#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/96/2209678.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_2209678
loop_
_publ_author_name
'Zheng-Dong Fang'
'Ming-Wu Ding'
_publ_section_title
2-Diethylamino-6-ethyl-6-methyl-3-phenylthieno[2,3-d]pyrimidin-4(3H)-one
_journal_coeditor_code           WK2013
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2862
_journal_page_last               o2863
_journal_paper_doi               10.1107/S1600536806021799
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C19 H23 N3 O S'
_chemical_formula_moiety         'C19 H23 N3 O S'
_chemical_formula_sum            'C19 H23 N3 O S'
_chemical_formula_weight         341.46
_chemical_melting_point          418
_chemical_name_systematic
;
2-Diethylamino-6-ethyl-6-methyl-3-phenylthieno[2,3-d]pyrimidin-4(3H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.269(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8085(10)
_cell_length_b                   9.5503(11)
_cell_length_c                   22.037(3)
_cell_measurement_reflns_used    3015
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      24.83
_cell_measurement_theta_min      2.33
_cell_volume                     1838.9(4)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  SHELXTL
_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 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  0.0545
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11310
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.308
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4174
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0535
_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)+(0.0682P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1365
_reflns_number_gt                3015
_reflns_number_total             4174
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wk2013.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_cell_volume        1839.0(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209678
_cod_database_fobs_code          2209678
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.2748(3) 0.2136(2) 0.47246(12) 0.0772(7) Uani d . 1
H H1A 0.1909 0.2297 0.4955 0.116 Uiso calc R 1
H H1B 0.3375 0.1390 0.4910 0.116 Uiso calc R 1
H H1C 0.2358 0.1882 0.4313 0.116 Uiso calc R 1
C C2 0.3693(2) 0.3452(2) 0.47186(9) 0.0562(5) Uani d . 1
H H2A 0.4083 0.3702 0.5136 0.067 Uiso calc R 1
H H2B 0.4563 0.3270 0.4501 0.067 Uiso calc R 1
C C3 0.2044(3) 0.5770(3) 0.54139(9) 0.0739(7) Uani d . 1
H H3A 0.2433 0.4926 0.5613 0.111 Uiso calc R 1
H H3B 0.1007 0.5915 0.5491 0.111 Uiso calc R 1
H H3C 0.2662 0.6549 0.5570 0.111 Uiso calc R 1
C C4 0.2803(2) 0.4659(2) 0.44234(8) 0.0456(4) Uani d . 1
C C5 0.2090(2) 0.5642(2) 0.47370(9) 0.0543(5) Uani d . 1
C C6 0.1628(2) 0.60491(19) 0.36148(8) 0.0432(4) Uani d . 1
C C7 0.25372(19) 0.49043(18) 0.37756(8) 0.0396(4) Uani d . 1
C C8 0.3169(2) 0.41712(18) 0.32959(8) 0.0415(4) Uani d . 1
C C9 0.16679(19) 0.58387(17) 0.25994(8) 0.0395(4) Uani d . 1
C C10 0.35126(19) 0.42110(18) 0.22131(7) 0.0396(4) Uani d . 1
C C11 0.3336(2) 0.2844(2) 0.20222(9) 0.0521(5) Uani d . 1
H H11 0.2669 0.2254 0.2196 0.062 Uiso calc R 1
C C12 0.4153(3) 0.2350(2) 0.15717(10) 0.0665(6) Uani d . 1
H H12 0.4041 0.1426 0.1442 0.080 Uiso calc R 1
C C13 0.5132(3) 0.3230(3) 0.13161(10) 0.0693(7) Uani d . 1
H H13 0.5677 0.2900 0.1011 0.083 Uiso calc R 1
C C14 0.5309(2) 0.4598(3) 0.15098(9) 0.0626(6) Uani d . 1
H H14 0.5973 0.5187 0.1334 0.075 Uiso calc R 1
C C15 0.4502(2) 0.5102(2) 0.19660(8) 0.0477(4) Uani d . 1
H H15 0.4627 0.6022 0.2102 0.057 Uiso calc R 1
C C16 0.0477(2) 0.5203(2) 0.15713(9) 0.0518(5) Uani d . 1
H H16A -0.0617 0.5372 0.1527 0.062 Uiso calc R 1
H H16B 0.0661 0.4271 0.1740 0.062 Uiso calc R 1
C C17 0.1021(3) 0.5266(2) 0.09473(9) 0.0670(6) Uani d . 1
H H17A 0.0849 0.6189 0.0780 0.101 Uiso calc R 1
H H17B 0.0464 0.4596 0.0681 0.101 Uiso calc R 1
H H17C 0.2094 0.5053 0.0985 0.101 Uiso calc R 1
C C18 0.0651(2) 0.7675(2) 0.19106(9) 0.0509(5) Uani d . 1
H H18A -0.0163 0.7812 0.2163 0.061 Uiso calc R 1
H H18B 0.0216 0.7789 0.1487 0.061 Uiso calc R 1
C C19 0.1857(3) 0.8767(2) 0.20685(10) 0.0636(6) Uani d . 1
H H19A 0.2169 0.8763 0.2502 0.095 Uiso calc R 1
H H19B 0.1451 0.9671 0.1946 0.095 Uiso calc R 1
H H19C 0.2723 0.8568 0.1859 0.095 Uiso calc R 1
N N1 0.26886(15) 0.47293(14) 0.26980(6) 0.0381(3) Uani d . 1
N N2 0.11491(17) 0.65260(15) 0.30406(7) 0.0450(4) Uani d . 1
N N3 0.12541(16) 0.62379(15) 0.20014(7) 0.0436(4) Uani d . 1
O O1 0.40594(18) 0.31988(14) 0.33535(6) 0.0634(4) Uani d . 1
S S1 0.10895(7) 0.68593(6) 0.42534(2) 0.0605(2) 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 H1A 109.5 ?
C2 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
C2 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
C4 C2 C1 112.75(18) ?
C4 C2 H2A 109.0 ?
C1 C2 H2A 109.0 ?
C4 C2 H2B 109.0 ?
C1 C2 H2B 109.0 ?
H2A C2 H2B 107.8 y
C5 C3 H3A 109.5 ?
C5 C3 H3B 109.5 ?
H3A C3 H3B 109.5 ?
C5 C3 H3C 109.5 ?
H3A C3 H3C 109.5 y
H3B C3 H3C 109.5 ?
C5 C4 C7 111.33(17) ?
C5 C4 C2 124.00(17) ?
C7 C4 C2 124.63(17) ?
C4 C5 C3 129.1(2) ?
C4 C5 S1 112.28(14) y
C3 C5 S1 118.62(16) ?
N2 C6 C7 127.41(16) y
N2 C6 S1 121.61(14) ?
C7 C6 S1 110.97(13) y
C6 C7 C4 113.70(16) ?
C6 C7 C8 117.71(15) ?
C4 C7 C8 128.47(16) ?
O1 C8 N1 119.51(16) y
O1 C8 C7 127.02(16) ?
N1 C8 C7 113.44(15) y
N2 C9 N3 119.98(16) y
N2 C9 N1 123.28(16) ?
N3 C9 N1 116.69(15) y
C11 C10 C15 121.21(16) ?
C11 C10 N1 120.08(15) y
C15 C10 N1 118.68(16) y
C10 C11 C12 119.69(19) ?
C10 C11 H11 120.2 ?
C12 C11 H11 120.2 ?
C13 C12 C11 119.8(2) ?
C13 C12 H12 120.1 ?
C11 C12 H12 120.1 ?
C12 C13 C14 120.3(2) ?
C12 C13 H13 119.8 ?
C14 C13 H13 119.8 ?
C13 C14 C15 120.3(2) ?
C13 C14 H14 119.8 ?
C15 C14 H14 119.8 ?
C10 C15 C14 118.60(19) ?
C10 C15 H15 120.7 ?
C14 C15 H15 120.7 ?
N3 C16 C17 112.47(16) y
N3 C16 H16A 109.1 y
C17 C16 H16A 109.1 ?
N3 C16 H16B 109.1 y
C17 C16 H16B 109.1 ?
H16A C16 H16B 107.8 ?
C16 C17 H17A 109.5 ?
C16 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C16 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
N3 C18 C19 112.54(16) ?
N3 C18 H18A 109.1 ?
C19 C18 H18A 109.1 ?
N3 C18 H18B 109.1 y
C19 C18 H18B 109.1 ?
H18A C18 H18B 107.8 ?
C18 C19 H19A 109.5 ?
C18 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C18 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C9 N1 C8 122.48(14) y
C9 N1 C10 121.24(14) ?
C8 N1 C10 115.62(14) ?
C9 N2 C6 115.40(15) y
C9 N3 C18 115.77(14) y
C9 N3 C16 118.33(14) ?
C18 N3 C16 113.93(14) y
C6 S1 C5 91.72(9) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.509(3) ?
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 C4 1.496(3) ?
C2 H2A 0.9700 ?
C2 H2B 0.9700 ?
C3 C5 1.502(3) ?
C3 H3A 0.9600 ?
C3 H3B 0.9600 ?
C3 H3C 0.9600 ?
C4 C5 1.365(3) ?
C4 C7 1.436(2) ?
C5 S1 1.739(2) y
C6 N2 1.361(2) y
C6 C7 1.375(2) ?
C6 S1 1.7240(18) y
C7 C8 1.437(2) ?
C8 O1 1.212(2) y
C8 N1 1.435(2) ?
C9 N2 1.303(2) y
C9 N3 1.376(2) y
C9 N1 1.389(2) ?
C10 C11 1.374(2) ?
C10 C15 1.379(2) ?
C10 N1 1.453(2) y
C11 C12 1.381(3) ?
C11 H11 0.9300 ?
C12 C13 1.374(3) ?
C12 H12 0.9300 ?
C13 C14 1.377(3) ?
C13 H13 0.9300 ?
C14 C15 1.389(3) ?
C14 H14 0.9300 ?
C15 H15 0.9300 ?
C16 N3 1.476(2) y
C16 C17 1.514(3) ?
C16 H16A 0.9700 ?
C16 H16B 0.9700 ?
C17 H17A 0.9600 ?
C17 H17B 0.9600 ?
C17 H17C 0.9600 ?
C18 N3 1.476(2) y
C18 C19 1.498(3) ?
C18 H18A 0.9700 ?
C18 H18B 0.9700 ?
C19 H19A 0.9600 ?
C19 H19B 0.9600 ?
C19 H19C 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
_geom_torsion_publ_flag
C1 C2 C4 C5 94.7(2) ?
C1 C2 C4 C7 -82.8(2) ?
C7 C4 C5 C3 178.9(2) ?
C2 C4 C5 C3 1.1(3) ?
C7 C4 C5 S1 0.3(2) ?
C2 C4 C5 S1 -177.44(15) ?
N2 C6 C7 C4 -178.44(17) y
S1 C6 C7 C4 0.5(2) y
N2 C6 C7 C8 5.3(3) y
S1 C6 C7 C8 -175.78(13) y
C5 C4 C7 C6 -0.5(2) ?
C2 C4 C7 C6 177.22(17) ?
C5 C4 C7 C8 175.24(17) ?
C2 C4 C7 C8 -7.0(3) ?
C6 C7 C8 O1 175.38(18) ?
C4 C7 C8 O1 -0.3(3) ?
C6 C7 C8 N1 -2.5(2) ?
C4 C7 C8 N1 -178.09(16) ?
C15 C10 C11 C12 -0.5(3) ?
N1 C10 C11 C12 -178.37(17) y
C10 C11 C12 C13 -0.2(3) ?
C11 C12 C13 C14 0.4(3) ?
C12 C13 C14 C15 0.1(3) ?
C11 C10 C15 C14 1.0(3) ?
N1 C10 C15 C14 178.91(16) y
C13 C14 C15 C10 -0.8(3) ?
N2 C9 N1 C8 5.0(3) ?
N3 C9 N1 C8 -177.50(14) ?
N2 C9 N1 C10 -165.23(16) ?
N3 C9 N1 C10 12.2(2) ?
O1 C8 N1 C9 179.79(16) y
C7 C8 N1 C9 -2.2(2) ?
O1 C8 N1 C10 -9.4(2) ?
C7 C8 N1 C10 168.60(14) ?
C11 C10 N1 C9 -120.08(19) ?
C15 C10 N1 C9 62.0(2) ?
C11 C10 N1 C8 69.0(2) ?
C15 C10 N1 C8 -108.95(17) ?
N3 C9 N2 C6 -179.92(15) y
N1 C9 N2 C6 -2.5(2) ?
C7 C6 N2 C9 -2.7(3) ?
S1 C6 N2 C9 178.44(13) ?
N2 C9 N3 C18 18.8(2) ?
N1 C9 N3 C18 -158.79(15) ?
N2 C9 N3 C16 -121.77(18) ?
N1 C9 N3 C16 60.7(2) ?
C19 C18 N3 C9 69.6(2) ?
C19 C18 N3 C16 -148.17(17) ?
C17 C16 N3 C9 -140.08(17) ?
C17 C16 N3 C18 78.7(2) ?
N2 C6 S1 C5 178.76(15) y
C7 C6 S1 C5 -0.25(15) ?
C4 C5 S1 C6 -0.06(16) ?
C3 C5 S1 C6 -178.80(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21127856
