Cupraelectro-Catalyzed Alkyne Annulation: Evidence for Distinct C–H Alkynylation and Decarboxylative C–H/C–C Manifolds
Tian, Cong; Dhawa, Uttam; Scheremetjew, Alexej; Ackermann, Lutz; ACS Catalysis 9 (2019) 7690–; doi:10.1021/acscatal.9b02348

data_4514820
_publ_section_title
;
 Cupraelectro-Catalyzed Alkyne Annulation: Evidence for Distinct C--H
 Alkynylation and Decarboxylative C--H/C--C Manifolds
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              7690
_journal_paper_doi               10.1021/acscatal.9b02348
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C25 H15 N3 O'
_chemical_formula_sum            'C25 H15 N3 O'
_chemical_formula_weight         373.40
_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_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.656(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   39.582(3)
_cell_length_b                   6.6842(5)
_cell_length_c                   13.9095(8)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    99.95
_cell_measurement_theta_max      29.569
_cell_measurement_theta_min      2.957
_cell_volume                     3647.3(4)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      99.95
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_h_min       -54
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31821
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.564
_diffrn_reflns_theta_min         2.955
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.8749
_exptl_absorpt_correction_T_min  0.8351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1605 before and 0.0559 after correction. The Ratio of minimum to maximum transmission is 0.9545. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       plate
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.379
_exptl_crystal_size_mid          0.351
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         5081
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0500P)^2^+3.4586P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1090
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4441
_reflns_number_total             5081
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b02348_si_002.cif
_cod_data_source_block           0593_cg_0m
_cod_original_cell_volume        3647.2(4)
_cod_database_code               4514820
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.968
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_shelx_res_checksum              4647
_shelx_hkl_checksum              32936
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 800'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_special_instructions 'No special instructions were received'