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_7160464
_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_absolute_configuration unk
_chemical_formula_moiety         'C17 H15 N5 O'
_chemical_formula_sum            'C17 H15 N5 O'
_chemical_formula_weight         305.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-10-10
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_audit_update_record
;
2024-10-10 deposited with the CCDC.	2025-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.788(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2189(3)
_cell_length_b                   25.5663(11)
_cell_length_c                   9.9465(6)
_cell_measurement_reflns_used    5697
_cell_measurement_temperature    272.7(8)
_cell_measurement_theta_max      70.3150
_cell_measurement_theta_min      3.4220
_cell_volume                     1834.84(16)
_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 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      272.7(8)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_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    -86.00 -59.00   0.50    3.19    --    0.00  37.00  30.00   54
  2  \w    -30.00  -3.00   0.50    3.19    --    0.00  37.00  30.00   54
  3  \w     31.00  57.00   0.50    3.19    --    0.00  37.00  30.00   52
  4  \w    -22.00  94.00   0.50   12.78    --    5.00  18.00  30.00  232
  5  \w   -153.00 -87.00   0.50   12.78    --  -94.70  28.00  60.00  132
  6  \w   -183.00-157.00   0.50   12.78    --  -94.70  46.00  90.00   52
  7  \w   -183.00 -30.00   0.50   12.78    --  -94.70  18.00-120.00  306
  8  \w   -165.00 -96.00   0.50   12.78    --  -94.70  18.00  30.00  138
  9  \w   -179.00 -63.00   0.50   12.78    --  -94.70  46.00 120.00  232
 10  \w    -71.00  -5.00   0.50   12.78    --  -94.70  46.00  90.00  132
 11  \w   -127.00 -80.00   0.50   12.78    --  -94.70  46.00  90.00   94
 12  \w   -112.00 -83.00   0.50   12.78    --  -94.70  53.00  52.34   58
 13  \w   -167.00-137.00   0.50   12.78    --  -94.70  53.00  52.34   60
 14  \w    -47.00  -6.00   0.50    3.19    --    0.00  37.00-180.00   82
 15  \w    -62.00 -35.00   0.50    3.19    --    0.00  46.00  60.00   54
 16  \w     57.00  89.00   0.50    3.19    --    0.00  37.00-180.00   64
 17  \w      4.00  51.00   0.50    3.19    --    0.00  37.00-180.00   94
 18  \w   -138.00 -93.00   0.50   12.78    --  -94.70  46.00   0.00   90
 19  \w    -49.00  -6.00   0.50   12.78    --  -94.70  46.00   0.00   86
 20  \w   -168.00-102.00   0.50   12.78    --  -94.70  55.00 160.04  132
 21  \w    -61.00  -5.00   0.50   12.78    --  -94.70  50.00 112.55  112
 22  \w    -96.00 -53.00   0.50   12.78    --  -94.70  54.00  70.88   86
 23  \w    -30.00  -5.00   0.50   12.78    --  -94.70  52.00 178.75   50
 24  \w    -60.00  -5.00   0.50   12.78    --  -94.70  49.00 133.05  110
 25  \w    -74.00  -5.00   0.50   12.78    --  -94.70  54.00  25.59  138
 26  \w    -36.00 -11.00   0.50   12.78    --  -94.70  55.00 136.70   50
 27  \w    -52.00 -11.00   0.50   12.78    --  -94.70  46.00 -30.00   82
 28  \w    -35.00  -6.00   0.50   12.78    --  -94.70  52.00 169.41   58
 29  \w   -150.00-124.00   0.50   12.78    --  -94.70  52.00 178.75   52
 30  \w    -56.00  -6.00   0.50   12.78    --  -94.70  55.00 160.04  100
 31  \w    -54.00  -6.00   0.50   12.78    --  -94.70  46.00-180.00   96
 32  \w    -75.00 -40.00   0.50   12.78    --  -94.70  55.00  82.77   70
 33  \w   -166.00-122.00   0.50   12.78    --  -94.70  55.00  82.77   88
;
_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      0.0792253000
_diffrn_orient_matrix_UB_12      -0.0559611000
_diffrn_orient_matrix_UB_13      0.0032580000
_diffrn_orient_matrix_UB_21      -0.0093313000
_diffrn_orient_matrix_UB_22      -0.0016773000
_diffrn_orient_matrix_UB_23      -0.1548508000
_diffrn_orient_matrix_UB_31      0.1981187000
_diffrn_orient_matrix_UB_32      0.0222659000
_diffrn_orient_matrix_UB_33      -0.0035369000
_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  0.0498
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21086
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.612
_diffrn_reflns_theta_min         3.457
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.590
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34970
_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    1.105
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1917 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         7079
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0909P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1484
_reflns_Friedel_coverage         0.920
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.955
_reflns_number_gt                5005
_reflns_number_total             7079
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01827c2.cif
_cod_data_source_block           exp_793_auto_sq
_cod_depositor_comments
'Adding full bibliography for 7160464--7160465.cif.'
_cod_original_cell_volume        1834.82(16)
_cod_database_code               7160464
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C17H15N5O
_chemical_oxdiff_usercomment     223k
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C6(H6), C44(H44), C35(H35), C45(H45), C11(H11), C10(H10), C31(H31),
 C8(H8), C33(H33), C18(H18), C25(H25), C41(H41), C32(H32), C43(H43), C42(H42),
 C22(H22), C20(H20), C21(H21), C19(H19)
2.b X=CH2 refined with riding coordinates:
 N23(H23A,H23B), N46(H46A,H46B)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C37(H37A,H37B,H37C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              73853
_shelx_fab_checksum              68042
_platon_squeeze_void_probe_radius 1.20
_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 1.891
_oxdiff_exptl_absorpt_empirical_full_min 0.407