Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036318/ci2426sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036318/ci2426Isup2.hkl |
CCDC reference: 657853
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.003 Å
- R factor = 0.041
- wR factor = 0.108
- Data-to-parameter ratio = 8.5
checkCIF/PLATON results
No syntax errors found
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.47 From the CIF: _reflns_number_total 1494 Count of symmetry unique reflns 1497 Completeness (_total/calc) 99.80% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For general background, see: Matarrese et al. (2001); Perlepes et al. (1986). For synthesis, see: Davis (1959).
The title compound was synthesized from 2-quinolinecarboxylic acid and aniline according to the general procedure of Davis (1959). Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from dimethylsulfoxide.
The N-bound H atom was located in a difference Fourier map and refined isotropically [N—H = 0.93 (3) Å]. C-bound H atoms were placed in calculated positions, with C—H = 0.95 Å, and refined using a riding model, with Uiso(H) = 1.2Ueq(C). In the absence of significant anomalous dispersion effects, Friedel pairs were merged before the final refinement.
Quinoline-2-carboxamide compounds are a class of important materials as metal ligands (Perlepes et al., 1986) and as potential radioligands for visualization of peripheral benzodiazepine receptors (Matarrese et al., 2001). We report here the crystal structure of the title compound, (I).
The O1—C11 [1.223 (3) Å], N2—C11 [1.365 (3) Å] and N2—C12 [1.412 (3) Å] bond lengths indicate extensive electron delocalization in the amide linkage. The quinoline ring system is planar within ±0.013 (2) Å. The dihedral angle between the C2/C3/C4/C9/C10/N1 and C2/C11/O1/N2 planes is 4.6 (1)° and that between C2/C11/O1/N2 and C12—C17 planes is 2.5 (1)° (Fig 1). The dihedral angle between the quinoline ring system and phenyl ring is 6.8 (1)°. Weak N—H···N and C—H···O hydrogen bonds are observed in the molecular structure (Table 1).
For general background, see: Matarrese et al. (2001); Perlepes et al. (1986). For synthesis, see: Davis (1959).
Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL97.
Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atomic numbering. |
C16H12N2O | F(000) = 520 |
Mr = 248.28 | Dx = 1.390 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 8549 reflections |
a = 16.9856 (19) Å | θ = 3.2–27.5° |
b = 12.8279 (16) Å | µ = 0.09 mm−1 |
c = 5.4455 (7) Å | T = 153 K |
V = 1186.5 (3) Å3 | Plate, colourless |
Z = 4 | 0.52 × 0.30 × 0.09 mm |
Rigaku R-AXIS RAPID diffractometer | 1306 reflections with I > 2σ(I) |
Radiation source: Rotating Anode | Rint = 0.069 |
Graphite monochromator | θmax = 27.5°, θmin = 3.2° |
ω scans | h = −21→22 |
11138 measured reflections | k = −16→16 |
1494 independent reflections | l = −7→7 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0686P)2] where P = (Fo2 + 2Fc2)/3 |
1494 reflections | (Δ/σ)max = 0.001 |
176 parameters | Δρmax = 0.15 e Å−3 |
1 restraint | Δρmin = −0.20 e Å−3 |
C16H12N2O | V = 1186.5 (3) Å3 |
Mr = 248.28 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 16.9856 (19) Å | µ = 0.09 mm−1 |
b = 12.8279 (16) Å | T = 153 K |
c = 5.4455 (7) Å | 0.52 × 0.30 × 0.09 mm |
Rigaku R-AXIS RAPID diffractometer | 1306 reflections with I > 2σ(I) |
11138 measured reflections | Rint = 0.069 |
1494 independent reflections |
R[F2 > 2σ(F2)] = 0.041 | 1 restraint |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.15 e Å−3 |
1494 reflections | Δρmin = −0.20 e Å−3 |
176 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 | ||
O1 | 0.28453 (9) | 0.31035 (13) | 0.1870 (3) | 0.0383 (4) | |
N1 | 0.37707 (10) | 0.43801 (13) | 0.6855 (4) | 0.0289 (4) | |
N2 | 0.41118 (10) | 0.29930 (14) | 0.3349 (4) | 0.0318 (4) | |
C2 | 0.31803 (12) | 0.40935 (16) | 0.5420 (4) | 0.0300 (5) | |
C3 | 0.24023 (13) | 0.44684 (16) | 0.5661 (5) | 0.0346 (5) | |
H3 | 0.1996 | 0.4227 | 0.4606 | 0.042* | |
C4 | 0.22498 (13) | 0.51849 (17) | 0.7444 (5) | 0.0338 (5) | |
H4 | 0.1732 | 0.5453 | 0.7639 | 0.041* | |
C5 | 0.27477 (13) | 0.62705 (17) | 1.0899 (5) | 0.0340 (5) | |
H5 | 0.2241 | 0.6566 | 1.1136 | 0.041* | |
C6 | 0.33486 (13) | 0.65688 (16) | 1.2390 (5) | 0.0345 (5) | |
H6 | 0.3261 | 0.7070 | 1.3645 | 0.041* | |
C7 | 0.41086 (13) | 0.61262 (15) | 1.2059 (5) | 0.0333 (5) | |
H7 | 0.4530 | 0.6330 | 1.3101 | 0.040* | |
C8 | 0.42357 (12) | 0.54080 (16) | 1.0248 (5) | 0.0314 (5) | |
H8 | 0.4747 | 0.5118 | 1.0052 | 0.038* | |
C9 | 0.36231 (11) | 0.50866 (16) | 0.8660 (4) | 0.0276 (4) | |
C10 | 0.28592 (12) | 0.55297 (16) | 0.9001 (4) | 0.0303 (5) | |
C11 | 0.33541 (12) | 0.33470 (16) | 0.3353 (4) | 0.0296 (5) | |
C12 | 0.44804 (12) | 0.23178 (15) | 0.1655 (4) | 0.0307 (5) | |
C13 | 0.52679 (12) | 0.20587 (15) | 0.2071 (5) | 0.0331 (5) | |
H13 | 0.5536 | 0.2332 | 0.3459 | 0.040* | |
C14 | 0.56576 (13) | 0.14009 (17) | 0.0450 (5) | 0.0347 (5) | |
H14 | 0.6196 | 0.1235 | 0.0722 | 0.042* | |
C15 | 0.52686 (13) | 0.09850 (17) | −0.1561 (5) | 0.0364 (5) | |
H15 | 0.5534 | 0.0527 | −0.2652 | 0.044* | |
C16 | 0.44909 (15) | 0.12453 (16) | −0.1958 (5) | 0.0368 (5) | |
H16 | 0.4224 | 0.0965 | −0.3341 | 0.044* | |
C17 | 0.40915 (13) | 0.19058 (17) | −0.0381 (4) | 0.0339 (5) | |
H17 | 0.3556 | 0.2078 | −0.0684 | 0.041* | |
H2N | 0.4423 (14) | 0.3254 (19) | 0.462 (6) | 0.043 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0378 (8) | 0.0424 (9) | 0.0347 (9) | −0.0023 (7) | −0.0050 (8) | −0.0061 (8) |
N1 | 0.0326 (9) | 0.0263 (8) | 0.0280 (9) | −0.0012 (7) | 0.0010 (8) | 0.0025 (8) |
N2 | 0.0349 (9) | 0.0329 (10) | 0.0275 (10) | −0.0001 (8) | −0.0023 (8) | −0.0049 (9) |
C2 | 0.0327 (10) | 0.0291 (9) | 0.0283 (11) | −0.0021 (9) | 0.0002 (9) | 0.0023 (9) |
C3 | 0.0330 (10) | 0.0372 (12) | 0.0337 (12) | −0.0027 (9) | −0.0046 (10) | 0.0033 (10) |
C4 | 0.0306 (10) | 0.0364 (11) | 0.0343 (12) | 0.0036 (9) | 0.0020 (9) | 0.0049 (11) |
C5 | 0.0358 (11) | 0.0335 (11) | 0.0329 (12) | 0.0041 (9) | 0.0045 (10) | 0.0025 (10) |
C6 | 0.0438 (12) | 0.0273 (10) | 0.0323 (12) | 0.0010 (9) | 0.0061 (10) | −0.0001 (10) |
C7 | 0.0392 (12) | 0.0312 (10) | 0.0295 (12) | −0.0038 (9) | −0.0011 (9) | −0.0001 (10) |
C8 | 0.0323 (11) | 0.0304 (10) | 0.0316 (12) | −0.0012 (9) | 0.0012 (9) | 0.0029 (10) |
C9 | 0.0321 (10) | 0.0254 (9) | 0.0253 (10) | −0.0008 (8) | 0.0042 (9) | 0.0055 (9) |
C10 | 0.0355 (11) | 0.0262 (10) | 0.0292 (11) | 0.0003 (8) | 0.0058 (9) | 0.0036 (9) |
C11 | 0.0343 (11) | 0.0273 (11) | 0.0271 (11) | −0.0026 (8) | 0.0020 (9) | 0.0030 (9) |
C12 | 0.0399 (11) | 0.0238 (10) | 0.0285 (11) | 0.0000 (9) | 0.0005 (10) | 0.0015 (9) |
C13 | 0.0414 (12) | 0.0299 (10) | 0.0282 (12) | −0.0017 (9) | −0.0033 (10) | 0.0015 (10) |
C14 | 0.0373 (11) | 0.0343 (11) | 0.0326 (12) | 0.0030 (9) | 0.0009 (10) | 0.0029 (10) |
C15 | 0.0451 (12) | 0.0323 (11) | 0.0319 (13) | 0.0057 (10) | 0.0031 (10) | −0.0003 (10) |
C16 | 0.0460 (13) | 0.0360 (11) | 0.0284 (12) | 0.0014 (10) | −0.0040 (10) | −0.0029 (10) |
C17 | 0.0375 (12) | 0.0333 (11) | 0.0309 (13) | −0.0013 (9) | −0.0038 (9) | 0.0009 (10) |
O1—C11 | 1.223 (3) | C7—C8 | 1.367 (3) |
N1—C2 | 1.323 (3) | C7—H7 | 0.95 |
N1—C9 | 1.360 (3) | C8—C9 | 1.415 (3) |
N2—C11 | 1.365 (3) | C8—H8 | 0.95 |
N2—C12 | 1.412 (3) | C9—C10 | 1.429 (3) |
N2—H2N | 0.93 (3) | C12—C17 | 1.395 (3) |
C2—C3 | 1.412 (3) | C12—C13 | 1.397 (3) |
C2—C11 | 1.507 (3) | C13—C14 | 1.389 (3) |
C3—C4 | 1.362 (3) | C13—H13 | 0.95 |
C3—H3 | 0.95 | C14—C15 | 1.386 (3) |
C4—C10 | 1.409 (3) | C14—H14 | 0.95 |
C4—H4 | 0.95 | C15—C16 | 1.380 (3) |
C5—C6 | 1.359 (3) | C15—H15 | 0.95 |
C5—C10 | 1.417 (3) | C16—C17 | 1.384 (3) |
C5—H5 | 0.95 | C16—H16 | 0.95 |
C6—C7 | 1.422 (3) | C17—H17 | 0.95 |
C6—H6 | 0.95 | ||
C2—N1—C9 | 118.18 (18) | N1—C9—C10 | 121.76 (19) |
C11—N2—C12 | 128.57 (19) | C8—C9—C10 | 118.2 (2) |
C11—N2—H2N | 114.4 (15) | C4—C10—C5 | 123.5 (2) |
C12—N2—H2N | 117.0 (15) | C4—C10—C9 | 117.7 (2) |
N1—C2—C3 | 124.0 (2) | C5—C10—C9 | 118.9 (2) |
N1—C2—C11 | 117.99 (19) | O1—C11—N2 | 125.5 (2) |
C3—C2—C11 | 117.96 (19) | O1—C11—C2 | 121.12 (19) |
C4—C3—C2 | 118.3 (2) | N2—C11—C2 | 113.41 (19) |
C4—C3—H3 | 120.9 | C17—C12—C13 | 119.5 (2) |
C2—C3—H3 | 120.9 | C17—C12—N2 | 122.81 (19) |
C3—C4—C10 | 120.1 (2) | C13—C12—N2 | 117.7 (2) |
C3—C4—H4 | 120.0 | C14—C13—C12 | 119.9 (2) |
C10—C4—H4 | 120.0 | C14—C13—H13 | 120.1 |
C6—C5—C10 | 121.6 (2) | C12—C13—H13 | 120.1 |
C6—C5—H5 | 119.2 | C15—C14—C13 | 120.6 (2) |
C10—C5—H5 | 119.2 | C15—C14—H14 | 119.7 |
C5—C6—C7 | 119.6 (2) | C13—C14—H14 | 119.7 |
C5—C6—H6 | 120.2 | C16—C15—C14 | 119.2 (2) |
C7—C6—H6 | 120.2 | C16—C15—H15 | 120.4 |
C8—C7—C6 | 120.3 (2) | C14—C15—H15 | 120.4 |
C8—C7—H7 | 119.9 | C15—C16—C17 | 121.4 (2) |
C6—C7—H7 | 119.9 | C15—C16—H16 | 119.3 |
C7—C8—C9 | 121.4 (2) | C17—C16—H16 | 119.3 |
C7—C8—H8 | 119.3 | C16—C17—C12 | 119.5 (2) |
C9—C8—H8 | 119.3 | C16—C17—H17 | 120.2 |
N1—C9—C8 | 120.03 (18) | C12—C17—H17 | 120.2 |
C9—N1—C2—C3 | −0.7 (3) | N1—C9—C10—C5 | −179.29 (19) |
C9—N1—C2—C11 | 177.34 (17) | C8—C9—C10—C5 | 0.2 (3) |
N1—C2—C3—C4 | 1.4 (3) | C12—N2—C11—O1 | 2.3 (4) |
C11—C2—C3—C4 | −176.62 (19) | C12—N2—C11—C2 | −177.88 (19) |
C2—C3—C4—C10 | −0.4 (3) | N1—C2—C11—O1 | −175.35 (19) |
C10—C5—C6—C7 | −0.4 (3) | C3—C2—C11—O1 | 2.8 (3) |
C5—C6—C7—C8 | 0.2 (3) | N1—C2—C11—N2 | 4.8 (3) |
C6—C7—C8—C9 | 0.1 (3) | C3—C2—C11—N2 | −177.08 (19) |
C2—N1—C9—C8 | 179.48 (19) | C11—N2—C12—C17 | 0.6 (3) |
C2—N1—C9—C10 | −1.1 (3) | C11—N2—C12—C13 | −179.2 (2) |
C7—C8—C9—N1 | 179.17 (19) | C17—C12—C13—C14 | 0.4 (3) |
C7—C8—C9—C10 | −0.3 (3) | N2—C12—C13—C14 | −179.69 (19) |
C3—C4—C10—C5 | −179.9 (2) | C12—C13—C14—C15 | −1.0 (3) |
C3—C4—C10—C9 | −1.2 (3) | C13—C14—C15—C16 | 1.0 (3) |
C6—C5—C10—C4 | 178.8 (2) | C14—C15—C16—C17 | −0.5 (3) |
C6—C5—C10—C9 | 0.1 (3) | C15—C16—C17—C12 | −0.1 (3) |
N1—C9—C10—C4 | 2.0 (3) | C13—C12—C17—C16 | 0.1 (3) |
C8—C9—C10—C4 | −178.54 (19) | N2—C12—C17—C16 | −179.76 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···N1 | 0.93 (3) | 2.19 (3) | 2.674 (3) | 111 (2) |
C17—H17···O1 | 0.95 | 2.26 | 2.889 (3) | 123 |
Experimental details
Crystal data | |
Chemical formula | C16H12N2O |
Mr | 248.28 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 153 |
a, b, c (Å) | 16.9856 (19), 12.8279 (16), 5.4455 (7) |
V (Å3) | 1186.5 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.52 × 0.30 × 0.09 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11138, 1494, 1306 |
Rint | 0.069 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.108, 1.01 |
No. of reflections | 1494 |
No. of parameters | 176 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.15, −0.20 |
Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), RAPID-AUTO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Bruker, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···N1 | 0.93 (3) | 2.19 (3) | 2.674 (3) | 111 (2) |
C17—H17···O1 | 0.95 | 2.26 | 2.889 (3) | 123 |
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Quinoline-2-carboxamide compounds are a class of important materials as metal ligands (Perlepes et al., 1986) and as potential radioligands for visualization of peripheral benzodiazepine receptors (Matarrese et al., 2001). We report here the crystal structure of the title compound, (I).
The O1—C11 [1.223 (3) Å], N2—C11 [1.365 (3) Å] and N2—C12 [1.412 (3) Å] bond lengths indicate extensive electron delocalization in the amide linkage. The quinoline ring system is planar within ±0.013 (2) Å. The dihedral angle between the C2/C3/C4/C9/C10/N1 and C2/C11/O1/N2 planes is 4.6 (1)° and that between C2/C11/O1/N2 and C12—C17 planes is 2.5 (1)° (Fig 1). The dihedral angle between the quinoline ring system and phenyl ring is 6.8 (1)°. Weak N—H···N and C—H···O hydrogen bonds are observed in the molecular structure (Table 1).