Substituent Effects on 3-Arylazoindole Photoswitches.
Simeth, Nadja A.; Bellisario, Alfredo; Crespi, Stefano; Fagnoni, Maurizio; König, Burkhard; The Journal of organic chemistry 84 (2019) 6565–6575; doi:10.1021/acs.joc.8b02973

data_4033596
_publ_section_title
;
 Substituent Effects on 3-Arylazoindole Photoswitches.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6565
_journal_page_last               6575
_journal_paper_doi               10.1021/acs.joc.8b02973
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C14 H11 N3 O'
_chemical_formula_sum            'C14 H11 N3 O'
_chemical_formula_weight         237.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2018-06-20
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.411(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1456(4)
_cell_length_b                   5.1912(2)
_cell_length_c                   16.5884(5)
_cell_measurement_reflns_used    4378
_cell_measurement_temperature    123(1)
_cell_measurement_theta_max      73.3050
_cell_measurement_theta_min      5.3100
_cell_volume                     1131.99(7)
_computing_cell_refinement       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.42b (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_temperature      123(1)
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_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   -115.00 -11.00   1.00    5.50    --  -41.08 -57.00  30.00  104
  2  \w   -120.00  -7.00   1.00    5.50    --  -41.08 -77.00   0.00  113
  3  \w   -115.00 -11.00   1.00    5.50    --  -41.08 -57.00 120.00  104
  4  \w    -67.00  35.00   1.00    5.50    --  -41.08  37.00-180.00  102
  5  \w   -115.00 -13.00   1.00    5.50    --  -41.08 -57.00 150.00  102
  6  \w   -114.00 -19.00   1.00    5.50    --  -41.08 -57.00  90.00   95
  7  \w     23.00  55.00   1.00    5.50    --   41.08  57.00 120.00   32
  8  \w      8.00  81.00   1.00    5.50    --   41.08-125.00 -90.00   73
  9  \w     16.00  45.00   1.00    5.50    --   41.08  37.00  60.00   29
 10  \w      4.00  33.00   1.00    5.50    --   41.08  87.00 149.25   29
 11  \w     73.00  99.00   1.00   27.50    --  106.98  77.00  30.00   26
 12  \w     73.00  99.00   1.00   27.50    --  106.98  77.00  60.00   26
 13  \w     79.00 105.00   1.00   27.50    --  106.98  45.00  90.00   26
 14  \w     37.00  68.00   1.00   27.50    --  106.98 -30.00-120.00   31
 15  \w    108.00 156.00   1.00   27.50    --  106.98  77.00 120.00   48
 16  \w     84.00 134.00   1.00   27.50    --  106.98  45.00 120.00   50
 17  \w     98.00 158.00   1.00   27.50    --  106.98  61.00-120.00   60
 18  \w     73.00 103.00   1.00   27.50    --  106.98  77.00 120.00   30
 19  \w     77.00 102.00   1.00   27.50    --  106.98  61.00 150.00   25
 20  \w     77.00 103.00   1.00   27.50    --  106.98 -94.00  90.00   26
 21  \w     77.00 107.00   1.00   27.50    --  106.98  61.00-180.00   30
 22  \w     78.00 103.00   1.00   27.50    --  106.98  61.00  60.00   25
 23  \w     77.00 129.00   1.00   27.50    --  106.98  61.00  90.00   52
 24  \w     78.00 104.00   1.00   27.50    --  106.98  61.00  30.00   26
 25  \w     77.00 112.00   1.00   27.50    --  106.98  61.00 120.00   35
 26  \w     23.00  56.00   1.00   27.50    --  106.98 -94.00  90.00   33
 27  \w     73.00  99.00   1.00   27.50    --  106.98  77.00  90.00   26
 28  \w     80.00 106.00   1.00   27.50    --  106.98  45.00 150.00   26
 29  \w     34.00 127.00   1.00   27.50    --  106.98 -61.00   0.00   93
 30  \w     75.00 101.00   1.00   27.50    --  106.98  77.00-180.00   26
 31  \w     80.00 106.00   1.00   27.50    --  106.98  45.00-180.00   26
 32  \w     93.00 119.00   1.00   27.50    --  106.98-125.00-150.00   26
 33  \w     73.00 100.00   1.00   27.50    --  106.98  77.00   0.00   27
 34  \w    113.00 152.00   1.00   27.50    --  106.98  77.00-180.00   39
 35  \w     81.00 113.00   1.00   27.50    --  106.98  45.00  60.00   32
 36  \w     77.00 152.00   1.00   27.50    --  106.98  61.00-150.00   75
 37  \w     77.00 103.00   1.00   27.50    --  106.98  77.00-150.00   26
 38  \w     39.00  90.00   1.00   27.50    --  106.98-125.00-150.00   51
 39  \w     39.00  77.00   1.00   27.50    --  106.98 -94.00 -30.00   38
 40  \w    114.00 158.00   1.00   27.50    --  106.98  77.00 150.00   44
 41  \w     73.00  98.00   1.00   27.50    --  106.98  77.00 150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.496
_diffrn_reflns_theta_min         3.362
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.42b (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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.032
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         2269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0526P)^2^+0.2469P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0995
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1878
_reflns_number_total             2269
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02973_si_004.cif
_cod_data_source_block           p187
_cod_depositor_comments
'Adding full bibliography for 4033594--4033599.cif.'
_cod_database_code               4033596
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
;
_shelx_res_checksum              7975
_shelx_hkl_checksum              83830
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems CryoStream 700'
_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
;