Ligand regulation for manganese-catalyzed enantioselective epoxidation of olefins without acid.
Xu, Daqian; Sun, Qiangsheng; Lin, Jin; Sun, Wei; Chemical communications (Cambridge, England) 56 (2020) 13101–13104; doi:10.1039/d0cc04440g

data_7127279
_publ_section_title
;
 Ligand regulation for manganese-catalyzed enantioselective epoxidation of
 olefins without acid.
;
_journal_issue                   86
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13101
_journal_page_last               13104
_journal_paper_doi               10.1039/d0cc04440g
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H34 Cl Mn N6 O5, Cl O4, C2 H3 N'
_chemical_formula_sum            'C28 H37 Cl2 Mn N7 O9'
_chemical_formula_weight         741.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-08-31
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-08-31 deposited with the CCDC.	2020-09-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.990(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.8444(8)
_cell_length_b                   14.0029(13)
_cell_length_c                   13.7453(13)
_cell_measurement_reflns_used    4539
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.73
_cell_measurement_theta_min      2.55
_cell_volume                     1676.5(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8554
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         1.504
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  0.8870
_exptl_absorpt_correction_T_min  0.8616
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            'clear dark brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             770
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2291 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         5863
_refine_ls_number_restraints     133
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0722P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1068
_reflns_Friedel_coverage         0.905
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                5305
_reflns_number_total             5863
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc04440g2.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'AD' was changed
to 'ad' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7127279.cif.
;
_cod_database_code               7127279
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.887
_shelx_estimated_absorpt_t_min   0.862
_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, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C2) \\sim
Ueq, Uanis(C6) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(N1) \\sim Ueq, Uanis(C12)
\\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C14B) \\sim Ueq, Uanis(C13B) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O5B) \\sim Ueq, Uanis(O6) \\sim Ueq, Uanis(O6B) \\sim Ueq, Uanis(O7)
\\sim Ueq, Uanis(O8) \\sim Ueq, Uanis(O7B) \\sim Ueq, Uanis(O5) \\sim Ueq: with
sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: O5(0.5) O5B(0.5) O6B(0.6) C13(0.45) H13A(0.45) H13B(0.45)
 C13B(0.55) H13C(0.55) H13D(0.55) C14(0.45) H14A(0.45) H14B(0.45) O6(0.5)
 O7B(0.5) O7(0.4) C14B(0.55) H14C(0.55) H14D(0.55)
4.a Rotating group:
 O9(H9A,H9B)
4.b Ternary CH refined with riding coordinates:
 C9(H9), C18(H18)
4.c Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,
 H15B), C16(H16A,H16B), C17(H17A,H17B), C13B(H13C,H13D), C14(H14A,H14B),
 C14B(H14C,H14D)
4.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C21(H21), C22(H22), C23(H23), C24(H24)
4.e Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              75897
_shelx_hkl_checksum              75651
_olex2_submission_special_instructions 'No special instructions were received'