The conformation of the C=O bond in the structure of the title compound, C
14H
13NO, is
anti to the
meta-methyl substituent in the benzoyl ring. The conformations of the N—H and C=O bonds in the amide group are also
anti to each other. The asymmetric unit of the structure contains two molecules. The bond parameters are similar to those in
N-(phenyl)benzamide, 2-methyl-
N-(phenyl)benzamide and other benzanilides. The amide group –NHCO– forms dihedral angles of 20.97 (34) and 45.65 (19)° with the benzoyl rings, and 41.54 (25) and 31.87 (29)° with the aniline rings, in the two independent molecules. The benzoyl and aniline rings adopt dihedral angles of 22.17 (18) and 75.86 (12)° in the two independent molecules. In the crystal structure, molecules are linked into chains by intermolecular N—H

O hydrogen bonds.
Supporting information
CCDC reference: 684564
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean
(C-C) = 0.006 Å
- R factor = 0.082
- wR factor = 0.241
- Data-to-parameter ratio = 13.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.20
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.24
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6
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
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
The title compound was prepared according to the literature method (Gowda et
al., 2003). The purity of the compound was checked by determining
its
melting point. It was characterized by recording its infrared and NMR spectra.
Single crystals of the title compound were obtained from an ethanolic solution
and used for X-ray diffraction studies at room temperature.
The NH atom was located in difference map with N—H = 0.86 Å. The other H
atoms were positioned with idealized geometry using a riding model with C—H
= 0.93–0.96 Å. All H atoms were refined with isotropic displacement
parameters (set to 1.2 times of the Ueq of the parent atom).
Data collection: CAD-4-PC Software (Enraf–Nonius, 1996); cell refinement: CAD-4-PC Software (Enraf–Nonius, 1996); data reduction: REDU4 (Stoe & Cie, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
3-Methyl-
N-phenylbenzamide
top
Crystal data top
C14H13NO | F(000) = 896 |
Mr = 211.25 | Dx = 1.239 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 16.947 (2) Å | θ = 5.7–21.0° |
b = 15.531 (1) Å | µ = 0.62 mm−1 |
c = 8.623 (1) Å | T = 299 K |
β = 93.35 (1)° | Long needle, colourless |
V = 2265.7 (4) Å3 | 0.60 × 0.10 × 0.05 mm |
Z = 8 | |
Data collection top
Enraf–Nonius CAD4 diffractometer | Rint = 0.034 |
Radiation source: fine-focus sealed tube | θmax = 66.9°, θmin = 2.6° |
Graphite monochromator | h = −20→20 |
ω/2θ scans | k = −1→18 |
4339 measured reflections | l = −10→0 |
4039 independent reflections | 3 standard reflections every 120 min |
2466 reflections with I > 2σ(I) | intensity decay: 1.5% |
Refinement top
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)] = 0.082 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.241 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.153P)2] where P = (Fo2 + 2Fc2)/3 |
4039 reflections | (Δ/σ)max = 0.003 |
291 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
Crystal data top
C14H13NO | V = 2265.7 (4) Å3 |
Mr = 211.25 | Z = 8 |
Monoclinic, P21/c | Cu Kα radiation |
a = 16.947 (2) Å | µ = 0.62 mm−1 |
b = 15.531 (1) Å | T = 299 K |
c = 8.623 (1) Å | 0.60 × 0.10 × 0.05 mm |
β = 93.35 (1)° | |
Data collection top
Enraf–Nonius CAD4 diffractometer | Rint = 0.034 |
4339 measured reflections | 3 standard reflections every 120 min |
4039 independent reflections | intensity decay: 1.5% |
2466 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.082 | 0 restraints |
wR(F2) = 0.241 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.36 e Å−3 |
4039 reflections | Δρmin = −0.39 e Å−3 |
291 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.24023 (18) | 0.66029 (17) | 0.5392 (3) | 0.0558 (8) | |
N1 | 0.26569 (16) | 0.75059 (19) | 0.3424 (3) | 0.0399 (7) | |
H1N | 0.2562 | 0.7611 | 0.2452 | 0.048* | |
C1 | 0.3146 (2) | 0.8100 (2) | 0.4286 (3) | 0.0363 (7) | |
C2 | 0.3052 (2) | 0.8972 (2) | 0.3996 (4) | 0.0457 (9) | |
H2 | 0.2686 | 0.9159 | 0.3224 | 0.055* | |
C3 | 0.3502 (3) | 0.9564 (3) | 0.4849 (5) | 0.0559 (10) | |
H3 | 0.3435 | 1.0150 | 0.4660 | 0.067* | |
C4 | 0.4049 (3) | 0.9287 (3) | 0.5978 (5) | 0.0662 (12) | |
H4 | 0.4342 | 0.9687 | 0.6571 | 0.079* | |
C5 | 0.4163 (3) | 0.8422 (3) | 0.6235 (5) | 0.0611 (12) | |
H5 | 0.4545 | 0.8237 | 0.6980 | 0.073* | |
C6 | 0.3711 (2) | 0.7827 (3) | 0.5385 (4) | 0.0481 (9) | |
H6 | 0.3789 | 0.7241 | 0.5557 | 0.058* | |
C7 | 0.2328 (2) | 0.6791 (2) | 0.3997 (4) | 0.0378 (8) | |
C8 | 0.1875 (2) | 0.6216 (2) | 0.2875 (4) | 0.0382 (8) | |
C9 | 0.1563 (2) | 0.6497 (2) | 0.1438 (4) | 0.0395 (8) | |
H9 | 0.1620 | 0.7071 | 0.1158 | 0.047* | |
C10 | 0.1167 (2) | 0.5932 (3) | 0.0411 (4) | 0.0469 (9) | |
C11 | 0.1086 (2) | 0.5083 (3) | 0.0854 (5) | 0.0553 (10) | |
H11 | 0.0830 | 0.4695 | 0.0173 | 0.066* | |
C12 | 0.1378 (3) | 0.4802 (3) | 0.2293 (5) | 0.0598 (11) | |
H12 | 0.1308 | 0.4232 | 0.2587 | 0.072* | |
C13 | 0.1775 (2) | 0.5369 (2) | 0.3297 (5) | 0.0505 (9) | |
H13 | 0.1976 | 0.5177 | 0.4263 | 0.061* | |
C14 | 0.0866 (3) | 0.6228 (3) | −0.1174 (4) | 0.0639 (12) | |
H14A | 0.0874 | 0.6846 | −0.1213 | 0.077* | |
H14B | 0.0334 | 0.6027 | −0.1380 | 0.077* | |
H14C | 0.1197 | 0.6001 | −0.1942 | 0.077* | |
O2 | 0.26730 (16) | 0.32575 (17) | −0.0183 (3) | 0.0498 (7) | |
N2 | 0.22500 (17) | 0.24790 (19) | 0.1854 (3) | 0.0416 (7) | |
H2N | 0.2375 | 0.2335 | 0.2799 | 0.050* | |
C15 | 0.1546 (2) | 0.2116 (2) | 0.1191 (4) | 0.0396 (8) | |
C16 | 0.1310 (3) | 0.1321 (2) | 0.1709 (4) | 0.0538 (10) | |
H16 | 0.1638 | 0.1014 | 0.2413 | 0.065* | |
C17 | 0.0593 (3) | 0.0978 (3) | 0.1193 (5) | 0.0673 (13) | |
H17 | 0.0429 | 0.0453 | 0.1581 | 0.081* | |
C18 | 0.0117 (3) | 0.1414 (3) | 0.0100 (5) | 0.0664 (12) | |
H18 | −0.0365 | 0.1181 | −0.0258 | 0.080* | |
C19 | 0.0360 (3) | 0.2189 (3) | −0.0454 (5) | 0.0603 (11) | |
H19 | 0.0046 | 0.2477 | −0.1207 | 0.072* | |
C20 | 0.1070 (2) | 0.2549 (3) | 0.0098 (4) | 0.0453 (9) | |
H20 | 0.1226 | 0.3083 | −0.0268 | 0.054* | |
C21 | 0.2752 (2) | 0.3022 (2) | 0.1197 (4) | 0.0386 (8) | |
C22 | 0.3426 (2) | 0.3328 (2) | 0.2230 (4) | 0.0384 (8) | |
C23 | 0.3317 (2) | 0.3609 (2) | 0.3741 (4) | 0.0427 (8) | |
H23 | 0.2813 | 0.3599 | 0.4114 | 0.051* | |
C24 | 0.3942 (2) | 0.3902 (2) | 0.4689 (4) | 0.0458 (9) | |
C25 | 0.4691 (2) | 0.3895 (2) | 0.4135 (5) | 0.0503 (9) | |
H25 | 0.5121 | 0.4079 | 0.4772 | 0.060* | |
C26 | 0.4808 (2) | 0.3617 (3) | 0.2633 (5) | 0.0529 (10) | |
H26 | 0.5314 | 0.3614 | 0.2270 | 0.063* | |
C27 | 0.4178 (2) | 0.3347 (2) | 0.1686 (4) | 0.0462 (9) | |
H27 | 0.4257 | 0.3176 | 0.0673 | 0.055* | |
C28 | 0.3808 (3) | 0.4223 (3) | 0.6316 (5) | 0.0706 (14) | |
H28A | 0.3665 | 0.3748 | 0.6955 | 0.085* | |
H28B | 0.3391 | 0.4642 | 0.6270 | 0.085* | |
H28C | 0.4285 | 0.4483 | 0.6753 | 0.085* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.095 (2) | 0.0574 (16) | 0.0143 (12) | −0.0142 (14) | −0.0011 (12) | 0.0030 (10) |
N1 | 0.0552 (17) | 0.0488 (16) | 0.0154 (12) | −0.0071 (14) | −0.0001 (12) | −0.0003 (11) |
C1 | 0.0451 (18) | 0.0481 (19) | 0.0160 (14) | −0.0036 (15) | 0.0039 (13) | −0.0036 (13) |
C2 | 0.056 (2) | 0.054 (2) | 0.0275 (18) | −0.0009 (17) | 0.0043 (16) | 0.0017 (15) |
C3 | 0.076 (3) | 0.047 (2) | 0.044 (2) | −0.0084 (19) | 0.001 (2) | −0.0009 (17) |
C4 | 0.087 (3) | 0.065 (3) | 0.045 (2) | −0.020 (2) | −0.006 (2) | −0.011 (2) |
C5 | 0.068 (3) | 0.073 (3) | 0.040 (2) | −0.011 (2) | −0.016 (2) | 0.002 (2) |
C6 | 0.056 (2) | 0.051 (2) | 0.037 (2) | −0.0034 (17) | −0.0014 (17) | 0.0017 (16) |
C7 | 0.0488 (19) | 0.0458 (19) | 0.0191 (15) | 0.0027 (15) | 0.0043 (14) | −0.0037 (14) |
C8 | 0.048 (2) | 0.0444 (19) | 0.0229 (16) | −0.0005 (15) | 0.0054 (14) | −0.0051 (13) |
C9 | 0.0483 (19) | 0.0498 (19) | 0.0204 (16) | −0.0092 (16) | 0.0036 (14) | −0.0035 (14) |
C10 | 0.050 (2) | 0.061 (2) | 0.0303 (19) | −0.0054 (17) | 0.0034 (16) | −0.0093 (16) |
C11 | 0.059 (2) | 0.059 (2) | 0.047 (2) | −0.011 (2) | 0.0019 (19) | −0.0190 (19) |
C12 | 0.079 (3) | 0.042 (2) | 0.058 (3) | −0.008 (2) | −0.005 (2) | −0.0042 (18) |
C13 | 0.069 (3) | 0.045 (2) | 0.037 (2) | −0.0001 (18) | −0.0004 (18) | 0.0015 (16) |
C14 | 0.069 (3) | 0.090 (3) | 0.031 (2) | −0.014 (2) | −0.0042 (19) | −0.008 (2) |
O2 | 0.0733 (18) | 0.0608 (16) | 0.0150 (11) | −0.0113 (13) | 0.0008 (11) | 0.0021 (10) |
N2 | 0.0548 (17) | 0.0534 (17) | 0.0163 (13) | −0.0067 (14) | −0.0002 (12) | 0.0036 (12) |
C15 | 0.050 (2) | 0.050 (2) | 0.0192 (15) | −0.0040 (16) | 0.0036 (14) | −0.0074 (14) |
C16 | 0.079 (3) | 0.052 (2) | 0.0304 (19) | −0.008 (2) | 0.0043 (18) | −0.0029 (16) |
C17 | 0.088 (3) | 0.070 (3) | 0.044 (2) | −0.029 (3) | 0.006 (2) | −0.008 (2) |
C18 | 0.066 (3) | 0.089 (3) | 0.044 (2) | −0.021 (2) | 0.003 (2) | −0.014 (2) |
C19 | 0.062 (2) | 0.081 (3) | 0.037 (2) | 0.004 (2) | −0.0015 (19) | −0.008 (2) |
C20 | 0.052 (2) | 0.058 (2) | 0.0252 (17) | 0.0003 (18) | 0.0017 (15) | −0.0019 (15) |
C21 | 0.0509 (19) | 0.0455 (19) | 0.0197 (15) | 0.0023 (15) | 0.0041 (14) | −0.0045 (13) |
C22 | 0.050 (2) | 0.0424 (19) | 0.0223 (16) | −0.0011 (15) | 0.0013 (14) | 0.0011 (13) |
C23 | 0.052 (2) | 0.051 (2) | 0.0248 (17) | −0.0048 (16) | 0.0032 (15) | −0.0019 (15) |
C24 | 0.060 (2) | 0.048 (2) | 0.0282 (18) | −0.0052 (17) | −0.0064 (17) | −0.0034 (15) |
C25 | 0.054 (2) | 0.053 (2) | 0.043 (2) | −0.0016 (17) | −0.0085 (18) | 0.0002 (17) |
C26 | 0.047 (2) | 0.060 (2) | 0.052 (2) | 0.0024 (18) | 0.0040 (18) | 0.0027 (19) |
C27 | 0.054 (2) | 0.053 (2) | 0.0325 (19) | 0.0030 (17) | 0.0077 (16) | −0.0011 (16) |
C28 | 0.085 (3) | 0.092 (3) | 0.034 (2) | −0.021 (3) | −0.002 (2) | −0.023 (2) |
Geometric parameters (Å, º) top
O1—C7 | 1.237 (4) | O2—C21 | 1.244 (4) |
N1—C7 | 1.348 (4) | N2—C21 | 1.347 (4) |
N1—C1 | 1.421 (4) | N2—C15 | 1.409 (4) |
N1—H1N | 0.8600 | N2—H2N | 0.8600 |
C1—C6 | 1.373 (5) | C15—C20 | 1.379 (5) |
C1—C2 | 1.385 (5) | C15—C16 | 1.382 (5) |
C2—C3 | 1.379 (5) | C16—C17 | 1.376 (6) |
C2—H2 | 0.9300 | C16—H16 | 0.9300 |
C3—C4 | 1.373 (6) | C17—C18 | 1.381 (7) |
C3—H3 | 0.9300 | C17—H17 | 0.9300 |
C4—C5 | 1.373 (6) | C18—C19 | 1.368 (6) |
C4—H4 | 0.9300 | C18—H18 | 0.9300 |
C5—C6 | 1.384 (5) | C19—C20 | 1.386 (5) |
C5—H5 | 0.9300 | C19—H19 | 0.9300 |
C6—H6 | 0.9300 | C20—H20 | 0.9300 |
C7—C8 | 1.496 (5) | C21—C22 | 1.484 (5) |
C8—C13 | 1.378 (5) | C22—C27 | 1.384 (5) |
C8—C9 | 1.389 (5) | C22—C23 | 1.397 (5) |
C9—C10 | 1.391 (5) | C23—C24 | 1.376 (5) |
C9—H9 | 0.9300 | C23—H23 | 0.9300 |
C10—C11 | 1.382 (6) | C24—C25 | 1.383 (6) |
C10—C14 | 1.503 (5) | C24—C28 | 1.519 (5) |
C11—C12 | 1.380 (6) | C25—C26 | 1.391 (6) |
C11—H11 | 0.9300 | C25—H25 | 0.9300 |
C12—C13 | 1.382 (5) | C26—C27 | 1.372 (5) |
C12—H12 | 0.9300 | C26—H26 | 0.9300 |
C13—H13 | 0.9300 | C27—H27 | 0.9300 |
C14—H14A | 0.9600 | C28—H28A | 0.9600 |
C14—H14B | 0.9600 | C28—H28B | 0.9600 |
C14—H14C | 0.9600 | C28—H28C | 0.9600 |
| | | |
C7—N1—C1 | 125.7 (3) | C21—N2—C15 | 128.3 (3) |
C7—N1—H1N | 117.1 | C21—N2—H2N | 115.8 |
C1—N1—H1N | 117.1 | C15—N2—H2N | 115.8 |
C6—C1—C2 | 119.6 (3) | C20—C15—C16 | 119.2 (3) |
C6—C1—N1 | 121.5 (3) | C20—C15—N2 | 122.0 (3) |
C2—C1—N1 | 118.9 (3) | C16—C15—N2 | 118.8 (3) |
C3—C2—C1 | 120.2 (4) | C17—C16—C15 | 120.6 (4) |
C3—C2—H2 | 119.9 | C17—C16—H16 | 119.7 |
C1—C2—H2 | 119.9 | C15—C16—H16 | 119.7 |
C4—C3—C2 | 119.8 (4) | C16—C17—C18 | 120.0 (4) |
C4—C3—H3 | 120.1 | C16—C17—H17 | 120.0 |
C2—C3—H3 | 120.1 | C18—C17—H17 | 120.0 |
C5—C4—C3 | 120.3 (4) | C19—C18—C17 | 119.6 (4) |
C5—C4—H4 | 119.8 | C19—C18—H18 | 120.2 |
C3—C4—H4 | 119.8 | C17—C18—H18 | 120.2 |
C4—C5—C6 | 119.9 (4) | C18—C19—C20 | 120.6 (4) |
C4—C5—H5 | 120.0 | C18—C19—H19 | 119.7 |
C6—C5—H5 | 120.0 | C20—C19—H19 | 119.7 |
C1—C6—C5 | 120.1 (4) | C15—C20—C19 | 119.9 (4) |
C1—C6—H6 | 120.0 | C15—C20—H20 | 120.0 |
C5—C6—H6 | 120.0 | C19—C20—H20 | 120.0 |
O1—C7—N1 | 122.0 (3) | O2—C21—N2 | 123.4 (3) |
O1—C7—C8 | 120.4 (3) | O2—C21—C22 | 121.1 (3) |
N1—C7—C8 | 117.5 (3) | N2—C21—C22 | 115.5 (3) |
C13—C8—C9 | 119.3 (3) | C27—C22—C23 | 118.9 (3) |
C13—C8—C7 | 117.8 (3) | C27—C22—C21 | 119.7 (3) |
C9—C8—C7 | 123.0 (3) | C23—C22—C21 | 121.4 (3) |
C8—C9—C10 | 121.0 (3) | C24—C23—C22 | 121.2 (3) |
C8—C9—H9 | 119.5 | C24—C23—H23 | 119.4 |
C10—C9—H9 | 119.5 | C22—C23—H23 | 119.4 |
C11—C10—C9 | 118.5 (4) | C23—C24—C25 | 118.9 (3) |
C11—C10—C14 | 120.7 (4) | C23—C24—C28 | 120.4 (4) |
C9—C10—C14 | 120.8 (4) | C25—C24—C28 | 120.7 (4) |
C12—C11—C10 | 121.0 (4) | C24—C25—C26 | 120.5 (4) |
C12—C11—H11 | 119.5 | C24—C25—H25 | 119.7 |
C10—C11—H11 | 119.5 | C26—C25—H25 | 119.7 |
C11—C12—C13 | 119.9 (4) | C27—C26—C25 | 120.1 (4) |
C11—C12—H12 | 120.1 | C27—C26—H26 | 120.0 |
C13—C12—H12 | 120.1 | C25—C26—H26 | 120.0 |
C8—C13—C12 | 120.4 (4) | C26—C27—C22 | 120.4 (4) |
C8—C13—H13 | 119.8 | C26—C27—H27 | 119.8 |
C12—C13—H13 | 119.8 | C22—C27—H27 | 119.8 |
C10—C14—H14A | 109.5 | C24—C28—H28A | 109.5 |
C10—C14—H14B | 109.5 | C24—C28—H28B | 109.5 |
H14A—C14—H14B | 109.5 | H28A—C28—H28B | 109.5 |
C10—C14—H14C | 109.5 | C24—C28—H28C | 109.5 |
H14A—C14—H14C | 109.5 | H28A—C28—H28C | 109.5 |
H14B—C14—H14C | 109.5 | H28B—C28—H28C | 109.5 |
| | | |
C7—N1—C1—C6 | 40.6 (5) | C21—N2—C15—C20 | −32.3 (5) |
C7—N1—C1—C2 | −139.9 (4) | C21—N2—C15—C16 | 150.9 (4) |
C6—C1—C2—C3 | −2.6 (5) | C20—C15—C16—C17 | −2.7 (6) |
N1—C1—C2—C3 | 178.0 (3) | N2—C15—C16—C17 | 174.2 (4) |
C1—C2—C3—C4 | 0.6 (6) | C15—C16—C17—C18 | 2.7 (7) |
C2—C3—C4—C5 | 1.6 (7) | C16—C17—C18—C19 | −0.6 (7) |
C3—C4—C5—C6 | −1.9 (7) | C17—C18—C19—C20 | −1.5 (7) |
C2—C1—C6—C5 | 2.3 (5) | C16—C15—C20—C19 | 0.7 (5) |
N1—C1—C6—C5 | −178.2 (4) | N2—C15—C20—C19 | −176.2 (3) |
C4—C5—C6—C1 | −0.1 (6) | C18—C19—C20—C15 | 1.4 (6) |
C1—N1—C7—O1 | 3.1 (6) | C15—N2—C21—O2 | −3.5 (6) |
C1—N1—C7—C8 | −176.0 (3) | C15—N2—C21—C22 | 177.0 (3) |
O1—C7—C8—C13 | −21.2 (5) | O2—C21—C22—C27 | −44.0 (5) |
N1—C7—C8—C13 | 157.9 (3) | N2—C21—C22—C27 | 135.6 (3) |
O1—C7—C8—C9 | 159.5 (3) | O2—C21—C22—C23 | 135.1 (4) |
N1—C7—C8—C9 | −21.4 (5) | N2—C21—C22—C23 | −45.3 (5) |
C13—C8—C9—C10 | −1.4 (5) | C27—C22—C23—C24 | −0.1 (5) |
C7—C8—C9—C10 | 177.9 (3) | C21—C22—C23—C24 | −179.2 (3) |
C8—C9—C10—C11 | 0.4 (6) | C22—C23—C24—C25 | −1.5 (6) |
C8—C9—C10—C14 | −176.9 (4) | C22—C23—C24—C28 | 178.6 (4) |
C9—C10—C11—C12 | 1.1 (6) | C23—C24—C25—C26 | 1.5 (6) |
C14—C10—C11—C12 | 178.4 (4) | C28—C24—C25—C26 | −178.7 (4) |
C10—C11—C12—C13 | −1.6 (7) | C24—C25—C26—C27 | 0.1 (6) |
C9—C8—C13—C12 | 0.9 (6) | C25—C26—C27—C22 | −1.7 (6) |
C7—C8—C13—C12 | −178.5 (4) | C23—C22—C27—C26 | 1.7 (5) |
C11—C12—C13—C8 | 0.6 (7) | C21—C22—C27—C26 | −179.2 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.86 | 2.16 | 2.968 (4) | 157 |
N2—H2N···O2ii | 0.86 | 2.01 | 2.853 (3) | 168 |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+1/2, z+1/2. |
Experimental details
Crystal data |
Chemical formula | C14H13NO |
Mr | 211.25 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 299 |
a, b, c (Å) | 16.947 (2), 15.531 (1), 8.623 (1) |
β (°) | 93.35 (1) |
V (Å3) | 2265.7 (4) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 0.62 |
Crystal size (mm) | 0.60 × 0.10 × 0.05 |
|
Data collection |
Diffractometer | Enraf–Nonius CAD4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4339, 4039, 2466 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.597 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.082, 0.241, 1.03 |
No. of reflections | 4039 |
No. of parameters | 291 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.36, −0.39 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.86 | 2.16 | 2.968 (4) | 156.5 |
N2—H2N···O2ii | 0.86 | 2.01 | 2.853 (3) | 167.7 |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+1/2, z+1/2. |
As part of a study of the substituent effects on the structures of benzanilides, in the present work, the structure of 3-methyl-N-(phenyl)benzamide (NP3MBA) has been determined (Gowda et al., 2003, 2008a,b).
The asymmetric unit of the structure of NP3MBA contains two molecules (Fig. 1). The conformation of the C═O bonds are anti to the meta-methyl substituents in the benzoyl phenyl rings. The conformations of the N—H and C═O bonds in the –NH—CO– groups are also anti to each other. The bond parameters in NP3MBA are similar to those in N-(phenyl)benzamide, 2-methyl-N-(phenyl)benzamide and other benzanilides (Gowda et al., 2003, 2008a,b). The amide group –NHCO– forms the dihedral angles of 20.97 (34)° (molecule 1) and 45.65(0.19) (molecule 2) with the benzoyl ring, and 41.54 (25)° (molecule 1), 31.87(0.29) (molecule 2) with the aniline ring. The benzoyl and the aniline rings have the dihedral angles of 22.17 (18)°) (molecule 1) and 75.86(0.12) (molecule 2).
The packing diagram of NP3MBA molecules showing the hydrogen bonds N1—H1N···O1, N2—H2N···O2 (Table 1) involved in the formation of molecular chain is shown in Fig. 2.