#------------------------------------------------------------------------------
#$Date: 2025-08-22 15:50:14 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301863 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/54/7205438.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_7205438
loop_
_publ_author_name
'Peterson, Matthew L.'
'Stanton, Mary K.'
'Kelly, Ron C.'
'Staples, Richard'
'Cheng, Alan'
_publ_section_title
;
 Preparation, solid state characterization, and single crystal
 structure analysis of
 N-(4-(6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide
 crystal forms
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              1170
_journal_paper_doi               10.1039/c0ce00544d
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C20 H15 F3 N4 O3 S'
_chemical_formula_weight         448.42
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.910(4)
_cell_angle_beta                 91.332(4)
_cell_angle_gamma                98.650(4)
_cell_formula_units_Z            2
_cell_length_a                   4.8813(11)
_cell_length_b                   10.601(2)
_cell_length_c                   18.823(4)
_cell_measurement_reflns_used    809
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.81
_cell_measurement_theta_min      2.18
_cell_volume                     955.1(3)
_computing_cell_refinement       'SMART (BRUKER, V5.625, 2001)'
_computing_data_collection       'ASTRO (BRUKER, V5.007, 1997)'
_computing_data_reduction        'SAINT (BRUKER, V6.22, 2001)'
_computing_molecular_graphics    'SHELXTL (BRUKER, 2000, V6.1)'
_computing_publication_material  'XCIF (Sheldrick and BRUKER, 1997, V5.1)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       'ω, 0.3 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6875
_diffrn_reflns_theta_full        27.92
_diffrn_reflns_theta_max         27.92
_diffrn_reflns_theta_min         1.96
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         4544
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0647P)²+0.2500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1261
_reflns_number_gt                3550
_reflns_number_total             4544
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0CE00544D.TXT
_cod_data_source_block           FB_H20
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        955.1(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7205438
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
S1 S 0.18600(10) 0.42576(4) 0.16982(3) 0.02330(14) Uani 1 1 d . . .
O1 O 0.6777(3) 0.04864(13) 0.17581(8) 0.0276(3) Uani 1 1 d . . .
O2 O -0.1906(3) 0.46347(14) 0.07590(8) 0.0335(3) Uani 1 1 d . . .
F1 F -0.5415(4) -0.36745(15) 0.51692(9) 0.0622(5) Uani 1 1 d . . .
F2 F -0.2217(4) -0.2385(2) 0.57987(9) 0.0696(5) Uani 1 1 d . . .
F3 F -0.5574(3) -0.16780(16) 0.53285(9) 0.0584(5) Uani 1 1 d . . .
N1 N 0.4386(4) -0.28625(16) 0.25711(10) 0.0282(4) Uani 1 1 d . . .
N2 N 0.7024(3) -0.15933(16) 0.17888(9) 0.0261(4) Uani 1 1 d . . .
N3 N 0.2849(3) 0.19633(15) 0.11980(9) 0.0234(3) Uani 1 1 d . . .
N4 N -0.0421(4) 0.27196(17) 0.05044(10) 0.0257(4) Uani 1 1 d . . .
H1 H -0.062(5) 0.211(2) 0.0192(14) 0.035(7) Uiso 1 1 d . . .
C1 C -0.3846(5) -0.2530(2) 0.52075(13) 0.0367(5) Uani 1 1 d . . .
C2 C -0.2192(4) -0.2367(2) 0.45573(12) 0.0299(5) Uani 1 1 d . . .
C3 C -0.1664(5) -0.1176(2) 0.43143(13) 0.0359(5) Uani 1 1 d . . .
H2 H -0.248(6) -0.050(3) 0.4506(15) 0.055(8) Uiso 1 1 d . . .
C4 C 0.0072(5) -0.1007(2) 0.37551(13) 0.0337(5) Uani 1 1 d . . .
H3 H 0.044(5) -0.018(3) 0.3626(15) 0.050(8) Uiso 1 1 d . . .
C5 C 0.1289(4) -0.20117(19) 0.34226(11) 0.0253(4) Uani 1 1 d . . .
C6 C 0.0658(5) -0.3210(2) 0.36587(13) 0.0342(5) Uani 1 1 d . . .
H4 H 0.137(5) -0.386(3) 0.3436(15) 0.042(7) Uiso 1 1 d . . .
C7 C -0.1055(5) -0.3387(2) 0.42221(13) 0.0352(5) Uani 1 1 d . . .
H5 H -0.146(5) -0.418(3) 0.4362(14) 0.044(7) Uiso 1 1 d . . .
C8 C 0.3253(4) -0.18310(18) 0.28370(11) 0.0240(4) Uani 1 1 d . . .
C9 C 0.3951(4) -0.06549(19) 0.25821(12) 0.0268(4) Uani 1 1 d . . .
H6 H 0.320(4) 0.008(2) 0.2765(12) 0.028(6) Uiso 1 1 d . . .
C10 C 0.5881(4) -0.05944(18) 0.20559(11) 0.0238(4) Uani 1 1 d . . .
C11 C 0.6176(4) -0.26870(19) 0.20624(12) 0.0282(4) Uani 1 1 d . . .
H7 H 0.696(5) -0.342(2) 0.1883(13) 0.034(6) Uiso 1 1 d . . .
C12 C 0.6326(4) 0.16642(18) 0.21213(11) 0.0238(4) Uani 1 1 d . . .
C13 C 0.7818(4) 0.21603(19) 0.27479(11) 0.0273(4) Uani 1 1 d . . .
H8 H 0.904(4) 0.164(2) 0.2943(11) 0.023(5) Uiso 1 1 d . . .
C14 C 0.7496(4) 0.3369(2) 0.30916(12) 0.0284(4) Uani 1 1 d . . .
H9 H 0.853(5) 0.372(2) 0.3498(14) 0.033(6) Uiso 1 1 d . . .
C15 C 0.5721(4) 0.4091(2) 0.28070(11) 0.0260(4) Uani 1 1 d . . .
H10 H 0.547(4) 0.492(2) 0.3037(12) 0.028(6) Uiso 1 1 d . . .
C16 C 0.4244(4) 0.35765(18) 0.21724(10) 0.0218(4) Uani 1 1 d . . .
C17 C 0.4472(4) 0.23533(17) 0.18164(10) 0.0222(4) Uani 1 1 d . . .
C18 C 0.1389(4) 0.28579(18) 0.10818(11) 0.0228(4) Uani 1 1 d . . .
C19 C -0.2014(4) 0.3631(2) 0.03590(11) 0.0274(4) Uani 1 1 d . . .
C20 C -0.3788(5) 0.3294(2) -0.03097(14) 0.0347(5) Uani 1 1 d . . .
H11 H -0.505(6) 0.380(3) -0.0310(16) 0.058(9) Uiso 1 1 d . . .
H12 H -0.484(6) 0.242(3) -0.0348(15) 0.051(8) Uiso 1 1 d . . .
H13 H -0.267(7) 0.333(3) -0.072(2) 0.076(10) Uiso 1 1 d . . .
O1S O 0.0912(4) 0.91943(18) 0.06651(10) 0.0444(5) Uani 1 1 d . . .
H1S H -0.022(6) 0.901(3) 0.0978(17) 0.052(9) Uiso 1 1 d . . .
H2S H 0.146(6) 0.995(3) 0.0713(17) 0.057(9) Uiso 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
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
C16 S1 C18 88.17(9) . . ?
C10 O1 C12 117.90(15) . . ?
C11 N1 C8 116.50(17) . . ?
C10 N2 C11 115.21(17) . . ?
C18 N3 C17 109.33(16) . . ?
C18 N4 C19 124.04(18) . . ?
C18 N4 H1 124.2(18) . . ?
C19 N4 H1 111.6(18) . . ?
F1 C1 F3 105.5(2) . . ?
F1 C1 F2 107.4(2) . . ?
F3 C1 F2 105.5(2) . . ?
F1 C1 C2 112.9(2) . . ?
F3 C1 C2 113.45(19) . . ?
F2 C1 C2 111.54(19) . . ?
C7 C2 C3 119.8(2) . . ?
C7 C2 C1 119.98(19) . . ?
C3 C2 C1 120.1(2) . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H2 118.5(18) . . ?
C2 C3 H2 121.8(18) . . ?
C3 C4 C5 121.3(2) . . ?
C3 C4 H3 116.7(17) . . ?
C5 C4 H3 121.9(17) . . ?
C4 C5 C6 118.1(2) . . ?
C4 C5 C8 121.97(18) . . ?
C6 C5 C8 119.96(19) . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H4 120.8(17) . . ?
C5 C6 H4 118.2(17) . . ?
C6 C7 C2 120.1(2) . . ?
C6 C7 H5 119.3(17) . . ?
C2 C7 H5 120.6(17) . . ?
N1 C8 C9 120.92(19) . . ?
N1 C8 C5 116.86(17) . . ?
C9 C8 C5 122.21(18) . . ?
C10 C9 C8 116.86(18) . . ?
C10 C9 H6 120.8(13) . . ?
C8 C9 H6 122.3(13) . . ?
N2 C10 O1 113.15(17) . . ?
N2 C10 C9 123.21(17) . . ?
O1 C10 C9 123.63(17) . . ?
N1 C11 N2 127.29(19) . . ?
N1 C11 H7 115.5(14) . . ?
N2 C11 H7 117.2(14) . . ?
C13 C12 C17 121.04(18) . . ?
C13 C12 O1 119.82(17) . . ?
C17 C12 O1 119.04(18) . . ?
C12 C13 C14 120.15(19) . . ?
C12 C13 H8 117.9(13) . . ?
C14 C13 H8 121.9(13) . . ?
C15 C14 C13 120.9(2) . . ?
C15 C14 H9 118.5(15) . . ?
C13 C14 H9 120.5(15) . . ?
C14 C15 C16 118.06(19) . . ?
C14 C15 H10 122.0(14) . . ?
C16 C15 H10 119.9(14) . . ?
C15 C16 C17 122.76(17) . . ?
C15 C16 S1 128.09(15) . . ?
C17 C16 S1 109.14(15) . . ?
N3 C17 C12 126.73(18) . . ?
N3 C17 C16 116.22(16) . . ?
C12 C17 C16 117.05(18) . . ?
N3 C18 N4 121.76(18) . . ?
N3 C18 S1 117.14(15) . . ?
N4 C18 S1 121.10(14) . . ?
O2 C19 N4 120.8(2) . . ?
O2 C19 C20 124.26(19) . . ?
N4 C19 C20 114.96(19) . . ?
C19 C20 H11 110(2) . . ?
C19 C20 H12 112.5(16) . . ?
H11 C20 H12 105(2) . . ?
C19 C20 H13 110(2) . . ?
H11 C20 H13 112(3) . . ?
H12 C20 H13 107(3) . . ?
H1S O1S H2S 111(3) . . ?
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
S1 C16 1.7412(19) . ?
S1 C18 1.753(2) . ?
O1 C10 1.354(2) . ?
O1 C12 1.400(2) . ?
O2 C19 1.221(3) . ?
F1 C1 1.327(3) . ?
F2 C1 1.332(3) . ?
F3 C1 1.330(3) . ?
N1 C11 1.322(3) . ?
N1 C8 1.347(3) . ?
N2 C10 1.322(3) . ?
N2 C11 1.338(3) . ?
N3 C18 1.304(2) . ?
N3 C17 1.377(3) . ?
N4 C18 1.364(3) . ?
N4 C19 1.376(3) . ?
N4 H1 0.81(3) . ?
C1 C2 1.495(3) . ?
C2 C7 1.381(3) . ?
C2 C3 1.384(3) . ?
C3 C4 1.378(3) . ?
C3 H2 0.92(3) . ?
C4 C5 1.388(3) . ?
C4 H3 0.93(3) . ?
C5 C6 1.390(3) . ?
C5 C8 1.489(3) . ?
C6 C7 1.379(3) . ?
C6 H4 0.88(3) . ?
C7 H5 0.91(3) . ?
C8 C9 1.387(3) . ?
C9 C10 1.383(3) . ?
C9 H6 0.94(2) . ?
C11 H7 0.95(2) . ?
C12 C13 1.376(3) . ?
C12 C17 1.399(3) . ?
C13 C14 1.397(3) . ?
C13 H8 0.97(2) . ?
C14 C15 1.378(3) . ?
C14 H9 0.91(3) . ?
C15 C16 1.389(3) . ?
C15 H10 0.96(2) . ?
C16 C17 1.407(3) . ?
C19 C20 1.486(3) . ?
C20 H11 0.88(3) . ?
C20 H12 0.98(3) . ?
C20 H13 0.95(4) . ?
O1S H1S 0.84(3) . ?
O1S H2S 0.80(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H1 O1S 0.81(3) 1.98(3) 2.788(3) 172(2) 2_565
O1S H1S N2 0.84(3) 2.15(3) 2.985(3) 176(3) 1_465
O1S H1S O1 0.84(3) 2.65(3) 3.245(2) 130(2) 1_465
O1S H2S N3 0.80(3) 2.22(3) 2.988(2) 162(3) 1_565
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 C7 -38.0(3) . . . . ?
F3 C1 C2 C7 -158.0(2) . . . . ?
F2 C1 C2 C7 83.0(3) . . . . ?
F1 C1 C2 C3 145.7(2) . . . . ?
F3 C1 C2 C3 25.7(3) . . . . ?
F2 C1 C2 C3 -93.3(3) . . . . ?
C7 C2 C3 C4 -2.2(4) . . . . ?
C1 C2 C3 C4 174.1(2) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C3 C4 C5 C8 -177.6(2) . . . . ?
C4 C5 C6 C7 -2.1(3) . . . . ?
C8 C5 C6 C7 177.0(2) . . . . ?
C5 C6 C7 C2 0.5(4) . . . . ?
C3 C2 C7 C6 1.6(4) . . . . ?
C1 C2 C7 C6 -174.7(2) . . . . ?
C11 N1 C8 C9 0.1(3) . . . . ?
C11 N1 C8 C5 -178.54(18) . . . . ?
C4 C5 C8 N1 177.66(19) . . . . ?
C6 C5 C8 N1 -1.4(3) . . . . ?
C4 C5 C8 C9 -1.0(3) . . . . ?
C6 C5 C8 C9 -180.0(2) . . . . ?
N1 C8 C9 C10 -1.0(3) . . . . ?
C5 C8 C9 C10 177.56(18) . . . . ?
C11 N2 C10 O1 -179.31(17) . . . . ?
C11 N2 C10 C9 0.2(3) . . . . ?
C12 O1 C10 N2 -162.86(17) . . . . ?
C12 O1 C10 C9 17.6(3) . . . . ?
C8 C9 C10 N2 0.9(3) . . . . ?
C8 C9 C10 O1 -179.67(18) . . . . ?
C8 N1 C11 N2 1.1(3) . . . . ?
C10 N2 C11 N1 -1.3(3) . . . . ?
C10 O1 C12 C13 71.1(2) . . . . ?
C10 O1 C12 C17 -112.6(2) . . . . ?
C17 C12 C13 C14 0.1(3) . . . . ?
O1 C12 C13 C14 176.31(17) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 C17 0.6(3) . . . . ?
C14 C15 C16 S1 179.49(15) . . . . ?
C18 S1 C16 C15 -178.70(19) . . . . ?
C18 S1 C16 C17 0.34(14) . . . . ?
C18 N3 C17 C12 -179.96(18) . . . . ?
C18 N3 C17 C16 -0.4(2) . . . . ?
C13 C12 C17 N3 -179.47(18) . . . . ?
O1 C12 C17 N3 4.3(3) . . . . ?
C13 C12 C17 C16 1.0(3) . . . . ?
O1 C12 C17 C16 -175.25(16) . . . . ?
C15 C16 C17 N3 179.08(17) . . . . ?
S1 C16 C17 N3 0.0(2) . . . . ?
C15 C16 C17 C12 -1.4(3) . . . . ?
S1 C16 C17 C12 179.54(14) . . . . ?
C17 N3 C18 N4 -179.57(17) . . . . ?
C17 N3 C18 S1 0.7(2) . . . . ?
C19 N4 C18 N3 179.77(18) . . . . ?
C19 N4 C18 S1 -0.5(3) . . . . ?
C16 S1 C18 N3 -0.65(15) . . . . ?
C16 S1 C18 N4 179.65(17) . . . . ?
C18 N4 C19 O2 -1.0(3) . . . . ?
C18 N4 C19 C20 178.42(19) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653733
2 PubChem 139195673
