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Mol­ecules of the title compound, C19H18N2O3·H2O, form inversion-related dimers through C—H...O hydrogen bonds. The crystal packing is further stabilized by inter­molecular N—H...O and C—H...O hydrogen bonds involving the solvent water mol­ecule, and by C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806032260/sj2105sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806032260/sj2105Isup2.hkl
Contains datablock I

CCDC reference: 621496

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.056
  • wR factor = 0.135
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O1W - H1W1 ... ?
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 H2 O
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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).

N-(4-Ethoxyphenyl)-2-(quinolin-8-yloxy)acetamide monohydrate top
Crystal data top
C19H18N2O3·H2OF(000) = 720
Mr = 340.37Dx = 1.309 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 914 reflections
a = 14.603 (2) Åθ = 2.6–20.1°
b = 5.0837 (7) ŵ = 0.09 mm1
c = 24.349 (3) ÅT = 293 K
β = 107.143 (3)°Plate, colourless
V = 1727.3 (4) Å30.37 × 0.12 × 0.08 mm
Z = 4
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
3396 independent reflections
Radiation source: fine-focus sealed tube1758 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
Detector resolution: 8.33 pixels mm-1θmax = 26.1°, θmin = 1.5°
ω scansh = 1418
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 66
Tmin = 0.967, Tmax = 0.993l = 2730
9166 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0527P)2]
where P = (Fo2 + 2Fc2)/3
3396 reflections(Δ/σ)max < 0.001
234 parametersΔρmax = 0.16 e Å3
2 restraintsΔρmin = 0.15 e Å3
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
xyzUiso*/Ueq
N20.27640 (13)0.0936 (4)0.09924 (8)0.0491 (5)
H2A0.28410.01200.12780.059*
O10.15088 (11)0.2661 (3)0.11634 (6)0.0526 (5)
N10.21287 (14)0.5713 (4)0.20933 (8)0.0549 (6)
O20.16904 (14)0.2158 (4)0.01511 (8)0.0832 (7)
C90.12136 (17)0.6071 (5)0.17484 (10)0.0464 (6)
C80.08679 (17)0.4453 (5)0.12540 (10)0.0476 (6)
O30.59795 (13)0.7148 (4)0.11463 (7)0.0735 (6)
C120.35443 (18)0.2621 (5)0.10093 (10)0.0474 (6)
C110.19227 (18)0.0794 (5)0.05842 (11)0.0522 (7)
O1W0.35771 (19)0.2333 (5)0.20483 (9)0.0756 (6)
C70.00523 (18)0.4745 (5)0.09079 (10)0.0572 (7)
H7A0.02810.36700.05880.069*
C150.51489 (19)0.5742 (5)0.10818 (11)0.0554 (7)
C170.35394 (19)0.4441 (5)0.05868 (10)0.0592 (7)
H17A0.29950.46320.02740.071*
C100.11957 (17)0.1170 (5)0.06499 (10)0.0541 (7)
H10A0.06120.02480.06440.065*
H10B0.10460.23600.03240.065*
C30.0968 (2)0.9566 (6)0.23595 (13)0.0711 (8)
H3A0.05871.08610.24520.085*
C40.0600 (2)0.7996 (5)0.18676 (11)0.0527 (7)
C130.43642 (19)0.2433 (5)0.14741 (11)0.0607 (7)
H13A0.43800.12340.17650.073*
C50.0344 (2)0.8254 (5)0.14972 (12)0.0654 (8)
H5A0.07530.95160.15710.078*
C140.51498 (19)0.3972 (5)0.15135 (11)0.0647 (8)
H14A0.56870.38270.18320.078*
C160.43368 (19)0.5982 (5)0.06259 (11)0.0624 (8)
H16A0.43220.71990.03380.075*
C60.0649 (2)0.6648 (6)0.10334 (12)0.0679 (8)
H6A0.12730.68210.07930.081*
C10.2432 (2)0.7233 (5)0.25449 (12)0.0702 (8)
H1B0.30570.70030.27790.084*
C180.6006 (2)0.8963 (6)0.07066 (11)0.0717 (8)
H18A0.55231.03150.06710.086*
H18B0.58810.80630.03410.086*
C20.1872 (2)0.9188 (6)0.26966 (13)0.0789 (9)
H2B0.21221.02040.30240.095*
C190.6990 (2)1.0168 (8)0.08745 (13)0.1054 (12)
H19A0.70321.14230.05880.158*
H19B0.74600.88130.09030.158*
H19C0.71071.10350.12390.158*
H1W10.400 (2)0.342 (7)0.201 (2)0.18 (2)*
H2W10.3090 (17)0.327 (6)0.2054 (15)0.128 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0475 (13)0.0538 (13)0.0422 (12)0.0042 (11)0.0071 (10)0.0063 (10)
O10.0462 (10)0.0584 (11)0.0466 (10)0.0080 (9)0.0034 (8)0.0089 (8)
N10.0551 (14)0.0583 (14)0.0462 (13)0.0053 (12)0.0072 (11)0.0058 (11)
O20.0657 (13)0.1064 (16)0.0627 (13)0.0191 (12)0.0039 (10)0.0369 (12)
C90.0475 (16)0.0482 (15)0.0431 (15)0.0019 (13)0.0130 (12)0.0040 (12)
C80.0472 (16)0.0496 (16)0.0459 (15)0.0053 (14)0.0136 (13)0.0029 (12)
O30.0623 (13)0.0822 (14)0.0664 (13)0.0269 (11)0.0044 (10)0.0082 (10)
C120.0483 (15)0.0508 (16)0.0410 (14)0.0066 (13)0.0101 (12)0.0034 (12)
C110.0484 (16)0.0601 (17)0.0439 (15)0.0023 (14)0.0070 (13)0.0039 (14)
O1W0.0698 (15)0.0767 (15)0.0746 (15)0.0121 (15)0.0121 (12)0.0049 (12)
C70.0501 (16)0.0645 (18)0.0529 (16)0.0040 (14)0.0090 (14)0.0046 (13)
C150.0517 (17)0.0591 (18)0.0498 (16)0.0120 (15)0.0064 (14)0.0030 (14)
C170.0538 (17)0.0674 (18)0.0483 (16)0.0086 (15)0.0024 (13)0.0082 (14)
C100.0490 (15)0.0642 (17)0.0436 (15)0.0023 (15)0.0053 (12)0.0068 (13)
C30.084 (2)0.0623 (19)0.075 (2)0.0025 (18)0.0370 (18)0.0087 (17)
C40.0629 (18)0.0494 (16)0.0507 (16)0.0004 (14)0.0242 (14)0.0037 (13)
C130.0580 (18)0.0646 (18)0.0506 (16)0.0082 (16)0.0023 (14)0.0093 (14)
C50.064 (2)0.069 (2)0.071 (2)0.0154 (16)0.0324 (17)0.0048 (16)
C140.0543 (17)0.0731 (19)0.0546 (17)0.0129 (16)0.0027 (14)0.0073 (15)
C160.0618 (18)0.0657 (19)0.0552 (17)0.0155 (16)0.0104 (15)0.0072 (14)
C60.0487 (17)0.084 (2)0.070 (2)0.0180 (16)0.0151 (15)0.0056 (17)
C10.072 (2)0.076 (2)0.0567 (18)0.0114 (18)0.0101 (16)0.0139 (16)
C180.069 (2)0.085 (2)0.0615 (18)0.0219 (18)0.0195 (15)0.0009 (17)
C20.089 (2)0.081 (2)0.067 (2)0.013 (2)0.0233 (19)0.0290 (18)
C190.079 (2)0.138 (3)0.096 (2)0.051 (2)0.0196 (19)0.008 (2)
Geometric parameters (Å, º) top
N2—C111.335 (3)C17—H17A0.9300
N2—C121.417 (3)C10—H10A0.9700
N2—H2A0.8600C10—H10B0.9700
O1—C81.370 (3)C3—C21.348 (4)
O1—C101.418 (3)C3—C41.407 (3)
N1—C11.310 (3)C3—H3A0.9300
N1—C91.365 (3)C4—C51.414 (4)
O2—C111.223 (3)C13—C141.368 (3)
C9—C41.413 (3)C13—H13A0.9300
C9—C81.422 (3)C5—C61.358 (3)
C8—C71.368 (3)C5—H5A0.9300
O3—C151.377 (3)C14—H14A0.9300
O3—C181.422 (3)C16—H16A0.9300
C12—C171.382 (3)C6—H6A0.9300
C12—C131.387 (3)C1—C21.404 (4)
C11—C101.500 (3)C1—H1B0.9300
O1W—H1W10.85 (3)C18—C191.505 (4)
O1W—H2W10.86 (3)C18—H18A0.9700
C7—C61.395 (3)C18—H18B0.9700
C7—H7A0.9300C2—H2B0.9300
C15—C161.370 (3)C19—H19A0.9600
C15—C141.383 (3)C19—H19B0.9600
C17—C161.383 (3)C19—H19C0.9600
C11—N2—C12127.6 (2)C3—C4—C9117.5 (3)
C11—N2—H2A116.2C3—C4—C5123.1 (3)
C12—N2—H2A116.2C9—C4—C5119.4 (2)
C8—O1—C10116.08 (18)C14—C13—C12121.5 (2)
C1—N1—C9117.7 (2)C14—C13—H13A119.3
N1—C9—C4122.1 (2)C12—C13—H13A119.3
N1—C9—C8118.9 (2)C6—C5—C4119.6 (3)
C4—C9—C8119.1 (2)C6—C5—H5A120.2
C7—C8—O1124.5 (2)C4—C5—H5A120.2
C7—C8—C9119.9 (2)C13—C14—C15120.4 (2)
O1—C8—C9115.6 (2)C13—C14—H14A119.8
C15—O3—C18118.0 (2)C15—C14—H14A119.8
C17—C12—C13117.9 (2)C15—C16—C17121.0 (2)
C17—C12—N2123.8 (2)C15—C16—H16A119.5
C13—C12—N2118.4 (2)C17—C16—H16A119.5
O2—C11—N2124.9 (2)C5—C6—C7121.7 (3)
O2—C11—C10116.4 (2)C5—C6—H6A119.1
N2—C11—C10118.8 (2)C7—C6—H6A119.1
H1W1—O1W—H2W1105 (4)N1—C1—C2124.0 (3)
C8—C7—C6120.3 (2)N1—C1—H1B118.0
C8—C7—H7A119.9C2—C1—H1B118.0
C6—C7—H7A119.9O3—C18—C19107.2 (2)
C16—C15—O3124.7 (2)O3—C18—H18A110.3
C16—C15—C14118.7 (3)C19—C18—H18A110.3
O3—C15—C14116.6 (2)O3—C18—H18B110.3
C12—C17—C16120.5 (2)C19—C18—H18B110.3
C12—C17—H17A119.7H18A—C18—H18B108.5
C16—C17—H17A119.7C3—C2—C1118.9 (3)
O1—C10—C11113.30 (19)C3—C2—H2B120.6
O1—C10—H10A108.9C1—C2—H2B120.6
C11—C10—H10A108.9C18—C19—H19A109.5
O1—C10—H10B108.9C18—C19—H19B109.5
C11—C10—H10B108.9H19A—C19—H19B109.5
H10A—C10—H10B107.7C18—C19—H19C109.5
C2—C3—C4119.8 (3)H19A—C19—H19C109.5
C2—C3—H3A120.1H19B—C19—H19C109.5
C4—C3—H3A120.1
C1—N1—C9—C40.3 (3)C2—C3—C4—C5179.2 (3)
C1—N1—C9—C8179.8 (2)N1—C9—C4—C30.2 (3)
C10—O1—C8—C74.7 (3)C8—C9—C4—C3179.8 (2)
C10—O1—C8—C9175.6 (2)N1—C9—C4—C5179.3 (2)
N1—C9—C8—C7178.8 (2)C8—C9—C4—C50.6 (3)
C4—C9—C8—C71.2 (3)C17—C12—C13—C140.7 (4)
N1—C9—C8—O10.9 (3)N2—C12—C13—C14179.0 (2)
C4—C9—C8—O1179.1 (2)C3—C4—C5—C6179.4 (2)
C11—N2—C12—C170.3 (4)C9—C4—C5—C60.1 (4)
C11—N2—C12—C13179.4 (2)C12—C13—C14—C151.0 (4)
C12—N2—C11—O20.5 (4)C16—C15—C14—C132.2 (4)
C12—N2—C11—C10179.3 (2)O3—C15—C14—C13177.9 (2)
O1—C8—C7—C6179.4 (2)O3—C15—C16—C17178.3 (2)
C9—C8—C7—C60.9 (4)C14—C15—C16—C171.8 (4)
C18—O3—C15—C160.8 (4)C12—C17—C16—C150.1 (4)
C18—O3—C15—C14179.3 (2)C4—C5—C6—C70.4 (4)
C13—C12—C17—C161.1 (4)C8—C7—C6—C50.1 (4)
N2—C12—C17—C16178.5 (2)C9—N1—C1—C20.4 (4)
C8—O1—C10—C11178.7 (2)C15—O3—C18—C19178.6 (2)
O2—C11—C10—O1179.4 (2)C4—C3—C2—C10.5 (5)
N2—C11—C10—O10.7 (3)N1—C1—C2—C30.5 (5)
C2—C3—C4—C90.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10A···Cg2i0.972.823.524130
O1W—H1W1···Cg3ii0.85 (3)2.813.452133
C18—H18A···Cg3i0.972.943.851158
N2—H2A···O10.862.282.707 (3)111
N2—H2A···O1W0.862.182.997 (3)159
O1W—H2W1···N10.86 (3)1.90 (3)2.752 (3)172 (3)
C7—H7A···O2iii0.932.433.235 (3)146
C13—H13A···O1W0.932.373.177 (4)145
C17—H17A···O20.932.232.842 (3)122
Symmetry codes: (i) x, y+1, z; (ii) x, y1, z; (iii) x, y, z.
 

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