#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:41:09 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179671 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/24/4512419.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_4512419
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            'C78 H60 N10 O18'
_chemical_formula_weight         1425.36
_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                96.553(8)
_cell_angle_beta                 97.070(8)
_cell_angle_gamma                111.233(8)
_cell_formula_units_Z            1
_cell_length_a                   10.741(3)
_cell_length_b                   11.454(3)
_cell_length_c                   14.658(4)
_cell_measurement_reflns_used    21035
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      1.42
_cell_volume                     1643.4(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0552
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21035
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'Off white'
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             742
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     496
_refine_ls_number_reflns         6350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0662
_refine_ls_shift/su_max          0.058
_refine_ls_shift/su_mean         0.002
_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          0.1684
_refine_ls_wR_factor_ref         0.1937
_reflns_number_gt                3723
_reflns_number_total             6350
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg501380m_si_002.cif
_cod_data_source_block           4
_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        1643.5(7)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4512419
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 0.9505(2) 0.9569(2) 0.25417(16) 0.0495(6) Uani 1 1 d .
H1W H 0.903(3) 0.976(3) 0.294(2) 0.050 Uiso 1 1 d .
H2W H 1.021(4) 0.956(3) 0.284(2) 0.050 Uiso 1 1 d .
N21 N 1.3631(2) 1.3481(2) 0.37714(16) 0.0397(6) Uani 1 1 d .
N22 N 1.2899(2) 1.3197(2) 0.51194(16) 0.0405(6) Uani 1 1 d .
N11 N 0.7510(2) 1.0820(3) 0.14136(17) 0.0416(7) Uani 1 1 d .
H11N H 0.698(3) 1.059(3) 0.185(2) 0.050 Uiso 1 1 d .
N12 N 0.9300(2) 1.1644(2) 0.07805(17) 0.0392(6) Uani 1 1 d .
N1 N 0.9315(3) 1.3828(3) 0.37937(19) 0.0531(8) Uani 1 1 d .
C1 C 0.8802(3) 1.3131(3) 0.2953(2) 0.0484(9) Uani 1 1 d .
H1 H 0.7948 1.3064 0.2674 0.058 Uiso 1 1 calc R
C2 C 0.9460(3) 1.2489(3) 0.2458(2) 0.0406(7) Uani 1 1 d .
C3 C 1.0738(3) 1.2589(3) 0.2886(2) 0.0387(7) Uani 1 1 d .
H3 H 1.1220 1.2191 0.2575 0.046 Uiso 1 1 calc R
C4 C 1.1281(3) 1.3281(3) 0.3771(2) 0.0390(7) Uani 1 1 d .
C5 C 1.0534(3) 1.3888(3) 0.4200(2) 0.0498(9) Uani 1 1 d .
H5 H 1.0899 1.4357 0.4798 0.060 Uiso 1 1 calc R
C11 C 0.8777(3) 1.1670(3) 0.1563(2) 0.0377(7) Uani 1 1 d .
C12 C 0.7191(3) 1.0213(3) 0.0494(2) 0.0404(8) Uani 1 1 d .
C13 C 0.8320(3) 1.0744(3) 0.0093(2) 0.0402(7) Uani 1 1 d .
C14 C 0.8324(4) 1.0368(3) -0.0847(2) 0.0519(9) Uani 1 1 d .
H14 H 0.9086 1.0717 -0.1117 0.062 Uiso 1 1 calc R
C15 C 0.7138(4) 0.9452(4) -0.1354(2) 0.0588(10) Uani 1 1 d .
H15 H 0.7089 0.9192 -0.1987 0.071 Uiso 1 1 calc R
C16 C 0.6009(4) 0.8906(4) -0.0941(2) 0.0591(10) Uani 1 1 d .
H16 H 0.5232 0.8282 -0.1306 0.071 Uiso 1 1 calc R
C17 C 0.6005(3) 0.9256(3) -0.0016(2) 0.0510(9) Uani 1 1 d .
H17 H 0.5254 0.8877 0.0257 0.061 Uiso 1 1 calc R
C18 C 1.0662(3) 1.2461(3) 0.0647(2) 0.0520(9) Uani 1 1 d .
H18A H 1.0771 1.2241 0.0018 0.078 Uiso 1 1 calc R
H18B H 1.1339 1.2338 0.1073 0.078 Uiso 1 1 calc R
H18C H 1.0763 1.3335 0.0762 0.078 Uiso 1 1 calc R
C21 C 1.2600(3) 1.3339(3) 0.42236(19) 0.0366(7) Uani 1 1 d .
C22 C 1.4669(3) 1.3423(3) 0.44131(19) 0.0368(7) Uani 1 1 d .
C23 C 1.4217(3) 1.3250(3) 0.52605(19) 0.0363(7) Uani 1 1 d .
C24 C 1.5028(3) 1.3134(3) 0.6037(2) 0.0463(8) Uani 1 1 d .
H24 H 1.4726 1.3021 0.6601 0.056 Uiso 1 1 calc R
C25 C 1.6289(3) 1.3196(3) 0.5920(2) 0.0515(9) Uani 1 1 d .
H25 H 1.6867 1.3135 0.6423 0.062 Uiso 1 1 calc R
C26 C 1.6745(3) 1.3349(3) 0.5076(2) 0.0490(8) Uani 1 1 d .
H26 H 1.7606 1.3366 0.5029 0.059 Uiso 1 1 calc R
C27 C 1.5956(3) 1.3474(3) 0.4310(2) 0.0454(8) Uani 1 1 d .
H27 H 1.6269 1.3588 0.3750 0.054 Uiso 1 1 calc R
C28 C 1.2005(4) 1.2921(4) 0.5811(2) 0.0596(10) Uani 1 1 d .
H28A H 1.2505 1.2875 0.6387 0.089 Uiso 1 1 calc R
H28B H 1.1259 1.2124 0.5586 0.089 Uiso 1 1 calc R
H28C H 1.1665 1.3584 0.5915 0.089 Uiso 1 1 calc R
O1A O 0.7907(2) 1.0325(3) 0.36936(16) 0.0597(7) Uani 1 1 d .
O2A O 0.6159(2) 1.0415(3) 0.28017(15) 0.0586(7) Uani 1 1 d .
O3A O 0.8674(2) 1.0266(3) 0.52949(18) 0.0794(10) Uani 1 1 d .
H3OA H 0.832(3) 1.025(3) 0.453(2) 0.050 Uiso 1 1 d .
O4A O 0.7911(2) 1.0070(3) 0.65748(17) 0.0784(9) Uani 1 1 d .
C1A C 0.5407(3) 0.9908(3) 0.58875(19) 0.0338(7) Uani 1 1 d .
H1A H 0.5689 0.9849 0.6500 0.041 Uiso 1 1 calc R
C2A C 0.6334(3) 1.0057(3) 0.52853(19) 0.0325(7) Uani 1 1 d .
C3A C 0.5915(3) 1.0157(3) 0.43578(19) 0.0327(7) Uani 1 1 d .
C4A C 0.7710(3) 1.0133(3) 0.5754(2) 0.0433(8) Uani 1 1 d .
C5A C 0.6714(3) 1.0303(3) 0.3557(2) 0.0417(8) Uani 1 1 d .
O1B O 1.5962(2) 1.4823(3) 0.24324(17) 0.0796(9) Uani 1 1 d .
O2B O 1.3722(2) 1.4132(2) 0.21234(15) 0.0541(7) Uani 1 1 d .
H2OB H 1.373(3) 1.385(3) 0.263(2) 0.050 Uiso 1 1 d .
O3B O 1.3672(3) 1.2510(3) -0.20800(19) 0.0855(10) Uani 1 1 d .
O4B O 1.2032(2) 1.2352(2) -0.12777(16) 0.0549(7) Uani 1 1 d .
H4BO H 1.152(3) 1.166(3) -0.177(2) 0.050 Uiso 1 1 d .
C1B C 1.4925(3) 1.4887(3) 0.09398(19) 0.0358(7) Uani 1 1 d .
C2B C 1.4061(3) 1.3938(3) 0.02166(19) 0.0368(7) Uani 1 1 d .
H2B H 1.3414 1.3223 0.0363 0.044 Uiso 1 1 calc R
C3B C 1.4124(3) 1.4018(3) -0.07182(19) 0.0351(7) Uani 1 1 d .
C4B C 1.4919(3) 1.4629(3) 0.1919(2) 0.0407(8) Uani 1 1 d .
C5B C 1.3260(3) 1.2903(3) -0.1441(2) 0.0417(8) Uani 1 1 d .
C100 C -0.0782(8) 0.5584(8) 0.1840(6) 0.132(3) Uani 1 1 d .
H100 H -0.1481 0.5365 0.2184 0.158 Uiso 1 1 calc R
C101 C 0.0495(9) 0.6563(7) 0.2245(5) 0.125(2) Uani 1 1 d .
H101 H 0.0591 0.6979 0.2848 0.150 Uiso 1 1 calc R
C102 C 0.1583(8) 0.6928(6) 0.1809(5) 0.1121(19) Uani 1 1 d .
H102 H 0.2406 0.7567 0.2097 0.135 Uiso 1 1 calc R
C103 C 0.1387(6) 0.6261(6) 0.0859(5) 0.1061(19) Uani 1 1 d .
C104 C 0.0151(4) 0.5334(4) 0.0463(3) 0.0720(12) Uani 1 1 d .
C105 C -0.0977(7) 0.4993(6) 0.0989(5) 0.102(2) Uani 1 1 d .
C106 C 0.2425(6) 0.6564(7) 0.0356(6) 0.116(2) Uani 1 1 d .
H106 H 0.3263 0.7185 0.0636 0.140 Uiso 1 1 calc R
C107 C 0.2274(6) 0.6000(6) -0.0518(6) 0.103(2) Uani 1 1 d .
H107 H 0.3001 0.6240 -0.0835 0.124 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_1
_geom_angle_site_symmetry_3
C21 N21 C22 105.7(2) . .
C21 N22 C23 107.1(2) . .
C21 N22 C28 128.5(3) . .
C23 N22 C28 124.2(3) . .
C11 N11 C12 108.2(3) . .
C11 N12 C13 108.2(2) . .
C11 N12 C18 126.9(3) . .
C13 N12 C18 124.9(3) . .
C1 N1 C5 117.3(3) . .
N1 C1 C2 124.2(3) . .
C1 C2 C3 117.4(3) . .
C1 C2 C11 120.4(3) . .
C3 C2 C11 122.0(3) . .
C4 C3 C2 119.6(3) . .
C3 C4 C5 118.1(3) . .
C3 C4 C21 119.0(3) . .
C5 C4 C21 122.9(3) . .
N1 C5 C4 123.3(3) . .
N11 C11 N12 109.9(3) . .
N11 C11 C2 123.5(3) . .
N12 C11 C2 126.6(3) . .
C13 C12 N11 107.0(3) . .
C13 C12 C17 121.6(3) . .
N11 C12 C17 131.5(3) . .
N12 C13 C12 106.8(3) . .
N12 C13 C14 131.5(3) . .
C12 C13 C14 121.7(3) . .
C15 C14 C13 116.5(3) . .
C14 C15 C16 121.5(3) . .
C17 C16 C15 122.3(3) . .
C16 C17 C12 116.4(3) . .
N21 C21 N22 112.3(3) . .
N21 C21 C4 122.6(3) . .
N22 C21 C4 125.0(3) . .
C27 C22 N21 130.5(3) . .
C27 C22 C23 120.8(3) . .
N21 C22 C23 108.7(3) . .
N22 C23 C24 131.7(3) . .
N22 C23 C22 106.2(2) . .
C24 C23 C22 122.1(3) . .
C25 C24 C23 116.0(3) . .
C24 C25 C26 122.5(3) . .
C27 C26 C25 121.8(3) . .
C26 C27 C22 116.8(3) . .
C2A C1A C3A 124.9(3) . 2_676
C1A C2A C3A 117.8(2) . .
C1A C2A C4A 113.2(2) . .
C3A C2A C4A 129.0(3) . .
C1A C3A C2A 117.3(2) 2_676 .
C1A C3A C5A 114.1(2) 2_676 .
C2A C3A C5A 128.5(3) . .
O4A C4A O3A 118.8(3) . .
O4A C4A C2A 120.3(3) . .
O3A C4A C2A 120.9(3) . .
O2A C5A O1A 122.9(3) . .
O2A C5A C3A 117.7(3) . .
O1A C5A C3A 119.4(3) . .
C2B C1B C3B 118.7(3) . 2_885
C2B C1B C4B 118.4(3) . .
C3B C1B C4B 122.5(2) 2_885 .
C1B C2B C3B 122.6(3) . .
C2B C3B C1B 118.7(3) . 2_885
C2B C3B C5B 118.8(3) . .
C1B C3B C5B 122.2(3) 2_885 .
O1B C4B O2B 124.8(3) . .
O1B C4B C1B 120.7(3) . .
O2B C4B C1B 114.4(3) . .
O3B C5B O4B 123.4(3) . .
O3B C5B C3B 123.1(3) . .
O4B C5B C3B 113.4(3) . .
C105 C100 C101 120.2(7) . .
C102 C101 C100 124.3(8) . .
C101 C102 C103 116.2(7) . .
C106 C103 C104 119.6(7) . .
C106 C103 C102 120.7(7) . .
C104 C103 C102 119.6(6) . .
C103 C104 C104 123.8(6) . 2_565
C103 C104 C105 120.6(5) . .
C104 C104 C105 115.6(6) 2_565 .
C100 C105 C107 123.3(7) . 2_565
C100 C105 C104 119.1(7) . .
C107 C105 C104 117.6(5) 2_565 .
C107 C106 C103 122.4(7) . .
C106 C107 C105 120.9(6) . 2_565
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 1.394(4) .
N22 C21 1.355(4) .
N22 C23 1.383(4) .
N22 C28 1.464(4) .
N11 C11 1.329(4) .
N11 C12 1.384(4) .
N12 C11 1.340(4) .
N12 C13 1.379(4) .
N12 C18 1.474(4) .
N1 C1 1.323(4) .
N1 C5 1.345(4) .
C1 C2 1.395(4) .
C2 C3 1.396(4) .
C2 C11 1.457(4) .
C3 C4 1.377(4) .
C4 C5 1.397(4) .
C4 C21 1.464(4) .
C12 C13 1.382(4) .
C12 C17 1.397(4) .
C13 C14 1.397(4) .
C14 C15 1.376(5) .
C15 C16 1.396(5) .
C16 C17 1.369(5) .
C22 C27 1.390(4) .
C22 C23 1.398(4) .
C23 C24 1.395(4) .
C24 C25 1.364(5) .
C25 C26 1.392(5) .
C26 C27 1.375(4) .
O1A C5A 1.263(4) .
O2A C5A 1.235(4) .
O3A C4A 1.276(4) .
O4A C4A 1.210(4) .
C1A C2A 1.389(4) .
C1A C3A 1.393(4) 2_676
C2A C3A 1.410(4) .
C2A C4A 1.519(4) .
C3A C1A 1.393(4) 2_676
C3A C5A 1.526(4) .
O1B C4B 1.202(4) .
O2B C4B 1.292(4) .
O3B C5B 1.195(4) .
O4B C5B 1.305(4) .
C1B C2B 1.389(4) .
C1B C3B 1.403(4) 2_885
C1B C4B 1.498(4) .
C2B C3B 1.392(4) .
C3B C1B 1.403(4) 2_885
C3B C5B 1.485(4) .
C100 C105 1.303(9) .
C100 C101 1.423(9) .
C101 C102 1.357(8) .
C102 C103 1.461(9) .
C103 C106 1.374(8) .
C103 C104 1.370(7) .
C104 C104 1.416(9) 2_565
C104 C105 1.474(7) .
C105 C107 1.465(8) 2_565
C106 C107 1.329(8) .
C107 C105 1.465(8) 2_565
