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The title compound, C14H12ClNO5·H2O, is a derivative of aminobenzoic acid and forms an extensive hydrogen-bond network within the crystal.
Supporting information
CCDC reference: 170311
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
top
Crystal data top
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) Å3 | Prism, colourless |
Z = 4 | 0.64 × 0.10 × 0.03 mm |
Data collection top
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 F2 > 2σ(F2) | intensity decay: 0.0% |
Refinement top
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0774P)2 + 0.5504P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.050 | (Δ/σ)max = 0.001 |
wR(F2) = 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+0.001xFc2λ3/sin((2θ)]-1/4 |
202 parameters | Extinction coefficient: 0.0035 (6) |
Special details top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
O9—H9···O18i | 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···O20ii | 0.83 (4) | 1.96 (4) | 2.768 (4) | 163 (4) |
O20—H20B···O8iii | 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. |
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