#------------------------------------------------------------------------------
#$Date: 2019-11-08 00:20:17 +0200 (Fri, 08 Nov 2019) $
#$Revision: 224230 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/96/7049682.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_7049682
loop_
_publ_author_name
'Xu, Xingyu'
'Zhang, Zengyu'
'Huang, Shiqing'
'Cao, Lei'
'Liu, Wei'
'Yan, Xiaoyu'
_publ_section_title
;
 4-Halo-1,2,3-triazolylidenes: stable carbenes featuring halogen bonding.
;
_journal_issue                   20
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6931
_journal_page_last               6941
_journal_paper_doi               10.1039/c9dt01018a
_journal_volume                  48
_journal_year                    2019
_chemical_formula_moiety         '2(C26 H34 Br Cu I N3)'
_chemical_formula_sum            'C52 H68 Br2 Cu2 I2 N6'
_chemical_formula_weight         1317.82
_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             2018-05-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2018-07-24 deposited with the CCDC.    2019-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                102.049(2)
_cell_angle_beta                 99.133(2)
_cell_angle_gamma                107.604(2)
_cell_formula_units_Z            2
_cell_length_a                   12.5144(10)
_cell_length_b                   15.6168(12)
_cell_length_c                   15.7106(12)
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      26.797
_cell_measurement_theta_min      2.307
_cell_volume                     2779.9(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 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      199.99
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0861
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            37050
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.224
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.351
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0859 before and 0.0563 after correction. The Ratio of minimum to maximum transmission is 0.7756. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   0.7456
_exptl_transmission_factor_min   0.5783
_refine_diff_density_max         1.363
_refine_diff_density_min         -1.106
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     593
_refine_ls_number_reflns         12722
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0526
_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)+(0.0346P)²+5.1741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1134
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7844
_reflns_number_total             12722
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt01018a2.cif
_cod_data_source_block           mo_hsq20171115_0m
_cod_depositor_comments
'Adding full bibliography for 7049675--7049689.cif.'
_cod_database_code               7049682
_shelx_shelxl_version_number     2016/6
_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   0.616
_shelx_estimated_absorpt_t_min   0.540
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C44, C45, C50, C51, C52
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C28, C26, C27
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C51) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(C28) \\sim Ueq: with sigma of
0.001 and sigma for terminal atoms of 0.002
Uanis(C45) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
4.a Ternary CH refined with riding coordinates:
 C20(H20), C17(H17), C47(H47), C23(H23), C41(H41), C50(H50), C44(H44), C26(H26)
4.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C33(H33), C8(H8), C7(H7), C15(H15), C31(H31), C13(H13), C39(H39),
 C32(H32), C14(H14), C38(H38), C37(H37)
4.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C25(H25A,H25B,H25C), C22(H22A,H22B,H22C), C19(H19A,H19B,
 H19C), C24(H24A,H24B,H24C), C42(H42A,H42B,H42C), C49(H49A,H49B,H49C), C48(H48A,
 H48B,H48C), C43(H43A,H43B,H43C), C18(H18A,H18B,H18C), C27(H27A,H27B,H27C),
 C46(H46A,H46B,H46C), C45(H45A,H45B,H45C), C51(H51A,H51B,H51C), C28(H28A,H28B,
 H28C), C52(H52A,H52B,H52C)
;
_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
I1 I -0.09242(4) -0.04778(3) 0.09389(3) 0.04355(12) Uani 1 1 d . .
I2 I 0.66669(3) 0.53723(3) 0.47442(3) 0.05019(13) Uani 1 1 d . .
Br1 Br -0.21969(5) 0.16983(4) 0.15492(4) 0.04558(17) Uani 1 1 d . .
Br2 Br 0.37973(6) 0.70598(4) 0.70870(4) 0.04435(17) Uani 1 1 d . .
Cu1 Cu -0.01167(6) 0.09011(4) 0.02913(4) 0.03333(17) Uani 1 1 d . .
Cu2 Cu 0.52310(6) 0.60078(4) 0.53721(4) 0.03538(17) Uani 1 1 d . .
N1 N 0.0345(3) 0.2930(3) 0.0533(3) 0.0239(9) Uani 1 1 d . .
N4 N 0.5824(3) 0.8051(3) 0.5577(3) 0.0236(9) Uani 1 1 d . .
N3 N -0.0821(4) 0.3318(3) 0.1198(3) 0.0257(9) Uani 1 1 d . .
N6 N 0.4954(3) 0.8559(3) 0.6471(3) 0.0253(9) Uani 1 1 d . .
N2 N 0.0054(4) 0.3671(3) 0.0845(3) 0.0265(9) Uani 1 1 d . .
N5 N 0.5637(3) 0.8833(3) 0.5941(3) 0.0258(9) Uani 1 1 d . .
C2 C -0.1045(4) 0.2390(3) 0.1104(3) 0.0270(11) Uani 1 1 d . .
C16 C 0.1082(4) 0.3026(3) -0.0805(3) 0.0278(12) Uani 1 1 d . .
C4 C 0.4738(4) 0.7645(3) 0.6422(3) 0.0283(12) Uani 1 1 d . .
C11 C 0.1308(4) 0.3077(3) 0.0112(3) 0.0256(11) Uani 1 1 d . .
C1 C -0.0297(4) 0.2096(3) 0.0659(3) 0.0277(11) Uani 1 1 d . .
C35 C 0.6530(4) 0.8101(3) 0.4927(3) 0.0292(12) Uani 1 1 d . .
C29 C 0.4462(5) 0.9189(3) 0.6939(4) 0.0307(12) Uani 1 1 d . .
C12 C 0.2393(5) 0.3250(3) 0.0645(3) 0.0306(12) Uani 1 1 d . .
C3 C 0.5291(4) 0.7272(3) 0.5832(3) 0.0257(11) Uani 1 1 d . .
C20 C -0.0106(5) 0.2846(4) -0.1340(3) 0.0322(12) Uani 1 1 d . .
H20 H -0.067118 0.251483 -0.102837 0.039 Uiso 1 1 calc R .
C10 C -0.2336(4) 0.3976(3) 0.1021(4) 0.0305(12) Uani 1 1 d . .
C6 C -0.1018(5) 0.4365(4) 0.2500(3) 0.0320(12) Uani 1 1 d . .
C30 C 0.5003(5) 0.9669(3) 0.7835(3) 0.0321(13) Uani 1 1 d . .
C5 C -0.1409(5) 0.3915(3) 0.1585(3) 0.0290(12) Uani 1 1 d . .
C40 C 0.5962(5) 0.7861(4) 0.4030(3) 0.0324(13) Uani 1 1 d . .
C34 C 0.3461(4) 0.9251(4) 0.6461(4) 0.0334(13) Uani 1 1 d . .
C9 C -0.2905(5) 0.4534(4) 0.1431(4) 0.0366(13) Uani 1 1 d . .
H9 H -0.354624 0.460436 0.107608 0.044 Uiso 1 1 calc R .
C36 C 0.7727(5) 0.8381(4) 0.5233(4) 0.0372(13) Uani 1 1 d . .
C33 C 0.2974(5) 0.9833(4) 0.6940(4) 0.0420(15) Uani 1 1 d . .
H33 H 0.228773 0.989746 0.664998 0.050 Uiso 1 1 calc R .
C8 C -0.2560(5) 0.4981(4) 0.2330(4) 0.0389(14) Uani 1 1 d . .
H8 H -0.297119 0.534557 0.259086 0.047 Uiso 1 1 calc R .
C7 C -0.1618(5) 0.4905(4) 0.2859(4) 0.0382(14) Uani 1 1 d . .
H7 H -0.137965 0.522805 0.347867 0.046 Uiso 1 1 calc R .
C15 C 0.2043(5) 0.3170(4) -0.1178(4) 0.0364(14) Uani 1 1 d . .
H15 H 0.194088 0.314481 -0.179582 0.044 Uiso 1 1 calc R .
C31 C 0.4462(6) 1.0224(4) 0.8261(4) 0.0406(15) Uani 1 1 d . .
H31 H 0.478540 1.055462 0.887480 0.049 Uiso 1 1 calc R .
C13 C 0.3298(5) 0.3373(4) 0.0215(4) 0.0410(14) Uani 1 1 d . .
H13 H 0.405124 0.347768 0.054618 0.049 Uiso 1 1 calc R .
C17 C 0.2589(5) 0.3273(4) 0.1631(4) 0.0401(14) Uani 1 1 d . .
H17 H 0.186236 0.326165 0.182468 0.048 Uiso 1 1 calc R .
C47 C 0.6097(5) 0.9604(4) 0.8313(4) 0.0420(15) Uani 1 1 d . .
H47 H 0.620356 0.904126 0.795074 0.050 Uiso 1 1 calc R .
C23 C -0.2717(5) 0.3504(4) 0.0032(4) 0.0379(14) Uani 1 1 d . .
H23 H -0.212989 0.322891 -0.013776 0.046 Uiso 1 1 calc R .
C39 C 0.6654(5) 0.7906(4) 0.3416(4) 0.0421(15) Uani 1 1 d . .
H39 H 0.630067 0.775103 0.279620 0.051 Uiso 1 1 calc R .
C41 C 0.4663(5) 0.7564(4) 0.3716(4) 0.0387(14) Uani 1 1 d . .
H41 H 0.434197 0.765283 0.425893 0.046 Uiso 1 1 calc R .
C50 C 0.2929(6) 0.8736(5) 0.5491(4) 0.0589(15) Uani 1 1 d . U
H50 H 0.335009 0.830261 0.530818 0.071 Uiso 1 1 calc R .
C32 C 0.3476(6) 1.0314(4) 0.7829(5) 0.0506(17) Uani 1 1 d . .
H32 H 0.313675 1.070875 0.814325 0.061 Uiso 1 1 calc R .
C14 C 0.3127(5) 0.3348(4) -0.0679(4) 0.0448(15) Uani 1 1 d . .
H14 H 0.376377 0.345372 -0.095084 0.054 Uiso 1 1 calc R .
C44 C 0.8318(5) 0.8681(5) 0.6222(4) 0.0538(15) Uani 1 1 d . U
H44 H 0.771644 0.866320 0.657432 0.065 Uiso 1 1 calc R .
C21 C -0.0297(5) 0.3760(4) -0.1366(4) 0.0501(16) Uani 1 1 d . .
H21A H -0.021231 0.412447 -0.075524 0.075 Uiso 1 1 calc GR .
H21B H -0.107459 0.362545 -0.172349 0.075 Uiso 1 1 calc GR .
H21C H 0.027498 0.411804 -0.163786 0.075 Uiso 1 1 calc GR .
C26 C 0.0025(6) 0.4295(5) 0.3084(4) 0.0539(14) Uani 1 1 d . U
H26 H 0.028705 0.383399 0.270868 0.065 Uiso 1 1 calc R .
C25 C -0.2784(7) 0.4199(5) -0.0511(4) 0.0602(19) Uani 1 1 d . .
H25A H -0.339342 0.444519 -0.038777 0.090 Uiso 1 1 calc GR .
H25B H -0.295856 0.388406 -0.115165 0.090 Uiso 1 1 calc GR .
H25C H -0.204218 0.471461 -0.034310 0.090 Uiso 1 1 calc GR .
C38 C 0.7822(6) 0.8164(4) 0.3681(4) 0.0533(18) Uani 1 1 d . .
H38 H 0.826885 0.818289 0.324533 0.064 Uiso 1 1 calc R .
C22 C -0.0369(6) 0.2222(5) -0.2294(4) 0.0588(18) Uani 1 1 d . .
H22A H 0.011474 0.255630 -0.263718 0.088 Uiso 1 1 calc GR .
H22B H -0.118469 0.205944 -0.258359 0.088 Uiso 1 1 calc GR .
H22C H -0.020623 0.165023 -0.227196 0.088 Uiso 1 1 calc GR .
C37 C 0.8366(5) 0.8401(5) 0.4580(4) 0.0542(18) Uani 1 1 d . .
H37 H 0.918171 0.857804 0.475475 0.065 Uiso 1 1 calc R .
C19 C 0.2858(6) 0.2424(5) 0.1776(4) 0.0617(19) Uani 1 1 d . .
H19A H 0.222614 0.185564 0.141071 0.093 Uiso 1 1 calc GR .
H19B H 0.294452 0.243714 0.241014 0.093 Uiso 1 1 calc GR .
H19C H 0.357698 0.242896 0.160106 0.093 Uiso 1 1 calc GR .
C24 C -0.3873(6) 0.2711(5) -0.0196(5) 0.0626(19) Uani 1 1 d . .
H24A H -0.381454 0.226840 0.015356 0.094 Uiso 1 1 calc GR .
H24B H -0.408084 0.238877 -0.083648 0.094 Uiso 1 1 calc GR .
H24C H -0.446867 0.296574 -0.005090 0.094 Uiso 1 1 calc GR .
C42 C 0.4153(6) 0.6533(4) 0.3211(4) 0.062(2) Uani 1 1 d . .
H42A H 0.448690 0.642165 0.269248 0.092 Uiso 1 1 calc GR .
H42B H 0.331456 0.634982 0.300622 0.092 Uiso 1 1 calc GR .
H42C H 0.433119 0.616187 0.360901 0.092 Uiso 1 1 calc GR .
C49 C 0.6058(7) 0.9472(6) 0.9244(4) 0.079(2) Uani 1 1 d . .
H49A H 0.600118 1.002967 0.962883 0.119 Uiso 1 1 calc GR .
H49B H 0.676286 0.937421 0.950282 0.119 Uiso 1 1 calc GR .
H49C H 0.538470 0.892737 0.919817 0.119 Uiso 1 1 calc GR .
C48 C 0.7129(6) 1.0454(5) 0.8350(6) 0.083(3) Uani 1 1 d . .
H48A H 0.712174 1.052644 0.774452 0.124 Uiso 1 1 calc GR .
H48B H 0.784629 1.036607 0.859459 0.124 Uiso 1 1 calc GR .
H48C H 0.707906 1.101530 0.873473 0.124 Uiso 1 1 calc GR .
C43 C 0.4304(6) 0.8156(5) 0.3139(5) 0.065(2) Uani 1 1 d . .
H43A H 0.459836 0.881218 0.348860 0.098 Uiso 1 1 calc GR .
H43B H 0.346045 0.794008 0.295083 0.098 Uiso 1 1 calc GR .
H43C H 0.462505 0.809324 0.260895 0.098 Uiso 1 1 calc GR .
C18 C 0.3546(8) 0.4148(5) 0.2200(5) 0.087(3) Uani 1 1 d . .
H18A H 0.427685 0.415011 0.204942 0.130 Uiso 1 1 calc GR .
H18B H 0.360318 0.416952 0.283407 0.130 Uiso 1 1 calc GR .
H18C H 0.338074 0.469459 0.208761 0.130 Uiso 1 1 calc GR .
C27 C -0.0239(7) 0.3954(6) 0.3870(5) 0.083(2) Uani 1 1 d . U
H27A H -0.050229 0.439145 0.425105 0.125 Uiso 1 1 calc GR .
H27B H 0.045761 0.391015 0.421525 0.125 Uiso 1 1 calc GR .
H27C H -0.084663 0.333692 0.366260 0.125 Uiso 1 1 calc GR .
C46 C 0.8935(7) 0.8033(5) 0.6459(5) 0.072(2) Uani 1 1 d . .
H46A H 0.837739 0.739658 0.631076 0.108 Uiso 1 1 calc GR .
H46B H 0.929952 0.824306 0.710233 0.108 Uiso 1 1 calc GR .
H46C H 0.952780 0.803905 0.611865 0.108 Uiso 1 1 calc GR .
C45 C 0.9165(7) 0.9673(6) 0.6480(6) 0.087(2) Uani 1 1 d . U
H45A H 0.976130 0.970445 0.613916 0.130 Uiso 1 1 calc GR .
H45B H 0.952734 0.986632 0.712239 0.130 Uiso 1 1 calc GR .
H45C H 0.875522 1.009114 0.634418 0.130 Uiso 1 1 calc GR .
C51 C 0.3048(8) 0.9376(6) 0.4910(6) 0.098(2) Uani 1 1 d . U
H51A H 0.250825 0.971316 0.498060 0.147 Uiso 1 1 calc GR .
H51B H 0.287349 0.901424 0.428359 0.147 Uiso 1 1 calc GR .
H51C H 0.383922 0.982299 0.508113 0.147 Uiso 1 1 calc GR .
C28 C 0.1011(8) 0.5218(6) 0.3398(6) 0.097(2) Uani 1 1 d . U
H28A H 0.126278 0.539201 0.287855 0.145 Uiso 1 1 calc GR .
H28B H 0.165559 0.516201 0.379928 0.145 Uiso 1 1 calc GR .
H28C H 0.075507 0.569925 0.371839 0.145 Uiso 1 1 calc GR .
C52 C 0.1675(8) 0.8160(7) 0.5313(6) 0.105(2) Uani 1 1 d . U
H52A H 0.157326 0.775871 0.571953 0.157 Uiso 1 1 calc GR .
H52B H 0.140672 0.777113 0.469149 0.157 Uiso 1 1 calc GR .
H52C H 0.122736 0.857325 0.541252 0.157 Uiso 1 1 calc GR .
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
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
Cu1 I1 Cu1 68.23(2) . 2
Cu2 I2 Cu2 69.89(3) . 2_666
I1 Cu1 I1 111.77(2) . 2
I1 Cu1 Cu1 56.00(2) . 2
I1 Cu1 Cu1 55.77(2) 2 2
C1 Cu1 I1 123.99(15) . 2
C1 Cu1 I1 124.22(15) . .
C1 Cu1 Cu1 178.85(16) . 2
I2 Cu2 I2 110.11(3) . 2_666
I2 Cu2 Cu2 53.51(2) 2_666 2_666
I2 Cu2 Cu2 56.60(2) . 2_666
C3 Cu2 I2 131.29(15) . .
C3 Cu2 I2 118.51(15) . 2_666
C3 Cu2 Cu2 171.63(15) . 2_666
N2 N1 C11 117.4(4) . .
N2 N1 C1 116.4(4) . .
C1 N1 C11 126.2(4) . .
N5 N4 C35 117.0(4) . .
N5 N4 C3 116.5(4) . .
C3 N4 C35 126.4(4) . .
N2 N3 C2 110.9(4) . .
N2 N3 C5 119.4(4) . .
C2 N3 C5 129.6(4) . .
N5 N6 C4 110.9(4) . .
N5 N6 C29 120.2(4) . .
C4 N6 C29 128.6(4) . .
N3 N2 N1 102.8(4) . .
N6 N5 N4 102.5(4) . .
N3 C2 Br1 121.5(4) . .
N3 C2 C1 110.1(4) . .
C1 C2 Br1 128.4(4) . .
C11 C16 C20 122.1(4) . .
C15 C16 C11 115.3(5) . .
C15 C16 C20 122.6(5) . .
N6 C4 Br2 120.8(4) . .
N6 C4 C3 110.4(4) . .
C3 C4 Br2 128.8(4) . .
C16 C11 N1 117.8(4) . .
C12 C11 N1 117.5(4) . .
C12 C11 C16 124.7(4) . .
N1 C1 Cu1 127.2(4) . .
N1 C1 C2 99.8(4) . .
C2 C1 Cu1 133.0(4) . .
C40 C35 N4 117.3(5) . .
C40 C35 C36 124.0(5) . .
C36 C35 N4 118.7(5) . .
C30 C29 N6 118.0(5) . .
C30 C29 C34 125.0(5) . .
C34 C29 N6 117.0(5) . .
C11 C12 C17 122.7(5) . .
C13 C12 C11 116.0(5) . .
C13 C12 C17 121.3(5) . .
N4 C3 Cu2 128.4(4) . .
N4 C3 C4 99.6(4) . .
C4 C3 Cu2 131.6(4) . .
C16 C20 H20 107.5 . .
C16 C20 C21 110.9(4) . .
C16 C20 C22 113.1(5) . .
C21 C20 H20 107.5 . .
C21 C20 C22 110.0(5) . .
C22 C20 H20 107.5 . .
C5 C10 C9 115.4(5) . .
C5 C10 C23 123.8(5) . .
C9 C10 C23 120.9(5) . .
C5 C6 C26 122.9(5) . .
C7 C6 C5 116.5(5) . .
C7 C6 C26 120.6(5) . .
C29 C30 C47 123.2(5) . .
C31 C30 C29 115.4(5) . .
C31 C30 C47 121.4(5) . .
C10 C5 N3 117.3(4) . .
C10 C5 C6 125.0(5) . .
C6 C5 N3 117.6(5) . .
C35 C40 C39 116.4(5) . .
C35 C40 C41 123.0(5) . .
C39 C40 C41 120.6(5) . .
C29 C34 C33 115.9(5) . .
C29 C34 C50 122.9(5) . .
C33 C34 C50 121.2(5) . .
C10 C9 H9 119.2 . .
C8 C9 C10 121.7(5) . .
C8 C9 H9 119.2 . .
C35 C36 C44 122.4(5) . .
C37 C36 C35 116.5(5) . .
C37 C36 C44 121.1(5) . .
C34 C33 H33 119.5 . .
C32 C33 C34 120.9(6) . .
C32 C33 H33 119.5 . .
C9 C8 H8 119.8 . .
C9 C8 C7 120.4(5) . .
C7 C8 H8 119.8 . .
C6 C7 H7 119.5 . .
C8 C7 C6 121.0(5) . .
C8 C7 H7 119.5 . .
C16 C15 H15 119.0 . .
C14 C15 C16 122.0(5) . .
C14 C15 H15 119.0 . .
C30 C31 H31 118.8 . .
C32 C31 C30 122.4(6) . .
C32 C31 H31 118.8 . .
C12 C13 H13 119.2 . .
C14 C13 C12 121.6(5) . .
C14 C13 H13 119.2 . .
C12 C17 H17 108.2 . .
C19 C17 C12 110.8(5) . .
C19 C17 H17 108.2 . .
C18 C17 C12 111.4(5) . .
C18 C17 H17 108.2 . .
C18 C17 C19 109.8(5) . .
C30 C47 H47 107.3 . .
C30 C47 C49 112.9(5) . .
C30 C47 C48 110.3(5) . .
C49 C47 H47 107.3 . .
C49 C47 C48 111.5(6) . .
C48 C47 H47 107.3 . .
C10 C23 H23 108.0 . .
C10 C23 C25 111.4(5) . .
C10 C23 C24 110.9(5) . .
C25 C23 H23 108.0 . .
C24 C23 H23 108.0 . .
C24 C23 C25 110.5(5) . .
C40 C39 H39 119.2 . .
C38 C39 C40 121.7(6) . .
C38 C39 H39 119.2 . .
C40 C41 H41 107.9 . .
C40 C41 C42 110.2(5) . .
C40 C41 C43 112.2(5) . .
C42 C41 H41 107.9 . .
C42 C41 C43 110.7(5) . .
C43 C41 H41 107.9 . .
C34 C50 H50 107.7 . .
C51 C50 C34 111.9(6) . .
C51 C50 H50 107.7 . .
C51 C50 C52 108.3(7) . .
C52 C50 C34 113.3(6) . .
C52 C50 H50 107.7 . .
C33 C32 H32 119.8 . .
C31 C32 C33 120.4(5) . .
C31 C32 H32 119.8 . .
C15 C14 C13 120.3(5) . .
C15 C14 H14 119.9 . .
C13 C14 H14 119.9 . .
C36 C44 H44 108.3 . .
C36 C44 C45 110.1(6) . .
C46 C44 C36 111.7(5) . .
C46 C44 H44 108.3 . .
C46 C44 C45 110.0(6) . .
C45 C44 H44 108.3 . .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21B 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C6 C26 H26 107.6 . .
C27 C26 C6 113.0(5) . .
C27 C26 H26 107.6 . .
C27 C26 C28 109.7(6) . .
C28 C26 C6 111.2(6) . .
C28 C26 H26 107.6 . .
C23 C25 H25A 109.5 . .
C23 C25 H25B 109.5 . .
C23 C25 H25C 109.5 . .
H25A C25 H25B 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C39 C38 H38 119.7 . .
C39 C38 C37 120.7(5) . .
C37 C38 H38 119.7 . .
C20 C22 H22A 109.5 . .
C20 C22 H22B 109.5 . .
C20 C22 H22C 109.5 . .
H22A C22 H22B 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C36 C37 H37 119.7 . .
C38 C37 C36 120.7(6) . .
C38 C37 H37 119.7 . .
C17 C19 H19A 109.5 . .
C17 C19 H19B 109.5 . .
C17 C19 H19C 109.5 . .
H19A C19 H19B 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C23 C24 H24A 109.5 . .
C23 C24 H24B 109.5 . .
C23 C24 H24C 109.5 . .
H24A C24 H24B 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C41 C42 H42A 109.5 . .
C41 C42 H42B 109.5 . .
C41 C42 H42C 109.5 . .
H42A C42 H42B 109.5 . .
H42A C42 H42C 109.5 . .
H42B C42 H42C 109.5 . .
C47 C49 H49A 109.5 . .
C47 C49 H49B 109.5 . .
C47 C49 H49C 109.5 . .
H49A C49 H49B 109.5 . .
H49A C49 H49C 109.5 . .
H49B C49 H49C 109.5 . .
C47 C48 H48A 109.5 . .
C47 C48 H48B 109.5 . .
C47 C48 H48C 109.5 . .
H48A C48 H48B 109.5 . .
H48A C48 H48C 109.5 . .
H48B C48 H48C 109.5 . .
C41 C43 H43A 109.5 . .
C41 C43 H43B 109.5 . .
C41 C43 H43C 109.5 . .
H43A C43 H43B 109.5 . .
H43A C43 H43C 109.5 . .
H43B C43 H43C 109.5 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C26 C27 H27A 109.5 . .
C26 C27 H27B 109.5 . .
C26 C27 H27C 109.5 . .
H27A C27 H27B 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
C44 C46 H46A 109.5 . .
C44 C46 H46B 109.5 . .
C44 C46 H46C 109.5 . .
H46A C46 H46B 109.5 . .
H46A C46 H46C 109.5 . .
H46B C46 H46C 109.5 . .
C44 C45 H45A 109.5 . .
C44 C45 H45B 109.5 . .
C44 C45 H45C 109.5 . .
H45A C45 H45B 109.5 . .
H45A C45 H45C 109.5 . .
H45B C45 H45C 109.5 . .
C50 C51 H51A 109.5 . .
C50 C51 H51B 109.5 . .
C50 C51 H51C 109.5 . .
H51A C51 H51B 109.5 . .
H51A C51 H51C 109.5 . .
H51B C51 H51C 109.5 . .
C26 C28 H28A 109.5 . .
C26 C28 H28B 109.5 . .
C26 C28 H28C 109.5 . .
H28A C28 H28B 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
C50 C52 H52A 109.5 . .
C50 C52 H52B 109.5 . .
C50 C52 H52C 109.5 . .
H52A C52 H52B 109.5 . .
H52A C52 H52C 109.5 . .
H52B C52 H52C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 Cu1 2.5727(7) .
I1 Cu1 2.5797(8) 2
I2 Cu2 2.6307(8) 2_666
I2 Cu2 2.5337(8) .
Br1 C2 1.852(5) .
Br2 C4 1.858(5) .
Cu1 Cu1 2.8898(12) 2
Cu1 C1 1.927(5) .
Cu2 Cu2 2.9591(13) 2_666
Cu2 C3 1.929(5) .
N1 N2 1.337(5) .
N1 C11 1.446(6) .
N1 C1 1.381(6) .
N4 N5 1.341(5) .
N4 C35 1.451(6) .
N4 C3 1.373(6) .
N3 N2 1.329(5) .
N3 C2 1.360(6) .
N3 C5 1.449(6) .
N6 N5 1.327(5) .
N6 C4 1.353(6) .
N6 C29 1.448(6) .
C2 C1 1.381(7) .
C16 C11 1.403(7) .
C16 C20 1.499(7) .
C16 C15 1.398(7) .
C4 C3 1.378(7) .
C11 C12 1.394(7) .
C35 C40 1.389(7) .
C35 C36 1.398(7) .
C29 C30 1.397(7) .
C29 C34 1.395(7) .
C12 C13 1.393(7) .
C12 C17 1.520(7) .
C20 H20 1.0000 .
C20 C21 1.524(7) .
C20 C22 1.532(8) .
C10 C5 1.384(7) .
C10 C9 1.403(7) .
C10 C23 1.503(7) .
C6 C5 1.395(7) .
C6 C7 1.383(7) .
C6 C26 1.519(8) .
C30 C31 1.383(7) .
C30 C47 1.497(8) .
C40 C39 1.393(7) .
C40 C41 1.516(8) .
C34 C33 1.401(8) .
C34 C50 1.501(8) .
C9 H9 0.9500 .
C9 C8 1.372(8) .
C36 C44 1.518(8) .
C36 C37 1.397(8) .
C33 H33 0.9500 .
C33 C32 1.381(9) .
C8 H8 0.9500 .
C8 C7 1.382(8) .
C7 H7 0.9500 .
C15 H15 0.9500 .
C15 C14 1.370(8) .
C31 H31 0.9500 .
C31 C32 1.372(9) .
C13 H13 0.9500 .
C13 C14 1.376(8) .
C17 H17 1.0000 .
C17 C19 1.516(8) .
C17 C18 1.504(9) .
C47 H47 1.0000 .
C47 C49 1.525(8) .
C47 C48 1.530(9) .
C23 H23 1.0000 .
C23 C25 1.528(8) .
C23 C24 1.524(8) .
C39 H39 0.9500 .
C39 C38 1.361(8) .
C41 H41 1.0000 .
C41 C42 1.522(8) .
C41 C43 1.532(8) .
C50 H50 1.0000 .
C50 C51 1.479(10) .
C50 C52 1.501(10) .
C32 H32 0.9500 .
C14 H14 0.9500 .
C44 H44 1.0000 .
C44 C46 1.516(9) .
C44 C45 1.516(10) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C26 H26 1.0000 .
C26 C27 1.488(9) .
C26 C28 1.510(10) .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
C38 H38 0.9500 .
C38 C37 1.386(9) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C37 H37 0.9500 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
C42 H42A 0.9800 .
C42 H42B 0.9800 .
C42 H42C 0.9800 .
C49 H49A 0.9800 .
C49 H49B 0.9800 .
C49 H49C 0.9800 .
C48 H48A 0.9800 .
C48 H48B 0.9800 .
C48 H48C 0.9800 .
C43 H43A 0.9800 .
C43 H43B 0.9800 .
C43 H43C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
C46 H46A 0.9800 .
C46 H46B 0.9800 .
C46 H46C 0.9800 .
C45 H45A 0.9800 .
C45 H45B 0.9800 .
C45 H45C 0.9800 .
C51 H51A 0.9800 .
C51 H51B 0.9800 .
C51 H51C 0.9800 .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
C52 H52A 0.9800 .
C52 H52B 0.9800 .
C52 H52C 0.9800 .
