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

data_7131950
_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         'C31 H11 B F15 N, 0.5[CH2Cl2]'
_chemical_formula_sum            'C31.5 H12 B Cl F15 N'
_chemical_formula_weight         735.706
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_Int_Tables_number      15
_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
;
2023-07-28 deposited with the CCDC.	2023-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.360(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.3655(6)
_cell_length_b                   13.5543(6)
_cell_length_c                   20.8012(8)
_cell_measurement_reflns_used    9039
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      23.73
_cell_measurement_theta_min      2.62
_cell_volume                     5732.1(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      190.00
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_measured_fraction_theta_max 0.9981
_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  0.0876
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_Laue_measured_fraction_full 0.9985
_diffrn_reflns_Laue_measured_fraction_max 0.9981
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            39948
_diffrn_reflns_point_group_measured_fraction_full 0.9985
_diffrn_reflns_point_group_measured_fraction_max 0.9981
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.5629
_exptl_absorpt_correction_T_min  0.4857
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1286 before and 0.0803 after correction. The Ratio of minimum to maximum transmission is 0.8629. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_description       block
_exptl_crystal_F_000             2924.284
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.43
_refine_diff_density_max         0.3649
_refine_diff_density_min         -0.2944
_refine_diff_density_rms         0.0708
_refine_ls_d_res_high            0.8255
_refine_ls_d_res_low             7.7654
_refine_ls_extinction_coef       0.00114(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0371
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     436
_refine_ls_number_reflns         5324
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0371
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          -0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0373P)^2^+3.2776P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.1020
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              24
_reflns_limit_h_min              -24
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                3818
_reflns_number_total             5324
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3cc02599c2.cif
_cod_data_source_block           123456
_cod_original_formula_sum        'C31.5 H12 B1 Cl1 F15 N1'
_cod_database_code               7131950
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
3. Uiso/Uaniso restraints and constraints
: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C5(H5), C4(H4), C2(H2), C6(H6)
5.b Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C13(H13a,H13b,H13c)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 160 electrons were 
found in a volume of 664\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 0.5[CH2Cl2] per Formula Unit 
which account for 168 electrons per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'