Site-selective ring opening of bicyclo[n.1.0]alkanols: An Fe(II)-catalyzed 1,6-conjugate addition to p-quinone methides
Jha, Neha; Mondal, Subhadip; Kapur, Manmohan; Chemical Communications  (2023) –; doi:10.1039/D3CC04135B

data_7132153
_publ_section_title
;
 Site-selective ring opening of bicyclo[n.1.0]alkanols: An
 Fe(II)-catalyzed 1,6-conjugate addition to p-quinone methides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04135B
_journal_year                    2023
_chemical_formula_moiety         'C32 H37 Br O2'
_chemical_formula_sum            'C32 H37 Br O2'
_chemical_formula_weight         533.52
_chemical_name_systematic        NJ-02
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-08-05
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-08-07 deposited with the CCDC.	2023-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                91.085(8)
_cell_angle_beta                 93.650(8)
_cell_angle_gamma                91.818(8)
_cell_formula_units_Z            2
_cell_length_a                   8.8874(13)
_cell_length_b                   11.6780(17)
_cell_length_c                   12.9106(17)
_cell_measurement_reflns_used    2467
_cell_measurement_temperature    140.00
_cell_measurement_theta_max      78.42
_cell_measurement_theta_min      7.43
_cell_volume                     1336.3(3)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      140.00
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            36874
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.761
_diffrn_reflns_theta_min         6.240
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.291
_exptl_absorpt_correction_type   none
_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    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.121
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.897
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         5299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.162
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0607
_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^)+(0.0578P)^2^+3.0586P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1517
_refine_ls_wR_factor_ref         0.1546
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4788
_reflns_number_total             5299
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04135b2.cif
_cod_data_source_block           NJ-02
_cod_database_code               7132153
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.769
_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:
 C1(H1), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C12(H12A,H12B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C24(H24), C18(H18), C15(H15), C9(H9), C8(H8), C17(H17), C7(H7),
 C6(H6), C16(H16)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C31(H31A,H31B,H31C), C26(H26A,H26B,
 H26C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              1962
_shelx_hkl_checksum              42230
_olex2_submission_special_instructions 'No special instructions were received'