Pressure-induced ratiometric signalling chemosensor. A case of helical anthracenes
Kinoshita, Tomokazu; Fujise, Kei; Tsurumaki, Eiji; Toyota, Shinji; Fukuhara, Gaku; Chemical Communications  (2022) –; doi:10.1039/D2CC00428C

data_7129705
_publ_section_title
;
 Pressure-induced ratiometric signalling chemosensor. A case of helical
 anthracenes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00428C
_journal_year                    2022
_chemical_formula_moiety         '2(C54 H30), 0.25(C H Cl3)'
_chemical_formula_sum            'C108.25 H60.25 Cl0.75'
_chemical_formula_weight         1387.40
_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     dual
_audit_creation_date             2022-01-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-01-20 deposited with the CCDC.	2022-02-11 downloaded from the CCDC.
;
_cell_angle_alpha                91.2040(10)
_cell_angle_beta                 99.3180(10)
_cell_angle_gamma                106.0350(10)
_cell_formula_units_Z            2
_cell_length_a                   12.8813(2)
_cell_length_b                   14.78750(10)
_cell_length_c                   19.0100(2)
_cell_measurement_reflns_used    22628
_cell_measurement_temperature    123
_cell_measurement_theta_max      76.3340
_cell_measurement_theta_min      3.6140
_cell_volume                     3426.00(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_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_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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    -24.00  44.00   0.50    0.58    --  -38.95  19.00  60.00  136
  2  \w    -24.00  43.00   0.50    0.58    --  -38.95  19.00 120.00  134
  3  \w    -39.00  41.00   0.50    0.58    --  -38.95  37.00   0.00  160
  4  \w    -15.00  11.00   0.50    0.58    --  -38.95  19.00-120.00   52
  5  \w    -24.00  43.00   0.50    0.58    --  -38.95  19.00 -90.00  134
  6  \w    -40.00  40.00   0.50    0.58    --  -38.95  37.00-180.00  160
  7  \w     66.00  98.00   0.50    0.58    --   38.95 145.00-116.00   64
  8  \w     86.00 130.00   0.50    2.32    --  113.00  45.00-120.00   88
  9  \w    137.00 175.00   0.50    2.32    --  113.00  45.00-120.00   76
 10  \w    114.00 178.00   0.50    2.32    --  113.00  61.00  30.00  128
 11  \w    142.00 172.00   0.50    2.32    --  113.00  30.00  90.00   60
 12  \w    129.00 155.00   0.50    2.32    --  113.00 126.00  75.00   52
 13  \w     88.00 114.00   0.50    2.32    --  113.00 126.00  75.00   52
 14  \w     95.00 141.00   0.50    2.32    --  113.00 111.00 120.00   92
 15  \w     84.00 174.00   0.50    2.32    --  113.00  30.00  30.00  180
 16  \w     80.00 135.00   0.50    2.32    --  113.00  30.00  90.00  110
 17  \w     55.00 106.00   0.50    2.32    --  113.00 -77.00 150.00  102
 18  \w     83.00 108.00   0.50    2.32    --  113.00-111.00  90.00   50
 19  \w     83.00 108.00   0.50    2.32    --  113.00 -77.00  90.00   50
 20  \w     72.00 103.00   0.50    2.32    --  113.00 -94.00  90.00   62
 21  \w     69.00 112.00   0.50    2.32    --  113.00-126.00  -1.00   86
 22  \w     82.00 108.00   0.50    2.32    --  113.00-111.00 -60.00   52
 23  \w     69.00 103.00   0.50    2.32    --  113.00 -94.00 -60.00   68
 24  \w     66.00 105.00   0.50    2.32    --  113.00-111.00-120.00   78
 25  \w    102.00 127.00   0.50    2.32    --  113.00-145.00-169.00   50
 26  \w     73.00 108.00   0.50    2.32    --  113.00-111.00-180.00   70
 27  \w     59.00  99.00   0.50    2.32    --  113.00 -77.00-120.00   80
 28  \w     45.00 104.00   0.50    2.32    --  113.00-111.00 -90.00  118
 29  \w     58.00  85.00   0.50    2.32    --  113.00 -94.00   0.00   54
 30  \w     54.00 103.00   0.50    2.32    --  113.00 -94.00  60.00   98
 31  \w     46.00  72.00   0.50    2.32    --  113.00 -61.00  60.00   52
 32  \w     45.00  91.00   0.50    2.32    --  113.00 -94.00  30.00   92
 33  \w     40.00  68.00   0.50    2.32    --  113.00-111.00  90.00   56
 34  \w     44.00  69.00   0.50    2.32    --  113.00 -61.00 150.00   50
 35  \w     43.00  68.00   0.50    2.32    --  113.00 -94.00  90.00   50
 36  \w     33.00 108.00   0.50    2.32    --  113.00-111.00 150.00  150
 37  \w     33.00 108.00   0.50    2.32    --  113.00-111.00  60.00  150
 38  \w     38.00  71.00   0.50    2.32    --  113.00 -61.00 -60.00   66
 39  \w     38.00  70.00   0.50    2.32    --  113.00 -61.00 -90.00   64
 40  \w     44.00  72.00   0.50    2.32    --  113.00 -61.00-150.00   56
 41  \w     52.00  80.00   0.50    2.32    --  113.00 -77.00-180.00   56
 42  \w     37.00  62.00   0.50    2.32    --  113.00-111.00-120.00   50
 43  \w     34.00  70.00   0.50    2.32    --  113.00-111.00-180.00   72
 44  \w     72.00 109.00   0.50    0.58    --   38.95-145.00-169.00   74
 45  \w     18.00  99.00   0.50    0.58    --   38.95-126.00  -1.00  162
 46  \w     36.00 105.00   0.50    2.32    --  113.00-111.00   0.00  138
 47  \w     -9.00  21.00   0.50    0.58    --   38.95 -19.00-120.00   60
 48  \w     84.00 167.00   0.50    2.32    --  113.00  45.00-180.00  166
 49  \w     84.00 177.00   0.50    2.32    --  113.00  45.00 -60.00  186
 50  \w     84.00 140.00   0.50    2.32    --  113.00 178.00   0.00  112
 51  \w     79.00 146.00   0.50    2.32    --  113.00 145.00-116.00  134
 52  \w     50.00 104.00   0.50    2.32    --  113.00 178.00  90.00  108
 53  \w     47.00  72.00   0.50    2.32    --  113.00 178.00   0.00   50
 54  \w    -74.00 -45.00   0.50    0.58    --  -38.95 126.00  75.00   58
 55  \w    -92.00 -67.00   0.50    2.32    -- -102.00 126.00  75.00   50
 56  \w    -64.00 -38.00   0.50    2.32    -- -102.00 136.00  20.52   52
 57  \w   -100.00 -75.00   0.50    0.58    --  -38.95 145.00-116.00   50
 58  \w    -49.00 -24.00   0.50    2.32    -- -102.00  45.00  60.00   50
 59  \w    -48.00 -23.00   0.50    2.32    -- -102.00  45.00  90.00   50
 60  \w    -49.00 -24.00   0.50    2.32    -- -102.00  45.00 -60.00   50
 61  \w    -49.00 -24.00   0.50    2.32    -- -102.00  45.00 -90.00   50
 62  \w    -48.00 -23.00   0.50    2.32    -- -102.00  45.00-150.00   50
 63  \w    -57.00 -31.00   0.50    2.32    -- -102.00 111.00-180.00   52
 64  \w   -100.00 -75.00   0.50    2.32    -- -102.00 145.00-116.00   50
 65  \w   -108.00 -82.00   0.50    2.32    -- -102.00 111.00-180.00   52
 66  \w   -149.00-124.00   0.50    2.32    -- -102.00-126.00  -1.00   50
 67  \w    -88.00 -63.00   0.50    0.58    --  -38.95-145.00-169.00   50
 68  \w   -139.00-114.00   0.50    2.32    -- -102.00-145.00-169.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0580864000
_diffrn_orient_matrix_UB_12      -0.0109747000
_diffrn_orient_matrix_UB_13      0.0653777000
_diffrn_orient_matrix_UB_21      0.1117792000
_diffrn_orient_matrix_UB_22      0.0382903000
_diffrn_orient_matrix_UB_23      0.0497112000
_diffrn_orient_matrix_UB_31      -0.0101443000
_diffrn_orient_matrix_UB_32      0.1010948000
_diffrn_orient_matrix_UB_33      -0.0055984000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            50732
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.500
_diffrn_reflns_theta_min         3.967
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.844
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.37a (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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_description       prism
_exptl_crystal_F_000             1445
_exptl_crystal_recrystallization_method 'recrystallization from chloroform'
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.051
_refine_diff_density_max         2.191
_refine_diff_density_min         -0.711
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1014
_refine_ls_number_reflns         13945
_refine_ls_number_restraints     822
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0656P)^2^+2.0461P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1414
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12727
_reflns_number_total             13945
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00428c2.cif
_cod_data_source_block           kf190708
_cod_database_code               7129705
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         C46H24
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(Cl4C) \\sim Ueq, Uanis(C1C) \\sim Ueq, Uanis(Cl3C) \\sim Ueq, Uanis(Cl2C)
\\sim Ueq, : with sigma of 0.1 and sigma for terminal atoms of 0.2
3. Others
 Fixed Sof: Cl4C(0.25) Cl3C(0.25) Cl2C(0.25) C1C(0.25) H1C(0.25)
4.a Ternary CH refined with riding coordinates:
 C1C(H1C)
4.b Aromatic/amide H refined with riding coordinates:
 C1B(H1B), C51B(H51B), C5B(H5B), C1A(H1A), C5A(H5A), C9B(H9B), C10B(H10B),
 C14B(H14B), C12B(H12B), C34A(H34A), C39B(H39B), C38B(H38B), C36A(H36A),
 C15B(H15B), C47B(H47B), C17B(H17B), C11B(H11B), C9A(H9A), C10A(H10A),
 C17A(H17A), C36B(H36B), C33A(H33A), C18A(H18A), C41B(H41B), C15A(H15A),
 C14A(H14A), C34B(H34B), C42B(H42B), C33B(H33B), C44B(H44B), C31A(H31A),
 C12A(H12A), C28B(H28B), C20A(H20A), C45B(H45B), C46B(H46B), C18B(H18B),
 C31B(H31B), C11A(H11A), C30A(H30A), C28A(H28A), C30B(H30B), C20B(H20B),
 C38A(H38A), C39A(H39A), C42A(H42A), C26A(H26A), C22A(H22A), C26B(H26B),
 C25B(H25B), C41A(H41A), C46A(H46A), C25A(H25A), C23A(H23A), C23B(H23B),
 C22B(H22B), C44A(H44A), C45A(H45A)
;
_olex2_exptl_crystal_mounting_method loop
_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 1.243
_oxdiff_exptl_absorpt_empirical_full_min 0.853