In the title compound, C
23H
18N
2O
2·H
2O, all bond lengths and angles are within normal ranges. The dihedral angles formed by the two phenyl rings with the quinoline moiety are 61.40 (9) and 85.66 (8)°. The crystal packing is stabilized by intermolecular C—H
O and O—H
O hydrogen bonds involving the solvent water molecule.
Supporting information
CCDC reference: 274382
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.046
- wR factor = 0.120
- Data-to-parameter ratio = 14.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 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
2 ALERT type 4 Improvement, methodology, query or suggestion
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 and DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
N,
N-Diphenyl-2-(quinolin-8-yloxy)acetamide monohydrate
top
Crystal data top
C23H18N2O2·H2O | Z = 2 |
Mr = 372.41 | F(000) = 392 |
Triclinic, P1 | Dx = 1.265 Mg m−3 |
a = 9.1761 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.5962 (8) Å | Cell parameters from 1838 reflections |
c = 11.9113 (10) Å | θ = 2.4–24.9° |
α = 72.526 (1)° | µ = 0.09 mm−1 |
β = 78.339 (2)° | T = 293 K |
γ = 82.942 (2)° | Column, colourless |
V = 977.63 (14) Å3 | 0.40 × 0.20 × 0.09 mm |
Data collection top
Siemens SMART 1000 CCD area-detector diffractometer | 3773 independent reflections |
Radiation source: fine-focus sealed tube | 2805 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.0°, θmin = 1.8° |
ω scans | h = −8→11 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −11→11 |
Tmin = 0.967, Tmax = 0.992 | l = −14→14 |
5557 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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0501P)2 + 0.1798P] where P = (Fo2 + 2Fc2)/3 |
3773 reflections | (Δ/σ)max < 0.001 |
261 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1W | 0.30556 (17) | 0.93225 (17) | 0.29003 (14) | 0.0662 (4) | |
O1 | 0.28476 (14) | 0.76932 (11) | 0.10840 (9) | 0.0528 (3) | |
O2 | 0.31292 (17) | 1.05779 (13) | 0.04280 (11) | 0.0683 (4) | |
N1 | 0.2287 (2) | 0.63528 (16) | 0.34335 (13) | 0.0676 (5) | |
N2 | 0.25780 (16) | 1.08670 (14) | −0.13910 (12) | 0.0470 (3) | |
C1 | 0.1992 (3) | 0.5678 (3) | 0.45843 (19) | 0.0947 (8) | |
H1B | 0.1835 | 0.6249 | 0.5111 | 0.114* | |
C2 | 0.1899 (4) | 0.4178 (3) | 0.5069 (2) | 0.1048 (9) | |
H2A | 0.1668 | 0.3766 | 0.5892 | 0.126* | |
C3 | 0.2152 (3) | 0.3332 (2) | 0.4319 (2) | 0.0858 (7) | |
H3A | 0.2105 | 0.2323 | 0.4625 | 0.103* | |
C4 | 0.2488 (2) | 0.39689 (18) | 0.30709 (18) | 0.0600 (5) | |
C5 | 0.2772 (2) | 0.3146 (2) | 0.2235 (2) | 0.0689 (6) | |
H5A | 0.2740 | 0.2133 | 0.2499 | 0.083* | |
C6 | 0.3090 (2) | 0.3831 (2) | 0.1052 (2) | 0.0668 (5) | |
H6A | 0.3276 | 0.3281 | 0.0509 | 0.080* | |
C7 | 0.3144 (2) | 0.53633 (19) | 0.06318 (17) | 0.0567 (5) | |
H7A | 0.3376 | 0.5813 | −0.0185 | 0.068* | |
C8 | 0.28594 (18) | 0.61947 (16) | 0.14108 (15) | 0.0464 (4) | |
C9 | 0.2532 (2) | 0.55117 (17) | 0.26645 (16) | 0.0511 (4) | |
C10 | 0.3087 (2) | 0.84013 (17) | −0.01566 (14) | 0.0513 (4) | |
H10A | 0.2361 | 0.8126 | −0.0527 | 0.062* | |
H10B | 0.4076 | 0.8115 | −0.0524 | 0.062* | |
C11 | 0.2933 (2) | 1.00386 (17) | −0.03303 (14) | 0.0483 (4) | |
C12 | 0.24529 (19) | 1.24465 (17) | −0.16407 (14) | 0.0458 (4) | |
C13 | 0.1121 (2) | 1.3150 (2) | −0.12962 (18) | 0.0639 (5) | |
H13A | 0.0305 | 1.2613 | −0.0877 | 0.077* | |
C14 | 0.0993 (2) | 1.4658 (2) | −0.1572 (2) | 0.0719 (6) | |
H14A | 0.0088 | 1.5137 | −0.1344 | 0.086* | |
C15 | 0.2186 (3) | 1.5446 (2) | −0.21765 (19) | 0.0675 (6) | |
H15A | 0.2097 | 1.6462 | −0.2360 | 0.081* | |
C16 | 0.3517 (3) | 1.4747 (2) | −0.2515 (2) | 0.0730 (6) | |
H16A | 0.4331 | 1.5290 | −0.2927 | 0.088* | |
C17 | 0.3663 (2) | 1.3234 (2) | −0.22480 (18) | 0.0622 (5) | |
H17A | 0.4569 | 1.2758 | −0.2478 | 0.075* | |
C18 | 0.2342 (2) | 1.02765 (17) | −0.23211 (14) | 0.0466 (4) | |
C19 | 0.0911 (2) | 1.0211 (2) | −0.24861 (17) | 0.0618 (5) | |
H19A | 0.0102 | 1.0523 | −0.1989 | 0.074* | |
C20 | 0.0677 (3) | 0.9685 (2) | −0.3388 (2) | 0.0717 (6) | |
H20A | −0.0290 | 0.9642 | −0.3498 | 0.086* | |
C21 | 0.1852 (3) | 0.9229 (2) | −0.41182 (18) | 0.0695 (6) | |
H21A | 0.1688 | 0.8877 | −0.4726 | 0.083* | |
C22 | 0.3276 (3) | 0.9286 (2) | −0.39610 (17) | 0.0695 (6) | |
H22A | 0.4076 | 0.8964 | −0.4459 | 0.083* | |
C23 | 0.3537 (2) | 0.9824 (2) | −0.30596 (16) | 0.0587 (5) | |
H23A | 0.4507 | 0.9875 | −0.2960 | 0.070* | |
H2W1 | 0.276 (3) | 0.842 (3) | 0.305 (2) | 0.098 (8)* | |
H1W1 | 0.301 (3) | 0.971 (3) | 0.213 (2) | 0.104 (9)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1W | 0.0975 (11) | 0.0508 (8) | 0.0569 (9) | −0.0113 (7) | −0.0207 (8) | −0.0177 (7) |
O1 | 0.0873 (9) | 0.0296 (6) | 0.0420 (6) | −0.0071 (5) | −0.0170 (6) | −0.0061 (5) |
O2 | 0.1233 (12) | 0.0388 (7) | 0.0488 (7) | −0.0092 (7) | −0.0309 (7) | −0.0095 (6) |
N1 | 0.1104 (14) | 0.0461 (9) | 0.0464 (9) | −0.0169 (8) | −0.0201 (9) | −0.0045 (7) |
N2 | 0.0621 (9) | 0.0353 (7) | 0.0433 (7) | −0.0043 (6) | −0.0146 (6) | −0.0068 (6) |
C1 | 0.168 (3) | 0.0669 (14) | 0.0498 (12) | −0.0308 (15) | −0.0248 (14) | −0.0039 (11) |
C2 | 0.178 (3) | 0.0722 (16) | 0.0579 (14) | −0.0378 (17) | −0.0339 (16) | 0.0119 (12) |
C3 | 0.120 (2) | 0.0454 (11) | 0.0823 (16) | −0.0213 (12) | −0.0372 (14) | 0.0155 (11) |
C4 | 0.0690 (12) | 0.0354 (9) | 0.0733 (13) | −0.0076 (8) | −0.0276 (10) | −0.0005 (9) |
C5 | 0.0736 (13) | 0.0302 (9) | 0.1028 (17) | −0.0031 (8) | −0.0261 (12) | −0.0120 (10) |
C6 | 0.0737 (13) | 0.0430 (10) | 0.0920 (16) | −0.0016 (9) | −0.0170 (11) | −0.0306 (11) |
C7 | 0.0685 (12) | 0.0426 (10) | 0.0625 (11) | −0.0026 (8) | −0.0135 (9) | −0.0193 (8) |
C8 | 0.0557 (10) | 0.0312 (8) | 0.0539 (10) | −0.0043 (7) | −0.0180 (8) | −0.0086 (7) |
C9 | 0.0633 (11) | 0.0357 (9) | 0.0551 (10) | −0.0059 (7) | −0.0227 (8) | −0.0051 (7) |
C10 | 0.0724 (12) | 0.0393 (9) | 0.0419 (9) | −0.0044 (8) | −0.0134 (8) | −0.0085 (7) |
C11 | 0.0631 (11) | 0.0377 (9) | 0.0433 (9) | −0.0063 (7) | −0.0098 (8) | −0.0088 (7) |
C12 | 0.0569 (10) | 0.0380 (9) | 0.0419 (9) | −0.0028 (7) | −0.0151 (7) | −0.0062 (7) |
C13 | 0.0605 (12) | 0.0499 (11) | 0.0759 (13) | −0.0054 (9) | −0.0040 (10) | −0.0143 (9) |
C14 | 0.0714 (14) | 0.0520 (12) | 0.0915 (15) | 0.0081 (10) | −0.0190 (11) | −0.0209 (11) |
C15 | 0.0926 (16) | 0.0363 (9) | 0.0753 (13) | −0.0015 (10) | −0.0353 (12) | −0.0060 (9) |
C16 | 0.0785 (15) | 0.0477 (11) | 0.0855 (15) | −0.0201 (10) | −0.0147 (11) | −0.0014 (10) |
C17 | 0.0568 (11) | 0.0508 (11) | 0.0737 (13) | −0.0058 (8) | −0.0101 (9) | −0.0099 (9) |
C18 | 0.0613 (11) | 0.0377 (8) | 0.0398 (9) | −0.0078 (7) | −0.0123 (8) | −0.0054 (7) |
C19 | 0.0614 (12) | 0.0630 (12) | 0.0638 (12) | −0.0019 (9) | −0.0186 (9) | −0.0179 (9) |
C20 | 0.0851 (15) | 0.0654 (13) | 0.0738 (14) | −0.0079 (11) | −0.0391 (12) | −0.0157 (11) |
C21 | 0.1141 (19) | 0.0474 (11) | 0.0531 (11) | −0.0161 (11) | −0.0298 (12) | −0.0091 (9) |
C22 | 0.0982 (17) | 0.0555 (12) | 0.0514 (11) | −0.0148 (11) | 0.0047 (11) | −0.0178 (9) |
C23 | 0.0645 (12) | 0.0548 (11) | 0.0553 (11) | −0.0133 (9) | −0.0026 (9) | −0.0146 (9) |
Geometric parameters (Å, º) top
O1W—H2W1 | 0.90 (3) | C10—C11 | 1.514 (2) |
O1W—H1W1 | 0.89 (3) | C10—H10A | 0.9700 |
O1—C8 | 1.3716 (18) | C10—H10B | 0.9700 |
O1—C10 | 1.4128 (19) | C12—C17 | 1.371 (2) |
O2—C11 | 1.2188 (19) | C12—C13 | 1.371 (3) |
N1—C1 | 1.316 (3) | C13—C14 | 1.380 (3) |
N1—C9 | 1.363 (2) | C13—H13A | 0.9300 |
N2—C11 | 1.354 (2) | C14—C15 | 1.359 (3) |
N2—C12 | 1.449 (2) | C14—H14A | 0.9300 |
N2—C18 | 1.449 (2) | C15—C16 | 1.366 (3) |
C1—C2 | 1.387 (3) | C15—H15A | 0.9300 |
C1—H1B | 0.9300 | C16—C17 | 1.386 (3) |
C2—C3 | 1.348 (3) | C16—H16A | 0.9300 |
C2—H2A | 0.9300 | C17—H17A | 0.9300 |
C3—C4 | 1.412 (3) | C18—C19 | 1.378 (2) |
C3—H3A | 0.9300 | C18—C23 | 1.374 (2) |
C4—C5 | 1.414 (3) | C19—C20 | 1.379 (3) |
C4—C9 | 1.416 (2) | C19—H19A | 0.9300 |
C5—C6 | 1.351 (3) | C20—C21 | 1.358 (3) |
C5—H5A | 0.9300 | C20—H20A | 0.9300 |
C6—C7 | 1.408 (2) | C21—C22 | 1.366 (3) |
C6—H6A | 0.9300 | C21—H21A | 0.9300 |
C7—C8 | 1.364 (2) | C22—C23 | 1.394 (3) |
C7—H7A | 0.9300 | C22—H22A | 0.9300 |
C8—C9 | 1.424 (2) | C23—H23A | 0.9300 |
| | | |
H2W1—O1W—H1W1 | 102 (2) | O2—C11—N2 | 122.12 (15) |
C8—O1—C10 | 116.23 (12) | O2—C11—C10 | 122.33 (15) |
C1—N1—C9 | 117.44 (17) | N2—C11—C10 | 115.55 (14) |
C11—N2—C12 | 118.94 (13) | C17—C12—C13 | 120.28 (16) |
C11—N2—C18 | 124.10 (13) | C17—C12—N2 | 119.63 (15) |
C12—N2—C18 | 116.95 (12) | C13—C12—N2 | 120.08 (15) |
N1—C1—C2 | 124.8 (2) | C12—C13—C14 | 119.86 (18) |
N1—C1—H1B | 117.6 | C12—C13—H13A | 120.1 |
C2—C1—H1B | 117.6 | C14—C13—H13A | 120.1 |
C1—C2—C3 | 118.3 (2) | C15—C14—C13 | 120.2 (2) |
C1—C2—H2A | 120.8 | C15—C14—H14A | 119.9 |
C3—C2—H2A | 120.8 | C13—C14—H14A | 119.9 |
C2—C3—C4 | 120.44 (19) | C14—C15—C16 | 120.03 (18) |
C2—C3—H3A | 119.8 | C14—C15—H15A | 120.0 |
C4—C3—H3A | 119.8 | C16—C15—H15A | 120.0 |
C3—C4—C5 | 123.35 (18) | C15—C16—C17 | 120.49 (19) |
C3—C4—C9 | 116.88 (18) | C15—C16—H16A | 119.8 |
C5—C4—C9 | 119.78 (18) | C17—C16—H16A | 119.8 |
C6—C5—C4 | 120.08 (17) | C12—C17—C16 | 119.12 (18) |
C6—C5—H5A | 120.0 | C12—C17—H17A | 120.4 |
C4—C5—H5A | 120.0 | C16—C17—H17A | 120.4 |
C5—C6—C7 | 120.95 (18) | C19—C18—C23 | 120.00 (16) |
C5—C6—H6A | 119.5 | C19—C18—N2 | 119.65 (16) |
C7—C6—H6A | 119.5 | C23—C18—N2 | 120.32 (16) |
C8—C7—C6 | 120.64 (18) | C18—C19—C20 | 120.0 (2) |
C8—C7—H7A | 119.7 | C18—C19—H19A | 120.0 |
C6—C7—H7A | 119.7 | C20—C19—H19A | 120.0 |
C7—C8—O1 | 124.79 (15) | C21—C20—C19 | 120.3 (2) |
C7—C8—C9 | 120.04 (15) | C21—C20—H20A | 119.8 |
O1—C8—C9 | 115.17 (14) | C19—C20—H20A | 119.8 |
N1—C9—C8 | 119.40 (14) | C20—C21—C22 | 120.11 (19) |
N1—C9—C4 | 122.09 (16) | C20—C21—H21A | 119.9 |
C8—C9—C4 | 118.51 (16) | C22—C21—H21A | 119.9 |
O1—C10—C11 | 108.15 (13) | C21—C22—C23 | 120.5 (2) |
O1—C10—H10A | 110.1 | C21—C22—H22A | 119.8 |
C11—C10—H10A | 110.1 | C23—C22—H22A | 119.8 |
O1—C10—H10B | 110.1 | C18—C23—C22 | 119.03 (19) |
C11—C10—H10B | 110.1 | C18—C23—H23A | 120.5 |
H10A—C10—H10B | 108.4 | C22—C23—H23A | 120.5 |
| | | |
C9—N1—C1—C2 | −0.7 (4) | C18—N2—C11—C10 | 0.4 (2) |
N1—C1—C2—C3 | 1.2 (5) | O1—C10—C11—O2 | 24.3 (2) |
C1—C2—C3—C4 | −0.6 (4) | O1—C10—C11—N2 | −156.44 (15) |
C2—C3—C4—C5 | 179.7 (2) | C11—N2—C12—C17 | 93.7 (2) |
C2—C3—C4—C9 | −0.4 (3) | C18—N2—C12—C17 | −84.9 (2) |
C3—C4—C5—C6 | −179.8 (2) | C11—N2—C12—C13 | −87.8 (2) |
C9—C4—C5—C6 | 0.3 (3) | C18—N2—C12—C13 | 93.48 (19) |
C4—C5—C6—C7 | 0.0 (3) | C17—C12—C13—C14 | 0.7 (3) |
C5—C6—C7—C8 | −0.7 (3) | N2—C12—C13—C14 | −177.77 (17) |
C6—C7—C8—O1 | −178.22 (16) | C12—C13—C14—C15 | −0.5 (3) |
C6—C7—C8—C9 | 1.2 (3) | C13—C14—C15—C16 | 0.1 (3) |
C10—O1—C8—C7 | 2.9 (2) | C14—C15—C16—C17 | 0.1 (3) |
C10—O1—C8—C9 | −176.59 (15) | C13—C12—C17—C16 | −0.4 (3) |
C1—N1—C9—C8 | −179.8 (2) | N2—C12—C17—C16 | 178.00 (17) |
C1—N1—C9—C4 | −0.5 (3) | C15—C16—C17—C12 | 0.1 (3) |
C7—C8—C9—N1 | 178.37 (17) | C11—N2—C18—C19 | 103.3 (2) |
O1—C8—C9—N1 | −2.2 (2) | C12—N2—C18—C19 | −78.12 (19) |
C7—C8—C9—C4 | −0.9 (3) | C11—N2—C18—C23 | −78.7 (2) |
O1—C8—C9—C4 | 178.53 (15) | C12—N2—C18—C23 | 99.91 (18) |
C3—C4—C9—N1 | 1.0 (3) | C23—C18—C19—C20 | 0.3 (3) |
C5—C4—C9—N1 | −179.09 (18) | N2—C18—C19—C20 | 178.38 (16) |
C3—C4—C9—C8 | −179.68 (18) | C18—C19—C20—C21 | 0.0 (3) |
C5—C4—C9—C8 | 0.2 (3) | C19—C20—C21—C22 | 0.1 (3) |
C8—O1—C10—C11 | 176.34 (14) | C20—C21—C22—C23 | −0.6 (3) |
C12—N2—C11—O2 | 1.1 (3) | C19—C18—C23—C22 | −0.8 (3) |
C18—N2—C11—O2 | 179.66 (17) | N2—C18—C23—C22 | −178.80 (15) |
C12—N2—C11—C10 | −178.20 (15) | C21—C22—C23—C18 | 0.9 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O2 | 0.89 (2) | 1.93 (2) | 2.817 (2) | 174 (3) |
O1W—H2W1···N1 | 0.89 (3) | 1.98 (3) | 2.872 (2) | 175 (3) |
C5—H5A···O1Wi | 0.93 | 2.58 | 3.502 (3) | 169 |
C23—H23A···O1Wii | 0.93 | 2.47 | 3.383 (3) | 166 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+2, −z. |