Manganese(I)-catalyzed nucleophilic addition of C(sp<sup>3</sup>)-H bonds to aldehydes.
Liu, Hongxin; Tang, Tingyu; Li, Bin; Wang, Baiquan; Chemical communications (Cambridge, England) 60 (2024) 5066–5069; doi:10.1039/d4cc01338g

data_7132960
_publ_section_title
;
 Manganese(I)-catalyzed nucleophilic addition of C(sp<sup>3</sup>)-H bonds
 to aldehydes.
;
_journal_issue                   38
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5066
_journal_page_last               5069
_journal_paper_doi               10.1039/d4cc01338g
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C14 H8 Mn N O4'
_chemical_formula_sum            'C14 H8 Mn N O4'
_chemical_formula_weight         309.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-28
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-28 deposited with the CCDC.	2024-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.411(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.63100(18)
_cell_length_b                   8.00772(17)
_cell_length_c                   20.9823(5)
_cell_measurement_reflns_used    7732
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.1870
_cell_measurement_theta_min      1.9530
_cell_volume                     1268.37(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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    -69.00  -5.00   1.00    1.00    --  -16.60 -70.00  90.00   64
  2  \w    -47.00  72.00   1.00    1.00    --  -16.60  70.00-150.00  119
  3  \w    -41.00  64.00   1.00    1.00    --  -16.60  38.00 -30.00  105
  4  \w   -101.00 -21.00   1.00    1.00    --  -16.60 -38.00-180.00   80
  5  \w     35.00  60.00   1.00    1.00    --  -16.60  38.00-150.00   25
  6  \w    -92.00 -66.00   1.00    1.00    --  -16.60 -19.00-180.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku MM007 Saturn944+'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0537879000
_diffrn_orient_matrix_UB_12      -0.0679174000
_diffrn_orient_matrix_UB_13      0.0069577000
_diffrn_orient_matrix_UB_21      0.0148672000
_diffrn_orient_matrix_UB_22      -0.0398856000
_diffrn_orient_matrix_UB_23      -0.0289119000
_diffrn_orient_matrix_UB_31      0.0756173000
_diffrn_orient_matrix_UB_32      -0.0404967000
_diffrn_orient_matrix_UB_33      0.0168270000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15318
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.569
_diffrn_reflns_theta_min         1.962
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.052
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3553
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0363
_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^)+(0.0520P)^2^+0.2185P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0970
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3235
_reflns_number_total             3553
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01338g2.cif
_cod_data_source_block           r20231115c
_cod_depositor_comments
'Adding full bibliography for 7132959--7132960.cif.'
_cod_database_code               7132960
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C15H12MnNO4
_shelx_estimated_absorpt_t_max   0.772
_shelx_estimated_absorpt_t_min   0.703
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C3(H3), C5(H5), C6(H6), C2(H2)
;
_shelx_res_checksum              29048
_shelx_hkl_checksum              91853
_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 1.465
_oxdiff_exptl_absorpt_empirical_full_min 0.521