3-Anilino-N-p-tolyl-benzamide.

The title compound, C(20)H(18)N(2)O, which crystallizes with two independent mol-ecules (A and B) in the asymmetric unit, is composed of three aromatic rings (I, II and III). The conformation of the two independent mol-ecules 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 mol-ecule A, and 29.60 (9) and 70.72 (9)°, respectively, for mol-ecule B. Rings I and III are inclined to one another by 86.57 (9)° in mol-ecule A, and 64.59 (10)° in mol-ecule B. The mol-ecular structures are stabilized by intra-molecular N-H⋯O hydrogen bonds. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains propagating in the [010] direction. In addition, a number of C-H⋯π inter-actions 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 = 302.36

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 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

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H18N2O	Dx = 1.247 Mg m−3
Mr = 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

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

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(Fo2) + (0.0338P)2 + 0.690P] where P = (Fo2 + 2Fc2)/3
3989 reflections	(Δ/σ)max = 0.001
433 parameters	Δρmax = 0.20 e Å−3
1 restraint	Δρmin = −0.14 e Å−3

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
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)*

	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)

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)

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'···Cg6iv	0.95	2.97	3.933 (2)	175

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′⋯Cg6iv	0.95	2.97	3.933 (2)	175

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . 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′)