#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/79/2227911.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_2227911
loop_
_publ_author_name
'Meng, Shuang-Ming'
'Xie, Hai'
'Fan, Yue-Qin'
'Jing, Bu-qin'
'Guo, Yong'
_publ_section_title
;
 3-Phenyl-2-(pyrrolidin-1-yl)-5,6-dihydro-8H-thiopyrano[4',3':4,5]thieno[2,3-d]pyrimidin-4(3H)-one
;
_journal_coeditor_code           PV2315
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2403
_journal_paper_doi               10.1107/S1600536810032794
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H19 N3 O S2'
_chemical_formula_moiety         'C19 H19 N3 O S2'
_chemical_formula_sum            'C19 H19 N3 O S2'
_chemical_formula_weight         369.49
_chemical_name_systematic
;
3-Phenyl-2-(pyrrolidin-1-yl)-5,6-dihydro-8H-
thiopyrano[4',3':4,5]thieno[2,3-d]pyrimidin-4(3H)-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           SHELXL-97
_cell_angle_alpha                73.6680(10)
_cell_angle_beta                 88.6290(10)
_cell_angle_gamma                79.5680(10)
_cell_formula_units_Z            2
_cell_length_a                   8.1484(8)
_cell_length_b                   9.3455(9)
_cell_length_c                   12.1834(12)
_cell_measurement_reflns_used    2113
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      0.806
_cell_measurement_theta_min      0.877
_cell_volume                     875.26(15)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω scans'
_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  0.0158
_diffrn_reflns_av_sigmaI/netI    0.0294
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4828
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.74
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  0.9452
_exptl_absorpt_correction_T_min  0.9110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.444
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3349
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0433
_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)+(0.0534P)²+0.3774P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1192
_reflns_number_gt                2709
_reflns_number_total             3349
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2315.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               2227911
_cod_database_fobs_code          2227911
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.47598(8) 0.15501(7) 0.76959(5) 0.04843(19) Uani d . 1 . .
S S2 0.06845(11) -0.09908(9) 0.87874(6) 0.0725(3) Uani d . 1 . .
N N1 0.5900(2) 0.2755(2) 0.55975(14) 0.0395(4) Uani d . 1 . .
N N3 0.4362(2) 0.27799(19) 0.39525(13) 0.0364(4) Uani d . 1 . .
N N2 0.6791(2) 0.3883(2) 0.38313(14) 0.0370(4) Uani d . 1 . .
O O1 0.2152(2) 0.1535(2) 0.40870(14) 0.0604(5) Uani d . 1 . .
C C7 0.3484(3) 0.1486(2) 0.58029(17) 0.0374(5) Uani d . 1 . .
C C5 0.4765(3) 0.1994(2) 0.62133(17) 0.0383(5) Uani d . 1 . .
C C13 0.8080(3) 0.4343(3) 0.44164(18) 0.0409(5) Uani d . 1 . .
H H13A 0.8767 0.3469 0.4935 0.049 Uiso calc R 1 . .
H H13B 0.7579 0.5036 0.4844 0.049 Uiso calc R 1 . .
C C9 0.5685(3) 0.3119(2) 0.44757(16) 0.0346(4) Uani d . 1 . .
C C10 0.7206(3) 0.4014(3) 0.26241(17) 0.0419(5) Uani d . 1 . .
H H10A 0.6474 0.4861 0.2112 0.050 Uiso calc R 1 . .
H H10B 0.7122 0.3092 0.2429 0.050 Uiso calc R 1 . .
C C14 0.3260(3) 0.5119(2) 0.24945(17) 0.0400(5) Uani d . 1 . .
H H14 0.3266 0.5642 0.3041 0.048 Uiso calc R 1 . .
C C15 0.3794(3) 0.2783(3) 0.1980(2) 0.0505(6) Uani d . 1 . .
H H15 0.4169 0.1740 0.2178 0.061 Uiso calc R 1 . .
C C6 0.2442(3) 0.0770(2) 0.66839(18) 0.0407(5) Uani d . 1 . .
C C8 0.3242(3) 0.1861(2) 0.45921(18) 0.0404(5) Uani d . 1 . .
C C3 0.0878(3) 0.0243(3) 0.6458(2) 0.0483(6) Uani d . 1 . .
H H3A 0.1178 -0.0747 0.6326 0.058 Uiso calc R 1 . .
H H3B 0.0316 0.0940 0.5769 0.058 Uiso calc R 1 . .
C C4 0.2990(3) 0.0722(3) 0.77344(19) 0.0460(5) Uani d . 1 . .
C C11 0.8993(3) 0.4273(3) 0.25634(19) 0.0491(6) Uani d . 1 . .
H H11A 0.9223 0.4878 0.1807 0.059 Uiso calc R 1 . .
H H11B 0.9775 0.3318 0.2752 0.059 Uiso calc R 1 . .
C C12 0.9097(3) 0.5119(3) 0.34500(19) 0.0479(6) Uani d . 1 . .
H H12A 1.0244 0.5019 0.3700 0.057 Uiso calc R 1 . .
H H12B 0.8620 0.6186 0.3150 0.057 Uiso calc R 1 . .
C C18 0.2692(3) 0.5888(3) 0.13848(19) 0.0523(6) Uani d . 1 . .
H H18 0.2326 0.6933 0.1183 0.063 Uiso calc R 1 . .
C C1 -0.0312(3) 0.0142(3) 0.7442(2) 0.0656(7) Uani d . 1 . .
H H1A -0.1244 -0.0294 0.7287 0.079 Uiso calc R 1 . .
H H1B -0.0750 0.1156 0.7496 0.079 Uiso calc R 1 . .
C C17 0.2670(4) 0.5117(4) 0.0587(2) 0.0652(8) Uani d . 1 . .
H H17 0.2289 0.5640 -0.0157 0.078 Uiso calc R 1 . .
C C2 0.2226(4) 0.0138(3) 0.8875(2) 0.0639(7) Uani d . 1 . .
H H2A 0.1707 0.0990 0.9146 0.077 Uiso calc R 1 . .
H H2B 0.3099 -0.0470 0.9425 0.077 Uiso calc R 1 . .
C C16 0.3206(4) 0.3571(4) 0.0874(2) 0.0660(8) Uani d . 1 . .
H H16 0.3174 0.3053 0.0328 0.079 Uiso calc R 1 . .
C C19 0.3813(2) 0.3578(2) 0.27804(16) 0.0362(5) 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
C5 S1 C4 . . 91.10(10) ?
C1 S2 C2 . . 98.80(10) ?
C9 N1 C5 . . 115.5(2) ?
C9 N3 C8 . . 122.0(2) ?
C9 N3 C19 . . 122.1(2) ?
C8 N3 C19 . . 114.7(2) ?
C9 N2 C13 . . 118.4(2) ?
C9 N2 C10 . . 128.8(2) ?
C13 N2 C10 . . 110.9(2) ?
C5 C7 C8 . . 117.7(2) ?
C5 C7 C6 . . 113.8(2) ?
C8 C7 C6 . . 128.2(2) ?
N1 C5 C7 . . 127.4(2) ?
N1 C5 S1 . . 121.8(2) ?
C7 C5 S1 . . 110.8(2) ?
N2 C13 C12 . . 103.8(2) ?
N2 C13 H13A . . 111.0 ?
C12 C13 H13A . . 111.0 ?
N2 C13 H13B . . 111.0 ?
C12 C13 H13B . . 111.0 ?
H13A C13 H13B . . 109.0 ?
N1 C9 N2 . . 117.2(2) ?
N1 C9 N3 . . 122.8(2) ?
N2 C9 N3 . . 120.0(2) ?
N2 C10 C11 . . 103.5(2) ?
N2 C10 H10A . . 111.1 ?
C11 C10 H10A . . 111.1 ?
N2 C10 H10B . . 111.1 ?
C11 C10 H10B . . 111.1 ?
H10A C10 H10B . . 109.0 ?
C19 C14 C18 . . 119.4(2) ?
C19 C14 H14 . . 120.3 ?
C18 C14 H14 . . 120.3 ?
C19 C15 C16 . . 118.8(2) ?
C19 C15 H15 . . 120.6 ?
C16 C15 H15 . . 120.6 ?
C4 C6 C7 . . 111.3(2) ?
C4 C6 C3 . . 124.3(2) ?
C7 C6 C3 . . 124.3(2) ?
O1 C8 C7 . . 126.3(2) ?
O1 C8 N3 . . 119.5(2) ?
C7 C8 N3 . . 114.1(2) ?
C6 C3 C1 . . 112.4(2) ?
C6 C3 H3A . . 109.1 ?
C1 C3 H3A . . 109.1 ?
C6 C3 H3B . . 109.1 ?
C1 C3 H3B . . 109.1 ?
H3A C3 H3B . . 107.9 ?
C6 C4 C2 . . 128.5(2) ?
C6 C4 S1 . . 113.0(2) ?
C2 C4 S1 . . 118.5(2) ?
C10 C11 C12 . . 103.6(2) ?
C10 C11 H11A . . 111.0 ?
C12 C11 H11A . . 111.0 ?
C10 C11 H11B . . 111.0 ?
C12 C11 H11B . . 111.0 ?
H11A C11 H11B . . 109.0 ?
C13 C12 C11 . . 103.2(2) ?
C13 C12 H12A . . 111.1 ?
C11 C12 H12A . . 111.1 ?
C13 C12 H12B . . 111.1 ?
C11 C12 H12B . . 111.1 ?
H12A C12 H12B . . 109.1 ?
C17 C18 C14 . . 120.2(2) ?
C17 C18 H18 . . 119.9 ?
C14 C18 H18 . . 119.9 ?
C3 C1 S2 . . 112.3(2) ?
C3 C1 H1A . . 109.2 ?
S2 C1 H1A . . 109.2 ?
C3 C1 H1B . . 109.2 ?
S2 C1 H1B . . 109.2 ?
H1A C1 H1B . . 107.9 ?
C18 C17 C16 . . 120.5(2) ?
C18 C17 H17 . . 119.7 ?
C16 C17 H17 . . 119.7 ?
C4 C2 S2 . . 111.9(2) ?
C4 C2 H2A . . 109.2 ?
S2 C2 H2A . . 109.2 ?
C4 C2 H2B . . 109.2 ?
S2 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
C17 C16 C15 . . 120.1(2) ?
C17 C16 H16 . . 119.9 ?
C15 C16 H16 . . 119.9 ?
C14 C19 C15 . . 121.0(2) ?
C14 C19 N3 . . 118.9(2) ?
C15 C19 N3 . . 120.1(2) ?
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
S1 C5 . 1.736(2) ?
S1 C4 . 1.750(2) ?
S2 C1 . 1.801(3) ?
S2 C2 . 1.803(3) ?
N1 C9 . 1.320(3) ?
N1 C5 . 1.352(3) ?
N3 C9 . 1.392(3) ?
N3 C8 . 1.432(3) ?
N3 C19 . 1.451(2) ?
N2 C9 . 1.350(3) ?
N2 C13 . 1.473(2) ?
N2 C10 . 1.477(2) ?
O1 C8 . 1.220(3) ?
C7 C5 . 1.379(3) ?
C7 C8 . 1.427(3) ?
C7 C6 . 1.442(3) ?
C13 C12 . 1.513(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C10 C11 . 1.516(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C14 C19 . 1.375(3) ?
C14 C18 . 1.386(3) ?
C14 H14 . 0.9300 ?
C15 C19 . 1.385(3) ?
C15 C16 . 1.390(4) ?
C15 H15 . 0.9300 ?
C6 C4 . 1.352(3) ?
C6 C3 . 1.504(3) ?
C3 C1 . 1.517(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C2 . 1.507(3) ?
C11 C12 . 1.519(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C18 C17 . 1.366(4) ?
C18 H18 . 0.9300 ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C17 C16 . 1.377(4) ?
C17 H17 . 0.9300 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C16 H16 . 0.9300 ?
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
_geom_hbond_publ_flag
C11 H11B O1 1_655 0.97 2.58 3.434(3) 147.6 y
C1 H1A O1 2_556 0.97 2.48 3.287(3) 140.3 y
C3 H3B O1 . 0.97 2.50 3.038(3) 114.7 ?
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
C9 N1 C5 C7 . . . . 4.1(3) ?
C9 N1 C5 S1 . . . . -175.1(2) ?
C8 C7 C5 N1 . . . . -3.7(3) ?
C6 C7 C5 N1 . . . . -177.4(2) ?
C8 C7 C5 S1 . . . . 175.5(2) ?
C6 C7 C5 S1 . . . . 1.9(2) ?
C4 S1 C5 N1 . . . . 178.0(2) ?
C4 S1 C5 C7 . . . . -1.3(2) ?
C9 N2 C13 C12 . . . . 178.6(2) ?
C10 N2 C13 C12 . . . . 13.1(2) ?
C5 N1 C9 N2 . . . . 179.8(2) ?
C5 N1 C9 N3 . . . . 1.5(3) ?
C13 N2 C9 N1 . . . . -4.0(3) ?
C10 N2 C9 N1 . . . . 158.6(2) ?
C13 N2 C9 N3 . . . . 174.4(2) ?
C10 N2 C9 N3 . . . . -23.0(3) ?
C8 N3 C9 N1 . . . . -7.1(3) ?
C19 N3 C9 N1 . . . . 159.5(2) ?
C8 N3 C9 N2 . . . . 174.5(2) ?
C19 N3 C9 N2 . . . . -18.8(3) ?
C9 N2 C10 C11 . . . . -152.5(2) ?
C13 N2 C10 C11 . . . . 11.2(2) ?
C5 C7 C6 C4 . . . . -1.6(3) ?
C8 C7 C6 C4 . . . . -174.4(2) ?
C5 C7 C6 C3 . . . . 174.4(2) ?
C8 C7 C6 C3 . . . . 1.6(4) ?
C5 C7 C8 O1 . . . . -178.3(2) ?
C6 C7 C8 O1 . . . . -5.7(4) ?
C5 C7 C8 N3 . . . . -1.9(3) ?
C6 C7 C8 N3 . . . . 170.6(2) ?
C9 N3 C8 O1 . . . . -176.4(2) ?
C19 N3 C8 O1 . . . . 16.0(3) ?
C9 N3 C8 C7 . . . . 7.0(3) ?
C19 N3 C8 C7 . . . . -160.6(2) ?
C4 C6 C3 C1 . . . . 19.0(3) ?
C7 C6 C3 C1 . . . . -156.5(2) ?
C7 C6 C4 C2 . . . . 177.0(2) ?
C3 C6 C4 C2 . . . . 1.0(4) ?
C7 C6 C4 S1 . . . . 0.6(3) ?
C3 C6 C4 S1 . . . . -175.5(2) ?
C5 S1 C4 C6 . . . . 0.4(2) ?
C5 S1 C4 C2 . . . . -176.4(2) ?
N2 C10 C11 C12 . . . . -30.9(2) ?
N2 C13 C12 C11 . . . . -31.9(2) ?
C10 C11 C12 C13 . . . . 39.2(2) ?
C19 C14 C18 C17 . . . . 0.6(3) ?
C6 C3 C1 S2 . . . . -53.3(3) ?
C2 S2 C1 C3 . . . . 62.2(2) ?
C14 C18 C17 C16 . . . . 0.1(4) ?
C6 C4 C2 S2 . . . . 14.9(4) ?
S1 C4 C2 S2 . . . . -168.8(2) ?
C1 S2 C2 C4 . . . . -40.8(2) ?
C18 C17 C16 C15 . . . . -0.7(4) ?
C19 C15 C16 C17 . . . . 0.7(4) ?
C18 C14 C19 C15 . . . . -0.7(3) ?
C18 C14 C19 N3 . . . . -178.4(2) ?
C16 C15 C19 C14 . . . . 0.1(3) ?
C16 C15 C19 N3 . . . . 177.7(2) ?
C9 N3 C19 C14 . . . . -60.2(3) ?
C8 N3 C19 C14 . . . . 107.4(2) ?
C9 N3 C19 C15 . . . . 122.1(2) ?
C8 N3 C19 C15 . . . . -70.3(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745816
