Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041498/is6167sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041498/is6167Isup2.hkl |
CCDC reference: 296591
The title compound was prepared according to the literature method of Wen et al. (2005). Colorless single crystals suitable for X-ray diffraction were obtained by slow evaporation of a petroleum ether-ethylacetate (1:3, v/v) solution over 5 d.
All H atoms were located in a difference Fourier map and constrained to ride on their parent atoms, with C—H = 0.93–0.97 Å and N—H = 0.86 Å, and with Uiso(H) = 1.2Ueq(C or N) [Uiso(H) = 1.5Ueq(C) for methyl H atoms].
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C19H18N2O3 | F(000) = 680 |
Mr = 322.35 | Dx = 1.311 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0480 (13) Å | Cell parameters from 4032 reflections |
b = 8.5248 (14) Å | θ = 2.5–25.7° |
c = 23.821 (4) Å | µ = 0.09 mm−1 |
β = 91.676 (2)° | T = 293 K |
V = 1633.6 (5) Å3 | Plate, colourless |
Z = 4 | 0.53 × 0.27 × 0.17 mm |
Siemens SMART 1000 CCD area-detector diffractometer | 3220 independent reflections |
Radiation source: fine-focus sealed tube | 2658 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.1°, θmin = 2.5° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −7→10 |
Tmin = 0.954, Tmax = 0.985 | l = −29→28 |
8662 measured reflections |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0629P)2 + 0.1712P] where P = (Fo2 + 2Fc2)/3 |
3220 reflections | (Δ/σ)max < 0.001 |
217 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C19H18N2O3 | V = 1633.6 (5) Å3 |
Mr = 322.35 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.0480 (13) Å | µ = 0.09 mm−1 |
b = 8.5248 (14) Å | T = 293 K |
c = 23.821 (4) Å | 0.53 × 0.27 × 0.17 mm |
β = 91.676 (2)° |
Siemens SMART 1000 CCD area-detector diffractometer | 3220 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2658 reflections with I > 2σ(I) |
Tmin = 0.954, Tmax = 0.985 | Rint = 0.016 |
8662 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.17 e Å−3 |
3220 reflections | Δρmin = −0.25 e Å−3 |
217 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 | 0.00672 (11) | 0.97193 (11) | 0.17553 (4) | 0.0618 (3) | |
O2 | −0.34476 (13) | 1.04045 (18) | 0.08714 (5) | 0.0981 (4) | |
O3 | 0.12585 (11) | 0.72344 (11) | 0.03623 (4) | 0.0635 (3) | |
N1 | 0.31135 (14) | 0.86038 (14) | 0.19635 (5) | 0.0629 (3) | |
N2 | −0.10480 (12) | 0.90637 (13) | 0.07366 (4) | 0.0545 (3) | |
H2A | −0.0122 | 0.8819 | 0.0904 | 0.065* | |
C1 | 0.46017 (19) | 0.80453 (19) | 0.20778 (7) | 0.0753 (4) | |
H1B | 0.5164 | 0.7578 | 0.1786 | 0.090* | |
C2 | 0.5411 (2) | 0.8098 (2) | 0.26068 (8) | 0.0816 (5) | |
H2B | 0.6467 | 0.7671 | 0.2661 | 0.098* | |
C3 | 0.4622 (2) | 0.87854 (18) | 0.30357 (7) | 0.0759 (4) | |
H3A | 0.5131 | 0.8827 | 0.3391 | 0.091* | |
C4 | 0.30231 (18) | 0.94401 (15) | 0.29442 (6) | 0.0602 (3) | |
C5 | 0.2135 (2) | 1.02087 (18) | 0.33659 (6) | 0.0723 (4) | |
H5A | 0.2605 | 1.0315 | 0.3725 | 0.087* | |
C6 | 0.0597 (2) | 1.07919 (18) | 0.32484 (6) | 0.0731 (4) | |
H6A | 0.0023 | 1.1295 | 0.3530 | 0.088* | |
C7 | −0.01450 (19) | 1.06512 (17) | 0.27099 (6) | 0.0646 (4) | |
H7A | −0.1204 | 1.1053 | 0.2639 | 0.078* | |
C8 | 0.06862 (17) | 0.99234 (14) | 0.22890 (5) | 0.0540 (3) | |
C9 | 0.23151 (16) | 0.93046 (14) | 0.23956 (5) | 0.0534 (3) | |
C10 | −0.15166 (16) | 1.03701 (18) | 0.16219 (6) | 0.0643 (4) | |
H10A | −0.1461 | 1.1503 | 0.1657 | 0.077* | |
H10B | −0.2316 | 0.9987 | 0.1886 | 0.077* | |
C11 | −0.20894 (16) | 0.99435 (17) | 0.10340 (6) | 0.0617 (3) | |
C12 | −0.12822 (14) | 0.84898 (15) | 0.01848 (5) | 0.0511 (3) | |
C13 | −0.26282 (16) | 0.88459 (18) | −0.01681 (6) | 0.0633 (4) | |
H13A | −0.3470 | 0.9491 | −0.0042 | 0.076* | |
C14 | −0.27254 (18) | 0.8247 (2) | −0.07067 (6) | 0.0712 (4) | |
H14A | −0.3629 | 0.8498 | −0.0942 | 0.085* | |
C15 | −0.15032 (18) | 0.72893 (19) | −0.08964 (6) | 0.0708 (4) | |
H15A | −0.1578 | 0.6890 | −0.1260 | 0.085* | |
C16 | −0.01518 (17) | 0.69105 (18) | −0.05485 (6) | 0.0649 (4) | |
H16A | 0.0674 | 0.6249 | −0.0677 | 0.078* | |
C17 | −0.00300 (15) | 0.75117 (15) | −0.00128 (5) | 0.0533 (3) | |
C18 | 0.27288 (17) | 0.65097 (19) | 0.01583 (6) | 0.0661 (4) | |
H18A | 0.3119 | 0.7071 | −0.0167 | 0.079* | |
H18B | 0.2503 | 0.5432 | 0.0050 | 0.079* | |
C19 | 0.40048 (19) | 0.6567 (2) | 0.06267 (7) | 0.0825 (5) | |
H19A | 0.5016 | 0.6091 | 0.0507 | 0.124* | |
H19B | 0.3603 | 0.6007 | 0.0945 | 0.124* | |
H19C | 0.4215 | 0.7639 | 0.0729 | 0.124* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0589 (5) | 0.0722 (6) | 0.0541 (5) | 0.0186 (4) | −0.0015 (4) | −0.0073 (4) |
O2 | 0.0584 (6) | 0.1513 (12) | 0.0840 (8) | 0.0424 (7) | −0.0077 (5) | −0.0205 (7) |
O3 | 0.0577 (5) | 0.0760 (6) | 0.0565 (5) | 0.0223 (4) | −0.0063 (4) | −0.0064 (4) |
N1 | 0.0594 (7) | 0.0646 (7) | 0.0643 (7) | 0.0087 (5) | −0.0043 (5) | −0.0083 (5) |
N2 | 0.0467 (5) | 0.0628 (6) | 0.0540 (6) | 0.0109 (5) | −0.0009 (4) | 0.0020 (5) |
C1 | 0.0642 (9) | 0.0760 (10) | 0.0849 (10) | 0.0137 (8) | −0.0095 (7) | −0.0146 (8) |
C2 | 0.0710 (10) | 0.0728 (10) | 0.0993 (12) | 0.0101 (8) | −0.0260 (9) | −0.0068 (9) |
C3 | 0.0844 (11) | 0.0675 (9) | 0.0742 (10) | −0.0081 (8) | −0.0264 (8) | 0.0033 (8) |
C4 | 0.0725 (8) | 0.0501 (7) | 0.0575 (8) | −0.0146 (6) | −0.0067 (6) | 0.0028 (6) |
C5 | 0.0911 (11) | 0.0734 (9) | 0.0521 (8) | −0.0225 (8) | −0.0016 (7) | −0.0033 (7) |
C6 | 0.0935 (11) | 0.0684 (9) | 0.0581 (8) | −0.0137 (8) | 0.0162 (7) | −0.0130 (7) |
C7 | 0.0722 (9) | 0.0593 (8) | 0.0628 (8) | 0.0020 (6) | 0.0099 (7) | −0.0072 (6) |
C8 | 0.0632 (8) | 0.0481 (6) | 0.0508 (7) | −0.0014 (6) | 0.0023 (5) | −0.0020 (5) |
C9 | 0.0603 (7) | 0.0435 (6) | 0.0563 (7) | −0.0049 (5) | −0.0010 (6) | 0.0004 (5) |
C10 | 0.0557 (8) | 0.0748 (9) | 0.0627 (8) | 0.0160 (6) | 0.0072 (6) | −0.0029 (7) |
C11 | 0.0479 (7) | 0.0744 (9) | 0.0629 (8) | 0.0124 (6) | 0.0047 (6) | 0.0018 (6) |
C12 | 0.0464 (6) | 0.0539 (7) | 0.0530 (7) | −0.0011 (5) | −0.0007 (5) | 0.0041 (5) |
C13 | 0.0476 (7) | 0.0750 (9) | 0.0669 (8) | 0.0068 (6) | −0.0046 (6) | 0.0002 (7) |
C14 | 0.0562 (8) | 0.0887 (10) | 0.0676 (9) | 0.0016 (7) | −0.0159 (6) | 0.0008 (8) |
C15 | 0.0673 (9) | 0.0845 (10) | 0.0600 (8) | −0.0016 (8) | −0.0096 (7) | −0.0086 (7) |
C16 | 0.0622 (8) | 0.0712 (9) | 0.0610 (8) | 0.0078 (7) | −0.0028 (6) | −0.0084 (7) |
C17 | 0.0497 (6) | 0.0551 (7) | 0.0547 (7) | 0.0030 (5) | −0.0037 (5) | 0.0022 (5) |
C18 | 0.0585 (8) | 0.0760 (9) | 0.0637 (8) | 0.0202 (7) | 0.0001 (6) | −0.0035 (7) |
C19 | 0.0635 (9) | 0.1054 (13) | 0.0781 (10) | 0.0254 (8) | −0.0087 (7) | −0.0015 (9) |
O1—C8 | 1.3631 (15) | C7—C8 | 1.3701 (18) |
O1—C10 | 1.4176 (15) | C7—H7A | 0.9300 |
O2—C11 | 1.2142 (16) | C8—C9 | 1.4289 (18) |
O3—C17 | 1.3695 (15) | C10—C11 | 1.506 (2) |
O3—C18 | 1.4324 (15) | C10—H10A | 0.9700 |
N1—C1 | 1.3100 (18) | C10—H10B | 0.9700 |
N1—C9 | 1.3667 (17) | C12—C13 | 1.3853 (17) |
N2—C11 | 1.3422 (16) | C12—C17 | 1.4001 (18) |
N2—C12 | 1.4101 (15) | C13—C14 | 1.381 (2) |
N2—H2A | 0.8600 | C13—H13A | 0.9300 |
C1—C2 | 1.402 (2) | C14—C15 | 1.365 (2) |
C1—H1B | 0.9300 | C14—H14A | 0.9300 |
C2—C3 | 1.352 (2) | C15—C16 | 1.3861 (19) |
C2—H2B | 0.9300 | C15—H15A | 0.9300 |
C3—C4 | 1.413 (2) | C16—C17 | 1.3760 (19) |
C3—H3A | 0.9300 | C16—H16A | 0.9300 |
C4—C5 | 1.411 (2) | C18—C19 | 1.495 (2) |
C4—C9 | 1.4149 (18) | C18—H18A | 0.9700 |
C5—C6 | 1.355 (2) | C18—H18B | 0.9700 |
C5—H5A | 0.9300 | C19—H19A | 0.9600 |
C6—C7 | 1.404 (2) | C19—H19B | 0.9600 |
C6—H6A | 0.9300 | C19—H19C | 0.9600 |
C8—O1—C10 | 117.44 (10) | O1—C10—H10B | 109.4 |
C17—O3—C18 | 118.06 (10) | C11—C10—H10B | 109.4 |
C1—N1—C9 | 116.71 (13) | H10A—C10—H10B | 108.0 |
C11—N2—C12 | 128.12 (11) | O2—C11—N2 | 125.64 (14) |
C11—N2—H2A | 115.9 | O2—C11—C10 | 117.82 (12) |
C12—N2—H2A | 115.9 | N2—C11—C10 | 116.54 (11) |
N1—C1—C2 | 124.95 (15) | C13—C12—C17 | 118.96 (12) |
N1—C1—H1B | 117.5 | C13—C12—N2 | 124.79 (12) |
C2—C1—H1B | 117.5 | C17—C12—N2 | 116.24 (10) |
C3—C2—C1 | 118.46 (15) | C14—C13—C12 | 120.32 (13) |
C3—C2—H2B | 120.8 | C14—C13—H13A | 119.8 |
C1—C2—H2B | 120.8 | C12—C13—H13A | 119.8 |
C2—C3—C4 | 120.02 (14) | C15—C14—C13 | 120.45 (13) |
C2—C3—H3A | 120.0 | C15—C14—H14A | 119.8 |
C4—C3—H3A | 120.0 | C13—C14—H14A | 119.8 |
C5—C4—C3 | 123.45 (14) | C14—C15—C16 | 120.11 (14) |
C5—C4—C9 | 119.78 (14) | C14—C15—H15A | 119.9 |
C3—C4—C9 | 116.77 (14) | C16—C15—H15A | 119.9 |
C6—C5—C4 | 120.11 (14) | C17—C16—C15 | 120.07 (14) |
C6—C5—H5A | 119.9 | C17—C16—H16A | 120.0 |
C4—C5—H5A | 119.9 | C15—C16—H16A | 120.0 |
C5—C6—C7 | 121.26 (14) | O3—C17—C16 | 124.95 (12) |
C5—C6—H6A | 119.4 | O3—C17—C12 | 114.97 (11) |
C7—C6—H6A | 119.4 | C16—C17—C12 | 120.08 (12) |
C8—C7—C6 | 120.23 (14) | O3—C18—C19 | 106.79 (11) |
C8—C7—H7A | 119.9 | O3—C18—H18A | 110.4 |
C6—C7—H7A | 119.9 | C19—C18—H18A | 110.4 |
O1—C8—C7 | 124.58 (13) | O3—C18—H18B | 110.4 |
O1—C8—C9 | 115.28 (11) | C19—C18—H18B | 110.4 |
C7—C8—C9 | 120.15 (12) | H18A—C18—H18B | 108.6 |
N1—C9—C4 | 123.07 (12) | C18—C19—H19A | 109.5 |
N1—C9—C8 | 118.47 (11) | C18—C19—H19B | 109.5 |
C4—C9—C8 | 118.46 (12) | H19A—C19—H19B | 109.5 |
O1—C10—C11 | 111.27 (11) | C18—C19—H19C | 109.5 |
O1—C10—H10A | 109.4 | H19A—C19—H19C | 109.5 |
C11—C10—H10A | 109.4 | H19B—C19—H19C | 109.5 |
C9—N1—C1—C2 | 0.9 (2) | C7—C8—C9—C4 | 1.07 (18) |
N1—C1—C2—C3 | −0.6 (3) | C8—O1—C10—C11 | −175.60 (11) |
C1—C2—C3—C4 | −0.5 (2) | C12—N2—C11—O2 | 0.0 (2) |
C2—C3—C4—C5 | −178.47 (15) | C12—N2—C11—C10 | 179.20 (12) |
C2—C3—C4—C9 | 1.2 (2) | O1—C10—C11—O2 | 178.58 (14) |
C3—C4—C5—C6 | −179.23 (14) | O1—C10—C11—N2 | −0.69 (19) |
C9—C4—C5—C6 | 1.1 (2) | C11—N2—C12—C13 | 4.9 (2) |
C4—C5—C6—C7 | −0.1 (2) | C11—N2—C12—C17 | −176.13 (13) |
C5—C6—C7—C8 | −0.4 (2) | C17—C12—C13—C14 | −0.2 (2) |
C10—O1—C8—C7 | 3.00 (19) | N2—C12—C13—C14 | 178.68 (13) |
C10—O1—C8—C9 | −177.43 (11) | C12—C13—C14—C15 | 0.4 (2) |
C6—C7—C8—O1 | 179.48 (12) | C13—C14—C15—C16 | 0.0 (2) |
C6—C7—C8—C9 | −0.1 (2) | C14—C15—C16—C17 | −0.7 (2) |
C1—N1—C9—C4 | −0.03 (19) | C18—O3—C17—C16 | 12.0 (2) |
C1—N1—C9—C8 | −179.74 (13) | C18—O3—C17—C12 | −167.92 (12) |
C5—C4—C9—N1 | 178.71 (12) | C15—C16—C17—O3 | −178.99 (13) |
C3—C4—C9—N1 | −0.98 (19) | C15—C16—C17—C12 | 0.9 (2) |
C5—C4—C9—C8 | −1.57 (18) | C13—C12—C17—O3 | 179.44 (11) |
C3—C4—C9—C8 | 178.74 (12) | N2—C12—C17—O3 | 0.45 (17) |
O1—C8—C9—N1 | 1.20 (17) | C13—C12—C17—C16 | −0.4 (2) |
C7—C8—C9—N1 | −179.20 (12) | N2—C12—C17—C16 | −179.44 (12) |
O1—C8—C9—C4 | −178.53 (10) | C17—O3—C18—C19 | 171.70 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 2.17 | 2.623 (1) | 112 |
N2—H2A···O3 | 0.86 | 2.19 | 2.602 (1) | 109 |
C13—H13A···O2 | 0.93 | 2.31 | 2.903 (2) | 121 |
C14—H14A···O2i | 0.93 | 2.54 | 3.300 (2) | 139 |
Symmetry code: (i) −x−1, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | C19H18N2O3 |
Mr | 322.35 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 8.0480 (13), 8.5248 (14), 23.821 (4) |
β (°) | 91.676 (2) |
V (Å3) | 1633.6 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.53 × 0.27 × 0.17 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.954, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8662, 3220, 2658 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.115, 1.04 |
No. of reflections | 3220 |
No. of parameters | 217 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.25 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
O1—C8 | 1.3631 (15) | N2—C11 | 1.3422 (16) |
O1—C10 | 1.4176 (15) | N2—C12 | 1.4101 (15) |
O2—C11 | 1.2142 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1 | 0.86 | 2.17 | 2.623 (1) | 112 |
N2—H2A···O3 | 0.86 | 2.19 | 2.602 (1) | 109 |
C13—H13A···O2 | 0.93 | 2.31 | 2.903 (2) | 121 |
C14—H14A···O2i | 0.93 | 2.54 | 3.300 (2) | 139 |
Symmetry code: (i) −x−1, −y+2, −z. |
As part of our studies on amide compounds, the title compound, (I), was synthesized and the structure was determined. The bond lengths (Table 1) are comparable with those in the related compound, N-(4-methoxyphenyl)-2-(quinolin-8-yloxy)acetamide monohydrate, (II) (Wen et al., 2005). The non-H atoms in (I) show a nearly planar conformation, with a dihedral angle of 8.46 (6)° between the benzene ring and the quinoline moiety, while the corresponding value in (II) is 67.06 (7)°. There are three intramolecular hydrogen bonds, viz. N2—H2A···O1, N2—H2A···O3 and C13—H13A···O2, forming two five-membered and one six-membered rings (Fig. 1), which contribute to the planarity of the whole molecule. In the crystal structure, the molecules are linked into a dimer by a C14—H14A···O2i hydrogen bond (symmetry code as in Table 2; Fig. 2).