5,15-Bis(3,5-di-tert-butyl-phen-yl)-10,20-bis-(phenyl-ethyn-yl)porphyrin.

In the centrosymmetric title compound, C(64)H(62)N(4), the two phenyl-ethynyl groups lie at diagonal meso positions. The 24-membered porphyrin has in-plane distortion with respect to the mean plane of the macrocycle and two intra-ring bifurcated N-H⋯(N,N) hydrogen bonds occur. The dihedral angles between the phenyl rings in the phenyl-ethynyl group and the 3,5-bis-(tert-but-yl)phenyl group with respect to the mean plane of the porphyrin are 17.2 (2) and 59.2 (3)°. The tert-butyl groups are disordered over two sets of sites in a 0.661 (13):0.339 (13) ratio.

Related literature

For background to porphyrin structures and electronic properties, see: Anderson et al. (1994 ▶, 1998 ▶); Fujita et al. (1995 ▶); Henari et al. (1997 ▶); Huuskonen et al. (1998 ▶); LeCours et al. (1996 ▶); Screen et al. (2002 ▶); Seo et al. (2008 ▶); Silvers & Tulinsky (1967 ▶).

Experimental

Crystal data

C64H62N4

M = 887.18

Triclinic,

a = 9.9598 (19) Å

b = 10.496 (2) Å

c = 13.925 (3) Å

α = 86.236 (4)°

β = 80.266 (4)°

γ = 82.765 (4)°

V = 1421.8 (5) Å3

Z = 1

Mo Kα radiation

μ = 0.06 mm−1

T = 213 K

0.45 × 0.10 × 0.05 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.974, T max = 0.997

6144 measured reflections

4136 independent reflections

2068 reflections with I > 2σ(I)

R int = 0.101

θmax = 23.5°

Refinement

R[F 2 > 2σ(F 2)] = 0.107

wR(F 2) = 0.315

S = 0.99

4136 reflections

363 parameters

193 restraints

H-atom parameters constrained

Δρmax = 1.13 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045954/hb5134sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045954/hb5134Isup2.hkl

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

C64H62N4	Z = 1
Mr = 887.18	F(000) = 474
Triclinic, P1	Dx = 1.036 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9598 (19) Å	Cell parameters from 4136 reflections
b = 10.496 (2) Å	θ = 2.0–23.5°
c = 13.925 (3) Å	µ = 0.06 mm−1
α = 86.236 (4)°	T = 213 K
β = 80.266 (4)°	Needle, purple
γ = 82.765 (4)°	0.45 × 0.10 × 0.05 mm
V = 1421.8 (5) Å3

Bruker SMART CCD diffractometer	4136 independent reflections
Radiation source: fine-focus sealed tube	2068 reflections with I > 2σ(I)
graphite	Rint = 0.101
ω scans	θmax = 23.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −8→11
Tmin = 0.974, Tmax = 0.997	k = −11→11
6144 measured reflections	l = −11→15

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)] = 0.107	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.315	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.1906P)2] where P = (Fo2 + 2Fc2)/3
4136 reflections	(Δ/σ)max < 0.001
363 parameters	Δρmax = 1.13 e Å−3
193 restraints	Δρmin = −0.30 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.4997 (4)	0.8413 (3)	0.5981 (3)	0.0445 (11)
H1A	0.4940	0.9116	0.5616	0.053*
N2	0.3805 (4)	0.9196 (3)	0.4184 (3)	0.0481 (11)
C1	0.5695 (5)	0.8204 (4)	0.6753 (3)	0.0429 (13)
C2	0.5537 (6)	0.6929 (5)	0.7151 (4)	0.0529 (14)
H2	0.5907	0.6530	0.7689	0.063*
C3	0.4771 (6)	0.6413 (5)	0.6622 (4)	0.0600 (16)
H3	0.4511	0.5578	0.6718	0.072*
C4	0.4409 (5)	0.7342 (4)	0.5880 (4)	0.0449 (13)
C5	0.3646 (5)	0.7155 (4)	0.5160 (4)	0.0482 (13)
C6	0.3377 (5)	0.8019 (5)	0.4380 (4)	0.0468 (13)
C7	0.2576 (6)	0.7764 (5)	0.3646 (4)	0.0577 (15)
H7	0.2154	0.7020	0.3608	0.069*
C8	0.2563 (6)	0.8818 (5)	0.3030 (4)	0.0564 (15)
H8	0.2137	0.8929	0.2472	0.068*
C9	0.3299 (5)	0.9725 (4)	0.3367 (3)	0.0409 (12)
C10	0.3527 (5)	1.0946 (5)	0.2919 (3)	0.0470 (13)
C11	0.3101 (6)	0.5928 (5)	0.5201 (4)	0.0557 (14)
C12	0.2674 (6)	0.4937 (5)	0.5260 (4)	0.0606 (16)
C13	0.2183 (6)	0.3674 (5)	0.5331 (4)	0.0584 (15)
C14	0.2721 (6)	0.2699 (5)	0.5915 (4)	0.0605 (15)
H14	0.3410	0.2849	0.6265	0.073*
C15	0.1152 (6)	0.3433 (5)	0.4811 (4)	0.0626 (16)
H15	0.0781	0.4072	0.4393	0.075*
C16	0.2265 (7)	0.1512 (5)	0.5990 (5)	0.0712 (18)
H16	0.2655	0.0850	0.6381	0.085*
C17	0.0704 (7)	0.2243 (6)	0.4930 (4)	0.0760 (19)
H17	−0.0007	0.2083	0.4605	0.091*
C18	0.1249 (8)	0.1287 (6)	0.5501 (5)	0.0757 (19)
H18	0.0929	0.0475	0.5558	0.091*
C19	0.2853 (6)	1.1365 (5)	0.2057 (4)	0.0511 (14)
C20	0.1439 (6)	1.1470 (5)	0.2137 (4)	0.0636 (16)
H20	0.0914	1.1283	0.2745	0.076*
C21	0.3627 (6)	1.1657 (4)	0.1160 (4)	0.0541 (14)
H21	0.4586	1.1596	0.1104	0.065*
C22	0.0761 (6)	1.1849 (6)	0.1337 (4)	0.0704 (17)
C23	0.3015 (6)	1.2037 (5)	0.0341 (4)	0.0612 (15)
C24	0.1597 (6)	1.2114 (6)	0.0466 (4)	0.0714 (18)
H24	0.1172	1.2366	−0.0081	0.086*
C25	−0.0782 (7)	1.2010 (8)	0.1463 (5)	0.090 (2)
C26A	−0.1491 (10)	1.1396 (11)	0.2354 (9)	0.077 (3)	0.661 (13)
H26A	−0.1029	1.0541	0.2459	0.115*	0.661 (13)
H26B	−0.2433	1.1337	0.2283	0.115*	0.661 (13)
H26C	−0.1479	1.1907	0.2908	0.115*	0.661 (13)
C27A	−0.1397 (14)	1.3240 (12)	0.1232 (13)	0.118 (5)	0.661 (13)
H27A	−0.2385	1.3240	0.1324	0.178*	0.661 (13)
H27B	−0.1063	1.3481	0.0558	0.178*	0.661 (13)
H27C	−0.1171	1.3852	0.1655	0.178*	0.661 (13)
C28A	−0.1218 (15)	1.1113 (16)	0.0638 (12)	0.147 (6)	0.661 (13)
H28A	−0.0845	1.0225	0.0739	0.221*	0.661 (13)
H28B	−0.0852	1.1424	−0.0013	0.221*	0.661 (13)
H28C	−0.2209	1.1172	0.0711	0.221*	0.661 (13)
C26B	−0.125 (4)	1.110 (3)	0.176 (3)	0.156 (15)	0.339 (13)
H26D	−0.2235	1.1246	0.1789	0.234*	0.339 (13)
H26E	−0.1041	1.0889	0.2416	0.234*	0.339 (13)
H26F	−0.0867	1.0400	0.1344	0.234*	0.339 (13)
C27B	−0.121 (3)	1.3362 (18)	0.2041 (19)	0.109 (9)	0.339 (13)
H27D	−0.0753	1.4043	0.1668	0.164*	0.339 (13)
H27E	−0.0933	1.3249	0.2679	0.164*	0.339 (13)
H27F	−0.2195	1.3590	0.2115	0.164*	0.339 (13)
C28B	−0.117 (3)	1.263 (3)	0.048 (2)	0.153 (12)	0.339 (13)
H28D	−0.0526	1.3227	0.0203	0.229*	0.339 (13)
H28E	−0.2091	1.3088	0.0598	0.229*	0.339 (13)
H28F	−0.1147	1.1962	0.0025	0.229*	0.339 (13)
C29	0.3836 (7)	1.2398 (6)	−0.0623 (4)	0.0763 (18)
C30A	0.495 (6)	1.131 (5)	−0.084 (4)	0.094 (9)	0.121 (8)
H30A	0.5050	1.0805	−0.0243	0.141*	0.121 (8)
H30B	0.5801	1.1652	−0.1102	0.141*	0.121 (8)
H30C	0.4709	1.0776	−0.1311	0.141*	0.121 (8)
C31A	0.294 (5)	1.274 (6)	−0.138 (4)	0.089 (10)	0.121 (8)
H31A	0.3509	1.2927	−0.2001	0.134*	0.121 (8)
H31B	0.2299	1.3483	−0.1193	0.134*	0.121 (8)
H31C	0.2446	1.2018	−0.1446	0.134*	0.121 (8)
C32A	0.445 (7)	1.358 (5)	−0.035 (5)	0.110 (10)	0.121 (8)
H32A	0.5169	1.3299	0.0039	0.165*	0.121 (8)
H32B	0.3740	1.4150	0.0026	0.165*	0.121 (8)
H32C	0.4841	1.4041	−0.0938	0.165*	0.121 (8)
C30B	0.3606 (9)	1.1477 (8)	−0.1410 (5)	0.092 (3)	0.879 (8)
H30D	0.4134	1.1703	−0.2035	0.138*	0.879 (8)
H30E	0.2640	1.1563	−0.1463	0.138*	0.879 (8)
H30F	0.3903	1.0595	−0.1217	0.138*	0.879 (8)
C31B	0.3428 (10)	1.3783 (8)	−0.0936 (6)	0.109 (3)	0.879 (8)
H31D	0.3979	1.3990	−0.1557	0.163*	0.879 (8)
H31E	0.3579	1.4346	−0.0449	0.163*	0.879 (8)
H31F	0.2466	1.3899	−0.1003	0.163*	0.879 (8)
C32B	0.5416 (8)	1.2160 (9)	−0.0616 (5)	0.086 (2)	0.879 (8)
H32D	0.5902	1.2415	−0.1249	0.130*	0.879 (8)
H32E	0.5680	1.1255	−0.0475	0.130*	0.879 (8)
H32F	0.5645	1.2664	−0.0120	0.130*	0.879 (8)

	U11	U22	U33	U12	U13	U23
N1	0.048 (3)	0.031 (2)	0.050 (3)	−0.0016 (18)	−0.004 (2)	0.0123 (18)
N2	0.053 (3)	0.039 (2)	0.050 (3)	−0.0027 (19)	−0.002 (2)	0.0033 (19)
C1	0.043 (3)	0.033 (3)	0.046 (3)	0.006 (2)	−0.001 (2)	0.012 (2)
C2	0.057 (4)	0.043 (3)	0.059 (3)	−0.008 (3)	−0.014 (3)	0.014 (3)
C3	0.058 (4)	0.047 (3)	0.071 (4)	−0.009 (3)	−0.006 (3)	0.026 (3)
C4	0.050 (3)	0.032 (3)	0.048 (3)	−0.005 (2)	0.005 (3)	0.006 (2)
C5	0.049 (3)	0.041 (3)	0.051 (3)	−0.007 (2)	−0.002 (3)	0.006 (2)
C6	0.035 (3)	0.050 (3)	0.051 (3)	−0.001 (2)	0.001 (2)	−0.002 (2)
C7	0.061 (4)	0.055 (3)	0.059 (4)	−0.021 (3)	−0.006 (3)	0.004 (3)
C8	0.061 (4)	0.066 (4)	0.043 (3)	−0.014 (3)	−0.006 (3)	0.000 (3)
C9	0.035 (3)	0.039 (3)	0.046 (3)	0.000 (2)	−0.004 (2)	0.001 (2)
C10	0.043 (3)	0.050 (3)	0.043 (3)	0.003 (2)	0.000 (2)	−0.001 (2)
C11	0.059 (4)	0.046 (3)	0.060 (4)	−0.014 (3)	−0.004 (3)	0.011 (3)
C12	0.071 (4)	0.046 (3)	0.062 (4)	−0.012 (3)	−0.001 (3)	0.008 (3)
C13	0.056 (4)	0.043 (3)	0.071 (4)	−0.009 (3)	0.007 (3)	−0.008 (3)
C14	0.055 (4)	0.049 (3)	0.075 (4)	−0.007 (3)	−0.004 (3)	−0.001 (3)
C15	0.071 (4)	0.054 (3)	0.059 (4)	−0.006 (3)	−0.004 (3)	0.000 (3)
C16	0.065 (4)	0.044 (3)	0.093 (5)	0.001 (3)	0.009 (4)	0.011 (3)
C17	0.090 (5)	0.084 (5)	0.058 (4)	−0.038 (4)	0.000 (3)	−0.014 (3)
C18	0.080 (5)	0.055 (4)	0.085 (5)	−0.020 (3)	0.016 (4)	−0.008 (4)
C19	0.053 (4)	0.052 (3)	0.046 (3)	0.003 (3)	−0.008 (3)	−0.005 (2)
C20	0.049 (4)	0.076 (4)	0.057 (4)	0.011 (3)	0.004 (3)	−0.001 (3)
C21	0.054 (4)	0.053 (3)	0.049 (3)	0.007 (3)	−0.002 (3)	−0.003 (2)
C22	0.057 (4)	0.086 (4)	0.061 (4)	0.020 (3)	−0.010 (3)	0.000 (3)
C23	0.062 (4)	0.062 (3)	0.057 (4)	0.011 (3)	−0.018 (3)	0.004 (3)
C24	0.063 (5)	0.095 (4)	0.050 (4)	0.024 (3)	−0.015 (3)	0.000 (3)
C25	0.054 (5)	0.121 (6)	0.086 (5)	0.029 (4)	−0.020 (4)	0.009 (4)
C26A	0.038 (5)	0.093 (6)	0.096 (7)	−0.002 (4)	−0.014 (5)	0.018 (5)
C27A	0.097 (8)	0.117 (8)	0.135 (9)	0.002 (6)	−0.020 (7)	0.011 (7)
C28A	0.109 (9)	0.171 (10)	0.167 (10)	−0.024 (7)	−0.031 (7)	−0.014 (8)
C26B	0.149 (17)	0.162 (17)	0.157 (17)	−0.013 (10)	−0.031 (10)	0.002 (10)
C27B	0.099 (11)	0.111 (11)	0.114 (12)	−0.006 (8)	−0.015 (9)	0.000 (9)
C28B	0.147 (15)	0.165 (15)	0.148 (14)	−0.006 (9)	−0.037 (9)	−0.006 (9)
C29	0.081 (4)	0.089 (4)	0.048 (3)	0.016 (3)	−0.002 (3)	0.004 (3)
C30A	0.089 (12)	0.096 (11)	0.092 (13)	0.003 (8)	−0.010 (9)	0.002 (9)
C31A	0.087 (12)	0.095 (14)	0.085 (12)	−0.007 (8)	−0.015 (9)	0.005 (9)
C32A	0.112 (15)	0.112 (12)	0.106 (15)	−0.011 (9)	−0.021 (10)	−0.012 (10)
C30B	0.083 (5)	0.133 (6)	0.052 (4)	0.007 (4)	0.000 (3)	−0.010 (4)
C31B	0.114 (6)	0.108 (5)	0.089 (5)	−0.002 (4)	0.002 (5)	0.039 (4)
C32B	0.083 (5)	0.122 (6)	0.045 (4)	0.001 (4)	0.003 (3)	0.009 (4)

N1—C4	1.357 (6)	C29—C30A	1.49 (4)
N1—C1	1.367 (6)	C29—C31A	1.49 (4)
N2—C6	1.354 (6)	C29—C31B	1.515 (9)
N2—C9	1.378 (6)	C29—C30B	1.570 (10)
C1—C10i	1.397 (7)	C29—C32B	1.563 (10)
C1—C2	1.431 (6)	C29—C32A	1.55 (5)
C2—C3	1.329 (7)	N1—H1A	0.869 (3)
C3—C4	1.433 (7)	C2—H2	0.941 (6)
C4—C5	1.393 (7)	C3—H3	0.940 (5)
C5—C6	1.407 (7)	C8—H8	0.940 (6)
C5—C11	1.454 (7)	C14—H14	0.940 (6)
C6—C7	1.455 (7)	C15—H15	0.940 (5)
C7—C8	1.355 (7)	C16—H16	0.940 (6)
C8—C9	1.420 (7)	C17—H17	0.940 (7)
C9—C10	1.415 (6)	C18—H18	0.941 (7)
C10—C1i	1.397 (7)	C20—H20	0.940 (5)
C10—C19	1.488 (7)	C21—H21	0.939 (6)
C11—C12	1.164 (7)	C24—H24	0.940 (6)
C12—C13	1.462 (7)	C26A—H26A	0.97 (1)
C13—C14	1.377 (8)	C26A—H26B	0.97 (1)
C13—C15	1.409 (8)	C26A—H26C	0.97 (1)
C14—C16	1.371 (7)	C27A—H27A	0.97 (1)
C15—C17	1.369 (8)	C27A—H27B	0.97 (2)
C16—C18	1.364 (9)	C27A—H27C	0.97 (2)
C17—C18	1.355 (9)	C28A—H28A	0.97 (2)
C19—C20	1.385 (7)	C28A—H28B	0.97 (2)
C19—C21	1.390 (7)	C28A—H28C	0.97 (1)
C20—C22	1.408 (8)	C30A—H30A	0.97 (5)
C21—C23	1.395 (7)	C30A—H30B	0.97 (6)
C22—C24	1.383 (8)	C30A—H30C	0.97 (6)
C22—C25	1.506 (9)	C31A—H31A	0.97 (5)
C23—C24	1.386 (8)	C31A—H31B	0.96 (5)
C23—C29	1.502 (8)	C31A—H31C	0.97 (6)
C25—C26B	1.14 (3)	C32A—H32A	0.97 (7)
C25—C27A	1.400 (13)	C32A—H32B	0.97 (6)
C25—C26A	1.473 (12)	C32A—H32C	0.97 (6)
C25—C28B	1.57 (3)	N1—H1A	0.869 (3)
C25—C27B	1.651 (16)	C2—H2	0.941 (6)
C25—C28A	1.676 (16)
C4—N1—C1	108.7 (4)	C28B—C25—C28A	59.0 (12)
C6—N2—C9	107.9 (4)	C27B—C25—C28A	143.9 (12)
N1—C1—C10i	126.7 (4)	C30A—C29—C31A	116 (3)
N1—C1—C2	107.9 (5)	C30A—C29—C23	106 (2)
C10i—C1—C2	125.4 (5)	C31A—C29—C23	112 (2)
C3—C2—C1	107.4 (5)	C30A—C29—C31B	142 (2)
C2—C3—C4	108.6 (5)	C31A—C29—C31B	58 (2)
N1—C4—C5	126.4 (4)	C23—C29—C31B	111.3 (5)
N1—C4—C3	107.4 (5)	C30A—C29—C30B	65 (2)
C5—C4—C3	126.1 (5)	C31A—C29—C30B	54 (2)
C4—C5—C6	126.8 (4)	C23—C29—C30B	109.0 (6)
C4—C5—C11	116.8 (4)	C31B—C29—C30B	110.0 (6)
C6—C5—C11	116.4 (5)	C30A—C29—C32B	44 (2)
N2—C6—C5	126.7 (5)	C31A—C29—C32B	136 (2)
N2—C6—C7	109.1 (4)	C23—C29—C32B	112.4 (5)
C5—C6—C7	124.2 (5)	C31B—C29—C32B	110.1 (7)
C8—C7—C6	105.9 (5)	C30B—C29—C32B	103.9 (6)
C7—C8—C9	108.7 (5)	C30A—C29—C32A	110 (3)
N2—C9—C8	108.4 (4)	C31A—C29—C32A	112 (3)
N2—C9—C10	125.5 (5)	C23—C29—C32A	101 (2)
C8—C9—C10	126.0 (5)	C31B—C29—C32A	54 (2)
C1i—C10—C9	124.6 (5)	C30B—C29—C32A	150 (2)
C1i—C10—C19	117.9 (4)	C32B—C29—C32A	66 (2)
C9—C10—C19	117.4 (5)	C25—C26A—H26A	110 (1)
C12—C11—C5	178.0 (6)	C25—C26A—H26B	109 (1)
C11—C12—C13	178.2 (6)	C25—C26A—H26C	109 (1)
C14—C13—C15	118.9 (5)	H26A—C26A—H26B	109 (1)
C14—C13—C12	120.2 (6)	H26A—C26A—H26C	109 (1)
C15—C13—C12	120.9 (5)	H26B—C26A—H26C	109 (1)
C16—C14—C13	120.7 (6)	C25—C27A—H27A	109 (1)
C17—C15—C13	118.2 (6)	C25—C27A—H27B	110 (1)
C18—C16—C14	120.3 (6)	C25—C27A—H27C	109 (1)
C18—C17—C15	122.4 (7)	H27A—C27A—H27B	109 (1)
C17—C18—C16	119.4 (6)	H27A—C27A—H27C	109 (1)
C20—C19—C21	118.9 (5)	H27B—C27A—H27C	109 (1)
C20—C19—C10	120.3 (5)	C25—C28A—H28A	109 (1)
C21—C19—C10	120.8 (5)	C25—C28A—H28B	109 (1)
C19—C20—C22	122.2 (5)	C25—C28A—H28C	109 (1)
C23—C21—C19	121.6 (5)	H28A—C28A—H28B	109 (2)
C24—C22—C20	115.8 (6)	H28A—C28A—H28C	110 (2)
C24—C22—C25	123.6 (6)	H28B—C28A—H28C	109 (2)
C20—C22—C25	120.6 (5)	C23—C29—C30A	106 (2)
C24—C23—C21	116.7 (5)	C23—C29—C31A	111 (2)
C24—C23—C29	121.1 (5)	C23—C29—C32A	101 (2)
C21—C23—C29	122.1 (6)	C30A—C29—C31A	116 (3)
C22—C24—C23	124.8 (6)	C30A—C29—C32A	110 (3)
C26B—C25—C27A	131 (2)	C31A—C29—C32A	112 (3)
C26B—C25—C26A	36.7 (19)	C29—C30A—H30A	109 (5)
C27A—C25—C26A	113.9 (9)	C29—C30A—H30B	109 (5)
C26B—C25—C22	113 (2)	C29—C30A—H30C	109 (5)
C27A—C25—C22	115.8 (9)	H30A—C30A—H30B	110 (5)
C26A—C25—C22	115.9 (6)	H30A—C30A—H30C	110 (5)
C26B—C25—C28B	117 (2)	H30B—C30A—H30C	110 (5)
C27A—C25—C28B	48.9 (12)	C29—C31A—H31A	109 (5)
C26A—C25—C28B	136.7 (14)	C29—C31A—H31B	110 (5)
C22—C25—C28B	106.5 (13)	C29—C31A—H31C	109 (5)
C26B—C25—C27B	120 (2)	H31A—C31A—H31B	110 (5)
C27A—C25—C27B	45.0 (9)	H31A—C31A—H31C	109 (5)
C26A—C25—C27B	85.5 (11)	H31B—C31A—H31C	110 (5)
C22—C25—C27B	102.9 (11)	C29—C32A—H32A	110 (5)
C28B—C25—C27B	93.6 (14)	C29—C32A—H32B	110 (5)
C26B—C25—C28A	64 (2)	C29—C32A—H32C	110 (5)
C27A—C25—C28A	102.6 (10)	H32A—C32A—H32B	109 (6)
C26A—C25—C28A	98.7 (9)	H32A—C32A—H32C	109 (6)
C22—C25—C28A	107.1 (7)	H32B—C32A—H32C	109 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2	0.87	2.44	2.972 (6)	120
N1—H1A···N2i	0.87	2.35	2.891 (5)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2	0.87	2.44	2.972 (6)	120
N1—H1A⋯N2i	0.87	2.35	2.891 (5)	121

Symmetry code: (i) .