#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:17:34 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179622 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/86/4508697.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4508697
loop_
_publ_author_name
'Fridman, N.'
'Speiser, S.'
'Kaftory, M.'
_publ_section_title
;
 Structures and Chromogenic Properties of Bisimidazole Derivatives
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1653
_journal_paper_doi               10.1021/cg060107j
_journal_volume                  6
_journal_year                    2006
_chemical_formula_moiety         'C38 H30 N4, 2(C O H4)'
_chemical_formula_sum            'C40 H38 N4 O2'
_chemical_formula_weight         606.74
_chemical_name_systematic
;
 1H-Imidazole, 2,2'-(1,4-phenylene)bis[1-methyl-4,5-diphenyl]
 Methanol chlathrate
;
_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                 117.98(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.762(3)
_cell_length_b                   12.001(2)
_cell_length_c                   12.175(2)
_cell_measurement_reflns_used    2631
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      1.018
_cell_volume                     1646.7(6)
_computing_cell_refinement       'Denzo SMN (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius, 2000)'
_computing_data_reduction        'Denzo SMN (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 95
_diffrn_measured_fraction_theta_full 0.948
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi scan & omega 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  0.1121
_diffrn_reflns_av_sigmaI/netI    0.2468
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4740
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.48
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.729
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.729
_refine_ls_R_factor_all          0.2159
_refine_ls_R_factor_gt           0.0507
_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)+(0.0310P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.1142
_reflns_number_gt                881
_reflns_number_total             2773
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060107jsup10.cif
_cod_data_source_block           natalia86
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1646.7(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4508697
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
O1 O 0.3267(2) 0.5657(3) 0.2404(3) 0.1146(12) Uani 1 1 d .
H1 H 0.2983 0.5316 0.1744 0.138 Uiso 1 1 calc R
N1 N 0.2938(3) 0.1353(3) 0.6000(2) 0.0574(9) Uani 1 1 d .
N2 N 0.3733(2) 0.2771(3) 0.5477(2) 0.0522(8) Uani 1 1 d .
C1 C 0.2795(4) 0.4441(4) 0.5865(3) 0.0536(10) Uani 1 1 d .
C2 C 0.3750(4) 0.5145(4) 0.6458(4) 0.0678(12) Uani 1 1 d .
H2 H 0.4513 0.4855 0.6887 0.087(15) Uiso 1 1 calc R
C3 C 0.3569(5) 0.6302(4) 0.6413(4) 0.0737(13) Uani 1 1 d .
H3 H 0.4214 0.6780 0.6802 0.088(16) Uiso 1 1 calc R
C4 C 0.2457(5) 0.6723(5) 0.5803(4) 0.0778(14) Uani 1 1 d .
H4 H 0.2342 0.7490 0.5778 0.085(15) Uiso 1 1 calc R
C5 C 0.1487(5) 0.6023(4) 0.5217(4) 0.0727(13) Uani 1 1 d .
H5 H 0.0724 0.6315 0.4804 0.088(15) Uiso 1 1 calc R
C6 C 0.1665(4) 0.4887(4) 0.5251(4) 0.0657(12) Uani 1 1 d .
H6 H 0.1016 0.4414 0.4856 0.087(15) Uiso 1 1 calc R
C7 C 0.2970(3) 0.3228(4) 0.5870(3) 0.0537(11) Uani 1 1 d .
C8 C 0.2495(3) 0.2340(4) 0.6185(3) 0.0532(11) Uani 1 1 d .
C9 C 0.1598(3) 0.2299(4) 0.6633(3) 0.0589(11) Uani 1 1 d .
C10 C 0.1592(4) 0.3083(4) 0.7485(4) 0.0693(13) Uani 1 1 d .
H10 H 0.2140 0.3663 0.7753 0.102(19) Uiso 1 1 calc R
C11 C 0.0787(5) 0.3002(5) 0.7921(4) 0.0894(17) Uani 1 1 d .
H11 H 0.0793 0.3523 0.8490 0.084(14) Uiso 1 1 calc R
C12 C -0.0043(5) 0.2145(5) 0.7523(5) 0.101(2) Uani 1 1 d .
H12 H -0.0592 0.2089 0.7820 0.086(12) Uiso 1 1 calc R
C13 C -0.0040(5) 0.1398(5) 0.6702(5) 0.0990(17) Uani 1 1 d .
H13 H -0.0590 0.0821 0.6434 0.095(17) Uiso 1 1 calc R
C14 C 0.0762(4) 0.1475(4) 0.6254(4) 0.0757(13) Uani 1 1 d .
H14 H 0.0737 0.0952 0.5678 0.070(13) Uiso 1 1 calc R
C15 C 0.3689(3) 0.1637(4) 0.5571(3) 0.0511(10) Uani 1 1 d .
C16 C 0.4375(3) 0.0828(3) 0.5273(3) 0.0496(10) Uani 1 1 d .
C17 C 0.3901(4) -0.0232(4) 0.4875(3) 0.0625(12) Uani 1 1 d .
H17 H 0.3155 -0.0401 0.4790 0.073(12) Uiso 1 1 calc R
C18 C 0.4520(4) -0.1035(4) 0.4605(3) 0.0628(11) Uani 1 1 d .
H18 H 0.4180 -0.1733 0.4334 0.058(12) Uiso 1 1 calc R
C19 C 0.4264(4) 0.3393(4) 0.4792(4) 0.0772(13) Uani 1 1 d .
H19A H 0.3780 0.4028 0.4386 0.15(2) Uiso 1 1 calc R
H19B H 0.4303 0.2912 0.4183 0.111(16) Uiso 1 1 calc R
H19C H 0.5049 0.3636 0.5369 0.086(15) Uiso 1 1 calc R
C20 C 0.2381(4) 0.5948(4) 0.2681(4) 0.0934(15) Uani 1 1 d .
H20A H 0.2574 0.6645 0.3119 0.140 Uiso 1 1 calc R
H20B H 0.2298 0.5382 0.3192 0.140 Uiso 1 1 calc R
H20C H 0.1648 0.6022 0.1924 0.140 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'
O O 0.0106 0.0060 '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'
H H 0.0000 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
_geom_angle_site_symmetry_1
C20 O1 H1 109.5 .
C15 N1 C8 105.7(3) .
C15 N2 C7 107.5(3) .
C15 N2 C19 126.1(3) .
C7 N2 C19 124.8(4) .
C2 C1 C6 119.2(4) .
C2 C1 C7 120.7(4) .
C6 C1 C7 120.2(4) .
C1 C2 C3 119.9(5) .
C1 C2 H2 120.1 .
C3 C2 H2 120.1 .
C4 C3 C2 120.1(5) .
C4 C3 H3 120.0 .
C2 C3 H3 120.0 .
C3 C4 C5 120.7(5) .
C3 C4 H4 119.7 .
C5 C4 H4 119.7 .
C6 C5 C4 119.3(5) .
C6 C5 H5 120.4 .
C4 C5 H5 120.4 .
C5 C6 C1 120.9(5) .
C5 C6 H6 119.5 .
C1 C6 H6 119.5 .
C8 C7 N2 105.4(3) .
C8 C7 C1 133.3(3) .
N2 C7 C1 121.3(4) .
C7 C8 N1 110.8(3) .
C7 C8 C9 130.6(4) .
N1 C8 C9 118.6(4) .
C14 C9 C10 117.5(4) .
C14 C9 C8 121.0(4) .
C10 C9 C8 121.5(4) .
C11 C10 C9 120.4(5) .
C11 C10 H10 119.8 .
C9 C10 H10 119.8 .
C10 C11 C12 120.5(5) .
C10 C11 H11 119.8 .
C12 C11 H11 119.8 .
C13 C12 C11 119.0(5) .
C13 C12 H12 120.5 .
C11 C12 H12 120.5 .
C12 C13 C14 121.0(6) .
C12 C13 H13 119.5 .
C14 C13 H13 119.5 .
C9 C14 C13 121.6(5) .
C9 C14 H14 119.2 .
C13 C14 H14 119.2 .
N1 C15 N2 110.7(3) .
N1 C15 C16 123.5(4) .
N2 C15 C16 125.8(4) .
C18 C16 C17 117.4(4) 3_656
C18 C16 C15 124.0(4) 3_656
C17 C16 C15 118.6(4) .
C18 C17 C16 121.1(4) .
C18 C17 H17 119.5 .
C16 C17 H17 119.5 .
C16 C18 C17 121.5(4) 3_656
C16 C18 H18 119.2 3_656
C17 C18 H18 119.2 .
N2 C19 H19A 109.5 .
N2 C19 H19B 109.5 .
H19A C19 H19B 109.5 .
N2 C19 H19C 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
O1 C20 H20A 109.5 .
O1 C20 H20B 109.5 .
H20A C20 H20B 109.5 .
O1 C20 H20C 109.5 .
H20A C20 H20C 109.5 .
H20B C20 H20C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C20 1.368(3) .
O1 H1 0.8200 .
N1 C15 1.332(4) .
N1 C8 1.376(4) .
N2 C15 1.370(4) .
N2 C7 1.384(4) .
N2 C19 1.496(4) .
C1 C2 1.376(5) .
C1 C6 1.384(5) .
C1 C7 1.472(5) .
C2 C3 1.405(5) .
C2 H2 0.9300 .
C3 C4 1.353(5) .
C3 H3 0.9300 .
C4 C5 1.385(5) .
C4 H4 0.9300 .
C5 C6 1.379(5) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 C8 1.367(5) .
C8 C9 1.482(5) .
C9 C14 1.366(5) .
C9 C10 1.403(5) .
C10 C11 1.364(5) .
C10 H10 0.9300 .
C11 C12 1.390(6) .
C11 H11 0.9300 .
C12 C13 1.343(6) .
C12 H12 0.9300 .
C13 C14 1.370(5) .
C13 H13 0.9300 .
C14 H14 0.9300 .
C15 C16 1.462(4) .
C16 C18 1.369(4) 3_656
C16 C17 1.394(5) .
C17 C18 1.381(4) .
C17 H17 0.9300 .
C18 C16 1.369(4) 3_656
C18 H18 0.9300 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
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
C6 C1 C2 C3 -1.2(5) . .
C7 C1 C2 C3 178.2(3) . .
C1 C2 C3 C4 1.0(6) . .
C2 C3 C4 C5 -0.1(6) . .
C3 C4 C5 C6 -0.5(6) . .
C4 C5 C6 C1 0.2(5) . .
C2 C1 C6 C5 0.7(5) . .
C7 C1 C6 C5 -178.8(3) . .
C15 N2 C7 C8 0.0(4) . .
C19 N2 C7 C8 166.5(3) . .
C15 N2 C7 C1 -179.0(3) . .
C19 N2 C7 C1 -12.5(6) . .
C2 C1 C7 C8 127.6(4) . .
C6 C1 C7 C8 -53.0(6) . .
C2 C1 C7 N2 -53.8(5) . .
C6 C1 C7 N2 125.6(4) . .
N2 C7 C8 N1 0.0(4) . .
C1 C7 C8 N1 178.8(4) . .
N2 C7 C8 C9 -178.1(4) . .
C1 C7 C8 C9 0.7(7) . .
C15 N1 C8 C7 0.0(4) . .
C15 N1 C8 C9 178.4(3) . .
C7 C8 C9 C14 142.0(4) . .
N1 C8 C9 C14 -35.9(5) . .
C7 C8 C9 C10 -39.6(6) . .
N1 C8 C9 C10 142.4(3) . .
C14 C9 C10 C11 1.0(6) . .
C8 C9 C10 C11 -177.4(3) . .
C9 C10 C11 C12 -0.4(6) . .
C10 C11 C12 C13 0.0(7) . .
C11 C12 C13 C14 -0.2(8) . .
C10 C9 C14 C13 -1.3(6) . .
C8 C9 C14 C13 177.2(4) . .
C12 C13 C14 C9 0.9(7) . .
C8 N1 C15 N2 -0.1(4) . .
C8 N1 C15 C16 178.9(3) . .
C7 N2 C15 N1 0.1(4) . .
C19 N2 C15 N1 -166.2(3) . .
C7 N2 C15 C16 -178.8(3) . .
C19 N2 C15 C16 14.9(6) . .
N1 C15 C16 C18 -148.3(4) . 3_656
N2 C15 C16 C18 30.5(6) . 3_656
N1 C15 C16 C17 29.7(5) . .
N2 C15 C16 C17 -151.6(4) . .
C18 C16 C17 C18 -0.6(6) 3_656 .
C15 C16 C17 C18 -178.7(3) . .
C16 C17 C18 C16 0.6(6) . 3_656
