#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:32:13 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230515 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/77/7057754.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_7057754
loop_
_publ_author_name
'Ramezanpour, Sorour'
'Rezaei, Mohammad Nasim'
'Vaezghaemi, Aref'
'Rominger, Frank'
_publ_section_title
;
 Facile synthesis of novel 3,4,5-trisubstituted-1,2,4-triazin-6(1H)-ones
 via a sequential Ugi--Smiles type/nucleophilic substitution/cyclization
 reaction
;
_journal_issue                   21
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17533
_journal_paper_doi               10.1039/C8NJ03949F
_journal_volume                  42
_journal_year                    2018
_chemical_formula_sum            'C10 H11 N3 O2 S'
_chemical_formula_weight         237.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-04-11 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.8951(11)
_cell_length_b                   6.7525(4)
_cell_length_c                   8.0436(4)
_cell_measurement_reflns_used    1594
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.90
_cell_measurement_theta_min      2.73
_cell_volume                     1080.59(10)
_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-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6871
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.691
_diffrn_reflns_theta_min         2.047
_diffrn_source                   'ImuS microsource'
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.9582
_exptl_absorpt_correction_T_min  0.8363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     99
_refine_ls_number_reflns         1122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0401
_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)+(0.0439P)²+0.6305P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1019
_reflns_Friedel_coverage         0.000
_reflns_number_gt                919
_reflns_number_total             1122
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj03949f2.cif
_cod_data_source_block           sba153
_cod_depositor_comments
'Adding full bibliography for 7057752--7057754.cif.'
_cod_database_code               7057754
_shelx_shelxl_version_number     2016/6
_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   0.914
_shelx_estimated_absorpt_t_max   0.986
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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
S1 S 0.38482(4) 0.750000 0.40095(9) 0.0284(2) Uani 1 2 d S T P
O11 O 0.35063(7) 0.5697(2) 0.35737(18) 0.0375(4) Uani 1 1 d . . .
N2 N 0.46032(12) 0.750000 0.3234(3) 0.0296(6) Uani 1 2 d S T P
C3 C 0.50458(14) 0.750000 0.4437(3) 0.0242(6) Uani 1 2 d S T P
N4 N 0.57053(12) 0.750000 0.4152(3) 0.0274(6) Uani 1 2 d S T P
H4 H 0.5969(15) 0.750000 0.492(4) 0.024(8) Uiso 1 2 d S . P
N5 N 0.59338(12) 0.750000 0.2525(3) 0.0331(6) Uani 1 2 d S T P
C6 C 0.65742(15) 0.750000 0.2309(4) 0.0324(7) Uani 1 2 d S T P
C7 C 0.71043(16) 0.750000 0.3624(4) 0.0409(8) Uani 1 2 d S T P
H7A H 0.723206 0.886743 0.388241 0.061 Uiso 0.5 1 calc R U P
H7B H 0.749896 0.677375 0.322409 0.061 Uiso 0.5 1 calc R U P
H7C H 0.692975 0.685881 0.462807 0.061 Uiso 0.5 1 calc R U P
C8 C 0.68036(18) 0.750000 0.0541(4) 0.0513(10) Uani 1 2 d S T P
H8A H 0.719773 0.664010 0.042731 0.077 Uiso 0.5 1 calc R U P
H8B H 0.692244 0.885171 0.020878 0.077 Uiso 0.5 1 calc R U P
H8C H 0.644112 0.700819 -0.017333 0.077 Uiso 0.5 1 calc R U P
C11 C 0.40862(15) 0.750000 0.6131(4) 0.0275(7) Uani 1 2 d S T P
C12 C 0.47856(14) 0.750000 0.6168(3) 0.0255(6) Uani 1 2 d S T P
C13 C 0.51154(16) 0.750000 0.7676(4) 0.0319(7) Uani 1 2 d S T P
H13 H 0.559259 0.750000 0.772045 0.038 Uiso 1 2 calc R U P
C14 C 0.47405(17) 0.750000 0.9122(4) 0.0374(8) Uani 1 2 d S T P
H14 H 0.496175 0.750000 1.016823 0.045 Uiso 1 2 calc R U P
C15 C 0.40424(17) 0.750000 0.9058(4) 0.0390(8) Uani 1 2 d S T P
H15 H 0.379312 0.750000 1.006567 0.047 Uiso 1 2 calc R U P
C16 C 0.37026(16) 0.750000 0.7552(4) 0.0344(7) Uani 1 2 d S T P
H16 H 0.322550 0.750000 0.750493 0.041 Uiso 1 2 calc R U P
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
O11 S1 O11 115.69(13) 7_575 .
O11 S1 N2 110.08(8) 7_575 .
O11 S1 N2 110.08(8) . .
O11 S1 C11 111.19(8) 7_575 .
O11 S1 C11 111.19(8) . .
N2 S1 C11 97.05(13) . .
C3 N2 S1 109.7(2) . .
N2 C3 N4 122.4(3) . .
N2 C3 C12 117.3(2) . .
N4 C3 C12 120.3(2) . .
C3 N4 N5 119.1(3) . .
C3 N4 H4 121(2) . .
N5 N4 H4 120(2) . .
C6 N5 N4 116.9(3) . .
N5 C6 C8 115.6(3) . .
N5 C6 C7 127.1(3) . .
C8 C6 C7 117.3(3) . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C6 C7 H7A 109.47(3) . 7_575
H7A C7 H7A 140.8 . 7_575
H7B C7 H7A 52.4 . 7_575
H7C C7 H7A 60.1 . 7_575
C6 C7 H7B 109.5(4) . 7_575
H7A C7 H7B 52.4 . 7_575
H7B C7 H7B 60.1 . 7_575
H7C C7 H7B 140.9 . 7_575
H7A C7 H7B 109.5 7_575 7_575
C6 C7 H7C 109.5(4) . 7_575
H7A C7 H7C 60.1 . 7_575
H7B C7 H7C 140.8 . 7_575
H7C C7 H7C 52.4 . 7_575
H7A C7 H7C 109.5 7_575 7_575
H7B C7 H7C 109.5 7_575 7_575
C6 C8 H8A 109.5 . .
C6 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C6 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C6 C8 H8A 109.5(5) . 7_575
H8A C8 H8A 72.7 . 7_575
H8B C8 H8A 39.6 . 7_575
H8C C8 H8A 137.3 . 7_575
C6 C8 H8B 109.47(16) . 7_575
H8A C8 H8B 39.6 . 7_575
H8B C8 H8B 137.3 . 7_575
H8C C8 H8B 72.7 . 7_575
H8A C8 H8B 109.5 7_575 7_575
C6 C8 H8C 109.5(4) . 7_575
H8A C8 H8C 137.3 . 7_575
H8B C8 H8C 72.7 . 7_575
H8C C8 H8C 39.6 . 7_575
H8A C8 H8C 109.5 7_575 7_575
H8B C8 H8C 109.5 7_575 7_575
C16 C11 C12 122.5(3) . .
C16 C11 S1 130.8(2) . .
C12 C11 S1 106.7(2) . .
C13 C12 C11 119.6(3) . .
C13 C12 C3 131.2(3) . .
C11 C12 C3 109.2(2) . .
C12 C13 C14 118.9(3) . .
C12 C13 H13 120.5 . .
C14 C13 H13 120.5 . .
C13 C14 C15 120.6(3) . .
C13 C14 H14 119.7 . .
C15 C14 H14 119.7 . .
C16 C15 C14 121.3(3) . .
C16 C15 H15 119.4 . .
C14 C15 H15 119.4 . .
C11 C16 C15 117.1(3) . .
C11 C16 H16 121.4 . .
C15 C16 H16 121.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O11 1.4379(15) 7_575
S1 O11 1.4379(16) .
S1 N2 1.626(2) .
S1 C11 1.771(3) .
N2 C3 1.309(4) .
C3 N4 1.332(4) .
C3 C12 1.485(4) .
N4 N5 1.385(3) .
N4 H4 0.81(3) .
N5 C6 1.286(4) .
C6 C8 1.494(4) .
C6 C7 1.494(4) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C7 H7A 0.9800(15) 7_575
C7 H7B 0.980(19) 7_575
C7 H7C 0.980(18) 7_575
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C8 H8A 0.98(2) 7_575
C8 H8B 0.980(8) 7_575
C8 H8C 0.980(17) 7_575
C11 C16 1.374(4) .
C11 C12 1.392(4) .
C12 C13 1.379(4) .
C13 C14 1.381(4) .
C13 H13 0.9500 .
C14 C15 1.390(5) .
C14 H14 0.9500 .
C15 C16 1.387(5) .
C15 H15 0.9500 .
C16 H16 0.9500 .
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
O11 S1 N2 C3 115.66(8) 7_575
O11 S1 N2 C3 -115.66(8) .
C11 S1 N2 C3 0.000(0) .
S1 N2 C3 N4 180.000(0) .
S1 N2 C3 C12 0.000(0) .
N2 C3 N4 N5 0.000(0) .
C12 C3 N4 N5 180.000(0) .
C3 N4 N5 C6 180.000(0) .
N4 N5 C6 C8 180.000(0) .
N4 N5 C6 C7 0.000(0) .
O11 S1 C11 C16 65.23(8) 7_575
O11 S1 C11 C16 -65.23(8) .
N2 S1 C11 C16 180.000(0) .
O11 S1 C11 C12 -114.77(8) 7_575
O11 S1 C11 C12 114.77(8) .
N2 S1 C11 C12 0.000(0) .
C16 C11 C12 C13 0.000(1) .
S1 C11 C12 C13 180.000(0) .
C16 C11 C12 C3 180.000(0) .
S1 C11 C12 C3 0.000(0) .
N2 C3 C12 C13 180.000(1) .
N4 C3 C12 C13 0.000(1) .
N2 C3 C12 C11 0.000(0) .
N4 C3 C12 C11 180.000(0) .
C11 C12 C13 C14 0.000(1) .
C3 C12 C13 C14 180.000(1) .
C12 C13 C14 C15 0.000(1) .
C13 C14 C15 C16 0.000(1) .
C12 C11 C16 C15 0.000(1) .
S1 C11 C16 C15 180.000(1) .
C14 C15 C16 C11 0.000(1) .
