#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/52/4105207.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_4105207
loop_
_publ_author_name
'Zitao Wang'
'Yang Wang'
'Wen-Xiong Zhang'
'Zhaomin Hou'
'Zhenfeng Xi'
_publ_section_title
;
 Efficient One-Pot Synthesis of 2,3-Dihydropyrimidinthiones via
 Multicomponent Coupling of Terminal Alkynes, Elemental Sulfur, and
 Carbodiimides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15108
_journal_page_last               15109
_journal_paper_doi               10.1021/ja9069419
_journal_volume                  131
_journal_year                    2009
_chemical_formula_sum            'C15 H20 N2 S'
_chemical_formula_weight         260.39
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   12.589(2)
_cell_length_b                   14.928(3)
_cell_length_c                   15.567(3)
_cell_measurement_temperature    173(2)
_cell_volume                     2925.5(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14386
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.9598
_exptl_absorpt_correction_T_min  0.9311
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2591
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0379
_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)+(0.0200P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0713
_reflns_number_gt                1607
_reflns_number_total             2591
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9069419_si_001.cif
_cod_data_source_block           1a
_cod_original_cell_volume        2925.4(9)
_cod_database_code               4105207
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'
'-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_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.09271(15) 0.04356(14) 0.70757(11) 0.0407(5) Uani 1 1 d .
C2 C 0.22395(14) 0.15530(13) 0.67673(12) 0.0381(5) Uani 1 1 d .
H2 H 0.2693 0.2016 0.6969 0.046 Uiso 1 1 calc R
C3 C 0.24548(14) 0.12011(13) 0.59745(11) 0.0330(5) Uani 1 1 d .
C4 C 0.16519(14) 0.06371(12) 0.55999(11) 0.0331(5) Uani 1 1 d .
C5 C 0.33667(14) 0.15677(13) 0.54796(12) 0.0350(5) Uani 1 1 d .
C6 C 0.35538(15) 0.24827(14) 0.54659(12) 0.0460(6) Uani 1 1 d .
H6 H 0.3088 0.2871 0.5769 0.055 Uiso 1 1 calc R
C7 C 0.44037(19) 0.28440(17) 0.50208(14) 0.0581(7) Uani 1 1 d .
H7 H 0.4520 0.3473 0.5021 0.070 Uiso 1 1 calc R
C8 C 0.50790(18) 0.22865(19) 0.45782(15) 0.0624(7) Uani 1 1 d .
H8 H 0.5667 0.2529 0.4274 0.075 Uiso 1 1 calc R
C9 C 0.49039(17) 0.13817(18) 0.45765(14) 0.0623(7) Uani 1 1 d .
H9 H 0.5369 0.0998 0.4268 0.075 Uiso 1 1 calc R
C10 C 0.40508(16) 0.10202(15) 0.50232(13) 0.0495(6) Uani 1 1 d .
H10 H 0.3936 0.0391 0.5015 0.059 Uiso 1 1 calc R
C11 C 0.16039(17) -0.03330(15) 0.74237(13) 0.0616(7) Uani 1 1 d .
H11A H 0.1284 -0.0906 0.7259 0.092 Uiso 1 1 calc R
H11B H 0.1640 -0.0293 0.8051 0.092 Uiso 1 1 calc R
H11C H 0.2322 -0.0293 0.7184 0.092 Uiso 1 1 calc R
C12 C -0.02138(15) 0.03806(16) 0.74117(13) 0.0608(7) Uani 1 1 d .
H12A H -0.0617 0.0901 0.7210 0.091 Uiso 1 1 calc R
H12B H -0.0206 0.0374 0.8041 0.091 Uiso 1 1 calc R
H12C H -0.0549 -0.0169 0.7199 0.091 Uiso 1 1 calc R
C13 C 0.11939(18) 0.18301(16) 0.80674(13) 0.0479(6) Uani 1 1 d .
C14 C 0.21533(18) 0.19354(17) 0.86400(14) 0.0807(9) Uani 1 1 d .
H14A H 0.2696 0.2289 0.8341 0.121 Uiso 1 1 calc R
H14B H 0.2441 0.1343 0.8780 0.121 Uiso 1 1 calc R
H14C H 0.1946 0.2243 0.9170 0.121 Uiso 1 1 calc R
C15 C 0.0721(2) 0.27227(17) 0.78263(13) 0.0817(9) Uani 1 1 d .
H15A H 0.1237 0.3065 0.7487 0.123 Uiso 1 1 calc R
H15B H 0.0543 0.3057 0.8349 0.123 Uiso 1 1 calc R
H15C H 0.0076 0.2627 0.7486 0.123 Uiso 1 1 calc R
H1 H 0.0290(15) 0.0125(12) 0.5902(11) 0.056(7) Uiso 1 1 d .
H13 H 0.0670(15) 0.1482(13) 0.8388(11) 0.058(7) Uiso 1 1 d .
N1 N 0.08690(13) 0.03858(11) 0.61361(10) 0.0379(4) Uani 1 1 d .
N2 N 0.14412(12) 0.12978(11) 0.72820(9) 0.0399(4) Uani 1 1 d .
S1 S 0.15739(4) 0.03904(4) 0.45483(3) 0.04775(18) Uani 1 1 d .
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'
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
N1 C1 N2 106.45(15)
N1 C1 C11 110.08(17)
N2 C1 C11 109.45(16)
N1 C1 C12 106.94(16)
N2 C1 C12 112.57(17)
C11 C1 C12 111.20(17)
N2 C2 C3 125.34(19)
C2 C3 C4 116.81(17)
C2 C3 C5 118.61(18)
C4 C3 C5 123.21(16)
N1 C4 C3 115.25(16)
N1 C4 S1 120.03(14)
C3 C4 S1 124.33(14)
C10 C5 C6 117.93(19)
C10 C5 C3 121.95(18)
C6 C5 C3 120.12(18)
C7 C6 C5 121.5(2)
C8 C7 C6 119.5(2)
C9 C8 C7 119.9(2)
C8 C9 C10 120.5(2)
C5 C10 C9 120.6(2)
N2 C13 C15 110.46(17)
N2 C13 C14 111.88(18)
C15 C13 C14 111.8(2)
C4 N1 C1 124.63(17)
C2 N2 C1 116.52(15)
C2 N2 C13 119.68(18)
C1 N2 C13 123.48(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.466(2)
C1 N2 1.476(2)
C1 C11 1.528(3)
C1 C12 1.531(2)
C2 N2 1.341(2)
C2 C3 1.368(2)
C3 C4 1.439(2)
C3 C5 1.487(2)
C4 N1 1.345(2)
C4 S1 1.6809(18)
C5 C10 1.384(3)
C5 C6 1.386(3)
C6 C7 1.384(3)
C7 C8 1.375(3)
C8 C9 1.369(3)
C9 C10 1.389(3)
C13 N2 1.491(2)
C13 C15 1.507(3)
C13 C14 1.509(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660215
