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#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/67/7106779.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_7106779
loop_
_publ_author_name
'Li-Xia Wang'
'Liang Zhao'
'De-Xian Wang'
'Mei-Xiang Wang'
_publ_section_title
;
 Synthesis of 1,3,5-alternate azacalix[3]pyridine[3]pyrimidine and its
 complexation with fullerenes via multiple p/p and CH/p interactions
;
_journal_name_full               Chem.Commun.
_journal_page_first              9690
_journal_paper_doi               10.1039/c1cc11514f
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C33 H33 N15'
_chemical_formula_weight         639.74
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_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            6
_cell_length_a                   15.180(2)
_cell_length_b                   15.180(2)
_cell_length_c                   27.583(6)
_cell_measurement_temperature    173(2)
_cell_volume                     5504.5(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0575
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            5464
_diffrn_reflns_theta_full        27.41
_diffrn_reflns_theta_max         27.41
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9704
_exptl_absorpt_correction_T_min  0.9704
_exptl_absorpt_correction_type   numerical
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0783
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0901P)²+15.1661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1914
_refine_ls_wR_factor_ref         0.2049
_reflns_number_gt                1926
_reflns_number_total             2800
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc11514f.txt
_cod_data_source_block           Py3Pm3
_cod_original_cell_volume        5504.3(15)
_cod_original_sg_symbol_H-M      R-3
_cod_database_code               7106779
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.86338(18) 0.79954(17) 0.06454(8) 0.0283(5) Uani 1 1 d . . .
N2 N 0.54629(17) 0.51700(17) 0.07985(8) 0.0261(5) Uani 1 1 d . . .
N3 N 1.00437(18) 0.77074(17) 0.05662(8) 0.0278(5) Uani 1 1 d . . .
N4 N 0.70121(18) 0.66785(16) 0.08397(9) 0.0296(6) Uani 1 1 d . . .
N5 N 0.99087(18) 0.61460(19) 0.07154(9) 0.0327(6) Uani 1 1 d . . .
C8 C 0.6340(2) 0.5712(2) 0.10416(10) 0.0265(6) Uani 1 1 d . . .
C9 C 0.9435(2) 0.6728(2) 0.06970(9) 0.0263(6) Uani 1 1 d . . .
C10 C 0.9594(2) 0.8268(2) 0.05486(10) 0.0284(6) Uani 1 1 d . . .
H10A H 1.0018 0.8956 0.0454 0.034 Uiso 1 1 calc R . .
C11 C 0.4913(2) 0.3887(2) 0.14123(10) 0.0323(7) Uani 1 1 d . . .
H11A H 0.4398 0.3255 0.1538 0.039 Uiso 1 1 calc R . .
C12 C 0.6559(2) 0.5379(2) 0.14663(10) 0.0306(6) Uani 1 1 d . . .
H12A H 0.7193 0.5775 0.1626 0.037 Uiso 1 1 calc R . .
C13 C 0.8408(2) 0.6329(2) 0.07827(10) 0.0279(6) Uani 1 1 d . . .
H13A H 0.7977 0.5628 0.0854 0.033 Uiso 1 1 calc R . .
C14 C 0.8030(2) 0.7001(2) 0.07606(9) 0.0241(6) Uani 1 1 d . . .
C15 C 0.5823(2) 0.4448(2) 0.16539(10) 0.0325(7) Uani 1 1 d . . .
H15A H 0.5946 0.4201 0.1947 0.039 Uiso 1 1 calc R . .
C16 C 0.4769(2) 0.4270(2) 0.09771(10) 0.0261(6) Uani 1 1 d . . .
C17 C 0.6580(2) 0.7289(2) 0.06659(11) 0.0335(7) Uani 1 1 d . . .
H17A H 0.7125 0.7937 0.0539 0.050 Uiso 1 1 calc R . .
H17B H 0.6237 0.7420 0.0934 0.050 Uiso 1 1 calc R . .
H17C H 0.6088 0.6921 0.0408 0.050 Uiso 1 1 calc R . .
C18 C 1.0839(2) 0.6455(2) 0.04411(12) 0.0382(7) Uani 1 1 d . . .
H18A H 1.1067 0.5962 0.0493 0.057 Uiso 1 1 calc R . .
H18B H 1.1368 0.7129 0.0550 0.057 Uiso 1 1 calc R . .
H18C H 1.0706 0.6482 0.0095 0.057 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 0.0033 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'
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
C10 N1 C14 114.8(2) . . ?
C16 N2 C8 118.4(2) . . ?
C10 N3 C9 115.2(2) . . ?
C14 N4 C8 121.7(2) . . ?
C14 N4 C17 120.0(2) . . ?
C8 N4 C17 117.9(2) . . ?
C9 N5 C16 122.3(2) . 3_665 ?
C9 N5 C18 120.1(2) . . ?
C16 N5 C18 117.5(2) 3_665 . ?
N2 C8 C12 123.1(3) . . ?
N2 C8 N4 114.7(2) . . ?
C12 C8 N4 122.2(3) . . ?
N3 C9 C13 122.0(3) . . ?
N3 C9 N5 115.0(2) . . ?
C13 C9 N5 122.9(3) . . ?
N1 C10 N3 128.8(3) . . ?
N1 C10 H10A 115.6 . . ?
N3 C10 H10A 115.6 . . ?
C15 C11 C16 118.3(3) . . ?
C15 C11 H11A 120.8 . . ?
C16 C11 H11A 120.8 . . ?
C8 C12 C15 118.0(3) . . ?
C8 C12 H12A 121.0 . . ?
C15 C12 H12A 121.0 . . ?
C9 C13 C14 117.2(3) . . ?
C9 C13 H13A 121.4 . . ?
C14 C13 H13A 121.4 . . ?
N1 C14 N4 116.4(2) . . ?
N1 C14 C13 121.7(3) . . ?
N4 C14 C13 121.8(2) . . ?
C11 C15 C12 119.7(3) . . ?
C11 C15 H15A 120.1 . . ?
C12 C15 H15A 120.1 . . ?
N2 C16 C11 122.4(3) . . ?
N2 C16 N5 115.5(2) . 2_655 ?
C11 C16 N5 122.0(2) . 2_655 ?
N4 C17 H17A 109.5 . . ?
N4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N5 C18 H18A 109.5 . . ?
N5 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N5 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
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
N1 C10 1.329(4) . ?
N1 C14 1.355(3) . ?
N2 C16 1.334(3) . ?
N2 C8 1.343(3) . ?
N3 C10 1.331(4) . ?
N3 C9 1.349(3) . ?
N4 C14 1.385(4) . ?
N4 C8 1.417(3) . ?
N4 C17 1.458(4) . ?
N5 C9 1.391(4) . ?
N5 C16 1.405(4) 3_665 ?
N5 C18 1.457(4) . ?
C8 C12 1.380(4) . ?
C9 C13 1.381(4) . ?
C10 H10A 0.9500 . ?
C11 C15 1.378(4) . ?
C11 C16 1.398(4) . ?
C11 H11A 0.9500 . ?
C12 C15 1.391(4) . ?
C12 H12A 0.9500 . ?
C13 C14 1.401(4) . ?
C13 H13A 0.9500 . ?
C15 H15A 0.9500 . ?
C16 N5 1.405(4) 2_655 ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
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
C16 N2 C8 C12 0.2(4) . . . . ?
C16 N2 C8 N4 -177.0(2) . . . . ?
C14 N4 C8 N2 -131.1(3) . . . . ?
C17 N4 C8 N2 42.3(3) . . . . ?
C14 N4 C8 C12 51.7(4) . . . . ?
C17 N4 C8 C12 -135.0(3) . . . . ?
C10 N3 C9 C13 3.0(4) . . . . ?
C10 N3 C9 N5 -179.9(2) . . . . ?
C16 N5 C9 N3 160.3(2) 3_665 . . . ?
C18 N5 C9 N3 -22.3(4) . . . . ?
C16 N5 C9 C13 -22.7(4) 3_665 . . . ?
C18 N5 C9 C13 154.7(3) . . . . ?
C14 N1 C10 N3 -2.6(4) . . . . ?
C9 N3 C10 N1 0.5(4) . . . . ?
N2 C8 C12 C15 -1.3(4) . . . . ?
N4 C8 C12 C15 175.7(3) . . . . ?
N3 C9 C13 C14 -4.2(4) . . . . ?
N5 C9 C13 C14 179.0(2) . . . . ?
C10 N1 C14 N4 -176.8(2) . . . . ?
C10 N1 C14 C13 1.1(4) . . . . ?
C8 N4 C14 N1 -169.1(2) . . . . ?
C17 N4 C14 N1 17.7(4) . . . . ?
C8 N4 C14 C13 13.0(4) . . . . ?
C17 N4 C14 C13 -160.2(3) . . . . ?
C9 C13 C14 N1 2.0(4) . . . . ?
C9 C13 C14 N4 179.9(2) . . . . ?
C16 C11 C15 C12 1.1(4) . . . . ?
C8 C12 C15 C11 0.6(4) . . . . ?
C8 N2 C16 C11 1.6(4) . . . . ?
C8 N2 C16 N5 177.6(2) . . . 2_655 ?
C15 C11 C16 N2 -2.3(4) . . . . ?
C15 C11 C16 N5 -178.0(3) . . . 2_655 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101959939
