





Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810045046/gk2313sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810045046/gk2313Isup2.hkl |
CCDC reference: 803117
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.115
- Data-to-parameter ratio = 17.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 6 PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 5 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 48
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
To a well stirred solution of 2-hydroxybenzoic acid (1.38 g, 0.01 mol, 1 eq) and SOCl2 (0.87 ml, 1.42 g, 0.012 mol, 1.2 eq) in dry CHCl3, 3-chloroaniline (1.05 ml, 1.27 g, 0.01 mol, 1 eq) and Et3N (2.08 ml, 1.5 g, 0.015 mol, 1.5 eq) was added slowly at room temperature, followed by reflux for three hours. After the completion of the reaction, the reaction mixture was cooled to room temperature, neutralized with aqueous NaHCO3 (10%) and the title compound was obtained as a white solid. The crude solid was filtered off and recrystallized from CHCl3 to afford white prisms.
The coordinates of H atoms of the amide and hydroxy groups were refined whereas the remaining H atoms were positioned geometrically with C–H = 0.93 Å and were included in the refinement in the riding model approximation. The isotropic displacement parameters of H atoms were set as Uiso(H) = 1.2Ueq(C, N, O).
Benzoxazepines are known for their mild tranquilizing activities. Different synthetic derivatives of benzoxazepine are potential biological candidates and exhibit a wide range of biological activities, e.g., anti-inflammatory activity (Pae et al., 2004), anti-depressant and anti-psychotic activity (Coupet et al., 1979). The title compound (I, Fig. 1) has been prepared as a precursor for the asymmetric synthesis of benzoxazepines.
We have reported the crystal structures of (II) i.e., N-(4-chlorophenyl) -2-hydroxybenzamide (Raza et al., 2010a), (III) 2-hydroxy-5-nitro -N-phenylbenzamide (Raza et al., 2010b) and (IV) 2-hydroxy-3-nitro-N-phenylbenzamide (Raza et al., 2009) which are related to the title compound. The title compound differs from (II) due to attachment of chloro group at position-3 instead of position-4.
In (I), the phenyl rings A (C1–C6) of 2-hydroxyphenyl is planar with r. m. s. deviation of 0.012 Å and the O-atom of hydroxy group [O1] is at a distance of -0.078 (2) Å. Similary the phenyl ring B (C8—C13) of 3-chloroanilinic group is planar with r. m. s. deviation of 0.004 Å and the chloro group [CL1] is at a distance of -0.076 (2) Å. The dihedral angle between A/B is 5.57 (9)°. There exist intramolecular H-bonds of N—H···O and C—H···O types (Table 1, Fig. 1) completing S(6) ring motifs (Bernstein et al., 1995). The molecules are arranged to form one dimensional polymeric chains extending along the crystallographic b axis due to intermolecular H-bonds of O—H···O type (Table 1, Fig. 2). The C—H···π interactions (Table 1) and π–π interactions [the centroids of both aromatic rings at a distance of 3.934 (10) Å (symmetry: 1 - x, - y, 1 - z)] play an important role in stabilization of the crystal.
For pharmacological background to this work, see: Coupet et al. (1979); Pae et al. (2004). For related structures, see: Raza et al. (2009, 2010a,b). For graph-set notation, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
C13H10ClNO2 | F(000) = 512 |
Mr = 247.67 | Dx = 1.448 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1827 reflections |
a = 13.4638 (5) Å | θ = 1.5–28.5° |
b = 11.9019 (4) Å | µ = 0.32 mm−1 |
c = 7.1764 (2) Å | T = 296 K |
β = 98.808 (2)° | Prism, white |
V = 1136.42 (7) Å3 | 0.24 × 0.16 × 0.15 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 2806 independent reflections |
Radiation source: fine-focus sealed tube | 1827 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 7.5 pixels mm-1 | θmax = 28.5°, θmin = 2.3° |
ω scans | h = −17→17 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −15→15 |
Tmin = 0.982, Tmax = 0.987 | l = −5→9 |
10332 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0498P)2 + 0.1662P] where P = (Fo2 + 2Fc2)/3 |
2806 reflections | (Δ/σ)max = 0.001 |
161 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
C13H10ClNO2 | V = 1136.42 (7) Å3 |
Mr = 247.67 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.4638 (5) Å | µ = 0.32 mm−1 |
b = 11.9019 (4) Å | T = 296 K |
c = 7.1764 (2) Å | 0.24 × 0.16 × 0.15 mm |
β = 98.808 (2)° |
Bruker Kappa APEXII CCD diffractometer | 2806 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 1827 reflections with I > 2σ(I) |
Tmin = 0.982, Tmax = 0.987 | Rint = 0.033 |
10332 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.115 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.25 e Å−3 |
2806 reflections | Δρmin = −0.34 e Å−3 |
161 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su'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 |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.95784 (4) | −0.09691 (5) | 0.80925 (10) | 0.0858 (3) | |
O1 | 0.49322 (9) | −0.04858 (10) | 0.79519 (19) | 0.0502 (3) | |
H1 | 0.4719 (16) | −0.1099 (18) | 0.840 (3) | 0.071 (7)* | |
O2 | 0.55912 (9) | 0.26044 (9) | 0.57224 (17) | 0.0480 (3) | |
N1 | 0.61841 (11) | 0.09050 (11) | 0.6738 (2) | 0.0414 (3) | |
H1A | 0.5995 (13) | 0.0264 (16) | 0.714 (2) | 0.050* | |
C1 | 0.44202 (12) | 0.13109 (13) | 0.6707 (2) | 0.0365 (4) | |
C2 | 0.41952 (12) | 0.02934 (13) | 0.7532 (2) | 0.0389 (4) | |
C3 | 0.32279 (13) | 0.00851 (15) | 0.7912 (2) | 0.0461 (4) | |
H3 | 0.3090 | −0.0579 | 0.8505 | 0.055* | |
C4 | 0.24770 (14) | 0.08575 (16) | 0.7414 (3) | 0.0522 (5) | |
H4 | 0.1834 | 0.0714 | 0.7677 | 0.063* | |
C5 | 0.26700 (13) | 0.18469 (15) | 0.6526 (3) | 0.0536 (5) | |
H5 | 0.2155 | 0.2358 | 0.6160 | 0.064* | |
C6 | 0.36320 (13) | 0.20707 (14) | 0.6187 (2) | 0.0452 (4) | |
H6 | 0.3760 | 0.2741 | 0.5600 | 0.054* | |
C7 | 0.54346 (12) | 0.16594 (13) | 0.6345 (2) | 0.0367 (4) | |
C8 | 0.72051 (13) | 0.10029 (13) | 0.6548 (2) | 0.0390 (4) | |
C9 | 0.78234 (13) | 0.01425 (15) | 0.7347 (2) | 0.0456 (4) | |
H9 | 0.7562 | −0.0433 | 0.8002 | 0.055* | |
C10 | 0.88287 (14) | 0.01472 (16) | 0.7165 (3) | 0.0522 (5) | |
C11 | 0.92390 (15) | 0.09982 (18) | 0.6235 (3) | 0.0589 (5) | |
H11 | 0.9920 | 0.1001 | 0.6141 | 0.071* | |
C12 | 0.86155 (14) | 0.18490 (16) | 0.5443 (3) | 0.0547 (5) | |
H12 | 0.8883 | 0.2427 | 0.4802 | 0.066* | |
C13 | 0.76052 (13) | 0.18621 (14) | 0.5579 (2) | 0.0467 (4) | |
H13 | 0.7196 | 0.2439 | 0.5030 | 0.056* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0602 (4) | 0.0860 (5) | 0.1122 (5) | 0.0296 (3) | 0.0165 (3) | 0.0241 (4) |
O1 | 0.0486 (7) | 0.0319 (7) | 0.0723 (9) | 0.0043 (6) | 0.0163 (6) | 0.0114 (6) |
O2 | 0.0565 (8) | 0.0283 (6) | 0.0615 (8) | 0.0036 (5) | 0.0166 (6) | 0.0055 (5) |
N1 | 0.0423 (8) | 0.0303 (7) | 0.0532 (9) | 0.0016 (6) | 0.0123 (6) | 0.0043 (6) |
C1 | 0.0434 (9) | 0.0304 (8) | 0.0350 (8) | 0.0017 (7) | 0.0033 (7) | −0.0061 (6) |
C2 | 0.0437 (9) | 0.0322 (8) | 0.0402 (9) | 0.0015 (7) | 0.0044 (7) | −0.0051 (7) |
C3 | 0.0465 (10) | 0.0411 (10) | 0.0506 (10) | −0.0058 (8) | 0.0076 (8) | −0.0008 (8) |
C4 | 0.0391 (10) | 0.0557 (12) | 0.0611 (11) | −0.0035 (8) | 0.0056 (8) | −0.0098 (9) |
C5 | 0.0431 (10) | 0.0474 (11) | 0.0666 (12) | 0.0093 (8) | −0.0040 (9) | −0.0048 (9) |
C6 | 0.0463 (10) | 0.0362 (9) | 0.0507 (10) | 0.0044 (8) | −0.0010 (8) | −0.0024 (7) |
C7 | 0.0456 (9) | 0.0273 (8) | 0.0370 (8) | 0.0027 (7) | 0.0062 (7) | −0.0049 (6) |
C8 | 0.0426 (9) | 0.0351 (9) | 0.0404 (9) | 0.0006 (7) | 0.0095 (7) | −0.0055 (7) |
C9 | 0.0472 (10) | 0.0415 (10) | 0.0495 (10) | 0.0040 (8) | 0.0122 (8) | 0.0022 (8) |
C10 | 0.0467 (10) | 0.0532 (11) | 0.0563 (11) | 0.0094 (9) | 0.0065 (8) | −0.0018 (9) |
C11 | 0.0426 (10) | 0.0674 (13) | 0.0679 (13) | −0.0031 (10) | 0.0125 (9) | −0.0082 (10) |
C12 | 0.0542 (11) | 0.0509 (11) | 0.0617 (12) | −0.0099 (9) | 0.0174 (9) | −0.0004 (9) |
C13 | 0.0507 (10) | 0.0394 (10) | 0.0508 (10) | −0.0028 (8) | 0.0105 (8) | 0.0000 (8) |
Cl1—C10 | 1.7381 (19) | C4—H4 | 0.9300 |
O1—C2 | 1.3579 (19) | C5—C6 | 1.380 (2) |
O1—H1 | 0.87 (2) | C5—H5 | 0.9300 |
O2—C7 | 1.2400 (19) | C6—H6 | 0.9300 |
N1—C7 | 1.348 (2) | C8—C9 | 1.387 (2) |
N1—C8 | 1.407 (2) | C8—C13 | 1.391 (2) |
N1—H1A | 0.866 (18) | C9—C10 | 1.380 (2) |
C1—C6 | 1.401 (2) | C9—H9 | 0.9300 |
C1—C2 | 1.401 (2) | C10—C11 | 1.375 (3) |
C1—C7 | 1.488 (2) | C11—C12 | 1.381 (3) |
C2—C3 | 1.393 (2) | C11—H11 | 0.9300 |
C3—C4 | 1.373 (2) | C12—C13 | 1.379 (2) |
C3—H3 | 0.9300 | C12—H12 | 0.9300 |
C4—C5 | 1.383 (3) | C13—H13 | 0.9300 |
C2—O1—H1 | 112.7 (14) | O2—C7—N1 | 121.10 (15) |
C7—N1—C8 | 129.47 (14) | O2—C7—C1 | 121.81 (14) |
C7—N1—H1A | 114.0 (12) | N1—C7—C1 | 117.09 (14) |
C8—N1—H1A | 116.5 (12) | C9—C8—C13 | 119.72 (16) |
C6—C1—C2 | 117.81 (15) | C9—C8—N1 | 115.60 (14) |
C6—C1—C7 | 116.86 (14) | C13—C8—N1 | 124.65 (15) |
C2—C1—C7 | 125.34 (14) | C10—C9—C8 | 119.55 (17) |
O1—C2—C3 | 120.55 (15) | C10—C9—H9 | 120.2 |
O1—C2—C1 | 119.08 (15) | C8—C9—H9 | 120.2 |
C3—C2—C1 | 120.37 (15) | C11—C10—C9 | 121.47 (18) |
C4—C3—C2 | 120.22 (16) | C11—C10—Cl1 | 119.74 (15) |
C4—C3—H3 | 119.9 | C9—C10—Cl1 | 118.78 (15) |
C2—C3—H3 | 119.9 | C10—C11—C12 | 118.42 (18) |
C3—C4—C5 | 120.50 (17) | C10—C11—H11 | 120.8 |
C3—C4—H4 | 119.7 | C12—C11—H11 | 120.8 |
C5—C4—H4 | 119.7 | C13—C12—C11 | 121.54 (18) |
C6—C5—C4 | 119.56 (17) | C13—C12—H12 | 119.2 |
C6—C5—H5 | 120.2 | C11—C12—H12 | 119.2 |
C4—C5—H5 | 120.2 | C12—C13—C8 | 119.29 (17) |
C5—C6—C1 | 121.45 (16) | C12—C13—H13 | 120.4 |
C5—C6—H6 | 119.3 | C8—C13—H13 | 120.4 |
C1—C6—H6 | 119.3 | ||
C8—N1—C7—O2 | −0.4 (3) | C1—C2—C3—C4 | 2.6 (3) |
C8—N1—C7—C1 | −179.66 (16) | C2—C3—C4—C5 | 0.2 (3) |
C7—N1—C8—C9 | 170.31 (17) | C3—C4—C5—C6 | −1.8 (3) |
C7—N1—C8—C13 | −11.9 (3) | C4—C5—C6—C1 | 0.7 (3) |
C6—C1—C2—O1 | 176.28 (15) | N1—C8—C9—C10 | 177.43 (18) |
C6—C1—C2—C3 | −3.6 (2) | C13—C8—C9—C10 | −0.4 (3) |
C7—C1—C2—O1 | −4.1 (2) | N1—C8—C13—C12 | −178.15 (19) |
C7—C1—C2—C3 | 176.04 (16) | C9—C8—C13—C12 | −0.5 (3) |
C2—C1—C6—C5 | 2.0 (3) | C8—C9—C10—Cl1 | −177.25 (16) |
C7—C1—C6—C5 | −177.67 (17) | C8—C9—C10—C11 | 1.4 (3) |
C2—C1—C7—O2 | −175.16 (15) | Cl1—C10—C11—C12 | 177.29 (17) |
C2—C1—C7—N1 | 4.1 (2) | C9—C10—C11—C12 | −1.3 (3) |
C6—C1—C7—O2 | 4.5 (2) | C10—C11—C12—C13 | 0.4 (3) |
C6—C1—C7—N1 | −176.25 (15) | C11—C12—C13—C8 | 0.5 (3) |
O1—C2—C3—C4 | −177.32 (17) |
Cg1 is the centroid of the C1–C6 benzene ring |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.88 (2) | 1.73 (2) | 2.6016 (18) | 173 (2) |
N1—H1A···O1 | 0.88 (2) | 1.85 (2) | 2.606 (2) | 143.4 (18) |
C13—H13···O2 | 0.93 | 2.30 | 2.869 (2) | 119 |
C6—H6···Cg1ii | 0.93 | 2.89 | 3.675 (2) | 143 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x, −y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C13H10ClNO2 |
Mr | 247.67 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 13.4638 (5), 11.9019 (4), 7.1764 (2) |
β (°) | 98.808 (2) |
V (Å3) | 1136.42 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.32 |
Crystal size (mm) | 0.24 × 0.16 × 0.15 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.982, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10332, 2806, 1827 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.670 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.115, 1.03 |
No. of reflections | 2806 |
No. of parameters | 161 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.25, −0.34 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).
Cg1 is the centroid of the C1–C6 benzene ring |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.88 (2) | 1.73 (2) | 2.6016 (18) | 173 (2) |
N1—H1A···O1 | 0.88 (2) | 1.85 (2) | 2.606 (2) | 143.4 (18) |
C13—H13···O2 | 0.93 | 2.30 | 2.869 (2) | 119 |
C6—H6···Cg1ii | 0.93 | 2.89 | 3.675 (2) | 143 |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x, −y+1/2, z−1/2. |
Benzoxazepines are known for their mild tranquilizing activities. Different synthetic derivatives of benzoxazepine are potential biological candidates and exhibit a wide range of biological activities, e.g., anti-inflammatory activity (Pae et al., 2004), anti-depressant and anti-psychotic activity (Coupet et al., 1979). The title compound (I, Fig. 1) has been prepared as a precursor for the asymmetric synthesis of benzoxazepines.
We have reported the crystal structures of (II) i.e., N-(4-chlorophenyl) -2-hydroxybenzamide (Raza et al., 2010a), (III) 2-hydroxy-5-nitro -N-phenylbenzamide (Raza et al., 2010b) and (IV) 2-hydroxy-3-nitro-N-phenylbenzamide (Raza et al., 2009) which are related to the title compound. The title compound differs from (II) due to attachment of chloro group at position-3 instead of position-4.
In (I), the phenyl rings A (C1–C6) of 2-hydroxyphenyl is planar with r. m. s. deviation of 0.012 Å and the O-atom of hydroxy group [O1] is at a distance of -0.078 (2) Å. Similary the phenyl ring B (C8—C13) of 3-chloroanilinic group is planar with r. m. s. deviation of 0.004 Å and the chloro group [CL1] is at a distance of -0.076 (2) Å. The dihedral angle between A/B is 5.57 (9)°. There exist intramolecular H-bonds of N—H···O and C—H···O types (Table 1, Fig. 1) completing S(6) ring motifs (Bernstein et al., 1995). The molecules are arranged to form one dimensional polymeric chains extending along the crystallographic b axis due to intermolecular H-bonds of O—H···O type (Table 1, Fig. 2). The C—H···π interactions (Table 1) and π–π interactions [the centroids of both aromatic rings at a distance of 3.934 (10) Å (symmetry: 1 - x, - y, 1 - z)] play an important role in stabilization of the crystal.