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_7126140
_publ_section_title
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 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         'C42 H58 N4'
_chemical_formula_sum            'C42 H58 N4'
_chemical_formula_weight         618.96
_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             2019-10-31
_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                85.979(13)
_cell_angle_beta                 84.125(13)
_cell_angle_gamma                82.722(16)
_cell_formula_units_Z            1
_cell_length_a                   6.449(3)
_cell_length_b                   10.347(6)
_cell_length_c                   13.623(8)
_cell_measurement_reflns_used    1458
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      23.05
_cell_measurement_theta_min      2.42
_cell_volume                     895.5(8)
_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 0.9961
_diffrn_measured_fraction_theta_max 0.9961
_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  0.1470
_diffrn_reflns_av_unetI/netI     0.1464
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11757
_diffrn_reflns_theta_full        25.4038
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         1.99
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1083 before and 0.0508 after correction.
The Ratio of minimum to maximum transmission is 0.9265.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.1476
_exptl_crystal_description       block
_exptl_crystal_F_000             338.1138
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.3664
_refine_diff_density_min         -0.3911
_refine_diff_density_rms         0.1012
_refine_ls_d_res_high            0.8284
_refine_ls_d_res_low             10.2467
_refine_ls_goodness_of_fit_ref   0.8225
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    44
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.8225
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0462
_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^)+(0.0097P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0977
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                1772
_reflns_number_total             3290
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9cc08654d2.cif
_cod_data_source_block           final2_a
_cod_original_cell_volume        895.6(8)
_cod_database_code               7126140
_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:
 C04(H04), C05(H05), C101(H101), C102(H102), C104(H104), C201(H201),
 C202(H202), C204(H204)
2.b Idealised Me refined as rotating group:
 C02(H02a,H02b,H02c), C12(H12a,H12b,H12c), C13(H13a,H13b,H13c), C14(H14a,H14b,
 H14c), C22(H22a,H22b,H22c), C23(H23a,H23b,H23c), C24(H24a,H24b,H24c)
;
_olex2_submission_special_instructions 'No special instructions were received'