Inclusion crystals as vapochromic chemosensors: fabrication of a mini-sensor array for discrimination of small aromatic molecules based on side-chain engineering of naphthalenediimide derivatives
Ono, Toshikazu; Tsukiyama, Yoshifumi; Hatanaka, Sou; Sakatsume, Yuma; Ogoshi, Tomoki; Hisaeda, Yoshio; Journal of Materials Chemistry C 7 (2019) 9726–; doi:10.1039/C9TC03140E

data_7237918
_publ_section_title
;
 Inclusion crystals as vapochromic chemosensors: fabrication of a
 mini-sensor array for discrimination of small aromatic molecules based on
 side-chain engineering of naphthalenediimide derivatives
;
_journal_issue                   31
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              9726
_journal_paper_doi               10.1039/C9TC03140E
_journal_volume                  7
_journal_year                    2019
_chemical_formula_moiety         '2(C20 H13 N O2), C7 H8'
_chemical_formula_sum            'C47 H34 N2 O4'
_chemical_formula_weight         690.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-22
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_audit_update_record
;
2019-04-26 deposited with the CCDC.	2019-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.56(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.032(4)
_cell_length_b                   5.7620(12)
_cell_length_c                   30.235(7)
_cell_measurement_reflns_used    1033
_cell_measurement_temperature    123
_cell_measurement_theta_max      21.0340
_cell_measurement_theta_min      2.7070
_cell_volume                     3430.8(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32e (Rigaku OD, 2017)'
_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_type            CCD
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -74.00 119.00   1.00  100.00    --   30.00  54.00 120.00  193
  2  \w    -74.00 119.00   1.00  100.00    --   30.00  54.00  30.00  193
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0246460000
_diffrn_orient_matrix_UB_12      0.0317503000
_diffrn_orient_matrix_UB_13      -0.0189859000
_diffrn_orient_matrix_UB_21      0.0261918000
_diffrn_orient_matrix_UB_22      0.0233416000
_diffrn_orient_matrix_UB_23      -0.0122672000
_diffrn_orient_matrix_UB_31      -0.0014175000
_diffrn_orient_matrix_UB_32      -0.1167277000
_diffrn_orient_matrix_UB_33      -0.0076447000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1634
_diffrn_reflns_av_unetI/netI     0.1756
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            22322
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.683
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32e (Rigaku Oxford Diffraction, 2017)
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    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     548
_refine_ls_number_reflns         7001
_refine_ls_number_restraints     264
_refine_ls_restrained_S_all      0.946
_refine_ls_R_factor_all          0.2081
_refine_ls_R_factor_gt           0.0716
_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^)+(0.0310P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1698
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2758
_reflns_number_total             7001
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9tc03140e2.cif
_cod_data_source_block           tsukiyama006
_cod_database_code               7237918
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     isocorrole
_diffrn_oxdiff_ac3_digest_frames
;
01859feff9b55ff59d557fabe1c9e255ba003863a12
;
_diffrn_oxdiff_ac3_digest_hkl
;
017f93b983faac6c332b7b0fc9cd0497d2dd23
;
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C01D \\sim C01D \\sim C01D \\sim C014 \\sim C014 \\sim C014 \\sim C01B \\sim
C01B \\sim C01B \\sim C019 \\sim C019 \\sim C019 \\sim C018 \\sim C018 \\sim
C018 \\sim C018 \\sim C01C \\sim C01C \\sim C01C \\sim C01E \\sim C01E \\sim
C01E \\sim C2 \\sim C2 \\sim C2 \\sim C0AA \\sim C0AA \\sim C0AA \\sim C3 \\sim
C3 \\sim C3 \\sim C0 \\sim C0 \\sim C0 \\sim C0 \\sim C1AA \\sim C1AA \\sim
C1AA \\sim C1 \\sim C1 \\sim C2AA \\sim C2AA: within 1.7A with sigma of 0.04
and sigma for terminal atoms of 0.08
Uanis(C00X) \\sim Ueq, Uanis(C01G) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 C01D, C01D, C01D, C014, C014, C014, C01B, C01B, C01B, C019, C019, C019, C018,
 C018, C018, C018, C01C, C01C, C01C, C01E, C01E, C01E, C2, C2, C2, C0AA, C0AA,
 C0AA, C3, C3, C3, C0, C0, C0, C0, C1AA, C1AA, C1AA, C1, C1, C2AA, C2AA
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(C01E)=Sof(H01J)=Sof(C2)=Sof(H2)=Sof(C0AA)=Sof(H0AA)=Sof(C3)=Sof(H3)=
 Sof(C0)=Sof(C1AA)=Sof(H1AA)=Sof(C2AA)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=1-FVAR(1)
 Sof(C01D)=Sof(H01D)=Sof(C014)=Sof(H014)=Sof(C01B)=Sof(H01C)=Sof(C019)=
 Sof(H019)=Sof(C018)=Sof(C01C)=Sof(H01E)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=
 FVAR(1)
 Sof(H01B)=Sof(C3AA)=Sof(H3AA)=Sof(C01I)=Sof(H01I)=Sof(C4AA)=Sof(H4AA)=1-FVAR(2)
 Sof(H01A)=Sof(C01F)=Sof(H01F)=Sof(C01G)=Sof(H01G)=Sof(C01H)=Sof(H01H)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C00S(H00A,H00B), C00T(H00C,H00D)
5.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00I(H00I), C00K(H00K), C00L(H00L), C00P(H00P), C00Q(H00Q),
 C00U(H00U), C00V(H00V), C00W(H00W), C00Y(H00Y), C00Z(H00Z), C010(H010),
 C011(H011), C012(H012), C013(H013), C015(H015), C016(H016), C017(H017),
 C01A(H01A), C01A(H01B), C01D(H01D), C014(H014), C01B(H01C), C019(H019),
 C01C(H01E), C01F(H01F), C01G(H01G), C01H(H01H), C01E(H01J), C2(H2), C0AA(H0AA),
  C3(H3), C1AA(H1AA), C3AA(H3AA), C01I(H01I), C4AA(H4AA)
5.c Fitted hexagon refined as free rotating group:
 C01D(C014,C01B,C019,C018,C01C), C01E(C2,C0AA,C3,C0,C1AA)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2AA(H2AA,H2AB,H2AC)
;
_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 1.349
_oxdiff_exptl_absorpt_empirical_full_min 0.724