#------------------------------------------------------------------------------
#$Date: 2019-04-19 01:06:23 +0300 (Fri, 19 Apr 2019) $
#$Revision: 214691 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/33/7123313.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_7123313
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         '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       '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  0.0348
_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 λ/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/[σ²(Fo²)+(0.0962P)²+3.9955P] where P=(Fo²+2Fc²)/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 > 2σ(I)'
_cod_data_source_file            c9cc01725a2.cif
_cod_data_source_block           brnph3pmc
_cod_database_code               7123313
_shelx_shelxl_version_number     2018/1
_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   0.675
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.09339(5) 0.13596(4) 1.15419(4) 0.0708(2) Uani 1 1 d . . . . .
O1 O 0.2141(2) 0.1660(2) 0.4472(2) 0.0456(7) Uani 1 1 d . . . . .
N1 N 0.1306(2) 0.3156(2) 0.4703(2) 0.0328(7) Uani 1 1 d . . . . .
N2 N 0.2496(2) 0.2440(2) 0.6007(2) 0.0371(7) Uani 1 1 d . . . . .
N3 N 0.1980(2) 0.4231(2) 0.6234(2) 0.0336(7) Uani 1 1 d . . . . .
N4 N 0.7713(3) 0.3397(3) 0.8256(2) 0.0433(8) Uani 1 1 d . . . . .
C1 C 0.1984(3) 0.2368(3) 0.5033(3) 0.0341(8) Uani 1 1 d . . . . .
C2 C 0.1098(3) 0.4007(3) 0.5342(3) 0.0347(8) Uani 1 1 d . . . . .
H2A H 0.101258 0.467769 0.498264 0.042 Uiso 1 1 calc R . . . .
H2B H 0.037462 0.378980 0.550319 0.042 Uiso 1 1 calc R . . . .
C3 C 0.2197(3) 0.3214(3) 0.6659(3) 0.0400(9) Uani 1 1 d . . . . .
H3A H 0.151406 0.289763 0.684014 0.048 Uiso 1 1 calc R . . . .
H3B H 0.282246 0.334026 0.726390 0.048 Uiso 1 1 calc R . . . .
C4 C 0.3152(3) 0.1589(3) 0.6469(4) 0.0485(11) Uani 1 1 d . . . . .
H4A H 0.313486 0.101494 0.597080 0.058 Uiso 1 1 calc R . . . .
H4B H 0.280420 0.126345 0.696411 0.058 Uiso 1 1 calc R . . . .
C5 C 0.4365(3) 0.2026(3) 0.6951(3) 0.0368(9) Uani 1 1 d . . . . .
C6 C 0.4802(3) 0.2075(4) 0.7950(3) 0.0436(10) Uani 1 1 d . . . . .
H6 H 0.434253 0.179378 0.834886 0.052 Uiso 1 1 calc R . . . .
C7 C 0.5903(3) 0.2527(4) 0.8383(3) 0.0418(9) Uani 1 1 d . . . . .
H7 H 0.618414 0.256312 0.907352 0.050 Uiso 1 1 calc R . . . .
C8 C 0.6590(3) 0.2925(3) 0.7818(3) 0.0358(8) Uani 1 1 d . . . . .
C9 C 0.6167(3) 0.2869(3) 0.6807(3) 0.0372(8) Uani 1 1 d . . . . .
H9 H 0.663198 0.313300 0.640669 0.045 Uiso 1 1 calc R . . . .
C10 C 0.5062(3) 0.2426(3) 0.6390(3) 0.0368(8) Uani 1 1 d . . . . .
H10 H 0.477438 0.239624 0.569952 0.044 Uiso 1 1 calc R . . . .
C11 C 0.8430(3) 0.2909(3) 0.9036(3) 0.0374(9) Uani 1 1 d . . . . .
C12 C 0.8385(4) 0.1797(4) 0.9087(3) 0.0507(11) Uani 1 1 d . . . . .
H12 H 0.785144 0.134569 0.859469 0.061 Uiso 1 1 calc R . . . .
C13 C 0.9102(4) 0.1338(4) 0.9840(4) 0.0566(12) Uani 1 1 d . . . . .
H13 H 0.905730 0.057500 0.987594 0.068 Uiso 1 1 calc R . . . .
C14 C 0.9889(4) 0.2000(4) 1.0545(3) 0.0465(10) Uani 1 1 d . . . . .
C15 C 0.9940(3) 0.3101(4) 1.0523(3) 0.0433(9) Uani 1 1 d . . . . .
H15 H 1.047482 0.354702 1.101810 0.052 Uiso 1 1 calc R . . . .
C16 C 0.9199(3) 0.3559(3) 0.9768(3) 0.0388(9) Uani 1 1 d . . . . .
H16 H 0.921956 0.432244 0.975361 0.047 Uiso 1 1 calc R . . . .
C17 C 0.8166(3) 0.4285(3) 0.7818(3) 0.0368(8) Uani 1 1 d . . . . .
C18 C 0.9224(3) 0.4304(3) 0.7638(3) 0.0381(9) Uani 1 1 d . . . . .
H18 H 0.966921 0.372843 0.783475 0.046 Uiso 1 1 calc R . . . .
C19 C 0.9633(3) 0.5156(3) 0.7174(3) 0.0366(8) Uani 1 1 d . . . . .
H19 H 1.035921 0.516133 0.705996 0.044 Uiso 1 1 calc R . . . .
C20 C 0.8995(3) 0.6003(3) 0.6872(3) 0.0341(8) Uani 1 1 d . . . . .
C21 C 0.7948(3) 0.5991(3) 0.7073(3) 0.0377(9) Uani 1 1 d . . . . .
H21 H 0.750706 0.657118 0.688414 0.045 Uiso 1 1 calc R . . . .
C22 C 0.7542(3) 0.5145(3) 0.7545(3) 0.0390(9) Uani 1 1 d . . . . .
H22 H 0.682895 0.515432 0.768274 0.047 Uiso 1 1 calc R . . . .
C23 C 0.9386(3) 0.6900(3) 0.6307(3) 0.0385(9) Uani 1 1 d . . . . .
H23A H 0.934328 0.760369 0.662473 0.046 Uiso 1 1 calc R . . . .
H23B H 1.018555 0.685221 0.631657 0.046 Uiso 1 1 calc R . . . .
C24 C 0.2953(3) 0.5042(3) 0.6217(3) 0.0364(8) Uani 1 1 d . . . . .
C25 C 0.3543(4) 0.4816(3) 0.5424(3) 0.0465(10) Uani 1 1 d . . . . .
H25A H 0.382723 0.410883 0.550984 0.070 Uiso 1 1 calc GR . . . .
H25B H 0.417751 0.537637 0.547316 0.070 Uiso 1 1 calc GR . . . .
H25C H 0.300279 0.481884 0.478050 0.070 Uiso 1 1 calc GR . . . .
C26 C 0.2504(4) 0.6130(4) 0.6084(4) 0.0582(12) Uani 1 1 d . . . . .
H26A H 0.196842 0.613206 0.543797 0.087 Uiso 1 1 calc GR . . . .
H26B H 0.313440 0.669623 0.613953 0.087 Uiso 1 1 calc GR . . . .
H26C H 0.211737 0.626754 0.658820 0.087 Uiso 1 1 calc GR . . . .
C27 C 0.3827(4) 0.5061(4) 0.7212(4) 0.0568(12) Uani 1 1 d . . . . .
H27A H 0.343883 0.506399 0.773219 0.085 Uiso 1 1 calc GR . . . .
H27B H 0.436767 0.571182 0.729294 0.085 Uiso 1 1 calc GR . . . .
H27C H 0.423104 0.441953 0.724774 0.085 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.7321(4) 0.2815(2) 0.1223(2) 0.0835(9) Uani 0.783(7) 1 d D . P A 1
Cl2 Cl 0.6155(4) 0.0708(3) 0.0577(3) 0.1196(12) Uani 0.783(7) 1 d D . P A 1
Cl3 Cl 0.8010(4) 0.1047(3) 0.2306(4) 0.149(2) Uani 0.783(7) 1 d D . P A 1
C31 C 0.6794(8) 0.1586(7) 0.1593(6) 0.095(3) Uani 0.783(7) 1 d D . P A 1
H31 H 0.624959 0.169985 0.198852 0.114 Uiso 0.783(7) 1 calc R . P A 1
Cl4 Cl 0.6860(12) 0.2684(10) 0.1277(9) 0.0835(9) Uani 0.217(7) 1 d D . P A 2
Cl5 Cl 0.6599(14) 0.0391(11) 0.0732(11) 0.1196(12) Uani 0.217(7) 1 d D . P A 2
Cl6 Cl 0.7352(10) 0.1159(5) 0.2683(5) 0.073(3) Uani 0.217(7) 1 d D . P A 2
C32 C 0.739(2) 0.1445(15) 0.1465(13) 0.095(3) Uani 0.217(7) 1 d D . P A 2
H32 H 0.819021 0.150446 0.141267 0.114 Uiso 0.217(7) 1 calc R . P A 2
Cl7 Cl -0.0105(3) -0.0856(3) 0.3043(3) 0.1147(14) Uani 0.625(3) 1 d D . P B 1
Cl8 Cl 0.2181(3) -0.1266(3) 0.3779(3) 0.1002(10) Uani 0.625(3) 1 d D . P B 1
Cl9 Cl 0.0717(4) -0.1280(3) 0.5054(3) 0.0929(11) Uani 0.625(3) 1 d D . P B 1
C33 C 0.1052(9) -0.0719(13) 0.4043(7) 0.0470(12) Uani 0.625(3) 1 d D . P B 1
H33 H 0.128243 0.007079 0.420181 0.056 Uiso 0.625(3) 1 calc R . P B 1
Cl10 Cl -0.0366(4) -0.0578(6) 0.3716(6) 0.093(2) Uani 0.293(3) 1 d D . P C 2
Cl11 Cl 0.1338(9) -0.1256(6) 0.2948(6) 0.114(3) Uani 0.293(3) 1 d D . P C 2
Cl12 Cl 0.1456(8) -0.1491(6) 0.4979(5) 0.108(3) Uani 0.293(3) 1 d D . P C 2
C34 C 0.1080(18) -0.069(3) 0.3982(13) 0.0470(12) Uani 0.293(3) 1 d D . P C 2
H34 H 0.151237 0.004843 0.414198 0.056 Uiso 0.293(3) 1 calc R . P C 2
Cl31 Cl 0.2702(14) -0.1075(14) 0.4732(17) 0.085(7) Uani 0.082(3) 1 d D . P D 3
Cl32 Cl 0.087(2) -0.108(3) 0.2992(14) 0.114(3) Uani 0.082(3) 1 d D . P D 3
Cl33 Cl 0.0418(18) -0.109(3) 0.487(2) 0.0929(11) Uani 0.082(3) 1 d D . P D 3
C41 C 0.138(2) -0.064(3) 0.4218(19) 0.0470(12) Uani 0.082(3) 1 d D . P D 3
H41 H 0.146945 0.016935 0.425578 0.056 Uiso 0.082(3) 1 calc R . P D 3
Cl13 Cl 0.744(2) 0.5501(14) 0.0237(17) 0.156(7) Uani 0.326(17) 1 d D . P E 1
Cl14 Cl 0.5910(15) 0.6997(18) -0.0308(12) 0.166(8) Uani 0.326(17) 1 d D . P E 1
Cl15 Cl 0.8113(13) 0.762(2) 0.0947(10) 0.195(8) Uani 0.326(17) 1 d D . P E 1
C35 C 0.733(2) 0.6834(17) -0.009(2) 0.099(3) Uani 0.326(17) 1 d D . P E 1
H35 H 0.762537 0.699216 -0.066993 0.118 Uiso 0.326(17) 1 calc R . P E 1
Cl16 Cl 0.7873(4) 0.5805(6) 0.0751(6) 0.1137(18) Uani 0.674(17) 1 d D . P E 2
Cl17 Cl 0.5858(6) 0.6561(14) -0.0434(8) 0.211(5) Uani 0.674(17) 1 d D . P E 2
Cl18 Cl 0.7710(8) 0.8021(5) 0.0685(6) 0.134(3) Uani 0.674(17) 1 d D . P E 2
C36 C 0.7288(11) 0.6807(11) 0.0028(12) 0.099(3) Uani 0.674(17) 1 d D . P E 2
H36 H 0.762622 0.683956 -0.053844 0.118 Uiso 0.674(17) 1 calc R . P E 2
Cl19 Cl 0.3559(4) 0.1086(4) 0.3605(3) 0.0519(12) Uani 0.266(3) 1 d D . P F 1
Cl20 Cl 0.4055(5) 0.0777(6) 0.1763(4) 0.0773(18) Uani 0.266(3) 1 d D . P F 1
Cl21 Cl 0.5853(3) 0.0952(4) 0.3550(4) 0.0619(14) Uani 0.266(3) 1 d D . P F 1
C37 C 0.4444(9) 0.0377(11) 0.3023(8) 0.029(3) Uani 0.266(3) 1 d D U P F 1
H37 H 0.433876 -0.042349 0.307805 0.034 Uiso 0.266(3) 1 calc R . P F 1
Cl22 Cl 0.4445(15) 0.2450(8) 0.3186(12) 0.081(6) Uani 0.309(3) 1 d D . P G 2
Cl23 Cl 0.519(3) 0.0673(13) 0.4328(11) 0.111(4) Uani 0.309(3) 1 d D . P G 2
Cl24 Cl 0.3832(9) 0.0274(7) 0.2350(7) 0.0657(18) Uani 0.309(3) 1 d D . P G 2
C38 C 0.407(3) 0.1108(14) 0.3400(15) 0.072(3) Uani 0.309(3) 1 d D . P G 2
H38 H 0.336683 0.105868 0.363018 0.087 Uiso 0.309(3) 1 calc R . P G 2
Cl25 Cl 0.5495(8) 0.1185(9) 0.4107(8) 0.086(3) Uani 0.200(3) 1 d D . P H 3
Cl26 Cl 0.4208(10) 0.2281(11) 0.2512(11) 0.105(5) Uani 0.200(3) 1 d D . P H 3
Cl27 Cl 0.3549(10) 0.0047(8) 0.2760(16) 0.184(11) Uani 0.200(3) 1 d D . P H 3
C39 C 0.414(2) 0.1294(16) 0.3343(19) 0.072(3) Uani 0.200(3) 1 d D . P H 3
H39 H 0.364556 0.151496 0.375713 0.087 Uiso 0.200(3) 1 calc R . P H 3
Cl28 Cl 0.459(2) 0.2443(12) 0.3474(13) 0.052(3) Uani 0.226(3) 1 d D . P I 4
Cl29 Cl 0.4006(15) 0.0533(12) 0.2186(11) 0.0657(18) Uani 0.226(3) 1 d D . P I 4
Cl30 Cl 0.506(5) 0.0384(19) 0.4231(16) 0.111(4) Uani 0.226(3) 1 d D . P I 4
C40 C 0.410(3) 0.1063(19) 0.3353(17) 0.072(3) Uani 0.226(3) 1 d D . P I 4
H40 H 0.333801 0.095982 0.347934 0.087 Uiso 0.226(3) 1 calc R . P I 4
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'
Cl Cl 0.1484 0.1585 '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 C2 123.5(3) . .
C1 N1 C23 120.3(3) . 2_666
C23 N1 C2 115.7(3) 2_666 .
C1 N2 C3 121.2(3) . .
C1 N2 C4 120.7(3) . .
C3 N2 C4 116.6(3) . .
C2 N3 C24 117.3(3) . .
C3 N3 C2 107.1(3) . .
C3 N3 C24 119.4(3) . .
C11 N4 C8 120.9(3) . .
C11 N4 C17 119.6(3) . .
C17 N4 C8 118.9(3) . .
O1 C1 N1 121.8(4) . .
O1 C1 N2 122.9(3) . .
N2 C1 N1 115.2(3) . .
N1 C2 H2A 108.8 . .
N1 C2 H2B 108.8 . .
N3 C2 N1 113.8(3) . .
N3 C2 H2A 108.8 . .
N3 C2 H2B 108.8 . .
H2A C2 H2B 107.7 . .
N2 C3 H3A 108.9 . .
N2 C3 H3B 108.9 . .
N3 C3 N2 113.3(3) . .
N3 C3 H3A 108.9 . .
N3 C3 H3B 108.9 . .
H3A C3 H3B 107.7 . .
N2 C4 H4A 109.4 . .
N2 C4 H4B 109.4 . .
N2 C4 C5 111.3(3) . .
H4A C4 H4B 108.0 . .
C5 C4 H4A 109.4 . .
C5 C4 H4B 109.4 . .
C6 C5 C4 121.9(4) . .
C6 C5 C10 118.1(3) . .
C10 C5 C4 120.0(4) . .
C5 C6 H6 119.5 . .
C5 C6 C7 121.1(4) . .
C7 C6 H6 119.5 . .
C6 C7 H7 119.8 . .
C8 C7 C6 120.4(4) . .
C8 C7 H7 119.8 . .
C7 C8 N4 120.8(3) . .
C7 C8 C9 119.2(3) . .
C9 C8 N4 120.0(3) . .
C8 C9 H9 120.3 . .
C10 C9 C8 119.5(4) . .
C10 C9 H9 120.3 . .
C5 C10 C9 121.7(3) . .
C5 C10 H10 119.1 . .
C9 C10 H10 119.1 . .
C12 C11 N4 121.7(4) . .
C12 C11 C16 119.0(4) . .
C16 C11 N4 119.2(4) . .
C11 C12 H12 119.6 . .
C13 C12 C11 120.9(4) . .
C13 C12 H12 119.6 . .
C12 C13 H13 120.4 . .
C12 C13 C14 119.2(4) . .
C14 C13 H13 120.4 . .
C13 C14 Br1 119.0(3) . .
C15 C14 Br1 119.8(3) . .
C15 C14 C13 121.2(4) . .
C14 C15 H15 120.4 . .
C14 C15 C16 119.2(4) . .
C16 C15 H15 120.4 . .
C11 C16 C15 120.4(4) . .
C11 C16 H16 119.8 . .
C15 C16 H16 119.8 . .
C18 C17 N4 121.2(4) . .
C22 C17 N4 120.0(3) . .
C22 C17 C18 118.8(4) . .
C17 C18 H18 119.8 . .
C19 C18 C17 120.4(4) . .
C19 C18 H18 119.8 . .
C18 C19 H19 119.5 . .
C18 C19 C20 120.9(4) . .
C20 C19 H19 119.5 . .
C19 C20 C21 118.4(4) . .
C19 C20 C23 121.9(3) . .
C21 C20 C23 119.7(3) . .
C20 C21 H21 119.6 . .
C22 C21 C20 120.8(4) . .
C22 C21 H21 119.6 . .
C17 C22 H22 119.7 . .
C21 C22 C17 120.6(4) . .
C21 C22 H22 119.7 . .
N1 C23 C20 111.5(3) 2_666 .
N1 C23 H23A 109.3 2_666 .
N1 C23 H23B 109.3 2_666 .
C20 C23 H23A 109.3 . .
C20 C23 H23B 109.3 . .
H23A C23 H23B 108.0 . .
N3 C24 C25 114.8(3) . .
N3 C24 C26 107.1(3) . .
N3 C24 C27 107.6(3) . .
C25 C24 C27 108.2(3) . .
C26 C24 C25 109.8(4) . .
C26 C24 C27 109.2(4) . .
C24 C25 H25A 109.5 . .
C24 C25 H25B 109.5 . .
C24 C25 H25C 109.5 . .
H25A C25 H25B 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C24 C26 H26A 109.5 . .
C24 C26 H26B 109.5 . .
C24 C26 H26C 109.5 . .
H26A C26 H26B 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
C24 C27 H27A 109.5 . .
C24 C27 H27B 109.5 . .
C24 C27 H27C 109.5 . .
H27A C27 H27B 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
Cl1 C31 Cl2 110.2(5) . .
Cl1 C31 Cl3 104.7(5) . .
Cl1 C31 H31 110.9 . .
Cl2 C31 Cl3 109.0(6) . .
Cl2 C31 H31 110.9 . .
Cl3 C31 H31 110.9 . .
Cl4 C32 Cl6 104.2(13) . .
Cl4 C32 H32 110.3 . .
Cl5 C32 Cl4 115.2(15) . .
Cl5 C32 Cl6 106.3(13) . .
Cl5 C32 H32 110.3 . .
Cl6 C32 H32 110.3 . .
Cl7 C33 Cl8 110.7(7) . .
Cl7 C33 Cl9 111.1(7) . .
Cl7 C33 H33 107.7 . .
Cl8 C33 Cl9 111.7(7) . .
Cl8 C33 H33 107.7 . .
Cl9 C33 H33 107.7 . .
Cl10 C34 Cl12 109.0(13) . .
Cl10 C34 H34 109.7 . .
Cl11 C34 Cl10 107.2(13) . .
Cl11 C34 Cl12 111.4(14) . .
Cl11 C34 H34 109.7 . .
Cl12 C34 H34 109.7 . .
Cl31 C41 H41 108.3 . .
Cl32 C41 Cl31 110.7(14) . .
Cl32 C41 H41 108.3 . .
Cl33 C41 Cl31 110.5(14) . .
Cl33 C41 Cl32 110.7(14) . .
Cl33 C41 H41 108.3 . .
Cl13 C35 H35 112.1 . .
Cl14 C35 Cl13 105.2(16) . .
Cl14 C35 Cl15 110.0(19) . .
Cl14 C35 H35 112.1 . .
Cl15 C35 Cl13 105.0(18) . .
Cl15 C35 H35 112.1 . .
Cl16 C36 H36 107.2 . .
Cl17 C36 Cl16 113.5(9) . .
Cl17 C36 Cl18 113.3(9) . .
Cl17 C36 H36 107.2 . .
Cl18 C36 Cl16 108.2(8) . .
Cl18 C36 H36 107.2 . .
Cl19 C37 Cl20 104.1(6) . .
Cl19 C37 H37 112.9 . .
Cl20 C37 H37 112.9 . .
Cl21 C37 Cl19 106.4(7) . .
Cl21 C37 Cl20 106.9(6) . .
Cl21 C37 H37 112.9 . .
Cl22 C38 Cl23 108.4(11) . .
Cl22 C38 H38 109.2 . .
Cl23 C38 H38 109.2 . .
Cl24 C38 Cl22 111.5(12) . .
Cl24 C38 Cl23 109.3(11) . .
Cl24 C38 H38 109.2 . .
Cl25 C39 H39 108.4 . .
Cl26 C39 Cl25 110.1(13) . .
Cl26 C39 Cl27 111.7(13) . .
Cl26 C39 H39 108.4 . .
Cl27 C39 Cl25 109.8(13) . .
Cl27 C39 H39 108.4 . .
C40 Cl30 Cl30 132(4) . 2_656
Cl28 C40 Cl30 108.4(12) . .
Cl28 C40 H40 109.2 . .
Cl29 C40 Cl28 111.0(13) . .
Cl29 C40 Cl30 109.7(13) . .
Cl29 C40 H40 109.2 . .
Cl30 C40 H40 109.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C14 1.898(4) .
O1 C1 1.240(5) .
N1 C1 1.366(5) .
N1 C2 1.467(5) .
N1 C23 1.460(5) 2_666
N2 C1 1.359(5) .
N2 C3 1.462(5) .
N2 C4 1.463(5) .
N3 C2 1.438(5) .
N3 C3 1.435(5) .
N3 C24 1.493(5) .
N4 C8 1.418(5) .
N4 C11 1.416(5) .
N4 C17 1.418(5) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C4 C5 1.509(5) .
C5 C6 1.378(6) .
C5 C10 1.383(6) .
C6 H6 0.9500 .
C6 C7 1.387(6) .
C7 H7 0.9500 .
C7 C8 1.378(6) .
C8 C9 1.392(5) .
C9 H9 0.9500 .
C9 C10 1.384(5) .
C10 H10 0.9500 .
C11 C12 1.386(6) .
C11 C16 1.388(5) .
C12 H12 0.9500 .
C12 C13 1.373(6) .
C13 H13 0.9500 .
C13 C14 1.384(6) .
C14 C15 1.370(6) .
C15 H15 0.9500 .
C15 C16 1.388(5) .
C16 H16 0.9500 .
C17 C18 1.391(5) .
C17 C22 1.386(6) .
C18 H18 0.9500 .
C18 C19 1.383(6) .
C19 H19 0.9500 .
C19 C20 1.389(5) .
C20 C21 1.391(5) .
C20 C23 1.503(6) .
C21 H21 0.9500 .
C21 C22 1.383(6) .
C22 H22 0.9500 .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 C25 1.529(6) .
C24 C26 1.514(6) .
C24 C27 1.534(6) .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
Cl1 C31 1.749(9) .
Cl2 C31 1.749(9) .
Cl3 C31 1.778(10) .
C31 H31 1.0000 .
Cl4 C32 1.737(19) .
Cl5 C32 1.706(18) .
Cl6 C32 1.789(19) .
C32 H32 1.0000 .
Cl7 C33 1.719(11) .
Cl8 C33 1.730(10) .
Cl9 C33 1.741(11) .
C33 H33 1.0000 .
Cl10 C34 1.740(19) .
Cl11 C34 1.736(19) .
Cl12 C34 1.745(19) .
C34 H34 1.0000 .
Cl31 C41 1.75(2) .
Cl31 Cl25 2.41(2) 2_656
Cl32 C41 1.75(2) .
Cl33 C41 1.74(2) .
C41 H41 1.0000 .
Cl13 C35 1.744(19) .
Cl14 C35 1.73(2) .
Cl15 C35 1.74(2) .
C35 H35 1.0000 .
Cl16 C36 1.729(12) .
Cl17 C36 1.702(12) .
Cl18 C36 1.717(13) .
C36 H36 1.0000 .
Cl19 C37 1.814(11) .
Cl20 C37 1.823(12) .
Cl21 C37 1.768(11) .
C37 H37 1.0000 .
Cl22 C38 1.744(16) .
Cl23 C38 1.782(17) .
Cl24 C38 1.742(17) .
C38 H38 1.0000 .
Cl25 C39 1.76(2) .
Cl26 C39 1.74(2) .
Cl27 C39 1.740(19) .
C39 H39 1.0000 .
Cl28 C40 1.753(18) .
Cl29 C40 1.742(19) .
Cl30 Cl30 2.44(7) 2_656
Cl30 C40 1.775(19) .
C40 H40 1.0000 .
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 C14 C15 C16 177.5(3) . .
N2 C4 C5 C6 112.5(4) . .
N2 C4 C5 C10 -65.4(5) . .
N4 C8 C9 C10 -178.7(4) . .
N4 C11 C12 C13 178.8(4) . .
N4 C11 C16 C15 -177.7(4) . .
N4 C17 C18 C19 177.3(3) . .
N4 C17 C22 C21 -176.8(3) . .
C1 N1 C2 N3 24.5(5) . .
C1 N2 C3 N3 -38.0(5) . .
C1 N2 C4 C5 120.5(4) . .
C2 N1 C1 O1 180.0(3) . .
C2 N1 C1 N2 -2.1(5) . .
C2 N3 C3 N2 56.5(4) . .
C2 N3 C24 C25 -54.1(4) . .
C2 N3 C24 C26 68.0(4) . .
C2 N3 C24 C27 -174.7(3) . .
C3 N2 C1 O1 -173.4(3) . .
C3 N2 C1 N1 8.7(5) . .
C3 N2 C4 C5 -73.6(5) . .
C3 N3 C2 N1 -49.9(4) . .
C3 N3 C24 C25 78.0(4) . .
C3 N3 C24 C26 -159.8(4) . .
C3 N3 C24 C27 -42.5(5) . .
C4 N2 C1 O1 -8.2(5) . .
C4 N2 C1 N1 173.9(3) . .
C4 N2 C3 N3 156.2(3) . .
C4 C5 C6 C7 -176.9(4) . .
C4 C5 C10 C9 177.7(4) . .
C5 C6 C7 C8 -1.0(6) . .
C6 C5 C10 C9 -0.3(6) . .
C6 C7 C8 N4 179.4(4) . .
C6 C7 C8 C9 0.1(6) . .
C7 C8 C9 C10 0.6(6) . .
C8 N4 C11 C12 34.7(6) . .
C8 N4 C11 C16 -145.3(4) . .
C8 N4 C17 C18 -130.8(4) . .
C8 N4 C17 C22 48.1(5) . .
C8 C9 C10 C5 -0.6(6) . .
C10 C5 C6 C7 1.0(6) . .
C11 N4 C8 C7 44.1(6) . .
C11 N4 C8 C9 -136.6(4) . .
C11 N4 C17 C18 40.7(5) . .
C11 N4 C17 C22 -140.5(4) . .
C11 C12 C13 C14 -1.1(8) . .
C12 C11 C16 C15 2.2(6) . .
C12 C13 C14 Br1 -176.4(4) . .
C12 C13 C14 C15 2.2(8) . .
C13 C14 C15 C16 -1.2(7) . .
C14 C15 C16 C11 -1.1(6) . .
C16 C11 C12 C13 -1.2(7) . .
C17 N4 C8 C7 -144.5(4) . .
C17 N4 C8 C9 34.7(6) . .
C17 N4 C11 C12 -136.6(4) . .
C17 N4 C11 C16 43.4(5) . .
C17 C18 C19 C20 -0.5(6) . .
C18 C17 C22 C21 2.1(6) . .
C18 C19 C20 C21 1.9(5) . .
C18 C19 C20 C23 -175.8(3) . .
C19 C20 C21 C22 -1.3(5) . .
C19 C20 C23 N1 109.9(4) . 2_666
C20 C21 C22 C17 -0.7(6) . .
C21 C20 C23 N1 -67.7(4) . 2_666
C22 C17 C18 C19 -1.5(6) . .
C23 N1 C1 O1 8.7(5) 2_666 .
C23 N1 C1 N2 -173.3(3) 2_666 .
C23 N1 C2 N3 -163.9(3) 2_666 .
C23 C20 C21 C22 176.5(3) . .
C24 N3 C2 N1 87.6(4) . .
C24 N3 C3 N2 -79.9(4) . .
Cl25 Cl31 C41 Cl32 166(3) 2_656 .
Cl25 Cl31 C41 Cl33 -71(5) 2_656 .
Cl30 Cl30 C40 Cl28 105(3) 2_656 .
Cl30 Cl30 C40 Cl29 -133(3) 2_656 .
