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_4038555
_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         '4(H2 O), 6(N O3), C54 H72 N14'
_chemical_formula_sum            'C54 H80 N20 O22'
_chemical_formula_weight         1361.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-04-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_cell_angle_alpha                86.159(4)
_cell_angle_beta                 89.162(4)
_cell_angle_gamma                85.312(4)
_cell_formula_units_Z            2
_cell_length_a                   9.8128(4)
_cell_length_b                   16.7440(8)
_cell_length_c                   20.0298(11)
_cell_measurement_reflns_used    7554
_cell_measurement_temperature    153.00(10)
_cell_measurement_theta_max      63.5060
_cell_measurement_theta_min      3.3300
_cell_volume                     3272.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_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 0.955
_diffrn_measured_fraction_theta_max 0.955
_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   -113.00 -18.00   1.00    3.47    --  -42.18 -38.00-180.00   95
  2  \w    -67.00  32.00   1.00    3.47    --  -42.18  38.00   0.00   99
  3  \w     21.00 113.00   1.00   13.89    --   87.05 -45.00 -30.00   92
  4  \w     19.00 120.00   1.00   13.89    --   87.05 -77.00-150.00  101
  5  \w     99.00 160.00   1.00   13.89    --   87.05 125.00-120.00   61
  6  \w     58.00 118.00   1.00   13.89    --   87.05-125.00-150.00   60
  7  \w     11.00 110.00   1.00   13.89    --   87.05 -94.00   0.00   99
  8  \w     63.00 159.00   1.00   13.89    --   87.05  45.00-180.00   96
  9  \w     14.00 134.00   1.00   13.89    --   87.05 -15.00-180.00  120
;
_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      -0.0203244000
_diffrn_orient_matrix_UB_12      0.0087369000
_diffrn_orient_matrix_UB_13      -0.0763385000
_diffrn_orient_matrix_UB_21      0.0889241000
_diffrn_orient_matrix_UB_22      -0.0791922000
_diffrn_orient_matrix_UB_23      -0.0072044000
_diffrn_orient_matrix_UB_31      -0.1284323000
_diffrn_orient_matrix_UB_32      -0.0470297000
_diffrn_orient_matrix_UB_33      0.0079625000
_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  0.0341
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17910
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        63.813
_diffrn_reflns_theta_max         63.813
_diffrn_reflns_theta_min         3.565
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.920
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90458
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
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    1.382
_exptl_crystal_description       plate
_exptl_crystal_F_000             1440
_exptl_crystal_recrystallization_method
'The material was recrystallised from ? by solvent layering'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.569
_refine_diff_density_min         -1.043
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     881
_refine_ls_number_reflns         10331
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      9.009
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0731
_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^)+(0.1153P)^2^+4.8251P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1953
_refine_ls_wR_factor_ref         0.2126
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8190
_reflns_number_total             10331
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01260_si_002.cif
_cod_data_source_block           19kat_ek03
_cod_database_code               4038555
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C54 H66 N14 O'
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.789
_reflns_odcompleteness_completeness 98.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O601-N600_$1 \\sim O605_$1-N600_$1 \\sim O604_$1-N600_$1 \\sim O606_$1-N600_$1
\\sim O602_$1-
 N600_$1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O606) = Uanis(O605) = Uanis(O601) = Uanis(O604) = Uanis(O603)
4. Others
 Sof(O602)=Sof(O604)=Sof(O605)=1-FVAR(1)
 Sof(O601)=Sof(O603)=Sof(O606)=FVAR(1)
5.a Free rotating group:
 O100(H10G,H10H), O200(H20A,H20B), O400(H40A,H40B), O700(H70A,H70B)
5.b Secondary CH2 refined with riding coordinates:
 N3A(H3AA,H3AB), N3B(H3BA,H3BB), N3C(H3CA,H3CB), N8A(H8AA,H8AB), N8B(H8BA,
 H8BB), N8C(H8CA,H8CB), C1A(H1AA,H1AB), C1B(H1BA,H1BB), C1C(H1CA,H1CB),
 C2A(H2AA,H2AB), C2B(H2BA,H2BB), C2C(H2CA,H2CB), C4A(H4AA,H4AB), C4B(H4BA,H4BB),
  C4C(H4CA,H4CB), C7A(H7AA,H7AB), C7B(H7BA,H7BB), C7C(H7CA,H7CB), C9A(H9AA,
 H9AB), C9B(H9BA,H9BB), C9C(H9CA,H9CB), C10A(H10A,H10B), C10B(H10C,H10D),
 C10C(H10E,H10F)
5.c Aromatic/amide H refined with riding coordinates:
 C12A(H12A), C12B(H12B), C12C(H12C), C13A(H13A), C13B(H13B), C13C(H13C),
 C15A(H15A), C15B(H15B), C15C(H15C), C16A(H16A), C16B(H16B), C16C(H16C),
 C22A(H22A), C22B(H22B), C22C(H22C), C23A(H23A), C23B(H23B), C23C(H23C),
 C25A(H25A), C25B(H25B), C25C(H25C), C26A(H26A), C26B(H26B), C26C(H26C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_date_sample_data_collection 2019-06-27
_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 1.158
_oxdiff_exptl_absorpt_empirical_full_min 0.639