# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_a180427c
_database_code_depnum_ccdc_archive 'CCDC 1957635'
loop_
_audit_author_name
_audit_author_address
'En-Cui Yang'
;Tianjin Normal University
China
;
_audit_update_record             
;
2019-10-05 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;
_audit_creation_date             2019-06-17
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C50 H34 Cu N6 O7'
_chemical_formula_sum            'C50 H34 Cu N6 O7'
_chemical_formula_weight         894.37
_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 0.0181 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                   7.1213(3)
_cell_length_b                   10.9493(5)
_cell_length_c                   13.8046(6)
_cell_angle_alpha                81.707(4)
_cell_angle_beta                 88.055(4)
_cell_angle_gamma                72.596(4)
_cell_volume                     1016.33(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3515
_cell_measurement_temperature    139.1(3)
_cell_measurement_theta_max      73.8150
_cell_measurement_theta_min      3.2050
_shelx_estimated_absorpt_T_max   0.782
_shelx_estimated_absorpt_T_min   0.738
_exptl_absorpt_coefficient_mu    1.294
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.461
_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  0.0345
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6457
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.063
_diffrn_reflns_theta_max         67.063
_diffrn_reflns_theta_min         3.235
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      139.1(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00  -9.00   1.00    1.57    --  -41.24 -19.00 120.00  107
  2  ω   -116.00 -40.00   1.00    1.57    --  -41.24 -38.00  60.00   76
  3  ω    -81.00 -11.00   1.00    1.57    --  -41.24 125.00-150.00   70
  4  ω     24.00  55.00   1.00    1.57    --   41.24-125.00  30.00   31
  5  ω     29.00  91.00   1.00    1.57    --   41.24-125.00 120.00   62
  6  ω     84.00 164.00   1.00    6.26    --  107.08  45.00  30.00   80
  7  ω     81.00 121.00   1.00    6.26    --  107.08  45.00-150.00   40
  8  ω     79.00 139.00   1.00    6.26    --  107.08 -77.00 -60.00   60
  9  ω     37.00 121.00   1.00    6.26    --  107.08-125.00 -30.00   84
 10  ω     55.00 173.00   1.00    6.26    --  107.08  15.00 -30.00  118
 11  ω     51.00  83.00   1.00    6.26    --  107.08 -30.00  30.00   32
 12  ω     92.00 135.00   1.00    6.26    --  107.08 -30.00  30.00   43
 13  ω    131.00 176.00   1.00    6.26    --  107.08  77.00-150.00   45
 14  ω     40.00  80.00   1.00    6.26    --  107.08 -61.00 -60.00   40
 15  ω     90.00 116.00   1.00    6.26    --  107.08  77.00-150.00   26
 16  ω     68.00 120.00   1.00    6.26    --  107.08-125.00 150.00   52
 17  ω     33.00 140.00   1.00    6.26    --  107.08 -77.00 120.00  107
 18  ω     33.00  60.00   1.00    6.26    --  107.08 -77.00 -60.00   27
;
_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      -0.2194838000
_diffrn_orient_matrix_UB_12      0.0073586000
_diffrn_orient_matrix_UB_13      0.0051621000
_diffrn_orient_matrix_UB_21      -0.0047069000
_diffrn_orient_matrix_UB_22      0.0013441000
_diffrn_orient_matrix_UB_23      -0.1116445000
_diffrn_orient_matrix_UB_31      0.0566322000
_diffrn_orient_matrix_UB_32      -0.1487407000
_diffrn_orient_matrix_UB_33      0.0151224000
_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                3137
_reflns_number_total             3633
_reflns_odcompleteness_completeness 99.92
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (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         0.729
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         3633
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.122
_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)+(0.0573P)²+0.3012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1144
_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. Restrained distances
 O4-C24
 1.42 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(O4) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.002
4. Others
 Fixed Sof: H24(0.5) O4(0.5) H4(0.5)
5.a Riding coordinates:
 O4(H4)
5.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)
5.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 0.02243(15) Uani 1 2 d S T P . .
O1 O 0.6741(2) 0.83119(14) -0.02359(11) 0.0268(4) Uani 1 1 d . . . . .
O2 O 0.9021(3) 0.81175(16) 0.08986(15) 0.0402(4) Uani 1 1 d . . . . .
O3 O 0.2058(3) 0.93531(15) 0.93607(11) 0.0295(4) Uani 1 1 d . . . . .
H3 H 0.1524 1.0136 0.9270 0.044 Uiso 1 1 calc GR . . . .
N1 N 0.2867(3) 0.62106(16) 0.40703(13) 0.0201(4) Uani 1 1 d . . . . .
N2 N 0.4287(3) 0.92374(16) 0.13068(12) 0.0208(4) Uani 1 1 d . . . . .
N3 N 0.2443(3) 0.16694(18) 0.46102(16) 0.0297(4) Uani 1 1 d . . . . .
C1 C 0.2414(3) 0.7257(2) 0.58311(16) 0.0202(4) Uani 1 1 d . . . . .
C2 C 0.2728(3) 0.79722(19) 0.49522(15) 0.0200(4) Uani 1 1 d . . . . .
H2 H 0.2782 0.8813 0.4939 0.024 Uiso 1 1 calc R . . . .
C3 C 0.2961(3) 0.74096(19) 0.40955(16) 0.0197(4) Uani 1 1 d . . . . .
C4 C 0.2542(3) 0.5522(2) 0.49053(15) 0.0198(4) Uani 1 1 d . . . . .
C5 C 0.2333(3) 0.6005(2) 0.58000(16) 0.0216(4) Uani 1 1 d . . . . .
H5 H 0.2142 0.5494 0.6372 0.026 Uiso 1 1 calc R . . . .
C6 C 0.3409(3) 0.8080(2) 0.31360(15) 0.0201(4) Uani 1 1 d . . . . .
C7 C 0.3658(3) 0.9309(2) 0.30174(15) 0.0212(4) Uani 1 1 d . . . . .
H7 H 0.3539 0.9761 0.3548 0.025 Uiso 1 1 calc R . . . .
C8 C 0.4085(3) 0.98442(19) 0.20975(16) 0.0212(4) Uani 1 1 d . . . . .
H8 H 0.4239 1.0666 0.2024 0.025 Uiso 1 1 calc R . . . .
C9 C 0.4038(4) 0.8057(2) 0.14206(17) 0.0296(5) Uani 1 1 d . . . . .
H9 H 0.4162 0.7627 0.0877 0.036 Uiso 1 1 calc R . . . .
C10 C 0.3608(4) 0.7458(2) 0.23103(17) 0.0274(5) Uani 1 1 d . . . . .
H10 H 0.3450 0.6639 0.2360 0.033 Uiso 1 1 calc R . . . .
C11 C 0.2455(3) 0.4199(2) 0.48187(16) 0.0208(4) Uani 1 1 d . . . . .
C12 C 0.2246(3) 0.3324(2) 0.56211(16) 0.0236(4) Uani 1 1 d . . . . .
H12 H 0.2097 0.3562 0.6246 0.028 Uiso 1 1 calc R . . . .
C13 C 0.2261(3) 0.2090(2) 0.54805(18) 0.0274(5) Uani 1 1 d . . . . .
H13 H 0.2137 0.1518 0.6029 0.033 Uiso 1 1 calc R . . . .
C14 C 0.2590(4) 0.2531(2) 0.38418(18) 0.0299(5) Uani 1 1 d . . . . .
H14 H 0.2694 0.2274 0.3224 0.036 Uiso 1 1 calc R . . . .
C15 C 0.2596(3) 0.3779(2) 0.39036(17) 0.0254(5) Uani 1 1 d . . . . .
H15 H 0.2694 0.4335 0.3340 0.031 Uiso 1 1 calc R . . . .
C16 C 0.2226(3) 0.7800(2) 0.67639(15) 0.0208(4) Uani 1 1 d . . . . .
C17 C 0.1372(3) 0.9117(2) 0.67851(16) 0.0228(4) Uani 1 1 d . . . . .
H17 H 0.0857 0.9652 0.6210 0.027 Uiso 1 1 calc R . . . .
C18 C 0.1273(3) 0.9649(2) 0.76472(17) 0.0244(5) Uani 1 1 d . . . . .
H18 H 0.0688 1.0531 0.7645 0.029 Uiso 1 1 calc R . . . .
C19 C 0.2048(3) 0.8864(2) 0.85140(16) 0.0230(4) Uani 1 1 d . . . . .
C20 C 0.2859(4) 0.7541(2) 0.85122(17) 0.0285(5) Uani 1 1 d . . . . .
H20 H 0.3344 0.7005 0.9091 0.034 Uiso 1 1 calc R . . . .
C21 C 0.2945(4) 0.7017(2) 0.76489(16) 0.0263(5) Uani 1 1 d . . . . .
H21 H 0.3490 0.6130 0.7657 0.032 Uiso 1 1 calc R . . . .
C22 C 0.8255(4) 0.7679(2) 0.02805(17) 0.0280(5) Uani 1 1 d . . . . .
C23 C 0.9158(4) 0.6292(2) 0.01330(17) 0.0273(5) Uani 1 1 d . . . . .
C24 C 1.0702(4) 0.5489(2) 0.0730(2) 0.0393(6) Uani 1 1 d D . . . .
H24 H 1.1176 0.5815 0.1224 0.047 Uiso 0.5 1 calc R . . A 2
C25 C 0.8461(4) 0.5787(2) -0.0598(2) 0.0366(6) Uani 1 1 d . . . . .
H25 H 0.7426 0.6311 -0.1001 0.044 Uiso 1 1 calc R . . . .
O4 O 1.1402(8) 0.5888(5) 0.1445(4) 0.0629(12) Uani 0.5 1 d D U . B 1
H4 H 1.0375 0.6392 0.1663 0.094 Uiso 0.5 1 d R . . 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 1.9584(14) 2_675 ?
Cu1 O1 1.9584(14) . ?
Cu1 N2 1.9917(17) 2_675 ?
Cu1 N2 1.9917(17) . ?
O1 C22 1.270(3) . ?
O2 C22 1.250(3) . ?
O3 H3 0.8200 . ?
O3 C19 1.355(3) . ?
N1 C3 1.340(3) . ?
N1 C4 1.336(3) . ?
N2 C8 1.340(3) . ?
N2 C9 1.343(3) . ?
N3 C13 1.336(3) . ?
N3 C14 1.338(3) . ?
C1 C2 1.395(3) . ?
C1 C5 1.396(3) . ?
C1 C16 1.480(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.393(3) . ?
C3 C6 1.492(3) . ?
C4 C5 1.399(3) . ?
C4 C11 1.490(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.395(3) . ?
C6 C10 1.392(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.383(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.376(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(3) . ?
C11 C15 1.396(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.383(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.391(3) . ?
C16 C21 1.403(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.393(3) . ?
C19 C20 1.391(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.387(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.503(3) . ?
C23 C24 1.391(4) . ?
C23 C25 1.389(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.381(3) 2_765 ?
C24 O4 1.304(5) . ?
C25 C24 1.381(3) 2_765 ?
C25 H25 0.9300 . ?
O4 H4 0.8500 . ?

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 90.93(7) 2_675 2_675 ?
O1 Cu1 N2 89.07(7) . 2_675 ?
O1 Cu1 N2 89.07(7) 2_675 . ?
O1 Cu1 N2 90.93(7) . . ?
N2 Cu1 N2 180.0 2_675 . ?
C22 O1 Cu1 124.06(14) . . ?
C19 O3 H3 109.5 . . ?
C4 N1 C3 118.51(18) . . ?
C8 N2 Cu1 122.56(14) . . ?
C8 N2 C9 117.74(18) . . ?
C9 N2 Cu1 119.68(14) . . ?
C13 N3 C14 115.65(19) . . ?
C2 C1 C5 117.59(19) . . ?
C2 C1 C16 120.92(18) . . ?
C5 C1 C16 121.47(19) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.10(18) . . ?
C3 C2 H2 120.4 . . ?
N1 C3 C2 122.95(19) . . ?
N1 C3 C6 114.51(18) . . ?
C2 C3 C6 122.50(18) . . ?
N1 C4 C5 122.13(19) . . ?
N1 C4 C11 115.38(18) . . ?
C5 C4 C11 122.48(19) . . ?
C1 C5 C4 119.70(19) . . ?
C1 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C7 C6 C3 123.35(19) . . ?
C10 C6 C3 119.16(18) . . ?
C10 C6 C7 117.48(19) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 118.94(19) . . ?
C8 C7 H7 120.5 . . ?
N2 C8 C7 123.29(19) . . ?
N2 C8 H8 118.4 . . ?
C7 C8 H8 118.4 . . ?
N2 C9 H9 118.7 . . ?
N2 C9 C10 122.6(2) . . ?
C10 C9 H9 118.7 . . ?
C6 C10 H10 120.0 . . ?
C9 C10 C6 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C4 123.07(19) . . ?
C12 C11 C15 116.61(19) . . ?
C15 C11 C4 120.31(19) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.4(2) . . ?
C13 C12 H12 120.3 . . ?
N3 C13 C12 124.4(2) . . ?
N3 C13 H13 117.8 . . ?
C12 C13 H13 117.8 . . ?
N3 C14 H14 117.8 . . ?
N3 C14 C15 124.4(2) . . ?
C15 C14 H14 117.8 . . ?
C11 C15 H15 120.3 . . ?
C14 C15 C11 119.5(2) . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C1 120.79(19) . . ?
C17 C16 C21 117.78(19) . . ?
C21 C16 C1 121.41(19) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.4(2) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.13(19) . . ?
C19 C18 H18 119.9 . . ?
O3 C19 C18 121.97(19) . . ?
O3 C19 C20 118.8(2) . . ?
C20 C19 C18 119.3(2) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 H21 119.4 . . ?
C20 C21 C16 121.2(2) . . ?
C20 C21 H21 119.4 . . ?
O1 C22 C23 116.4(2) . . ?
O2 C22 O1 125.2(2) . . ?
O2 C22 C23 118.4(2) . . ?
C24 C23 C22 120.5(2) . . ?
C25 C23 C22 120.6(2) . . ?
C25 C23 C24 118.8(2) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.8(2) 2_765 . ?
C25 C24 H24 119.6 2_765 . ?
O4 C24 C23 122.2(3) . . ?
O4 C24 C25 117.0(3) . 2_765 ?
C23 C25 H25 119.8 . . ?
C24 C25 C23 120.4(2) 2_765 . ?
C24 C25 H25 119.8 2_765 . ?
C24 O4 H4 102.4 . . ?

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 -12.1(3) . . . . ?
Cu1 O1 C22 C23 167.16(15) . . . . ?
Cu1 N2 C8 C7 -177.65(16) . . . . ?
Cu1 N2 C9 C10 177.84(19) . . . . ?
O1 C22 C23 C24 -173.8(2) . . . . ?
O1 C22 C23 C25 5.9(4) . . . . ?
O2 C22 C23 C24 5.5(4) . . . . ?
O2 C22 C23 C25 -174.8(2) . . . . ?
O3 C19 C20 C21 -177.3(2) . . . . ?
N1 C3 C6 C7 -177.0(2) . . . . ?
N1 C3 C6 C10 2.5(3) . . . . ?
N1 C4 C5 C1 1.6(3) . . . . ?
N1 C4 C11 C12 176.08(19) . . . . ?
N1 C4 C11 C15 -3.5(3) . . . . ?
N2 C9 C10 C6 0.2(4) . . . . ?
N3 C14 C15 C11 0.4(4) . . . . ?
C1 C2 C3 N1 1.1(3) . . . . ?
C1 C2 C3 C6 -176.65(19) . . . . ?
C1 C16 C17 C18 -176.8(2) . . . . ?
C1 C16 C21 C20 176.6(2) . . . . ?
C2 C1 C5 C4 -0.8(3) . . . . ?
C2 C1 C16 C17 33.1(3) . . . . ?
C2 C1 C16 C21 -145.1(2) . . . . ?
C2 C3 C6 C7 0.9(3) . . . . ?
C2 C3 C6 C10 -179.6(2) . . . . ?
C3 N1 C4 C5 -1.1(3) . . . . ?
C3 N1 C4 C11 179.97(18) . . . . ?
C3 C6 C7 C8 179.52(19) . . . . ?
C3 C6 C10 C9 -179.4(2) . . . . ?
C4 N1 C3 C2 -0.3(3) . . . . ?
C4 N1 C3 C6 177.65(18) . . . . ?
C4 C11 C12 C13 -177.3(2) . . . . ?
C4 C11 C15 C14 177.5(2) . . . . ?
C5 C1 C2 C3 -0.5(3) . . . . ?
C5 C1 C16 C17 -148.5(2) . . . . ?
C5 C1 C16 C21 33.2(3) . . . . ?
C5 C4 C11 C12 -2.8(3) . . . . ?
C5 C4 C11 C15 177.5(2) . . . . ?
C6 C7 C8 N2 -0.4(3) . . . . ?
C7 C6 C10 C9 0.1(3) . . . . ?
C8 N2 C9 C10 -0.6(4) . . . . ?
C9 N2 C8 C7 0.7(3) . . . . ?
C10 C6 C7 C8 0.0(3) . . . . ?
C11 C4 C5 C1 -179.51(19) . . . . ?
C11 C12 C13 N3 -0.8(4) . . . . ?
C12 C11 C15 C14 -2.1(3) . . . . ?
C13 N3 C14 C15 1.1(4) . . . . ?
C14 N3 C13 C12 -0.9(3) . . . . ?
C15 C11 C12 C13 2.3(3) . . . . ?
C16 C1 C2 C3 177.91(19) . . . . ?
C16 C1 C5 C4 -179.20(19) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
C17 C16 C21 C20 -1.7(3) . . . . ?
C17 C18 C19 O3 177.0(2) . . . . ?
C17 C18 C19 C20 -2.2(3) . . . . ?
C18 C19 C20 C21 1.9(4) . . . . ?
C19 C20 C21 C16 0.0(4) . . . . ?
C21 C16 C17 C18 1.5(3) . . . . ?
C22 C23 C24 C25 -180.0(2) . . . 2_765 ?
C22 C23 C24 O4 1.2(5) . . . . ?
C22 C23 C25 C24 180.0(2) . . . 2_765 ?
C24 C23 C25 C24 -0.3(5) . . . 2_765 ?
C25 C23 C24 C25 0.3(5) . . . 2_765 ?
C25 C23 C24 O4 -178.5(4) . . . . ?

_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 4.411
_oxdiff_exptl_absorpt_empirical_full_min 0.632
####################################################################### 
# 
# 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_a180620a
_database_code_depnum_ccdc_archive 'CCDC 1957636'
loop_
_audit_author_name
_audit_author_address
'En-Cui Yang'
;Tianjin Normal University
China
;
_audit_update_record             
;
2019-10-05 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;
_audit_creation_date             2019-06-17
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C50 H33 Cu N7 O8'
_chemical_formula_sum            'C50 H33 Cu N7 O8'
_chemical_formula_weight         923.37
_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                   7.1161(8)
_cell_length_b                   10.8134(14)
_cell_length_c                   13.898(2)
_cell_angle_alpha                81.988(12)
_cell_angle_beta                 86.064(10)
_cell_angle_gamma                74.160(10)
_cell_volume                     1018.3(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2148
_cell_measurement_temperature    127(1)
_cell_measurement_theta_max      27.2380
_cell_measurement_theta_min      2.5990
_shelx_estimated_absorpt_T_max   0.888
_shelx_estimated_absorpt_T_min   0.878
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             475
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.1226
_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       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6857
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         2.313
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      127(1)
_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    -17.00  73.00   1.00   19.45    --   11.40  57.00  60.00   90
  2  ω    -79.00  14.00   1.00   19.45    --  -11.55 -57.00 120.00   93
  3  ω    -38.00  62.00   1.00   19.45    --  -11.55  57.00 -90.00  100
  4  ω      2.00  27.00   1.00   19.45    --  -11.55 -99.00-120.00   25
;
_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      0.0769524000
_diffrn_orient_matrix_UB_12      -0.0324381000
_diffrn_orient_matrix_UB_13      0.0317770000
_diffrn_orient_matrix_UB_21      0.0675888000
_diffrn_orient_matrix_UB_22      -0.0054610000
_diffrn_orient_matrix_UB_23      -0.0401555000
_diffrn_orient_matrix_UB_31      0.0160053000
_diffrn_orient_matrix_UB_32      0.0603455000
_diffrn_orient_matrix_UB_33      0.0060647000
_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                2581
_reflns_number_total             3584
_reflns_odcompleteness_completeness 99.90
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.971
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         3584
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1388
_refine_ls_R_factor_gt           0.0998
_refine_ls_restrained_S_all      1.203
_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)+(0.0317P)²+5.8203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1954
_refine_ls_wR_factor_ref         0.2115
_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. Uiso/Uaniso restraints and constraints
Uanis(C25) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C22)
\\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(N4) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.005
Uanis(N1) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
Uanis(C8) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O4) \\sim
Ueq, Uanis(O5) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of
0.004
3. Others
 Fixed Sof: H24(0.5) N4(0.5) O4(0.5) O5(0.5)
4.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)
4.b Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_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 0.0237(4) Uani 1 2 d S T P . .
O1 O 0.6704(7) 0.8281(4) -0.0229(4) 0.0319(13) Uani 1 1 d . . . . .
O2 O 0.8873(9) 0.8131(6) 0.0896(5) 0.0583(18) Uani 1 1 d . U . . .
O3 O 0.2146(7) 0.9334(4) 0.9290(4) 0.0283(12) Uani 1 1 d . U . . .
H3 H 0.1720 1.0125 0.9194 0.042 Uiso 1 1 calc GR . . . .
N1 N 0.2846(8) 0.6100(5) 0.4060(5) 0.0239(14) Uani 1 1 d . U . . .
N2 N 0.4116(7) 0.9233(5) 0.1280(4) 0.0164(12) Uani 1 1 d . U . . .
N3 N 0.2559(9) 0.1457(6) 0.4650(5) 0.0335(16) Uani 1 1 d . . . . .
C1 C 0.2342(11) 0.7169(6) 0.5808(6) 0.0261(17) Uani 1 1 d . . . . .
C2 C 0.2641(9) 0.7898(6) 0.4927(5) 0.0218(16) Uani 1 1 d . . . . .
H2 H 0.2667 0.8755 0.4913 0.026 Uiso 1 1 calc R . . . .
C3 C 0.2898(10) 0.7332(6) 0.4075(5) 0.0223(16) Uani 1 1 d . . . . .
C4 C 0.2551(10) 0.5395(6) 0.4904(5) 0.0240(17) Uani 1 1 d . . . . .
C5 C 0.2336(10) 0.5894(7) 0.5778(5) 0.0248(17) Uani 1 1 d . . . . .
H5 H 0.2186 0.5370 0.6353 0.030 Uiso 1 1 calc R . . . .
C6 C 0.3278(9) 0.8023(6) 0.3119(5) 0.0189(15) Uani 1 1 d . . . . .
C7 C 0.3771(9) 0.9199(6) 0.3011(5) 0.0221(16) Uani 1 1 d . . . . .
H7 H 0.3854 0.9594 0.3554 0.027 Uiso 1 1 calc R . . . .
C8 C 0.4138(9) 0.9774(6) 0.2086(5) 0.0171(15) Uani 1 1 d . U . . .
H8 H 0.4413 1.0575 0.2024 0.021 Uiso 1 1 calc R . . . .
C9 C 0.3614(9) 0.8104(6) 0.1385(5) 0.0194(15) Uani 1 1 d . . . . .
H9 H 0.3542 0.7729 0.0831 0.023 Uiso 1 1 calc R . . . .
C10 C 0.3209(10) 0.7491(6) 0.2267(5) 0.0227(16) Uani 1 1 d . . . . .
H10 H 0.2882 0.6709 0.2302 0.027 Uiso 1 1 calc R . . . .
C11 C 0.2531(10) 0.4040(7) 0.4830(6) 0.0260(17) Uani 1 1 d . . . . .
C12 C 0.2279(10) 0.3164(7) 0.5634(6) 0.0275(17) Uani 1 1 d . . . . .
H12 H 0.2082 0.3420 0.6253 0.033 Uiso 1 1 calc R . . . .
C13 C 0.2326(10) 0.1909(7) 0.5503(6) 0.0277(18) Uani 1 1 d . . . . .
H13 H 0.2183 0.1342 0.6054 0.033 Uiso 1 1 calc R . . . .
C14 C 0.2771(12) 0.2316(7) 0.3877(7) 0.039(2) Uani 1 1 d . . . . .
H14 H 0.2923 0.2044 0.3264 0.047 Uiso 1 1 calc R . . . .
C15 C 0.2776(11) 0.3578(7) 0.3943(6) 0.0325(19) Uani 1 1 d . . . . .
H15 H 0.2947 0.4121 0.3383 0.039 Uiso 1 1 calc R . . . .
C16 C 0.2164(11) 0.7722(7) 0.6736(6) 0.0268(17) Uani 1 1 d . . . . .
C17 C 0.1198(10) 0.9019(7) 0.6800(6) 0.0251(17) Uani 1 1 d . . . . .
H17 H 0.0569 0.9528 0.6259 0.030 Uiso 1 1 calc R . . . .
C18 C 0.1149(10) 0.9572(6) 0.7647(5) 0.0230(16) Uani 1 1 d . . . . .
H18 H 0.0498 1.0440 0.7671 0.028 Uiso 1 1 calc R . . . .
C19 C 0.2075(10) 0.8822(6) 0.8455(5) 0.0218(16) Uani 1 1 d . . . . .
C20 C 0.2986(10) 0.7512(7) 0.8424(6) 0.0285(18) Uani 1 1 d . . . . .
H20 H 0.3579 0.7000 0.8973 0.034 Uiso 1 1 calc R . . . .
C21 C 0.3006(11) 0.6974(7) 0.7574(6) 0.0277(18) Uani 1 1 d . . . . .
H21 H 0.3593 0.6095 0.7562 0.033 Uiso 1 1 calc R . . . .
C22 C 0.8146(11) 0.7693(7) 0.0284(6) 0.0328(19) Uani 1 1 d . U . . .
C23 C 0.9053(11) 0.6286(7) 0.0132(7) 0.0331(19) Uani 1 1 d . U . . .
C24 C 0.9847(12) 0.5374(8) 0.0878(7) 0.043(2) Uani 1 1 d . U . . .
H24 H 0.9724 0.5617 0.1500 0.052 Uiso 0.5 1 calc R . . A 2
C25 C 0.9169(12) 0.5901(8) -0.0760(7) 0.043(2) Uani 1 1 d . U . . .
H25 H 0.8600 0.6479 -0.1287 0.051 Uiso 1 1 calc R . . . .
N4 N 0.9391(18) 0.5650(11) 0.1740(9) 0.026(3) Uani 0.5 1 d . U . B 1
O4 O 0.7711(16) 0.6271(10) 0.1972(9) 0.042(3) Uani 0.5 1 d . U . B 1
O5 O 1.0701(16) 0.5283(10) 0.2308(9) 0.043(3) Uani 0.5 1 d . U . 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 1.977(5) 2_675 ?
Cu1 O1 1.977(5) . ?
Cu1 N2 1.992(5) . ?
Cu1 N2 1.992(6) 2_675 ?
O1 C22 1.259(9) . ?
O2 C22 1.233(10) . ?
O3 C19 1.364(8) . ?
N1 C3 1.347(8) . ?
N1 C4 1.344(9) . ?
N2 C8 1.337(8) . ?
N2 C9 1.349(8) . ?
N3 C13 1.327(10) . ?
N3 C14 1.348(10) . ?
C1 C2 1.396(10) . ?
C1 C5 1.387(9) . ?
C1 C16 1.480(10) . ?
C2 C3 1.386(10) . ?
C3 C6 1.477(10) . ?
C4 C5 1.380(10) . ?
C4 C11 1.487(9) . ?
C6 C7 1.394(9) . ?
C6 C10 1.397(10) . ?
C7 C8 1.388(9) . ?
C9 C10 1.363(10) . ?
C11 C12 1.396(10) . ?
C11 C15 1.376(10) . ?
C12 C13 1.385(10) . ?
C14 C15 1.382(10) . ?
C16 C17 1.396(9) . ?
C16 C21 1.392(10) . ?
C17 C18 1.387(10) . ?
C18 C19 1.382(10) . ?
C19 C20 1.393(9) . ?
C20 C21 1.386(10) . ?
C22 C23 1.520(10) . ?
C23 C24 1.363(11) . ?
C23 C25 1.352(12) . ?
C24 C25 1.393(11) 2_765 ?
C24 N4 1.273(15) . ?
C25 C24 1.393(11) 2_765 ?
N4 O4 1.246(15) . ?
N4 O5 1.209(15) . ?

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 89.9(2) . 2_675 ?
O1 Cu1 N2 90.1(2) 2_675 2_675 ?
O1 Cu1 N2 89.9(2) 2_675 . ?
O1 Cu1 N2 90.1(2) . . ?
N2 Cu1 N2 180.0 . 2_675 ?
C22 O1 Cu1 122.8(5) . . ?
C4 N1 C3 118.5(6) . . ?
C8 N2 Cu1 120.8(4) . . ?
C8 N2 C9 117.2(6) . . ?
C9 N2 Cu1 121.8(5) . . ?
C13 N3 C14 115.2(7) . . ?
C2 C1 C16 120.8(6) . . ?
C5 C1 C2 117.3(7) . . ?
C5 C1 C16 121.8(7) . . ?
C3 C2 C1 119.5(6) . . ?
N1 C3 C2 122.3(7) . . ?
N1 C3 C6 114.8(6) . . ?
C2 C3 C6 122.8(6) . . ?
N1 C4 C5 121.8(6) . . ?
N1 C4 C11 115.5(6) . . ?
C5 C4 C11 122.8(7) . . ?
C4 C5 C1 120.6(7) . . ?
C7 C6 C3 123.1(6) . . ?
C7 C6 C10 116.5(6) . . ?
C10 C6 C3 120.4(6) . . ?
C8 C7 C6 119.4(7) . . ?
N2 C8 C7 123.3(6) . . ?
N2 C9 C10 122.9(6) . . ?
C9 C10 C6 120.7(6) . . ?
C12 C11 C4 123.2(7) . . ?
C15 C11 C4 120.8(7) . . ?
C15 C11 C12 116.0(7) . . ?
C13 C12 C11 119.5(7) . . ?
N3 C13 C12 124.9(7) . . ?
N3 C14 C15 123.7(8) . . ?
C11 C15 C14 120.7(8) . . ?
C17 C16 C1 121.5(7) . . ?
C21 C16 C1 121.1(6) . . ?
C21 C16 C17 117.5(7) . . ?
C18 C17 C16 121.9(7) . . ?
C19 C18 C17 119.3(6) . . ?
O3 C19 C18 121.6(6) . . ?
O3 C19 C20 118.4(6) . . ?
C18 C19 C20 120.0(7) . . ?
C21 C20 C19 119.8(7) . . ?
C20 C21 C16 121.4(6) . . ?
O1 C22 C23 115.5(7) . . ?
O2 C22 O1 127.1(7) . . ?
O2 C22 C23 117.3(7) . . ?
C24 C23 C22 121.5(8) . . ?
C25 C23 C22 121.1(8) . . ?
C25 C23 C24 117.3(7) . . ?
C23 C24 C25 123.6(9) . 2_765 ?
N4 C24 C23 117.4(9) . . ?
N4 C24 C25 117.9(10) . 2_765 ?
C23 C25 C24 119.0(8) . 2_765 ?
O4 N4 C24 121.8(12) . . ?
O5 N4 C24 115.5(12) . . ?
O5 N4 O4 122.7(13) . . ?

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 -10.5(12) . . . . ?
Cu1 O1 C22 C23 168.8(5) . . . . ?
Cu1 N2 C8 C7 -171.8(5) . . . . ?
Cu1 N2 C9 C10 172.7(5) . . . . ?
O1 C22 C23 C24 -146.2(8) . . . . ?
O1 C22 C23 C25 36.3(11) . . . . ?
O2 C22 C23 C24 33.2(11) . . . . ?
O2 C22 C23 C25 -144.4(8) . . . . ?
O3 C19 C20 C21 -177.5(7) . . . . ?
N1 C3 C6 C7 -166.8(6) . . . . ?
N1 C3 C6 C10 11.4(9) . . . . ?
N1 C4 C5 C1 2.5(11) . . . . ?
N1 C4 C11 C12 178.9(6) . . . . ?
N1 C4 C11 C15 -0.8(10) . . . . ?
N2 C9 C10 C6 0.7(10) . . . . ?
N3 C14 C15 C11 -0.9(13) . . . . ?
C1 C2 C3 N1 0.9(10) . . . . ?
C1 C2 C3 C6 -178.2(6) . . . . ?
C1 C16 C17 C18 -175.0(7) . . . . ?
C1 C16 C21 C20 174.5(7) . . . . ?
C2 C1 C5 C4 -2.2(11) . . . . ?
C2 C1 C16 C17 37.4(11) . . . . ?
C2 C1 C16 C21 -140.7(7) . . . . ?
C2 C3 C6 C7 12.4(10) . . . . ?
C2 C3 C6 C10 -169.5(7) . . . . ?
C3 N1 C4 C5 -1.1(10) . . . . ?
C3 N1 C4 C11 -179.4(6) . . . . ?
C3 C6 C7 C8 178.9(6) . . . . ?
C3 C6 C10 C9 -178.1(6) . . . . ?
C4 N1 C3 C2 -0.7(10) . . . . ?
C4 N1 C3 C6 178.5(6) . . . . ?
C4 C11 C12 C13 -178.5(7) . . . . ?
C4 C11 C15 C14 179.5(7) . . . . ?
C5 C1 C2 C3 0.5(10) . . . . ?
C5 C1 C16 C17 -146.4(7) . . . . ?
C5 C1 C16 C21 35.5(11) . . . . ?
C5 C4 C11 C12 0.5(11) . . . . ?
C5 C4 C11 C15 -179.2(7) . . . . ?
C6 C7 C8 N2 -2.6(10) . . . . ?
C7 C6 C10 C9 0.2(10) . . . . ?
C8 N2 C9 C10 -2.4(9) . . . . ?
C9 N2 C8 C7 3.4(9) . . . . ?
C10 C6 C7 C8 0.7(9) . . . . ?
C11 C4 C5 C1 -179.2(7) . . . . ?
C11 C12 C13 N3 -1.4(11) . . . . ?
C12 C11 C15 C14 -0.2(11) . . . . ?
C13 N3 C14 C15 0.8(12) . . . . ?
C14 N3 C13 C12 0.4(11) . . . . ?
C15 C11 C12 C13 1.2(10) . . . . ?
C16 C1 C2 C3 176.8(7) . . . . ?
C16 C1 C5 C4 -178.5(7) . . . . ?
C16 C17 C18 C19 -0.2(11) . . . . ?
C17 C16 C21 C20 -3.7(11) . . . . ?
C17 C18 C19 O3 176.9(6) . . . . ?
C17 C18 C19 C20 -2.3(10) . . . . ?
C18 C19 C20 C21 1.8(11) . . . . ?
C19 C20 C21 C16 1.3(11) . . . . ?
C21 C16 C17 C18 3.1(11) . . . . ?
C22 C23 C24 C25 -174.7(7) . . . 2_765 ?
C22 C23 C24 N4 16.9(13) . . . . ?
C22 C23 C25 C24 174.9(7) . . . 2_765 ?
C23 C24 N4 O4 37.9(16) . . . . ?
C23 C24 N4 O5 -141.2(11) . . . . ?
C24 C23 C25 C24 -2.8(13) . . . 2_765 ?
C25 C23 C24 C25 2.9(14) . . . 2_765 ?
C25 C23 C24 N4 -165.5(9) . . . . ?
C25 C24 N4 O4 -131.1(12) 2_765 . . . ?
C25 C24 N4 O5 49.7(15) 2_765 . . . ?

_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 2.057
_oxdiff_exptl_absorpt_empirical_full_min 0.609
####################################################################### 
# 
# 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_n180327a
_database_code_depnum_ccdc_archive 'CCDC 1957637'
loop_
_audit_author_name
_audit_author_address
'En-Cui Yang'
;Tianjin Normal University
China
;
_audit_update_record             
;
2019-10-05 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;
_audit_creation_date             2019-06-17
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C50 H30 Br Cu N6 O6, 2(H)'
_chemical_formula_sum            'C50 H32 Br Cu N6 O6'
_chemical_formula_weight         956.26
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   7.2467(13)
_cell_length_b                   10.935(2)
_cell_length_c                   13.919(3)
_cell_angle_alpha                82.290(4)
_cell_angle_beta                 87.182(4)
_cell_angle_gamma                72.275(4)
_cell_volume                     1041.1(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.768
_shelx_estimated_absorpt_T_min   0.727
_exptl_absorpt_coefficient_mu    1.545
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0915 before and 0.0387 after correction.
The Ratio of minimum to maximum transmission is 0.8690.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             486
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0961
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6040
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.009
_diffrn_reflns_theta_max         25.009
_diffrn_reflns_theta_min         1.971
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2466
_reflns_number_total             3663
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.576
_refine_diff_density_min         -1.448
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3663
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1339
_refine_ls_R_factor_gt           0.0911
_refine_ls_restrained_S_all      1.072
_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)+(0.1103P)²+4.3466P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2312
_refine_ls_wR_factor_ref         0.2565
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H) groups, H of C23, HA of C23'
 At 1.2 times of:
  H14 of C14, H21 of C21, H10 of C10, H9 of C9, H8 of C8, H25 of C25, H25' of
  C25', H17 of C17, H18 of C18, H15 of C15, H13 of C13, H12 of C12, H7 of C7,
  H5 of C5, H2 of C2
2. Restrained distances
 C23-Br1
 1.65 with sigma of 0.01
 C23-C24 = C24-C25
 1.38 with sigma of 0.01
 C23-C25
 2.37 with sigma of 0.01
 C23'-Br1'
 1.65 with sigma of 0.01
 C23'-C24 = C24-C25'
 1.38 with sigma of 0.01
 C23'-C25'
 2.37 with sigma of 0.01
3. Restrained planarity
 C23, C24, C25, Br1, C22
 with sigma of 0.001
 C23', C24, C25', Br1', C22
 with sigma of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(Br1) = Uanis(Br1')
Uanis(C25) = Uanis(C25')
Uanis(C23) = Uanis(C23')
5. Others
 Fixed Sof: Br1(0.4) C25(0.8) H25(0.8) C23(0.8) H(0.8) Br1'(0.1) C25'(0.2)
 H25'(0.2) C23'(0.2) HA(0.2)
6.a Riding coordinates:
 O3(H3), C23(H), C23'(HA)
6.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), C21(H21), C25(H25), C25'(H25')
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.0359(4) Uani 1 2 d S T P . .
O1 O 0.6716(8) 0.8297(4) -0.0221(4) 0.0481(15) Uani 1 1 d . . . . .
O3 O 0.2115(9) 0.9338(5) 0.9292(4) 0.0531(15) Uani 1 1 d . . . . .
H3 H 0.1706 1.0131 0.9209 0.080 Uiso 1 1 d R . . . .
N1 N 0.2840(8) 0.6192(5) 0.4012(4) 0.0306(13) Uani 1 1 d . . . . .
N2 N 0.4188(8) 0.9237(5) 0.1276(4) 0.0342(14) Uani 1 1 d . . . . .
N3 N 0.2497(9) 0.1625(6) 0.4626(6) 0.0469(17) Uani 1 1 d . . . . .
C1 C 0.2391(9) 0.7266(6) 0.5765(5) 0.0287(15) Uani 1 1 d . . . . .
C2 C 0.2670(9) 0.7967(6) 0.4897(5) 0.0283(15) Uani 1 1 d . . . . .
H2 H 0.2690 0.8816 0.4884 0.034 Uiso 1 1 calc R . . . .
C3 C 0.2922(9) 0.7398(6) 0.4042(5) 0.0262(14) Uani 1 1 d . . . . .
C4 C 0.2554(9) 0.5508(6) 0.4858(5) 0.0286(15) Uani 1 1 d . . . . .
C5 C 0.2336(9) 0.6008(6) 0.5731(5) 0.0314(15) Uani 1 1 d . . . . .
H5 H 0.2151 0.5504 0.6299 0.038 Uiso 1 1 calc R . . . .
C6 C 0.3327(9) 0.8056(6) 0.3103(5) 0.0295(15) Uani 1 1 d . . . . .
C7 C 0.3651(9) 0.9272(6) 0.2978(5) 0.0309(15) Uani 1 1 d . . . . .
H7 H 0.3592 0.9713 0.3511 0.037 Uiso 1 1 calc R . . . .
C8 C 0.4052(10) 0.9810(6) 0.2080(5) 0.0332(16) Uani 1 1 d . . . . .
H8 H 0.4242 1.0620 0.2023 0.040 Uiso 1 1 calc R . . . .
C9 C 0.3870(12) 0.8072(7) 0.1382(6) 0.046(2) Uani 1 1 d . . . . .
H9 H 0.3932 0.7659 0.0834 0.055 Uiso 1 1 calc R . . . .
C10 C 0.3460(12) 0.7467(7) 0.2257(6) 0.0443(19) Uani 1 1 d . . . . .
H10 H 0.3268 0.6659 0.2290 0.053 Uiso 1 1 calc R . . . .
C11 C 0.2518(9) 0.4163(6) 0.4784(5) 0.0306(16) Uani 1 1 d . . . . .
C12 C 0.2316(10) 0.3316(7) 0.5596(6) 0.0376(17) Uani 1 1 d . . . . .
H12 H 0.2191 0.3574 0.6212 0.045 Uiso 1 1 calc R . . . .
C13 C 0.2303(10) 0.2090(7) 0.5470(6) 0.0419(18) Uani 1 1 d . . . . .
H13 H 0.2147 0.1545 0.6021 0.050 Uiso 1 1 calc R . . . .
C14 C 0.2663(13) 0.2451(8) 0.3864(7) 0.053(2) Uani 1 1 d . . . . .
H14 H 0.2789 0.2164 0.3257 0.064 Uiso 1 1 calc R . . . .
C15 C 0.2665(11) 0.3708(7) 0.3902(6) 0.0414(18) Uani 1 1 d . . . . .
H15 H 0.2764 0.4241 0.3335 0.050 Uiso 1 1 calc R . . . .
C16 C 0.2225(9) 0.7820(6) 0.6695(5) 0.0312(15) Uani 1 1 d . . . . .
C17 C 0.1419(11) 0.9120(7) 0.6748(6) 0.0395(18) Uani 1 1 d . . . . .
H17 H 0.0902 0.9661 0.6189 0.047 Uiso 1 1 calc R . . . .
C18 C 0.1346(10) 0.9658(7) 0.7603(6) 0.0379(17) Uani 1 1 d . . . . .
H18 H 0.0803 1.0544 0.7612 0.045 Uiso 1 1 calc R . . . .
C19 C 0.2082(10) 0.8870(7) 0.8435(5) 0.0372(17) Uani 1 1 d . . . . .
C20 C 0.2909(13) 0.7530(7) 0.8426(6) 0.051(2) Uani 1 1 d . . . . .
C21 C 0.2956(13) 0.7033(7) 0.7552(6) 0.049(2) Uani 1 1 d . . . . .
H21 H 0.3492 0.6147 0.7538 0.059 Uiso 1 1 calc R . . . .
Br1 Br 0.9843(6) 0.5814(3) 0.2031(2) 0.1027(12) Uani 0.4 1 d D . . A 1
O2 O 0.8913(10) 0.8148(6) 0.0870(7) 0.092(3) Uani 1 1 d . . . . .
C24 C 0.9100(5) 0.6286(5) 0.0144(4) 0.047(2) Uani 1 1 d D . . . .
C22 C 0.8177(11) 0.7706(7) 0.0280(6) 0.047(2) Uani 1 1 d . . . . .
C25 C 0.9157(9) 0.5898(8) -0.0759(5) 0.053(3) Uani 0.8 1 d D . . B 1
H25 H 0.8547 0.6496 -0.1273 0.063 Uiso 0.8 1 calc R . . B 1
C23 C 0.9886(8) 0.5377(8) 0.0921(5) 0.063(3) Uani 0.8 1 d D . . A 1
H H 1.0041 0.5656 0.1527 0.094 Uiso 0.8 1 d R . . A 3
Br1' Br 0.6193(17) 0.6338(12) -0.1146(8) 0.1027(12) Uani 0.1 1 d D . . B 2
C25' C 1.0769(12) 0.5522(19) 0.0598(8) 0.053(3) Uani 0.2 1 d D . . B 2
H25' H 1.1271 0.5897 0.1043 0.063 Uiso 0.2 1 calc R . . B 2
C23' C 0.8182(17) 0.5768(16) -0.0472(6) 0.063(3) Uani 0.2 1 d D . . B 2
HA H 0.7057 0.6279 -0.0817 0.094 Uiso 0.2 1 d R . . B 4


_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 1.953(4) 2_675 ?
Cu1 O1 1.953(4) . ?
Cu1 N2 1.998(6) . ?
Cu1 N2 1.998(6) 2_675 ?
O1 C22 1.249(9) . ?
O3 H3 0.8199 . ?
O3 C19 1.364(9) . ?
N1 C3 1.345(8) . ?
N1 C4 1.351(9) . ?
N2 C8 1.340(9) . ?
N2 C9 1.350(9) . ?
N3 C13 1.327(10) . ?
N3 C14 1.324(11) . ?
C1 C2 1.382(9) . ?
C1 C5 1.395(9) . ?
C1 C16 1.486(10) . ?
C2 H2 0.9300 . ?
C2 C3 1.394(9) . ?
C3 C6 1.466(9) . ?
C4 C5 1.380(9) . ?
C4 C11 1.496(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.407(9) . ?
C6 C10 1.402(10) . ?
C7 H7 0.9300 . ?
C7 C8 1.366(10) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.370(11) . ?
C10 H10 0.9300 . ?
C11 C12 1.393(10) . ?
C11 C15 1.373(10) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(10) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.383(11) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(9) . ?
C16 C21 1.397(10) . ?
C17 H17 0.9300 . ?
C17 C18 1.389(10) . ?
C18 H18 0.9300 . ?
C18 C19 1.371(10) . ?
C19 C20 1.406(10) . ?
C20 C21 1.392(11) . ?
C20 Br1' 2.400(14) 1_556 ?
C21 H21 0.9300 . ?
Br1 C23 1.673(7) . ?
O2 C22 1.225(10) . ?
C24 C22 1.525(8) . ?
C24 C25 1.374(7) . ?
C24 C23 1.383(7) . ?
C24 C25' 1.371(9) . ?
C24 C23' 1.383(9) . ?
C25 H25 0.9300 . ?
C25 C23 1.399(11) 2_765 ?
C23 C25 1.399(11) 2_765 ?
Br1' C20 2.400(14) 1_554 ?
Br1' C23' 1.666(9) . ?
C25' H25' 0.9300 . ?
C25' C23' 1.41(2) 2_765 ?
C23' C25' 1.41(2) 2_765 ?

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 90.0(2) 2_675 . ?
O1 Cu1 N2 90.0(2) . 2_675 ?
O1 Cu1 N2 90.0(2) . . ?
O1 Cu1 N2 90.0(2) 2_675 2_675 ?
N2 Cu1 N2 180.0(3) 2_675 . ?
C22 O1 Cu1 123.3(5) . . ?
C19 O3 H3 109.5 . . ?
C3 N1 C4 117.5(6) . . ?
C8 N2 Cu1 122.0(5) . . ?
C8 N2 C9 116.5(6) . . ?
C9 N2 Cu1 121.4(5) . . ?
C14 N3 C13 114.9(7) . . ?
C2 C1 C5 117.1(6) . . ?
C2 C1 C16 121.0(6) . . ?
C5 C1 C16 121.8(6) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.8(6) . . ?
C3 C2 H2 120.1 . . ?
N1 C3 C2 122.8(6) . . ?
N1 C3 C6 114.3(6) . . ?
C2 C3 C6 122.9(6) . . ?
N1 C4 C5 122.4(6) . . ?
N1 C4 C11 115.2(6) . . ?
C5 C4 C11 122.4(6) . . ?
C1 C5 H5 119.8 . . ?
C4 C5 C1 120.4(6) . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C3 124.1(6) . . ?
C10 C6 C3 120.5(6) . . ?
C10 C6 C7 115.4(6) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.5(6) . . ?
C8 C7 H7 119.8 . . ?
N2 C8 C7 123.7(6) . . ?
N2 C8 H8 118.1 . . ?
C7 C8 H8 118.1 . . ?
N2 C9 H9 118.3 . . ?
N2 C9 C10 123.3(7) . . ?
C10 C9 H9 118.3 . . ?
C6 C10 H10 119.7 . . ?
C9 C10 C6 120.5(7) . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C4 122.2(7) . . ?
C15 C11 C4 121.1(6) . . ?
C15 C11 C12 116.7(6) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.9(7) . . ?
C13 C12 H12 120.6 . . ?
N3 C13 C12 125.2(7) . . ?
N3 C13 H13 117.4 . . ?
C12 C13 H13 117.4 . . ?
N3 C14 H14 117.6 . . ?
N3 C14 C15 124.9(8) . . ?
C15 C14 H14 117.6 . . ?
C11 C15 C14 119.5(7) . . ?
C11 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C1 122.0(7) . . ?
C17 C16 C21 117.2(7) . . ?
C21 C16 C1 120.7(6) . . ?
C16 C17 H17 118.7 . . ?
C16 C17 C18 122.5(7) . . ?
C18 C17 H17 118.7 . . ?
C17 C18 H18 120.3 . . ?
C19 C18 C17 119.4(6) . . ?
C19 C18 H18 120.3 . . ?
O3 C19 C18 122.4(6) . . ?
O3 C19 C20 116.9(7) . . ?
C18 C19 C20 120.6(7) . . ?
C19 C20 Br1' 124.9(7) . 1_556 ?
C21 C20 C19 118.1(7) . . ?
C21 C20 Br1' 95.4(6) . 1_556 ?
C16 C21 H21 118.9 . . ?
C20 C21 C16 122.2(7) . . ?
C20 C21 H21 118.9 . . ?
C25 C24 C22 120.0(6) . . ?
C25 C24 C23 119.2(6) . . ?
C23 C24 C22 120.7(6) . . ?
C25' C24 C22 123.1(10) . . ?
C25' C24 C23' 119.6(10) . . ?
C23' C24 C22 117.3(8) . . ?
O1 C22 C24 115.9(7) . . ?
O2 C22 O1 126.6(7) . . ?
O2 C22 C24 117.5(7) . . ?
C24 C25 H25 119.3 . . ?
C24 C25 C23 121.4(7) . 2_765 ?
C23 C25 H25 119.3 2_765 . ?
C24 C23 Br1 120.6(6) . . ?
C24 C23 C25 119.2(7) . 2_765 ?
C25 C23 Br1 120.1(6) 2_765 . ?
C23' Br1' C20 158.3(8) . 1_554 ?
C24 C25' H25' 116.1 . . ?
C24 C25' C23' 127.7(16) . 2_765 ?
C23' C25' H25' 116.1 2_765 . ?
C24 C23' Br1' 134.8(13) . . ?
C24 C23' C25' 112.5(12) . 2_765 ?
C25' C23' Br1' 112.6(10) 2_765 . ?

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(12) . . . . ?
Cu1 O1 C22 C24 167.8(4) . . . . ?
Cu1 N2 C8 C7 -174.7(5) . . . . ?
Cu1 N2 C9 C10 174.7(6) . . . . ?
O3 C19 C20 C21 -177.7(8) . . . . ?
O3 C19 C20 Br1' -57.6(10) . . . 1_556 ?
N1 C3 C6 C7 -174.0(6) . . . . ?
N1 C3 C6 C10 4.4(9) . . . . ?
N1 C4 C5 C1 0.4(10) . . . . ?
N1 C4 C11 C12 177.4(6) . . . . ?
N1 C4 C11 C15 -3.3(9) . . . . ?
N2 C9 C10 C6 0.8(13) . . . . ?
N3 C14 C15 C11 1.2(13) . . . . ?
C1 C2 C3 N1 2.4(10) . . . . ?
C1 C2 C3 C6 -176.7(6) . . . . ?
C1 C16 C17 C18 -176.6(7) . . . . ?
C1 C16 C21 C20 176.9(8) . . . . ?
C2 C1 C5 C4 0.0(9) . . . . ?
C2 C1 C16 C17 32.3(10) . . . . ?
C2 C1 C16 C21 -145.4(7) . . . . ?
C2 C3 C6 C7 5.2(10) . . . . ?
C2 C3 C6 C10 -176.4(6) . . . . ?
C3 N1 C4 C5 0.5(9) . . . . ?
C3 N1 C4 C11 -178.7(5) . . . . ?
C3 C6 C7 C8 178.9(6) . . . . ?
C3 C6 C10 C9 -178.9(7) . . . . ?
C4 N1 C3 C2 -1.9(9) . . . . ?
C4 N1 C3 C6 177.2(5) . . . . ?
C4 C11 C12 C13 -179.7(6) . . . . ?
C4 C11 C15 C14 178.7(7) . . . . ?
C5 C1 C2 C3 -1.3(9) . . . . ?
C5 C1 C16 C17 -149.9(7) . . . . ?
C5 C1 C16 C21 32.4(10) . . . . ?
C5 C4 C11 C12 -1.9(10) . . . . ?
C5 C4 C11 C15 177.5(6) . . . . ?
C6 C7 C8 N2 -0.8(11) . . . . ?
C7 C6 C10 C9 -0.4(11) . . . . ?
C8 N2 C9 C10 -1.1(11) . . . . ?
C9 N2 C8 C7 1.1(10) . . . . ?
C10 C6 C7 C8 0.4(10) . . . . ?
C11 C4 C5 C1 179.6(6) . . . . ?
C11 C12 C13 N3 1.0(11) . . . . ?
C12 C11 C15 C14 -1.9(11) . . . . ?
C13 N3 C14 C15 0.6(12) . . . . ?
C14 N3 C13 C12 -1.7(11) . . . . ?
C15 C11 C12 C13 0.9(10) . . . . ?
C16 C1 C2 C3 176.6(6) . . . . ?
C16 C1 C5 C4 -178.0(6) . . . . ?
C16 C17 C18 C19 -0.8(11) . . . . ?
C17 C16 C21 C20 -1.0(12) . . . . ?
C17 C18 C19 O3 177.8(7) . . . . ?
C17 C18 C19 C20 0.2(12) . . . . ?
C18 C19 C20 C21 0.0(13) . . . . ?
C18 C19 C20 Br1' 120.2(8) . . . 1_556 ?
C19 C20 C21 C16 0.4(13) . . . . ?
C20 Br1' C23' C24 -41(2) 1_554 . . . ?
C20 Br1' C23' C25' 143(2) 1_554 . . 2_765 ?
C21 C16 C17 C18 1.1(11) . . . . ?
C22 C24 C25 C23 175.4(8) . . . 2_765 ?
C22 C24 C23 Br1 0.01(4) . . . . ?
C22 C24 C23 C25 -175.5(8) . . . 2_765 ?
C22 C24 C25' C23' -175.0(10) . . . 2_765 ?
C22 C24 C23' Br1' 0.00(4) . . . . ?
C22 C24 C23' C25' 175.8(9) . . . 2_765 ?
C25 C24 C22 O1 36.6(6) . . . . ?
C25 C24 C22 O2 -144.2(7) . . . . ?
C25 C24 C23 Br1 -179.99(3) . . . . ?
C25 C24 C23 C25 4.5(8) . . . 2_765 ?
C23 C24 C22 O1 -143.4(6) . . . . ?
C23 C24 C22 O2 35.7(7) . . . . ?
C23 C24 C25 C23 -4.6(8) . . . 2_765 ?
Br1' C20 C21 C16 -134.2(8) 1_556 . . . ?
C25' C24 C22 O1 176.3(7) . . . . ?
C25' C24 C22 O2 -4.5(8) . . . . ?
C25' C24 C23' Br1' 180.00(3) . . . . ?
C25' C24 C23' C25' -4.2(9) . . . 2_765 ?
C23' C24 C22 O1 -3.7(7) . . . . ?
C23' C24 C22 O2 175.5(8) . . . . ?
C23' C24 C25' C23' 5.0(10) . . . 2_765 ?

_olex2_submission_special_instructions 'No special instructions were received'
