#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:41:22 +0200 (mar 06 de oct de 2020) $
#$Revision: 257900 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/91/7059191.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_7059191
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 H19 N4 O5, 1/2 C4 H12 N2, C2 H6 O'
_chemical_formula_sum            'C29 H31 N5 O6'
_chemical_formula_weight         545.59
_chemical_name_common            'Azilsartan-Piperazine-ethanol '
_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:ethanol(1:0.5:1) ' 
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_block_doi                 10.5517/ccdc.csd.cc1phhwk
_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                82.781(8)
_cell_angle_beta                 85.788(7)
_cell_angle_gamma                89.002(7)
_cell_formula_units_Z            2
_cell_length_a                   5.7924(4)
_cell_length_b                   13.4728(13)
_cell_length_c                   17.3811(18)
_cell_measurement_reflns_used    10975
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      2.97
_cell_volume                     1342.0(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0691
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9179
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9699
_exptl_absorpt_correction_T_min  0.9671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         4720
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0570
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0742P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1672
_reflns_number_gt                2983
_reflns_number_total             4720
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9nj05042f1.cif
_cod_data_source_block           exp_2847
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' 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-1
_cod_database_code               7059191
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
C1 C 1.4618(6) 0.1423(3) 0.4754(2) 0.0566(9) Uani 1 1 d .
C2 C 1.1859(5) 0.1430(2) 0.39432(17) 0.0427(7) Uani 1 1 d .
C3 C 1.0161(5) 0.1028(2) 0.34837(18) 0.0443(7) Uani 1 1 d .
C4 C 0.9716(5) 0.0002(2) 0.3627(2) 0.0586(9) Uani 1 1 d .
H4 H 1.0541 -0.0397 0.3990 0.070 Uiso 1 1 calc R
C5 C 0.8093(6) -0.0427(3) 0.3244(2) 0.0687(10) Uani 1 1 d .
H5 H 0.7841 -0.1113 0.3338 0.082 Uiso 1 1 calc R
C6 C 0.6840(6) 0.0162(3) 0.2720(2) 0.0729(11) Uani 1 1 d .
H6 H 0.5713 -0.0124 0.2466 0.087 Uiso 1 1 calc R
C7 C 0.7239(5) 0.1175(3) 0.2569(2) 0.0629(10) Uani 1 1 d .
H7 H 0.6372 0.1564 0.2213 0.075 Uiso 1 1 calc R
C8 C 0.8912(5) 0.1629(2) 0.29373(18) 0.0445(7) Uani 1 1 d .
C9 C 0.9312(4) 0.2725(2) 0.27142(16) 0.0388(7) Uani 1 1 d .
C10 C 0.7612(4) 0.3418(2) 0.28699(16) 0.0390(7) Uani 1 1 d .
H10 H 0.6200 0.3200 0.3117 0.047 Uiso 1 1 calc R
C11 C 0.7974(4) 0.4425(2) 0.26650(16) 0.0387(7) Uani 1 1 d .
H11 H 0.6805 0.4877 0.2777 0.046 Uiso 1 1 calc R
C12 C 1.0050(4) 0.4776(2) 0.22943(15) 0.0319(6) Uani 1 1 d .
C13 C 1.1713(4) 0.4082(2) 0.21113(16) 0.0403(7) Uani 1 1 d .
H13 H 1.3105 0.4300 0.1849 0.048 Uiso 1 1 calc R
C14 C 1.1347(5) 0.3066(2) 0.23120(18) 0.0451(8) Uani 1 1 d .
H14 H 1.2480 0.2610 0.2175 0.054 Uiso 1 1 calc R
C15 C 1.0575(4) 0.5871(2) 0.21248(16) 0.0375(7) Uani 1 1 d .
H15A H 1.0754 0.6131 0.2613 0.045 Uiso 1 1 calc R
H15B H 1.2043 0.5951 0.1818 0.045 Uiso 1 1 calc R
C16 C 1.2932(6) 0.6014(3) -0.0606(2) 0.0718(11) Uani 1 1 d .
H16A H 1.4250 0.6275 -0.0397 0.108 Uiso 1 1 calc R
H16B H 1.3069 0.6155 -0.1163 0.108 Uiso 1 1 calc R
H16C H 1.2861 0.5303 -0.0460 0.108 Uiso 1 1 calc R
C17 C 1.0799(6) 0.6488(3) -0.02978(18) 0.0687(11) Uani 1 1 d .
H17A H 1.0883 0.7209 -0.0423 0.082 Uiso 1 1 calc R
H17B H 0.9463 0.6256 -0.0527 0.082 Uiso 1 1 calc R
C18 C 0.8878(5) 0.6641(2) 0.09203(17) 0.0428(7) Uani 1 1 d .
C19 C 0.6908(4) 0.7005(2) 0.19812(16) 0.0353(6) Uani 1 1 d .
C20 C 0.5924(4) 0.7446(2) 0.13076(17) 0.0419(7) Uani 1 1 d .
C21 C 0.3930(5) 0.8020(2) 0.13577(19) 0.0487(8) Uani 1 1 d .
H21 H 0.3269 0.8315 0.0912 0.058 Uiso 1 1 calc R
C22 C 0.2952(5) 0.8140(2) 0.2084(2) 0.0491(8) Uani 1 1 d .
H22 H 0.1619 0.8530 0.2130 0.059 Uiso 1 1 calc R
C23 C 0.3911(4) 0.7695(2) 0.27481(18) 0.0419(7) Uani 1 1 d .
H23 H 0.3184 0.7784 0.3230 0.050 Uiso 1 1 calc R
C24 C 0.5916(4) 0.7119(2) 0.27228(17) 0.0360(7) Uani 1 1 d .
C25 C 0.6907(4) 0.6698(2) 0.34693(16) 0.0362(7) Uani 1 1 d .
C26 C -0.1057(4) 0.4186(2) 0.46996(17) 0.0443(7) Uani 1 1 d .
H26A H -0.2273 0.4523 0.4409 0.053 Uiso 1 1 calc R
H26B H -0.1122 0.3477 0.4653 0.053 Uiso 1 1 calc R
C27 C 0.1250(4) 0.4590(2) 0.43718(17) 0.0441(8) Uani 1 1 d .
H27A H 0.2470 0.4213 0.4633 0.053 Uiso 1 1 calc R
H27B H 0.1451 0.4515 0.3823 0.053 Uiso 1 1 calc R
C28 C 0.6669(17) 0.9173(5) 0.9166(5) 0.182(4) Uani 1 1 d D
H28A H 0.5853 0.9464 0.9592 0.218 Uiso 1 1 calc R
H28B H 0.6143 0.9538 0.8693 0.218 Uiso 1 1 calc R
C29 C 0.8996(14) 0.9439(7) 0.9181(8) 0.272(6) Uani 1 1 d D
H29A H 0.9132 1.0153 0.9087 0.408 Uiso 1 1 calc R
H29B H 0.9914 0.9142 0.8786 0.408 Uiso 1 1 calc R
H29C H 0.9535 0.9203 0.9682 0.408 Uiso 1 1 calc R
H1 H 1.341(7) 0.0186(15) 0.448(3) 0.118(17) Uiso 1 1 d D
H6A H 0.652(13) 0.792(6) 0.957(4) 0.26(4) Uiso 1 1 d D
N1 N 1.3296(5) 0.0840(2) 0.43947(17) 0.0598(8) Uani 1 1 d D
N2 N 1.2179(4) 0.2364(2) 0.39942(16) 0.0559(7) Uani 1 1 d .
N3 N 0.8834(3) 0.64697(17) 0.17128(13) 0.0358(6) Uani 1 1 d .
N4 N 0.7215(4) 0.7212(2) 0.06431(14) 0.0480(7) Uani 1 1 d .
N5 N 0.1424(3) 0.56585(18) 0.44731(13) 0.0409(6) Uani 1 1 d .
H5A H 0.2833 0.5885 0.4285 0.049 Uiso 1 1 calc R
H5B H 0.0360 0.6013 0.4200 0.049 Uiso 1 1 calc R
O1 O 1.6124(5) 0.12189(19) 0.51905(16) 0.0837(9) Uani 1 1 d .
O2 O 1.3986(4) 0.23716(16) 0.45195(13) 0.0577(6) Uani 1 1 d .
O3 O 1.0596(3) 0.62193(17) 0.05305(11) 0.0534(6) Uani 1 1 d .
O4 O 0.8934(3) 0.69294(17) 0.35624(12) 0.0524(6) Uani 1 1 d .
O5 O 0.5710(3) 0.61337(17) 0.39593(12) 0.0581(6) Uani 1 1 d .
O6 O 0.5825(8) 0.8259(4) 0.9199(2) 0.1271(13) Uani 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
O1 C1 O2 122.5(3) .
O1 C1 N1 131.4(3) .
O2 C1 N1 106.1(3) .
N2 C2 N1 111.0(3) .
N2 C2 C3 125.9(3) .
N1 C2 C3 123.1(3) .
C4 C3 C8 119.3(3) .
C4 C3 C2 117.6(3) .
C8 C3 C2 123.0(3) .
C5 C4 C3 121.3(3) .
C4 C5 C6 119.4(3) .
C5 C6 C7 120.4(3) .
C6 C7 C8 121.4(3) .
C7 C8 C3 118.1(3) .
C7 C8 C9 118.1(3) .
C3 C8 C9 123.8(3) .
C14 C9 C10 118.3(3) .
C14 C9 C8 120.8(2) .
C10 C9 C8 120.9(2) .
C11 C10 C9 121.0(3) .
C10 C11 C12 121.1(2) .
C13 C12 C11 117.9(3) .
C13 C12 C15 119.7(2) .
C11 C12 C15 122.3(2) .
C12 C13 C14 121.1(2) .
C9 C14 C13 120.5(3) .
N3 C15 C12 114.8(2) .
O3 C17 C16 107.8(3) .
N4 C18 O3 128.1(3) .
N4 C18 N3 115.3(3) .
O3 C18 N3 116.6(2) .
C24 C19 C20 121.7(2) .
C24 C19 N3 133.3(2) .
C20 C19 N3 104.9(2) .
C21 C20 N4 128.6(3) .
C21 C20 C19 120.6(3) .
N4 C20 C19 110.8(2) .
C22 C21 C20 118.1(3) .
C21 C22 C23 121.3(3) .
C22 C23 C24 122.5(3) .
C23 C24 C19 115.9(3) .
C23 C24 C25 119.3(3) .
C19 C24 C25 124.8(2) .
O5 C25 O4 123.2(3) .
O5 C25 C24 119.6(2) .
O4 C25 C24 117.3(2) .
N5 C26 C27 109.9(2) 2_566
N5 C27 C26 110.5(2) .
O6 C28 C29 127.3(8) .
C1 N1 C2 109.1(3) .
C2 N2 O2 104.8(2) .
C18 N3 C19 105.3(2) .
C18 N3 C15 123.1(2) .
C19 N3 C15 131.6(2) .
C18 N4 C20 103.6(2) .
C26 N5 C27 111.5(2) 2_566
C1 O2 N2 109.0(2) .
C18 O3 C17 116.7(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.203(4) .
C1 O2 1.345(4) .
C1 N1 1.345(4) .
C2 N2 1.290(4) .
C2 N1 1.363(4) .
C2 C3 1.463(4) .
C3 C4 1.399(4) .
C3 C8 1.403(4) .
C4 C5 1.367(4) .
C5 C6 1.372(5) .
C6 C7 1.378(5) .
C7 C8 1.390(4) .
C8 C9 1.497(4) .
C9 C14 1.380(4) .
C9 C10 1.380(4) .
C10 C11 1.374(4) .
C11 C12 1.384(4) .
C12 C13 1.379(3) .
C12 C15 1.500(4) .
C13 C14 1.386(4) .
C15 N3 1.454(3) .
C16 C17 1.477(4) .
C17 O3 1.436(4) .
C18 N4 1.304(3) .
C18 O3 1.323(3) .
C18 N3 1.366(4) .
C19 C24 1.398(4) .
C19 C20 1.400(4) .
C19 N3 1.401(3) .
C20 C21 1.382(4) .
C20 N4 1.396(4) .
C21 C22 1.373(4) .
C22 C23 1.381(4) .
C23 C24 1.386(4) .
C24 C25 1.500(4) .
C25 O5 1.246(3) .
C25 O4 1.247(3) .
C26 N5 1.479(3) 2_566
C26 C27 1.497(4) .
C27 N5 1.478(4) .
C28 O6 1.325(8) .
C28 C29 1.404(7) .
N2 O2 1.440(3) .
N5 C26 1.479(3) 2_566
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N2 C2 C3 C4 -166.6(3) . .
N1 C2 C3 C4 12.0(4) . .
N2 C2 C3 C8 10.7(5) . .
N1 C2 C3 C8 -170.8(3) . .
C8 C3 C4 C5 0.2(5) . .
C2 C3 C4 C5 177.5(3) . .
C3 C4 C5 C6 -1.4(5) . .
C4 C5 C6 C7 1.2(6) . .
C5 C6 C7 C8 0.1(6) . .
C6 C7 C8 C3 -1.3(5) . .
C6 C7 C8 C9 177.3(3) . .
C4 C3 C8 C7 1.1(4) . .
C2 C3 C8 C7 -176.1(3) . .
C4 C3 C8 C9 -177.4(3) . .
C2 C3 C8 C9 5.4(4) . .
C7 C8 C9 C14 -111.0(3) . .
C3 C8 C9 C14 67.5(4) . .
C7 C8 C9 C10 65.6(4) . .
C3 C8 C9 C10 -115.9(3) . .
C14 C9 C10 C11 -3.2(4) . .
C8 C9 C10 C11 -179.9(3) . .
C9 C10 C11 C12 0.2(4) . .
C10 C11 C12 C13 2.3(4) . .
C10 C11 C12 C15 -174.6(2) . .
C11 C12 C13 C14 -1.8(4) . .
C15 C12 C13 C14 175.2(3) . .
C10 C9 C14 C13 3.7(4) . .
C8 C9 C14 C13 -179.6(3) . .
C12 C13 C14 C9 -1.2(4) . .
C13 C12 C15 N3 130.5(3) . .
C11 C12 C15 N3 -52.6(3) . .
C24 C19 C20 C21 0.5(4) . .
N3 C19 C20 C21 178.5(3) . .
C24 C19 C20 N4 -179.2(2) . .
N3 C19 C20 N4 -1.2(3) . .
N4 C20 C21 C22 179.6(3) . .
C19 C20 C21 C22 -0.1(4) . .
C20 C21 C22 C23 -0.7(5) . .
C21 C22 C23 C24 1.1(5) . .
C22 C23 C24 C19 -0.7(4) . .
C22 C23 C24 C25 177.3(3) . .
C20 C19 C24 C23 -0.1(4) . .
N3 C19 C24 C23 -177.5(3) . .
C20 C19 C24 C25 -178.0(3) . .
N3 C19 C24 C25 4.7(5) . .
C23 C24 C25 O5 58.7(4) . .
C19 C24 C25 O5 -123.5(3) . .
C23 C24 C25 O4 -122.0(3) . .
C19 C24 C25 O4 55.8(4) . .
N5 C26 C27 N5 -56.5(3) 2_566 .
O1 C1 N1 C2 -178.7(4) . .
O2 C1 N1 C2 -0.1(4) . .
N2 C2 N1 C1 -0.2(4) . .
C3 C2 N1 C1 -178.9(3) . .
N1 C2 N2 O2 0.4(3) . .
C3 C2 N2 O2 179.0(3) . .
N4 C18 N3 C19 -0.6(3) . .
O3 C18 N3 C19 178.9(2) . .
N4 C18 N3 C15 -178.6(2) . .
O3 C18 N3 C15 0.9(4) . .
C24 C19 N3 C18 178.7(3) . .
C20 C19 N3 C18 1.0(3) . .
C24 C19 N3 C15 -3.5(5) . .
C20 C19 N3 C15 178.8(3) . .
C12 C15 N3 C18 -89.7(3) . .
C12 C15 N3 C19 92.9(3) . .
O3 C18 N4 C20 -179.6(3) . .
N3 C18 N4 C20 -0.2(3) . .
C21 C20 N4 C18 -178.8(3) . .
C19 C20 N4 C18 0.9(3) . .
C26 C27 N5 C26 57.5(3) . 2_566
O1 C1 O2 N2 179.1(3) . .
N1 C1 O2 N2 0.4(4) . .
C2 N2 O2 C1 -0.5(3) . .
N4 C18 O3 C17 6.2(5) . .
N3 C18 O3 C17 -173.2(3) . .
C16 C17 O3 C18 174.8(3) . .
