Stereoselective Synthesis of Dihydrofuranoindoles via the Friedel-Crafts Alkylation/Annulation Cascade Process.
Dong, Xiaodi; Tang, Zhishun; Ye, Ling; Shi, Zhichuan; Zhao, Zhigang; Li, Xuefeng; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00444

data_4038730
_publ_section_title
;
 Stereoselective Synthesis of Dihydrofuranoindoles via the Friedel-Crafts
 Alkylation/Annulation Cascade Process.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00444
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H11 Br N2 O3'
_chemical_formula_sum            'C16 H11 Br N2 O3'
_chemical_formula_weight         359.18
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-10-25
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1688(3)
_cell_length_b                   8.8842(3)
_cell_length_c                   20.4503(5)
_cell_measurement_reflns_used    3045
_cell_measurement_temperature    293.73(18)
_cell_measurement_theta_max      71.1490
_cell_measurement_theta_min      4.3100
_cell_volume                     1484.14(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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_environment      air
_diffrn_ambient_temperature      293.73(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_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   -105.00 -17.00   1.00    1.00    --  -36.29 -38.00 120.00   88
  2  \w   -108.00  -7.00   1.00    1.00    --  -36.29 -19.00  30.00  101
  3  \w     33.00 100.00   1.00    1.00    --   36.29-143.00-167.00   67
  4  \w     36.00 128.00   1.00    2.27    --  106.21 -30.00  60.00   92
  5  \w     37.00 109.00   1.00    2.27    --  106.21 -94.00  90.00   72
  6  \w     37.00 119.00   1.00    2.27    --  106.21-127.00   1.00   82
  7  \w    100.00 176.00   1.00    2.27    --  106.21 111.00  60.00   76
  8  \w     36.00 128.00   1.00    2.27    --  106.21 -30.00 150.00   92
  9  \w    100.00 176.00   1.00    2.27    --  106.21 111.00  90.00   76
 10  \w     39.00 133.00   1.00    2.27    --  106.21 -77.00 150.00   94
 11  \w    -55.00  33.00   1.00    1.00    --  -36.29  38.00  60.00   88
 12  \w     20.00 104.00   1.00    1.00    --   36.29  57.00   0.00   84
 13  \w     20.00  51.00   1.00    1.00    --   36.29  57.00 -60.00   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1456966000
_diffrn_orient_matrix_UB_12      0.0201564000
_diffrn_orient_matrix_UB_13      -0.0470389000
_diffrn_orient_matrix_UB_21      0.1193146000
_diffrn_orient_matrix_UB_22      -0.0395558000
_diffrn_orient_matrix_UB_23      0.0557154000
_diffrn_orient_matrix_UB_31      -0.0105133000
_diffrn_orient_matrix_UB_32      -0.1676579000
_diffrn_orient_matrix_UB_33      -0.0188377000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7281
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.535
_diffrn_reflns_theta_min         4.324
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.909
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
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    1.607
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
;
 Flack x determined using 949 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0902P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1402
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                2625
_reflns_number_total             2829
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00444_si_001.cif
_cod_data_source_block           lxf-dxd-1025-01
_cod_original_cell_volume        1484.14(7)
_cod_database_code               4038730
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C007(H007), C00F(H00F)
2.b Aromatic/amide H refined with riding coordinates:
 N003(H003), C00B(H00B), C00C(H00C), C00G(H00G), C00H(H00H), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M)
;
_shelx_res_checksum              39453
_shelx_hkl_checksum              39775
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-10-25
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.404
_oxdiff_exptl_absorpt_empirical_full_min 0.558