Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028679/ob6584sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028679/ob6584Isup2.hkl |
CCDC reference: 287684
The compound (I) was prepared by the reaction of 2,3-dimethoxylphenylmethylidenemalononitrile (0.42 g, 2 mmol) and ethyl acetoacetate (0.39 g, 3 mmol) in the presence of triethylbenzylammonium chloride (0.1 g) in water at 363 K for 8 h (yield 93%, mp. 513–515 K). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a DMF solution.
1H NMR (CDCl3): 0.89 (t, J = 7.2 Hz, 3H, CH3), 2.68 (s, 3H, CH3), 3.86 (s, 3H, OCH3), 3.92 (s, 3H, OCH3), 4.00 (q, J = 7.2 Hz, 2H, CH2), 6.77 (dd, J = 1.2 Hz, J' = 7.6 Hz, 1H, ArH), 7.04 (dd, J = 1.2 Hz, J' = 8.0 Hz, 1H, ArH), 6.14 (dd, J = 7.6 Hz, J' = 8.0 Hz, 1H, ArH), IR (cm−1): 3052 (ArH), 2852 (C—H), 2224 (CN), 1722, 1661 (C=O), 1592, 1470, 1430 (phenyl ring).
The H atoms were positioned geometrically and refined as riding, with C—H = 0.93–0.97 Å and N—H = 0.86 Å, and with Uiso(H) = 1.2Ueq(parent atom).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
C18H18N2O5 | F(000) = 720 |
Mr = 342.34 | Dx = 1.323 Mg m−3 |
Monoclinic, P21/c | Melting point = 513–515 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 15.2031 (14) Å | Cell parameters from 2339 reflections |
b = 7.5946 (7) Å | θ = 2.7–25.0° |
c = 15.1270 (14) Å | µ = 0.10 mm−1 |
β = 100.143 (2)° | T = 292 K |
V = 1719.3 (3) Å3 | Block, colorless |
Z = 4 | 0.2 × 0.1 × 0.1 mm |
Bruker SMART CCD area detector diffractometer | 2559 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.026 |
Graphite monochromator | θmax = 26.0°, θmin = 2.7° |
ϕ and ω scans | h = −18→18 |
8803 measured reflections | k = −8→9 |
3379 independent reflections | l = −15→18 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0722P)2 + 0.1609P] where P = (Fo2 + 2Fc2)/3 |
3379 reflections | (Δ/σ)max < 0.001 |
226 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C18H18N2O5 | V = 1719.3 (3) Å3 |
Mr = 342.34 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.2031 (14) Å | µ = 0.10 mm−1 |
b = 7.5946 (7) Å | T = 292 K |
c = 15.1270 (14) Å | 0.2 × 0.1 × 0.1 mm |
β = 100.143 (2)° |
Bruker SMART CCD area detector diffractometer | 2559 reflections with I > 2σ(I) |
8803 measured reflections | Rint = 0.026 |
3379 independent reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.27 e Å−3 |
3379 reflections | Δρmin = −0.16 e Å−3 |
226 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.40899 (10) | 1.3222 (2) | 0.43955 (11) | 0.0430 (4) | |
C2 | 0.34531 (10) | 1.1906 (2) | 0.40264 (11) | 0.0412 (4) | |
C3 | 0.32290 (10) | 1.0534 (2) | 0.45385 (11) | 0.0405 (4) | |
C4 | 0.36887 (11) | 1.0329 (2) | 0.54334 (11) | 0.0456 (4) | |
C5 | 0.43235 (11) | 1.1546 (2) | 0.57887 (12) | 0.0464 (4) | |
C6 | 0.30640 (11) | 1.2085 (2) | 0.30983 (12) | 0.0441 (4) | |
C7 | 0.35129 (12) | 0.8795 (3) | 0.59942 (12) | 0.0541 (5) | |
C8 | 0.23996 (17) | 0.7002 (3) | 0.64431 (16) | 0.0776 (7) | |
H8A | 0.2571 | 0.7082 | 0.7091 | 0.093* | |
H8B | 0.2694 | 0.5987 | 0.6237 | 0.093* | |
C9 | 0.14130 (17) | 0.6825 (3) | 0.61880 (18) | 0.0881 (8) | |
H9A | 0.1221 | 0.5777 | 0.6454 | 0.132* | |
H9B | 0.1252 | 0.6751 | 0.5546 | 0.132* | |
H9C | 0.1129 | 0.7832 | 0.6399 | 0.132* | |
C10 | 0.48522 (13) | 1.1515 (3) | 0.67227 (13) | 0.0631 (5) | |
H10A | 0.5248 | 1.2509 | 0.6807 | 0.095* | |
H10B | 0.5195 | 1.0448 | 0.6812 | 0.095* | |
H10C | 0.4453 | 1.1569 | 0.7148 | 0.095* | |
C11 | 0.25205 (10) | 0.9258 (2) | 0.41475 (10) | 0.0405 (4) | |
C12 | 0.16453 (10) | 0.9831 (2) | 0.39121 (10) | 0.0384 (4) | |
C13 | 0.09645 (11) | 0.8634 (2) | 0.35838 (11) | 0.0444 (4) | |
C14 | 0.11747 (13) | 0.6886 (2) | 0.34890 (13) | 0.0551 (5) | |
H14A | 0.0727 | 0.6083 | 0.3269 | 0.066* | |
C15 | 0.20513 (14) | 0.6326 (3) | 0.37206 (14) | 0.0597 (5) | |
H15A | 0.2188 | 0.5145 | 0.3654 | 0.072* | |
C16 | 0.27223 (12) | 0.7487 (2) | 0.40471 (13) | 0.0524 (5) | |
H16A | 0.3309 | 0.7094 | 0.4201 | 0.063* | |
C17 | 0.11538 (15) | 1.1994 (3) | 0.48155 (16) | 0.0698 (6) | |
H17A | 0.1024 | 1.3230 | 0.4830 | 0.105* | |
H17B | 0.1618 | 1.1702 | 0.5311 | 0.105* | |
H17C | 0.0626 | 1.1330 | 0.4859 | 0.105* | |
C18 | −0.05858 (13) | 0.8161 (3) | 0.30424 (15) | 0.0657 (6) | |
H18A | −0.1137 | 0.8807 | 0.2921 | 0.099* | |
H18B | −0.0627 | 0.7266 | 0.3481 | 0.099* | |
H18C | −0.0475 | 0.7622 | 0.2498 | 0.099* | |
N1 | 0.44813 (9) | 1.29320 (19) | 0.52732 (10) | 0.0477 (4) | |
H1A | 0.4862 | 1.3702 | 0.5519 | 0.057* | |
N2 | 0.27760 (11) | 1.2211 (2) | 0.23497 (12) | 0.0656 (5) | |
O1 | 0.42765 (8) | 1.45469 (16) | 0.39909 (8) | 0.0525 (3) | |
O2 | 0.40881 (11) | 0.7845 (2) | 0.63687 (13) | 0.0896 (6) | |
O3 | 0.26547 (9) | 0.85995 (17) | 0.60199 (9) | 0.0570 (4) | |
O4 | 0.14408 (7) | 1.15804 (14) | 0.39973 (8) | 0.0461 (3) | |
O5 | 0.01266 (8) | 0.93290 (17) | 0.33772 (9) | 0.0571 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0337 (8) | 0.0416 (10) | 0.0515 (10) | 0.0016 (7) | 0.0009 (7) | −0.0033 (7) |
C2 | 0.0352 (8) | 0.0389 (9) | 0.0471 (9) | 0.0025 (7) | 0.0007 (7) | −0.0018 (7) |
C3 | 0.0353 (8) | 0.0369 (9) | 0.0475 (9) | 0.0036 (7) | 0.0023 (7) | −0.0021 (7) |
C4 | 0.0407 (8) | 0.0455 (10) | 0.0476 (9) | 0.0006 (8) | −0.0004 (7) | 0.0012 (7) |
C5 | 0.0371 (8) | 0.0499 (10) | 0.0497 (10) | 0.0023 (8) | 0.0005 (7) | −0.0015 (8) |
C6 | 0.0411 (9) | 0.0394 (9) | 0.0496 (10) | −0.0029 (7) | 0.0022 (7) | 0.0005 (7) |
C7 | 0.0530 (10) | 0.0551 (11) | 0.0489 (10) | −0.0004 (9) | −0.0057 (8) | 0.0055 (8) |
C8 | 0.0975 (18) | 0.0661 (14) | 0.0700 (14) | −0.0113 (13) | 0.0170 (12) | 0.0216 (11) |
C9 | 0.1015 (19) | 0.0786 (18) | 0.0890 (18) | −0.0343 (15) | 0.0305 (15) | 0.0021 (13) |
C10 | 0.0518 (11) | 0.0794 (15) | 0.0523 (11) | −0.0077 (10) | −0.0065 (9) | −0.0041 (10) |
C11 | 0.0442 (9) | 0.0362 (9) | 0.0390 (8) | −0.0020 (7) | 0.0016 (7) | −0.0003 (6) |
C12 | 0.0442 (9) | 0.0322 (8) | 0.0365 (8) | −0.0023 (7) | 0.0006 (7) | 0.0000 (6) |
C13 | 0.0448 (9) | 0.0448 (10) | 0.0410 (9) | −0.0053 (8) | 0.0005 (7) | −0.0010 (7) |
C14 | 0.0629 (12) | 0.0437 (11) | 0.0563 (11) | −0.0152 (9) | 0.0036 (9) | −0.0104 (8) |
C15 | 0.0705 (12) | 0.0350 (10) | 0.0718 (13) | 0.0013 (9) | 0.0080 (10) | −0.0099 (9) |
C16 | 0.0518 (10) | 0.0399 (10) | 0.0639 (12) | 0.0060 (8) | 0.0057 (9) | −0.0036 (8) |
C17 | 0.0818 (15) | 0.0545 (13) | 0.0757 (14) | 0.0071 (11) | 0.0214 (11) | −0.0120 (10) |
C18 | 0.0517 (11) | 0.0715 (15) | 0.0681 (13) | −0.0222 (10) | −0.0058 (9) | −0.0032 (10) |
N1 | 0.0385 (7) | 0.0473 (9) | 0.0532 (9) | −0.0067 (6) | −0.0029 (6) | −0.0051 (7) |
N2 | 0.0654 (10) | 0.0727 (12) | 0.0546 (10) | −0.0046 (9) | −0.0010 (8) | 0.0033 (8) |
O1 | 0.0480 (7) | 0.0434 (7) | 0.0619 (8) | −0.0079 (6) | −0.0017 (6) | 0.0047 (6) |
O2 | 0.0730 (10) | 0.0874 (12) | 0.0991 (12) | 0.0109 (9) | −0.0103 (9) | 0.0411 (10) |
O3 | 0.0605 (8) | 0.0515 (8) | 0.0581 (8) | −0.0057 (6) | 0.0082 (6) | 0.0114 (6) |
O4 | 0.0456 (6) | 0.0347 (7) | 0.0553 (7) | 0.0011 (5) | 0.0016 (5) | 0.0005 (5) |
O5 | 0.0409 (6) | 0.0525 (8) | 0.0718 (9) | −0.0097 (6) | −0.0072 (6) | −0.0029 (6) |
C1—O1 | 1.236 (2) | C10—H10B | 0.9600 |
C1—N1 | 1.374 (2) | C10—H10C | 0.9600 |
C1—C2 | 1.435 (2) | C11—C12 | 1.385 (2) |
C2—C3 | 1.376 (2) | C11—C16 | 1.394 (2) |
C2—C6 | 1.431 (2) | C12—O4 | 1.3761 (19) |
C3—C4 | 1.419 (2) | C12—C13 | 1.401 (2) |
C3—C11 | 1.492 (2) | C13—O5 | 1.363 (2) |
C4—C5 | 1.376 (2) | C13—C14 | 1.379 (3) |
C4—C7 | 1.493 (3) | C14—C15 | 1.384 (3) |
C5—N1 | 1.356 (2) | C14—H14A | 0.9300 |
C5—C10 | 1.497 (2) | C15—C16 | 1.373 (3) |
C6—N2 | 1.144 (2) | C15—H15A | 0.9300 |
C7—O2 | 1.196 (2) | C16—H16A | 0.9300 |
C7—O3 | 1.321 (2) | C17—O4 | 1.418 (2) |
C8—O3 | 1.456 (2) | C17—H17A | 0.9600 |
C8—C9 | 1.488 (3) | C17—H17B | 0.9600 |
C8—H8A | 0.9700 | C17—H17C | 0.9600 |
C8—H8B | 0.9700 | C18—O5 | 1.422 (2) |
C9—H9A | 0.9600 | C18—H18A | 0.9600 |
C9—H9B | 0.9600 | C18—H18B | 0.9600 |
C9—H9C | 0.9600 | C18—H18C | 0.9600 |
C10—H10A | 0.9600 | N1—H1A | 0.8600 |
O1—C1—N1 | 120.73 (14) | C12—C11—C16 | 119.65 (15) |
O1—C1—C2 | 124.92 (15) | C12—C11—C3 | 119.47 (14) |
N1—C1—C2 | 114.33 (15) | C16—C11—C3 | 120.84 (15) |
C3—C2—C6 | 121.57 (14) | O4—C12—C11 | 120.10 (13) |
C3—C2—C1 | 121.70 (15) | O4—C12—C13 | 119.65 (14) |
C6—C2—C1 | 116.73 (15) | C11—C12—C13 | 120.25 (15) |
C2—C3—C4 | 119.42 (14) | O5—C13—C14 | 124.99 (15) |
C2—C3—C11 | 120.11 (14) | O5—C13—C12 | 115.60 (15) |
C4—C3—C11 | 120.46 (14) | C14—C13—C12 | 119.41 (16) |
C5—C4—C3 | 119.53 (16) | C13—C14—C15 | 120.02 (17) |
C5—C4—C7 | 119.07 (15) | C13—C14—H14A | 120.0 |
C3—C4—C7 | 121.39 (15) | C15—C14—H14A | 120.0 |
N1—C5—C4 | 118.67 (15) | C16—C15—C14 | 121.00 (18) |
N1—C5—C10 | 115.76 (15) | C16—C15—H15A | 119.5 |
C4—C5—C10 | 125.54 (16) | C14—C15—H15A | 119.5 |
N2—C6—C2 | 178.00 (18) | C15—C16—C11 | 119.68 (17) |
O2—C7—O3 | 124.17 (19) | C15—C16—H16A | 120.2 |
O2—C7—C4 | 123.41 (18) | C11—C16—H16A | 120.2 |
O3—C7—C4 | 112.41 (15) | O4—C17—H17A | 109.5 |
O3—C8—C9 | 107.19 (19) | O4—C17—H17B | 109.5 |
O3—C8—H8A | 110.3 | H17A—C17—H17B | 109.5 |
C9—C8—H8A | 110.3 | O4—C17—H17C | 109.5 |
O3—C8—H8B | 110.3 | H17A—C17—H17C | 109.5 |
C9—C8—H8B | 110.3 | H17B—C17—H17C | 109.5 |
H8A—C8—H8B | 108.5 | O5—C18—H18A | 109.5 |
C8—C9—H9A | 109.5 | O5—C18—H18B | 109.5 |
C8—C9—H9B | 109.5 | H18A—C18—H18B | 109.5 |
H9A—C9—H9B | 109.5 | O5—C18—H18C | 109.5 |
C8—C9—H9C | 109.5 | H18A—C18—H18C | 109.5 |
H9A—C9—H9C | 109.5 | H18B—C18—H18C | 109.5 |
H9B—C9—H9C | 109.5 | C5—N1—C1 | 126.15 (14) |
C5—C10—H10A | 109.5 | C5—N1—H1A | 116.9 |
C5—C10—H10B | 109.5 | C1—N1—H1A | 116.9 |
H10A—C10—H10B | 109.5 | C7—O3—C8 | 116.59 (16) |
C5—C10—H10C | 109.5 | C12—O4—C17 | 113.89 (14) |
H10A—C10—H10C | 109.5 | C13—O5—C18 | 117.53 (14) |
H10B—C10—H10C | 109.5 | ||
O1—C1—C2—C3 | −174.95 (16) | C3—C11—C12—O4 | 3.2 (2) |
N1—C1—C2—C3 | 3.4 (2) | C16—C11—C12—C13 | 0.7 (2) |
O1—C1—C2—C6 | 5.2 (2) | C3—C11—C12—C13 | −176.97 (14) |
N1—C1—C2—C6 | −176.37 (14) | O4—C12—C13—O5 | −0.6 (2) |
C6—C2—C3—C4 | 174.61 (15) | C11—C12—C13—O5 | 179.60 (14) |
C1—C2—C3—C4 | −5.2 (2) | O4—C12—C13—C14 | 179.18 (15) |
C6—C2—C3—C11 | −4.2 (2) | C11—C12—C13—C14 | −0.6 (2) |
C1—C2—C3—C11 | 175.96 (14) | O5—C13—C14—C15 | 179.99 (17) |
C2—C3—C4—C5 | 2.8 (2) | C12—C13—C14—C15 | 0.2 (3) |
C11—C3—C4—C5 | −178.31 (15) | C13—C14—C15—C16 | 0.1 (3) |
C2—C3—C4—C7 | −175.82 (16) | C14—C15—C16—C11 | 0.0 (3) |
C11—C3—C4—C7 | 3.0 (2) | C12—C11—C16—C15 | −0.3 (3) |
C3—C4—C5—N1 | 1.1 (2) | C3—C11—C16—C15 | 177.27 (17) |
C7—C4—C5—N1 | 179.75 (16) | C4—C5—N1—C1 | −2.9 (3) |
C3—C4—C5—C10 | 179.17 (16) | C10—C5—N1—C1 | 178.79 (16) |
C7—C4—C5—C10 | −2.1 (3) | O1—C1—N1—C5 | 179.16 (16) |
C5—C4—C7—O2 | −51.8 (3) | C2—C1—N1—C5 | 0.7 (2) |
C3—C4—C7—O2 | 126.9 (2) | O2—C7—O3—C8 | −7.7 (3) |
C5—C4—C7—O3 | 128.92 (17) | C4—C7—O3—C8 | 171.60 (17) |
C3—C4—C7—O3 | −52.4 (2) | C9—C8—O3—C7 | −165.37 (19) |
C2—C3—C11—C12 | −65.9 (2) | C11—C12—O4—C17 | −95.16 (18) |
C4—C3—C11—C12 | 115.23 (17) | C13—C12—O4—C17 | 85.03 (19) |
C2—C3—C11—C16 | 116.45 (18) | C14—C13—O5—C18 | 0.3 (3) |
C4—C3—C11—C16 | −62.4 (2) | C12—C13—O5—C18 | −179.93 (15) |
C16—C11—C12—O4 | −179.13 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16A···O1i | 0.93 | 2.48 | 3.263 (1) | 141 |
N1—H1A···O1ii | 0.86 | 1.92 | 2.780 (2) | 177 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+3, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C18H18N2O5 |
Mr | 342.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 292 |
a, b, c (Å) | 15.2031 (14), 7.5946 (7), 15.1270 (14) |
β (°) | 100.143 (2) |
V (Å3) | 1719.3 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.2 × 0.1 × 0.1 |
Data collection | |
Diffractometer | Bruker SMART CCD area detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8803, 3379, 2559 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.137, 1.07 |
No. of reflections | 3379 |
No. of parameters | 226 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.16 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.
C1—N1 | 1.374 (2) | C3—C4 | 1.419 (2) |
C1—C2 | 1.435 (2) | C4—C5 | 1.376 (2) |
C2—C3 | 1.376 (2) | C5—N1 | 1.356 (2) |
N1—C1—C2 | 114.33 (15) | C5—C4—C3 | 119.53 (16) |
C3—C2—C1 | 121.70 (15) | N1—C5—C4 | 118.67 (15) |
C2—C3—C4 | 119.42 (14) | C5—N1—C1 | 126.15 (14) |
N1—C1—C2—C3 | 3.4 (2) | C3—C4—C7—O3 | −52.4 (2) |
C1—C2—C3—C4 | −5.2 (2) | C2—C3—C11—C12 | −65.9 (2) |
C2—C3—C4—C5 | 2.8 (2) | C4—C5—N1—C1 | −2.9 (3) |
C3—C4—C5—N1 | 1.1 (2) | C2—C1—N1—C5 | 0.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16A···O1i | 0.93 | 2.48 | 3.263 (1) | 141 |
N1—H1A···O1ii | 0.86 | 1.92 | 2.780 (2) | 177 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+3, −z+1. |
It is known that many pyridine derivatives exhibit a wide spectrum of pharmacological activities and biological activities, such as inhibitory activity (Liu et al., 1980 or 2002?), antimicrobial activity (Aytemir et al., 2003) and anti-inflammatory activity (Ozturk et al., 2002). We report here the crystal structure of the title compound, (I). Its aqueous synthesis (see Experimental) was inspired by the work of Breslow & Rideout (1980), who rediscovered the use of water as a solvent in organic chemistry.
In (I), the C2—C3 bond distance of 1.376 (2) Å is equal to the value of 1.376 (2) Å for C4—C5, indicating double-bond character in both cases, which indicates that the further aromatization took place unexpectedly. The pyridine ring (C1—C5/N1) are essentially planar (Fig. 1), with a maximum deviation of 0.026 (1) Å for C2. This ring forms a dihedral angle of 63.8 (1)° with the benzene ring (C11–C16). Molecules form centrosymmetric dimers by N1—H1A···O1 (1 − x, 3 − y, 1 − z) hydrogen bonds (Table 2), and they are further linked via C16—H16A···O1 (x, y − 1, z) interactions (Fig. 2).