The title compound, C14H13NO3, is a derivative of 2-aminobenzoic acid. The molecules form dimers via hydrogen bonding of carboxylic acid groups. The title structure has four molecules in the asymmetric unit, which is quite unusual.
Supporting information
CCDC reference: 170780
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.011 Å
- R factor = 0.053
- wR factor = 0.155
- Data-to-parameter ratio = 7.5
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
General Notes
REFLT_03
From the CIF: _diffrn_reflns_theta_max 69.13
From the CIF: _reflns_number_total 4933
Count of symmetry unique reflns 4563
Completeness (_total/calc) 108.11%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 370
Fraction of Friedel pairs measured 0.081
Are heavy atom types Z>Si present no
WARNING: CuKa measured Friedel data can be used to
determine absolute structure in a light-atom
study only if the Friedel fraction is large.
The synthesis was carried out by the reaction of 2-chlorobenzoic acid with
4-methoxyaniline, in the presence of K2CO3, DMF and Cu powder. In the
recrystallization from ethanol–water (1:1), colourless prisms of the title
compound were obtained.
The H-atom positions of the imino group and those of the water molecule were
obtained from de differenece Fourier synthesis and the coordinates allowed to
refine. The OH groups were found from a circular difference Fourier synthesis
and allowed to refine as a `rotating group'. The remaining H atoms were
calculated geometrically and included in the refinement, but were restrained
to ride on their parent atoms. The isotropic displacement parameters of the H
atoms were fixed to 1.2Ueq of their parent atoms.
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, 1991) and PLATON (Spek, 1990).
2-(4-methoxyphenyl)aminobenzoic acid
top
Crystal data top
C14H13NO3 | F(000) = 1024 |
Mr = 243.25 | Dx = 1.321 Mg m−3 |
Monoclinic, Pc | Cu Kα radiation, λ = 1.54180 Å |
a = 12.6506 (6) Å | Cell parameters from 39 reflections |
b = 10.1894 (5) Å | θ = 10.6–27.7° |
c = 19.8565 (12) Å | µ = 0.77 mm−1 |
β = 107.160 (5)° | T = 293 K |
V = 2445.6 (2) Å3 | Plate, black |
Z = 8 | 0.50 × 0.22 × 0.08 mm |
Data collection top
Siemens P4 four-circle diffractometer | Rint = 0.053 |
ω/2θ scans | θmax = 69.1° |
Absorption correction: ψ scan (North et al., 1968) | h = −15→1 |
Tmin = 0.699, Tmax = 0.940 | k = −1→12 |
5863 measured reflections | l = −23→24 |
4933 independent reflections | 3 standard reflections every 100 reflections |
3152 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) + (0.0808P)2 + 0.0125P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.053 | (Δ/σ)max = 0.001 |
wR(F2) = 0.155 | Δρmax = 0.20 e Å−3 |
S = 1.05 | Δρmin = −0.18 e Å−3 |
4933 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin((2θ)]-1/4 |
658 parameters | Extinction coefficient: 0.0010 (2) |
Crystal data top
C14H13NO3 | V = 2445.6 (2) Å3 |
Mr = 243.25 | Z = 8 |
Monoclinic, Pc | Cu Kα radiation |
a = 12.6506 (6) Å | µ = 0.77 mm−1 |
b = 10.1894 (5) Å | T = 293 K |
c = 19.8565 (12) Å | 0.50 × 0.22 × 0.08 mm |
β = 107.160 (5)° | |
Data collection top
Siemens P4 four-circle diffractometer | 3152 reflections with F2 > 2σ(F2) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.053 |
Tmin = 0.699, Tmax = 0.940 | 3 standard reflections every 100 reflections |
5863 measured reflections | intensity decay: 0.0% |
4933 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.053 | 658 parameters |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.20 e Å−3 |
4933 reflections | Δρmin = −0.18 e Å−3 |
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 | |
O8 | −0.1675 (5) | −0.2522 (6) | 0.9062 (3) | 0.0576 (19) | |
O9 | 0.0010 (5) | −0.2921 (5) | 0.8998 (3) | 0.0520 (17) | |
O17 | 0.5920 (5) | 0.0251 (6) | 0.9857 (3) | 0.068 (2) | |
N10 | 0.1637 (5) | −0.1329 (6) | 0.9690 (4) | 0.055 (2) | |
C1 | −0.0252 (6) | −0.1262 (6) | 0.9783 (3) | 0.038 (2) | |
C2 | 0.0869 (7) | −0.0779 (7) | 0.9988 (4) | 0.043 (2) | |
C3 | 0.1133 (7) | 0.0269 (7) | 1.0487 (4) | 0.045 (2) | |
C4 | 0.0360 (7) | 0.0802 (7) | 1.0740 (4) | 0.053 (3) | |
C5 | −0.0707 (8) | 0.0335 (8) | 1.0555 (4) | 0.055 (3) | |
C6 | −0.1007 (7) | −0.0680 (7) | 1.0090 (4) | 0.049 (3) | |
C7 | −0.0599 (7) | −0.2298 (7) | 0.9260 (4) | 0.042 (2) | |
C11 | 0.2732 (7) | −0.0905 (7) | 0.9774 (4) | 0.047 (3) | |
C12 | 0.3026 (6) | −0.0812 (6) | 0.9131 (3) | 0.052 (2) | |
C13 | 0.4084 (6) | −0.0458 (7) | 0.9151 (3) | 0.056 (2) | |
C14 | 0.4839 (6) | −0.0146 (7) | 0.9789 (4) | 0.045 (2) | |
C15 | 0.4543 (5) | −0.0226 (6) | 1.0394 (3) | 0.046 (2) | |
C16 | 0.3493 (6) | −0.0596 (6) | 1.0380 (3) | 0.0447 (19) | |
C18 | 0.6217 (7) | 0.0472 (9) | 0.9230 (5) | 0.089 (3) | |
O28 | 0.9406 (5) | 0.0036 (5) | 1.3105 (3) | 0.0527 (17) | |
O29 | 0.7693 (4) | −0.0515 (5) | 1.3102 (3) | 0.0496 (17) | |
O37 | 0.1828 (5) | 0.2495 (6) | 1.2364 (4) | 0.069 (2) | |
N30 | 0.6029 (6) | 0.0958 (6) | 1.2331 (3) | 0.055 (2) | |
C21 | 0.7921 (7) | 0.1228 (7) | 1.2360 (4) | 0.043 (2) | |
C22 | 0.6814 (7) | 0.1610 (7) | 1.2109 (4) | 0.043 (2) | |
C23 | 0.6510 (7) | 0.2591 (7) | 1.1603 (5) | 0.054 (3) | |
C24 | 0.7303 (8) | 0.3202 (8) | 1.1355 (4) | 0.061 (3) | |
C25 | 0.8408 (8) | 0.2856 (8) | 1.1617 (5) | 0.059 (3) | |
C26 | 0.8696 (7) | 0.1887 (7) | 1.2117 (4) | 0.049 (3) | |
C27 | 0.8321 (7) | 0.0188 (7) | 1.2881 (4) | 0.041 (3) | |
C31 | 0.4971 (6) | 0.1431 (7) | 1.2336 (4) | 0.046 (2) | |
C32 | 0.4750 (6) | 0.2707 (6) | 1.2418 (4) | 0.058 (3) | |
C33 | 0.3698 (7) | 0.3120 (7) | 1.2419 (4) | 0.067 (3) | |
C34 | 0.2861 (8) | 0.2213 (8) | 1.2347 (5) | 0.054 (3) | |
C35 | 0.3080 (6) | 0.0912 (6) | 1.2248 (3) | 0.055 (2) | |
C36 | 0.4113 (6) | 0.0500 (6) | 1.2235 (3) | 0.048 (2) | |
C38 | 0.1600 (7) | 0.3800 (8) | 1.2525 (5) | 0.087 (4) | |
O48 | −0.1754 (4) | 0.2507 (5) | 0.8959 (3) | 0.0532 (17) | |
O49 | −0.0049 (5) | 0.1977 (5) | 0.8979 (3) | 0.0514 (17) | |
O57 | 0.5815 (5) | 0.5101 (6) | 0.9763 (4) | 0.067 (2) | |
N50 | 0.1610 (6) | 0.3467 (6) | 0.9746 (4) | 0.060 (3) | |
C41 | −0.0328 (6) | 0.3711 (7) | 0.9723 (4) | 0.039 (2) | |
C42 | 0.0818 (7) | 0.4063 (7) | 0.9983 (4) | 0.043 (3) | |
C43 | 0.1081 (8) | 0.5060 (7) | 1.0510 (4) | 0.052 (3) | |
C44 | 0.0311 (8) | 0.5673 (7) | 1.0735 (4) | 0.053 (3) | |
C45 | −0.0803 (8) | 0.5336 (8) | 1.0477 (4) | 0.051 (3) | |
C46 | −0.1111 (7) | 0.4350 (7) | 0.9986 (4) | 0.048 (2) | |
C47 | −0.0670 (7) | 0.2662 (7) | 0.9204 (4) | 0.041 (2) | |
C51 | 0.2681 (7) | 0.3956 (7) | 0.9819 (4) | 0.046 (3) | |
C52 | 0.2865 (6) | 0.5259 (7) | 0.9671 (4) | 0.064 (3) | |
C53 | 0.3909 (6) | 0.5692 (6) | 0.9660 (4) | 0.060 (3) | |
C54 | 0.4753 (6) | 0.4786 (7) | 0.9787 (4) | 0.045 (2) | |
C55 | 0.4579 (6) | 0.3503 (6) | 0.9899 (3) | 0.052 (2) | |
C56 | 0.3541 (6) | 0.3096 (6) | 0.9917 (4) | 0.054 (2) | |
C58 | 0.6019 (7) | 0.6403 (7) | 0.9594 (5) | 0.086 (3) | |
O68 | 0.9411 (5) | 0.4901 (5) | 1.3087 (3) | 0.0518 (17) | |
O69 | 0.7720 (4) | 0.4446 (5) | 1.3161 (3) | 0.0492 (17) | |
O77 | 0.1817 (5) | 0.7652 (6) | 1.2270 (4) | 0.067 (2) | |
N70 | 0.6069 (6) | 0.5983 (6) | 1.2426 (4) | 0.056 (2) | |
C61 | 0.7927 (7) | 0.6130 (6) | 1.2369 (4) | 0.039 (2) | |
C62 | 0.6837 (7) | 0.6572 (6) | 1.2162 (4) | 0.043 (3) | |
C63 | 0.6551 (7) | 0.7581 (8) | 1.1689 (5) | 0.054 (3) | |
C64 | 0.7332 (7) | 0.8154 (7) | 1.1407 (4) | 0.052 (3) | |
C65 | 0.8424 (8) | 0.7721 (8) | 1.1622 (5) | 0.053 (3) | |
C66 | 0.8689 (7) | 0.6719 (7) | 1.2095 (4) | 0.046 (2) | |
C67 | 0.8330 (7) | 0.5093 (7) | 1.2906 (4) | 0.042 (3) | |
C71 | 0.5011 (6) | 0.6442 (7) | 1.2412 (4) | 0.046 (2) | |
C72 | 0.4702 (6) | 0.6587 (6) | 1.2992 (3) | 0.055 (2) | |
C73 | 0.3650 (6) | 0.6975 (7) | 1.2988 (3) | 0.056 (2) | |
C74 | 0.2857 (7) | 0.7243 (7) | 1.2353 (5) | 0.052 (3) | |
C75 | 0.3138 (6) | 0.7069 (6) | 1.1725 (3) | 0.0473 (19) | |
C76 | 0.4190 (6) | 0.6645 (6) | 1.1742 (3) | 0.0475 (19) | |
C78 | 0.1523 (7) | 0.7907 (9) | 1.2898 (5) | 0.091 (4) | |
H3 | 0.1853 | 0.0588 | 1.0638 | 0.057* | |
H4 | 0.0550 | 0.1507 | 1.1049 | 0.066* | |
H5 | −0.1224 | 0.0712 | 1.0746 | 0.068* | |
H6 | −0.1728 | −0.0996 | 0.9974 | 0.061* | |
H8 | −0.1823 | −0.3097 | 0.8760 | 0.072* | |
H10 | 0.1418 | −0.2002 | 0.9425 | 0.069* | |
H12 | 0.2502 | −0.0990 | 0.8702 | 0.066* | |
H13 | 0.4289 | −0.0429 | 0.8738 | 0.070* | |
H15 | 0.5059 | −0.0027 | 1.0823 | 0.058* | |
H16 | 0.3307 | −0.0631 | 1.0799 | 0.056* | |
H18A | 0.6285 | −0.0355 | 0.9015 | 0.111* | |
H18B | 0.6911 | 0.0930 | 0.9343 | 0.111* | |
H18C | 0.5656 | 0.0990 | 0.8910 | 0.111* | |
H23 | 0.5772 | 0.2840 | 1.1430 | 0.068* | |
H24 | 0.7091 | 0.3848 | 1.1010 | 0.076* | |
H25 | 0.8943 | 0.3273 | 1.1457 | 0.073* | |
H26 | 0.9439 | 0.1664 | 1.2300 | 0.061* | |
H28 | 0.9560 | −0.0585 | 1.3380 | 0.066* | |
H30 | 0.6194 | 0.0172 | 1.2485 | 0.068* | |
H32 | 0.5311 | 0.3325 | 1.2475 | 0.073* | |
H33 | 0.3561 | 0.4006 | 1.2469 | 0.084* | |
H35 | 0.2517 | 0.0297 | 1.2188 | 0.069* | |
H36 | 0.4242 | −0.0380 | 1.2162 | 0.060* | |
H38A | 0.2033 | 0.4009 | 1.2997 | 0.108* | |
H38B | 0.0828 | 0.3881 | 1.2486 | 0.108* | |
H38C | 0.1784 | 0.4393 | 1.2201 | 0.108* | |
H43 | 0.1819 | 0.5296 | 1.0706 | 0.065* | |
H44 | 0.0524 | 0.6335 | 1.1070 | 0.066* | |
H45 | −0.1331 | 0.5773 | 1.0634 | 0.065* | |
H46 | −0.1850 | 0.4101 | 0.9824 | 0.059* | |
H48 | −0.1893 | 0.1896 | 0.8679 | 0.067* | |
H50 | 0.1439 | 0.2727 | 0.9533 | 0.075* | |
H52 | 0.2281 | 0.5852 | 0.9576 | 0.081* | |
H53 | 0.4030 | 0.6567 | 0.9571 | 0.075* | |
H55 | 0.5152 | 0.2899 | 0.9962 | 0.066* | |
H56 | 0.3428 | 0.2216 | 0.9999 | 0.067* | |
H58A | 0.5483 | 0.6654 | 0.9161 | 0.108* | |
H58B | 0.6748 | 0.6461 | 0.9541 | 0.108* | |
H58C | 0.5966 | 0.6978 | 0.9966 | 0.108* | |
H63 | 0.5827 | 0.7890 | 1.1552 | 0.067* | |
H64 | 0.7122 | 0.8824 | 1.1076 | 0.065* | |
H65 | 0.8957 | 0.8104 | 1.1448 | 0.067* | |
H66 | 0.9415 | 0.6419 | 1.2239 | 0.058* | |
H68 | 0.9574 | 0.4272 | 1.3355 | 0.065* | |
H70 | 0.6257 | 0.5235 | 1.2627 | 0.070* | |
H72 | 0.5221 | 0.6420 | 1.3425 | 0.068* | |
H73 | 0.3476 | 0.7055 | 1.3409 | 0.070* | |
H75 | 0.2616 | 0.7238 | 1.1294 | 0.059* | |
H76 | 0.4362 | 0.6493 | 1.1325 | 0.059* | |
H78A | 0.1526 | 0.7099 | 1.3148 | 0.113* | |
H78B | 0.0797 | 0.8288 | 1.2778 | 0.113* | |
H78C | 0.2047 | 0.8504 | 1.3192 | 0.113* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O8 | 0.047 (3) | 0.057 (3) | 0.070 (4) | −0.014 (3) | 0.019 (3) | −0.025 (3) |
O9 | 0.057 (3) | 0.041 (3) | 0.065 (3) | −0.011 (3) | 0.029 (3) | −0.019 (3) |
O17 | 0.046 (3) | 0.082 (4) | 0.076 (4) | −0.008 (3) | 0.020 (3) | 0.017 (3) |
N10 | 0.045 (4) | 0.050 (4) | 0.073 (4) | −0.011 (3) | 0.023 (3) | −0.019 (3) |
C1 | 0.042 (4) | 0.032 (4) | 0.041 (4) | −0.007 (3) | 0.016 (3) | 0.002 (3) |
C2 | 0.049 (4) | 0.048 (4) | 0.034 (3) | −0.006 (4) | 0.015 (3) | 0.001 (3) |
C3 | 0.050 (4) | 0.037 (4) | 0.045 (4) | −0.008 (3) | 0.009 (3) | −0.012 (3) |
C4 | 0.066 (6) | 0.043 (4) | 0.046 (4) | 0.005 (4) | 0.011 (4) | −0.009 (3) |
C5 | 0.069 (6) | 0.048 (5) | 0.056 (5) | 0.002 (4) | 0.032 (4) | −0.012 (4) |
C6 | 0.056 (5) | 0.038 (4) | 0.063 (5) | 0.008 (4) | 0.035 (4) | −0.001 (3) |
C7 | 0.038 (4) | 0.040 (4) | 0.044 (4) | −0.001 (4) | 0.008 (3) | 0.007 (3) |
C11 | 0.052 (5) | 0.036 (4) | 0.053 (4) | −0.006 (3) | 0.016 (4) | −0.009 (3) |
C12 | 0.053 (4) | 0.066 (4) | 0.035 (3) | 0.003 (3) | 0.008 (3) | −0.004 (3) |
C13 | 0.054 (4) | 0.073 (5) | 0.042 (3) | 0.006 (4) | 0.017 (3) | 0.000 (3) |
C14 | 0.031 (4) | 0.051 (4) | 0.052 (4) | 0.010 (3) | 0.011 (3) | 0.015 (3) |
C15 | 0.046 (4) | 0.043 (4) | 0.042 (3) | 0.000 (3) | 0.001 (3) | 0.005 (3) |
C16 | 0.054 (4) | 0.040 (3) | 0.043 (3) | −0.003 (3) | 0.019 (3) | 0.002 (3) |
C18 | 0.059 (5) | 0.123 (7) | 0.100 (6) | 0.011 (5) | 0.046 (5) | 0.047 (6) |
O28 | 0.052 (3) | 0.045 (3) | 0.060 (3) | 0.005 (3) | 0.015 (3) | 0.014 (2) |
O29 | 0.049 (3) | 0.043 (3) | 0.053 (3) | 0.002 (3) | 0.009 (3) | 0.011 (2) |
O37 | 0.047 (3) | 0.071 (4) | 0.090 (4) | 0.005 (3) | 0.022 (3) | −0.007 (3) |
N30 | 0.053 (4) | 0.042 (4) | 0.066 (4) | 0.006 (3) | 0.013 (3) | 0.016 (3) |
C21 | 0.060 (5) | 0.032 (4) | 0.037 (3) | 0.002 (4) | 0.012 (3) | −0.003 (3) |
C22 | 0.048 (4) | 0.029 (4) | 0.046 (4) | 0.001 (3) | 0.004 (4) | 0.000 (3) |
C23 | 0.054 (5) | 0.043 (4) | 0.062 (5) | 0.010 (4) | 0.012 (4) | 0.012 (3) |
C24 | 0.079 (7) | 0.054 (5) | 0.048 (5) | 0.017 (5) | 0.017 (5) | 0.011 (4) |
C25 | 0.077 (7) | 0.050 (5) | 0.051 (4) | −0.012 (5) | 0.021 (5) | 0.008 (4) |
C26 | 0.053 (5) | 0.047 (4) | 0.045 (4) | 0.007 (4) | 0.012 (3) | 0.000 (3) |
C27 | 0.055 (5) | 0.030 (4) | 0.039 (4) | 0.008 (4) | 0.015 (3) | 0.003 (3) |
C31 | 0.042 (4) | 0.049 (4) | 0.045 (4) | 0.009 (4) | 0.008 (3) | 0.015 (3) |
C32 | 0.052 (4) | 0.035 (4) | 0.088 (5) | −0.005 (3) | 0.020 (4) | −0.007 (3) |
C33 | 0.071 (5) | 0.040 (4) | 0.094 (5) | 0.011 (4) | 0.030 (4) | −0.005 (4) |
C34 | 0.055 (5) | 0.046 (5) | 0.060 (5) | 0.003 (4) | 0.017 (4) | 0.010 (4) |
C35 | 0.053 (4) | 0.049 (4) | 0.058 (4) | −0.012 (3) | 0.008 (3) | 0.004 (3) |
C36 | 0.058 (4) | 0.039 (4) | 0.043 (3) | −0.006 (3) | 0.010 (3) | 0.003 (3) |
C38 | 0.066 (5) | 0.092 (7) | 0.116 (7) | 0.016 (5) | 0.047 (5) | −0.009 (5) |
O48 | 0.046 (3) | 0.052 (3) | 0.061 (3) | −0.014 (3) | 0.015 (3) | −0.021 (2) |
O49 | 0.051 (3) | 0.044 (3) | 0.062 (3) | −0.011 (3) | 0.021 (3) | −0.017 (3) |
O57 | 0.050 (4) | 0.063 (4) | 0.089 (4) | −0.007 (3) | 0.021 (3) | 0.005 (3) |
N50 | 0.049 (4) | 0.047 (4) | 0.086 (5) | −0.012 (3) | 0.025 (4) | −0.020 (4) |
C41 | 0.038 (4) | 0.039 (4) | 0.043 (4) | −0.009 (3) | 0.015 (3) | −0.004 (3) |
C42 | 0.050 (5) | 0.035 (4) | 0.048 (4) | −0.006 (4) | 0.020 (4) | −0.005 (3) |
C43 | 0.060 (5) | 0.050 (5) | 0.042 (4) | −0.009 (4) | 0.007 (4) | −0.011 (3) |
C44 | 0.072 (6) | 0.039 (4) | 0.048 (4) | 0.002 (4) | 0.020 (4) | −0.016 (4) |
C45 | 0.060 (6) | 0.048 (5) | 0.053 (4) | −0.002 (4) | 0.027 (4) | −0.003 (4) |
C46 | 0.050 (4) | 0.044 (4) | 0.052 (4) | 0.000 (4) | 0.018 (4) | −0.001 (3) |
C47 | 0.042 (4) | 0.037 (4) | 0.044 (4) | −0.001 (3) | 0.014 (3) | 0.001 (3) |
C51 | 0.048 (5) | 0.035 (4) | 0.057 (4) | −0.005 (4) | 0.019 (4) | −0.008 (3) |
C52 | 0.052 (4) | 0.047 (4) | 0.096 (6) | 0.003 (4) | 0.025 (4) | −0.002 (4) |
C53 | 0.052 (4) | 0.044 (4) | 0.086 (5) | −0.003 (3) | 0.023 (4) | −0.001 (3) |
C54 | 0.036 (4) | 0.048 (4) | 0.050 (4) | 0.002 (3) | 0.012 (3) | 0.005 (3) |
C55 | 0.049 (4) | 0.046 (4) | 0.058 (4) | 0.002 (3) | 0.009 (3) | 0.010 (3) |
C56 | 0.056 (4) | 0.037 (4) | 0.062 (4) | −0.005 (3) | 0.008 (3) | −0.003 (3) |
C58 | 0.067 (5) | 0.081 (6) | 0.109 (7) | −0.022 (5) | 0.024 (5) | −0.003 (5) |
O68 | 0.052 (3) | 0.048 (3) | 0.055 (3) | 0.005 (3) | 0.015 (3) | 0.010 (2) |
O69 | 0.045 (3) | 0.042 (3) | 0.058 (3) | 0.003 (3) | 0.011 (3) | 0.011 (2) |
O77 | 0.042 (3) | 0.079 (4) | 0.081 (4) | 0.002 (3) | 0.019 (3) | −0.007 (3) |
N70 | 0.052 (4) | 0.043 (4) | 0.076 (4) | 0.012 (3) | 0.023 (4) | 0.027 (3) |
C61 | 0.053 (5) | 0.028 (4) | 0.037 (3) | −0.003 (3) | 0.013 (3) | −0.002 (3) |
C62 | 0.051 (5) | 0.025 (4) | 0.051 (4) | −0.002 (3) | 0.012 (4) | 0.002 (3) |
C63 | 0.051 (5) | 0.049 (5) | 0.063 (5) | 0.003 (4) | 0.019 (4) | 0.010 (4) |
C64 | 0.063 (6) | 0.045 (4) | 0.051 (4) | 0.012 (4) | 0.021 (4) | 0.011 (4) |
C65 | 0.059 (5) | 0.049 (4) | 0.054 (4) | −0.007 (4) | 0.021 (4) | 0.011 (4) |
C66 | 0.050 (4) | 0.044 (4) | 0.044 (4) | 0.009 (4) | 0.012 (3) | 0.004 (3) |
C67 | 0.051 (5) | 0.032 (4) | 0.044 (4) | 0.009 (4) | 0.014 (4) | −0.004 (3) |
C71 | 0.046 (4) | 0.049 (4) | 0.040 (4) | 0.001 (4) | 0.009 (3) | 0.012 (3) |
C72 | 0.052 (4) | 0.056 (4) | 0.051 (4) | 0.001 (3) | 0.007 (3) | 0.008 (3) |
C73 | 0.053 (4) | 0.070 (4) | 0.047 (3) | 0.008 (4) | 0.016 (3) | −0.005 (3) |
C74 | 0.055 (5) | 0.041 (4) | 0.056 (5) | −0.003 (4) | 0.011 (4) | 0.001 (4) |
C75 | 0.040 (3) | 0.053 (4) | 0.046 (3) | −0.005 (3) | 0.008 (3) | −0.003 (3) |
C76 | 0.054 (4) | 0.045 (3) | 0.041 (3) | −0.005 (3) | 0.010 (3) | 0.001 (3) |
C78 | 0.068 (5) | 0.109 (7) | 0.108 (7) | −0.002 (5) | 0.046 (5) | −0.033 (6) |
Geometric parameters (Å, º) top
O8—C7 | 1.321 (11) | C31—C36 | 1.411 (10) |
O9—C7 | 1.226 (10) | C32—C33 | 1.396 (12) |
O17—C14 | 1.394 (10) | C33—C34 | 1.381 (13) |
O17—C18 | 1.421 (11) | C34—C35 | 1.380 (10) |
O8—H8 | 0.820 | C35—C36 | 1.380 (11) |
O28—C27 | 1.321 (11) | C23—H23 | 0.930 |
O29—C27 | 1.242 (10) | C24—H24 | 0.930 |
O37—C34 | 1.348 (12) | C25—H25 | 0.930 |
O37—C38 | 1.417 (10) | C26—H26 | 0.930 |
O28—H28 | 0.820 | C32—H32 | 0.930 |
O48—C47 | 1.322 (10) | C33—H33 | 0.930 |
O49—C47 | 1.229 (10) | C35—H35 | 0.930 |
O57—C58 | 1.411 (10) | C36—H36 | 0.930 |
O57—C54 | 1.396 (10) | C38—H38B | 0.960 |
O48—H48 | 0.820 | C38—H38A | 0.960 |
O68—C67 | 1.322 (11) | C38—H38C | 0.960 |
O69—C67 | 1.232 (10) | C41—C47 | 1.459 (10) |
O77—C74 | 1.343 (11) | C41—C42 | 1.434 (12) |
O77—C78 | 1.426 (12) | C41—C46 | 1.408 (12) |
O68—H68 | 0.820 | C42—C43 | 1.426 (10) |
N10—C2 | 1.395 (11) | C43—C44 | 1.340 (13) |
N10—C11 | 1.413 (11) | C44—C45 | 1.393 (14) |
N10—H10 | 0.860 | C45—C46 | 1.374 (11) |
N30—C31 | 1.425 (11) | C51—C52 | 1.394 (10) |
N30—C22 | 1.371 (11) | C51—C56 | 1.365 (11) |
N30—H30 | 0.860 | C52—C53 | 1.399 (11) |
N50—C42 | 1.368 (11) | C53—C54 | 1.377 (10) |
N50—C51 | 1.410 (12) | C54—C55 | 1.355 (9) |
N50—H50 | 0.860 | C55—C56 | 1.388 (11) |
N70—C62 | 1.371 (11) | C43—H43 | 0.930 |
N70—C71 | 1.410 (11) | C44—H44 | 0.930 |
N70—H70 | 0.860 | C45—H45 | 0.930 |
C1—C7 | 1.455 (9) | C46—H46 | 0.930 |
C1—C6 | 1.407 (11) | C52—H52 | 0.930 |
C1—C2 | 1.442 (12) | C53—H53 | 0.930 |
C2—C3 | 1.428 (10) | C55—H55 | 0.930 |
C3—C4 | 1.339 (12) | C56—H56 | 0.930 |
C4—C5 | 1.375 (13) | C58—H58A | 0.960 |
C5—C6 | 1.364 (11) | C58—H58C | 0.960 |
C11—C12 | 1.434 (10) | C58—H58B | 0.960 |
C11—C16 | 1.338 (10) | C61—C66 | 1.377 (12) |
C12—C13 | 1.375 (11) | C61—C67 | 1.481 (10) |
C13—C14 | 1.380 (10) | C61—C62 | 1.392 (12) |
C14—C15 | 1.362 (10) | C62—C63 | 1.367 (11) |
C15—C16 | 1.373 (10) | C63—C64 | 1.399 (13) |
C3—H3 | 0.930 | C64—C65 | 1.392 (14) |
C4—H4 | 0.930 | C65—C66 | 1.361 (11) |
C5—H5 | 0.930 | C71—C76 | 1.441 (10) |
C6—H6 | 0.930 | C71—C72 | 1.329 (10) |
C12—H12 | 0.930 | C72—C73 | 1.386 (11) |
C13—H13 | 0.930 | C73—C74 | 1.387 (11) |
C15—H15 | 0.930 | C74—C75 | 1.405 (11) |
C16—H16 | 0.930 | C75—C76 | 1.390 (11) |
C18—H18B | 0.960 | C63—H63 | 0.930 |
C18—H18A | 0.960 | C64—H64 | 0.930 |
C18—H18C | 0.960 | C65—H65 | 0.930 |
C21—C22 | 1.396 (12) | C66—H66 | 0.930 |
C21—C27 | 1.463 (10) | C72—H72 | 0.930 |
C21—C26 | 1.387 (12) | C73—H73 | 0.930 |
C22—C23 | 1.389 (11) | C75—H75 | 0.930 |
C23—C24 | 1.389 (13) | C76—H76 | 0.930 |
C24—C25 | 1.386 (14) | C78—H78A | 0.960 |
C25—C26 | 1.371 (11) | C78—H78B | 0.960 |
C31—C32 | 1.350 (10) | C78—H78C | 0.960 |
| | | |
C14—O17—C18 | 117.8 (6) | C34—C35—H35 | 119.1 |
C7—O8—H8 | 109.5 | C36—C35—H35 | 119.1 |
C34—O37—C38 | 118.0 (7) | C35—C36—H36 | 120.4 |
C27—O28—H28 | 109.4 | C31—C36—H36 | 120.5 |
C54—O57—C58 | 118.0 (7) | O37—C38—H38A | 109.5 |
C47—O48—H48 | 109.4 | O37—C38—H38B | 109.4 |
C74—O77—C78 | 116.6 (8) | H38A—C38—H38C | 109.5 |
C67—O68—H68 | 109.5 | H38B—C38—H38C | 109.5 |
C2—N10—C11 | 127.4 (7) | H38A—C38—H38B | 109.5 |
C11—N10—H10 | 116.3 | O37—C38—H38C | 109.5 |
C2—N10—H10 | 116.2 | C42—C41—C46 | 119.9 (7) |
C22—N30—C31 | 127.5 (6) | C42—C41—C47 | 119.7 (7) |
C31—N30—H30 | 116.2 | C46—C41—C47 | 120.4 (7) |
C22—N30—H30 | 116.3 | C41—C42—C43 | 115.8 (8) |
C42—N50—C51 | 125.9 (7) | N50—C42—C41 | 122.0 (7) |
C51—N50—H50 | 117.0 | N50—C42—C43 | 122.2 (8) |
C42—N50—H50 | 117.0 | C42—C43—C44 | 122.8 (9) |
C62—N70—C71 | 128.5 (6) | C43—C44—C45 | 121.2 (7) |
C71—N70—H70 | 115.8 | C44—C45—C46 | 119.0 (9) |
C62—N70—H70 | 115.7 | C41—C46—C45 | 121.2 (8) |
C6—C1—C7 | 121.0 (7) | O48—C47—C41 | 114.0 (7) |
C2—C1—C7 | 120.9 (7) | O49—C47—C41 | 125.8 (8) |
C2—C1—C6 | 118.1 (6) | O48—C47—O49 | 120.2 (7) |
N10—C2—C3 | 123.0 (8) | C52—C51—C56 | 117.8 (8) |
N10—C2—C1 | 119.5 (6) | N50—C51—C52 | 122.0 (7) |
C1—C2—C3 | 117.4 (7) | N50—C51—C56 | 119.3 (6) |
C2—C3—C4 | 121.1 (8) | C51—C52—C53 | 121.4 (7) |
C3—C4—C5 | 121.8 (7) | C52—C53—C54 | 118.1 (6) |
C4—C5—C6 | 119.9 (9) | O57—C54—C55 | 115.6 (7) |
C1—C6—C5 | 121.6 (8) | C53—C54—C55 | 121.5 (7) |
O9—C7—C1 | 125.7 (8) | O57—C54—C53 | 122.8 (7) |
O8—C7—O9 | 120.4 (7) | C54—C55—C56 | 119.6 (7) |
O8—C7—C1 | 113.9 (7) | C51—C56—C55 | 121.7 (6) |
C12—C11—C16 | 118.6 (8) | C42—C43—H43 | 118.6 |
N10—C11—C16 | 126.7 (7) | C44—C43—H43 | 118.6 |
N10—C11—C12 | 114.7 (7) | C45—C44—H44 | 119.4 |
C11—C12—C13 | 119.8 (6) | C43—C44—H44 | 119.4 |
C12—C13—C14 | 119.4 (6) | C46—C45—H45 | 120.4 |
C13—C14—C15 | 120.0 (7) | C44—C45—H45 | 120.5 |
O17—C14—C13 | 123.3 (7) | C41—C46—H46 | 119.4 |
O17—C14—C15 | 116.7 (6) | C45—C46—H46 | 119.4 |
C14—C15—C16 | 121.0 (6) | C53—C52—H52 | 119.3 |
C11—C16—C15 | 121.2 (6) | C51—C52—H52 | 119.3 |
C4—C3—H3 | 119.5 | C54—C53—H53 | 121.0 |
C2—C3—H3 | 119.4 | C52—C53—H53 | 121.0 |
C5—C4—H4 | 119.1 | C56—C55—H55 | 120.3 |
C3—C4—H4 | 119.1 | C54—C55—H55 | 120.2 |
C6—C5—H5 | 120.0 | C55—C56—H56 | 119.2 |
C4—C5—H5 | 120.1 | C51—C56—H56 | 119.1 |
C5—C6—H6 | 119.2 | H58B—C58—H58C | 109.5 |
C1—C6—H6 | 119.2 | H58A—C58—H58B | 109.5 |
C11—C12—H12 | 120.0 | H58A—C58—H58C | 109.5 |
C13—C12—H12 | 120.1 | O57—C58—H58C | 109.4 |
C12—C13—H13 | 120.3 | O57—C58—H58A | 109.5 |
C14—C13—H13 | 120.3 | O57—C58—H58B | 109.5 |
C14—C15—H15 | 119.6 | C62—C61—C66 | 119.4 (7) |
C16—C15—H15 | 119.5 | C62—C61—C67 | 123.0 (8) |
C11—C16—H16 | 119.4 | C66—C61—C67 | 117.6 (8) |
C15—C16—H16 | 119.4 | N70—C62—C63 | 121.2 (8) |
O17—C18—H18A | 109.5 | N70—C62—C61 | 119.8 (6) |
H18A—C18—H18C | 109.5 | C61—C62—C63 | 119.0 (8) |
O17—C18—H18B | 109.5 | C62—C63—C64 | 120.9 (8) |
H18A—C18—H18B | 109.5 | C63—C64—C65 | 119.9 (7) |
H18B—C18—H18C | 109.5 | C64—C65—C66 | 118.0 (9) |
O17—C18—H18C | 109.4 | C61—C66—C65 | 122.8 (8) |
C22—C21—C26 | 118.6 (7) | O69—C67—C61 | 123.6 (8) |
C26—C21—C27 | 117.7 (8) | O68—C67—C61 | 114.2 (7) |
C22—C21—C27 | 123.8 (8) | O68—C67—O69 | 122.2 (7) |
N30—C22—C23 | 120.6 (8) | N70—C71—C72 | 122.7 (7) |
C21—C22—C23 | 119.6 (8) | N70—C71—C76 | 119.2 (7) |
N30—C22—C21 | 119.7 (7) | C72—C71—C76 | 117.9 (7) |
C22—C23—C24 | 120.3 (8) | C71—C72—C73 | 123.6 (6) |
C23—C24—C25 | 120.5 (8) | C72—C73—C74 | 119.8 (6) |
C24—C25—C26 | 118.6 (9) | O77—C74—C75 | 115.2 (8) |
C21—C26—C25 | 122.4 (8) | O77—C74—C73 | 126.3 (8) |
O28—C27—C21 | 115.5 (7) | C73—C74—C75 | 118.5 (8) |
O29—C27—C21 | 122.9 (8) | C74—C75—C76 | 120.6 (6) |
O28—C27—O29 | 121.5 (7) | C71—C76—C75 | 119.4 (6) |
N30—C31—C36 | 117.2 (6) | C62—C63—H63 | 119.5 |
N30—C31—C32 | 123.7 (7) | C64—C63—H63 | 119.6 |
C32—C31—C36 | 119.1 (7) | C63—C64—H64 | 120.0 |
C31—C32—C33 | 121.5 (7) | C65—C64—H64 | 120.0 |
C32—C33—C34 | 120.0 (7) | C64—C65—H65 | 121.1 |
O37—C34—C35 | 116.4 (8) | C66—C65—H65 | 120.9 |
C33—C34—C35 | 118.5 (9) | C61—C66—H66 | 118.6 |
O37—C34—C33 | 125.0 (8) | C65—C66—H66 | 118.6 |
C34—C35—C36 | 121.7 (7) | C71—C72—H72 | 118.2 |
C31—C36—C35 | 119.1 (6) | C73—C72—H72 | 118.2 |
C22—C23—H23 | 119.8 | C72—C73—H73 | 120.2 |
C24—C23—H23 | 119.9 | C74—C73—H73 | 120.1 |
C25—C24—H24 | 119.7 | C74—C75—H75 | 119.8 |
C23—C24—H24 | 119.8 | C76—C75—H75 | 119.7 |
C26—C25—H25 | 120.7 | C71—C76—H76 | 120.3 |
C24—C25—H25 | 120.7 | C75—C76—H76 | 120.3 |
C25—C26—H26 | 118.8 | O77—C78—H78A | 109.5 |
C21—C26—H26 | 118.8 | O77—C78—H78B | 109.5 |
C33—C32—H32 | 119.3 | O77—C78—H78C | 109.6 |
C31—C32—H32 | 119.3 | H78A—C78—H78B | 109.4 |
C32—C33—H33 | 120.0 | H78A—C78—H78C | 109.4 |
C34—C33—H33 | 120.0 | H78B—C78—H78C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O8—H8···O69i | 0.82 | 1.80 | 2.612 (8) | 172 |
N10—H10···O9 | 0.86 | 1.97 | 2.662 (9) | 137 |
O28—H28···O49ii | 0.82 | 1.82 | 2.644 (8) | 178 |
N30—H30···O29 | 0.86 | 2.05 | 2.669 (9) | 128 |
O48—H48···O29i | 0.82 | 1.79 | 2.608 (8) | 174 |
N50—H50···O49 | 0.86 | 2.03 | 2.673 (9) | 131 |
O68—H68···O9ii | 0.82 | 1.85 | 2.666 (8) | 176 |
N70—H70···O69 | 0.86 | 2.01 | 2.673 (9) | 133 |
C26—H26···O28 | 0.93 | 2.31 | 2.678 (9) | 103 |
C46—H46···O48 | 0.93 | 2.39 | 2.714 (9) | 100 |
C66—H66···O68 | 0.93 | 2.29 | 2.662 (9) | 103 |
Symmetry codes: (i) x−1, −y, z−1/2; (ii) x+1, −y, z+1/2. |
Experimental details
Crystal data |
Chemical formula | C14H13NO3 |
Mr | 243.25 |
Crystal system, space group | Monoclinic, Pc |
Temperature (K) | 293 |
a, b, c (Å) | 12.6506 (6), 10.1894 (5), 19.8565 (12) |
β (°) | 107.160 (5) |
V (Å3) | 2445.6 (2) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 0.77 |
Crystal size (mm) | 0.50 × 0.22 × 0.08 |
|
Data collection |
Diffractometer | Siemens P4 four-circle diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.699, 0.940 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 5863, 4933, 3152 |
Rint | 0.053 |
(sin θ/λ)max (Å−1) | 0.606 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.155, 1.05 |
No. of reflections | 4933 |
No. of parameters | 658 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.18 |
Selected geometric parameters (Å, º) topO8—C7 | 1.321 (11) | O68—C67 | 1.322 (11) |
O9—C7 | 1.226 (10) | O69—C67 | 1.232 (10) |
O17—C14 | 1.394 (10) | O77—C74 | 1.343 (11) |
O17—C18 | 1.421 (11) | O77—C78 | 1.426 (12) |
O28—C27 | 1.321 (11) | N10—C2 | 1.395 (11) |
O29—C27 | 1.242 (10) | N10—C11 | 1.413 (11) |
O37—C34 | 1.348 (12) | N30—C31 | 1.425 (11) |
O37—C38 | 1.417 (10) | N30—C22 | 1.371 (11) |
O48—C47 | 1.322 (10) | N50—C42 | 1.368 (11) |
O49—C47 | 1.229 (10) | N50—C51 | 1.410 (12) |
O57—C58 | 1.411 (10) | N70—C62 | 1.371 (11) |
O57—C54 | 1.396 (10) | N70—C71 | 1.410 (11) |
| | | |
C14—O17—C18 | 117.8 (6) | N30—C31—C36 | 117.2 (6) |
C34—O37—C38 | 118.0 (7) | N30—C31—C32 | 123.7 (7) |
C54—O57—C58 | 118.0 (7) | O37—C34—C35 | 116.4 (8) |
C74—O77—C78 | 116.6 (8) | O37—C34—C33 | 125.0 (8) |
C2—N10—C11 | 127.4 (7) | N50—C42—C41 | 122.0 (7) |
C22—N30—C31 | 127.5 (6) | N50—C42—C43 | 122.2 (8) |
C42—N50—C51 | 125.9 (7) | O48—C47—C41 | 114.0 (7) |
C62—N70—C71 | 128.5 (6) | O49—C47—C41 | 125.8 (8) |
N10—C2—C3 | 123.0 (8) | O48—C47—O49 | 120.2 (7) |
N10—C2—C1 | 119.5 (6) | N50—C51—C52 | 122.0 (7) |
O9—C7—C1 | 125.7 (8) | N50—C51—C56 | 119.3 (6) |
O8—C7—O9 | 120.4 (7) | O57—C54—C55 | 115.6 (7) |
O8—C7—C1 | 113.9 (7) | O57—C54—C53 | 122.8 (7) |
N10—C11—C16 | 126.7 (7) | N70—C62—C63 | 121.2 (8) |
N10—C11—C12 | 114.7 (7) | N70—C62—C61 | 119.8 (6) |
O17—C14—C13 | 123.3 (7) | O69—C67—C61 | 123.6 (8) |
O17—C14—C15 | 116.7 (6) | O68—C67—C61 | 114.2 (7) |
N30—C22—C23 | 120.6 (8) | O68—C67—O69 | 122.2 (7) |
N30—C22—C21 | 119.7 (7) | N70—C71—C72 | 122.7 (7) |
O28—C27—C21 | 115.5 (7) | N70—C71—C76 | 119.2 (7) |
O29—C27—C21 | 122.9 (8) | O77—C74—C75 | 115.2 (8) |
O28—C27—O29 | 121.5 (7) | O77—C74—C73 | 126.3 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O8—H8···O69i | 0.82 | 1.80 | 2.612 (8) | 172 |
N10—H10···O9 | 0.86 | 1.97 | 2.662 (9) | 137 |
O28—H28···O49ii | 0.82 | 1.82 | 2.644 (8) | 178 |
N30—H30···O29 | 0.86 | 2.05 | 2.669 (9) | 128 |
O48—H48···O29i | 0.82 | 1.79 | 2.608 (8) | 174 |
N50—H50···O49 | 0.86 | 2.03 | 2.673 (9) | 131 |
O68—H68···O9ii | 0.82 | 1.85 | 2.666 (8) | 176 |
N70—H70···O69 | 0.86 | 2.01 | 2.673 (9) | 133 |
C26—H26···O28 | 0.93 | 2.31 | 2.678 (9) | 103 |
C46—H46···O48 | 0.93 | 2.39 | 2.714 (9) | 100 |
C66—H66···O68 | 0.93 | 2.29 | 2.662 (9) | 103 |
Symmetry codes: (i) x−1, −y, z−1/2; (ii) x+1, −y, z+1/2. |
2-(4-Methoxyphenyl)aminobenzoic acid, (I), is used as an intermediate in the synthesis of acridones. Fig. 1 shows the atom-numbering scheme used. An internal N—H···O hydrogen bond with the imino N atom as donor and the carbonyl O atom as acceptor is present. The imino group is not involved in intermolecular interactions, which is a common feature of related compounds such as fenamates (Dhanaraj & Vijayan, 1988). The carboxyl groups are, therefore, the only site for intermolecular interactions. Dimerization occurs through hydrogen bonding of carboxylic acid groups (Fig. 1).
The structure has four molecules in the asymmetric unit, which is quite unusual. There is a pseudo-centre of symmetry involving the carboxyphenyl amide groups of independent molecules, but the 4-methoxyphenyl group is rotated about N30—C31 in different directions and by different amounts for each molecule.