A synchrotron study of [5,10,15,20-tetra­kis­(3-cyano­phen­yl)porphyrinato-[kappa]⁴N⁵,N¹⁰,N¹⁵,N²⁰]copper(II) nitro­benzene tris­olvate at 80 K

Porphyrin assemblies display inter­esting photophysical properties and a relatively high thermal stability. Moreover, meso-functionalized porphyrins with virtually fourfold symmetry can be relatively readily synthesized from pyrrole and the appropriate aldehyde. A number of metallo derivatives of 5,10,15,20-tetra­kis­(4-cyano­phen­yl)porphyrin, where the N atom of the linear cyano group can act both as a donor for coordination bonds or as an acceptor for hydrogen bonds, have been structurally characterized by single-crystal X-ray analysis. The supra­molecular and structural chemistry of the corresponding 2- and 3-cyano­phenyl isomers of the parent porphyrin, however, has remained largely unexplored. The crystal structure of [5,10,15,20-tetra­kis­(3-cyano­phen­yl)porphyrinato]copper(II) (CuTCNPP) nitro­benzene tris­olvate, [Cu(C₄₈H₂₄N₈)]·3C₆H₅NO₂, has been determined at 80 K by synchrotron single-crystal X-ray diffraction. CuTCNPP exhibits a C_2h-symmetric [alpha][alpha][beta][beta] conformation, despite an unsymmetrical crystal environment, and is situated on a crystallographic centre of symmetry. The Cu^II ion adopts a genuine square-planar coordination by the four pyrrole N atoms. The 24-membered porphyrin ring system shows no marked deviation from planarity. In the crystal, the CuTCNPP mol­ecules and two nitro­benzene mol­ecules are face-to-face stacked in an alternating fashion, resulting in corrugated layers. The remaining nitro­benzene guest mol­ecule per CuTCNPP resides in the region between four neighbouring columnar stacks of CuTCNPP and sandwiched nitro­benzene mol­ecules, and is disordered over four positions about a centre of symmetry.

Computing details

Data collection: P11 Crystallography Control (Meents et al., 2013); cell refinement: XDS (Kabsch, 2010); data reduction: XDS (Kabsch, 2010); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007) and EDMA (Palatinus et al., 2012)'; program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2014); software used to prepare material for publication: enCIFer (Allen et al., 2004).

5,10,15,20-tetrakis(3-cyanophenyl)porphyrinatocopper(II) nitrobenzene trisolvate

Crystal data

[Cu(C48H24N8)]·3C6H5NO2	Z = 1
Mr = 1145.62	F(000) = 589
Triclinic, P1	Dx = 1.434 Mg m^−3
a = 8.234 (4) Å	Synchrotron radiation, λ = 0.56305 Å
b = 11.872 (9) Å	Cell parameters from 34070 reflections
c = 14.212 (7) Å	θ = 1.2–23.7°
α = 104.37 (3)°	µ = 0.26 mm^−1
β = 94.85 (10)°	T = 80 K
γ = 96.85 (8)°	Prism, purple
V = 1326.8 (14) Å^3	0.04 × 0.01 × 0.01 mm

Data collection

P11 beamline at PETRA III with Pilatus 6M detector (Kraft et al., 2009) diffractometer	7802 independent reflections
Radiation source: synchrotron	7176 reflections with I > 2σ(I)
Detector resolution: 5.81 pixels mm^-1	Rint = 0.038
φ scans	θmax = 23.7°, θmin = 1.2°
Absorption correction: multi-scan (XDS; Kabsch, 2010)	h = −11→11
Tmin = 0.918, Tmax = 1.000	k = −16→16
43137 measured reflections	l = −20→20

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.130	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0494P)^2 + 2.9063P] where P = (Fo^2 + 2Fc^2)/3
7802 reflections	(Δ/σ)max < 0.001
389 parameters	Δρmax = 0.97 e Å^−3
60 restraints	Δρmin = −1.13 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cu1	0.0000	0.5000	0.5000	0.00671 (8)
N1	0.6994 (2)	0.32906 (15)	0.95871 (12)	0.0144 (3)
N2	0.5750 (2)	−0.08604 (15)	0.23767 (14)	0.0190 (3)
N21	0.02618 (18)	0.58412 (12)	0.64199 (10)	0.0059 (2)
N22	0.09972 (18)	0.36511 (12)	0.53325 (10)	0.0066 (2)
C1	−0.0107 (2)	0.69490 (14)	0.68306 (12)	0.0070 (3)
C2	0.0317 (2)	0.72614 (15)	0.78785 (12)	0.0105 (3)
H2	0.0167	0.7971	0.8327	0.013*
C3	0.0970 (2)	0.63481 (15)	0.81011 (12)	0.0093 (3)
H3	0.1386	0.6304	0.8733	0.011*
C4	0.0909 (2)	0.54588 (14)	0.71940 (11)	0.0065 (3)
C5	0.1438 (2)	0.43677 (14)	0.71330 (11)	0.0061 (3)
C6	0.1465 (2)	0.35264 (14)	0.62531 (12)	0.0073 (3)
C7	0.1955 (2)	0.23842 (15)	0.61857 (13)	0.0114 (3)
H7	0.2324	0.2086	0.6715	0.014*
C8	0.1785 (2)	0.18180 (15)	0.52180 (13)	0.0121 (3)
H8	0.2018	0.1048	0.4942	0.014*
C9	0.1184 (2)	0.26042 (14)	0.46891 (12)	0.0081 (3)
C10	0.0780 (2)	0.23160 (14)	0.36749 (12)	0.0071 (3)
C51	0.3989 (2)	0.36336 (14)	0.91937 (12)	0.0074 (3)
C52	0.3537 (2)	0.38807 (14)	0.83029 (12)	0.0077 (3)
H52	0.4323	0.3912	0.7854	0.009*
C53	0.1939 (2)	0.40814 (13)	0.80724 (11)	0.0063 (3)
C54	0.0792 (2)	0.40126 (14)	0.87430 (12)	0.0074 (3)
H54	−0.0307	0.4138	0.8591	0.009*
C55	0.1251 (2)	0.37619 (15)	0.96280 (12)	0.0090 (3)
H55	0.0461	0.3717	1.0072	0.011*
C56	0.2850 (2)	0.35780 (15)	0.98655 (12)	0.0094 (3)
H56	0.3166	0.3418	1.0472	0.011*
C57	0.5659 (2)	0.34414 (15)	0.94157 (12)	0.0101 (3)
C101	0.2809 (2)	−0.02879 (14)	0.24570 (12)	0.0085 (3)
C102	0.2607 (2)	0.08212 (14)	0.30248 (12)	0.0082 (3)
H102	0.3541	0.1363	0.3363	0.010*
C103	0.1031 (2)	0.11283 (14)	0.30923 (12)	0.0074 (3)
C104	−0.0328 (2)	0.03053 (14)	0.25935 (12)	0.0090 (3)
H104	−0.1408	0.0502	0.2644	0.011*
C105	−0.0118 (2)	−0.07955 (15)	0.20254 (13)	0.0104 (3)
H105	−0.1053	−0.1341	0.1693	0.012*
C106	0.1452 (2)	−0.10993 (14)	0.19439 (13)	0.0099 (3)
H106	0.1603	−0.1843	0.1548	0.012*
C107	0.4445 (2)	−0.06028 (15)	0.24046 (14)	0.0124 (3)
O1	0.3979 (3)	0.43185 (19)	0.34409 (16)	0.0379 (5)
O2	0.2887 (2)	0.50260 (17)	0.23127 (13)	0.0279 (4)
N3	0.3365 (2)	0.50953 (18)	0.31689 (15)	0.0236 (4)
C11	0.3205 (3)	0.6179 (2)	0.39096 (16)	0.0206 (4)
C12	0.3550 (3)	0.6213 (2)	0.48943 (17)	0.0260 (5)
H12	0.3869	0.5552	0.5086	0.031*
C13	0.3415 (3)	0.7241 (3)	0.55864 (17)	0.0302 (6)
H13	0.3645	0.7289	0.6263	0.036*
C14	0.2944 (3)	0.8202 (2)	0.52978 (18)	0.0308 (5)
H14	0.2863	0.8905	0.5776	0.037*
C15	0.2591 (3)	0.8136 (2)	0.43061 (18)	0.0288 (5)
H15	0.2259	0.8793	0.4112	0.035*
C16	0.2721 (3)	0.7120 (2)	0.36030 (16)	0.0232 (4)
H16	0.2483	0.7070	0.2927	0.028*
O3	0.2297 (14)	0.1246 (8)	0.0730 (7)	0.054 (3)*	0.261 (5)
O4	0.1129 (11)	−0.0405 (8)	−0.0211 (7)	0.047 (2)*	0.261 (5)
N4	0.2302 (11)	0.0300 (8)	0.0159 (7)	0.032 (2)*	0.261 (5)
C21	0.3953 (6)	−0.0015 (6)	−0.0055 (5)	0.0237 (19)*	0.261 (5)
C22	0.4071 (6)	−0.1080 (5)	−0.0709 (4)	0.0148 (16)*	0.261 (5)
H22	0.3100	−0.1594	−0.1029	0.018*	0.261 (5)
C23	0.5609 (9)	−0.1392 (5)	−0.0897 (4)	0.0233 (18)*	0.261 (5)
H23	0.5689	−0.2119	−0.1344	0.028*	0.261 (5)
C24	0.7029 (6)	−0.0639 (7)	−0.0430 (6)	0.0197 (18)*	0.261 (5)
H24	0.8080	−0.0853	−0.0558	0.024*	0.261 (5)
C25	0.6912 (7)	0.0425 (7)	0.0225 (5)	0.034 (2)*	0.261 (5)
H25	0.7883	0.0939	0.0545	0.041*	0.261 (5)
C26	0.5374 (10)	0.0737 (5)	0.0413 (5)	0.035 (2)*	0.261 (5)
H26	0.5294	0.1464	0.0860	0.042*	0.261 (5)
O3'	0.8337 (16)	−0.0624 (14)	−0.0272 (11)	0.077 (4)*	0.239 (5)
O4'	0.6299 (16)	−0.1808 (11)	−0.1247 (9)	0.067 (4)*	0.239 (5)
N4'	0.6860 (16)	−0.0956 (14)	−0.0589 (12)	0.050 (5)*	0.239 (5)
C21'	0.5619 (9)	−0.0248 (7)	−0.0149 (7)	0.029 (2)*	0.239 (5)
C22'	0.6144 (8)	0.0833 (8)	0.0522 (7)	0.026 (3)*	0.239 (5)
H22'	0.7288	0.1111	0.0692	0.031*	0.239 (5)
C23'	0.4994 (12)	0.1506 (6)	0.0943 (6)	0.041 (3)*	0.239 (5)
H23'	0.5353	0.2245	0.1401	0.049*	0.239 (5)
C24'	0.3321 (11)	0.1099 (8)	0.0694 (7)	0.026 (3)*	0.239 (5)
H24'	0.2535	0.1560	0.0982	0.031*	0.239 (5)
C25'	0.2796 (8)	0.0019 (8)	0.0023 (6)	0.024 (2)*	0.239 (5)
H25'	0.1652	−0.0259	−0.0147	0.029*	0.239 (5)
C26'	0.3945 (11)	−0.0655 (6)	−0.0398 (5)	0.020 (2)*	0.239 (5)
H26'	0.3587	−0.1394	−0.0857	0.024*	0.239 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.01073 (15)	0.00465 (13)	0.00523 (13)	0.00414 (10)	0.00089 (10)	0.00079 (9)
N1	0.0142 (8)	0.0152 (7)	0.0120 (7)	0.0067 (6)	−0.0017 (6)	−0.0006 (6)
N2	0.0131 (8)	0.0146 (7)	0.0282 (9)	0.0054 (6)	0.0026 (6)	0.0016 (7)
N21	0.0107 (6)	0.0038 (5)	0.0037 (5)	0.0046 (5)	0.0003 (5)	0.0004 (4)
N22	0.0120 (7)	0.0041 (6)	0.0042 (6)	0.0043 (5)	0.0003 (5)	0.0006 (4)
C1	0.0116 (7)	0.0042 (6)	0.0054 (6)	0.0040 (5)	0.0007 (5)	0.0003 (5)
C2	0.0189 (9)	0.0070 (7)	0.0048 (7)	0.0055 (6)	0.0000 (6)	−0.0011 (5)
C3	0.0160 (8)	0.0075 (7)	0.0044 (6)	0.0051 (6)	−0.0002 (5)	0.0004 (5)
C4	0.0096 (7)	0.0058 (6)	0.0047 (6)	0.0036 (5)	0.0007 (5)	0.0015 (5)
C5	0.0087 (7)	0.0055 (6)	0.0049 (6)	0.0032 (5)	0.0005 (5)	0.0021 (5)
C6	0.0114 (7)	0.0060 (6)	0.0054 (6)	0.0046 (5)	0.0005 (5)	0.0020 (5)
C7	0.0201 (9)	0.0078 (7)	0.0080 (7)	0.0084 (6)	0.0004 (6)	0.0024 (6)
C8	0.0221 (9)	0.0071 (7)	0.0083 (7)	0.0092 (6)	0.0004 (6)	0.0014 (6)
C9	0.0132 (8)	0.0047 (6)	0.0070 (7)	0.0057 (5)	0.0008 (5)	0.0007 (5)
C10	0.0111 (7)	0.0040 (6)	0.0061 (6)	0.0042 (5)	0.0008 (5)	0.0001 (5)
C51	0.0091 (7)	0.0060 (6)	0.0068 (6)	0.0040 (5)	−0.0010 (5)	0.0001 (5)
C52	0.0098 (7)	0.0071 (7)	0.0069 (6)	0.0033 (5)	0.0014 (5)	0.0018 (5)
C53	0.0103 (7)	0.0043 (6)	0.0048 (6)	0.0037 (5)	0.0007 (5)	0.0011 (5)
C54	0.0091 (7)	0.0060 (6)	0.0073 (7)	0.0032 (5)	0.0012 (5)	0.0009 (5)
C55	0.0124 (8)	0.0083 (7)	0.0070 (7)	0.0037 (6)	0.0036 (6)	0.0016 (5)
C56	0.0150 (8)	0.0082 (7)	0.0054 (6)	0.0044 (6)	0.0008 (6)	0.0014 (5)
C57	0.0137 (8)	0.0090 (7)	0.0069 (7)	0.0045 (6)	−0.0007 (6)	−0.0002 (5)
C101	0.0098 (7)	0.0058 (6)	0.0101 (7)	0.0042 (5)	0.0014 (6)	0.0010 (5)
C102	0.0109 (7)	0.0048 (6)	0.0082 (7)	0.0030 (5)	0.0000 (5)	−0.0002 (5)
C103	0.0126 (8)	0.0039 (6)	0.0057 (6)	0.0042 (5)	0.0009 (5)	−0.0002 (5)
C104	0.0100 (7)	0.0063 (7)	0.0106 (7)	0.0039 (6)	0.0013 (6)	0.0004 (5)
C105	0.0108 (8)	0.0062 (7)	0.0123 (7)	0.0018 (6)	0.0003 (6)	−0.0008 (6)
C106	0.0127 (8)	0.0049 (6)	0.0114 (7)	0.0038 (6)	0.0021 (6)	−0.0004 (5)
C107	0.0131 (8)	0.0076 (7)	0.0152 (8)	0.0028 (6)	0.0009 (6)	0.0001 (6)
O1	0.0328 (10)	0.0391 (11)	0.0457 (12)	0.0103 (8)	−0.0022 (9)	0.0180 (9)
O2	0.0235 (8)	0.0377 (10)	0.0225 (8)	0.0011 (7)	0.0044 (6)	0.0088 (7)
N3	0.0139 (8)	0.0305 (10)	0.0277 (9)	−0.0015 (7)	0.0028 (7)	0.0122 (8)
C11	0.0135 (9)	0.0290 (11)	0.0193 (9)	−0.0047 (8)	0.0001 (7)	0.0104 (8)
C12	0.0147 (9)	0.0417 (13)	0.0239 (10)	−0.0056 (9)	−0.0021 (8)	0.0186 (10)
C13	0.0200 (10)	0.0498 (15)	0.0168 (10)	−0.0131 (10)	−0.0024 (8)	0.0113 (10)
C14	0.0297 (12)	0.0363 (13)	0.0199 (10)	−0.0125 (10)	0.0039 (9)	0.0030 (9)
C15	0.0359 (13)	0.0262 (11)	0.0236 (11)	−0.0056 (9)	0.0041 (9)	0.0098 (9)
C16	0.0242 (11)	0.0280 (11)	0.0176 (9)	−0.0040 (8)	0.0006 (8)	0.0109 (8)

Geometric parameters (Å, º)

Cu1—N21^i	1.9977 (17)	C105—C106	1.390 (3)
Cu1—N21	1.9977 (17)	C105—H105	0.9500
Cu1—N22^i	2.021 (2)	C106—H106	0.9500
Cu1—N22	2.021 (2)	O1—N3	1.229 (3)
N1—C57	1.150 (3)	O2—N3	1.226 (3)
N2—C107	1.153 (3)	N3—C11	1.474 (3)
N21—C1	1.381 (2)	C11—C16	1.385 (3)
N21—C4	1.381 (2)	C11—C12	1.394 (3)
N22—C6	1.381 (2)	C12—C13	1.387 (4)
N22—C9	1.382 (2)	C12—H12	0.9500
C1—C10^i	1.394 (2)	C13—C14	1.389 (4)
C1—C2	1.444 (2)	C13—H13	0.9500
C2—C3	1.358 (2)	C14—C15	1.396 (3)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.442 (2)	C15—C16	1.384 (4)
C3—H3	0.9500	C15—H15	0.9500
C4—C5	1.400 (2)	C16—H16	0.9500
C5—C6	1.397 (2)	O3—N4	1.212 (11)
C5—C53	1.495 (2)	O4—N4	1.188 (11)
C6—C7	1.443 (2)	N4—C21	1.489 (9)
C7—C8	1.360 (2)	C21—C22	1.3900
C7—H7	0.9500	C21—C26	1.3900
C8—C9	1.441 (2)	C22—C23	1.3900
C8—H8	0.9500	C22—H22	0.9500
C9—C10	1.397 (2)	C23—C24	1.3900
C10—C1^i	1.394 (2)	C23—H23	0.9500
C10—C103	1.495 (2)	C24—C25	1.3900
C51—C52	1.400 (2)	C24—H24	0.9500
C51—C56	1.402 (3)	C25—C26	1.3900
C51—C57	1.442 (3)	C25—H25	0.9500
C52—C53	1.391 (2)	C26—H26	0.9500
C52—H52	0.9500	O3'—N4'	1.242 (13)
C53—C54	1.407 (3)	O4'—N4'	1.207 (14)
C54—C55	1.395 (2)	N4'—C21'	1.481 (11)
C54—H54	0.9500	C21'—C22'	1.3900
C55—C56	1.387 (3)	C21'—C26'	1.3900
C55—H55	0.9500	C22'—C23'	1.3900
C56—H56	0.9500	C22'—H22'	0.9500
C101—C102	1.400 (2)	C23'—C24'	1.3900
C101—C106	1.402 (3)	C23'—H23'	0.9500
C101—C107	1.444 (3)	C24'—C25'	1.3900
C102—C103	1.393 (2)	C24'—H24'	0.9500
C102—H102	0.9500	C25'—C26'	1.3900
C103—C104	1.404 (3)	C25'—H25'	0.9500
C104—C105	1.394 (2)	C26'—H26'	0.9500
C104—H104	0.9500
N21—Cu1—N21^i	180.0	C103—C104—H104	119.5
N21^i—Cu1—N22^i	89.84 (8)	C106—C105—C104	120.29 (18)
N21—Cu1—N22^i	90.16 (8)	C106—C105—H105	119.9
N21^i—Cu1—N22	90.16 (8)	C104—C105—H105	119.9
N21—Cu1—N22	89.84 (8)	C105—C106—C101	118.74 (16)
N22—Cu1—N22^i	180.0	C105—C106—H106	120.6
C1—N21—C4	105.46 (14)	C101—C106—H106	120.6
C1—N21—Cu1	127.15 (11)	N2—C107—C101	178.9 (2)
C4—N21—Cu1	127.35 (12)	O2—N3—O1	123.8 (2)
C6—N22—C9	105.52 (14)	O2—N3—C11	117.9 (2)
C6—N22—Cu1	127.29 (11)	O1—N3—C11	118.4 (2)
C9—N22—Cu1	126.86 (12)	C16—C11—C12	122.6 (2)
N21—C1—C10^i	126.02 (15)	C16—C11—N3	119.0 (2)
N21—C1—C2	110.28 (14)	C12—C11—N3	118.5 (2)
C10^i—C1—C2	123.70 (15)	C13—C12—C11	118.1 (2)
C3—C2—C1	106.98 (15)	C13—C12—H12	121.0
C3—C2—H2	126.5	C11—C12—H12	121.0
C1—C2—H2	126.5	C12—C13—C14	120.5 (2)
C2—C3—C4	106.81 (15)	C12—C13—H13	119.8
C2—C3—H3	126.6	C14—C13—H13	119.8
C4—C3—H3	126.6	C13—C14—C15	120.1 (2)
N21—C4—C5	126.06 (15)	C13—C14—H14	120.0
N21—C4—C3	110.45 (15)	C15—C14—H14	120.0
C5—C4—C3	123.49 (15)	C16—C15—C14	120.4 (2)
C6—C5—C4	123.85 (15)	C16—C15—H15	119.8
C6—C5—C53	118.75 (15)	C14—C15—H15	119.8
C4—C5—C53	117.36 (14)	C15—C16—C11	118.4 (2)
N22—C6—C5	125.38 (15)	C15—C16—H16	120.8
N22—C6—C7	110.42 (14)	C11—C16—H16	120.8
C5—C6—C7	124.18 (15)	O4—N4—O3	126.3 (11)
C8—C7—C6	106.68 (15)	O4—N4—C21	117.8 (8)
C8—C7—H7	126.7	O3—N4—C21	115.9 (9)
C6—C7—H7	126.7	C22—C21—C26	120.0
C7—C8—C9	107.17 (16)	C22—C21—N4	119.6 (6)
C7—C8—H8	126.4	C26—C21—N4	120.3 (6)
C9—C8—H8	126.4	C23—C22—C21	120.0
N22—C9—C10	125.42 (15)	C23—C22—H22	120.0
N22—C9—C8	110.20 (15)	C21—C22—H22	120.0
C10—C9—C8	124.30 (15)	C22—C23—C24	120.0
C1^i—C10—C9	124.28 (15)	C22—C23—H23	120.0
C1^i—C10—C103	117.53 (15)	C24—C23—H23	120.0
C9—C10—C103	118.16 (15)	C25—C24—C23	120.0
C52—C51—C56	120.95 (16)	C25—C24—H24	120.0
C52—C51—C57	118.88 (17)	C23—C24—H24	120.0
C56—C51—C57	120.17 (16)	C26—C25—C24	120.0
C53—C52—C51	120.19 (17)	C26—C25—H25	120.0
C53—C52—H52	119.9	C24—C25—H25	120.0
C51—C52—H52	119.9	C25—C26—C21	120.0
C52—C53—C54	118.77 (16)	C25—C26—H26	120.0
C52—C53—C5	121.07 (16)	C21—C26—H26	120.0
C54—C53—C5	120.16 (15)	O4'—N4'—O3'	126.6 (14)
C55—C54—C53	120.69 (16)	O4'—N4'—C21'	114.6 (12)
C55—C54—H54	119.7	O3'—N4'—C21'	118.8 (13)
C53—C54—H54	119.7	C22'—C21'—C26'	120.0
C56—C55—C54	120.64 (17)	C22'—C21'—N4'	119.3 (8)
C56—C55—H55	119.7	C26'—C21'—N4'	120.7 (8)
C54—C55—H55	119.7	C21'—C22'—C23'	120.0
C55—C56—C51	118.75 (16)	C21'—C22'—H22'	120.0
C55—C56—H56	120.6	C23'—C22'—H22'	120.0
C51—C56—H56	120.6	C22'—C23'—C24'	120.0
N1—C57—C51	179.5 (2)	C22'—C23'—H23'	120.0
C102—C101—C106	121.22 (17)	C24'—C23'—H23'	120.0
C102—C101—C107	119.30 (18)	C23'—C24'—C25'	120.0
C106—C101—C107	119.48 (16)	C23'—C24'—H24'	120.0
C103—C102—C101	119.80 (18)	C25'—C24'—H24'	120.0
C103—C102—H102	120.1	C26'—C25'—C24'	120.0
C101—C102—H102	120.1	C26'—C25'—H25'	120.0
C102—C103—C104	118.85 (16)	C24'—C25'—H25'	120.0
C102—C103—C10	121.02 (17)	C25'—C26'—C21'	120.0
C104—C103—C10	120.12 (16)	C25'—C26'—H26'	120.0
C105—C104—C103	121.07 (17)	C21'—C26'—H26'	120.0
C105—C104—H104	119.5

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
C3—H3···N1^ii	0.95	2.54	3.463 (4)	164
C7—H7···N2^iii	0.95	2.73	3.608 (4)	155
C55—H55···N1^iv	0.95	2.83	3.477 (3)	126
C104—H104···N2^iv	0.95	2.62	3.316 (3)	130
C105—H105···N2^iv	0.95	2.95	3.475 (3)	116
C106—H106···N1^iii	0.95	2.51	3.405 (3)	157

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