# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_v129a
_database_code_depnum_ccdc_archive 'CCDC 2312007'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;Institute of Organic Chemistry of the National Academy of Sciences of Ukraine
Ukraine
;
_audit_update_record             
;
2023-12-04 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_audit_creation_date             2023-03-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
7,7-Difluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[3.5]nonan-1-one
_chemical_formula_moiety         'C15 H23 B F2 O3'
_chemical_formula_sum            'C15 H23 B F2 O3'
_chemical_formula_weight         300.14
_chemical_melting_point          353
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.3713(5)
_cell_length_b                   6.2669(3)
_cell_length_c                   18.6934(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.481(2)
_cell_angle_gamma                90
_cell_volume                     1565.92(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2991
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.52
_cell_measurement_theta_min      2.18
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            20344
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         1.896
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2063
_reflns_number_total             2764
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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)'
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2764
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0812
_refine_ls_restrained_S_all      1.159
_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)+(0.0405P)²+5.0180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1906
_refine_ls_wR_factor_ref         0.2000
_refine_special_details          ?
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B), C9(H9A,H9B)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
B1 B 0.5345(3) 0.7984(8) 0.6438(2) 0.0270(11) Uani 1 1 d . . . . .
C1 C 0.4391(3) 0.8962(7) 0.6796(2) 0.0304(10) Uani 1 1 d . . . . .
H1 H 0.436338 1.053320 0.670555 0.037 Uiso 1 1 calc R U . . .
C2 C 0.3339(3) 0.7949(8) 0.6632(2) 0.0367(11) Uani 1 1 d . . . . .
H2A H 0.288571 0.886629 0.633961 0.044 Uiso 1 1 calc R U . . .
H2B H 0.336655 0.648370 0.643547 0.044 Uiso 1 1 calc R U . . .
C3 C 0.3152(3) 0.8037(7) 0.7429(2) 0.0280(9) Uani 1 1 d . . . . .
C4 C 0.4259(3) 0.8513(7) 0.7618(2) 0.0262(9) Uani 1 1 d . . . . .
C5 C 0.4459(3) 1.0360(7) 0.8134(2) 0.0288(9) Uani 1 1 d . . . . .
H5A H 0.517547 1.075416 0.812246 0.035 Uiso 1 1 calc R U . . .
H5B H 0.406166 1.161530 0.797536 0.035 Uiso 1 1 calc R U . . .
C6 C 0.4191(3) 0.9788(8) 0.8896(2) 0.0354(11) Uani 1 1 d . . . . .
H6A H 0.440064 1.095996 0.922151 0.042 Uiso 1 1 calc R U . . .
H6B H 0.345672 0.962628 0.892366 0.042 Uiso 1 1 calc R U . . .
C7 C 0.4689(3) 0.7757(7) 0.9134(2) 0.0304(10) Uani 1 1 d . . . . .
C8 C 0.4521(3) 0.5910(7) 0.8648(2) 0.0316(10) Uani 1 1 d . . . . .
H8A H 0.380970 0.547462 0.865786 0.038 Uiso 1 1 calc R U . . .
H8B H 0.493467 0.468994 0.881581 0.038 Uiso 1 1 calc R U . . .
C9 C 0.4794(3) 0.6489(7) 0.7881(2) 0.0280(9) Uani 1 1 d . . . . .
H9A H 0.552595 0.670494 0.786038 0.034 Uiso 1 1 calc R U . . .
H9B H 0.461218 0.528873 0.755903 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6978(3) 0.7168(8) 0.6306(2) 0.0372(11) Uani 1 1 d . . . . .
C11 C 0.7221(4) 0.5405(9) 0.6851(2) 0.0490(13) Uani 1 1 d . . . . .
H11A H 0.770686 0.441409 0.665026 0.073 Uiso 1 1 calc R U . . .
H11B H 0.660762 0.462930 0.696140 0.073 Uiso 1 1 calc R U . . .
H11C H 0.750435 0.604259 0.728984 0.073 Uiso 1 1 calc R U . . .
C12 C 0.7912(3) 0.8347(9) 0.6121(3) 0.0456(13) Uani 1 1 d . . . . .
H12A H 0.825940 0.881254 0.656187 0.068 Uiso 1 1 calc R U . . .
H12B H 0.773632 0.959529 0.582823 0.068 Uiso 1 1 calc R U . . .
H12C H 0.835008 0.740309 0.585262 0.068 Uiso 1 1 calc R U . . .
C13 C 0.6343(3) 0.6298(8) 0.5660(2) 0.0379(11) Uani 1 1 d . . . . .
C14 C 0.6532(4) 0.3985(8) 0.5461(3) 0.0458(13) Uani 1 1 d . . . . .
H14A H 0.723545 0.380473 0.533870 0.069 Uiso 1 1 calc R U . . .
H14B H 0.610331 0.359444 0.504838 0.069 Uiso 1 1 calc R U . . .
H14C H 0.637938 0.306268 0.586721 0.069 Uiso 1 1 calc R U . . .
C15 C 0.6399(4) 0.7721(9) 0.4998(2) 0.0466(13) Uani 1 1 d . . . . .
H15A H 0.627613 0.920667 0.513358 0.070 Uiso 1 1 calc R U . . .
H15B H 0.589151 0.726736 0.464215 0.070 Uiso 1 1 calc R U . . .
H15C H 0.706441 0.760040 0.479433 0.070 Uiso 1 1 calc R U . . .
F1 F 0.4399(2) 0.7271(4) 0.98143(12) 0.0449(7) Uani 1 1 d . . . . .
F2 F 0.57103(18) 0.8109(5) 0.92136(13) 0.0447(7) Uani 1 1 d . . . . .
O1 O 0.2416(2) 0.7919(5) 0.77786(16) 0.0383(8) Uani 1 1 d . . . . .
O2 O 0.6283(2) 0.8636(5) 0.66353(15) 0.0396(8) Uani 1 1 d . . . . .
O3 O 0.5320(2) 0.6486(5) 0.59245(16) 0.0393(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
B1 C1 1.580(6) . ?
B1 O2 1.361(5) . ?
B1 O3 1.342(6) . ?
C1 H1 1.0000 . ?
C1 C2 1.566(6) . ?
C1 C4 1.575(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.519(6) . ?
C3 C4 1.542(5) . ?
C3 O1 1.197(5) . ?
C4 C5 1.526(6) . ?
C4 C9 1.531(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.521(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.499(6) . ?
C7 C8 1.484(6) . ?
C7 F1 1.373(5) . ?
C7 F2 1.388(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.533(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.533(7) . ?
C10 C12 1.498(6) . ?
C10 C13 1.556(6) . ?
C10 O2 1.455(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.519(7) . ?
C13 C15 1.529(6) . ?
C13 O3 1.472(5) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
O2 B1 C1 121.1(4) . . ?
O3 B1 C1 124.7(4) . . ?
O3 B1 O2 114.2(4) . . ?
B1 C1 H1 109.7 . . ?
C2 C1 B1 119.4(4) . . ?
C2 C1 H1 109.7 . . ?
C2 C1 C4 89.8(3) . . ?
C4 C1 B1 117.2(3) . . ?
C4 C1 H1 109.7 . . ?
C1 C2 H2A 114.0 . . ?
C1 C2 H2B 114.0 . . ?
H2A C2 H2B 111.2 . . ?
C3 C2 C1 87.9(3) . . ?
C3 C2 H2A 114.0 . . ?
C3 C2 H2B 114.0 . . ?
C2 C3 C4 92.8(3) . . ?
O1 C3 C2 133.8(4) . . ?
O1 C3 C4 133.3(4) . . ?
C3 C4 C1 86.8(3) . . ?
C5 C4 C1 117.3(4) . . ?
C5 C4 C3 116.3(3) . . ?
C5 C4 C9 110.6(3) . . ?
C9 C4 C1 113.5(3) . . ?
C9 C4 C3 110.5(3) . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 C4 111.8(4) . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 C5 111.4(4) . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C8 C7 C6 114.9(3) . . ?
F1 C7 C6 109.2(3) . . ?
F1 C7 C8 110.6(4) . . ?
F1 C7 F2 103.7(3) . . ?
F2 C7 C6 109.0(4) . . ?
F2 C7 C8 108.8(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 C9 110.6(4) . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C4 C9 C8 112.1(3) . . ?
C4 C9 H9A 109.2 . . ?
C4 C9 H9B 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C13 111.4(4) . . ?
C12 C10 C11 110.2(4) . . ?
C12 C10 C13 115.8(4) . . ?
O2 C10 C11 107.5(3) . . ?
O2 C10 C12 109.3(4) . . ?
O2 C10 C13 102.1(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C10 115.7(4) . . ?
C14 C13 C15 110.3(4) . . ?
C15 C13 C10 112.7(4) . . ?
O3 C13 C10 101.8(3) . . ?
O3 C13 C14 108.7(4) . . ?
O3 C13 C15 106.9(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
B1 O2 C10 106.8(3) . . ?
B1 O3 C13 106.9(3) . . ?

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
B1 C1 C2 C3 133.9(4) . . . . ?
B1 C1 C4 C3 -135.6(4) . . . . ?
B1 C1 C4 C5 106.4(4) . . . . ?
B1 C1 C4 C9 -24.6(5) . . . . ?
C1 B1 O2 C10 169.8(4) . . . . ?
C1 B1 O3 C13 170.7(4) . . . . ?
C1 C2 C3 C4 -12.8(3) . . . . ?
C1 C2 C3 O1 163.0(5) . . . . ?
C1 C4 C5 C6 173.5(3) . . . . ?
C1 C4 C9 C8 -171.2(3) . . . . ?
C2 C1 C4 C3 -12.3(3) . . . . ?
C2 C1 C4 C5 -130.3(4) . . . . ?
C2 C1 C4 C9 98.7(4) . . . . ?
C2 C3 C4 C1 12.7(3) . . . . ?
C2 C3 C4 C5 131.7(4) . . . . ?
C2 C3 C4 C9 -101.1(4) . . . . ?
C3 C4 C5 C6 73.0(4) . . . . ?
C3 C4 C9 C8 -75.7(4) . . . . ?
C4 C1 C2 C3 12.5(3) . . . . ?
C4 C5 C6 C7 52.8(5) . . . . ?
C5 C4 C9 C8 54.6(4) . . . . ?
C5 C6 C7 C8 -53.1(5) . . . . ?
C5 C6 C7 F1 -178.0(3) . . . . ?
C5 C6 C7 F2 69.3(4) . . . . ?
C6 C7 C8 C9 52.8(5) . . . . ?
C7 C8 C9 C4 -53.2(4) . . . . ?
C9 C4 C5 C6 -54.2(4) . . . . ?
C10 C13 O3 B1 23.0(5) . . . . ?
C11 C10 C13 C14 -31.3(5) . . . . ?
C11 C10 C13 C15 -159.5(4) . . . . ?
C11 C10 C13 O3 86.4(4) . . . . ?
C11 C10 O2 B1 -93.5(4) . . . . ?
C12 C10 C13 C14 95.7(5) . . . . ?
C12 C10 C13 C15 -32.5(6) . . . . ?
C12 C10 C13 O3 -146.7(4) . . . . ?
C12 C10 O2 B1 147.0(4) . . . . ?
C13 C10 O2 B1 23.9(4) . . . . ?
C14 C13 O3 B1 145.6(4) . . . . ?
C15 C13 O3 B1 -95.4(4) . . . . ?
F1 C7 C8 C9 177.1(3) . . . . ?
F2 C7 C8 C9 -69.6(4) . . . . ?
O1 C3 C4 C1 -163.1(5) . . . . ?
O1 C3 C4 C5 -44.2(7) . . . . ?
O1 C3 C4 C9 83.0(6) . . . . ?
O2 B1 C1 C2 -171.6(4) . . . . ?
O2 B1 C1 C4 -65.1(6) . . . . ?
O2 B1 O3 C13 -9.1(5) . . . . ?
O2 C10 C13 C14 -145.7(4) . . . . ?
O2 C10 C13 C15 86.1(4) . . . . ?
O2 C10 C13 O3 -28.1(4) . . . . ?
O3 B1 C1 C2 8.7(6) . . . . ?
O3 B1 C1 C4 115.2(5) . . . . ?
O3 B1 O2 C10 -10.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vd289
_database_code_depnum_ccdc_archive 'CCDC 2321392'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;Institute of Organic Chemistry of the National Academy of Sciences of Ukraine
Ukraine
;
_audit_update_record             
;
2023-12-22 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_audit_creation_date             2023-12-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
(2r,3r)-3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(thiophen-3-yl)cyclobutanone
_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
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1465(9)
_cell_length_b                   8.6888(12)
_cell_length_c                   14.071(2)
_cell_angle_alpha                102.121(9)
_cell_angle_beta                 90.881(11)
_cell_angle_gamma                90.055(10)
_cell_volume                     734.63(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1049
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      20.95
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_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       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1258
_reflns_number_total             2578
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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)'
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_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_R_factor_all          0.1543
_refine_ls_R_factor_gt           0.0706
_refine_ls_restrained_S_all      0.989
_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)+(0.0907P)²+0.1300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1609
_refine_ls_wR_factor_ref         0.2018
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.2169(5) 0.2333(4) 0.1924(2) 0.0917(12) Uani 1 1 d . . . . .
O2 O 0.9526(5) 0.6476(3) 0.2470(2) 0.0714(9) Uani 1 1 d . . . . .
O3 O 0.7230(4) 0.6795(3) 0.12521(19) 0.0596(8) Uani 1 1 d . . . . .
C1 C 0.3655(7) 0.3209(5) 0.1900(3) 0.0584(12) Uani 1 1 d . . . . .
C2 C 0.4947(7) 0.3625(5) 0.1110(3) 0.0704(13) Uani 1 1 d . . . . .
H2A H 0.428065 0.445220 0.081362 0.084 Uiso 1 1 calc R U . . .
H2B H 0.538418 0.270673 0.060600 0.084 Uiso 1 1 calc R U . . .
C3 C 0.6767(7) 0.4243(4) 0.1879(3) 0.0530(11) Uani 1 1 d . . . . .
H3 H 0.790674 0.342149 0.187569 0.064 Uiso 1 1 calc R U . . .
C4 C 0.5091(6) 0.4206(4) 0.2693(3) 0.0532(11) Uani 1 1 d . . . . .
H4 H 0.443477 0.527243 0.290828 0.064 Uiso 1 1 calc R U . . .
C5 C 0.5761(6) 0.3566(4) 0.3567(3) 0.0534(11) Uani 1 1 d D . . . .
C9 C 0.9822(7) 0.8104(5) 0.2365(3) 0.0581(12) Uani 1 1 d . . . . .
C10 C 0.8845(7) 0.8059(5) 0.1349(3) 0.0580(12) Uani 1 1 d . . . . .
C11 C 0.8542(9) 0.9130(6) 0.3161(3) 0.0883(16) Uani 1 1 d . . . . .
H11A H 0.699923 0.883833 0.308266 0.132 Uiso 1 1 calc R U . . .
H11B H 0.871676 1.023632 0.312107 0.132 Uiso 1 1 calc R U . . .
H11C H 0.907889 0.898317 0.379473 0.132 Uiso 1 1 calc R U . . .
C12 C 1.2210(7) 0.8505(5) 0.2490(3) 0.0745(14) Uani 1 1 d . . . . .
H12A H 1.265785 0.855709 0.316703 0.112 Uiso 1 1 calc R U . . .
H12B H 1.247218 0.952701 0.232013 0.112 Uiso 1 1 calc R U . . .
H12C H 1.305371 0.769298 0.206232 0.112 Uiso 1 1 calc R U . . .
C13 C 0.7682(7) 0.9526(5) 0.1218(4) 0.0771(15) Uani 1 1 d . . . . .
H13A H 0.702875 0.935049 0.056423 0.116 Uiso 1 1 calc R U . . .
H13B H 0.872228 1.040125 0.130174 0.116 Uiso 1 1 calc R U . . .
H13C H 0.653817 0.978078 0.170283 0.116 Uiso 1 1 calc R U . . .
C14 C 1.0481(8) 0.7558(6) 0.0539(3) 0.0839(16) Uani 1 1 d . . . . .
H14A H 1.120647 0.658917 0.062151 0.126 Uiso 1 1 calc R U . . .
H14B H 1.156804 0.839266 0.056707 0.126 Uiso 1 1 calc R U . . .
H14C H 0.972053 0.736881 -0.009245 0.126 Uiso 1 1 calc R U . . .
B1 B 0.7849(8) 0.5875(5) 0.1856(3) 0.0509(12) Uani 1 1 d . . . . .
S1A S 0.5690(5) 0.2249(4) 0.5029(2) 0.0855(9) Uani 0.619(3) 1 d D . P A 1
C6A C 0.4383(8) 0.2866(13) 0.4096(6) 0.064(2) Uani 0.619(3) 1 d D . P A 1
H6A H 0.286667 0.273563 0.396187 0.076 Uiso 0.619(3) 1 calc R U P A 1
C7A C 0.7790(10) 0.386(2) 0.4068(7) 0.065(3) Uani 0.619(3) 1 d D . P A 1
H7A H 0.887633 0.451394 0.388255 0.078 Uiso 0.619(3) 1 calc R U P A 1
C8A C 0.8071(13) 0.3145(15) 0.4833(9) 0.062(3) Uani 0.619(3) 1 d D . P A 1
H8A H 0.938165 0.314358 0.519931 0.074 Uiso 0.619(3) 1 calc R U P A 1
S1B S 0.7891(10) 0.2956(11) 0.4986(6) 0.0855(9) Uani 0.381(3) 1 d D . P A 2
C6B C 0.7838(11) 0.360(4) 0.3918(12) 0.065(3) Uani 0.381(3) 1 d D . P A 2
H6B H 0.907314 0.393439 0.361584 0.078 Uiso 0.381(3) 1 calc R U P A 2
C7B C 0.439(2) 0.254(2) 0.3955(13) 0.064(2) Uani 0.381(3) 1 d D . P A 2
H7B H 0.310010 0.205541 0.365452 0.076 Uiso 0.381(3) 1 calc R U P A 2
C8B C 0.5235(13) 0.236(2) 0.4824(10) 0.062(3) Uani 0.381(3) 1 d D . P A 2
H8B H 0.443761 0.194612 0.528809 0.074 Uiso 0.381(3) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 1.194(4) . ?
O2 C9 1.464(4) . ?
O2 B1 1.366(5) . ?
O3 C10 1.463(4) . ?
O3 B1 1.334(5) . ?
C1 C2 1.481(6) . ?
C1 C4 1.528(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.559(5) . ?
C3 H3 1.0000 . ?
C3 C4 1.557(5) . ?
C3 B1 1.572(6) . ?
C4 H4 1.0000 . ?
C4 C5 1.504(5) . ?
C5 C6A 1.3600(10) . ?
C5 C7A 1.4199(11) . ?
C5 C6B 1.3600(11) . ?
C5 C7B 1.4200(11) . ?
C9 C10 1.535(6) . ?
C9 C11 1.509(6) . ?
C9 C12 1.508(5) . ?
C10 C13 1.505(5) . ?
C10 C14 1.526(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
S1A C6A 1.7098(11) . ?
S1A C8A 1.7107(11) . ?
C6A H6A 0.9500 . ?
C7A H7A 0.9500 . ?
C7A C8A 1.3600(10) . ?
C8A H8A 0.9500 . ?
S1B C6B 1.7100(11) . ?
S1B C8B 1.7104(11) . ?
C6B H6B 0.9500 . ?
C7B H7B 0.9500 . ?
C7B C8B 1.3599(11) . ?
C8B H8B 0.9500 . ?

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 C9 106.1(3) . . ?
B1 O3 C10 107.0(3) . . ?
O1 C1 C2 134.2(4) . . ?
O1 C1 C4 132.8(4) . . ?
C2 C1 C4 92.7(3) . . ?
C1 C2 H2A 114.0 . . ?
C1 C2 H2B 114.0 . . ?
C1 C2 C3 88.2(3) . . ?
H2A C2 H2B 111.2 . . ?
C3 C2 H2A 114.0 . . ?
C3 C2 H2B 114.0 . . ?
C2 C3 H3 110.5 . . ?
C2 C3 B1 117.7(3) . . ?
C4 C3 C2 88.7(3) . . ?
C4 C3 H3 110.5 . . ?
C4 C3 B1 117.2(3) . . ?
B1 C3 H3 110.5 . . ?
C1 C4 C3 86.6(3) . . ?
C1 C4 H4 109.7 . . ?
C3 C4 H4 109.7 . . ?
C5 C4 C1 119.6(3) . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 109.7 . . ?
C6A C5 C4 124.6(3) . . ?
C6A C5 C7A 109.4(5) . . ?
C7A C5 C4 125.1(5) . . ?
C6B C5 C4 123.9(5) . . ?
C6B C5 C7B 112.6(8) . . ?
C7B C5 C4 121.9(6) . . ?
O2 C9 C10 102.2(3) . . ?
O2 C9 C11 106.9(4) . . ?
O2 C9 C12 108.3(3) . . ?
C11 C9 C10 112.7(4) . . ?
C12 C9 C10 115.8(4) . . ?
C12 C9 C11 110.2(4) . . ?
O3 C10 C9 102.3(3) . . ?
O3 C10 C13 107.9(3) . . ?
O3 C10 C14 107.0(3) . . ?
C13 C10 C9 115.8(4) . . ?
C13 C10 C14 110.0(4) . . ?
C14 C10 C9 113.0(4) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 B1 C3 121.9(4) . . ?
O3 B1 O2 114.1(4) . . ?
O3 B1 C3 124.1(4) . . ?
C6A S1A C8A 92.4(5) . . ?
C5 C6A S1A 112.3(3) . . ?
C5 C6A H6A 123.8 . . ?
S1A C6A H6A 123.8 . . ?
C5 C7A H7A 122.3 . . ?
C8A C7A C5 115.4(9) . . ?
C8A C7A H7A 122.3 . . ?
S1A C8A H8A 125.4 . . ?
C7A C8A S1A 109.2(8) . . ?
C7A C8A H8A 125.4 . . ?
C6B S1B C8B 91.4(8) . . ?
C5 C6B S1B 109.8(6) . . ?
C5 C6B H6B 125.1 . . ?
S1B C6B H6B 125.1 . . ?
C5 C7B H7B 125.4 . . ?
C8B C7B C5 109.2(11) . . ?
C8B C7B H7B 125.4 . . ?
S1B C8B H8B 123.9 . . ?
C7B C8B S1B 112.3(10) . . ?
C7B C8B H8B 123.9 . . ?

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 -159.7(5) . . . . ?
O1 C1 C4 C3 159.8(5) . . . . ?
O1 C1 C4 C5 37.5(7) . . . . ?
O2 C9 C10 O3 28.1(4) . . . . ?
O2 C9 C10 C13 145.2(3) . . . . ?
O2 C9 C10 C14 -86.6(4) . . . . ?
C1 C2 C3 C4 -14.6(3) . . . . ?
C1 C2 C3 B1 -134.9(4) . . . . ?
C1 C4 C5 C6A -47.1(9) . . . . ?
C1 C4 C5 C7A 145.6(10) . . . . ?
C1 C4 C5 C6B 132.1(17) . . . . ?
C1 C4 C5 C7B -32.3(13) . . . . ?
C2 C1 C4 C3 -14.9(3) . . . . ?
C2 C1 C4 C5 -137.2(4) . . . . ?
C2 C3 C4 C1 14.1(3) . . . . ?
C2 C3 C4 C5 136.5(4) . . . . ?
C2 C3 B1 O2 -176.8(4) . . . . ?
C2 C3 B1 O3 3.5(6) . . . . ?
C3 C4 C5 C6A -151.2(7) . . . . ?
C3 C4 C5 C7A 41.5(11) . . . . ?
C3 C4 C5 C6B 28.0(17) . . . . ?
C3 C4 C5 C7B -136.4(13) . . . . ?
C4 C1 C2 C3 14.9(3) . . . . ?
C4 C3 B1 O2 79.2(5) . . . . ?
C4 C3 B1 O3 -100.5(5) . . . . ?
C4 C5 C6A S1A 179.1(4) . . . . ?
C4 C5 C7A C8A -179.1(10) . . . . ?
C4 C5 C6B S1B 173.7(9) . . . . ?
C4 C5 C7B C8B -170.0(12) . . . . ?
C5 C7A C8A S1A -6.4(18) . . . . ?
C5 C7B C8B S1B -16(2) . . . . ?
C9 O2 B1 O3 10.0(5) . . . . ?
C9 O2 B1 C3 -169.7(4) . . . . ?
C10 O3 B1 O2 9.3(5) . . . . ?
C10 O3 B1 C3 -171.0(4) . . . . ?
C11 C9 C10 O3 -86.3(4) . . . . ?
C11 C9 C10 C13 30.8(5) . . . . ?
C11 C9 C10 C14 159.0(4) . . . . ?
C12 C9 C10 O3 145.6(3) . . . . ?
C12 C9 C10 C13 -97.4(5) . . . . ?
C12 C9 C10 C14 30.8(5) . . . . ?
B1 O2 C9 C10 -23.6(4) . . . . ?
B1 O2 C9 C11 94.9(4) . . . . ?
B1 O2 C9 C12 -146.3(4) . . . . ?
B1 O3 C10 C9 -23.4(4) . . . . ?
B1 O3 C10 C13 -146.0(4) . . . . ?
B1 O3 C10 C14 95.6(4) . . . . ?
B1 C3 C4 C1 134.9(4) . . . . ?
B1 C3 C4 C5 -102.7(4) . . . . ?
C6A C5 C7A C8A 12.0(17) . . . . ?
C6A S1A C8A C7A -0.5(13) . . . . ?
C7A C5 C6A S1A -11.9(13) . . . . ?
C8A S1A C6A C5 7.4(10) . . . . ?
C6B C5 C7B C8B 24(2) . . . . ?
C6B S1B C8B C7B 4(2) . . . . ?
C7B C5 C6B S1B -21(2) . . . . ?
C8B S1B C6B C5 9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_v131
_database_code_depnum_ccdc_archive 'CCDC 2312008'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;Institute of Organic Chemistry of the National Academy of Sciences of Ukraine
Ukraine
;
_audit_update_record             
;
2023-12-04 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_audit_creation_date             2023-03-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-7-oxaspiro[3.5]nonan-1-one
_chemical_formula_moiety         'C14 H23 B O4'
_chemical_formula_sum            'C14 H23 B O4'
_chemical_formula_weight         266.13
_chemical_absolute_configuration ?
_chemical_melting_point          354
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.847(4)
_cell_length_b                   6.213(2)
_cell_length_c                   11.060(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.661(8)
_cell_angle_gamma                90
_cell_volume                     717.7(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3980
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_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_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_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       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_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_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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)'
_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_coef       .
_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_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0972
_refine_ls_restrained_S_all      1.177
_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/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2727
_refine_ls_wR_factor_ref         0.2817
_refine_special_details          
;
 Refined as a 2-component twin.
;
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 -0.0548(5) 0.5676(10) 0.5396(6) 0.0331(14) Uani 1 1 d . . . . .
O4 O 0.4377(5) 0.4108(9) 0.6291(6) 0.0299(14) Uani 1 1 d . . . . .
O2 O 0.0429(5) 0.6222(11) 0.9171(5) 0.0354(15) Uani 1 1 d . . . . .
O3 O 0.4751(5) 0.6371(10) 0.7988(5) 0.0289(13) Uani 1 1 d . . . . .
C3 C 0.0594(6) 0.5886(11) 0.5766(7) 0.0220(16) Uani 1 1 d . . . . .
C6 C 0.0105(8) 0.7957(15) 0.8309(9) 0.0309(19) Uani 1 1 d . . . . .
H6A H -0.006740 0.925409 0.875740 0.037 Uiso 1 1 calc R U . . .
H6B H -0.068935 0.759503 0.765423 0.037 Uiso 1 1 calc R U . . .
C14 C 0.6464(8) 0.5245(15) 0.6229(8) 0.033(2) Uani 1 1 d . . . . .
H14A H 0.620411 0.481600 0.534377 0.049 Uiso 1 1 calc R U . . .
H14B H 0.738804 0.503305 0.656760 0.049 Uiso 1 1 calc R U . . .
H14C H 0.625522 0.676641 0.630112 0.049 Uiso 1 1 calc R U . . .
C9 C 0.5811(7) 0.4826(14) 0.8280(8) 0.0265(18) Uani 1 1 d . . . . .
C8 C 0.1750(7) 0.4557(13) 0.7960(8) 0.0270(17) Uani 1 1 d . . . . .
H8A H 0.184599 0.321806 0.750829 0.032 Uiso 1 1 calc R U . . .
H8B H 0.255247 0.479543 0.862929 0.032 Uiso 1 1 calc R U . . .
C2 C 0.1664(7) 0.5792(15) 0.5109(7) 0.0269(17) Uani 1 1 d . . . . .
H2A H 0.151688 0.672409 0.435713 0.032 Uiso 1 1 calc R U . . .
H2B H 0.190004 0.431312 0.492334 0.032 Uiso 1 1 calc R U . . .
C4 C 0.1510(6) 0.6462(12) 0.7043(7) 0.0182(15) Uani 1 1 d . . . . .
C5 C 0.1157(7) 0.8452(12) 0.7690(8) 0.0234(17) Uani 1 1 d . . . . .
H5A H 0.192295 0.897183 0.833140 0.028 Uiso 1 1 calc R U . . .
H5B H 0.086960 0.961105 0.706299 0.028 Uiso 1 1 calc R U . . .
C7 C 0.0641(8) 0.4326(14) 0.8537(9) 0.0315(19) Uani 1 1 d . . . . .
H7A H -0.014517 0.398111 0.786778 0.038 Uiso 1 1 calc R U . . .
H7B H 0.081428 0.311159 0.913860 0.038 Uiso 1 1 calc R U . . .
C13 C 0.6110(9) 0.1542(14) 0.6957(10) 0.039(2) Uani 1 1 d . . . . .
H13A H 0.564931 0.071658 0.745178 0.059 Uiso 1 1 calc R U . . .
H13B H 0.703422 0.137673 0.732268 0.059 Uiso 1 1 calc R U . . .
H13C H 0.587694 0.100963 0.609067 0.059 Uiso 1 1 calc R U . . .
C10 C 0.5756(7) 0.3882(13) 0.6965(8) 0.0288(19) Uani 1 1 d . . . . .
B1 B 0.3929(7) 0.5729(14) 0.6878(8) 0.0209(17) Uani 1 1 d . . . . .
C12 C 0.7034(7) 0.5976(16) 0.8931(8) 0.033(2) Uani 1 1 d . . . . .
H12A H 0.716986 0.717986 0.840944 0.050 Uiso 1 1 calc R U . . .
H12B H 0.775470 0.497204 0.906460 0.050 Uiso 1 1 calc R U . . .
H12C H 0.697143 0.652471 0.974365 0.050 Uiso 1 1 calc R U . . .
C1 C 0.2573(7) 0.6788(12) 0.6311(7) 0.0221(17) Uani 1 1 d . . . . .
H1 H 0.268148 0.835971 0.617443 0.026 Uiso 1 1 calc R U . . .
C11 C 0.5487(9) 0.3134(17) 0.9149(8) 0.039(2) Uani 1 1 d . . . . .
H11A H 0.533934 0.384264 0.988859 0.058 Uiso 1 1 calc R U . . .
H11B H 0.620148 0.212004 0.941372 0.058 Uiso 1 1 calc R U . . .
H11C H 0.471344 0.235391 0.870071 0.058 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C3 1.202(8) . ?
O4 C10 1.487(9) . ?
O4 B1 1.358(10) . ?
O2 C6 1.418(11) . ?
O2 C7 1.421(11) . ?
O3 C9 1.466(9) . ?
O3 B1 1.368(10) . ?
C3 C2 1.528(9) . ?
C3 C4 1.533(10) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.513(11) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14 C10 1.518(12) . ?
C9 C10 1.555(12) . ?
C9 C12 1.508(11) . ?
C9 C11 1.527(12) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C4 1.535(10) . ?
C8 C7 1.514(11) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.555(11) . ?
C4 C5 1.528(10) . ?
C4 C1 1.590(9) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 C10 1.504(11) . ?
B1 C1 1.578(11) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C1 H1 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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 O4 C10 105.8(6) . . ?
C6 O2 C7 110.0(6) . . ?
B1 O3 C9 106.8(6) . . ?
O1 C3 C2 132.7(7) . . ?
O1 C3 C4 133.7(7) . . ?
C2 C3 C4 93.5(5) . . ?
O2 C6 H6A 109.2 . . ?
O2 C6 H6B 109.2 . . ?
O2 C6 C5 112.2(7) . . ?
H6A C6 H6B 107.9 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
O3 C9 C10 102.2(6) . . ?
O3 C9 C12 109.3(7) . . ?
O3 C9 C11 106.8(6) . . ?
C12 C9 C10 115.6(7) . . ?
C12 C9 C11 110.3(7) . . ?
C11 C9 C10 111.8(7) . . ?
H8A C8 H8B 108.2 . . ?
C4 C8 H8A 109.7 . . ?
C4 C8 H8B 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C7 C8 C4 109.8(6) . . ?
C3 C2 H2A 114.0 . . ?
C3 C2 H2B 114.0 . . ?
C3 C2 C1 88.0(5) . . ?
H2A C2 H2B 111.2 . . ?
C1 C2 H2A 114.0 . . ?
C1 C2 H2B 114.0 . . ?
C3 C4 C8 112.4(6) . . ?
C3 C4 C1 86.6(5) . . ?
C8 C4 C1 114.7(6) . . ?
C5 C4 C3 116.0(6) . . ?
C5 C4 C8 109.5(6) . . ?
C5 C4 C1 116.3(6) . . ?
C6 C5 C4 111.3(6) . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
O2 C7 C8 112.5(7) . . ?
O2 C7 H7A 109.1 . . ?
O2 C7 H7B 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
O4 C10 C14 105.3(6) . . ?
O4 C10 C9 102.3(6) . . ?
O4 C10 C13 108.2(7) . . ?
C14 C10 C9 113.2(7) . . ?
C13 C10 C14 111.7(7) . . ?
C13 C10 C9 115.1(8) . . ?
O4 B1 O3 114.5(7) . . ?
O4 B1 C1 122.3(7) . . ?
O3 B1 C1 123.1(7) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C1 C4 90.3(5) . . ?
C2 C1 B1 118.8(6) . . ?
C2 C1 H1 109.4 . . ?
C4 C1 H1 109.4 . . ?
B1 C1 C4 118.1(6) . . ?
B1 C1 H1 109.4 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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 C3 C2 C1 167.2(9) . . . . ?
O1 C3 C4 C8 77.3(10) . . . . ?
O1 C3 C4 C5 -49.6(11) . . . . ?
O1 C3 C4 C1 -167.3(9) . . . . ?
O4 B1 C1 C2 6.2(10) . . . . ?
O4 B1 C1 C4 113.7(8) . . . . ?
O2 C6 C5 C4 55.8(9) . . . . ?
O3 C9 C10 O4 -28.4(7) . . . . ?
O3 C9 C10 C14 84.5(8) . . . . ?
O3 C9 C10 C13 -145.4(7) . . . . ?
O3 B1 C1 C2 -174.3(6) . . . . ?
O3 B1 C1 C4 -66.8(9) . . . . ?
C3 C2 C1 C4 9.6(6) . . . . ?
C3 C2 C1 B1 132.3(6) . . . . ?
C3 C4 C5 C6 78.3(8) . . . . ?
C3 C4 C1 C2 -9.6(6) . . . . ?
C3 C4 C1 B1 -132.9(6) . . . . ?
C6 O2 C7 C8 62.2(9) . . . . ?
C9 O3 B1 O4 -8.3(8) . . . . ?
C9 O3 B1 C1 172.2(7) . . . . ?
C8 C4 C5 C6 -50.1(8) . . . . ?
C8 C4 C1 C2 103.5(7) . . . . ?
C8 C4 C1 B1 -19.8(9) . . . . ?
C2 C3 C4 C8 -105.5(7) . . . . ?
C2 C3 C4 C5 127.5(6) . . . . ?
C2 C3 C4 C1 9.8(6) . . . . ?
C4 C3 C2 C1 -10.0(6) . . . . ?
C4 C8 C7 O2 -57.7(9) . . . . ?
C5 C4 C1 C2 -127.0(7) . . . . ?
C5 C4 C1 B1 109.7(8) . . . . ?
C7 O2 C6 C5 -60.6(9) . . . . ?
C7 C8 C4 C3 -79.8(8) . . . . ?
C7 C8 C4 C5 50.6(8) . . . . ?
C7 C8 C4 C1 -176.6(7) . . . . ?
C10 O4 B1 O3 -11.1(8) . . . . ?
C10 O4 B1 C1 168.4(7) . . . . ?
B1 O4 C10 C14 -94.2(7) . . . . ?
B1 O4 C10 C9 24.3(8) . . . . ?
B1 O4 C10 C13 146.2(7) . . . . ?
B1 O3 C9 C10 22.9(7) . . . . ?
B1 O3 C9 C12 145.9(7) . . . . ?
B1 O3 C9 C11 -94.7(7) . . . . ?
C12 C9 C10 O4 -147.0(7) . . . . ?
C12 C9 C10 C14 -34.2(10) . . . . ?
C12 C9 C10 C13 95.9(9) . . . . ?
C1 C4 C5 C6 177.9(6) . . . . ?
C11 C9 C10 O4 85.6(7) . . . . ?
C11 C9 C10 C14 -161.6(7) . . . . ?
C11 C9 C10 C13 -31.5(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.752(7)
2 0.248(7)

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_v52
_database_code_depnum_ccdc_archive 'CCDC 2312009'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;Institute of Organic Chemistry of the National Academy of Sciences of Ukraine
Ukraine
;
_audit_update_record             
;
2023-12-04 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_audit_creation_date             2022-11-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
3-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[3.3]heptan-1-one
_chemical_formula_moiety         'C14 H23 B O3'
_chemical_formula_sum            'C14 H23 B O3'
_chemical_formula_weight         250.13
_chemical_melting_point          338
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.489(2)
_cell_length_b                   14.273(3)
_cell_length_c                   11.565(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.466(15)
_cell_angle_gamma                90
_cell_volume                     1494.2(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1734
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      18.36
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.112
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1174
_diffrn_reflns_av_unetI/netI     0.1067
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16753
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        24.989
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_min         2.250
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_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_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1110
_reflns_number_total             2508
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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)'
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2508
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1679
_refine_ls_R_factor_gt           0.0829
_refine_ls_restrained_S_all      0.883
_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)+(0.1392P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2118
_refine_ls_wR_factor_ref         0.2449
_refine_special_details          ?
_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:
 C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.8075(3) 0.5019(2) 0.4175(3) 0.0848(10) Uani 1 1 d . . . . .
O2 O 0.7609(3) 0.8583(2) 0.2798(3) 0.0846(10) Uani 1 1 d . . . . .
O3 O 0.6383(3) 0.76408(18) 0.3703(3) 0.0844(10) Uani 1 1 d . . . . .
C1 C 0.9099(4) 0.7216(2) 0.4000(3) 0.0555(10) Uani 1 1 d . . . . .
C2 C 0.9050(5) 0.6563(2) 0.5077(4) 0.0678(11) Uani 1 1 d . . . . .
H2A H 0.999899 0.647614 0.568451 0.081 Uiso 1 1 calc R U . . .
H2B H 0.828977 0.672718 0.544501 0.081 Uiso 1 1 calc R U . . .
C3 C 0.8621(4) 0.5776(3) 0.4155(4) 0.0581(10) Uani 1 1 d . . . . .
C4 C 0.9003(4) 0.6328(2) 0.3179(3) 0.0535(10) Uani 1 1 d . . . . .
C5 C 0.8055(5) 0.6176(3) 0.1871(4) 0.0753(12) Uani 1 1 d . . . . .
H5A H 0.794173 0.673247 0.136911 0.090 Uiso 1 1 calc R U . . .
H5B H 0.710563 0.588906 0.179570 0.090 Uiso 1 1 calc R U . . .
C6 C 0.9229(6) 0.5483(3) 0.1702(5) 0.1012(17) Uani 1 1 d . . . . .
H6A H 0.948081 0.557246 0.095577 0.121 Uiso 1 1 calc R U . . .
H6B H 0.900913 0.483070 0.180971 0.121 Uiso 1 1 calc R U . . .
C7 C 1.0342(5) 0.5930(3) 0.2828(5) 0.0839(14) Uani 1 1 d . . . . .
H7A H 1.096522 0.640712 0.263693 0.101 Uiso 1 1 calc R U . . .
H7B H 1.092352 0.547894 0.340236 0.101 Uiso 1 1 calc R U . . .
C8 C 1.0525(4) 0.7790(3) 0.4222(4) 0.0843(13) Uani 1 1 d . . . . .
H8A H 1.136428 0.738407 0.451202 0.126 Uiso 1 1 calc R U . . .
H8B H 1.055546 0.826552 0.481608 0.126 Uiso 1 1 calc R U . . .
H8C H 1.054640 0.807856 0.347811 0.126 Uiso 1 1 calc R U . . .
C9 C 0.6147(5) 0.8992(3) 0.2551(4) 0.0847(14) Uani 1 1 d . . . . .
C10 C 0.5252(4) 0.8238(3) 0.2928(4) 0.0734(12) Uani 1 1 d . . . . .
C11 C 0.6417(9) 0.9854(4) 0.3418(11) 0.208(5) Uani 1 1 d . . . . .
H11A H 0.627275 0.967264 0.417373 0.313 Uiso 1 1 calc R U . . .
H11B H 0.573384 1.034317 0.305374 0.313 Uiso 1 1 calc R U . . .
H11C H 0.740922 1.007525 0.355953 0.313 Uiso 1 1 calc R U . . .
C12 C 0.5652(7) 0.9318(7) 0.1280(6) 0.220(5) Uani 1 1 d . . . . .
H12A H 0.645865 0.962011 0.108849 0.330 Uiso 1 1 calc R U . . .
H12B H 0.485352 0.975455 0.117453 0.330 Uiso 1 1 calc R U . . .
H12C H 0.532326 0.879208 0.075052 0.330 Uiso 1 1 calc R U . . .
C13 C 0.4284(7) 0.8588(5) 0.3651(7) 0.159(3) Uani 1 1 d . . . . .
H13A H 0.383600 0.806469 0.392659 0.238 Uiso 1 1 calc R U . . .
H13B H 0.352802 0.898497 0.315123 0.238 Uiso 1 1 calc R U . . .
H13C H 0.487023 0.893667 0.433638 0.238 Uiso 1 1 calc R U . . .
C14 C 0.4375(9) 0.7649(6) 0.1919(9) 0.249(6) Uani 1 1 d . . . . .
H14A H 0.470357 0.774749 0.122037 0.374 Uiso 1 1 calc R U . . .
H14B H 0.335003 0.781534 0.172857 0.374 Uiso 1 1 calc R U . . .
H14C H 0.449971 0.700189 0.215262 0.374 Uiso 1 1 calc R U . . .
B1 B 0.7669(5) 0.7819(3) 0.3495(4) 0.0539(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C3 1.201(4) . ?
O2 C9 1.453(4) . ?
O2 B1 1.347(5) . ?
O3 C10 1.451(4) . ?
O3 B1 1.337(5) . ?
C1 C2 1.567(5) . ?
C1 C4 1.568(5) . ?
C1 C8 1.536(5) . ?
C1 B1 1.565(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.518(5) . ?
C3 C4 1.507(5) . ?
C4 C5 1.526(5) . ?
C4 C7 1.553(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.546(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.547(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.514(6) . ?
C9 C11 1.558(9) . ?
C9 C12 1.477(7) . ?
C10 C13 1.501(6) . ?
C10 C14 1.476(8) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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 C9 108.1(3) . . ?
B1 O3 C10 108.8(3) . . ?
C2 C1 C4 89.5(2) . . ?
C8 C1 C2 114.8(3) . . ?
C8 C1 C4 114.9(3) . . ?
C8 C1 B1 113.0(3) . . ?
B1 C1 C2 113.2(3) . . ?
B1 C1 C4 109.4(3) . . ?
C1 C2 H2A 114.2 . . ?
C1 C2 H2B 114.2 . . ?
H2A C2 H2B 111.3 . . ?
C3 C2 C1 87.0(3) . . ?
C3 C2 H2A 114.2 . . ?
C3 C2 H2B 114.2 . . ?
O1 C3 C2 132.7(4) . . ?
O1 C3 C4 133.4(4) . . ?
C4 C3 C2 93.7(3) . . ?
C3 C4 C1 87.3(2) . . ?
C3 C4 C5 117.8(3) . . ?
C3 C4 C7 113.8(3) . . ?
C5 C4 C1 128.7(3) . . ?
C5 C4 C7 88.5(3) . . ?
C7 C4 C1 123.3(3) . . ?
C4 C5 H5A 113.8 . . ?
C4 C5 H5B 113.8 . . ?
C4 C5 C6 89.1(3) . . ?
H5A C5 H5B 111.0 . . ?
C6 C5 H5A 113.8 . . ?
C6 C5 H5B 113.8 . . ?
C5 C6 H6A 114.0 . . ?
C5 C6 H6B 114.0 . . ?
C5 C6 C7 87.9(3) . . ?
H6A C6 H6B 111.2 . . ?
C7 C6 H6A 114.0 . . ?
C7 C6 H6B 114.0 . . ?
C4 C7 H7A 114.0 . . ?
C4 C7 H7B 114.0 . . ?
C6 C7 C4 88.1(3) . . ?
C6 C7 H7A 114.0 . . ?
C6 C7 H7B 114.0 . . ?
H7A C7 H7B 111.2 . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 C10 104.0(3) . . ?
O2 C9 C11 103.2(5) . . ?
O2 C9 C12 108.8(4) . . ?
C10 C9 C11 111.9(5) . . ?
C12 C9 C10 118.2(6) . . ?
C12 C9 C11 109.5(6) . . ?
O3 C10 C9 102.8(3) . . ?
O3 C10 C13 108.3(4) . . ?
O3 C10 C14 106.9(4) . . ?
C13 C10 C9 114.5(4) . . ?
C14 C10 C9 114.2(6) . . ?
C14 C10 C13 109.6(6) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 B1 C1 123.0(3) . . ?
O3 B1 O2 112.6(3) . . ?
O3 B1 C1 124.4(3) . . ?

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 C3 C4 C1 162.9(4) . . . . ?
O1 C3 C4 C5 29.9(6) . . . . ?
O1 C3 C4 C7 -71.6(5) . . . . ?
O2 C9 C10 O3 18.5(4) . . . . ?
O2 C9 C10 C13 135.7(5) . . . . ?
O2 C9 C10 C14 -96.9(5) . . . . ?
C1 C2 C3 O1 -162.9(4) . . . . ?
C1 C2 C3 C4 12.3(3) . . . . ?
C1 C4 C5 C6 152.1(3) . . . . ?
C1 C4 C7 C6 -155.9(3) . . . . ?
C2 C1 C4 C3 11.8(3) . . . . ?
C2 C1 C4 C5 135.9(4) . . . . ?
C2 C1 C4 C7 -105.1(4) . . . . ?
C2 C1 B1 O2 162.7(3) . . . . ?
C2 C1 B1 O3 -17.1(5) . . . . ?
C2 C3 C4 C1 -12.2(3) . . . . ?
C2 C3 C4 C5 -145.3(3) . . . . ?
C2 C3 C4 C7 113.3(4) . . . . ?
C3 C4 C5 C6 -97.2(3) . . . . ?
C3 C4 C7 C6 100.8(4) . . . . ?
C4 C1 C2 C3 -11.7(2) . . . . ?
C4 C1 B1 O2 -99.2(4) . . . . ?
C4 C1 B1 O3 80.9(4) . . . . ?
C4 C5 C6 C7 -19.1(3) . . . . ?
C5 C4 C7 C6 -19.0(3) . . . . ?
C5 C6 C7 C4 18.8(3) . . . . ?
C7 C4 C5 C6 19.0(3) . . . . ?
C8 C1 C2 C3 -129.1(3) . . . . ?
C8 C1 C4 C3 129.1(3) . . . . ?
C8 C1 C4 C5 -106.9(4) . . . . ?
C8 C1 C4 C7 12.1(5) . . . . ?
C8 C1 B1 O2 30.1(5) . . . . ?
C8 C1 B1 O3 -149.7(4) . . . . ?
C9 O2 B1 O3 2.8(5) . . . . ?
C9 O2 B1 C1 -177.0(4) . . . . ?
C10 O3 B1 O2 10.0(4) . . . . ?
C10 O3 B1 C1 -170.1(4) . . . . ?
C11 C9 C10 O3 -92.2(5) . . . . ?
C11 C9 C10 C13 25.0(6) . . . . ?
C11 C9 C10 C14 152.4(6) . . . . ?
C12 C9 C10 O3 139.2(5) . . . . ?
C12 C9 C10 C13 -103.6(6) . . . . ?
C12 C9 C10 C14 23.8(7) . . . . ?
B1 O2 C9 C10 -13.7(5) . . . . ?
B1 O2 C9 C11 103.3(5) . . . . ?
B1 O2 C9 C12 -140.5(6) . . . . ?
B1 O3 C10 C9 -17.7(4) . . . . ?
B1 O3 C10 C13 -139.2(5) . . . . ?
B1 O3 C10 C14 102.8(6) . . . . ?
B1 C1 C2 C3 99.2(3) . . . . ?
B1 C1 C4 C3 -102.6(3) . . . . ?
B1 C1 C4 C5 21.4(5) . . . . ?
B1 C1 C4 C7 140.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_v288
_database_code_depnum_ccdc_archive 'CCDC 2321052'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;Institute of Organic Chemistry of the National Academy of Sciences of Ukraine
Ukraine
;
_audit_update_record             
;
2023-12-21 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_audit_creation_date             2023-12-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
(2r,3r)-2-(4-Bromophenyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclobutanone
_chemical_formula_moiety         'C16 H20 B Br O3'
_chemical_formula_sum            'C16 H20 B Br O3'
_chemical_formula_weight         351.04
_chemical_melting_point          379
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1342(11)
_cell_length_b                   8.6448(14)
_cell_length_c                   16.040(3)
_cell_angle_alpha                74.401(10)
_cell_angle_beta                 86.768(16)
_cell_angle_gamma                89.349(12)
_cell_volume                     817.9(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2548
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.21
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.824
_shelx_estimated_absorpt_T_min   0.689
_exptl_absorpt_coefficient_mu    2.519
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0731
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_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       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11153
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.446
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_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       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1759
_reflns_number_total             2874
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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)'
_refine_diff_density_max         1.168
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2874
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0768
_refine_ls_restrained_S_all      1.032
_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)+(0.1247P)²+0.6183P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2001
_refine_ls_wR_factor_ref         0.2234
_refine_special_details          ?
_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), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c), C14(H14a,H14b,H14c), C15(H15a,H15b,H15c), C16(H16a,H16b,
 H16c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br1 Br 0.27409(18) 1.34217(10) 0.44602(5) 0.1006(5) Uani 1 1 d . . . . .
O1 O 0.8098(7) 0.9235(6) 0.8297(3) 0.0666(13) Uani 1 1 d . . . . .
O2 O 0.0705(6) 0.5574(4) 0.7849(2) 0.0460(10) Uani 1 1 d . . . . .
O3 O 0.2966(6) 0.4202(4) 0.8871(2) 0.0412(9) Uani 1 1 d . . . . .
C1 C 0.6602(10) 0.8318(7) 0.8321(4) 0.0438(14) Uani 1 1 d . . . . .
C2 C 0.5219(10) 0.7263(7) 0.9038(4) 0.0464(15) Uani 1 1 d . . . . .
H2A H 0.472522 0.777651 0.949768 0.056 Uiso 1 1 calc R U . . .
H2B H 0.585703 0.619234 0.928850 0.056 Uiso 1 1 calc R U . . .
C3 C 0.3502(8) 0.7275(6) 0.8371(3) 0.0346(12) Uani 1 1 d . . . . .
H3 H 0.237432 0.810927 0.839527 0.041 Uiso 1 1 calc R U . . .
C4 C 0.5271(9) 0.7984(6) 0.7617(3) 0.0382(13) Uani 1 1 d . . . . .
H4 H 0.595987 0.708677 0.741288 0.046 Uiso 1 1 calc R U . . .
C5 C 0.4668(9) 0.9307(6) 0.6848(3) 0.0412(14) Uani 1 1 d . . . . .
C6 C 0.6120(11) 1.0543(7) 0.6460(4) 0.0514(15) Uani 1 1 d . . . . .
H6 H 0.751111 1.055543 0.669081 0.062 Uiso 1 1 calc R U . . .
C7 C 0.5583(13) 1.1762(8) 0.5742(4) 0.0631(19) Uani 1 1 d . . . . .
H7 H 0.659649 1.259557 0.547720 0.076 Uiso 1 1 calc R U . . .
C8 C 0.3555(13) 1.1737(7) 0.5422(4) 0.0551(17) Uani 1 1 d . . . . .
C9 C 0.2105(12) 1.0545(8) 0.5791(4) 0.0611(18) Uani 1 1 d . . . . .
H9 H 0.071928 1.054491 0.555528 0.073 Uiso 1 1 calc R U . . .
C10 C 0.2620(10) 0.9334(7) 0.6506(4) 0.0503(15) Uani 1 1 d . . . . .
H10 H 0.158041 0.851540 0.676570 0.060 Uiso 1 1 calc R U . . .
C11 C 0.0460(9) 0.3875(7) 0.7872(4) 0.0405(13) Uani 1 1 d . . . . .
C12 C 0.1392(9) 0.3014(6) 0.8767(4) 0.0397(13) Uani 1 1 d . . . . .
C13 C 0.1837(11) 0.3611(9) 0.7111(4) 0.0619(18) Uani 1 1 d . . . . .
H13A H 0.135845 0.434053 0.657261 0.093 Uiso 1 1 calc R U . . .
H13B H 0.167174 0.249744 0.708763 0.093 Uiso 1 1 calc R U . . .
H13C H 0.337331 0.382441 0.717859 0.093 Uiso 1 1 calc R U . . .
C14 C -0.1925(10) 0.3551(8) 0.7801(4) 0.0564(17) Uani 1 1 d . . . . .
H14A H -0.280403 0.396845 0.822092 0.085 Uiso 1 1 calc R U . . .
H14B H -0.216608 0.239142 0.792156 0.085 Uiso 1 1 calc R U . . .
H14C H -0.235419 0.408381 0.721345 0.085 Uiso 1 1 calc R U . . .
C15 C 0.2559(11) 0.1462(7) 0.8808(5) 0.0645(19) Uani 1 1 d . . . . .
H15A H 0.385562 0.166750 0.840770 0.097 Uiso 1 1 calc R U . . .
H15B H 0.158142 0.071901 0.864290 0.097 Uiso 1 1 calc R U . . .
H15C H 0.300204 0.098690 0.939958 0.097 Uiso 1 1 calc R U . . .
C16 C -0.0320(11) 0.2803(9) 0.9516(4) 0.0631(18) Uani 1 1 d . . . . .
H16A H 0.038080 0.240212 1.006660 0.095 Uiso 1 1 calc R U . . .
H16B H -0.143119 0.203198 0.946583 0.095 Uiso 1 1 calc R U . . .
H16C H -0.101046 0.383907 0.949627 0.095 Uiso 1 1 calc R U . . .
B11 B 0.2340(10) 0.5648(7) 0.8367(4) 0.0341(14) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Br1 C8 1.900(6) . ?
O1 C1 1.212(7) . ?
O2 C11 1.469(7) . ?
O2 B11 1.350(7) . ?
O3 C12 1.465(6) . ?
O3 B11 1.359(7) . ?
C1 C2 1.490(8) . ?
C1 C4 1.520(8) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.541(8) . ?
C3 H3 1.0000 . ?
C3 C4 1.577(7) . ?
C3 B11 1.586(8) . ?
C4 H4 1.0000 . ?
C4 C5 1.500(8) . ?
C5 C6 1.387(8) . ?
C5 C10 1.397(8) . ?
C6 H6 0.9500 . ?
C6 C7 1.389(9) . ?
C7 H7 0.9500 . ?
C7 C8 1.375(10) . ?
C8 C9 1.356(10) . ?
C9 H9 0.9500 . ?
C9 C10 1.377(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.565(8) . ?
C11 C13 1.511(8) . ?
C11 C14 1.509(8) . ?
C12 C15 1.501(8) . ?
C12 C16 1.524(8) . ?
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_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
B11 O2 C11 106.5(4) . . ?
B11 O3 C12 106.7(4) . . ?
O1 C1 C2 133.7(5) . . ?
O1 C1 C4 132.3(5) . . ?
C2 C1 C4 93.6(4) . . ?
C1 C2 H2A 114.0 . . ?
C1 C2 H2B 114.0 . . ?
C1 C2 C3 87.8(4) . . ?
H2A C2 H2B 111.2 . . ?
C3 C2 H2A 114.0 . . ?
C3 C2 H2B 114.0 . . ?
C2 C3 H3 109.7 . . ?
C2 C3 C4 89.5(4) . . ?
C2 C3 B11 119.6(4) . . ?
C4 C3 H3 109.7 . . ?
C4 C3 B11 117.2(4) . . ?
B11 C3 H3 109.7 . . ?
C1 C4 C3 85.5(4) . . ?
C1 C4 H4 109.4 . . ?
C3 C4 H4 109.4 . . ?
C5 C4 C1 121.3(5) . . ?
C5 C4 C3 119.8(5) . . ?
C5 C4 H4 109.4 . . ?
C6 C5 C4 121.0(5) . . ?
C6 C5 C10 118.1(5) . . ?
C10 C5 C4 120.9(5) . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.3(6) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 120.7 . . ?
C8 C7 C6 118.7(6) . . ?
C8 C7 H7 120.7 . . ?
C7 C8 Br1 119.7(5) . . ?
C9 C8 Br1 119.3(5) . . ?
C9 C8 C7 121.0(6) . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.7(6) . . ?
C10 C9 H9 119.6 . . ?
C5 C10 H10 120.0 . . ?
C9 C10 C5 120.1(6) . . ?
C9 C10 H10 120.0 . . ?
O2 C11 C12 101.7(4) . . ?
O2 C11 C13 106.8(5) . . ?
O2 C11 C14 108.2(5) . . ?
C13 C11 C12 113.0(5) . . ?
C14 C11 C12 114.7(5) . . ?
C14 C11 C13 111.6(5) . . ?
O3 C12 C11 101.9(4) . . ?
O3 C12 C15 108.9(4) . . ?
O3 C12 C16 106.5(5) . . ?
C15 C12 C11 115.6(5) . . ?
C15 C12 C16 110.6(5) . . ?
C16 C12 C11 112.4(5) . . ?
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 B11 O3 114.5(5) . . ?
O2 B11 C3 123.3(5) . . ?
O3 B11 C3 122.2(5) . . ?

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
Br1 C8 C9 C10 -178.0(5) . . . . ?
O1 C1 C2 C3 158.7(7) . . . . ?
O1 C1 C4 C3 -159.1(7) . . . . ?
O1 C1 C4 C5 -36.7(9) . . . . ?
O2 C11 C12 O3 -28.6(5) . . . . ?
O2 C11 C12 C15 -146.6(5) . . . . ?
O2 C11 C12 C16 85.1(5) . . . . ?
C1 C2 C3 C4 14.2(4) . . . . ?
C1 C2 C3 B11 135.6(5) . . . . ?
C1 C4 C5 C6 38.1(8) . . . . ?
C1 C4 C5 C10 -141.5(6) . . . . ?
C2 C1 C4 C3 14.5(4) . . . . ?
C2 C1 C4 C5 136.9(5) . . . . ?
C2 C3 C4 C1 -13.9(4) . . . . ?
C2 C3 C4 C5 -137.7(5) . . . . ?
C2 C3 B11 O2 174.8(5) . . . . ?
C2 C3 B11 O3 -7.1(8) . . . . ?
C3 C4 C5 C6 142.2(5) . . . . ?
C3 C4 C5 C10 -37.4(7) . . . . ?
C4 C1 C2 C3 -14.8(4) . . . . ?
C4 C3 B11 O2 -78.9(7) . . . . ?
C4 C3 B11 O3 99.1(6) . . . . ?
C4 C5 C6 C7 179.2(5) . . . . ?
C4 C5 C10 C9 -179.0(5) . . . . ?
C5 C6 C7 C8 0.7(9) . . . . ?
C6 C5 C10 C9 1.4(9) . . . . ?
C6 C7 C8 Br1 178.2(4) . . . . ?
C6 C7 C8 C9 -0.5(10) . . . . ?
C7 C8 C9 C10 0.7(10) . . . . ?
C8 C9 C10 C5 -1.2(10) . . . . ?
C10 C5 C6 C7 -1.2(9) . . . . ?
C11 O2 B11 O3 -12.2(6) . . . . ?
C11 O2 B11 C3 166.0(5) . . . . ?
C12 O3 B11 O2 -7.8(6) . . . . ?
C12 O3 B11 C3 174.0(5) . . . . ?
C13 C11 C12 O3 85.5(5) . . . . ?
C13 C11 C12 C15 -32.5(7) . . . . ?
C13 C11 C12 C16 -160.8(5) . . . . ?
C14 C11 C12 O3 -145.1(5) . . . . ?
C14 C11 C12 C15 96.9(6) . . . . ?
C14 C11 C12 C16 -31.4(7) . . . . ?
B11 O2 C11 C12 25.1(5) . . . . ?
B11 O2 C11 C13 -93.5(5) . . . . ?
B11 O2 C11 C14 146.2(5) . . . . ?
B11 O3 C12 C11 22.7(5) . . . . ?
B11 O3 C12 C15 145.3(5) . . . . ?
B11 O3 C12 C16 -95.3(5) . . . . ?
B11 C3 C4 C1 -137.4(5) . . . . ?
B11 C3 C4 C5 98.9(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vd49
_database_code_depnum_ccdc_archive 'CCDC 2312010'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;Institute of Organic Chemistry of the National Academy of Sciences of Ukraine
Ukraine
;
_audit_update_record             
;
2023-12-04 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_audit_creation_date             2022-10-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[3.6]decan-1-one
_chemical_formula_moiety         'C16 H27 B O3'
_chemical_formula_sum            'C16 H27 B O3'
_chemical_formula_weight         278.18
_chemical_melting_point          326
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7371(3)
_cell_length_b                   9.7392(5)
_cell_length_c                   13.4409(6)
_cell_angle_alpha                102.908(3)
_cell_angle_beta                 102.707(3)
_cell_angle_gamma                103.170(3)
_cell_volume                     802.20(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2984
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.14
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.152
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_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
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_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_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2207
_reflns_number_total             2822
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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)'
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.035
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vd53
_database_code_depnum_ccdc_archive 'CCDC 2312011'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;Institute of Organic Chemistry of the National Academy of Sciences of Ukraine
Ukraine
;
_audit_update_record             
;
2023-12-04 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_audit_creation_date             2022-11-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
3-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[3.3]heptan-1-one
_chemical_formula_moiety         'C19 H25 B O3'
_chemical_formula_sum            'C19 H25 B O3'
_chemical_formula_weight         312.20
_chemical_melting_point          352
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.9091(9)
_cell_length_b                   16.369(2)
_cell_length_c                   15.729(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.089(10)
_cell_angle_gamma                90
_cell_volume                     1777.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1540
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      17.92
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1375
_diffrn_reflns_av_unetI/netI     0.1160
_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       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23572
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.796
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_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_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1504
_reflns_number_total             3128
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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)'
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1627
_refine_ls_R_factor_gt           0.0706
_refine_ls_restrained_S_all      1.003
_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)+(0.0294P)²+0.4495P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1608
_refine_special_details          ?
_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 Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.5768(4) 0.06957(17) 0.41489(19) 0.0946(10) Uani 1 1 d . . . . .
O2 O 0.6541(3) 0.31492(13) 0.40736(15) 0.0652(7) Uani 1 1 d . . . . .
O3 O 0.3405(3) 0.35533(14) 0.39042(14) 0.0623(7) Uani 1 1 d . . . . .
C1 C 0.5057(5) 0.1222(2) 0.4573(3) 0.0668(11) Uani 1 1 d . . . . .
C2 C 0.5815(5) 0.1805(2) 0.5243(2) 0.0693(11) Uani 1 1 d . . . . .
H2A H 0.707733 0.203218 0.513159 0.083 Uiso 1 1 calc R U . . .
H2B H 0.577007 0.159622 0.581914 0.083 Uiso 1 1 calc R U . . .
C3 C 0.4068(4) 0.2380(2) 0.4977(2) 0.0509(9) Uani 1 1 d . . . . .
C4 C 0.3080(5) 0.1613(2) 0.4532(2) 0.0510(9) Uani 1 1 d . . . . .
C5 C 0.1596(5) 0.1074(2) 0.4994(2) 0.0610(10) Uani 1 1 d . . . . .
H5A H 0.217787 0.064105 0.533757 0.073 Uiso 1 1 calc R U . . .
H5B H 0.066076 0.138105 0.530988 0.073 Uiso 1 1 calc R U . . .
C6 C 0.0841(6) 0.0795(2) 0.4107(2) 0.0771(12) Uani 1 1 d . . . . .
H6A H 0.139902 0.028516 0.391930 0.092 Uiso 1 1 calc R U . . .
H6B H -0.056028 0.078640 0.404065 0.092 Uiso 1 1 calc R U . . .
C7 C 0.1785(5) 0.1560(2) 0.3736(2) 0.0635(10) Uani 1 1 d . . . . .
H7A H 0.247825 0.145670 0.322171 0.076 Uiso 1 1 calc R U . . .
H7B H 0.090559 0.201849 0.366095 0.076 Uiso 1 1 calc R U . . .
C8 C 0.2975(5) 0.2796(2) 0.5675(2) 0.0509(9) Uani 1 1 d . . . . .
C9 C 0.3818(5) 0.2964(2) 0.6472(3) 0.0661(11) Uani 1 1 d . . . . .
H9 H 0.509169 0.280801 0.659468 0.079 Uiso 1 1 calc R U . . .
C10 C 0.2782(7) 0.3360(2) 0.7085(2) 0.0754(12) Uani 1 1 d . . . . .
H10 H 0.336710 0.346305 0.761583 0.090 Uiso 1 1 calc R U . . .
C11 C 0.0918(7) 0.3603(2) 0.6923(3) 0.0754(12) Uani 1 1 d . . . . .
H11 H 0.023619 0.387058 0.733901 0.090 Uiso 1 1 calc R U . . .
C12 C 0.0052(5) 0.3448(2) 0.6136(3) 0.0666(11) Uani 1 1 d . . . . .
H12 H -0.122250 0.360759 0.602063 0.080 Uiso 1 1 calc R U . . .
C13 C 0.1080(5) 0.3057(2) 0.5518(2) 0.0576(10) Uani 1 1 d . . . . .
H13 H 0.049029 0.296568 0.498590 0.069 Uiso 1 1 calc R U . . .
C14 C 0.6585(5) 0.3920(2) 0.3594(2) 0.0570(10) Uani 1 1 d . . . . .
C15 C 0.4460(5) 0.3991(2) 0.3254(2) 0.0537(9) Uani 1 1 d . . . . .
C16 C 0.7178(6) 0.4575(2) 0.4233(2) 0.0814(12) Uani 1 1 d . . . . .
H16A H 0.624107 0.460277 0.466847 0.122 Uiso 1 1 calc R U . . .
H16B H 0.724345 0.509337 0.395029 0.122 Uiso 1 1 calc R U . . .
H16C H 0.842484 0.444385 0.448642 0.122 Uiso 1 1 calc R U . . .
C17 C 0.8088(6) 0.3845(3) 0.2917(2) 0.0921(14) Uani 1 1 d . . . . .
H17A H 0.934650 0.377207 0.318564 0.138 Uiso 1 1 calc R U . . .
H17B H 0.808193 0.433204 0.257750 0.138 Uiso 1 1 calc R U . . .
H17C H 0.778628 0.338258 0.256065 0.138 Uiso 1 1 calc R U . . .
C18 C 0.3668(5) 0.4855(2) 0.3202(2) 0.0728(11) Uani 1 1 d . . . . .
H18A H 0.234986 0.484191 0.298676 0.109 Uiso 1 1 calc R U . . .
H18B H 0.443408 0.517381 0.282776 0.109 Uiso 1 1 calc R U . . .
H18C H 0.371782 0.509666 0.375868 0.109 Uiso 1 1 calc R U . . .
C19 C 0.4041(6) 0.3552(2) 0.2421(2) 0.0879(13) Uani 1 1 d . . . . .
H19A H 0.452378 0.300325 0.246073 0.132 Uiso 1 1 calc R U . . .
H19B H 0.466593 0.383404 0.197114 0.132 Uiso 1 1 calc R U . . .
H19C H 0.266864 0.354139 0.230239 0.132 Uiso 1 1 calc R U . . .
B1 B 0.4690(6) 0.3037(2) 0.4301(3) 0.0519(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 1.206(4) . ?
O2 C14 1.471(4) . ?
O2 B1 1.353(4) . ?
O3 C15 1.465(3) . ?
O3 B1 1.361(4) . ?
C1 C2 1.501(5) . ?
C1 C4 1.508(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.575(4) . ?
C3 C4 1.579(5) . ?
C3 C8 1.516(4) . ?
C3 B1 1.582(5) . ?
C4 C5 1.553(4) . ?
C4 C7 1.515(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.539(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.537(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.391(4) . ?
C8 C13 1.391(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.363(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.548(5) . ?
C14 C16 1.517(5) . ?
C14 C17 1.519(4) . ?
C15 C18 1.517(4) . ?
C15 C19 1.513(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

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 C14 106.9(3) . . ?
B1 O3 C15 107.0(3) . . ?
O1 C1 C2 134.8(4) . . ?
O1 C1 C4 131.8(4) . . ?
C2 C1 C4 93.0(3) . . ?
C1 C2 H2A 114.1 . . ?
C1 C2 H2B 114.1 . . ?
C1 C2 C3 87.1(3) . . ?
H2A C2 H2B 111.3 . . ?
C3 C2 H2A 114.1 . . ?
C3 C2 H2B 114.1 . . ?
C2 C3 C4 87.6(2) . . ?
C2 C3 B1 111.1(3) . . ?
C4 C3 B1 111.5(3) . . ?
C8 C3 C2 118.2(3) . . ?
C8 C3 C4 117.3(3) . . ?
C8 C3 B1 109.6(3) . . ?
C1 C4 C3 86.7(3) . . ?
C1 C4 C5 110.6(3) . . ?
C1 C4 C7 121.2(3) . . ?
C5 C4 C3 121.8(3) . . ?
C7 C4 C3 130.1(3) . . ?
C7 C4 C5 88.4(3) . . ?
C4 C5 H5A 114.1 . . ?
C4 C5 H5B 114.1 . . ?
H5A C5 H5B 111.3 . . ?
C6 C5 C4 87.3(2) . . ?
C6 C5 H5A 114.1 . . ?
C6 C5 H5B 114.1 . . ?
C5 C6 H6A 114.0 . . ?
C5 C6 H6B 114.0 . . ?
H6A C6 H6B 111.2 . . ?
C7 C6 C5 88.2(3) . . ?
C7 C6 H6A 114.0 . . ?
C7 C6 H6B 114.0 . . ?
C4 C7 C6 88.8(3) . . ?
C4 C7 H7A 113.8 . . ?
C4 C7 H7B 113.8 . . ?
C6 C7 H7A 113.8 . . ?
C6 C7 H7B 113.8 . . ?
H7A C7 H7B 111.1 . . ?
C9 C8 C3 122.6(3) . . ?
C13 C8 C3 120.0(3) . . ?
C13 C8 C9 117.3(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.7(4) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.1(4) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.4(4) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.0(4) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 H13 119.2 . . ?
C12 C13 C8 121.5(3) . . ?
C12 C13 H13 119.2 . . ?
O2 C14 C15 101.8(2) . . ?
O2 C14 C16 106.0(3) . . ?
O2 C14 C17 108.5(3) . . ?
C16 C14 C15 113.9(3) . . ?
C16 C14 C17 110.3(3) . . ?
C17 C14 C15 115.4(3) . . ?
O3 C15 C14 102.2(2) . . ?
O3 C15 C18 107.8(3) . . ?
O3 C15 C19 106.7(3) . . ?
C18 C15 C14 115.1(3) . . ?
C19 C15 C14 114.3(3) . . ?
C19 C15 C18 109.8(3) . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 B1 O3 113.6(3) . . ?
O2 B1 C3 123.6(3) . . ?
O3 B1 C3 122.8(3) . . ?

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 154.4(4) . . . . ?
O1 C1 C4 C3 -154.8(4) . . . . ?
O1 C1 C4 C5 82.3(5) . . . . ?
O1 C1 C4 C7 -18.8(6) . . . . ?
O2 C14 C15 O3 28.4(3) . . . . ?
O2 C14 C15 C18 145.0(3) . . . . ?
O2 C14 C15 C19 -86.5(3) . . . . ?
C1 C2 C3 C4 17.5(2) . . . . ?
C1 C2 C3 C8 137.4(3) . . . . ?
C1 C2 C3 B1 -94.6(3) . . . . ?
C1 C4 C5 C6 -102.7(3) . . . . ?
C1 C4 C7 C6 93.0(3) . . . . ?
C2 C1 C4 C3 18.3(2) . . . . ?
C2 C1 C4 C5 -104.5(3) . . . . ?
C2 C1 C4 C7 154.3(3) . . . . ?
C2 C3 C4 C1 -17.4(2) . . . . ?
C2 C3 C4 C5 94.8(3) . . . . ?
C2 C3 C4 C7 -146.4(3) . . . . ?
C2 C3 C8 C9 25.9(5) . . . . ?
C2 C3 C8 C13 -156.8(3) . . . . ?
C2 C3 B1 O2 -8.0(5) . . . . ?
C2 C3 B1 O3 173.3(3) . . . . ?
C3 C4 C5 C6 158.1(3) . . . . ?
C3 C4 C7 C6 -152.0(3) . . . . ?
C3 C8 C9 C10 178.6(3) . . . . ?
C3 C8 C13 C12 -179.1(3) . . . . ?
C4 C1 C2 C3 -18.3(2) . . . . ?
C4 C3 C8 C9 128.8(3) . . . . ?
C4 C3 C8 C13 -53.9(4) . . . . ?
C4 C3 B1 O2 -103.9(4) . . . . ?
C4 C3 B1 O3 77.3(4) . . . . ?
C4 C5 C6 C7 -19.9(3) . . . . ?
C5 C4 C7 C6 -20.2(3) . . . . ?
C5 C6 C7 C4 20.4(3) . . . . ?
C7 C4 C5 C6 20.2(3) . . . . ?
C8 C3 C4 C1 -138.1(3) . . . . ?
C8 C3 C4 C5 -25.9(4) . . . . ?
C8 C3 C4 C7 92.8(4) . . . . ?
C8 C3 B1 O2 124.5(3) . . . . ?
C8 C3 B1 O3 -54.2(4) . . . . ?
C8 C9 C10 C11 -0.5(6) . . . . ?
C9 C8 C13 C12 -1.6(5) . . . . ?
C9 C10 C11 C12 0.2(6) . . . . ?
C10 C11 C12 C13 -0.5(6) . . . . ?
C11 C12 C13 C8 1.3(5) . . . . ?
C13 C8 C9 C10 1.2(5) . . . . ?
C14 O2 B1 O3 11.5(4) . . . . ?
C14 O2 B1 C3 -167.4(3) . . . . ?
C15 O3 B1 O2 8.2(4) . . . . ?
C15 O3 B1 C3 -172.9(3) . . . . ?
C16 C14 C15 O3 -85.3(3) . . . . ?
C16 C14 C15 C18 31.3(4) . . . . ?
C16 C14 C15 C19 159.8(3) . . . . ?
C17 C14 C15 O3 145.7(3) . . . . ?
C17 C14 C15 C18 -97.7(4) . . . . ?
C17 C14 C15 C19 30.8(4) . . . . ?
B1 O2 C14 C15 -24.6(3) . . . . ?
B1 O2 C14 C16 94.7(3) . . . . ?
B1 O2 C14 C17 -146.8(3) . . . . ?
B1 O3 C15 C14 -22.9(3) . . . . ?
B1 O3 C15 C18 -144.6(3) . . . . ?
B1 O3 C15 C19 97.5(3) . . . . ?
B1 C3 C4 C1 94.3(3) . . . . ?
B1 C3 C4 C5 -153.4(3) . . . . ?
B1 C3 C4 C7 -34.7(4) . . . . ?
B1 C3 C8 C9 -102.8(4) . . . . ?
B1 C3 C8 C13 74.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
