Anti-inflammatory drugs. IX. Hydrated diethyl­ammonium [2-(2,6-di­chloro­phenyl­amino)­phenyl]­acetate (HDEA·D·H₂O)

In the solid-state structure of the title compound, C₄H₁₂N⁺·C₁₄H₁₀Cl₂NO₂^-·H₂O, the asymmetric unit contains one cation, one anion and a water mol­ecule. A complex network of hydrogen bonds is present. A comparison is made with the structure of the an­hydro­us salt.

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: ORTEPII (Johnson, 1976).

Diethylammonium [2-(2,6-dichlorophenylamino)phenyl]acetate hydrate

Crystal data

C4H12N^+·C14H10Cl2NO2^−·H2O	F(000) = 816
Mr = 387.29	Dx = 1.280 Mg m^−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71073 Å
a = 11.749 (1) Å	Cell parameters from 5166 reflections
b = 12.296 (1) Å	θ = 2.5–26.1°
c = 14.591 (1) Å	µ = 0.34 mm^−1
β = 107.544 (3)°	T = 293 K
V = 2009.9 (3) Å^3	Block, colourless
Z = 4	0.5 × 0.4 × 0.3 mm

Data collection

Bruker SMART 2000 CDD diffractometer	3025 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.084
Graphite monochromator	θmax = 30.1°, θmin = 1.5°
/w scans	h = −16→16
26140 measured reflections	k = −17→17
5884 independent reflections	l = −20→20

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	Weighting scheme based on measured s.u.'s w = 1/[σ^2(Fo^2) + (0.0776P)^2] where P = (Fo^2 + 2Fc^2)/3
5882 reflections	(Δ/σ)max = −0.001
250 parameters	Δρmax = 0.27 e Å^−3
58 restraints	Δρmin = −0.36 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 on F² for ALL reflections except for 2 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating _R_factor_obs 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
O3W	0.37858 (14)	0.36066 (13)	0.05331 (13)	0.0705 (4)
H1W	0.4022 (19)	0.4078 (16)	0.0898 (14)	0.065 (7)*
H2W	0.417 (2)	0.353 (2)	0.0161 (16)	0.089 (9)*
N2	0.24273 (15)	0.17862 (15)	0.06555 (12)	0.0628 (5)
H11	0.1704 (18)	0.1806 (16)	0.0167 (14)	0.069 (6)*
H12	0.2904 (19)	0.2386 (17)	0.0596 (15)	0.082 (7)*
C17	0.2162 (3)	0.1836 (3)	0.1587 (2)	0.0938 (9)
H13	0.2895	0.1738	0.2110	0.113*
H14	0.1621	0.1251	0.1618	0.113*
C18	0.1613 (3)	0.2898 (3)	0.1699 (2)	0.1103 (11)
H15	0.2157	0.3476	0.1685	0.128 (4)*
H16	0.1440	0.2911	0.2302	0.128 (4)*
H17	0.0886	0.2993	0.1183	0.128 (4)*
C15	0.3127 (2)	0.0806 (2)	0.0526 (2)	0.0920 (9)
H18	0.3871	0.0776	0.1046	0.110*
H19	0.2677	0.0153	0.0557	0.110*
C16	0.3392 (3)	0.0839 (2)	−0.0416 (2)	0.0989 (9)
H20	0.3833	0.0200	−0.0479	0.128 (4)*
H21	0.3856	0.1475	−0.0441	0.128 (4)*
H22	0.2656	0.0862	−0.0932	0.128 (4)*
Cl1	0.49102 (5)	0.30953 (5)	0.34141 (5)	0.0761 (2)
Cl2	0.75567 (4)	0.63886 (4)	0.54114 (4)	0.0665 (2)
N1	0.62960 (12)	0.51678 (13)	0.36216 (10)	0.0483 (4)
H1	0.568 (2)	0.5098 (17)	0.3138 (16)	0.075 (7)*
C1	0.73342 (14)	0.53617 (13)	0.33572 (11)	0.0426 (4)
C2	0.72775 (14)	0.61209 (13)	0.26303 (12)	0.0443 (4)
C3	0.8304 (2)	0.6286 (2)	0.23471 (14)	0.0556 (5)
H2	0.8275	0.6769	0.18501	0.067*
C4	0.9357 (2)	0.5746 (2)	0.2791 (2)	0.0656 (6)
H3	1.0029	0.5869	0.2594	0.079*
C5	0.9411 (2)	0.5033 (2)	0.3519 (2)	0.0631 (5)
H4	1.0127	0.4686	0.3828	0.076*
C6	0.8404 (2)	0.4823 (2)	0.38003 (13)	0.0542 (4)
H5	0.8442	0.4321	0.42858	0.065*
C7	0.63058 (14)	0.46594 (13)	0.44787 (12)	0.0442 (4)
C8	0.56979 (15)	0.36909 (14)	0.45045 (14)	0.0517 (4)
C9	0.5697 (2)	0.3203 (2)	0.5358 (2)	0.0675 (6)
H6	0.5281	0.2558	0.5351	0.081*
C10	0.6314 (2)	0.3678 (2)	0.6218 (2)	0.0707 (6)
H7	0.6329	0.3344	0.6794	0.085*
C11	0.6905 (2)	0.4638 (2)	0.62313 (14)	0.0623 (5)
H8	0.7318	0.4961	0.68133	0.075*
C12	0.68864 (14)	0.51274 (15)	0.53720 (12)	0.0491 (4)
C13	0.6175 (2)	0.67962 (15)	0.22115 (13)	0.0520 (4)
H9	0.6395	0.74371	0.19163	0.062*
H10	0.5884	0.70406	0.27323	0.062*
C14	0.5153 (2)	0.6220 (2)	0.14635 (12)	0.0516 (4)
O1	0.47567 (14)	0.53628 (13)	0.16993 (10)	0.0760 (5)
O2	0.47698 (12)	0.66754 (13)	0.06538 (9)	0.0699 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3W	0.0667 (10)	0.0666 (10)	0.0872 (12)	−0.0220 (8)	0.0369 (9)	−0.0128 (9)
N2	0.0496 (9)	0.0696 (11)	0.0555 (10)	−0.0203 (8)	−0.0046 (8)	0.0171 (8)
C17	0.093 (2)	0.120 (2)	0.0533 (13)	−0.051 (2)	0.0002 (12)	0.0195 (13)
C18	0.111 (2)	0.163 (3)	0.065 (2)	−0.054 (2)	0.038 (2)	−0.022 (2)
C15	0.0678 (15)	0.0607 (14)	0.120 (2)	−0.0096 (12)	−0.0130 (14)	0.0277 (13)
C16	0.081 (2)	0.078 (2)	0.132 (3)	0.0072 (14)	0.023 (2)	−0.005 (2)
Cl1	0.0594 (3)	0.0665 (3)	0.0995 (4)	−0.0112 (2)	0.0194 (3)	−0.0258 (3)
Cl2	0.0501 (3)	0.0714 (3)	0.0726 (3)	−0.0133 (2)	0.0105 (2)	−0.0135 (2)
N1	0.0286 (7)	0.0666 (10)	0.0448 (8)	−0.0012 (6)	0.0035 (6)	0.0075 (7)
C1	0.0322 (8)	0.0484 (9)	0.0447 (9)	−0.0017 (6)	0.0076 (7)	−0.0054 (7)
C2	0.0404 (8)	0.0447 (9)	0.0453 (9)	−0.0055 (7)	0.0089 (7)	−0.0086 (7)
C3	0.0561 (11)	0.0561 (11)	0.0587 (11)	−0.0151 (9)	0.0235 (9)	−0.0099 (8)
C4	0.0430 (10)	0.0776 (14)	0.0826 (15)	−0.0124 (10)	0.0286 (10)	−0.0207 (12)
C5	0.0346 (9)	0.0735 (13)	0.0773 (14)	0.0034 (9)	0.0112 (9)	−0.0123 (11)
C6	0.0397 (9)	0.0614 (11)	0.0564 (11)	0.0066 (8)	0.0068 (8)	−0.0012 (8)
C7	0.0303 (7)	0.0507 (9)	0.0492 (9)	0.0054 (7)	0.0083 (7)	0.0060 (7)
C8	0.0401 (9)	0.0460 (9)	0.0699 (12)	0.0049 (7)	0.0181 (8)	0.0015 (8)
C9	0.0609 (12)	0.0497 (11)	0.103 (2)	0.0126 (9)	0.0416 (13)	0.0193 (11)
C10	0.0716 (14)	0.0782 (15)	0.0686 (14)	0.0272 (12)	0.0305 (12)	0.0281 (12)
C11	0.0531 (11)	0.0807 (14)	0.0498 (11)	0.0192 (10)	0.0106 (9)	0.0115 (9)
C12	0.0349 (8)	0.0572 (10)	0.0520 (10)	0.0063 (7)	0.0082 (7)	0.0045 (8)
C13	0.0534 (10)	0.0483 (10)	0.0484 (10)	0.0011 (8)	0.0064 (8)	0.0015 (7)
C14	0.0393 (9)	0.0662 (12)	0.0461 (10)	0.0060 (8)	0.0080 (7)	−0.0006 (8)
O1	0.0718 (10)	0.0796 (10)	0.0581 (8)	−0.0245 (8)	−0.0082 (7)	0.0057 (7)
O2	0.0469 (7)	0.1058 (11)	0.0495 (8)	0.0030 (7)	0.0030 (6)	0.0173 (7)

Geometric parameters (Å, º)

O3W—H1W	0.78 (2)	C1—C2	1.399 (2)
O3W—H2W	0.81 (2)	C2—C3	1.403 (2)
N2—C17	1.485 (3)	C2—C13	1.505 (2)
N2—C15	1.502 (3)	C3—C4	1.381 (3)
N2—H11	0.93 (2)	C3—H2	0.93
N2—H12	0.95 (2)	C4—C5	1.363 (3)
C17—C18	1.488 (4)	C4—H3	0.93
C17—H13	0.97	C5—C6	1.389 (3)
C17—H14	0.97	C5—H4	0.93
C18—H15	0.96	C6—H5	0.93
C18—H16	0.96	C7—C8	1.395 (2)
C18—H17	0.96	C7—C12	1.400 (2)
C15—C16	1.499 (4)	C8—C9	1.382 (3)
C15—H18	0.97	C9—C10	1.377 (3)
C15—H19	0.97	C9—H6	0.93
C16—H20	0.96	C10—C11	1.367 (3)
C16—H21	0.96	C10—H7	0.93
C16—H22	0.96	C11—C12	1.385 (3)
Cl1—C8	1.743 (2)	C11—H8	0.93
Cl2—C12	1.732 (2)	C13—C14	1.531 (2)
N1—C7	1.395 (2)	C13—H9	0.97
N1—C1	1.406 (2)	C13—H10	0.97
N1—H1	0.85 (2)	C14—O1	1.242 (2)
C1—C6	1.395 (2)	C14—O2	1.261 (2)
H1W—O3W—H2W	113 (3)	C4—C3—C2	121.4 (2)
C17—N2—C15	114.9 (2)	C4—C3—H2	119.32 (12)
C17—N2—H11	107.8 (13)	C2—C3—H2	119.32 (11)
C15—N2—H11	109.5 (13)	C5—C4—C3	119.9 (2)
C17—N2—H12	110.2 (13)	C5—C4—H3	120.03 (11)
C15—N2—H12	104.6 (14)	C3—C4—H3	120.03 (12)
H11—N2—H12	109.8 (18)	C4—C5—C6	120.4 (2)
N2—C17—C18	110.7 (2)	C4—C5—H4	119.80 (11)
N2—C17—H13	109.49 (13)	C6—C5—H4	119.80 (12)
C18—C17—H13	109.49 (15)	C5—C6—C1	120.2 (2)
N2—C17—H14	109.49 (12)	C5—C6—H5	119.89 (12)
C18—C17—H14	109.49 (15)	C1—C6—H5	119.89 (11)
H13—C17—H14	108.1	C8—C7—N1	122.7 (2)
C17—C18—H15	109.47 (15)	C8—C7—C12	115.8 (2)
C17—C18—H16	109.47 (14)	N1—C7—C12	121.4 (2)
H15—C18—H16	109.5	C9—C8—C7	122.3 (2)
C17—C18—H17	109.47 (15)	C9—C8—Cl1	119.7 (2)
H15—C18—H17	109.5	C7—C8—Cl1	118.00 (14)
H16—C18—H17	109.5	C10—C9—C8	119.6 (2)
C16—C15—N2	111.5 (2)	C10—C9—H6	120.19 (13)
C16—C15—H18	109.32 (14)	C8—C9—H6	120.19 (13)
N2—C15—H18	109.32 (11)	C11—C10—C9	120.3 (2)
C16—C15—H19	109.32 (14)	C11—C10—H7	119.84 (12)
N2—C15—H19	109.32 (11)	C9—C10—H7	119.84 (13)
H18—C15—H19	108.0	C10—C11—C12	119.6 (2)
C15—C16—H20	109.47 (14)	C10—C11—H8	120.22 (12)
C15—C16—H21	109.47 (14)	C12—C11—H8	120.22 (12)
H20—C16—H21	109.5	C11—C12—C7	122.3 (2)
C15—C16—H22	109.47 (14)	C11—C12—Cl2	118.4 (2)
H20—C16—H22	109.5	C7—C12—Cl2	119.21 (13)
H21—C16—H22	109.5	C2—C13—C14	115.36 (15)
C7—N1—C1	123.27 (14)	C2—C13—H9	108.43 (10)
C7—N1—H1	118.3 (15)	C14—C13—H9	108.43 (10)
C1—N1—H1	112.5 (15)	C2—C13—H10	108.43 (10)
C6—C1—C2	119.9 (2)	C14—C13—H10	108.43 (10)
C6—C1—N1	121.8 (2)	H9—C13—H10	107.5
C2—C1—N1	118.30 (14)	O1—C14—O2	125.4 (2)
C1—C2—C3	118.1 (2)	O1—C14—C13	118.3 (2)
C1—C2—C13	120.9 (2)	O2—C14—C13	116.3 (2)
C3—C2—C13	120.8 (2)
C15—N2—C17—C18	172.5 (2)	C12—C7—C8—C9	−1.9 (2)
C17—N2—C15—C16	−178.1 (2)	N1—C7—C8—Cl1	0.6 (2)
C7—N1—C1—C6	16.8 (3)	C12—C7—C8—Cl1	177.63 (12)
C7—N1—C1—C2	−163.0 (2)	C7—C8—C9—C10	−0.1 (3)
C6—C1—C2—C3	2.2 (2)	Cl1—C8—C9—C10	−179.66 (15)
N1—C1—C2—C3	−177.96 (15)	C8—C9—C10—C11	1.4 (3)
C6—C1—C2—C13	−173.7 (2)	C9—C10—C11—C12	−0.5 (3)
N1—C1—C2—C13	6.1 (2)	C10—C11—C12—C7	−1.7 (3)
C1—C2—C3—C4	−2.2 (3)	C10—C11—C12—Cl2	175.62 (15)
C13—C2—C3—C4	173.7 (2)	C8—C7—C12—C11	2.8 (2)
C2—C3—C4—C5	0.2 (3)	N1—C7—C12—C11	179.9 (2)
C3—C4—C5—C6	1.8 (3)	C8—C7—C12—Cl2	−174.50 (12)
C4—C5—C6—C1	−1.7 (3)	N1—C7—C12—Cl2	2.5 (2)
C2—C1—C6—C5	−0.4 (3)	C1—C2—C13—C14	−79.5 (2)
N1—C1—C6—C5	179.8 (2)	C3—C2—C13—C14	104.7 (2)
C1—N1—C7—C8	−119.8 (2)	C2—C13—C14—O1	56.8 (2)
C1—N1—C7—C12	63.4 (2)	C2—C13—C14—O2	−124.2 (2)
N1—C7—C8—C9	−178.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1	0.85 (2)	2.69 (2)	2.990 (2)	102 (2)
N1—H1···O1	0.85 (2)	2.08 (2)	2.853 (2)	151 (2)
O3W—H1W···O1	0.78 (2)	2.00 (2)	2.773 (2)	172 (2)
O3W—H2W···O2^i	0.81 (2)	1.98 (2)	2.788 (2)	175 (3)
N2—H11···O2^ii	0.93 (2)	1.79 (2)	2.713 (2)	170 (2)
N2—H12···O3W	0.95 (2)	1.84 (2)	2.786 (2)	176 (2)
C5—H4···Cl2^iii	0.93	2.93	3.851 (2)	173

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