Phenyl 2-picolinamido­benzoate

In the title compound, C₁₉H₁₄N₂O₃, all bond lengths and angles show normal values. The mol­ecules are linked by C—H...O hydrogen bonds, forming dimers which are arranged parallel to the a axis.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](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

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Computing details

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

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.100	H-atom parameters constrained
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0404P)^2] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O3^i	0.93	2.54	3.269 (2)	133

Symmetry code: (i) −x+3, −y+2, −z+1.