Last of the gem-Difluorocycloalkanes: Synthesis and Characterization of 2,2-Difluorocyclobutyl-Substituted Building Blocks.
Chernykh, Anton V.; Melnykov, Kostiantyn P.; Tolmacheva, Nataliya A.; Kondratov, Ivan S.; Radchenko, Dmytro S.; Daniliuc, Constantin G.; Volochnyuk, Dmitriy M.; Ryabukhin, Sergey V.; Kuchkovska, Yuliya O.; Grygorenko, Oleksandr O.; The Journal of organic chemistry 84 (2019) 8487–8496; doi:10.1021/acs.joc.9b00719

data_4033602
_publ_section_title
;
 Last of the gem-Difluorocycloalkanes: Synthesis and Characterization of
 2,2-Difluorocyclobutyl-Substituted Building Blocks.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8487
_journal_page_last               8496
_journal_paper_doi               10.1021/acs.joc.9b00719
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C4 H8 F2 N, Cl'
_chemical_formula_sum            'C4 H8 Cl F2 N'
_chemical_formula_weight         143.56
_space_group_crystal_system      orthorhombic
_space_group_IT_number           31
_space_group_name_Hall           'P 2ac -2'
_space_group_name_H-M_alt        'P m n 21'
_symmetry_space_group_name_Hall  'P 2ac -2'
_symmetry_space_group_name_H-M   'P m n 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0161(13)
_cell_length_b                   7.0221(17)
_cell_length_c                   7.620(2)
_cell_measurement_reflns_used    595
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.11
_cell_measurement_theta_min      2.90
_cell_volume                     321.91(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4053
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.591
_diffrn_reflns_theta_min         2.901
_exptl_absorpt_coefficient_mu    0.529
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.73
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_description       block
_exptl_crystal_F_000             148
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.45(10)
_refine_ls_extinction_coef       0.119(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         731
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0244
_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^)+(0.0396P)^2^+0.0381P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0598
_refine_ls_wR_factor_ref         0.0605
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                705
_reflns_number_total             731
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00719_si_003.cif
_cod_data_source_block           xr130
_cod_depositor_comments
'Adding full bibliography for 4033602--4033603.cif.'
_cod_database_code               4033602
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_min   0.832
_shelx_estimated_absorpt_t_max   0.939
_shelx_res_checksum              55348
_shelx_hkl_checksum              3563