N-(4-Methoxy­phen­yl)-2-(quinolin-8-yl­oxy)acetamide monohydrate

In the title compound, C₁₈H₁₆N₂O₃·H₂O, all bond lengths and angles are within normal ranges. The dihedral angle formed by the benzene ring with the quinoline moiety is 67.06 (7)°. Mol­ecules are linked into chains along the a axis by inter­molecular N—H...O, O—H...O and O—H...N hydrogen bonds involving the solvent water mol­ecule. The packing is further stabilized by π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.032
• wR factor = 0.083
• Data-to-parameter ratio = 8.4

checkCIF/PLATON results

No syntax errors found



Alert level C
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

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           26.12
           From the CIF: _reflns_number_total               1901
           Count of symmetry unique reflns         1901
           Completeness (_total/calc)            100.00%
           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

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

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).

N-(4-Methoxyphenyl)-2-(quinolin-8-yloxy)acetamide monohydrate

Crystal data

C18H16N2O3·H2O	Dx = 1.324 Mg m^−3
Mr = 326.34	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 4023 reflections
a = 6.8814 (13) Å	θ = 2.6–25.8°
b = 11.627 (2) Å	µ = 0.10 mm^−1
c = 20.468 (4) Å	T = 293 K
V = 1637.6 (5) Å^3	Block, yellow
Z = 4	0.42 × 0.42 × 0.12 mm
F(000) = 688

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	1901 independent reflections
Radiation source: fine-focus sealed tube	1737 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 8.33 pixels mm^-1	θmax = 26.1°, θmin = 2.0°
ω scans	h = −8→8
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996)	k = −13→14
Tmin = 0.961, Tmax = 0.989	l = −25→24
9310 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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0392P)^2 + 0.1826P] where P = (Fo^2 + 2Fc^2)/3
1901 reflections	(Δ/σ)max < 0.001
225 parameters	Δρmax = 0.13 e Å^−3
0 restraints	Δρmin = −0.14 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.5070 (2)	0.30040 (11)	0.12647 (7)	0.0486 (3)
O2	0.5518 (2)	0.14331 (14)	0.03006 (8)	0.0584 (4)
O3	0.1937 (3)	−0.28656 (13)	−0.11860 (9)	0.0742 (5)
N1	0.8061 (3)	0.33175 (15)	0.20756 (8)	0.0523 (4)
N2	0.2265 (2)	0.11168 (14)	0.03242 (8)	0.0454 (4)
H2A	0.1188	0.1369	0.0482	0.054*
C1	0.9512 (4)	0.3467 (2)	0.24895 (12)	0.0664 (6)
H1B	1.0494	0.2917	0.2498	0.080*
C2	0.9658 (4)	0.4407 (3)	0.29174 (13)	0.0773 (8)
H2B	1.0706	0.4473	0.3202	0.093*
C3	0.8244 (4)	0.5213 (2)	0.29076 (11)	0.0697 (7)
H3A	0.8326	0.5846	0.3184	0.084*
C4	0.6653 (3)	0.51043 (19)	0.24838 (10)	0.0553 (5)
C5	0.5120 (5)	0.5907 (2)	0.24535 (12)	0.0690 (7)
H5A	0.5134	0.6548	0.2725	0.083*
C6	0.3635 (4)	0.5749 (2)	0.20333 (13)	0.0703 (7)
H6A	0.2637	0.6287	0.2016	0.084*
C7	0.3574 (3)	0.47767 (18)	0.16197 (11)	0.0579 (5)
H7A	0.2541	0.4682	0.1332	0.069*
C8	0.5015 (3)	0.39808 (16)	0.16394 (9)	0.0443 (4)
C9	0.6618 (3)	0.41160 (17)	0.20715 (9)	0.0453 (4)
C10	0.3493 (3)	0.28254 (17)	0.08303 (10)	0.0465 (5)
H10A	0.3391	0.3463	0.0527	0.056*
H10B	0.2285	0.2769	0.1072	0.056*
C11	0.3877 (3)	0.17166 (17)	0.04633 (9)	0.0428 (4)
C12	0.2180 (3)	0.00978 (16)	−0.00620 (9)	0.0430 (4)
C13	0.3472 (3)	−0.01060 (18)	−0.05680 (10)	0.0515 (5)
H13A	0.4429	0.0432	−0.0665	0.062*
C14	0.3339 (3)	−0.1105 (2)	−0.09271 (10)	0.0562 (5)
H14A	0.4227	−0.1244	−0.1260	0.067*
C15	0.1905 (3)	−0.19013 (18)	−0.07982 (10)	0.0535 (5)
C16	0.0603 (4)	−0.16979 (19)	−0.03088 (12)	0.0626 (6)
H16A	−0.0372	−0.2229	−0.0220	0.075*
C17	0.0741 (3)	−0.0687 (2)	0.00581 (11)	0.0581 (6)
H17A	−0.0156	−0.0546	0.0388	0.070*
C18	0.0467 (5)	−0.3693 (3)	−0.10819 (18)	0.1047 (12)
H18A	0.0647	−0.4324	−0.1378	0.157*
H18B	−0.0782	−0.3349	−0.1157	0.157*
H18C	0.0537	−0.3968	−0.0640	0.157*
O1W	0.8846 (2)	0.16989 (18)	0.10397 (9)	0.0692 (5)
H2W1	0.783 (4)	0.156 (2)	0.0831 (13)	0.069 (8)*
H1W1	0.855 (4)	0.218 (3)	0.1351 (15)	0.087 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0467 (7)	0.0461 (7)	0.0531 (8)	0.0047 (6)	−0.0116 (6)	−0.0103 (6)
O2	0.0389 (7)	0.0673 (9)	0.0689 (9)	−0.0037 (7)	0.0032 (7)	−0.0219 (8)
O3	0.0815 (12)	0.0569 (9)	0.0842 (11)	−0.0127 (9)	0.0076 (10)	−0.0224 (9)
N1	0.0490 (9)	0.0586 (10)	0.0495 (9)	−0.0035 (9)	−0.0061 (8)	0.0001 (8)
N2	0.0356 (8)	0.0507 (9)	0.0498 (9)	0.0004 (7)	0.0009 (7)	−0.0090 (8)
C1	0.0558 (14)	0.0821 (16)	0.0614 (14)	−0.0042 (13)	−0.0118 (12)	0.0028 (12)
C2	0.0680 (16)	0.108 (2)	0.0556 (13)	−0.0236 (17)	−0.0151 (13)	−0.0056 (14)
C3	0.0801 (17)	0.0794 (16)	0.0495 (12)	−0.0267 (15)	−0.0015 (13)	−0.0148 (12)
C4	0.0657 (14)	0.0573 (12)	0.0427 (11)	−0.0170 (12)	0.0067 (10)	−0.0068 (9)
C5	0.0877 (17)	0.0554 (13)	0.0641 (14)	−0.0026 (14)	0.0103 (14)	−0.0217 (11)
C6	0.0714 (16)	0.0558 (13)	0.0839 (16)	0.0128 (13)	0.0029 (15)	−0.0183 (12)
C7	0.0528 (12)	0.0546 (12)	0.0662 (13)	0.0057 (11)	−0.0029 (11)	−0.0097 (11)
C8	0.0491 (11)	0.0406 (9)	0.0432 (10)	−0.0051 (9)	0.0025 (9)	−0.0035 (8)
C9	0.0497 (11)	0.0473 (10)	0.0388 (9)	−0.0076 (10)	0.0048 (9)	0.0002 (8)
C10	0.0411 (10)	0.0481 (11)	0.0502 (10)	−0.0001 (9)	−0.0062 (9)	−0.0057 (9)
C11	0.0393 (10)	0.0483 (10)	0.0409 (10)	−0.0017 (8)	−0.0023 (8)	−0.0017 (8)
C12	0.0387 (10)	0.0473 (10)	0.0429 (9)	−0.0026 (9)	−0.0035 (8)	−0.0011 (8)
C13	0.0503 (11)	0.0543 (11)	0.0499 (10)	−0.0134 (10)	0.0067 (9)	−0.0047 (9)
C14	0.0544 (12)	0.0624 (13)	0.0517 (11)	−0.0042 (11)	0.0084 (10)	−0.0099 (10)
C15	0.0578 (12)	0.0483 (11)	0.0543 (11)	−0.0032 (11)	−0.0048 (10)	−0.0048 (9)
C16	0.0605 (14)	0.0574 (13)	0.0700 (14)	−0.0222 (12)	0.0090 (12)	−0.0079 (11)
C17	0.0505 (13)	0.0662 (14)	0.0575 (12)	−0.0131 (11)	0.0114 (10)	−0.0093 (11)
C18	0.105 (2)	0.0748 (18)	0.135 (3)	−0.0357 (18)	0.018 (2)	−0.0423 (19)
O1W	0.0404 (8)	0.0969 (14)	0.0703 (11)	0.0152 (9)	−0.0045 (8)	−0.0230 (10)

Geometric parameters (Å, º)

O1—C8	1.371 (2)	C7—C8	1.357 (3)
O1—C10	1.418 (2)	C7—H7A	0.9300
O2—C11	1.223 (2)	C8—C9	1.422 (3)
O3—C15	1.374 (2)	C10—C11	1.515 (3)
O3—C18	1.412 (3)	C10—H10A	0.9700
N1—C1	1.321 (3)	C10—H10B	0.9700
N1—C9	1.359 (3)	C12—C17	1.369 (3)
N2—C11	1.340 (2)	C12—C13	1.385 (3)
N2—C12	1.426 (2)	C13—C14	1.378 (3)
N2—H2A	0.8600	C13—H13A	0.9300
C1—C2	1.404 (4)	C14—C15	1.378 (3)
C1—H1B	0.9300	C14—H14A	0.9300
C2—C3	1.352 (4)	C15—C16	1.365 (3)
C2—H2B	0.9300	C16—C17	1.398 (3)
C3—C4	1.402 (3)	C16—H16A	0.9300
C3—H3A	0.9300	C17—H17A	0.9300
C4—C5	1.409 (4)	C18—H18A	0.9600
C4—C9	1.426 (3)	C18—H18B	0.9600
C5—C6	1.348 (4)	C18—H18C	0.9600
C5—H5A	0.9300	O1W—H2W1	0.84 (3)
C6—C7	1.413 (3)	O1W—H1W1	0.88 (3)
C6—H6A	0.9300
C8—O1—C10	116.82 (14)	O1—C10—H10A	110.2
C15—O3—C18	117.2 (2)	C11—C10—H10A	110.2
C1—N1—C9	117.82 (19)	O1—C10—H10B	110.2
C11—N2—C12	125.76 (16)	C11—C10—H10B	110.2
C11—N2—H2A	117.1	H10A—C10—H10B	108.5
C12—N2—H2A	117.1	O2—C11—N2	124.47 (18)
N1—C1—C2	123.8 (3)	O2—C11—C10	121.69 (17)
N1—C1—H1B	118.1	N2—C11—C10	113.82 (16)
C2—C1—H1B	118.1	C17—C12—C13	118.97 (19)
C3—C2—C1	118.7 (2)	C17—C12—N2	118.98 (17)
C3—C2—H2B	120.7	C13—C12—N2	122.02 (18)
C1—C2—H2B	120.7	C14—C13—C12	120.0 (2)
C2—C3—C4	120.6 (2)	C14—C13—H13A	120.0
C2—C3—H3A	119.7	C12—C13—H13A	120.0
C4—C3—H3A	119.7	C13—C14—C15	120.8 (2)
C3—C4—C5	123.5 (2)	C13—C14—H14A	119.6
C3—C4—C9	116.9 (2)	C15—C14—H14A	119.6
C5—C4—C9	119.6 (2)	C16—C15—O3	125.1 (2)
C6—C5—C4	120.4 (2)	C16—C15—C14	119.61 (19)
C6—C5—H5A	119.8	O3—C15—C14	115.24 (19)
C4—C5—H5A	119.8	C15—C16—C17	119.7 (2)
C5—C6—C7	120.9 (2)	C15—C16—H16A	120.2
C5—C6—H6A	119.6	C17—C16—H16A	120.2
C7—C6—H6A	119.6	C12—C17—C16	120.9 (2)
C8—C7—C6	120.4 (2)	C12—C17—H17A	119.6
C8—C7—H7A	119.8	C16—C17—H17A	119.6
C6—C7—H7A	119.8	O3—C18—H18A	109.5
C7—C8—O1	124.63 (18)	O3—C18—H18B	109.5
C7—C8—C9	120.64 (17)	H18A—C18—H18B	109.5
O1—C8—C9	114.73 (17)	O3—C18—H18C	109.5
N1—C9—C8	119.65 (16)	H18A—C18—H18C	109.5
N1—C9—C4	122.29 (18)	H18B—C18—H18C	109.5
C8—C9—C4	118.06 (19)	H2W1—O1W—H1W1	107 (3)
O1—C10—C11	107.59 (15)
C9—N1—C1—C2	−0.8 (3)	C3—C4—C9—C8	179.66 (19)
N1—C1—C2—C3	−0.3 (4)	C5—C4—C9—C8	0.1 (3)
C1—C2—C3—C4	0.8 (4)	C8—O1—C10—C11	179.08 (15)
C2—C3—C4—C5	179.3 (2)	C12—N2—C11—O2	−3.7 (3)
C2—C3—C4—C9	−0.2 (3)	C12—N2—C11—C10	174.42 (16)
C3—C4—C5—C6	179.9 (2)	O1—C10—C11—O2	−36.1 (3)
C9—C4—C5—C6	−0.6 (4)	O1—C10—C11—N2	145.67 (17)
C4—C5—C6—C7	0.5 (4)	C11—N2—C12—C17	151.5 (2)
C5—C6—C7—C8	0.1 (4)	C11—N2—C12—C13	−30.5 (3)
C6—C7—C8—O1	179.0 (2)	C17—C12—C13—C14	−2.2 (3)
C6—C7—C8—C9	−0.6 (3)	N2—C12—C13—C14	179.76 (19)
C10—O1—C8—C7	−0.2 (3)	C12—C13—C14—C15	1.3 (3)
C10—O1—C8—C9	179.42 (16)	C18—O3—C15—C16	2.1 (4)
C1—N1—C9—C8	−179.21 (19)	C18—O3—C15—C14	−178.6 (2)
C1—N1—C9—C4	1.4 (3)	C13—C14—C15—C16	−0.1 (3)
C7—C8—C9—N1	−178.94 (19)	C13—C14—C15—O3	−179.5 (2)
O1—C8—C9—N1	1.4 (2)	O3—C15—C16—C17	179.1 (2)
C7—C8—C9—C4	0.4 (3)	C14—C15—C16—C17	−0.3 (4)
O1—C8—C9—C4	−179.22 (17)	C13—C12—C17—C16	1.9 (3)
C3—C4—C9—N1	−1.0 (3)	N2—C12—C17—C16	−180.0 (2)
C5—C4—C9—N1	179.5 (2)	C15—C16—C17—C12	−0.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1W^i	0.86	2.01	2.853 (2)	166
O1W—H1W1···N1	0.87 (3)	2.02 (3)	2.886 (3)	176 (3)
O1W—H2W1···O2	0.84 (3)	1.93 (3)	2.762 (2)	173 (2)
C13—H13A···O2	0.93	2.41	2.889 (3)	112

Symmetry code: (i) x−1, y, z.