N-(3-Methoxy­phen­yl)-2-(quinolin-8-yl­oxy)acetamide monohydrate

In the title compound, C₁₈H₁₆N₂O₃·H₂O, the organic mol­ecules and water molecules are linked by inter­molecular N—H...O, O—H...O and O—H...N hydrogen bonds. The structure is also stabilized by C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.047
• wR factor = 0.097
• Data-to-parameter ratio = 7.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.62
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.847(10) ......       3.00 su-Ra
              O1W  -H1W     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.86(3), Rep   0.857(10) ......       3.00 su-Ra
              O1W  -H2W     1.555   1.555

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           26.06
           From the CIF: _reflns_number_total               1706
           Count of symmetry unique reflns         1721
           Completeness (_total/calc)             99.13%
           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
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
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   5 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
   2 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

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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-(3-Methoxyphenyl)-2-(quinolin-8-yloxy)acetamide monohydrate

Crystal data

C18H16N2O3·H2O	F(000) = 344
Mr = 326.34	Dx = 1.355 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1062 reflections
a = 8.1881 (11) Å	θ = 2.5–22.9°
b = 7.0491 (10) Å	µ = 0.10 mm^−1
c = 14.094 (2) Å	T = 293 K
β = 100.553 (2)°	Block, colourless
V = 799.75 (19) Å^3	0.26 × 0.16 × 0.12 mm
Z = 2

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	1706 independent reflections
Radiation source: fine-focus sealed tube	1288 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 8.33 pixels mm^-1	θmax = 26.1°, θmin = 1.5°
ω scans	h = −9→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −8→8
Tmin = 0.975, Tmax = 0.989	l = −13→17
4571 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)] = 0.047	Hydrogen site location: difference Fourier map
wR(F^2) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0469P)^2 + 0.0065P] where P = (Fo^2 + 2Fc^2)/3
1706 reflections	(Δ/σ)max < 0.001
224 parameters	Δρmax = 0.14 e Å^−3
3 restraints	Δρmin = −0.15 e Å^−3
65 constraints

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
O1W	0.7750 (4)	0.6915 (4)	0.1053 (2)	0.0648 (7)
H1W	0.730 (5)	0.795 (4)	0.117 (3)	0.090 (11)*
H2W	0.803 (5)	0.700 (7)	0.0497 (15)	0.090 (11)*
O1	0.7023 (3)	0.0511 (3)	0.98167 (15)	0.0511 (6)
O2	0.6257 (3)	0.0294 (3)	1.15802 (18)	0.0618 (7)
O3	0.8185 (3)	0.7170 (4)	1.46917 (16)	0.0692 (8)
N1	0.8503 (3)	−0.2497 (4)	0.9194 (2)	0.0478 (7)
N2	0.6730 (3)	0.3448 (4)	1.17961 (18)	0.0442 (7)
H2B	0.6906	0.4467	1.1495	0.053*
C1	0.7967 (4)	−0.1079 (4)	0.8548 (2)	0.0417 (8)
C2	0.9218 (4)	−0.3979 (5)	0.8872 (3)	0.0548 (9)
H2A	0.9585	−0.4947	0.9308	0.066*
C3	0.9462 (4)	−0.4197 (6)	0.7927 (3)	0.0616 (10)
H3A	0.9967	−0.5282	0.7740	0.074*
C4	0.8949 (4)	−0.2792 (5)	0.7286 (3)	0.0590 (10)
H4A	0.9108	−0.2908	0.6652	0.071*
C5	0.8178 (4)	−0.1161 (5)	0.7570 (2)	0.0468 (8)
C6	0.7573 (4)	0.0331 (6)	0.6943 (2)	0.0600 (10)
H6A	0.7688	0.0279	0.6299	0.072*
C7	0.6826 (5)	0.1840 (6)	0.7269 (3)	0.0617 (10)
H7A	0.6437	0.2818	0.6844	0.074*
C8	0.6620 (4)	0.1972 (5)	0.8236 (2)	0.0510 (8)
H8A	0.6110	0.3029	0.8447	0.061*
C9	0.7177 (4)	0.0535 (5)	0.8861 (2)	0.0439 (8)
C10	0.6507 (4)	0.2206 (4)	1.0207 (2)	0.0492 (8)
H10A	0.5404	0.2554	0.9874	0.059*
H10B	0.7265	0.3230	1.0133	0.059*
C11	0.6495 (4)	0.1864 (5)	1.1264 (2)	0.0444 (8)
C12	0.6722 (4)	0.3646 (4)	1.2802 (2)	0.0417 (7)
C13	0.7477 (4)	0.5267 (5)	1.3232 (2)	0.0443 (8)
H13A	0.7973	0.6127	1.2871	0.053*
C14	0.7490 (4)	0.5601 (6)	1.4199 (2)	0.0498 (8)
C15	0.6782 (5)	0.4307 (6)	1.4737 (3)	0.0600 (10)
H15A	0.6805	0.4517	1.5390	0.072*
C16	0.6051 (5)	0.2718 (6)	1.4302 (3)	0.0665 (11)
H16A	0.5578	0.1849	1.4668	0.080*
C17	0.5990 (4)	0.2359 (5)	1.3330 (3)	0.0550 (9)
H17A	0.5469	0.1278	1.3042	0.066*
C18	0.8902 (5)	0.8547 (6)	1.4173 (3)	0.0768 (12)
H18A	0.9339	0.9562	1.4598	0.115*
H18B	0.8072	0.9036	1.3661	0.115*
H18C	0.9784	0.7982	1.3906	0.115*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1W	0.102 (2)	0.0427 (14)	0.0535 (17)	0.0023 (15)	0.0238 (15)	0.0062 (14)
O1	0.0763 (15)	0.0368 (12)	0.0407 (13)	0.0077 (12)	0.0118 (11)	0.0002 (12)
O2	0.0921 (18)	0.0382 (14)	0.0594 (15)	−0.0093 (13)	0.0253 (13)	−0.0026 (13)
O3	0.0960 (19)	0.0695 (19)	0.0401 (14)	−0.0120 (16)	0.0075 (13)	−0.0117 (14)
N1	0.0528 (17)	0.0423 (17)	0.0472 (16)	0.0039 (13)	0.0060 (14)	0.0014 (14)
N2	0.0610 (17)	0.0317 (15)	0.0393 (16)	0.0008 (13)	0.0077 (13)	0.0011 (13)
C1	0.0421 (17)	0.0413 (19)	0.0396 (18)	−0.0071 (15)	0.0018 (14)	−0.0046 (16)
C2	0.055 (2)	0.047 (2)	0.061 (2)	0.0056 (17)	0.0052 (18)	−0.0026 (19)
C3	0.057 (2)	0.064 (3)	0.065 (3)	0.003 (2)	0.0146 (19)	−0.017 (2)
C4	0.060 (2)	0.067 (3)	0.051 (2)	−0.009 (2)	0.0149 (19)	−0.017 (2)
C5	0.0466 (19)	0.050 (2)	0.0427 (19)	−0.0105 (16)	0.0043 (15)	−0.0054 (18)
C6	0.073 (2)	0.071 (3)	0.038 (2)	−0.008 (2)	0.0123 (18)	0.002 (2)
C7	0.079 (3)	0.055 (2)	0.049 (2)	−0.003 (2)	0.008 (2)	0.013 (2)
C8	0.063 (2)	0.042 (2)	0.046 (2)	−0.0011 (19)	0.0046 (16)	0.0054 (18)
C9	0.0508 (18)	0.0414 (18)	0.0380 (19)	−0.0064 (17)	0.0045 (15)	−0.0027 (17)
C10	0.066 (2)	0.036 (2)	0.0433 (19)	0.0038 (17)	0.0042 (16)	−0.0042 (17)
C11	0.0476 (19)	0.0382 (18)	0.047 (2)	0.0017 (16)	0.0079 (15)	0.0014 (18)
C12	0.0460 (18)	0.0397 (18)	0.0396 (18)	0.0070 (15)	0.0081 (14)	0.0035 (16)
C13	0.0523 (19)	0.0414 (18)	0.0391 (19)	0.0019 (16)	0.0082 (14)	0.0049 (16)
C14	0.0548 (19)	0.053 (2)	0.040 (2)	0.0062 (18)	0.0047 (16)	0.0014 (18)
C15	0.069 (2)	0.075 (3)	0.037 (2)	0.005 (2)	0.0121 (18)	0.006 (2)
C16	0.082 (3)	0.071 (3)	0.052 (2)	−0.003 (2)	0.026 (2)	0.014 (2)
C17	0.061 (2)	0.046 (2)	0.060 (2)	−0.0009 (17)	0.0145 (18)	0.0051 (18)
C18	0.092 (3)	0.065 (3)	0.070 (3)	−0.011 (2)	0.006 (2)	−0.009 (2)

Geometric parameters (Å, º)

O1W—H1W	0.847 (10)	C6—H6A	0.9300
O1W—H2W	0.857 (10)	C7—C8	1.406 (5)
O1—C9	1.376 (4)	C7—H7A	0.9300
O1—C10	1.412 (4)	C8—C9	1.365 (5)
O2—C11	1.222 (4)	C8—H8A	0.9300
O3—C14	1.373 (4)	C10—C11	1.511 (4)
O3—C18	1.407 (5)	C10—H10A	0.9700
N1—C2	1.318 (4)	C10—H10B	0.9700
N1—C1	1.369 (4)	C12—C17	1.379 (4)
N2—C11	1.338 (4)	C12—C13	1.385 (4)
N2—C12	1.425 (4)	C13—C14	1.382 (4)
N2—H2B	0.8600	C13—H13A	0.9300
C1—C9	1.418 (4)	C14—C15	1.379 (5)
C1—C5	1.421 (4)	C15—C16	1.361 (6)
C2—C3	1.391 (5)	C15—H15A	0.9300
C2—H2A	0.9300	C16—C17	1.385 (5)
C3—C4	1.355 (5)	C16—H16A	0.9300
C3—H3A	0.9300	C17—H17A	0.9300
C4—C5	1.404 (5)	C18—H18A	0.9600
C4—H4A	0.9300	C18—H18B	0.9600
C5—C6	1.405 (5)	C18—H18C	0.9600
C6—C7	1.349 (5)
H1W—O1W—H2W	108 (4)	O1—C10—C11	107.8 (3)
C9—O1—C10	117.3 (2)	O1—C10—H10A	110.1
C14—O3—C18	117.8 (3)	C11—C10—H10A	110.1
C2—N1—C1	117.3 (3)	O1—C10—H10B	110.1
C11—N2—C12	127.8 (3)	C11—C10—H10B	110.1
C11—N2—H2B	116.1	H10A—C10—H10B	108.5
C12—N2—H2B	116.1	O2—C11—N2	124.6 (3)
N1—C1—C9	119.2 (3)	O2—C11—C10	122.2 (3)
N1—C1—C5	122.3 (3)	N2—C11—C10	113.2 (3)
C9—C1—C5	118.5 (3)	C17—C12—C13	120.6 (3)
N1—C2—C3	124.6 (4)	C17—C12—N2	123.7 (3)
N1—C2—H2A	117.7	C13—C12—N2	115.7 (3)
C3—C2—H2A	117.7	C14—C13—C12	119.6 (3)
C4—C3—C2	118.4 (4)	C14—C13—H13A	120.2
C4—C3—H3A	120.8	C12—C13—H13A	120.2
C2—C3—H3A	120.8	O3—C14—C15	115.6 (3)
C3—C4—C5	120.6 (3)	O3—C14—C13	124.3 (3)
C3—C4—H4A	119.7	C15—C14—C13	120.1 (4)
C5—C4—H4A	119.7	C16—C15—C14	119.4 (3)
C4—C5—C6	124.0 (3)	C16—C15—H15A	120.3
C4—C5—C1	116.8 (3)	C14—C15—H15A	120.3
C6—C5—C1	119.2 (3)	C15—C16—C17	121.9 (4)
C7—C6—C5	120.3 (3)	C15—C16—H16A	119.1
C7—C6—H6A	119.8	C17—C16—H16A	119.1
C5—C6—H6A	119.8	C12—C17—C16	118.3 (4)
C6—C7—C8	121.7 (4)	C12—C17—H17A	120.8
C6—C7—H7A	119.2	C16—C17—H17A	120.8
C8—C7—H7A	119.2	O3—C18—H18A	109.5
C9—C8—C7	119.4 (4)	O3—C18—H18B	109.5
C9—C8—H8A	120.3	H18A—C18—H18B	109.5
C7—C8—H8A	120.3	O3—C18—H18C	109.5
C8—C9—O1	124.1 (3)	H18A—C18—H18C	109.5
C8—C9—C1	120.8 (3)	H18B—C18—H18C	109.5
O1—C9—C1	115.1 (3)
C2—N1—C1—C9	179.4 (3)	N1—C1—C9—O1	0.1 (4)
C2—N1—C1—C5	−0.7 (4)	C5—C1—C9—O1	−179.8 (3)
C1—N1—C2—C3	0.0 (5)	C9—O1—C10—C11	−177.8 (3)
N1—C2—C3—C4	0.6 (5)	C12—N2—C11—O2	−1.3 (5)
C2—C3—C4—C5	−0.4 (5)	C12—N2—C11—C10	177.2 (3)
C3—C4—C5—C6	−178.3 (3)	O1—C10—C11—O2	−28.3 (4)
C3—C4—C5—C1	−0.3 (5)	O1—C10—C11—N2	153.1 (3)
N1—C1—C5—C4	0.9 (4)	C11—N2—C12—C17	−20.2 (5)
C9—C1—C5—C4	−179.3 (3)	C11—N2—C12—C13	161.2 (3)
N1—C1—C5—C6	178.9 (3)	C17—C12—C13—C14	−0.3 (4)
C9—C1—C5—C6	−1.2 (4)	N2—C12—C13—C14	178.3 (3)
C4—C5—C6—C7	179.1 (3)	C18—O3—C14—C15	−179.1 (3)
C1—C5—C6—C7	1.1 (5)	C18—O3—C14—C13	1.3 (5)
C5—C6—C7—C8	−0.3 (5)	C12—C13—C14—O3	−179.2 (3)
C6—C7—C8—C9	−0.5 (5)	C12—C13—C14—C15	1.3 (5)
C7—C8—C9—O1	−179.3 (3)	O3—C14—C15—C16	179.3 (3)
C7—C8—C9—C1	0.4 (5)	C13—C14—C15—C16	−1.1 (5)
C10—O1—C9—C8	−10.7 (4)	C14—C15—C16—C17	−0.1 (6)
C10—O1—C9—C1	169.6 (3)	C13—C12—C17—C16	−0.9 (5)
N1—C1—C9—C8	−179.7 (3)	N2—C12—C17—C16	−179.4 (3)
C5—C1—C9—C8	0.4 (4)	C15—C16—C17—C12	1.1 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2^i	0.85 (3)	1.99 (3)	2.838 (4)	174 (4)
N2—H2B···O1W^ii	0.86	2.00	2.844 (4)	167
O1W—H2W···N1^i	0.86 (3)	1.98 (3)	2.830 (4)	173 (4)
C8—H8A···O2^iii	0.93	2.50	3.365 (4)	154
C13—H13A···O1W^ii	0.93	2.59	3.329 (4)	136
C17—H17A···O2	0.93	2.37	2.906 (5)	116

Symmetry codes: (i) x, y+1, z−1; (ii) x, y, z+1; (iii) −x+1, y+1/2, −z+2.