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#$Date: 2017-09-18 11:55:08 +0300 (Mon, 18 Sep 2017) $
#$Revision: 200974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/72/1547209.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_1547209
loop_
_publ_author_name
'Behrooz Rezaei'
'Mehrnoosh Fazlollahi'
_publ_section_title
;
 Synthesis, solvatochromism and crystal structure of
 5-Methoxy-5,6-diphenyl-4,5-dihydro-2H -1,2,4-triazine-3-thione
;
_journal_name_full               'Chemistry Central Journal'
_journal_page_first              130
_journal_paper_doi               10.1186/1752-153X-7-130
_journal_volume                  7
_journal_year                    2013
_chemical_formula_sum            'C16 H15 N3 O S'
_chemical_formula_weight         297.37
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 101.290(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6990(10)
_cell_length_b                   8.5000(10)
_cell_length_c                   18.044(2)
_cell_measurement_temperature    193(2)
_cell_volume                     1458.8(3)
_computing_data_collection       STOE-X-AREA
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  STOE-IPDSII
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10112
_diffrn_reflns_theta_full        25.66
_diffrn_reflns_theta_max         25.66
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.224
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.062(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         2618
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0371
_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)+(0.0541P)²+0.5730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                2456
_reflns_number_total             2618
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            13065_2013_668_MOESM1_ESM.txt
_cod_data_source_block           k125m
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1547209
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.06964(15) 0.37927(16) 0.78966(9) 0.0228(3) Uani 1 1 d . . .
C2 C -0.18246(14) 0.23911(16) 0.88410(8) 0.0213(3) Uani 1 1 d . . .
C4 C 0.04476(17) 0.1973(2) 0.96038(12) 0.0354(4) Uani 1 1 d . . .
C5 C -0.32689(14) 0.16213(17) 0.86545(9) 0.0221(3) Uani 1 1 d . . .
C6 C -0.36613(16) 0.04406(18) 0.91049(10) 0.0288(4) Uani 1 1 d . . .
C7 C -0.50083(17) -0.0187(2) 0.89344(11) 0.0349(4) Uani 1 1 d . . .
C8 C -0.59658(17) 0.0366(2) 0.83231(11) 0.0349(4) Uani 1 1 d . . .
C9 C -0.55775(18) 0.1524(2) 0.78698(11) 0.0358(4) Uani 1 1 d . . .
C10 C -0.42309(17) 0.21477(19) 0.80362(10) 0.0290(4) Uani 1 1 d . . .
C11 C -0.19281(14) 0.40531(17) 0.91525(9) 0.0219(3) Uani 1 1 d . . .
C12 C -0.25169(14) 0.43365(18) 0.98398(9) 0.0233(3) Uani 1 1 d . . .
C13 C -0.23035(16) 0.3307(2) 1.04543(9) 0.0286(4) Uani 1 1 d . . .
C14 C -0.27710(18) 0.3707(2) 1.11095(10) 0.0329(4) Uani 1 1 d . . .
C15 C -0.34636(17) 0.5101(2) 1.11613(10) 0.0344(4) Uani 1 1 d . . .
C16 C -0.37007(17) 0.6122(2) 1.05509(11) 0.0326(4) Uani 1 1 d . . .
C17 C -0.32354(15) 0.57418(19) 0.98958(10) 0.0270(3) Uani 1 1 d . . .
N1 N -0.12371(13) 0.25086(15) 0.81527(8) 0.0243(3) Uani 1 1 d . . .
N2 N -0.09079(14) 0.51458(15) 0.82340(8) 0.0279(3) Uani 1 1 d . . .
N3 N -0.15048(13) 0.52984(14) 0.88577(8) 0.0252(3) Uani 1 1 d . . .
S1 S 0.01610(4) 0.37904(4) 0.71653(2) 0.02953(17) Uani 1 1 d . . .
O1 O -0.09594(10) 0.14099(12) 0.93642(6) 0.0248(3) Uani 1 1 d . . .
H1 H -0.1041(19) 0.164(2) 0.7983(11) 0.029(5) Uiso 1 1 d . . .
H2 H -0.057(2) 0.607(2) 0.8071(11) 0.030(5) Uiso 1 1 d . . .
H6 H -0.301(2) 0.008(2) 0.9538(12) 0.034(5) Uiso 1 1 d . . .
H7 H -0.527(2) -0.095(3) 0.9254(12) 0.044(6) Uiso 1 1 d . . .
H8 H -0.688(2) -0.004(2) 0.8213(12) 0.045(6) Uiso 1 1 d . . .
H9 H -0.622(2) 0.193(3) 0.7442(12) 0.043(5) Uiso 1 1 d . . .
H10 H -0.3996(19) 0.296(2) 0.7725(11) 0.033(5) Uiso 1 1 d . . .
H13 H -0.180(2) 0.239(2) 1.0437(11) 0.032(5) Uiso 1 1 d . . .
H14 H -0.2583(19) 0.305(2) 1.1543(11) 0.031(5) Uiso 1 1 d . . .
H15 H -0.373(2) 0.539(2) 1.1631(13) 0.042(5) Uiso 1 1 d . . .
H16 H -0.421(2) 0.712(3) 1.0568(12) 0.040(5) Uiso 1 1 d . . .
H17 H -0.3430(18) 0.641(2) 0.9466(11) 0.026(4) Uiso 1 1 d . . .
H41 H 0.043(3) 0.307(3) 0.9752(15) 0.068(8) Uiso 1 1 d . . .
H42 H 0.085(3) 0.135(3) 1.0030(15) 0.056(7) Uiso 1 1 d . . .
H43 H 0.092(3) 0.193(3) 0.9170(16) 0.072(8) Uiso 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'
O O 0.0106 0.0060 '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
N1 C1 N2 116.19(14) . .
N1 C1 S1 123.82(11) . .
N2 C1 S1 119.94(11) . .
O1 C2 N1 109.19(11) . .
O1 C2 C5 107.19(11) . .
N1 C2 C5 109.57(12) . .
O1 C2 C11 111.96(12) . .
N1 C2 C11 108.18(11) . .
C5 C2 C11 110.73(11) . .
C10 C5 C6 119.14(14) . .
C10 C5 C2 119.08(13) . .
C6 C5 C2 121.74(14) . .
C7 C6 C5 120.06(16) . .
C8 C7 C6 120.25(16) . .
C9 C8 C7 119.92(15) . .
C8 C9 C10 119.96(17) . .
C5 C10 C9 120.65(16) . .
N3 C11 C12 114.71(13) . .
N3 C11 C2 123.91(13) . .
C12 C11 C2 121.37(12) . .
C13 C12 C17 118.51(14) . .
C13 C12 C11 122.74(13) . .
C17 C12 C11 118.61(14) . .
C14 C13 C12 120.02(15) . .
C15 C14 C13 120.95(16) . .
C14 C15 C16 119.54(15) . .
C17 C16 C15 120.14(15) . .
C16 C17 C12 120.82(15) . .
C1 N1 C2 126.42(13) . .
C1 N2 N3 125.71(13) . .
C11 N3 N2 118.83(13) . .
C2 O1 C4 114.37(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.3321(19) .
C1 N2 1.3358(19) .
C1 S1 1.6920(16) .
C2 O1 1.4075(17) .
C2 N1 1.4678(18) .
C2 C5 1.5229(19) .
C2 C11 1.5309(19) .
C4 O1 1.4308(18) .
C5 C10 1.381(2) .
C5 C6 1.391(2) .
C6 C7 1.389(2) .
C7 C8 1.378(3) .
C8 C9 1.379(3) .
C9 C10 1.387(2) .
C11 N3 1.2875(19) .
C11 C12 1.483(2) .
C12 C13 1.396(2) .
C12 C17 1.397(2) .
C13 C14 1.389(2) .
C14 C15 1.375(2) .
C15 C16 1.385(3) .
C16 C17 1.383(2) .
N2 N3 1.3688(18) .
