#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:15:30 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178463 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/84/4028448.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_4028448
loop_
_publ_author_name
'S. Vijay Kumar'
'G. Parameshwarappa'
'H. Ila'
_publ_section_title
;
 Synthesis of 2,4,5-Trisubstituted Thiazoles via Lawesson's
 Reagent-Mediated Chemoselective Thionation-Cyclization of Functionalized
 Enamides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7362
_journal_page_last               7369
_journal_paper_doi               10.1021/jo401208u
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C22 H14 F2 N2 O S'
_chemical_formula_weight         392.41
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 94.7790(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1709(2)
_cell_length_b                   10.0287(3)
_cell_length_c                   29.5929(7)
_cell_measurement_temperature    295(2)
_cell_volume                     1825.02(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            30820
_diffrn_reflns_theta_full        29.55
_diffrn_reflns_theta_max         29.55
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_correction_T_min  0.9750
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0435
_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)+(0.0817P)²+0.1047P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1533
_reflns_number_gt                3426
_reflns_number_total             5109
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            jo401208u_si_002_2.cif
_cod_data_source_block           compound_2
_cod_database_code               4028448
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 1.2359(3) 0.12189(18) 0.30691(6) 0.0427(4) Uani 1 1 d .
C2 C 1.3644(3) 0.0084(2) 0.30695(7) 0.0541(5) Uani 1 1 d .
H2 H 1.3329 -0.0655 0.3242 0.065 Uiso 1 1 calc R
C3 C 1.5428(3) 0.0072(3) 0.28055(8) 0.0662(6) Uani 1 1 d .
H3 H 1.6309 -0.0679 0.2800 0.079 Uiso 1 1 calc R
C4 C 1.5857(3) 0.1162(3) 0.25587(8) 0.0697(7) Uani 1 1 d .
C5 C 1.4615(4) 0.2289(3) 0.25484(7) 0.0658(6) Uani 1 1 d .
H5 H 1.4946 0.3020 0.2373 0.079 Uiso 1 1 calc R
C6 C 1.2845(3) 0.2311(2) 0.28072(6) 0.0518(5) Uani 1 1 d .
H6 H 1.1970 0.3066 0.2806 0.062 Uiso 1 1 calc R
C7 C 0.7075(3) -0.09402(16) 0.43857(6) 0.0386(4) Uani 1 1 d .
C8 C 0.5302(3) -0.17998(17) 0.43581(6) 0.0444(4) Uani 1 1 d .
H8 H 0.3979 -0.1519 0.4216 0.053 Uiso 1 1 calc R
C9 C 0.5488(3) -0.30720(18) 0.45405(6) 0.0485(4) Uani 1 1 d .
H9 H 0.4311 -0.3654 0.4520 0.058 Uiso 1 1 calc R
C10 C 0.7447(3) -0.34470(17) 0.47509(6) 0.0470(4) Uani 1 1 d .
C11 C 0.9221(3) -0.26244(19) 0.47936(7) 0.0506(5) Uani 1 1 d .
H11 H 1.0522 -0.2907 0.4945 0.061 Uiso 1 1 calc R
C12 C 0.9031(3) -0.13651(17) 0.46072(6) 0.0464(4) Uani 1 1 d .
H12 H 1.0223 -0.0794 0.4630 0.056 Uiso 1 1 calc R
C13 C 0.4163(3) 0.38138(15) 0.38350(6) 0.0383(4) Uani 1 1 d .
C14 C 0.2162(3) 0.39891(17) 0.40119(6) 0.0439(4) Uani 1 1 d .
H14 H 0.1663 0.3354 0.4207 0.053 Uiso 1 1 calc R
C15 C 0.0914(3) 0.51036(18) 0.38984(7) 0.0511(5) Uani 1 1 d .
H15 H -0.0420 0.5214 0.4018 0.061 Uiso 1 1 calc R
C16 C 0.1629(3) 0.60456(19) 0.36107(7) 0.0574(5) Uani 1 1 d .
H16 H 0.0783 0.6794 0.3536 0.069 Uiso 1 1 calc R
C17 C 0.3611(3) 0.58821(19) 0.34310(7) 0.0551(5) Uani 1 1 d .
H17 H 0.4095 0.6521 0.3235 0.066 Uiso 1 1 calc R
C18 C 0.4879(3) 0.47694(17) 0.35417(6) 0.0467(4) Uani 1 1 d .
H18 H 0.6209 0.4663 0.3420 0.056 Uiso 1 1 calc R
C19 C 0.5458(3) 0.26012(15) 0.39342(6) 0.0371(4) Uani 1 1 d .
C20 C 0.7957(3) 0.10438(15) 0.38641(6) 0.0379(4) Uani 1 1 d .
C21 C 0.6827(3) 0.03992(16) 0.41786(6) 0.0393(4) Uani 1 1 d .
C22 C 0.9795(3) 0.04804(16) 0.36257(6) 0.0413(4) Uani 1 1 d .
O1 O 1.0465(2) -0.06510(13) 0.36878(6) 0.0643(4) Uani 1 1 d .
S1 S 0.47183(7) 0.14046(4) 0.431515(15) 0.04478(15) Uani 1 1 d .
F1 F 1.7612(2) 0.1129(2) 0.23091(6) 0.1073(6) Uani 1 1 d .
F2 F 0.7633(2) -0.47037(12) 0.49212(5) 0.0708(4) Uani 1 1 d .
N1 N 1.0574(2) 0.13593(14) 0.33328(5) 0.0435(3) Uani 1 1 d .
H1 H 0.9888 0.2105 0.3303 0.052 Uiso 1 1 calc R
N2 N 0.7183(2) 0.22840(13) 0.37305(5) 0.0389(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 0.0000 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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 119.83(17)
C2 C1 N1 123.70(17)
C6 C1 N1 116.45(16)
C1 C2 C3 118.8(2)
C4 C3 C2 119.5(2)
C3 C4 F1 118.2(2)
C3 C4 C5 123.1(2)
F1 C4 C5 118.6(2)
C4 C5 C6 117.9(2)
C5 C6 C1 120.87(19)
C8 C7 C12 119.03(15)
C8 C7 C21 119.03(15)
C12 C7 C21 121.94(15)
C9 C8 C7 120.57(17)
C10 C9 C8 118.19(17)
F2 C10 C9 117.94(17)
F2 C10 C11 118.90(17)
C9 C10 C11 123.16(17)
C10 C11 C12 118.34(17)
C11 C12 C7 120.68(17)
C18 C13 C14 119.09(15)
C18 C13 C19 119.93(15)
C14 C13 C19 120.89(15)
C15 C14 C13 120.29(17)
C16 C15 C14 120.46(18)
C15 C16 C17 119.88(17)
C16 C17 C18 120.29(18)
C17 C18 C13 119.99(17)
N2 C19 C13 124.01(15)
N2 C19 S1 113.61(12)
C13 C19 S1 122.28(12)
C21 C20 N2 115.89(14)
C21 C20 C22 126.22(14)
N2 C20 C22 117.63(14)
C20 C21 C7 131.97(15)
C20 C21 S1 108.70(12)
C7 C21 S1 119.27(12)
O1 C22 N1 124.76(16)
O1 C22 C20 122.87(16)
N1 C22 C20 112.36(14)
C21 S1 C19 90.45(8)
C22 N1 C1 128.76(15)
C19 N2 C20 111.33(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.387(2)
C1 C6 1.388(3)
C1 N1 1.409(2)
C2 C3 1.402(3)
C3 C4 1.353(4)
C4 F1 1.362(2)
C4 C5 1.364(4)
C5 C6 1.386(3)
C7 C8 1.390(2)
C7 C12 1.392(2)
C7 C21 1.479(2)
C8 C9 1.386(2)
C9 C10 1.366(3)
C10 F2 1.359(2)
C10 C11 1.368(3)
C11 C12 1.379(2)
C13 C18 1.390(2)
C13 C14 1.392(2)
C13 C19 1.471(2)
C14 C15 1.383(2)
C15 C16 1.369(3)
C16 C17 1.384(3)
C17 C18 1.386(2)
C19 N2 1.306(2)
C19 S1 1.7334(16)
C20 C21 1.370(2)
C20 N2 1.378(2)
C20 C22 1.496(2)
C21 S1 1.7207(17)
C22 O1 1.216(2)
C22 N1 1.352(2)
