Total synthesis of linoxepin facilitated by Ni-catalyzed tandem reductive cyclization
Cao, Jing-Si; Zeng, Jing; Xiao, Jian; Wang, Xiao-Han; Wang, Yawen; Peng, Yu; Chemical Communications  (2022) –; doi:10.1039/D2CC02221D

data_7130173
_publ_section_title
;
 Total synthesis of linoxepin facilitated by Ni-catalyzed tandem reductive
 cyclization
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02221D
_journal_year                    2022
_chemical_formula_moiety         'C21 H19 Br O6'
_chemical_formula_sum            'C21 H19 Br O6'
_chemical_formula_weight         447.27
_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
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-06-01
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2022-02-20 deposited with the CCDC.	2022-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                98.172(17)
_cell_angle_beta                 100.703(11)
_cell_angle_gamma                94.856(16)
_cell_formula_units_Z            2
_cell_length_a                   7.6456(9)
_cell_length_b                   8.944(3)
_cell_length_c                   13.8908(19)
_cell_measurement_reflns_used    747
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.6030
_cell_measurement_theta_min      3.6990
_cell_volume                     917.8(4)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   -2.00   24.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  120.0000 13

  2 omega  -32.00   10.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055   57.0000  -30.0000 21

  3 omega   -6.00   24.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000  -90.0000 15

  4 omega   -1.00   91.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  150.0000 46

  5 omega  -30.00   46.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000 -150.0000 38

  6 omega  -48.00   46.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000    0.0000 47

  7 omega  -48.00  -22.00   2.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -77.0000  120.0000 13
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0084001000
_diffrn_orient_matrix_UB_12      -0.0788143000
_diffrn_orient_matrix_UB_13      -0.0029846000
_diffrn_orient_matrix_UB_21      0.0003019000
_diffrn_orient_matrix_UB_22      0.0053599000
_diffrn_orient_matrix_UB_23      0.0514705000
_diffrn_orient_matrix_UB_31      -0.0946633000
_diffrn_orient_matrix_UB_32      -0.0162203000
_diffrn_orient_matrix_UB_33      -0.0106993000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.1274
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5735
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.37
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.277
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.872
_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_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3599
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1389
_refine_ls_R_factor_gt           0.0698
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0495P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1670
_reflns_number_gt                1957
_reflns_number_total             3599
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc02221d2.cif
_cod_data_source_block           wangxh_0531
_cod_original_cell_volume        917.9(3)
_cod_database_code               7130173
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C2(H2), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C10(H10A,H10B), C14(H14A,H14B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_olex2_date_sample_data_collection 2017-06-01
_olex2_submission_special_instructions 'No special instructions were received'