Electrooxidative Allene Annulations by Mild Cobalt-Catalyzed C–H Activation
Meyer, Tjark H.; Oliveira, João C. A.; Sau, Samaresh Chandra; Ang, Nate W. J.; Ackermann, Lutz; ACS Catalysis 8 (2018) 9140–; doi:10.1021/acscatal.8b03066

data_4515536
_publ_section_title
;
 Electrooxidative Allene Annulations by Mild Cobalt-Catalyzed C--H
 Activation
;
_journal_issue                   10
_journal_name_full               'ACS Catalysis'
_journal_page_first              9140
_journal_paper_doi               10.1021/acscatal.8b03066
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C30 H27 N2 O4 P'
_chemical_formula_sum            'C30 H27 N2 O4 P'
_chemical_formula_weight         510.50
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.366(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.1480(8)
_cell_length_b                   10.6001(6)
_cell_length_c                   19.4764(12)
_cell_measurement_reflns_used    2844
_cell_measurement_temperature    149.94
_cell_measurement_theta_max      26.34
_cell_measurement_theta_min      2.55
_cell_volume                     2492.5(3)
_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      149.94
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0249
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            46944
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.612
_diffrn_reflns_theta_min         2.191
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.8019
_exptl_absorpt_correction_T_min  0.7282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0715 before and 0.0438 after correction. The Ratio of minimum to maximum transmission is 0.9081. 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       block
_exptl_crystal_F_000             1072
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of methanol and DCM  by slow evaporation'
_exptl_crystal_size_max          0.465
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.208
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         9096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0360
_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^)+(0.0520P)^2^+0.7788P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1049
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8250
_reflns_number_total             9096
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs8b03066_si_002.cif
_cod_data_source_block           mo_0346_cg_0m
_cod_database_code               4515536
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.933
_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:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C15(H15),
 C18(H18), C19(H19), C21(H21), C22(H22), C25(H25), C26(H26), C28(H28), C29(H29)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              64288
_shelx_hkl_checksum              83787
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 800'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'