B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-catalyzed Markovnikov addition of indoles to aryl alkynes: an approach toward bis(indolyl)alkanes.
Ling, Fei; Xiao, Lian; Fang, Lu; Feng, Cong; Xie, Zhen; Lv, Yaping; Zhong, Weihui; Organic & biomolecular chemistry 16 (2018) 9274–9278; doi:10.1039/c8ob02805b

data_7156581
_publ_section_title
;
 B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-catalyzed Markovnikov addition
 of indoles to aryl alkynes: an approach toward bis(indolyl)alkanes.
;
_journal_issue                   47
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9274
_journal_page_last               9278
_journal_paper_doi               10.1039/c8ob02805b
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         '0.13(C24 H19 Cl N2)'
_chemical_formula_sum            'C H Cl N'
_chemical_formula_weight         62.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-07 deposited with the CCDC.
2018-11-21 downloaded from the CCDC.
;
_cell_angle_alpha                76.703(4)
_cell_angle_beta                 79.086(4)
_cell_angle_gamma                80.640(4)
_cell_formula_units_Z            31
_cell_length_a                   10.4828(5)
_cell_length_b                   13.6099(6)
_cell_length_c                   13.9679(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1889.45(15)
_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_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.866
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30140
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.501
_diffrn_reflns_theta_min         3.159
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.164
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_F_000             961
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         9108
_refine_ls_number_restraints     0
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_refine_ls_R_factor_all          0.0868
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0543P)^2^+0.3520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1329
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5922
_reflns_number_total             9108
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob02805b2.cif
_cod_data_source_block           temp-1
_cod_depositor_comments          'Adding full bibliography for 7156581.cif.'
_cod_database_code               7156581
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N003(H003), N004(H004), N005(H005), N006(H006), C00K(H00K), C00M(H00M),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00T(H00T), C00U(H00U), C00V(H00V),
 C00W(H00W), C00Y(H00Y), C00Z(H00Z), C010(H010), C013(H013), C014(H014),
 C015(H015), C016(H016), C017(H017), C018(H018), C019(H019), C01A(H01A),
 C01B(H01B), C01C(H01C), C01D(H01D), C01E(H01E), C01F(H01F), C01G(H01G),
 C01H(H01H), C01I(H01I)
2.b Idealised Me refined as rotating group:
 C00R(H00D,H00E,H00F), C00S(H00A,H00B,H00C)
;
_shelx_res_checksum              68794
_olex2_submission_special_instructions 'No special instructions were received'