Catalyst-Controlled Chemodivergent Synthesis of Spirochromans from Diarylideneacetones and Organoboronic Acids
Liu, Na; Zhu, Wanjiang; Yao, Jian; Yin, Long; Lu, Tao; Dou, Xiaowei; ACS Catalysis 10 (2020) 2596–2602; doi:10.1021/acscatal.9b05577

data_4517385
_publ_section_title
;
 Catalyst-Controlled Chemodivergent Synthesis of Spirochromans from
 Diarylideneacetones and Organoboronic Acids
;
_journal_issue                   4
_journal_name_full               'ACS Catalysis'
_journal_page_first              2596
_journal_page_last               2602
_journal_paper_doi               10.1021/acscatal.9b05577
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C53 H42 O2 P2'
_chemical_formula_sum            'C53 H42 O2 P2'
_chemical_formula_weight         772.80
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 104.694(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.8900(4)
_cell_length_b                   21.1643(11)
_cell_length_c                   11.0358(5)
_cell_measurement_reflns_used    4603
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.350
_cell_measurement_theta_min      2.369
_cell_volume                     2008.48(17)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 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      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0739
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17647
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.400
_diffrn_reflns_theta_min         2.368
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0807 before and 0.0624 after correction. The Ratio of minimum to maximum transmission is 0.9378. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       block
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 2146 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     514
_refine_ls_number_reflns         7306
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0406P)^2^+0.1975P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.1004
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.804
_reflns_Friedel_fraction_max     0.773
_reflns_number_gt                6059
_reflns_number_total             7306
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b05577_si_003.cif
_cod_data_source_block           220191102d_0m
_cod_depositor_comments
;Adding full bibliography for 4517383--4517385.cif.

 Adding full bibliography for 4517383--4517385.cif.
;
_cod_database_code               4517385
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C29(H29), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C3(H3), C16(H16), C4(H4), C2(H2), C41(H41), C10(H10), C22(H22),
 C5(H5), C9(H9), C33(H33), C15(H15), C26(H26), C43(H43), C53(H53), C6(H6),
 C8(H8), C24(H24), C23(H23), C12(H12), C25(H25), C49(H49), C11(H11), C40(H40),
 C47(H47), C34(H34), C35(H35), C39(H39), C37(H37), C50(H50), C51(H51), C52(H52),
  C38(H38), C44(H44), C46(H46), C45(H45)
;
_olex2_submission_special_instructions 'No special instructions were received'