Robust and efficient transfer hydrogenation of carbonyl compounds catalyzed by NN-Mn(I) complexes
Wang, Zheng; Ma, Ning; Lu, Xiaochi; Liu, Ming; Liu, Tian; Liu, Qingbin; Solan, Gregory; Sun, Wen Hua; Dalton Transactions  (2023) –; doi:10.1039/D3DT02022C

data_7713442
_publ_section_title
;
 Robust and efficient transfer hydrogenation of carbonyl compounds
 catalyzed by NN-Mn(I) complexes
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT02022C
_journal_year                    2023
_chemical_formula_moiety         'C15 H18 Br Mn N2 O3'
_chemical_formula_sum            'C15 H18 Br Mn N2 O3'
_chemical_formula_weight         409.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-03-10
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2023-03-13 deposited with the CCDC.	2023-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.0588(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.7602(3)
_cell_length_b                   12.71564(11)
_cell_length_c                   16.6797(2)
_cell_measurement_reflns_used    10508
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      76.2840
_cell_measurement_theta_min      4.0770
_cell_volume                     4306.95(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.963
_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     48.00 117.00   0.50    0.10    --   47.70  51.00 -15.00  138
  2  \w    123.00 169.00   0.50    0.25    --  107.36  57.00-120.00   92
  3  \w    107.00 155.00   0.50    0.25    --  107.36  51.00 -15.00   96
  4  \w     35.00 102.00   0.50    0.25    --  107.36 -77.00 120.00  134
  5  \w    -15.00  58.00   0.50    0.10    --   47.70 -51.00-161.00  146
  6  \w     35.00  61.00   0.50    0.25    --  107.36 -51.00-161.00   52
  7  \w     55.00 102.00   0.50    0.25    --  107.36 -77.00 -90.00   94
  8  \w     73.00 102.00   0.50    0.25    --  107.36 -99.00-150.00   58
  9  \w     35.00  70.00   0.50    0.25    --  107.36 -99.00-150.00   70
 10  \w    -47.00  24.00   0.50    0.10    --  -47.70  51.00 -15.00  142
 11  \w    -99.00 -58.00   0.50    0.25    -- -104.50  77.00 120.00   82
 12  \w    -62.00 -37.00   0.50    0.25    -- -104.50  57.00 150.00   50
 13  \w    -62.00 -33.00   0.50    0.25    -- -104.50  57.00 120.00   58
 14  \w    -60.00 -32.00   0.50    0.25    -- -104.50  57.00  90.00   56
 15  \w   -101.00 -33.00   0.50    0.25    -- -104.50  77.00 -30.00  136
 16  \w    -62.00 -35.00   0.50    0.25    -- -104.50  57.00 -90.00   54
 17  \w    -61.00 -33.00   0.50    0.25    -- -104.50  57.00-150.00   56
 18  \w    -62.00 -32.00   0.50    0.25    -- -104.50  57.00-180.00   60
 19  \w    -61.00 -32.00   0.50    0.25    -- -104.50  57.00-120.00   58
 20  \w   -106.00 -33.00   0.50    0.25    -- -104.50 125.00 -30.00  146
 21  \w   -169.00-104.00   0.50    0.25    -- -104.50 -57.00 -60.00  130
 22  \w   -116.00 -91.00   0.50    0.10    --  -47.70-125.00 -30.00   50
 23  \w   -119.00 -75.00   0.50    0.10    --  -47.70-125.00 -60.00   88
 24  \w   -174.00-138.00   0.50    0.25    -- -104.50 -51.00-161.00   72
 25  \w    -83.00 -36.00   0.50    0.10    --  -47.70 -51.00-161.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0245643000
_diffrn_orient_matrix_UB_12      0.0014551000
_diffrn_orient_matrix_UB_13      0.0988893000
_diffrn_orient_matrix_UB_21      -0.0558356000
_diffrn_orient_matrix_UB_22      -0.0756871000
_diffrn_orient_matrix_UB_23      -0.0021533000
_diffrn_orient_matrix_UB_31      0.0451030000
_diffrn_orient_matrix_UB_32      -0.0945987000
_diffrn_orient_matrix_UB_33      0.0032868000
_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  0.0218
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15658
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.773
_diffrn_reflns_theta_min         4.102
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.247
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.816
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.000073(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         4369
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0522P)^2^+8.6056P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0962
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4156
_reflns_number_total             4369
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt02022c2.cif
_cod_data_source_block           Mn1
_cod_original_cell_volume        4306.96(9)
_cod_database_code               7713442
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N O Mn Br'
_shelx_estimated_absorpt_t_max   0.409
_shelx_estimated_absorpt_t_min   0.220
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), N2(H2), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C7(H7a,H7b), C6(H6a,H6b)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C2(H2a)
2.d Idealised Me refined as rotating group:
 C11(H11a,H11b,H11c), C12(H12a,H12b,H12c)
;
_shelx_res_checksum              15353
_shelx_fab_checksum              45902
_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 1.702
_oxdiff_exptl_absorpt_empirical_full_min 0.781