Dibrominated Addition and Substitution of Alkenes Catalyzed by Mn2(CO)10
Song, Xianheng; Meng, Shanshui; Zhang, Hong; Jiang, Yi; Chan, Albert S. C.; Zou, Yong; Chemical Communications  (2021) –; doi:10.1039/D1CC04534B

data_7129209
_publ_section_title
;
 Dibrominated Addition and Substitution of Alkenes Catalyzed by Mn2(CO)10
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC04534B
_journal_year                    2021
_chemical_formula_moiety         'C16 H13 Br3 O2'
_chemical_formula_sum            'C16 H13 Br3 O2'
_chemical_formula_weight         476.99
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-05-10 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.308(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.5472(2)
_cell_length_b                   7.8195(4)
_cell_length_c                   18.3327(7)
_cell_measurement_reflns_used    2544
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.5100
_cell_measurement_theta_min      2.4020
_cell_volume                     792.96(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    127.00 157.00   0.50    0.05    --  105.44  62.00 132.00   60
  2  \w    147.00 176.00   0.50    0.05    --  105.44  45.00  60.00   58
  3  \w     98.00 143.00   0.50    0.05    --  105.44  45.00  60.00   90
  4  \w     88.00 142.00   0.50    0.05    --  105.44  15.00-120.00  108
  5  \w     44.00 106.00   0.50    0.05    --  105.44 -77.00  60.00  124
  6  \w    -10.00  28.00   0.50    0.05    --   46.62 -62.00  -5.00   76
  7  \w     33.00  73.00   0.50    0.05    --  105.44 -61.00 150.00   80
  8  \w     33.00  74.00   0.50    0.05    --  105.44 -62.00  -5.00   82
  9  \w     55.00  90.00   0.50    0.05    --  105.44 -77.00-120.00   70
 10  \w     40.00  70.00   0.50    0.05    --  105.44 -61.00 -90.00   60
 11  \w     43.00  69.00   0.50    0.05    --  105.44-125.00-150.00   52
 12  \w    -63.00 -34.00   0.50    0.05    -- -100.00  62.00 132.00   58
 13  \w    -64.00  23.00   0.50    0.05    --  -46.62  62.00 132.00  174
 14  \w    -58.00 -33.00   0.50    0.05    -- -100.00  61.00  90.00   50
 15  \w    -66.00 -30.00   0.50    0.05    -- -100.00  61.00 -90.00   72
 16  \w     75.00 101.00   0.50    0.05    --  105.44-125.00-150.00   52
 17  \w    -94.00 -34.00   0.50    0.05    --  -46.62 -62.00  -5.00  120
 18  \w   -106.00 -76.00   0.50    0.05    --  -46.62-125.00  60.00   60
 19  \w   -118.00 -77.00   0.50    0.05    --  -46.62-125.00 150.00   82
 20  \w   -170.00-107.00   0.50    0.05    -- -100.00 -94.00  90.00  126
 21  \w   -172.00 -82.00   0.50    0.05    -- -100.00 -62.00  -5.00  180
 22  \w   -118.00 -91.00   0.50    0.05    --  -46.37 -62.00  -5.00   54
 23  \w     33.00 114.00   0.50    0.05    --   46.37  57.00-120.00  162
 24  \w   -170.00-145.00   0.50    0.05    -- -100.00 -61.00-120.00   50
 25  \w   -163.00 -85.00   0.50    0.05    -- -100.00 -15.00 -90.00  156
 26  \w   -101.00 -76.00   0.50    0.05    -- -100.00 -77.00 -30.00   50
 27  \w   -112.00 -86.00   0.50    0.05    -- -100.00 -61.00-120.00   52
 28  \w    140.00 166.00   0.50    0.05    --  107.00  77.00-120.00   52
 29  \w    100.00 136.00   0.50    0.05    --  107.00  45.00  30.00   72
 30  \w    106.00 134.00   0.50    0.05    --  107.00  77.00-120.00   56
 31  \w    126.00 153.00   0.50    0.05    --  107.00  77.00-180.00   54
 32  \w     83.00 109.00   0.50    0.05    --  107.00  77.00-180.00   52
 33  \w     94.00 166.00   0.50    0.05    --  107.00  30.00 -90.00  144
 34  \w    149.00 177.00   0.50    0.05    --  107.00  45.00  30.00   56
 35  \w     38.00  64.00   0.50    0.05    --  107.00 -61.00 120.00   52
 36  \w     42.00  68.00   0.50    0.05    --  107.00 -94.00 -60.00   52
 37  \w     81.00 106.00   0.50    0.05    --  107.00 -94.00  60.00   50
 38  \w    122.00 150.00   0.50    0.05    --  107.00  45.00  90.00   56
 39  \w     69.00  94.00   0.50    0.05    --  107.00 -94.00 -60.00   50
 40  \w     35.00  62.00   0.50    0.05    --  107.00 -94.00  60.00   54
 41  \w     35.00  61.00   0.50    0.05    --  107.00 -61.00-150.00   52
 42  \w     94.00 160.00   0.50    0.05    --  107.00  77.00 120.00  132
 43  \w     77.00 104.00   0.50    0.05    --  107.00 -94.00  30.00   54
 44  \w     96.00 125.00   0.50    0.05    --  107.00  45.00 -90.00   58
 45  \w     38.00  83.00   0.50    0.05    --  107.00 -94.00 -30.00   90
 46  \w     83.00 174.00   0.50    0.05    --  107.00  77.00-150.00  182
 47  \w     29.00 118.00   0.50    0.05    --   46.37  62.00 132.00  178
 48  \w     23.00 118.00   0.50    0.05    --   46.37  77.00  30.00  190
 49  \w     30.00 118.00   0.50    0.05    --   46.37  57.00-150.00  176
 50  \w     23.00 118.00   0.50    0.05    --   46.37  77.00 -30.00  190
 51  \w     18.00  95.00   0.50    0.05    --   46.37-125.00   0.00  154
 52  \w     23.00 118.00   0.50    0.05    --   46.37  77.00-150.00  190
 53  \w     30.00 118.00   0.50    0.05    --   46.37  57.00 -60.00  176
 54  \w   -173.00 -80.00   0.50    0.05    -- -100.00 -77.00 150.00  186
 55  \w   -172.00 -85.00   0.50    0.05    -- -100.00 -45.00 -90.00  174
 56  \w   -173.00 -82.00   0.50    0.05    -- -100.00 -61.00-180.00  182
 57  \w   -173.00 -76.00   0.50    0.05    -- -100.00 -77.00  60.00  194
 58  \w     34.00 112.00   0.50    0.05    --  107.00-125.00  30.00  156
 59  \w     92.00 178.00   0.50    0.05    --  107.00  30.00 120.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2172560000
_diffrn_orient_matrix_UB_12      -0.0633704000
_diffrn_orient_matrix_UB_13      -0.0500641000
_diffrn_orient_matrix_UB_21      -0.0640660000
_diffrn_orient_matrix_UB_22      -0.1280248000
_diffrn_orient_matrix_UB_23      0.0593796000
_diffrn_orient_matrix_UB_31      -0.1620416000
_diffrn_orient_matrix_UB_32      0.1356504000
_diffrn_orient_matrix_UB_33      0.0327307000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1869
_diffrn_reflns_av_unetI/netI     0.1175
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16382
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.846
_diffrn_reflns_theta_min         2.417
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    9.447
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.998
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.009
_refine_diff_density_min         -1.626
_refine_diff_density_rms         0.190
_refine_ls_abs_structure_details
;
 Flack x determined using 726 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3232
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0697
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0675P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1568
_refine_ls_wR_factor_ref         0.1783
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                2401
_reflns_number_total             3232
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04534b2.cif
_cod_data_source_block           songxh_cl_210208_2
_cod_database_code               7129209
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHONClBr
_shelx_estimated_absorpt_t_max   0.452
_shelx_estimated_absorpt_t_min   0.201
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C2(H2), C6(H6), C18(H18), C16(H16), C5(H5), C19(H19), C15(H15), C3(H3)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              52359
_shelx_hkl_checksum              66564
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.400
_oxdiff_exptl_absorpt_empirical_full_min 0.414