Transient Protection of Strained Alkynes from Click Reaction via Complexation with Copper.
Yoshida, Suguru; Hatakeyama, Yasutomo; Johmoto, Kohei; Uekusa, Hidehiro; Hosoya, Takamitsu; Journal of the American Chemical Society 136 (2014) 13590–13593; doi:10.1021/ja507660x

data_4122639
_publ_section_title
;
 Transient Protection of Strained Alkynes from Click Reaction via
 Complexation with Copper.
;
_journal_issue                   39
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13590
_journal_page_last               13593
_journal_paper_doi               10.1021/ja507660x
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C18 H17 B Cu F4 N O'
_chemical_formula_weight         413.67
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 122.6590(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7109(2)
_cell_length_b                   18.3710(3)
_cell_length_c                   13.1898(2)
_cell_measurement_reflns_used    9218
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.21
_cell_measurement_theta_min      3.98
_cell_volume                     1777.02(6)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID II IP Area Detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20456
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         68.208
_diffrn_reflns_theta_min         4.653
_diffrn_source                   'rotating anode X-ray tube'
_exptl_absorpt_coefficient_mu    2.163
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chip
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.136
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0574P)^2^+0.5877P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1023
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2843
_reflns_number_total             3258
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja507660x_si_002.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 4122639.cif.'
_cod_database_code               4122639
_shelx_estimated_absorpt_t_min   0.757
_shelx_estimated_absorpt_t_max   0.938
_shelxl_version_number           2013-3
_shelx_res_checksum              29986
_shelx_hkl_checksum              13588