Stereoselective synthesis of a Podophyllum lignan core by intramolecular reductive nickel-catalysis.
Xiao, Jian; Cong, Xiao-Wei; Yang, Gui-Zhen; Wang, Ya-Wen; Peng, Yu; Chemical communications (Cambridge, England) 54 (2018) 2040–2043; doi:10.1039/c8cc00001h

data_7121247
_publ_section_title
;
 Stereoselective synthesis of a Podophyllum lignan core by intramolecular
 reductive nickel-catalysis.
;
_journal_issue                   16
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2040
_journal_page_last               2043
_journal_paper_doi               10.1039/c8cc00001h
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C13 H15 F O2'
_chemical_formula_sum            'C13 H15 F O2'
_chemical_formula_weight         222.25
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-01-11
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2017-12-13 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                107.549(19)
_cell_angle_beta                 90.344(18)
_cell_angle_gamma                106.555(18)
_cell_formula_units_Z            2
_cell_length_a                   7.4670(16)
_cell_length_b                   8.1131(16)
_cell_length_c                   10.193(2)
_cell_measurement_reflns_used    833
_cell_measurement_temperature    273.77(10)
_cell_measurement_theta_max      23.5300
_cell_measurement_theta_min      4.2090
_cell_volume                     561.5(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      273.77(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -45.00   41.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -57.0000   30.0000 43

  2 omega  -10.00   24.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3041  -99.0000  -60.0000 17

  3 omega  -12.00   22.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3041  -99.0000   60.0000 17

  4 omega  -47.00   41.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -57.0000  150.0000 44

  5 omega  -46.00   42.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -57.0000  -90.0000 44

  6 omega   -8.00   24.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3041  -99.0000 -180.0000 16
;
_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      0.0881534000
_diffrn_orient_matrix_UB_12      0.0645019000
_diffrn_orient_matrix_UB_13      0.0291813000
_diffrn_orient_matrix_UB_21      0.0238688000
_diffrn_orient_matrix_UB_22      0.0011589000
_diffrn_orient_matrix_UB_23      -0.0670313000
_diffrn_orient_matrix_UB_31      -0.0397509000
_diffrn_orient_matrix_UB_32      0.0712879000
_diffrn_orient_matrix_UB_33      0.0059815000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3562
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.33
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2209
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0550
_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^)+(0.0400P)^2^+0.1096P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1404
_reflns_number_gt                1441
_reflns_number_total             2209
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc00001h2.cif
_cod_data_source_block           xiaojian1222
_cod_depositor_comments
'Adding full bibliography for 7121246--7121249.cif.'
_cod_database_code               7121247
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C8(H8), C9(H9), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_olex2_submission_special_instructions 'No special instructions were received'