Growth "self-inhibition" of irbesartan desmotrope: surface intra-annular tautomer inter-conversion is the culprit.
Kang, Xiang; Zhang, Mingtao; Tang, Weiwei; Gong, Junbo; Chemical communications (Cambridge, England) 60 (2024) 3511–3514; doi:10.1039/d3cc06170a

data_7132771
_publ_section_title
;
 Growth "self-inhibition" of irbesartan desmotrope: surface intra-annular
 tautomer inter-conversion is the culprit.
;
_journal_issue                   26
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3511
_journal_page_last               3514
_journal_paper_doi               10.1039/d3cc06170a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C25 H28 N6 O, 0.562(C3 H8 O)'
_chemical_formula_sum            'C26.68 H32.49 N6 O1.56'
_chemical_formula_weight         462.29
_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
_audit_creation_date             2023-11-08
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-16 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   37.3204(19)
_cell_length_b                   37.3204(19)
_cell_length_c                   9.7227(6)
_cell_measurement_reflns_used    1386
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      50.6830
_cell_measurement_theta_min      5.3030
_cell_volume                     11727.6(11)
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 42.100a 64-bit (release 16-08-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.958
_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   -122.00 -76.00   0.50   12.00    --  -56.61-165.00 -10.00   92
  2  \w   -132.00 -70.00   0.50   12.00    --  -56.61 -19.00-134.00  124
  3  \w     48.00  73.00   0.50    3.00    --   -0.55  37.00 -90.00   50
  4  \w     14.00  40.00   0.50    3.00    --   -0.55  37.00 -90.00   52
  5  \w    -17.00   9.00   0.50   12.00    --   55.51 -19.00  90.00   52
  6  \w    -20.00  16.00   0.50   12.00    --   55.51 -19.00 120.00   72
  7  \w    -98.00 -65.00   0.50   12.00    --  -56.61 125.00-150.00   66
  8  \w    -91.00 -48.00   0.50   12.00    --  -56.61 125.00  30.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0470131000
_diffrn_orient_matrix_UB_12      0.0239014000
_diffrn_orient_matrix_UB_13      -0.0253938000
_diffrn_orient_matrix_UB_21      0.0010226000
_diffrn_orient_matrix_UB_22      0.0410195000
_diffrn_orient_matrix_UB_23      0.0308070000
_diffrn_orient_matrix_UB_31      0.0074714000
_diffrn_orient_matrix_UB_32      -0.0042925000
_diffrn_orient_matrix_UB_33      0.1534212000
_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  0.0374
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            6490
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        51.431
_diffrn_reflns_theta_max         51.431
_diffrn_reflns_theta_min         2.368
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.604
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_description       needle
_exptl_crystal_F_000             4448
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.00017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         2734
_refine_ls_number_restraints     46
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0615
_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^)+(0.0978P)^2^+25.0494P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1628
_refine_ls_wR_factor_ref         0.1719
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2197
_reflns_number_total             2734
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc06170a2.cif
_cod_data_source_block           exp_1053_1108_1
_cod_depositor_comments          'Adding full bibliography for 7132771.cif.'
_cod_original_cell_volume        11727.6(14)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               7132771
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C25 H28 N6 O'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.633(3)
 0.367(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 C17-C65 \\sim C17-C74
 with sigma of 0.02
 C37-C71 \\sim C66-C58
 with sigma of 0.02
 C65-C71 \\sim C74-C58
 with sigma of 0.04
 C65-C37 \\sim C74-C66
 with sigma of 0.02
 C17-C37 \\sim C17-C66
 with sigma of 0.04
4. Rigid bond restraints
 C17, C74, C66, C58
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
C17 \\sim C74 \\sim C66 \\sim C58: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
6. Rigid body (RIGU) restrains
 C65, C37, C71
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C74, C66, C58
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
7. Others
 Sof(H17C)=Sof(H17D)=Sof(C74)=Sof(H74A)=Sof(H74B)=Sof(C66)=Sof(H66A)=Sof(H66B)=
 Sof(C58)=Sof(H58A)=Sof(H58B)=Sof(H58C)=1-FVAR(1)
 Sof(H17A)=Sof(H17B)=Sof(C65)=Sof(H65A)=Sof(H65B)=Sof(C37)=Sof(H37A)=Sof(H37B)=
 Sof(C71)=Sof(H71A)=Sof(H71B)=Sof(H71C)=FVAR(1)
 Sof(O68)=Sof(H68)=Sof(C52)=Sof(H52A)=Sof(H52B)=Sof(H52C)=Sof(C16)=Sof(H16)=
 Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(2)
8.a Ternary CH refined with riding coordinates:
 C16(H16)
8.b Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B), C41(H41A,H41B), C84(H84A,H84B), C83(H83A,H83B), C80(H80A,
 H80B), C17(H17A,H17B), C17(H17C,H17D), C65(H65A,H65B), C37(H37A,H37B),
 C74(H74A,H74B), C66(H66A,H66B)
8.c Aromatic/amide H refined with riding coordinates:
 C59(H59), C49(H49), C34(H34), C20(H20), C22(H22), C5(H5), C11(H11), C19(H19)
8.d Idealised Me refined as rotating group:
 C71(H71A,H71B,H71C), C58(H58A,H58B,H58C), C52(H52A,H52B,H52C), C10(H10A,H10B,
 H10C)
8.e Idealised tetrahedral OH refined as rotating group:
 O68(H68)
;
_shelx_res_checksum              29507
_shelx_hkl_checksum              61967
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.473
_oxdiff_exptl_absorpt_empirical_full_min 0.721