Catalytic asymmetric aldehyde prenylation and application in the total synthesis of (-)-rosiridol and (-)-bifurcadiol.
Zhang, Yu-Long; Zhao, Zhen-Ni; Li, Wang-Lai; Li, Jing-Jie; Kalita, Subarna Jyoti; Schneider, Uwe; Huang, Yi-Yong; Chemical communications (Cambridge, England) 56 (2020) 10030–10033; doi:10.1039/d0cc00367k

data_7126944
_publ_section_title
;
 Catalytic asymmetric aldehyde prenylation and application in the total
 synthesis of (-)-rosiridol and (-)-bifurcadiol.
;
_journal_issue                   69
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10030
_journal_page_last               10033
_journal_paper_doi               10.1039/d0cc00367k
_journal_volume                  56
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H15 Br O3'
_chemical_formula_sum            'C13 H15 Br O3'
_chemical_formula_weight         299.16
_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     direct
_audit_creation_date             2019-06-24
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_audit_update_record
;
2019-12-02 deposited with the CCDC.	2020-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.046(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.8308(5)
_cell_length_b                   4.8800(2)
_cell_length_c                   12.3237(6)
_cell_measurement_reflns_used    3360
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.93
_cell_measurement_theta_min      3.84
_cell_volume                     664.04(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4261
_diffrn_reflns_point_group_measured_fraction_full 0.877
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        63.911
_diffrn_reflns_theta_max         63.911
_diffrn_reflns_theta_min         3.843
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.184
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.1807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.150
_refine_diff_density_min         -0.908
_refine_diff_density_rms         0.149
_refine_ls_abs_structure_details
; 
 Flack x determined using 630 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.19(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1931
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0687
_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^)+(0.1272P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1703
_refine_ls_wR_factor_ref         0.1724
_reflns_Friedel_coverage         0.609
_reflns_Friedel_fraction_full    0.764
_reflns_Friedel_fraction_max     0.764
_reflns_number_gt                1817
_reflns_number_total             1931
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc00367k2.cif
_cod_data_source_block           cu_190531b_0m
_cod_depositor_comments          'Adding full bibliography for 7126944.cif.'
_cod_database_code               7126944
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.680
_shelx_estimated_absorpt_t_min   0.634
_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) groups 
2.a Ternary CH refined with riding coordinates: 
 C8(H8) 
2.b Secondary CH2 refined with riding coordinates: 
 C1(H1A,H1B), C9(H9A,H9B) 
2.c Aromatic/amide H refined with riding coordinates: 
 C4(H4), C7(H7), C10(H10) 
2.d Idealised Me refined as rotating group: 
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C) 
2.e Idealised tetrahedral OH refined as rotating group: 
 O3(H3) 
;
_olex2_submission_special_instructions 'No special instructions were received'