N-Phen­yl-2-(quinolin-8-yl­oxy)acetamide hemihydrate

In the title compound, C₁₇H₁₄N₂O₂·0.5H₂O, all bond lengths and angles are within normal ranges. The dihedral angle formed by the phen­yl ring with the quinoline moiety is 27.30 (9)°. The crystal packing is stabilized by inter­molecular N—H...O, C—H...O and O—H...N hydrogen bonds involv­ing the solvent water mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.049
• wR factor = 0.126
• Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
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
PLAT708_ALERT_1_C D-H..A  Calc   166.9(18), Rep      170(2), Dev..       1.72 Sigma
              N2   -H1#  -O1W     1.555   1.555   1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C17 H15 N2 O2.5
            Atom count from _chemical_formula_moiety:C17 H14.5 N2 O2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   8 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

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, 1990).

N-Phenyl-2-(quinolin-8-yloxy)acetamide hemihydrate

Crystal data

C17H14N2O2·0.5H2O	F(000) = 1208
Mr = 287.31	Dx = 1.358 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.093 (5) Å	Cell parameters from 1582 reflections
b = 12.944 (6) Å	θ = 2.4–21.7°
c = 19.584 (9) Å	µ = 0.09 mm^−1
β = 91.855 (9)°	T = 293 K
V = 2811 (2) Å^3	Block, colourless
Z = 8	0.39 × 0.17 × 0.12 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	2766 independent reflections
Radiation source: fine-focus sealed tube	1883 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 8.33 pixels mm^-1	θmax = 26.1°, θmin = 2.1°
ω scans	h = −13→10
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→15
Tmin = 0.965, Tmax = 0.989	l = −24→23
7758 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	All H-atom parameters refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.062P)^2 + 0.2335P] where P = (Fo^2 + 2Fc^2)/3
2766 reflections	(Δ/σ)max < 0.001
255 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.17 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
O1W	0.0000	1.01821 (15)	0.2500	0.0585 (5)
O1	0.13697 (12)	0.89327 (9)	0.36658 (6)	0.0527 (4)
O2	0.14888 (16)	1.06758 (12)	0.50525 (7)	0.0795 (5)
N1	0.15193 (14)	0.84257 (11)	0.23408 (8)	0.0488 (4)
N2	0.06612 (15)	1.08829 (12)	0.39837 (8)	0.0492 (4)
C1	0.15754 (19)	0.81575 (18)	0.16915 (11)	0.0567 (5)
C2	0.1724 (2)	0.71403 (19)	0.14687 (12)	0.0639 (6)
C3	0.18212 (19)	0.63771 (18)	0.19347 (12)	0.0605 (6)
C4	0.17733 (16)	0.66081 (14)	0.26357 (10)	0.0496 (5)
C5	0.19014 (19)	0.58500 (16)	0.31514 (12)	0.0615 (6)
C6	0.1862 (2)	0.61225 (17)	0.38170 (12)	0.0655 (6)
C7	0.16743 (19)	0.71525 (16)	0.40080 (11)	0.0574 (5)
C8	0.15475 (16)	0.79088 (14)	0.35243 (9)	0.0455 (5)
C9	0.16032 (15)	0.76566 (13)	0.28174 (9)	0.0431 (4)
C10	0.1429 (2)	0.92028 (16)	0.43708 (10)	0.0568 (6)
C11	0.11983 (18)	1.03325 (15)	0.44883 (10)	0.0520 (5)
C12	0.03680 (16)	1.19466 (14)	0.39950 (9)	0.0467 (5)
C13	−0.02384 (18)	1.23503 (17)	0.34282 (12)	0.0584 (6)
C14	−0.0520 (2)	1.33895 (17)	0.34006 (14)	0.0662 (6)
C15	−0.0210 (2)	1.40323 (18)	0.39349 (13)	0.0678 (6)
C16	0.0377 (3)	1.36274 (18)	0.44936 (14)	0.0790 (7)
C17	0.0676 (2)	1.25963 (17)	0.45317 (12)	0.0708 (7)
H7	0.1674 (17)	0.7301 (16)	0.4493 (11)	0.066 (6)*
H6	0.1950 (18)	0.5601 (17)	0.4164 (11)	0.076 (7)*
H1N2	0.0493 (16)	1.0584 (15)	0.3595 (10)	0.051 (6)*
H1	0.1519 (18)	0.8738 (17)	0.1374 (11)	0.066 (6)*
H13	−0.0470 (18)	1.1907 (16)	0.3057 (11)	0.066 (6)*
H2	0.176 (2)	0.7018 (18)	0.1001 (13)	0.085 (7)*
H15	−0.037 (2)	1.478 (2)	0.3896 (11)	0.086 (7)*
H3	0.1945 (19)	0.5674 (18)	0.1797 (11)	0.077 (7)*
H1W1	−0.064 (2)	0.974 (2)	0.2503 (14)	0.110 (10)*
H10B	0.224 (2)	0.9031 (18)	0.4550 (13)	0.087 (8)*
H5	0.2012 (18)	0.5108 (18)	0.3012 (10)	0.075 (6)*
H10A	0.081 (2)	0.8798 (19)	0.4615 (12)	0.086 (7)*
H14	−0.092 (2)	1.3645 (18)	0.2993 (12)	0.080 (7)*
H16	0.059 (2)	1.408 (2)	0.4856 (13)	0.102 (9)*
H17	0.107 (2)	1.2297 (18)	0.4928 (13)	0.085 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1W	0.0732 (15)	0.0369 (11)	0.0646 (13)	0.000	−0.0082 (11)	0.000
O1	0.0768 (9)	0.0396 (8)	0.0415 (8)	0.0090 (6)	−0.0024 (6)	−0.0013 (6)
O2	0.1259 (14)	0.0625 (10)	0.0487 (9)	0.0171 (9)	−0.0192 (9)	−0.0108 (7)
N1	0.0552 (10)	0.0464 (10)	0.0447 (9)	0.0025 (7)	−0.0021 (7)	0.0030 (7)
N2	0.0666 (11)	0.0401 (9)	0.0406 (9)	0.0002 (7)	−0.0017 (8)	−0.0043 (7)
C1	0.0629 (13)	0.0612 (14)	0.0458 (12)	0.0024 (10)	−0.0007 (10)	0.0019 (11)
C2	0.0729 (15)	0.0686 (16)	0.0499 (13)	0.0014 (11)	−0.0002 (11)	−0.0140 (12)
C3	0.0642 (14)	0.0509 (14)	0.0659 (15)	0.0014 (11)	−0.0032 (11)	−0.0148 (11)
C4	0.0491 (11)	0.0430 (11)	0.0565 (12)	−0.0008 (8)	−0.0010 (9)	−0.0064 (9)
C5	0.0745 (15)	0.0364 (12)	0.0733 (15)	0.0038 (10)	−0.0024 (11)	−0.0012 (11)
C6	0.0909 (17)	0.0398 (13)	0.0655 (15)	0.0045 (11)	−0.0020 (12)	0.0116 (11)
C7	0.0765 (15)	0.0460 (12)	0.0496 (12)	0.0056 (10)	−0.0015 (10)	0.0058 (10)
C8	0.0536 (11)	0.0355 (10)	0.0471 (11)	0.0038 (8)	−0.0017 (8)	0.0000 (8)
C9	0.0414 (10)	0.0388 (11)	0.0489 (11)	0.0008 (8)	−0.0008 (8)	0.0002 (8)
C10	0.0782 (16)	0.0505 (13)	0.0415 (12)	0.0068 (11)	−0.0001 (11)	−0.0009 (9)
C11	0.0680 (13)	0.0457 (12)	0.0423 (11)	0.0031 (9)	0.0014 (9)	−0.0022 (9)
C12	0.0522 (12)	0.0416 (11)	0.0464 (11)	−0.0026 (8)	0.0049 (9)	−0.0008 (8)
C13	0.0634 (14)	0.0488 (13)	0.0623 (14)	−0.0010 (10)	−0.0088 (11)	−0.0055 (10)
C14	0.0664 (15)	0.0524 (14)	0.0790 (17)	0.0042 (11)	−0.0118 (12)	0.0054 (12)
C15	0.0751 (16)	0.0419 (14)	0.0863 (18)	0.0022 (11)	−0.0003 (13)	−0.0006 (12)
C16	0.119 (2)	0.0452 (14)	0.0716 (17)	0.0017 (13)	−0.0083 (15)	−0.0136 (12)
C17	0.111 (2)	0.0483 (13)	0.0518 (13)	0.0063 (12)	−0.0120 (13)	−0.0073 (11)

Geometric parameters (Å, º)

O1W—H1W1	0.91 (2)	C6—C7	1.402 (3)
O1—C8	1.370 (2)	C6—H6	0.96 (2)
O1—C10	1.424 (2)	C7—C8	1.366 (3)
O2—C11	1.224 (2)	C7—H7	0.97 (2)
N1—C1	1.322 (3)	C8—C9	1.426 (3)
N1—C9	1.366 (2)	C10—C11	1.504 (3)
N2—C11	1.342 (2)	C10—H10B	0.99 (3)
N2—C12	1.415 (2)	C10—H10A	1.00 (2)
N2—H1N2	0.87 (2)	C12—C17	1.380 (3)
C1—C2	1.399 (3)	C12—C13	1.382 (3)
C1—H1	0.98 (2)	C13—C14	1.382 (3)
C2—C3	1.347 (3)	C13—H13	0.95 (2)
C2—H2	0.93 (2)	C14—C15	1.372 (3)
C3—C4	1.408 (3)	C14—H14	0.96 (2)
C3—H3	0.96 (2)	C15—C16	1.360 (3)
C4—C5	1.412 (3)	C15—H15	0.99 (2)
C4—C9	1.417 (3)	C16—C17	1.377 (3)
C5—C6	1.353 (3)	C16—H16	0.94 (3)
C5—H5	1.01 (2)	C17—H17	0.96 (2)
C8—O1—C10	115.56 (14)	N1—C9—C8	119.51 (16)
C1—N1—C9	117.50 (17)	C4—C9—C8	118.25 (17)
C11—N2—C12	127.00 (17)	O1—C10—C11	112.61 (16)
C11—N2—H1N2	119.1 (13)	O1—C10—H10B	107.7 (14)
C12—N2—H1N2	113.8 (13)	C11—C10—H10B	108.9 (14)
N1—C1—C2	123.9 (2)	O1—C10—H10A	108.9 (13)
N1—C1—H1	114.0 (12)	C11—C10—H10A	108.3 (14)
C2—C1—H1	122.1 (12)	H10B—C10—H10A	110.4 (19)
C3—C2—C1	119.1 (2)	O2—C11—N2	124.71 (19)
C3—C2—H2	122.4 (15)	O2—C11—C10	116.74 (18)
C1—C2—H2	118.4 (15)	N2—C11—C10	118.51 (18)
C2—C3—C4	120.0 (2)	C17—C12—C13	118.9 (2)
C2—C3—H3	121.0 (14)	C17—C12—N2	123.59 (18)
C4—C3—H3	119.0 (14)	C13—C12—N2	117.49 (17)
C3—C4—C5	122.94 (19)	C14—C13—C12	120.2 (2)
C3—C4—C9	117.24 (19)	C14—C13—H13	120.0 (12)
C5—C4—C9	119.82 (19)	C12—C13—H13	119.7 (12)
C6—C5—C4	120.2 (2)	C15—C14—C13	120.7 (2)
C6—C5—H5	121.2 (12)	C15—C14—H14	121.5 (14)
C4—C5—H5	118.7 (12)	C13—C14—H14	117.8 (14)
C5—C6—C7	121.0 (2)	C16—C15—C14	118.8 (2)
C5—C6—H6	119.5 (13)	C16—C15—H15	121.2 (13)
C7—C6—H6	119.5 (13)	C14—C15—H15	119.9 (13)
C8—C7—C6	120.6 (2)	C15—C16—C17	121.7 (2)
C8—C7—H7	122.3 (12)	C15—C16—H16	118.1 (16)
C6—C7—H7	117.1 (12)	C17—C16—H16	120.1 (16)
C7—C8—O1	124.43 (18)	C16—C17—C12	119.7 (2)
C7—C8—C9	120.16 (18)	C16—C17—H17	122.6 (15)
O1—C8—C9	115.41 (15)	C12—C17—H17	117.6 (15)
N1—C9—C4	122.23 (17)
C9—N1—C1—C2	−0.5 (3)	C7—C8—C9—N1	−177.61 (17)
N1—C1—C2—C3	−0.2 (3)	O1—C8—C9—N1	2.1 (2)
C1—C2—C3—C4	−0.1 (3)	C7—C8—C9—C4	0.9 (3)
C2—C3—C4—C5	−178.2 (2)	O1—C8—C9—C4	−179.36 (15)
C2—C3—C4—C9	0.9 (3)	C8—O1—C10—C11	−178.71 (17)
C3—C4—C5—C6	179.2 (2)	C12—N2—C11—O2	2.2 (3)
C9—C4—C5—C6	0.0 (3)	C12—N2—C11—C10	179.97 (18)
C4—C5—C6—C7	1.0 (3)	O1—C10—C11—O2	−164.36 (19)
C5—C6—C7—C8	−1.1 (3)	O1—C10—C11—N2	17.7 (3)
C6—C7—C8—O1	−179.57 (19)	C11—N2—C12—C17	4.4 (3)
C6—C7—C8—C9	0.1 (3)	C11—N2—C12—C13	−177.00 (19)
C10—O1—C8—C7	5.5 (3)	C17—C12—C13—C14	0.5 (3)
C10—O1—C8—C9	−174.21 (17)	N2—C12—C13—C14	−178.18 (19)
C1—N1—C9—C4	1.5 (3)	C12—C13—C14—C15	−0.4 (3)
C1—N1—C9—C8	179.98 (17)	C13—C14—C15—C16	−0.2 (4)
C3—C4—C9—N1	−1.7 (3)	C14—C15—C16—C17	0.7 (4)
C5—C4—C9—N1	177.51 (17)	C15—C16—C17—C12	−0.6 (4)
C3—C4—C9—C8	179.79 (17)	C13—C12—C17—C16	0.0 (3)
C5—C4—C9—C8	−1.0 (3)	N2—C12—C17—C16	178.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···N1^i	0.91 (2)	1.99 (3)	2.853 (3)	157 (2)
N2—H1N2···O1	0.87 (2)	2.35 (2)	2.722 (2)	106 (2)
N2—H1N2···O1W	0.87 (2)	2.26 (2)	3.109 (2)	170 (2)
C13—H13···O1W	0.95 (2)	2.55 (2)	3.359 (3)	143 (2)
C17—H17···O2	0.96 (2)	2.16 (2)	2.824 (3)	125 (2)

Symmetry code: (i) −x, y, −z+1/2.