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_7248994
_publ_section_title
;
 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'
_chemical_formula_sum            'C25 H28 N6 O'
_chemical_formula_weight         428.53
_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             2023-05-29
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-05-30 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                   37.2454(8)
_cell_length_b                   37.2454(8)
_cell_length_c                   9.65133(17)
_cell_measurement_reflns_used    7457
_cell_measurement_temperature    89.9(6)
_cell_measurement_theta_max      73.4430
_cell_measurement_theta_min      2.3540
_cell_volume                     11594.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/2 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      89.9(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -105.00 -36.00   0.50    2.00    --  -74.55 146.00  41.00  138
  2  \w     64.00 103.00   0.50    2.00    --   79.85-112.00-150.00   78
  3  \w     82.00 121.00   0.50    2.00    --   79.85 145.00-178.00   78
  4  \w     65.00  91.00   0.50    2.00    --   59.56  30.00-180.00   52
  5  \w     10.00  36.00   0.50    2.00    --   59.56 -30.00 -90.00   52
  6  \w     49.00  83.00   0.50    2.00    --   73.45 -95.00 -90.00   68
  7  \w   -122.00 -83.00   0.50    2.00    --  -74.55 -30.00-120.00   78
  8  \w   -112.00 -82.00   0.50    2.00    --  -75.95 -30.00 -90.00   60
  9  \w     82.00 118.00   0.50    2.00    --   79.85  30.00   0.00   72
 10  \w     35.00  66.00   0.50    2.00    --   79.85-111.00 -60.00   62
 11  \w     61.00  94.00   0.50    2.00    --   79.85-111.00 -90.00   66
 12  \w     38.00  71.00   0.50    2.00    --   79.85-111.00  30.00   66
 13  \w     56.00  81.00   0.50    2.00    --   79.85 -95.00  90.00   50
 14  \w     49.00  74.00   0.50    2.00    --   79.85 -95.00 -30.00   50
 15  \w     90.00 127.00   0.50    2.00    --   79.85  30.00-150.00   74
 16  \w     72.00 115.00   0.50    2.00    --   79.85  15.00  30.00   86
 17  \w     70.00 111.00   0.50    2.00    --   79.85  15.00 120.00   82
 18  \w     86.00 111.00   0.50    2.00    --   79.85  30.00 -90.00   50
 19  \w     36.00  69.00   0.50    2.00    --   79.85-111.00  60.00   66
 20  \w     78.00 103.00   0.50    2.00    --   79.85-111.00-120.00   50
 21  \w     63.00  96.00   0.50    2.00    --   79.85 156.00 154.00   66
 22  \w     46.00  71.00   0.50    2.00    --   79.85 -95.00 -90.00   50
 23  \w     45.00  70.00   0.50    2.00    --   79.85 -95.00 150.00   50
 24  \w     37.00 103.00   0.50    2.00    --   79.85-111.00 -30.00  132
 25  \w     84.00 114.00   0.50    2.00    --   79.85-136.00 -35.00   60
 26  \w     79.00 104.00   0.50    2.00    --   79.85 136.00  29.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0340493667
_diffrn_orient_matrix_UB_12      -0.0119892667
_diffrn_orient_matrix_UB_13      -0.0004634667
_diffrn_orient_matrix_UB_21      -0.0328340000
_diffrn_orient_matrix_UB_22      -0.0454059000
_diffrn_orient_matrix_UB_23      0.0301780000
_diffrn_orient_matrix_UB_31      -0.0064033333
_diffrn_orient_matrix_UB_32      -0.0086707667
_diffrn_orient_matrix_UB_33      -0.1567802667
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            30151
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.719
_diffrn_reflns_theta_min         2.373
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.619
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on Gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics
as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_description       needle
_exptl_crystal_F_000             4104
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.000047(8)
_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   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         5233
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0365P)^2^+12.5545P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4121
_reflns_number_total             5233
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce01172k2.cif
_cod_data_source_block           ibs-a-temp_06_90_00
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Gaussian' was
changed to 'gaussian' 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 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7248992--7248997.cif.
;
_cod_original_cell_volume        11594.8(5)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               7248994
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C25 H28 O N6'
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.799
_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) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2T1-C1 = C3T1-C2T1 = C4T1-C3T1 = C2T2-C1 = C3T2-C2T2 = C4T2-C3T2
 1.54 with sigma of 0.02
 C1-C3T2 = C2T2-C4T2
 2.54 with sigma of 0.02
 C1-C3T1 = C2T1-C4T1
 2.54 with sigma of 0.02
 C4T2-C3T2
 1.54 with sigma of 0.01
 C4T1-C3T1
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2T1 \\sim C2T2 \\sim C3T1 \\sim C3T2 \\sim C4T1 \\sim C4T2: within 2A
with sigma of 0.005 and sigma for terminal atoms of 0.01 within 2A
4. Others
 Sof(H1BC)=Sof(H1BD)=Sof(C2T2)=Sof(H2TC)=Sof(H2TD)=Sof(C3T2)=Sof(H3TC)=
 Sof(H3TD)=Sof(C4T2)=Sof(H4TD)=Sof(H4TE)=Sof(H4TF)=1-FVAR(1)
 Sof(H1AA)=Sof(H1AB)=Sof(C2T1)=Sof(H2TA)=Sof(H2TB)=Sof(C3T1)=Sof(H3TA)=
 Sof(H3TB)=Sof(C4T1)=Sof(H4TA)=Sof(H4TB)=Sof(H4TC)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1AA,H1AB), C1(H1BC,H1BD), C1M(H1MA,H1MB), C2T1(H2TA,H2TB), C2T2(H2TC,
 H2TD), C3T1(H3TA,H3TB), C3T2(H3TC,H3TD), C6N(H6NA,H6NB), C7N(H7NA,H7NB),
 C8N(H8NA,H8NB), C9N(H9NA,H9NB)
5.b Aromatic/amide H refined with riding coordinates:
 C2B(H2B), C3B(H3B), C3P(H3P), C4P(H4P), C5B(H5B), C5P(H5P), C6B(H6B), C6P(H6P)
5.c Idealised Me refined as rotating group:
 C4T1(H4TA,H4TB,H4TC), C4T2(H4TD,H4TE,H4TF)
;
_shelx_res_checksum              84369
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.375
_oxdiff_exptl_absorpt_empirical_full_min 0.522