Control of Photoisomerization of an Azoazacryptand by Anion Binding and Cucurbit[8]uril Encapsulation in an Aqueous Solution.
Oshchepkov, Aleksandr S.; Namashivaya, Siva S. R.; Khrustalev, Victor N.; Hampel, Frank; Laikov, Dimitri N.; Kataev, Evgeny A.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01260

data_4038556
_publ_section_title
;
 Control of Photoisomerization of an Azoazacryptand by Anion Binding and
 Cucurbit[8]uril Encapsulation in an Aqueous Solution.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01260
_journal_year                    2020
_chemical_formula_moiety         'C54 H66 N14'
_chemical_formula_sum            'C54 H66 N14'
_chemical_formula_weight         911.20
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-01-20
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 125.694(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.2762(8)
_cell_length_b                   9.56370(10)
_cell_length_c                   24.9579(8)
_cell_measurement_reflns_used    4665
_cell_measurement_temperature    153.00(10)
_cell_measurement_theta_max      72.3520
_cell_measurement_theta_min      3.4860
_cell_volume                     4899.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      153.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6144
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.961
_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   -116.00 -35.00   1.00    8.29    --  -42.70 -38.00   0.00   81
  2  \w   -109.00 -18.00   1.00    8.29    --  -42.70 -38.00 -90.00   91
  3  \w     76.00 178.00   1.00   33.15    --  104.05  30.00 -60.00  102
  4  \w    106.00 177.00   1.00   33.15    --  104.05 125.00 120.00   71
  5  \w     27.00 110.00   1.00   33.15    --  104.05 -94.00  60.00   83
  6  \w     43.00 130.00   1.00   33.15    --  104.05 -45.00 120.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0491177000
_diffrn_orient_matrix_UB_12      -0.0560941000
_diffrn_orient_matrix_UB_13      0.0123398000
_diffrn_orient_matrix_UB_21      -0.0554141000
_diffrn_orient_matrix_UB_22      0.0177318000
_diffrn_orient_matrix_UB_23      -0.0738251000
_diffrn_orient_matrix_UB_31      0.0118999000
_diffrn_orient_matrix_UB_32      -0.1499690000
_diffrn_orient_matrix_UB_33      -0.0133639000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            7799
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.261
_diffrn_reflns_theta_min         3.956
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.530
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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 yellowish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       plate
_exptl_crystal_F_000             1952
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of TCM and methanol  by solvent layering'
_exptl_crystal_size_max          0.344
_exptl_crystal_size_mid          0.265
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4661
_refine_ls_number_restraints     29
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0504
_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^)+(0.0750P)^2^+3.3168P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1317
_refine_ls_wR_factor_ref         0.1370
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4162
_reflns_number_total             4661
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01260_si_004.cif
_cod_data_source_block           19kat_ek02
_cod_original_cell_volume        4899.8(3)
_cod_database_code               4038556
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N'
_chemical_oxdiff_usercomment     'Probe DAZ'
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.821
_reflns_odcompleteness_completeness 98.97
_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) groups, All N(H) groups,
  All N(H,H) groups
2. Restrained distances
 N3-C3 \\sim N3-C5A \\sim N3-C4 \\sim N3-C3A \\sim N3-C5 \\sim N3-C4A
 with sigma of 0.02
 N7-C8 \\sim N7A-C8
 with sigma of 0.02
 N2-C1 \\sim N2A-C1 \\sim N4-C7 \\sim N4A-C7
 with sigma of 0.02
 N2-C2 \\sim N2A-C2 \\sim N4-C6 \\sim N4A-C6
 with sigma of 0.02
 N7-C9 \\sim N7A-C9
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C5A) = Uanis(C4)
Uanis(C5) = Uanis(C3A)
Uanis(C3) = Uanis(C4A)
Uanis(N2A) = Uanis(N2)
Uanis(N7) = Uanis(N7A)
Uanis(N4A) = Uanis(N4)
4. Others
 Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C5A)=Sof(H5AA)=
 Sof(H5AB)=1-FVAR(1)
 Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C4)=Sof(H4B)=Sof(H4C)=Sof(C5)=Sof(H5A)=Sof(H5B)=
 FVAR(1)
 Sof(N2A)=Sof(H2A)=Sof(N4A)=Sof(H4A)=Sof(N7A)=Sof(H7A)=Sof(H1BC)=Sof(H1BD)=
 Sof(H2BC)=Sof(H2BD)=Sof(H6BC)=Sof(H6BD)=Sof(H7BC)=Sof(H7BD)=Sof(H8BC)=
 Sof(H8BD)=Sof(H9BC)=Sof(H9BD)=1-FVAR(2)
 Sof(N2)=Sof(H2)=Sof(N4)=Sof(H4)=Sof(N7)=Sof(H7)=Sof(H1AA)=Sof(H1AB)=Sof(H2AA)=
 Sof(H2AB)=Sof(H6AA)=Sof(H6AB)=Sof(H7AA)=Sof(H7AB)=Sof(H8AA)=Sof(H8AB)=
 Sof(H9AA)=Sof(H9AB)=FVAR(2)
5.a Riding coordinates:
 N2(H2), N2A(H2A), N4(H4), N7A(H7A)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1AA,H1AB), C1(H1BC,H1BD), C2(H2AA,H2AB), C2(H2BC,H2BD), C3(H3A,H3B),
 C3A(H3AA,H3AB), C4(H4B,H4C), C4A(H4AA,H4AB), C5(H5A,H5B), C5A(H5AA,H5AB),
 C6(H6AA,H6AB), C6(H6BC,H6BD), C7(H7AA,H7AB), C7(H7BC,H7BD), C8(H8AA,H8AB),
 C8(H8BC,H8BD), C9(H9AA,H9AB), C9(H9BC,H9BD)
5.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16), C22(H22), C23(H23), C25(H25),
 C26(H26), C32(H32), C33(H33), C35(H35), C36(H36)
;
_olex2_date_sample_data_collection 2019-06-17
_olex2_diffrn_ambient_temperature_device 'Oxford Instruments Cryojet'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop in perfluoroether oil'
_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 1.098
_oxdiff_exptl_absorpt_empirical_full_min 0.878