Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801010364/cf6085sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801010364/cf6085Isup2.hkl |
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).
Fig. 1. Plot of (I) showing the atomic numbering scheme. Displacement ellipsoids are drawn at 50% probability level for non-H atoms. |
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 |
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 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) |
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)° |
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 |
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 |
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 |
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* |
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) |
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 |
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 |
Computer programs: XSCANS (Siemens, 1996), XSCANS, SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), DIAMOND (Bergerhoff, 1996), PARST (Nardelli, 1991) and PLATON (Spek, 1990).
O8—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) |
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. |
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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.