N,N-Diphen­yl-2-(quinolin-8-yl­oxy)acetamide monohydrate

In the title compound, C₂₃H₁₈N₂O₂·H₂O, 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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](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

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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 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

Crystal data

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) Å^3	0.40 × 0.20 × 0.09 mm

Data collection

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

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0501P)^2 + 0.1798P] where P = (Fo^2 + 2Fc^2)/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

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	0.30556 (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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O1W^i	0.93	2.58	3.502 (3)	169
C23—H23A···O1W^ii	0.93	2.47	3.383 (3)	166

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