# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_2847
_audit_block_doi                 10.5517/ccdc.csd.cc1phhwk
_database_code_depnum_ccdc_archive 'CCDC 1564039'
_audit_update_record             
;
2017-07-24 deposited with the CCDC.	2019-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_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) ' 
;
_chemical_name_common            'Azilsartan-Piperazine-ethanol '
_chemical_melting_point          ?
_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

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7924(4)
_cell_length_b                   13.4728(13)
_cell_length_c                   17.3811(18)
_cell_angle_alpha                82.781(8)
_cell_angle_beta                 85.788(7)
_cell_angle_gamma                89.002(7)
_cell_volume                     1342.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    10975
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      25.02

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9671
_exptl_absorpt_correction_T_max  0.9699
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9179
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0691
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4720
_reflns_number_gt                2983
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0742P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4720
_refine_ls_number_parameters     372
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1672
_refine_ls_wR_factor_gt          0.1404
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.043
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_53
_audit_block_doi                 10.5517/ccdc.csd.cc1phhxl
_database_code_depnum_ccdc_archive 'CCDC 1564040'
_audit_update_record             
;
2017-07-24 deposited with the CCDC.	2019-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_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) ' 
;
_chemical_name_common            'Azilsartan-Piperazine-water '
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H18 N4 O5, C4 H12 N2, H2 O'
_chemical_formula_sum            'C29 H32 N6 O6'
_chemical_formula_weight         560.61

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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'

_cell_length_a                   11.3028(14)
_cell_length_b                   14.3949(18)
_cell_length_c                   16.962(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.634(2)
_cell_angle_gamma                90.00
_cell_volume                     2735.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    15759
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      25.03

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9884
_exptl_absorpt_correction_T_max  0.9903
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12981
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_sigmaI/netI    0.0627
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         25.02
_reflns_number_total             4778
_reflns_number_gt                2578
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1067P)²+0.1099P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4778
_refine_ls_number_parameters     397
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.2017
_refine_ls_wR_factor_gt          0.1648
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
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 . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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) . ?

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
_geom_angle_publ_flag
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) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.745
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.048
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_2292
_audit_block_doi                 10.5517/ccdc.csd.cc1phhym
_database_code_depnum_ccdc_archive 'CCDC 1564041'
_audit_update_record             
;
2017-07-24 deposited with the CCDC.	2019-12-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_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:methanol(1:0.5:1) '
;
_chemical_name_common            'Azilsartan-Piperazine-methanol '
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H19 N4 O5, 1/2 C4 H12 N2, C H4 O'
_chemical_formula_sum            'C28 H29 N5 O6'
_chemical_formula_weight         531.56

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7804(4)
_cell_length_b                   13.3882(10)
_cell_length_c                   17.3847(12)
_cell_angle_alpha                82.750(6)
_cell_angle_beta                 85.718(5)
_cell_angle_gamma                88.040(6)
_cell_volume                     1330.49(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    10455
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      25.03

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9684
_exptl_absorpt_correction_T_max  0.9738
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8782
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         25.03
_reflns_number_total             4688
_reflns_number_gt                3526
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0778P)²+0.1962P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4688
_refine_ls_number_parameters     359
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1481
_refine_ls_wR_factor_gt          0.1325
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.4652(5) 0.14360(17) 0.47360(16) 0.0574(7) Uani 1 1 d . . .
C2 C 1.1914(4) 0.14495(15) 0.39208(13) 0.0418(5) Uani 1 1 d . . .
C3 C 1.0211(4) 0.10490(15) 0.34595(14) 0.0426(5) Uani 1 1 d . . .
C4 C 0.9753(4) 0.00196(17) 0.36107(16) 0.0560(7) Uani 1 1 d . . .
H4 H 1.0562 -0.0384 0.3981 0.067 Uiso 1 1 calc R . .
C5 C 0.8137(5) -0.04022(19) 0.32231(18) 0.0676(8) Uani 1 1 d . . .
H5 H 0.7852 -0.1087 0.3330 0.081 Uiso 1 1 calc R . .
C6 C 0.6947(5) 0.0184(2) 0.2680(2) 0.0732(9) Uani 1 1 d . . .
H6 H 0.5846 -0.0102 0.2418 0.088 Uiso 1 1 calc R . .
C7 C 0.7364(5) 0.12012(19) 0.25173(17) 0.0632(7) Uani 1 1 d . . .
H7 H 0.6528 0.1591 0.2147 0.076 Uiso 1 1 calc R . .
C8 C 0.9003(4) 0.16531(15) 0.28940(14) 0.0434(5) Uani 1 1 d . . .
C9 C 0.9384(3) 0.27540(15) 0.26748(12) 0.0372(5) Uani 1 1 d . . .
C10 C 0.7653(4) 0.34454(15) 0.28472(12) 0.0375(5) Uani 1 1 d . . .
H10 H 0.6250 0.3222 0.3096 0.045 Uiso 1 1 calc R . .
C11 C 0.7989(3) 0.44644(15) 0.26537(12) 0.0363(5) Uani 1 1 d . . .
H11 H 0.6810 0.4921 0.2775 0.044 Uiso 1 1 calc R . .
C12 C 1.0056(3) 0.48174(15) 0.22816(11) 0.0313(4) Uani 1 1 d . . .
C13 C 1.1735(3) 0.41234(16) 0.20870(13) 0.0398(5) Uani 1 1 d . . .
H13 H 1.3117 0.4346 0.1823 0.048 Uiso 1 1 calc R . .
C14 C 1.1412(4) 0.30980(16) 0.22763(13) 0.0444(5) Uani 1 1 d . . .
H14 H 1.2565 0.2641 0.2134 0.053 Uiso 1 1 calc R . .
C15 C 1.0556(3) 0.59259(14) 0.21273(12) 0.0345(5) Uani 1 1 d . . .
H15A H 1.0709 0.6178 0.2620 0.041 Uiso 1 1 calc R . .
H15B H 1.2031 0.6011 0.1825 0.041 Uiso 1 1 calc R . .
C16 C 1.2872(5) 0.6043(3) -0.06035(16) 0.0741(9) Uani 1 1 d . . .
H16A H 1.4193 0.6261 -0.0372 0.111 Uiso 1 1 calc R . .
H16B H 1.3057 0.6216 -0.1157 0.111 Uiso 1 1 calc R . .
H16C H 1.2744 0.5327 -0.0482 0.111 Uiso 1 1 calc R . .
C17 C 1.0746(5) 0.6547(3) -0.02951(14) 0.0714(8) Uani 1 1 d . . .
H17A H 1.0845 0.7272 -0.0421 0.086 Uiso 1 1 calc R . .
H17B H 0.9395 0.6327 -0.0521 0.086 Uiso 1 1 calc R . .
C18 C 0.8826(4) 0.67048(17) 0.09257(13) 0.0423(5) Uani 1 1 d . . .
C19 C 0.6838(3) 0.70633(14) 0.19894(12) 0.0338(5) Uani 1 1 d . . .
C20 C 0.5852(4) 0.75195(16) 0.13112(13) 0.0408(5) Uani 1 1 d . . .
C21 C 0.3843(4) 0.81067(17) 0.13659(15) 0.0490(6) Uani 1 1 d . . .
H21 H 0.3186 0.8416 0.0921 0.059 Uiso 1 1 calc R . .
C22 C 0.2844(4) 0.82219(17) 0.20902(15) 0.0492(6) Uani 1 1 d . . .
H22 H 0.1497 0.8617 0.2136 0.059 Uiso 1 1 calc R . .
C23 C 0.3805(3) 0.77603(16) 0.27576(14) 0.0412(5) Uani 1 1 d . . .
H23 H 0.3067 0.7846 0.3240 0.049 Uiso 1 1 calc R . .
C24 C 0.5828(3) 0.71757(14) 0.27289(12) 0.0342(5) Uani 1 1 d . . .
C25 C 0.6844(3) 0.67386(14) 0.34742(12) 0.0339(5) Uani 1 1 d . . .
C26 C 0.1037(4) 0.58138(16) 0.53102(12) 0.0405(5) Uani 1 1 d . . .
H26A H 0.1071 0.6524 0.5368 0.049 Uiso 1 1 calc R . .
H26B H 0.2276 0.5469 0.5593 0.049 Uiso 1 1 calc R . .
C27 C 0.1256(4) 0.46023(16) 0.43619(13) 0.0405(5) Uani 1 1 d . . .
H27A H 0.2500 0.4218 0.4616 0.049 Uiso 1 1 calc R . .
H27B H 0.1452 0.4539 0.3811 0.049 Uiso 1 1 calc R . .
C28 C 0.2922(17) 0.0865(4) 0.0879(4) 0.232(4) Uani 1 1 d . . .
H28A H 0.3950 0.0311 0.0777 0.348 Uiso 1 1 calc R . .
H28B H 0.1756 0.0943 0.0509 0.348 Uiso 1 1 calc R . .
H28C H 0.2194 0.0734 0.1395 0.348 Uiso 1 1 calc R . .
H1 H 1.342(5) 0.022(2) 0.4477(18) 0.089(10) Uiso 1 1 d . . .
N1 N 1.3327(4) 0.08500(16) 0.43858(14) 0.0612(7) Uani 1 1 d . . .
N2 N 1.2270(4) 0.23827(14) 0.39560(12) 0.0536(5) Uani 1 1 d . . .
N3 N 0.8780(3) 0.65307(12) 0.17142(10) 0.0351(4) Uani 1 1 d . . .
N4 N 0.7146(3) 0.72803(14) 0.06475(11) 0.0480(5) Uani 1 1 d . . .
N5 N 0.1392(3) 0.56778(13) 0.44781(10) 0.0388(4) Uani 1 1 d . . .
H5A H 0.2790 0.5910 0.4289 0.047 Uiso 1 1 calc R . .
H5B H 0.0304 0.6040 0.4212 0.047 Uiso 1 1 calc R . .
O1 O 1.6147(4) 0.12185(13) 0.51846(13) 0.0881(7) Uani 1 1 d . . .
O2 O 1.4058(3) 0.23863(11) 0.44867(10) 0.0552(5) Uani 1 1 d . . .
O3 O 1.0563(3) 0.62766(12) 0.05332(9) 0.0523(4) Uani 1 1 d . . .
O4 O 0.8851(3) 0.69681(12) 0.35744(9) 0.0499(4) Uani 1 1 d . . .
O5 O 0.5648(3) 0.61611(13) 0.39524(10) 0.0571(5) Uani 1 1 d . . .
O6 O 0.4105(7) 0.1691(3) 0.08182(18) 0.1399(12) Uani 1 1 d . . .
H6A H 0.3688 0.2082 0.0450 0.210 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.211(3) . ?
C1 O2 1.333(3) . ?
C1 N1 1.343(3) . ?
C2 N2 1.283(3) . ?
C2 N1 1.362(3) . ?
C2 C3 1.470(3) . ?
C3 C4 1.401(3) . ?
C3 C8 1.404(3) . ?
C4 C5 1.368(4) . ?
C5 C6 1.361(4) . ?
C6 C7 1.381(3) . ?
C7 C8 1.387(3) . ?
C8 C9 1.495(3) . ?
C9 C14 1.379(3) . ?
C9 C10 1.382(3) . ?
C10 C11 1.380(3) . ?
C11 C12 1.384(3) . ?
C12 C13 1.374(3) . ?
C12 C15 1.508(3) . ?
C13 C14 1.386(3) . ?
C15 N3 1.460(2) . ?
C16 C17 1.479(4) . ?
C17 O3 1.437(3) . ?
C18 N4 1.302(3) . ?
C18 O3 1.326(3) . ?
C18 N3 1.359(3) . ?
C19 C24 1.395(3) . ?
C19 N3 1.396(3) . ?
C19 C20 1.408(3) . ?
C20 C21 1.384(3) . ?
C20 N4 1.393(3) . ?
C21 C22 1.370(3) . ?
C22 C23 1.389(3) . ?
C23 C24 1.386(3) . ?
C24 C25 1.505(3) . ?
C25 O4 1.241(2) . ?
C25 O5 1.247(2) . ?
C26 N5 1.479(3) . ?
C26 C27 1.500(3) 2_566 ?
C27 N5 1.485(3) . ?
C27 C26 1.500(3) 2_566 ?
C28 O6 1.309(6) . ?
N2 O2 1.436(2) . ?

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
_geom_angle_publ_flag
O1 C1 O2 122.6(2) . . ?
O1 C1 N1 130.8(2) . . ?
O2 C1 N1 106.5(2) . . ?
N2 C2 N1 110.7(2) . . ?
N2 C2 C3 126.23(19) . . ?
N1 C2 C3 123.03(19) . . ?
C4 C3 C8 119.2(2) . . ?
C4 C3 C2 117.73(19) . . ?
C8 C3 C2 123.07(18) . . ?
C5 C4 C3 121.1(2) . . ?
C6 C5 C4 119.7(2) . . ?
C5 C6 C7 120.5(2) . . ?
C6 C7 C8 121.4(2) . . ?
C7 C8 C3 118.1(2) . . ?
C7 C8 C9 118.2(2) . . ?
C3 C8 C9 123.73(19) . . ?
C14 C9 C10 118.81(18) . . ?
C14 C9 C8 121.21(19) . . ?
C10 C9 C8 119.94(18) . . ?
C11 C10 C9 120.53(18) . . ?
C10 C11 C12 120.96(19) . . ?
C13 C12 C11 118.10(18) . . ?
C13 C12 C15 119.67(17) . . ?
C11 C12 C15 122.14(18) . . ?
C12 C13 C14 121.36(19) . . ?
C9 C14 C13 120.1(2) . . ?
N3 C15 C12 114.04(15) . . ?
O3 C17 C16 107.3(2) . . ?
N4 C18 O3 127.8(2) . . ?
N4 C18 N3 115.4(2) . . ?
O3 C18 N3 116.72(19) . . ?
C24 C19 N3 134.02(18) . . ?
C24 C19 C20 121.72(19) . . ?
N3 C19 C20 104.24(18) . . ?
C21 C20 N4 128.9(2) . . ?
C21 C20 C19 120.2(2) . . ?
N4 C20 C19 110.97(19) . . ?
C22 C21 C20 118.4(2) . . ?
C21 C22 C23 121.2(2) . . ?
C24 C23 C22 122.2(2) . . ?
C23 C24 C19 116.27(19) . . ?
C23 C24 C25 119.51(19) . . ?
C19 C24 C25 124.18(18) . . ?
O4 C25 O5 123.52(19) . . ?
O4 C25 C24 117.68(16) . . ?
O5 C25 C24 118.80(17) . . ?
N5 C26 C27 109.77(16) . 2_566 ?
N5 C27 C26 110.63(18) . 2_566 ?
C1 N1 C2 108.8(2) . . ?
C2 N2 O2 105.22(17) . . ?
C18 N3 C19 105.93(17) . . ?
C18 N3 C15 123.00(18) . . ?
C19 N3 C15 131.03(17) . . ?
C18 N4 C20 103.42(18) . . ?
C26 N5 C27 111.41(16) . . ?
C1 O2 N2 108.66(17) . . ?
C18 O3 C17 116.54(18) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.048
