Crystal structure of 4-amino-benzoic acid-4-methyl-pyridine (1/1).

In the title 1:1 adduct, C6H7N·C7H7NO2, the carb-oxy-lic acid group is twisted at an angle of 4.32 (18)° with respect to the attached benzene ring. In the crystal, the carb-oxy-lic acid group is linked to the pyridine ring by an O-H⋯N hydrogen bond, forming a dimer. The dimers are linked by N-H⋯O hydrogen bonds, generating (010) sheets.

Related literature

For background to pyridine derivatives, see: Tomaru et al. (1991 ▸). Katritzky et al. (1996 ▸); Akkurt et al. (2005 ▸). For related structures, see: Smith & Wermuth (2010 ▸); Hemamalini & Fun (2010 ▸); Kannan et al. (2012 ▸); Thanigaimani et al. (2012 ▸); Muralidharan et al. (2013 ▸).

Experimental

Crystal data

C6H7N·C7H7NO2

M = 230.26

Monoclinic,

a = 7.5970 (7) Å

b = 11.6665 (12) Å

c = 7.6754 (8) Å

β = 114.200 (3)°

V = 620.49 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 295 K

0.28 × 0.24 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▸) T min = 0.977, T max = 0.983

10064 measured reflections

2144 independent reflections

1458 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.108

S = 1.03

2144 reflections

159 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: SAINT (Bruker, 2004 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2015 ▸); molecular graphics: PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015000791/hb7348sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015000791/hb7348Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S2056989015000791/hb7348fig1.tif

The mol­ecular structure of (I), with 30% probability displacement ellipsoids for non-H atoms.

CCDC reference: 1043592

Additional supporting information: crystallographic information; 3D view; checkCIF report

C6H7N·C7H7NO2	F(000) = 244
Mr = 230.26	Dx = 1.232 Mg m−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 2749 reflections
a = 7.5970 (7) Å	θ = 3.4–21.8°
b = 11.6665 (12) Å	µ = 0.09 mm−1
c = 7.6754 (8) Å	T = 295 K
β = 114.200 (3)°	Block, colourless
V = 620.49 (11) Å3	0.28 × 0.24 × 0.20 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	2144 independent reflections
Radiation source: fine-focus sealed tube	1458 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω and φ scan	θmax = 26.7°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
Tmin = 0.977, Tmax = 0.983	k = −14→14
10064 measured reflections	l = −9→9

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.0554P)2 + 0.0229P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2144 reflections	Δρmax = 0.12 e Å−3
159 parameters	Δρmin = −0.13 e Å−3
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (4)

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.

	x	y	z	Uiso*/Ueq
C1	0.3693 (4)	0.1034 (2)	0.7149 (4)	0.0567 (6)
C2	0.4434 (4)	0.2029 (2)	0.6722 (4)	0.0591 (7)
H2	0.3671	0.2471	0.5675	0.071*
C3	0.6273 (4)	0.2362 (2)	0.7829 (3)	0.0558 (6)
H3	0.6737	0.3037	0.7529	0.067*
C4	0.7475 (4)	0.1730 (2)	0.9383 (4)	0.0508 (6)
C5	0.6737 (4)	0.0738 (2)	0.9798 (4)	0.0594 (7)
H5	0.7516	0.0294	1.0835	0.071*
C6	0.4892 (4)	0.0392 (2)	0.8724 (4)	0.0629 (7)
H6	0.4429	−0.0278	0.9043	0.076*
C7	0.9416 (4)	0.2104 (2)	1.0596 (4)	0.0587 (7)
C8	0.4371 (5)	0.4546 (2)	1.3188 (5)	0.0729 (8)
H8	0.3567	0.5148	1.3183	0.087*
C9	0.6306 (4)	0.4655 (2)	1.4263 (4)	0.0693 (8)
H9	0.6791	0.5319	1.4967	0.083*
C10	0.7534 (4)	0.3784 (2)	1.4304 (4)	0.0639 (7)
C11	0.6716 (4)	0.2836 (2)	1.3242 (4)	0.0718 (8)
H11	0.7487	0.2220	1.3229	0.086*
C12	0.4767 (5)	0.2790 (3)	1.2196 (4)	0.0766 (9)
H12	0.4249	0.2135	1.1479	0.092*
C13	0.9658 (5)	0.3866 (3)	1.5468 (6)	0.0954 (11)
H13A	1.0310	0.3941	1.4635	0.143*
H13B	1.0099	0.3186	1.6229	0.143*
H13C	0.9930	0.4524	1.6289	0.143*
N1	0.1840 (4)	0.0710 (2)	0.6087 (4)	0.0827 (8)
H1A	0.1113	0.1124	0.5137	0.099*
H1B	0.1395	0.0092	0.6364	0.099*
N2	0.3582 (3)	0.3627 (2)	1.2152 (4)	0.0722 (6)
O1	0.9921 (3)	0.30989 (17)	1.0123 (3)	0.0808 (6)
H1	1.109 (2)	0.324 (3)	1.076 (5)	0.121*
O2	1.0516 (3)	0.15755 (17)	1.1996 (3)	0.0778 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0545 (16)	0.0584 (15)	0.0526 (15)	−0.0071 (14)	0.0173 (13)	−0.0070 (14)
C2	0.0599 (17)	0.0581 (15)	0.0489 (15)	0.0009 (12)	0.0118 (13)	0.0088 (12)
C3	0.0582 (16)	0.0536 (13)	0.0509 (15)	−0.0050 (13)	0.0175 (13)	0.0058 (12)
C4	0.0529 (14)	0.0490 (12)	0.0442 (13)	0.0040 (12)	0.0135 (12)	0.0026 (12)
C5	0.0671 (18)	0.0516 (14)	0.0484 (16)	0.0021 (13)	0.0124 (14)	0.0046 (12)
C6	0.077 (2)	0.0518 (14)	0.0590 (17)	−0.0076 (14)	0.0273 (15)	0.0048 (13)
C7	0.0563 (17)	0.0532 (13)	0.0583 (17)	0.0045 (13)	0.0150 (14)	0.0003 (14)
C8	0.0630 (18)	0.0626 (16)	0.081 (2)	0.0031 (15)	0.0172 (16)	0.0007 (16)
C9	0.068 (2)	0.0617 (17)	0.0665 (19)	−0.0085 (14)	0.0150 (16)	−0.0042 (13)
C10	0.0579 (18)	0.0740 (17)	0.0585 (17)	−0.0045 (16)	0.0225 (14)	0.0063 (15)
C11	0.0680 (19)	0.0723 (18)	0.078 (2)	0.0015 (15)	0.0325 (18)	−0.0048 (16)
C12	0.077 (2)	0.0747 (19)	0.074 (2)	−0.0158 (17)	0.0260 (17)	−0.0171 (16)
C13	0.0604 (19)	0.105 (2)	0.104 (3)	−0.0070 (17)	0.0163 (18)	0.002 (2)
N1	0.0655 (16)	0.0852 (18)	0.0809 (18)	−0.0163 (13)	0.0132 (14)	0.0063 (15)
N2	0.0567 (14)	0.0719 (15)	0.0766 (16)	−0.0059 (13)	0.0157 (12)	−0.0023 (13)
O1	0.0588 (11)	0.0691 (12)	0.0883 (16)	−0.0105 (10)	0.0035 (11)	0.0130 (11)
O2	0.0678 (13)	0.0726 (12)	0.0665 (12)	0.0068 (10)	0.0006 (10)	0.0090 (10)

C1—N1	1.359 (4)	C8—H8	0.9300
C1—C2	1.387 (3)	C9—C10	1.371 (4)
C1—C6	1.397 (4)	C9—H9	0.9300
C2—C3	1.361 (4)	C10—C11	1.363 (4)
C2—H2	0.9300	C10—C13	1.493 (5)
C3—C4	1.380 (3)	C11—C12	1.366 (4)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.379 (3)	C12—N2	1.319 (4)
C4—C7	1.452 (3)	C12—H12	0.9300
C5—C6	1.364 (4)	C13—H13A	0.9600
C5—H5	0.9300	C13—H13B	0.9600
C6—H6	0.9300	C13—H13C	0.9600
C7—O2	1.224 (3)	N1—H1A	0.8600
C7—O1	1.319 (3)	N1—H1B	0.8600
C8—N2	1.323 (3)	O1—H1	0.836 (10)
C8—C9	1.365 (4)
N1—C1—C2	120.8 (2)	C8—C9—C10	119.9 (3)
N1—C1—C6	121.2 (2)	C8—C9—H9	120.0
C2—C1—C6	118.0 (2)	C10—C9—H9	120.0
C3—C2—C1	120.2 (2)	C11—C10—C9	116.6 (3)
C3—C2—H2	119.9	C11—C10—C13	121.7 (3)
C1—C2—H2	119.9	C9—C10—C13	121.7 (3)
C2—C3—C4	122.2 (2)	C10—C11—C12	120.2 (3)
C2—C3—H3	118.9	C10—C11—H11	119.9
C4—C3—H3	118.9	C12—C11—H11	119.9
C5—C4—C3	117.4 (2)	N2—C12—C11	123.4 (3)
C5—C4—C7	120.4 (2)	N2—C12—H12	118.3
C3—C4—C7	122.1 (2)	C11—C12—H12	118.3
C6—C5—C4	121.5 (2)	C10—C13—H13A	109.5
C6—C5—H5	119.2	C10—C13—H13B	109.5
C4—C5—H5	119.2	H13A—C13—H13B	109.5
C5—C6—C1	120.6 (2)	C10—C13—H13C	109.5
C5—C6—H6	119.7	H13A—C13—H13C	109.5
C1—C6—H6	119.7	H13B—C13—H13C	109.5
O2—C7—O1	120.9 (3)	C1—N1—H1A	120.0
O2—C7—C4	124.1 (2)	C1—N1—H1B	120.0
O1—C7—C4	115.0 (2)	H1A—N1—H1B	120.0
N2—C8—C9	123.3 (3)	C12—N2—C8	116.6 (3)
N2—C8—H8	118.4	C7—O1—H1	112 (3)
C9—C8—H8	118.4
N1—C1—C2—C3	178.1 (3)	C3—C4—C7—O2	179.2 (3)
C6—C1—C2—C3	−0.5 (4)	C5—C4—C7—O1	−176.1 (2)
C1—C2—C3—C4	0.9 (4)	C3—C4—C7—O1	1.3 (3)
C2—C3—C4—C5	−0.5 (4)	N2—C8—C9—C10	0.0 (5)
C2—C3—C4—C7	−178.1 (2)	C8—C9—C10—C11	−0.2 (4)
C3—C4—C5—C6	−0.2 (4)	C8—C9—C10—C13	−179.7 (3)
C7—C4—C5—C6	177.4 (2)	C9—C10—C11—C12	0.4 (4)
C4—C5—C6—C1	0.5 (4)	C13—C10—C11—C12	179.9 (3)
N1—C1—C6—C5	−178.8 (3)	C10—C11—C12—N2	−0.4 (5)
C2—C1—C6—C5	−0.2 (4)	C11—C12—N2—C8	0.1 (5)
C5—C4—C7—O2	1.7 (4)	C9—C8—N2—C12	0.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2i	0.84 (1)	1.81 (1)	2.644 (3)	177 (4)
N1—H1A···O2ii	0.86	2.32	3.049 (3)	142
N1—H1B···O2iii	0.86	2.17	3.031 (3)	174

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1H1N2i	0.84(1)	1.81(1)	2.644(3)	177(4)
N1H1AO2ii	0.86	2.32	3.049(3)	142
N1H1BO2iii	0.86	2.17	3.031(3)	174

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