# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_chw1059
_database_code_depnum_ccdc_archive 'CCDC 2261958'
loop_
_audit_author_name
_audit_author_address
'Vladimir Arion'
;University of Vienna
Austria
;
_audit_update_record             
;
2023-05-10 deposited with the CCDC.	2023-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H23 Cl2 Cu N5, 2(C3 H7 N O)'
_chemical_formula_sum            'C31 H37 Cl2 Cu N7 O2'
_chemical_formula_weight         674.11

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'
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'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   8.8925(5)
_cell_length_b                   21.1262(10)
_cell_length_c                   34.302(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.643(5)
_cell_angle_gamma                90
_cell_volume                     6422.9(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    21779
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      65.01

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             2808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.026
_exptl_crystal_size_min          0.016
_exptl_absorpt_coefficient_mu    2.812
_shelx_estimated_absorpt_T_min   0.334
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1729
_exptl_absorpt_correction_T_max  0.9426
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Primux 100 micro'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            53100
_diffrn_reflns_av_unetI/netI     0.0795
_diffrn_reflns_av_R_equivalents  0.1805
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.585
_diffrn_reflns_theta_max         64.768
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.912
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.912
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.912
_reflns_number_total             5319
_reflns_number_gt                3257
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)'
_computing_cell_refinement       'X-Area Recipe 1.36.0-0 (STOE, 2020)'
_computing_data_reduction        
'X-Area Integrate 1.78.3.0; X-Area LANA 1.83.8.0 (STOE, 2020)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1258P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5319
_refine_ls_number_parameters     393
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1282
_refine_ls_R_factor_gt           0.0751
_refine_ls_wR_factor_ref         0.2103
_refine_ls_wR_factor_gt          0.1787
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Cu Cu 0.72401(9) 0.54151(4) 0.56980(3) 0.0332(3) Uani 1 1 d . . . . .
Cl1 Cl 0.81957(15) 0.44330(7) 0.58202(4) 0.0372(4) Uani 1 1 d . . . . .
Cl2 Cl 0.94308(15) 0.60805(8) 0.57095(5) 0.0388(4) Uani 1 1 d . . . . .
O1 O 0.2867(4) 0.7188(2) 0.58716(13) 0.0396(11) Uani 1 1 d . . . . .
O2 O 0.6353(5) 0.7771(2) 0.62494(13) 0.0451(12) Uani 1 1 d . . . . .
N19 N 0.7015(5) 0.5348(2) 0.51017(15) 0.0295(11) Uani 1 1 d . . . . .
N16 N 0.5452(5) 0.5967(2) 0.55652(14) 0.0325(12) Uani 1 1 d . . . . .
N8 N 0.6640(5) 0.5636(2) 0.62305(15) 0.0346(12) Uani 1 1 d . . . . .
N10 N 0.4866(5) 0.6914(3) 0.66677(15) 0.0372(13) Uani 1 1 d . . . . .
H10 H 0.5379 0.7208 0.6555 0.045 Uiso 1 1 calc R U . . .
N15 N 0.4826(5) 0.6212(2) 0.58707(15) 0.0332(12) Uani 1 1 d . . . . .
H15 H 0.4038 0.6465 0.5845 0.040 Uiso 1 1 calc R U . . .
N32 N 0.1042(5) 0.7448(2) 0.62736(15) 0.0349(12) Uani 1 1 d . . . . .
N31 N 0.6252(5) 0.7962(3) 0.55948(16) 0.0391(13) Uani 1 1 d . . . . .
C20 C 0.7914(6) 0.5036(3) 0.48741(19) 0.0346(15) Uani 1 1 d . . . . .
H20 H 0.8697 0.4782 0.4996 0.042 Uiso 1 1 calc R U . . .
C21 C 0.7764(6) 0.5065(3) 0.4467(2) 0.0378(15) Uani 1 1 d . . . . .
H21 H 0.8435 0.4842 0.4314 0.045 Uiso 1 1 calc R U . . .
C22 C 0.6594(7) 0.5433(3) 0.42906(19) 0.0389(15) Uani 1 1 d . . . . .
H22 H 0.6450 0.5464 0.4014 0.047 Uiso 1 1 calc R U . . .
C23 C 0.5648(6) 0.5751(3) 0.45246(18) 0.0345(15) Uani 1 1 d . . . . .
H23 H 0.4829 0.5993 0.4409 0.041 Uiso 1 1 calc R U . . .
C18 C 0.5895(6) 0.5716(3) 0.49277(19) 0.0317(14) Uani 1 1 d . . . . .
C17 C 0.4983(6) 0.6043(3) 0.51994(17) 0.0319(14) Uani 1 1 d . . . . .
C24 C 0.3651(6) 0.6446(3) 0.50665(19) 0.0386(15) Uani 1 1 d . . . . .
H24A H 0.3991 0.6879 0.5020 0.058 Uiso 1 1 calc R U . . .
H24B H 0.2935 0.6451 0.5269 0.058 Uiso 1 1 calc R U . . .
H24C H 0.3158 0.6272 0.4824 0.058 Uiso 1 1 calc R U . . .
C9 C 0.5516(6) 0.6036(3) 0.62339(16) 0.0285(13) Uani 1 1 d . . . . .
C9A C 0.4845(6) 0.6286(3) 0.65743(17) 0.0319(14) Uani 1 1 d . U . . .
C10A C 0.3952(7) 0.7010(3) 0.69669(18) 0.0360(15) Uani 1 1 d . U . . .
C14A C 0.3345(6) 0.6423(3) 0.70640(18) 0.0360(15) Uani 1 1 d . . . . .
C14B C 0.3922(6) 0.5961(3) 0.68097(18) 0.0329(14) Uani 1 1 d . U . . .
C7 C 0.7602(6) 0.5522(3) 0.65945(18) 0.0377(15) Uani 1 1 d . . . . .
H7A H 0.7451 0.5876 0.6776 0.045 Uiso 1 1 calc R U . . .
H7B H 0.8669 0.5535 0.6532 0.045 Uiso 1 1 calc R U . . .
C6 C 0.7349(6) 0.4912(3) 0.68053(19) 0.0399(16) Uani 1 1 d . . . . .
H6A H 0.8303 0.4793 0.6957 0.048 Uiso 1 1 calc R U . . .
H6B H 0.7118 0.4577 0.6608 0.048 Uiso 1 1 calc R U . . .
C5 C 0.6077(6) 0.4920(3) 0.70871(19) 0.0399(16) Uani 1 1 d . . . . .
H5A H 0.6314 0.4599 0.7293 0.048 Uiso 1 1 calc R U . . .
H5B H 0.6080 0.5339 0.7216 0.048 Uiso 1 1 calc R U . . .
C4A C 0.4494(6) 0.4793(3) 0.69011(18) 0.0364(15) Uani 1 1 d . . . . .
C14C C 0.3502(6) 0.5282(3) 0.67792(18) 0.0376(15) Uani 1 1 d . . . . .
C1 C 0.2011(6) 0.5127(4) 0.66316(18) 0.0393(16) Uani 1 1 d . . . . .
H1 H 0.1327 0.5457 0.6551 0.047 Uiso 1 1 calc R U . . .
C2 C 0.1546(7) 0.4514(3) 0.6603(2) 0.0440(17) Uani 1 1 d . . . . .
H2 H 0.0550 0.4419 0.6498 0.053 Uiso 1 1 calc R U . . .
C3 C 0.2515(7) 0.4030(4) 0.6726(2) 0.0452(17) Uani 1 1 d . . . . .
H3 H 0.2185 0.3602 0.6710 0.054 Uiso 1 1 calc R U . . .
C4 C 0.3970(7) 0.4174(3) 0.68713(19) 0.0416(16) Uani 1 1 d . . . . .
H4 H 0.4633 0.3839 0.6954 0.050 Uiso 1 1 calc R U . . .
C11 C 0.3593(7) 0.7566(4) 0.7163(2) 0.0454(18) Uani 1 1 d . . . . .
H11 H 0.4006 0.7963 0.7097 0.054 Uiso 1 1 calc R U . . .
C12 C 0.2625(7) 0.7516(4) 0.7452(2) 0.051(2) Uani 1 1 d . . . . .
H12 H 0.2357 0.7886 0.7588 0.061 Uiso 1 1 calc R U . . .
C13 C 0.2021(7) 0.6930(4) 0.7552(2) 0.0460(18) Uani 1 1 d . . . . .
H13 H 0.1359 0.6911 0.7755 0.055 Uiso 1 1 calc R U . . .
C14 C 0.2360(7) 0.6391(4) 0.73644(19) 0.0430(17) Uani 1 1 d . . . . .
H14 H 0.1940 0.5998 0.7435 0.052 Uiso 1 1 calc R U . . .
C30 C 0.1920(6) 0.7052(3) 0.61030(18) 0.0339(14) Uani 1 1 d . . . . .
H30 H 0.1816 0.6616 0.6163 0.041 Uiso 1 1 calc R U . . .
C28 C 0.0007(7) 0.7242(3) 0.6551(2) 0.0434(17) Uani 1 1 d . . . . .
H28A H 0.0367 0.7386 0.6814 0.065 Uiso 1 1 calc R U . . .
H28B H -0.0056 0.6779 0.6548 0.065 Uiso 1 1 calc R U . . .
H28C H -0.0994 0.7421 0.6479 0.065 Uiso 1 1 calc R U . . .
C29 C 0.1188(9) 0.8125(4) 0.6215(2) 0.057(2) Uani 1 1 d . . . . .
H29A H 0.1693 0.8317 0.6450 0.086 Uiso 1 1 calc R U . . .
H29B H 0.0184 0.8312 0.6163 0.086 Uiso 1 1 calc R U . . .
H29C H 0.1785 0.8202 0.5992 0.086 Uiso 1 1 calc R U . . .
C27 C 0.5805(7) 0.8043(3) 0.5947(2) 0.0395(16) Uani 1 1 d . . . . .
H27 H 0.5000 0.8331 0.5974 0.047 Uiso 1 1 calc R U . . .
C26 C 0.5575(7) 0.8305(3) 0.5261(2) 0.0434(16) Uani 1 1 d . . . . .
H26A H 0.4808 0.8595 0.5346 0.065 Uiso 1 1 calc R U . . .
H26B H 0.5103 0.8005 0.5071 0.065 Uiso 1 1 calc R U . . .
H26C H 0.6355 0.8546 0.5140 0.065 Uiso 1 1 calc R U . . .
C25 C 0.7451(7) 0.7512(4) 0.5528(2) 0.0508(19) Uani 1 1 d . . . . .
H25A H 0.7723 0.7275 0.5770 0.076 Uiso 1 1 calc R U . . .
H25B H 0.8337 0.7741 0.5451 0.076 Uiso 1 1 calc R U . . .
H25C H 0.7099 0.7217 0.5320 0.076 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
Cu N16 1.994(5) . ?
Cu N8 1.999(5) . ?
Cu N19 2.044(5) . ?
Cu Cl1 2.2683(18) . ?
Cu Cl2 2.4001(16) . ?
O1 C30 1.237(7) . ?
O2 C27 1.250(8) . ?
N19 C20 1.335(8) . ?
N19 C18 1.363(8) . ?
N16 C17 1.300(7) . ?
N16 N15 1.331(7) . ?
N8 C9 1.309(7) . ?
N8 C7 1.475(7) . ?
N10 C9A 1.364(8) . ?
N10 C10A 1.375(8) . ?
N10 H10 0.8800 . ?
N15 C9 1.394(7) . ?
N15 H15 0.8800 . ?
N32 C30 1.314(8) . ?
N32 C28 1.443(8) . ?
N32 C29 1.450(9) . ?
N31 C27 1.311(8) . ?
N31 C26 1.443(8) . ?
N31 C25 1.461(8) . ?
C20 C21 1.394(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.396(9) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(9) . ?
C22 H22 0.9500 . ?
C23 C18 1.384(8) . ?
C23 H23 0.9500 . ?
C18 C17 1.458(8) . ?
C17 C24 1.499(8) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C9 C9A 1.453(8) . ?
C9A C14B 1.380(9) . ?
C10A C11 1.402(9) . ?
C10A C14A 1.404(9) . ?
C14A C14 1.407(9) . ?
C14A C14B 1.431(9) . ?
C14B C14C 1.483(9) . ?
C7 C6 1.505(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C6 C5 1.546(9) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C5 C4A 1.522(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C4A C4 1.389(10) . ?
C4A C14C 1.401(9) . ?
C14C C1 1.419(8) . ?
C1 C2 1.361(10) . ?
C1 H1 0.9500 . ?
C2 C3 1.381(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(9) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C11 C12 1.370(10) . ?
C11 H11 0.9500 . ?
C12 C13 1.404(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.353(10) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C30 H30 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C27 H27 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

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
N16 Cu N8 78.8(2) . . ?
N16 Cu N19 78.47(19) . . ?
N8 Cu N19 156.74(19) . . ?
N16 Cu Cl1 148.94(15) . . ?
N8 Cu Cl1 99.70(16) . . ?
N19 Cu Cl1 97.26(14) . . ?
N16 Cu Cl2 107.02(15) . . ?
N8 Cu Cl2 97.15(15) . . ?
N19 Cu Cl2 94.06(13) . . ?
Cl1 Cu Cl2 103.96(6) . . ?
C20 N19 C18 118.4(5) . . ?
C20 N19 Cu 127.2(4) . . ?
C18 N19 Cu 114.0(4) . . ?
C17 N16 N15 126.1(5) . . ?
C17 N16 Cu 118.8(4) . . ?
N15 N16 Cu 115.1(3) . . ?
C9 N8 C7 119.2(5) . . ?
C9 N8 Cu 114.8(4) . . ?
C7 N8 Cu 123.8(4) . . ?
C9A N10 C10A 108.8(5) . . ?
C9A N10 H10 125.6 . . ?
C10A N10 H10 125.6 . . ?
N16 N15 C9 114.7(5) . . ?
N16 N15 H15 122.7 . . ?
C9 N15 H15 122.7 . . ?
C30 N32 C28 122.3(6) . . ?
C30 N32 C29 120.2(6) . . ?
C28 N32 C29 117.2(5) . . ?
C27 N31 C26 121.8(5) . . ?
C27 N31 C25 120.5(6) . . ?
C26 N31 C25 117.7(6) . . ?
N19 C20 C21 123.5(6) . . ?
N19 C20 H20 118.3 . . ?
C21 C20 H20 118.3 . . ?
C20 C21 C22 117.7(6) . . ?
C20 C21 H21 121.1 . . ?
C22 C21 H21 121.1 . . ?
C23 C22 C21 119.1(6) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C22 C23 C18 120.0(6) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
N19 C18 C23 121.2(5) . . ?
N19 C18 C17 114.5(5) . . ?
C23 C18 C17 124.2(5) . . ?
N16 C17 C18 114.0(5) . . ?
N16 C17 C24 123.3(6) . . ?
C18 C17 C24 122.8(5) . . ?
C17 C24 H24A 109.5 . . ?
C17 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C17 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N8 C9 N15 116.5(5) . . ?
N8 C9 C9A 127.2(5) . . ?
N15 C9 C9A 116.2(5) . . ?
N10 C9A C14B 110.1(5) . . ?
N10 C9A C9 122.9(6) . . ?
C14B C9A C9 126.3(6) . . ?
N10 C10A C11 130.8(6) . . ?
N10 C10A C14A 107.9(5) . . ?
C11 C10A C14A 121.3(6) . . ?
C14 C14A C10A 119.3(6) . . ?
C14 C14A C14B 133.6(6) . . ?
C10A C14A C14B 107.1(5) . . ?
C9A C14B C14A 106.1(6) . . ?
C9A C14B C14C 126.7(6) . . ?
C14A C14B C14C 126.9(6) . . ?
N8 C7 C6 116.6(5) . . ?
N8 C7 H7A 108.1 . . ?
C6 C7 H7A 108.1 . . ?
N8 C7 H7B 108.1 . . ?
C6 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
C7 C6 C5 115.8(5) . . ?
C7 C6 H6A 108.3 . . ?
C5 C6 H6A 108.3 . . ?
C7 C6 H6B 108.3 . . ?
C5 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
C4A C5 C6 115.8(5) . . ?
C4A C5 H5A 108.3 . . ?
C6 C5 H5A 108.3 . . ?
C4A C5 H5B 108.3 . . ?
C6 C5 H5B 108.3 . . ?
H5A C5 H5B 107.4 . . ?
C4 C4A C14C 118.3(6) . . ?
C4 C4A C5 119.4(6) . . ?
C14C C4A C5 122.2(6) . . ?
C4A C14C C1 118.9(6) . . ?
C4A C14C C14B 122.9(5) . . ?
C1 C14C C14B 118.1(6) . . ?
C2 C1 C14C 121.0(6) . . ?
C2 C1 H1 119.5 . . ?
C14C C1 H1 119.5 . . ?
C1 C2 C3 120.3(6) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 119.3(7) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C4A 122.2(6) . . ?
C3 C4 H4 118.9 . . ?
C4A C4 H4 118.9 . . ?
C12 C11 C10A 117.7(7) . . ?
C12 C11 H11 121.2 . . ?
C10A C11 H11 121.2 . . ?
C11 C12 C13 121.3(7) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 121.5(7) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C14A 118.9(7) . . ?
C13 C14 H14 120.6 . . ?
C14A C14 H14 120.6 . . ?
O1 C30 N32 126.6(6) . . ?
O1 C30 H30 116.7 . . ?
N32 C30 H30 116.7 . . ?
N32 C28 H28A 109.5 . . ?
N32 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N32 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N32 C29 H29A 109.5 . . ?
N32 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N32 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O2 C27 N31 125.4(6) . . ?
O2 C27 H27 117.3 . . ?
N31 C27 H27 117.3 . . ?
N31 C26 H26A 109.5 . . ?
N31 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N31 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N31 C25 H25A 109.5 . . ?
N31 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N31 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C17 N16 N15 C9 177.5(5) . . . . ?
Cu N16 N15 C9 -0.7(6) . . . . ?
C18 N19 C20 C21 -0.3(9) . . . . ?
Cu N19 C20 C21 -173.5(5) . . . . ?
N19 C20 C21 C22 -1.0(9) . . . . ?
C20 C21 C22 C23 0.2(9) . . . . ?
C21 C22 C23 C18 1.9(9) . . . . ?
C20 N19 C18 C23 2.5(8) . . . . ?
Cu N19 C18 C23 176.5(4) . . . . ?
C20 N19 C18 C17 -179.3(5) . . . . ?
Cu N19 C18 C17 -5.3(6) . . . . ?
C22 C23 C18 N19 -3.3(9) . . . . ?
C22 C23 C18 C17 178.7(6) . . . . ?
N15 N16 C17 C18 -179.9(5) . . . . ?
Cu N16 C17 C18 -1.7(7) . . . . ?
N15 N16 C17 C24 1.8(10) . . . . ?
Cu N16 C17 C24 179.9(5) . . . . ?
N19 C18 C17 N16 4.7(8) . . . . ?
C23 C18 C17 N16 -177.2(6) . . . . ?
N19 C18 C17 C24 -177.0(5) . . . . ?
C23 C18 C17 C24 1.1(9) . . . . ?
C7 N8 C9 N15 168.5(5) . . . . ?
Cu N8 C9 N15 4.7(7) . . . . ?
C7 N8 C9 C9A -15.7(9) . . . . ?
Cu N8 C9 C9A -179.5(5) . . . . ?
N16 N15 C9 N8 -2.7(7) . . . . ?
N16 N15 C9 C9A -178.9(5) . . . . ?
C10A N10 C9A C14B 0.0(6) . . . . ?
C10A N10 C9A C9 171.0(5) . . . . ?
N8 C9 C9A N10 117.1(7) . . . . ?
N15 C9 C9A N10 -67.1(7) . . . . ?
N8 C9 C9A C14B -73.4(8) . . . . ?
N15 C9 C9A C14B 102.4(7) . . . . ?
C9A N10 C10A C11 -179.5(6) . . . . ?
C9A N10 C10A C14A 0.1(6) . . . . ?
N10 C10A C14A C14 -179.9(5) . . . . ?
C11 C10A C14A C14 -0.2(8) . . . . ?
N10 C10A C14A C14B -0.2(6) . . . . ?
C11 C10A C14A C14B 179.5(5) . . . . ?
N10 C9A C14B C14A -0.1(6) . . . . ?
C9 C9A C14B C14A -170.7(5) . . . . ?
N10 C9A C14B C14C 174.6(5) . . . . ?
C9 C9A C14B C14C 4.0(9) . . . . ?
C14 C14A C14B C9A 179.8(6) . . . . ?
C10A C14A C14B C9A 0.2(6) . . . . ?
C14 C14A C14B C14C 5.1(10) . . . . ?
C10A C14A C14B C14C -174.5(6) . . . . ?
C9 N8 C7 C6 103.8(7) . . . . ?
Cu N8 C7 C6 -94.0(6) . . . . ?
N8 C7 C6 C5 -84.9(7) . . . . ?
C7 C6 C5 C4A 85.0(7) . . . . ?
C6 C5 C4A C4 89.1(8) . . . . ?
C6 C5 C4A C14C -94.9(7) . . . . ?
C4 C4A C14C C1 0.1(9) . . . . ?
C5 C4A C14C C1 -176.0(6) . . . . ?
C4 C4A C14C C14B 177.9(6) . . . . ?
C5 C4A C14C C14B 1.9(9) . . . . ?
C9A C14B C14C C4A 75.1(8) . . . . ?
C14A C14B C14C C4A -111.2(7) . . . . ?
C9A C14B C14C C1 -107.0(7) . . . . ?
C14A C14B C14C C1 66.6(8) . . . . ?
C4A C14C C1 C2 -0.8(9) . . . . ?
C14B C14C C1 C2 -178.8(6) . . . . ?
C14C C1 C2 C3 1.3(10) . . . . ?
C1 C2 C3 C4 -1.1(10) . . . . ?
C2 C3 C4 C4A 0.4(10) . . . . ?
C14C C4A C4 C3 0.1(10) . . . . ?
C5 C4A C4 C3 176.3(6) . . . . ?
N10 C10A C11 C12 179.5(6) . . . . ?
C14A C10A C11 C12 -0.1(9) . . . . ?
C10A C11 C12 C13 0.4(9) . . . . ?
C11 C12 C13 C14 -0.5(10) . . . . ?
C12 C13 C14 C14A 0.2(9) . . . . ?
C10A C14A C14 C13 0.2(8) . . . . ?
C14B C14A C14 C13 -179.4(6) . . . . ?
C28 N32 C30 O1 -177.7(6) . . . . ?
C29 N32 C30 O1 -3.5(9) . . . . ?
C26 N31 C27 O2 -178.8(6) . . . . ?
C25 N31 C27 O2 2.0(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N10 H10 O2 0.88 1.85 2.720(7) 171.5 .
N15 H15 O1 0.88 1.86 2.700(6) 160.3 .
C20 H20 Cl1 0.95 2.99 3.477(7) 113.3 .
C21 H21 Cl2 0.95 2.73 3.562(6) 147.3 5_766
C23 H23 Cl1 0.95 2.88 3.547(6) 127.8 5_666
C24 H24B O1 0.98 2.59 3.299(8) 129.0 .
C24 H24C Cl1 0.98 2.85 3.820(7) 170.5 5_666
C6 H6B Cl1 0.99 2.95 3.663(7) 129.4 .
C30 H30 Cl2 0.95 2.77 3.232(6) 110.9 1_455
C28 H28C O2 0.98 2.54 3.512(8) 173.5 1_455
C29 H29C Cl1 0.98 2.97 3.613(8) 124.5 3_455
C27 H27 Cl1 0.95 2.85 3.747(7) 157.3 3_455
C26 H26A Cl1 0.98 2.86 3.807(7) 161.6 3_455
C25 H25A Cl2 0.98 2.96 3.529(7) 117.9 .

_refine_diff_density_max         0.902
_refine_diff_density_min         -0.821
_refine_diff_density_rms         0.120

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_chwi185e
_database_code_depnum_ccdc_archive 'CCDC 2261959'
loop_
_audit_author_name
_audit_author_address
'Vladimir Arion'
;University of Vienna
Austria
;
_audit_update_record             
;
2023-05-10 deposited with the CCDC.	2023-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H29 Br N2 O4'
_chemical_formula_sum            'C25 H29 Br N2 O4'
_chemical_formula_weight         501.41

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0922(4)
_cell_length_b                   10.7884(5)
_cell_length_c                   13.2927(7)
_cell_angle_alpha                72.853(4)
_cell_angle_beta                 81.357(4)
_cell_angle_gamma                75.773(4)
_cell_volume                     1203.45(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    38204
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      30.56

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.633
_exptl_crystal_size_min          0.500
_exptl_absorpt_coefficient_mu    1.741
_shelx_estimated_absorpt_T_min   0.336
_shelx_estimated_absorpt_T_max   0.476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0240
_exptl_absorpt_correction_T_max  0.0358
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Primux 100 micro'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22693
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.319
_diffrn_reflns_theta_max         31.028
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             7151
_reflns_number_gt                4408
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)'
_computing_cell_refinement       'X-Area Recipe 1.36.0-0 (STOE, 2020)'
_computing_data_reduction        
'X-Area Integrate 1.78.3.0; X-Area LANA 1.83.8.0 (STOE, 2020)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0850P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7151
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1577
_refine_ls_wR_factor_gt          0.1358
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.32636(4) -0.09503(3) 0.71258(3) 0.04175(14) Uani 1 1 d . . . . .
N12 N 0.3266(2) 0.5416(2) 0.20849(17) 0.0233(5) Uani 1 1 d . . . . .
O25 O 0.5543(2) 0.5255(2) 0.09324(15) 0.0283(4) Uani 1 1 d . . . . .
O21 O 0.1819(2) 0.2979(2) 0.36714(14) 0.0269(4) Uani 1 1 d . . . . .
O1 O 0.5179(2) 0.4243(2) 0.39736(15) 0.0298(4) Uani 1 1 d . . . . .
O2 O 0.1222(2) 0.2257(2) 0.54288(15) 0.0316(5) Uani 1 1 d . . . . .
C15 C 0.0796(3) 0.7994(3) 0.0180(2) 0.0296(6) Uani 1 1 d . . . . .
H15 H 0.0666 0.8384 -0.0550 0.036 Uiso 1 1 calc R U . . .
C13 C 0.2159(3) 0.6422(3) 0.1566(2) 0.0237(5) Uani 1 1 d . . . . .
C14 C 0.2022(3) 0.6964(3) 0.0479(2) 0.0267(6) Uani 1 1 d . . . . .
H14 H 0.2742 0.6635 -0.0028 0.032 Uiso 1 1 calc R U . . .
C24 C 0.4446(3) 0.4581(3) 0.1568(2) 0.0274(6) Uani 1 1 d . . . . .
H24A H 0.4961 0.3820 0.2114 0.033 Uiso 1 1 calc R U . . .
H24B H 0.3968 0.4222 0.1125 0.033 Uiso 1 1 calc R U . . .
N9 N 0.3101(3) 0.3427(2) 0.48012(17) 0.0247(5) Uani 1 1 d . . . . .
C5 C 0.6282(3) 0.1225(3) 0.7443(2) 0.0323(7) Uani 1 1 d . . . . .
H5 H 0.6693 0.1967 0.7040 0.039 Uiso 1 1 calc R U . . .
C4 C 0.6709(4) 0.0595(3) 0.8455(2) 0.0334(7) Uani 1 1 d . . . . .
H4 H 0.7403 0.0906 0.8737 0.040 Uiso 1 1 calc R U . . .
C6 C 0.5263(3) 0.0801(3) 0.6992(2) 0.0271(6) Uani 1 1 d . . . . .
C10 C 0.3841(3) 0.4241(3) 0.3969(2) 0.0258(6) Uani 1 1 d . . . . .
C11 C 0.2871(3) 0.5205(3) 0.3164(2) 0.0245(5) Uani 1 1 d . . . . .
C8 C 0.3790(3) 0.2868(3) 0.5815(2) 0.0257(6) Uani 1 1 d . . . . .
H8A H 0.2971 0.2776 0.6398 0.031 Uiso 1 1 calc R U . . .
H8B H 0.4366 0.3489 0.5908 0.031 Uiso 1 1 calc R U . . .
C19 C 0.1542(3) 0.6068(3) 0.3333(2) 0.0265(6) Uani 1 1 d . . . . .
H19 H 0.1025 0.6118 0.4002 0.032 Uiso 1 1 calc R U . . .
C23C C 0.0804(4) 0.1077(3) 0.3709(3) 0.0427(8) Uani 1 1 d . . . . .
H23A H 0.1826 0.0689 0.3444 0.064 Uiso 1 1 calc R U . . .
H23B H 0.0043 0.0785 0.3435 0.064 Uiso 1 1 calc R U . . .
H23C H 0.0709 0.0786 0.4483 0.064 Uiso 1 1 calc R U . . .
C18 C 0.1073(3) 0.6877(3) 0.2337(2) 0.0251(6) Uani 1 1 d . . . . .
C23A C 0.0756(4) 0.3063(4) 0.2165(3) 0.0433(8) Uani 1 1 d . . . . .
H23D H 0.0692 0.4024 0.1960 0.065 Uiso 1 1 calc R U . . .
H23E H -0.0044 0.2869 0.1854 0.065 Uiso 1 1 calc R U . . .
H23F H 0.1755 0.2617 0.1911 0.065 Uiso 1 1 calc R U . . .
C22 C 0.0547(3) 0.2573(3) 0.3347(2) 0.0312(6) Uani 1 1 d . . . . .
C20 C 0.1939(3) 0.2848(3) 0.4680(2) 0.0251(6) Uani 1 1 d . . . . .
C7 C 0.4856(3) 0.1517(3) 0.5885(2) 0.0296(6) Uani 1 1 d . . . . .
H7A H 0.4360 0.0965 0.5623 0.036 Uiso 1 1 calc R U . . .
H7B H 0.5799 0.1640 0.5423 0.036 Uiso 1 1 calc R U . . .
C1 C 0.4682(3) -0.0285(3) 0.7635(2) 0.0276(6) Uani 1 1 d . . . . .
C26 C 0.6512(4) 0.5600(4) 0.1505(2) 0.0371(7) Uani 1 1 d . . . . .
H26A H 0.6848 0.4842 0.2115 0.045 Uiso 1 1 calc R U . . .
H26B H 0.5957 0.6366 0.1774 0.045 Uiso 1 1 calc R U . . .
C17 C -0.0143(3) 0.7940(3) 0.1992(2) 0.0296(6) Uani 1 1 d . . . . .
H17 H -0.0872 0.8280 0.2489 0.035 Uiso 1 1 calc R U . . .
C27 C 0.7856(3) 0.5948(3) 0.0781(2) 0.0354(7) Uani 1 1 d . . . . .
H27A H 0.7520 0.6735 0.0204 0.053 Uiso 1 1 calc R U . . .
H27B H 0.8365 0.5202 0.0487 0.053 Uiso 1 1 calc R U . . .
H27C H 0.8567 0.6135 0.1174 0.053 Uiso 1 1 calc R U . . .
C2 C 0.5099(3) -0.0928(3) 0.8643(2) 0.0316(6) Uani 1 1 d . . . . .
H2 H 0.4688 -0.1668 0.9053 0.038 Uiso 1 1 calc R U . . .
C16 C -0.0269(3) 0.8480(3) 0.0933(2) 0.0293(6) Uani 1 1 d . . . . .
H16 H -0.1093 0.9199 0.0700 0.035 Uiso 1 1 calc R U . . .
C3 C 0.6125(4) -0.0482(3) 0.9053(2) 0.0324(6) Uani 1 1 d . . . . .
H3 H 0.6425 -0.0921 0.9746 0.039 Uiso 1 1 calc R U . . .
C23B C -0.0980(4) 0.3261(4) 0.3783(3) 0.0500(10) Uani 1 1 d . . . . .
H23G H -0.1088 0.2910 0.4553 0.075 Uiso 1 1 calc R U . . .
H23H H -0.1805 0.3097 0.3476 0.075 Uiso 1 1 calc R U . . .
H23I H -0.1030 0.4218 0.3600 0.075 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 C1 1.909(3) . ?
N12 C13 1.377(3) . ?
N12 C11 1.390(3) . ?
N12 C24 1.451(3) . ?
O25 C24 1.407(3) . ?
O25 C26 1.422(3) . ?
O21 C20 1.324(3) . ?
O21 C22 1.492(3) . ?
O1 C10 1.218(3) . ?
O2 C20 1.208(3) . ?
C15 C14 1.378(4) . ?
C15 C16 1.408(4) . ?
C15 H15 0.9500 . ?
C13 C14 1.402(4) . ?
C13 C18 1.421(4) . ?
C14 H14 0.9500 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
N9 C10 1.393(3) . ?
N9 C20 1.402(4) . ?
N9 C8 1.470(3) . ?
C5 C4 1.382(4) . ?
C5 C6 1.400(4) . ?
C5 H5 0.9500 . ?
C4 C3 1.377(4) . ?
C4 H4 0.9500 . ?
C6 C1 1.400(4) . ?
C6 C7 1.501(4) . ?
C10 C11 1.477(4) . ?
C11 C19 1.366(4) . ?
C8 C7 1.525(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C19 C18 1.415(4) . ?
C19 H19 0.9500 . ?
C23C C22 1.510(4) . ?
C23C H23A 0.9800 . ?
C23C H23B 0.9800 . ?
C23C H23C 0.9800 . ?
C18 C17 1.403(4) . ?
C23A C22 1.501(4) . ?
C23A H23D 0.9800 . ?
C23A H23E 0.9800 . ?
C23A H23F 0.9800 . ?
C22 C23B 1.523(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C1 C2 1.376(4) . ?
C26 C27 1.490(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C17 C16 1.366(4) . ?
C17 H17 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C2 C3 1.388(4) . ?
C2 H2 0.9500 . ?
C16 H16 0.9500 . ?
C3 H3 0.9500 . ?
C23B H23G 0.9800 . ?
C23B H23H 0.9800 . ?
C23B H23I 0.9800 . ?

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
C13 N12 C11 107.9(2) . . ?
C13 N12 C24 124.1(2) . . ?
C11 N12 C24 127.0(2) . . ?
C24 O25 C26 114.4(2) . . ?
C20 O21 C22 120.7(2) . . ?
C14 C15 C16 121.5(3) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
N12 C13 C14 129.5(2) . . ?
N12 C13 C18 108.2(2) . . ?
C14 C13 C18 122.3(3) . . ?
C15 C14 C13 116.9(3) . . ?
C15 C14 H14 121.5 . . ?
C13 C14 H14 121.5 . . ?
O25 C24 N12 113.2(2) . . ?
O25 C24 H24A 108.9 . . ?
N12 C24 H24A 108.9 . . ?
O25 C24 H24B 108.9 . . ?
N12 C24 H24B 108.9 . . ?
H24A C24 H24B 107.8 . . ?
C10 N9 C20 123.9(2) . . ?
C10 N9 C8 118.8(2) . . ?
C20 N9 C8 115.6(2) . . ?
C4 C5 C6 122.0(3) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C5 C6 C1 116.0(3) . . ?
C5 C6 C7 119.6(3) . . ?
C1 C6 C7 124.4(3) . . ?
O1 C10 N9 121.1(3) . . ?
O1 C10 C11 122.3(3) . . ?
N9 C10 C11 116.1(2) . . ?
C19 C11 N12 109.6(2) . . ?
C19 C11 C10 127.3(2) . . ?
N12 C11 C10 123.0(2) . . ?
N9 C8 C7 112.3(2) . . ?
N9 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
N9 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C11 C19 C18 107.8(2) . . ?
C11 C19 H19 126.1 . . ?
C18 C19 H19 126.1 . . ?
C22 C23C H23A 109.5 . . ?
C22 C23C H23B 109.5 . . ?
H23A C23C H23B 109.5 . . ?
C22 C23C H23C 109.5 . . ?
H23A C23C H23C 109.5 . . ?
H23B C23C H23C 109.5 . . ?
C17 C18 C19 135.1(3) . . ?
C17 C18 C13 118.5(3) . . ?
C19 C18 C13 106.4(2) . . ?
C22 C23A H23D 109.5 . . ?
C22 C23A H23E 109.5 . . ?
H23D C23A H23E 109.5 . . ?
C22 C23A H23F 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
O21 C22 C23A 101.7(2) . . ?
O21 C22 C23C 108.3(2) . . ?
C23A C22 C23C 111.5(3) . . ?
O21 C22 C23B 110.3(2) . . ?
C23A C22 C23B 111.4(3) . . ?
C23C C22 C23B 113.0(3) . . ?
O2 C20 O21 126.5(3) . . ?
O2 C20 N9 122.0(2) . . ?
O21 C20 N9 111.5(2) . . ?
C6 C7 C8 112.3(2) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C2 C1 C6 122.8(3) . . ?
C2 C1 Br1 116.9(2) . . ?
C6 C1 Br1 120.3(2) . . ?
O25 C26 C27 108.4(2) . . ?
O25 C26 H26A 110.0 . . ?
C27 C26 H26A 110.0 . . ?
O25 C26 H26B 110.0 . . ?
C27 C26 H26B 110.0 . . ?
H26A C26 H26B 108.4 . . ?
C16 C17 C18 119.2(3) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C1 C2 C3 119.2(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C17 C16 C15 121.5(3) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C22 C23B H23G 109.5 . . ?
C22 C23B H23H 109.5 . . ?
H23G C23B H23H 109.5 . . ?
C22 C23B H23I 109.5 . . ?
H23G C23B H23I 109.5 . . ?
H23H C23B H23I 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
C11 N12 C13 C14 -177.8(3) . . . . ?
C24 N12 C13 C14 -8.8(4) . . . . ?
C11 N12 C13 C18 1.8(3) . . . . ?
C24 N12 C13 C18 170.8(2) . . . . ?
C16 C15 C14 C13 0.1(4) . . . . ?
N12 C13 C14 C15 -178.8(3) . . . . ?
C18 C13 C14 C15 1.7(4) . . . . ?
C26 O25 C24 N12 70.0(3) . . . . ?
C13 N12 C24 O25 70.7(3) . . . . ?
C11 N12 C24 O25 -122.4(3) . . . . ?
C6 C5 C4 C3 -0.1(5) . . . . ?
C4 C5 C6 C1 1.0(5) . . . . ?
C4 C5 C6 C7 -179.4(3) . . . . ?
C20 N9 C10 O1 -146.6(3) . . . . ?
C8 N9 C10 O1 17.8(4) . . . . ?
C20 N9 C10 C11 40.7(4) . . . . ?
C8 N9 C10 C11 -154.9(2) . . . . ?
C13 N12 C11 C19 -0.6(3) . . . . ?
C24 N12 C11 C19 -169.2(3) . . . . ?
C13 N12 C11 C10 -176.8(2) . . . . ?
C24 N12 C11 C10 14.6(4) . . . . ?
O1 C10 C11 C19 -122.9(3) . . . . ?
N9 C10 C11 C19 49.7(4) . . . . ?
O1 C10 C11 N12 52.6(4) . . . . ?
N9 C10 C11 N12 -134.9(3) . . . . ?
C10 N9 C8 C7 -90.9(3) . . . . ?
C20 N9 C8 C7 74.8(3) . . . . ?
N12 C11 C19 C18 -0.8(3) . . . . ?
C10 C11 C19 C18 175.1(3) . . . . ?
C11 C19 C18 C17 -178.2(3) . . . . ?
C11 C19 C18 C13 1.9(3) . . . . ?
N12 C13 C18 C17 177.8(2) . . . . ?
C14 C13 C18 C17 -2.5(4) . . . . ?
N12 C13 C18 C19 -2.3(3) . . . . ?
C14 C13 C18 C19 177.3(3) . . . . ?
C20 O21 C22 C23A 172.8(2) . . . . ?
C20 O21 C22 C23C -69.8(3) . . . . ?
C20 O21 C22 C23B 54.4(3) . . . . ?
C22 O21 C20 O2 10.5(4) . . . . ?
C22 O21 C20 N9 -173.1(2) . . . . ?
C10 N9 C20 O2 -172.5(3) . . . . ?
C8 N9 C20 O2 22.6(4) . . . . ?
C10 N9 C20 O21 10.9(4) . . . . ?
C8 N9 C20 O21 -154.0(2) . . . . ?
C5 C6 C7 C8 -73.7(3) . . . . ?
C1 C6 C7 C8 105.8(3) . . . . ?
N9 C8 C7 C6 -166.3(2) . . . . ?
C5 C6 C1 C2 -1.4(4) . . . . ?
C7 C6 C1 C2 179.1(3) . . . . ?
C5 C6 C1 Br1 179.3(2) . . . . ?
C7 C6 C1 Br1 -0.3(4) . . . . ?
C24 O25 C26 C27 164.3(3) . . . . ?
C19 C18 C17 C16 -178.2(3) . . . . ?
C13 C18 C17 C16 1.6(4) . . . . ?
C6 C1 C2 C3 0.7(5) . . . . ?
Br1 C1 C2 C3 -179.9(2) . . . . ?
C18 C17 C16 C15 0.0(4) . . . . ?
C14 C15 C16 C17 -0.9(4) . . . . ?
C5 C4 C3 C2 -0.6(5) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C24 H24A Br1 0.99 3.07 3.969(3) 152.3 2_656
C24 H24B O25 0.99 2.62 3.275(3) 124.1 2_665
C8 H8B O1 0.99 2.63 3.564(4) 157.1 2_666
C19 H19 O2 0.95 2.53 3.251(3) 133.2 2_566
C23C H23C O2 0.98 2.46 3.034(4) 117.4 .
C7 H7A Br1 0.99 2.69 3.238(3) 115.3 .
C23B H23G O2 0.98 2.41 2.970(4) 116.1 .

_refine_diff_density_max         0.638
_refine_diff_density_min         -1.502
_refine_diff_density_rms         0.103

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_chwi665
_database_code_depnum_ccdc_archive 'CCDC 2261961'
loop_
_audit_author_name
_audit_author_address
'Vladimir Arion'
;University of Vienna
Austria
;
_audit_update_record             
;
2023-05-10 deposited with the CCDC.	2023-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 Cl2 Cu N5, 2(C3 H7 N O)'
_chemical_formula_sum            'C30 H35 Cl2 Cu N7 O2'
_chemical_formula_weight         660.09

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8729(2)
_cell_length_b                   9.9230(2)
_cell_length_c                   16.4367(4)
_cell_angle_alpha                77.4544(10)
_cell_angle_beta                 76.6520(12)
_cell_angle_gamma                85.2866(10)
_cell_volume                     1528.50(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9954
_cell_measurement_theta_min      2.602
_cell_measurement_theta_max      29.709

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             686
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    0.930
_shelx_estimated_absorpt_T_min   0.703
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4875
_exptl_absorpt_correction_T_max  0.5642
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37246
_diffrn_reflns_av_unetI/netI     0.0733
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.104
_diffrn_reflns_theta_max         30.087
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             8880
_reflns_number_gt                6201
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0296P)²+0.7176P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8880
_refine_ls_number_parameters     384
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.0945
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cu Cu 0.32205(2) 0.17244(2) 0.53583(2) 0.01658(7) Uani 1 1 d . . . . .
Cl1 Cl 0.13704(5) 0.03901(5) 0.57783(3) 0.02514(12) Uani 1 1 d . . . . .
Cl2 Cl 0.25736(5) 0.35001(5) 0.62597(3) 0.02171(11) Uani 1 1 d . . . . .
C1 C 0.2983(2) 0.3665(2) 0.13852(13) 0.0233(4) Uani 1 1 d . . . . .
H1 H 0.3834 0.3932 0.0995 0.028 Uiso 1 1 calc R U . . .
C2 C 0.2125(2) 0.2810(2) 0.11912(14) 0.0273(5) Uani 1 1 d . . . . .
H2 H 0.2388 0.2490 0.0670 0.033 Uiso 1 1 calc R U . . .
C3 C 0.0876(2) 0.2416(2) 0.17564(15) 0.0303(5) Uani 1 1 d . . . . .
H3 H 0.0281 0.1828 0.1624 0.036 Uiso 1 1 calc R U . . .
C4 C 0.0507(2) 0.2884(2) 0.25120(14) 0.0265(5) Uani 1 1 d . . . . .
H4 H -0.0340 0.2597 0.2901 0.032 Uiso 1 1 calc R U . . .
C4A C 0.1340(2) 0.3765(2) 0.27182(13) 0.0211(4) Uani 1 1 d . . . . .
C5 C 0.0877(2) 0.4296(2) 0.35379(13) 0.0232(4) Uani 1 1 d . . . . .
H5A H -0.0148 0.4443 0.3658 0.028 Uiso 1 1 calc R U . . .
H5B H 0.1296 0.5200 0.3460 0.028 Uiso 1 1 calc R U . . .
C6 C 0.1283(2) 0.3316(2) 0.43038(13) 0.0238(5) Uani 1 1 d . . . . .
H6A H 0.0815 0.3668 0.4821 0.029 Uiso 1 1 calc R U . . .
H6B H 0.0888 0.2409 0.4354 0.029 Uiso 1 1 calc R U . . .
N7 N 0.27561(17) 0.30729(17) 0.43261(10) 0.0183(3) Uani 1 1 d . . . . .
C8 C 0.3796(2) 0.3809(2) 0.38800(12) 0.0170(4) Uani 1 1 d . . . . .
C8A C 0.3924(2) 0.49515(19) 0.31173(12) 0.0171(4) Uani 1 1 d . . . . .
N9 N 0.47933(17) 0.60154(16) 0.30535(10) 0.0190(3) Uani 1 1 d D . . . .
H9 H 0.5160 0.6162 0.3465 0.023 Uiso 1 1 calc DR U . . .
C9A C 0.4986(2) 0.6802(2) 0.22399(12) 0.0187(4) Uani 1 1 d . . . . .
C10 C 0.5776(2) 0.7978(2) 0.18813(14) 0.0240(4) Uani 1 1 d . . . . .
H10 H 0.6283 0.8350 0.2203 0.029 Uiso 1 1 calc R U . . .
C11 C 0.5785(2) 0.8576(2) 0.10378(14) 0.0285(5) Uani 1 1 d . . . . .
H11 H 0.6318 0.9371 0.0771 0.034 Uiso 1 1 calc R U . . .
C12 C 0.5022(2) 0.8033(2) 0.05675(14) 0.0282(5) Uani 1 1 d . . . . .
H12 H 0.5049 0.8472 -0.0010 0.034 Uiso 1 1 calc R U . . .
C13 C 0.4235(2) 0.6880(2) 0.09223(13) 0.0237(4) Uani 1 1 d . . . . .
H13 H 0.3713 0.6530 0.0600 0.028 Uiso 1 1 calc R U . . .
C13A C 0.4226(2) 0.6233(2) 0.17799(12) 0.0189(4) Uani 1 1 d . . . . .
C13B C 0.3538(2) 0.5049(2) 0.23493(12) 0.0178(4) Uani 1 1 d . . . . .
C13C C 0.2615(2) 0.4147(2) 0.21515(12) 0.0190(4) Uani 1 1 d . . . . .
N14 N 0.50626(17) 0.35541(16) 0.41208(10) 0.0175(3) Uani 1 1 d D . . . .
H14 H 0.5808 0.4029 0.3853 0.021 Uiso 1 1 calc DR U . . .
N15 N 0.50485(17) 0.24971(16) 0.48131(10) 0.0171(3) Uani 1 1 d . . . . .
C16 C 0.6104(2) 0.2136(2) 0.51456(12) 0.0177(4) Uani 1 1 d . . . . .
C17 C 0.5811(2) 0.09591(19) 0.58846(12) 0.0177(4) Uani 1 1 d . . . . .
N18 N 0.44819(17) 0.05188(16) 0.60836(10) 0.0170(3) Uani 1 1 d . . . . .
C19 C 0.4121(2) -0.0539(2) 0.67407(13) 0.0210(4) Uani 1 1 d . . . . .
H19 H 0.3200 -0.0860 0.6874 0.025 Uiso 1 1 calc R U . . .
C20 C 0.5047(2) -0.1182(2) 0.72333(13) 0.0249(5) Uani 1 1 d . . . . .
H20 H 0.4759 -0.1924 0.7702 0.030 Uiso 1 1 calc R U . . .
C21 C 0.6391(2) -0.0732(2) 0.70356(14) 0.0258(5) Uani 1 1 d . . . . .
H21 H 0.7040 -0.1158 0.7367 0.031 Uiso 1 1 calc R U . . .
C22 C 0.6786(2) 0.0353(2) 0.63448(13) 0.0223(4) Uani 1 1 d . . . . .
H22 H 0.7710 0.0671 0.6192 0.027 Uiso 1 1 calc R U . . .
C23 C 0.7474(2) 0.2807(2) 0.48620(14) 0.0249(5) Uani 1 1 d . . . . .
H23A H 0.8149 0.2232 0.4537 0.037 Uiso 1 1 calc R U . . .
H23B H 0.7803 0.2913 0.5363 0.037 Uiso 1 1 calc R U . . .
H23C H 0.7373 0.3717 0.4499 0.037 Uiso 1 1 calc R U . . .
O1 O 1.15590(18) -0.02836(17) 0.86303(11) 0.0378(4) Uani 1 1 d . . . . .
C24 C 1.0998(2) 0.0552(2) 0.81350(15) 0.0287(5) Uani 1 1 d . . . . .
H24 H 1.1531 0.0855 0.7573 0.034 Uiso 1 1 calc R U . . .
N24 N 0.9702(2) 0.10733(19) 0.83174(12) 0.0291(4) Uani 1 1 d . . . . .
C25 C 0.9118(3) 0.2038(3) 0.76768(16) 0.0403(6) Uani 1 1 d . . . . .
H25A H 0.8285 0.1653 0.7599 0.061 Uiso 1 1 calc R U . . .
H25B H 0.9809 0.2197 0.7134 0.061 Uiso 1 1 calc R U . . .
H25C H 0.8867 0.2915 0.7865 0.061 Uiso 1 1 calc R U . . .
C26 C 0.8810(3) 0.0682(3) 0.91636(16) 0.0423(7) Uani 1 1 d . . . . .
H26A H 0.8678 0.1466 0.9451 0.063 Uiso 1 1 calc R U . . .
H26B H 0.9246 -0.0101 0.9498 0.063 Uiso 1 1 calc R U . . .
H26C H 0.7904 0.0417 0.9111 0.063 Uiso 1 1 calc R U . . .
O2 O 0.29909(16) 0.63962(16) 0.73525(9) 0.0279(4) Uani 1 1 d . . . . .
C27 C 0.2257(2) 0.5424(2) 0.77712(13) 0.0233(4) Uani 1 1 d . . . . .
H27 H 0.1938 0.4847 0.7467 0.028 Uiso 1 1 calc R U . . .
N27 N 0.18862(19) 0.51326(19) 0.86149(11) 0.0252(4) Uani 1 1 d . . . . .
C28 C 0.2368(3) 0.5959(3) 0.91127(16) 0.0493(8) Uani 1 1 d . . . . .
H28A H 0.3361 0.6129 0.8882 0.074 Uiso 1 1 calc R U . . .
H28B H 0.2229 0.5464 0.9709 0.074 Uiso 1 1 calc R U . . .
H28C H 0.1841 0.6843 0.9083 0.074 Uiso 1 1 calc R U . . .
C29 C 0.0944(3) 0.4018(3) 0.90409(17) 0.0458(7) Uani 1 1 d . . . . .
H29A H 0.0036 0.4405 0.9289 0.069 Uiso 1 1 calc R U . . .
H29B H 0.1329 0.3413 0.9495 0.069 Uiso 1 1 calc R U . . .
H29C H 0.0831 0.3484 0.8626 0.069 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
Cu N15 1.9571(16) . ?
Cu N7 2.0375(17) . ?
Cu N18 2.0554(17) . ?
Cu Cl1 2.2325(5) . ?
Cu Cl2 2.4940(5) . ?
C1 C2 1.378(3) . ?
C1 C13C 1.403(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C4A 1.390(3) . ?
C4 H4 0.9500 . ?
C4A C13C 1.407(3) . ?
C4A C5 1.512(3) . ?
C5 C6 1.526(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N7 1.462(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
N7 C8 1.291(2) . ?
C8 N14 1.385(3) . ?
C8 C8A 1.485(3) . ?
C8A C13B 1.382(3) . ?
C8A N9 1.386(3) . ?
N9 C9A 1.374(2) . ?
N9 H9 0.8800 . ?
C9A C10 1.399(3) . ?
C9A C13A 1.404(3) . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.404(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(3) . ?
C12 H12 0.9500 . ?
C13 C13A 1.415(3) . ?
C13 H13 0.9500 . ?
C13A C13B 1.441(3) . ?
C13B C13C 1.461(3) . ?
N14 N15 1.368(2) . ?
N14 H14 0.8800 . ?
N15 C16 1.277(3) . ?
C16 C17 1.483(3) . ?
C16 C23 1.488(3) . ?
C17 N18 1.362(3) . ?
C17 C22 1.379(3) . ?
N18 C19 1.336(2) . ?
C19 C20 1.385(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.379(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O1 C24 1.223(3) . ?
C24 N24 1.333(3) . ?
C24 H24 0.9500 . ?
N24 C25 1.452(3) . ?
N24 C26 1.455(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
O2 C27 1.235(3) . ?
C27 N27 1.323(3) . ?
C27 H27 0.9500 . ?
N27 C28 1.451(3) . ?
N27 C29 1.453(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?

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
N15 Cu N7 79.40(7) . . ?
N15 Cu N18 78.04(7) . . ?
N7 Cu N18 156.45(6) . . ?
N15 Cu Cl1 164.17(5) . . ?
N7 Cu Cl1 101.74(5) . . ?
N18 Cu Cl1 98.15(5) . . ?
N15 Cu Cl2 93.00(5) . . ?
N7 Cu Cl2 91.41(5) . . ?
N18 Cu Cl2 96.42(5) . . ?
Cl1 Cu Cl2 102.73(2) . . ?
C2 C1 C13C 120.89(19) . . ?
C2 C1 H1 119.6 . . ?
C13C C1 H1 119.6 . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C4A 121.8(2) . . ?
C3 C4 H4 119.1 . . ?
C4A C4 H4 119.1 . . ?
C4 C4A C13C 118.71(19) . . ?
C4 C4A C5 120.24(18) . . ?
C13C C4A C5 121.05(19) . . ?
C4A C5 C6 113.14(17) . . ?
C4A C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
C4A C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
N7 C6 C5 119.29(16) . . ?
N7 C6 H6A 107.5 . . ?
C5 C6 H6A 107.5 . . ?
N7 C6 H6B 107.5 . . ?
C5 C6 H6B 107.5 . . ?
H6A C6 H6B 107.0 . . ?
C8 N7 C6 128.04(17) . . ?
C8 N7 Cu 113.03(14) . . ?
C6 N7 Cu 117.09(12) . . ?
N7 C8 N14 118.30(17) . . ?
N7 C8 C8A 131.96(19) . . ?
N14 C8 C8A 109.74(16) . . ?
C13B C8A N9 109.86(16) . . ?
C13B C8A C8 130.95(18) . . ?
N9 C8A C8 117.90(18) . . ?
C9A N9 C8A 108.52(17) . . ?
C9A N9 H9 125.7 . . ?
C8A N9 H9 125.7 . . ?
N9 C9A C10 129.0(2) . . ?
N9 C9A C13A 108.28(17) . . ?
C10 C9A C13A 122.69(19) . . ?
C11 C10 C9A 117.0(2) . . ?
C11 C10 H10 121.5 . . ?
C9A C10 H10 121.5 . . ?
C10 C11 C12 121.4(2) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C13 C12 C11 121.7(2) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C13A 118.2(2) . . ?
C12 C13 H13 120.9 . . ?
C13A C13 H13 120.9 . . ?
C9A C13A C13 119.10(18) . . ?
C9A C13A C13B 107.37(17) . . ?
C13 C13A C13B 133.5(2) . . ?
C8A C13B C13A 105.97(18) . . ?
C8A C13B C13C 127.31(17) . . ?
C13A C13B C13C 126.72(18) . . ?
C1 C13C C4A 119.10(19) . . ?
C1 C13C C13B 120.24(17) . . ?
C4A C13C C13B 120.65(18) . . ?
N15 N14 C8 113.81(15) . . ?
N15 N14 H14 123.1 . . ?
C8 N14 H14 123.1 . . ?
C16 N15 N14 123.07(17) . . ?
C16 N15 Cu 121.39(13) . . ?
N14 N15 Cu 115.08(13) . . ?
N15 C16 C17 112.11(17) . . ?
N15 C16 C23 125.66(18) . . ?
C17 C16 C23 122.21(18) . . ?
N18 C17 C22 121.92(18) . . ?
N18 C17 C16 114.42(17) . . ?
C22 C17 C16 123.66(18) . . ?
C19 N18 C17 118.71(18) . . ?
C19 N18 Cu 127.89(14) . . ?
C17 N18 Cu 113.20(13) . . ?
N18 C19 C20 122.2(2) . . ?
N18 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C21 C20 C19 119.18(19) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C20 C21 C22 119.2(2) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C17 C22 C21 118.8(2) . . ?
C17 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
C16 C23 H23A 109.5 . . ?
C16 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C16 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O1 C24 N24 125.5(2) . . ?
O1 C24 H24 117.2 . . ?
N24 C24 H24 117.2 . . ?
C24 N24 C25 121.35(19) . . ?
C24 N24 C26 121.2(2) . . ?
C25 N24 C26 117.42(19) . . ?
N24 C25 H25A 109.5 . . ?
N24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N24 C26 H26A 109.5 . . ?
N24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O2 C27 N27 124.3(2) . . ?
O2 C27 H27 117.9 . . ?
N27 C27 H27 117.9 . . ?
C27 N27 C28 120.24(19) . . ?
C27 N27 C29 119.7(2) . . ?
C28 N27 C29 119.99(19) . . ?
N27 C28 H28A 109.5 . . ?
N27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N27 C29 H29A 109.5 . . ?
N27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
C13C C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C4A 1.2(3) . . . . ?
C3 C4 C4A C13C -2.2(3) . . . . ?
C3 C4 C4A C5 177.91(19) . . . . ?
C4 C4A C5 C6 86.2(2) . . . . ?
C13C C4A C5 C6 -93.7(2) . . . . ?
C4A C5 C6 N7 66.3(3) . . . . ?
C5 C6 N7 C8 17.7(3) . . . . ?
C5 C6 N7 Cu -178.89(15) . . . . ?
C6 N7 C8 N14 167.08(18) . . . . ?
Cu N7 C8 N14 3.2(2) . . . . ?
C6 N7 C8 C8A -12.4(4) . . . . ?
Cu N7 C8 C8A -176.28(17) . . . . ?
N7 C8 C8A C13B -50.2(3) . . . . ?
N14 C8 C8A C13B 130.3(2) . . . . ?
N7 C8 C8A N9 144.2(2) . . . . ?
N14 C8 C8A N9 -35.2(2) . . . . ?
C13B C8A N9 C9A -0.5(2) . . . . ?
C8 C8A N9 C9A 167.91(16) . . . . ?
C8A N9 C9A C10 179.9(2) . . . . ?
C8A N9 C9A C13A 0.1(2) . . . . ?
N9 C9A C10 C11 -179.80(19) . . . . ?
C13A C9A C10 C11 -0.1(3) . . . . ?
C9A C10 C11 C12 0.7(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C13A -0.9(3) . . . . ?
N9 C9A C13A C13 178.78(17) . . . . ?
C10 C9A C13A C13 -1.0(3) . . . . ?
N9 C9A C13A C13B 0.3(2) . . . . ?
C10 C9A C13A C13B -179.48(18) . . . . ?
C12 C13 C13A C9A 1.4(3) . . . . ?
C12 C13 C13A C13B 179.4(2) . . . . ?
N9 C8A C13B C13A 0.7(2) . . . . ?
C8 C8A C13B C13A -165.73(19) . . . . ?
N9 C8A C13B C13C -178.96(18) . . . . ?
C8 C8A C13B C13C 14.6(3) . . . . ?
C9A C13A C13B C8A -0.6(2) . . . . ?
C13 C13A C13B C8A -178.8(2) . . . . ?
C9A C13A C13B C13C 179.05(18) . . . . ?
C13 C13A C13B C13C 0.9(4) . . . . ?
C2 C1 C13C C4A -1.1(3) . . . . ?
C2 C1 C13C C13B 179.80(19) . . . . ?
C4 C4A C13C C1 2.1(3) . . . . ?
C5 C4A C13C C1 -178.01(18) . . . . ?
C4 C4A C13C C13B -178.81(19) . . . . ?
C5 C4A C13C C13B 1.1(3) . . . . ?
C8A C13B C13C C1 -134.9(2) . . . . ?
C13A C13B C13C C1 45.5(3) . . . . ?
C8A C13B C13C C4A 46.0(3) . . . . ?
C13A C13B C13C C4A -133.6(2) . . . . ?
N7 C8 N14 N15 1.4(3) . . . . ?
C8A C8 N14 N15 -179.00(15) . . . . ?
C8 N14 N15 C16 -177.86(18) . . . . ?
C8 N14 N15 Cu -5.6(2) . . . . ?
N14 N15 C16 C17 -179.69(15) . . . . ?
Cu N15 C16 C17 8.5(2) . . . . ?
N14 N15 C16 C23 1.8(3) . . . . ?
Cu N15 C16 C23 -169.98(15) . . . . ?
N15 C16 C17 N18 -1.9(2) . . . . ?
C23 C16 C17 N18 176.66(18) . . . . ?
N15 C16 C17 C22 178.58(19) . . . . ?
C23 C16 C17 C22 -2.9(3) . . . . ?
C22 C17 N18 C19 -0.5(3) . . . . ?
C16 C17 N18 C19 179.94(16) . . . . ?
C22 C17 N18 Cu 174.79(15) . . . . ?
C16 C17 N18 Cu -4.8(2) . . . . ?
C17 N18 C19 C20 1.2(3) . . . . ?
Cu N18 C19 C20 -173.34(15) . . . . ?
N18 C19 C20 C21 -0.8(3) . . . . ?
C19 C20 C21 C22 -0.2(3) . . . . ?
N18 C17 C22 C21 -0.5(3) . . . . ?
C16 C17 C22 C21 179.00(18) . . . . ?
C20 C21 C22 C17 0.9(3) . . . . ?
O1 C24 N24 C25 -178.5(2) . . . . ?
O1 C24 N24 C26 0.6(4) . . . . ?
O2 C27 N27 C28 -1.4(3) . . . . ?
O2 C27 N27 C29 176.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6B Cl1 0.99 2.84 3.363(2) 114.0 .
N9 H9 Cl2 0.88 2.45 3.1718(18) 140.2 2_666
N14 H14 Cl2 0.88 2.99 3.7463(17) 145.9 2_666
N14 H14 O2 0.88 2.17 2.716(2) 119.7 2_666
C19 H19 Cl1 0.95 2.87 3.416(2) 118.0 .
C23 H23A Cl1 0.98 2.74 3.574(2) 142.7 2_656
C23 H23C Cl2 0.98 2.77 3.729(2) 165.8 2_666
C27 H27 Cl2 0.95 2.56 3.394(2) 146.4 .

_refine_diff_density_max         0.475
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.079

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_chwi360
_database_code_depnum_ccdc_archive 'CCDC 2261960'
loop_
_audit_author_name
_audit_author_address
'Vladimir Arion'
;University of Vienna
Austria
;
_audit_update_record             
;
2023-05-10 deposited with the CCDC.	2023-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 N2 S, 0.5(C H4 O)'
_chemical_formula_sum            'C17.50 H16 N2 O0.50 S'
_chemical_formula_weight         294.38

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1130(2)
_cell_length_b                   10.6532(2)
_cell_length_c                   16.7093(5)
_cell_angle_alpha                108.2046(11)
_cell_angle_beta                 100.2398(10)
_cell_angle_gamma                92.5769(7)
_cell_volume                     1507.65(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9918
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      44.23

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             620
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.358
_exptl_crystal_size_mid          0.309
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.212
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6960
_exptl_absorpt_correction_T_max  0.7492
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36358
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.284
_diffrn_reflns_theta_max         35.629
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             13634
_reflns_number_gt                11272
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT v8.38A'
_computing_data_reduction        'SAINT v8.38A'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0385P)²+0.6907P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13634
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.34068(11) -0.06690(10) 0.10988(6) 0.01709(16) Uani 1 1 d . . . . .
H1 H 0.3492 0.0193 0.1046 0.021 Uiso 1 1 calc R U . . .
C2 C 0.40034(12) -0.17010(12) 0.05533(7) 0.0231(2) Uani 1 1 d . . . . .
H2 H 0.4502 -0.1542 0.0135 0.028 Uiso 1 1 calc R U . . .
C3 C 0.38658(14) -0.29663(12) 0.06236(7) 0.0270(2) Uani 1 1 d . . . . .
H3 H 0.4274 -0.3674 0.0255 0.032 Uiso 1 1 calc R U . . .
C4 C 0.31316(13) -0.31925(11) 0.12329(7) 0.0237(2) Uani 1 1 d . . . . .
H4 H 0.3033 -0.4061 0.1274 0.028 Uiso 1 1 calc R U . . .
C4A C 0.25328(10) -0.21645(9) 0.17890(6) 0.01588(16) Uani 1 1 d . . . . .
C5 C 0.17596(11) -0.24422(10) 0.24509(7) 0.01824(17) Uani 1 1 d . . . . .
H5A H 0.1283 -0.3371 0.2224 0.022 Uiso 1 1 calc R U . . .
H5B H 0.0957 -0.1850 0.2551 0.022 Uiso 1 1 calc R U . . .
C6 C 0.28290(11) -0.22350(10) 0.33009(7) 0.01788(17) Uani 1 1 d . . . . .
H6A H 0.2270 -0.2544 0.3673 0.021 Uiso 1 1 calc R U . . .
H6B H 0.3632 -0.2822 0.3184 0.021 Uiso 1 1 calc R U . . .
N7 N 0.35529(9) -0.08801(8) 0.37967(5) 0.01594(14) Uani 1 1 d . . . . .
H7 H 0.4405 -0.0877 0.4141 0.019 Uiso 1 1 calc R U . . .
C8 C 0.32113(10) 0.03337(9) 0.38407(6) 0.01391(15) Uani 1 1 d . . . . .
S1 S 0.40902(3) 0.16643(2) 0.46862(2) 0.01800(5) Uani 1 1 d . . . . .
C8A C 0.21390(10) 0.06123(9) 0.31645(6) 0.01287(14) Uani 1 1 d . . . . .
N9 N 0.12696(9) 0.16438(8) 0.34052(5) 0.01647(14) Uani 1 1 d . . . . .
H9 H 0.1192 0.2072 0.3937 0.020 Uiso 1 1 calc R U . . .
C9A C 0.05489(10) 0.18956(9) 0.26895(6) 0.01525(15) Uani 1 1 d . . . . .
C10 C -0.05065(12) 0.27875(11) 0.26113(7) 0.02143(19) Uani 1 1 d . . . . .
H10 H -0.0821 0.3354 0.3099 0.026 Uiso 1 1 calc R U . . .
C11 C -0.10705(13) 0.28055(11) 0.17890(7) 0.0239(2) Uani 1 1 d . . . . .
H11 H -0.1800 0.3389 0.1712 0.029 Uiso 1 1 calc R U . . .
C12 C -0.05905(12) 0.19799(11) 0.10627(7) 0.02035(18) Uani 1 1 d . . . . .
H12 H -0.0982 0.2035 0.0510 0.024 Uiso 1 1 calc R U . . .
C13 C 0.04414(10) 0.10923(10) 0.11448(6) 0.01543(15) Uani 1 1 d . . . . .
H13 H 0.0759 0.0536 0.0655 0.019 Uiso 1 1 calc R U . . .
C13A C 0.10099(10) 0.10309(9) 0.19693(6) 0.01252(14) Uani 1 1 d . . . . .
C13B C 0.20007(10) 0.01965(8) 0.22760(5) 0.01174(14) Uani 1 1 d . . . . .
C13C C 0.26812(10) -0.08866(9) 0.17250(6) 0.01339(14) Uani 1 1 d . . . . .
C14 C -0.20857(12) 0.61083(10) 0.12547(6) 0.01909(17) Uani 1 1 d . . . . .
H14 H -0.2073 0.5202 0.1221 0.023 Uiso 1 1 calc R U . . .
C15 C -0.17021(13) 0.64946(12) 0.05916(7) 0.0249(2) Uani 1 1 d . . . . .
H15 H -0.1435 0.5861 0.0113 0.030 Uiso 1 1 calc R U . . .
C16 C -0.17138(14) 0.78197(13) 0.06364(7) 0.0265(2) Uani 1 1 d . . . . .
H16 H -0.1448 0.8101 0.0190 0.032 Uiso 1 1 calc R U . . .
C17 C -0.21154(12) 0.87224(11) 0.13371(7) 0.02189(19) Uani 1 1 d . . . . .
H17 H -0.2120 0.9625 0.1362 0.026 Uiso 1 1 calc R U . . .
C17A C -0.25167(10) 0.83582(10) 0.20140(6) 0.01638(16) Uani 1 1 d . . . . .
C18 C -0.30179(12) 0.94688(10) 0.26966(7) 0.02007(18) Uani 1 1 d . . . . .
H18A H -0.2398 1.0302 0.2775 0.024 Uiso 1 1 calc R U . . .
H18B H -0.4067 0.9580 0.2471 0.024 Uiso 1 1 calc R U . . .
C19 C -0.29462(11) 0.93199(9) 0.35735(6) 0.01718(16) Uani 1 1 d . . . . .
H19A H -0.3233 1.0140 0.3962 0.021 Uiso 1 1 calc R U . . .
H19B H -0.3688 0.8575 0.3520 0.021 Uiso 1 1 calc R U . . .
N20 N -0.14601(9) 0.90716(8) 0.39621(5) 0.01571(14) Uani 1 1 d . . . . .
H20 H -0.0743 0.9737 0.4151 0.019 Uiso 1 1 calc R U . . .
C21 C -0.11180(10) 0.79181(9) 0.40501(6) 0.01326(14) Uani 1 1 d . . . . .
S2 S 0.03660(3) 0.78106(2) 0.47892(2) 0.01507(5) Uani 1 1 d . . . . .
C21A C -0.21100(10) 0.67426(9) 0.34922(6) 0.01309(14) Uani 1 1 d . . . . .
N22 N -0.24865(9) 0.57535(8) 0.38135(5) 0.01428(13) Uani 1 1 d . . . . .
H22 H -0.2140 0.5736 0.4336 0.017 Uiso 1 1 calc R U . . .
C22A C -0.34883(10) 0.48039(9) 0.31845(6) 0.01376(15) Uani 1 1 d . . . . .
C23 C -0.42192(11) 0.36399(10) 0.32216(7) 0.01817(17) Uani 1 1 d . . . . .
H23 H -0.4044 0.3400 0.3730 0.022 Uiso 1 1 calc R U . . .
C24 C -0.52040(12) 0.28596(10) 0.24863(7) 0.02152(19) Uani 1 1 d . . . . .
H24 H -0.5722 0.2068 0.2490 0.026 Uiso 1 1 calc R U . . .
C25 C -0.54590(12) 0.32105(10) 0.17290(7) 0.02002(18) Uani 1 1 d . . . . .
H25 H -0.6150 0.2654 0.1236 0.024 Uiso 1 1 calc R U . . .
C26 C -0.47239(11) 0.43481(9) 0.16896(6) 0.01583(15) Uani 1 1 d . . . . .
H26 H -0.4891 0.4568 0.1174 0.019 Uiso 1 1 calc R U . . .
C26A C -0.37179(10) 0.51766(9) 0.24334(6) 0.01313(14) Uani 1 1 d . . . . .
C26B C -0.28202(10) 0.64240(9) 0.26324(6) 0.01309(14) Uani 1 1 d . . . . .
C26C C -0.24937(10) 0.70180(9) 0.19774(6) 0.01447(15) Uani 1 1 d . . . . .
O1 O -0.15633(9) 0.51844(8) 0.53839(5) 0.02291(15) Uani 1 1 d . . . . .
H100 H -0.1080 0.4498 0.5352 0.027 Uiso 1 1 d R U . . .
C27 C -0.27684(15) 0.50848(12) 0.58107(8) 0.0279(2) Uani 1 1 d . . . . .
H27A H -0.3360 0.4217 0.5525 0.042 Uiso 1 1 calc R U . . .
H27B H -0.3410 0.5791 0.5787 0.042 Uiso 1 1 calc R U . . .
H27C H -0.2362 0.5177 0.6412 0.042 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
C1 C2 1.3924(14) . ?
C1 C13C 1.4034(13) . ?
C1 H1 0.9500 . ?
C2 C3 1.3913(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3867(18) . ?
C3 H3 0.9500 . ?
C4 C4A 1.3995(14) . ?
C4 H4 0.9500 . ?
C4A C13C 1.4009(13) . ?
C4A C5 1.5066(14) . ?
C5 C6 1.5193(14) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N7 1.4758(13) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
N7 C8 1.3264(12) . ?
N7 H7 0.8800 . ?
C8 C8A 1.4706(12) . ?
C8 S1 1.7004(10) . ?
C8A N9 1.3830(11) . ?
C8A C13B 1.3906(12) . ?
N9 C9A 1.3676(12) . ?
N9 H9 0.8800 . ?
C9A C10 1.4000(13) . ?
C9A C13A 1.4125(12) . ?
C10 C11 1.3850(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.4122(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3829(14) . ?
C12 H12 0.9500 . ?
C13 C13A 1.4057(13) . ?
C13 H13 0.9500 . ?
C13A C13B 1.4354(12) . ?
C13B C13C 1.4722(12) . ?
C14 C15 1.3889(15) . ?
C14 C26C 1.4130(13) . ?
C14 H14 0.9500 . ?
C15 C16 1.3906(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.3820(17) . ?
C16 H16 0.9500 . ?
C17 C17A 1.4043(14) . ?
C17 H17 0.9500 . ?
C17A C26C 1.4111(13) . ?
C17A C18 1.5165(15) . ?
C18 C19 1.5128(15) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 N20 1.4671(12) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
N20 C21 1.3266(12) . ?
N20 H20 0.8800 . ?
C21 C21A 1.4572(12) . ?
C21 S2 1.6958(9) . ?
C21A N22 1.3794(12) . ?
C21A C26B 1.3940(13) . ?
N22 C22A 1.3685(12) . ?
N22 H22 0.8800 . ?
C22A C23 1.4049(13) . ?
C22A C26A 1.4148(13) . ?
C23 C24 1.3816(14) . ?
C23 H23 0.9500 . ?
C24 C25 1.4119(16) . ?
C24 H24 0.9500 . ?
C25 C26 1.3836(14) . ?
C25 H25 0.9500 . ?
C26 C26A 1.4145(13) . ?
C26 H26 0.9500 . ?
C26A C26B 1.4405(12) . ?
C26B C26C 1.4895(13) . ?
O1 C27 1.4287(14) . ?
O1 H100 0.8629 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

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
C2 C1 C13C 120.79(10) . . ?
C2 C1 H1 119.6 . . ?
C13C C1 H1 119.6 . . ?
C3 C2 C1 119.64(10) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 119.86(9) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C4A 121.19(10) . . ?
C3 C4 H4 119.4 . . ?
C4A C4 H4 119.4 . . ?
C4 C4A C13C 119.09(10) . . ?
C4 C4A C5 119.77(9) . . ?
C13C C4A C5 121.14(8) . . ?
C4A C5 C6 112.61(8) . . ?
C4A C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
C4A C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
N7 C6 C5 118.23(8) . . ?
N7 C6 H6A 107.8 . . ?
C5 C6 H6A 107.8 . . ?
N7 C6 H6B 107.8 . . ?
C5 C6 H6B 107.8 . . ?
H6A C6 H6B 107.1 . . ?
C8 N7 C6 134.55(8) . . ?
C8 N7 H7 112.7 . . ?
C6 N7 H7 112.7 . . ?
N7 C8 C8A 123.12(8) . . ?
N7 C8 S1 119.93(7) . . ?
C8A C8 S1 116.89(7) . . ?
N9 C8A C13B 109.07(8) . . ?
N9 C8A C8 118.36(8) . . ?
C13B C8A C8 131.30(8) . . ?
C9A N9 C8A 109.51(7) . . ?
C9A N9 H9 125.2 . . ?
C8A N9 H9 125.2 . . ?
N9 C9A C10 129.92(9) . . ?
N9 C9A C13A 107.77(8) . . ?
C10 C9A C13A 122.28(9) . . ?
C11 C10 C9A 116.88(9) . . ?
C11 C10 H10 121.6 . . ?
C9A C10 H10 121.6 . . ?
C10 C11 C12 121.80(9) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C13 C12 C11 120.93(9) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C13A 118.57(9) . . ?
C12 C13 H13 120.7 . . ?
C13A C13 H13 120.7 . . ?
C13 C13A C9A 119.49(8) . . ?
C13 C13A C13B 133.15(8) . . ?
C9A C13A C13B 107.32(8) . . ?
C8A C13B C13A 106.28(7) . . ?
C8A C13B C13C 128.92(8) . . ?
C13A C13B C13C 124.80(8) . . ?
C4A C13C C1 119.41(8) . . ?
C4A C13C C13B 120.05(8) . . ?
C1 C13C C13B 120.44(8) . . ?
C15 C14 C26C 122.19(10) . . ?
C15 C14 H14 118.9 . . ?
C26C C14 H14 118.9 . . ?
C14 C15 C16 119.27(10) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 119.32(10) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C17A 122.62(10) . . ?
C16 C17 H17 118.7 . . ?
C17A C17 H17 118.7 . . ?
C17 C17A C26C 118.41(9) . . ?
C17 C17A C18 114.87(9) . . ?
C26C C17A C18 126.63(9) . . ?
C19 C18 C17A 117.73(8) . . ?
C19 C18 H18A 107.9 . . ?
C17A C18 H18A 107.9 . . ?
C19 C18 H18B 107.9 . . ?
C17A C18 H18B 107.9 . . ?
H18A C18 H18B 107.2 . . ?
N20 C19 C18 113.51(8) . . ?
N20 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
N20 C19 H19B 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C21 N20 C19 124.82(8) . . ?
C21 N20 H20 117.6 . . ?
C19 N20 H20 117.6 . . ?
N20 C21 C21A 116.49(8) . . ?
N20 C21 S2 122.11(7) . . ?
C21A C21 S2 121.37(7) . . ?
N22 C21A C26B 110.37(8) . . ?
N22 C21A C21 119.83(8) . . ?
C26B C21A C21 129.80(8) . . ?
C22A N22 C21A 108.63(8) . . ?
C22A N22 H22 125.7 . . ?
C21A N22 H22 125.7 . . ?
N22 C22A C23 129.16(9) . . ?
N22 C22A C26A 108.24(8) . . ?
C23 C22A C26A 122.60(8) . . ?
C24 C23 C22A 117.02(9) . . ?
C24 C23 H23 121.5 . . ?
C22A C23 H23 121.5 . . ?
C23 C24 C25 121.57(9) . . ?
C23 C24 H24 119.2 . . ?
C25 C24 H24 119.2 . . ?
C26 C25 C24 121.37(9) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C25 C26 C26A 118.56(9) . . ?
C25 C26 H26 120.7 . . ?
C26A C26 H26 120.7 . . ?
C26 C26A C22A 118.88(8) . . ?
C26 C26A C26B 133.64(9) . . ?
C22A C26A C26B 107.46(8) . . ?
C21A C26B C26A 105.25(8) . . ?
C21A C26B C26C 128.98(8) . . ?
C26A C26B C26C 124.31(8) . . ?
C17A C26C C14 118.18(9) . . ?
C17A C26C C26B 127.54(8) . . ?
C14 C26C C26B 114.27(8) . . ?
C27 O1 H100 108.1 . . ?
O1 C27 H27A 109.5 . . ?
O1 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O1 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
C13C C1 C2 C3 0.65(15) . . . . ?
C1 C2 C3 C4 0.27(17) . . . . ?
C2 C3 C4 C4A -0.62(17) . . . . ?
C3 C4 C4A C13C 0.04(16) . . . . ?
C3 C4 C4A C5 -179.21(10) . . . . ?
C4 C4A C5 C6 90.27(11) . . . . ?
C13C C4A C5 C6 -88.97(11) . . . . ?
C4A C5 C6 N7 64.68(11) . . . . ?
C5 C6 N7 C8 24.77(16) . . . . ?
C6 N7 C8 C8A -19.59(16) . . . . ?
C6 N7 C8 S1 163.37(9) . . . . ?
N7 C8 C8A N9 146.51(9) . . . . ?
S1 C8 C8A N9 -36.36(11) . . . . ?
N7 C8 C8A C13B -47.96(15) . . . . ?
S1 C8 C8A C13B 129.16(9) . . . . ?
C13B C8A N9 C9A 0.91(11) . . . . ?
C8 C8A N9 C9A 169.45(8) . . . . ?
C8A N9 C9A C10 175.83(11) . . . . ?
C8A N9 C9A C13A -2.09(11) . . . . ?
N9 C9A C10 C11 -178.75(11) . . . . ?
C13A C9A C10 C11 -1.09(16) . . . . ?
C9A C10 C11 C12 -0.95(18) . . . . ?
C10 C11 C12 C13 1.64(18) . . . . ?
C11 C12 C13 C13A -0.23(15) . . . . ?
C12 C13 C13A C9A -1.75(14) . . . . ?
C12 C13 C13A C13B 175.84(10) . . . . ?
N9 C9A C13A C13 -179.41(8) . . . . ?
C10 C9A C13A C13 2.47(15) . . . . ?
N9 C9A C13A C13B 2.44(10) . . . . ?
C10 C9A C13A C13B -175.68(9) . . . . ?
N9 C8A C13B C13A 0.62(10) . . . . ?
C8 C8A C13B C13A -165.92(9) . . . . ?
N9 C8A C13B C13C -178.37(9) . . . . ?
C8 C8A C13B C13C 15.09(16) . . . . ?
C13 C13A C13B C8A -179.66(10) . . . . ?
C9A C13A C13B C8A -1.87(10) . . . . ?
C13 C13A C13B C13C -0.62(16) . . . . ?
C9A C13A C13B C13C 177.17(8) . . . . ?
C4 C4A C13C C1 0.86(14) . . . . ?
C5 C4A C13C C1 -179.89(9) . . . . ?
C4 C4A C13C C13B 177.21(9) . . . . ?
C5 C4A C13C C13B -3.55(13) . . . . ?
C2 C1 C13C C4A -1.22(14) . . . . ?
C2 C1 C13C C13B -177.54(9) . . . . ?
C8A C13B C13C C4A 51.78(13) . . . . ?
C13A C13B C13C C4A -127.03(10) . . . . ?
C8A C13B C13C C1 -131.92(10) . . . . ?
C13A C13B C13C C1 49.27(13) . . . . ?
C26C C14 C15 C16 0.15(17) . . . . ?
C14 C15 C16 C17 -0.39(17) . . . . ?
C15 C16 C17 C17A 0.02(17) . . . . ?
C16 C17 C17A C26C 0.59(15) . . . . ?
C16 C17 C17A C18 -176.26(10) . . . . ?
C17 C17A C18 C19 -159.08(9) . . . . ?
C26C C17A C18 C19 24.38(14) . . . . ?
C17A C18 C19 N20 54.49(12) . . . . ?
C18 C19 N20 C21 -107.99(11) . . . . ?
C19 N20 C21 C21A 20.47(13) . . . . ?
C19 N20 C21 S2 -157.94(8) . . . . ?
N20 C21 C21A N22 -140.12(9) . . . . ?
S2 C21 C21A N22 38.30(11) . . . . ?
N20 C21 C21A C26B 38.55(14) . . . . ?
S2 C21 C21A C26B -143.02(9) . . . . ?
C26B C21A N22 C22A -2.37(10) . . . . ?
C21 C21A N22 C22A 176.55(8) . . . . ?
C21A N22 C22A C23 -177.74(9) . . . . ?
C21A N22 C22A C26A 1.97(10) . . . . ?
N22 C22A C23 C24 179.02(10) . . . . ?
C26A C22A C23 C24 -0.65(14) . . . . ?
C22A C23 C24 C25 0.38(16) . . . . ?
C23 C24 C25 C26 0.46(17) . . . . ?
C24 C25 C26 C26A -1.02(15) . . . . ?
C25 C26 C26A C22A 0.73(13) . . . . ?
C25 C26 C26A C26B -177.63(10) . . . . ?
N22 C22A C26A C26 -179.63(8) . . . . ?
C23 C22A C26A C26 0.10(14) . . . . ?
N22 C22A C26A C26B -0.88(10) . . . . ?
C23 C22A C26A C26B 178.86(9) . . . . ?
N22 C21A C26B C26A 1.75(10) . . . . ?
C21 C21A C26B C26A -177.02(9) . . . . ?
N22 C21A C26B C26C -164.72(9) . . . . ?
C21 C21A C26B C26C 16.51(16) . . . . ?
C26 C26A C26B C21A 177.97(10) . . . . ?
C22A C26A C26B C21A -0.52(10) . . . . ?
C26 C26A C26B C26C -14.75(16) . . . . ?
C22A C26A C26B C26C 166.76(8) . . . . ?
C17 C17A C26C C14 -0.80(13) . . . . ?
C18 C17A C26C C14 175.64(9) . . . . ?
C17 C17A C26C C26B 177.62(9) . . . . ?
C18 C17A C26C C26B -5.94(15) . . . . ?
C15 C14 C26C C17A 0.45(15) . . . . ?
C15 C14 C26C C26B -178.18(10) . . . . ?
C21A C26B C26C C17A -59.11(15) . . . . ?
C26A C26B C26C C17A 136.75(10) . . . . ?
C21A C26B C26C C14 119.36(11) . . . . ?
C26A C26B C26C C14 -44.78(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6A S2 0.99 2.72 3.6255(10) 152.2 1_545
N7 H7 S1 0.88 2.57 3.3595(8) 150.0 2_656
N9 H9 S2 0.88 2.74 3.4990(9) 145.8 2_566
C19 H19B N7 0.99 2.69 3.2824(13) 118.5 1_465
N20 H20 S2 0.88 2.63 3.3184(8) 136.4 2_576
N22 H22 O1 0.88 2.01 2.8665(11) 164.7 .
O1 H100 S2 0.86 2.52 3.3620(8) 164.5 2_566

_refine_diff_density_max         0.557
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.064

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_chwi685
_database_code_depnum_ccdc_archive 'CCDC 2261962'
loop_
_audit_author_name
_audit_author_address
'Vladimir Arion'
;University of Vienna
Austria
;
_audit_update_record             
;
2023-05-10 deposited with the CCDC.	2023-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 Br N5'
_chemical_formula_sum            'C24 H20 Br N5'
_chemical_formula_weight         458.36

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   8.0799(3)
_cell_length_b                   15.5637(5)
_cell_length_c                   15.6684(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1970.35(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    3461
_cell_measurement_theta_min      2.841
_cell_measurement_theta_max      28.927

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.028
_exptl_crystal_size_min          0.019
_exptl_absorpt_coefficient_mu    2.109
_shelx_estimated_absorpt_T_min   0.509
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4749
_exptl_absorpt_correction_T_max  0.6042
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11561
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.600
_diffrn_reflns_theta_max         30.049
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.782
_diffrn_reflns_point_group_measured_fraction_full 0.903
_reflns_number_total             4521
_reflns_number_gt                3478
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.539
_reflns_Friedel_fraction_max     0.567
_reflns_Friedel_fraction_full    0.804

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0708P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.016(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4521
_refine_ls_number_parameters     272
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1145
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Br Br 0.58838(6) 0.68148(3) 0.17039(5) 0.02893(16) Uani 1 1 d . . . . .
C1 C 0.2179(6) 0.5703(3) -0.1241(3) 0.0153(10) Uani 1 1 d . . . . .
H1 H 0.2902 0.5346 -0.0920 0.018 Uiso 1 1 calc R U . . .
C2 C 0.2585(6) 0.5909(3) -0.2080(3) 0.0182(10) Uani 1 1 d . . . . .
H2 H 0.3561 0.5686 -0.2335 0.022 Uiso 1 1 calc R U . . .
C3 C 0.1529(7) 0.6454(3) -0.2543(3) 0.0206(11) Uani 1 1 d . . . . .
H3 H 0.1788 0.6603 -0.3115 0.025 Uiso 1 1 calc R U . . .
C4 C 0.0118(7) 0.6770(3) -0.2165(3) 0.0185(10) Uani 1 1 d . . . . .
H4 H -0.0591 0.7134 -0.2486 0.022 Uiso 1 1 calc R U . . .
C4A C -0.0301(7) 0.6571(3) -0.1323(3) 0.0162(10) Uani 1 1 d . . . . .
C5 C -0.1832(6) 0.6918(3) -0.0920(3) 0.0170(10) Uani 1 1 d . . . . .
H5A H -0.2077 0.7490 -0.1166 0.020 Uiso 1 1 calc R U . . .
H5B H -0.1639 0.6993 -0.0301 0.020 Uiso 1 1 calc R U . . .
C6 C -0.3327(6) 0.6330(3) -0.1052(4) 0.0211(11) Uani 1 1 d . . . . .
H6A H -0.4256 0.6550 -0.0702 0.025 Uiso 1 1 calc R U . . .
H6B H -0.3669 0.6364 -0.1657 0.025 Uiso 1 1 calc R U . . .
N7 N -0.3051(5) 0.5423(2) -0.0833(3) 0.0185(9) Uani 1 1 d . . . . .
H7 H -0.3857 0.5143 -0.0973 0.022 Uiso 1 1 d R U . . .
C8 C -0.2620(6) 0.5137(3) -0.0026(3) 0.0162(10) Uani 1 1 d . . . . .
C8A C -0.1075(6) 0.5415(3) 0.0366(3) 0.0150(10) Uani 1 1 d . . . . .
N9 N -0.0822(5) 0.5255(3) 0.1226(3) 0.0181(9) Uani 1 1 d . . . . .
H9 H -0.1557 0.5021 0.1569 0.022 Uiso 1 1 calc R U . . .
C9A C 0.0745(6) 0.5514(3) 0.1469(3) 0.0133(10) Uani 1 1 d . . . . .
C10 C 0.1508(7) 0.5507(3) 0.2260(3) 0.0190(10) Uani 1 1 d . . . . .
H10 H 0.0994 0.5255 0.2745 0.023 Uiso 1 1 calc R U . . .
C11 C 0.3049(7) 0.5884(3) 0.2312(3) 0.0216(11) Uani 1 1 d . . . . .
H11 H 0.3610 0.5900 0.2845 0.026 Uiso 1 1 calc R U . . .
C12 C 0.3797(6) 0.6244(3) 0.1590(4) 0.0198(11) Uani 1 1 d . . . . .
C13 C 0.3084(7) 0.6221(3) 0.0796(3) 0.0181(10) Uani 1 1 d . . . . .
H13 H 0.3633 0.6453 0.0312 0.022 Uiso 1 1 calc R U . . .
C13A C 0.1504(6) 0.5841(3) 0.0725(3) 0.0162(10) Uani 1 1 d . . . . .
N14 N -0.3463(5) 0.4556(3) 0.0394(3) 0.0186(9) Uani 1 1 d . . . . .
C13B C 0.0366(6) 0.5763(3) 0.0030(3) 0.0149(10) Uani 1 1 d . . . . .
C13C C 0.0734(5) 0.6009(3) -0.0862(3) 0.0127(9) Uani 1 1 d . . . . .
N15 N -0.4890(5) 0.4311(2) -0.0061(3) 0.0185(9) Uani 1 1 d . . . . .
C16 C -0.5967(6) 0.3892(3) 0.0390(4) 0.0179(10) Uani 1 1 d . . . . .
C17 C -0.7486(6) 0.3630(3) -0.0086(3) 0.0158(10) Uani 1 1 d . . . . .
N18 N -0.8831(6) 0.3443(3) 0.0392(3) 0.0213(10) Uani 1 1 d . . . . .
C19 C -1.0218(8) 0.3261(3) -0.0021(4) 0.0240(12) Uani 1 1 d . . . . .
H19 H -1.1175 0.3137 0.0309 0.029 Uiso 1 1 calc R U . . .
C20 C -1.0368(8) 0.3240(3) -0.0895(4) 0.0261(13) Uani 1 1 d . . . . .
H20 H -1.1407 0.3127 -0.1156 0.031 Uiso 1 1 calc R U . . .
C21 C -0.8981(7) 0.3385(3) -0.1384(4) 0.0260(12) Uani 1 1 d . . . . .
H21 H -0.9027 0.3345 -0.1988 0.031 Uiso 1 1 calc R U . . .
C22 C -0.7518(7) 0.3590(3) -0.0974(4) 0.0211(11) Uani 1 1 d . . . . .
H22 H -0.6545 0.3702 -0.1295 0.025 Uiso 1 1 calc R U . . .
C23 C -0.5873(6) 0.3697(3) 0.1335(4) 0.0230(11) Uani 1 1 d . . . . .
H23A H -0.5784 0.4236 0.1655 0.035 Uiso 1 1 calc R U . . .
H23B H -0.4899 0.3340 0.1449 0.035 Uiso 1 1 calc R U . . .
H23C H -0.6873 0.3389 0.1512 0.035 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
Br C12 1.915(5) . ?
C1 C2 1.393(7) . ?
C1 C13C 1.394(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.405(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(8) . ?
C3 H3 0.9500 . ?
C4 C4A 1.398(7) . ?
C4 H4 0.9500 . ?
C4A C13C 1.408(7) . ?
C4A C5 1.490(7) . ?
C5 C6 1.529(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N7 1.471(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
N7 C8 1.384(6) . ?
N7 H7 0.8129 . ?
C8 N14 1.310(6) . ?
C8 C8A 1.457(7) . ?
C8A N9 1.384(6) . ?
C8A C13B 1.388(7) . ?
N9 C9A 1.383(6) . ?
N9 H9 0.8800 . ?
C9A C10 1.384(7) . ?
C9A C13A 1.413(7) . ?
C10 C11 1.379(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.400(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.370(8) . ?
C13 C13A 1.412(7) . ?
C13 H13 0.9500 . ?
C13A C13B 1.429(7) . ?
N14 N15 1.408(6) . ?
C13B C13C 1.480(7) . ?
N15 C16 1.296(7) . ?
C16 C17 1.492(7) . ?
C16 C23 1.513(8) . ?
C17 N18 1.352(7) . ?
C17 C22 1.393(7) . ?
N18 C19 1.325(8) . ?
C19 C20 1.375(9) . ?
C19 H19 0.9500 . ?
C20 C21 1.376(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.382(8) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
C2 C1 C13C 121.3(5) . . ?
C2 C1 H1 119.3 . . ?
C13C C1 H1 119.3 . . ?
C1 C2 C3 118.9(5) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 119.8(5) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C4A 121.8(5) . . ?
C3 C4 H4 119.1 . . ?
C4A C4 H4 119.1 . . ?
C4 C4A C13C 118.5(5) . . ?
C4 C4A C5 121.4(5) . . ?
C13C C4A C5 120.1(5) . . ?
C4A C5 C6 112.5(4) . . ?
C4A C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
C4A C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
N7 C6 C5 115.0(4) . . ?
N7 C6 H6A 108.5 . . ?
C5 C6 H6A 108.5 . . ?
N7 C6 H6B 108.5 . . ?
C5 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
C8 N7 C6 124.0(4) . . ?
C8 N7 H7 106.1 . . ?
C6 N7 H7 109.2 . . ?
N14 C8 N7 123.3(4) . . ?
N14 C8 C8A 116.0(4) . . ?
N7 C8 C8A 120.4(4) . . ?
N9 C8A C13B 108.4(4) . . ?
N9 C8A C8 118.9(4) . . ?
C13B C8A C8 132.4(5) . . ?
C9A N9 C8A 110.6(4) . . ?
C9A N9 H9 124.7 . . ?
C8A N9 H9 124.7 . . ?
N9 C9A C10 130.8(4) . . ?
N9 C9A C13A 105.9(4) . . ?
C10 C9A C13A 123.3(5) . . ?
C11 C10 C9A 116.9(5) . . ?
C11 C10 H10 121.6 . . ?
C9A C10 H10 121.6 . . ?
C10 C11 C12 120.8(5) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 122.8(5) . . ?
C13 C12 Br 117.8(4) . . ?
C11 C12 Br 119.3(4) . . ?
C12 C13 C13A 117.6(5) . . ?
C12 C13 H13 121.2 . . ?
C13A C13 H13 121.2 . . ?
C13 C13A C9A 118.5(5) . . ?
C13 C13A C13B 132.7(5) . . ?
C9A C13A C13B 108.6(4) . . ?
C8 N14 N15 111.1(4) . . ?
C8A C13B C13A 106.5(4) . . ?
C8A C13B C13C 128.9(4) . . ?
C13A C13B C13C 124.6(4) . . ?
C1 C13C C4A 119.5(5) . . ?
C1 C13C C13B 118.8(4) . . ?
C4A C13C C13B 121.7(4) . . ?
C16 N15 N14 114.3(4) . . ?
N15 C16 C17 114.6(5) . . ?
N15 C16 C23 126.8(5) . . ?
C17 C16 C23 118.4(4) . . ?
N18 C17 C22 121.9(5) . . ?
N18 C17 C16 116.3(5) . . ?
C22 C17 C16 121.8(5) . . ?
C19 N18 C17 117.1(5) . . ?
N18 C19 C20 124.5(6) . . ?
N18 C19 H19 117.8 . . ?
C20 C19 H19 117.8 . . ?
C19 C20 C21 118.5(5) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C20 C21 C22 118.5(6) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
C21 C22 C17 119.4(5) . . ?
C21 C22 H22 120.3 . . ?
C17 C22 H22 120.3 . . ?
C16 C23 H23A 109.5 . . ?
C16 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C16 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C13C C1 C2 C3 1.5(7) . . . . ?
C1 C2 C3 C4 -0.2(7) . . . . ?
C2 C3 C4 C4A 0.5(8) . . . . ?
C3 C4 C4A C13C -2.0(7) . . . . ?
C3 C4 C4A C5 180.0(5) . . . . ?
C4 C4A C5 C6 89.8(6) . . . . ?
C13C C4A C5 C6 -88.2(6) . . . . ?
C4A C5 C6 N7 50.1(7) . . . . ?
C5 C6 N7 C8 60.7(7) . . . . ?
C6 N7 C8 N14 124.7(5) . . . . ?
C6 N7 C8 C8A -61.6(7) . . . . ?
N14 C8 C8A N9 -17.9(7) . . . . ?
N7 C8 C8A N9 167.9(4) . . . . ?
N14 C8 C8A C13B 154.8(5) . . . . ?
N7 C8 C8A C13B -19.4(8) . . . . ?
C13B C8A N9 C9A 1.8(5) . . . . ?
C8 C8A N9 C9A 176.1(4) . . . . ?
C8A N9 C9A C10 177.4(5) . . . . ?
C8A N9 C9A C13A -0.6(5) . . . . ?
N9 C9A C10 C11 -174.3(5) . . . . ?
C13A C9A C10 C11 3.5(8) . . . . ?
C9A C10 C11 C12 -0.8(8) . . . . ?
C10 C11 C12 C13 -2.1(8) . . . . ?
C10 C11 C12 Br 176.7(4) . . . . ?
C11 C12 C13 C13A 2.1(8) . . . . ?
Br C12 C13 C13A -176.6(4) . . . . ?
C12 C13 C13A C9A 0.5(7) . . . . ?
C12 C13 C13A C13B 174.7(5) . . . . ?
N9 C9A C13A C13 174.8(5) . . . . ?
C10 C9A C13A C13 -3.4(8) . . . . ?
N9 C9A C13A C13B -0.7(5) . . . . ?
C10 C9A C13A C13B -178.9(5) . . . . ?
N7 C8 N14 N15 -3.6(7) . . . . ?
C8A C8 N14 N15 -177.5(4) . . . . ?
N9 C8A C13B C13A -2.1(5) . . . . ?
C8 C8A C13B C13A -175.4(5) . . . . ?
N9 C8A C13B C13C 177.4(5) . . . . ?
C8 C8A C13B C13C 4.1(9) . . . . ?
C13 C13A C13B C8A -172.9(5) . . . . ?
C9A C13A C13B C8A 1.8(5) . . . . ?
C13 C13A C13B C13C 7.6(9) . . . . ?
C9A C13A C13B C13C -177.8(4) . . . . ?
C2 C1 C13C C4A -3.0(7) . . . . ?
C2 C1 C13C C13B 179.7(4) . . . . ?
C4 C4A C13C C1 3.2(7) . . . . ?
C5 C4A C13C C1 -178.7(4) . . . . ?
C4 C4A C13C C13B -179.6(4) . . . . ?
C5 C4A C13C C13B -1.5(7) . . . . ?
C8A C13B C13C C1 -129.0(5) . . . . ?
C13A C13B C13C C1 50.4(7) . . . . ?
C8A C13B C13C C4A 53.8(7) . . . . ?
C13A C13B C13C C4A -126.8(5) . . . . ?
C8 N14 N15 C16 -165.2(4) . . . . ?
N14 N15 C16 C17 179.9(4) . . . . ?
N14 N15 C16 C23 3.7(7) . . . . ?
N15 C16 C17 N18 -159.9(4) . . . . ?
C23 C16 C17 N18 16.6(6) . . . . ?
N15 C16 C17 C22 19.5(7) . . . . ?
C23 C16 C17 C22 -163.9(5) . . . . ?
C22 C17 N18 C19 -3.5(7) . . . . ?
C16 C17 N18 C19 176.0(4) . . . . ?
C17 N18 C19 C20 0.9(8) . . . . ?
N18 C19 C20 C21 2.5(8) . . . . ?
C19 C20 C21 C22 -3.3(8) . . . . ?
C20 C21 C22 C17 1.0(8) . . . . ?
N18 C17 C22 C21 2.6(8) . . . . ?
C16 C17 C22 C21 -176.8(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N7 H7 N15 0.81 2.10 2.582(6) 117.6 .

_refine_diff_density_max         0.566
_refine_diff_density_min         -0.672
_refine_diff_density_rms         0.088

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_chwi1084
_database_code_depnum_ccdc_archive 'CCDC 2261963'
loop_
_audit_author_name
_audit_author_address
'Vladimir Arion'
;University of Vienna
Austria
;
_audit_update_record             
;
2023-05-10 deposited with the CCDC.	2023-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 Br N2 O2, C18 H15 Br N2 O'
_chemical_formula_sum            'C39 H36 Br2 N4 O3'
_chemical_formula_weight         768.54

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   11.5688(12)
_cell_length_b                   10.8490(10)
_cell_length_c                   27.689(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.143(11)
_cell_angle_gamma                90
_cell_volume                     3431.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    39441
_cell_measurement_theta_min      1.49
_cell_measurement_theta_max      30.61

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             1568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.600
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    2.407
_shelx_estimated_absorpt_T_min   0.197
_shelx_estimated_absorpt_T_max   0.532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.0125
_exptl_absorpt_correction_T_max  0.0244
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32811
_diffrn_reflns_av_unetI/netI     0.1594
_diffrn_reflns_av_R_equivalents  0.1043
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.783
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6485
_reflns_number_gt                3111
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)'
_computing_cell_refinement       'X-Area Recipe 1.36.0-0 (STOE, 2020)'
_computing_data_reduction        
'X-Area Integrate 1.78.3.0; X-Area LANA 1.83.8.0 (STOE, 2020)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0742P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6485
_refine_ls_number_parameters     434
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1491
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1510
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_restrained_S_all      0.907
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.31919(6) 0.15606(6) 0.48132(3) 0.0302(2) Uani 1 1 d . . . . .
Br2 Br 0.80556(6) 1.09024(6) 0.61567(3) 0.0382(2) Uani 1 1 d . . . . .
N30 N 0.6810(4) 0.6920(4) 0.74860(19) 0.0237(13) Uani 1 1 d . . . . .
O4 O 0.5866(3) 0.4328(4) 0.73753(16) 0.0285(11) Uani 1 1 d . . . . .
N10 N 0.4530(4) 0.4999(4) 0.64928(19) 0.0224(12) Uani 1 1 d . . . . .
H10 H 0.5038 0.4965 0.6765 0.027 Uiso 1 1 calc R U . . .
C21 C 0.7187(5) 0.5265(5) 0.6029(2) 0.0225(15) Uani 1 1 d . . . . .
H21 H 0.6480 0.5727 0.5979 0.027 Uiso 1 1 calc R U . . .
O36 O 0.6905(3) 0.6220(3) 0.82973(16) 0.0263(11) Uani 1 1 d . . . . .
C30A C 0.7059(5) 0.7967(5) 0.7231(2) 0.0187(14) Uani 1 1 d . . . . .
C12 C 0.4625(5) 0.2312(5) 0.5691(2) 0.0242(16) Uani 1 1 d . . . . .
H12 H 0.5032 0.1568 0.5650 0.029 Uiso 1 1 calc R U . . .
C14 C 0.3102(5) 0.3746(5) 0.5370(2) 0.0204(15) Uani 1 1 d . . . . .
H14 H 0.2465 0.3965 0.5124 0.024 Uiso 1 1 calc R U . . .
C10A C 0.4374(5) 0.4125(5) 0.6134(2) 0.0212(15) Uani 1 1 d . . . . .
C29 C 0.6914(6) 0.4632(5) 0.7402(2) 0.0240(15) Uani 1 1 d . . . . .
O14 O 0.3134(4) 0.6725(4) 0.70688(16) 0.0318(12) Uani 1 1 d . . . . .
N28 N 0.7791(4) 0.3862(4) 0.75512(19) 0.0247(13) Uani 1 1 d . . . . .
H28 H 0.7622 0.3071 0.7543 0.030 Uiso 1 1 calc R U . . .
C14B C 0.3084(5) 0.5712(5) 0.5912(2) 0.0226(15) Uani 1 1 d . . . . .
C34C C 0.7980(5) 0.5421(5) 0.6464(2) 0.0236(15) Uani 1 1 d . . . . .
C22 C 0.7420(6) 0.4446(5) 0.5671(2) 0.0289(17) Uani 1 1 d . . . . .
H22 H 0.6868 0.4336 0.5382 0.035 Uiso 1 1 calc R U . . .
C11 C 0.4978(5) 0.3030(5) 0.6098(2) 0.0210(15) Uani 1 1 d . . . . .
H11 H 0.5607 0.2787 0.6343 0.025 Uiso 1 1 calc R U . . .
C35 C 0.6236(5) 0.6854(6) 0.7914(2) 0.0292(17) Uani 1 1 d . . . . .
H35A H 0.6086 0.7700 0.8023 0.035 Uiso 1 1 calc R U . . .
H35B H 0.5471 0.6435 0.7826 0.035 Uiso 1 1 calc R U . . .
C34B C 0.7650(5) 0.6253(5) 0.6843(2) 0.0193(14) Uani 1 1 d . . . . .
C24A C 0.9039(5) 0.4750(5) 0.6539(2) 0.0204(15) Uani 1 1 d . . . . .
C34A C 0.7562(5) 0.7576(5) 0.6822(2) 0.0191(14) Uani 1 1 d . . . . .
C13 C 0.3687(5) 0.2653(5) 0.5339(2) 0.0211(15) Uani 1 1 d . . . . .
C14A C 0.3455(5) 0.4525(5) 0.5764(2) 0.0176(14) Uani 1 1 d . . . . .
C9A C 0.3747(5) 0.5950(5) 0.6355(2) 0.0224(15) Uani 1 1 d . . . . .
N8 N 0.3966(4) 0.8074(4) 0.66004(19) 0.0273(14) Uani 1 1 d . . . . .
H8 H 0.3721 0.8690 0.6764 0.033 Uiso 1 1 calc R U . . .
C23 C 0.8451(6) 0.3797(5) 0.5738(3) 0.0298(17) Uani 1 1 d . . . . .
H23 H 0.8623 0.3246 0.5492 0.036 Uiso 1 1 calc R U . . .
C27 C 0.9006(5) 0.4197(6) 0.7727(2) 0.0262(16) Uani 1 1 d . . . . .
H27A H 0.9264 0.3759 0.8039 0.031 Uiso 1 1 calc R U . . .
H27B H 0.9036 0.5091 0.7799 0.031 Uiso 1 1 calc R U . . .
C7 C 0.4723(5) 0.8393(5) 0.6244(2) 0.0257(16) Uani 1 1 d . . . . .
H7A H 0.5142 0.7639 0.6168 0.031 Uiso 1 1 calc R U . . .
H7B H 0.5319 0.8987 0.6398 0.031 Uiso 1 1 calc R U . . .
C24 C 0.9245(5) 0.3954(5) 0.6169(3) 0.0279(17) Uani 1 1 d . . . . .
H24 H 0.9955 0.3499 0.6211 0.033 Uiso 1 1 calc R U . . .
C38 C 0.8521(5) 0.6160(6) 0.8946(2) 0.0359(18) Uani 1 1 d . . . . .
H38A H 0.8694 0.5333 0.8834 0.054 Uiso 1 1 calc R U . . .
H38B H 0.8013 0.6093 0.9197 0.054 Uiso 1 1 calc R U . . .
H38C H 0.9253 0.6571 0.9085 0.054 Uiso 1 1 calc R U . . .
C26 C 0.9875(5) 0.3923(6) 0.7387(2) 0.0279(17) Uani 1 1 d . . . . .
H26A H 0.9669 0.3121 0.7225 0.033 Uiso 1 1 calc R U . . .
H26B H 1.0663 0.3836 0.7585 0.033 Uiso 1 1 calc R U . . .
C37 C 0.7911(5) 0.6898(6) 0.8522(2) 0.0281(17) Uani 1 1 d . . . . .
H37A H 0.7669 0.7708 0.8637 0.034 Uiso 1 1 calc R U . . .
H37B H 0.8447 0.7043 0.8282 0.034 Uiso 1 1 calc R U . . .
C25 C 0.9938(5) 0.4895(6) 0.6991(2) 0.0260(16) Uani 1 1 d . . . . .
H25A H 0.9843 0.5720 0.7132 0.031 Uiso 1 1 calc R U . . .
H25B H 1.0726 0.4865 0.6895 0.031 Uiso 1 1 calc R U . . .
C29A C 0.7191(5) 0.5903(5) 0.7250(2) 0.0223(15) Uani 1 1 d . . . . .
C34 C 0.7884(5) 0.8444(5) 0.6502(2) 0.0205(14) Uani 1 1 d . . . . .
H34 H 0.8233 0.8203 0.6228 0.025 Uiso 1 1 calc R U . . .
C33 C 0.7682(5) 0.9669(6) 0.6593(2) 0.0240(15) Uani 1 1 d . . . . .
C31 C 0.6870(5) 0.9204(6) 0.7321(2) 0.0248(15) Uani 1 1 d . . . . .
H31 H 0.6520 0.9456 0.7593 0.030 Uiso 1 1 calc R U . . .
C6 C 0.4110(5) 0.8946(5) 0.5764(2) 0.0200(15) Uani 1 1 d . . . . .
H6A H 0.4698 0.9418 0.5616 0.024 Uiso 1 1 calc R U . . .
H6B H 0.3519 0.9542 0.5842 0.024 Uiso 1 1 calc R U . . .
C14C C 0.2111(5) 0.6491(5) 0.5673(2) 0.0228(15) Uani 1 1 d . . . . .
C1 C 0.0961(5) 0.6129(5) 0.5702(2) 0.0262(16) Uani 1 1 d . . . . .
H1 H 0.0824 0.5359 0.5847 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3502(5) 0.8054(5) 0.5378(2) 0.0260(16) Uani 1 1 d . . . . .
H5A H 0.3429 0.8458 0.5054 0.031 Uiso 1 1 calc R U . . .
H5B H 0.4009 0.7321 0.5370 0.031 Uiso 1 1 calc R U . . .
C4A C 0.2297(5) 0.7622(5) 0.5455(2) 0.0200(15) Uani 1 1 d . . . . .
C4 C 0.1326(5) 0.8354(6) 0.5278(2) 0.0284(16) Uani 1 1 d . . . . .
H4 H 0.1444 0.9121 0.5127 0.034 Uiso 1 1 calc R U . . .
C2 C 0.0028(5) 0.6871(6) 0.5523(3) 0.0332(18) Uani 1 1 d . . . . .
H2 H -0.0746 0.6609 0.5543 0.040 Uiso 1 1 calc R U . . .
C3 C 0.0207(5) 0.7990(6) 0.5315(2) 0.0310(17) Uani 1 1 d . . . . .
H3 H -0.0439 0.8508 0.5197 0.037 Uiso 1 1 calc R U . . .
C9 C 0.3605(5) 0.6950(5) 0.6705(2) 0.0219(15) Uani 1 1 d . . . . .
C32 C 0.7208(5) 1.0048(5) 0.7001(2) 0.0256(16) Uani 1 1 d . . . . .
H32 H 0.7118 1.0903 0.7059 0.031 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 C13 1.895(6) . ?
Br2 C33 1.898(6) . ?
N30 C29A 1.389(7) . ?
N30 C30A 1.392(7) . ?
N30 C35 1.450(7) . ?
O4 C29 1.248(7) . ?
N10 C10A 1.365(7) . ?
N10 C9A 1.385(7) . ?
N10 H10 0.8800 . ?
C21 C22 1.389(8) . ?
C21 C34C 1.404(8) . ?
C21 H21 0.9500 . ?
O36 C35 1.392(7) . ?
O36 C37 1.433(7) . ?
C30A C31 1.389(8) . ?
C30A C34A 1.418(8) . ?
C12 C11 1.376(8) . ?
C12 C13 1.389(8) . ?
C12 H12 0.9500 . ?
C14 C13 1.374(7) . ?
C14 C14A 1.390(8) . ?
C14 H14 0.9500 . ?
C10A C11 1.390(7) . ?
C10A C14A 1.422(8) . ?
C29 N28 1.328(7) . ?
C29 C29A 1.491(8) . ?
O14 C9 1.242(7) . ?
N28 C27 1.459(7) . ?
N28 H28 0.8800 . ?
C14B C9A 1.363(8) . ?
C14B C14A 1.438(8) . ?
C14B C14C 1.477(8) . ?
C34C C24A 1.412(8) . ?
C34C C34B 1.479(8) . ?
C22 C23 1.372(8) . ?
C22 H22 0.9500 . ?
C11 H11 0.9500 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C34B C29A 1.373(8) . ?
C34B C34A 1.440(7) . ?
C24A C24 1.390(8) . ?
C24A C25 1.502(8) . ?
C34A C34 1.383(7) . ?
C9A C9 1.483(8) . ?
N8 C9 1.335(7) . ?
N8 C7 1.462(7) . ?
N8 H8 0.8800 . ?
C23 C24 1.396(9) . ?
C23 H23 0.9500 . ?
C27 C26 1.513(8) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C7 C6 1.526(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C24 H24 0.9500 . ?
C38 C37 1.503(8) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C26 C25 1.531(8) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C34 C33 1.379(7) . ?
C34 H34 0.9500 . ?
C33 C32 1.396(8) . ?
C31 C32 1.373(8) . ?
C31 H31 0.9500 . ?
C6 C5 1.528(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C14C C4A 1.400(8) . ?
C14C C1 1.401(7) . ?
C1 C2 1.374(8) . ?
C1 H1 0.9500 . ?
C5 C4A 1.518(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C4A C4 1.400(8) . ?
C4 C3 1.373(8) . ?
C4 H4 0.9500 . ?
C2 C3 1.373(8) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C32 H32 0.9500 . ?

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
C29A N30 C30A 107.6(5) . . ?
C29A N30 C35 124.4(5) . . ?
C30A N30 C35 127.9(5) . . ?
C10A N10 C9A 108.1(5) . . ?
C10A N10 H10 125.9 . . ?
C9A N10 H10 125.9 . . ?
C22 C21 C34C 121.0(6) . . ?
C22 C21 H21 119.5 . . ?
C34C C21 H21 119.5 . . ?
C35 O36 C37 113.1(5) . . ?
C31 C30A N30 130.2(6) . . ?
C31 C30A C34A 121.9(5) . . ?
N30 C30A C34A 107.8(5) . . ?
C11 C12 C13 121.4(6) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C13 C14 C14A 119.1(6) . . ?
C13 C14 H14 120.4 . . ?
C14A C14 H14 120.4 . . ?
N10 C10A C11 129.5(6) . . ?
N10 C10A C14A 108.1(5) . . ?
C11 C10A C14A 122.4(6) . . ?
O4 C29 N28 122.6(6) . . ?
O4 C29 C29A 118.6(5) . . ?
N28 C29 C29A 118.8(5) . . ?
C29 N28 C27 126.5(5) . . ?
C29 N28 H28 116.8 . . ?
C27 N28 H28 116.8 . . ?
C9A C14B C14A 106.0(5) . . ?
C9A C14B C14C 125.1(6) . . ?
C14A C14B C14C 128.7(6) . . ?
C21 C34C C24A 119.8(6) . . ?
C21 C34C C34B 118.4(5) . . ?
C24A C34C C34B 121.8(6) . . ?
C23 C22 C21 119.7(7) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C12 C11 C10A 117.1(6) . . ?
C12 C11 H11 121.5 . . ?
C10A C11 H11 121.5 . . ?
O36 C35 N30 112.1(5) . . ?
O36 C35 H35A 109.2 . . ?
N30 C35 H35A 109.2 . . ?
O36 C35 H35B 109.2 . . ?
N30 C35 H35B 109.2 . . ?
H35A C35 H35B 107.9 . . ?
C29A C34B C34A 106.0(5) . . ?
C29A C34B C34C 126.2(5) . . ?
C34A C34B C34C 127.1(5) . . ?
C24 C24A C34C 117.3(6) . . ?
C24 C24A C25 120.2(5) . . ?
C34C C24A C25 122.5(6) . . ?
C34 C34A C30A 119.6(5) . . ?
C34 C34A C34B 132.9(6) . . ?
C30A C34A C34B 107.5(5) . . ?
C14 C13 C12 121.7(6) . . ?
C14 C13 Br1 119.7(5) . . ?
C12 C13 Br1 118.7(4) . . ?
C14 C14A C10A 118.2(5) . . ?
C14 C14A C14B 134.9(6) . . ?
C10A C14A C14B 106.9(5) . . ?
C14B C9A N10 110.9(5) . . ?
C14B C9A C9 128.5(6) . . ?
N10 C9A C9 120.0(6) . . ?
C9 N8 C7 127.2(5) . . ?
C9 N8 H8 116.4 . . ?
C7 N8 H8 116.4 . . ?
C22 C23 C24 119.5(6) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
N28 C27 C26 116.3(5) . . ?
N28 C27 H27A 108.2 . . ?
C26 C27 H27A 108.2 . . ?
N28 C27 H27B 108.2 . . ?
C26 C27 H27B 108.2 . . ?
H27A C27 H27B 107.4 . . ?
N8 C7 C6 115.8(5) . . ?
N8 C7 H7A 108.3 . . ?
C6 C7 H7A 108.3 . . ?
N8 C7 H7B 108.3 . . ?
C6 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C24A C24 C23 122.7(6) . . ?
C24A C24 H24 118.7 . . ?
C23 C24 H24 118.7 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C27 C26 C25 115.0(5) . . ?
C27 C26 H26A 108.5 . . ?
C25 C26 H26A 108.5 . . ?
C27 C26 H26B 108.5 . . ?
C25 C26 H26B 108.5 . . ?
H26A C26 H26B 107.5 . . ?
O36 C37 C38 108.2(5) . . ?
O36 C37 H37A 110.1 . . ?
C38 C37 H37A 110.1 . . ?
O36 C37 H37B 110.1 . . ?
C38 C37 H37B 110.1 . . ?
H37A C37 H37B 108.4 . . ?
C24A C25 C26 114.7(5) . . ?
C24A C25 H25A 108.6 . . ?
C26 C25 H25A 108.6 . . ?
C24A C25 H25B 108.6 . . ?
C26 C25 H25B 108.6 . . ?
H25A C25 H25B 107.6 . . ?
C34B C29A N30 111.0(5) . . ?
C34B C29A C29 128.0(5) . . ?
N30 C29A C29 120.2(5) . . ?
C33 C34 C34A 118.0(6) . . ?
C33 C34 H34 121.0 . . ?
C34A C34 H34 121.0 . . ?
C34 C33 C32 122.1(6) . . ?
C34 C33 Br2 120.1(5) . . ?
C32 C33 Br2 117.8(5) . . ?
C32 C31 C30A 117.3(6) . . ?
C32 C31 H31 121.3 . . ?
C30A C31 H31 121.3 . . ?
C7 C6 C5 117.3(5) . . ?
C7 C6 H6A 108.0 . . ?
C5 C6 H6A 108.0 . . ?
C7 C6 H6B 108.0 . . ?
C5 C6 H6B 108.0 . . ?
H6A C6 H6B 107.2 . . ?
C4A C14C C1 118.8(6) . . ?
C4A C14C C14B 122.4(5) . . ?
C1 C14C C14B 118.5(6) . . ?
C2 C1 C14C 120.9(6) . . ?
C2 C1 H1 119.6 . . ?
C14C C1 H1 119.6 . . ?
C4A C5 C6 115.4(5) . . ?
C4A C5 H5A 108.4 . . ?
C6 C5 H5A 108.4 . . ?
C4A C5 H5B 108.4 . . ?
C6 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C4 C4A C14C 118.6(6) . . ?
C4 C4A C5 118.6(5) . . ?
C14C C4A C5 122.6(5) . . ?
C3 C4 C4A 121.6(6) . . ?
C3 C4 H4 119.2 . . ?
C4A C4 H4 119.2 . . ?
C3 C2 C1 120.5(6) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.5(6) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
O14 C9 N8 123.3(6) . . ?
O14 C9 C9A 119.7(5) . . ?
N8 C9 C9A 117.0(6) . . ?
C31 C32 C33 121.0(6) . . ?
C31 C32 H32 119.5 . . ?
C33 C32 H32 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C29A N30 C30A C31 -179.0(6) . . . . ?
C35 N30 C30A C31 2.4(10) . . . . ?
C29A N30 C30A C34A 2.1(6) . . . . ?
C35 N30 C30A C34A -176.5(6) . . . . ?
C9A N10 C10A C11 177.4(6) . . . . ?
C9A N10 C10A C14A -1.1(6) . . . . ?
O4 C29 N28 C27 -161.3(6) . . . . ?
C29A C29 N28 C27 20.2(9) . . . . ?
C22 C21 C34C C24A 0.8(9) . . . . ?
C22 C21 C34C C34B -176.5(5) . . . . ?
C34C C21 C22 C23 -1.4(9) . . . . ?
C13 C12 C11 C10A -1.7(8) . . . . ?
N10 C10A C11 C12 179.7(6) . . . . ?
C14A C10A C11 C12 -2.0(9) . . . . ?
C37 O36 C35 N30 71.9(6) . . . . ?
C29A N30 C35 O36 56.1(8) . . . . ?
C30A N30 C35 O36 -125.5(6) . . . . ?
C21 C34C C34B C29A 98.5(8) . . . . ?
C24A C34C C34B C29A -78.7(8) . . . . ?
C21 C34C C34B C34A -70.5(8) . . . . ?
C24A C34C C34B C34A 112.2(7) . . . . ?
C21 C34C C24A C24 0.1(8) . . . . ?
C34B C34C C24A C24 177.3(5) . . . . ?
C21 C34C C24A C25 178.5(5) . . . . ?
C34B C34C C24A C25 -4.3(9) . . . . ?
C31 C30A C34A C34 0.4(9) . . . . ?
N30 C30A C34A C34 179.4(5) . . . . ?
C31 C30A C34A C34B 179.1(5) . . . . ?
N30 C30A C34A C34B -1.9(7) . . . . ?
C29A C34B C34A C34 179.4(6) . . . . ?
C34C C34B C34A C34 -9.8(11) . . . . ?
C29A C34B C34A C30A 0.9(7) . . . . ?
C34C C34B C34A C30A 171.7(6) . . . . ?
C14A C14 C13 C12 -0.3(9) . . . . ?
C14A C14 C13 Br1 178.3(4) . . . . ?
C11 C12 C13 C14 2.9(9) . . . . ?
C11 C12 C13 Br1 -175.8(4) . . . . ?
C13 C14 C14A C10A -3.2(8) . . . . ?
C13 C14 C14A C14B 178.7(6) . . . . ?
N10 C10A C14A C14 -176.9(5) . . . . ?
C11 C10A C14A C14 4.4(9) . . . . ?
N10 C10A C14A C14B 1.7(6) . . . . ?
C11 C10A C14A C14B -177.0(5) . . . . ?
C9A C14B C14A C14 176.6(6) . . . . ?
C14C C14B C14A C14 2.3(11) . . . . ?
C9A C14B C14A C10A -1.6(6) . . . . ?
C14C C14B C14A C10A -175.9(6) . . . . ?
C14A C14B C9A N10 1.0(7) . . . . ?
C14C C14B C9A N10 175.6(5) . . . . ?
C14A C14B C9A C9 -169.7(6) . . . . ?
C14C C14B C9A C9 4.9(10) . . . . ?
C10A N10 C9A C14B 0.0(7) . . . . ?
C10A N10 C9A C9 171.6(5) . . . . ?
C21 C22 C23 C24 1.1(9) . . . . ?
C29 N28 C27 C26 -107.5(7) . . . . ?
C9 N8 C7 C6 103.4(7) . . . . ?
C34C C24A C24 C23 -0.5(9) . . . . ?
C25 C24A C24 C23 -178.9(5) . . . . ?
C22 C23 C24 C24A -0.1(9) . . . . ?
N28 C27 C26 C25 82.8(7) . . . . ?
C35 O36 C37 C38 176.6(5) . . . . ?
C24 C24A C25 C26 -84.4(7) . . . . ?
C34C C24A C25 C26 97.3(7) . . . . ?
C27 C26 C25 C24A -84.6(7) . . . . ?
C34A C34B C29A N30 0.4(7) . . . . ?
C34C C34B C29A N30 -170.5(5) . . . . ?
C34A C34B C29A C29 170.5(6) . . . . ?
C34C C34B C29A C29 -0.5(11) . . . . ?
C30A N30 C29A C34B -1.6(7) . . . . ?
C35 N30 C29A C34B 177.1(5) . . . . ?
C30A N30 C29A C29 -172.5(5) . . . . ?
C35 N30 C29A C29 6.2(9) . . . . ?
O4 C29 C29A C34B -109.3(7) . . . . ?
N28 C29 C29A C34B 69.3(9) . . . . ?
O4 C29 C29A N30 60.0(8) . . . . ?
N28 C29 C29A N30 -121.4(6) . . . . ?
C30A C34A C34 C33 -0.9(9) . . . . ?
C34B C34A C34 C33 -179.3(6) . . . . ?
C34A C34 C33 C32 2.3(9) . . . . ?
C34A C34 C33 Br2 -178.0(4) . . . . ?
N30 C30A C31 C32 -179.9(6) . . . . ?
C34A C30A C31 C32 -1.1(9) . . . . ?
N8 C7 C6 C5 -80.2(6) . . . . ?
C9A C14B C14C C4A 74.1(9) . . . . ?
C14A C14B C14C C4A -112.6(7) . . . . ?
C9A C14B C14C C1 -100.6(8) . . . . ?
C14A C14B C14C C1 72.7(9) . . . . ?
C4A C14C C1 C2 -0.5(10) . . . . ?
C14B C14C C1 C2 174.4(6) . . . . ?
C7 C6 C5 C4A 80.7(6) . . . . ?
C1 C14C C4A C4 0.6(9) . . . . ?
C14B C14C C4A C4 -174.1(6) . . . . ?
C1 C14C C4A C5 -175.9(6) . . . . ?
C14B C14C C4A C5 9.4(9) . . . . ?
C6 C5 C4A C4 85.4(7) . . . . ?
C6 C5 C4A C14C -98.2(7) . . . . ?
C14C C4A C4 C3 0.3(10) . . . . ?
C5 C4A C4 C3 176.9(6) . . . . ?
C14C C1 C2 C3 -0.4(10) . . . . ?
C1 C2 C3 C4 1.2(10) . . . . ?
C4A C4 C3 C2 -1.2(10) . . . . ?
C7 N8 C9 O14 167.0(6) . . . . ?
C7 N8 C9 C9A -15.2(9) . . . . ?
C14B C9A C9 O14 100.7(8) . . . . ?
N10 C9A C9 O14 -69.3(8) . . . . ?
C14B C9A C9 N8 -77.2(8) . . . . ?
N10 C9A C9 N8 112.8(6) . . . . ?
C30A C31 C32 C33 2.3(9) . . . . ?
C34 C33 C32 C31 -3.0(9) . . . . ?
Br2 C33 C32 C31 177.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N10 H10 O4 0.88 1.93 2.773(7) 159.2 .
N28 H28 O14 0.88 2.09 2.826(6) 141.2 2_646
N8 H8 O4 0.88 2.45 3.124(7) 133.3 2_656
C34 H34 Br1 0.95 3.10 3.657(6) 119.3 3_666
C31 H31 O14 0.95 2.64 3.215(7) 119.3 2_656
C6 H6A Br1 0.99 3.07 3.766(6) 128.5 3_666
C32 H32 O14 0.95 2.63 3.228(8) 121.1 2_656

_refine_diff_density_max         0.777
_refine_diff_density_min         -1.160
_refine_diff_density_rms         0.146

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_chwi686
_database_code_depnum_ccdc_archive 'CCDC 2261964'
loop_
_audit_author_name
_audit_author_address
'Vladimir Arion'
;University of Vienna
Austria
;
_audit_update_record             
;
2023-05-10 deposited with the CCDC.	2023-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H20 Br Cl2 Cu N5, H2 O, 2(C3 H7 N O)'
_chemical_formula_sum            'C30 H36 Br Cl2 Cu N7 O3'
_chemical_formula_weight         757.01

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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   17.514(4)
_cell_length_b                   10.420(2)
_cell_length_c                   18.168(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.55(3)
_cell_angle_gamma                90
_cell_volume                     3315.6(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6015
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      63.05

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             1548
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    4.173
_shelx_estimated_absorpt_T_min   0.593
_shelx_estimated_absorpt_T_max   0.759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6374
_exptl_absorpt_correction_T_max  0.7434
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE Stadivari'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            94138
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.868
_diffrn_reflns_theta_max         69.792
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             6172
_reflns_number_gt                5566
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)'
_computing_cell_refinement       'X-Area Recipe 1.36.0.0 (STOE, 2020)'
_computing_data_reduction        
'X-Area Integrate 1.78.3.0; X-Area LANA 1.83.8.0 (STOE, 2020)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0322P)²+3.2386P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6172
_refine_ls_number_parameters     414
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0671
_refine_ls_wR_factor_gt          0.0657
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.43987(8) 0.89215(12) 0.45070(9) 0.03698(19) Uani 0.75 1 d D . P A 1
Br2 Br 0.4418(3) 0.8793(5) 0.4415(3) 0.0842(18) Uani 0.25 1 d D . P A 2
Cu Cu 0.09721(2) 0.15271(2) 0.65780(2) 0.01313(7) Uani 1 1 d . . . . .
Cl1 Cl 0.14113(3) 0.10704(5) 0.77341(2) 0.02030(10) Uani 1 1 d . . . . .
Cl2 Cl -0.03800(2) 0.19867(4) 0.67290(2) 0.01503(9) Uani 1 1 d . . . . .
C1 C 0.38303(11) 0.4441(2) 0.64333(11) 0.0216(4) Uani 1 1 d . . . . .
H1 H 0.4085 0.4481 0.5975 0.026 Uiso 1 1 calc R U . . .
C2 C 0.42169(11) 0.3977(2) 0.70505(12) 0.0261(4) Uani 1 1 d . . . . .
H2 H 0.4731 0.3696 0.7014 0.031 Uiso 1 1 calc R U . . .
C3 C 0.38430(11) 0.3928(2) 0.77208(11) 0.0258(4) Uani 1 1 d . . . . .
H3 H 0.4102 0.3613 0.8145 0.031 Uiso 1 1 calc R U . . .
C4 C 0.30938(11) 0.4338(2) 0.77722(10) 0.0222(4) Uani 1 1 d . . . . .
H4 H 0.2844 0.4299 0.8234 0.027 Uiso 1 1 calc R U . . .
C4A C 0.26982(10) 0.48082(18) 0.71576(10) 0.0172(4) Uani 1 1 d . . . . .
C5 C 0.18884(10) 0.52815(18) 0.72231(10) 0.0178(4) Uani 1 1 d . . . . .
H5A H 0.1796 0.5948 0.6844 0.021 Uiso 1 1 calc R U . . .
H5B H 0.1826 0.5688 0.7711 0.021 Uiso 1 1 calc R U . . .
C6 C 0.12873(10) 0.42211(18) 0.71324(10) 0.0172(4) Uani 1 1 d . . . . .
H6A H 0.1295 0.3695 0.7586 0.021 Uiso 1 1 calc R U . . .
H6B H 0.0780 0.4638 0.7102 0.021 Uiso 1 1 calc R U . . .
N7 N 0.13525(8) 0.33434(15) 0.65002(8) 0.0144(3) Uani 1 1 d . . . . .
C8 C 0.15696(10) 0.36497(17) 0.58473(10) 0.0140(4) Uani 1 1 d . . . . .
C8A C 0.19619(10) 0.48065(17) 0.55783(10) 0.0145(4) Uani 1 1 d . . . . .
N9 N 0.17629(8) 0.53340(15) 0.49106(8) 0.0161(3) Uani 1 1 d . . . . .
H9 H 0.1349 0.5152 0.4653 0.019 Uiso 1 1 calc R U . . .
C9A C 0.23197(10) 0.61937(18) 0.47128(10) 0.0169(4) Uani 1 1 d . . . . .
C10 C 0.23620(11) 0.6987(2) 0.40951(11) 0.0222(4) Uani 1 1 d . . . . .
H10 H 0.1970 0.6990 0.3730 0.027 Uiso 1 1 calc R U . . .
C11 C 0.29946(12) 0.7763(2) 0.40351(12) 0.0268(5) Uani 1 1 d . . . . .
H11 H 0.3048 0.8308 0.3620 0.032 Uiso 1 1 calc R U . . .
C12 C 0.35612(12) 0.7749(2) 0.45885(12) 0.0268(5) Uani 1 1 d D . . . .
C13 C 0.35330(11) 0.6978(2) 0.51974(11) 0.0215(4) Uani 1 1 d . . . . .
H13 H 0.3927 0.6989 0.5560 0.026 Uiso 1 1 calc R U . . .
C13A C 0.28964(10) 0.61693(18) 0.52623(10) 0.0166(4) Uani 1 1 d . . . . .
C13B C 0.26588(10) 0.52735(18) 0.58131(10) 0.0156(4) Uani 1 1 d . . . . .
C13C C 0.30743(10) 0.48461(18) 0.64790(10) 0.0165(4) Uani 1 1 d . . . . .
N14 N 0.14728(8) 0.27671(15) 0.52819(8) 0.0153(3) Uani 1 1 d . . . . .
H14 H 0.1576 0.2933 0.4819 0.018 Uiso 1 1 calc R U . . .
N15 N 0.12001(8) 0.16140(15) 0.55209(8) 0.0141(3) Uani 1 1 d . . . . .
C16 C 0.11414(10) 0.06190(18) 0.51116(9) 0.0146(4) Uani 1 1 d . . . . .
C17 C 0.08657(10) -0.05120(18) 0.55215(10) 0.0141(3) Uani 1 1 d . . . . .
N18 N 0.07889(8) -0.03128(15) 0.62584(8) 0.0142(3) Uani 1 1 d . . . . .
C19 C 0.05467(10) -0.12768(18) 0.66778(10) 0.0165(4) Uani 1 1 d . . . . .
H19 H 0.0498 -0.1140 0.7192 0.020 Uiso 1 1 calc R U . . .
C20 C 0.03627(10) -0.24737(18) 0.63904(10) 0.0178(4) Uani 1 1 d . . . . .
H20 H 0.0191 -0.3143 0.6703 0.021 Uiso 1 1 calc R U . . .
C21 C 0.04330(10) -0.26769(18) 0.56428(10) 0.0183(4) Uani 1 1 d . . . . .
H21 H 0.0303 -0.3484 0.5433 0.022 Uiso 1 1 calc R U . . .
C22 C 0.06969(10) -0.16816(18) 0.52012(10) 0.0170(4) Uani 1 1 d . . . . .
H22 H 0.0760 -0.1805 0.4687 0.020 Uiso 1 1 calc R U . . .
C23 C 0.13408(11) 0.0562(2) 0.43133(10) 0.0206(4) Uani 1 1 d . . . . .
H23A H 0.1335 0.1431 0.4107 0.031 Uiso 1 1 calc R U . . .
H23B H 0.0967 0.0028 0.4051 0.031 Uiso 1 1 calc R U . . .
H23C H 0.1851 0.0191 0.4260 0.031 Uiso 1 1 calc R U . . .
O1 O 0.04601(8) 0.52909(13) 0.39919(7) 0.0209(3) Uani 1 1 d G . . . .
H1A H 0.0394 0.6041 0.3820 0.031 Uiso 1 1 d G U . . .
H1B H 0.0649 0.4868 0.3638 0.031 Uiso 1 1 d G U . . .
O2 O 0.56859(9) 0.31525(19) 0.81966(10) 0.0432(4) Uani 1 1 d . . . . .
C24 C 0.59139(13) 0.4198(3) 0.84140(13) 0.0348(5) Uani 1 1 d . . . . .
H24 H 0.5539 0.4821 0.8533 0.042 Uiso 1 1 calc R U . . .
N24 N 0.66405(11) 0.4534(2) 0.84982(12) 0.0386(5) Uani 1 1 d . . . . .
C25 C 0.68485(19) 0.5803(3) 0.8796(2) 0.0693(10) Uani 1 1 d . . . . .
H25A H 0.6385 0.6314 0.8867 0.104 Uiso 1 1 calc R U . . .
H25B H 0.7185 0.6244 0.8450 0.104 Uiso 1 1 calc R U . . .
H25C H 0.7114 0.5695 0.9270 0.104 Uiso 1 1 calc R U . . .
C26 C 0.72558(14) 0.3652(3) 0.83253(16) 0.0450(7) Uani 1 1 d . . . . .
H26A H 0.7534 0.3427 0.8778 0.067 Uiso 1 1 calc R U . . .
H26B H 0.7606 0.4061 0.7979 0.067 Uiso 1 1 calc R U . . .
H26C H 0.7043 0.2873 0.8102 0.067 Uiso 1 1 calc R U . . .
O3 O 0.27703(8) 0.26121(15) 0.45019(8) 0.0295(3) Uani 1 1 d . . . . .
C27 C 0.29729(11) 0.3352(2) 0.40140(11) 0.0239(4) Uani 1 1 d . . . . .
H27 H 0.2591 0.3674 0.3689 0.029 Uiso 1 1 calc R U . . .
N27 N 0.36832(10) 0.37318(18) 0.39087(10) 0.0292(4) Uani 1 1 d . . . . .
C28 C 0.43017(13) 0.3311(4) 0.43764(15) 0.0543(8) Uani 1 1 d . . . . .
H28A H 0.4107 0.2713 0.4746 0.081 Uiso 1 1 calc R U . . .
H28B H 0.4532 0.4055 0.4623 0.081 Uiso 1 1 calc R U . . .
H28C H 0.4688 0.2880 0.4078 0.081 Uiso 1 1 calc R U . . .
C29 C 0.3864(2) 0.4593(3) 0.3306(2) 0.0733(11) Uani 1 1 d . . . . .
H29A H 0.3406 0.4737 0.3004 0.110 Uiso 1 1 calc R U . . .
H29B H 0.4264 0.4209 0.3003 0.110 Uiso 1 1 calc R U . . .
H29C H 0.4045 0.5414 0.3505 0.110 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 C12 1.916(2) . ?
Br2 C12 1.882(6) . ?
Cu N15 1.9676(15) . ?
Cu N7 2.0120(16) . ?
Cu N18 2.0279(16) . ?
Cu Cl1 2.2802(7) . ?
Cu Cl2 2.4341(7) . ?
C1 C2 1.391(3) . ?
C1 C13C 1.393(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C4A 1.397(3) . ?
C4 H4 0.9500 . ?
C4A C13C 1.404(3) . ?
C4A C5 1.507(3) . ?
C5 C6 1.534(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N7 1.474(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
N7 C8 1.289(2) . ?
C8 N14 1.388(2) . ?
C8 C8A 1.473(2) . ?
C8A N9 1.374(2) . ?
C8A C13B 1.378(2) . ?
N9 C9A 1.375(2) . ?
N9 H9 0.8800 . ?
C9A C10 1.396(3) . ?
C9A C13A 1.414(3) . ?
C10 C11 1.377(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.406(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.369(3) . ?
C13 C13A 1.403(3) . ?
C13 H13 0.9500 . ?
C13A C13B 1.433(3) . ?
C13B C13C 1.475(3) . ?
N14 N15 1.365(2) . ?
N14 H14 0.8800 . ?
N15 C16 1.279(2) . ?
C16 C17 1.478(3) . ?
C16 C23 1.496(2) . ?
C17 N18 1.363(2) . ?
C17 C22 1.381(3) . ?
N18 C19 1.333(2) . ?
C19 C20 1.389(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.381(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.393(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O1 H1A 0.8496 . ?
O1 H1B 0.8493 . ?
O2 C24 1.224(3) . ?
C24 N24 1.327(3) . ?
C24 H24 0.9500 . ?
N24 C26 1.453(3) . ?
N24 C25 1.473(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
O3 C27 1.230(3) . ?
C27 N27 1.321(3) . ?
C27 H27 0.9500 . ?
N27 C28 1.439(3) . ?
N27 C29 1.453(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?

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
N15 Cu N7 79.49(6) . . ?
N15 Cu N18 78.29(6) . . ?
N7 Cu N18 157.05(6) . . ?
N15 Cu Cl1 147.03(5) . . ?
N7 Cu Cl1 98.75(5) . . ?
N18 Cu Cl1 96.75(4) . . ?
N15 Cu Cl2 107.92(5) . . ?
N7 Cu Cl2 98.40(4) . . ?
N18 Cu Cl2 93.83(4) . . ?
Cl1 Cu Cl2 104.91(3) . . ?
C2 C1 C13C 120.86(18) . . ?
C2 C1 H1 119.6 . . ?
C13C C1 H1 119.6 . . ?
C3 C2 C1 119.30(19) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 120.22(19) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C4A 121.16(18) . . ?
C3 C4 H4 119.4 . . ?
C4A C4 H4 119.4 . . ?
C4 C4A C13C 118.59(17) . . ?
C4 C4A C5 120.76(17) . . ?
C13C C4A C5 120.65(16) . . ?
C4A C5 C6 113.65(16) . . ?
C4A C5 H5A 108.8 . . ?
C6 C5 H5A 108.8 . . ?
C4A C5 H5B 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
N7 C6 C5 118.19(15) . . ?
N7 C6 H6A 107.8 . . ?
C5 C6 H6A 107.8 . . ?
N7 C6 H6B 107.8 . . ?
C5 C6 H6B 107.8 . . ?
H6A C6 H6B 107.1 . . ?
C8 N7 C6 126.11(16) . . ?
C8 N7 Cu 113.47(12) . . ?
C6 N7 Cu 120.05(11) . . ?
N7 C8 N14 118.81(16) . . ?
N7 C8 C8A 130.57(17) . . ?
N14 C8 C8A 110.53(15) . . ?
N9 C8A C13B 110.41(16) . . ?
N9 C8A C8 120.33(16) . . ?
C13B C8A C8 126.93(16) . . ?
C8A N9 C9A 108.48(15) . . ?
C8A N9 H9 125.8 . . ?
C9A N9 H9 125.8 . . ?
N9 C9A C10 129.73(17) . . ?
N9 C9A C13A 107.91(16) . . ?
C10 C9A C13A 122.36(17) . . ?
C11 C10 C9A 117.41(18) . . ?
C11 C10 H10 121.3 . . ?
C9A C10 H10 121.3 . . ?
C10 C11 C12 120.01(18) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 123.61(18) . . ?
C13 C12 Br2 120.6(2) . . ?
C11 C12 Br2 115.6(2) . . ?
C13 C12 Br1 118.07(16) . . ?
C11 C12 Br1 118.28(16) . . ?
C12 C13 C13A 117.09(18) . . ?
C12 C13 H13 121.5 . . ?
C13A C13 H13 121.5 . . ?
C13 C13A C9A 119.52(17) . . ?
C13 C13A C13B 133.32(17) . . ?
C9A C13A C13B 107.13(16) . . ?
C8A C13B C13A 106.03(16) . . ?
C8A C13B C13C 125.17(17) . . ?
C13A C13B C13C 128.70(16) . . ?
C1 C13C C4A 119.87(17) . . ?
C1 C13C C13B 120.30(17) . . ?
C4A C13C C13B 119.80(17) . . ?
N15 N14 C8 112.86(14) . . ?
N15 N14 H14 123.6 . . ?
C8 N14 H14 123.6 . . ?
C16 N15 N14 123.69(15) . . ?
C16 N15 Cu 120.93(12) . . ?
N14 N15 Cu 115.20(11) . . ?
N15 C16 C17 112.23(15) . . ?
N15 C16 C23 125.25(17) . . ?
C17 C16 C23 122.50(16) . . ?
N18 C17 C22 121.71(17) . . ?
N18 C17 C16 114.16(16) . . ?
C22 C17 C16 124.13(16) . . ?
C19 N18 C17 118.80(16) . . ?
C19 N18 Cu 126.82(12) . . ?
C17 N18 Cu 114.12(12) . . ?
N18 C19 C20 122.41(17) . . ?
N18 C19 H19 118.8 . . ?
C20 C19 H19 118.8 . . ?
C21 C20 C19 119.01(17) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C20 C21 C22 119.04(17) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C17 C22 C21 119.02(17) . . ?
C17 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C16 C23 H23A 109.5 . . ?
C16 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C16 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
H1A O1 H1B 104.6 . . ?
O2 C24 N24 125.6(2) . . ?
O2 C24 H24 117.2 . . ?
N24 C24 H24 117.2 . . ?
C24 N24 C26 121.3(2) . . ?
C24 N24 C25 120.9(2) . . ?
C26 N24 C25 117.8(2) . . ?
N24 C25 H25A 109.5 . . ?
N24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N24 C26 H26A 109.5 . . ?
N24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O3 C27 N27 124.8(2) . . ?
O3 C27 H27 117.6 . . ?
N27 C27 H27 117.6 . . ?
C27 N27 C28 121.9(2) . . ?
C27 N27 C29 120.5(2) . . ?
C28 N27 C29 117.7(2) . . ?
N27 C28 H28A 109.5 . . ?
N27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N27 C29 H29A 109.5 . . ?
N27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
C13C C1 C2 C3 -0.5(3) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C4A -0.1(3) . . . . ?
C3 C4 C4A C13C 0.6(3) . . . . ?
C3 C4 C4A C5 -178.54(19) . . . . ?
C4 C4A C5 C6 -87.3(2) . . . . ?
C13C C4A C5 C6 93.6(2) . . . . ?
C4A C5 C6 N7 -48.6(2) . . . . ?
C5 C6 N7 C8 -37.3(3) . . . . ?
C5 C6 N7 Cu 150.03(13) . . . . ?
C6 N7 C8 N14 -168.76(16) . . . . ?
Cu N7 C8 N14 4.3(2) . . . . ?
C6 N7 C8 C8A 15.1(3) . . . . ?
Cu N7 C8 C8A -171.89(15) . . . . ?
N7 C8 C8A N9 -140.9(2) . . . . ?
N14 C8 C8A N9 42.7(2) . . . . ?
N7 C8 C8A C13B 58.2(3) . . . . ?
N14 C8 C8A C13B -118.2(2) . . . . ?
C13B C8A N9 C9A -2.2(2) . . . . ?
C8 C8A N9 C9A -165.99(16) . . . . ?
C8A N9 C9A C10 -178.1(2) . . . . ?
C8A N9 C9A C13A 2.0(2) . . . . ?
N9 C9A C10 C11 -180.0(2) . . . . ?
C13A C9A C10 C11 -0.1(3) . . . . ?
C9A C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 C13 1.1(4) . . . . ?
C10 C11 C12 Br2 177.0(3) . . . . ?
C10 C11 C12 Br1 -176.34(18) . . . . ?
C11 C12 C13 C13A -0.3(3) . . . . ?
Br2 C12 C13 C13A -176.0(3) . . . . ?
Br1 C12 C13 C13A 177.12(16) . . . . ?
C12 C13 C13A C9A -0.7(3) . . . . ?
C12 C13 C13A C13B -178.2(2) . . . . ?
N9 C9A C13A C13 -179.25(17) . . . . ?
C10 C9A C13A C13 0.9(3) . . . . ?
N9 C9A C13A C13B -1.2(2) . . . . ?
C10 C9A C13A C13B 178.96(18) . . . . ?
N9 C8A C13B C13A 1.4(2) . . . . ?
C8 C8A C13B C13A 163.89(17) . . . . ?
N9 C8A C13B C13C -175.26(17) . . . . ?
C8 C8A C13B C13C -12.8(3) . . . . ?
C13 C13A C13B C8A 177.6(2) . . . . ?
C9A C13A C13B C8A -0.1(2) . . . . ?
C13 C13A C13B C13C -5.9(4) . . . . ?
C9A C13A C13B C13C 176.36(18) . . . . ?
C2 C1 C13C C4A 1.0(3) . . . . ?
C2 C1 C13C C13B -176.87(19) . . . . ?
C4 C4A C13C C1 -1.1(3) . . . . ?
C5 C4A C13C C1 178.07(17) . . . . ?
C4 C4A C13C C13B 176.81(18) . . . . ?
C5 C4A C13C C13B -4.0(3) . . . . ?
C8A C13B C13C C1 126.9(2) . . . . ?
C13A C13B C13C C1 -49.0(3) . . . . ?
C8A C13B C13C C4A -51.0(3) . . . . ?
C13A C13B C13C C4A 133.1(2) . . . . ?
N7 C8 N14 N15 -4.7(2) . . . . ?
C8A C8 N14 N15 172.19(14) . . . . ?
C8 N14 N15 C16 -172.51(16) . . . . ?
C8 N14 N15 Cu 2.75(18) . . . . ?
N14 N15 C16 C17 177.14(15) . . . . ?
Cu N15 C16 C17 2.1(2) . . . . ?
N14 N15 C16 C23 -1.5(3) . . . . ?
Cu N15 C16 C23 -176.51(14) . . . . ?
N15 C16 C17 N18 -5.2(2) . . . . ?
C23 C16 C17 N18 173.52(16) . . . . ?
N15 C16 C17 C22 174.91(17) . . . . ?
C23 C16 C17 C22 -6.4(3) . . . . ?
C22 C17 N18 C19 0.2(3) . . . . ?
C16 C17 N18 C19 -179.70(15) . . . . ?
C22 C17 N18 Cu -174.32(13) . . . . ?
C16 C17 N18 Cu 5.76(18) . . . . ?
C17 N18 C19 C20 -0.6(3) . . . . ?
Cu N18 C19 C20 173.14(13) . . . . ?
N18 C19 C20 C21 0.0(3) . . . . ?
C19 C20 C21 C22 0.9(3) . . . . ?
N18 C17 C22 C21 0.8(3) . . . . ?
C16 C17 C22 C21 -179.33(17) . . . . ?
C20 C21 C22 C17 -1.3(3) . . . . ?
O2 C24 N24 C26 0.6(4) . . . . ?
O2 C24 N24 C25 -177.2(3) . . . . ?
O3 C27 N27 C28 -0.8(4) . . . . ?
O3 C27 N27 C29 178.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6A Cl1 0.99 2.76 3.466(2) 129.1 .
N9 H9 O1 0.88 1.96 2.814(2) 162.7 .
C13 H13 O2 0.95 2.65 3.436(3) 141.0 2_656
N14 H14 O3 0.88 2.20 2.694(2) 115.2 .
C19 H19 Cl1 0.95 2.97 3.450(2) 112.9 .
C19 H19 Cl2 0.95 2.78 3.4284(19) 126.7 2_546
C20 H20 Cl2 0.95 2.87 3.463(2) 121.7 2_546
C22 H22 Cl2 0.95 2.66 3.559(2) 158.5 3_556
C23 H23B Cl2 0.98 2.73 3.662(2) 159.5 3_556
O1 H1A Cl2 0.85 2.28 3.1272(15) 171.7 3_566
O1 H1B Cl1 0.85 2.34 3.1752(16) 167.8 4_565
C24 H24 Br1 0.95 2.98 3.863(3) 154.5 4_576
C24 H24 Br2 0.95 2.93 3.827(6) 158.5 4_576
C27 H27 Cl1 0.95 2.70 3.623(2) 164.9 4_565
C28 H28C O2 0.98 2.61 3.591(3) 175.4 4_565

_refine_diff_density_max         0.630
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.053

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_chwi1101
_database_code_depnum_ccdc_archive 'CCDC 2261965'
loop_
_audit_author_name
_audit_author_address
'Vladimir Arion'
;University of Vienna
Austria
;
_audit_update_record             
;
2023-05-10 deposited with the CCDC.	2023-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 Br N5, C H2 Cl2'
_chemical_formula_sum            'C26 H24 Br Cl2 N5'
_chemical_formula_weight         557.31

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.5481(7)
_cell_length_b                   11.5707(7)
_cell_length_c                   20.2679(13)
_cell_angle_alpha                79.717(5)
_cell_angle_beta                 89.452(5)
_cell_angle_gamma                64.211(4)
_cell_volume                     2392.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    56364
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      30.47

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.085
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.968
_shelx_estimated_absorpt_T_min   0.851
_shelx_estimated_absorpt_T_max   0.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7075
_exptl_absorpt_correction_T_max  0.9712
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            58355
_diffrn_reflns_av_unetI/netI     0.0617
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.760
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             8435
_reflns_number_gt                5827
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)'
_computing_cell_refinement       'X-Area Recipe 1.36.0-0 (STOE, 2020)'
_computing_data_reduction        
'X-Area Integrate 1.78.3.0; X-Area LANA 1.83.8.0 (STOE, 2020)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1139P)²+1.4784P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8435
_refine_ls_number_parameters     615
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1795
_refine_ls_wR_factor_gt          0.1586
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 -0.03236(5) 0.69326(5) 0.25264(3) 0.01956(18) Uani 1 1 d . . . . .
Br2 Br 0.13693(5) 0.30625(5) 0.24384(3) 0.02002(18) Uani 1 1 d . . . . .
Cl4 Cl 1.17596(15) 0.04358(18) 0.63485(8) 0.0410(4) Uani 1 1 d . . . . .
Cl3 Cl 0.93051(14) 0.09686(17) 0.57009(9) 0.0377(4) Uani 1 1 d . . . . .
Cl2 Cl 0.4286(2) 1.0782(2) 0.07886(13) 0.0805(8) Uani 1 1 d . . . . .
Cl1 Cl 0.2699(2) 0.98475(18) 0.15880(10) 0.0562(6) Uani 1 1 d . . . . .
N19 N 1.1345(4) 0.2793(4) 0.4534(2) 0.0208(11) Uani 1 1 d . . . . .
N16 N 0.8408(4) 0.5229(4) 0.3659(2) 0.0156(10) Uani 1 1 d . . . . .
N15 N 0.7269(4) 0.5335(4) 0.3362(2) 0.0155(10) Uani 1 1 d . . . . .
N10 N 0.4986(4) 0.6572(4) 0.2293(2) 0.0154(10) Uani 1 1 d . . . . .
H10 H 0.5558 0.6350 0.1992 0.018 Uiso 1 1 calc R U . . .
N8 N 0.6673(4) 0.7583(4) 0.3278(2) 0.0190(10) Uani 1 1 d . . . . .
H8 H 0.7314 0.7409 0.3569 0.023 Uiso 1 1 calc R U . . .
N49 N 0.9309(4) 0.7562(5) 0.0509(3) 0.0273(12) Uani 1 1 d . . . . .
N46 N 0.8466(4) 0.5084(4) 0.1302(2) 0.0143(10) Uani 1 1 d . . . . .
N45 N 0.7430(4) 0.4950(4) 0.1613(2) 0.0129(9) Uani 1 1 d . . . . .
N40 N 0.6215(4) 0.3683(4) 0.2704(2) 0.0139(10) Uani 1 1 d . . . . .
H40 H 0.6554 0.3937 0.3003 0.017 Uiso 1 1 calc R U . . .
N38 N 0.8843(4) 0.2709(4) 0.1726(2) 0.0169(10) Uani 1 1 d . . . . .
H38 H 0.9330 0.2885 0.1426 0.020 Uiso 1 1 calc R U . . .
C18 C 1.0454(5) 0.4002(5) 0.4229(3) 0.0138(11) Uani 1 1 d . . . . .
C20 C 1.2384(5) 0.2730(5) 0.4865(3) 0.0230(13) Uani 1 1 d . . . . .
H20 H 1.3012 0.1893 0.5083 0.028 Uiso 1 1 calc R U . . .
C21 C 1.2591(5) 0.3790(5) 0.4906(3) 0.0188(12) Uani 1 1 d . . . . .
H21 H 1.3346 0.3690 0.5142 0.023 Uiso 1 1 calc R U . . .
C22 C 1.1661(5) 0.5031(5) 0.4590(3) 0.0185(12) Uani 1 1 d . . . . .
H22 H 1.1769 0.5793 0.4609 0.022 Uiso 1 1 calc R U . . .
C23 C 1.0596(5) 0.5118(5) 0.4256(3) 0.0168(12) Uani 1 1 d . . . . .
H23 H 0.9952 0.5949 0.4041 0.020 Uiso 1 1 calc R U . . .
C17 C 0.9296(5) 0.4059(5) 0.3876(3) 0.0153(12) Uani 1 1 d . . . . .
C9 C 0.6451(5) 0.6583(5) 0.3182(3) 0.0159(12) Uani 1 1 d . . . . .
C9A C 0.5170(5) 0.6865(5) 0.2908(3) 0.0169(12) Uani 1 1 d . . . . .
C14B C 0.4055(5) 0.7248(5) 0.3224(3) 0.0155(12) Uani 1 1 d . . . . .
C14A C 0.3137(5) 0.7107(5) 0.2804(3) 0.0137(11) Uani 1 1 d . . . . .
C10A C 0.3753(5) 0.6688(5) 0.2236(3) 0.0152(12) Uani 1 1 d . . . . .
C24 C 0.9225(5) 0.2817(5) 0.3823(3) 0.0226(13) Uani 1 1 d . . . . .
H24A H 0.8824 0.2914 0.3379 0.034 Uiso 1 1 calc R U . . .
H24B H 0.8707 0.2629 0.4173 0.034 Uiso 1 1 calc R U . . .
H24C H 1.0097 0.2096 0.3880 0.034 Uiso 1 1 calc R U . . .
C7 C 0.5928(5) 0.8956(5) 0.2935(3) 0.0221(13) Uani 1 1 d . . . . .
H7A H 0.5374 0.8985 0.2556 0.027 Uiso 1 1 calc R U . . .
H7B H 0.6536 0.9297 0.2744 0.027 Uiso 1 1 calc R U . . .
C6 C 0.5072(5) 0.9858(5) 0.3396(3) 0.0236(13) Uani 1 1 d . . . . .
H6A H 0.5570 0.9633 0.3833 0.028 Uiso 1 1 calc R U . . .
H6B H 0.4887 1.0770 0.3192 0.028 Uiso 1 1 calc R U . . .
C5 C 0.3793(5) 0.9802(5) 0.3530(3) 0.0196(13) Uani 1 1 d . . . . .
H5A H 0.3192 1.0630 0.3661 0.024 Uiso 1 1 calc R U . . .
H5B H 0.3418 0.9751 0.3105 0.024 Uiso 1 1 calc R U . . .
C4A C 0.3873(5) 0.8681(5) 0.4064(3) 0.0179(12) Uani 1 1 d . . . . .
C4 C 0.3824(5) 0.8817(5) 0.4734(3) 0.0188(12) Uani 1 1 d . . . . .
H4 H 0.3809 0.9588 0.4844 0.023 Uiso 1 1 calc R U . . .
C3 C 0.3796(5) 0.7866(5) 0.5245(3) 0.0226(13) Uani 1 1 d . . . . .
H3 H 0.3770 0.7984 0.5698 0.027 Uiso 1 1 calc R U . . .
C2 C 0.3806(5) 0.6741(5) 0.5094(3) 0.0179(12) Uani 1 1 d . . . . .
H2 H 0.3765 0.6090 0.5440 0.022 Uiso 1 1 calc R U . . .
C1 C 0.3876(5) 0.6581(5) 0.4438(3) 0.0147(11) Uani 1 1 d . . . . .
H1 H 0.3892 0.5804 0.4337 0.018 Uiso 1 1 calc R U . . .
C14C C 0.3923(5) 0.7519(5) 0.3915(3) 0.0154(12) Uani 1 1 d . . . . .
C14 C 0.1894(5) 0.7221(5) 0.2893(3) 0.0130(11) Uani 1 1 d . . . . .
H14 H 0.1459 0.7516 0.3274 0.016 Uiso 1 1 calc R U . . .
C13 C 0.1317(5) 0.6896(5) 0.2413(3) 0.0142(11) Uani 1 1 d . . . . .
C12 C 0.1934(5) 0.6496(5) 0.1842(3) 0.0162(12) Uani 1 1 d . . . . .
H12 H 0.1504 0.6290 0.1517 0.019 Uiso 1 1 calc R U . . .
C11 C 0.3161(5) 0.6392(5) 0.1740(3) 0.0155(12) Uani 1 1 d . . . . .
H11 H 0.3579 0.6131 0.1350 0.019 Uiso 1 1 calc R U . . .
C48 C 0.9436(5) 0.6347(5) 0.0742(3) 0.0153(12) Uani 1 1 d . . . . .
C50 C 1.0306(6) 0.7651(6) 0.0190(3) 0.0312(15) Uani 1 1 d . . . . .
H50 H 1.0239 0.8501 0.0025 0.037 Uiso 1 1 calc R U . . .
C51 C 1.1416(6) 0.6595(6) 0.0087(3) 0.0274(14) Uani 1 1 d . . . . .
H51 H 1.2084 0.6719 -0.0145 0.033 Uiso 1 1 calc R U . . .
C52 C 1.1532(5) 0.5344(6) 0.0331(3) 0.0222(13) Uani 1 1 d . . . . .
H52 H 1.2279 0.4590 0.0271 0.027 Uiso 1 1 calc R U . . .
C53 C 1.0531(5) 0.5236(5) 0.0664(3) 0.0182(12) Uani 1 1 d . . . . .
H53 H 1.0587 0.4394 0.0841 0.022 Uiso 1 1 calc R U . . .
C47 C 0.8322(5) 0.6250(5) 0.1092(3) 0.0153(12) Uani 1 1 d . . . . .
C39 C 0.7731(5) 0.3703(5) 0.1813(3) 0.0151(12) Uani 1 1 d . . . . .
C39A C 0.6698(5) 0.3393(5) 0.2102(3) 0.0151(12) Uani 1 1 d . . . . .
C44B C 0.5963(5) 0.2970(5) 0.1773(3) 0.0138(11) Uani 1 1 d . . . . .
C44A C 0.4931(5) 0.3075(5) 0.2191(3) 0.0134(11) Uani 1 1 d . . . . .
C40A C 0.5117(5) 0.3510(5) 0.2760(3) 0.0139(11) Uani 1 1 d . . . . .
C54 C 0.7146(5) 0.7468(5) 0.1157(3) 0.0231(13) Uani 1 1 d . . . . .
H54A H 0.7271 0.8236 0.0954 0.035 Uiso 1 1 calc R U . . .
H54B H 0.7003 0.7476 0.1633 0.035 Uiso 1 1 calc R U . . .
H54C H 0.6395 0.7487 0.0925 0.035 Uiso 1 1 calc R U . . .
C37 C 0.9324(5) 0.1345(5) 0.2086(3) 0.0239(13) Uani 1 1 d . . . . .
H37A H 0.8791 0.1322 0.2470 0.029 Uiso 1 1 calc R U . . .
H37B H 1.0218 0.1045 0.2274 0.029 Uiso 1 1 calc R U . . .
C36 C 0.9316(5) 0.0383(5) 0.1666(3) 0.0244(14) Uani 1 1 d . . . . .
H36A H 0.9945 -0.0509 0.1885 0.029 Uiso 1 1 calc R U . . .
H36B H 0.9614 0.0587 0.1220 0.029 Uiso 1 1 calc R U . . .
C35 C 0.7990(5) 0.0381(5) 0.1560(3) 0.0219(13) Uani 1 1 d . . . . .
H35A H 0.8144 -0.0489 0.1475 0.026 Uiso 1 1 calc R U . . .
H35B H 0.7559 0.0490 0.1984 0.026 Uiso 1 1 calc R U . . .
C34A C 0.7073(5) 0.1410(5) 0.0997(3) 0.0148(12) Uani 1 1 d . . . . .
C34 C 0.7113(5) 0.1142(5) 0.0348(3) 0.0213(13) Uani 1 1 d . . . . .
H34 H 0.7761 0.0338 0.0264 0.026 Uiso 1 1 calc R U . . .
C33 C 0.6241(5) 0.2008(5) -0.0172(3) 0.0217(13) Uani 1 1 d . . . . .
H33 H 0.6285 0.1791 -0.0605 0.026 Uiso 1 1 calc R U . . .
C32 C 0.5301(5) 0.3192(5) -0.0067(3) 0.0194(12) Uani 1 1 d . . . . .
H32 H 0.4711 0.3801 -0.0427 0.023 Uiso 1 1 calc R U . . .
C31 C 0.5230(5) 0.3480(5) 0.0569(3) 0.0162(12) Uani 1 1 d . . . . .
H31 H 0.4566 0.4282 0.0644 0.019 Uiso 1 1 calc R U . . .
C44C C 0.6106(5) 0.2625(5) 0.1102(3) 0.0140(11) Uani 1 1 d . . . . .
C44 C 0.3818(5) 0.2900(5) 0.2092(3) 0.0158(12) Uani 1 1 d . . . . .
H44 H 0.3686 0.2596 0.1707 0.019 Uiso 1 1 calc R U . . .
C43 C 0.2936(5) 0.3177(5) 0.2561(3) 0.0146(11) Uani 1 1 d . . . . .
C42 C 0.3126(5) 0.3608(5) 0.3143(3) 0.0151(12) Uani 1 1 d . . . . .
H42 H 0.2497 0.3789 0.3464 0.018 Uiso 1 1 calc R U . . .
C41 C 0.4231(5) 0.3766(5) 0.3247(3) 0.0148(11) Uani 1 1 d . . . . .
H41 H 0.4377 0.4041 0.3639 0.018 Uiso 1 1 calc R U . . .
C62 C 1.0958(5) 0.0438(6) 0.5612(3) 0.0235(13) Uani 1 1 d . . . . .
H62A H 1.1085 0.1023 0.5229 0.028 Uiso 1 1 calc R U . . .
H62B H 1.1335 -0.0456 0.5514 0.028 Uiso 1 1 calc R U . . .
C61 C 0.2625(8) 1.1113(6) 0.0954(3) 0.058(2) Uani 1 1 d . . . . .
H61A H 0.2179 1.1963 0.1100 0.070 Uiso 1 1 calc R U . . .
H61B H 0.2148 1.1144 0.0543 0.070 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 C13 1.889(5) . ?
Br2 C43 1.892(5) . ?
Cl4 C62 1.762(5) . ?
Cl3 C62 1.751(6) . ?
Cl2 C61 1.826(9) . ?
Cl1 C61 1.739(7) . ?
N19 C20 1.347(7) . ?
N19 C18 1.360(6) . ?
N16 C17 1.291(6) . ?
N16 N15 1.399(5) . ?
N15 C9 1.320(6) . ?
N10 C10A 1.374(6) . ?
N10 C9A 1.391(7) . ?
N10 H10 0.8800 . ?
N8 C9 1.334(7) . ?
N8 C7 1.475(6) . ?
N8 H8 0.8800 . ?
N49 C48 1.343(7) . ?
N49 C50 1.349(7) . ?
N46 C47 1.277(6) . ?
N46 N45 1.401(6) . ?
N45 C39 1.313(6) . ?
N40 C39A 1.372(7) . ?
N40 C40A 1.369(6) . ?
N40 H40 0.8800 . ?
N38 C39 1.337(6) . ?
N38 C37 1.472(6) . ?
N38 H38 0.8800 . ?
C18 C23 1.381(7) . ?
C18 C17 1.493(7) . ?
C20 C21 1.365(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.403(7) . ?
C21 H21 0.9500 . ?
C22 C23 1.366(7) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C17 C24 1.497(7) . ?
C9 C9A 1.461(7) . ?
C9A C14B 1.362(7) . ?
C14B C14A 1.447(7) . ?
C14B C14C 1.481(7) . ?
C14A C14 1.395(7) . ?
C14A C10A 1.397(8) . ?
C10A C11 1.390(7) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C7 C6 1.539(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C6 C5 1.526(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C5 C4A 1.503(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C4A C4 1.393(7) . ?
C4A C14C 1.407(7) . ?
C4 C3 1.380(8) . ?
C4 H4 0.9500 . ?
C3 C2 1.384(7) . ?
C3 H3 0.9500 . ?
C2 C1 1.371(7) . ?
C2 H2 0.9500 . ?
C1 C14C 1.395(7) . ?
C1 H1 0.9500 . ?
C14 C13 1.377(7) . ?
C14 H14 0.9500 . ?
C13 C12 1.397(7) . ?
C12 C11 1.385(7) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
C48 C53 1.390(7) . ?
C48 C47 1.500(7) . ?
C50 C51 1.379(8) . ?
C50 H50 0.9500 . ?
C51 C52 1.391(8) . ?
C51 H51 0.9500 . ?
C52 C53 1.374(7) . ?
C52 H52 0.9500 . ?
C53 H53 0.9500 . ?
C47 C54 1.498(7) . ?
C39 C39A 1.476(7) . ?
C39A C44B 1.376(7) . ?
C44B C44A 1.430(7) . ?
C44B C44C 1.472(7) . ?
C44A C40A 1.391(7) . ?
C44A C44 1.406(7) . ?
C40A C41 1.389(7) . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C37 C36 1.520(7) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C36 C35 1.549(7) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C35 C34A 1.511(7) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C34A C34 1.400(7) . ?
C34A C44C 1.416(7) . ?
C34 C33 1.376(8) . ?
C34 H34 0.9500 . ?
C33 C32 1.381(7) . ?
C33 H33 0.9500 . ?
C32 C31 1.380(7) . ?
C32 H32 0.9500 . ?
C31 C44C 1.393(7) . ?
C31 H31 0.9500 . ?
C44 C43 1.360(7) . ?
C44 H44 0.9500 . ?
C43 C42 1.414(7) . ?
C42 C41 1.388(7) . ?
C42 H42 0.9500 . ?
C41 H41 0.9500 . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?

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
C20 N19 C18 116.8(5) . . ?
C17 N16 N15 116.5(4) . . ?
C9 N15 N16 109.3(4) . . ?
C10A N10 C9A 108.0(4) . . ?
C10A N10 H10 126.0 . . ?
C9A N10 H10 126.0 . . ?
C9 N8 C7 125.2(4) . . ?
C9 N8 H8 117.4 . . ?
C7 N8 H8 117.4 . . ?
C48 N49 C50 116.4(5) . . ?
C47 N46 N45 116.6(4) . . ?
C39 N45 N46 109.5(4) . . ?
C39A N40 C40A 108.3(4) . . ?
C39A N40 H40 125.9 . . ?
C40A N40 H40 125.9 . . ?
C39 N38 C37 125.7(5) . . ?
C39 N38 H38 117.2 . . ?
C37 N38 H38 117.2 . . ?
N19 C18 C23 122.0(5) . . ?
N19 C18 C17 116.2(4) . . ?
C23 C18 C17 121.8(5) . . ?
N19 C20 C21 124.3(5) . . ?
N19 C20 H20 117.9 . . ?
C21 C20 H20 117.9 . . ?
C20 C21 C22 118.3(5) . . ?
C20 C21 H21 120.9 . . ?
C22 C21 H21 120.9 . . ?
C23 C22 C21 118.4(5) . . ?
C23 C22 H22 120.8 . . ?
C21 C22 H22 120.8 . . ?
C22 C23 C18 120.2(5) . . ?
C22 C23 H23 119.9 . . ?
C18 C23 H23 119.9 . . ?
N16 C17 C18 114.2(4) . . ?
N16 C17 C24 125.9(5) . . ?
C18 C17 C24 119.8(4) . . ?
N15 C9 N8 125.2(5) . . ?
N15 C9 C9A 116.3(5) . . ?
N8 C9 C9A 118.3(5) . . ?
C14B C9A N10 110.1(5) . . ?
C14B C9A C9 127.7(5) . . ?
N10 C9A C9 121.6(4) . . ?
C9A C14B C14A 106.3(5) . . ?
C9A C14B C14C 125.0(5) . . ?
C14A C14B C14C 127.9(5) . . ?
C14 C14A C10A 120.0(5) . . ?
C14 C14A C14B 132.8(5) . . ?
C10A C14A C14B 107.0(4) . . ?
N10 C10A C11 129.3(5) . . ?
N10 C10A C14A 108.5(4) . . ?
C11 C10A C14A 122.1(5) . . ?
C17 C24 H24A 109.5 . . ?
C17 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C17 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N8 C7 C6 113.9(5) . . ?
N8 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
N8 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C5 C6 C7 115.9(5) . . ?
C5 C6 H6A 108.3 . . ?
C7 C6 H6A 108.3 . . ?
C5 C6 H6B 108.3 . . ?
C7 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
C4A C5 C6 115.4(4) . . ?
C4A C5 H5A 108.4 . . ?
C6 C5 H5A 108.4 . . ?
C4A C5 H5B 108.4 . . ?
C6 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C4 C4A C14C 118.0(5) . . ?
C4 C4A C5 119.1(5) . . ?
C14C C4A C5 122.8(5) . . ?
C3 C4 C4A 122.0(5) . . ?
C3 C4 H4 119.0 . . ?
C4A C4 H4 119.0 . . ?
C4 C3 C2 119.8(5) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C1 C2 C3 119.0(5) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C1 C14C 122.3(5) . . ?
C2 C1 H1 118.8 . . ?
C14C C1 H1 118.8 . . ?
C1 C14C C4A 118.8(5) . . ?
C1 C14C C14B 119.0(5) . . ?
C4A C14C C14B 122.1(5) . . ?
C13 C14 C14A 118.1(5) . . ?
C13 C14 H14 120.9 . . ?
C14A C14 H14 120.9 . . ?
C14 C13 C12 121.4(5) . . ?
C14 C13 Br1 120.4(4) . . ?
C12 C13 Br1 118.2(4) . . ?
C11 C12 C13 121.3(5) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C11 C10A 117.0(5) . . ?
C12 C11 H11 121.5 . . ?
C10A C11 H11 121.5 . . ?
N49 C48 C53 122.3(5) . . ?
N49 C48 C47 116.3(4) . . ?
C53 C48 C47 121.4(5) . . ?
N49 C50 C51 124.6(6) . . ?
N49 C50 H50 117.7 . . ?
C51 C50 H50 117.7 . . ?
C50 C51 C52 118.4(6) . . ?
C50 C51 H51 120.8 . . ?
C52 C51 H51 120.8 . . ?
C53 C52 C51 117.8(5) . . ?
C53 C52 H52 121.1 . . ?
C51 C52 H52 121.1 . . ?
C52 C53 C48 120.6(5) . . ?
C52 C53 H53 119.7 . . ?
C48 C53 H53 119.7 . . ?
N46 C47 C54 125.2(5) . . ?
N46 C47 C48 114.9(4) . . ?
C54 C47 C48 120.0(4) . . ?
N45 C39 N38 125.6(5) . . ?
N45 C39 C39A 116.2(4) . . ?
N38 C39 C39A 118.0(5) . . ?
N40 C39A C44B 110.5(5) . . ?
N40 C39A C39 123.3(4) . . ?
C44B C39A C39 125.5(5) . . ?
C39A C44B C44A 105.0(5) . . ?
C39A C44B C44C 128.1(5) . . ?
C44A C44B C44C 126.6(5) . . ?
C40A C44A C44 120.2(5) . . ?
C40A C44A C44B 108.2(4) . . ?
C44 C44A C44B 131.5(5) . . ?
N40 C40A C41 130.5(5) . . ?
N40 C40A C44A 107.9(4) . . ?
C41 C40A C44A 121.5(5) . . ?
C47 C54 H54A 109.5 . . ?
C47 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C47 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
N38 C37 C36 115.3(5) . . ?
N38 C37 H37A 108.5 . . ?
C36 C37 H37A 108.5 . . ?
N38 C37 H37B 108.5 . . ?
C36 C37 H37B 108.5 . . ?
H37A C37 H37B 107.5 . . ?
C37 C36 C35 115.0(5) . . ?
C37 C36 H36A 108.5 . . ?
C35 C36 H36A 108.5 . . ?
C37 C36 H36B 108.5 . . ?
C35 C36 H36B 108.5 . . ?
H36A C36 H36B 107.5 . . ?
C34A C35 C36 116.5(5) . . ?
C34A C35 H35A 108.2 . . ?
C36 C35 H35A 108.2 . . ?
C34A C35 H35B 108.2 . . ?
C36 C35 H35B 108.2 . . ?
H35A C35 H35B 107.3 . . ?
C34 C34A C44C 117.6(5) . . ?
C34 C34A C35 119.7(5) . . ?
C44C C34A C35 122.7(5) . . ?
C33 C34 C34A 122.0(5) . . ?
C33 C34 H34 119.0 . . ?
C34A C34 H34 119.0 . . ?
C34 C33 C32 120.2(5) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C31 C32 C33 119.2(5) . . ?
C31 C32 H32 120.4 . . ?
C33 C32 H32 120.4 . . ?
C32 C31 C44C 121.7(5) . . ?
C32 C31 H31 119.1 . . ?
C44C C31 H31 119.1 . . ?
C31 C44C C34A 119.3(5) . . ?
C31 C44C C44B 119.3(4) . . ?
C34A C44C C44B 121.3(5) . . ?
C43 C44 C44A 118.3(5) . . ?
C43 C44 H44 120.8 . . ?
C44A C44 H44 120.8 . . ?
C44 C43 C42 121.7(5) . . ?
C44 C43 Br2 120.9(4) . . ?
C42 C43 Br2 117.4(4) . . ?
C41 C42 C43 120.1(5) . . ?
C41 C42 H42 119.9 . . ?
C43 C42 H42 119.9 . . ?
C42 C41 C40A 118.1(5) . . ?
C42 C41 H41 121.0 . . ?
C40A C41 H41 121.0 . . ?
Cl3 C62 Cl4 111.2(3) . . ?
Cl3 C62 H62A 109.4 . . ?
Cl4 C62 H62A 109.4 . . ?
Cl3 C62 H62B 109.4 . . ?
Cl4 C62 H62B 109.4 . . ?
H62A C62 H62B 108.0 . . ?
Cl1 C61 Cl2 106.9(4) . . ?
Cl1 C61 H61A 110.3 . . ?
Cl2 C61 H61A 110.3 . . ?
Cl1 C61 H61B 110.3 . . ?
Cl2 C61 H61B 110.3 . . ?
H61A C61 H61B 108.6 . . ?

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
C17 N16 N15 C9 178.6(5) . . . . ?
C47 N46 N45 C39 -178.8(4) . . . . ?
C20 N19 C18 C23 -0.2(8) . . . . ?
C20 N19 C18 C17 -178.8(5) . . . . ?
C18 N19 C20 C21 -0.5(8) . . . . ?
N19 C20 C21 C22 0.7(9) . . . . ?
C20 C21 C22 C23 -0.2(8) . . . . ?
C21 C22 C23 C18 -0.4(8) . . . . ?
N19 C18 C23 C22 0.6(8) . . . . ?
C17 C18 C23 C22 179.2(5) . . . . ?
N15 N16 C17 C18 -176.0(4) . . . . ?
N15 N16 C17 C24 1.6(8) . . . . ?
N19 C18 C17 N16 172.6(5) . . . . ?
C23 C18 C17 N16 -6.1(7) . . . . ?
N19 C18 C17 C24 -5.2(7) . . . . ?
C23 C18 C17 C24 176.1(5) . . . . ?
N16 N15 C9 N8 -1.0(7) . . . . ?
N16 N15 C9 C9A -175.6(4) . . . . ?
C7 N8 C9 N15 163.6(5) . . . . ?
C7 N8 C9 C9A -21.9(8) . . . . ?
C10A N10 C9A C14B -3.9(6) . . . . ?
C10A N10 C9A C9 167.6(5) . . . . ?
N15 C9 C9A C14B 102.6(6) . . . . ?
N8 C9 C9A C14B -72.3(8) . . . . ?
N15 C9 C9A N10 -67.4(7) . . . . ?
N8 C9 C9A N10 117.7(6) . . . . ?
N10 C9A C14B C14A 3.8(6) . . . . ?
C9 C9A C14B C14A -167.1(5) . . . . ?
N10 C9A C14B C14C 174.2(5) . . . . ?
C9 C9A C14B C14C 3.3(9) . . . . ?
C9A C14B C14A C14 172.7(5) . . . . ?
C14C C14B C14A C14 2.7(9) . . . . ?
C9A C14B C14A C10A -2.3(6) . . . . ?
C14C C14B C14A C10A -172.3(5) . . . . ?
C9A N10 C10A C11 -174.2(5) . . . . ?
C9A N10 C10A C14A 2.4(5) . . . . ?
C14 C14A C10A N10 -175.8(4) . . . . ?
C14B C14A C10A N10 -0.1(6) . . . . ?
C14 C14A C10A C11 1.0(8) . . . . ?
C14B C14A C10A C11 176.8(5) . . . . ?
C9 N8 C7 C6 109.2(6) . . . . ?
N8 C7 C6 C5 -79.9(6) . . . . ?
C7 C6 C5 C4A 81.1(6) . . . . ?
C6 C5 C4A C4 85.7(6) . . . . ?
C6 C5 C4A C14C -98.0(6) . . . . ?
C14C C4A C4 C3 -1.4(8) . . . . ?
C5 C4A C4 C3 175.1(5) . . . . ?
C4A C4 C3 C2 -0.5(8) . . . . ?
C4 C3 C2 C1 1.6(8) . . . . ?
C3 C2 C1 C14C -0.7(8) . . . . ?
C2 C1 C14C C4A -1.2(8) . . . . ?
C2 C1 C14C C14B 177.4(5) . . . . ?
C4 C4A C14C C1 2.3(7) . . . . ?
C5 C4A C14C C1 -174.1(5) . . . . ?
C4 C4A C14C C14B -176.3(5) . . . . ?
C5 C4A C14C C14B 7.3(8) . . . . ?
C9A C14B C14C C1 -102.1(6) . . . . ?
C14A C14B C14C C1 66.1(7) . . . . ?
C9A C14B C14C C4A 76.5(7) . . . . ?
C14A C14B C14C C4A -115.3(6) . . . . ?
C10A C14A C14 C13 0.8(7) . . . . ?
C14B C14A C14 C13 -173.7(5) . . . . ?
C14A C14 C13 C12 -1.7(7) . . . . ?
C14A C14 C13 Br1 176.4(3) . . . . ?
C14 C13 C12 C11 0.9(7) . . . . ?
Br1 C13 C12 C11 -177.3(4) . . . . ?
C13 C12 C11 C10A 0.8(7) . . . . ?
N10 C10A C11 C12 174.3(5) . . . . ?
C14A C10A C11 C12 -1.8(7) . . . . ?
C50 N49 C48 C53 0.1(8) . . . . ?
C50 N49 C48 C47 -179.5(5) . . . . ?
C48 N49 C50 C51 0.6(9) . . . . ?
N49 C50 C51 C52 -0.6(9) . . . . ?
C50 C51 C52 C53 -0.1(8) . . . . ?
C51 C52 C53 C48 0.8(8) . . . . ?
N49 C48 C53 C52 -0.8(8) . . . . ?
C47 C48 C53 C52 178.8(5) . . . . ?
N45 N46 C47 C54 0.5(7) . . . . ?
N45 N46 C47 C48 -178.1(4) . . . . ?
N49 C48 C47 N46 179.4(5) . . . . ?
C53 C48 C47 N46 -0.2(7) . . . . ?
N49 C48 C47 C54 0.7(7) . . . . ?
C53 C48 C47 C54 -178.9(5) . . . . ?
N46 N45 C39 N38 -1.0(7) . . . . ?
N46 N45 C39 C39A -175.1(4) . . . . ?
C37 N38 C39 N45 163.6(5) . . . . ?
C37 N38 C39 C39A -22.4(7) . . . . ?
C40A N40 C39A C44B -2.9(6) . . . . ?
C40A N40 C39A C39 168.2(5) . . . . ?
N45 C39 C39A N40 -67.9(7) . . . . ?
N38 C39 C39A N40 117.5(5) . . . . ?
N45 C39 C39A C44B 101.8(6) . . . . ?
N38 C39 C39A C44B -72.8(7) . . . . ?
N40 C39A C44B C44A 3.0(6) . . . . ?
C39 C39A C44B C44A -167.8(5) . . . . ?
N40 C39A C44B C44C 176.7(5) . . . . ?
C39 C39A C44B C44C 5.9(9) . . . . ?
C39A C44B C44A C40A -2.1(6) . . . . ?
C44C C44B C44A C40A -175.8(5) . . . . ?
C39A C44B C44A C44 173.4(5) . . . . ?
C44C C44B C44A C44 -0.4(9) . . . . ?
C39A N40 C40A C41 -174.7(5) . . . . ?
C39A N40 C40A C44A 1.4(5) . . . . ?
C44 C44A C40A N40 -175.6(4) . . . . ?
C44B C44A C40A N40 0.4(6) . . . . ?
C44 C44A C40A C41 0.9(8) . . . . ?
C44B C44A C40A C41 176.9(4) . . . . ?
C39 N38 C37 C36 109.4(6) . . . . ?
N38 C37 C36 C35 -80.3(6) . . . . ?
C37 C36 C35 C34A 83.4(6) . . . . ?
C36 C35 C34A C34 89.1(6) . . . . ?
C36 C35 C34A C44C -94.9(6) . . . . ?
C44C C34A C34 C33 -0.8(8) . . . . ?
C35 C34A C34 C33 175.4(5) . . . . ?
C34A C34 C33 C32 1.0(8) . . . . ?
C34 C33 C32 C31 -1.5(8) . . . . ?
C33 C32 C31 C44C 2.0(8) . . . . ?
C32 C31 C44C C34A -1.9(8) . . . . ?
C32 C31 C44C C44B -178.5(5) . . . . ?
C34 C34A C44C C31 1.2(7) . . . . ?
C35 C34A C44C C31 -174.8(5) . . . . ?
C34 C34A C44C C44B 177.8(5) . . . . ?
C35 C34A C44C C44B 1.7(8) . . . . ?
C39A C44B C44C C31 -105.8(6) . . . . ?
C44A C44B C44C C31 66.6(7) . . . . ?
C39A C44B C44C C34A 77.7(7) . . . . ?
C44A C44B C44C C34A -110.0(6) . . . . ?
C40A C44A C44 C43 0.6(7) . . . . ?
C44B C44A C44 C43 -174.4(5) . . . . ?
C44A C44 C43 C42 -1.2(7) . . . . ?
C44A C44 C43 Br2 176.4(4) . . . . ?
C44 C43 C42 C41 0.4(8) . . . . ?
Br2 C43 C42 C41 -177.2(4) . . . . ?
C43 C42 C41 C40A 1.0(7) . . . . ?
N40 C40A C41 C42 174.0(5) . . . . ?
C44A C40A C41 C42 -1.6(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N10 H10 N45 0.88 2.29 3.102(6) 153.1 .
N40 H40 N15 0.88 2.33 3.143(6) 153.9 .
C23 H23 Br1 0.95 3.05 3.650(5) 123.0 1_655
C7 H7B Cl4 0.99 2.86 3.436(6) 118.2 2_766
C14 H14 Cl3 0.95 2.84 3.736(5) 156.7 2_666
C44 H44 Cl2 0.95 2.91 3.795(6) 156.1 1_545
C62 H62A N19 0.99 2.40 3.364(7) 164.0 .
C62 H62B Cl3 0.99 2.81 3.438(6) 121.9 2_756
C61 H61B N49 0.99 2.52 3.415(9) 150.0 2_675

_refine_diff_density_max         1.553
_refine_diff_density_min         -1.534
_refine_diff_density_rms         0.146

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_cw1059n
_database_code_depnum_ccdc_archive 'CCDC 2261966'
loop_
_audit_author_name
_audit_author_address
'Vladimir Arion'
;University of Vienna
Austria
;
_audit_update_record             
;
2023-05-10 deposited with the CCDC.	2023-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 Cl Cu N5, C3 H8 O, C H4 O'
_chemical_formula_sum            'C29 H34 Cl Cu N5 O2'
_chemical_formula_weight         583.60

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'
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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6320(8)
_cell_length_b                   11.6124(12)
_cell_length_c                   16.5842(17)
_cell_angle_alpha                90.668(3)
_cell_angle_beta                 93.199(3)
_cell_angle_gamma                105.631(3)
_cell_volume                     1412.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4348
_cell_measurement_theta_min      2.13
_cell_measurement_theta_max      25.56

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             610
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.903
_shelx_estimated_absorpt_T_min   0.466
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4655
_exptl_absorpt_correction_T_max  0.9563
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40742
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.822
_diffrn_reflns_theta_max         28.353
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7005
_reflns_number_gt                5958
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0367P)²+1.3651P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7005
_refine_ls_number_parameters     349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0966
_refine_ls_wR_factor_gt          0.0913
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Cu Cu 0.13064(3) 0.39217(2) 0.47169(2) 0.02189(7) Uani 1 1 d . . . . .
Cl Cl 0.01917(8) 0.28347(5) 0.57424(3) 0.03672(13) Uani 1 1 d . . . . .
C1 C 0.3025(3) 0.13909(18) 0.18945(12) 0.0267(4) Uani 1 1 d . . . . .
H1 H 0.3301 0.1969 0.1487 0.032 Uiso 1 1 calc R U . . .
C2 C 0.4298(3) 0.07913(19) 0.21363(14) 0.0308(4) Uani 1 1 d . . . . .
H2 H 0.5434 0.0953 0.1893 0.037 Uiso 1 1 calc R U . . .
C3 C 0.3907(3) -0.00468(19) 0.27352(15) 0.0331(5) Uani 1 1 d . . . . .
H3 H 0.4784 -0.0450 0.2912 0.040 Uiso 1 1 calc R U . . .
C4 C 0.2230(3) -0.02957(18) 0.30763(14) 0.0309(5) Uani 1 1 d . . . . .
H4 H 0.1968 -0.0875 0.3484 0.037 Uiso 1 1 calc R U . . .
C4A C 0.0919(3) 0.02896(17) 0.28326(13) 0.0241(4) Uani 1 1 d . . . . .
C5 C -0.0911(3) -0.00584(18) 0.31995(14) 0.0279(4) Uani 1 1 d . . . . .
H5A H -0.1201 -0.0919 0.3323 0.033 Uiso 1 1 calc R U . . .
H5B H -0.1847 0.0044 0.2789 0.033 Uiso 1 1 calc R U . . .
C6 C -0.1065(3) 0.06440(19) 0.39719(14) 0.0299(4) Uani 1 1 d . . . . .
H6A H -0.2027 0.0134 0.4288 0.036 Uiso 1 1 calc R U . . .
H6B H 0.0100 0.0791 0.4301 0.036 Uiso 1 1 calc R U . . .
C7 C -0.1498(3) 0.18418(17) 0.38500(13) 0.0253(4) Uani 1 1 d . . . . .
H7A H -0.2282 0.1779 0.3346 0.030 Uiso 1 1 calc R U . . .
H7B H -0.2216 0.1983 0.4302 0.030 Uiso 1 1 calc R U . . .
N8 N 0.0081(2) 0.28919(14) 0.38014(10) 0.0226(3) Uani 1 1 d . . . . .
C9 C 0.0540(3) 0.34062(17) 0.31107(12) 0.0217(4) Uani 1 1 d . . . . .
C9A C -0.0242(3) 0.28345(17) 0.23208(12) 0.0227(4) Uani 1 1 d . . . . .
N10 N -0.1387(2) 0.33061(15) 0.18340(10) 0.0246(3) Uani 1 1 d . . . . .
H10 H -0.1736 0.3950 0.1946 0.030 Uiso 1 1 calc R U . . .
C10A C -0.1890(3) 0.25972(18) 0.11444(12) 0.0247(4) Uani 1 1 d . . . . .
C11 C -0.3069(3) 0.2676(2) 0.04869(14) 0.0352(5) Uani 1 1 d . . . . .
H11 H -0.3652 0.3303 0.0456 0.042 Uiso 1 1 calc R U . . .
C12 C -0.3354(4) 0.1808(3) -0.01149(15) 0.0457(6) Uani 1 1 d . . . . .
H12 H -0.4146 0.1841 -0.0572 0.055 Uiso 1 1 calc R U . . .
C13 C -0.2509(4) 0.0875(3) -0.00727(15) 0.0448(6) Uani 1 1 d . . . . .
H13 H -0.2746 0.0286 -0.0497 0.054 Uiso 1 1 calc R U . . .
C14 C -0.1338(3) 0.0800(2) 0.05757(13) 0.0330(5) Uani 1 1 d . . . . .
H14 H -0.0761 0.0170 0.0600 0.040 Uiso 1 1 calc R U . . .
C14A C -0.1017(3) 0.16702(17) 0.11979(12) 0.0232(4) Uani 1 1 d . . . . .
C14B C 0.0036(3) 0.18386(17) 0.19554(11) 0.0223(4) Uani 1 1 d . . . . .
C14C C 0.1336(3) 0.11595(16) 0.22410(12) 0.0220(4) Uani 1 1 d . . . . .
N15 N 0.1788(2) 0.44815(14) 0.30648(10) 0.0239(3) Uani 1 1 d . . . . .
N16 N 0.2350(2) 0.49125(14) 0.38321(10) 0.0220(3) Uani 1 1 d . . . . .
C17 C 0.3543(3) 0.59279(17) 0.39992(12) 0.0239(4) Uani 1 1 d . . . . .
C18 C 0.3935(3) 0.61735(17) 0.48747(12) 0.0237(4) Uani 1 1 d . . . . .
N19 N 0.2920(2) 0.53477(15) 0.53572(10) 0.0245(3) Uani 1 1 d . . . . .
C20 C 0.3173(3) 0.54871(19) 0.61616(13) 0.0284(4) Uani 1 1 d . . . . .
H20 H 0.2446 0.4908 0.6492 0.034 Uiso 1 1 calc R U . . .
C21 C 0.4477(3) 0.6459(2) 0.65265(13) 0.0309(5) Uani 1 1 d . . . . .
H21 H 0.4638 0.6544 0.7098 0.037 Uiso 1 1 calc R U . . .
C22 C 0.5526(3) 0.7295(2) 0.60429(14) 0.0313(5) Uani 1 1 d . . . . .
H22 H 0.6428 0.7962 0.6279 0.038 Uiso 1 1 calc R U . . .
C23 C 0.5259(3) 0.71575(18) 0.52084(13) 0.0282(4) Uani 1 1 d . . . . .
H23 H 0.5973 0.7730 0.4869 0.034 Uiso 1 1 calc R U . . .
C24 C 0.4436(3) 0.6779(2) 0.33893(14) 0.0366(5) Uani 1 1 d . . . . .
H24A H 0.5763 0.6944 0.3474 0.055 Uiso 1 1 calc R U . . .
H24B H 0.4085 0.7527 0.3445 0.055 Uiso 1 1 calc R U . . .
H24C H 0.4051 0.6429 0.2846 0.055 Uiso 1 1 calc R U . . .
O1 O 0.3784(3) 0.4786(2) 0.16688(12) 0.0636(6) Uani 1 1 d . . . . .
H1A H 0.3060 0.4693 0.2041 0.095 Uiso 1 1 calc R U . . .
C25 C 0.2800(4) 0.4560(3) 0.09261(17) 0.0525(7) Uani 1 1 d . . . . .
H25A H 0.3645 0.4701 0.0491 0.079 Uiso 1 1 calc R U . . .
H25B H 0.2004 0.5094 0.0870 0.079 Uiso 1 1 calc R U . . .
H25C H 0.2058 0.3727 0.0894 0.079 Uiso 1 1 calc R U . . .
O2 O 0.2556(2) 0.45817(15) 0.81010(13) 0.0474(5) Uani 1 1 d . . . . .
H2A H 0.3674 0.4683 0.8217 0.071 Uiso 1 1 calc R U . . .
C26 C 0.2561(6) 0.2679(4) 0.8668(3) 0.1062(17) Uani 1 1 d . . . . .
H26A H 0.1917 0.1829 0.8593 0.159 Uiso 1 1 calc R U . . .
H26B H 0.2577 0.2918 0.9238 0.159 Uiso 1 1 calc R U . . .
H26C H 0.3815 0.2815 0.8507 0.159 Uiso 1 1 calc R U . . .
C27 C 0.1638(5) 0.3380(3) 0.8177(3) 0.0856(14) Uani 1 1 d . . . . .
H27 H 0.1753 0.3060 0.7626 0.103 Uiso 1 1 calc R U . . .
C28 C -0.0288(5) 0.3169(3) 0.8179(3) 0.0799(11) Uani 1 1 d . . . . .
H28A H -0.0872 0.2310 0.8108 0.120 Uiso 1 1 calc R U . . .
H28B H -0.0713 0.3597 0.7737 0.120 Uiso 1 1 calc R U . . .
H28C H -0.0604 0.3455 0.8696 0.120 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
Cu N16 1.9460(16) . ?
Cu N8 1.9511(16) . ?
Cu N19 2.0249(17) . ?
Cu Cl 2.2006(6) . ?
C1 C2 1.385(3) . ?
C1 C14C 1.401(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.386(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C4A 1.398(3) . ?
C4 H4 0.9500 . ?
C4A C14C 1.403(3) . ?
C4A C5 1.510(3) . ?
C5 C6 1.538(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.527(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N8 1.472(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
N8 C9 1.319(3) . ?
C9 N15 1.357(2) . ?
C9 C9A 1.481(3) . ?
C9A C14B 1.371(3) . ?
C9A N10 1.380(2) . ?
N10 C10A 1.375(3) . ?
N10 H10 0.8800 . ?
C10A C11 1.395(3) . ?
C10A C14A 1.411(3) . ?
C11 C12 1.376(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.404(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9500 . ?
C14 C14A 1.400(3) . ?
C14 H14 0.9500 . ?
C14A C14B 1.435(3) . ?
C14B C14C 1.486(3) . ?
N15 N16 1.365(2) . ?
N16 C17 1.297(2) . ?
C17 C18 1.475(3) . ?
C17 C24 1.484(3) . ?
C18 N19 1.359(3) . ?
C18 C23 1.391(3) . ?
N19 C20 1.339(3) . ?
C20 C21 1.393(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.389(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O1 C25 1.390(3) . ?
O1 H1A 0.8400 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
O2 C27 1.393(4) . ?
O2 H2A 0.8400 . ?
C26 C27 1.443(5) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.424(5) . ?
C27 H27 1.0000 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

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
N16 Cu N8 80.23(7) . . ?
N16 Cu N19 80.39(7) . . ?
N8 Cu N19 160.60(7) . . ?
N16 Cu Cl 178.28(5) . . ?
N8 Cu Cl 101.43(5) . . ?
N19 Cu Cl 97.96(5) . . ?
C2 C1 C14C 121.11(19) . . ?
C2 C1 H1 119.4 . . ?
C14C C1 H1 119.4 . . ?
C1 C2 C3 119.7(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C4A 121.3(2) . . ?
C3 C4 H4 119.3 . . ?
C4A C4 H4 119.3 . . ?
C4 C4A C14C 118.75(18) . . ?
C4 C4A C5 118.88(18) . . ?
C14C C4A C5 122.36(18) . . ?
C4A C5 C6 115.85(17) . . ?
C4A C5 H5A 108.3 . . ?
C6 C5 H5A 108.3 . . ?
C4A C5 H5B 108.3 . . ?
C6 C5 H5B 108.3 . . ?
H5A C5 H5B 107.4 . . ?
C7 C6 C5 116.14(18) . . ?
C7 C6 H6A 108.3 . . ?
C5 C6 H6A 108.3 . . ?
C7 C6 H6B 108.3 . . ?
C5 C6 H6B 108.3 . . ?
H6A C6 H6B 107.4 . . ?
N8 C7 C6 116.06(16) . . ?
N8 C7 H7A 108.3 . . ?
C6 C7 H7A 108.3 . . ?
N8 C7 H7B 108.3 . . ?
C6 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C9 N8 C7 122.02(16) . . ?
C9 N8 Cu 111.07(13) . . ?
C7 N8 Cu 125.04(13) . . ?
N8 C9 N15 123.02(17) . . ?
N8 C9 C9A 122.23(17) . . ?
N15 C9 C9A 114.73(17) . . ?
C14B C9A N10 110.42(17) . . ?
C14B C9A C9 128.37(17) . . ?
N10 C9A C9 121.20(17) . . ?
C10A N10 C9A 108.33(16) . . ?
C10A N10 H10 125.8 . . ?
C9A N10 H10 125.8 . . ?
N10 C10A C11 130.1(2) . . ?
N10 C10A C14A 107.89(17) . . ?
C11 C10A C14A 121.95(19) . . ?
C12 C11 C10A 117.2(2) . . ?
C12 C11 H11 121.4 . . ?
C10A C11 H11 121.4 . . ?
C11 C12 C13 121.9(2) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C14 C13 C12 120.9(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C14A 118.7(2) . . ?
C13 C14 H14 120.7 . . ?
C14A C14 H14 120.7 . . ?
C14 C14A C10A 119.44(19) . . ?
C14 C14A C14B 133.31(19) . . ?
C10A C14A C14B 107.21(17) . . ?
C9A C14B C14A 106.14(17) . . ?
C9A C14B C14C 126.72(17) . . ?
C14A C14B C14C 126.78(17) . . ?
C1 C14C C4A 119.31(18) . . ?
C1 C14C C14B 118.31(18) . . ?
C4A C14C C14B 122.37(17) . . ?
C9 N15 N16 108.25(15) . . ?
C17 N16 N15 123.78(17) . . ?
C17 N16 Cu 118.87(14) . . ?
N15 N16 Cu 117.35(12) . . ?
N16 C17 C18 113.00(17) . . ?
N16 C17 C24 124.81(19) . . ?
C18 C17 C24 122.19(18) . . ?
N19 C18 C23 120.60(19) . . ?
N19 C18 C17 115.28(17) . . ?
C23 C18 C17 124.11(19) . . ?
C20 N19 C18 119.95(18) . . ?
C20 N19 Cu 127.55(15) . . ?
C18 N19 Cu 112.23(13) . . ?
N19 C20 C21 121.7(2) . . ?
N19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C22 C21 C20 118.8(2) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C21 C22 C23 119.7(2) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C22 C23 C18 119.3(2) . . ?
C22 C23 H23 120.4 . . ?
C18 C23 H23 120.4 . . ?
C17 C24 H24A 109.5 . . ?
C17 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C17 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C25 O1 H1A 109.5 . . ?
O1 C25 H25A 109.5 . . ?
O1 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O1 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 O2 H2A 109.5 . . ?
C27 C26 H26A 109.5 . . ?
C27 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C27 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O2 C27 C28 113.3(3) . . ?
O2 C27 C26 116.5(3) . . ?
C28 C27 C26 120.4(4) . . ?
O2 C27 H27 100.5 . . ?
C28 C27 H27 100.5 . . ?
C26 C27 H27 100.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
C14C C1 C2 C3 -0.5(3) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
C2 C3 C4 C4A -0.5(3) . . . . ?
C3 C4 C4A C14C -1.2(3) . . . . ?
C3 C4 C4A C5 177.3(2) . . . . ?
C4 C4A C5 C6 90.2(2) . . . . ?
C14C C4A C5 C6 -91.4(2) . . . . ?
C4A C5 C6 C7 84.0(2) . . . . ?
C5 C6 C7 N8 -89.4(2) . . . . ?
C6 C7 N8 C9 105.2(2) . . . . ?
C6 C7 N8 Cu -91.8(2) . . . . ?
C7 N8 C9 N15 168.69(17) . . . . ?
Cu N8 C9 N15 3.5(2) . . . . ?
C7 N8 C9 C9A -12.8(3) . . . . ?
Cu N8 C9 C9A -177.96(14) . . . . ?
N8 C9 C9A C14B -68.9(3) . . . . ?
N15 C9 C9A C14B 109.7(2) . . . . ?
N8 C9 C9A N10 112.5(2) . . . . ?
N15 C9 C9A N10 -68.9(2) . . . . ?
C14B C9A N10 C10A 0.9(2) . . . . ?
C9 C9A N10 C10A 179.76(17) . . . . ?
C9A N10 C10A C11 177.6(2) . . . . ?
C9A N10 C10A C14A -0.8(2) . . . . ?
N10 C10A C11 C12 -178.2(2) . . . . ?
C14A C10A C11 C12 0.0(3) . . . . ?
C10A C11 C12 C13 0.3(4) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C13 C14 C14A 0.5(4) . . . . ?
C13 C14 C14A C10A -0.2(3) . . . . ?
C13 C14 C14A C14B 177.3(2) . . . . ?
N10 C10A C14A C14 178.47(18) . . . . ?
C11 C10A C14A C14 0.0(3) . . . . ?
N10 C10A C14A C14B 0.4(2) . . . . ?
C11 C10A C14A C14B -178.15(19) . . . . ?
N10 C9A C14B C14A -0.7(2) . . . . ?
C9 C9A C14B C14A -179.40(19) . . . . ?
N10 C9A C14B C14C 172.70(18) . . . . ?
C9 C9A C14B C14C -6.0(3) . . . . ?
C14 C14A C14B C9A -177.5(2) . . . . ?
C10A C14A C14B C9A 0.2(2) . . . . ?
C14 C14A C14B C14C 9.1(4) . . . . ?
C10A C14A C14B C14C -173.19(18) . . . . ?
C2 C1 C14C C4A -1.2(3) . . . . ?
C2 C1 C14C C14B 179.77(18) . . . . ?
C4 C4A C14C C1 1.9(3) . . . . ?
C5 C4A C14C C1 -176.48(18) . . . . ?
C4 C4A C14C C14B -179.04(18) . . . . ?
C5 C4A C14C C14B 2.5(3) . . . . ?
C9A C14B C14C C1 -98.3(2) . . . . ?
C14A C14B C14C C1 73.7(3) . . . . ?
C9A C14B C14C C4A 82.6(3) . . . . ?
C14A C14B C14C C4A -105.3(2) . . . . ?
N8 C9 N15 N16 -3.0(3) . . . . ?
C9A C9 N15 N16 178.43(15) . . . . ?
C9 N15 N16 C17 -179.94(18) . . . . ?
C9 N15 N16 Cu 0.88(19) . . . . ?
N15 N16 C17 C18 -178.93(16) . . . . ?
Cu N16 C17 C18 0.2(2) . . . . ?
N15 N16 C17 C24 1.5(3) . . . . ?
Cu N16 C17 C24 -179.36(17) . . . . ?
N16 C17 C18 N19 -3.9(3) . . . . ?
C24 C17 C18 N19 175.71(19) . . . . ?
N16 C17 C18 C23 175.03(18) . . . . ?
C24 C17 C18 C23 -5.4(3) . . . . ?
C23 C18 N19 C20 0.9(3) . . . . ?
C17 C18 N19 C20 179.89(17) . . . . ?
C23 C18 N19 Cu -173.52(15) . . . . ?
C17 C18 N19 Cu 5.5(2) . . . . ?
C18 N19 C20 C21 -0.7(3) . . . . ?
Cu N19 C20 C21 172.83(15) . . . . ?
N19 C20 C21 C22 0.0(3) . . . . ?
C20 C21 C22 C23 0.4(3) . . . . ?
C21 C22 C23 C18 -0.2(3) . . . . ?
N19 C18 C23 C22 -0.5(3) . . . . ?
C17 C18 C23 C22 -179.38(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7B Cl 0.99 2.92 3.392(2) 110.1 .
N10 H10 O2 0.88 1.97 2.830(2) 165.6 2_566
C20 H20 Cl 0.95 2.79 3.338(2) 117.9 .
O1 H1A N15 0.84 1.99 2.816(3) 168.5 .
O2 H2A O1 0.84 1.87 2.693(3) 167.0 2_666

_refine_diff_density_max         1.161
_refine_diff_density_min         -0.923
_refine_diff_density_rms         0.062

_shelxl_version_number           2014-3

