<i>Syn</i>- <i>versus anti</i>-carbopalladation of alkynes with organoborons: access to indoles symmetrically and unsymmetrically substituted on their 2,3-positions.
Ghasemi, Mehran; Rahimi, Banafshe; Dehghan, Maryam; Bernoosha, Mohammad Hossein; Jafarpour, Farnaz; Chemical communications (Cambridge, England) 59 (2023) 6873–6876; doi:10.1039/d3cc01753b

data_7131617
_publ_section_title
;
 <i>Syn</i>- <i>versus anti</i>-carbopalladation of alkynes with
 organoborons: access to indoles symmetrically and unsymmetrically
 substituted on their 2,3-positions.
;
_journal_issue                   45
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6873
_journal_page_last               6876
_journal_paper_doi               10.1039/d3cc01753b
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C28 H22 Cl N'
_chemical_formula_sum            'C28 H22 Cl N'
_chemical_formula_weight         407.91
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-06-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-10-24 deposited with the CCDC.	2023-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.60(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2102(18)
_cell_length_b                   20.916(4)
_cell_length_c                   11.778(2)
_cell_measurement_reflns_used    15614
_cell_measurement_temperature    290
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      1.9
_cell_volume                     2214.3(8)
_computing_cell_refinement       'Automar software package (3.3a, 2015)'
_computing_data_collection       'MAR345 dtb Program (1.24-4, 2013)'
_computing_data_reduction        'Automar software package (3.3a, 2015)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'PLATON (2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      290
_diffrn_detector                 'image-plate detector'
_diffrn_detector_area_resol_mean 0.81
_diffrn_detector_type            MAR345-dtb
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'one-circle diffractometer'
_diffrn_measurement_device_type  MAR-345-dtb
_diffrn_measurement_method       'image-plate detector - phi oscillation'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0796
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15614
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.008
_diffrn_reflns_theta_min         1.947
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0084(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4293
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0675
_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^)+(0.0381P)^2^+0.8638P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1385
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3605
_reflns_number_total             4293
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc01753b2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7131617--7131619.cif.'
_cod_database_code               7131617
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.964
_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.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C14(H14), C16(H16), C19(H19), C27(H27), C28(H28), C31(H31),
 C33(H33), C35(H35), C41(H41), C44(H44), C45(H45), C48(H48), C49(H49), C53(H53),
  C56(H56)
2.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C)
;
_olex2_submission_special_instructions 'No special instructions were received'