#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:59:53 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178415 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/36/4023688.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_4023688
loop_
_publ_author_name
'Jarrod W. Johnson'
'Darryl P. Evanoff'
'Marc E. Savard'
'Gerald Lange'
'Timothy R. Ramadhar'
'Abdeljalil Assoud'
'Nicholas J. Taylor'
'Gary I. Dmitrienko'
_publ_section_title
;
 Cyclobutanone Mimics of Penicillins: Effects of Substitution
 on Conformation and Hemiketal Stability
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6970
_journal_page_last               6982
_journal_paper_doi               10.1021/jo801274m
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C13 H18 Cl2 O4 S'
_chemical_formula_weight         341.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                92.940(2)
_cell_angle_beta                 104.377(2)
_cell_angle_gamma                101.967(2)
_cell_formula_units_Z            2
_cell_length_a                   6.3646(6)
_cell_length_b                   10.6579(10)
_cell_length_c                   11.9831(11)
_cell_measurement_temperature    373(2)
_cell_volume                     765.74(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      373(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_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  0.0134
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10709
_diffrn_reflns_theta_full        30.08
_diffrn_reflns_theta_max         30.08
_diffrn_reflns_theta_min         3.38
_exptl_absorpt_coefficient_mu    0.569
_exptl_absorpt_correction_T_max  0.9559
_exptl_absorpt_correction_T_min  0.8128
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'APEX II'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         4302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.181
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0227
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0373P)²+0.2263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0739
_reflns_number_gt                4159
_reflns_number_total             4302
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801274m_si_005.cif
_cod_data_source_block           gd_j1_final
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_hydrogen_treatment' value 'Constr' changed to
'constr' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023688
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.19174(16) -0.47746(9) -0.37927(8) 0.01299(17) Uani 1 1 d . . .
H1 H -0.2952 -0.5207 -0.4524 0.016 Uiso 1 1 calc R . .
S2 S 0.03957(4) -0.55115(2) -0.32676(2) 0.01495(7) Uani 1 1 d . . .
C3 C -0.08914(16) -0.63607(9) -0.22156(8) 0.01298(17) Uani 1 1 d . . .
H3 H 0.0263 -0.6549 -0.1579 0.016 Uiso 1 1 calc R . .
C4 C -0.20498(16) -0.53809(9) -0.17588(8) 0.01205(17) Uani 1 1 d . . .
H4 H -0.0918 -0.4748 -0.1177 0.014 Uiso 1 1 calc R . .
C5 C -0.30304(17) -0.46708(9) -0.27729(8) 0.01310(17) Uani 1 1 d . . .
H5 H -0.4662 -0.4887 -0.3020 0.016 Uiso 1 1 calc R . .
C6 C -0.20082(18) -0.32188(10) -0.25946(9) 0.01598(19) Uani 1 1 d . . .
C7 C -0.13030(17) -0.32711(9) -0.37387(8) 0.01380(17) Uani 1 1 d . . .
C8 C -0.37885(17) -0.60486(9) -0.11846(8) 0.01300(17) Uani 1 1 d . . .
O9 O -0.57662(13) -0.63317(8) -0.16207(7) 0.01996(16) Uani 1 1 d . . .
O10 O -0.28116(13) -0.62616(8) -0.01056(6) 0.01764(15) Uani 1 1 d . . .
C11 C -0.4291(2) -0.68711(10) 0.05700(9) 0.0186(2) Uani 1 1 d . . .
H11X H -0.5735 -0.6665 0.0304 0.022 Uiso 1 1 calc R . .
H11Y H -0.3677 -0.6535 0.1380 0.022 Uiso 1 1 calc R . .
C12 C -0.4565(2) -0.83161(11) 0.04477(10) 0.0223(2) Uani 1 1 d . . .
H12X H -0.3142 -0.8521 0.0736 0.033 Uiso 1 1 calc R . .
H12Y H -0.5164 -0.8648 -0.0355 0.033 Uiso 1 1 calc R . .
H12Z H -0.5563 -0.8699 0.0883 0.033 Uiso 1 1 calc R . .
O13 O -0.25051(12) -0.74863(7) -0.26884(7) 0.01493(14) Uani 1 1 d . . .
C14 C -0.18480(18) -0.87284(9) -0.26460(9) 0.01480(18) Uani 1 1 d . . .
C15 C -0.4085(2) -0.96843(10) -0.30755(11) 0.0225(2) Uani 1 1 d . . .
H15X H -0.5002 -0.9576 -0.2567 0.034 Uiso 1 1 calc R . .
H15Y H -0.3859 -1.0547 -0.3086 0.034 Uiso 1 1 calc R . .
H15Z H -0.4807 -0.9533 -0.3844 0.034 Uiso 1 1 calc R . .
C16 C -0.0690(2) -0.89144(11) -0.14088(10) 0.0211(2) Uani 1 1 d . . .
H16X H 0.0770 -0.8354 -0.1178 0.032 Uiso 1 1 calc R . .
H16Y H -0.0566 -0.9795 -0.1374 0.032 Uiso 1 1 calc R . .
H16Z H -0.1545 -0.8711 -0.0896 0.032 Uiso 1 1 calc R . .
C17 C -0.0353(2) -0.88391(11) -0.34414(11) 0.0252(2) Uani 1 1 d . . .
H17X H -0.1083 -0.8694 -0.4211 0.038 Uiso 1 1 calc R . .
H17Y H -0.0057 -0.9686 -0.3454 0.038 Uiso 1 1 calc R . .
H17Z H 0.1025 -0.8206 -0.3161 0.038 Uiso 1 1 calc R . .
O18 O -0.16428(17) -0.23858(8) -0.18229(8) 0.02553(19) Uani 1 1 d . . .
Cl19 Cl -0.32555(4) -0.27115(2) -0.48223(2) 0.01815(7) Uani 1 1 d . . .
Cl20 Cl 0.14409(4) -0.24679(2) -0.36614(2) 0.01901(7) 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
C7 C1 C5 90.05(7) . . ?
C7 C1 S2 115.24(7) . . ?
C5 C1 S2 106.46(6) . . ?
C1 S2 C3 93.24(4) . . ?
O13 C3 C4 108.00(8) . . ?
O13 C3 S2 114.67(7) . . ?
C4 C3 S2 103.94(6) . . ?
C8 C4 C5 112.75(8) . . ?
C8 C4 C3 110.94(8) . . ?
C5 C4 C3 108.23(8) . . ?
C6 C5 C4 113.10(8) . . ?
C6 C5 C1 88.23(7) . . ?
C4 C5 C1 111.95(8) . . ?
O18 C6 C5 134.71(10) . . ?
O18 C6 C7 132.76(10) . . ?
C5 C6 C7 92.02(7) . . ?
C6 C7 C1 87.82(7) . . ?
C6 C7 Cl20 116.09(7) . . ?
C1 C7 Cl20 119.80(7) . . ?
C6 C7 Cl19 108.61(7) . . ?
C1 C7 Cl19 111.08(7) . . ?
Cl20 C7 Cl19 111.18(5) . . ?
O9 C8 O10 124.38(9) . . ?
O9 C8 C4 125.30(9) . . ?
O10 C8 C4 110.31(8) . . ?
C8 O10 C11 116.56(8) . . ?
O10 C11 C12 110.73(9) . . ?
C3 O13 C14 118.86(8) . . ?
O13 C14 C15 101.99(8) . . ?
O13 C14 C17 110.99(8) . . ?
C15 C14 C17 111.47(9) . . ?
O13 C14 C16 111.02(8) . . ?
C15 C14 C16 110.78(9) . . ?
C17 C14 C16 110.36(9) . . ?
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 C7 1.5626(14) . ?
C1 C5 1.5671(14) . ?
C1 S2 1.8029(10) . ?
S2 C3 1.8444(10) . ?
C3 O13 1.3947(12) . ?
C3 C4 1.5475(13) . ?
C4 C8 1.5187(14) . ?
C4 C5 1.5339(13) . ?
C5 C6 1.5307(14) . ?
C6 O18 1.1920(13) . ?
C6 C7 1.5467(14) . ?
C7 Cl20 1.7558(11) . ?
C7 Cl19 1.7809(10) . ?
C8 O9 1.2034(13) . ?
C8 O10 1.3413(12) . ?
O10 C11 1.4637(13) . ?
C11 C12 1.5088(15) . ?
O13 C14 1.4682(11) . ?
C14 C15 1.5203(15) . ?
C14 C17 1.5209(15) . ?
C14 C16 1.5260(15) . ?
