#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/14/2211472.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2211472
loop_
_publ_author_name
'Sheng-Zhen Xu'
'Yang-Gen Hu'
_publ_section_title
2-(tert-Butylamino)-3-phenylbenzo[4,5]thieno[3,2-d]pyrimidin-4(3H)-one
_journal_coeditor_code           IS2099
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5647
_journal_page_last               o5648
_journal_paper_doi               10.1107/S1600536806048100
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C20 H19 N3 O S'
_chemical_formula_moiety         'C20 H19 N3 O S'
_chemical_formula_sum            'C20 H19 N3 O S'
_chemical_formula_weight         349.44
_chemical_name_systematic
;
2-(tert-Butylamino)-3-phenyl-3H-benzo[4,5]thieno[3,2-e]pyrimidin-4-one
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                104.928(3)
_cell_angle_beta                 115.988(2)
_cell_angle_gamma                91.557(3)
_cell_formula_units_Z            2
_cell_length_a                   9.7106(15)
_cell_length_b                   10.1139(15)
_cell_length_c                   10.5568(16)
_cell_measurement_reflns_used    1055
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.25
_cell_volume                     888.7(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL (Bruker, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4495
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.25
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_correction_T_min  0.9621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0723P)²+0.077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1493
_reflns_number_gt                2179
_reflns_number_total             3058
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2099.cif
_cod_data_source_block           I
_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 1527 2010-12-29 10:47:43Z saulius 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2211472
_cod_database_fobs_code          2211472
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.7806(3) 0.1215(3) 1.1700(3) 0.0436(7) Uani d . 1
C C2 0.8745(4) 0.0945(3) 1.3019(3) 0.0519(8) Uani d . 1
H H2 0.9696 0.0659 1.3191 0.062 Uiso calc R 1
C C3 0.8220(4) 0.1114(3) 1.4056(3) 0.0571(9) Uani d . 1
H H3 0.8837 0.0939 1.4942 0.068 Uiso calc R 1
C C4 0.6811(4) 0.1533(3) 1.3835(3) 0.0561(8) Uani d . 1
H H4 0.6490 0.1624 1.4559 0.067 Uiso calc R 1
C C5 0.5883(4) 0.1817(3) 1.2541(3) 0.0506(8) Uani d . 1
H H5 0.4941 0.2115 1.2392 0.061 Uiso calc R 1
C C6 0.6376(3) 0.1651(3) 1.1454(3) 0.0390(7) Uani d . 1
C C7 0.5593(3) 0.1870(3) 1.0031(3) 0.0374(6) Uani d . 1
C C8 0.6435(3) 0.1597(3) 0.9263(3) 0.0394(7) Uani d . 1
C C9 0.5906(3) 0.1828(3) 0.7852(3) 0.0421(7) Uani d . 1
C C10 0.3683(3) 0.2556(3) 0.8253(3) 0.0392(7) Uani d . 1
C C11 0.3844(3) 0.2634(3) 0.6002(3) 0.0429(7) Uani d . 1
C C12 0.3274(3) 0.1578(3) 0.4709(3) 0.0482(7) Uani d . 1
H H12 0.3313 0.0663 0.4720 0.058 Uiso calc R 1
C C13 0.2638(4) 0.1887(4) 0.3384(3) 0.0629(10) Uani d . 1
H H13 0.2243 0.1175 0.2498 0.075 Uiso calc R 1
C C14 0.2586(4) 0.3230(5) 0.3369(4) 0.0685(11) Uani d . 1
H H14 0.2145 0.3426 0.2472 0.082 Uiso calc R 1
C C15 0.3184(4) 0.4301(4) 0.4677(4) 0.0668(10) Uani d . 1
H H15 0.3148 0.5216 0.4665 0.080 Uiso calc R 1
C C16 0.3835(4) 0.3999(3) 0.6001(3) 0.0544(8) Uani d . 1
H H16 0.4266 0.4711 0.6889 0.065 Uiso calc R 1
C C17 0.1484(3) 0.3658(3) 0.8517(3) 0.0474(8) Uani d . 1
C C18 0.2579(4) 0.4756(3) 0.9946(4) 0.0670(10) Uani d . 1
H H18A 0.3297 0.4321 1.0613 0.101 Uiso calc R 1
H H18B 0.1991 0.5247 1.0389 0.101 Uiso calc R 1
H H18C 0.3142 0.5395 0.9739 0.101 Uiso calc R 1
C C19 0.0709(4) 0.2560(4) 0.8828(4) 0.0650(9) Uani d . 1
H H19A -0.0083 0.1948 0.7915 0.098 Uiso calc R 1
H H19B 0.0250 0.2992 0.9439 0.098 Uiso calc R 1
H H19C 0.1467 0.2040 0.9331 0.098 Uiso calc R 1
C C20 0.0263(4) 0.4328(4) 0.7505(4) 0.0788(12) Uani d . 1
H H20A 0.0763 0.5094 0.7398 0.118 Uiso calc R 1
H H20B -0.0410 0.4655 0.7925 0.118 Uiso calc R 1
H H20C -0.0337 0.3658 0.6554 0.118 Uiso calc R 1
N N1 0.4199(3) 0.2336(2) 0.9536(2) 0.0435(6) Uani d . 1
N N2 0.4472(3) 0.2328(2) 0.7398(2) 0.0387(6) Uani d . 1
N N3 0.2324(3) 0.3025(3) 0.7688(2) 0.0483(6) Uani d . 1
H H3A 0.1904 0.2952 0.6762 0.058 Uiso calc R 1
O O1 0.6564(2) 0.1649(2) 0.7083(2) 0.0569(6) Uani d . 1
S S1 0.81909(9) 0.10819(9) 1.02092(8) 0.0511(3) Uani d . 1
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'
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_publ_flag
C2 C1 C6 120.6(3) ?
C2 C1 S1 127.2(2) ?
C6 C1 S1 112.20(19) ?
C3 C2 C1 117.9(3) ?
C3 C2 H2 121.1 ?
C1 C2 H2 121.1 ?
C2 C3 C4 122.6(3) ?
C2 C3 H3 118.7 ?
C4 C3 H3 118.7 ?
C5 C4 C3 119.9(3) ?
C5 C4 H4 120.0 ?
C3 C4 H4 120.0 ?
C4 C5 C6 119.1(3) ?
C4 C5 H5 120.4 ?
C6 C5 H5 120.4 ?
C5 C6 C1 119.8(2) ?
C5 C6 C7 128.4(3) ?
C1 C6 C7 111.7(2) ?
N1 C7 C8 124.7(2) ?
N1 C7 C6 123.5(2) ?
C8 C7 C6 111.8(2) ?
C7 C8 C9 120.8(3) ?
C7 C8 S1 113.9(2) ?
C9 C8 S1 125.1(2) ?
O1 C9 N2 120.9(2) ?
O1 C9 C8 126.8(3) ?
N2 C9 C8 112.3(2) ?
N1 C10 N3 119.9(2) no
N1 C10 N2 123.4(2) ?
N3 C10 N2 116.7(2) ?
C12 C11 C16 120.9(3) ?
C12 C11 N2 119.9(3) ?
C16 C11 N2 119.2(3) ?
C11 C12 C13 119.1(3) ?
C11 C12 H12 120.4 ?
C13 C12 H12 120.4 ?
C14 C13 C12 120.5(3) ?
C14 C13 H13 119.8 ?
C12 C13 H13 119.8 ?
C13 C14 C15 120.4(3) ?
C13 C14 H14 119.8 ?
C15 C14 H14 119.8 ?
C16 C15 C14 119.3(3) ?
C16 C15 H15 120.3 ?
C14 C15 H15 120.3 ?
C15 C16 C11 119.7(3) ?
C15 C16 H16 120.2 ?
C11 C16 H16 120.2 ?
N3 C17 C19 110.5(3) ?
N3 C17 C18 110.8(3) ?
C19 C17 C18 110.5(3) ?
N3 C17 C20 105.4(2) ?
C19 C17 C20 109.8(3) ?
C18 C17 C20 109.7(3) ?
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 C19 H19A 109.5 ?
C17 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C17 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C17 C20 H20A 109.5 ?
C17 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
C17 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
C10 N1 C7 116.0(2) ?
C10 N2 C9 122.7(2) ?
C10 N2 C11 120.2(2) ?
C9 N2 C11 117.1(2) ?
C10 N3 C17 126.0(2) yes
C10 N3 H3A 117.0 ?
C17 N3 H3A 117.0 ?
C8 S1 C1 90.32(13) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.393(4) ?
C1 C6 1.402(4) ?
C1 S1 1.745(3) yes
C2 C3 1.372(4) ?
C2 H2 0.9300 ?
C3 C4 1.382(4) ?
C3 H3 0.9300 ?
C4 C5 1.377(4) ?
C4 H4 0.9300 ?
C5 C6 1.400(4) ?
C5 H5 0.9300 ?
C6 C7 1.437(3) ?
C7 N1 1.367(3) ?
C7 C8 1.371(4) ?
C8 C9 1.433(4) ?
C8 S1 1.732(3) yes
C9 O1 1.219(3) ?
C9 N2 1.415(3) yes
C10 N1 1.304(3) yes
C10 N3 1.346(3) yes
C10 N2 1.400(3) yes
C11 C12 1.366(4) ?
C11 C16 1.381(4) ?
C11 N2 1.448(3) ?
C12 C13 1.384(4) ?
C12 H12 0.9300 ?
C13 C14 1.364(5) ?
C13 H13 0.9300 ?
C14 C15 1.382(5) ?
C14 H14 0.9300 ?
C15 C16 1.380(4) ?
C15 H15 0.9300 ?
C16 H16 0.9300 ?
C17 N3 1.485(3) ?
C17 C19 1.506(4) ?
C17 C18 1.519(4) ?
C17 C20 1.521(4) ?
C18 H18A 0.9600 ?
C18 H18B 0.9600 ?
C18 H18C 0.9600 ?
C19 H19A 0.9600 ?
C19 H19B 0.9600 ?
C19 H19C 0.9600 ?
C20 H20A 0.9600 ?
C20 H20B 0.9600 ?
C20 H20C 0.9600 ?
N3 H3A 0.8600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C19 H19C N1 . 0.96 2.57 3.163(4) 120
C18 H18A N1 . 0.96 2.43 2.986(4) 117
C18 H18A Cg 2_667 0.96 2.71 3.454(4) 135
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_publ_flag
C6 C1 C2 C3 0.3(5) ?
S1 C1 C2 C3 -179.9(2) ?
C1 C2 C3 C4 0.2(5) ?
C2 C3 C4 C5 -0.9(5) ?
C3 C4 C5 C6 1.1(5) ?
C4 C5 C6 C1 -0.7(4) ?
C4 C5 C6 C7 179.2(3) ?
C2 C1 C6 C5 0.0(4) ?
S1 C1 C6 C5 -179.9(2) ?
C2 C1 C6 C7 -179.9(3) ?
S1 C1 C6 C7 0.3(3) ?
C5 C6 C7 N1 2.1(5) ?
C1 C6 C7 N1 -178.0(3) ?
C5 C6 C7 C8 -179.8(3) ?
C1 C6 C7 C8 0.1(3) ?
N1 C7 C8 C9 1.7(4) ?
C6 C7 C8 C9 -176.3(2) ?
N1 C7 C8 S1 177.7(2) ?
C6 C7 C8 S1 -0.4(3) ?
C7 C8 C9 O1 178.6(3) ?
S1 C8 C9 O1 3.1(5) ?
C7 C8 C9 N2 -0.7(4) ?
S1 C8 C9 N2 -176.21(19) no
C16 C11 C12 C13 -2.0(4) ?
N2 C11 C12 C13 178.2(3) ?
C11 C12 C13 C14 0.2(5) ?
C12 C13 C14 C15 0.8(5) ?
C13 C14 C15 C16 0.0(5) ?
C14 C15 C16 C11 -1.7(5) ?
C12 C11 C16 C15 2.7(5) ?
N2 C11 C16 C15 -177.4(3) ?
N3 C10 N1 C7 -179.5(2) ?
N2 C10 N1 C7 0.5(4) ?
C8 C7 N1 C10 -1.6(4) ?
C6 C7 N1 C10 176.3(3) ?
N1 C10 N2 C9 0.4(4) ?
N3 C10 N2 C9 -179.6(2) ?
N1 C10 N2 C11 -178.2(3) ?
N3 C10 N2 C11 1.8(4) ?
O1 C9 N2 C10 -179.6(3) ?
C8 C9 N2 C10 -0.3(4) ?
O1 C9 N2 C11 -1.0(4) no
C8 C9 N2 C11 178.4(2) ?
C12 C11 N2 C10 -110.5(3) ?
C16 C11 N2 C10 69.6(4) ?
C12 C11 N2 C9 70.8(3) ?
C16 C11 N2 C9 -109.1(3) ?
N1 C10 N3 C17 15.9(4) ?
N2 C10 N3 C17 -164.2(3) ?
C19 C17 N3 C10 -75.1(4) ?
C18 C17 N3 C10 47.7(4) ?
C20 C17 N3 C10 166.3(3) ?
C7 C8 S1 C1 0.4(2) ?
C9 C8 S1 C1 176.2(3) no
C2 C1 S1 C8 179.8(3) ?
C6 C1 S1 C8 -0.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21125896
