#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:41:22 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257900 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/91/7059192.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_7059192
loop_
_publ_author_name
'Xu, Juan'
'Du, Rongkai'
'Wu, Lvying'
'Zhang, Xianrui'
'Guan, Su'
'Zhang, Lei'
'Ning, Lifeng'
'Li, Shan'
_publ_section_title
;
 Azilsartan piperazine salt solvate and monohydrate: preparation, crystal
 structure, enhanced solubility and oral bioavailability
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              852
_journal_page_last               860
_journal_paper_doi               10.1039/C9NJ05042F
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C25 H18 N4 O5, C4 H12 N2, H2 O'
_chemical_formula_sum            'C29 H32 N6 O6'
_chemical_formula_weight         560.61
_chemical_name_common            'Azilsartan-Piperazine-water '
_chemical_name_systematic
; 
 '2-Ethoxy-1-[[2??-(4,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid?\/c2-ethoxy-3-((2'-(5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)Methyl)-3H-benzozimidazole-4-carboxylic acid:Piperazine:water(1:1:1) ' 
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc1phhxl
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-07-24 deposited with the CCDC.	2019-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.634(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3028(14)
_cell_length_b                   14.3949(18)
_cell_length_c                   16.962(2)
_cell_measurement_reflns_used    15759
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.71
_cell_volume                     2735.3(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0627
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12981
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9903
_exptl_absorpt_correction_T_min  0.9884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.745
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         4778
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.0637
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1067P)²+0.1099P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1648
_refine_ls_wR_factor_ref         0.2017
_reflns_number_gt                2578
_reflns_number_total             4778
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9nj05042f1.cif
_cod_data_source_block           53
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7059191--7059193.cif.

 Adding full bibliography for 7059191--7059193.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7059192
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.29405(18) 0.27518(15) -0.02147(12) 0.0628(5) Uani 1 1 d U
C2 C 0.40483(17) 0.19426(13) 0.06227(11) 0.0537(5) Uani 1 1 d U
C3 C 0.50182(17) 0.16457(13) 0.12479(11) 0.0533(6) Uani 1 1 d .
C4 C 0.56345(19) 0.08292(14) 0.11129(14) 0.0702(7) Uani 1 1 d .
H4 H 0.5411 0.0500 0.0645 0.084 Uiso 1 1 calc R
C5 C 0.6559(2) 0.04975(16) 0.16484(14) 0.0812(8) Uani 1 1 d .
H5 H 0.6958 -0.0045 0.1547 0.097 Uiso 1 1 calc R
C6 C 0.6876(2) 0.09917(17) 0.23401(15) 0.0819(8) Uani 1 1 d .
C7 C 0.62805(19) 0.17892(15) 0.24910(13) 0.0687(7) Uani 1 1 d .
H7 H 0.6506 0.2103 0.2966 0.082 Uiso 1 1 calc R
C8 C 0.53484(16) 0.21446(13) 0.19552(11) 0.0534(6) Uani 1 1 d .
C9 C 0.47550(16) 0.30120(13) 0.21736(10) 0.0492(5) Uani 1 1 d .
C10 C 0.35270(17) 0.31098(13) 0.20978(11) 0.0540(6) Uani 1 1 d .
H10 H 0.3045 0.2631 0.1870 0.065 Uiso 1 1 calc R
C11 C 0.30031(16) 0.38958(13) 0.23495(11) 0.0528(6) Uani 1 1 d .
H11 H 0.2175 0.3940 0.2284 0.063 Uiso 1 1 calc R
C12 C 0.36832(16) 0.46271(13) 0.27005(10) 0.0482(5) Uani 1 1 d .
C13 C 0.49046(17) 0.45401(14) 0.27668(11) 0.0572(6) Uani 1 1 d .
H13 H 0.5385 0.5023 0.2989 0.069 Uiso 1 1 calc R
C14 C 0.54292(17) 0.37496(14) 0.25100(12) 0.0584(6) Uani 1 1 d .
H14 H 0.6257 0.3711 0.2564 0.070 Uiso 1 1 calc R
C15 C 0.30757(17) 0.54482(13) 0.30266(12) 0.0550(6) Uani 1 1 d .
H15A H 0.2313 0.5548 0.2703 0.066 Uiso 1 1 calc R
H15B H 0.2920 0.5303 0.3562 0.066 Uiso 1 1 calc R
C16 C 0.6589(3) 0.5874(2) 0.4927(2) 0.1508(13) Uani 1 1 d DU
H16A H 0.6417 0.5229 0.4822 0.226 Uiso 1 1 calc R
H16B H 0.7140 0.5932 0.5406 0.226 Uiso 1 1 calc R
H16C H 0.6936 0.6138 0.4491 0.226 Uiso 1 1 calc R
C17 C 0.5501(2) 0.6358(2) 0.50193(17) 0.1210(8) Uani 1 1 d DU
H17A H 0.5623 0.7025 0.5016 0.145 Uiso 1 1 calc R
H17B H 0.5217 0.6185 0.5514 0.145 Uiso 1 1 calc R
C18 C 0.46048(18) 0.65573(14) 0.36648(12) 0.0609(6) Uani 1 1 d .
C19 C 0.39408(15) 0.69019(12) 0.24218(11) 0.0461(5) Uani 1 1 d .
C20 C 0.48888(16) 0.74846(13) 0.27324(11) 0.0520(6) Uani 1 1 d U
C21 C 0.53247(19) 0.81495(15) 0.22704(13) 0.0674(7) Uani 1 1 d U
H21 H 0.5952 0.8534 0.2477 0.081 Uiso 1 1 calc R
C22 C 0.4811(2) 0.82337(15) 0.14929(13) 0.0692(7) Uani 1 1 d .
H22 H 0.5099 0.8677 0.1168 0.083 Uiso 1 1 calc R
C23 C 0.38663(18) 0.76673(13) 0.11832(13) 0.0609(6) Uani 1 1 d .
H23 H 0.3542 0.7740 0.0654 0.073 Uiso 1 1 calc R
C24 C 0.33887(16) 0.69934(12) 0.16409(11) 0.0491(5) Uani 1 1 d .
C25 C 0.22860(17) 0.64697(13) 0.12723(12) 0.0569(5) Uani 1 1 d U
C26 C 0.4924(2) 0.53644(15) 0.07755(12) 0.0706(7) Uani 1 1 d .
H26A H 0.5183 0.5814 0.1189 0.085 Uiso 1 1 calc R
H26B H 0.4333 0.4965 0.0968 0.085 Uiso 1 1 calc R
C27 C 0.40473(19) 0.51993(14) -0.06134(12) 0.0647(7) Uani 1 1 d .
H27A H 0.3418 0.4792 -0.0483 0.078 Uiso 1 1 calc R
H27B H 0.3741 0.5544 -0.1088 0.078 Uiso 1 1 calc R
C28 C 0.94824(19) 0.57650(15) -0.04549(14) 0.0751(7) Uani 1 1 d .
H28A H 0.9548 0.6391 -0.0657 0.090 Uiso 1 1 calc R
H28B H 0.8687 0.5537 -0.0642 0.090 Uiso 1 1 calc R
C29 C 0.9617(2) 0.48434(15) 0.07690(15) 0.0789(8) Uani 1 1 d .
H29A H 0.8826 0.4581 0.0634 0.095 Uiso 1 1 calc R
H29B H 0.9787 0.4880 0.1344 0.095 Uiso 1 1 calc R
H1 H 1.0436(19) 0.6086(14) 0.0622(12) 0.085(7) Uiso 1 1 d .
H2 H 0.900(2) 0.6133(16) 0.0565(16) 0.113(8) Uiso 1 1 d .
H3 H 0.5034(15) 0.6191(11) -0.0087(10) 0.053(5) Uiso 1 1 d .
H6 H 0.741(2) 0.0838(17) 0.2743(14) 0.104(8) Uiso 1 1 d .
H8 H 0.3714(6) 0.6105(10) 0.0178(9) 0.098(8) Uiso 1 1 d D
N1 N 0.39322(13) 0.28018(11) 0.03000(9) 0.0542(5) Uani 1 1 d .
N2 N 0.32479(17) 0.13431(13) 0.03487(13) 0.0900(6) Uani 1 1 d U
N3 N 0.37688(13) 0.63044(10) 0.30476(9) 0.0530(5) Uani 1 1 d .
N4 N 0.52865(15) 0.72520(11) 0.35232(10) 0.0626(5) Uani 1 1 d .
N5 N 0.43741(15) 0.58585(11) 0.00516(10) 0.0586(5) Uani 1 1 d D
N6 N 0.96552(16) 0.57871(12) 0.04217(12) 0.0756(6) Uani 1 1 d .
O1 O 0.24201(13) 0.33597(11) -0.06605(9) 0.0823(5) Uani 1 1 d .
O2 O 0.24837(14) 0.18850(12) -0.02219(10) 0.0948(5) Uani 1 1 d U
O3 O 0.46439(15) 0.60675(11) 0.43286(9) 0.0869(5) Uani 1 1 d U
O4 O 0.14706(12) 0.63274(11) 0.16581(10) 0.0812(5) Uani 1 1 d U
O5 O 0.22608(13) 0.62487(11) 0.05500(9) 0.0784(5) Uani 1 1 d .
O6 O 0.75960(16) 0.80271(14) 0.39649(12) 0.1152(7) Uani 1 1 d D
H6WA H 0.6856(6) 0.7862(15) 0.390(2) 0.173 Uiso 1 1 d D
H6WB H 0.744(3) 0.7789(11) 0.3495(5) 0.173 Uiso 1 1 d 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
O1 C1 N1 130.35(19) . .
O1 C1 O2 119.50(17) . .
N1 C1 O2 110.15(17) . .
N2 C2 N1 116.10(17) . .
N2 C2 C3 118.73(17) . .
N1 C2 C3 125.16(16) . .
C4 C3 C8 119.15(17) . .
C4 C3 C2 117.47(17) . .
C8 C3 C2 123.39(17) . .
C5 C4 C3 122.3(2) . .
C4 C5 C6 118.2(2) . .
C7 C6 C5 120.8(2) . .
C6 C7 C8 122.2(2) . .
C7 C8 C3 117.45(18) . .
C7 C8 C9 118.20(17) . .
C3 C8 C9 124.35(16) . .
C10 C9 C14 116.77(17) . .
C10 C9 C8 122.83(16) . .
C14 C9 C8 120.30(16) . .
C11 C10 C9 121.61(17) . .
C10 C11 C12 121.41(17) . .
C13 C12 C11 117.26(17) . .
C13 C12 C15 122.81(16) . .
C11 C12 C15 119.85(16) . .
C12 C13 C14 121.18(18) . .
C13 C14 C9 121.75(18) . .
N3 C15 C12 113.70(16) . .
C16 C17 O3 104.8(3) . .
N4 C18 O3 127.67(18) . .
N4 C18 N3 115.44(18) . .
O3 C18 N3 116.88(18) . .
C24 C19 N3 133.57(16) . .
C24 C19 C20 121.47(17) . .
N3 C19 C20 104.96(15) . .
C21 C20 N4 128.49(17) . .
C21 C20 C19 121.10(18) . .
N4 C20 C19 110.38(16) . .
C20 C21 C22 118.19(19) . .
C21 C22 C23 121.1(2) . .
C22 C23 C24 122.15(19) . .
C19 C24 C23 115.92(16) . .
C19 C24 C25 125.73(17) . .
C23 C24 C25 118.24(17) . .
O4 C25 O5 123.95(18) . .
O4 C25 C24 120.08(18) . .
O5 C25 C24 115.87(18) . .
C27 C26 N5 111.34(18) 3_665 .
C26 C27 N5 111.80(17) 3_665 .
N6 C28 C29 111.55(17) . 3_765
N6 C29 C28 109.8(2) . 3_765
C1 N1 C2 104.17(16) . .
C2 N2 O2 102.07(16) . .
C18 N3 C19 105.44(15) . .
C18 N3 C15 124.04(16) . .
C19 N3 C15 128.98(15) . .
C18 N4 C20 103.77(15) . .
C26 N5 C27 110.97(15) . .
C28 N6 C29 111.95(17) . .
C1 O2 N2 107.49(15) . .
C18 O3 C17 117.86(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.251(2) .
C1 N1 1.328(2) .
C1 O2 1.350(3) .
C2 N2 1.291(3) .
C2 N1 1.352(2) .
C2 C3 1.483(3) .
C3 C4 1.401(3) .
C3 C8 1.405(3) .
C4 C5 1.376(3) .
C5 C6 1.378(3) .
C6 C7 1.372(3) .
C7 C8 1.394(3) .
C8 C9 1.487(3) .
C9 C10 1.384(3) .
C9 C14 1.385(3) .
C10 C11 1.371(3) .
C11 C12 1.390(2) .
C12 C13 1.376(3) .
C12 C15 1.509(3) .
C13 C14 1.380(3) .
C15 N3 1.458(2) .
C16 C17 1.440(4) .
C17 O3 1.478(3) .
C18 N4 1.304(3) .
C18 O3 1.324(3) .
C18 N3 1.363(2) .
C19 C24 1.393(3) .
C19 N3 1.400(2) .
C19 C20 1.407(2) .
C20 C21 1.369(3) .
C20 N4 1.398(2) .
C21 C22 1.374(3) .
C22 C23 1.390(3) .
C23 C24 1.395(3) .
C24 C25 1.518(3) .
C25 O4 1.217(3) .
C25 O5 1.262(2) .
C26 C27 1.474(3) 3_665
C26 N5 1.482(3) .
C27 C26 1.474(3) 3_665
C27 N5 1.483(3) .
C28 N6 1.474(3) .
C28 C29 1.493(3) 3_765
C29 N6 1.484(3) .
C29 C28 1.493(3) 3_765
N2 O2 1.439(2) .
