#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/73/2007325.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_2007325
loop_
_publ_author_name
'García-Martínez, Emilia'
'Vázquez-López, Ezequiel M.'
'Tuck, Dennis G.'
_publ_section_title
;
 Hydrogen Bonding in the 1:1 Adduct of 1,10-Phenanthroline and
 1,1'-Binaphthyl-2,2'-diol
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              840
_journal_page_last               842
_journal_paper_doi               10.1107/S0108270197019987
_journal_volume                  54
_journal_year                    1998
_chemical_formula_sum            'C32 H22 N2 O2'
_chemical_formula_weight         466.52
_chemical_name_systematic
;
 adduct of 1,10-Phenanthroline and 1,1'-Binaphthyl-2,2'-diol
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.929(8)
_cell_angle_beta                 110.895(7)
_cell_angle_gamma                109.635(9)
_cell_formula_units_Z            2
_cell_length_a                   10.8768(15)
_cell_length_b                   11.238(2)
_cell_length_c                   11.6786(8)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42
_cell_measurement_theta_min      9
_cell_volume                     1201.0(3)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1995)'
_computing_data_reduction        'HELENA (Spek, 1996)'
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  SHELXL97
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_av_sigmaI/netI    0.045
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5148
_diffrn_reflns_theta_full        74.30
_diffrn_reflns_theta_max         74.30
_diffrn_reflns_theta_min         4.24
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.139
_refine_ls_extinction_coef       0.0064(5)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment
'H atoms treated by a mixture of independent and constrained refinement'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         4896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.100
_refine_ls_R_factor_gt           0.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0559P)²+0.1363P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.129
_reflns_number_gt                2916
_reflns_number_total             4896
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg1399.cif
_cod_data_source_block           PHENBINAP
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0559P)^2^+0.1363P] where P = (Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0559P)^2^+0.1363P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_formula_sum        'C12 H8 N2, C20 H14 O2'
_cod_database_code               2007325
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
N1 .4352(2) .65086(18) .53783(17) .0615(5) Uani d . 1 . . N
N2 .62702(18) .90958(16) .64234(15) .0531(4) Uani d . 1 . . N
C2 .3404(3) .5263(2) .4856(3) .0757(7) Uani d . 1 . . C
H2 .3161 .4789 .5394 .110(11) Uiso calc R 1 . . H
C3 .2745(3) .4616(3) .3546(3) .0802(8) Uani d . 1 . . C
H3 .2081 .3736 .3226 .099(9) Uiso calc R 1 . . H
C4 .3090(3) .5292(2) .2746(2) .0708(7) Uani d . 1 . . C
H4 .2654 .4879 .1868 .086(8) Uiso calc R 1 . . H
C5 .4106(2) .6620(2) .32462(19) .0551(5) Uani d . 1 . . C
C6 .4704(2) .7181(2) .45810(18) .0495(5) Uani d . 1 . . C
C7 .4543(3) .7396(2) .2473(2) .0662(6) Uani d . 1 . . C
H7 .4140 .7020 .1591 .077(7) Uiso calc R 1 . . H
C8 .5526(3) .8662(2) .3001(2) .0634(6) Uani d . 1 . . C
H8 .5810 .9141 .2482 .079(8) Uiso calc R 1 . . H
C9 .6138(2) .9277(2) .43465(19) .0505(5) Uani d . 1 . . C
C10 .5739(2) .85480(19) .51415(18) .0464(4) Uani d . 1 . . C
C11 .7194(2) 1.0357(2) .6914(2) .0608(6) Uani d . 1 . . C
H11 .7559 1.0736 .7792 .067(7) Uiso calc R 1 . . H
C12 .7651(2) 1.1149(2) .6206(2) .0643(6) Uani d . 1 . . C
H12 .8310 1.2028 .6600 .090(8) Uiso calc R 1 . . H
C13 .7111(2) 1.0607(2) .4920(2) .0615(6) Uani d . 1 . . C
H13 .7389 1.1121 .4422 .077(7) Uiso calc R 1 . . H
O1 .38076(18) .91075(16) 1.03452(13) .0667(5) Uani d . 1 . . O
H1A .426(3) .998(3) 1.093(3) .115(10) Uiso d . 1 . . H
O2 .47763(16) .84426(14) .78448(13) .0538(4) Uani d . 1 . . O
H2A .524(3) .835(3) .732(3) .114(10) Uiso d . 1 . . H
C14 .2747(2) .90142(19) .92226(17) .0498(5) Uani d . 1 . . C
C15 .2154(3) .9956(2) .9153(2) .0641(6) Uani d . 1 . . C
H15 .2491 1.0654 .9875 .070(7) Uiso calc R 1 . . H
C16 .1090(2) .9842(2) .8032(2) .0639(6) Uani d . 1 . . C
H16 .0706 1.0468 .7997 .079(7) Uiso calc R 1 . . H
C17 .0557(2) .87979(18) .69217(18) .0487(5) Uani d . 1 . . C
C18 .1155(2) .78497(17) .69912(17) .0421(4) Uani d . 1 . . C
C19 .22695(19) .79727(17) .81734(16) .0416(4) Uani d . 1 . . C
C20 .0651(2) .68371(18) .58525(17) .0469(5) Uani d . 1 . . C
H20 .1029 .6206 .5873 .052(6) Uiso calc R 1 . . H
C21 -.0379(2) .6774(2) .47269(19) .0563(5) Uani d . 1 . . C
H21 -.0688 .6107 .3988 .055(6) Uiso calc R 1 . . H
C22 -.0978(2) .7698(2) .4668(2) .0624(6) Uani d . 1 . . C
H22 -.1689 .7637 .3897 .084(8) Uiso calc R 1 . . H
C23 -.0523(2) .8687(2) .5739(2) .0608(6) Uani d . 1 . . C
H23 -.0927 .9298 .5694 .070(7) Uiso calc R 1 . . H
C24 .4179(2) .72768(18) .80879(16) .0451(4) Uani d . 1 . . C
C25 .2943(2) .70099(17) .82697(15) .0411(4) Uani d . 1 . . C
C26 .2324(2) .58045(17) .85336(15) .0433(4) Uani d . 1 . . C
C27 .3004(2) .49180(18) .86214(16) .0480(5) Uani d . 1 . . C
C28 .4274(2) .5251(2) .84359(19) .0572(5) Uani d . 1 . . C
H28 .4726 .4677 .8494 .069(7) Uiso calc R 1 . . H
C29 .4849(2) .6396(2) .81734(19) .0552(5) Uani d . 1 . . C
H29 .5686 .6598 .8050 .072(7) Uiso calc R 1 . . H
C30 .2372(3) .3718(2) .88762(19) .0605(6) Uani d . 1 . . C
H30 .2822 .3142 .8952 .066(7) Uiso calc R 1 . . H
C31 .1124(3) .3396(2) .9012(2) .0663(6) Uani d . 1 . . C
H31 .0724 .2606 .9179 .073(7) Uiso calc R 1 . . H
C32 .0440(3) .4258(2) .8899(2) .0632(6) Uani d . 1 . . C
H32 -.0426 .4026 .8975 .080(8) Uiso calc R 1 . . H
C33 .1027(2) .54322(19) .86791(19) .0534(5) Uani d . 1 . . C
H33 .0564 .5998 .8624 .057(6) Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_publ_flag
C2 N1 C6 117.2(2) y
C11 N2 C10 117.57(19) y
N1 C2 C3 124.0(3) y
C4 C3 C2 118.9(2) ?
C3 C4 C5 119.9(2) ?
C4 C5 C6 116.7(2) ?
C4 C5 C7 123.4(2) ?
C6 C5 C7 119.9(2) ?
N1 C6 C5 123.4(2) y
N1 C6 C10 117.73(18) y
C5 C6 C10 118.86(19) ?
C8 C7 C5 121.1(2) ?
C7 C8 C9 120.8(2) ?
C13 C9 C10 117.69(19) ?
C13 C9 C8 122.4(2) ?
C10 C9 C8 119.8(2) ?
N2 C10 C9 122.05(19) y
N2 C10 C6 118.49(18) y
C9 C10 C6 119.44(18) ?
N2 C11 C12 124.3(2) y
C13 C12 C11 118.3(2) ?
C12 C13 C9 120.1(2) ?
H1A O1 C14 110.9(17) no
H2A O2 C24 111.0(18) no
O1 C14 C19 118.01(16) y
O1 C14 C15 120.69(17) y
C19 C14 C15 121.30(17) ?
C16 C15 C14 119.96(19) ?
C15 C16 C17 121.43(18) ?
C16 C17 C23 122.03(18) ?
C16 C17 C18 118.61(17) ?
C23 C17 C18 119.34(18) ?
C20 C18 C17 117.92(16) ?
C20 C18 C19 122.36(16) ?
C17 C18 C19 119.67(16) ?
C14 C19 C18 119.04(16) ?
C14 C19 C25 120.00(16) ?
C18 C19 C25 120.94(15) ?
C21 C20 C18 120.95(18) ?
C20 C21 C22 120.86(19) ?
C23 C22 C21 120.02(19) ?
C22 C23 C17 120.89(19) ?
O2 C24 C25 118.64(16) y
O2 C24 C29 119.91(19) y
C25 C24 C29 121.43(19) ?
C24 C25 C26 118.87(16) ?
C24 C25 C19 119.68(17) ?
C26 C25 C19 121.44(17) ?
C33 C26 C27 118.02(18) ?
C33 C26 C25 122.38(16) ?
C27 C26 C25 119.58(18) ?
C28 C27 C30 122.10(19) ?
C28 C27 C26 118.89(18) ?
C30 C27 C26 119.0(2) ?
C29 C28 C27 121.17(18) ?
C28 C29 C24 120.0(2) ?
C31 C30 C27 121.2(2) ?
C30 C31 C32 119.8(2) ?
C33 C32 C31 120.9(2) ?
C32 C33 C26 121.2(2) ?
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
N1 C2 . 1.319(3) y
N1 C6 . 1.356(3) y
N2 C11 . 1.324(3) y
N2 C10 . 1.358(2) y
C2 C3 . 1.394(3) y
C3 C4 . 1.359(4) ?
C4 C5 . 1.407(3) ?
C5 C6 . 1.407(3) y
C5 C7 . 1.430(3) ?
C6 C10 . 1.446(3) y
C7 C8 . 1.347(3) ?
C8 C9 . 1.427(3) ?
C9 C13 . 1.399(3) ?
C9 C10 . 1.407(3) y
C11 C12 . 1.387(3) y
C12 C13 . 1.359(3) ?
O1 H1A . .96(3) no
O2 H2A . .94(3) no
O1 C14 . 1.365(2) y
O2 C24 . 1.372(2) y
C14 C19 . 1.372(2) y
C14 C15 . 1.409(3) y
C15 C16 . 1.358(3) ?
C16 C17 . 1.408(3) ?
C17 C23 . 1.414(3) ?
C17 C18 . 1.420(2) ?
C18 C20 . 1.417(2) ?
C18 C19 . 1.427(2) y
C19 C25 . 1.492(2) y
C20 C21 . 1.364(2) ?
C21 C22 . 1.397(3) ?
C22 C23 . 1.360(3) ?
C24 C25 . 1.376(3) y
C24 C29 . 1.407(3) y
C25 C26 . 1.426(3) y
C26 C33 . 1.410(3) ?
C26 C27 . 1.421(2) ?
C27 C28 . 1.408(3) ?
C27 C30 . 1.419(3) ?
C28 C29 . 1.359(3) ?
C30 C31 . 1.356(3) ?
C31 C32 . 1.399(3) ?
C32 C33 . 1.364(3) ?
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
O1 H1A O2 2_677 0.96(3) 1.81(3) 2.765(2) 174(2)
O2 H2A N1 . 0.94(3) 2.48(3) 3.144(2) 128(2)
O2 H2A N2 . 0.94(3) 1.87(3) 2.719(2) 149(2)
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_publ_flag
H1A O1 C14 C15 -17.6(19) y
H2A O2 C24 C25 -149.1(18) y
C18 C19 C25 C26 -86.5(2) y
C18 C19 C25 C24 92.8(2) y
C14 C19 C25 C26 95.1(2) y
C14 C19 C25 C24 -85.5(2) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21137058
