Photoswitchable agonists for visible-light activation of the Wnt signaling pathway.
Ahmad, Shifa; Hashim, P. K.; Imajo, Masamichi; Cheruthu, Nusaiba Madappuram; Takahashi, Kiyonori; Tanaka, Shinya; Nakamura, Takayoshi; Tamaoki, Nobuyuki; Organic & biomolecular chemistry 23 (2025) 4240–4245; doi:10.1039/d4ob01827c

data_7160465
_publ_section_title
;
 Photoswitchable agonists for visible-light activation of the Wnt
 signaling pathway.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4240
_journal_page_last               4245
_journal_paper_doi               10.1039/d4ob01827c
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C18 H15 N5 O3, C4 H8 O2'
_chemical_formula_sum            'C22 H23 N5 O5'
_chemical_formula_weight         437.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-21
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-10-10 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                96.732(2)
_cell_angle_beta                 95.788(2)
_cell_angle_gamma                94.114(2)
_cell_formula_units_Z            2
_cell_length_a                   7.37273(19)
_cell_length_b                   9.0040(3)
_cell_length_c                   16.1224(4)
_cell_measurement_reflns_used    7760
_cell_measurement_temperature    222.9(3)
_cell_measurement_theta_max      72.0230
_cell_measurement_theta_min      4.9400
_cell_volume                     1053.68(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.99a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.99a (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 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      222.9(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.971
_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    -89.00  89.00   0.50    0.88    --    0.00  28.00 150.00  356
  2  \w    -89.00  89.00   0.50    0.88    --    0.00  46.00 -90.00  356
  3  \w    -84.00  94.00   0.50    3.51    --    5.00  18.00 -30.00  356
  4  \w   -184.00  -5.00   0.50    3.51    --  -94.70  55.00-126.04  358
  5  \w   -184.00  -5.00   0.50    3.51    --  -94.70  55.00-178.12  358
  6  \w   -184.00  -5.00   0.50    3.51    --  -94.70  42.00  19.51  358
  7  \w   -184.00  -5.00   0.50    3.51    --  -94.70   9.00-180.00  358
  8  \w   -184.00  -5.00   0.50    3.51    --  -94.70  55.00 110.09  358
  9  \w   -184.00  -5.00   0.50    3.51    --  -94.70  55.00 -31.17  358
 10  \w   -184.00  -5.00   0.50    3.51    --  -94.70  53.00-107.55  358
 11  \w   -184.00  -5.00   0.50    3.51    --  -94.70  55.00 161.16  358
 12  \w   -184.00  -5.00   0.50    3.51    --  -94.70  55.00  32.29  358
 13  \w   -184.00  -5.00   0.50    3.51    --  -94.70  55.00 -67.24  358
 14  \w    -89.00  89.00   0.50    0.88    --    0.00   9.00-150.00  356
 15  \w    -89.00  89.00   0.50    0.88    --    0.00  46.00   0.00  356
 16  \w   -184.00-101.00   0.50    3.51    --  -94.70  53.00  80.39  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0471902000
_diffrn_orient_matrix_UB_12      -0.0673993000
_diffrn_orient_matrix_UB_13      -0.0926584000
_diffrn_orient_matrix_UB_21      0.0660161000
_diffrn_orient_matrix_UB_22      0.1506271000
_diffrn_orient_matrix_UB_23      -0.0280053000
_diffrn_orient_matrix_UB_31      0.1945330000
_diffrn_orient_matrix_UB_32      -0.0516222000
_diffrn_orient_matrix_UB_33      -0.0014045000
_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  0.0292
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20019
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.637
_diffrn_reflns_theta_min         2.777
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.99a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0717P)^2^+0.2170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1328
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3216
_reflns_number_total             4049
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01827c2.cif
_cod_data_source_block           exp_798_auto
_cod_depositor_comments
'Adding full bibliography for 7160464--7160465.cif.'
_cod_database_code               7160465
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         C16H17N5O2
_chemical_oxdiff_usercomment     '223 K'
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.922
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C30(H30A,H30B)
2.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C2(H2), C13(H13), C8(H8), C19(H19), C9(H9), C21(H21), C20(H20)
2.c X=CH2 refined with riding coordinates:
 N26(H26A,H26B)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C32(H32A,H32B,H32C), C31(H31A,H31B,H31C)
;
_shelx_res_checksum              10054
_olex2_exptl_crystal_mounting_method Cryoloop
_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 1.066
_oxdiff_exptl_absorpt_empirical_full_min 0.930