#------------------------------------------------------------------------------
#$Date: 2022-03-30 03:22:27 +0300 (Wed, 30 Mar 2022) $
#$Revision: 274092 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158602.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_7158602
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      hexagonal
_space_group_IT_number           170
_space_group_name_Hall           'P 65'
_space_group_name_H-M_alt        'P 65'
_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                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   11.311(3)
_cell_length_b                   11.311(3)
_cell_length_c                   25.025(16)
_cell_measurement_reflns_used    362
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      16.94
_cell_measurement_theta_min      2.64
_cell_volume                     2773(2)
_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      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0847
_diffrn_reflns_av_unetI/netI     0.0552
_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       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            30833
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.403
_diffrn_reflns_theta_min         2.079
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1159 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3791
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0201P)²+0.7755P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0807
_reflns_Friedel_coverage         0.953
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2854
_reflns_number_total             3791
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00146b2.cif
_cod_data_source_block           1b11[52b]
_cod_database_code               7158602
_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   0.935
_shelx_estimated_absorpt_t_max   0.974
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'
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
S1 S 0.24407(9) 0.68741(10) 0.05749(4) 0.0365(2) Uani 1 1 d . . . . .
O1 O 0.6274(2) 0.9747(3) -0.03077(10) 0.0373(6) Uani 1 1 d . . . . .
O2 O 0.8481(2) 1.1391(3) -0.02938(10) 0.0385(7) Uani 1 1 d . . . . .
O3 O 0.2641(3) 0.5718(3) 0.04450(12) 0.0528(8) Uani 1 1 d . . . . .
N1 N 0.3777(3) 0.8364(3) 0.03829(13) 0.0334(8) Uani 1 1 d . . . . .
N2 N 0.6518(4) 0.7997(4) 0.07810(16) 0.0559(10) Uani 1 1 d . . . . .
C1 C 0.4889(4) 0.9014(4) 0.07633(14) 0.0322(8) Uani 1 1 d . . . . .
C2 C 0.4516(4) 0.9224(4) 0.13336(16) 0.0511(11) Uani 1 1 d . . . . .
H2A H 0.451787 0.857674 0.159928 0.061 Uiso 1 1 calc R U . . .
H2B H 0.366235 0.926413 0.135494 0.061 Uiso 1 1 calc R U . . .
C3 C 0.5825(4) 1.0637(4) 0.13376(16) 0.0508(12) Uani 1 1 d . . . . .
H3A H 0.662483 1.063613 0.149832 0.061 Uiso 1 1 calc R U . . .
H3B H 0.569870 1.137374 0.149004 0.061 Uiso 1 1 calc R U . . .
C4 C 0.5803(4) 1.0592(4) 0.07204(14) 0.0332(9) Uani 1 1 d . . . . .
C5 C 0.5257(4) 1.1428(4) 0.04409(18) 0.0452(11) Uani 1 1 d . . . . .
H5A H 0.482233 1.178648 0.068534 0.054 Uiso 1 1 calc R U . . .
H5B H 0.466544 1.096374 0.012928 0.054 Uiso 1 1 calc R U . . .
C6 C 0.6749(4) 1.2482(4) 0.02921(17) 0.0418(10) Uani 1 1 d . . . . .
H6A H 0.717974 1.327913 0.053493 0.050 Uiso 1 1 calc R U . . .
H6B H 0.687194 1.277516 -0.008631 0.050 Uiso 1 1 calc R U . . .
C7 C 0.7153(3) 1.1379(3) 0.04117(14) 0.0313(8) Uani 1 1 d . . . . .
H7 H 0.798454 1.171271 0.064051 0.038 Uiso 1 1 calc R U . . .
C8 C 0.7214(4) 1.0716(4) -0.00961(14) 0.0300(8) Uani 1 1 d . . . . .
C9 C 0.8732(4) 1.0963(4) -0.08142(16) 0.0399(9) Uani 1 1 d . . . . .
H9 H 0.786886 1.051773 -0.102735 0.048 Uiso 1 1 calc R U . . .
C10 C 0.9216(4) 0.9960(5) -0.07162(18) 0.0526(12) Uani 1 1 d . . . . .
H10A H 1.009633 1.041981 -0.053020 0.079 Uiso 1 1 calc R U . . .
H10B H 0.932155 0.960282 -0.105867 0.079 Uiso 1 1 calc R U . . .
H10C H 0.854563 0.920551 -0.049591 0.079 Uiso 1 1 calc R U . . .
C11 C 0.9771(5) 1.2252(4) -0.1087(2) 0.0660(14) Uani 1 1 d . . . . .
H11A H 0.940698 1.287258 -0.112452 0.099 Uiso 1 1 calc R U . . .
H11B H 0.997408 1.203025 -0.144190 0.099 Uiso 1 1 calc R U . . .
H11C H 1.060899 1.269243 -0.087365 0.099 Uiso 1 1 calc R U . . .
C12 C 0.5776(4) 0.8403(4) 0.07741(15) 0.0374(9) Uani 1 1 d . . . . .
C13 C 0.1183(4) 0.6825(4) 0.00977(15) 0.0363(9) Uani 1 1 d . . . . .
C14 C 0.0915(5) 0.7971(5) 0.0237(2) 0.0616(13) Uani 1 1 d . . . . .
H14A H 0.175146 0.885037 0.018566 0.092 Uiso 1 1 calc R U . . .
H14B H 0.062530 0.788291 0.061138 0.092 Uiso 1 1 calc R U . . .
H14C H 0.019324 0.792246 0.000557 0.092 Uiso 1 1 calc R U . . .
C15 C -0.0077(4) 0.5436(4) 0.01937(19) 0.0532(12) Uani 1 1 d . . . . .
H15A H -0.085396 0.538127 -0.000164 0.080 Uiso 1 1 calc R U . . .
H15B H -0.028549 0.531572 0.057668 0.080 Uiso 1 1 calc R U . . .
H15C H 0.009671 0.471623 0.006786 0.080 Uiso 1 1 calc R U . . .
C16 C 0.1679(4) 0.6911(5) -0.04728(16) 0.0540(12) Uani 1 1 d . . . . .
H16A H 0.094133 0.674162 -0.072158 0.081 Uiso 1 1 calc R U . . .
H16B H 0.195309 0.622314 -0.052724 0.081 Uiso 1 1 calc R U . . .
H16C H 0.246190 0.782188 -0.053773 0.081 Uiso 1 1 calc R U . . .
H1N H 0.401(3) 0.832(3) 0.0079(14) 0.019(10) 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
O3 S1 N1 111.59(17) . . ?
O3 S1 C13 106.92(18) . . ?
N1 S1 C13 98.03(16) . . ?
C8 O2 C9 118.0(3) . . ?
C1 N1 S1 116.1(3) . . ?
N1 C1 C12 113.2(3) . . ?
N1 C1 C2 116.8(3) . . ?
C12 C1 C2 111.0(3) . . ?
N1 C1 C4 116.5(3) . . ?
C12 C1 C4 108.7(3) . . ?
C2 C1 C4 87.9(3) . . ?
C1 C2 C3 88.3(3) . . ?
C2 C3 C4 88.2(3) . . ?
C5 C4 C7 90.2(3) . . ?
C5 C4 C3 116.2(3) . . ?
C7 C4 C3 119.2(3) . . ?
C5 C4 C1 119.8(3) . . ?
C7 C4 C1 126.7(3) . . ?
C3 C4 C1 87.7(3) . . ?
C4 C5 C6 88.0(3) . . ?
C5 C6 C7 88.9(3) . . ?
C8 C7 C4 114.8(3) . . ?
C8 C7 C6 110.2(3) . . ?
C4 C7 C6 87.5(3) . . ?
O1 C8 O2 124.4(3) . . ?
O1 C8 C7 126.1(3) . . ?
O2 C8 C7 109.5(3) . . ?
O2 C9 C11 105.7(3) . . ?
O2 C9 C10 107.9(3) . . ?
C11 C9 C10 113.7(4) . . ?
N2 C12 C1 176.5(4) . . ?
C14 C13 C16 112.9(4) . . ?
C14 C13 C15 111.3(3) . . ?
C16 C13 C15 109.8(4) . . ?
C14 C13 S1 108.0(3) . . ?
C16 C13 S1 110.7(3) . . ?
C15 C13 S1 103.9(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
S1 O3 1.471(3) . ?
S1 N1 1.676(3) . ?
S1 C13 1.837(4) . ?
O1 C8 1.202(4) . ?
O2 C8 1.337(4) . ?
O2 C9 1.466(4) . ?
N1 C1 1.450(4) . ?
N2 C12 1.142(5) . ?
C1 C12 1.475(6) . ?
C1 C2 1.540(5) . ?
C1 C4 1.556(5) . ?
C2 C3 1.543(5) . ?
C3 C4 1.545(5) . ?
C4 C5 1.532(5) . ?
C4 C7 1.537(5) . ?
C5 C6 1.548(5) . ?
C6 C7 1.557(5) . ?
C7 C8 1.495(5) . ?
C9 C11 1.503(5) . ?
C9 C10 1.506(5) . ?
C13 C14 1.512(5) . ?
C13 C16 1.519(5) . ?
C13 C15 1.523(5) . ?
