Substituted cyclopropanols <i>via</i> sequential cyclopropanation and oxidative hydrolysis of vinylboronates.
Shuvakin, Serhii I.; Serhieiev, Oleksii M.; Dashko, Maksym O.; Pendiukh, Viacheslav V.; Ivonin, Sergey P.; Shishkina, Svitlana V.; Rozhenko, Alexander B.; Pashenko, Olexandr Ye; Volochnyuk, Dmytro M.; Ryabukhin, Serhiy V.; Organic & biomolecular chemistry 23 (2025) 6343–6348; doi:10.1039/d5ob00691k

data_7160565
_publ_section_title
;
 Substituted cyclopropanols <i>via</i> sequential cyclopropanation and
 oxidative hydrolysis of vinylboronates.
;
_journal_issue                   26
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6343
_journal_page_last               6348
_journal_paper_doi               10.1039/d5ob00691k
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C9 H8 Cl2 O'
_chemical_formula_sum            'C9 H8 Cl2 O'
_chemical_formula_weight         203.05
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-08
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-11-08 deposited with the CCDC.	2025-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            32
_cell_length_a                   31.0324(14)
_cell_length_b                   31.0324(14)
_cell_length_c                   7.7109(4)
_cell_measurement_reflns_used    4002
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.63
_cell_volume                     7425.7(6)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0563
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            66862
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         1.312
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_description       needle
_exptl_crystal_F_000             3328
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3271
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.1393
_refine_ls_R_factor_gt           0.0930
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+63.0160P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.1588
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2190
_reflns_number_total             3271
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00691k2.cif
_cod_data_source_block           10b
_cod_depositor_comments          'Adding full bibliography for 7160565.cif.'
_cod_original_cell_volume        7425.7(8)
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_database_code               7160565
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.882
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.93(7)
 0.07(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
3. Others
 Fixed Sof: H1A(0.5) H1AA(0.5) H1B(0.5) H1BA(0.5)
4.a Ternary CH refined with riding coordinates:
 C7A(H7A), C7B(H7B), C9A(H9A), C9B(H9B)
4.b Secondary CH2 refined with riding coordinates:
 C8A(H8AA,H8AB), C8B(H8BA,H8BB)
4.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C3B(H3B), C4A(H4A), C4B(H4B), C5A(H5A), C5B(H5B)
4.d Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1A(H1AA), O1B(H1B), O1B(H1BA)
;
_shelx_res_checksum              72063
_olex2_submission_special_instructions 'No special instructions were received'