organic compounds
N-(2,3-Dimethylphenyl)-2-methylbenzamide
aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, bInstitute of Mathematics and Physics, Faculty of Mechanical Engineering, Slovak Technical University, Namestie slobody 17, SK-812 31 Bratislava, Slovak Republic, and cInstitute of Physical Chemistry and Chemical Physics, Faculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic
*Correspondence e-mail: gowdabt@yahoo.com
In the title compound, C16H17NO, the two aromatic rings make a dihedral angle of 5.9 (2)°, while the central amide core –NH—C(=O)– is twisted by 44.0 (3) and 47.1 (3)° out of the planes of the 2,3-dimethylphenyl and 2-methylphenyl rings, respectively. In the crystal, N—H⋯O hydrogen bonds link the molecules into infinite chains running along the b axis.
Related literature
For the preparation of the title compound, see: Gowda et al. (2003). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003); Gowda et al. (2000); Saeed et al. (2010) on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004), on N-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005) and on N-chloroarylamides, see: Gowda et al. (1996).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2002) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009) and WinGX (Farrugia, 1999).
Supporting information
https://doi.org/10.1107/S1600536811050732/bt5725sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050732/bt5725Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536811050732/bt5725Isup3.cml
The title compound was prepared according to the method described by 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. Plate like colourless single crystals of the title compound were obtained by slow evaporation of an ethanol solution of the compound (0.5 g in about 30 ml of ethanol) at room temperature.
All hydrogen atoms except amide H atom were placed in calculated positions with C–H distances in the range 0.93–0.96 Å and constrained to ride on their parent atoms. The amide H atom was found in a difference map and was refined with the N—H distance restrained to 0.86 (3) Å. The Uĩso~(H) values were set at 1.2Ueq(C-aromatic, N) or 1.5Ueq(C-methyl). In the absence of significant
the could not be reliably determined and then the Friedel pairs were merged and any references to the were removed.The amide and sulfonamide moieties are the constituents of many biologically significant compounds. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bowes et al., 2003; Gowda et al., 2000; Saeed et al., 2010), N-(aryl)-methanesulfonamides (Jayalakshmi & Gowda, 2004), N-(aryl)-arylsulfonamides (Shetty & Gowda, 2005) and N-chloro-arylsulfonamides (Gowda et al., 1996), in the present work, the
of N-(2,3-dimethylphenyl)-2-methylbenzamide (I) has been determined (Fig. 1).In (I), the two aromatic rings make the dihedral angle of 5.9 (2)°, while the central amide core –NH—C(=O)– is twisted by 44.0 (3) ° and 47.1 (3)° out of the planes of the 2,3-dimethylphenyl and 2-methylphenyl rings, respectively.
Further, the ortho-methyl group in the benzoyl ring is positioned syn to the C=O bond and so also the ortho- and meta- methyl groups in the anilino ring to the N—H bond, while the N—H and C=O bonds in the C—NH—C(O)—C segment are anti to each other.
In the
intermolecular N—H···O hydrogen bonds link the molecules into infinite chains running along the b-axis. Part of the is shown in Fig. 2.For the preparation of the title compound, see: Gowda et al. (2003). For our studies on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003); Gowda et al. (2000); Saeed et al. (2010) on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004), on N-(aryl)-arylsulfonamides, see: Shetty & Gowda (2005) and on N-chloroarylamides, see: Gowda et al. (1996).
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell
CrysAlis CCD (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2002) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).C16H17NO | F(000) = 256 |
Mr = 239.31 | Dx = 1.201 Mg m−3 |
Monoclinic, Pc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P -2yc | Cell parameters from 6163 reflections |
a = 5.8092 (4) Å | θ = 3.5–25.0° |
b = 4.9253 (2) Å | µ = 0.08 mm−1 |
c = 23.1887 (12) Å | T = 295 K |
β = 94.229 (5)° | Plate, colourless |
V = 661.67 (6) Å3 | 0.50 × 0.30 × 0.10 mm |
Z = 2 |
Oxford Diffractio Xcalibur System diffractometer | 1162 independent reflections |
Radiation source: fine-focus sealed tube | 1021 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
Detector resolution: 0 pixels mm-1 | θmax = 25.0°, θmin = 3.5° |
\j scans, and ω scans with κ offsets | h = −6→6 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | k = −5→5 |
Tmin = 0.962, Tmax = 0.993 | l = −27→27 |
9487 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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.208 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.122P)2 + 0.430P] where P = (Fo2 + 2Fc2)/3 |
1162 reflections | (Δ/σ)max < 0.001 |
170 parameters | Δρmax = 0.29 e Å−3 |
3 restraints | Δρmin = −0.23 e Å−3 |
C16H17NO | V = 661.67 (6) Å3 |
Mr = 239.31 | Z = 2 |
Monoclinic, Pc | Mo Kα radiation |
a = 5.8092 (4) Å | µ = 0.08 mm−1 |
b = 4.9253 (2) Å | T = 295 K |
c = 23.1887 (12) Å | 0.50 × 0.30 × 0.10 mm |
β = 94.229 (5)° |
Oxford Diffractio Xcalibur System diffractometer | 1162 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009) | 1021 reflections with I > 2σ(I) |
Tmin = 0.962, Tmax = 0.993 | Rint = 0.043 |
9487 measured reflections |
R[F2 > 2σ(F2)] = 0.068 | 3 restraints |
wR(F2) = 0.208 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.29 e Å−3 |
1162 reflections | Δρmin = −0.23 e Å−3 |
170 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.7345 (9) | 0.2228 (10) | 0.2068 (2) | 0.0440 (13) | |
C2 | 0.9138 (11) | 0.3524 (12) | 0.1826 (3) | 0.0507 (14) | |
C3 | 0.9528 (11) | 0.3043 (14) | 0.1241 (3) | 0.0582 (16) | |
C4 | 0.8099 (14) | 0.1135 (15) | 0.0929 (3) | 0.069 (2) | |
H4 | 0.8364 | 0.0739 | 0.0548 | 0.083* | |
C5 | 0.6384 (13) | −0.0099 (15) | 0.1175 (3) | 0.0661 (19) | |
H5 | 0.5456 | −0.1324 | 0.0959 | 0.079* | |
C6 | 0.5950 (12) | 0.0403 (13) | 0.1744 (3) | 0.0582 (16) | |
H6 | 0.4740 | −0.0471 | 0.1909 | 0.070* | |
C7 | 1.0716 (12) | 0.5454 (14) | 0.2186 (4) | 0.069 (2) | |
H7A | 1.2242 | 0.5380 | 0.2054 | 0.104* | |
H7B | 1.0768 | 0.4924 | 0.2585 | 0.104* | |
H7C | 1.0130 | 0.7272 | 0.2145 | 0.104* | |
C8 | 1.1354 (16) | 0.4573 (18) | 0.0958 (4) | 0.081 (2) | |
H8A | 1.1608 | 0.3746 | 0.0593 | 0.122* | |
H8B | 1.2761 | 0.4538 | 0.1203 | 0.122* | |
H8C | 1.0868 | 0.6420 | 0.0896 | 0.122* | |
C9 | 0.6479 (10) | 0.0862 (11) | 0.3048 (2) | 0.0446 (13) | |
C10 | 0.6090 (11) | 0.1940 (11) | 0.3638 (2) | 0.0485 (14) | |
C11 | 0.4282 (10) | 0.1026 (12) | 0.3934 (3) | 0.0520 (15) | |
C12 | 0.4113 (16) | 0.2012 (17) | 0.4479 (3) | 0.075 (2) | |
H12 | 0.2908 | 0.1411 | 0.4689 | 0.090* | |
C13 | 0.5661 (15) | 0.3872 (16) | 0.4731 (3) | 0.072 (2) | |
H13 | 0.5472 | 0.4519 | 0.5102 | 0.086* | |
C14 | 0.7478 (14) | 0.4764 (15) | 0.4435 (3) | 0.0680 (19) | |
H14 | 0.8540 | 0.5996 | 0.4603 | 0.082* | |
C15 | 0.7695 (10) | 0.3809 (13) | 0.3890 (3) | 0.0528 (15) | |
H15 | 0.8913 | 0.4397 | 0.3683 | 0.063* | |
C16 | 0.2533 (14) | −0.0985 (15) | 0.3695 (4) | 0.074 (2) | |
H16A | 0.1224 | −0.0972 | 0.3925 | 0.111* | |
H16B | 0.3206 | −0.2766 | 0.3703 | 0.111* | |
H16C | 0.2046 | −0.0508 | 0.3304 | 0.111* | |
N1 | 0.6911 (9) | 0.2757 (9) | 0.2654 (2) | 0.0478 (12) | |
H1 | 0.756 (11) | 0.427 (8) | 0.276 (3) | 0.06 (2)* | |
O1 | 0.6366 (11) | −0.1558 (8) | 0.2943 (2) | 0.0708 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.054 (3) | 0.029 (2) | 0.049 (3) | 0.002 (2) | 0.003 (2) | −0.003 (2) |
C2 | 0.059 (4) | 0.029 (3) | 0.063 (4) | 0.005 (2) | 0.000 (3) | 0.001 (2) |
C3 | 0.057 (4) | 0.052 (4) | 0.066 (4) | 0.005 (3) | 0.008 (3) | 0.015 (3) |
C4 | 0.098 (6) | 0.065 (4) | 0.044 (3) | 0.012 (4) | 0.007 (4) | 0.003 (3) |
C5 | 0.090 (5) | 0.056 (4) | 0.050 (4) | −0.014 (4) | −0.005 (3) | −0.013 (3) |
C6 | 0.072 (4) | 0.047 (3) | 0.055 (4) | −0.010 (3) | −0.001 (3) | −0.006 (3) |
C7 | 0.062 (4) | 0.052 (4) | 0.094 (5) | −0.021 (3) | 0.005 (3) | −0.012 (4) |
C8 | 0.094 (5) | 0.077 (5) | 0.076 (5) | 0.006 (5) | 0.025 (4) | 0.023 (4) |
C9 | 0.053 (3) | 0.032 (3) | 0.049 (3) | 0.002 (2) | 0.007 (2) | 0.000 (2) |
C10 | 0.068 (4) | 0.031 (3) | 0.046 (3) | 0.008 (3) | −0.002 (3) | 0.002 (2) |
C11 | 0.056 (4) | 0.036 (3) | 0.065 (4) | 0.001 (3) | 0.007 (3) | 0.003 (3) |
C12 | 0.091 (6) | 0.070 (5) | 0.064 (4) | −0.002 (4) | 0.015 (4) | 0.009 (4) |
C13 | 0.103 (6) | 0.061 (4) | 0.049 (4) | −0.006 (4) | −0.001 (4) | −0.001 (3) |
C14 | 0.086 (5) | 0.059 (4) | 0.058 (4) | −0.008 (4) | 0.001 (3) | −0.010 (3) |
C15 | 0.059 (4) | 0.048 (3) | 0.051 (3) | −0.006 (3) | −0.001 (3) | 0.002 (3) |
C16 | 0.072 (5) | 0.048 (4) | 0.104 (6) | −0.012 (3) | 0.011 (4) | −0.008 (4) |
N1 | 0.060 (3) | 0.028 (2) | 0.056 (3) | −0.008 (2) | 0.012 (2) | −0.004 (2) |
O1 | 0.120 (4) | 0.028 (2) | 0.066 (3) | 0.003 (2) | 0.019 (2) | 0.001 (2) |
C1—C2 | 1.376 (9) | C9—O1 | 1.217 (7) |
C1—C6 | 1.392 (8) | C9—N1 | 1.342 (7) |
C1—N1 | 1.424 (7) | C9—C10 | 1.502 (8) |
C2—C3 | 1.412 (9) | C10—C11 | 1.373 (9) |
C2—C7 | 1.526 (9) | C10—C15 | 1.406 (9) |
C3—C4 | 1.416 (10) | C11—C12 | 1.362 (10) |
C3—C8 | 1.491 (11) | C11—C16 | 1.496 (9) |
C4—C5 | 1.330 (11) | C12—C13 | 1.383 (11) |
C4—H4 | 0.9300 | C12—H12 | 0.9300 |
C5—C6 | 1.385 (10) | C13—C14 | 1.374 (11) |
C5—H5 | 0.9300 | C13—H13 | 0.9300 |
C6—H6 | 0.9300 | C14—C15 | 1.363 (10) |
C7—H7A | 0.9600 | C14—H14 | 0.9300 |
C7—H7B | 0.9600 | C15—H15 | 0.9300 |
C7—H7C | 0.9600 | C16—H16A | 0.9600 |
C8—H8A | 0.9600 | C16—H16B | 0.9600 |
C8—H8B | 0.9600 | C16—H16C | 0.9600 |
C8—H8C | 0.9600 | N1—H1 | 0.860 (5) |
C2—C1—C6 | 120.5 (5) | O1—C9—N1 | 123.8 (6) |
C2—C1—N1 | 119.8 (5) | O1—C9—C10 | 121.2 (5) |
C6—C1—N1 | 119.7 (5) | N1—C9—C10 | 115.0 (5) |
C1—C2—C3 | 119.6 (5) | C11—C10—C15 | 121.0 (5) |
C1—C2—C7 | 120.5 (6) | C11—C10—C9 | 120.8 (5) |
C3—C2—C7 | 119.9 (6) | C15—C10—C9 | 118.0 (6) |
C2—C3—C4 | 118.1 (6) | C12—C11—C10 | 117.2 (6) |
C2—C3—C8 | 120.5 (7) | C12—C11—C16 | 119.1 (6) |
C4—C3—C8 | 121.4 (7) | C10—C11—C16 | 123.7 (6) |
C5—C4—C3 | 121.0 (6) | C11—C12—C13 | 122.6 (7) |
C5—C4—H4 | 119.5 | C11—C12—H12 | 118.7 |
C3—C4—H4 | 119.5 | C13—C12—H12 | 118.7 |
C4—C5—C6 | 121.4 (6) | C14—C13—C12 | 120.0 (7) |
C4—C5—H5 | 119.3 | C14—C13—H13 | 120.0 |
C6—C5—H5 | 119.3 | C12—C13—H13 | 120.0 |
C5—C6—C1 | 119.3 (6) | C15—C14—C13 | 118.7 (7) |
C5—C6—H6 | 120.3 | C15—C14—H14 | 120.6 |
C1—C6—H6 | 120.3 | C13—C14—H14 | 120.6 |
C2—C7—H7A | 109.5 | C14—C15—C10 | 120.4 (6) |
C2—C7—H7B | 109.5 | C14—C15—H15 | 119.8 |
H7A—C7—H7B | 109.5 | C10—C15—H15 | 119.8 |
C2—C7—H7C | 109.5 | C11—C16—H16A | 109.5 |
H7A—C7—H7C | 109.5 | C11—C16—H16B | 109.5 |
H7B—C7—H7C | 109.5 | H16A—C16—H16B | 109.5 |
C3—C8—H8A | 109.5 | C11—C16—H16C | 109.5 |
C3—C8—H8B | 109.5 | H16A—C16—H16C | 109.5 |
H8A—C8—H8B | 109.5 | H16B—C16—H16C | 109.5 |
C3—C8—H8C | 109.5 | C9—N1—C1 | 125.3 (5) |
H8A—C8—H8C | 109.5 | C9—N1—H1 | 121 (5) |
H8B—C8—H8C | 109.5 | C1—N1—H1 | 108 (5) |
C6—C1—C2—C3 | 1.5 (8) | N1—C9—C10—C15 | −49.1 (7) |
N1—C1—C2—C3 | −178.5 (5) | C15—C10—C11—C12 | 0.2 (9) |
C6—C1—C2—C7 | −178.0 (6) | C9—C10—C11—C12 | 177.0 (6) |
N1—C1—C2—C7 | 2.0 (8) | C15—C10—C11—C16 | −179.2 (6) |
C1—C2—C3—C4 | −2.6 (9) | C9—C10—C11—C16 | −2.4 (9) |
C7—C2—C3—C4 | 176.9 (6) | C10—C11—C12—C13 | 0.5 (11) |
C1—C2—C3—C8 | 175.6 (6) | C16—C11—C12—C13 | 179.9 (8) |
C7—C2—C3—C8 | −4.9 (9) | C11—C12—C13—C14 | −1.0 (13) |
C2—C3—C4—C5 | 2.4 (10) | C12—C13—C14—C15 | 0.8 (12) |
C8—C3—C4—C5 | −175.9 (7) | C13—C14—C15—C10 | −0.2 (11) |
C3—C4—C5—C6 | −0.9 (12) | C11—C10—C15—C14 | −0.3 (10) |
C4—C5—C6—C1 | −0.3 (11) | C9—C10—C15—C14 | −177.2 (6) |
C2—C1—C6—C5 | 0.0 (9) | O1—C9—N1—C1 | −1.4 (10) |
N1—C1—C6—C5 | 180.0 (6) | C10—C9—N1—C1 | 179.7 (6) |
O1—C9—C10—C11 | −45.0 (9) | C2—C1—N1—C9 | −134.7 (6) |
N1—C9—C10—C11 | 133.9 (6) | C6—C1—N1—C9 | 45.3 (8) |
O1—C9—C10—C15 | 132.0 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 (1) | 2.23 (5) | 2.903 (6) | 136 (6) |
Symmetry code: (i) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C16H17NO |
Mr | 239.31 |
Crystal system, space group | Monoclinic, Pc |
Temperature (K) | 295 |
a, b, c (Å) | 5.8092 (4), 4.9253 (2), 23.1887 (12) |
β (°) | 94.229 (5) |
V (Å3) | 661.67 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.50 × 0.30 × 0.10 |
Data collection | |
Diffractometer | Oxford Diffractio Xcalibur System |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.962, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9487, 1162, 1021 |
Rint | 0.043 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.068, 0.208, 1.10 |
No. of reflections | 1162 |
No. of parameters | 170 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.29, −0.23 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2002) and ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.860 (5) | 2.23 (5) | 2.903 (6) | 136 (6) |
Symmetry code: (i) x, y+1, z. |
Acknowledgements
VZR thanks the University Grants Commission, Government of India, New Delhi, for the award of an RFSMS research fellowship. JS, VV and JK thank the VEGA Grant Agency of the Slovak Ministry of Education (1/0679/11) and the Research and Development Agency of Slovakia (APVV-0202/10) for financial support and the Structural Funds, Interreg IIIA, for financial support in purchasing the diffractometer.
References
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The amide and sulfonamide moieties are the constituents of many biologically significant compounds. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bowes et al., 2003; Gowda et al., 2000; Saeed et al., 2010), N-(aryl)-methanesulfonamides (Jayalakshmi & Gowda, 2004), N-(aryl)-arylsulfonamides (Shetty & Gowda, 2005) and N-chloro-arylsulfonamides (Gowda et al., 1996), in the present work, the crystal structure of N-(2,3-dimethylphenyl)-2-methylbenzamide (I) has been determined (Fig. 1).
In (I), the two aromatic rings make the dihedral angle of 5.9 (2)°, while the central amide core –NH—C(=O)– is twisted by 44.0 (3) ° and 47.1 (3)° out of the planes of the 2,3-dimethylphenyl and 2-methylphenyl rings, respectively.
Further, the ortho-methyl group in the benzoyl ring is positioned syn to the C=O bond and so also the ortho- and meta- methyl groups in the anilino ring to the N—H bond, while the N—H and C=O bonds in the C—NH—C(O)—C segment are anti to each other.
In the crystal structure, intermolecular N—H···O hydrogen bonds link the molecules into infinite chains running along the b-axis. Part of the crystal structure is shown in Fig. 2.