






Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989015020575/hb7532sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989015020575/hb7532Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989015020575/hb7532Isup3.cml |
CCDC reference: 1434264
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.109
- Data-to-parameter ratio = 17.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT414_ALERT_2_C Short Intra D-H..H-X H1 .. H2 .. 1.96 Ang.
Alert level G PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ... 3 Report PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 251 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 1 ALERT level C = Check. Ensure it is not caused by an omission or oversight 2 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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
The title molecule was synthesized taking 0.100 g (0.812 mmol) of 2-amino-4-methylphenol dissolved in acetonitrile (10 mL), and then was added benzoyl chloride (0.100 mL, 0.860 mmol). The solution was placed under reflux and constant stirring for 3 hours at 150°C. The solid was filtered and recrystallized from methanol. The solvent was evaporated at room temperature and pink crystals were obtained (m.p. 448 (1)K).
All H-atoms were positioned in geometrically idealized positions, C—H = 0.95 Å, and were refined using a riding-model approximation with Uiso(H) constrained to 1.2 times Ueq of the respective parent atom. H1 atom was found from the Fourier maps and its coordinates were refined freely.
The crystal structure determination of N-(2-hydroxy-5-methylphenyl)benzamide (I), is part of a study on phenylbenzamides carried out in our research group, and it was synthesized from the reaction between of 2-amino-4-methylphenol and benzoyl chloride in acetonitrile. Benzanilide systems have a wide range of biological properties such as potassium channel activators (Calderone et al., 2006). Similar compounds to (I) have been reported in the literature: 2-Methyl-N-(m-tolyl)benzamide (II) (Gowda et al., 2008) and N-(3,5-Dimethylphenyl)-4-methylbenzamide (III) (Rodrigues et al., 2011). The molecular structure of (I) is shown in Fig. 1. The central amide moiety, C8—N1-C7(═O1)—C1, is close to planar (r.m.s. deviation for all non-H atoms = 0.0291 Å) and it forms dihedral angles of 5.63 (6)° with the C1-C6 and 10.20 (5)° with the C8-C13 rings respectively. Bond lengths and bond angles in the molecule are in a good agreement with those found in the related compounds (II) and (III). The conformation of the N—H group is syn to the –OH substituent in the benzoyl ring, which results in a short intramolecular N—H···O contact. In the crystal (Fig. 2), molecules are linked by strong O-H···O hydrogen bonds and weak C-H···O intermolecular contacts. Indeed, the O2-H20 at (x,y,z) acts as a hydrogen-bond donor to O1 atom of the carbonyl group at (x+1,+y,+z) and the C6-H6 acts as a hydrogen-bond donor to O2 atom of the hydroxyl group at (x-1,+y,+z). These interactions generate C(7) chains of molecules and R22(7) rings (See Fig. 2), running along [100]. Additionally, the molecules are linked by N-H···O interactions. N1-H1 acts as a hydrogen-bond donor to O2 atom of the hydroxyl group at (-x+1,-y,-z+1), forming inversion dimers (Fig. 3).
For the biological activity of benzanilide derivatives, see Calderone et al. (2006). For related structures, see: Gowda et al. (2008); Rodrigues et al. (2011).
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).
C14H13NO2 | Dx = 1.370 Mg m−3 |
Mr = 227.25 | Melting point: 448(1) K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2263 (3) Å | Cell parameters from 10254 reflections |
b = 21.7442 (7) Å | θ = 3.4–29.4° |
c = 7.4747 (3) Å | µ = 0.09 mm−1 |
β = 110.280 (5)° | T = 123 K |
V = 1101.69 (8) Å3 | Block, pink |
Z = 4 | 0.40 × 0.35 × 0.25 mm |
F(000) = 480 |
Oxford Diffraction Gemini S CCD diffractometer | 2332 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 29.4°, θmin = 3.4° |
ω scans | h = −9→9 |
10254 measured reflections | k = −30→30 |
2795 independent reflections | l = −9→10 |
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: mixed |
wR(F2) = 0.109 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0448P)2 + 0.5141P] where P = (Fo2 + 2Fc2)/3 |
2795 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C14H13NO2 | V = 1101.69 (8) Å3 |
Mr = 227.25 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.2263 (3) Å | µ = 0.09 mm−1 |
b = 21.7442 (7) Å | T = 123 K |
c = 7.4747 (3) Å | 0.40 × 0.35 × 0.25 mm |
β = 110.280 (5)° |
Oxford Diffraction Gemini S CCD diffractometer | 2332 reflections with I > 2σ(I) |
10254 measured reflections | Rint = 0.032 |
2795 independent reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.109 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.33 e Å−3 |
2795 reflections | Δρmin = −0.27 e Å−3 |
163 parameters |
Experimental. The IR spectrum was recorded on a FT—IR SHIMADZU IR-Affinity-1 spectrophotometer. IR (KBr), cm-1, 3395 (amide N-H); 3073 (Hydroxyl O-H), 1643 (amide, C=O); 1593 (C=C). |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
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 | ||
O2 | 0.55117 (13) | 0.05937 (4) | 0.41236 (14) | 0.0204 (2) | |
O1 | −0.14306 (13) | 0.07692 (4) | 0.30232 (14) | 0.0214 (2) | |
N1 | 0.17579 (15) | 0.05132 (5) | 0.36397 (15) | 0.0166 (2) | |
C1 | −0.07846 (17) | −0.02289 (5) | 0.20522 (16) | 0.0153 (2) | |
C2 | 0.05257 (19) | −0.06486 (6) | 0.17363 (18) | 0.0192 (3) | |
H2 | 0.1892 | −0.0554 | 0.2136 | 0.023* | |
C3 | −0.0159 (2) | −0.12053 (6) | 0.08386 (19) | 0.0222 (3) | |
H3 | 0.0743 | −0.1490 | 0.0632 | 0.027* | |
C4 | −0.2145 (2) | −0.13469 (6) | 0.02438 (18) | 0.0217 (3) | |
H4 | −0.2607 | −0.1728 | −0.0371 | 0.026* | |
C5 | −0.34605 (19) | −0.09320 (6) | 0.05467 (19) | 0.0224 (3) | |
H5 | −0.4827 | −0.1028 | 0.0136 | 0.027* | |
C6 | −0.27845 (18) | −0.03785 (6) | 0.14471 (18) | 0.0193 (3) | |
H6 | −0.3693 | −0.0097 | 0.1656 | 0.023* | |
C7 | −0.01844 (17) | 0.03897 (5) | 0.29485 (17) | 0.0150 (2) | |
C8 | 0.26922 (17) | 0.10733 (5) | 0.43855 (17) | 0.0149 (2) | |
C13 | 0.17867 (18) | 0.15716 (6) | 0.48997 (17) | 0.0172 (3) | |
H13 | 0.0430 | 0.1547 | 0.4756 | 0.021* | |
C12 | 0.28408 (19) | 0.21075 (6) | 0.56243 (18) | 0.0186 (3) | |
C11 | 0.48182 (19) | 0.21370 (6) | 0.58174 (18) | 0.0202 (3) | |
H11 | 0.5548 | 0.2501 | 0.6301 | 0.024* | |
C10 | 0.57479 (18) | 0.16395 (6) | 0.53108 (18) | 0.0195 (3) | |
H10 | 0.7104 | 0.1666 | 0.5452 | 0.023* | |
C9 | 0.46985 (17) | 0.11075 (5) | 0.46028 (17) | 0.0157 (2) | |
C14 | 0.1817 (2) | 0.26392 (6) | 0.6182 (2) | 0.0258 (3) | |
H141 | 0.2788 | 0.2956 | 0.6812 | 0.039* | |
H142 | 0.1168 | 0.2495 | 0.7059 | 0.039* | |
H143 | 0.0827 | 0.2813 | 0.5038 | 0.039* | |
H1 | 0.258 (2) | 0.0217 (8) | 0.357 (2) | 0.031 (4)* | |
H20 | 0.658 (3) | 0.0685 (9) | 0.383 (3) | 0.047 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0158 (4) | 0.0173 (4) | 0.0316 (5) | 0.0009 (3) | 0.0126 (4) | −0.0013 (4) |
O1 | 0.0150 (4) | 0.0177 (4) | 0.0333 (5) | 0.0005 (3) | 0.0108 (4) | −0.0022 (4) |
N1 | 0.0129 (5) | 0.0147 (5) | 0.0224 (5) | 0.0010 (4) | 0.0063 (4) | −0.0027 (4) |
C1 | 0.0170 (6) | 0.0148 (5) | 0.0142 (5) | −0.0004 (4) | 0.0056 (4) | 0.0008 (4) |
C2 | 0.0161 (6) | 0.0200 (6) | 0.0210 (6) | 0.0009 (5) | 0.0056 (5) | −0.0008 (5) |
C3 | 0.0235 (7) | 0.0188 (6) | 0.0240 (6) | 0.0027 (5) | 0.0078 (5) | −0.0030 (5) |
C4 | 0.0267 (7) | 0.0172 (6) | 0.0190 (6) | −0.0028 (5) | 0.0051 (5) | −0.0012 (5) |
C5 | 0.0186 (6) | 0.0230 (6) | 0.0238 (6) | −0.0047 (5) | 0.0051 (5) | −0.0013 (5) |
C6 | 0.0162 (6) | 0.0197 (6) | 0.0220 (6) | 0.0008 (5) | 0.0065 (5) | −0.0002 (5) |
C7 | 0.0143 (5) | 0.0156 (6) | 0.0164 (5) | 0.0010 (4) | 0.0069 (4) | 0.0014 (4) |
C8 | 0.0145 (6) | 0.0150 (5) | 0.0146 (5) | −0.0003 (4) | 0.0043 (4) | 0.0009 (4) |
C13 | 0.0161 (6) | 0.0180 (6) | 0.0180 (6) | 0.0012 (4) | 0.0065 (5) | −0.0001 (4) |
C12 | 0.0227 (6) | 0.0155 (6) | 0.0178 (6) | 0.0015 (5) | 0.0073 (5) | 0.0006 (4) |
C11 | 0.0230 (7) | 0.0149 (6) | 0.0222 (6) | −0.0034 (5) | 0.0071 (5) | 0.0006 (5) |
C10 | 0.0152 (6) | 0.0195 (6) | 0.0238 (6) | −0.0019 (5) | 0.0069 (5) | 0.0027 (5) |
C9 | 0.0153 (6) | 0.0156 (5) | 0.0172 (6) | 0.0022 (4) | 0.0070 (5) | 0.0022 (4) |
C14 | 0.0297 (7) | 0.0184 (6) | 0.0308 (7) | 0.0023 (5) | 0.0125 (6) | −0.0044 (5) |
O2—C9 | 1.3667 (14) | C5—H5 | 0.9500 |
O2—H20 | 0.89 (2) | C6—H6 | 0.9500 |
O1—C7 | 1.2369 (14) | C8—C13 | 1.3871 (16) |
N1—C7 | 1.3440 (15) | C8—C9 | 1.4038 (16) |
N1—C8 | 1.4103 (15) | C13—C12 | 1.3949 (17) |
N1—H1 | 0.889 (18) | C13—H13 | 0.9500 |
C1—C2 | 1.3929 (17) | C12—C11 | 1.3870 (18) |
C1—C6 | 1.3949 (17) | C12—C14 | 1.5074 (17) |
C1—C7 | 1.4984 (16) | C11—C10 | 1.3933 (18) |
C2—C3 | 1.3893 (17) | C11—H11 | 0.9500 |
C2—H2 | 0.9500 | C10—C9 | 1.3838 (17) |
C3—C4 | 1.3818 (19) | C10—H10 | 0.9500 |
C3—H3 | 0.9500 | C14—H141 | 0.9800 |
C4—C5 | 1.3849 (19) | C14—H142 | 0.9800 |
C4—H4 | 0.9500 | C14—H143 | 0.9800 |
C5—C6 | 1.3829 (18) | ||
C9—O2—H20 | 111.6 (12) | C13—C8—C9 | 119.61 (11) |
C7—N1—C8 | 128.14 (10) | C13—C8—N1 | 125.23 (11) |
C7—N1—H1 | 117.3 (11) | C9—C8—N1 | 115.16 (10) |
C8—N1—H1 | 114.4 (11) | C8—C13—C12 | 120.90 (11) |
C2—C1—C6 | 118.75 (11) | C8—C13—H13 | 119.5 |
C2—C1—C7 | 123.75 (11) | C12—C13—H13 | 119.5 |
C6—C1—C7 | 117.46 (10) | C11—C12—C13 | 118.90 (11) |
C3—C2—C1 | 120.22 (12) | C11—C12—C14 | 121.51 (12) |
C3—C2—H2 | 119.9 | C13—C12—C14 | 119.59 (11) |
C1—C2—H2 | 119.9 | C12—C11—C10 | 120.82 (11) |
C4—C3—C2 | 120.39 (12) | C12—C11—H11 | 119.6 |
C4—C3—H3 | 119.8 | C10—C11—H11 | 119.6 |
C2—C3—H3 | 119.8 | C9—C10—C11 | 120.07 (11) |
C3—C4—C5 | 119.83 (12) | C9—C10—H10 | 120.0 |
C3—C4—H4 | 120.1 | C11—C10—H10 | 120.0 |
C5—C4—H4 | 120.1 | O2—C9—C10 | 123.73 (11) |
C6—C5—C4 | 119.99 (12) | O2—C9—C8 | 116.55 (10) |
C6—C5—H5 | 120.0 | C10—C9—C8 | 119.71 (11) |
C4—C5—H5 | 120.0 | C12—C14—H141 | 109.5 |
C5—C6—C1 | 120.81 (12) | C12—C14—H142 | 109.5 |
C5—C6—H6 | 119.6 | H141—C14—H142 | 109.5 |
C1—C6—H6 | 119.6 | C12—C14—H143 | 109.5 |
O1—C7—N1 | 121.94 (11) | H141—C14—H143 | 109.5 |
O1—C7—C1 | 121.11 (11) | H142—C14—H143 | 109.5 |
N1—C7—C1 | 116.95 (10) | ||
C6—C1—C2—C3 | −0.16 (18) | C7—N1—C8—C9 | −166.27 (11) |
C7—C1—C2—C3 | −177.86 (11) | C9—C8—C13—C12 | 0.22 (18) |
C1—C2—C3—C4 | 0.27 (19) | N1—C8—C13—C12 | −179.91 (11) |
C2—C3—C4—C5 | −0.10 (19) | C8—C13—C12—C11 | 0.28 (18) |
C3—C4—C5—C6 | −0.2 (2) | C8—C13—C12—C14 | −179.59 (12) |
C4—C5—C6—C1 | 0.3 (2) | C13—C12—C11—C10 | −0.44 (19) |
C2—C1—C6—C5 | −0.12 (18) | C14—C12—C11—C10 | 179.44 (12) |
C7—C1—C6—C5 | 177.72 (11) | C12—C11—C10—C9 | 0.08 (19) |
C8—N1—C7—O1 | −5.48 (19) | C11—C10—C9—O2 | −178.11 (11) |
C8—N1—C7—C1 | 173.71 (10) | C11—C10—C9—C8 | 0.44 (18) |
C2—C1—C7—O1 | 172.66 (12) | C13—C8—C9—O2 | 178.06 (11) |
C6—C1—C7—O1 | −5.06 (17) | N1—C8—C9—O2 | −1.82 (15) |
C2—C1—C7—N1 | −6.54 (17) | C13—C8—C9—C10 | −0.59 (17) |
C6—C1—C7—N1 | 175.74 (11) | N1—C8—C9—C10 | 179.54 (11) |
C7—N1—C8—C13 | 13.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.889 (18) | 2.173 (16) | 2.6153 (15) | 110.0 (13) |
N1—H1···O2i | 0.889 (18) | 2.518 (17) | 3.1928 (14) | 133.1 (14) |
O2—H20···O1ii | 0.89 (2) | 1.75 (2) | 2.6390 (12) | 171.3 (19) |
C6—H6···O2iii | 0.95 | 2.59 | 3.4197 (15) | 146 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1, y, z; (iii) x−1, y, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.889 (18) | 2.173 (16) | 2.6153 (15) | 110.0 (13) |
N1—H1···O2i | 0.889 (18) | 2.518 (17) | 3.1928 (14) | 133.1 (14) |
O2—H20···O1ii | 0.89 (2) | 1.75 (2) | 2.6390 (12) | 171.3 (19) |
C6—H6···O2iii | 0.95 | 2.59 | 3.4197 (15) | 146 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1, y, z; (iii) x−1, y, z. |
The crystal structure determination of N-(2-hydroxy-5-methylphenyl)benzamide (I), is part of a study on phenylbenzamides carried out in our research group, and it was synthesized from the reaction between of 2-amino-4-methylphenol and benzoyl chloride in acetonitrile. Benzanilide systems have a wide range of biological properties such as potassium channel activators (Calderone et al., 2006). Similar compounds to (I) have been reported in the literature: 2-Methyl-N-(m-tolyl)benzamide (II) (Gowda et al., 2008) and N-(3,5-Dimethylphenyl)-4-methylbenzamide (III) (Rodrigues et al., 2011). The molecular structure of (I) is shown in Fig. 1. The central amide moiety, C8—N1-C7(═O1)—C1, is close to planar (r.m.s. deviation for all non-H atoms = 0.0291 Å) and it forms dihedral angles of 5.63 (6)° with the C1-C6 and 10.20 (5)° with the C8-C13 rings respectively. Bond lengths and bond angles in the molecule are in a good agreement with those found in the related compounds (II) and (III). The conformation of the N—H group is syn to the –OH substituent in the benzoyl ring, which results in a short intramolecular N—H···O contact. In the crystal (Fig. 2), molecules are linked by strong O-H···O hydrogen bonds and weak C-H···O intermolecular contacts. Indeed, the O2-H20 at (x,y,z) acts as a hydrogen-bond donor to O1 atom of the carbonyl group at (x+1,+y,+z) and the C6-H6 acts as a hydrogen-bond donor to O2 atom of the hydroxyl group at (x-1,+y,+z). These interactions generate C(7) chains of molecules and R22(7) rings (See Fig. 2), running along [100]. Additionally, the molecules are linked by N-H···O interactions. N1-H1 acts as a hydrogen-bond donor to O2 atom of the hydroxyl group at (-x+1,-y,-z+1), forming inversion dimers (Fig. 3).