5-(4-Cyano-5-dicyano-methyl-ene-2,2-dimethyl-2,5-dihydro-3-fur-yl)-3-(1-methyl-1,4-dihydro-pyridin-4-yl-idene)pent-4-enyl 3,5-bis-(benz-yloxy)benzoate acetonitrile 0.25-solvate: a synchrotron radiation study.

The title compound, C(42)H(36)N(4)O(5)·0.25CH(3)CN, crystallizes with a partial twofold disordered (1/4) acetonitrile solvent of crystallization. The linking atoms to the 3,5-bis-(benz-yloxy)benzoic acid are disordered between two conformations in the ratio 0.780 (6):0.220 (6). In the crystal, the mol-ecules pack using mainly C-H⋯N(cyano) inter-actions coupled with weak C-H⋯O(ether) inter-actions and C-H⋯π inter-actions. A brief comparison is made between a conventional and this synchrotron data collection.

Related literature

For general background, see Kay et al. (2004 ▶); Marder et al. (1993 ▶). For related structures, see: Kay et al. (2008 ▶), Gainsford et al. (2007 ▶, 2008 ▶); Kim et al. (2007 ▶) For synthetic data, see: Clarke et al. (2009 ▶). For details of the PX1 beamline, see: McPhillips et al. (2002 ▶).

Experimental

Crystal data

C42H36N4O5·0.25C2H3N

M = 687.01

Monoclinic,

a = 29.374 (6) Å

b = 15.825 (3) Å

c = 16.317 (3) Å

β = 108.61 (3)°

V = 7188 (3) Å3

Z = 8

Synchrotron radiation

λ = 0.77300 Å

μ = 0.08 mm−1

T = 100 K

0.26 × 0.08 × 0.04 mm

Data collection

ADSC Quantum 210r CCD diffractometer

38733 measured reflections

5381 independent reflections

4076 reflections with I > 2σ(I)

R int = 0.098

θmax = 26.0°

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.167

S = 1.04

5381 reflections

482 parameters

H-atom parameters constrained

Δρmax = 0.91 e Å−3

Δρmin = −0.50 e Å−3

Data collection: ADSC Quantum 210r software (ADSC, 2009 ▶); cell refinement: XDS (Kabsch, 1993 ▶); data reduction: XDS, locally modified software and XPREP (Bruker, 2001 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050430/sj2693sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050430/sj2693Isup2.hkl

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

C42H36N4O5·0.25C2H3N	Z = 8
Mr = 687.01	F(000) = 2892
Monoclinic, C2/c	Dx = 1.270 Mg m−3
Hall symbol: -C 2yc	Synchrotron radiation, λ = 0.77300 Å
a = 29.374 (6) Å	µ = 0.08 mm−1
b = 15.825 (3) Å	T = 100 K
c = 16.317 (3) Å	Needle, black
β = 108.61 (3)°	0.26 × 0.08 × 0.04 mm
V = 7188 (3) Å3

ADSC Quantum 210r CCD diffractometer	4076 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.098
graphite	θmax = 26.0°, θmin = 1.6°
ω scans	h = −33→33
38733 measured reflections	k = −17→17
5381 independent reflections	l = −18→18

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)] = 0.060	H-atom parameters constrained
wR(F2) = 0.167	w = 1/[σ2(Fo2) + (0.0862P)2 + 13.1795P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
5381 reflections	Δρmax = 0.91 e Å−3
482 parameters	Δρmin = −0.50 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0128 (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	Occ. (<1)
O1	0.17400 (7)	0.94070 (11)	0.02908 (12)	0.0290 (5)
O3	0.11459 (9)	0.63005 (13)	0.23553 (15)	0.0475 (7)
O4	0.03753 (7)	0.32537 (12)	0.37018 (13)	0.0330 (5)
O5	0.00478 (8)	0.60170 (12)	0.42819 (14)	0.0361 (5)
N1	0.22209 (10)	0.92896 (14)	−0.22501 (16)	0.0329 (6)
N2	0.19059 (12)	1.12873 (16)	−0.0685 (2)	0.0538 (9)
N3	0.19800 (10)	0.73140 (14)	−0.16212 (16)	0.0324 (6)
N4	0.21359 (9)	0.36102 (13)	−0.10782 (15)	0.0278 (6)
C1	0.21038 (11)	0.94562 (16)	−0.16563 (19)	0.0256 (7)
C2	0.19611 (11)	0.96943 (16)	−0.09403 (18)	0.0267 (7)
C3	0.19290 (12)	1.05714 (18)	−0.0795 (2)	0.0354 (8)
C4	0.17049 (10)	0.79170 (16)	0.02949 (17)	0.0241 (6)
C5	0.16325 (11)	0.86922 (16)	0.07822 (18)	0.0255 (7)
C6	0.18610 (10)	0.91040 (16)	−0.03864 (18)	0.0257 (7)
C7	0.18566 (10)	0.82216 (16)	−0.04015 (17)	0.0234 (6)
C8	0.11152 (12)	0.88153 (18)	0.0772 (2)	0.0331 (7)
H8A	0.1025	0.8352	0.1088	0.050*
H8B	0.0900	0.8818	0.0172	0.050*
H8C	0.1088	0.9355	0.1047	0.050*
C9	0.19856 (12)	0.87367 (17)	0.16911 (18)	0.0335 (8)
H9A	0.1968	0.9296	0.1937	0.050*
H9B	0.2312	0.8639	0.1673	0.050*
H9C	0.1905	0.8304	0.2051	0.050*
C10	0.19329 (11)	0.77332 (16)	−0.10791 (18)	0.0243 (7)
C11	0.16310 (11)	0.71102 (16)	0.05218 (18)	0.0292 (7)
H11	0.1496	0.7033	0.0974	0.035*
C12	0.17441 (11)	0.63825 (16)	0.01213 (18)	0.0265 (7)
H12	0.1922	0.6482	−0.0263	0.032*
C13	0.16333 (13)	0.55628 (17)	0.0211 (2)	0.0395 (9)
C14	0.18049 (11)	0.48951 (17)	−0.02358 (19)	0.0305 (7)
C15	0.20573 (12)	0.50609 (17)	−0.08233 (19)	0.0331 (8)
H15	0.2114	0.5630	−0.0947	0.040*
C16	0.22209 (11)	0.44259 (16)	−0.12181 (19)	0.0305 (7)
H16	0.2398	0.4560	−0.1598	0.037*
C17	0.18892 (11)	0.34164 (16)	−0.05347 (18)	0.0282 (7)
H17	0.1827	0.2841	−0.0444	0.034*
C18	0.17278 (11)	0.40315 (17)	−0.01131 (19)	0.0294 (7)
H18	0.1559	0.3875	0.0273	0.035*
C19	0.23173 (14)	0.29362 (18)	−0.1516 (2)	0.0420 (9)
H19A	0.2652	0.2809	−0.1183	0.063*
H19B	0.2300	0.3125	−0.2098	0.063*
H19C	0.2121	0.2427	−0.1559	0.063*
C22	0.10633 (14)	0.55612 (19)	0.2443 (2)	0.0465 (9)
C23	0.07702 (11)	0.52344 (18)	0.29680 (18)	0.0309 (7)
C24	0.07207 (11)	0.43685 (18)	0.30567 (18)	0.0300 (7)
H24	0.0867	0.3979	0.2776	0.036*
C25	0.04542 (10)	0.40880 (17)	0.35614 (18)	0.0262 (7)
C26	0.02430 (11)	0.46596 (18)	0.39724 (18)	0.0288 (7)
H26	0.0064	0.4461	0.4326	0.035*
C27	0.02924 (10)	0.55180 (17)	0.38689 (18)	0.0275 (7)
C28	0.05616 (10)	0.58211 (18)	0.33736 (17)	0.0278 (7)
H28	0.0602	0.6411	0.3313	0.033*
C29	0.05841 (11)	0.26294 (18)	0.32904 (19)	0.0311 (7)
H29A	0.0938	0.2683	0.3499	0.037*
H29B	0.0471	0.2718	0.2657	0.037*
C30	0.04418 (11)	0.17648 (18)	0.34973 (18)	0.0289 (7)
C31	0.06809 (12)	0.10686 (19)	0.33084 (19)	0.0346 (7)
H31	0.0930	0.1150	0.3062	0.041*
C32	0.05569 (12)	0.02574 (19)	0.3477 (2)	0.0404 (8)
H32	0.0723	−0.0214	0.3350	0.048*
C33	0.01922 (12)	0.01313 (19)	0.3829 (2)	0.0400 (8)
H33	0.0108	−0.0425	0.3946	0.048*
C34	−0.00487 (12)	0.08144 (18)	0.4010 (2)	0.0344 (7)
H34	−0.0301	0.0728	0.4248	0.041*
C35	0.00742 (11)	0.16279 (18)	0.38470 (19)	0.0313 (7)
H35	−0.0094	0.2096	0.3975	0.038*
C36	0.01009 (12)	0.69126 (18)	0.4277 (2)	0.0373 (8)
H36A	−0.0175	0.7178	0.4401	0.045*
H36B	0.0091	0.7092	0.3690	0.045*
C37	0.05594 (11)	0.72330 (17)	0.4923 (2)	0.0310 (7)
C38	0.07674 (13)	0.79806 (19)	0.4777 (2)	0.0419 (9)
H38	0.0645	0.8257	0.4234	0.050*
C39	0.11551 (14)	0.8330 (2)	0.5421 (3)	0.0510 (10)
H39	0.1291	0.8848	0.5317	0.061*
C40	0.13430 (13)	0.7930 (2)	0.6206 (2)	0.0452 (9)
H40	0.1604	0.8175	0.6647	0.054*
C41	0.11505 (11)	0.71712 (19)	0.6349 (2)	0.0365 (8)
H41	0.1287	0.6881	0.6880	0.044*
C42	0.07586 (11)	0.68318 (17)	0.5719 (2)	0.0306 (7)
H42	0.0623	0.6317	0.5831	0.037*
O2A	0.12743 (10)	0.49113 (14)	0.21304 (16)	0.0282 (9)	0.780 (6)
C20A	0.12933 (15)	0.5332 (2)	0.0708 (2)	0.0250 (10)	0.780 (6)
H20A	0.1070	0.5806	0.0687	0.030*	0.780 (6)
H20B	0.1102	0.4830	0.0445	0.030*	0.780 (6)
C21A	0.15854 (14)	0.5148 (2)	0.1632 (3)	0.0282 (10)	0.780 (6)
H21A	0.1813	0.4682	0.1648	0.034*	0.780 (6)
H21B	0.1774	0.5654	0.1893	0.034*	0.780 (6)
O2B	0.0926 (3)	0.5060 (5)	0.1643 (5)	0.019 (2)*	0.220 (6)
C20B	0.1638 (5)	0.5335 (8)	0.1196 (10)	0.019 (2)*	0.220 (6)
H20C	0.1782	0.4778	0.1402	0.022*	0.220 (6)
H20D	0.1786	0.5782	0.1622	0.022*	0.220 (6)
C21B	0.1100 (4)	0.5333 (7)	0.0924 (7)	0.019 (2)*	0.220 (6)
H21C	0.0978	0.5908	0.0735	0.022*	0.220 (6)
H21D	0.0973	0.4946	0.0427	0.022*	0.220 (6)
C1S	0.0950 (4)	0.8005 (7)	0.2786 (7)	0.082 (2)*	0.25
H1S1	0.1110	0.8128	0.3399	0.122*	0.25
H1S2	0.1098	0.8340	0.2434	0.122*	0.25
H1S3	0.0984	0.7402	0.2679	0.122*	0.25
C2S	0.0488 (7)	0.8199 (13)	0.2578 (13)	0.082 (2)*	0.25
N2S	0.0000	0.8254 (7)	0.2500	0.082 (2)*	0.50

	U11	U22	U33	U12	U13	U23
O1	0.0542 (14)	0.0113 (9)	0.0335 (11)	−0.0014 (8)	0.0307 (10)	−0.0023 (8)
O3	0.0843 (19)	0.0267 (13)	0.0502 (14)	−0.0171 (11)	0.0479 (14)	−0.0105 (10)
O4	0.0472 (13)	0.0229 (11)	0.0416 (12)	−0.0021 (9)	0.0320 (11)	−0.0020 (9)
O5	0.0417 (13)	0.0275 (11)	0.0486 (13)	−0.0024 (9)	0.0275 (11)	−0.0090 (9)
N1	0.0529 (17)	0.0207 (12)	0.0339 (15)	−0.0020 (11)	0.0264 (14)	0.0032 (11)
N2	0.096 (3)	0.0168 (15)	0.075 (2)	0.0010 (14)	0.065 (2)	0.0018 (13)
N3	0.0564 (18)	0.0185 (12)	0.0320 (14)	0.0034 (11)	0.0278 (13)	0.0006 (11)
N4	0.0481 (16)	0.0150 (12)	0.0299 (13)	−0.0032 (10)	0.0262 (12)	−0.0014 (10)
C1	0.0384 (17)	0.0120 (13)	0.0318 (16)	−0.0006 (12)	0.0190 (15)	0.0062 (12)
C2	0.0480 (19)	0.0128 (13)	0.0292 (15)	−0.0002 (12)	0.0261 (15)	−0.0002 (11)
C3	0.059 (2)	0.0188 (17)	0.0429 (19)	0.0017 (14)	0.0372 (17)	0.0035 (13)
C4	0.0392 (17)	0.0157 (14)	0.0232 (14)	−0.0017 (12)	0.0182 (13)	−0.0006 (11)
C5	0.0445 (18)	0.0148 (13)	0.0254 (15)	−0.0025 (12)	0.0226 (14)	0.0012 (11)
C6	0.0379 (17)	0.0176 (14)	0.0273 (15)	−0.0007 (12)	0.0185 (14)	−0.0025 (11)
C7	0.0391 (17)	0.0131 (13)	0.0246 (15)	−0.0012 (11)	0.0192 (13)	−0.0016 (11)
C8	0.051 (2)	0.0228 (15)	0.0374 (18)	0.0002 (13)	0.0306 (16)	−0.0021 (13)
C9	0.056 (2)	0.0209 (15)	0.0295 (17)	−0.0008 (14)	0.0217 (16)	−0.0040 (12)
C10	0.0417 (18)	0.0124 (13)	0.0253 (15)	−0.0008 (12)	0.0196 (14)	0.0043 (12)
C11	0.053 (2)	0.0178 (14)	0.0268 (15)	−0.0027 (13)	0.0268 (15)	−0.0001 (12)
C12	0.0448 (18)	0.0183 (14)	0.0241 (15)	−0.0001 (12)	0.0219 (14)	0.0010 (11)
C13	0.075 (2)	0.0164 (15)	0.0474 (19)	−0.0038 (15)	0.0483 (19)	−0.0002 (13)
C14	0.052 (2)	0.0167 (14)	0.0342 (17)	−0.0028 (13)	0.0292 (16)	−0.0011 (12)
C15	0.064 (2)	0.0126 (13)	0.0368 (17)	−0.0090 (13)	0.0352 (17)	−0.0036 (12)
C16	0.052 (2)	0.0177 (14)	0.0328 (16)	−0.0078 (13)	0.0293 (16)	−0.0025 (12)
C17	0.0458 (19)	0.0138 (13)	0.0318 (16)	−0.0041 (12)	0.0220 (15)	−0.0003 (12)
C18	0.0470 (19)	0.0186 (14)	0.0325 (16)	−0.0055 (13)	0.0268 (15)	−0.0003 (12)
C19	0.076 (3)	0.0174 (15)	0.050 (2)	−0.0004 (15)	0.045 (2)	−0.0058 (14)
C22	0.085 (3)	0.0296 (19)	0.044 (2)	−0.0158 (17)	0.047 (2)	−0.0121 (15)
C23	0.0440 (19)	0.0305 (16)	0.0248 (15)	−0.0070 (14)	0.0201 (15)	−0.0043 (13)
C24	0.0406 (18)	0.0285 (16)	0.0298 (16)	−0.0040 (13)	0.0236 (15)	−0.0066 (13)
C25	0.0327 (17)	0.0228 (15)	0.0269 (15)	−0.0044 (12)	0.0150 (14)	0.0004 (12)
C26	0.0322 (17)	0.0306 (16)	0.0300 (16)	−0.0060 (13)	0.0188 (14)	−0.0026 (13)
C27	0.0303 (17)	0.0283 (16)	0.0260 (15)	0.0002 (12)	0.0120 (14)	−0.0044 (12)
C28	0.0378 (18)	0.0256 (15)	0.0225 (15)	−0.0055 (13)	0.0131 (14)	−0.0007 (12)
C29	0.0403 (18)	0.0289 (16)	0.0316 (16)	0.0023 (13)	0.0223 (15)	−0.0007 (13)
C30	0.0345 (17)	0.0289 (16)	0.0278 (16)	0.0013 (13)	0.0163 (14)	−0.0012 (12)
C31	0.0413 (19)	0.0351 (17)	0.0341 (17)	0.0027 (14)	0.0216 (15)	−0.0026 (14)
C32	0.053 (2)	0.0279 (17)	0.046 (2)	0.0078 (15)	0.0244 (18)	−0.0046 (14)
C33	0.053 (2)	0.0254 (16)	0.045 (2)	−0.0016 (15)	0.0217 (18)	−0.0003 (14)
C34	0.0448 (19)	0.0296 (17)	0.0358 (17)	−0.0023 (14)	0.0229 (16)	0.0019 (13)
C35	0.0394 (18)	0.0291 (16)	0.0327 (17)	0.0048 (13)	0.0216 (15)	0.0001 (13)
C36	0.044 (2)	0.0261 (16)	0.049 (2)	0.0071 (14)	0.0245 (17)	−0.0001 (14)
C37	0.0404 (18)	0.0198 (14)	0.0454 (19)	0.0050 (13)	0.0314 (16)	−0.0027 (13)
C38	0.060 (2)	0.0276 (17)	0.051 (2)	0.0024 (16)	0.0357 (19)	0.0044 (15)
C39	0.063 (2)	0.0293 (18)	0.080 (3)	−0.0146 (17)	0.050 (2)	−0.0101 (18)
C40	0.048 (2)	0.043 (2)	0.054 (2)	−0.0058 (16)	0.0307 (19)	−0.0148 (18)
C41	0.0397 (19)	0.0334 (17)	0.0434 (19)	0.0032 (14)	0.0233 (16)	−0.0057 (15)
C42	0.0396 (18)	0.0209 (14)	0.0422 (18)	0.0020 (13)	0.0285 (16)	−0.0024 (13)
O2A	0.045 (2)	0.0226 (13)	0.0289 (16)	−0.0052 (12)	0.0292 (15)	−0.0001 (11)
C20A	0.039 (3)	0.0168 (17)	0.028 (2)	−0.0010 (16)	0.023 (2)	−0.0015 (15)
C21A	0.042 (2)	0.025 (2)	0.026 (2)	−0.0020 (17)	0.0231 (19)	−0.0012 (16)

O1—C6	1.352 (3)	C24—H24	0.9500
O1—C5	1.478 (3)	C25—C26	1.385 (4)
O3—C22	1.212 (4)	C26—C27	1.382 (4)
O4—C25	1.372 (3)	C26—H26	0.9500
O4—C29	1.437 (3)	C27—C28	1.384 (4)
O5—C27	1.380 (3)	C28—H28	0.9500
O5—C36	1.426 (3)	C29—C30	1.500 (4)
N1—C1	1.157 (3)	C29—H29A	0.9900
N2—C3	1.152 (4)	C29—H29B	0.9900
N3—C10	1.149 (3)	C30—C35	1.390 (4)
N4—C17	1.347 (4)	C30—C31	1.393 (4)
N4—C16	1.348 (3)	C31—C32	1.386 (4)
N4—C19	1.475 (3)	C31—H31	0.9500
C1—C2	1.412 (4)	C32—C33	1.382 (5)
C2—C6	1.395 (4)	C32—H32	0.9500
C2—C3	1.417 (4)	C33—C34	1.374 (4)
C4—C11	1.366 (4)	C33—H33	0.9500
C4—C7	1.430 (4)	C34—C35	1.385 (4)
C4—C5	1.513 (4)	C34—H34	0.9500
C5—C9	1.516 (4)	C35—H35	0.9500
C5—C8	1.527 (4)	C36—C37	1.508 (5)
C6—C7	1.397 (4)	C36—H36A	0.9900
C7—C10	1.424 (4)	C36—H36B	0.9900
C8—H8A	0.9800	C37—C38	1.386 (4)
C8—H8B	0.9800	C37—C42	1.396 (4)
C8—H8C	0.9800	C38—C39	1.394 (5)
C9—H9A	0.9800	C38—H38	0.9500
C9—H9B	0.9800	C39—C40	1.378 (5)
C9—H9C	0.9800	C39—H39	0.9500
C11—C12	1.415 (4)	C40—C41	1.378 (5)
C11—H11	0.9500	C40—H40	0.9500
C12—C13	1.357 (4)	C41—C42	1.383 (4)
C12—H12	0.9500	C41—H41	0.9500
C13—C14	1.462 (4)	C42—H42	0.9500
C13—C20A	1.518 (5)	O2A—C21A	1.452 (5)
C13—C20B	1.643 (15)	C20A—C21A	1.507 (6)
C14—C18	1.410 (4)	C20A—H20A	0.9900
C14—C15	1.411 (4)	C20A—H20B	0.9900
C15—C16	1.361 (4)	C21A—H21A	0.9900
C15—H15	0.9500	C21A—H21B	0.9900
C16—H16	0.9500	O2B—C21B	1.486 (14)
C17—C18	1.362 (4)	C20B—C21B	1.498 (17)
C17—H17	0.9500	C20B—H20C	0.9900
C18—H18	0.9500	C20B—H20D	0.9900
C19—H19A	0.9800	C21B—H21C	0.9900
C19—H19B	0.9800	C21B—H21D	0.9900
C19—H19C	0.9800	C1S—C2S	1.33 (2)
C22—O2A	1.380 (4)	C1S—H1S1	0.9800
C22—O2B	1.470 (9)	C1S—H1S2	0.9800
C22—C23	1.488 (4)	C1S—H1S3	0.9800
C23—C24	1.390 (4)	C2S—N2S	1.40 (2)
C23—C28	1.391 (4)	N2S—C2Si	1.40 (2)
C24—C25	1.378 (4)
C6—O1—C5	109.24 (19)	C27—C26—C25	120.1 (3)
C25—O4—C29	117.6 (2)	C27—C26—H26	119.9
C27—O5—C36	119.4 (2)	C25—C26—H26	119.9
C17—N4—C16	119.8 (2)	O5—C27—C26	114.3 (2)
C17—N4—C19	120.5 (2)	O5—C27—C28	124.8 (3)
C16—N4—C19	119.7 (2)	C26—C27—C28	120.9 (3)
N1—C1—C2	177.7 (3)	C27—C28—C23	117.8 (3)
C6—C2—C1	122.5 (2)	C27—C28—H28	121.1
C6—C2—C3	120.5 (2)	C23—C28—H28	121.1
C1—C2—C3	117.0 (2)	O4—C29—C30	109.3 (2)
N2—C3—C2	179.0 (3)	O4—C29—H29A	109.8
C11—C4—C7	130.3 (2)	C30—C29—H29A	109.8
C11—C4—C5	123.7 (2)	O4—C29—H29B	109.8
C7—C4—C5	106.0 (2)	C30—C29—H29B	109.8
O1—C5—C4	104.19 (19)	H29A—C29—H29B	108.3
O1—C5—C9	107.3 (2)	C35—C30—C31	118.7 (3)
C4—C5—C9	112.6 (2)	C35—C30—C29	122.9 (3)
O1—C5—C8	106.3 (2)	C31—C30—C29	118.4 (3)
C4—C5—C8	113.8 (2)	C32—C31—C30	120.4 (3)
C9—C5—C8	111.9 (2)	C32—C31—H31	119.8
O1—C6—C2	117.2 (2)	C30—C31—H31	119.8
O1—C6—C7	111.5 (2)	C33—C32—C31	120.3 (3)
C2—C6—C7	131.4 (2)	C33—C32—H32	119.9
C6—C7—C10	123.6 (2)	C31—C32—H32	119.9
C6—C7—C4	109.1 (2)	C34—C33—C32	119.7 (3)
C10—C7—C4	126.9 (2)	C34—C33—H33	120.1
C5—C8—H8A	109.5	C32—C33—H33	120.1
C5—C8—H8B	109.5	C33—C34—C35	120.4 (3)
H8A—C8—H8B	109.5	C33—C34—H34	119.8
C5—C8—H8C	109.5	C35—C34—H34	119.8
H8A—C8—H8C	109.5	C34—C35—C30	120.5 (3)
H8B—C8—H8C	109.5	C34—C35—H35	119.8
C5—C9—H9A	109.5	C30—C35—H35	119.8
C5—C9—H9B	109.5	O5—C36—C37	113.9 (2)
H9A—C9—H9B	109.5	O5—C36—H36A	108.8
C5—C9—H9C	109.5	C37—C36—H36A	108.8
H9A—C9—H9C	109.5	O5—C36—H36B	108.8
H9B—C9—H9C	109.5	C37—C36—H36B	108.8
N3—C10—C7	177.0 (3)	H36A—C36—H36B	107.7
C4—C11—C12	123.7 (2)	C38—C37—C42	118.1 (3)
C4—C11—H11	118.2	C38—C37—C36	120.7 (3)
C12—C11—H11	118.2	C42—C37—C36	120.9 (3)
C13—C12—C11	129.0 (3)	C37—C38—C39	120.6 (3)
C13—C12—H12	115.5	C37—C38—H38	119.7
C11—C12—H12	115.5	C39—C38—H38	119.7
C12—C13—C14	120.3 (3)	C40—C39—C38	120.5 (3)
C12—C13—C20A	120.6 (3)	C40—C39—H39	119.8
C14—C13—C20A	118.9 (3)	C38—C39—H39	119.8
C12—C13—C20B	112.8 (5)	C39—C40—C41	119.6 (3)
C14—C13—C20B	115.7 (5)	C39—C40—H40	120.2
C18—C14—C15	114.8 (2)	C41—C40—H40	120.2
C18—C14—C13	122.2 (2)	C40—C41—C42	120.1 (3)
C15—C14—C13	123.0 (2)	C40—C41—H41	119.9
C16—C15—C14	121.7 (3)	C42—C41—H41	119.9
C16—C15—H15	119.1	C41—C42—C37	121.1 (3)
C14—C15—H15	119.1	C41—C42—H42	119.4
N4—C16—C15	120.9 (3)	C37—C42—H42	119.4
N4—C16—H16	119.5	C22—O2A—C21A	116.9 (2)
C15—C16—H16	119.5	C21A—C20A—C13	108.7 (3)
N4—C17—C18	121.1 (2)	C21A—C20A—H20A	110.0
N4—C17—H17	119.4	C13—C20A—H20A	110.0
C18—C17—H17	119.4	C21A—C20A—H20B	110.0
C17—C18—C14	121.6 (3)	C13—C20A—H20B	110.0
C17—C18—H18	119.2	H20A—C20A—H20B	108.3
C14—C18—H18	119.2	O2A—C21A—C20A	110.6 (3)
N4—C19—H19A	109.5	O2A—C21A—H21A	109.5
N4—C19—H19B	109.5	C20A—C21A—H21A	109.5
H19A—C19—H19B	109.5	O2A—C21A—H21B	109.5
N4—C19—H19C	109.5	C20A—C21A—H21B	109.5
H19A—C19—H19C	109.5	H21A—C21A—H21B	108.1
H19B—C19—H19C	109.5	C22—O2B—C21B	118.6 (7)
O3—C22—O2A	123.0 (3)	C21B—C20B—C13	91.8 (9)
O3—C22—O2B	115.1 (4)	C21B—C20B—H20C	113.3
O2A—C22—O2B	45.3 (3)	C13—C20B—H20C	113.3
O3—C22—C23	125.3 (3)	C21B—C20B—H20D	113.3
O2A—C22—C23	111.4 (3)	C13—C20B—H20D	113.3
O2B—C22—C23	106.2 (4)	H20C—C20B—H20D	110.6
C24—C23—C28	122.1 (3)	O2B—C21B—C20B	111.3 (10)
C24—C23—C22	120.1 (3)	O2B—C21B—H21C	109.4
C28—C23—C22	117.8 (3)	C20B—C21B—H21C	109.4
C25—C24—C23	118.5 (3)	O2B—C21B—H21D	109.4
C25—C24—H24	120.7	C20B—C21B—H21D	109.4
C23—C24—H24	120.7	H21C—C21B—H21D	108.0
O4—C25—C24	124.6 (2)	C1S—C2S—N2S	166.3 (18)
O4—C25—C26	114.9 (2)	C2Si—N2S—C2S	172.9 (19)
C24—C25—C26	120.4 (3)
C6—O1—C5—C4	−0.3 (3)	C28—C23—C24—C25	0.2 (5)
C6—O1—C5—C9	119.3 (2)	C22—C23—C24—C25	178.8 (3)
C6—O1—C5—C8	−120.8 (2)	C29—O4—C25—C24	−0.2 (4)
C11—C4—C5—O1	−178.4 (3)	C29—O4—C25—C26	179.8 (3)
C7—C4—C5—O1	1.6 (3)	C23—C24—C25—O4	179.8 (3)
C11—C4—C5—C9	65.7 (4)	C23—C24—C25—C26	−0.3 (4)
C7—C4—C5—C9	−114.4 (3)	O4—C25—C26—C27	−179.1 (3)
C11—C4—C5—C8	−63.0 (4)	C24—C25—C26—C27	0.9 (4)
C7—C4—C5—C8	116.9 (3)	C36—O5—C27—C26	175.3 (3)
C5—O1—C6—C2	178.2 (3)	C36—O5—C27—C28	−5.9 (4)
C5—O1—C6—C7	−1.2 (3)	C25—C26—C27—O5	177.3 (3)
C1—C2—C6—O1	178.3 (3)	C25—C26—C27—C28	−1.6 (5)
C3—C2—C6—O1	−0.8 (4)	O5—C27—C28—C23	−177.3 (3)
C1—C2—C6—C7	−2.5 (5)	C26—C27—C28—C23	1.5 (4)
C3—C2—C6—C7	178.4 (3)	C24—C23—C28—C27	−0.9 (5)
O1—C6—C7—C10	174.9 (3)	C22—C23—C28—C27	−179.4 (3)
C2—C6—C7—C10	−4.3 (5)	C25—O4—C29—C30	−178.0 (2)
O1—C6—C7—C4	2.3 (4)	O4—C29—C30—C35	14.4 (4)
C2—C6—C7—C4	−177.0 (3)	O4—C29—C30—C31	−167.4 (3)
C11—C4—C7—C6	177.6 (3)	C35—C30—C31—C32	−0.8 (5)
C5—C4—C7—C6	−2.3 (3)	C29—C30—C31—C32	−179.1 (3)
C11—C4—C7—C10	5.3 (5)	C30—C31—C32—C33	0.5 (5)
C5—C4—C7—C10	−174.7 (3)	C31—C32—C33—C34	0.2 (5)
C7—C4—C11—C12	6.6 (5)	C32—C33—C34—C35	−0.5 (5)
C5—C4—C11—C12	−173.4 (3)	C33—C34—C35—C30	0.1 (5)
C4—C11—C12—C13	−170.8 (3)	C31—C30—C35—C34	0.5 (5)
C11—C12—C13—C14	−177.2 (3)	C29—C30—C35—C34	178.7 (3)
C11—C12—C13—C20A	8.4 (6)	C27—O5—C36—C37	−78.9 (3)
C11—C12—C13—C20B	−35.0 (7)	O5—C36—C37—C38	152.5 (3)
C12—C13—C14—C18	175.4 (3)	O5—C36—C37—C42	−34.0 (4)
C20A—C13—C14—C18	−10.1 (5)	C42—C37—C38—C39	−1.9 (4)
C20B—C13—C14—C18	34.2 (7)	C36—C37—C38—C39	171.8 (3)
C12—C13—C14—C15	−5.0 (5)	C37—C38—C39—C40	1.2 (5)
C20A—C13—C14—C15	169.6 (3)	C38—C39—C40—C41	1.1 (5)
C20B—C13—C14—C15	−146.1 (6)	C39—C40—C41—C42	−2.6 (5)
C18—C14—C15—C16	−1.5 (5)	C40—C41—C42—C37	1.9 (4)
C13—C14—C15—C16	178.8 (3)	C38—C37—C42—C41	0.4 (4)
C17—N4—C16—C15	−0.6 (5)	C36—C37—C42—C41	−173.3 (3)
C19—N4—C16—C15	179.9 (3)	O3—C22—O2A—C21A	−3.8 (5)
C14—C15—C16—N4	1.8 (5)	C23—C22—O2A—C21A	−177.8 (3)
C16—N4—C17—C18	−0.8 (4)	C12—C13—C20A—C21A	−93.6 (4)
C19—N4—C17—C18	178.7 (3)	C14—C13—C20A—C21A	91.9 (4)
N4—C17—C18—C14	1.0 (5)	C22—O2A—C21A—C20A	−82.2 (4)
C15—C14—C18—C17	0.2 (5)	C13—C20A—C21A—O2A	−179.1 (2)
C13—C14—C18—C17	179.9 (3)	O3—C22—O2B—C21B	26.8 (9)
O3—C22—C23—C24	−176.7 (4)	C23—C22—O2B—C21B	170.0 (7)
O2A—C22—C23—C24	−2.8 (5)	C12—C13—C20B—C21B	104.1 (7)
O2B—C22—C23—C24	45.0 (5)	C14—C13—C20B—C21B	−111.9 (7)
O3—C22—C23—C28	1.9 (6)	C22—O2B—C21B—C20B	60.6 (11)
O2A—C22—C23—C28	175.8 (3)	C13—C20B—C21B—O2B	174.5 (7)
O2B—C22—C23—C28	−136.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···N1ii	0.98	2.59	3.529 (4)	161
C9—H9B···N3iii	0.98	2.59	3.497 (5)	153
C16—H16···N1iv	0.95	2.51	3.406 (4)	156
C17—H17···N2v	0.95	2.51	3.380 (4)	152
C19—H19C···N2v	0.98	2.50	3.340 (4)	143
C26—H26···O5vi	0.95	2.51	3.398 (4)	155
C8—H8B···Cg1vii	0.98	2.54	3.515 (3)	171

Plane	C1–C12,N1–N3,O1	C12–C19,N4	C22–C30,O3–O4	C29–C35	C37–C42	SIGPa,Å
C1–C12,N1–N3,O1		14.59 (10)	18.77 (7)	31.92 (12)	64.58 (13)	0.025 (3)
C12–C19,N4	14.59 (10)		4.90 (9)	18.33 (13)	75.25 (15)	0.033 (3)
C22–C30,O3–O4	18.77 (7)	4.90 (9)		13.48 (11)	80.11 (12)	0.026 (3)
C29–C35b	31.92 (12)	18.33 (13)	13.48 (11)		86.94 (16)	0.004 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯N1i	0.98	2.59	3.529 (4)	161
C9—H9B⋯N3ii	0.98	2.59	3.497 (5)	153
C16—H16⋯N1iii	0.95	2.51	3.406 (4)	156
C17—H17⋯N2iv	0.95	2.51	3.380 (4)	152
C19—H19C⋯N2iv	0.98	2.50	3.340 (4)	143
C26—H26⋯O5v	0.95	2.51	3.398 (4)	155
C8—H8B⋯Cg1vi	0.98	2.54	3.515 (3)	171

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) . Cg1 is the centroid of the C30–C35 ring.

Table 2

Inter­planar angles and SIGP values for the planar entities (Å, °)

Plane	P1	P2	P3	P4	P5	SIGPa
P1		14.59 (10)	18.77 (7)	31.92 (12)	64.58 (13)	0.025 (3)
P2	14.59 (10)		4.90 (9)	18.33 (13)	75.25 (15)	0.033 (3)
P3	18.77 (7)	4.90 (9)		13.48 (11)	80.11 (12)	0.026 (3)
P4b	31.92 (12)	18.33 (13)	13.48 (11)		86.94 (16)	0.004 (3)

Notes: P1 = C1–C12,N1–N3,O1; P2 = C12–C19,N4; P3 = C22–C30,O3–O4; P4 = C29–C35; P5 = C37–C42. (a) (Spek, 2009 ▶); (b) SIGP for plane C37–C42 is 0.014 (3) Å.