A Photoswitchable Heteroditopic Ion-Pair Receptor.
Kokan, Zoran; Chmielewski, Michał J; Journal of the American Chemical Society 140 (2018) 16010–16014; doi:10.1021/jacs.8b08689

data_4133139
_publ_section_title
;
 A Photoswitchable Heteroditopic Ion-Pair Receptor.
;
_journal_issue                   47
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16010
_journal_page_last               16014
_journal_paper_doi               10.1021/jacs.8b08689
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H17 N5 O2'
_chemical_formula_sum            'C20 H17 N5 O2'
_chemical_formula_weight         359.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-08-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4964(2)
_cell_length_b                   20.5023(3)
_cell_length_c                   5.05085(7)
_cell_measurement_reflns_used    10850
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.7230
_cell_measurement_theta_min      3.4040
_cell_volume                     1708.27(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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     10.00  42.00   1.00    2.25    --    0.00  57.00   0.00   32
  2  \w     44.00  80.00   1.00    2.25    --    0.00  57.00   0.00   36
  3  \w     58.00  98.00   1.00    2.25    --    0.00  77.00 150.00   40
  4  \w    -40.00 -14.00   1.00    2.25    --    0.00  57.00   0.00   26
  5  \w    -38.00  38.00   1.00    2.25    --    0.00  77.00 150.00   76
  6  \w    -95.00 -36.00   1.00    2.25    --    0.00-178.00-120.00   59
  7  \w     79.00 147.00   1.00    9.00    --   54.96  77.00 120.00   68
  8  \w    102.00 138.00   1.00    9.00    --   54.96 125.00 150.00   36
  9  \w    115.00 142.00   1.00    9.00    --   54.96 125.00  30.00   27
 10  \w    117.00 144.00   1.00    9.00    --   54.96 125.00-150.00   27
 11  \w    107.00 136.00   1.00    9.00    --   54.96  77.00-150.00   29
 12  \w     71.00 145.00   1.00    9.00    --   54.96  57.00-180.00   74
 13  \w     70.00 142.00   1.00    9.00    --   54.96  77.00  60.00   72
 14  \w     13.00  40.00   1.00    9.00    --   54.96  77.00 120.00   27
 15  \w     12.00  38.00   1.00    9.00    --   54.96  82.00 155.22   26
 16  \w     13.00  67.00   1.00    9.00    --   54.96  77.00  60.00   54
 17  \w     13.00 153.00   1.00    9.00    --   54.96  77.00   0.00  140
 18  \w     15.00  41.00   1.00    9.00    --   54.96  77.00-150.00   26
 19  \w     13.00 152.00   1.00    9.00    --   54.96  77.00-120.00  139
 20  \w     24.00 120.00   1.00    9.00    --   54.96-125.00-150.00   96
 21  \w     13.00 135.00   1.00    9.00    --   54.96  77.00 -60.00  122
 22  \w     15.00  55.00   1.00    9.00    --   54.96  57.00-180.00   40
 23  \w    124.00 151.00   1.00   40.00    --  109.92  77.00 150.00   27
 24  \w    110.00 178.00   1.00   40.00    --  109.92  63.00  30.00   68
 25  \w    106.00 178.00   1.00   40.00    --  109.92  77.00 -60.00   72
 26  \w    150.00 178.00   1.00   40.00    --  109.92  77.00-120.00   28
 27  \w    147.00 174.00   1.00   40.00    --  109.92  64.00-132.34   27
 28  \w     70.00 178.00   1.00   40.00    --  109.92  59.00-155.09  108
 29  \w     69.00 104.00   1.00   40.00    --  109.92  68.00  37.69   35
 30  \w     68.00 163.00   1.00   40.00    --  109.92  77.00  60.00   95
 31  \w     68.00  97.00   1.00   40.00    --  109.92  66.00 -89.16   29
 32  \w     68.00 141.00   1.00   40.00    --  109.92  77.00-120.00   73
 33  \w     68.00 173.00   1.00   40.00    --  109.92  72.00  -1.97  105
 34  \w     68.00 144.00   1.00   40.00    --  109.92  71.00 179.75   76
 35  \w     68.00 108.00   1.00   40.00    --  109.92  77.00 150.00   40
 36  \w     68.00 175.00   1.00   40.00    --  109.92  77.00  90.00  107
 37  \w     67.00 121.00   1.00   40.00    --  109.92  64.00-132.34   54
 38  \w     67.00 162.00   1.00   40.00    --  109.92  63.00 -30.00   95
 39  \w     68.00 160.00   1.00   40.00    --  109.92  77.00 -90.00   92
 40  \w     68.00 100.00   1.00   40.00    --  109.92  77.00 -60.00   32
 41  \w     68.00  94.00   1.00   40.00    --  109.92  77.00 -30.00   26
 42  \w     67.00  93.00   1.00   40.00    --  109.92  63.00  30.00   26
 43  \w     68.00  94.00   1.00   40.00    --  109.92  71.00  53.77   26
 44  \w     71.00  98.00   1.00   40.00    --  109.92  63.00  90.00   27
 45  \w     67.00 177.00   1.00   40.00    --  109.92  63.00 134.45  110
 46  \w     68.00  93.00   1.00   40.00    --  109.92  63.00 150.00   25
 47  \w     68.00  94.00   1.00   40.00    --  109.92  67.00 -58.06   26
 48  \w     64.00 142.00   1.00   40.00    --  109.92 -77.00-150.00   78
 49  \w     48.00 112.00   1.00   40.00    --  109.92-111.00-150.00   64
 50  \w     42.00 115.00   1.00   40.00    --  109.92-111.00  30.00   73
 51  \w     24.00  58.00   1.00   40.00    --  109.92 -77.00-150.00   34
 52  \w     24.00 141.00   1.00   40.00    --  109.92 -77.00  30.00  117
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0552296000
_diffrn_orient_matrix_UB_12      -0.0594217000
_diffrn_orient_matrix_UB_13      0.0482228000
_diffrn_orient_matrix_UB_21      0.0574220000
_diffrn_orient_matrix_UB_22      -0.0428010000
_diffrn_orient_matrix_UB_23      -0.1663825000
_diffrn_orient_matrix_UB_31      0.0486867000
_diffrn_orient_matrix_UB_32      -0.0170012000
_diffrn_orient_matrix_UB_33      0.2509246000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            21290
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         3.439
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.769
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.724
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1219 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3033
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0287
_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^)+(0.0407P)^2^+0.1936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0733
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2876
_reflns_number_total             3033
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b08689_si_008.cif
_cod_data_source_block           again2
_cod_database_code               4133139
_chemical_oxdiff_formula         'C20 H17 N5 O2'
_chemical_oxdiff_usercomment     '100 K'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20)
;
_shelx_shelxl_version_number     2014/7
_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 1.766
_oxdiff_exptl_absorpt_empirical_full_min 0.398