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#$Date: 2025-08-20 17:12:52 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301832 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/19/4101934.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_4101934
loop_
_publ_author_name
'Jarrod W. Johnson'
'Michael Gretes'
'Valerie J. Goodfellow'
'Laura Marrone'
'Miriam L. Heynen'
'Natalie C. J. Strynadka'
'Gary I. Dmitrienko'
_publ_section_title
;
 Cyclobutanone Analogues of β-Lactams Revisited: Insights into
 Conformational Requirements for Inhibition of Serine- and
 Metallo-β-Lactamases
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2558
_journal_page_last               2560
_journal_paper_doi               10.1021/ja9086374
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C8 H8 Cl2 O4 S'
_chemical_formula_weight         271.10
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.413(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.0074(17)
_cell_length_b                   9.2141(13)
_cell_length_c                   10.8132(16)
_cell_measurement_temperature    200(2)
_cell_volume                     1106.0(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11393
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    0.765
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_correction_T_min  0.8143
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'APEX II'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.298
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         3193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.165
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0138P)²+0.5204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0819
_reflns_number_gt                2375
_reflns_number_total             3193
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9086374_si_004.cif
_cod_data_source_block           jj05_888b_0ma
_cod_database_code               4101934
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.70790(18) 0.0563(2) -0.03969(19) 0.0296(4) Uani 1 1 d . . .
H1A H -0.6878 0.1530 -0.0679 0.036 Uiso 1 1 calc R . .
S2 S -0.65628(5) -0.09265(7) -0.11091(5) 0.03640(14) Uani 1 1 d . . .
C3 C -0.79065(19) -0.2019(2) -0.13725(19) 0.0294(4) Uani 1 1 d . . .
H3A H -0.8063 -0.2705 -0.2137 0.035 Uiso 1 1 calc R . .
C4 C -0.89388(17) -0.0931(2) -0.16824(18) 0.0259(4) Uani 1 1 d . . .
H4A H -0.9607 -0.1391 -0.1485 0.031 Uiso 1 1 calc R . .
C5 C -0.84589(18) 0.0359(2) -0.07565(18) 0.0268(4) Uani 1 1 d . . .
H5A H -0.8932 0.1267 -0.1104 0.032 Uiso 1 1 calc R . .
C6 C -0.81978(18) 0.0091(2) 0.07208(19) 0.0266(4) Uani 1 1 d . . .
C7 C -0.68655(19) 0.0507(2) 0.11222(19) 0.0308(4) Uani 1 1 d . . .
C8 C -0.94154(18) -0.0471(2) -0.31420(19) 0.0295(4) Uani 1 1 d . . .
O9 O -0.93229(16) 0.07597(17) -0.34917(14) 0.0435(4) Uani 1 1 d . . .
O10 O -0.99268(16) -0.15254(17) -0.39605(15) 0.0457(4) Uani 1 1 d . . .
H10 H -1.018(3) -0.124(4) -0.490(4) 0.105(12) Uiso 1 1 d . . .
O11 O -0.78515(14) -0.27729(16) -0.02165(14) 0.0356(4) Uani 1 1 d . . .
C12 C -0.7032(3) -0.3967(3) 0.0111(2) 0.0532(7) Uani 1 1 d . . .
H12A H -0.7040 -0.4454 0.0913 0.080 Uiso 1 1 calc R . .
H12B H -0.7275 -0.4655 -0.0636 0.080 Uiso 1 1 calc R . .
H12C H -0.6217 -0.3611 0.0281 0.080 Uiso 1 1 calc R . .
Cl13 Cl -0.66716(7) 0.22938(7) 0.18113(6) 0.05359(19) Uani 1 1 d . . .
Cl14 Cl -0.57993(5) -0.06830(7) 0.21986(5) 0.04454(16) Uani 1 1 d . . .
O15 O -0.87695(13) -0.02773(17) 0.13557(14) 0.0357(4) Uani 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C1 C7 89.48(14) . . ?
C5 C1 S2 107.92(13) . . ?
C7 C1 S2 118.66(14) . . ?
C5 C1 H1A 112.8 . . ?
C7 C1 H1A 112.8 . . ?
S2 C1 H1A 112.8 . . ?
C1 S2 C3 93.41(9) . . ?
O11 C3 C4 106.11(16) . . ?
O11 C3 S2 113.13(14) . . ?
C4 C3 S2 105.44(14) . . ?
O11 C3 H3A 110.6 . . ?
C4 C3 H3A 110.6 . . ?
S2 C3 H3A 110.6 . . ?
C5 C4 C8 111.37(16) . . ?
C5 C4 C3 107.26(16) . . ?
C8 C4 C3 111.31(16) . . ?
C5 C4 H4A 108.9 . . ?
C8 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C4 C5 C6 116.00(16) . . ?
C4 C5 C1 110.99(16) . . ?
C6 C5 C1 89.08(14) . . ?
C4 C5 H5A 112.9 . . ?
C6 C5 H5A 112.9 . . ?
C1 C5 H5A 112.9 . . ?
O15 C6 C5 135.75(19) . . ?
O15 C6 C7 132.44(18) . . ?
C5 C6 C7 91.81(15) . . ?
C6 C7 C1 88.60(14) . . ?
C6 C7 Cl14 116.78(15) . . ?
C1 C7 Cl14 120.35(15) . . ?
C6 C7 Cl13 107.67(14) . . ?
C1 C7 Cl13 110.52(14) . . ?
Cl14 C7 Cl13 110.75(11) . . ?
O9 C8 O10 124.18(18) . . ?
O9 C8 C4 122.76(18) . . ?
O10 C8 C4 113.07(17) . . ?
C8 O10 H10 113(2) . . ?
C3 O11 C12 113.23(16) . . ?
O11 C12 H12A 109.5 . . ?
O11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
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 C5 1.562(3) . ?
C1 C7 1.564(3) . ?
C1 S2 1.796(2) . ?
C1 H1A 1.0000 . ?
S2 C3 1.830(2) . ?
C3 O11 1.409(2) . ?
C3 C4 1.529(3) . ?
C3 H3A 1.0000 . ?
C4 C5 1.519(3) . ?
C4 C8 1.520(3) . ?
C4 H4A 1.0000 . ?
C5 C6 1.526(3) . ?
C5 H5A 1.0000 . ?
C6 O15 1.190(2) . ?
C6 C7 1.538(3) . ?
C7 Cl14 1.749(2) . ?
C7 Cl13 1.786(2) . ?
C8 O9 1.214(2) . ?
C8 O10 1.300(2) . ?
O10 H10 0.98(4) . ?
O11 C12 1.428(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 45379053
