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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/10/4501084.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_4501084
loop_
_publ_author_name
'Roy, Sandipan'
'Biradha, Kumar'
_publ_section_title
;
 Two-Component Supramolecular Organic Hosts as Colorimetric Indicators for
 Aromatic Guests: Visual Molecular Recognition via Cation−π
 Interactions
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4120
_journal_paper_doi               10.1021/cg200690c
_journal_volume                  11
_journal_year                    2011
_chemical_formula_sum            'C60 H40 N2 O16'
_chemical_formula_weight         1044.94
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                114.499(4)
_cell_angle_beta                 100.823(4)
_cell_angle_gamma                98.386(4)
_cell_formula_units_Z            1
_cell_length_a                   8.0203(11)
_cell_length_b                   12.7391(18)
_cell_length_c                   14.0636(19)
_cell_measurement_reflns_used    4203
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.71
_cell_measurement_theta_min      1.66
_cell_volume                     1243.4(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker CCD APEX 2'
_diffrn_measurement_method       hemisphere
_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  0.0524
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14317
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'bright red'
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             542
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         4203
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.954
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.0568
_refine_ls_shift/su_max          0.068
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1458
_refine_ls_wR_factor_ref         0.1698
_reflns_number_gt                2472
_reflns_number_total             4203
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200690c_si_002.cif
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4501084
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O11 O -0.0309(3) 0.1649(2) 0.3176(2) 0.0781(8) Uani 1 1 d .
O12 O 0.1968(3) 0.2565(2) 0.2919(2) 0.0702(7) Uani 1 1 d .
H12O H 0.235(4) 0.326(3) 0.289(2) 0.050 Uiso 1 1 d .
O13 O -0.2386(4) 0.3309(2) -0.0370(2) 0.0937(10) Uani 1 1 d .
O14 O -0.2287(4) 0.5176(2) 0.0605(2) 0.0746(8) Uani 1 1 d .
H14O H -0.239(3) 0.512(2) -0.014(3) 0.050 Uiso 1 1 d .
C11 C -0.0904(4) 0.3250(2) 0.1687(2) 0.0383(7) Uani 1 1 d .
C12 C -0.0711(4) 0.3175(3) 0.2669(2) 0.0458(8) Uani 1 1 d .
C13 C -0.1512(5) 0.3830(3) 0.3432(3) 0.0645(10) Uani 1 1 d .
H13 H -0.1393 0.3765 0.4075 0.077 Uiso 1 1 calc R
C14 C -0.2476(5) 0.4569(3) 0.3254(3) 0.0710(11) Uani 1 1 d .
H14 H -0.3020 0.4992 0.3767 0.085 Uiso 1 1 calc R
C15 C -0.2629(4) 0.4680(3) 0.2314(3) 0.0554(9) Uani 1 1 d .
H15 H -0.3250 0.5200 0.2202 0.066 Uiso 1 1 calc R
C16 C -0.1867(4) 0.4026(2) 0.1527(2) 0.0394(7) Uani 1 1 d .
C17 C 0.0312(5) 0.2385(3) 0.2928(2) 0.0551(9) Uani 1 1 d .
C18 C -0.2178(4) 0.4132(3) 0.0496(2) 0.0436(7) Uani 1 1 d .
O21 O -0.3454(3) 0.1202(2) 0.0740(2) 0.0822(9) Uani 1 1 d .
O22 O -0.3602(3) -0.0187(2) -0.08793(19) 0.0693(8) Uani 1 1 d .
H22O H -0.448(4) -0.053(3) -0.079(2) 0.050 Uiso 1 1 d .
O23 O 0.2965(3) 0.49803(17) 0.13467(16) 0.0518(6) Uani 1 1 d .
O24 O 0.2954(3) 0.43900(18) 0.26186(16) 0.0546(6) Uani 1 1 d .
C21 C -0.0129(4) 0.2503(2) 0.0824(2) 0.0371(7) Uani 1 1 d .
C22 C -0.1045(4) 0.1349(2) 0.0010(2) 0.0384(7) Uani 1 1 d .
C23 C -0.0293(4) 0.0709(3) -0.0791(2) 0.0448(7) Uani 1 1 d .
H23 H -0.0909 -0.0052 -0.1326 0.054 Uiso 1 1 calc R
C24 C 0.1357(4) 0.1190(3) -0.0800(2) 0.0493(8) Uani 1 1 d .
H24 H 0.1861 0.0749 -0.1329 0.059 Uiso 1 1 calc R
C25 C 0.2253(4) 0.2324(3) -0.0022(3) 0.0472(8) Uani 1 1 d .
H25 H 0.3349 0.2657 -0.0044 0.057 Uiso 1 1 calc R
C26 C 0.1545(4) 0.2976(2) 0.0794(2) 0.0380(7) Uani 1 1 d .
C27 C -0.2814(4) 0.0799(3) -0.0012(2) 0.0439(7) Uani 1 1 d .
C28 C 0.2568(4) 0.4197(3) 0.1645(2) 0.0422(7) Uani 1 1 d .
N1 N 0.1780(4) 0.6928(3) 0.2611(2) 0.0595(8) Uani 1 1 d .
H1N H 0.221(4) 0.635(3) 0.210(2) 0.050 Uiso 1 1 d .
C1 C 0.1676(4) 0.6831(3) 0.3503(3) 0.0626(9) Uani 1 1 d .
H1 H 0.1988 0.6200 0.3600 0.075 Uiso 1 1 calc R
C2 C 0.1115(4) 0.7651(3) 0.4275(3) 0.0559(9) Uani 1 1 d .
H2 H 0.1033 0.7573 0.4895 0.067 Uiso 1 1 calc R
C3 C 0.0667(4) 0.8602(3) 0.4145(2) 0.0435(7) Uani 1 1 d .
C4 C 0.0786(4) 0.8656(3) 0.3188(3) 0.0542(8) Uani 1 1 d .
H4 H 0.0486 0.9276 0.3065 0.065 Uiso 1 1 calc R
C5 C 0.1334(4) 0.7812(3) 0.2436(3) 0.0610(9) Uani 1 1 d .
H5 H 0.1399 0.7850 0.1797 0.073 Uiso 1 1 calc R
C6 C 0.0150(4) 0.9506(2) 0.5000(2) 0.0442(7) Uani 1 1 d .
H6 H 0.0023 0.9375 0.5588 0.053 Uiso 1 1 calc R
C101 C 0.5255(5) -0.0851(4) 0.6338(3) 0.0722(11) Uani 1 1 d .
H101 H 0.5268 -0.1005 0.6930 0.087 Uiso 1 1 calc R
C102 C 0.4760(4) 0.0189(3) 0.6362(3) 0.0559(9) Uani 1 1 d .
C103 C 0.4322(5) 0.1014(4) 0.7243(3) 0.0735(11) Uani 1 1 d .
H103 H 0.4312 0.0880 0.7843 0.088 Uiso 1 1 calc R
C104 C 0.3906(5) 0.2016(4) 0.7235(3) 0.0771(12) Uani 1 1 d .
H104 H 0.3637 0.2559 0.7835 0.092 Uiso 1 1 calc R
C105 C 0.3883(4) 0.2226(3) 0.6347(3) 0.0703(11) Uani 1 1 d .
H105 H 0.3587 0.2907 0.6352 0.084 Uiso 1 1 calc R
C106 C 0.4297(4) 0.1435(3) 0.5446(3) 0.0542(8) Uani 1 1 d .
C107 C 0.4762(3) 0.0406(3) 0.5445(2) 0.0438(7) Uani 1 1 d .
C108 C 0.4300(5) 0.1610(4) 0.4506(3) 0.0708(10) Uani 1 1 d .
H108 H 0.3982 0.2274 0.4482 0.085 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'
O O 0.0106 0.0060 '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
C16 C11 C12 118.0(2) . .
C16 C11 C21 120.9(2) . .
C12 C11 C21 121.0(2) . .
C13 C12 C11 120.0(3) . .
C13 C12 C17 117.7(3) . .
C11 C12 C17 122.3(3) . .
C14 C13 C12 121.2(3) . .
C15 C14 C13 119.4(3) . .
C14 C15 C16 120.8(3) . .
C15 C16 C11 120.5(3) . .
C15 C16 C18 118.0(3) . .
C11 C16 C18 121.4(2) . .
O11 C17 O12 120.6(3) . .
O11 C17 C12 122.4(3) . .
O12 C17 C12 116.9(3) . .
O13 C18 O14 122.3(3) . .
O13 C18 C16 123.0(3) . .
O14 C18 C16 114.6(3) . .
C26 C21 C22 118.0(2) . .
C26 C21 C11 119.5(2) . .
C22 C21 C11 122.4(2) . .
C23 C22 C21 120.3(3) . .
C23 C22 C27 118.8(3) . .
C21 C22 C27 120.9(3) . .
C24 C23 C22 120.7(3) . .
C25 C24 C23 119.7(3) . .
C24 C25 C26 120.8(3) . .
C25 C26 C21 120.5(3) . .
C25 C26 C28 119.7(2) . .
C21 C26 C28 119.8(2) . .
O21 C27 O22 122.2(3) . .
O21 C27 C22 123.2(3) . .
O22 C27 C22 114.5(3) . .
O24 C28 O23 123.5(3) . .
O24 C28 C26 118.3(2) . .
O23 C28 C26 118.1(2) . .
C1 N1 C5 121.8(3) . .
N1 C1 C2 120.3(3) . .
C1 C2 C3 120.4(3) . .
C2 C3 C4 117.0(3) . .
C2 C3 C6 120.0(3) . .
C4 C3 C6 123.0(3) . .
C5 C4 C3 120.5(3) . .
N1 C5 C4 120.0(3) . .
C6 C6 C3 124.8(3) 2_576 .
C108 C101 C102 122.2(3) 2_656 .
C103 C102 C107 118.8(3) . .
C103 C102 C101 123.6(3) . .
C107 C102 C101 117.7(3) . .
C104 C103 C102 121.1(4) . .
C103 C104 C105 120.6(4) . .
C104 C105 C106 120.9(4) . .
C105 C106 C107 119.4(3) . .
C105 C106 C108 123.2(3) . .
C107 C106 C108 117.4(3) . .
C106 C107 C107 121.1(3) . 2_656
C106 C107 C102 119.3(3) . .
C107 C107 C102 119.7(4) 2_656 .
C101 C108 C106 122.0(3) 2_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O11 C17 1.205(4) .
O12 C17 1.318(4) .
O13 C18 1.193(3) .
O14 C18 1.293(4) .
C11 C16 1.402(4) .
C11 C12 1.405(4) .
C11 C21 1.506(4) .
C12 C13 1.389(4) .
C12 C17 1.500(4) .
C13 C14 1.372(5) .
C14 C15 1.372(4) .
C15 C16 1.389(4) .
C16 C18 1.490(4) .
O21 C27 1.214(3) .
O22 C27 1.294(4) .
O23 C28 1.256(3) .
O24 C28 1.253(3) .
C21 C26 1.405(4) .
C21 C22 1.408(4) .
C22 C23 1.391(4) .
C22 C27 1.477(4) .
C23 C24 1.380(4) .
C24 C25 1.375(4) .
C25 C26 1.386(4) .
C26 C28 1.497(4) .
N1 C1 1.326(4) .
N1 C5 1.330(4) .
C1 C2 1.362(4) .
C2 C3 1.384(4) .
C3 C4 1.396(4) .
C3 C6 1.457(4) .
C4 C5 1.355(4) .
C6 C6 1.314(5) 2_576
C101 C108 1.333(5) 2_656
C101 C102 1.428(5) .
C102 C103 1.398(5) .
C102 C107 1.426(4) .
C103 C104 1.368(6) .
C104 C105 1.380(6) .
C105 C106 1.389(5) .
C106 C107 1.414(4) .
C106 C108 1.429(5) .
C107 C107 1.416(6) 2_656
C108 C101 1.333(5) 2_656
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144606
