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_4033599
_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         'C10 H7 N3'
_chemical_formula_sum            'C10 H7 N3'
_chemical_formula_weight         169.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-27
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.03.22 svn.r3403 for OlexSys, GUI svn.r5332)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.517(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.5514(3)
_cell_length_b                   9.5468(2)
_cell_length_c                   17.8087(5)
_cell_measurement_reflns_used    8253
_cell_measurement_temperature    296.95(10)
_cell_measurement_theta_max      73.5840
_cell_measurement_theta_min      5.1370
_cell_volume                     1564.70(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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      air
_diffrn_ambient_temperature      296.95(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 0.996
_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     -9.00  20.00   1.00    7.50    --   32.00  99.00-141.73   29
  2  \w     14.00 115.00   1.00    7.50    --   41.73  57.00 120.00  101
  3  \w      2.00  98.00   1.00    7.50    --   41.73-125.00-150.00   96
  4  \w     17.00 116.00   1.00    7.50    --   41.73  37.00 -90.00   99
  5  \w      2.00  98.00   1.00    7.50    --   41.73-125.00  30.00   96
  6  \w     17.00 116.00   1.00    7.50    --   41.73  37.00  30.00   99
  7  \w      7.00  33.00   1.00    7.50    --   44.00  89.00   7.85   26
  8  \w     19.00  46.00   1.00    7.50    --   52.00  80.00-117.45   27
  9  \w     18.00  46.00   1.00    7.50    --   52.00  81.00  80.14   28
 10  \w     19.00  46.00   1.00    7.50    --   52.00  80.00-166.65   27
 11  \w     19.00  46.00   1.00    7.50    --   52.00  80.00  -9.96   27
 12  \w     24.00 132.00   1.00    7.50    --   56.00  76.00 110.46  108
 13  \w     23.00  49.00   1.00    7.50    --   56.00  78.00 -78.15   26
 14  \w     23.00  49.00   1.00    7.50    --   56.00  78.00 170.53   26
 15  \w     31.00 140.00   1.00    7.50    --   64.00  77.00-124.58  109
 16  \w     36.00 113.00   1.00    7.50    --   68.00  75.00-110.46   77
 17  \w     94.00 143.00   1.00    7.50    --   68.00  76.00  11.84   49
 18  \w     36.00  62.00   1.00    7.50    --   68.00  76.00  11.84   26
 19  \w    100.00 133.00   1.00    7.50    --   68.00  77.00-173.54   33
 20  \w     35.00  87.00   1.00    7.50    --   68.00  77.00-173.54   52
 21  \w     39.00  75.00   1.00    7.50    --   72.00  77.00 124.79   36
 22  \w    113.00 139.00   1.00    7.50    --   72.00  77.00  77.70   26
 23  \w     40.00  65.00   1.00    7.50    --   72.00  77.00 -77.16   25
 24  \w     39.00  69.00   1.00    7.50    --   72.00  77.00 -42.18   30
 25  \w     39.00  66.00   1.00    7.50    --   72.00  77.00  77.70   27
 26  \w    113.00 148.00   1.00    7.50    --   72.00  76.00  44.96   35
 27  \w     40.00  66.00   1.00    7.50    --   72.00  76.00  44.96   26
 28  \w     74.00 145.00   1.00   12.50    --  106.46  77.00  60.00   71
 29  \w     31.00 100.00   1.00   12.50    --  106.46 -94.00  90.00   69
 30  \w     74.00 156.00   1.00   12.50    --  106.46  77.00-180.00   82
 31  \w     28.00  87.00   1.00   12.50    --  106.46 -94.00 -60.00   59
 32  \w     74.00 153.00   1.00   12.50    --  106.46  77.00 120.00   79
 33  \w     76.00 102.00   1.00   12.50    --  106.46  66.00 -62.00   26
 34  \w     76.00 144.00   1.00   12.50    --  106.46  77.00   0.00   68
 35  \w     25.00  89.00   1.00   12.50    --  106.46 -94.00 150.00   64
 36  \w     78.00 103.00   1.00   12.50    --  106.46  61.00-120.00   25
 37  \w    103.00 157.00   1.00   12.50    --  106.46  77.00-120.00   54
 38  \w     74.00 100.00   1.00   12.50    --  106.46  77.00-120.00   26
 39  \w     41.00  68.00   1.00   12.50    --  106.46 -45.00 -90.00   27
 40  \w     33.00 115.00   1.00   12.50    --  106.46-125.00-120.00   82
 41  \w     74.00 138.00   1.00   12.50    --  106.46  77.00 -60.00   64
 42  \w     33.00  76.00   1.00   12.50    --  106.46 -45.00 120.00   43
 43  \w     41.00  67.00   1.00   12.50    --  106.46 -45.00   0.00   26
 44  \w     42.00  73.00   1.00   12.50    --  106.46 -45.00-150.00   31
 45  \w     30.00 103.00   1.00   12.50    --  106.46 -94.00  30.00   73
 46  \w     74.00 103.00   1.00   12.50    --  106.46  77.00 -90.00   29
 47  \w     74.00 100.00   1.00   12.50    --  106.46  77.00 -30.00   26
 48  \w     42.00 121.00   1.00   12.50    --  106.46-125.00  30.00   79
 49  \w     78.00 105.00   1.00   12.50    --  106.46  61.00  90.00   27
 50  \w     24.00 105.00   1.00   12.50    --  106.46 -94.00-120.00   81
 51  \w     74.00 149.00   1.00   12.50    --  106.46  77.00 150.00   75
 52  \w     85.00 149.00   1.00   12.50    --  106.46 125.00-120.00   64
 53  \w     74.00 153.00   1.00   12.50    --  106.46  77.00  30.00   79
 54  \w     80.00 107.00   1.00   12.50    --  106.46  61.00   0.00   27
 55  \w    107.00 150.00   1.00   12.50    --  106.46  77.00-150.00   43
 56  \w     74.00  99.00   1.00   12.50    --  106.46  77.00-150.00   25
 57  \w     78.00 158.00   1.00   12.50    --  106.46  61.00 -30.00   80
 58  \w     74.00 155.00   1.00   12.50    --  106.46  77.00  90.00   81
 59  \w     77.00 109.00   1.00   12.50    --  106.46  61.00 -90.00   32
;
_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      -0.1607987000
_diffrn_orient_matrix_UB_12      -0.0211714000
_diffrn_orient_matrix_UB_13      -0.0442666000
_diffrn_orient_matrix_UB_21      0.0079163500
_diffrn_orient_matrix_UB_22      0.1277557500
_diffrn_orient_matrix_UB_23      -0.0515468000
_diffrn_orient_matrix_UB_31      0.0458188500
_diffrn_orient_matrix_UB_32      -0.0962634500
_diffrn_orient_matrix_UB_33      -0.0586924000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0102
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14499
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.833
_diffrn_reflns_theta_min         5.155
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (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 orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.285
_exptl_crystal_size_mid          0.115
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1590
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.201
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0252P)^2^+2.3469P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1086
_refine_ls_wR_factor_ref         0.1093
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1524
_reflns_number_total             1590
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02973_si_006.cif
_cod_data_source_block           c2_q037
_cod_depositor_comments
'Adding full bibliography for 4033594--4033599.cif.'
_cod_database_code               4033599
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C18 H4 N4'
_chemical_oxdiff_usercomment     Simeth_Koenig_NS-793-f3
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Sof(H003)=Sof(C008)=Sof(H008)=Sof(C00A)=Sof(N00C)=Sof(N00E)=Sof(C2)=Sof(H2)=
 Sof(C4)=Sof(H4)=Sof(C1AA)=Sof(H1AA)=1-FVAR(1)
 Sof(H004)=Sof(C007)=Sof(H007)=Sof(C009)=Sof(N00B)=Sof(N00D)=Sof(C1)=Sof(H1)=
 Sof(C0AA)=Sof(H0AA)=Sof(C3)=Sof(H3)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C003(H003), C004(H004), C005(H005), C006(H006), C007(H007), C008(H008),
 C1(H1), C2(H2), C4(H4), C0AA(H0AA), C1AA(H1AA), C3(H3)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems, CryoStream 700'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_original_sample_id NS_793_f3
_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 1.815
_oxdiff_exptl_absorpt_empirical_full_min 0.536