#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:41:09 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179671 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/24/4512422.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_4512422
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            'C77 H59 N10 O19'
_chemical_formula_weight         1429.35
_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                97.149(8)
_cell_angle_beta                 96.088(7)
_cell_angle_gamma                110.626(7)
_cell_formula_units_Z            1
_cell_length_a                   10.625(3)
_cell_length_b                   11.428(3)
_cell_length_c                   14.773(4)
_cell_measurement_reflns_used    20909
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      1.41
_cell_volume                     1643.9(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 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20909
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.41
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             743
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.431
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         6368
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.431
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0596
_refine_ls_shift/su_max          0.003
_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          0.1889
_refine_ls_wR_factor_ref         0.2005
_reflns_number_gt                4817
_reflns_number_total             6368
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg501380m_si_002.cif
_cod_data_source_block           7
_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        1643.8(7)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4512422
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
N1 N 1.4291(2) 0.3904(2) 0.37275(16) 0.0597(6) Uani 1 1 d .
C1 C 1.3784(3) 0.3187(2) 0.29010(18) 0.0520(6) Uani 1 1 d .
H1 H 1.2944 0.3149 0.2615 0.062 Uiso 1 1 calc R
C2 C 1.4429(2) 0.2488(2) 0.24339(16) 0.0419(5) Uani 1 1 d .
C3 C 1.5690(2) 0.2554(2) 0.28590(15) 0.0398(5) Uani 1 1 d .
H3 H 1.6164 0.2118 0.2562 0.048 Uiso 1 1 calc R
C4 C 1.6228(2) 0.3277(2) 0.37283(16) 0.0428(5) Uani 1 1 d .
C5 C 1.5484(3) 0.3927(3) 0.41307(18) 0.0541(7) Uani 1 1 d .
H5 H 1.5841 0.4409 0.4718 0.065 Uiso 1 1 calc R
N11 N 1.43009(18) 0.16384(17) 0.07740(13) 0.0399(4) Uani 1 1 d .
N12 N 1.24947(19) 0.07929(19) 0.14090(13) 0.0418(5) Uani 1 1 d .
H12N H 1.200(3) 0.062(2) 0.1861(19) 0.050 Uiso 1 1 d .
C11 C 1.3759(2) 0.1656(2) 0.15542(15) 0.0393(5) Uani 1 1 d .
C12 C 1.3319(2) 0.0721(2) 0.00858(15) 0.0398(5) Uani 1 1 d .
C13 C 1.2191(2) 0.0186(2) 0.05030(15) 0.0394(5) Uani 1 1 d .
C14 C 1.1008(3) -0.0768(2) -0.00042(17) 0.0489(6) Uani 1 1 d .
H14 H 1.0252 -0.1149 0.0270 0.059 Uiso 1 1 calc R
C15 C 1.1020(3) -0.1111(3) -0.09273(18) 0.0548(7) Uani 1 1 d .
H15 H 1.0246 -0.1730 -0.1288 0.066 Uiso 1 1 calc R
C16 C 1.2157(3) -0.0561(3) -0.13382(17) 0.0580(7) Uani 1 1 d .
H16 H 1.2118 -0.0820 -0.1966 0.070 Uiso 1 1 calc R
C17 C 1.3345(3) 0.0362(3) -0.08396(17) 0.0526(6) Uani 1 1 d .
H17 H 1.4113 0.0717 -0.1110 0.063 Uiso 1 1 calc R
C18 C 1.5651(2) 0.2459(2) 0.06333(19) 0.0517(6) Uani 1 1 d .
H18A H 1.5772 0.2239 0.0009 0.078 Uiso 1 1 calc R
H18B H 1.6338 0.2348 0.1052 0.078 Uiso 1 1 calc R
H18C H 1.5728 0.3330 0.0747 0.078 Uiso 1 1 calc R
N21 N 1.78367(19) 0.32278(18) 0.50766(12) 0.0429(5) Uani 1 1 d .
N22 N 1.85791(19) 0.34230(18) 0.37292(12) 0.0412(5) Uani 1 1 d .
C21 C 1.7551(2) 0.3327(2) 0.41783(15) 0.0391(5) Uani 1 1 d .
C22 C 1.9153(2) 0.3269(2) 0.52128(15) 0.0398(5) Uani 1 1 d .
C23 C 1.9616(2) 0.3388(2) 0.43664(15) 0.0385(5) Uani 1 1 d .
C24 C 2.0918(2) 0.3429(2) 0.42654(18) 0.0472(6) Uani 1 1 d .
H24 H 2.1236 0.3510 0.3705 0.057 Uiso 1 1 calc R
C25 C 2.1712(3) 0.3345(2) 0.50340(19) 0.0535(6) Uani 1 1 d .
H25 H 2.2583 0.3357 0.4990 0.064 Uiso 1 1 calc R
C26 C 2.1244(3) 0.3241(2) 0.58730(19) 0.0563(7) Uani 1 1 d .
H26 H 2.1821 0.3199 0.6377 0.068 Uiso 1 1 calc R
C27 C 1.9971(3) 0.3197(2) 0.59907(16) 0.0511(6) Uani 1 1 d .
H27 H 1.9668 0.3124 0.6556 0.061 Uiso 1 1 calc R
C28 C 1.6937(3) 0.3015(3) 0.57740(18) 0.0633(8) Uani 1 1 d .
H28A H 1.7436 0.2994 0.6349 0.095 Uiso 1 1 calc R
H28B H 1.6185 0.2221 0.5573 0.095 Uiso 1 1 calc R
H28C H 1.6600 0.3691 0.5858 0.095 Uiso 1 1 calc R
O1A O 2.30271(17) 0.7504(2) 0.13266(13) 0.0645(6) Uani 1 1 d .
H1AO H 2.351(3) 0.814(2) 0.1767(19) 0.050 Uiso 1 1 d .
O2A O 2.1344(2) 0.7452(2) 0.20739(16) 0.0954(9) Uani 1 1 d .
O3A O 2.0991(2) 0.4781(3) 0.23869(14) 0.0977(9) Uani 1 1 d .
O4A O 1.87452(17) 0.40385(18) 0.20969(12) 0.0551(5) Uani 1 1 d .
H4AO H 1.877(2) 0.378(2) 0.2701(19) 0.050 Uiso 1 1 d .
C1A C 2.0949(2) 0.6069(2) -0.01985(14) 0.0368(5) Uani 1 1 d .
H1A H 2.1601 0.6789 -0.0334 0.044 Uiso 1 1 calc R
C2A C 2.0893(2) 0.5934(2) 0.07187(14) 0.0351(5) Uani 1 1 d .
C3A C 1.9939(2) 0.4840(2) 0.09187(14) 0.0362(5) Uani 1 1 d .
C4A C 2.1775(2) 0.7017(2) 0.14595(15) 0.0421(5) Uani 1 1 d .
C5A C 1.9942(2) 0.4557(2) 0.18850(16) 0.0454(6) Uani 1 1 d .
O1B O 0.63140(19) -0.0227(3) 0.47556(14) 0.0832(7) Uani 1 1 d .
H1OB H 0.669(2) -0.013(2) 0.5523(19) 0.050 Uiso 1 1 d .
O2B O 0.71248(18) 0.0079(2) 0.34977(13) 0.0681(6) Uani 1 1 d .
O3B O 1.11490(17) 0.03615(19) 0.28032(11) 0.0578(5) Uani 1 1 d .
O4B O 1.29346(17) 0.0335(2) 0.36732(12) 0.0637(5) Uani 1 1 d .
C1B C 0.8667(2) -0.00230(19) 0.47384(14) 0.0330(5) Uani 1 1 d .
C2B C 0.9602(2) 0.0113(2) 0.41293(14) 0.0350(5) Uani 1 1 d .
H2B H 0.9326 0.0193 0.3529 0.042 Uiso 1 1 calc R
C3B C 1.0918(2) 0.01382(19) 0.43505(14) 0.0336(5) Uani 1 1 d .
C4B C 0.7293(2) -0.0052(2) 0.42966(16) 0.0426(5) Uani 1 1 d .
C5B C 1.1718(2) 0.0283(2) 0.35526(16) 0.0417(5) Uani 1 1 d .
O1W O 2.45137(18) 0.94865(17) 0.25421(13) 0.0524(5) Uani 1 1 d .
H1W H 2.529(3) 0.953(2) 0.2933(18) 0.050 Uiso 1 1 d .
H2W H 2.401(3) 0.971(2) 0.2921(19) 0.050 Uiso 1 1 d .
O101 O 0.7896(5) 0.6726(5) -0.0778(4) 0.1029(17) Uani 0.50 1 d P
C108 C 0.7005(7) 0.5695(6) -0.0876(5) 0.0706(17) Uani 0.50 1 d P
H108 H 0.7042 0.5104 -0.1356 0.085 Uiso 0.50 1 calc PR
C101 C 0.6090(5) 0.5306(4) -0.0465(5) 0.1156(18) Uani 1 1 d .
C102 C 0.4814(5) 0.4387(4) -0.0907(4) 0.1151(19) Uani 1 1 d .
C103 C 0.3665(6) 0.4082(4) -0.0423(5) 0.132(2) Uani 1 1 d .
C104 C 0.2380(6) 0.3193(5) -0.0867(6) 0.155(3) Uani 1 1 d .
H104 H 0.1652 0.3038 -0.0541 0.186 Uiso 1 1 calc R
C105 C 0.2153(12) 0.2563(8) -0.1728(8) 0.209(5) Uani 1 1 d .
H105 H 0.1284 0.2009 -0.2005 0.251 Uiso 1 1 calc R
C106 C 0.3295(10) 0.2767(6) -0.2213(5) 0.186(5) Uani 1 1 d .
H106 H 0.3194 0.2280 -0.2788 0.223 Uiso 1 1 calc R
C107 C 0.4565(6) 0.3709(4) -0.1814(4) 0.149(3) Uani 1 1 d .
H107 H 0.5268 0.3891 -0.2162 0.178 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
C1 N1 C5 117.0(2) . .
N1 C1 C2 124.0(2) . .
C1 C2 C3 117.9(2) . .
C1 C2 C11 120.6(2) . .
C3 C2 C11 121.4(2) . .
C4 C3 C2 119.1(2) . .
C3 C4 C5 117.8(2) . .
C3 C4 C21 118.8(2) . .
C5 C4 C21 123.4(2) . .
N1 C5 C4 124.1(2) . .
C11 N11 C12 107.91(18) . .
C11 N11 C18 127.2(2) . .
C12 N11 C18 124.84(19) . .
C11 N12 C13 108.53(19) . .
N12 C11 N11 109.9(2) . .
N12 C11 C2 124.2(2) . .
N11 C11 C2 125.9(2) . .
C13 C12 C17 122.8(2) . .
C13 C12 N11 106.14(19) . .
C17 C12 N11 131.0(2) . .
N12 C13 C12 107.5(2) . .
N12 C13 C14 131.7(2) . .
C12 C13 C14 120.8(2) . .
C15 C14 C13 116.6(2) . .
C14 C15 C16 122.0(2) . .
C17 C16 C15 122.0(2) . .
C16 C17 C12 115.8(2) . .
C21 N21 C22 106.48(18) . .
C21 N21 C28 128.9(2) . .
C22 N21 C28 124.4(2) . .
C21 N22 C23 105.90(19) . .
N22 C21 N21 112.7(2) . .
N22 C21 C4 122.6(2) . .
N21 C21 C4 124.7(2) . .
N21 C22 C23 106.53(19) . .
N21 C22 C27 131.7(2) . .
C23 C22 C27 121.8(2) . .
C24 C23 N22 130.6(2) . .
C24 C23 C22 121.0(2) . .
N22 C23 C22 108.4(2) . .
C25 C24 C23 116.8(2) . .
C24 C25 C26 121.6(3) . .
C27 C26 C25 122.8(2) . .
C26 C27 C22 116.1(2) . .
C3A C1A C2A 121.80(19) 2_965 .
C1A C2A C3A 118.97(19) . .
C1A C2A C4A 118.74(19) . .
C3A C2A C4A 122.07(18) . .
C1A C3A C2A 119.21(19) 2_965 .
C1A C3A C5A 118.88(19) 2_965 .
C2A C3A C5A 121.61(19) . .
O2A C4A O1A 123.1(2) . .
O2A C4A C2A 123.0(2) . .
O1A C4A C2A 113.6(2) . .
O3A C5A O4A 124.8(2) . .
O3A C5A C3A 120.8(2) . .
O4A C5A C3A 114.44(19) . .
C2B C1B C3B 117.75(18) . 2_756
C2B C1B C4B 113.29(18) . .
C3B C1B C4B 128.95(19) 2_756 .
C1B C2B C3B 124.9(2) . .
C2B C3B C1B 117.31(19) . 2_756
C2B C3B C5B 114.06(19) . .
C1B C3B C5B 128.63(19) 2_756 .
O2B C4B O1B 119.6(2) . .
O2B C4B C1B 119.7(2) . .
O1B C4B C1B 120.6(2) . .
O3B C5B O4B 122.2(2) . .
O3B C5B C3B 117.9(2) . .
O4B C5B C3B 119.8(2) . .
O101 C108 C101 130.8(8) . .
C108 C101 C103 113.9(6) . 2_665
C108 C101 C102 121.6(7) . .
C103 C101 C102 124.1(6) 2_665 .
C107 C102 C101 124.5(7) . .
C107 C102 C103 115.5(5) . .
C101 C102 C103 120.0(5) . .
C101 C103 C104 123.7(8) 2_665 .
C101 C103 C102 115.9(5) 2_665 .
C104 C103 C102 120.4(7) . .
C105 C104 C103 123.6(10) . .
C104 C105 C106 117.9(10) . .
C107 C106 C105 119.6(8) . .
C106 C107 C102 122.6(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.324(3) .
N1 C5 1.331(3) .
C1 C2 1.391(3) .
C2 C3 1.390(3) .
C2 C11 1.456(3) .
C3 C4 1.381(3) .
C4 C5 1.391(3) .
C4 C21 1.468(3) .
N11 C11 1.343(3) .
N11 C12 1.400(3) .
N11 C18 1.464(3) .
N12 C11 1.332(3) .
N12 C13 1.377(3) .
C12 C13 1.387(3) .
C12 C17 1.384(3) .
C13 C14 1.401(3) .
C14 C15 1.374(4) .
C15 C16 1.392(4) .
C16 C17 1.386(4) .
N21 C21 1.357(3) .
N21 C22 1.375(3) .
N21 C28 1.463(3) .
N22 C21 1.317(3) .
N22 C23 1.386(3) .
C22 C23 1.397(3) .
C22 C27 1.395(3) .
C23 C24 1.392(3) .
C24 C25 1.375(3) .
C25 C26 1.387(4) .
C26 C27 1.366(4) .
O1A C4A 1.295(3) .
O2A C4A 1.190(3) .
O3A C5A 1.198(3) .
O4A C5A 1.290(3) .
C1A C3A 1.387(3) 2_965
C1A C2A 1.388(3) .
C2A C3A 1.393(3) .
C2A C4A 1.495(3) .
C3A C1A 1.387(3) 2_965
C3A C5A 1.502(3) .
O1B C4B 1.272(3) .
O2B C4B 1.210(3) .
O3B C5B 1.233(3) .
O4B C5B 1.265(3) .
C1B C2B 1.391(3) .
C1B C3B 1.408(3) 2_756
C1B C4B 1.521(3) .
C2B C3B 1.392(3) .
C3B C1B 1.408(3) 2_756
C3B C5B 1.517(3) .
O101 C108 1.203(8) .
C108 C101 1.183(8) .
C101 C103 1.360(8) 2_665
C101 C102 1.416(5) .
C102 C107 1.410(8) .
C102 C103 1.439(8) .
C103 C101 1.360(8) 2_665
C103 C104 1.411(6) .
C104 C105 1.334(11) .
C105 C106 1.438(13) .
C106 C107 1.405(9) .
