#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:52:38 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301791 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/73/2007383.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2007383
loop_
_publ_author_name
'Böcskei, Zsolt'
'Simon, Kálmán'
'Rao, Renée'
'Caron, Antoine'
'Rodger, Charles A.'
'Bauer, Michel'
_publ_section_title
;
 Irbesartan Crystal Form B
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              808
_journal_page_last               810
_journal_paper_doi               10.1107/S0108270197019884
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C25 H28 N6 O'
_chemical_formula_sum            'C25 H28 N6 O'
_chemical_formula_weight         428.53
_chemical_name_common            Irbesartan
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.75(4)
_cell_angle_beta                 105.24(4)
_cell_angle_gamma                112.92(3)
_cell_formula_units_Z            2
_cell_length_a                   11.170(5)
_cell_length_b                   12.181(4)
_cell_length_c                   9.366(4)
_cell_measurement_reflns_used    9
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      51.6
_cell_measurement_theta_min      40.2
_cell_volume                     1122.9(9)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1988)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1985, 1992)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Rigaku AFC-6S'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.090
_diffrn_reflns_av_sigmaI/netI    0.025
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4509
_diffrn_reflns_theta_max         75.16
_diffrn_reflns_theta_min         3.97
_diffrn_standards_decay_%        1.09
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  0.773
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_type   '\y scan (North et al., 1968)'
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    none
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.8
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.387
_refine_ls_extinction_coef       0.0105(12)
_refine_ls_extinction_method     SHELXL93
_refine_ls_goodness_of_fit_all   1.029
_refine_ls_goodness_of_fit_obs   1.060
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4305
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.162
_refine_ls_restrained_S_obs      1.060
_refine_ls_R_factor_all          0.077
_refine_ls_R_factor_obs          .062
_refine_ls_shift/esd_max         0.002
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0867P)²+0.8048P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.204
_refine_ls_wR_factor_obs         .170
_reflns_number_observed          3624
_reflns_number_total             4312
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            sx1039.cif
_cod_data_source_block           sr47436
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0867P)^2^+0.8048P] where P = (Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0867P)^2^+0.8048P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1122.9(8)
_cod_database_code               2007383
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
N1 .4011(2) .6618(2) -.2437(2) .0394(4) Uani d . 1 . N
C2 .3178(2) .5681(2) -.3565(3) .0458(5) Uani d . 1 . C
N3 .3388(2) .5865(2) -.4839(2) .0486(5) Uani d . 1 . N
C4 .4490(2) .7064(2) -.4659(2) .0434(5) Uani d . 1 . C
C5 .4858(2) .7514(2) -.3021(3) .0455(5) Uani d . 1 . C
C6 .4048(3) .7913(3) -.5672(4) .0715(8) Uani d . 1 . C
H6A .3280(3) .7456(3) -.6526(4) .094(3) Uiso calc R 1 . H
H6B .3797(3) .8428(3) -.5124(4) .094(3) Uiso calc R 1 . H
C7 .5265(4) .8643(4) -.6164(5) .0943(12) Uani d . 1 . C
H7A .4998(4) .8945(4) -.7094(5) .094(3) Uiso calc R 1 . H
H7B .5899(4) .9317(4) -.5412(5) .094(3) Uiso calc R 1 . H
C8 .5870(4) .7782(4) -.6359(4) .0921(12) Uani d . 1 . C
H8A .6820(4) .8207(4) -.6310(4) .094(3) Uiso calc R 1 . H
H8B .5391(4) .7278(4) -.7314(4) .094(3) Uiso calc R 1 . H
C9 .5723(3) .7037(3) -.5094(3) .0546(6) Uani d . 1 . C
H9A .6538(3) .7374(3) -.4253(3) .094(3) Uiso calc R 1 . H
H9B .5565(3) .6218(3) -.5409(3) .094(3) Uiso calc R 1 . H
C10 .4095(2) .6653(2) -.0844(2) .0424(5) Uani d . 1 . C
H10A .5018(2) .7166(2) -.0267(2) .094(3) Uiso calc R 1 . H
H10B .3899(2) .5850(2) -.0569(2) .094(3) Uiso calc R 1 . H
C11 .3137(2) .7108(2) -.0433(2) .0377(5) Uani d . 1 . C
C12 .2023(2) .6349(2) -.0013(2) .0396(5) Uani d . 1 . C
H12 .1853(2) .5538(2) -.0007(2) .058(3) Uiso calc R 1 . H
C13 .1164(2) .6771(2) .0397(2) .0399(5) Uani d . 1 . C
H13 .0430(2) .6242(2) .0680(2) .058(3) Uiso calc R 1 . H
C14 .1380(2) .7978(2) .0395(2) .0379(5) Uani d . 1 . C
C15 .2507(2) .8742(2) -.0017(3) .0451(5) Uani d . 1 . C
H15 .2684(2) .9554(2) -.0017(3) .058(3) Uiso calc R 1 . H
C16 .3366(2) .8315(2) -.0426(3) .0445(5) Uani d . 1 . C
H16 .4106(2) .8843(2) -.0700(3) .058(3) Uiso calc R 1 . H
C17 .0528(2) .8476(2) .0922(2) .0394(5) Uani d . 1 . C
C18 -.0898(2) .7975(2) .0472(2) .0372(5) Uani d . 1 . C
C19 -.1577(2) .8496(2) .1115(3) .0471(6) Uani d . 1 . C
H19 -.2522(2) .8162(2) .0819(3) .058(3) Uiso calc R 1 . H
C20 -.0880(3) .9495(2) .2178(3) .0555(6) Uani d . 1 . C
H20 -.1352(3) .9820(2) .2608(3) .058(3) Uiso calc R 1 . H
C21 .0508(3) 1.0005(2) .2597(3) .0575(7) Uani d . 1 . C
H21 .0984(3) 1.0692(2) .3293(3) .058(3) Uiso calc R 1 . H
C22 .1204(2) .9499(2) .1985(3) .0511(6) Uani d . 1 . C
H22 .2149(2) .9849(2) .2288(3) .058(3) Uiso calc R 1 . H
C23 -.1775(2) .6935(2) -.0687(2) .0362(5) Uani d . 1 . C
N24 -.1482(2) .6593(2) -.1859(2) .0455(5) Uani d . 1 . N
N25 -.2626(2) .5661(2) -.2542(2) .0442(5) Uani d . 1 . N
H25 -.2735(2) .5248(2) -.3353(2) .058(3) Uiso calc R 1 . H
N26 -.3571(2) .5424(2) -.1880(2) .0492(5) Uani d . 1 . N
N27 -.3052(2) .6222(2) -.0683(2) .0470(5) Uani d . 1 . N
C28 .2125(4) .4598(3) -.3250(4) .0860(12) Uani d D 1 . C
H28C .1430(4) .4844(3) -.3114(4) .094(3) Uiso calc PR .341(12) 2 H
H28D .2546(4) .4427(3) -.2283(4) .094(3) Uiso calc PR .341(12) 2 H
H28A .1682(4) .4842(3) -.2623(4) .094(3) Uiso calc PR .659(12) 1 H
H28B .2554(4) .4112(3) -.2707(4) .094(3) Uiso calc PR .659(12) 1 H
C29A .1045(5) .3834(4) -.4700(5) .0458(13) Uani d PD .659(12) 1 C
H29A .0746(5) .4352(4) -.5344(5) .094(3) Uiso calc PR .659(12) 1 H
H29B .1442(5) .3444(4) -.5229(5) .094(3) Uiso calc PR .659(12) 1 H
C29B .1383(11) .3414(11) -.4230(14) .074(3) Uani d PD .341(12) 2 C
H29C .1407(11) .2761(11) -.3658(14) .094(3) Uiso calc PR .341(12) 2 H
H29D .1783(11) .3402(11) -.5029(14) .094(3) Uiso calc PR .341(12) 2 H
C30A -.0170(5) .2885(4) -.4332(4) .062(2) Uani d PD .659(12) 1 C
H30A .0119(5) .2387(4) -.3644(4) .094(3) Uiso calc PR .659(12) 1 H
H30B -.0630(5) .3261(4) -.3885(4) .094(3) Uiso calc PR .659(12) 1 H
C30B -.0050(10) .3305(9) -.4845(18) .138(9) Uani d PD .341(12) 2 C
H30C -.0026(10) .3963(9) -.5425(18) .094(3) Uiso calc PR .341(12) 2 H
H30D -.0369(10) .3418(9) -.4010(18) .094(3) Uiso calc PR .341(12) 2 H
C31 -.1104(4) .2136(4) -.5823(4) .1042(15) Uani d D 1 . C
H31A -.1895(4) .1518(4) -.5667(4) .21(2) Uiso calc PR .659(12) 1 H
H31B -.0630(4) .1776(4) -.6250(4) .21(2) Uiso calc PR .659(12) 1 H
H31C -.1375(4) .2645(4) -.6489(4) .21(2) Uiso calc PR .659(12) 1 H
H31D -.1971(4) .2184(4) -.6141(4) .21(2) Uiso calc PR .341(12) 2 H
H31E -.1174(4) .1473(4) -.5260(4) .21(2) Uiso calc PR .341(12) 2 H
H31F -.0829(4) .2020(4) -.6681(4) .21(2) Uiso calc PR .341(12) 2 H
O32 .5715(2) .8457(2) -.2336(2) .0730(6) Uani d . 1 . O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C5 N1 C2 108.4(2) ?
C5 N1 C10 123.7(2) ?
C2 N1 C10 127.7(2) ?
N3 C2 N1 114.4(2) ?
N3 C2 C28 125.7(2) ?
N1 C2 C28 119.9(2) ?
C2 N3 C4 107.7(2) ?
N3 C4 C5 103.6(2) ?
N3 C4 C6 112.6(2) ?
C5 C4 C6 111.7(2) ?
N3 C4 C9 113.0(2) ?
C5 C4 C9 111.8(2) ?
C6 C4 C9 104.3(2) ?
O32 C5 N1 125.5(2) ?
O32 C5 C4 128.6(2) ?
N1 C5 C4 106.0(2) ?
C7 C6 C4 105.2(3) ?
C8 C7 C6 103.9(3) ?
C7 C8 C9 105.3(3) ?
C8 C9 C4 106.0(2) ?
N1 C10 C11 113.8(2) ?
C12 C11 C16 117.9(2) ?
C12 C11 C10 121.4(2) ?
C16 C11 C10 120.7(2) ?
C13 C12 C11 121.4(2) ?
C12 C13 C14 121.0(2) ?
C13 C14 C15 117.4(2) ?
C13 C14 C17 122.3(2) ?
C15 C14 C17 120.1(2) ?
C16 C15 C14 121.3(2) ?
C15 C16 C11 120.9(2) ?
C22 C17 C18 117.8(2) ?
C22 C17 C14 117.1(2) ?
C18 C17 C14 125.0(2) ?
C19 C18 C17 119.2(2) ?
C19 C18 C23 115.6(2) ?
C17 C18 C23 125.2(2) ?
C20 C19 C18 121.5(2) ?
C21 C20 C19 119.5(2) ?
C20 C21 C22 120.0(2) ?
C21 C22 C17 121.9(2) ?
N24 C23 N27 111.4(2) ?
N24 C23 C18 127.2(2) ?
N27 C23 C18 121.4(2) ?
N25 N24 C23 101.8(2) ?
N26 N25 N24 114.2(2) y
N25 N26 N27 106.3(2) ?
N26 N27 C23 106.3(2) ?
C2 C28 C29B 125.6(5) ?
C2 C28 C29A 111.8(3) ?
C30A C29A C28 110.2(3) ?
C28 C29B C30B 104.9(8) ?
C31 C30A C29A 105.3(3) ?
C29B C30B C31 117.9(8) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C5 . 1.367(3) y
N1 C2 . 1.382(3) y
N1 C10 . 1.469(3) y
C2 N3 . 1.282(3) y
C2 C28 . 1.482(4) y
N3 C4 . 1.470(3) y
C4 C5 . 1.514(3) y
C4 C6 . 1.546(4) y
C4 C9 . 1.548(3) y
C5 O32 . 1.203(3) y
C6 C7 . 1.499(5) y
C7 C8 . 1.485(6) y
C8 C9 . 1.507(4) y
C10 C11 . 1.508(3) y
C11 C12 . 1.389(3) ?
C11 C16 . 1.391(3) ?
C12 C13 . 1.380(3) ?
C13 C14 . 1.395(3) ?
C14 C15 . 1.397(3) ?
C14 C17 . 1.486(3) ?
C15 C16 . 1.382(3) ?
C17 C22 . 1.397(3) ?
C17 C18 . 1.403(3) ?
C18 C19 . 1.395(3) ?
C18 C23 . 1.477(3) y
C19 C20 . 1.379(4) ?
C20 C21 . 1.367(4) ?
C21 C22 . 1.382(4) ?
C23 N24 . 1.330(3) y
C23 N27 . 1.352(3) y
N24 N25 . 1.324(3) y
N25 N26 . 1.302(3) y
N26 N27 . 1.315(3) y
C28 C29B . 1.498(10) ?
C28 C29A . 1.548(5) ?
C29A C30A . 1.527(6) ?
C29B C30B . 1.503(15) ?
C30A C31 . 1.527(2) ?
C30B C31 . 1.531(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_publ_flag
C5 N1 C2 N3 0.1(3) y
C10 N1 C2 N3 -175.2(2) ?
C5 N1 C2 C28 -178.2(3) ?
C10 N1 C2 C28 6.5(4) ?
N1 C2 N3 C4 -0.2(3) y
C28 C2 N3 C4 178.0(3) ?
C2 N3 C4 C5 0.2(3) y
C2 N3 C4 C6 -120.7(2) y
C2 N3 C4 C9 121.4(2) y
C2 N1 C5 O32 -179.7(3) ?
C10 N1 C5 O32 -4.2(4) ?
C2 N1 C5 C4 0.0(2) y
C10 N1 C5 C4 175.5(2) ?
N3 C4 C5 O32 179.6(3) ?
C6 C4 C5 O32 -58.9(4) y
C9 C4 C5 O32 57.6(4) y
N3 C4 C5 N1 -0.1(2) y
C6 C4 C5 N1 121.3(2) y
C9 C4 C5 N1 -122.1(2) y
N3 C4 C6 C7 -143.0(3) y
C5 C4 C6 C7 100.9(3) y
C9 C4 C6 C7 -20.1(3) y
C4 C6 C7 C8 36.5(4) y
C6 C7 C8 C9 -39.0(4) y
C7 C8 C9 C4 26.0(4) y
N3 C4 C9 C8 119.2(3) y
C5 C4 C9 C8 -124.3(3) y
C6 C4 C9 C8 -3.4(3) y
C5 N1 C10 C11 95.7(3) y
C2 N1 C10 C11 -89.7(3) ?
N1 C10 C11 C12 110.3(2) y
N1 C10 C11 C16 -71.5(3) ?
C16 C11 C12 C13 0.2(3) ?
C10 C11 C12 C13 178.5(2) ?
C11 C12 C13 C14 0.4(3) ?
C12 C13 C14 C15 -0.9(3) ?
C12 C13 C14 C17 -176.0(2) ?
C13 C14 C15 C16 0.8(3) ?
C17 C14 C15 C16 176.0(2) ?
C14 C15 C16 C11 -0.3(4) ?
C12 C11 C16 C15 -0.2(3) ?
C10 C11 C16 C15 -178.5(2) ?
C13 C14 C17 C22 128.2(2) y
C15 C14 C17 C22 -46.8(3) ?
C13 C14 C17 C18 -49.6(3) y
C15 C14 C17 C18 135.4(2) ?
C22 C17 C18 C19 -1.2(3) ?
C14 C17 C18 C19 176.6(2) ?
C22 C17 C18 C23 176.8(2) ?
C14 C17 C18 C23 -5.4(3) ?
C17 C18 C19 C20 0.3(4) ?
C23 C18 C19 C20 -178.0(2) ?
C18 C19 C20 C21 1.3(4) ?
C19 C20 C21 C22 -1.8(4) ?
C20 C21 C22 C17 0.8(4) ?
C18 C17 C22 C21 0.7(4) ?
C14 C17 C22 C21 -177.3(2) ?
C19 C18 C23 N24 149.8(2) ?
C17 C18 C23 N24 -28.3(3) y
C19 C18 C23 N27 -27.6(3) ?
C17 C18 C23 N27 154.3(2) ?
N27 C23 N24 N25 0.1(2) ?
C18 C23 N24 N25 -177.5(2) ?
C23 N24 N25 N26 0.2(3) ?
N24 N25 N26 N27 -0.4(3) ?
N25 N26 N27 C23 0.5(2) ?
N24 C23 N27 N26 -0.4(3) ?
C18 C23 N27 N26 177.4(2) ?
N3 C2 C28 C29B 17.3(9) ?
N1 C2 C28 C29B -164.6(8) ?
N3 C2 C28 C29A -14.8(5) ?
N1 C2 C28 C29A 163.3(3) ?
C2 C28 C29A C30A -168.0(5) ?
C29B C28 C29A C30A 68.7(10) ?
C2 C28 C29B C30B -110.3(11) ?
C29A C28 C29B C30B -37.8(11) ?
C28 C29A C30A C31 -175.8(4) ?
C28 C29B C30B C31 -176.0(10) ?
C29A C30A C31 C30B -31.2(11) ?
C29B C30B C31 C30A 73.5(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 3749
