Diastereoselective Construction of Spiro-furo[3,2- c]benzopyranoxindoles through a Cu(OTf)<sub>2</sub>/AcOH Cooperative Promoted Bicyclization Reaction.
Li, De-Feng; Gu, Yan; Zhang, Jing-Ru; Liu, Kun; Zhao, Li-Ming; The Journal of organic chemistry 84 (2019) 879–887; doi:10.1021/acs.joc.8b02762

data_4035965
_publ_section_title
;
 Diastereoselective Construction of Spiro-furo[3,2- c]benzopyranoxindoles
 through a Cu(OTf)<sub>2</sub>/AcOH Cooperative Promoted Bicyclization
 Reaction.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              879
_journal_page_last               887
_journal_paper_doi               10.1021/acs.joc.8b02762
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C25 H20 F N O3'
_chemical_formula_sum            'C25 H20 F N O3'
_chemical_formula_weight         401.42
_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     dual
_audit_creation_date             2018-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                102.175(10)
_cell_angle_beta                 92.846(11)
_cell_angle_gamma                98.990(11)
_cell_formula_units_Z            2
_cell_length_a                   8.6230(12)
_cell_length_b                   9.5904(12)
_cell_length_c                   12.8096(16)
_cell_measurement_reflns_used    1560
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.5840
_cell_measurement_theta_min      3.0020
_cell_volume                     1019.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     -1.00  82.00   1.00    7.50    --   15.34  57.00 -60.00   83
  2  \w     35.00  82.00   1.00    7.50    --   15.34 178.00-180.00   47
  3  \w    -38.00  50.00   1.00    7.50    --  -16.12  77.00   0.00   88
  4  \w    -21.00   6.00   1.00    7.50    --  -16.12  38.00 150.00   27
  5  \w      8.00  35.00   1.00    7.50    --  -16.12  38.00 150.00   27
  6  \w    -20.00  21.00   1.00    7.50    --  -16.12 -99.00  60.00   41
  7  \w    -51.00  42.00   1.00    7.50    --   15.34 -77.00-180.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0239662000
_diffrn_orient_matrix_UB_12      0.0587732000
_diffrn_orient_matrix_UB_13      -0.0244596000
_diffrn_orient_matrix_UB_21      -0.0033851000
_diffrn_orient_matrix_UB_22      -0.0490567000
_diffrn_orient_matrix_UB_23      -0.0502846000
_diffrn_orient_matrix_UB_31      -0.0800051000
_diffrn_orient_matrix_UB_32      0.0059804000
_diffrn_orient_matrix_UB_33      -0.0102823000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1018
_diffrn_reflns_av_unetI/netI     0.1484
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7942
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_min         2.785
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4285
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.917
_refine_ls_R_factor_all          0.1449
_refine_ls_R_factor_gt           0.0656
_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^)+(0.0630P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1982
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1809
_reflns_number_total             4285
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02762_si_002.cif
_cod_data_source_block           exp_5625
_cod_database_code               4035965
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.977
_reflns_odcompleteness_completeness 98.82
_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), C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14),
 C15(H15), C22(H22), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              76487
_shelx_hkl_checksum              55101
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 9.971
_oxdiff_exptl_absorpt_empirical_full_min 0.358