#------------------------------------------------------------------------------
#$Date: 2022-03-30 03:22:27 +0300 (Wed, 30 Mar 2022) $
#$Revision: 274092 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/85/7158597.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_7158597
loop_
_publ_author_name
'Chernykh, Anton V.'
'Chernykh, Alla V.'
'Radchenko, Dmytro S.'
'Chheda, Pratik Rajesh'
'Rusanov, Eduard B.'
'Grygorenko, Oleksandr O.'
'Spies, M. Ashley'
'Volochnyuk, Dmitriy M.'
'Komarov, Igor V.'
_publ_section_title
;
 A stereochemical journey around spirocyclic glutamic acid analogs
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00146B
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H26 N2 O3 S'
_chemical_formula_sum            'C16 H26 N2 O3 S'
_chemical_formula_weight         326.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2021-09-08 deposited with the CCDC.	2022-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.358(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.407(3)
_cell_length_b                   6.1109(8)
_cell_length_c                   18.265(2)
_cell_measurement_reflns_used    1344
_cell_measurement_temperature    138(2)
_cell_measurement_theta_max      25.67
_cell_measurement_theta_min      2.21
_cell_volume                     1808.0(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      138(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9459
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.214
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1086 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3160
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0351P)²+0.3452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0715
_refine_ls_wR_factor_ref         0.0739
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    0.865
_reflns_Friedel_fraction_max     0.858
_reflns_number_gt                2877
_reflns_number_total             3160
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00146b2.cif
_cod_data_source_block           platon_sq[50a]
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7158597
_shelx_shelxl_version_number     2016/4
_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.
;
_shelx_estimated_absorpt_t_min   0.907
_shelx_estimated_absorpt_t_max   0.987
_platon_squeeze_void_probe_radius 1.20
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.73201(15) 0.5322(5) 0.82478(16) 0.0223(6) Uani 1 1 d . . . . .
C2 C 0.74808(14) 0.2909(5) 0.81151(14) 0.0245(5) Uani 1 1 d . . . . .
H2A H 0.802402 0.266623 0.814032 0.029 Uiso 1 1 calc R U . . .
H2B H 0.739470 0.187165 0.848300 0.029 Uiso 1 1 calc R U . . .
C3 C 0.67579(14) 0.2982(5) 0.72233(14) 0.0228(5) Uani 1 1 d . . . . .
C4 C 0.67114(17) 0.5490(5) 0.73000(16) 0.0257(6) Uani 1 1 d . . . . .
H4A H 0.615590 0.602541 0.717188 0.031 Uiso 1 1 calc R U . . .
H4B H 0.693357 0.632359 0.698552 0.031 Uiso 1 1 calc R U . . .
C5 C 0.59591(17) 0.1685(5) 0.69539(16) 0.0314(7) Uani 1 1 d . . . . .
H5A H 0.549943 0.256824 0.693453 0.038 Uiso 1 1 calc R U . . .
H5B H 0.603414 0.031868 0.727347 0.038 Uiso 1 1 calc R U . . .
C6 C 0.5907(2) 0.1324(6) 0.60961(18) 0.0417(8) Uani 1 1 d . . . . .
H6A H 0.579739 -0.021240 0.590190 0.050 Uiso 1 1 calc R U . . .
H6B H 0.552417 0.233700 0.566086 0.050 Uiso 1 1 calc R U . . .
C7 C 0.68156(18) 0.1984(5) 0.64678(16) 0.0300(7) Uani 1 1 d . . . . .
H7 H 0.717970 0.066206 0.664024 0.036 Uiso 1 1 calc R U . . .
C8 C 0.70539(18) 0.3528(5) 0.59824(17) 0.0307(7) Uani 1 1 d . . . . .
C9 C 0.81856(19) 0.5145(5) 0.58822(18) 0.0350(7) Uani 1 1 d . . . . .
H9 H 0.776450 0.539452 0.528905 0.042 Uiso 1 1 calc R U . . .
C10 C 0.8937(2) 0.4150(6) 0.5912(2) 0.0500(9) Uani 1 1 d . . . . .
H10A H 0.917298 0.516001 0.566467 0.075 Uiso 1 1 calc R U . . .
H10B H 0.934403 0.386116 0.649207 0.075 Uiso 1 1 calc R U . . .
H10C H 0.878915 0.277309 0.559958 0.075 Uiso 1 1 calc R U . . .
C11 C 0.8353(3) 0.7252(6) 0.6349(2) 0.0634(12) Uani 1 1 d . . . . .
H11A H 0.856928 0.832381 0.610256 0.095 Uiso 1 1 calc R U . . .
H11B H 0.783917 0.780605 0.631736 0.095 Uiso 1 1 calc R U . . .
H11C H 0.875936 0.700753 0.693199 0.095 Uiso 1 1 calc R U . . .
C12 C 0.80455(18) 0.6753(5) 0.85080(17) 0.0283(7) Uani 1 1 d . . . . .
C13 C 0.56236(16) 0.6816(5) 0.89220(16) 0.0270(6) Uani 1 1 d . . . . .
C14 C 0.5185(2) 0.8859(6) 0.8983(2) 0.0464(9) Uani 1 1 d . . . . .
H14A H 0.555822 0.970070 0.947624 0.070 Uiso 1 1 calc R U . . .
H14B H 0.501864 0.975650 0.848426 0.070 Uiso 1 1 calc R U . . .
H14C H 0.469393 0.843610 0.902853 0.070 Uiso 1 1 calc R U . . .
C15 C 0.50657(18) 0.5464(6) 0.81657(18) 0.0427(8) Uani 1 1 d . . . . .
H15A H 0.536329 0.415951 0.814134 0.064 Uiso 1 1 calc R U . . .
H15B H 0.457419 0.501847 0.820562 0.064 Uiso 1 1 calc R U . . .
H15C H 0.489890 0.633887 0.766135 0.064 Uiso 1 1 calc R U . . .
C16 C 0.59574(18) 0.5445(6) 0.97067(18) 0.0394(8) Uani 1 1 d . . . . .
H16A H 0.631578 0.634829 1.018717 0.059 Uiso 1 1 calc R U . . .
H16B H 0.549695 0.488368 0.977946 0.059 Uiso 1 1 calc R U . . .
H16C H 0.627523 0.421504 0.966083 0.059 Uiso 1 1 calc R U . . .
N1 N 0.69152(14) 0.5466(4) 0.87627(15) 0.0230(5) Uani 1 1 d . . . . .
N2 N 0.86024(16) 0.7835(5) 0.86546(16) 0.0464(7) Uani 1 1 d . . . . .
O1 O 0.65678(14) 0.4620(4) 0.54170(14) 0.0553(7) Uani 1 1 d . . . . .
O2 O 0.78626(12) 0.3566(3) 0.62593(11) 0.0344(5) Uani 1 1 d . . . . .
O3 O 0.70048(11) 0.9199(3) 0.94898(11) 0.0321(5) Uani 1 1 d . . . . .
S1 S 0.64681(4) 0.78513(11) 0.87535(4) 0.02245(17) Uani 1 1 d . . . . .
H1N H 0.7216(16) 0.495(4) 0.9230(17) 0.018(8) 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'
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C12 114.8(2) . . ?
N1 C1 C2 110.8(2) . . ?
C12 C1 C2 113.9(2) . . ?
N1 C1 C4 113.3(2) . . ?
C12 C1 C4 112.5(2) . . ?
C2 C1 C4 88.78(19) . . ?
C3 C2 C1 90.3(2) . . ?
C5 C3 C2 122.8(2) . . ?
C5 C3 C4 117.2(2) . . ?
C2 C3 C4 89.4(2) . . ?
C5 C3 C7 88.4(2) . . ?
C2 C3 C7 122.5(2) . . ?
C4 C3 C7 119.9(2) . . ?
C3 C4 C1 89.7(2) . . ?
C3 C5 C6 89.2(2) . . ?
C7 C6 C5 89.1(2) . . ?
C8 C7 C6 118.0(2) . . ?
C8 C7 C3 116.1(2) . . ?
C6 C7 C3 88.7(2) . . ?
O1 C8 O2 124.2(3) . . ?
O1 C8 C7 123.6(3) . . ?
O2 C8 C7 112.2(2) . . ?
O2 C9 C10 106.9(3) . . ?
O2 C9 C11 108.6(2) . . ?
C10 C9 C11 113.3(3) . . ?
N2 C12 C1 175.1(3) . . ?
C15 C13 C14 111.2(3) . . ?
C15 C13 C16 110.8(3) . . ?
C14 C13 C16 112.1(2) . . ?
C15 C13 S1 107.24(18) . . ?
C14 C13 S1 104.6(2) . . ?
C16 C13 S1 110.74(18) . . ?
C1 N1 S1 116.62(19) . . ?
C8 O2 C9 117.7(2) . . ?
O3 S1 N1 111.25(12) . . ?
O3 S1 C13 106.97(11) . . ?
N1 S1 C13 98.63(12) . . ?
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 N1 1.454(3) . ?
C1 C12 1.473(4) . ?
C1 C2 1.545(4) . ?
C1 C4 1.556(4) . ?
C2 C3 1.538(3) . ?
C3 C5 1.531(4) . ?
C3 C4 1.545(4) . ?
C3 C7 1.558(3) . ?
C5 C6 1.540(4) . ?
C6 C7 1.530(4) . ?
C7 C8 1.496(4) . ?
C8 O1 1.198(3) . ?
C8 O2 1.325(3) . ?
C9 O2 1.466(3) . ?
C9 C10 1.488(4) . ?
C9 C11 1.493(4) . ?
C12 N2 1.140(4) . ?
C13 C15 1.516(4) . ?
C13 C14 1.520(4) . ?
C13 C16 1.516(4) . ?
C13 S1 1.835(3) . ?
N1 S1 1.670(3) . ?
O3 S1 1.4834(19) . ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 1.000 0.125 0.500 22 3 ' '
2 0.500 0.625 0.500 22 3 ' '
