A score and nine years of irbesartan
Ochsenbein, Philippe; Bonin, Michel; Fadaei-Tirani, Farzaneh; Lemée, Marie-Hélène; Kieffer, Jérôme; Görl, Daniel; El-Hajji, Mohamed; Schenk-Joß, Kurt; CrystEngComm 26 (2024) 4566–4578; doi:10.1039/D3CE01172K

data_7248995
_publ_section_title
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 A score and nine years of irbesartan
;
_journal_issue                   34
_journal_name_full               CrystEngComm
_journal_page_first              4566
_journal_page_last               4578
_journal_paper_doi               10.1039/D3CE01172K
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C25 H28 N6 O, 0.4[H2O]'
_chemical_formula_sum            'C25 H28 N6 O'
_chemical_formula_weight         428.52
_chemical_name_common            SR47436-A
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-04-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-04-27 deposited with the CCDC.	2024-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   37.4596(7)
_cell_length_b                   37.4596(7)
_cell_length_c                   9.8361(2)
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    293(1)
_cell_measurement_theta_max      57.3
_cell_measurement_theta_min      2.359
_cell_volume                     11953.1(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2016.5.0.1'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_detector_type            'APEX II'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX_DUO'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            37052
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        57.461
_diffrn_reflns_theta_max         57.461
_diffrn_reflns_theta_min         2.359
_diffrn_source                   'Incoatec microsource'
_exptl_absorpt_coefficient_mu    0.543
_exptl_absorpt_correction_T_max  0.7513
_exptl_absorpt_correction_T_min  0.6516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V2012/1 (Bruker AXS Inc.) was used for absorption correction.
wR2(int) was 0.1579 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.867.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_description       prism
_exptl_crystal_F_000             4104
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.016
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.000036(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         3621
_refine_ls_number_restraints     170
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0754P)^2^+5.7706P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1229
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3145
_reflns_number_total             3621
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce01172k2.cif
_cod_data_source_block           ibs_a_293k_zwitter
_cod_depositor_comments
'Adding full bibliography for 7248992--7248997.cif.'
_cod_original_cell_volume        11953.1(5)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               7248995
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.773
_exptl_absorpt_special_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2T2-C1 \\sim C3T2-C2T2 \\sim C3T2-C4T2 \\sim C2T1-C1 \\sim C2T1-C3T1 \\sim
C4T1-C3T1
 with sigma of 0.01
 C1-C3T2 \\sim C4T2-C2T2 \\sim C1-C3T1 \\sim C4T1-C2T1
 with sigma of 0.01
 C2T2-C1 \\sim C2GT-C1 \\sim C3GT-C2GT \\sim C4GT-C3GT
 with sigma of 0.01
 C1-C3GT \\sim C4GT-C2GT
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2GT \\sim C2T1 \\sim C2T2 \\sim C3GT \\sim C3T1 \\sim C3T2 \\sim C4GT
\\sim C4T1 \\sim C4T2: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
4. Others
 1*[Sof(H1AA)+Sof(H1AB)+Sof(C2T2)+Sof(H2TC)+Sof(H2TD)+Sof(C3T2)+Sof(H3TC)+
 Sof(H3TD)+Sof(C4T2)+Sof(H4TD)+Sof(H4TE)+Sof(H4TF)]+1*[Sof(H1BC)+Sof(H1BD)+
 Sof(C2T1)+Sof(H2TA)+Sof(H2TB)+Sof(C3T1)+Sof(H3TA)+Sof(H3TB)+Sof(C4T1)+
 Sof(H4TA)+Sof(H4TB)+Sof(H4TC)]+1*[Sof(H1CE)+Sof(H1CF)+Sof(C2GT)+Sof(H2GA)+
 Sof(H2GB)+Sof(C3GT)+Sof(H3GA)+Sof(H3GB)+Sof(C4GT)+Sof(H4GA)+Sof(H4GB)+
 Sof(H4GC)]=1 with esd of 0.001
 Sof(H1AA)=Sof(H1AB)=Sof(C2T2)=Sof(H2TC)=Sof(H2TD)=Sof(C3T2)=Sof(H3TC)=
 Sof(H3TD)=Sof(C4T2)=Sof(H4TD)=Sof(H4TE)=Sof(H4TF)=FVAR(1)
 Sof(H1BC)=Sof(H1BD)=Sof(C2T1)=Sof(H2TA)=Sof(H2TB)=Sof(C3T1)=Sof(H3TA)=
 Sof(H3TB)=Sof(C4T1)=Sof(H4TA)=Sof(H4TB)=Sof(H4TC)=FVAR(2)
 Sof(H1CE)=Sof(H1CF)=Sof(C2GT)=Sof(H2GA)=Sof(H2GB)=Sof(C3GT)=Sof(H3GA)=
 Sof(H3GB)=Sof(C4GT)=Sof(H4GA)=Sof(H4GB)=Sof(H4GC)=FVAR(3)
 Sof(H1N)=1-FVAR(4)
 Sof(H1)=FVAR(4)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1AA,H1AB), C1(H1BC,H1BD), C1(H1CE,H1CF), C1M(H1MA,H1MB), C2GT(H2GA,H2GB),
 C2T1(H2TA,H2TB), C2T2(H2TC,H2TD), C3GT(H3GA,H3GB), C3T1(H3TA,H3TB), C3T2(H3TC,
 H3TD), C6N(H6NA,H6NB), C7N(H7NA,H7NB), C8N(H8NA,H8NB), C9N(H9NA,H9NB)
5.b Me refined with riding coordinates:
 C4GT(H4GA,H4GB,H4GC), C4T1(H4TA,H4TB,H4TC), C4T2(H4TD,H4TE,H4TF)
5.c Aromatic/amide H refined with riding coordinates:
 C2B(H2B), C3B(H3B), C3P(H3P), C4P(H4P), C5B(H5B), C5P(H5P), C6B(H6B), C6P(H6P)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              39031
_shelx_fab_checksum              44321
_olex2_submission_special_instructions 'No special instructions were received'