B(C6F5)3-mediated direct intramolecular C7-alkenylation of N-propargylindoles
Cui, Jie; Wang, Tongdao; Chemical Communications  (2023) –; doi:10.1039/D3CC02599C

data_7131947
_publ_section_title
;
 B(C6F5)3-mediated direct intramolecular C7-alkenylation of
 N-propargylindoles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC02599C
_journal_year                    2023
_chemical_formula_moiety         '0.926(C H2 Cl2), C31 H13 B F15 N'
_chemical_formula_sum            'C31.926 H14.852 B Cl1.852 F15 N'
_chemical_formula_weight         774.000
_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_Int_Tables_number      2
_audit_creation_date             2023-06-18
_audit_creation_method
;
Olex2 1.5-dev
(compiled 2023.04.26 svn.r751481ca for OlexSys, GUI svn.r6697)
;
_audit_update_record
;
2023-07-09 deposited with the CCDC.	2023-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                63.668(5)
_cell_angle_beta                 76.190(5)
_cell_angle_gamma                80.226(5)
_cell_formula_units_Z            2
_cell_length_a                   11.3290(19)
_cell_length_b                   11.9454(19)
_cell_length_c                   12.742(2)
_cell_measurement_reflns_used    8025
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      25.22
_cell_measurement_theta_min      2.39
_cell_volume                     1496.7(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-dev (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120.00
_diffrn_measured_fraction_theta_full 0.9954
_diffrn_measured_fraction_theta_max 0.9876
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.9954
_diffrn_reflns_Laue_measured_fraction_max 0.9876
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26644
_diffrn_reflns_point_group_measured_fraction_full 0.9954
_diffrn_reflns_point_group_measured_fraction_max 0.9876
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_T_max  0.5624
_exptl_absorpt_correction_T_min  0.5180
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0815 before and 0.0608 after correction. The Ratio of minimum to maximum transmission is 0.9211. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_description       block
_exptl_crystal_F_000             771.209
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.5975
_refine_diff_density_min         -0.4694
_refine_diff_density_rms         0.1007
_refine_ls_d_res_high            0.7963
_refine_ls_d_res_low             11.2230
_refine_ls_extinction_coef       0.0086(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0401
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    21
_refine_ls_number_parameters     472
_refine_ls_number_reflns         6120
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0401
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          -0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0766P)^2^+0.0901P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1375
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -13
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                4294
_reflns_number_total             6120
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3cc02599c2.cif
_cod_data_source_block           123456q
_cod_original_cell_volume        1496.8(4)
_cod_database_code               7131947
_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. Others
 Sof(Cl2)=Sof(Cl1)=Sof(C14)=Sof(H14a)=Sof(H14b)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C14(H14a,H14b)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C5(H5)
3.c Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C13(H13a,H13b,H13c)
;
_olex2_submission_special_instructions 'No special instructions were received'