A Phosphine-Free Manganese Catalyst Enables Stereoselective Synthesis of (1 + n)-Membered Cycloalkanes from Methyl Ketones and 1,n-Diols
Jana, Akash; Das, Kuhali; Kundu, Abhishek; Thorve, Pradip Ramdas; Adhikari, Debashis; Maji, Biplab; ACS Catalysis  (2020) 2615–; doi:10.1021/acscatal.9b05567

data_4517392
_publ_section_title
;
 A Phosphine-Free Manganese Catalyst Enables Stereoselective Synthesis of
 (1 + n)-Membered Cycloalkanes from Methyl Ketones and 1,n-Diols
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              2615
_journal_paper_doi               10.1021/acscatal.9b05567
_journal_year                    2020
_chemical_formula_moiety         'C14 H12 Br Mn N2 O3 S'
_chemical_formula_sum            'C14 H12 Br Mn N2 O3 S'
_chemical_formula_weight         423.17
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-09-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                108.970(4)
_cell_angle_beta                 99.234(3)
_cell_angle_gamma                101.738(3)
_cell_formula_units_Z            2
_cell_length_a                   7.5394(3)
_cell_length_b                   9.7257(4)
_cell_length_c                   11.6722(5)
_cell_measurement_reflns_used    6184
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.1630
_cell_measurement_theta_min      4.1170
_cell_volume                     768.37(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
  1 omega  -59.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       26.2061  -77.0000 -150.0000 128

  2 omega  -55.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       26.2061  -38.0000   60.0000 137

  3 omega  -59.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       26.2061  -77.0000 -150.0000 128

  4 omega  -12.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       26.2061   57.0000   30.0000 114

  5 omega   57.00  150.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       67.1031  178.0000 -150.0000 93

  6 omega   20.00  147.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       67.1031   45.0000   90.0000 127

  7 omega  100.00  153.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       67.1031  111.0000  150.0000 53

  8 omega  100.00  153.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       67.1031  111.0000   90.0000 53

  9 omega   30.00  144.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       67.1031   61.0000  -30.0000 114

 10 omega  -18.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       67.1031  -77.0000  150.0000 128

 11 omega  100.00  153.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       67.1031  111.0000 -180.0000 53

 12 omega   24.00  152.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       67.1031   77.0000 -180.0000 128

 13 omega  102.00  155.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       67.1031   93.0000   60.0000 53

 14 omega   30.00  144.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       67.1031   61.0000 -120.0000 114

 15 omega   21.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000   90.0000 92

 16 omega   21.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000  -90.0000 92

 17 omega   25.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -32.0000 -120.0000 153

 18 omega   25.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   21.0000  150.0000 153

 19 omega   21.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -21.0000  120.0000 157

 20 omega   19.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -89.0000  -30.0000 139

 21 omega   21.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000 -120.0000 92

 22 omega  101.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   93.0000   60.0000 77

 23 omega   23.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 128

 24 omega   29.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -65.0000 -150.0000 116

 25 omega  101.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000 -180.0000 77

 26 omega   71.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   65.0000    0.0000 107

 27 omega   86.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  138.0000  150.0000 92

 28 omega   31.00  147.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -54.0000   90.0000 116

 29 omega   21.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000  150.0000 92

 30 omega  101.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000 -150.0000 77

 31 omega   69.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   54.0000  -60.0000 109

 32 omega  101.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000 -120.0000 77

 33 omega   24.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -116.0000   54.5835 93

 34 omega  -12.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       26.2061   57.0000  -60.0000 114

 35 omega  -12.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       26.2061   57.0000  120.0000 114

 36 omega  -17.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       26.2061   77.0000   30.0000 116

 37 omega  -17.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       26.2061   77.0000  150.0000 128
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0185188000
_diffrn_orient_matrix_UB_12      -0.0044604000
_diffrn_orient_matrix_UB_13      0.1320347000
_diffrn_orient_matrix_UB_21      -0.1779592000
_diffrn_orient_matrix_UB_22      0.0532941000
_diffrn_orient_matrix_UB_23      0.0091812000
_diffrn_orient_matrix_UB_31      -0.1196544000
_diffrn_orient_matrix_UB_32      -0.1657400000
_diffrn_orient_matrix_UB_33      -0.0565884000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7944
_diffrn_reflns_theta_full        66.13
_diffrn_reflns_theta_max         66.13
_diffrn_reflns_theta_min         4.13
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    11.425
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.829
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         3.229
_refine_diff_density_min         -1.584
_refine_diff_density_rms         0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2673
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0536
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0789P)^2^+5.1991P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1400
_reflns_number_gt                2635
_reflns_number_total             2673
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs9b05567_si_002.cif
_cod_data_source_block           ajaab_181acat
_cod_original_cell_volume        768.37(5)
_cod_database_code               4517392
_chemical_oxdiff_formula         'C H N O Mn S Br'
_reflns_odcompleteness_completeness 97.84
_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. Uiso/Uaniso restraints and constraints
Uanis(C8) = Uanis(C10) = Uanis(C11)
Uanis(C14) = Uanis(C12) = Uanis(C13)
Uanis(C5) = Uanis(C4) = Uanis(C3) = Uanis(C2) = Uanis(C1)
3.a Ternary CH refined with riding coordinates:
 N2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C2(H2A), C10(H10), C11(H11), C4(H4), C9(H9)
;
_olex2_date_sample_data_collection 2019-03-15
_olex2_submission_special_instructions 'No special instructions were received'