Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100013615/da1154sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100013615/da1154Isup2.hkl |
CCDC reference: 158264
During the recrystallization of 2-[(4-carboxyphenyl)amino]benzoic acid (Novoa de Armas et al., 2000) from ethanol–water (1:1), pale-yellow plates of the title compound were obtained.
The H atoms were calculated geometrically and included in the refinement, but were restrained to ride on their parent atoms (O—H = 0.82, N—H = 0.86 and C—H = 0.93 Å). The isotropic displacement parameters of the H atoms were fixed to 1.5Ueq of their parent atoms. The absolute structure was not determined as the Flack (1983) parameter was indeterminate [given as 0.0 (4)] due to the lack of sufficient anomalous scatterers.
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: PLATON (Spek, 1990), PARST (Nardelli, 1983, 1995) and PARSTCIF (Nardelli, 1991).
C8H7NO3 | F(000) = 172 |
Mr = 165.15 | Dx = 1.491 Mg m−3 |
Monoclinic, Pc | Cu Kα radiation, λ = 1.54184 Å |
a = 8.0595 (7) Å | Cell parameters from 58 reflections |
b = 3.8631 (2) Å | θ = 7.5–27.6° |
c = 11.812 (1) Å | µ = 0.98 mm−1 |
β = 90.160 (8)° | T = 293 K |
V = 367.77 (5) Å3 | Plate, pale-yellow |
Z = 2 | 0.48 × 0.36 × 0.06 mm |
Siemens P4 four-circle diffractometer | Rint = 0.080 |
ω/2θ scans | θmax = 69.1° |
Absorption correction: ψ scan (North et al., 1968) | h = −1→9 |
Tmin = 0.609, Tmax = 0.943 | k = −1→4 |
1166 measured reflections | l = −14→14 |
789 independent reflections | 3 standard reflections every 100 reflections |
769 reflections with F2 > 2σ(F2) | intensity decay: 0.0% |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0921P)2 + 0.0348P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.046 | (Δ/σ)max = 0.001 |
wR(F2) = 0.129 | Δρmax = 0.21 e Å−3 |
S = 1.13 | Δρmin = −0.22 e Å−3 |
789 reflections | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin((2θ)]-1/4 |
111 parameters | Extinction coefficient: 0.066 (8) |
C8H7NO3 | V = 367.77 (5) Å3 |
Mr = 165.15 | Z = 2 |
Monoclinic, Pc | Cu Kα radiation |
a = 8.0595 (7) Å | µ = 0.98 mm−1 |
b = 3.8631 (2) Å | T = 293 K |
c = 11.812 (1) Å | 0.48 × 0.36 × 0.06 mm |
β = 90.160 (8)° |
Siemens P4 four-circle diffractometer | 769 reflections with F2 > 2σ(F2) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.080 |
Tmin = 0.609, Tmax = 0.943 | 3 standard reflections every 100 reflections |
1166 measured reflections | intensity decay: 0.0% |
789 independent reflections |
R[F2 > 2σ(F2)] = 0.046 | 111 parameters |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.13 | Δρmax = 0.21 e Å−3 |
789 reflections | Δρmin = −0.22 e Å−3 |
x | y | z | Uiso*/Ueq | ||
C1 | −0.2422 (4) | 0.1414 (8) | 0.9069 (3) | 0.0292 (8)* | |
O11 | −0.0396 (3) | 0.1018 (7) | 1.0496 (2) | 0.0490 (8)* | |
C11 | −0.0762 (3) | 0.0236 (8) | 0.9427 (2) | 0.0317 (8)* | |
O12 | 0.0174 (3) | −0.1352 (6) | 0.8820 (2) | 0.0455 (7)* | |
C2 | −0.2933 (3) | 0.0814 (9) | 0.7959 (3) | 0.0309 (9)* | |
C3 | −0.4501 (4) | 0.1755 (9) | 0.7587 (3) | 0.0332 (8)* | |
O4 | −0.7670 (3) | 0.1527 (6) | 0.6374 (2) | 0.0447 (7)* | |
N4 | −0.7195 (3) | 0.4428 (7) | 0.8037 (2) | 0.0345 (8)* | |
C4 | −0.5580 (4) | 0.3352 (7) | 0.8342 (3) | 0.0284 (9)* | |
C41 | −0.8105 (4) | 0.3455 (9) | 0.7144 (3) | 0.036 (1)* | |
C5 | −0.5078 (4) | 0.4029 (8) | 0.9450 (2) | 0.0333 (9)* | |
C6 | −0.3508 (4) | 0.3066 (9) | 0.9804 (2) | 0.0325 (9)* | |
H11 | 0.04078 | −0.01225 | 1.07031 | 0.022 (1)* | |
H2 | −0.22056 | −0.02422 | 0.74558 | 0.025 (2)* | |
H3 | −0.4828 | 0.1327 | 0.6844 | 0.045* | |
H4 | −0.76522 | 0.59015 | 0.84833 | 0.030 (2)* | |
H41 | −0.9179 | 0.4328 | 0.7102 | 0.042* | |
H5 | −0.57975 | 0.51235 | 0.99498 | 0.029 (1)* | |
H6 | −0.3174 | 0.3530 | 1.0543 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O4 | 0.0323 (12) | 0.0586 (15) | 0.0431 (11) | −0.0025 (11) | −0.0128 (10) | −0.0065 (11) |
O11 | 0.0379 (13) | 0.0708 (17) | 0.0383 (11) | 0.0174 (13) | −0.0154 (11) | −0.0042 (11) |
O12 | 0.0298 (11) | 0.0614 (15) | 0.0453 (12) | 0.0136 (11) | −0.0045 (10) | −0.0084 (11) |
N4 | 0.0256 (13) | 0.0341 (13) | 0.0438 (15) | 0.0050 (11) | −0.0061 (11) | −0.0027 (11) |
C1 | 0.0243 (15) | 0.0307 (13) | 0.0326 (14) | −0.0008 (12) | −0.0049 (13) | −0.0001 (12) |
C2 | 0.0250 (16) | 0.0367 (16) | 0.0311 (14) | 0.0021 (13) | −0.0050 (12) | −0.0019 (13) |
C3 | 0.0308 (15) | 0.0383 (16) | 0.0304 (13) | 0.0015 (14) | −0.0058 (13) | −0.0040 (12) |
C4 | 0.0221 (14) | 0.0264 (13) | 0.0367 (15) | 0.0009 (13) | −0.0077 (12) | 0.0026 (13) |
C5 | 0.0302 (15) | 0.0378 (16) | 0.0319 (15) | 0.0047 (13) | −0.0020 (13) | −0.0056 (12) |
C6 | 0.0285 (14) | 0.0387 (16) | 0.0302 (13) | 0.0036 (14) | −0.0069 (12) | −0.0039 (12) |
C11 | 0.0252 (13) | 0.0343 (14) | 0.0355 (15) | 0.0014 (13) | −0.0095 (12) | 0.0015 (13) |
C41 | 0.0251 (16) | 0.0421 (17) | 0.0414 (16) | −0.0016 (13) | −0.0071 (13) | 0.0056 (13) |
C1—C11 | 1.474 (4) | O4—C41 | 1.227 (4) |
C1—C2 | 1.393 (4) | N4—H4 | 0.860 |
C1—C6 | 1.389 (4) | N4—C4 | 1.412 (4) |
O11—H11 | 0.820 | N4—C41 | 1.337 (4) |
O11—C11 | 1.331 (4) | C4—C5 | 1.394 (4) |
C11—O12 | 1.209 (4) | C41—H41 | 0.930 |
C2—H2 | 0.930 | C5—H5 | 0.930 |
C2—C3 | 1.385 (4) | C5—C6 | 1.383 (4) |
C3—H3 | 0.930 | C6—H6 | 0.930 |
C3—C4 | 1.391 (4) | ||
C11—C1—C2 | 119.0 (3) | H4—N4—C41 | 115.8 |
C11—C1—C6 | 122.4 (3) | C4—N4—C41 | 128.5 (3) |
C2—C1—C6 | 118.7 (3) | C3—C4—N4 | 123.0 (3) |
H11—O11—C11 | 109.5 | C3—C4—C5 | 120.3 (3) |
C1—C11—O11 | 113.6 (3) | N4—C4—C5 | 116.7 (3) |
C1—C11—O12 | 123.6 (3) | O4—C41—N4 | 126.7 (3) |
O11—C11—O12 | 122.8 (3) | O4—C41—H41 | 116.7 |
C1—C2—H2 | 119.3 | N4—C41—H41 | 116.7 |
C1—C2—C3 | 121.5 (3) | C4—C5—H5 | 120.1 |
H2—C2—C3 | 119.3 | C4—C5—C6 | 119.7 (3) |
C2—C3—H3 | 120.5 | H5—C5—C6 | 120.1 |
C2—C3—C4 | 118.9 (3) | C1—C6—C5 | 120.8 (3) |
H3—C3—C4 | 120.5 | C1—C6—H6 | 119.6 |
H4—N4—C4 | 115.8 | C5—C6—H6 | 119.6 |
C2—C1—C11—O11 | 178.6 (3) | C2—C3—C4—C5 | 0.8 (4) |
C2—C1—C11—O12 | −2.8 (5) | H3—C3—C4—N4 | −0.5 |
C6—C1—C11—O11 | −2.2 (4) | H3—C3—C4—C5 | −179.2 |
C6—C1—C11—O12 | 176.3 (3) | H4—N4—C4—C3 | −162.4 |
C11—C1—C2—H2 | −2.3 | H4—N4—C4—C5 | 16.4 |
C11—C1—C2—C3 | 177.7 (3) | C41—N4—C4—C3 | 17.6 (5) |
C6—C1—C2—H2 | 178.5 | C41—N4—C4—C5 | −163.6 (3) |
C6—C1—C2—C3 | −1.5 (5) | H4—N4—C41—O4 | 176.1 |
C11—C1—C6—C5 | −177.7 (3) | H4—N4—C41—H41 | −3.9 |
C11—C1—C6—H6 | 2.3 | C4—N4—C41—O4 | −3.9 (5) |
C2—C1—C6—C5 | 1.4 (5) | C4—N4—C41—H41 | 176.1 |
C2—C1—C6—H6 | −178.6 | C3—C4—C5—H5 | 179.2 |
H11—O11—C11—C1 | 164.8 | C3—C4—C5—C6 | −0.8 (4) |
H11—O11—C11—O12 | −13.8 | N4—C4—C5—H5 | 0.4 |
C1—C2—C3—H3 | −179.6 | N4—C4—C5—C6 | −179.6 (3) |
C1—C2—C3—C4 | 0.4 (5) | C4—C5—C6—C1 | −0.3 (5) |
H2—C2—C3—H3 | 0.4 | C4—C5—C6—H6 | 179.7 |
H2—C2—C3—C4 | −179.6 | H5—C5—C6—C1 | 179.7 |
C2—C3—C4—N4 | 179.5 (3) | H5—C5—C6—H6 | −0.3 |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O12i | 0.86 | 2.09 | 2.832 (3) | 145 |
O11—H11···O4ii | 0.82 | 1.82 | 2.618 (3) | 164 |
C3—H3···O4 | 0.93 | 2.36 | 2.926 (4) | 119 |
Symmetry codes: (i) x−1, y+1, z; (ii) x+1, −y, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C8H7NO3 |
Mr | 165.15 |
Crystal system, space group | Monoclinic, Pc |
Temperature (K) | 293 |
a, b, c (Å) | 8.0595 (7), 3.8631 (2), 11.812 (1) |
β (°) | 90.160 (8) |
V (Å3) | 367.77 (5) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 0.98 |
Crystal size (mm) | 0.48 × 0.36 × 0.06 |
Data collection | |
Diffractometer | Siemens P4 four-circle diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.609, 0.943 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 1166, 789, 769 |
Rint | 0.080 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.129, 1.13 |
No. of reflections | 789 |
No. of parameters | 111 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.22 |
Computer programs: XSCANS (Siemens, 1996), XSCANS, SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), DIAMOND (Bergerhoff, 1996), PLATON (Spek, 1990), PARST (Nardelli, 1983, 1995) and PARSTCIF (Nardelli, 1991).
O11—C11 | 1.331 (4) | N4—C4 | 1.412 (4) |
C11—O12 | 1.209 (4) | N4—C41 | 1.337 (4) |
O4—C41 | 1.227 (4) | ||
C1—C11—O11 | 113.6 (3) | C3—C4—N4 | 123.0 (3) |
C1—C11—O12 | 123.6 (3) | N4—C4—C5 | 116.7 (3) |
O11—C11—O12 | 122.8 (3) | O4—C41—N4 | 126.7 (3) |
C4—N4—C41 | 128.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O12i | 0.86 | 2.09 | 2.832 (3) | 145 |
O11—H11···O4ii | 0.82 | 1.82 | 2.618 (3) | 164 |
Symmetry codes: (i) x−1, y+1, z; (ii) x+1, −y, z+1/2. |
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The title compound, (I), is an aromatic amide obtained in the final stages in the synthesis of 2-[(4-carboxyphenyl)amino]benzoic acid (Novoa de Armas et al., 2000), which is used as an intermediate in the synthesis of acridones. Crystals of (I) were isolated as pale-yellow plates, possibly formed as a colateral by-product in the reaction of 2-chlorobenzoic acid with 4-aminobenzoic acid in the presence of K2CO3, dimethylformamide and copper powder. In previous work on N-aromatic amides, the crystal structures of the amides have been classified into three types according to their scheme of N—H···O═C hydrogen bonds, namely 21, glide and translation (Haisa et al., 1980). The hydrogen-bond pattern in the present structure may be used to corroborate previous works in the systematization of crystal structures of aromatic compounds.
The bond lengths and angles in (I) are similar to those reported for p-amidoperbenzoic acids (Feeder & Jones, 1996) and N-aromatic amides (Kashino et al., 1986). In the crystal, nearly flat molecules lie almost parallel to (010) and extend approximately along a. The dihedral angle between the least-square planes involving the benzene ring (A) and the amide group (B) is 3.3 (1)°. The dihedral angle between the least-square planes involving A and the formyl group (C) is 15.0 (1)° and between planes B and C is 12.9 (1)°. The formyl group is out of the plane formed by A and B. An extensive hydrogen-bond network is formed within the crystal. Hydrogen bonds from the acid proton to the amido carbonyl O atom (O11···O4) are formed by a combination of a c glide and a translation in a. The imido proton is hydrogen bonded to the acid carbonyl O12 atom between molecules related by a and b translations (Fig. 2a). The hydrogen-bond motif forming this two-dimensional network is similar to those observed in p-amidoperbenzoic acids (Feeder & Jones, 1996). An N4—H4···O12 intermolecular hydrogen-bond connects translated molecules into a one-dimensional infinite chain running parallel to the [110] and [110] directions, respectively. The chains are cross-linked by O11—H12···O4 hydrogen bonds, resulting in a three-dimensional network (Fig. 2 b). The hydrogen-bond motifs in the crystal structure can be described using Etter's graph-set notation (Etter et al., 1990) as a first-order network C(10) and a second-order network of the type C22(8) C(10), obtained using the RPLUTO program implemented in a recent version of the Cambridge Structural Database (CSD release of April 2000; Allen & Kennard, 1993).