#------------------------------------------------------------------------------
#$Date: 2016-02-13 13:50:18 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/22/7222255.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_7222255
loop_
_publ_author_name
'Samipillai, Marivel'
'Batisai, Eustina'
'Nassimbeni, Luigi R.'
'Weber, Edwin'
_publ_section_title
;
 Separation of lutidines by enclathration
;
_journal_issue                   43
_journal_name_full               CrystEngComm
_journal_page_first              8332
_journal_paper_doi               10.1039/C5CE01637A
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C36 H22 O2, 2(C7 H9 N)'
_chemical_formula_sum            'C50 H40 N2 O2'
_chemical_formula_weight         700.84
_chemical_name_common
1,4-bis(2?-bis(2?-(9-Hyrdoxy-9-fluorenyl)ethynyl)benzene.2(3,4-Lutidine)
_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
_audit_update_record
;
2015-08-12 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                77.867(2)
_cell_angle_beta                 77.131(2)
_cell_angle_gamma                70.639(2)
_cell_formula_units_Z            1
_cell_length_a                   7.6847(3)
_cell_length_b                   10.8142(5)
_cell_length_c                   12.3664(5)
_cell_measurement_reflns_used    3354
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.89
_cell_volume                     934.78(7)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (2000)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    XSEED
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '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  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0440
_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       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7992
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.89
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             370
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4239
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0407
_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)+(0.0493P)²+0.1885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                3354
_reflns_number_total             4239
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce01637a2.cif
_cod_data_source_block           H3.2(3,4LUT)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/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 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7222248--7222255.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7222255
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
O14 O 0.32793(10) 0.30474(8) 0.25916(6) 0.0301(2) Uani 1 1 d D
N20 N 0.55057(14) 0.16248(11) 0.08776(10) 0.0437(3) Uani 1 1 d D
C1 C 0.5031(2) 0.24041(18) 0.60581(11) 0.0502(4) Uani 1 1 d .
H1 H 0.4558 0.2758 0.6743 0.060 Uiso 1 1 calc R
C2 C 0.6296(2) 0.11547(19) 0.60335(13) 0.0582(4) Uani 1 1 d .
H2 H 0.6683 0.0646 0.6711 0.070 Uiso 1 1 calc R
C3 C 0.7014(2) 0.06240(17) 0.50410(13) 0.0537(4) Uani 1 1 d .
H3 H 0.7879 -0.0240 0.5046 0.064 Uiso 1 1 calc R
C4 C 0.64710(18) 0.13552(14) 0.40364(11) 0.0406(3) Uani 1 1 d .
H4 H 0.6970 0.1006 0.3351 0.049 Uiso 1 1 calc R
C5 C 0.51923(16) 0.25976(13) 0.40617(9) 0.0310(3) Uani 1 1 d .
C6 C 0.44635(17) 0.31353(14) 0.50623(10) 0.0358(3) Uani 1 1 d .
C7 C 0.31425(17) 0.44533(14) 0.48219(10) 0.0352(3) Uani 1 1 d .
C8 C 0.30369(15) 0.47236(12) 0.36798(10) 0.0296(3) Uani 1 1 d .
C9 C 0.18433(17) 0.58828(13) 0.32249(11) 0.0357(3) Uani 1 1 d .
H9 H 0.1786 0.6058 0.2446 0.043 Uiso 1 1 calc R
C10 C 0.07195(19) 0.67949(14) 0.39358(13) 0.0455(3) Uani 1 1 d .
H10 H -0.0118 0.7598 0.3640 0.055 Uiso 1 1 calc R
C11 C 0.0822(2) 0.65334(16) 0.50690(13) 0.0504(4) Uani 1 1 d .
H11 H 0.0049 0.7162 0.5543 0.060 Uiso 1 1 calc R
C12 C 0.2026(2) 0.53774(16) 0.55226(12) 0.0460(4) Uani 1 1 d .
H12 H 0.2095 0.5213 0.6300 0.055 Uiso 1 1 calc R
C13 C 0.43438(15) 0.35673(12) 0.30866(9) 0.0266(2) Uani 1 1 d .
C15 C 0.58126(15) 0.39803(11) 0.22321(9) 0.0270(2) Uani 1 1 d .
C16 C 0.70179(15) 0.42943(11) 0.15513(9) 0.0254(2) Uani 1 1 d .
C17 C 0.85268(14) 0.46530(10) 0.07598(9) 0.0237(2) Uani 1 1 d .
C18 C 0.83678(14) 0.51085(11) -0.03693(9) 0.0248(2) Uani 1 1 d .
H18 H 0.7254 0.5181 -0.0623 0.030 Uiso 1 1 calc R
C19 C 0.98203(15) 0.54555(11) -0.11209(9) 0.0255(2) Uani 1 1 d .
H19 H 0.9694 0.5769 -0.1885 0.031 Uiso 1 1 calc R
C21 C 0.63018(18) 0.03348(14) 0.11776(12) 0.0395(3) Uani 1 1 d .
H21 H 0.6006 -0.0029 0.1940 0.047 Uiso 1 1 calc R
C22 C 0.75327(16) -0.05155(12) 0.04569(11) 0.0340(3) Uani 1 1 d .
C23 C 0.79480(16) 0.00142(12) -0.06629(11) 0.0325(3) Uani 1 1 d .
C24 C 0.71147(18) 0.13599(13) -0.09775(12) 0.0386(3) Uani 1 1 d .
H24 H 0.7366 0.1754 -0.1735 0.046 Uiso 1 1 calc R
C25 C 0.59249(18) 0.21222(14) -0.01925(13) 0.0426(3) Uani 1 1 d .
H25 H 0.5381 0.3041 -0.0425 0.051 Uiso 1 1 calc R
C26 C 0.83615(18) -0.19434(13) 0.09001(10) 0.0472(3) Uani 1 1 d .
H26A H 0.7961 -0.2093 0.1714 0.071 Uiso 1 1 calc R
H26B H 0.9729 -0.2175 0.0731 0.071 Uiso 1 1 calc R
H26C H 0.7937 -0.2497 0.0546 0.071 Uiso 1 1 calc R
H14 H 0.4088 0.2565 0.1998 0.070(5) Uiso 1 1 d RD
C27 C 0.92409(19) -0.08391(14) -0.15093(12) 0.0442(3) Uani 1 1 d .
H27C H 0.9470 -0.0279 -0.2227 0.066 Uiso 1 1 calc R
H27B H 0.8665 -0.1482 -0.1611 0.066 Uiso 1 1 calc R
H27A H 1.0430 -0.1312 -0.1241 0.066 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
C13 O14 H14 109.6 . .
C25 N20 C21 117.11(10) . .
C2 C1 C6 118.77(14) . .
C2 C1 H1 120.6 . .
C6 C1 H1 120.6 . .
C1 C2 C3 121.49(14) . .
C1 C2 H2 119.3 . .
C3 C2 H2 119.3 . .
C2 C3 C4 120.17(15) . .
C2 C3 H3 119.9 . .
C4 C3 H3 119.9 . .
C5 C4 C3 118.40(13) . .
C5 C4 H4 120.8 . .
C3 C4 H4 120.8 . .
C4 C5 C6 121.55(12) . .
C4 C5 C13 128.21(11) . .
C6 C5 C13 110.24(11) . .
C1 C6 C5 119.61(14) . .
C1 C6 C7 131.60(13) . .
C5 C6 C7 108.78(11) . .
C8 C7 C12 119.55(13) . .
C8 C7 C6 108.99(11) . .
C12 C7 C6 131.43(12) . .
C9 C8 C7 121.48(11) . .
C9 C8 C13 128.10(11) . .
C7 C8 C13 110.40(11) . .
C8 C9 C10 118.49(13) . .
C8 C9 H9 120.8 . .
C10 C9 H9 120.8 . .
C11 C10 C9 120.28(14) . .
C11 C10 H10 119.9 . .
C9 C10 H10 119.9 . .
C12 C11 C10 121.22(13) . .
C12 C11 H11 119.4 . .
C10 C11 H11 119.4 . .
C11 C12 C7 118.98(13) . .
C11 C12 H12 120.5 . .
C7 C12 H12 120.5 . .
O14 C13 C15 110.89(9) . .
O14 C13 C8 109.48(8) . .
C15 C13 C8 111.21(9) . .
O14 C13 C5 112.50(9) . .
C15 C13 C5 110.83(9) . .
C8 C13 C5 101.59(9) . .
C16 C15 C13 178.88(13) . .
C15 C16 C17 177.71(12) . .
C18 C17 C19 119.08(9) . 2_765
C18 C17 C16 121.03(10) . .
C19 C17 C16 119.89(10) 2_765 .
C19 C18 C17 120.58(10) . .
C19 C18 H18 119.7 . .
C17 C18 H18 119.7 . .
C18 C19 C17 120.34(10) . 2_765
C18 C19 H19 119.8 . .
C17 C19 H19 119.8 2_765 .
N20 C21 C22 124.71(13) . .
N20 C21 H21 117.6 . .
C22 C21 H21 117.6 . .
C21 C22 C23 117.65(12) . .
C21 C22 C26 119.67(12) . .
C23 C22 C26 122.68(11) . .
C24 C23 C22 117.69(11) . .
C24 C23 C27 120.98(12) . .
C22 C23 C27 121.33(12) . .
C25 C24 C23 120.12(13) . .
C25 C24 H24 119.9 . .
C23 C24 H24 119.9 . .
N20 C25 C24 122.72(13) . .
N20 C25 H25 118.6 . .
C24 C25 H25 118.6 . .
C22 C26 H26A 109.5 . .
C22 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C22 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C23 C27 H27C 109.5 . .
C23 C27 H27B 109.5 . .
H27C C27 H27B 109.5 . .
C23 C27 H27A 109.5 . .
H27C C27 H27A 109.5 . .
H27B C27 H27A 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O14 C13 1.4257(13) .
O14 H14 0.9699 .
N20 C25 1.3305(18) .
N20 C21 1.3325(18) .
C1 C2 1.380(2) .
C1 C6 1.3904(19) .
C1 H1 0.9500 .
C2 C3 1.387(2) .
C2 H2 0.9500 .
C3 C4 1.3936(19) .
C3 H3 0.9500 .
C4 C5 1.3786(19) .
C4 H4 0.9500 .
C5 C6 1.4003(17) .
C5 C13 1.5310(16) .
C6 C7 1.465(2) .
C7 C8 1.3960(17) .
C7 C12 1.3964(18) .
C8 C9 1.3785(18) .
C8 C13 1.5281(16) .
C9 C10 1.3975(18) .
C9 H9 0.9500 .
C10 C11 1.385(2) .
C10 H10 0.9500 .
C11 C12 1.380(2) .
C11 H11 0.9500 .
C12 H12 0.9500 .
C13 C15 1.4814(15) .
C15 C16 1.1930(15) .
C16 C17 1.4443(14) .
C17 C18 1.3978(15) .
C17 C19 1.3994(15) 2_765
C18 C19 1.3855(15) .
C18 H18 0.9500 .
C19 C17 1.3994(15) 2_765
C19 H19 0.9500 .
C21 C22 1.3881(17) .
C21 H21 0.9500 .
C22 C23 1.3924(18) .
C22 C26 1.4960(18) .
C23 C24 1.3908(18) .
C23 C27 1.5063(17) .
C24 C25 1.3781(19) .
C24 H24 0.9500 .
C25 H25 0.9500 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C27 H27C 0.9800 .
C27 H27B 0.9800 .
C27 H27A 0.9800 .
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
O14 H14 N20 0.97 1.82 2.7923(10) 176.9
