Triphenylphosphine oxide-catalyzed stereoselective poly- and dibromination of unsaturated compounds
Tian-Yang Yu; Yao Wang; Xiu-Qin Hu; Peng-Fei Xu; Chem.Commun. 50 (2014) 7817–; doi:10.1039/C4CC02847C

data_7115270
_publ_section_title
;
 Triphenylphosphine oxide-catalyzed stereoselective poly- and
 dibromination of unsaturated compounds
;
_journal_name_full               Chem.Commun.
_journal_page_first              7817
_journal_paper_doi               10.1039/C4CC02847C
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C11 H10 Br2 O3'
_chemical_formula_sum            'C11 H10 Br2 O3'
_chemical_formula_weight         350.01
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-09-09
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.6547(13)
_cell_length_b                   14.1169(10)
_cell_length_c                   16.8780(13)
_cell_measurement_reflns_used    1600
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.8560
_cell_measurement_theta_min      3.6560
_cell_volume                     2538.6(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9844
_diffrn_measured_fraction_theta_max 0.8948
_diffrn_measurement_details
;
  1 omega  -12.00   91.50   1.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   77.0000  -60.0000 69

  2 omega   -9.00   46.50   1.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512   19.0000  -60.0000 37

  3 omega   50.00   75.50   1.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6512  160.0000  132.0000 17
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0372334000
_diffrn_orient_matrix_UB_12      -0.0063691000
_diffrn_orient_matrix_UB_13      -0.0344141000
_diffrn_orient_matrix_UB_21      -0.0530258000
_diffrn_orient_matrix_UB_22      -0.0184296000
_diffrn_orient_matrix_UB_23      -0.0203797000
_diffrn_orient_matrix_UB_31      -0.0155702000
_diffrn_orient_matrix_UB_32      0.0462586000
_diffrn_orient_matrix_UB_33      -0.0128897000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_av_unetI/netI     0.0839
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7163
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.13
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    6.375
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.2900
_exptl_crystal_size_mid          0.2500
_exptl_crystal_size_min          0.2400
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2479
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1172
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0442P)^2^+0.6188P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1486
_reflns_number_gt                1274
_reflns_number_total             2479
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc02847c2.cif
_cod_data_source_block           yuty0905
_cod_original_cell_volume        2538.7(4)
_cod_database_code               7115270
_reflns_odcompleteness_completeness 98.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;