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Isostructurality is more likely to occur in multicomponent systems. In this context, three closely related solvates were crystallized, namely, benzene (C27H21BrO6·C6H6), toluene (C27H21BrO6·C7H8) and xylene (C27H21BrO6·C8H10) with methyl 3a-acetyl-3-(4-bromo­phen­yl)-4-oxo-1-phenyl-3,3a,4,9b-tetra­hydro-1H-furo[3,4-c]chromene-1-carboxyl­ate, and their crystal structures determined. All three structures belong to the same space group (P\overline{1}) 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617005940/lg3203sup1.cif
Contains datablocks Ia, Ib, Ic, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617005940/lg3203Iasup2.hkl
Contains datablock Ia

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617005940/lg3203Iasup5.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617005940/lg3203Ibsup3.hkl
Contains datablock Ib

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617005940/lg3203Ibsup6.cml
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617005940/lg3203Icsup4.hkl
Contains datablock Ic

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229617005940/lg3203Icsup7.cml
Supplementary material

CCDC references: 1544953; 1544952; 1544951

Computing details top

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-1H-furo[3,4-c]chromene-1-carboxylate benzene monosolvate top
Crystal data top
C27H21BrO6·C6H6Z = 2
Mr = 599.45F(000) = 616
Triclinic, P1Dx = 1.404 Mg m3
a = 8.4269 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.4905 (8) ÅCell parameters from 5828 reflections
c = 15.1415 (10) Åθ = 2.5–27.0°
α = 66.530 (1)°µ = 1.49 mm1
β = 76.005 (1)°T = 294 K
γ = 85.473 (1)°Block, colourless
V = 1418.22 (17) Å30.19 × 0.17 × 0.09 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4034 reflections with I > 2σ(I)
ω scansRint = 0.021
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
θmax = 25.0°, θmin = 1.8°
Tmin = 0.73, Tmax = 0.86h = 1010
13730 measured reflectionsk = 1414
4968 independent reflectionsl = 1717
Refinement top
Refinement on F284 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-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 reflectionsΔρmax = 0.18 e Å3
394 parametersΔρmin = 0.43 e Å3
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
xyzUiso*/UeqOcc. (<1)
Br10.71066 (4)0.03317 (2)0.02574 (2)0.08946 (14)
C10.3530 (2)0.32188 (15)0.25923 (13)0.0411 (4)
H10.31160.26950.32840.049*
C20.4685 (2)0.41756 (15)0.25658 (12)0.0392 (4)
C30.3672 (2)0.52833 (15)0.22766 (13)0.0391 (4)
H30.40060.56700.15540.047*
C40.1907 (2)0.48226 (15)0.25115 (13)0.0400 (4)
C50.4286 (2)0.24895 (15)0.20183 (13)0.0410 (4)
C60.4169 (2)0.27581 (17)0.10605 (14)0.0502 (5)
H60.35500.33900.07610.060*
C70.4956 (3)0.21056 (18)0.05407 (15)0.0557 (5)
H70.48480.22810.00990.067*
C80.5906 (3)0.11898 (17)0.09802 (16)0.0533 (5)
C90.6021 (3)0.08925 (18)0.19359 (17)0.0585 (5)
H90.66500.02650.22300.070*
C100.5196 (3)0.15328 (17)0.24564 (15)0.0529 (5)
H100.52500.13220.31110.064*
C110.6311 (2)0.43505 (16)0.17643 (14)0.0433 (4)
C120.7808 (2)0.3763 (2)0.20661 (18)0.0632 (6)
H12A0.87130.39830.15000.095*
H12B0.76380.29330.23380.095*
H12C0.80400.39950.25560.095*
C130.5078 (2)0.38161 (17)0.35695 (14)0.0463 (4)
C140.4924 (2)0.58193 (17)0.33889 (13)0.0458 (4)
C150.5353 (2)0.6593 (2)0.37419 (15)0.0547 (5)
H150.59580.63480.42240.066*
C160.4869 (3)0.7730 (2)0.33668 (17)0.0620 (6)
H160.51390.82590.36010.074*
C170.3986 (3)0.80925 (19)0.26454 (18)0.0623 (6)
H170.36620.88640.23940.075*
C180.3580 (2)0.73048 (17)0.22958 (16)0.0528 (5)
H180.29950.75560.18030.063*
C190.4035 (2)0.61427 (16)0.26715 (13)0.0428 (4)
C200.1118 (2)0.43328 (16)0.36296 (14)0.0431 (4)
C210.1229 (3)0.3376 (2)0.48447 (15)0.0646 (6)
H21A0.06220.27310.51990.097*
H21B0.22880.31030.48850.097*
H21C0.13530.39480.51310.097*
C220.0860 (2)0.57072 (16)0.18908 (13)0.0416 (4)
C230.0302 (2)0.63540 (18)0.22736 (15)0.0540 (5)
H230.04900.62250.29390.065*
C240.1181 (3)0.71878 (19)0.16770 (17)0.0645 (6)
H240.19530.76180.19430.077*
C250.0926 (3)0.7386 (2)0.06993 (18)0.0693 (6)
H250.15370.79370.03020.083*
C260.0239 (3)0.6763 (2)0.03084 (18)0.0741 (7)
H260.04340.69060.03610.089*
C270.1126 (3)0.59251 (19)0.09005 (15)0.0575 (5)
H270.19080.55060.06280.069*
O10.21818 (14)0.38523 (10)0.22171 (9)0.0419 (3)
O20.54167 (16)0.46704 (12)0.38354 (9)0.0509 (3)
O30.52138 (19)0.28245 (13)0.41112 (10)0.0609 (4)
O40.17949 (18)0.42882 (15)0.42482 (10)0.0649 (4)
O50.03573 (16)0.38974 (14)0.38158 (10)0.0576 (4)
O60.63060 (18)0.49466 (14)0.09211 (11)0.0659 (4)
C280.0169 (9)0.1041 (4)0.3275 (7)0.115 (3)0.683 (13)
H280.02530.17710.31360.138*0.683 (13)
C290.0485 (6)0.0448 (7)0.2668 (4)0.142 (3)0.683 (13)
H290.13460.07810.21230.170*0.683 (13)
C300.0147 (8)0.0643 (7)0.2875 (7)0.134 (3)0.683 (13)
H300.02910.10400.24690.161*0.683 (13)
C310.1434 (9)0.1141 (3)0.3690 (8)0.111 (3)0.683 (13)
H310.18570.18710.38280.133*0.683 (13)
C320.2088 (6)0.0548 (8)0.4297 (4)0.123 (3)0.683 (13)
H320.29490.08810.48420.148*0.683 (13)
C330.1456 (9)0.0543 (8)0.4090 (6)0.132 (3)0.683 (13)
H330.18940.09400.44960.158*0.683 (13)
C2810.0176 (17)0.0924 (11)0.2812 (11)0.106 (5)0.317 (13)
H2810.08480.15600.23680.128*0.317 (13)
C2910.0160 (16)0.0066 (15)0.2609 (6)0.115 (6)0.317 (13)
H2910.08220.00930.20300.138*0.317 (13)
C3010.084 (2)0.1017 (8)0.3272 (9)0.089 (5)0.317 (13)
H3010.08550.16800.31360.106*0.317 (13)
C3110.1833 (17)0.0977 (10)0.4137 (7)0.087 (5)0.317 (13)
H3110.25050.16120.45810.104*0.317 (13)
C3210.1817 (17)0.0014 (14)0.4340 (8)0.110 (5)0.317 (13)
H3210.24790.00410.49190.132*0.317 (13)
C3310.081 (2)0.0965 (7)0.3677 (13)0.109 (6)0.317 (13)
H3310.08020.16270.38130.131*0.317 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.1075 (2)0.06487 (19)0.0935 (2)0.02903 (15)0.00588 (16)0.04336 (16)
C10.0437 (10)0.0374 (9)0.0375 (9)0.0005 (7)0.0087 (7)0.0103 (8)
C20.0418 (9)0.0399 (9)0.0348 (9)0.0012 (7)0.0083 (7)0.0140 (7)
C30.0399 (9)0.0394 (9)0.0355 (9)0.0007 (7)0.0045 (7)0.0145 (7)
C40.0404 (9)0.0410 (9)0.0388 (9)0.0003 (7)0.0044 (7)0.0183 (8)
C50.0443 (10)0.0323 (9)0.0433 (10)0.0007 (7)0.0112 (8)0.0108 (8)
C60.0582 (12)0.0414 (10)0.0474 (11)0.0139 (9)0.0150 (9)0.0146 (9)
C70.0666 (13)0.0509 (12)0.0486 (11)0.0107 (10)0.0118 (10)0.0211 (9)
C80.0576 (12)0.0368 (10)0.0634 (13)0.0044 (9)0.0073 (10)0.0219 (9)
C90.0622 (13)0.0397 (11)0.0753 (15)0.0152 (9)0.0258 (11)0.0212 (10)
C100.0650 (12)0.0425 (11)0.0529 (11)0.0082 (9)0.0242 (10)0.0155 (9)
C110.0426 (10)0.0444 (10)0.0453 (11)0.0001 (8)0.0070 (8)0.0216 (9)
C120.0445 (11)0.0815 (16)0.0688 (14)0.0086 (10)0.0110 (10)0.0372 (12)
C130.0466 (10)0.0520 (12)0.0397 (10)0.0002 (9)0.0089 (8)0.0176 (9)
C140.0443 (10)0.0515 (11)0.0382 (10)0.0066 (8)0.0013 (8)0.0189 (9)
C150.0521 (11)0.0681 (14)0.0457 (11)0.0155 (10)0.0009 (9)0.0281 (10)
C160.0614 (13)0.0640 (14)0.0665 (14)0.0170 (11)0.0031 (11)0.0386 (12)
C170.0603 (13)0.0466 (12)0.0776 (15)0.0073 (10)0.0005 (11)0.0297 (11)
C180.0503 (11)0.0472 (11)0.0585 (12)0.0028 (9)0.0064 (9)0.0211 (10)
C190.0390 (9)0.0445 (10)0.0421 (10)0.0051 (8)0.0015 (8)0.0193 (8)
C200.0396 (10)0.0448 (10)0.0432 (10)0.0012 (8)0.0051 (8)0.0179 (8)
C210.0486 (12)0.0826 (16)0.0467 (12)0.0088 (11)0.0020 (9)0.0145 (11)
C220.0390 (9)0.0425 (10)0.0428 (10)0.0015 (7)0.0061 (8)0.0183 (8)
C230.0575 (12)0.0532 (12)0.0477 (11)0.0092 (9)0.0037 (9)0.0225 (9)
C240.0583 (13)0.0568 (13)0.0704 (15)0.0193 (10)0.0050 (11)0.0255 (11)
C250.0734 (15)0.0631 (14)0.0705 (15)0.0248 (12)0.0283 (12)0.0228 (12)
C260.0976 (18)0.0767 (16)0.0536 (13)0.0312 (14)0.0296 (13)0.0297 (12)
C270.0649 (13)0.0607 (13)0.0501 (12)0.0212 (10)0.0145 (10)0.0277 (10)
O10.0398 (6)0.0417 (7)0.0478 (7)0.0043 (5)0.0113 (5)0.0211 (6)
O20.0604 (8)0.0541 (8)0.0414 (7)0.0021 (6)0.0151 (6)0.0193 (6)
O30.0818 (10)0.0513 (9)0.0492 (8)0.0060 (7)0.0276 (7)0.0131 (7)
O40.0581 (9)0.0927 (12)0.0432 (8)0.0203 (8)0.0051 (7)0.0257 (8)
O50.0430 (8)0.0774 (10)0.0428 (7)0.0120 (7)0.0042 (6)0.0144 (7)
O60.0600 (9)0.0755 (10)0.0434 (8)0.0077 (7)0.0021 (6)0.0130 (8)
C280.082 (6)0.081 (4)0.182 (10)0.003 (3)0.047 (6)0.041 (5)
C290.081 (4)0.067 (6)0.263 (8)0.006 (4)0.033 (4)0.055 (5)
C300.076 (5)0.071 (6)0.251 (10)0.007 (4)0.054 (5)0.049 (7)
C310.086 (6)0.072 (4)0.169 (9)0.000 (3)0.072 (6)0.016 (5)
C320.148 (6)0.069 (7)0.146 (6)0.017 (5)0.078 (4)0.007 (4)
C330.157 (8)0.078 (7)0.159 (8)0.026 (5)0.073 (6)0.019 (6)
C2810.083 (9)0.070 (9)0.169 (13)0.007 (7)0.049 (8)0.039 (8)
C2910.095 (10)0.073 (13)0.143 (9)0.019 (8)0.025 (7)0.013 (8)
C3010.082 (13)0.060 (7)0.108 (9)0.008 (6)0.017 (7)0.018 (6)
C3110.138 (11)0.052 (8)0.076 (7)0.006 (8)0.044 (6)0.020 (6)
C3210.143 (13)0.067 (13)0.122 (10)0.012 (9)0.047 (7)0.026 (10)
C3310.111 (17)0.054 (7)0.143 (13)0.013 (7)0.037 (10)0.010 (8)
Geometric parameters (Å, º) top
Br1—C81.897 (2)C20—O41.191 (2)
C1—O11.432 (2)C20—O51.318 (2)
C1—C51.504 (2)C21—O51.451 (2)
C1—C21.582 (2)C21—H21A0.9600
C1—H10.9800C21—H21B0.9600
C2—C131.516 (2)C21—H21C0.9600
C2—C31.532 (2)C22—C271.376 (3)
C2—C111.559 (2)C22—C231.386 (3)
C3—C191.501 (2)C23—C241.379 (3)
C3—C41.545 (2)C23—H230.9300
C3—H30.9800C24—C251.364 (3)
C4—O11.434 (2)C24—H240.9300
C4—C221.518 (3)C25—C261.373 (3)
C4—C201.542 (2)C25—H250.9300
C5—C61.379 (3)C26—C271.382 (3)
C5—C101.388 (3)C26—H260.9300
C6—C71.377 (3)C27—H270.9300
C6—H60.9300C28—C291.3900
C7—C81.378 (3)C28—C331.3900
C7—H70.9300C28—H280.9300
C8—C91.370 (3)C29—C301.3900
C9—C101.376 (3)C29—H290.9300
C9—H90.9300C30—C311.3900
C10—H100.9300C30—H300.9300
C11—O61.196 (2)C31—C321.3900
C11—C121.484 (3)C31—H310.9300
C12—H12A0.9600C32—C331.3900
C12—H12B0.9600C32—H320.9300
C12—H12C0.9600C33—H330.9300
C13—O31.197 (2)C281—C2911.3900
C13—O21.352 (2)C281—C3311.3900
C14—C191.379 (3)C281—H2810.9300
C14—C151.382 (3)C291—C3011.3900
C14—O21.399 (2)C291—H2910.9300
C15—C161.373 (3)C301—C3111.3900
C15—H150.9300C301—H3010.9300
C16—C171.378 (3)C311—C3211.3900
C16—H160.9300C311—H3110.9300
C17—C181.386 (3)C321—C3311.3900
C17—H170.9300C321—H3210.9300
C18—C191.392 (3)C331—H3310.9300
C18—H180.9300
O1—C1—C5110.25 (14)C14—C19—C18117.21 (18)
O1—C1—C2105.07 (13)C14—C19—C3120.66 (17)
C5—C1—C2116.28 (14)C18—C19—C3122.03 (17)
O1—C1—H1108.3O4—C20—O5124.38 (17)
C5—C1—H1108.3O4—C20—C4124.23 (16)
C2—C1—H1108.3O5—C20—C4111.23 (15)
C13—C2—C3113.78 (15)O5—C21—H21A109.5
C13—C2—C11109.17 (14)O5—C21—H21B109.5
C3—C2—C11109.63 (14)H21A—C21—H21B109.5
C13—C2—C1109.66 (14)O5—C21—H21C109.5
C3—C2—C1102.89 (13)H21A—C21—H21C109.5
C11—C2—C1111.64 (14)H21B—C21—H21C109.5
C19—C3—C2113.31 (14)C27—C22—C23118.47 (18)
C19—C3—C4120.39 (14)C27—C22—C4119.21 (16)
C2—C3—C4104.05 (14)C23—C22—C4122.22 (16)
C19—C3—H3106.0C24—C23—C22120.67 (19)
C2—C3—H3106.0C24—C23—H23119.7
C4—C3—H3106.0C22—C23—H23119.7
O1—C4—C22109.31 (13)C25—C24—C23120.5 (2)
O1—C4—C20107.27 (14)C25—C24—H24119.8
C22—C4—C20113.46 (14)C23—C24—H24119.8
O1—C4—C3101.38 (13)C24—C25—C26119.4 (2)
C22—C4—C3112.24 (14)C24—C25—H25120.3
C20—C4—C3112.32 (14)C26—C25—H25120.3
C6—C5—C10118.55 (18)C25—C26—C27120.6 (2)
C6—C5—C1122.80 (16)C25—C26—H26119.7
C10—C5—C1118.59 (16)C27—C26—H26119.7
C7—C6—C5121.02 (18)C22—C27—C26120.4 (2)
C7—C6—H6119.5C22—C27—H27119.8
C5—C6—H6119.5C26—C27—H27119.8
C6—C7—C8119.16 (19)C1—O1—C4107.60 (12)
C6—C7—H7120.4C13—O2—C14121.68 (14)
C8—C7—H7120.4C20—O5—C21117.18 (15)
C9—C8—C7120.98 (19)C29—C28—C33120.0
C9—C8—Br1118.83 (15)C29—C28—H28120.0
C7—C8—Br1120.18 (16)C33—C28—H28120.0
C8—C9—C10119.30 (18)C28—C29—C30120.0
C8—C9—H9120.3C28—C29—H29120.0
C10—C9—H9120.3C30—C29—H29120.0
C9—C10—C5120.92 (19)C31—C30—C29120.0
C9—C10—H10119.5C31—C30—H30120.0
C5—C10—H10119.5C29—C30—H30120.0
O6—C11—C12122.06 (18)C30—C31—C32120.0
O6—C11—C2118.66 (16)C30—C31—H31120.0
C12—C11—C2119.27 (17)C32—C31—H31120.0
C11—C12—H12A109.5C33—C32—C31120.0
C11—C12—H12B109.5C33—C32—H32120.0
H12A—C12—H12B109.5C31—C32—H32120.0
C11—C12—H12C109.5C32—C33—C28120.0
H12A—C12—H12C109.5C32—C33—H33120.0
H12B—C12—H12C109.5C28—C33—H33120.0
O3—C13—O2117.98 (16)C291—C281—C331120.0
O3—C13—C2124.01 (17)C291—C281—H281120.0
O2—C13—C2117.81 (16)C331—C281—H281120.0
C19—C14—C15122.76 (19)C301—C291—C281120.0
C19—C14—O2122.25 (16)C301—C291—H291120.0
C15—C14—O2114.97 (17)C281—C291—H291120.0
C16—C15—C14118.7 (2)C311—C301—C291120.0
C16—C15—H15120.6C311—C301—H301120.0
C14—C15—H15120.6C291—C301—H301120.0
C15—C16—C17120.5 (2)C301—C311—C321120.0
C15—C16—H16119.8C301—C311—H311120.0
C17—C16—H16119.8C321—C311—H311120.0
C16—C17—C18119.9 (2)C311—C321—C331120.0
C16—C17—H17120.1C311—C321—H321120.0
C18—C17—H17120.1C331—C321—H321120.0
C17—C18—C19121.0 (2)C321—C331—C281120.0
C17—C18—H18119.5C321—C331—H331120.0
C19—C18—H18119.5C281—C331—H331120.0
O1—C1—C2—C13128.41 (15)C15—C14—C19—C3176.90 (17)
C5—C1—C2—C13109.40 (17)O2—C14—C19—C35.0 (3)
O1—C1—C2—C37.02 (16)C17—C18—C19—C141.1 (3)
C5—C1—C2—C3129.21 (15)C17—C18—C19—C3177.39 (17)
O1—C1—C2—C11110.47 (15)C2—C3—C19—C1413.0 (2)
C5—C1—C2—C1111.7 (2)C4—C3—C19—C14110.95 (19)
C13—C2—C3—C1932.6 (2)C2—C3—C19—C18163.17 (16)
C11—C2—C3—C1989.95 (17)C4—C3—C19—C1872.8 (2)
C1—C2—C3—C19151.15 (14)O1—C4—C20—O4109.0 (2)
C13—C2—C3—C499.89 (16)C22—C4—C20—O4130.1 (2)
C11—C2—C3—C4137.55 (14)C3—C4—C20—O41.5 (3)
C1—C2—C3—C418.66 (16)O1—C4—C20—O566.59 (19)
C19—C3—C4—O1166.38 (15)C22—C4—C20—O554.2 (2)
C2—C3—C4—O138.10 (16)C3—C4—C20—O5177.14 (15)
C19—C3—C4—C2277.1 (2)O1—C4—C22—C2739.2 (2)
C2—C3—C4—C22154.63 (14)C20—C4—C22—C27158.89 (17)
C19—C3—C4—C2052.2 (2)C3—C4—C22—C2772.4 (2)
C2—C3—C4—C2076.11 (17)O1—C4—C22—C23144.42 (17)
O1—C1—C5—C624.8 (2)C20—C4—C22—C2324.7 (2)
C2—C1—C5—C694.6 (2)C3—C4—C22—C23103.9 (2)
O1—C1—C5—C10157.95 (16)C27—C22—C23—C240.7 (3)
C2—C1—C5—C1082.6 (2)C4—C22—C23—C24177.08 (19)
C10—C5—C6—C70.9 (3)C22—C23—C24—C250.3 (3)
C1—C5—C6—C7176.30 (18)C23—C24—C25—C261.3 (4)
C5—C6—C7—C81.7 (3)C24—C25—C26—C271.3 (4)
C6—C7—C8—C92.7 (3)C23—C22—C27—C260.6 (3)
C6—C7—C8—Br1176.32 (16)C4—C22—C27—C26177.2 (2)
C7—C8—C9—C101.1 (3)C25—C26—C27—C220.4 (4)
Br1—C8—C9—C10177.95 (16)C5—C1—O1—C4158.87 (13)
C8—C9—C10—C51.6 (3)C2—C1—O1—C432.84 (16)
C6—C5—C10—C92.6 (3)C22—C4—O1—C1163.27 (13)
C1—C5—C10—C9174.76 (18)C20—C4—O1—C173.32 (16)
C13—C2—C11—O6158.34 (18)C3—C4—O1—C144.61 (16)
C3—C2—C11—O633.1 (2)O3—C13—O2—C14164.25 (17)
C1—C2—C11—O680.3 (2)C2—C13—O2—C1420.6 (2)
C13—C2—C11—C1222.4 (2)C19—C14—O2—C131.5 (3)
C3—C2—C11—C12147.69 (17)C15—C14—O2—C13179.74 (16)
C1—C2—C11—C1298.96 (19)O4—C20—O5—C212.8 (3)
C3—C2—C13—O3147.57 (18)C4—C20—O5—C21178.36 (17)
C11—C2—C13—O389.6 (2)C33—C28—C29—C300.0
C1—C2—C13—O333.0 (2)C28—C29—C30—C310.0
C3—C2—C13—O237.6 (2)C29—C30—C31—C320.0
C11—C2—C13—O285.19 (19)C30—C31—C32—C330.0
C1—C2—C13—O2152.21 (15)C31—C32—C33—C280.0
C19—C14—C15—C160.3 (3)C29—C28—C33—C320.0
O2—C14—C15—C16177.87 (17)C331—C281—C291—C3010.0
C14—C15—C16—C170.6 (3)C281—C291—C301—C3110.0
C15—C16—C17—C180.1 (3)C291—C301—C311—C3210.0
C16—C17—C18—C190.8 (3)C301—C311—C321—C3310.0
C15—C14—C19—C180.5 (3)C311—C321—C331—C2810.0
O2—C14—C19—C18178.57 (16)C291—C281—C331—C3210.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O30.982.452.848 (2)104
C3—H3···O60.982.242.766 (2)113
C6—H6···O6i0.932.553.306 (2)139
C12—H12C···O5ii0.962.553.437 (3)153
C21—H21C···O4iii0.962.693.645 (3)174
C25—H25···Br1iv0.933.103.788 (2)132
C24—H24···Cg1v0.933.073.715 (2)128
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z; (iii) x, y+1, z+1; (iv) x1, y+1, z; (v) x1, y, z.
(Ib) Methyl 3a-acetyl-3-(4-bromophenyl)-4-oxo-1-phenyl-3,3a,4,9b-tetrahydro-1H-furo[3,4-c]chromene-1-carboxylate toluene monosolvate top
Crystal data top
C27H21BrO6·C7H8Z = 2
Mr = 613.48F(000) = 632
Triclinic, P1Dx = 1.418 Mg m3
a = 8.3989 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.5415 (7) ÅCell parameters from 6899 reflections
c = 15.2195 (8) Åθ = 2.5–28.2°
α = 67.408 (1)°µ = 1.48 mm1
β = 76.135 (1)°T = 294 K
γ = 85.458 (1)°Block, colourless
V = 1436.85 (14) Å30.15 × 0.14 × 0.08 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
4218 reflections with I > 2σ(I)
ω scansRint = 0.025
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
θmax = 25.0°, θmin = 1.8°
Tmin = 0.81, Tmax = 0.87h = 99
13909 measured reflectionsk = 1414
5042 independent reflectionsl = 1818
Refinement top
Refinement on F244 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-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 reflectionsΔρmax = 0.31 e Å3
414 parametersΔρmin = 0.52 e Å3
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
xyzUiso*/UeqOcc. (<1)
Br10.70977 (4)0.53459 (2)0.02432 (2)0.08892 (15)
C10.3639 (2)0.82859 (16)0.25646 (13)0.0406 (4)
H10.32360.77730.32470.049*
C20.4789 (2)0.92385 (16)0.25442 (13)0.0391 (4)
C30.3749 (2)1.03263 (16)0.22863 (13)0.0386 (4)
H30.40711.07170.15740.046*
C40.1985 (2)0.98640 (16)0.25129 (13)0.0392 (4)
C50.4385 (2)0.75524 (15)0.19896 (13)0.0405 (4)
C60.4245 (3)0.78120 (18)0.10441 (15)0.0503 (5)
H60.36330.84440.07510.060*
C70.5005 (3)0.71413 (19)0.05281 (16)0.0554 (5)
H70.48880.73080.01030.067*
C80.5940 (3)0.62223 (18)0.09633 (17)0.0530 (5)
C90.6086 (3)0.59411 (18)0.19030 (18)0.0559 (5)
H90.67110.53140.21910.067*
C100.5293 (3)0.66029 (17)0.24162 (16)0.0508 (5)
H100.53690.64090.30590.061*
C110.6396 (2)0.94189 (17)0.17339 (14)0.0433 (4)
C120.7916 (3)0.8834 (2)0.20103 (18)0.0600 (6)
H12A0.81900.90800.24810.090*
H12B0.88000.90320.14400.090*
H12C0.77380.80130.22880.090*
C130.5209 (2)0.88773 (18)0.35312 (14)0.0451 (4)
C140.5003 (2)1.08466 (17)0.34062 (13)0.0443 (4)
C150.5419 (3)1.1612 (2)0.37770 (15)0.0516 (5)
H150.60281.13690.42540.062*
C160.4916 (3)1.2731 (2)0.34284 (17)0.0593 (6)
H160.51771.32520.36740.071*
C170.4025 (3)1.3093 (2)0.27152 (19)0.0615 (6)
H170.36891.38550.24810.074*
C180.3631 (3)1.23191 (18)0.23487 (16)0.0520 (5)
H180.30421.25710.18620.062*
C190.4103 (2)1.11717 (16)0.26971 (13)0.0415 (4)
C200.1205 (2)0.93700 (16)0.36169 (14)0.0418 (4)
C210.1135 (3)0.8449 (2)0.48247 (16)0.0624 (6)
H21A0.13250.90290.51030.094*
H21B0.04730.78510.51720.094*
H21C0.21660.81240.48740.094*
C220.0922 (2)1.07312 (16)0.19073 (14)0.0408 (4)
C230.0269 (3)1.13585 (18)0.22947 (16)0.0514 (5)
H230.04681.12280.29560.062*
C240.1166 (3)1.2175 (2)0.17097 (18)0.0610 (6)
H240.19651.25890.19800.073*
C250.0885 (3)1.2379 (2)0.07349 (19)0.0664 (6)
H250.15021.29200.03440.080*
C260.0320 (3)1.1777 (2)0.03385 (18)0.0693 (7)
H260.05301.19230.03260.083*
C270.1218 (3)1.09576 (19)0.09191 (15)0.0540 (5)
H270.20271.05550.06430.065*
O10.22721 (15)0.89039 (11)0.22049 (9)0.0421 (3)
O20.55257 (17)0.97151 (12)0.38210 (10)0.0490 (3)
O30.5385 (2)0.78954 (13)0.40401 (11)0.0607 (4)
O40.19142 (19)0.92986 (15)0.42306 (10)0.0623 (4)
O50.02914 (17)0.89652 (14)0.38036 (10)0.0554 (4)
O60.6354 (2)1.00079 (15)0.09091 (11)0.0655 (4)
C280.1630 (8)0.5160 (4)0.4190 (4)0.088 (2)0.596 (12)
C290.1734 (9)0.4123 (3)0.4073 (5)0.097 (2)0.596 (12)
H290.24110.35280.45550.117*0.596 (12)
C300.0827 (12)0.3976 (6)0.3235 (7)0.111 (4)0.596 (12)
H300.08960.32820.31570.133*0.596 (12)
C310.0186 (10)0.4865 (9)0.2515 (5)0.159 (5)0.596 (12)
H310.07930.47660.19550.190*0.596 (12)
C320.0290 (8)0.5901 (8)0.2632 (4)0.204 (8)0.596 (12)
H320.09670.64960.21500.245*0.596 (12)
C330.0617 (9)0.6049 (4)0.3469 (5)0.082 (2)0.596 (12)
H330.05480.67420.35480.099*0.596 (12)
C340.2455 (16)0.5362 (11)0.5014 (8)0.152 (4)0.596 (12)
H34A0.35760.51090.51850.229*0.596 (12)
H34B0.24190.61740.48820.229*0.596 (12)
H34C0.19430.49440.55460.229*0.596 (12)
C2810.1523 (15)0.4801 (14)0.4037 (7)0.148 (7)0.404 (12)
C2910.1161 (13)0.4042 (7)0.3552 (11)0.101 (4)0.404 (12)
H2910.16540.33130.38330.121*0.404 (12)
C3010.0062 (15)0.4372 (7)0.2648 (11)0.114 (4)0.404 (12)
H3010.01800.38630.23230.137*0.404 (12)
C3110.0674 (10)0.5461 (7)0.2228 (7)0.112 (4)0.404 (12)
H3110.14100.56820.16230.135*0.404 (12)
C3210.0312 (13)0.6221 (6)0.2713 (9)0.103 (4)0.404 (12)
H3210.08050.69500.24330.124*0.404 (12)
C3310.0787 (18)0.5891 (13)0.3618 (9)0.219 (17)0.404 (12)
H3310.10290.63990.39420.263*0.404 (12)
C3410.2644 (17)0.453 (2)0.4912 (10)0.184 (12)0.404 (12)
H34D0.34270.39760.49620.276*0.404 (12)
H34E0.32010.52120.49490.276*0.404 (12)
H34F0.20900.41990.54380.276*0.404 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.1072 (3)0.0690 (2)0.0940 (2)0.02882 (16)0.00750 (17)0.04884 (17)
C10.0432 (10)0.0388 (10)0.0375 (9)0.0040 (8)0.0099 (8)0.0119 (8)
C20.0416 (10)0.0404 (10)0.0356 (9)0.0044 (8)0.0098 (7)0.0149 (8)
C30.0395 (9)0.0395 (9)0.0347 (9)0.0035 (7)0.0061 (7)0.0138 (7)
C40.0398 (9)0.0402 (10)0.0402 (9)0.0029 (8)0.0072 (8)0.0194 (8)
C50.0431 (10)0.0338 (9)0.0431 (10)0.0013 (8)0.0096 (8)0.0130 (8)
C60.0586 (12)0.0438 (11)0.0459 (11)0.0133 (9)0.0143 (9)0.0152 (9)
C70.0704 (14)0.0514 (12)0.0450 (11)0.0106 (10)0.0127 (10)0.0210 (9)
C80.0558 (12)0.0395 (11)0.0637 (13)0.0061 (9)0.0072 (10)0.0244 (10)
C90.0596 (13)0.0390 (11)0.0722 (15)0.0159 (9)0.0244 (11)0.0216 (10)
C100.0600 (12)0.0416 (11)0.0518 (12)0.0080 (9)0.0229 (10)0.0141 (9)
C110.0433 (10)0.0449 (11)0.0449 (11)0.0010 (8)0.0072 (8)0.0220 (9)
C120.0429 (11)0.0757 (15)0.0686 (14)0.0094 (10)0.0132 (10)0.0364 (12)
C130.0465 (11)0.0511 (12)0.0387 (10)0.0052 (9)0.0117 (8)0.0177 (9)
C140.0425 (10)0.0501 (11)0.0377 (9)0.0037 (8)0.0004 (8)0.0183 (8)
C150.0483 (11)0.0648 (14)0.0457 (11)0.0095 (10)0.0033 (9)0.0276 (10)
C160.0584 (13)0.0616 (14)0.0655 (14)0.0120 (11)0.0007 (11)0.0376 (12)
C170.0627 (14)0.0459 (12)0.0773 (16)0.0037 (10)0.0071 (12)0.0291 (11)
C180.0508 (11)0.0454 (11)0.0598 (12)0.0002 (9)0.0112 (10)0.0207 (10)
C190.0381 (9)0.0440 (10)0.0409 (10)0.0029 (8)0.0022 (8)0.0179 (8)
C200.0403 (10)0.0430 (10)0.0429 (10)0.0032 (8)0.0078 (8)0.0186 (8)
C210.0495 (12)0.0774 (16)0.0482 (12)0.0078 (11)0.0001 (10)0.0155 (11)
C220.0387 (9)0.0408 (10)0.0440 (10)0.0033 (8)0.0092 (8)0.0180 (8)
C230.0547 (12)0.0505 (12)0.0479 (11)0.0092 (9)0.0062 (9)0.0222 (9)
C240.0543 (12)0.0568 (13)0.0685 (15)0.0189 (10)0.0093 (11)0.0262 (11)
C250.0702 (15)0.0601 (14)0.0691 (15)0.0230 (12)0.0283 (12)0.0216 (12)
C260.0904 (18)0.0718 (16)0.0495 (12)0.0267 (14)0.0269 (12)0.0255 (11)
C270.0608 (13)0.0574 (13)0.0470 (11)0.0189 (10)0.0144 (10)0.0253 (10)
O10.0419 (7)0.0418 (7)0.0486 (7)0.0073 (5)0.0137 (6)0.0227 (6)
O20.0577 (8)0.0528 (8)0.0416 (7)0.0031 (6)0.0179 (6)0.0196 (6)
O30.0823 (11)0.0510 (9)0.0523 (8)0.0109 (8)0.0321 (8)0.0152 (7)
O40.0551 (9)0.0886 (12)0.0428 (8)0.0160 (8)0.0074 (7)0.0232 (8)
O50.0427 (8)0.0716 (10)0.0443 (8)0.0093 (7)0.0066 (6)0.0136 (7)
O60.0612 (9)0.0767 (11)0.0413 (8)0.0107 (8)0.0009 (7)0.0120 (8)
C280.083 (4)0.064 (4)0.115 (5)0.022 (3)0.051 (4)0.021 (4)
C290.110 (6)0.070 (4)0.150 (6)0.031 (3)0.082 (5)0.056 (4)
C300.117 (8)0.110 (6)0.120 (6)0.042 (5)0.062 (5)0.046 (5)
C310.107 (6)0.153 (10)0.191 (8)0.009 (8)0.089 (5)0.006 (7)
C320.167 (14)0.176 (10)0.290 (19)0.025 (9)0.169 (14)0.046 (10)
C330.086 (5)0.067 (4)0.085 (4)0.002 (3)0.029 (4)0.012 (3)
C340.169 (10)0.139 (9)0.181 (10)0.062 (8)0.094 (8)0.074 (9)
C2810.125 (12)0.175 (16)0.174 (12)0.066 (11)0.084 (10)0.081 (12)
C2910.070 (6)0.091 (7)0.147 (10)0.019 (5)0.051 (6)0.038 (6)
C3010.086 (7)0.081 (6)0.180 (11)0.012 (5)0.029 (6)0.055 (7)
C3110.077 (6)0.069 (6)0.192 (10)0.016 (4)0.039 (6)0.048 (6)
C3210.066 (6)0.077 (6)0.157 (11)0.001 (4)0.023 (7)0.035 (6)
C3310.19 (2)0.062 (8)0.39 (4)0.033 (11)0.20 (3)0.011 (14)
C3410.116 (10)0.22 (2)0.119 (12)0.057 (13)0.038 (9)0.055 (14)
Geometric parameters (Å, º) top
Br1—C81.897 (2)C21—H21A0.9600
C1—O11.433 (2)C21—H21B0.9600
C1—C51.506 (3)C21—H21C0.9600
C1—C21.581 (3)C22—C271.381 (3)
C1—H10.9800C22—C231.385 (3)
C2—C131.514 (3)C23—C241.381 (3)
C2—C31.531 (2)C23—H230.9300
C2—C111.559 (3)C24—C251.368 (4)
C3—C191.501 (3)C24—H240.9300
C3—C41.545 (3)C25—C261.377 (4)
C3—H30.9800C25—H250.9300
C4—O11.436 (2)C26—C271.380 (3)
C4—C221.516 (3)C26—H260.9300
C4—C201.541 (3)C27—H270.9300
C5—C61.380 (3)C28—C341.386 (11)
C5—C101.386 (3)C28—C291.3900
C6—C71.384 (3)C28—C331.3900
C6—H60.9300C29—C301.3900
C7—C81.379 (3)C29—H290.9300
C7—H70.9300C30—C311.3900
C8—C91.369 (3)C30—H300.9300
C9—C101.380 (3)C31—C321.3900
C9—H90.9300C31—H310.9300
C10—H100.9300C32—C331.3900
C11—O61.195 (2)C32—H320.9300
C11—C121.489 (3)C33—H330.9300
C12—H12A0.9600C34—H34A0.9600
C12—H12B0.9600C34—H34B0.9600
C12—H12C0.9600C34—H34C0.9600
C13—O31.197 (2)C281—C3411.369 (13)
C13—O21.351 (2)C281—C2911.3900
C14—C191.381 (3)C281—C3311.3900
C14—C151.388 (3)C291—C3011.3900
C14—O21.397 (2)C291—H2910.9300
C15—C161.368 (3)C301—C3111.3900
C15—H150.9300C301—H3010.9300
C16—C171.379 (4)C311—C3211.3900
C16—H160.9300C311—H3110.9300
C17—C181.385 (3)C321—C3311.3900
C17—H170.9300C321—H3210.9300
C18—C191.390 (3)C331—H3310.9300
C18—H180.9300C341—H34D0.9600
C20—O41.196 (2)C341—H34E0.9600
C20—O51.318 (2)C341—H34F0.9600
C21—O51.452 (3)
O1—C1—C5110.04 (15)O5—C21—H21A109.5
O1—C1—C2105.20 (14)O5—C21—H21B109.5
C5—C1—C2116.85 (15)H21A—C21—H21B109.5
O1—C1—H1108.1O5—C21—H21C109.5
C5—C1—H1108.1H21A—C21—H21C109.5
C2—C1—H1108.1H21B—C21—H21C109.5
C13—C2—C3113.88 (15)C27—C22—C23118.52 (18)
C13—C2—C11109.69 (15)C27—C22—C4118.92 (17)
C3—C2—C11109.73 (15)C23—C22—C4122.43 (17)
C13—C2—C1109.30 (15)C24—C23—C22120.7 (2)
C3—C2—C1102.86 (14)C24—C23—H23119.6
C11—C2—C1111.24 (15)C22—C23—H23119.6
C19—C3—C2113.31 (15)C25—C24—C23120.4 (2)
C19—C3—C4120.42 (15)C25—C24—H24119.8
C2—C3—C4104.29 (14)C23—C24—H24119.8
C19—C3—H3105.9C24—C25—C26119.4 (2)
C2—C3—H3105.9C24—C25—H25120.3
C4—C3—H3105.9C26—C25—H25120.3
O1—C4—C22109.02 (14)C25—C26—C27120.6 (2)
O1—C4—C20106.93 (14)C25—C26—H26119.7
C22—C4—C20113.83 (15)C27—C26—H26119.7
O1—C4—C3101.45 (14)C26—C27—C22120.4 (2)
C22—C4—C3112.32 (15)C26—C27—H27119.8
C20—C4—C3112.35 (15)C22—C27—H27119.8
C6—C5—C10118.85 (18)C1—O1—C4107.49 (13)
C6—C5—C1122.54 (17)C13—O2—C14121.57 (15)
C10—C5—C1118.58 (17)C20—O5—C21116.85 (16)
C5—C6—C7120.66 (19)C34—C28—C29123.5 (7)
C5—C6—H6119.7C34—C28—C33116.4 (7)
C7—C6—H6119.7C29—C28—C33120.0
C8—C7—C6119.1 (2)C30—C29—C28120.0
C8—C7—H7120.5C30—C29—H29120.0
C6—C7—H7120.5C28—C29—H29120.0
C9—C8—C7121.3 (2)C31—C30—C29120.0
C9—C8—Br1118.82 (16)C31—C30—H30120.0
C7—C8—Br1119.81 (17)C29—C30—H30120.0
C8—C9—C10118.93 (19)C30—C31—C32120.0
C8—C9—H9120.5C30—C31—H31120.0
C10—C9—H9120.5C32—C31—H31120.0
C9—C10—C5121.09 (19)C33—C32—C31120.0
C9—C10—H10119.5C33—C32—H32120.0
C5—C10—H10119.5C31—C32—H32120.0
O6—C11—C12122.38 (19)C32—C33—C28120.0
O6—C11—C2118.59 (17)C32—C33—H33120.0
C12—C11—C2119.01 (17)C28—C33—H33120.0
C11—C12—H12A109.5C28—C34—H34A109.5
C11—C12—H12B109.5C28—C34—H34B109.5
H12A—C12—H12B109.5H34A—C34—H34B109.5
C11—C12—H12C109.5C28—C34—H34C109.5
H12A—C12—H12C109.5H34A—C34—H34C109.5
H12B—C12—H12C109.5H34B—C34—H34C109.5
O3—C13—O2117.93 (17)C341—C281—C291121.8 (15)
O3—C13—C2123.78 (18)C341—C281—C331118.1 (15)
O2—C13—C2118.08 (17)C291—C281—C331120.0
C19—C14—C15122.5 (2)C301—C291—C281120.0
C19—C14—O2122.39 (17)C301—C291—H291120.0
C15—C14—O2115.08 (18)C281—C291—H291120.0
C16—C15—C14118.8 (2)C311—C301—C291120.0
C16—C15—H15120.6C311—C301—H301120.0
C14—C15—H15120.6C291—C301—H301120.0
C15—C16—C17120.5 (2)C301—C311—C321120.0
C15—C16—H16119.7C301—C311—H311120.0
C17—C16—H16119.7C321—C311—H311120.0
C16—C17—C18119.9 (2)C311—C321—C331120.0
C16—C17—H17120.0C311—C321—H321120.0
C18—C17—H17120.0C331—C321—H321120.0
C17—C18—C19121.0 (2)C321—C331—C281120.0
C17—C18—H18119.5C321—C331—H331120.0
C19—C18—H18119.5C281—C331—H331120.0
C14—C19—C18117.22 (18)C281—C341—H34D109.5
C14—C19—C3120.54 (17)C281—C341—H34E109.5
C18—C19—C3122.13 (18)H34D—C341—H34E109.5
O4—C20—O5124.19 (18)C281—C341—H34F109.5
O4—C20—C4123.75 (17)H34D—C341—H34F109.5
O5—C20—C4111.90 (16)H34E—C341—H34F109.5
O1—C1—C2—C13129.03 (15)C17—C18—C19—C141.2 (3)
C5—C1—C2—C13108.59 (18)C17—C18—C19—C3177.60 (19)
O1—C1—C2—C37.70 (17)C2—C3—C19—C1413.5 (2)
C5—C1—C2—C3130.08 (16)C4—C3—C19—C14110.9 (2)
O1—C1—C2—C11109.71 (16)C2—C3—C19—C18162.74 (17)
C5—C1—C2—C1112.7 (2)C4—C3—C19—C1872.9 (2)
C13—C2—C3—C1932.5 (2)O1—C4—C20—O4106.9 (2)
C11—C2—C3—C1990.91 (18)C22—C4—C20—O4132.7 (2)
C1—C2—C3—C19150.62 (15)C3—C4—C20—O43.6 (3)
C13—C2—C3—C4100.26 (17)O1—C4—C20—O568.77 (19)
C11—C2—C3—C4136.36 (15)C22—C4—C20—O551.7 (2)
C1—C2—C3—C417.89 (17)C3—C4—C20—O5179.23 (16)
C19—C3—C4—O1166.01 (15)O1—C4—C22—C2740.6 (2)
C2—C3—C4—O137.48 (16)C20—C4—C22—C27159.83 (18)
C19—C3—C4—C2277.7 (2)C3—C4—C22—C2771.1 (2)
C2—C3—C4—C22153.75 (15)O1—C4—C22—C23143.51 (18)
C19—C3—C4—C2052.1 (2)C20—C4—C22—C2324.2 (3)
C2—C3—C4—C2076.38 (18)C3—C4—C22—C23104.9 (2)
O1—C1—C5—C625.2 (2)C27—C22—C23—C241.3 (3)
C2—C1—C5—C694.6 (2)C4—C22—C23—C24177.29 (19)
O1—C1—C5—C10157.04 (17)C22—C23—C24—C250.2 (4)
C2—C1—C5—C1083.1 (2)C23—C24—C25—C261.1 (4)
C10—C5—C6—C70.4 (3)C24—C25—C26—C271.2 (4)
C1—C5—C6—C7177.35 (19)C25—C26—C27—C220.1 (4)
C5—C6—C7—C81.5 (3)C23—C22—C27—C261.2 (3)
C6—C7—C8—C92.1 (3)C4—C22—C27—C26177.3 (2)
C6—C7—C8—Br1176.33 (17)C5—C1—O1—C4159.79 (14)
C7—C8—C9—C100.7 (3)C2—C1—O1—C433.12 (17)
Br1—C8—C9—C10177.69 (17)C22—C4—O1—C1162.98 (14)
C8—C9—C10—C51.2 (3)C20—C4—O1—C173.55 (17)
C6—C5—C10—C91.8 (3)C3—C4—O1—C144.31 (17)
C1—C5—C10—C9176.06 (19)O3—C13—O2—C14165.03 (18)
C13—C2—C11—O6158.73 (19)C2—C13—O2—C1420.0 (3)
C3—C2—C11—O632.9 (2)C19—C14—O2—C131.6 (3)
C1—C2—C11—O680.2 (2)C15—C14—O2—C13179.97 (17)
C13—C2—C11—C1222.5 (2)O4—C20—O5—C212.8 (3)
C3—C2—C11—C12148.35 (18)C4—C20—O5—C21178.43 (18)
C1—C2—C11—C1298.5 (2)C34—C28—C29—C30178.0 (8)
C3—C2—C13—O3148.3 (2)C33—C28—C29—C300.0
C11—C2—C13—O388.3 (2)C28—C29—C30—C310.0
C1—C2—C13—O333.9 (3)C29—C30—C31—C320.0
C3—C2—C13—O237.0 (2)C30—C31—C32—C330.0
C11—C2—C13—O286.4 (2)C31—C32—C33—C280.0
C1—C2—C13—O2151.37 (16)C34—C28—C33—C32178.2 (7)
C19—C14—C15—C160.1 (3)C29—C28—C33—C320.0
O2—C14—C15—C16178.30 (18)C341—C281—C291—C301177.5 (14)
C14—C15—C16—C170.6 (3)C331—C281—C291—C3010.0
C15—C16—C17—C180.1 (3)C281—C291—C301—C3110.0
C16—C17—C18—C190.8 (3)C291—C301—C311—C3210.0
C15—C14—C19—C180.8 (3)C301—C311—C321—C3310.0
O2—C14—C19—C18179.09 (17)C311—C321—C331—C2810.0
C15—C14—C19—C3177.21 (17)C341—C281—C331—C321177.6 (13)
O2—C14—C19—C34.5 (3)C291—C281—C331—C3210.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O30.982.442.837 (2)104
C3—H3···O60.982.232.766 (2)113
C6—H6···O6i0.932.523.289 (3)140
C12—H12A···O5ii0.962.583.478 (3)155
C21—H21A···O4iii0.962.633.585 (3)176
C25—H25···Br1iv0.933.133.840 (2)134
C24—H24···Cg1v0.933.023.689 (2)123
Symmetry codes: (i) x+1, y+2, z; (ii) x+1, y, z; (iii) x, y+2, z+1; (iv) x1, y+1, z; (v) x1, y, z.
(Ic) Methyl 3a-acetyl-3-(4-bromophenyl)-4-oxo-1-phenyl-3,3a,4,9b-tetrahydro-1H-furo[3,4-c]chromene-1-carboxylate xylene monosolvate top
Crystal data top
C27H21BrO6·C8H10Z = 2
Mr = 627.51F(000) = 648
Triclinic, P1Dx = 1.417 Mg m3
a = 8.2587 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.7841 (9) ÅCell parameters from 4020 reflections
c = 15.6238 (11) Åθ = 2.5–23.1°
α = 66.446 (1)°µ = 1.44 mm1
β = 76.634 (1)°T = 294 K
γ = 86.030 (1)°Block, colourless
V = 1470.67 (18) Å30.18 × 0.16 × 0.01 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3867 reflections with I > 2σ(I)
ω scansRint = 0.025
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
θmax = 25.0°, θmin = 1.7°
Tmin = 0.82, Tmax = 0.96h = 99
14351 measured reflectionsk = 1515
5185 independent reflectionsl = 1818
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-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 reflectionsΔρmax = 0.55 e Å3
383 parametersΔρmin = 0.35 e Å3
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
xyzUiso*/Ueq
Br11.18906 (4)0.04688 (3)0.53253 (3)0.08678 (17)
C10.8692 (3)0.33702 (18)0.75785 (16)0.0399 (5)
H10.82900.28530.82490.048*
C20.9911 (3)0.42971 (18)0.75456 (15)0.0389 (5)
C30.8873 (3)0.53764 (18)0.73159 (15)0.0380 (5)
H30.91880.57940.66200.046*
C40.7064 (3)0.49283 (18)0.75389 (15)0.0379 (5)
C50.9391 (3)0.26627 (18)0.70137 (15)0.0400 (5)
C60.9211 (3)0.2930 (2)0.60977 (17)0.0503 (6)
H60.86010.35610.58110.060*
C70.9928 (3)0.2270 (2)0.55958 (18)0.0552 (7)
H70.97950.24550.49770.066*
C81.0835 (3)0.1344 (2)0.60187 (19)0.0514 (6)
C91.1017 (3)0.1051 (2)0.6937 (2)0.0550 (7)
H91.16260.04180.72210.066*
C101.0291 (3)0.17039 (19)0.74341 (17)0.0476 (6)
H101.04010.15030.80590.057*
C111.1499 (3)0.4488 (2)0.67254 (17)0.0422 (5)
C121.3041 (3)0.3881 (2)0.69551 (19)0.0560 (7)
H12A1.38950.40730.63790.084*
H12B1.28200.30720.72360.084*
H12C1.34070.41040.73990.084*
C131.0381 (3)0.3899 (2)0.85044 (16)0.0448 (6)
C141.0175 (3)0.5811 (2)0.84376 (16)0.0433 (6)
C151.0590 (3)0.6521 (2)0.88319 (17)0.0519 (6)
H151.12060.62520.93020.062*
C161.0079 (3)0.7631 (2)0.8520 (2)0.0600 (7)
H161.03350.81160.87850.072*
C170.9187 (3)0.8024 (2)0.7813 (2)0.0610 (7)
H170.88490.87770.75980.073*
C180.8792 (3)0.7306 (2)0.74233 (19)0.0531 (6)
H180.82030.75860.69400.064*
C190.9257 (3)0.6171 (2)0.77392 (16)0.0411 (5)
C200.6297 (3)0.44175 (19)0.86234 (16)0.0407 (5)
C210.3933 (3)0.3492 (2)0.98211 (17)0.0578 (7)
H21A0.45380.28341.01320.087*
H21B0.28190.32620.98740.087*
H21C0.38950.40221.01210.087*
C220.5985 (3)0.57999 (18)0.69493 (15)0.0393 (5)
C230.4810 (3)0.6416 (2)0.73360 (18)0.0500 (6)
H230.46460.62820.79810.060*
C240.3883 (3)0.7224 (2)0.67726 (19)0.0586 (7)
H240.31040.76350.70380.070*
C250.4109 (4)0.7423 (2)0.5823 (2)0.0644 (8)
H250.34650.79530.54460.077*
C260.5292 (4)0.6834 (2)0.54312 (19)0.0640 (8)
H260.54630.69800.47840.077*
C270.6226 (3)0.6030 (2)0.59879 (17)0.0512 (6)
H270.70260.56390.57130.061*
O10.73120 (18)0.39987 (12)0.72332 (10)0.0413 (4)
O21.0710 (2)0.46945 (14)0.88110 (11)0.0490 (4)
O31.0585 (2)0.29193 (15)0.89781 (12)0.0604 (5)
O40.7052 (2)0.42978 (17)0.92187 (12)0.0641 (5)
O50.47558 (19)0.40353 (15)0.88184 (11)0.0528 (4)
O61.1413 (2)0.51006 (17)0.59264 (12)0.0654 (5)
C280.5034 (3)0.0100 (2)0.76479 (19)0.0600 (7)
C290.4088 (4)0.0818 (3)0.8361 (2)0.0696 (8)
H290.40460.14940.82760.083*
C300.3205 (4)0.0743 (3)0.9200 (2)0.0688 (8)
H300.25670.13710.96650.083*
C310.3241 (3)0.0232 (2)0.93670 (19)0.0598 (7)
C320.4196 (4)0.1132 (2)0.8664 (2)0.0664 (8)
H320.42530.18030.87550.080*
C330.5079 (4)0.1067 (2)0.7821 (2)0.0645 (8)
H330.57210.16940.73590.077*
C340.5929 (4)0.0038 (3)0.6713 (2)0.0899 (10)
H34A0.53250.04500.62280.135*
H34B0.60060.07450.67880.135*
H34C0.70280.03700.65280.135*
C350.2265 (4)0.0314 (3)1.0282 (2)0.0916 (11)
H35A0.11620.00001.04350.137*
H35B0.22010.11001.02000.137*
H35C0.28120.01061.07940.137*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0940 (3)0.0840 (3)0.0987 (3)0.01728 (19)0.0094 (2)0.0619 (2)
C10.0397 (13)0.0417 (13)0.0351 (12)0.0015 (10)0.0085 (10)0.0118 (10)
C20.0378 (12)0.0451 (13)0.0331 (12)0.0035 (10)0.0088 (10)0.0146 (10)
C30.0374 (12)0.0408 (12)0.0321 (11)0.0015 (10)0.0068 (10)0.0112 (10)
C40.0372 (12)0.0421 (13)0.0362 (12)0.0006 (10)0.0074 (10)0.0176 (10)
C50.0395 (13)0.0380 (12)0.0399 (13)0.0020 (10)0.0080 (10)0.0127 (10)
C60.0572 (16)0.0465 (14)0.0450 (14)0.0092 (12)0.0153 (12)0.0149 (12)
C70.0641 (17)0.0591 (16)0.0430 (14)0.0007 (14)0.0075 (12)0.0229 (13)
C80.0470 (14)0.0494 (15)0.0589 (16)0.0023 (12)0.0037 (12)0.0270 (13)
C90.0535 (16)0.0442 (14)0.0688 (18)0.0086 (12)0.0166 (13)0.0232 (13)
C100.0540 (15)0.0433 (14)0.0429 (13)0.0017 (12)0.0161 (12)0.0114 (11)
C110.0416 (14)0.0471 (14)0.0398 (14)0.0020 (11)0.0074 (11)0.0194 (12)
C120.0393 (14)0.0648 (17)0.0630 (16)0.0045 (12)0.0087 (12)0.0264 (14)
C130.0428 (14)0.0540 (16)0.0379 (13)0.0043 (11)0.0110 (11)0.0178 (12)
C140.0366 (12)0.0524 (15)0.0395 (13)0.0030 (11)0.0027 (10)0.0193 (11)
C150.0434 (14)0.0711 (18)0.0449 (14)0.0088 (13)0.0033 (11)0.0285 (13)
C160.0531 (16)0.0705 (19)0.0676 (18)0.0091 (14)0.0039 (14)0.0423 (15)
C170.0604 (17)0.0513 (16)0.0775 (19)0.0011 (13)0.0135 (15)0.0329 (15)
C180.0490 (15)0.0504 (15)0.0616 (16)0.0005 (12)0.0155 (12)0.0220 (13)
C190.0355 (12)0.0472 (14)0.0391 (12)0.0032 (10)0.0040 (10)0.0171 (11)
C200.0377 (13)0.0453 (13)0.0412 (13)0.0025 (10)0.0088 (11)0.0194 (11)
C210.0472 (15)0.0697 (18)0.0418 (14)0.0068 (13)0.0009 (12)0.0117 (13)
C220.0358 (12)0.0418 (13)0.0403 (13)0.0016 (10)0.0091 (10)0.0155 (10)
C230.0496 (15)0.0527 (15)0.0443 (14)0.0070 (12)0.0071 (11)0.0182 (12)
C240.0499 (15)0.0545 (16)0.0604 (17)0.0119 (13)0.0051 (13)0.0171 (14)
C250.0599 (18)0.0586 (17)0.0645 (19)0.0155 (14)0.0222 (15)0.0116 (14)
C260.078 (2)0.0679 (18)0.0436 (15)0.0134 (16)0.0225 (14)0.0161 (14)
C270.0542 (15)0.0537 (15)0.0435 (14)0.0059 (12)0.0101 (12)0.0180 (12)
O10.0375 (8)0.0448 (9)0.0449 (9)0.0048 (7)0.0126 (7)0.0197 (7)
O20.0509 (10)0.0578 (11)0.0424 (9)0.0043 (8)0.0170 (8)0.0208 (8)
O30.0800 (13)0.0536 (11)0.0486 (10)0.0135 (10)0.0324 (10)0.0132 (9)
O40.0520 (11)0.0981 (15)0.0407 (10)0.0174 (10)0.0081 (9)0.0240 (10)
O50.0387 (9)0.0698 (11)0.0414 (9)0.0078 (8)0.0072 (7)0.0126 (8)
O60.0572 (11)0.0820 (13)0.0399 (10)0.0084 (10)0.0027 (8)0.0121 (10)
C280.0563 (17)0.0654 (19)0.0576 (17)0.0163 (14)0.0223 (14)0.0208 (15)
C290.086 (2)0.0555 (17)0.074 (2)0.0036 (16)0.0292 (18)0.0263 (16)
C300.0672 (19)0.0603 (18)0.0648 (19)0.0095 (15)0.0181 (16)0.0067 (15)
C310.0571 (17)0.0624 (18)0.0564 (17)0.0122 (14)0.0182 (14)0.0187 (15)
C320.077 (2)0.0544 (17)0.070 (2)0.0091 (15)0.0203 (17)0.0258 (15)
C330.0623 (18)0.0573 (18)0.0628 (18)0.0003 (14)0.0153 (15)0.0113 (15)
C340.089 (2)0.110 (3)0.069 (2)0.024 (2)0.0163 (18)0.0382 (19)
C350.088 (2)0.109 (3)0.066 (2)0.019 (2)0.0071 (18)0.031 (2)
Geometric parameters (Å, º) top
Br1—C81.893 (2)C17—H170.9300
C1—O11.431 (3)C18—C191.392 (3)
C1—C51.503 (3)C18—H180.9300
C1—C21.585 (3)C20—O41.191 (3)
C1—H10.9800C20—O51.319 (3)
C2—C131.512 (3)C21—O51.450 (3)
C2—C31.533 (3)C21—H21A0.9600
C2—C111.562 (3)C21—H21B0.9600
C3—C191.499 (3)C21—H21C0.9600
C3—C41.549 (3)C22—C271.378 (3)
C3—H30.9800C22—C231.389 (3)
C4—O11.434 (3)C23—C241.380 (3)
C4—C221.519 (3)C23—H230.9300
C4—C201.541 (3)C24—C251.370 (4)
C5—C61.374 (3)C24—H240.9300
C5—C101.394 (3)C25—C261.373 (4)
C6—C71.386 (3)C25—H250.9300
C6—H60.9300C26—C271.376 (3)
C7—C81.371 (4)C26—H260.9300
C7—H70.9300C27—H270.9300
C8—C91.373 (4)C28—C331.371 (4)
C9—C101.375 (3)C28—C291.381 (4)
C9—H90.9300C28—C341.507 (4)
C10—H100.9300C29—C301.380 (4)
C11—O61.195 (3)C29—H290.9300
C11—C121.485 (3)C30—C311.376 (4)
C12—H12A0.9600C30—H300.9300
C12—H12B0.9600C31—C321.366 (4)
C12—H12C0.9600C31—C351.510 (4)
C13—O31.197 (3)C32—C331.382 (4)
C13—O21.351 (3)C32—H320.9300
C14—C191.382 (3)C33—H330.9300
C14—C151.382 (3)C34—H34A0.9600
C14—O21.393 (3)C34—H34B0.9600
C15—C161.374 (4)C34—H34C0.9600
C15—H150.9300C35—H35A0.9600
C16—C171.377 (4)C35—H35B0.9600
C16—H160.9300C35—H35C0.9600
C17—C181.378 (4)
O1—C1—C5109.91 (17)C17—C18—C19121.3 (2)
O1—C1—C2105.05 (16)C17—C18—H18119.4
C5—C1—C2116.77 (18)C19—C18—H18119.4
O1—C1—H1108.3C14—C19—C18116.9 (2)
C5—C1—H1108.3C14—C19—C3120.6 (2)
C2—C1—H1108.3C18—C19—C3122.4 (2)
C13—C2—C3113.81 (18)O4—C20—O5123.8 (2)
C13—C2—C11110.52 (18)O4—C20—C4123.8 (2)
C3—C2—C11109.85 (17)O5—C20—C4112.20 (19)
C13—C2—C1108.75 (18)O5—C21—H21A109.5
C3—C2—C1102.97 (17)O5—C21—H21B109.5
C11—C2—C1110.69 (17)H21A—C21—H21B109.5
C19—C3—C2113.69 (18)O5—C21—H21C109.5
C19—C3—C4119.85 (18)H21A—C21—H21C109.5
C2—C3—C4104.27 (17)H21B—C21—H21C109.5
C19—C3—H3106.0C27—C22—C23118.5 (2)
C2—C3—H3106.0C27—C22—C4119.2 (2)
C4—C3—H3106.0C23—C22—C4122.2 (2)
O1—C4—C22108.68 (16)C24—C23—C22120.6 (2)
O1—C4—C20107.09 (16)C24—C23—H23119.7
C22—C4—C20113.98 (18)C22—C23—H23119.7
O1—C4—C3101.66 (16)C25—C24—C23120.1 (3)
C22—C4—C3112.61 (17)C25—C24—H24120.0
C20—C4—C3111.87 (18)C23—C24—H24120.0
C6—C5—C10118.6 (2)C24—C25—C26119.6 (2)
C6—C5—C1123.1 (2)C24—C25—H25120.2
C10—C5—C1118.3 (2)C26—C25—H25120.2
C5—C6—C7120.8 (2)C25—C26—C27120.6 (2)
C5—C6—H6119.6C25—C26—H26119.7
C7—C6—H6119.6C27—C26—H26119.7
C8—C7—C6119.4 (2)C26—C27—C22120.5 (2)
C8—C7—H7120.3C26—C27—H27119.7
C6—C7—H7120.3C22—C27—H27119.7
C7—C8—C9120.9 (2)C1—O1—C4107.63 (15)
C7—C8—Br1119.9 (2)C13—O2—C14122.04 (18)
C9—C8—Br1119.17 (19)C20—O5—C21116.96 (19)
C8—C9—C10119.4 (2)C33—C28—C29117.1 (3)
C8—C9—H9120.3C33—C28—C34122.1 (3)
C10—C9—H9120.3C29—C28—C34120.8 (3)
C9—C10—C5120.9 (2)C30—C29—C28120.8 (3)
C9—C10—H10119.6C30—C29—H29119.6
C5—C10—H10119.6C28—C29—H29119.6
O6—C11—C12122.2 (2)C31—C30—C29121.9 (3)
O6—C11—C2118.4 (2)C31—C30—H30119.0
C12—C11—C2119.3 (2)C29—C30—H30119.0
C11—C12—H12A109.5C32—C31—C30117.0 (3)
C11—C12—H12B109.5C32—C31—C35121.2 (3)
H12A—C12—H12B109.5C30—C31—C35121.8 (3)
C11—C12—H12C109.5C31—C32—C33121.5 (3)
H12A—C12—H12C109.5C31—C32—H32119.2
H12B—C12—H12C109.5C33—C32—H32119.2
O3—C13—O2118.0 (2)C28—C33—C32121.7 (3)
O3—C13—C2123.4 (2)C28—C33—H33119.2
O2—C13—C2118.4 (2)C32—C33—H33119.2
C19—C14—C15122.6 (2)C28—C34—H34A109.5
C19—C14—O2122.1 (2)C28—C34—H34B109.5
C15—C14—O2115.3 (2)H34A—C34—H34B109.5
C16—C15—C14119.1 (2)C28—C34—H34C109.5
C16—C15—H15120.4H34A—C34—H34C109.5
C14—C15—H15120.4H34B—C34—H34C109.5
C15—C16—C17119.9 (2)C31—C35—H35A109.5
C15—C16—H16120.1C31—C35—H35B109.5
C17—C16—H16120.1H35A—C35—H35B109.5
C16—C17—C18120.3 (3)C31—C35—H35C109.5
C16—C17—H17119.9H35A—C35—H35C109.5
C18—C17—H17119.9H35B—C35—H35C109.5
O1—C1—C2—C13129.95 (18)O2—C14—C19—C18179.9 (2)
C5—C1—C2—C13108.0 (2)C15—C14—C19—C3178.5 (2)
O1—C1—C2—C38.9 (2)O2—C14—C19—C33.2 (3)
C5—C1—C2—C3130.94 (19)C17—C18—C19—C142.0 (4)
O1—C1—C2—C11108.46 (19)C17—C18—C19—C3178.8 (2)
C5—C1—C2—C1113.6 (3)C2—C3—C19—C1413.8 (3)
C13—C2—C3—C1931.3 (3)C4—C3—C19—C14110.4 (2)
C11—C2—C3—C1993.3 (2)C2—C3—C19—C18163.0 (2)
C1—C2—C3—C19148.80 (17)C4—C3—C19—C1872.8 (3)
C13—C2—C3—C4101.0 (2)O1—C4—C20—O4104.8 (3)
C11—C2—C3—C4134.49 (18)C22—C4—C20—O4135.0 (2)
C1—C2—C3—C416.5 (2)C3—C4—C20—O45.8 (3)
C19—C3—C4—O1165.07 (17)O1—C4—C20—O569.5 (2)
C2—C3—C4—O136.46 (19)C22—C4—C20—O550.7 (3)
C19—C3—C4—C2278.8 (2)C3—C4—C20—O5179.93 (18)
C2—C3—C4—C22152.58 (17)O1—C4—C22—C2739.0 (3)
C19—C3—C4—C2051.1 (3)C20—C4—C22—C27158.4 (2)
C2—C3—C4—C2077.5 (2)C3—C4—C22—C2772.8 (3)
O1—C1—C5—C624.6 (3)O1—C4—C22—C23144.0 (2)
C2—C1—C5—C694.9 (3)C20—C4—C22—C2324.7 (3)
O1—C1—C5—C10156.77 (19)C3—C4—C22—C23104.1 (2)
C2—C1—C5—C1083.8 (2)C27—C22—C23—C241.2 (4)
C10—C5—C6—C70.9 (4)C4—C22—C23—C24178.2 (2)
C1—C5—C6—C7177.8 (2)C22—C23—C24—C250.4 (4)
C5—C6—C7—C80.4 (4)C23—C24—C25—C261.7 (4)
C6—C7—C8—C91.1 (4)C24—C25—C26—C271.4 (4)
C6—C7—C8—Br1177.64 (19)C25—C26—C27—C220.2 (4)
C7—C8—C9—C100.6 (4)C23—C22—C27—C261.5 (4)
Br1—C8—C9—C10178.21 (19)C4—C22—C27—C26178.5 (2)
C8—C9—C10—C50.7 (4)C5—C1—O1—C4160.22 (17)
C6—C5—C10—C91.4 (4)C2—C1—O1—C433.8 (2)
C1—C5—C10—C9177.3 (2)C22—C4—O1—C1163.18 (16)
C13—C2—C11—O6158.5 (2)C20—C4—O1—C173.3 (2)
C3—C2—C11—O632.1 (3)C3—C4—O1—C144.22 (19)
C1—C2—C11—O680.9 (3)O3—C13—O2—C14165.6 (2)
C13—C2—C11—C1223.4 (3)C2—C13—O2—C1419.3 (3)
C3—C2—C11—C12149.8 (2)C19—C14—O2—C130.8 (3)
C1—C2—C11—C1297.2 (2)C15—C14—O2—C13179.2 (2)
C3—C2—C13—O3150.0 (2)O4—C20—O5—C213.2 (3)
C11—C2—C13—O385.9 (3)C4—C20—O5—C21177.52 (19)
C1—C2—C13—O335.8 (3)C33—C28—C29—C301.3 (4)
C3—C2—C13—O235.2 (3)C34—C28—C29—C30177.0 (3)
C11—C2—C13—O289.0 (2)C28—C29—C30—C310.8 (5)
C1—C2—C13—O2149.32 (19)C29—C30—C31—C320.1 (4)
C19—C14—C15—C160.2 (4)C29—C30—C31—C35179.6 (3)
O2—C14—C15—C16178.6 (2)C30—C31—C32—C330.3 (4)
C14—C15—C16—C170.9 (4)C35—C31—C32—C33179.4 (3)
C15—C16—C17—C180.6 (4)C29—C28—C33—C321.1 (4)
C16—C17—C18—C190.9 (4)C34—C28—C33—C32177.2 (3)
C15—C14—C19—C181.6 (3)C31—C32—C33—C280.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O30.982.452.829 (3)103
C3—H3···O60.982.232.765 (3)113
C6—H6···O6i0.932.573.289 (3)135
C12—H12C···O5ii0.962.673.595 (3)162
C21—H21C···O4iii0.962.733.660 (4)163
C25—H25···Br1iv0.933.334.047 (3)135
C35—H35B···O3v0.962.833.523 (4)129
C24—H24···Cg1v0.932.943.579 (3)127
C35—H35C···Cg2vi0.962.953.764 (4)143
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1, y, z; (iii) x+1, y+1, z+2; (iv) x1, y+1, z; (v) x1, y, z; (vi) x+1, y, z+2.
Isostructurality indices calculated for solvates (Ia)–(Ic) top
SolvatesΠAIv(max) (%)
(Ia)–(Ib)0.0041.1698.3
(Ia)–(Ic)0.0170.9796.8
(Ib)–(Ic)0.0131.3498.6
Π is the unit-cell similarity descriptor, A is the aspericity index and Iv is the volumetric isostructurality index.
 

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