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#$Date: 2019-10-28 17:49:30 +0200 (Mon, 28 Oct 2019) $
#$Revision: 220167 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/50/4515043.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_4515043
loop_
_publ_author_name
'Melnykov, Kostiantyn P.'
'Artemenko, Artem N.'
'Ivanenko, Bohdan O.'
'Sokolenko, Yevhenii M.'
'Nosik, Pavel S.'
'Ostapchuk, Eugeniy N.'
'Grygorenko, Oleksandr O.'
'Volochnyuk, Dmitriy M.'
'Ryabukhin, Sergey V.'
_publ_section_title
;
 Scalable Synthesis of Biologically Relevant Spirocyclic Pyrrolidines.
;
_journal_issue                   4
_journal_name_full               'ACS omega'
_journal_page_first              7498
_journal_page_last               7515
_journal_paper_doi               10.1021/acsomega.9b00896
_journal_volume                  4
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C8 H15 N O2 S, Cl'
_chemical_formula_sum            'C8 H15 Cl N O2 S'
_chemical_formula_weight         224.72
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2398(18)
_cell_length_b                   8.637(2)
_cell_length_c                   16.178(5)
_cell_measurement_reflns_used    463
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      22.86
_cell_measurement_theta_min      2.52
_cell_volume                     1011.6(5)
_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(1)
_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  0.0600
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11327
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.977
_diffrn_reflns_theta_min         2.518
_exptl_absorpt_coefficient_mu    0.552
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       prizm
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 640 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0402P)²+0.1624P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0840
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1737
_reflns_number_total             1980
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao9b00896_si_002.cif
_cod_data_source_block           xr133
_cod_database_code               4515043
_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   0.874
_shelx_estimated_absorpt_t_max   0.937
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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
CL1 Cl 0.08103(14) 0.93080(11) 0.66229(5) 0.0280(3) Uani 1 1 d . .
S1 S -0.14797(12) 0.44027(12) 0.56443(5) 0.0188(2) Uani 1 1 d . .
C1 C 0.0324(5) 0.3507(4) 0.6189(2) 0.0173(8) Uani 1 1 d . .
H1A H -0.015200 0.314461 0.671463 0.021 Uiso 1 1 calc R U
H1B H 0.072825 0.260756 0.587890 0.021 Uiso 1 1 calc R U
C2 C 0.1994(5) 0.4541(4) 0.6352(2) 0.0171(8) Uani 1 1 d . .
C5 C -0.0324(5) 0.5111(5) 0.4767(2) 0.0234(9) Uani 1 1 d . .
H5A H 0.015325 0.425399 0.444381 0.028 Uiso 1 1 calc R U
H5B H -0.117766 0.569147 0.442374 0.028 Uiso 1 1 calc R U
C3 C 0.2707(5) 0.5292(4) 0.5555(2) 0.0214(9) Uani 1 1 d . .
H3A H 0.368786 0.600734 0.569882 0.026 Uiso 1 1 calc R U
H3B H 0.324475 0.448895 0.521150 0.026 Uiso 1 1 calc R U
C4 C 0.1274(6) 0.6165(4) 0.5040(2) 0.0259(10) Uani 1 1 d . .
H4A H 0.186950 0.659622 0.455502 0.031 Uiso 1 1 calc R U
H4B H 0.078440 0.701665 0.536358 0.031 Uiso 1 1 calc R U
N1 N 0.1485(4) 0.5782(3) 0.69791(16) 0.0169(6) Uani 1 1 d . .
H1C H 0.111250 0.664065 0.672478 0.020 Uiso 1 1 calc R U
H1D H 0.058334 0.545236 0.730901 0.020 Uiso 1 1 calc R U
C6 C 0.3528(6) 0.3632(5) 0.6797(2) 0.0266(9) Uani 1 1 d . .
H6A H 0.307186 0.262418 0.696547 0.032 Uiso 1 1 calc R U
H6B H 0.457084 0.348045 0.642931 0.032 Uiso 1 1 calc R U
C8 C 0.3207(6) 0.6079(5) 0.7464(3) 0.0349(11) Uani 1 1 d . .
H8A H 0.400334 0.680279 0.717512 0.042 Uiso 1 1 calc R U
H8B H 0.291358 0.649938 0.800385 0.042 Uiso 1 1 calc R U
O2 O -0.2144(3) 0.5689(3) 0.61264(15) 0.0261(6) Uani 1 1 d . .
O1 O -0.2796(4) 0.3226(3) 0.54094(16) 0.0284(7) Uani 1 1 d . .
C7 C 0.4110(7) 0.4553(6) 0.7542(3) 0.0553(15) Uani 1 1 d . .
H7A H 0.371830 0.404011 0.804599 0.066 Uiso 1 1 calc R U
H7B H 0.544272 0.466825 0.755485 0.066 Uiso 1 1 calc R U
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'
Cl Cl 0.1484 0.1585 '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
O2 S1 O1 117.70(17)
O2 S1 C1 108.47(16)
O1 S1 C1 108.24(17)
O2 S1 C5 109.13(18)
O1 S1 C5 110.28(17)
C1 S1 C5 101.81(17)
C2 C1 S1 114.8(3)
N1 C2 C1 109.6(3)
N1 C2 C3 110.1(3)
C1 C2 C3 111.6(3)
N1 C2 C6 102.8(3)
C1 C2 C6 110.8(3)
C3 C2 C6 111.5(3)
C4 C5 S1 109.4(2)
C4 C3 C2 116.0(3)
C3 C4 C5 112.1(3)
C8 N1 C2 105.6(3)
C7 C6 C2 107.9(3)
C7 C8 N1 105.1(3)
C8 C7 C6 106.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.440(3)
S1 O1 1.444(3)
S1 C1 1.754(4)
S1 C5 1.758(4)
C1 C2 1.526(5)
C2 N1 1.522(4)
C2 C3 1.533(5)
C2 C6 1.539(5)
C5 C4 1.537(5)
C3 C4 1.528(5)
N1 C8 1.495(5)
C6 C7 1.505(6)
C8 C7 1.477(6)
