#------------------------------------------------------------------------------
#$Date: 2016-03-26 23:02:33 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180527 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/96/7219671.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_7219671
loop_
_publ_author_name
'Katzsch, Felix'
'Weber, Edwin'
_publ_section_title
;
 Crystalline inclusion properties of new pyridine and thiophene modified
 wheel-and-axle diol hosts
;
_journal_issue                   13
_journal_name_full               CrystEngComm
_journal_page_first              2737
_journal_paper_doi               10.1039/C5CE00180C
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C28 H22 N4 O2'
_chemical_formula_sum            'C28 H22 N4 O2'
_chemical_formula_weight         446.50
_chemical_name_systematic        1,4-Bis[di(pyrid-2-yl)hydroxymethyl]benzene
_chemical_properties_physical    'Air-sensitive, Heat-sensitive'
_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
;
2014-08-22 deposited with the CCDC.
2015-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                106.597(2)
_cell_angle_beta                 108.7020(10)
_cell_angle_gamma                100.101(2)
_cell_formula_units_Z            1
_cell_length_a                   8.1184(2)
_cell_length_b                   9.9587(3)
_cell_length_c                   10.9050(3)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.02
_cell_measurement_theta_min      2.45
_cell_volume                     764.91(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ 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  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0150
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16345
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_correction_T_min  0.9528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.969
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             234
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene'
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_platon_squeeze_details
;
;
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0421
_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)+(0.0766P)²+0.1732P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1237
_reflns_number_gt                2453
_reflns_number_total             2694
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c5ce00180c3.cif
_cod_data_source_block           feka_46_p-1_neu
_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 3086 2015-02-26 13:12:21Z robertas 

 Adding full bibliography for 7219669--7219676.cif.
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               7219671
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
N1 N 0.27592(14) 0.97152(12) 0.35946(11) 0.0225(3) Uani 1 1 d .
N2 N 0.25001(15) 0.63534(12) 0.08626(12) 0.0287(3) Uani 1 1 d .
O1 O 0.58698(10) 0.97450(9) 0.33589(8) 0.0189(2) Uani 1 1 d .
H1 H 0.5558 0.9844 0.4036 0.028 Uiso 1 1 calc R
C1 C 0.26129(15) 0.92396(12) 0.22812(12) 0.0166(3) Uani 1 1 d .
C2 C 0.10300(16) 0.90277(13) 0.11649(12) 0.0208(3) Uani 1 1 d .
H2 H 0.0965 0.8678 0.0239 0.025 Uiso 1 1 calc R
C3 C -0.04467(16) 0.93345(13) 0.14261(13) 0.0216(3) Uani 1 1 d .
H3 H -0.1543 0.9201 0.0681 0.026 Uiso 1 1 calc R
C4 C -0.03083(17) 0.98382(14) 0.27853(13) 0.0239(3) Uani 1 1 d .
H4 H -0.1301 1.0060 0.2996 0.029 Uiso 1 1 calc R
C5 C 0.13109(18) 1.00100(16) 0.38276(13) 0.0283(3) Uani 1 1 d .
H5 H 0.1407 1.0356 0.4762 0.034 Uiso 1 1 calc R
C6 C 0.41285(16) 0.72807(13) 0.17471(12) 0.0185(3) Uani 1 1 d .
C7 C 0.55870(19) 0.68061(16) 0.23184(16) 0.0339(3) Uani 1 1 d .
H7 H 0.6741 0.7491 0.2930 0.041 Uiso 1 1 calc R
C8 C 0.5342(2) 0.53203(17) 0.19870(18) 0.0430(4) Uani 1 1 d .
H8 H 0.6326 0.4969 0.2369 0.052 Uiso 1 1 calc R
C9 C 0.36649(19) 0.43575(15) 0.11018(16) 0.0323(3) Uani 1 1 d .
H9 H 0.3456 0.3331 0.0872 0.039 Uiso 1 1 calc R
C10 C 0.22946(19) 0.49167(15) 0.05562(16) 0.0328(3) Uani 1 1 d .
H10 H 0.1138 0.4248 -0.0073 0.039 Uiso 1 1 calc R
C11 C 0.43313(15) 0.89295(13) 0.21002(11) 0.0164(3) Uani 1 1 d .
C12 C 0.41537(16) 0.85274(13) -0.03812(12) 0.0190(3) Uani 1 1 d .
H12 H 0.3567 0.7514 -0.0655 0.023 Uiso 1 1 calc R
C13 C 0.46704(14) 0.94567(12) 0.09855(12) 0.0156(3) Uani 1 1 d .
C14 C 0.55174(16) 1.09407(13) 0.13538(12) 0.0188(3) Uani 1 1 d .
H14 H 0.5874 1.1596 0.2282 0.023 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
C1 N1 C5 117.68(10) . .
C6 N2 C10 117.70(11) . .
C11 O1 H1 109.5 . .
N1 C1 C2 122.60(11) . .
N1 C1 C11 114.56(10) . .
C2 C1 C11 122.84(10) . .
C3 C2 C1 118.84(11) . .
C3 C2 H2 120.6 . .
C1 C2 H2 120.6 . .
C2 C3 C4 119.13(11) . .
C2 C3 H3 120.4 . .
C4 C3 H3 120.4 . .
C5 C4 C3 118.12(11) . .
C5 C4 H4 120.9 . .
C3 C4 H4 120.9 . .
N1 C5 C4 123.63(11) . .
N1 C5 H5 118.2 . .
C4 C5 H5 118.2 . .
N2 C6 C7 122.32(12) . .
N2 C6 C11 116.92(10) . .
C7 C6 C11 120.76(11) . .
C8 C7 C6 118.91(13) . .
C8 C7 H7 120.5 . .
C6 C7 H7 120.5 . .
C9 C8 C7 119.31(13) . .
C9 C8 H8 120.3 . .
C7 C8 H8 120.3 . .
C8 C9 C10 118.18(13) . .
C8 C9 H9 120.9 . .
C10 C9 H9 120.9 . .
N2 C10 C9 123.56(13) . .
N2 C10 H10 118.2 . .
C9 C10 H10 118.2 . .
O1 C11 C13 106.28(8) . .
O1 C11 C1 109.28(9) . .
C13 C11 C1 110.59(9) . .
O1 C11 C6 109.37(9) . .
C13 C11 C6 112.03(9) . .
C1 C11 C6 109.22(9) . .
C13 C12 C14 120.90(11) . 2_675
C13 C12 H12 119.5 . .
C14 C12 H12 119.5 2_675 .
C12 C13 C14 118.24(11) . .
C12 C13 C11 123.08(10) . .
C14 C13 C11 118.68(10) . .
C12 C14 C13 120.86(11) 2_675 .
C12 C14 H14 119.6 2_675 .
C13 C14 H14 119.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.3317(16) .
N1 C5 1.3428(16) .
N2 C6 1.3327(16) .
N2 C10 1.3394(18) .
O1 C11 1.4183(13) .
O1 H1 0.8400 .
C1 C2 1.3903(17) .
C1 C11 1.5405(15) .
C2 C3 1.3818(17) .
C2 H2 0.9500 .
C3 C4 1.3819(18) .
C3 H3 0.9500 .
C4 C5 1.3788(18) .
C4 H4 0.9500 .
C5 H5 0.9500 .
C6 C7 1.3802(18) .
C6 C11 1.5411(16) .
C7 C8 1.380(2) .
C7 H7 0.9500 .
C8 C9 1.369(2) .
C8 H8 0.9500 .
C9 C10 1.372(2) .
C9 H9 0.9500 .
C10 H10 0.9500 .
C11 C13 1.5355(15) .
C12 C13 1.3888(16) .
C12 C14 1.3892(17) 2_675
C12 H12 0.9500 .
C13 C14 1.3948(17) .
C14 C12 1.3892(17) 2_675
C14 H14 0.9500 .
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
O1 H1 N1 0.84 2.14 2.6150(13) 115.8 .
O1 H1 N1 0.84 2.37 2.9939(13) 131.6 2_676
C4 H4 O1 0.95 2.44 3.3472(14) 160.7 1_455
C5 H5 O1 0.95 2.53 3.0959(15) 118.6 2_676
C10 H10 N2 0.95 2.70 3.5267(17) 146.2 2_565
C12 H12 N2 0.95 2.55 3.1867(16) 124.9 .
C3 H3 Cg3 0.95 2.97 3.7794(12) 143.3 1_455
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
C5 N1 C1 C2 -0.73(18) . .
C5 N1 C1 C11 179.86(11) . .
N1 C1 C2 C3 0.61(18) . .
C11 C1 C2 C3 179.97(10) . .
C1 C2 C3 C4 -0.15(18) . .
C2 C3 C4 C5 -0.14(19) . .
C1 N1 C5 C4 0.4(2) . .
C3 C4 C5 N1 0.0(2) . .
C10 N2 C6 C7 1.44(19) . .
C10 N2 C6 C11 -179.28(11) . .
N2 C6 C7 C8 -1.5(2) . .
C11 C6 C7 C8 179.28(13) . .
C6 C7 C8 C9 0.1(2) . .
C7 C8 C9 C10 1.2(2) . .
C6 N2 C10 C9 0.0(2) . .
C8 C9 C10 N2 -1.3(2) . .
N1 C1 C11 O1 -22.90(13) . .
C2 C1 C11 O1 157.69(10) . .
N1 C1 C11 C13 -139.56(10) . .
C2 C1 C11 C13 41.03(15) . .
N1 C1 C11 C6 96.71(12) . .
C2 C1 C11 C6 -82.70(13) . .
N2 C6 C11 O1 160.29(10) . .
C7 C6 C11 O1 -20.41(15) . .
N2 C6 C11 C13 -82.14(12) . .
C7 C6 C11 C13 97.16(13) . .
N2 C6 C11 C1 40.73(13) . .
C7 C6 C11 C1 -139.97(12) . .
C14 C12 C13 C14 0.44(18) 2_675 .
C14 C12 C13 C11 179.66(10) 2_675 .
O1 C11 C13 C12 143.12(10) . .
C1 C11 C13 C12 -98.37(12) . .
C6 C11 C13 C12 23.72(14) . .
O1 C11 C13 C14 -37.66(13) . .
C1 C11 C13 C14 80.85(12) . .
C6 C11 C13 C14 -157.06(10) . .
C12 C13 C14 C12 -0.44(18) . 2_675
C11 C13 C14 C12 -179.69(10) . 2_675
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.015 0.500 0.500 284 49 ' '
