#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:41:09 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179671 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/24/4512421.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_4512421
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            'C76 H60 N10 O18'
_chemical_formula_weight         1401.34
_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                96.914(10)
_cell_angle_beta                 96.252(10)
_cell_angle_gamma                110.223(10)
_cell_formula_units_Z            1
_cell_length_a                   10.651(4)
_cell_length_b                   11.362(4)
_cell_length_c                   14.732(5)
_cell_measurement_reflns_used    20569
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.74
_cell_measurement_theta_min      1.41
_cell_volume                     1638.9(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 0.955
_diffrn_measured_fraction_theta_max 0.955
_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  0.1289
_diffrn_reflns_av_sigmaI/netI    0.2492
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20569
_diffrn_reflns_theta_full        26.74
_diffrn_reflns_theta_max         26.74
_diffrn_reflns_theta_min         1.41
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             730
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_platon_squeeze_details
;
;
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.850
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         6652
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.850
_refine_ls_R_factor_all          0.1908
_refine_ls_R_factor_gt           0.0765
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.001
_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          0.2057
_refine_ls_wR_factor_ref         0.2571
_reflns_number_gt                2722
_reflns_number_total             6652
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg501380m_si_002.cif
_cod_data_source_block           6
_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_sg_symbol_H-M      P-1
_cod_database_code               4512421
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 2.0499(3) 1.0524(3) 0.2462(2) 0.0558(9) Uani 1 1 d .
H1WO H 2.097(4) 1.023(4) 0.195(3) 0.050 Uiso 1 1 d .
H2WO H 1.971(4) 1.047(4) 0.219(3) 0.050 Uiso 1 1 d .
N1 N 1.0653(4) 0.6083(4) 0.1223(3) 0.0662(12) Uani 1 1 d .
C1 C 0.9460(4) 0.6075(5) 0.0826(3) 0.0601(13) Uani 1 1 d .
H1 H 0.9103 0.5605 0.0234 0.072 Uiso 1 1 calc R
C2 C 0.8717(4) 0.6720(4) 0.1235(3) 0.0476(11) Uani 1 1 d .
C3 C 0.9274(4) 0.7437(4) 0.2120(3) 0.0468(11) Uani 1 1 d .
H3 H 0.8811 0.7883 0.2423 0.056 Uiso 1 1 calc R
C4 C 1.0503(4) 0.7478(4) 0.2537(3) 0.0440(10) Uani 1 1 d .
C5 C 1.1162(4) 0.6791(5) 0.2070(3) 0.0582(13) Uani 1 1 d .
H5 H 1.1998 0.6824 0.2357 0.070 Uiso 1 1 calc R
N11 N 0.6364(3) 0.6586(3) 0.1242(2) 0.0477(9) Uani 1 1 d .
N12 N 0.7104(3) 0.6776(3) -0.0107(2) 0.0489(9) Uani 1 1 d .
C11 C 0.7395(4) 0.6672(4) 0.0788(2) 0.0423(10) Uani 1 1 d .
C12 C 0.5784(4) 0.6747(4) -0.0248(3) 0.0469(11) Uani 1 1 d .
C13 C 0.5333(4) 0.6622(4) 0.0608(3) 0.0451(10) Uani 1 1 d .
C14 C 0.4040(4) 0.6569(4) 0.0698(3) 0.0527(12) Uani 1 1 d .
H14 H 0.3720 0.6478 0.1257 0.063 Uiso 1 1 calc R
C15 C 0.3249(5) 0.6653(5) -0.0068(3) 0.0587(13) Uani 1 1 d .
H15 H 0.2382 0.6643 -0.0019 0.070 Uiso 1 1 calc R
C16 C 0.3694(5) 0.6754(5) -0.0913(3) 0.0601(13) Uani 1 1 d .
H16 H 0.3111 0.6788 -0.1418 0.072 Uiso 1 1 calc R
C17 C 0.4966(5) 0.6803(5) -0.1026(3) 0.0571(13) Uani 1 1 d .
H17 H 0.5266 0.6871 -0.1594 0.068 Uiso 1 1 calc R
C18 C 0.8011(5) 0.7004(6) -0.0808(3) 0.0700(15) Uani 1 1 d .
H18A H 0.8911 0.7544 -0.0514 0.105 Uiso 1 1 calc R
H18B H 0.7687 0.7410 -0.1266 0.105 Uiso 1 1 calc R
H18C H 0.8025 0.6207 -0.1100 0.105 Uiso 1 1 calc R
N21 N 1.2430(3) 0.9142(4) 0.3567(2) 0.0485(9) Uani 1 1 d .
H21 H 1.2963 0.9289 0.3162 0.058 Uiso 1 1 calc R
N22 N 1.0641(3) 0.8313(4) 0.4201(2) 0.0486(9) Uani 1 1 d .
C21 C 1.1181(4) 0.8299(4) 0.3418(3) 0.0457(11) Uani 1 1 d .
C22 C 1.1615(4) 0.9206(5) 0.4886(3) 0.0488(11) Uani 1 1 d .
C23 C 1.2748(4) 0.9755(4) 0.4481(3) 0.0465(11) Uani 1 1 d .
C24 C 1.3929(5) 1.0691(5) 0.4981(3) 0.0580(13) Uani 1 1 d .
H24 H 1.4680 1.1066 0.4704 0.070 Uiso 1 1 calc R
C25 C 1.3921(6) 1.1029(5) 0.5913(3) 0.0690(15) Uani 1 1 d .
H25 H 1.4689 1.1645 0.6277 0.083 Uiso 1 1 calc R
C26 C 1.2786(6) 1.0466(6) 0.6321(3) 0.0728(16) Uani 1 1 d .
H26 H 1.2836 1.0700 0.6955 0.087 Uiso 1 1 calc R
C27 C 1.1605(5) 0.9585(5) 0.5828(3) 0.0623(13) Uani 1 1 d .
H27 H 1.0838 0.9256 0.6100 0.075 Uiso 1 1 calc R
C28 C 0.9296(4) 0.7508(5) 0.4343(3) 0.0581(13) Uani 1 1 d .
H28A H 0.8699 0.7975 0.4315 0.087 Uiso 1 1 calc R
H28B H 0.9360 0.7252 0.4938 0.087 Uiso 1 1 calc R
H28C H 0.8945 0.6767 0.3868 0.087 Uiso 1 1 calc R
O11A O 1.8693(3) 1.0261(5) 0.0280(2) 0.0909(14) Uani 1 1 d .
H1OA H 1.844(4) 1.041(4) -0.045(3) 0.050 Uiso 1 1 d .
O12A O 1.7923(3) 1.0129(4) 0.1562(2) 0.0904(14) Uani 1 1 d .
O13A O 1.3809(3) 0.9577(3) 0.2186(2) 0.0654(10) Uani 1 1 d .
O14A O 1.2076(3) 0.9690(4) 0.1316(2) 0.0695(11) Uani 1 1 d .
C11A C 1.6339(3) 1.0071(4) 0.0282(2) 0.0371(9) Uani 1 1 d .
C12A C 1.5407(3) 0.9916(4) 0.0879(2) 0.0391(10) Uani 1 1 d .
H12A H 1.5686 0.9849 0.1485 0.047 Uiso 1 1 calc R
C13A C 1.4082(3) 0.9852(4) 0.0645(3) 0.0387(10) Uani 1 1 d .
C14A C 1.7725(4) 1.0144(5) 0.0742(3) 0.0545(12) Uani 1 1 d .
C15A C 1.3253(4) 0.9712(4) 0.1431(3) 0.0444(10) Uani 1 1 d .
O11B O 0.2006(3) 0.2460(4) 0.3709(2) 0.0727(12) Uani 1 1 d .
H1B1 H 0.154(4) 0.188(4) 0.333(3) 0.050 Uiso 1 1 d .
O12B O 0.3644(4) 0.2598(4) 0.2902(2) 0.0980(15) Uani 1 1 d .
O13B O 0.3994(3) 0.5318(4) 0.2631(2) 0.0953(14) Uani 1 1 d .
O14B O 0.6220(3) 0.5942(3) 0.28786(19) 0.0621(10) Uani 1 1 d .
H11 H 0.634(4) 0.614(4) 0.216(3) 0.075 Uiso 1 1 d .
C11B C 0.4104(4) 0.4071(4) 0.4289(2) 0.0421(10) Uani 1 1 d .
C12B C 0.5053(4) 0.5170(4) 0.4071(2) 0.0409(10) Uani 1 1 d .
C13B C 0.5937(4) 0.6071(4) 0.4791(3) 0.0438(10) Uani 1 1 d .
H13B H 0.6579 0.6794 0.4654 0.053 Uiso 1 1 calc R
C14B C 0.3233(4) 0.2987(5) 0.3545(3) 0.0505(12) Uani 1 1 d .
C15B C 0.5042(4) 0.5459(4) 0.3108(3) 0.0506(12) 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
C1 N1 C5 116.6(4) . .
N1 C1 C2 124.5(4) . .
C1 C2 C3 117.1(4) . .
C1 C2 C11 123.2(4) . .
C3 C2 C11 119.6(4) . .
C4 C3 C2 119.6(4) . .
C3 C4 C5 118.8(4) . .
C3 C4 C21 121.7(4) . .
C5 C4 C21 119.4(4) . .
N1 C5 C4 123.4(4) . .
C11 N11 C13 106.2(3) . .
C11 N12 C12 107.0(3) . .
C11 N12 C18 128.6(4) . .
C12 N12 C18 124.2(3) . .
N11 C11 N12 112.3(3) . .
N11 C11 C2 123.0(3) . .
N12 C11 C2 124.6(3) . .
C17 C12 N12 132.0(4) . .
C17 C12 C13 122.3(4) . .
N12 C12 C13 105.7(3) . .
N11 C13 C14 131.2(4) . .
N11 C13 C12 108.8(4) . .
C14 C13 C12 120.0(4) . .
C15 C14 C13 117.4(4) . .
C14 C15 C16 122.1(5) . .
C17 C16 C15 121.9(4) . .
C16 C17 C12 116.2(4) . .
C21 N21 C23 109.3(3) . .
C21 N22 C22 107.8(3) . .
C21 N22 C28 127.4(4) . .
C22 N22 C28 124.7(3) . .
N21 C21 N22 109.8(4) . .
N21 C21 C4 124.7(3) . .
N22 C21 C4 125.5(4) . .
N22 C22 C23 107.2(3) . .
N22 C22 C27 131.8(4) . .
C23 C22 C27 121.0(4) . .
N21 C23 C22 106.0(4) . .
N21 C23 C24 131.7(4) . .
C22 C23 C24 122.3(4) . .
C25 C24 C23 116.1(5) . .
C24 C25 C26 121.5(5) . .
C27 C26 C25 122.7(5) . .
C26 C27 C22 116.2(5) . .
C12A C11A C13A 117.9(3) . 2_875
C12A C11A C14A 113.1(3) . .
C13A C11A C14A 128.9(3) 2_875 .
C11A C12A C13A 124.9(3) . .
C12A C13A C11A 117.1(3) . 2_875
C12A C13A C15A 115.3(3) . .
C11A C13A C15A 127.5(3) 2_875 .
O12A C14A O11A 119.2(4) . .
O12A C14A C11A 119.7(4) . .
O11A C14A C11A 121.0(4) . .
O14A C15A O13A 122.1(3) . .
O14A C15A C13A 121.3(3) . .
O13A C15A C13A 116.5(3) . .
C13B C11B C12B 119.7(4) 2_666 .
C13B C11B C14B 118.9(4) 2_666 .
C12B C11B C14B 121.1(3) . .
C13B C12B C11B 118.2(3) . .
C13B C12B C15B 119.0(4) . .
C11B C12B C15B 122.4(3) . .
C12B C13B C11B 122.1(4) . 2_666
O12B C14B O11B 123.3(4) . .
O12B C14B C11B 123.5(4) . .
O11B C14B C11B 113.1(4) . .
O13B C15B O14B 124.5(4) . .
O13B C15B C12B 120.5(4) . .
O14B C15B C12B 114.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.337(6) .
N1 C5 1.344(6) .
C1 C2 1.387(6) .
C2 C3 1.399(6) .
C2 C11 1.469(6) .
C3 C4 1.366(6) .
C4 C5 1.390(6) .
C4 C21 1.455(6) .
N11 C11 1.329(5) .
N11 C13 1.377(5) .
N12 C11 1.349(5) .
N12 C12 1.387(5) .
N12 C18 1.474(5) .
C12 C17 1.384(6) .
C12 C13 1.403(6) .
C13 C14 1.378(6) .
C14 C15 1.366(6) .
C15 C16 1.383(6) .
C16 C17 1.366(6) .
N21 C21 1.319(5) .
N21 C23 1.386(5) .
N22 C21 1.344(5) .
N22 C22 1.386(5) .
N22 C28 1.463(5) .
C22 C23 1.388(6) .
C22 C27 1.405(6) .
C23 C24 1.393(6) .
C24 C25 1.383(6) .
C25 C26 1.395(7) .
C26 C27 1.367(7) .
O11A C14A 1.275(5) .
O12A C14A 1.207(5) .
O13A C15A 1.254(5) .
O14A C15A 1.237(4) .
C11A C12A 1.377(5) .
C11A C13A 1.412(5) 2_875
C11A C14A 1.526(5) .
C12A C13A 1.390(5) .
C13A C11A 1.412(5) 2_875
C13A C15A 1.523(5) .
O11B C14B 1.299(5) .
O12B C14B 1.187(5) .
O13B C15B 1.201(5) .
O14B C15B 1.285(5) .
C11B C13B 1.388(5) 2_666
C11B C12B 1.407(5) .
C11B C14B 1.497(6) .
C12B C13B 1.384(5) .
C12B C15B 1.494(5) .
C13B C11B 1.388(5) 2_666
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 0.500 326 105 ' '
