Mn(I)-Catalyzed Nucleophilic Addition/Ring Expansion via C-H Activation and C-C Cleavage
Liu, Bingxian; Yuan, Yin; Hu, Panjie; zheng, guangfan; Bai, Da-Chang; Chang, Junbiao; Li, Xingwei; Chemical Communications  (2019) –; doi:10.1039/C9CC05973C

data_7124010
_publ_section_title
;
 Mn(I)-Catalyzed Nucleophilic Addition/Ring Expansion via C-H Activation
 and C-C Cleavage
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05973C
_journal_year                    2019
_chemical_formula_moiety         'C21 H19 N3 O2'
_chemical_formula_sum            'C21 H19 N3 O2'
_chemical_formula_weight         345.39
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-21 deposited with the CCDC.    2019-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.7930(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7994(2)
_cell_length_b                   7.81190(10)
_cell_length_c                   19.9950(3)
_cell_measurement_reflns_used    5284
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      71.1660
_cell_measurement_theta_min      4.1310
_cell_volume                     1678.24(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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_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    -52.00  32.00   1.00    1.00    --  -35.37  57.00 -90.00   84
  2  \w      1.00  74.00   1.00    1.00    --   35.37 -99.00 -90.00   73
  3  \w    -32.00  52.00   1.00    1.00    --   35.37 -57.00  30.00   84
  4  \w     23.00  89.00   1.00    1.00    --   35.37-125.00-180.00   66
  5  \w     19.00 103.00   1.00    1.00    --   35.37  57.00   0.00   84
  6  \w     89.00 175.00   1.00    1.00    --  106.50  45.00 -90.00   86
  7  \w     37.00 112.00   1.00    1.00    --  106.50-111.00 150.00   75
  8  \w     80.00 174.00   1.00    1.00    --  106.50  77.00-150.00   94
  9  \w    100.00 176.00   1.00    1.00    --  106.50 111.00-180.00   76
 10  \w     37.00 109.00   1.00    1.00    --  106.50 -95.00   0.00   72
 11  \w     37.00 112.00   1.00    1.00    --  106.50-111.00 -90.00   75
 12  \w     37.00 128.00   1.00    1.00    --  106.50 -30.00-180.00   91
 13  \w     39.00 133.00   1.00    1.00    --  106.50 -77.00  90.00   94
 14  \w    100.00 176.00   1.00    1.00    --  106.50 111.00  60.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1004169000
_diffrn_orient_matrix_UB_12      0.1300946000
_diffrn_orient_matrix_UB_13      0.0267601000
_diffrn_orient_matrix_UB_21      0.0953153000
_diffrn_orient_matrix_UB_22      -0.1463108000
_diffrn_orient_matrix_UB_23      0.0117751000
_diffrn_orient_matrix_UB_31      0.0374754000
_diffrn_orient_matrix_UB_32      0.0245280000
_diffrn_orient_matrix_UB_33      -0.0716422000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8623
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.329
_diffrn_reflns_theta_min         4.445
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87354
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3210
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0569P)^2^+0.8073P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1159
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2893
_reflns_number_total             3210
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05973c2.cif
_cod_data_source_block           lbx-20181204
_cod_database_code               7124010
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.918
_shelx_estimated_absorpt_t_min   0.813
_reflns_odcompleteness_completeness 99.97
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C19(H19A,H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C3(H3), C8(H8), C5(H5), C7(H7), C6(H6), C14(H14), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_shelx_res_checksum              37244
_olex2_date_sample_data_collection 2018-12-04
_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 1.219
_oxdiff_exptl_absorpt_empirical_full_min 0.869