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organic compounds
In the title compound, C19H14N2O3, all bond lengths and angles show normal values. The molecules are linked by C—HO hydrogen bonds, forming dimers which are arranged parallel to the a axis.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806016382/ym2001sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806016382/ym2001Isup2.hkl |
CCDC reference: 610943
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.003 Å
- R factor = 0.048
- wR factor = 0.100
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C7 - C8 .. 5.30 su PLAT728_ALERT_1_C D-H..A Calc 135.00, Rep 133.00 Dev... 2.00 Deg. C19 -H19A -O3 1.555 1.555 2.876
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
Phenyl 2-nicotinamidobenzoate top
Crystal data top
C19H14N2O3 | Z = 2 |
Mr = 318.32 | F(000) = 332 |
Triclinic, P1 | Dx = 1.393 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.657 (2) Å | Cell parameters from 1525 reflections |
b = 11.700 (4) Å | θ = 1.7–26.0° |
c = 11.793 (4) Å | µ = 0.10 mm−1 |
α = 98.910 (8)° | T = 292 K |
β = 97.291 (9)° | Block, colourless |
γ = 96.008 (7)° | 0.30 × 0.20 × 0.10 mm |
V = 758.7 (5) Å3 |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2965 independent reflections |
Radiation source: fine-focus sealed tube | 1895 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.059 |
Detector resolution: 83.66 pixels mm-1 | θmax = 26.0°, θmin = 1.7° |
ω scans | h = −6→6 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −14→14 |
Tmin = 0.971, Tmax = 0.990 | l = −14→14 |
8013 measured reflections |
Refinement top
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H-atom parameters constrained |
S = 0.91 | w = 1/[σ2(Fo2) + (0.0404P)2] where P = (Fo2 + 2Fc2)/3 |
2965 reflections | (Δ/σ)max < 0.001 |
217 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O2 | 0.5737 (2) | 0.77499 (11) | 0.08049 (10) | 0.0550 (4) | |
O1 | 0.2550 (2) | 0.64053 (11) | 0.06645 (10) | 0.0562 (4) | |
O3 | 1.1388 (2) | 0.89121 (12) | 0.45048 (11) | 0.0658 (4) | |
N1 | 0.8591 (2) | 0.83152 (12) | 0.28852 (11) | 0.0445 (4) | |
H1B | 0.8314 | 0.8381 | 0.2166 | 0.053* | |
N2 | 1.1266 (3) | 0.95815 (13) | 0.16759 (12) | 0.0491 (4) | |
C1 | 0.0137 (3) | 0.69998 (17) | −0.08912 (16) | 0.0552 (5) | |
H1A | −0.0710 | 0.7388 | −0.0358 | 0.066* | |
C2 | −0.0474 (3) | 0.69855 (17) | −0.20690 (17) | 0.0576 (5) | |
H2A | −0.1731 | 0.7376 | −0.2330 | 0.069* | |
C3 | 0.0760 (3) | 0.64012 (16) | −0.28502 (16) | 0.0518 (5) | |
H3A | 0.0333 | 0.6390 | −0.3640 | 0.062* | |
C4 | 0.2623 (4) | 0.58332 (16) | −0.24673 (16) | 0.0552 (5) | |
H4A | 0.3458 | 0.5436 | −0.3000 | 0.066* | |
C5 | 0.3269 (3) | 0.58463 (15) | −0.12995 (16) | 0.0525 (5) | |
H5A | 0.4538 | 0.5464 | −0.1037 | 0.063* | |
C6 | 0.2004 (3) | 0.64334 (15) | −0.05317 (15) | 0.0445 (4) | |
C7 | 0.4492 (3) | 0.71242 (15) | 0.12722 (14) | 0.0410 (4) | |
C8 | 0.4817 (3) | 0.70152 (14) | 0.25079 (14) | 0.0386 (4) | |
C9 | 0.3088 (3) | 0.63207 (15) | 0.29266 (15) | 0.0471 (5) | |
H9A | 0.1756 | 0.5930 | 0.2418 | 0.056* | |
C10 | 0.3304 (4) | 0.62008 (16) | 0.40706 (15) | 0.0554 (5) | |
H10A | 0.2133 | 0.5735 | 0.4337 | 0.066* | |
C11 | 0.5280 (4) | 0.67786 (17) | 0.48205 (16) | 0.0603 (6) | |
H11A | 0.5434 | 0.6701 | 0.5599 | 0.072* | |
C12 | 0.7026 (3) | 0.74675 (16) | 0.44408 (15) | 0.0549 (5) | |
H12A | 0.8349 | 0.7846 | 0.4963 | 0.066* | |
C13 | 0.6839 (3) | 0.76068 (14) | 0.32821 (14) | 0.0406 (4) | |
C14 | 1.0681 (3) | 0.89158 (15) | 0.34899 (15) | 0.0440 (4) | |
C15 | 1.2137 (3) | 0.96070 (14) | 0.27886 (14) | 0.0418 (4) | |
C16 | 1.2623 (3) | 1.02017 (17) | 0.10772 (16) | 0.0560 (5) | |
H16A | 1.2050 | 1.0204 | 0.0303 | 0.067* | |
C17 | 1.4809 (3) | 1.08338 (16) | 0.15369 (16) | 0.0557 (5) | |
H17A | 1.5678 | 1.1255 | 0.1085 | 0.067* | |
C18 | 1.5680 (3) | 1.08327 (16) | 0.26667 (17) | 0.0572 (5) | |
H18A | 1.7166 | 1.1244 | 0.2999 | 0.069* | |
C19 | 1.4315 (3) | 1.02104 (16) | 0.33077 (16) | 0.0529 (5) | |
H19A | 1.4863 | 1.0199 | 0.4083 | 0.063* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0554 (8) | 0.0648 (9) | 0.0412 (7) | −0.0138 (7) | 0.0027 (6) | 0.0164 (6) |
O1 | 0.0568 (8) | 0.0664 (9) | 0.0394 (7) | −0.0184 (7) | −0.0006 (6) | 0.0139 (6) |
O3 | 0.0617 (9) | 0.0856 (10) | 0.0436 (8) | −0.0148 (7) | −0.0078 (6) | 0.0194 (7) |
N1 | 0.0422 (9) | 0.0540 (9) | 0.0359 (8) | −0.0018 (7) | 0.0020 (7) | 0.0120 (7) |
N2 | 0.0451 (9) | 0.0590 (10) | 0.0416 (9) | 0.0004 (7) | 0.0033 (7) | 0.0107 (7) |
C1 | 0.0475 (12) | 0.0680 (13) | 0.0478 (12) | 0.0049 (10) | 0.0089 (9) | 0.0025 (10) |
C2 | 0.0470 (12) | 0.0669 (13) | 0.0555 (13) | 0.0078 (10) | −0.0033 (10) | 0.0087 (10) |
C3 | 0.0567 (12) | 0.0542 (12) | 0.0400 (11) | −0.0051 (10) | 0.0008 (9) | 0.0078 (9) |
C4 | 0.0616 (13) | 0.0560 (12) | 0.0494 (12) | 0.0079 (10) | 0.0161 (10) | 0.0060 (9) |
C5 | 0.0534 (12) | 0.0534 (12) | 0.0520 (12) | 0.0089 (10) | 0.0047 (10) | 0.0143 (9) |
C6 | 0.0447 (11) | 0.0492 (11) | 0.0358 (10) | −0.0104 (9) | 0.0015 (8) | 0.0099 (8) |
C7 | 0.0395 (10) | 0.0411 (10) | 0.0418 (10) | 0.0026 (8) | 0.0064 (8) | 0.0071 (8) |
C8 | 0.0428 (10) | 0.0387 (10) | 0.0355 (9) | 0.0059 (8) | 0.0072 (8) | 0.0087 (8) |
C9 | 0.0486 (11) | 0.0481 (11) | 0.0432 (11) | −0.0035 (9) | 0.0092 (9) | 0.0078 (8) |
C10 | 0.0608 (13) | 0.0594 (12) | 0.0466 (12) | −0.0068 (10) | 0.0157 (10) | 0.0141 (10) |
C11 | 0.0699 (14) | 0.0723 (14) | 0.0387 (11) | −0.0042 (11) | 0.0102 (10) | 0.0164 (10) |
C12 | 0.0548 (12) | 0.0662 (13) | 0.0408 (11) | −0.0043 (10) | 0.0015 (9) | 0.0133 (9) |
C13 | 0.0441 (11) | 0.0417 (10) | 0.0376 (10) | 0.0044 (8) | 0.0083 (8) | 0.0104 (8) |
C14 | 0.0437 (11) | 0.0458 (11) | 0.0401 (11) | 0.0030 (8) | 0.0002 (8) | 0.0070 (8) |
C15 | 0.0408 (10) | 0.0415 (10) | 0.0416 (10) | 0.0047 (8) | 0.0018 (8) | 0.0069 (8) |
C16 | 0.0518 (12) | 0.0709 (14) | 0.0461 (11) | 0.0006 (11) | 0.0060 (9) | 0.0180 (10) |
C17 | 0.0512 (12) | 0.0570 (12) | 0.0613 (13) | −0.0005 (10) | 0.0115 (10) | 0.0198 (10) |
C18 | 0.0484 (12) | 0.0547 (12) | 0.0634 (13) | −0.0098 (9) | −0.0029 (10) | 0.0147 (10) |
C19 | 0.0521 (12) | 0.0540 (12) | 0.0479 (11) | −0.0053 (9) | −0.0048 (9) | 0.0121 (9) |
Geometric parameters (Å, º) top
O2—C7 | 1.2046 (18) | C7—C8 | 1.472 (2) |
O1—C7 | 1.3593 (19) | C8—C9 | 1.393 (2) |
O1—C6 | 1.412 (2) | C8—C13 | 1.412 (2) |
O3—C14 | 1.2137 (19) | C9—C10 | 1.369 (2) |
N1—C14 | 1.363 (2) | C9—H9A | 0.9300 |
N1—C13 | 1.398 (2) | C10—C11 | 1.376 (3) |
N1—H1B | 0.8600 | C10—H10A | 0.9300 |
N2—C15 | 1.337 (2) | C11—C12 | 1.372 (3) |
N2—C16 | 1.340 (2) | C11—H11A | 0.9300 |
C1—C6 | 1.362 (2) | C12—C13 | 1.393 (2) |
C1—C2 | 1.385 (2) | C12—H12A | 0.9300 |
C1—H1A | 0.9300 | C14—C15 | 1.503 (2) |
C2—C3 | 1.368 (2) | C15—C19 | 1.372 (2) |
C2—H2A | 0.9300 | C16—C17 | 1.373 (3) |
C3—C4 | 1.370 (2) | C16—H16A | 0.9300 |
C3—H3A | 0.9300 | C17—C18 | 1.361 (2) |
C4—C5 | 1.377 (2) | C17—H17A | 0.9300 |
C4—H4A | 0.9300 | C18—C19 | 1.378 (2) |
C5—C6 | 1.370 (2) | C18—H18A | 0.9300 |
C5—H5A | 0.9300 | C19—H19A | 0.9300 |
C7—O1—C6 | 117.79 (13) | C8—C9—H9A | 119.3 |
C14—N1—C13 | 128.46 (14) | C9—C10—C11 | 119.07 (17) |
C14—N1—H1B | 115.8 | C9—C10—H10A | 120.5 |
C13—N1—H1B | 115.8 | C11—C10—H10A | 120.5 |
C15—N2—C16 | 116.32 (16) | C12—C11—C10 | 121.18 (17) |
C6—C1—C2 | 118.54 (18) | C12—C11—H11A | 119.4 |
C6—C1—H1A | 120.7 | C10—C11—H11A | 119.4 |
C2—C1—H1A | 120.7 | C11—C12—C13 | 120.78 (18) |
C3—C2—C1 | 120.43 (19) | C11—C12—H12A | 119.6 |
C3—C2—H2A | 119.8 | C13—C12—H12A | 119.6 |
C1—C2—H2A | 119.8 | C12—C13—N1 | 121.42 (16) |
C2—C3—C4 | 119.91 (18) | C12—C13—C8 | 118.32 (16) |
C2—C3—H3A | 120.0 | N1—C13—C8 | 120.27 (15) |
C4—C3—H3A | 120.0 | O3—C14—N1 | 125.03 (17) |
C3—C4—C5 | 120.47 (18) | O3—C14—C15 | 120.68 (16) |
C3—C4—H4A | 119.8 | N1—C14—C15 | 114.29 (15) |
C5—C4—H4A | 119.8 | N2—C15—C19 | 123.10 (16) |
C6—C5—C4 | 118.68 (18) | N2—C15—C14 | 118.07 (15) |
C6—C5—H5A | 120.7 | C19—C15—C14 | 118.81 (16) |
C4—C5—H5A | 120.7 | N2—C16—C17 | 124.00 (18) |
C1—C6—C5 | 121.96 (17) | N2—C16—H16A | 118.0 |
C1—C6—O1 | 118.34 (16) | C17—C16—H16A | 118.0 |
C5—C6—O1 | 119.62 (17) | C18—C17—C16 | 118.70 (18) |
O2—C7—O1 | 121.33 (15) | C18—C17—H17A | 120.7 |
O2—C7—C8 | 126.91 (16) | C16—C17—H17A | 120.7 |
O1—C7—C8 | 111.76 (14) | C17—C18—C19 | 118.64 (18) |
C9—C8—C13 | 119.16 (15) | C17—C18—H18A | 120.7 |
C9—C8—C7 | 119.44 (16) | C19—C18—H18A | 120.7 |
C13—C8—C7 | 121.40 (15) | C15—C19—C18 | 119.24 (18) |
C10—C9—C8 | 121.49 (17) | C15—C19—H19A | 120.4 |
C10—C9—H9A | 119.3 | C18—C19—H19A | 120.4 |
C6—C1—C2—C3 | 0.8 (3) | C11—C12—C13—C8 | −0.4 (3) |
C1—C2—C3—C4 | −0.5 (3) | C14—N1—C13—C12 | 2.7 (3) |
C2—C3—C4—C5 | −0.1 (3) | C14—N1—C13—C8 | −177.59 (16) |
C3—C4—C5—C6 | 0.3 (3) | C9—C8—C13—C12 | 0.2 (2) |
C2—C1—C6—C5 | −0.6 (3) | C7—C8—C13—C12 | 179.74 (15) |
C2—C1—C6—O1 | −177.17 (16) | C9—C8—C13—N1 | −179.56 (15) |
C4—C5—C6—C1 | 0.1 (3) | C7—C8—C13—N1 | 0.0 (2) |
C4—C5—C6—O1 | 176.58 (15) | C13—N1—C14—O3 | 1.3 (3) |
C7—O1—C6—C1 | −103.79 (19) | C13—N1—C14—C15 | −179.28 (14) |
C7—O1—C6—C5 | 79.6 (2) | C16—N2—C15—C19 | −1.1 (3) |
C6—O1—C7—O2 | −1.4 (2) | C16—N2—C15—C14 | −179.53 (15) |
C6—O1—C7—C8 | 179.06 (14) | O3—C14—C15—N2 | −179.80 (16) |
O2—C7—C8—C9 | 174.51 (17) | N1—C14—C15—N2 | 0.7 (2) |
O1—C7—C8—C9 | −6.0 (2) | O3—C14—C15—C19 | 1.7 (3) |
O2—C7—C8—C13 | −5.0 (3) | N1—C14—C15—C19 | −177.75 (15) |
O1—C7—C8—C13 | 174.50 (15) | C15—N2—C16—C17 | 0.6 (3) |
C13—C8—C9—C10 | 0.1 (3) | N2—C16—C17—C18 | 0.4 (3) |
C7—C8—C9—C10 | −179.47 (16) | C16—C17—C18—C19 | −0.9 (3) |
C8—C9—C10—C11 | −0.1 (3) | N2—C15—C19—C18 | 0.6 (3) |
C9—C10—C11—C12 | −0.1 (3) | C14—C15—C19—C18 | 179.05 (16) |
C10—C11—C12—C13 | 0.4 (3) | C17—C18—C19—C15 | 0.4 (3) |
C11—C12—C13—N1 | 179.33 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O2 | 0.86 | 2.02 | 2.708 (2) | 137 |
N1—H1B···N2 | 0.86 | 2.26 | 2.693 (2) | 111 |
C9—H9A···O1 | 0.93 | 2.31 | 2.665 (2) | 102 |
C12—H12A···O3 | 0.93 | 2.19 | 2.827 (2) | 125 |
C19—H19A···O3i | 0.93 | 2.54 | 3.269 (2) | 133 |
Symmetry code: (i) −x+3, −y+2, −z+1. |
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