Catalytic acceptorless dehydrogenative borylation of styrenes enabled by a molecularly defined manganese complex.
Das, Kuhali; Kundu, Abhishek; Sarkar, Koushik; Adhikari, Debashis; Maji, Biplab; Chemical science 15 (2024) 1098–1105; doi:10.1039/d3sc05523j

data_1570534
_publ_section_title
;
 Catalytic acceptorless dehydrogenative borylation of styrenes enabled by
 a molecularly defined manganese complex.
;
_journal_issue                   3
_journal_name_full               'Chemical science'
_journal_page_first              1098
_journal_page_last               1105
_journal_paper_doi               10.1039/d3sc05523j
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C18 H14 Br Mn N2 O3 S'
_chemical_formula_sum            'C18 H14 Br Mn N2 O3 S'
_chemical_formula_weight         473.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-07-25
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-07-25 deposited with the CCDC.	2023-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                104.364(2)
_cell_angle_beta                 97.514(2)
_cell_angle_gamma                93.655(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6734(2)
_cell_length_b                   11.8500(3)
_cell_length_c                   13.3321(3)
_cell_measurement_reflns_used    9103
_cell_measurement_temperature    100.00(13)
_cell_measurement_theta_max      67.9310
_cell_measurement_theta_min      3.4580
_cell_volume                     1158.45(5)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_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    -37.00  27.00   0.50    0.38    --  -41.33  32.00 -30.00  128
  2  \w    -24.00  35.00   0.50    0.38    --  -41.33  11.00 -90.00  118
  3  \w    -28.00  30.00   0.50    0.38    --  -41.33  21.00  30.00  116
  4  \w    -47.00 -15.00   0.50    2.00    --  -82.50  42.00  30.00   64
  5  \w    -47.00 -15.00   0.50    2.00    --  -82.50  42.00   0.00   64
  6  \w    -65.00  26.00   0.50    0.38    --  -41.33  65.00  30.00  182
  7  \w    -48.00  26.00   0.50    0.38    --  -41.33  43.00-180.00  148
  8  \w     25.00 109.00   0.50    0.38    --   41.33  43.00-180.00  168
  9  \w     73.00 165.00   0.50    2.00    --   96.67  68.00 -60.00  184
 10  \w    105.00 170.00   0.50    2.00    --   96.67  96.00-180.00  130
 11  \w     99.00 164.00   0.50    2.00    --   96.67 117.00-120.00  130
 12  \w     99.00 164.00   0.50    2.00    --   96.67 117.00-180.00  130
 13  \w     99.00 164.00   0.50    2.00    --   96.67 117.00 -60.00  130
 14  \w    101.00 164.00   0.50    2.00    --   96.67 114.00  44.00  126
 15  \w     80.00 163.00   0.50    2.00    --   96.67  42.00 -90.00  166
 16  \w     81.00 164.00   0.50    2.00    --   96.67 145.00-180.00  166
 17  \w     70.00 165.00   0.50    2.00    --   96.67  77.00-180.00  190
 18  \w     70.00 165.00   0.50    2.00    --   96.67  77.00 -90.00  190
 19  \w     71.00 170.00   0.50    2.00    --   96.67  17.00  30.00  198
 20  \w     41.00 100.00   0.50    0.38    --   41.33-138.00-180.00  118
 21  \w     41.00 100.00   0.50    0.38    --   41.33-138.00 -90.00  118
 22  \w     44.00 127.00   0.50    2.00    --   96.67-145.00-120.00  166
 23  \w     29.00 110.00   0.50    2.00    --   96.67-114.00 -46.00  162
 24  \w     26.00  85.00   0.50    0.38    --   41.33-114.00 -46.00  118
 25  \w     28.00 105.00   0.50    2.00    --   96.67 -77.00 -60.00  154
 26  \w     30.00  57.00   0.50    2.00    --   96.67 -50.00 -30.00   54
 27  \w     29.00  68.00   0.50    2.00    --   96.67 -59.00   0.00   78
 28  \w     29.00  68.00   0.50    2.00    --   96.67 -59.00 -30.00   78
 29  \w     29.00  68.00   0.50    2.00    --   96.67 -59.00 -60.00   78
 30  \w     30.00 109.00   0.50    2.00    --   96.67-117.00 -90.00  158
 31  \w     30.00 109.00   0.50    2.00    --   96.67-117.00  60.00  158
 32  \w     44.00 127.00   0.50    2.00    --   96.67-145.00 150.00  166
 33  \w     29.00  68.00   0.50    2.00    --   96.67 -59.00  90.00   78
 34  \w     27.00 127.00   0.50    2.00    --   96.67 -87.00 150.00  200
 35  \w     30.00  57.00   0.50    2.00    --   96.67 -50.00 120.00   54
 36  \w     22.00 106.00   0.50    2.00    --   96.67 -96.00 120.00  168
 37  \w     29.00  68.00   0.50    2.00    --   96.67 -59.00-150.00   78
 38  \w     30.00  57.00   0.50    2.00    --   96.67 -50.00-180.00   54
 39  \w     28.00 105.00   0.50    2.00    --   96.67 -77.00-180.00  154
 40  \w    -83.00  -4.00   0.50    0.38    --  -41.33 114.00  44.00  158
 41  \w    -83.00 -15.00   0.50    2.00    --  -82.50 114.00  44.00  136
 42  \w   -109.00 -28.00   0.50    0.38    --  -41.33 -32.00-120.00  162
 43  \w   -110.00 -14.00   0.50    0.38    --  -41.33 -77.00 -90.00  192
 44  \w   -108.00 -21.00   0.50    0.38    --  -41.33 -54.00   0.00  174
 45  \w   -109.00 -28.00   0.50    0.38    --  -41.33 -32.00  90.00  162
 46  \w   -110.00 -14.00   0.50    0.38    --  -41.33 -77.00 -30.00  192
 47  \w   -109.00 -18.00   0.50    0.38    --  -41.33 -65.00-180.00  182
 48  \w   -110.00 -14.00   0.50    0.38    --  -41.33 -77.00-120.00  192
 49  \w   -110.00 -14.00   0.50    0.38    --  -41.33 -77.00  60.00  192
 50  \w   -110.00 -14.00   0.50    0.38    --  -41.33 -77.00 120.00  192
 51  \w   -110.00 -14.00   0.50    0.38    --  -41.33 -77.00   0.00  192
 52  \w   -110.00 -14.00   0.50    0.38    --  -41.33 -77.00  90.00  192
 53  \w   -150.00 -79.00   0.50    2.00    --  -82.50-114.00 -46.00  142
 54  \w   -150.00 -69.00   0.50    2.00    --  -82.50 -33.00   0.00  162
 55  \w   -157.00 -83.00   0.50    2.00    --  -82.50 -96.00  90.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0421207000
_diffrn_orient_matrix_UB_12      0.0564566000
_diffrn_orient_matrix_UB_13      0.1187974000
_diffrn_orient_matrix_UB_21      0.1957539000
_diffrn_orient_matrix_UB_22      -0.0205975000
_diffrn_orient_matrix_UB_23      -0.0026148000
_diffrn_orient_matrix_UB_31      0.0364682000
_diffrn_orient_matrix_UB_32      0.1207506000
_diffrn_orient_matrix_UB_33      -0.0210545000
_diffrn_radiation_monochromator  mirror
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_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16706
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.261
_diffrn_reflns_theta_min         3.462
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.640
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67233
_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            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.227
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4196
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0789P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1128
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3820
_reflns_number_total             4196
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05523j2.cif
_cod_data_source_block           kd-179
_cod_depositor_comments
'Adding full bibliography for 1570534--1570535.cif.'
_cod_database_code               1570534
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N S Mn Br'
_chemical_oxdiff_usercomment     100K
_shelx_estimated_absorpt_t_max   0.803
_shelx_estimated_absorpt_t_min   0.515
_diffrn_oxdiff_digest_frames
;
0148af9e8848898d4cb12fc3c7b66158c5000307e5f
;
_diffrn_oxdiff_digest_hkl
;
013e3feaac5b57877dd6e6d2da697d9ca34d01
;
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2a), C5(H5), C3(H3), C4(H4), C8(H8), C7(H7), C13(H13), C14(H14), C15(H15)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              92112
_shelx_hkl_checksum              1565
_shelx_fab_checksum              76532
_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 1.641
_oxdiff_exptl_absorpt_empirical_full_min 0.620