Regioselective Cycloaddition of Potassium Alkynyltrifluoroborates with 3-Azetidinones and 3-Oxetanone by Nickel-Catalysed C‒C Bond Activation
Elwrfalli, Fathi; Esvan, Yannick J.; Robertson, Craig M.; Aissa, Christophe; Chemical Communications  (2018) –; doi:10.1039/C8CC09241A

data_7122717
_publ_section_title
;
 Regioselective Cycloaddition of Potassium Alkynyltrifluoroborates with
 3-Azetidinones and 3-Oxetanone by Nickel-Catalysed C--C Bond Activation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC09241A
_journal_year                    2018
_chemical_formula_moiety         'C13 H18 B F3 K N O3'
_chemical_formula_sum            'C13 H18 B F3 K N O3'
_chemical_formula_weight         343.19
_chemical_melting_point          429.0(10)
_chemical_name_systematic
'tert-butyl 5-butyl-3-oxo-4-(trifluoro-l4-boraneyl)-3,6-dihydropyridine-1(2H)-carboxylate, potassium salt'
_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     dual
_audit_creation_date             2018-10-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-20 deposited with the CCDC.
2018-12-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.096(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.296(3)
_cell_length_b                   5.8346(10)
_cell_length_c                   21.585(4)
_cell_measurement_reflns_used    4980
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      2.76
_cell_volume                     1630.9(6)
_computing_cell_refinement       'SAINT V8.30C (?, 2016)'
_computing_data_reduction        'SAINT V8.30C (?, 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      150
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0983
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            18485
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.612
_diffrn_reflns_theta_min         2.759
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.365
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1337 before and 0.0783 after correction. The Ratio of minimum to maximum transmission is 0.7768. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3340
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0460
_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^)+(0.0854P)^2^+0.3190P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1513
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2397
_reflns_number_total             3340
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc09241a2.cif
_cod_data_source_block           final
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '428-430' was changed to '429.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        1630.9(5)
_cod_database_code               7122717
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  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), C5(H5A,H5B)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C12(H12A,H12B,H12C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              88699
_shelx_hkl_checksum              47810
_olex2_submission_special_instructions 'No special instructions were received'