#------------------------------------------------------------------------------
#$Date: 2019-11-10 19:10:22 +0200 (Sun, 10 Nov 2019) $
#$Revision: 226002 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/59/4515923.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_4515923
loop_
_publ_author_name
'Hossain, Anowar'
'Dey, Arka'
'Seth, Saikat Kumar'
'Ray, Partha Pratim'
'Ballester, Pablo'
'Pritchard, Robin G.'
'Ortega-Castro, Joaquín'
'Frontera, Antonio'
'Mukhopadhyay, Subrata'
_publ_section_title
;
 Enhanced Photosensitive Schottky Diode Behavior of Pyrazine over
 2-Aminopyrimidine Ligand in Copper(II)-Phthalate MOFs: Experimental and
 Theoretical Rationalization.
;
_journal_issue                   8
_journal_name_full               'ACS omega'
_journal_page_first              9160
_journal_page_last               9171
_journal_paper_doi               10.1021/acsomega.8b01111
_journal_volume                  3
_journal_year                    2018
_chemical_formula_moiety         'C40 H30 Cu2 N6 O16, 2(H2 O)'
_chemical_formula_sum            'C40 H34 Cu2 N6 O18'
_chemical_formula_weight         1013.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-06-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.253(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.8505(5)
_cell_length_b                   10.4670(4)
_cell_length_c                   18.8893(9)
_cell_measurement_reflns_used    2604
_cell_measurement_temperature    150.03(10)
_cell_measurement_theta_max      26.6090
_cell_measurement_theta_min      3.8420
_cell_volume                     2069.73(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.03(10)
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   20.00   84.00   1.0000    1.0650
omega____ theta____ kappa____ phi______ frames
    -       18.8601   57.0000  -60.0000 64

#__ type_ start__ end____ width___ exp.time_
  2 omega   13.00   72.00   1.0000    1.0650
omega____ theta____ kappa____ phi______ frames
    -       18.8601   37.0000  -90.0000 59

#__ type_ start__ end____ width___ exp.time_
  3 omega  -48.00   11.00   1.0000    1.0650
omega____ theta____ kappa____ phi______ frames
    -       18.8601    0.0000  -60.0000 59

#__ type_ start__ end____ width___ exp.time_
  4 omega  -70.00  -30.00   1.0000    1.0650
omega____ theta____ kappa____ phi______ frames
    -      -17.7663  135.0000   90.0000 40
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0798
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9115
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         3.856
_exptl_absorpt_coefficient_mu    1.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93439
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_description       block
_exptl_crystal_F_000             1036
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         4572
_refine_ls_number_restraints     357
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0524
_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)+(0.0357P)²+1.6827P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1221
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3310
_reflns_number_total             4572
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao8b01111_si_003.cif
_cod_data_source_block           argp1017sai
_cod_original_cell_volume        2069.73(16)
_cod_database_code               4515923
_shelx_shelxl_version_number     2018/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.946
_shelx_estimated_absorpt_t_min   0.791
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 C14A-C13A \\sim C9-C14 \\sim C14-C13 \\sim C13-C12 \\sim C13A-C12A \\sim
C12A-C11A \\sim C12-C11 ~
 C11A-C10A \\sim C11-C10 \\sim C9-C10
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C14 \\sim C14A \\sim C9 \\sim C13 \\sim C13A \\sim C12 \\sim C12A \\sim C11
\\sim C11A \\sim C10A \\sim C10: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01
O7 \\sim O8 \\sim C16 \\sim O8A \\sim C16A \\sim O7A: within 2A with sigma of
0.04 and sigma for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 O7, O8, C16, O8A, C16A, O7A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C14, C14A, C9, C13, C13A, C12, C12A, C11, C11A, C10A, C10
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O7A)=Sof(C16A)=Sof(O8A)=Sof(H8A)=Sof(O9A)=Sof(H9AA)=Sof(H9AB)=Sof(C10A)=
 Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=
 Sof(H14A)=1-FVAR(1)
 Sof(C10)=Sof(C11)=Sof(H11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=Sof(C14)=
 Sof(H14)=Sof(O9)=Sof(H9A)=Sof(H9B)=Sof(C16)=Sof(O8)=Sof(H8)=Sof(O7)=FVAR(1)
6.a Free rotating group:
 O9(H9A,H9B), O9A(H9AA,H9AB)
6.b Rotating group:
 N3(H3A,H3B)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4A), C5(H5), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14),
 C18(H18), C19(H19), C20(H20), C11A(H11A), C12A(H12A), C13A(H13A), C14A(H14A)
6.d Fitted hexagon refined as free rotating group:
 C9(C10,C11,C12,C13,C14)
6.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O8(H8), O8A(H8A)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.02380(4) 0.37467(4) 0.49715(2) 0.02105(14) Uani 1 1 d . . . . .
O1 O 1.0309(2) 0.4049(2) 0.39540(13) 0.0225(5) Uani 1 1 d . . . . .
O2 O 0.9983(2) 0.6169(2) 0.40272(14) 0.0261(6) Uani 1 1 d . . . . .
O3 O 1.0030(3) 0.8553(2) 0.30627(14) 0.0322(6) Uani 1 1 d . . . . .
O4 O 1.1886(2) 0.7923(2) 0.38183(13) 0.0253(6) Uani 1 1 d . . . . .
H4 H 1.174527 0.851704 0.408534 0.038 Uiso 1 1 calc GR . . . .
N1 N 1.1115(3) 0.1835(3) 0.51177(15) 0.0209(6) Uani 1 1 d . . . . .
N2 N 1.1707(3) -0.0219(3) 0.47567(16) 0.0239(7) Uani 1 1 d . . . . .
N3 N 1.0418(3) 0.1141(3) 0.39179(17) 0.0381(9) Uani 1 1 d . . . . .
H3A H 1.057673 0.053538 0.364210 0.046 Uiso 1 1 d GR . . . .
H3B H 1.063668 0.185928 0.375691 0.046 Uiso 1 1 d GR . . . .
C1 C 1.0605(3) 0.5382(3) 0.30059(19) 0.0220(8) Uani 1 1 d . . . . .
C2 C 1.0951(4) 0.6588(3) 0.28066(19) 0.0257(8) Uani 1 1 d . . . . .
C3 C 1.1353(4) 0.6729(4) 0.2177(2) 0.0413(11) Uani 1 1 d . . . . .
H3 H 1.160387 0.754661 0.204590 0.050 Uiso 1 1 calc R . . . .
C4 C 1.1393(5) 0.5671(4) 0.1731(2) 0.0497(13) Uani 1 1 d . . . . .
H4A H 1.167528 0.577208 0.129887 0.060 Uiso 1 1 calc R . . . .
C5 C 1.1027(4) 0.4486(4) 0.1914(2) 0.0368(10) Uani 1 1 d . . . . .
H5 H 1.103338 0.377393 0.160376 0.044 Uiso 1 1 calc R . . . .
C6 C 1.0651(3) 0.4339(4) 0.2552(2) 0.0283(9) Uani 1 1 d . . . . .
H6 H 1.041851 0.351521 0.268432 0.034 Uiso 1 1 calc R . . . .
C7 C 1.0256(3) 0.5185(3) 0.37130(19) 0.0205(8) Uani 1 1 d . . . . .
C8 C 1.0891(4) 0.7778(3) 0.32527(19) 0.0253(8) Uani 1 1 d . . . . .
C9 C 0.6250(3) 0.4191(3) 0.42797(17) 0.0179(6) Uani 1 1 d D U . . .
C10 C 0.5406(5) 0.4851(6) 0.3717(3) 0.0179(12) Uani 0.583(19) 1 d DG U P A 1
C11 C 0.4097(4) 0.4755(8) 0.3631(4) 0.0194(13) Uani 0.583(19) 1 d DG U P A 1
H11 H 0.352088 0.520600 0.324697 0.023 Uiso 0.583(19) 1 calc R . P A 1
C12 C 0.3632(3) 0.3998(9) 0.4108(5) 0.0171(12) Uani 0.583(19) 1 d DG U P A 1
H12 H 0.273742 0.393222 0.404939 0.021 Uiso 0.583(19) 1 calc R . P A 1
C13 C 0.4475(6) 0.3338(8) 0.4670(4) 0.0158(12) Uani 0.583(19) 1 d DG U P A 1
H13 H 0.415726 0.282095 0.499626 0.019 Uiso 0.583(19) 1 calc R . P A 1
C14 C 0.5784(5) 0.3435(6) 0.4756(3) 0.0158(11) Uani 0.583(19) 1 d DG U P A 1
H14 H 0.636057 0.298345 0.514073 0.019 Uiso 0.583(19) 1 calc R . P A 1
C15 C 0.7677(3) 0.4396(3) 0.45219(19) 0.0243(8) Uani 1 1 d . . . . .
C17 C 1.1094(3) 0.0920(3) 0.4611(2) 0.0233(8) Uani 1 1 d . . . . .
C18 C 1.2363(4) -0.0430(4) 0.5453(2) 0.0302(9) Uani 1 1 d . . . . .
H18 H 1.278544 -0.122652 0.557372 0.036 Uiso 1 1 calc R . . . .
C19 C 1.2453(4) 0.0457(4) 0.6002(2) 0.0311(9) Uani 1 1 d . . . . .
H19 H 1.293541 0.029880 0.649149 0.037 Uiso 1 1 calc R . . . .
C20 C 1.1807(3) 0.1582(3) 0.5803(2) 0.0254(8) Uani 1 1 d . . . . .
H20 H 1.185163 0.221460 0.617019 0.030 Uiso 1 1 calc R . . . .
O9 O 0.7762(11) 0.7247(11) 0.2247(8) 0.037(2) Uani 0.583(19) 1 d . . P A 1
H9A H 0.722678 0.785539 0.219561 0.055 Uiso 0.583(19) 1 d G . P A 1
H9B H 0.846997 0.757799 0.247305 0.055 Uiso 0.583(19) 1 d G . P A 1
C16 C 0.5794(11) 0.5695(9) 0.3146(4) 0.021(2) Uani 0.583(19) 1 d . U P A 1
O8 O 0.6970(10) 0.5424(10) 0.3071(5) 0.0272(19) Uani 0.583(19) 1 d . U P A 1
H8 H 0.718448 0.598362 0.280719 0.041 Uiso 0.583(19) 1 calc GR . P A 1
O7 O 0.5093(12) 0.6486(6) 0.2768(4) 0.040(2) Uani 0.583(19) 1 d . U P A 1
O7A O 0.7359(13) 0.5003(14) 0.3137(7) 0.029(2) Uani 0.417(19) 1 d . U P A 2
C16A C 0.6382(17) 0.5434(12) 0.3203(7) 0.021(3) Uani 0.417(19) 1 d . U P A 2
O8A O 0.5796(16) 0.6497(9) 0.2876(6) 0.035(3) Uani 0.417(19) 1 d . U P A 2
H8A H 0.624367 0.683712 0.262707 0.053 Uiso 0.417(19) 1 calc GR . P A 2
O9A O 0.7328(18) 0.7527(17) 0.2143(12) 0.045(4) Uani 0.417(19) 1 d . . P A 2
H9AA H 0.719169 0.807744 0.180046 0.068 Uiso 0.417(19) 1 d G . P A 2
H9AB H 0.797876 0.780758 0.246137 0.068 Uiso 0.417(19) 1 d G . P A 2
C10A C 0.5591(11) 0.4869(12) 0.3651(6) 0.0186(13) Uani 0.417(19) 1 d D U P A 2
C11A C 0.4277(11) 0.4894(13) 0.3522(7) 0.0211(14) Uani 0.417(19) 1 d D U P A 2
H11A H 0.379998 0.536780 0.311208 0.025 Uiso 0.417(19) 1 calc R . P A 2
C12A C 0.3615(9) 0.4273(13) 0.3952(7) 0.0180(14) Uani 0.417(19) 1 d D U P A 2
H12A H 0.271240 0.434629 0.385025 0.022 Uiso 0.417(19) 1 calc R . P A 2
C13A C 0.4298(10) 0.3536(13) 0.4539(7) 0.0162(13) Uani 0.417(19) 1 d D U P A 2
H13A H 0.385747 0.306184 0.482554 0.019 Uiso 0.417(19) 1 calc R . P A 2
C14A C 0.5619(10) 0.3495(11) 0.4705(6) 0.0157(12) Uani 0.417(19) 1 d D U P A 2
H14A H 0.608968 0.299519 0.510501 0.019 Uiso 0.417(19) 1 calc R . P A 2
O6 O 0.8398(2) 0.3427(2) 0.45860(15) 0.0328(7) Uani 1 1 d . . . . .
O5 O 0.8030(2) 0.5529(2) 0.46807(12) 0.0221(5) Uani 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 0.0033 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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O1 Cu1 Cu1 86.51(7) . 3_766
O1 Cu1 O2 167.34(9) . 3_766
O1 Cu1 N1 98.17(10) . .
O1 Cu1 O5 89.13(10) . 3_766
O2 Cu1 Cu1 81.06(7) 3_766 3_766
O2 Cu1 N1 94.47(10) 3_766 .
O2 Cu1 O5 90.52(10) 3_766 3_766
N1 Cu1 Cu1 164.93(8) . 3_766
O6 Cu1 Cu1 89.63(7) . 3_766
O6 Cu1 O1 87.85(11) . .
O6 Cu1 O2 89.71(11) . 3_766
O6 Cu1 N1 104.80(10) . .
O6 Cu1 O5 167.16(10) . 3_766
O5 Cu1 Cu1 77.72(7) 3_766 3_766
O5 Cu1 N1 87.99(10) 3_766 .
C7 O1 Cu1 119.4(2) . .
C7 O2 Cu1 126.2(2) . 3_766
C8 O4 H4 109.5 . .
C17 N1 Cu1 129.1(2) . .
C20 N1 Cu1 114.5(2) . .
C20 N1 C17 116.4(3) . .
C18 N2 C17 116.7(3) . .
H3A N3 H3B 107.9 . .
C17 N3 H3A 108.5 . .
C17 N3 H3B 111.2 . .
C2 C1 C6 119.0(3) . .
C2 C1 C7 121.0(3) . .
C6 C1 C7 119.9(3) . .
C1 C2 C8 122.6(3) . .
C3 C2 C1 119.9(3) . .
C3 C2 C8 117.5(3) . .
C2 C3 H3 119.9 . .
C2 C3 C4 120.1(4) . .
C4 C3 H3 119.9 . .
C3 C4 H4A 119.8 . .
C5 C4 C3 120.4(4) . .
C5 C4 H4A 119.8 . .
C4 C5 H5 120.2 . .
C4 C5 C6 119.6(4) . .
C6 C5 H5 120.2 . .
C1 C6 H6 119.5 . .
C5 C6 C1 121.0(4) . .
C5 C6 H6 119.5 . .
O1 C7 C1 116.9(3) . .
O2 C7 O1 126.1(3) . .
O2 C7 C1 116.9(3) . .
O3 C8 O4 124.5(3) . .
O3 C8 C2 121.7(3) . .
O4 C8 C2 113.7(3) . .
C10 C9 C14 120.0 . .
C10 C9 C15 125.3(3) . .
C14 C9 C15 113.8(3) . .
C10A C9 C15 115.9(6) . .
C14A C9 C15 121.4(5) . .
C14A C9 C10A 122.3(7) . .
C9 C10 C16 125.1(4) . .
C11 C10 C9 120.0 . .
C11 C10 C16 114.9(4) . .
C10 C11 H11 120.0 . .
C10 C11 C12 120.0 . .
C12 C11 H11 120.0 . .
C11 C12 H12 120.0 . .
C13 C12 C11 120.0 . .
C13 C12 H12 120.0 . .
C12 C13 H13 120.0 . .
C14 C13 C12 120.0 . .
C14 C13 H13 120.0 . .
C9 C14 H14 120.0 . .
C13 C14 C9 120.0 . .
C13 C14 H14 120.0 . .
O6 C15 C9 118.3(3) . .
O5 C15 C9 115.5(3) . .
O5 C15 O6 126.1(3) . .
N1 C17 N2 124.3(3) . .
N3 C17 N1 118.2(3) . .
N3 C17 N2 117.5(3) . .
N2 C18 H18 118.6 . .
N2 C18 C19 122.9(3) . .
C19 C18 H18 118.6 . .
C18 C19 H19 121.8 . .
C20 C19 C18 116.4(3) . .
C20 C19 H19 121.8 . .
N1 C20 C19 123.3(3) . .
N1 C20 H20 118.3 . .
C19 C20 H20 118.3 . .
H9A O9 H9B 104.6 . .
O8 C16 C10 113.3(7) . .
O7 C16 C10 123.8(7) . .
O7 C16 O8 122.8(8) . .
C16 O8 H8 109.5 . .
O7A C16A O8A 126.3(12) . .
O7A C16A C10A 125.2(10) . .
O8A C16A C10A 108.4(12) . .
C16A O8A H8A 109.5 . .
H9AA O9A H9AB 104.5 . .
C9 C10A C16A 116.3(9) . .
C11A C10A C9 115.4(9) . .
C11A C10A C16A 128.2(10) . .
C10A C11A H11A 118.0 . .
C12A C11A C10A 124.0(9) . .
C12A C11A H11A 118.0 . .
C11A C12A H12A 120.7 . .
C11A C12A C13A 118.6(8) . .
C13A C12A H12A 120.7 . .
C12A C13A H13A 120.0 . .
C14A C13A C12A 119.9(8) . .
C14A C13A H13A 120.0 . .
C9 C14A H14A 120.3 . .
C13A C14A C9 119.4(8) . .
C13A C14A H14A 120.3 . .
C15 O6 Cu1 116.2(2) . .
C15 O5 Cu1 130.2(2) . 3_766
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 Cu1 2.6817(8) 3_766
Cu1 O1 1.969(2) .
Cu1 O2 1.970(2) 3_766
Cu1 N1 2.201(3) .
Cu1 O6 1.965(2) .
Cu1 O5 1.971(2) 3_766
O1 C7 1.269(4) .
O2 C7 1.263(4) .
O3 C8 1.218(4) .
O4 H4 0.8400 .
O4 C8 1.313(4) .
N1 C17 1.350(4) .
N1 C20 1.342(4) .
N2 C17 1.358(4) .
N2 C18 1.339(4) .
N3 H3A 0.8661 .
N3 H3B 0.8672 .
N3 C17 1.342(4) .
C1 C2 1.397(5) .
C1 C6 1.398(5) .
C1 C7 1.495(5) .
C2 C3 1.378(5) .
C2 C8 1.514(5) .
C3 H3 0.9500 .
C3 C4 1.400(6) .
C4 H4A 0.9500 .
C4 C5 1.374(6) .
C5 H5 0.9500 .
C5 C6 1.378(5) .
C6 H6 0.9500 .
C9 C10 1.3900 .
C9 C14 1.3900 .
C9 C15 1.510(4) .
C9 C10A 1.406(11) .
C9 C14A 1.391(11) .
C10 C11 1.3900 .
C10 C16 1.536(10) .
C11 H11 0.9500 .
C11 C12 1.3900 .
C12 H12 0.9500 .
C12 C13 1.3900 .
C13 H13 0.9500 .
C13 C14 1.3900 .
C14 H14 0.9500 .
C15 O6 1.267(4) .
C15 O5 1.259(4) .
C18 H18 0.9500 .
C18 C19 1.376(5) .
C19 H19 0.9500 .
C19 C20 1.371(5) .
C20 H20 0.9500 .
O9 H9A 0.8497 .
O9 H9B 0.8486 .
C16 O8 1.350(9) .
C16 O7 1.220(11) .
O8 H8 0.8400 .
O7A C16A 1.188(18) .
C16A O8A 1.348(15) .
C16A C10A 1.478(18) .
O8A H8A 0.8400 .
O9A H9AA 0.8500 .
O9A H9AB 0.8499 .
C10A C11A 1.382(10) .
C11A H11A 0.9500 .
C11A C12A 1.381(10) .
C12A H12A 0.9500 .
C12A C13A 1.393(9) .
C13A H13A 0.9500 .
C13A C14A 1.385(9) .
C14A H14A 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4 N2 0.84 1.84 2.673(4) 170.7 1_565 yes
O9 H9B O3 0.85 2.04 2.882(12) 172.3 . yes
O8 H8 O9 0.84 1.90 2.739(17) 176.8 . yes
O8A H8A O9A 0.84 1.82 2.66(3) 175.3 . yes
O9A H9AA O7A 0.85 2.07 2.68(3) 128.7 2_655 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
Cu1 O1 C7 O2 -10.5(4) . .
Cu1 O1 C7 C1 166.7(2) . .
Cu1 O2 C7 O1 7.8(5) 3_766 .
Cu1 O2 C7 C1 -169.4(2) 3_766 .
Cu1 N1 C17 N2 177.7(2) . .
Cu1 N1 C17 N3 -2.7(5) . .
Cu1 N1 C20 C19 -178.4(3) . .
N2 C18 C19 C20 1.2(6) . .
C1 C2 C3 C4 1.2(6) . .
C1 C2 C8 O3 -102.8(4) . .
C1 C2 C8 O4 81.8(4) . .
C2 C1 C6 C5 -0.1(5) . .
C2 C1 C7 O1 -160.5(3) . .
C2 C1 C7 O2 16.9(5) . .
C2 C3 C4 C5 0.3(7) . .
C3 C2 C8 O3 76.5(5) . .
C3 C2 C8 O4 -98.9(4) . .
C3 C4 C5 C6 -1.7(6) . .
C4 C5 C6 C1 1.6(6) . .
C6 C1 C2 C3 -1.2(5) . .
C6 C1 C2 C8 178.1(3) . .
C6 C1 C7 O1 16.2(5) . .
C6 C1 C7 O2 -166.3(3) . .
C7 C1 C2 C3 175.5(3) . .
C7 C1 C2 C8 -5.2(5) . .
C7 C1 C6 C5 -177.0(3) . .
C8 C2 C3 C4 -178.2(4) . .
C9 C10 C11 C12 0.0 . .
C9 C10 C16 O8 21.2(10) . .
C9 C10 C16 O7 -162.6(8) . .
C9 C15 O6 Cu1 -175.7(2) . .
C9 C15 O5 Cu1 179.3(2) . 3_766
C9 C10A C11A C12A -2.1(13) . .
C10 C9 C14 C13 0.0 . .
C10 C9 C15 O6 -130.1(5) . .
C10 C9 C15 O5 53.7(5) . .
C10 C11 C12 C13 0.0 . .
C11 C10 C16 O8 -157.6(6) . .
C11 C10 C16 O7 18.6(10) . .
C11 C12 C13 C14 0.0 . .
C12 C13 C14 C9 0.0 . .
C14 C9 C10 C11 0.0 . .
C14 C9 C10 C16 -178.7(8) . .
C14 C9 C15 O6 61.2(5) . .
C14 C9 C15 O5 -115.0(4) . .
C15 C9 C10 C11 -168.0(3) . .
C15 C9 C10 C16 13.2(9) . .
C15 C9 C14 C13 169.3(3) . .
C15 C9 C10A C16A 14.7(13) . .
C15 C9 C10A C11A -166.9(6) . .
C15 C9 C14A C13A 167.5(6) . .
C17 N1 C20 C19 -1.0(5) . .
C17 N2 C18 C19 -1.5(6) . .
C18 N2 C17 N1 0.4(5) . .
C18 N2 C17 N3 -179.2(3) . .
C18 C19 C20 N1 0.1(6) . .
C20 N1 C17 N2 0.8(5) . .
C20 N1 C17 N3 -179.6(3) . .
C16 C10 C11 C12 178.8(7) . .
O7A C16A C10A C9 31(2) . .
O7A C16A C10A C11A -147.2(14) . .
C16A C10A C11A C12A 176.0(13) . .
O8A C16A C10A C9 -150.0(10) . .
O8A C16A C10A C11A 31.9(15) . .
C10A C9 C15 O6 -123.9(7) . .
C10A C9 C15 O5 59.9(8) . .
C10A C9 C14A C13A -4.7(12) . .
C10A C11A C12A C13A -2.4(13) . .
C11A C12A C13A C14A 3.5(12) . .
C12A C13A C14A C9 -0.1(12) . .
C14A C9 C15 O6 63.5(8) . .
C14A C9 C15 O5 -112.8(8) . .
C14A C9 C10A C16A -172.7(11) . .
C14A C9 C10A C11A 5.7(12) . .
O6 C15 O5 Cu1 3.4(5) . 3_766
O5 C15 O6 Cu1 0.1(5) . .
