#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/89/1518936.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_1518936
loop_
_publ_author_name
'Druzhenko, Tetiana'
'Denisenko, Olexandr'
'Kheylik, Yuri'
'Zozulya, Sergey'
'Shishkina, Svitlana S.'
'Tolmachev, Andrei'
'Mykhailiuk, Pavel K.'
_publ_section_title
;
 Design, Synthesis, and Characterization of SO2-Containing
 Azabicyclo[3.n.1]alkanes: Promising Building Blocks for Drug Discovery.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1922
_journal_page_last               1925
_journal_paper_doi               10.1021/acs.orglett.5b00608
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C18 H24 F N O4 S'
_chemical_formula_sum            'C18 H24 F N O4 S'
_chemical_formula_weight         369.44
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.067(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8882(6)
_cell_length_b                   17.5520(10)
_cell_length_c                   11.4151(8)
_cell_measurement_reflns_used    2967
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3
_cell_measurement_theta_min      3.2
_cell_volume                     1929.9(2)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_molecular_graphics    'XP (Siemens, 1998)'
_computing_publication_material  'SHELXTL (Sheldrick, 1998)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 1998)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  Xcalibur"3
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_sigmaI/netI    0.0470
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            12992
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.9615
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3348
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0617P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1239
_reflns_number_gt                2311
_reflns_number_total             3348
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            8.CIF
_cod_data_source_block           8
_cod_depositor_comments
'Adding full bibliography for 1518936--1518941.cif.'
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1518936
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.12271(6) 0.58956(3) 0.10649(6) 0.0554(2) Uani 1 1 d .
F1 F 0.27331(16) 0.47237(11) 0.44517(13) 0.0899(5) Uani 1 1 d .
O1 O 0.20458(17) 0.65434(9) 0.15492(18) 0.0745(6) Uani 1 1 d .
O2 O 0.04227(17) 0.59398(10) -0.01520(16) 0.0730(5) Uani 1 1 d .
O3 O 0.69660(18) 0.47634(10) 0.14181(16) 0.0685(5) Uani 1 1 d .
O4 O 0.60515(16) 0.42947(8) 0.29228(15) 0.0581(5) Uani 1 1 d .
N1 N 0.53442(17) 0.54176(10) 0.21269(17) 0.0491(5) Uani 1 1 d .
C1 C 0.0130(2) 0.56594(17) 0.2021(3) 0.0697(7) Uani 1 1 d .
H1B H -0.0339 0.6116 0.2199 0.084 Uiso 1 1 calc R
H1A H -0.0572 0.5305 0.1612 0.084 Uiso 1 1 calc R
C2 C 0.0902(3) 0.53095(16) 0.3174(2) 0.0664(7) Uani 1 1 d .
H2 H 0.0462 0.5299 0.3813 0.080 Uiso 1 1 calc R
C3 C 0.2144(2) 0.50178(14) 0.3351(2) 0.0556(6) Uani 1 1 d .
C4 C 0.3096(2) 0.49520(12) 0.2516(2) 0.0466(5) Uani 1 1 d .
H4 H 0.3418 0.4423 0.2556 0.056 Uiso 1 1 calc R
C5 C 0.2315(2) 0.50949(12) 0.1219(2) 0.0472(5) Uani 1 1 d .
H5B H 0.1761 0.4650 0.0926 0.057 Uiso 1 1 calc R
H5A H 0.2983 0.5164 0.0723 0.057 Uiso 1 1 calc R
C6 C 0.4397(2) 0.54556(12) 0.2934(2) 0.0478(6) Uani 1 1 d .
H6B H 0.4108 0.5980 0.2989 0.057 Uiso 1 1 calc R
H6A H 0.4884 0.5295 0.3731 0.057 Uiso 1 1 calc R
C7 C 0.5516(2) 0.60785(13) 0.1412(2) 0.0554(6) Uani 1 1 d .
H7B H 0.4647 0.6358 0.1223 0.066 Uiso 1 1 calc R
H7A H 0.5706 0.5905 0.0658 0.066 Uiso 1 1 calc R
C8 C 0.6657(2) 0.66156(12) 0.2004(2) 0.0496(6) Uani 1 1 d .
C9 C 0.7345(3) 0.65529(17) 0.3186(2) 0.0710(8) Uani 1 1 d .
H9 H 0.7124 0.6158 0.3653 0.085 Uiso 1 1 calc R
C10 C 0.8374(3) 0.7076(2) 0.3695(3) 0.0970(11) Uani 1 1 d .
H10 H 0.8838 0.7028 0.4496 0.116 Uiso 1 1 calc R
C11 C 0.8697(4) 0.7660(2) 0.3014(4) 0.0999(12) Uani 1 1 d .
H11 H 0.9383 0.8008 0.3352 0.120 Uiso 1 1 calc R
C12 C 0.8025(4) 0.77293(18) 0.1856(4) 0.0970(11) Uani 1 1 d .
H12 H 0.8235 0.8132 0.1398 0.116 Uiso 1 1 calc R
C13 C 0.7030(3) 0.72090(15) 0.1347(3) 0.0710(7) Uani 1 1 d .
H13 H 0.6595 0.7257 0.0538 0.085 Uiso 1 1 calc R
C14 C 0.6191(2) 0.48123(13) 0.2097(2) 0.0508(6) Uani 1 1 d .
C15 C 0.6787(2) 0.35572(12) 0.3029(2) 0.0563(6) Uani 1 1 d D
C16 C 0.6411(3) 0.32176(15) 0.4138(3) 0.0826(9) Uani 1 1 d D
H16C H 0.5420 0.3181 0.4010 0.124 Uiso 1 1 calc R
H16B H 0.6764 0.3538 0.4820 0.124 Uiso 1 1 calc R
H16A H 0.6812 0.2719 0.4284 0.124 Uiso 1 1 calc R
C17 C 0.6212(4) 0.30919(16) 0.1915(3) 0.1008(11) Uani 1 1 d D
H17C H 0.6581 0.2584 0.2024 0.151 Uiso 1 1 calc R
H17B H 0.6472 0.3323 0.1236 0.151 Uiso 1 1 calc R
H17A H 0.5219 0.3073 0.1777 0.151 Uiso 1 1 calc R
C18 C 0.8339(2) 0.36752(18) 0.3263(3) 0.0862(9) Uani 1 1 d D
H18C H 0.8805 0.3204 0.3520 0.129 Uiso 1 1 calc R
H18B H 0.8616 0.4053 0.3879 0.129 Uiso 1 1 calc R
H18A H 0.8584 0.3844 0.2537 0.129 Uiso 1 1 calc R
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'
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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 S1 O2 118.09(11)
O1 S1 C1 108.82(13)
O2 S1 C1 109.21(12)
O1 S1 C5 108.47(10)
O2 S1 C5 109.44(11)
C1 S1 C5 101.52(12)
C14 O4 C15 121.70(17)
C14 N1 C7 117.38(18)
C14 N1 C6 122.71(18)
C7 N1 C6 119.57(18)
C2 C1 S1 112.36(17)
C3 C2 C1 124.9(2)
C2 C3 F1 118.9(2)
C2 C3 C4 129.9(2)
F1 C3 C4 111.2(2)
C3 C4 C5 110.70(18)
C3 C4 C6 111.17(19)
C5 C4 C6 114.11(18)
C4 C5 S1 113.14(15)
N1 C6 C4 112.85(18)
N1 C7 C8 114.75(19)
C9 C8 C13 117.4(2)
C9 C8 C7 123.1(2)
C13 C8 C7 119.5(2)
C8 C9 C10 120.7(3)
C11 C10 C9 119.9(3)
C12 C11 C10 120.0(3)
C11 C12 C13 120.3(3)
C12 C13 C8 121.7(3)
O3 C14 O4 125.7(2)
O3 C14 N1 123.7(2)
O4 C14 N1 110.53(19)
O4 C15 C17 108.69(19)
O4 C15 C18 110.87(19)
C17 C15 C18 113.4(2)
O4 C15 C16 101.74(18)
C17 C15 C16 111.9(2)
C18 C15 C16 109.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4323(17)
S1 O2 1.4383(17)
S1 C1 1.753(3)
S1 C5 1.755(2)
F1 C3 1.362(3)
O3 C14 1.210(3)
O4 C14 1.339(3)
O4 C15 1.476(3)
N1 C14 1.358(3)
N1 C7 1.450(3)
N1 C6 1.456(3)
C1 C2 1.496(4)
C2 C3 1.304(3)
C3 C4 1.488(3)
C4 C5 1.528(3)
C4 C6 1.545(3)
C7 C8 1.508(3)
C8 C9 1.371(3)
C8 C13 1.381(3)
C9 C10 1.396(4)
C10 C11 1.367(5)
C11 C12 1.344(4)
C12 C13 1.371(4)
C15 C17 1.510(3)
C15 C18 1.512(3)
C15 C16 1.519(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
O1 S1 C1 C2 -72.2(2)
O2 S1 C1 C2 157.60(18)
C5 S1 C1 C2 42.1(2)
S1 C1 C2 C3 -17.6(4)
C1 C2 C3 F1 179.4(2)
C1 C2 C3 C4 0.0(4)
C2 C3 C4 C5 -14.8(3)
F1 C3 C4 C5 165.87(17)
C2 C3 C4 C6 113.1(3)
F1 C3 C4 C6 -66.2(2)
C3 C4 C5 S1 45.8(2)
C6 C4 C5 S1 -80.5(2)
O1 S1 C5 C4 56.13(19)
O2 S1 C5 C4 -173.75(14)
C1 S1 C5 C4 -58.40(18)
C14 N1 C6 C4 -75.8(3)
C7 N1 C6 C4 111.0(2)
C3 C4 C6 N1 -178.95(18)
C5 C4 C6 N1 -52.9(2)
C14 N1 C7 C8 -83.2(3)
C6 N1 C7 C8 90.3(2)
N1 C7 C8 C9 -9.3(3)
N1 C7 C8 C13 171.7(2)
C13 C8 C9 C10 0.4(4)
C7 C8 C9 C10 -178.6(3)
C8 C9 C10 C11 0.3(5)
C9 C10 C11 C12 0.1(5)
C10 C11 C12 C13 -1.2(5)
C11 C12 C13 C8 2.0(5)
C9 C8 C13 C12 -1.6(4)
C7 C8 C13 C12 177.5(3)
C15 O4 C14 O3 -4.8(3)
C15 O4 C14 N1 175.97(17)
C7 N1 C14 O3 -8.1(3)
C6 N1 C14 O3 178.6(2)
C7 N1 C14 O4 171.17(19)
C6 N1 C14 O4 -2.2(3)
C14 O4 C15 C17 -66.9(3)
C14 O4 C15 C18 58.3(3)
C14 O4 C15 C16 174.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139044803
