#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/45/7214592.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_7214592
loop_
_publ_author_name
'Nassimbeni, Luigi R.'
'Su, Hong'
_publ_section_title
;
 How to monitor guest exchange in host--guest systems
;
_journal_issue                   37
_journal_name_full               CrystEngComm
_journal_page_first              7396
_journal_paper_doi               10.1039/c3ce40675j
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C20 H16 O3.C3.50 H4'
_chemical_formula_sum            'C23.5 H20 O3'
_chemical_formula_weight         350.40
_chemical_name_systematic
;
?
;
_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                95.557(2)
_cell_angle_beta                 96.234(2)
_cell_angle_gamma                110.261(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3923(3)
_cell_length_b                   9.0879(4)
_cell_length_c                   12.7002(7)
_cell_measurement_reflns_used    15266
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.41
_cell_volume                     893.88(7)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT program (Nonius, 2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       '1.2° φ scans and ω 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  0.1077
_diffrn_reflns_av_sigmaI/netI    0.1547
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15266
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.41
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9874
_exptl_absorpt_correction_T_min  0.9692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourles
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             370
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3119
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.918
_refine_ls_R_factor_all          0.1452
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0382P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1184
_reflns_number_gt                1433
_reflns_number_total             3119
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce40675j.txt
_cod_data_source_block           5
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C23.50 H20 O3'
_cod_database_code               7214592
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
O9 O 0.2815(2) 0.7873(2) 0.53174(14) 0.0300(5) Uani 1 1 d D
H9 H 0.213(4) 0.694(3) 0.481(2) 0.126(15) Uiso 1 1 d D
O10 O -0.0726(2) 0.4878(2) 0.61770(13) 0.0315(5) Uani 1 1 d .
O11 O 0.6845(2) 1.3362(2) 0.90513(15) 0.0435(6) Uani 1 1 d .
C1 C 0.3873(3) 0.6241(3) 0.7226(2) 0.0305(7) Uani 1 1 d .
H1 H 0.4879 0.7170 0.7352 0.037 Uiso 1 1 calc R
C2 C 0.3983(3) 0.4844(3) 0.7501(2) 0.0329(8) Uani 1 1 d .
H2 H 0.5059 0.4813 0.7797 0.039 Uiso 1 1 calc R
C3 C 0.2523(3) 0.3486(3) 0.7345(2) 0.0357(8) Uani 1 1 d .
H3 H 0.2594 0.2522 0.7533 0.043 Uiso 1 1 calc R
C4 C 0.0968(3) 0.3536(3) 0.6916(2) 0.0326(8) Uani 1 1 d .
H4 H -0.0043 0.2613 0.6819 0.039 Uiso 1 1 calc R
C5 C -0.2668(3) 0.6145(3) 0.5792(2) 0.0317(8) Uani 1 1 d .
H5 H -0.3566 0.5136 0.5694 0.038 Uiso 1 1 calc R
C6 C -0.3026(3) 0.7499(4) 0.5663(2) 0.0339(8) Uani 1 1 d .
H6 H -0.4179 0.7422 0.5461 0.041 Uiso 1 1 calc R
C7 C -0.1710(3) 0.8967(3) 0.5827(2) 0.0341(8) Uani 1 1 d .
H7 H -0.1958 0.9898 0.5752 0.041 Uiso 1 1 calc R
C8 C -0.0035(3) 0.9064(3) 0.6100(2) 0.0324(7) Uani 1 1 d .
H8 H 0.0862 1.0075 0.6218 0.039 Uiso 1 1 calc R
C9 C 0.2234(3) 0.7812(3) 0.6359(2) 0.0256(7) Uani 1 1 d .
C11 C 0.2327(3) 0.6327(3) 0.6769(2) 0.0250(7) Uani 1 1 d .
C12 C 0.0890(3) 0.4946(3) 0.6628(2) 0.0267(7) Uani 1 1 d .
C13 C -0.0966(3) 0.6297(3) 0.6069(2) 0.0260(7) Uani 1 1 d .
C14 C 0.0376(3) 0.7722(3) 0.62057(19) 0.0234(7) Uani 1 1 d .
C15 C 0.3451(3) 0.9318(3) 0.7069(2) 0.0237(7) Uani 1 1 d .
C16 C 0.3211(3) 0.9601(3) 0.8123(2) 0.0299(7) Uani 1 1 d .
H16 H 0.2267 0.8870 0.8374 0.036 Uiso 1 1 calc R
C17 C 0.4317(3) 1.0929(3) 0.8822(2) 0.0317(7) Uani 1 1 d .
H17 H 0.4142 1.1096 0.9544 0.038 Uiso 1 1 calc R
C18 C 0.5670(3) 1.1995(3) 0.8447(2) 0.0311(8) Uani 1 1 d .
C19 C 0.5920(3) 1.1747(3) 0.7401(2) 0.0318(7) Uani 1 1 d .
H19 H 0.6852 1.2490 0.7147 0.038 Uiso 1 1 calc R
C20 C 0.4808(3) 1.0410(3) 0.6713(2) 0.0296(7) Uani 1 1 d .
H20 H 0.4987 1.0249 0.5991 0.035 Uiso 1 1 calc R
C21 C 0.6604(4) 1.3686(3) 1.0135(2) 0.0542(10) Uani 1 1 d .
H21A H 0.5485 1.3798 1.0145 0.081 Uiso 1 1 calc R
H21B H 0.7517 1.4672 1.0484 0.081 Uiso 1 1 calc R
H21C H 0.6644 1.2811 1.0518 0.081 Uiso 1 1 calc R
C1G C 0.1363(6) 1.2373(7) 0.0988(5) 0.0993(18) Uani 1 1 d .
C2G C 0.0654(5) 0.9397(7) 0.0632(3) 0.0688(12) Uani 1 1 d .
C3G C 0.0503(9) 1.0784(13) 0.0376(7) 0.068(2) Uani 0.50 1 d P
C4G C 0.1518(10) 1.0934(17) 0.1252(7) 0.099(4) Uani 0.50 1 d P
C5G C 0.0154(14) 1.2102(12) -0.0059(12) 0.109(4) Uani 0.50 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'
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
C9 O9 H9 111(2) . .
C13 O10 C12 118.1(2) . .
C18 O11 C21 116.8(2) . .
C2 C1 C11 121.8(2) . .
C2 C1 H1 119.1 . .
C11 C1 H1 119.1 . .
C1 C2 C3 119.8(3) . .
C1 C2 H2 120.1 . .
C3 C2 H2 120.1 . .
C4 C3 C2 119.9(3) . .
C4 C3 H3 120.1 . .
C2 C3 H3 120.1 . .
C3 C4 C12 119.4(3) . .
C3 C4 H4 120.3 . .
C12 C4 H4 120.3 . .
C6 C5 C13 118.4(3) . .
C6 C5 H5 120.8 . .
C13 C5 H5 120.8 . .
C5 C6 C7 120.3(3) . .
C5 C6 H6 119.9 . .
C7 C6 H6 119.9 . .
C8 C7 C6 119.4(3) . .
C8 C7 H7 120.3 . .
C6 C7 H7 120.3 . .
C7 C8 C14 121.8(3) . .
C7 C8 H8 119.1 . .
C14 C8 H8 119.1 . .
O9 C9 C11 108.2(2) . .
O9 C9 C14 107.99(19) . .
C11 C9 C14 109.5(2) . .
O9 C9 C15 105.7(2) . .
C11 C9 C15 112.3(2) . .
C14 C9 C15 112.9(2) . .
C12 C11 C1 116.7(2) . .
C12 C11 C9 121.1(2) . .
C1 C11 C9 122.0(2) . .
C11 C12 C4 122.3(2) . .
C11 C12 O10 122.2(2) . .
C4 C12 O10 115.5(2) . .
C14 C13 C5 123.1(3) . .
C14 C13 O10 122.4(2) . .
C5 C13 O10 114.5(2) . .
C13 C14 C8 117.0(2) . .
C13 C14 C9 121.4(2) . .
C8 C14 C9 121.4(2) . .
C20 C15 C16 118.2(2) . .
C20 C15 C9 122.6(2) . .
C16 C15 C9 119.1(2) . .
C15 C16 C17 121.8(3) . .
C15 C16 H16 119.1 . .
C17 C16 H16 119.1 . .
C18 C17 C16 118.8(3) . .
C18 C17 H17 120.6 . .
C16 C17 H17 120.6 . .
C19 C18 C17 120.4(2) . .
C19 C18 O11 115.0(3) . .
C17 C18 O11 124.6(2) . .
C18 C19 C20 120.2(3) . .
C18 C19 H19 119.9 . .
C20 C19 H19 119.9 . .
C15 C20 C19 120.6(2) . .
C15 C20 H20 119.7 . .
C19 C20 H20 119.7 . .
O11 C21 H21A 109.5 . .
O11 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
O11 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C4G C1G C3G 53.0(6) . .
C4G C1G C5G 111.8(6) . .
C3G C1G C5G 58.8(5) . .
C3G C2G C5G 127.1(8) . 2_575
C3G C2G C4G 54.7(6) . .
C5G C2G C4G 178.2(8) 2_575 .
C3G C2G C3G 65.3(7) . 2_575
C5G C2G C3G 61.8(7) 2_575 2_575
C4G C2G C3G 120.0(9) . 2_575
C4G C3G C2G 65.0(9) . .
C4G C3G C1G 61.9(7) . .
C2G C3G C1G 126.9(8) . .
C4G C3G C5G 124.5(11) . .
C2G C3G C5G 170.5(10) . .
C1G C3G C5G 62.6(7) . .
C4G C3G C2G 179.5(12) . 2_575
C2G C3G C2G 114.7(7) . 2_575
C1G C3G C2G 118.5(10) . 2_575
C5G C3G C2G 55.8(7) . 2_575
C4G C3G C3G 125.6(16) . 2_575
C2G C3G C3G 60.6(8) . 2_575
C1G C3G C3G 172.5(14) . 2_575
C5G C3G C3G 109.9(12) . 2_575
C2G C3G C3G 54.1(6) 2_575 2_575
C3G C4G C1G 65.1(9) . .
C3G C4G C2G 60.4(6) . .
C1G C4G C2G 125.5(8) . .
C2G C5G C3G 62.4(6) 2_575 .
C2G C5G C1G 121.0(8) 2_575 .
C3G C5G C1G 58.6(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O9 C9 1.458(3) .
O9 H9 0.966(2) .
O10 C13 1.390(3) .
O10 C12 1.391(3) .
O11 C18 1.381(3) .
O11 C21 1.430(3) .
C1 C2 1.379(3) .
C1 C11 1.394(3) .
C1 H1 0.9500 .
C2 C3 1.384(3) .
C2 H2 0.9500 .
C3 C4 1.375(3) .
C3 H3 0.9500 .
C4 C12 1.387(3) .
C4 H4 0.9500 .
C5 C6 1.384(3) .
C5 C13 1.389(3) .
C5 H5 0.9500 .
C6 C7 1.385(3) .
C6 H6 0.9500 .
C7 C8 1.381(3) .
C7 H7 0.9500 .
C8 C14 1.392(3) .
C8 H8 0.9500 .
C9 C11 1.516(3) .
C9 C14 1.523(3) .
C9 C15 1.524(3) .
C11 C12 1.387(3) .
C13 C14 1.371(3) .
C15 C20 1.380(3) .
C15 C16 1.387(3) .
C16 C17 1.395(3) .
C16 H16 0.9500 .
C17 C18 1.378(4) .
C17 H17 0.9500 .
C18 C19 1.377(3) .
C19 C20 1.394(3) .
C19 H19 0.9500 .
C20 H20 0.9500 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C1G C4G 1.426(13) .
C1G C3G 1.467(10) .
C1G C5G 1.527(14) .
C2G C3G 1.376(11) .
C2G C5G 1.381(10) 2_575
C2G C4G 1.434(11) .
C2G C3G 1.479(10) 2_575
C3G C4G 1.291(12) .
C3G C5G 1.470(15) .
C3G C2G 1.479(10) 2_575
C3G C3G 1.543(18) 2_575
C5G C2G 1.381(10) 2_575
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O9 H9 O10 0.966(2) 1.906(3) 2.872(2) 179(3) 2_566
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_4
C11 C1 C2 C3 -1.4(4) . .
C1 C2 C3 C4 0.0(4) . .
C2 C3 C4 C12 1.1(4) . .
C13 C5 C6 C7 -1.1(4) . .
C5 C6 C7 C8 1.3(4) . .
C6 C7 C8 C14 0.6(4) . .
C2 C1 C11 C12 1.6(4) . .
C2 C1 C11 C9 -173.5(2) . .
O9 C9 C11 C12 -96.4(3) . .
C14 C9 C11 C12 21.1(3) . .
C15 C9 C11 C12 147.4(2) . .
O9 C9 C11 C1 78.5(3) . .
C14 C9 C11 C1 -164.0(2) . .
C15 C9 C11 C1 -37.8(3) . .
C1 C11 C12 C4 -0.5(4) . .
C9 C11 C12 C4 174.6(2) . .
C1 C11 C12 O10 -179.8(2) . .
C9 C11 C12 O10 -4.6(4) . .
C3 C4 C12 C11 -0.9(4) . .
C3 C4 C12 O10 178.5(2) . .
C13 O10 C12 C11 -13.3(3) . .
C13 O10 C12 C4 167.4(2) . .
C6 C5 C13 C14 -1.0(4) . .
C6 C5 C13 O10 -179.7(2) . .
C12 O10 C13 C14 12.1(3) . .
C12 O10 C13 C5 -169.2(2) . .
C5 C13 C14 C8 2.8(4) . .
O10 C13 C14 C8 -178.6(2) . .
C5 C13 C14 C9 -171.5(2) . .
O10 C13 C14 C9 7.1(4) . .
C7 C8 C14 C13 -2.6(4) . .
C7 C8 C14 C9 171.7(2) . .
O9 C9 C14 C13 95.3(3) . .
C11 C9 C14 C13 -22.4(3) . .
C15 C9 C14 C13 -148.3(2) . .
O9 C9 C14 C8 -78.8(3) . .
C11 C9 C14 C8 163.6(2) . .
C15 C9 C14 C8 37.7(3) . .
O9 C9 C15 C20 -1.5(3) . .
C11 C9 C15 C20 116.3(3) . .
C14 C9 C15 C20 -119.3(3) . .
O9 C9 C15 C16 179.6(2) . .
C11 C9 C15 C16 -62.6(3) . .
C14 C9 C15 C16 61.8(3) . .
C20 C15 C16 C17 -1.3(4) . .
C9 C15 C16 C17 177.7(2) . .
C15 C16 C17 C18 0.9(4) . .
C16 C17 C18 C19 0.0(4) . .
C16 C17 C18 O11 179.3(2) . .
C21 O11 C18 C19 178.3(2) . .
C21 O11 C18 C17 -1.0(4) . .
C17 C18 C19 C20 -0.3(4) . .
O11 C18 C19 C20 -179.7(2) . .
C16 C15 C20 C19 0.9(4) . .
C9 C15 C20 C19 -178.0(2) . .
C18 C19 C20 C15 -0.2(4) . .
C5G C2G C3G C4G 179.9(6) 2_575 .
C3G C2G C3G C4G -179.7(7) 2_575 .
C5G C2G C3G C1G 179.9(5) 2_575 .
C4G C2G C3G C1G 0.0(6) . .
C3G C2G C3G C1G -179.7(9) 2_575 .
C5G C2G C3G C5G -2(4) 2_575 .
C4G C2G C3G C5G 178(4) . .
C3G C2G C3G C5G -2(3) 2_575 .
C5G C2G C3G C2G -0.4(7) 2_575 2_575
C4G C2G C3G C2G 179.7(7) . 2_575
C3G C2G C3G C2G 0.0 2_575 2_575
C5G C2G C3G C3G -0.4(7) 2_575 2_575
C4G C2G C3G C3G 179.7(7) . 2_575
C5G C1G C3G C4G 179.6(7) . .
C4G C1G C3G C2G 0.0(6) . .
C5G C1G C3G C2G 179.6(8) . .
C4G C1G C3G C5G -179.6(7) . .
C4G C1G C3G C2G -179.7(7) . 2_575
C5G C1G C3G C2G -0.1(5) . 2_575
C4G C1G C3G C3G -178(6) . 2_575
C5G C1G C3G C3G 1(5) . 2_575
C2G C3G C4G C1G -180.0(5) . .
C5G C3G C4G C1G 0.5(7) . .
C2G C3G C4G C1G 140(100) 2_575 .
C3G C3G C4G C1G 179.7(9) 2_575 .
C1G C3G C4G C2G 180.0(5) . .
C5G C3G C4G C2G -179.6(8) . .
C2G C3G C4G C2G -40(100) 2_575 .
C3G C3G C4G C2G -0.3(7) 2_575 .
C5G C1G C4G C3G -0.4(6) . .
C3G C1G C4G C2G 0.0(6) . .
C5G C1G C4G C2G -0.4(9) . .
C5G C2G C4G C3G -178(100) 2_575 .
C3G C2G C4G C3G 0.3(7) 2_575 .
C3G C2G C4G C1G 0.0(6) . .
C5G C2G C4G C1G -178(100) 2_575 .
C3G C2G C4G C1G 0.4(9) 2_575 .
C4G C3G C5G C2G 179.6(7) . 2_575
C2G C3G C5G C2G 2(4) . 2_575
C1G C3G C5G C2G -179.9(5) . 2_575
C3G C3G C5G C2G 0.3(6) 2_575 2_575
C4G C3G C5G C1G -0.5(7) . .
C2G C3G C5G C1G -178(4) . .
C2G C3G C5G C1G 179.9(5) 2_575 .
C3G C3G C5G C1G -179.8(7) 2_575 .
C4G C1G C5G C2G 0.5(9) . 2_575
C3G C1G C5G C2G 0.1(5) . 2_575
C4G C1G C5G C3G 0.4(6) . .
