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_7129208
_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 H14 Br2 O2'
_chemical_formula_sum            'C16 H14 Br2 O2'
_chemical_formula_weight         398.09
_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             2021-03-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-05-10 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.6370(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.96300(10)
_cell_length_b                   6.03520(10)
_cell_length_c                   16.0210(2)
_cell_measurement_reflns_used    11898
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.9870
_cell_measurement_theta_min      2.7460
_cell_volume                     768.391(19)
_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 2018/2 (Sheldrick, 2018)'
_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 0.968
_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    113.00 139.00   0.50    0.20    --  105.44  30.00-101.00   52
  2  \w     48.00  97.00   0.50    0.05    --   46.62  30.00-101.00   98
  3  \w      4.00  29.00   0.50    0.05    --   46.62 -30.00  98.00   50
  4  \w     33.00  70.00   0.50    0.20    --  105.44-125.00  30.00   74
  5  \w     77.00 107.00   0.50    0.20    --  105.44-125.00  30.00   60
  6  \w     79.00 105.00   0.50    0.20    --  105.44 -94.00-150.00   52
  7  \w     44.00  70.00   0.50    0.20    --  105.44 -94.00-150.00   52
  8  \w     33.00  69.00   0.50    0.20    --  105.44 -61.00  60.00   72
  9  \w     35.00  72.00   0.50    0.20    --  105.44 -61.00 120.00   74
 10  \w     35.00  68.00   0.50    0.20    --  105.44 -61.00  90.00   66
 11  \w     36.00  65.00   0.50    0.20    --  105.44 -61.00 150.00   58
 12  \w     36.00  62.00   0.50    0.20    --  105.44 -61.00  30.00   52
 13  \w     35.00  63.00   0.50    0.20    --  105.44 -61.00-150.00   56
 14  \w     34.00  70.00   0.50    0.20    --  105.44 -61.00-180.00   72
 15  \w    -40.00  20.00   0.50    0.05    --  -46.62  38.00  30.00  120
 16  \w    -23.00  29.00   0.50    0.05    --  -46.62  19.00 -30.00  104
 17  \w    -33.00  27.00   0.50    0.05    --  -46.62  30.00-101.00  120
 18  \w    -66.00 -30.00   0.50    0.20    -- -100.00  61.00 -30.00   72
 19  \w    -58.00 -33.00   0.50    0.20    -- -100.00  61.00-120.00   50
 20  \w    -64.00 -38.00   0.50    0.20    -- -100.00  61.00   0.00   52
 21  \w    -55.00 -29.00   0.50    0.20    -- -100.00  61.00  30.00   52
 22  \w    -60.00 -35.00   0.50    0.20    -- -100.00  61.00  60.00   50
 23  \w    -69.00 -43.00   0.50    0.20    -- -100.00  61.00  90.00   52
 24  \w    -71.00 -33.00   0.50    0.05    --  -46.62 -30.00  98.00   76
 25  \w   -175.00 -86.00   0.50    0.20    -- -100.00 -30.00  98.00  178
 26  \w     52.00  77.00   0.50    0.05    --   46.37  30.00-101.00   50
 27  \w     23.00  80.00   0.50    0.05    --   46.37  77.00 -30.00  114
 28  \w     56.00  95.00   0.50    0.05    --   46.37  38.00 -60.00   78
 29  \w     31.00  74.00   0.50    0.05    --   46.37  57.00  60.00   86
 30  \w   -161.00-135.00   0.50    0.20    -- -100.00 -73.00   7.50   52
 31  \w   -105.00 -79.00   0.50    0.20    -- -100.00 -77.00   0.00   52
 32  \w   -105.00 -78.00   0.50    0.20    -- -100.00 -73.00   7.50   54
 33  \w   -128.00 -79.00   0.50    0.20    -- -100.00 -73.00 -22.52   98
 34  \w   -167.00 -88.00   0.50    0.20    -- -100.00 -15.00   0.00  158
 35  \w   -103.00 -77.00   0.50    0.20    -- -100.00 -77.00 -60.00   52
 36  \w   -111.00 -77.00   0.50    0.20    -- -100.00 -77.00  23.80   68
 37  \w   -111.00 -85.00   0.50    0.20    -- -100.00 -53.00  52.65   52
 38  \w   -109.00 -76.00   0.50    0.20    -- -100.00 -77.00  60.00   66
 39  \w   -111.00 -85.00   0.50    0.20    -- -100.00 -61.00  30.00   52
 40  \w   -102.00 -76.00   0.50    0.20    -- -100.00 -77.00  30.00   52
 41  \w   -144.00 -79.00   0.50    0.20    -- -100.00 -71.00  -0.31  130
 42  \w   -164.00-138.00   0.50    0.20    -- -100.00 -72.00 -12.33   52
 43  \w   -109.00 -78.00   0.50    0.20    -- -100.00 -72.00 -12.33   62
 44  \w   -171.00-145.00   0.50    0.20    -- -100.00 -54.00 -54.65   52
 45  \w   -117.00 -77.00   0.50    0.20    -- -100.00 -75.00 -25.56   80
 46  \w   -112.00 -77.00   0.50    0.20    -- -100.00 -76.00  16.00   70
 47  \w   -106.00 -81.00   0.50    0.20    -- -100.00 -67.00  64.68   50
 48  \w   -122.00 -85.00   0.50    0.20    -- -100.00 -54.00 -54.65   74
 49  \w   -154.00-128.00   0.50    0.20    -- -100.00 -77.00  60.00   52
 50  \w   -165.00 -86.00   0.50    0.20    -- -100.00 -58.00  17.24  158
 51  \w   -136.00 -82.00   0.50    0.20    -- -100.00 -61.00 -60.00  108
 52  \w   -103.00 -77.00   0.50    0.20    -- -100.00 -77.00 -30.00   52
 53  \w   -164.00-139.00   0.50    0.20    -- -100.00 -77.00  30.00   50
 54  \w     97.00 143.00   0.50    0.20    --  107.00  30.00-120.00   92
 55  \w     66.00 104.00   0.50    0.20    --  107.00 -77.00 -60.00   76
 56  \w     73.00  99.00   0.50    0.20    --  107.00 -77.00-180.00   52
 57  \w     35.00  60.00   0.50    0.20    --  107.00 -77.00-180.00   50
 58  \w     62.00  99.00   0.50    0.20    --  107.00-125.00  60.00   74
 59  \w     82.00 107.00   0.50    0.20    --  107.00 -77.00 120.00   50
 60  \w     39.00  69.00   0.50    0.20    --  107.00 -77.00 120.00   60
 61  \w     36.00  72.00   0.50    0.20    --  107.00 -61.00-120.00   72
 62  \w   -118.00 -30.00   0.50    0.05    --  -46.37 -57.00 -60.00  176
 63  \w   -118.00 -30.00   0.50    0.05    --  -46.37 -57.00  60.00  176
 64  \w   -118.00 -23.00   0.50    0.05    --  -46.37 -77.00  30.00  190
 65  \w   -118.00 -30.00   0.50    0.05    --  -46.37 -57.00-120.00  176
 66  \w   -118.00 -23.00   0.50    0.05    --  -46.37 -77.00-180.00  190
 67  \w     18.00  95.00   0.50    0.05    --   46.37-125.00  60.00  154
 68  \w     30.00  74.00   0.50    0.05    --   46.37  57.00 120.00   88
 69  \w     23.00 118.00   0.50    0.05    --   46.37  77.00-120.00  190
 70  \w     18.00  95.00   0.50    0.05    --   46.37-125.00 120.00  154
 71  \w     23.00 118.00   0.50    0.05    --   46.37  77.00 150.00  190
 72  \w    -20.00   5.00   0.50    0.05    --   46.37 -30.00  98.00   50
 73  \w   -103.00 -77.00   0.50    0.20    -- -100.00 -74.00 -16.96   52
;
_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      -0.0304032000
_diffrn_orient_matrix_UB_12      -0.0982294000
_diffrn_orient_matrix_UB_13      0.0865203000
_diffrn_orient_matrix_UB_21      -0.1912696000
_diffrn_orient_matrix_UB_22      0.0033820000
_diffrn_orient_matrix_UB_23      -0.0218939000
_diffrn_orient_matrix_UB_31      0.0104596000
_diffrn_orient_matrix_UB_32      -0.2355930000
_diffrn_orient_matrix_UB_33      -0.0361734000
_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  0.0519
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15800
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.041
_diffrn_reflns_theta_min         2.764
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63591
_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    1.721
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details
;
 Flack x determined using 1260 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3060
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0280
_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^)+(0.0184P)^2^+1.1540P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0673
_refine_ls_wR_factor_ref         0.0676
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.903
_reflns_number_gt                2989
_reflns_number_total             3060
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04534b2.cif
_cod_data_source_block           songxh_210301
_cod_database_code               7129208
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.731
_shelx_estimated_absorpt_t_min   0.555
_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 Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C2(H2), C15(H15), C5(H5), C3(H3), C14(H14), C6(H6)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              10108
_shelx_hkl_checksum              41855
_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 2.032
_oxdiff_exptl_absorpt_empirical_full_min 0.583