Synthesis of Vicinal Dichlorides via Activation of Aliphatic Terminal Epoxides with Triphosgene and Pyridine.
Cleveland, Alexander H.; Fronczek, Frank R.; Kartika, Rendy; The Journal of organic chemistry 83 (2018) 3367–3377; doi:10.1021/acs.joc.7b03197

data_4033526
_publ_section_title
;
 Synthesis of Vicinal Dichlorides via Activation of Aliphatic Terminal
 Epoxides with Triphosgene and Pyridine.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3367
_journal_page_last               3377
_journal_paper_doi               10.1021/acs.joc.7b03197
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C10 H8 N2 O7'
_chemical_formula_sum            'C10 H8 N2 O7'
_chemical_formula_weight         268.18
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3640(2)
_cell_length_b                   10.4478(3)
_cell_length_c                   19.1395(6)
_cell_measurement_reflns_used    9671
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      69.33
_cell_measurement_theta_min      4.62
_cell_volume                     1072.62(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(5)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'QUAZAR multilayer optics'
_diffrn_radiation_source         'I\mS microfocus'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10328
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         69.325
_diffrn_reflns_theta_min         4.621
_exptl_absorpt_coefficient_mu    1.260
_exptl_absorpt_correction_T_max  0.805
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_description       'needle fragment'
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 785 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         1989
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0224
_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^)+(0.0355P)^2^+0.1707P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0582
_refine_ls_wR_factor_ref         0.0584
_reflns_Friedel_coverage         0.658
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                1981
_reflns_number_total             1989
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b03197_si_002.cif
_cod_data_source_block           Cleveland1
_cod_depositor_comments          'Adding full bibliography for 4033526.cif.'
_cod_database_code               4033526
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.704
_shelx_estimated_absorpt_t_max   0.805
_shelx_res_checksum              23001
_shelx_hkl_checksum              24341