Difluorination of Furonaphthoquinones.
Li, Jie; Xue, Yu; Fan, Zhoulong; Ding, Chunyong; Zhang, Ao; The Journal of organic chemistry 82 (2017) 7388–7393; doi:10.1021/acs.joc.7b01064

data_4032617
_publ_section_title
;
 Difluorination of Furonaphthoquinones.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7388
_journal_page_last               7393
_journal_paper_doi               10.1021/acs.joc.7b01064
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C19 H16 F3 O3'
_chemical_formula_sum            'C19 H16 F3 O3'
_chemical_formula_weight         349.32
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-06
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.9870(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3744(2)
_cell_length_b                   17.1213(4)
_cell_length_c                   7.8002(2)
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    173.1
_cell_measurement_theta_max      68.206
_cell_measurement_theta_min      4.444
_cell_volume                     1632.31(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.01
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            19755
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.274
_diffrn_reflns_theta_min         4.445
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.011
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0859 before and 0.0405 after correction. The Ratio of minimum to maximum transmission is 0.9016. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       block
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         2985
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0920P)^2^+1.1910P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1492
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2776
_reflns_number_total             2985
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01064_si_002.cif
_cod_data_source_block           ta_a_cmpd_7u
_cod_depositor_comments
'Adding full bibliography for 4032614--4032617.cif.'
_cod_database_code               4032617
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C21-C4 \\sim C3-C4
 with sigma of 0.02
 C21-C2 \\sim C20-C3
 with sigma of 0.02
 C20-C1 \\sim C2-C1 \\sim C20-C21 \\sim C2-C3 \\sim C21-C4 \\sim C3-C4
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C3) \\sim Ueq, Uanis(C21) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
4. Others
 Fixed Sof: H4B(0.7) H4A(0.3) C3(0.7) H3(0.7) C2(0.7) H2A(0.7) C20(0.3)
 H20(0.3) C21(0.3) H21(0.3)
5.a Ternary CH refined with riding coordinates:
 C15(H15)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4B), C4(H4A), C8(H8), C7(H7), C3(H3), C2(H2A), C20(H20), C21(H21)
5.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C)
5.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'