#------------------------------------------------------------------------------
#$Date: 2024-03-04 04:11:44 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290048 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/11/1571105.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1571105
loop_
_publ_author_name
'Prysiazhniuk, Kateryna'
'Polishchuk, Oleksandr'
'Shulha, Stanislav'
'Gudzikevych, Kyrylo'
'Datsenko, Oleksandr P.'
'Kubyshkin, Vladimir'
'Mykhailiuk, Pavel K.'
_publ_section_title
;
 Borylated cyclobutanes via 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         'C16 H27 B O3'
_chemical_formula_sum            'C16 H27 B O3'
_chemical_formula_weight         278.18
_chemical_melting_point          326
_chemical_name_systematic
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[3.6]decan-1-one
_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             2022-10-26
_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                102.908(3)
_cell_angle_beta                 102.707(3)
_cell_angle_gamma                103.170(3)
_cell_formula_units_Z            2
_cell_length_a                   6.7371(3)
_cell_length_b                   9.7392(5)
_cell_length_c                   13.4409(6)
_cell_measurement_reflns_used    2984
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.14
_cell_measurement_theta_min      2.24
_cell_volume                     802.20(7)
_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      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11109
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.243
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2822
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0431
_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/[σ²(Fo²)+(0.0408P)²+0.2336P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2207
_reflns_number_total             2822
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc06600b2.cif
_cod_data_source_block           vd49
_cod_database_code               1571105
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.985
_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.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B),
 C10(H10A,H10B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7690(2) 0.99252(14) 0.20251(12) 0.0622(4) Uani 1 1 d . . . . .
O2 O 0.30286(17) 0.49730(11) 0.20293(9) 0.0357(3) Uani 1 1 d . . . . .
O3 O 0.50959(16) 0.35719(11) 0.14957(9) 0.0345(3) Uani 1 1 d . . . . .
C1 C 0.6989(3) 0.86360(18) 0.19281(14) 0.0352(4) Uani 1 1 d . . . . .
C2 C 0.5075(3) 0.74399(17) 0.11629(14) 0.0359(4) Uani 1 1 d . . . . .
H2A H 0.486763 0.743271 0.040913 0.043 Uiso 1 1 calc R U . . .
H2B H 0.374283 0.740142 0.136695 0.043 Uiso 1 1 calc R U . . .
C3 C 0.6188(2) 0.62939(16) 0.14749(12) 0.0291(4) Uani 1 1 d . . . . .
H3 H 0.689521 0.595187 0.092588 0.035 Uiso 1 1 calc R U . . .
C4 C 0.7882(2) 0.75752(16) 0.24470(12) 0.0282(4) Uani 1 1 d . . . . .
C5 C 0.7393(2) 0.76751(18) 0.35167(13) 0.0343(4) Uani 1 1 d . . . . .
H5A H 0.793202 0.871762 0.395446 0.041 Uiso 1 1 calc R U . . .
H5B H 0.582957 0.736501 0.338335 0.041 Uiso 1 1 calc R U . . .
C6 C 0.8341(3) 0.67460(19) 0.41568(13) 0.0382(4) Uani 1 1 d . . . . .
H6A H 0.839647 0.584938 0.365607 0.046 Uiso 1 1 calc R U . . .
H6B H 0.739122 0.642972 0.458154 0.046 Uiso 1 1 calc R U . . .
C7 C 1.0576(3) 0.7558(2) 0.49066(14) 0.0458(5) Uani 1 1 d . . . . .
H7A H 1.053051 0.849271 0.536468 0.055 Uiso 1 1 calc R U . . .
H7B H 1.096766 0.695264 0.537687 0.055 Uiso 1 1 calc R U . . .
C8 C 1.2324(3) 0.7910(2) 0.43711(14) 0.0441(5) Uani 1 1 d . . . . .
H8A H 1.258935 0.697595 0.404705 0.053 Uiso 1 1 calc R U . . .
H8B H 1.364522 0.853240 0.492930 0.053 Uiso 1 1 calc R U . . .
C9 C 1.1899(3) 0.86895(19) 0.35128(14) 0.0375(4) Uani 1 1 d . . . . .
H9A H 1.324169 0.905772 0.334191 0.045 Uiso 1 1 calc R U . . .
H9B H 1.143012 0.955090 0.379686 0.045 Uiso 1 1 calc R U . . .
C10 C 1.0210(2) 0.76922(18) 0.24898(13) 0.0323(4) Uani 1 1 d . . . . .
H10A H 1.037626 0.668939 0.237252 0.039 Uiso 1 1 calc R U . . .
H10B H 1.050802 0.804931 0.188832 0.039 Uiso 1 1 calc R U . . .
C11 C 0.1845(2) 0.34515(17) 0.19088(13) 0.0326(4) Uani 1 1 d . . . . .
C12 C 0.3574(2) 0.26311(17) 0.18737(13) 0.0336(4) Uani 1 1 d . . . . .
C13 C 0.0070(3) 0.2966(2) 0.08716(16) 0.0491(5) Uani 1 1 d . . . . .
H13A H -0.079026 0.365354 0.089367 0.074 Uiso 1 1 calc R U . . .
H13B H -0.083067 0.197507 0.077733 0.074 Uiso 1 1 calc R U . . .
H13C H 0.068647 0.295674 0.027510 0.074 Uiso 1 1 calc R U . . .
C14 C 0.0908(3) 0.3442(2) 0.28340(16) 0.0496(5) Uani 1 1 d . . . . .
H14A H 0.202885 0.395757 0.350467 0.074 Uiso 1 1 calc R U . . .
H14B H 0.029317 0.242310 0.282270 0.074 Uiso 1 1 calc R U . . .
H14C H -0.020457 0.394068 0.277352 0.074 Uiso 1 1 calc R U . . .
C15 C 0.2803(3) 0.10918(18) 0.11031(16) 0.0476(5) Uani 1 1 d . . . . .
H15A H 0.220962 0.113909 0.038153 0.071 Uiso 1 1 calc R U . . .
H15B H 0.170339 0.046795 0.131253 0.071 Uiso 1 1 calc R U . . .
H15C H 0.399915 0.067462 0.111777 0.071 Uiso 1 1 calc R U . . .
C16 C 0.4783(3) 0.2600(2) 0.29625(16) 0.0522(5) Uani 1 1 d . . . . .
H16A H 0.600936 0.224171 0.290169 0.078 Uiso 1 1 calc R U . . .
H16B H 0.384203 0.194347 0.323110 0.078 Uiso 1 1 calc R U . . .
H16C H 0.527541 0.359644 0.345634 0.078 Uiso 1 1 calc R U . . .
B1 B 0.4766(3) 0.4923(2) 0.16799(14) 0.0281(4) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 O2 C11 107.39(12) . . ?
B1 O3 C12 107.72(12) . . ?
O1 C1 C2 133.38(16) . . ?
O1 C1 C4 132.34(16) . . ?
C2 C1 C4 93.87(12) . . ?
C1 C2 H2A 114.0 . . ?
C1 C2 H2B 114.0 . . ?
C1 C2 C3 87.93(12) . . ?
H2A C2 H2B 111.2 . . ?
C3 C2 H2A 114.0 . . ?
C3 C2 H2B 114.0 . . ?
C2 C3 H3 109.6 . . ?
C2 C3 C4 89.45(11) . . ?
C2 C3 B1 116.87(13) . . ?
C4 C3 H3 109.6 . . ?
B1 C3 H3 109.6 . . ?
B1 C3 C4 120.24(13) . . ?
C1 C4 C3 86.09(11) . . ?
C1 C4 C5 109.71(13) . . ?
C1 C4 C10 114.37(13) . . ?
C5 C4 C3 114.11(12) . . ?
C5 C4 C10 114.64(13) . . ?
C10 C4 C3 114.65(12) . . ?
C4 C5 H5A 108.5 . . ?
C4 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C6 C5 C4 114.96(13) . . ?
C6 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
C5 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C5 C6 C7 113.55(14) . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C6 C7 H7A 108.3 . . ?
C6 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C8 C7 C6 115.84(14) . . ?
C8 C7 H7A 108.3 . . ?
C8 C7 H7B 108.3 . . ?
C7 C8 H8A 108.2 . . ?
C7 C8 H8B 108.2 . . ?
C7 C8 C9 116.43(15) . . ?
H8A C8 H8B 107.3 . . ?
C9 C8 H8A 108.2 . . ?
C9 C8 H8B 108.2 . . ?
C8 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C8 C9 C10 113.06(14) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C4 C10 H10A 108.1 . . ?
C4 C10 H10B 108.1 . . ?
C9 C10 C4 116.90(13) . . ?
C9 C10 H10A 108.1 . . ?
C9 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
O2 C11 C12 102.60(11) . . ?
O2 C11 C13 106.25(13) . . ?
O2 C11 C14 108.56(13) . . ?
C13 C11 C12 113.65(14) . . ?
C14 C11 C12 115.14(14) . . ?
C14 C11 C13 109.89(15) . . ?
O3 C12 C11 102.35(12) . . ?
O3 C12 C15 108.39(13) . . ?
O3 C12 C16 106.67(13) . . ?
C15 C12 C11 115.13(13) . . ?
C15 C12 C16 109.84(15) . . ?
C16 C12 C11 113.74(15) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 B1 O3 113.55(14) . . ?
O2 B1 C3 122.41(15) . . ?
O3 B1 C3 124.01(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2025(19) . ?
O2 C11 1.4682(18) . ?
O2 B1 1.360(2) . ?
O3 C12 1.4691(18) . ?
O3 B1 1.361(2) . ?
C1 C2 1.508(2) . ?
C1 C4 1.529(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.560(2) . ?
C3 H3 1.0000 . ?
C3 C4 1.592(2) . ?
C3 B1 1.573(2) . ?
C4 C5 1.532(2) . ?
C4 C10 1.533(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.529(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.530(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.523(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.528(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.530(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.559(2) . ?
C11 C13 1.520(2) . ?
C11 C14 1.514(2) . ?
C12 C15 1.518(2) . ?
C12 C16 1.520(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 160.3(2) . . . . ?
O1 C1 C4 C3 -160.7(2) . . . . ?
O1 C1 C4 C5 85.1(2) . . . . ?
O1 C1 C4 C10 -45.3(3) . . . . ?
O2 C11 C12 O3 -24.64(14) . . . . ?
O2 C11 C12 C15 -141.99(14) . . . . ?
O2 C11 C12 C16 90.00(15) . . . . ?
C1 C2 C3 C4 12.13(12) . . . . ?
C1 C2 C3 B1 136.18(14) . . . . ?
C1 C4 C5 C6 -175.83(13) . . . . ?
C1 C4 C10 C9 94.46(17) . . . . ?
C2 C1 C4 C3 12.44(12) . . . . ?
C2 C1 C4 C5 -101.79(14) . . . . ?
C2 C1 C4 C10 127.78(14) . . . . ?
C2 C3 C4 C1 -11.99(12) . . . . ?
C2 C3 C4 C5 97.87(14) . . . . ?
C2 C3 C4 C10 -127.06(14) . . . . ?
C2 C3 B1 O2 -28.0(2) . . . . ?
C2 C3 B1 O3 149.75(15) . . . . ?
C3 C4 C5 C6 89.53(16) . . . . ?
C3 C4 C10 C9 -168.33(13) . . . . ?
C4 C1 C2 C3 -12.67(12) . . . . ?
C4 C3 B1 O2 78.5(2) . . . . ?
C4 C3 B1 O3 -103.81(18) . . . . ?
C4 C5 C6 C7 89.44(18) . . . . ?
C5 C4 C10 C9 -33.49(19) . . . . ?
C5 C6 C7 C8 -67.9(2) . . . . ?
C6 C7 C8 C9 51.3(2) . . . . ?
C7 C8 C9 C10 -71.3(2) . . . . ?
C8 C9 C10 C4 85.71(18) . . . . ?
C10 C4 C5 C6 -45.55(18) . . . . ?
C11 O2 B1 O3 -10.05(18) . . . . ?
C11 O2 B1 C3 167.90(14) . . . . ?
C12 O3 B1 O2 -7.16(18) . . . . ?
C12 O3 B1 C3 174.93(14) . . . . ?
C13 C11 C12 O3 89.62(15) . . . . ?
C13 C11 C12 C15 -27.7(2) . . . . ?
C13 C11 C12 C16 -155.73(14) . . . . ?
C14 C11 C12 O3 -142.36(13) . . . . ?
C14 C11 C12 C15 100.29(17) . . . . ?
C14 C11 C12 C16 -27.72(19) . . . . ?
B1 O2 C11 C12 21.51(16) . . . . ?
B1 O2 C11 C13 -98.05(15) . . . . ?
B1 O2 C11 C14 143.80(15) . . . . ?
B1 O3 C12 C11 19.84(15) . . . . ?
B1 O3 C12 C15 141.90(14) . . . . ?
B1 O3 C12 C16 -99.88(16) . . . . ?
B1 C3 C4 C1 -133.16(15) . . . . ?
B1 C3 C4 C5 -23.3(2) . . . . ?
B1 C3 C4 C10 111.77(16) . . . . ?
