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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801010364/cf6085sup1.cif
Contains datablocks X, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801010364/cf6085Isup2.hkl
Contains datablock I

CCDC reference: 170780

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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.

Comment top

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.

Experimental top

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.

Refinement top

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.

Computing details top

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).

Figures top
[Figure 1] Fig. 1. Plot of (I) showing the atomic numbering scheme. Displacement ellipsoids are drawn at 50% probability level for non-H atoms.
2-(4-methoxyphenyl)aminobenzoic acid top
Crystal data top
C14H13NO3F(000) = 1024
Mr = 243.25Dx = 1.321 Mg m3
Monoclinic, PcCu Kα radiation, λ = 1.54180 Å
a = 12.6506 (6) ÅCell parameters from 39 reflections
b = 10.1894 (5) Åθ = 10.6–27.7°
c = 19.8565 (12) ŵ = 0.77 mm1
β = 107.160 (5)°T = 293 K
V = 2445.6 (2) Å3Plate, black
Z = 80.50 × 0.22 × 0.08 mm
Data collection top
Siemens P4 four-circle
diffractometer
Rint = 0.053
ω/2θ scansθmax = 69.1°
Absorption correction: ψ scan
(North et al., 1968)
h = 151
Tmin = 0.699, Tmax = 0.940k = 112
5863 measured reflectionsl = 2324
4933 independent reflections3 standard reflections every 100 reflections
3152 reflections with F2 > 2σ(F2) intensity decay: 0.0%
Refinement top
Refinement on F2H-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) = 0.155Δρmax = 0.20 e Å3
S = 1.05Δρmin = 0.18 e Å3
4933 reflectionsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin((2θ)]-1/4
658 parametersExtinction coefficient: 0.0010 (2)
Crystal data top
C14H13NO3V = 2445.6 (2) Å3
Mr = 243.25Z = 8
Monoclinic, PcCu Kα radiation
a = 12.6506 (6) ŵ = 0.77 mm1
b = 10.1894 (5) ÅT = 293 K
c = 19.8565 (12) Å0.50 × 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 = 0.9403 standard reflections every 100 reflections
5863 measured reflections intensity decay: 0.0%
4933 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.053658 parameters
wR(F2) = 0.155H-atom parameters constrained
S = 1.05Δρmax = 0.20 e Å3
4933 reflectionsΔρmin = 0.18 e Å3
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
xyzUiso*/Ueq
O80.1675 (5)0.2522 (6)0.9062 (3)0.0576 (19)
O90.0010 (5)0.2921 (5)0.8998 (3)0.0520 (17)
O170.5920 (5)0.0251 (6)0.9857 (3)0.068 (2)
N100.1637 (5)0.1329 (6)0.9690 (4)0.055 (2)
C10.0252 (6)0.1262 (6)0.9783 (3)0.038 (2)
C20.0869 (7)0.0779 (7)0.9988 (4)0.043 (2)
C30.1133 (7)0.0269 (7)1.0487 (4)0.045 (2)
C40.0360 (7)0.0802 (7)1.0740 (4)0.053 (3)
C50.0707 (8)0.0335 (8)1.0555 (4)0.055 (3)
C60.1007 (7)0.0680 (7)1.0090 (4)0.049 (3)
C70.0599 (7)0.2298 (7)0.9260 (4)0.042 (2)
C110.2732 (7)0.0905 (7)0.9774 (4)0.047 (3)
C120.3026 (6)0.0812 (6)0.9131 (3)0.052 (2)
C130.4084 (6)0.0458 (7)0.9151 (3)0.056 (2)
C140.4839 (6)0.0146 (7)0.9789 (4)0.045 (2)
C150.4543 (5)0.0226 (6)1.0394 (3)0.046 (2)
C160.3493 (6)0.0596 (6)1.0380 (3)0.0447 (19)
C180.6217 (7)0.0472 (9)0.9230 (5)0.089 (3)
O280.9406 (5)0.0036 (5)1.3105 (3)0.0527 (17)
O290.7693 (4)0.0515 (5)1.3102 (3)0.0496 (17)
O370.1828 (5)0.2495 (6)1.2364 (4)0.069 (2)
N300.6029 (6)0.0958 (6)1.2331 (3)0.055 (2)
C210.7921 (7)0.1228 (7)1.2360 (4)0.043 (2)
C220.6814 (7)0.1610 (7)1.2109 (4)0.043 (2)
C230.6510 (7)0.2591 (7)1.1603 (5)0.054 (3)
C240.7303 (8)0.3202 (8)1.1355 (4)0.061 (3)
C250.8408 (8)0.2856 (8)1.1617 (5)0.059 (3)
C260.8696 (7)0.1887 (7)1.2117 (4)0.049 (3)
C270.8321 (7)0.0188 (7)1.2881 (4)0.041 (3)
C310.4971 (6)0.1431 (7)1.2336 (4)0.046 (2)
C320.4750 (6)0.2707 (6)1.2418 (4)0.058 (3)
C330.3698 (7)0.3120 (7)1.2419 (4)0.067 (3)
C340.2861 (8)0.2213 (8)1.2347 (5)0.054 (3)
C350.3080 (6)0.0912 (6)1.2248 (3)0.055 (2)
C360.4113 (6)0.0500 (6)1.2235 (3)0.048 (2)
C380.1600 (7)0.3800 (8)1.2525 (5)0.087 (4)
O480.1754 (4)0.2507 (5)0.8959 (3)0.0532 (17)
O490.0049 (5)0.1977 (5)0.8979 (3)0.0514 (17)
O570.5815 (5)0.5101 (6)0.9763 (4)0.067 (2)
N500.1610 (6)0.3467 (6)0.9746 (4)0.060 (3)
C410.0328 (6)0.3711 (7)0.9723 (4)0.039 (2)
C420.0818 (7)0.4063 (7)0.9983 (4)0.043 (3)
C430.1081 (8)0.5060 (7)1.0510 (4)0.052 (3)
C440.0311 (8)0.5673 (7)1.0735 (4)0.053 (3)
C450.0803 (8)0.5336 (8)1.0477 (4)0.051 (3)
C460.1111 (7)0.4350 (7)0.9986 (4)0.048 (2)
C470.0670 (7)0.2662 (7)0.9204 (4)0.041 (2)
C510.2681 (7)0.3956 (7)0.9819 (4)0.046 (3)
C520.2865 (6)0.5259 (7)0.9671 (4)0.064 (3)
C530.3909 (6)0.5692 (6)0.9660 (4)0.060 (3)
C540.4753 (6)0.4786 (7)0.9787 (4)0.045 (2)
C550.4579 (6)0.3503 (6)0.9899 (3)0.052 (2)
C560.3541 (6)0.3096 (6)0.9917 (4)0.054 (2)
C580.6019 (7)0.6403 (7)0.9594 (5)0.086 (3)
O680.9411 (5)0.4901 (5)1.3087 (3)0.0518 (17)
O690.7720 (4)0.4446 (5)1.3161 (3)0.0492 (17)
O770.1817 (5)0.7652 (6)1.2270 (4)0.067 (2)
N700.6069 (6)0.5983 (6)1.2426 (4)0.056 (2)
C610.7927 (7)0.6130 (6)1.2369 (4)0.039 (2)
C620.6837 (7)0.6572 (6)1.2162 (4)0.043 (3)
C630.6551 (7)0.7581 (8)1.1689 (5)0.054 (3)
C640.7332 (7)0.8154 (7)1.1407 (4)0.052 (3)
C650.8424 (8)0.7721 (8)1.1622 (5)0.053 (3)
C660.8689 (7)0.6719 (7)1.2095 (4)0.046 (2)
C670.8330 (7)0.5093 (7)1.2906 (4)0.042 (3)
C710.5011 (6)0.6442 (7)1.2412 (4)0.046 (2)
C720.4702 (6)0.6587 (6)1.2992 (3)0.055 (2)
C730.3650 (6)0.6975 (7)1.2988 (3)0.056 (2)
C740.2857 (7)0.7243 (7)1.2353 (5)0.052 (3)
C750.3138 (6)0.7069 (6)1.1725 (3)0.0473 (19)
C760.4190 (6)0.6645 (6)1.1742 (3)0.0475 (19)
C780.1523 (7)0.7907 (9)1.2898 (5)0.091 (4)
H30.18530.05881.06380.057*
H40.05500.15071.10490.066*
H50.12240.07121.07460.068*
H60.17280.09960.99740.061*
H80.18230.30970.87600.072*
H100.14180.20020.94250.069*
H120.25020.09900.87020.066*
H130.42890.04290.87380.070*
H150.50590.00271.08230.058*
H160.33070.06311.07990.056*
H18A0.62850.03550.90150.111*
H18B0.69110.09300.93430.111*
H18C0.56560.09900.89100.111*
H230.57720.28401.14300.068*
H240.70910.38481.10100.076*
H250.89430.32731.14570.073*
H260.94390.16641.23000.061*
H280.95600.05851.33800.066*
H300.61940.01721.24850.068*
H320.53110.33251.24750.073*
H330.35610.40061.24690.084*
H350.25170.02971.21880.069*
H360.42420.03801.21620.060*
H38A0.20330.40091.29970.108*
H38B0.08280.38811.24860.108*
H38C0.17840.43931.22010.108*
H430.18190.52961.07060.065*
H440.05240.63351.10700.066*
H450.13310.57731.06340.065*
H460.18500.41010.98240.059*
H480.18930.18960.86790.067*
H500.14390.27270.95330.075*
H520.22810.58520.95760.081*
H530.40300.65670.95710.075*
H550.51520.28990.99620.066*
H560.34280.22160.99990.067*
H58A0.54830.66540.91610.108*
H58B0.67480.64610.95410.108*
H58C0.59660.69780.99660.108*
H630.58270.78901.15520.067*
H640.71220.88241.10760.065*
H650.89570.81041.14480.067*
H660.94150.64191.22390.058*
H680.95740.42721.33550.065*
H700.62570.52351.26270.070*
H720.52210.64201.34250.068*
H730.34760.70551.34090.070*
H750.26160.72381.12940.059*
H760.43620.64931.13250.059*
H78A0.15260.70991.31480.113*
H78B0.07970.82881.27780.113*
H78C0.20470.85041.31920.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O80.047 (3)0.057 (3)0.070 (4)0.014 (3)0.019 (3)0.025 (3)
O90.057 (3)0.041 (3)0.065 (3)0.011 (3)0.029 (3)0.019 (3)
O170.046 (3)0.082 (4)0.076 (4)0.008 (3)0.020 (3)0.017 (3)
N100.045 (4)0.050 (4)0.073 (4)0.011 (3)0.023 (3)0.019 (3)
C10.042 (4)0.032 (4)0.041 (4)0.007 (3)0.016 (3)0.002 (3)
C20.049 (4)0.048 (4)0.034 (3)0.006 (4)0.015 (3)0.001 (3)
C30.050 (4)0.037 (4)0.045 (4)0.008 (3)0.009 (3)0.012 (3)
C40.066 (6)0.043 (4)0.046 (4)0.005 (4)0.011 (4)0.009 (3)
C50.069 (6)0.048 (5)0.056 (5)0.002 (4)0.032 (4)0.012 (4)
C60.056 (5)0.038 (4)0.063 (5)0.008 (4)0.035 (4)0.001 (3)
C70.038 (4)0.040 (4)0.044 (4)0.001 (4)0.008 (3)0.007 (3)
C110.052 (5)0.036 (4)0.053 (4)0.006 (3)0.016 (4)0.009 (3)
C120.053 (4)0.066 (4)0.035 (3)0.003 (3)0.008 (3)0.004 (3)
C130.054 (4)0.073 (5)0.042 (3)0.006 (4)0.017 (3)0.000 (3)
C140.031 (4)0.051 (4)0.052 (4)0.010 (3)0.011 (3)0.015 (3)
C150.046 (4)0.043 (4)0.042 (3)0.000 (3)0.001 (3)0.005 (3)
C160.054 (4)0.040 (3)0.043 (3)0.003 (3)0.019 (3)0.002 (3)
C180.059 (5)0.123 (7)0.100 (6)0.011 (5)0.046 (5)0.047 (6)
O280.052 (3)0.045 (3)0.060 (3)0.005 (3)0.015 (3)0.014 (2)
O290.049 (3)0.043 (3)0.053 (3)0.002 (3)0.009 (3)0.011 (2)
O370.047 (3)0.071 (4)0.090 (4)0.005 (3)0.022 (3)0.007 (3)
N300.053 (4)0.042 (4)0.066 (4)0.006 (3)0.013 (3)0.016 (3)
C210.060 (5)0.032 (4)0.037 (3)0.002 (4)0.012 (3)0.003 (3)
C220.048 (4)0.029 (4)0.046 (4)0.001 (3)0.004 (4)0.000 (3)
C230.054 (5)0.043 (4)0.062 (5)0.010 (4)0.012 (4)0.012 (3)
C240.079 (7)0.054 (5)0.048 (5)0.017 (5)0.017 (5)0.011 (4)
C250.077 (7)0.050 (5)0.051 (4)0.012 (5)0.021 (5)0.008 (4)
C260.053 (5)0.047 (4)0.045 (4)0.007 (4)0.012 (3)0.000 (3)
C270.055 (5)0.030 (4)0.039 (4)0.008 (4)0.015 (3)0.003 (3)
C310.042 (4)0.049 (4)0.045 (4)0.009 (4)0.008 (3)0.015 (3)
C320.052 (4)0.035 (4)0.088 (5)0.005 (3)0.020 (4)0.007 (3)
C330.071 (5)0.040 (4)0.094 (5)0.011 (4)0.030 (4)0.005 (4)
C340.055 (5)0.046 (5)0.060 (5)0.003 (4)0.017 (4)0.010 (4)
C350.053 (4)0.049 (4)0.058 (4)0.012 (3)0.008 (3)0.004 (3)
C360.058 (4)0.039 (4)0.043 (3)0.006 (3)0.010 (3)0.003 (3)
C380.066 (5)0.092 (7)0.116 (7)0.016 (5)0.047 (5)0.009 (5)
O480.046 (3)0.052 (3)0.061 (3)0.014 (3)0.015 (3)0.021 (2)
O490.051 (3)0.044 (3)0.062 (3)0.011 (3)0.021 (3)0.017 (3)
O570.050 (4)0.063 (4)0.089 (4)0.007 (3)0.021 (3)0.005 (3)
N500.049 (4)0.047 (4)0.086 (5)0.012 (3)0.025 (4)0.020 (4)
C410.038 (4)0.039 (4)0.043 (4)0.009 (3)0.015 (3)0.004 (3)
C420.050 (5)0.035 (4)0.048 (4)0.006 (4)0.020 (4)0.005 (3)
C430.060 (5)0.050 (5)0.042 (4)0.009 (4)0.007 (4)0.011 (3)
C440.072 (6)0.039 (4)0.048 (4)0.002 (4)0.020 (4)0.016 (4)
C450.060 (6)0.048 (5)0.053 (4)0.002 (4)0.027 (4)0.003 (4)
C460.050 (4)0.044 (4)0.052 (4)0.000 (4)0.018 (4)0.001 (3)
C470.042 (4)0.037 (4)0.044 (4)0.001 (3)0.014 (3)0.001 (3)
C510.048 (5)0.035 (4)0.057 (4)0.005 (4)0.019 (4)0.008 (3)
C520.052 (4)0.047 (4)0.096 (6)0.003 (4)0.025 (4)0.002 (4)
C530.052 (4)0.044 (4)0.086 (5)0.003 (3)0.023 (4)0.001 (3)
C540.036 (4)0.048 (4)0.050 (4)0.002 (3)0.012 (3)0.005 (3)
C550.049 (4)0.046 (4)0.058 (4)0.002 (3)0.009 (3)0.010 (3)
C560.056 (4)0.037 (4)0.062 (4)0.005 (3)0.008 (3)0.003 (3)
C580.067 (5)0.081 (6)0.109 (7)0.022 (5)0.024 (5)0.003 (5)
O680.052 (3)0.048 (3)0.055 (3)0.005 (3)0.015 (3)0.010 (2)
O690.045 (3)0.042 (3)0.058 (3)0.003 (3)0.011 (3)0.011 (2)
O770.042 (3)0.079 (4)0.081 (4)0.002 (3)0.019 (3)0.007 (3)
N700.052 (4)0.043 (4)0.076 (4)0.012 (3)0.023 (4)0.027 (3)
C610.053 (5)0.028 (4)0.037 (3)0.003 (3)0.013 (3)0.002 (3)
C620.051 (5)0.025 (4)0.051 (4)0.002 (3)0.012 (4)0.002 (3)
C630.051 (5)0.049 (5)0.063 (5)0.003 (4)0.019 (4)0.010 (4)
C640.063 (6)0.045 (4)0.051 (4)0.012 (4)0.021 (4)0.011 (4)
C650.059 (5)0.049 (4)0.054 (4)0.007 (4)0.021 (4)0.011 (4)
C660.050 (4)0.044 (4)0.044 (4)0.009 (4)0.012 (3)0.004 (3)
C670.051 (5)0.032 (4)0.044 (4)0.009 (4)0.014 (4)0.004 (3)
C710.046 (4)0.049 (4)0.040 (4)0.001 (4)0.009 (3)0.012 (3)
C720.052 (4)0.056 (4)0.051 (4)0.001 (3)0.007 (3)0.008 (3)
C730.053 (4)0.070 (4)0.047 (3)0.008 (4)0.016 (3)0.005 (3)
C740.055 (5)0.041 (4)0.056 (5)0.003 (4)0.011 (4)0.001 (4)
C750.040 (3)0.053 (4)0.046 (3)0.005 (3)0.008 (3)0.003 (3)
C760.054 (4)0.045 (3)0.041 (3)0.005 (3)0.010 (3)0.001 (3)
C780.068 (5)0.109 (7)0.108 (7)0.002 (5)0.046 (5)0.033 (6)
Geometric parameters (Å, º) top
O8—C71.321 (11)C31—C361.411 (10)
O9—C71.226 (10)C32—C331.396 (12)
O17—C141.394 (10)C33—C341.381 (13)
O17—C181.421 (11)C34—C351.380 (10)
O8—H80.820C35—C361.380 (11)
O28—C271.321 (11)C23—H230.930
O29—C271.242 (10)C24—H240.930
O37—C341.348 (12)C25—H250.930
O37—C381.417 (10)C26—H260.930
O28—H280.820C32—H320.930
O48—C471.322 (10)C33—H330.930
O49—C471.229 (10)C35—H350.930
O57—C581.411 (10)C36—H360.930
O57—C541.396 (10)C38—H38B0.960
O48—H480.820C38—H38A0.960
O68—C671.322 (11)C38—H38C0.960
O69—C671.232 (10)C41—C471.459 (10)
O77—C741.343 (11)C41—C421.434 (12)
O77—C781.426 (12)C41—C461.408 (12)
O68—H680.820C42—C431.426 (10)
N10—C21.395 (11)C43—C441.340 (13)
N10—C111.413 (11)C44—C451.393 (14)
N10—H100.860C45—C461.374 (11)
N30—C311.425 (11)C51—C521.394 (10)
N30—C221.371 (11)C51—C561.365 (11)
N30—H300.860C52—C531.399 (11)
N50—C421.368 (11)C53—C541.377 (10)
N50—C511.410 (12)C54—C551.355 (9)
N50—H500.860C55—C561.388 (11)
N70—C621.371 (11)C43—H430.930
N70—C711.410 (11)C44—H440.930
N70—H700.860C45—H450.930
C1—C71.455 (9)C46—H460.930
C1—C61.407 (11)C52—H520.930
C1—C21.442 (12)C53—H530.930
C2—C31.428 (10)C55—H550.930
C3—C41.339 (12)C56—H560.930
C4—C51.375 (13)C58—H58A0.960
C5—C61.364 (11)C58—H58C0.960
C11—C121.434 (10)C58—H58B0.960
C11—C161.338 (10)C61—C661.377 (12)
C12—C131.375 (11)C61—C671.481 (10)
C13—C141.380 (10)C61—C621.392 (12)
C14—C151.362 (10)C62—C631.367 (11)
C15—C161.373 (10)C63—C641.399 (13)
C3—H30.930C64—C651.392 (14)
C4—H40.930C65—C661.361 (11)
C5—H50.930C71—C761.441 (10)
C6—H60.930C71—C721.329 (10)
C12—H120.930C72—C731.386 (11)
C13—H130.930C73—C741.387 (11)
C15—H150.930C74—C751.405 (11)
C16—H160.930C75—C761.390 (11)
C18—H18B0.960C63—H630.930
C18—H18A0.960C64—H640.930
C18—H18C0.960C65—H650.930
C21—C221.396 (12)C66—H660.930
C21—C271.463 (10)C72—H720.930
C21—C261.387 (12)C73—H730.930
C22—C231.389 (11)C75—H750.930
C23—C241.389 (13)C76—H760.930
C24—C251.386 (14)C78—H78A0.960
C25—C261.371 (11)C78—H78B0.960
C31—C321.350 (10)C78—H78C0.960
C14—O17—C18117.8 (6)C34—C35—H35119.1
C7—O8—H8109.5C36—C35—H35119.1
C34—O37—C38118.0 (7)C35—C36—H36120.4
C27—O28—H28109.4C31—C36—H36120.5
C54—O57—C58118.0 (7)O37—C38—H38A109.5
C47—O48—H48109.4O37—C38—H38B109.4
C74—O77—C78116.6 (8)H38A—C38—H38C109.5
C67—O68—H68109.5H38B—C38—H38C109.5
C2—N10—C11127.4 (7)H38A—C38—H38B109.5
C11—N10—H10116.3O37—C38—H38C109.5
C2—N10—H10116.2C42—C41—C46119.9 (7)
C22—N30—C31127.5 (6)C42—C41—C47119.7 (7)
C31—N30—H30116.2C46—C41—C47120.4 (7)
C22—N30—H30116.3C41—C42—C43115.8 (8)
C42—N50—C51125.9 (7)N50—C42—C41122.0 (7)
C51—N50—H50117.0N50—C42—C43122.2 (8)
C42—N50—H50117.0C42—C43—C44122.8 (9)
C62—N70—C71128.5 (6)C43—C44—C45121.2 (7)
C71—N70—H70115.8C44—C45—C46119.0 (9)
C62—N70—H70115.7C41—C46—C45121.2 (8)
C6—C1—C7121.0 (7)O48—C47—C41114.0 (7)
C2—C1—C7120.9 (7)O49—C47—C41125.8 (8)
C2—C1—C6118.1 (6)O48—C47—O49120.2 (7)
N10—C2—C3123.0 (8)C52—C51—C56117.8 (8)
N10—C2—C1119.5 (6)N50—C51—C52122.0 (7)
C1—C2—C3117.4 (7)N50—C51—C56119.3 (6)
C2—C3—C4121.1 (8)C51—C52—C53121.4 (7)
C3—C4—C5121.8 (7)C52—C53—C54118.1 (6)
C4—C5—C6119.9 (9)O57—C54—C55115.6 (7)
C1—C6—C5121.6 (8)C53—C54—C55121.5 (7)
O9—C7—C1125.7 (8)O57—C54—C53122.8 (7)
O8—C7—O9120.4 (7)C54—C55—C56119.6 (7)
O8—C7—C1113.9 (7)C51—C56—C55121.7 (6)
C12—C11—C16118.6 (8)C42—C43—H43118.6
N10—C11—C16126.7 (7)C44—C43—H43118.6
N10—C11—C12114.7 (7)C45—C44—H44119.4
C11—C12—C13119.8 (6)C43—C44—H44119.4
C12—C13—C14119.4 (6)C46—C45—H45120.4
C13—C14—C15120.0 (7)C44—C45—H45120.5
O17—C14—C13123.3 (7)C41—C46—H46119.4
O17—C14—C15116.7 (6)C45—C46—H46119.4
C14—C15—C16121.0 (6)C53—C52—H52119.3
C11—C16—C15121.2 (6)C51—C52—H52119.3
C4—C3—H3119.5C54—C53—H53121.0
C2—C3—H3119.4C52—C53—H53121.0
C5—C4—H4119.1C56—C55—H55120.3
C3—C4—H4119.1C54—C55—H55120.2
C6—C5—H5120.0C55—C56—H56119.2
C4—C5—H5120.1C51—C56—H56119.1
C5—C6—H6119.2H58B—C58—H58C109.5
C1—C6—H6119.2H58A—C58—H58B109.5
C11—C12—H12120.0H58A—C58—H58C109.5
C13—C12—H12120.1O57—C58—H58C109.4
C12—C13—H13120.3O57—C58—H58A109.5
C14—C13—H13120.3O57—C58—H58B109.5
C14—C15—H15119.6C62—C61—C66119.4 (7)
C16—C15—H15119.5C62—C61—C67123.0 (8)
C11—C16—H16119.4C66—C61—C67117.6 (8)
C15—C16—H16119.4N70—C62—C63121.2 (8)
O17—C18—H18A109.5N70—C62—C61119.8 (6)
H18A—C18—H18C109.5C61—C62—C63119.0 (8)
O17—C18—H18B109.5C62—C63—C64120.9 (8)
H18A—C18—H18B109.5C63—C64—C65119.9 (7)
H18B—C18—H18C109.5C64—C65—C66118.0 (9)
O17—C18—H18C109.4C61—C66—C65122.8 (8)
C22—C21—C26118.6 (7)O69—C67—C61123.6 (8)
C26—C21—C27117.7 (8)O68—C67—C61114.2 (7)
C22—C21—C27123.8 (8)O68—C67—O69122.2 (7)
N30—C22—C23120.6 (8)N70—C71—C72122.7 (7)
C21—C22—C23119.6 (8)N70—C71—C76119.2 (7)
N30—C22—C21119.7 (7)C72—C71—C76117.9 (7)
C22—C23—C24120.3 (8)C71—C72—C73123.6 (6)
C23—C24—C25120.5 (8)C72—C73—C74119.8 (6)
C24—C25—C26118.6 (9)O77—C74—C75115.2 (8)
C21—C26—C25122.4 (8)O77—C74—C73126.3 (8)
O28—C27—C21115.5 (7)C73—C74—C75118.5 (8)
O29—C27—C21122.9 (8)C74—C75—C76120.6 (6)
O28—C27—O29121.5 (7)C71—C76—C75119.4 (6)
N30—C31—C36117.2 (6)C62—C63—H63119.5
N30—C31—C32123.7 (7)C64—C63—H63119.6
C32—C31—C36119.1 (7)C63—C64—H64120.0
C31—C32—C33121.5 (7)C65—C64—H64120.0
C32—C33—C34120.0 (7)C64—C65—H65121.1
O37—C34—C35116.4 (8)C66—C65—H65120.9
C33—C34—C35118.5 (9)C61—C66—H66118.6
O37—C34—C33125.0 (8)C65—C66—H66118.6
C34—C35—C36121.7 (7)C71—C72—H72118.2
C31—C36—C35119.1 (6)C73—C72—H72118.2
C22—C23—H23119.8C72—C73—H73120.2
C24—C23—H23119.9C74—C73—H73120.1
C25—C24—H24119.7C74—C75—H75119.8
C23—C24—H24119.8C76—C75—H75119.7
C26—C25—H25120.7C71—C76—H76120.3
C24—C25—H25120.7C75—C76—H76120.3
C25—C26—H26118.8O77—C78—H78A109.5
C21—C26—H26118.8O77—C78—H78B109.5
C33—C32—H32119.3O77—C78—H78C109.6
C31—C32—H32119.3H78A—C78—H78B109.4
C32—C33—H33120.0H78A—C78—H78C109.4
C34—C33—H33120.0H78B—C78—H78C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O8—H8···O69i0.821.802.612 (8)172
N10—H10···O90.861.972.662 (9)137
O28—H28···O49ii0.821.822.644 (8)178
N30—H30···O290.862.052.669 (9)128
O48—H48···O29i0.821.792.608 (8)174
N50—H50···O490.862.032.673 (9)131
O68—H68···O9ii0.821.852.666 (8)176
N70—H70···O690.862.012.673 (9)133
C26—H26···O280.932.312.678 (9)103
C46—H46···O480.932.392.714 (9)100
C66—H66···O680.932.292.662 (9)103
Symmetry codes: (i) x1, y, z1/2; (ii) x+1, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC14H13NO3
Mr243.25
Crystal system, space groupMonoclinic, Pc
Temperature (K)293
a, b, c (Å)12.6506 (6), 10.1894 (5), 19.8565 (12)
β (°) 107.160 (5)
V3)2445.6 (2)
Z8
Radiation typeCu Kα
µ (mm1)0.77
Crystal size (mm)0.50 × 0.22 × 0.08
Data collection
DiffractometerSiemens P4 four-circle
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.699, 0.940
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
5863, 4933, 3152
Rint0.053
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.155, 1.05
No. of reflections4933
No. of parameters658
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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).

Selected geometric parameters (Å, º) top
O8—C71.321 (11)O68—C671.322 (11)
O9—C71.226 (10)O69—C671.232 (10)
O17—C141.394 (10)O77—C741.343 (11)
O17—C181.421 (11)O77—C781.426 (12)
O28—C271.321 (11)N10—C21.395 (11)
O29—C271.242 (10)N10—C111.413 (11)
O37—C341.348 (12)N30—C311.425 (11)
O37—C381.417 (10)N30—C221.371 (11)
O48—C471.322 (10)N50—C421.368 (11)
O49—C471.229 (10)N50—C511.410 (12)
O57—C581.411 (10)N70—C621.371 (11)
O57—C541.396 (10)N70—C711.410 (11)
C14—O17—C18117.8 (6)N30—C31—C36117.2 (6)
C34—O37—C38118.0 (7)N30—C31—C32123.7 (7)
C54—O57—C58118.0 (7)O37—C34—C35116.4 (8)
C74—O77—C78116.6 (8)O37—C34—C33125.0 (8)
C2—N10—C11127.4 (7)N50—C42—C41122.0 (7)
C22—N30—C31127.5 (6)N50—C42—C43122.2 (8)
C42—N50—C51125.9 (7)O48—C47—C41114.0 (7)
C62—N70—C71128.5 (6)O49—C47—C41125.8 (8)
N10—C2—C3123.0 (8)O48—C47—O49120.2 (7)
N10—C2—C1119.5 (6)N50—C51—C52122.0 (7)
O9—C7—C1125.7 (8)N50—C51—C56119.3 (6)
O8—C7—O9120.4 (7)O57—C54—C55115.6 (7)
O8—C7—C1113.9 (7)O57—C54—C53122.8 (7)
N10—C11—C16126.7 (7)N70—C62—C63121.2 (8)
N10—C11—C12114.7 (7)N70—C62—C61119.8 (6)
O17—C14—C13123.3 (7)O69—C67—C61123.6 (8)
O17—C14—C15116.7 (6)O68—C67—C61114.2 (7)
N30—C22—C23120.6 (8)O68—C67—O69122.2 (7)
N30—C22—C21119.7 (7)N70—C71—C72122.7 (7)
O28—C27—C21115.5 (7)N70—C71—C76119.2 (7)
O29—C27—C21122.9 (8)O77—C74—C75115.2 (8)
O28—C27—O29121.5 (7)O77—C74—C73126.3 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O8—H8···O69i0.821.802.612 (8)172
N10—H10···O90.861.972.662 (9)137
O28—H28···O49ii0.821.822.644 (8)178
N30—H30···O290.862.052.669 (9)128
O48—H48···O29i0.821.792.608 (8)174
N50—H50···O490.862.032.673 (9)131
O68—H68···O9ii0.821.852.666 (8)176
N70—H70···O690.862.012.673 (9)133
C26—H26···O280.932.312.678 (9)103
C46—H46···O480.932.392.714 (9)100
C66—H66···O680.932.292.662 (9)103
Symmetry codes: (i) x1, y, z1/2; (ii) x+1, y, z+1/2.
 

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