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Isostructurality is more likely to occur in multicomponent systems. In this context, three closely related solvates were crystallized, namely, benzene (C
27H
21BrO
6·C
6H
6), toluene (C
27H
21BrO
6·C
7H
8) and xylene (C
27H
21BrO
6·C
8H
10) with methyl 3a-acetyl-3-(4-bromophenyl)-4-oxo-1-phenyl-3,3a,4,9b-tetrahydro-1
H-furo[3,4-
c]chromene-1-carboxylate, and their crystal structures determined. All three structures belong to the same space group (
P) and display similar unit-cell dimensions and conformations, as well as isostructural crystal packings. The isostructurality is confirmed by unit-cell and isostructural similarity indices. In each solvate, weak C—H
O and C—H
π interactions extend the molecules into two-dimensional networks, which are further linked by C—H
Br and Br
Br interactions into three-dimensional networks. The conformation of the core molecule is predominantly responsible for governing the isostructurality.
Supporting information
CCDC references: 1544953; 1544952; 1544951
For all compounds, data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2005) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).
(Ia) Methyl 3a-acetyl-3-(4-bromophenyl)-4-oxo-1-phenyl-3,3a,4,9b-tetrahydro-1
H-furo[3,4-
c]chromene-1-carboxylate benzene monosolvate
top
Crystal data top
C27H21BrO6·C6H6 | Z = 2 |
Mr = 599.45 | F(000) = 616 |
Triclinic, P1 | Dx = 1.404 Mg m−3 |
a = 8.4269 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.4905 (8) Å | Cell parameters from 5828 reflections |
c = 15.1415 (10) Å | θ = 2.5–27.0° |
α = 66.530 (1)° | µ = 1.49 mm−1 |
β = 76.005 (1)° | T = 294 K |
γ = 85.473 (1)° | Block, colourless |
V = 1418.22 (17) Å3 | 0.19 × 0.17 × 0.09 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 4034 reflections with I > 2σ(I) |
ω scans | Rint = 0.021 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 25.0°, θmin = 1.8° |
Tmin = 0.73, Tmax = 0.86 | h = −10→10 |
13730 measured reflections | k = −14→14 |
4968 independent reflections | l = −17→17 |
Refinement top
Refinement on F2 | 84 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0527P)2 + 0.2175P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
4968 reflections | Δρmax = 0.18 e Å−3 |
394 parameters | Δρmin = −0.43 e Å−3 |
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 | Occ. (<1) |
Br1 | 0.71066 (4) | 0.03317 (2) | 0.02574 (2) | 0.08946 (14) | |
C1 | 0.3530 (2) | 0.32188 (15) | 0.25923 (13) | 0.0411 (4) | |
H1 | 0.3116 | 0.2695 | 0.3284 | 0.049* | |
C2 | 0.4685 (2) | 0.41756 (15) | 0.25658 (12) | 0.0392 (4) | |
C3 | 0.3672 (2) | 0.52833 (15) | 0.22766 (13) | 0.0391 (4) | |
H3 | 0.4006 | 0.5670 | 0.1554 | 0.047* | |
C4 | 0.1907 (2) | 0.48226 (15) | 0.25115 (13) | 0.0400 (4) | |
C5 | 0.4286 (2) | 0.24895 (15) | 0.20183 (13) | 0.0410 (4) | |
C6 | 0.4169 (2) | 0.27581 (17) | 0.10605 (14) | 0.0502 (5) | |
H6 | 0.3550 | 0.3390 | 0.0761 | 0.060* | |
C7 | 0.4956 (3) | 0.21056 (18) | 0.05407 (15) | 0.0557 (5) | |
H7 | 0.4848 | 0.2281 | −0.0099 | 0.067* | |
C8 | 0.5906 (3) | 0.11898 (17) | 0.09802 (16) | 0.0533 (5) | |
C9 | 0.6021 (3) | 0.08925 (18) | 0.19359 (17) | 0.0585 (5) | |
H9 | 0.6650 | 0.0265 | 0.2230 | 0.070* | |
C10 | 0.5196 (3) | 0.15328 (17) | 0.24564 (15) | 0.0529 (5) | |
H10 | 0.5250 | 0.1322 | 0.3111 | 0.064* | |
C11 | 0.6311 (2) | 0.43505 (16) | 0.17643 (14) | 0.0433 (4) | |
C12 | 0.7808 (2) | 0.3763 (2) | 0.20661 (18) | 0.0632 (6) | |
H12A | 0.8713 | 0.3983 | 0.1500 | 0.095* | |
H12B | 0.7638 | 0.2933 | 0.2338 | 0.095* | |
H12C | 0.8040 | 0.3995 | 0.2556 | 0.095* | |
C13 | 0.5078 (2) | 0.38161 (17) | 0.35695 (14) | 0.0463 (4) | |
C14 | 0.4924 (2) | 0.58193 (17) | 0.33889 (13) | 0.0458 (4) | |
C15 | 0.5353 (2) | 0.6593 (2) | 0.37419 (15) | 0.0547 (5) | |
H15 | 0.5958 | 0.6348 | 0.4224 | 0.066* | |
C16 | 0.4869 (3) | 0.7730 (2) | 0.33668 (17) | 0.0620 (6) | |
H16 | 0.5139 | 0.8259 | 0.3601 | 0.074* | |
C17 | 0.3986 (3) | 0.80925 (19) | 0.26454 (18) | 0.0623 (6) | |
H17 | 0.3662 | 0.8864 | 0.2394 | 0.075* | |
C18 | 0.3580 (2) | 0.73048 (17) | 0.22958 (16) | 0.0528 (5) | |
H18 | 0.2995 | 0.7556 | 0.1803 | 0.063* | |
C19 | 0.4035 (2) | 0.61427 (16) | 0.26715 (13) | 0.0428 (4) | |
C20 | 0.1118 (2) | 0.43328 (16) | 0.36296 (14) | 0.0431 (4) | |
C21 | −0.1229 (3) | 0.3376 (2) | 0.48447 (15) | 0.0646 (6) | |
H21A | −0.0622 | 0.2731 | 0.5199 | 0.097* | |
H21B | −0.2288 | 0.3103 | 0.4885 | 0.097* | |
H21C | −0.1353 | 0.3948 | 0.5131 | 0.097* | |
C22 | 0.0860 (2) | 0.57072 (16) | 0.18908 (13) | 0.0416 (4) | |
C23 | −0.0302 (2) | 0.63540 (18) | 0.22736 (15) | 0.0540 (5) | |
H23 | −0.0490 | 0.6225 | 0.2939 | 0.065* | |
C24 | −0.1181 (3) | 0.71878 (19) | 0.16770 (17) | 0.0645 (6) | |
H24 | −0.1953 | 0.7618 | 0.1943 | 0.077* | |
C25 | −0.0926 (3) | 0.7386 (2) | 0.06993 (18) | 0.0693 (6) | |
H25 | −0.1537 | 0.7937 | 0.0302 | 0.083* | |
C26 | 0.0239 (3) | 0.6763 (2) | 0.03084 (18) | 0.0741 (7) | |
H26 | 0.0434 | 0.6906 | −0.0361 | 0.089* | |
C27 | 0.1126 (3) | 0.59251 (19) | 0.09005 (15) | 0.0575 (5) | |
H27 | 0.1908 | 0.5506 | 0.0628 | 0.069* | |
O1 | 0.21818 (14) | 0.38523 (10) | 0.22171 (9) | 0.0419 (3) | |
O2 | 0.54167 (16) | 0.46704 (12) | 0.38354 (9) | 0.0509 (3) | |
O3 | 0.52138 (19) | 0.28245 (13) | 0.41112 (10) | 0.0609 (4) | |
O4 | 0.17949 (18) | 0.42882 (15) | 0.42482 (10) | 0.0649 (4) | |
O5 | −0.03573 (16) | 0.38974 (14) | 0.38158 (10) | 0.0576 (4) | |
O6 | 0.63060 (18) | 0.49466 (14) | 0.09211 (11) | 0.0659 (4) | |
C28 | −0.0169 (9) | 0.1041 (4) | 0.3275 (7) | 0.115 (3) | 0.683 (13) |
H28 | 0.0253 | 0.1771 | 0.3136 | 0.138* | 0.683 (13) |
C29 | 0.0485 (6) | 0.0448 (7) | 0.2668 (4) | 0.142 (3) | 0.683 (13) |
H29 | 0.1346 | 0.0781 | 0.2123 | 0.170* | 0.683 (13) |
C30 | −0.0147 (8) | −0.0643 (7) | 0.2875 (7) | 0.134 (3) | 0.683 (13) |
H30 | 0.0291 | −0.1040 | 0.2469 | 0.161* | 0.683 (13) |
C31 | −0.1434 (9) | −0.1141 (3) | 0.3690 (8) | 0.111 (3) | 0.683 (13) |
H31 | −0.1857 | −0.1871 | 0.3828 | 0.133* | 0.683 (13) |
C32 | −0.2088 (6) | −0.0548 (8) | 0.4297 (4) | 0.123 (3) | 0.683 (13) |
H32 | −0.2949 | −0.0881 | 0.4842 | 0.148* | 0.683 (13) |
C33 | −0.1456 (9) | 0.0543 (8) | 0.4090 (6) | 0.132 (3) | 0.683 (13) |
H33 | −0.1894 | 0.0940 | 0.4496 | 0.158* | 0.683 (13) |
C281 | 0.0176 (17) | 0.0924 (11) | 0.2812 (11) | 0.106 (5) | 0.317 (13) |
H281 | 0.0848 | 0.1560 | 0.2368 | 0.128* | 0.317 (13) |
C291 | 0.0160 (16) | −0.0066 (15) | 0.2609 (6) | 0.115 (6) | 0.317 (13) |
H291 | 0.0822 | −0.0093 | 0.2030 | 0.138* | 0.317 (13) |
C301 | −0.084 (2) | −0.1017 (8) | 0.3272 (9) | 0.089 (5) | 0.317 (13) |
H301 | −0.0855 | −0.1680 | 0.3136 | 0.106* | 0.317 (13) |
C311 | −0.1833 (17) | −0.0977 (10) | 0.4137 (7) | 0.087 (5) | 0.317 (13) |
H311 | −0.2505 | −0.1612 | 0.4581 | 0.104* | 0.317 (13) |
C321 | −0.1817 (17) | 0.0014 (14) | 0.4340 (8) | 0.110 (5) | 0.317 (13) |
H321 | −0.2479 | 0.0041 | 0.4919 | 0.132* | 0.317 (13) |
C331 | −0.081 (2) | 0.0965 (7) | 0.3677 (13) | 0.109 (6) | 0.317 (13) |
H331 | −0.0802 | 0.1627 | 0.3813 | 0.131* | 0.317 (13) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.1075 (2) | 0.06487 (19) | 0.0935 (2) | 0.02903 (15) | −0.00588 (16) | −0.04336 (16) |
C1 | 0.0437 (10) | 0.0374 (9) | 0.0375 (9) | 0.0005 (7) | −0.0087 (7) | −0.0103 (8) |
C2 | 0.0418 (9) | 0.0399 (9) | 0.0348 (9) | 0.0012 (7) | −0.0083 (7) | −0.0140 (7) |
C3 | 0.0399 (9) | 0.0394 (9) | 0.0355 (9) | 0.0007 (7) | −0.0045 (7) | −0.0145 (7) |
C4 | 0.0404 (9) | 0.0410 (9) | 0.0388 (9) | 0.0003 (7) | −0.0044 (7) | −0.0183 (8) |
C5 | 0.0443 (10) | 0.0323 (9) | 0.0433 (10) | −0.0007 (7) | −0.0112 (8) | −0.0108 (8) |
C6 | 0.0582 (12) | 0.0414 (10) | 0.0474 (11) | 0.0139 (9) | −0.0150 (9) | −0.0146 (9) |
C7 | 0.0666 (13) | 0.0509 (12) | 0.0486 (11) | 0.0107 (10) | −0.0118 (10) | −0.0211 (9) |
C8 | 0.0576 (12) | 0.0368 (10) | 0.0634 (13) | 0.0044 (9) | −0.0073 (10) | −0.0219 (9) |
C9 | 0.0622 (13) | 0.0397 (11) | 0.0753 (15) | 0.0152 (9) | −0.0258 (11) | −0.0212 (10) |
C10 | 0.0650 (12) | 0.0425 (11) | 0.0529 (11) | 0.0082 (9) | −0.0242 (10) | −0.0155 (9) |
C11 | 0.0426 (10) | 0.0444 (10) | 0.0453 (11) | −0.0001 (8) | −0.0070 (8) | −0.0216 (9) |
C12 | 0.0445 (11) | 0.0815 (16) | 0.0688 (14) | 0.0086 (10) | −0.0110 (10) | −0.0372 (12) |
C13 | 0.0466 (10) | 0.0520 (12) | 0.0397 (10) | 0.0002 (9) | −0.0089 (8) | −0.0176 (9) |
C14 | 0.0443 (10) | 0.0515 (11) | 0.0382 (10) | −0.0066 (8) | 0.0013 (8) | −0.0189 (9) |
C15 | 0.0521 (11) | 0.0681 (14) | 0.0457 (11) | −0.0155 (10) | 0.0009 (9) | −0.0281 (10) |
C16 | 0.0614 (13) | 0.0640 (14) | 0.0665 (14) | −0.0170 (11) | 0.0031 (11) | −0.0386 (12) |
C17 | 0.0603 (13) | 0.0466 (12) | 0.0776 (15) | −0.0073 (10) | 0.0005 (11) | −0.0297 (11) |
C18 | 0.0503 (11) | 0.0472 (11) | 0.0585 (12) | −0.0028 (9) | −0.0064 (9) | −0.0211 (10) |
C19 | 0.0390 (9) | 0.0445 (10) | 0.0421 (10) | −0.0051 (8) | 0.0015 (8) | −0.0193 (8) |
C20 | 0.0396 (10) | 0.0448 (10) | 0.0432 (10) | 0.0012 (8) | −0.0051 (8) | −0.0179 (8) |
C21 | 0.0486 (12) | 0.0826 (16) | 0.0467 (12) | −0.0088 (11) | 0.0020 (9) | −0.0145 (11) |
C22 | 0.0390 (9) | 0.0425 (10) | 0.0428 (10) | 0.0015 (7) | −0.0061 (8) | −0.0183 (8) |
C23 | 0.0575 (12) | 0.0532 (12) | 0.0477 (11) | 0.0092 (9) | −0.0037 (9) | −0.0225 (9) |
C24 | 0.0583 (13) | 0.0568 (13) | 0.0704 (15) | 0.0193 (10) | −0.0050 (11) | −0.0255 (11) |
C25 | 0.0734 (15) | 0.0631 (14) | 0.0705 (15) | 0.0248 (12) | −0.0283 (12) | −0.0228 (12) |
C26 | 0.0976 (18) | 0.0767 (16) | 0.0536 (13) | 0.0312 (14) | −0.0296 (13) | −0.0297 (12) |
C27 | 0.0649 (13) | 0.0607 (13) | 0.0501 (12) | 0.0212 (10) | −0.0145 (10) | −0.0277 (10) |
O1 | 0.0398 (6) | 0.0417 (7) | 0.0478 (7) | 0.0043 (5) | −0.0113 (5) | −0.0211 (6) |
O2 | 0.0604 (8) | 0.0541 (8) | 0.0414 (7) | −0.0021 (6) | −0.0151 (6) | −0.0193 (6) |
O3 | 0.0818 (10) | 0.0513 (9) | 0.0492 (8) | 0.0060 (7) | −0.0276 (7) | −0.0131 (7) |
O4 | 0.0581 (9) | 0.0927 (12) | 0.0432 (8) | −0.0203 (8) | −0.0051 (7) | −0.0257 (8) |
O5 | 0.0430 (8) | 0.0774 (10) | 0.0428 (7) | −0.0120 (7) | −0.0042 (6) | −0.0144 (7) |
O6 | 0.0600 (9) | 0.0755 (10) | 0.0434 (8) | 0.0077 (7) | 0.0021 (6) | −0.0130 (8) |
C28 | 0.082 (6) | 0.081 (4) | 0.182 (10) | −0.003 (3) | −0.047 (6) | −0.041 (5) |
C29 | 0.081 (4) | 0.067 (6) | 0.263 (8) | 0.006 (4) | −0.033 (4) | −0.055 (5) |
C30 | 0.076 (5) | 0.071 (6) | 0.251 (10) | 0.007 (4) | −0.054 (5) | −0.049 (7) |
C31 | 0.086 (6) | 0.072 (4) | 0.169 (9) | 0.000 (3) | −0.072 (6) | −0.016 (5) |
C32 | 0.148 (6) | 0.069 (7) | 0.146 (6) | −0.017 (5) | −0.078 (4) | −0.007 (4) |
C33 | 0.157 (8) | 0.078 (7) | 0.159 (8) | −0.026 (5) | −0.073 (6) | −0.019 (6) |
C281 | 0.083 (9) | 0.070 (9) | 0.169 (13) | 0.007 (7) | −0.049 (8) | −0.039 (8) |
C291 | 0.095 (10) | 0.073 (13) | 0.143 (9) | 0.019 (8) | −0.025 (7) | −0.013 (8) |
C301 | 0.082 (13) | 0.060 (7) | 0.108 (9) | −0.008 (6) | −0.017 (7) | −0.018 (6) |
C311 | 0.138 (11) | 0.052 (8) | 0.076 (7) | −0.006 (8) | −0.044 (6) | −0.020 (6) |
C321 | 0.143 (13) | 0.067 (13) | 0.122 (10) | −0.012 (9) | −0.047 (7) | −0.026 (10) |
C331 | 0.111 (17) | 0.054 (7) | 0.143 (13) | −0.013 (7) | −0.037 (10) | −0.010 (8) |
Geometric parameters (Å, º) top
Br1—C8 | 1.897 (2) | C20—O4 | 1.191 (2) |
C1—O1 | 1.432 (2) | C20—O5 | 1.318 (2) |
C1—C5 | 1.504 (2) | C21—O5 | 1.451 (2) |
C1—C2 | 1.582 (2) | C21—H21A | 0.9600 |
C1—H1 | 0.9800 | C21—H21B | 0.9600 |
C2—C13 | 1.516 (2) | C21—H21C | 0.9600 |
C2—C3 | 1.532 (2) | C22—C27 | 1.376 (3) |
C2—C11 | 1.559 (2) | C22—C23 | 1.386 (3) |
C3—C19 | 1.501 (2) | C23—C24 | 1.379 (3) |
C3—C4 | 1.545 (2) | C23—H23 | 0.9300 |
C3—H3 | 0.9800 | C24—C25 | 1.364 (3) |
C4—O1 | 1.434 (2) | C24—H24 | 0.9300 |
C4—C22 | 1.518 (3) | C25—C26 | 1.373 (3) |
C4—C20 | 1.542 (2) | C25—H25 | 0.9300 |
C5—C6 | 1.379 (3) | C26—C27 | 1.382 (3) |
C5—C10 | 1.388 (3) | C26—H26 | 0.9300 |
C6—C7 | 1.377 (3) | C27—H27 | 0.9300 |
C6—H6 | 0.9300 | C28—C29 | 1.3900 |
C7—C8 | 1.378 (3) | C28—C33 | 1.3900 |
C7—H7 | 0.9300 | C28—H28 | 0.9300 |
C8—C9 | 1.370 (3) | C29—C30 | 1.3900 |
C9—C10 | 1.376 (3) | C29—H29 | 0.9300 |
C9—H9 | 0.9300 | C30—C31 | 1.3900 |
C10—H10 | 0.9300 | C30—H30 | 0.9300 |
C11—O6 | 1.196 (2) | C31—C32 | 1.3900 |
C11—C12 | 1.484 (3) | C31—H31 | 0.9300 |
C12—H12A | 0.9600 | C32—C33 | 1.3900 |
C12—H12B | 0.9600 | C32—H32 | 0.9300 |
C12—H12C | 0.9600 | C33—H33 | 0.9300 |
C13—O3 | 1.197 (2) | C281—C291 | 1.3900 |
C13—O2 | 1.352 (2) | C281—C331 | 1.3900 |
C14—C19 | 1.379 (3) | C281—H281 | 0.9300 |
C14—C15 | 1.382 (3) | C291—C301 | 1.3900 |
C14—O2 | 1.399 (2) | C291—H291 | 0.9300 |
C15—C16 | 1.373 (3) | C301—C311 | 1.3900 |
C15—H15 | 0.9300 | C301—H301 | 0.9300 |
C16—C17 | 1.378 (3) | C311—C321 | 1.3900 |
C16—H16 | 0.9300 | C311—H311 | 0.9300 |
C17—C18 | 1.386 (3) | C321—C331 | 1.3900 |
C17—H17 | 0.9300 | C321—H321 | 0.9300 |
C18—C19 | 1.392 (3) | C331—H331 | 0.9300 |
C18—H18 | 0.9300 | | |
| | | |
O1—C1—C5 | 110.25 (14) | C14—C19—C18 | 117.21 (18) |
O1—C1—C2 | 105.07 (13) | C14—C19—C3 | 120.66 (17) |
C5—C1—C2 | 116.28 (14) | C18—C19—C3 | 122.03 (17) |
O1—C1—H1 | 108.3 | O4—C20—O5 | 124.38 (17) |
C5—C1—H1 | 108.3 | O4—C20—C4 | 124.23 (16) |
C2—C1—H1 | 108.3 | O5—C20—C4 | 111.23 (15) |
C13—C2—C3 | 113.78 (15) | O5—C21—H21A | 109.5 |
C13—C2—C11 | 109.17 (14) | O5—C21—H21B | 109.5 |
C3—C2—C11 | 109.63 (14) | H21A—C21—H21B | 109.5 |
C13—C2—C1 | 109.66 (14) | O5—C21—H21C | 109.5 |
C3—C2—C1 | 102.89 (13) | H21A—C21—H21C | 109.5 |
C11—C2—C1 | 111.64 (14) | H21B—C21—H21C | 109.5 |
C19—C3—C2 | 113.31 (14) | C27—C22—C23 | 118.47 (18) |
C19—C3—C4 | 120.39 (14) | C27—C22—C4 | 119.21 (16) |
C2—C3—C4 | 104.05 (14) | C23—C22—C4 | 122.22 (16) |
C19—C3—H3 | 106.0 | C24—C23—C22 | 120.67 (19) |
C2—C3—H3 | 106.0 | C24—C23—H23 | 119.7 |
C4—C3—H3 | 106.0 | C22—C23—H23 | 119.7 |
O1—C4—C22 | 109.31 (13) | C25—C24—C23 | 120.5 (2) |
O1—C4—C20 | 107.27 (14) | C25—C24—H24 | 119.8 |
C22—C4—C20 | 113.46 (14) | C23—C24—H24 | 119.8 |
O1—C4—C3 | 101.38 (13) | C24—C25—C26 | 119.4 (2) |
C22—C4—C3 | 112.24 (14) | C24—C25—H25 | 120.3 |
C20—C4—C3 | 112.32 (14) | C26—C25—H25 | 120.3 |
C6—C5—C10 | 118.55 (18) | C25—C26—C27 | 120.6 (2) |
C6—C5—C1 | 122.80 (16) | C25—C26—H26 | 119.7 |
C10—C5—C1 | 118.59 (16) | C27—C26—H26 | 119.7 |
C7—C6—C5 | 121.02 (18) | C22—C27—C26 | 120.4 (2) |
C7—C6—H6 | 119.5 | C22—C27—H27 | 119.8 |
C5—C6—H6 | 119.5 | C26—C27—H27 | 119.8 |
C6—C7—C8 | 119.16 (19) | C1—O1—C4 | 107.60 (12) |
C6—C7—H7 | 120.4 | C13—O2—C14 | 121.68 (14) |
C8—C7—H7 | 120.4 | C20—O5—C21 | 117.18 (15) |
C9—C8—C7 | 120.98 (19) | C29—C28—C33 | 120.0 |
C9—C8—Br1 | 118.83 (15) | C29—C28—H28 | 120.0 |
C7—C8—Br1 | 120.18 (16) | C33—C28—H28 | 120.0 |
C8—C9—C10 | 119.30 (18) | C28—C29—C30 | 120.0 |
C8—C9—H9 | 120.3 | C28—C29—H29 | 120.0 |
C10—C9—H9 | 120.3 | C30—C29—H29 | 120.0 |
C9—C10—C5 | 120.92 (19) | C31—C30—C29 | 120.0 |
C9—C10—H10 | 119.5 | C31—C30—H30 | 120.0 |
C5—C10—H10 | 119.5 | C29—C30—H30 | 120.0 |
O6—C11—C12 | 122.06 (18) | C30—C31—C32 | 120.0 |
O6—C11—C2 | 118.66 (16) | C30—C31—H31 | 120.0 |
C12—C11—C2 | 119.27 (17) | C32—C31—H31 | 120.0 |
C11—C12—H12A | 109.5 | C33—C32—C31 | 120.0 |
C11—C12—H12B | 109.5 | C33—C32—H32 | 120.0 |
H12A—C12—H12B | 109.5 | C31—C32—H32 | 120.0 |
C11—C12—H12C | 109.5 | C32—C33—C28 | 120.0 |
H12A—C12—H12C | 109.5 | C32—C33—H33 | 120.0 |
H12B—C12—H12C | 109.5 | C28—C33—H33 | 120.0 |
O3—C13—O2 | 117.98 (16) | C291—C281—C331 | 120.0 |
O3—C13—C2 | 124.01 (17) | C291—C281—H281 | 120.0 |
O2—C13—C2 | 117.81 (16) | C331—C281—H281 | 120.0 |
C19—C14—C15 | 122.76 (19) | C301—C291—C281 | 120.0 |
C19—C14—O2 | 122.25 (16) | C301—C291—H291 | 120.0 |
C15—C14—O2 | 114.97 (17) | C281—C291—H291 | 120.0 |
C16—C15—C14 | 118.7 (2) | C311—C301—C291 | 120.0 |
C16—C15—H15 | 120.6 | C311—C301—H301 | 120.0 |
C14—C15—H15 | 120.6 | C291—C301—H301 | 120.0 |
C15—C16—C17 | 120.5 (2) | C301—C311—C321 | 120.0 |
C15—C16—H16 | 119.8 | C301—C311—H311 | 120.0 |
C17—C16—H16 | 119.8 | C321—C311—H311 | 120.0 |
C16—C17—C18 | 119.9 (2) | C311—C321—C331 | 120.0 |
C16—C17—H17 | 120.1 | C311—C321—H321 | 120.0 |
C18—C17—H17 | 120.1 | C331—C321—H321 | 120.0 |
C17—C18—C19 | 121.0 (2) | C321—C331—C281 | 120.0 |
C17—C18—H18 | 119.5 | C321—C331—H331 | 120.0 |
C19—C18—H18 | 119.5 | C281—C331—H331 | 120.0 |
| | | |
O1—C1—C2—C13 | 128.41 (15) | C15—C14—C19—C3 | 176.90 (17) |
C5—C1—C2—C13 | −109.40 (17) | O2—C14—C19—C3 | −5.0 (3) |
O1—C1—C2—C3 | 7.02 (16) | C17—C18—C19—C14 | −1.1 (3) |
C5—C1—C2—C3 | 129.21 (15) | C17—C18—C19—C3 | −177.39 (17) |
O1—C1—C2—C11 | −110.47 (15) | C2—C3—C19—C14 | −13.0 (2) |
C5—C1—C2—C11 | 11.7 (2) | C4—C3—C19—C14 | 110.95 (19) |
C13—C2—C3—C19 | 32.6 (2) | C2—C3—C19—C18 | 163.17 (16) |
C11—C2—C3—C19 | −89.95 (17) | C4—C3—C19—C18 | −72.8 (2) |
C1—C2—C3—C19 | 151.15 (14) | O1—C4—C20—O4 | 109.0 (2) |
C13—C2—C3—C4 | −99.89 (16) | C22—C4—C20—O4 | −130.1 (2) |
C11—C2—C3—C4 | 137.55 (14) | C3—C4—C20—O4 | −1.5 (3) |
C1—C2—C3—C4 | 18.66 (16) | O1—C4—C20—O5 | −66.59 (19) |
C19—C3—C4—O1 | −166.38 (15) | C22—C4—C20—O5 | 54.2 (2) |
C2—C3—C4—O1 | −38.10 (16) | C3—C4—C20—O5 | −177.14 (15) |
C19—C3—C4—C22 | 77.1 (2) | O1—C4—C22—C27 | −39.2 (2) |
C2—C3—C4—C22 | −154.63 (14) | C20—C4—C22—C27 | −158.89 (17) |
C19—C3—C4—C20 | −52.2 (2) | C3—C4—C22—C27 | 72.4 (2) |
C2—C3—C4—C20 | 76.11 (17) | O1—C4—C22—C23 | 144.42 (17) |
O1—C1—C5—C6 | 24.8 (2) | C20—C4—C22—C23 | 24.7 (2) |
C2—C1—C5—C6 | −94.6 (2) | C3—C4—C22—C23 | −103.9 (2) |
O1—C1—C5—C10 | −157.95 (16) | C27—C22—C23—C24 | 0.7 (3) |
C2—C1—C5—C10 | 82.6 (2) | C4—C22—C23—C24 | 177.08 (19) |
C10—C5—C6—C7 | −0.9 (3) | C22—C23—C24—C25 | 0.3 (3) |
C1—C5—C6—C7 | 176.30 (18) | C23—C24—C25—C26 | −1.3 (4) |
C5—C6—C7—C8 | −1.7 (3) | C24—C25—C26—C27 | 1.3 (4) |
C6—C7—C8—C9 | 2.7 (3) | C23—C22—C27—C26 | −0.6 (3) |
C6—C7—C8—Br1 | −176.32 (16) | C4—C22—C27—C26 | −177.2 (2) |
C7—C8—C9—C10 | −1.1 (3) | C25—C26—C27—C22 | −0.4 (4) |
Br1—C8—C9—C10 | 177.95 (16) | C5—C1—O1—C4 | −158.87 (13) |
C8—C9—C10—C5 | −1.6 (3) | C2—C1—O1—C4 | −32.84 (16) |
C6—C5—C10—C9 | 2.6 (3) | C22—C4—O1—C1 | 163.27 (13) |
C1—C5—C10—C9 | −174.76 (18) | C20—C4—O1—C1 | −73.32 (16) |
C13—C2—C11—O6 | −158.34 (18) | C3—C4—O1—C1 | 44.61 (16) |
C3—C2—C11—O6 | −33.1 (2) | O3—C13—O2—C14 | −164.25 (17) |
C1—C2—C11—O6 | 80.3 (2) | C2—C13—O2—C14 | 20.6 (2) |
C13—C2—C11—C12 | 22.4 (2) | C19—C14—O2—C13 | 1.5 (3) |
C3—C2—C11—C12 | 147.69 (17) | C15—C14—O2—C13 | 179.74 (16) |
C1—C2—C11—C12 | −98.96 (19) | O4—C20—O5—C21 | 2.8 (3) |
C3—C2—C13—O3 | 147.57 (18) | C4—C20—O5—C21 | 178.36 (17) |
C11—C2—C13—O3 | −89.6 (2) | C33—C28—C29—C30 | 0.0 |
C1—C2—C13—O3 | 33.0 (2) | C28—C29—C30—C31 | 0.0 |
C3—C2—C13—O2 | −37.6 (2) | C29—C30—C31—C32 | 0.0 |
C11—C2—C13—O2 | 85.19 (19) | C30—C31—C32—C33 | 0.0 |
C1—C2—C13—O2 | −152.21 (15) | C31—C32—C33—C28 | 0.0 |
C19—C14—C15—C16 | 0.3 (3) | C29—C28—C33—C32 | 0.0 |
O2—C14—C15—C16 | −177.87 (17) | C331—C281—C291—C301 | 0.0 |
C14—C15—C16—C17 | −0.6 (3) | C281—C291—C301—C311 | 0.0 |
C15—C16—C17—C18 | 0.1 (3) | C291—C301—C311—C321 | 0.0 |
C16—C17—C18—C19 | 0.8 (3) | C301—C311—C321—C331 | 0.0 |
C15—C14—C19—C18 | 0.5 (3) | C311—C321—C331—C281 | 0.0 |
O2—C14—C19—C18 | 178.57 (16) | C291—C281—C331—C321 | 0.0 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O3 | 0.98 | 2.45 | 2.848 (2) | 104 |
C3—H3···O6 | 0.98 | 2.24 | 2.766 (2) | 113 |
C6—H6···O6i | 0.93 | 2.55 | 3.306 (2) | 139 |
C12—H12C···O5ii | 0.96 | 2.55 | 3.437 (3) | 153 |
C21—H21C···O4iii | 0.96 | 2.69 | 3.645 (3) | 174 |
C25—H25···Br1iv | 0.93 | 3.10 | 3.788 (2) | 132 |
C24—H24···Cg1v | 0.93 | 3.07 | 3.715 (2) | 128 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y, z; (iii) −x, −y+1, −z+1; (iv) x−1, y+1, z; (v) x−1, y, z. |
(Ib) Methyl 3a-acetyl-3-(4-bromophenyl)-4-oxo-1-phenyl-3,3a,4,9b-tetrahydro-1
H-furo[3,4-
c]chromene-1-carboxylate toluene monosolvate
top
Crystal data top
C27H21BrO6·C7H8 | Z = 2 |
Mr = 613.48 | F(000) = 632 |
Triclinic, P1 | Dx = 1.418 Mg m−3 |
a = 8.3989 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.5415 (7) Å | Cell parameters from 6899 reflections |
c = 15.2195 (8) Å | θ = 2.5–28.2° |
α = 67.408 (1)° | µ = 1.48 mm−1 |
β = 76.135 (1)° | T = 294 K |
γ = 85.458 (1)° | Block, colourless |
V = 1436.85 (14) Å3 | 0.15 × 0.14 × 0.08 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 4218 reflections with I > 2σ(I) |
ω scans | Rint = 0.025 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 25.0°, θmin = 1.8° |
Tmin = 0.81, Tmax = 0.87 | h = −9→9 |
13909 measured reflections | k = −14→14 |
5042 independent reflections | l = −18→18 |
Refinement top
Refinement on F2 | 44 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0656P)2 + 0.3104P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
5042 reflections | Δρmax = 0.31 e Å−3 |
414 parameters | Δρmin = −0.52 e Å−3 |
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 | Occ. (<1) |
Br1 | 0.70977 (4) | 0.53459 (2) | 0.02432 (2) | 0.08892 (15) | |
C1 | 0.3639 (2) | 0.82859 (16) | 0.25646 (13) | 0.0406 (4) | |
H1 | 0.3236 | 0.7773 | 0.3247 | 0.049* | |
C2 | 0.4789 (2) | 0.92385 (16) | 0.25442 (13) | 0.0391 (4) | |
C3 | 0.3749 (2) | 1.03263 (16) | 0.22863 (13) | 0.0386 (4) | |
H3 | 0.4071 | 1.0717 | 0.1574 | 0.046* | |
C4 | 0.1985 (2) | 0.98640 (16) | 0.25129 (13) | 0.0392 (4) | |
C5 | 0.4385 (2) | 0.75524 (15) | 0.19896 (13) | 0.0405 (4) | |
C6 | 0.4245 (3) | 0.78120 (18) | 0.10441 (15) | 0.0503 (5) | |
H6 | 0.3633 | 0.8444 | 0.0751 | 0.060* | |
C7 | 0.5005 (3) | 0.71413 (19) | 0.05281 (16) | 0.0554 (5) | |
H7 | 0.4888 | 0.7308 | −0.0103 | 0.067* | |
C8 | 0.5940 (3) | 0.62223 (18) | 0.09633 (17) | 0.0530 (5) | |
C9 | 0.6086 (3) | 0.59411 (18) | 0.19030 (18) | 0.0559 (5) | |
H9 | 0.6711 | 0.5314 | 0.2191 | 0.067* | |
C10 | 0.5293 (3) | 0.66029 (17) | 0.24162 (16) | 0.0508 (5) | |
H10 | 0.5369 | 0.6409 | 0.3059 | 0.061* | |
C11 | 0.6396 (2) | 0.94189 (17) | 0.17339 (14) | 0.0433 (4) | |
C12 | 0.7916 (3) | 0.8834 (2) | 0.20103 (18) | 0.0600 (6) | |
H12A | 0.8190 | 0.9080 | 0.2481 | 0.090* | |
H12B | 0.8800 | 0.9032 | 0.1440 | 0.090* | |
H12C | 0.7738 | 0.8013 | 0.2288 | 0.090* | |
C13 | 0.5209 (2) | 0.88773 (18) | 0.35312 (14) | 0.0451 (4) | |
C14 | 0.5003 (2) | 1.08466 (17) | 0.34062 (13) | 0.0443 (4) | |
C15 | 0.5419 (3) | 1.1612 (2) | 0.37770 (15) | 0.0516 (5) | |
H15 | 0.6028 | 1.1369 | 0.4254 | 0.062* | |
C16 | 0.4916 (3) | 1.2731 (2) | 0.34284 (17) | 0.0593 (6) | |
H16 | 0.5177 | 1.3252 | 0.3674 | 0.071* | |
C17 | 0.4025 (3) | 1.3093 (2) | 0.27152 (19) | 0.0615 (6) | |
H17 | 0.3689 | 1.3855 | 0.2481 | 0.074* | |
C18 | 0.3631 (3) | 1.23191 (18) | 0.23487 (16) | 0.0520 (5) | |
H18 | 0.3042 | 1.2571 | 0.1862 | 0.062* | |
C19 | 0.4103 (2) | 1.11717 (16) | 0.26971 (13) | 0.0415 (4) | |
C20 | 0.1205 (2) | 0.93700 (16) | 0.36169 (14) | 0.0418 (4) | |
C21 | −0.1135 (3) | 0.8449 (2) | 0.48247 (16) | 0.0624 (6) | |
H21A | −0.1325 | 0.9029 | 0.5103 | 0.094* | |
H21B | −0.0473 | 0.7851 | 0.5172 | 0.094* | |
H21C | −0.2166 | 0.8124 | 0.4874 | 0.094* | |
C22 | 0.0922 (2) | 1.07312 (16) | 0.19073 (14) | 0.0408 (4) | |
C23 | −0.0269 (3) | 1.13585 (18) | 0.22947 (16) | 0.0514 (5) | |
H23 | −0.0468 | 1.1228 | 0.2956 | 0.062* | |
C24 | −0.1166 (3) | 1.2175 (2) | 0.17097 (18) | 0.0610 (6) | |
H24 | −0.1965 | 1.2589 | 0.1980 | 0.073* | |
C25 | −0.0885 (3) | 1.2379 (2) | 0.07349 (19) | 0.0664 (6) | |
H25 | −0.1502 | 1.2920 | 0.0344 | 0.080* | |
C26 | 0.0320 (3) | 1.1777 (2) | 0.03385 (18) | 0.0693 (7) | |
H26 | 0.0530 | 1.1923 | −0.0326 | 0.083* | |
C27 | 0.1218 (3) | 1.09576 (19) | 0.09191 (15) | 0.0540 (5) | |
H27 | 0.2027 | 1.0555 | 0.0643 | 0.065* | |
O1 | 0.22721 (15) | 0.89039 (11) | 0.22049 (9) | 0.0421 (3) | |
O2 | 0.55257 (17) | 0.97151 (12) | 0.38210 (10) | 0.0490 (3) | |
O3 | 0.5385 (2) | 0.78954 (13) | 0.40401 (11) | 0.0607 (4) | |
O4 | 0.19142 (19) | 0.92986 (15) | 0.42306 (10) | 0.0623 (4) | |
O5 | −0.02914 (17) | 0.89652 (14) | 0.38036 (10) | 0.0554 (4) | |
O6 | 0.6354 (2) | 1.00079 (15) | 0.09091 (11) | 0.0655 (4) | |
C28 | −0.1630 (8) | 0.5160 (4) | 0.4190 (4) | 0.088 (2) | 0.596 (12) |
C29 | −0.1734 (9) | 0.4123 (3) | 0.4073 (5) | 0.097 (2) | 0.596 (12) |
H29 | −0.2411 | 0.3528 | 0.4555 | 0.117* | 0.596 (12) |
C30 | −0.0827 (12) | 0.3976 (6) | 0.3235 (7) | 0.111 (4) | 0.596 (12) |
H30 | −0.0896 | 0.3282 | 0.3157 | 0.133* | 0.596 (12) |
C31 | 0.0186 (10) | 0.4865 (9) | 0.2515 (5) | 0.159 (5) | 0.596 (12) |
H31 | 0.0793 | 0.4766 | 0.1955 | 0.190* | 0.596 (12) |
C32 | 0.0290 (8) | 0.5901 (8) | 0.2632 (4) | 0.204 (8) | 0.596 (12) |
H32 | 0.0967 | 0.6496 | 0.2150 | 0.245* | 0.596 (12) |
C33 | −0.0617 (9) | 0.6049 (4) | 0.3469 (5) | 0.082 (2) | 0.596 (12) |
H33 | −0.0548 | 0.6742 | 0.3548 | 0.099* | 0.596 (12) |
C34 | −0.2455 (16) | 0.5362 (11) | 0.5014 (8) | 0.152 (4) | 0.596 (12) |
H34A | −0.3576 | 0.5109 | 0.5185 | 0.229* | 0.596 (12) |
H34B | −0.2419 | 0.6174 | 0.4882 | 0.229* | 0.596 (12) |
H34C | −0.1943 | 0.4944 | 0.5546 | 0.229* | 0.596 (12) |
C281 | −0.1523 (15) | 0.4801 (14) | 0.4037 (7) | 0.148 (7) | 0.404 (12) |
C291 | −0.1161 (13) | 0.4042 (7) | 0.3552 (11) | 0.101 (4) | 0.404 (12) |
H291 | −0.1654 | 0.3313 | 0.3833 | 0.121* | 0.404 (12) |
C301 | −0.0062 (15) | 0.4372 (7) | 0.2648 (11) | 0.114 (4) | 0.404 (12) |
H301 | 0.0180 | 0.3863 | 0.2323 | 0.137* | 0.404 (12) |
C311 | 0.0674 (10) | 0.5461 (7) | 0.2228 (7) | 0.112 (4) | 0.404 (12) |
H311 | 0.1410 | 0.5682 | 0.1623 | 0.135* | 0.404 (12) |
C321 | 0.0312 (13) | 0.6221 (6) | 0.2713 (9) | 0.103 (4) | 0.404 (12) |
H321 | 0.0805 | 0.6950 | 0.2433 | 0.124* | 0.404 (12) |
C331 | −0.0787 (18) | 0.5891 (13) | 0.3618 (9) | 0.219 (17) | 0.404 (12) |
H331 | −0.1029 | 0.6399 | 0.3942 | 0.263* | 0.404 (12) |
C341 | −0.2644 (17) | 0.453 (2) | 0.4912 (10) | 0.184 (12) | 0.404 (12) |
H34D | −0.3427 | 0.3976 | 0.4962 | 0.276* | 0.404 (12) |
H34E | −0.3201 | 0.5212 | 0.4949 | 0.276* | 0.404 (12) |
H34F | −0.2090 | 0.4199 | 0.5438 | 0.276* | 0.404 (12) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.1072 (3) | 0.0690 (2) | 0.0940 (2) | 0.02882 (16) | −0.00750 (17) | −0.04884 (17) |
C1 | 0.0432 (10) | 0.0388 (10) | 0.0375 (9) | 0.0040 (8) | −0.0099 (8) | −0.0119 (8) |
C2 | 0.0416 (10) | 0.0404 (10) | 0.0356 (9) | 0.0044 (8) | −0.0098 (7) | −0.0149 (8) |
C3 | 0.0395 (9) | 0.0395 (9) | 0.0347 (9) | 0.0035 (7) | −0.0061 (7) | −0.0138 (7) |
C4 | 0.0398 (9) | 0.0402 (10) | 0.0402 (9) | 0.0029 (8) | −0.0072 (8) | −0.0194 (8) |
C5 | 0.0431 (10) | 0.0338 (9) | 0.0431 (10) | 0.0013 (8) | −0.0096 (8) | −0.0130 (8) |
C6 | 0.0586 (12) | 0.0438 (11) | 0.0459 (11) | 0.0133 (9) | −0.0143 (9) | −0.0152 (9) |
C7 | 0.0704 (14) | 0.0514 (12) | 0.0450 (11) | 0.0106 (10) | −0.0127 (10) | −0.0210 (9) |
C8 | 0.0558 (12) | 0.0395 (11) | 0.0637 (13) | 0.0061 (9) | −0.0072 (10) | −0.0244 (10) |
C9 | 0.0596 (13) | 0.0390 (11) | 0.0722 (15) | 0.0159 (9) | −0.0244 (11) | −0.0216 (10) |
C10 | 0.0600 (12) | 0.0416 (11) | 0.0518 (12) | 0.0080 (9) | −0.0229 (10) | −0.0141 (9) |
C11 | 0.0433 (10) | 0.0449 (11) | 0.0449 (11) | 0.0010 (8) | −0.0072 (8) | −0.0220 (9) |
C12 | 0.0429 (11) | 0.0757 (15) | 0.0686 (14) | 0.0094 (10) | −0.0132 (10) | −0.0364 (12) |
C13 | 0.0465 (11) | 0.0511 (12) | 0.0387 (10) | 0.0052 (9) | −0.0117 (8) | −0.0177 (9) |
C14 | 0.0425 (10) | 0.0501 (11) | 0.0377 (9) | −0.0037 (8) | −0.0004 (8) | −0.0183 (8) |
C15 | 0.0483 (11) | 0.0648 (14) | 0.0457 (11) | −0.0095 (10) | −0.0033 (9) | −0.0276 (10) |
C16 | 0.0584 (13) | 0.0616 (14) | 0.0655 (14) | −0.0120 (11) | −0.0007 (11) | −0.0376 (12) |
C17 | 0.0627 (14) | 0.0459 (12) | 0.0773 (16) | −0.0037 (10) | −0.0071 (12) | −0.0291 (11) |
C18 | 0.0508 (11) | 0.0454 (11) | 0.0598 (12) | 0.0002 (9) | −0.0112 (10) | −0.0207 (10) |
C19 | 0.0381 (9) | 0.0440 (10) | 0.0409 (10) | −0.0029 (8) | −0.0022 (8) | −0.0179 (8) |
C20 | 0.0403 (10) | 0.0430 (10) | 0.0429 (10) | 0.0032 (8) | −0.0078 (8) | −0.0186 (8) |
C21 | 0.0495 (12) | 0.0774 (16) | 0.0482 (12) | −0.0078 (11) | 0.0001 (10) | −0.0155 (11) |
C22 | 0.0387 (9) | 0.0408 (10) | 0.0440 (10) | 0.0033 (8) | −0.0092 (8) | −0.0180 (8) |
C23 | 0.0547 (12) | 0.0505 (12) | 0.0479 (11) | 0.0092 (9) | −0.0062 (9) | −0.0222 (9) |
C24 | 0.0543 (12) | 0.0568 (13) | 0.0685 (15) | 0.0189 (10) | −0.0093 (11) | −0.0262 (11) |
C25 | 0.0702 (15) | 0.0601 (14) | 0.0691 (15) | 0.0230 (12) | −0.0283 (12) | −0.0216 (12) |
C26 | 0.0904 (18) | 0.0718 (16) | 0.0495 (12) | 0.0267 (14) | −0.0269 (12) | −0.0255 (11) |
C27 | 0.0608 (13) | 0.0574 (13) | 0.0470 (11) | 0.0189 (10) | −0.0144 (10) | −0.0253 (10) |
O1 | 0.0419 (7) | 0.0418 (7) | 0.0486 (7) | 0.0073 (5) | −0.0137 (6) | −0.0227 (6) |
O2 | 0.0577 (8) | 0.0528 (8) | 0.0416 (7) | 0.0031 (6) | −0.0179 (6) | −0.0196 (6) |
O3 | 0.0823 (11) | 0.0510 (9) | 0.0523 (8) | 0.0109 (8) | −0.0321 (8) | −0.0152 (7) |
O4 | 0.0551 (9) | 0.0886 (12) | 0.0428 (8) | −0.0160 (8) | −0.0074 (7) | −0.0232 (8) |
O5 | 0.0427 (8) | 0.0716 (10) | 0.0443 (8) | −0.0093 (7) | −0.0066 (6) | −0.0136 (7) |
O6 | 0.0612 (9) | 0.0767 (11) | 0.0413 (8) | 0.0107 (8) | −0.0009 (7) | −0.0120 (8) |
C28 | 0.083 (4) | 0.064 (4) | 0.115 (5) | 0.022 (3) | −0.051 (4) | −0.021 (4) |
C29 | 0.110 (6) | 0.070 (4) | 0.150 (6) | 0.031 (3) | −0.082 (5) | −0.056 (4) |
C30 | 0.117 (8) | 0.110 (6) | 0.120 (6) | 0.042 (5) | −0.062 (5) | −0.046 (5) |
C31 | 0.107 (6) | 0.153 (10) | 0.191 (8) | 0.009 (8) | −0.089 (5) | −0.006 (7) |
C32 | 0.167 (14) | 0.176 (10) | 0.290 (19) | 0.025 (9) | −0.169 (14) | −0.046 (10) |
C33 | 0.086 (5) | 0.067 (4) | 0.085 (4) | −0.002 (3) | −0.029 (4) | −0.012 (3) |
C34 | 0.169 (10) | 0.139 (9) | 0.181 (10) | 0.062 (8) | −0.094 (8) | −0.074 (9) |
C281 | 0.125 (12) | 0.175 (16) | 0.174 (12) | 0.066 (11) | −0.084 (10) | −0.081 (12) |
C291 | 0.070 (6) | 0.091 (7) | 0.147 (10) | 0.019 (5) | −0.051 (6) | −0.038 (6) |
C301 | 0.086 (7) | 0.081 (6) | 0.180 (11) | 0.012 (5) | −0.029 (6) | −0.055 (7) |
C311 | 0.077 (6) | 0.069 (6) | 0.192 (10) | 0.016 (4) | −0.039 (6) | −0.048 (6) |
C321 | 0.066 (6) | 0.077 (6) | 0.157 (11) | 0.001 (4) | −0.023 (7) | −0.035 (6) |
C331 | 0.19 (2) | 0.062 (8) | 0.39 (4) | −0.033 (11) | −0.20 (3) | 0.011 (14) |
C341 | 0.116 (10) | 0.22 (2) | 0.119 (12) | −0.057 (13) | −0.038 (9) | 0.055 (14) |
Geometric parameters (Å, º) top
Br1—C8 | 1.897 (2) | C21—H21A | 0.9600 |
C1—O1 | 1.433 (2) | C21—H21B | 0.9600 |
C1—C5 | 1.506 (3) | C21—H21C | 0.9600 |
C1—C2 | 1.581 (3) | C22—C27 | 1.381 (3) |
C1—H1 | 0.9800 | C22—C23 | 1.385 (3) |
C2—C13 | 1.514 (3) | C23—C24 | 1.381 (3) |
C2—C3 | 1.531 (2) | C23—H23 | 0.9300 |
C2—C11 | 1.559 (3) | C24—C25 | 1.368 (4) |
C3—C19 | 1.501 (3) | C24—H24 | 0.9300 |
C3—C4 | 1.545 (3) | C25—C26 | 1.377 (4) |
C3—H3 | 0.9800 | C25—H25 | 0.9300 |
C4—O1 | 1.436 (2) | C26—C27 | 1.380 (3) |
C4—C22 | 1.516 (3) | C26—H26 | 0.9300 |
C4—C20 | 1.541 (3) | C27—H27 | 0.9300 |
C5—C6 | 1.380 (3) | C28—C34 | 1.386 (11) |
C5—C10 | 1.386 (3) | C28—C29 | 1.3900 |
C6—C7 | 1.384 (3) | C28—C33 | 1.3900 |
C6—H6 | 0.9300 | C29—C30 | 1.3900 |
C7—C8 | 1.379 (3) | C29—H29 | 0.9300 |
C7—H7 | 0.9300 | C30—C31 | 1.3900 |
C8—C9 | 1.369 (3) | C30—H30 | 0.9300 |
C9—C10 | 1.380 (3) | C31—C32 | 1.3900 |
C9—H9 | 0.9300 | C31—H31 | 0.9300 |
C10—H10 | 0.9300 | C32—C33 | 1.3900 |
C11—O6 | 1.195 (2) | C32—H32 | 0.9300 |
C11—C12 | 1.489 (3) | C33—H33 | 0.9300 |
C12—H12A | 0.9600 | C34—H34A | 0.9600 |
C12—H12B | 0.9600 | C34—H34B | 0.9600 |
C12—H12C | 0.9600 | C34—H34C | 0.9600 |
C13—O3 | 1.197 (2) | C281—C341 | 1.369 (13) |
C13—O2 | 1.351 (2) | C281—C291 | 1.3900 |
C14—C19 | 1.381 (3) | C281—C331 | 1.3900 |
C14—C15 | 1.388 (3) | C291—C301 | 1.3900 |
C14—O2 | 1.397 (2) | C291—H291 | 0.9300 |
C15—C16 | 1.368 (3) | C301—C311 | 1.3900 |
C15—H15 | 0.9300 | C301—H301 | 0.9300 |
C16—C17 | 1.379 (4) | C311—C321 | 1.3900 |
C16—H16 | 0.9300 | C311—H311 | 0.9300 |
C17—C18 | 1.385 (3) | C321—C331 | 1.3900 |
C17—H17 | 0.9300 | C321—H321 | 0.9300 |
C18—C19 | 1.390 (3) | C331—H331 | 0.9300 |
C18—H18 | 0.9300 | C341—H34D | 0.9600 |
C20—O4 | 1.196 (2) | C341—H34E | 0.9600 |
C20—O5 | 1.318 (2) | C341—H34F | 0.9600 |
C21—O5 | 1.452 (3) | | |
| | | |
O1—C1—C5 | 110.04 (15) | O5—C21—H21A | 109.5 |
O1—C1—C2 | 105.20 (14) | O5—C21—H21B | 109.5 |
C5—C1—C2 | 116.85 (15) | H21A—C21—H21B | 109.5 |
O1—C1—H1 | 108.1 | O5—C21—H21C | 109.5 |
C5—C1—H1 | 108.1 | H21A—C21—H21C | 109.5 |
C2—C1—H1 | 108.1 | H21B—C21—H21C | 109.5 |
C13—C2—C3 | 113.88 (15) | C27—C22—C23 | 118.52 (18) |
C13—C2—C11 | 109.69 (15) | C27—C22—C4 | 118.92 (17) |
C3—C2—C11 | 109.73 (15) | C23—C22—C4 | 122.43 (17) |
C13—C2—C1 | 109.30 (15) | C24—C23—C22 | 120.7 (2) |
C3—C2—C1 | 102.86 (14) | C24—C23—H23 | 119.6 |
C11—C2—C1 | 111.24 (15) | C22—C23—H23 | 119.6 |
C19—C3—C2 | 113.31 (15) | C25—C24—C23 | 120.4 (2) |
C19—C3—C4 | 120.42 (15) | C25—C24—H24 | 119.8 |
C2—C3—C4 | 104.29 (14) | C23—C24—H24 | 119.8 |
C19—C3—H3 | 105.9 | C24—C25—C26 | 119.4 (2) |
C2—C3—H3 | 105.9 | C24—C25—H25 | 120.3 |
C4—C3—H3 | 105.9 | C26—C25—H25 | 120.3 |
O1—C4—C22 | 109.02 (14) | C25—C26—C27 | 120.6 (2) |
O1—C4—C20 | 106.93 (14) | C25—C26—H26 | 119.7 |
C22—C4—C20 | 113.83 (15) | C27—C26—H26 | 119.7 |
O1—C4—C3 | 101.45 (14) | C26—C27—C22 | 120.4 (2) |
C22—C4—C3 | 112.32 (15) | C26—C27—H27 | 119.8 |
C20—C4—C3 | 112.35 (15) | C22—C27—H27 | 119.8 |
C6—C5—C10 | 118.85 (18) | C1—O1—C4 | 107.49 (13) |
C6—C5—C1 | 122.54 (17) | C13—O2—C14 | 121.57 (15) |
C10—C5—C1 | 118.58 (17) | C20—O5—C21 | 116.85 (16) |
C5—C6—C7 | 120.66 (19) | C34—C28—C29 | 123.5 (7) |
C5—C6—H6 | 119.7 | C34—C28—C33 | 116.4 (7) |
C7—C6—H6 | 119.7 | C29—C28—C33 | 120.0 |
C8—C7—C6 | 119.1 (2) | C30—C29—C28 | 120.0 |
C8—C7—H7 | 120.5 | C30—C29—H29 | 120.0 |
C6—C7—H7 | 120.5 | C28—C29—H29 | 120.0 |
C9—C8—C7 | 121.3 (2) | C31—C30—C29 | 120.0 |
C9—C8—Br1 | 118.82 (16) | C31—C30—H30 | 120.0 |
C7—C8—Br1 | 119.81 (17) | C29—C30—H30 | 120.0 |
C8—C9—C10 | 118.93 (19) | C30—C31—C32 | 120.0 |
C8—C9—H9 | 120.5 | C30—C31—H31 | 120.0 |
C10—C9—H9 | 120.5 | C32—C31—H31 | 120.0 |
C9—C10—C5 | 121.09 (19) | C33—C32—C31 | 120.0 |
C9—C10—H10 | 119.5 | C33—C32—H32 | 120.0 |
C5—C10—H10 | 119.5 | C31—C32—H32 | 120.0 |
O6—C11—C12 | 122.38 (19) | C32—C33—C28 | 120.0 |
O6—C11—C2 | 118.59 (17) | C32—C33—H33 | 120.0 |
C12—C11—C2 | 119.01 (17) | C28—C33—H33 | 120.0 |
C11—C12—H12A | 109.5 | C28—C34—H34A | 109.5 |
C11—C12—H12B | 109.5 | C28—C34—H34B | 109.5 |
H12A—C12—H12B | 109.5 | H34A—C34—H34B | 109.5 |
C11—C12—H12C | 109.5 | C28—C34—H34C | 109.5 |
H12A—C12—H12C | 109.5 | H34A—C34—H34C | 109.5 |
H12B—C12—H12C | 109.5 | H34B—C34—H34C | 109.5 |
O3—C13—O2 | 117.93 (17) | C341—C281—C291 | 121.8 (15) |
O3—C13—C2 | 123.78 (18) | C341—C281—C331 | 118.1 (15) |
O2—C13—C2 | 118.08 (17) | C291—C281—C331 | 120.0 |
C19—C14—C15 | 122.5 (2) | C301—C291—C281 | 120.0 |
C19—C14—O2 | 122.39 (17) | C301—C291—H291 | 120.0 |
C15—C14—O2 | 115.08 (18) | C281—C291—H291 | 120.0 |
C16—C15—C14 | 118.8 (2) | C311—C301—C291 | 120.0 |
C16—C15—H15 | 120.6 | C311—C301—H301 | 120.0 |
C14—C15—H15 | 120.6 | C291—C301—H301 | 120.0 |
C15—C16—C17 | 120.5 (2) | C301—C311—C321 | 120.0 |
C15—C16—H16 | 119.7 | C301—C311—H311 | 120.0 |
C17—C16—H16 | 119.7 | C321—C311—H311 | 120.0 |
C16—C17—C18 | 119.9 (2) | C311—C321—C331 | 120.0 |
C16—C17—H17 | 120.0 | C311—C321—H321 | 120.0 |
C18—C17—H17 | 120.0 | C331—C321—H321 | 120.0 |
C17—C18—C19 | 121.0 (2) | C321—C331—C281 | 120.0 |
C17—C18—H18 | 119.5 | C321—C331—H331 | 120.0 |
C19—C18—H18 | 119.5 | C281—C331—H331 | 120.0 |
C14—C19—C18 | 117.22 (18) | C281—C341—H34D | 109.5 |
C14—C19—C3 | 120.54 (17) | C281—C341—H34E | 109.5 |
C18—C19—C3 | 122.13 (18) | H34D—C341—H34E | 109.5 |
O4—C20—O5 | 124.19 (18) | C281—C341—H34F | 109.5 |
O4—C20—C4 | 123.75 (17) | H34D—C341—H34F | 109.5 |
O5—C20—C4 | 111.90 (16) | H34E—C341—H34F | 109.5 |
| | | |
O1—C1—C2—C13 | 129.03 (15) | C17—C18—C19—C14 | −1.2 (3) |
C5—C1—C2—C13 | −108.59 (18) | C17—C18—C19—C3 | −177.60 (19) |
O1—C1—C2—C3 | 7.70 (17) | C2—C3—C19—C14 | −13.5 (2) |
C5—C1—C2—C3 | 130.08 (16) | C4—C3—C19—C14 | 110.9 (2) |
O1—C1—C2—C11 | −109.71 (16) | C2—C3—C19—C18 | 162.74 (17) |
C5—C1—C2—C11 | 12.7 (2) | C4—C3—C19—C18 | −72.9 (2) |
C13—C2—C3—C19 | 32.5 (2) | O1—C4—C20—O4 | 106.9 (2) |
C11—C2—C3—C19 | −90.91 (18) | C22—C4—C20—O4 | −132.7 (2) |
C1—C2—C3—C19 | 150.62 (15) | C3—C4—C20—O4 | −3.6 (3) |
C13—C2—C3—C4 | −100.26 (17) | O1—C4—C20—O5 | −68.77 (19) |
C11—C2—C3—C4 | 136.36 (15) | C22—C4—C20—O5 | 51.7 (2) |
C1—C2—C3—C4 | 17.89 (17) | C3—C4—C20—O5 | −179.23 (16) |
C19—C3—C4—O1 | −166.01 (15) | O1—C4—C22—C27 | −40.6 (2) |
C2—C3—C4—O1 | −37.48 (16) | C20—C4—C22—C27 | −159.83 (18) |
C19—C3—C4—C22 | 77.7 (2) | C3—C4—C22—C27 | 71.1 (2) |
C2—C3—C4—C22 | −153.75 (15) | O1—C4—C22—C23 | 143.51 (18) |
C19—C3—C4—C20 | −52.1 (2) | C20—C4—C22—C23 | 24.2 (3) |
C2—C3—C4—C20 | 76.38 (18) | C3—C4—C22—C23 | −104.9 (2) |
O1—C1—C5—C6 | 25.2 (2) | C27—C22—C23—C24 | 1.3 (3) |
C2—C1—C5—C6 | −94.6 (2) | C4—C22—C23—C24 | 177.29 (19) |
O1—C1—C5—C10 | −157.04 (17) | C22—C23—C24—C25 | −0.2 (4) |
C2—C1—C5—C10 | 83.1 (2) | C23—C24—C25—C26 | −1.1 (4) |
C10—C5—C6—C7 | −0.4 (3) | C24—C25—C26—C27 | 1.2 (4) |
C1—C5—C6—C7 | 177.35 (19) | C25—C26—C27—C22 | −0.1 (4) |
C5—C6—C7—C8 | −1.5 (3) | C23—C22—C27—C26 | −1.2 (3) |
C6—C7—C8—C9 | 2.1 (3) | C4—C22—C27—C26 | −177.3 (2) |
C6—C7—C8—Br1 | −176.33 (17) | C5—C1—O1—C4 | −159.79 (14) |
C7—C8—C9—C10 | −0.7 (3) | C2—C1—O1—C4 | −33.12 (17) |
Br1—C8—C9—C10 | 177.69 (17) | C22—C4—O1—C1 | 162.98 (14) |
C8—C9—C10—C5 | −1.2 (3) | C20—C4—O1—C1 | −73.55 (17) |
C6—C5—C10—C9 | 1.8 (3) | C3—C4—O1—C1 | 44.31 (17) |
C1—C5—C10—C9 | −176.06 (19) | O3—C13—O2—C14 | −165.03 (18) |
C13—C2—C11—O6 | −158.73 (19) | C2—C13—O2—C14 | 20.0 (3) |
C3—C2—C11—O6 | −32.9 (2) | C19—C14—O2—C13 | 1.6 (3) |
C1—C2—C11—O6 | 80.2 (2) | C15—C14—O2—C13 | −179.97 (17) |
C13—C2—C11—C12 | 22.5 (2) | O4—C20—O5—C21 | 2.8 (3) |
C3—C2—C11—C12 | 148.35 (18) | C4—C20—O5—C21 | 178.43 (18) |
C1—C2—C11—C12 | −98.5 (2) | C34—C28—C29—C30 | −178.0 (8) |
C3—C2—C13—O3 | 148.3 (2) | C33—C28—C29—C30 | 0.0 |
C11—C2—C13—O3 | −88.3 (2) | C28—C29—C30—C31 | 0.0 |
C1—C2—C13—O3 | 33.9 (3) | C29—C30—C31—C32 | 0.0 |
C3—C2—C13—O2 | −37.0 (2) | C30—C31—C32—C33 | 0.0 |
C11—C2—C13—O2 | 86.4 (2) | C31—C32—C33—C28 | 0.0 |
C1—C2—C13—O2 | −151.37 (16) | C34—C28—C33—C32 | 178.2 (7) |
C19—C14—C15—C16 | 0.1 (3) | C29—C28—C33—C32 | 0.0 |
O2—C14—C15—C16 | −178.30 (18) | C341—C281—C291—C301 | 177.5 (14) |
C14—C15—C16—C17 | −0.6 (3) | C331—C281—C291—C301 | 0.0 |
C15—C16—C17—C18 | 0.1 (3) | C281—C291—C301—C311 | 0.0 |
C16—C17—C18—C19 | 0.8 (3) | C291—C301—C311—C321 | 0.0 |
C15—C14—C19—C18 | 0.8 (3) | C301—C311—C321—C331 | 0.0 |
O2—C14—C19—C18 | 179.09 (17) | C311—C321—C331—C281 | 0.0 |
C15—C14—C19—C3 | 177.21 (17) | C341—C281—C331—C321 | −177.6 (13) |
O2—C14—C19—C3 | −4.5 (3) | C291—C281—C331—C321 | 0.0 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O3 | 0.98 | 2.44 | 2.837 (2) | 104 |
C3—H3···O6 | 0.98 | 2.23 | 2.766 (2) | 113 |
C6—H6···O6i | 0.93 | 2.52 | 3.289 (3) | 140 |
C12—H12A···O5ii | 0.96 | 2.58 | 3.478 (3) | 155 |
C21—H21A···O4iii | 0.96 | 2.63 | 3.585 (3) | 176 |
C25—H25···Br1iv | 0.93 | 3.13 | 3.840 (2) | 134 |
C24—H24···Cg1v | 0.93 | 3.02 | 3.689 (2) | 123 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) x+1, y, z; (iii) −x, −y+2, −z+1; (iv) x−1, y+1, z; (v) x−1, y, z. |
(Ic) Methyl 3a-acetyl-3-(4-bromophenyl)-4-oxo-1-phenyl-3,3a,4,9b-tetrahydro-1
H-furo[3,4-
c]chromene-1-carboxylate xylene monosolvate
top
Crystal data top
C27H21BrO6·C8H10 | Z = 2 |
Mr = 627.51 | F(000) = 648 |
Triclinic, P1 | Dx = 1.417 Mg m−3 |
a = 8.2587 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.7841 (9) Å | Cell parameters from 4020 reflections |
c = 15.6238 (11) Å | θ = 2.5–23.1° |
α = 66.446 (1)° | µ = 1.44 mm−1 |
β = 76.634 (1)° | T = 294 K |
γ = 86.030 (1)° | Block, colourless |
V = 1470.67 (18) Å3 | 0.18 × 0.16 × 0.01 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3867 reflections with I > 2σ(I) |
ω scans | Rint = 0.025 |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | θmax = 25.0°, θmin = 1.7° |
Tmin = 0.82, Tmax = 0.96 | h = −9→9 |
14351 measured reflections | k = −15→15 |
5185 independent reflections | l = −18→18 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0574P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.14 | (Δ/σ)max = 0.001 |
5185 reflections | Δρmax = 0.55 e Å−3 |
383 parameters | Δρmin = −0.35 e Å−3 |
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 | |
Br1 | 1.18906 (4) | 0.04688 (3) | 0.53253 (3) | 0.08678 (17) | |
C1 | 0.8692 (3) | 0.33702 (18) | 0.75785 (16) | 0.0399 (5) | |
H1 | 0.8290 | 0.2853 | 0.8249 | 0.048* | |
C2 | 0.9911 (3) | 0.42971 (18) | 0.75456 (15) | 0.0389 (5) | |
C3 | 0.8873 (3) | 0.53764 (18) | 0.73159 (15) | 0.0380 (5) | |
H3 | 0.9188 | 0.5794 | 0.6620 | 0.046* | |
C4 | 0.7064 (3) | 0.49283 (18) | 0.75389 (15) | 0.0379 (5) | |
C5 | 0.9391 (3) | 0.26627 (18) | 0.70137 (15) | 0.0400 (5) | |
C6 | 0.9211 (3) | 0.2930 (2) | 0.60977 (17) | 0.0503 (6) | |
H6 | 0.8601 | 0.3561 | 0.5811 | 0.060* | |
C7 | 0.9928 (3) | 0.2270 (2) | 0.55958 (18) | 0.0552 (7) | |
H7 | 0.9795 | 0.2455 | 0.4977 | 0.066* | |
C8 | 1.0835 (3) | 0.1344 (2) | 0.60187 (19) | 0.0514 (6) | |
C9 | 1.1017 (3) | 0.1051 (2) | 0.6937 (2) | 0.0550 (7) | |
H9 | 1.1626 | 0.0418 | 0.7221 | 0.066* | |
C10 | 1.0291 (3) | 0.17039 (19) | 0.74341 (17) | 0.0476 (6) | |
H10 | 1.0401 | 0.1503 | 0.8059 | 0.057* | |
C11 | 1.1499 (3) | 0.4488 (2) | 0.67254 (17) | 0.0422 (5) | |
C12 | 1.3041 (3) | 0.3881 (2) | 0.69551 (19) | 0.0560 (7) | |
H12A | 1.3895 | 0.4073 | 0.6379 | 0.084* | |
H12B | 1.2820 | 0.3072 | 0.7236 | 0.084* | |
H12C | 1.3407 | 0.4104 | 0.7399 | 0.084* | |
C13 | 1.0381 (3) | 0.3899 (2) | 0.85044 (16) | 0.0448 (6) | |
C14 | 1.0175 (3) | 0.5811 (2) | 0.84376 (16) | 0.0433 (6) | |
C15 | 1.0590 (3) | 0.6521 (2) | 0.88319 (17) | 0.0519 (6) | |
H15 | 1.1206 | 0.6252 | 0.9302 | 0.062* | |
C16 | 1.0079 (3) | 0.7631 (2) | 0.8520 (2) | 0.0600 (7) | |
H16 | 1.0335 | 0.8116 | 0.8785 | 0.072* | |
C17 | 0.9187 (3) | 0.8024 (2) | 0.7813 (2) | 0.0610 (7) | |
H17 | 0.8849 | 0.8777 | 0.7598 | 0.073* | |
C18 | 0.8792 (3) | 0.7306 (2) | 0.74233 (19) | 0.0531 (6) | |
H18 | 0.8203 | 0.7586 | 0.6940 | 0.064* | |
C19 | 0.9257 (3) | 0.6171 (2) | 0.77392 (16) | 0.0411 (5) | |
C20 | 0.6297 (3) | 0.44175 (19) | 0.86234 (16) | 0.0407 (5) | |
C21 | 0.3933 (3) | 0.3492 (2) | 0.98211 (17) | 0.0578 (7) | |
H21A | 0.4538 | 0.2834 | 1.0132 | 0.087* | |
H21B | 0.2819 | 0.3262 | 0.9874 | 0.087* | |
H21C | 0.3895 | 0.4022 | 1.0121 | 0.087* | |
C22 | 0.5985 (3) | 0.57999 (18) | 0.69493 (15) | 0.0393 (5) | |
C23 | 0.4810 (3) | 0.6416 (2) | 0.73360 (18) | 0.0500 (6) | |
H23 | 0.4646 | 0.6282 | 0.7981 | 0.060* | |
C24 | 0.3883 (3) | 0.7224 (2) | 0.67726 (19) | 0.0586 (7) | |
H24 | 0.3104 | 0.7635 | 0.7038 | 0.070* | |
C25 | 0.4109 (4) | 0.7423 (2) | 0.5823 (2) | 0.0644 (8) | |
H25 | 0.3465 | 0.7953 | 0.5446 | 0.077* | |
C26 | 0.5292 (4) | 0.6834 (2) | 0.54312 (19) | 0.0640 (8) | |
H26 | 0.5463 | 0.6980 | 0.4784 | 0.077* | |
C27 | 0.6226 (3) | 0.6030 (2) | 0.59879 (17) | 0.0512 (6) | |
H27 | 0.7026 | 0.5639 | 0.5713 | 0.061* | |
O1 | 0.73120 (18) | 0.39987 (12) | 0.72332 (10) | 0.0413 (4) | |
O2 | 1.0710 (2) | 0.46945 (14) | 0.88110 (11) | 0.0490 (4) | |
O3 | 1.0585 (2) | 0.29193 (15) | 0.89781 (12) | 0.0604 (5) | |
O4 | 0.7052 (2) | 0.42978 (17) | 0.92187 (12) | 0.0641 (5) | |
O5 | 0.47558 (19) | 0.40353 (15) | 0.88184 (11) | 0.0528 (4) | |
O6 | 1.1413 (2) | 0.51006 (17) | 0.59264 (12) | 0.0654 (5) | |
C28 | 0.5034 (3) | 0.0100 (2) | 0.76479 (19) | 0.0600 (7) | |
C29 | 0.4088 (4) | −0.0818 (3) | 0.8361 (2) | 0.0696 (8) | |
H29 | 0.4046 | −0.1494 | 0.8276 | 0.083* | |
C30 | 0.3205 (4) | −0.0743 (3) | 0.9200 (2) | 0.0688 (8) | |
H30 | 0.2567 | −0.1371 | 0.9665 | 0.083* | |
C31 | 0.3241 (3) | 0.0232 (2) | 0.93670 (19) | 0.0598 (7) | |
C32 | 0.4196 (4) | 0.1132 (2) | 0.8664 (2) | 0.0664 (8) | |
H32 | 0.4253 | 0.1803 | 0.8755 | 0.080* | |
C33 | 0.5079 (4) | 0.1067 (2) | 0.7821 (2) | 0.0645 (8) | |
H33 | 0.5721 | 0.1694 | 0.7359 | 0.077* | |
C34 | 0.5929 (4) | 0.0038 (3) | 0.6713 (2) | 0.0899 (10) | |
H34A | 0.5325 | 0.0450 | 0.6228 | 0.135* | |
H34B | 0.6006 | −0.0745 | 0.6788 | 0.135* | |
H34C | 0.7028 | 0.0370 | 0.6528 | 0.135* | |
C35 | 0.2265 (4) | 0.0314 (3) | 1.0282 (2) | 0.0916 (11) | |
H35A | 0.1162 | 0.0000 | 1.0435 | 0.137* | |
H35B | 0.2201 | 0.1100 | 1.0200 | 0.137* | |
H35C | 0.2812 | −0.0106 | 1.0794 | 0.137* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0940 (3) | 0.0840 (3) | 0.0987 (3) | 0.01728 (19) | −0.0094 (2) | −0.0619 (2) |
C1 | 0.0397 (13) | 0.0417 (13) | 0.0351 (12) | 0.0015 (10) | −0.0085 (10) | −0.0118 (10) |
C2 | 0.0378 (12) | 0.0451 (13) | 0.0331 (12) | 0.0035 (10) | −0.0088 (10) | −0.0146 (10) |
C3 | 0.0374 (12) | 0.0408 (12) | 0.0321 (11) | 0.0015 (10) | −0.0068 (10) | −0.0112 (10) |
C4 | 0.0372 (12) | 0.0421 (13) | 0.0362 (12) | 0.0006 (10) | −0.0074 (10) | −0.0176 (10) |
C5 | 0.0395 (13) | 0.0380 (12) | 0.0399 (13) | −0.0020 (10) | −0.0080 (10) | −0.0127 (10) |
C6 | 0.0572 (16) | 0.0465 (14) | 0.0450 (14) | 0.0092 (12) | −0.0153 (12) | −0.0149 (12) |
C7 | 0.0641 (17) | 0.0591 (16) | 0.0430 (14) | 0.0007 (14) | −0.0075 (12) | −0.0229 (13) |
C8 | 0.0470 (14) | 0.0494 (15) | 0.0589 (16) | 0.0023 (12) | −0.0037 (12) | −0.0270 (13) |
C9 | 0.0535 (16) | 0.0442 (14) | 0.0688 (18) | 0.0086 (12) | −0.0166 (13) | −0.0232 (13) |
C10 | 0.0540 (15) | 0.0433 (14) | 0.0429 (13) | 0.0017 (12) | −0.0161 (12) | −0.0114 (11) |
C11 | 0.0416 (14) | 0.0471 (14) | 0.0398 (14) | −0.0020 (11) | −0.0074 (11) | −0.0194 (12) |
C12 | 0.0393 (14) | 0.0648 (17) | 0.0630 (16) | 0.0045 (12) | −0.0087 (12) | −0.0264 (14) |
C13 | 0.0428 (14) | 0.0540 (16) | 0.0379 (13) | 0.0043 (11) | −0.0110 (11) | −0.0178 (12) |
C14 | 0.0366 (12) | 0.0524 (15) | 0.0395 (13) | −0.0030 (11) | −0.0027 (10) | −0.0193 (11) |
C15 | 0.0434 (14) | 0.0711 (18) | 0.0449 (14) | −0.0088 (13) | −0.0033 (11) | −0.0285 (13) |
C16 | 0.0531 (16) | 0.0705 (19) | 0.0676 (18) | −0.0091 (14) | −0.0039 (14) | −0.0423 (15) |
C17 | 0.0604 (17) | 0.0513 (16) | 0.0775 (19) | 0.0011 (13) | −0.0135 (15) | −0.0329 (15) |
C18 | 0.0490 (15) | 0.0504 (15) | 0.0616 (16) | 0.0005 (12) | −0.0155 (12) | −0.0220 (13) |
C19 | 0.0355 (12) | 0.0472 (14) | 0.0391 (12) | −0.0032 (10) | −0.0040 (10) | −0.0171 (11) |
C20 | 0.0377 (13) | 0.0453 (13) | 0.0412 (13) | 0.0025 (10) | −0.0088 (11) | −0.0194 (11) |
C21 | 0.0472 (15) | 0.0697 (18) | 0.0418 (14) | −0.0068 (13) | 0.0009 (12) | −0.0117 (13) |
C22 | 0.0358 (12) | 0.0418 (13) | 0.0403 (13) | −0.0016 (10) | −0.0091 (10) | −0.0155 (10) |
C23 | 0.0496 (15) | 0.0527 (15) | 0.0443 (14) | 0.0070 (12) | −0.0071 (11) | −0.0182 (12) |
C24 | 0.0499 (15) | 0.0545 (16) | 0.0604 (17) | 0.0119 (13) | −0.0051 (13) | −0.0171 (14) |
C25 | 0.0599 (18) | 0.0586 (17) | 0.0645 (19) | 0.0155 (14) | −0.0222 (15) | −0.0116 (14) |
C26 | 0.078 (2) | 0.0679 (18) | 0.0436 (15) | 0.0134 (16) | −0.0225 (14) | −0.0161 (14) |
C27 | 0.0542 (15) | 0.0537 (15) | 0.0435 (14) | 0.0059 (12) | −0.0101 (12) | −0.0180 (12) |
O1 | 0.0375 (8) | 0.0448 (9) | 0.0449 (9) | 0.0048 (7) | −0.0126 (7) | −0.0197 (7) |
O2 | 0.0509 (10) | 0.0578 (11) | 0.0424 (9) | 0.0043 (8) | −0.0170 (8) | −0.0208 (8) |
O3 | 0.0800 (13) | 0.0536 (11) | 0.0486 (10) | 0.0135 (10) | −0.0324 (10) | −0.0132 (9) |
O4 | 0.0520 (11) | 0.0981 (15) | 0.0407 (10) | −0.0174 (10) | −0.0081 (9) | −0.0240 (10) |
O5 | 0.0387 (9) | 0.0698 (11) | 0.0414 (9) | −0.0078 (8) | −0.0072 (7) | −0.0126 (8) |
O6 | 0.0572 (11) | 0.0820 (13) | 0.0399 (10) | 0.0084 (10) | −0.0027 (8) | −0.0121 (10) |
C28 | 0.0563 (17) | 0.0654 (19) | 0.0576 (17) | 0.0163 (14) | −0.0223 (14) | −0.0208 (15) |
C29 | 0.086 (2) | 0.0555 (17) | 0.074 (2) | 0.0036 (16) | −0.0292 (18) | −0.0263 (16) |
C30 | 0.0672 (19) | 0.0603 (18) | 0.0648 (19) | −0.0095 (15) | −0.0181 (16) | −0.0067 (15) |
C31 | 0.0571 (17) | 0.0624 (18) | 0.0564 (17) | 0.0122 (14) | −0.0182 (14) | −0.0187 (15) |
C32 | 0.077 (2) | 0.0544 (17) | 0.070 (2) | 0.0091 (15) | −0.0203 (17) | −0.0258 (15) |
C33 | 0.0623 (18) | 0.0573 (18) | 0.0628 (18) | 0.0003 (14) | −0.0153 (15) | −0.0113 (15) |
C34 | 0.089 (2) | 0.110 (3) | 0.069 (2) | 0.024 (2) | −0.0163 (18) | −0.0382 (19) |
C35 | 0.088 (2) | 0.109 (3) | 0.066 (2) | 0.019 (2) | −0.0071 (18) | −0.031 (2) |
Geometric parameters (Å, º) top
Br1—C8 | 1.893 (2) | C17—H17 | 0.9300 |
C1—O1 | 1.431 (3) | C18—C19 | 1.392 (3) |
C1—C5 | 1.503 (3) | C18—H18 | 0.9300 |
C1—C2 | 1.585 (3) | C20—O4 | 1.191 (3) |
C1—H1 | 0.9800 | C20—O5 | 1.319 (3) |
C2—C13 | 1.512 (3) | C21—O5 | 1.450 (3) |
C2—C3 | 1.533 (3) | C21—H21A | 0.9600 |
C2—C11 | 1.562 (3) | C21—H21B | 0.9600 |
C3—C19 | 1.499 (3) | C21—H21C | 0.9600 |
C3—C4 | 1.549 (3) | C22—C27 | 1.378 (3) |
C3—H3 | 0.9800 | C22—C23 | 1.389 (3) |
C4—O1 | 1.434 (3) | C23—C24 | 1.380 (3) |
C4—C22 | 1.519 (3) | C23—H23 | 0.9300 |
C4—C20 | 1.541 (3) | C24—C25 | 1.370 (4) |
C5—C6 | 1.374 (3) | C24—H24 | 0.9300 |
C5—C10 | 1.394 (3) | C25—C26 | 1.373 (4) |
C6—C7 | 1.386 (3) | C25—H25 | 0.9300 |
C6—H6 | 0.9300 | C26—C27 | 1.376 (3) |
C7—C8 | 1.371 (4) | C26—H26 | 0.9300 |
C7—H7 | 0.9300 | C27—H27 | 0.9300 |
C8—C9 | 1.373 (4) | C28—C33 | 1.371 (4) |
C9—C10 | 1.375 (3) | C28—C29 | 1.381 (4) |
C9—H9 | 0.9300 | C28—C34 | 1.507 (4) |
C10—H10 | 0.9300 | C29—C30 | 1.380 (4) |
C11—O6 | 1.195 (3) | C29—H29 | 0.9300 |
C11—C12 | 1.485 (3) | C30—C31 | 1.376 (4) |
C12—H12A | 0.9600 | C30—H30 | 0.9300 |
C12—H12B | 0.9600 | C31—C32 | 1.366 (4) |
C12—H12C | 0.9600 | C31—C35 | 1.510 (4) |
C13—O3 | 1.197 (3) | C32—C33 | 1.382 (4) |
C13—O2 | 1.351 (3) | C32—H32 | 0.9300 |
C14—C19 | 1.382 (3) | C33—H33 | 0.9300 |
C14—C15 | 1.382 (3) | C34—H34A | 0.9600 |
C14—O2 | 1.393 (3) | C34—H34B | 0.9600 |
C15—C16 | 1.374 (4) | C34—H34C | 0.9600 |
C15—H15 | 0.9300 | C35—H35A | 0.9600 |
C16—C17 | 1.377 (4) | C35—H35B | 0.9600 |
C16—H16 | 0.9300 | C35—H35C | 0.9600 |
C17—C18 | 1.378 (4) | | |
| | | |
O1—C1—C5 | 109.91 (17) | C17—C18—C19 | 121.3 (2) |
O1—C1—C2 | 105.05 (16) | C17—C18—H18 | 119.4 |
C5—C1—C2 | 116.77 (18) | C19—C18—H18 | 119.4 |
O1—C1—H1 | 108.3 | C14—C19—C18 | 116.9 (2) |
C5—C1—H1 | 108.3 | C14—C19—C3 | 120.6 (2) |
C2—C1—H1 | 108.3 | C18—C19—C3 | 122.4 (2) |
C13—C2—C3 | 113.81 (18) | O4—C20—O5 | 123.8 (2) |
C13—C2—C11 | 110.52 (18) | O4—C20—C4 | 123.8 (2) |
C3—C2—C11 | 109.85 (17) | O5—C20—C4 | 112.20 (19) |
C13—C2—C1 | 108.75 (18) | O5—C21—H21A | 109.5 |
C3—C2—C1 | 102.97 (17) | O5—C21—H21B | 109.5 |
C11—C2—C1 | 110.69 (17) | H21A—C21—H21B | 109.5 |
C19—C3—C2 | 113.69 (18) | O5—C21—H21C | 109.5 |
C19—C3—C4 | 119.85 (18) | H21A—C21—H21C | 109.5 |
C2—C3—C4 | 104.27 (17) | H21B—C21—H21C | 109.5 |
C19—C3—H3 | 106.0 | C27—C22—C23 | 118.5 (2) |
C2—C3—H3 | 106.0 | C27—C22—C4 | 119.2 (2) |
C4—C3—H3 | 106.0 | C23—C22—C4 | 122.2 (2) |
O1—C4—C22 | 108.68 (16) | C24—C23—C22 | 120.6 (2) |
O1—C4—C20 | 107.09 (16) | C24—C23—H23 | 119.7 |
C22—C4—C20 | 113.98 (18) | C22—C23—H23 | 119.7 |
O1—C4—C3 | 101.66 (16) | C25—C24—C23 | 120.1 (3) |
C22—C4—C3 | 112.61 (17) | C25—C24—H24 | 120.0 |
C20—C4—C3 | 111.87 (18) | C23—C24—H24 | 120.0 |
C6—C5—C10 | 118.6 (2) | C24—C25—C26 | 119.6 (2) |
C6—C5—C1 | 123.1 (2) | C24—C25—H25 | 120.2 |
C10—C5—C1 | 118.3 (2) | C26—C25—H25 | 120.2 |
C5—C6—C7 | 120.8 (2) | C25—C26—C27 | 120.6 (2) |
C5—C6—H6 | 119.6 | C25—C26—H26 | 119.7 |
C7—C6—H6 | 119.6 | C27—C26—H26 | 119.7 |
C8—C7—C6 | 119.4 (2) | C26—C27—C22 | 120.5 (2) |
C8—C7—H7 | 120.3 | C26—C27—H27 | 119.7 |
C6—C7—H7 | 120.3 | C22—C27—H27 | 119.7 |
C7—C8—C9 | 120.9 (2) | C1—O1—C4 | 107.63 (15) |
C7—C8—Br1 | 119.9 (2) | C13—O2—C14 | 122.04 (18) |
C9—C8—Br1 | 119.17 (19) | C20—O5—C21 | 116.96 (19) |
C8—C9—C10 | 119.4 (2) | C33—C28—C29 | 117.1 (3) |
C8—C9—H9 | 120.3 | C33—C28—C34 | 122.1 (3) |
C10—C9—H9 | 120.3 | C29—C28—C34 | 120.8 (3) |
C9—C10—C5 | 120.9 (2) | C30—C29—C28 | 120.8 (3) |
C9—C10—H10 | 119.6 | C30—C29—H29 | 119.6 |
C5—C10—H10 | 119.6 | C28—C29—H29 | 119.6 |
O6—C11—C12 | 122.2 (2) | C31—C30—C29 | 121.9 (3) |
O6—C11—C2 | 118.4 (2) | C31—C30—H30 | 119.0 |
C12—C11—C2 | 119.3 (2) | C29—C30—H30 | 119.0 |
C11—C12—H12A | 109.5 | C32—C31—C30 | 117.0 (3) |
C11—C12—H12B | 109.5 | C32—C31—C35 | 121.2 (3) |
H12A—C12—H12B | 109.5 | C30—C31—C35 | 121.8 (3) |
C11—C12—H12C | 109.5 | C31—C32—C33 | 121.5 (3) |
H12A—C12—H12C | 109.5 | C31—C32—H32 | 119.2 |
H12B—C12—H12C | 109.5 | C33—C32—H32 | 119.2 |
O3—C13—O2 | 118.0 (2) | C28—C33—C32 | 121.7 (3) |
O3—C13—C2 | 123.4 (2) | C28—C33—H33 | 119.2 |
O2—C13—C2 | 118.4 (2) | C32—C33—H33 | 119.2 |
C19—C14—C15 | 122.6 (2) | C28—C34—H34A | 109.5 |
C19—C14—O2 | 122.1 (2) | C28—C34—H34B | 109.5 |
C15—C14—O2 | 115.3 (2) | H34A—C34—H34B | 109.5 |
C16—C15—C14 | 119.1 (2) | C28—C34—H34C | 109.5 |
C16—C15—H15 | 120.4 | H34A—C34—H34C | 109.5 |
C14—C15—H15 | 120.4 | H34B—C34—H34C | 109.5 |
C15—C16—C17 | 119.9 (2) | C31—C35—H35A | 109.5 |
C15—C16—H16 | 120.1 | C31—C35—H35B | 109.5 |
C17—C16—H16 | 120.1 | H35A—C35—H35B | 109.5 |
C16—C17—C18 | 120.3 (3) | C31—C35—H35C | 109.5 |
C16—C17—H17 | 119.9 | H35A—C35—H35C | 109.5 |
C18—C17—H17 | 119.9 | H35B—C35—H35C | 109.5 |
| | | |
O1—C1—C2—C13 | 129.95 (18) | O2—C14—C19—C18 | 179.9 (2) |
C5—C1—C2—C13 | −108.0 (2) | C15—C14—C19—C3 | 178.5 (2) |
O1—C1—C2—C3 | 8.9 (2) | O2—C14—C19—C3 | −3.2 (3) |
C5—C1—C2—C3 | 130.94 (19) | C17—C18—C19—C14 | −2.0 (4) |
O1—C1—C2—C11 | −108.46 (19) | C17—C18—C19—C3 | −178.8 (2) |
C5—C1—C2—C11 | 13.6 (3) | C2—C3—C19—C14 | −13.8 (3) |
C13—C2—C3—C19 | 31.3 (3) | C4—C3—C19—C14 | 110.4 (2) |
C11—C2—C3—C19 | −93.3 (2) | C2—C3—C19—C18 | 163.0 (2) |
C1—C2—C3—C19 | 148.80 (17) | C4—C3—C19—C18 | −72.8 (3) |
C13—C2—C3—C4 | −101.0 (2) | O1—C4—C20—O4 | 104.8 (3) |
C11—C2—C3—C4 | 134.49 (18) | C22—C4—C20—O4 | −135.0 (2) |
C1—C2—C3—C4 | 16.5 (2) | C3—C4—C20—O4 | −5.8 (3) |
C19—C3—C4—O1 | −165.07 (17) | O1—C4—C20—O5 | −69.5 (2) |
C2—C3—C4—O1 | −36.46 (19) | C22—C4—C20—O5 | 50.7 (3) |
C19—C3—C4—C22 | 78.8 (2) | C3—C4—C20—O5 | 179.93 (18) |
C2—C3—C4—C22 | −152.58 (17) | O1—C4—C22—C27 | −39.0 (3) |
C19—C3—C4—C20 | −51.1 (3) | C20—C4—C22—C27 | −158.4 (2) |
C2—C3—C4—C20 | 77.5 (2) | C3—C4—C22—C27 | 72.8 (3) |
O1—C1—C5—C6 | 24.6 (3) | O1—C4—C22—C23 | 144.0 (2) |
C2—C1—C5—C6 | −94.9 (3) | C20—C4—C22—C23 | 24.7 (3) |
O1—C1—C5—C10 | −156.77 (19) | C3—C4—C22—C23 | −104.1 (2) |
C2—C1—C5—C10 | 83.8 (2) | C27—C22—C23—C24 | 1.2 (4) |
C10—C5—C6—C7 | −0.9 (4) | C4—C22—C23—C24 | 178.2 (2) |
C1—C5—C6—C7 | 177.8 (2) | C22—C23—C24—C25 | 0.4 (4) |
C5—C6—C7—C8 | −0.4 (4) | C23—C24—C25—C26 | −1.7 (4) |
C6—C7—C8—C9 | 1.1 (4) | C24—C25—C26—C27 | 1.4 (4) |
C6—C7—C8—Br1 | −177.64 (19) | C25—C26—C27—C22 | 0.2 (4) |
C7—C8—C9—C10 | −0.6 (4) | C23—C22—C27—C26 | −1.5 (4) |
Br1—C8—C9—C10 | 178.21 (19) | C4—C22—C27—C26 | −178.5 (2) |
C8—C9—C10—C5 | −0.7 (4) | C5—C1—O1—C4 | −160.22 (17) |
C6—C5—C10—C9 | 1.4 (4) | C2—C1—O1—C4 | −33.8 (2) |
C1—C5—C10—C9 | −177.3 (2) | C22—C4—O1—C1 | 163.18 (16) |
C13—C2—C11—O6 | −158.5 (2) | C20—C4—O1—C1 | −73.3 (2) |
C3—C2—C11—O6 | −32.1 (3) | C3—C4—O1—C1 | 44.22 (19) |
C1—C2—C11—O6 | 80.9 (3) | O3—C13—O2—C14 | −165.6 (2) |
C13—C2—C11—C12 | 23.4 (3) | C2—C13—O2—C14 | 19.3 (3) |
C3—C2—C11—C12 | 149.8 (2) | C19—C14—O2—C13 | 0.8 (3) |
C1—C2—C11—C12 | −97.2 (2) | C15—C14—O2—C13 | 179.2 (2) |
C3—C2—C13—O3 | 150.0 (2) | O4—C20—O5—C21 | 3.2 (3) |
C11—C2—C13—O3 | −85.9 (3) | C4—C20—O5—C21 | 177.52 (19) |
C1—C2—C13—O3 | 35.8 (3) | C33—C28—C29—C30 | 1.3 (4) |
C3—C2—C13—O2 | −35.2 (3) | C34—C28—C29—C30 | −177.0 (3) |
C11—C2—C13—O2 | 89.0 (2) | C28—C29—C30—C31 | −0.8 (5) |
C1—C2—C13—O2 | −149.32 (19) | C29—C30—C31—C32 | −0.1 (4) |
C19—C14—C15—C16 | −0.2 (4) | C29—C30—C31—C35 | 179.6 (3) |
O2—C14—C15—C16 | −178.6 (2) | C30—C31—C32—C33 | 0.3 (4) |
C14—C15—C16—C17 | −0.9 (4) | C35—C31—C32—C33 | −179.4 (3) |
C15—C16—C17—C18 | 0.6 (4) | C29—C28—C33—C32 | −1.1 (4) |
C16—C17—C18—C19 | 0.9 (4) | C34—C28—C33—C32 | 177.2 (3) |
C15—C14—C19—C18 | 1.6 (3) | C31—C32—C33—C28 | 0.3 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O3 | 0.98 | 2.45 | 2.829 (3) | 103 |
C3—H3···O6 | 0.98 | 2.23 | 2.765 (3) | 113 |
C6—H6···O6i | 0.93 | 2.57 | 3.289 (3) | 135 |
C12—H12C···O5ii | 0.96 | 2.67 | 3.595 (3) | 162 |
C21—H21C···O4iii | 0.96 | 2.73 | 3.660 (4) | 163 |
C25—H25···Br1iv | 0.93 | 3.33 | 4.047 (3) | 135 |
C35—H35B···O3v | 0.96 | 2.83 | 3.523 (4) | 129 |
C24—H24···Cg1v | 0.93 | 2.94 | 3.579 (3) | 127 |
C35—H35C···Cg2vi | 0.96 | 2.95 | 3.764 (4) | 143 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1, y, z; (iii) −x+1, −y+1, −z+2; (iv) x−1, y+1, z; (v) x−1, y, z; (vi) −x+1, −y, −z+2. |
Isostructurality indices calculated for solvates (Ia)–(Ic) topSolvates | Π | A | Iv(max) (%) |
(Ia)–(Ib) | 0.004 | 1.16 | 98.3 |
(Ia)–(Ic) | 0.017 | 0.97 | 96.8 |
(Ib)–(Ic) | 0.013 | 1.34 | 98.6 |
Π is the unit-cell similarity descriptor, A is the aspericity index and
Iv is the volumetric isostructurality index. |
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