#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:41:09 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179671 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/24/4512420.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_4512420
loop_
_publ_author_name
'Dey, Avishek'
'Bera, Saibal'
'Biradha, Kumar'
_publ_section_title
;
 Cocrystals and Salts of Pyridine-3,5-bis(1-methyl-benzimidazole-2-yl)
 with Pyromellitic Acid: Aromatic Guest Inclusion and Separation via
 Benzimidazole--Carboxylic Acid Heterosynthon
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              318
_journal_paper_doi               10.1021/cg501380m
_journal_volume                  15
_journal_year                    2015
_chemical_formula_sum            'C82 H62 N10 O18'
_chemical_formula_weight         1475.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.520(11)
_cell_angle_beta                 97.062(12)
_cell_angle_gamma                109.545(11)
_cell_formula_units_Z            1
_cell_length_a                   10.635(4)
_cell_length_b                   11.379(4)
_cell_length_c                   14.710(5)
_cell_measurement_reflns_used    20882
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      1.42
_cell_volume                     1636.4(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_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  0.0807
_diffrn_reflns_av_sigmaI/netI    0.1269
_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       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20882
_diffrn_reflns_theta_full        26.32
_diffrn_reflns_theta_max         26.32
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_platon_squeeze_details
;
;
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.831
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         6485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.831
_refine_ls_R_factor_all          0.1557
_refine_ls_R_factor_gt           0.0697
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1689
_refine_ls_wR_factor_ref         0.1953
_reflns_number_gt                2681
_reflns_number_total             6485
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg501380m_si_002.cif
_cod_data_source_block           5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 4512417--4512422.cif.
;
_cod_original_cell_volume        1636.3(10)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4512420
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1W O 1.0509(3) 1.0496(3) -0.25276(19) 0.0593(8) Uani 1 1 d .
H1W H 1.097(3) 1.021(3) -0.300(2) 0.050 Uiso 1 1 d .
H2W H 0.987(4) 1.049(4) -0.283(3) 0.050 Uiso 1 1 d .
N21 N 0.6364(3) 0.6517(3) -0.3725(2) 0.0491(8) Uani 1 1 d .
N22 N 0.7110(3) 0.6806(3) -0.5058(2) 0.0496(8) Uani 1 1 d .
N11 N 1.2500(3) 0.9190(3) -0.1403(2) 0.0496(9) Uani 1 1 d .
H11N H 1.306(3) 0.936(3) -0.187(2) 0.050 Uiso 1 1 d .
N12 N 1.0741(3) 0.8366(3) -0.0749(2) 0.0477(8) Uani 1 1 d .
N1 N 1.0700(4) 0.6077(4) -0.3746(3) 0.0790(12) Uani 1 1 d .
C1 C 1.1230(4) 0.6809(5) -0.2904(3) 0.0697(13) Uani 1 1 d .
H1 H 1.2085 0.6863 -0.2622 0.084 Uiso 1 1 calc R
C2 C 1.0569(4) 0.7497(4) -0.2426(2) 0.0492(10) Uani 1 1 d .
C3 C 0.9295(4) 0.7430(4) -0.2839(3) 0.0494(10) Uani 1 1 d .
H3 H 0.8823 0.7866 -0.2532 0.059 Uiso 1 1 calc R
C4 C 0.8741(4) 0.6700(4) -0.3720(2) 0.0470(10) Uani 1 1 d .
C5 C 0.9482(4) 0.6061(4) -0.4138(3) 0.0701(13) Uani 1 1 d .
H5 H 0.9111 0.5585 -0.4733 0.084 Uiso 1 1 calc R
C11 C 1.1269(4) 0.8338(4) -0.1533(2) 0.0494(10) Uani 1 1 d .
C12 C 1.2829(4) 0.9834(4) -0.0480(2) 0.0451(10) Uani 1 1 d .
C13 C 1.1736(4) 0.9310(4) -0.0063(2) 0.0462(10) Uani 1 1 d .
C14 C 1.1759(5) 0.9718(4) 0.0882(3) 0.0637(12) Uani 1 1 d .
H14 H 1.1023 0.9362 0.1166 0.076 Uiso 1 1 calc R
C15 C 1.2897(5) 1.0649(4) 0.1362(3) 0.0645(12) Uani 1 1 d .
H15 H 1.2944 1.0940 0.1990 0.077 Uiso 1 1 calc R
C16 C 1.4002(5) 1.1186(4) 0.0940(3) 0.0646(12) Uani 1 1 d .
H16 H 1.4763 1.1833 0.1294 0.077 Uiso 1 1 calc R
C17 C 1.4002(4) 1.0794(4) 0.0025(3) 0.0565(11) Uani 1 1 d .
H17 H 1.4748 1.1149 -0.0251 0.068 Uiso 1 1 calc R
C18 C 0.9447(4) 0.7550(4) -0.0586(3) 0.0651(12) Uani 1 1 d .
H18A H 0.9423 0.7682 0.0068 0.098 Uiso 1 1 calc R
H18B H 0.9330 0.6680 -0.0801 0.098 Uiso 1 1 calc R
H18C H 0.8731 0.7747 -0.0919 0.098 Uiso 1 1 calc R
C21 C 0.7417(4) 0.6660(4) -0.4157(2) 0.0495(10) Uani 1 1 d .
C22 C 0.5323(4) 0.6578(3) -0.4373(2) 0.0436(9) Uani 1 1 d .
C23 C 0.5791(4) 0.6743(3) -0.5205(2) 0.0486(10) Uani 1 1 d .
C24 C 0.4973(5) 0.6863(4) -0.5983(3) 0.0631(12) Uani 1 1 d .
H24 H 0.5282 0.6976 -0.6541 0.076 Uiso 1 1 calc R
C25 C 0.3692(5) 0.6804(4) -0.5878(3) 0.0647(12) Uani 1 1 d .
H25 H 0.3113 0.6862 -0.6384 0.078 Uiso 1 1 calc R
C26 C 0.3232(4) 0.6660(4) -0.5043(3) 0.0559(11) Uani 1 1 d .
H26 H 0.2367 0.6659 -0.4997 0.067 Uiso 1 1 calc R
C27 C 0.4020(4) 0.6519(4) -0.4282(3) 0.0531(11) Uani 1 1 d .
H27 H 0.3695 0.6389 -0.3731 0.064 Uiso 1 1 calc R
C28 C 0.8007(4) 0.7066(5) -0.5752(3) 0.0729(14) Uani 1 1 d .
H28A H 0.7501 0.7110 -0.6326 0.109 Uiso 1 1 calc R
H28B H 0.8363 0.6398 -0.5858 0.109 Uiso 1 1 calc R
H28C H 0.8741 0.7859 -0.5525 0.109 Uiso 1 1 calc R
O1A O 0.7937(3) 1.0362(3) -0.62865(18) 0.0728(9) Uani 1 1 d .
O2A O 0.6164(3) 1.0397(3) -0.71932(18) 0.0598(8) Uani 1 1 d .
O3A O 0.8710(3) 1.0313(4) -0.4689(2) 0.0934(13) Uani 1 1 d .
H3OA H 0.835(6) 1.010(6) -0.529(4) 0.140 Uiso 1 1 d .
O4A O 0.7880(3) 0.9917(3) -0.3461(2) 0.0761(10) Uani 1 1 d .
C1A C 0.5396(3) 0.9882(3) -0.4129(2) 0.0412(9) Uani 1 1 d .
H1A H 0.5675 0.9807 -0.3522 0.049 Uiso 1 1 calc R
C2A C 0.6342(3) 1.0038(3) -0.4713(2) 0.0404(9) Uani 1 1 d .
C3A C 0.5917(3) 1.0172(3) -0.5637(2) 0.0398(9) Uani 1 1 d .
C4A C 0.7712(4) 1.0084(4) -0.4257(3) 0.0501(10) Uani 1 1 d .
C5A C 0.6732(4) 1.0319(4) -0.6428(3) 0.0454(9) Uani 1 1 d .
O1B O 1.5946(3) 1.4513(4) 0.2348(2) 0.0974(12) Uani 1 1 d .
O2B O 1.3744(3) 1.4204(3) 0.21220(16) 0.0632(8) Uani 1 1 d .
H2OB H 1.3623 1.4023 0.2746 0.050 Uiso 1 1 d .
O3B O 1.3479(3) 1.2751(3) -0.2195(2) 0.0851(11) Uani 1 1 d .
O4B O 1.1967(3) 1.2466(3) -0.1296(2) 0.0895(11) Uani 1 1 d .
H4OB H 1.125(3) 1.174(3) -0.187(2) 0.050 Uiso 1 1 d .
C1B C 1.4945(3) 1.4833(3) 0.0925(2) 0.0409(9) Uani 1 1 d .
C2B C 1.4016(3) 1.3973(3) 0.0189(2) 0.0402(9) Uani 1 1 d .
H2B H 1.3342 1.3280 0.0316 0.048 Uiso 1 1 calc R
C3B C 1.4058(3) 1.4109(3) -0.0729(2) 0.0413(9) Uani 1 1 d .
C4B C 1.4935(4) 1.4519(4) 0.1890(3) 0.0471(10) Uani 1 1 d .
C5B C 1.3153(4) 1.3054(4) -0.1490(2) 0.0446(10) 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
C21 N21 C22 106.2(3) . .
C23 N22 C21 107.3(3) . .
C23 N22 C28 124.1(3) . .
C21 N22 C28 128.6(3) . .
C11 N11 C12 108.3(3) . .
C11 N12 C13 106.8(3) . .
C11 N12 C18 128.4(3) . .
C13 N12 C18 124.7(3) . .
C1 N1 C5 116.1(4) . .
N1 C1 C2 123.5(4) . .
C3 C2 C1 118.9(4) . .
C3 C2 C11 121.5(3) . .
C1 C2 C11 119.4(4) . .
C4 C3 C2 118.5(3) . .
C5 C4 C3 118.1(4) . .
C5 C4 C21 123.8(4) . .
C3 C4 C21 118.1(3) . .
N1 C5 C4 124.8(4) . .
N11 C11 N12 111.0(3) . .
N11 C11 C2 123.9(3) . .
N12 C11 C2 125.1(3) . .
C13 C12 N11 106.9(3) . .
C13 C12 C17 121.0(3) . .
N11 C12 C17 132.0(3) . .
C12 C13 C14 121.3(4) . .
C12 C13 N12 107.0(3) . .
C14 C13 N12 131.7(4) . .
C15 C14 C13 117.1(4) . .
C14 C15 C16 121.7(4) . .
C17 C16 C15 122.0(4) . .
C16 C17 C12 116.9(4) . .
N21 C21 N22 111.2(3) . .
N21 C21 C4 124.4(3) . .
N22 C21 C4 124.4(3) . .
C27 C22 C23 121.2(3) . .
C27 C22 N21 130.4(3) . .
C23 C22 N21 108.5(3) . .
N22 C23 C22 106.8(3) . .
N22 C23 C24 131.7(3) . .
C22 C23 C24 121.4(4) . .
C25 C24 C23 116.5(4) . .
C24 C25 C26 122.1(4) . .
C27 C26 C25 121.7(4) . .
C26 C27 C22 117.0(3) . .
C3A C1A C2A 126.1(3) 2_674 .
C1A C2A C3A 116.8(3) . .
C1A C2A C4A 114.2(3) . .
C3A C2A C4A 129.0(3) . .
C1A C3A C2A 117.2(3) 2_674 .
C1A C3A C5A 115.1(3) 2_674 .
C2A C3A C5A 127.7(3) . .
O4A C4A O3A 118.9(4) . .
O4A C4A C2A 119.9(3) . .
O3A C4A C2A 121.2(3) . .
O2A C5A O1A 122.5(3) . .
O2A C5A C3A 117.7(3) . .
O1A C5A C3A 119.8(3) . .
C2B C1B C3B 118.6(3) . 2_885
C2B C1B C4B 118.5(3) . .
C3B C1B C4B 122.6(3) 2_885 .
C1B C2B C3B 122.3(3) . .
C2B C3B C1B 119.2(3) . 2_885
C2B C3B C5B 119.2(3) . .
C1B C3B C5B 121.3(3) 2_885 .
O1B C4B O2B 125.9(3) . .
O1B C4B C1B 120.6(3) . .
O2B C4B C1B 113.4(3) . .
O3B C5B O4B 122.4(4) . .
O3B C5B C3B 123.8(3) . .
O4B C5B C3B 113.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N21 C21 1.329(4) .
N21 C22 1.395(4) .
N22 C23 1.369(5) .
N22 C21 1.370(4) .
N22 C28 1.473(4) .
N11 C11 1.315(5) .
N11 C12 1.397(4) .
N12 C11 1.345(4) .
N12 C13 1.408(5) .
N12 C18 1.448(4) .
N1 C1 1.338(5) .
N1 C5 1.345(5) .
C1 C2 1.396(5) .
C2 C3 1.388(5) .
C2 C11 1.466(5) .
C3 C4 1.385(5) .
C4 C5 1.383(5) .
C4 C21 1.458(5) .
C12 C13 1.375(5) .
C12 C17 1.396(5) .
C13 C14 1.401(5) .
C14 C15 1.350(6) .
C15 C16 1.392(6) .
C16 C17 1.362(5) .
C22 C27 1.389(5) .
C22 C23 1.389(5) .
C23 C24 1.400(6) .
C24 C25 1.370(6) .
C25 C26 1.387(5) .
C26 C27 1.374(5) .
O1A C5A 1.256(4) .
O2A C5A 1.239(4) .
O3A C4A 1.273(4) .
O4A C4A 1.211(4) .
C1A C3A 1.376(5) 2_674
C1A C2A 1.383(4) .
C2A C3A 1.423(5) .
C2A C4A 1.508(5) .
C3A C1A 1.376(5) 2_674
C3A C5A 1.528(5) .
O1B C4B 1.198(4) .
O2B C4B 1.298(4) .
O3B C5B 1.179(4) .
O4B C5B 1.301(4) .
C1B C2B 1.385(5) .
C1B C3B 1.403(5) 2_885
C1B C4B 1.509(5) .
C2B C3B 1.384(4) .
C3B C1B 1.403(5) 2_885
C3B C5B 1.493(5) .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.500 1.000 331 135 ' '
