A sterically encumbered photoredox catalyst enables the unified synthesis of the classical lignan family of natural products
Alfonzo, Edwin; Beeler, Aaron B.; Chemical Science  (2019) –; doi:10.1039/C9SC02682G

data_1551987
_publ_section_title
;
 A sterically encumbered photoredox catalyst enables the unified synthesis
 of the classical lignan family of natural products
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC02682G
_journal_year                    2019
_chemical_formula_moiety         'C32 H24 N2 O3'
_chemical_formula_sum            'C32 H24 N2 O3'
_chemical_formula_weight         484.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-31 deposited with the CCDC.    2019-07-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.137(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.638(3)
_cell_length_b                   9.9154(9)
_cell_length_c                   17.199(2)
_cell_measurement_reflns_used    2513
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      65.70
_cell_measurement_theta_min      5.17
_cell_volume                     4941.3(9)
_computing_cell_refinement       'APEX3 (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT (Bruker, 2016)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker X8 Proteum-R'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  Montel
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_unetI/netI     0.1099
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            59476
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.790
_diffrn_reflns_theta_max         66.790
_diffrn_reflns_theta_min         4.578
_diffrn_source                   'rotating anode'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  0.8403
_exptl_absorpt_correction_T_min  0.6502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 121173 reflections, Rint = 0.1178
 (63919 with I > 3sig(I), Rint = 0.1091)
;
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       prism
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.215
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     672
_refine_ls_number_reflns         59476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0752
_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^)+(0.1131P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2050
_refine_ls_wR_factor_ref         0.2197
_reflns_Friedel_coverage         0.000
_reflns_number_gt                47057
_reflns_number_total             59476
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {7b222626-4f9a-439b-9c9a-bb52e9823177}
_cod_data_source_file            c9sc02682g2.cif
_cod_data_source_block           twin4_transformed
_cod_original_cell_volume        4941.3(10)
_cod_database_code               1551987
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7386(19)
 0.2614(19)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C8A(H8A), C9A(H9A), C9B(H9B), C8B(H8B), C25A(H25A), C24A(H24A), C24B(H24B),
 C25B(H25B)
3.b Aromatic/amide H refined with riding coordinates:
 C31B(H31B), C3B(H3B), C4A(H4A), C10A(H10A), C30B(H30B), C11B(H11B),
 C30A(H30A), C31A(H31A), C7B(H7B), C6B(H6B), C4B(H4B), C27B(H27B), C28B(H28B),
 C11A(H11A), C3A(H3A), C6A(H6A), C10B(H10B), C19A(H19A), C7A(H7A), C27A(H27A),
 C16B(H16B), C19B(H19B), C28A(H28A), C16A(H16A), C18B(H18B), C17B(H17B),
 C17A(H17A), C18A(H18A)
3.c Idealised Me refined as rotating group:
 C32A(H32D,H32E,H32F), C32B(H32A,H32B,H32C), C1B(H1BA,H1BB,H1BC), C1A(H1AA,
 H1AB,H1AC)
;
_shelx_res_checksum              77053
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
;
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