#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/14/7201477.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_7201477
loop_
_publ_author_name
'Cohen, Anita'
'Crozet, Maxime D.'
'Rathelot, Pascal'
'Vanelle, Patrice'
_publ_section_title
;
 An efficient aqueous microwave-assisted Suzuki--Miyaura cross-coupling
 reaction in the thiazole series
;
_journal_issue                   11
_journal_name_full               'Green Chemistry'
_journal_page_first              1736
_journal_paper_doi               10.1039/b916123f
_journal_volume                  11
_journal_year                    2009
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H16 F1 N1 O2 S2'
_chemical_formula_sum            'C18 H16 F N O2 S2'
_chemical_formula_weight         361.44
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2009-03-23T14:17:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                111.001(1)
_cell_angle_beta                 103.328(2)
_cell_angle_gamma                103.603(3)
_cell_formula_units_Z            2
_cell_length_a                   8.1330(2)
_cell_length_b                   10.9315(3)
_cell_length_c                   11.3491(4)
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.16
_cell_measurement_theta_min      2.05
_cell_measurement_wavelength     0.71073
_cell_volume                     858.68(5)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.954
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.062
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9942
_diffrn_reflns_theta_full        28.16
_diffrn_reflns_theta_max         28.16
_diffrn_reflns_theta_min         2.05
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.33
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.45
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0772
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0335P)²+3.4066P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2084
_refine_ls_wR_factor_ref         0.2201
_reflns_number_gt                3045
_reflns_number_total             4023
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b916123f.txt
_cod_data_source_block           ac2154
_cod_original_cell_volume        858.68(4)
_cod_database_code               7201477
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
C7 C -0.5373(8) -0.0359(7) 0.2487(8) 0.086(2) Uani 1 1 d . . .
H7A H -0.5586 -0.1238 0.2538 0.129 Uiso 1 1 calc R . .
H7B H -0.5776 -0.0526 0.156 0.129 Uiso 1 1 calc R . .
H7C H -0.6025 0.0146 0.2951 0.129 Uiso 1 1 calc R . .
C9 C 0.1958(6) 0.5249(5) 0.7008(4) 0.0378(9) Uani 1 1 d . . .
C1 C 0.0277(6) 0.2088(5) 0.4366(5) 0.0429(10) Uani 1 1 d . . .
C2 C -0.0646(7) 0.1904(5) 0.3105(5) 0.0495(12) Uani 1 1 d . . .
H2 H -0.0045 0.2318 0.2664 0.059 Uiso 1 1 calc R . .
C3 C -0.2452(7) 0.1112(6) 0.2486(5) 0.0564(13) Uani 1 1 d . . .
H3 H -0.3063 0.0991 0.1628 0.068 Uiso 1 1 calc R . .
C4 C -0.3371(7) 0.0492(5) 0.3135(6) 0.0580(14) Uani 1 1 d . . .
C5 C -0.2423(8) 0.0665(6) 0.4394(7) 0.0681(17) Uani 1 1 d . . .
H5 H -0.3016 0.0241 0.4832 0.082 Uiso 1 1 calc R . .
C6 C -0.0610(7) 0.1457(6) 0.5017(6) 0.0604(14) Uani 1 1 d . . .
H6 H 0.0012 0.1566 0.5867 0.073 Uiso 1 1 calc R . .
C8 C 0.2703(6) 0.4903(5) 0.5894(4) 0.0412(10) Uani 1 1 d . . .
H8A H 0.3954 0.5508 0.6235 0.049 Uiso 1 1 calc R . .
H8B H 0.2046 0.5098 0.5193 0.049 Uiso 1 1 calc R . .
C10 C 0.2882(6) 0.6007(5) 0.8353(4) 0.0379(9) Uani 1 1 d . . .
C11 C 0.4828(6) 0.6762(5) 0.9117(4) 0.0378(9) Uani 1 1 d . . .
C12 C 0.5905(6) 0.7542(5) 0.8667(5) 0.0444(11) Uani 1 1 d . . .
H12 H 0.5394 0.7592 0.7871 0.053 Uiso 1 1 calc R . .
C13 C 0.7733(7) 0.8247(6) 0.9386(5) 0.0538(13) Uani 1 1 d . . .
H13 H 0.8456 0.8763 0.9079 0.065 Uiso 1 1 calc R . .
C14 C 0.8445(6) 0.8165(6) 1.0556(6) 0.0565(14) Uani 1 1 d . . .
C15 C 0.7440(7) 0.7424(6) 1.1051(5) 0.0600(14) Uani 1 1 d . . .
H15 H 0.7965 0.7389 1.1853 0.072 Uiso 1 1 calc R . .
C16 C 0.5616(7) 0.6728(6) 1.0324(5) 0.0490(12) Uani 1 1 d . . .
H16 H 0.4904 0.6228 1.065 0.059 Uiso 1 1 calc R . .
C17 C -0.0410(6) 0.5024(5) 0.7677(5) 0.0451(11) Uani 1 1 d . . .
C18 C -0.2337(6) 0.4563(7) 0.7589(6) 0.0607(15) Uani 1 1 d . . .
H18A H -0.3031 0.485 0.7002 0.091 Uiso 1 1 calc R . .
H18B H -0.2408 0.498 0.8469 0.091 Uiso 1 1 calc R . .
H18C H -0.2807 0.3563 0.724 0.091 Uiso 1 1 calc R . .
F1 F 1.0248(4) 0.8857(4) 1.1271(4) 0.0883(13) Uani 1 1 d . . .
N1 N 0.0104(5) 0.4701(4) 0.6638(4) 0.0420(9) Uani 1 1 d . . .
O1 O 0.3387(5) 0.3006(4) 0.4150(4) 0.0658(11) Uani 1 1 d . . .
O2 O 0.3332(5) 0.2795(4) 0.6250(4) 0.0593(10) Uani 1 1 d . . .
S1 S 0.13473(16) 0.60358(15) 0.91902(12) 0.0487(4) Uani 1 1 d . . .
S2 S 0.25788(15) 0.31253(14) 0.51726(12) 0.0454(3) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
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
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C10 C9 N1 115.7(4) . . ?
C10 C9 C8 128.0(4) . . ?
N1 C9 C8 116.3(4) . . ?
C2 C1 C6 119.8(5) . . ?
C2 C1 S2 120.7(4) . . ?
C6 C1 S2 119.6(4) . . ?
C1 C2 C3 120.6(5) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 120.4(5) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 118.6(5) . . ?
C5 C4 C7 120.0(6) . . ?
C3 C4 C7 121.4(6) . . ?
C6 C5 C4 121.2(6) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 119.5(5) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C9 C8 S2 113.7(3) . . ?
C9 C8 H8A 108.8 . . ?
S2 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
S2 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C9 C10 C11 131.3(4) . . ?
C9 C10 S1 108.6(3) . . ?
C11 C10 S1 120.1(3) . . ?
C12 C11 C16 118.4(4) . . ?
C12 C11 C10 121.1(4) . . ?
C16 C11 C10 120.5(4) . . ?
C13 C12 C11 121.0(5) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 118.3(5) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C13 C14 C15 123.1(5) . . ?
C13 C14 F1 118.6(5) . . ?
C15 C14 F1 118.3(5) . . ?
C14 C15 C16 118.0(5) . . ?
C14 C15 H15 121 . . ?
C16 C15 H15 121 . . ?
C15 C16 C11 121.3(5) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
N1 C17 C18 123.8(5) . . ?
N1 C17 S1 113.7(3) . . ?
C18 C17 S1 122.5(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 N1 C9 111.8(4) . . ?
C17 S1 C10 90.3(2) . . ?
O2 S2 O1 119.0(3) . . ?
O2 S2 C1 108.8(2) . . ?
O1 S2 C1 107.9(2) . . ?
O2 S2 C8 108.2(2) . . ?
O1 S2 C8 105.4(2) . . ?
C1 S2 C8 106.9(2) . . ?
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
C7 C4 1.518(7) . ?
C7 H7A 0.96 . ?
C7 H7B 0.96 . ?
C7 H7C 0.96 . ?
C9 C10 1.361(6) . ?
C9 N1 1.382(5) . ?
C9 C8 1.493(6) . ?
C1 C2 1.372(7) . ?
C1 C6 1.385(7) . ?
C1 S2 1.759(5) . ?
C2 C3 1.375(7) . ?
C2 H2 0.93 . ?
C3 C4 1.391(8) . ?
C3 H3 0.93 . ?
C4 C5 1.380(9) . ?
C5 C6 1.379(7) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C8 S2 1.785(5) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C10 C11 1.475(6) . ?
C10 S1 1.734(4) . ?
C11 C12 1.387(6) . ?
C11 C16 1.390(6) . ?
C12 C13 1.386(6) . ?
C12 H12 0.93 . ?
C13 C14 1.365(8) . ?
C13 H13 0.93 . ?
C14 C15 1.366(8) . ?
C14 F1 1.368(5) . ?
C15 C16 1.384(7) . ?
C15 H15 0.93 . ?
C16 H16 0.93 . ?
C17 N1 1.299(6) . ?
C17 C18 1.497(6) . ?
C17 S1 1.726(5) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
O1 S2 1.442(4) . ?
O2 S2 1.441(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 29360512
