Single-crystal-to-single-crystal guest exchange in columnar assembled brominated triphenylamine bis-urea macrocycles
Sindt, Ammon J.; Smith, Mark D.; Berens, Samuel; Vasenkov, Sergey; Bowers, Clifford; Shimizu, Linda S.; Chemical Communications  (2019) –; doi:10.1039/C9CC01725A

data_7123313
_publ_section_title
;
 Single-crystal-to-single-crystal guest exchange in columnar assembled
 brominated triphenylamine bis-urea macrocycles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01725A
_journal_year                    2019
_chemical_formula_moiety         'C54 H58 Br2 N8 O2, 8(C1 H1 Cl3)'
_chemical_formula_sum            'C62 H66 Br2 Cl24 N8 O2'
_chemical_formula_weight         1965.84
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-02-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-02-25 deposited with the CCDC.    2019-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                91.288(2)
_cell_angle_beta                 105.248(2)
_cell_angle_gamma                95.864(2)
_cell_formula_units_Z            1
_cell_length_a                   12.3182(5)
_cell_length_b                   12.4639(5)
_cell_length_c                   14.2206(5)
_cell_measurement_reflns_used    9408
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.71
_cell_measurement_theta_min      2.25
_cell_volume                     2092.67(14)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'Bruker PHOTON-100 area detector'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            66320
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         2.159
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.780
_exptl_absorpt_correction_T_max  0.6027
_exptl_absorpt_correction_T_min  0.4947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0881 before and 0.0460 after correction.
The Ratio of minimum to maximum transmission is 0.8208.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_description       block
_exptl_crystal_F_000             988
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.949
_refine_diff_density_min         -1.087
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     634
_refine_ls_number_reflns         7388
_refine_ls_number_restraints     146
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0624
_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^)+(0.0962P)^2^+3.9955P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1705
_refine_ls_wR_factor_ref         0.1859
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5844
_reflns_number_total             7388
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01725a2.cif
_cod_data_source_block           brnph3pmc
_cod_database_code               7123313
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.675
_shelx_estimated_absorpt_t_min   0.482
_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
 Cl4-C32 = Cl1-C31 = Cl3-C31 = Cl6-C32 = Cl5-C32 = Cl2-C31
 1.75 with sigma of 0.02
 Cl11-C34 = Cl12-C34 = Cl8-C33 = Cl9-C33 = Cl10-C34 = Cl7-C33 = C41-Cl31 = C41-
 Cl32 = C41-Cl33
 1.75 with sigma of 0.02
 Cl17-C36 = Cl14-C35 = Cl15-C35 = Cl18-C36 = Cl13-C35 = Cl16-C36
 1.75 with sigma of 0.02
 Cl26-C39 = Cl22-C38 = Cl25-C39 = Cl23-C38 = Cl21-C37 = Cl19-C37 = Cl27-C39 =
 Cl20-C37 = Cl24-C38 = Cl28-C40 = Cl29-C40 = Cl30-C40
 1.75 with sigma of 0.02
 Cl19-Cl20 \\sim Cl20-Cl21 \\sim Cl21-Cl19 \\sim Cl22-Cl23 \\sim Cl23-Cl24
\\sim Cl24-Cl22 \\sim Cl25-
 Cl26 \\sim Cl26-Cl27 \\sim Cl27-Cl25 \\sim Cl28-Cl29 \\sim Cl29-Cl30 \\sim
Cl30-Cl28 \\sim Cl31-Cl32 \\ Cl32-Cl33 \\sim Cl33-Cl31
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C37) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C31) = Uanis(C32)
Uanis(Cl5) = Uanis(Cl2)
Uanis(Cl1) = Uanis(Cl4)
Uanis(C33) = Uanis(C34) = Uanis(C41)
Uanis(C35) = Uanis(C36)
Uanis(C38) = Uanis(C39) = Uanis(C40)
Uanis(Cl24) = Uanis(Cl29)
Uanis(Cl11) = Uanis(Cl32)
Uanis(Cl33) = Uanis(Cl9)
Uanis(Cl30) = Uanis(Cl23)
4. Others
 1*[Sof(Cl19)+Sof(Cl20)+Sof(Cl21)+Sof(C37)+Sof(H37)]+1*[Sof(Cl22)+Sof(Cl23)+
 Sof(Cl24)+Sof(C38)+Sof(H38)]+1*[Sof(Cl25)+Sof(Cl26)+Sof(Cl27)+Sof(C39)+
 Sof(H39)]+1*[Sof(Cl28)+Sof(Cl29)+Sof(Cl30)+Sof(C40)+Sof(H40)]=1 with esd of
 0.00001
 1*[Sof(Cl7)+Sof(Cl8)+Sof(Cl9)+Sof(C33)+Sof(H33)]+1*[Sof(Cl10)+Sof(Cl11)+
 Sof(Cl12)+Sof(C34)+Sof(H34)]+1*[Sof(Cl31)+Sof(Cl32)+Sof(Cl33)+Sof(C41)+
 Sof(H41)]=1 with esd of 0.00001
 Sof(Cl4)=Sof(Cl5)=Sof(Cl6)=Sof(C32)=Sof(H32)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=Sof(C31)=Sof(H31)=FVAR(1)
 Sof(Cl7)=Sof(Cl8)=Sof(Cl9)=Sof(C33)=Sof(H33)=FVAR(2)
 Sof(Cl16)=Sof(Cl17)=Sof(Cl18)=Sof(C36)=Sof(H36)=1-FVAR(3)
 Sof(Cl13)=Sof(Cl14)=Sof(Cl15)=Sof(C35)=Sof(H35)=FVAR(3)
 Sof(Cl19)=Sof(Cl20)=Sof(Cl21)=Sof(C37)=Sof(H37)=FVAR(4)
 Sof(Cl22)=Sof(Cl23)=Sof(Cl24)=Sof(C38)=Sof(H38)=FVAR(5)
 Sof(Cl25)=Sof(Cl26)=Sof(Cl27)=Sof(C39)=Sof(H39)=FVAR(6)
 Sof(Cl28)=Sof(Cl29)=Sof(Cl30)=Sof(C40)=Sof(H40)=FVAR(7)
 Sof(Cl10)=Sof(Cl11)=Sof(Cl12)=Sof(C34)=Sof(H34)=FVAR(8)
 Sof(Cl31)=Sof(Cl32)=Sof(Cl33)=Sof(C41)=Sof(H41)=FVAR(9)
5.a Ternary CH refined with riding coordinates:
 C31(H31), C32(H32), C33(H33), C34(H34), C41(H41), C35(H35), C36(H36),
 C37(H37), C38(H38), C39(H39), C40(H40)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C23(H23A,H23B)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16),
 C18(H18), C19(H19), C21(H21), C22(H22)
5.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              23462
_olex2_submission_special_instructions 'No special instructions were received'