#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/29/2222964.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_2222964
loop_
_publ_author_name
'Zheng, Ai-Hua'
'Ren, Yan-Mei'
'Xu, Jing'
_publ_section_title
;Ethyl
 5-methyl-4-oxo-3-phenyl-2-propylamino-3,4-dihydrothieno[2,3-d]pyrimidine-6-carboxylate
;
_journal_coeditor_code           AT2864
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2266
_journal_paper_doi               10.1107/S1600536809033595
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H21 N3 O3 S'
_chemical_formula_moiety         'C19 H21 N3 O3 S'
_chemical_formula_sum            'C19 H21 N3 O3 S'
_chemical_formula_weight         371.45
_chemical_name_systematic
;
Ethyl 5-methyl-4-oxo-3-phenyl-2-propylamino-3,4-
dihydrothieno[2,3-d]pyrimidine-6-carboxylate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1682(2)
_cell_length_b                   14.1247(3)
_cell_length_c                   16.0672(5)
_cell_measurement_reflns_used    4659
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      2.54
_cell_volume                     1853.73(8)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10064
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.9804
_exptl_absorpt_correction_T_min  0.9689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.371
_refine_ls_abs_structure_details 'Flack (1983), 1861 Freidel pairs'
_refine_ls_abs_structure_Flack   0.08(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4472
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0527
_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)+(0.0772P)²+0.1133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1337
_refine_ls_wR_factor_ref         0.1361
_reflns_number_gt                4226
_reflns_number_total             4472
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2864.cif
_cod_data_source_block           I
_cod_database_code               2222964
_cod_database_fobs_code          2222964
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2534(2) 0.22884(14) 0.48554(12) 0.0322(4) Uani d . 1 . .
C C2 0.3341(3) 0.15050(17) 0.45355(15) 0.0412(5) Uani d . 1 . .
H H2 0.3794 0.1052 0.4887 0.049 Uiso calc R 1 . .
C C3 0.3457(3) 0.14132(19) 0.36796(15) 0.0515(6) Uani d . 1 . .
H H3 0.4008 0.0895 0.3457 0.062 Uiso calc R 1 . .
C C4 0.2783(4) 0.2063(2) 0.31554(15) 0.0545(6) Uani d . 1 . .
H H4 0.2864 0.1984 0.2582 0.065 Uiso calc R 1 . .
C C5 0.1984(3) 0.28367(18) 0.34767(15) 0.0502(6) Uani d . 1 . .
H H5 0.1530 0.3283 0.3119 0.060 Uiso calc R 1 . .
C C6 0.1848(3) 0.29565(16) 0.43303(13) 0.0388(5) Uani d . 1 . .
H H6 0.1304 0.3479 0.4547 0.047 Uiso calc R 1 . .
C C7 0.3242(3) 0.32075(14) 0.61007(13) 0.0347(4) Uani d . 1 . .
C C8 0.3275(3) 0.32060(16) 0.69897(13) 0.0358(4) Uani d . 1 . .
C C9 0.2629(3) 0.24251(15) 0.74015(12) 0.0374(4) Uani d . 1 . .
C C10 0.1679(2) 0.17242(14) 0.62462(12) 0.0342(4) Uani d . 1 . .
C C11 0.3990(3) 0.38959(15) 0.75391(13) 0.0362(4) Uani d . 1 . .
C C12 0.3869(3) 0.36077(15) 0.83528(14) 0.0407(5) Uani d . 1 . .
C C13 -0.0094(3) 0.03243(17) 0.62828(15) 0.0483(6) Uani d . 1 . .
H H13A -0.1188 0.0260 0.6055 0.058 Uiso calc R 1 . .
H H13B -0.0201 0.0488 0.6867 0.058 Uiso calc R 1 . .
C C14 0.0757(4) -0.0588(2) 0.6213(2) 0.0725(9) Uani d . 1 . .
H H14A 0.0157 -0.1056 0.6532 0.087 Uiso calc R 1 . .
H H14B 0.1834 -0.0526 0.6462 0.087 Uiso calc R 1 . .
C C15 0.0958(7) -0.0951(3) 0.5329(3) 0.1005(15) Uani d . 1 . .
H H15A -0.0083 -0.1161 0.5121 0.151 Uiso calc R 1 . .
H H15B 0.1716 -0.1471 0.5325 0.151 Uiso calc R 1 . .
H H15C 0.1368 -0.0452 0.4981 0.151 Uiso calc R 1 . .
C C16 0.4758(4) 0.47961(18) 0.72536(16) 0.0507(6) Uani d . 1 . .
H H16A 0.3920 0.5227 0.7075 0.076 Uiso calc R 1 . .
H H16B 0.5486 0.4667 0.6798 0.076 Uiso calc R 1 . .
H H16C 0.5363 0.5074 0.7704 0.076 Uiso calc R 1 . .
C C17 0.4320(3) 0.41350(18) 0.91026(15) 0.0443(5) Uani d . 1 . .
C C18 0.4227(5) 0.4121(2) 1.05795(16) 0.0689(9) Uani d . 1 . .
H H18A 0.3688 0.4733 1.0586 0.083 Uiso calc R 1 . .
H H18B 0.5391 0.4218 1.0662 0.083 Uiso calc R 1 . .
C C19 0.3562(5) 0.3512(3) 1.12406(18) 0.0761(9) Uani d . 1 . .
H H19A 0.2411 0.3419 1.1151 0.114 Uiso calc R 1 . .
H H19B 0.3731 0.3809 1.1771 0.114 Uiso calc R 1 . .
H H19C 0.4110 0.2911 1.1231 0.114 Uiso calc R 1 . .
N N1 0.2447(2) 0.24077(12) 0.57496(10) 0.0340(4) Uani d . 1 . .
N N2 0.1836(2) 0.16896(13) 0.70577(11) 0.0393(4) Uani d . 1 . .
N N3 0.0749(2) 0.10894(14) 0.58518(13) 0.0422(4) Uani d . 1 . .
H H3A 0.055(3) 0.121(2) 0.5323(18) 0.051 Uiso d . 1 . .
O O1 0.3846(2) 0.38072(11) 0.56420(9) 0.0453(4) Uani d . 1 . .
O O2 0.4921(3) 0.49108(14) 0.91163(11) 0.0578(5) Uani d . 1 . .
O O3 0.3935(3) 0.36454(14) 0.97886(11) 0.0609(5) Uani d . 1 . .
S S1 0.29211(8) 0.25028(4) 0.84614(3) 0.04848(17) 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 C1 C2 . . 120.7(2) ?
C6 C1 N1 . . 120.37(18) ?
C2 C1 N1 . . 118.93(18) ?
C3 C2 C1 . . 118.4(2) ?
C3 C2 H2 . . 120.8 ?
C1 C2 H2 . . 120.8 ?
C4 C3 C2 . . 121.5(2) ?
C4 C3 H3 . . 119.2 ?
C2 C3 H3 . . 119.2 ?
C3 C4 C5 . . 119.7(2) ?
C3 C4 H4 . . 120.1 ?
C5 C4 H4 . . 120.1 ?
C4 C5 C6 . . 120.5(2) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C1 C6 C5 . . 119.2(2) ?
C1 C6 H6 . . 120.4 ?
C5 C6 H6 . . 120.4 ?
O1 C7 N1 . . 119.66(19) ?
O1 C7 C8 . . 126.5(2) ?
N1 C7 C8 . . 113.87(18) ?
C9 C8 C7 . . 118.0(2) ?
C9 C8 C11 . . 113.54(18) ?
C7 C8 C11 . . 128.3(2) ?
N2 C9 C8 . . 126.94(19) ?
N2 C9 S1 . . 121.50(16) ?
C8 C9 S1 . . 111.54(16) ?
N2 C10 N3 . . 120.16(19) ?
N2 C10 N1 . . 123.25(18) ?
N3 C10 N1 . . 116.58(18) ?
C12 C11 C8 . . 110.74(19) ?
C12 C11 C16 . . 125.2(2) ?
C8 C11 C16 . . 124.04(19) ?
C11 C12 C17 . . 127.9(2) ?
C11 C12 S1 . . 113.03(16) ?
C17 C12 S1 . . 118.88(17) ?
N3 C13 C14 . . 113.0(2) ?
N3 C13 H13A . . 109.0 ?
C14 C13 H13A . . 109.0 ?
N3 C13 H13B . . 109.0 ?
C14 C13 H13B . . 109.0 ?
H13A C13 H13B . . 107.8 ?
C13 C14 C15 . . 114.8(3) ?
C13 C14 H14A . . 108.6 ?
C15 C14 H14A . . 108.6 ?
C13 C14 H14B . . 108.6 ?
C15 C14 H14B . . 108.6 ?
H14A C14 H14B . . 107.6 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C11 C16 H16A . . 109.5 ?
C11 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C11 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O2 C17 O3 . . 123.5(2) ?
O2 C17 C12 . . 125.6(2) ?
O3 C17 C12 . . 110.8(2) ?
O3 C18 C19 . . 107.5(3) ?
O3 C18 H18A . . 110.2 ?
C19 C18 H18A . . 110.2 ?
O3 C18 H18B . . 110.2 ?
C19 C18 H18B . . 110.2 ?
H18A C18 H18B . . 108.5 ?
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 ?
C10 N1 C7 . . 121.80(16) ?
C10 N1 C1 . . 120.45(16) ?
C7 N1 C1 . . 117.67(16) ?
C10 N2 C9 . . 115.30(18) ?
C10 N3 C13 . . 122.80(19) ?
C10 N3 H3A . . 115.4(19) ?
C13 N3 H3A . . 121.2(19) ?
C17 O3 C18 . . 116.2(2) ?
C9 S1 C12 . . 91.12(11) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 . 1.384(3) ?
C1 C2 . 1.387(3) ?
C1 N1 . 1.448(2) ?
C2 C3 . 1.385(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.362(4) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.373(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.386(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O1 . 1.226(3) ?
C7 N1 . 1.420(3) ?
C7 C8 . 1.429(3) ?
C8 C9 . 1.390(3) ?
C8 C11 . 1.439(3) ?
C9 N2 . 1.343(3) ?
C9 S1 . 1.723(2) ?
C10 N2 . 1.311(3) ?
C10 N3 . 1.335(3) ?
C10 N1 . 1.401(3) ?
C11 C12 . 1.373(3) ?
C11 C16 . 1.490(3) ?
C12 C17 . 1.463(3) ?
C12 S1 . 1.751(2) ?
C13 N3 . 1.456(3) ?
C13 C14 . 1.468(4) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.519(5) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 O2 . 1.201(3) ?
C17 O3 . 1.339(3) ?
C18 O3 . 1.457(3) ?
C18 C19 . 1.471(5) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
N3 H3A . 0.88(3) ?
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
C6 H6 O2 2_564 0.93 2.58 3.359(3) 141.7
C2 H2 O2 3_646 0.93 2.50 3.432(3) 176.7
N3 H3A O1 4_456 0.88(3) 2.08(3) 2.863(3) 147(3)
C16 H16C O2 . 0.96 2.31 3.000(3) 128.3
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.6(3) ?
N1 C1 C2 C3 . . . . -178.1(2) ?
C1 C2 C3 C4 . . . . -0.9(4) ?
C2 C3 C4 C5 . . . . 0.8(4) ?
C3 C4 C5 C6 . . . . -0.5(4) ?
C2 C1 C6 C5 . . . . -0.3(3) ?
N1 C1 C6 C5 . . . . 178.4(2) ?
C4 C5 C6 C1 . . . . 0.2(4) ?
O1 C7 C8 C9 . . . . -175.2(2) ?
N1 C7 C8 C9 . . . . 3.3(3) ?
O1 C7 C8 C11 . . . . 0.8(4) ?
N1 C7 C8 C11 . . . . 179.28(19) ?
C7 C8 C9 N2 . . . . -6.1(3) ?
C11 C8 C9 N2 . . . . 177.4(2) ?
C7 C8 C9 S1 . . . . 175.14(16) ?
C11 C8 C9 S1 . . . . -1.4(2) ?
C9 C8 C11 C12 . . . . 0.4(3) ?
C7 C8 C11 C12 . . . . -175.7(2) ?
C9 C8 C11 C16 . . . . -179.8(2) ?
C7 C8 C11 C16 . . . . 4.1(4) ?
C8 C11 C12 C17 . . . . -174.6(2) ?
C16 C11 C12 C17 . . . . 5.6(4) ?
C8 C11 C12 S1 . . . . 0.8(2) ?
C16 C11 C12 S1 . . . . -179.1(2) ?
N3 C13 C14 C15 . . . . -60.7(4) ?
C11 C12 C17 O2 . . . . -2.1(4) ?
S1 C12 C17 O2 . . . . -177.2(2) ?
C11 C12 C17 O3 . . . . 176.3(2) ?
S1 C12 C17 O3 . . . . 1.2(3) ?
N2 C10 N1 C7 . . . . -10.4(3) ?
N3 C10 N1 C7 . . . . 169.45(18) ?
N2 C10 N1 C1 . . . . 166.03(19) ?
N3 C10 N1 C1 . . . . -14.1(3) ?
O1 C7 N1 C10 . . . . -177.29(19) ?
C8 C7 N1 C10 . . . . 4.1(3) ?
O1 C7 N1 C1 . . . . 6.2(3) ?
C8 C7 N1 C1 . . . . -172.42(17) ?
C6 C1 N1 C10 . . . . 120.7(2) ?
C2 C1 N1 C10 . . . . -60.5(3) ?
C6 C1 N1 C7 . . . . -62.7(3) ?
C2 C1 N1 C7 . . . . 116.0(2) ?
N3 C10 N2 C9 . . . . -172.1(2) ?
N1 C10 N2 C9 . . . . 7.7(3) ?
C8 C9 N2 C10 . . . . 0.5(3) ?
S1 C9 N2 C10 . . . . 179.13(17) ?
N2 C10 N3 C13 . . . . -1.6(3) ?
N1 C10 N3 C13 . . . . 178.5(2) ?
C14 C13 N3 C10 . . . . -100.7(3) ?
O2 C17 O3 C18 . . . . 2.3(4) ?
C12 C17 O3 C18 . . . . -176.2(3) ?
C19 C18 O3 C17 . . . . 173.9(3) ?
N2 C9 S1 C12 . . . . -177.32(19) ?
C8 C9 S1 C12 . . . . 1.53(17) ?
C11 C12 S1 C9 . . . . -1.33(19) ?
C17 C12 S1 C9 . . . . 174.47(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743166
