#------------------------------------------------------------------------------
#$Date: 2024-01-06 09:30:55 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288762 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/02/1570210.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_1570210
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         '0.5(C18 H16 Cl2 N2 O), 0.5(H2 O)'
_chemical_formula_sum            'C9 H9 Cl N O'
_chemical_formula_weight         182.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2gr9tc
_audit_creation_date             2023-03-21
_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                 103.554(7)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   18.3768(13)
_cell_length_b                   6.9898(4)
_cell_length_c                   27.6891(17)
_cell_measurement_reflns_used    9067
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      30.55
_cell_measurement_theta_min      2.28
_cell_volume                     3457.6(4)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0833
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            29127
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         2.280
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         5031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0719
_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)+(0.0300P)²+11.7087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1447
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3730
_reflns_number_total             5031
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc05121h2.cif
_cod_data_source_block           v123
_cod_depositor_comments
'Adding full bibliography for 1570208--1570213.cif.'
_cod_database_code               1570210
_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   0.955
_shelx_estimated_absorpt_t_min   0.926
_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,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Ternary CH refined with riding coordinates:
 C4(H4), C6(H6)
2.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B)
2.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C17(H17), C18(H18)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1 C 0.57711(13) 0.1180(3) 0.65634(9) 0.0207(5) Uani 1 1 d . . . . .
C2 C 0.52842(14) -0.0579(4) 0.63455(10) 0.0261(5) Uani 1 1 d . . . . .
H2A H 0.522086 -0.076482 0.599096 0.031 Uiso 1 1 calc R U . . .
H2B H 0.541455 -0.175984 0.652932 0.031 Uiso 1 1 calc R U . . .
C3 C 0.52699(16) 0.1305(4) 0.69451(10) 0.0295(6) Uani 1 1 d . . . . .
H3A H 0.539819 0.040737 0.721918 0.035 Uiso 1 1 calc R U . . .
H3B H 0.519490 0.258799 0.705756 0.035 Uiso 1 1 calc R U . . .
C4 C 0.46556(15) 0.0598(4) 0.64943(10) 0.0283(6) Uani 1 1 d . . . . .
H4 H 0.420753 -0.004598 0.654819 0.034 Uiso 1 1 calc R U . . .
C5 C 0.45794(14) 0.2288(4) 0.61351(11) 0.0291(6) Uani 1 1 d . . . . .
H5A H 0.429347 0.332805 0.623105 0.035 Uiso 1 1 calc R U . . .
H5B H 0.435587 0.191019 0.579558 0.035 Uiso 1 1 calc R U . . .
C6 C 0.54216(13) 0.2810(4) 0.62091(9) 0.0212(5) Uani 1 1 d . . . . .
H6 H 0.552016 0.403880 0.638276 0.025 Uiso 1 1 calc R U . . .
C7 C 0.59735(13) 0.4476(3) 0.56121(9) 0.0194(5) Uani 1 1 d . . . . .
C8 C 0.63485(13) 0.4275(3) 0.51849(9) 0.0187(4) Uani 1 1 d . . . . .
C9 C 0.59754(14) 0.3487(4) 0.47342(9) 0.0240(5) Uani 1 1 d . . . . .
H9 H 0.549089 0.302040 0.469357 0.029 Uiso 1 1 calc R U . . .
C10 C 0.63319(16) 0.3403(4) 0.43453(10) 0.0289(6) Uani 1 1 d . . . . .
H10 H 0.609010 0.289490 0.403942 0.035 Uiso 1 1 calc R U . . .
C11 C 0.70524(16) 0.4091(4) 0.44226(10) 0.0303(6) Uani 1 1 d . . . . .
H11 H 0.728929 0.403441 0.416072 0.036 Uiso 1 1 calc R U . . .
C12 C 0.70773(13) 0.4918(3) 0.52202(9) 0.0194(5) Uani 1 1 d . . . . .
C13 C 0.66098(14) 0.1132(4) 0.67181(9) 0.0231(5) Uani 1 1 d . . . . .
C14 C 0.70001(16) 0.2734(4) 0.69291(11) 0.0354(7) Uani 1 1 d . . . . .
H14 H 0.673709 0.383085 0.697372 0.042 Uiso 1 1 calc R U . . .
C15 C 0.77794(17) 0.2739(5) 0.70762(12) 0.0403(7) Uani 1 1 d . . . . .
H15 H 0.803741 0.382387 0.721667 0.048 Uiso 1 1 calc R U . . .
C16 C 0.81559(15) 0.1106(5) 0.70086(10) 0.0318(6) Uani 1 1 d . . . . .
C17 C 0.77892(16) -0.0512(4) 0.68000(10) 0.0326(6) Uani 1 1 d . . . . .
H17 H 0.805632 -0.160432 0.675711 0.039 Uiso 1 1 calc R U . . .
C18 C 0.70086(15) -0.0493(4) 0.66531(10) 0.0268(5) Uani 1 1 d . . . . .
H18 H 0.675414 -0.157914 0.651039 0.032 Uiso 1 1 calc R U . . .
Cl1 Cl 0.76022(4) 0.58193(10) 0.57790(3) 0.03066(16) Uani 1 1 d . . . . .
Cl2 Cl 0.91341(4) 0.11088(14) 0.71861(3) 0.0506(2) Uani 1 1 d . . . . .
N1 N 0.57131(11) 0.2857(3) 0.57617(8) 0.0196(4) Uani 1 1 d . . . . .
N2 N 0.74322(12) 0.4838(3) 0.48564(8) 0.0251(5) Uani 1 1 d . . . . .
O1 O 0.59171(11) 0.6059(3) 0.57937(8) 0.0306(4) Uani 1 1 d . . . . .
O1W O 0.60658(11) 0.9444(3) 0.52766(8) 0.0308(4) Uani 1 1 d G . . . .
H1WA H 0.605901 0.839546 0.543119 0.046 Uiso 1 1 d G U . . .
H1WB H 0.647604 0.941717 0.518481 0.046 Uiso 1 1 d G U . . .
H1 H 0.5822(15) 0.177(4) 0.5641(10) 0.017(7) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
C2 C1 C3 85.97(19) . . ?
C6 C1 C2 102.8(2) . . ?
C6 C1 C3 99.55(19) . . ?
C13 C1 C2 123.5(2) . . ?
C13 C1 C3 122.6(2) . . ?
C13 C1 C6 116.4(2) . . ?
C1 C2 H2A 114.8 . . ?
C1 C2 H2B 114.8 . . ?
H2A C2 H2B 111.9 . . ?
C4 C2 C1 82.79(18) . . ?
C4 C2 H2A 114.8 . . ?
C4 C2 H2B 114.8 . . ?
C1 C3 H3A 114.9 . . ?
C1 C3 H3B 114.9 . . ?
H3A C3 H3B 111.9 . . ?
C4 C3 C1 82.59(18) . . ?
C4 C3 H3A 114.9 . . ?
C4 C3 H3B 114.9 . . ?
C2 C4 C3 86.3(2) . . ?
C2 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C2 101.4(2) . . ?
C5 C4 C3 102.4(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5A 111.9 . . ?
C4 C5 H5B 111.9 . . ?
C4 C5 C6 99.1(2) . . ?
H5A C5 H5B 109.6 . . ?
C6 C5 H5A 111.9 . . ?
C6 C5 H5B 111.9 . . ?
C1 C6 C5 99.40(19) . . ?
C1 C6 H6 109.5 . . ?
C5 C6 H6 109.5 . . ?
N1 C6 C1 112.04(19) . . ?
N1 C6 C5 116.4(2) . . ?
N1 C6 H6 109.5 . . ?
N1 C7 C8 115.3(2) . . ?
O1 C7 C8 120.2(2) . . ?
O1 C7 N1 124.5(2) . . ?
C9 C8 C7 121.4(2) . . ?
C9 C8 C12 117.0(2) . . ?
C12 C8 C7 121.5(2) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.4(2) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 120.8 . . ?
C11 C10 C9 118.5(2) . . ?
C11 C10 H10 120.8 . . ?
C10 C11 H11 118.2 . . ?
N2 C11 C10 123.6(2) . . ?
N2 C11 H11 118.2 . . ?
C8 C12 Cl1 120.18(18) . . ?
N2 C12 C8 124.7(2) . . ?
N2 C12 Cl1 115.03(18) . . ?
C14 C13 C1 119.9(2) . . ?
C14 C13 C18 118.7(2) . . ?
C18 C13 C1 121.4(2) . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.4(3) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 120.8 . . ?
C16 C15 C14 118.4(3) . . ?
C16 C15 H15 120.8 . . ?
C15 C16 C17 122.0(3) . . ?
C15 C16 Cl2 118.6(2) . . ?
C17 C16 Cl2 119.4(2) . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 118.9(3) . . ?
C18 C17 H17 120.5 . . ?
C13 C18 C17 120.6(3) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C6 N1 H1 118.0(18) . . ?
C7 N1 C6 120.8(2) . . ?
C7 N1 H1 119.2(18) . . ?
C12 N2 C11 116.8(2) . . ?
H1WA O1W H1WB 104.5 . . ?
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
C1 C2 1.556(4) . ?
C1 C3 1.559(3) . ?
C1 C6 1.542(3) . ?
C1 C13 1.500(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C4 1.550(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.554(4) . ?
C4 H4 0.9800 . ?
C4 C5 1.529(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.556(3) . ?
C6 H6 0.9800 . ?
C6 N1 1.461(3) . ?
C7 C8 1.509(3) . ?
C7 N1 1.332(3) . ?
C7 O1 1.229(3) . ?
C8 C9 1.389(3) . ?
C8 C12 1.394(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.386(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(4) . ?
C11 H11 0.9300 . ?
C11 N2 1.345(4) . ?
C12 Cl1 1.738(3) . ?
C12 N2 1.323(3) . ?
C13 C14 1.383(4) . ?
C13 C18 1.386(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.394(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.370(4) . ?
C16 C17 1.373(4) . ?
C16 Cl2 1.749(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.396(4) . ?
C18 H18 0.9300 . ?
N1 H1 0.87(3) . ?
O1W H1WA 0.8502 . ?
O1W H1WB 0.8505 . ?
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
C1 C2 C4 C3 -34.73(18) . . . . ?
C1 C2 C4 C5 67.2(2) . . . . ?
C1 C3 C4 C2 34.69(18) . . . . ?
C1 C3 C4 C5 -66.2(2) . . . . ?
C1 C6 N1 C7 -129.6(2) . . . . ?
C1 C13 C14 C15 -179.9(3) . . . . ?
C1 C13 C18 C17 -179.9(2) . . . . ?
C2 C1 C3 C4 -34.56(18) . . . . ?
C2 C1 C6 C5 40.1(2) . . . . ?
C2 C1 C6 N1 -83.5(2) . . . . ?
C2 C1 C13 C14 -177.1(2) . . . . ?
C2 C1 C13 C18 3.1(4) . . . . ?
C2 C4 C5 C6 -47.7(2) . . . . ?
C3 C1 C2 C4 34.64(19) . . . . ?
C3 C1 C6 C5 -47.9(2) . . . . ?
C3 C1 C6 N1 -171.5(2) . . . . ?
C3 C1 C13 C14 -68.3(3) . . . . ?
C3 C1 C13 C18 111.9(3) . . . . ?
C3 C4 C5 C6 41.0(2) . . . . ?
C4 C5 C6 C1 4.2(2) . . . . ?
C4 C5 C6 N1 124.6(2) . . . . ?
C5 C6 N1 C7 117.0(3) . . . . ?
C6 C1 C2 C4 -64.2(2) . . . . ?
C6 C1 C3 C4 67.7(2) . . . . ?
C6 C1 C13 C14 54.2(3) . . . . ?
C6 C1 C13 C18 -125.6(3) . . . . ?
C7 C8 C9 C10 177.3(2) . . . . ?
C7 C8 C12 Cl1 4.8(3) . . . . ?
C7 C8 C12 N2 -177.9(2) . . . . ?
C8 C7 N1 C6 172.4(2) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C8 C12 N2 C11 0.5(4) . . . . ?
C9 C8 C12 Cl1 -176.94(18) . . . . ?
C9 C8 C12 N2 0.4(4) . . . . ?
C9 C10 C11 N2 0.1(4) . . . . ?
C10 C11 N2 C12 -0.7(4) . . . . ?
C12 C8 C9 C10 -1.0(4) . . . . ?
C13 C1 C2 C4 161.6(2) . . . . ?
C13 C1 C3 C4 -162.3(2) . . . . ?
C13 C1 C6 C5 178.2(2) . . . . ?
C13 C1 C6 N1 54.6(3) . . . . ?
C13 C14 C15 C16 -0.2(5) . . . . ?
C14 C13 C18 C17 0.3(4) . . . . ?
C14 C15 C16 C17 0.3(5) . . . . ?
C14 C15 C16 Cl2 179.3(2) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C16 C17 C18 C13 -0.2(4) . . . . ?
C18 C13 C14 C15 -0.1(4) . . . . ?
Cl1 C12 N2 C11 177.89(19) . . . . ?
Cl2 C16 C17 C18 -179.1(2) . . . . ?
N1 C7 C8 C9 57.2(3) . . . . ?
N1 C7 C8 C12 -124.6(2) . . . . ?
O1 C7 C8 C9 -122.0(3) . . . . ?
O1 C7 C8 C12 56.2(3) . . . . ?
O1 C7 N1 C6 -8.5(4) . . . . ?
