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_4035602
_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 O2'
_chemical_formula_sum            'C24 H22 N2 O2'
_chemical_formula_weight         370.43
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-09
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                75.798(4)
_cell_angle_beta                 75.711(4)
_cell_angle_gamma                61.508(5)
_cell_formula_units_Z            2
_cell_length_a                   8.4787(4)
_cell_length_b                   8.6972(4)
_cell_length_c                   15.3983(7)
_cell_measurement_reflns_used    13186
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      73.7380
_cell_measurement_theta_min      5.8250
_cell_volume                     956.17(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.37b (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 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_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    2.50    --  -41.23 -37.00  60.00   99
  2  \w    -69.00  32.00   1.00    2.50    --  -41.23  57.00  30.00  101
  3  \w      2.00  97.00   1.00    2.50    --   41.23-125.00-120.00   95
  4  \w     13.00 114.00   1.00    2.50    --   41.23  57.00-120.00  101
  5  \w      7.00  33.00   1.00    2.50    --   44.00  89.00  97.21   26
  6  \w      9.00  35.00   1.00    2.50    --   44.00  86.00  10.94   26
  7  \w      9.00  35.00   1.00    2.50    --   44.00  86.00-113.35   26
  8  \w     18.00  45.00   1.00    2.50    --   52.00  81.00 -29.38   27
  9  \w     24.00 132.00   1.00    2.50    --   56.00  76.00 166.90  108
 10  \w     28.00 135.00   1.00    2.50    --   60.00  75.00 111.04  107
 11  \w     28.00 135.00   1.00    2.50    --   60.00  75.00 -16.78  107
 12  \w     32.00 139.00   1.00    2.50    --   64.00  75.00  67.85  107
 13  \w     32.00 140.00   1.00    2.50    --   64.00  76.00  14.70  108
 14  \w     36.00 144.00   1.00    2.50    --   68.00  76.00 -56.93  108
 15  \w     36.00 144.00   1.00    2.50    --   68.00  76.00 -92.18  108
 16  \w     36.00 143.00   1.00    2.50    --   68.00  75.00-130.50  107
 17  \w     36.00 144.00   1.00    2.50    --   68.00  76.00 176.50  108
 18  \w     43.00 144.00   1.00    2.50    --   72.00  61.00 113.66  101
 19  \w     54.00 153.00   1.00   10.00    --   80.00  48.00 178.69   99
 20  \w     66.00 158.00   1.00   10.00    --   96.00  68.00 -70.15   92
 21  \w     35.00 126.00   1.00   10.00    --  106.46 -61.00 150.00   91
 22  \w     84.00 109.00   1.00   10.00    --  106.46 -94.00 -30.00   25
 23  \w     32.00  93.00   1.00   10.00    --  106.46 -94.00   0.00   61
 24  \w     26.00  62.00   1.00   10.00    --  106.46 -94.00 -30.00   36
 25  \w     74.00 156.00   1.00   10.00    --  106.46  77.00 -60.00   82
 26  \w     77.00 158.00   1.00   10.00    --  106.46  61.00  60.00   81
 27  \w     81.00 108.00   1.00   10.00    --  106.46  61.00   0.00   27
 28  \w     24.00 107.00   1.00   10.00    --  106.46 -94.00 120.00   83
 29  \w    115.00 151.00   1.00   10.00    --  106.46  61.00-120.00   36
 30  \w     77.00 105.00   1.00   10.00    --  106.46  61.00-120.00   28
 31  \w     74.00 149.00   1.00   10.00    --  106.46  77.00 120.00   75
 32  \w    111.00 157.00   1.00   10.00    --  106.46  77.00 -30.00   46
 33  \w     74.00 100.00   1.00   10.00    --  106.46  77.00 -30.00   26
 34  \w     27.00  92.00   1.00   10.00    --  106.46 -94.00 -60.00   65
 35  \w     77.00 154.00   1.00   10.00    --  106.46  61.00 -90.00   77
 36  \w    112.00 146.00   1.00   10.00    --  106.46  77.00   0.00   34
 37  \w     34.00  72.00   1.00   10.00    --  106.46 -45.00  90.00   38
 38  \w     74.00 105.00   1.00   10.00    --  106.46  77.00   0.00   31
 39  \w     77.00 104.00   1.00   10.00    --  106.46  61.00  90.00   27
 40  \w     74.00 151.00   1.00   10.00    --  106.46  77.00-180.00   77
 41  \w     74.00 152.00   1.00   10.00    --  106.46  77.00 150.00   78
 42  \w     38.00  64.00   1.00   10.00    --  106.46 -45.00 -30.00   26
 43  \w     78.00 137.00   1.00   10.00    --  106.46  61.00  30.00   59
 44  \w    117.00 144.00   1.00   10.00    --  106.46  77.00  90.00   27
 45  \w     77.00 103.00   1.00   10.00    --  106.46  61.00 -30.00   26
 46  \w     31.00  98.00   1.00   10.00    --  106.46 -94.00  60.00   67
 47  \w     74.00 153.00   1.00   10.00    --  106.46  77.00  30.00   79
 48  \w     34.00  60.00   1.00   10.00    --  106.46 -45.00  30.00   26
 49  \w     75.00 113.00   1.00   10.00    --  106.46  77.00  90.00   38
 50  \w    105.00 146.00   1.00   10.00    --  106.46  77.00-150.00   41
 51  \w     73.00 121.00   1.00   10.00    --  106.46-125.00 -90.00   48
 52  \w     74.00 100.00   1.00   10.00    --  106.46  77.00-150.00   26
 53  \w     34.00  59.00   1.00   10.00    --  106.46-125.00 -90.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0314062000
_diffrn_orient_matrix_UB_12      -0.0350407000
_diffrn_orient_matrix_UB_13      -0.0861413000
_diffrn_orient_matrix_UB_21      0.1817975000
_diffrn_orient_matrix_UB_22      -0.0011412000
_diffrn_orient_matrix_UB_23      -0.0500991000
_diffrn_orient_matrix_UB_31      0.0985829000
_diffrn_orient_matrix_UB_32      -0.2008048000
_diffrn_orient_matrix_UB_33      0.0311976000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19807
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.597
_diffrn_reflns_theta_min         5.855
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.755
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.37b (Rigaku Oxford Diffraction, 2017)
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 light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       irregular
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.141
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3784
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0484P)^2^+0.2986P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0953
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3440
_reflns_number_total             3784
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00795_si_002.cif
_cod_data_source_block           r045
_cod_database_code               4035602
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C24 H22 N2 O2'
_chemical_oxdiff_usercomment     Simeth_Koenig_NS_fulgimide3
_reflns_odcompleteness_completeness 99.88
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C22(H22), C23(H23), C21(H21), C24(H24), C7(H7), C11(H11), C10(H10),
 C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C20(H20A,H20B,H20C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              66377
_shelx_hkl_checksum              98448
_olex2_date_sample_data_collection 2018-05-07
_olex2_date_sample_submission    2018-05-04
_olex2_diffrn_ambient_temperature_device 'Oxford cryosystem 700'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with inert oil'
_olex2_submission_original_sample_id 'NS_fulgimide 3'
_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 2.117
_oxdiff_exptl_absorpt_empirical_full_min 0.598