Homologation Strategy for the Generation of 1-Chloroalkyl Radicals from Organoboranes.
Xu, Gong; Lüthy, Monique; Habegger, Jacqueline; Renaud, Philippe; The Journal of organic chemistry 81 (2016) 1506–1519; doi:10.1021/acs.joc.5b02610

data_4031858
_publ_section_title
;
 Homologation Strategy for the Generation of 1-Chloroalkyl Radicals from
 Organoboranes.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1506
_journal_page_last               1519
_journal_paper_doi               10.1021/acs.joc.5b02610
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H13 Cl O2'
_chemical_formula_weight         236.68
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-12-11T11:40:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
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_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.14393(11)
_cell_length_b                   8.45999(13)
_cell_length_c                   16.9460(2)
_cell_measurement_reflns_used    5625
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.249
_cell_measurement_theta_min      2.3989
_cell_volume                     1167.54(3)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
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        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 16.0965
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.015214
_diffrn_orient_matrix_UB_12      0.0324098
_diffrn_orient_matrix_UB_13      -0.0378966
_diffrn_orient_matrix_UB_21      0.0306438
_diffrn_orient_matrix_UB_22      -0.0699683
_diffrn_orient_matrix_UB_23      -0.0177457
_diffrn_orient_matrix_UB_31      -0.0800965
_diffrn_orient_matrix_UB_32      -0.0329562
_diffrn_orient_matrix_UB_33      0.000409
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9021
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         27.31
_diffrn_reflns_theta_min         2.4
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  1.414
_exptl_absorpt_correction_T_min  1.066
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_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
        (compiled Jul 11 2012,15:38:31)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
;
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.3497
_exptl_crystal_size_mid          0.2963
_exptl_crystal_size_min          0.1686
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2389
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0238P)^2^+0.1304P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0584
_refine_ls_wR_factor_ref         0.0602
_reflns_number_gt                2242
_reflns_number_total             2389
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02610_si_004.cif
_cod_data_source_block           12pr002
_cod_depositor_comments
'Adding full bibliography for 4031857--4031859.cif.'
_cod_database_code               4031858