2-{2-[5-(4-Cyano-5-di-cyano-methyl-idene-2,2-dimethyl-2,5-di-hydro-furan-3-yl)penta-2,4-dienyl-idene]-3,3-dimethyl-2,3-di-hydro-1H-indol-1-yl}ethyl 3,5-bis-(benz-yloxy)benzoate.

In the title mol-ecule, C48H42N4O5, a potential non-linear optical compound, the furan ring [r.m.s. deviation = 0.010 (1) Å] and the indolyl-idene ring system [r.m.s. deviation = 0.013 (2) Å] are inclined to one another by 18.52 (6)°. This is similar to the arrangement [16.51 (18)°] found for the N-hy-droxy-ethyl adduct of the title compound [Bhuiyan et al. (2011 ▶). Mol. Cryst. Liq. Cryst. 548, 1-12]. Replacing the hy-droxy-ethyl group with 3,5-di-benzyl-oxybenzoate has not resulted in a non-centrosymmetric lattice arrangement or significant changes to the basic mol-ecular structure. In the crystal, mol-ecules are linked via pairs of C-H⋯N hydrogen bonds, forming inversion dimers with an R (2) 2(20) ring motif. The dimers are linked via C-H⋯O hydrogen bonds, forming C(17) chains along [010]. The chains are linked by further C-H⋯N hydrogen bonds, forming layers parallel to (001) and enclosing R 2 (2)(44) ring motifs. There are also C-H⋯π inter-actions present, stabilizing the inter-layer orientation of the pendant bis-(benz-yloxy)benzo-yloxy group.

Related literature

For general background to organic non-linear optical (NLO) materials and details of similar structures, see: Kim et al. (2007 ▶); Gainsford et al. (2007 ▶, 2008 ▶); Smith et al. (2006 ▶); Bhuiyan et al. (2011 ▶); Li et al. (2005 ▶); Ojala et al. (2012 ▶). For the synthesis of the title compound, see: Clarke et al. (2009 ▶). For details of the N-hy­droxy­ethyl adduct of the title compound, see: Bhuiyan et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For details of the Cambridge Structural Database (CSD), see: Allen (2002 ▶).

Experimental

Crystal data

C48H42N4O5

M = 754.86

Monoclinic,

a = 16.1925 (5) Å

b = 15.6802 (5) Å

c = 17.6529 (6) Å

β = 115.038 (2)°

V = 4060.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 120 K

0.31 × 0.26 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.682, T max = 0.746

106328 measured reflections

14582 independent reflections

9621 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.153

S = 1.02

14582 reflections

518 parameters

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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 Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813032868/su2670sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032868/su2670Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813032868/su2670Isup3.cml

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

C48H42N4O5	F(000) = 1592
Mr = 754.86	Dx = 1.235 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9867 reflections
a = 16.1925 (5) Å	θ = 2.6–31.1°
b = 15.6802 (5) Å	µ = 0.08 mm−1
c = 17.6529 (6) Å	T = 120 K
β = 115.038 (2)°	Block, blue
V = 4060.9 (2) Å3	0.31 × 0.26 × 0.25 mm
Z = 4

Bruker APEXII CCD diffractometer	14582 independent reflections
Radiation source: fine-focus sealed tube	9621 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.049
Detector resolution: 8.333 pixels mm-1	θmax = 32.7°, θmin = 2.6°
φ and ω scans	h = −24→24
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −23→23
Tmin = 0.682, Tmax = 0.746	l = −26→25
106328 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0778P)2 + 0.7163P] where P = (Fo2 + 2Fc2)/3
14582 reflections	(Δ/σ)max = 0.001
518 parameters	Δρmax = 0.48 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Experimental. Spectroscopic and other data for the title compound: 1H NMR (d6-DMSO) δ 1.60 (6H, s, 2xCH3), 1.64 (6H, s, 2xCH3), 4.51 (2H, t, J 5.1 Hz, CH2), 4.65 (2H, t, J 5.1, CH2), 5.02 (4H, s, 2xCH2), 6.01 (1H, d, J 14.2 Hz, CH), 6.32–6.43 (2H, m, 2xCH), 6.86 (1H, t, J 2.3 Hz, ArH), 7.05 (2H, d, J 2.5 Hz, ArH), 7.15 (1 H, t, J 8.0 Hz, ArH), 7.29–7.41 (11H, m, ArH), 7.45 (1H, d, J 8.0 Hz, ArH), 7.54 (1H, d, J 7.6 Hz, ArH), 7.82 (1H, t, J 13.5 Hz, CH), 8.06 (1H, t, J 13.5 Hz, CH). 13C NMR (d6-DMSO) δ 26.8, 27.5, 42.9, 45.9, 48.9, 61.9, 69.9, 95.9, 103.8, 107.5, 108.4, 109.2, 111.2, 113.5, 114.5, 115.3, 122.6, 124.6, 125.9, 127.6, 128.3, 128.8, 131.4, 136.8, 141.0, 142.6, 151.7, 152.8, 159.7, 165.5, 170.8, 172.1, 176.8. MS - Found: MNa+ 777.3050; Calc: 777.3053; Δ = 0.3 p.p.m.; M.p. = 549 K (dec.).

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
O1	0.27488 (6)	0.17454 (5)	0.02308 (5)	0.02415 (17)
O2	0.28317 (6)	0.87522 (5)	0.11107 (6)	0.02664 (18)
O3	0.33004 (7)	1.01185 (6)	0.13326 (7)	0.0354 (2)
O4	0.02801 (6)	1.15735 (5)	0.06642 (6)	0.0315 (2)
O5	−0.00979 (7)	0.87452 (6)	0.14487 (7)	0.0380 (2)
N1	0.36962 (14)	0.09712 (9)	−0.18815 (11)	0.0610 (5)
N2	0.21981 (9)	−0.03146 (8)	−0.07112 (9)	0.0389 (3)
N3	0.46305 (13)	0.29291 (10)	−0.09615 (11)	0.0584 (4)
N4	0.40465 (7)	0.79660 (6)	0.25765 (6)	0.02294 (19)
C1	0.34424 (12)	0.10072 (8)	−0.13685 (10)	0.0375 (3)
C2	0.30870 (9)	0.10250 (7)	−0.07603 (8)	0.0266 (2)
C3	0.25862 (9)	0.02976 (8)	−0.07198 (8)	0.0281 (2)
C4	0.35515 (8)	0.30273 (7)	0.04015 (7)	0.0212 (2)
C5	0.29468 (8)	0.25456 (7)	0.07175 (7)	0.0213 (2)
C6	0.31764 (8)	0.17354 (7)	−0.02671 (7)	0.0221 (2)
C7	0.36677 (9)	0.25051 (7)	−0.01856 (8)	0.0234 (2)
C8	0.34273 (9)	0.22813 (8)	0.16286 (8)	0.0272 (2)
H8A	0.3048	0.1871	0.1757	0.041*
H8B	0.3531	0.2785	0.1986	0.041*
H8C	0.4014	0.2017	0.1731	0.041*
C9	0.20331 (9)	0.29729 (8)	0.04958 (9)	0.0306 (3)
H9A	0.1762	0.3130	−0.0097	0.046*
H9B	0.2120	0.3486	0.0837	0.046*
H9C	0.1626	0.2578	0.0604	0.046*
C10	0.41958 (11)	0.27260 (8)	−0.06229 (9)	0.0337 (3)
C11	0.39111 (9)	0.38450 (7)	0.06261 (7)	0.0236 (2)
H11	0.4262	0.4064	0.0354	0.028*
C12	0.38020 (8)	0.43656 (7)	0.12114 (7)	0.0225 (2)
H12	0.3501	0.4133	0.1524	0.027*
C13	0.41038 (8)	0.52084 (7)	0.13727 (7)	0.0233 (2)
H13	0.4431	0.5446	0.1086	0.028*
C14	0.39374 (8)	0.57040 (7)	0.19393 (7)	0.0229 (2)
H14	0.3681	0.5438	0.2274	0.028*
C15	0.41262 (8)	0.65764 (7)	0.20468 (7)	0.0227 (2)
H15	0.4441	0.6821	0.1752	0.027*
C16	0.38935 (8)	0.71132 (7)	0.25470 (7)	0.0217 (2)
C17	0.34510 (9)	0.68940 (8)	0.31372 (8)	0.0262 (2)
C18	0.33633 (10)	0.77700 (9)	0.34542 (8)	0.0307 (3)
C19	0.29889 (12)	0.80185 (11)	0.39941 (10)	0.0450 (4)
H19	0.2734	0.7609	0.4231	0.054*
C20	0.29939 (14)	0.88811 (12)	0.41813 (11)	0.0526 (4)
H20	0.2745	0.9062	0.4555	0.063*
C21	0.33549 (12)	0.94761 (11)	0.38333 (10)	0.0453 (4)
H21	0.3352	1.0061	0.3973	0.054*
C22	0.37253 (10)	0.92416 (9)	0.32799 (9)	0.0337 (3)
H22	0.3969	0.9652	0.3035	0.040*
C23	0.37188 (9)	0.83781 (8)	0.31062 (8)	0.0265 (2)
C24	0.40886 (10)	0.63264 (9)	0.38589 (8)	0.0343 (3)
H24A	0.4681	0.6608	0.4145	0.052*
H24B	0.4171	0.5777	0.3635	0.052*
H24C	0.3820	0.6233	0.4256	0.052*
C25	0.25050 (10)	0.64853 (9)	0.26807 (9)	0.0343 (3)
H25A	0.2206	0.6455	0.3060	0.051*
H25B	0.2571	0.5909	0.2499	0.051*
H25C	0.2135	0.6831	0.2192	0.051*
C26	0.44046 (8)	0.84259 (7)	0.20598 (8)	0.0241 (2)
H26A	0.4949	0.8123	0.2076	0.029*
H26B	0.4598	0.9003	0.2295	0.029*
C27	0.37088 (9)	0.85040 (7)	0.11610 (8)	0.0259 (2)
H27A	0.3919	0.8933	0.0871	0.031*
H27B	0.3653	0.7950	0.0874	0.031*
C28	0.27154 (9)	0.95937 (7)	0.12110 (8)	0.0266 (2)
C29	0.17925 (8)	0.97655 (7)	0.11620 (8)	0.0258 (2)
C30	0.14390 (9)	1.05744 (7)	0.09358 (8)	0.0270 (2)
H30	0.1778	1.1002	0.0811	0.032*
C31	0.05758 (9)	1.07557 (7)	0.08930 (8)	0.0261 (2)
C32	0.00763 (9)	1.01335 (8)	0.10696 (8)	0.0275 (2)
H32	−0.0511	1.0259	0.1040	0.033*
C33	0.04495 (9)	0.93180 (8)	0.12925 (9)	0.0292 (3)
C34	0.13050 (9)	0.91234 (8)	0.13456 (8)	0.0289 (3)
H34	0.1555	0.8569	0.1502	0.035*
C35	−0.05544 (9)	1.18186 (8)	0.07035 (9)	0.0312 (3)
H35A	−0.0516	1.1714	0.1270	0.037*
H35B	−0.1071	1.1485	0.0297	0.037*
C36	−0.06892 (9)	1.27525 (8)	0.04970 (8)	0.0289 (3)
C37	−0.14460 (10)	1.30486 (9)	−0.01773 (9)	0.0365 (3)
H37	−0.1888	1.2656	−0.0531	0.044*
C38	−0.15680 (12)	1.39206 (10)	−0.03448 (10)	0.0442 (4)
H38	−0.2093	1.4118	−0.0810	0.053*
C39	−0.09368 (13)	1.44910 (10)	0.01558 (12)	0.0481 (4)
H39	−0.1026	1.5085	0.0044	0.058*
C40	−0.01739 (14)	1.42040 (10)	0.08203 (13)	0.0566 (5)
H40	0.0269	1.4600	0.1166	0.068*
C41	−0.00462 (12)	1.33398 (10)	0.09894 (11)	0.0461 (4)
H41	0.0488	1.3147	0.1448	0.055*
C42	0.02282 (11)	0.78935 (8)	0.16259 (10)	0.0371 (3)
H42A	0.0810	0.7882	0.2135	0.045*
H42B	0.0341	0.7665	0.1155	0.045*
C43	−0.04667 (10)	0.73513 (8)	0.17551 (9)	0.0339 (3)
C44	−0.11661 (11)	0.76979 (10)	0.19029 (9)	0.0387 (3)
H44	−0.1233	0.8300	0.1907	0.046*
C45	−0.17766 (12)	0.71686 (12)	0.20469 (10)	0.0495 (4)
H45	−0.2256	0.7410	0.2152	0.059*
C46	−0.16855 (14)	0.62960 (12)	0.20376 (11)	0.0551 (5)
H46	−0.2101	0.5936	0.2138	0.066*
C48	−0.03825 (13)	0.64694 (9)	0.17448 (11)	0.0465 (4)
H48	0.0097	0.6224	0.1642	0.056*
C47	−0.09962 (15)	0.59470 (11)	0.18843 (11)	0.0578 (5)
H47	−0.0938	0.5345	0.1873	0.069*

	U11	U22	U33	U12	U13	U23
O1	0.0326 (5)	0.0186 (3)	0.0293 (4)	−0.0060 (3)	0.0209 (4)	−0.0063 (3)
O2	0.0267 (4)	0.0188 (4)	0.0355 (5)	0.0004 (3)	0.0142 (4)	0.0002 (3)
O3	0.0307 (5)	0.0218 (4)	0.0535 (6)	−0.0023 (4)	0.0177 (5)	0.0007 (4)
O4	0.0326 (5)	0.0187 (4)	0.0493 (6)	0.0035 (3)	0.0231 (4)	0.0048 (4)
O5	0.0388 (6)	0.0226 (4)	0.0617 (7)	0.0014 (4)	0.0303 (5)	0.0103 (4)
N1	0.1162 (15)	0.0314 (6)	0.0732 (10)	−0.0188 (8)	0.0769 (11)	−0.0161 (6)
N2	0.0481 (7)	0.0293 (5)	0.0517 (7)	−0.0109 (5)	0.0333 (6)	−0.0112 (5)
N3	0.0851 (12)	0.0507 (8)	0.0711 (10)	−0.0260 (8)	0.0638 (10)	−0.0172 (7)
N4	0.0282 (5)	0.0182 (4)	0.0264 (5)	−0.0009 (4)	0.0153 (4)	−0.0028 (3)
C1	0.0633 (10)	0.0191 (5)	0.0462 (8)	−0.0076 (6)	0.0387 (8)	−0.0077 (5)
C2	0.0367 (7)	0.0200 (5)	0.0317 (6)	−0.0033 (4)	0.0228 (5)	−0.0039 (4)
C3	0.0359 (7)	0.0235 (5)	0.0322 (6)	−0.0024 (5)	0.0215 (5)	−0.0065 (5)
C4	0.0265 (5)	0.0167 (4)	0.0234 (5)	−0.0004 (4)	0.0133 (4)	0.0010 (4)
C5	0.0277 (6)	0.0163 (4)	0.0244 (5)	−0.0029 (4)	0.0155 (5)	−0.0036 (4)
C6	0.0278 (6)	0.0184 (5)	0.0246 (5)	−0.0010 (4)	0.0155 (5)	−0.0004 (4)
C7	0.0311 (6)	0.0184 (5)	0.0276 (6)	−0.0031 (4)	0.0189 (5)	−0.0021 (4)
C8	0.0351 (7)	0.0226 (5)	0.0262 (6)	−0.0049 (5)	0.0152 (5)	−0.0004 (4)
C9	0.0284 (6)	0.0270 (6)	0.0394 (7)	−0.0004 (5)	0.0172 (6)	−0.0067 (5)
C10	0.0480 (8)	0.0256 (6)	0.0402 (7)	−0.0083 (5)	0.0311 (7)	−0.0070 (5)
C11	0.0306 (6)	0.0180 (5)	0.0264 (5)	−0.0019 (4)	0.0162 (5)	0.0008 (4)
C12	0.0273 (6)	0.0172 (5)	0.0244 (5)	−0.0009 (4)	0.0123 (5)	0.0013 (4)
C13	0.0289 (6)	0.0169 (5)	0.0263 (5)	−0.0008 (4)	0.0139 (5)	0.0008 (4)
C14	0.0264 (6)	0.0182 (5)	0.0252 (5)	−0.0009 (4)	0.0120 (5)	0.0015 (4)
C15	0.0277 (6)	0.0172 (5)	0.0271 (6)	−0.0020 (4)	0.0154 (5)	−0.0007 (4)
C16	0.0245 (5)	0.0184 (5)	0.0241 (5)	−0.0011 (4)	0.0122 (4)	−0.0004 (4)
C17	0.0308 (6)	0.0268 (5)	0.0253 (6)	−0.0018 (5)	0.0161 (5)	0.0006 (4)
C18	0.0349 (7)	0.0341 (6)	0.0284 (6)	0.0024 (5)	0.0186 (5)	−0.0029 (5)
C19	0.0545 (10)	0.0544 (9)	0.0395 (8)	0.0036 (8)	0.0328 (8)	−0.0041 (7)
C20	0.0636 (11)	0.0609 (11)	0.0450 (9)	0.0115 (9)	0.0343 (9)	−0.0126 (8)
C21	0.0510 (9)	0.0424 (8)	0.0415 (8)	0.0117 (7)	0.0184 (7)	−0.0148 (7)
C22	0.0363 (7)	0.0274 (6)	0.0353 (7)	0.0034 (5)	0.0130 (6)	−0.0089 (5)
C23	0.0282 (6)	0.0264 (5)	0.0261 (6)	0.0028 (5)	0.0126 (5)	−0.0055 (4)
C24	0.0419 (8)	0.0343 (7)	0.0269 (6)	−0.0010 (6)	0.0146 (6)	0.0046 (5)
C25	0.0316 (7)	0.0403 (7)	0.0361 (7)	−0.0061 (6)	0.0194 (6)	−0.0007 (6)
C26	0.0266 (6)	0.0174 (5)	0.0319 (6)	−0.0024 (4)	0.0160 (5)	−0.0005 (4)
C27	0.0304 (6)	0.0211 (5)	0.0312 (6)	0.0016 (4)	0.0180 (5)	0.0015 (4)
C28	0.0289 (6)	0.0189 (5)	0.0314 (6)	0.0007 (4)	0.0121 (5)	0.0021 (4)
C29	0.0268 (6)	0.0209 (5)	0.0303 (6)	−0.0012 (4)	0.0128 (5)	−0.0005 (4)
C30	0.0282 (6)	0.0196 (5)	0.0346 (6)	−0.0022 (4)	0.0147 (5)	−0.0004 (4)
C31	0.0309 (6)	0.0174 (5)	0.0319 (6)	0.0004 (4)	0.0150 (5)	0.0001 (4)
C32	0.0284 (6)	0.0225 (5)	0.0350 (6)	−0.0001 (4)	0.0169 (5)	0.0003 (5)
C33	0.0339 (7)	0.0212 (5)	0.0372 (7)	−0.0014 (5)	0.0194 (6)	0.0024 (5)
C34	0.0311 (6)	0.0199 (5)	0.0372 (7)	0.0006 (4)	0.0159 (5)	0.0037 (5)
C35	0.0332 (7)	0.0242 (5)	0.0424 (7)	0.0034 (5)	0.0220 (6)	0.0025 (5)
C36	0.0329 (6)	0.0235 (5)	0.0344 (6)	0.0043 (5)	0.0183 (5)	0.0020 (5)
C37	0.0329 (7)	0.0334 (7)	0.0404 (8)	0.0036 (5)	0.0127 (6)	−0.0024 (6)
C38	0.0465 (9)	0.0405 (8)	0.0414 (8)	0.0166 (7)	0.0144 (7)	0.0096 (6)
C39	0.0593 (10)	0.0267 (7)	0.0609 (10)	0.0097 (7)	0.0279 (9)	0.0078 (7)
C40	0.0586 (11)	0.0271 (7)	0.0676 (12)	−0.0023 (7)	0.0107 (9)	−0.0053 (7)
C41	0.0470 (9)	0.0297 (7)	0.0457 (9)	0.0046 (6)	0.0043 (7)	0.0008 (6)
C42	0.0417 (8)	0.0227 (6)	0.0523 (9)	0.0014 (5)	0.0252 (7)	0.0075 (6)
C43	0.0406 (8)	0.0279 (6)	0.0305 (6)	−0.0057 (5)	0.0123 (6)	0.0057 (5)
C44	0.0418 (8)	0.0366 (7)	0.0378 (7)	−0.0072 (6)	0.0169 (6)	0.0064 (6)
C45	0.0461 (9)	0.0617 (10)	0.0408 (8)	−0.0168 (8)	0.0184 (7)	0.0074 (7)
C46	0.0626 (12)	0.0576 (10)	0.0387 (8)	−0.0318 (9)	0.0154 (8)	0.0090 (7)
C48	0.0629 (11)	0.0283 (7)	0.0469 (9)	−0.0062 (7)	0.0220 (8)	0.0048 (6)
C47	0.0840 (14)	0.0348 (8)	0.0465 (10)	−0.0225 (9)	0.0198 (10)	0.0067 (7)

O1—C6	1.3294 (13)	C21—H21	0.9500
O1—C5	1.4772 (13)	C22—C23	1.3873 (17)
O2—C28	1.3550 (14)	C22—H22	0.9500
O2—C27	1.4387 (15)	C24—H24A	0.9800
O3—C28	1.2036 (15)	C24—H24B	0.9800
O4—C31	1.3686 (14)	C24—H24C	0.9800
O4—C35	1.4344 (16)	C25—H25A	0.9800
O5—C33	1.3694 (15)	C25—H25B	0.9800
O5—C42	1.4215 (15)	C25—H25C	0.9800
N1—C1	1.1433 (18)	C26—C27	1.5128 (18)
N2—C3	1.1510 (16)	C26—H26A	0.9900
N3—C10	1.1446 (18)	C26—H26B	0.9900
N4—C16	1.3570 (14)	C27—H27A	0.9900
N4—C23	1.4119 (15)	C27—H27B	0.9900
N4—C26	1.4615 (15)	C28—C29	1.4845 (18)
C1—C2	1.4170 (17)	C29—C30	1.3793 (17)
C2—C6	1.3830 (16)	C29—C34	1.3994 (17)
C2—C3	1.4187 (17)	C30—C31	1.3968 (18)
C4—C11	1.3945 (15)	C30—H30	0.9500
C4—C7	1.3947 (15)	C31—C32	1.3843 (17)
C4—C5	1.5173 (15)	C32—C33	1.3979 (17)
C5—C9	1.5170 (17)	C32—H32	0.9500
C5—C8	1.5182 (17)	C33—C34	1.3823 (18)
C6—C7	1.4190 (15)	C34—H34	0.9500
C7—C10	1.4162 (17)	C35—C36	1.5025 (17)
C8—H8A	0.9800	C35—H35A	0.9900
C8—H8B	0.9800	C35—H35B	0.9900
C8—H8C	0.9800	C36—C37	1.378 (2)
C9—H9A	0.9800	C36—C41	1.386 (2)
C9—H9B	0.9800	C37—C38	1.395 (2)
C9—H9C	0.9800	C37—H37	0.9500
C11—C12	1.3854 (16)	C38—C39	1.364 (3)
C11—H11	0.9500	C38—H38	0.9500
C12—C13	1.3959 (15)	C39—C40	1.370 (3)
C12—H12	0.9500	C39—H39	0.9500
C13—C14	1.3801 (16)	C40—C41	1.384 (2)
C13—H13	0.9500	C40—H40	0.9500
C14—C15	1.3969 (15)	C41—H41	0.9500
C14—H14	0.9500	C42—C43	1.5027 (19)
C15—C16	1.3826 (15)	C42—H42A	0.9900
C15—H15	0.9500	C42—H42B	0.9900
C16—C17	1.5328 (16)	C43—C44	1.377 (2)
C17—C18	1.5124 (18)	C43—C48	1.391 (2)
C17—C25	1.5367 (19)	C44—C45	1.394 (2)
C17—C24	1.5387 (18)	C44—H44	0.9500
C18—C19	1.3845 (19)	C45—C46	1.377 (3)
C18—C23	1.3846 (19)	C45—H45	0.9500
C19—C20	1.392 (2)	C46—C47	1.369 (3)
C19—H19	0.9500	C46—H46	0.9500
C20—C21	1.376 (3)	C48—C47	1.388 (2)
C20—H20	0.9500	C48—H48	0.9500
C21—C22	1.395 (2)	C47—H47	0.9500
C6—O1—C5	110.42 (8)	C17—C25—H25A	109.5
C28—O2—C27	116.33 (9)	C17—C25—H25B	109.5
C31—O4—C35	117.11 (10)	H25A—C25—H25B	109.5
C33—O5—C42	116.65 (11)	C17—C25—H25C	109.5
C16—N4—C23	111.27 (10)	H25A—C25—H25C	109.5
C16—N4—C26	125.20 (9)	H25B—C25—H25C	109.5
C23—N4—C26	123.17 (9)	N4—C26—C27	112.24 (10)
N1—C1—C2	176.93 (18)	N4—C26—H26A	109.2
C6—C2—C1	121.67 (11)	C27—C26—H26A	109.2
C6—C2—C3	121.70 (11)	N4—C26—H26B	109.2
C1—C2—C3	116.52 (11)	C27—C26—H26B	109.2
N2—C3—C2	176.49 (13)	H26A—C26—H26B	107.9
C11—C4—C7	125.42 (10)	O2—C27—C26	111.36 (10)
C11—C4—C5	127.58 (10)	O2—C27—H27A	109.4
C7—C4—C5	106.97 (9)	C26—C27—H27A	109.4
O1—C5—C9	106.09 (9)	O2—C27—H27B	109.4
O1—C5—C4	102.95 (8)	C26—C27—H27B	109.4
C9—C5—C4	113.33 (10)	H27A—C27—H27B	108.0
O1—C5—C8	105.78 (9)	O3—C28—O2	123.14 (12)
C9—C5—C8	113.60 (10)	O3—C28—C29	125.68 (11)
C4—C5—C8	113.84 (10)	O2—C28—C29	111.18 (10)
O1—C6—C2	118.73 (10)	C30—C29—C34	121.53 (12)
O1—C6—C7	110.45 (9)	C30—C29—C28	117.90 (11)
C2—C6—C7	130.82 (11)	C34—C29—C28	120.57 (11)
C4—C7—C10	124.33 (11)	C29—C30—C31	119.08 (11)
C4—C7—C6	109.18 (10)	C29—C30—H30	120.5
C10—C7—C6	126.50 (11)	C31—C30—H30	120.5
C5—C8—H8A	109.5	O4—C31—C32	124.20 (11)
C5—C8—H8B	109.5	O4—C31—C30	115.07 (10)
H8A—C8—H8B	109.5	C32—C31—C30	120.73 (11)
C5—C8—H8C	109.5	C31—C32—C33	118.94 (12)
H8A—C8—H8C	109.5	C31—C32—H32	120.5
H8B—C8—H8C	109.5	C33—C32—H32	120.5
C5—C9—H9A	109.5	O5—C33—C34	123.86 (11)
C5—C9—H9B	109.5	O5—C33—C32	114.65 (11)
H9A—C9—H9B	109.5	C34—C33—C32	121.49 (11)
C5—C9—H9C	109.5	C33—C34—C29	118.22 (11)
H9A—C9—H9C	109.5	C33—C34—H34	120.9
H9B—C9—H9C	109.5	C29—C34—H34	120.9
N3—C10—C7	177.74 (15)	O4—C35—C36	107.01 (10)
C12—C11—C4	125.74 (11)	O4—C35—H35A	110.3
C12—C11—H11	117.1	C36—C35—H35A	110.3
C4—C11—H11	117.1	O4—C35—H35B	110.3
C11—C12—C13	124.47 (11)	C36—C35—H35B	110.3
C11—C12—H12	117.8	H35A—C35—H35B	108.6
C13—C12—H12	117.8	C37—C36—C41	118.36 (13)
C14—C13—C12	121.48 (11)	C37—C36—C35	121.51 (13)
C14—C13—H13	119.3	C41—C36—C35	120.13 (13)
C12—C13—H13	119.3	C36—C37—C38	120.50 (14)
C13—C14—C15	123.46 (11)	C36—C37—H37	119.8
C13—C14—H14	118.3	C38—C37—H37	119.8
C15—C14—H14	118.3	C39—C38—C37	120.35 (15)
C16—C15—C14	125.44 (11)	C39—C38—H38	119.8
C16—C15—H15	117.3	C37—C38—H38	119.8
C14—C15—H15	117.3	C38—C39—C40	119.74 (14)
N4—C16—C15	121.99 (10)	C38—C39—H39	120.1
N4—C16—C17	108.97 (9)	C40—C39—H39	120.1
C15—C16—C17	129.03 (10)	C39—C40—C41	120.29 (16)
C18—C17—C16	101.06 (9)	C39—C40—H40	119.9
C18—C17—C25	110.12 (11)	C41—C40—H40	119.9
C16—C17—C25	112.71 (10)	C40—C41—C36	120.74 (15)
C18—C17—C24	110.74 (11)	C40—C41—H41	119.6
C16—C17—C24	110.46 (11)	C36—C41—H41	119.6
C25—C17—C24	111.32 (11)	O5—C42—C43	109.42 (12)
C19—C18—C23	119.80 (13)	O5—C42—H42A	109.8
C19—C18—C17	130.34 (13)	C43—C42—H42A	109.8
C23—C18—C17	109.85 (10)	O5—C42—H42B	109.8
C18—C19—C20	118.48 (15)	C43—C42—H42B	109.8
C18—C19—H19	120.8	H42A—C42—H42B	108.2
C20—C19—H19	120.8	C44—C43—C48	119.21 (14)
C21—C20—C19	120.91 (14)	C44—C43—C42	122.29 (13)
C21—C20—H20	119.5	C48—C43—C42	118.48 (14)
C19—C20—H20	119.5	C43—C44—C45	120.21 (15)
C20—C21—C22	121.59 (14)	C43—C44—H44	119.9
C20—C21—H21	119.2	C45—C44—H44	119.9
C22—C21—H21	119.2	C46—C45—C44	120.10 (18)
C23—C22—C21	116.54 (14)	C46—C45—H45	119.9
C23—C22—H22	121.7	C44—C45—H45	119.9
C21—C22—H22	121.7	C47—C46—C45	120.00 (16)
C18—C23—C22	122.67 (12)	C47—C46—H46	120.0
C18—C23—N4	108.78 (10)	C45—C46—H46	120.0
C22—C23—N4	128.55 (12)	C47—C48—C43	120.21 (18)
C17—C24—H24A	109.5	C47—C48—H48	119.9
C17—C24—H24B	109.5	C43—C48—H48	119.9
H24A—C24—H24B	109.5	C46—C47—C48	120.27 (17)
C17—C24—H24C	109.5	C46—C47—H47	119.9
H24A—C24—H24C	109.5	C48—C47—H47	119.9
H24B—C24—H24C	109.5
C6—O1—C5—C9	120.87 (11)	C17—C18—C23—N4	−0.33 (15)
C6—O1—C5—C4	1.58 (12)	C21—C22—C23—C18	0.3 (2)
C6—O1—C5—C8	−118.16 (10)	C21—C22—C23—N4	−179.88 (13)
C11—C4—C5—O1	177.18 (11)	C16—N4—C23—C18	1.80 (14)
C7—C4—C5—O1	−1.19 (12)	C26—N4—C23—C18	175.25 (11)
C11—C4—C5—C9	63.04 (16)	C16—N4—C23—C22	−178.07 (13)
C7—C4—C5—C9	−115.32 (11)	C26—N4—C23—C22	−4.6 (2)
C11—C4—C5—C8	−68.82 (15)	C16—N4—C26—C27	72.97 (14)
C7—C4—C5—C8	112.81 (11)	C23—N4—C26—C27	−99.56 (13)
C5—O1—C6—C2	178.65 (11)	C28—O2—C27—C26	80.57 (12)
C5—O1—C6—C7	−1.38 (13)	N4—C26—C27—O2	45.16 (12)
C1—C2—C6—O1	173.19 (13)	C27—O2—C28—O3	0.31 (18)
C3—C2—C6—O1	−2.79 (19)	C27—O2—C28—C29	−178.92 (10)
C1—C2—C6—C7	−6.8 (2)	O3—C28—C29—C30	24.9 (2)
C3—C2—C6—C7	177.25 (13)	O2—C28—C29—C30	−155.89 (11)
C11—C4—C7—C10	1.9 (2)	O3—C28—C29—C34	−154.74 (14)
C5—C4—C7—C10	−179.64 (13)	O2—C28—C29—C34	24.47 (17)
C11—C4—C7—C6	−177.95 (12)	C34—C29—C30—C31	0.28 (19)
C5—C4—C7—C6	0.46 (14)	C28—C29—C30—C31	−179.36 (11)
O1—C6—C7—C4	0.56 (14)	C35—O4—C31—C32	7.28 (18)
C2—C6—C7—C4	−179.47 (13)	C35—O4—C31—C30	−173.09 (11)
O1—C6—C7—C10	−179.33 (13)	C29—C30—C31—O4	179.96 (11)
C2—C6—C7—C10	0.6 (2)	C29—C30—C31—C32	−0.39 (19)
C7—C4—C11—C12	−179.67 (12)	O4—C31—C32—C33	179.65 (12)
C5—C4—C11—C12	2.2 (2)	C30—C31—C32—C33	0.03 (19)
C4—C11—C12—C13	−174.28 (12)	C42—O5—C33—C34	−3.8 (2)
C11—C12—C13—C14	177.11 (12)	C42—O5—C33—C32	176.13 (12)
C12—C13—C14—C15	−171.91 (12)	C31—C32—C33—O5	−179.50 (12)
C13—C14—C15—C16	173.53 (12)	C31—C32—C33—C34	0.5 (2)
C23—N4—C16—C15	177.74 (11)	O5—C33—C34—C29	179.39 (12)
C26—N4—C16—C15	4.45 (18)	C32—C33—C34—C29	−0.6 (2)
C23—N4—C16—C17	−2.48 (14)	C30—C29—C34—C33	0.2 (2)
C26—N4—C16—C17	−175.77 (11)	C28—C29—C34—C33	179.82 (12)
C14—C15—C16—N4	−175.51 (12)	C31—O4—C35—C36	175.24 (11)
C14—C15—C16—C17	4.8 (2)	O4—C35—C36—C37	119.95 (14)
N4—C16—C17—C18	2.10 (13)	O4—C35—C36—C41	−60.16 (17)
C15—C16—C17—C18	−178.15 (12)	C41—C36—C37—C38	−1.5 (2)
N4—C16—C17—C25	119.60 (12)	C35—C36—C37—C38	178.39 (14)
C15—C16—C17—C25	−60.65 (17)	C36—C37—C38—C39	0.3 (2)
N4—C16—C17—C24	−115.17 (11)	C37—C38—C39—C40	0.8 (3)
C15—C16—C17—C24	64.58 (16)	C38—C39—C40—C41	−0.6 (3)
C16—C17—C18—C19	177.87 (16)	C39—C40—C41—C36	−0.7 (3)
C25—C17—C18—C19	58.5 (2)	C37—C36—C41—C40	1.7 (3)
C24—C17—C18—C19	−65.1 (2)	C35—C36—C41—C40	−178.20 (17)
C16—C17—C18—C23	−1.03 (14)	C33—O5—C42—C43	−178.33 (12)
C25—C17—C18—C23	−120.40 (12)	O5—C42—C43—C44	−16.2 (2)
C24—C17—C18—C23	116.04 (12)	O5—C42—C43—C48	165.43 (14)
C23—C18—C19—C20	−0.9 (2)	C48—C43—C44—C45	0.5 (2)
C17—C18—C19—C20	−179.73 (16)	C42—C43—C44—C45	−177.84 (14)
C18—C19—C20—C21	0.6 (3)	C43—C44—C45—C46	−0.3 (2)
C19—C20—C21—C22	0.2 (3)	C44—C45—C46—C47	−0.2 (3)
C20—C21—C22—C23	−0.6 (2)	C44—C43—C48—C47	−0.2 (2)
C19—C18—C23—C22	0.5 (2)	C42—C43—C48—C47	178.25 (15)
C17—C18—C23—C22	179.55 (12)	C45—C46—C47—C48	0.5 (3)
C19—C18—C23—N4	−179.36 (13)	C43—C48—C47—C46	−0.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···N3i	0.95	2.48	3.404 (2)	165
C30—H30···O1ii	0.95	2.50	3.4136 (17)	162
C32—H32···N2iii	0.95	2.54	3.475 (2)	167
C9—H9A···Cg1iii	0.98	2.89	3.8454 (16)	166

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C29–C34 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯N3i	0.95	2.48	3.404 (2)	165
C30—H30⋯O1ii	0.95	2.50	3.4136 (17)	162
C32—H32⋯N2iii	0.95	2.54	3.475 (2)	167
C9—H9A⋯Cg1iii	0.98	2.89	3.8454 (16)	166

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