Crystal structure of (pyridin-2-yl-methyl-idene)(tri-phenyl-meth-yl)amine.

The title Schiff base compound, C25H20N2, crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. In both mol-ecules, the imine group is approximately coplanar with the pyridine ring, with N-C-C-N torsion angles of 170.1 (3) and -172.0 (3) Å. In the crystal, A and B dimers are linked by pairs of C-H⋯π inter-actions and further C-H⋯π bonds link the dimers into a three-dimensional network.

Related literature

For the use of the pyridin-2-ylmethanimine Schiff base ligands for the development of a new generation of memory devices, multifunctional materials, and other magnetic applications, see: Capes et al. (2000 ▶); Guionneau et al. (2001 ▶); Létard et al. (1997 ▶, 1998 ▶); Liu et al. (2010 ▶); Murray (2008 ▶); Goodwin (2004 ▶); Gupta & Sutar (2008 ▶). For van der Waals radii, see: Bondi (1964 ▶)

Experimental

Crystal data

C25H20N2

M = 348.43

Orthorhombic,

a = 7.0719 (5) Å

b = 16.3972 (8) Å

c = 31.880 (2) Å

V = 3696.7 (4) Å3

Z = 8

Cu Kα radiation

μ = 0.56 mm−1

T = 173 K

0.30 × 0.26 × 0.22 mm

Data collection

Agilent Xcalibur (Sapphire3, Gemini ultra) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶) T min = 0.849, T max = 0.886

21735 measured reflections

6965 independent reflections

5059 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.153

S = 1.00

6965 reflections

487 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681401959X/tk5243sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681401959X/tk5243Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681401959X/tk5243Isup3.cdx

Click here for additional data file.

Supporting information file. DOI: 10.1107/S160053681401959X/tk5243Isup4.cml

Click here for additional data file.

A B A B . DOI: 10.1107/S160053681401959X/tk5243fig1.tif

A view of the two symmetry-independent mol­ecules (A and B) in (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Covalent bonds in A and B mol­ecules are shaded differently. The labeling scheme, 1–8, applied to the aromatic rings are used to identify the rings in the subsequent discussion.

Click here for additional data file.

ef y y x y z x y z . DOI: 10.1107/S160053681401959X/tk5243fig2.tif

A packing diagram for (I), displaying the inter­molecular ef C—H⋯π inter­actions (dashed lines). For clarity, only H atoms involved in C—H⋯π hydrogen bonding have been included. [Symmetry codes: (i) 1–x,  + y, 3/2–z; (ii) –x, y–1/2, 3/2–z; (iii) 1 + x, y, z; (iv) x–1, y, z].

CCDC reference: 1021733

Additional supporting information: crystallographic information; 3D view; checkCIF report

C25H20N2	F(000) = 1472
Mr = 348.43	Dx = 1.252 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3448 reflections
a = 7.0719 (5) Å	µ = 0.56 mm−1
b = 16.3972 (8) Å	T = 173 K
c = 31.880 (2) Å	Block, yellow
V = 3696.7 (4) Å3	0.30 × 0.26 × 0.22 mm
Z = 8

Agilent Xcalibur (Sapphire3, Gemini ultra) diffractometer	6965 independent reflections
Radiation source: fine-focus sealed tube	5059 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.058
Detector resolution: 8 pixels mm-1	θmax = 73.1°, θmin = 9.8°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −19→15
Tmin = 0.849, Tmax = 0.886	l = −28→39
21735 measured reflections

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)] = 0.057	H-atom parameters constrained
wR(F2) = 0.153	w = 1/[σ2(Fo2) + (0.0771P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
6965 reflections	Δρmax = 0.36 e Å−3
487 parameters	Δρmin = −0.18 e Å−3
0 restraints	Absolute structure: Flack (1983), XXX Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.3 (8)

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
N1	0.3234 (4)	0.72675 (16)	0.72533 (8)	0.0395 (6)
N2	0.0763 (4)	0.67303 (16)	0.63297 (8)	0.0368 (6)
C1	0.4649 (5)	0.7751 (2)	0.73827 (11)	0.0408 (7)
H1	0.4933	0.7761	0.7674	0.049*
C2	0.5717 (5)	0.8232 (2)	0.71190 (11)	0.0419 (8)
H2	0.6713	0.8561	0.7226	0.050*
C3	0.5300 (5)	0.8225 (2)	0.66932 (10)	0.0419 (8)
H3	0.5988	0.8559	0.6504	0.050*
C4	0.3861 (5)	0.77209 (19)	0.65489 (10)	0.0385 (7)
H4	0.3559	0.7696	0.6259	0.046*
C5	0.2876 (4)	0.72545 (18)	0.68395 (9)	0.0339 (7)
C6	0.1354 (5)	0.66888 (19)	0.67048 (10)	0.0359 (7)
H6	0.0833	0.6304	0.6895	0.043*
C7	−0.0641 (4)	0.61515 (18)	0.61548 (9)	0.0335 (7)
C8	−0.2019 (5)	0.66622 (19)	0.58873 (9)	0.0355 (7)
C13	−0.1588 (5)	0.7448 (2)	0.57610 (11)	0.0465 (8)
H13	−0.0432	0.7689	0.5848	0.056*
C12	−0.2826 (6)	0.7891 (2)	0.55077 (12)	0.0560 (10)
H12	−0.2515	0.8432	0.5425	0.067*
C11	−0.4510 (6)	0.7541 (2)	0.53771 (11)	0.0510 (9)
H11	−0.5344	0.7835	0.5199	0.061*
C10	−0.4964 (5)	0.6768 (2)	0.55064 (11)	0.0470 (9)
H10	−0.6125	0.6529	0.5421	0.056*
C9	−0.3737 (5)	0.6334 (2)	0.57618 (11)	0.0432 (8)
H9	−0.4079	0.5802	0.5852	0.052*
C14	0.0542 (4)	0.55700 (18)	0.58757 (9)	0.0338 (7)
C15	0.0086 (5)	0.5395 (2)	0.54651 (10)	0.0426 (8)
H15	−0.0942	0.5670	0.5335	0.051*
C16	0.1108 (6)	0.4824 (2)	0.52396 (11)	0.0491 (9)
H16	0.0777	0.4712	0.4957	0.059*
C17	0.2588 (5)	0.4419 (2)	0.54197 (11)	0.0475 (9)
H17	0.3262	0.4019	0.5265	0.057*
C18	0.3102 (5)	0.4593 (2)	0.58270 (10)	0.0421 (8)
H18	0.4148	0.4322	0.5952	0.051*
C19	0.2088 (5)	0.51641 (19)	0.60531 (10)	0.0390 (7)
H19	0.2447	0.5283	0.6334	0.047*
C20	−0.1792 (4)	0.56558 (19)	0.64745 (9)	0.0330 (6)
C21	−0.2010 (5)	0.48179 (19)	0.64471 (10)	0.0373 (7)
H21	−0.1317	0.4526	0.6241	0.045*
C22	−0.3221 (5)	0.4391 (2)	0.67150 (10)	0.0403 (7)
H22	−0.3347	0.3817	0.6688	0.048*
C23	−0.4230 (5)	0.4802 (2)	0.70172 (10)	0.0407 (7)
H23	−0.5065	0.4516	0.7198	0.049*
C24	−0.4017 (5)	0.5638 (2)	0.70542 (10)	0.0418 (8)
H24	−0.4700	0.5925	0.7264	0.050*
C25	−0.2821 (5)	0.60567 (19)	0.67889 (10)	0.0374 (7)
H25	−0.2691	0.6630	0.6820	0.045*
N1'	0.1678 (4)	0.52217 (16)	0.76822 (8)	0.0386 (6)
C1'	0.0245 (5)	0.4739 (2)	0.75559 (11)	0.0412 (8)
H1'	−0.0053	0.4722	0.7266	0.049*
N2'	0.4146 (4)	0.57659 (16)	0.86033 (8)	0.0363 (6)
C2'	−0.0814 (5)	0.4267 (2)	0.78293 (11)	0.0447 (8)
H2'	−0.1825	0.3941	0.7728	0.054*
C3'	−0.0381 (5)	0.4277 (2)	0.82482 (11)	0.0453 (8)
H3'	−0.1075	0.3952	0.8441	0.054*
C4'	0.1078 (5)	0.4768 (2)	0.83851 (10)	0.0389 (7)
H4'	0.1404	0.4789	0.8674	0.047*
C5'	0.2058 (4)	0.52291 (18)	0.80935 (9)	0.0335 (6)
C6'	0.3573 (4)	0.58008 (19)	0.82251 (9)	0.0348 (7)
H6'	0.4100	0.6181	0.8033	0.042*
C7'	0.5550 (4)	0.63331 (18)	0.87805 (9)	0.0315 (6)
C8'	0.6910 (5)	0.58111 (19)	0.90443 (9)	0.0333 (6)
C9'	0.8659 (5)	0.6119 (2)	0.91612 (10)	0.0400 (7)
H9'	0.9025	0.6647	0.9069	0.048*
C10'	0.9893 (5)	0.5664 (2)	0.94125 (10)	0.0448 (8)
H10'	1.1085	0.5883	0.9490	0.054*
C11'	0.9380 (6)	0.4904 (2)	0.95454 (11)	0.0506 (9)
H11'	1.0206	0.4597	0.9720	0.061*
C12'	0.7658 (6)	0.4580 (2)	0.94262 (12)	0.0507 (9)
H12'	0.7315	0.4047	0.9515	0.061*
C13'	0.6430 (5)	0.5026 (2)	0.91780 (10)	0.0438 (8)
H13'	0.5251	0.4797	0.9098	0.053*
C14'	0.4373 (4)	0.69107 (18)	0.90604 (9)	0.0330 (7)
C15'	0.4871 (5)	0.7085 (2)	0.94706 (10)	0.0403 (8)
H15'	0.5904	0.6807	0.9596	0.048*
C16'	0.3873 (6)	0.7665 (2)	0.97014 (11)	0.0488 (9)
H16'	0.4250	0.7788	0.9980	0.059*
C17'	0.2338 (5)	0.8060 (2)	0.95266 (10)	0.0444 (8)
H17'	0.1664	0.8458	0.9683	0.053*
C18'	0.1797 (5)	0.7872 (2)	0.91230 (10)	0.0409 (8)
H18'	0.0728	0.8133	0.9003	0.049*
C19'	0.2796 (4)	0.73047 (19)	0.88923 (10)	0.0375 (7)
H19'	0.2404	0.7181	0.8615	0.045*
C20'	0.6711 (4)	0.68358 (18)	0.84642 (9)	0.0308 (6)
C21'	0.6930 (4)	0.76739 (19)	0.84992 (9)	0.0348 (7)
H21'	0.6231	0.7962	0.8706	0.042*
C22'	0.8149 (5)	0.8098 (2)	0.82383 (10)	0.0392 (7)
H22'	0.8284	0.8672	0.8268	0.047*
C23'	0.9176 (5)	0.7686 (2)	0.79330 (10)	0.0423 (8)
H23'	1.0034	0.7973	0.7758	0.051*
C24'	0.8937 (5)	0.68586 (19)	0.78877 (10)	0.0388 (7)
H24'	0.9604	0.6575	0.7674	0.047*
C25'	0.7734 (5)	0.64361 (19)	0.81508 (9)	0.0361 (7)
H25'	0.7599	0.5863	0.8118	0.043*

	U11	U22	U33	U12	U13	U23
N1	0.0380 (14)	0.0299 (15)	0.0505 (15)	−0.0005 (12)	−0.0043 (12)	−0.0053 (12)
N2	0.0331 (14)	0.0311 (14)	0.0461 (14)	−0.0026 (11)	−0.0023 (11)	−0.0050 (11)
C1	0.0409 (17)	0.0314 (19)	0.0502 (18)	0.0022 (15)	−0.0073 (15)	−0.0054 (15)
C2	0.0355 (17)	0.0300 (18)	0.060 (2)	−0.0027 (13)	−0.0094 (15)	−0.0092 (15)
C3	0.0403 (18)	0.0332 (18)	0.0521 (18)	−0.0052 (14)	−0.0007 (15)	−0.0021 (14)
C4	0.0396 (17)	0.0265 (17)	0.0495 (17)	0.0003 (14)	0.0015 (14)	−0.0030 (14)
C5	0.0333 (15)	0.0263 (16)	0.0420 (16)	0.0035 (12)	−0.0037 (13)	−0.0055 (13)
C6	0.0359 (16)	0.0253 (17)	0.0465 (17)	−0.0004 (13)	0.0014 (13)	−0.0039 (13)
C7	0.0322 (14)	0.0267 (16)	0.0415 (16)	−0.0058 (12)	−0.0007 (13)	−0.0021 (12)
C8	0.0372 (16)	0.0290 (17)	0.0401 (15)	−0.0018 (13)	0.0027 (13)	−0.0010 (13)
C13	0.049 (2)	0.037 (2)	0.0540 (19)	−0.0083 (16)	−0.0019 (16)	0.0041 (15)
C12	0.065 (3)	0.045 (2)	0.059 (2)	0.002 (2)	−0.006 (2)	0.0096 (17)
C11	0.056 (2)	0.043 (2)	0.053 (2)	0.0137 (17)	−0.0087 (17)	−0.0002 (16)
C10	0.0377 (18)	0.050 (2)	0.0531 (19)	0.0015 (16)	−0.0034 (15)	0.0010 (16)
C9	0.0402 (18)	0.0307 (18)	0.059 (2)	−0.0017 (14)	−0.0037 (15)	0.0065 (15)
C14	0.0317 (15)	0.0266 (16)	0.0431 (16)	−0.0042 (12)	0.0025 (13)	0.0002 (13)
C15	0.0359 (17)	0.047 (2)	0.0454 (18)	0.0007 (16)	−0.0005 (14)	−0.0005 (15)
C16	0.050 (2)	0.049 (2)	0.0481 (18)	0.0021 (18)	0.0021 (16)	−0.0076 (16)
C17	0.047 (2)	0.043 (2)	0.053 (2)	0.0017 (17)	0.0104 (16)	−0.0014 (16)
C18	0.0352 (17)	0.0341 (19)	0.0571 (19)	−0.0004 (14)	0.0041 (15)	0.0052 (14)
C19	0.0350 (16)	0.0318 (18)	0.0502 (17)	−0.0028 (13)	−0.0005 (14)	0.0003 (14)
C20	0.0318 (15)	0.0264 (16)	0.0408 (15)	0.0008 (12)	−0.0018 (12)	−0.0020 (12)
C21	0.0386 (17)	0.0269 (17)	0.0464 (17)	−0.0060 (14)	0.0037 (14)	−0.0038 (13)
C22	0.0430 (18)	0.0280 (17)	0.0499 (17)	−0.0053 (14)	0.0003 (15)	0.0005 (13)
C23	0.0346 (16)	0.040 (2)	0.0474 (17)	−0.0012 (14)	0.0032 (14)	0.0097 (14)
C24	0.0387 (17)	0.040 (2)	0.0473 (18)	0.0079 (15)	0.0038 (14)	0.0039 (14)
C25	0.0379 (16)	0.0262 (17)	0.0481 (17)	0.0054 (13)	0.0046 (14)	0.0021 (13)
N1'	0.0375 (14)	0.0302 (15)	0.0480 (14)	0.0020 (11)	−0.0039 (11)	−0.0060 (12)
C1'	0.0427 (17)	0.0289 (19)	0.0519 (18)	0.0064 (14)	−0.0076 (14)	−0.0104 (14)
N2'	0.0331 (13)	0.0301 (14)	0.0456 (14)	−0.0055 (11)	−0.0010 (11)	−0.0025 (11)
C2'	0.0357 (17)	0.0340 (18)	0.064 (2)	−0.0061 (14)	−0.0058 (16)	−0.0139 (16)
C3'	0.0401 (18)	0.0351 (19)	0.061 (2)	−0.0049 (14)	0.0048 (16)	−0.0064 (16)
C4'	0.0385 (17)	0.0319 (18)	0.0462 (17)	−0.0006 (14)	0.0031 (14)	−0.0048 (14)
C5'	0.0335 (15)	0.0243 (16)	0.0428 (15)	0.0037 (12)	−0.0029 (13)	−0.0049 (12)
C6'	0.0370 (16)	0.0239 (17)	0.0435 (17)	−0.0012 (12)	−0.0038 (13)	−0.0021 (13)
C7'	0.0290 (14)	0.0265 (16)	0.0388 (15)	−0.0028 (12)	−0.0010 (12)	−0.0025 (12)
C8'	0.0365 (15)	0.0267 (16)	0.0368 (15)	0.0007 (13)	0.0003 (12)	−0.0002 (12)
C9'	0.0385 (17)	0.0355 (19)	0.0459 (18)	−0.0047 (14)	−0.0047 (14)	0.0032 (14)
C10'	0.0358 (17)	0.050 (2)	0.0484 (18)	0.0008 (16)	−0.0064 (14)	0.0027 (16)
C11'	0.051 (2)	0.050 (2)	0.0513 (19)	0.0112 (18)	−0.0074 (17)	0.0075 (17)
C12'	0.060 (2)	0.030 (2)	0.063 (2)	0.0001 (17)	−0.0034 (19)	0.0102 (15)
C13'	0.046 (2)	0.0341 (19)	0.0510 (18)	−0.0077 (15)	−0.0027 (15)	0.0047 (14)
C14'	0.0325 (15)	0.0267 (16)	0.0398 (15)	−0.0073 (12)	0.0017 (12)	0.0016 (12)
C15'	0.0358 (17)	0.045 (2)	0.0399 (16)	0.0008 (15)	−0.0025 (13)	0.0014 (14)
C16'	0.050 (2)	0.047 (2)	0.0494 (19)	0.0037 (18)	0.0028 (16)	−0.0078 (16)
C17'	0.0445 (19)	0.038 (2)	0.0506 (19)	0.0042 (16)	0.0092 (15)	0.0007 (15)
C18'	0.0340 (16)	0.035 (2)	0.0533 (19)	0.0007 (14)	0.0028 (14)	0.0058 (14)
C19'	0.0332 (15)	0.0323 (18)	0.0469 (17)	−0.0017 (13)	−0.0008 (13)	0.0043 (14)
C20'	0.0259 (13)	0.0249 (16)	0.0416 (15)	−0.0033 (11)	−0.0026 (12)	−0.0005 (12)
C21'	0.0344 (16)	0.0277 (17)	0.0422 (16)	−0.0030 (13)	0.0005 (13)	−0.0034 (13)
C22'	0.0396 (17)	0.0289 (18)	0.0492 (17)	−0.0049 (14)	−0.0004 (15)	0.0030 (13)
C23'	0.0366 (17)	0.043 (2)	0.0472 (18)	0.0011 (15)	0.0050 (14)	0.0106 (15)
C24'	0.0386 (17)	0.0349 (19)	0.0430 (17)	0.0078 (14)	0.0067 (14)	0.0047 (14)
C25'	0.0387 (16)	0.0256 (16)	0.0440 (16)	0.0019 (13)	0.0019 (13)	−0.0004 (13)

N1—C1	1.341 (4)	N1'—C5'	1.339 (4)
N1—C5	1.344 (4)	N1'—C1'	1.347 (4)
N2—C6	1.268 (4)	C1'—C2'	1.385 (5)
N2—C7	1.483 (4)	C1'—H1'	0.9500
C1—C2	1.379 (5)	N2'—C6'	1.273 (4)
C1—H1	0.9500	N2'—C7'	1.473 (4)
C2—C3	1.389 (5)	C2'—C3'	1.370 (5)
C2—H2	0.9500	C2'—H2'	0.9500
C3—C4	1.389 (5)	C3'—C4'	1.379 (5)
C3—H3	0.9500	C3'—H3'	0.9500
C4—C5	1.388 (4)	C4'—C5'	1.384 (4)
C4—H4	0.9500	C4'—H4'	0.9500
C5—C6	1.485 (4)	C5'—C6'	1.484 (4)
C6—H6	0.9500	C6'—H6'	0.9500
C7—C20	1.537 (4)	C7'—C8'	1.538 (4)
C7—C8	1.542 (4)	C7'—C20'	1.539 (4)
C7—C14	1.550 (4)	C7'—C14'	1.545 (4)
C8—C13	1.384 (4)	C8'—C9'	1.387 (4)
C8—C9	1.388 (5)	C8'—C13'	1.397 (4)
C13—C12	1.395 (5)	C9'—C10'	1.400 (5)
C13—H13	0.9500	C9'—H9'	0.9500
C12—C11	1.386 (6)	C10'—C11'	1.366 (5)
C12—H12	0.9500	C10'—H10'	0.9500
C11—C10	1.371 (5)	C11'—C12'	1.381 (6)
C11—H11	0.9500	C11'—H11'	0.9500
C10—C9	1.387 (5)	C12'—C13'	1.384 (5)
C10—H10	0.9500	C12'—H12'	0.9500
C9—H9	0.9500	C13'—H13'	0.9500
C14—C15	1.378 (4)	C14'—C15'	1.384 (4)
C14—C19	1.399 (4)	C14'—C19'	1.396 (4)
C15—C16	1.385 (5)	C15'—C16'	1.393 (5)
C15—H15	0.9500	C15'—H15'	0.9500
C16—C17	1.366 (5)	C16'—C17'	1.382 (5)
C16—H16	0.9500	C16'—H16'	0.9500
C17—C18	1.378 (5)	C17'—C18'	1.378 (5)
C17—H17	0.9500	C17'—H17'	0.9500
C18—C19	1.383 (4)	C18'—C19'	1.380 (4)
C18—H18	0.9500	C18'—H18'	0.9500
C19—H19	0.9500	C19'—H19'	0.9500
C20—C21	1.385 (4)	C20'—C21'	1.388 (4)
C20—C25	1.402 (4)	C20'—C25'	1.397 (4)
C21—C22	1.397 (4)	C21'—C22'	1.385 (4)
C21—H21	0.9500	C21'—H21'	0.9500
C22—C23	1.375 (5)	C22'—C23'	1.390 (5)
C22—H22	0.9500	C22'—H22'	0.9500
C23—C24	1.383 (5)	C23'—C24'	1.375 (5)
C23—H23	0.9500	C23'—H23'	0.9500
C24—C25	1.379 (5)	C24'—C25'	1.381 (4)
C24—H24	0.9500	C24'—H24'	0.9500
C25—H25	0.9500	C25'—H25'	0.9500
C1—N1—C5	116.9 (3)	C5'—N1'—C1'	116.7 (3)
C6—N2—C7	122.8 (3)	N1'—C1'—C2'	123.2 (3)
N1—C1—C2	124.0 (3)	N1'—C1'—H1'	118.4
N1—C1—H1	118.0	C2'—C1'—H1'	118.4
C2—C1—H1	118.0	C6'—N2'—C7'	123.3 (3)
C1—C2—C3	118.4 (3)	C3'—C2'—C1'	119.1 (3)
C1—C2—H2	120.8	C3'—C2'—H2'	120.5
C3—C2—H2	120.8	C1'—C2'—H2'	120.5
C2—C3—C4	119.0 (3)	C2'—C3'—C4'	118.8 (3)
C2—C3—H3	120.5	C2'—C3'—H3'	120.6
C4—C3—H3	120.5	C4'—C3'—H3'	120.6
C5—C4—C3	118.3 (3)	C3'—C4'—C5'	118.7 (3)
C5—C4—H4	120.8	C3'—C4'—H4'	120.6
C3—C4—H4	120.8	C5'—C4'—H4'	120.6
N1—C5—C4	123.5 (3)	N1'—C5'—C4'	123.5 (3)
N1—C5—C6	115.5 (3)	N1'—C5'—C6'	115.3 (3)
C4—C5—C6	121.0 (3)	C4'—C5'—C6'	121.1 (3)
N2—C6—C5	118.6 (3)	N2'—C6'—C5'	118.0 (3)
N2—C6—H6	120.7	N2'—C6'—H6'	121.0
C5—C6—H6	120.7	C5'—C6'—H6'	121.0
N2—C7—C20	116.3 (2)	N2'—C7'—C8'	106.2 (2)
N2—C7—C8	106.5 (2)	N2'—C7'—C20'	116.5 (2)
C20—C7—C8	108.6 (3)	C8'—C7'—C20'	108.8 (2)
N2—C7—C14	104.4 (2)	N2'—C7'—C14'	104.2 (2)
C20—C7—C14	110.0 (3)	C8'—C7'—C14'	111.2 (2)
C8—C7—C14	111.0 (2)	C20'—C7'—C14'	109.7 (2)
C13—C8—C9	118.0 (3)	C9'—C8'—C13'	118.0 (3)
C13—C8—C7	121.9 (3)	C9'—C8'—C7'	120.1 (3)
C9—C8—C7	120.1 (3)	C13'—C8'—C7'	121.9 (3)
C8—C13—C12	121.0 (4)	C8'—C9'—C10'	121.0 (3)
C8—C13—H13	119.5	C8'—C9'—H9'	119.5
C12—C13—H13	119.5	C10'—C9'—H9'	119.5
C11—C12—C13	119.8 (4)	C11'—C10'—C9'	119.9 (3)
C11—C12—H12	120.1	C11'—C10'—H10'	120.1
C13—C12—H12	120.1	C9'—C10'—H10'	120.1
C10—C11—C12	119.6 (4)	C10'—C11'—C12'	120.0 (3)
C10—C11—H11	120.2	C10'—C11'—H11'	120.0
C12—C11—H11	120.2	C12'—C11'—H11'	120.0
C11—C10—C9	120.3 (4)	C11'—C12'—C13'	120.5 (4)
C11—C10—H10	119.8	C11'—C12'—H12'	119.8
C9—C10—H10	119.8	C13'—C12'—H12'	119.8
C10—C9—C8	121.2 (3)	C12'—C13'—C8'	120.6 (3)
C10—C9—H9	119.4	C12'—C13'—H13'	119.7
C8—C9—H9	119.4	C8'—C13'—H13'	119.7
C15—C14—C19	117.9 (3)	C15'—C14'—C19'	118.0 (3)
C15—C14—C7	123.1 (3)	C15'—C14'—C7'	122.4 (3)
C19—C14—C7	118.9 (3)	C19'—C14'—C7'	119.5 (3)
C14—C15—C16	120.8 (3)	C14'—C15'—C16'	120.7 (3)
C14—C15—H15	119.6	C14'—C15'—H15'	119.6
C16—C15—H15	119.6	C16'—C15'—H15'	119.6
C17—C16—C15	120.7 (3)	C17'—C16'—C15'	120.3 (3)
C17—C16—H16	119.7	C17'—C16'—H16'	119.8
C15—C16—H16	119.7	C15'—C16'—H16'	119.8
C16—C17—C18	119.9 (3)	C18'—C17'—C16'	119.3 (3)
C16—C17—H17	120.1	C18'—C17'—H17'	120.3
C18—C17—H17	120.1	C16'—C17'—H17'	120.3
C17—C18—C19	119.6 (3)	C17'—C18'—C19'	120.4 (3)
C17—C18—H18	120.2	C17'—C18'—H18'	119.8
C19—C18—H18	120.2	C19'—C18'—H18'	119.8
C18—C19—C14	121.1 (3)	C18'—C19'—C14'	121.1 (3)
C18—C19—H19	119.4	C18'—C19'—H19'	119.5
C14—C19—H19	119.4	C14'—C19'—H19'	119.5
C21—C20—C25	116.9 (3)	C21'—C20'—C25'	117.7 (3)
C21—C20—C7	122.8 (3)	C21'—C20'—C7'	122.5 (3)
C25—C20—C7	120.1 (3)	C25'—C20'—C7'	119.6 (3)
C20—C21—C22	121.7 (3)	C22'—C21'—C20'	121.3 (3)
C20—C21—H21	119.1	C22'—C21'—H21'	119.4
C22—C21—H21	119.1	C20'—C21'—H21'	119.4
C23—C22—C21	120.1 (3)	C21'—C22'—C23'	120.1 (3)
C23—C22—H22	120.0	C21'—C22'—H22'	120.0
C21—C22—H22	120.0	C23'—C22'—H22'	120.0
C22—C23—C24	119.2 (3)	C24'—C23'—C22'	119.3 (3)
C22—C23—H23	120.4	C24'—C23'—H23'	120.4
C24—C23—H23	120.4	C22'—C23'—H23'	120.4
C25—C24—C23	120.5 (3)	C23'—C24'—C25'	120.4 (3)
C25—C24—H24	119.7	C23'—C24'—H24'	119.8
C23—C24—H24	119.7	C25'—C24'—H24'	119.8
C24—C25—C20	121.5 (3)	C24'—C25'—C20'	121.2 (3)
C24—C25—H25	119.2	C24'—C25'—H25'	119.4
C20—C25—H25	119.2	C20'—C25'—H25'	119.4
C5—N1—C1—C2	0.9 (5)	C5'—N1'—C1'—C2'	0.1 (5)
N1—C1—C2—C3	0.5 (5)	N1'—C1'—C2'—C3'	−0.9 (5)
C1—C2—C3—C4	−1.5 (5)	C1'—C2'—C3'—C4'	1.0 (5)
C2—C3—C4—C5	1.1 (5)	C2'—C3'—C4'—C5'	−0.3 (5)
C1—N1—C5—C4	−1.3 (5)	C1'—N1'—C5'—C4'	0.7 (4)
C1—N1—C5—C6	177.6 (3)	C1'—N1'—C5'—C6'	−176.8 (3)
C3—C4—C5—N1	0.3 (5)	C3'—C4'—C5'—N1'	−0.6 (5)
C3—C4—C5—C6	−178.5 (3)	C3'—C4'—C5'—C6'	176.7 (3)
C7—N2—C6—C5	175.0 (3)	C7'—N2'—C6'—C5'	−175.9 (3)
N1—C5—C6—N2	170.1 (3)	N1'—C5'—C6'—N2'	−172.0 (3)
C4—C5—C6—N2	−10.9 (5)	C4'—C5'—C6'—N2'	10.5 (4)
C6—N2—C7—C20	17.4 (4)	C6'—N2'—C7'—C8'	−137.2 (3)
C6—N2—C7—C8	138.6 (3)	C6'—N2'—C7'—C20'	−15.8 (4)
C6—N2—C7—C14	−103.9 (3)	C6'—N2'—C7'—C14'	105.2 (3)
N2—C7—C8—C13	15.9 (4)	N2'—C7'—C8'—C9'	162.9 (3)
C20—C7—C8—C13	141.9 (3)	C20'—C7'—C8'—C9'	36.7 (4)
C14—C7—C8—C13	−97.1 (3)	C14'—C7'—C8'—C9'	−84.3 (3)
N2—C7—C8—C9	−164.9 (3)	N2'—C7'—C8'—C13'	−18.0 (4)
C20—C7—C8—C9	−38.9 (4)	C20'—C7'—C8'—C13'	−144.2 (3)
C14—C7—C8—C9	82.1 (4)	C14'—C7'—C8'—C13'	94.8 (3)
C9—C8—C13—C12	−1.3 (5)	C13'—C8'—C9'—C10'	−1.2 (5)
C7—C8—C13—C12	177.9 (3)	C7'—C8'—C9'—C10'	178.0 (3)
C8—C13—C12—C11	−0.4 (6)	C8'—C9'—C10'—C11'	0.1 (5)
C13—C12—C11—C10	1.5 (6)	C9'—C10'—C11'—C12'	1.1 (6)
C12—C11—C10—C9	−0.9 (6)	C10'—C11'—C12'—C13'	−1.1 (6)
C11—C10—C9—C8	−0.9 (5)	C11'—C12'—C13'—C8'	−0.1 (6)
C13—C8—C9—C10	2.0 (5)	C9'—C8'—C13'—C12'	1.2 (5)
C7—C8—C9—C10	−177.2 (3)	C7'—C8'—C13'—C12'	−178.0 (3)
N2—C7—C14—C15	−129.1 (3)	N2'—C7'—C14'—C15'	130.6 (3)
C20—C7—C14—C15	105.4 (3)	C8'—C7'—C14'—C15'	16.5 (4)
C8—C7—C14—C15	−14.8 (4)	C20'—C7'—C14'—C15'	−103.9 (3)
N2—C7—C14—C19	54.7 (4)	N2'—C7'—C14'—C19'	−52.4 (3)
C20—C7—C14—C19	−70.8 (3)	C8'—C7'—C14'—C19'	−166.5 (3)
C8—C7—C14—C19	169.0 (3)	C20'—C7'—C14'—C19'	73.0 (3)
C19—C14—C15—C16	1.2 (5)	C19'—C14'—C15'—C16'	−2.8 (5)
C7—C14—C15—C16	−175.0 (3)	C7'—C14'—C15'—C16'	174.2 (3)
C14—C15—C16—C17	0.2 (6)	C14'—C15'—C16'—C17'	1.6 (6)
C15—C16—C17—C18	−1.5 (6)	C15'—C16'—C17'—C18'	0.5 (6)
C16—C17—C18—C19	1.4 (5)	C16'—C17'—C18'—C19'	−1.2 (5)
C17—C18—C19—C14	0.1 (5)	C17'—C18'—C19'—C14'	−0.1 (5)
C15—C14—C19—C18	−1.4 (5)	C15'—C14'—C19'—C18'	2.1 (5)
C7—C14—C19—C18	175.1 (3)	C7'—C14'—C19'—C18'	−175.0 (3)
N2—C7—C20—C21	−130.8 (3)	N2'—C7'—C20'—C21'	130.7 (3)
C8—C7—C20—C21	109.1 (3)	C8'—C7'—C20'—C21'	−109.3 (3)
C14—C7—C20—C21	−12.5 (4)	C14'—C7'—C20'—C21'	12.6 (4)
N2—C7—C20—C25	55.1 (4)	N2'—C7'—C20'—C25'	−55.4 (4)
C8—C7—C20—C25	−64.9 (4)	C8'—C7'—C20'—C25'	64.6 (3)
C14—C7—C20—C25	173.4 (3)	C14'—C7'—C20'—C25'	−173.5 (3)
C25—C20—C21—C22	1.1 (5)	C25'—C20'—C21'—C22'	−1.3 (5)
C7—C20—C21—C22	−173.2 (3)	C7'—C20'—C21'—C22'	172.7 (3)
C20—C21—C22—C23	−0.3 (5)	C20'—C21'—C22'—C23'	0.3 (5)
C21—C22—C23—C24	−0.6 (5)	C21'—C22'—C23'—C24'	1.4 (5)
C22—C23—C24—C25	0.6 (5)	C22'—C23'—C24'—C25'	−2.0 (5)
C23—C24—C25—C20	0.2 (5)	C23'—C24'—C25'—C20'	0.9 (5)
C21—C20—C25—C24	−1.0 (5)	C21'—C20'—C25'—C24'	0.7 (5)
C7—C20—C25—C24	173.4 (3)	C7'—C20'—C25'—C24'	−173.5 (3)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1, C1–C5 ring, Cg2 of ring C8–C13, Cg3 of ring C14–C19, Cg4 of ring C20–C25, Cg5 of ring N1′, C1′–C5′, Cg6 of ring C8′–C13′, Cg7 of ring C14′–C19′ and Cg8 of ring C20′–C25′.

D—H⋯A	D—H	H⋯A	H⋯Plane	D⋯A	D—H⋯A
C1—H1⋯Cg8	0.95	2.819	2.786 (3)	3.573	137
C1′—H1′⋯Cg4	0.95	2.789	2.749 (3)	3.545	137
C2—H2⋯Cg5i	0.95	2.769	2.751 (3)	3.591	145
C2′—H2′⋯Cg1ii	0.95	2.789	2.717 (3)	3.555	138
C4—H4⋯Cg2iii	0.95	3.150	2.982 (3)	3.692	118
C4′—H4′⋯Cg6iv	0.95	3.169	2.942 (3)	3.687	116
C9—H9⋯Cg4	0.95	3.104	2.533 (4)	3.670	120
C9′—H9′⋯Cg8	0.95	3.061	2.526 (4)	3.642	121
C10—H10⋯Cg3iv	0.95	3.077	3.038 (4)	3.823	136
C10′—H10′⋯Cg7iii	0.95	3.133	3.067 (4)	3.871	136
C15—H15⋯Cg2	0.95	3.030	2.386 (4)	3.717	130
C15′—15′⋯Cg6	0.95	3.027	2.387 (4)	3.715	131
C21—H21⋯Cg3	0.95	2.897	2.424 (4)	3.614	133
C21′—H21′⋯Cg7	0.95	2.886	2.435 (4)	3.604	133
C25—H25⋯Cg1iv	0.95	2.859	2.824 (3)	3.493	125
C25′—H25′⋯Cg5iii	0.95	2.865	2.824 (3)	3.496	125

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