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_4033594
_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 F N3'
_chemical_formula_sum            'C14 H10 F N3'
_chemical_formula_weight         239.25
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-06
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                91.900(3)
_cell_angle_beta                 90.732(3)
_cell_angle_gamma                101.377(3)
_cell_formula_units_Z            4
_cell_length_a                   7.4944(3)
_cell_length_b                   11.0027(4)
_cell_length_c                   14.0513(5)
_cell_measurement_reflns_used    12414
_cell_measurement_temperature    122.99(10)
_cell_measurement_theta_max      76.4150
_cell_measurement_theta_min      4.0490
_cell_volume                     1135.04(7)
_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_environment      N~2~
_diffrn_ambient_temperature      122.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3546
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_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     -3.00  24.00   1.00    2.00    --   36.00  96.00 171.89   27
  2  \w    -74.00  35.00   1.00    2.00    --  -41.23  77.00  90.00  109
  3  \w   -116.00 -17.00   1.00    2.00    --  -41.23 -37.00  30.00   99
  4  \w    -97.00  -2.00   1.00    2.00    --  -41.23 125.00 120.00   95
  5  \w      2.00  97.00   1.00    2.00    --   41.23-125.00 -60.00   95
  6  \w     13.00 114.00   1.00    2.00    --   41.23  57.00-180.00  101
  7  \w      9.00  35.00   1.00    2.00    --   44.00  86.00 -95.01   26
  8  \w     15.00  46.00   1.00    2.00    --   48.00  80.00  -9.02   31
  9  \w     18.00  46.00   1.00    2.00    --   52.00  81.00 143.85   28
 10  \w     18.00  45.00   1.00    2.00    --   52.00  82.00  48.58   27
 11  \w     23.00 132.00   1.00    2.00    --   56.00  77.00 -82.34  109
 12  \w     27.00 136.00   1.00    2.00    --   60.00  77.00 112.27  109
 13  \w     31.00 140.00   1.00    2.00    --   64.00  77.00-132.82  109
 14  \w     32.00 140.00   1.00    2.00    --   64.00  76.00 -28.54  108
 15  \w     32.00 140.00   1.00    2.00    --   64.00  76.00-170.63  108
 16  \w     35.00 144.00   1.00    2.00    --   68.00  77.00 151.15  109
 17  \w     35.00 144.00   1.00    2.00    --   68.00  77.00 125.07  109
 18  \w     36.00 143.00   1.00    2.00    --   68.00  75.00  60.89  107
 19  \w     41.00 146.00   1.00    2.00    --   72.00  70.00 -60.37  105
 20  \w     40.00 147.00   1.00    2.00    --   72.00  75.00   2.13  107
 21  \w     52.00 158.00   1.00   10.00    --   84.00  74.00-178.83  106
 22  \w     79.00 158.00   1.00   10.00    --  112.00  77.00   0.00   79
 23  \w     40.00 141.00   1.00   10.00    --  112.00 -61.00  90.00  101
 24  \w     83.00 158.00   1.00   10.00    --  112.00  61.00   0.00   75
 25  \w     36.00 145.00   1.00   10.00    --  112.00 -77.00 -90.00  109
 26  \w     36.00 116.00   1.00   10.00    --  112.00-111.00  90.00   80
 27  \w     79.00 158.00   1.00   10.00    --  112.00  77.00 -90.00   79
 28  \w     86.00 158.00   1.00   10.00    --  112.00  45.00-180.00   72
 29  \w     79.00 158.00   1.00   10.00    --  112.00  77.00-150.00   79
 30  \w     79.00 146.00   1.00   10.00    --  112.00  77.00  60.00   67
 31  \w     37.00  77.00   1.00   10.00    --  112.00-111.00-120.00   40
 32  \w     84.00 142.00   1.00   10.00    --  112.00  61.00 120.00   58
 33  \w    128.00 153.00   1.00   10.00    --  112.00  77.00 -60.00   25
 34  \w     39.00  64.00   1.00   10.00    --  112.00 -45.00   0.00   25
 35  \w     38.00  68.00   1.00   10.00    --  112.00 -30.00 120.00   30
 36  \w     83.00 153.00   1.00   10.00    --  112.00  61.00  30.00   70
 37  \w     37.00  68.00   1.00   10.00    --  112.00 -30.00-120.00   31
 38  \w     93.00 157.00   1.00   10.00    --  112.00  61.00  90.00   64
 39  \w    130.00 158.00   1.00   10.00    --  112.00  77.00-120.00   28
 40  \w     79.00 105.00   1.00   10.00    --  112.00  77.00 -60.00   26
 41  \w     39.00  67.00   1.00   10.00    --  112.00 -45.00  90.00   28
 42  \w     79.00 121.00   1.00   10.00    --  112.00  77.00-120.00   42
 43  \w     83.00 116.00   1.00   10.00    --  112.00-111.00 -60.00   33
 44  \w     80.00 116.00   1.00   10.00    --  112.00-111.00-120.00   36
 45  \w     37.00  63.00   1.00   10.00    --  112.00-111.00 -60.00   26
 46  \w     80.00 109.00   1.00   10.00    --  112.00  77.00 120.00   29
 47  \w    127.00 157.00   1.00   10.00    --  112.00  77.00 120.00   30
 48  \w     81.00 157.00   1.00   10.00    --  112.00  77.00 -30.00   76
 49  \w     34.00  95.00   1.00   10.00    --  112.00 -94.00-120.00   61
 50  \w     79.00 105.00   1.00   10.00    --  112.00  77.00 150.00   26
 51  \w    120.00 146.00   1.00   10.00    --  112.00  77.00 150.00   26
 52  \w     79.00 116.00   1.00   10.00    --  112.00-111.00-180.00   37
 53  \w     41.00  67.00   1.00   10.00    --  112.00-111.00-180.00   26
 54  \w     71.00 115.00   1.00   10.00    --  112.00-111.00 120.00   44
 55  \w    132.00 158.00   1.00   10.00    --  112.00  77.00  30.00   26
 56  \w     87.00 113.00   1.00   10.00    --  112.00  61.00-150.00   26
 57  \w     79.00 105.00   1.00   10.00    --  112.00  77.00  30.00   26
 58  \w     36.00  68.00   1.00   10.00    --  112.00-111.00 120.00   32
 59  \w    122.00 155.00   1.00   10.00    --  112.00  61.00  60.00   33
 60  \w    128.00 156.00   1.00   10.00    --  112.00  77.00-180.00   28
 61  \w     84.00 118.00   1.00   10.00    --  112.00  61.00  60.00   34
 62  \w     86.00 114.00   1.00   10.00    --  112.00  61.00 -30.00   28
 63  \w    125.00 151.00   1.00   10.00    --  112.00  61.00-150.00   26
 64  \w     87.00 149.00   1.00   10.00    --  112.00  61.00 -60.00   62
 65  \w     79.00 105.00   1.00   10.00    --  112.00  77.00-180.00   26
 66  \w     84.00 110.00   1.00   10.00    --  112.00  61.00 -90.00   26
 67  \w     49.00 112.00   1.00   10.00    --  112.00-111.00   0.00   63
 68  \w    116.00 147.00   1.00   10.00    --  112.00  61.00-120.00   31
 69  \w     41.00  67.00   1.00   10.00    --  112.00 -30.00 -60.00   26
 70  \w     84.00 111.00   1.00   10.00    --  112.00  61.00-120.00   27
 71  \w     39.00  64.00   1.00   10.00    --  112.00 -45.00-150.00   25
 72  \w     54.00  80.00   1.00   10.00    --  112.00-111.00  30.00   26
 73  \w     88.00 114.00   1.00   10.00    --  112.00-111.00  30.00   26
 74  \w     37.00  62.00   1.00   10.00    --  112.00 -30.00 -30.00   25
 75  \w     36.00  62.00   1.00   10.00    --  112.00 -30.00 -90.00   26
;
_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      0.1191073000
_diffrn_orient_matrix_UB_12      -0.0137968000
_diffrn_orient_matrix_UB_13      -0.0867112000
_diffrn_orient_matrix_UB_21      -0.1366430000
_diffrn_orient_matrix_UB_22      -0.1174123000
_diffrn_orient_matrix_UB_23      -0.0342428000
_diffrn_orient_matrix_UB_31      -0.1054814000
_diffrn_orient_matrix_UB_32      0.0803088000
_diffrn_orient_matrix_UB_33      -0.0578536000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27447
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.550
_diffrn_reflns_theta_min         4.101
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.633
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (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 intense brown'
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4724
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0410
_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^)+(0.0668P)^2^+0.2555P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1177
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4186
_reflns_number_total             4724
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02973_si_005.cif
_cod_data_source_block           q152
_cod_depositor_comments
'Adding full bibliography for 4033594--4033599.cif.'
_cod_database_code               4033594
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C14 H10 F N3'
_chemical_oxdiff_usercomment     Simeth_Koenig_oF
_shelx_estimated_absorpt_t_max   0.897
_shelx_estimated_absorpt_t_min   0.835
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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), N6(H6), C13(H13), C14(H14), C23(H23), C12(H12), C2(H2), C10(H10),
 C11(H11), C16(H16), C28(H28), C3(H3A), C24(H24), C26(H26), C5(H5), C25(H25),
 C17(H17), C19(H19), C4(H4), C18(H18)
;
_shelx_res_checksum              84892
_shelx_hkl_checksum              44808
_olex2_date_sample_data_collection 2017-11-02
_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 2.636
_oxdiff_exptl_absorpt_empirical_full_min 0.453