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_7123315
_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         'C42 H36 Br2 N6 O2, 0.5(C6 H5 I)'
_chemical_formula_sum            'C44.98 H38.48 Br2 I0.5 N6 O2'
_chemical_formula_weight         917.63
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-25 deposited with the CCDC.    2019-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.071(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.8680(5)
_cell_length_b                   4.6477(2)
_cell_length_c                   26.6829(9)
_cell_measurement_reflns_used    9941
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.355
_cell_measurement_theta_min      2.607
_cell_volume                     1937.53(12)
_computing_cell_refinement       'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_computing_data_collection       'Bruker APEX3 v2016.5-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT+ Ver. 8.38A (Bruker-AXS, 2016)'
_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      100(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  0.0607
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            37894
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.384
_diffrn_reflns_theta_max         26.384
_diffrn_reflns_theta_min         1.303
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.534
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0969 before and 0.0572 after correction.
The Ratio of minimum to maximum transmission is 0.8998.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_description       needle
_exptl_crystal_F_000             925
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3962
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0320P)^2^+3.9374P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0889
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3372
_reflns_number_total             3962
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01725a2.cif
_cod_data_source_block           brnph3dmc_i
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_formula_sum        'C44.98 H38.48 Br2 I0.50 N6 O2'
_cod_database_code               7123315
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.928
_shelx_estimated_absorpt_t_min   0.606
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 I1S-C1S
 2.1 with sigma of 0.01
 C7S-I2S
 2.1 with sigma of 0.01
 N2-H2 = N1-H1
 0.84 with sigma of 0.02
 C8S-I2S \\sim C12S-I2S
 with sigma of 0.01
 C2S-I1S \\sim C6S-I1S
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(I2S) \\sim Ueq, Uanis(I1S) \\sim Ueq: with sigma of 0.0075 and sigma for
terminal atoms of 0.015
Uanis(C9S) \\sim Ueq, Uanis(C10S) \\sim Ueq, Uanis(C11S) \\sim Ueq, Uanis(C5S)
\\sim Ueq, Uanis(C12S) \\sim Ueq, Uanis(C6S) \\sim Ueq, Uanis(C1S) \\sim Ueq,
Uanis(C7S) \\sim Ueq, Uanis(C2S) \\sim Ueq, Uanis(C8S) \\sim Ueq, Uanis(C3S)
\\sim Ueq, Uanis(C4S) \\sim Ueq: with sigma of 0.015 and sigma for terminal
atoms of 0.02
Uanis(C7S) = Uanis(C8S) = Uanis(C9S) = Uanis(C10S) = Uanis(C11S) = Uanis(C12S)
= Uanis(C1S) = Uanis(C2S) = Uanis(C3S) = Uanis(C4S) = Uanis(C5S) = Uanis(C6S)
4. Others
 Sof(C7S)=Sof(C8S)=Sof(H8S)=Sof(C9S)=Sof(H9S)=Sof(C10S)=Sof(H10S)=Sof(C11S)=
 Sof(H11S)=Sof(C12S)=Sof(H12S)=Sof(I2S)=FVAR(1)
 Sof(C1S)=Sof(C2S)=Sof(H2S)=Sof(C3S)=Sof(H3S)=Sof(C4S)=Sof(H4S)=Sof(C5S)=
 Sof(H5S)=Sof(C6S)=Sof(H6S)=Sof(I1S)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C21(H21A,H21B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17), C19(H19), C20(H20), C8S(H8S), C9S(H9S), C10S(H10S),
 C11S(H11S), C12S(H12S), C2S(H2S), C3S(H3S), C4S(H4S), C5S(H5S), C6S(H6S)
5.c Fitted hexagon refined as free rotating group:
 C7S(C8S,C9S,C10S,C11S,C12S), C1S(C2S,C3S,C4S,C5S,C6S)
;
_shelx_res_checksum              26794
_olex2_submission_special_instructions 'No special instructions were received'