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

organic papers

o3630

18H16N2O3H2O doi:10.1107/S1600536805031557 Acta Cryst.(2005). E61, o3630–o3631

Acta Crystallographica Section E

Structure Reports

Online

ISSN 1600-5368

N

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

Yong-Hong Wen, Mao-Jie Li, Shu-Sheng Zhang* and Xue-Mei Li

College of Chemistry and Molecular

Engineering, Qingdao University of Science and Technology, 266042 Qingdao, Shandong, People’s Republic of China

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study

T= 293 K

Mean(C–C) = 0.003 A˚

Rfactor = 0.032

wRfactor = 0.083 Data-to-parameter ratio = 8.4

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2005 International Union of Crystallography

Printed in Great Britain – all rights reserved

In the title compound, C18H16N2O3H2O, 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–interactions.

Comment

Recently, we have reported the structure of an amide-type acyclic compound with 8-hydroxyquinolinate as the skeleton, namelyN-phenyl-2-(quinolin-8-yloxy)acetamide hemihydrate, (II) (Liet al., 2005). We have synthesized and carried out the structure determination of the title compound, (I), reported here.

All bond lengths and angles in (I) (Table 1) are within normal ranges (Allenet al., 1987) and comparable with those in the related compound (II). The dihedral angle formed by the benzene ring with the quinoline moiety is 67.06 (7). There is one intramolecular hydrogen bond,viz. C13—H13A O2, forming a six-membered ring. In the crystal structure, mol-ecules are linked into chains along theaaxis by intermolecular N2—H2A O1Wi, O1W—H2W1 O2ii and O1W— H1W1 N1iihydrogen bonds (Table 2 and Fig. 2) involving the solvent water molecule. The packing is further stabilized by –interactions involving the benzene rings (Cg2 is the centroid of the C12–C17 benzene ring):Cg3 Cg3(1

2+x, 1 2 y,z) = 3.737 A˚ .

Experimental

To a solution of 8-hydroxyquinoline (2.9 g, 20 mmol) in acetone (40 ml) were added 2-chloro-N-(4-methoxyphenyl)acetamide (3.99 g, 20 mmol), K2CO3(3.04 g, 22 mmol) and KI (0.5 g), and the resulting

mixture was stirred at 333 K for 5 h. After cooling to room temperature, the mixture was washed three times with water and then filtered. The title compound was obtained after drying the yellow powder at room temperature for 48 h. Yellow single crystals suitable for X-ray diffraction study were obtained by slow evaporation of a petroleum ether–ethyl acetate (1:3v/v) solution over a period of 6 d.

Crystal data

C18H16N2O3H2O

Mr= 326.34

Orthorhombic,P212121

a= 6.8814 (13) A˚ b= 11.627 (2) A˚ c= 20.468 (4) A˚ V= 1637.6 (5) A˚3

Z= 4

Dx= 1.324 Mg m

3

MoKradiation Cell parameters from 4023

reflections = 2.6–25.8

= 0.10 mm1

T= 293 (2) K Plate, yellow

0.420.420.12 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer !scans

Absorption correction: multi-scan (SADABS; Sheldrick, 1996) Tmin= 0.961,Tmax= 0.989

9310 measured reflections

1901 independent reflections 1737 reflections withI> 2(I) Rint= 0.018

max= 26.1

h=8!8 k=13!14 l=25!24

Refinement

Refinement onF2

R[F2> 2(F2)] = 0.032 wR(F2_{) = 0.084}

S= 1.12 1901 reflections 225 parameters

H atoms treated by a mixture of independent and constrained refinement

w= 1/[2_(F

o2) + (0.0392P)2

+ 0.1826P]

whereP= (Fo2+ 2Fc2)/3

(/)max< 0.001

max= 0.13 e A˚

3

min=0.14 e A˚

3

Table 1

Selected bond lengths (A˚ ).

O1—C8 1.371 (2) O1—C10 1.418 (2) O2—C11 1.223 (2)

N2—C11 1.340 (2) N2—C12 1.426 (2)

Table 2

Hydrogen-bond geometry (A˚ ,_).

D—H A D—H H A D A D—H A

N2—H2A O1Wi 0.86 2.01 2.853 (2) 166 O1W—H1W1 N1ii

0.87 (3) 2.02 (3) 2.886 (3) 176 (3) O1W—H2W1 O2ii

0.84 (3) 1.93 (3) 2.762 (2) 173 (2) C13—H13A O2ii

0.93 2.41 2.889 (3) 112

Symmetry code: (i)x1;y;z; (ii)x;y;z.

All H atoms were located in difference Fourier maps and all except water H atoms, which were refined freely, were constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 A˚ , and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms. The

Friedel reflections were merged before the final refinement because of the absence of any significant anomalous scattering effects.

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) andPLATON(Spek, 2003).

This project was supported by the Program for New Century Excellent Talents in Universities (No. NCET-04–

0649), and by the Project of Educational Administration of Shandong Province (No. J04B12).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987).J. Chem. Soc. Perkin Trans. 2, S1–19.

Li, X.-M., Wen, Y.-H., Li, M.-J. & Zhang, S.-S. (2005).Acta Cryst.E61, o2389– o2390.

Nardelli, M. (1995).J. Appl. Cryst.28, 659.

Sheldrick, G. M. (1996).SADABS. University of Go¨ttingen, Germany. Sheldrick, G. M. (1997).SHELXTL. Version 5.1. Bruker AXS Inc., Madison,

Wisconsin, USA.

Siemens (1996).SMARTandSAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Spek, A. L. (2003).J. Appl. Cryst.36, 7–13.

Figure 1

The structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.

Figure 2

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sup-1 Acta Cryst. (2005). E61, o3630–o3631

supporting information

Acta Cryst. (2005). E61, o3630–o3631 [https://doi.org/10.1107/S1600536805031557]

N

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

Yong-Hong Wen, Mao-Jie Li, Shu-Sheng Zhang and Xue-Mei Li

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

Crystal data

C18H16N2O3·H2O

Mr = 326.34

Orthorhombic, P212121

a = 6.8814 (13) Å

b = 11.627 (2) Å

c = 20.468 (4) Å

V = 1637.6 (5) Å3

Z = 4

F(000) = 688

Dx = 1.324 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 4023 reflections

θ = 2.6–25.8°

µ = 0.10 mm−1

T = 293 K Block, yellow

0.42 × 0.42 × 0.12 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

Detector resolution: 8.33 pixels mm-1

ω scans

Absorption correction: empirical (using intensity measurements)

(SADABS; Sheldrick, 1996)

Tmin = 0.961, Tmax = 0.989 9310 measured reflections 1901 independent reflections 1737 reflections with I > 2σ(I)

Rint = 0.018

θmax = 26.1°, θmin = 2.0°

h = −8→8

k = −13→14

l = −25→24

Refinement

Refinement on F2 Least-squares matrix: full

R[F2 _{> 2σ(F}2_{)] = 0.032}

wR(F2_{) = 0.084}

S = 1.12 1901 reflections 225 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H atoms treated by a mixture of independent and constrained refinement

w = 1/[σ2_(F

o2) + (0.0392P)2 + 0.1826P] where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001 Δρmax = 0.13 e Å−3 Δρmin = −0.14 e Å−3

Special details

Refinement. Refinement of F2 _{against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F}2_, conventional R-factors R are based on F, with F set to zero for negative F2_{. The threshold expression of F}2 _{> σ(F}2_{) 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₎

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*

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sup-3 Acta Cryst. (2005). E61, o3630–o3631

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 (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

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—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)

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sup-5 Acta Cryst. (2005). E61, o3630–o3631

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···O1Wi _{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