#------------------------------------------------------------------------------
#$Date: 2024-01-06 09:30:55 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288762 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/02/1570213.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1570213
loop_
_publ_author_name
'Denisenko, Aleksandr'
'Garbuz, Pavel'
'Makovetska, Yelyzaveta'
'Shablykin, Oleh'
'Lesyk, Dmytro'
'Al-Maali, Galeb'
'Korzh, Rodion'
'Sadkova, Iryna V.'
'Mykhailiuk, Pavel K.'
_publ_section_title
;
 1,2-Disubstituted bicyclo[2.1.1]hexanes as saturated bioisosteres of
 ortho-substituted benzene.
;
_journal_issue                   48
_journal_name_full               'Chemical science'
_journal_page_first              14092
_journal_page_last               14099
_journal_paper_doi               10.1039/d3sc05121h
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C13 H13 F O2'
_chemical_formula_sum            'C13 H13 F O2'
_chemical_formula_weight         220.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2gr9xg
_audit_creation_date             2022-12-12
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-08-03 deposited with the CCDC.	2023-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.886(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2300(9)
_cell_length_b                   6.3052(5)
_cell_length_c                   14.0798(10)
_cell_measurement_reflns_used    1457
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      19.03
_cell_measurement_theta_min      2.19
_cell_volume                     1085.60(14)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15155
_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         2.189
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       plate
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1917
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0479
_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)+(0.0347P)²+0.2835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.1066
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1207
_reflns_number_total             1917
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc05121h2.cif
_cod_data_source_block           v75
_cod_depositor_comments
'Adding full bibliography for 1570208--1570213.cif.'
_cod_database_code               1570213
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
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'
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
F1 F 0.92187(12) 0.7695(3) 0.15110(10) 0.0867(6) Uani 1 1 d . . . . .
O1 O 0.61347(12) 0.9519(3) 0.56672(11) 0.0562(5) Uani 1 1 d . . . . .
O2 O 0.54345(13) 0.7513(3) 0.45098(11) 0.0556(5) Uani 1 1 d . . . . .
H2 H 0.502562 0.853674 0.444966 0.083 Uiso 1 1 calc R U . . .
C1 C 0.67853(17) 0.5933(3) 0.54911(14) 0.0402(6) Uani 1 1 d . . . . .
H1 H 0.649666 0.467096 0.516740 0.048 Uiso 1 1 calc R U . . .
C2 C 0.80283(16) 0.6171(3) 0.52836(14) 0.0383(5) Uani 1 1 d . . . . .
C3 C 0.8474(2) 0.4219(4) 0.58426(16) 0.0560(7) Uani 1 1 d . . . . .
H3A H 0.807080 0.291364 0.573597 0.067 Uiso 1 1 calc R U . . .
H3B H 0.925734 0.400483 0.580318 0.067 Uiso 1 1 calc R U . . .
C4 C 0.8104(2) 0.5528(4) 0.67127(16) 0.0567(7) Uani 1 1 d . . . . .
H4 H 0.843118 0.525714 0.734085 0.068 Uiso 1 1 calc R U . . .
C5 C 0.68715(19) 0.5508(4) 0.65811(15) 0.0555(7) Uani 1 1 d . . . . .
H5A H 0.652482 0.662077 0.694461 0.067 Uiso 1 1 calc R U . . .
H5B H 0.655958 0.414678 0.674933 0.067 Uiso 1 1 calc R U . . .
C6 C 0.84408(18) 0.7503(4) 0.61450(15) 0.0502(6) Uani 1 1 d . . . . .
H6A H 0.921942 0.779689 0.615284 0.060 Uiso 1 1 calc R U . . .
H6B H 0.801413 0.876583 0.627242 0.060 Uiso 1 1 calc R U . . .
C7 C 0.60967(16) 0.7820(4) 0.52365(15) 0.0397(5) Uani 1 1 d . . . . .
C8 C 0.83506(16) 0.6608(4) 0.42826(15) 0.0390(5) Uani 1 1 d . . . . .
C9 C 0.87380(18) 0.8574(4) 0.40019(16) 0.0500(6) Uani 1 1 d . . . . .
H9 H 0.879413 0.966323 0.444515 0.060 Uiso 1 1 calc R U . . .
C10 C 0.90433(19) 0.8944(4) 0.30712(18) 0.0589(7) Uani 1 1 d . . . . .
H10 H 0.930266 1.026588 0.288767 0.071 Uiso 1 1 calc R U . . .
C11 C 0.89553(19) 0.7336(5) 0.24357(17) 0.0559(7) Uani 1 1 d . . . . .
C12 C 0.85925(19) 0.5364(5) 0.26737(17) 0.0600(7) Uani 1 1 d . . . . .
H12 H 0.855090 0.428454 0.222455 0.072 Uiso 1 1 calc R U . . .
C13 C 0.82869(18) 0.5015(4) 0.36066(16) 0.0516(6) Uani 1 1 d . . . . .
H13 H 0.803379 0.368260 0.378134 0.062 Uiso 1 1 calc R U . . .
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'
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'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2023-78z7p 2023
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
C7 O2 H2 109.5 . . ?
C2 C1 H1 109.7 . . ?
C2 C1 C5 98.60(16) . . ?
C5 C1 H1 109.7 . . ?
C7 C1 H1 109.7 . . ?
C7 C1 C2 115.12(17) . . ?
C7 C1 C5 113.65(18) . . ?
C3 C2 C1 99.43(17) . . ?
C6 C2 C1 102.22(16) . . ?
C6 C2 C3 85.74(16) . . ?
C8 C2 C1 117.79(16) . . ?
C8 C2 C3 121.83(18) . . ?
C8 C2 C6 123.34(18) . . ?
C2 C3 H3A 114.8 . . ?
C2 C3 H3B 114.8 . . ?
H3A C3 H3B 111.9 . . ?
C4 C3 C2 82.78(17) . . ?
C4 C3 H3A 114.8 . . ?
C4 C3 H3B 114.8 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 101.59(19) . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C6 102.51(18) . . ?
C6 C4 C3 86.37(17) . . ?
C6 C4 H4 120.0 . . ?
C1 C5 H5A 111.8 . . ?
C1 C5 H5B 111.8 . . ?
C4 C5 C1 99.84(17) . . ?
C4 C5 H5A 111.8 . . ?
C4 C5 H5B 111.8 . . ?
H5A C5 H5B 109.5 . . ?
C2 C6 H6A 114.8 . . ?
C2 C6 H6B 114.8 . . ?
C4 C6 C2 83.20(17) . . ?
C4 C6 H6A 114.8 . . ?
C4 C6 H6B 114.8 . . ?
H6A C6 H6B 111.8 . . ?
O1 C7 O2 122.1(2) . . ?
O1 C7 C1 123.8(2) . . ?
O2 C7 C1 114.1(2) . . ?
C9 C8 C2 122.0(2) . . ?
C13 C8 C2 120.1(2) . . ?
C13 C8 C9 117.9(2) . . ?
C8 C9 H9 119.4 . . ?
C8 C9 C10 121.2(2) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.7 . . ?
C11 C10 C9 118.5(2) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 F1 119.2(3) . . ?
C10 C11 C12 122.9(2) . . ?
C12 C11 F1 117.9(3) . . ?
C11 C12 H12 121.0 . . ?
C11 C12 C13 118.0(2) . . ?
C13 C12 H12 121.0 . . ?
C8 C13 C12 121.5(2) . . ?
C8 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
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
F1 C11 1.365(3) . ?
O1 C7 1.231(2) . ?
O2 H2 0.8200 . ?
O2 C7 1.309(2) . ?
C1 H1 0.9800 . ?
C1 C2 1.560(3) . ?
C1 C5 1.560(3) . ?
C1 C7 1.498(3) . ?
C2 C3 1.555(3) . ?
C2 C6 1.553(3) . ?
C2 C8 1.495(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.550(3) . ?
C4 H4 0.9800 . ?
C4 C5 1.516(3) . ?
C4 C6 1.540(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 C9 1.387(3) . ?
C8 C13 1.385(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.388(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.355(3) . ?
C11 C12 1.364(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(3) . ?
C13 H13 0.9300 . ?
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
F1 C11 C12 C13 -177.75(19) . . . . ?
C1 C2 C3 C4 -67.58(17) . . . . ?
C1 C2 C6 C4 64.38(17) . . . . ?
C1 C2 C8 C9 107.9(2) . . . . ?
C1 C2 C8 C13 -73.3(3) . . . . ?
C2 C1 C5 C4 -1.9(2) . . . . ?
C2 C1 C7 O1 -70.0(3) . . . . ?
C2 C1 C7 O2 110.4(2) . . . . ?
C2 C3 C4 C5 67.61(19) . . . . ?
C2 C3 C4 C6 -34.43(16) . . . . ?
C2 C8 C9 C10 179.4(2) . . . . ?
C2 C8 C13 C12 -179.23(19) . . . . ?
C3 C2 C6 C4 -34.36(16) . . . . ?
C3 C2 C8 C9 -129.0(2) . . . . ?
C3 C2 C8 C13 49.7(3) . . . . ?
C3 C4 C5 C1 -43.1(2) . . . . ?
C3 C4 C6 C2 34.45(16) . . . . ?
C5 C1 C2 C3 46.11(19) . . . . ?
C5 C1 C2 C6 -41.5(2) . . . . ?
C5 C1 C2 C8 179.89(19) . . . . ?
C5 C1 C7 O1 42.7(3) . . . . ?
C5 C1 C7 O2 -137.0(2) . . . . ?
C5 C4 C6 C2 -66.62(18) . . . . ?
C6 C2 C3 C4 34.13(16) . . . . ?
C6 C2 C8 C9 -21.4(3) . . . . ?
C6 C2 C8 C13 157.4(2) . . . . ?
C6 C4 C5 C1 45.7(2) . . . . ?
C7 C1 C2 C3 167.37(18) . . . . ?
C7 C1 C2 C6 79.7(2) . . . . ?
C7 C1 C2 C8 -58.8(3) . . . . ?
C7 C1 C5 C4 -124.3(2) . . . . ?
C8 C2 C3 C4 161.2(2) . . . . ?
C8 C2 C6 C4 -160.1(2) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C8 C13 C12 -0.4(3) . . . . ?
C9 C10 C11 F1 177.9(2) . . . . ?
C9 C10 C11 C12 -0.8(4) . . . . ?
C10 C11 C12 C13 1.0(4) . . . . ?
C11 C12 C13 C8 -0.3(3) . . . . ?
C13 C8 C9 C10 0.6(3) . . . . ?
