Direct Conversion of Alcohols to α-Chloro Aldehydes and α-Chloro Ketones.
Jing, Yuanyuan; Daniliuc, Constantin G.; Studer, Armido; Organic letters 16 (2014) 4932–4935; doi:10.1021/ol5024568

data_1517664
_publ_contact_author
;
        Constantin G. Daniliuc
        Organisch-Chemisches Institut 
        Westf\"alische Wilhelm-Universit\"at M\"unster
        48149 M\"unster
        Germany
;
_publ_section_title
;
 Direct Conversion of Alcohols to \a-Chloro Aldehydes and \a-Chloro
 Ketones.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4932
_journal_page_last               4935
_journal_paper_doi               10.1021/ol5024568
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C27 H45 Cl O'
_chemical_formula_weight         421.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           'APEX2 v2014.5-0'
_audit_update_record
;
2012-05-10 # Formatted by publCIF
;
_cell_angle_alpha                90
_cell_angle_beta                 101.552(3)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   62.156(3)
_cell_length_b                   6.5176(3)
_cell_length_c                   18.9764(8)
_cell_measurement_reflns_used    107
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      24.7026
_cell_measurement_theta_min      6.7834
_cell_volume                     7531.8(6)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 V5-0/14 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'D8 Venture Dual Source'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1068
_diffrn_reflns_av_unetI/netI     0.1236
_diffrn_reflns_limit_h_max       68
_diffrn_reflns_limit_h_min       -68
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            29176
_diffrn_reflns_theta_full        59.03
_diffrn_reflns_theta_max         59.03
_diffrn_reflns_theta_min         2.38
_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_exptl_absorpt_coefficient_mu    1.434
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/2 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.114
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2784
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.396
_refine_ls_abs_structure_details
;
Flack x determined using 1604 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.062(16)
_refine_ls_extinction_coef       0.00008(4)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     992
_refine_ls_number_reflns         10179
_refine_ls_number_restraints     491
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1530
_refine_ls_R_factor_gt           0.0753
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1007P)^2^+5.0885P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1762
_refine_ls_wR_factor_ref         0.2199
_reflns_number_gt                5458
_reflns_number_total             10179
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5024568_si_002.cif
_cod_data_source_block           global
_cod_depositor_comments          'Adding full bibliography for 1517664.cif.'
_cod_database_code               1517664