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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

3-Anilino-N-p-tolyl­benzamide

aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
*Correspondence e-mail: qindabincwnu@yahoo.com.cn

(Received 2 September 2009; accepted 20 November 2009; online 12 December 2009)

The title compound, C20H18N2O, which crystallizes with two independent mol­ecules (A and B) in the asymmetric unit, is composed of three aromatic rings (I, II and III). The conformation of the two independent mol­ecules is slightly different. The dihedral angles between the central aromatic ring II and rings I and III are 47.13 (9) and 89.36 (9)°, respectively, for mol­ecule A, and 29.60 (9) and 70.72 (9)°, respectively, for mol­ecule B. Rings I and III are inclined to one another by 86.57 (9)° in mol­ecule A, and 64.59 (10)° in mol­ecule B. The mol­ecular structures are stabilized by intra­molecular N—H⋯O hydrogen bonds. In the crystal structure, mol­ecules are linked through inter­molecular N—H⋯O hydrogen bonds, forming chains propagating in the [010] direction. In addition, a number of C—H⋯π inter­actions are observed.

Related literature

For the synthesis, see: Martín et al. (2006[Martín, A., Mesa, M., Docampo, M. L., Gómez, V. & Pellón, R. F. (2006). Synth. Commun. 36, 271-277.]); Charton et al. (2006[Charton, J., Mizzi, S. G., Fontaine, M. A. D., Foufelle, F., Hainault, I., Espiard, J. G. B., Caignard, D. H. & Sergheraert, C. (2006). Bioorg. Med. Chem. 14, 4490-4518.]). For related structures, see: Du et al. (2009[Du, P., Jiang, X. K. & Li, Z. T. (2009). Tetrahedron Lett. 50, 316-319.]); Qi et al. (2002[Qi, J. Y., Chen, J., Yang, Q. Y., Zhou, Z. Y. & Chan, A. S. C. (2002). Acta Cryst. E58, o1232-o1233.])..

[Scheme 1]

Experimental

Crystal data
  • C20H18N2O

  • Mr = 302.36

  • Orthorhombic, P n a 21

  • a = 26.537 (3) Å

  • b = 17.7337 (19) Å

  • c = 6.8457 (7) Å

  • V = 3221.6 (6) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 93 K

  • 0.50 × 0.40 × 0.33 mm

Data collection
  • Rigaku SPIDER diffractometer

  • Absorption correction: none

  • 21180 measured reflections

  • 3989 independent reflections

  • 3913 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.074

  • S = 1.01

  • 3989 reflections

  • 433 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.20 e Å−3

  • Δρmin = −0.14 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1′—H1′N⋯O1′ 0.86 (2) 1.99 (2) 2.704 (2) 138 (2)
N1—H1N⋯O1 0.94 (2) 2.02 (2) 2.767 (2) 134 (2)
N2′—H2′N⋯O1i 0.90 (2) 1.96 (2) 2.850 (2) 167 (2)
N2—H2N⋯O1′ 0.90 (2) 2.02 (2) 2.921 (2) 173 (2)
C9—H9⋯Cg1ii 0.95 2.79 3.496 (2) 132
C15′—H15′⋯Cg2 0.95 2.95 3.779 (2) 148
C19—H19⋯Cg5iii 0.95 2.79 3.595 (2) 143
C3′—H3′⋯Cg6iv 0.95 2.97 3.933 (2) 175
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) x, y, z-1; (iii) x, y, z+1; (iv) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]. Cg1 is the centroid of ring I (C1–C6), Cg2 is the centroid of ring II (C7–C12), Cg5 is the centroid of ring II′ (C7′–C12′) and Cg6 is the centroid of ring III′ (C14′–C19′)

Data collection: RAPID-AUTO (Rigaku/MSC, 2004[Rigaku/MSC (2004). RAPID-AUTO. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

In the past decade, the assessment of new hydrogen bonding patterns has received great attention due to their potential applications in biological, materials and supramolecular sciences, and crystal engineering. Here we report on the crystal structure of the title compound, a phenyl-amino-benzamide.

The molecular structure of the two independent molecules (A and B) of the title compound are illustrated in Fig. 1. The bond lengths and angles are within normal ranges. The conformation of the two independent molecules is slightly different. The dihedral angles between the central aromatic ring, II (C7—C12 molecule A, C7'-C12' molecule B), and rings I (C1—C6 molecule A, C1'-C6' molecule B) and III (C14—C19 molecule A, C14'-C19' molecule B), are 47.13 (9) and 89.36 (9)°, respectively, for molecule A, and 29.60 (9) and 70.72 (9)°, respectively, for molecule B. Rings I and III are inclined to one another by 86.57 (9)° in molecule A, and 64.59 (10)° in molecule B. The amide unit (N1/C7/O1 molecule A, N1'/C7'/O1' molecule B) lies out of the plane of rings II and III; the dihedral angles being 38.2 (2) and 52.2 (2)°, respectively, in molecule A, and 34.5 (2) and 36.4 (2)°, respectively, in molecule B. The molecular structure of each molecule is stabilized by a N—H···O intramolecular hydrogen bond, involving the amino H-atom and the benzamide carbonyl O-atom (Table 1).

In the crystal structure molecules are linked through N—H···O intermolecular hydrogen bonds, involving the benzamide carbonyl O-atom (O1 and O1') and the 4-methyl-Benzenamine amino H-atoms (H2'N and H2N) of the other molecule (Table 1), so forming chains propagating in direction [010]. In addition a number of C—H···π interactions are observed (Table 1). Footnote to Table 1: Cg1 centroid of ring I (= C1—C6); Cg2 centroid of ring II (= C7—C12); Cg5 centroid of ring II' (= C7'-C12'); Cg6 centroid of ring III' (= C14'-C19').

Related literature top

For the synthesis, see: Martín et al. (2006); Charton et al. (2006). For related structures, see: Du et al. (2009); Qi et al. (2002). Cg1 id the centroid of ring I (C1–C6), Cg2 is the centroid of ring II (C7–C12), Cg5 is the centroid of ring II' (= C7'–C12') and Cg6 is the centroid of ring III' (= C14'–C19').

Experimental top

The title compound was prepared according to the reported procedures (Martín et al., 2006; Charton et al., 2006). Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from dichloromethane.

Refinement top

In the absence of significant anomalous dispersion effects, the Friedel pairs were merged. H atoms were placed in calculated positions, with N—H = 0.88–0.93 Å and C—H = 0.95 Å, and refined in riding mode, with Uiso(H) = 1.2Ueq(c,N).

Computing details top

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO (Rigaku/MSC, 2004); data reduction: RAPID-AUTO (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering. Intra- and inter-molecular N—H···O hydrogen bonds are shown as dashed lines.
3-Anilino-N-p-tolylbenzamide top
Crystal data top
C20H18N2ODx = 1.247 Mg m3
Mr = 302.36Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 10095 reflections
a = 26.537 (3) Åθ = 3.1–27.5°
b = 17.7337 (19) ŵ = 0.08 mm1
c = 6.8457 (7) ÅT = 93 K
V = 3221.6 (6) Å3Block, colorless
Z = 80.50 × 0.40 × 0.33 mm
F(000) = 1280
Data collection top
Rigaku SPIDER
diffractometer
3913 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.028
Graphite monochromatorθmax = 27.5°, θmin = 3.1°
ω scansh = 3425
21180 measured reflectionsk = 2322
3989 independent reflectionsl = 88
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0338P)2 + 0.690P]
where P = (Fo2 + 2Fc2)/3
3989 reflections(Δ/σ)max = 0.001
433 parametersΔρmax = 0.20 e Å3
1 restraintΔρmin = 0.14 e Å3
Crystal data top
C20H18N2OV = 3221.6 (6) Å3
Mr = 302.36Z = 8
Orthorhombic, Pna21Mo Kα radiation
a = 26.537 (3) ŵ = 0.08 mm1
b = 17.7337 (19) ÅT = 93 K
c = 6.8457 (7) Å0.50 × 0.40 × 0.33 mm
Data collection top
Rigaku SPIDER
diffractometer
3913 reflections with I > 2σ(I)
21180 measured reflectionsRint = 0.028
3989 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0341 restraint
wR(F2) = 0.074H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.20 e Å3
3989 reflectionsΔρmin = 0.14 e Å3
433 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
xyzUiso*/Ueq
O10.25647 (5)0.51964 (7)0.6647 (2)0.0269 (3)
N10.15605 (6)0.48341 (9)0.6089 (3)0.0241 (3)
N20.30182 (5)0.41608 (8)0.5815 (2)0.0215 (3)
C10.09231 (7)0.52823 (9)0.8280 (3)0.0243 (4)
H10.11180.57250.84770.029*
C20.04777 (7)0.51875 (10)0.9296 (3)0.0287 (4)
H20.03690.55671.01810.034*
C30.01864 (7)0.45450 (11)0.9040 (3)0.0294 (4)
H30.01210.44820.97360.035*
C40.03524 (7)0.39970 (10)0.7750 (3)0.0270 (4)
H40.01570.35530.75700.032*
C50.07986 (7)0.40848 (10)0.6713 (3)0.0233 (4)
H50.09060.37030.58320.028*
C60.10904 (6)0.47343 (9)0.6968 (3)0.0212 (4)
C70.17326 (6)0.45206 (9)0.4353 (3)0.0199 (4)
C80.14034 (7)0.43026 (9)0.2865 (3)0.0239 (4)
H80.10510.43680.30360.029*
C90.15820 (7)0.39937 (10)0.1154 (3)0.0269 (4)
H90.13500.38390.01750.032*
C100.20968 (7)0.39049 (11)0.0835 (3)0.0275 (4)
H100.22180.36990.03570.033*
C110.24272 (7)0.41228 (9)0.2290 (3)0.0232 (4)
H110.27790.40680.20830.028*
C120.22564 (6)0.44210 (9)0.4052 (3)0.0202 (4)
C130.26208 (6)0.46334 (9)0.5607 (3)0.0202 (4)
C140.34212 (6)0.42888 (9)0.7153 (3)0.0213 (4)
C150.36702 (7)0.49770 (10)0.7182 (3)0.0274 (4)
H150.35650.53720.63370.033*
C160.40720 (7)0.50894 (10)0.8440 (3)0.0290 (4)
H160.42390.55630.84500.035*
C170.42351 (7)0.45242 (11)0.9681 (3)0.0295 (4)
C180.39818 (8)0.38430 (11)0.9620 (4)0.0389 (5)
H180.40880.34471.04590.047*
C190.35778 (8)0.37202 (10)0.8374 (3)0.0320 (5)
H190.34110.32460.83650.038*
C200.46697 (9)0.46438 (13)1.1061 (4)0.0473 (6)
H20A0.45530.49251.22080.057*
H20B0.49350.49301.03980.057*
H20C0.48030.41541.14750.057*
O1'0.30100 (5)0.26650 (6)0.4028 (2)0.0237 (3)
N1'0.39641 (5)0.23148 (8)0.2976 (2)0.0224 (3)
N2'0.25027 (5)0.16713 (8)0.3282 (2)0.0216 (3)
C1'0.45616 (7)0.30174 (10)0.4848 (3)0.0284 (4)
H1'0.42870.32870.54010.034*
C2'0.50487 (8)0.31826 (11)0.5432 (4)0.0360 (5)
H2'0.51050.35580.63970.043*
C3'0.54540 (7)0.28053 (11)0.4622 (4)0.0346 (5)
H3'0.57890.29320.49880.041*
C4'0.53645 (7)0.22427 (11)0.3276 (3)0.0301 (4)
H4'0.56420.19790.27240.036*
C5'0.48774 (7)0.20532 (10)0.2708 (3)0.0238 (4)
H5'0.48230.16500.18200.029*
C6'0.44695 (6)0.24589 (9)0.3451 (3)0.0210 (4)
C7'0.37496 (6)0.20358 (9)0.1275 (3)0.0196 (4)
C8'0.40260 (7)0.18644 (10)0.0417 (3)0.0234 (4)
H8'0.43800.19470.04320.028*
C9'0.37921 (7)0.15781 (10)0.2062 (3)0.0262 (4)
H9'0.39880.14620.31830.031*
C10'0.32753 (7)0.14578 (10)0.2102 (3)0.0255 (4)
H10'0.31170.12540.32300.031*
C11'0.29945 (7)0.16400 (9)0.0466 (3)0.0219 (4)
H11'0.26400.15710.04940.026*
C12'0.32198 (6)0.19223 (9)0.1227 (3)0.0195 (3)
C13'0.29056 (6)0.21259 (9)0.2951 (3)0.0200 (3)
C14'0.21651 (6)0.17360 (9)0.4875 (3)0.0206 (4)
C15'0.20087 (6)0.24292 (10)0.5599 (3)0.0239 (4)
H15'0.21270.28830.50240.029*
C16'0.16781 (7)0.24530 (10)0.7170 (3)0.0258 (4)
H16'0.15790.29290.76780.031*
C17'0.14875 (7)0.18014 (11)0.8023 (3)0.0272 (4)
C18'0.16414 (7)0.11125 (10)0.7252 (3)0.0293 (4)
H18'0.15140.06580.77980.035*
C19'0.19773 (7)0.10764 (10)0.5704 (3)0.0264 (4)
H19'0.20800.06000.52070.032*
C20'0.11217 (8)0.18513 (13)0.9705 (4)0.0395 (5)
H20D0.08960.22820.95070.047*
H20E0.13090.19181.09270.047*
H20F0.09230.13860.97730.047*
H1N0.1801 (9)0.5147 (13)0.670 (4)0.046 (7)*
H2N0.2992 (7)0.3714 (12)0.521 (4)0.032 (6)*
H1'N0.3754 (8)0.2536 (12)0.375 (4)0.033 (6)*
H2'N0.2491 (8)0.1238 (12)0.259 (4)0.034 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0280 (7)0.0196 (6)0.0332 (8)0.0032 (5)0.0046 (6)0.0098 (6)
N10.0214 (7)0.0261 (7)0.0248 (8)0.0018 (6)0.0004 (7)0.0075 (7)
N20.0237 (7)0.0163 (6)0.0244 (8)0.0026 (5)0.0035 (6)0.0065 (6)
C10.0310 (9)0.0185 (8)0.0235 (10)0.0024 (7)0.0001 (8)0.0004 (8)
C20.0353 (10)0.0254 (9)0.0253 (11)0.0066 (7)0.0054 (9)0.0008 (8)
C30.0280 (10)0.0323 (10)0.0280 (11)0.0030 (7)0.0043 (8)0.0078 (9)
C40.0271 (9)0.0262 (9)0.0276 (10)0.0016 (7)0.0042 (8)0.0052 (8)
C50.0266 (9)0.0220 (8)0.0213 (9)0.0031 (7)0.0062 (8)0.0004 (7)
C60.0225 (8)0.0217 (8)0.0193 (9)0.0042 (6)0.0022 (7)0.0026 (7)
C70.0250 (9)0.0163 (7)0.0185 (9)0.0015 (6)0.0016 (7)0.0007 (7)
C80.0253 (9)0.0222 (8)0.0240 (10)0.0015 (7)0.0037 (8)0.0006 (8)
C90.0322 (10)0.0284 (9)0.0202 (10)0.0009 (7)0.0070 (8)0.0011 (8)
C100.0348 (10)0.0312 (9)0.0166 (9)0.0002 (8)0.0003 (8)0.0022 (8)
C110.0255 (9)0.0207 (8)0.0234 (10)0.0003 (7)0.0010 (7)0.0004 (8)
C120.0243 (8)0.0155 (7)0.0207 (9)0.0008 (6)0.0014 (7)0.0001 (7)
C130.0234 (9)0.0163 (7)0.0209 (10)0.0006 (6)0.0019 (7)0.0011 (7)
C140.0211 (8)0.0216 (8)0.0213 (9)0.0005 (6)0.0002 (7)0.0055 (7)
C150.0290 (9)0.0240 (8)0.0293 (10)0.0037 (7)0.0030 (8)0.0053 (8)
C160.0301 (10)0.0253 (9)0.0315 (11)0.0075 (7)0.0050 (9)0.0015 (8)
C170.0285 (10)0.0307 (9)0.0294 (11)0.0047 (7)0.0072 (9)0.0015 (9)
C180.0449 (12)0.0287 (9)0.0432 (13)0.0063 (8)0.0204 (11)0.0112 (10)
C190.0377 (11)0.0210 (9)0.0374 (12)0.0057 (7)0.0112 (10)0.0036 (9)
C200.0502 (14)0.0425 (12)0.0491 (15)0.0142 (10)0.0256 (12)0.0115 (12)
O1'0.0238 (6)0.0183 (5)0.0290 (7)0.0007 (5)0.0005 (6)0.0077 (6)
N1'0.0191 (7)0.0266 (7)0.0215 (8)0.0003 (6)0.0005 (7)0.0053 (7)
N2'0.0233 (7)0.0163 (7)0.0251 (8)0.0018 (5)0.0032 (7)0.0063 (6)
C1'0.0297 (10)0.0246 (9)0.0308 (11)0.0007 (7)0.0049 (9)0.0021 (9)
C2'0.0394 (12)0.0288 (10)0.0397 (12)0.0048 (8)0.0155 (10)0.0016 (9)
C3'0.0257 (10)0.0350 (10)0.0430 (13)0.0077 (8)0.0128 (10)0.0125 (10)
C4'0.0227 (9)0.0360 (10)0.0317 (11)0.0035 (7)0.0014 (8)0.0141 (9)
C5'0.0258 (9)0.0229 (8)0.0227 (9)0.0014 (7)0.0009 (8)0.0043 (8)
C6'0.0217 (8)0.0202 (8)0.0212 (9)0.0025 (6)0.0008 (7)0.0042 (7)
C7'0.0232 (8)0.0167 (7)0.0190 (9)0.0001 (6)0.0019 (7)0.0011 (7)
C8'0.0234 (9)0.0259 (8)0.0209 (9)0.0008 (7)0.0008 (7)0.0015 (8)
C9'0.0303 (9)0.0305 (9)0.0177 (9)0.0030 (7)0.0034 (8)0.0002 (8)
C10'0.0321 (10)0.0252 (8)0.0191 (9)0.0006 (7)0.0036 (8)0.0007 (8)
C11'0.0235 (8)0.0199 (8)0.0223 (10)0.0005 (6)0.0026 (7)0.0010 (7)
C12'0.0230 (8)0.0143 (7)0.0213 (9)0.0007 (6)0.0006 (7)0.0003 (7)
C13'0.0206 (8)0.0166 (7)0.0228 (9)0.0022 (6)0.0027 (7)0.0006 (7)
C14'0.0187 (8)0.0220 (8)0.0209 (9)0.0007 (6)0.0015 (7)0.0049 (7)
C15'0.0215 (9)0.0211 (8)0.0292 (11)0.0007 (6)0.0002 (8)0.0042 (8)
C16'0.0248 (9)0.0243 (8)0.0283 (10)0.0048 (7)0.0020 (8)0.0091 (8)
C17'0.0269 (9)0.0340 (9)0.0208 (10)0.0084 (7)0.0008 (8)0.0011 (9)
C18'0.0339 (10)0.0279 (9)0.0262 (10)0.0027 (7)0.0050 (9)0.0022 (8)
C19'0.0305 (10)0.0219 (8)0.0268 (11)0.0018 (7)0.0019 (8)0.0044 (8)
C20'0.0448 (12)0.0427 (12)0.0309 (12)0.0139 (9)0.0115 (11)0.0019 (10)
Geometric parameters (Å, º) top
O1—C131.235 (2)O1'—C13'1.239 (2)
N1—C71.389 (2)N1'—C7'1.388 (2)
N1—C61.396 (2)N1'—C6'1.404 (2)
N1—H1N0.94 (2)N1'—H1'N0.86 (2)
N2—C131.354 (2)N2'—C13'1.358 (2)
N2—C141.426 (2)N2'—C14'1.416 (2)
N2—H2N0.90 (2)N2'—H2'N0.90 (2)
C1—C21.381 (3)C1'—C2'1.385 (3)
C1—C61.396 (2)C1'—C6'1.398 (3)
C1—H10.9500C1'—H1'0.9500
C2—C31.388 (3)C2'—C3'1.383 (3)
C2—H20.9500C2'—H2'0.9500
C3—C41.385 (3)C3'—C4'1.379 (3)
C3—H30.9500C3'—H3'0.9500
C4—C51.389 (3)C4'—C5'1.391 (3)
C4—H40.9500C4'—H4'0.9500
C5—C61.399 (2)C5'—C6'1.396 (2)
C5—H50.9500C5'—H5'0.9500
C7—C81.396 (2)C7'—C8'1.404 (3)
C7—C121.416 (2)C7'—C12'1.420 (2)
C8—C91.378 (3)C8'—C9'1.382 (3)
C8—H80.9500C8'—H8'0.9500
C9—C101.392 (3)C9'—C10'1.388 (3)
C9—H90.9500C9'—H9'0.9500
C10—C111.382 (3)C10'—C11'1.383 (3)
C10—H100.9500C10'—H10'0.9500
C11—C121.393 (3)C11'—C12'1.397 (3)
C11—H110.9500C11'—H11'0.9500
C12—C131.487 (2)C12'—C13'1.490 (3)
C14—C191.374 (3)C14'—C15'1.389 (2)
C14—C151.388 (2)C14'—C19'1.392 (2)
C15—C161.385 (3)C15'—C16'1.389 (3)
C15—H150.9500C15'—H15'0.9500
C16—C171.384 (3)C16'—C17'1.390 (3)
C16—H160.9500C16'—H16'0.9500
C17—C181.383 (3)C17'—C18'1.392 (3)
C17—C201.506 (3)C17'—C20'1.508 (3)
C18—C191.387 (3)C18'—C19'1.386 (3)
C18—H180.9500C18'—H18'0.9500
C19—H190.9500C19'—H19'0.9500
C20—H20A0.9800C20'—H20D0.9800
C20—H20B0.9800C20'—H20E0.9800
C20—H20C0.9800C20'—H20F0.9800
C7—N1—C6127.70 (16)C7'—N1'—C6'130.64 (16)
C7—N1—H1N113.2 (16)C7'—N1'—H1'N114.4 (16)
C6—N1—H1N119.1 (16)C6'—N1'—H1'N113.0 (15)
C13—N2—C14123.56 (15)C13'—N2'—C14'125.34 (16)
C13—N2—H2N116.0 (13)C13'—N2'—H2'N116.4 (14)
C14—N2—H2N119.7 (13)C14'—N2'—H2'N116.8 (14)
C2—C1—C6120.75 (17)C2'—C1'—C6'120.72 (19)
C2—C1—H1119.6C2'—C1'—H1'119.6
C6—C1—H1119.6C6'—C1'—H1'119.6
C1—C2—C3120.87 (18)C3'—C2'—C1'120.5 (2)
C1—C2—H2119.6C3'—C2'—H2'119.7
C3—C2—H2119.6C1'—C2'—H2'119.7
C4—C3—C2118.63 (18)C4'—C3'—C2'118.95 (18)
C4—C3—H3120.7C4'—C3'—H3'120.5
C2—C3—H3120.7C2'—C3'—H3'120.5
C3—C4—C5121.21 (17)C3'—C4'—C5'121.45 (19)
C3—C4—H4119.4C3'—C4'—H4'119.3
C5—C4—H4119.4C5'—C4'—H4'119.3
C4—C5—C6120.04 (17)C4'—C5'—C6'119.63 (18)
C4—C5—H5120.0C4'—C5'—H5'120.2
C6—C5—H5120.0C6'—C5'—H5'120.2
C1—C6—N1118.24 (16)C5'—C6'—C1'118.60 (17)
C1—C6—C5118.50 (17)C5'—C6'—N1'124.26 (16)
N1—C6—C5123.05 (16)C1'—C6'—N1'117.03 (16)
N1—C7—C8121.94 (16)N1'—C7'—C8'123.72 (16)
N1—C7—C12119.79 (16)N1'—C7'—C12'118.43 (16)
C8—C7—C12118.27 (16)C8'—C7'—C12'117.85 (16)
C9—C8—C7120.99 (17)C9'—C8'—C7'121.12 (16)
C9—C8—H8119.5C9'—C8'—H8'119.4
C7—C8—H8119.5C7'—C8'—H8'119.4
C8—C9—C10121.07 (18)C8'—C9'—C10'121.06 (18)
C8—C9—H9119.5C8'—C9'—H9'119.5
C10—C9—H9119.5C10'—C9'—H9'119.5
C11—C10—C9118.54 (18)C11'—C10'—C9'118.70 (18)
C11—C10—H10120.7C11'—C10'—H10'120.7
C9—C10—H10120.7C9'—C10'—H10'120.7
C10—C11—C12121.60 (17)C10'—C11'—C12'121.66 (16)
C10—C11—H11119.2C10'—C11'—H11'119.2
C12—C11—H11119.2C12'—C11'—H11'119.2
C11—C12—C7119.51 (16)C11'—C12'—C7'119.58 (17)
C11—C12—C13120.31 (16)C11'—C12'—C13'120.30 (15)
C7—C12—C13120.19 (16)C7'—C12'—C13'120.08 (16)
O1—C13—N2122.23 (16)O1'—C13'—N2'122.34 (17)
O1—C13—C12122.61 (15)O1'—C13'—C12'122.24 (15)
N2—C13—C12115.15 (15)N2'—C13'—C12'115.41 (15)
C19—C14—C15119.51 (17)C15'—C14'—C19'119.43 (17)
C19—C14—N2120.05 (16)C15'—C14'—N2'122.37 (16)
C15—C14—N2120.39 (17)C19'—C14'—N2'118.18 (15)
C16—C15—C14120.12 (18)C16'—C15'—C14'119.47 (17)
C16—C15—H15119.9C16'—C15'—H15'120.3
C14—C15—H15119.9C14'—C15'—H15'120.3
C17—C16—C15121.23 (17)C15'—C16'—C17'122.00 (17)
C17—C16—H16119.4C15'—C16'—H16'119.0
C15—C16—H16119.4C17'—C16'—H16'119.0
C18—C17—C16117.53 (18)C16'—C17'—C18'117.62 (18)
C18—C17—C20120.94 (19)C16'—C17'—C20'120.39 (17)
C16—C17—C20121.53 (17)C18'—C17'—C20'121.99 (18)
C17—C18—C19122.09 (19)C19'—C18'—C17'121.27 (18)
C17—C18—H18119.0C19'—C18'—H18'119.4
C19—C18—H18119.0C17'—C18'—H18'119.4
C14—C19—C18119.51 (17)C18'—C19'—C14'120.18 (17)
C14—C19—H19120.2C18'—C19'—H19'119.9
C18—C19—H19120.2C14'—C19'—H19'119.9
C17—C20—H20A109.5C17'—C20'—H20D109.5
C17—C20—H20B109.5C17'—C20'—H20E109.5
H20A—C20—H20B109.5H20D—C20'—H20E109.5
C17—C20—H20C109.5C17'—C20'—H20F109.5
H20A—C20—H20C109.5H20D—C20'—H20F109.5
H20B—C20—H20C109.5H20E—C20'—H20F109.5
C6—C1—C2—C30.1 (3)C6'—C1'—C2'—C3'1.0 (3)
C1—C2—C3—C40.3 (3)C1'—C2'—C3'—C4'2.4 (3)
C2—C3—C4—C50.5 (3)C2'—C3'—C4'—C5'0.5 (3)
C3—C4—C5—C60.2 (3)C3'—C4'—C5'—C6'2.6 (3)
C2—C1—C6—N1175.43 (18)C4'—C5'—C6'—C1'3.9 (3)
C2—C1—C6—C50.4 (3)C4'—C5'—C6'—N1'179.98 (17)
C7—N1—C6—C1157.58 (17)C2'—C1'—C6'—C5'2.2 (3)
C7—N1—C6—C527.7 (3)C2'—C1'—C6'—N1'178.51 (18)
C4—C5—C6—C10.2 (3)C7'—N1'—C6'—C5'30.9 (3)
C4—C5—C6—N1175.00 (18)C7'—N1'—C6'—C1'153.02 (18)
C6—N1—C7—C826.0 (3)C6'—N1'—C7'—C8'2.7 (3)
C6—N1—C7—C12154.54 (17)C6'—N1'—C7'—C12'177.90 (16)
N1—C7—C8—C9179.91 (16)N1'—C7'—C8'—C9'179.14 (16)
C12—C7—C8—C90.4 (3)C12'—C7'—C8'—C9'1.5 (3)
C7—C8—C9—C101.5 (3)C7'—C8'—C9'—C10'0.7 (3)
C8—C9—C10—C111.0 (3)C8'—C9'—C10'—C11'0.9 (3)
C9—C10—C11—C120.4 (3)C9'—C10'—C11'—C12'1.6 (3)
C10—C11—C12—C71.4 (3)C10'—C11'—C12'—C7'0.8 (3)
C10—C11—C12—C13178.56 (16)C10'—C11'—C12'—C13'178.90 (15)
N1—C7—C12—C11178.50 (15)N1'—C7'—C12'—C11'179.82 (15)
C8—C7—C12—C111.0 (2)C8'—C7'—C12'—C11'0.8 (2)
N1—C7—C12—C131.5 (2)N1'—C7'—C12'—C13'2.1 (2)
C8—C7—C12—C13179.01 (15)C8'—C7'—C12'—C13'177.37 (15)
C14—N2—C13—O13.9 (3)C14'—N2'—C13'—O1'1.7 (3)
C14—N2—C13—C12176.59 (16)C14'—N2'—C13'—C12'177.13 (15)
C11—C12—C13—O1142.03 (18)C11'—C12'—C13'—O1'144.84 (17)
C7—C12—C13—O138.0 (2)C7'—C12'—C13'—O1'33.3 (2)
C11—C12—C13—N238.5 (2)C11'—C12'—C13'—N2'36.4 (2)
C7—C12—C13—N2141.49 (17)C7'—C12'—C13'—N2'145.52 (16)
C13—N2—C14—C19131.4 (2)C13'—N2'—C14'—C15'38.3 (3)
C13—N2—C14—C1551.1 (3)C13'—N2'—C14'—C19'143.13 (18)
C19—C14—C15—C160.3 (3)C19'—C14'—C15'—C16'1.7 (3)
N2—C14—C15—C16177.87 (17)N2'—C14'—C15'—C16'179.80 (16)
C14—C15—C16—C170.3 (3)C14'—C15'—C16'—C17'1.5 (3)
C15—C16—C17—C180.1 (3)C15'—C16'—C17'—C18'0.3 (3)
C15—C16—C17—C20179.6 (2)C15'—C16'—C17'—C20'178.89 (18)
C16—C17—C18—C190.1 (4)C16'—C17'—C18'—C19'0.7 (3)
C20—C17—C18—C19179.5 (2)C20'—C17'—C18'—C19'179.91 (19)
C15—C14—C19—C180.1 (3)C17'—C18'—C19'—C14'0.5 (3)
N2—C14—C19—C18177.73 (19)C15'—C14'—C19'—C18'0.7 (3)
C17—C18—C19—C140.0 (4)N2'—C14'—C19'—C18'179.27 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.86 (2)1.99 (2)2.704 (2)138 (2)
N1—H1N···O10.94 (2)2.02 (2)2.767 (2)134 (2)
N2—H2N···O1i0.90 (2)1.96 (2)2.850 (2)167 (2)
N2—H2N···O10.90 (2)2.02 (2)2.921 (2)173 (2)
C9—H9···Cg1ii0.952.793.496 (2)132
C15—H15···Cg20.952.953.779 (2)148
C19—H19···Cg5iii0.952.793.595 (2)143
C3—H3···Cg6iv0.952.973.933 (2)175
Symmetry codes: (i) x+1/2, y1/2, z1/2; (ii) x, y, z1; (iii) x, y, z+1; (iv) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC20H18N2O
Mr302.36
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)93
a, b, c (Å)26.537 (3), 17.7337 (19), 6.8457 (7)
V3)3221.6 (6)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.50 × 0.40 × 0.33
Data collection
DiffractometerRigaku SPIDER
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
21180, 3989, 3913
Rint0.028
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.074, 1.01
No. of reflections3989
No. of parameters433
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.20, 0.14

Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1'—H1'N···O1'0.86 (2)1.99 (2)2.704 (2)138 (2)
N1—H1N···O10.94 (2)2.02 (2)2.767 (2)134 (2)
N2'—H2'N···O1i0.90 (2)1.96 (2)2.850 (2)167 (2)
N2—H2N···O1'0.90 (2)2.02 (2)2.921 (2)173 (2)
C9—H9···Cg1ii0.952.793.496 (2)132
C15'—H15'···Cg20.952.953.779 (2)148
C19—H19···Cg5iii0.952.793.595 (2)143
C3'—H3'···Cg6iv0.952.973.933 (2)175
Symmetry codes: (i) x+1/2, y1/2, z1/2; (ii) x, y, z1; (iii) x, y, z+1; (iv) x+1/2, y+1/2, z.
 

Acknowledgements

The authors thank the Scientific Researching Fund Projects of China West Normal University (grant No. 06B003) and the Youth Fund Projects of Sichuan Educational Department (grant No. 2006B039).

References

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First citationDu, P., Jiang, X. K. & Li, Z. T. (2009). Tetrahedron Lett. 50, 316–319.  Web of Science CSD CrossRef CAS
First citationMartín, A., Mesa, M., Docampo, M. L., Gómez, V. & Pellón, R. F. (2006). Synth. Commun. 36, 271–277.
First citationQi, J. Y., Chen, J., Yang, Q. Y., Zhou, Z. Y. & Chan, A. S. C. (2002). Acta Cryst. E58, o1232–o1233.  Web of Science CSD CrossRef IUCr Journals
First citationRigaku/MSC (2004). RAPID-AUTO. Rigaku/MSC Inc., The Woodlands, Texas, USA.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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