3-Anilino-N-p-tolyl­benzamide

Yang, X.-X.; Liu, G.-F.; Qin, D.-B.

doi:10.1107/S1600536809049939

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o116

doi:10.1107/S1600536809049939

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3-Anilino-N-p-tolylbenzamide

Xing-Xing Yang,^a Guan-Feng Liu ^a and Da-Bin Qin ^a ^*

^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 ); Charton et al. (2006 ). For related structures, see: Du et al. (2009 ); Qi et al. (2002 )..

Experimental

Crystal data

C₂₀H₁₈N₂O
M_r = 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)
R_int = 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
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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′⋯Cg6^iv	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 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049939/su2143sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049939/su2143Isup2.hkl

checkCIF report

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.

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

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

C₂₀H₁₈N₂O	D_x = 1.247 Mg m⁻³
M_r = 302.36	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 10095 reflections
a = 26.537 (3) Å	θ = 3.1–27.5°
b = 17.7337 (19) Å	µ = 0.08 mm⁻¹
c = 6.8457 (7) Å	T = 93 K
V = 3221.6 (6) Å³	Block, colorless
Z = 8	0.50 × 0.40 × 0.33 mm
F(000) = 1280

Data collection top

Rigaku SPIDER diffractometer	3913 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.028
Graphite monochromator	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −34→25
21180 measured reflections	k = −23→22
3989 independent reflections	l = −8→8

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0338P)² + 0.690P] where P = (F_o² + 2F_c²)/3
3989 reflections	(Δ/σ)_max = 0.001
433 parameters	Δρ_max = 0.20 e Å⁻³
1 restraint	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₂₀H₁₈N₂O	V = 3221.6 (6) Å³
M_r = 302.36	Z = 8
Orthorhombic, Pna2₁	Mo Kα radiation
a = 26.537 (3) Å	µ = 0.08 mm⁻¹
b = 17.7337 (19) Å	T = 93 K
c = 6.8457 (7) Å	0.50 × 0.40 × 0.33 mm

Data collection top

Rigaku SPIDER diffractometer	3913 reflections with I > 2σ(I)
21180 measured reflections	R_int = 0.028
3989 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	1 restraint
wR(F²) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.20 e Å⁻³
3989 reflections	Δρ_min = −0.14 e Å⁻³
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

	x	y	z	U_iso*/U_eq
O1	0.25647 (5)	0.51964 (7)	0.6647 (2)	0.0269 (3)
N1	0.15605 (6)	0.48341 (9)	0.6089 (3)	0.0241 (3)
N2	0.30182 (5)	0.41608 (8)	0.5815 (2)	0.0215 (3)
C1	0.09231 (7)	0.52823 (9)	0.8280 (3)	0.0243 (4)
H1	0.1118	0.5725	0.8477	0.029*
C2	0.04777 (7)	0.51875 (10)	0.9296 (3)	0.0287 (4)
H2	0.0369	0.5567	1.0181	0.034*
C3	0.01864 (7)	0.45450 (11)	0.9040 (3)	0.0294 (4)
H3	−0.0121	0.4482	0.9736	0.035*
C4	0.03524 (7)	0.39970 (10)	0.7750 (3)	0.0270 (4)
H4	0.0157	0.3553	0.7570	0.032*
C5	0.07986 (7)	0.40848 (10)	0.6713 (3)	0.0233 (4)
H5	0.0906	0.3703	0.5832	0.028*
C6	0.10904 (6)	0.47343 (9)	0.6968 (3)	0.0212 (4)
C7	0.17326 (6)	0.45206 (9)	0.4353 (3)	0.0199 (4)
C8	0.14034 (7)	0.43026 (9)	0.2865 (3)	0.0239 (4)
H8	0.1051	0.4368	0.3036	0.029*
C9	0.15820 (7)	0.39937 (10)	0.1154 (3)	0.0269 (4)
H9	0.1350	0.3839	0.0175	0.032*
C10	0.20968 (7)	0.39049 (11)	0.0835 (3)	0.0275 (4)
H10	0.2218	0.3699	−0.0357	0.033*
C11	0.24272 (7)	0.41228 (9)	0.2290 (3)	0.0232 (4)
H11	0.2779	0.4068	0.2083	0.028*
C12	0.22564 (6)	0.44210 (9)	0.4052 (3)	0.0202 (4)
C13	0.26208 (6)	0.46334 (9)	0.5607 (3)	0.0202 (4)
C14	0.34212 (6)	0.42888 (9)	0.7153 (3)	0.0213 (4)
C15	0.36702 (7)	0.49770 (10)	0.7182 (3)	0.0274 (4)
H15	0.3565	0.5372	0.6337	0.033*
C16	0.40720 (7)	0.50894 (10)	0.8440 (3)	0.0290 (4)
H16	0.4239	0.5563	0.8450	0.035*
C17	0.42351 (7)	0.45242 (11)	0.9681 (3)	0.0295 (4)
C18	0.39818 (8)	0.38430 (11)	0.9620 (4)	0.0389 (5)
H18	0.4088	0.3447	1.0459	0.047*
C19	0.35778 (8)	0.37202 (10)	0.8374 (3)	0.0320 (5)
H19	0.3411	0.3246	0.8365	0.038*
C20	0.46697 (9)	0.46438 (13)	1.1061 (4)	0.0473 (6)
H20A	0.4553	0.4925	1.2208	0.057*
H20B	0.4935	0.4930	1.0398	0.057*
H20C	0.4803	0.4154	1.1475	0.057*
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'	0.4287	0.3287	0.5401	0.034*
C2'	0.50487 (8)	0.31826 (11)	0.5432 (4)	0.0360 (5)
H2'	0.5105	0.3558	0.6397	0.043*
C3'	0.54540 (7)	0.28053 (11)	0.4622 (4)	0.0346 (5)
H3'	0.5789	0.2932	0.4988	0.041*
C4'	0.53645 (7)	0.22427 (11)	0.3276 (3)	0.0301 (4)
H4'	0.5642	0.1979	0.2724	0.036*
C5'	0.48774 (7)	0.20532 (10)	0.2708 (3)	0.0238 (4)
H5'	0.4823	0.1650	0.1820	0.029*
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'	0.4380	0.1947	−0.0432	0.028*
C9'	0.37921 (7)	0.15781 (10)	−0.2062 (3)	0.0262 (4)
H9'	0.3988	0.1462	−0.3183	0.031*
C10'	0.32753 (7)	0.14578 (10)	−0.2102 (3)	0.0255 (4)
H10'	0.3117	0.1254	−0.3230	0.031*
C11'	0.29945 (7)	0.16400 (9)	−0.0466 (3)	0.0219 (4)
H11'	0.2640	0.1571	−0.0494	0.026*
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'	0.2127	0.2883	0.5024	0.029*
C16'	0.16781 (7)	0.24530 (10)	0.7170 (3)	0.0258 (4)
H16'	0.1579	0.2929	0.7678	0.031*
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'	0.1514	0.0658	0.7798	0.035*
C19'	0.19773 (7)	0.10764 (10)	0.5704 (3)	0.0264 (4)
H19'	0.2080	0.0600	0.5207	0.032*
C20'	0.11217 (8)	0.18513 (13)	0.9705 (4)	0.0395 (5)
H20D	0.0896	0.2282	0.9507	0.047*
H20E	0.1309	0.1918	1.0927	0.047*
H20F	0.0923	0.1386	0.9773	0.047*
H1N	0.1801 (9)	0.5147 (13)	0.670 (4)	0.046 (7)*
H2N	0.2992 (7)	0.3714 (12)	0.521 (4)	0.032 (6)*
H1'N	0.3754 (8)	0.2536 (12)	0.375 (4)	0.033 (6)*
H2'N	0.2491 (8)	0.1238 (12)	0.259 (4)	0.034 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0280 (7)	0.0196 (6)	0.0332 (8)	0.0032 (5)	−0.0046 (6)	−0.0098 (6)
N1	0.0214 (7)	0.0261 (7)	0.0248 (8)	−0.0018 (6)	0.0004 (7)	−0.0075 (7)
N2	0.0237 (7)	0.0163 (6)	0.0244 (8)	0.0026 (5)	−0.0035 (6)	−0.0065 (6)
C1	0.0310 (9)	0.0185 (8)	0.0235 (10)	0.0024 (7)	−0.0001 (8)	0.0004 (8)
C2	0.0353 (10)	0.0254 (9)	0.0253 (11)	0.0066 (7)	0.0054 (9)	0.0008 (8)
C3	0.0280 (10)	0.0323 (10)	0.0280 (11)	0.0030 (7)	0.0043 (8)	0.0078 (9)
C4	0.0271 (9)	0.0262 (9)	0.0276 (10)	−0.0016 (7)	−0.0042 (8)	0.0052 (8)
C5	0.0266 (9)	0.0220 (8)	0.0213 (9)	0.0031 (7)	−0.0062 (8)	0.0004 (7)
C6	0.0225 (8)	0.0217 (8)	0.0193 (9)	0.0042 (6)	−0.0022 (7)	0.0026 (7)
C7	0.0250 (9)	0.0163 (7)	0.0185 (9)	0.0015 (6)	−0.0016 (7)	0.0007 (7)
C8	0.0253 (9)	0.0222 (8)	0.0240 (10)	0.0015 (7)	−0.0037 (8)	0.0006 (8)
C9	0.0322 (10)	0.0284 (9)	0.0202 (10)	−0.0009 (7)	−0.0070 (8)	0.0011 (8)
C10	0.0348 (10)	0.0312 (9)	0.0166 (9)	−0.0002 (8)	0.0003 (8)	−0.0022 (8)
C11	0.0255 (9)	0.0207 (8)	0.0234 (10)	0.0003 (7)	0.0010 (7)	−0.0004 (8)
C12	0.0243 (8)	0.0155 (7)	0.0207 (9)	0.0008 (6)	−0.0014 (7)	−0.0001 (7)
C13	0.0234 (9)	0.0163 (7)	0.0209 (10)	−0.0006 (6)	0.0019 (7)	−0.0011 (7)
C14	0.0211 (8)	0.0216 (8)	0.0213 (9)	0.0005 (6)	−0.0002 (7)	−0.0055 (7)
C15	0.0290 (9)	0.0240 (8)	0.0293 (10)	−0.0037 (7)	−0.0030 (8)	0.0053 (8)
C16	0.0301 (10)	0.0253 (9)	0.0315 (11)	−0.0075 (7)	−0.0050 (9)	0.0015 (8)
C17	0.0285 (10)	0.0307 (9)	0.0294 (11)	−0.0047 (7)	−0.0072 (9)	0.0015 (9)
C18	0.0449 (12)	0.0287 (9)	0.0432 (13)	−0.0063 (8)	−0.0204 (11)	0.0112 (10)
C19	0.0377 (11)	0.0210 (9)	0.0374 (12)	−0.0057 (7)	−0.0112 (10)	0.0036 (9)
C20	0.0502 (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—C13	1.235 (2)	O1'—C13'	1.239 (2)
N1—C7	1.389 (2)	N1'—C7'	1.388 (2)
N1—C6	1.396 (2)	N1'—C6'	1.404 (2)
N1—H1N	0.94 (2)	N1'—H1'N	0.86 (2)
N2—C13	1.354 (2)	N2'—C13'	1.358 (2)
N2—C14	1.426 (2)	N2'—C14'	1.416 (2)
N2—H2N	0.90 (2)	N2'—H2'N	0.90 (2)
C1—C2	1.381 (3)	C1'—C2'	1.385 (3)
C1—C6	1.396 (2)	C1'—C6'	1.398 (3)
C1—H1	0.9500	C1'—H1'	0.9500
C2—C3	1.388 (3)	C2'—C3'	1.383 (3)
C2—H2	0.9500	C2'—H2'	0.9500
C3—C4	1.385 (3)	C3'—C4'	1.379 (3)
C3—H3	0.9500	C3'—H3'	0.9500
C4—C5	1.389 (3)	C4'—C5'	1.391 (3)
C4—H4	0.9500	C4'—H4'	0.9500
C5—C6	1.399 (2)	C5'—C6'	1.396 (2)
C5—H5	0.9500	C5'—H5'	0.9500
C7—C8	1.396 (2)	C7'—C8'	1.404 (3)
C7—C12	1.416 (2)	C7'—C12'	1.420 (2)
C8—C9	1.378 (3)	C8'—C9'	1.382 (3)
C8—H8	0.9500	C8'—H8'	0.9500
C9—C10	1.392 (3)	C9'—C10'	1.388 (3)
C9—H9	0.9500	C9'—H9'	0.9500
C10—C11	1.382 (3)	C10'—C11'	1.383 (3)
C10—H10	0.9500	C10'—H10'	0.9500
C11—C12	1.393 (3)	C11'—C12'	1.397 (3)
C11—H11	0.9500	C11'—H11'	0.9500
C12—C13	1.487 (2)	C12'—C13'	1.490 (3)
C14—C19	1.374 (3)	C14'—C15'	1.389 (2)
C14—C15	1.388 (2)	C14'—C19'	1.392 (2)
C15—C16	1.385 (3)	C15'—C16'	1.389 (3)
C15—H15	0.9500	C15'—H15'	0.9500
C16—C17	1.384 (3)	C16'—C17'	1.390 (3)
C16—H16	0.9500	C16'—H16'	0.9500
C17—C18	1.383 (3)	C17'—C18'	1.392 (3)
C17—C20	1.506 (3)	C17'—C20'	1.508 (3)
C18—C19	1.387 (3)	C18'—C19'	1.386 (3)
C18—H18	0.9500	C18'—H18'	0.9500
C19—H19	0.9500	C19'—H19'	0.9500
C20—H20A	0.9800	C20'—H20D	0.9800
C20—H20B	0.9800	C20'—H20E	0.9800
C20—H20C	0.9800	C20'—H20F	0.9800

C7—N1—C6	127.70 (16)	C7'—N1'—C6'	130.64 (16)
C7—N1—H1N	113.2 (16)	C7'—N1'—H1'N	114.4 (16)
C6—N1—H1N	119.1 (16)	C6'—N1'—H1'N	113.0 (15)
C13—N2—C14	123.56 (15)	C13'—N2'—C14'	125.34 (16)
C13—N2—H2N	116.0 (13)	C13'—N2'—H2'N	116.4 (14)
C14—N2—H2N	119.7 (13)	C14'—N2'—H2'N	116.8 (14)
C2—C1—C6	120.75 (17)	C2'—C1'—C6'	120.72 (19)
C2—C1—H1	119.6	C2'—C1'—H1'	119.6
C6—C1—H1	119.6	C6'—C1'—H1'	119.6
C1—C2—C3	120.87 (18)	C3'—C2'—C1'	120.5 (2)
C1—C2—H2	119.6	C3'—C2'—H2'	119.7
C3—C2—H2	119.6	C1'—C2'—H2'	119.7
C4—C3—C2	118.63 (18)	C4'—C3'—C2'	118.95 (18)
C4—C3—H3	120.7	C4'—C3'—H3'	120.5
C2—C3—H3	120.7	C2'—C3'—H3'	120.5
C3—C4—C5	121.21 (17)	C3'—C4'—C5'	121.45 (19)
C3—C4—H4	119.4	C3'—C4'—H4'	119.3
C5—C4—H4	119.4	C5'—C4'—H4'	119.3
C4—C5—C6	120.04 (17)	C4'—C5'—C6'	119.63 (18)
C4—C5—H5	120.0	C4'—C5'—H5'	120.2
C6—C5—H5	120.0	C6'—C5'—H5'	120.2
C1—C6—N1	118.24 (16)	C5'—C6'—C1'	118.60 (17)
C1—C6—C5	118.50 (17)	C5'—C6'—N1'	124.26 (16)
N1—C6—C5	123.05 (16)	C1'—C6'—N1'	117.03 (16)
N1—C7—C8	121.94 (16)	N1'—C7'—C8'	123.72 (16)
N1—C7—C12	119.79 (16)	N1'—C7'—C12'	118.43 (16)
C8—C7—C12	118.27 (16)	C8'—C7'—C12'	117.85 (16)
C9—C8—C7	120.99 (17)	C9'—C8'—C7'	121.12 (16)
C9—C8—H8	119.5	C9'—C8'—H8'	119.4
C7—C8—H8	119.5	C7'—C8'—H8'	119.4
C8—C9—C10	121.07 (18)	C8'—C9'—C10'	121.06 (18)
C8—C9—H9	119.5	C8'—C9'—H9'	119.5
C10—C9—H9	119.5	C10'—C9'—H9'	119.5
C11—C10—C9	118.54 (18)	C11'—C10'—C9'	118.70 (18)
C11—C10—H10	120.7	C11'—C10'—H10'	120.7
C9—C10—H10	120.7	C9'—C10'—H10'	120.7
C10—C11—C12	121.60 (17)	C10'—C11'—C12'	121.66 (16)
C10—C11—H11	119.2	C10'—C11'—H11'	119.2
C12—C11—H11	119.2	C12'—C11'—H11'	119.2
C11—C12—C7	119.51 (16)	C11'—C12'—C7'	119.58 (17)
C11—C12—C13	120.31 (16)	C11'—C12'—C13'	120.30 (15)
C7—C12—C13	120.19 (16)	C7'—C12'—C13'	120.08 (16)
O1—C13—N2	122.23 (16)	O1'—C13'—N2'	122.34 (17)
O1—C13—C12	122.61 (15)	O1'—C13'—C12'	122.24 (15)
N2—C13—C12	115.15 (15)	N2'—C13'—C12'	115.41 (15)
C19—C14—C15	119.51 (17)	C15'—C14'—C19'	119.43 (17)
C19—C14—N2	120.05 (16)	C15'—C14'—N2'	122.37 (16)
C15—C14—N2	120.39 (17)	C19'—C14'—N2'	118.18 (15)
C16—C15—C14	120.12 (18)	C16'—C15'—C14'	119.47 (17)
C16—C15—H15	119.9	C16'—C15'—H15'	120.3
C14—C15—H15	119.9	C14'—C15'—H15'	120.3
C17—C16—C15	121.23 (17)	C15'—C16'—C17'	122.00 (17)
C17—C16—H16	119.4	C15'—C16'—H16'	119.0
C15—C16—H16	119.4	C17'—C16'—H16'	119.0
C18—C17—C16	117.53 (18)	C16'—C17'—C18'	117.62 (18)
C18—C17—C20	120.94 (19)	C16'—C17'—C20'	120.39 (17)
C16—C17—C20	121.53 (17)	C18'—C17'—C20'	121.99 (18)
C17—C18—C19	122.09 (19)	C19'—C18'—C17'	121.27 (18)
C17—C18—H18	119.0	C19'—C18'—H18'	119.4
C19—C18—H18	119.0	C17'—C18'—H18'	119.4
C14—C19—C18	119.51 (17)	C18'—C19'—C14'	120.18 (17)
C14—C19—H19	120.2	C18'—C19'—H19'	119.9
C18—C19—H19	120.2	C14'—C19'—H19'	119.9
C17—C20—H20A	109.5	C17'—C20'—H20D	109.5
C17—C20—H20B	109.5	C17'—C20'—H20E	109.5
H20A—C20—H20B	109.5	H20D—C20'—H20E	109.5
C17—C20—H20C	109.5	C17'—C20'—H20F	109.5
H20A—C20—H20C	109.5	H20D—C20'—H20F	109.5
H20B—C20—H20C	109.5	H20E—C20'—H20F	109.5

C6—C1—C2—C3	0.1 (3)	C6'—C1'—C2'—C3'	1.0 (3)
C1—C2—C3—C4	0.3 (3)	C1'—C2'—C3'—C4'	−2.4 (3)
C2—C3—C4—C5	−0.5 (3)	C2'—C3'—C4'—C5'	0.5 (3)
C3—C4—C5—C6	0.2 (3)	C3'—C4'—C5'—C6'	2.6 (3)
C2—C1—C6—N1	−175.43 (18)	C4'—C5'—C6'—C1'	−3.9 (3)
C2—C1—C6—C5	−0.4 (3)	C4'—C5'—C6'—N1'	−179.98 (17)
C7—N1—C6—C1	−157.58 (17)	C2'—C1'—C6'—C5'	2.2 (3)
C7—N1—C6—C5	27.7 (3)	C2'—C1'—C6'—N1'	178.51 (18)
C4—C5—C6—C1	0.2 (3)	C7'—N1'—C6'—C5'	−30.9 (3)
C4—C5—C6—N1	175.00 (18)	C7'—N1'—C6'—C1'	153.02 (18)
C6—N1—C7—C8	26.0 (3)	C6'—N1'—C7'—C8'	−2.7 (3)
C6—N1—C7—C12	−154.54 (17)	C6'—N1'—C7'—C12'	177.90 (16)
N1—C7—C8—C9	179.91 (16)	N1'—C7'—C8'—C9'	179.14 (16)
C12—C7—C8—C9	0.4 (3)	C12'—C7'—C8'—C9'	−1.5 (3)
C7—C8—C9—C10	−1.5 (3)	C7'—C8'—C9'—C10'	0.7 (3)
C8—C9—C10—C11	1.0 (3)	C8'—C9'—C10'—C11'	0.9 (3)
C9—C10—C11—C12	0.4 (3)	C9'—C10'—C11'—C12'	−1.6 (3)
C10—C11—C12—C7	−1.4 (3)	C10'—C11'—C12'—C7'	0.8 (3)
C10—C11—C12—C13	178.56 (16)	C10'—C11'—C12'—C13'	178.90 (15)
N1—C7—C12—C11	−178.50 (15)	N1'—C7'—C12'—C11'	−179.82 (15)
C8—C7—C12—C11	1.0 (2)	C8'—C7'—C12'—C11'	0.8 (2)
N1—C7—C12—C13	1.5 (2)	N1'—C7'—C12'—C13'	2.1 (2)
C8—C7—C12—C13	−179.01 (15)	C8'—C7'—C12'—C13'	−177.37 (15)
C14—N2—C13—O1	−3.9 (3)	C14'—N2'—C13'—O1'	−1.7 (3)
C14—N2—C13—C12	176.59 (16)	C14'—N2'—C13'—C12'	177.13 (15)
C11—C12—C13—O1	142.03 (18)	C11'—C12'—C13'—O1'	−144.84 (17)
C7—C12—C13—O1	−38.0 (2)	C7'—C12'—C13'—O1'	33.3 (2)
C11—C12—C13—N2	−38.5 (2)	C11'—C12'—C13'—N2'	36.4 (2)
C7—C12—C13—N2	141.49 (17)	C7'—C12'—C13'—N2'	−145.52 (16)
C13—N2—C14—C19	131.4 (2)	C13'—N2'—C14'—C15'	38.3 (3)
C13—N2—C14—C15	−51.1 (3)	C13'—N2'—C14'—C19'	−143.13 (18)
C19—C14—C15—C16	−0.3 (3)	C19'—C14'—C15'—C16'	1.7 (3)
N2—C14—C15—C16	−177.87 (17)	N2'—C14'—C15'—C16'	−179.80 (16)
C14—C15—C16—C17	0.3 (3)	C14'—C15'—C16'—C17'	−1.5 (3)
C15—C16—C17—C18	−0.1 (3)	C15'—C16'—C17'—C18'	0.3 (3)
C15—C16—C17—C20	−179.6 (2)	C15'—C16'—C17'—C20'	−178.89 (18)
C16—C17—C18—C19	−0.1 (4)	C16'—C17'—C18'—C19'	0.7 (3)
C20—C17—C18—C19	179.5 (2)	C20'—C17'—C18'—C19'	179.91 (19)
C15—C14—C19—C18	0.1 (3)	C17'—C18'—C19'—C14'	−0.5 (3)
N2—C14—C19—C18	177.73 (19)	C15'—C14'—C19'—C18'	−0.7 (3)
C17—C18—C19—C14	0.0 (4)	N2'—C14'—C19'—C18'	−179.27 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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′···Cg6^iv	0.95	2.97	3.933 (2)	175

Symmetry codes: (i) −x+1/2, y−1/2, z−1/2; (ii) x, y, z−1; (iii) x, y, z+1; (iv) x+1/2, −y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈N₂O
M_r	302.36
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	93
a, b, c (Å)	26.537 (3), 17.7337 (19), 6.8457 (7)
V (Å³)	3221.6 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.40 × 0.33

Data collection
Diffractometer	Rigaku SPIDER diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	21180, 3989, 3913
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.074, 1.01
No. of reflections	3989
No. of parameters	433
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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'···Cg6^iv	0.95	2.97	3.933 (2)	175

Symmetry codes: (i) −x+1/2, y−1/2, z−1/2; (ii) x, y, z−1; (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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