Frustrated Lewis pair-catalyzed double hydroarylation of alkynes with N-substituted pyrroles.
Guo, Jing; Cheong, Odelia; Bamford, Karlee L.; Zhou, Jiliang; Stephan, Douglas W.; Chemical communications (Cambridge, England) 56 (2020) 1855–1858; doi:10.1039/c9cc08654d

data_7126141
_publ_section_title
;
 Frustrated Lewis pair-catalyzed double hydroarylation of alkynes with
 N-substituted pyrroles.
;
_journal_issue                   12
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1855
_journal_page_last               1858
_journal_paper_doi               10.1039/c9cc08654d
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C24 H31 Br N2'
_chemical_formula_sum            'C24 H31 Br N2'
_chemical_formula_weight         427.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_audit_creation_date             2019-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-11-05 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.24(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.782(5)
_cell_length_b                   13.431(6)
_cell_length_c                   15.604(8)
_cell_measurement_reflns_used    8686
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      22.33
_cell_measurement_theta_min      2.45
_cell_volume                     2241.6(19)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9976
_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  0.0773
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            38958
_diffrn_reflns_theta_full        26.3716
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.844
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1082 before and 0.0720 after correction.
The Ratio of minimum to maximum transmission is 0.7729.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2665
_exptl_crystal_description       Shard
_exptl_crystal_F_000             895.1588
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.7676
_refine_diff_density_min         -0.8208
_refine_diff_density_rms         0.1060
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             9.3688
_refine_ls_goodness_of_fit_ref   1.0363
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     251
_refine_ls_number_reflns         4575
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0363
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0719P)^2^+1.3542P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1429
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -13
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              -9
_reflns_number_gt                3104
_reflns_number_total             4575
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9cc08654d2.cif
_cod_data_source_block           FINAL_a
_cod_depositor_comments
;

2025-03-30
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C48 H62 Br2 N4'
_cod_original_formula_weight         854.86
_cod_original_formula_moiety         '2(C24 H31 Br N2)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        2241.6(18)
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7126141
_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.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C20(H20), C12(H12), C9(H9), C11(H11), C24(H24), C21(H21), C3(H3),
 C4(H4), C23(H23)
2.b Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c), C15(H15a,H15b,H15c), C7(H7a,H7b,H7c), C8(H8a,H8b,H8c),
 C6(H6a,H6b,H6c), C14(H14a,H14b,H14c), C16(H16a,H16b,H16c)
;
_olex2_submission_special_instructions 'No special instructions were received'