#------------------------------------------------------------------------------
#$Date: 2017-02-17 08:57:54 +0200 (Fri, 17 Feb 2017) $
#$Revision: 192220 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/70/7117072.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_7117072
loop_
_publ_author_name
'Koichi Tanaka'
'Tomoharu Iwashita'
'Erika Yoshida'
'Tomomi Ishikawa'
'Shinya Otuka'
'Zofia Urbanczyk-Lipkowska'
'Hiroki Takahashi'
_publ_section_title
;
 Solvent-dependent strong asymmetric amplification in the catalytic
 enantioselective Henry reaction using the
 trans-N,N'-bis-biphenyl-4-ylmethyl-cyclohexane-1,2-diamine-CuCl2 complex
;
_journal_name_full               Chem.Commun.
_journal_page_first              7907
_journal_paper_doi               10.1039/C5cc02302E
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_formula_sum            'C36 H42 Cl2 Cu N2 O2'
_chemical_formula_weight         669.15
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-01-05 deposited with the CCDC.
2015-04-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.0460(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8568(3)
_cell_length_b                   15.8847(4)
_cell_length_c                   15.2073(4)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      67.88
_cell_measurement_theta_min      4.04
_cell_volume                     3328.68(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0363
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35306
_diffrn_reflns_theta_full        67.55
_diffrn_reflns_theta_max         67.55
_diffrn_reflns_theta_min         4.04
_exptl_absorpt_coefficient_mu    2.664
_exptl_absorpt_correction_T_max  0.4627
_exptl_absorpt_correction_T_min  0.2045
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1404
_exptl_crystal_size_max          0.87
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.34
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.059(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     795
_refine_ls_number_reflns         9740
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0270
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0388P)²+0.8642P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0697
_reflns_number_gt                9703
_reflns_number_total             9740
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc02302e2.cif
_cod_data_source_block           tana_1_12_b_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 3105 2015-03-04 15:46:00Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7117072
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu -0.201858(18) 0.273165(17) -0.000666(17) 0.01509(8) Uani 1 1 d . . .
Cu2 Cu 0.697799(19) 0.072386(17) 1.003697(18) 0.01519(8) Uani 1 1 d . . .
Cl1 Cl -0.33584(3) 0.33180(3) -0.07735(3) 0.01947(11) Uani 1 1 d . . .
Cl2 Cl -0.28623(3) 0.22241(3) 0.10754(3) 0.01917(11) Uani 1 1 d . . .
Cl3 Cl 0.83058(3) 0.01646(3) 1.08145(3) 0.02053(11) Uani 1 1 d . . .
Cl4 Cl 0.78145(3) 0.12360(3) 0.89455(3) 0.01967(11) Uani 1 1 d . . .
O1 O 0.67934(13) 0.02441(16) 0.26391(11) 0.0395(5) Uani 1 1 d . . .
O2 O 0.70783(14) 0.11972(14) 0.37139(11) 0.0380(4) Uani 1 1 d . . .
O3 O 0.78264(15) 0.21275(14) 0.62666(12) 0.0406(5) Uani 1 1 d . . .
O4 O 0.81737(15) 0.31128(15) 0.73032(11) 0.0399(5) Uani 1 1 d . . .
N1 N -0.07186(12) 0.22166(15) 0.05485(12) 0.0160(4) Uani 1 1 d . . .
N2 N -0.11859(12) 0.33450(13) -0.08026(11) 0.0161(4) Uani 1 1 d . . .
N3 N 0.57179(12) 0.12735(13) 0.95109(11) 0.0155(4) Uani 1 1 d . . .
N4 N 0.60955(12) 0.00043(12) 1.07080(11) 0.0152(4) Uani 1 1 d . . .
C1 C 0.00762(14) 0.24529(14) 0.00077(13) 0.0157(4) Uani 1 1 d . . .
H1 H 0.0458 0.2921 0.0316 0.019 Uiso 1 1 calc R . .
C2 C 0.07719(14) 0.17293(15) -0.01331(14) 0.0209(4) Uani 1 1 d . . .
H2C H 0.0403 0.1253 -0.0423 0.025 Uiso 1 1 calc R . .
H2D H 0.1081 0.1532 0.0447 0.025 Uiso 1 1 calc R . .
C3 C 0.15567(17) 0.20100(18) -0.07070(16) 0.0277(5) Uani 1 1 d . . .
H3C H 0.1979 0.2432 -0.0379 0.033 Uiso 1 1 calc R . .
H3D H 0.1964 0.1520 -0.0826 0.033 Uiso 1 1 calc R . .
C4 C 0.11256(15) 0.23893(17) -0.15845(14) 0.0290(5) Uani 1 1 d . . .
H4C H 0.0769 0.1949 -0.1948 0.035 Uiso 1 1 calc R . .
H4D H 0.1654 0.2602 -0.1914 0.035 Uiso 1 1 calc R . .
C5 C 0.04335(15) 0.31124(17) -0.14211(14) 0.0220(5) Uani 1 1 d . . .
H5A H 0.0794 0.3570 -0.1088 0.026 Uiso 1 1 calc R . .
H5B H 0.0139 0.3344 -0.1992 0.026 Uiso 1 1 calc R . .
C6 C -0.03555(13) 0.27707(13) -0.08926(12) 0.0159(4) Uani 1 1 d . . .
H6 H -0.0632 0.2266 -0.1222 0.019 Uiso 1 1 calc R . .
C7 C -0.09682(15) 0.42408(14) -0.05642(13) 0.0192(4) Uani 1 1 d . . .
H7A H -0.1506 0.4597 -0.0835 0.023 Uiso 1 1 calc R . .
H7B H -0.0371 0.4411 -0.0823 0.023 Uiso 1 1 calc R . .
C8 C -0.08298(15) 0.44123(14) 0.04231(14) 0.0177(4) Uani 1 1 d . . .
C9 C 0.00888(15) 0.45943(15) 0.08536(14) 0.0206(4) Uani 1 1 d . . .
H9 H 0.0639 0.4591 0.0530 0.025 Uiso 1 1 calc R . .
C10 C 0.02023(15) 0.47795(15) 0.17522(15) 0.0221(5) Uani 1 1 d . . .
H10 H 0.0833 0.4897 0.2034 0.027 Uiso 1 1 calc R . .
C11 C -0.05861(16) 0.47970(15) 0.22479(14) 0.0213(5) Uani 1 1 d . . .
C12 C -0.15021(15) 0.46171(17) 0.18090(15) 0.0231(5) Uani 1 1 d . . .
H12 H -0.2054 0.4620 0.2131 0.028 Uiso 1 1 calc R . .
C13 C -0.16183(16) 0.44344(16) 0.09097(15) 0.0211(5) Uani 1 1 d . . .
H13 H -0.2249 0.4323 0.0625 0.025 Uiso 1 1 calc R . .
C14 C -0.04727(16) 0.50185(16) 0.32002(14) 0.0236(5) Uani 1 1 d . . .
C15 C -0.11375(17) 0.47443(18) 0.37700(16) 0.0277(5) Uani 1 1 d . . .
H15 H -0.1660 0.4391 0.3548 0.033 Uiso 1 1 calc R . .
C16 C -0.10465(19) 0.4980(2) 0.46552(16) 0.0331(6) Uani 1 1 d . . .
H16 H -0.1510 0.4794 0.5030 0.040 Uiso 1 1 calc R . .
C17 C -0.0283(2) 0.54863(19) 0.49922(16) 0.0360(6) Uani 1 1 d . . .
H17 H -0.0223 0.5649 0.5597 0.043 Uiso 1 1 calc R . .
C18 C 0.0391(2) 0.5754(2) 0.44449(16) 0.0368(6) Uani 1 1 d . . .
H18 H 0.0923 0.6093 0.4677 0.044 Uiso 1 1 calc R . .
C19 C 0.02937(18) 0.55292(18) 0.35550(15) 0.0307(5) Uani 1 1 d . . .
H19 H 0.0755 0.5726 0.3183 0.037 Uiso 1 1 calc R . .
C20 C -0.04967(14) 0.24037(15) 0.15103(13) 0.0194(4) Uani 1 1 d . . .
H20A H -0.1081 0.2275 0.1808 0.023 Uiso 1 1 calc R . .
H20B H -0.0371 0.3015 0.1578 0.023 Uiso 1 1 calc R . .
C21 C 0.03544(15) 0.19353(15) 0.19864(13) 0.0186(5) Uani 1 1 d . . .
C22 C 0.12107(15) 0.23599(17) 0.22796(15) 0.0228(5) Uani 1 1 d . . .
H22 H 0.1279 0.2938 0.2137 0.027 Uiso 1 1 calc R . .
C23 C 0.19693(16) 0.19427(16) 0.27803(15) 0.0239(5) Uani 1 1 d . . .
H23 H 0.2548 0.2241 0.2970 0.029 Uiso 1 1 calc R . .
C24 C 0.18901(16) 0.11038(16) 0.30030(13) 0.0194(4) Uani 1 1 d . . .
C25 C 0.10420(15) 0.06788(17) 0.26856(13) 0.0230(5) Uani 1 1 d . . .
H25 H 0.0980 0.0097 0.2813 0.028 Uiso 1 1 calc R . .
C26 C 0.02915(16) 0.10889(16) 0.21895(14) 0.0234(5) Uani 1 1 d . . .
H26 H -0.0278 0.0784 0.1984 0.028 Uiso 1 1 calc R . .
C27 C 0.26390(15) 0.06708(17) 0.36207(13) 0.0205(5) Uani 1 1 d . . .
C28 C 0.27978(18) -0.01915(17) 0.35579(17) 0.0267(5) Uani 1 1 d . . .
H28 H 0.2490 -0.0497 0.3069 0.032 Uiso 1 1 calc R . .
C29 C 0.34012(18) -0.06096(19) 0.42026(17) 0.0330(6) Uani 1 1 d . . .
H29 H 0.3503 -0.1198 0.4153 0.040 Uiso 1 1 calc R . .
C30 C 0.38589(18) -0.0168(2) 0.49234(17) 0.0320(6) Uani 1 1 d . . .
H30 H 0.4245 -0.0458 0.5381 0.038 Uiso 1 1 calc R . .
C31 C 0.37438(17) 0.0693(2) 0.49640(16) 0.0309(6) Uani 1 1 d . . .
H31 H 0.4077 0.1003 0.5437 0.037 Uiso 1 1 calc R . .
C32 C 0.31432(16) 0.11083(17) 0.43167(15) 0.0245(5) Uani 1 1 d . . .
H32 H 0.3075 0.1702 0.4349 0.029 Uiso 1 1 calc R . .
C33 C 0.50748(13) 0.12177(14) 1.02344(12) 0.0160(4) Uani 1 1 d . . .
H33 H 0.5383 0.1569 1.0733 0.019 Uiso 1 1 calc R . .
C34 C 0.50752(13) 0.03145(13) 1.05692(12) 0.0158(4) Uani 1 1 d . . .
H34 H 0.4709 -0.0042 1.0105 0.019 Uiso 1 1 calc R . .
C35 C 0.61788(15) -0.09205(15) 1.05596(13) 0.0191(4) Uani 1 1 d . . .
H35A H 0.5686 -0.1219 1.0869 0.023 Uiso 1 1 calc R . .
H35B H 0.6828 -0.1116 1.0813 0.023 Uiso 1 1 calc R . .
C36 C 0.60349(15) -0.11324(14) 0.95877(14) 0.0177(4) Uani 1 1 d . . .
C37 C 0.67933(15) -0.10472(15) 0.90584(15) 0.0203(5) Uani 1 1 d . . .
H37 H 0.7416 -0.0875 0.9318 0.024 Uiso 1 1 calc R . .
C38 C 0.66488(15) -0.12117(16) 0.81551(14) 0.0214(5) Uani 1 1 d . . .
H38 H 0.7175 -0.1150 0.7807 0.026 Uiso 1 1 calc R . .
C39 C 0.57432(15) -0.14665(14) 0.77505(14) 0.0193(4) Uani 1 1 d . . .
C40 C 0.49923(15) -0.15586(14) 0.82872(14) 0.0207(4) Uani 1 1 d . . .
H40 H 0.4371 -0.1736 0.8030 0.025 Uiso 1 1 calc R . .
C41 C 0.51336(15) -0.13976(14) 0.91865(14) 0.0201(4) Uani 1 1 d . . .
H41 H 0.4610 -0.1469 0.9535 0.024 Uiso 1 1 calc R . .
C42 C 0.55998(15) -0.16759(16) 0.67829(14) 0.0219(4) Uani 1 1 d . . .
C43 C 0.62164(16) -0.13587(17) 0.62005(15) 0.0256(5) Uani 1 1 d . . .
H43 H 0.6724 -0.0986 0.6413 0.031 Uiso 1 1 calc R . .
C44 C 0.61025(19) -0.1579(2) 0.53086(16) 0.0321(6) Uani 1 1 d . . .
H44 H 0.6548 -0.1375 0.4925 0.039 Uiso 1 1 calc R . .
C45 C 0.53435(19) -0.2093(2) 0.49808(16) 0.0344(6) Uani 1 1 d . . .
H45 H 0.5254 -0.2232 0.4370 0.041 Uiso 1 1 calc R . .
C46 C 0.4720(2) -0.24013(19) 0.55509(16) 0.0349(6) Uani 1 1 d . . .
H46 H 0.4195 -0.2754 0.5330 0.042 Uiso 1 1 calc R . .
C47 C 0.48481(17) -0.22026(18) 0.64444(15) 0.0289(5) Uani 1 1 d . . .
H47 H 0.4417 -0.2429 0.6830 0.035 Uiso 1 1 calc R . .
C48 C 0.45622(15) 0.02651(16) 1.14104(14) 0.0207(5) Uani 1 1 d . . .
H48A H 0.4543 -0.0327 1.1610 0.025 Uiso 1 1 calc R . .
H48B H 0.4929 0.0597 1.1885 0.025 Uiso 1 1 calc R . .
C49 C 0.35310(14) 0.06066(15) 1.12405(14) 0.0244(5) Uani 1 1 d . . .
H49A H 0.3146 0.0241 1.0808 0.029 Uiso 1 1 calc R . .
H49B H 0.3221 0.0599 1.1798 0.029 Uiso 1 1 calc R . .
C50 C 0.35339(15) 0.14995(16) 1.08858(14) 0.0220(5) Uani 1 1 d . . .
H50A H 0.3880 0.1873 1.1335 0.026 Uiso 1 1 calc R . .
H50B H 0.2858 0.1704 1.0767 0.026 Uiso 1 1 calc R . .
C51 C 0.40302(14) 0.15338(15) 1.00342(14) 0.0192(4) Uani 1 1 d . . .
H51A H 0.4031 0.2119 0.9810 0.023 Uiso 1 1 calc R . .
H51B H 0.3675 0.1176 0.9575 0.023 Uiso 1 1 calc R . .
C52 C 0.53577(14) 0.08949(15) 0.86427(13) 0.0180(4) Uani 1 1 d . . .
H52A H 0.5109 0.0324 0.8752 0.022 Uiso 1 1 calc R . .
H52B H 0.5917 0.0828 0.8294 0.022 Uiso 1 1 calc R . .
C53 C 0.45681(15) 0.13750(15) 0.80820(13) 0.0180(4) Uani 1 1 d . . .
C54 C 0.37391(15) 0.09616(16) 0.77165(15) 0.0230(5) Uani 1 1 d . . .
H54 H 0.3658 0.0381 0.7838 0.028 Uiso 1 1 calc R . .
C55 C 0.30278(16) 0.13810(16) 0.71771(15) 0.0221(5) Uani 1 1 d . . .
H55 H 0.2469 0.1082 0.6934 0.027 Uiso 1 1 calc R . .
C56 C 0.31160(15) 0.22328(16) 0.69845(13) 0.0184(4) Uani 1 1 d . . .
C57 C 0.39514(15) 0.26515(16) 0.73613(14) 0.0227(5) Uani 1 1 d . . .
H57 H 0.4029 0.3235 0.7249 0.027 Uiso 1 1 calc R . .
C58 C 0.46687(16) 0.22252(17) 0.78972(14) 0.0230(5) Uani 1 1 d . . .
H58 H 0.5233 0.2519 0.8139 0.028 Uiso 1 1 calc R . .
C59 C 0.23881(15) 0.26856(17) 0.63767(14) 0.0211(5) Uani 1 1 d . . .
C60 C 0.18881(16) 0.22632(18) 0.56579(14) 0.0247(5) Uani 1 1 d . . .
H60 H 0.1959 0.1672 0.5599 0.030 Uiso 1 1 calc R . .
C61 C 0.12839(17) 0.2713(2) 0.50256(16) 0.0299(5) Uani 1 1 d . . .
H61 H 0.0965 0.2427 0.4529 0.036 Uiso 1 1 calc R . .
C62 C 0.11486(19) 0.3562(2) 0.51170(17) 0.0341(6) Uani 1 1 d . . .
H62 H 0.0745 0.3863 0.4681 0.041 Uiso 1 1 calc R . .
C63 C 0.16012(19) 0.39785(19) 0.58448(18) 0.0339(6) Uani 1 1 d . . .
H63 H 0.1495 0.4564 0.5916 0.041 Uiso 1 1 calc R . .
C64 C 0.22120(18) 0.35451(18) 0.64739(17) 0.0279(5) Uani 1 1 d . . .
H64 H 0.2513 0.3837 0.6975 0.034 Uiso 1 1 calc R . .
C65 C 0.65792(18) 0.05725(19) 0.33044(16) 0.0309(6) Uani 1 1 d . . .
C66 C 0.7940(2) 0.1480(2) 0.3325(2) 0.0462(8) Uani 1 1 d . . .
H66A H 0.7823 0.1462 0.2672 0.055 Uiso 1 1 calc R . .
H66B H 0.8496 0.1107 0.3515 0.055 Uiso 1 1 calc R . .
C67 C 0.8157(3) 0.2344(3) 0.3622(3) 0.0729(12) Uani 1 1 d . . .
H67A H 0.7697 0.2732 0.3299 0.109 Uiso 1 1 calc R . .
H67B H 0.8819 0.2491 0.3508 0.109 Uiso 1 1 calc R . .
H67C H 0.8099 0.2387 0.4257 0.109 Uiso 1 1 calc R . .
C68 C 0.5722(2) 0.0329(2) 0.37676(18) 0.0424(7) Uani 1 1 d . . .
H68A H 0.5276 0.0807 0.3769 0.064 Uiso 1 1 calc R . .
H68B H 0.5941 0.0167 0.4378 0.064 Uiso 1 1 calc R . .
H68C H 0.5388 -0.0147 0.3459 0.064 Uiso 1 1 calc R . .
C69 C 0.6677(3) 0.1034(3) 0.6367(3) 0.0694(12) Uani 1 1 d . . .
H69A H 0.6608 0.1025 0.5719 0.104 Uiso 1 1 calc R . .
H69B H 0.6056 0.0887 0.6581 0.104 Uiso 1 1 calc R . .
H69C H 0.7172 0.0626 0.6594 0.104 Uiso 1 1 calc R . .
C70 C 0.6973(2) 0.1890(2) 0.66824(18) 0.0433(7) Uani 1 1 d . . .
H70A H 0.6441 0.2296 0.6523 0.052 Uiso 1 1 calc R . .
H70B H 0.7121 0.1890 0.7334 0.052 Uiso 1 1 calc R . .
C71 C 0.83648(19) 0.2753(2) 0.66477(16) 0.0321(6) Uani 1 1 d . . .
C72 C 0.9217(2) 0.2960(2) 0.6157(2) 0.0504(8) Uani 1 1 d . . .
H72A H 0.9416 0.3543 0.6280 0.076 Uiso 1 1 calc R . .
H72B H 0.9036 0.2889 0.5521 0.076 Uiso 1 1 calc R . .
H72C H 0.9757 0.2581 0.6350 0.076 Uiso 1 1 calc R . .
H1N H -0.0816(17) 0.176(2) 0.0475(16) 0.012(7) Uiso 1 1 d . . .
H3N H 0.5869(16) 0.1812(19) 0.9431(15) 0.012(6) Uiso 1 1 d . . .
H2N H -0.1551(17) 0.3371(18) -0.1302(17) 0.021(6) Uiso 1 1 d . . .
H4N H 0.6308(15) 0.0105(15) 1.1246(15) 0.007(5) Uiso 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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
N2 Cu1 N1 84.68(7) . .
N2 Cu1 Cl2 169.44(6) . .
N1 Cu1 Cl2 93.24(5) . .
N2 Cu1 Cl1 88.98(5) . .
N1 Cu1 Cl1 172.93(5) . .
Cl2 Cu1 Cl1 93.558(19) . .
N4 Cu2 N3 84.37(7) . .
N4 Cu2 Cl3 90.92(5) . .
N3 Cu2 Cl3 171.63(5) . .
N4 Cu2 Cl4 161.97(6) . .
N3 Cu2 Cl4 92.39(5) . .
Cl3 Cu2 Cl4 94.19(2) . .
C65 O2 C66 116.7(2) . .
C71 O3 C70 116.6(2) . .
C1 N1 C20 113.75(16) . .
C1 N1 Cu1 109.66(13) . .
C20 N1 Cu1 113.61(14) . .
C1 N1 H1N 107(2) . .
C20 N1 H1N 111(2) . .
Cu1 N1 H1N 100.8(19) . .
C6 N2 C7 117.99(16) . .
C6 N2 Cu1 104.90(13) . .
C7 N2 Cu1 115.49(13) . .
C6 N2 H2N 109.5(17) . .
C7 N2 H2N 104.6(19) . .
Cu1 N2 H2N 103.4(17) . .
C52 N3 C33 117.41(16) . .
C52 N3 Cu2 111.61(13) . .
C33 N3 Cu2 103.82(12) . .
C52 N3 H3N 109.2(15) . .
C33 N3 H3N 108.9(15) . .
Cu2 N3 H3N 105.1(15) . .
C34 N4 C35 113.02(16) . .
C34 N4 Cu2 110.85(13) . .
C35 N4 Cu2 114.75(13) . .
C34 N4 H4N 107.4(14) . .
C35 N4 H4N 107.7(16) . .
Cu2 N4 H4N 102.2(15) . .
N1 C1 C6 109.68(15) . .
N1 C1 C2 113.65(18) . .
C6 C1 C2 108.49(17) . .
N1 C1 H1 108.3 . .
C6 C1 H1 108.3 . .
C2 C1 H1 108.3 . .
C1 C2 C3 110.92(19) . .
C1 C2 H2C 109.5 . .
C3 C2 H2C 109.5 . .
C1 C2 H2D 109.5 . .
C3 C2 H2D 109.5 . .
H2C C2 H2D 108.0 . .
C4 C3 C2 112.16(18) . .
C4 C3 H3C 109.2 . .
C2 C3 H3C 109.2 . .
C4 C3 H3D 109.2 . .
C2 C3 H3D 109.2 . .
H3C C3 H3D 107.9 . .
C3 C4 C5 110.34(19) . .
C3 C4 H4C 109.6 . .
C5 C4 H4C 109.6 . .
C3 C4 H4D 109.6 . .
C5 C4 H4D 109.6 . .
H4C C4 H4D 108.1 . .
C6 C5 C4 108.3(2) . .
C6 C5 H5A 110.0 . .
C4 C5 H5A 110.0 . .
C6 C5 H5B 110.0 . .
C4 C5 H5B 110.0 . .
H5A C5 H5B 108.4 . .
N2 C6 C1 110.84(15) . .
N2 C6 C5 115.82(18) . .
C1 C6 C5 110.92(15) . .
N2 C6 H6 106.2 . .
C1 C6 H6 106.2 . .
C5 C6 H6 106.2 . .
N2 C7 C8 114.39(18) . .
N2 C7 H7A 108.7 . .
C8 C7 H7A 108.7 . .
N2 C7 H7B 108.7 . .
C8 C7 H7B 108.7 . .
H7A C7 H7B 107.6 . .
C13 C8 C9 118.4(2) . .
C13 C8 C7 120.60(19) . .
C9 C8 C7 120.92(19) . .
C10 C9 C8 120.4(2) . .
C10 C9 H9 119.8 . .
C8 C9 H9 119.8 . .
C9 C10 C11 121.52(19) . .
C9 C10 H10 119.2 . .
C11 C10 H10 119.2 . .
C10 C11 C12 117.5(2) . .
C10 C11 C14 121.7(2) . .
C12 C11 C14 120.8(2) . .
C13 C12 C11 121.1(2) . .
C13 C12 H12 119.4 . .
C11 C12 H12 119.4 . .
C8 C13 C12 121.0(2) . .
C8 C13 H13 119.5 . .
C12 C13 H13 119.5 . .
C19 C14 C15 117.7(2) . .
C19 C14 C11 120.8(2) . .
C15 C14 C11 121.5(2) . .
C16 C15 C14 121.2(2) . .
C16 C15 H15 119.4 . .
C14 C15 H15 119.4 . .
C17 C16 C15 120.2(2) . .
C17 C16 H16 119.9 . .
C15 C16 H16 119.9 . .
C18 C17 C16 119.7(2) . .
C18 C17 H17 120.2 . .
C16 C17 H17 120.2 . .
C17 C18 C19 120.2(3) . .
C17 C18 H18 119.9 . .
C19 C18 H18 119.9 . .
C18 C19 C14 121.1(2) . .
C18 C19 H19 119.5 . .
C14 C19 H19 119.5 . .
N1 C20 C21 116.16(18) . .
N1 C20 H20A 108.2 . .
C21 C20 H20A 108.2 . .
N1 C20 H20B 108.2 . .
C21 C20 H20B 108.2 . .
H20A C20 H20B 107.4 . .
C26 C21 C22 118.0(2) . .
C26 C21 C20 121.4(2) . .
C22 C21 C20 120.6(2) . .
C21 C22 C23 120.6(2) . .
C21 C22 H22 119.7 . .
C23 C22 H22 119.7 . .
C24 C23 C22 121.1(2) . .
C24 C23 H23 119.5 . .
C22 C23 H23 119.5 . .
C23 C24 C25 117.8(2) . .
C23 C24 C27 122.1(2) . .
C25 C24 C27 119.9(2) . .
C26 C25 C24 121.2(2) . .
C26 C25 H25 119.4 . .
C24 C25 H25 119.4 . .
C25 C26 C21 121.2(2) . .
C25 C26 H26 119.4 . .
C21 C26 H26 119.4 . .
C32 C27 C28 118.2(2) . .
C32 C27 C24 120.6(2) . .
C28 C27 C24 121.0(2) . .
C29 C28 C27 120.7(2) . .
C29 C28 H28 119.7 . .
C27 C28 H28 119.7 . .
C28 C29 C30 120.3(3) . .
C28 C29 H29 119.9 . .
C30 C29 H29 119.9 . .
C31 C30 C29 119.2(2) . .
C31 C30 H30 120.4 . .
C29 C30 H30 120.4 . .
C30 C31 C32 120.2(3) . .
C30 C31 H31 119.9 . .
C32 C31 H31 119.9 . .
C31 C32 C27 121.2(3) . .
C31 C32 H32 119.4 . .
C27 C32 H32 119.4 . .
N3 C33 C34 108.90(16) . .
N3 C33 C51 117.38(15) . .
C34 C33 C51 110.03(16) . .
N3 C33 H33 106.7 . .
C34 C33 H33 106.7 . .
C51 C33 H33 106.7 . .
N4 C34 C33 109.01(16) . .
N4 C34 C48 112.46(15) . .
C33 C34 C48 110.13(17) . .
N4 C34 H34 108.4 . .
C33 C34 H34 108.4 . .
C48 C34 H34 108.4 . .
N4 C35 C36 111.30(18) . .
N4 C35 H35A 109.4 . .
C36 C35 H35A 109.4 . .
N4 C35 H35B 109.4 . .
C36 C35 H35B 109.4 . .
H35A C35 H35B 108.0 . .
C37 C36 C41 118.06(19) . .
C37 C36 C35 120.90(19) . .
C41 C36 C35 121.02(19) . .
C38 C37 C36 120.8(2) . .
C38 C37 H37 119.6 . .
C36 C37 H37 119.6 . .
C37 C38 C39 121.2(2) . .
C37 C38 H38 119.4 . .
C39 C38 H38 119.4 . .
C40 C39 C38 117.56(19) . .
C40 C39 C42 121.32(19) . .
C38 C39 C42 121.04(19) . .
C41 C40 C39 121.43(19) . .
C41 C40 H40 119.3 . .
C39 C40 H40 119.3 . .
C40 C41 C36 120.94(19) . .
C40 C41 H41 119.5 . .
C36 C41 H41 119.5 . .
C43 C42 C47 118.0(2) . .
C43 C42 C39 121.2(2) . .
C47 C42 C39 120.8(2) . .
C42 C43 C44 121.0(2) . .
C42 C43 H43 119.5 . .
C44 C43 H43 119.5 . .
C45 C44 C43 120.2(2) . .
C45 C44 H44 119.9 . .
C43 C44 H44 119.9 . .
C46 C45 C44 119.1(2) . .
C46 C45 H45 120.4 . .
C44 C45 H45 120.4 . .
C45 C46 C47 120.8(3) . .
C45 C46 H46 119.6 . .
C47 C46 H46 119.6 . .
C46 C47 C42 120.8(2) . .
C46 C47 H47 119.6 . .
C42 C47 H47 119.6 . .
C49 C48 C34 110.48(17) . .
C49 C48 H48A 109.6 . .
C34 C48 H48A 109.6 . .
C49 C48 H48B 109.6 . .
C34 C48 H48B 109.6 . .
H48A C48 H48B 108.1 . .
C50 C49 C48 110.80(18) . .
C50 C49 H49A 109.5 . .
C48 C49 H49A 109.5 . .
C50 C49 H49B 109.5 . .
C48 C49 H49B 109.5 . .
H49A C49 H49B 108.1 . .
C49 C50 C51 110.64(19) . .
C49 C50 H50A 109.5 . .
C51 C50 H50A 109.5 . .
C49 C50 H50B 109.5 . .
C51 C50 H50B 109.5 . .
H50A C50 H50B 108.1 . .
C50 C51 C33 108.64(17) . .
C50 C51 H51A 110.0 . .
C33 C51 H51A 110.0 . .
C50 C51 H51B 110.0 . .
C33 C51 H51B 110.0 . .
H51A C51 H51B 108.3 . .
N3 C52 C53 116.70(18) . .
N3 C52 H52A 108.1 . .
C53 C52 H52A 108.1 . .
N3 C52 H52B 108.1 . .
C53 C52 H52B 108.1 . .
H52A C52 H52B 107.3 . .
C54 C53 C58 118.4(2) . .
C54 C53 C52 120.3(2) . .
C58 C53 C52 121.3(2) . .
C55 C54 C53 121.1(2) . .
C55 C54 H54 119.4 . .
C53 C54 H54 119.4 . .
C54 C55 C56 121.3(2) . .
C54 C55 H55 119.4 . .
C56 C55 H55 119.4 . .
C55 C56 C57 117.5(2) . .
C55 C56 C59 122.3(2) . .
C57 C56 C59 120.2(2) . .
C58 C57 C56 121.0(2) . .
C58 C57 H57 119.5 . .
C56 C57 H57 119.5 . .
C53 C58 C57 120.7(2) . .
C53 C58 H58 119.7 . .
C57 C58 H58 119.7 . .
C64 C59 C60 118.2(2) . .
C64 C59 C56 121.6(2) . .
C60 C59 C56 120.2(2) . .
C59 C60 C61 120.1(3) . .
C59 C60 H60 120.0 . .
C61 C60 H60 120.0 . .
C62 C61 C60 120.7(3) . .
C62 C61 H61 119.7 . .
C60 C61 H61 119.7 . .
C61 C62 C63 119.8(2) . .
C61 C62 H62 120.1 . .
C63 C62 H62 120.1 . .
C62 C63 C64 120.4(3) . .
C62 C63 H63 119.8 . .
C64 C63 H63 119.8 . .
C63 C64 C59 120.7(2) . .
C63 C64 H64 119.6 . .
C59 C64 H64 119.6 . .
O1 C65 O2 123.8(3) . .
O1 C65 C68 124.3(3) . .
O2 C65 C68 111.9(2) . .
O2 C66 C67 108.3(3) . .
O2 C66 H66A 110.0 . .
C67 C66 H66A 110.0 . .
O2 C66 H66B 110.0 . .
C67 C66 H66B 110.0 . .
H66A C66 H66B 108.4 . .
C66 C67 H67A 109.5 . .
C66 C67 H67B 109.5 . .
H67A C67 H67B 109.5 . .
C66 C67 H67C 109.5 . .
H67A C67 H67C 109.5 . .
H67B C67 H67C 109.5 . .
C65 C68 H68A 109.5 . .
C65 C68 H68B 109.5 . .
H68A C68 H68B 109.5 . .
C65 C68 H68C 109.5 . .
H68A C68 H68C 109.5 . .
H68B C68 H68C 109.5 . .
C70 C69 H69A 109.5 . .
C70 C69 H69B 109.5 . .
H69A C69 H69B 109.5 . .
C70 C69 H69C 109.5 . .
H69A C69 H69C 109.5 . .
H69B C69 H69C 109.5 . .
O3 C70 C69 107.9(3) . .
O3 C70 H70A 110.1 . .
C69 C70 H70A 110.1 . .
O3 C70 H70B 110.1 . .
C69 C70 H70B 110.1 . .
H70A C70 H70B 108.4 . .
O4 C71 O3 123.4(3) . .
O4 C71 C72 124.3(3) . .
O3 C71 C72 112.3(2) . .
C71 C72 H72A 109.5 . .
C71 C72 H72B 109.5 . .
H72A C72 H72B 109.5 . .
C71 C72 H72C 109.5 . .
H72A C72 H72C 109.5 . .
H72B C72 H72C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N2 2.0099(18) .
Cu1 N1 2.0753(18) .
Cu1 Cl2 2.2649(5) .
Cu1 Cl1 2.2844(5) .
Cu2 N4 2.0263(18) .
Cu2 N3 2.0388(17) .
Cu2 Cl3 2.2615(5) .
Cu2 Cl4 2.2729(5) .
O1 C65 1.203(3) .
O2 C65 1.327(4) .
O2 C66 1.458(4) .
O3 C71 1.338(4) .
O3 C70 1.448(3) .
O4 C71 1.202(3) .
N1 C1 1.490(3) .
N1 C20 1.492(3) .
N1 H1N 0.74(3) .
N2 C6 1.486(3) .
N2 C7 1.491(3) .
N2 H2N 0.87(3) .
N3 C52 1.488(3) .
N3 C33 1.490(3) .
N3 H3N 0.89(3) .
N4 C34 1.491(2) .
N4 C35 1.493(3) .
N4 H4N 0.86(2) .
C1 C6 1.521(3) .
C1 C2 1.530(3) .
C1 H1 1.0000 .
C2 C3 1.531(3) .
C2 H2C 0.9900 .
C2 H2D 0.9900 .
C3 C4 1.527(3) .
C3 H3C 0.9900 .
C3 H3D 0.9900 .
C4 C5 1.533(3) .
C4 H4C 0.9900 .
C4 H4D 0.9900 .
C5 C6 1.523(3) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 H6 1.0000 .
C7 C8 1.518(3) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C13 1.383(3) .
C8 C9 1.399(3) .
C9 C10 1.390(3) .
C9 H9 0.9500 .
C10 C11 1.391(3) .
C10 H10 0.9500 .
C11 C12 1.400(3) .
C11 C14 1.483(3) .
C12 C13 1.391(3) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 C19 1.399(3) .
C14 C15 1.399(4) .
C15 C16 1.390(4) .
C15 H15 0.9500 .
C16 C17 1.383(4) .
C16 H16 0.9500 .
C17 C18 1.383(4) .
C17 H17 0.9500 .
C18 C19 1.392(3) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C20 C21 1.513(3) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 C26 1.384(4) .
C21 C22 1.397(3) .
C22 C23 1.398(3) .
C22 H22 0.9500 .
C23 C24 1.382(4) .
C23 H23 0.9500 .
C24 C25 1.397(3) .
C24 C27 1.492(3) .
C25 C26 1.382(3) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C27 C32 1.391(3) .
C27 C28 1.392(4) .
C28 C29 1.389(4) .
C28 H28 0.9500 .
C29 C30 1.396(4) .
C29 H29 0.9500 .
C30 C31 1.380(5) .
C30 H30 0.9500 .
C31 C32 1.387(4) .
C31 H31 0.9500 .
C32 H32 0.9500 .
C33 C34 1.522(3) .
C33 C51 1.532(3) .
C33 H33 1.0000 .
C34 C48 1.529(3) .
C34 H34 1.0000 .
C35 C36 1.509(3) .
C35 H35A 0.9900 .
C35 H35B 0.9900 .
C36 C37 1.396(3) .
C36 C41 1.396(3) .
C37 C38 1.392(3) .
C37 H37 0.9500 .
C38 C39 1.398(3) .
C38 H38 0.9500 .
C39 C40 1.396(3) .
C39 C42 1.501(3) .
C40 C41 1.385(3) .
C40 H40 0.9500 .
C41 H41 0.9500 .
C42 C43 1.388(3) .
C42 C47 1.392(3) .
C43 C44 1.393(4) .
C43 H43 0.9500 .
C44 C45 1.383(4) .
C44 H44 0.9500 .
C45 C46 1.377(4) .
C45 H45 0.9500 .
C46 C47 1.388(3) .
C46 H46 0.9500 .
C47 H47 0.9500 .
C48 C49 1.525(3) .
C48 H48A 0.9900 .
C48 H48B 0.9900 .
C49 C50 1.518(4) .
C49 H49A 0.9900 .
C49 H49B 0.9900 .
C50 C51 1.530(3) .
C50 H50A 0.9900 .
C50 H50B 0.9900 .
C51 H51A 0.9900 .
C51 H51B 0.9900 .
C52 C53 1.520(3) .
C52 H52A 0.9900 .
C52 H52B 0.9900 .
C53 C54 1.387(3) .
C53 C58 1.389(4) .
C54 C55 1.385(3) .
C54 H54 0.9500 .
C55 C56 1.392(4) .
C55 H55 0.9500 .
C56 C57 1.404(3) .
C56 C59 1.481(3) .
C57 C58 1.393(3) .
C57 H57 0.9500 .
C58 H58 0.9500 .
C59 C64 1.398(4) .
C59 C60 1.402(3) .
C60 C61 1.403(3) .
C60 H60 0.9500 .
C61 C62 1.370(5) .
C61 H61 0.9500 .
C62 C63 1.382(4) .
C62 H62 0.9500 .
C63 C64 1.391(4) .
C63 H63 0.9500 .
C64 H64 0.9500 .
C65 C68 1.494(4) .
C66 C67 1.465(6) .
C66 H66A 0.9900 .
C66 H66B 0.9900 .
C67 H67A 0.9800 .
C67 H67B 0.9800 .
C67 H67C 0.9800 .
C68 H68A 0.9800 .
C68 H68B 0.9800 .
C68 H68C 0.9800 .
C69 C70 1.484(6) .
C69 H69A 0.9800 .
C69 H69B 0.9800 .
C69 H69C 0.9800 .
C70 H70A 0.9900 .
C70 H70B 0.9900 .
C71 C72 1.498(4) .
C72 H72A 0.9800 .
C72 H72B 0.9800 .
C72 H72C 0.9800 .
