#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/08/2220844.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2220844
loop_
_publ_author_name
'Gu, Wei-Jin'
'Wang, Bing-Xiang'
_publ_section_title
;
 (Pyridine-2,6-diyldimethylene)bis(diphenylmethanol)
;
_journal_coeditor_code           IS2375
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o233
_journal_paper_doi               10.1107/S1600536808043572
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C33 H29 N O2'
_chemical_formula_moiety         'C33 H29 N O2'
_chemical_formula_sum            'C33 H29 N O2'
_chemical_formula_weight         471.57
_chemical_name_common            2,6-Bis(2-hydroxy-2,2-diphenylethyl)pyridine
_chemical_name_systematic
;
(Pyridine-2,6-diyldimethylene)bis(diphenylmethanol)
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 121.234(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.492(3)
_cell_length_b                   10.1039(17)
_cell_length_c                   16.097(3)
_cell_measurement_reflns_used    6093
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.39
_cell_volume                     2571.7(8)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10905
_diffrn_reflns_theta_full        27.60
_diffrn_reflns_theta_max         27.60
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.392
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         2960
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0543
_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)+(0.05P)²+1.99P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1269
_reflns_number_gt                2695
_reflns_number_total             2960
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2375.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2220844
_cod_database_fobs_code          2220844
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.3187(2) 0.9740(4) 0.4335(3) 0.0489(8) Uani d . 1 . .
C C2 0.2728(3) 0.9343(4) 0.4758(3) 0.0537(9) Uani d . 1 . .
H H2 0.2837 0.9721 0.5339 0.064 Uiso calc R 1 . .
C C3 0.2110(3) 0.8385(4) 0.4312(3) 0.0548(10) Uani d . 1 . .
H H3 0.1804 0.8102 0.4589 0.066 Uiso calc R 1 . .
C C4 0.1957(3) 0.7858(5) 0.3442(3) 0.0563(10) Uani d . 1 . .
H H4 0.1535 0.7228 0.3115 0.068 Uiso calc R 1 . .
C C5 0.2441(2) 0.8281(4) 0.3068(2) 0.0427(7) Uani d . 1 . .
C C6 0.3866(3) 1.0774(4) 0.4800(3) 0.0526(9) Uani d . 1 . .
H H6A 0.3791 1.1265 0.5269 0.063 Uiso calc R 1 . .
H H6B 0.3803 1.1391 0.4305 0.063 Uiso calc R 1 . .
C C7 0.4777(2) 1.0188(3) 0.5323(2) 0.0416(7) Uani d . 1 . .
C C8 0.5447(2) 1.1246(4) 0.5841(2) 0.0443(8) Uani d . 1 . .
C C9 0.5332(3) 1.2363(4) 0.6268(3) 0.0535(9) Uani d . 1 . .
H H9 0.4815 1.2498 0.6223 0.064 Uiso calc R 1 . .
C C10 0.5985(3) 1.3284(4) 0.6764(3) 0.0532(9) Uani d . 1 . .
H H10 0.5901 1.4024 0.7047 0.064 Uiso calc R 1 . .
C C11 0.6736(3) 1.3097(4) 0.6831(3) 0.0591(11) Uani d . 1 . .
H H11 0.7171 1.3705 0.7169 0.071 Uiso calc R 1 . .
C C12 0.6865(3) 1.2012(4) 0.6403(3) 0.0581(11) Uani d . 1 . .
H H12 0.7380 1.1906 0.6439 0.070 Uiso calc R 1 . .
C C13 0.6231(3) 1.1077(4) 0.5919(3) 0.0542(9) Uani d . 1 . .
H H13 0.6327 1.0338 0.5645 0.065 Uiso calc R 1 . .
C C14 0.4830(2) 0.9113(4) 0.6037(3) 0.0428(7) Uani d . 1 . .
C C15 0.4833(3) 0.9465(4) 0.6872(3) 0.0518(9) Uani d . 1 . .
H H15 0.4867 1.0353 0.7039 0.062 Uiso calc R 1 . .
C C16 0.4785(3) 0.8508(4) 0.7464(3) 0.0547(10) Uani d . 1 . .
H H16 0.4777 0.8753 0.8016 0.066 Uiso calc R 1 . .
C C17 0.4751(3) 0.7177(4) 0.7218(3) 0.0584(11) Uani d . 1 . .
H H17 0.4713 0.6525 0.7601 0.070 Uiso calc R 1 . .
C C18 0.4773(3) 0.6844(4) 0.6424(3) 0.0603(10) Uani d . 1 . .
H H18 0.4763 0.5953 0.6275 0.072 Uiso calc R 1 . .
C C19 0.4810(3) 0.7780(4) 0.5822(3) 0.0574(10) Uani d . 1 . .
H H19 0.4823 0.7518 0.5275 0.069 Uiso calc R 1 . .
C C20 0.2248(2) 0.7717(4) 0.2092(3) 0.0482(8) Uani d . 1 . .
H H20A 0.1883 0.8332 0.1582 0.058 Uiso calc R 1 . .
H H20B 0.1938 0.6895 0.1974 0.058 Uiso calc R 1 . .
C C21 0.3036(2) 0.7445(3) 0.2015(2) 0.0392(7) Uani d . 1 . .
C C22 0.2752(2) 0.6821(4) 0.1024(2) 0.0410(7) Uani d . 1 . .
C C23 0.3043(3) 0.5634(4) 0.0909(3) 0.0542(10) Uani d . 1 . .
H H23 0.3442 0.5168 0.1454 0.065 Uiso calc R 1 . .
C C24 0.2749(3) 0.5108(5) -0.0018(3) 0.0609(11) Uani d . 1 . .
H H24 0.2961 0.4306 -0.0084 0.073 Uiso calc R 1 . .
C C25 0.2159(3) 0.5761(4) -0.0816(3) 0.0561(10) Uani d . 1 . .
H H25 0.1949 0.5396 -0.1430 0.067 Uiso calc R 1 . .
C C26 0.1877(3) 0.6941(5) -0.0720(3) 0.0631(12) Uani d . 1 . .
H H26 0.1476 0.7396 -0.1271 0.076 Uiso calc R 1 . .
C C27 0.2175(3) 0.7490(4) 0.0192(3) 0.0602(11) Uani d . 1 . .
H H27 0.1985 0.8320 0.0243 0.072 Uiso calc R 1 . .
C C28 0.3695(2) 0.6555(3) 0.2848(2) 0.0383(7) Uani d . 1 . .
C C29 0.4551(2) 0.6722(4) 0.3192(3) 0.0573(10) Uani d . 1 . .
H H29 0.4729 0.7406 0.2954 0.069 Uiso calc R 1 . .
C C30 0.5141(3) 0.5866(4) 0.3892(3) 0.0618(11) Uani d . 1 . .
H H30 0.5714 0.5978 0.4123 0.074 Uiso calc R 1 . .
C C31 0.4874(3) 0.4844(4) 0.4249(3) 0.0521(10) Uani d . 1 . .
H H31 0.5269 0.4271 0.4717 0.063 Uiso calc R 1 . .
C C32 0.4018(3) 0.4677(5) 0.3905(3) 0.0618(12) Uani d . 1 . .
H H32 0.3840 0.3992 0.4143 0.074 Uiso calc R 1 . .
C C33 0.3429(2) 0.5532(4) 0.3204(3) 0.0470(9) Uani d . 1 . .
H H33 0.2856 0.5421 0.2974 0.056 Uiso calc R 1 . .
N N1 0.3029(2) 0.9203(3) 0.3487(2) 0.0467(7) Uani d . 1 . .
O O1 0.49165(17) 0.9616(3) 0.46054(19) 0.0497(6) Uani d . 1 . .
H H1 0.451(3) 0.917(5) 0.423(4) 0.060 Uiso d . 1 . .
O O2 0.34180(18) 0.8688(3) 0.2017(2) 0.0503(6) Uani d . 1 . .
H H2A 0.352(3) 0.911(5) 0.250(4) 0.060 Uiso d . 1 . .
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 120.6(4) ?
N1 C1 C6 . . 118.0(4) ?
C2 C1 C6 . . 121.4(4) ?
C3 C2 C1 . . 119.8(4) ?
C3 C2 H2 . . 120.1 ?
C1 C2 H2 . . 120.1 ?
C2 C3 C4 . . 118.4(4) ?
C2 C3 H3 . . 120.8 ?
C4 C3 H3 . . 120.8 ?
C5 C4 C3 . . 118.9(4) ?
C5 C4 H4 . . 120.5 ?
C3 C4 H4 . . 120.5 ?
N1 C5 C4 . . 122.9(4) ?
N1 C5 C20 . . 118.7(3) ?
C4 C5 C20 . . 118.3(4) ?
C1 C6 C7 . . 113.3(3) ?
C1 C6 H6A . . 108.9 ?
C7 C6 H6A . . 108.9 ?
C1 C6 H6B . . 108.9 ?
C7 C6 H6B . . 108.9 ?
H6A C6 H6B . . 107.7 ?
O1 C7 C8 . . 106.9(3) ?
O1 C7 C14 . . 110.4(3) ?
C8 C7 C14 . . 111.6(3) ?
O1 C7 C6 . . 108.3(3) ?
C8 C7 C6 . . 112.1(3) ?
C14 C7 C6 . . 107.6(3) ?
C9 C8 C13 . . 118.1(4) ?
C9 C8 C7 . . 123.4(3) ?
C13 C8 C7 . . 118.4(3) ?
C8 C9 C10 . . 120.8(4) ?
C8 C9 H9 . . 119.6 ?
C10 C9 H9 . . 119.6 ?
C11 C10 C9 . . 120.0(4) ?
C11 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
C10 C11 C12 . . 120.5(4) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C11 C12 C13 . . 120.5(4) ?
C11 C12 H12 . . 119.7 ?
C13 C12 H12 . . 119.7 ?
C12 C13 C8 . . 120.0(4) ?
C12 C13 H13 . . 120.0 ?
C8 C13 H13 . . 120.0 ?
C19 C14 C15 . . 118.6(4) ?
C19 C14 C7 . . 120.8(3) ?
C15 C14 C7 . . 120.5(3) ?
C14 C15 C16 . . 121.0(4) ?
C14 C15 H15 . . 119.5 ?
C16 C15 H15 . . 119.5 ?
C15 C16 C17 . . 119.0(4) ?
C15 C16 H16 . . 120.5 ?
C17 C16 H16 . . 120.5 ?
C18 C17 C16 . . 119.6(3) ?
C18 C17 H17 . . 120.2 ?
C16 C17 H17 . . 120.2 ?
C17 C18 C19 . . 122.3(4) ?
C17 C18 H18 . . 118.9 ?
C19 C18 H18 . . 118.9 ?
C18 C19 C14 . . 119.5(4) ?
C18 C19 H19 . . 120.2 ?
C14 C19 H19 . . 120.2 ?
C5 C20 C21 . . 114.8(3) ?
C5 C20 H20A . . 108.6 ?
C21 C20 H20A . . 108.6 ?
C5 C20 H20B . . 108.6 ?
C21 C20 H20B . . 108.6 ?
H20A C20 H20B . . 107.5 ?
O2 C21 C22 . . 105.3(3) ?
O2 C21 C28 . . 109.9(3) ?
C22 C21 C28 . . 110.7(3) ?
O2 C21 C20 . . 109.0(3) ?
C22 C21 C20 . . 109.0(3) ?
C28 C21 C20 . . 112.6(3) ?
C23 C22 C27 . . 117.3(4) ?
C23 C22 C21 . . 123.8(3) ?
C27 C22 C21 . . 119.0(3) ?
C22 C23 C24 . . 121.0(4) ?
C22 C23 H23 . . 119.5 ?
C24 C23 H23 . . 119.5 ?
C25 C24 C23 . . 120.3(4) ?
C25 C24 H24 . . 119.9 ?
C23 C24 H24 . . 119.9 ?
C26 C25 C24 . . 119.7(4) ?
C26 C25 H25 . . 120.2 ?
C24 C25 H25 . . 120.2 ?
C25 C26 C27 . . 120.8(4) ?
C25 C26 H26 . . 119.6 ?
C27 C26 H26 . . 119.6 ?
C22 C27 C26 . . 120.9(4) ?
C22 C27 H27 . . 119.5 ?
C26 C27 H27 . . 119.5 ?
C29 C28 C33 . . 120.0(3) ?
C29 C28 C21 . . 119.8(3) ?
C33 C28 C21 . . 120.1(3) ?
C28 C29 C30 . . 120.0(4) ?
C28 C29 H29 . . 120.0 ?
C30 C29 H29 . . 120.0 ?
C31 C30 C29 . . 120.0(4) ?
C31 C30 H30 . . 120.0 ?
C29 C30 H30 . . 120.0 ?
C30 C31 C32 . . 120.0(3) ?
C30 C31 H31 . . 120.0 ?
C32 C31 H31 . . 120.0 ?
C33 C32 C31 . . 120.0(4) ?
C33 C32 H32 . . 120.0 ?
C31 C32 H32 . . 120.0 ?
C32 C33 C28 . . 120.0(3) ?
C32 C33 H33 . . 120.0 ?
C28 C33 H33 . . 120.0 ?
C5 N1 C1 . . 119.2(3) n
C7 O1 H1 . . 109(3) n
C21 O2 H2A . . 109(3) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.353(5) n
C1 C2 . 1.394(6) ?
C1 C6 . 1.501(6) ?
C2 C3 . 1.381(6) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.384(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.381(5) ?
C4 H4 . 0.9300 ?
C5 N1 . 1.321(5) n
C5 C20 . 1.530(5) ?
C6 C7 . 1.557(5) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 O1 . 1.431(4) n
C7 C8 . 1.518(5) ?
C7 C14 . 1.547(5) ?
C8 C9 . 1.394(5) ?
C8 C13 . 1.399(6) ?
C9 C10 . 1.401(6) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.350(6) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.380(6) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.388(5) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 C19 . 1.387(5) ?
C14 C15 . 1.387(5) ?
C15 C16 . 1.392(5) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.394(6) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.342(7) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.382(6) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
C20 C21 . 1.549(5) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C21 O2 . 1.440(4) n
C21 C22 . 1.533(5) ?
C21 C28 . 1.548(5) ?
C22 C23 . 1.366(5) ?
C22 C27 . 1.381(5) ?
C23 C24 . 1.401(5) ?
C23 H23 . 0.9300 ?
C24 C25 . 1.351(6) ?
C24 H24 . 0.9300 ?
C25 C26 . 1.342(5) ?
C25 H25 . 0.9300 ?
C26 C27 . 1.388(6) ?
C26 H26 . 0.9300 ?
C27 H27 . 0.9300 ?
C28 C29 . 1.390(5) ?
C28 C33 . 1.390(4) ?
C29 C30 . 1.390(6) ?
C29 H29 . 0.9300 ?
C30 C31 . 1.390(6) ?
C30 H30 . 0.9300 ?
C31 C32 . 1.390(6) ?
C31 H31 . 0.9300 ?
C32 C33 . 1.390(5) ?
C32 H32 . 0.9300 ?
C33 H33 . 0.9300 ?
O1 H1 . 0.82(5) n
O2 H2A . 0.82(5) n
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N1 . 0.82(5) 2.34(5) 3.013(4) 139(4) y
O2 H2A N1 . 0.82(5) 2.20(5) 2.854(4) 136(4) y
C31 H31 Cg1 1_545 0.93 3.08 3.973(3) 162 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9629087
