3825 (3)	0.9549 (3)	0.0330 (6)
C3	0.38718 (18)	0.3982 (4)	0.8142 (3)	0.0411 (7)
H3	0.4249	0.3592	0.7728	0.049*
C4	0.31891 (19)	0.4710 (4)	0.7355 (3)	0.0444 (8)
H4	0.3101	0.4811	0.6412	0.053*
C5	0.26429 (18)	0.5282 (4)	0.7981 (3)	0.0397 (7)
H5	0.2175	0.5760	0.7459	0.048*
C6	0.34414 (16)	0.4456 (3)	1.0136 (3)	0.0329 (6)
H6	0.3523	0.4396	1.1080	0.040*
C7	0.21733 (16)	0.5811 (3)	0.9988 (3)	0.0340 (7)
H7A	0.1859	0.6657	0.9398	0.041*
H7B	0.2436	0.6335	1.0854	0.041*
C8	0.16318 (15)	0.4428 (3)	1.0230 (3)	0.0298 (6)
C9	0.16802 (17)	0.2812 (4)	0.9765 (3)	0.0372 (7)
H9	0.2030	0.2585	0.9246	0.045*
C10	0.12235 (18)	0.1532 (4)	1.0052 (3)	0.0443 (8)
H10	0.1267	0.0464	0.9717	0.053*
C11	0.07044 (18)	0.1813 (4)	1.0828 (3)	0.0429 (7)
H11	0.0404	0.0941	1.1028	0.051*
C12	0.06342 (17)	0.3402 (4)	1.1305 (3)	0.0394 (7)
H12	0.0284	0.3615	1.1825	0.047*
C13	0.10931 (15)	0.4683 (3)	1.1001 (3)	0.0307 (6)

	U11	U22	U33	U12	U13	U23
Br1	0.0467 (2)	0.0500 (2)	0.0367 (2)	−0.00517 (15)	0.00936 (14)	0.00137 (15)
N1	0.0406 (17)	0.066 (2)	0.0561 (19)	0.0114 (15)	0.0063 (15)	−0.0072 (16)
N2	0.0361 (14)	0.0353 (15)	0.0415 (15)	0.0064 (11)	0.0120 (11)	−0.0022 (12)
N3	0.0364 (14)	0.0322 (13)	0.0346 (13)	−0.0001 (10)	0.0152 (11)	0.0025 (10)
O1	0.0402 (12)	0.0710 (16)	0.0435 (14)	0.0001 (11)	0.0117 (10)	0.0118 (12)
O2	0.0491 (13)	0.0332 (12)	0.0613 (15)	−0.0007 (10)	0.0202 (11)	−0.0023 (11)
O3	0.0894 (19)	0.0559 (16)	0.0689 (16)	0.0129 (13)	0.0549 (15)	−0.0026 (13)
C1	0.0320 (16)	0.0412 (18)	0.047 (2)	−0.0050 (13)	0.0134 (14)	0.0044 (15)
C2	0.0314 (15)	0.0317 (16)	0.0369 (16)	−0.0060 (12)	0.0111 (12)	0.0002 (13)
C3	0.0445 (18)	0.0419 (17)	0.0431 (18)	−0.0009 (14)	0.0224 (15)	−0.0049 (15)
C4	0.053 (2)	0.0526 (19)	0.0301 (16)	0.0042 (16)	0.0158 (14)	0.0022 (15)
C5	0.0418 (17)	0.0398 (17)	0.0348 (17)	0.0044 (14)	0.0056 (14)	0.0070 (14)
C6	0.0343 (15)	0.0359 (17)	0.0289 (15)	−0.0028 (13)	0.0092 (12)	0.0045 (12)
C7	0.0352 (16)	0.0331 (16)	0.0373 (16)	0.0037 (12)	0.0160 (13)	0.0013 (12)
C8	0.0278 (14)	0.0323 (16)	0.0274 (14)	0.0010 (11)	0.0044 (11)	0.0011 (12)
C9	0.0395 (16)	0.0374 (17)	0.0363 (17)	0.0032 (13)	0.0131 (13)	−0.0050 (13)
C10	0.0530 (19)	0.0298 (17)	0.0490 (19)	−0.0039 (14)	0.0121 (15)	−0.0054 (14)
C11	0.0438 (18)	0.0368 (18)	0.0486 (19)	−0.0129 (14)	0.0134 (15)	0.0015 (15)
C12	0.0330 (16)	0.0449 (19)	0.0425 (18)	−0.0027 (13)	0.0141 (13)	0.0028 (14)
C13	0.0307 (14)	0.0283 (14)	0.0320 (15)	−0.0001 (12)	0.0067 (12)	−0.0019 (12)

N1—C1	1.324 (4)	C4—H4	0.9300
N1—H1A	0.860 (2)	C5—H5	0.9300
N1—H1B	0.860 (2)	C6—H6	0.9300
N2—O2	1.226 (3)	C7—C8	1.523 (4)
N2—O3	1.227 (3)	C7—H7A	0.9700
N2—C13	1.466 (4)	C7—H7B	0.9700
N3—C5	1.344 (4)	C8—C9	1.387 (4)
N3—C6	1.345 (4)	C8—C13	1.398 (4)
N3—C7	1.484 (3)	C9—C10	1.381 (4)
O1—C1	1.227 (4)	C9—H9	0.9300
C1—C2	1.503 (4)	C10—C11	1.377 (4)
C2—C6	1.381 (4)	C10—H10	0.9300
C2—C3	1.389 (4)	C11—C12	1.377 (4)
C3—C4	1.376 (4)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.390 (4)
C4—C5	1.367 (4)	C12—H12	0.9300
C1—N1—H1A	119 (2)	C2—C6—H6	120.0
C1—N1—H1B	124 (3)	N3—C7—C8	111.6 (2)
H1A—N1—H1B	118 (4)	N3—C7—H7A	109.3
O2—N2—O3	122.4 (3)	C8—C7—H7A	109.3
O2—N2—C13	118.3 (2)	N3—C7—H7B	109.3
O3—N2—C13	119.3 (3)	C8—C7—H7B	109.3
C5—N3—C6	121.6 (2)	H7A—C7—H7B	108.0
C5—N3—C7	118.8 (2)	C9—C8—C13	116.1 (2)
C6—N3—C7	119.6 (2)	C9—C8—C7	121.5 (2)
O1—C1—N1	123.7 (3)	C13—C8—C7	122.2 (2)
O1—C1—C2	119.4 (3)	C10—C9—C8	121.8 (3)
N1—C1—C2	116.9 (3)	C10—C9—H9	119.1
C6—C2—C3	118.3 (3)	C8—C9—H9	119.1
C6—C2—C1	117.6 (3)	C11—C10—C9	120.9 (3)
C3—C2—C1	124.1 (3)	C11—C10—H10	119.5
C4—C3—C2	120.6 (3)	C9—C10—H10	119.5
C4—C3—H3	119.7	C10—C11—C12	119.3 (3)
C2—C3—H3	119.7	C10—C11—H11	120.4
C5—C4—C3	118.9 (3)	C12—C11—H11	120.4
C5—C4—H4	120.6	C11—C12—C13	119.3 (3)
C3—C4—H4	120.6	C11—C12—H12	120.4
N3—C5—C4	120.5 (3)	C13—C12—H12	120.4
N3—C5—H5	119.8	C12—C13—C8	122.6 (3)
C4—C5—H5	119.8	C12—C13—N2	115.9 (2)
N3—C6—C2	120.1 (3)	C8—C13—N2	121.4 (2)
N3—C6—H6	120.0
O1—C1—C2—C6	−14.2 (4)	N3—C7—C8—C13	170.4 (2)
N1—C1—C2—C6	167.5 (3)	C13—C8—C9—C10	−0.2 (4)
O1—C1—C2—C3	164.0 (3)	C7—C8—C9—C10	176.1 (3)
N1—C1—C2—C3	−14.3 (4)	C8—C9—C10—C11	−0.6 (5)
C6—C2—C3—C4	−1.7 (4)	C9—C10—C11—C12	0.9 (5)
C1—C2—C3—C4	−179.9 (3)	C10—C11—C12—C13	−0.5 (5)
C2—C3—C4—C5	0.2 (5)	C11—C12—C13—C8	−0.3 (4)
C6—N3—C5—C4	−0.8 (4)	C11—C12—C13—N2	179.5 (3)
C7—N3—C5—C4	179.3 (3)	C9—C8—C13—C12	0.7 (4)
C3—C4—C5—N3	1.0 (5)	C7—C8—C13—C12	−175.6 (3)
C5—N3—C6—C2	−0.7 (4)	C9—C8—C13—N2	−179.2 (2)
C7—N3—C6—C2	179.2 (2)	C7—C8—C13—N2	4.6 (4)
C3—C2—C6—N3	1.9 (4)	O2—N2—C13—C12	−160.2 (3)
C1—C2—C6—N3	−179.8 (2)	O3—N2—C13—C12	19.6 (4)
C5—N3—C7—C8	97.2 (3)	O2—N2—C13—C8	19.7 (4)
C6—N3—C7—C8	−82.7 (3)	O3—N2—C13—C8	−160.5 (3)
N3—C7—C8—C9	−5.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1i	0.86 (1)	2.30 (1)	3.143 (4)	168 (4)
N1—H1A···Br1ii	0.86 (1)	2.61 (1)	3.454 (3)	166 (3)
C4—H4···Br1	0.93	2.82	3.743 (3)	173
C7—H7B···Br1iii	0.97	2.82	3.595 (3)	137
C5—H5···O2iv	0.93	2.36	3.271 (4)	167
C3—H3···O1i	0.93	2.27	3.150 (4)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O1i	0.86 (1)	2.30 (1)	3.143 (4)	168 (4)
N1—H1A⋯Br1ii	0.86 (1)	2.61 (1)	3.454 (3)	166 (3)
C4—H4⋯Br1	0.93	2.82	3.743 (3)	173
C7—H7B⋯Br1iii	0.97	2.82	3.595 (3)	137
C5—H5⋯O2iv	0.93	2.36	3.271 (4)	167
C3—H3⋯O1i	0.93	2.27	3.150 (4)	157

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