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#$Date: 2023-01-17 12:25:31 +0200 (Tue, 17 Jan 2023) $
#$Revision: 280383 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/64/8106488.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_8106488
loop_
_publ_author_name
'Al-Jaeed, Nada'
'Lahsasni, Siham'
'Ghabbour, Hazem A.'
'El-Sayed, Nahed N. E.'
_publ_section_title
;
 Crystal structure of
 N,N-dimethyl-N′-(2-methyl-4-oxo-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-3(4H)-yl)formimidamide,
 C14H18N4OS
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              217
_journal_page_last               219
_journal_paper_doi               10.1515/ncrs-2016-0212
_journal_volume                  232
_journal_year                    2017
_chemical_formula_sum            'C14 H18 N4 O S'
_chemical_formula_weight         290.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 99.385(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.479(4)
_cell_length_b                   13.203(3)
_cell_length_c                   7.3147(17)
_cell_measurement_reflns_used    3006
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.46
_cell_measurement_theta_min      2.67
_cell_volume                     1474.9(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2586
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.667
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.9733
_exptl_absorpt_correction_T_min  0.8579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS_Bruker_2014
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.715
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0973
_refine_ls_R_factor_gt           0.0704
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0678P)²+1.6408P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1823
_refine_ls_wR_factor_ref         0.1968
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1843
_reflns_number_total             2586
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2016-0212_suppl.cif
_cod_data_source_block           t
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8106488
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.858
_shelx_estimated_absorpt_t_max   0.973
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.95126(6) 0.60043(9) 0.72694(17) 0.0482(4) Uani 1 1 d . . . . .
O1 O 0.64840(17) 0.6223(2) 0.3825(4) 0.0463(8) Uani 1 1 d . . . . .
N1 N 0.8650(2) 0.7765(3) 0.6372(5) 0.0410(9) Uani 1 1 d . . . . .
N2 N 0.72087(18) 0.7696(3) 0.4752(4) 0.0343(8) Uani 1 1 d . . . . .
N3 N 0.6511(2) 0.8268(3) 0.3738(5) 0.0424(9) Uani 1 1 d . . . . .
N4 N 0.5092(2) 0.8706(3) 0.3810(6) 0.0593(12) Uani 1 1 d . . . . .
C1 C 0.8943(3) 0.4899(3) 0.6610(6) 0.0433(11) Uani 1 1 d . . . . .
C2 C 0.9333(3) 0.3872(4) 0.7080(7) 0.0587(13) Uani 1 1 d . . . . .
H2A H 0.9376 0.3749 0.8427 0.070 Uiso 1 1 calc R U . . .
H2B H 0.9930 0.3844 0.6764 0.070 Uiso 1 1 calc R U . . .
C3 C 0.8770(3) 0.3065(4) 0.6019(8) 0.0678(15) Uani 1 1 d . . . . .
H3A H 0.8868 0.3065 0.4714 0.081 Uiso 1 1 calc R U . . .
H3B H 0.8945 0.2394 0.6558 0.081 Uiso 1 1 calc R U . . .
C4 C 0.7813(3) 0.3236(4) 0.6070(9) 0.0668(15) Uani 1 1 d . . . . .
H4A H 0.7718 0.3245 0.7376 0.080 Uiso 1 1 calc R U . . .
H4B H 0.7471 0.2667 0.5437 0.080 Uiso 1 1 calc R U . . .
C5 C 0.7482(3) 0.4231(3) 0.5138(7) 0.0533(12) Uani 1 1 d . . . . .
H5A H 0.7408 0.4151 0.3775 0.064 Uiso 1 1 calc R U . . .
H5B H 0.6904 0.4399 0.5471 0.064 Uiso 1 1 calc R U . . .
C6 C 0.8115(2) 0.5081(3) 0.5732(5) 0.0373(10) Uani 1 1 d . . . . .
C7 C 0.7938(2) 0.6140(3) 0.5538(5) 0.0336(9) Uani 1 1 d . . . . .
C8 C 0.8623(2) 0.6739(3) 0.6303(5) 0.0374(10) Uani 1 1 d . . . . .
C9 C 0.7148(2) 0.6632(3) 0.4638(5) 0.0337(9) Uani 1 1 d . . . . .
C10 C 0.7940(3) 0.8218(3) 0.5583(6) 0.0375(10) Uani 1 1 d . . . . .
C11 C 0.7896(3) 0.9339(4) 0.5601(7) 0.0528(12) Uani 1 1 d . . . . .
H11A H 0.8456 0.9612 0.6223 0.079 Uiso 1 1 calc R U . . .
H11B H 0.7427 0.9555 0.6267 0.079 Uiso 1 1 calc R U . . .
H11C H 0.7776 0.9592 0.4325 0.079 Uiso 1 1 calc R U . . .
C12 C 0.5835(3) 0.8242(3) 0.4543(6) 0.0404(10) Uani 1 1 d . . . . .
H12A H 0.5863 0.7887 0.5681 0.048 Uiso 1 1 calc R U . . .
C13 C 0.4323(3) 0.8627(5) 0.4683(11) 0.092(2) Uani 1 1 d . . . . .
H13A H 0.4481 0.8316 0.5909 0.138 Uiso 1 1 calc R U . . .
H13B H 0.3883 0.8206 0.3917 0.138 Uiso 1 1 calc R U . . .
H13C H 0.4081 0.9304 0.4816 0.138 Uiso 1 1 calc R U . . .
C14 C 0.5008(4) 0.9215(5) 0.2023(8) 0.0788(18) Uani 1 1 d . . . . .
H14A H 0.5591 0.9327 0.1702 0.118 Uiso 1 1 calc R U . . .
H14B H 0.4714 0.9868 0.2093 0.118 Uiso 1 1 calc R U . . .
H14C H 0.4662 0.8793 0.1071 0.118 Uiso 1 1 calc R U . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
C1 S1 C8 91.3(2) . .
C10 N1 C8 115.1(3) . .
C10 N2 C9 124.5(3) . .
C10 N2 N3 117.6(3) . .
C9 N2 N3 117.4(3) . .
C12 N3 N2 110.7(3) . .
C12 N4 C13 120.5(5) . .
C12 N4 C14 121.1(4) . .
C13 N4 C14 118.1(4) . .
C6 C1 C2 125.5(4) . .
C6 C1 S1 112.4(3) . .
C2 C1 S1 122.0(3) . .
C1 C2 C3 110.1(4) . .
C1 C2 H2A 109.6 . .
C3 C2 H2A 109.6 . .
C1 C2 H2B 109.6 . .
C3 C2 H2B 109.6 . .
H2A C2 H2B 108.2 . .
C4 C3 C2 111.7(4) . .
C4 C3 H3A 109.3 . .
C2 C3 H3A 109.3 . .
C4 C3 H3B 109.3 . .
C2 C3 H3B 109.3 . .
H3A C3 H3B 107.9 . .
C3 C4 C5 112.2(4) . .
C3 C4 H4A 109.2 . .
C5 C4 H4A 109.2 . .
C3 C4 H4B 109.2 . .
C5 C4 H4B 109.2 . .
H4A C4 H4B 107.9 . .
C6 C5 C4 110.9(4) . .
C6 C5 H5A 109.5 . .
C4 C5 H5A 109.5 . .
C6 C5 H5B 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 108.1 . .
C1 C6 C7 111.8(4) . .
C1 C6 C5 121.6(4) . .
C7 C6 C5 126.6(3) . .
C8 C7 C6 113.7(3) . .
C8 C7 C9 117.9(4) . .
C6 C7 C9 128.3(3) . .
N1 C8 C7 127.6(4) . .
N1 C8 S1 121.6(3) . .
C7 C8 S1 110.7(3) . .
O1 C9 N2 120.7(3) . .
O1 C9 C7 127.1(4) . .
N2 C9 C7 112.2(3) . .
N1 C10 N2 122.7(4) . .
N1 C10 C11 119.4(4) . .
N2 C10 C11 117.9(4) . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
N3 C12 N4 121.1(4) . .
N3 C12 H12A 119.4 . .
N4 C12 H12A 119.4 . .
N4 C13 H13A 109.5 . .
N4 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
N4 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
N4 C14 H14A 109.5 . .
N4 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
N4 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.732(5) .
S1 C8 1.738(4) .
O1 C9 1.226(4) .
N1 C10 1.300(5) .
N1 C8 1.357(6) .
N2 C10 1.379(5) .
N2 C9 1.409(5) .
N2 N3 1.423(4) .
N3 C12 1.282(5) .
N4 C12 1.336(5) .
N4 C13 1.444(7) .
N4 C14 1.457(7) .
C1 C6 1.358(6) .
C1 C2 1.501(6) .
C2 C3 1.509(7) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.505(7) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.529(7) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.507(6) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 C7 1.427(6) .
C7 C8 1.366(5) .
C7 C9 1.445(5) .
C10 C11 1.482(6) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9500 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C10 N2 N3 C12 -112.7(4) . . . .
C9 N2 N3 C12 75.1(4) . . . .
C8 S1 C1 C6 -1.1(3) . . . .
C8 S1 C1 C2 -178.0(4) . . . .
C6 C1 C2 C3 14.8(7) . . . .
S1 C1 C2 C3 -168.8(4) . . . .
C1 C2 C3 C4 -45.0(6) . . . .
C2 C3 C4 C5 62.8(6) . . . .
C3 C4 C5 C6 -45.0(6) . . . .
C2 C1 C6 C7 178.3(4) . . . .
S1 C1 C6 C7 1.6(5) . . . .
C2 C1 C6 C5 0.5(7) . . . .
S1 C1 C6 C5 -176.2(4) . . . .
C4 C5 C6 C1 14.3(6) . . . .
C4 C5 C6 C7 -163.2(4) . . . .
C1 C6 C7 C8 -1.4(5) . . . .
C5 C6 C7 C8 176.3(4) . . . .
C1 C6 C7 C9 177.9(4) . . . .
C5 C6 C7 C9 -4.4(7) . . . .
C10 N1 C8 C7 -1.2(6) . . . .
C10 N1 C8 S1 179.6(3) . . . .
C6 C7 C8 N1 -178.7(4) . . . .
C9 C7 C8 N1 1.9(6) . . . .
C6 C7 C8 S1 0.6(4) . . . .
C9 C7 C8 S1 -178.8(3) . . . .
C1 S1 C8 N1 179.6(4) . . . .
C1 S1 C8 C7 0.3(3) . . . .
C10 N2 C9 O1 -177.7(4) . . . .
N3 N2 C9 O1 -6.1(5) . . . .
C10 N2 C9 C7 1.4(5) . . . .
N3 N2 C9 C7 173.0(3) . . . .
C8 C7 C9 O1 177.3(4) . . . .
C6 C7 C9 O1 -2.1(7) . . . .
C8 C7 C9 N2 -1.8(5) . . . .
C6 C7 C9 N2 178.9(4) . . . .
C8 N1 C10 N2 0.6(6) . . . .
C8 N1 C10 C11 179.2(4) . . . .
C9 N2 C10 N1 -0.9(6) . . . .
N3 N2 C10 N1 -172.5(4) . . . .
C9 N2 C10 C11 -179.5(4) . . . .
N3 N2 C10 C11 8.9(5) . . . .
N2 N3 C12 N4 -178.2(4) . . . .
C13 N4 C12 N3 176.8(5) . . . .
C14 N4 C12 N3 3.1(7) . . . .
