#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/49/4504999.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_4504999
loop_
_publ_author_name
'Biradha, Kumar'
'Mahata, Goutam'
_publ_section_title
;
 Enclathration of Aromatic Molecules by the
 O−H···N Supramolecular Adducts of
 Racemic-bis-β-naphthol and 4,4‘-Bipyridine
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              61
_journal_paper_doi               10.1021/cg049761u
_journal_volume                  5
_journal_year                    2005
_chemical_formula_sum            'C36 H27 N2 O2'
_chemical_formula_weight         519.60
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 93.33(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.218(3)
_cell_length_b                   9.5360(19)
_cell_length_c                   17.675(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      7
_cell_volume                     2728.9(10)
_computing_cell_refinement       CAD4
_computing_data_collection       CAD4
_computing_data_reduction        MACH3
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  CAD4-MACH3
_diffrn_measurement_method       /w-scan
_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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0542
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4976
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.26
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Dirty-white
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'hexagonal flakes'
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.0036(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         4796
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.1267
_refine_ls_R_factor_gt           0.0575
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0542P)²+2.0310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1862
_reflns_number_gt                2681
_reflns_number_total             4796
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg049761usi20040712_065649.cif
_cod_data_source_block           2
_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.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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_cell_volume        2728.9(9)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4504999
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
O21 O 0.77207(16) 0.9256(3) 0.20368(14) 0.0629(7) Uani 1 1 d .
H21O H 0.766(3) 0.887(5) 0.248(2) 0.100(16) Uiso 1 1 d .
O31 O 0.61456(15) 1.1611(3) 0.24229(12) 0.0694(8) Uani 1 1 d .
H31O H 0.560(3) 1.164(6) 0.257(3) 0.15(2) Uiso 1 1 d .
N11 N 0.53468(18) 0.6580(4) 0.19224(17) 0.0675(8) Uani 1 1 d .
N10 N 0.7390(2) 0.6592(3) -0.15189(17) 0.0732(9) Uani 1 1 d .
C10 C 0.7210(3) 0.5411(4) -0.1166(2) 0.0884(14) Uani 1 1 d .
H10 H 0.7328 0.4564 -0.1397 0.106 Uiso 1 1 calc R
C11 C 0.6858(3) 0.5374(4) -0.0477(2) 0.0776(12) Uani 1 1 d .
H11 H 0.6764 0.4514 -0.0249 0.093 Uiso 1 1 calc R
C12 C 0.66469(19) 0.6585(3) -0.01239(17) 0.0496(8) Uani 1 1 d .
C13 C 0.6838(2) 0.7817(4) -0.0487(2) 0.0672(10) Uani 1 1 d .
H13 H 0.6721 0.8676 -0.0268 0.081 Uiso 1 1 calc R
C14 C 0.7202(3) 0.7775(4) -0.1175(2) 0.0745(11) Uani 1 1 d .
H14 H 0.7322 0.8620 -0.1408 0.089 Uiso 1 1 calc R
C15 C 0.5313(2) 0.5493(4) 0.1445(2) 0.0684(10) Uani 1 1 d .
H15 H 0.4989 0.4727 0.1562 0.082 Uiso 1 1 calc R
C16 C 0.5735(2) 0.5444(4) 0.07901(19) 0.0586(9) Uani 1 1 d .
H16 H 0.5692 0.4659 0.0478 0.070 Uiso 1 1 calc R
C17 C 0.62213(18) 0.6571(3) 0.05993(17) 0.0474(7) Uani 1 1 d .
C18 C 0.6270(2) 0.7681(4) 0.11022(18) 0.0554(8) Uani 1 1 d .
H18 H 0.6596 0.8455 0.1004 0.066 Uiso 1 1 calc R
C19 C 0.5837(2) 0.7642(4) 0.17488(19) 0.0630(9) Uani 1 1 d .
H19 H 0.5889 0.8396 0.2082 0.076 Uiso 1 1 calc R
C20 C 0.77134(17) 1.1728(3) 0.18710(15) 0.0413(7) Uani 1 1 d .
C21 C 0.80683(18) 1.0547(3) 0.21952(16) 0.0468(7) Uani 1 1 d .
C22 C 0.87782(19) 1.0623(4) 0.26945(17) 0.0557(9) Uani 1 1 d .
H22 H 0.9012 0.9809 0.2903 0.067 Uiso 1 1 calc R
C23 C 0.91182(19) 1.1899(4) 0.28694(18) 0.0576(9) Uani 1 1 d .
H23 H 0.9586 1.1945 0.3199 0.069 Uiso 1 1 calc R
C24 C 0.9102(2) 1.4484(4) 0.27538(19) 0.0623(10) Uani 1 1 d .
H24 H 0.9573 1.4548 0.3079 0.075 Uiso 1 1 calc R
C25 C 0.8744(2) 1.5683(4) 0.2475(2) 0.0689(10) Uani 1 1 d .
H25 H 0.8964 1.6552 0.2615 0.083 Uiso 1 1 calc R
C26 C 0.8047(2) 1.5597(4) 0.1980(2) 0.0642(9) Uani 1 1 d .
H26 H 0.7803 1.6416 0.1788 0.077 Uiso 1 1 calc R
C27 C 0.7716(2) 1.4330(3) 0.17713(18) 0.0522(8) Uani 1 1 d .
H27 H 0.7251 1.4299 0.1437 0.063 Uiso 1 1 calc R
C28 C 0.80656(17) 1.3061(3) 0.20543(15) 0.0440(7) Uani 1 1 d .
C29 C 0.87787(18) 1.3148(4) 0.25637(16) 0.0482(8) Uani 1 1 d .
C30 C 0.69476(17) 1.1632(3) 0.13586(15) 0.0410(7) Uani 1 1 d .
C31 C 0.61862(18) 1.1583(3) 0.16581(16) 0.0465(7) Uani 1 1 d .
C32 C 0.54556(19) 1.1508(4) 0.11855(18) 0.0553(8) Uani 1 1 d .
H32 H 0.4946 1.1470 0.1400 0.066 Uiso 1 1 calc R
C33 C 0.5493(2) 1.1493(3) 0.04166(18) 0.0556(9) Uani 1 1 d .
H33 H 0.5008 1.1442 0.0111 0.067 Uiso 1 1 calc R
C34 C 0.6321(3) 1.1549(4) -0.07225(18) 0.0624(10) Uani 1 1 d .
H34 H 0.5841 1.1493 -0.1036 0.075 Uiso 1 1 calc R
C35 C 0.7067(3) 1.1625(4) -0.10352(18) 0.0685(11) Uani 1 1 d .
H35 H 0.7096 1.1640 -0.1559 0.082 Uiso 1 1 calc R
C36 C 0.7786(2) 1.1678(4) -0.05661(18) 0.0660(10) Uani 1 1 d .
H36 H 0.8294 1.1727 -0.0782 0.079 Uiso 1 1 calc R
C37 C 0.7761(2) 1.1661(4) 0.02056(17) 0.0564(9) Uani 1 1 d .
H37 H 0.8251 1.1685 0.0506 0.068 Uiso 1 1 calc R
C38 C 0.69943(18) 1.1607(3) 0.05537(15) 0.0427(7) Uani 1 1 d .
C39 C 0.6263(2) 1.1552(3) 0.00796(16) 0.0473(7) Uani 1 1 d .
C100 C 1.0939(4) 0.2788(7) 0.4783(4) 0.126(2) Uani 1 1 d .
H100 H 1.1319 0.3216 0.4484 0.151 Uiso 1 1 calc R
C101 C 1.0698(3) 0.1400(6) 0.4651(3) 0.1068(17) Uani 1 1 d .
H101 H 1.0930 0.0906 0.4263 0.128 Uiso 1 1 calc R
C102 C 1.0129(2) 0.0736(4) 0.5073(2) 0.0663(10) Uani 1 1 d .
C103 C 0.9819(3) 0.1518(5) 0.5652(3) 0.0897(14) Uani 1 1 d .
H103 H 0.9439 0.1104 0.5957 0.108 Uiso 1 1 calc R
C104 C 1.0049(3) 0.2872(6) 0.5791(3) 0.1145(19) Uani 1 1 d .
H104 H 0.9824 0.3363 0.6184 0.137 Uiso 1 1 calc R
C105 C 1.0606(3) 0.3508(6) 0.5361(4) 0.1150(18) Uani 1 1 d .
H105 H 1.0760 0.4432 0.5459 0.138 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_3
C19 N11 C15 116.6(3) .
C14 N10 C10 116.4(3) .
N10 C10 C11 123.5(3) .
C12 C11 C10 120.7(3) .
C11 C12 C13 115.9(3) .
C11 C12 C17 121.8(3) .
C13 C12 C17 122.3(3) .
C14 C13 C12 120.2(3) .
N10 C14 C13 123.3(3) .
N11 C15 C16 123.5(4) .
C15 C16 C17 119.7(3) .
C18 C17 C16 116.7(3) .
C18 C17 C12 122.3(3) .
C16 C17 C12 121.0(3) .
C19 C18 C17 120.1(3) .
N11 C19 C18 123.4(3) .
C21 C20 C28 118.9(3) .
C21 C20 C30 121.0(3) .
C28 C20 C30 120.0(3) .
C20 C21 O21 119.4(3) .
C20 C21 C22 121.7(3) .
O21 C21 C22 118.9(3) .
C23 C22 C21 119.4(3) .
C22 C23 C29 121.6(3) .
C25 C24 C29 121.8(3) .
C24 C25 C26 119.5(4) .
C27 C26 C25 121.0(4) .
C26 C27 C28 121.2(3) .
C27 C28 C20 122.4(3) .
C27 C28 C29 117.9(3) .
C20 C28 C29 119.7(3) .
C23 C29 C24 122.8(3) .
C23 C29 C28 118.6(3) .
C24 C29 C28 118.6(3) .
C31 C30 C38 119.0(3) .
C31 C30 C20 120.1(2) .
C38 C30 C20 120.9(2) .
O31 C31 C30 118.7(3) .
O31 C31 C32 120.2(3) .
C30 C31 C32 121.1(3) .
C33 C32 C31 120.4(3) .
C32 C33 C39 120.7(3) .
C35 C34 C39 121.0(3) .
C34 C35 C36 119.6(3) .
C37 C36 C35 121.4(3) .
C36 C37 C38 120.7(3) .
C39 C38 C37 118.0(3) .
C39 C38 C30 120.0(3) .
C37 C38 C30 121.9(3) .
C38 C39 C33 118.8(3) .
C38 C39 C34 119.3(3) .
C33 C39 C34 121.9(3) .
C105 C100 C101 118.8(5) .
C102 C101 C100 122.4(5) .
C101 C102 C103 115.9(4) .
C101 C102 C102 122.1(5) 3_756
C103 C102 C102 121.9(5) 3_756
C104 C103 C102 122.4(5) .
C105 C104 C103 120.5(5) .
C104 C105 C100 119.9(6) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O21 C21 1.376(4) .
O31 C31 1.357(3) .
N11 C19 1.334(5) .
N11 C15 1.336(5) .
N10 C14 1.326(4) .
N10 C10 1.328(5) .
C10 C11 1.374(5) .
C11 C12 1.366(4) .
C12 C13 1.383(4) .
C12 C17 1.487(4) .
C13 C14 1.382(5) .
C15 C16 1.379(5) .
C16 C17 1.387(4) .
C17 C18 1.381(4) .
C18 C19 1.376(4) .
C20 C21 1.374(4) .
C20 C28 1.424(4) .
C20 C30 1.497(4) .
C21 C22 1.411(4) .
C22 C23 1.364(5) .
C23 C29 1.407(5) .
C24 C25 1.361(5) .
C24 C29 1.411(5) .
C25 C26 1.392(5) .
C26 C27 1.365(5) .
C27 C28 1.415(4) .
C28 C29 1.426(4) .
C30 C31 1.372(4) .
C30 C38 1.429(4) .
C31 C32 1.411(4) .
C32 C33 1.364(4) .
C33 C39 1.416(4) .
C34 C35 1.361(5) .
C34 C39 1.426(4) .
C35 C36 1.392(5) .
C36 C37 1.367(4) .
C37 C38 1.419(4) .
C38 C39 1.413(4) .
C100 C105 1.368(7) .
C100 C101 1.396(7) .
C101 C102 1.375(6) .
C102 C103 1.383(5) .
C102 C102 1.483(8) 3_756
C103 C104 1.363(7) .
C104 C105 1.356(7) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145693
