# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_a170813b
_database_code_depnum_ccdc_archive 'CCDC 1821752'
_audit_update_record             
;
2018-02-03 deposited with the CCDC.
2018-08-15 downloaded from the CCDC.
;
_audit_creation_date             2017-10-25
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C50 H35 Cu N7 O6'
_chemical_formula_sum            'C50 H35 Cu N7 O6'
_chemical_formula_weight         893.39
_chemical_melting_point          ?
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'
Cu Cu -1.9646 0.5888 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1100(5)
_cell_length_b                   10.9172(8)
_cell_length_c                   13.7599(10)
_cell_angle_alpha                82.193(6)
_cell_angle_beta                 87.050(6)
_cell_angle_gamma                72.875(6)
_cell_volume                     1011.16(13)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1663
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.2410
_cell_measurement_theta_min      4.2690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.288
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             461
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2331
_diffrn_reflns_av_unetI/netI     0.2909
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7041
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.071
_diffrn_reflns_theta_max         67.071
_diffrn_reflns_theta_min         4.272
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  32.00   1.00    2.32    --  -41.24  57.00   0.00  101
  2  ω   -113.00 -13.00   1.00    2.32    --  -41.24 -57.00-150.00  100
  3  ω    -96.00  -2.00   1.00    2.32    --  -41.24 125.00  30.00   94
  4  ω   -116.00 -17.00   1.00    2.32    --  -41.24 -38.00  90.00   99
  5  ω     34.00 121.00   1.00    9.28    --  107.08-125.00-180.00   87
  6  ω     34.00 121.00   1.00    9.28    --  107.08-125.00   0.00   87
  7  ω     81.00 178.00   1.00    9.28    --  107.08  45.00 -60.00   97
  8  ω     25.00 109.00   1.00    9.28    --  107.08 -95.00-150.00   84
  9  ω     78.00 178.00   1.00    9.28    --  107.08  61.00-180.00  100
 10  ω     94.00 178.00   1.00    9.28    --  107.08 125.00 120.00   84
 11  ω     37.00  80.00   1.00    9.28    --  107.08 -30.00 -30.00   43
 12  ω    108.00 135.00   1.00    9.28    --  107.08 -30.00 -30.00   27
 13  ω     37.00  88.00   1.00    9.28    --  107.08 -45.00-180.00   51
 14  ω     85.00 145.00   1.00    9.28    --  107.08  77.00  60.00   60
 15  ω     94.00 127.00   1.00    9.28    --  107.08 125.00   0.00   33
 16  ω     49.00 140.00   1.00    9.28    --  107.08 -77.00 -30.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1153001000
_diffrn_orient_matrix_UB_12      -0.0202661000
_diffrn_orient_matrix_UB_13      0.0957520000
_diffrn_orient_matrix_UB_21      0.0635103000
_diffrn_orient_matrix_UB_22      0.1062081000
_diffrn_orient_matrix_UB_23      0.0407283000
_diffrn_orient_matrix_UB_31      -0.1846239000
_diffrn_orient_matrix_UB_32      0.1023088000
_diffrn_orient_matrix_UB_33      -0.0441062000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1711
_reflns_number_total             3601
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_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)'
_refine_diff_density_max         1.842
_refine_diff_density_min         -2.015
_refine_diff_density_rms         0.190
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3601
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.2252
_refine_ls_R_factor_gt           0.1637
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3632
_refine_ls_wR_factor_ref         0.4191
_refine_special_details          ?
_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
2. Uiso/Uaniso restraints and constraints
Uanis(C2) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.002
Uanis(C22) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.002
Uanis(C22) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C25)
\\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.005
Uanis(C9) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
3. Others
 Fixed Sof: H24(0.5) N4(0.5) H4A(0.5) H4B(0.5)
4.a Rotating group:
 N4(H4A,H4B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C24(H24), C25(H25)
4.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.5000 1.0000 0.0000 0.0253(7) Uani 1 2 d S T P . .
O1 O 0.6760(10) 0.8326(6) -0.0245(5) 0.0317(19) Uani 1 1 d . . . . .
O2 O 0.8889(12) 0.8126(6) 0.0922(6) 0.0368(19) Uani 1 1 d . . . . .
O3 O 0.2068(10) 0.9382(6) 0.9331(4) 0.0266(16) Uani 1 1 d . . . . .
H3 H 0.1435 1.0148 0.9258 0.040 Uiso 1 1 calc GR . . . .
N1 N 0.2866(10) 0.6138(7) 0.4055(6) 0.0200(18) Uani 1 1 d . . . . .
N2 N 0.4224(11) 0.9185(7) 0.1301(6) 0.0245(19) Uani 1 1 d . . . . .
N3 N 0.2559(11) 0.1546(7) 0.4652(7) 0.026(2) Uani 1 1 d . . . . .
C1 C 0.2344(11) 0.7198(8) 0.5813(6) 0.0161(18) Uani 1 1 d . U . . .
C2 C 0.2646(11) 0.7916(8) 0.4919(6) 0.0179(18) Uani 1 1 d . U . . .
H2 H 0.2663 0.8768 0.4898 0.022 Uiso 1 1 calc R . . . .
C3 C 0.2912(11) 0.7338(8) 0.4088(6) 0.0150(18) Uani 1 1 d . . . . .
C4 C 0.2532(10) 0.5452(9) 0.4915(7) 0.018(2) Uani 1 1 d . . . . .
C5 C 0.2284(11) 0.5950(8) 0.5792(6) 0.020(2) Uani 1 1 d . . . . .
H5 H 0.2077 0.5450 0.6368 0.024 Uiso 1 1 calc R . . . .
C6 C 0.3380(11) 0.8016(8) 0.3116(6) 0.0181(18) Uani 1 1 d . U . . .
C7 C 0.3683(12) 0.9214(9) 0.3015(7) 0.0212(19) Uani 1 1 d . U . . .
H7 H 0.3608 0.9650 0.3559 0.025 Uiso 1 1 calc R . . . .
C8 C 0.4106(11) 0.9768(8) 0.2086(6) 0.0172(18) Uani 1 1 d . U . . .
H8 H 0.4310 1.0579 0.2021 0.021 Uiso 1 1 calc R . . . .
C9 C 0.3901(15) 0.8042(9) 0.1384(7) 0.027(2) Uani 1 1 d . U . . .
H9 H 0.3958 0.7639 0.0825 0.032 Uiso 1 1 calc R . . . .
C10 C 0.3477(15) 0.7426(9) 0.2289(7) 0.026(2) Uani 1 1 d . . . . .
H10 H 0.3262 0.6620 0.2331 0.031 Uiso 1 1 calc R . . . .
C11 C 0.2503(12) 0.4102(9) 0.4816(7) 0.020(2) Uani 1 1 d . . . . .
C12 C 0.2233(12) 0.3246(9) 0.5646(7) 0.022(2) Uani 1 1 d . . . . .
H12 H 0.2027 0.3504 0.6269 0.026 Uiso 1 1 calc R . . . .
C13 C 0.2288(13) 0.2021(9) 0.5491(7) 0.025(2) Uani 1 1 d . . . . .
H13 H 0.2113 0.1466 0.6041 0.030 Uiso 1 1 calc R . . . .
C14 C 0.2759(16) 0.2404(10) 0.3885(8) 0.034(3) Uani 1 1 d . . . . .
H14 H 0.2911 0.2130 0.3267 0.041 Uiso 1 1 calc R . . . .
C15 C 0.2758(13) 0.3638(9) 0.3936(7) 0.024(2) Uani 1 1 d . . . . .
H15 H 0.2931 0.4165 0.3369 0.028 Uiso 1 1 calc R . . . .
C16 C 0.2139(12) 0.7768(9) 0.6753(7) 0.020(2) Uani 1 1 d . . . . .
C17 C 0.1301(12) 0.9083(9) 0.6785(6) 0.023(2) Uani 1 1 d . . . . .
H17 H 0.0762 0.9607 0.6217 0.027 Uiso 1 1 calc R . . . .
C18 C 0.1244(12) 0.9627(9) 0.7620(7) 0.022(2) Uani 1 1 d . . . . .
H18 H 0.0683 1.0513 0.7614 0.027 Uiso 1 1 calc R . . . .
C19 C 0.2023(12) 0.8865(9) 0.8493(7) 0.023(2) Uani 1 1 d . . . . .
C20 C 0.2848(16) 0.7534(10) 0.8481(7) 0.033(2) Uani 1 1 d . . . . .
H20 H 0.3384 0.7014 0.9051 0.039 Uiso 1 1 calc R . . . .
C21 C 0.2872(15) 0.6996(9) 0.7646(8) 0.032(3) Uani 1 1 d . . . . .
H21 H 0.3378 0.6106 0.7658 0.038 Uiso 1 1 calc R . . . .
C22 C 0.8239(13) 0.7689(8) 0.0291(7) 0.022(2) Uani 1 1 d . U . . .
C23 C 0.9122(16) 0.6283(10) 0.0138(8) 0.032(2) Uani 1 1 d . . . . .
C24 C 1.023(2) 0.5436(12) 0.0877(11) 0.050(3) Uani 1 1 d . U . . .
H24 H 1.0358 0.5715 0.1472 0.060 Uiso 0.5 1 calc R . . A 2
C25 C 0.8841(17) 0.5863(11) -0.0720(9) 0.041(3) Uani 1 1 d . U . . .
H25 H 0.8039 0.6429 -0.1200 0.049 Uiso 1 1 calc R . . . .
N4 N 1.009(3) 0.570(2) 0.1889(17) 0.058(7) Uani 0.5 1 d . . . B 1
H4A H 0.9585 0.6510 0.1917 0.070 Uiso 0.5 1 d GR . . B 1
H4B H 0.9345 0.5279 0.2201 0.070 Uiso 0.5 1 d GR . . B 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.948(6) 2_675 ?
Cu1 O1 1.948(6) . ?
Cu1 N2 2.014(7) . ?
Cu1 N2 2.014(7) 2_675 ?
O1 C22 1.282(12) . ?
O2 C22 1.216(13) . ?
O3 H3 0.8200 . ?
O3 C19 1.357(13) . ?
N1 C3 1.327(12) . ?
N1 C4 1.361(11) . ?
N2 C8 1.314(13) . ?
N2 C9 1.323(13) . ?
N3 C13 1.311(14) . ?
N3 C14 1.344(12) . ?
C1 C2 1.409(10) . ?
C1 C5 1.380(13) . ?
C1 C16 1.492(14) . ?
C2 H2 0.9300 . ?
C2 C3 1.358(13) . ?
C3 C6 1.509(10) . ?
C4 C5 1.373(14) . ?
C4 C11 1.504(14) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(13) . ?
C6 C10 1.371(14) . ?
C7 H7 0.9300 . ?
C7 C8 1.396(11) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.395(12) . ?
C10 H10 0.9300 . ?
C11 C12 1.418(11) . ?
C11 C15 1.358(14) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(15) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.358(15) . ?
C15 H15 0.9300 . ?
C16 C17 1.389(14) . ?
C16 C21 1.420(13) . ?
C17 H17 0.9300 . ?
C17 C18 1.357(14) . ?
C18 H18 0.9300 . ?
C18 C19 1.402(12) . ?
C19 C20 1.400(15) . ?
C20 H20 0.9300 . ?
C20 C21 1.357(16) . ?
C21 H21 0.9300 . ?
C22 C23 1.517(13) . ?
C23 C24 1.379(17) . ?
C23 C25 1.367(18) . ?
C24 H24 0.9300 . ?
C24 C25 1.418(17) 2_765 ?
C24 N4 1.45(3) . ?
C25 C24 1.418(17) 2_765 ?
C25 H25 0.9300 . ?
N4 H4A 0.8613 . ?
N4 H4B 0.8613 . ?

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
_geom_angle_publ_flag
O1 Cu1 O1 180.0(2) 2_675 . ?
O1 Cu1 N2 89.7(3) . . ?
O1 Cu1 N2 90.3(3) 2_675 . ?
O1 Cu1 N2 89.7(3) 2_675 2_675 ?
O1 Cu1 N2 90.3(3) . 2_675 ?
N2 Cu1 N2 180.0 2_675 . ?
C22 O1 Cu1 123.9(8) . . ?
C19 O3 H3 109.5 . . ?
C3 N1 C4 117.3(9) . . ?
C8 N2 Cu1 119.9(6) . . ?
C8 N2 C9 119.3(8) . . ?
C9 N2 Cu1 120.8(7) . . ?
C13 N3 C14 113.4(9) . . ?
C2 C1 C16 120.6(8) . . ?
C5 C1 C2 118.0(9) . . ?
C5 C1 C16 121.4(7) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.6(9) . . ?
C3 C2 H2 120.7 . . ?
N1 C3 C2 124.2(7) . . ?
N1 C3 C6 114.2(8) . . ?
C2 C3 C6 121.5(8) . . ?
N1 C4 C5 122.5(9) . . ?
N1 C4 C11 114.0(9) . . ?
C5 C4 C11 123.5(7) . . ?
C1 C5 H5 120.3 . . ?
C4 C5 C1 119.5(7) . . ?
C4 C5 H5 120.3 . . ?
C7 C6 C3 123.0(9) . . ?
C10 C6 C3 118.9(8) . . ?
C10 C6 C7 118.1(8) . . ?
C6 C7 H7 120.5 . . ?
C6 C7 C8 119.1(9) . . ?
C8 C7 H7 120.5 . . ?
N2 C8 C7 122.3(9) . . ?
N2 C8 H8 118.8 . . ?
C7 C8 H8 118.8 . . ?
N2 C9 H9 119.2 . . ?
N2 C9 C10 121.7(10) . . ?
C10 C9 H9 119.2 . . ?
C6 C10 C9 119.6(9) . . ?
C6 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C4 121.2(9) . . ?
C15 C11 C4 122.1(8) . . ?
C15 C11 C12 116.7(9) . . ?
C11 C12 H12 121.4 . . ?
C13 C12 C11 117.2(10) . . ?
C13 C12 H12 121.4 . . ?
N3 C13 C12 127.1(8) . . ?
N3 C13 H13 116.4 . . ?
C12 C13 H13 116.4 . . ?
N3 C14 H14 117.3 . . ?
N3 C14 C15 125.5(11) . . ?
C15 C14 H14 117.3 . . ?
C11 C15 C14 120.0(8) . . ?
C11 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C1 121.5(7) . . ?
C17 C16 C21 117.2(10) . . ?
C21 C16 C1 121.3(9) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 C16 121.9(8) . . ?
C18 C17 H17 119.0 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.6(9) . . ?
C19 C18 H18 119.7 . . ?
O3 C19 C18 122.2(9) . . ?
O3 C19 C20 119.3(8) . . ?
C20 C19 C18 118.4(10) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.6(9) . . ?
C21 C20 H20 119.7 . . ?
C16 C21 H21 119.4 . . ?
C20 C21 C16 121.2(10) . . ?
C20 C21 H21 119.4 . . ?
O1 C22 C23 115.9(10) . . ?
O2 C22 O1 124.3(9) . . ?
O2 C22 C23 119.8(8) . . ?
C24 C23 C22 118.9(12) . . ?
C25 C23 C22 120.6(9) . . ?
C25 C23 C24 120.5(11) . . ?
C23 C24 H24 120.3 . . ?
C23 C24 C25 119.4(14) . 2_765 ?
C23 C24 N4 122.9(13) . . ?
C25 C24 H24 120.3 2_765 . ?
C25 C24 N4 115.8(13) 2_765 . ?
C23 C25 C24 120.0(11) . 2_765 ?
C23 C25 H25 120.0 . . ?
C24 C25 H25 120.0 2_765 . ?
C24 N4 H4A 110.0 . . ?
C24 N4 H4B 107.6 . . ?
H4A N4 H4B 109.3 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C22 O2 -11.3(13) . . . . ?
Cu1 O1 C22 C23 165.5(6) . . . . ?
Cu1 N2 C8 C7 -176.3(6) . . . . ?
Cu1 N2 C9 C10 176.1(7) . . . . ?
O1 C22 C23 C24 -158.4(11) . . . . ?
O1 C22 C23 C25 22.1(14) . . . . ?
O2 C22 C23 C24 18.6(15) . . . . ?
O2 C22 C23 C25 -160.9(11) . . . . ?
O3 C19 C20 C21 -178.2(9) . . . . ?
N1 C3 C6 C7 -173.5(7) . . . . ?
N1 C3 C6 C10 7.6(11) . . . . ?
N1 C4 C5 C1 1.0(12) . . . . ?
N1 C4 C11 C12 178.1(7) . . . . ?
N1 C4 C11 C15 -1.1(11) . . . . ?
N2 C9 C10 C6 0.3(15) . . . . ?
N3 C14 C15 C11 -1.3(16) . . . . ?
C1 C2 C3 N1 1.5(12) . . . . ?
C1 C2 C3 C6 -175.8(7) . . . . ?
C1 C16 C17 C18 -174.8(8) . . . . ?
C1 C16 C21 C20 173.9(9) . . . . ?
C2 C1 C5 C4 0.5(11) . . . . ?
C2 C1 C16 C17 31.7(12) . . . . ?
C2 C1 C16 C21 -145.4(9) . . . . ?
C2 C3 C6 C7 4.0(12) . . . . ?
C2 C3 C6 C10 -174.9(8) . . . . ?
C3 N1 C4 C5 -1.2(11) . . . . ?
C3 N1 C4 C11 -180.0(7) . . . . ?
C3 C6 C7 C8 -179.9(7) . . . . ?
C3 C6 C10 C9 179.8(8) . . . . ?
C4 N1 C3 C2 0.0(12) . . . . ?
C4 N1 C3 C6 177.4(7) . . . . ?
C4 C11 C12 C13 -178.1(8) . . . . ?
C4 C11 C15 C14 178.7(9) . . . . ?
C5 C1 C2 C3 -1.7(11) . . . . ?
C5 C1 C16 C17 -149.5(8) . . . . ?
C5 C1 C16 C21 33.3(12) . . . . ?
C5 C4 C11 C12 -0.7(12) . . . . ?
C5 C4 C11 C15 -179.8(8) . . . . ?
C6 C7 C8 N2 0.0(13) . . . . ?
C7 C6 C10 C9 0.8(13) . . . . ?
C8 N2 C9 C10 -1.4(14) . . . . ?
C9 N2 C8 C7 1.2(13) . . . . ?
C10 C6 C7 C8 -1.0(12) . . . . ?
C11 C4 C5 C1 179.6(7) . . . . ?
C11 C12 C13 N3 -0.2(14) . . . . ?
C12 C11 C15 C14 -0.5(13) . . . . ?
C13 N3 C14 C15 2.1(15) . . . . ?
C14 N3 C13 C12 -1.4(14) . . . . ?
C15 C11 C12 C13 1.2(12) . . . . ?
C16 C1 C2 C3 177.1(7) . . . . ?
C16 C1 C5 C4 -178.3(7) . . . . ?
C16 C17 C18 C19 -0.7(13) . . . . ?
C17 C16 C21 C20 -3.4(14) . . . . ?
C17 C18 C19 O3 177.1(8) . . . . ?
C17 C18 C19 C20 -0.3(13) . . . . ?
C18 C19 C20 C21 -0.7(15) . . . . ?
C19 C20 C21 C16 2.6(16) . . . . ?
C21 C16 C17 C18 2.5(12) . . . . ?
C22 C23 C24 C25 -176.2(11) . . . 2_765 ?
C22 C23 C24 N4 20(2) . . . . ?
C22 C23 C25 C24 176.2(11) . . . 2_765 ?
C24 C23 C25 C24 -3(2) . . . 2_765 ?
C25 C23 C24 C25 3(2) . . . 2_765 ?
C25 C23 C24 N4 -160.5(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.390
_oxdiff_exptl_absorpt_empirical_full_min 0.255
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a161107e
_database_code_depnum_ccdc_archive 'CCDC 1821753'
_audit_update_record             
;
2018-02-03 deposited with the CCDC.
2018-08-15 downloaded from the CCDC.
;
_audit_creation_date             2016-11-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C50 H34 Cu N6 O6'
_chemical_formula_sum            'C50 H34 Cu N6 O6'
_chemical_formula_weight         878.37
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0631(4)
_cell_length_b                   10.9098(7)
_cell_length_c                   13.8073(8)
_cell_angle_alpha                82.556(5)
_cell_angle_beta                 89.225(5)
_cell_angle_gamma                73.069(6)
_cell_volume                     1008.93(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2377
_cell_measurement_temperature    118.6(3)
_cell_measurement_theta_max      28.2280
_cell_measurement_theta_min      4.0510
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.603
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             453
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0839
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6646
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         3.329
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      118.6(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  33.00   1.00   12.41    --   11.08 -57.00  90.00   93
  2  ω    -19.00  71.00   1.00   12.41    --   11.08  77.00   0.00   90
  3  ω    -17.00  79.00   1.00   12.41    --   11.08  57.00-120.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0959201000
_diffrn_orient_matrix_UB_12      0.0366940000
_diffrn_orient_matrix_UB_13      0.0120372000
_diffrn_orient_matrix_UB_21      0.0237104000
_diffrn_orient_matrix_UB_22      0.0578931000
_diffrn_orient_matrix_UB_23      -0.0167361000
_diffrn_orient_matrix_UB_31      -0.0355492000
_diffrn_orient_matrix_UB_32      -0.0012757000
_diffrn_orient_matrix_UB_33      -0.0475480000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2894
_reflns_number_total             3554
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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)'
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.699
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         3554
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0365P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1064
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C24(H24), C25(H25)
2.b Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.5000 1.0000 0.0000 0.01425(17) Uani 1 2 d S T P . .
O1 O 0.6715(3) 0.83108(19) -0.02372(13) 0.0178(5) Uani 1 1 d . . . . .
O2 O 0.9038(3) 0.8120(2) 0.09079(15) 0.0272(5) Uani 1 1 d . . . . .
O3 O 0.2048(3) 0.9383(2) 0.93108(13) 0.0214(5) Uani 1 1 d . . . . .
H3 H 0.1528 1.0167 0.9220 0.032 Uiso 1 1 calc GR . . . .
N1 N 0.2845(3) 0.6194(2) 0.40128(15) 0.0129(5) Uani 1 1 d . . . . .
N2 N 0.4249(3) 0.9224(2) 0.12802(15) 0.0136(5) Uani 1 1 d . . . . .
N3 N 0.2470(3) 0.1623(2) 0.45785(17) 0.0191(6) Uani 1 1 d . . . . .
C1 C 0.2411(4) 0.7259(3) 0.57750(19) 0.0120(6) Uani 1 1 d . . . . .
C2 C 0.2701(4) 0.7971(3) 0.48935(18) 0.0123(6) Uani 1 1 d . . . . .
H2 H 0.2737 0.8818 0.4881 0.015 Uiso 1 1 calc R . . . .
C3 C 0.2933(4) 0.7398(3) 0.40388(19) 0.0123(6) Uani 1 1 d . . . . .
C4 C 0.2546(3) 0.5502(3) 0.48550(18) 0.0113(6) Uani 1 1 d . . . . .
C5 C 0.2343(4) 0.6011(3) 0.57342(19) 0.0130(6) Uani 1 1 d . . . . .
H5 H 0.2159 0.5507 0.6304 0.016 Uiso 1 1 calc R . . . .
C6 C 0.3371(4) 0.8062(3) 0.30922(19) 0.0122(6) Uani 1 1 d . . . . .
C7 C 0.3659(4) 0.9279(3) 0.29902(19) 0.0146(7) Uani 1 1 d . . . . .
H7 H 0.3573 0.9723 0.3528 0.018 Uiso 1 1 calc R . . . .
C8 C 0.4075(4) 0.9824(3) 0.20803(19) 0.0138(6) Uani 1 1 d . . . . .
H8 H 0.4242 1.0645 0.2021 0.017 Uiso 1 1 calc R . . . .
C9 C 0.3939(4) 0.8059(3) 0.13800(19) 0.0182(7) Uani 1 1 d . . . . .
H9 H 0.4019 0.7639 0.0829 0.022 Uiso 1 1 calc R . . . .
C10 C 0.3512(4) 0.7458(3) 0.22515(19) 0.0177(7) Uani 1 1 d . . . . .
H10 H 0.3316 0.6647 0.2284 0.021 Uiso 1 1 calc R . . . .
C11 C 0.2469(4) 0.4178(3) 0.47686(19) 0.0126(6) Uani 1 1 d . . . . .
C12 C 0.2298(4) 0.3305(3) 0.5573(2) 0.0157(7) Uani 1 1 d . . . . .
H12 H 0.2171 0.3554 0.6196 0.019 Uiso 1 1 calc R . . . .
C13 C 0.2317(4) 0.2067(3) 0.5442(2) 0.0192(7) Uani 1 1 d . . . . .
H13 H 0.2216 0.1503 0.5993 0.023 Uiso 1 1 calc R . . . .
C14 C 0.2579(4) 0.2480(3) 0.3807(2) 0.0205(7) Uani 1 1 d . . . . .
H14 H 0.2652 0.2212 0.3191 0.025 Uiso 1 1 calc R . . . .
C15 C 0.2588(4) 0.3729(3) 0.3863(2) 0.0166(7) Uani 1 1 d . . . . .
H15 H 0.2674 0.4272 0.3297 0.020 Uiso 1 1 calc R . . . .
C16 C 0.2231(4) 0.7815(3) 0.67053(19) 0.0128(6) Uani 1 1 d . . . . .
C17 C 0.1410(4) 0.9131(3) 0.67322(19) 0.0148(7) Uani 1 1 d . . . . .
H17 H 0.0919 0.9665 0.6155 0.018 Uiso 1 1 calc R . . . .
C18 C 0.1301(4) 0.9671(3) 0.75840(19) 0.0151(6) Uani 1 1 d . . . . .
H18 H 0.0733 1.0555 0.7579 0.018 Uiso 1 1 calc R . . . .
C19 C 0.2043(4) 0.8889(3) 0.84572(19) 0.0141(6) Uani 1 1 d . . . . .
C20 C 0.2821(4) 0.7568(3) 0.84550(19) 0.0190(7) Uani 1 1 d . . . . .
H20 H 0.3282 0.7034 0.9036 0.023 Uiso 1 1 calc R . . . .
C21 C 0.2913(4) 0.7045(3) 0.75922(19) 0.0174(7) Uani 1 1 d . . . . .
H21 H 0.3442 0.6157 0.7601 0.021 Uiso 1 1 calc R . . . .
C22 C 0.8256(4) 0.7677(3) 0.0281(2) 0.0194(7) Uani 1 1 d . . . . .
C23 C 0.9147(4) 0.6295(3) 0.0126(2) 0.0170(7) Uani 1 1 d . . . . .
C24 C 0.8488(5) 0.5775(3) -0.0622(2) 0.0270(8) Uani 1 1 d . . . . .
H24 H 0.7467 0.6292 -0.1042 0.032 Uiso 1 1 calc R . . . .
C25 C 0.9330(5) 0.4503(3) -0.0746(2) 0.0292(8) Uani 1 1 d . . . . .
H25 H 0.8876 0.4171 -0.1254 0.035 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.954(2) . ?
Cu1 O1 1.954(2) 2_675 ?
Cu1 N2 1.993(2) . ?
Cu1 N2 1.993(2) 2_675 ?
O1 C22 1.276(3) . ?
O2 C22 1.251(3) . ?
O3 H3 0.8200 . ?
O3 C19 1.359(3) . ?
N1 C3 1.339(4) . ?
N1 C4 1.351(3) . ?
N2 C8 1.342(3) . ?
N2 C9 1.342(4) . ?
N3 C13 1.335(4) . ?
N3 C14 1.340(4) . ?
C1 C2 1.403(4) . ?
C1 C5 1.384(4) . ?
C1 C16 1.479(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.391(4) . ?
C3 C6 1.484(4) . ?
C4 C5 1.388(4) . ?
C4 C11 1.481(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.390(4) . ?
C6 C10 1.396(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.384(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.368(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.396(4) . ?
C11 C15 1.394(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.377(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.388(4) . ?
C16 C21 1.397(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.373(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.395(4) . ?
C19 C20 1.384(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.379(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.497(4) . ?
C23 C24 1.387(4) . ?
C23 C25 1.391(4) 2_765 ?
C24 H24 0.9300 . ?
C24 C25 1.374(5) . ?
C25 C23 1.391(4) 2_765 ?
C25 H25 0.9300 . ?

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
_geom_angle_publ_flag
O1 Cu1 O1 180.0 . 2_675 ?
O1 Cu1 N2 90.46(8) . . ?
O1 Cu1 N2 89.54(8) 2_675 . ?
O1 Cu1 N2 89.54(8) . 2_675 ?
O1 Cu1 N2 90.46(8) 2_675 2_675 ?
N2 Cu1 N2 180.00(11) . 2_675 ?
C22 O1 Cu1 124.04(19) . . ?
C19 O3 H3 109.5 . . ?
C3 N1 C4 118.5(2) . . ?
C8 N2 Cu1 121.9(2) . . ?
C9 N2 Cu1 120.92(19) . . ?
C9 N2 C8 117.2(2) . . ?
C13 N3 C14 115.3(3) . . ?
C2 C1 C16 121.1(3) . . ?
C5 C1 C2 117.0(3) . . ?
C5 C1 C16 121.9(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
N1 C3 C2 122.7(2) . . ?
N1 C3 C6 114.9(3) . . ?
C2 C3 C6 122.4(3) . . ?
N1 C4 C5 121.5(3) . . ?
N1 C4 C11 115.3(2) . . ?
C5 C4 C11 123.2(2) . . ?
C1 C5 C4 120.9(3) . . ?
C1 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C7 C6 C3 123.2(3) . . ?
C7 C6 C10 117.1(3) . . ?
C10 C6 C3 119.7(3) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.4(3) . . ?
C8 C7 H7 120.3 . . ?
N2 C8 C7 123.1(3) . . ?
N2 C8 H8 118.4 . . ?
C7 C8 H8 118.4 . . ?
N2 C9 H9 118.4 . . ?
N2 C9 C10 123.2(3) . . ?
C10 C9 H9 118.4 . . ?
C6 C10 H10 120.0 . . ?
C9 C10 C6 119.9(3) . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C4 122.9(3) . . ?
C15 C11 C4 121.1(2) . . ?
C15 C11 C12 115.9(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12 120.1 . . ?
N3 C13 C12 124.6(3) . . ?
N3 C13 H13 117.7 . . ?
C12 C13 H13 117.7 . . ?
N3 C14 H14 117.7 . . ?
N3 C14 C15 124.5(3) . . ?
C15 C14 H14 117.7 . . ?
C11 C15 H15 120.0 . . ?
C14 C15 C11 119.9(3) . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C1 121.4(2) . . ?
C17 C16 C21 117.1(3) . . ?
C21 C16 C1 121.6(3) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 C16 122.1(2) . . ?
C18 C17 H17 118.9 . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
O3 C19 C18 122.1(3) . . ?
O3 C19 C20 118.7(2) . . ?
C20 C19 C18 119.2(3) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.1(3) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 H21 119.2 . . ?
C20 C21 C16 121.7(3) . . ?
C20 C21 H21 119.2 . . ?
O1 C22 C23 116.5(3) . . ?
O2 C22 O1 124.9(3) . . ?
O2 C22 C23 118.6(2) . . ?
C24 C23 C22 121.8(3) . . ?
C24 C23 C25 118.4(3) . 2_765 ?
C25 C23 C22 119.9(3) 2_765 . ?
C23 C24 H24 119.7 . . ?
C25 C24 C23 120.6(3) . . ?
C25 C24 H24 119.7 . . ?
C23 C25 H25 119.5 2_765 . ?
C24 C25 C23 121.1(3) . 2_765 ?
C24 C25 H25 119.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C22 O2 -11.2(4) . . . . ?
Cu1 O1 C22 C23 167.71(18) . . . . ?
Cu1 N2 C8 C7 -176.45(18) . . . . ?
Cu1 N2 C9 C10 176.9(2) . . . . ?
O1 C22 C23 C24 7.7(4) . . . . ?
O1 C22 C23 C25 -171.8(3) . . . 2_765 ?
O2 C22 C23 C24 -173.3(3) . . . . ?
O2 C22 C23 C25 7.1(4) . . . 2_765 ?
O3 C19 C20 C21 -177.3(2) . . . . ?
N1 C3 C6 C7 -175.3(2) . . . . ?
N1 C3 C6 C10 4.6(3) . . . . ?
N1 C4 C5 C1 1.0(4) . . . . ?
N1 C4 C11 C12 175.8(2) . . . . ?
N1 C4 C11 C15 -3.5(3) . . . . ?
N2 C9 C10 C6 0.3(4) . . . . ?
N3 C14 C15 C11 -0.4(4) . . . . ?
C1 C2 C3 N1 1.7(4) . . . . ?
C1 C2 C3 C6 -176.1(2) . . . . ?
C1 C16 C17 C18 -177.5(2) . . . . ?
C1 C16 C21 C20 177.3(2) . . . . ?
C2 C1 C5 C4 -0.3(4) . . . . ?
C2 C1 C16 C17 31.3(4) . . . . ?
C2 C1 C16 C21 -147.4(3) . . . . ?
C2 C3 C6 C7 2.6(4) . . . . ?
C2 C3 C6 C10 -177.5(2) . . . . ?
C3 N1 C4 C5 -0.4(3) . . . . ?
C3 N1 C4 C11 -179.9(2) . . . . ?
C3 C6 C7 C8 179.6(2) . . . . ?
C3 C6 C10 C9 -179.2(2) . . . . ?
C4 N1 C3 C2 -1.0(4) . . . . ?
C4 N1 C3 C6 176.9(2) . . . . ?
C4 C11 C12 C13 -177.3(2) . . . . ?
C4 C11 C15 C14 177.9(2) . . . . ?
C5 C1 C2 C3 -1.0(3) . . . . ?
C5 C1 C16 C17 -150.1(3) . . . . ?
C5 C1 C16 C21 31.2(4) . . . . ?
C5 C4 C11 C12 -3.7(4) . . . . ?
C5 C4 C11 C15 177.0(2) . . . . ?
C6 C7 C8 N2 -1.1(4) . . . . ?
C7 C6 C10 C9 0.7(4) . . . . ?
C8 N2 C9 C10 -1.7(4) . . . . ?
C9 N2 C8 C7 2.1(4) . . . . ?
C10 C6 C7 C8 -0.3(4) . . . . ?
C11 C4 C5 C1 -179.5(2) . . . . ?
C11 C12 C13 N3 -0.8(4) . . . . ?
C12 C11 C15 C14 -1.5(4) . . . . ?
C13 N3 C14 C15 1.6(4) . . . . ?
C14 N3 C13 C12 -1.0(4) . . . . ?
C15 C11 C12 C13 2.0(4) . . . . ?
C16 C1 C2 C3 177.7(2) . . . . ?
C16 C1 C5 C4 -179.0(2) . . . . ?
C16 C17 C18 C19 0.5(4) . . . . ?
C17 C16 C21 C20 -1.5(4) . . . . ?
C17 C18 C19 O3 177.1(2) . . . . ?
C17 C18 C19 C20 -2.2(4) . . . . ?
C18 C19 C20 C21 2.0(4) . . . . ?
C19 C20 C21 C16 -0.2(4) . . . . ?
C21 C16 C17 C18 1.3(4) . . . . ?
C22 C23 C24 C25 -179.9(3) . . . . ?
C23 C24 C25 C23 0.4(5) . . . 2_765 ?
C25 C23 C24 C25 -0.3(5) 2_765 . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-11-07
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.264
_oxdiff_exptl_absorpt_empirical_full_min 0.795
