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_1571101
_publ_section_title
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 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 H19 B O3 S'
_chemical_formula_sum            'C14 H19 B O3 S'
_chemical_formula_weight         278.16
_chemical_melting_point          339
_chemical_name_systematic
(2r,3r)-3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(thiophen-3-yl)cyclobutanone
_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             2023-12-22
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
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2023-12-22 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_cell_angle_alpha                102.121(9)
_cell_angle_beta                 90.881(11)
_cell_angle_gamma                90.055(10)
_cell_formula_units_Z            2
_cell_length_a                   6.1465(9)
_cell_length_b                   8.6888(12)
_cell_length_c                   14.071(2)
_cell_measurement_reflns_used    1049
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      20.95
_cell_measurement_theta_min      2.40
_cell_volume                     734.63(18)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0604
_diffrn_reflns_av_unetI/netI     0.0875
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8385
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.480
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2578
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.1543
_refine_ls_R_factor_gt           0.0706
_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^)+(0.0907P)^2^+0.1300P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1609
_refine_ls_wR_factor_ref         0.2018
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1258
_reflns_number_total             2578
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc06600b2.cif
_cod_data_source_block           vd289
_cod_database_code               1571101
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.974
_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. Restrained distances
 C5-C6A = C7A-C8A
 1.36 with sigma of 0.001
 C5-C6B = C7B-C8B
 1.36 with sigma of 0.001
 C5-C7A = C5-C7B
 1.42 with sigma of 0.001
 C6A-S1A = C8A-S1A
 1.71 with sigma of 0.001
 C6B-S1B = C8B-S1B
 1.71 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C7B) = Uanis(C6A)
Uanis(C6B) = Uanis(C7A)
Uanis(C8A) = Uanis(C8B)
Uanis(S1B) = Uanis(S1A)
4. Others
 Sof(S1B)=Sof(C6B)=Sof(H6B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(H8B)=1-FVAR(1)
 Sof(S1A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
5.c Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C7A(H7A), C8A(H8A), C6B(H6B), C7B(H7B), C8B(H8B)
5.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
;
_shelx_res_checksum              80623
_olex2_submission_special_instructions 'No special instructions were received'