Stereospecific Halogenation of P(O)-H Bonds with Copper(II) Chloride Affording Optically Active Z1Z2P(O)Cl
Yongbo Zhou; Gang Wang; Yuta Saga; Ruwei Shen; Midori Goto; Yufen Zhao; Li-Biao Han; Journal of Organic Chemistry 75 (2010) 7924–7927; doi:10.1021/jo101540d

data_4025820
_publ_section_title
;
 Stereospecific Halogenation of P(O)-H Bonds with Copper(II) Chloride
 Affording Optically Active Z1Z2P(O)Cl
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7924
_journal_page_last               7927
_journal_paper_doi               10.1021/jo101540d
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C10 H14 Cl O P'
_chemical_formula_weight         216.63
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9362(4)
_cell_length_b                   12.0141(6)
_cell_length_c                   12.0610(6)
_cell_measurement_reflns_used    9187
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.071
_cell_measurement_theta_min      2.393
_cell_volume                     1149.97(10)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating unit'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0140
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13252
_diffrn_reflns_theta_full        26.22
_diffrn_reflns_theta_max         28.22
_diffrn_reflns_theta_min         2.39
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  1020
_diffrn_standards_number         169
_exptl_absorpt_coefficient_mu    0.433
_exptl_absorpt_correction_T_max  0.9787
_exptl_absorpt_correction_T_min  0.8995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.868
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         2679
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.868
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0251
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0869P)^2^+0.3420P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0744
_refine_ls_wR_factor_ref         0.0765
_reflns_number_gt                2587
_reflns_number_total             2679
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101540d_si_001.cif
_cod_data_source_block           han6a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to the built-in table from CIF Core
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025820