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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.
Supporting information
CCDC references: 921591; 910430
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)-3
H-naphtho[2,1-
b]pyran (NP1)
top
Crystal data top
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) Å3 | 0.2 × 0.18 × 0.12 mm |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.036P)2] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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)-3
H-naphtho[2,1-
b]pyran (NP2)
top
Crystal data top
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) Å3 | Prism, colorless |
Z = 8 | 0.2 × 0.18 × 0.14 mm |
Data collection top
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 top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.067 | w = 1/[σ2(Fo2) + (0.0853P)2 + 0.2747P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0050 (6) |
Special details top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) |
Geometrical parameters (Å, °) of the C—H···C interactions in NP1 topC—H···C interaction | H···C length | vdW distancea | Angle |
C6—H6···C26 | 2.865 | -0.035 | 147.6 |
C32—H32···C2 | 2.760 | -0.140 | 148.21 |
C2—H2···C23 | 2.782 | -0.118 | 140.52 |
C3—H3···C18 | 2.874 | -0.026 | 140.62 |
C17—H17···C30 | 2.799 | -0.101 | 162.9 |
Note: (a) the sum of the van der Waals (vdW) radii of corresponding
atoms. |
Geometrical parameters (Å, °) of C—H···X interactions in NP2 topC—H···X interaction | H···X length | vdW distancea | Angle |
C62—H62···C23 | 2.860 | -0.040 | 124.6 |
C6—H6···C29 | 2.875 | -0.025 | 157.2 |
C31—H31···O2 | 2.714 | -0.006 | 155.3 |
C56—H56···O1 | 2.588 | -0.132 | 149.2 |
Note: (a) the sum of the van der Waals (vdW) radii of corresponding
atoms. |
Maximum absorption wavelength (nm) of NP1–NP4 after irradiation
in different media topCompound | λmax | | |
| Toluene | Ethyl acetate | Absolute ethanol |
NP1 | 441 | 445 | 457 |
NP2 | 446 | 448 | 461 |
NP3 | 451 | 454 | 477 |
NP4 | 469 | 474 | 488 |
Absorbance (Abs) at the photostationary state, half-life (T1/2) of
decolorization and kinetic parameters (k1 and k2) topSolvent | Compound | Abs | T1/2 (s) | k1 (× 10-3, s-1) | k2 (× 10-3, s-1) |
Toluene | NP1 | 2.646 | 349 | 6.4 (0.03)a | 0.078 (0.50)a |
| NP2 | 0.523 | 11 | 80 (0.04)a | – |
| NP3 | 0.505 | 10 | 106 (0.04)a | 1.96 (0.65)a |
| NP4 | 2.767 | 105 | 9.14 (0.32)a | – |
Ethyl acetate | NP1 | 2.686 | 367 | 3.1 (0.37)a | – |
| NP2 | 0.557 | 13 | 76 (0.00)a | – |
| NP3 | 0.516 | 9 | 106 (0.09)a | – |
| NP4 | 2.828 | 117 | 9.14 (0.50)a | – |
Absolute ethanol | NP1 | 2.269 | 506 | 1.77 (1.83)a | – |
| NP2 | 0.512 | 17 | 51.4 (0.14)a | – |
| NP3 | 0.439 | 9 | 113 (0.08)a | – |
| NP4 | 2.620 | 232 | 4.15 (0.94)a | – |
Note: (a) the standard error calculated by Origin software. |
Maximum absorption wavelength (nm) of NP1–NP4 in PMMA film topCompound | NP1 | NP2 | NP3 | NP4 |
λmax | 473 | 475 | 478 | 528 |
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