#------------------------------------------------------------------------------
#$Date: 2017-09-19 05:46:45 +0300 (Tue, 19 Sep 2017) $
#$Revision: 201006 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/91/7229181.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_7229181
loop_
_publ_author_name
'Sykes, Nicole Margaret'
'Su, Hong'
'Weber, Edwin'
'Bourne, Susan A.'
'Nassimbeni, Luigi'
_publ_section_title
;
 Crystallisation Temperature Control of Stoichiometry and Selectivity in
 Host- Guest Compounds
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE01414G
_journal_year                    2017
_chemical_formula_moiety         'C28 H18 O2, 4 (C4 H10 O1)'
_chemical_formula_sum            'C44 H58 O6'
_chemical_formula_weight         682.90
_chemical_name_systematic
'9,9?-(ethyne-1,2-diyl)-bis(fluoren-9-ol) tetra (2-methyl-2-propanoll) 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
;
2017-06-23 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                111.38(3)
_cell_angle_beta                 96.88(3)
_cell_angle_gamma                95.54(3)
_cell_formula_units_Z            1
_cell_length_a                   9.4041(19)
_cell_length_b                   9.4706(19)
_cell_length_c                   12.423(3)
_cell_measurement_reflns_used    13319
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.00
_cell_measurement_theta_min      1.79
_cell_volume                     1011.0(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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0385
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13319
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             370
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4885
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0574
_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)+(0.0664P)²+0.3302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1363
_refine_ls_wR_factor_ref         0.1537
_reflns_number_gt                3458
_reflns_number_total             4885
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce01414g3.cif
_cod_data_source_block           structure4
_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        1011.0(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7229181
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
O13 O -0.07781(13) 0.23057(12) -0.08248(9) 0.0285(3) Uani 1 1 d D
O20 O -0.06958(13) 0.35942(13) -0.24160(10) 0.0319(3) Uani 1 1 d D
H20 H 0.0121(16) 0.4427(18) -0.2072(18) 0.059(7) Uiso 1 1 d D
H13 H -0.074(3) 0.272(2) -0.1438(14) 0.066(7) Uiso 1 1 d D
H16 H 0.119(3) 0.669(2) -0.0629(10) 0.070(7) Uiso 1 1 d D
C13 C -0.03921(17) 0.08071(17) -0.13279(12) 0.0239(3) Uani 1 1 d .
C14 C -0.01233(17) 0.02394(17) -0.03791(12) 0.0246(3) Uani 1 1 d .
O16 O 0.13777(15) 0.60877(16) -0.13984(12) 0.0505(4) Uani 1 1 d D
C1 C 0.09255(18) 0.07960(17) -0.19370(13) 0.0247(3) Uani 1 1 d .
C12 C -0.15498(18) -0.02847(17) -0.23398(13) 0.0248(3) Uani 1 1 d .
C6 C 0.05636(19) -0.01527(18) -0.31264(13) 0.0269(4) Uani 1 1 d .
C7 C -0.09723(19) -0.08227(18) -0.33736(13) 0.0266(4) Uani 1 1 d .
C11 C -0.29863(19) -0.0707(2) -0.23263(15) 0.0323(4) Uani 1 1 d .
H11 H -0.3374 -0.0337 -0.1620 0.039 Uiso 1 1 calc R
C2 C 0.23037(19) 0.1576(2) -0.14606(15) 0.0328(4) Uani 1 1 d .
H2 H 0.2542 0.2220 -0.0653 0.039 Uiso 1 1 calc R
C5 C 0.1600(2) -0.0304(2) -0.38485(15) 0.0352(4) Uani 1 1 d .
H5 H 0.1362 -0.0934 -0.4659 0.042 Uiso 1 1 calc R
C10 C -0.3862(2) -0.1692(2) -0.33713(16) 0.0376(4) Uani 1 1 d .
H10 H -0.4860 -0.1988 -0.3383 0.045 Uiso 1 1 calc R
C8 C -0.1840(2) -0.1819(2) -0.44107(14) 0.0354(4) Uani 1 1 d .
H8 H -0.1452 -0.2201 -0.5116 0.042 Uiso 1 1 calc R
C20 C -0.1957(2) 0.4120(2) -0.28239(15) 0.0333(4) Uani 1 1 d .
C16 C 0.2835(2) 0.6411(2) -0.15291(15) 0.0350(4) Uani 1 1 d .
C3 C 0.3342(2) 0.1399(2) -0.21916(17) 0.0395(4) Uani 1 1 d .
H3 H 0.4305 0.1918 -0.1879 0.047 Uiso 1 1 calc R
C4 C 0.2983(2) 0.0475(2) -0.33707(16) 0.0400(5) Uani 1 1 d .
H4 H 0.3702 0.0375 -0.3859 0.048 Uiso 1 1 calc R
C9 C -0.3278(2) -0.2238(2) -0.43910(16) 0.0403(5) Uani 1 1 d .
H9 H -0.3883 -0.2919 -0.5094 0.048 Uiso 1 1 calc R
C19 C -0.1663(3) 0.4572(3) -0.3834(2) 0.0612(7) Uani 1 1 d .
H19A H -0.0872 0.5439 -0.3556 0.092 Uiso 1 1 calc R
H19B H -0.2538 0.4869 -0.4152 0.092 Uiso 1 1 calc R
H19C H -0.1387 0.3701 -0.4448 0.092 Uiso 1 1 calc R
C21 C -0.3163(2) 0.2773(2) -0.32011(19) 0.0489(5) Uani 1 1 d .
H21A H -0.2904 0.1894 -0.3820 0.073 Uiso 1 1 calc R
H21B H -0.4061 0.3052 -0.3499 0.073 Uiso 1 1 calc R
H21C H -0.3304 0.2500 -0.2528 0.073 Uiso 1 1 calc R
C15 C 0.2985(3) 0.5335(3) -0.27372(17) 0.0531(6) Uani 1 1 d .
H15A H 0.2699 0.4273 -0.2819 0.080 Uiso 1 1 calc R
H15B H 0.3995 0.5477 -0.2850 0.080 Uiso 1 1 calc R
H15C H 0.2359 0.5555 -0.3328 0.080 Uiso 1 1 calc R
C22 C -0.2287(3) 0.5493(3) -0.1831(2) 0.0553(6) Uani 1 1 d .
H22A H -0.2443 0.5200 -0.1169 0.083 Uiso 1 1 calc R
H22B H -0.3162 0.5835 -0.2102 0.083 Uiso 1 1 calc R
H22C H -0.1469 0.6329 -0.1580 0.083 Uiso 1 1 calc R
C18 C 0.3200(3) 0.8046(3) -0.1366(3) 0.0753(9) Uani 1 1 d .
H18A H 0.2617 0.8240 -0.1991 0.113 Uiso 1 1 calc R
H18B H 0.4231 0.8271 -0.1394 0.113 Uiso 1 1 calc R
H18C H 0.2992 0.8705 -0.0604 0.113 Uiso 1 1 calc R
C17 C 0.3792(3) 0.6096(4) -0.0597(2) 0.0790(9) Uani 1 1 d .
H17A H 0.3586 0.6708 0.0178 0.118 Uiso 1 1 calc R
H17B H 0.4811 0.6371 -0.0633 0.118 Uiso 1 1 calc R
H17C H 0.3597 0.5003 -0.0734 0.118 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'
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
O13 C13 C14 107.36(12) .
O13 C13 C1 112.63(13) .
C14 C13 C1 111.02(13) .
O13 C13 C12 112.35(13) .
C14 C13 C12 112.01(13) .
C1 C13 C12 101.52(12) .
C14 C14 C13 178.3(2) 2
C2 C1 C6 121.23(16) .
C2 C1 C13 128.27(14) .
C6 C1 C13 110.49(14) .
C11 C12 C7 121.05(15) .
C11 C12 C13 128.44(14) .
C7 C12 C13 110.48(14) .
C5 C6 C1 119.93(16) .
C5 C6 C7 131.37(15) .
C1 C6 C7 108.69(14) .
C8 C7 C12 120.32(17) .
C8 C7 C6 130.88(16) .
C12 C7 C6 108.81(14) .
C12 C11 C10 118.60(17) .
C1 C2 C3 118.33(16) .
C4 C5 C6 118.84(16) .
C9 C10 C11 120.06(18) .
C9 C8 C7 118.33(17) .
O20 C20 C19 108.83(17) .
O20 C20 C21 105.16(15) .
C19 C20 C21 111.98(17) .
O20 C20 C22 109.43(15) .
C19 C20 C22 109.99(18) .
C21 C20 C22 111.29(17) .
O16 C16 C18 110.54(18) .
O16 C16 C15 106.64(15) .
C18 C16 C15 112.04(18) .
O16 C16 C17 107.56(18) .
C18 C16 C17 109.3(2) .
C15 C16 C17 110.63(19) .
C4 C3 C2 120.53(18) .
C5 C4 C3 121.12(17) .
C8 C9 C10 121.63(16) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O13 C13 1.4295(18) .
O20 C20 1.437(2) .
C13 C14 1.469(2) .
C13 C1 1.526(2) .
C13 C12 1.530(2) .
C14 C14 1.194(3) 2
O16 C16 1.417(2) .
C1 C2 1.374(2) .
C1 C6 1.400(2) .
C12 C11 1.375(2) .
C12 C7 1.395(2) .
C6 C5 1.385(2) .
C6 C7 1.469(2) .
C7 C8 1.389(2) .
C11 C10 1.395(2) .
C2 C3 1.392(3) .
C5 C4 1.377(3) .
C10 C9 1.385(3) .
C8 C9 1.377(3) .
C20 C19 1.512(3) .
C20 C21 1.513(3) .
C20 C22 1.519(3) .
C16 C18 1.486(3) .
C16 C15 1.508(2) .
C16 C17 1.514(3) .
C3 C4 1.384(3) .
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_4
O13 C13 C14 C14 -143(8) 2
C1 C13 C14 C14 -19(8) 2
C12 C13 C14 C14 93(8) 2
O13 C13 C1 C2 59.7(2) .
C14 C13 C1 C2 -60.7(2) .
C12 C13 C1 C2 -179.96(16) .
O13 C13 C1 C6 -119.81(14) .
C14 C13 C1 C6 119.77(14) .
C12 C13 C1 C6 0.56(16) .
O13 C13 C12 C11 -58.1(2) .
C14 C13 C12 C11 62.9(2) .
C1 C13 C12 C11 -178.64(16) .
O13 C13 C12 C7 120.05(14) .
C14 C13 C12 C7 -119.01(15) .
C1 C13 C12 C7 -0.50(16) .
C2 C1 C6 C5 -0.7(2) .
C13 C1 C6 C5 178.80(15) .
C2 C1 C6 C7 -179.95(15) .
C13 C1 C6 C7 -0.42(18) .
C11 C12 C7 C8 -0.9(2) .
C13 C12 C7 C8 -179.20(14) .
C11 C12 C7 C6 178.58(15) .
C13 C12 C7 C6 0.29(18) .
C5 C6 C7 C8 0.4(3) .
C1 C6 C7 C8 179.49(17) .
C5 C6 C7 C12 -179.02(17) .
C1 C6 C7 C12 0.08(18) .
C7 C12 C11 C10 0.1(3) .
C13 C12 C11 C10 178.03(16) .
C6 C1 C2 C3 -0.1(3) .
C13 C1 C2 C3 -179.57(16) .
C1 C6 C5 C4 0.9(3) .
C7 C6 C5 C4 179.91(17) .
C12 C11 C10 C9 0.8(3) .
C12 C7 C8 C9 0.8(3) .
C6 C7 C8 C9 -178.51(17) .
C1 C2 C3 C4 0.8(3) .
C6 C5 C4 C3 -0.2(3) .
C2 C3 C4 C5 -0.7(3) .
C7 C8 C9 C10 0.0(3) .
C11 C10 C9 C8 -0.9(3) .
