# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_FUR-A
_audit_block_doi                 10.5517/ccdc.csd.cc21hcpm
_database_code_depnum_ccdc_archive 'CCDC 1891610'
loop_
_audit_author_name
_audit_author_address
'Deborah de Alencar Simoni'
;University of Campinas
Brazil
;
#Added by publCIF



_audit_update_record             
;
2019-01-17 deposited with the CCDC.	2020-04-08 downloaded from the CCDC.
;
#Added by publCIF


_publcif_datablock.id            {d9bb4aa3-109e-40ba-bc30-91ae974a3651}
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
(4Z)-2,4-diphenyl-8,9-dihydrocycloocta[b]furan-6(7H)-one

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 O2'
_chemical_formula_sum            'C22 H18 O2'
_chemical_formula_weight         314.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.6541(5)
_cell_length_b                   5.7809(3)
_cell_length_c                   33.543(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.281(4)
_cell_angle_gamma                90
_cell_volume                     1664.55(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    92
_cell_measurement_theta_min      9.28
_cell_measurement_theta_max      36.79

_exptl_crystal_description       PLATE
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.032
_exptl_absorpt_coefficient_mu    0.624
_shelx_estimated_absorpt_T_min   0.866
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6111
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'

_exptl_special_details           ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            6055
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_av_R_equivalents  0.0604
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         5.152
_diffrn_reflns_theta_max         68.820
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.837
_diffrn_measured_fraction_theta_full 0.854
_diffrn_reflns_Laue_measured_fraction_max 0.837
_diffrn_reflns_Laue_measured_fraction_full 0.854
_diffrn_reflns_point_group_measured_fraction_max 0.837
_diffrn_reflns_point_group_measured_fraction_full 0.854
_reflns_number_total             2583
_reflns_number_gt                2018
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+1.1175P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2583
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1326
_refine_ls_wR_factor_gt          0.1262
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_restrained_S_all      1.130
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.69565(19) 0.6404(3) 0.35811(5) 0.0329(4) Uani 1 1 d . . . . .
O2 O 0.6417(2) 0.2678(4) 0.51480(5) 0.0444(5) Uani 1 1 d . . . . .
C1 C 0.7782(3) 0.6827(5) 0.27835(8) 0.0386(6) Uani 1 1 d . . . . .
H1 H 0.8055 0.8052 0.2968 0.046 Uiso 1 1 calc R U . . .
C2 C 0.8294(3) 0.6878(5) 0.24099(8) 0.0420(7) Uani 1 1 d . . . . .
H2 H 0.8906 0.8139 0.2338 0.050 Uiso 1 1 calc R U . . .
C3 C 0.7914(3) 0.5082(5) 0.21387(8) 0.0416(7) Uani 1 1 d . . . . .
H3 H 0.8280 0.5098 0.1883 0.050 Uiso 1 1 calc R U . . .
C4 C 0.7001(3) 0.3279(6) 0.22433(8) 0.0438(7) Uani 1 1 d . . . . .
H4 H 0.6722 0.2069 0.2056 0.053 Uiso 1 1 calc R U . . .
C5 C 0.6488(3) 0.3208(5) 0.26162(8) 0.0383(6) Uani 1 1 d . . . . .
H5 H 0.5874 0.1944 0.2686 0.046 Uiso 1 1 calc R U . . .
C6 C 0.6873(3) 0.5005(5) 0.28936(7) 0.0327(6) Uani 1 1 d . . . . .
C7 C 0.6329(3) 0.4844(5) 0.32881(7) 0.0320(6) Uani 1 1 d . . . . .
C8 C 0.5336(3) 0.3429(5) 0.34451(7) 0.0321(6) Uani 1 1 d . . . . .
H8 H 0.4739 0.2232 0.3306 0.039 Uiso 1 1 calc R U . . .
C9 C 0.5336(3) 0.4041(4) 0.38600(7) 0.0303(5) Uani 1 1 d . . . . .
C10 C 0.6338(3) 0.5865(5) 0.39243(7) 0.0323(6) Uani 1 1 d . . . . .
C11 C 0.6874(3) 0.7187(5) 0.42978(7) 0.0385(6) Uani 1 1 d . . . . .
H11A H 0.5983 0.7427 0.4451 0.046 Uiso 1 1 calc R U . . .
H11B H 0.7253 0.8726 0.4225 0.046 Uiso 1 1 calc R U . . .
C12 C 0.8186(3) 0.5914(5) 0.45646(8) 0.0426(7) Uani 1 1 d . . . . .
H12A H 0.9173 0.6106 0.4448 0.051 Uiso 1 1 calc R U . . .
H12B H 0.8323 0.6629 0.4835 0.051 Uiso 1 1 calc R U . . .
C13 C 0.7854(3) 0.3340(5) 0.46057(8) 0.0392(6) Uani 1 1 d . . . . .
H13A H 0.7783 0.2609 0.4337 0.047 Uiso 1 1 calc R U . . .
H13B H 0.8736 0.2616 0.4778 0.047 Uiso 1 1 calc R U . . .
C14 C 0.6363(3) 0.2869(4) 0.47844(7) 0.0339(6) Uani 1 1 d . . . . .
C15 C 0.4842(3) 0.2587(4) 0.45374(7) 0.0336(6) Uani 1 1 d . . . . .
H15 H 0.4039 0.2017 0.4679 0.040 Uiso 1 1 calc R U . . .
C16 C 0.4394(3) 0.3001(4) 0.41433(7) 0.0307(5) Uani 1 1 d . . . . .
C17 C 0.2742(3) 0.2475(5) 0.39742(7) 0.0309(5) Uani 1 1 d . . . . .
C18 C 0.1909(3) 0.4098(5) 0.37253(7) 0.0354(6) Uani 1 1 d . . . . .
H18 H 0.2397 0.5493 0.3659 0.043 Uiso 1 1 calc R U . . .
C19 C 0.0368(3) 0.3676(5) 0.35744(8) 0.0402(6) Uani 1 1 d . . . . .
H19 H -0.0201 0.4799 0.3409 0.048 Uiso 1 1 calc R U . . .
C20 C -0.0347(3) 0.1636(5) 0.36629(8) 0.0392(6) Uani 1 1 d . . . . .
H20 H -0.1403 0.1357 0.3559 0.047 Uiso 1 1 calc R U . . .
C21 C 0.0485(3) 0.0000(5) 0.39037(8) 0.0393(6) Uani 1 1 d . . . . .
H21 H 0.0005 -0.1420 0.3960 0.047 Uiso 1 1 calc R U . . .
C22 C 0.2022(3) 0.0430(5) 0.40627(7) 0.0354(6) Uani 1 1 d . . . . .
H22 H 0.2580 -0.0682 0.4233 0.043 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 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.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.365(3) . ?
O1 C7 1.393(3) . ?
O2 C14 1.220(3) . ?
C1 C2 1.381(4) . ?
C1 C6 1.392(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.392(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.406(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.463(4) . ?
C7 C8 1.341(4) . ?
C8 C9 1.436(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.365(4) . ?
C9 C16 1.458(4) . ?
C10 C11 1.490(4) . ?
C11 C12 1.541(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.525(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.515(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.472(3) . ?
C15 C16 1.351(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.500(3) . ?
C17 C22 1.386(4) . ?
C17 C18 1.395(3) . ?
C18 C19 1.386(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.385(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 C7 106.73(19) . . ?
C2 C1 C6 120.9(3) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C1 C2 C3 120.0(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.5(2) . . ?
C1 C6 C7 123.1(2) . . ?
C5 C6 C7 118.4(2) . . ?
C8 C7 O1 109.2(2) . . ?
C8 C7 C6 133.6(2) . . ?
O1 C7 C6 117.1(2) . . ?
C7 C8 C9 108.0(2) . . ?
C7 C8 H8 126.0 . . ?
C9 C8 H8 126.0 . . ?
C10 C9 C8 105.4(2) . . ?
C10 C9 C16 127.8(2) . . ?
C8 C9 C16 126.8(2) . . ?
C9 C10 O1 110.6(2) . . ?
C9 C10 C11 130.7(2) . . ?
O1 C10 C11 118.6(2) . . ?
C10 C11 C12 111.8(2) . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 112.7(2) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C14 C13 C12 113.0(2) . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
O2 C14 C15 118.1(2) . . ?
O2 C14 C13 119.0(2) . . ?
C15 C14 C13 122.9(2) . . ?
C16 C15 C14 131.0(2) . . ?
C16 C15 H15 114.5 . . ?
C14 C15 H15 114.5 . . ?
C15 C16 C9 126.6(2) . . ?
C15 C16 C17 118.4(2) . . ?
C9 C16 C17 114.9(2) . . ?
C22 C17 C18 119.3(2) . . ?
C22 C17 C16 121.6(2) . . ?
C18 C17 C16 119.1(2) . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 120.5(3) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 119.6(2) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C20 C21 C22 120.2(3) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 120.3(2) . . ?
C17 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.6(4) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
C2 C3 C4 C5 -1.4(4) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
C2 C1 C6 C7 178.7(2) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
C4 C5 C6 C7 -178.9(2) . . . . ?
C10 O1 C7 C8 1.2(3) . . . . ?
C10 O1 C7 C6 -177.3(2) . . . . ?
C1 C6 C7 C8 171.9(3) . . . . ?
C5 C6 C7 C8 -9.6(4) . . . . ?
C1 C6 C7 O1 -10.0(4) . . . . ?
C5 C6 C7 O1 168.5(2) . . . . ?
O1 C7 C8 C9 -1.4(3) . . . . ?
C6 C7 C8 C9 176.8(3) . . . . ?
C7 C8 C9 C10 1.1(3) . . . . ?
C7 C8 C9 C16 178.1(2) . . . . ?
C8 C9 C10 O1 -0.3(3) . . . . ?
C16 C9 C10 O1 -177.3(2) . . . . ?
C8 C9 C10 C11 -177.2(3) . . . . ?
C16 C9 C10 C11 5.8(4) . . . . ?
C7 O1 C10 C9 -0.5(3) . . . . ?
C7 O1 C10 C11 176.8(2) . . . . ?
C9 C10 C11 C12 80.8(3) . . . . ?
O1 C10 C11 C12 -95.8(3) . . . . ?
C10 C11 C12 C13 -44.7(3) . . . . ?
C11 C12 C13 C14 -59.1(3) . . . . ?
C12 C13 C14 O2 -90.4(3) . . . . ?
C12 C13 C14 C15 90.7(3) . . . . ?
O2 C14 C15 C16 169.9(3) . . . . ?
C13 C14 C15 C16 -11.2(4) . . . . ?
C14 C15 C16 C9 -5.1(5) . . . . ?
C14 C15 C16 C17 178.4(3) . . . . ?
C10 C9 C16 C15 -40.8(4) . . . . ?
C8 C9 C16 C15 142.8(3) . . . . ?
C10 C9 C16 C17 135.8(3) . . . . ?
C8 C9 C16 C17 -40.6(4) . . . . ?
C15 C16 C17 C22 -45.0(3) . . . . ?
C9 C16 C17 C22 138.0(2) . . . . ?
C15 C16 C17 C18 134.2(3) . . . . ?
C9 C16 C17 C18 -42.7(3) . . . . ?
C22 C17 C18 C19 1.1(4) . . . . ?
C16 C17 C18 C19 -178.2(2) . . . . ?
C17 C18 C19 C20 -1.1(4) . . . . ?
C18 C19 C20 C21 -0.1(4) . . . . ?
C19 C20 C21 C22 1.4(4) . . . . ?
C18 C17 C22 C21 0.2(4) . . . . ?
C16 C17 C22 C21 179.5(2) . . . . ?
C20 C21 C22 C17 -1.4(4) . . . . ?

_refine_diff_density_max         0.151
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.038

_shelxl_version_number           2014-3


# start Validation Reply Form

_vrf_PLAT029_FUR-A               
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low . 0.854 Why?
RESPONSE: it was too difficult to obtain suitable crystals of
(4Z)-2,4-diphenyl-8,9-dihydrocycloocta[b]furan-6(7H)-one and the ones that
 had been formed presented severe  limitation to diffract X-ray radiation,  
 even after a number of recrystallizations of the compound.                  
 The data collection strategy as well as the data reduction                 
 were optimized to favour completeness, but these
 efforts were not enough to overcome this problem.                         
 It is important to mention that the structure refinement converged and the
 proposed structure is corroborated by the results of other analysis.
;
_vrf_PLAT911_FUR-A               
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L= 0.600 437 Report
RESPONSE: same explanation as for PLAT029_ALERT_3_A
 
;

loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone and water'
