Crystal structure of (E)-1-[4-({4-[(4-meth-oxy-benzyl-idene)amino]-phen-yl}sulfan-yl)phen-yl]ethan-1-one.

The title Schiff base compound, C22H19NO2S, crystallized with two independent mol-ecules (A and B) in the asymmetric unit. Both mol-ecules have an E conformation about the C=N bond. The two mol-ecules differ in the orientation of the aromatic rings with respect to each other. The outer 4-meth-oxy-benzene ring is inclined to the central benzene ring and the outer 4-acetyl-benzene ring by 1.80 (19) and 63.73 (19)°, respectively, in mol-ecule A, and by 6.72 (18) and 68.53 (19)°, respectively, in mol-ecule B. The two outer benzene rings are inclined to one another by 63.77 (18) and 63.19 (18)° in mol-ecules A and B, respectively. In the crystal, the individual mol-ecules stack in columns along [010], and are linked by a number of C-H⋯π inter-actions, forming slabs lying parallel to (001).

Related literature

For the synthesis and structures of Schiff bases, see, for example: Kahwa et al. (1986 ▸). For their use as protein and enzyme mimics, see: Santos et al. (2001 ▸). For their use as corrosion inhibitors, see: Ahamad et al. (2010 ▸); Negm et al. (2010 ▸). For their coordination properties, see: Özkar et al. (2004 ▸); Hebbachi & Benali-Cherif (2005 ▸). For complexation of Schiff bases with transition metals, see: Izatt et al. (1995 ▸); Kalcher et al. (1995 ▸). For the crystal structure of a very similar Schiff base compound derived from 4-amino-4-acetyl­diphenyl sulfide, see: Hebbachi et al. (2013 ▸).

Experimental

Crystal data

C22H19NO2S

M = 361.44

Triclinic,

a = 5.7708 (2) Å

b = 8.0867 (3) Å

c = 19.6929 (8) Å

α = 81.844 (2)°

β = 86.664 (3)°

γ = 85.662 (3)°

V = 906.05 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.20 mm−1

T = 293 K

0.1 × 0.1 × 0.1 mm

Data collection

Bruker SMART 1K CCD area-detector diffractometer

19586 measured reflections

6013 independent reflections

4850 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.076

S = 1.03

6013 reflections

473 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack x determined using 1952 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▸)

Absolute structure parameter: 0.06 (3)

Data collection: SMART (Bruker, 2006 ▸); cell refinement: SAINT (Bruker, 2006 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸) and SHELXL2014.

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S205698901500033X/su5056sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901500033X/su5056Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S205698901500033X/su5056Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S205698901500033X/su5056fig1.tif

The mol­ecular structure of the two independent mol­ecules (A and B) of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

b . DOI: 10.1107/S205698901500033X/su5056fig2.tif

A view along the b axis of the crystal packing of the title compound. C-H⋯π inter­actions are shown as dashed lines (see Table 1 for details; mol­ecule A is red; mol­ecule B is blue; H atoms not involved in these inter­actions have been omitted for clarity).

CCDC reference: 1042562

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

C22H19NO2S	Z = 2
Mr = 361.44	F(000) = 380
Triclinic, P1	Dx = 1.325 Mg m−3
a = 5.7708 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.0867 (3) Å	θ = 1.0–27.1°
c = 19.6929 (8) Å	µ = 0.20 mm−1
α = 81.844 (2)°	T = 293 K
β = 86.664 (3)°	Prism, colourless
γ = 85.662 (3)°	0.1 × 0.1 × 0.1 mm
V = 906.05 (6) Å3

Bruker SMART 1K CCD area-detector diffractometer	4850 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 25.0°, θmin = 2.6°
ω scan	h = −6→6
19586 measured reflections	k = −9→9
6013 independent reflections	l = −22→23

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.039	w = 1/[σ2(Fo2) + (0.0319P)2 + 0.0416P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.076	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.14 e Å−3
6013 reflections	Δρmin = −0.19 e Å−3
473 parameters	Absolute structure: Flack x determined using 1952 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
3 restraints	Absolute structure parameter: 0.06 (3)

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.

	x	y	z	Uiso*/Ueq
S1	0.40421 (16)	0.84717 (13)	0.09943 (5)	0.0521 (3)
O1	1.2589 (5)	0.9295 (3)	0.65028 (13)	0.0582 (8)
O2	1.1549 (6)	1.1965 (5)	−0.14550 (16)	0.0981 (13)
N1	0.7980 (6)	0.9227 (4)	0.36608 (16)	0.0474 (8)
C1	0.9871 (7)	0.8570 (5)	0.38833 (19)	0.0467 (10)
H1	1.0810	0.7913	0.3612	0.056*
C2	1.0659 (6)	0.8797 (5)	0.45527 (18)	0.0410 (9)
C3	0.9313 (7)	0.9756 (5)	0.49822 (19)	0.0473 (10)
H3	0.7912	1.0293	0.4835	0.057*
C4	1.0031 (7)	0.9914 (5)	0.5619 (2)	0.0474 (10)
H4	0.9124	1.0569	0.5898	0.057*
C5	1.2101 (7)	0.9106 (5)	0.58501 (18)	0.0418 (10)
C6	1.3488 (7)	0.8174 (5)	0.54288 (19)	0.0513 (11)
H6	1.4893	0.7645	0.5577	0.062*
C7	1.2765 (7)	0.8037 (5)	0.4784 (2)	0.0519 (10)
H7	1.3709	0.7422	0.4498	0.062*
C8	1.4655 (8)	0.8448 (6)	0.6785 (2)	0.0705 (13)
H8A	1.4721	0.8630	0.7255	0.106*
H8B	1.5993	0.8877	0.6526	0.106*
H8C	1.4638	0.7271	0.6764	0.106*
C9	0.7237 (6)	0.9003 (4)	0.30085 (18)	0.0395 (9)
C10	0.5119 (6)	0.9821 (5)	0.28283 (19)	0.0454 (10)
H10	0.4293	1.0456	0.3132	0.054*
C11	0.4219 (6)	0.9703 (5)	0.22036 (19)	0.0446 (10)
H11	0.2796	1.0260	0.2089	0.054*
C12	0.5420 (6)	0.8762 (5)	0.17482 (18)	0.0404 (9)
C13	0.7546 (6)	0.7946 (5)	0.19237 (19)	0.0462 (10)
H13	0.8370	0.7312	0.1619	0.055*
C14	0.8444 (6)	0.8068 (5)	0.25442 (19)	0.0446 (10)
H14	0.9876	0.7520	0.2655	0.054*
C15	0.5884 (6)	0.9284 (4)	0.02990 (18)	0.0392 (9)
C16	0.7859 (6)	1.0131 (4)	0.03509 (18)	0.0417 (9)
H16	0.8307	1.0313	0.0779	0.050*
C17	0.9151 (6)	1.0700 (5)	−0.02354 (19)	0.0474 (10)
H17	1.0464	1.1273	−0.0196	0.057*
C18	0.8547 (6)	1.0441 (5)	−0.08816 (19)	0.0456 (10)
C19	0.6550 (7)	0.9614 (5)	−0.09213 (19)	0.0489 (10)
H19	0.6093	0.9443	−0.1350	0.059*
C20	0.5227 (7)	0.9041 (5)	−0.03450 (19)	0.0475 (10)
H20	0.3894	0.8491	−0.0386	0.057*
C21	1.0007 (8)	1.1056 (6)	−0.1499 (2)	0.0569 (11)
C22	0.9573 (9)	1.0531 (6)	−0.2177 (2)	0.0800 (15)
H22A	1.0659	1.1021	−0.2522	0.120*
H22B	0.8016	1.0901	−0.2302	0.120*
H22C	0.9767	0.9333	−0.2144	0.120*
S2	−0.10116 (16)	0.32763 (13)	0.16371 (5)	0.0510 (3)
O3	0.8434 (5)	0.4410 (4)	0.69853 (14)	0.0654 (8)
O4	0.2586 (6)	0.6780 (4)	−0.14986 (14)	0.0845 (10)
N2	0.4418 (5)	0.4400 (4)	0.40143 (16)	0.0475 (8)
C23	0.4230 (7)	0.3483 (5)	0.4586 (2)	0.0528 (11)
H23	0.3251	0.2609	0.4627	0.063*
C24	0.5470 (7)	0.3721 (5)	0.51887 (19)	0.0446 (10)
C25	0.7361 (7)	0.4704 (5)	0.5146 (2)	0.0490 (10)
H25	0.7923	0.5194	0.4718	0.059*
C26	0.8425 (7)	0.4964 (5)	0.57344 (19)	0.0487 (10)
H26	0.9686	0.5627	0.5701	0.058*
C27	0.7591 (7)	0.4226 (5)	0.6370 (2)	0.0466 (10)
C28	0.5749 (7)	0.3232 (5)	0.6414 (2)	0.0539 (11)
H28	0.5203	0.2723	0.6840	0.065*
C29	0.4705 (7)	0.2986 (5)	0.5829 (2)	0.0557 (11)
H29	0.3458	0.2310	0.5866	0.067*
C30	1.0244 (8)	0.5508 (6)	0.6994 (2)	0.0753 (14)
H30A	1.0722	0.5461	0.7456	0.113*
H30B	0.9687	0.6632	0.6826	0.113*
H30C	1.1544	0.5171	0.6706	0.113*
C31	0.3062 (6)	0.4115 (4)	0.34626 (18)	0.0399 (9)
C32	0.3869 (6)	0.4741 (4)	0.28040 (18)	0.0429 (9)
H32	0.5214	0.5320	0.2746	0.052*
C33	0.2704 (6)	0.4515 (5)	0.22338 (19)	0.0422 (9)
H33	0.3268	0.4939	0.1797	0.051*
C34	0.0701 (6)	0.3659 (4)	0.23136 (17)	0.0362 (9)
C35	−0.0163 (6)	0.3070 (5)	0.29683 (18)	0.0428 (10)
H35	−0.1530	0.2516	0.3025	0.051*
C36	0.1005 (6)	0.3307 (5)	0.35358 (18)	0.0455 (10)
H36	0.0405	0.2920	0.3973	0.055*
C37	0.0526 (6)	0.4036 (4)	0.08628 (17)	0.0385 (9)
C38	0.2689 (6)	0.3346 (5)	0.06659 (18)	0.0438 (9)
H38	0.3481	0.2541	0.0969	0.053*
C39	0.3663 (7)	0.3849 (5)	0.00259 (19)	0.0434 (10)
H39	0.5111	0.3369	−0.0101	0.052*
C40	0.2549 (6)	0.5052 (5)	−0.04367 (17)	0.0396 (9)
C41	0.0402 (7)	0.5757 (5)	−0.02320 (19)	0.0476 (10)
H41	−0.0369	0.6583	−0.0531	0.057*
C42	−0.0611 (7)	0.5250 (5)	0.04106 (19)	0.0465 (10)
H42	−0.2059	0.5726	0.0539	0.056*
C43	0.3520 (7)	0.5607 (5)	−0.1144 (2)	0.0515 (10)
C44	0.5658 (8)	0.4716 (6)	−0.1407 (2)	0.0737 (14)
H44A	0.5995	0.5168	−0.1877	0.111*
H44B	0.5421	0.3545	−0.1378	0.111*
H44C	0.6939	0.4859	−0.1136	0.111*

	U11	U22	U33	U12	U13	U23
S1	0.0437 (6)	0.0641 (8)	0.0497 (6)	−0.0147 (5)	−0.0073 (5)	−0.0046 (5)
O1	0.064 (2)	0.069 (2)	0.0441 (17)	−0.0068 (16)	−0.0058 (15)	−0.0138 (14)
O2	0.085 (3)	0.149 (4)	0.062 (2)	−0.049 (3)	0.0066 (19)	−0.001 (2)
N1	0.046 (2)	0.052 (2)	0.0449 (19)	−0.0003 (17)	−0.0026 (17)	−0.0098 (16)
C1	0.053 (3)	0.044 (3)	0.043 (2)	0.002 (2)	0.002 (2)	−0.0083 (18)
C2	0.042 (2)	0.040 (2)	0.040 (2)	−0.0033 (18)	0.0031 (19)	−0.0058 (18)
C3	0.044 (2)	0.046 (3)	0.051 (3)	0.0025 (19)	0.001 (2)	−0.007 (2)
C4	0.048 (3)	0.047 (3)	0.048 (2)	−0.002 (2)	0.008 (2)	−0.0152 (19)
C5	0.047 (3)	0.041 (2)	0.039 (2)	−0.011 (2)	−0.002 (2)	−0.0073 (18)
C6	0.046 (2)	0.060 (3)	0.047 (2)	0.005 (2)	−0.007 (2)	−0.011 (2)
C7	0.053 (3)	0.053 (3)	0.050 (2)	0.006 (2)	0.000 (2)	−0.014 (2)
C8	0.073 (3)	0.085 (4)	0.056 (3)	−0.014 (3)	−0.017 (3)	−0.006 (2)
C9	0.039 (2)	0.039 (2)	0.040 (2)	−0.0044 (18)	0.0025 (19)	−0.0066 (17)
C10	0.041 (2)	0.044 (3)	0.050 (2)	0.0023 (19)	0.003 (2)	−0.0083 (19)
C11	0.033 (2)	0.047 (3)	0.050 (3)	0.0010 (18)	−0.001 (2)	0.0019 (19)
C12	0.040 (2)	0.040 (2)	0.040 (2)	−0.0035 (19)	−0.0002 (19)	−0.0033 (18)
C13	0.045 (3)	0.049 (3)	0.046 (2)	0.002 (2)	−0.001 (2)	−0.0119 (19)
C14	0.039 (2)	0.045 (3)	0.048 (2)	0.0059 (19)	−0.006 (2)	−0.006 (2)
C15	0.041 (2)	0.037 (2)	0.041 (2)	0.0025 (18)	−0.0080 (18)	−0.0080 (17)
C16	0.041 (2)	0.047 (2)	0.040 (2)	−0.0034 (19)	−0.0093 (19)	−0.0110 (18)
C17	0.040 (2)	0.059 (3)	0.046 (2)	−0.009 (2)	−0.006 (2)	−0.011 (2)
C18	0.045 (2)	0.049 (3)	0.042 (2)	0.006 (2)	−0.0108 (19)	−0.0064 (19)
C19	0.054 (3)	0.055 (3)	0.039 (2)	−0.001 (2)	−0.015 (2)	−0.0109 (19)
C20	0.047 (3)	0.050 (3)	0.048 (3)	−0.004 (2)	−0.015 (2)	−0.012 (2)
C21	0.054 (3)	0.065 (3)	0.050 (3)	0.005 (2)	−0.005 (2)	−0.003 (2)
C22	0.114 (4)	0.078 (4)	0.047 (3)	0.001 (3)	−0.002 (3)	−0.010 (2)
S2	0.0423 (6)	0.0712 (8)	0.0421 (6)	−0.0166 (5)	−0.0022 (5)	−0.0097 (5)
O3	0.078 (2)	0.073 (2)	0.0477 (18)	−0.0194 (17)	−0.0165 (16)	−0.0049 (15)
O4	0.118 (3)	0.082 (2)	0.0437 (18)	0.014 (2)	−0.0032 (18)	0.0140 (17)
N2	0.051 (2)	0.053 (2)	0.041 (2)	−0.0030 (16)	−0.0040 (17)	−0.0137 (17)
C23	0.059 (3)	0.045 (3)	0.056 (3)	−0.007 (2)	−0.011 (2)	−0.008 (2)
C24	0.051 (3)	0.037 (2)	0.049 (2)	−0.001 (2)	−0.011 (2)	−0.0106 (19)
C25	0.052 (3)	0.051 (3)	0.043 (2)	−0.001 (2)	0.002 (2)	−0.0062 (19)
C26	0.047 (2)	0.053 (3)	0.047 (3)	−0.009 (2)	−0.004 (2)	−0.008 (2)
C27	0.050 (3)	0.048 (3)	0.044 (2)	−0.001 (2)	−0.008 (2)	−0.0105 (19)
C28	0.061 (3)	0.054 (3)	0.046 (2)	−0.008 (2)	−0.009 (2)	0.000 (2)
C29	0.058 (3)	0.050 (3)	0.059 (3)	−0.013 (2)	−0.012 (2)	0.001 (2)
C30	0.066 (3)	0.097 (4)	0.070 (3)	−0.024 (3)	−0.018 (3)	−0.021 (3)
C31	0.041 (2)	0.039 (2)	0.040 (2)	0.0026 (18)	−0.0019 (18)	−0.0089 (18)
C32	0.038 (2)	0.046 (3)	0.045 (2)	−0.0111 (18)	−0.0022 (19)	−0.0047 (18)
C33	0.040 (2)	0.048 (2)	0.037 (2)	−0.0061 (18)	0.0042 (18)	−0.0023 (17)
C34	0.034 (2)	0.038 (2)	0.036 (2)	0.0002 (18)	−0.0014 (17)	−0.0065 (17)
C35	0.036 (2)	0.048 (3)	0.045 (2)	−0.0100 (18)	0.0006 (19)	−0.0041 (19)
C36	0.044 (2)	0.057 (3)	0.035 (2)	−0.003 (2)	0.0018 (19)	−0.0033 (19)
C37	0.040 (2)	0.042 (2)	0.036 (2)	−0.0046 (18)	−0.0063 (18)	−0.0107 (18)
C38	0.043 (2)	0.045 (2)	0.040 (2)	0.0057 (19)	−0.0080 (19)	0.0012 (17)
C39	0.041 (2)	0.047 (3)	0.042 (2)	0.0021 (19)	−0.0037 (19)	−0.0063 (19)
C40	0.047 (2)	0.039 (2)	0.035 (2)	−0.0056 (18)	−0.0084 (18)	−0.0067 (17)
C41	0.054 (3)	0.045 (3)	0.044 (2)	0.005 (2)	−0.016 (2)	−0.0025 (18)
C42	0.041 (2)	0.049 (3)	0.049 (2)	0.0074 (19)	−0.007 (2)	−0.011 (2)
C43	0.069 (3)	0.050 (3)	0.037 (2)	−0.009 (2)	−0.010 (2)	−0.006 (2)
C44	0.073 (3)	0.092 (4)	0.053 (3)	−0.004 (3)	0.013 (3)	−0.005 (3)

S1—C15	1.765 (4)	S2—C37	1.775 (3)
S1—C12	1.776 (4)	S2—C34	1.779 (3)
O1—C5	1.363 (4)	O3—C27	1.362 (4)
O1—C8	1.430 (5)	O3—C30	1.424 (5)
O2—C21	1.210 (5)	O4—C43	1.207 (5)
N1—C1	1.252 (4)	N2—C23	1.260 (4)
N1—C9	1.417 (4)	N2—C31	1.429 (4)
C1—C2	1.459 (5)	C23—C24	1.464 (5)
C1—H1	0.9300	C23—H23	0.9300
C2—C7	1.391 (5)	C24—C29	1.378 (5)
C2—C3	1.392 (5)	C24—C25	1.389 (5)
C3—C4	1.369 (5)	C25—C26	1.391 (5)
C3—H3	0.9300	C25—H25	0.9300
C4—C5	1.386 (5)	C26—C27	1.385 (5)
C4—H4	0.9300	C26—H26	0.9300
C5—C6	1.381 (5)	C27—C28	1.372 (5)
C6—C7	1.380 (5)	C28—C29	1.376 (5)
C6—H6	0.9300	C28—H28	0.9300
C7—H7	0.9300	C29—H29	0.9300
C8—H8A	0.9600	C30—H30A	0.9600
C8—H8B	0.9600	C30—H30B	0.9600
C8—H8C	0.9600	C30—H30C	0.9600
C9—C10	1.385 (5)	C31—C36	1.388 (5)
C9—C14	1.391 (5)	C31—C32	1.391 (5)
C10—C11	1.381 (5)	C32—C33	1.382 (5)
C10—H10	0.9300	C32—H32	0.9300
C11—C12	1.381 (5)	C33—C34	1.382 (5)
C11—H11	0.9300	C33—H33	0.9300
C12—C13	1.386 (5)	C34—C35	1.387 (5)
C13—C14	1.374 (5)	C35—C36	1.382 (5)
C13—H13	0.9300	C35—H35	0.9300
C14—H14	0.9300	C36—H36	0.9300
C15—C20	1.389 (5)	C37—C42	1.382 (5)
C15—C16	1.389 (5)	C37—C38	1.385 (5)
C16—C17	1.379 (5)	C38—C39	1.370 (5)
C16—H16	0.9300	C38—H38	0.9300
C17—C18	1.387 (5)	C39—C40	1.383 (5)
C17—H17	0.9300	C39—H39	0.9300
C18—C19	1.387 (5)	C40—C41	1.386 (5)
C18—C21	1.486 (5)	C40—C43	1.491 (5)
C19—C20	1.374 (5)	C41—C42	1.384 (5)
C19—H19	0.9300	C41—H41	0.9300
C20—H20	0.9300	C42—H42	0.9300
C21—C22	1.498 (6)	C43—C44	1.485 (6)
C22—H22A	0.9600	C44—H44A	0.9600
C22—H22B	0.9600	C44—H44B	0.9600
C22—H22C	0.9600	C44—H44C	0.9600
C15—S1—C12	105.80 (17)	C37—S2—C34	105.96 (16)
C5—O1—C8	118.5 (3)	C27—O3—C30	118.7 (3)
C1—N1—C9	121.9 (3)	C23—N2—C31	119.6 (3)
N1—C1—C2	122.5 (3)	N2—C23—C24	123.6 (4)
N1—C1—H1	118.8	N2—C23—H23	118.2
C2—C1—H1	118.8	C24—C23—H23	118.2
C7—C2—C3	118.1 (4)	C29—C24—C25	118.2 (3)
C7—C2—C1	120.8 (3)	C29—C24—C23	119.2 (4)
C3—C2—C1	121.1 (3)	C25—C24—C23	122.6 (4)
C4—C3—C2	120.6 (4)	C24—C25—C26	120.9 (4)
C4—C3—H3	119.7	C24—C25—H25	119.5
C2—C3—H3	119.7	C26—C25—H25	119.5
C3—C4—C5	120.5 (4)	C27—C26—C25	119.4 (4)
C3—C4—H4	119.7	C27—C26—H26	120.3
C5—C4—H4	119.7	C25—C26—H26	120.3
O1—C5—C6	124.7 (4)	O3—C27—C28	114.8 (4)
O1—C5—C4	115.4 (3)	O3—C27—C26	125.4 (4)
C6—C5—C4	119.9 (3)	C28—C27—C26	119.8 (4)
C7—C6—C5	119.2 (4)	C27—C28—C29	120.3 (4)
C7—C6—H6	120.4	C27—C28—H28	119.9
C5—C6—H6	120.4	C29—C28—H28	119.9
C6—C7—C2	121.6 (4)	C28—C29—C24	121.4 (4)
C6—C7—H7	119.2	C28—C29—H29	119.3
C2—C7—H7	119.2	C24—C29—H29	119.3
O1—C8—H8A	109.5	O3—C30—H30A	109.5
O1—C8—H8B	109.5	O3—C30—H30B	109.5
H8A—C8—H8B	109.5	H30A—C30—H30B	109.5
O1—C8—H8C	109.5	O3—C30—H30C	109.5
H8A—C8—H8C	109.5	H30A—C30—H30C	109.5
H8B—C8—H8C	109.5	H30B—C30—H30C	109.5
C10—C9—C14	118.5 (3)	C36—C31—C32	118.3 (3)
C10—C9—N1	115.5 (3)	C36—C31—N2	125.3 (3)
C14—C9—N1	126.0 (3)	C32—C31—N2	116.4 (3)
C11—C10—C9	120.8 (3)	C33—C32—C31	121.1 (3)
C11—C10—H10	119.6	C33—C32—H32	119.5
C9—C10—H10	119.6	C31—C32—H32	119.5
C12—C11—C10	120.3 (3)	C34—C33—C32	120.0 (3)
C12—C11—H11	119.8	C34—C33—H33	120.0
C10—C11—H11	119.8	C32—C33—H33	120.0
C11—C12—C13	119.2 (3)	C33—C34—C35	119.6 (3)
C11—C12—S1	118.3 (3)	C33—C34—S2	125.6 (3)
C13—C12—S1	122.2 (3)	C35—C34—S2	114.7 (3)
C14—C13—C12	120.4 (3)	C36—C35—C34	120.0 (4)
C14—C13—H13	119.8	C36—C35—H35	120.0
C12—C13—H13	119.8	C34—C35—H35	120.0
C13—C14—C9	120.7 (3)	C35—C36—C31	120.9 (3)
C13—C14—H14	119.6	C35—C36—H36	119.5
C9—C14—H14	119.6	C31—C36—H36	119.5
C20—C15—C16	119.3 (3)	C42—C37—C38	119.2 (3)
C20—C15—S1	115.1 (3)	C42—C37—S2	117.6 (3)
C16—C15—S1	125.5 (3)	C38—C37—S2	122.8 (3)
C17—C16—C15	119.7 (3)	C39—C38—C37	120.1 (3)
C17—C16—H16	120.2	C39—C38—H38	120.0
C15—C16—H16	120.2	C37—C38—H38	120.0
C16—C17—C18	121.8 (3)	C38—C39—C40	121.7 (3)
C16—C17—H17	119.1	C38—C39—H39	119.2
C18—C17—H17	119.1	C40—C39—H39	119.2
C17—C18—C19	117.5 (3)	C39—C40—C41	117.9 (3)
C17—C18—C21	120.0 (4)	C39—C40—C43	123.4 (3)
C19—C18—C21	122.5 (3)	C41—C40—C43	118.7 (3)
C20—C19—C18	121.8 (3)	C42—C41—C40	121.0 (3)
C20—C19—H19	119.1	C42—C41—H41	119.5
C18—C19—H19	119.1	C40—C41—H41	119.5
C19—C20—C15	119.9 (4)	C37—C42—C41	120.1 (3)
C19—C20—H20	120.1	C37—C42—H42	119.9
C15—C20—H20	120.1	C41—C42—H42	119.9
O2—C21—C18	120.4 (4)	O4—C43—C44	120.1 (4)
O2—C21—C22	120.1 (4)	O4—C43—C40	120.3 (4)
C18—C21—C22	119.5 (4)	C44—C43—C40	119.6 (4)
C21—C22—H22A	109.5	C43—C44—H44A	109.5
C21—C22—H22B	109.5	C43—C44—H44B	109.5
H22A—C22—H22B	109.5	H44A—C44—H44B	109.5
C21—C22—H22C	109.5	C43—C44—H44C	109.5
H22A—C22—H22C	109.5	H44A—C44—H44C	109.5
H22B—C22—H22C	109.5	H44B—C44—H44C	109.5
C9—N1—C1—C2	179.7 (3)	C31—N2—C23—C24	−177.4 (3)
N1—C1—C2—C7	179.5 (4)	N2—C23—C24—C29	162.3 (4)
N1—C1—C2—C3	0.6 (6)	N2—C23—C24—C25	−15.8 (6)
C7—C2—C3—C4	−1.2 (6)	C29—C24—C25—C26	−1.2 (6)
C1—C2—C3—C4	177.8 (3)	C23—C24—C25—C26	176.9 (4)
C2—C3—C4—C5	−0.8 (5)	C24—C25—C26—C27	0.3 (6)
C8—O1—C5—C6	−1.3 (5)	C30—O3—C27—C28	−175.9 (4)
C8—O1—C5—C4	177.8 (4)	C30—O3—C27—C26	3.3 (6)
C3—C4—C5—O1	−177.2 (3)	C25—C26—C27—O3	−178.3 (3)
C3—C4—C5—C6	2.0 (6)	C25—C26—C27—C28	0.8 (6)
O1—C5—C6—C7	178.0 (4)	O3—C27—C28—C29	178.3 (4)
C4—C5—C6—C7	−1.2 (6)	C26—C27—C28—C29	−0.9 (6)
C5—C6—C7—C2	−0.9 (6)	C27—C28—C29—C24	0.0 (6)
C3—C2—C7—C6	2.0 (6)	C25—C24—C29—C28	1.1 (6)
C1—C2—C7—C6	−177.0 (4)	C23—C24—C29—C28	−177.1 (4)
C1—N1—C9—C10	−179.3 (4)	C23—N2—C31—C36	22.6 (5)
C1—N1—C9—C14	0.0 (5)	C23—N2—C31—C32	−159.0 (4)
C14—C9—C10—C11	0.4 (5)	C36—C31—C32—C33	−2.3 (5)
N1—C9—C10—C11	179.7 (3)	N2—C31—C32—C33	179.2 (3)
C9—C10—C11—C12	0.1 (5)	C31—C32—C33—C34	0.1 (5)
C10—C11—C12—C13	−0.4 (5)	C32—C33—C34—C35	1.8 (5)
C10—C11—C12—S1	173.4 (3)	C32—C33—C34—S2	179.4 (3)
C15—S1—C12—C11	121.4 (3)	C37—S2—C34—C33	5.3 (4)
C15—S1—C12—C13	−65.0 (3)	C37—S2—C34—C35	−176.9 (3)
C11—C12—C13—C14	0.2 (5)	C33—C34—C35—C36	−1.5 (5)
S1—C12—C13—C14	−173.3 (3)	S2—C34—C35—C36	−179.4 (3)
C12—C13—C14—C9	0.3 (6)	C34—C35—C36—C31	−0.7 (5)
C10—C9—C14—C13	−0.6 (5)	C32—C31—C36—C35	2.6 (5)
N1—C9—C14—C13	−179.8 (3)	N2—C31—C36—C35	−179.0 (3)
C12—S1—C15—C20	174.3 (3)	C34—S2—C37—C42	−122.2 (3)
C12—S1—C15—C16	−6.2 (4)	C34—S2—C37—C38	64.7 (3)
C20—C15—C16—C17	−0.7 (5)	C42—C37—C38—C39	−1.0 (5)
S1—C15—C16—C17	179.9 (3)	S2—C37—C38—C39	172.0 (3)
C15—C16—C17—C18	−0.5 (6)	C37—C38—C39—C40	0.5 (6)
C16—C17—C18—C19	1.4 (5)	C38—C39—C40—C41	0.6 (6)
C16—C17—C18—C21	−179.2 (4)	C38—C39—C40—C43	−178.5 (4)
C17—C18—C19—C20	−1.1 (6)	C39—C40—C41—C42	−1.1 (5)
C21—C18—C19—C20	179.5 (4)	C43—C40—C41—C42	178.0 (3)
C18—C19—C20—C15	−0.1 (6)	C38—C37—C42—C41	0.4 (5)
C16—C15—C20—C19	1.0 (5)	S2—C37—C42—C41	−173.0 (3)
S1—C15—C20—C19	−179.5 (3)	C40—C41—C42—C37	0.7 (5)
C17—C18—C21—O2	−9.5 (6)	C39—C40—C43—O4	−172.4 (4)
C19—C18—C21—O2	169.9 (4)	C41—C40—C43—O4	8.5 (6)
C17—C18—C21—C22	170.0 (4)	C39—C40—C43—C44	7.1 (6)
C19—C18—C21—C22	−10.6 (6)	C41—C40—C43—C44	−172.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···Cg6i	0.93	3.00	3.734 (4)	137
C26—H26···Cg1	0.93	2.96	3.763 (4)	146
C32—H32···Cg2	0.93	2.98	3.706 (4)	136
C41—H41···Cg3ii	0.93	2.99	3.670 (4)	131

Table 1

Hydrogen-bond geometry (, )

Cg1, Cg2, Cg3 and Cg6 are the centroids of the C2C7, C9C14, C15C20 and C37C42 rings, respectively.

DHA	DH	HA	D A	DHA
C17H17Cg6i	0.93	3.00	3.734(4)	137
C26H26Cg1	0.93	2.96	3.763(4)	146
C32H32Cg2	0.93	2.98	3.706(4)	136
C41H41Cg3ii	0.93	2.99	3.670(4)	131

Symmetry codes: (i) ; (ii) .