#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/49/4504959.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_4504959
loop_
_publ_author_name
'Saha, Binoy K.'
'Jetti, Ram K. R.'
'Reddy, L. Sreenivas'
'Aitipamula, Srinivasulu'
'Nangia, Ashwini'
_publ_section_title
;
 Halogen Trimer-Mediated Hexagonal Host Framework of
 2,4,6-Tris(4-halophenoxy)-1,3,5-triazine. Supramolecular Isomerism from
 Hexagonal Channel (X = Cl, Br) to Cage Structure (X = I)
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              887
_journal_paper_doi               10.1021/cg049691r
_journal_volume                  5
_journal_year                    2005
_chemical_formula_moiety         '2(C21 H12 N3 O3 I3), C11 H10'
_chemical_formula_sum            'C53 H34 I6 N6 O6'
_chemical_formula_weight         1612.26
_chemical_name_common
'2,4,6-tris(4-iodophenoxy)-1,3,5-triazine, 1-methylnapthalene'
_chemical_name_systematic
; 
  2,4,6-tris(4-iodophenoxy)-1,3,5-triazine, 1-methylnapthalene 
;
_space_group_IT_number           148
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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            3
_cell_length_a                   15.5830(6)
_cell_length_b                   15.5830(6)
_cell_length_c                   18.3563(14)
_cell_measurement_reflns_used    6513
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.61
_cell_volume                     3860.3(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)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_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  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8891
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    3.678
_exptl_absorpt_correction_T_max  0.46
_exptl_absorpt_correction_T_min  0.37
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Bruker Nonius area detector scaling and absorption correction -V2.10'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.081
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2280
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.734
_refine_diff_density_rms         0.127
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2073
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0210
_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)+(0.0285P)²+8.7098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0546
_refine_ls_wR_factor_ref         0.0553
_reflns_number_gt                2000
_reflns_number_total             2073
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg049691rsi20040907_112754.cif
_cod_data_source_block           an17_m
_cod_original_sg_symbol_H-M      R-3
_cod_original_formula_sum        'C53  H34  I6  N6  O6'
_cod_database_code               4504959
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
I1 I 0.897157(11) 1.058627(11) 0.205339(8) 0.02048(7) Uani 1 1 d .
O1 O 0.44154(12) 0.85972(12) 0.25741(8) 0.0174(3) Uani 1 1 d .
C4 C 0.54494(16) 0.90490(16) 0.24738(11) 0.0156(4) Uani 1 1 d .
N1 N 0.29115(14) 0.72593(14) 0.25855(9) 0.0155(4) Uani 1 1 d .
C6 C 0.38894(17) 0.76081(16) 0.25852(10) 0.0147(4) Uani 1 1 d .
C3 C 0.58177(18) 0.94515(18) 0.17983(12) 0.0197(5) Uani 1 1 d .
H3 H 0.5385 0.9415 0.1420 0.024 Uiso 1 1 calc R
C1 C 0.74496(17) 0.99600(16) 0.22448(12) 0.0174(4) Uani 1 1 d .
C5 C 0.60551(18) 0.91051(18) 0.30440(12) 0.0205(5) Uani 1 1 d .
H5 H 0.5781 0.8830 0.3506 0.025 Uiso 1 1 calc R
C2 C 0.68319(18) 0.99111(18) 0.16823(12) 0.0204(5) Uani 1 1 d .
H2 H 0.7102 1.0191 0.1220 0.024 Uiso 1 1 calc R
C7 C 0.70705(18) 0.95700(18) 0.29290(12) 0.0207(5) Uani 1 1 d .
H7 H 0.7502 0.9621 0.3313 0.025 Uiso 1 1 calc R
C8 C 0.6518(4) 0.1687(3) 0.33014(19) 0.0422(9) Uani 0.85 1 d P
C11 C 0.7123(5) 0.2737(5) 0.3339(3) 0.0340(13) Uani 0.50 1 d P
C12 C 0.6667 0.3333 0.3333 0.0255(13) Uani 1 6 d S
C13 C 0.7572(8) 0.2148(8) 0.3352(5) 0.037(2) Uani 0.32 1 d 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'
I I -0.4742 1.8119 '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
C6 O1 C4 117.81(18) . .
C3 C4 C5 122.4(2) . .
C3 C4 O1 117.14(19) . .
C5 C4 O1 120.39(19) . .
C6 N1 C6 112.7(2) 2_665 .
N1 C6 O1 120.0(2) 3_565 .
N1 C6 N1 127.3(2) 3_565 .
O1 C6 N1 112.7(2) . .
C4 C3 C2 118.7(2) . .
C2 C1 C7 121.1(2) . .
C2 C1 I1 119.58(16) . .
C7 C1 I1 119.30(17) . .
C4 C5 C7 118.8(2) . .
C3 C2 C1 119.6(2) . .
C5 C7 C1 119.3(2) . .
C13 C8 C11 59.9(5) 17 17
C13 C8 C11 120.3(5) 17 .
C11 C8 C11 60.4(5) 17 .
C13 C8 C13 175.3(3) 17 .
C11 C8 C13 119.3(5) 17 .
C11 C8 C13 59.0(5) . .
C13 C11 C8 59.8(5) . 18_545
C13 C11 C8 60.7(6) . .
C8 C11 C8 120.5(5) 18_545 .
C13 C11 C12 179.4(5) . .
C8 C11 C12 120.2(5) 18_545 .
C8 C11 C12 119.2(5) . .
C13 C11 C11 120.1(8) . 18_545
C8 C11 C11 60.3(5) 18_545 18_545
C8 C11 C11 176.3(7) . 18_545
C12 C11 C11 59.998(3) . 18_545
C13 C11 C11 119.9(8) . 17
C8 C11 C11 178.9(6) 18_545 17
C8 C11 C11 59.3(5) . 17
C12 C11 C11 60.000(4) . 17
C11 C11 C11 119.98(2) 18_545 17
C11 C12 C11 60.006(6) 16_655 2_655
C11 C12 C11 119.999(7) 16_655 18_545
C11 C12 C11 60.009(6) 2_655 18_545
C11 C12 C11 179.997(2) 16_655 .
C11 C12 C11 119.996(8) 2_655 .
C11 C12 C11 60.003(6) 18_545 .
C11 C12 C11 60.005(7) 16_655 3_665
C11 C12 C11 119.994(6) 2_655 3_665
C11 C12 C11 180.0 18_545 3_665
C11 C12 C11 119.994(7) . 3_665
C11 C12 C11 119.995(7) 16_655 17
C11 C12 C11 179.995(1) 2_655 17
C11 C12 C11 119.990(6) 18_545 17
C11 C12 C11 60.004(7) . 17
C11 C12 C11 60.006(7) 3_665 17
C8 C13 C11 60.3(5) 18_545 .
C8 C13 C8 120.5(7) 18_545 .
C11 C13 C8 60.3(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C1 2.094(2) .
O1 C6 1.336(3) .
O1 C4 1.411(3) .
C4 C3 1.379(3) .
C4 C5 1.383(3) .
N1 C6 1.321(3) 2_665
N1 C6 1.338(3) .
C6 N1 1.321(3) 3_565
C3 C2 1.387(3) .
C1 C2 1.387(3) .
C1 C7 1.392(3) .
C5 C7 1.388(3) .
C8 C13 1.403(12) 17
C8 C11 1.409(8) 17
C8 C11 1.424(8) .
C8 C13 1.430(11) .
C11 C13 1.405(11) .
C11 C8 1.409(8) 18_545
C11 C12 1.426(6) .
C11 C11 1.426(6) 18_545
C11 C11 1.426(6) 17
C12 C11 1.426(6) 16_655
C12 C11 1.426(6) 2_655
C12 C11 1.426(6) 18_545
C12 C11 1.426(6) 3_665
C12 C11 1.426(6) 17
C13 C8 1.403(12) 18_545
