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_7121249
_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         'C14 H16 O4'
_chemical_formula_sum            'C14 H16 O4'
_chemical_formula_weight         248.27
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2014-07-02
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Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
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_audit_update_record
;
2017-12-13 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.513(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0801(7)
_cell_length_b                   17.337(3)
_cell_length_c                   13.987(2)
_cell_measurement_reflns_used    1465
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4630
_cell_measurement_theta_min      4.0540
_cell_volume                     1226.2(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_ambient_temperature      293(2)
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_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details
;
  1 omega   35.00   62.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -90.0000 18

  2 omega  -67.00  -34.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -180.0000 22

  3 omega  -46.00   17.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   25.0000 -150.0000 42

  4 omega   33.00   60.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  150.0000 18

  5 omega   33.00   81.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -30.0000 32

  6 omega   72.00  106.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  150.0000 23

  7 omega   30.00  126.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   66.0000 -122.7986 64

  8 omega   50.00   75.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  120.0000 17

  9 omega   34.00   74.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  -60.0000 27

 10 omega   44.00   93.50   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  120.0000 33

 11 omega   49.00   76.00   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000   60.0000 18

 12 omega   72.00   99.00   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000  -90.0000 18

 13 omega   70.00  116.50   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  -30.0000 31

 14 omega  147.00  174.00   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -150.0000 18

 15 omega   39.00   88.50   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000 -180.0000 33

 16 omega   69.00  148.50   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000   90.0000 53

 17 omega   55.00   92.50   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000   60.0000 25

 18 omega   48.00   93.00   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000    0.0000 30

 19 omega  125.00  176.00   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -12.0000 -120.0000 34

 20 omega   36.00  117.00   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -12.0000 -120.0000 54
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.2430208000
_diffrn_orient_matrix_UB_12      0.0405115000
_diffrn_orient_matrix_UB_13      -0.0351408000
_diffrn_orient_matrix_UB_21      -0.0699176000
_diffrn_orient_matrix_UB_22      -0.0336199000
_diffrn_orient_matrix_UB_23      -0.1011657000
_diffrn_orient_matrix_UB_31      -0.1695581000
_diffrn_orient_matrix_UB_32      0.0717408000
_diffrn_orient_matrix_UB_33      -0.0274501000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4114
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.780
_diffrn_reflns_theta_min         4.072
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.811
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2298
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0671
_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^)+(0.1279P)^2^+0.1193P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1855
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_reflns_Friedel_coverage         0.000
_reflns_number_gt                1721
_reflns_number_total             2298
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc00001h2.cif
_cod_data_source_block           xiaojian0701
_cod_depositor_comments
'Adding full bibliography for 7121246--7121249.cif.'
_cod_database_code               7121249
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.65
_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:
 C9(H9), C10(H10), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C8(H8A,H8B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              5522
_olex2_submission_special_instructions 'No special instructions were received'