N,N'-Bis(4-chloro-benzyl-idene)-3,3'-dimeth-oxy-biphenyl-4,4'-diamine.

The title compound, C(28)H(22)Cl(2)N(2)O(2), crystallized with two independent mol-ecules (A and B) in the asymmetric unit. The two mol-ecules differ essentially in the orientation of the outer aromatic rings. These dihedral angles are 56.07 (13) and 27.62 (15) Å for mol-ecules A and B, respectively. In the crystal, A mol-ecules are related as centrosymmetric pairs through a weak π-π inter-action [centroid-centroid distance = 3.6959 (15) Å]. There are also a number of inter-molecular C-H⋯O, C-H⋯N and C-H⋯π inter-actions present.

Related literature

For early work on the synthesis of multidentate Schiff base ligands, see: Weber (1967 ▶); Lesser et al. (1975 ▶); Munro & Camp (2003 ▶). For examples of Schiff base metal complexes exhibiting biological properties, see: Golcu et al. (2005 ▶); Liu & Yang (2010 ▶). For examples of Schiff base metal complexes exhibiting catalytic properties, see: Daier et al. (2004 ▶). For details of photochromic properties of some Schiff base complexes, see: Zgierski & Grabowska (2000 ▶). For examples of some similar 4,4′-biphenyl diamine Schiff bases, see: Lesser et al. (1975 ▶); Aygun et al. (2004 ▶); Hou et al. (2006 ▶). For details of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C28H22Cl2N2O2

M = 489.38

Triclinic,

a = 9.2358 (5) Å

b = 11.8559 (6) Å

c = 23.5218 (12) Å

α = 75.810 (4)°

β = 80.326 (4)°

γ = 79.288 (4)°

V = 2433.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 173 K

0.45 × 0.18 × 0.12 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009 ▶) T min = 0.772, T max = 1.000

29251 measured reflections

9183 independent reflections

5705 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.125

S = 0.98

9183 reflections

617 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.30 e Å−3

Data collection: X-AREA (Stoe & Cie, 2009 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97, PLATON and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015467/fl2345sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015467/fl2345Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811015467/fl2345Isup3.cml

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

C28H22Cl2N2O2	Z = 4
Mr = 489.38	F(000) = 1016
Triclinic, P1	Dx = 1.336 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2358 (5) Å	Cell parameters from 16478 reflections
b = 11.8559 (6) Å	θ = 1.8–26.0°
c = 23.5218 (12) Å	µ = 0.30 mm−1
α = 75.810 (4)°	T = 173 K
β = 80.326 (4)°	Rod, brown
γ = 79.288 (4)°	0.45 × 0.18 × 0.12 mm
V = 2433.1 (2) Å3

Stoe IPDS 2 diffractometer	9183 independent reflections
Radiation source: fine-focus sealed tube	5705 reflections with I > 2σ(I)
graphite	Rint = 0.071
φ and ω scans	θmax = 25.6°, θmin = 1.8°
Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009)	h = −11→11
Tmin = 0.772, Tmax = 1.000	k = −14→14
29251 measured reflections	l = −28→28

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0607P)2] where P = (Fo2 + 2Fc2)/3
9183 reflections	(Δ/σ)max = 0.001
617 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

	x	y	z	Uiso*/Ueq
Cl1	−0.16693 (10)	0.73278 (7)	−0.42605 (3)	0.0557 (3)
Cl2	0.76750 (12)	0.00726 (7)	0.47655 (4)	0.0700 (3)
O1	0.1449 (2)	0.70175 (15)	−0.09211 (8)	0.0440 (7)
O2	0.2304 (2)	0.10960 (15)	0.19381 (8)	0.0423 (6)
N1	0.0777 (3)	0.57226 (18)	−0.15956 (9)	0.0379 (7)
N2	0.4364 (3)	0.19921 (19)	0.22848 (9)	0.0399 (8)
C1	−0.1290 (3)	0.6770 (2)	−0.35318 (11)	0.0402 (9)
C2	−0.2099 (4)	0.5962 (3)	−0.31557 (13)	0.0497 (11)
C3	−0.1785 (3)	0.5547 (3)	−0.25790 (13)	0.0478 (10)
C4	−0.0646 (3)	0.5919 (2)	−0.23855 (11)	0.0393 (9)
C5	0.0142 (3)	0.6737 (2)	−0.27775 (12)	0.0461 (10)
C6	−0.0169 (3)	0.7171 (2)	−0.33514 (12)	0.0473 (10)
C7	−0.0298 (3)	0.5443 (2)	−0.17770 (12)	0.0425 (9)
C8	0.1164 (3)	0.5157 (2)	−0.10280 (11)	0.0348 (8)
C9	0.1611 (3)	0.5830 (2)	−0.06896 (11)	0.0352 (8)
C10	0.2146 (3)	0.5283 (2)	−0.01568 (11)	0.0361 (9)
C11	0.2278 (3)	0.4060 (2)	0.00542 (11)	0.0352 (8)
C12	0.1835 (3)	0.3401 (2)	−0.02828 (11)	0.0395 (9)
C13	0.1285 (3)	0.3946 (2)	−0.08133 (11)	0.0398 (9)
C14	0.2887 (3)	0.3500 (2)	0.06174 (11)	0.0352 (8)
C15	0.4010 (3)	0.3933 (2)	0.07895 (12)	0.0447 (9)
C16	0.4541 (3)	0.3410 (2)	0.13245 (12)	0.0454 (10)
C17	0.3966 (3)	0.2461 (2)	0.17100 (11)	0.0378 (9)
C18	0.2828 (3)	0.2025 (2)	0.15388 (11)	0.0359 (8)
C19	0.2320 (3)	0.2536 (2)	0.09986 (11)	0.0359 (8)
C20	0.5723 (4)	0.1773 (2)	0.23557 (12)	0.0470 (10)
C21	0.6195 (3)	0.1368 (2)	0.29511 (12)	0.0409 (9)
C22	0.7661 (3)	0.0873 (3)	0.30185 (14)	0.0519 (11)
C23	0.8113 (4)	0.0469 (2)	0.35752 (15)	0.0529 (11)
C24	0.7101 (4)	0.0574 (2)	0.40639 (13)	0.0466 (10)
C25	0.5640 (3)	0.1055 (2)	0.40128 (12)	0.0449 (10)
C26	0.5199 (3)	0.1443 (2)	0.34562 (12)	0.0417 (9)
C27	0.1841 (4)	0.7738 (2)	−0.05816 (14)	0.0552 (10)
C28	0.1111 (3)	0.0658 (3)	0.17929 (13)	0.0509 (10)
Cl3	0.72546 (11)	0.22366 (9)	0.91179 (4)	0.0780 (4)
Cl4	−0.40375 (15)	0.99270 (9)	0.05465 (5)	0.1072 (5)
O3	0.4123 (2)	0.30306 (14)	0.58097 (8)	0.0405 (6)
O4	0.1571 (2)	0.91381 (15)	0.32380 (8)	0.0416 (6)
N3	0.4599 (3)	0.43315 (19)	0.65042 (9)	0.0392 (8)
N4	−0.0211 (3)	0.79885 (18)	0.28786 (9)	0.0371 (7)
C29	0.6336 (3)	0.2908 (3)	0.85004 (12)	0.0470 (10)
C30	0.5040 (3)	0.3671 (3)	0.85675 (12)	0.0533 (11)
C31	0.4329 (3)	0.4206 (3)	0.80728 (12)	0.0509 (10)
C32	0.4907 (3)	0.3992 (2)	0.75239 (11)	0.0373 (9)
C33	0.6227 (3)	0.3212 (2)	0.74676 (12)	0.0411 (9)
C34	0.6943 (3)	0.2663 (3)	0.79566 (13)	0.0490 (10)
C35	0.4114 (3)	0.4551 (2)	0.70078 (12)	0.0413 (9)
C36	0.3826 (3)	0.4902 (2)	0.60174 (10)	0.0338 (8)
C37	0.3332 (3)	0.6105 (2)	0.58768 (11)	0.0415 (9)
C38	0.2646 (3)	0.6615 (2)	0.53740 (11)	0.0410 (9)
C39	0.2441 (3)	0.5941 (2)	0.49943 (10)	0.0330 (8)
C40	0.2939 (3)	0.4727 (2)	0.51341 (10)	0.0331 (8)
C41	0.3628 (3)	0.4211 (2)	0.56359 (11)	0.0329 (8)
C42	0.1699 (3)	0.6476 (2)	0.44576 (10)	0.0324 (8)
C43	0.0753 (3)	0.5893 (2)	0.42723 (11)	0.0371 (8)
C44	0.0071 (3)	0.6402 (2)	0.37685 (11)	0.0363 (8)
C45	0.0340 (3)	0.7494 (2)	0.34255 (10)	0.0333 (8)
C46	0.1313 (3)	0.8083 (2)	0.36068 (11)	0.0332 (8)
C47	0.1964 (3)	0.7585 (2)	0.41185 (10)	0.0333 (8)
C48	−0.1580 (3)	0.7995 (2)	0.28454 (12)	0.0419 (9)
C49	−0.2182 (3)	0.8436 (2)	0.22789 (13)	0.0410 (9)
C50	−0.3700 (4)	0.8773 (3)	0.22698 (16)	0.0584 (12)
C51	−0.4283 (4)	0.9242 (3)	0.17360 (19)	0.0694 (14)
C52	−0.3328 (5)	0.9342 (3)	0.12174 (17)	0.0634 (13)
C53	−0.1824 (4)	0.8986 (3)	0.12114 (14)	0.0577 (13)
C54	−0.1256 (4)	0.8540 (2)	0.17442 (12)	0.0464 (10)
C55	0.3890 (4)	0.2297 (2)	0.54500 (13)	0.0507 (10)
C56	0.2591 (4)	0.9755 (2)	0.33901 (13)	0.0493 (10)
H2	−0.28600	0.56920	−0.32890	0.0600*
H3	−0.23530	0.50020	−0.23120	0.0570*
H5	0.09120	0.70050	−0.26490	0.0550*
H6	0.03760	0.77340	−0.36170	0.0570*
H7	−0.08930	0.49140	−0.15130	0.0510*
H10	0.24300	0.57480	0.00700	0.0430*
H12	0.19100	0.25710	−0.01490	0.0470*
H13	0.09830	0.34790	−0.10350	0.0480*
H15	0.44130	0.45910	0.05390	0.0540*
H16	0.53190	0.37090	0.14310	0.0540*
H19	0.15660	0.22220	0.08850	0.0430*
H20	0.64560	0.18710	0.20190	0.0570*
H22	0.83620	0.08100	0.26780	0.0620*
H23	0.91140	0.01230	0.36170	0.0630*
H25	0.49460	0.11180	0.43550	0.0540*
H26	0.41900	0.17690	0.34190	0.0500*
H27A	0.28880	0.74970	−0.05210	0.0830*
H27B	0.12170	0.76480	−0.01980	0.0830*
H27C	0.16880	0.85640	−0.07940	0.0830*
H28A	0.14360	0.03600	0.14310	0.0760*
H28B	0.02690	0.12930	0.17300	0.0760*
H28C	0.08070	0.00190	0.21180	0.0760*
H30	0.46380	0.38300	0.89440	0.0640*
H31	0.34250	0.47300	0.81140	0.0610*
H33	0.66370	0.30580	0.70910	0.0490*
H34	0.78360	0.21250	0.79200	0.0590*
H35	0.32230	0.50870	0.70540	0.0500*
H37	0.34660	0.65840	0.61280	0.0500*
H38	0.23110	0.74380	0.52870	0.0490*
H40	0.28020	0.42500	0.48820	0.0400*
H43	0.05700	0.51360	0.44940	0.0450*
H44	−0.05920	0.59960	0.36560	0.0440*
H47	0.25980	0.80010	0.42410	0.0400*
H48	−0.22170	0.77090	0.31920	0.0500*
H50	−0.43510	0.86850	0.26310	0.0700*
H51	−0.53210	0.94880	0.17320	0.0830*
H53	−0.11830	0.90450	0.08480	0.0690*
H54	−0.02160	0.83010	0.17440	0.0560*
H55A	0.43770	0.25550	0.50470	0.0760*
H55B	0.28220	0.23480	0.54430	0.0760*
H55C	0.43100	0.14810	0.56120	0.0760*
H56A	0.35490	0.92420	0.34290	0.0740*
H56B	0.21950	0.99830	0.37660	0.0740*
H56C	0.27280	1.04610	0.30790	0.0740*

	U11	U22	U33	U12	U13	U23
Cl1	0.0751 (6)	0.0561 (4)	0.0355 (4)	−0.0003 (4)	−0.0251 (4)	−0.0043 (3)
Cl2	0.1128 (8)	0.0452 (4)	0.0613 (5)	−0.0069 (4)	−0.0571 (5)	−0.0019 (4)
O1	0.0574 (13)	0.0350 (10)	0.0411 (11)	−0.0066 (9)	−0.0244 (10)	0.0007 (8)
O2	0.0463 (12)	0.0427 (10)	0.0345 (10)	−0.0121 (9)	−0.0138 (9)	0.0079 (8)
N1	0.0447 (14)	0.0417 (12)	0.0265 (11)	−0.0009 (10)	−0.0120 (10)	−0.0053 (9)
N2	0.0458 (15)	0.0419 (13)	0.0308 (12)	−0.0064 (11)	−0.0136 (10)	0.0001 (9)
C1	0.0523 (18)	0.0380 (15)	0.0290 (14)	0.0033 (13)	−0.0152 (13)	−0.0058 (11)
C2	0.056 (2)	0.0555 (18)	0.0438 (17)	−0.0151 (15)	−0.0209 (15)	−0.0079 (14)
C3	0.0536 (19)	0.0512 (17)	0.0400 (16)	−0.0161 (14)	−0.0134 (14)	−0.0018 (13)
C4	0.0450 (17)	0.0403 (15)	0.0322 (14)	−0.0010 (13)	−0.0106 (12)	−0.0074 (12)
C5	0.0530 (19)	0.0478 (16)	0.0387 (16)	−0.0128 (14)	−0.0154 (14)	−0.0015 (13)
C6	0.0537 (19)	0.0493 (17)	0.0371 (15)	−0.0098 (14)	−0.0142 (14)	0.0010 (13)
C7	0.0498 (19)	0.0425 (15)	0.0345 (15)	−0.0039 (13)	−0.0087 (13)	−0.0071 (12)
C8	0.0323 (15)	0.0419 (15)	0.0265 (13)	−0.0035 (11)	−0.0034 (11)	−0.0024 (11)
C9	0.0360 (16)	0.0360 (14)	0.0313 (14)	−0.0024 (11)	−0.0082 (12)	−0.0030 (11)
C10	0.0366 (16)	0.0421 (15)	0.0297 (14)	−0.0057 (12)	−0.0096 (12)	−0.0045 (11)
C11	0.0342 (15)	0.0410 (15)	0.0254 (13)	−0.0025 (12)	−0.0023 (11)	−0.0012 (11)
C12	0.0502 (18)	0.0356 (14)	0.0306 (14)	−0.0043 (12)	−0.0080 (13)	−0.0030 (11)
C13	0.0477 (18)	0.0420 (15)	0.0313 (14)	−0.0075 (13)	−0.0096 (13)	−0.0073 (12)
C14	0.0337 (15)	0.0418 (15)	0.0271 (13)	−0.0016 (12)	−0.0061 (11)	−0.0035 (11)
C15	0.0465 (18)	0.0499 (16)	0.0339 (15)	−0.0136 (14)	−0.0115 (13)	0.0068 (12)
C16	0.0463 (18)	0.0521 (17)	0.0379 (15)	−0.0154 (14)	−0.0150 (13)	0.0024 (13)
C17	0.0418 (17)	0.0409 (15)	0.0283 (13)	−0.0030 (13)	−0.0102 (12)	−0.0020 (11)
C18	0.0374 (16)	0.0362 (14)	0.0305 (14)	−0.0039 (12)	−0.0046 (12)	−0.0020 (11)
C19	0.0385 (16)	0.0404 (15)	0.0274 (13)	−0.0037 (12)	−0.0072 (12)	−0.0044 (11)
C20	0.053 (2)	0.0515 (17)	0.0338 (15)	−0.0104 (15)	−0.0049 (14)	−0.0029 (13)
C21	0.0422 (17)	0.0395 (15)	0.0409 (16)	−0.0059 (13)	−0.0133 (13)	−0.0034 (12)
C22	0.0463 (19)	0.0580 (18)	0.0496 (18)	−0.0049 (15)	−0.0097 (15)	−0.0082 (15)
C23	0.0469 (19)	0.0454 (17)	0.068 (2)	0.0007 (14)	−0.0264 (17)	−0.0087 (15)
C24	0.067 (2)	0.0296 (14)	0.0500 (18)	−0.0074 (14)	−0.0317 (16)	−0.0055 (12)
C25	0.060 (2)	0.0396 (15)	0.0369 (15)	−0.0075 (14)	−0.0129 (14)	−0.0074 (12)
C26	0.0441 (17)	0.0384 (15)	0.0421 (16)	−0.0027 (13)	−0.0133 (14)	−0.0056 (12)
C27	0.076 (2)	0.0361 (15)	0.0582 (19)	−0.0058 (15)	−0.0318 (17)	−0.0055 (14)
C28	0.0522 (19)	0.0506 (17)	0.0459 (17)	−0.0179 (15)	−0.0138 (15)	0.0093 (14)
Cl3	0.0771 (7)	0.1085 (7)	0.0427 (5)	0.0008 (5)	−0.0327 (4)	−0.0004 (4)
Cl4	0.1606 (12)	0.0747 (6)	0.1045 (8)	−0.0176 (7)	−0.1093 (9)	0.0083 (6)
O3	0.0538 (12)	0.0333 (9)	0.0357 (10)	−0.0049 (8)	−0.0204 (9)	−0.0017 (8)
O4	0.0491 (12)	0.0377 (10)	0.0373 (10)	−0.0147 (9)	−0.0171 (9)	0.0067 (8)
N3	0.0441 (14)	0.0452 (13)	0.0307 (12)	−0.0057 (11)	−0.0137 (10)	−0.0077 (10)
N4	0.0399 (14)	0.0415 (12)	0.0297 (12)	−0.0051 (10)	−0.0137 (10)	−0.0020 (9)
C29	0.0462 (19)	0.0621 (19)	0.0322 (15)	−0.0102 (15)	−0.0160 (13)	−0.0007 (13)
C30	0.053 (2)	0.078 (2)	0.0290 (15)	−0.0047 (17)	−0.0087 (14)	−0.0137 (14)
C31	0.0435 (18)	0.070 (2)	0.0372 (16)	0.0045 (15)	−0.0077 (13)	−0.0160 (14)
C32	0.0368 (16)	0.0468 (16)	0.0291 (14)	−0.0058 (13)	−0.0075 (12)	−0.0080 (11)
C33	0.0407 (17)	0.0527 (16)	0.0313 (14)	−0.0064 (13)	−0.0069 (12)	−0.0107 (12)
C34	0.0433 (18)	0.0587 (18)	0.0442 (17)	−0.0001 (14)	−0.0134 (14)	−0.0102 (14)
C35	0.0384 (16)	0.0477 (16)	0.0358 (15)	−0.0021 (13)	−0.0077 (12)	−0.0066 (12)
C36	0.0362 (15)	0.0407 (14)	0.0251 (13)	−0.0085 (12)	−0.0086 (11)	−0.0033 (11)
C37	0.0567 (19)	0.0382 (15)	0.0330 (14)	−0.0079 (13)	−0.0136 (13)	−0.0087 (11)
C38	0.0583 (19)	0.0315 (13)	0.0331 (14)	−0.0056 (13)	−0.0140 (13)	−0.0026 (11)
C39	0.0347 (15)	0.0357 (14)	0.0275 (13)	−0.0070 (11)	−0.0066 (11)	−0.0018 (11)
C40	0.0367 (15)	0.0358 (14)	0.0280 (13)	−0.0096 (11)	−0.0082 (11)	−0.0035 (11)
C41	0.0357 (15)	0.0314 (13)	0.0304 (13)	−0.0061 (11)	−0.0080 (11)	−0.0011 (10)
C42	0.0327 (15)	0.0369 (14)	0.0265 (13)	−0.0039 (11)	−0.0049 (11)	−0.0055 (11)
C43	0.0419 (16)	0.0361 (14)	0.0324 (14)	−0.0082 (12)	−0.0089 (12)	−0.0013 (11)
C44	0.0347 (15)	0.0431 (15)	0.0324 (14)	−0.0119 (12)	−0.0095 (12)	−0.0026 (11)
C45	0.0298 (15)	0.0396 (14)	0.0289 (13)	−0.0028 (11)	−0.0071 (11)	−0.0044 (11)
C46	0.0328 (15)	0.0361 (14)	0.0287 (13)	−0.0053 (11)	−0.0041 (11)	−0.0030 (11)
C47	0.0341 (15)	0.0365 (14)	0.0299 (13)	−0.0067 (11)	−0.0077 (11)	−0.0052 (11)
C48	0.0429 (18)	0.0457 (16)	0.0367 (15)	−0.0068 (13)	−0.0102 (13)	−0.0050 (12)
C49	0.0414 (17)	0.0377 (15)	0.0481 (17)	−0.0052 (12)	−0.0200 (14)	−0.0085 (12)
C50	0.047 (2)	0.062 (2)	0.073 (2)	−0.0036 (16)	−0.0259 (17)	−0.0189 (17)
C51	0.060 (2)	0.057 (2)	0.102 (3)	0.0044 (17)	−0.052 (2)	−0.020 (2)
C52	0.090 (3)	0.0412 (17)	0.072 (2)	−0.0083 (17)	−0.060 (2)	−0.0046 (16)
C53	0.084 (3)	0.0481 (17)	0.0472 (18)	−0.0153 (17)	−0.0320 (18)	−0.0025 (14)
C54	0.0548 (19)	0.0441 (16)	0.0435 (17)	−0.0075 (14)	−0.0236 (15)	−0.0042 (13)
C55	0.074 (2)	0.0327 (15)	0.0489 (17)	−0.0053 (14)	−0.0258 (16)	−0.0059 (13)
C56	0.060 (2)	0.0463 (16)	0.0423 (16)	−0.0218 (15)	−0.0163 (14)	0.0056 (13)

Cl1—C1	1.749 (3)	C22—H22	0.9500
Cl2—C24	1.748 (3)	C23—H23	0.9500
Cl3—C29	1.749 (3)	C25—H25	0.9500
Cl4—C52	1.744 (4)	C26—H26	0.9500
O1—C9	1.369 (3)	C27—H27C	0.9800
O1—C27	1.430 (3)	C27—H27B	0.9800
O2—C28	1.424 (4)	C27—H27A	0.9800
O2—C18	1.367 (3)	C28—H28A	0.9800
O3—C41	1.371 (3)	C28—H28B	0.9800
O3—C55	1.418 (3)	C28—H28C	0.9800
O4—C46	1.372 (3)	C29—C30	1.371 (5)
O4—C56	1.431 (4)	C29—C34	1.384 (4)
N1—C7	1.270 (4)	C30—C31	1.388 (4)
N1—C8	1.412 (3)	C31—C32	1.377 (4)
N2—C17	1.412 (3)	C32—C33	1.395 (4)
N2—C20	1.264 (5)	C32—C35	1.474 (4)
N3—C35	1.265 (3)	C33—C34	1.383 (4)
N3—C36	1.412 (3)	C36—C37	1.389 (3)
N4—C45	1.413 (3)	C36—C41	1.408 (3)
N4—C48	1.278 (4)	C37—C38	1.387 (4)
C1—C2	1.374 (4)	C38—C39	1.391 (3)
C1—C6	1.381 (4)	C39—C40	1.401 (3)
C2—C3	1.385 (4)	C39—C42	1.484 (3)
C3—C4	1.393 (4)	C40—C41	1.388 (4)
C4—C7	1.470 (4)	C42—C43	1.390 (4)
C4—C5	1.385 (4)	C42—C47	1.402 (3)
C5—C6	1.380 (4)	C43—C44	1.387 (4)
C8—C9	1.409 (4)	C44—C45	1.389 (3)
C8—C13	1.390 (3)	C45—C46	1.409 (4)
C9—C10	1.388 (4)	C46—C47	1.386 (4)
C10—C11	1.402 (3)	C48—C49	1.469 (4)
C11—C14	1.481 (4)	C49—C50	1.387 (5)
C11—C12	1.392 (4)	C49—C54	1.389 (4)
C12—C13	1.389 (4)	C50—C51	1.396 (6)
C14—C15	1.394 (4)	C51—C52	1.374 (6)
C14—C19	1.395 (4)	C52—C53	1.373 (6)
C15—C16	1.386 (4)	C53—C54	1.385 (4)
C16—C17	1.389 (4)	C30—H30	0.9500
C17—C18	1.407 (4)	C31—H31	0.9500
C18—C19	1.385 (4)	C33—H33	0.9500
C20—C21	1.476 (4)	C34—H34	0.9500
C21—C22	1.391 (4)	C35—H35	0.9500
C21—C26	1.386 (4)	C37—H37	0.9500
C22—C23	1.386 (5)	C38—H38	0.9500
C23—C24	1.370 (5)	C40—H40	0.9500
C24—C25	1.377 (5)	C43—H43	0.9500
C25—C26	1.381 (4)	C44—H44	0.9500
C2—H2	0.9500	C47—H47	0.9500
C3—H3	0.9500	C48—H48	0.9500
C5—H5	0.9500	C50—H50	0.9500
C6—H6	0.9500	C51—H51	0.9500
C7—H7	0.9500	C53—H53	0.9500
C10—H10	0.9500	C54—H54	0.9500
C12—H12	0.9500	C55—H55A	0.9800
C13—H13	0.9500	C55—H55B	0.9800
C15—H15	0.9500	C55—H55C	0.9800
C16—H16	0.9500	C56—H56A	0.9800
C19—H19	0.9500	C56—H56B	0.9800
C20—H20	0.9500	C56—H56C	0.9800
Cl1···Cl2i	3.5048 (12)	Cl4···Cl4ii	3.3173 (18)
C9—O1—C27	117.1 (2)	H28A—C28—H28B	110.00
C18—O2—C28	117.0 (2)	O2—C28—H28A	109.00
C41—O3—C55	116.9 (2)	O2—C28—H28B	109.00
C46—O4—C56	117.7 (2)	O2—C28—H28C	109.00
C7—N1—C8	119.7 (2)	Cl3—C29—C30	119.1 (2)
C17—N2—C20	119.2 (2)	Cl3—C29—C34	119.2 (2)
C35—N3—C36	119.7 (2)	C30—C29—C34	121.8 (3)
C45—N4—C48	119.0 (2)	C29—C30—C31	118.5 (3)
Cl1—C1—C6	118.0 (2)	C30—C31—C32	121.4 (3)
C2—C1—C6	121.8 (3)	C31—C32—C33	119.0 (3)
Cl1—C1—C2	120.2 (2)	C31—C32—C35	120.3 (2)
C1—C2—C3	118.9 (3)	C33—C32—C35	120.6 (2)
C2—C3—C4	120.8 (3)	C32—C33—C34	120.4 (3)
C3—C4—C5	118.6 (2)	C29—C34—C33	119.0 (3)
C3—C4—C7	120.1 (2)	N3—C35—C32	121.2 (2)
C5—C4—C7	121.3 (2)	N3—C36—C37	123.9 (2)
C4—C5—C6	121.4 (3)	N3—C36—C41	117.4 (2)
C1—C6—C5	118.6 (2)	C37—C36—C41	118.6 (2)
N1—C7—C4	121.6 (2)	C36—C37—C38	120.8 (2)
N1—C8—C9	118.5 (2)	C37—C38—C39	121.1 (2)
N1—C8—C13	123.1 (2)	C38—C39—C40	118.3 (2)
C9—C8—C13	118.1 (2)	C38—C39—C42	121.6 (2)
C8—C9—C10	120.1 (2)	C40—C39—C42	120.2 (2)
O1—C9—C8	115.3 (2)	C39—C40—C41	120.9 (2)
O1—C9—C10	124.6 (2)	O3—C41—C36	115.1 (2)
C9—C10—C11	121.5 (2)	O3—C41—C40	124.6 (2)
C10—C11—C12	118.1 (2)	C36—C41—C40	120.3 (2)
C10—C11—C14	120.2 (2)	C39—C42—C43	121.5 (2)
C12—C11—C14	121.7 (2)	C39—C42—C47	120.1 (2)
C11—C12—C13	120.6 (2)	C43—C42—C47	118.4 (2)
C8—C13—C12	121.7 (2)	C42—C43—C44	120.9 (2)
C11—C14—C19	120.5 (2)	C43—C44—C45	121.2 (2)
C15—C14—C19	118.1 (2)	N4—C45—C44	122.9 (2)
C11—C14—C15	121.4 (2)	N4—C45—C46	118.6 (2)
C14—C15—C16	120.4 (2)	C44—C45—C46	118.2 (2)
C15—C16—C17	121.8 (3)	O4—C46—C45	115.3 (2)
N2—C17—C18	118.6 (2)	O4—C46—C47	124.3 (2)
C16—C17—C18	118.0 (2)	C45—C46—C47	120.5 (2)
N2—C17—C16	123.2 (2)	C42—C47—C46	120.9 (2)
C17—C18—C19	120.0 (2)	N4—C48—C49	120.9 (2)
O2—C18—C19	124.8 (2)	C48—C49—C50	120.1 (3)
O2—C18—C17	115.2 (2)	C48—C49—C54	121.3 (3)
C14—C19—C18	121.7 (3)	C50—C49—C54	118.6 (3)
N2—C20—C21	121.4 (3)	C49—C50—C51	120.8 (3)
C20—C21—C22	120.3 (3)	C50—C51—C52	118.8 (4)
C20—C21—C26	121.6 (3)	Cl4—C52—C51	119.4 (3)
C22—C21—C26	118.1 (3)	Cl4—C52—C53	118.9 (3)
C21—C22—C23	120.9 (3)	C51—C52—C53	121.8 (4)
C22—C23—C24	119.3 (3)	C52—C53—C54	118.9 (3)
Cl2—C24—C25	119.5 (2)	C49—C54—C53	121.1 (3)
C23—C24—C25	121.3 (3)	C29—C30—H30	121.00
Cl2—C24—C23	119.2 (3)	C31—C30—H30	121.00
C24—C25—C26	118.9 (3)	C30—C31—H31	119.00
C21—C26—C25	121.5 (3)	C32—C31—H31	119.00
C3—C2—H2	121.00	C32—C33—H33	120.00
C1—C2—H2	121.00	C34—C33—H33	120.00
C4—C3—H3	120.00	C29—C34—H34	121.00
C2—C3—H3	120.00	C33—C34—H34	121.00
C4—C5—H5	119.00	N3—C35—H35	119.00
C6—C5—H5	119.00	C32—C35—H35	119.00
C1—C6—H6	121.00	C36—C37—H37	120.00
C5—C6—H6	121.00	C38—C37—H37	120.00
N1—C7—H7	119.00	C37—C38—H38	120.00
C4—C7—H7	119.00	C39—C38—H38	119.00
C11—C10—H10	119.00	C39—C40—H40	120.00
C9—C10—H10	119.00	C41—C40—H40	120.00
C11—C12—H12	120.00	C42—C43—H43	120.00
C13—C12—H12	120.00	C44—C43—H43	120.00
C12—C13—H13	119.00	C43—C44—H44	119.00
C8—C13—H13	119.00	C45—C44—H44	119.00
C14—C15—H15	120.00	C42—C47—H47	120.00
C16—C15—H15	120.00	C46—C47—H47	120.00
C17—C16—H16	119.00	N4—C48—H48	120.00
C15—C16—H16	119.00	C49—C48—H48	120.00
C14—C19—H19	119.00	C49—C50—H50	120.00
C18—C19—H19	119.00	C51—C50—H50	120.00
N2—C20—H20	119.00	C50—C51—H51	121.00
C21—C20—H20	119.00	C52—C51—H51	121.00
C21—C22—H22	120.00	C52—C53—H53	121.00
C23—C22—H22	120.00	C54—C53—H53	120.00
C24—C23—H23	120.00	C49—C54—H54	119.00
C22—C23—H23	120.00	C53—C54—H54	119.00
C24—C25—H25	121.00	O3—C55—H55A	109.00
C26—C25—H25	121.00	O3—C55—H55B	109.00
C25—C26—H26	119.00	O3—C55—H55C	109.00
C21—C26—H26	119.00	H55A—C55—H55B	109.00
O1—C27—H27B	110.00	H55A—C55—H55C	110.00
O1—C27—H27C	109.00	H55B—C55—H55C	109.00
H27A—C27—H27B	110.00	O4—C56—H56A	109.00
H27A—C27—H27C	109.00	O4—C56—H56B	109.00
O1—C27—H27A	109.00	O4—C56—H56C	109.00
H27B—C27—H27C	109.00	H56A—C56—H56B	110.00
H28A—C28—H28C	109.00	H56A—C56—H56C	109.00
H28B—C28—H28C	109.00	H56B—C56—H56C	110.00
C27—O1—C9—C8	177.9 (3)	C26—C21—C22—C23	−0.2 (4)
C27—O1—C9—C10	−1.0 (4)	C20—C21—C22—C23	−178.8 (3)
C28—O2—C18—C17	177.6 (2)	C22—C21—C26—C25	0.9 (4)
C28—O2—C18—C19	−2.5 (4)	C20—C21—C26—C25	179.5 (2)
C55—O3—C41—C40	−0.8 (4)	C21—C22—C23—C24	−0.8 (5)
C55—O3—C41—C36	177.5 (2)	C22—C23—C24—C25	1.1 (4)
C56—O4—C46—C47	0.7 (4)	C22—C23—C24—Cl2	−179.6 (2)
C56—O4—C46—C45	−177.9 (2)	Cl2—C24—C25—C26	−179.7 (2)
C8—N1—C7—C4	−173.7 (2)	C23—C24—C25—C26	−0.4 (4)
C7—N1—C8—C13	45.5 (4)	C24—C25—C26—C21	−0.6 (4)
C7—N1—C8—C9	−141.9 (3)	Cl3—C29—C30—C31	179.4 (3)
C20—N2—C17—C18	138.2 (3)	C34—C29—C30—C31	0.0 (5)
C17—N2—C20—C21	175.3 (2)	Cl3—C29—C34—C33	−178.9 (2)
C20—N2—C17—C16	−48.2 (4)	C30—C29—C34—C33	0.6 (5)
C35—N3—C36—C41	−136.3 (3)	C29—C30—C31—C32	−0.6 (5)
C36—N3—C35—C32	−178.7 (2)	C30—C31—C32—C33	0.6 (4)
C35—N3—C36—C37	47.5 (4)	C30—C31—C32—C35	178.7 (3)
C45—N4—C48—C49	−176.4 (2)	C31—C32—C33—C34	0.0 (4)
C48—N4—C45—C46	−137.8 (3)	C35—C32—C33—C34	−178.1 (3)
C48—N4—C45—C44	48.1 (4)	C31—C32—C35—N3	−177.4 (3)
C2—C1—C6—C5	0.4 (4)	C33—C32—C35—N3	0.7 (4)
Cl1—C1—C2—C3	−179.2 (3)	C32—C33—C34—C29	−0.6 (4)
Cl1—C1—C6—C5	−180.0 (2)	N3—C36—C37—C38	176.7 (3)
C6—C1—C2—C3	0.5 (5)	C41—C36—C37—C38	0.6 (4)
C1—C2—C3—C4	−1.5 (5)	N3—C36—C41—O3	4.6 (4)
C2—C3—C4—C5	1.7 (5)	N3—C36—C41—C40	−177.0 (3)
C2—C3—C4—C7	−178.2 (3)	C37—C36—C41—O3	−179.0 (2)
C3—C4—C5—C6	−0.8 (4)	C37—C36—C41—C40	−0.6 (4)
C5—C4—C7—N1	−3.2 (4)	C36—C37—C38—C39	−0.4 (4)
C7—C4—C5—C6	179.0 (2)	C37—C38—C39—C40	0.4 (4)
C3—C4—C7—N1	176.7 (3)	C37—C38—C39—C42	179.6 (3)
C4—C5—C6—C1	−0.2 (4)	C38—C39—C40—C41	−0.4 (4)
C13—C8—C9—O1	−179.3 (2)	C42—C39—C40—C41	−179.7 (3)
N1—C8—C9—O1	7.7 (4)	C38—C39—C42—C43	−142.5 (3)
N1—C8—C9—C10	−173.3 (3)	C38—C39—C42—C47	38.6 (4)
C9—C8—C13—C12	−0.3 (4)	C40—C39—C42—C43	36.7 (4)
C13—C8—C9—C10	−0.4 (4)	C40—C39—C42—C47	−142.2 (3)
N1—C8—C13—C12	172.3 (3)	C39—C40—C41—O3	178.8 (2)
C8—C9—C10—C11	1.0 (4)	C39—C40—C41—C36	0.6 (4)
O1—C9—C10—C11	179.8 (3)	C39—C42—C43—C44	−179.8 (2)
C9—C10—C11—C12	−0.9 (4)	C47—C42—C43—C44	−0.9 (4)
C9—C10—C11—C14	178.5 (3)	C39—C42—C47—C46	178.2 (2)
C10—C11—C12—C13	0.3 (4)	C43—C42—C47—C46	−0.8 (4)
C10—C11—C14—C15	−34.9 (4)	C42—C43—C44—C45	1.7 (4)
C10—C11—C14—C19	143.5 (3)	C43—C44—C45—N4	173.4 (2)
C12—C11—C14—C15	144.5 (3)	C43—C44—C45—C46	−0.8 (4)
C12—C11—C14—C19	−37.1 (4)	N4—C45—C46—O4	3.4 (3)
C14—C11—C12—C13	−179.2 (3)	N4—C45—C46—C47	−175.3 (2)
C11—C12—C13—C8	0.4 (4)	C44—C45—C46—O4	177.9 (2)
C11—C14—C15—C16	178.6 (2)	C44—C45—C46—C47	−0.8 (4)
C15—C14—C19—C18	1.1 (4)	O4—C46—C47—C42	−176.9 (2)
C11—C14—C19—C18	−177.4 (2)	C45—C46—C47—C42	1.6 (4)
C19—C14—C15—C16	0.2 (4)	N4—C48—C49—C50	−160.4 (3)
C14—C15—C16—C17	−1.2 (4)	N4—C48—C49—C54	18.7 (4)
C15—C16—C17—C18	0.9 (4)	C48—C49—C50—C51	177.2 (3)
C15—C16—C17—N2	−172.7 (2)	C54—C49—C50—C51	−2.0 (5)
N2—C17—C18—O2	−5.7 (3)	C48—C49—C54—C53	−178.2 (3)
N2—C17—C18—C19	174.3 (2)	C50—C49—C54—C53	0.9 (4)
C16—C17—C18—O2	−179.7 (2)	C49—C50—C51—C52	1.3 (5)
C16—C17—C18—C19	0.4 (4)	C50—C51—C52—Cl4	−180.0 (3)
C17—C18—C19—C14	−1.4 (4)	C50—C51—C52—C53	0.5 (6)
O2—C18—C19—C14	178.7 (2)	Cl4—C52—C53—C54	178.9 (3)
N2—C20—C21—C22	164.9 (3)	C51—C52—C53—C54	−1.5 (5)
N2—C20—C21—C26	−13.7 (4)	C52—C53—C54—C49	0.8 (5)

Cg2, Cg5 and Cg7 are the centroids of the C8–C13, C29–C34 and C42–C47 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C23—H23···O4iii	0.95	2.48	3.348 (4)	152
C31—H31···N1iv	0.95	2.57	3.498 (4)	166
C3—H3···Cg5v	0.95	2.75	3.642 (3)	156
C30—H30···Cg2iv	0.95	2.90	3.641 (3)	136
C33—H33···Cg7vi	0.95	2.97	3.850 (3)	154

Table 1

Hydrogen-bond geometry (Å, °)

Cg2, Cg5 and Cg7 are the centroids of the C8–C13, C29–C34 and C42–C47 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C23—H23⋯O4i	0.95	2.48	3.348 (4)	152
C31—H31⋯N1ii	0.95	2.57	3.498 (4)	166
C3—H3⋯Cg5iii	0.95	2.75	3.642 (3)	156
C30—H30⋯Cg2ii	0.95	2.90	3.641 (3)	136
C33—H33⋯Cg7iv	0.95	2.97	3.850 (3)	154

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