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_7130172
_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 H16 O6'
_chemical_formula_sum            'C21 H16 O6'
_chemical_formula_weight         364.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-11-10
_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                90.00
_cell_angle_beta                 106.8(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.52(17)
_cell_length_b                   8.28(2)
_cell_length_c                   17.87(11)
_cell_measurement_reflns_used    533
_cell_measurement_temperature    293.02(10)
_cell_measurement_theta_max      20.0800
_cell_measurement_theta_min      3.4750
_cell_volume                     1632(3)
_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      293.02(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
  1 omega  -11.00   22.00   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000    0.0000 22

  2 omega   -5.00   83.50   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000 -120.0000 59

  3 omega   -9.00   91.50   1.5000   16.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000  150.0000 67
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0160254000
_diffrn_orient_matrix_UB_12      -0.0025599000
_diffrn_orient_matrix_UB_13      -0.0363283000
_diffrn_orient_matrix_UB_21      -0.0609387000
_diffrn_orient_matrix_UB_22      0.0073659000
_diffrn_orient_matrix_UB_23      -0.0224708000
_diffrn_orient_matrix_UB_31      0.0058432000
_diffrn_orient_matrix_UB_32      0.0841701000
_diffrn_orient_matrix_UB_33      0.0008776000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.1175
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5663
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.42
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.981
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3177
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1794
_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
'calc w=1/[\s^2^(Fo^2^)+(0.0586P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1575
_refine_ls_wR_factor_ref         0.2213
_reflns_number_gt                1262
_reflns_number_total             3177
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc02221d2.cif
_cod_data_source_block           xiaoj_1108
_cod_original_cell_volume        1633(26)
_cod_database_code               7130172
_reflns_odcompleteness_completeness 97.83
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C20(H20A,H20B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_olex2_date_sample_data_collection 2017-11-10
_olex2_submission_special_instructions 'No special instructions were received'