(E)-1-(3,4-Dimethyl-benzyl-idene)-2,2-diphenyl-hydrazine.

The asymmetric unit of the title compound, C(21)H(20)N(2), contain two mol-ecules, both of them showing an E configuration of the C=N bond. The dihedral angles between the phenyl rings in the phenyl-hydrazone groups are 86.84 (10) and 84.85 (8)° for the two mol-ecules. Inter-molecular C-H⋯π inter-actions are observed in the crystal structure.

Related literature

For applications of hydrazones, see: Angell et al. (2006 ▶); Buss et al. (2004 ▶); Melnyk et al. (2006 ▶); Ranford et al. (1998 ▶). For related structures see: Clulow et al. (2008 ▶); Mendoza et al. (2010 ▶).

Experimental

Crystal data

C21H20N2

M = 300.39

Triclinic,

a = 9.9375 (5) Å

b = 10.6322 (5) Å

c = 17.5680 (8) Å

α = 77.530 (4)°

β = 76.480 (4)°

γ = 77.074 (4)°

V = 1732.60 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.61 × 0.42 × 0.27 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini diffractometer

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.971, T max = 0.984

12246 measured reflections

6288 independent reflections

3202 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.100

S = 0.85

6288 reflections

420 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.11 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis n class="Disease">RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811015352/bt5512sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015352/bt5512Isup2.hkl

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

C21H20N2	Z = 4
Mr = 300.39	F(000) = 640
Triclinic, P1	Dx = 1.152 Mg m−3
a = 9.9375 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.6322 (5) Å	Cell parameters from 3720 reflections
c = 17.5680 (8) Å	θ = 3.4–25.2°
α = 77.530 (4)°	µ = 0.07 mm−1
β = 76.480 (4)°	T = 293 K
γ = 77.074 (4)°	Prism, colorless
V = 1732.60 (14) Å3	0.61 × 0.42 × 0.27 mm

Oxford Diffraction Xcalibur Atlas Gemini diffractometer	6288 independent reflections
graphite	3202 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm-1	Rint = 0.027
ω scans	θmax = 25.3°, θmin = 3.4°
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	h = −9→11
Tmin = 0.971, Tmax = 0.984	k = −10→12
12246 measured reflections	l = −21→20

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0496P)2] where P = (Fo2 + 2Fc2)/3
S = 0.85	(Δ/σ)max = 0.001
6288 reflections	Δρmax = 0.15 e Å−3
420 parameters	Δρmin = −0.11 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0220 (12)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
N1	0.36159 (15)	0.39399 (14)	0.36518 (8)	0.0660 (4)
N2	0.41791 (15)	0.32889 (15)	0.43054 (8)	0.0756 (4)
C16	0.32092 (19)	0.29285 (16)	0.49984 (10)	0.0597 (4)
C21	0.1779 (2)	0.33547 (18)	0.50422 (11)	0.0730 (5)
H21	0.1443	0.3888	0.4607	0.088*
C20	0.0850 (2)	0.2992 (2)	0.57287 (12)	0.0858 (6)
H20	−0.0111	0.3292	0.5752	0.103*
C19	0.1307 (3)	0.2199 (2)	0.63774 (12)	0.0875 (6)
H19	0.0669	0.1956	0.6837	0.105*
C18	0.2719 (3)	0.17699 (19)	0.63365 (11)	0.0812 (6)
H18	0.3043	0.1226	0.6772	0.097*
C17	0.3673 (2)	0.21310 (18)	0.56583 (10)	0.0730 (5)
H17	0.4632	0.1838	0.5643	0.088*
C10	0.56693 (18)	0.29103 (18)	0.42665 (9)	0.0601 (5)
C11	0.6403 (2)	0.37197 (19)	0.44503 (11)	0.0787 (6)
H11	0.5936	0.4524	0.4589	0.094*
C12	0.7826 (3)	0.3344 (3)	0.44297 (12)	0.0907 (6)
H12	0.8317	0.3887	0.4563	0.109*
C13	0.8510 (2)	0.2186 (3)	0.42167 (12)	0.0936 (7)
H13	0.9472	0.1932	0.4204	0.112*
C14	0.7801 (3)	0.1397 (2)	0.40227 (13)	0.0963 (7)
H14	0.8281	0.0604	0.3873	0.116*
C15	0.6372 (2)	0.1753 (2)	0.40443 (11)	0.0806 (6)
H15	0.5891	0.1204	0.3908	0.097*
C1	0.44210 (18)	0.43109 (16)	0.29977 (10)	0.0617 (5)
H1	0.5391	0.4145	0.2964	0.074*
C2	0.38244 (17)	0.49919 (15)	0.23059 (9)	0.0532 (4)
C7	0.23891 (17)	0.52161 (16)	0.23122 (10)	0.0606 (5)
H7	0.1774	0.4926	0.2771	0.073*
C6	0.18753 (17)	0.58661 (16)	0.16420 (10)	0.0617 (5)
H6	0.0913	0.5999	0.1656	0.074*
C5	0.27467 (16)	0.63270 (15)	0.09501 (9)	0.0513 (4)
C4	0.41897 (16)	0.61329 (15)	0.09341 (9)	0.0518 (4)
C3	0.46939 (16)	0.54615 (16)	0.16103 (10)	0.0572 (4)
H3	0.5657	0.532	0.1597	0.069*
C8	0.51750 (17)	0.66410 (19)	0.01989 (10)	0.0770 (5)
H8A	0.613	0.6321	0.0267	0.115*
H8B	0.4992	0.7581	0.0111	0.115*
H8C	0.5032	0.6345	−0.025	0.115*
C9	0.21465 (17)	0.70064 (17)	0.02243 (10)	0.0686 (5)
H9A	0.1143	0.7069	0.0346	0.103*
H9B	0.2544	0.6513	−0.0199	0.103*
H9C	0.2371	0.7869	0.0063	0.103*
N3	0.19466 (12)	0.19292 (13)	0.00863 (7)	0.0525 (3)
N4	0.19869 (13)	0.19943 (13)	−0.07059 (7)	0.0565 (4)
C31	0.18030 (15)	0.32507 (16)	−0.11695 (9)	0.0477 (4)
C32	0.13244 (15)	0.43680 (16)	−0.08245 (9)	0.0522 (4)
H32	0.1149	0.4297	−0.0275	0.063*
C33	0.11102 (16)	0.55796 (17)	−0.12972 (10)	0.0599 (4)
H33	0.0781	0.6322	−0.106	0.072*
C34	0.13712 (17)	0.57179 (18)	−0.21115 (11)	0.0657 (5)
H34	0.1215	0.6542	−0.2424	0.079*
C35	0.18661 (18)	0.46180 (19)	−0.24540 (10)	0.0663 (5)
H35	0.2056	0.4698	−0.3005	0.08*
C36	0.20849 (17)	0.33961 (17)	−0.19914 (9)	0.0600 (4)
H36	0.2426	0.266	−0.2233	0.072*
C37	0.23353 (16)	0.08491 (15)	−0.10724 (8)	0.0492 (4)
C38	0.12895 (17)	0.03792 (17)	−0.12529 (10)	0.0587 (4)
H38	0.0355	0.078	−0.1116	0.07*
C39	0.1620 (2)	−0.06805 (18)	−0.16345 (10)	0.0681 (5)
H39	0.091	−0.0988	−0.1763	0.082*
C40	0.2989 (2)	−0.12838 (17)	−0.18261 (10)	0.0704 (5)
H40	0.3213	−0.2002	−0.2084	0.084*
C41	0.4032 (2)	−0.08287 (19)	−0.16375 (10)	0.0749 (5)
H41	0.4963	−0.1245	−0.1763	0.09*
C42	0.37124 (17)	0.02402 (18)	−0.12631 (10)	0.0648 (5)
H42	0.4425	0.055	−0.1139	0.078*
C22	0.21859 (15)	0.08199 (17)	0.05388 (9)	0.0532 (4)
H22	0.2346	0.0053	0.0333	0.064*
C23	0.22101 (14)	0.07456 (16)	0.13727 (9)	0.0479 (4)
C28	0.24973 (16)	−0.04682 (16)	0.18511 (9)	0.0544 (4)
H28	0.2625	−0.1219	0.1633	0.065*
C27	0.26025 (16)	−0.06090 (16)	0.26412 (9)	0.0572 (4)
C26	0.23930 (16)	0.05158 (17)	0.29740 (9)	0.0575 (4)
C25	0.20856 (17)	0.17242 (17)	0.25014 (10)	0.0628 (5)
H25	0.1929	0.2477	0.2722	0.075*
C24	0.20038 (16)	0.18513 (16)	0.17172 (10)	0.0591 (5)
H24	0.181	0.2681	0.1416	0.071*
C29	0.2983 (2)	−0.19570 (18)	0.31134 (11)	0.0935 (7)
H29A	0.393	−0.2085	0.3194	0.14*
H29B	0.2911	−0.2606	0.2827	0.14*
H29C	0.235	−0.2038	0.3619	0.14*
C30	0.2536 (2)	0.0441 (2)	0.38198 (10)	0.0887 (6)
H30A	0.2308	0.1307	0.3948	0.133*
H30B	0.3486	0.0058	0.3876	0.133*
H30C	0.1904	−0.0089	0.4173	0.133*

	U11	U22	U33	U12	U13	U23
N1	0.0642 (9)	0.0726 (10)	0.0561 (9)	−0.0088 (7)	−0.0201 (8)	0.0053 (8)
N2	0.0601 (10)	0.0977 (12)	0.0557 (9)	−0.0060 (8)	−0.0172 (8)	0.0129 (8)
C16	0.0683 (12)	0.0599 (12)	0.0512 (11)	−0.0110 (9)	−0.0159 (10)	−0.0064 (9)
C21	0.0701 (13)	0.0872 (15)	0.0601 (12)	−0.0164 (10)	−0.0175 (10)	−0.0020 (10)
C20	0.0763 (13)	0.1129 (18)	0.0689 (14)	−0.0269 (12)	−0.0096 (12)	−0.0118 (13)
C19	0.1008 (18)	0.1049 (18)	0.0549 (13)	−0.0310 (13)	−0.0027 (12)	−0.0107 (12)
C18	0.1102 (18)	0.0804 (15)	0.0494 (12)	−0.0108 (13)	−0.0185 (12)	−0.0072 (10)
C17	0.0839 (13)	0.0763 (14)	0.0545 (12)	−0.0046 (10)	−0.0190 (11)	−0.0067 (10)
C10	0.0620 (12)	0.0657 (13)	0.0489 (10)	−0.0040 (10)	−0.0170 (9)	−0.0029 (9)
C11	0.0801 (15)	0.0813 (15)	0.0751 (13)	−0.0075 (12)	−0.0145 (11)	−0.0223 (11)
C12	0.0837 (17)	0.115 (2)	0.0818 (15)	−0.0300 (14)	−0.0284 (12)	−0.0101 (14)
C13	0.0675 (14)	0.121 (2)	0.0756 (15)	−0.0010 (15)	−0.0203 (11)	0.0084 (14)
C14	0.0977 (19)	0.0835 (17)	0.0968 (17)	0.0175 (14)	−0.0238 (14)	−0.0222 (13)
C15	0.0903 (16)	0.0723 (15)	0.0818 (14)	−0.0036 (12)	−0.0299 (12)	−0.0158 (11)
C1	0.0564 (11)	0.0663 (12)	0.0590 (11)	−0.0090 (9)	−0.0171 (9)	0.0007 (9)
C2	0.0523 (10)	0.0510 (11)	0.0562 (10)	−0.0111 (8)	−0.0165 (9)	−0.0005 (8)
C7	0.0534 (11)	0.0666 (12)	0.0596 (11)	−0.0198 (8)	−0.0100 (9)	0.0021 (9)
C6	0.0472 (10)	0.0696 (12)	0.0693 (12)	−0.0165 (8)	−0.0196 (9)	0.0009 (10)
C5	0.0527 (10)	0.0492 (10)	0.0564 (10)	−0.0152 (8)	−0.0194 (9)	−0.0025 (8)
C4	0.0519 (10)	0.0519 (11)	0.0541 (10)	−0.0164 (8)	−0.0148 (8)	−0.0020 (8)
C3	0.0451 (9)	0.0667 (12)	0.0603 (11)	−0.0117 (8)	−0.0192 (9)	−0.0011 (9)
C8	0.0620 (12)	0.1005 (15)	0.0667 (12)	−0.0268 (10)	−0.0176 (10)	0.0070 (11)
C9	0.0655 (11)	0.0738 (13)	0.0696 (12)	−0.0174 (9)	−0.0294 (9)	0.0034 (9)
N3	0.0526 (8)	0.0588 (10)	0.0472 (8)	−0.0148 (6)	−0.0124 (6)	−0.0035 (7)
N4	0.0715 (9)	0.0548 (10)	0.0448 (8)	−0.0116 (7)	−0.0162 (7)	−0.0065 (7)
C31	0.0430 (9)	0.0545 (11)	0.0468 (10)	−0.0125 (7)	−0.0134 (7)	−0.0023 (8)
C32	0.0488 (10)	0.0586 (12)	0.0495 (10)	−0.0082 (8)	−0.0143 (8)	−0.0066 (9)
C33	0.0588 (11)	0.0573 (12)	0.0652 (12)	−0.0074 (8)	−0.0224 (9)	−0.0065 (9)
C34	0.0697 (12)	0.0599 (13)	0.0661 (13)	−0.0175 (9)	−0.0227 (10)	0.0079 (10)
C35	0.0762 (13)	0.0729 (14)	0.0484 (10)	−0.0223 (10)	−0.0131 (9)	0.0024 (10)
C36	0.0689 (11)	0.0618 (12)	0.0499 (11)	−0.0145 (9)	−0.0128 (9)	−0.0071 (9)
C37	0.0480 (10)	0.0512 (10)	0.0454 (9)	−0.0084 (8)	−0.0091 (8)	−0.0029 (8)
C38	0.0478 (10)	0.0633 (12)	0.0664 (11)	−0.0100 (8)	−0.0120 (8)	−0.0128 (9)
C39	0.0707 (13)	0.0675 (13)	0.0717 (12)	−0.0191 (10)	−0.0167 (10)	−0.0142 (10)
C40	0.0905 (15)	0.0592 (13)	0.0564 (11)	−0.0060 (11)	−0.0071 (11)	−0.0150 (9)
C41	0.0582 (12)	0.0847 (15)	0.0670 (13)	0.0043 (10)	0.0001 (10)	−0.0133 (11)
C42	0.0472 (11)	0.0827 (14)	0.0636 (12)	−0.0117 (9)	−0.0085 (9)	−0.0132 (10)
C22	0.0523 (10)	0.0564 (12)	0.0525 (10)	−0.0151 (8)	−0.0115 (8)	−0.0063 (9)
C23	0.0423 (9)	0.0534 (11)	0.0471 (10)	−0.0100 (7)	−0.0103 (7)	−0.0034 (8)
C28	0.0608 (10)	0.0501 (11)	0.0550 (11)	−0.0140 (8)	−0.0135 (8)	−0.0085 (8)
C27	0.0596 (11)	0.0573 (12)	0.0528 (11)	−0.0108 (8)	−0.0156 (8)	−0.0004 (9)
C26	0.0565 (10)	0.0632 (12)	0.0516 (10)	−0.0047 (8)	−0.0154 (8)	−0.0081 (9)
C25	0.0686 (12)	0.0593 (12)	0.0596 (12)	0.0005 (9)	−0.0171 (9)	−0.0163 (9)
C24	0.0625 (11)	0.0524 (11)	0.0598 (11)	−0.0024 (8)	−0.0192 (9)	−0.0048 (9)
C29	0.1421 (19)	0.0656 (14)	0.0724 (13)	−0.0160 (12)	−0.0396 (13)	0.0063 (11)
C30	0.1113 (16)	0.0927 (16)	0.0646 (12)	−0.0006 (12)	−0.0351 (12)	−0.0180 (11)

N1—C1	1.2773 (19)	N3—C22	1.2797 (18)
N1—N2	1.3765 (17)	N3—N4	1.3701 (16)
N2—C16	1.405 (2)	N4—C31	1.4041 (19)
N2—C10	1.434 (2)	N4—C37	1.4362 (18)
C16—C21	1.381 (2)	C31—C36	1.386 (2)
C16—C17	1.388 (2)	C31—C32	1.389 (2)
C21—C20	1.376 (2)	C32—C33	1.376 (2)
C21—H21	0.93	C32—H32	0.93
C20—C19	1.369 (3)	C33—C34	1.374 (2)
C20—H20	0.93	C33—H33	0.93
C19—C18	1.364 (3)	C34—C35	1.371 (2)
C19—H19	0.93	C34—H34	0.93
C18—C17	1.379 (2)	C35—C36	1.377 (2)
C18—H18	0.93	C35—H35	0.93
C17—H17	0.93	C36—H36	0.93
C10—C15	1.360 (2)	C37—C38	1.373 (2)
C10—C11	1.374 (2)	C37—C42	1.374 (2)
C11—C12	1.374 (3)	C38—C39	1.373 (2)
C11—H11	0.93	C38—H38	0.93
C12—C13	1.350 (3)	C39—C40	1.366 (2)
C12—H12	0.93	C39—H39	0.93
C13—C14	1.347 (3)	C40—C41	1.368 (2)
C13—H13	0.93	C40—H40	0.93
C14—C15	1.379 (3)	C41—C42	1.374 (2)
C14—H14	0.93	C41—H41	0.93
C15—H15	0.93	C42—H42	0.93
C1—C2	1.455 (2)	C22—C23	1.455 (2)
C1—H1	0.93	C22—H22	0.93
C2—C3	1.387 (2)	C23—C24	1.390 (2)
C2—C7	1.390 (2)	C23—C28	1.390 (2)
C7—C6	1.377 (2)	C28—C27	1.390 (2)
C7—H7	0.93	C28—H28	0.93
C6—C5	1.381 (2)	C27—C26	1.396 (2)
C6—H6	0.93	C27—C29	1.509 (2)
C5—C4	1.397 (2)	C26—C25	1.384 (2)
C5—C9	1.506 (2)	C26—C30	1.509 (2)
C4—C3	1.387 (2)	C25—C24	1.375 (2)
C4—C8	1.504 (2)	C25—H25	0.93
C3—H3	0.93	C24—H24	0.93
C8—H8A	0.96	C29—H29A	0.96
C8—H8B	0.96	C29—H29B	0.96
C8—H8C	0.96	C29—H29C	0.96
C9—H9A	0.96	C30—H30A	0.96
C9—H9B	0.96	C30—H30B	0.96
C9—H9C	0.96	C30—H30C	0.96
C1—N1—N2	120.22 (14)	C22—N3—N4	120.47 (13)
N1—N2—C16	116.03 (14)	N3—N4—C31	116.75 (12)
N1—N2—C10	122.07 (14)	N3—N4—C37	122.52 (13)
C16—N2—C10	121.73 (13)	C31—N4—C37	120.46 (12)
C21—C16—C17	118.38 (17)	C36—C31—C32	118.44 (15)
C21—C16—N2	121.21 (15)	C36—C31—N4	120.01 (15)
C17—C16—N2	120.41 (16)	C32—C31—N4	121.54 (14)
C20—C21—C16	120.14 (18)	C33—C32—C31	119.90 (15)
C20—C21—H21	119.9	C33—C32—H32	120
C16—C21—H21	119.9	C31—C32—H32	120
C19—C20—C21	121.4 (2)	C34—C33—C32	121.46 (16)
C19—C20—H20	119.3	C34—C33—H33	119.3
C21—C20—H20	119.3	C32—C33—H33	119.3
C18—C19—C20	118.7 (2)	C35—C34—C33	118.75 (16)
C18—C19—H19	120.7	C35—C34—H34	120.6
C20—C19—H19	120.7	C33—C34—H34	120.6
C19—C18—C17	120.99 (18)	C34—C35—C36	120.70 (16)
C19—C18—H18	119.5	C34—C35—H35	119.7
C17—C18—H18	119.5	C36—C35—H35	119.7
C18—C17—C16	120.36 (18)	C35—C36—C31	120.73 (16)
C18—C17—H17	119.8	C35—C36—H36	119.6
C16—C17—H17	119.8	C31—C36—H36	119.6
C15—C10—C11	119.31 (17)	C38—C37—C42	119.71 (15)
C15—C10—N2	120.53 (17)	C38—C37—N4	119.82 (13)
C11—C10—N2	120.16 (17)	C42—C37—N4	120.44 (14)
C10—C11—C12	120.12 (18)	C39—C38—C37	120.19 (15)
C10—C11—H11	119.9	C39—C38—H38	119.9
C12—C11—H11	119.9	C37—C38—H38	119.9
C13—C12—C11	120.0 (2)	C40—C39—C38	120.10 (17)
C13—C12—H12	120	C40—C39—H39	120
C11—C12—H12	120	C38—C39—H39	120
C14—C13—C12	120.2 (2)	C39—C40—C41	119.84 (17)
C14—C13—H13	119.9	C39—C40—H40	120.1
C12—C13—H13	119.9	C41—C40—H40	120.1
C13—C14—C15	120.7 (2)	C40—C41—C42	120.45 (16)
C13—C14—H14	119.7	C40—C41—H41	119.8
C15—C14—H14	119.7	C42—C41—H41	119.8
C10—C15—C14	119.66 (19)	C37—C42—C41	119.70 (16)
C10—C15—H15	120.2	C37—C42—H42	120.1
C14—C15—H15	120.2	C41—C42—H42	120.1
N1—C1—C2	120.15 (16)	N3—C22—C23	120.75 (15)
N1—C1—H1	119.9	N3—C22—H22	119.6
C2—C1—H1	119.9	C23—C22—H22	119.6
C3—C2—C7	117.54 (14)	C24—C23—C28	117.36 (14)
C3—C2—C1	120.02 (15)	C24—C23—C22	122.72 (15)
C7—C2—C1	122.44 (15)	C28—C23—C22	119.89 (15)
C6—C7—C2	120.26 (15)	C27—C28—C23	122.90 (15)
C6—C7—H7	119.9	C27—C28—H28	118.6
C2—C7—H7	119.9	C23—C28—H28	118.6
C7—C6—C5	121.94 (15)	C28—C27—C26	118.71 (15)
C7—C6—H6	119	C28—C27—C29	119.93 (15)
C5—C6—H6	119	C26—C27—C29	121.33 (15)
C6—C5—C4	118.81 (14)	C25—C26—C27	118.42 (14)
C6—C5—C9	120.28 (14)	C25—C26—C30	119.86 (16)
C4—C5—C9	120.90 (14)	C27—C26—C30	121.70 (16)
C3—C4—C5	118.58 (15)	C24—C25—C26	122.32 (16)
C3—C4—C8	120.75 (15)	C24—C25—H25	118.8
C5—C4—C8	120.67 (14)	C26—C25—H25	118.8
C4—C3—C2	122.85 (15)	C25—C24—C23	120.28 (15)
C4—C3—H3	118.6	C25—C24—H24	119.9
C2—C3—H3	118.6	C23—C24—H24	119.9
C4—C8—H8A	109.5	C27—C29—H29A	109.5
C4—C8—H8B	109.5	C27—C29—H29B	109.5
H8A—C8—H8B	109.5	H29A—C29—H29B	109.5
C4—C8—H8C	109.5	C27—C29—H29C	109.5
H8A—C8—H8C	109.5	H29A—C29—H29C	109.5
H8B—C8—H8C	109.5	H29B—C29—H29C	109.5
C5—C9—H9A	109.5	C26—C30—H30A	109.5
C5—C9—H9B	109.5	C26—C30—H30B	109.5
H9A—C9—H9B	109.5	H30A—C30—H30B	109.5
C5—C9—H9C	109.5	C26—C30—H30C	109.5
H9A—C9—H9C	109.5	H30A—C30—H30C	109.5
H9B—C9—H9C	109.5	H30B—C30—H30C	109.5
C1—N1—N2—C16	179.59 (15)	C22—N3—N4—C31	−175.97 (13)
C1—N1—N2—C10	−5.1 (2)	C22—N3—N4—C37	−1.9 (2)
N1—N2—C16—C21	−8.0 (2)	N3—N4—C31—C36	168.14 (13)
C10—N2—C16—C21	176.64 (17)	C37—N4—C31—C36	−6.0 (2)
N1—N2—C16—C17	172.04 (15)	N3—N4—C31—C32	−12.63 (19)
C10—N2—C16—C17	−3.3 (3)	C37—N4—C31—C32	173.21 (13)
C17—C16—C21—C20	0.2 (3)	C36—C31—C32—C33	1.5 (2)
N2—C16—C21—C20	−179.79 (16)	N4—C31—C32—C33	−177.73 (13)
C16—C21—C20—C19	−0.6 (3)	C31—C32—C33—C34	−0.6 (2)
C21—C20—C19—C18	0.3 (3)	C32—C33—C34—C35	−0.5 (2)
C20—C19—C18—C17	0.4 (3)	C33—C34—C35—C36	0.6 (2)
C19—C18—C17—C16	−0.8 (3)	C34—C35—C36—C31	0.3 (2)
C21—C16—C17—C18	0.5 (3)	C32—C31—C36—C35	−1.4 (2)
N2—C16—C17—C18	−179.52 (15)	N4—C31—C36—C35	177.86 (14)
N1—N2—C10—C15	−86.5 (2)	N3—N4—C37—C38	103.54 (17)
C16—N2—C10—C15	88.6 (2)	C31—N4—C37—C38	−82.65 (18)
N1—N2—C10—C11	93.2 (2)	N3—N4—C37—C42	−78.19 (18)
C16—N2—C10—C11	−91.7 (2)	C31—N4—C37—C42	95.62 (18)
C15—C10—C11—C12	−1.7 (3)	C42—C37—C38—C39	−1.1 (2)
N2—C10—C11—C12	178.59 (16)	N4—C37—C38—C39	177.16 (15)
C10—C11—C12—C13	1.0 (3)	C37—C38—C39—C40	0.9 (3)
C11—C12—C13—C14	0.1 (3)	C38—C39—C40—C41	−0.1 (3)
C12—C13—C14—C15	−0.5 (3)	C39—C40—C41—C42	−0.6 (3)
C11—C10—C15—C14	1.3 (3)	C38—C37—C42—C41	0.4 (2)
N2—C10—C15—C14	−178.98 (17)	N4—C37—C42—C41	−177.84 (15)
C13—C14—C15—C10	−0.2 (3)	C40—C41—C42—C37	0.5 (3)
N2—N1—C1—C2	179.62 (14)	N4—N3—C22—C23	177.09 (12)
N1—C1—C2—C3	176.21 (15)	N3—C22—C23—C24	−1.1 (2)
N1—C1—C2—C7	−2.8 (2)	N3—C22—C23—C28	−178.83 (13)
C3—C2—C7—C6	0.9 (2)	C24—C23—C28—C27	−0.9 (2)
C1—C2—C7—C6	179.98 (15)	C22—C23—C28—C27	176.88 (14)
C2—C7—C6—C5	−0.7 (2)	C23—C28—C27—C26	0.9 (2)
C7—C6—C5—C4	−0.4 (2)	C23—C28—C27—C29	−177.19 (15)
C7—C6—C5—C9	178.62 (14)	C28—C27—C26—C25	0.2 (2)
C6—C5—C4—C3	1.2 (2)	C29—C27—C26—C25	178.17 (16)
C9—C5—C4—C3	−177.80 (14)	C28—C27—C26—C30	−178.03 (16)
C6—C5—C4—C8	−178.79 (15)	C29—C27—C26—C30	0.0 (2)
C9—C5—C4—C8	2.2 (2)	C27—C26—C25—C24	−1.1 (2)
C5—C4—C3—C2	−1.0 (2)	C30—C26—C25—C24	177.13 (16)
C8—C4—C3—C2	179.01 (15)	C26—C25—C24—C23	1.0 (2)
C7—C2—C3—C4	−0.1 (2)	C28—C23—C24—C25	0.0 (2)
C1—C2—C3—C4	−179.15 (14)	C22—C23—C24—C25	−177.75 (14)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C31–C36, C37–C42, C2–C7 and C23–C28 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg1i	0.93	2.81	3.7152 (18)	166
C6—H6···Cg1ii	0.93	2.66	3.5506 (19)	160
C9—H9C···Cg2iii	0.96	2.97	3.7170 (19)	136
C29—H29B···Cg3iv	0.96	3.00	3.931 (2)	165
C41—H41···Cg4i	0.93	2.83	3.590 (2)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C31–C36, C37–C42, C2–C7 and C23–C28 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg1i	0.93	2.81	3.7152 (18)	166
C6—H6⋯Cg1ii	0.93	2.66	3.5506 (19)	160
C9—H9C⋯Cg2iii	0.96	2.97	3.7170 (19)	136
C29—H29B⋯Cg3iv	0.96	3.00	3.931 (2)	165
C41—H41⋯Cg4i	0.93	2.83	3.590 (2)	139

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