#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:52:37 +0200 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/22/85/7228519.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_7228519
loop_
_publ_author_name
'Sykes, Nicole Margaret'
'Su, Hong'
'Weber, Edwin'
'Bourne, Susan A.'
'Nassimbeni, Luigi'
_publ_section_title
;
 Selectivity of Aliphatic Alcohols by Host-Guest Chemistry
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00736A
_journal_year                    2017
_chemical_formula_moiety         'C28 H18 O2, C5 H12 O1, C5 H12 O1'
_chemical_formula_sum            'C38 H42 O4'
_chemical_formula_weight         562.72
_chemical_name_systematic
; 
9,9'-(ethyne-1,2-diyl)-bis(fluoren-9-ol) bis (2-pentanol) Clathrate
;
_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
_audit_update_record
;
2017-03-25 deposited with the CCDC.
2017-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                101.52(3)
_cell_angle_beta                 103.71(3)
_cell_angle_gamma                114.49(3)
_cell_formula_units_Z            1
_cell_length_a                   8.5130(17)
_cell_length_b                   9.5480(19)
_cell_length_c                   12.017(2)
_cell_measurement_reflns_used    11684
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      1.85
_cell_volume                     813.0(5)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2004)'
_computing_molecular_graphics    'X-seed (Barbour, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Kappa Duo Apex II 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  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11684
_diffrn_reflns_theta_full        27.94
_diffrn_reflns_theta_max         27.94
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9792
_exptl_absorpt_correction_T_min  0.9672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             302
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3865
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0455
_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)+(0.0589P)²+0.1696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1209
_reflns_number_gt                3211
_reflns_number_total             3865
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce00736a2.cif
_cod_data_source_block           H_2_2PENT
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        813.1(3)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7228519
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O13 O -0.27781(10) 0.09223(10) -0.01703(7) 0.0313(2) Uani 1 1 d D . .
O16 O -0.56800(11) 0.13995(11) -0.08821(8) 0.0374(2) Uani 1 1 d D . .
C1 C -0.09222(14) 0.19860(13) -0.13920(10) 0.0270(2) Uani 1 1 d . . .
C2 C 0.04791(17) 0.35517(14) -0.06937(12) 0.0359(3) Uani 1 1 d . . .
H2 H 0.0965 0.3867 0.0168 0.043 Uiso 1 1 calc R . .
C3 C 0.1162(2) 0.46560(16) -0.12846(15) 0.0475(3) Uani 1 1 d . . .
H3 H 0.2121 0.5741 -0.0822 0.057 Uiso 1 1 calc R . .
C4 C 0.0457(2) 0.41878(18) -0.25382(15) 0.0503(4) Uani 1 1 d . . .
H4 H 0.0936 0.4959 -0.2925 0.060 Uiso 1 1 calc R . .
C5 C -0.09440(19) 0.26074(17) -0.32437(13) 0.0427(3) Uani 1 1 d . . .
H5 H -0.1420 0.2292 -0.4105 0.051 Uiso 1 1 calc R . .
C6 C -0.16292(15) 0.15028(14) -0.26586(10) 0.0302(2) Uani 1 1 d . . .
C7 C -0.30482(15) -0.02296(15) -0.31456(10) 0.0307(3) Uani 1 1 d . . .
C8 C -0.41092(18) -0.12809(17) -0.43359(12) 0.0418(3) Uani 1 1 d . . .
H8 H -0.4003 -0.0902 -0.5002 0.050 Uiso 1 1 calc R . .
C9 C -0.53287(19) -0.28995(18) -0.45304(13) 0.0487(3) Uani 1 1 d . . .
H9 H -0.6060 -0.3633 -0.5339 0.058 Uiso 1 1 calc R . .
C10 C -0.54943(18) -0.34592(17) -0.35659(13) 0.0475(3) Uani 1 1 d . . .
H10 H -0.6339 -0.4570 -0.3721 0.057 Uiso 1 1 calc R . .
C11 C -0.44369(16) -0.24126(15) -0.23687(12) 0.0384(3) Uani 1 1 d . . .
H11 H -0.4553 -0.2795 -0.1705 0.046 Uiso 1 1 calc R . .
C12 C -0.32169(14) -0.08065(14) -0.21737(10) 0.0282(2) Uani 1 1 d . . .
C13 C -0.18795(13) 0.05642(13) -0.09651(10) 0.0255(2) Uani 1 1 d . . .
C14 C -0.05423(14) 0.01562(13) -0.02837(10) 0.0266(2) Uani 1 1 d . . .
C15 C -0.5353(7) 0.3077(5) -0.2083(5) 0.0750(15) Uani 0.804(4) 1 d P A 1
H15A H -0.4749 0.4007 -0.1324 0.113 Uiso 0.804(4) 1 calc PR A 1
H15B H -0.6006 0.3332 -0.2733 0.113 Uiso 0.804(4) 1 calc PR A 1
H15C H -0.4419 0.2861 -0.2304 0.113 Uiso 0.804(4) 1 calc PR A 1
C15B C -0.5287(13) 0.3098(9) -0.2177(10) 0.022(2) Uiso 0.196(4) 1 d PD A 2
H15D H -0.5763 0.3078 -0.3010 0.033 Uiso 0.196(4) 1 calc PR A 2
H15E H -0.3941 0.3562 -0.1908 0.033 Uiso 0.196(4) 1 calc PR A 2
H15F H -0.5597 0.3771 -0.1636 0.033 Uiso 0.196(4) 1 calc PR A 2
C16 C -0.6687(2) 0.16184(19) -0.19148(15) 0.0332(4) Uani 0.804(4) 1 d P A 1
H16 H -0.7636 0.1863 -0.1705 0.040 Uiso 0.804(4) 1 calc PR A 1
C16B C -0.6121(12) 0.1438(8) -0.2143(7) 0.0392(19) Uiso 0.196(4) 1 d PD A 2
H16B H -0.5466 0.0927 -0.2510 0.047 Uiso 0.196(4) 1 calc PR A 2
C17 C -0.7695(3) 0.0064(2) -0.30220(17) 0.0371(4) Uani 0.804(4) 1 d P A 1
H17A H -0.8287 0.0287 -0.3729 0.044 Uiso 0.804(4) 1 calc PR A 1
H17B H -0.6778 -0.0231 -0.3209 0.044 Uiso 0.804(4) 1 calc PR A 1
C17B C -0.8088(14) 0.0285(12) -0.2816(10) 0.049(3) Uiso 0.196(4) 1 d P A 2
H17C H -0.8493 0.0513 -0.3570 0.059 Uiso 0.196(4) 1 calc PR A 2
H17D H -0.8808 0.0452 -0.2316 0.059 Uiso 0.196(4) 1 calc PR A 2
C18 C -0.9161(3) -0.1382(2) -0.28566(16) 0.0429(5) Uani 0.804(4) 1 d P A 1
H18A H -0.8546 -0.1726 -0.2244 0.051 Uiso 0.804(4) 1 calc PR A 1
H18B H -0.9956 -0.1031 -0.2535 0.051 Uiso 0.804(4) 1 calc PR A 1
C18B C -0.8509(12) -0.1518(9) -0.3153(8) 0.045(2) Uiso 0.196(4) 1 d P A 2
H18C H -0.8052 -0.1740 -0.2407 0.054 Uiso 0.196(4) 1 calc PR A 2
H18D H -0.7855 -0.1712 -0.3697 0.054 Uiso 0.196(4) 1 calc PR A 2
C19 C -1.0363(3) -0.2827(3) -0.4015(2) 0.0542(6) Uani 0.804(4) 1 d P A 1
H19A H -1.0941 -0.2488 -0.4637 0.081 Uiso 0.804(4) 1 calc PR A 1
H19B H -1.1325 -0.3689 -0.3858 0.081 Uiso 0.804(4) 1 calc PR A 1
H19C H -0.9602 -0.3244 -0.4302 0.081 Uiso 0.804(4) 1 calc PR A 1
C19B C -1.0629(8) -0.270(2) -0.3804(11) 0.131(10) Uiso 0.196(4) 1 d P A 2
H19D H -1.1269 -0.2549 -0.3249 0.197 Uiso 0.196(4) 1 calc PR A 2
H19E H -1.0866 -0.3831 -0.4041 0.197 Uiso 0.196(4) 1 calc PR A 2
H19F H -1.1086 -0.2458 -0.4531 0.197 Uiso 0.196(4) 1 calc PR A 2
H13 H -0.3778 0.1102 -0.0565 0.088(6) Uiso 1 1 d RD . .
H16' H -0.6577 0.0545 -0.0699 0.113(8) Uiso 1 1 d RD . .
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
C16 O16 C16B 26.5(3) .
C2 C1 C6 121.32(11) .
C2 C1 C13 128.19(11) .
C6 C1 C13 110.47(10) .
C1 C2 C3 118.32(13) .
C4 C3 C2 120.59(13) .
C3 C4 C5 121.18(13) .
C6 C5 C4 118.43(13) .
C5 C6 C1 120.15(12) .
C5 C6 C7 131.02(12) .
C1 C6 C7 108.81(11) .
C8 C7 C12 120.11(11) .
C8 C7 C6 131.07(12) .
C12 C7 C6 108.80(10) .
C9 C8 C7 118.52(13) .
C10 C9 C8 121.06(13) .
C9 C10 C11 120.80(13) .
C12 C11 C10 118.22(13) .
C11 C12 C7 121.28(11) .
C11 C12 C13 128.54(11) .
C7 C12 C13 110.18(10) .
O13 C13 C14 106.46(9) .
O13 C13 C1 112.51(9) .
C14 C13 C1 111.16(9) .
O13 C13 C12 113.54(8) .
C14 C13 C12 111.55(9) .
C1 C13 C12 101.73(9) .
C14 C14 C13 178.95(16) 2
O16 C16 C15 106.7(2) .
O16 C16 C17 111.09(14) .
C15 C16 C17 115.0(2) .
C15B C16B C17B 121.3(8) .
C15B C16B O16 112.3(7) .
C17B C16B O16 107.9(7) .
C18 C17 C16 113.87(19) .
C16B C17B C18B 112.5(9) .
C19 C18 C17 113.54(19) .
C17B C18B C19B 110.6(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O13 C13 1.4307(13) .
O16 C16 1.4375(17) .
O16 C16B 1.483(7) .
C1 C2 1.3813(18) .
C1 C6 1.3953(17) .
C1 C13 1.5263(15) .
C2 C3 1.3930(18) .
C3 C4 1.382(2) .
C4 C5 1.391(2) .
C5 C6 1.3885(17) .
C6 C7 1.4696(18) .
C7 C8 1.3900(19) .
C7 C12 1.3996(16) .
C8 C9 1.390(2) .
C9 C10 1.382(2) .
C10 C11 1.395(2) .
C11 C12 1.3806(17) .
C12 C13 1.5298(18) .
C13 C14 1.4736(15) .
C14 C14 1.191(2) 2
C15 C16 1.477(4) .
C15B C16B 1.458(5) .
C16 C17 1.524(3) .
C16B C17B 1.465(13) .
C17 C18 1.517(3) .
C17B C18B 1.548(13) .
C18 C19 1.508(3) .
C18B C19B 1.560(10) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139203617
