#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/92/2209222.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_2209222
loop_
_publ_author_name
'Sheng-Zhen Xu'
'Yang-Gen Hu'
'Xiang Wang'
'Ming-Wu Ding'
_publ_section_title
;
 2-Ethoxy-3-phenyl-1-benzothieno[3,2-d]pyrimidin-4(3H)-one
;
_journal_coeditor_code           IS2030
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2229
_journal_page_last               o2230
_journal_paper_doi               10.1107/S1600536806015959
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H14 N2 O2 S'
_chemical_formula_moiety         'C18 H14 N2 O2 S'
_chemical_formula_sum            'C18 H14 N2 O2 S'
_chemical_formula_weight         322.37
_chemical_melting_point          463
_chemical_name_systematic
;
2-Ethoxy-3-phenyl-1-benzothieno[3,2-d]pyrimidin-4(3H)-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 126.2980(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   22.4877(18)
_cell_length_b                   11.2298(9)
_cell_length_c                   14.8969(12)
_cell_measurement_reflns_used    7441
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.25
_cell_volume                     3031.9(4)
_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 (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART 4K 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  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16980
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.13
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.9564
_exptl_absorpt_correction_T_min  0.9356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.345
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0451
_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)+(0.0671P)²+0.7743P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1204
_reflns_number_gt                3090
_reflns_number_total             3620
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2030.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2209222
_cod_database_fobs_code          2209222
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 -0.02951(7) -0.00160(12) 0.08998(11) 0.0408(3) Uani d . 1
C C2 -0.07988(8) 0.09192(15) 0.04456(12) 0.0494(3) Uani d . 1
H H2 -0.0645 0.1693 0.0704 0.059 Uiso calc R 1
C C3 -0.15289(9) 0.06803(18) -0.03936(14) 0.0594(4) Uani d . 1
H H3 -0.1870 0.1299 -0.0713 0.071 Uiso calc R 1
C C4 -0.17585(8) -0.04851(18) -0.07664(13) 0.0596(4) Uani d . 1
H H4 -0.2254 -0.0631 -0.1327 0.071 Uiso calc R 1
C C5 -0.12722(9) -0.14225(16) -0.03289(13) 0.0546(4) Uani d . 1
H H5 -0.1433 -0.2195 -0.0583 0.066 Uiso calc R 1
C C6 -0.05263(8) -0.11815(13) 0.05129(11) 0.0454(3) Uani d . 1
C C7 0.04878(7) 0.00306(12) 0.17617(10) 0.0380(3) Uani d . 1
C C8 0.08178(8) -0.10584(12) 0.19779(11) 0.0423(3) Uani d . 1
C C9 0.15982(8) -0.12020(12) 0.27669(11) 0.0439(3) Uani d . 1
C C10 0.15544(7) 0.09391(11) 0.30399(10) 0.0373(3) Uani d . 1
C C11 0.27430(7) -0.01167(12) 0.41539(11) 0.0403(3) Uani d . 1
C C12 0.31985(8) 0.05726(13) 0.40266(12) 0.0481(3) Uani d . 1
H H12 0.3001 0.1036 0.3392 0.058 Uiso calc R 1
C C13 0.39512(9) 0.05632(16) 0.48557(15) 0.0597(4) Uani d . 1
H H13 0.4261 0.1032 0.4783 0.072 Uiso calc R 1
C C14 0.42440(9) -0.01378(16) 0.57889(15) 0.0638(5) Uani d . 1
H H14 0.4751 -0.0145 0.6340 0.077 Uiso calc R 1
C C15 0.37891(9) -0.08225(14) 0.59035(13) 0.0592(4) Uani d . 1
H H15 0.3989 -0.1293 0.6535 0.071 Uiso calc R 1
C C16 0.30339(8) -0.08216(12) 0.50884(12) 0.0469(3) Uani d . 1
H H16 0.2726 -0.1289 0.5168 0.056 Uiso calc R 1
C C17 0.15953(8) 0.29895(11) 0.34532(12) 0.0449(3) Uani d . 1
H H17A 0.1901 0.3505 0.4094 0.054 Uiso calc R 1
H H17B 0.1137 0.2850 0.3364 0.054 Uiso calc R 1
C C18 0.14303(10) 0.36009(14) 0.24347(14) 0.0582(4) Uani d . 1
H H18A 0.1859 0.3577 0.2440 0.087 Uiso calc R 1
H H18B 0.1298 0.4415 0.2430 0.087 Uiso calc R 1
H H18C 0.1029 0.3203 0.1782 0.087 Uiso calc R 1
N N1 0.08543(6) 0.10562(10) 0.22964(9) 0.0393(3) Uani d . 1
N N2 0.19518(6) -0.01064(9) 0.33058(9) 0.0394(3) Uani d . 1
O O1 0.19509(6) -0.21130(9) 0.29867(10) 0.0609(3) Uani d . 1
O O2 0.19736(5) 0.18566(8) 0.36566(8) 0.0446(2) Uani d . 1
S S1 0.02024(2) -0.21962(3) 0.11776(3) 0.05381(15) 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
C2 C1 C6 120.55(13)
C2 C1 C7 128.29(13)
C6 C1 C7 111.15(12)
C3 C2 C1 118.93(15)
C3 C2 H2 120.5
C1 C2 H2 120.5
C2 C3 C4 120.31(16)
C2 C3 H3 119.8
C4 C3 H3 119.8
C5 C4 C3 121.81(14)
C5 C4 H4 119.1
C3 C4 H4 119.1
C4 C5 C6 118.11(15)
C4 C5 H5 120.9
C6 C5 H5 120.9
C1 C6 C5 120.28(14)
C1 C6 S1 112.45(10)
C5 C6 S1 127.27(13)
N1 C7 C8 124.16(12)
N1 C7 C1 123.24(11)
C8 C7 C1 112.60(11)
C7 C8 C9 121.72(12)
C7 C8 S1 113.31(10)
C9 C8 S1 124.94(10)
O1 C9 N2 121.14(12)
O1 C9 C8 127.18(13)
N2 C9 C8 111.67(11)
N1 C10 O2 121.38(11)
N1 C10 N2 125.90(11)
O2 C10 N2 112.70(11)
C12 C11 C16 120.70(13)
C12 C11 N2 120.16(12)
C16 C11 N2 119.14(13)
C11 C12 C13 119.14(15)
C11 C12 H12 120.4
C13 C12 H12 120.4
C14 C13 C12 120.38(16)
C14 C13 H13 119.8
C12 C13 H13 119.8
C15 C14 C13 120.02(15)
C15 C14 H14 120.0
C13 C14 H14 120.0
C14 C15 C16 120.63(15)
C14 C15 H15 119.7
C16 C15 H15 119.7
C11 C16 C15 119.12(15)
C11 C16 H16 120.4
C15 C16 H16 120.4
O2 C17 C18 111.98(13)
O2 C17 H17A 109.2
C18 C17 H17A 109.2
O2 C17 H17B 109.2
C18 C17 H17B 109.2
H17A C17 H17B 107.9
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
C10 N1 C7 115.11(11)
C10 N2 C9 121.35(11)
C10 N2 C11 120.52(10)
C9 N2 C11 118.13(10)
C10 O2 C17 116.38(10)
C8 S1 C6 90.46(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.392(2)
C1 C6 1.400(2)
C1 C7 1.4403(18)
C2 C3 1.379(2)
C2 H2 0.9300
C3 C4 1.396(3)
C3 H3 0.9300
C4 C5 1.373(2)
C4 H4 0.9300
C5 C6 1.4033(19)
C5 H5 0.9300
C6 S1 1.7444(16)
C7 N1 1.3650(16)
C7 C8 1.3664(19)
C8 C9 1.4301(19)
C8 S1 1.7366(13)
C9 O1 1.2147(17)
C9 N2 1.4265(17)
C10 N1 1.2876(16)
C10 O2 1.3300(15)
C10 N2 1.3838(16)
C11 C12 1.384(2)
C11 C16 1.384(2)
C11 N2 1.4493(17)
C12 C13 1.384(2)
C12 H12 0.9300
C13 C14 1.379(3)
C13 H13 0.9300
C14 C15 1.369(3)
C14 H14 0.9300
C15 C16 1.385(2)
C15 H15 0.9300
C16 H16 0.9300
C17 O2 1.4591(15)
C17 C18 1.498(2)
C17 H17A 0.9700
C17 H17B 0.9700
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
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
C6 C1 C2 C3 -0.2(2)
C7 C1 C2 C3 178.95(14)
C1 C2 C3 C4 1.0(2)
C2 C3 C4 C5 -0.8(2)
C3 C4 C5 C6 -0.2(2)
C2 C1 C6 C5 -0.9(2)
C7 C1 C6 C5 179.87(12)
C2 C1 C6 S1 178.44(11)
C7 C1 C6 S1 -0.82(15)
C4 C5 C6 C1 1.0(2)
C4 C5 C6 S1 -178.16(12)
C2 C1 C7 N1 2.0(2)
C6 C1 C7 N1 -178.85(12)
C2 C1 C7 C8 -177.88(14)
C6 C1 C7 C8 1.30(17)
N1 C7 C8 C9 -2.9(2)
C1 C7 C8 C9 176.94(12)
N1 C7 C8 S1 178.93(10)
C1 C7 C8 S1 -1.22(16)
C7 C8 C9 O1 -176.52(15)
S1 C8 C9 O1 1.4(2)
C7 C8 C9 N2 3.1(2)
S1 C8 C9 N2 -178.98(10)
C16 C11 C12 C13 -0.9(2)
N2 C11 C12 C13 178.97(13)
C11 C12 C13 C14 0.9(2)
C12 C13 C14 C15 -0.5(3)
C13 C14 C15 C16 0.1(2)
C12 C11 C16 C15 0.5(2)
N2 C11 C16 C15 -179.39(12)
C14 C15 C16 C11 -0.1(2)
O2 C10 N1 C7 -177.12(12)
N2 C10 N1 C7 1.9(2)
C8 C7 N1 C10 0.30(19)
C1 C7 N1 C10 -179.54(12)
N1 C10 N2 C9 -1.4(2)
O2 C10 N2 C9 177.65(11)
N1 C10 N2 C11 179.24(13)
O2 C10 N2 C11 -1.71(17)
O1 C9 N2 C10 178.51(14)
C8 C9 N2 C10 -1.13(18)
O1 C9 N2 C11 -2.1(2)
C8 C9 N2 C11 178.24(12)
C12 C11 N2 C10 -60.74(17)
C16 C11 N2 C10 119.17(14)
C12 C11 N2 C9 119.88(14)
C16 C11 N2 C9 -60.21(17)
N1 C10 O2 C17 0.79(18)
N2 C10 O2 C17 -178.31(11)
C18 C17 O2 C10 -78.89(16)
C7 C8 S1 C6 0.63(12)
C9 C8 S1 C6 -177.45(13)
C1 C6 S1 C8 0.13(11)
C5 C6 S1 C8 179.39(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21128154
2 PubChem 139069666
