Temperature-induced first-order displacive phase transition of isonicotinamide-4-methoxybenzoic acid co-crystal

Isonicotinamide–4-methoxybenzoic acid co-crystal (1), C₆H₆N₂O·C₈H₈O₃, is formed through slow evaporation from methanol solution and it undergoes a first-order isosymmetry (monoclinic I2/a ↔ monoclinic I2/a) structural phase transition at T_c = 142.5 (5) K, which has been confirmed by an abrupt jump of crystallographic interaxial angle β from variable-temperature single-crystal XRD and small heat hysteresis (6.25 K) in differential scanning calorimetry measurement. The three-dimensional X-ray crystal structures of (1) at the low-temperature phase (LTP) (100, 140 and 142 K) and the high-temperature phase (HTP) (143, 150, 200, 250 and 300 K) were solved and refined as a simple non-disordered model with final R[F² > 2σ(F²)] ≃ 0.05. The asymmetric unit of (1) consists of crystallographically independent 4-methoxybenzoic acid (A) and isonicotinamide (B) molecules in both enantiotropic phases. Molecule A adopts a `near-hydroxyl' conformation in which the hydroxyl and methoxy groups are positioned on the same side. Both `near-hydroxyl' and `near-carbonyl' molecular conformations possess minimum conformational energies with an energy difference of < 0.15 kJ mol⁻¹ from a potential energy surface scan. In the crystal, molecules are joined into linear ABBA arrays by intermolecular N—H...O and O—H...N hydrogen bonds which were preserved in both phases. However, these ABBA arrays are displaced from planarity upon LTP-to-HTP transition and the changes in inter-array interactions are observed in two-dimensional fingerprint plots of their Hirshfeld surfaces. The PIXEL energies of each molecular pair in both phases were calculated to investigate the difference in intermolecular interaction energies before and after the displacement of ABBA arrays from planarity, which directly leads to the single-crystal-to-single-crystal phase transition of (1).

Computing details

For all compounds, data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008), Mercury (Macrae, 2006); software used to prepare material for publication: PLATON (Spek, 2009).

(mo_in4meo2_0m) Isonicotinamide 4-methoxybenzoic acid

Crystal data

C8H8O3·C6H6N2O	F(000) = 1152
Mr = 274.27	Dx = 1.398 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 20.333 (2) Å	Cell parameters from 4328 reflections
b = 5.1356 (5) Å	θ = 2.6–28.3°
c = 24.966 (2) Å	µ = 0.10 mm^−1
β = 90.909 (6)°	T = 100 K
V = 2606.7 (4) Å^3	Plate, colourless
Z = 8	0.55 × 0.19 × 0.05 mm

Data collection

Bruker APEX Duo CCD area detector diffractometer	3212 independent reflections
Radiation source: fine-focus sealed tube	2619 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −26→26
Tmin = 0.899, Tmax = 0.970	k = −6→6
13967 measured reflections	l = −32→30

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0675P)^2 + 1.2363P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
3212 reflections	Δρmax = 0.37 e Å^−3
194 parameters	Δρmin = −0.21 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.

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

	x	y	z	Uiso*/Ueq
O1	0.99868 (4)	1.24213 (16)	0.54425 (3)	0.0183 (2)
O2	0.77882 (4)	0.16286 (16)	0.64553 (3)	0.0183 (2)
O3	0.70539 (4)	0.22808 (16)	0.57895 (3)	0.0185 (2)
O4	0.56123 (4)	−0.66208 (17)	0.70969 (3)	0.0209 (2)
N1	0.83993 (5)	0.56083 (19)	0.59967 (4)	0.0175 (2)
N2	0.91705 (5)	1.32472 (19)	0.48424 (4)	0.0162 (2)
C1	0.93334 (6)	0.8427 (2)	0.59283 (5)	0.0187 (2)
H1A	0.9756	0.8924	0.6060	0.022*
C2	0.89927 (6)	0.6406 (2)	0.61675 (5)	0.0201 (3)
H2A	0.9190	0.5549	0.6466	0.024*
C3	0.81249 (6)	0.6854 (2)	0.55783 (5)	0.0183 (2)
H3A	0.7703	0.6306	0.5454	0.022*
C4	0.84284 (5)	0.8914 (2)	0.53165 (5)	0.0171 (2)
H4A	0.8216	0.9755	0.5022	0.021*
C5	0.90470 (5)	0.9714 (2)	0.54940 (4)	0.0144 (2)
C6	0.94369 (5)	1.1914 (2)	0.52493 (4)	0.0143 (2)
C7	0.68311 (5)	−0.1004 (2)	0.64401 (4)	0.0153 (2)
C8	0.70751 (6)	−0.2547 (2)	0.68563 (5)	0.0173 (2)
H8A	0.7513	−0.2288	0.6984	0.021*
C9	0.66862 (5)	−0.4474 (2)	0.70886 (5)	0.0180 (2)
H9A	0.6856	−0.5516	0.7373	0.022*
C10	0.60456 (6)	−0.4846 (2)	0.68973 (4)	0.0169 (2)
C11	0.58026 (6)	−0.3347 (2)	0.64713 (5)	0.0190 (3)
H11A	0.5369	−0.3634	0.6337	0.023*
C12	0.61909 (6)	−0.1452 (2)	0.62452 (5)	0.0178 (2)
H12A	0.6023	−0.0442	0.5955	0.021*
C13	0.72290 (5)	0.1110 (2)	0.61966 (4)	0.0153 (2)
C14	0.58192 (6)	−0.8108 (3)	0.75519 (5)	0.0234 (3)
H14A	0.5460	−0.9247	0.7663	0.035*
H14B	0.5939	−0.6929	0.7846	0.035*
H14C	0.6201	−0.9169	0.7459	0.035*
H1N2	0.9418 (8)	1.458 (3)	0.4703 (6)	0.034 (4)*
H2N2	0.8766 (8)	1.285 (3)	0.4689 (6)	0.032 (4)*
H1O2	0.8018 (10)	0.309 (4)	0.6276 (7)	0.058 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0159 (4)	0.0188 (4)	0.0200 (4)	−0.0033 (3)	−0.0026 (3)	0.0024 (3)
O2	0.0167 (4)	0.0194 (4)	0.0186 (4)	−0.0041 (3)	−0.0020 (3)	0.0032 (3)
O3	0.0185 (4)	0.0197 (4)	0.0173 (4)	−0.0017 (3)	−0.0009 (3)	0.0034 (3)
O4	0.0183 (4)	0.0222 (4)	0.0223 (4)	−0.0053 (3)	0.0007 (3)	0.0062 (3)
N1	0.0174 (5)	0.0165 (5)	0.0187 (5)	−0.0004 (4)	0.0024 (4)	0.0005 (4)
N2	0.0161 (5)	0.0156 (5)	0.0170 (5)	−0.0022 (4)	−0.0009 (4)	0.0022 (4)
C1	0.0143 (5)	0.0213 (6)	0.0203 (6)	−0.0025 (4)	−0.0016 (4)	0.0026 (5)
C2	0.0192 (6)	0.0214 (6)	0.0196 (6)	0.0000 (5)	−0.0010 (4)	0.0057 (5)
C3	0.0160 (5)	0.0194 (6)	0.0196 (6)	−0.0020 (4)	0.0007 (4)	−0.0005 (4)
C4	0.0172 (5)	0.0180 (6)	0.0162 (5)	0.0006 (4)	−0.0006 (4)	0.0015 (4)
C5	0.0151 (5)	0.0138 (5)	0.0143 (5)	0.0004 (4)	0.0029 (4)	−0.0010 (4)
C6	0.0148 (5)	0.0143 (5)	0.0139 (5)	−0.0004 (4)	0.0017 (4)	−0.0019 (4)
C7	0.0155 (5)	0.0161 (5)	0.0143 (5)	−0.0014 (4)	0.0012 (4)	−0.0008 (4)
C8	0.0163 (5)	0.0183 (6)	0.0174 (6)	−0.0014 (4)	−0.0006 (4)	−0.0005 (4)
C9	0.0190 (5)	0.0182 (6)	0.0169 (6)	−0.0004 (4)	−0.0014 (4)	0.0020 (4)
C10	0.0188 (5)	0.0161 (5)	0.0158 (5)	−0.0025 (4)	0.0035 (4)	−0.0006 (4)
C11	0.0150 (5)	0.0222 (6)	0.0197 (6)	−0.0032 (4)	−0.0012 (4)	0.0005 (5)
C12	0.0177 (5)	0.0197 (6)	0.0160 (5)	−0.0006 (4)	−0.0008 (4)	0.0015 (4)
C13	0.0143 (5)	0.0158 (5)	0.0159 (5)	−0.0004 (4)	0.0013 (4)	−0.0012 (4)
C14	0.0248 (6)	0.0232 (6)	0.0223 (6)	−0.0035 (5)	0.0014 (5)	0.0074 (5)

Geometric parameters (Å, º)

O1—C6	1.2385 (14)	C4—C5	1.3891 (15)
O2—C13	1.3256 (14)	C4—H4A	0.9500
O2—H1O2	0.99 (2)	C5—C6	1.5144 (15)
O3—C13	1.2286 (14)	C7—C8	1.3919 (16)
O4—C10	1.3671 (14)	C7—C12	1.4014 (16)
O4—C14	1.4267 (14)	C7—C13	1.4898 (15)
N1—C2	1.3376 (15)	C8—C9	1.3984 (16)
N1—C3	1.3389 (15)	C8—H8A	0.9500
N2—C6	1.3329 (15)	C9—C10	1.3932 (16)
N2—H1N2	0.923 (17)	C9—H9A	0.9500
N2—H2N2	0.924 (18)	C10—C11	1.3967 (16)
C1—C2	1.3883 (16)	C11—C12	1.3797 (16)
C1—C5	1.3898 (16)	C11—H11A	0.9500
C1—H1A	0.9500	C12—H12A	0.9500
C2—H2A	0.9500	C14—H14A	0.9800
C3—C4	1.3931 (16)	C14—H14B	0.9800
C3—H3A	0.9500	C14—H14C	0.9800
C13—O2—H1O2	109.8 (11)	C12—C7—C13	119.04 (10)
C10—O4—C14	117.61 (9)	C7—C8—C9	121.01 (11)
C2—N1—C3	117.71 (10)	C7—C8—H8A	119.5
C6—N2—H1N2	116.8 (10)	C9—C8—H8A	119.5
C6—N2—H2N2	123.3 (10)	C10—C9—C8	119.12 (11)
H1N2—N2—H2N2	119.9 (14)	C10—C9—H9A	120.4
C2—C1—C5	119.03 (10)	C8—C9—H9A	120.4
C2—C1—H1A	120.5	O4—C10—C9	124.80 (10)
C5—C1—H1A	120.5	O4—C10—C11	115.01 (10)
N1—C2—C1	123.07 (11)	C9—C10—C11	120.19 (10)
N1—C2—H2A	118.5	C12—C11—C10	120.17 (10)
C1—C2—H2A	118.5	C12—C11—H11A	119.9
N1—C3—C4	123.14 (11)	C10—C11—H11A	119.9
N1—C3—H3A	118.4	C11—C12—C7	120.53 (11)
C4—C3—H3A	118.4	C11—C12—H12A	119.7
C5—C4—C3	118.72 (11)	C7—C12—H12A	119.7
C5—C4—H4A	120.6	O3—C13—O2	122.68 (10)
C3—C4—H4A	120.6	O3—C13—C7	122.82 (10)
C4—C5—C1	118.32 (10)	O2—C13—C7	114.50 (10)
C4—C5—C6	124.68 (10)	O4—C14—H14A	109.5
C1—C5—C6	117.00 (10)	O4—C14—H14B	109.5
O1—C6—N2	122.84 (10)	H14A—C14—H14B	109.5
O1—C6—C5	118.35 (10)	O4—C14—H14C	109.5
N2—C6—C5	118.80 (10)	H14A—C14—H14C	109.5
C8—C7—C12	118.94 (10)	H14B—C14—H14C	109.5
C8—C7—C13	122.01 (10)
C3—N1—C2—C1	−0.65 (18)	C7—C8—C9—C10	0.14 (17)
C5—C1—C2—N1	0.63 (19)	C14—O4—C10—C9	3.41 (17)
C2—N1—C3—C4	0.13 (17)	C14—O4—C10—C11	−176.55 (10)
N1—C3—C4—C5	0.38 (18)	C8—C9—C10—O4	−178.56 (11)
C3—C4—C5—C1	−0.38 (17)	C8—C9—C10—C11	1.40 (17)
C3—C4—C5—C6	179.87 (10)	O4—C10—C11—C12	178.55 (10)
C2—C1—C5—C4	−0.09 (17)	C9—C10—C11—C12	−1.42 (18)
C2—C1—C5—C6	179.68 (10)	C10—C11—C12—C7	−0.12 (18)
C4—C5—C6—O1	−179.37 (11)	C8—C7—C12—C11	1.64 (17)
C1—C5—C6—O1	0.88 (15)	C13—C7—C12—C11	−178.24 (10)
C4—C5—C6—N2	1.75 (16)	C8—C7—C13—O3	171.05 (11)
C1—C5—C6—N2	−178.00 (10)	C12—C7—C13—O3	−9.07 (17)
C12—C7—C8—C9	−1.65 (17)	C8—C7—C13—O2	−8.99 (16)
C13—C7—C8—C9	178.23 (10)	C12—C7—C13—O2	170.89 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1^i	0.921 (16)	1.996 (16)	2.9033 (13)	168.2 (13)
N2—H2N2···O3^ii	0.925 (16)	2.056 (16)	2.9679 (13)	168.4 (13)
O2—H1O2···N1	0.99 (2)	1.67 (2)	2.6603 (13)	177.8 (16)
C3—H3A···O3	0.95	2.60	3.2516 (14)	126
C4—H4A···O3^ii	0.95	2.46	3.3897 (14)	166
C11—H11A···O1^iii	0.95	2.43	3.0724 (15)	124
C14—H14A···O4^iv	0.98	2.58	3.5463 (16)	170

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

(mo_in4meo140_0m) Isonicotinamide 4-methoxybenzoic acid

Crystal data

C8H8O3·C6H6N2O	F(000) = 1152
Mr = 274.27	Dx = 1.396 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 20.332 (2) Å	Cell parameters from 4959 reflections
b = 5.1318 (5) Å	θ = 2.6–28.6°
c = 25.024 (2) Å	µ = 0.10 mm^−1
β = 90.917 (6)°	T = 140 K
V = 2610.7 (4) Å^3	Block, colourless
Z = 8	0.81 × 0.13 × 0.05 mm

Data collection

Bruker APEX Duo CCD area detector diffractometer	3345 independent reflections
Radiation source: fine-focus sealed tube	2666 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 28.7°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −27→27
Tmin = 0.890, Tmax = 0.969	k = −6→6
20244 measured reflections	l = −33→33

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0688P)^2 + 0.9686P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
3345 reflections	Δρmax = 0.31 e Å^−3
194 parameters	Δρmin = −0.23 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.

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

	x	y	z	Uiso*/Ueq
O1	0.99841 (4)	1.24270 (16)	0.54442 (3)	0.0227 (2)
O2	0.77833 (4)	0.16352 (17)	0.64538 (3)	0.0226 (2)
O3	0.70513 (4)	0.22785 (17)	0.57897 (3)	0.0232 (2)
O4	0.56136 (4)	−0.66036 (17)	0.70993 (3)	0.0265 (2)
N1	0.83978 (5)	0.56190 (19)	0.59969 (4)	0.0219 (2)
N2	0.91723 (5)	1.3239 (2)	0.48434 (4)	0.0200 (2)
C1	0.93304 (6)	0.8441 (2)	0.59301 (5)	0.0234 (3)
H1A	0.9752	0.8944	0.6063	0.028*
C2	0.89896 (6)	0.6423 (2)	0.61673 (5)	0.0253 (3)
H2A	0.9187	0.5569	0.6466	0.030*
C3	0.81256 (6)	0.6860 (2)	0.55788 (5)	0.0225 (3)
H3A	0.7704	0.6312	0.5454	0.027*
C4	0.84292 (6)	0.8914 (2)	0.53173 (5)	0.0209 (2)
H4A	0.8218	0.9751	0.5022	0.025*
C5	0.90462 (5)	0.9717 (2)	0.54954 (4)	0.0176 (2)
C6	0.94362 (5)	1.1915 (2)	0.52507 (4)	0.0176 (2)
C7	0.68289 (5)	−0.0999 (2)	0.64394 (4)	0.0187 (2)
C8	0.70728 (6)	−0.2530 (2)	0.68565 (5)	0.0216 (3)
H8A	0.7510	−0.2264	0.6985	0.026*
C9	0.66851 (6)	−0.4452 (2)	0.70898 (5)	0.0224 (3)
H9A	0.6856	−0.5485	0.7375	0.027*
C10	0.60467 (6)	−0.4835 (2)	0.68993 (4)	0.0206 (2)
C11	0.58038 (6)	−0.3344 (2)	0.64723 (5)	0.0237 (3)
H11A	0.5370	−0.3636	0.6338	0.028*
C12	0.61899 (6)	−0.1455 (2)	0.62455 (5)	0.0222 (3)
H12A	0.6021	−0.0452	0.5955	0.027*
C13	0.72257 (5)	0.1115 (2)	0.61961 (4)	0.0189 (2)
C14	0.58195 (7)	−0.8080 (3)	0.75547 (5)	0.0309 (3)
H14A	0.5460	−0.9219	0.7666	0.046*
H14B	0.5938	−0.6894	0.7848	0.046*
H14C	0.6202	−0.9142	0.7463	0.046*
H1N2	0.9415 (8)	1.460 (3)	0.4713 (6)	0.040 (4)*
H2N2	0.8771 (8)	1.280 (3)	0.4692 (6)	0.034 (4)*
H1O2	0.8007 (10)	0.307 (4)	0.6289 (7)	0.063 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0189 (4)	0.0242 (4)	0.0249 (4)	−0.0050 (3)	−0.0046 (3)	0.0031 (3)
O2	0.0186 (4)	0.0254 (4)	0.0237 (4)	−0.0055 (3)	−0.0041 (3)	0.0045 (3)
O3	0.0217 (4)	0.0253 (4)	0.0224 (4)	−0.0027 (3)	−0.0030 (3)	0.0052 (3)
O4	0.0225 (4)	0.0282 (5)	0.0288 (5)	−0.0070 (4)	0.0004 (3)	0.0075 (4)
N1	0.0201 (5)	0.0213 (5)	0.0241 (5)	−0.0013 (4)	0.0012 (4)	0.0021 (4)
N2	0.0182 (5)	0.0193 (5)	0.0225 (5)	−0.0027 (4)	−0.0028 (4)	0.0028 (4)
C1	0.0171 (5)	0.0269 (6)	0.0261 (6)	−0.0030 (5)	−0.0041 (4)	0.0045 (5)
C2	0.0228 (6)	0.0275 (6)	0.0256 (6)	−0.0008 (5)	−0.0031 (5)	0.0082 (5)
C3	0.0189 (6)	0.0240 (6)	0.0247 (6)	−0.0033 (5)	−0.0004 (4)	0.0009 (5)
C4	0.0192 (5)	0.0229 (6)	0.0205 (5)	−0.0008 (4)	−0.0019 (4)	0.0026 (4)
C5	0.0173 (5)	0.0166 (5)	0.0190 (5)	0.0001 (4)	0.0018 (4)	−0.0008 (4)
C6	0.0174 (5)	0.0172 (5)	0.0182 (5)	−0.0003 (4)	0.0004 (4)	−0.0019 (4)
C7	0.0176 (5)	0.0198 (5)	0.0188 (5)	−0.0019 (4)	0.0005 (4)	−0.0005 (4)
C8	0.0189 (5)	0.0228 (6)	0.0229 (6)	−0.0020 (4)	−0.0024 (4)	0.0010 (4)
C9	0.0224 (6)	0.0228 (6)	0.0221 (6)	−0.0014 (4)	−0.0025 (4)	0.0037 (4)
C10	0.0211 (6)	0.0204 (5)	0.0204 (5)	−0.0031 (4)	0.0028 (4)	−0.0001 (4)
C11	0.0173 (5)	0.0290 (6)	0.0245 (6)	−0.0039 (5)	−0.0029 (4)	0.0024 (5)
C12	0.0199 (6)	0.0262 (6)	0.0206 (5)	−0.0012 (5)	−0.0028 (4)	0.0035 (5)
C13	0.0166 (5)	0.0205 (5)	0.0195 (5)	−0.0001 (4)	0.0004 (4)	−0.0008 (4)
C14	0.0321 (7)	0.0310 (7)	0.0297 (7)	−0.0061 (5)	0.0023 (5)	0.0108 (5)

Geometric parameters (Å, º)

O1—C6	1.2359 (14)	C4—C5	1.3872 (15)
O2—C13	1.3224 (14)	C4—H4A	0.9500
O2—H1O2	0.96 (2)	C5—C6	1.5139 (15)
O3—C13	1.2268 (14)	C7—C8	1.3916 (16)
O4—C10	1.3652 (14)	C7—C12	1.3993 (16)
O4—C14	1.4257 (15)	C7—C13	1.4881 (16)
N1—C2	1.3356 (15)	C8—C9	1.3963 (16)
N1—C3	1.3373 (15)	C8—H8A	0.9500
N2—C6	1.3308 (14)	C9—C10	1.3894 (16)
N2—H1N2	0.920 (18)	C9—H9A	0.9500
N2—H2N2	0.921 (17)	C10—C11	1.3982 (16)
C1—C2	1.3850 (17)	C11—C12	1.3756 (17)
C1—C5	1.3874 (15)	C11—H11A	0.9500
C1—H1A	0.9500	C12—H12A	0.9500
C2—H2A	0.9500	C14—H14A	0.9800
C3—C4	1.3903 (17)	C14—H14B	0.9800
C3—H3A	0.9500	C14—H14C	0.9800
C13—O2—H1O2	110.7 (12)	C12—C7—C13	119.11 (10)
C10—O4—C14	117.60 (10)	C7—C8—C9	121.05 (11)
C2—N1—C3	117.53 (10)	C7—C8—H8A	119.5
C6—N2—H1N2	116.7 (10)	C9—C8—H8A	119.5
C6—N2—H2N2	122.3 (10)	C10—C9—C8	119.14 (11)
H1N2—N2—H2N2	121.0 (14)	C10—C9—H9A	120.4
C2—C1—C5	118.94 (11)	C8—C9—H9A	120.4
C2—C1—H1A	120.5	O4—C10—C9	124.94 (10)
C5—C1—H1A	120.5	O4—C10—C11	114.96 (10)
N1—C2—C1	123.27 (11)	C9—C10—C11	120.09 (10)
N1—C2—H2A	118.4	C12—C11—C10	120.27 (11)
C1—C2—H2A	118.4	C12—C11—H11A	119.9
N1—C3—C4	123.23 (11)	C10—C11—H11A	119.9
N1—C3—H3A	118.4	C11—C12—C7	120.51 (11)
C4—C3—H3A	118.4	C11—C12—H12A	119.7
C5—C4—C3	118.68 (10)	C7—C12—H12A	119.7
C5—C4—H4A	120.7	O3—C13—O2	122.71 (10)
C3—C4—H4A	120.7	O3—C13—C7	122.85 (10)
C4—C5—C1	118.36 (10)	O2—C13—C7	114.44 (10)
C4—C5—C6	124.61 (10)	O4—C14—H14A	109.5
C1—C5—C6	117.02 (10)	O4—C14—H14B	109.5
O1—C6—N2	122.77 (10)	H14A—C14—H14B	109.5
O1—C6—C5	118.33 (10)	O4—C14—H14C	109.5
N2—C6—C5	118.89 (10)	H14A—C14—H14C	109.5
C8—C7—C12	118.90 (10)	H14B—C14—H14C	109.5
C8—C7—C13	121.98 (10)
C3—N1—C2—C1	−0.59 (19)	C7—C8—C9—C10	0.19 (18)
C5—C1—C2—N1	0.4 (2)	C14—O4—C10—C9	3.28 (18)
C2—N1—C3—C4	0.23 (18)	C14—O4—C10—C11	−176.51 (11)
N1—C3—C4—C5	0.30 (19)	C8—C9—C10—O4	−178.51 (11)
C3—C4—C5—C1	−0.46 (17)	C8—C9—C10—C11	1.28 (18)
C3—C4—C5—C6	179.90 (10)	O4—C10—C11—C12	178.49 (11)
C2—C1—C5—C4	0.13 (18)	C9—C10—C11—C12	−1.32 (19)
C2—C1—C5—C6	179.79 (10)	C10—C11—C12—C7	−0.13 (19)
C4—C5—C6—O1	−179.41 (11)	C8—C7—C12—C11	1.56 (18)
C1—C5—C6—O1	0.95 (16)	C13—C7—C12—C11	−178.09 (11)
C4—C5—C6—N2	1.65 (17)	C8—C7—C13—O3	171.19 (11)
C1—C5—C6—N2	−177.99 (10)	C12—C7—C13—O3	−9.16 (17)
C12—C7—C8—C9	−1.60 (18)	C8—C7—C13—O2	−8.70 (16)
C13—C7—C8—C9	178.05 (11)	C12—C7—C13—O2	170.95 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1^i	0.918 (16)	1.998 (16)	2.9062 (13)	170.0 (14)
N2—H2N2···O3^ii	0.922 (16)	2.063 (16)	2.9692 (13)	167.3 (13)
O2—H1O2···N1	0.96 (2)	1.70 (2)	2.6634 (13)	180 (2)
C4—H4A···O3^ii	0.95	2.46	3.3945 (15)	166
C11—H11A···O1^iii	0.95	2.44	3.0791 (15)	125
C14—H14A···O4^iv	0.98	2.58	3.5483 (17)	170

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

(mo_in4meo142_0m) Isonicotinamide 4-methoxybenzoic acid

Crystal data

C8H8O3·C6H6N2O	F(000) = 1152
Mr = 274.27	Dx = 1.401 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 20.296 (7) Å	Cell parameters from 3184 reflections
b = 5.1263 (18) Å	θ = 2.6–28.7°
c = 25.005 (9) Å	µ = 0.10 mm^−1
β = 90.95 (2)°	T = 142 K
V = 2601.2 (16) Å^3	Block, colourless
Z = 8	0.81 × 0.13 × 0.05 mm

Data collection

Bruker APEX Duo CCD area detector diffractometer	3363 independent reflections
Radiation source: fine-focus sealed tube	2502 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
φ and ω scans	θmax = 28.8°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −27→27
Tmin = 0.769, Tmax = 0.969	k = −6→6
14782 measured reflections	l = −33→33

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.133	w = 1/[σ^2(Fo^2) + (0.0729P)^2 + 0.7112P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
3363 reflections	Δρmax = 0.31 e Å^−3
194 parameters	Δρmin = −0.24 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.

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

	x	y	z	Uiso*/Ueq
O1	0.99842 (5)	1.24307 (18)	0.54447 (4)	0.0241 (2)
O2	0.77837 (5)	0.16395 (19)	0.64536 (4)	0.0236 (2)
O3	0.70514 (5)	0.22770 (19)	0.57901 (4)	0.0240 (2)
O4	0.56137 (5)	−0.66005 (19)	0.70995 (4)	0.0278 (3)
N1	0.83976 (5)	0.5619 (2)	0.59967 (4)	0.0230 (3)
N2	0.91727 (6)	1.3243 (2)	0.48431 (4)	0.0209 (3)
C1	0.93303 (7)	0.8442 (3)	0.59299 (5)	0.0245 (3)
H1A	0.9752	0.8948	0.6063	0.029*
C2	0.89904 (7)	0.6425 (3)	0.61675 (6)	0.0266 (3)
H2A	0.9188	0.5571	0.6467	0.032*
C3	0.81270 (7)	0.6861 (3)	0.55785 (6)	0.0233 (3)
H3A	0.7705	0.6312	0.5453	0.028*
C4	0.84303 (6)	0.8913 (3)	0.53178 (5)	0.0220 (3)
H4A	0.8219	0.9751	0.5023	0.026*
C5	0.90473 (6)	0.9715 (2)	0.54952 (5)	0.0184 (3)
C6	0.94349 (6)	1.1916 (2)	0.52509 (5)	0.0185 (3)
C7	0.68298 (6)	−0.0997 (3)	0.64400 (5)	0.0197 (3)
C8	0.70712 (7)	−0.2528 (3)	0.68567 (5)	0.0227 (3)
H8A	0.7509	−0.2259	0.6986	0.027*
C9	0.66850 (6)	−0.4450 (3)	0.70898 (5)	0.0236 (3)
H9A	0.6856	−0.5484	0.7375	0.028*
C10	0.60455 (6)	−0.4834 (3)	0.68986 (5)	0.0216 (3)
C11	0.58037 (7)	−0.3342 (3)	0.64727 (5)	0.0246 (3)
H11A	0.5369	−0.3630	0.6339	0.030*
C12	0.61906 (7)	−0.1458 (3)	0.62461 (5)	0.0232 (3)
H12A	0.6022	−0.0458	0.5955	0.028*
C13	0.72263 (6)	0.1115 (3)	0.61959 (5)	0.0200 (3)
C14	0.58194 (8)	−0.8078 (3)	0.75548 (6)	0.0314 (3)
H14A	0.5461	−0.9236	0.7663	0.047*
H14B	0.5932	−0.6892	0.7850	0.047*
H14C	0.6207	−0.9122	0.7465	0.047*
H1N2	0.9417 (8)	1.463 (4)	0.4713 (7)	0.039 (5)*
H2N2	0.8764 (9)	1.280 (4)	0.4704 (7)	0.039 (5)*
H1O2	0.8013 (11)	0.309 (4)	0.6281 (8)	0.068 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0209 (5)	0.0240 (5)	0.0271 (5)	−0.0049 (4)	−0.0056 (4)	0.0024 (4)
O2	0.0211 (5)	0.0248 (5)	0.0247 (5)	−0.0056 (4)	−0.0048 (4)	0.0042 (4)
O3	0.0235 (5)	0.0257 (5)	0.0227 (5)	−0.0022 (4)	−0.0033 (4)	0.0053 (4)
O4	0.0249 (5)	0.0288 (5)	0.0296 (6)	−0.0069 (4)	−0.0006 (4)	0.0081 (4)
N1	0.0222 (6)	0.0211 (6)	0.0256 (6)	−0.0016 (5)	0.0006 (4)	0.0016 (5)
N2	0.0200 (6)	0.0195 (6)	0.0229 (6)	−0.0031 (4)	−0.0032 (4)	0.0033 (4)
C1	0.0190 (6)	0.0278 (7)	0.0265 (7)	−0.0031 (5)	−0.0053 (5)	0.0051 (6)
C2	0.0250 (7)	0.0277 (7)	0.0269 (7)	−0.0001 (6)	−0.0037 (6)	0.0079 (6)
C3	0.0199 (6)	0.0246 (7)	0.0251 (7)	−0.0026 (5)	−0.0019 (5)	0.0002 (5)
C4	0.0215 (6)	0.0228 (7)	0.0215 (7)	−0.0009 (5)	−0.0030 (5)	0.0020 (5)
C5	0.0194 (6)	0.0170 (6)	0.0189 (6)	0.0000 (5)	0.0006 (5)	−0.0015 (5)
C6	0.0184 (6)	0.0179 (6)	0.0191 (6)	−0.0002 (5)	−0.0007 (5)	−0.0023 (5)
C7	0.0196 (6)	0.0202 (6)	0.0191 (6)	−0.0019 (5)	−0.0011 (5)	−0.0013 (5)
C8	0.0213 (7)	0.0235 (7)	0.0233 (7)	−0.0022 (5)	−0.0039 (5)	0.0011 (5)
C9	0.0242 (7)	0.0228 (7)	0.0235 (7)	−0.0012 (5)	−0.0045 (5)	0.0037 (5)
C10	0.0225 (7)	0.0206 (6)	0.0218 (7)	−0.0029 (5)	0.0017 (5)	−0.0002 (5)
C11	0.0186 (6)	0.0295 (7)	0.0257 (7)	−0.0041 (5)	−0.0039 (5)	0.0031 (6)
C12	0.0215 (6)	0.0262 (7)	0.0216 (7)	−0.0010 (5)	−0.0032 (5)	0.0035 (5)
C13	0.0189 (6)	0.0206 (6)	0.0205 (6)	0.0000 (5)	−0.0012 (5)	−0.0014 (5)
C14	0.0334 (8)	0.0311 (8)	0.0297 (8)	−0.0064 (6)	0.0015 (6)	0.0108 (6)

Geometric parameters (Å, º)

O1—C6	1.2367 (16)	C4—C5	1.3840 (18)
O2—C13	1.3205 (16)	C4—H4A	0.9500
O2—H1O2	0.98 (2)	C5—C6	1.5103 (18)
O3—C13	1.2241 (16)	C7—C8	1.3872 (18)
O4—C10	1.3619 (16)	C7—C12	1.3976 (18)
O4—C14	1.4242 (17)	C7—C13	1.4860 (18)
N1—C3	1.3347 (18)	C8—C9	1.3931 (19)
N1—C2	1.3355 (18)	C8—H8A	0.9500
N2—C6	1.3294 (17)	C9—C10	1.3897 (19)
N2—H1N2	0.927 (19)	C9—H9A	0.9500
N2—H2N2	0.92 (2)	C10—C11	1.3937 (19)
C1—C2	1.3826 (19)	C11—C12	1.3732 (19)
C1—C5	1.3845 (18)	C11—H11A	0.9500
C1—H1A	0.9500	C12—H12A	0.9500
C2—H2A	0.9500	C14—H14A	0.9800
C3—C4	1.3867 (19)	C14—H14B	0.9800
C3—H3A	0.9500	C14—H14C	0.9800
C13—O2—H1O2	110.4 (13)	C12—C7—C13	119.11 (12)
C10—O4—C14	117.81 (11)	C7—C8—C9	121.35 (12)
C3—N1—C2	117.38 (12)	C7—C8—H8A	119.3
C6—N2—H1N2	116.8 (11)	C9—C8—H8A	119.3
C6—N2—H2N2	120.7 (11)	C10—C9—C8	119.02 (12)
H1N2—N2—H2N2	122.5 (15)	C10—C9—H9A	120.5
C2—C1—C5	119.10 (12)	C8—C9—H9A	120.5
C2—C1—H1A	120.5	O4—C10—C9	124.77 (12)
C5—C1—H1A	120.5	O4—C10—C11	115.22 (12)
N1—C2—C1	123.17 (13)	C9—C10—C11	120.01 (12)
N1—C2—H2A	118.4	C12—C11—C10	120.33 (12)
C1—C2—H2A	118.4	C12—C11—H11A	119.8
N1—C3—C4	123.36 (12)	C10—C11—H11A	119.8
N1—C3—H3A	118.3	C11—C12—C7	120.64 (12)
C4—C3—H3A	118.3	C11—C12—H12A	119.7
C5—C4—C3	118.75 (12)	C7—C12—H12A	119.7
C5—C4—H4A	120.6	O3—C13—O2	122.65 (12)
C3—C4—H4A	120.6	O3—C13—C7	122.93 (12)
C4—C5—C1	118.23 (12)	O2—C13—C7	114.42 (11)
C4—C5—C6	124.54 (11)	O4—C14—H14A	109.5
C1—C5—C6	117.22 (11)	O4—C14—H14B	109.5
O1—C6—N2	122.56 (12)	H14A—C14—H14B	109.5
O1—C6—C5	118.25 (11)	O4—C14—H14C	109.5
N2—C6—C5	119.19 (11)	H14A—C14—H14C	109.5
C8—C7—C12	118.63 (12)	H14B—C14—H14C	109.5
C8—C7—C13	122.25 (12)
C3—N1—C2—C1	−0.5 (2)	C7—C8—C9—C10	0.1 (2)
C5—C1—C2—N1	0.3 (2)	C14—O4—C10—C9	3.2 (2)
C2—N1—C3—C4	0.1 (2)	C14—O4—C10—C11	−176.46 (12)
N1—C3—C4—C5	0.5 (2)	C8—C9—C10—O4	−178.35 (12)
C3—C4—C5—C1	−0.7 (2)	C8—C9—C10—C11	1.3 (2)
C3—C4—C5—C6	−179.96 (12)	O4—C10—C11—C12	178.52 (12)
C2—C1—C5—C4	0.3 (2)	C9—C10—C11—C12	−1.1 (2)
C2—C1—C5—C6	179.65 (12)	C10—C11—C12—C7	−0.3 (2)
C4—C5—C6—O1	−179.50 (13)	C8—C7—C12—C11	1.6 (2)
C1—C5—C6—O1	1.20 (18)	C13—C7—C12—C11	−178.08 (12)
C4—C5—C6—N2	1.34 (19)	C8—C7—C13—O3	171.32 (13)
C1—C5—C6—N2	−177.97 (12)	C12—C7—C13—O3	−9.0 (2)
C12—C7—C8—C9	−1.5 (2)	C8—C7—C13—O2	−8.79 (19)
C13—C7—C8—C9	178.21 (12)	C12—C7—C13—O2	170.93 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1^i	0.929 (19)	1.980 (19)	2.8992 (18)	170.3 (15)
N2—H2N2···O3^ii	0.923 (18)	2.066 (18)	2.9655 (19)	164.5 (16)
O2—H1O2···N1	0.98 (2)	1.68 (2)	2.6583 (17)	178.6 (17)
C4—H4A···O3^ii	0.95	2.46	3.393 (2)	166
C11—H11A···O1^iii	0.95	2.44	3.074 (2)	124
C14—H14A···O4^iv	0.98	2.57	3.543 (2)	170

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

(mo_in4meo143_0m) Isonicotinamide 4-methoxybenzoic acid

Crystal data

C8H8O3·C6H6N2O	F(000) = 1152
Mr = 274.27	Dx = 1.388 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 20.088 (5) Å	Cell parameters from 3029 reflections
b = 5.2242 (12) Å	θ = 2.6–27.5°
c = 25.033 (6) Å	µ = 0.10 mm^−1
β = 92.308 (16)°	T = 143 K
V = 2624.9 (11) Å^3	Block, colourless
Z = 8	0.81 × 0.13 × 0.05 mm

Data collection

Bruker APEX Duo CCD area detector diffractometer	3236 independent reflections
Radiation source: fine-focus sealed tube	2362 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
φ and ω scans	θmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −26→26
Tmin = 0.523, Tmax = 0.746	k = −6→6
14186 measured reflections	l = −33→33

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.134	w = 1/[σ^2(Fo^2) + (0.0752P)^2 + 0.3732P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
3236 reflections	Δρmax = 0.27 e Å^−3
194 parameters	Δρmin = −0.24 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.

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

	x	y	z	Uiso*/Ueq
O1	1.00104 (5)	1.24472 (19)	0.54425 (4)	0.0263 (3)
O2	0.76805 (6)	0.2656 (2)	0.65588 (4)	0.0345 (3)
H1O2	0.7956 (11)	0.394 (5)	0.6366 (9)	0.069 (7)*
O3	0.70578 (5)	0.24350 (19)	0.58014 (4)	0.0272 (3)
O4	0.56198 (5)	−0.5874 (2)	0.72035 (4)	0.0298 (3)
N1	0.83838 (6)	0.5976 (2)	0.60185 (5)	0.0270 (3)
N2	0.91602 (6)	1.3348 (2)	0.48566 (5)	0.0241 (3)
H1N2	0.9394 (9)	1.465 (3)	0.4730 (7)	0.037 (5)*
H2N2	0.8753 (10)	1.295 (3)	0.4684 (7)	0.036 (5)*
C1	0.93735 (7)	0.8392 (3)	0.58907 (6)	0.0257 (3)
H1A	0.9829	0.8693	0.5988	0.031*
C2	0.90241 (8)	0.6492 (3)	0.61405 (6)	0.0289 (3)
H2A	0.9248	0.5507	0.6411	0.035*
C3	0.80782 (8)	0.7366 (3)	0.56326 (6)	0.0283 (3)
H3A	0.7626	0.6995	0.5538	0.034*
C4	0.83896 (7)	0.9319 (3)	0.53640 (6)	0.0263 (3)
H4A	0.8153	1.0274	0.5095	0.032*
C5	0.90544 (7)	0.9858 (3)	0.54955 (5)	0.0210 (3)
C6	0.94448 (7)	1.1993 (3)	0.52529 (5)	0.0208 (3)
C7	0.67701 (7)	−0.0207 (3)	0.65336 (5)	0.0236 (3)
C8	0.68727 (8)	−0.0783 (3)	0.70733 (6)	0.0317 (4)
H8A	0.7204	0.0117	0.7279	0.038*
C9	0.64965 (8)	−0.2659 (3)	0.73165 (6)	0.0326 (4)
H9A	0.6568	−0.3031	0.7686	0.039*
C10	0.60158 (7)	−0.3979 (3)	0.70130 (6)	0.0247 (3)
C11	0.59008 (8)	−0.3390 (3)	0.64770 (6)	0.0289 (3)
H11A	0.5566	−0.4277	0.6272	0.035*
C12	0.62733 (7)	−0.1513 (3)	0.62421 (6)	0.0278 (3)
H12A	0.6189	−0.1107	0.5876	0.033*
C13	0.71733 (7)	0.1745 (3)	0.62627 (6)	0.0245 (3)
C14	0.56935 (9)	−0.6496 (4)	0.77560 (7)	0.0428 (4)
H14A	0.5408	−0.7960	0.7834	0.064*
H14B	0.5564	−0.5022	0.7970	0.064*
H14C	0.6159	−0.6935	0.7844	0.064*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0213 (5)	0.0276 (5)	0.0293 (6)	−0.0050 (4)	−0.0080 (4)	0.0042 (4)
O2	0.0298 (6)	0.0438 (7)	0.0290 (6)	−0.0176 (5)	−0.0091 (5)	0.0079 (5)
O3	0.0230 (5)	0.0318 (6)	0.0265 (6)	−0.0023 (4)	−0.0049 (4)	0.0048 (4)
O4	0.0266 (6)	0.0332 (6)	0.0295 (6)	−0.0068 (5)	−0.0021 (4)	0.0072 (5)
N1	0.0266 (7)	0.0276 (6)	0.0265 (6)	−0.0045 (5)	−0.0007 (5)	0.0020 (5)
N2	0.0210 (6)	0.0246 (6)	0.0263 (7)	−0.0040 (5)	−0.0049 (5)	0.0040 (5)
C1	0.0210 (7)	0.0294 (8)	0.0264 (7)	−0.0018 (6)	−0.0043 (6)	0.0030 (6)
C2	0.0283 (8)	0.0301 (8)	0.0280 (8)	−0.0019 (6)	−0.0047 (6)	0.0062 (6)
C3	0.0201 (7)	0.0317 (8)	0.0328 (8)	−0.0037 (6)	−0.0025 (6)	0.0028 (6)
C4	0.0222 (7)	0.0276 (7)	0.0285 (7)	−0.0011 (6)	−0.0046 (6)	0.0040 (6)
C5	0.0208 (7)	0.0202 (7)	0.0219 (7)	0.0002 (5)	−0.0008 (5)	−0.0018 (5)
C6	0.0202 (7)	0.0211 (7)	0.0208 (7)	0.0000 (5)	−0.0016 (5)	−0.0026 (5)
C7	0.0187 (7)	0.0266 (7)	0.0252 (7)	−0.0014 (6)	−0.0021 (5)	0.0011 (6)
C8	0.0282 (8)	0.0395 (9)	0.0266 (8)	−0.0096 (7)	−0.0071 (6)	0.0020 (7)
C9	0.0291 (8)	0.0445 (10)	0.0238 (8)	−0.0096 (7)	−0.0047 (6)	0.0063 (7)
C10	0.0200 (7)	0.0269 (7)	0.0272 (7)	−0.0003 (6)	0.0004 (5)	0.0027 (6)
C11	0.0257 (8)	0.0333 (8)	0.0271 (8)	−0.0073 (6)	−0.0060 (6)	0.0002 (6)
C12	0.0261 (8)	0.0333 (8)	0.0236 (7)	−0.0034 (6)	−0.0052 (6)	0.0042 (6)
C13	0.0196 (7)	0.0273 (7)	0.0264 (7)	0.0004 (6)	−0.0037 (5)	0.0004 (6)
C14	0.0406 (10)	0.0535 (11)	0.0338 (9)	−0.0156 (9)	−0.0045 (7)	0.0157 (8)

Geometric parameters (Å, º)

O1—C6	1.2366 (17)	C4—C5	1.391 (2)
O2—C13	1.3241 (17)	C4—H4A	0.9500
O2—H1O2	1.01 (2)	C5—C6	1.5053 (19)
O3—C13	1.2230 (17)	C7—C12	1.391 (2)
O4—C10	1.3677 (17)	C7—C8	1.391 (2)
O4—C14	1.4228 (19)	C7—C13	1.483 (2)
N1—C2	1.3374 (19)	C8—C9	1.393 (2)
N1—C3	1.3377 (19)	C8—H8A	0.9500
N2—C6	1.3290 (18)	C9—C10	1.388 (2)
N2—H1N2	0.891 (19)	C9—H9A	0.9500
N2—H2N2	0.933 (19)	C10—C11	1.387 (2)
C1—C2	1.380 (2)	C11—C12	1.379 (2)
C1—C5	1.3875 (19)	C11—H11A	0.9500
C1—H1A	0.9500	C12—H12A	0.9500
C2—H2A	0.9500	C14—H14A	0.9800
C3—C4	1.385 (2)	C14—H14B	0.9800
C3—H3A	0.9500	C14—H14C	0.9800
C13—O2—H1O2	113.5 (12)	C8—C7—C13	122.03 (13)
C10—O4—C14	117.72 (12)	C7—C8—C9	120.99 (14)
C2—N1—C3	117.69 (13)	C7—C8—H8A	119.5
C6—N2—H1N2	116.9 (11)	C9—C8—H8A	119.5
C6—N2—H2N2	124.8 (11)	C10—C9—C8	119.23 (14)
H1N2—N2—H2N2	118.0 (16)	C10—C9—H9A	120.4
C2—C1—C5	119.44 (14)	C8—C9—H9A	120.4
C2—C1—H1A	120.3	O4—C10—C11	114.92 (13)
C5—C1—H1A	120.3	O4—C10—C9	124.78 (13)
N1—C2—C1	122.93 (14)	C11—C10—C9	120.30 (14)
N1—C2—H2A	118.5	C12—C11—C10	119.88 (13)
C1—C2—H2A	118.5	C12—C11—H11A	120.1
N1—C3—C4	123.17 (13)	C10—C11—H11A	120.1
N1—C3—H3A	118.4	C11—C12—C7	121.00 (13)
C4—C3—H3A	118.4	C11—C12—H12A	119.5
C3—C4—C5	118.84 (13)	C7—C12—H12A	119.5
C3—C4—H4A	120.6	O3—C13—O2	122.35 (13)
C5—C4—H4A	120.6	O3—C13—C7	123.23 (13)
C1—C5—C4	117.92 (13)	O2—C13—C7	114.41 (12)
C1—C5—C6	117.62 (12)	O4—C14—H14A	109.5
C4—C5—C6	124.42 (12)	O4—C14—H14B	109.5
O1—C6—N2	123.06 (13)	H14A—C14—H14B	109.5
O1—C6—C5	118.21 (12)	O4—C14—H14C	109.5
N2—C6—C5	118.70 (12)	H14A—C14—H14C	109.5
C12—C7—C8	118.57 (13)	H14B—C14—H14C	109.5
C12—C7—C13	119.40 (13)
C3—N1—C2—C1	0.7 (2)	C7—C8—C9—C10	0.4 (2)
C5—C1—C2—N1	0.2 (2)	C14—O4—C10—C11	−177.43 (15)
C2—N1—C3—C4	−1.1 (2)	C14—O4—C10—C9	1.7 (2)
N1—C3—C4—C5	0.7 (2)	C8—C9—C10—O4	179.36 (14)
C2—C1—C5—C4	−0.6 (2)	C8—C9—C10—C11	−1.6 (2)
C2—C1—C5—C6	177.05 (13)	O4—C10—C11—C12	−179.77 (14)
C3—C4—C5—C1	0.2 (2)	C9—C10—C11—C12	1.1 (2)
C3—C4—C5—C6	−177.30 (13)	C10—C11—C12—C7	0.6 (2)
C1—C5—C6—O1	−4.99 (19)	C8—C7—C12—C11	−1.7 (2)
C4—C5—C6—O1	172.55 (14)	C13—C7—C12—C11	178.21 (14)
C1—C5—C6—N2	176.92 (13)	C12—C7—C13—O3	6.2 (2)
C4—C5—C6—N2	−5.5 (2)	C8—C7—C13—O3	−173.82 (15)
C12—C7—C8—C9	1.2 (2)	C12—C7—C13—O2	−172.54 (13)
C13—C7—C8—C9	−178.73 (14)	C8—C7—C13—O2	7.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N1	1.01 (2)	1.64 (2)	2.6434 (17)	177 (2)
N2—H1N2···O1^i	0.892 (17)	1.990 (17)	2.8744 (17)	171.1 (16)
N2—H2N2···O3^ii	0.933 (19)	2.011 (19)	2.9330 (17)	169.6 (15)
C4—H4A···O3^ii	0.95	2.53	3.429 (2)	157
C11—H11A···O1^iii	0.95	2.51	3.127 (2)	123
C14—H14A···O4^iv	0.98	2.56	3.496 (2)	159

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

(mo_in4meo150_0m) Isonicotinamide 4-methoxybenzoic acid

Crystal data

C8H8O3·C6H6N2O	F(000) = 1152
Mr = 274.27	Dx = 1.389 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 20.084 (2) Å	Cell parameters from 4895 reflections
b = 5.2206 (6) Å	θ = 2.6–28.8°
c = 25.040 (3) Å	µ = 0.10 mm^−1
β = 92.375 (8)°	T = 150 K
V = 2623.2 (5) Å^3	Block, colourless
Z = 8	0.81 × 0.13 × 0.05 mm

Data collection

Bruker APEX Duo CCD area detector diffractometer	3520 independent reflections
Radiation source: fine-focus sealed tube	2765 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 29.2°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −27→27
Tmin = 0.915, Tmax = 0.969	k = −7→7
21034 measured reflections	l = −34→34

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0672P)^2 + 0.9974P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
3520 reflections	Δρmax = 0.31 e Å^−3
194 parameters	Δρmin = −0.19 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.

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

	x	y	z	Uiso*/Ueq
O1	1.00105 (4)	1.24515 (16)	0.54426 (3)	0.0259 (2)
O2	0.76799 (5)	0.26540 (19)	0.65585 (4)	0.0342 (3)
H1O2	0.7940 (10)	0.386 (4)	0.6360 (8)	0.073 (6)*
O3	0.70571 (4)	0.24354 (17)	0.58014 (3)	0.0268 (2)
O4	0.56200 (4)	−0.58732 (18)	0.72039 (3)	0.0299 (2)
N1	0.83830 (5)	0.5979 (2)	0.60184 (4)	0.0265 (2)
N2	0.91604 (5)	1.3347 (2)	0.48565 (4)	0.0236 (2)
H1N2	0.9399 (8)	1.469 (3)	0.4731 (6)	0.037 (4)*
H2N2	0.8761 (8)	1.297 (3)	0.4693 (6)	0.029 (4)*
C1	0.93755 (6)	0.8393 (2)	0.58907 (5)	0.0249 (3)
H1A	0.9831	0.8695	0.5988	0.030*
C2	0.90245 (6)	0.6492 (3)	0.61392 (5)	0.0283 (3)
H2A	0.9249	0.5500	0.6409	0.034*
C3	0.80776 (6)	0.7365 (2)	0.56324 (5)	0.0281 (3)
H3A	0.7625	0.6993	0.5537	0.034*
C4	0.83903 (6)	0.9323 (2)	0.53635 (5)	0.0259 (3)
H4A	0.8155	1.0279	0.5094	0.031*
C5	0.90536 (6)	0.9855 (2)	0.54962 (4)	0.0205 (2)
C6	0.94449 (6)	1.1995 (2)	0.52532 (4)	0.0202 (2)
C7	0.67698 (6)	−0.0203 (2)	0.65340 (5)	0.0230 (2)
C8	0.68741 (6)	−0.0781 (3)	0.70733 (5)	0.0309 (3)
H8A	0.7207	0.0116	0.7279	0.037*
C9	0.64976 (7)	−0.2654 (3)	0.73162 (5)	0.0321 (3)
H9A	0.6570	−0.3025	0.7686	0.039*
C10	0.60149 (6)	−0.3978 (2)	0.70132 (5)	0.0245 (3)
C11	0.59007 (6)	−0.3390 (3)	0.64776 (5)	0.0285 (3)
H11A	0.5566	−0.4280	0.6273	0.034*
C12	0.62735 (6)	−0.1511 (3)	0.62411 (5)	0.0272 (3)
H12A	0.6190	−0.1107	0.5875	0.033*
C13	0.71729 (6)	0.1749 (2)	0.62628 (5)	0.0236 (3)
C14	0.56939 (8)	−0.6487 (3)	0.77558 (6)	0.0431 (4)
H14A	0.5401	−0.7927	0.7836	0.065*
H14B	0.5573	−0.4997	0.7969	0.065*
H14C	0.6158	−0.6961	0.7843	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0216 (4)	0.0273 (5)	0.0284 (5)	−0.0056 (3)	−0.0051 (3)	0.0043 (3)
O2	0.0295 (5)	0.0440 (6)	0.0286 (5)	−0.0172 (4)	−0.0069 (4)	0.0092 (4)
O3	0.0225 (4)	0.0322 (5)	0.0255 (5)	−0.0019 (3)	−0.0021 (3)	0.0050 (3)
O4	0.0273 (5)	0.0335 (5)	0.0288 (5)	−0.0079 (4)	0.0006 (4)	0.0073 (4)
N1	0.0259 (5)	0.0269 (5)	0.0270 (5)	−0.0052 (4)	0.0023 (4)	0.0023 (4)
N2	0.0216 (5)	0.0240 (5)	0.0250 (5)	−0.0040 (4)	−0.0032 (4)	0.0040 (4)
C1	0.0204 (5)	0.0287 (6)	0.0253 (6)	−0.0024 (5)	−0.0026 (4)	0.0029 (5)
C2	0.0275 (6)	0.0296 (6)	0.0274 (6)	−0.0025 (5)	−0.0030 (5)	0.0078 (5)
C3	0.0204 (6)	0.0312 (7)	0.0328 (7)	−0.0041 (5)	0.0014 (5)	0.0034 (5)
C4	0.0211 (6)	0.0276 (6)	0.0285 (6)	−0.0019 (5)	−0.0023 (5)	0.0042 (5)
C5	0.0207 (5)	0.0200 (5)	0.0208 (5)	−0.0009 (4)	0.0015 (4)	−0.0012 (4)
C6	0.0194 (5)	0.0202 (5)	0.0210 (5)	−0.0006 (4)	0.0008 (4)	−0.0023 (4)
C7	0.0188 (5)	0.0262 (6)	0.0240 (6)	−0.0018 (4)	0.0005 (4)	0.0013 (5)
C8	0.0274 (6)	0.0391 (7)	0.0257 (6)	−0.0108 (5)	−0.0046 (5)	0.0020 (5)
C9	0.0302 (7)	0.0436 (8)	0.0223 (6)	−0.0093 (6)	−0.0022 (5)	0.0058 (5)
C10	0.0202 (5)	0.0263 (6)	0.0273 (6)	−0.0016 (4)	0.0024 (4)	0.0030 (5)
C11	0.0254 (6)	0.0328 (7)	0.0269 (6)	−0.0080 (5)	−0.0028 (5)	0.0012 (5)
C12	0.0249 (6)	0.0338 (7)	0.0226 (6)	−0.0051 (5)	−0.0031 (5)	0.0041 (5)
C13	0.0193 (5)	0.0268 (6)	0.0247 (6)	−0.0005 (5)	−0.0008 (4)	0.0014 (5)
C14	0.0422 (8)	0.0549 (9)	0.0320 (7)	−0.0171 (7)	−0.0017 (6)	0.0162 (7)

Geometric parameters (Å, º)

O1—C6	1.2358 (14)	C4—C5	1.3876 (16)
O2—C13	1.3214 (14)	C4—H4A	0.9500
O2—H1O2	0.97 (2)	C5—C6	1.5084 (16)
O3—C13	1.2229 (14)	C7—C8	1.3911 (17)
O4—C10	1.3664 (14)	C7—C12	1.3917 (16)
O4—C14	1.4203 (16)	C7—C13	1.4833 (16)
N1—C3	1.3359 (16)	C8—C9	1.3916 (18)
N1—C2	1.3383 (16)	C8—H8A	0.9500
N2—C6	1.3284 (15)	C9—C10	1.3901 (17)
N2—H1N2	0.910 (17)	C9—H9A	0.9500
N2—H2N2	0.906 (16)	C10—C11	1.3856 (17)
C1—C2	1.3803 (18)	C11—C12	1.3822 (18)
C1—C5	1.3870 (16)	C11—H11A	0.9500
C1—H1A	0.9500	C12—H12A	0.9500
C2—H2A	0.9500	C14—H14A	0.9800
C3—C4	1.3883 (17)	C14—H14B	0.9800
C3—H3A	0.9500	C14—H14C	0.9800
C13—O2—H1O2	111.4 (12)	C12—C7—C13	119.24 (10)
C10—O4—C14	117.69 (10)	C7—C8—C9	120.94 (12)
C3—N1—C2	117.66 (11)	C7—C8—H8A	119.5
C6—N2—H1N2	116.6 (10)	C9—C8—H8A	119.5
C6—N2—H2N2	124.7 (10)	C10—C9—C8	119.35 (12)
H1N2—N2—H2N2	118.6 (14)	C10—C9—H9A	120.3
C2—C1—C5	119.02 (11)	C8—C9—H9A	120.3
C2—C1—H1A	120.5	O4—C10—C11	115.06 (11)
C5—C1—H1A	120.5	O4—C10—C9	124.82 (11)
N1—C2—C1	123.14 (12)	C11—C10—C9	120.12 (11)
N1—C2—H2A	118.4	C12—C11—C10	120.07 (11)
C1—C2—H2A	118.4	C12—C11—H11A	120.0
N1—C3—C4	123.10 (11)	C10—C11—H11A	120.0
N1—C3—H3A	118.4	C11—C12—C7	120.76 (11)
C4—C3—H3A	118.4	C11—C12—H12A	119.6
C5—C4—C3	118.72 (11)	C7—C12—H12A	119.6
C5—C4—H4A	120.6	O3—C13—O2	122.45 (11)
C3—C4—H4A	120.6	O3—C13—C7	123.22 (11)
C1—C5—C4	118.34 (11)	O2—C13—C7	114.31 (10)
C1—C5—C6	117.36 (10)	O4—C14—H14A	109.5
C4—C5—C6	124.26 (10)	O4—C14—H14B	109.5
O1—C6—N2	122.99 (11)	H14A—C14—H14B	109.5
O1—C6—C5	118.30 (10)	O4—C14—H14C	109.5
N2—C6—C5	118.68 (10)	H14A—C14—H14C	109.5
C8—C7—C12	118.74 (11)	H14B—C14—H14C	109.5
C8—C7—C13	122.02 (11)
C3—N1—C2—C1	1.0 (2)	C7—C8—C9—C10	0.6 (2)
C5—C1—C2—N1	0.0 (2)	C14—O4—C10—C11	−177.37 (13)
C2—N1—C3—C4	−1.41 (19)	C14—O4—C10—C9	1.93 (19)
N1—C3—C4—C5	0.74 (19)	C8—C9—C10—O4	179.22 (12)
C2—C1—C5—C4	−0.67 (18)	C8—C9—C10—C11	−1.5 (2)
C2—C1—C5—C6	177.14 (11)	O4—C10—C11—C12	−179.69 (12)
C3—C4—C5—C1	0.33 (18)	C9—C10—C11—C12	1.0 (2)
C3—C4—C5—C6	−177.31 (11)	C10—C11—C12—C7	0.5 (2)
C1—C5—C6—O1	−5.10 (16)	C8—C7—C12—C11	−1.4 (2)
C4—C5—C6—O1	172.57 (12)	C13—C7—C12—C11	178.23 (12)
C1—C5—C6—N2	176.75 (11)	C8—C7—C13—O3	−174.03 (12)
C4—C5—C6—N2	−5.58 (17)	C12—C7—C13—O3	6.31 (19)
C12—C7—C8—C9	0.9 (2)	C8—C7—C13—O2	7.33 (18)
C13—C7—C8—C9	−178.77 (12)	C12—C7—C13—O2	−172.33 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N1	0.97 (2)	1.68 (2)	2.6447 (15)	179 (2)
N2—H1N2···O1^i	0.912 (16)	1.966 (16)	2.8720 (14)	171.8 (14)
N2—H2N2···O3^ii	0.907 (16)	2.035 (16)	2.9301 (13)	168.8 (14)
C4—H4A···O3^ii	0.95	2.53	3.4262 (15)	158
C11—H11A···O1^iii	0.95	2.51	3.1256 (15)	123
C14—H14A···O4^iv	0.98	2.56	3.4985 (19)	160

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

(mo_in4meo200_0m) Isonicotinamide 4-methoxybenzoic acid

Crystal data

C8H8O3·C6H6N2O	F(000) = 1152
Mr = 274.27	Dx = 1.381 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 20.126 (5) Å	Cell parameters from 2724 reflections
b = 5.2212 (12) Å	θ = 2.5–25.7°
c = 25.134 (6) Å	µ = 0.10 mm^−1
β = 92.401 (16)°	T = 200 K
V = 2638.8 (11) Å^3	Block, colourless
Z = 8	0.81 × 0.13 × 0.05 mm

Data collection

Bruker APEX Duo CCD area detector diffractometer	3259 independent reflections
Radiation source: fine-focus sealed tube	2204 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ and ω scans	θmax = 28.3°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −26→26
Tmin = 0.660, Tmax = 0.969	k = −6→6
14445 measured reflections	l = −33→33

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.145	w = 1/[σ^2(Fo^2) + (0.0834P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
3259 reflections	Δρmax = 0.27 e Å^−3
194 parameters	Δρmin = −0.21 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.

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

	x	y	z	Uiso*/Ueq
O1	1.00083 (5)	1.2458 (2)	0.54443 (4)	0.0349 (3)
O2	0.76788 (6)	0.2659 (2)	0.65543 (5)	0.0454 (4)
H1O2	0.7929 (11)	0.388 (4)	0.6357 (8)	0.072 (7)*
O3	0.70561 (5)	0.2434 (2)	0.58023 (4)	0.0362 (3)
O4	0.56217 (6)	−0.5834 (2)	0.72070 (4)	0.0401 (3)
N1	0.83840 (7)	0.5992 (3)	0.60167 (5)	0.0354 (3)
N2	0.91625 (7)	1.3338 (3)	0.48579 (5)	0.0318 (3)
H1N2	0.9407 (9)	1.468 (3)	0.4737 (6)	0.040 (5)*
H2N2	0.8760 (10)	1.299 (3)	0.4698 (7)	0.042 (5)*
C1	0.93706 (8)	0.8404 (3)	0.58908 (6)	0.0331 (4)
H1A	0.9825	0.8703	0.5988	0.040*
C2	0.90219 (8)	0.6512 (3)	0.61395 (6)	0.0379 (4)
H2A	0.9245	0.5533	0.6411	0.045*
C3	0.80810 (8)	0.7371 (3)	0.56329 (7)	0.0371 (4)
H3A	0.7629	0.7002	0.5539	0.044*
C4	0.83928 (7)	0.9321 (3)	0.53640 (6)	0.0346 (4)
H4A	0.8158	1.0267	0.5093	0.042*
C5	0.90531 (7)	0.9866 (3)	0.54978 (5)	0.0271 (3)
C6	0.94444 (7)	1.1996 (3)	0.52556 (6)	0.0269 (3)
C7	0.67704 (7)	−0.0196 (3)	0.65336 (6)	0.0305 (3)
C8	0.68753 (8)	−0.0766 (3)	0.70678 (6)	0.0406 (4)
H8A	0.7209	0.0131	0.7271	0.049*
C9	0.65007 (9)	−0.2630 (3)	0.73122 (6)	0.0422 (4)
H9A	0.6575	−0.2995	0.7680	0.051*
C10	0.60180 (7)	−0.3951 (3)	0.70145 (6)	0.0331 (4)
C11	0.59033 (8)	−0.3371 (3)	0.64818 (6)	0.0383 (4)
H11A	0.5568	−0.4262	0.6279	0.046*
C12	0.62742 (8)	−0.1501 (3)	0.62442 (6)	0.0365 (4)
H12A	0.6189	−0.1103	0.5879	0.044*
C13	0.71712 (7)	0.1748 (3)	0.62616 (6)	0.0317 (4)
C14	0.56967 (10)	−0.6453 (4)	0.77556 (7)	0.0577 (6)
H14A	0.5403	−0.7887	0.7836	0.087*
H14B	0.5579	−0.4962	0.7969	0.087*
H14C	0.6159	−0.6937	0.7841	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0280 (6)	0.0367 (6)	0.0393 (6)	−0.0082 (5)	−0.0089 (5)	0.0063 (5)
O2	0.0391 (7)	0.0578 (8)	0.0381 (7)	−0.0232 (6)	−0.0116 (5)	0.0126 (6)
O3	0.0301 (6)	0.0439 (7)	0.0342 (6)	−0.0032 (5)	−0.0058 (5)	0.0066 (5)
O4	0.0353 (6)	0.0448 (7)	0.0400 (6)	−0.0104 (5)	−0.0010 (5)	0.0095 (5)
N1	0.0337 (8)	0.0361 (7)	0.0364 (7)	−0.0063 (6)	0.0015 (6)	0.0032 (6)
N2	0.0280 (7)	0.0325 (7)	0.0341 (7)	−0.0056 (6)	−0.0063 (6)	0.0057 (6)
C1	0.0268 (8)	0.0376 (8)	0.0344 (8)	−0.0035 (7)	−0.0049 (6)	0.0052 (7)
C2	0.0355 (9)	0.0405 (9)	0.0371 (9)	−0.0027 (7)	−0.0061 (7)	0.0091 (7)
C3	0.0260 (8)	0.0410 (9)	0.0438 (10)	−0.0061 (7)	−0.0016 (7)	0.0047 (7)
C4	0.0265 (8)	0.0362 (8)	0.0407 (9)	−0.0019 (6)	−0.0054 (6)	0.0069 (7)
C5	0.0257 (8)	0.0270 (7)	0.0286 (7)	−0.0004 (6)	−0.0002 (6)	−0.0011 (6)
C6	0.0242 (7)	0.0279 (7)	0.0286 (7)	−0.0007 (6)	−0.0008 (6)	−0.0024 (6)
C7	0.0247 (8)	0.0357 (8)	0.0309 (8)	−0.0013 (6)	−0.0019 (6)	0.0010 (6)
C8	0.0345 (9)	0.0523 (10)	0.0343 (9)	−0.0128 (8)	−0.0084 (7)	0.0034 (7)
C9	0.0388 (10)	0.0574 (11)	0.0300 (9)	−0.0122 (8)	−0.0051 (7)	0.0072 (7)
C10	0.0278 (8)	0.0345 (8)	0.0368 (8)	−0.0014 (7)	0.0017 (6)	0.0035 (6)
C11	0.0333 (9)	0.0437 (9)	0.0372 (9)	−0.0102 (7)	−0.0059 (7)	0.0008 (7)
C12	0.0323 (9)	0.0452 (9)	0.0312 (8)	−0.0067 (7)	−0.0066 (6)	0.0057 (7)
C13	0.0246 (8)	0.0367 (8)	0.0334 (8)	−0.0004 (6)	−0.0039 (6)	0.0014 (7)
C14	0.0573 (13)	0.0724 (14)	0.0431 (10)	−0.0201 (11)	−0.0030 (9)	0.0201 (10)

Geometric parameters (Å, º)

O1—C6	1.2355 (17)	C4—C5	1.386 (2)
O2—C13	1.3222 (18)	C4—H4A	0.9500
O2—H1O2	0.96 (2)	C5—C6	1.506 (2)
O3—C13	1.2218 (17)	C7—C8	1.383 (2)
O4—C10	1.3672 (18)	C7—C12	1.389 (2)
O4—C14	1.418 (2)	C7—C13	1.481 (2)
N1—C3	1.331 (2)	C8—C9	1.390 (2)
N1—C2	1.336 (2)	C8—H8A	0.9500
N2—C6	1.3284 (19)	C9—C10	1.385 (2)
N2—H1N2	0.917 (18)	C9—H9A	0.9500
N2—H2N2	0.91 (2)	C10—C11	1.382 (2)
C1—C2	1.377 (2)	C11—C12	1.380 (2)
C1—C5	1.384 (2)	C11—H11A	0.9500
C1—H1A	0.9500	C12—H12A	0.9500
C2—H2A	0.9500	C14—H14A	0.9800
C3—C4	1.386 (2)	C14—H14B	0.9800
C3—H3A	0.9500	C14—H14C	0.9800
C13—O2—H1O2	111.1 (12)	C12—C7—C13	119.21 (13)
C10—O4—C14	117.90 (13)	C7—C8—C9	121.08 (15)
C3—N1—C2	117.64 (14)	C7—C8—H8A	119.5
C6—N2—H1N2	115.9 (10)	C9—C8—H8A	119.5
C6—N2—H2N2	124.8 (12)	C10—C9—C8	119.42 (15)
H1N2—N2—H2N2	119.3 (16)	C10—C9—H9A	120.3
C2—C1—C5	119.40 (15)	C8—C9—H9A	120.3
C2—C1—H1A	120.3	O4—C10—C11	115.08 (14)
C5—C1—H1A	120.3	O4—C10—C9	124.98 (14)
N1—C2—C1	122.99 (15)	C11—C10—C9	119.93 (14)
N1—C2—H2A	118.5	C12—C11—C10	120.17 (14)
C1—C2—H2A	118.5	C12—C11—H11A	119.9
N1—C3—C4	123.20 (15)	C10—C11—H11A	119.9
N1—C3—H3A	118.4	C11—C12—C7	120.70 (14)
C4—C3—H3A	118.4	C11—C12—H12A	119.6
C3—C4—C5	118.76 (14)	C7—C12—H12A	119.6
C3—C4—H4A	120.6	O3—C13—O2	122.12 (14)
C5—C4—H4A	120.6	O3—C13—C7	123.49 (13)
C1—C5—C4	117.99 (14)	O2—C13—C7	114.38 (13)
C1—C5—C6	117.54 (13)	O4—C14—H14A	109.5
C4—C5—C6	124.45 (13)	O4—C14—H14B	109.5
O1—C6—N2	122.84 (14)	H14A—C14—H14B	109.5
O1—C6—C5	118.47 (13)	O4—C14—H14C	109.5
N2—C6—C5	118.67 (13)	H14A—C14—H14C	109.5
C8—C7—C12	118.67 (14)	H14B—C14—H14C	109.5
C8—C7—C13	122.12 (14)
C3—N1—C2—C1	0.5 (3)	C7—C8—C9—C10	0.5 (3)
C5—C1—C2—N1	0.5 (3)	C14—O4—C10—C11	−177.65 (16)
C2—N1—C3—C4	−0.9 (2)	C14—O4—C10—C9	1.5 (2)
N1—C3—C4—C5	0.3 (2)	C8—C9—C10—O4	179.50 (16)
C2—C1—C5—C4	−1.1 (2)	C8—C9—C10—C11	−1.3 (3)
C2—C1—C5—C6	177.09 (14)	O4—C10—C11—C12	−179.96 (15)
C3—C4—C5—C1	0.8 (2)	C9—C10—C11—C12	0.8 (3)
C3—C4—C5—C6	−177.33 (14)	C10—C11—C12—C7	0.6 (3)
C1—C5—C6—O1	−5.3 (2)	C8—C7—C12—C11	−1.5 (3)
C4—C5—C6—O1	172.84 (15)	C13—C7—C12—C11	178.29 (15)
C1—C5—C6—N2	176.45 (14)	C8—C7—C13—O3	−174.03 (16)
C4—C5—C6—N2	−5.5 (2)	C12—C7—C13—O3	6.2 (2)
C12—C7—C8—C9	0.9 (3)	C8—C7—C13—O2	7.3 (2)
C13—C7—C8—C9	−178.83 (15)	C12—C7—C13—O2	−172.44 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N1	0.96 (2)	1.69 (2)	2.651 (2)	179 (2)
N2—H1N2···O1^i	0.915 (17)	1.967 (17)	2.879 (2)	173.4 (14)
N2—H2N2···O3^ii	0.908 (19)	2.047 (19)	2.9411 (18)	168.2 (16)
C4—H4A···O3^ii	0.95	2.54	3.439 (2)	158
C11—H11A···O1^iii	0.95	2.52	3.143 (2)	123
C14—H14A···O4^iv	0.98	2.57	3.508 (2)	160

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

(mo_in4meo250_0m) Isonicotinamide 4-methoxybenzoic acid

Crystal data

C8H8O3·C6H6N2O	F(000) = 1152
Mr = 274.27	Dx = 1.374 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 20.161 (4) Å	Cell parameters from 2401 reflections
b = 5.2180 (11) Å	θ = 2.5–25.6°
c = 25.234 (5) Å	µ = 0.10 mm^−1
β = 92.559 (14)°	T = 250 K
V = 2652.0 (9) Å^3	Block, colourless
Z = 8	0.81 × 0.13 × 0.05 mm

Data collection

Bruker APEX Duo CCD area detector diffractometer	3225 independent reflections
Radiation source: fine-focus sealed tube	2102 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
φ and ω scans	θmax = 28.1°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −26→24
Tmin = 0.836, Tmax = 0.969	k = −6→6
14256 measured reflections	l = −33→33

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.147	w = 1/[σ^2(Fo^2) + (0.0819P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
3225 reflections	Δρmax = 0.23 e Å^−3
194 parameters	Δρmin = −0.18 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.

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

	x	y	z	Uiso*/Ueq
O1	1.00048 (5)	1.2464 (2)	0.54466 (4)	0.0426 (3)
O2	0.76769 (6)	0.2665 (3)	0.65495 (5)	0.0551 (4)
H1O2	0.7959 (12)	0.379 (5)	0.6360 (9)	0.095 (8)*
O3	0.70544 (6)	0.2435 (2)	0.58019 (4)	0.0443 (3)
O4	0.56250 (6)	−0.5795 (2)	0.72084 (5)	0.0502 (3)
N1	0.83831 (7)	0.6007 (3)	0.60153 (5)	0.0434 (4)
N2	0.91633 (7)	1.3329 (3)	0.48603 (5)	0.0385 (3)
H1N2	0.9405 (9)	1.460 (3)	0.4738 (6)	0.044 (5)*
H2N2	0.8752 (10)	1.303 (4)	0.4707 (7)	0.048 (5)*
C1	0.93672 (8)	0.8421 (3)	0.58919 (6)	0.0411 (4)
H1A	0.9815	0.8723	0.5991	0.049*
C2	0.90180 (9)	0.6525 (4)	0.61371 (7)	0.0463 (4)
H2A	0.9239	0.5548	0.6404	0.056*
C3	0.80829 (9)	0.7381 (3)	0.56308 (7)	0.0462 (4)
H3A	0.7637	0.7014	0.5535	0.055*
C4	0.83969 (8)	0.9331 (3)	0.53643 (7)	0.0421 (4)
H4A	0.8166	1.0267	0.5096	0.050*
C5	0.90527 (7)	0.9872 (3)	0.54988 (5)	0.0324 (3)
C6	0.94449 (7)	1.2004 (3)	0.52571 (6)	0.0323 (3)
C7	0.67698 (7)	−0.0184 (3)	0.65318 (6)	0.0367 (4)
C8	0.68781 (9)	−0.0748 (4)	0.70636 (7)	0.0494 (5)
H8A	0.7210	0.0137	0.7263	0.059*
C9	0.65040 (9)	−0.2600 (4)	0.73087 (7)	0.0506 (5)
H9A	0.6579	−0.2957	0.7672	0.061*
C10	0.60205 (8)	−0.3914 (3)	0.70139 (6)	0.0396 (4)
C11	0.59047 (9)	−0.3342 (4)	0.64857 (7)	0.0463 (4)
H11A	0.5572	−0.4224	0.6286	0.056*
C12	0.62732 (8)	−0.1484 (4)	0.62478 (6)	0.0451 (4)
H12A	0.6186	−0.1094	0.5888	0.054*
C13	0.71710 (8)	0.1754 (3)	0.62590 (6)	0.0375 (4)
C14	0.57026 (11)	−0.6410 (5)	0.77532 (8)	0.0715 (7)
H14A	0.5428	−0.7880	0.7830	0.107*
H14B	0.5568	−0.4959	0.7963	0.107*
H14C	0.6164	−0.6814	0.7840	0.107*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0362 (6)	0.0430 (7)	0.0475 (7)	−0.0101 (5)	−0.0105 (5)	0.0084 (5)
O2	0.0490 (8)	0.0692 (9)	0.0458 (7)	−0.0268 (7)	−0.0112 (6)	0.0140 (6)
O3	0.0393 (7)	0.0519 (7)	0.0409 (7)	−0.0039 (5)	−0.0050 (5)	0.0097 (5)
O4	0.0466 (7)	0.0538 (7)	0.0500 (7)	−0.0136 (6)	0.0006 (5)	0.0110 (6)
N1	0.0426 (8)	0.0422 (8)	0.0456 (8)	−0.0071 (6)	0.0025 (6)	0.0032 (6)
N2	0.0351 (8)	0.0382 (8)	0.0414 (8)	−0.0060 (6)	−0.0066 (6)	0.0068 (6)
C1	0.0355 (9)	0.0449 (9)	0.0424 (9)	−0.0047 (7)	−0.0055 (7)	0.0070 (7)
C2	0.0455 (10)	0.0477 (10)	0.0448 (9)	−0.0040 (8)	−0.0063 (7)	0.0122 (8)
C3	0.0329 (9)	0.0491 (10)	0.0565 (11)	−0.0080 (8)	−0.0010 (8)	0.0072 (8)
C4	0.0363 (9)	0.0418 (9)	0.0473 (9)	−0.0027 (7)	−0.0057 (7)	0.0083 (8)
C5	0.0326 (8)	0.0302 (8)	0.0342 (8)	−0.0006 (6)	0.0006 (6)	−0.0019 (6)
C6	0.0315 (8)	0.0316 (8)	0.0338 (8)	−0.0011 (6)	−0.0004 (6)	−0.0021 (6)
C7	0.0312 (8)	0.0411 (9)	0.0377 (8)	−0.0012 (7)	−0.0016 (6)	0.0023 (7)
C8	0.0448 (10)	0.0602 (11)	0.0423 (10)	−0.0167 (9)	−0.0085 (7)	0.0054 (8)
C9	0.0498 (11)	0.0662 (12)	0.0351 (9)	−0.0129 (9)	−0.0054 (8)	0.0106 (8)
C10	0.0337 (8)	0.0418 (9)	0.0435 (9)	−0.0025 (7)	0.0036 (7)	0.0046 (7)
C11	0.0416 (9)	0.0540 (10)	0.0426 (9)	−0.0147 (8)	−0.0075 (7)	0.0011 (8)
C12	0.0431 (10)	0.0551 (10)	0.0365 (9)	−0.0096 (8)	−0.0061 (7)	0.0061 (8)
C13	0.0321 (8)	0.0409 (9)	0.0391 (9)	−0.0012 (7)	−0.0027 (6)	0.0027 (7)
C14	0.0732 (15)	0.0856 (16)	0.0554 (12)	−0.0237 (13)	0.0001 (10)	0.0252 (11)

Geometric parameters (Å, º)

O1—C6	1.2298 (18)	C4—C5	1.379 (2)
O2—C13	1.3179 (19)	C4—H4A	0.9400
O2—H1O2	0.96 (3)	C5—C6	1.509 (2)
O3—C13	1.2197 (18)	C7—C8	1.382 (2)
O4—C10	1.3691 (19)	C7—C12	1.383 (2)
O4—C14	1.414 (2)	C7—C13	1.483 (2)
N1—C3	1.330 (2)	C8—C9	1.388 (2)
N1—C2	1.331 (2)	C8—H8A	0.9400
N2—C6	1.324 (2)	C9—C10	1.382 (2)
N2—H1N2	0.889 (18)	C9—H9A	0.9400
N2—H2N2	0.912 (19)	C10—C11	1.376 (2)
C1—C2	1.377 (2)	C11—C12	1.375 (2)
C1—C5	1.380 (2)	C11—H11A	0.9400
C1—H1A	0.9400	C12—H12A	0.9400
C2—H2A	0.9400	C14—H14A	0.9700
C3—C4	1.388 (2)	C14—H14B	0.9700
C3—H3A	0.9400	C14—H14C	0.9700
C13—O2—H1O2	113.9 (13)	C12—C7—C13	119.42 (14)
C10—O4—C14	118.06 (14)	C7—C8—C9	121.04 (16)
C3—N1—C2	117.43 (14)	C7—C8—H8A	119.5
C6—N2—H1N2	115.5 (11)	C9—C8—H8A	119.5
C6—N2—H2N2	125.7 (12)	C10—C9—C8	119.34 (15)
H1N2—N2—H2N2	118.8 (16)	C10—C9—H9A	120.3
C2—C1—C5	119.32 (16)	C8—C9—H9A	120.3
C2—C1—H1A	120.3	O4—C10—C11	115.26 (15)
C5—C1—H1A	120.3	O4—C10—C9	124.82 (15)
N1—C2—C1	123.22 (16)	C11—C10—C9	119.92 (15)
N1—C2—H2A	118.4	C12—C11—C10	120.30 (15)
C1—C2—H2A	118.4	C12—C11—H11A	119.9
N1—C3—C4	123.09 (16)	C10—C11—H11A	119.9
N1—C3—H3A	118.5	C11—C12—C7	120.82 (15)
C4—C3—H3A	118.5	C11—C12—H12A	119.6
C5—C4—C3	118.94 (15)	C7—C12—H12A	119.6
C5—C4—H4A	120.5	O3—C13—O2	122.18 (14)
C3—C4—H4A	120.5	O3—C13—C7	123.46 (14)
C4—C5—C1	117.98 (14)	O2—C13—C7	114.35 (13)
C4—C5—C6	124.43 (14)	O4—C14—H14A	109.5
C1—C5—C6	117.57 (14)	O4—C14—H14B	109.5
O1—C6—N2	123.19 (14)	H14A—C14—H14B	109.5
O1—C6—C5	118.38 (13)	O4—C14—H14C	109.5
N2—C6—C5	118.41 (14)	H14A—C14—H14C	109.5
C8—C7—C12	118.56 (15)	H14B—C14—H14C	109.5
C8—C7—C13	122.02 (14)
C3—N1—C2—C1	1.1 (3)	C7—C8—C9—C10	0.6 (3)
C5—C1—C2—N1	−0.2 (3)	C14—O4—C10—C11	−177.76 (18)
C2—N1—C3—C4	−1.3 (3)	C14—O4—C10—C9	1.6 (3)
N1—C3—C4—C5	0.5 (3)	C8—C9—C10—O4	179.32 (17)
C3—C4—C5—C1	0.5 (2)	C8—C9—C10—C11	−1.4 (3)
C3—C4—C5—C6	−177.43 (14)	O4—C10—C11—C12	−179.93 (16)
C2—C1—C5—C4	−0.7 (2)	C9—C10—C11—C12	0.7 (3)
C2—C1—C5—C6	177.42 (15)	C10—C11—C12—C7	0.7 (3)
C4—C5—C6—O1	172.79 (15)	C8—C7—C12—C11	−1.5 (3)
C1—C5—C6—O1	−5.2 (2)	C13—C7—C12—C11	178.20 (16)
C4—C5—C6—N2	−5.5 (2)	C8—C7—C13—O3	−174.12 (17)
C1—C5—C6—N2	176.48 (15)	C12—C7—C13—O3	6.2 (3)
C12—C7—C8—C9	0.8 (3)	C8—C7—C13—O2	7.0 (2)
C13—C7—C8—C9	−178.89 (16)	C12—C7—C13—O2	−172.70 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N1	0.96 (2)	1.70 (2)	2.656 (2)	174 (2)
N2—H1N2···O1^i	0.887 (17)	2.007 (17)	2.8892 (19)	173.0 (14)
N2—H2N2···O3^ii	0.91 (2)	2.050 (19)	2.9446 (19)	166.3 (17)
C4—H4A···O3^ii	0.94	2.55	3.446 (2)	158
C11—H11A···O1^iii	0.94	2.53	3.155 (2)	124

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

(in4meo3_0m) Isonicotinamide 4-methoxybenzoic acid

Crystal data

C8H8O3·C6H6N2O	F(000) = 1152
Mr = 274.27	Dx = 1.362 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 20.246 (2) Å	Cell parameters from 3766 reflections
b = 5.2132 (6) Å	θ = 2.5–28.1°
c = 25.372 (2) Å	µ = 0.10 mm^−1
β = 92.557 (7)°	T = 300 K
V = 2675.3 (5) Å^3	Block, colourless
Z = 8	0.81 × 0.13 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	3250 independent reflections
Radiation source: fine-focus sealed tube	2302 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 28.1°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −25→26
Tmin = 0.881, Tmax = 0.969	k = −6→6
15047 measured reflections	l = −33→33

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.150	w = 1/[σ^2(Fo^2) + (0.0765P)^2 + 0.7198P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
3250 reflections	Δρmax = 0.20 e Å^−3
194 parameters	Δρmin = −0.23 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.

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

	x	y	z	Uiso*/Ueq
O1	1.00017 (5)	1.2472 (2)	0.54473 (5)	0.0522 (3)
O2	0.76761 (6)	0.2674 (3)	0.65442 (5)	0.0665 (4)
H1O2	0.7957 (12)	0.386 (5)	0.6355 (9)	0.104 (8)*
O3	0.70521 (6)	0.2440 (2)	0.58033 (4)	0.0541 (3)
O4	0.56284 (6)	−0.5750 (3)	0.72112 (5)	0.0622 (4)
N1	0.83835 (7)	0.6021 (3)	0.60128 (5)	0.0519 (4)
N2	0.91656 (7)	1.3329 (3)	0.48619 (5)	0.0470 (3)
H1N2	0.9399 (10)	1.468 (4)	0.4733 (7)	0.064 (5)*
H2N2	0.8758 (10)	1.298 (4)	0.4702 (8)	0.060 (5)*
C1	0.93642 (8)	0.8435 (3)	0.58920 (6)	0.0491 (4)
H1A	0.9805	0.8735	0.5990	0.059*
C2	0.90175 (9)	0.6541 (4)	0.61361 (7)	0.0554 (4)
H2A	0.9234	0.5578	0.6399	0.066*
C3	0.80879 (8)	0.7392 (3)	0.56299 (7)	0.0556 (4)
H3A	0.7649	0.7029	0.5536	0.067*
C4	0.83981 (8)	0.9333 (3)	0.53634 (7)	0.0508 (4)
H4A	0.8172	1.0250	0.5098	0.061*
C5	0.90535 (7)	0.9884 (3)	0.55007 (5)	0.0393 (3)
C6	0.94431 (7)	1.2003 (3)	0.52584 (6)	0.0392 (3)
C7	0.67715 (7)	−0.0166 (3)	0.65313 (6)	0.0453 (4)
C8	0.68810 (9)	−0.0724 (4)	0.70601 (7)	0.0601 (5)
H8A	0.7210	0.0150	0.7254	0.072*
C9	0.65077 (9)	−0.2566 (4)	0.73060 (7)	0.0626 (5)
H9A	0.6582	−0.2914	0.7663	0.075*
C10	0.60241 (8)	−0.3879 (3)	0.70155 (6)	0.0494 (4)
C11	0.59064 (9)	−0.3317 (4)	0.64895 (7)	0.0568 (4)
H11A	0.5577	−0.4189	0.6295	0.068*
C12	0.62746 (8)	−0.1469 (4)	0.62502 (7)	0.0541 (4)
H12A	0.6189	−0.1090	0.5896	0.065*
C13	0.71701 (7)	0.1766 (3)	0.62578 (6)	0.0458 (4)
C14	0.57079 (12)	−0.6368 (5)	0.77512 (9)	0.0875 (7)
H14A	0.5429	−0.7797	0.7829	0.131*
H14B	0.5587	−0.4917	0.7959	0.131*
H14C	0.6161	−0.6810	0.7834	0.131*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0455 (6)	0.0536 (7)	0.0563 (7)	−0.0124 (5)	−0.0110 (5)	0.0103 (5)
O2	0.0598 (8)	0.0831 (9)	0.0553 (8)	−0.0311 (7)	−0.0127 (6)	0.0175 (7)
O3	0.0488 (6)	0.0649 (7)	0.0481 (7)	−0.0058 (5)	−0.0052 (5)	0.0102 (5)
O4	0.0594 (7)	0.0675 (8)	0.0598 (8)	−0.0156 (6)	0.0030 (6)	0.0137 (6)
N1	0.0531 (8)	0.0522 (8)	0.0507 (8)	−0.0101 (6)	0.0047 (6)	0.0052 (6)
N2	0.0463 (8)	0.0478 (7)	0.0461 (8)	−0.0076 (6)	−0.0060 (6)	0.0082 (6)
C1	0.0446 (8)	0.0543 (9)	0.0478 (9)	−0.0060 (7)	−0.0044 (7)	0.0076 (7)
C2	0.0559 (10)	0.0579 (10)	0.0517 (10)	−0.0051 (8)	−0.0045 (7)	0.0141 (8)
C3	0.0427 (8)	0.0594 (10)	0.0645 (11)	−0.0096 (7)	0.0009 (8)	0.0091 (8)
C4	0.0431 (8)	0.0536 (9)	0.0552 (10)	−0.0044 (7)	−0.0043 (7)	0.0104 (8)
C5	0.0398 (7)	0.0393 (7)	0.0387 (8)	−0.0011 (6)	0.0022 (6)	−0.0024 (6)
C6	0.0391 (7)	0.0398 (7)	0.0386 (8)	−0.0021 (6)	−0.0005 (6)	−0.0015 (6)
C7	0.0394 (8)	0.0518 (9)	0.0445 (9)	−0.0027 (6)	−0.0003 (6)	0.0029 (7)
C8	0.0564 (10)	0.0740 (12)	0.0492 (10)	−0.0212 (9)	−0.0076 (8)	0.0052 (8)
C9	0.0620 (11)	0.0831 (13)	0.0420 (9)	−0.0163 (10)	−0.0055 (8)	0.0123 (9)
C10	0.0446 (8)	0.0526 (9)	0.0512 (9)	−0.0038 (7)	0.0049 (7)	0.0060 (7)
C11	0.0521 (9)	0.0665 (11)	0.0510 (10)	−0.0164 (8)	−0.0063 (7)	0.0027 (8)
C12	0.0521 (9)	0.0673 (11)	0.0424 (9)	−0.0112 (8)	−0.0062 (7)	0.0068 (8)
C13	0.0397 (8)	0.0527 (9)	0.0445 (9)	−0.0022 (7)	−0.0032 (6)	0.0036 (7)
C14	0.0902 (16)	0.1047 (18)	0.0674 (14)	−0.0305 (14)	0.0024 (11)	0.0290 (13)

Geometric parameters (Å, º)

O1—C6	1.2329 (17)	C4—C5	1.387 (2)
O2—C13	1.3172 (19)	C4—H4A	0.9300
O2—H1O2	0.98 (3)	C5—C6	1.505 (2)
O3—C13	1.2189 (18)	C7—C8	1.381 (2)
O4—C10	1.370 (2)	C7—C12	1.385 (2)
O4—C14	1.410 (2)	C7—C13	1.482 (2)
N1—C3	1.327 (2)	C8—C9	1.388 (2)
N1—C2	1.335 (2)	C8—H8A	0.9300
N2—C6	1.3248 (19)	C9—C10	1.381 (2)
N2—H1N2	0.92 (2)	C9—H9A	0.9300
N2—H2N2	0.92 (2)	C10—C11	1.377 (2)
C1—C2	1.375 (2)	C11—C12	1.376 (2)
C1—C5	1.377 (2)	C11—H11A	0.9300
C1—H1A	0.9300	C12—H12A	0.9300
C2—H2A	0.9300	C14—H14A	0.9600
C3—C4	1.383 (2)	C14—H14B	0.9600
C3—H3A	0.9300	C14—H14C	0.9600
C13—O2—H1O2	114.2 (14)	C12—C7—C13	119.35 (14)
C10—O4—C14	118.15 (15)	C7—C8—C9	121.04 (16)
C3—N1—C2	117.36 (14)	C7—C8—H8A	119.5
C6—N2—H1N2	117.7 (12)	C9—C8—H8A	119.5
C6—N2—H2N2	125.0 (12)	C10—C9—C8	119.38 (16)
H1N2—N2—H2N2	117.3 (17)	C10—C9—H9A	120.3
C2—C1—C5	119.52 (15)	C8—C9—H9A	120.3
C2—C1—H1A	120.2	O4—C10—C11	115.11 (15)
C5—C1—H1A	120.2	O4—C10—C9	124.88 (15)
N1—C2—C1	123.03 (16)	C11—C10—C9	120.01 (15)
N1—C2—H2A	118.5	C12—C11—C10	120.21 (15)
C1—C2—H2A	118.5	C12—C11—H11A	119.9
N1—C3—C4	123.52 (15)	C10—C11—H11A	119.9
N1—C3—H3A	118.2	C11—C12—C7	120.76 (15)
C4—C3—H3A	118.2	C11—C12—H12A	119.6
C3—C4—C5	118.60 (15)	C7—C12—H12A	119.6
C3—C4—H4A	120.7	O3—C13—O2	122.21 (14)
C5—C4—H4A	120.7	O3—C13—C7	123.44 (14)
C1—C5—C4	117.95 (14)	O2—C13—C7	114.34 (13)
C1—C5—C6	117.80 (13)	O4—C14—H14A	109.5
C4—C5—C6	124.23 (14)	O4—C14—H14B	109.5
O1—C6—N2	122.84 (14)	H14A—C14—H14B	109.5
O1—C6—C5	118.39 (13)	O4—C14—H14C	109.5
N2—C6—C5	118.75 (13)	H14A—C14—H14C	109.5
C8—C7—C12	118.59 (15)	H14B—C14—H14C	109.5
C8—C7—C13	122.06 (14)
C3—N1—C2—C1	1.1 (3)	C7—C8—C9—C10	0.7 (3)
C5—C1—C2—N1	−0.1 (3)	C14—O4—C10—C11	−178.06 (19)
C2—N1—C3—C4	−1.2 (3)	C14—O4—C10—C9	1.2 (3)
N1—C3—C4—C5	0.1 (3)	C8—C9—C10—O4	179.40 (18)
C2—C1—C5—C4	−1.0 (2)	C8—C9—C10—C11	−1.4 (3)
C2—C1—C5—C6	177.70 (15)	O4—C10—C11—C12	−179.96 (17)
C3—C4—C5—C1	0.9 (2)	C9—C10—C11—C12	0.7 (3)
C3—C4—C5—C6	−177.63 (14)	C10—C11—C12—C7	0.6 (3)
C1—C5—C6—O1	−5.5 (2)	C8—C7—C12—C11	−1.3 (3)
C4—C5—C6—O1	173.08 (15)	C13—C7—C12—C11	178.43 (17)
C1—C5—C6—N2	176.37 (14)	C8—C7—C13—O3	−174.11 (17)
C4—C5—C6—N2	−5.1 (2)	C12—C7—C13—O3	6.1 (3)
C12—C7—C8—C9	0.7 (3)	C8—C7—C13—O2	7.2 (2)
C13—C7—C8—C9	−179.08 (17)	C12—C7—C13—O2	−172.58 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···N1	0.98 (2)	1.68 (2)	2.662 (2)	175 (2)
N2—H1N2···O1^i	0.92 (2)	1.98 (2)	2.8927 (19)	171.0 (16)
N2—H2N2···O3^ii	0.92 (2)	2.06 (2)	2.9614 (18)	167.4 (18)
C4—H4A···O3^ii	0.93	2.58	3.461 (2)	159
C11—H11A···O1^iii	0.93	2.56	3.180 (2)	124

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