Synthesis and size-dependent properties of multiple sizes of chlorinated fluorocycloparaphenylenes.
Imoto, Daiki; Shudo, Hiroki; Mizukami, Kiichi; Kimizuka, Nobuo; Yagi, Akiko; Itami, Kenichiro; Chemical communications (Cambridge, England) 60 (2024) 12585–12588; doi:10.1039/d4cc03336a

data_7133924
_publ_section_title
;
 Synthesis and size-dependent properties of multiple sizes of chlorinated
 fluorocycloparaphenylenes.
;
_journal_issue                   86
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12585
_journal_page_last               12588
_journal_paper_doi               10.1039/d4cc03336a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C48 H16 Cl8 F8, 2(C6 H12), C4 H8 O'
_chemical_formula_sum            'C64 H48 Cl8 F8 O'
_chemical_formula_weight         1268.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-06-25
_audit_creation_method
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-06-26 deposited with the CCDC.	2024-10-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.005(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.3396(14)
_cell_length_b                   12.3007(12)
_cell_length_c                   28.775(2)
_cell_measurement_reflns_used    4415
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.8990
_cell_measurement_theta_min      2.2610
_cell_volume                     6099.7(9)
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.829
_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     -1.00  26.00   0.50   10.00    --    0.14 -99.00  90.00   54
  2  \w    -12.00  16.00   0.50   10.00    --    0.14  57.00 150.00   56
  3  \w    -15.00  75.00   0.50   10.00    --    0.14  37.00 -90.00  180
  4  \w    -16.00  13.00   0.50   10.00    --    0.14  57.00   0.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            17400
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.824
_diffrn_reflns_theta_min         2.034
_exptl_absorpt_coefficient_mu    0.435
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent dark colourless'
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       block
_exptl_crystal_F_000             2592
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         6601
_refine_ls_number_restraints     202
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0611
_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^)+(0.0667P)^2^+17.6560P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1582
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4985
_reflns_number_total             6601
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03336a2.cif
_cod_data_source_block           imo197d_fcl8cpp_5_8ppm_auto
_cod_original_cell_volume        6099.8(9)
_cod_database_code               7133924
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.938
_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
 C19-C16 = C1A-C19 = C1B-C1A
 1.54 with sigma of 0.01
 O2-C16 = O2-C1B
 1.43 with sigma of 0.01
 C16-C1A
 2.4 with sigma of 0.01
 C19-C1B
 2.4 with sigma of 0.01
 C1A-O2
 2.4 with sigma of 0.01
 C1B-C16
 2.4 with sigma of 0.01
 O2-C19
 2.4 with sigma of 0.01
 C34-C36
 2.4 with sigma of 0.01
 C35-C37
 2.4 with sigma of 0.01
 C37-C35A
 2.4 with sigma of 0.01
 C36A-C34
 2.4 with sigma of 0.01
 C34-C33 = C35-C34 = C35A-C34 = C36-C35 = C36A-C35A = C37-C36A = C37-C36 = C38-
 C37
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C16 \\sim O2 \\sim C1B \\sim C19 \\sim C1A: within 1.7A with sigma of 0.03 and
sigma for terminal atoms of 0.06 within 1.7A
C36 \\sim C37 \\sim C38 \\sim C36A \\sim C35 \\sim C35A \\sim C34 \\sim C33:
within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
Uanis(C19) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C1B)
\\sim Ueq, Uanis(C1A) \\sim Ueq: with sigma of 0.03 and sigma for terminal
atoms of 0.06
Uanis(C35) \\sim Ueq, Uanis(C36A) \\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C38)
\\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C35A) \\sim Ueq, Uanis(C34) \\sim Ueq,
Uanis(C33) \\sim Ueq: with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Others
 Sof(H37A)=Sof(H37B)=Sof(C35A)=Sof(H35C)=Sof(H35D)=Sof(C36A)=Sof(H36C)=
 Sof(H36D)=1-FVAR(1)
 Sof(H34A)=Sof(H34B)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(C36)=Sof(H36A)=Sof(H36B)=
 FVAR(1)
 Fixed Sof: O2(0.5) C16(0.5) H16A(0.5) H16B(0.5) C19(0.5) H19A(0.5) H19B(0.5)
 C1A(0.5) H1AA(0.5) H1AB(0.5) C1B(0.5) H1BA(0.5) H1BB(0.5)
5.a Free rotating group:
 O2(C16,C19,C1A,C1B)
5.b Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B), C16(H16A,
 H16B), C19(H19A,H19B), C1A(H1AA,H1AB), C1B(H1BA,H1BB), C35A(H35C,H35D),
 C36A(H36C,H36D)
5.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C24(H24), C11(H11), C2(H2), C12(H12), C18(H18), C20(H20), C3(H3)
5.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              68864
_shelx_hkl_checksum              44878
_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
;