Study of naphtho­pyran derivatives: structure and photochromic properties in solution and in polymer film

Four naphtho­pyran derivatives, namely, 3,3-bis­(naphthalen-1-yl)-3H-naphtho­[2,1-b]pyran, C₃₃H₂₂O, NP1, 3,3-bis­([1,1′-biphen­yl]-4-yl)-3H-naphtho­[2,1-b]pyran, C₃₇H₂₆O, NP2, 3,3-bis­(4-phen­oxy­phen­yl)-3H-naphtho­[2,1-b]pyran, C₃₇H₂₆O₂, NP3, and 3,3-bis­(4-meth­oxy-2-methyl­phen­yl)-3H-naphtho­[2,1-b]pyran, C₂₉H₂₆O₃, NP4, were synthesized and their photochromic properties investigated. NP1–NP4 exhibited good photochromism in different solutions and in poly(methyl methacrylate) (PMMA) film under UV light irradiation. Solvatochromism and the electronic and steric effects of the substituent group on photochromism were analyzed and decolouration curves were found to fit a monoexponential kinetic decay in most cases. Single-crystal X-ray analysis of NP1 and NP2 revealed the structure–property relationships. Good fatigue resistance of NP1, both in solution and in the PMMA film, endows it with potential value for applications.

Computing details

For both structures, data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

3,3-Bis(naphthalen-1-yl)-3H-naphtho[2,1-b]pyran (NP1)

Crystal data

C33H22O	Z = 2
Mr = 434.50	F(000) = 456
Triclinic, P1	Dx = 1.299 Mg m^−3
a = 9.990 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.700 (4) Å	Cell parameters from 3784 reflections
c = 11.016 (4) Å	θ = 1.9–27.9°
α = 80.865 (16)°	µ = 0.08 mm^−1
β = 73.669 (19)°	T = 113 K
γ = 82.30 (2)°	Prism, colorless
V = 1110.7 (7) Å^3	0.2 × 0.18 × 0.12 mm

Data collection

Bruker P4 diffractometer	Rint = 0.037
Graphite monochromator	θmax = 27.9°, θmin = 1.9°
ω scans	h = −13→13
14345 measured reflections	k = −14→14
5265 independent reflections	l = −14→13
3003 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.093	w = 1/[σ^2(Fo^2) + (0.036P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
5265 reflections	Δρmax = 0.20 e Å^−3
307 parameters	Δρmin = −0.25 e Å^−3
0 restraints

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.34645 (9)	0.02238 (8)	0.64786 (8)	0.0244 (2)
C1	0.34504 (13)	−0.09959 (13)	0.71123 (12)	0.0226 (3)
C2	0.46659 (14)	−0.18144 (13)	0.67514 (12)	0.0274 (3)
H2	0.545402	−0.152334	0.610640	0.033*
C3	0.47059 (14)	−0.30444 (14)	0.73413 (12)	0.0310 (3)
H3	0.552701	−0.360568	0.709257	0.037*
C4	0.35489 (15)	−0.34924 (13)	0.83119 (12)	0.0287 (3)
C5	0.36184 (16)	−0.47342 (14)	0.89932 (13)	0.0380 (4)
H5	0.444743	−0.529277	0.877259	0.046*
C6	0.25090 (17)	−0.51346 (15)	0.99606 (14)	0.0413 (4)
H6	0.257642	−0.596123	1.041824	0.050*
C7	0.12664 (16)	−0.43239 (15)	1.02800 (13)	0.0367 (4)
H7	0.049488	−0.461352	1.094636	0.044*
C8	0.11543 (15)	−0.31210 (14)	0.96420 (12)	0.0305 (3)
H8	0.030360	−0.258986	0.986241	0.037*
C9	0.23044 (14)	−0.26635 (13)	0.86518 (12)	0.0253 (3)
C10	0.22665 (13)	−0.13848 (13)	0.80243 (11)	0.0230 (3)
C11	0.10652 (14)	−0.04388 (14)	0.82946 (12)	0.0266 (3)
H11	0.015961	−0.069668	0.872229	0.032*
C12	0.12436 (13)	0.07832 (13)	0.79402 (11)	0.0247 (3)
H12	0.046030	0.140041	0.811375	0.030*
C13	0.26847 (13)	0.12078 (12)	0.72603 (11)	0.0228 (3)
C14	0.25041 (13)	0.24239 (13)	0.63495 (11)	0.0227 (3)
C15	0.27885 (14)	0.35496 (13)	0.66102 (13)	0.0303 (3)
H15	0.314689	0.354704	0.732336	0.036*
C16	0.25713 (15)	0.47135 (14)	0.58634 (14)	0.0378 (4)
H16	0.280399	0.547621	0.606030	0.045*
C17	0.20258 (15)	0.47408 (14)	0.48567 (14)	0.0361 (4)
H17	0.188058	0.552615	0.435009	0.043*
C18	0.16744 (13)	0.36138 (13)	0.45591 (12)	0.0267 (3)
C19	0.10681 (14)	0.36565 (14)	0.35273 (13)	0.0336 (4)
H19	0.090748	0.445018	0.303975	0.040*
C20	0.07146 (14)	0.25861 (14)	0.32256 (12)	0.0333 (4)
H20	0.030438	0.263352	0.253724	0.040*
C21	0.09577 (13)	0.14112 (14)	0.39340 (12)	0.0294 (3)
H21	0.071792	0.066154	0.371708	0.035*
C22	0.15383 (13)	0.13302 (13)	0.49381 (11)	0.0247 (3)
H22	0.169338	0.052317	0.540545	0.030*
C23	0.19118 (12)	0.24277 (13)	0.52924 (11)	0.0225 (3)
C24	0.35350 (13)	0.13590 (12)	0.81882 (11)	0.0212 (3)
C25	0.29169 (13)	0.12767 (12)	0.94734 (12)	0.0252 (3)
H25	0.195939	0.111607	0.978045	0.030*
C26	0.36505 (14)	0.14219 (13)	1.03564 (12)	0.0279 (3)
H26	0.318728	0.136780	1.124083	0.033*
C27	0.50221 (14)	0.16392 (13)	0.99356 (12)	0.0269 (3)
H27	0.551450	0.173882	1.053170	0.032*
C28	0.57292 (13)	0.17197 (12)	0.86247 (12)	0.0225 (3)
C29	0.71709 (14)	0.19284 (13)	0.81836 (13)	0.0301 (3)
H29	0.766421	0.202006	0.878165	0.036*
C30	0.78611 (14)	0.19998 (13)	0.69215 (13)	0.0311 (3)
H30	0.882828	0.212933	0.664827	0.037*
C31	0.71406 (14)	0.18818 (13)	0.60234 (12)	0.0286 (3)
H31	0.762039	0.194343	0.514237	0.034*
C32	0.57538 (13)	0.16787 (13)	0.64116 (12)	0.0254 (3)
H32	0.528380	0.160328	0.579097	0.030*
C33	0.49947 (13)	0.15773 (12)	0.77225 (11)	0.0209 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0239 (5)	0.0275 (5)	0.0223 (5)	−0.0005 (4)	−0.0067 (4)	−0.0054 (4)
C1	0.0247 (7)	0.0253 (8)	0.0215 (7)	−0.0008 (6)	−0.0115 (6)	−0.0058 (6)
C2	0.0235 (7)	0.0378 (9)	0.0229 (7)	−0.0005 (6)	−0.0066 (6)	−0.0109 (6)
C3	0.0292 (8)	0.0355 (9)	0.0316 (8)	0.0079 (7)	−0.0117 (7)	−0.0162 (7)
C4	0.0377 (9)	0.0282 (8)	0.0260 (8)	−0.0046 (7)	−0.0152 (7)	−0.0070 (6)
C5	0.0493 (10)	0.0298 (9)	0.0431 (9)	0.0021 (7)	−0.0239 (8)	−0.0121 (7)
C6	0.0618 (11)	0.0285 (9)	0.0413 (10)	−0.0126 (8)	−0.0257 (9)	0.0017 (7)
C7	0.0458 (10)	0.0386 (10)	0.0325 (8)	−0.0177 (8)	−0.0184 (7)	0.0015 (7)
C8	0.0354 (9)	0.0334 (9)	0.0283 (8)	−0.0115 (7)	−0.0148 (7)	−0.0021 (7)
C9	0.0293 (8)	0.0288 (8)	0.0239 (7)	−0.0041 (6)	−0.0145 (6)	−0.0067 (6)
C10	0.0229 (7)	0.0300 (8)	0.0193 (7)	−0.0055 (6)	−0.0087 (6)	−0.0044 (6)
C11	0.0192 (7)	0.0387 (9)	0.0231 (7)	−0.0020 (6)	−0.0063 (6)	−0.0069 (6)
C12	0.0215 (7)	0.0311 (8)	0.0221 (7)	−0.0009 (6)	−0.0081 (6)	−0.0025 (6)
C13	0.0229 (7)	0.0259 (8)	0.0211 (7)	0.0008 (6)	−0.0075 (6)	−0.0067 (6)
C14	0.0186 (7)	0.0273 (8)	0.0220 (7)	−0.0002 (6)	−0.0064 (5)	−0.0025 (6)
C15	0.0322 (8)	0.0322 (9)	0.0312 (8)	0.0009 (6)	−0.0163 (6)	−0.0067 (7)
C16	0.0479 (10)	0.0259 (8)	0.0461 (9)	−0.0006 (7)	−0.0234 (8)	−0.0060 (7)
C17	0.0438 (9)	0.0277 (9)	0.0381 (9)	0.0021 (7)	−0.0177 (7)	−0.0002 (7)
C18	0.0239 (7)	0.0323 (8)	0.0220 (7)	0.0014 (6)	−0.0059 (6)	−0.0016 (6)
C19	0.0361 (9)	0.0368 (9)	0.0267 (8)	0.0041 (7)	−0.0126 (7)	0.0014 (7)
C20	0.0325 (8)	0.0463 (10)	0.0234 (8)	−0.0009 (7)	−0.0124 (6)	−0.0042 (7)
C21	0.0255 (8)	0.0392 (9)	0.0260 (8)	−0.0075 (7)	−0.0079 (6)	−0.0059 (7)
C22	0.0200 (7)	0.0300 (8)	0.0233 (7)	−0.0038 (6)	−0.0050 (6)	−0.0014 (6)
C23	0.0155 (7)	0.0305 (8)	0.0201 (7)	−0.0006 (5)	−0.0026 (5)	−0.0040 (6)
C24	0.0208 (7)	0.0231 (7)	0.0208 (7)	0.0009 (5)	−0.0080 (5)	−0.0041 (6)
C25	0.0198 (7)	0.0298 (8)	0.0247 (7)	0.0013 (6)	−0.0047 (6)	−0.0054 (6)
C26	0.0332 (8)	0.0304 (8)	0.0194 (7)	0.0047 (6)	−0.0076 (6)	−0.0066 (6)
C27	0.0324 (8)	0.0281 (8)	0.0257 (8)	0.0017 (6)	−0.0159 (6)	−0.0081 (6)
C28	0.0244 (7)	0.0194 (7)	0.0258 (7)	0.0002 (6)	−0.0105 (6)	−0.0040 (6)
C29	0.0292 (8)	0.0310 (8)	0.0367 (9)	−0.0036 (6)	−0.0186 (7)	−0.0055 (7)
C30	0.0215 (7)	0.0334 (9)	0.0393 (9)	−0.0077 (6)	−0.0084 (7)	−0.0019 (7)
C31	0.0267 (8)	0.0303 (8)	0.0271 (8)	−0.0043 (6)	−0.0045 (6)	−0.0016 (6)
C32	0.0260 (7)	0.0284 (8)	0.0239 (7)	−0.0031 (6)	−0.0095 (6)	−0.0036 (6)
C33	0.0227 (7)	0.0193 (7)	0.0223 (7)	−0.0001 (5)	−0.0090 (6)	−0.0037 (5)

Geometric parameters (Å, º)

O1—C1	1.3787 (16)	C16—C17	1.3613 (18)
O1—C13	1.4655 (15)	C17—H17	0.9500
C1—C2	1.3977 (18)	C17—C18	1.4102 (19)
C1—C10	1.3828 (17)	C18—C19	1.4227 (17)
C2—H2	0.9500	C18—C23	1.4216 (18)
C2—C3	1.3730 (19)	C19—H19	0.9500
C3—H3	0.9500	C19—C20	1.3573 (19)
C3—C4	1.4140 (18)	C20—H20	0.9500
C4—C5	1.4218 (19)	C20—C21	1.4005 (19)
C4—C9	1.4215 (19)	C21—H21	0.9500
C5—H5	0.9500	C21—C22	1.3727 (17)
C5—C6	1.366 (2)	C22—H22	0.9500
C6—H6	0.9500	C22—C23	1.4197 (18)
C6—C7	1.407 (2)	C24—C25	1.3699 (17)
C7—H7	0.9500	C24—C33	1.4410 (17)
C7—C8	1.372 (2)	C25—H25	0.9500
C8—H8	0.9500	C25—C26	1.4096 (17)
C8—C9	1.4233 (18)	C26—H26	0.9500
C9—C10	1.4324 (19)	C26—C27	1.3566 (18)
C10—C11	1.4570 (19)	C27—H27	0.9500
C11—H11	0.9500	C27—C28	1.4124 (18)
C11—C12	1.3247 (19)	C28—C29	1.4208 (18)
C12—H12	0.9500	C28—C33	1.4274 (16)
C12—C13	1.5168 (17)	C29—H29	0.9500
C13—C14	1.5352 (18)	C29—C30	1.3622 (18)
C13—C24	1.5396 (16)	C30—H30	0.9500
C14—C15	1.3644 (18)	C30—C31	1.4062 (17)
C14—C23	1.4461 (17)	C31—H31	0.9500
C15—H15	0.9500	C31—C32	1.3666 (17)
C15—C16	1.4062 (19)	C32—H32	0.9500
C16—H16	0.9500	C32—C33	1.4244 (17)
C1—O1—C13	114.75 (10)	C16—C17—H17	119.7
O1—C1—C2	116.60 (12)	C16—C17—C18	120.58 (13)
O1—C1—C10	120.87 (12)	C18—C17—H17	119.7
C10—C1—C2	122.50 (13)	C17—C18—C19	120.20 (13)
C1—C2—H2	120.4	C17—C18—C23	120.37 (12)
C3—C2—C1	119.12 (13)	C23—C18—C19	119.43 (13)
C3—C2—H2	120.4	C18—C19—H19	119.3
C2—C3—H3	119.4	C20—C19—C18	121.32 (13)
C2—C3—C4	121.30 (13)	C20—C19—H19	119.3
C4—C3—H3	119.4	C19—C20—H20	120.2
C3—C4—C5	121.64 (14)	C19—C20—C21	119.67 (13)
C3—C4—C9	119.23 (13)	C21—C20—H20	120.2
C9—C4—C5	119.09 (13)	C20—C21—H21	119.6
C4—C5—H5	119.6	C22—C21—C20	120.78 (13)
C6—C5—C4	120.87 (15)	C22—C21—H21	119.6
C6—C5—H5	119.6	C21—C22—H22	119.3
C5—C6—H6	120.0	C21—C22—C23	121.35 (13)
C5—C6—C7	120.06 (14)	C23—C22—H22	119.3
C7—C6—H6	120.0	C18—C23—C14	117.91 (12)
C6—C7—H7	119.6	C22—C23—C14	124.65 (12)
C8—C7—C6	120.88 (14)	C22—C23—C18	117.44 (12)
C8—C7—H7	119.6	C25—C24—C13	120.41 (11)
C7—C8—H8	119.8	C25—C24—C33	118.92 (11)
C7—C8—C9	120.42 (14)	C33—C24—C13	120.67 (11)
C9—C8—H8	119.8	C24—C25—H25	118.8
C4—C9—C8	118.65 (13)	C24—C25—C26	122.36 (12)
C4—C9—C10	119.12 (12)	C26—C25—H25	118.8
C8—C9—C10	122.19 (13)	C25—C26—H26	120.2
C1—C10—C9	118.68 (13)	C27—C26—C25	119.60 (12)
C1—C10—C11	116.78 (12)	C27—C26—H26	120.2
C9—C10—C11	124.53 (12)	C26—C27—H27	119.5
C10—C11—H11	120.2	C26—C27—C28	121.01 (12)
C12—C11—C10	119.59 (13)	C28—C27—H27	119.5
C12—C11—H11	120.2	C27—C28—C29	121.11 (12)
C11—C12—H12	119.6	C27—C28—C33	119.82 (11)
C11—C12—C13	120.73 (13)	C29—C28—C33	119.06 (11)
C13—C12—H12	119.6	C28—C29—H29	119.3
O1—C13—C12	107.89 (10)	C30—C29—C28	121.41 (12)
O1—C13—C14	107.37 (10)	C30—C29—H29	119.3
O1—C13—C24	107.18 (10)	C29—C30—H30	120.0
C12—C13—C14	108.20 (10)	C29—C30—C31	119.94 (12)
C12—C13—C24	112.75 (10)	C31—C30—H30	120.0
C14—C13—C24	113.18 (10)	C30—C31—H31	119.8
C15—C14—C13	119.17 (11)	C32—C31—C30	120.33 (13)
C15—C14—C23	118.99 (12)	C32—C31—H31	119.8
C23—C14—C13	121.56 (11)	C31—C32—H32	119.1
C14—C15—H15	118.8	C31—C32—C33	121.71 (12)
C14—C15—C16	122.49 (13)	C33—C32—H32	119.1
C16—C15—H15	118.8	C28—C33—C24	118.28 (11)
C15—C16—H16	120.2	C32—C33—C24	124.18 (11)
C17—C16—C15	119.62 (14)	C32—C33—C28	117.54 (11)
C17—C16—H16	120.2
O1—C1—C2—C3	−179.34 (10)	C13—C14—C23—C22	−4.57 (18)
O1—C1—C10—C9	179.78 (10)	C13—C24—C25—C26	−179.34 (12)
O1—C1—C10—C11	−1.38 (16)	C13—C24—C33—C28	179.55 (11)
O1—C13—C14—C15	−132.99 (12)	C13—C24—C33—C32	0.5 (2)
O1—C13—C14—C23	53.10 (14)	C14—C13—C24—C25	114.87 (14)
O1—C13—C24—C25	−126.95 (13)	C14—C13—C24—C33	−65.71 (16)
O1—C13—C24—C33	52.47 (15)	C14—C15—C16—C17	1.6 (2)
C1—O1—C13—C12	−49.81 (12)	C15—C14—C23—C18	0.98 (17)
C1—O1—C13—C14	−166.23 (9)	C15—C14—C23—C22	−178.49 (12)
C1—O1—C13—C24	71.88 (12)	C15—C16—C17—C18	0.1 (2)
C1—C2—C3—C4	−0.61 (19)	C16—C17—C18—C19	178.23 (13)
C1—C10—C11—C12	−17.40 (18)	C16—C17—C18—C23	−1.3 (2)
C2—C1—C10—C9	2.09 (17)	C17—C18—C19—C20	−179.69 (13)
C2—C1—C10—C11	−179.07 (11)	C17—C18—C23—C14	0.70 (18)
C2—C3—C4—C5	−175.22 (12)	C17—C18—C23—C22	−179.79 (12)
C2—C3—C4—C9	2.14 (18)	C18—C19—C20—C21	−0.5 (2)
C3—C4—C5—C6	177.50 (12)	C19—C18—C23—C14	−178.80 (11)
C3—C4—C9—C8	−179.17 (10)	C19—C18—C23—C22	0.71 (18)
C3—C4—C9—C10	−1.56 (18)	C19—C20—C21—C22	0.6 (2)
C4—C5—C6—C7	1.2 (2)	C20—C21—C22—C23	−0.03 (19)
C4—C9—C10—C1	−0.48 (17)	C21—C22—C23—C14	178.87 (12)
C4—C9—C10—C11	−179.24 (11)	C21—C22—C23—C18	−0.61 (18)
C5—C4—C9—C8	−1.74 (18)	C23—C14—C15—C16	−2.2 (2)
C5—C4—C9—C10	175.87 (11)	C23—C18—C19—C20	−0.2 (2)
C5—C6—C7—C8	−0.9 (2)	C24—C13—C14—C15	−14.91 (16)
C6—C7—C8—C9	−0.8 (2)	C24—C13—C14—C23	171.18 (10)
C7—C8—C9—C4	2.09 (18)	C24—C25—C26—C27	−0.6 (2)
C7—C8—C9—C10	−175.45 (12)	C25—C24—C33—C28	−1.02 (19)
C8—C9—C10—C1	177.04 (11)	C25—C24—C33—C32	179.90 (13)
C8—C9—C10—C11	−1.71 (19)	C25—C26—C27—C28	−0.1 (2)
C9—C4—C5—C6	0.13 (19)	C26—C27—C28—C29	−179.05 (13)
C9—C10—C11—C12	161.37 (12)	C26—C27—C28—C33	0.3 (2)
C10—C1—C2—C3	−1.56 (19)	C27—C28—C29—C30	179.63 (13)
C10—C11—C12—C13	−0.19 (18)	C27—C28—C33—C24	0.28 (18)
C11—C12—C13—O1	32.65 (15)	C27—C28—C33—C32	179.42 (12)
C11—C12—C13—C14	148.52 (12)	C28—C29—C30—C31	0.8 (2)
C11—C12—C13—C24	−85.52 (15)	C29—C28—C33—C24	179.65 (12)
C12—C13—C14—C15	110.80 (13)	C29—C28—C33—C32	−1.20 (18)
C12—C13—C14—C23	−63.11 (15)	C29—C30—C31—C32	−0.9 (2)
C12—C13—C24—C25	−8.37 (17)	C30—C31—C32—C33	−0.1 (2)
C12—C13—C24—C33	171.05 (11)	C31—C32—C33—C24	−179.75 (13)
C13—O1—C1—C2	−145.38 (11)	C31—C32—C33—C28	1.2 (2)
C13—O1—C1—C10	36.80 (14)	C33—C24—C25—C26	1.2 (2)
C13—C14—C15—C16	−176.24 (13)	C33—C28—C29—C30	0.3 (2)
C13—C14—C23—C18	174.90 (11)

3,3-Bis([1,1'-biphenyl]-4-yl)-3H-naphtho[2,1-b]pyran (NP2)

Crystal data

C37H26O	F(000) = 2048
Mr = 486.58	Dx = 1.248 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.960 (4) Å	Cell parameters from 18178 reflections
b = 23.880 (8) Å	θ = 1.3–28.1°
c = 20.385 (7) Å	µ = 0.07 mm^−1
β = 103.941 (5)°	T = 113 K
V = 5178 (3) Å^3	Prism, colorless
Z = 8	0.2 × 0.18 × 0.14 mm

Data collection

Bruker P4 diffractometer	6968 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.073
Detector resolution: 14.22 pixels mm^-1	θmax = 25.0°, θmin = 1.3°
ω scans	h = −13→13
42284 measured reflections	k = −26→28
9136 independent reflections	l = −24→24

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.067	w = 1/[σ^2(Fo^2) + (0.0853P)^2 + 0.2747P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.192	(Δ/σ)max = 0.001
S = 1.11	Δρmax = 0.54 e Å^−3
9136 reflections	Δρmin = −0.26 e Å^−3
686 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0050 (6)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.58120 (14)	0.14284 (6)	0.19415 (8)	0.0331 (4)
O2	0.44537 (14)	0.08748 (6)	0.36916 (8)	0.0330 (4)
C1	0.6911 (2)	0.11910 (9)	0.18492 (13)	0.0319 (6)
C2	0.7764 (2)	0.09771 (9)	0.24269 (13)	0.0347 (6)
H2	0.758687	0.100460	0.285950	0.042*
C3	0.8853 (2)	0.07292 (10)	0.23558 (13)	0.0369 (6)
H3	0.942459	0.058120	0.274316	0.044*
C4	0.9144 (2)	0.06888 (9)	0.17176 (13)	0.0348 (6)
C5	1.0251 (2)	0.04151 (10)	0.16393 (14)	0.0395 (6)
H5	1.081959	0.025914	0.202245	0.047*
C6	1.0504 (2)	0.03748 (10)	0.10164 (15)	0.0418 (7)
H6	1.123824	0.018424	0.096786	0.050*
C7	0.9677 (2)	0.06156 (10)	0.04422 (14)	0.0401 (6)
H7	0.986533	0.058829	0.001203	0.048*
C8	0.8611 (2)	0.08868 (10)	0.05032 (14)	0.0369 (6)
H8	0.807322	0.105035	0.011471	0.044*
C9	0.8294 (2)	0.09284 (9)	0.11369 (13)	0.0324 (6)
C10	0.7160 (2)	0.11860 (9)	0.12179 (13)	0.0316 (6)
C11	0.6228 (2)	0.14584 (9)	0.06678 (13)	0.0339 (6)
H11	0.645967	0.158233	0.027178	0.041*
C12	0.5069 (2)	0.15281 (10)	0.07316 (13)	0.0346 (6)
H12	0.445440	0.170056	0.038087	0.041*
C13	0.4727 (2)	0.13291 (10)	0.13736 (13)	0.0328 (6)
C14	0.3639 (2)	0.16729 (9)	0.15071 (13)	0.0337 (6)
C15	0.3813 (2)	0.21612 (10)	0.18920 (13)	0.0381 (6)
H15	0.464053	0.228861	0.209198	0.046*
C16	0.2786 (2)	0.24624 (10)	0.19850 (14)	0.0392 (6)
H16	0.293063	0.278880	0.225922	0.047*
C17	0.1553 (2)	0.23058 (9)	0.16930 (12)	0.0321 (6)
C18	0.1387 (2)	0.18126 (10)	0.12990 (13)	0.0369 (6)
H18	0.056134	0.168812	0.109129	0.044*
C19	0.2408 (2)	0.15089 (10)	0.12115 (13)	0.0357 (6)
H19	0.226783	0.117935	0.094274	0.043*
C20	0.0443 (2)	0.26195 (10)	0.17944 (13)	0.0362 (6)
C21	0.0534 (3)	0.31812 (11)	0.19900 (16)	0.0503 (8)
H21	0.132501	0.336478	0.206502	0.060*
C22	−0.0499 (3)	0.34757 (12)	0.20769 (17)	0.0569 (8)
H22	−0.041493	0.386099	0.219534	0.068*
C23	−0.1659 (3)	0.32159 (11)	0.19932 (16)	0.0505 (7)
H23	−0.236453	0.341825	0.206173	0.061*
C24	−0.1770 (2)	0.26619 (11)	0.18098 (16)	0.0519 (8)
H24	−0.256080	0.247932	0.174208	0.062*
C25	−0.0730 (2)	0.23693 (11)	0.17236 (15)	0.0475 (7)
H25	−0.081970	0.198281	0.161182	0.057*
C26	0.4415 (2)	0.07001 (9)	0.13709 (13)	0.0323 (6)
C27	0.4271 (2)	0.03619 (9)	0.08019 (13)	0.0348 (6)
H27	0.445106	0.050846	0.040233	0.042*
C28	0.3863 (2)	−0.01900 (10)	0.08127 (13)	0.0362 (6)
H28	0.378300	−0.041659	0.042158	0.043*
C29	0.3570 (2)	−0.04165 (10)	0.13889 (14)	0.0352 (6)
C30	0.3760 (2)	−0.00794 (10)	0.19670 (13)	0.0354 (6)
H30	0.359321	−0.022788	0.236902	0.042*
C31	0.4185 (2)	0.04668 (10)	0.19633 (13)	0.0364 (6)
H31	0.432205	0.068534	0.236381	0.044*
C32	0.3014 (2)	−0.09873 (9)	0.13702 (13)	0.0356 (6)
C33	0.3494 (2)	−0.14383 (10)	0.10855 (14)	0.0420 (6)
H33	0.423135	−0.139002	0.092396	0.050*
C34	0.2918 (3)	−0.19583 (10)	0.10325 (15)	0.0485 (7)
H34	0.326928	−0.226242	0.083973	0.058*
C35	0.1838 (3)	−0.20389 (12)	0.12575 (15)	0.0520 (8)
H35	0.142534	−0.239167	0.120686	0.062*
C36	0.1371 (2)	−0.15946 (11)	0.15580 (15)	0.0482 (7)
H36	0.064276	−0.164746	0.172633	0.058*
C37	0.1942 (2)	−0.10768 (10)	0.16176 (14)	0.0422 (7)
H37	0.160696	−0.077823	0.182780	0.051*
C38	0.3358 (2)	0.11252 (9)	0.37618 (13)	0.0320 (6)
C39	0.2475 (2)	0.12765 (9)	0.31588 (13)	0.0344 (6)
H39	0.265561	0.121401	0.273181	0.041*
C40	0.1357 (2)	0.15138 (9)	0.31977 (13)	0.0356 (6)
H40	0.075560	0.160727	0.279323	0.043*
C41	0.1081 (2)	0.16225 (9)	0.38293 (14)	0.0350 (6)
C42	−0.0060 (2)	0.18830 (10)	0.38759 (15)	0.0427 (7)
H42	−0.067235	0.197374	0.347441	0.051*
C43	−0.0290 (2)	0.20053 (11)	0.44914 (16)	0.0507 (8)
H43	−0.106339	0.217412	0.451426	0.061*
C44	0.0620 (3)	0.18809 (12)	0.50924 (17)	0.0566 (8)
H44	0.047148	0.198302	0.551684	0.068*
C45	0.1718 (2)	0.16135 (11)	0.50680 (15)	0.0475 (7)
H45	0.231043	0.152259	0.547687	0.057*
C46	0.1978 (2)	0.14714 (10)	0.44396 (14)	0.0355 (6)
C47	0.3124 (2)	0.12026 (9)	0.43931 (13)	0.0339 (6)
C48	0.4044 (2)	0.09629 (10)	0.49697 (13)	0.0378 (6)
H48	0.381971	0.089625	0.538493	0.045*
C49	0.5194 (2)	0.08397 (10)	0.49063 (13)	0.0365 (6)
H49	0.578293	0.066107	0.526337	0.044*
C50	0.5546 (2)	0.09904 (9)	0.42508 (13)	0.0328 (6)
C51	0.5890 (2)	0.16104 (9)	0.42082 (13)	0.0320 (6)
C52	0.6134 (2)	0.19676 (10)	0.47614 (13)	0.0364 (6)
H52	0.604024	0.183510	0.518595	0.044*
C53	0.6516 (2)	0.25203 (10)	0.47019 (14)	0.0379 (6)
H53	0.667609	0.275843	0.508653	0.045*
C54	0.6665 (2)	0.27272 (9)	0.40852 (13)	0.0345 (6)
C55	0.6406 (2)	0.23667 (9)	0.35294 (13)	0.0349 (6)
H55	0.649054	0.249905	0.310307	0.042*
C56	0.6026 (2)	0.18177 (9)	0.35892 (13)	0.0344 (6)
H56	0.585665	0.158028	0.320395	0.041*
C57	0.7078 (2)	0.33169 (10)	0.40165 (14)	0.0371 (6)
C58	0.6647 (2)	0.37594 (10)	0.43542 (15)	0.0446 (7)
H58	0.610359	0.368148	0.464202	0.054*
C59	0.6999 (2)	0.43047 (11)	0.42764 (16)	0.0514 (8)
H59	0.669836	0.459722	0.451160	0.062*
C60	0.7785 (2)	0.44292 (11)	0.38587 (16)	0.0486 (7)
H60	0.801962	0.480593	0.380244	0.058*
C61	0.8222 (3)	0.40057 (11)	0.35279 (17)	0.0542 (8)
H61	0.876574	0.408931	0.324188	0.065*
C62	0.7878 (2)	0.34488 (11)	0.36050 (16)	0.0481 (7)
H62	0.819537	0.315878	0.337346	0.058*
C63	0.6628 (2)	0.06260 (9)	0.41388 (13)	0.0316 (6)
C64	0.7845 (2)	0.07480 (10)	0.44997 (13)	0.0379 (6)
H64	0.797697	0.104297	0.482174	0.046*
C65	0.8873 (2)	0.04494 (10)	0.44010 (13)	0.0375 (6)
H65	0.969356	0.054375	0.465423	0.045*
C66	0.8714 (2)	0.00124 (9)	0.39344 (13)	0.0339 (6)
C67	0.7488 (2)	−0.01182 (9)	0.35863 (14)	0.0387 (6)
H67	0.735501	−0.041885	0.327179	0.046*
C68	0.6449 (2)	0.01795 (9)	0.36859 (13)	0.0357 (6)
H68	0.562397	0.007774	0.344576	0.043*
C69	0.9827 (2)	−0.02845 (9)	0.37990 (13)	0.0363 (6)
C70	1.0947 (2)	−0.00026 (10)	0.38257 (13)	0.0385 (6)
H70	1.100636	0.038396	0.393889	0.046*
C71	1.1985 (3)	−0.02743 (11)	0.36902 (15)	0.0471 (7)
H71	1.273895	−0.007353	0.370501	0.057*
C72	1.1907 (3)	−0.08365 (13)	0.35348 (17)	0.0586 (9)
H72	1.260632	−0.102346	0.343567	0.070*
C73	1.0820 (3)	−0.11279 (13)	0.35226 (19)	0.0673 (10)
H73	1.077965	−0.151756	0.342585	0.081*
C74	0.9776 (3)	−0.08555 (11)	0.36512 (16)	0.0526 (8)
H74	0.902731	−0.105984	0.363800	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0307 (9)	0.0355 (9)	0.0330 (10)	0.0007 (7)	0.0074 (7)	−0.0017 (7)
O2	0.0289 (9)	0.0339 (9)	0.0357 (11)	0.0031 (7)	0.0072 (7)	0.0001 (7)
C1	0.0285 (12)	0.0301 (13)	0.0389 (16)	−0.0017 (10)	0.0116 (11)	−0.0008 (10)
C2	0.0332 (13)	0.0355 (14)	0.0354 (15)	−0.0019 (10)	0.0085 (11)	0.0016 (10)
C3	0.0318 (13)	0.0379 (14)	0.0390 (16)	−0.0037 (11)	0.0043 (11)	0.0042 (11)
C4	0.0320 (13)	0.0296 (13)	0.0430 (17)	−0.0029 (10)	0.0098 (11)	−0.0003 (11)
C5	0.0321 (14)	0.0368 (14)	0.0491 (18)	0.0022 (11)	0.0088 (12)	0.0004 (12)
C6	0.0338 (14)	0.0382 (14)	0.055 (2)	0.0038 (11)	0.0132 (13)	−0.0023 (12)
C7	0.0394 (14)	0.0353 (14)	0.0488 (18)	−0.0014 (11)	0.0170 (13)	−0.0038 (12)
C8	0.0349 (14)	0.0345 (14)	0.0424 (17)	−0.0014 (11)	0.0114 (12)	0.0019 (11)
C9	0.0287 (13)	0.0302 (13)	0.0398 (16)	−0.0041 (10)	0.0109 (11)	−0.0009 (10)
C10	0.0298 (12)	0.0280 (12)	0.0373 (16)	−0.0037 (10)	0.0086 (11)	0.0006 (10)
C11	0.0339 (13)	0.0311 (13)	0.0382 (16)	−0.0002 (10)	0.0117 (11)	0.0041 (10)
C12	0.0341 (14)	0.0359 (14)	0.0334 (15)	−0.0027 (10)	0.0075 (11)	0.0019 (10)
C13	0.0283 (12)	0.0358 (14)	0.0335 (15)	−0.0019 (10)	0.0058 (11)	0.0001 (10)
C14	0.0347 (13)	0.0331 (13)	0.0347 (15)	−0.0006 (10)	0.0113 (11)	0.0036 (10)
C15	0.0344 (14)	0.0325 (14)	0.0473 (17)	−0.0049 (11)	0.0097 (12)	−0.0040 (11)
C16	0.0416 (14)	0.0267 (13)	0.0496 (18)	−0.0018 (11)	0.0119 (12)	−0.0060 (11)
C17	0.0355 (13)	0.0286 (13)	0.0339 (15)	−0.0001 (10)	0.0118 (11)	0.0047 (10)
C18	0.0319 (13)	0.0396 (14)	0.0380 (16)	−0.0009 (11)	0.0063 (11)	−0.0016 (11)
C19	0.0331 (13)	0.0341 (14)	0.0403 (16)	−0.0021 (10)	0.0094 (11)	−0.0047 (11)
C20	0.0396 (14)	0.0304 (13)	0.0386 (16)	0.0033 (11)	0.0093 (11)	0.0051 (11)
C21	0.0450 (16)	0.0385 (15)	0.070 (2)	0.0004 (12)	0.0181 (15)	−0.0039 (13)
C22	0.0567 (19)	0.0399 (16)	0.076 (2)	0.0099 (14)	0.0203 (17)	−0.0037 (15)
C23	0.0438 (16)	0.0488 (17)	0.058 (2)	0.0177 (13)	0.0105 (14)	−0.0001 (14)
C24	0.0354 (15)	0.0481 (17)	0.072 (2)	0.0035 (12)	0.0122 (14)	−0.0041 (14)
C25	0.0381 (15)	0.0381 (15)	0.065 (2)	0.0015 (12)	0.0098 (13)	−0.0075 (13)
C26	0.0290 (12)	0.0342 (13)	0.0339 (15)	0.0014 (10)	0.0077 (11)	0.0007 (10)
C27	0.0313 (13)	0.0355 (14)	0.0399 (16)	−0.0008 (10)	0.0128 (11)	0.0015 (11)
C28	0.0344 (13)	0.0363 (14)	0.0396 (16)	−0.0002 (11)	0.0124 (11)	−0.0033 (11)
C29	0.0273 (12)	0.0339 (14)	0.0445 (17)	0.0041 (10)	0.0086 (11)	0.0073 (11)
C30	0.0362 (14)	0.0352 (14)	0.0353 (16)	0.0017 (11)	0.0096 (11)	0.0028 (11)
C31	0.0353 (13)	0.0353 (14)	0.0386 (16)	0.0009 (11)	0.0086 (11)	0.0010 (11)
C32	0.0317 (13)	0.0322 (13)	0.0405 (16)	0.0014 (10)	0.0042 (11)	0.0050 (11)
C33	0.0405 (15)	0.0392 (15)	0.0455 (18)	−0.0018 (12)	0.0092 (12)	0.0040 (12)
C34	0.0602 (18)	0.0302 (14)	0.055 (2)	0.0012 (13)	0.0144 (15)	0.0039 (12)
C35	0.0503 (17)	0.0419 (16)	0.058 (2)	−0.0117 (13)	0.0026 (14)	0.0099 (14)
C36	0.0389 (15)	0.0454 (17)	0.057 (2)	−0.0038 (12)	0.0051 (13)	0.0127 (13)
C37	0.0379 (14)	0.0392 (15)	0.0480 (18)	0.0020 (11)	0.0073 (12)	0.0062 (12)
C38	0.0298 (13)	0.0255 (12)	0.0415 (16)	0.0003 (10)	0.0100 (11)	0.0028 (10)
C39	0.0333 (13)	0.0334 (13)	0.0367 (15)	−0.0013 (10)	0.0087 (11)	0.0022 (11)
C40	0.0312 (13)	0.0319 (13)	0.0410 (16)	−0.0015 (10)	0.0034 (11)	0.0046 (11)
C41	0.0303 (13)	0.0284 (13)	0.0476 (17)	0.0002 (10)	0.0116 (12)	0.0015 (11)
C42	0.0325 (14)	0.0381 (14)	0.057 (2)	0.0025 (11)	0.0092 (13)	0.0027 (12)
C43	0.0378 (15)	0.0509 (17)	0.066 (2)	0.0129 (13)	0.0182 (15)	0.0065 (15)
C44	0.0539 (18)	0.066 (2)	0.055 (2)	0.0154 (15)	0.0238 (16)	−0.0036 (15)
C45	0.0384 (15)	0.0576 (18)	0.0471 (19)	0.0131 (13)	0.0116 (13)	0.0020 (13)
C46	0.0320 (13)	0.0331 (13)	0.0428 (17)	0.0024 (10)	0.0119 (12)	0.0020 (11)
C47	0.0329 (13)	0.0315 (13)	0.0392 (16)	0.0030 (10)	0.0123 (11)	0.0033 (10)
C48	0.0386 (14)	0.0415 (15)	0.0357 (16)	0.0046 (11)	0.0136 (12)	0.0040 (11)
C49	0.0360 (14)	0.0364 (14)	0.0371 (16)	0.0073 (11)	0.0085 (11)	0.0059 (11)
C50	0.0278 (12)	0.0337 (13)	0.0353 (15)	0.0036 (10)	0.0048 (11)	−0.0012 (10)
C51	0.0256 (12)	0.0309 (13)	0.0395 (16)	0.0088 (10)	0.0080 (11)	0.0030 (10)
C52	0.0341 (13)	0.0379 (14)	0.0376 (16)	0.0063 (11)	0.0095 (11)	−0.0023 (11)
C53	0.0360 (14)	0.0353 (14)	0.0429 (17)	0.0022 (11)	0.0106 (12)	−0.0095 (11)
C54	0.0264 (12)	0.0307 (13)	0.0453 (17)	0.0058 (10)	0.0068 (11)	−0.0047 (11)
C55	0.0334 (13)	0.0316 (13)	0.0403 (16)	0.0044 (10)	0.0102 (11)	0.0031 (10)
C56	0.0350 (13)	0.0300 (13)	0.0378 (16)	0.0058 (10)	0.0077 (11)	−0.0040 (10)
C57	0.0271 (12)	0.0331 (13)	0.0500 (18)	0.0035 (10)	0.0072 (12)	−0.0012 (11)
C58	0.0379 (14)	0.0374 (15)	0.057 (2)	0.0050 (12)	0.0085 (13)	−0.0051 (12)
C59	0.0394 (15)	0.0368 (16)	0.074 (2)	0.0031 (12)	0.0058 (15)	−0.0110 (14)
C60	0.0398 (15)	0.0322 (14)	0.073 (2)	−0.0012 (12)	0.0121 (15)	−0.0041 (13)
C61	0.0450 (17)	0.0438 (17)	0.077 (2)	−0.0036 (13)	0.0201 (16)	0.0040 (15)
C62	0.0429 (16)	0.0367 (15)	0.065 (2)	0.0048 (12)	0.0144 (14)	−0.0044 (13)
C63	0.0351 (13)	0.0284 (13)	0.0343 (15)	0.0043 (10)	0.0138 (11)	0.0032 (10)
C64	0.0355 (14)	0.0385 (14)	0.0390 (16)	0.0071 (11)	0.0075 (12)	−0.0056 (11)
C65	0.0343 (13)	0.0350 (14)	0.0425 (17)	0.0076 (11)	0.0079 (11)	0.0020 (11)
C66	0.0347 (13)	0.0258 (12)	0.0431 (16)	0.0040 (10)	0.0128 (12)	0.0051 (10)
C67	0.0433 (15)	0.0246 (13)	0.0501 (18)	0.0013 (11)	0.0148 (13)	−0.0019 (11)
C68	0.0330 (13)	0.0291 (13)	0.0456 (17)	0.0003 (10)	0.0102 (11)	0.0021 (11)
C69	0.0410 (14)	0.0291 (13)	0.0404 (16)	0.0086 (11)	0.0131 (12)	0.0022 (10)
C70	0.0364 (14)	0.0367 (14)	0.0424 (17)	0.0066 (11)	0.0094 (12)	0.0036 (11)
C71	0.0394 (15)	0.0514 (17)	0.0521 (19)	0.0093 (12)	0.0138 (13)	0.0067 (13)
C72	0.0473 (18)	0.061 (2)	0.072 (2)	0.0135 (15)	0.0238 (16)	−0.0119 (16)
C73	0.057 (2)	0.0456 (18)	0.102 (3)	0.0066 (15)	0.0258 (19)	−0.0260 (17)
C74	0.0423 (16)	0.0414 (16)	0.075 (2)	0.0036 (12)	0.0165 (15)	−0.0106 (14)

Geometric parameters (Å, º)

O1—C1	1.384 (3)	C36—C37	1.378 (3)
O1—C13	1.465 (3)	C37—H37	0.9500
O2—C38	1.379 (3)	C38—C39	1.416 (3)
O2—C50	1.466 (3)	C38—C47	1.384 (3)
C1—C2	1.412 (3)	C39—H39	0.9500
C1—C10	1.379 (3)	C39—C40	1.369 (3)
C2—H2	0.9500	C40—H40	0.9500
C2—C3	1.371 (3)	C40—C41	1.416 (3)
C3—H3	0.9500	C41—C42	1.420 (3)
C3—C4	1.415 (3)	C41—C46	1.434 (4)
C4—C5	1.421 (3)	C42—H42	0.9500
C4—C9	1.437 (3)	C42—C43	1.370 (4)
C5—H5	0.9500	C43—H43	0.9500
C5—C6	1.367 (4)	C43—C44	1.412 (4)
C6—H6	0.9500	C44—H44	0.9500
C6—C7	1.418 (4)	C44—C45	1.374 (3)
C7—H7	0.9500	C45—H45	0.9500
C7—C8	1.368 (3)	C45—C46	1.419 (4)
C8—H8	0.9500	C46—C47	1.434 (3)
C8—C9	1.419 (3)	C47—C48	1.468 (3)
C9—C10	1.432 (3)	C48—H48	0.9500
C10—C11	1.474 (3)	C48—C49	1.330 (3)
C11—H11	0.9500	C49—H49	0.9500
C11—C12	1.318 (3)	C49—C50	1.521 (3)
C12—H12	0.9500	C50—C51	1.535 (3)
C12—C13	1.522 (3)	C50—C63	1.532 (3)
C13—C14	1.526 (3)	C51—C52	1.388 (3)
C13—C26	1.540 (3)	C51—C56	1.396 (3)
C14—C15	1.393 (3)	C52—H52	0.9500
C14—C19	1.395 (3)	C52—C53	1.399 (3)
C15—H15	0.9500	C53—H53	0.9500
C15—C16	1.387 (3)	C53—C54	1.397 (3)
C16—H16	0.9500	C54—C55	1.397 (3)
C16—C17	1.390 (3)	C54—C57	1.496 (3)
C17—C18	1.412 (3)	C55—H55	0.9500
C17—C20	1.485 (3)	C55—C56	1.390 (3)
C18—H18	0.9500	C56—H56	0.9500
C18—C19	1.380 (3)	C57—C58	1.403 (3)
C19—H19	0.9500	C57—C62	1.388 (4)
C20—C21	1.396 (3)	C58—H58	0.9500
C20—C25	1.394 (3)	C58—C59	1.378 (4)
C21—H21	0.9500	C59—H59	0.9500
C21—C22	1.380 (4)	C59—C60	1.382 (4)
C22—H22	0.9500	C60—H60	0.9500
C22—C23	1.388 (4)	C60—C61	1.365 (4)
C23—H23	0.9500	C61—H61	0.9500
C23—C24	1.372 (4)	C61—C62	1.401 (4)
C24—H24	0.9500	C62—H62	0.9500
C24—C25	1.384 (3)	C63—C64	1.390 (3)
C25—H25	0.9500	C63—C68	1.393 (3)
C26—C27	1.391 (3)	C64—H64	0.9500
C26—C31	1.407 (3)	C64—C65	1.388 (3)
C27—H27	0.9500	C65—H65	0.9500
C27—C28	1.393 (3)	C65—C66	1.394 (3)
C28—H28	0.9500	C66—C67	1.396 (3)
C28—C29	1.399 (3)	C66—C69	1.493 (3)
C29—C30	1.401 (3)	C67—H67	0.9500
C29—C32	1.490 (3)	C67—C68	1.398 (3)
C30—H30	0.9500	C68—H68	0.9500
C30—C31	1.386 (3)	C69—C70	1.389 (3)
C31—H31	0.9500	C69—C74	1.395 (3)
C32—C33	1.386 (3)	C70—H70	0.9500
C32—C37	1.402 (3)	C70—C71	1.394 (3)
C33—H33	0.9500	C71—H71	0.9500
C33—C34	1.385 (3)	C71—C72	1.377 (4)
C34—H34	0.9500	C72—H72	0.9500
C34—C35	1.382 (4)	C72—C73	1.374 (4)
C35—H35	0.9500	C73—H73	0.9500
C35—C36	1.384 (4)	C73—C74	1.395 (4)
C36—H36	0.9500	C74—H74	0.9500
C1—O1—C13	113.16 (17)	C36—C37—H37	119.8
C38—O2—C50	113.93 (17)	O2—C38—C39	116.8 (2)
O1—C1—C2	117.3 (2)	O2—C38—C47	121.0 (2)
C10—C1—O1	120.3 (2)	C47—C38—C39	122.2 (2)
C10—C1—C2	122.3 (2)	C38—C39—H39	120.3
C1—C2—H2	120.4	C40—C39—C38	119.3 (2)
C3—C2—C1	119.1 (2)	C40—C39—H39	120.3
C3—C2—H2	120.4	C39—C40—H40	119.4
C2—C3—H3	119.3	C39—C40—C41	121.3 (2)
C2—C3—C4	121.4 (2)	C41—C40—H40	119.4
C4—C3—H3	119.3	C40—C41—C42	121.7 (2)
C3—C4—C5	121.5 (2)	C40—C41—C46	119.4 (2)
C3—C4—C9	119.0 (2)	C42—C41—C46	118.9 (2)
C5—C4—C9	119.5 (2)	C41—C42—H42	119.5
C4—C5—H5	119.8	C43—C42—C41	120.9 (3)
C6—C5—C4	120.5 (2)	C43—C42—H42	119.5
C6—C5—H5	119.8	C42—C43—H43	119.9
C5—C6—H6	119.8	C42—C43—C44	120.2 (2)
C5—C6—C7	120.4 (2)	C44—C43—H43	119.9
C7—C6—H6	119.8	C43—C44—H44	119.7
C6—C7—H7	119.8	C45—C44—C43	120.5 (3)
C8—C7—C6	120.5 (3)	C45—C44—H44	119.7
C8—C7—H7	119.8	C44—C45—H45	119.6
C7—C8—H8	119.4	C44—C45—C46	120.8 (3)
C7—C8—C9	121.2 (2)	C46—C45—H45	119.6
C9—C8—H8	119.4	C41—C46—C47	118.9 (2)
C8—C9—C4	118.0 (2)	C45—C46—C41	118.6 (2)
C8—C9—C10	123.0 (2)	C45—C46—C47	122.4 (2)
C10—C9—C4	119.0 (2)	C38—C47—C46	118.9 (2)
C1—C10—C9	119.0 (2)	C38—C47—C48	116.6 (2)
C1—C10—C11	116.7 (2)	C46—C47—C48	124.4 (2)
C9—C10—C11	124.3 (2)	C47—C48—H48	120.3
C10—C11—H11	120.4	C49—C48—C47	119.5 (2)
C12—C11—C10	119.2 (2)	C49—C48—H48	120.3
C12—C11—H11	120.4	C48—C49—H49	120.7
C11—C12—H12	120.4	C48—C49—C50	118.7 (2)
C11—C12—C13	119.2 (2)	C50—C49—H49	120.7
C13—C12—H12	120.4	O2—C50—C49	107.83 (18)
O1—C13—C12	107.94 (18)	O2—C50—C51	107.65 (18)
O1—C13—C14	107.01 (19)	O2—C50—C63	107.07 (19)
O1—C13—C26	107.33 (18)	C49—C50—C51	113.32 (19)
C12—C13—C14	110.51 (19)	C49—C50—C63	111.48 (19)
C12—C13—C26	113.7 (2)	C63—C50—C51	109.23 (18)
C14—C13—C26	110.06 (18)	C52—C51—C50	123.3 (2)
C15—C14—C13	122.9 (2)	C52—C51—C56	118.3 (2)
C15—C14—C19	117.8 (2)	C56—C51—C50	118.3 (2)
C19—C14—C13	119.2 (2)	C51—C52—H52	119.6
C14—C15—H15	119.8	C51—C52—C53	120.8 (2)
C16—C15—C14	120.3 (2)	C53—C52—H52	119.6
C16—C15—H15	119.8	C52—C53—H53	119.5
C15—C16—H16	118.7	C54—C53—C52	120.9 (2)
C15—C16—C17	122.6 (2)	C54—C53—H53	119.5
C17—C16—H16	118.7	C53—C54—C57	121.4 (2)
C16—C17—C18	116.5 (2)	C55—C54—C53	117.8 (2)
C16—C17—C20	123.3 (2)	C55—C54—C57	120.8 (2)
C18—C17—C20	120.2 (2)	C54—C55—H55	119.4
C17—C18—H18	119.5	C56—C55—C54	121.1 (2)
C19—C18—C17	121.0 (2)	C56—C55—H55	119.4
C19—C18—H18	119.5	C51—C56—H56	119.6
C14—C19—H19	119.1	C55—C56—C51	120.9 (2)
C18—C19—C14	121.8 (2)	C55—C56—H56	119.6
C18—C19—H19	119.1	C58—C57—C54	121.2 (2)
C21—C20—C17	121.3 (2)	C62—C57—C54	121.3 (2)
C25—C20—C17	122.4 (2)	C62—C57—C58	117.5 (2)
C25—C20—C21	116.2 (2)	C57—C58—H58	119.4
C20—C21—H21	119.3	C59—C58—C57	121.3 (3)
C22—C21—C20	121.5 (3)	C59—C58—H58	119.4
C22—C21—H21	119.3	C58—C59—H59	119.8
C21—C22—H22	119.6	C58—C59—C60	120.5 (3)
C21—C22—C23	120.8 (3)	C60—C59—H59	119.8
C23—C22—H22	119.6	C59—C60—H60	120.3
C22—C23—H23	120.6	C61—C60—C59	119.3 (3)
C24—C23—C22	118.9 (2)	C61—C60—H60	120.3
C24—C23—H23	120.6	C60—C61—H61	119.6
C23—C24—H24	120.0	C60—C61—C62	120.8 (3)
C23—C24—C25	120.0 (3)	C62—C61—H61	119.6
C25—C24—H24	120.0	C57—C62—C61	120.6 (2)
C20—C25—H25	118.7	C57—C62—H62	119.7
C24—C25—C20	122.6 (2)	C61—C62—H62	119.7
C24—C25—H25	118.7	C64—C63—C50	118.7 (2)
C27—C26—C13	123.4 (2)	C64—C63—C68	118.4 (2)
C27—C26—C31	118.5 (2)	C68—C63—C50	122.9 (2)
C31—C26—C13	118.0 (2)	C63—C64—H64	119.2
C26—C27—H27	119.7	C65—C64—C63	121.6 (2)
C26—C27—C28	120.6 (2)	C65—C64—H64	119.2
C28—C27—H27	119.7	C64—C65—H65	119.6
C27—C28—H28	119.4	C64—C65—C66	120.7 (2)
C27—C28—C29	121.2 (2)	C66—C65—H65	119.6
C29—C28—H28	119.4	C65—C66—C67	117.5 (2)
C28—C29—C30	117.8 (2)	C65—C66—C69	120.5 (2)
C28—C29—C32	120.5 (2)	C67—C66—C69	122.0 (2)
C30—C29—C32	121.6 (2)	C66—C67—H67	119.0
C29—C30—H30	119.4	C66—C67—C68	122.1 (2)
C31—C30—C29	121.2 (2)	C68—C67—H67	119.0
C31—C30—H30	119.4	C63—C68—C67	119.7 (2)
C26—C31—H31	119.7	C63—C68—H68	120.2
C30—C31—C26	120.5 (2)	C67—C68—H68	120.2
C30—C31—H31	119.7	C70—C69—C66	121.1 (2)
C33—C32—C29	121.8 (2)	C70—C69—C74	118.1 (2)
C33—C32—C37	117.9 (2)	C74—C69—C66	120.8 (2)
C37—C32—C29	120.2 (2)	C69—C70—H70	119.3
C32—C33—H33	119.4	C69—C70—C71	121.5 (2)
C34—C33—C32	121.1 (2)	C71—C70—H70	119.3
C34—C33—H33	119.4	C70—C71—H71	120.3
C33—C34—H34	119.7	C72—C71—C70	119.4 (3)
C35—C34—C33	120.6 (3)	C72—C71—H71	120.3
C35—C34—H34	119.7	C71—C72—H72	119.9
C34—C35—H35	120.7	C73—C72—C71	120.2 (3)
C34—C35—C36	118.6 (3)	C73—C72—H72	119.9
C36—C35—H35	120.7	C72—C73—H73	119.8
C35—C36—H36	119.4	C72—C73—C74	120.5 (3)
C37—C36—C35	121.2 (3)	C74—C73—H73	119.8
C37—C36—H36	119.4	C69—C74—H74	119.8
C32—C37—H37	119.8	C73—C74—C69	120.3 (3)
C36—C37—C32	120.5 (2)	C73—C74—H74	119.8
O1—C1—C2—C3	178.80 (19)	C32—C29—C30—C31	−174.9 (2)
O1—C1—C10—C9	−178.90 (18)	C32—C33—C34—C35	0.6 (4)
O1—C1—C10—C11	1.9 (3)	C33—C32—C37—C36	−1.9 (4)
O1—C13—C14—C15	27.0 (3)	C33—C34—C35—C36	−2.3 (4)
O1—C13—C14—C19	−155.7 (2)	C34—C35—C36—C37	1.8 (4)
O1—C13—C26—C27	−128.6 (2)	C35—C36—C37—C32	0.3 (4)
O1—C13—C26—C31	55.8 (3)	C37—C32—C33—C34	1.4 (4)
O2—C38—C39—C40	178.40 (19)	C38—O2—C50—C49	52.9 (2)
O2—C38—C47—C46	179.22 (19)	C38—O2—C50—C51	−69.6 (2)
O2—C38—C47—C48	−5.1 (3)	C38—O2—C50—C63	173.02 (17)
O2—C50—C51—C52	132.9 (2)	C38—C39—C40—C41	1.5 (3)
O2—C50—C51—C56	−50.4 (3)	C38—C47—C48—C49	19.9 (3)
O2—C50—C63—C64	164.8 (2)	C39—C38—C47—C46	−3.3 (3)
O2—C50—C63—C68	−14.6 (3)	C39—C38—C47—C48	172.4 (2)
C1—O1—C13—C12	−54.1 (2)	C39—C40—C41—C42	178.2 (2)
C1—O1—C13—C14	−173.09 (17)	C39—C40—C41—C46	−1.2 (3)
C1—O1—C13—C26	68.8 (2)	C40—C41—C42—C43	−177.4 (2)
C1—C2—C3—C4	0.7 (3)	C40—C41—C46—C45	176.3 (2)
C1—C10—C11—C12	−21.5 (3)	C40—C41—C46—C47	−1.3 (3)
C2—C1—C10—C9	3.4 (3)	C41—C42—C43—C44	1.0 (4)
C2—C1—C10—C11	−175.8 (2)	C41—C46—C47—C38	3.5 (3)
C2—C3—C4—C5	−177.8 (2)	C41—C46—C47—C48	−171.9 (2)
C2—C3—C4—C9	1.9 (3)	C42—C41—C46—C45	−3.1 (3)
C3—C4—C5—C6	179.1 (2)	C42—C41—C46—C47	179.3 (2)
C3—C4—C9—C8	179.5 (2)	C42—C43—C44—C45	−3.0 (4)
C3—C4—C9—C10	−1.8 (3)	C43—C44—C45—C46	1.9 (4)
C4—C5—C6—C7	1.3 (4)	C44—C45—C46—C41	1.2 (4)
C4—C9—C10—C1	−0.7 (3)	C44—C45—C46—C47	178.7 (2)
C4—C9—C10—C11	178.4 (2)	C45—C46—C47—C38	−174.0 (2)
C5—C4—C9—C8	−0.8 (3)	C45—C46—C47—C48	10.6 (4)
C5—C4—C9—C10	177.8 (2)	C46—C41—C42—C43	2.0 (4)
C5—C6—C7—C8	−0.6 (4)	C46—C47—C48—C49	−164.7 (2)
C6—C7—C8—C9	−0.9 (4)	C47—C38—C39—C40	0.8 (3)
C7—C8—C9—C4	1.5 (3)	C47—C48—C49—C50	4.3 (4)
C7—C8—C9—C10	−177.1 (2)	C48—C49—C50—O2	−39.5 (3)
C8—C9—C10—C1	177.9 (2)	C48—C49—C50—C51	79.5 (3)
C8—C9—C10—C11	−3.0 (4)	C48—C49—C50—C63	−156.7 (2)
C9—C4—C5—C6	−0.6 (3)	C49—C50—C51—C52	13.8 (3)
C9—C10—C11—C12	159.3 (2)	C49—C50—C51—C56	−169.6 (2)
C10—C1—C2—C3	−3.4 (3)	C49—C50—C63—C64	−77.4 (3)
C10—C11—C12—C13	0.4 (3)	C49—C50—C63—C68	103.1 (3)
C11—C12—C13—O1	36.2 (3)	C50—O2—C38—C39	149.5 (2)
C11—C12—C13—C14	152.9 (2)	C50—O2—C38—C47	−32.9 (3)
C11—C12—C13—C26	−82.7 (3)	C50—C51—C52—C53	176.2 (2)
C12—C13—C14—C15	−90.3 (3)	C50—C51—C56—C55	−176.3 (2)
C12—C13—C14—C19	87.1 (3)	C50—C63—C64—C65	−177.2 (2)
C12—C13—C26—C27	−9.3 (3)	C50—C63—C68—C67	177.0 (2)
C12—C13—C26—C31	175.1 (2)	C51—C50—C63—C64	48.5 (3)
C13—O1—C1—C2	−145.0 (2)	C51—C50—C63—C68	−130.9 (2)
C13—O1—C1—C10	37.2 (3)	C51—C52—C53—C54	−0.2 (3)
C13—C14—C15—C16	178.7 (2)	C52—C51—C56—C55	0.5 (3)
C13—C14—C19—C18	−178.2 (2)	C52—C53—C54—C55	0.8 (3)
C13—C26—C27—C28	−173.4 (2)	C52—C53—C54—C57	−179.8 (2)
C13—C26—C31—C30	172.6 (2)	C53—C54—C55—C56	−0.8 (3)
C14—C13—C26—C27	115.3 (2)	C53—C54—C57—C58	−38.5 (3)
C14—C13—C26—C31	−60.4 (3)	C53—C54—C57—C62	142.9 (3)
C14—C15—C16—C17	−1.6 (4)	C54—C55—C56—C51	0.1 (3)
C15—C14—C19—C18	−0.7 (4)	C54—C57—C58—C59	−178.2 (2)
C15—C16—C17—C18	1.0 (4)	C54—C57—C62—C61	177.8 (3)
C15—C16—C17—C20	179.2 (2)	C55—C54—C57—C58	140.9 (3)
C16—C17—C18—C19	−0.3 (4)	C55—C54—C57—C62	−37.7 (4)
C16—C17—C20—C21	22.1 (4)	C56—C51—C52—C53	−0.5 (3)
C16—C17—C20—C25	−155.7 (3)	C57—C54—C55—C56	179.8 (2)
C17—C18—C19—C14	0.2 (4)	C57—C58—C59—C60	0.2 (4)
C17—C20—C21—C22	179.2 (3)	C58—C57—C62—C61	−0.8 (4)
C17—C20—C25—C24	−179.2 (3)	C58—C59—C60—C61	−0.6 (5)
C18—C17—C20—C21	−159.8 (3)	C59—C60—C61—C62	0.3 (5)
C18—C17—C20—C25	22.5 (4)	C60—C61—C62—C57	0.5 (5)
C19—C14—C15—C16	1.4 (4)	C62—C57—C58—C59	0.5 (4)
C20—C17—C18—C19	−178.6 (2)	C63—C50—C51—C52	−111.2 (2)
C20—C21—C22—C23	2.1 (5)	C63—C50—C51—C56	65.5 (3)
C21—C20—C25—C24	2.9 (4)	C63—C64—C65—C66	−0.3 (4)
C21—C22—C23—C24	−1.2 (5)	C64—C63—C68—C67	−2.5 (4)
C22—C23—C24—C25	1.2 (5)	C64—C65—C66—C67	−1.4 (4)
C23—C24—C25—C20	−2.1 (5)	C64—C65—C66—C69	176.2 (2)
C25—C20—C21—C22	−2.9 (4)	C65—C66—C67—C68	1.1 (4)
C26—C13—C14—C15	143.3 (2)	C65—C66—C69—C70	−33.4 (4)
C26—C13—C14—C19	−39.3 (3)	C65—C66—C69—C74	145.6 (3)
C26—C27—C28—C29	1.0 (4)	C66—C67—C68—C63	0.8 (4)
C27—C26—C31—C30	−3.3 (3)	C66—C69—C70—C71	−179.0 (2)
C27—C28—C29—C30	−3.1 (3)	C66—C69—C74—C73	179.7 (3)
C27—C28—C29—C32	173.8 (2)	C67—C66—C69—C70	144.1 (3)
C28—C29—C30—C31	2.0 (3)	C67—C66—C69—C74	−36.8 (4)
C28—C29—C32—C33	46.3 (3)	C68—C63—C64—C65	2.2 (4)
C28—C29—C32—C37	−130.9 (3)	C69—C66—C67—C68	−176.5 (2)
C29—C30—C31—C26	1.2 (4)	C69—C70—C71—C72	−0.9 (4)
C29—C32—C33—C34	−175.8 (2)	C70—C69—C74—C73	−1.2 (4)
C29—C32—C37—C36	175.4 (2)	C70—C71—C72—C73	−0.9 (5)
C30—C29—C32—C33	−136.9 (3)	C71—C72—C73—C74	1.5 (5)
C30—C29—C32—C37	45.9 (3)	C72—C73—C74—C69	−0.5 (5)
C31—C26—C27—C28	2.2 (3)	C74—C69—C70—C71	1.9 (4)