Photochromic Indolyl Fulgimides as Chromo-pharmacophores Targeting Sirtuins.
Simeth, Nadja A.; Altmann, Lisa-Marie; Wössner, Nathalie; Bauer, Elisabeth; Jung, Manfred; König, Burkhard; The Journal of organic chemistry 83 (2018) 7919–7927; doi:10.1021/acs.joc.8b00795

data_4035603
_publ_section_title
;
 Photochromic Indolyl Fulgimides as Chromo-pharmacophores Targeting
 Sirtuins.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7919
_journal_page_last               7927
_journal_paper_doi               10.1021/acs.joc.8b00795
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C24 H22 N2 O3'
_chemical_formula_sum            'C24 H22 N2 O3'
_chemical_formula_weight         386.43
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-08
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                104.087(3)
_cell_angle_beta                 108.553(3)
_cell_angle_gamma                93.234(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6373(3)
_cell_length_b                   9.6529(3)
_cell_length_c                   11.2938(4)
_cell_measurement_reflns_used    10881
_cell_measurement_temperature    293.48(10)
_cell_measurement_theta_max      73.5170
_cell_measurement_theta_min      4.7450
_cell_volume                     955.79(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.48(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_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   -116.00 -17.00   1.00    2.00    --  -41.48 -37.00  90.00   99
  2  \w    -98.00  -2.00   1.00    2.00    --  -41.48 125.00-150.00   96
  3  \w      2.00  98.00   1.00    2.00    --   41.48-125.00   0.00   96
  4  \w     13.00 115.00   1.00    2.00    --   41.48  57.00-150.00  102
  5  \w    -31.00  70.00   1.00    2.00    --   41.48 -57.00  60.00  101
  6  \w     13.00 117.00   1.00    2.00    --   44.00  69.00-109.19  104
  7  \w     14.00  46.00   1.00    2.00    --   48.00  81.00 -21.78   32
  8  \w     19.00  47.00   1.00    2.00    --   52.00  79.00 152.61   28
  9  \w     18.00  45.00   1.00    2.00    --   52.00  82.00-164.79   27
 10  \w     19.00  47.00   1.00    2.00    --   52.00  79.00  55.38   28
 11  \w     18.00  46.00   1.00    2.00    --   52.00  81.00 -94.46   28
 12  \w     27.00 136.00   1.00    2.00    --   60.00  77.00 110.23  109
 13  \w     28.00 135.00   1.00    2.00    --   60.00  75.00  -3.78  107
 14  \w     31.00 140.00   1.00    2.00    --   64.00  77.00 -33.02  109
 15  \w     32.00 139.00   1.00    2.00    --   64.00  75.00-132.16  107
 16  \w     32.00 140.00   1.00    2.00    --   64.00  76.00  51.83  108
 17  \w     31.00 140.00   1.00    2.00    --   64.00  77.00-161.36  109
 18  \w     35.00 144.00   1.00    2.00    --   68.00  77.00 -80.58  109
 19  \w     36.00 144.00   1.00    2.00    --   68.00  76.00 148.88  108
 20  \w     24.00 109.00   1.00    8.00    --  106.46 -94.00-150.00   85
 21  \w     33.00  77.00   1.00    8.00    --  106.46 -45.00 -60.00   44
 22  \w     77.00 158.00   1.00    8.00    --  106.46  61.00-150.00   81
 23  \w     77.00 158.00   1.00    8.00    --  106.46  61.00  90.00   81
 24  \w     74.00 158.00   1.00    8.00    --  106.46  77.00   0.00   84
 25  \w     77.00 158.00   1.00    8.00    --  106.46  61.00 -30.00   81
 26  \w     24.00 109.00   1.00    8.00    --  106.46 -94.00  90.00   85
 27  \w     74.00 158.00   1.00    8.00    --  106.46  77.00  60.00   84
 28  \w     33.00  77.00   1.00    8.00    --  106.46 -45.00  60.00   44
 29  \w     33.00 121.00   1.00    8.00    --  106.46-125.00   0.00   88
 30  \w     77.00 158.00   1.00    8.00    --  106.46  61.00 -60.00   81
 31  \w     74.00 158.00   1.00    8.00    --  106.46  77.00-120.00   84
 32  \w     74.00 158.00   1.00    8.00    --  106.46  77.00 -30.00   84
 33  \w     74.00 158.00   1.00    8.00    --  106.46  77.00 150.00   84
 34  \w     30.00 139.00   1.00    8.00    --  106.46 -77.00-120.00  109
 35  \w     74.00 158.00   1.00    8.00    --  106.46  77.00 120.00   84
 36  \w     77.00 158.00   1.00    8.00    --  106.46  61.00  30.00   81
 37  \w     77.00 158.00   1.00    8.00    --  106.46  61.00-120.00   81
 38  \w     77.00 107.00   1.00    8.00    --  106.46  61.00 120.00   30
 39  \w     35.00  61.00   1.00    8.00    --  106.46 -45.00   0.00   26
 40  \w     33.00 115.00   1.00    8.00    --  106.46-125.00-150.00   82
 41  \w     80.00 132.00   1.00    8.00    --  106.46  61.00   0.00   52
 42  \w     79.00 126.00   1.00    8.00    --  106.46  77.00  30.00   47
 43  \w    129.00 155.00   1.00    8.00    --  106.46  77.00  30.00   26
 44  \w     42.00  68.00   1.00    8.00    --  106.46 -45.00  90.00   26
 45  \w    116.00 157.00   1.00    8.00    --  106.46  61.00-180.00   41
 46  \w     77.00 104.00   1.00    8.00    --  106.46  61.00-180.00   27
 47  \w     33.00  63.00   1.00    8.00    --  106.46 -45.00-120.00   30
 48  \w     76.00 143.00   1.00    8.00    --  106.46  77.00 -90.00   67
 49  \w     31.00  97.00   1.00    8.00    --  106.46 -94.00  30.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0741678000
_diffrn_orient_matrix_UB_12      -0.0759383000
_diffrn_orient_matrix_UB_13      -0.0953803000
_diffrn_orient_matrix_UB_21      -0.1004561000
_diffrn_orient_matrix_UB_22      -0.1426283000
_diffrn_orient_matrix_UB_23      -0.0283123000
_diffrn_orient_matrix_UB_31      -0.1159953000
_diffrn_orient_matrix_UB_32      0.0393910000
_diffrn_orient_matrix_UB_33      -0.1118607000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21114
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.596
_diffrn_reflns_theta_min         4.296
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.718
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.133
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         3801
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0351
_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^)+(0.0432P)^2^+0.3358P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0909
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3345
_reflns_number_total             3801
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00795_si_003.cif
_cod_data_source_block           q022
_cod_database_code               4035603
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C24 H22 N2 O3'
_chemical_oxdiff_usercomment     Altmann_Koenig_LA017
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C5(H5A,H5B,H5C), C14(H14A,H14B,H14C), C12(H12A,H12B,H12C)
;
_olex2_date_sample_data_collection 2017-03-06
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems CryoStream 700'
_olex2_submission_original_sample_id LA_017
_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 1.328
_oxdiff_exptl_absorpt_empirical_full_min 0.812