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_1570535
_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         'C19 H16 Br Mn N2 O3 S'
_chemical_formula_sum            'C19 H16 Br Mn N2 O3 S'
_chemical_formula_weight         487.25
_chemical_name_systematic        Manganesepentacarbonylbromidequinolinethiophene
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-25
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-09-25 deposited with the CCDC.	2023-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.364(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2068(4)
_cell_length_b                   15.5782(5)
_cell_length_c                   9.4496(3)
_cell_measurement_reflns_used    13146
_cell_measurement_temperature    106(9)
_cell_measurement_theta_max      26.9610
_cell_measurement_theta_min      2.0250
_cell_volume                     1923.47(11)
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      106(9)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.957
_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    -44.00  22.00   0.50    4.00    --  -12.09  87.00  45.00  132
  2  \w    -42.00  11.00   0.50    4.00    --  -12.09 -87.00 -71.00  106
  3  \w    -38.00  29.00   0.50    4.00    --   12.09 -87.00 -71.00  134
  4  \w    -15.00  14.00   0.50    4.00    --  -12.09 -99.00-180.00   58
  5  \w     -5.00  22.00   0.50    4.00    --  -12.09 -99.00  90.00   54
  6  \w    -19.00  14.00   0.50    4.00    --  -12.09 -99.00-120.00   66
  7  \w    -17.00  19.00   0.50    4.00    --  -12.09 -99.00  30.00   72
  8  \w    -62.00 -10.00   0.50    4.00    --   12.09 -19.00 -30.00  104
  9  \w     12.00  37.00   0.50    4.00    --   12.09-125.00 -60.00   50
 10  \w    -51.00   0.00   0.50    4.00    --   12.09 -19.00 120.00  102
 11  \w    -62.00   3.00   0.50    4.00    --   12.09 -19.00-150.00  130
 12  \w     12.00  62.00   0.50    4.00    --   12.09-125.00 -90.00  100
 13  \w     15.00  41.00   0.50    4.00    --   12.09-125.00 150.00   52
 14  \w      1.00  26.00   0.50    4.00    --   12.09  38.00-120.00   50
 15  \w     27.00  70.00   0.50    4.00    --   12.09  38.00-120.00   86
 16  \w     12.00  57.00   0.50    4.00    --   12.09-125.00  30.00   90
 17  \w    -14.00  41.00   0.50    4.00    --   12.09 -99.00  60.00  110
 18  \w    -48.00  -4.00   0.50    4.00    --   12.09 -19.00  60.00   88
 19  \w    -59.00   4.00   0.50    4.00    --   12.09 -19.00-180.00  126
;
_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      -0.0223175000
_diffrn_orient_matrix_UB_12      0.0396620000
_diffrn_orient_matrix_UB_13      0.0155408000
_diffrn_orient_matrix_UB_21      -0.0435586000
_diffrn_orient_matrix_UB_22      -0.0093621000
_diffrn_orient_matrix_UB_23      -0.0509271000
_diffrn_orient_matrix_UB_31      -0.0235439000
_diffrn_orient_matrix_UB_32      -0.0202401000
_diffrn_orient_matrix_UB_33      0.0540608000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0989
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            24716
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.082
_diffrn_reflns_theta_min         2.034
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.894
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic orangish orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_preparation
'crystalisation have done in methanol and chloroform'
_exptl_crystal_recrystallization_method
'crystallisation have done in methanol and  chloroform?'
_exptl_crystal_size_max          0.002
_exptl_crystal_size_mid          0.002
_exptl_crystal_size_min          0.001
_refine_diff_density_max         1.631
_refine_diff_density_min         -1.024
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         4053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0504
_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^)+(0.0743P)^2^+5.1258P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1398
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3496
_reflns_number_total             4053
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05523j2.cif
_cod_data_source_block           ksk_k_mn4_mo_auto
_cod_depositor_comments
'Adding full bibliography for 1570534--1570535.cif.'
_cod_original_cell_volume        1923.46(11)
_cod_database_code               1570535
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'Mn C H N S O Br'
_chemical_oxdiff_usercomment     100K
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.994
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(C2)
Uanis(C1) = Uanis(O1)
3.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C13(H13), C12(H12), C16(H16), C19(H19), C17(H17), C9(H9), C18(H18),
 C10(H10)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_shelx_res_checksum              38087
_shelx_hkl_checksum              35656
_olex2_exptl_crystal_mounting_method Mo
_olex2_submission_original_sample_id KSK_KDK_KD_KC_Mn4
_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 1.813
_oxdiff_exptl_absorpt_empirical_full_min 0.535