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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_be22roc1n
_database_code_depnum_ccdc_archive 'CCDC 2174268'
loop_
_audit_author_name
_audit_author_address
'Guillermo Zaragoza'
;Unidade de Difraccion de Raios X Edificio CACTUS Universidade de Santiago de Compostela
Spain
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-07-28 downloaded from the CCDC.
;

_audit_creation_date             2013-03-25T13:37:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        CuL'
_chemical_formula_moiety         '2(C9 H13 Cl2 Cu N5), H2 O'
_chemical_formula_sum            'C18 H28 Cl4 Cu2 N10 O'
_chemical_formula_weight         669.38
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   16.3718(13)
_cell_length_b                   8.9832(7)
_cell_length_c                   17.4044(14)
_cell_angle_alpha                90
_cell_angle_beta                 93.781(4)
_cell_angle_gamma                90
_cell_volume                     2554.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1889
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      23.16
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       Plate
_exptl_crystal_colour            Green
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_absorpt_correction_T_min  0.8274
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'BRUKER APPEX-II CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_number            334364
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             4637
_reflns_number_gt                3418
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'APPEX2 (BRUKER AXS, 2005)'
_computing_cell_refinement       'APPEX2 (BRUKER AXS, 2005)'
_computing_data_reduction        'APPEX2 (BRUKER AXS, 2005)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0423P)²+5.2443P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4637
_refine_ls_number_parameters     350
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1028
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.189
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.114

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.41053(3) 0.43285(6) 0.20686(3) 0.01300(15) Uani 1 1 d . . .
Cl3 Cl 0.33207(7) 0.64542(12) 0.14679(6) 0.0169(3) Uani 1 1 d . . .
Cl2 Cl 0.37422(7) 0.44293(12) 0.32857(6) 0.0172(3) Uani 1 1 d . . .
N1 N 0.4636(2) 0.3599(4) 0.1181(2) 0.0131(8) Uani 1 1 d . . .
C2 C 0.5355(3) 0.4218(5) 0.1017(3) 0.0160(10) Uani 1 1 d . . .
C3 C 0.5730(3) 0.3746(5) 0.0366(3) 0.0194(11) Uani 1 1 d . . .
H3 H 0.6234 0.417 0.0236 0.023 Uiso 1 1 calc R . .
C4 C 0.5354(3) 0.2646(5) -0.0089(3) 0.0192(11) Uani 1 1 d . . .
H4 H 0.5599 0.2327 -0.0541 0.023 Uiso 1 1 calc R . .
C5 C 0.4628(3) 0.2004(5) 0.0105(3) 0.0182(10) Uani 1 1 d . . .
H5 H 0.4377 0.1234 -0.0202 0.022 Uiso 1 1 calc R . .
C6 C 0.4276(3) 0.2513(5) 0.0756(2) 0.0134(10) Uani 1 1 d . . .
C21 C 0.5657(3) 0.5319(5) 0.1589(3) 0.0161(10) Uani 1 1 d . . .
N22 N 0.5191(2) 0.5455(4) 0.2163(2) 0.0170(9) Uani 1 1 d . . .
N23 N 0.5407(3) 0.6325(5) 0.2783(3) 0.0238(10) Uani 1 1 d . . .
H23A H 0.572(3) 0.700(6) 0.271(3) 0.029 Uiso 1 1 d . . .
H23B H 0.499(3) 0.659(6) 0.298(3) 0.029 Uiso 1 1 d . . .
C61 C 0.3531(3) 0.1948(5) 0.1088(2) 0.0158(10) Uani 1 1 d . . .
N62 N 0.3357(2) 0.2612(4) 0.1718(2) 0.0152(8) Uani 1 1 d . . .
N63 N 0.2666(2) 0.2258(5) 0.2074(2) 0.0184(9) Uani 1 1 d . . .
H63A H 0.276(3) 0.241(5) 0.257(3) 0.022 Uiso 1 1 d . . .
H63B H 0.255(3) 0.131(6) 0.206(3) 0.022 Uiso 1 1 d . . .
C211 C 0.6430(3) 0.6166(5) 0.1521(3) 0.0231(11) Uani 1 1 d . . .
H21A H 0.6316 0.7236 0.1546 0.035 Uiso 1 1 calc R . .
H21B H 0.6657 0.5932 0.1029 0.035 Uiso 1 1 calc R . .
H21C H 0.6825 0.589 0.1945 0.035 Uiso 1 1 calc R . .
C611 C 0.3044(3) 0.0713(5) 0.0730(3) 0.0238(11) Uani 1 1 d . . .
H61A H 0.31 -0.017 0.106 0.036 Uiso 1 1 calc R . .
H61B H 0.3244 0.0485 0.0224 0.036 Uiso 1 1 calc R . .
H61C H 0.2467 0.1006 0.0668 0.036 Uiso 1 1 calc R . .
Cu1B Cu 0.54857(3) 0.07562(6) 0.28662(3) 0.01500(15) Uani 1 1 d . . .
Cl2B Cl 0.53618(7) -0.01587(13) 0.16769(6) 0.0215(3) Uani 1 1 d . . .
Cl3B Cl 0.65690(6) -0.09893(12) 0.34656(6) 0.0162(2) Uani 1 1 d . . .
N1B N 0.5394(2) 0.1899(4) 0.3789(2) 0.0135(8) Uani 1 1 d . . .
C2B C 0.5943(3) 0.2986(5) 0.3942(2) 0.0144(10) Uani 1 1 d . . .
C3B C 0.5933(3) 0.3780(5) 0.4622(3) 0.0205(11) Uani 1 1 d . . .
H3B H 0.6311 0.4564 0.4737 0.025 Uiso 1 1 calc R . .
C4B C 0.5348(3) 0.3386(5) 0.5131(3) 0.0219(11) Uani 1 1 d . . .
H4B H 0.5341 0.3895 0.5609 0.026 Uiso 1 1 calc R . .
C5B C 0.4777(3) 0.2282(5) 0.4965(3) 0.0177(10) Uani 1 1 d . . .
H5B H 0.4377 0.2032 0.5314 0.021 Uiso 1 1 calc R . .
C6B C 0.4813(3) 0.1549(5) 0.4263(2) 0.0147(10) Uani 1 1 d . . .
C21B C 0.6504(3) 0.3217(5) 0.3318(3) 0.0161(10) Uani 1 1 d . . .
N22B N 0.6342(2) 0.2372(4) 0.2724(2) 0.0185(9) Uani 1 1 d . . .
N23B N 0.6763(3) 0.2441(5) 0.2082(2) 0.0271(10) Uani 1 1 d D . .
H23C H 0.719(3) 0.299(6) 0.211(3) 0.032 Uiso 1 1 d . . .
H23D H 0.663(3) 0.170(4) 0.177(2) 0.032 Uiso 1 1 d D . .
C61B C 0.4266(3) 0.0372(5) 0.3951(3) 0.0152(10) Uani 1 1 d . . .
N62B N 0.4448(2) -0.0122(4) 0.3280(2) 0.0151(8) Uani 1 1 d . . .
N63B N 0.4024(3) -0.1263(5) 0.2926(3) 0.0221(10) Uani 1 1 d . . .
H63C H 0.417(3) -0.129(5) 0.240(3) 0.026 Uiso 1 1 d . . .
H63D H 0.355(3) -0.131(6) 0.300(3) 0.026 Uiso 1 1 d . . .
C22B C 0.7166(3) 0.4348(5) 0.3399(3) 0.0237(11) Uani 1 1 d . . .
H22A H 0.7505 0.4285 0.2957 0.035 Uiso 1 1 calc R . .
H22B H 0.7505 0.4162 0.3874 0.035 Uiso 1 1 calc R . .
H22C H 0.6923 0.5344 0.342 0.035 Uiso 1 1 calc R . .
C62B C 0.3548(3) -0.0182(5) 0.4349(3) 0.0199(11) Uani 1 1 d . . .
H62A H 0.3046 0.026 0.411 0.03 Uiso 1 1 calc R . .
H62B H 0.3607 0.0098 0.4894 0.03 Uiso 1 1 calc R . .
H62C H 0.3518 -0.1268 0.4304 0.03 Uiso 1 1 calc R . .
O1 O 0.7415(3) 0.6938(5) 0.4797(2) 0.0506(12) Uani 1 1 d D . .
H1O H 0.757(3) 0.731(7) 0.5221(18) 0.061 Uiso 1 1 d D . .
H2O H 0.721(4) 0.762(5) 0.452(3) 0.061 Uiso 1 1 d D . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.935(3) . ?
Cu1 N62 2.038(4) . ?
Cu1 N22 2.043(4) . ?
Cu1 Cl2 2.2394(12) . ?
Cu1 Cl3 2.4925(12) . ?
N1 C6 1.339(5) . ?
N1 C2 1.349(5) . ?
C2 C3 1.390(6) . ?
C2 C21 1.465(6) . ?
C3 C4 1.386(6) . ?
C3 H3 0.95 . ?
C4 C5 1.384(6) . ?
C4 H4 0.95 . ?
C5 C6 1.382(6) . ?
C5 H5 0.95 . ?
C6 C61 1.474(6) . ?
C21 N22 1.303(6) . ?
C21 C211 1.488(6) . ?
N22 N23 1.360(5) . ?
N23 H23A 0.81(5) . ?
N23 H23B 0.83(5) . ?
C61 N62 1.297(5) . ?
C61 C611 1.479(6) . ?
N62 N63 1.363(5) . ?
N63 H63A 0.87(5) . ?
N63 H63B 0.87(5) . ?
C211 H21A 0.98 . ?
C211 H21B 0.98 . ?
C211 H21C 0.98 . ?
C611 H61A 0.98 . ?
C611 H61B 0.98 . ?
C611 H61C 0.98 . ?
Cu1B N1B 1.920(4) . ?
Cu1B N22B 2.044(4) . ?
Cu1B N62B 2.047(4) . ?
Cu1B Cl2B 2.2238(12) . ?
Cu1B Cl3B 2.5394(12) . ?
N1B C6B 1.339(5) . ?
N1B C2B 1.341(5) . ?
C2B C3B 1.382(6) . ?
C2B C21B 1.483(6) . ?
C3B C4B 1.394(7) . ?
C3B H3B 0.95 . ?
C4B C5B 1.380(6) . ?
C4B H4B 0.95 . ?
C5B C6B 1.391(6) . ?
C5B H5B 0.95 . ?
C6B C61B 1.466(6) . ?
C21B N22B 1.296(6) . ?
C21B C22B 1.486(6) . ?
N22B N23B 1.353(5) . ?
N23B H23C 0.86(5) . ?
N23B H23D 0.878(10) . ?
C61B N62B 1.302(5) . ?
C61B C62B 1.489(6) . ?
N62B N63B 1.362(5) . ?
N63B H63C 0.95(5) . ?
N63B H63D 0.80(5) . ?
C22B H22A 0.98 . ?
C22B H22B 0.98 . ?
C22B H22C 0.98 . ?
C62B H62A 0.98 . ?
C62B H62B 0.98 . ?
C62B H62C 0.98 . ?
O1 H1O 0.836(9) . ?
O1 H2O 0.833(10) . ?

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
N1 Cu1 N62 78.35(14) . . ?
N1 Cu1 N22 78.31(15) . . ?
N62 Cu1 N22 154.41(14) . . ?
N1 Cu1 Cl2 158.36(11) . . ?
N62 Cu1 Cl2 97.00(10) . . ?
N22 Cu1 Cl2 100.83(11) . . ?
N1 Cu1 Cl3 99.84(11) . . ?
N62 Cu1 Cl3 99.85(10) . . ?
N22 Cu1 Cl3 94.34(11) . . ?
Cl2 Cu1 Cl3 101.78(4) . . ?
C6 N1 C2 122.8(4) . . ?
C6 N1 Cu1 118.9(3) . . ?
C2 N1 Cu1 118.3(3) . . ?
N1 C2 C3 119.0(4) . . ?
N1 C2 C21 113.3(4) . . ?
C3 C2 C21 127.7(4) . . ?
C4 C3 C2 118.7(4) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C5 C4 C3 120.9(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 118.3(4) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
N1 C6 C5 120.2(4) . . ?
N1 C6 C61 112.3(4) . . ?
C5 C6 C61 127.4(4) . . ?
N22 C21 C2 113.3(4) . . ?
N22 C21 C211 123.8(4) . . ?
C2 C21 C211 122.9(4) . . ?
C21 N22 N23 121.8(4) . . ?
C21 N22 Cu1 116.3(3) . . ?
N23 N22 Cu1 121.9(3) . . ?
N22 N23 H23A 116(4) . . ?
N22 N23 H23B 108(4) . . ?
H23A N23 H23B 115(5) . . ?
N62 C61 C6 114.0(4) . . ?
N62 C61 C611 124.0(4) . . ?
C6 C61 C611 122.0(4) . . ?
C61 N62 N63 120.8(4) . . ?
C61 N62 Cu1 116.1(3) . . ?
N63 N62 Cu1 122.8(3) . . ?
N62 N63 H63A 108(3) . . ?
N62 N63 H63B 114(3) . . ?
H63A N63 H63B 102(4) . . ?
C21 C211 H21A 109.5 . . ?
C21 C211 H21B 109.5 . . ?
H21A C211 H21B 109.5 . . ?
C21 C211 H21C 109.5 . . ?
H21A C211 H21C 109.5 . . ?
H21B C211 H21C 109.5 . . ?
C61 C611 H61A 109.5 . . ?
C61 C611 H61B 109.5 . . ?
H61A C611 H61B 109.5 . . ?
C61 C611 H61C 109.5 . . ?
H61A C611 H61C 109.5 . . ?
H61B C611 H61C 109.5 . . ?
N1B Cu1B N22B 79.25(15) . . ?
N1B Cu1B N62B 78.44(15) . . ?
N22B Cu1B N62B 155.24(15) . . ?
N1B Cu1B Cl2B 165.62(11) . . ?
N22B Cu1B Cl2B 99.84(11) . . ?
N62B Cu1B Cl2B 99.11(11) . . ?
N1B Cu1B Cl3B 94.44(11) . . ?
N22B Cu1B Cl3B 91.27(11) . . ?
N62B Cu1B Cl3B 101.00(11) . . ?
Cl2B Cu1B Cl3B 99.94(4) . . ?
C6B N1B C2B 122.8(4) . . ?
C6B N1B Cu1B 119.2(3) . . ?
C2B N1B Cu1B 117.9(3) . . ?
N1B C2B C3B 120.1(4) . . ?
N1B C2B C21B 113.2(4) . . ?
C3B C2B C21B 126.7(4) . . ?
C2B C3B C4B 117.4(4) . . ?
C2B C3B H3B 121.3 . . ?
C4B C3B H3B 121.3 . . ?
C5B C4B C3B 122.2(4) . . ?
C5B C4B H4B 118.9 . . ?
C3B C4B H4B 118.9 . . ?
C4B C5B C6B 117.2(4) . . ?
C4B C5B H5B 121.4 . . ?
C6B C5B H5B 121.4 . . ?
N1B C6B C5B 120.2(4) . . ?
N1B C6B C61B 112.5(4) . . ?
C5B C6B C61B 127.4(4) . . ?
N22B C21B C2B 113.5(4) . . ?
N22B C21B C22B 125.9(4) . . ?
C2B C21B C22B 120.6(4) . . ?
C21B N22B N23B 123.0(4) . . ?
C21B N22B Cu1B 115.1(3) . . ?
N23B N22B Cu1B 121.6(3) . . ?
N22B N23B H23C 116(3) . . ?
N22B N23B H23D 111(3) . . ?
H23C N23B H23D 131(5) . . ?
N62B C61B C6B 114.1(4) . . ?
N62B C61B C62B 122.5(4) . . ?
C6B C61B C62B 123.4(4) . . ?
C61B N62B N63B 121.5(4) . . ?
C61B N62B Cu1B 115.4(3) . . ?
N63B N62B Cu1B 122.7(3) . . ?
N62B N63B H63C 108(3) . . ?
N62B N63B H63D 116(4) . . ?
H63C N63B H63D 117(5) . . ?
C21B C22B H22A 109.5 . . ?
C21B C22B H22B 109.5 . . ?
H22A C22B H22B 109.5 . . ?
C21B C22B H22C 109.5 . . ?
H22A C22B H22C 109.5 . . ?
H22B C22B H22C 109.5 . . ?
C61B C62B H62A 109.5 . . ?
C61B C62B H62B 109.5 . . ?
H62A C62B H62B 109.5 . . ?
C61B C62B H62C 109.5 . . ?
H62A C62B H62C 109.5 . . ?
H62B C62B H62C 109.5 . . ?
H1O O1 H2O 107(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
N62 Cu1 N1 C6 5.0(3) . . . . ?
N22 Cu1 N1 C6 174.4(3) . . . . ?
Cl2 Cu1 N1 C6 84.5(4) . . . . ?
Cl3 Cu1 N1 C6 -93.2(3) . . . . ?
N62 Cu1 N1 C2 -175.4(3) . . . . ?
N22 Cu1 N1 C2 -5.9(3) . . . . ?
Cl2 Cu1 N1 C2 -95.9(4) . . . . ?
Cl3 Cu1 N1 C2 86.5(3) . . . . ?
C6 N1 C2 C3 2.0(6) . . . . ?
Cu1 N1 C2 C3 -177.7(3) . . . . ?
C6 N1 C2 C21 -176.4(4) . . . . ?
Cu1 N1 C2 C21 3.9(5) . . . . ?
N1 C2 C3 C4 -0.5(7) . . . . ?
C21 C2 C3 C4 177.7(4) . . . . ?
C2 C3 C4 C5 -1.2(7) . . . . ?
C3 C4 C5 C6 1.5(7) . . . . ?
C2 N1 C6 C5 -1.7(6) . . . . ?
Cu1 N1 C6 C5 177.9(3) . . . . ?
C2 N1 C6 C61 175.6(4) . . . . ?
Cu1 N1 C6 C61 -4.8(5) . . . . ?
C4 C5 C6 N1 0.0(6) . . . . ?
C4 C5 C6 C61 -176.9(4) . . . . ?
N1 C2 C21 N22 2.3(6) . . . . ?
C3 C2 C21 N22 -175.9(4) . . . . ?
N1 C2 C21 C211 -178.8(4) . . . . ?
C3 C2 C21 C211 2.9(7) . . . . ?
C2 C21 N22 N23 174.1(4) . . . . ?
C211 C21 N22 N23 -4.7(7) . . . . ?
C2 C21 N22 Cu1 -7.2(5) . . . . ?
C211 C21 N22 Cu1 174.0(3) . . . . ?
N1 Cu1 N22 C21 7.3(3) . . . . ?
N62 Cu1 N22 C21 31.9(5) . . . . ?
Cl2 Cu1 N22 C21 165.3(3) . . . . ?
Cl3 Cu1 N22 C21 -91.8(3) . . . . ?
N1 Cu1 N22 N23 -174.0(4) . . . . ?
N62 Cu1 N22 N23 -149.4(3) . . . . ?
Cl2 Cu1 N22 N23 -16.1(3) . . . . ?
Cl3 Cu1 N22 N23 86.8(3) . . . . ?
N1 C6 C61 N62 0.9(6) . . . . ?
C5 C6 C61 N62 178.0(4) . . . . ?
N1 C6 C61 C611 -178.1(4) . . . . ?
C5 C6 C61 C611 -1.0(7) . . . . ?
C6 C61 N62 N63 177.0(4) . . . . ?
C611 C61 N62 N63 -4.1(7) . . . . ?
C6 C61 N62 Cu1 3.1(5) . . . . ?
C611 C61 N62 Cu1 -178.0(3) . . . . ?
N1 Cu1 N62 C61 -4.4(3) . . . . ?
N22 Cu1 N62 C61 -28.9(5) . . . . ?
Cl2 Cu1 N62 C61 -162.9(3) . . . . ?
Cl3 Cu1 N62 C61 93.8(3) . . . . ?
N1 Cu1 N62 N63 -178.1(4) . . . . ?
N22 Cu1 N62 N63 157.3(3) . . . . ?
Cl2 Cu1 N62 N63 23.3(3) . . . . ?
Cl3 Cu1 N62 N63 -80.0(3) . . . . ?
N22B Cu1B N1B C6B 174.9(3) . . . . ?
N62B Cu1B N1B C6B 5.7(3) . . . . ?
Cl2B Cu1B N1B C6B 87.3(5) . . . . ?
Cl3B Cu1B N1B C6B -94.6(3) . . . . ?
N22B Cu1B N1B C2B -7.5(3) . . . . ?
N62B Cu1B N1B C2B -176.8(3) . . . . ?
Cl2B Cu1B N1B C2B -95.2(5) . . . . ?
Cl3B Cu1B N1B C2B 82.9(3) . . . . ?
C6B N1B C2B C3B 1.3(6) . . . . ?
Cu1B N1B C2B C3B -176.1(3) . . . . ?
C6B N1B C2B C21B -177.4(4) . . . . ?
Cu1B N1B C2B C21B 5.2(5) . . . . ?
N1B C2B C3B C4B 1.0(6) . . . . ?
C21B C2B C3B C4B 179.5(4) . . . . ?
C2B C3B C4B C5B -2.0(7) . . . . ?
C3B C4B C5B C6B 0.8(7) . . . . ?
C2B N1B C6B C5B -2.6(6) . . . . ?
Cu1B N1B C6B C5B 174.7(3) . . . . ?
C2B N1B C6B C61B 177.3(4) . . . . ?
Cu1B N1B C6B C61B -5.3(5) . . . . ?
C4B C5B C6B N1B 1.5(6) . . . . ?
C4B C5B C6B C61B -178.4(4) . . . . ?
N1B C2B C21B N22B 2.7(5) . . . . ?
C3B C2B C21B N22B -175.9(4) . . . . ?
N1B C2B C21B C22B -178.3(4) . . . . ?
C3B C2B C21B C22B 3.0(7) . . . . ?
C2B C21B N22B N23B 177.8(4) . . . . ?
C22B C21B N22B N23B -1.1(7) . . . . ?
C2B C21B N22B Cu1B -8.8(5) . . . . ?
C22B C21B N22B Cu1B 172.3(4) . . . . ?
N1B Cu1B N22B C21B 9.1(3) . . . . ?
N62B Cu1B N22B C21B 35.1(5) . . . . ?
Cl2B Cu1B N22B C21B 174.5(3) . . . . ?
Cl3B Cu1B N22B C21B -85.2(3) . . . . ?
N1B Cu1B N22B N23B -177.3(4) . . . . ?
N62B Cu1B N22B N23B -151.4(4) . . . . ?
Cl2B Cu1B N22B N23B -11.9(4) . . . . ?
Cl3B Cu1B N22B N23B 88.4(3) . . . . ?
N1B C6B C61B N62B 0.6(5) . . . . ?
C5B C6B C61B N62B -179.5(4) . . . . ?
N1B C6B C61B C62B -177.5(4) . . . . ?
C5B C6B C61B C62B 2.5(7) . . . . ?
C6B C61B N62B N63B 176.9(4) . . . . ?
C62B C61B N62B N63B -5.0(7) . . . . ?
C6B C61B N62B Cu1B 3.9(5) . . . . ?
C62B C61B N62B Cu1B -178.0(3) . . . . ?
N1B Cu1B N62B C61B -5.2(3) . . . . ?
N22B Cu1B N62B C61B -31.3(5) . . . . ?
Cl2B Cu1B N62B C61B -170.8(3) . . . . ?
Cl3B Cu1B N62B C61B 87.1(3) . . . . ?
N1B Cu1B N62B N63B -178.1(4) . . . . ?
N22B Cu1B N62B N63B 155.8(4) . . . . ?
Cl2B Cu1B N62B N63B 16.3(3) . . . . ?
Cl3B Cu1B N62B N63B -85.8(3) . . . . ?

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
N23 H23B N63B 0.83(5) 2.49(5) 3.156(6) 139(5) 1_565
N23 H23A Cl3B 0.81(5) 2.59(5) 3.248(4) 140(5) 1_565
N63 H63A Cl3 0.87(5) 2.66(5) 3.180(4) 119(4) 2_545
N63 H63A Cl2 0.87(5) 2.68(5) 3.297(4) 129(4) .
N63 H63B Cl2 0.87(5) 2.74(5) 3.460(4) 141(4) 2_545
N23B H23D Cl2B 0.878(10) 2.65(4) 3.317(5) 133(4) .
N23B H23C Cl3B 0.86(5) 2.49(5) 3.271(4) 150(4) 2_655
N63B H63C Cl2B 0.95(5) 2.60(5) 3.337(5) 134(4) .
N63B H63D N63 0.80(5) 2.37(5) 3.069(6) 148(5) 2_545
O1 H1O Cl3 0.836(9) 2.663(9) 3.489(4) 170(5) 4_676
O1 H2O Cl3B 0.833(10) 2.41(2) 3.214(4) 163(6) 1_565
####################################################################### 
# 
# 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_be87om1n
_database_code_depnum_ccdc_archive 'CCDC 2174283'
loop_
_audit_author_name
_audit_author_address
'Guillermo Zaragoza'
;Unidade de Difraccion de Raios X Edificio CACTUS Universidade de Santiago de Compostela
Spain
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-07-28 downloaded from the CCDC.
;

_audit_creation_date             2012-10-30T10:19:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        CdL'
_chemical_formula_moiety         'C9 H13 Cd1 Cl2 N5'
_chemical_formula_sum            'C9 H13 Cd Cl2 N5'
_chemical_formula_weight         374.54
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.366(2)
_cell_length_b                   14.446(3)
_cell_length_c                   10.650(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.774(4)
_cell_angle_gamma                90
_cell_volume                     1286.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1334
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      28.04
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.19
_exptl_crystal_density_diffrn    1.934
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_absorpt_correction_T_min  0.635
_exptl_absorpt_correction_T_max  1

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Smart-CCD-1000 BRUKER'
_diffrn_measurement_method       'omega scans'
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_number            22962
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_full        27.88
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             3042
_reflns_number_gt                2510
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'DIRDIF96 ( Beurskens, et all 1996)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0238P)²+0.5557P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3042
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.028
_refine_ls_R_factor_gt           0.0211
_refine_ls_wR_factor_ref         0.0542
_refine_ls_wR_factor_gt          0.0522
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.076

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.109389(19) 0.195628(10) 0.037426(14) 0.03206(6) Uani 1 1 d . . .
Cl2 Cl -0.09560(8) 0.29360(4) 0.12379(6) 0.04584(15) Uani 1 1 d . . .
Cl3 Cl 0.31905(8) 0.30305(4) -0.03140(6) 0.04805(15) Uani 1 1 d . . .
N1 N 0.2139(2) 0.05037(12) 0.01207(16) 0.0306(4) Uani 1 1 d . . .
C2 C 0.2947(2) 0.00878(14) 0.1071(2) 0.0317(4) Uani 1 1 d . . .
C3 C 0.3712(3) -0.07527(16) 0.0891(2) 0.0400(5) Uani 1 1 d . . .
H3 H 0.4292 -0.1034 0.1545 0.048 Uiso 1 1 calc R . .
C4 C 0.3592(3) -0.11602(16) -0.0275(2) 0.0431(6) Uani 1 1 d . . .
H4 H 0.4098 -0.1722 -0.0414 0.052 Uiso 1 1 calc R . .
C5 C 0.2725(3) -0.07401(15) -0.1239(2) 0.0393(5) Uani 1 1 d . . .
H5 H 0.2625 -0.102 -0.2024 0.047 Uiso 1 1 calc R . .
C6 C 0.2006(2) 0.01056(14) -0.1019(2) 0.0315(4) Uani 1 1 d . . .
C21 C 0.2923(3) 0.05783(15) 0.2300(2) 0.0338(5) Uani 1 1 d . . .
N22 N 0.1980(2) 0.12732(12) 0.23367(17) 0.0335(4) Uani 1 1 d . . .
N23 N 0.1877(3) 0.17962(16) 0.3411(2) 0.0432(5) Uani 1 1 d . . .
H23A H 0.220(3) 0.157(2) 0.407(3) 0.052 Uiso 1 1 d . . .
H23B H 0.096(4) 0.2020(18) 0.339(3) 0.052 Uiso 1 1 d . . .
C61 C 0.1058(3) 0.06258(15) -0.1984(2) 0.0325(5) Uani 1 1 d . . .
N62 N 0.0321(2) 0.13475(13) -0.15921(17) 0.0368(4) Uani 1 1 d . . .
N63 N -0.0508(3) 0.19019(18) -0.2409(2) 0.0569(7) Uani 1 1 d . . .
H63A H -0.120(4) 0.225(2) -0.200(3) 0.068 Uiso 1 1 d . . .
H63B H -0.065(4) 0.171(2) -0.311(3) 0.068 Uiso 1 1 d . . .
C211 C 0.3914(3) 0.0243(2) 0.3405(2) 0.0539(7) Uani 1 1 d . . .
H21A H 0.4494 0.0753 0.3775 0.081 Uiso 1 1 calc R . .
H21B H 0.4654 -0.0218 0.3133 0.081 Uiso 1 1 calc R . .
H21C H 0.3228 -0.0022 0.4016 0.081 Uiso 1 1 calc R . .
C611 C 0.0996(3) 0.03166(17) -0.3325(2) 0.0432(6) Uani 1 1 d . . .
H61A H -0.0077 0.0136 -0.3558 0.065 Uiso 1 1 calc R . .
H61B H 0.1702 -0.02 -0.3423 0.065 Uiso 1 1 calc R . .
H61C H 0.1322 0.0816 -0.3853 0.065 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Cd1 N1 2.2926(17) . ?
Cd1 N62 2.3437(19) . ?
Cd1 N22 2.4072(18) . ?
Cd1 Cl2 2.4264(7) . ?
Cd1 Cl3 2.4701(7) . ?
N1 C2 1.342(3) . ?
N1 C6 1.344(3) . ?
C2 C3 1.388(3) . ?
C2 C21 1.489(3) . ?
C3 C4 1.375(3) . ?
C3 H3 0.93 . ?
C4 C5 1.379(3) . ?
C4 H4 0.93 . ?
C5 C6 1.385(3) . ?
C5 H5 0.93 . ?
C6 C61 1.483(3) . ?
C21 N22 1.279(3) . ?
C21 C211 1.499(3) . ?
N22 N23 1.376(3) . ?
N23 H23A 0.81(3) . ?
N23 H23B 0.83(3) . ?
C61 N62 1.287(3) . ?
C61 C611 1.495(3) . ?
N62 N63 1.357(3) . ?
N63 H63A 0.89(3) . ?
N63 H63B 0.80(3) . ?
C211 H21A 0.96 . ?
C211 H21B 0.96 . ?
C211 H21C 0.96 . ?
C611 H61A 0.96 . ?
C611 H61B 0.96 . ?
C611 H61C 0.96 . ?

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
N1 Cd1 N62 69.32(6) . . ?
N1 Cd1 N22 67.59(6) . . ?
N62 Cd1 N22 133.70(7) . . ?
N1 Cd1 Cl2 148.78(4) . . ?
N62 Cd1 Cl2 112.27(5) . . ?
N22 Cd1 Cl2 96.44(5) . . ?
N1 Cd1 Cl3 105.25(5) . . ?
N62 Cd1 Cl3 98.58(5) . . ?
N22 Cd1 Cl3 108.23(5) . . ?
Cl2 Cd1 Cl3 105.23(3) . . ?
C2 N1 C6 121.02(18) . . ?
C2 N1 Cd1 120.40(14) . . ?
C6 N1 Cd1 118.46(14) . . ?
N1 C2 C3 120.7(2) . . ?
N1 C2 C21 115.46(18) . . ?
C3 C2 C21 123.8(2) . . ?
C4 C3 C2 118.6(2) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 118.9(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
N1 C6 C5 120.4(2) . . ?
N1 C6 C61 115.89(18) . . ?
C5 C6 C61 123.7(2) . . ?
N22 C21 C2 115.20(19) . . ?
N22 C21 C211 123.8(2) . . ?
C2 C21 C211 120.9(2) . . ?
C21 N22 N23 120.7(2) . . ?
C21 N22 Cd1 117.96(14) . . ?
N23 N22 Cd1 118.13(15) . . ?
N22 N23 H23A 118(2) . . ?
N22 N23 H23B 106(2) . . ?
H23A N23 H23B 117(3) . . ?
N62 C61 C6 115.88(19) . . ?
N62 C61 C611 123.3(2) . . ?
C6 C61 C611 120.84(19) . . ?
C61 N62 N63 120.7(2) . . ?
C61 N62 Cd1 118.18(15) . . ?
N63 N62 Cd1 118.19(16) . . ?
N62 N63 H63A 110(2) . . ?
N62 N63 H63B 117(2) . . ?
H63A N63 H63B 125(3) . . ?
C21 C211 H21A 109.5 . . ?
C21 C211 H21B 109.5 . . ?
H21A C211 H21B 109.5 . . ?
C21 C211 H21C 109.5 . . ?
H21A C211 H21C 109.5 . . ?
H21B C211 H21C 109.5 . . ?
C61 C611 H61A 109.5 . . ?
C61 C611 H61B 109.5 . . ?
H61A C611 H61B 109.5 . . ?
C61 C611 H61C 109.5 . . ?
H61A C611 H61C 109.5 . . ?
H61B C611 H61C 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
N62 Cd1 N1 C2 -174.60(17) . . . . ?
N22 Cd1 N1 C2 -11.97(14) . . . . ?
Cl2 Cd1 N1 C2 -75.46(18) . . . . ?
Cl3 Cd1 N1 C2 91.82(15) . . . . ?
N62 Cd1 N1 C6 9.31(14) . . . . ?
N22 Cd1 N1 C6 171.94(16) . . . . ?
Cl2 Cd1 N1 C6 108.45(15) . . . . ?
Cl3 Cd1 N1 C6 -84.27(15) . . . . ?
C6 N1 C2 C3 2.1(3) . . . . ?
Cd1 N1 C2 C3 -173.88(15) . . . . ?
C6 N1 C2 C21 -176.66(18) . . . . ?
Cd1 N1 C2 C21 7.4(2) . . . . ?
N1 C2 C3 C4 -1.5(3) . . . . ?
C21 C2 C3 C4 177.2(2) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C2 N1 C6 C5 -1.0(3) . . . . ?
Cd1 N1 C6 C5 175.06(15) . . . . ?
C2 N1 C6 C61 178.89(18) . . . . ?
Cd1 N1 C6 C61 -5.0(2) . . . . ?
C4 C5 C6 N1 -0.7(3) . . . . ?
C4 C5 C6 C61 179.4(2) . . . . ?
N1 C2 C21 N22 8.2(3) . . . . ?
C3 C2 C21 N22 -170.5(2) . . . . ?
N1 C2 C21 C211 -173.6(2) . . . . ?
C3 C2 C21 C211 7.6(3) . . . . ?
C2 C21 N22 N23 -178.55(19) . . . . ?
C211 C21 N22 N23 3.3(3) . . . . ?
C2 C21 N22 Cd1 -19.0(2) . . . . ?
C211 C21 N22 Cd1 162.88(19) . . . . ?
N1 Cd1 N22 C21 16.79(15) . . . . ?
N62 Cd1 N22 C21 39.51(19) . . . . ?
Cl2 Cd1 N22 C21 168.97(15) . . . . ?
Cl3 Cd1 N22 C21 -82.64(16) . . . . ?
N1 Cd1 N22 N23 176.86(18) . . . . ?
N62 Cd1 N22 N23 -160.42(15) . . . . ?
Cl2 Cd1 N22 N23 -30.97(16) . . . . ?
Cl3 Cd1 N22 N23 77.43(16) . . . . ?
N1 C6 C61 N62 -7.4(3) . . . . ?
C5 C6 C61 N62 172.5(2) . . . . ?
N1 C6 C61 C611 172.17(19) . . . . ?
C5 C6 C61 C611 -7.9(3) . . . . ?
C6 C61 N62 N63 176.4(2) . . . . ?
C611 C61 N62 N63 -3.2(3) . . . . ?
C6 C61 N62 Cd1 16.1(2) . . . . ?
C611 C61 N62 Cd1 -163.51(17) . . . . ?
N1 Cd1 N62 C61 -13.76(15) . . . . ?
N22 Cd1 N62 C61 -36.2(2) . . . . ?
Cl2 Cd1 N62 C61 -160.19(15) . . . . ?
Cl3 Cd1 N62 C61 89.38(16) . . . . ?
N1 Cd1 N62 N63 -174.6(2) . . . . ?
N22 Cd1 N62 N63 162.99(17) . . . . ?
Cl2 Cd1 N62 N63 39.0(2) . . . . ?
Cl3 Cd1 N62 N63 -71.43(19) . . . . ?

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
N23 H23A Cl2 0.81(3) 2.83(3) 3.487(2) 139(3) 4_666
N23 H23B Cl3 0.83(3) 2.73(3) 3.417(3) 141(2) 4_566
N63 H63B Cl3 0.80(3) 2.54(3) 3.250(2) 149(3) 4_565
N63 H63A N23 0.89(3) 2.17(3) 3.034(3) 162(3) 4_565
