# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_20180930_czf_zyj_b4cuaaa
_database_code_depnum_ccdc_archive 'CCDC 2102153'
loop_
_audit_author_name
_audit_author_address
'Yunqiong Gu'
;Guangxi Normal University
China
;
_audit_update_record             
;
2021-08-09 deposited with the CCDC.	2021-12-08 downloaded from the CCDC.
;
_audit_creation_date             2021-07-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 Br Cl2 Cu N3 O, C H4 O'
_chemical_formula_sum            'C22 H18 Br Cl2 Cu N3 O2'
_chemical_formula_weight         570.74
_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 0.0030 0.0020 '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 -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3200 1.2650 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.5612(5)
_cell_length_b                   28.3386(12)
_cell_length_c                   7.3454(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.741(4)
_cell_angle_gamma                90
_cell_volume                     2178.37(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3608
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1290
_cell_measurement_theta_min      3.4690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull brownish colourless'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1140
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            11964
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.099
_diffrn_reflns_theta_min         3.473
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  90.00   1.00   60.00    --   17.54  38.00-120.00   93
  2  ω     58.00  94.00   1.00   60.00    --   17.54 178.00  90.00   36
  3  ω     36.00  87.00   1.00   60.00    --   17.54 178.00-180.00   51
  4  ω    -43.00  53.00   1.00   60.00    --  -19.80  38.00 -30.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0375232000
_diffrn_orient_matrix_UB_12      -0.0158783000
_diffrn_orient_matrix_UB_13      0.0594087000
_diffrn_orient_matrix_UB_21      0.0533382000
_diffrn_orient_matrix_UB_22      0.0152648000
_diffrn_orient_matrix_UB_23      0.0016387000
_diffrn_orient_matrix_UB_31      -0.0184521000
_diffrn_orient_matrix_UB_32      0.0118835000
_diffrn_orient_matrix_UB_33      0.0772523000
_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                3625
_reflns_number_total             4728
_reflns_odcompleteness_completeness 99.71
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.884
_refine_diff_density_min         -0.736
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4728
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.064
_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)+(0.0356P)²+2.3098P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1001
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 O1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C21(H21), C5(H5), C3(H3), C13(H13), C12(H12), C4(H4),
 C8(H8), C18(H18), C14(H14), C17(H17), C16(H16)
2.c Idealised Me refined as rotating group:
 C69(H69A,H69B,H69C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
Br1 Br 0.73788(5) 0.21209(2) 0.01274(7) 0.06777(17) Uani 1 1 d . . . . .
Cu1 Cu 0.20514(4) 0.10007(2) 0.88407(6) 0.03126(12) Uani 1 1 d . . . . .
Cl1 Cl 0.01107(9) 0.08149(3) 0.93963(15) 0.0461(2) Uani 1 1 d . . . . .
Cl2 Cl 0.31459(9) 0.12093(3) 1.21315(13) 0.0457(2) Uani 1 1 d . . . . .
O1 O 0.5398(2) 0.18895(9) 0.2524(4) 0.0448(6) Uani 1 1 d . . . . .
H1 H 0.484008 0.168655 0.245540 0.067 Uiso 1 1 d R U . . .
N3 N 0.1752(3) 0.16993(9) 0.8229(4) 0.0326(6) Uani 1 1 d . . . . .
N1 N 0.2785(3) 0.03440(9) 0.8657(4) 0.0300(6) Uani 1 1 d . . . . .
N2 N 0.3552(3) 0.11444(9) 0.7681(4) 0.0285(6) Uani 1 1 d . . . . .
C19 C 0.2773(3) 0.19197(11) 0.7697(4) 0.0305(7) Uani 1 1 d . . . . .
C11 C 0.4517(3) -0.00913(12) 0.7715(5) 0.0353(8) Uani 1 1 d . . . . .
H11 H 0.527415 -0.009652 0.720042 0.042 Uiso 1 1 calc R U . . .
C9 C 0.4316(3) 0.07938(11) 0.7323(4) 0.0293(7) Uani 1 1 d . . . . .
C1 C 0.6533(3) 0.16947(11) 0.3243(5) 0.0323(7) Uani 1 1 d . . . . .
C6 C 0.6696(3) 0.14346(12) 0.4877(5) 0.0328(7) Uani 1 1 d . . . . .
C15 C 0.0752(3) 0.19562(13) 0.8575(5) 0.0392(8) Uani 1 1 d . . . . .
H15 H 0.004002 0.180275 0.891108 0.047 Uiso 1 1 calc R U . . .
C21 C 0.4808(3) 0.17045(12) 0.6348(4) 0.0323(7) Uani 1 1 d . . . . .
H21 H 0.496358 0.201577 0.604413 0.039 Uiso 1 1 calc R U . . .
C10 C 0.3880(3) 0.03293(11) 0.7897(4) 0.0293(7) Uani 1 1 d . . . . .
C20 C 0.3780(3) 0.15916(11) 0.7238(4) 0.0295(7) Uani 1 1 d . . . . .
C5 C 0.7886(3) 0.12419(14) 0.5494(5) 0.0430(9) Uani 1 1 d . . . . .
H5 H 0.799894 0.106930 0.658008 0.052 Uiso 1 1 calc R U . . .
C3 C 0.8752(3) 0.15625(13) 0.2929(5) 0.0424(9) Uani 1 1 d . . . . .
H3 H 0.943665 0.160538 0.227092 0.051 Uiso 1 1 calc R U . . .
C13 C 0.2892(4) -0.04857(12) 0.9065(5) 0.0408(9) Uani 1 1 d . . . . .
H13 H 0.253989 -0.076020 0.947541 0.049 Uiso 1 1 calc R U . . .
C12 C 0.4009(4) -0.05025(12) 0.8311(5) 0.0398(8) Uani 1 1 d . . . . .
H12 H 0.442101 -0.078910 0.820156 0.048 Uiso 1 1 calc R U . . .
C7 C 0.5611(3) 0.13423(12) 0.5913(4) 0.0319(7) Uani 1 1 d . . . . .
C4 C 0.8903(4) 0.13027(14) 0.4520(6) 0.0467(10) Uani 1 1 d . . . . .
H4 H 0.969095 0.116755 0.494093 0.056 Uiso 1 1 calc R U . . .
C8 C 0.5369(3) 0.08819(12) 0.6440(5) 0.0327(7) Uani 1 1 d . . . . .
H8 H 0.590971 0.063695 0.620139 0.039 Uiso 1 1 calc R U . . .
C18 C 0.2834(4) 0.24047(12) 0.7598(5) 0.0383(8) Uani 1 1 d . . . . .
H18 H 0.355794 0.255257 0.727493 0.046 Uiso 1 1 calc R U . . .
C14 C 0.2297(3) -0.00564(12) 0.9207(5) 0.0361(8) Uani 1 1 d . . . . .
H14 H 0.153144 -0.004645 0.970135 0.043 Uiso 1 1 calc R U . . .
C17 C 0.1806(4) 0.26664(13) 0.7984(5) 0.0454(9) Uani 1 1 d . . . . .
H17 H 0.182840 0.299413 0.793283 0.055 Uiso 1 1 calc R U . . .
C16 C 0.0740(4) 0.24385(13) 0.8450(5) 0.0451(9) Uani 1 1 d . . . . .
H16 H 0.002593 0.260949 0.867451 0.054 Uiso 1 1 calc R U . . .
C2 C 0.7584(3) 0.17589(12) 0.2316(5) 0.0351(8) Uani 1 1 d . . . . .
C69 C 0.1387(5) 0.0162(2) 0.4072(7) 0.0754(15) Uani 1 1 d . . . . .
H69A H 0.082585 0.015054 0.293070 0.113 Uiso 1 1 calc R U . . .
H69B H 0.118247 0.043147 0.476671 0.113 Uiso 1 1 calc R U . . .
H69C H 0.128501 -0.012039 0.476158 0.113 Uiso 1 1 calc R U . . .
O2 O 0.2646(4) 0.01953(14) 0.3720(6) 0.0881(11) Uani 1 1 d . . . . .
H2 H 0.275723 0.045207 0.325212 0.132 Uiso 1 1 calc R U . . .


_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
Br1 C2 1.895(4) . ?
Cu1 Cl1 2.2068(9) . ?
Cu1 Cl2 2.6030(10) . ?
Cu1 N3 2.045(3) . ?
Cu1 N1 2.027(3) . ?
Cu1 N2 1.941(3) . ?
O1 H1 0.8199 . ?
O1 C1 1.361(4) . ?
N3 C19 1.349(4) . ?
N3 C15 1.335(4) . ?
N1 C10 1.351(4) . ?
N1 C14 1.331(4) . ?
N2 C9 1.329(4) . ?
N2 C20 1.338(4) . ?
C19 C20 1.485(4) . ?
C19 C18 1.378(5) . ?
C11 H11 0.9300 . ?
C11 C10 1.384(5) . ?
C11 C12 1.378(5) . ?
C9 C10 1.475(4) . ?
C9 C8 1.384(4) . ?
C1 C6 1.399(5) . ?
C1 C2 1.390(5) . ?
C6 C5 1.389(5) . ?
C6 C7 1.482(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.370(5) . ?
C21 H21 0.9300 . ?
C21 C20 1.379(4) . ?
C21 C7 1.396(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.379(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(5) . ?
C3 C2 1.373(5) . ?
C13 H13 0.9300 . ?
C13 C12 1.369(5) . ?
C13 C14 1.380(5) . ?
C12 H12 0.9300 . ?
C7 C8 1.394(5) . ?
C4 H4 0.9300 . ?
C8 H8 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.376(5) . ?
C14 H14 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.380(5) . ?
C16 H16 0.9300 . ?
C69 H69A 0.9600 . ?
C69 H69B 0.9600 . ?
C69 H69C 0.9600 . ?
C69 O2 1.391(6) . ?
O2 H2 0.8200 . ?

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
Cl1 Cu1 Cl2 100.94(4) . . ?
N3 Cu1 Cl1 98.73(8) . . ?
N3 Cu1 Cl2 91.16(8) . . ?
N1 Cu1 Cl1 99.55(8) . . ?
N1 Cu1 Cl2 98.30(8) . . ?
N1 Cu1 N3 157.39(11) . . ?
N2 Cu1 Cl1 164.76(9) . . ?
N2 Cu1 Cl2 94.21(8) . . ?
N2 Cu1 N3 79.14(11) . . ?
N2 Cu1 N1 79.72(11) . . ?
C1 O1 H1 109.1 . . ?
C19 N3 Cu1 114.0(2) . . ?
C15 N3 Cu1 126.1(2) . . ?
C15 N3 C19 119.1(3) . . ?
C10 N1 Cu1 114.3(2) . . ?
C14 N1 Cu1 126.5(2) . . ?
C14 N1 C10 119.2(3) . . ?
C9 N2 Cu1 118.9(2) . . ?
C9 N2 C20 121.8(3) . . ?
C20 N2 Cu1 119.3(2) . . ?
N3 C19 C20 113.6(3) . . ?
N3 C19 C18 121.5(3) . . ?
C18 C19 C20 124.9(3) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C12 C11 C10 118.9(3) . . ?
N2 C9 C10 112.9(3) . . ?
N2 C9 C8 120.4(3) . . ?
C8 C9 C10 126.6(3) . . ?
O1 C1 C6 123.2(3) . . ?
O1 C1 C2 118.4(3) . . ?
C2 C1 C6 118.4(3) . . ?
C1 C6 C7 121.3(3) . . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 C7 119.5(3) . . ?
N3 C15 H15 119.0 . . ?
N3 C15 C16 122.1(3) . . ?
C16 C15 H15 119.0 . . ?
C20 C21 H21 120.7 . . ?
C20 C21 C7 118.7(3) . . ?
C7 C21 H21 120.7 . . ?
N1 C10 C11 121.4(3) . . ?
N1 C10 C9 114.1(3) . . ?
C11 C10 C9 124.5(3) . . ?
N2 C20 C19 112.4(3) . . ?
N2 C20 C21 120.9(3) . . ?
C21 C20 C19 126.6(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.0(4) . . ?
C4 C5 H5 119.5 . . ?
C4 C3 H3 120.2 . . ?
C4 C3 C2 119.5(3) . . ?
C2 C3 H3 120.2 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.2(3) . . ?
C14 C13 H13 120.4 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.5(3) . . ?
C13 C12 H12 120.3 . . ?
C21 C7 C6 121.6(3) . . ?
C8 C7 C6 119.4(3) . . ?
C8 C7 C21 119.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.0(4) . . ?
C3 C4 H4 120.0 . . ?
C9 C8 C7 119.2(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C19 C18 H18 120.6 . . ?
C17 C18 C19 118.9(3) . . ?
C17 C18 H18 120.6 . . ?
N1 C14 C13 121.9(3) . . ?
N1 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C18 C17 H17 120.3 . . ?
C18 C17 C16 119.4(3) . . ?
C16 C17 H17 120.3 . . ?
C15 C16 C17 118.9(4) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 H16 120.5 . . ?
C1 C2 Br1 118.6(3) . . ?
C3 C2 Br1 119.5(3) . . ?
C3 C2 C1 121.8(3) . . ?
H69A C69 H69B 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 109.5 . . ?
O2 C69 H69A 109.5 . . ?
O2 C69 H69B 109.5 . . ?
O2 C69 H69C 109.5 . . ?
C69 O2 H2 109.5 . . ?

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 N3 C19 C20 13.8(4) . . . . ?
Cu1 N3 C19 C18 -166.5(3) . . . . ?
Cu1 N3 C15 C16 167.1(3) . . . . ?
Cu1 N1 C10 C11 178.4(2) . . . . ?
Cu1 N1 C10 C9 -0.9(4) . . . . ?
Cu1 N1 C14 C13 -178.2(3) . . . . ?
Cu1 N2 C9 C10 -0.1(4) . . . . ?
Cu1 N2 C9 C8 177.8(2) . . . . ?
Cu1 N2 C20 C19 -1.4(4) . . . . ?
Cu1 N2 C20 C21 -177.5(2) . . . . ?
O1 C1 C6 C5 178.9(3) . . . . ?
O1 C1 C6 C7 1.8(5) . . . . ?
O1 C1 C2 Br1 0.9(4) . . . . ?
O1 C1 C2 C3 -178.2(3) . . . . ?
N3 C19 C20 N2 -8.4(4) . . . . ?
N3 C19 C20 C21 167.4(3) . . . . ?
N3 C19 C18 C17 -2.6(5) . . . . ?
N3 C15 C16 C17 -1.2(6) . . . . ?
N2 C9 C10 N1 0.7(4) . . . . ?
N2 C9 C10 C11 -178.6(3) . . . . ?
N2 C9 C8 C7 -0.7(5) . . . . ?
C19 N3 C15 C16 -1.7(5) . . . . ?
C19 C18 C17 C16 -0.4(6) . . . . ?
C9 N2 C20 C19 177.6(3) . . . . ?
C9 N2 C20 C21 1.5(5) . . . . ?
C1 C6 C5 C4 -0.1(6) . . . . ?
C1 C6 C7 C21 -49.7(5) . . . . ?
C1 C6 C7 C8 129.2(4) . . . . ?
C6 C1 C2 Br1 -178.8(2) . . . . ?
C6 C1 C2 C3 2.1(5) . . . . ?
C6 C5 C4 C3 1.0(6) . . . . ?
C6 C7 C8 C9 -176.7(3) . . . . ?
C15 N3 C19 C20 -176.1(3) . . . . ?
C15 N3 C19 C18 3.6(5) . . . . ?
C21 C7 C8 C9 2.2(5) . . . . ?
C10 N1 C14 C13 1.6(5) . . . . ?
C10 C11 C12 C13 0.0(5) . . . . ?
C10 C9 C8 C7 176.9(3) . . . . ?
C20 N2 C9 C10 -179.1(3) . . . . ?
C20 N2 C9 C8 -1.2(5) . . . . ?
C20 C19 C18 C17 177.1(3) . . . . ?
C20 C21 C7 C6 176.9(3) . . . . ?
C20 C21 C7 C8 -1.9(5) . . . . ?
C5 C6 C7 C21 133.2(4) . . . . ?
C5 C6 C7 C8 -47.9(5) . . . . ?
C12 C11 C10 N1 0.6(5) . . . . ?
C12 C11 C10 C9 179.9(3) . . . . ?
C12 C13 C14 N1 -1.0(6) . . . . ?
C7 C6 C5 C4 177.1(4) . . . . ?
C7 C21 C20 N2 0.1(5) . . . . ?
C7 C21 C20 C19 -175.4(3) . . . . ?
C4 C3 C2 Br1 179.6(3) . . . . ?
C4 C3 C2 C1 -1.3(5) . . . . ?
C8 C9 C10 N1 -177.1(3) . . . . ?
C8 C9 C10 C11 3.6(6) . . . . ?
C18 C19 C20 N2 171.9(3) . . . . ?
C18 C19 C20 C21 -12.3(6) . . . . ?
C18 C17 C16 C15 2.2(6) . . . . ?
C14 N1 C10 C11 -1.4(5) . . . . ?
C14 N1 C10 C9 179.3(3) . . . . ?
C14 C13 C12 C11 0.2(6) . . . . ?
C2 C1 C6 C5 -1.3(5) . . . . ?
C2 C1 C6 C7 -178.5(3) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?

_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 1.686
_oxdiff_exptl_absorpt_empirical_full_min 0.680
####################################################################### 
# 
# 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_aaaa
_database_code_depnum_ccdc_archive 'CCDC 2102156'
loop_
_audit_author_name
_audit_author_address
'Yunqiong Gu'
;Guangxi Normal University
China
;
_audit_update_record             
;
2021-11-14 deposited with the CCDC.	2021-12-08 downloaded from the CCDC.
;
_audit_creation_date             2021-11-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H24 Br Cu N3 O3 S, O, H2 O'
_chemical_formula_sum            'C24 H26 Br Cu N3 O5 S'
_chemical_formula_weight         611.99
_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'
S S 0.1246 0.1234 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.639(6)
_cell_length_b                   7.799(3)
_cell_length_c                   20.545(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.491(4)
_cell_angle_gamma                90
_cell_volume                     2967.1(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7376
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.23
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.694
_shelx_estimated_absorpt_T_min   0.633
_exptl_absorpt_coefficient_mu    2.187
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark blue'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1244
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22027
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         1.995
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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                3886
_reflns_number_total             5192
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.859
_refine_diff_density_min         -0.968
_refine_diff_density_rms         0.149
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         5192
_refine_ls_number_restraints     103
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0780
_refine_ls_restrained_S_all      1.061
_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)+(0.1186P)²+14.3160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2071
_refine_ls_wR_factor_ref         0.2237
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C22-C23 \\sim C22A-C23A
 with sigma of 0.02
 S1A-C23A \\sim S1A-C22A
 with sigma of 0.02
 S1-C23 \\sim S1-C22
 with sigma of 0.02
 S1-O1 \\sim S1A-O1
 with sigma of 0.02
 S1-C22 \\sim S1-C23
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
C22 \\sim C23: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
S1 \\sim O1 \\sim C23 \\sim C22 \\sim S1A \\sim C23A \\sim C22A: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
S1 \\sim O1 \\sim C23 \\sim C22: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
Uanis(C22) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.04
3. Rigid body (RIGU) restrains
 C22A, C23A, O1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 S1, C22, C23, O1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 O1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C23, S1, C22, O1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Others
 Sof(S1A)=Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=Sof(C22A)=Sof(H22D)=
 Sof(H22E)=Sof(H22F)=1-FVAR(1)
 Sof(S1)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(C22)=Sof(H22A)=Sof(H22B)=
 Sof(H22C)=FVAR(1)
5.a Riding coordinates:
 O5(H5A,H5B), C22A(H22D,H22E,H22F)
5.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C4(H4), C7(H7), C15(H15), C13(H13), C19(H19), C1(H1),
 C3(H3A), C18(H18), C20(H20), C2(H2A), C21(H21)
5.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C22(H22A,H22B,H22C), C23A(H23D,H23E,
 H23F)
5.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_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 0.27342(4) 0.54417(13) 0.37051(4) 0.0396(3) Uani 1 1 d . . . A 1
Br1 Br -0.23518(4) 0.36043(12) 0.28579(4) 0.0514(3) Uani 1 1 d . . . A 1
S1 S 0.40555(14) 0.7789(4) 0.39378(15) 0.0636(9) Uani 0.889(6) 1 d D U P A 1
N2 N 0.1765(3) 0.5386(7) 0.3283(2) 0.0268(12) Uani 1 1 d . . . A 1
O3 O -0.0029(3) 0.6630(8) 0.1385(2) 0.0414(13) Uani 1 1 d . . . A 1
H3 H -0.021058 0.720285 0.107440 0.062 Uiso 1 1 calc R U . A 1
C8 C 0.0376(3) 0.5373(9) 0.2667(3) 0.0257(14) Uani 1 1 d . . . A 1
C16 C 0.1633(3) 0.4741(9) 0.2673(3) 0.0293(15) Uani 1 1 d . . . A 1
C9 C -0.0384(3) 0.5319(9) 0.2346(3) 0.0267(14) Uani 1 1 d . . . A 1
C5 C 0.1515(4) 0.6863(9) 0.4231(3) 0.0313(15) Uani 1 1 d . . . A 1
C25 C 0.1239(4) 0.6084(9) 0.3593(3) 0.0283(14) Uani 1 1 d . . . A 1
O1 O 0.3736(3) 0.6055(9) 0.3974(3) 0.0593(15) Uani 1 1 d D U . . .
N1 N 0.2240(3) 0.6759(9) 0.4368(3) 0.0391(14) Uani 1 1 d . . . A 1
N3 N 0.2904(3) 0.4210(9) 0.2869(3) 0.0404(15) Uani 1 1 d . . . A 1
C10 C -0.0919(3) 0.4706(9) 0.2692(3) 0.0298(15) Uani 1 1 d . . . A 1
H10 H -0.080686 0.432872 0.312121 0.036 Uiso 1 1 calc R U . A 1
C14 C -0.0566(4) 0.5968(9) 0.1719(3) 0.0293(15) Uani 1 1 d . . . A 1
C11 C -0.1631(4) 0.4654(11) 0.2397(4) 0.0399(18) Uani 1 1 d . . . A 1
C17 C 0.2306(4) 0.4029(10) 0.2447(3) 0.0333(16) Uani 1 1 d . . . A 1
C12 C -0.1802(3) 0.5258(10) 0.1783(3) 0.0346(16) Uani 1 1 d . . . A 1
H12 H -0.227822 0.520978 0.159159 0.042 Uiso 1 1 calc R U . A 1
C4 C 0.1092(4) 0.7618(10) 0.4658(3) 0.0352(16) Uani 1 1 d . . . A 1
H4 H 0.059428 0.769978 0.455262 0.042 Uiso 1 1 calc R U . A 1
C7 C 0.0525(4) 0.6071(9) 0.3296(3) 0.0313(15) Uani 1 1 d . . . A 1
H7 H 0.015556 0.651828 0.351313 0.038 Uiso 1 1 calc R U . A 1
C15 C 0.0945(3) 0.4738(9) 0.2346(3) 0.0278(14) Uani 1 1 d . . . A 1
H15 H 0.086050 0.432131 0.191994 0.033 Uiso 1 1 calc R U . A 1
C13 C -0.1281(4) 0.5942(10) 0.1440(3) 0.0350(16) Uani 1 1 d . . . A 1
H13 H -0.140559 0.638524 0.102201 0.042 Uiso 1 1 calc R U . A 1
O2 O 0.2775(3) 0.3045(10) 0.4353(3) 0.0635(18) Uani 1 1 d . . . A 1
H2 H 0.244302 0.239160 0.441030 0.095 Uiso 1 1 calc R U . A 1
C19 C 0.2975(5) 0.2580(12) 0.1690(5) 0.054(2) Uani 1 1 d . . . A 1
H19 H 0.299941 0.204987 0.128748 0.065 Uiso 1 1 calc R U . A 1
C1 C 0.2548(4) 0.7432(12) 0.4933(4) 0.048(2) Uani 1 1 d . . . A 1
H1 H 0.304736 0.737484 0.502396 0.058 Uiso 1 1 calc R U . A 1
C3 C 0.1419(5) 0.8252(11) 0.5246(4) 0.048(2) Uani 1 1 d . . . A 1
H3A H 0.113557 0.871092 0.554795 0.058 Uiso 1 1 calc R U . A 1
C18 C 0.2329(4) 0.3237(10) 0.1851(4) 0.0409(18) Uani 1 1 d . . . A 1
H18 H 0.191187 0.314404 0.155842 0.049 Uiso 1 1 calc R U . A 1
C20 C 0.3572(4) 0.2723(13) 0.2128(5) 0.057(2) Uani 1 1 d . . . A 1
H20 H 0.400937 0.225505 0.203826 0.068 Uiso 1 1 calc R U . A 1
C2 C 0.2154(5) 0.8216(12) 0.5392(4) 0.049(2) Uani 1 1 d . . . A 1
H2A H 0.238092 0.868880 0.577660 0.059 Uiso 1 1 calc R U . A 1
C21 C 0.3523(4) 0.3565(12) 0.2704(5) 0.054(2) Uani 1 1 d . . . A 1
H21 H 0.393935 0.369527 0.299564 0.064 Uiso 1 1 calc R U . A 1
C23 C 0.4944(5) 0.751(2) 0.4364(6) 0.072(4) Uani 0.889(6) 1 d D U P A 1
H23A H 0.492605 0.667755 0.470727 0.107 Uiso 0.889(6) 1 calc R U P A 1
H23B H 0.511595 0.857997 0.454934 0.107 Uiso 0.889(6) 1 calc R U P A 1
H23C H 0.526560 0.710868 0.406255 0.107 Uiso 0.889(6) 1 calc R U P A 1
C24 C 0.3411(6) 0.2459(18) 0.4704(6) 0.089(4) Uani 1 1 d . . . A 1
H24A H 0.381496 0.278560 0.448098 0.134 Uiso 1 1 calc R U . A 1
H24B H 0.339425 0.123206 0.473897 0.134 Uiso 1 1 calc R U . A 1
H24C H 0.346047 0.295458 0.513457 0.134 Uiso 1 1 calc R U . A 1
C22 C 0.4328(7) 0.791(2) 0.3137(6) 0.092(3) Uani 0.889(6) 1 d D U P A 1
H22A H 0.456232 0.686340 0.303824 0.137 Uiso 0.889(6) 1 calc R U P A 1
H22B H 0.465659 0.885313 0.311565 0.137 Uiso 0.889(6) 1 calc R U P A 1
H22C H 0.391116 0.808769 0.282393 0.137 Uiso 0.889(6) 1 calc R U P A 1
O4 O 0.2726(6) 0.966(3) 0.3728(6) 0.191(7) Uani 1 1 d . . . B 2
O5 O 0.2343(5) 0.6447(18) 0.2173(6) 0.135(4) Uani 1 1 d . . . C 2
H5A H 0.271166 0.703060 0.210150 0.202 Uiso 1 1 d R U . C 2
H5B H 0.198746 0.710620 0.206180 0.202 Uiso 1 1 d R U . C 2
S1A S 0.4300(10) 0.696(4) 0.3623(11) 0.064(3) Uani 0.111(6) 1 d D U P A 2
C23A C 0.413(5) 0.914(11) 0.328(4) 0.071(7) Uani 0.111(6) 1 d D U P A 2
H23D H 0.380537 0.906887 0.288356 0.106 Uiso 0.111(6) 1 calc R U P A 2
H23E H 0.457971 0.963613 0.318366 0.106 Uiso 0.111(6) 1 calc R U P A 2
H23F H 0.392323 0.984454 0.359154 0.106 Uiso 0.111(6) 1 calc R U P A 2
C22A C 0.474(5) 0.783(18) 0.441(3) 0.065(7) Uani 0.111(6) 1 d D U P A 2
H22D H 0.458454 0.899233 0.445481 0.097 Uiso 0.111(6) 1 d R U P A 2
H22E H 0.525714 0.781673 0.439941 0.097 Uiso 0.111(6) 1 d R U P A 2
H22F H 0.462084 0.716103 0.477161 0.097 Uiso 0.111(6) 1 d R U P A 2


_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 N2 1.915(5) . ?
Cu1 O1 1.946(5) . ?
Cu1 N1 2.010(6) . ?
Cu1 N3 2.024(6) . ?
Cu1 O2 2.291(7) . ?
Br1 C11 1.914(8) . ?
S1 O1 1.483(7) . ?
S1 C23 1.798(9) . ?
S1 C22 1.779(12) . ?
N2 C16 1.346(8) . ?
N2 C25 1.342(8) . ?
O3 H3 0.8200 . ?
O3 C14 1.377(8) . ?
C8 C9 1.494(8) . ?
C8 C7 1.402(9) . ?
C8 C15 1.401(9) . ?
C16 C17 1.492(10) . ?
C16 C15 1.379(9) . ?
C9 C10 1.375(9) . ?
C9 C14 1.389(9) . ?
C5 C25 1.484(9) . ?
C5 N1 1.351(9) . ?
C5 C4 1.377(10) . ?
C25 C7 1.400(9) . ?
O1 S1A 1.515(17) . ?
N1 C1 1.343(10) . ?
N3 C17 1.340(9) . ?
N3 C21 1.337(10) . ?
C10 H10 0.9300 . ?
C10 C11 1.396(9) . ?
C14 C13 1.390(9) . ?
C11 C12 1.350(11) . ?
C17 C18 1.377(11) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(10) . ?
C4 H4 0.9300 . ?
C4 C3 1.382(11) . ?
C7 H7 0.9300 . ?
C15 H15 0.9300 . ?
C13 H13 0.9300 . ?
O2 H2 0.8200 . ?
O2 C24 1.393(11) . ?
C19 H19 0.9300 . ?
C19 C18 1.384(11) . ?
C19 C20 1.355(13) . ?
C1 H1 0.9300 . ?
C1 C2 1.398(12) . ?
C3 H3A 0.9300 . ?
C3 C2 1.370(12) . ?
C18 H18 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.366(13) . ?
C2 H2A 0.9300 . ?
C21 H21 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
O5 H5A 0.8500 . ?
O5 H5B 0.8500 . ?
S1A C23A 1.86(7) . ?
S1A C22A 1.86(7) . ?
C23A H23D 0.9600 . ?
C23A H23E 0.9600 . ?
C23A H23F 0.9600 . ?
C22A H22D 0.9600 . ?
C22A H22E 0.9600 . ?
C22A H22F 0.9601 . ?

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
N2 Cu1 O1 163.8(3) . . ?
N2 Cu1 N1 80.6(2) . . ?
N2 Cu1 N3 80.5(2) . . ?
N2 Cu1 O2 102.3(2) . . ?
O1 Cu1 N1 100.4(3) . . ?
O1 Cu1 N3 96.9(2) . . ?
O1 Cu1 O2 93.9(3) . . ?
N1 Cu1 N3 160.9(2) . . ?
N1 Cu1 O2 90.6(3) . . ?
N3 Cu1 O2 96.2(3) . . ?
O1 S1 C23 102.5(6) . . ?
O1 S1 C22 104.7(6) . . ?
C22 S1 C23 96.5(6) . . ?
C16 N2 Cu1 119.5(4) . . ?
C25 N2 Cu1 118.5(4) . . ?
C25 N2 C16 121.8(5) . . ?
C14 O3 H3 109.5 . . ?
C7 C8 C9 119.8(6) . . ?
C15 C8 C9 120.9(6) . . ?
C15 C8 C7 119.4(6) . . ?
N2 C16 C17 111.0(5) . . ?
N2 C16 C15 121.0(6) . . ?
C15 C16 C17 128.0(6) . . ?
C10 C9 C8 119.2(5) . . ?
C10 C9 C14 119.4(6) . . ?
C14 C9 C8 121.3(6) . . ?
N1 C5 C25 113.4(6) . . ?
N1 C5 C4 121.7(6) . . ?
C4 C5 C25 124.9(6) . . ?
N2 C25 C5 112.8(6) . . ?
N2 C25 C7 119.9(6) . . ?
C7 C25 C5 127.2(6) . . ?
S1 O1 Cu1 126.0(4) . . ?
C5 N1 Cu1 114.5(5) . . ?
C1 N1 Cu1 127.0(5) . . ?
C1 N1 C5 118.3(7) . . ?
C17 N3 Cu1 113.6(5) . . ?
C21 N3 Cu1 128.0(6) . . ?
C21 N3 C17 118.4(7) . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(6) . . ?
C11 C10 H10 120.2 . . ?
O3 C14 C9 118.9(6) . . ?
O3 C14 C13 121.1(6) . . ?
C9 C14 C13 120.0(6) . . ?
C10 C11 Br1 118.9(6) . . ?
C12 C11 Br1 120.4(5) . . ?
C12 C11 C10 120.6(7) . . ?
N3 C17 C16 115.3(6) . . ?
N3 C17 C18 121.0(7) . . ?
C18 C17 C16 123.7(6) . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.6(6) . . ?
C13 C12 H12 119.7 . . ?
C5 C4 H4 120.6 . . ?
C5 C4 C3 118.8(7) . . ?
C3 C4 H4 120.6 . . ?
C8 C7 H7 120.5 . . ?
C25 C7 C8 118.9(6) . . ?
C25 C7 H7 120.5 . . ?
C8 C15 H15 120.6 . . ?
C16 C15 C8 118.8(6) . . ?
C16 C15 H15 120.6 . . ?
C14 C13 H13 120.2 . . ?
C12 C13 C14 119.6(6) . . ?
C12 C13 H13 120.2 . . ?
Cu1 O2 H2 127.9 . . ?
C24 O2 Cu1 122.6(7) . . ?
C24 O2 H2 109.5 . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C20 C19 C18 118.8(8) . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C2 123.3(7) . . ?
C2 C1 H1 118.4 . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 C4 121.0(7) . . ?
C2 C3 H3A 119.5 . . ?
C17 C18 C19 119.7(8) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C19 C20 H20 120.5 . . ?
C19 C20 C21 119.0(8) . . ?
C21 C20 H20 120.5 . . ?
C1 C2 H2A 121.6 . . ?
C3 C2 C1 116.8(7) . . ?
C3 C2 H2A 121.6 . . ?
N3 C21 C20 123.0(8) . . ?
N3 C21 H21 118.5 . . ?
C20 C21 H21 118.5 . . ?
S1 C23 H23A 109.5 . . ?
S1 C23 H23B 109.5 . . ?
S1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
S1 C22 H22A 109.5 . . ?
S1 C22 H22B 109.5 . . ?
S1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H5A O5 H5B 104.5 . . ?
O1 S1A C23A 121(3) . . ?
O1 S1A C22A 91(4) . . ?
C23A S1A C22A 92(5) . . ?
S1A C23A H23D 109.5 . . ?
S1A C23A H23E 109.5 . . ?
S1A C23A H23F 109.5 . . ?
H23D C23A H23E 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
S1A C22A H22D 108.7 . . ?
S1A C22A H22E 109.0 . . ?
S1A C22A H22F 110.7 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?

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 N2 C16 C17 4.4(8) . . . . ?
Cu1 N2 C16 C15 -177.7(5) . . . . ?
Cu1 N2 C25 C5 1.9(8) . . . . ?
Cu1 N2 C25 C7 179.7(5) . . . . ?
Cu1 N1 C1 C2 -174.8(7) . . . . ?
Cu1 N3 C17 C16 -0.7(8) . . . . ?
Cu1 N3 C17 C18 179.2(6) . . . . ?
Cu1 N3 C21 C20 178.7(7) . . . . ?
Br1 C11 C12 C13 -177.1(6) . . . . ?
N2 C16 C17 N3 -2.2(9) . . . . ?
N2 C16 C17 C18 177.9(7) . . . . ?
N2 C16 C15 C8 -1.9(10) . . . . ?
N2 C25 C7 C8 -2.0(10) . . . . ?
O3 C14 C13 C12 179.4(7) . . . . ?
C8 C9 C10 C11 179.9(6) . . . . ?
C8 C9 C14 O3 1.7(10) . . . . ?
C8 C9 C14 C13 -178.3(6) . . . . ?
C16 N2 C25 C5 -174.4(6) . . . . ?
C16 N2 C25 C7 3.4(10) . . . . ?
C16 C17 C18 C19 -178.5(8) . . . . ?
C9 C8 C7 C25 178.9(6) . . . . ?
C9 C8 C15 C16 -177.0(6) . . . . ?
C9 C10 C11 Br1 174.3(5) . . . . ?
C9 C10 C11 C12 -2.5(11) . . . . ?
C9 C14 C13 C12 -0.6(11) . . . . ?
C5 C25 C7 C8 175.5(6) . . . . ?
C5 N1 C1 C2 0.9(13) . . . . ?
C5 C4 C3 C2 3.3(13) . . . . ?
C25 N2 C16 C17 -179.3(6) . . . . ?
C25 N2 C16 C15 -1.4(10) . . . . ?
C25 C5 N1 Cu1 -4.1(8) . . . . ?
C25 C5 N1 C1 179.7(7) . . . . ?
C25 C5 C4 C3 178.2(7) . . . . ?
N1 C5 C25 N2 1.6(9) . . . . ?
N1 C5 C25 C7 -176.1(7) . . . . ?
N1 C5 C4 C3 -1.3(11) . . . . ?
N1 C1 C2 C3 1.0(14) . . . . ?
N3 C17 C18 C19 1.5(12) . . . . ?
C10 C9 C14 O3 177.9(6) . . . . ?
C10 C9 C14 C13 -2.1(10) . . . . ?
C10 C11 C12 C13 -0.3(12) . . . . ?
C14 C9 C10 C11 3.7(10) . . . . ?
C11 C12 C13 C14 1.8(11) . . . . ?
C17 C16 C15 C8 175.6(7) . . . . ?
C17 N3 C21 C20 -0.4(13) . . . . ?
C4 C5 C25 N2 -177.9(7) . . . . ?
C4 C5 C25 C7 4.4(12) . . . . ?
C4 C5 N1 Cu1 175.4(6) . . . . ?
C4 C5 N1 C1 -0.7(11) . . . . ?
C4 C3 C2 C1 -3.1(13) . . . . ?
C7 C8 C9 C10 -48.1(9) . . . . ?
C7 C8 C9 C14 128.1(7) . . . . ?
C7 C8 C15 C16 3.2(10) . . . . ?
C15 C8 C9 C10 132.1(7) . . . . ?
C15 C8 C9 C14 -51.7(9) . . . . ?
C15 C8 C7 C25 -1.2(10) . . . . ?
C15 C16 C17 N3 -179.9(7) . . . . ?
C15 C16 C17 C18 0.1(12) . . . . ?
C19 C20 C21 N3 2.4(15) . . . . ?
C18 C19 C20 C21 -2.4(15) . . . . ?
C20 C19 C18 C17 0.5(14) . . . . ?
C21 N3 C17 C16 178.5(7) . . . . ?
C21 N3 C17 C18 -1.6(11) . . . . ?
C23 S1 O1 Cu1 172.2(6) . . . . ?
C22 S1 O1 Cu1 -87.6(7) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.590 0.000 171.6 89.7 '2 ClO4-'
2 0.000 -0.517 0.500 171.6 89.7 '2 ClO4-'
3 0.429 0.750 0.625 104.3 55.5 '1 ClO4-'
4 0.429 0.750 0.125 104.3 55.5 '1 ClO4-'
5 0.571 0.250 0.375 104.3 56.6 '1 ClO4-'
6 0.571 0.250 0.875 104.3 56.6 '1 ClO4-'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_20190422-czf-zyj-b4cuclo4aaa
_database_code_depnum_ccdc_archive 'CCDC 2102154'
loop_
_audit_author_name
_audit_author_address
'Yunqiong Gu'
;Guangxi Normal University
China
;
_audit_update_record             
;
2021-11-14 deposited with the CCDC.	2021-12-08 downloaded from the CCDC.
;
_audit_creation_date             2021-11-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 Br Cl Cu N3 O, Cl O4'
_chemical_formula_sum            'C21 H14 Br Cl2 Cu N3 O5'
_chemical_formula_weight         602.70
_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'
Cl Cl 0.1484 0.1585 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.7892(4)
_cell_length_b                   7.3307(3)
_cell_length_c                   25.4885(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.083(3)
_cell_angle_gamma                90
_cell_volume                     2386.17(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3588
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5670
_cell_measurement_theta_min      3.6440
_shelx_estimated_absorpt_T_max   0.726
_shelx_estimated_absorpt_T_min   0.388
_exptl_absorpt_coefficient_mu    2.851
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic bluish black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1196
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            17830
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.324
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  90.00   1.00    6.00    --   17.61  38.00   0.00   98
  2  ω     -8.00  90.00   1.00    6.00    --   17.61  38.00  90.00   98
  3  ω    -20.00  60.00   1.00    6.00    --   17.61 -99.00  90.00   80
  4  ω    -96.00 -34.00   1.00    6.00    --  -19.88 178.00-150.00   62
  5  ω    -96.00 -35.00   1.00    6.00    --  -19.88-178.00 -60.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0057921000
_diffrn_orient_matrix_UB_12      -0.0044861000
_diffrn_orient_matrix_UB_13      -0.0274990000
_diffrn_orient_matrix_UB_21      0.0549819000
_diffrn_orient_matrix_UB_22      -0.0087588000
_diffrn_orient_matrix_UB_23      0.0044848000
_diffrn_orient_matrix_UB_31      -0.0052711000
_diffrn_orient_matrix_UB_32      -0.0962344000
_diffrn_orient_matrix_UB_33      0.0008853000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\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                3368
_reflns_number_total             4869
_reflns_odcompleteness_completeness 99.64
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4869
_refine_ls_number_restraints     147
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.087
_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)+(0.0437P)²+3.1624P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1242
_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
 O2A-O4A
 2.5 with sigma of 0.02
 O5A-O4A
 2.5 with sigma of 0.02
 O5A-O3A
 2.5 with sigma of 0.02
 O5A-O2A
 2.5 with sigma of 0.02
 O3A-O5A
 2.5 with sigma of 0.02
 O4A-O5A
 2.5 with sigma of 0.02
 O3A-O2A
 2.5 with sigma of 0.02
 O2-O4 \\sim O5-O3
 with sigma of 0.002
 O4A-O5A \\sim O3A-O2A
 with sigma of 0.002
3. Uiso/Uaniso restraints and constraints
Cl2 \\sim O2 \\sim O4 \\sim O5 \\sim O3 \\sim O4A \\sim O5A \\sim O3A \\sim
O2A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(O5) \\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O3) \\sim
Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O2A) \\sim Ueq, Uanis(O4A) \\sim Ueq, Uanis(O5A) \\sim Ueq, Uanis(O3A)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 O2, O4, O5, O3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 O4A, O5A, O3A, O2A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 Sof(O4A)=Sof(O5A)=Sof(O3A)=Sof(O2A)=1-FVAR(1)
 Sof(O2)=Sof(O4)=Sof(O5)=Sof(O3)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C21(H21), C5(H5), C4(H4), C3(H3), C11(H11), C14(H14), C15(H15),
 C18(H18), C13(H13), C16(H16), C12(H12), C17(H17)
6.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.51113(4) 0.67209(8) 0.04698(2) 0.04366(18) Uani 1 1 d . . . . .
Br1 Br 1.09349(4) 0.50600(8) 0.29908(2) 0.0663(2) Uani 1 1 d . . . . .
N2 N 0.5952(3) 0.6804(5) 0.11185(13) 0.0383(8) Uani 1 1 d . . . . .
N3 N 0.6405(3) 0.7983(5) 0.02202(14) 0.0459(9) Uani 1 1 d . . . . .
C8 C 0.6168(3) 0.6006(6) 0.20131(16) 0.0382(10) Uani 1 1 d . . . . .
H8 H 0.588921 0.556688 0.231800 0.046 Uiso 1 1 calc R U . . .
C7 C 0.7215(3) 0.6554(6) 0.20138(16) 0.0393(10) Uani 1 1 d . . . . .
N1 N 0.4045(3) 0.5871(5) 0.09709(14) 0.0459(9) Uani 1 1 d . . . . .
C21 C 0.7593(3) 0.7264(6) 0.15572(16) 0.0402(10) Uani 1 1 d . . . . .
H21 H 0.828351 0.765739 0.155253 0.048 Uiso 1 1 calc R U . . .
C9 C 0.5557(3) 0.6128(6) 0.15516(16) 0.0371(10) Uani 1 1 d . . . . .
C1 C 0.8925(4) 0.5874(6) 0.25060(18) 0.0444(11) Uani 1 1 d . . . . .
C6 C 0.7880(3) 0.6432(6) 0.25108(16) 0.0383(10) Uani 1 1 d . . . . .
C10 C 0.4440(3) 0.5601(6) 0.14702(17) 0.0404(10) Uani 1 1 d . . . . .
C20 C 0.6939(3) 0.7384(6) 0.11077(17) 0.0378(10) Uani 1 1 d . . . . .
O1 O 0.9303(3) 0.5302(5) 0.20480(13) 0.0568(9) Uani 1 1 d . . . . .
H1 H 0.994431 0.535740 0.206797 0.085 Uiso 1 1 calc R U . . .
C2 C 0.9523(3) 0.5833(6) 0.2984(2) 0.0459(11) Uani 1 1 d . . . . .
C19 C 0.7189(3) 0.8133(6) 0.05923(17) 0.0426(11) Uani 1 1 d . . . . .
C5 C 0.7462(4) 0.6889(6) 0.29822(17) 0.0415(10) Uani 1 1 d . . . . .
H5 H 0.676244 0.723064 0.298524 0.050 Uiso 1 1 calc R U . . .
C4 C 0.8067(4) 0.6847(6) 0.34520(18) 0.0506(12) Uani 1 1 d . . . . .
H4 H 0.777818 0.716940 0.376590 0.061 Uiso 1 1 calc R U . . .
C3 C 0.9100(4) 0.6322(6) 0.34462(19) 0.0503(13) Uani 1 1 d . . . . .
H3 H 0.951363 0.629837 0.375770 0.060 Uiso 1 1 calc R U . . .
C11 C 0.3837(4) 0.4932(6) 0.18540(19) 0.0503(12) Uani 1 1 d . . . . .
H11 H 0.412747 0.474646 0.219219 0.060 Uiso 1 1 calc R U . . .
C14 C 0.3038(4) 0.5505(7) 0.0862(2) 0.0574(14) Uani 1 1 d . . . . .
H14 H 0.275858 0.570403 0.052251 0.069 Uiso 1 1 calc R U . . .
C15 C 0.6546(4) 0.8639(7) -0.02605(19) 0.0573(13) Uani 1 1 d . . . . .
H15 H 0.600391 0.854090 -0.051722 0.069 Uiso 1 1 calc R U . . .
C18 C 0.8114(4) 0.8969(7) 0.0486(2) 0.0581(14) Uani 1 1 d . . . . .
H18 H 0.864446 0.908748 0.074794 0.070 Uiso 1 1 calc R U . . .
C13 C 0.2393(4) 0.4841(8) 0.1233(2) 0.0704(16) Uani 1 1 d . . . . .
H13 H 0.169090 0.460175 0.114551 0.084 Uiso 1 1 calc R U . . .
C16 C 0.7459(5) 0.9447(8) -0.0386(2) 0.0663(15) Uani 1 1 d . . . . .
H16 H 0.753823 0.986928 -0.072517 0.080 Uiso 1 1 calc R U . . .
C12 C 0.2802(4) 0.4536(8) 0.1737(2) 0.0625(14) Uani 1 1 d . . . . .
H12 H 0.238415 0.407046 0.199266 0.075 Uiso 1 1 calc R U . . .
C17 C 0.8253(5) 0.9635(8) -0.0014(2) 0.0680(16) Uani 1 1 d . . . . .
H17 H 0.887627 1.019816 -0.009334 0.082 Uiso 1 1 calc R U . . .
Cl2 Cl 1.06736(11) 1.0055(3) 0.16077(6) 0.0883(6) Uani 1 1 d . U . . .
O2 O 0.9920(5) 0.9305(11) 0.1894(3) 0.088(2) Uani 0.717(7) 1 d D U P A 1
O4 O 1.1673(5) 0.9651(13) 0.1748(3) 0.110(3) Uani 0.717(7) 1 d D U P A 1
O5 O 1.0606(8) 1.2141(11) 0.1773(4) 0.152(3) Uani 0.717(7) 1 d D U P A 1
O3 O 1.0436(7) 1.0112(14) 0.1082(3) 0.129(3) Uani 0.717(7) 1 d D U P A 1
Cl1 Cl 0.41098(9) 0.67647(17) -0.02699(4) 0.0493(3) Uani 1 1 d . . . . .
O4A O 1.1133(15) 0.788(2) 0.1878(8) 0.128(5) Uani 0.283(7) 1 d D U P A 2
O5A O 1.1490(17) 1.103(3) 0.1635(8) 0.134(5) Uani 0.283(7) 1 d D U P A 2
O3A O 1.0578(12) 0.864(2) 0.1102(6) 0.082(4) Uani 0.283(7) 1 d D U P A 2
O2A O 0.9676(14) 1.005(3) 0.1817(9) 0.104(6) Uani 0.283(7) 1 d D U P A 2


_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 N2 1.924(3) . ?
Cu1 N3 2.028(4) . ?
Cu1 N1 2.017(4) . ?
Cu1 Cl1 2.2218(11) . ?
Br1 C2 1.892(5) . ?
N2 C9 1.334(5) . ?
N2 C20 1.333(5) . ?
N3 C19 1.347(5) . ?
N3 C15 1.337(6) . ?
C8 H8 0.9300 . ?
C8 C7 1.397(6) . ?
C8 C9 1.380(5) . ?
C7 C21 1.385(6) . ?
C7 C6 1.490(5) . ?
N1 C10 1.358(5) . ?
N1 C14 1.330(6) . ?
C21 H21 0.9300 . ?
C21 C20 1.385(5) . ?
C9 C10 1.483(6) . ?
C1 C6 1.398(6) . ?
C1 O1 1.354(5) . ?
C1 C2 1.403(6) . ?
C6 C5 1.382(6) . ?
C10 C11 1.369(6) . ?
C20 C19 1.475(6) . ?
O1 H1 0.8200 . ?
C2 C3 1.370(7) . ?
C19 C18 1.373(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.391(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.377(7) . ?
C3 H3 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.373(6) . ?
C14 H14 0.9300 . ?
C14 C13 1.377(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.362(7) . ?
C18 H18 0.9300 . ?
C18 C17 1.384(7) . ?
C13 H13 0.9300 . ?
C13 C12 1.378(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.358(7) . ?
C12 H12 0.9300 . ?
C17 H17 0.9300 . ?
Cl2 O2 1.357(6) . ?
Cl2 O4 1.342(6) . ?
Cl2 O5 1.589(8) . ?
Cl2 O3 1.359(7) . ?
Cl2 O4A 1.823(16) . ?
Cl2 O5A 1.263(15) . ?
Cl2 O3A 1.656(13) . ?
Cl2 O2A 1.409(16) . ?

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
N2 Cu1 N3 80.06(14) . . ?
N2 Cu1 N1 80.28(14) . . ?
N2 Cu1 Cl1 177.08(11) . . ?
N3 Cu1 Cl1 99.79(10) . . ?
N1 Cu1 N3 158.54(14) . . ?
N1 Cu1 Cl1 99.39(10) . . ?
C9 N2 Cu1 118.7(3) . . ?
C20 N2 Cu1 118.6(3) . . ?
C20 N2 C9 122.5(3) . . ?
C19 N3 Cu1 113.9(3) . . ?
C15 N3 Cu1 127.2(3) . . ?
C15 N3 C19 118.9(4) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C9 C8 C7 118.8(4) . . ?
C8 C7 C6 119.1(4) . . ?
C21 C7 C8 119.0(4) . . ?
C21 C7 C6 121.9(4) . . ?
C10 N1 Cu1 114.1(3) . . ?
C14 N1 Cu1 127.6(3) . . ?
C14 N1 C10 118.2(4) . . ?
C7 C21 H21 120.1 . . ?
C20 C21 C7 119.8(4) . . ?
C20 C21 H21 120.1 . . ?
N2 C9 C8 120.4(4) . . ?
N2 C9 C10 112.7(3) . . ?
C8 C9 C10 126.9(4) . . ?
C6 C1 C2 118.3(4) . . ?
O1 C1 C6 118.9(4) . . ?
O1 C1 C2 122.6(4) . . ?
C1 C6 C7 120.8(4) . . ?
C5 C6 C7 119.6(4) . . ?
C5 C6 C1 119.5(4) . . ?
N1 C10 C9 113.6(4) . . ?
N1 C10 C11 121.8(4) . . ?
C11 C10 C9 124.6(4) . . ?
N2 C20 C21 119.5(4) . . ?
N2 C20 C19 112.8(3) . . ?
C21 C20 C19 127.6(4) . . ?
C1 O1 H1 109.5 . . ?
C1 C2 Br1 119.3(4) . . ?
C3 C2 Br1 119.4(3) . . ?
C3 C2 C1 121.3(4) . . ?
N3 C19 C20 114.1(4) . . ?
N3 C19 C18 121.0(4) . . ?
C18 C19 C20 124.9(4) . . ?
C6 C5 H5 119.3 . . ?
C6 C5 C4 121.3(4) . . ?
C4 C5 H5 119.3 . . ?
C5 C4 H4 120.4 . . ?
C3 C4 C5 119.1(5) . . ?
C3 C4 H4 120.4 . . ?
C2 C3 C4 120.4(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.6(5) . . ?
C12 C11 H11 120.2 . . ?
N1 C14 H14 118.8 . . ?
N1 C14 C13 122.5(5) . . ?
C13 C14 H14 118.8 . . ?
N3 C15 H15 119.0 . . ?
N3 C15 C16 122.0(5) . . ?
C16 C15 H15 119.0 . . ?
C19 C18 H18 120.2 . . ?
C19 C18 C17 119.6(5) . . ?
C17 C18 H18 120.2 . . ?
C14 C13 H13 120.5 . . ?
C14 C13 C12 119.1(5) . . ?
C12 C13 H13 120.5 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.9(5) . . ?
C17 C16 H16 120.0 . . ?
C11 C12 C13 118.8(5) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C18 C17 H17 120.7 . . ?
C16 C17 C18 118.6(5) . . ?
C16 C17 H17 120.7 . . ?
O2 Cl2 O5 101.3(5) . . ?
O2 Cl2 O3 114.5(5) . . ?
O4 Cl2 O2 117.4(5) . . ?
O4 Cl2 O5 101.9(5) . . ?
O4 Cl2 O3 115.5(5) . . ?
O3 Cl2 O5 102.7(5) . . ?
O5A Cl2 O4A 103.0(11) . . ?
O5A Cl2 O3A 115.1(10) . . ?
O5A Cl2 O2A 138.1(12) . . ?
O3A Cl2 O4A 75.7(9) . . ?
O2A Cl2 O4A 97.6(10) . . ?
O2A Cl2 O3A 105.2(9) . . ?

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 N2 C9 C8 173.9(3) . . . . ?
Cu1 N2 C9 C10 -7.1(5) . . . . ?
Cu1 N2 C20 C21 -172.8(3) . . . . ?
Cu1 N2 C20 C19 8.2(5) . . . . ?
Cu1 N3 C19 C20 -1.2(5) . . . . ?
Cu1 N3 C19 C18 -179.5(4) . . . . ?
Cu1 N3 C15 C16 -179.2(4) . . . . ?
Cu1 N1 C10 C9 4.6(5) . . . . ?
Cu1 N1 C10 C11 -176.5(4) . . . . ?
Cu1 N1 C14 C13 176.6(4) . . . . ?
Br1 C2 C3 C4 -178.4(3) . . . . ?
N2 C9 C10 N1 1.3(5) . . . . ?
N2 C9 C10 C11 -177.6(4) . . . . ?
N2 C20 C19 N3 -4.2(6) . . . . ?
N2 C20 C19 C18 173.9(5) . . . . ?
N3 C19 C18 C17 -1.3(8) . . . . ?
N3 C15 C16 C17 -1.2(9) . . . . ?
C8 C7 C21 C20 -1.3(6) . . . . ?
C8 C7 C6 C1 140.9(4) . . . . ?
C8 C7 C6 C5 -39.6(6) . . . . ?
C8 C9 C10 N1 -179.8(4) . . . . ?
C8 C9 C10 C11 1.3(7) . . . . ?
C7 C8 C9 N2 -1.8(6) . . . . ?
C7 C8 C9 C10 179.3(4) . . . . ?
C7 C21 C20 N2 -0.4(6) . . . . ?
C7 C21 C20 C19 178.4(4) . . . . ?
C7 C6 C5 C4 -178.0(4) . . . . ?
N1 C10 C11 C12 -0.6(7) . . . . ?
N1 C14 C13 C12 -0.2(9) . . . . ?
C21 C7 C6 C1 -41.7(6) . . . . ?
C21 C7 C6 C5 137.8(5) . . . . ?
C21 C20 C19 N3 176.8(4) . . . . ?
C21 C20 C19 C18 -5.0(8) . . . . ?
C9 N2 C20 C21 1.0(6) . . . . ?
C9 N2 C20 C19 -178.0(4) . . . . ?
C9 C8 C7 C21 2.4(6) . . . . ?
C9 C8 C7 C6 179.8(4) . . . . ?
C9 C10 C11 C12 178.2(4) . . . . ?
C1 C6 C5 C4 1.5(7) . . . . ?
C1 C2 C3 C4 0.8(7) . . . . ?
C6 C7 C21 C20 -178.7(4) . . . . ?
C6 C1 C2 Br1 179.3(3) . . . . ?
C6 C1 C2 C3 0.1(7) . . . . ?
C6 C5 C4 C3 -0.7(7) . . . . ?
C10 N1 C14 C13 -1.0(8) . . . . ?
C10 C11 C12 C13 -0.6(8) . . . . ?
C20 N2 C9 C8 0.1(6) . . . . ?
C20 N2 C9 C10 179.1(4) . . . . ?
C20 C19 C18 C17 -179.4(5) . . . . ?
O1 C1 C6 C7 -5.3(6) . . . . ?
O1 C1 C6 C5 175.2(4) . . . . ?
O1 C1 C2 Br1 3.1(6) . . . . ?
O1 C1 C2 C3 -176.2(4) . . . . ?
C2 C1 C6 C7 178.3(4) . . . . ?
C2 C1 C6 C5 -1.2(6) . . . . ?
C19 N3 C15 C16 0.3(8) . . . . ?
C19 C18 C17 C16 0.4(9) . . . . ?
C5 C4 C3 C2 -0.5(7) . . . . ?
C14 N1 C10 C9 -177.5(4) . . . . ?
C14 N1 C10 C11 1.4(7) . . . . ?
C14 C13 C12 C11 1.0(9) . . . . ?
C15 N3 C19 C20 179.3(4) . . . . ?
C15 N3 C19 C18 1.0(7) . . . . ?
C15 C16 C17 C18 0.9(9) . . . . ?

_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 1.754
_oxdiff_exptl_absorpt_empirical_full_min 0.695
####################################################################### 
# 
# 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_20190422-czf-zyj-b19cu-1aaa
_database_code_depnum_ccdc_archive 'CCDC 2102155'
loop_
_audit_author_name
_audit_author_address
'Yunqiong Gu'
;Guangxi Normal University
China
;
_audit_update_record             
;
2021-08-09 deposited with the CCDC.	2021-12-08 downloaded from the CCDC.
;
_audit_creation_date             2021-07-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 Br Cl2 Cu N3 O, C H4 O'
_chemical_formula_sum            'C22 H18 Br Cl2 Cu N3 O2'
_chemical_formula_weight         570.74
_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'
Cl Cl 0.1484 0.1585 '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                   8.9058(4)
_cell_length_b                   10.7978(8)
_cell_length_c                   12.8382(7)
_cell_angle_alpha                107.217(6)
_cell_angle_beta                 109.817(5)
_cell_angle_gamma                92.642(5)
_cell_volume                     1094.57(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3304
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.0320
_cell_measurement_theta_min      3.5050
_shelx_estimated_absorpt_T_max   0.708
_shelx_estimated_absorpt_T_min   0.364
_exptl_absorpt_coefficient_mu    3.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light blue'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             570
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15782
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.419
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  86.00   1.00   10.00    --   17.61  57.00  60.00   90
  2  ω    -12.00  88.00   1.00   10.00    --   17.61  77.00-180.00  100
  3  ω    -20.00  60.00   1.00   10.00    --   17.61 -99.00 -60.00   80
  4  ω    -53.00  48.00   1.00   10.00    --   17.61 -77.00  60.00  101
  5  ω    -26.00  91.00   1.00   10.00    --   17.61  19.00   0.00  117
  6  ω     35.00  94.00   1.00   10.00    --   17.61 178.00 -90.00   59
  7  ω     35.00  94.00   1.00   10.00    --   17.61 178.00  90.00   59
  8  ω    -20.00  27.00   1.00   10.00    --   17.61 -99.00-180.00   47
  9  ω    -92.00   6.00   1.00   10.00    --  -19.88 -38.00  60.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0382083000
_diffrn_orient_matrix_UB_12      0.0485750000
_diffrn_orient_matrix_UB_13      0.0560775000
_diffrn_orient_matrix_UB_21      -0.0147707000
_diffrn_orient_matrix_UB_22      0.0499529000
_diffrn_orient_matrix_UB_23      -0.0260091000
_diffrn_orient_matrix_UB_31      -0.0753958000
_diffrn_orient_matrix_UB_32      0.0019036000
_diffrn_orient_matrix_UB_33      0.0073302000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\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                3253
_reflns_number_total             4467
_reflns_odcompleteness_completeness 99.80
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.889
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4467
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.060
_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)+(0.0402P)²+0.6649P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1108
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C15(H15), C11(H11), C17(H17), C5(H5), C18(H18), C21(H21), C13(H13),
 C3(H3), C14(H14), C16(H16), C0AA(H0AA), C12(H12)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O22(H22)
;
_atom_sites_solution_hydrogens   geom
_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 -0.62200(6) 0.86388(5) 0.12869(4) 0.03277(15) Uani 1 1 d . . . . .
Br1 Br 0.26395(5) 1.53543(5) 0.31400(4) 0.04446(16) Uani 1 1 d . . . . .
Cl1 Cl -0.87531(12) 0.78911(12) -0.00107(10) 0.0462(3) Uani 1 1 d . . . . .
Cl2 Cl -0.52545(15) 0.68573(13) 0.20262(11) 0.0526(3) Uani 1 1 d . . . . .
O1 O 0.0162(4) 1.2588(3) 0.5815(3) 0.0441(8) Uani 1 1 d . . . . .
H1 H 0.080813 1.278831 0.649271 0.066 Uiso 1 1 calc R U . . .
N1 N -0.5040(4) 0.8266(3) 0.0145(3) 0.0320(8) Uani 1 1 d . . . . .
N2 N -0.4315(4) 1.0015(3) 0.2140(3) 0.0296(8) Uani 1 1 d . . . . .
N3 N -0.6723(4) 0.9641(3) 0.2716(3) 0.0347(8) Uani 1 1 d . . . . .
C19 C -0.5543(5) 1.0638(4) 0.3533(3) 0.0312(9) Uani 1 1 d . . . . .
C8 C -0.1794(5) 1.0985(4) 0.2285(3) 0.0337(10) Uani 1 1 d . . . . .
H8 H -0.100898 1.101711 0.196212 0.040 Uiso 1 1 calc R U . . .
C10 C -0.3578(4) 0.9024(4) 0.0532(3) 0.0294(9) Uani 1 1 d . . . . .
C1 C 0.0722(5) 1.3228(4) 0.5235(4) 0.0336(9) Uani 1 1 d . . . . .
C20 C -0.4151(5) 1.0858(4) 0.3192(3) 0.0291(9) Uani 1 1 d . . . . .
C7 C -0.1579(5) 1.1881(4) 0.3384(3) 0.0300(9) Uani 1 1 d . . . . .
C9 C -0.3183(5) 1.0050(4) 0.1678(3) 0.0302(9) Uani 1 1 d . . . . .
C15 C -0.8010(5) 0.9329(5) 0.2951(4) 0.0431(11) Uani 1 1 d . . . . .
H15 H -0.882764 0.865505 0.238860 0.052 Uiso 1 1 calc R U . . .
C11 C -0.2579(5) 0.8808(4) -0.0097(4) 0.0370(10) Uani 1 1 d . . . . .
H11 H -0.158659 0.934772 0.017759 0.044 Uiso 1 1 calc R U . . .
C17 C -0.6976(5) 1.0978(4) 0.4825(4) 0.0413(11) Uani 1 1 d . . . . .
H17 H -0.706219 1.142589 0.553710 0.050 Uiso 1 1 calc R U . . .
C5 C 0.0493(5) 1.3522(4) 0.3399(4) 0.0348(10) Uani 1 1 d . . . . .
H5 H -0.003496 1.330285 0.259204 0.042 Uiso 1 1 calc R U . . .
C18 C -0.5646(5) 1.1325(4) 0.4589(4) 0.0364(10) Uani 1 1 d . . . . .
H18 H -0.483283 1.201280 0.513486 0.044 Uiso 1 1 calc R U . . .
C4 C 0.1874(5) 1.4462(4) 0.3979(4) 0.0363(10) Uani 1 1 d . . . . .
C21 C -0.2780(5) 1.1793(4) 0.3843(3) 0.0323(9) Uani 1 1 d . . . . .
H21 H -0.265708 1.235989 0.458069 0.039 Uiso 1 1 calc R U . . .
C13 C -0.4544(5) 0.6993(5) -0.1526(4) 0.0434(11) Uani 1 1 d . . . . .
H13 H -0.488937 0.628667 -0.222362 0.052 Uiso 1 1 calc R U . . .
C3 C 0.2708(5) 1.4753(4) 0.5166(4) 0.0401(11) Uani 1 1 d . . . . .
H3 H 0.366275 1.535656 0.554463 0.048 Uiso 1 1 calc R U . . .
C6 C -0.0112(4) 1.2899(4) 0.4023(3) 0.0310(9) Uani 1 1 d . . . . .
C14 C -0.5491(5) 0.7269(4) -0.0865(4) 0.0396(11) Uani 1 1 d . . . . .
H14 H -0.648992 0.674036 -0.113204 0.048 Uiso 1 1 calc R U . . .
C16 C -0.8169(5) 0.9973(5) 0.4005(4) 0.0447(12) Uani 1 1 d . . . . .
H16 H -0.907021 0.972643 0.415367 0.054 Uiso 1 1 calc R U . . .
C0AA C 0.2132(5) 1.4152(4) 0.5789(4) 0.0405(11) Uani 1 1 d . . . . .
H0AA H 0.268943 1.436492 0.659223 0.049 Uiso 1 1 calc R U . . .
C12 C -0.3072(6) 0.7780(5) -0.1138(4) 0.0460(12) Uani 1 1 d . . . . .
H12 H -0.241542 0.761861 -0.157643 0.055 Uiso 1 1 calc R U . . .
O22 O 0.1841(4) 1.3083(5) 0.8043(3) 0.0849(14) Uani 1 1 d . . . . .
H22 H 0.278069 1.318640 0.808553 0.127 Uiso 1 1 calc R U . . .
C2 C 0.1648(8) 1.4118(6) 0.9010(5) 0.0832(19) Uani 1 1 d . . . . .
H2A H 0.111463 1.476537 0.871555 0.125 Uiso 1 1 calc R U . . .
H2B H 0.269328 1.452686 0.960069 0.125 Uiso 1 1 calc R U . . .
H2C H 0.101144 1.373890 0.934383 0.125 Uiso 1 1 calc R U . . .


_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 Cl1 2.2370(11) . ?
Cu1 Cl2 2.4536(13) . ?
Cu1 N1 2.037(3) . ?
Cu1 N2 1.957(3) . ?
Cu1 N3 2.040(3) . ?
Br1 C4 1.898(4) . ?
O1 H1 0.8200 . ?
O1 C1 1.344(5) . ?
N1 C10 1.355(5) . ?
N1 C14 1.335(5) . ?
N2 C20 1.342(5) . ?
N2 C9 1.335(5) . ?
N3 C19 1.358(5) . ?
N3 C15 1.334(5) . ?
C19 C20 1.479(5) . ?
C19 C18 1.375(5) . ?
C8 H8 0.9300 . ?
C8 C7 1.397(5) . ?
C8 C9 1.387(5) . ?
C10 C9 1.471(5) . ?
C10 C11 1.375(5) . ?
C1 C6 1.401(5) . ?
C1 C0AA 1.392(6) . ?
C20 C21 1.379(5) . ?
C7 C21 1.397(5) . ?
C7 C6 1.482(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(6) . ?
C17 C16 1.369(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.383(6) . ?
C5 C6 1.401(5) . ?
C18 H18 0.9300 . ?
C4 C3 1.379(6) . ?
C21 H21 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.371(6) . ?
C13 C12 1.376(6) . ?
C3 H3 0.9300 . ?
C3 C0AA 1.371(6) . ?
C14 H14 0.9300 . ?
C16 H16 0.9300 . ?
C0AA H0AA 0.9300 . ?
C12 H12 0.9300 . ?
O22 H22 0.8200 . ?
O22 C2 1.469(7) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?

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
Cl1 Cu1 Cl2 107.45(5) . . ?
N1 Cu1 Cl1 98.62(9) . . ?
N1 Cu1 Cl2 92.70(10) . . ?
N1 Cu1 N3 157.64(13) . . ?
N2 Cu1 Cl1 151.39(10) . . ?
N2 Cu1 Cl2 101.14(10) . . ?
N2 Cu1 N1 78.89(13) . . ?
N2 Cu1 N3 79.08(13) . . ?
N3 Cu1 Cl1 98.85(10) . . ?
N3 Cu1 Cl2 95.26(10) . . ?
C1 O1 H1 109.5 . . ?
C10 N1 Cu1 115.3(3) . . ?
C14 N1 Cu1 126.0(3) . . ?
C14 N1 C10 118.2(3) . . ?
C20 N2 Cu1 119.1(3) . . ?
C9 N2 Cu1 118.9(3) . . ?
C9 N2 C20 122.0(3) . . ?
C19 N3 Cu1 115.1(3) . . ?
C15 N3 Cu1 126.0(3) . . ?
C15 N3 C19 118.6(4) . . ?
N3 C19 C20 113.6(3) . . ?
N3 C19 C18 121.7(4) . . ?
C18 C19 C20 124.6(4) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C9 C8 C7 119.8(4) . . ?
N1 C10 C9 113.3(3) . . ?
N1 C10 C11 121.9(4) . . ?
C11 C10 C9 124.9(4) . . ?
O1 C1 C6 118.3(4) . . ?
O1 C1 C0AA 122.1(4) . . ?
C0AA C1 C6 119.6(4) . . ?
N2 C20 C19 112.9(3) . . ?
N2 C20 C21 120.5(3) . . ?
C21 C20 C19 126.6(4) . . ?
C8 C7 C6 119.9(4) . . ?
C21 C7 C8 118.3(4) . . ?
C21 C7 C6 121.8(4) . . ?
N2 C9 C8 120.0(4) . . ?
N2 C9 C10 113.5(3) . . ?
C8 C9 C10 126.6(4) . . ?
N3 C15 H15 118.9 . . ?
N3 C15 C16 122.2(4) . . ?
C16 C15 H15 118.9 . . ?
C10 C11 H11 120.6 . . ?
C12 C11 C10 118.9(4) . . ?
C12 C11 H11 120.6 . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.7(4) . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.3(4) . . ?
C6 C5 H5 119.9 . . ?
C19 C18 C17 118.9(4) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C5 C4 Br1 120.1(3) . . ?
C3 C4 Br1 119.6(3) . . ?
C3 C4 C5 120.4(4) . . ?
C20 C21 C7 119.4(4) . . ?
C20 C21 H21 120.3 . . ?
C7 C21 H21 120.3 . . ?
C14 C13 H13 120.7 . . ?
C14 C13 C12 118.7(4) . . ?
C12 C13 H13 120.7 . . ?
C4 C3 H3 120.0 . . ?
C0AA C3 C4 120.0(4) . . ?
C0AA C3 H3 120.0 . . ?
C1 C6 C7 121.6(4) . . ?
C5 C6 C1 118.9(4) . . ?
C5 C6 C7 119.5(4) . . ?
N1 C14 C13 122.7(4) . . ?
N1 C14 H14 118.6 . . ?
C13 C14 H14 118.6 . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.8(4) . . ?
C17 C16 H16 120.6 . . ?
C1 C0AA H0AA 119.6 . . ?
C3 C0AA C1 120.9(4) . . ?
C3 C0AA H0AA 119.6 . . ?
C11 C12 C13 119.6(4) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C2 O22 H22 109.5 . . ?
O22 C2 H2A 109.5 . . ?
O22 C2 H2B 109.5 . . ?
O22 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

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 N1 C10 C9 -4.5(4) . . . . ?
Cu1 N1 C10 C11 174.1(3) . . . . ?
Cu1 N1 C14 C13 -172.5(3) . . . . ?
Cu1 N2 C20 C19 -2.7(4) . . . . ?
Cu1 N2 C20 C21 176.5(3) . . . . ?
Cu1 N2 C9 C8 -177.7(3) . . . . ?
Cu1 N2 C9 C10 1.6(4) . . . . ?
Cu1 N3 C19 C20 3.6(4) . . . . ?
Cu1 N3 C19 C18 -174.2(3) . . . . ?
Cu1 N3 C15 C16 172.5(3) . . . . ?
Br1 C4 C3 C0AA 177.4(3) . . . . ?
O1 C1 C6 C7 0.3(6) . . . . ?
O1 C1 C6 C5 -177.6(4) . . . . ?
O1 C1 C0AA C3 177.5(4) . . . . ?
N1 C10 C9 N2 2.0(5) . . . . ?
N1 C10 C9 C8 -178.8(4) . . . . ?
N1 C10 C11 C12 -1.0(6) . . . . ?
N2 C20 C21 C7 1.8(6) . . . . ?
N3 C19 C20 N2 -0.8(5) . . . . ?
N3 C19 C20 C21 -179.8(4) . . . . ?
N3 C19 C18 C17 0.8(6) . . . . ?
N3 C15 C16 C17 1.1(7) . . . . ?
C19 N3 C15 C16 -0.9(6) . . . . ?
C19 C20 C21 C7 -179.2(4) . . . . ?
C8 C7 C21 C20 -1.7(6) . . . . ?
C8 C7 C6 C1 -138.5(4) . . . . ?
C8 C7 C6 C5 39.4(6) . . . . ?
C10 N1 C14 C13 -0.5(6) . . . . ?
C10 C11 C12 C13 -0.1(7) . . . . ?
C20 N2 C9 C8 -0.6(6) . . . . ?
C20 N2 C9 C10 178.7(3) . . . . ?
C20 C19 C18 C17 -176.7(4) . . . . ?
C7 C8 C9 N2 0.6(6) . . . . ?
C7 C8 C9 C10 -178.6(4) . . . . ?
C9 N2 C20 C19 -179.7(3) . . . . ?
C9 N2 C20 C21 -0.6(6) . . . . ?
C9 C8 C7 C21 0.6(6) . . . . ?
C9 C8 C7 C6 -178.7(4) . . . . ?
C9 C10 C11 C12 177.5(4) . . . . ?
C15 N3 C19 C20 177.7(3) . . . . ?
C15 N3 C19 C18 -0.1(6) . . . . ?
C11 C10 C9 N2 -176.6(4) . . . . ?
C11 C10 C9 C8 2.7(6) . . . . ?
C5 C4 C3 C0AA -2.9(7) . . . . ?
C18 C19 C20 N2 176.9(4) . . . . ?
C18 C19 C20 C21 -2.1(6) . . . . ?
C18 C17 C16 C15 -0.2(7) . . . . ?
C4 C5 C6 C1 -1.2(6) . . . . ?
C4 C5 C6 C7 -179.1(4) . . . . ?
C4 C3 C0AA C1 1.2(7) . . . . ?
C21 C7 C6 C1 42.3(6) . . . . ?
C21 C7 C6 C5 -139.9(4) . . . . ?
C6 C1 C0AA C3 0.5(7) . . . . ?
C6 C7 C21 C20 177.5(4) . . . . ?
C6 C5 C4 Br1 -177.4(3) . . . . ?
C6 C5 C4 C3 2.9(6) . . . . ?
C14 N1 C10 C9 -177.3(3) . . . . ?
C14 N1 C10 C11 1.3(6) . . . . ?
C14 C13 C12 C11 0.8(7) . . . . ?
C16 C17 C18 C19 -0.7(6) . . . . ?
C0AA C1 C6 C7 177.4(4) . . . . ?
C0AA C1 C6 C5 -0.5(6) . . . . ?
C12 C13 C14 N1 -0.5(7) . . . . ?

_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 1.738
_oxdiff_exptl_absorpt_empirical_full_min 0.688
