#------------------------------------------------------------------------------
#$Date: 2016-03-26 23:02:33 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180527 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/96/7219669.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_7219669
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
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                90.00
_cell_angle_beta                 108.4400(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.1858(2)
_cell_length_b                   11.5886(2)
_cell_length_c                   12.1497(2)
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      36.17
_cell_measurement_theta_min      2.49
_cell_volume                     1093.37(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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0090
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26372
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9861
_exptl_absorpt_correction_T_min  0.9658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DMSO'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0409
_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)+(0.0531P)²+0.7057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1087
_reflns_number_gt                1807
_reflns_number_total             1925
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c5ce00180c3.cif
_cod_data_source_block           feka_38_monop
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      'P21/c  '
_cod_database_code               7219669
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.05625(18) 0.40728(12) 0.38885(12) 0.0274(3) Uani 1 1 d .
N2 N -0.23900(17) 0.67172(13) 0.22298(12) 0.0284(3) Uani 1 1 d .
O1 O -0.19001(15) 0.36292(9) 0.20069(10) 0.0277(3) Uani 1 1 d .
H1 H -0.1361 0.3310 0.2616 0.042 Uiso 1 1 calc R
C1 C 0.02527(19) 0.49470(13) 0.31179(13) 0.0196(3) Uani 1 1 d .
C2 C 0.1238(2) 0.59248(14) 0.32960(14) 0.0242(4) Uani 1 1 d .
H2 H 0.1002 0.6510 0.2744 0.029 Uiso 1 1 calc R
C3 C 0.2592(2) 0.60210(16) 0.43146(16) 0.0328(4) Uani 1 1 d .
H3 H 0.3274 0.6681 0.4460 0.039 Uiso 1 1 calc R
C4 C 0.2932(2) 0.51392(16) 0.51164(15) 0.0306(4) Uani 1 1 d .
H4 H 0.3843 0.5194 0.5805 0.037 Uiso 1 1 calc R
C5 C 0.1900(2) 0.41782(15) 0.48774(14) 0.0289(4) Uani 1 1 d .
H5 H 0.2129 0.3579 0.5414 0.035 Uiso 1 1 calc R
C6 C -0.27630(18) 0.56055(13) 0.19476(12) 0.0193(3) Uani 1 1 d .
C7 C -0.44158(18) 0.51825(14) 0.16081(12) 0.0208(3) Uani 1 1 d .
H7 H -0.4629 0.4410 0.1405 0.025 Uiso 1 1 calc R
C8 C -0.5744(2) 0.59150(16) 0.15724(14) 0.0303(4) Uani 1 1 d .
H8 H -0.6868 0.5640 0.1354 0.036 Uiso 1 1 calc R
C9 C -0.5410(2) 0.70618(16) 0.18616(14) 0.0320(4) Uani 1 1 d .
H9 H -0.6298 0.7569 0.1847 0.038 Uiso 1 1 calc R
C10 C -0.3722(2) 0.74384(16) 0.21743(15) 0.0311(4) Uani 1 1 d .
H10 H -0.3490 0.8214 0.2353 0.037 Uiso 1 1 calc R
C11 C -0.12780(18) 0.47690(12) 0.20017(13) 0.0193(3) Uani 1 1 d .
C12 C -0.06813(19) 0.59547(13) 0.03768(13) 0.0202(3) Uani 1 1 d .
H12 H -0.1136 0.6603 0.0625 0.024 Uiso 1 1 calc R
C13 C -0.06410(17) 0.49095(12) 0.09436(12) 0.0169(3) Uani 1 1 d .
C14 C 0.00514(18) 0.39541(13) 0.05578(13) 0.0197(3) Uani 1 1 d .
H14 H 0.0094 0.3247 0.0928 0.024 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 118.11(14) . .
C6 N2 C10 117.61(14) . .
C11 O1 H1 109.5 . .
N1 C1 C2 122.73(15) . .
N1 C1 C11 115.62(13) . .
C2 C1 C11 121.64(13) . .
C1 C2 C3 118.36(15) . .
C1 C2 H2 120.8 . .
C3 C2 H2 120.8 . .
C4 C3 C2 119.97(16) . .
C4 C3 H3 120.0 . .
C2 C3 H3 120.0 . .
C5 C4 C3 118.61(16) . .
C5 C4 H4 120.7 . .
C3 C4 H4 120.7 . .
N1 C5 C4 122.22(15) . .
N1 C5 H5 118.9 . .
C4 C5 H5 118.9 . .
N2 C6 C7 122.79(14) . .
N2 C6 C11 118.70(13) . .
C7 C6 C11 118.51(13) . .
C8 C7 C6 119.01(15) . .
C8 C7 H7 120.5 . .
C6 C7 H7 120.5 . .
C7 C8 C9 119.87(15) . .
C7 C8 H8 120.1 . .
C9 C8 H8 120.1 . .
C8 C9 C10 118.30(15) . .
C8 C9 H9 120.9 . .
C10 C9 H9 120.9 . .
N2 C10 C9 122.41(16) . .
N2 C10 H10 118.8 . .
C9 C10 H10 118.8 . .
O1 C11 C6 107.89(11) . .
O1 C11 C13 108.62(11) . .
C6 C11 C13 111.63(12) . .
O1 C11 C1 108.31(12) . .
C6 C11 C1 111.36(12) . .
C13 C11 C1 108.93(11) . .
C13 C12 C14 120.94(14) . 3_565
C13 C12 H12 119.5 . .
C14 C12 H12 119.5 3_565 .
C12 C13 C14 118.39(13) . .
C12 C13 C11 123.00(13) . .
C14 C13 C11 118.58(13) . .
C13 C14 C12 120.67(14) . 3_565
C13 C14 H14 119.7 . .
C12 C14 H14 119.7 3_565 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.348(2) .
N1 C5 1.351(2) .
N2 C6 1.343(2) .
N2 C10 1.358(2) .
O1 C11 1.4164(17) .
O1 H1 0.8200 .
C1 C2 1.368(2) .
C1 C11 1.542(2) .
C2 C3 1.380(2) .
C2 H2 0.9300 .
C3 C4 1.378(3) .
C3 H3 0.9300 .
C4 C5 1.372(3) .
C4 H4 0.9300 .
C5 H5 0.9300 .
C6 C7 1.374(2) .
C6 C11 1.540(2) .
C7 C8 1.369(2) .
C7 H7 0.9300 .
C8 C9 1.380(3) .
C8 H8 0.9300 .
C9 C10 1.383(3) .
C9 H9 0.9300 .
C10 H10 0.9300 .
C11 C13 1.541(2) .
C12 C13 1.388(2) .
C12 C14 1.392(2) 3_565
C12 H12 0.9300 .
C13 C14 1.391(2) .
C14 C12 1.392(2) 3_565
C14 H14 0.9300 .
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 0.82 2.03 2.5765(18) 123.9 .
C2 H2 O1 0.93 2.55 3.2214(19) 129.0 2
C9 H9 O1 0.93 2.63 3.4572(19) 148.2 2_455
C12 H12 N2 0.93 2.48 3.130(2) 127.3 .
C8 H8 Cg3 0.93 2.68 3.5640(16) 160.0 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 0.3(2) . .
C5 N1 C1 C11 179.35(13) . .
N1 C1 C2 C3 -0.8(2) . .
C11 C1 C2 C3 -179.74(13) . .
C1 C2 C3 C4 0.7(2) . .
C2 C3 C4 C5 -0.1(2) . .
C1 N1 C5 C4 0.2(2) . .
C3 C4 C5 N1 -0.3(2) . .
C10 N2 C6 C7 0.2(2) . .
C10 N2 C6 C11 179.93(13) . .
N2 C6 C7 C8 -1.1(2) . .
C11 C6 C7 C8 179.10(13) . .
C6 C7 C8 C9 0.8(2) . .
C7 C8 C9 C10 0.4(2) . .
C6 N2 C10 C9 1.2(2) . .
C8 C9 C10 N2 -1.5(2) . .
N2 C6 C11 O1 163.13(13) . .
C7 C6 C11 O1 -17.11(18) . .
N2 C6 C11 C13 -77.60(16) . .
C7 C6 C11 C13 102.16(15) . .
N2 C6 C11 C1 44.39(17) . .
C7 C6 C11 C1 -135.84(14) . .
N1 C1 C11 O1 -6.24(17) . .
C2 C1 C11 O1 172.79(13) . .
N1 C1 C11 C6 112.24(14) . .
C2 C1 C11 C6 -68.73(17) . .
N1 C1 C11 C13 -124.21(13) . .
C2 C1 C11 C13 54.82(18) . .
C14 C12 C13 C14 0.2(2) 3_565 .
C14 C12 C13 C11 178.37(13) 3_565 .
O1 C11 C13 C12 150.20(13) . .
C6 C11 C13 C12 31.36(19) . .
C1 C11 C13 C12 -92.03(16) . .
O1 C11 C13 C14 -31.69(17) . .
C6 C11 C13 C14 -150.52(13) . .
C1 C11 C13 C14 86.09(15) . .
C12 C13 C14 C12 -0.2(2) . 3_565
C11 C13 C14 C12 -178.45(13) . 3_565
