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_4133138
_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_formula_moiety         'C20 H17 N5 O2, H4 N, Br'
_chemical_formula_sum            'C20 H21 Br N6 O2'
_chemical_formula_weight         457.34
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-04-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 111.514(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.1019(7)
_cell_length_b                   7.5385(2)
_cell_length_c                   27.2240(8)
_cell_measurement_reflns_used    6180
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.4920
_cell_measurement_theta_min      3.2980
_cell_volume                     4029.0(2)
_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)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_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_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      0.0117450000
_diffrn_orient_matrix_UB_12      -0.0107134000
_diffrn_orient_matrix_UB_13      -0.0525066000
_diffrn_orient_matrix_UB_21      -0.0763511000
_diffrn_orient_matrix_UB_22      -0.0377296000
_diffrn_orient_matrix_UB_23      -0.0295116000
_diffrn_orient_matrix_UB_31      -0.0137817000
_diffrn_orient_matrix_UB_32      0.2006730000
_diffrn_orient_matrix_UB_33      -0.0083260000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13885
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         2.287
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.030
_exptl_absorpt_correction_T_max  0.828
_exptl_absorpt_correction_T_min  0.722
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.508
_exptl_crystal_description       needle
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.849
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         7170
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0453P)^2^+0.5838P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0931
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5941
_reflns_number_total             7170
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b08689_si_006.cif
_cod_data_source_block           2018_04_19_dt_zk50-nh4br_n
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4133138
_reflns_odcompleteness_completeness 99.92
_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,H,H) groups, All N(H,H,H,H)
  groups
2. Restrained distances
 N6A-H6AA
 0.87 with sigma of 0.02
 N6A-H6AB
 0.87 with sigma of 0.02
 N6A-H6AC
 0.87 with sigma of 0.02
 N6A-H6AD
 0.87 with sigma of 0.02
 N3B-H3BA
 0.87 with sigma of 0.02
 N3A-H3AA
 0.87 with sigma of 0.02
 N2A-H2AA
 0.87 with sigma of 0.02
 N2B-H2BA
 0.87 with sigma of 0.02
 N6B-H6BD
 0.87 with sigma of 0.02
 N6B-H6BA
 0.87 with sigma of 0.02
 N6B-H6BC
 0.87 with sigma of 0.02
 N6B-H6BB
 0.87 with sigma of 0.02
 H6AD-H6AC
 1.44 with sigma of 0.04
 H6AD-H6AB
 1.44 with sigma of 0.04
 H6AD-H6AC
 1.44 with sigma of 0.04
 H6AD-H6AA
 1.44 with sigma of 0.04
 H6AD-H6AC
 1.44 with sigma of 0.04
 H6AA-H6AB
 1.44 with sigma of 0.04
 H6AB-H6AD
 1.44 with sigma of 0.04
 H6AD-H6AB
 1.44 with sigma of 0.04
 H6AD-H6AA
 1.44 with sigma of 0.04
 H6BA-H6BB
 1.44 with sigma of 0.04
 H6BB-H6BC
 1.44 with sigma of 0.04
 H6BA-H6BC
 1.44 with sigma of 0.04
 H6BB-H6BD
 1.44 with sigma of 0.04
 H6BD-H6BA
 1.44 with sigma of 0.04
 H6BC-H6BD
 1.44 with sigma of 0.04
 H6AD-H6AC
 1.44 with sigma of 0.04
 H6AD-H6AA
 1.44 with sigma of 0.04
 H6AC-H6AA
 1.44 with sigma of 0.04
3.a Secondary CH2 refined with riding coordinates:
 C7A(H7AA,H7AB), C7B(H7BA,H7BB)
3.b Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C4A(H4A), C9A(H9A), C10A(H10A), C11A(H11A), C12A(H12A),
 C13A(H13A), C15A(H15A), C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A),
 C2B(H2B), C3B(H3B), C4B(H4B), C9B(H9B), C10B(H10B), C11B(H11B), C12B(H12B),
 C13B(H13B), C15B(H15B), C17B(H17B), C18B(H18B), C19B(H19B), C20B(H20B)
;
_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 1.309
_oxdiff_exptl_absorpt_empirical_full_min 0.677