Sustainable Synthesis of Thioimidazoles via Carbohydrate-Based Multicomponent Reactions.
Baumann, Marcus; Baxendale, Ian R.; Organic letters 16 (2014) 6076–; doi:10.1021/ol502845h

data_1518306
_publ_section_title
;
 Sustainable Synthesis of Thioimidazoles via Carbohydrate-Based
 Multicomponent Reactions.
;
_journal_issue                   23
_journal_name_full               'Organic letters'
_journal_page_first              6076
_journal_paper_doi               10.1021/ol502845h
_journal_volume                  16
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H22 Cl2 N2 O7 S'
_chemical_formula_sum            'C20 H22 Cl2 N2 O7 S'
_chemical_formula_weight         505.36
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-07-29
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.86783(13)
_cell_length_b                   16.1933(3)
_cell_length_c                   18.4016(3)
_cell_measurement_reflns_used    16807
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      32.7740
_cell_measurement_theta_min      1.7120
_cell_volume                     2344.48(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -13.00   97.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   19.0000  -60.0000 110

  2 omega  -39.00   43.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  -57.0000  -60.0000 82

  3 omega  -40.00   45.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587  -57.0000  120.0000 85

  4 omega   -1.00   99.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000  -30.0000 100

  5 omega   -1.00   97.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000  150.0000 98

  6 omega    0.00   54.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000   60.0000 54

  7 omega   -1.00   56.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   77.0000 -120.0000 57

  8 omega   -3.00   75.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -107.0000   57.5950 78

  9 omega  -18.00   71.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587 -100.0000 -120.0000 89

 10 omega   -9.00   98.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       28.9587   19.0000  120.0000 107
;
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0204274000
_diffrn_orient_matrix_UB_12      0.0306691000
_diffrn_orient_matrix_UB_13      -0.0261114000
_diffrn_orient_matrix_UB_21      0.0856828000
_diffrn_orient_matrix_UB_22      -0.0136199000
_diffrn_orient_matrix_UB_23      -0.0001244000
_diffrn_orient_matrix_UB_31      -0.0191750000
_diffrn_orient_matrix_UB_32      -0.0281649000
_diffrn_orient_matrix_UB_33      -0.0283467000
_diffrn_radiation_collimation    monochromator
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            46370
_diffrn_reflns_theta_full        29.50
_diffrn_reflns_theta_max         29.50
_diffrn_reflns_theta_min         2.21
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'sealed tube'
_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         6525
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.9000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0809
_reflns_number_gt                6159
_reflns_number_total             6525
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502845h_si_002.cif
_cod_data_source_block           14srv171
_cod_depositor_comments
'Adding full bibliography for 1518305--1518306.cif.'
_cod_original_cell_volume        2344.47(7)
_cod_database_code               1518306
_chemical_oxdiff_formula         'C20 H22 Cl2 N2 O7 S1'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.44
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C12A-C13 \\sim C12-C13A
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uiso(H9A) = Uiso(H9C) = Uiso(H9B)
4. Others
 Fixed Sof: O3(0.6) O3A(0.4) C12(0.6) C12A(0.4) C13A(0.4) H13A(0.4) H13B(0.4)
 H13C(0.4) C13(0.6) H13D(0.6) H13E(0.6) H13F(0.6)
5.a Idealised Me refined as rotating group:
 C13A(H13A,H13B,H13C), C13(H13D,H13E,H13F)
;