#------------------------------------------------------------------------------
#$Date: 2017-06-03 01:51:46 +0300 (Sat, 03 Jun 2017) $
#$Revision: 197166 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/60/4126087.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_4126087
loop_
_publ_author_name
'Tomás-Mendivil, Eder'
'Hansmann, Max M.'
'Weinstein, Cory M.'
'Jazzar, Rodolphe'
'Melaimi, Mohand'
'Bertrand, Guy'
_publ_section_title
;
 Bicyclic (Alkyl)(amino)carbenes (BICAACs): Stable Carbenes more
 Ambiphilic than CAACs.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b04640
_journal_year                    2017
_chemical_formula_moiety         'Br2 Cu, 2(C22 H33 Cu0.5 N)'
_chemical_formula_sum            'C44 H66 Br2 Cu2 N2'
_chemical_formula_weight         909.88
_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     direct
_audit_creation_date             2017-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                102.972(5)
_cell_angle_beta                 92.218(5)
_cell_angle_gamma                112.649(5)
_cell_formula_units_Z            2
_cell_length_a                   10.4452(15)
_cell_length_b                   11.9506(19)
_cell_length_c                   18.948(3)
_cell_measurement_reflns_used    9991
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.33
_cell_measurement_theta_min      2.22
_cell_volume                     2106.4(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX CCD'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            47761
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.437
_diffrn_reflns_theta_min         1.912
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.938
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0715 before and 0.0486 after correction. The Ratio of minimum to maximum transmission is 0.8559. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_recrystallization_method DCM/Et2O
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.517
_refine_diff_density_min         -1.075
_refine_diff_density_rms         0.107
_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     468
_refine_ls_number_reflns         7741
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0443
_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)+(0.0610P)²+3.2595P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1243
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5778
_reflns_number_total             7741
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b04640_si_002.cif
_cod_data_source_block           6a
_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/ACS/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               4126087
_shelx_shelxl_version_number     2014/7
_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.
;
_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.a Ternary CH refined with riding coordinates:
 C19(H19), C3A(H3A), C19A(H19A), C16A(H16A), C16(H16), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C6A(H6AA,H6AB), C4A(H4AA,H4AB), C4(H4A,H4B), C7A(H7AA,H7AB), C6(H6A,H6B),
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C14A(H14A), C12(H12), C12A(H12A), C13(H13), C13A(H13A)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C20A(H20D,H20E,
 H20F), C22A(H22D,H22E,H22F), C8A(H8AA,H8AB,H8AC), C17(H17A,H17B,H17C),
 C20(H20A,H20B,H20C), C17A(H17D,H17E,H17F), C21A(H21D,H21E,H21F), C18(H18A,H18B,
 H18C), C18A(H18D,H18E,H18F), C9A(H9AA,H9AB,H9AC), C9(H9A,H9B,H9C)
;
_olex2_exptl_crystal_mounting_method fomblin
_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
Br2 Br 0.64672(5) 1.06812(5) 0.77688(3) 0.02753(14) Uani 1 1 d . . .
Br1 Br 0.22472(5) 0.75276(5) 0.70571(3) 0.03021(15) Uani 1 1 d . . .
Cu1 Cu 0.0000 0.0000 0.5000 0.01298(18) Uani 1 2 d S T P
Cu1A Cu 0.5000 0.5000 1.0000 0.0187(2) Uani 1 2 d S T P
Cu2 Cu 0.43540(6) 0.91112(5) 0.74045(3) 0.02255(16) Uani 1 1 d . . .
N1 N 0.1599(3) 0.2637(3) 0.55076(18) 0.0111(7) Uani 1 1 d . . .
N1A N 0.6425(3) 0.7086(3) 0.94015(18) 0.0094(7) Uani 1 1 d . . .
C10 C 0.2709(4) 0.2411(4) 0.5129(2) 0.0118(9) Uani 1 1 d . . .
C1A C 0.5225(4) 0.6191(4) 0.9415(2) 0.0127(9) Uani 1 1 d . . .
C11A C 0.8116(4) 0.8003(4) 1.0531(2) 0.0146(9) Uani 1 1 d . . .
C19 C 0.3684(4) 0.2102(4) 0.6305(2) 0.0174(10) Uani 1 1 d . . .
H19 H 0.2972 0.2411 0.6503 0.021 Uiso 1 1 calc R . .
C10A C 0.7701(4) 0.7218(4) 0.9829(2) 0.0113(9) Uani 1 1 d . . .
C6A C 0.5901(5) 0.7144(4) 0.8147(2) 0.0203(10) Uani 1 1 d . . .
H6AA H 0.5773 0.7655 0.7828 0.024 Uiso 1 1 calc R . .
H6AB H 0.6577 0.6798 0.7954 0.024 Uiso 1 1 calc R . .
C11 C 0.3730(4) 0.2202(4) 0.5524(2) 0.0165(10) Uani 1 1 d . . .
C1 C 0.0396(4) 0.1714(4) 0.5484(2) 0.0123(9) Uani 1 1 d . . .
C2A C 0.4050(4) 0.6202(4) 0.8923(2) 0.0151(10) Uani 1 1 d . . .
C4A C 0.5429(4) 0.8548(4) 0.9182(3) 0.0174(10) Uani 1 1 d . . .
H4AA H 0.5772 0.9100 0.9685 0.021 Uiso 1 1 calc R . .
H4AB H 0.5350 0.9066 0.8856 0.021 Uiso 1 1 calc R . .
C14 C 0.3815(5) 0.2208(4) 0.4052(3) 0.0210(10) Uani 1 1 d . . .
H14 H 0.3845 0.2195 0.3550 0.025 Uiso 1 1 calc R . .
C14A C 0.9703(4) 0.6714(4) 0.9923(3) 0.0197(10) Uani 1 1 d . . .
H14A H 1.0239 0.6264 0.9724 0.024 Uiso 1 1 calc R . .
C12 C 0.4793(5) 0.2004(4) 0.5149(3) 0.0197(10) Uani 1 1 d . . .
H12 H 0.5489 0.1847 0.5396 0.024 Uiso 1 1 calc R . .
C5A C 0.6482(4) 0.7976(4) 0.8933(2) 0.0149(9) Uani 1 1 d . . .
C15 C 0.2718(5) 0.2405(4) 0.4392(2) 0.0166(10) Uani 1 1 d . . .
C4 C 0.1487(5) 0.3941(4) 0.6684(2) 0.0197(10) Uani 1 1 d . . .
H4A H 0.2211 0.3781 0.6947 0.024 Uiso 1 1 calc R . .
H4B H 0.1516 0.4766 0.6949 0.024 Uiso 1 1 calc R . .
C3A C 0.3977(5) 0.7509(4) 0.9167(3) 0.0193(10) Uani 1 1 d . . .
H3A H 0.3314 0.7550 0.8788 0.023 Uiso 1 1 calc R . .
C19A C 0.7243(5) 0.8675(4) 1.0904(2) 0.0197(10) Uani 1 1 d . . .
H19A H 0.6464 0.8543 1.0529 0.024 Uiso 1 1 calc R . .
C8 C 0.3260(5) 0.4921(4) 0.5889(3) 0.0217(11) Uani 1 1 d . . .
H8A H 0.3951 0.4740 0.6154 0.032 Uiso 1 1 calc GR . .
H8B H 0.3331 0.5765 0.6126 0.032 Uiso 1 1 calc GR . .
H8C H 0.3441 0.4876 0.5382 0.032 Uiso 1 1 calc GR . .
C12A C 0.9345(4) 0.8139(4) 1.0920(3) 0.0182(10) Uani 1 1 d . . .
H12A H 0.9650 0.8674 1.1402 0.022 Uiso 1 1 calc R . .
C15A C 0.8472(4) 0.6555(4) 0.9499(2) 0.0145(9) Uani 1 1 d . . .
C16A C 0.8033(5) 0.5655(4) 0.8744(2) 0.0212(11) Uani 1 1 d . . .
H16A H 0.7163 0.5682 0.8525 0.025 Uiso 1 1 calc R . .
C2 C -0.0623(4) 0.2180(4) 0.5877(2) 0.0166(10) Uani 1 1 d . . .
C16 C 0.1595(5) 0.2574(4) 0.3943(2) 0.0206(10) Uani 1 1 d . . .
H16 H 0.0874 0.2640 0.4263 0.025 Uiso 1 1 calc R . .
C7A C 0.4494(5) 0.6065(4) 0.8138(2) 0.0204(10) Uani 1 1 d . . .
H7AA H 0.4577 0.5252 0.7972 0.024 Uiso 1 1 calc R . .
H7AB H 0.3768 0.6076 0.7791 0.024 Uiso 1 1 calc R . .
C6 C 0.0646(5) 0.4213(4) 0.5524(3) 0.0239(11) Uani 1 1 d . . .
H6A H 0.0840 0.4288 0.5026 0.029 Uiso 1 1 calc R . .
H6B H 0.0636 0.5015 0.5804 0.029 Uiso 1 1 calc R . .
C5 C 0.1804(4) 0.3967(4) 0.5899(3) 0.0180(10) Uani 1 1 d . . .
C13 C 0.4835(5) 0.2036(4) 0.4428(3) 0.0218(11) Uani 1 1 d . . .
H13 H 0.5583 0.1937 0.4190 0.026 Uiso 1 1 calc R . .
C21 C 0.5086(5) 0.2923(5) 0.6801(3) 0.0292(12) Uani 1 1 d . . .
H21A H 0.5784 0.2587 0.6657 0.044 Uiso 1 1 calc GR . .
H21B H 0.4961 0.2922 0.7311 0.044 Uiso 1 1 calc GR . .
H21C H 0.5407 0.3784 0.6751 0.044 Uiso 1 1 calc GR . .
C22 C -0.2036(4) 0.1100(4) 0.5834(3) 0.0233(11) Uani 1 1 d . . .
H22A H -0.2468 0.0725 0.5322 0.035 Uiso 1 1 calc GR . .
H22B H -0.2649 0.1418 0.6114 0.035 Uiso 1 1 calc GR . .
H22C H -0.1899 0.0463 0.6037 0.035 Uiso 1 1 calc GR . .
C3 C 0.0034(5) 0.2908(5) 0.6670(3) 0.0274(12) Uani 1 1 d . . .
H3 H -0.0573 0.3342 0.6871 0.033 Uiso 1 1 calc R . .
C13A C 1.0135(4) 0.7495(4) 1.0606(3) 0.0210(11) Uani 1 1 d . . .
H13A H 1.0981 0.7603 1.0874 0.025 Uiso 1 1 calc R . .
C20A C 0.6578(5) 0.8079(5) 1.1510(3) 0.0262(11) Uani 1 1 d . . .
H20D H 0.6060 0.7172 1.1308 0.039 Uiso 1 1 calc GR . .
H20E H 0.5934 0.8448 1.1707 0.039 Uiso 1 1 calc GR . .
H20F H 0.7314 0.8236 1.1902 0.039 Uiso 1 1 calc GR . .
C22A C 0.2663(5) 0.5123(4) 0.8912(3) 0.0258(11) Uani 1 1 d . . .
H22D H 0.2741 0.4324 0.8717 0.039 Uiso 1 1 calc GR . .
H22E H 0.1926 0.5175 0.8602 0.039 Uiso 1 1 calc GR . .
H22F H 0.2427 0.5175 0.9411 0.039 Uiso 1 1 calc GR . .
C7 C -0.0795(5) 0.3136(4) 0.5478(3) 0.0270(12) Uani 1 1 d . . .
H7A H -0.1193 0.2706 0.4959 0.032 Uiso 1 1 calc R . .
H7B H -0.1446 0.3479 0.5711 0.032 Uiso 1 1 calc R . .
C8A C 0.7949(5) 0.8974(4) 0.8986(3) 0.0231(11) Uani 1 1 d . . .
H8AA H 0.8273 0.9481 0.9492 0.035 Uiso 1 1 calc GR . .
H8AB H 0.7935 0.9514 0.8668 0.035 Uiso 1 1 calc GR . .
H8AC H 0.8584 0.8569 0.8830 0.035 Uiso 1 1 calc GR . .
C17 C 0.0865(5) 0.1430(5) 0.3284(3) 0.0295(12) Uani 1 1 d . . .
H17A H 0.1546 0.1360 0.2955 0.044 Uiso 1 1 calc GR . .
H17B H 0.0107 0.1534 0.3022 0.044 Uiso 1 1 calc GR . .
H17C H 0.0476 0.0667 0.3456 0.044 Uiso 1 1 calc GR . .
C20 C 0.3192(6) 0.0735(5) 0.6333(3) 0.0293(12) Uani 1 1 d . . .
H20A H 0.2271 0.0241 0.6037 0.044 Uiso 1 1 calc GR . .
H20B H 0.3123 0.0686 0.6840 0.044 Uiso 1 1 calc GR . .
H20C H 0.3865 0.0400 0.6139 0.044 Uiso 1 1 calc GR . .
C17A C 0.7679(6) 0.4304(5) 0.8784(3) 0.0323(13) Uani 1 1 d . . .
H17D H 0.8517 0.4246 0.8993 0.048 Uiso 1 1 calc GR . .
H17E H 0.7355 0.3738 0.8290 0.048 Uiso 1 1 calc GR . .
H17F H 0.6940 0.4063 0.9092 0.048 Uiso 1 1 calc GR . .
C21A C 0.8080(5) 1.0096(4) 1.1199(3) 0.0314(12) Uani 1 1 d . . .
H21D H 0.8816 1.0259 1.1593 0.047 Uiso 1 1 calc GR . .
H21E H 0.7452 1.0489 1.1390 0.047 Uiso 1 1 calc GR . .
H21F H 0.8508 1.0448 1.0804 0.047 Uiso 1 1 calc GR . .
C18 C 0.2193(6) 0.3777(5) 0.3685(3) 0.0317(13) Uani 1 1 d . . .
H18A H 0.2636 0.4501 0.4110 0.048 Uiso 1 1 calc GR . .
H18B H 0.1435 0.3872 0.3418 0.048 Uiso 1 1 calc GR . .
H18C H 0.2891 0.3727 0.3363 0.048 Uiso 1 1 calc GR . .
C18A C 0.9149(6) 0.6033(6) 0.8234(3) 0.0378(14) Uani 1 1 d . . .
H18D H 0.9324 0.6879 0.8190 0.057 Uiso 1 1 calc GR . .
H18E H 0.8812 0.5438 0.7750 0.057 Uiso 1 1 calc GR . .
H18F H 1.0019 0.6022 0.8438 0.057 Uiso 1 1 calc GR . .
C9A C 0.3449(5) 0.7728(5) 0.9883(3) 0.0361(13) Uani 1 1 d . . .
H9AA H 0.2537 0.7046 0.9865 0.054 Uiso 1 1 calc GR . .
H9AB H 0.3350 0.8529 0.9984 0.054 Uiso 1 1 calc GR . .
H9AC H 0.4115 0.7752 1.0272 0.054 Uiso 1 1 calc GR . .
C9 C 0.0082(6) 0.2113(6) 0.7148(3) 0.0412(14) Uani 1 1 d . . .
H9A H 0.0654 0.1656 0.6964 0.062 Uiso 1 1 calc GR . .
H9B H -0.0871 0.1513 0.7156 0.062 Uiso 1 1 calc GR . .
H9C H 0.0494 0.2639 0.7645 0.062 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'
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_3
C1 Cu1 C1 180.0 2_556
C1A Cu1A C1A 180.0 2_667
Br1 Cu2 Br2 178.97(4) .
C10 N1 C5 120.3(3) .
C1 N1 C10 120.7(3) .
C1 N1 C5 118.9(3) .
C1A N1A C10A 120.2(3) .
C1A N1A C5A 119.0(3) .
C10A N1A C5A 120.8(3) .
C11 C10 N1 118.6(4) .
C15 C10 N1 119.2(4) .
C15 C10 C11 122.3(4) .
N1A C1A Cu1A 123.2(3) .
N1A C1A C2A 111.8(4) .
C2A C1A Cu1A 125.0(3) .
C10A C11A C19A 122.6(4) .
C10A C11A C12A 118.4(4) .
C12A C11A C19A 118.9(4) .
C11 C19 H19 107.3 .
C11 C19 C21 112.9(4) .
C11 C19 C20 110.7(4) .
C21 C19 H19 107.3 .
C20 C19 H19 107.3 .
C20 C19 C21 111.0(4) .
C11A C10A N1A 119.3(3) .
C11A C10A C15A 122.6(4) .
C15A C10A N1A 118.1(4) .
H6AA C6A H6AB 108.1 .
C5A C6A H6AA 109.6 .
C5A C6A H6AB 109.6 .
C7A C6A H6AA 109.6 .
C7A C6A H6AB 109.6 .
C7A C6A C5A 110.2(3) .
C10 C11 C19 123.4(4) .
C12 C11 C10 117.3(4) .
C12 C11 C19 119.2(4) .
N1 C1 Cu1 122.9(3) .
N1 C1 C2 111.5(4) .
C2 C1 Cu1 125.6(3) .
C1A C2A C3A 108.9(4) .
C1A C2A C7A 105.9(3) .
C1A C2A C22A 111.8(4) .
C3A C2A C7A 107.5(3) .
C22A C2A C3A 112.7(4) .
C22A C2A C7A 109.8(4) .
H4AA C4A H4AB 108.1 .
C5A C4A H4AA 109.5 .
C5A C4A H4AB 109.5 .
C3A C4A H4AA 109.5 .
C3A C4A H4AB 109.5 .
C3A C4A C5A 110.8(3) .
C15 C14 H14 119.3 .
C13 C14 H14 119.3 .
C13 C14 C15 121.4(4) .
C15A C14A H14A 119.2 .
C13A C14A H14A 119.2 .
C13A C14A C15A 121.5(4) .
C11 C12 H12 119.6 .
C13 C12 C11 120.8(4) .
C13 C12 H12 119.6 .
N1A C5A C6A 105.9(3) .
N1A C5A C4A 106.4(3) .
N1A C5A C8A 112.5(3) .
C4A C5A C6A 107.0(4) .
C8A C5A C6A 112.3(4) .
C8A C5A C4A 112.3(4) .
C10 C15 C14 117.4(4) .
C10 C15 C16 123.4(4) .
C14 C15 C16 119.2(4) .
H4A C4 H4B 108.1 .
C5 C4 H4A 109.6 .
C5 C4 H4B 109.6 .
C3 C4 H4A 109.6 .
C3 C4 H4B 109.6 .
C3 C4 C5 110.3(4) .
C2A C3A H3A 107.6 .
C4A C3A C2A 109.4(3) .
C4A C3A H3A 107.6 .
C9A C3A C2A 113.5(4) .
C9A C3A C4A 110.9(4) .
C9A C3A H3A 107.6 .
C11A C19A H19A 107.4 .
C11A C19A C20A 110.1(4) .
C11A C19A C21A 112.9(4) .
C20A C19A H19A 107.4 .
C21A C19A H19A 107.4 .
C21A C19A C20A 111.3(4) .
H8A C8 H8B 109.5 .
H8A C8 H8C 109.5 .
H8B C8 H8C 109.5 .
C5 C8 H8A 109.5 .
C5 C8 H8B 109.5 .
C5 C8 H8C 109.5 .
C11A C12A H12A 119.8 .
C11A C12A C13A 120.3(4) .
C13A C12A H12A 119.8 .
C10A C15A C14A 116.6(4) .
C10A C15A C16A 124.4(4) .
C14A C15A C16A 119.0(4) .
C15A C16A H16A 107.6 .
C15A C16A C17A 111.3(4) .
C15A C16A C18A 112.3(4) .
C17A C16A H16A 107.6 .
C17A C16A C18A 110.3(4) .
C18A C16A H16A 107.6 .
C1 C2 C3 109.7(4) .
C1 C2 C7 105.8(3) .
C22 C2 C1 111.2(3) .
C22 C2 C3 112.1(4) .
C22 C2 C7 110.3(4) .
C3 C2 C7 107.3(4) .
C15 C16 H16 107.9 .
C15 C16 C17 110.9(4) .
C15 C16 C18 111.9(4) .
C17 C16 H16 107.9 .
C18 C16 H16 107.9 .
C18 C16 C17 110.2(4) .
C6A C7A C2A 110.1(4) .
C6A C7A H7AA 109.6 .
C6A C7A H7AB 109.6 .
C2A C7A H7AA 109.6 .
C2A C7A H7AB 109.6 .
H7AA C7A H7AB 108.2 .
H6A C6 H6B 108.1 .
C5 C6 H6A 109.5 .
C5 C6 H6B 109.5 .
C5 C6 C7 110.6(4) .
C7 C6 H6A 109.5 .
C7 C6 H6B 109.5 .
N1 C5 C4 106.3(3) .
N1 C5 C6 106.0(3) .
C8 C5 N1 112.3(3) .
C8 C5 C4 111.9(4) .
C8 C5 C6 113.1(4) .
C6 C5 C4 106.8(4) .
C14 C13 C12 120.7(4) .
C14 C13 H13 119.6 .
C12 C13 H13 119.6 .
C19 C21 H21A 109.5 .
C19 C21 H21B 109.5 .
C19 C21 H21C 109.5 .
H21A C21 H21B 109.5 .
H21A C21 H21C 109.5 .
H21B C21 H21C 109.5 .
C2 C22 H22A 109.5 .
C2 C22 H22B 109.5 .
C2 C22 H22C 109.5 .
H22A C22 H22B 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
C4 C3 H3 106.8 .
C2 C3 C4 110.1(4) .
C2 C3 H3 106.8 .
C9 C3 C4 111.8(4) .
C9 C3 C2 114.2(4) .
C9 C3 H3 106.8 .
C14A C13A C12A 120.5(4) .
C14A C13A H13A 119.8 .
C12A C13A H13A 119.8 .
C19A C20A H20D 109.5 .
C19A C20A H20E 109.5 .
C19A C20A H20F 109.5 .
H20D C20A H20E 109.5 .
H20D C20A H20F 109.5 .
H20E C20A H20F 109.5 .
C2A C22A H22D 109.5 .
C2A C22A H22E 109.5 .
C2A C22A H22F 109.5 .
H22D C22A H22E 109.5 .
H22D C22A H22F 109.5 .
H22E C22A H22F 109.5 .
C2 C7 H7A 109.8 .
C2 C7 H7B 109.8 .
C6 C7 C2 109.4(4) .
C6 C7 H7A 109.8 .
C6 C7 H7B 109.8 .
H7A C7 H7B 108.2 .
C5A C8A H8AA 109.5 .
C5A C8A H8AB 109.5 .
C5A C8A H8AC 109.5 .
H8AA C8A H8AB 109.5 .
H8AA C8A H8AC 109.5 .
H8AB C8A H8AC 109.5 .
C16 C17 H17A 109.5 .
C16 C17 H17B 109.5 .
C16 C17 H17C 109.5 .
H17A C17 H17B 109.5 .
H17A C17 H17C 109.5 .
H17B C17 H17C 109.5 .
C19 C20 H20A 109.5 .
C19 C20 H20B 109.5 .
C19 C20 H20C 109.5 .
H20A C20 H20B 109.5 .
H20A C20 H20C 109.5 .
H20B C20 H20C 109.5 .
C16A C17A H17D 109.5 .
C16A C17A H17E 109.5 .
C16A C17A H17F 109.5 .
H17D C17A H17E 109.5 .
H17D C17A H17F 109.5 .
H17E C17A H17F 109.5 .
C19A C21A H21D 109.5 .
C19A C21A H21E 109.5 .
C19A C21A H21F 109.5 .
H21D C21A H21E 109.5 .
H21D C21A H21F 109.5 .
H21E C21A H21F 109.5 .
C16 C18 H18A 109.5 .
C16 C18 H18B 109.5 .
C16 C18 H18C 109.5 .
H18A C18 H18B 109.5 .
H18A C18 H18C 109.5 .
H18B C18 H18C 109.5 .
C16A C18A H18D 109.5 .
C16A C18A H18E 109.5 .
C16A C18A H18F 109.5 .
H18D C18A H18E 109.5 .
H18D C18A H18F 109.5 .
H18E C18A H18F 109.5 .
C3A C9A H9AA 109.5 .
C3A C9A H9AB 109.5 .
C3A C9A H9AC 109.5 .
H9AA C9A H9AB 109.5 .
H9AA C9A H9AC 109.5 .
H9AB C9A H9AC 109.5 .
C3 C9 H9A 109.5 .
C3 C9 H9B 109.5 .
C3 C9 H9C 109.5 .
H9A C9 H9B 109.5 .
H9A C9 H9C 109.5 .
H9B C9 H9C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br2 Cu2 2.2315(8) .
Br1 Cu2 2.2313(8) .
Cu1 C1 1.919(4) 2_556
Cu1 C1 1.919(4) .
Cu1A C1A 1.945(4) .
Cu1A C1A 1.945(4) 2_667
N1 C10 1.466(5) .
N1 C1 1.306(5) .
N1 C5 1.522(5) .
N1A C1A 1.303(5) .
N1A C10A 1.468(5) .
N1A C5A 1.517(5) .
C10 C11 1.411(6) .
C10 C15 1.394(6) .
C1A C2A 1.518(6) .
C11A C10A 1.385(6) .
C11A C19A 1.529(6) .
C11A C12A 1.389(6) .
C19 H19 1.0000 .
C19 C11 1.512(6) .
C19 C21 1.537(6) .
C19 C20 1.526(6) .
C10A C15A 1.405(6) .
C6A H6AA 0.9900 .
C6A H6AB 0.9900 .
C6A C5A 1.542(6) .
C6A C7A 1.534(6) .
C11 C12 1.408(6) .
C1 C2 1.526(6) .
C2A C3A 1.559(6) .
C2A C7A 1.567(6) .
C2A C22A 1.519(6) .
C4A H4AA 0.9900 .
C4A H4AB 0.9900 .
C4A C5A 1.541(6) .
C4A C3A 1.540(6) .
C14 H14 0.9500 .
C14 C15 1.407(6) .
C14 C13 1.365(7) .
C14A H14A 0.9500 .
C14A C15A 1.413(6) .
C14A C13A 1.356(7) .
C12 H12 0.9500 .
C12 C13 1.376(6) .
C5A C8A 1.518(6) .
C15 C16 1.524(6) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C4 C5 1.542(6) .
C4 C3 1.539(6) .
C3A H3A 1.0000 .
C3A C9A 1.491(7) .
C19A H19A 1.0000 .
C19A C20A 1.534(6) .
C19A C21A 1.534(7) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C8 C5 1.513(6) .
C12A H12A 0.9500 .
C12A C13A 1.396(6) .
C15A C16A 1.513(6) .
C16A H16A 1.0000 .
C16A C17A 1.532(7) .
C16A C18A 1.541(6) .
C2 C22 1.526(6) .
C2 C3 1.536(7) .
C2 C7 1.563(6) .
C16 H16 1.0000 .
C16 C17 1.539(7) .
C16 C18 1.530(6) .
C7A H7AA 0.9900 .
C7A H7AB 0.9900 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C6 C5 1.534(6) .
C6 C7 1.542(6) .
C13 H13 0.9500 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C3 H3 1.0000 .
C3 C9 1.465(8) .
C13A H13A 0.9500 .
C20A H20D 0.9800 .
C20A H20E 0.9800 .
C20A H20F 0.9800 .
C22A H22D 0.9800 .
C22A H22E 0.9800 .
C22A H22F 0.9800 .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8A H8AA 0.9800 .
C8A H8AB 0.9800 .
C8A H8AC 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C17A H17D 0.9800 .
C17A H17E 0.9800 .
C17A H17F 0.9800 .
C21A H21D 0.9800 .
C21A H21E 0.9800 .
C21A H21F 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C18A H18D 0.9800 .
C18A H18E 0.9800 .
C18A H18F 0.9800 .
C9A H9AA 0.9800 .
C9A H9AB 0.9800 .
C9A H9AC 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
