#------------------------------------------------------------------------------
#$Date: 2020-07-22 02:10:36 +0300 (Wed, 22 Jul 2020) $
#$Revision: 254443 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/85/4038594.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_4038594
loop_
_publ_author_name
'Fujiu, Motohiro'
'Yokoo, Katsuki'
'Aoki, Toshiaki'
'Shibuya, Satoru'
'Sato, Jun'
'Komano, Kazuo'
'Kusano, Hiroki'
'Sato, Soichiro'
'Ogawa, Masayoshi'
'Yamawaki, Kenji'
_publ_section_title
;
 Synthesis of 2-Thio-Substituted 1,6-Diazabicyclo[3.2.1]octane
 Derivatives, Potent β-Lactamase Inhibitors.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00980
_journal_year                    2020
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C14 H18 N2 O3 S'
_chemical_formula_sum            'C14 H18 N2 O3 S'
_chemical_formula_weight         294.36
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-14
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.089(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.2904(10)
_cell_length_b                   6.2175(3)
_cell_length_c                   11.6198(5)
_cell_measurement_reflns_used    6277
_cell_measurement_temperature    100
_cell_measurement_theta_max      73.4320
_cell_measurement_theta_min      3.8700
_cell_volume                     1438.53(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'PLATUS 200K area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     16.00  44.00   0.50    0.50    --    5.00  18.00-150.00   56
  2  ω     50.00  92.00   0.50    0.50    --    5.00  18.00-150.00   84
  3  ω     67.00  92.00   0.50    0.50    --    5.00   0.00-120.00   50
  4  ω   -136.00 -47.00   0.50    0.50    --  -47.20  28.00-180.00  178
  5  ω    -43.00  35.00   0.50    0.50    --  -47.20  28.00-180.00  156
  6  ω   -120.00 -48.00   0.50    0.50    --  -47.20  55.00-120.00  144
  7  ω    -23.00  41.00   0.50    0.50    --  -47.20  55.00-120.00  128
  8  ω   -189.00-117.00   0.50    0.50    -- -100.90  28.00 120.00  144
  9  ω   -173.00-130.00   0.50    0.50    -- -100.90  54.00 174.40   86
 10  ω   -124.00 -87.00   0.50    0.50    -- -100.90  28.00  30.00   74
 11  ω   -185.00 -97.00   0.50    0.50    -- -100.90  28.00-120.00  176
 12  ω   -100.00 -12.00   0.50    0.50    -- -100.90  28.00 120.00  176
 13  ω    -38.00 -13.00   0.50    0.50    -- -100.90  46.00 120.00   50
 14  ω   -189.00 -15.00   0.50    0.50    -- -100.90  55.00-132.50  348
 15  ω   -183.00-148.00   0.50    0.50    -- -100.90  46.00 120.00   70
 16  ω    -48.00 -12.00   0.50    0.50    -- -100.90  46.00 -90.00   72
 17  ω    -39.00 -12.00   0.50    0.50    -- -100.90  37.00-120.00   54
 18  ω   -119.00 -83.00   0.50    0.50    -- -100.90  46.00 120.00   72
 19  ω   -178.00-137.00   0.50    0.50    -- -100.90  37.00-120.00   82
 20  ω   -186.00-153.00   0.50    0.50    -- -100.90  28.00  30.00   66
 21  ω   -138.00 -82.00   0.50    0.50    -- -100.90  46.00 -90.00  112
 22  ω    -52.00 -13.00   0.50    0.50    -- -100.90  28.00  30.00   78
 23  ω    -80.00 -18.00   0.50    0.50    -- -100.90  54.00 174.40  124
 24  ω   -103.00 -11.00   0.50    0.50    -- -100.90  54.00-121.33  184
 25  ω    -55.00 -12.00   0.50    0.50    -- -100.90  28.00-120.00   86
 26  ω   -172.00 -39.00   0.50    0.50    -- -100.90  55.00  95.68  266
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0251200000
_diffrn_orient_matrix_UB_12      0.0027337000
_diffrn_orient_matrix_UB_13      -0.1168548000
_diffrn_orient_matrix_UB_21      0.0208010000
_diffrn_orient_matrix_UB_22      0.2372307000
_diffrn_orient_matrix_UB_23      0.0214226000
_diffrn_orient_matrix_UB_31      0.0701729000
_diffrn_orient_matrix_UB_32      -0.0720140000
_diffrn_orient_matrix_UB_33      0.0641202000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7080
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.965
_diffrn_reflns_theta_min         3.877
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    2.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1166 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_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     182
_refine_ls_number_reflns         2798
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0408P)²+4.2349P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1071
_reflns_Friedel_coverage         0.769
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.922
_reflns_number_gt                2772
_reflns_number_total             2798
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00980_si_001.cif
_cod_data_source_block           x4143r3
_cod_database_code               4038594
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C7 H12 N2 O3 S1'
_chemical_oxdiff_usercomment     -173C
_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_max   0.819
_shelx_estimated_absorpt_t_min   0.705
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C8(H8A,H8B), C7(H7A,H7B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C10(H10), C13(H13), C12(H12), C11(H11)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.199
_oxdiff_exptl_absorpt_empirical_full_min 0.825
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
S1 S 0.33387(4) 0.92311(15) 0.08535(8) 0.0219(2) Uani 1 1 d . . . . .
O3 O 0.60076(13) 0.5379(5) 0.2180(2) 0.0237(6) Uani 1 1 d . . . . .
O2 O 0.55009(12) 0.9334(5) 0.1487(2) 0.0232(5) Uani 1 1 d . . . . .
O1 O 0.28967(13) 0.8084(5) 0.1546(2) 0.0269(6) Uani 1 1 d . . . . .
N2 N 0.54862(15) 0.6317(6) 0.2662(3) 0.0232(7) Uani 1 1 d . . . . .
N1 N 0.45300(15) 0.8299(6) 0.2166(3) 0.0212(7) Uani 1 1 d . . . . .
C6 C 0.52173(18) 0.8120(7) 0.2053(3) 0.0200(8) Uani 1 1 d . . . . .
C2 C 0.41270(18) 0.7720(6) 0.1003(3) 0.0195(8) Uani 1 1 d . . . . .
H2 H 0.437189 0.822558 0.038460 0.023 Uiso 1 1 calc R . . . .
C14 C 0.68820(19) 0.4785(7) 0.5207(4) 0.0258(9) Uani 1 1 d . . . . .
H14 H 0.706832 0.618940 0.531308 0.031 Uiso 1 1 calc R . . . .
C3 C 0.4016(2) 0.5270(7) 0.0861(4) 0.0266(9) Uani 1 1 d . . . . .
H3A H 0.395267 0.490199 0.001764 0.032 Uiso 1 1 calc R . . . .
H3B H 0.359787 0.488203 0.113271 0.032 Uiso 1 1 calc R . . . .
C8 C 0.66341(18) 0.5410(7) 0.3029(4) 0.0242(8) Uani 1 1 d . . . . .
H8A H 0.673777 0.691116 0.328655 0.029 Uiso 1 1 calc R . . . .
H8B H 0.700047 0.489742 0.264599 0.029 Uiso 1 1 calc R . . . .
C9 C 0.66153(17) 0.4043(8) 0.4085(3) 0.0204(8) Uani 1 1 d . . . . .
C10 C 0.6343(2) 0.1980(7) 0.3942(4) 0.0247(8) Uani 1 1 d . . . . .
H10 H 0.616573 0.145314 0.317789 0.030 Uiso 1 1 calc R . . . .
C7 C 0.4455(2) 0.6643(8) 0.3055(4) 0.0272(9) Uani 1 1 d . . . . .
H7A H 0.398383 0.614767 0.296540 0.033 Uiso 1 1 calc R . . . .
H7B H 0.461159 0.717979 0.386342 0.033 Uiso 1 1 calc R . . . .
C13 C 0.6876(2) 0.3472(9) 0.6171(4) 0.0351(11) Uani 1 1 d . . . . .
H13 H 0.706465 0.397566 0.693554 0.042 Uiso 1 1 calc R . . . .
C1 C 0.3025(2) 0.8631(7) -0.0659(3) 0.0279(10) Uani 1 1 d . . . . .
H1A H 0.291009 0.710146 -0.074288 0.042 Uiso 1 1 calc GR . . . .
H1B H 0.337046 0.896571 -0.111687 0.042 Uiso 1 1 calc GR . . . .
H1C H 0.262395 0.949864 -0.094439 0.042 Uiso 1 1 calc GR . . . .
C4 C 0.4603(2) 0.3909(7) 0.1547(4) 0.0304(10) Uani 1 1 d . . . . .
H4A H 0.443736 0.244392 0.166602 0.036 Uiso 1 1 calc R . . . .
H4B H 0.495738 0.378084 0.107274 0.036 Uiso 1 1 calc R . . . .
C5 C 0.4909(2) 0.4883(7) 0.2745(4) 0.0281(10) Uani 1 1 d . . . . .
H5 H 0.502244 0.377403 0.337495 0.034 Uiso 1 1 calc R . . . .
C12 C 0.6596(2) 0.1430(9) 0.6028(4) 0.0374(12) Uani 1 1 d . . . . .
H12 H 0.658907 0.054395 0.669140 0.045 Uiso 1 1 calc R . . . .
C11 C 0.6329(2) 0.0692(8) 0.4913(4) 0.0323(10) Uani 1 1 d . . . . .
H11 H 0.613429 -0.070161 0.481102 0.039 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 0.0181 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C2 107.87(18) . . ?
O1 S1 C1 106.98(18) . . ?
C1 S1 C2 97.19(18) . . ?
N2 O3 C8 110.4(3) . . ?
O3 N2 C5 115.8(3) . . ?
C6 N2 O3 112.5(3) . . ?
C6 N2 C5 106.3(3) . . ?
C6 N1 C2 105.9(3) . . ?
C6 N1 C7 104.1(3) . . ?
C2 N1 C7 110.6(3) . . ?
O2 C6 N2 126.9(4) . . ?
O2 C6 N1 125.0(4) . . ?
N2 C6 N1 108.2(3) . . ?
N1 C2 S1 106.3(3) . . ?
N1 C2 C3 112.4(3) . . ?
C3 C2 S1 112.8(3) . . ?
C13 C14 C9 119.9(4) . . ?
C2 C3 C4 113.6(3) . . ?
O3 C8 C9 113.1(3) . . ?
C14 C9 C8 120.8(4) . . ?
C14 C9 C10 119.4(4) . . ?
C10 C9 C8 119.8(4) . . ?
C11 C10 C9 120.3(4) . . ?
N1 C7 C5 100.7(3) . . ?
C12 C13 C14 120.5(4) . . ?
C5 C4 C3 112.8(4) . . ?
N2 C5 C7 96.0(3) . . ?
N2 C5 C4 111.3(3) . . ?
C7 C5 C4 109.9(3) . . ?
C11 C12 C13 119.6(4) . . ?
C12 C11 C10 120.3(4) . . ?
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 O1 1.496(3) . ?
S1 C2 1.834(4) . ?
S1 C1 1.789(4) . ?
O3 N2 1.414(4) . ?
O3 C8 1.452(4) . ?
O2 C6 1.215(5) . ?
N2 C6 1.381(5) . ?
N2 C5 1.489(5) . ?
N1 C6 1.430(5) . ?
N1 C2 1.483(5) . ?
N1 C7 1.487(5) . ?
C2 C3 1.544(6) . ?
C14 C9 1.391(5) . ?
C14 C13 1.389(6) . ?
C3 C4 1.551(6) . ?
C8 C9 1.499(6) . ?
C9 C10 1.394(6) . ?
C10 C11 1.388(6) . ?
C7 C5 1.519(6) . ?
C13 C12 1.387(8) . ?
C4 C5 1.535(7) . ?
C12 C11 1.383(7) . ?
