1,2-Bis(2-tert-butyl­phenyl­imino)-1,2-dihydro­acenaphthyl­ene

The crystal structure of the title compound, C₃₂H₃₂N₂, reveals a dimeric association of α-diimine units into centrosymmetric dimers via inter­molecular non-classical C—H...N hydrogen bonds. There is also intra­molecular non-classical C—H...N bonding between the methyl groups and the N atoms of the α-diimine unit. In addition, the crystal packing indicates π–π inter­actions between acenaphthyl­ene rings [3.888 (7) Å]. The deviation from a planar arrangement of the mol­ecule can be attributed to both inter- and intra­molecular non-classical hydrogen bonding.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.044
• wR factor = 0.079
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         44 Perc.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C5     -   C6      ..       5.98 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C8     -   C9      ..       6.08 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C14    -   C15     ..       6.56 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C25    -   C28     ..       5.60 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C25
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C26
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.11 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The present report describes the main structural features of a novel α-diimine, as given in Scheme 1 and Figure 1. This molecule is bis(N-2-tert-butylphenyl)imineacenaphthene, in which the two tert-butyl substituents on the aromatic rings are cis to each other.

In addition, another strong feature of this molecular structure is the presence of molecular interactions via non-classical hydrogen bonds (Jeffrey et al., 1985), represented as C—H···N. Each α-diimine unit presents two intermolecular interactions, generating a dimeric structure with an inversion center, as shown in Figure 2. The geometric parameters of all non-classical interactions are listed in Table 1.

The dimers are related by translation along the crystallographic axis a. The cell packing shows that the dimers present π-π interactions between the acenaphthenequine rings [C4=C9···C9ⁱⁱ=C4ⁱⁱ=3.880 (7) Å; symmetry code: (ii) 1 - x, 1 - y, 1 - z] (Fig. 3), in agreement with results found in the literature (Aoki & Salam, 2001).

Lastly, it is believed that both the inter- as well as the intramolecular interactions are partly responsible for the large deviation of planarity shown between the aromatic rings and the tert-butyl substituents, C13—C14—C15—C16—C17—C18 (r.m.s. = 0.0118) and C19—C20—C21—C22—C23—C24 (r.m.s. = 0.0030), of 28.84 (7)°. In addition, the torsion angles formed by the atoms C5—C1—N1—C13, of -7.7 (4)°, and C3—C2—N2—C19, of 10.8 (4)°, are also ascribed to the aforementioned deviation.

Related literature

For related literature, see: Aoki & Salam (2001); Jeffrey et al. (1985).

S2. Experimental

0.5465 g (3 mmole) of acenaphthenequinone was placed in a 100 ml round bottom flask, as well as 0.935 ml (6 mmole) of 2-tert-butylaniline, with MeOH (30 ml) as the solvent and glacial acetic acid as catalyst (5 drops). The flask was connected to a Liebig condenser and the reaction mixture was kept under reflux for 3 h, after which heating was stopped. After cooling to room temperature, a red solid precipitated. The mixture was filtered and the solid washed with MeOH (20 ml). The red precipitate was recrystallized from MeOH, giving small red crystals suitable for X ray crystallography. (Yield: 85%, Melting point: 485 K)

S3. Refinement

The hydrogen atoms of phenyl rings and acenaphthene ring were fixed geometrically to a distance 0.93 Å; the carbon rings and its respective atoms have been dealt with U_iso(H) 1.2 U_eq (Csp²). The hydrogen atom H23 was located in the Fourier map and refined. The hydrogen atoms of methyl group were fixed geometrically to a distance 0.96 Å; the carbon methyl and its respective atoms have been dealt with U_iso(H) 1.5 U_eq (Csp³).

Computing details

Data collection: COSMO (Bruker, 2004) and APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. ORTEP drawing of bis(N-2-tert-butylphenyl)imineacenaphthene. Thermal ellipsoids with 50% probability. Hydrogen atoms were omitted so as not to encumber the drawing.
	Fig. 2. Representation of all non-classical inter- and intramolecular interactions in the dimer.[symmetry code: (i) -x, 1 - y, 1 - z].
	Fig. 3. Representation of the packing along of crystallographic axis a. [symmetry code: (ii) 1 - x, 1 - y, 1 - z].

1,2-Bis(2-tert-butylphenylimino)-1,2-dihydroacenaphthylene

Crystal data

C32H32N2	Z = 2
Mr = 444.60	F(000) = 476
Triclinic, P1	Dx = 1.163 Mg m^−3
Hall symbol: -P 1	Melting point: 485 K
a = 10.0996 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.3843 (7) Å	θ = 1–30°
c = 12.4174 (7) Å	µ = 0.07 mm^−1
α = 60.771 (3)°	T = 291 K
β = 73.256 (4)°	Block, red
γ = 71.768 (3)°	0.54 × 0.10 × 0.08 mm
V = 1270.06 (13) Å^3

Data collection

Bruker APEX II CCD area-detector diffractometer	2066 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.068
Graphite monochromator	θmax = 25.5°, θmin = 3.1°
φ and ω scans	h = −12→12
21526 measured reflections	k = −14→14
4709 independent reflections	l = −15→15

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.079	w = 1/[σ^2(Fo^2) + (0.02P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
4709 reflections	Δρmax = 0.15 e Å^−3
312 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0177 (11)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.3511 (2)	0.59137 (18)	0.23428 (16)	0.0499 (5)
C2	0.3089 (2)	0.47043 (17)	0.34154 (16)	0.0499 (5)
C3	0.4264 (2)	0.40396 (19)	0.41384 (18)	0.0539 (5)
C4	0.5341 (2)	0.47330 (19)	0.34771 (19)	0.0537 (5)
C5	0.4974 (2)	0.58409 (18)	0.24060 (18)	0.0518 (5)
C6	0.5966 (2)	0.65484 (19)	0.16418 (19)	0.0682 (6)
H6	0.5753	0.7279	0.0920	0.082*
C7	0.7324 (3)	0.6146 (3)	0.1972 (3)	0.0865 (8)
H7	0.8006	0.6623	0.1454	0.104*
C8	0.7667 (3)	0.5086 (3)	0.3021 (3)	0.0865 (8)
H8	0.8572	0.4856	0.3207	0.104*
C9	0.6671 (3)	0.4327 (2)	0.3833 (2)	0.0707 (6)
C10	0.6881 (3)	0.3190 (3)	0.4922 (3)	0.0854 (8)
H10	0.7746	0.2886	0.5200	0.102*
C11	0.5831 (3)	0.2532 (2)	0.5570 (2)	0.0856 (7)
H11	0.5992	0.1791	0.6296	0.103*
C12	0.4509 (2)	0.29298 (19)	0.51840 (18)	0.0705 (6)
H12	0.3819	0.2448	0.5631	0.085*
C13	0.28881 (17)	0.78949 (17)	0.06525 (17)	0.0485 (5)
C14	0.27507 (17)	0.82530 (17)	−0.05757 (16)	0.0475 (5)
C15	0.29109 (19)	0.94722 (18)	−0.14324 (17)	0.0630 (6)
H15	0.2858	0.9738	−0.2263	0.076*
C16	0.3145 (2)	1.03100 (18)	−0.11115 (19)	0.0749 (6)
H16	0.3251	1.1118	−0.1720	0.090*
C17	0.3221 (2)	0.99505 (19)	0.0098 (2)	0.0726 (6)
H17	0.3353	1.0518	0.0325	0.087*
C18	0.31013 (19)	0.87446 (19)	0.09798 (17)	0.0644 (6)
H18	0.3163	0.8494	0.1805	0.077*
C19	0.14738 (18)	0.33474 (17)	0.44951 (17)	0.0498 (5)
C20	0.13939 (17)	0.23113 (17)	0.43590 (17)	0.0499 (5)
C21	0.07626 (19)	0.13984 (17)	0.5408 (2)	0.0659 (6)
H21	0.0698	0.0693	0.5355	0.079*
C22	0.0227 (2)	0.1477 (2)	0.6522 (2)	0.0756 (6)
H22	−0.0191	0.0838	0.7198	0.091*
C23	0.0310 (2)	0.2494 (2)	0.6637 (2)	0.0717 (7)
C24	0.0927 (2)	0.34239 (18)	0.56205 (19)	0.0665 (6)
H24	0.0978	0.4124	0.5689	0.080*
C25	0.23720 (19)	0.73914 (17)	−0.09427 (15)	0.0519 (5)
C26	0.2008 (2)	0.21503 (18)	0.31614 (18)	0.0629 (5)
C27	0.2373 (2)	0.79766 (17)	−0.23541 (15)	0.0765 (6)
H27A	0.2133	0.7405	−0.2545	0.115*
H27B	0.3295	0.8131	−0.2800	0.115*
H27C	0.1692	0.8760	−0.2600	0.115*
C28	0.08905 (19)	0.71504 (18)	−0.02588 (17)	0.0797 (7)
H28A	0.0647	0.6608	−0.0487	0.120*
H28B	0.0219	0.7940	−0.0489	0.120*
H28C	0.0878	0.6752	0.0628	0.120*
C29	0.3438 (2)	0.61238 (15)	−0.06099 (16)	0.0699 (6)
H29A	0.3175	0.5603	−0.0853	0.105*
H29B	0.3440	0.5703	0.0276	0.105*
H29C	0.4365	0.6273	−0.1044	0.105*
C30	0.3615 (2)	0.1955 (2)	0.2940 (2)	0.1053 (8)
H30A	0.4003	0.1855	0.2184	0.158*
H30B	0.3983	0.1211	0.3632	0.158*
H30C	0.3869	0.2677	0.2865	0.158*
C31	0.1421 (2)	0.33014 (19)	0.20334 (17)	0.0930 (7)
H31A	0.1826	0.3173	0.1294	0.139*
H31B	0.1656	0.4043	0.1932	0.139*
H31C	0.0413	0.3410	0.2167	0.139*
C32	0.1652 (2)	0.09977 (19)	0.3219 (2)	0.0984 (8)
H32A	0.2059	0.0936	0.2445	0.148*
H32B	0.0645	0.1098	0.3350	0.148*
H32C	0.2031	0.0243	0.3896	0.148*
N1	0.26365 (15)	0.67005 (15)	0.16129 (13)	0.0526 (4)
N2	0.19586 (17)	0.44176 (13)	0.34750 (13)	0.0545 (4)
H23	−0.0036 (17)	0.2586 (14)	0.7406 (15)	0.077 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0590 (15)	0.0515 (14)	0.0470 (12)	−0.0150 (11)	−0.0098 (11)	−0.0246 (11)
C2	0.0603 (14)	0.0464 (13)	0.0476 (12)	−0.0128 (12)	−0.0106 (11)	−0.0220 (11)
C3	0.0620 (15)	0.0531 (14)	0.0510 (13)	−0.0051 (13)	−0.0178 (12)	−0.0255 (12)
C4	0.0534 (15)	0.0582 (15)	0.0639 (14)	−0.0006 (13)	−0.0151 (13)	−0.0410 (13)
C5	0.0519 (15)	0.0527 (14)	0.0637 (14)	−0.0147 (12)	−0.0042 (12)	−0.0355 (12)
C6	0.0616 (16)	0.0692 (16)	0.0895 (16)	−0.0187 (14)	−0.0046 (14)	−0.0475 (13)
C7	0.0604 (19)	0.102 (2)	0.131 (2)	−0.0234 (16)	0.0007 (16)	−0.081 (2)
C8	0.0552 (17)	0.114 (2)	0.135 (2)	0.0018 (18)	−0.0235 (18)	−0.095 (2)
C9	0.0625 (19)	0.085 (2)	0.0918 (19)	0.0030 (17)	−0.0241 (16)	−0.0637 (17)
C10	0.074 (2)	0.106 (2)	0.099 (2)	0.0239 (17)	−0.0439 (17)	−0.070 (2)
C11	0.094 (2)	0.087 (2)	0.0741 (17)	0.0171 (18)	−0.0405 (17)	−0.0409 (15)
C12	0.0810 (18)	0.0700 (17)	0.0610 (14)	−0.0009 (13)	−0.0252 (13)	−0.0306 (13)
C13	0.0505 (12)	0.0440 (13)	0.0474 (12)	−0.0133 (10)	−0.0054 (9)	−0.0166 (11)
C14	0.0463 (12)	0.0420 (12)	0.0493 (12)	−0.0056 (10)	−0.0086 (10)	−0.0179 (11)
C15	0.0772 (15)	0.0567 (14)	0.0542 (13)	−0.0144 (12)	−0.0136 (11)	−0.0216 (12)
C16	0.0986 (18)	0.0529 (14)	0.0649 (15)	−0.0220 (13)	−0.0146 (13)	−0.0152 (13)
C17	0.0955 (17)	0.0526 (15)	0.0803 (15)	−0.0278 (12)	−0.0167 (13)	−0.0285 (13)
C18	0.0853 (15)	0.0587 (14)	0.0577 (13)	−0.0263 (12)	−0.0113 (11)	−0.0253 (12)
C19	0.0511 (13)	0.0417 (13)	0.0487 (12)	−0.0107 (10)	−0.0096 (10)	−0.0124 (11)
C20	0.0425 (12)	0.0440 (12)	0.0571 (13)	−0.0100 (10)	−0.0073 (10)	−0.0174 (11)
C21	0.0640 (15)	0.0515 (14)	0.0719 (15)	−0.0175 (11)	−0.0094 (12)	−0.0169 (13)
C22	0.0644 (15)	0.0648 (17)	0.0693 (16)	−0.0176 (12)	−0.0058 (12)	−0.0082 (13)
C23	0.0690 (16)	0.0757 (18)	0.0520 (15)	−0.0042 (14)	−0.0064 (12)	−0.0224 (15)
C24	0.0809 (16)	0.0569 (14)	0.0582 (13)	−0.0100 (12)	−0.0130 (12)	−0.0241 (12)
C25	0.0524 (13)	0.0535 (13)	0.0515 (12)	−0.0087 (11)	−0.0116 (10)	−0.0240 (11)
C26	0.0602 (15)	0.0613 (14)	0.0761 (15)	−0.0225 (11)	−0.0038 (12)	−0.0349 (12)
C27	0.0948 (16)	0.0786 (15)	0.0643 (14)	−0.0084 (12)	−0.0275 (12)	−0.0353 (12)
C28	0.0692 (16)	0.1032 (18)	0.0887 (15)	−0.0307 (13)	−0.0112 (12)	−0.0518 (14)
C29	0.0849 (16)	0.0529 (13)	0.0719 (13)	−0.0028 (12)	−0.0164 (11)	−0.0321 (11)
C30	0.0646 (17)	0.149 (2)	0.139 (2)	−0.0252 (15)	0.0108 (15)	−0.1028 (19)
C31	0.130 (2)	0.0931 (18)	0.0710 (15)	−0.0391 (16)	−0.0202 (14)	−0.0355 (14)
C32	0.117 (2)	0.0886 (17)	0.1186 (19)	−0.0389 (15)	−0.0052 (15)	−0.0640 (15)
N1	0.0646 (12)	0.0513 (11)	0.0452 (9)	−0.0199 (10)	−0.0116 (9)	−0.0176 (9)
N2	0.0655 (12)	0.0464 (11)	0.0532 (10)	−0.0191 (9)	−0.0117 (9)	−0.0174 (9)

Geometric parameters (Å, º)

C1—N1	1.2692 (19)	C20—C21	1.384 (2)
C1—C5	1.474 (2)	C20—C26	1.522 (2)
C1—C2	1.524 (2)	C21—C22	1.372 (2)
C2—N2	1.271 (2)	C21—H21	0.9300
C2—C3	1.474 (2)	C22—C23	1.364 (3)
C3—C12	1.366 (2)	C22—H22	0.9300
C3—C4	1.406 (2)	C23—C24	1.373 (2)
C4—C9	1.398 (2)	C23—N1^i	3.333 (3)
C4—C5	1.405 (2)	C23—H23	0.968 (15)
C5—C6	1.365 (2)	C24—H24	0.9300
C6—C7	1.412 (3)	C25—C28	1.533 (2)
C6—H6	0.9300	C25—C27	1.535 (2)
C7—C8	1.358 (3)	C25—C29	1.536 (2)
C7—H7	0.9300	C26—C30	1.526 (2)
C8—C9	1.412 (3)	C26—C31	1.531 (2)
C8—H8	0.9300	C26—C32	1.542 (2)
C9—C10	1.405 (3)	C27—H27A	0.9600
C10—C11	1.358 (3)	C27—H27B	0.9600
C10—H10	0.9300	C27—H27C	0.9600
C11—C12	1.408 (3)	C28—N1	3.050 (2)
C11—H11	0.9300	C28—H28A	0.9600
C12—H12	0.9300	C28—H28B	0.9600
C13—C18	1.389 (2)	C28—H28C	0.9600
C13—C14	1.402 (2)	C29—N1	3.010 (2)
C13—N1	1.4187 (19)	C29—H29A	0.9600
C14—C15	1.387 (2)	C29—H29B	0.9600
C14—C25	1.524 (2)	C29—H29C	0.9600
C15—C16	1.380 (2)	C30—H30A	0.9600
C15—H15	0.9300	C30—H30B	0.9600
C16—C17	1.360 (2)	C30—H30C	0.9600
C16—H16	0.9300	C31—N2	2.976 (2)
C17—C18	1.373 (2)	C31—H31A	0.9600
C17—H17	0.9300	C31—H31B	0.9600
C18—H18	0.9300	C31—H31C	0.9600
C19—C24	1.385 (2)	C32—H32A	0.9600
C19—C20	1.402 (2)	C32—H32B	0.9600
C19—N2	1.4178 (19)	C32—H32C	0.9600
N1—C1—C5	134.72 (18)	C14—C25—C27	112.17 (15)
N1—C1—C2	119.00 (18)	C28—C25—C27	108.18 (15)
C5—C1—C2	106.24 (17)	C14—C25—C29	111.31 (15)
N2—C2—C3	133.50 (18)	C28—C25—C29	109.42 (15)
N2—C2—C1	119.94 (18)	C27—C25—C29	106.54 (14)
C3—C2—C1	106.31 (17)	C20—C26—C30	109.44 (16)
C12—C3—C4	119.1 (2)	C20—C26—C31	111.36 (15)
C12—C3—C2	134.1 (2)	C30—C26—C31	109.69 (18)
C4—C3—C2	106.60 (18)	C20—C26—C32	112.48 (16)
C9—C4—C3	122.8 (2)	C30—C26—C32	107.58 (16)
C9—C4—C5	123.4 (2)	C31—C26—C32	106.17 (16)
C3—C4—C5	113.8 (2)	C25—C27—H27A	109.5
C6—C5—C4	119.2 (2)	C25—C27—H27B	109.5
C6—C5—C1	134.0 (2)	H27A—C27—H27B	109.5
C4—C5—C1	106.69 (18)	C25—C27—H27C	109.5
C5—C6—C7	118.5 (2)	H27A—C27—H27C	109.5
C5—C6—H6	120.8	H27B—C27—H27C	109.5
C7—C6—H6	120.8	C25—C28—N1	70.73 (10)
C8—C7—C6	122.2 (2)	C25—C28—H28A	109.5
C8—C7—H7	118.9	N1—C28—H28A	134.2
C6—C7—H7	118.9	C25—C28—H28B	109.5
C7—C8—C9	121.0 (2)	N1—C28—H28B	113.3
C7—C8—H8	119.5	H28A—C28—H28B	109.5
C9—C8—H8	119.5	C25—C28—H28C	109.5
C4—C9—C10	116.6 (2)	H28A—C28—H28C	109.5
C4—C9—C8	115.8 (2)	H28B—C28—H28C	109.5
C10—C9—C8	127.5 (3)	C25—C29—N1	72.04 (9)
C11—C10—C9	120.4 (2)	C25—C29—H29A	109.5
C11—C10—H10	119.8	N1—C29—H29A	136.4
C9—C10—H10	119.8	C25—C29—H29B	109.5
C10—C11—C12	122.5 (2)	H29A—C29—H29B	109.5
C10—C11—H11	118.7	C25—C29—H29C	109.5
C12—C11—H11	118.7	N1—C29—H29C	110.7
C3—C12—C11	118.5 (2)	H29A—C29—H29C	109.5
C3—C12—H12	120.8	H29B—C29—H29C	109.5
C11—C12—H12	120.8	C26—C30—H30A	109.5
C18—C13—C14	121.09 (17)	C26—C30—H30B	109.5
C18—C13—N1	118.71 (16)	H30A—C30—H30B	109.5
C14—C13—N1	119.75 (16)	C26—C30—H30C	109.5
C15—C14—C13	115.71 (16)	H30A—C30—H30C	109.5
C15—C14—C25	121.64 (16)	H30B—C30—H30C	109.5
C13—C14—C25	122.58 (16)	C26—C31—N2	76.07 (10)
C16—C15—C14	123.15 (18)	C26—C31—H31A	109.5
C16—C15—H15	118.4	N2—C31—H31A	139.8
C14—C15—H15	118.4	C26—C31—H31B	109.5
C17—C16—C15	119.76 (19)	H31A—C31—H31B	109.5
C17—C16—H16	120.1	C26—C31—H31C	109.5
C15—C16—H16	120.1	N2—C31—H31C	105.3
C16—C17—C18	119.52 (18)	H31A—C31—H31C	109.5
C16—C17—H17	120.2	H31B—C31—H31C	109.5
C18—C17—H17	120.2	C26—C32—H32A	109.5
C17—C18—C13	120.68 (17)	C26—C32—H32B	109.5
C17—C18—H18	119.7	H32A—C32—H32B	109.5
C13—C18—H18	119.7	C26—C32—H32C	109.5
C24—C19—C20	120.40 (17)	H32A—C32—H32C	109.5
C24—C19—N2	116.80 (17)	H32B—C32—H32C	109.5
C20—C19—N2	122.43 (16)	C1—N1—C13	123.03 (16)
C21—C20—C19	115.78 (17)	C1—N1—H29B	92.7
C21—C20—C26	121.07 (18)	C13—N1—H29B	94.2
C19—C20—C26	123.11 (17)	C1—N1—H28C	140.3
C22—C21—C20	123.55 (19)	C13—N1—H28C	91.9
C22—C21—H21	118.2	H29B—N1—H28C	64.2
C20—C21—H21	118.2	C1—N1—C29	105.62 (11)
C23—C22—C21	119.9 (2)	C13—N1—C29	80.55 (9)
C23—C22—H22	120.1	H28C—N1—C29	58.5
C21—C22—H22	120.1	C1—N1—C28	146.13 (12)
C22—C23—C24	118.6 (2)	C13—N1—C28	79.23 (10)
C22—C23—N1^i	109.37 (16)	H29B—N1—C28	57.9
C24—C23—N1^i	119.39 (15)	C29—N1—C28	48.82 (5)
C22—C23—H23	123.1 (10)	C2—N2—C19	122.07 (16)
C24—C23—H23	118.3 (10)	C2—N2—H31B	121.2
C23—C24—C19	121.7 (2)	C19—N2—H31B	96.2
C23—C24—H24	119.1	C2—N2—C31	128.81 (12)
C19—C24—H24	119.1	C19—N2—C31	81.48 (11)
C14—C25—C28	109.13 (14)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···N1^i	0.97 (2)	2.62 (2)	3.331 (3)	130.6 (17)
C28—H28C···N1	0.96	2.40	3.048 (3)	125
C29—H29B···N1	0.96	2.35	3.010 (3)	125
C31—H31B···N2	0.96	2.30	2.975 (3)	127

Symmetry code: (i) −x, −y+1, −z+1.