Selectfluor facilitated bridging of indoles to bis(indolyl)methanes using methyl <i>tert</i>-butyl ether as a new methylene precursor.
Jin, Jiang; Li, Yinghua; Xiang, Shiqun; Fan, Weibin; Guo, Shiwei; Huang, Deguang; Organic & biomolecular chemistry 19 (2021) 4076–4081; doi:10.1039/d1ob00120e

data_7158012
_publ_section_title
;
 Selectfluor facilitated bridging of indoles to bis(indolyl)methanes using
 methyl <i>tert</i>-butyl ether as a new methylene precursor.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4076
_journal_page_last               4081
_journal_paper_doi               10.1039/d1ob00120e
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C23 H22 Br2 O6'
_chemical_formula_sum            'C23 H22 Br2 O6'
_chemical_formula_weight         554.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-01-15 deposited with the CCDC.	2021-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.6128(9)
_cell_length_b                   12.3072(6)
_cell_length_c                   9.3607(5)
_cell_measurement_reflns_used    3013
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      71.5710
_cell_measurement_theta_min      5.9170
_cell_volume                     2259.47(19)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.5594
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6485
_diffrn_reflns_point_group_measured_fraction_full 0.731
_diffrn_reflns_point_group_measured_fraction_max 0.723
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.994
_diffrn_reflns_theta_min         4.241
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    4.869
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
; 
 Flack x determined using 730 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.06(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3101
_refine_ls_number_restraints     487
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0678P)^2^+0.9057P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.362
_reflns_Friedel_fraction_full    0.424
_reflns_Friedel_fraction_max     0.411
_reflns_number_gt                2867
_reflns_number_total             3101
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00120e2.cif
_cod_data_source_block           Compound5g
_cod_depositor_comments
'Adding full bibliography for 7158011--7158015.cif.'
_cod_database_code               7158012
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.443
_shelx_estimated_absorpt_t_max   0.642
_shelx_res_checksum              30642