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_4033597
_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 H10 Br N3'
_chemical_formula_sum            'C14 H10 Br N3'
_chemical_formula_weight         300.16
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-08-05
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.07.26 svn.r3321 for OlexSys, GUI svn.r5206)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.7408(2)
_cell_length_b                   10.8233(2)
_cell_length_c                   16.5350(2)
_cell_measurement_reflns_used    16783
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      76.3390
_cell_measurement_theta_min      5.3170
_cell_volume                     2459.10(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_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 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   -115.00 -11.00   1.00    1.00    --  -40.71 -57.00 -90.00  104
  2  \w   -122.00   6.00   1.00    1.00    --  -40.71 -19.00  30.00  128
  3  \w    -98.00  -2.00   1.00    1.00    --  -40.71 125.00-180.00   96
  4  \w    -98.00  -2.00   1.00    1.00    --  -40.71 125.00   0.00   96
  5  \w     14.00 117.00   1.00    1.00    --   40.71  37.00-150.00  103
  6  \w     35.00 116.00   1.00    5.00    --  113.00-111.00-150.00   81
  7  \w     29.00 109.00   1.00    5.00    --  113.00 -94.00-150.00   80
  8  \w     34.00 147.00   1.00    5.00    --  113.00 -77.00-120.00  113
  9  \w     35.00  69.00   1.00    5.00    --  113.00 -30.00 120.00   34
 10  \w     38.00  77.00   1.00    5.00    --  113.00 -45.00 -90.00   39
 11  \w     39.00 143.00   1.00    5.00    --  113.00 -61.00   0.00  104
 12  \w     35.00 116.00   1.00    5.00    --  113.00-111.00  30.00   81
 13  \w     29.00 109.00   1.00    5.00    --  113.00 -94.00-120.00   80
 14  \w     30.00 158.00   1.00    5.00    --  113.00 -15.00-180.00  128
 15  \w     35.00 116.00   1.00    5.00    --  113.00-111.00-180.00   81
 16  \w     35.00 116.00   1.00    5.00    --  113.00-111.00 -30.00   81
 17  \w     35.00  69.00   1.00    5.00    --  113.00 -30.00 -60.00   34
 18  \w     34.00 147.00   1.00    5.00    --  113.00 -77.00  30.00  113
 19  \w     35.00  69.00   1.00    5.00    --  113.00 -30.00 -90.00   34
 20  \w     85.00 158.00   1.00    5.00    --  113.00  45.00-150.00   73
 21  \w     39.00 143.00   1.00    5.00    --  113.00 -61.00  30.00  104
 22  \w     52.00 158.00   1.00    5.00    --  113.00  15.00 120.00  106
 23  \w     35.00 116.00   1.00    5.00    --  113.00-111.00-120.00   81
 24  \w     35.00 150.00   1.00    5.00    --  113.00 178.00-180.00  115
 25  \w     85.00 158.00   1.00    5.00    --  113.00  45.00-120.00   73
 26  \w     83.00 158.00   1.00    5.00    --  113.00  61.00  30.00   75
 27  \w     35.00 150.00   1.00    5.00    --  113.00 178.00-150.00  115
 28  \w     83.00 149.00   1.00    5.00    --  113.00  61.00  60.00   66
 29  \w    101.00 140.00   1.00    5.00    --  113.00 -77.00 -90.00   39
 30  \w     76.00 116.00   1.00    5.00    --  113.00-111.00  60.00   40
 31  \w     37.00  71.00   1.00    5.00    --  113.00 -77.00 -90.00   34
 32  \w     33.00 103.00   1.00    5.00    --  113.00 -94.00 -60.00   70
 33  \w     42.00  73.00   1.00    5.00    --  113.00-111.00 -60.00   31
 34  \w     80.00 110.00   1.00    5.00    --  113.00-111.00 -60.00   30
 35  \w    102.00 128.00   1.00    5.00    --  113.00  45.00 150.00   26
 36  \w    129.00 155.00   1.00    5.00    --  113.00  45.00 150.00   26
 37  \w     83.00 145.00   1.00    5.00    --  113.00  61.00-180.00   62
 38  \w     45.00  71.00   1.00    5.00    --  113.00 -45.00 120.00   26
 39  \w     67.00 104.00   1.00    5.00    --  113.00   8.00  74.50   37
 40  \w     61.00 112.00   1.00    5.00    --  113.00 -61.00 -90.00   51
 41  \w     84.00 116.00   1.00    5.00    --  113.00-111.00 150.00   32
 42  \w     36.00  69.00   1.00    5.00    --  113.00 -30.00  60.00   33
 43  \w     56.00 102.00   1.00    5.00    --  113.00 -59.00  88.53   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0889475000
_diffrn_orient_matrix_UB_12      0.0476430000
_diffrn_orient_matrix_UB_13      0.0474703000
_diffrn_orient_matrix_UB_21      0.0682493000
_diffrn_orient_matrix_UB_22      -0.0680894000
_diffrn_orient_matrix_UB_23      -0.0589807000
_diffrn_orient_matrix_UB_31      0.0035478000
_diffrn_orient_matrix_UB_32      0.1154977000
_diffrn_orient_matrix_UB_33      -0.0542790000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            40174
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         76.464
_diffrn_reflns_theta_min         5.350
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.419
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.936
_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            'clear brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2577
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0261
_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^)+(0.0395P)^2^+1.5169P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0726
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2390
_reflns_number_total             2577
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02973_si_002.cif
_cod_data_source_block           p120
_cod_depositor_comments
'Adding full bibliography for 4033594--4033599.cif.'
_cod_database_code               4033597
_chemical_oxdiff_formula         'C14 H10 Br1 N3'
_chemical_oxdiff_usercomment     Simeth_Koenig_NS_558_f1
_reflns_odcompleteness_completeness 98.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C9(H9), C14(H14), C10(H10), C3(H3A), C11(H11), C12(H12),
 C5(H5), C4(H4)
;
_shelx_res_checksum              11477
_shelx_hkl_checksum              79845
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-08-04
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems CryoStream 700'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with inert oil'
_olex2_submission_original_sample_id NS_558_f1
_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 1.515
_oxdiff_exptl_absorpt_empirical_full_min 0.635