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_4035601
_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 H21 N O3'
_chemical_formula_sum            'C24 H21 N O3'
_chemical_formula_weight         371.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-12-20
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.12.08 svn.r3473 for OlexSys, GUI svn.r5433)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.4650(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6727(2)
_cell_length_b                   12.2092(2)
_cell_length_c                   15.0377(2)
_cell_measurement_reflns_used    22888
_cell_measurement_temperature    122.99(10)
_cell_measurement_theta_max      74.3230
_cell_measurement_theta_min      4.6710
_cell_volume                     1920.39(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      122.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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      5.00  57.00   0.50    6.00    --   45.95 -37.00 -30.00  104
  2  \w      5.00  86.00   0.50    6.00    --   45.95-111.00-142.00  162
  3  \w     74.00  99.00   0.50   24.00    --  100.00-111.00-142.00   50
  4  \w     81.00 107.00   0.50   24.00    --  100.00 -85.00-168.33   52
  5  \w     86.00 112.00   0.50   24.00    --  100.00-125.00 -90.00   52
  6  \w     87.00 112.00   0.50   24.00    --  100.00 -93.00 -27.27   50
  7  \w     96.00 121.00   0.50   24.00    --  100.00-125.00  30.00   50
  8  \w     84.00 110.00   0.50   24.00    --  100.00 -77.00  60.00   52
  9  \w    100.00 125.00   0.50   24.00    --  100.00 -89.00 106.71   50
 10  \w     69.00 106.00   0.50   24.00    --  100.00 -94.00  30.00   74
 11  \w     75.00 119.00   0.50   24.00    --  100.00-125.00 -30.00   88
 12  \w     64.00  90.00   0.50   24.00    --  100.00-125.00   0.00   52
 13  \w     62.00  87.00   0.50   24.00    --  100.00 -94.00   0.00   50
 14  \w     45.00  94.00   0.50   24.00    --  100.00 -94.00  60.00   98
 15  \w     57.00 117.00   0.50   24.00    --  100.00-125.00 120.00  120
 16  \w     71.00 120.00   0.50   24.00    --  100.00-125.00 150.00   98
 17  \w     50.00 104.00   0.50   24.00    --  100.00 -71.00 156.13  108
 18  \w     38.00  63.00   0.50   24.00    --  100.00 -77.00  60.00   50
 19  \w     43.00  69.00   0.50   24.00    --  100.00 -61.00 120.00   52
 20  \w     44.00  76.00   0.50   24.00    --  100.00 -45.00 150.00   64
 21  \w     37.00  62.00   0.50   24.00    --  100.00 -45.00  90.00   50
 22  \w     32.00  57.00   0.50   24.00    --  100.00 -30.00  60.00   50
 23  \w     28.00  53.00   0.50   24.00    --  100.00 -30.00 120.00   50
 24  \w     87.00 126.00   0.50   24.00    --  100.00  15.00 150.00   78
 25  \w     97.00 122.00   0.50   24.00    --  100.00  45.00 150.00   50
 26  \w    141.00 172.00   0.50   24.00    --  100.00  77.00  90.00   62
 27  \w    148.00 173.00   0.50   24.00    --  100.00  77.00  60.00   50
 28  \w    142.00 168.00   0.50   24.00    --  100.00 125.00  30.00   52
 29  \w    133.00 172.00   0.50   24.00    --  100.00  66.00  33.94   78
 30  \w    121.00 173.00   0.50   24.00    --  100.00  77.00   0.00  104
 31  \w    108.00 134.00   0.50   24.00    --  100.00 111.00 -47.00   52
 32  \w     98.00 124.00   0.50   24.00    --  100.00  66.00  33.94   52
 33  \w    108.00 145.00   0.50   24.00    --  100.00  30.00  60.00   74
 34  \w     95.00 166.00   0.50   24.00    --  100.00  45.00   0.00  142
 35  \w    114.00 172.00   0.50   24.00    --  100.00  45.00-120.00  116
 36  \w    131.00 170.00   0.50   24.00    --  100.00  30.00-150.00   78
 37  \w    101.00 127.00   0.50   24.00    --  100.00  15.00 -60.00   52
 38  \w     85.00 165.00   0.50   24.00    --  100.00  61.00 -60.00  160
 39  \w     83.00 139.00   0.50   24.00    --  100.00  76.00 -51.91  112
 40  \w     88.00 132.00   0.50   24.00    --  100.00  45.00  30.00   88
 41  \w     80.00 108.00   0.50   24.00    --  100.00  77.00   0.00   56
 42  \w     81.00 140.00   0.50   24.00    --  100.00  77.00  60.00  118
 43  \w     87.00 115.00   0.50   24.00    --  100.00  77.00  90.00   56
 44  \w     81.00 107.00   0.50   24.00    --  100.00 125.00  30.00   52
 45  \w     87.00 112.00   0.50   24.00    --  100.00  15.00 -90.00   50
 46  \w     88.00 124.00   0.50   24.00    --  100.00  30.00-150.00   72
 47  \w     73.00  99.00   0.50   24.00    --  100.00 -15.00-150.00   52
 48  \w     42.00  79.00   0.50   24.00    --  100.00 -45.00-180.00   74
 49  \w     51.00  78.00   0.50   24.00    --  100.00 -45.00-150.00   54
 50  \w     48.00 114.00   0.50   24.00    --  100.00 -61.00 -90.00  132
 51  \w     67.00 113.00   0.50   24.00    --  100.00-125.00-150.00   92
 52  \w     50.00  76.00   0.50   24.00    --  100.00 -94.00 -90.00   52
 53  \w     53.00 103.00   0.50   24.00    --  100.00 -94.00-120.00  100
 54  \w     37.00  65.00   0.50   24.00    --  100.00-111.00-142.00   56
 55  \w     45.00 121.00   0.50   24.00    --  100.00-125.00-180.00  152
 56  \w     43.00 108.00   0.50   24.00    --  100.00 -94.00 -60.00  130
 57  \w     28.00  59.00   0.50   24.00    --  100.00 -94.00  30.00   62
 58  \w     36.00  62.00   0.50   24.00    --  100.00-125.00  30.00   52
 59  \w     35.00  83.00   0.50   24.00    --  100.00-125.00  60.00   96
 60  \w     28.00  54.00   0.50   24.00    --  100.00-125.00 150.00   52
 61  \w    -19.00  41.00   0.50    6.00    --   45.95 -57.00 150.00  120
 62  \w     37.00  68.00   0.50   24.00    --  100.00 -30.00   0.00   62
 63  \w     32.00  58.00   0.50   24.00    --  100.00 -77.00 -90.00   52
 64  \w     28.00  53.00   0.50   24.00    --  100.00 -45.00-120.00   50
 65  \w     33.00  59.00   0.50   24.00    --  100.00 -61.00-180.00   52
 66  \w     28.00  60.00   0.50   24.00    --  100.00-125.00 -90.00   64
 67  \w     34.00  63.00   0.50   24.00    --  100.00-125.00 -30.00   58
 68  \w    -40.00 -14.00   0.50    6.00    --  -45.95 111.00 -47.00   52
 69  \w   -110.00 -44.00   0.50   24.00    --  -81.00 111.00 -47.00  132
 70  \w   -113.00 -43.00   0.50    6.00    --  -45.95 -57.00 120.00  140
 71  \w   -118.00 -72.00   0.50    6.00    --  -45.95-125.00   0.00   92
 72  \w   -118.00 -86.00   0.50    6.00    --  -45.95-125.00 -30.00   64
 73  \w   -119.00 -24.00   0.50    6.00    --  -45.95 -77.00  30.00  190
 74  \w   -141.00-116.00   0.50   24.00    --  -81.00-111.00-142.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1003618000
_diffrn_orient_matrix_UB_12      0.0109684000
_diffrn_orient_matrix_UB_13      -0.0602867000
_diffrn_orient_matrix_UB_21      -0.0305844000
_diffrn_orient_matrix_UB_22      0.1230182000
_diffrn_orient_matrix_UB_23      -0.0121674000
_diffrn_orient_matrix_UB_31      0.1033306000
_diffrn_orient_matrix_UB_32      0.0258977000
_diffrn_orient_matrix_UB_33      0.0845307000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            40249
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.682
_diffrn_reflns_theta_min         4.227
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.02599
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.165
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3936
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0400
_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^)+(0.0583P)^2^+0.5180P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1129
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3541
_reflns_number_total             3936
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00795_si_004.cif
_cod_data_source_block           q127
_cod_database_code               4035601
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C24 H31 N O3 '
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.896
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C5(H5), C2(H2), C4(H4), C3(H3), C14(H14), C12(H12),
 C13(H13)
2.b Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C18(H18A,H18B,H18C), C17(H17A,H17B,H17C), C27(H27A,H27B,
 H27C)
;
_olex2_date_sample_data_collection 2017-09-14
_olex2_date_sample_submission    2017-09-11
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a glass fibre with superglue'
_olex2_submission_original_sample_id NS-961
_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 29.830
_oxdiff_exptl_absorpt_empirical_full_min 0.677