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Isonicotinamide–4-methoxybenzoic acid co-crystal (1), C
6H
6N
2O·C
8H
8O
3, 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
Tc = 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).
Supporting information
CCDC references: 1495125; 1495126; 1495127; 1495128; 1495129; 1495130; 1495131; 1495132
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
top
Crystal data top
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) Å3 | Plate, colourless |
Z = 8 | 0.55 × 0.19 × 0.05 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0675P)2 + 1.2363P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N2···O1i | 0.921 (16) | 1.996 (16) | 2.9033 (13) | 168.2 (13) |
N2—H2N2···O3ii | 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···O3ii | 0.95 | 2.46 | 3.3897 (14) | 166 |
C11—H11A···O1iii | 0.95 | 2.43 | 3.0724 (15) | 124 |
C14—H14A···O4iv | 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
top
Crystal data top
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) Å3 | Block, colourless |
Z = 8 | 0.81 × 0.13 × 0.05 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0688P)2 + 0.9686P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N2···O1i | 0.918 (16) | 1.998 (16) | 2.9062 (13) | 170.0 (14) |
N2—H2N2···O3ii | 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···O3ii | 0.95 | 2.46 | 3.3945 (15) | 166 |
C11—H11A···O1iii | 0.95 | 2.44 | 3.0791 (15) | 125 |
C14—H14A···O4iv | 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
top
Crystal data top
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) Å3 | Block, colourless |
Z = 8 | 0.81 × 0.13 × 0.05 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0729P)2 + 0.7112P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N2···O1i | 0.929 (19) | 1.980 (19) | 2.8992 (18) | 170.3 (15) |
N2—H2N2···O3ii | 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···O3ii | 0.95 | 2.46 | 3.393 (2) | 166 |
C11—H11A···O1iii | 0.95 | 2.44 | 3.074 (2) | 124 |
C14—H14A···O4iv | 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
top
Crystal data top
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) Å3 | Block, colourless |
Z = 8 | 0.81 × 0.13 × 0.05 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.134 | w = 1/[σ2(Fo2) + (0.0752P)2 + 0.3732P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O1i | 0.892 (17) | 1.990 (17) | 2.8744 (17) | 171.1 (16) |
N2—H2N2···O3ii | 0.933 (19) | 2.011 (19) | 2.9330 (17) | 169.6 (15) |
C4—H4A···O3ii | 0.95 | 2.53 | 3.429 (2) | 157 |
C11—H11A···O1iii | 0.95 | 2.51 | 3.127 (2) | 123 |
C14—H14A···O4iv | 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
top
Crystal data top
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) Å3 | Block, colourless |
Z = 8 | 0.81 × 0.13 × 0.05 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.0672P)2 + 0.9974P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O1i | 0.912 (16) | 1.966 (16) | 2.8720 (14) | 171.8 (14) |
N2—H2N2···O3ii | 0.907 (16) | 2.035 (16) | 2.9301 (13) | 168.8 (14) |
C4—H4A···O3ii | 0.95 | 2.53 | 3.4262 (15) | 158 |
C11—H11A···O1iii | 0.95 | 2.51 | 3.1256 (15) | 123 |
C14—H14A···O4iv | 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
top
Crystal data top
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) Å3 | Block, colourless |
Z = 8 | 0.81 × 0.13 × 0.05 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.145 | w = 1/[σ2(Fo2) + (0.0834P)2] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O1i | 0.915 (17) | 1.967 (17) | 2.879 (2) | 173.4 (14) |
N2—H2N2···O3ii | 0.908 (19) | 2.047 (19) | 2.9411 (18) | 168.2 (16) |
C4—H4A···O3ii | 0.95 | 2.54 | 3.439 (2) | 158 |
C11—H11A···O1iii | 0.95 | 2.52 | 3.143 (2) | 123 |
C14—H14A···O4iv | 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
top
Crystal data top
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) Å3 | Block, colourless |
Z = 8 | 0.81 × 0.13 × 0.05 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.147 | w = 1/[σ2(Fo2) + (0.0819P)2] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O1i | 0.887 (17) | 2.007 (17) | 2.8892 (19) | 173.0 (14) |
N2—H2N2···O3ii | 0.91 (2) | 2.050 (19) | 2.9446 (19) | 166.3 (17) |
C4—H4A···O3ii | 0.94 | 2.55 | 3.446 (2) | 158 |
C11—H11A···O1iii | 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
top
Crystal data top
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) Å3 | Block, colourless |
Z = 8 | 0.81 × 0.13 × 0.05 mm |
Data collection top
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 top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.150 | w = 1/[σ2(Fo2) + (0.0765P)2 + 0.7198P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O1i | 0.92 (2) | 1.98 (2) | 2.8927 (19) | 171.0 (16) |
N2—H2N2···O3ii | 0.92 (2) | 2.06 (2) | 2.9614 (18) | 167.4 (18) |
C4—H4A···O3ii | 0.93 | 2.58 | 3.461 (2) | 159 |
C11—H11A···O1iii | 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. |
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