Macrocycle-based charge transfer co-crystals with specific selective vapochromism to benzene
Zeng, Fei; Tang, Lin-Li; Bao, Wen-Hu; New Journal of Chemistry 48 (2024) 14480–14485; doi:10.1039/D4NJ02859G

data_7063360
_publ_section_title
;
 Macrocycle-based charge transfer co-crystals with specific selective
 vapochromism to benzene
;
_journal_issue                   32
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14480
_journal_page_last               14485
_journal_paper_doi               10.1039/D4NJ02859G
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C66 H60 O12, 2(C10 H2 N4), 3(C H Cl3)'
_chemical_formula_sum            'C89 H67 Cl9 N8 O12'
_chemical_formula_weight         1759.55
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-06-05
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-06-19 deposited with the CCDC.	2024-07-22 downloaded from the CCDC.
;
_cell_angle_alpha                70.993(6)
_cell_angle_beta                 70.564(6)
_cell_angle_gamma                72.967(6)
_cell_formula_units_Z            1
_cell_length_a                   13.062(6)
_cell_length_b                   13.259(6)
_cell_length_c                   13.970(6)
_cell_measurement_reflns_used    1382
_cell_measurement_temperature    296.15(10)
_cell_measurement_theta_max      21.073
_cell_measurement_theta_min      2.580
_cell_volume                     2110.5(16)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker D8 Venture diffractometer'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15(10)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_av_unetI/netI     0.1264
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20443
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.598
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.366
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0540 before and 0.0460 after correction.
The Ratio of minimum to maximum transmission is 0.9119.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       block
_exptl_crystal_F_000             906
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     694
_refine_ls_number_reflns         7439
_refine_ls_number_restraints     401
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.2047
_refine_ls_R_factor_gt           0.0820
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1402P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2156
_refine_ls_wR_factor_ref         0.2927
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2781
_reflns_number_total             7439
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj02859g2.cif
_cod_data_source_block           1a_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7063359--7063362.cif.'
_cod_original_cell_volume        2110.4(16)
_cod_database_code               7063360
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.947
_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. Restrained distances
 Cl2-C44 = Cl1-C44 = Cl3-C44 = Cl5-C45 = Cl4A-C45A = Cl4-C45 = Cl6-C45 = Cl6A-
 C45A = Cl5A-C45A
 1.79 with sigma of 0.01
 Cl2A-C44A = Cl3A-C44A = Cl1A-C44A
 1.79 with sigma of 0.01
 Cl1-Cl2 = Cl1-Cl3 = Cl2-Cl3
 2.924 with sigma of 0.02
 Cl1A-Cl2A = Cl1A-Cl3A = Cl2A-Cl3A
 2.924 with sigma of 0.02
 Cl4A-Cl5A = Cl4A-Cl6A = Cl5A-Cl6A
 2.924 with sigma of 0.02
 Cl4-Cl5 = Cl4-Cl6 = Cl5-Cl6
 2.924 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C44A \\sim Cl1A \\sim Cl2A \\sim Cl3A \\sim C44 \\sim Cl1 \\sim Cl2 \\sim Cl3:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C45 \\sim Cl4 \\sim Cl5 \\sim Cl6 \\sim C45A \\sim Cl4A \\sim Cl5A \\sim Cl6A:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C39 \\sim C40 \\sim N3 \\sim C41 \\sim C42 \\sim C43 \\sim N4 \\sim C39A \\sim
C40A \\sim N3A \\sim C41A \\sim C42A \\sim C43A \\sim N4A: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Same fragment restrains
{C39A, C40A, C41A, C42A, C43A, N3A, N4A} sigma for 1-2: 0.01, 1-3: 0.02
as in
{C39, C40, C41, C42, C43, N3, N4}
5. Others
 Sof(C45A)=Sof(H45A)=Sof(Cl4A)=Sof(Cl5A)=Sof(Cl6A)=1-FVAR(1)
 Sof(C45)=Sof(H45)=Sof(Cl4)=Sof(Cl5)=Sof(Cl6)=FVAR(1)
 Sof(C44A)=Sof(H44A)=Sof(Cl1A)=Sof(Cl2A)=Sof(Cl3A)=0.5*(1-FVAR(3))
 Sof(C44)=Sof(H44)=Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=0.5*FVAR(3)
 Sof(C39A)=Sof(C40A)=Sof(C41A)=Sof(H41A)=Sof(C42A)=Sof(C43A)=Sof(N3A)=Sof(N4A)=
 1-FVAR(3)
 Sof(C39)=Sof(C40)=Sof(C41)=Sof(H41)=Sof(C42)=Sof(C43)=Sof(N3)=Sof(N4)=FVAR(3)
6.a Ternary CH refined with riding coordinates:
 C45(H45), C45A(H45A), C44A(H44A), C44(H44)
6.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B)
6.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C10(H10), C12(H12), C13(H13), C19(H19), C22(H22),
 C27(H27), C30(H30), C36(H36), C41(H41), C41A(H41A)
6.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              62981
_shelx_hkl_checksum              58827
_olex2_submission_special_instructions 'No special instructions were received'