Borinic Acid Catalyzed, Regioselective Chloroacylations and Chlorosulfonylations of 2,3-Epoxy Alcohols.
Tanveer, Kashif; Jarrah, Kareem; Taylor, Mark S.; Organic letters 17 (2015) 3482–3485; doi:10.1021/acs.orglett.5b01541

data_1520684
_publ_section_title
;
 Borinic Acid Catalyzed, Regioselective Chloroacylations and
 Chlorosulfonylations of 2,3-Epoxy Alcohols.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3482
_journal_page_last               3485
_journal_paper_doi               10.1021/acs.orglett.5b01541
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H17 Cl O3'
_chemical_formula_sum            'C13 H17 Cl O3'
_chemical_formula_weight         256.71
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   mixed
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   28.508(2)
_cell_length_b                   5.4891(4)
_cell_length_c                   8.1976(7)
_cell_measurement_reflns_used    1737
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      23.06
_cell_measurement_theta_min      2.87
_cell_volume                     1282.79(17)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2008)'
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_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8900
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.632
_diffrn_reflns_theta_min         2.858
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
; 
 Flack x determined using 914 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.12(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2931
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0338P)^2^+0.1798P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0885
_reflns_Friedel_coverage         0.842
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                2455
_reflns_number_total             2931
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01541_si_001.cif
_cod_data_source_block           Tanveer-3a
_cod_depositor_comments
'Adding full bibliography for 1520684--1520685.cif.'
_cod_original_cell_volume        1282.79(18)
_cod_database_code               1520684
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.902
_shelx_estimated_absorpt_t_max   0.977
_shelx_res_checksum              46708
_shelx_hkl_checksum              92577