#------------------------------------------------------------------------------
#$Date: 2021-06-05 22:29:50 +0300 (Sat, 05 Jun 2021) $
#$Revision: 266176 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158025.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_7158025
loop_
_publ_author_name
'Ilari, Denise'
'Maskri, Sarah'
'Schepmann, Dirk'
'Köhler, Jens'
'Daniliuc, Constantin G.'
'Koch, Oliver'
'Wünsch, Bernhard'
_publ_section_title
;
 Diastereoselective synthesis of conformationally restricted KOR agonists.
;
_journal_issue                   18
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4082
_journal_page_last               4099
_journal_paper_doi               10.1039/d1ob00398d
_journal_volume                  19
_journal_year                    2021
_chemical_formula_sum            'C19 H26 N2 O4 S'
_chemical_formula_weight         378.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           'APEX3 v2016.1-0'
_audit_update_record
;
2021-02-16 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                97.4750(10)
_cell_angle_beta                 95.7110(10)
_cell_angle_gamma                98.3790(10)
_cell_formula_units_Z            2
_cell_length_a                   8.5936(2)
_cell_length_b                   9.1593(2)
_cell_length_c                   11.8002(3)
_cell_measurement_reflns_used    7670
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.8751
_cell_measurement_theta_min      3.8059
_cell_volume                     904.42(4)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10832
_diffrn_reflns_theta_full        66.87
_diffrn_reflns_theta_max         66.87
_diffrn_reflns_theta_min         3.81
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.826
_exptl_absorpt_correction_T_max  0.73
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.399
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0325
_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)+(0.0431P)²+0.5103P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0842
_reflns_number_gt                3057
_reflns_number_total             3169
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00398d2.cif
_cod_data_source_block           dan9504
_cod_depositor_comments          'Adding full bibliography for 7158025.cif.'
_cod_database_code               7158025
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.59310(4) 0.83004(4) 0.27026(3) 0.01429(12) Uani d . . . 1 . .
N N1 0.79795(14) 0.25778(13) 0.04079(10) 0.0147(3) Uani d . . . 1 . .
N N2 0.46853(14) 0.67252(13) 0.25289(10) 0.0148(3) Uani d . . . 1 . .
O O1 0.63203(12) 0.32374(11) 0.16205(9) 0.0164(2) Uani d . . . 1 . .
O O2 0.86128(12) 0.48264(11) 0.15678(9) 0.0176(2) Uani d . . . 1 . .
O O3 0.66913(12) 0.83227(11) 0.16768(9) 0.0188(2) Uani d . . . 1 . .
O O4 0.50508(13) 0.94630(11) 0.30551(9) 0.0208(2) Uani d . . . 1 . .
C C1 0.50021(17) 0.54004(16) 0.17789(12) 0.0142(3) Uani d . . . 1 . .
H H1 0.5613 0.5692 0.1143 0.017 Uiso calc U . R 1 . .
C C3 0.38365(18) 0.64433(17) 0.35282(12) 0.0178(3) Uani d . . . 1 . .
H H3A 0.3448 0.7361 0.3841 0.021 Uiso calc U . R 1 . .
H H3B 0.4574 0.6179 0.414 0.021 Uiso calc U . R 1 . .
C C4 0.24350(17) 0.51733(16) 0.31793(13) 0.0184(3) Uani d . . . 1 . .
H H4A 0.1552 0.5547 0.2762 0.022 Uiso calc U . R 1 . .
H H4B 0.2062 0.4822 0.3879 0.022 Uiso calc U . R 1 . .
C C5 0.29042(17) 0.38693(16) 0.24087(12) 0.0157(3) Uani d . . . 1 . .
H H5 0.202 0.3003 0.2229 0.019 Uiso calc U . R 1 . .
C C6 0.44412(17) 0.34097(16) 0.29542(12) 0.0160(3) Uani d . . . 1 . .
H H6A 0.4559 0.366 0.3803 0.019 Uiso calc U . R 1 . .
H H6B 0.4429 0.2325 0.2749 0.019 Uiso calc U . R 1 . .
C C7 0.57994(16) 0.43075(16) 0.24515(12) 0.0142(3) Uani d . . . 1 . .
H H7 0.6674 0.4828 0.3055 0.017 Uiso calc U . R 1 . .
C C8 0.33973(17) 0.44378(16) 0.13088(12) 0.0161(3) Uani d . . . 1 . .
H H8A 0.351 0.3607 0.0711 0.019 Uiso calc U . R 1 . .
H H8B 0.2636 0.5038 0.0991 0.019 Uiso calc U . R 1 . .
C C9 0.77249(16) 0.36493(15) 0.12156(12) 0.0135(3) Uani d . . . 1 . .
C C10 0.68951(17) 0.11601(16) 0.00188(12) 0.0162(3) Uani d . . . 1 . .
H H10A 0.5906 0.1325 -0.0417 0.019 Uiso calc U . R 1 . .
H H10B 0.6627 0.0645 0.0678 0.019 Uiso calc U . R 1 . .
C C11 0.78574(18) 0.02749(17) -0.07534(13) 0.0205(3) Uani d . . . 1 . .
H H11A 0.7158 -0.0393 -0.1388 0.025 Uiso calc U . R 1 . .
H H11B 0.8482 -0.0331 -0.0307 0.025 Uiso calc U . R 1 . .
C C12 0.89433(18) 0.14700(17) -0.12193(13) 0.0204(3) Uani d . . . 1 . .
H H12A 0.8379 0.1829 -0.1875 0.024 Uiso calc U . R 1 . .
H H12B 0.9891 0.1085 -0.1471 0.024 Uiso calc U . R 1 . .
C C13 0.93986(17) 0.27077(16) -0.01895(13) 0.0169(3) Uani d . . . 1 . .
H H13A 1.0336 0.2542 0.0307 0.02 Uiso calc U . R 1 . .
H H13B 0.9623 0.3699 -0.0442 0.02 Uiso calc U . R 1 . .
C C14 0.73856(17) 0.82729(15) 0.38694(12) 0.0142(3) Uani d . . . 1 . .
C C15 0.86537(17) 0.75240(16) 0.36777(12) 0.0163(3) Uani d . . . 1 . .
H H15 0.8752 0.705 0.2929 0.02 Uiso calc U . R 1 . .
C C16 0.97700(17) 0.74820(16) 0.45984(13) 0.0175(3) Uani d . . . 1 . .
H H16 1.0632 0.6962 0.4475 0.021 Uiso calc U . R 1 . .
C C17 0.96611(17) 0.81843(16) 0.57042(12) 0.0161(3) Uani d . . . 1 . .
C C18 0.83854(18) 0.89300(16) 0.58701(12) 0.0168(3) Uani d . . . 1 . .
H H18 0.8296 0.9417 0.6617 0.02 Uiso calc U . R 1 . .
C C19 0.72386(17) 0.89749(15) 0.49627(12) 0.0161(3) Uani d . . . 1 . .
H H19 0.6366 0.9479 0.5088 0.019 Uiso calc U . R 1 . .
C C20 1.08867(18) 0.80960(18) 0.66889(13) 0.0218(3) Uani d . . . 1 . .
H H20A 1.0816 0.8857 0.7339 0.033 Uiso calc U . R 1 . .
H H20B 1.1946 0.8268 0.6442 0.033 Uiso calc U . R 1 . .
H H20C 1.0695 0.7105 0.6926 0.033 Uiso calc U . R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 S1 O4 . . 119.94(6) ?
O3 S1 N2 . . 106.85(6) ?
O4 S1 N2 . . 106.49(6) ?
O3 S1 C14 . . 108.35(7) ?
O4 S1 C14 . . 106.78(7) ?
N2 S1 C14 . . 107.93(6) ?
C9 N1 C13 . . 122.41(12) ?
C9 N1 C10 . . 124.65(12) ?
C13 N1 C10 . . 112.94(11) ?
C3 N2 C1 . . 116.80(11) ?
C3 N2 S1 . . 115.44(9) ?
C1 N2 S1 . . 120.13(9) ?
C9 O1 C7 . . 117.63(11) ?
N2 C1 C8 . . 107.44(11) ?
N2 C1 C7 . . 113.32(11) ?
C8 C1 C7 . . 100.92(11) ?
N2 C1 H1 . . 111.5 ?
C8 C1 H1 . . 111.5 ?
C7 C1 H1 . . 111.5 ?
N2 C3 C4 . . 110.73(12) ?
N2 C3 H3A . . 109.5 ?
C4 C3 H3A . . 109.5 ?
N2 C3 H3B . . 109.5 ?
C4 C3 H3B . . 109.5 ?
H3A C3 H3B . . 108.1 ?
C3 C4 C5 . . 111.07(12) ?
C3 C4 H4A . . 109.4 ?
C5 C4 H4A . . 109.4 ?
C3 C4 H4B . . 109.4 ?
C5 C4 H4B . . 109.4 ?
H4A C4 H4B . . 108.0 ?
C4 C5 C8 . . 107.90(12) ?
C4 C5 C6 . . 110.95(12) ?
C8 C5 C6 . . 103.14(11) ?
C4 C5 H5 . . 111.5 ?
C8 C5 H5 . . 111.5 ?
C6 C5 H5 . . 111.5 ?
C7 C6 C5 . . 105.27(11) ?
C7 C6 H6A . . 110.7 ?
C5 C6 H6A . . 110.7 ?
C7 C6 H6B . . 110.7 ?
C5 C6 H6B . . 110.7 ?
H6A C6 H6B . . 108.8 ?
O1 C7 C6 . . 105.12(11) ?
O1 C7 C1 . . 107.63(11) ?
C6 C7 C1 . . 105.05(11) ?
O1 C7 H7 . . 112.8 ?
C6 C7 H7 . . 112.8 ?
C1 C7 H7 . . 112.8 ?
C1 C8 C5 . . 100.53(11) ?
C1 C8 H8A . . 111.7 ?
C5 C8 H8A . . 111.7 ?
C1 C8 H8B . . 111.7 ?
C5 C8 H8B . . 111.7 ?
H8A C8 H8B . . 109.4 ?
O2 C9 N1 . . 126.12(13) ?
O2 C9 O1 . . 123.92(13) ?
N1 C9 O1 . . 109.96(12) ?
N1 C10 C11 . . 102.80(11) ?
N1 C10 H10A . . 111.2 ?
C11 C10 H10A . . 111.2 ?
N1 C10 H10B . . 111.2 ?
C11 C10 H10B . . 111.2 ?
H10A C10 H10B . . 109.1 ?
C10 C11 C12 . . 104.05(12) ?
C10 C11 H11A . . 110.9 ?
C12 C11 H11A . . 110.9 ?
C10 C11 H11B . . 110.9 ?
C12 C11 H11B . . 110.9 ?
H11A C11 H11B . . 109.0 ?
C11 C12 C13 . . 103.33(12) ?
C11 C12 H12A . . 111.1 ?
C13 C12 H12A . . 111.1 ?
C11 C12 H12B . . 111.1 ?
C13 C12 H12B . . 111.1 ?
H12A C12 H12B . . 109.1 ?
N1 C13 C12 . . 102.58(11) ?
N1 C13 H13A . . 111.2 ?
C12 C13 H13A . . 111.2 ?
N1 C13 H13B . . 111.2 ?
C12 C13 H13B . . 111.2 ?
H13A C13 H13B . . 109.2 ?
C19 C14 C15 . . 120.91(13) ?
C19 C14 S1 . . 119.99(11) ?
C15 C14 S1 . . 119.10(11) ?
C16 C15 C14 . . 118.79(13) ?
C16 C15 H15 . . 120.6 ?
C14 C15 H15 . . 120.6 ?
C15 C16 C17 . . 121.64(14) ?
C15 C16 H16 . . 119.2 ?
C17 C16 H16 . . 119.2 ?
C18 C17 C16 . . 118.34(13) ?
C18 C17 C20 . . 121.51(13) ?
C16 C17 C20 . . 120.13(14) ?
C19 C18 C17 . . 121.16(13) ?
C19 C18 H18 . . 119.4 ?
C17 C18 H18 . . 119.4 ?
C18 C19 C14 . . 119.15(13) ?
C18 C19 H19 . . 120.4 ?
C14 C19 H19 . . 120.4 ?
C17 C20 H20A . . 109.5 ?
C17 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C17 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O3 . 1.4327(11) ?
S1 O4 . 1.4357(11) ?
S1 N2 . 1.6428(12) ?
S1 C14 . 1.7704(14) ?
N1 C9 . 1.3342(19) ?
N1 C13 . 1.4659(18) ?
N1 C10 . 1.4739(18) ?
N2 C3 . 1.4781(18) ?
N2 C1 . 1.4814(18) ?
O1 C9 . 1.3626(17) ?
O1 C7 . 1.4449(17) ?
O2 C9 . 1.2239(18) ?
C1 C8 . 1.5340(19) ?
C1 C7 . 1.5492(19) ?
C1 H1 . 1.0 ?
C3 C4 . 1.530(2) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.532(2) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 C8 . 1.535(2) ?
C5 C6 . 1.549(2) ?
C5 H5 . 1.0 ?
C6 C7 . 1.5412(19) ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 H7 . 1.0 ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C10 C11 . 1.525(2) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 C12 . 1.527(2) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C13 . 1.527(2) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C19 . 1.391(2) ?
C14 C15 . 1.391(2) ?
C15 C16 . 1.384(2) ?
C15 H15 . 0.95 ?
C16 C17 . 1.396(2) ?
C16 H16 . 0.95 ?
C17 C18 . 1.390(2) ?
C17 C20 . 1.507(2) ?
C18 C19 . 1.390(2) ?
C18 H18 . 0.95 ?
C19 H19 . 0.95 ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O3 S1 N2 C3 . . . . 176.70(10) ?
O4 S1 N2 C3 . . . . -53.99(11) ?
C14 S1 N2 C3 . . . . 60.36(11) ?
O3 S1 N2 C1 . . . . 28.11(12) ?
O4 S1 N2 C1 . . . . 157.42(10) ?
C14 S1 N2 C1 . . . . -88.23(11) ?
C3 N2 C1 C8 . . . . 59.55(15) ?
S1 N2 C1 C8 . . . . -152.28(10) ?
C3 N2 C1 C7 . . . . -51.04(16) ?
S1 N2 C1 C7 . . . . 97.14(13) ?
C1 N2 C3 C4 . . . . -44.52(16) ?
S1 N2 C3 C4 . . . . 165.81(10) ?
N2 C3 C4 C5 . . . . 44.12(16) ?
C3 C4 C5 C8 . . . . -61.83(15) ?
C3 C4 C5 C6 . . . . 50.47(16) ?
C4 C5 C6 C7 . . . . -92.56(13) ?
C8 C5 C6 C7 . . . . 22.74(14) ?
C9 O1 C7 C6 . . . . -166.53(11) ?
C9 O1 C7 C1 . . . . 81.87(14) ?
C5 C6 C7 O1 . . . . -105.69(12) ?
C5 C6 C7 C1 . . . . 7.73(14) ?
N2 C1 C7 O1 . . . . -168.98(11) ?
C8 C1 C7 O1 . . . . 76.47(12) ?
N2 C1 C7 C6 . . . . 79.37(14) ?
C8 C1 C7 C6 . . . . -35.18(13) ?
N2 C1 C8 C5 . . . . -69.74(13) ?
C7 C1 C8 C5 . . . . 49.16(13) ?
C4 C5 C8 C1 . . . . 72.74(13) ?
C6 C5 C8 C1 . . . . -44.72(13) ?
C13 N1 C9 O2 . . . . -1.2(2) ?
C10 N1 C9 O2 . . . . 178.85(13) ?
C13 N1 C9 O1 . . . . 179.81(11) ?
C10 N1 C9 O1 . . . . -0.11(18) ?
C7 O1 C9 O2 . . . . 4.93(19) ?
C7 O1 C9 N1 . . . . -176.08(11) ?
C9 N1 C10 C11 . . . . -171.61(13) ?
C13 N1 C10 C11 . . . . 8.46(15) ?
N1 C10 C11 C12 . . . . -28.56(14) ?
C10 C11 C12 C13 . . . . 38.28(15) ?
C9 N1 C13 C12 . . . . -164.90(13) ?
C10 N1 C13 C12 . . . . 15.02(15) ?
C11 C12 C13 N1 . . . . -32.22(14) ?
O3 S1 C14 C19 . . . . 147.39(11) ?
O4 S1 C14 C19 . . . . 16.90(13) ?
N2 S1 C14 C19 . . . . -97.25(12) ?
O3 S1 C14 C15 . . . . -33.56(13) ?
O4 S1 C14 C15 . . . . -164.05(11) ?
N2 S1 C14 C15 . . . . 81.80(12) ?
C19 C14 C15 C16 . . . . 0.3(2) ?
S1 C14 C15 C16 . . . . -178.75(11) ?
C14 C15 C16 C17 . . . . -0.7(2) ?
C15 C16 C17 C18 . . . . 0.5(2) ?
C15 C16 C17 C20 . . . . 179.13(13) ?
C16 C17 C18 C19 . . . . 0.3(2) ?
C20 C17 C18 C19 . . . . -178.38(13) ?
C17 C18 C19 C14 . . . . -0.7(2) ?
C15 C14 C19 C18 . . . . 0.4(2) ?
S1 C14 C19 C18 . . . . 179.44(11) ?
