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#$Date: 2022-11-29 10:55:13 +0200 (Tue, 29 Nov 2022) $
#$Revision: 279623 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/62/8106293.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_8106293
loop_
_publ_author_name
'Song, Xiao'
'Tang, Zhishu'
'Zuo, Zhenyu'
'Duan, Jinao'
_publ_section_title
;
 The crystal structure of 2-(tert-butyl)-4-chloro-6-phenyl-1,3,5-triazine,
 C13H14Cl1N3
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              779
_journal_page_last               781
_journal_paper_doi               10.1515/ncrs-2017-0386
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C13 H14 Cl N3'
_chemical_formula_sum            'C13 H14 Cl N3'
_chemical_formula_weight         247.72
_space_group_crystal_system      orthorhombic
_space_group_IT_number           28
_space_group_name_Hall           'P 2 -2a'
_space_group_name_H-M_alt        'P m a 2'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7623(2)
_cell_length_b                   21.1431(6)
_cell_length_c                   8.8708(2)
_cell_measurement_reflns_used    6997
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      68.207
_cell_measurement_theta_min      2.090
_cell_volume                     1268.31(6)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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 CCD'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14980
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.205
_diffrn_reflns_theta_min         2.090
_exptl_absorpt_coefficient_mu    2.503
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       Block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.50(2)
_refine_ls_extinction_coef       0.0029(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2537
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0362
_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)+(0.0580P)²+0.0590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0969
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2324
_reflns_number_total             2537
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0386_suppl.cif
_cod_data_source_block           1
_cod_database_code               8106293
_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   0.705
_shelx_estimated_absorpt_t_max   0.788
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y, z'
'x+1/2, -y, 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_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
Cl1 Cl -0.250000 0.71123(5) 1.41697(10) 0.0471(3) Uani 1 2 d S T P . .
N1 N -0.250000 0.66798(16) 1.1436(4) 0.0369(8) Uani 1 2 d S T P . .
N2 N -0.250000 0.55879(16) 1.0871(4) 0.0342(8) Uani 1 2 d S T P . .
N3 N -0.250000 0.59247(17) 1.3425(4) 0.0337(8) Uani 1 2 d S T P . .
C1 C -0.250000 0.65043(18) 1.2865(5) 0.0330(8) Uani 1 2 d S T P . .
C2 C -0.250000 0.61896(19) 1.0459(5) 0.0355(9) Uani 1 2 d DS T P . .
C3 C -0.250000 0.54733(18) 1.2360(4) 0.0307(8) Uani 1 2 d S T P . .
C4 C -0.250000 0.48098(18) 1.2860(5) 0.0322(8) Uani 1 2 d S T P . .
C5 C -0.250000 0.4322(2) 1.1796(5) 0.0392(10) Uani 1 2 d S T P . .
H5 H -0.250000 0.441954 1.075116 0.047 Uiso 1 2 calc R U P . .
C6 C -0.250000 0.3698(2) 1.2257(6) 0.0463(11) Uani 1 2 d S T P . .
H6 H -0.250000 0.336897 1.152811 0.056 Uiso 1 2 calc R U P . .
C7 C -0.250000 0.3551(2) 1.3770(6) 0.0468(12) Uani 1 2 d S T P . .
H7 H -0.250000 0.312133 1.408149 0.056 Uiso 1 2 calc R U P . .
C8 C -0.250000 0.4029(2) 1.4836(6) 0.0490(12) Uani 1 2 d S T P . .
H8 H -0.250000 0.392480 1.587801 0.059 Uiso 1 2 calc R U P . .
C9 C -0.250000 0.4659(2) 1.4393(5) 0.0402(10) Uani 1 2 d S T P . .
H9 H -0.250000 0.498505 1.512914 0.048 Uiso 1 2 calc R U P . .
C10 C -0.250000 0.6356(2) 0.8796(5) 0.0410(10) Uani 1 2 d DS T P . .
C11 C -0.4336(6) 0.6765(2) 0.8475(4) 0.0662(10) Uani 1 1 d D . . . .
H11A H -0.429089 0.714704 0.909757 0.099 Uiso 1 1 calc R U . . .
H11B H -0.553170 0.652291 0.871417 0.099 Uiso 1 1 calc R U . . .
H11C H -0.435345 0.688360 0.740698 0.099 Uiso 1 1 calc R U . . .
C12 C -0.250000 0.5773(3) 0.7819(6) 0.084(2) Uani 1 2 d DS T P . .
Cl2 Cl -0.250000 0.20354(5) 1.14771(11) 0.0488(4) Uani 1 2 d S T P . .
N4 N -0.250000 0.08493(16) 1.0723(4) 0.0332(8) Uani 1 2 d S T P . .
N5 N -0.250000 0.05119(16) 0.8158(4) 0.0330(7) Uani 1 2 d S T P . .
N6 N -0.250000 0.16102(16) 0.8735(4) 0.0354(7) Uani 1 2 d S T P . .
C13 C -0.250000 0.14331(19) 1.0165(4) 0.0330(8) Uani 1 2 d S T P . .
C14 C -0.250000 0.11263(18) 0.7758(5) 0.0329(8) Uani 1 2 d DS T P . .
C15 C -0.250000 0.04038(18) 0.9650(4) 0.0307(8) Uani 1 2 d S T P . .
C16 C -0.250000 -0.02651(18) 1.0143(5) 0.0313(8) Uani 1 2 d S T P . .
C17 C -0.250000 -0.07472(19) 0.9077(5) 0.0372(9) Uani 1 2 d S T P . .
H17 H -0.250000 -0.064532 0.803370 0.045 Uiso 1 2 calc R U P . .
C18 C -0.250000 -0.1374(2) 0.9523(6) 0.0432(10) Uani 1 2 d S T P . .
H18 H -0.250000 -0.170019 0.878681 0.052 Uiso 1 2 calc R U P . .
C19 C -0.250000 -0.1527(2) 1.1049(6) 0.0447(11) Uani 1 2 d S T P . .
H19 H -0.250000 -0.195758 1.135843 0.054 Uiso 1 2 calc R U P . .
C20 C -0.250000 -0.1054(2) 1.2097(5) 0.0465(11) Uani 1 2 d S T P . .
H20 H -0.250000 -0.115859 1.313849 0.056 Uiso 1 2 calc R U P . .
C21 C -0.250000 -0.0420(2) 1.1667(5) 0.0394(9) Uani 1 2 d S T P . .
H21 H -0.250000 -0.009616 1.240954 0.047 Uiso 1 2 calc R U P . .
C22 C -0.250000 0.12908(19) 0.6090(5) 0.0368(9) Uani 1 2 d DS T P . .
C23 C -0.4284(9) 0.1696(4) 0.5768(5) 0.115(3) Uani 1 1 d D . . . .
H23A H -0.548881 0.144632 0.591296 0.172 Uiso 1 1 calc R U . . .
H23B H -0.422628 0.184785 0.472452 0.172 Uiso 1 1 calc R U . . .
H23C H -0.429579 0.205900 0.645614 0.172 Uiso 1 1 calc R U . . .
C24 C -0.250000 0.0713(4) 0.5126(8) 0.144(6) Uani 1 2 d DS T P . .
H12A H -0.368(5) 0.5518(16) 0.805(3) 0.215 Uiso 1 1 d D U . A -1
H12B H -0.253(5) 0.5897(9) 0.6756(13) 0.215 Uiso 0.5 1 d D U P B -1
H24A H -0.367(5) 0.0460(16) 0.535(3) 0.215 Uiso 1 1 d D U . C -1
H24B H -0.250(5) 0.0840(9) 0.4066(14) 0.215 Uiso 0.5 1 d D U P D -1
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'
Cl Cl 0.3639 0.7018 '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'
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 N1 C2 113.6(3) . .
C2 N2 C3 116.4(4) . .
C1 N3 C3 113.2(4) . .
N1 C1 N3 128.4(4) . .
N1 C1 Cl1 115.7(3) . .
N3 C1 Cl1 115.9(3) . .
N2 C2 N1 124.0(4) . .
N2 C2 C10 119.5(4) . .
N1 C2 C10 116.5(3) . .
N2 C3 N3 124.3(4) . .
N2 C3 C4 118.0(4) . .
N3 C3 C4 117.7(4) . .
C9 C4 C5 119.2(4) . .
C9 C4 C3 120.8(4) . .
C5 C4 C3 120.0(4) . .
C6 C5 C4 120.3(4) . .
C7 C6 C5 120.3(4) . .
C6 C7 C8 120.1(4) . .
C7 C8 C9 120.4(4) . .
C8 C9 C4 119.7(4) . .
C12 C10 C2 111.7(4) . .
C12 C10 C11 110.6(3) . .
C2 C10 C11 108.1(2) . .
C12 C10 C11 110.6(3) . 3_455
C2 C10 C11 108.1(2) . 3_455
C11 C10 C11 107.6(4) . 3_455
C13 N4 C15 112.8(3) . .
C15 N5 C14 115.1(4) . .
C13 N6 C14 113.8(3) . .
N6 C13 N4 128.3(4) . .
N6 C13 Cl2 116.0(3) . .
N4 C13 Cl2 115.7(3) . .
N6 C14 N5 124.5(4) . .
N6 C14 C22 117.0(3) . .
N5 C14 C22 118.5(3) . .
N4 C15 N5 125.5(4) . .
N4 C15 C16 117.5(3) . .
N5 C15 C16 117.0(4) . .
C17 C16 C21 119.2(4) . .
C17 C16 C15 120.0(4) . .
C21 C16 C15 120.8(4) . .
C18 C17 C16 120.5(4) . .
C17 C18 C19 120.1(4) . .
C20 C19 C18 119.4(4) . .
C19 C20 C21 121.2(4) . .
C16 C21 C20 119.5(4) . .
C24 C22 C23 110.9(4) . 3_455
C24 C22 C23 110.9(4) . .
C23 C22 C23 106.3(7) 3_455 .
C24 C22 C14 111.8(4) . .
C23 C22 C14 108.4(3) 3_455 .
C23 C22 C14 108.4(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C1 1.730(4) .
N1 C1 1.320(5) .
N1 C2 1.351(5) .
N2 C2 1.324(5) .
N2 C3 1.343(5) .
N3 C1 1.322(6) .
N3 C3 1.343(5) .
C2 C10 1.516(6) .
C3 C4 1.471(5) .
C4 C9 1.397(6) .
C4 C5 1.399(6) .
C5 C6 1.380(6) .
C6 C7 1.377(8) .
C7 C8 1.383(7) .
C8 C9 1.389(7) .
C10 C12 1.507(7) .
C10 C11 1.538(5) .
C10 C11 1.538(5) 3_455
Cl2 C13 1.725(4) .
N4 C13 1.330(5) .
N4 C15 1.339(5) .
N5 C15 1.343(5) .
N5 C14 1.347(5) .
N6 C13 1.323(5) .
N6 C14 1.341(5) .
C14 C22 1.520(5) .
C15 C16 1.480(5) .
C16 C17 1.390(6) .
C16 C21 1.392(6) .
C17 C18 1.383(6) .
C18 C19 1.392(7) .
C19 C20 1.367(7) .
C20 C21 1.393(6) .
C22 C24 1.491(8) .
C22 C23 1.507(5) 3_455
C22 C23 1.507(5) .
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
C2 N1 C1 N3 0.000(3) . . . .
C2 N1 C1 Cl1 180.000(2) . . . .
C3 N3 C1 N1 0.000(3) . . . .
C3 N3 C1 Cl1 180.000(2) . . . .
C3 N2 C2 N1 0.000(3) . . . .
C3 N2 C2 C10 180.000(2) . . . .
C1 N1 C2 N2 0.000(3) . . . .
C1 N1 C2 C10 180.000(2) . . . .
C2 N2 C3 N3 0.000(3) . . . .
C2 N2 C3 C4 180.000(2) . . . .
C1 N3 C3 N2 0.000(3) . . . .
C1 N3 C3 C4 180.000(2) . . . .
N2 C3 C4 C9 180.000(3) . . . .
N3 C3 C4 C9 0.000(3) . . . .
N2 C3 C4 C5 0.000(3) . . . .
N3 C3 C4 C5 180.000(3) . . . .
C9 C4 C5 C6 0.000(3) . . . .
C3 C4 C5 C6 180.000(3) . . . .
C4 C5 C6 C7 0.000(4) . . . .
C5 C6 C7 C8 0.000(4) . . . .
C6 C7 C8 C9 0.000(4) . . . .
C7 C8 C9 C4 0.000(3) . . . .
C5 C4 C9 C8 0.000(3) . . . .
C3 C4 C9 C8 180.000(3) . . . .
N2 C2 C10 C12 0.000(3) . . . .
N1 C2 C10 C12 180.000(3) . . . .
N2 C2 C10 C11 121.9(3) . . . .
N1 C2 C10 C11 -58.1(3) . . . .
N2 C2 C10 C11 -121.9(3) . . . 3_455
N1 C2 C10 C11 58.1(3) . . . 3_455
C14 N6 C13 N4 0.000(2) . . . .
C14 N6 C13 Cl2 180.000(1) . . . .
C15 N4 C13 N6 0.000(2) . . . .
C15 N4 C13 Cl2 180.000(1) . . . .
C13 N6 C14 N5 0.000(1) . . . .
C13 N6 C14 C22 180.000(1) . . . .
C15 N5 C14 N6 0.000(1) . . . .
C15 N5 C14 C22 180.000(1) . . . .
C13 N4 C15 N5 0.000(1) . . . .
C13 N4 C15 C16 180.000(1) . . . .
C14 N5 C15 N4 0.000(1) . . . .
C14 N5 C15 C16 180.000(1) . . . .
N4 C15 C16 C17 180.000(1) . . . .
N5 C15 C16 C17 0.000(1) . . . .
N4 C15 C16 C21 0.000(1) . . . .
N5 C15 C16 C21 180.000(1) . . . .
C21 C16 C17 C18 0.000(1) . . . .
C15 C16 C17 C18 180.000(1) . . . .
C16 C17 C18 C19 0.000(1) . . . .
C17 C18 C19 C20 0.000(1) . . . .
C18 C19 C20 C21 0.000(1) . . . .
C17 C16 C21 C20 0.000(1) . . . .
C15 C16 C21 C20 180.000(1) . . . .
C19 C20 C21 C16 0.000(1) . . . .
N6 C14 C22 C24 180.000(1) . . . .
N5 C14 C22 C24 0.000(1) . . . .
N6 C14 C22 C23 57.5(4) . . . 3_455
N5 C14 C22 C23 -122.5(4) . . . 3_455
N6 C14 C22 C23 -57.5(4) . . . .
N5 C14 C22 C23 122.5(4) . . . .
