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_7063362
_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         '3(C H2 Br2), 2(C66 H60 O12), 3(C10 H2 N4)'
_chemical_formula_sum            'C165 H132 Br6 N12 O24'
_chemical_formula_weight         3146.28
_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
_audit_creation_date             2024-05-07
_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                86.210(3)
_cell_angle_beta                 88.225(3)
_cell_angle_gamma                64.678(3)
_cell_formula_units_Z            1
_cell_length_a                   12.903(3)
_cell_length_b                   13.152(3)
_cell_length_c                   23.932(6)
_cell_measurement_reflns_used    2976
_cell_measurement_temperature    296.15(10)
_cell_measurement_theta_max      19.497
_cell_measurement_theta_min      2.438
_cell_volume                     3663.0(15)
_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 2014/4 (Sheldrick, 2014)'
_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  0.0737
_diffrn_reflns_av_unetI/netI     0.1096
_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       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            34619
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.749
_diffrn_reflns_theta_max         24.749
_diffrn_reflns_theta_min         1.706
_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    1.720
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0725 before and 0.0444 after correction.
The Ratio of minimum to maximum transmission is 0.8235.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_description       block
_exptl_crystal_F_000             1608
_exptl_crystal_recrystallization_method
'The crystals were growth by means of evaporation of a mixture of n-hexane and toluene at RT.'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1025
_refine_ls_number_reflns         12528
_refine_ls_number_restraints     142
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1947
_refine_ls_R_factor_gt           0.0712
_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^)+(0.1025P)^2^+1.3468P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1736
_refine_ls_wR_factor_ref         0.2360
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4969
_reflns_number_total             12528
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj02859g2.cif
_cod_data_source_block           11_a_a
_cod_depositor_comments
'Adding full bibliography for 7063359--7063362.cif.'
_cod_database_code               7063362
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.820
_shelx_estimated_absorpt_t_min   0.782
_exptl_crystal_mounting_method
'Crystals were removed from the crystallisation vial and immediately coated with polybutenes oil (CAS: 9003-29-6) on a glass slide. A suitable single crystal coated with polybutenes oil as less as possible was sealed in capillary tube filled with argon. The capillary tube with single crystal was mounted on copper pin with solid paraffin.'
_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
 Br3-C82 = C82-Br4
 1.85 with sigma of 0.01
 Br3-Br4
 3.022 with sigma of 0.02
 O11-C65 \\sim O11-C65A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Br1 \\sim Br2 \\sim C02T \\sim Br2A \\sim C02U \\sim Br1A: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
O11 \\sim C65 \\sim C65A: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
Br3 \\sim C82 \\sim Br4 \\sim C82A \\sim Br3A \\sim Br4A: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Same fragment restrains
{Br2A, C02U, Br1A} sigma for 1-2: 0.02, 1-3: 0.02
as in
{Br2, C02T, Br1}
{Br4A, C82A, Br3A} sigma for 1-2: 0.02, 1-3: 0.02
as in
{Br4, C82, Br3}
5. Others
 Sof(Br2A)=Sof(C02U)=Sof(H02C)=Sof(H02D)=Sof(Br1A)=1-FVAR(1)
 Sof(Br2)=Sof(C02T)=Sof(H02A)=Sof(H02B)=Sof(Br1)=FVAR(1)
 Sof(C65A)=Sof(H65D)=Sof(H65E)=Sof(H65F)=1-FVAR(2)
 Sof(C65)=Sof(H65A)=Sof(H65B)=Sof(H65C)=FVAR(2)
 Sof(Br4A)=Sof(C82A)=Sof(H82C)=Sof(H82D)=Sof(Br3A)=0.5*(1-FVAR(4))
 Sof(Br4)=Sof(C82)=Sof(H82A)=Sof(H82B)=Sof(Br3)=0.5*FVAR(4)
6.a Secondary CH2 refined with riding coordinates:
 C02T(H02A,H02B), C82(H82A,H82B), C58(H58A,H58B), C25(H25A,H25B), C02U(H02C,
 H02D), C82A(H82C,H82D)
6.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C47(H47), C44(H44), C7(H7), C12(H12), C22(H22), C55(H55), C6(H6),
 C35(H35), C52(H52), C36(H36), C15(H15), C64(H64), C19(H19), C28(H28), C69(H69),
  C31(H31), C14(H14), C61(H61), C41(H41), C42(H42), C78(H78), C74(H74)
6.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C57(H57A,H57B,H57C), C56(H56A,H56B,H56C), C33(H33A,H33B,
 H33C), C48(H48A,H48B,H48C), C24(H24A,H24B,H24C), C66(H66A,H66B,H66C), C2(H2A,
 H2B,H2C), C49(H49A,H49B,H49C), C1(H1A,H1B,H1C), C32(H32A,H32B,H32C), C65(H65A,
 H65B,H65C), C65A(H65D,H65E,H65F)
;
_shelx_res_checksum              45352
_shelx_hkl_checksum              52108
_olex2_submission_special_instructions 'No special instructions were received'