#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:59:53 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178415 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/36/4023689.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_4023689
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            'C11 H12 Cl2 O5 S'
_chemical_formula_weight         327.17
_chemical_name_systematic
; 
 ? 
;
_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                 102.039(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6343(6)
_cell_length_b                   20.9581(17)
_cell_length_c                   10.6260(9)
_cell_measurement_temperature    295(2)
_cell_volume                     1445.0(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11763
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Face-indexed analytical'
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0071(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         4208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0572P)²+0.2194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1224
_reflns_number_gt                3222
_reflns_number_total             4208
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801274m_si_006.cif
_cod_data_source_block           gd1335m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Integration' changed
to 'integration' 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_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023689
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 0.2306(3) 0.41233(9) 0.09811(17) 0.0524(4) Uani 1 1 d . . .
H1 H 0.2409 0.4206 0.0089 0.063 Uiso 1 1 calc R . .
S2 S 0.03376(7) 0.45933(2) 0.14855(4) 0.05225(15) Uani 1 1 d . . .
C3 C 0.1878(2) 0.47356(8) 0.30684(16) 0.0435(4) Uani 1 1 d . . .
H3 H 0.1481 0.5138 0.3420 0.052 Uiso 1 1 calc R . .
C4 C 0.4122(3) 0.47627(8) 0.29154(18) 0.0493(4) Uani 1 1 d . . .
H4 H 0.5040 0.4677 0.3747 0.059 Uiso 1 1 calc R . .
C5 C 0.4375(3) 0.42407(8) 0.19661(19) 0.0543(4) Uani 1 1 d . . .
H5 H 0.5536 0.4319 0.1548 0.065 Uiso 1 1 calc R . .
C6 C 0.4300(3) 0.35517(10) 0.2432(2) 0.0626(5) Uani 1 1 d . . .
C7 C 0.2440(3) 0.33974(9) 0.13325(19) 0.0590(5) Uani 1 1 d . . .
C8 C 0.4642(3) 0.54110(9) 0.2421(2) 0.0576(5) Uani 1 1 d . . .
O9 O 0.5560(3) 0.54893(8) 0.15816(19) 0.0911(6) Uani 1 1 d . . .
O10 O 0.3999(2) 0.58791(7) 0.30870(15) 0.0685(4) Uani 1 1 d . . .
C11 C 0.4233(4) 0.65326(10) 0.2656(3) 0.0808(7) Uani 1 1 d . . .
H11X H 0.5498 0.6567 0.2340 0.097 Uiso 1 1 calc R . .
H11Y H 0.4325 0.6823 0.3377 0.097 Uiso 1 1 calc R . .
C12 C 0.2480(4) 0.67120(13) 0.1633(3) 0.0962(8) Uani 1 1 d . . .
H12X H 0.2498 0.6462 0.0878 0.144 Uiso 1 1 calc R . .
H12Y H 0.2575 0.7156 0.1435 0.144 Uiso 1 1 calc R . .
H12Z H 0.1218 0.6635 0.1916 0.144 Uiso 1 1 calc R . .
O13 O 0.17889(17) 0.42159(6) 0.39435(11) 0.0469(3) Uani 1 1 d . . .
C14 C 0.0028(3) 0.41734(8) 0.43909(16) 0.0472(4) Uani 1 1 d . . .
O15 O -0.13635(19) 0.45445(7) 0.40969(13) 0.0580(3) Uani 1 1 d . . .
C16 C 0.0072(4) 0.36215(12) 0.5277(2) 0.0759(6) Uani 1 1 d . . .
H16X H 0.0596 0.3758 0.6147 0.114 Uiso 1 1 calc R . .
H16Y H 0.0947 0.3294 0.5055 0.114 Uiso 1 1 calc R . .
H16Z H -0.1299 0.3457 0.5202 0.114 Uiso 1 1 calc R . .
O17 O 0.5222(3) 0.32430(8) 0.32968(19) 0.0894(5) Uani 1 1 d . . .
Cl18 Cl 0.03481(10) 0.30164(3) 0.17881(6) 0.0779(2) Uani 1 1 d . . .
Cl19 Cl 0.33062(13) 0.29406(3) 0.01328(7) 0.0868(2) 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 89.71(14) . . ?
C5 C1 S2 107.72(12) . . ?
C7 C1 S2 117.94(12) . . ?
C3 S2 C1 93.61(8) . . ?
O13 C3 C4 105.56(13) . . ?
O13 C3 S2 112.67(11) . . ?
C4 C3 S2 106.36(12) . . ?
C5 C4 C8 110.41(15) . . ?
C5 C4 C3 106.74(15) . . ?
C8 C4 C3 111.42(15) . . ?
C4 C5 C6 116.65(16) . . ?
C4 C5 C1 110.75(14) . . ?
C6 C5 C1 89.14(15) . . ?
O17 C6 C5 136.0(2) . . ?
O17 C6 C7 132.4(2) . . ?
C5 C6 C7 91.57(16) . . ?
C6 C7 C1 88.49(15) . . ?
C6 C7 Cl18 116.06(14) . . ?
C1 C7 Cl18 119.97(14) . . ?
C6 C7 Cl19 109.09(14) . . ?
C1 C7 Cl19 111.24(12) . . ?
Cl18 C7 Cl19 110.15(11) . . ?
O9 C8 O10 124.54(19) . . ?
O9 C8 C4 124.72(18) . . ?
O10 C8 C4 110.70(16) . . ?
C8 O10 C11 117.20(17) . . ?
O10 C11 C12 110.7(2) . . ?
C14 O13 C3 115.55(13) . . ?
O15 C14 O13 122.73(16) . . ?
O15 C14 C16 125.60(17) . . ?
O13 C14 C16 111.67(16) . . ?
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 1.565(3) . ?
C1 S2 1.8040(18) . ?
S2 C3 1.8016(17) . ?
C3 O13 1.4415(19) . ?
C3 C4 1.531(2) . ?
C4 C5 1.521(3) . ?
C4 C8 1.522(2) . ?
C5 C6 1.531(3) . ?
C6 O17 1.184(3) . ?
C6 C7 1.546(3) . ?
C7 Cl18 1.754(2) . ?
C7 Cl19 1.7827(19) . ?
C8 O9 1.192(2) . ?
C8 O10 1.331(2) . ?
O10 C11 1.463(3) . ?
C11 C12 1.466(4) . ?
O13 C14 1.3529(19) . ?
C14 O15 1.198(2) . ?
C14 C16 1.488(3) . ?
