Raising the Ceiling of Diastereoselectivity in Hydrogen Transfer on Acyclic Radicals
Irina Denissova; Luca Maretti; Brian C. Wilkes; J.C. Scaiano; Yvan Guindon; Journal of Organic Chemistry 74 (2009) 2438–2446; doi:10.1021/jo802634w

data_4024398
_publ_contact_author_address
;
      IRCM
      110 ouest, Avenue des Pins     
      Montr\'eal, Qu\'ebec
      Canada H2W 1R7

;
_publ_contact_author_email       guindoy@ircm.qc.ca
_publ_contact_author_fax         '+1 514 987 5789'
_publ_contact_author_name        'Dr. Yvan Guindon'
_publ_contact_author_phone       '+1 514 987 5788'
_publ_section_title
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Raising the Ceiling of Diastereoselectivity in Hydrogen Transfer on Acyclic
Radicals
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_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2438
_journal_page_last               2446
_journal_paper_doi               10.1021/jo802634w
_journal_volume                  74
_journal_year                    2009
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C15 H21 Br O3'
_chemical_formula_sum            'C15 H21 Br O3'
_chemical_formula_weight         329.23
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 98.553(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.6579(7)
_cell_length_b                   6.1850(3)
_cell_length_c                   15.0265(6)
_cell_measurement_reflns_used    7204
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.2
_cell_measurement_theta_min      2.6
_cell_volume                     1530.95(12)
_computing_cell_refinement       'APEX2(Bruker, 2006)'
_computing_data_collection       'APEX2(Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 5.5
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Smart 6000'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  'Montel 200 optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19418
_diffrn_reflns_theta_full        72.52
_diffrn_reflns_theta_max         72.52
_diffrn_reflns_theta_min         2.68
_diffrn_standards_decay_%        0.00
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    3.677
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick,2004)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3027
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0276
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0382P)^2^+0.3289P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0737
_reflns_number_gt                2677
_reflns_number_total             3027
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo802634w_si_002.cif
_cod_data_source_block           guin48
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (19
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (26
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (31 time).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4024398