#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:32:33 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179584 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/49/4504998.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_4504998
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            'C37 H30 N2 O2'
_chemical_formula_weight         534.63
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 93.59(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.950(6)
_cell_length_b                   9.809(2)
_cell_length_c                   19.848(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      8
_cell_volume                     5819(2)
_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 0.840
_diffrn_measured_fraction_theta_max 0.840
_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  0.0178
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4399
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            dirty-white
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needles
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         4297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1411
_refine_ls_R_factor_gt           0.0636
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0892P)²+4.2263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1617
_refine_ls_wR_factor_ref         0.2257
_reflns_number_gt                2080
_reflns_number_total             4297
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg049761usi20040712_065649.cif
_cod_data_source_block           1
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        5820(2)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4504998
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'
'-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_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 0.41467(13) -0.1137(3) 0.32395(13) 0.1149(11) Uani 1 1 d .
H21O H 0.441(2) -0.189(8) 0.343(4) 0.23(3) Uiso 1 1 d .
O31 O 0.31033(15) 0.0443(3) 0.30938(14) 0.1229(12) Uani 1 1 d .
H31O H 0.276(3) 0.067(9) 0.297(5) 0.28(4) Uiso 1 1 d .
N11 N 0.21880(16) 0.0535(4) 0.2916(2) 0.1202(13) Uani 1 1 d .
N10 N -0.00485(16) 0.2461(4) 0.34539(18) 0.1129(13) Uani 1 1 d .
C10 C 0.0281(3) 0.3363(5) 0.3421(2) 0.1212(18) Uani 1 1 d .
H10 H 0.0211 0.4279 0.3472 0.145 Uiso 1 1 calc R
C11 C 0.0717(2) 0.3040(4) 0.3317(2) 0.1117(16) Uani 1 1 d .
H11 H 0.0929 0.3727 0.3292 0.134 Uiso 1 1 calc R
C12 C 0.08400(19) 0.1692(4) 0.32499(18) 0.0956(13) Uani 1 1 d .
C13 C 0.0502(2) 0.0749(4) 0.3288(2) 0.1129(16) Uani 1 1 d .
H13 H 0.0564 -0.0175 0.3245 0.135 Uiso 1 1 calc R
C14 C 0.0075(2) 0.1169(5) 0.3391(2) 0.1209(17) Uani 1 1 d .
H14 H -0.0143 0.0502 0.3419 0.145 Uiso 1 1 calc R
C15 C 0.2000(2) 0.1668(6) 0.2653(2) 0.1219(17) Uani 1 1 d .
H15 H 0.2172 0.2218 0.2389 0.146 Uiso 1 1 calc R
C16 C 0.1575(2) 0.2069(5) 0.2748(2) 0.1126(16) Uani 1 1 d .
H16 H 0.1466 0.2876 0.2554 0.135 Uiso 1 1 calc R
C17 C 0.12998(19) 0.1282(4) 0.31329(18) 0.0947(13) Uani 1 1 d .
C18 C 0.1487(2) 0.0101(4) 0.3402(2) 0.1076(15) Uani 1 1 d .
H18 H 0.1322 -0.0466 0.3667 0.129 Uiso 1 1 calc R
C19 C 0.1917(2) -0.0228(5) 0.3275(2) 0.1181(17) Uani 1 1 d .
H19 H 0.2031 -0.1044 0.3452 0.142 Uiso 1 1 calc R
C20 C 0.39990(15) 0.1237(4) 0.32985(15) 0.0898(12) Uani 1 1 d .
C21 C 0.41789(16) 0.0066(4) 0.35879(17) 0.0988(13) Uani 1 1 d .
C22 C 0.43905(17) 0.0111(5) 0.42396(18) 0.1157(16) Uani 1 1 d .
H22 H 0.4504 -0.0689 0.4435 0.139 Uiso 1 1 calc R
C23 C 0.44329(18) 0.1294(6) 0.45886(18) 0.1205(17) Uani 1 1 d .
H23 H 0.4575 0.1294 0.5019 0.145 Uiso 1 1 calc R
C24 C 0.4310(2) 0.3761(6) 0.4655(2) 0.1287(18) Uani 1 1 d .
H24 H 0.4458 0.3776 0.5081 0.154 Uiso 1 1 calc R
C25 C 0.4144(2) 0.4943(6) 0.4390(3) 0.139(2) Uani 1 1 d .
H25 H 0.4175 0.5752 0.4633 0.166 Uiso 1 1 calc R
C26 C 0.3925(2) 0.4930(5) 0.3744(2) 0.1291(18) Uani 1 1 d .
H26 H 0.3811 0.5736 0.3555 0.155 Uiso 1 1 calc R
C27 C 0.38765(17) 0.3738(4) 0.33917(19) 0.1077(15) Uani 1 1 d .
H27 H 0.3729 0.3749 0.2965 0.129 Uiso 1 1 calc R
C28 C 0.40445(16) 0.2485(4) 0.36555(16) 0.0937(13) Uani 1 1 d .
C29 C 0.42658(18) 0.2519(5) 0.43102(17) 0.1079(15) Uani 1 1 d .
C30 C 0.37615(18) 0.1190(4) 0.26096(16) 0.0900(13) Uani 1 1 d .
C31 C 0.3321(2) 0.0803(4) 0.25360(19) 0.1000(14) Uani 1 1 d .
C32 C 0.30892(18) 0.0755(4) 0.1886(2) 0.1074(15) Uani 1 1 d .
H32 H 0.2790 0.0501 0.1843 0.129 Uiso 1 1 calc R
C33 C 0.3311(2) 0.1085(4) 0.1332(2) 0.1095(16) Uani 1 1 d .
H33 H 0.3159 0.1048 0.0910 0.131 Uiso 1 1 calc R
C34 C 0.3997(2) 0.1805(4) 0.07967(19) 0.1140(18) Uani 1 1 d .
H34 H 0.3848 0.1766 0.0371 0.137 Uiso 1 1 calc R
C35 C 0.4428(2) 0.2167(5) 0.0851(2) 0.1163(17) Uani 1 1 d .
H35 H 0.4574 0.2392 0.0466 0.140 Uiso 1 1 calc R
C36 C 0.46623(18) 0.2211(4) 0.14842(18) 0.1042(14) Uani 1 1 d .
H36 H 0.4963 0.2449 0.1519 0.125 Uiso 1 1 calc R
C37 C 0.44447(19) 0.1900(4) 0.20544(17) 0.0962(14) Uani 1 1 d .
H37 H 0.4602 0.1942 0.2473 0.115 Uiso 1 1 calc R
C38 C 0.39931(18) 0.1522(3) 0.20212(16) 0.0881(13) Uani 1 1 d .
C39 C 0.3760(2) 0.1478(4) 0.13729(17) 0.0941(14) Uani 1 1 d .
C101 C 0.2234(13) -0.370(2) 0.5513(12) 0.196(11) Uani 0.50 1 d P
C102 C 0.2969(8) -0.3651(17) 0.4609(10) 0.166(6) Uani 0.50 1 d P
C103 C 0.2662(7) -0.241(2) 0.4777(7) 0.172(7) Uani 0.50 1 d P
C104 C 0.3028(4) -0.236(2) 0.4327(5) 0.212(4) Uani 1 1 d .
C105 C 0.2592(5) -0.3705(8) 0.5077(6) 0.167(4) Uani 1 1 d .
C201 C 0.2899(14) 0.258(2) 0.439(2) 0.212(16) Uani 0.50 1 d P
C202 C 0.2115(17) 0.287(2) 0.439(2) 0.198(13) Uani 0.50 1 d P
C203 C 0.2168(6) 0.2728(12) 0.4922(9) 0.119(4) Uani 0.50 1 d P
C204 C 0.1754(6) 0.2863(13) 0.4961(12) 0.265(6) Uani 1 1 d .
C205 C 0.2500(9) 0.2686(9) 0.4419(4) 0.165(4) Uani 1 1 d .
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
C15 N11 C19 114.7(5) . .
C14 N10 C10 114.7(5) . .
N10 C10 C11 124.7(5) . .
C10 C11 C12 120.0(5) . .
C13 C12 C11 115.8(5) . .
C13 C12 C17 121.6(4) . .
C11 C12 C17 122.5(4) . .
C12 C13 C14 120.1(5) . .
N10 C14 C13 124.7(5) . .
N11 C15 C16 124.2(5) . .
C15 C16 C17 120.5(5) . .
C18 C17 C16 116.0(5) . .
C18 C17 C12 122.1(4) . .
C16 C17 C12 121.9(4) . .
C19 C18 C17 119.5(5) . .
N11 C19 C18 125.1(5) . .
C21 C20 C28 119.2(3) . .
C21 C20 C30 120.3(3) . .
C28 C20 C30 120.4(3) . .
O21 C21 C20 119.6(3) . .
O21 C21 C22 120.4(4) . .
C20 C21 C22 120.0(4) . .
C23 C22 C21 121.4(4) . .
C22 C23 C29 120.9(4) . .
C25 C24 C29 122.2(4) . .
C24 C25 C26 119.1(4) . .
C27 C26 C25 120.3(5) . .
C26 C27 C28 122.0(4) . .
C20 C28 C27 123.0(3) . .
C20 C28 C29 120.1(4) . .
C27 C28 C29 116.9(3) . .
C24 C29 C23 122.2(4) . .
C24 C29 C28 119.4(4) . .
C23 C29 C28 118.4(4) . .
C31 C30 C38 119.2(4) . .
C31 C30 C20 120.2(4) . .
C38 C30 C20 120.6(4) . .
O31 C31 C30 119.4(4) . .
O31 C31 C32 119.5(5) . .
C30 C31 C32 121.1(4) . .
C33 C32 C31 119.1(5) . .
C32 C33 C39 122.5(4) . .
C35 C34 C39 121.5(5) . .
C34 C35 C36 120.5(5) . .
C37 C36 C35 119.7(5) . .
C36 C37 C38 121.8(4) . .
C37 C38 C39 117.9(4) . .
C37 C38 C30 122.5(4) . .
C39 C38 C30 119.6(5) . .
C33 C39 C34 122.9(4) . .
C33 C39 C38 118.4(4) . .
C34 C39 C38 118.7(5) . .
C103 C101 C104 67.5(18) 7_546 7_546
C103 C101 C105 61(2) 7_546 .
C104 C101 C105 128(2) 7_546 .
C104 C102 C105 113.4(15) . .
C104 C102 C103 58.4(10) . .
C105 C102 C103 55.0(11) . .
C101 C103 C103 127(4) 7_546 7_546
C101 C103 C105 65(2) 7_546 7_546
C103 C103 C105 63(2) 7_546 7_546
C101 C103 C105 173(3) 7_546 .
C103 C103 C105 59.1(16) 7_546 .
C105 C103 C105 121.7(17) 7_546 .
C101 C103 C104 59(2) 7_546 .
C103 C103 C104 174(3) 7_546 .
C105 C103 C104 123.2(19) 7_546 .
C105 C103 C104 115(2) . .
C101 C103 C102 113(3) 7_546 .
C103 C103 C102 119(3) 7_546 .
C105 C103 C102 177.7(19) 7_546 .
C105 C103 C102 60.1(13) . .
C104 C103 C102 54.9(15) . .
C101 C104 C102 121(2) 7_546 .
C101 C104 C103 53.9(15) 7_546 .
C102 C104 C103 66.7(17) . .
C103 C105 C101 54.4(12) 7_546 .
C103 C105 C103 58.3(17) 7_546 .
C101 C105 C103 112.6(19) . .
C103 C105 C102 123.2(14) 7_546 .
C101 C105 C102 177.5(13) . .
C103 C105 C102 64.9(13) . .
C205 C201 C203 77.2(15) . 7_556
C205 C201 C204 125(2) . 7_556
C203 C201 C204 47.5(16) 7_556 7_556
C203 C202 C205 81(2) . .
C203 C202 C204 51(3) . .
C205 C202 C204 132(3) . .
C202 C203 C204 88(3) . .
C202 C203 C201 163(3) . 7_556
C204 C203 C201 76.2(18) . 7_556
C202 C203 C205 52(2) . .
C204 C203 C205 140(2) . .
C201 C203 C205 143(2) 7_556 .
C202 C203 C205 150(3) . 7_556
C204 C203 C205 121.9(17) . 7_556
C201 C203 C205 45.7(14) 7_556 7_556
C205 C203 C205 97.8(12) . 7_556
C202 C203 C203 105(3) . 7_556
C204 C203 C203 166(2) . 7_556
C201 C203 C203 90(2) 7_556 7_556
C205 C203 C203 52.9(11) . 7_556
C205 C203 C203 44.9(10) 7_556 7_556
C203 C204 C202 41.3(10) . .
C203 C204 C201 56.2(13) . 7_556
C202 C204 C201 97.3(16) . 7_556
C202 C205 C201 174(2) . .
C202 C205 C203 46.5(19) . .
C201 C205 C203 138.8(18) . .
C202 C205 C203 129(2) . 7_556
C201 C205 C203 57.1(18) . 7_556
C203 C205 C203 82.2(12) . 7_556
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O21 C21 1.368(4) .
O31 C31 1.367(5) .
N11 C15 1.337(6) .
N11 C19 1.341(6) .
N10 C14 1.328(6) .
N10 C10 1.331(6) .
C10 C11 1.370(7) .
C11 C12 1.381(6) .
C12 C13 1.376(6) .
C12 C17 1.467(6) .
C13 C14 1.372(7) .
C15 C16 1.359(7) .
C16 C17 1.391(6) .
C17 C18 1.379(6) .
C18 C19 1.368(7) .
C20 C21 1.378(5) .
C20 C28 1.417(5) .
C20 C30 1.502(5) .
C21 C22 1.405(5) .
C22 C23 1.353(6) .
C23 C29 1.402(6) .
C24 C25 1.355(7) .
C24 C29 1.400(6) .
C25 C26 1.403(7) .
C26 C27 1.366(5) .
C27 C28 1.416(5) .
C28 C29 1.422(5) .
C30 C31 1.371(6) .
C30 C38 1.433(5) .
C31 C32 1.427(5) .
C32 C33 1.360(6) .
C33 C39 1.395(6) .
C34 C35 1.339(7) .
C34 C39 1.419(6) .
C35 C36 1.401(6) .
C36 C37 1.375(6) .
C37 C38 1.400(6) .
C38 C39 1.426(5) .
C101 C103 1.28(3) 7_546
C101 C104 1.35(3) 7_546
C101 C105 1.42(4) .
C102 C104 1.40(2) .
C102 C105 1.51(2) .
C102 C103 1.57(4) .
C103 C101 1.28(3) 7_546
C103 C103 1.36(4) 7_546
C103 C105 1.37(2) 7_546
C103 C105 1.42(2) .
C103 C104 1.46(2) .
C104 C101 1.35(3) 7_546
C105 C103 1.37(2) 7_546
C201 C205 1.20(2) .
C201 C203 1.41(4) 7_556
C201 C204 1.65(5) 7_556
C202 C203 1.07(4) .
C202 C205 1.16(3) .
C202 C204 1.61(6) .
C203 C204 1.25(2) .
C203 C201 1.41(4) 7_556
C203 C205 1.45(3) .
C203 C205 1.64(2) 7_556
C203 C203 2.04(4) 7_556
C204 C201 1.65(5) 7_556
C205 C203 1.64(2) 7_556
