#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/03/4320366.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_4320366
loop_
_publ_author_name
'Seiji Yokota'
'Yoshimitsu Tachi'
'Nagatoshi Nishiwaki'
'Masahiro Ariga'
'Shinobu Itoh'
_publ_section_title
;
 A New β-Diketiminate Ligand Carrying a Functional Group on the Carbon
 Framework. Synthesis and Characterization of a Linear Polymeric Copper(I)
 Complex
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5316
_journal_page_last               5317
_journal_paper_doi               10.1021/ic0155535
_journal_volume                  40
_journal_year                    2001
_chemical_formula_moiety         'C21 H24 Cu N3 O2 '
_chemical_formula_sum            'C21 H24 Cu N3 O2'
_chemical_formula_weight         413.99
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_cell_angle_alpha                90
_cell_angle_beta                 100.0625(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2949(2)
_cell_length_b                   15.7167(5)
_cell_length_c                   16.6267(4)
_cell_measurement_reflns_used    22683
_cell_measurement_temperature    123.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.8
_cell_volume                     1876.96(9)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure Ver. 2.00'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9953
_diffrn_measured_fraction_theta_max 0.9953
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8459
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_exptl_absorpt_coefficient_mu    1.185
_exptl_absorpt_correction_T_max  0.701
_exptl_absorpt_correction_T_min  0.699
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   International_Tables
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.59
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.862
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     268
_refine_ls_number_reflns         3367
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[0.002Fo² + 1.000σ²(Fo)]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0460
_reflns_number_gt                3367
_reflns_number_total             4448
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ic0155535_s2_2.cif
_cod_data_source_block           '_[Cu(2-)]n(3)'
_cod_original_cell_volume        1876.96(8)
_cod_original_formula_sum        'C21 H24 Cu N3 O2 '
_cod_database_code               4320366
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z
x+1/2,-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 -0.10241(3) -0.00847(2) 0.26568(1) 0.01645(7) Uani 1.00 1 d . . .
O1 O 0.6404(2) -0.0252(1) 0.28683(9) 0.0185(4) Uani 1.00 1 d . . .
O2 O 0.5578(2) 0.0557(1) 0.18018(9) 0.0225(4) Uani 1.00 1 d . . .
N1 N 0.1294(2) -0.0515(1) 0.3351(1) 0.0149(4) Uani 1.00 1 d . . .
N2 N 0.0169(2) 0.0445(1) 0.1790(1) 0.0144(4) Uani 1.00 1 d . . .
N3 N 0.5130(2) 0.0140(1) 0.2368(1) 0.0143(4) Uani 1.00 1 d . . .
C1 C 0.3280(3) 0.0075(1) 0.2470(1) 0.0141(4) Uani 1.00 1 d . . .
C2 C 0.2926(3) -0.0388(1) 0.3168(1) 0.0144(4) Uani 1.00 1 d . . .
C3 C 0.1953(3) 0.0453(1) 0.1832(1) 0.0140(4) Uani 1.00 1 d . . .
C4 C 0.1304(2) -0.0999(1) 0.4085(1) 0.0149(4) Uani 1.00 1 d . . .
C5 C 0.0574(3) -0.1824(1) 0.4019(1) 0.0175(5) Uani 1.00 1 d . . .
C6 C 0.0690(3) -0.2308(1) 0.4726(1) 0.0206(5) Uani 1.00 1 d . . .
C7 C 0.1499(3) -0.1998(1) 0.5486(1) 0.0202(5) Uani 1.00 1 d . . .
C8 C 0.2125(3) -0.1160(1) 0.5536(1) 0.0187(5) Uani 1.00 1 d . . .
C9 C 0.2039(3) -0.0642(1) 0.4846(1) 0.0157(4) Uani 1.00 1 d . . .
C10 C -0.0314(3) -0.2173(1) 0.3197(1) 0.0261(5) Uani 1.00 1 d . . .
C11 C 0.1709(3) -0.2560(2) 0.6236(1) 0.0283(6) Uani 1.00 1 d . . .
C12 C 0.2611(3) 0.0282(1) 0.4927(1) 0.0203(5) Uani 1.00 1 d . . .
C13 C -0.0858(2) 0.0837(1) 0.1063(1) 0.0136(4) Uani 1.00 1 d . . .
C14 C -0.0742(3) 0.1718(1) 0.0950(1) 0.0152(4) Uani 1.00 1 d . . .
C15 C -0.1713(3) 0.2062(1) 0.0227(1) 0.0182(5) Uani 1.00 1 d . . .
C16 C -0.2798(3) 0.1569(1) -0.0363(1) 0.0176(5) Uani 1.00 1 d . . .
C17 C -0.2927(3) 0.0699(1) -0.0213(1) 0.0163(5) Uani 1.00 1 d . . .
C18 C -0.1956(3) 0.0321(1) 0.0492(1) 0.0144(4) Uani 1.00 1 d . . .
C19 C 0.0335(3) 0.2282(1) 0.1598(1) 0.0214(5) Uani 1.00 1 d . . .
C20 C -0.3777(3) 0.1950(1) -0.1154(1) 0.0263(6) Uani 1.00 1 d . . .
C21 C -0.2055(3) -0.0625(1) 0.0614(1) 0.0198(5) Uani 1.00 1 d . . .
H1 H 0.3945(3) -0.0649(1) 0.3507(1) 0.017(1) Uiso 1.00 1 c . . .
H2 H 0.2339(3) 0.0748(1) 0.1444(1) 0.017(1) Uiso 1.00 1 c . . .
H3 H 0.0112(3) -0.2863(1) 0.4701(1) 0.025(1) Uiso 1.00 1 c . . .
H4 H 0.2670(3) -0.0971(1) 0.5942(1) 0.023(1) Uiso 1.00 1 c . . .
H5 H 0.0462(3) -0.2149(1) 0.2820(1) 0.031(1) Uiso 1.00 1 c . . .
H6 H -0.1353(3) -0.1826(1) 0.2955(1) 0.031(1) Uiso 1.00 1 c . . .
H7 H -0.0601(3) -0.2679(1) 0.3247(1) 0.031(1) Uiso 1.00 1 c . . .
H8 H 0.2764(3) -0.2946(2) 0.6279(1) 0.034(1) Uiso 1.00 1 c . . .
H9 H 0.0649(3) -0.2924(2) 0.6257(1) 0.034(1) Uiso 1.00 1 c . . .
H10 H 0.2007(3) -0.2235(2) 0.6720(1) 0.034(1) Uiso 1.00 1 c . . .
H11 H 0.3702(3) 0.0415(1) 0.4714(1) 0.024(1) Uiso 1.00 1 c . . .
H12 H 0.2844(3) 0.0457(1) 0.5441(1) 0.025(1) Uiso 1.00 1 c . . .
H13 H 0.1678(3) 0.0694(1) 0.4670(1) 0.024(1) Uiso 1.00 1 c . . .
H14 H -0.1727(3) 0.2651(1) 0.0152(1) 0.022(1) Uiso 1.00 1 c . . .
H15 H -0.3639(3) 0.0407(1) -0.0561(1) 0.019(1) Uiso 1.00 1 c . . .
H16 H 0.1636(3) 0.2185(1) 0.1693(1) 0.025(1) Uiso 1.00 1 c . . .
H17 H 0.0111(3) 0.2831(1) 0.1474(1) 0.025(1) Uiso 1.00 1 c . . .
H18 H -0.0026(3) 0.2197(1) 0.2131(1) 0.026(1) Uiso 1.00 1 c . . .
H19 H -0.3016(3) 0.2005(1) -0.1498(1) 0.031(1) Uiso 1.00 1 c . . .
H20 H -0.4140(3) 0.2477(1) -0.1105(1) 0.032(1) Uiso 1.00 1 c . . .
H21 H -0.4734(3) 0.1630(1) -0.1387(1) 0.031(1) Uiso 1.00 1 c . . .
H22 H -0.0910(3) -0.0923(1) 0.0580(1) 0.024(1) Uiso 1.00 1 c . . .
H23 H -0.2999(3) -0.0869(1) 0.0202(1) 0.024(1) Uiso 1.00 1 c . . .
H24 H -0.2317(3) -0.0801(1) 0.1111(1) 0.024(1) Uiso 1.00 1 c . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.017 0.010
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cu Cu 0.284 1.430
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 . Cu1 . N2 . 97.29(6) yes
Cu1 . N1 . C2 . 122.28(13) yes
Cu1 . N1 . C4 . 123.35(12) yes
C2 . N1 . C4 . 114.36(16) yes
Cu1 . N2 . C3 . 121.97(13) yes
Cu1 . N2 . C13 . 123.77(12) yes
C3 . N2 . C13 . 114.25(15) yes
O1 . N3 . O2 . 119.16(15) yes
O1 . N3 . C1 . 119.31(16) yes
O2 . N3 . C1 . 121.52(16) yes
N3 . C1 . C2 . 116.92(17) yes
N3 . C1 . C3 . 114.94(16) yes
C2 . C1 . C3 . 128.07(17) yes
N1 . C2 . C1 . 124.94(18) yes
N1 . C2 . H1 . 116.94(11) no
C1 . C2 . H1 . 118.02(11) no
N2 . C3 . C1 . 125.37(17) yes
N2 . C3 . H2 . 114.50(11) no
C1 . C3 . H2 . 120.0(1) no
N1 . C4 . C5 . 118.66(17) yes
N1 . C4 . C9 . 119.88(17) yes
C5 . C4 . C9 . 121.46(18) yes
C4 . C5 . C6 . 118.39(18) yes
C4 . C5 . C10 . 120.27(18) yes
C6 . C5 . C10 . 121.34(19) yes
C5 . C6 . C7 . 122.1(2) yes
C5 . C6 . H3 . 119.74(12) no
C7 . C6 . H3 . 118.00(12) no
C6 . C7 . C8 . 118.03(19) yes
C6 . C7 . C11 . 120.7(2) yes
C8 . C7 . C11 . 121.2(2) yes
C7 . C8 . C9 . 122.34(19) yes
C7 . C8 . H4 . 121.68(12) no
C9 . C8 . H4 . 115.47(12) no
C4 . C9 . C8 . 117.50(18) yes
C4 . C9 . C12 . 121.43(18) yes
C8 . C9 . C12 . 120.98(18) yes
C5 . C10 . H5 . 112.75(11) no
C5 . C10 . H6 . 110.83(12) no
H5 . C10 . H6 . 103.070 no
C5 . C10 . H7 . 109.48(12) no
H5 . C10 . H7 . 107.600 no
H6 . C10 . H7 . 112.984 no
C7 . C11 . H8 . 112.89(12) no
C7 . C11 . H9 . 114.16(12) no
H8 . C11 . H9 . 104.825 no
C7 . C11 . H10 . 111.18(13) no
H8 . C11 . H10 . 102.301 no
H9 . C11 . H10 . 110.697 no
C9 . C12 . H11 . 114.6(1) no
C9 . C12 . H12 . 112.83(11) no
H11 . C12 . H12 . 105.016 no
C9 . C12 . H13 . 115.80(11) no
H11 . C12 . H13 . 104.760 no
H12 . C12 . H13 . 102.511 no
N2 . C13 . C14 . 119.94(17) yes
N2 . C13 . C18 . 118.34(17) yes
C14 . C13 . C18 . 121.72(17) yes
C13 . C14 . C15 . 117.75(18) yes
C13 . C14 . C19 . 121.45(18) yes
C15 . C14 . C19 . 120.77(18) yes
C14 . C15 . C16 . 122.36(19) yes
C14 . C15 . H14 . 119.52(12) no
C16 . C15 . H14 . 117.90(12) no
C15 . C16 . C17 . 117.98(18) yes
C15 . C16 . C20 . 121.42(19) yes
C17 . C16 . C20 . 120.59(19) yes
C16 . C17 . C18 . 121.93(19) yes
C16 . C17 . H15 . 117.67(12) no
C18 . C17 . H15 . 120.38(12) no
C13 . C18 . C17 . 118.20(18) yes
C13 . C18 . C21 . 121.29(17) yes
C17 . C18 . C21 . 120.49(18) yes
C14 . C19 . H16 . 113.99(11) no
C14 . C19 . H17 . 110.50(11) no
H16 . C19 . H17 . 109.370 no
C14 . C19 . H18 . 112.23(11) no
H16 . C19 . H18 . 104.349 no
H17 . C19 . H18 . 105.933 no
C16 . C20 . H19 . 110.76(11) no
C16 . C20 . H20 . 113.52(12) no
H19 . C20 . H20 . 101.823 no
C16 . C20 . H21 . 111.72(12) no
H19 . C20 . H21 . 108.257 no
H20 . C20 . H21 . 110.241 no
C18 . C21 . H22 . 114.1(1) no
C18 . C21 . H23 . 109.98(11) no
H22 . C21 . H23 . 106.472 no
C18 . C21 . H24 . 116.14(11) no
H22 . C21 . H24 . 102.907 no
H23 . C21 . H24 . 106.488 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 . N1 . 1.9916(16) yes
Cu1 . N2 . 1.9911(16) yes
O1 . N3 . 1.290(2) yes
O2 . N3 . 1.237(2) yes
N1 . C2 . 1.295(2) yes
N1 . C4 . 1.438(2) yes
N2 . C3 . 1.291(2) yes
N2 . C13 . 1.445(2) yes
N3 . C1 . 1.393(2) yes
C1 . C2 . 1.430(3) yes
C1 . C3 . 1.435(3) yes
C2 . H1 . 0.945 no
C3 . H2 . 0.879 no
C4 . C5 . 1.399(3) yes
C4 . C9 . 1.403(3) yes
C5 . C6 . 1.390(3) yes
C5 . C10 . 1.509(3) yes
C6 . C7 . 1.387(3) yes
C6 . H3 . 0.966 no
C7 . C8 . 1.392(3) yes
C7 . C11 . 1.513(3) yes
C8 . C9 . 1.400(3) yes
C8 . H4 . 0.780 no
C9 . C12 . 1.510(3) yes
C10 . H5 . 0.917 no
C10 . H6 . 0.962 no
C10 . H7 . 0.831 no
C11 . H8 . 0.973 no
C11 . H9 . 0.967 no
C11 . H10 . 0.946 no
C12 . H11 . 0.949 no
C12 . H12 . 0.886 no
C12 . H13 . 0.982 no
C13 . C14 . 1.402(3) yes
C13 . C18 . 1.392(3) yes
C14 . C15 . 1.394(3) yes
C14 . C19 . 1.506(3) yes
C15 . C16 . 1.385(3) yes
C15 . H14 . 0.933 no
C16 . C17 . 1.396(3) yes
C16 . C20 . 1.506(3) yes
C17 . C18 . 1.392(3) yes
C17 . H15 . 0.843 no
C18 . C21 . 1.504(3) yes
C19 . H16 . 0.947 no
C19 . H17 . 0.895 no
C19 . H18 . 0.976 no
C20 . H19 . 0.868 no
C20 . H20 . 0.877 no
C20 . H21 . 0.892 no
C21 . H22 . 0.968 no
C21 . H23 . 0.962 no
C21 . H24 . 0.922 no
loop_
_geom_contact_atom_site_label_1
_geom_contact_site_symmetry_1
_geom_contact_atom_site_label_2
_geom_contact_site_symmetry_2
_geom_contact_distance
_geom_contact_publ_flag
Cu1 . O1 1_455 1.9860(14) yes
Cu1 . O2 1_455 2.8195(15) yes
Cu1 . N1 . 1.9916(16) yes
Cu1 . N2 . 1.9911(16) yes
Cu1 . N3 1_455 2.7849(17) yes
Cu1 . C1 . 3.2186(19) yes
Cu1 . C2 . 2.8978(19) yes
Cu1 . C3 . 2.8905(18) yes
Cu1 . C4 . 3.0300(19) yes
Cu1 . C10 . 3.418(2) yes
Cu1 . C13 . 3.0411(18) yes
Cu1 . C21 . 3.453(2) yes
Cu1 . H4 2_556 3.255(2) no
Cu1 . H5 . 3.417(2) no
Cu1 . H6 . 2.799(2) no
Cu1 . H24 . 2.813(2) no
O1 . O2 . 2.179(2) yes
O1 . N1 1_655 3.541(2) yes
O1 . N3 . 1.290(2) yes
O1 . C1 . 2.316(2) yes
O1 . C2 . 2.678(2) yes
O1 . C3 . 3.575(2) yes
O1 . C8 2_656 3.481(3) yes
O1 . H1 . 2.323(2) no
O1 . H4 2_656 2.755(3) no
O1 . H6 1_655 2.956(3) no
O1 . H12 2_656 2.787(3) no
O1 . H21 2_555 3.346(3) no
O1 . H24 1_655 3.333(2) no
O2 . N2 1_655 3.357(2) yes
O2 . N3 . 1.237(2) yes
O2 . C1 . 2.296(2) yes
O2 . C2 . 3.556(2) yes
O2 . C3 . 2.659(2) yes
O2 . C13 1_655 3.095(2) yes
O2 . C17 2_555 3.582(3) yes
O2 . C18 1_655 3.080(2) yes
O2 . C19 4_555 3.414(3) yes
O2 . C21 1_655 3.395(3) yes
O2 . H2 . 2.353(2) no
O2 . H15 2_555 2.745(3) no
O2 . H17 4_555 2.602(3) no
O2 . H21 2_555 3.539(3) no
O2 . H23 2_555 3.563(3) no
O2 . H24 1_655 2.975(3) no
N1 . N2 . 2.989(2) yes
N1 . C1 . 2.417(2) yes
N1 . C2 . 1.295(2) yes
N1 . C3 . 3.058(2) yes
N1 . C4 . 1.438(2) yes
N1 . C5 . 2.439(3) yes
N1 . C9 . 2.458(3) yes
N1 . C10 . 2.850(3) yes
N1 . C12 . 2.912(3) yes
N1 . H1 . 1.918(2) no
N1 . H5 . 2.749(3) no
N1 . H6 . 2.822(3) no
N1 . H11 . 2.995(3) no
N1 . H13 . 2.877(3) no
N2 . C1 . 2.423(2) yes
N2 . C2 . 3.065(2) yes
N2 . C3 . 1.291(2) yes
N2 . C13 . 1.445(2) yes
N2 . C14 . 2.464(3) yes
N2 . C18 . 2.436(2) yes
N2 . C19 . 2.910(3) yes
N2 . C21 . 2.859(3) yes
N2 . H2 . 1.839(2) no
N2 . H16 . 2.951(3) no
N2 . H18 . 2.819(3) no
N2 . H22 . 2.956(3) no
N2 . H24 . 2.772(3) no
N3 . C1 . 1.393(2) yes
N3 . C2 . 2.406(3) yes
N3 . C3 . 2.384(3) yes
N3 . H1 . 2.539(3) no
N3 . H2 . 2.515(3) no
N3 . H4 2_656 3.256(3) no
N3 . H15 2_555 3.132(3) no
N3 . H17 4_555 3.517(3) no
N3 . H21 2_555 3.213(3) no
N3 . H24 1_655 3.374(3) no
C1 . C2 . 1.430(3) yes
C1 . C3 . 1.435(3) yes
C1 . H1 . 2.051(3) no
C1 . H2 . 2.023(3) no
C1 . H15 2_555 3.319(3) no
C1 . H21 2_555 3.496(3) no
C2 . C3 . 2.576(3) yes
C2 . C4 . 2.298(3) yes
C2 . C5 . 3.301(3) yes
C2 . C9 . 2.999(3) yes
C2 . C12 . 3.154(3) yes
C2 . H1 . 0.945 no
C2 . H2 . 3.340(3) no
C2 . H5 . 3.296(3) no
C2 . H7 4_545 3.218(3) no
C2 . H11 . 2.831(3) no
C2 . H12 2_656 3.520(3) no
C2 . H13 . 3.279(3) no
C3 . C13 . 2.299(3) yes
C3 . C14 . 2.993(3) yes
C3 . C17 2_555 3.420(3) yes
C3 . C18 . 3.305(3) yes
C3 . C19 . 3.106(3) yes
C3 . H1 . 3.384(3) no
C3 . H2 . 0.879 no
C3 . H15 2_555 2.952(3) no
C3 . H16 . 2.737(3) no
C3 . H18 . 3.176(3) no
C3 . H22 . 3.443(3) no
C4 . C5 . 1.399(3) yes
C4 . C6 . 2.395(3) yes
C4 . C7 . 2.793(3) yes
C4 . C8 . 2.396(3) yes
C4 . C9 . 1.403(3) yes
C4 . C10 . 2.522(3) yes
C4 . C12 . 2.541(3) yes
C4 . H1 . 2.363(2) no
C4 . H3 . 3.271(3) no
C4 . H3 4_545 3.311(3) no
C4 . H4 . 3.075(3) no
C4 . H5 . 2.760(3) no
C4 . H6 . 2.775(3) no
C4 . H7 . 3.188(3) no
C4 . H7 4_545 3.529(3) no
C4 . H11 . 2.909(3) no
C4 . H12 . 3.271(3) no
C4 . H12 2_556 3.367(3) no
C4 . H13 . 2.830(3) no
C4 . H13 2_556 3.290(3) no
C5 . C6 . 1.390(3) yes
C5 . C7 . 2.430(3) yes
C5 . C8 . 2.781(3) yes
C5 . C9 . 2.444(3) yes
C5 . C10 . 1.509(3) yes
C5 . H1 . 3.304(3) no
C5 . H3 . 2.049(3) no
C5 . H3 4_545 3.343(3) no
C5 . H4 . 3.557(3) no
C5 . H5 . 2.047(3) no
C5 . H6 . 2.058(3) no
C5 . H7 . 1.951(3) no
C5 . H7 4_545 3.361(3) no
C5 . H12 2_556 3.525(3) no
C5 . H13 2_556 3.444(3) no
C6 . C7 . 1.387(3) yes
C6 . C8 . 2.382(3) yes
C6 . C9 . 2.793(3) yes
C6 . C10 . 2.528(3) yes
C6 . C11 . 2.521(3) yes
C6 . H3 . 0.966 no
C6 . H3 4_545 3.2449(4) no
C6 . H4 . 3.094(3) no
C6 . H5 . 3.155(3) no
C6 . H6 . 3.151(3) no
C6 . H7 . 2.543(3) no
C6 . H8 . 2.931(3) no
C6 . H9 . 2.728(3) no
C6 . H10 . 3.289(3) no
C6 . H13 2_556 3.322(3) no
C7 . C8 . 1.392(3) yes
C7 . C9 . 2.445(3) yes
C7 . C11 . 1.513(3) yes
C7 . H3 . 2.029(3) no
C7 . H3 4_545 3.146(3) no
C7 . H4 . 1.920(3) no
C7 . H8 . 2.093(3) no
C7 . H8 4_445 3.228(3) no
C7 . H9 . 2.103(3) no
C7 . H9 4_545 3.077(3) no
C7 . H10 . 2.054(3) no
C7 . H13 2_556 3.071(3) no
C8 . C9 . 1.400(3) yes
C8 . C11 . 2.531(3) yes
C8 . C12 . 2.532(3) yes
C8 . H3 . 3.246(3) no
C8 . H3 4_545 3.176(3) no
C8 . H4 . 0.780 no
C8 . H8 . 3.069(3) no
C8 . H9 . 3.276(3) no
C8 . H9 4_545 3.007(3) no
C8 . H10 . 2.607(3) no
C8 . H11 . 3.142(3) no
C8 . H11 2_656 3.354(3) no
C8 . H12 . 2.606(3) no
C8 . H13 . 3.241(3) no
C8 . H13 2_556 2.832(3) no
C9 . C12 . 1.510(3) yes
C9 . C12 2_556 3.524(3) yes
C9 . H1 . 2.824(3) no
C9 . H3 4_545 3.285(3) no
C9 . H4 . 1.873(3) no
C9 . H11 . 2.092(3) no
C9 . H11 2_656 3.085(3) no
C9 . H12 . 2.025(3) no
C9 . H12 2_556 3.522(3) no
C9 . H13 . 2.129(3) no
C9 . H13 2_556 2.961(3) no
C10 . H1 4_445 3.518(3) no
C10 . H3 . 2.694(3) no
C10 . H5 . 0.917 no
C10 . H5 4_445 3.2170(15) no
C10 . H6 . 0.962 no
C10 . H6 4_545 3.376(2) no
C10 . H7 . 0.831 no
C10 . H7 4_545 3.4329(3) no
C10 . H19 3_445 3.151(3) no
C10 . H20 3_445 3.475(3) no
C10 . H21 3_445 3.556(3) no
C11 . H3 . 2.656(3) no
C11 . H4 . 2.662(3) no
C11 . H8 . 0.973 no
C11 . H8 4_445 2.9980(13) no
C11 . H9 . 0.967 no
C11 . H9 4_545 2.9672(13) no
C11 . H10 . 0.946 no
C11 . H11 3_546 3.542(3) no
C11 . H13 3_546 3.436(3) no
C11 . H16 3_546 3.467(3) no
C11 . H18 2_556 3.221(3) no
C11 . H18 3_546 3.329(3) no
C12 . C12 2_656 3.563(4) yes
C12 . H1 . 3.076(3) no
C12 . H1 2_656 3.338(3) no
C12 . H3 3_556 3.359(3) no
C12 . H4 . 2.588(3) no
C12 . H8 3_556 3.414(3) no
C12 . H11 . 0.949 no
C12 . H11 2_656 2.869(4) no
C12 . H12 . 0.886 no
C12 . H13 . 0.982 no
C13 . C14 . 1.402(3) yes
C13 . C15 . 2.393(3) yes
C13 . C16 . 2.789(3) yes
C13 . C17 . 2.389(3) yes
C13 . C18 . 1.392(3) yes
C13 . C19 . 2.537(3) yes
C13 . C21 . 2.525(3) yes
C13 . H2 . 2.311(3) no
C13 . H14 . 3.239(3) no
C13 . H15 . 3.154(3) no
C13 . H16 . 2.868(3) no
C13 . H17 . 3.258(3) no
C13 . H18 . 2.777(3) no
C13 . H22 . 2.879(3) no
C13 . H22 2_555 3.221(3) no
C13 . H23 . 3.301(3) no
C13 . H24 . 2.793(3) no
C14 . C15 . 1.394(3) yes
C14 . C16 . 2.435(3) yes
C14 . C17 . 2.787(3) yes
C14 . C18 . 2.440(3) yes
C14 . C19 . 1.506(3) yes
C14 . C19 4_455 3.591(3) yes
C14 . H2 . 2.721(3) no
C14 . H14 . 2.024(3) no
C14 . H14 4_555 3.561(3) no
C14 . H16 . 2.080(3) no
C14 . H16 4_455 2.997(3) no
C14 . H17 . 2.004(3) no
C14 . H17 4_455 3.367(3) no
C14 . H18 . 2.082(3) no
C14 . H22 2_555 3.249(3) no
C15 . C16 . 1.385(3) yes
C15 . C17 . 2.384(3) yes
C15 . C18 . 2.783(3) yes
C15 . C19 . 2.522(3) yes
C15 . C19 4_455 3.551(3) yes
C15 . C20 . 2.523(3) yes
C15 . H14 . 0.933 no
C15 . H15 . 3.133(3) no
C15 . H16 . 3.141(3) no
C15 . H16 4_455 3.133(3) no
C15 . H17 . 2.562(3) no
C15 . H17 4_455 3.372(3) no
C15 . H18 . 3.197(3) no
C15 . H19 . 2.862(3) no
C15 . H20 . 2.664(3) no
C15 . H20 4_555 3.227(3) no
C15 . H21 . 3.233(3) no
C15 . H22 2_555 3.093(3) no
C15 . H23 3_455 3.328(3) no
C16 . C17 . 1.396(3) yes
C16 . C18 . 2.438(3) yes
C16 . C20 . 1.506(3) yes
C16 . H14 . 2.000(3) no
C16 . H14 4_455 3.363(3) no
C16 . H15 . 1.937(3) no
C16 . H19 . 1.988(3) no
C16 . H20 . 2.023(3) no
C16 . H20 4_555 3.470(3) no
C16 . H21 . 2.015(3) no
C16 . H22 2_555 2.969(3) no
C16 . H23 2_455 3.313(3) no
C17 . C18 . 1.392(3) yes
C17 . C20 . 2.522(3) yes
C17 . C21 . 2.515(3) yes
C17 . H2 2_555 3.140(3) no
C17 . H14 . 3.219(3) no
C17 . H15 . 0.843 no
C17 . H15 2_455 3.475(4) no
C17 . H19 . 2.956(3) no
C17 . H20 . 3.214(3) no
C17 . H21 . 2.605(3) no
C17 . H22 . 3.119(3) no
C17 . H22 2_555 2.988(3) no
C17 . H23 . 2.562(3) no
C17 . H23 2_455 2.986(3) no
C17 . H24 . 3.204(3) no
C17 . H24 2_455 3.533(3) no
C18 . C21 . 1.504(3) yes
C18 . H2 . 3.323(3) no
C18 . H2 2_555 3.598(3) no
C18 . H15 . 1.958(3) no
C18 . H15 2_455 3.432(3) no
C18 . H22 . 2.094(3) no
C18 . H22 2_555 3.122(3) no
C18 . H23 . 2.043(3) no
C18 . H24 . 2.082(3) no
C19 . H2 . 2.853(3) no
C19 . H8 3_556 3.578(3) no
C19 . H10 2_556 3.523(3) no
C19 . H10 3_556 3.203(3) no
C19 . H14 . 2.668(3) no
C19 . H14 4_555 3.491(3) no
C19 . H16 . 0.947 no
C19 . H16 4_455 2.8562(12) no
C19 . H17 . 0.895 no
C19 . H17 4_555 3.5301(2) no
C19 . H18 . 0.976 no
C19 . H18 4_555 3.444(1) no
C20 . H5 3_455 3.161(3) no
C20 . H6 3_455 3.574(3) no
C20 . H7 3_455 3.478(3) no
C20 . H14 . 2.651(3) no
C20 . H14 4_455 3.372(3) no
C20 . H15 . 2.614(3) no
C20 . H19 . 0.868 no
C20 . H19 4_455 3.459(2) no
C20 . H20 . 0.877 no
C20 . H20 4_555 3.4880(12) no
C20 . H21 . 0.892 no
C20 . H22 3_455 3.495(3) no
C20 . H23 2_455 3.496(3) no
C20 . H24 2_455 3.385(3) no
C21 . H2 2_555 3.399(3) no
C21 . H14 3_445 3.059(3) no
C21 . H15 . 2.644(3) no
C21 . H15 2_455 3.146(3) no
C21 . H20 3_445 3.175(3) no
C21 . H21 2_455 3.268(3) no
C21 . H22 . 0.968 no
C21 . H23 . 0.962 no
C21 . H24 . 0.922 no
H1 . H3 4_545 3.090(3) no
H1 . H4 2_656 3.553(3) no
H1 . H5 . 3.508(3) no
H1 . H7 4_545 2.693(3) no
H1 . H11 . 2.642(3) no
H1 . H11 2_656 3.171(3) no
H1 . H12 2_656 2.685(3) no
H1 . H13 . 3.470(3) no
H2 . H14 4_555 3.453(3) no
H2 . H15 2_555 2.615(3) no
H2 . H16 . 2.367(3) no
H2 . H17 4_555 3.007(3) no
H2 . H18 . 3.185(3) no
H2 . H22 2_555 3.357(3) no
H2 . H23 2_555 2.868(3) no
H3 . H4 4_445 3.475(3) no
H3 . H5 . 3.375(3) no
H3 . H6 . 3.338(3) no
H3 . H7 . 2.401(3) no
H3 . H8 . 2.978(3) no
H3 . H9 . 2.550(3) no
H3 . H10 . 3.540(3) no
H3 . H11 3_546 2.953(3) no
H3 . H12 3_546 3.061(3) no
H3 . H13 3_546 3.297(3) no
H4 . H8 . 3.153(3) no
H4 . H9 . 3.484(3) no
H4 . H9 4_545 2.760(3) no
H4 . H10 . 2.465(3) no
H4 . H11 . 3.165(3) no
H4 . H11 2_656 3.156(3) no
H4 . H12 . 2.404(3) no
H4 . H13 . 3.362(3) no
H4 . H13 2_556 3.187(3) no
H5 . H6 . 1.472 no
H5 . H6 4_545 2.804(3) no
H5 . H7 . 1.411 no
H5 . H7 4_545 2.8485(4) no
H5 . H19 2_555 3.127(3) no
H5 . H19 3_445 2.899(3) no
H5 . H20 3_445 2.905(3) no
H5 . H21 3_445 3.033(3) no
H6 . H7 . 1.497 no
H6 . H7 4_445 3.3119(11) no
H6 . H19 3_445 3.011(3) no
H6 . H20 3_445 3.343(3) no
H6 . H21 2_455 3.527(3) no
H6 . H24 . 3.426(3) no
H7 . H19 3_445 2.948(3) no
H7 . H20 3_445 3.541(3) no
H7 . H21 3_445 3.327(3) no
H8 . H9 . 1.538 no
H8 . H9 4_545 2.514(3) no
H8 . H10 . 1.495 no
H8 . H10 4_545 3.0664(5) no
H8 . H11 3_546 3.144(3) no
H8 . H13 3_546 2.729(3) no
H8 . H16 3_546 3.330(3) no
H8 . H18 3_546 2.870(3) no
H9 . H10 . 1.574 no
H9 . H10 4_445 2.9031(4) no
H9 . H11 3_546 3.149(3) no
H9 . H13 3_546 3.457(3) no
H9 . H18 2_556 3.020(3) no
H10 . H16 3_546 2.803(3) no
H10 . H17 3_546 3.353(3) no
H10 . H18 2_556 2.590(3) no
H10 . H18 3_546 2.798(3) no
H11 . H11 2_656 2.359(4) no
H11 . H12 . 1.457 no
H11 . H12 2_656 2.919(4) no
H11 . H13 . 1.530 no
H12 . H13 . 1.458 no
H13 . H13 2_556 3.590(4) no
H14 . H16 . 3.306(3) no
H14 . H16 4_455 3.022(3) no
H14 . H17 . 2.383(3) no
H14 . H17 4_455 3.536(3) no
H14 . H18 . 3.384(3) no
H14 . H19 . 2.922(3) no
H14 . H20 . 2.501(3) no
H14 . H20 4_555 3.058(3) no
H14 . H21 . 3.460(3) no
H14 . H21 4_555 3.351(3) no
H14 . H22 3_455 2.956(3) no
H14 . H23 3_455 2.400(3) no
H14 . H24 3_455 3.209(3) no
H15 . H15 2_455 3.217(4) no
H15 . H19 . 3.033(3) no
H15 . H20 . 3.380(3) no
H15 . H21 . 2.416(3) no
H15 . H22 . 3.257(3) no
H15 . H22 2_555 3.422(3) no
H15 . H23 . 2.374(3) no
H15 . H23 2_455 2.722(3) no
H15 . H24 . 3.365(3) no
H15 . H24 2_455 2.998(3) no
H16 . H17 . 1.503 no
H16 . H17 4_555 2.62312(8) no
H16 . H18 . 1.519 no
H16 . H18 4_555 2.6049(16) no
H17 . H18 . 1.495 no
H17 . H18 4_555 3.52530(11) no
H17 . H23 3_455 3.580(3) no
H19 . H20 . 1.355 no
H19 . H20 4_555 2.9053(13) no
H19 . H21 . 1.427 no
H19 . H21 4_555 3.195(3) no
H19 . H22 2_555 3.449(3) no
H19 . H24 3_455 3.508(3) no
H20 . H21 . 1.451 no
H20 . H22 3_455 2.661(3) no
H20 . H23 3_455 3.261(3) no
H20 . H24 3_455 2.908(3) no
H21 . H23 2_455 3.030(3) no
H21 . H24 2_455 2.622(3) no
H22 . H23 . 1.546 no
H22 . H24 . 1.478 no
H23 . H24 . 1.510 no
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_site_symmetry_1
_geom_torsion_atom_site_label_2
_geom_torsion_site_symmetry_2
_geom_torsion_atom_site_label_3
_geom_torsion_site_symmetry_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N2 . Cu1 . N1 . C2 . 1.3(3) yes
N2 . Cu1 . N1 . C4 . -177.8(3) yes
N1 . Cu1 . N2 . C3 . -2.6(3) yes
N1 . Cu1 . N2 . C13 . 176.4(3) yes
Cu1 . N1 . C2 . C1 . 0.9(3) yes
C4 . N1 . C2 . C1 . -179.9(2) yes
Cu1 . N1 . C4 . C5 . 68.6(2) yes
Cu1 . N1 . C4 . C9 . -111.4(2) yes
C2 . N1 . C4 . C5 . -110.5(3) yes
C2 . N1 . C4 . C9 . 69.5(3) yes
Cu1 . N2 . C3 . C1 . 1.9(3) yes
C13 . N2 . C3 . C1 . -177.2(2) yes
Cu1 . N2 . C13 . C14 . 112.6(2) yes
Cu1 . N2 . C13 . C18 . -67.0(2) yes
C3 . N2 . C13 . C14 . -68.3(3) yes
C3 . N2 . C13 . C18 . 112.1(3) yes
O1 . N3 . C1 . C2 . 3.9(3) yes
O1 . N3 . C1 . C3 . -173.3(2) yes
O2 . N3 . C1 . C2 . -177.0(2) yes
O2 . N3 . C1 . C3 . 5.8(3) yes
N3 . C1 . C2 . N1 . -179.4(2) yes
C3 . C1 . C2 . N1 . -2.7(4) yes
N3 . C1 . C3 . N2 . 177.8(2) yes
C2 . C1 . C3 . N2 . 1.0(5) yes
N1 . C4 . C5 . C6 . 176.2(2) yes
N1 . C4 . C5 . C10 . -3.8(4) yes
C9 . C4 . C5 . C6 . -3.8(4) yes
C9 . C4 . C5 . C10 . 176.2(2) yes
N1 . C4 . C9 . C8 . -175.9(2) yes
N1 . C4 . C9 . C12 . 7.6(4) yes
C5 . C4 . C9 . C8 . 4.0(4) yes
C5 . C4 . C9 . C12 . -172.5(2) yes
C4 . C5 . C6 . C7 . 0.1(4) yes
C10 . C5 . C6 . C7 . -179.9(3) yes
C5 . C6 . C7 . C8 . 3.2(4) yes
C5 . C6 . C7 . C11 . -176.2(3) yes
C6 . C7 . C8 . C9 . -2.9(4) yes
C11 . C7 . C8 . C9 . 176.5(3) yes
C7 . C8 . C9 . C4 . -0.6(4) yes
C7 . C8 . C9 . C12 . 175.9(3) yes
N2 . C13 . C14 . C15 . 178.1(2) yes
N2 . C13 . C14 . C19 . -4.1(4) yes
C18 . C13 . C14 . C15 . -2.4(4) yes
C18 . C13 . C14 . C19 . 175.4(2) yes
N2 . C13 . C18 . C17 . -179.3(2) yes
N2 . C13 . C18 . C21 . -1.1(4) yes
C14 . C13 . C18 . C17 . 1.2(4) yes
C14 . C13 . C18 . C21 . 179.3(2) yes
C13 . C14 . C15 . C16 . 1.3(4) yes
C19 . C14 . C15 . C16 . -176.5(3) yes
C14 . C15 . C16 . C17 . 1.0(4) yes
C14 . C15 . C16 . C20 . -177.7(3) yes
C15 . C16 . C17 . C18 . -2.3(4) yes
C20 . C16 . C17 . C18 . 176.4(3) yes
C16 . C17 . C18 . C13 . 1.2(4) yes
C16 . C17 . C18 . C21 . -177.0(2) yes
