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_4033595
_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         'C18 H12 N4'
_chemical_formula_sum            'C18 H12 N4'
_chemical_formula_weight         284.32
_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                 108.602(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.4932(3)
_cell_length_b                   10.3321(2)
_cell_length_c                   19.1214(4)
_cell_measurement_reflns_used    36951
_cell_measurement_temperature    123.0(2)
_cell_measurement_theta_max      73.9130
_cell_measurement_theta_min      3.3200
_cell_volume                     2713.75(10)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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      123.0(2)
_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      5.00  33.00   1.00    2.00    --   40.00  89.00  46.77   28
  2  \w   -115.00 -19.00   1.00    2.00    --  -43.14 -38.00 -30.00   96
  3  \w     19.00 115.00   1.00    2.00    --   43.14  38.00  30.00   96
  4  \w    -20.00  83.00   1.00    2.00    --   43.14 -99.00 -60.00  103
  5  \w     18.00 113.00   1.00    2.00    --   43.14  57.00-150.00   95
  6  \w    -27.00  69.00   1.00    2.00    --   43.14 -57.00  60.00   96
  7  \w     18.00 113.00   1.00    2.00    --   43.14  57.00 120.00   95
  8  \w     10.00  38.00   1.00    2.00    --   44.00  84.00 -55.39   28
  9  \w     19.00  46.00   1.00    2.00    --   52.00  81.00 -97.59   27
 10  \w     19.00  46.00   1.00    2.00    --   52.00  81.00  57.69   27
 11  \w     19.00  46.00   1.00    2.00    --   52.00  81.00 -23.55   27
 12  \w     19.00  45.00   1.00    2.00    --   52.00  82.00 134.38   26
 13  \w     20.00  46.00   1.00    2.00    --   52.00  80.00 105.01   26
 14  \w     19.00  45.00   1.00    2.00    --   52.00  82.00-151.63   26
 15  \w     28.00 134.00   1.00    2.00    --   60.00  77.00 143.28  106
 16  \w     32.00 138.00   1.00    2.00    --   64.00  77.00 -58.34  106
 17  \w     32.00 138.00   1.00    2.00    --   64.00  77.00  -5.94  106
 18  \w     40.00 146.00   1.00    2.00    --   72.00  77.00 177.54  106
 19  \w     41.00 146.00   1.00    2.00    --   72.00  76.00  42.56  105
 20  \w     40.00 146.00   1.00    2.00    --   72.00  77.00 -41.73  106
 21  \w     40.00 146.00   1.00    2.00    --   72.00  77.00-147.80  106
 22  \w     44.00 150.00   1.00   15.00    --   76.00  77.00-140.55  106
 23  \w     44.00 150.00   1.00   15.00    --   76.00  77.00-100.05  106
 24  \w     45.00 150.00   1.00   15.00    --   76.00  76.00  95.92  105
 25  \w     44.00 150.00   1.00   15.00    --   76.00  77.00 138.66  106
 26  \w     44.00 150.00   1.00   15.00    --   76.00  77.00  64.22  106
 27  \w     50.00 152.00   1.00   15.00    --   80.00  72.00 -20.76  102
 28  \w     50.00 152.00   1.00   15.00    --   80.00  71.00-113.59  102
 29  \w     49.00 153.00   1.00   15.00    --   80.00  75.00   4.21  104
 30  \w     54.00 112.00   1.00   15.00    --   84.00  71.00 172.68   58
 31  \w     58.00  84.00   1.00   15.00    --   88.00  76.00  40.46   26
 32  \w     61.00 161.00   1.00   15.00    --   92.00  75.00  93.97  100
 33  \w     68.00 156.00   1.00   15.00    --   96.00  66.00 134.06   88
 34  \w    104.00 150.00   1.00   15.00    --  104.50  77.00 150.00   46
 35  \w     73.00 101.00   1.00   15.00    --  104.50  77.00 150.00   28
 36  \w     47.00 121.00   1.00   15.00    --  104.50-125.00-150.00   74
 37  \w     73.00 159.00   1.00   15.00    --  104.50  77.00  60.00   86
 38  \w     23.00 107.00   1.00   15.00    --  104.50 -94.00 -30.00   84
 39  \w     74.00 138.00   1.00   15.00    --  104.50  77.00   0.00   64
 40  \w     38.00  97.00   1.00   15.00    --  104.50 -45.00  60.00   59
 41  \w     21.00 104.00   1.00   15.00    --  104.50 -94.00-120.00   83
 42  \w     73.00 177.00   1.00   15.00    --  104.50  77.00 -30.00  104
 43  \w     39.00 109.00   1.00   15.00    --  104.50 -94.00  60.00   70
 44  \w     74.00 156.00   1.00   15.00    --  104.50  77.00 -60.00   82
 45  \w     73.00 172.00   1.00   15.00    --  104.50  77.00-150.00   99
 46  \w     73.00 157.00   1.00   15.00    --  104.50  77.00-180.00   84
 47  \w     94.00 120.00   1.00   15.00    --  104.50 -61.00-180.00   26
 48  \w     41.00  68.00   1.00   15.00    --  104.50 -61.00-180.00   27
 49  \w     73.00 139.00   1.00   15.00    --  104.50  77.00-120.00   66
 50  \w     36.00  97.00   1.00   15.00    --  104.50 -45.00 -60.00   61
 51  \w     73.00 177.00   1.00   15.00    --  104.50  77.00  30.00  104
 52  \w     73.00 154.00   1.00   15.00    --  104.50  77.00 -90.00   81
;
_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  0.0802
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            66316
_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         73.966
_diffrn_reflns_theta_min         3.361
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18251
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       prism
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.417
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.124
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.00040(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     494
_refine_ls_number_reflns         5432
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0565P)^2^+0.5633P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4822
_reflns_number_total             5432
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02973_si_007.cif
_cod_data_source_block           nei
_cod_depositor_comments
'Adding full bibliography for 4033594--4033599.cif.'
_cod_database_code               4033595
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
;
_shelx_res_checksum              17365
_shelx_hkl_checksum              2044
_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
;