Borylated cyclobutanes <i>via</i> thermal [2 + 2]-cycloaddition.
Prysiazhniuk, Kateryna; Polishchuk, Oleksandr; Shulha, Stanislav; Gudzikevych, Kyrylo; Datsenko, Oleksandr P.; Kubyshkin, Vladimir; Mykhailiuk, Pavel K.; Chemical science 15 (2024) 3249–3254; doi:10.1039/d3sc06600b

data_1571102
_publ_section_title
;
 Borylated cyclobutanes <i>via</i> thermal [2 + 2]-cycloaddition.
;
_journal_issue                   9
_journal_name_full               'Chemical science'
_journal_page_first              3249
_journal_page_last               3254
_journal_paper_doi               10.1039/d3sc06600b
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C14 H23 B O4'
_chemical_formula_sum            'C14 H23 B O4'
_chemical_formula_weight         266.13
_chemical_melting_point          354
_chemical_name_systematic
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-7-oxaspiro[3.5]nonan-1-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-27
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-12-04 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.661(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.847(4)
_cell_length_b                   6.213(2)
_cell_length_c                   11.060(3)
_cell_measurement_reflns_used    3980
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.33
_cell_volume                     717.7(4)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.996
_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_unetI/netI     0.0745
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2503
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.989
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_min         1.912
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details
;
 Flack x determined using 762 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2503
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.177
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0972
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2727
_refine_ls_wR_factor_ref         0.2817
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2183
_reflns_number_total             2503
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc06600b2.cif
_cod_data_source_block           v131
_cod_database_code               1571102
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.752(7)
 0.248(7)
2. 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
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C8(H8A,H8B), C2(H2A,H2B), C5(H5A,H5B), C7(H7A,H7B)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C12(H12A,H12B,H12C), C11(H11A,H11B,
 H11C)
;
_shelx_res_checksum              99646
_olex2_submission_special_instructions 'No special instructions were received'