#------------------------------------------------------------------------------
#$Date: 2019-04-19 01:06:23 +0300 (Fri, 19 Apr 2019) $
#$Revision: 214691 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/33/7123316.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7123316
loop_
_publ_author_name
'Sindt, Ammon J.'
'Smith, Mark D.'
'Berens, Samuel'
'Vasenkov, Sergey'
'Bowers, Clifford'
'Shimizu, Linda S.'
_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'
_chemical_formula_sum            'C42 H36 Br2 N6 O2'
_chemical_formula_weight         816.59
_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             2019-01-18
_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                 100.316(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.8204(7)
_cell_length_b                   4.6117(2)
_cell_length_c                   26.8694(12)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.561
_cell_measurement_theta_min      2.617
_cell_volume                     1928.67(15)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω and φ 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  0.0610
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            28652
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        27.589
_diffrn_reflns_theta_max         27.589
_diffrn_reflns_theta_min         2.617
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.145
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1468 before and 0.0588 after correction.
The Ratio of minimum to maximum transmission is 0.8644.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         4436
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0310
_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/[σ²(Fo²)+(0.0328P)²+1.5049P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0775
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3673
_reflns_number_total             4436
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc01725a2.cif
_cod_data_source_block           brnph3dmc_mt2
_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_database_code               7123316
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.481
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N1-H1 = N2-H2
 0.85 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uiso(H2) = Uiso(H1)
4.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C21(H21A,H21B)
4.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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
Br1 Br 1.17486(2) 0.85851(6) 0.72133(2) 0.02505(8) Uani 1 1 d .
O1 O 0.60222(9) 0.8962(3) 0.33679(6) 0.0208(3) Uani 1 1 d .
N1 N 0.53413(10) 0.4647(4) 0.31816(7) 0.0173(4) Uani 1 1 d D
H1 H 0.5400(14) 0.288(4) 0.3208(9) 0.014(4) Uiso 1 1 d D
N2 N 0.67420(10) 0.4749(4) 0.35709(6) 0.0153(3) Uani 1 1 d D
H2 H 0.6721(14) 0.299(4) 0.3562(9) 0.014(4) Uiso 1 1 d D
N3 N 0.82046(11) 0.6614(4) 0.59475(6) 0.0209(4) Uani 1 1 d .
C1 C 0.60322(12) 0.6277(4) 0.33745(7) 0.0131(4) Uani 1 1 d .
C2 C 0.75533(12) 0.6118(5) 0.37780(7) 0.0161(4) Uani 1 1 d .
H2A H 0.755518 0.810785 0.364016 0.019 Uiso 1 1 calc R
H2B H 0.802283 0.502547 0.366431 0.019 Uiso 1 1 calc R
C3 C 0.77336(12) 0.6277(4) 0.43479(7) 0.0149(4) Uani 1 1 d .
C4 C 0.84951(12) 0.5221(5) 0.46262(8) 0.0175(4) Uani 1 1 d .
H4 H 0.891283 0.440350 0.445404 0.021 Uiso 1 1 calc R
C5 C 0.86597(13) 0.5334(5) 0.51515(8) 0.0190(4) Uani 1 1 d .
H5 H 0.918366 0.458289 0.533422 0.023 Uiso 1 1 calc R
C6 C 0.80583(13) 0.6546(5) 0.54106(7) 0.0180(4) Uani 1 1 d .
C7 C 0.73003(13) 0.7657(5) 0.51333(8) 0.0203(4) Uani 1 1 d .
H7 H 0.688915 0.852435 0.530467 0.024 Uiso 1 1 calc R
C8 C 0.71395(13) 0.7512(5) 0.46119(8) 0.0186(4) Uani 1 1 d .
H8 H 0.661569 0.826619 0.442948 0.022 Uiso 1 1 calc R
C9 C 0.90431(12) 0.6978(5) 0.62284(8) 0.0170(4) Uani 1 1 d .
C10 C 0.96166(14) 0.8906(5) 0.60665(8) 0.0212(4) Uani 1 1 d .
H10 H 0.944905 0.992977 0.575777 0.025 Uiso 1 1 calc R
C11 C 1.04284(14) 0.9346(5) 0.63506(8) 0.0218(5) Uani 1 1 d .
H11 H 1.081647 1.066086 0.623801 0.026 Uiso 1 1 calc R
C12 C 1.06660(12) 0.7852(5) 0.67991(8) 0.0180(4) Uani 1 1 d .
C13 C 1.01187(13) 0.5870(5) 0.69615(8) 0.0191(4) Uani 1 1 d .
H13 H 1.029395 0.482244 0.726698 0.023 Uiso 1 1 calc R
C14 C 0.93102(13) 0.5431(5) 0.66725(8) 0.0188(4) Uani 1 1 d .
H14 H 0.893380 0.405347 0.677970 0.023 Uiso 1 1 calc R
C15 C 0.75125(12) 0.6077(5) 0.62102(8) 0.0174(4) Uani 1 1 d .
C16 C 0.74653(12) 0.7555(5) 0.66536(8) 0.0176(4) Uani 1 1 d .
H16 H 0.787986 0.899765 0.677495 0.021 Uiso 1 1 calc R
C17 C 0.68110(12) 0.6929(5) 0.69212(8) 0.0174(4) Uani 1 1 d .
H17 H 0.679249 0.792064 0.722893 0.021 Uiso 1 1 calc R
C18 C 0.61858(12) 0.4882(5) 0.67463(7) 0.0156(4) Uani 1 1 d .
C19 C 0.62223(14) 0.3496(5) 0.62921(8) 0.0220(4) Uani 1 1 d .
H19 H 0.578816 0.213729 0.616016 0.026 Uiso 1 1 calc R
C20 C 0.68800(14) 0.4056(5) 0.60278(8) 0.0227(5) Uani 1 1 d .
H20 H 0.689918 0.305634 0.572086 0.027 Uiso 1 1 calc R
C21 C 0.54885(12) 0.4163(5) 0.70429(8) 0.0181(4) Uani 1 1 d .
H21A H 0.543864 0.202924 0.706589 0.022 Uiso 1 1 calc R
H21B H 0.565454 0.492689 0.739105 0.022 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 H1 116.5(16) . .
C1 N1 C21 123.98(18) . 3_666
C21 N1 H1 119.4(16) 3_666 .
C1 N2 H2 118.9(16) . .
C1 N2 C2 122.70(18) . .
C2 N2 H2 118.3(16) . .
C6 N3 C15 119.95(16) . .
C9 N3 C6 120.76(16) . .
C9 N3 C15 119.10(16) . .
O1 C1 N1 122.90(18) . .
O1 C1 N2 122.33(18) . .
N2 C1 N1 114.76(18) . .
N2 C2 H2A 108.8 . .
N2 C2 H2B 108.8 . .
N2 C2 C3 113.86(16) . .
H2A C2 H2B 107.7 . .
C3 C2 H2A 108.8 . .
C3 C2 H2B 108.8 . .
C4 C3 C2 121.23(17) . .
C4 C3 C8 117.88(18) . .
C8 C3 C2 120.89(17) . .
C3 C4 H4 119.3 . .
C3 C4 C5 121.41(19) . .
C5 C4 H4 119.3 . .
C4 C5 H5 119.9 . .
C4 C5 C6 120.15(19) . .
C6 C5 H5 119.9 . .
C5 C6 N3 121.00(18) . .
C7 C6 N3 120.27(18) . .
C7 C6 C5 118.72(19) . .
C6 C7 H7 119.7 . .
C8 C7 C6 120.69(19) . .
C8 C7 H7 119.7 . .
C3 C8 H8 119.4 . .
C7 C8 C3 121.13(19) . .
C7 C8 H8 119.4 . .
C10 C9 N3 120.66(19) . .
C14 C9 N3 120.61(19) . .
C14 C9 C10 118.72(19) . .
C9 C10 H10 119.6 . .
C11 C10 C9 120.8(2) . .
C11 C10 H10 119.6 . .
C10 C11 H11 120.4 . .
C12 C11 C10 119.2(2) . .
C12 C11 H11 120.4 . .
C11 C12 Br1 119.92(16) . .
C11 C12 C13 121.17(19) . .
C13 C12 Br1 118.89(16) . .
C12 C13 H13 120.4 . .
C12 C13 C14 119.12(19) . .
C14 C13 H13 120.4 . .
C9 C14 H14 119.5 . .
C13 C14 C9 120.9(2) . .
C13 C14 H14 119.5 . .
C16 C15 N3 120.28(18) . .
C16 C15 C20 119.10(19) . .
C20 C15 N3 120.62(19) . .
C15 C16 H16 120.0 . .
C15 C16 C17 120.09(19) . .
C17 C16 H16 120.0 . .
C16 C17 H17 119.4 . .
C18 C17 C16 121.15(19) . .
C18 C17 H17 119.4 . .
C17 C18 C19 118.16(19) . .
C17 C18 C21 121.01(18) . .
C19 C18 C21 120.82(19) . .
C18 C19 H19 119.4 . .
C20 C19 C18 121.2(2) . .
C20 C19 H19 119.4 . .
C15 C20 H20 119.9 . .
C19 C20 C15 120.2(2) . .
C19 C20 H20 119.9 . .
N1 C21 C18 112.95(17) 3_666 .
N1 C21 H21A 109.0 3_666 .
N1 C21 H21B 109.0 3_666 .
C18 C21 H21A 109.0 . .
C18 C21 H21B 109.0 . .
H21A C21 H21B 107.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C12 1.898(2) .
O1 C1 1.239(2) .
N1 H1 0.820(16) .
N1 C1 1.351(3) .
N1 C21 1.451(2) 3_666
N2 H2 0.810(16) .
N2 C1 1.350(2) .
N2 C2 1.449(2) .
N3 C6 1.420(3) .
N3 C9 1.414(3) .
N3 C15 1.427(3) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C2 C3 1.508(3) .
C3 C4 1.387(3) .
C3 C8 1.397(3) .
C4 H4 0.9500 .
C4 C5 1.389(3) .
C5 H5 0.9500 .
C5 C6 1.393(3) .
C6 C7 1.391(3) .
C7 H7 0.9500 .
C7 C8 1.380(3) .
C8 H8 0.9500 .
C9 C10 1.394(3) .
C9 C14 1.390(3) .
C10 H10 0.9500 .
C10 C11 1.386(3) .
C11 H11 0.9500 .
C11 C12 1.381(3) .
C12 C13 1.382(3) .
C13 H13 0.9500 .
C13 C14 1.387(3) .
C14 H14 0.9500 .
C15 C16 1.386(3) .
C15 C20 1.391(3) .
C16 H16 0.9500 .
C16 C17 1.392(3) .
C17 H17 0.9500 .
C17 C18 1.387(3) .
C18 C19 1.388(3) .
C18 C21 1.509(3) .
C19 H19 0.9500 .
C19 C20 1.385(3) .
C20 H20 0.9500 .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O1 0.820(16) 2.067(17) 2.845(2) 158(2) 1_545 yes
N2 H2 O1 0.810(16) 2.179(18) 2.915(2) 151(2) 1_545 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
Br1 C12 C13 C14 176.86(16) . .
N2 C2 C3 C4 126.8(2) . .
N2 C2 C3 C8 -53.6(3) . .
N3 C6 C7 C8 -177.8(2) . .
N3 C9 C10 C11 177.6(2) . .
N3 C9 C14 C13 -177.17(19) . .
N3 C15 C16 C17 -177.04(19) . .
N3 C15 C20 C19 178.4(2) . .
C1 N2 C2 C3 100.9(2) . .
C2 N2 C1 O1 -1.6(3) . .
C2 N2 C1 N1 177.67(17) . .
C2 C3 C4 C5 -179.3(2) . .
C2 C3 C8 C7 179.8(2) . .
C3 C4 C5 C6 -0.5(3) . .
C4 C3 C8 C7 -0.6(3) . .
C4 C5 C6 N3 178.3(2) . .
C4 C5 C6 C7 -0.7(3) . .
C5 C6 C7 C8 1.2(3) . .
C6 N3 C9 C10 39.9(3) . .
C6 N3 C9 C14 -140.4(2) . .
C6 N3 C15 C16 -144.4(2) . .
C6 N3 C15 C20 36.0(3) . .
C6 C7 C8 C3 -0.6(3) . .
C8 C3 C4 C5 1.1(3) . .
C9 N3 C6 C5 34.3(3) . .
C9 N3 C6 C7 -146.7(2) . .
C9 N3 C15 C16 40.7(3) . .
C9 N3 C15 C20 -139.0(2) . .
C9 C10 C11 C12 -0.1(3) . .
C10 C9 C14 C13 2.5(3) . .
C10 C11 C12 Br1 -176.40(16) . .
C10 C11 C12 C13 1.9(3) . .
C11 C12 C13 C14 -1.4(3) . .
C12 C13 C14 C9 -0.8(3) . .
C14 C9 C10 C11 -2.1(3) . .
C15 N3 C6 C5 -140.6(2) . .
C15 N3 C6 C7 38.4(3) . .
C15 N3 C9 C10 -145.2(2) . .
C15 N3 C9 C14 34.5(3) . .
C15 C16 C17 C18 -1.5(3) . .
C16 C15 C20 C19 -1.2(3) . .
C16 C17 C18 C19 -0.9(3) . .
C16 C17 C18 C21 178.68(19) . .
C17 C18 C19 C20 2.2(3) . .
C17 C18 C21 N1 106.2(2) . 3_666
C18 C19 C20 C15 -1.2(3) . .
C19 C18 C21 N1 -74.3(3) . 3_666
C20 C15 C16 C17 2.6(3) . .
C21 N1 C1 O1 -1.4(3) 3_666 .
C21 N1 C1 N2 179.33(18) 3_666 .
C21 C18 C19 C20 -177.3(2) . .
