#------------------------------------------------------------------------------
#$Date: 2022-04-09 03:46:45 +0300 (Sat, 09 Apr 2022) $
#$Revision: 274444 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158633.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_7158633
loop_
_publ_author_name
'Liao, Hui'
'Huang, Zesheng'
'Zhu, Qiuhua'
_publ_section_title
;
 A simple Iodine-DMSO-promoted multicomponent reaction for the synthesis
 of 2,4-disubstituted dihydrotriazole-3-ones
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00352J
_journal_year                    2022
_chemical_formula_moiety         'C14 H11 N3 O'
_chemical_formula_sum            'C14 H11 N3 O'
_chemical_formula_weight         237.26
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-02-16 deposited with the CCDC.	2022-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.628(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7128(11)
_cell_length_b                   7.4784(7)
_cell_length_c                   11.7095(9)
_cell_measurement_reflns_used    1056
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.8020
_cell_measurement_theta_min      3.8160
_cell_volume                     1192.78(17)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1281
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00 -17.00   1.00    1.00    --  -33.50 -57.00  90.00   28
  2  ω    -28.00  52.00   1.00    1.00    --   36.12 -37.00   0.00   80
  3  ω     54.00  81.00   1.00    1.00    --   36.12  57.00-120.00   27
  4  ω     19.00  46.00   1.00    1.00    --   36.12  57.00-120.00   27
  5  ω     60.00 107.00   1.00    1.00    --   36.12  19.00 120.00   47
  6  ω     -4.00  75.00   1.00    1.00    --   36.12 -99.00 -30.00   79
  7  ω      9.00  61.00   1.00    1.00    --   36.12  77.00 150.00   52
  8  ω    123.00 150.00   1.00    1.00    --  108.00 178.00 -90.00   27
  9  ω     60.00  95.00   1.00    1.00    --  108.00 178.00 -90.00   35
 10  ω     93.00 176.00   1.00    1.00    --  108.00  45.00-150.00   83
 11  ω     39.00  67.00   1.00    1.00    --  108.00 -94.00  60.00   28
 12  ω     84.00 109.00   1.00    1.00    --  108.00 -94.00  60.00   25
 13  ω     41.00 129.00   1.00    1.00    --  108.00-141.00 -18.00   88
 14  ω     92.00 131.00   1.00    1.00    --  108.00  61.00-180.00   39
 15  ω     81.00 174.00   1.00    1.00    --  108.00  77.00-120.00   93
 16  ω     40.00 135.00   1.00    1.00    --  108.00 -77.00 120.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0197994000
_diffrn_orient_matrix_UB_12      0.2025954000
_diffrn_orient_matrix_UB_13      0.0080155000
_diffrn_orient_matrix_UB_21      -0.0987437000
_diffrn_orient_matrix_UB_22      0.0359821000
_diffrn_orient_matrix_UB_23      -0.0732440000
_diffrn_orient_matrix_UB_31      -0.0514803000
_diffrn_orient_matrix_UB_32      0.0089769000
_diffrn_orient_matrix_UB_33      0.1100830000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4303
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.384
_diffrn_reflns_theta_min         3.245
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0106(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0458
_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)+(0.0408P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1213
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1447
_reflns_number_total             2258
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00352j2.cif
_cod_data_source_block           exp_10674
_cod_database_code               7158633
_shelx_shelxl_version_number     2018/3
_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.
;
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.806
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
O1 O 0.40615(10) 0.3012(2) 0.41625(11) 0.0682(5) Uani 1 1 d . . . . .
N1 N 0.43704(12) 0.3917(2) 0.23229(13) 0.0515(4) Uani 1 1 d . . . . .
N2 N 0.28559(12) 0.3810(2) 0.26680(13) 0.0543(5) Uani 1 1 d . . . . .
N3 N 0.28487(13) 0.4396(3) 0.15424(14) 0.0641(5) Uani 1 1 d . . . . .
C1 C 0.37932(15) 0.3508(3) 0.31858(16) 0.0518(5) Uani 1 1 d . . . . .
C2 C 0.54143(15) 0.3821(3) 0.23882(17) 0.0502(5) Uani 1 1 d . . . . .
C3 C 0.19566(14) 0.3666(3) 0.31427(17) 0.0538(5) Uani 1 1 d . . . . .
C4 C 0.58346(15) 0.3164(3) 0.14552(17) 0.0568(6) Uani 1 1 d . . . . .
H4 H 0.544039 0.273994 0.081286 0.068 Uiso 1 1 calc R . . . .
C5 C 0.37561(16) 0.4429(3) 0.13778(17) 0.0628(6) Uani 1 1 d . . . . .
H5 H 0.397405 0.476617 0.068604 0.075 Uiso 1 1 calc R . . . .
C6 C 0.18703(16) 0.2575(3) 0.40685(17) 0.0656(6) Uani 1 1 d . . . . .
H6 H 0.240601 0.191673 0.439717 0.079 Uiso 1 1 calc R . . . .
C7 C 0.59895(16) 0.4441(3) 0.33540(18) 0.0613(6) Uani 1 1 d . . . . .
H7 H 0.570387 0.487414 0.398164 0.074 Uiso 1 1 calc R . . . .
C8 C 0.68391(16) 0.3144(3) 0.1484(2) 0.0683(7) Uani 1 1 d . . . . .
H8 H 0.712580 0.270763 0.085831 0.082 Uiso 1 1 calc R . . . .
C9 C 0.69965(17) 0.4403(3) 0.3367(2) 0.0725(7) Uani 1 1 d . . . . .
H9 H 0.739341 0.481242 0.401132 0.087 Uiso 1 1 calc R . . . .
C10 C 0.11540(16) 0.4645(3) 0.2659(2) 0.0682(7) Uani 1 1 d . . . . .
H10 H 0.121259 0.539056 0.203488 0.082 Uiso 1 1 calc R . . . .
C11 C 0.09728(18) 0.2465(4) 0.45099(19) 0.0805(8) Uani 1 1 d . . . . .
H11 H 0.091152 0.173511 0.514075 0.097 Uiso 1 1 calc R . . . .
C12 C 0.74225(17) 0.3767(3) 0.2436(2) 0.0759(7) Uani 1 1 d . . . . .
H12 H 0.810214 0.375972 0.245173 0.091 Uiso 1 1 calc R . . . .
C13 C 0.01778(18) 0.3421(4) 0.4025(2) 0.0821(8) Uani 1 1 d . . . . .
H13 H -0.042155 0.332924 0.431939 0.098 Uiso 1 1 calc R . . . .
C14 C 0.02705(18) 0.4510(4) 0.3104(2) 0.0811(8) Uani 1 1 d . . . . .
H14 H -0.026744 0.516403 0.277732 0.097 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_publ_flag
C1 N1 C2 127.09(16) . . ?
C5 N1 C1 107.54(16) . . ?
C5 N1 C2 125.37(17) . . ?
N3 N2 C3 119.10(17) . . ?
C1 N2 N3 111.99(16) . . ?
C1 N2 C3 128.86(17) . . ?
C5 N3 N2 104.38(17) . . ?
O1 C1 N1 127.94(19) . . ?
O1 C1 N2 129.03(19) . . ?
N2 C1 N1 103.03(16) . . ?
C4 C2 N1 118.86(18) . . ?
C7 C2 N1 120.09(18) . . ?
C7 C2 C4 121.0(2) . . ?
C6 C3 N2 121.0(2) . . ?
C6 C3 C10 120.0(2) . . ?
C10 C3 N2 119.1(2) . . ?
C2 C4 H4 120.3 . . ?
C8 C4 C2 119.5(2) . . ?
C8 C4 H4 120.3 . . ?
N1 C5 H5 123.5 . . ?
N3 C5 N1 113.05(18) . . ?
N3 C5 H5 123.5 . . ?
C3 C6 H6 120.4 . . ?
C3 C6 C11 119.3(2) . . ?
C11 C6 H6 120.4 . . ?
C2 C7 H7 120.7 . . ?
C9 C7 C2 118.5(2) . . ?
C9 C7 H7 120.7 . . ?
C4 C8 H8 119.9 . . ?
C4 C8 C12 120.3(2) . . ?
C12 C8 H8 119.9 . . ?
C7 C9 H9 119.6 . . ?
C12 C9 C7 120.9(2) . . ?
C12 C9 H9 119.6 . . ?
C3 C10 H10 120.1 . . ?
C14 C10 C3 119.9(2) . . ?
C14 C10 H10 120.1 . . ?
C6 C11 H11 119.7 . . ?
C13 C11 C6 120.7(2) . . ?
C13 C11 H11 119.7 . . ?
C8 C12 C9 119.8(2) . . ?
C8 C12 H12 120.1 . . ?
C9 C12 H12 120.1 . . ?
C11 C13 H13 120.2 . . ?
C14 C13 C11 119.7(2) . . ?
C14 C13 H13 120.2 . . ?
C10 C14 H14 119.7 . . ?
C13 C14 C10 120.5(2) . . ?
C13 C14 H14 119.7 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.218(2) . ?
N1 C1 1.388(2) . ?
N1 C2 1.427(2) . ?
N1 C5 1.366(2) . ?
N2 N3 1.388(2) . ?
N2 C1 1.375(2) . ?
N2 C3 1.414(2) . ?
N3 C5 1.281(2) . ?
C2 C4 1.383(3) . ?
C2 C7 1.382(3) . ?
C3 C6 1.373(3) . ?
C3 C10 1.387(3) . ?
C4 H4 0.9300 . ?
C4 C8 1.374(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C6 C11 1.391(3) . ?
C7 H7 0.9300 . ?
C7 C9 1.380(3) . ?
C8 H8 0.9300 . ?
C8 C12 1.376(3) . ?
C9 H9 0.9300 . ?
C9 C12 1.379(3) . ?
C10 H10 0.9300 . ?
C10 C14 1.377(3) . ?
C11 H11 0.9300 . ?
C11 C13 1.371(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.368(3) . ?
C14 H14 0.9300 . ?
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
_geom_torsion_publ_flag
N1 C2 C4 C8 176.88(18) . . . . ?
N1 C2 C7 C9 -177.06(19) . . . . ?
N2 N3 C5 N1 -0.5(3) . . . . ?
N2 C3 C6 C11 -179.85(19) . . . . ?
N2 C3 C10 C14 179.5(2) . . . . ?
N3 N2 C1 O1 179.1(2) . . . . ?
N3 N2 C1 N1 -0.6(2) . . . . ?
N3 N2 C3 C6 158.20(19) . . . . ?
N3 N2 C3 C10 -21.7(3) . . . . ?
C1 N1 C2 C4 139.4(2) . . . . ?
C1 N1 C2 C7 -43.0(3) . . . . ?
C1 N1 C5 N3 0.2(3) . . . . ?
C1 N2 N3 C5 0.7(2) . . . . ?
C1 N2 C3 C6 -24.6(3) . . . . ?
C1 N2 C3 C10 155.5(2) . . . . ?
C2 N1 C1 O1 1.0(4) . . . . ?
C2 N1 C1 N2 -179.38(18) . . . . ?
C2 N1 C5 N3 179.83(19) . . . . ?
C2 C4 C8 C12 0.2(3) . . . . ?
C2 C7 C9 C12 0.2(4) . . . . ?
C3 N2 N3 C5 178.35(19) . . . . ?
C3 N2 C1 O1 1.7(4) . . . . ?
C3 N2 C1 N1 -177.95(19) . . . . ?
C3 C6 C11 C13 0.5(4) . . . . ?
C3 C10 C14 C13 0.2(4) . . . . ?
C4 C2 C7 C9 0.4(3) . . . . ?
C4 C8 C12 C9 0.4(4) . . . . ?
C5 N1 C1 O1 -179.4(2) . . . . ?
C5 N1 C1 N2 0.3(2) . . . . ?
C5 N1 C2 C4 -40.2(3) . . . . ?
C5 N1 C2 C7 137.4(2) . . . . ?
C6 C3 C10 C14 -0.4(3) . . . . ?
C6 C11 C13 C14 -0.7(4) . . . . ?
C7 C2 C4 C8 -0.6(3) . . . . ?
C7 C9 C12 C8 -0.6(4) . . . . ?
C10 C3 C6 C11 0.1(3) . . . . ?
C11 C13 C14 C10 0.4(4) . . . . ?
