#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:18:14 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180256 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/42/7114279.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_7114279
loop_
_publ_author_name
'Guillard, Jér̂ome'
'Meth-Cohn, Otto'
'Rees, Charles W.'
'White, Andrew J. P.'
'Williams, David J.'
_publ_section_title
;
 Direct conversion of macrocyclic furans into macrocyclic isothiazoles
;
_journal_issue                   3
_journal_name_full               'Chemical Communications'
_journal_page_first              232
_journal_paper_doi               10.1039/b110287g
_journal_year                    2002
_chemical_formula_sum            'C28 H30 N2 O4 S2'
_chemical_formula_weight         522.66
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 101.895(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.0015(15)
_cell_length_b                   6.8083(5)
_cell_length_c                   19.5208(13)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.80
_cell_measurement_theta_min      11.21
_cell_volume                     2731.2(3)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            2210
_diffrn_reflns_theta_max         61.98
_diffrn_reflns_theta_min         4.30
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.056
_exptl_absorpt_correction_T_max  0.9499
_exptl_absorpt_correction_T_min  0.7934
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       needles
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.00028(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.051
_refine_ls_goodness_of_fit_obs   1.074
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1976
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_restrained_S_obs      1.074
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_obs          0.0493
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0466P)²+4.3086P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1285
_refine_ls_wR_factor_obs         0.1109
_reflns_number_observed          1687
_reflns_number_total             2148
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b110287g.txt
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+4.3086P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+4.3086P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7114279
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.49770(4) -0.19784(12) 0.92198(5) 0.0543(3) Uani 1 d .
N2 N 0.57110(13) -0.1051(4) 0.9259(2) 0.0530(7) Uani 1 d .
C3 C 0.56641(15) 0.0702(4) 0.89723(14) 0.0384(7) Uani 1 d .
C4 C 0.50192(14) 0.1364(4) 0.87061(14) 0.0374(6) Uani 1 d .
H4A H 0.49165(14) 0.2573(4) 0.84903(14) 0.045 Uiso 1 calc R
C5 C 0.45723(15) 0.0016(4) 0.88052(14) 0.0384(6) Uani 1 d .
C6 C 0.38538(15) -0.0011(4) 0.86538(14) 0.0389(7) Uani 1 d .
O6 O 0.35838(12) -0.1544(3) 0.87456(14) 0.0577(6) Uani 1 d .
C7 C 0.34671(13) 0.1860(4) 0.84303(14) 0.0362(6) Uani 1 d .
C8 C 0.3591(2) 0.3276(5) 0.9061(2) 0.0475(7) Uani 1 d .
H8A H 0.3463(2) 0.2657(5) 0.9453(2) 0.071 Uiso 1 calc R
H8B H 0.3342(2) 0.4454(5) 0.8941(2) 0.071 Uiso 1 calc R
H8C H 0.4045(2) 0.3599(5) 0.9181(2) 0.071 Uiso 1 calc R
C9 C 0.2742(2) 0.1343(6) 0.8241(2) 0.0537(8) Uani 1 d .
H9A H 0.2615(2) 0.0723(6) 0.8634(2) 0.081 Uiso 1 calc R
H9B H 0.2664(2) 0.0463(6) 0.7848(2) 0.081 Uiso 1 calc R
H9C H 0.2492(2) 0.2521(6) 0.8122(2) 0.081 Uiso 1 calc R
C10 C 0.36663(12) 0.2826(4) 0.78192(13) 0.0315(6) Uani 1 d .
O11 O 0.36220(9) 0.1677(3) 0.72331(9) 0.0337(4) Uani 1 d .
C12 C 0.37625(12) 0.2870(4) 0.67128(13) 0.0336(6) Uani 1 d .
C13 C 0.38989(14) 0.4685(4) 0.6969(2) 0.0409(7) Uani 1 d .
H13A H 0.40104(14) 0.5761(4) 0.6725(2) 0.049 Uiso 1 calc R
C14 C 0.38416(15) 0.4663(4) 0.7686(2) 0.0403(7) Uani 1 d .
H14A H 0.39117(15) 0.5711(4) 0.7998(2) 0.048 Uiso 1 calc R
C15 C 0.37218(14) 0.1946(5) 0.60102(14) 0.0387(6) Uani 1 d .
C16 C 0.3101(2) 0.0713(6) 0.5816(2) 0.0590(9) Uani 1 d .
H16A H 0.3080(2) 0.0126(6) 0.5364(2) 0.089 Uiso 1 calc R
H16B H 0.2729(2) 0.1539(6) 0.5802(2) 0.089 Uiso 1 calc R
H16C H 0.3107(2) -0.0300(6) 0.6159(2) 0.089 Uiso 1 calc R
C17 C 0.3718(2) 0.3566(5) 0.5465(2) 0.0526(8) Uani 1 d .
H17A H 0.3691(2) 0.2984(5) 0.5012(2) 0.079 Uiso 1 calc R
H17B H 0.4110(2) 0.4324(5) 0.5587(2) 0.079 Uiso 1 calc R
H17C H 0.3348(2) 0.4406(5) 0.5454(2) 0.079 Uiso 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_3
N2 S1 C5 94.94(14) .
C3 N2 S1 109.9(2) .
N2 C3 C4 115.2(3) .
N2 C3 C15 120.2(3) 2_656
C4 C3 C15 124.4(3) 2_656
C5 C4 C3 111.7(3) .
C4 C5 C6 133.6(3) .
C4 C5 S1 108.2(2) .
C6 C5 S1 118.1(2) .
O6 C6 C5 117.9(3) .
O6 C6 C7 121.4(3) .
C5 C6 C7 120.6(2) .
C10 C7 C6 112.1(2) .
C10 C7 C9 109.6(2) .
C6 C7 C9 108.8(3) .
C10 C7 C8 109.4(2) .
C6 C7 C8 107.5(2) .
C9 C7 C8 109.4(2) .
C14 C10 O11 110.1(2) .
C14 C10 C7 134.2(3) .
O11 C10 C7 115.6(2) .
C10 O11 C12 106.9(2) .
C13 C12 O11 109.2(2) .
C13 C12 C15 134.2(3) .
O11 C12 C15 116.6(2) .
C12 C13 C14 107.5(3) .
C10 C14 C13 106.3(3) .
C12 C15 C16 110.1(2) .
C12 C15 C17 109.0(3) .
C16 C15 C17 109.9(3) .
C12 C15 C3 108.8(2) 2_656
C16 C15 C3 111.7(3) 2_656
C17 C15 C3 107.3(2) 2_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 N2 1.653(3) .
S1 C5 1.714(3) .
N2 C3 1.313(4) .
C3 C4 1.420(4) .
C3 C15 1.538(4) 2_656
C4 C5 1.354(4) .
C5 C6 1.477(4) .
C6 O6 1.219(4) .
C6 C7 1.525(4) .
C7 C10 1.496(4) .
C7 C9 1.533(4) .
C7 C8 1.543(4) .
C10 C14 1.344(4) .
C10 O11 1.373(3) .
O11 C12 1.379(3) .
C12 C13 1.342(4) .
C12 C15 1.495(4) .
C13 C14 1.429(4) .
C15 C16 1.531(4) .
C15 C17 1.531(4) .
C15 C3 1.538(4) 2_656
