Synthesis of gem-Difluoromethylenated Polycyclic Cage Compounds.
Masusai, Chonticha; Soorukram, Darunee; Kuhakarn, Chutima; Tuchinda, Patoomratana; Pakawatchai, Chaveng; Saithong, Saowanit; Reutrakul, Vichai; Pohmakotr, Manat; The Journal of organic chemistry 80 (2015) 1577–1592; doi:10.1021/jo502501v

data_4030585
_publ_section_title
;
 Synthesis of gem-Difluoromethylenated Polycyclic Cage Compounds.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1577
_journal_page_last               1592
_journal_paper_doi               10.1021/jo502501v
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C16  H14  O3  F2  S1'
_chemical_formula_sum            'C16 H14 F2 O3 S'
_chemical_formula_weight         324.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90.379(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6313(10)
_cell_length_b                   10.6643(17)
_cell_length_c                   21.166(3)
_cell_measurement_reflns_used    16753
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      41.362
_cell_measurement_theta_min      5.408
_cell_volume                     1496.8(4)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'Mercury 2.3 (Macrea <i>et al</i>., 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'Frames, each covering 0.3 \% in \w'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1199
_diffrn_reflns_av_unetI/netI     0.0897
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11968
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.138
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.116
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       2.33(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2541
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0738
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0787P)^2^+0.1408P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1598
_refine_ls_wR_factor_ref         0.1699
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2047
_reflns_number_total             2541
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo502501v_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 4030584--4030587.cif.'
_cod_database_code               4030585
_shelxl_version_number           2013-4
_shelx_res_checksum              53880
_shelx_hkl_checksum              86569