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_4033598
_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         'C15 H13 N3'
_chemical_formula_sum            'C15 H13 N3'
_chemical_formula_weight         235.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 99.1020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.87750(10)
_cell_length_b                   8.93220(10)
_cell_length_c                   17.6085(3)
_cell_measurement_reflns_used    10567
_cell_measurement_temperature    123.00(11)
_cell_measurement_theta_max      74.1540
_cell_measurement_theta_min      5.0600
_cell_volume                     1223.39(3)
_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_temperature      123.00(11)
_diffrn_detector_area_resol_mean 4.1818
_diffrn_detector_type            TitanS2
_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    -51.00  26.00   1.00    3.00    --  -44.08  40.00-134.00   77
  2  \w   -118.00  30.00   1.00    3.00    --  -44.08   0.00   0.00  148
  3  \w     21.00 115.00   1.00    3.00    --   44.08  38.00 -30.00   94
  4  \w     33.00 135.00   1.00   14.00    --  104.50 -77.00-150.00  102
  5  \w     27.00 141.00   1.00   14.00    --  104.50 -15.00 150.00  114
  6  \w     79.00 174.00   1.00   14.00    --  104.50  61.00 -90.00   95
  7  \w     33.00 121.00   1.00   14.00    --  104.50-125.00  60.00   88
  8  \w     82.00 173.00   1.00   14.00    --  104.50  45.00 120.00   91
  9  \w     81.00 177.00   1.00   14.00    --  104.50  30.00-180.00   96
 10  \w     32.00  91.00   1.00   14.00    --  104.50 -30.00  90.00   59
 11  \w     23.00 109.00   1.00   14.00    --  104.50 -94.00  60.00   86
 12  \w     34.00 130.00   1.00    3.00    --   44.08-178.00 150.00   96
 13  \w     20.00 113.00   1.00    3.00    --   44.08  57.00-150.00   93
 14  \w     81.00 177.00   1.00   14.00    --  104.50  30.00   0.00   96
 15  \w     82.00 173.00   1.00   14.00    --  104.50  45.00  60.00   91
 16  \w     23.00 109.00   1.00   14.00    --  104.50 -94.00 120.00   86
 17  \w     74.00 176.00   1.00   14.00    --  104.50  77.00   0.00  102
 18  \w     79.00 104.00   1.00   14.00    --  104.50  61.00 -60.00   25
 19  \w     74.00 176.00   1.00   14.00    --  104.50  77.00-150.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'GV1000, TitanS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14385
_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         74.295
_diffrn_reflns_theta_min         5.088
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.712
_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 orange'
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.069
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0421P)^2^+0.3584P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0840
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2349
_reflns_number_total             2463
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02973_si_003.cif
_cod_data_source_block           r011
_cod_depositor_comments
'Adding full bibliography for 4033594--4033599.cif.'
_cod_database_code               4033598
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
;
_shelx_res_checksum              22979
_shelx_hkl_checksum              58453
_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
;