#------------------------------------------------------------------------------
#$Date: 2025-08-22 14:50:14 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301863 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/33/7203310.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_7203310
loop_
_publ_author_name
'Saha, Binoy K.'
'Nangia, Ashwini'
_publ_section_title
;
 Self-assembled organic tubular host for van der Waals guest inclusion
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              440
_journal_paper_doi               10.1039/b602000n
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C18 H9 Cl3 N6 O3'
_chemical_formula_sum            'C18 H9 Cl3 N6 O3'
_chemical_formula_weight         463.66
_chemical_name_common
2,4,6-tris(2-chloro-3-pyridyloxy)-1,3,5-triazine
_chemical_name_systematic
;
2,4,6-tris(2-chloro-3-pyridyloxy)-1,3,5-triazine
;
_space_group_IT_number           173
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 6c'
_symmetry_space_group_name_H-M   'P 63'
_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                120.00
_cell_formula_units_Z            6
_cell_length_a                   17.2490(9)
_cell_length_b                   17.2490(9)
_cell_length_c                   12.0227(12)
_cell_measurement_reflns_used    9077
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.44
_cell_measurement_theta_min      2.17
_cell_volume                     3097.9(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997) and squeeze'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_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  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            29302
_diffrn_reflns_theta_full        25.48
_diffrn_reflns_theta_max         25.48
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    0.477
_exptl_absorpt_correction_T_max  0.9233
_exptl_absorpt_correction_T_min  0.8861
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1404
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.16(14)
_refine_ls_extinction_coef       0.0005(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3657
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0663
_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)+(0.1058P)²+1.3627P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1769
_refine_ls_wR_factor_ref         0.1910
_reflns_number_gt                2767
_reflns_number_total             3657
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b602000n.txt
_cod_data_source_block           epan5_m
_cod_original_sg_symbol_H-M      P6(3)
_cod_database_code               7203310
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, z+1/2'
'y, -x+y, z+1/2'
'x-y, x, 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
Cl1 Cl 0.5309(3) 0.77046(16) 0.6939(2) 0.1673(14) Uani 1 1 d . . .
Cl2 Cl 0.14747(14) -0.01018(19) 0.69302(16) 0.1277(9) Uani 1 1 d . . .
Cl3 Cl 0.35538(13) 0.82961(13) 0.43813(16) 0.1105(6) Uani 1 1 d . . .
O1 O 0.5052(2) 0.7229(3) 0.9289(4) 0.0767(10) Uani 1 1 d . . .
O2 O 0.1117(2) -0.0613(2) 0.9286(4) 0.0721(9) Uani 1 1 d . . .
O3 O 0.3213(2) 0.8105(2) 0.1999(4) 0.0716(10) Uani 1 1 d . . .
N1 N 0.3903(3) 0.7563(3) 0.9277(4) 0.0644(10) Uani 1 1 d . . .
N2 N 0.6532(4) 0.9226(5) 0.7736(5) 0.0998(18) Uani 1 1 d . . .
N3 N -0.0283(2) -0.0905(2) 0.9305(4) 0.0562(9) Uani 1 1 d . . .
N4 N 0.3107(4) 0.0767(5) 0.7651(5) 0.0974(18) Uani 1 1 d . . .
N5 N 0.4108(3) 0.7481(3) 0.2012(4) 0.0576(9) Uani 1 1 d . . .
N6 N 0.4887(4) 0.9843(4) 0.3754(4) 0.0845(14) Uani 1 1 d . . .
C1 C 0.4179(3) 0.6980(3) 0.9270(4) 0.0591(11) Uani 1 1 d . . .
C2 C 0.5671(4) 0.8145(4) 0.9093(5) 0.0729(14) Uani 1 1 d . . .
C3 C 0.6115(4) 0.8701(4) 0.9938(6) 0.0810(16) Uani 1 1 d . . .
H3 H 0.5977 0.8523 1.0676 0.097 Uiso 1 1 calc R . .
C4 C 0.6804(6) 0.9571(5) 0.9645(8) 0.106(3) Uani 1 1 d . . .
H4 H 0.7136 0.9988 1.0190 0.128 Uiso 1 1 calc R . .
C5 C 0.6965(5) 0.9777(5) 0.8578(9) 0.097(2) Uani 1 1 d . . .
H5 H 0.7418 1.0352 0.8402 0.117 Uiso 1 1 calc R . .
C6 C 0.5898(5) 0.8424(5) 0.8009(5) 0.0870(19) Uani 1 1 d . . .
C7 C 0.0566(4) -0.0262(4) 0.9296(5) 0.0628(12) Uani 1 1 d . . .
C8 C 0.2029(3) 0.0006(4) 0.9049(5) 0.0657(13) Uani 1 1 d . . .
C9 C 0.2661(4) 0.0269(4) 0.9823(6) 0.0811(16) Uani 1 1 d . . .
H9 H 0.2510 0.0093 1.0559 0.097 Uiso 1 1 calc R . .
C10 C 0.3551(5) 0.0810(5) 0.9518(9) 0.111(3) Uani 1 1 d . . .
H10 H 0.4012 0.1000 1.0035 0.134 Uiso 1 1 calc R . .
C11 C 0.3716(5) 0.1046(5) 0.8441(9) 0.104(2) Uani 1 1 d . . .
H11 H 0.4307 0.1437 0.8238 0.125 Uiso 1 1 calc R . .
C12 C 0.2268(4) 0.0262(4) 0.7974(5) 0.0761(15) Uani 1 1 d . . .
C13 C 0.3303(3) 0.7379(3) 0.2017(4) 0.0550(10) Uani 1 1 d . . .
C14 C 0.3972(4) 0.8911(3) 0.2295(5) 0.0641(13) Uani 1 1 d . . .
C15 C 0.4489(6) 0.9531(4) 0.1497(6) 0.091(2) Uani 1 1 d . . .
H15 H 0.4367 0.9419 0.0742 0.110 Uiso 1 1 calc R . .
C16 C 0.5181(5) 1.0306(5) 0.1871(8) 0.103(2) Uani 1 1 d . . .
H16 H 0.5526 1.0754 0.1363 0.124 Uiso 1 1 calc R . .
C17 C 0.5390(5) 1.0451(4) 0.2983(8) 0.093(2) Uani 1 1 d . . .
H17 H 0.5891 1.0982 0.3206 0.111 Uiso 1 1 calc R . .
C18 C 0.4201(4) 0.9086(4) 0.3407(5) 0.0723(14) 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C13 O3 C14 116.0(4) . . ?
C13 N5 C13 111.3(4) . 3_565 ?
N5 C13 N5 128.7(4) . 2_665 ?
N5 C13 O3 119.1(4) . . ?
N5 C13 O3 112.2(4) 2_665 . ?
N6 C18 C14 122.6(6) . . ?
N6 C18 Cl3 118.4(5) . . ?
C14 C18 Cl3 119.0(4) . . ?
C15 C14 C18 120.0(6) . . ?
C15 C14 O3 121.0(6) . . ?
C18 C14 O3 119.0(5) . . ?
C18 N6 C17 117.8(6) . . ?
C16 C15 C14 116.4(7) . . ?
C16 C15 H15 121.8 . . ?
C14 C15 H15 121.8 . . ?
C15 C16 C17 121.8(7) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C7 N3 C7 111.2(5) . 3 ?
C7 O2 C8 115.3(4) . . ?
C9 C8 C12 119.3(5) . . ?
C9 C8 O2 121.8(5) . . ?
C12 C8 O2 118.5(5) . . ?
N3 C7 N3 128.8(5) . 2 ?
N3 C7 O2 110.8(4) . . ?
N3 C7 O2 120.4(5) 2 . ?
C11 C10 C9 117.0(7) . . ?
C11 C10 H10 121.5 . . ?
C9 C10 H10 121.5 . . ?
N4 C12 C8 123.2(6) . . ?
N4 C12 Cl2 115.8(5) . . ?
C8 C12 Cl2 121.0(4) . . ?
C11 N4 C12 116.2(6) . . ?
C8 C9 C10 119.1(7) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
N4 C11 C10 125.0(7) . . ?
N4 C11 H11 117.5 . . ?
C10 C11 H11 117.5 . . ?
C1 O1 C2 116.9(4) . . ?
C1 N1 C1 114.1(5) . 2_665 ?
N1 C1 N1 125.9(5) . 3_565 ?
N1 C1 O1 122.2(5) . . ?
N1 C1 O1 111.8(4) 3_565 . ?
C3 C2 C6 120.4(6) . . ?
C3 C2 O1 120.9(5) . . ?
C6 C2 O1 118.1(6) . . ?
C5 C4 C3 118.6(7) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 N2 125.3(7) . . ?
C4 C5 H5 117.4 . . ?
N2 C5 H5 117.4 . . ?
N2 C6 C2 123.3(7) . . ?
N2 C6 Cl1 117.1(5) . . ?
C2 C6 Cl1 119.6(5) . . ?
C2 C3 C4 116.4(7) . . ?
C2 C3 H3 121.8 . . ?
C4 C3 H3 121.8 . . ?
C6 N2 C5 115.9(6) . . ?
N6 C17 C16 121.4(6) . . ?
N6 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
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
Cl3 C18 1.719(6) . ?
O3 C13 1.337(6) . ?
O3 C14 1.398(7) . ?
N5 C13 1.309(6) . ?
N5 C13 1.325(6) 3_565 ?
C13 N5 1.325(6) 2_665 ?
C18 N6 1.317(8) . ?
C18 C14 1.384(9) . ?
C14 C15 1.380(8) . ?
N6 C17 1.342(9) . ?
C15 C16 1.349(11) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(11) . ?
C16 H16 0.9300 . ?
Cl2 C12 1.727(6) . ?
N3 C7 1.324(7) . ?
N3 C7 1.334(7) 3 ?
O2 C7 1.357(6) . ?
O2 C8 1.419(6) . ?
C8 C9 1.329(8) . ?
C8 C12 1.361(9) . ?
C7 N3 1.334(7) 2 ?
C10 C11 1.345(12) . ?
C10 C9 1.389(11) . ?
C10 H10 0.9300 . ?
C12 N4 1.321(8) . ?
N4 C11 1.315(11) . ?
C9 H9 0.9300 . ?
C11 H11 0.9300 . ?
Cl1 C6 1.722(7) . ?
O1 C1 1.345(6) . ?
O1 C2 1.417(7) . ?
N1 C1 1.310(6) . ?
N1 C1 1.325(6) 2_665 ?
C1 N1 1.325(6) 3_565 ?
C2 C3 1.343(9) . ?
C2 C6 1.376(9) . ?
C4 C5 1.322(11) . ?
C4 C3 1.416(11) . ?
C4 H4 0.9300 . ?
C5 N2 1.333(11) . ?
C5 H5 0.9300 . ?
C6 N2 1.306(9) . ?
C3 H3 0.9300 . ?
C17 H17 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139195082
