Room-temperature C–H bond alkynylation by merging cobalt and photocatalysts
Mandal, Rajib; Barsu, Nagaraju; Garai, Bholanath; Das, Abir; Perekalin, Dmitry; Sundararaju, Basker; Chemical Communications  (2021) –; doi:10.1039/D1CC05263B

data_7129179
_publ_section_title
;
 Room-temperature C--H bond alkynylation by merging cobalt and
 photocatalysts
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05263B
_journal_year                    2021
_chemical_formula_moiety         'C31 H36 N2 O3'
_chemical_formula_sum            'C31 H36 N2 O3'
_chemical_formula_weight         484.62
_chemical_name_systematic        5AC
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-09-16 deposited with the CCDC.	2021-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                106.492(2)
_cell_angle_beta                 95.327(2)
_cell_angle_gamma                97.944(2)
_cell_formula_units_Z            2
_cell_length_a                   8.2757(6)
_cell_length_b                   12.3903(9)
_cell_length_c                   13.7007(10)
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    273
_cell_measurement_theta_max      28.317
_cell_measurement_theta_min      2.510
_cell_volume                     1321.16(17)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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  0.0460
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33836
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.340
_diffrn_reflns_theta_min         2.509
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1009 before and 0.0646 after correction. The Ratio of minimum to maximum transmission is 0.8647. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_preparation       'Cobalt cataluzed annulation'
_exptl_crystal_recrystallization_method
'Slow Evaporation in dichloromethane solvent'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         6569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0483
_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^)+(0.0347P)^2^+0.9323P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1179
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5179
_reflns_number_total             6569
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05263b2.cif
_cod_data_source_block           24auga_0m
_cod_database_code               7129179
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.985
_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:
 C24(H24A,H24B), C26(H26A,H26B), C25(H25A,H25B), C29(H29A,H29B), C28(H28A,
 H28B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C12(H12), C15(H15), C16(H16), C17(H17), C6(H6), C4(H4),
 C5(H5)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C31(H31A,H31B,H31C), C30(H30A,H30B,H30C), C22(H22A,H22B,
 H22C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              12722
_olex2_submission_original_sample_id BSRM-3890
_olex2_submission_special_instructions 'No special instructions were received'