2-[(4-Carboxy­phenyl)­amino]-4-chloro­benzoic acid monohydrate

The title compound, C₁₄H₁₂ClNO₅·H₂O, is a derivative of amino­benzoic acid and forms an extensive hydrogen-bond network within the crystal.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.050
• wR factor = 0.153
• Data-to-parameter ratio = 11.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           68.85
         From the CIF: _reflns_number_total               2394
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         2534
         Completeness (_total/calc)             94.48%
          Alert C: < 95% complete


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

---

Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Bergerhoff, 1996); software used to prepare material for publication: PARST (Nardelli, 1983, 1991, 1995) and PLATON (Spek, 1990).

2-[(4-Carboxyphenyl)amino]-4-chlorobenzoic acid monohydrate

Crystal data

C14H10ClNO4·H2O	F(000) = 640
Mr = 309.70	Dx = 1.506 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54180 Å
a = 16.0658 (9) Å	Cell parameters from 41 reflections
b = 3.9597 (2) Å	θ = 4.1–40.3°
c = 21.473 (1) Å	µ = 2.69 mm^−1
β = 90.619 (6)°	T = 293 K
V = 1365.9 (1) Å^3	Prism, colourless
Z = 4	0.64 × 0.10 × 0.03 mm

Data collection

Siemens P4 four-circle diffractometer	Rint = 0.042
ω/2θ scans	θmax = 68.9°
Absorption correction: ψ scan (North et al., 1968)	h = −19→1
Tmin = 0.553, Tmax = 0.922	k = −4→1
3920 measured reflections	l = −25→25
2394 independent reflections	3 standard reflections every 100 reflections
1831 reflections with F^2 > 2σ(F^2)	intensity decay: 0.0%

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0774P)^2 + 0.5504P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.050	(Δ/σ)max = 0.001
wR(F^2) = 0.153	Δρmax = 0.30 e Å^−3
S = 1.13	Δρmin = −0.39 e Å^−3
2394 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin((2θ)]^-1/4
202 parameters	Extinction coefficient: 0.0035 (6)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.66080 (15)	0.4987 (7)	0.81896 (11)	0.0373 (6)
C2	0.66939 (15)	0.3234 (7)	0.87646 (11)	0.0356 (6)
C3	0.59732 (16)	0.2569 (7)	0.91052 (12)	0.0394 (6)
H3	0.6008	0.1342	0.9474	0.049*
C4	0.52163 (15)	0.3728 (7)	0.88946 (12)	0.0383 (6)
Cl4	0.43334 (4)	0.2796 (2)	0.93215 (4)	0.0568 (3)
C5	0.51212 (16)	0.5515 (8)	0.83445 (12)	0.0420 (7)
H5	0.4602	0.6301	0.8214	0.052*
C6	0.58247 (16)	0.6090 (8)	0.79961 (12)	0.0430 (7)
H6	0.5773	0.7248	0.7621	0.054*
C7	0.73296 (16)	0.5685 (8)	0.77906 (12)	0.0439 (7)
O8	0.80428 (12)	0.4791 (7)	0.79172 (9)	0.0623 (7)
O9	0.71551 (13)	0.7344 (7)	0.72778 (10)	0.0631 (7)
H9	0.7582	0.7621	0.7078	0.079*
N10	0.74703 (14)	0.2114 (7)	0.89529 (11)	0.0429 (6)
H10	0.783 (2)	0.242 (8)	0.8665 (16)	0.054*
C11	0.77738 (15)	0.0837 (7)	0.95153 (11)	0.0359 (6)
C12	0.85485 (15)	−0.0747 (8)	0.94937 (11)	0.0426 (7)
H12	0.8816	−0.0954	0.9114	0.053*
C13	0.89229 (16)	−0.2006 (8)	1.00221 (12)	0.0425 (7)
H13	0.9444	−0.3021	0.9997	0.053*
C14	0.85298 (15)	−0.1775 (7)	1.05952 (11)	0.0365 (6)
C15	0.77656 (15)	−0.0135 (8)	1.06195 (11)	0.0393 (6)
H15	0.7501	0.0071	1.1001	0.049*
C16	0.73899 (15)	0.1195 (7)	1.00930 (12)	0.0399 (6)
H16	0.6884	0.2323	1.0122	0.050*
C17	0.88991 (16)	−0.3221 (7)	1.11631 (12)	0.0398 (6)
O18	0.85589 (13)	−0.3379 (6)	1.16660 (9)	0.0580 (6)
O19	0.96594 (11)	−0.4439 (7)	1.10844 (9)	0.0544 (6)
H19	0.9828	−0.5274	1.1412	0.068*
O20	1.03356 (15)	−0.6853 (7)	1.21287 (11)	0.0607 (7)
H20A	1.020 (3)	−0.862 (11)	1.2311 (19)	0.076*
H20B	1.087 (3)	−0.665 (11)	1.2179 (18)	0.076*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0358 (12)	0.0396 (16)	0.0366 (11)	−0.0021 (12)	−0.0005 (9)	0.0015 (11)
C2	0.0334 (12)	0.0335 (15)	0.0399 (12)	−0.0013 (11)	−0.0005 (9)	−0.0020 (10)
C3	0.0367 (13)	0.0399 (16)	0.0416 (13)	−0.0025 (12)	0.0019 (10)	0.0036 (11)
C4	0.0342 (12)	0.0369 (16)	0.0440 (13)	−0.0031 (11)	0.0030 (10)	−0.0059 (11)
Cl4	0.0365 (4)	0.0685 (6)	0.0657 (5)	−0.0027 (3)	0.0124 (3)	0.0041 (4)
C5	0.0341 (12)	0.0437 (18)	0.0481 (14)	0.0023 (12)	−0.0044 (10)	−0.0039 (12)
C6	0.0403 (13)	0.0463 (18)	0.0422 (13)	0.0017 (13)	−0.0057 (10)	0.0048 (12)
C7	0.0418 (14)	0.0490 (18)	0.0409 (13)	−0.0001 (13)	0.0008 (10)	0.0034 (12)
O8	0.0383 (10)	0.0967 (19)	0.0520 (11)	0.0053 (12)	0.0068 (8)	0.0241 (12)
O9	0.0462 (11)	0.0957 (19)	0.0476 (11)	0.0026 (12)	0.0055 (9)	0.0264 (12)
N10	0.0316 (11)	0.0552 (16)	0.0419 (11)	0.0036 (10)	0.0022 (9)	0.0102 (11)
C11	0.0324 (12)	0.0368 (16)	0.0383 (12)	−0.0006 (11)	−0.0013 (9)	0.0028 (11)
C12	0.0363 (13)	0.0526 (19)	0.0391 (13)	0.0062 (13)	0.0069 (10)	0.0018 (12)
C13	0.0338 (13)	0.0490 (18)	0.0446 (14)	0.0084 (12)	0.0025 (10)	0.0005 (12)
C14	0.0328 (12)	0.0378 (16)	0.0388 (12)	−0.0014 (11)	−0.0009 (9)	−0.0017 (11)
C15	0.0355 (12)	0.0452 (17)	0.0374 (12)	0.0022 (12)	0.0041 (9)	−0.0045 (11)
C16	0.0319 (12)	0.0438 (17)	0.0440 (13)	0.0057 (12)	0.0012 (10)	−0.0017 (12)
C17	0.0355 (12)	0.0435 (17)	0.0404 (13)	0.0026 (12)	−0.0016 (10)	−0.0028 (11)
O18	0.0504 (11)	0.0881 (18)	0.0358 (9)	0.0135 (12)	0.0043 (8)	0.0036 (10)
O19	0.0403 (10)	0.0790 (17)	0.0440 (10)	0.0168 (11)	0.0003 (8)	0.0066 (11)
O20	0.0437 (11)	0.0763 (18)	0.0618 (13)	−0.0013 (12)	−0.0109 (10)	0.0175 (12)

Geometric parameters (Å, º)

Cl4—C4	1.737 (3)	C4—C5	1.384 (4)
O8—C7	1.227 (3)	C5—C6	1.381 (4)
O9—C7	1.310 (4)	C11—C12	1.395 (4)
O18—C17	1.217 (3)	C11—C16	1.399 (3)
O19—C17	1.326 (3)	C12—C13	1.372 (4)
O9—H9	0.820	C13—C14	1.392 (3)
O19—H19	0.820	C14—C17	1.467 (4)
O20—H20A	0.83 (4)	C14—C15	1.390 (4)
O20—H20B	0.87 (5)	C15—C16	1.380 (4)
N10—C2	1.380 (3)	C3—H3	0.930
N10—C11	1.393 (3)	C5—H5	0.930
N10—H10	0.86 (3)	C6—H6	0.930
C1—C2	1.422 (3)	C12—H12	0.930
C1—C7	1.475 (4)	C13—H13	0.930
C1—C6	1.391 (4)	C15—H15	0.930
C2—C3	1.401 (4)	C16—H16	0.930
C3—C4	1.372 (4)
C7—O9—H9	109.47	C11—C12—C13	121.3 (2)
C17—O19—H19	109.48	C12—C13—C14	120.5 (2)
H20A—O20—H20B	106 (4)	C13—C14—C15	118.2 (2)
C2—N10—C11	132.7 (2)	C15—C14—C17	120.0 (2)
C2—N10—H10	111 (2)	C13—C14—C17	121.7 (2)
C11—N10—H10	116 (2)	C14—C15—C16	121.7 (2)
C2—C1—C7	121.8 (2)	C11—C16—C15	119.7 (2)
C6—C1—C7	118.8 (2)	O18—C17—C14	125.2 (2)
C2—C1—C6	119.4 (2)	O19—C17—C14	113.6 (2)
C1—C2—C3	118.2 (2)	O18—C17—O19	121.2 (2)
N10—C2—C1	119.4 (2)	C4—C3—H3	120.0
N10—C2—C3	122.4 (2)	C2—C3—H3	120.0
C2—C3—C4	120.0 (2)	C4—C5—H5	121.2
Cl4—C4—C3	118.8 (2)	C6—C5—H5	121.2
Cl4—C4—C5	118.41 (19)	C5—C6—H6	119.0
C3—C4—C5	122.8 (2)	C1—C6—H6	119.0
C4—C5—C6	117.6 (2)	C11—C12—H12	119.4
C1—C6—C5	122.0 (2)	C13—C12—H12	119.4
O8—C7—O9	121.5 (2)	C14—C13—H13	119.7
O8—C7—C1	123.7 (2)	C12—C13—H13	119.7
O9—C7—C1	114.8 (2)	C14—C15—H15	119.1
C12—C11—C16	118.5 (2)	C16—C15—H15	119.1
N10—C11—C12	116.0 (2)	C11—C16—H16	120.2
N10—C11—C16	125.4 (2)	C15—C16—H16	120.2
C2—N10—C11—C12	166.0 (3)	Cl4—C4—C5—C6	−176.9 (2)
C11—N10—C2—C1	168.4 (3)	C3—C4—C5—C6	0.8 (4)
C11—N10—C2—C3	−14.7 (5)	C4—C5—C6—C1	−1.2 (4)
C2—N10—C11—C16	−17.9 (5)	N10—C11—C16—C15	−178.6 (3)
C6—C1—C7—O8	−179.3 (3)	C12—C11—C16—C15	−2.6 (4)
C6—C1—C2—C3	2.4 (4)	N10—C11—C12—C13	177.9 (3)
C6—C1—C2—N10	179.4 (3)	C16—C11—C12—C13	1.5 (4)
C6—C1—C7—O9	0.3 (4)	C11—C12—C13—C14	1.0 (5)
C2—C1—C7—O9	−179.5 (3)	C12—C13—C14—C15	−2.2 (4)
C7—C1—C2—N10	−0.8 (4)	C12—C13—C14—C17	177.4 (3)
C2—C1—C7—O8	0.9 (4)	C15—C14—C17—O18	6.6 (4)
C2—C1—C6—C5	−0.4 (4)	C13—C14—C15—C16	1.1 (4)
C7—C1—C2—C3	−177.8 (3)	C13—C14—C17—O19	6.0 (4)
C7—C1—C6—C5	179.7 (3)	C17—C14—C15—C16	−178.6 (3)
N10—C2—C3—C4	−179.6 (3)	C15—C14—C17—O19	−174.3 (3)
C1—C2—C3—C4	−2.8 (4)	C13—C14—C17—O18	−173.1 (3)
C2—C3—C4—C5	1.2 (4)	C14—C15—C16—C11	1.4 (5)
C2—C3—C4—Cl4	178.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O9—H9···O18^i	0.82	1.83	2.654 (3)	177
N10—H10···O8	0.86 (3)	1.89 (3)	2.638 (3)	144 (3)
O19—H19···O20	0.82	1.84	2.659 (3)	172
O20—H20A···O20^ii	0.83 (4)	1.96 (4)	2.768 (4)	163 (4)
O20—H20B···O8^iii	0.87 (5)	1.91 (5)	2.733 (3)	158 (4)

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+2, y−1/2, −z+5/2; (iii) −x+2, −y, −z+2.