# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_h2nca1
_database_code_depnum_ccdc_archive 'CCDC 2048073'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2020-12-03 deposited with the CCDC.	2021-02-25 downloaded from the CCDC.
;

_audit_creation_date             2019-10-21T11:51:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum            'C6 H7 Cl N Na O9'
_chemical_formula_weight         295.64

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   6.712(5)
_cell_length_b                   8.686(4)
_cell_length_c                   9.824(2)
_cell_angle_alpha                74.65(3)
_cell_angle_beta                 75.32(5)
_cell_angle_gamma                86.21(5)
_cell_volume                     534.3(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9.40
_cell_measurement_theta_max      15.89
_cell_measurement_temperature    293(2)
_exptl_crystal_description       rod
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_exptl_crystal_colour            'light red'
_exptl_crystal_density_diffrn    1.831
_exptl_crystal_F_000             298
_exptl_absorpt_coefficient_mu    0.441
_exptl_absorpt_correction_type   none

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled ω/2τ scans'
_diffrn_reflns_number            2061
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_theta_min         2.218
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_full        25.005
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_standards_number         3
_diffrn_standards_interval_time  60
_diffrn_standards_decay_%        11
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 -1 0
2 2 1
0 -4 -2


#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   mixed

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             1884
_reflns_number_gt                1434
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1149
_refine_ls_R_factor_gt           0.0871
_refine_ls_wR_factor_ref         0.2439
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.064
_refine_ls_number_reflns         1884
_refine_ls_number_parameters     181
_refine_ls_number_restraints     15
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1830P)²+0.2843P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.019
_refine_diff_density_min         -0.906
_refine_diff_density_rms         0.19
_refine_ls_extinction_method     none
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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 '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'

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Na1 0.2137(4) 0.5684(2) 0.2206(2) 0.0357(6) Uani d 1 . . Na
Cl1 0.2583(2) 0.08915(14) 0.69294(13) 0.0301(5) Uani d 1 . . Cl
O1 0.2574(6) 0.3412(4) 0.4180(4) 0.0337(10) Uani d 1 . . O
O2 0.2434(7) 0.3078(4) 0.1626(4) 0.0409(11) Uani d 1 . . O
O3 0.2199(6) -0.2532(4) 0.3652(4) 0.0328(9) Uani d 1 . . O
O4 0.2344(6) -0.2095(4) 0.6163(4) 0.0332(9) Uani d 1 . . O
H4 0.228328 -0.289969 0.588795 0.05 Uiso calc 1 . . H
O5 0.1961(8) 0.1082(5) 0.0106(4) 0.0461(11) Uani d 1 . . O
O6 0.3080(8) -0.1283(5) 0.0781(4) 0.0500(12) Uani d 1 . . O
N1 0.2484(7) 0.0002(5) 0.1032(4) 0.0263(10) Uani d 1 . . N
C1 0.2540(7) 0.2043(5) 0.4063(5) 0.0218(10) Uani d 1 . . C
C2 0.2463(8) 0.1822(5) 0.2576(5) 0.0248(11) Uani d 1 . . C
C3 0.2454(7) 0.0248(5) 0.2414(5) 0.0219(10) Uani d 1 . . C
C4 0.2381(7) -0.1120(5) 0.3625(5) 0.0223(10) Uani d 1 . . C
C5 0.2441(7) -0.0826(5) 0.5063(5) 0.0219(10) Uani d 1 . . C
C6 0.2536(7) 0.0650(5) 0.5249(5) 0.0223(10) Uani d 1 . . C
O7 -0.1638(7) 0.5127(4) 0.3446(4) 0.0384(10) Uani d 1 . . O
H7A -0.232(8) 0.569(6) 0.275(5) 0.046 Uiso d 1 . . H
H7B -0.204(6) 0.571(4) 0.416(4) 0.046 Uiso d 1 . . H
O8 0.5845(7) 0.5747(5) 0.1490(4) 0.0426(11) Uani d 1 . . O
H8A 0.647(6) 0.665(4) 0.077(5) 0.051 Uiso d 1 . . H
H8B 0.622(8) 0.494(5) 0.097(5) 0.051 Uiso d 1 . . H
O9 0.1472(8) 0.6491(5) -0.0277(5) 0.0491(11) Uani d 1 . . O
H9A 0.188(7) 0.758(3) -0.074(4) 0.059 Uiso d 1 . . H
H9B 0.019(6) 0.649(7) -0.052(8) 0.059 Uiso d 1 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Na1 O3 1_565 2.372(4) ?
Na1 O8 . 2.409(5) ?
Na1 O1 . 2.434(4) ?
Na1 O2 . 2.460(4) ?
Na1 O9 . 2.499(5) ?
Na1 O7 . 2.535(5) ?
Na1 O6 1_565 2.669(5) ?
Cl1 C6 . 1.727(5) ?
O1 C1 . 1.227(6) ?
O2 C2 . 1.236(6) ?
O3 C4 . 1.233(5) ?
O4 C5 . 1.315(6) ?
O4 H4 . 0.82 ?
O5 N1 . 1.223(6) ?
O6 N1 . 1.226(6) ?
N1 C3 . 1.424(6) ?
C1 C6 . 1.440(7) ?
C1 C2 . 1.536(7) ?
C2 C3 . 1.418(6) ?
C3 C4 . 1.435(7) ?
C4 C5 . 1.511(7) ?
C5 C6 . 1.350(6) ?
O7 H7A . 0.936(19) ?
O7 H7B . 0.949(18) ?
O8 H8A . 0.943(19) ?
O8 H8B . 0.959(19) ?
O9 H9A . 0.957(19) ?
O9 H9B . 0.95(2) ?

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
O3 Na1 O8 89.35(15) 1_565 . ?
O3 Na1 O1 90.86(14) 1_565 . ?
O8 Na1 O1 85.09(16) . . ?
O3 Na1 O2 155.58(16) 1_565 . ?
O8 Na1 O2 85.93(16) . . ?
O1 Na1 O2 64.88(13) . . ?
O3 Na1 O9 124.58(16) 1_565 . ?
O8 Na1 O9 98.29(17) . . ?
O1 Na1 O9 144.28(15) . . ?
O2 Na1 O9 79.83(15) . . ?
O3 Na1 O7 89.68(14) 1_565 . ?
O8 Na1 O7 167.06(16) . . ?
O1 Na1 O7 82.02(16) . . ?
O2 Na1 O7 89.64(15) . . ?
O9 Na1 O7 92.87(17) . . ?
O3 Na1 O6 63.52(12) 1_565 1_565 ?
O8 Na1 O6 75.28(17) . 1_565 ?
O1 Na1 O6 147.33(16) . 1_565 ?
O2 Na1 O6 137.25(15) . 1_565 ?
O9 Na1 O6 65.77(15) . 1_565 ?
O7 Na1 O6 115.61(17) . 1_565 ?
C1 O1 Na1 120.7(3) . . ?
C2 O2 Na1 121.2(3) . . ?
C4 O3 Na1 144.4(3) . 1_545 ?
C5 O4 H4 109.5 . . ?
N1 O6 Na1 133.7(3) . 1_545 ?
O5 N1 O6 121.1(4) . . ?
O5 N1 C3 119.7(4) . . ?
O6 N1 C3 119.2(4) . . ?
O1 C1 C6 123.3(4) . . ?
O1 C1 C2 117.7(4) . . ?
C6 C1 C2 118.9(4) . . ?
O2 C2 C3 126.7(5) . . ?
O2 C2 C1 114.8(4) . . ?
C3 C2 C1 118.5(4) . . ?
C2 C3 N1 119.9(4) . . ?
C2 C3 C4 121.4(4) . . ?
N1 C3 C4 118.7(4) . . ?
O3 C4 C3 127.5(5) . . ?
O3 C4 C5 115.0(4) . . ?
C3 C4 C5 117.5(4) . . ?
O4 C5 C6 120.6(4) . . ?
O4 C5 C4 116.5(4) . . ?
C6 C5 C4 122.9(4) . . ?
C5 C6 C1 120.6(4) . . ?
C5 C6 Cl1 120.3(4) . . ?
C1 C6 Cl1 119.1(3) . . ?
Na1 O7 H7A 104(4) . . ?
Na1 O7 H7B 108(2) . . ?
H7A O7 H7B 101(3) . . ?
Na1 O8 H8A 117(3) . . ?
Na1 O8 H8B 105(3) . . ?
H8A O8 H8B 100(3) . . ?
Na1 O9 H9A 110(3) . . ?
Na1 O9 H9B 127(4) . . ?
H9A O9 H9B 100(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Na1 O6 N1 O5 -131.2(4) 1_545 . . . ?
Na1 O6 N1 C3 50.4(7) 1_545 . . . ?
Na1 O1 C1 C6 -172.1(4) . . . . ?
Na1 O1 C1 C2 6.8(6) . . . . ?
Na1 O2 C2 C3 174.3(4) . . . . ?
Na1 O2 C2 C1 -6.4(6) . . . . ?
O1 C1 C2 O2 -0.3(7) . . . . ?
C6 C1 C2 O2 178.8(4) . . . . ?
O1 C1 C2 C3 179.1(4) . . . . ?
C6 C1 C2 C3 -1.9(7) . . . . ?
O2 C2 C3 N1 2.3(8) . . . . ?
C1 C2 C3 N1 -177.0(4) . . . . ?
O2 C2 C3 C4 -176.7(5) . . . . ?
C1 C2 C3 C4 4.1(7) . . . . ?
O5 N1 C3 C2 -19.8(7) . . . . ?
O6 N1 C3 C2 158.6(5) . . . . ?
O5 N1 C3 C4 159.2(5) . . . . ?
O6 N1 C3 C4 -22.4(7) . . . . ?
Na1 O3 C4 C3 7.9(9) 1_545 . . . ?
Na1 O3 C4 C5 -174.9(4) 1_545 . . . ?
C2 C3 C4 O3 173.6(5) . . . . ?
N1 C3 C4 O3 -5.4(8) . . . . ?
C2 C3 C4 C5 -3.5(7) . . . . ?
N1 C3 C4 C5 177.5(4) . . . . ?
O3 C4 C5 O4 1.6(7) . . . . ?
C3 C4 C5 O4 179.1(4) . . . . ?
O3 C4 C5 C6 -176.8(5) . . . . ?
C3 C4 C5 C6 0.7(7) . . . . ?
O4 C5 C6 C1 -176.9(4) . . . . ?
C4 C5 C6 C1 1.4(8) . . . . ?
O4 C5 C6 Cl1 1.3(7) . . . . ?
C4 C5 C6 Cl1 179.6(3) . . . . ?
O1 C1 C6 C5 178.2(5) . . . . ?
C2 C1 C6 C5 -0.8(7) . . . . ?
O1 C1 C6 Cl1 0.0(7) . . . . ?
C2 C1 C6 Cl1 -179.0(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
_geom_hbond_publ_flag
O4 H4 O3 0.82 2.15 2.619(5) 116.4 . yes
O4 H4 O7 0.82 1.91 2.616(5) 143.4 2_556 yes
O7 H7A O8 0.936(19) 1.94(3) 2.795(6) 151(5) 1_455 yes
O7 H7B O3 0.949(18) 3.00(4) 3.085(5) 86(3) 2_556 yes
O8 H8A O2 0.943(19) 2.23(5) 2.908(5) 128(4) 2_665 yes
O8 H8A O5 0.943(19) 2.16(3) 3.049(6) 157(5) 2_665 yes
O8 H8B O9 0.959(19) 2.01(4) 2.849(6) 144(4) 2_665 yes
O9 H9B O2 0.95(2) 2.26(3) 3.184(7) 165(5) 2_565 yes
O9 H9B O5 0.95(2) 2.54(6) 3.022(7) 111(4) 2_565 yes



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_s214
_database_code_depnum_ccdc_archive 'CCDC 2048075'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2020-12-03 deposited with the CCDC.	2021-02-25 downloaded from the CCDC.
;

_audit_creation_date             2019-10-21T16:06:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum            'C6 H4 Cl K2 N O8'
_chemical_formula_weight         331.75

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   9.99890(10)
_cell_length_b                   6.67120(10)
_cell_length_c                   16.8714(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.7540(10)
_cell_angle_gamma                90
_cell_volume                     1077.63(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5039
_cell_measurement_theta_min      4.645
_cell_measurement_theta_max      76.313
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.045
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    10.463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.15475
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            8681
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_theta_min         4.64
_diffrn_reflns_theta_max         76.503
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   difmap

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             2240
_reflns_number_gt                2068
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1091
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.078
_refine_ls_number_reflns         2240
_refine_ls_number_parameters     175
_refine_ls_number_restraints     7
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0615P)²+0.5977P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
K K 0.3868 1.0657 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
K1 0.62032(5) -0.01977(9) 0.26689(3) 0.03733(17) Uani d 1 . . K
K2 0.18762(6) 0.13843(14) 0.14366(4) 0.0620(2) Uani d 1 . . K
Cl1 0.21965(5) 0.25637(8) -0.03392(3) 0.03412(17) Uani d 1 . . Cl
O1 0.44310(18) 0.1431(3) 0.11997(10) 0.0353(4) Uani d 1 . . O
O2 0.71673(17) 0.1524(3) 0.14606(9) 0.0326(4) Uani d 1 . . O
O3 0.6459(2) 0.3511(4) -0.13212(12) 0.0591(6) Uani d 1 . . O
O4 0.37538(19) 0.3496(3) -0.15500(10) 0.0395(4) Uani d 1 . . O
O5 0.92302(19) 0.2854(3) 0.08911(11) 0.0444(4) Uani d 1 . . O
O6 0.8912(2) 0.2009(4) -0.03759(12) 0.0489(5) Uani d 1 . . O
N1 0.8452(2) 0.2451(3) 0.02006(11) 0.0300(4) Uani d 1 . . N
C1 0.4855(2) 0.1975(3) 0.06065(13) 0.0261(4) Uani d 1 . . C
C2 0.6455(2) 0.1996(3) 0.07590(12) 0.0254(4) Uani d 1 . . C
C3 0.6975(2) 0.2481(3) 0.00761(13) 0.0265(4) Uani d 1 . . C
C4 0.6085(2) 0.2993(4) -0.07164(14) 0.0315(5) Uani d 1 . . C
C5 0.4490(2) 0.3028(3) -0.08473(13) 0.0278(4) Uani d 1 . . C
C6 0.3998(2) 0.2540(3) -0.01741(13) 0.0268(4) Uani d 1 . . C
O7 0.5133(3) 0.4464(4) 0.28328(12) 0.0569(6) Uani d 1 . . O
H7A 0.595(3) 0.503(6) 0.316(2) 0.068 Uiso d 1 . . H
H7B 0.501(4) 0.499(6) 0.2305(13) 0.068 Uiso d 1 . . H
O8 0.3627(3) 0.1043(4) 0.29682(14) 0.0596(6) Uani d 1 . . O
H8A 0.427(4) 0.200(5) 0.320(2) 0.071 Uiso d 1 . . H
H8B 0.345(5) 0.008(5) 0.331(2) 0.071 Uiso d 1 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
K1 O2 . 2.7454(17) ?
K1 O1 . 2.8163(17) ?
K1 O8 . 2.885(2) ?
K1 O7 . 3.326(3) ?
K1 K2 . 4.3553(8) ?
K1 H8A . 2.77(5) ?
K2 O8 . 2.681(2) ?
K2 O1 . 2.6971(18) ?
K2 Cl1 . 3.2018(9) ?
K2 O8 2 3.348(3) ?
K2 K2 2 4.7934(9) ?
Cl1 C6 . 1.741(2) ?
O1 C1 . 1.248(3) ?
O2 C2 . 1.234(3) ?
O3 C4 . 1.233(3) ?
O4 C5 . 1.242(3) ?
O5 N1 . 1.230(3) ?
O6 N1 . 1.226(3) ?
N1 C3 . 1.431(3) ?
C1 C6 . 1.400(3) ?
C1 C2 . 1.546(3) ?
C2 C3 . 1.431(3) ?
C3 C4 . 1.418(3) ?
C4 C5 . 1.546(3) ?
C5 C6 . 1.400(3) ?
O7 H7A . 0.924(18) ?
O7 H7B . 0.932(18) ?
O8 H8A . 0.909(18) ?
O8 H8B . 0.908(18) ?

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
O2 K1 O1 56.75(5) . . ?
O2 K1 O8 122.15(7) . . ?
O1 K1 O8 71.12(6) . . ?
O2 K1 O7 82.00(5) . . ?
O1 K1 O7 64.95(5) . . ?
O8 K1 O7 52.58(7) . . ?
O2 K1 K2 93.28(4) . . ?
O1 K1 K2 36.87(4) . . ?
O8 K1 K2 36.86(5) . . ?
O7 K1 K2 60.92(4) . . ?
O2 K1 H8A 116.3(7) . . ?
O1 K1 H8A 76.0(7) . . ?
O8 K1 H8A 18.3(4) . . ?
O7 K1 H8A 37.5(5) . . ?
K2 K1 H8A 48.3(6) . . ?
O8 K2 O1 76.15(6) . . ?
O8 K2 Cl1 135.17(6) . . ?
O1 K2 Cl1 60.27(4) . . ?
O8 K2 O8 84.41(7) . 2 ?
O1 K2 O8 105.33(6) . 2 ?
Cl1 K2 O8 96.70(4) . 2 ?
O8 K2 K1 40.22(5) . . ?
O1 K2 K1 38.79(4) . . ?
Cl1 K2 K1 98.782(18) . . ?
O8 K2 K1 107.23(5) 2 . ?
O8 K2 K1 92.30(5) . 2 ?
O1 K2 K1 145.62(5) . 2 ?
Cl1 K2 K1 117.32(2) . 2 ?
O8 K2 K1 40.63(4) 2 2 ?
K1 K2 K1 130.865(18) . 2 ?
O8 K2 K2 51.74(6) . 2 ?
O1 K2 K2 92.85(5) . 2 ?
Cl1 K2 K2 117.05(2) . 2 ?
O8 K2 K2 32.73(4) 2 2 ?
K1 K2 K2 78.64(2) . 2 ?
K1 K2 K2 56.180(14) 2 2 ?
C6 Cl1 K2 103.05(8) . . ?
C1 O1 K2 132.62(14) . . ?
C1 O1 K1 123.03(14) . . ?
K2 O1 K1 104.34(6) . . ?
C2 O2 K1 126.16(14) . . ?
O6 N1 O5 121.6(2) . . ?
O6 N1 C3 119.64(19) . . ?
O5 N1 C3 118.72(19) . . ?
O1 C1 C6 125.1(2) . . ?
O1 C1 C2 116.33(18) . . ?
C6 C1 C2 118.53(18) . . ?
O2 C2 C3 125.9(2) . . ?
O2 C2 C1 116.18(18) . . ?
C3 C2 C1 117.85(18) . . ?
C4 C3 N1 118.87(19) . . ?
C4 C3 C2 122.6(2) . . ?
N1 C3 C2 118.55(18) . . ?
O3 C4 C3 126.2(2) . . ?
O3 C4 C5 115.1(2) . . ?
C3 C4 C5 118.67(19) . . ?
O4 C5 C6 125.7(2) . . ?
O4 C5 C4 116.3(2) . . ?
C6 C5 C4 118.03(19) . . ?
C1 C6 C5 124.3(2) . . ?
C1 C6 Cl1 118.51(17) . . ?
C5 C6 Cl1 117.21(16) . . ?
K2 O7 K1 135.90(8) 2 . ?
K2 O7 H7A 100(3) 2 . ?
K1 O7 H7A 100(3) . . ?
K2 O7 H7B 109(3) 2 . ?
K1 O7 H7B 103(3) . . ?
H7A O7 H7B 106(3) . . ?
K2 O8 K1 102.92(7) . . ?
K2 O8 H8A 122(2) . . ?
K1 O8 H8A 74(3) . . ?
K2 O8 H8B 118(3) . . ?
K1 O8 H8B 105(3) . . ?
H8A O8 H8B 118(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
K2 O6 N1 O5 130.2(2) 3_655 . . . ?
K2 O6 N1 C3 -49.1(3) 3_655 . . . ?
K2 O5 N1 O6 -26.4(3) 1_655 . . . ?
K1 O5 N1 O6 163.81(18) 2_655 . . . ?
K2 O5 N1 C3 152.90(15) 1_655 . . . ?
K1 O5 N1 C3 -16.9(3) 2_655 . . . ?
K2 O1 C1 C6 -7.8(3) . . . . ?
K1 O1 C1 C6 171.02(16) . . . . ?
K2 O1 C1 C2 172.75(13) . . . . ?
K1 O1 C1 C2 -8.4(3) . . . . ?
K1 O2 C2 C3 -165.52(16) . . . . ?
K1 O2 C2 C3 68.9(2) 2_655 . . . ?
K1 O2 C2 C1 12.0(3) . . . . ?
K1 O2 C2 C1 -113.59(16) 2_655 . . . ?
K1 O2 C2 K1 125.57(18) . . . 2_655 ?
O1 C1 C2 O2 -1.9(3) . . . . ?
C6 C1 C2 O2 178.7(2) . . . . ?
O1 C1 C2 C3 175.84(19) . . . . ?
C6 C1 C2 C3 -3.6(3) . . . . ?
O1 C1 C2 K1 -58.1(2) . . . 2_655 ?
C6 C1 C2 K1 122.45(17) . . . 2_655 ?
O6 N1 C3 C4 -31.1(3) . . . . ?
O5 N1 C3 C4 149.6(2) . . . . ?
O6 N1 C3 C2 149.1(2) . . . . ?
O5 N1 C3 C2 -30.3(3) . . . . ?
O2 C2 C3 C4 179.4(2) . . . . ?
C1 C2 C3 C4 1.9(3) . . . . ?
K1 C2 C3 C4 -135.32(19) 2_655 . . . ?
O2 C2 C3 N1 -0.7(3) . . . . ?
C1 C2 C3 N1 -178.21(18) . . . . ?
K1 C2 C3 N1 44.5(2) 2_655 . . . ?
N1 C3 C4 O3 -3.2(4) . . . . ?
C2 C3 C4 O3 176.6(3) . . . . ?
N1 C3 C4 C5 -179.89(19) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
K1 O4 C5 C6 -108.3(2) 3_655 . . . ?
K1 O4 C5 C4 71.8(2) 3_655 . . . ?
O3 C4 C5 O4 2.6(3) . . . . ?
C3 C4 C5 O4 179.6(2) . . . . ?
O3 C4 C5 C6 -177.3(2) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
O3 C4 C5 K1 51.2(2) . . . 3_655 ?
C3 C4 C5 K1 -131.81(19) . . . 3_655 ?
O1 C1 C6 C5 -175.9(2) . . . . ?
C2 C1 C6 C5 3.5(3) . . . . ?
O1 C1 C6 Cl1 1.9(3) . . . . ?
C2 C1 C6 Cl1 -178.75(15) . . . . ?
O4 C5 C6 C1 178.5(2) . . . . ?
C4 C5 C6 C1 -1.6(3) . . . . ?
K1 C5 C6 C1 114.0(2) 3_655 . . . ?
O4 C5 C6 Cl1 0.8(3) . . . . ?
C4 C5 C6 Cl1 -179.34(16) . . . . ?
K1 C5 C6 Cl1 -63.8(2) 3_655 . . . ?
K2 Cl1 C6 C1 2.80(18) . . . . ?
K2 Cl1 C6 C5 -179.30(15) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_s351
_database_code_depnum_ccdc_archive 'CCDC 2048076'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2020-12-03 deposited with the CCDC.	2021-02-25 downloaded from the CCDC.
;

_audit_creation_date             2019-11-14T14:18:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_moiety         'C26 H16 Cl N5 Ni O6, C2 H6 O'
_chemical_formula_sum            'C28 H22 Cl N5 Ni O7'
_chemical_formula_weight         634.65

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+z
_cell_length_a                   12.0573(2)
_cell_length_b                   15.8386(2)
_cell_length_c                   15.0458(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.1710(10)
_cell_angle_gamma                90
_cell_volume                     2759.62(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4851
_cell_measurement_theta_min      4.732
_cell_measurement_theta_max      75.942
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    2.395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.13567
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            7031
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_theta_min         4.73
_diffrn_reflns_theta_max         76.487
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       18

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             2852
_reflns_number_gt                2675
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1669
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.185
_refine_ls_number_reflns         2852
_refine_ls_number_parameters     208
_refine_ls_number_restraints     7
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1029P)²+1.5535P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.771
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
Ni Ni -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Ni1 0.5 0.54582(3) 0.75 0.0528(2) Uani d 1 . . Ni
Cl1 0.3493(5) 0.7964(4) 0.8919(4) 0.0997(16) Uani d 0.5 . . Cl
O1 0.43843(18) 0.64670(12) 0.80938(12) 0.0658(5) Uani d 1 . . O
O2 0.4309(2) 0.94283(14) 0.8071(2) 0.0997(9) Uani d 1 . . O
O3 0.2768(6) 0.7592(7) 0.8621(5) 0.136(3) Uani d 0.5 . . O
O4 0.4074(6) 0.8261(5) 0.9595(4) 0.1169(19) Uani d 0.5 . . O
N1 0.3707(13) 0.7964(8) 0.8851(10) 0.072(4) Uani d 0.5 . . N
N2 0.54957(18) 0.45587(12) 0.66834(13) 0.0545(4) Uani d 1 . . N
N3 0.35239(19) 0.53775(13) 0.63911(14) 0.0588(5) Uani d 1 . . N
C1 0.4642(2) 0.71823(16) 0.78508(15) 0.0597(6) Uani d 1 . . C
C2 0.4628(2) 0.87399(18) 0.7843(2) 0.0749(7) Uani d 1 . . C
C3 0.4345(2) 0.79526(18) 0.81584(19) 0.0683(6) Uani d 1 . . C
C4 0.6513(2) 0.41665(19) 0.68715(18) 0.0660(6) Uani d 1 . . C
H4 0.707648 0.430898 0.74112 0.079 Uiso calc 1 . . H
C5 0.6767(3) 0.3558(2) 0.6301(2) 0.0780(8) Uani d 1 . . C
H5 0.748134 0.329073 0.645733 0.094 Uiso calc 1 . . H
C6 0.5937(3) 0.3356(2) 0.5493(2) 0.0829(8) Uani d 1 . . C
H6 0.608585 0.295335 0.509154 0.099 Uiso calc 1 . . H
C7 0.4890(3) 0.37590(18) 0.52928(18) 0.0733(7) Uani d 1 . . C
H7 0.432047 0.363218 0.475058 0.088 Uiso calc 1 . . H
C8 0.4682(2) 0.43561(15) 0.59017(15) 0.0561(5) Uani d 1 . . C
C9 0.3575(2) 0.48180(16) 0.57397(15) 0.0589(5) Uani d 1 . . C
C10 0.2643(3) 0.4688(2) 0.4963(2) 0.0781(8) Uani d 1 . . C
H10 0.26905 0.429132 0.451972 0.094 Uiso calc 1 . . H
C11 0.1650(3) 0.5153(3) 0.4859(3) 0.0896(10) Uani d 1 . . C
H11 0.101939 0.507496 0.434441 0.107 Uiso calc 1 . . H
C12 0.1606(3) 0.5734(3) 0.5528(3) 0.0881(10) Uani d 1 . . C
H12 0.094701 0.60599 0.546741 0.106 Uiso calc 1 . . H
C13 0.2557(2) 0.5829(2) 0.6294(2) 0.0742(7) Uani d 1 . . C
H13 0.252149 0.621501 0.675076 0.089 Uiso calc 1 . . H
O5 0.1099(10) 0.5956(7) 0.7798(9) 0.201(3) Uani d 0.5 . . O
H5O 0.161367 0.626365 0.772569 0.301 Uiso calc 0.5 . . H
C14 0.0249(15) 0.6444(9) 0.8011(12) 0.201(3) Uani d 0.5 . . C
H14A 0.048915 0.657107 0.86678 0.241 Uiso calc 0.5 . . H
H14B -0.045607 0.61154 0.788828 0.241 Uiso calc 0.5 . . H
C15 0 0.7233(8) 0.75 0.201(3) Uani d 1 . . C
H15A -0.059165 0.753349 0.768416 0.301 Uiso calc 0.5 . . H
H15B 0.068691 0.757203 0.762951 0.301 Uiso calc 0.5 . . H
H15C -0.025963 0.711573 0.684891 0.301 Uiso calc 0.5 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 O1 . 2.0668(18) ?
Ni1 O1 2_656 2.0668(18) ?
Ni1 N2 . 2.075(2) ?
Ni1 N2 2_656 2.075(2) ?
Ni1 N3 . 2.077(2) ?
Ni1 N3 2_656 2.077(2) ?
Cl1 O3 . 1.045(9) ?
Cl1 O4 . 1.162(8) ?
Cl1 C3 . 1.738(6) ?
O1 C1 . 1.256(3) ?
O2 C2 . 1.236(4) ?
O3 N1 . 1.236(13) ?
O4 N1 . 1.181(13) ?
N1 C3 . 1.457(13) ?
N2 C4 . 1.333(3) ?
N2 C8 . 1.344(3) ?
N3 C9 . 1.335(3) ?
N3 C13 . 1.341(4) ?
C1 C3 . 1.387(4) ?
C1 C1 2_656 1.539(5) ?
C2 C3 . 1.409(4) ?
C2 C2 2_656 1.546(7) ?
C4 C5 . 1.380(4) ?
C4 H4 . 0.93 ?
C5 C6 . 1.379(5) ?
C5 H5 . 0.93 ?
C6 C7 . 1.372(5) ?
C6 H6 . 0.93 ?
C7 C8 . 1.387(4) ?
C7 H7 . 0.93 ?
C8 C9 . 1.482(4) ?
C9 C10 . 1.393(4) ?
C10 C11 . 1.376(5) ?
C10 H10 . 0.93 ?
C11 C12 . 1.376(6) ?
C11 H11 . 0.93 ?
C12 C13 . 1.389(5) ?
C12 H12 . 0.93 ?
C13 H13 . 0.93 ?
O5 C14 . 1.391(9) ?
O5 C14 2_556 1.90(2) ?
O5 H5O . 0.82 ?
C14 C15 . 1.454(9) ?
C14 H14A . 0.97 ?
C14 H14B . 0.97 ?
C14 H15C 2_556 1.083(14) ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
C15 H15A 2_556 0.96 ?
C15 H15B 2_556 0.9599 ?
C15 H15C 2_556 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
O1 Ni1 O1 78.74(10) . 2_656 ?
O1 Ni1 N2 169.78(7) . . ?
O1 Ni1 N2 94.44(7) 2_656 . ?
O1 Ni1 N2 94.44(8) . 2_656 ?
O1 Ni1 N2 169.78(7) 2_656 2_656 ?
N2 Ni1 N2 93.28(11) . 2_656 ?
O1 Ni1 N3 93.68(8) . . ?
O1 Ni1 N3 91.77(8) 2_656 . ?
N2 Ni1 N3 78.80(8) . . ?
N2 Ni1 N3 96.30(8) 2_656 . ?
O1 Ni1 N3 91.77(8) . 2_656 ?
O1 Ni1 N3 93.68(8) 2_656 2_656 ?
N2 Ni1 N3 96.30(8) . 2_656 ?
N2 Ni1 N3 78.80(8) 2_656 2_656 ?
N3 Ni1 N3 172.94(12) . 2_656 ?
O3 Cl1 O4 146.2(8) . . ?
O3 Cl1 C3 106.8(5) . . ?
O4 Cl1 C3 105.0(5) . . ?
C1 O1 Ni1 115.09(16) . . ?
Cl1 O3 N1 11.9(8) . . ?
Cl1 O4 N1 14.8(9) . . ?
O4 N1 O3 121.8(13) . . ?
O4 N1 C3 123.3(10) . . ?
O3 N1 C3 114.8(10) . . ?
C4 N2 C8 118.6(2) . . ?
C4 N2 Ni1 126.44(17) . . ?
C8 N2 Ni1 114.96(17) . . ?
C9 N3 C13 119.4(2) . . ?
C9 N3 Ni1 115.20(17) . . ?
C13 N3 Ni1 125.4(2) . . ?
O1 C1 C3 126.1(2) . . ?
O1 C1 C1 115.54(14) . 2_656 ?
C3 C1 C1 118.37(17) . 2_656 ?
O2 C2 C3 124.3(3) . . ?
O2 C2 C2 118.0(2) . 2_656 ?
C3 C2 C2 117.69(18) . 2_656 ?
C1 C3 C2 123.9(3) . . ?
C1 C3 N1 119.1(6) . . ?
C2 C3 N1 117.1(6) . . ?
C1 C3 Cl1 118.9(3) . . ?
C2 C3 Cl1 117.1(3) . . ?
N1 C3 Cl1 4.1(8) . . ?
N2 C4 C5 122.9(2) . . ?
N2 C4 H4 118.5 . . ?
C5 C4 H4 118.5 . . ?
C6 C5 C4 118.6(3) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C7 C6 C5 118.9(3) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C8 119.7(2) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
N2 C8 C7 121.3(2) . . ?
N2 C8 C9 115.5(2) . . ?
C7 C8 C9 123.2(2) . . ?
N3 C9 C10 121.5(3) . . ?
N3 C9 C8 115.5(2) . . ?
C10 C9 C8 123.0(3) . . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 119.0(3) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 119.2(3) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
N3 C13 C12 121.7(3) . . ?
N3 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C14 O5 C14 50.8(12) . 2_556 ?
C14 O5 H5O 109.5 . . ?
C14 O5 H5O 102.5 2_556 . ?
O5 C14 C15 114.4(12) . . ?
O5 C14 O5 100.3(13) . 2_556 ?
C15 C14 O5 89.9(9) . 2_556 ?
O5 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
O5 C14 H14A 134 2_556 . ?
O5 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
O5 C14 H14B 27.4 2_556 . ?
H14A C14 H14B 107.6 . . ?
O5 C14 H15C 128.4(15) . 2_556 ?
C15 C14 H15C 41.3(3) . 2_556 ?
O5 C14 H15C 119.0(11) 2_556 2_556 ?
H14A C14 H15C 67.4 . 2_556 ?
H14B C14 H15C 121.8 . 2_556 ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C15 H15A 121.2(6) . 2_556 ?
H15A C15 H15A 120.7 . 2_556 ?
H15B C15 H15A 27.6 . 2_556 ?
H15C C15 H15A 81.9 . 2_556 ?
C14 C15 H15B 128.8(6) . 2_556 ?
H15A C15 H15B 27.6 . 2_556 ?
H15B C15 H15B 112.1 . 2_556 ?
H15C C15 H15B 83.3 . 2_556 ?
H15A C15 H15B 109.5 2_556 2_556 ?
C14 C15 H15C 48.2(7) . 2_556 ?
H15A C15 H15C 81.9 . 2_556 ?
H15B C15 H15C 83.3 . 2_556 ?
H15C C15 H15C 157.6 . 2_556 ?
H15A C15 H15C 109.5 2_556 2_556 ?
H15B C15 H15C 109.5 2_556 2_556 ?

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
O4 Cl1 O3 N1 -146(6) . . . . ?
C3 Cl1 O3 N1 14(5) . . . . ?
O3 Cl1 O4 N1 152(5) . . . . ?
C3 Cl1 O4 N1 -8(4) . . . . ?
Cl1 O4 N1 O3 -15(3) . . . . ?
Cl1 O4 N1 C3 169(5) . . . . ?
Cl1 O3 N1 O4 21(4) . . . . ?
Cl1 O3 N1 C3 -163(6) . . . . ?
Ni1 O1 C1 C3 -179.2(2) . . . . ?
Ni1 O1 C1 C1 0.5(3) . . . 2_656 ?
O1 C1 C3 C2 -178.1(2) . . . . ?
C1 C1 C3 C2 2.2(4) 2_656 . . . ?
O1 C1 C3 N1 2.1(8) . . . . ?
C1 C1 C3 N1 -177.5(7) 2_656 . . . ?
O1 C1 C3 Cl1 -2.6(4) . . . . ?
C1 C1 C3 Cl1 177.7(3) 2_656 . . . ?
O2 C2 C3 C1 175.5(3) . . . . ?
C2 C2 C3 C1 -3.7(4) 2_656 . . . ?
O2 C2 C3 N1 -4.7(8) . . . . ?
C2 C2 C3 N1 176.1(7) 2_656 . . . ?
O2 C2 C3 Cl1 -0.1(4) . . . . ?
C2 C2 C3 Cl1 -179.3(3) 2_656 . . . ?
O4 N1 C3 C1 117.5(12) . . . . ?
O3 N1 C3 C1 -58.5(16) . . . . ?
O4 N1 C3 C2 -62.3(17) . . . . ?
O3 N1 C3 C2 121.7(11) . . . . ?
O4 N1 C3 Cl1 -153(11) . . . . ?
O3 N1 C3 Cl1 31(9) . . . . ?
O3 Cl1 C3 C1 -52.0(8) . . . . ?
O4 Cl1 C3 C1 116.3(6) . . . . ?
O3 Cl1 C3 C2 123.8(7) . . . . ?
O4 Cl1 C3 C2 -67.8(6) . . . . ?
O3 Cl1 C3 N1 -145(10) . . . . ?
O4 Cl1 C3 N1 23(10) . . . . ?
C8 N2 C4 C5 -0.3(4) . . . . ?
Ni1 N2 C4 C5 178.4(2) . . . . ?
N2 C4 C5 C6 1.0(5) . . . . ?
C4 C5 C6 C7 -0.7(5) . . . . ?
C5 C6 C7 C8 -0.2(5) . . . . ?
C4 N2 C8 C7 -0.7(4) . . . . ?
Ni1 N2 C8 C7 -179.48(19) . . . . ?
C4 N2 C8 C9 180.0(2) . . . . ?
Ni1 N2 C8 C9 1.2(3) . . . . ?
C6 C7 C8 N2 0.9(4) . . . . ?
C6 C7 C8 C9 -179.8(3) . . . . ?
C13 N3 C9 C10 -0.4(4) . . . . ?
Ni1 N3 C9 C10 179.1(2) . . . . ?
C13 N3 C9 C8 179.4(2) . . . . ?
Ni1 N3 C9 C8 -1.1(3) . . . . ?
N2 C8 C9 N3 0.0(3) . . . . ?
C7 C8 C9 N3 -179.4(2) . . . . ?
N2 C8 C9 C10 179.7(2) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
N3 C9 C10 C11 0.7(4) . . . . ?
C8 C9 C10 C11 -179.1(3) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
C10 C11 C12 C13 -0.8(5) . . . . ?
C9 N3 C13 C12 -0.5(4) . . . . ?
Ni1 N3 C13 C12 -179.9(2) . . . . ?
C11 C12 C13 N3 1.1(5) . . . . ?
C14 O5 C14 C15 -51.4(11) 2_556 . . . ?
C14 O5 C14 O5 43.2(6) 2_556 . . 2_556 ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_v_s94b
_database_code_depnum_ccdc_archive 'CCDC 2048078'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2020-12-03 deposited with the CCDC.	2021-02-25 downloaded from the CCDC.
;

_audit_creation_date             2019-10-21T11:15:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum            'C22 H16 Cl2 Mn N4 O14'
_chemical_formula_moiety         'C12 H4 Cl2 Mn N2 O14, 2(C5 H6 N)'
_chemical_formula_weight         686.23

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   8.159(3)
_cell_length_b                   9.129(3)
_cell_length_c                   9.870(6)
_cell_angle_alpha                72.10(4)
_cell_angle_beta                 70.60(4)
_cell_angle_gamma                67.07(3)
_cell_volume                     625.0(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      7.53
_cell_measurement_theta_max      15.72
_cell_measurement_temperature    293(2)
_exptl_crystal_description       rod
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_F_000             347
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_type   none

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled ω/2τ scans'
_diffrn_reflns_number            2659
_diffrn_reflns_av_R_equivalents  0.1175
_diffrn_reflns_theta_min         2.235
_diffrn_reflns_theta_max         24.947
_diffrn_reflns_theta_full        24.947
_diffrn_measured_fraction_theta_max 1
_diffrn_measured_fraction_theta_full 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       0
_diffrn_standards_number         3
_diffrn_standards_interval_time  500
_diffrn_standards_decay_%        1
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 1 -1
2 2 0
-1 2 -2


#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   mixed

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             2195
_reflns_number_gt                1450
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1337
_refine_ls_R_factor_gt           0.0741
_refine_ls_wR_factor_ref         0.1986
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.081
_refine_ls_number_reflns         2195
_refine_ls_number_parameters     230
_refine_ls_number_restraints     5
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0934P)²+1.4985P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.812
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.13
_refine_ls_extinction_method     none
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'
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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 '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'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Mn1 0 1 0.5 0.0291(5) Uani d 1 . . Mn
O1 0.4812(6) 0.2492(5) 0.7039(6) 0.0390(12) Uani d 1 . . O
O2 0.4100(7) 0.2284(5) 0.4729(6) 0.0438(13) Uani d 1 . . O
O3 0.0782(6) 0.7891(5) 0.4030(5) 0.0325(11) Uani d 1 . . O
O4 0.1083(6) 0.7927(5) 0.6586(5) 0.0329(11) Uani d 1 . . O
Cl1A 0.2982(9) 0.5228(9) 0.8680(5) 0.0515(16) Uani d 0.712(11) A 1 Cl
O5A 0.2049(11) 0.3681(9) 0.2805(9) 0.053(3) Uani d 0.712(11) A 1 O
O6A 0.1851(15) 0.6172(10) 0.1962(10) 0.074(3) Uani d 0.712(11) A 1 O
N1A 0.204(9) 0.498(8) 0.288(4) 0.047(2) Uani d 0.712(11) A 1 N
Cl1B 0.200(6) 0.501(6) 0.267(3) 0.047(2) Uani d 0.288(11) A 2 Cl
N1B 0.323(10) 0.513(9) 0.837(5) 0.0515(16) Uani d 0.288(11) A 2 N
O5B 0.147(4) 0.557(4) 0.932(2) 0.101(11) Uani d 0.288(11) A 2 O
O6B 0.438(4) 0.477(4) 0.864(3) 0.120(13) Uani d 0.288(11) A 2 O
C1 0.3729(8) 0.3725(7) 0.6455(7) 0.0284(14) Uani d 1 . . C
C2 0.3392(9) 0.3619(7) 0.5065(7) 0.0296(15) Uani d 1 . . C
C3 0.2324(8) 0.5057(7) 0.4266(7) 0.0293(14) Uani d 1 . . C
C4 0.1633(8) 0.6550(7) 0.4722(7) 0.0250(13) Uani d 1 . . C
C5 0.1828(8) 0.6580(7) 0.6180(7) 0.0269(14) Uani d 1 . . C
C6 0.2811(9) 0.5179(7) 0.6995(7) 0.0291(15) Uani d 1 . . C
O7 0.2731(6) 1.0243(6) 0.4048(6) 0.0402(13) Uani d 1 . . O
H7A 0.351(12) 0.947(11) 0.432(10) 0.06 Uiso d 1 . . H
H7B 0.301(11) 1.110(10) 0.412(9) 0.06 Uiso d 1 . . H
N2 0.6512(11) 0.1042(9) 0.9439(9) 0.061(2) Uani d 1 . . N
C7 0.6124(12) 0.1596(10) 1.0621(11) 0.056(2) Uani d 1 . . C
H7 0.525751 0.261169 1.070709 0.067 Uiso calc 1 . . H
C8 0.6960(13) 0.0718(12) 1.1711(10) 0.061(2) Uani d 1 . . C
H8 0.667147 0.110311 1.255844 0.073 Uiso calc 1 . . H
C9 0.8273(12) -0.0788(11) 1.1539(10) 0.058(2) Uani d 1 . . C
H9 0.89135 -0.140624 1.225787 0.07 Uiso calc 1 . . H
C10 0.8614(12) -0.1348(10) 1.0306(11) 0.061(2) Uani d 1 . . C
H10 0.944605 -0.237257 1.019905 0.073 Uiso calc 1 . . H
C11 0.7711(14) -0.0381(13) 0.9223(10) 0.066(3) Uani d 1 . . C
H11 0.794223 -0.072536 0.836317 0.08 Uiso calc 1 . . H
H2 0.591(12) 0.170(9) 0.880(8) 0.08 Uiso d 1 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Mn1 O4 . 2.146(4) ?
Mn1 O4 2_576 2.146(4) ?
Mn1 O7 2_576 2.182(5) ?
Mn1 O7 . 2.182(5) ?
Mn1 O3 2_576 2.190(4) ?
Mn1 O3 . 2.190(4) ?
O1 C1 . 1.243(7) ?
O2 C2 . 1.226(7) ?
O3 C4 . 1.259(7) ?
O4 C5 . 1.265(7) ?
Cl1A C6 . 1.730(7) ?
O5A N1A . 1.20(6) ?
O6A N1A . 1.18(6) ?
N1A C3 . 1.487(17) ?
Cl1B C3 . 1.697(14) ?
N1B O6B . 0.97(6) ?
N1B O5B . 1.41(7) ?
N1B C6 . 1.49(2) ?
C1 C6 . 1.415(8) ?
C1 C2 . 1.523(9) ?
C2 C3 . 1.426(8) ?
C3 C4 . 1.410(8) ?
C4 C5 . 1.509(9) ?
C5 C6 . 1.387(8) ?
O7 H7A . 0.79(9) ?
O7 H7B . 0.92(9) ?
N2 C7 . 1.308(12) ?
N2 C11 . 1.316(12) ?
N2 H2 . 0.86(2) ?
C7 C8 . 1.340(12) ?
C7 H7 . 0.93 ?
C8 C9 . 1.393(13) ?
C8 H8 . 0.93 ?
C9 C10 . 1.366(13) ?
C9 H9 . 0.93 ?
C10 C11 . 1.379(13) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?

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
O4 Mn1 O4 180.0(2) . 2_576 ?
O4 Mn1 O7 90.57(19) . 2_576 ?
O4 Mn1 O7 89.43(19) 2_576 2_576 ?
O4 Mn1 O7 89.43(19) . . ?
O4 Mn1 O7 90.57(19) 2_576 . ?
O7 Mn1 O7 180 2_576 . ?
O4 Mn1 O3 105.52(16) . 2_576 ?
O4 Mn1 O3 74.48(16) 2_576 2_576 ?
O7 Mn1 O3 91.67(18) 2_576 2_576 ?
O7 Mn1 O3 88.33(18) . 2_576 ?
O4 Mn1 O3 74.48(16) . . ?
O4 Mn1 O3 105.52(16) 2_576 . ?
O7 Mn1 O3 88.33(18) 2_576 . ?
O7 Mn1 O3 91.67(18) . . ?
O3 Mn1 O3 180 2_576 . ?
C4 O3 Mn1 115.8(4) . . ?
C5 O4 Mn1 116.4(4) . . ?
O6A N1A O5A 126.3(16) . . ?
O6A N1A C3 117(4) . . ?
O5A N1A C3 116(4) . . ?
O6B N1B O5B 125(4) . . ?
O6B N1B C6 132(6) . . ?
O5B N1B C6 103(4) . . ?
O1 C1 C6 124.6(6) . . ?
O1 C1 C2 116.2(5) . . ?
C6 C1 C2 119.2(5) . . ?
O2 C2 C3 126.0(6) . . ?
O2 C2 C1 115.8(6) . . ?
C3 C2 C1 118.2(5) . . ?
C4 C3 C2 121.3(6) . . ?
C4 C3 N1A 120(2) . . ?
C2 C3 N1A 119(2) . . ?
C4 C3 Cl1B 118.9(16) . . ?
C2 C3 Cl1B 119.7(16) . . ?
O3 C4 C3 125.2(6) . . ?
O3 C4 C5 115.7(5) . . ?
C3 C4 C5 119.1(5) . . ?
O4 C5 C6 123.2(6) . . ?
O4 C5 C4 116.8(5) . . ?
C6 C5 C4 120.0(5) . . ?
C5 C6 C1 121.4(6) . . ?
C5 C6 N1B 124(3) . . ?
C1 C6 N1B 114(3) . . ?
C5 C6 Cl1A 119.3(5) . . ?
C1 C6 Cl1A 119.3(5) . . ?
Mn1 O7 H7A 113(6) . . ?
Mn1 O7 H7B 122(5) . . ?
H7A O7 H7B 104(8) . . ?
C7 N2 C11 123.9(8) . . ?
C7 N2 H2 114(7) . . ?
C11 N2 H2 122(7) . . ?
N2 C7 C8 120.8(8) . . ?
N2 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C9 118.2(9) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?
C10 C9 C8 119.5(8) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 119.4(8) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
N2 C11 C10 118.1(9) . . ?
N2 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O2 5.9(9) . . . . ?
C6 C1 C2 O2 -173.8(6) . . . . ?
O1 C1 C2 C3 -173.1(6) . . . . ?
C6 C1 C2 C3 7.1(9) . . . . ?
O2 C2 C3 C4 -177.4(6) . . . . ?
C1 C2 C3 C4 1.6(9) . . . . ?
O2 C2 C3 N1A -1(3) . . . . ?
C1 C2 C3 N1A 178(3) . . . . ?
O2 C2 C3 Cl1B -2(2) . . . . ?
C1 C2 C3 Cl1B 177(2) . . . . ?
O6A N1A C3 C4 27(6) . . . . ?
O5A N1A C3 C4 -155(3) . . . . ?
O6A N1A C3 C2 -150(4) . . . . ?
O5A N1A C3 C2 29(6) . . . . ?
Mn1 O3 C4 C3 -177.4(5) . . . . ?
Mn1 O3 C4 C5 5.4(7) . . . . ?
C2 C3 C4 O3 175.2(6) . . . . ?
N1A C3 C4 O3 -1(3) . . . . ?
Cl1B C3 C4 O3 0(2) . . . . ?
C2 C3 C4 C5 -7.7(9) . . . . ?
N1A C3 C4 C5 176(3) . . . . ?
Cl1B C3 C4 C5 177(2) . . . . ?
Mn1 O4 C5 C6 170.7(5) . . . . ?
Mn1 O4 C5 C4 -8.3(7) . . . . ?
O3 C4 C5 O4 1.8(8) . . . . ?
C3 C4 C5 O4 -175.5(6) . . . . ?
O3 C4 C5 C6 -177.2(6) . . . . ?
C3 C4 C5 C6 5.5(9) . . . . ?
O4 C5 C6 C1 -175.6(6) . . . . ?
C4 C5 C6 C1 3.4(9) . . . . ?
O4 C5 C6 N1B -5(4) . . . . ?
C4 C5 C6 N1B 174(4) . . . . ?
O4 C5 C6 Cl1A 2.2(10) . . . . ?
C4 C5 C6 Cl1A -178.8(5) . . . . ?
O1 C1 C6 C5 170.7(6) . . . . ?
C2 C1 C6 C5 -9.5(9) . . . . ?
O1 C1 C6 N1B -1(4) . . . . ?
C2 C1 C6 N1B 179(4) . . . . ?
O1 C1 C6 Cl1A -7.1(10) . . . . ?
C2 C1 C6 Cl1A 172.6(5) . . . . ?
O6B N1B C6 C5 -124(9) . . . . ?
O5B N1B C6 C5 64(6) . . . . ?
O6B N1B C6 C1 47(11) . . . . ?
O5B N1B C6 C1 -125(3) . . . . ?
C11 N2 C7 C8 0.3(14) . . . . ?
N2 C7 C8 C9 1.0(13) . . . . ?
C7 C8 C9 C10 -2.6(13) . . . . ?
C8 C9 C10 C11 2.9(13) . . . . ?
C7 N2 C11 C10 0.0(13) . . . . ?
C9 C10 C11 N2 -1.6(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
_geom_hbond_publ_flag
O7 H7A O1 0.79(9) 2.29(9) 2.779(6) 121(8) 2_666 yes
O7 H7A O2 0.79(9) 2.26(9) 3.030(7) 166(8) 2_666 yes
O7 H7B O2 0.92(9) 1.96(9) 2.838(7) 160(7) 1_565 yes
O7 H7B O5A^a 0.92(9) 2.29(8) 2.896(9) 124(7) 1_565 yes
N2 H2 O1 0.86(2) 2.03(4) 2.848(9) 159(9) . yes
N2 H2 Cl1A^a 0.86(2) 3.17(7) 3.816(10) 133(8) . yes
N2 H2 O6B^b 0.86(2) 2.56(9) 3.14(3) 125(8) . yes
C7 H7 O6B^b 0.93 2.44 3.06(3) 124.6 . yes
C8 H8 O2 0.93 2.61 3.430(10) 147 1_556 yes
C10 H10 O5B^b 0.93 2.15 3.06(3) 164.2 1_645 yes
C11 H11 O4 0.93 2.65 3.336(11) 130.8 1_645 yes
C11 H11 O7 0.93 2.49 3.325(11) 149.6 2_666 yes



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_s268_100k
_database_code_depnum_ccdc_archive 'CCDC 2048079'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2020-12-03 deposited with the CCDC.	2021-02-25 downloaded from the CCDC.
;

_audit_creation_date             2019-10-21T14:56:03-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum            'C16 H8 Cl Cu N3 O6'
_chemical_formula_moiety         'C16 H8 Cl Cu N3 O6'
_chemical_formula_weight         437.24

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   7.9877(5)
_cell_length_b                   8.4472(5)
_cell_length_c                   12.6121(7)
_cell_angle_alpha                107.683(5)
_cell_angle_beta                 105.070(5)
_cell_angle_gamma                93.519(5)
_cell_volume                     773.73(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3641
_cell_measurement_theta_min      5.558
_cell_measurement_theta_max      75.936
_cell_measurement_temperature    293(2)
_exptl_crystal_description       plate
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.877
_exptl_crystal_F_000             438
_exptl_absorpt_coefficient_mu    4.006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.83425
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            6466
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_theta_min         5.562
_diffrn_reflns_theta_max         76.409
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             3190
_reflns_number_gt                2928
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0991
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_restrained_S_all      1.062
_refine_ls_number_reflns         3190
_refine_ls_number_parameters     263
_refine_ls_number_restraints     15
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0526P)²+0.6209P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.742
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
Cu Cu -1.9646 0.5888 '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'

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cu1 0.36334(4) 0.56598(4) 0.08807(3) 0.01686(12) Uani d 1 . . Cu
Cl1A 0.30708(11) -0.03461(8) -0.11982(7) 0.0229(2) Uani d 0.920(3) A 1 Cl
O5A -0.1678(3) 0.4856(3) -0.34782(17) 0.0307(5) Uani d 0.920(3) A 1 O
O6A -0.1598(2) 0.5804(2) -0.16597(16) 0.0232(4) Uani d 0.920(3) A 1 O
N1A -0.1186(4) 0.4840(5) -0.2491(3) 0.0235(7) Uani d 0.920(3) A 1 N
Cl1B -0.1330(16) 0.5304(15) -0.2464(12) 0.0235(7) Uani d 0.080(3) A 2 Cl
O5B 0.406(3) 0.004(3) -0.094(2) 0.025(4) Uani d 0.080(3) A 2 O
O6B 0.144(3) -0.141(2) -0.152(2) 0.025(4) Uani d 0.080(3) A 2 O
N1B 0.252(3) -0.029(3) -0.131(3) 0.0229(2) Uani d 0.080(3) A 2 N
O1 0.1738(2) 0.55606(19) -0.04702(13) 0.0192(3) Uani d 1 . . O
O2 0.3694(2) 0.3367(2) -0.00212(14) 0.0208(3) Uani d 1 . . O
O3 0.0236(2) -0.0829(2) -0.34175(15) 0.0282(4) Uani d 1 . . O
O4 -0.1767(2) 0.1447(2) -0.39475(15) 0.0264(4) Uani d 1 . . O
N2 0.3708(2) 0.8028(2) 0.17784(16) 0.0168(4) Uani d 1 . . N
N3 0.5439(2) 0.5743(2) 0.22973(16) 0.0158(4) Uani d 1 . . N
C1 0.1252(3) 0.4084(3) -0.12120(19) 0.0162(4) Uani d 1 . . C
C2 0.2344(3) 0.2783(3) -0.09291(19) 0.0172(4) Uani d 1 . . C
C3 0.1879(3) 0.1132(3) -0.16149(19) 0.0187(4) Uani d 1 . . C
C4 0.0548(3) 0.0598(3) -0.2725(2) 0.0206(5) Uani d 1 . . C
C5 -0.0553(3) 0.1938(3) -0.30479(19) 0.0200(5) Uani d 1 . . C
C6 -0.0113(3) 0.3623(3) -0.2236(2) 0.0185(4) Uani d 1 . . C
C7 0.2709(3) 0.9083(3) 0.1405(2) 0.0196(4) Uani d 1 . . C
H7 0.188741 0.868689 0.06733 0.024 Uiso calc 1 . . H
C8 0.2874(3) 1.0748(3) 0.2085(2) 0.0216(5) Uani d 1 . . C
H8 0.216585 1.146283 0.181766 0.026 Uiso calc 1 . . H
C9 0.4108(3) 1.1329(3) 0.3165(2) 0.0214(5) Uani d 1 . . C
H9 0.423621 1.244377 0.363329 0.026 Uiso calc 1 . . H
C10 0.5160(3) 1.0245(3) 0.3554(2) 0.0199(4) Uani d 1 . . C
H10 0.600237 1.062275 0.42775 0.024 Uiso calc 1 . . H
C11 0.4921(3) 0.8583(3) 0.28335(18) 0.0160(4) Uani d 1 . . C
C12 0.5907(3) 0.7272(3) 0.31385(19) 0.0167(4) Uani d 1 . . C
C13 0.7186(3) 0.7528(3) 0.41819(19) 0.0198(4) Uani d 1 . . C
H13 0.751393 0.858522 0.475016 0.024 Uiso calc 1 . . H
C14 0.7970(3) 0.6161(3) 0.4359(2) 0.0219(5) Uani d 1 . . C
H14 0.883213 0.630132 0.505148 0.026 Uiso calc 1 . . H
C15 0.7459(3) 0.4592(3) 0.3501(2) 0.0219(5) Uani d 1 . . C
H15 0.795552 0.366649 0.36141 0.026 Uiso calc 1 . . H
C16 0.6196(3) 0.4434(3) 0.2474(2) 0.0189(4) Uani d 1 . . C
H16 0.586281 0.339127 0.188939 0.023 Uiso calc 1 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O2 . 1.9364(16) ?
Cu1 O1 . 1.9386(16) ?
Cu1 N3 . 1.9619(19) ?
Cu1 N2 . 1.9649(19) ?
Cl1A C3 . 1.739(2) ?
O5A N1A . 1.209(4) ?
O6A N1A . 1.251(4) ?
N1A C6 . 1.435(4) ?
Cl1B C6 . 1.821(12) ?
O5B N1B . 1.172(18) ?
O6B N1B . 1.162(18) ?
N1B C3 . 1.453(18) ?
O1 C1 . 1.274(3) ?
O2 C2 . 1.291(3) ?
O3 C4 . 1.220(3) ?
O4 C5 . 1.221(3) ?
N2 C7 . 1.342(3) ?
N2 C11 . 1.350(3) ?
N3 C16 . 1.342(3) ?
N3 C12 . 1.355(3) ?
C1 C6 . 1.385(3) ?
C1 C2 . 1.514(3) ?
C2 C3 . 1.367(3) ?
C3 C4 . 1.442(3) ?
C4 C5 . 1.561(3) ?
C5 C6 . 1.437(3) ?
C7 C8 . 1.384(3) ?
C7 H7 . 0.93 ?
C8 C9 . 1.380(3) ?
C8 H8 . 0.93 ?
C9 C10 . 1.392(3) ?
C9 H9 . 0.93 ?
C10 C11 . 1.391(3) ?
C10 H10 . 0.93 ?
C11 C12 . 1.484(3) ?
C12 C13 . 1.387(3) ?
C13 C14 . 1.395(3) ?
C13 H13 . 0.93 ?
C14 C15 . 1.389(3) ?
C14 H14 . 0.93 ?
C15 C16 . 1.383(3) ?
C15 H15 . 0.93 ?
C16 H16 . 0.93 ?

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
O2 Cu1 O1 84.04(7) . . ?
O2 Cu1 N3 96.77(7) . . ?
O1 Cu1 N3 176.37(7) . . ?
O2 Cu1 N2 176.46(7) . . ?
O1 Cu1 N2 97.01(7) . . ?
N3 Cu1 N2 82.39(8) . . ?
O5A N1A O6A 123.8(3) . . ?
O5A N1A C6 119.6(3) . . ?
O6A N1A C6 116.6(3) . . ?
O6B N1B O5B 139(2) . . ?
O6B N1B C3 114.1(19) . . ?
O5B N1B C3 107.3(17) . . ?
C1 O1 Cu1 112.85(14) . . ?
C2 O2 Cu1 111.86(14) . . ?
C7 N2 C11 120.16(19) . . ?
C7 N2 Cu1 125.17(16) . . ?
C11 N2 Cu1 114.64(15) . . ?
C16 N3 C12 119.97(19) . . ?
C16 N3 Cu1 125.25(15) . . ?
C12 N3 Cu1 114.78(15) . . ?
O1 C1 C6 125.7(2) . . ?
O1 C1 C2 114.82(19) . . ?
C6 C1 C2 119.48(19) . . ?
O2 C2 C3 124.8(2) . . ?
O2 C2 C1 114.89(19) . . ?
C3 C2 C1 120.3(2) . . ?
C2 C3 C4 122.1(2) . . ?
C2 C3 N1B 126.1(14) . . ?
C4 C3 N1B 111.7(13) . . ?
C2 C3 Cl1A 118.81(18) . . ?
C4 C3 Cl1A 118.81(17) . . ?
O3 C4 C3 123.9(2) . . ?
O3 C4 C5 118.6(2) . . ?
C3 C4 C5 117.47(19) . . ?
O4 C5 C6 125.4(2) . . ?
O4 C5 C4 117.0(2) . . ?
C6 C5 C4 117.4(2) . . ?
C1 C6 N1A 119.7(2) . . ?
C1 C6 C5 122.5(2) . . ?
N1A C6 C5 117.8(2) . . ?
C1 C6 Cl1B 115.0(5) . . ?
C5 C6 Cl1B 122.5(5) . . ?
N2 C7 C8 121.5(2) . . ?
N2 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 118.9(2) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 120.0(2) . . ?
C8 C9 H9 120 . . ?
C10 C9 H9 120 . . ?
C11 C10 C9 118.4(2) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
N2 C11 C10 121.1(2) . . ?
N2 C11 C12 114.24(19) . . ?
C10 C11 C12 124.6(2) . . ?
N3 C12 C13 121.3(2) . . ?
N3 C12 C11 113.86(19) . . ?
C13 C12 C11 124.9(2) . . ?
C12 C13 C14 118.5(2) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 118.6(2) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
N3 C16 C15 121.8(2) . . ?
N3 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 C6 177.40(18) . . . . ?
Cu1 O1 C1 C2 -4.9(2) . . . . ?
Cu1 O2 C2 C3 -168.39(18) . . . . ?
Cu1 O2 C2 C1 11.8(2) . . . . ?
O1 C1 C2 O2 -4.8(3) . . . . ?
C6 C1 C2 O2 173.09(19) . . . . ?
O1 C1 C2 C3 175.4(2) . . . . ?
C6 C1 C2 C3 -6.7(3) . . . . ?
O2 C2 C3 C4 -168.9(2) . . . . ?
C1 C2 C3 C4 10.9(3) . . . . ?
O2 C2 C3 N1B 15.9(16) . . . . ?
C1 C2 C3 N1B -164.3(16) . . . . ?
O2 C2 C3 Cl1A 5.0(3) . . . . ?
C1 C2 C3 Cl1A -175.17(15) . . . . ?
O6B N1B C3 C2 134(3) . . . . ?
O5B N1B C3 C2 -48(4) . . . . ?
O6B N1B C3 C4 -42(4) . . . . ?
O5B N1B C3 C4 136(3) . . . . ?
C2 C3 C4 O3 171.4(2) . . . . ?
N1B C3 C4 O3 -12.8(15) . . . . ?
Cl1A C3 C4 O3 -2.5(3) . . . . ?
C2 C3 C4 C5 -8.7(3) . . . . ?
N1B C3 C4 C5 167.1(14) . . . . ?
Cl1A C3 C4 C5 177.37(15) . . . . ?
O3 C4 C5 O4 5.4(3) . . . . ?
C3 C4 C5 O4 -174.5(2) . . . . ?
O3 C4 C5 C6 -177.7(2) . . . . ?
C3 C4 C5 C6 2.4(3) . . . . ?
O1 C1 C6 N1A -4.3(3) . . . . ?
C2 C1 C6 N1A 178.12(19) . . . . ?
O1 C1 C6 C5 178.2(2) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
O1 C1 C6 Cl1B -2.8(4) . . . . ?
C2 C1 C6 Cl1B 179.6(2) . . . . ?
O5A N1A C6 C1 141.3(3) . . . . ?
O6A N1A C6 C1 -40.8(4) . . . . ?
O5A N1A C6 C5 -41.0(4) . . . . ?
O6A N1A C6 C5 136.9(3) . . . . ?
O4 C5 C6 C1 178.0(2) . . . . ?
C4 C5 C6 C1 1.3(3) . . . . ?
O4 C5 C6 N1A 0.4(3) . . . . ?
C4 C5 C6 N1A -176.26(19) . . . . ?
O4 C5 C6 Cl1B -1.0(4) . . . . ?
C4 C5 C6 Cl1B -177.6(3) . . . . ?
C11 N2 C7 C8 -0.6(3) . . . . ?
Cu1 N2 C7 C8 -178.48(16) . . . . ?
N2 C7 C8 C9 0.6(3) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C7 N2 C11 C10 0.1(3) . . . . ?
Cu1 N2 C11 C10 178.17(16) . . . . ?
C7 N2 C11 C12 179.07(19) . . . . ?
Cu1 N2 C11 C12 -2.9(2) . . . . ?
C9 C10 C11 N2 0.5(3) . . . . ?
C9 C10 C11 C12 -178.4(2) . . . . ?
C16 N3 C12 C13 1.1(3) . . . . ?
Cu1 N3 C12 C13 -179.09(16) . . . . ?
C16 N3 C12 C11 -178.20(18) . . . . ?
Cu1 N3 C12 C11 1.6(2) . . . . ?
N2 C11 C12 N3 0.8(3) . . . . ?
C10 C11 C12 N3 179.8(2) . . . . ?
N2 C11 C12 C13 -178.4(2) . . . . ?
C10 C11 C12 C13 0.5(3) . . . . ?
N3 C12 C13 C14 -1.0(3) . . . . ?
C11 C12 C13 C14 178.2(2) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C16 1.2(4) . . . . ?
C12 N3 C16 C15 0.0(3) . . . . ?
Cu1 N3 C16 C15 -179.77(17) . . . . ?
C14 C15 C16 N3 -1.1(4) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_s328_120k
_database_code_depnum_ccdc_archive 'CCDC 2048074'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2020-12-03 deposited with the CCDC.	2021-02-25 downloaded from the CCDC.
;

_audit_creation_date             2019-10-22T09:52:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum            'C6 H6 Cl N Na2 O9'
_chemical_formula_moiety         'C6 H6 Cl N Na2 O9'
_chemical_formula_weight         317.55

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   6.6229(4)
_cell_length_b                   8.5080(4)
_cell_length_c                   9.8303(6)
_cell_angle_alpha                105.234(5)
_cell_angle_beta                 92.783(5)
_cell_angle_gamma                93.104(5)
_cell_volume                     532.53(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2684
_cell_measurement_theta_min      4.664
_cell_measurement_theta_max      75.606
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.98
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    4.496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.48199
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            4302
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_theta_min         4.672
_diffrn_reflns_theta_max         76.19
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   difmap

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             2201
_reflns_number_gt                2070
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.1031
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_number_reflns         2201
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0637P)²+0.2275P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
Ag Ag 0.1306 4.282 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Na1 0.32529(12) 0.11415(9) -0.03756(8) 0.0179(2) Uani d 1 . . Na
Na2 0.21446(12) -0.02558(9) 0.59755(8) 0.0178(2) Uani d 1 . . Na
Cl1 0.25886(6) 0.40553(5) 0.72886(4) 0.01727(15) Uani d 1 . . Cl
O1 0.1956(2) 0.14795(16) 0.45089(14) 0.0199(3) Uani d 1 . . O
O2 0.2231(2) 0.18666(16) 0.19665(14) 0.0166(3) Uani d 1 . . O
O3 0.2510(2) 0.76068(16) 0.39217(14) 0.0188(3) Uani d 1 . . O
O4 0.2644(2) 0.71643(16) 0.64397(14) 0.0187(3) Uani d 1 . . O
O5 0.2840(3) 0.39141(18) 0.03732(15) 0.0294(4) Uani d 1 . . O
O6 0.1961(2) 0.63490(17) 0.11981(15) 0.0237(3) Uani d 1 . . O
N1 0.2373(2) 0.49998(18) 0.13505(16) 0.0131(3) Uani d 1 . . N
C1 0.2211(3) 0.2914(2) 0.44388(19) 0.0142(4) Uani d 1 . . C
C2 0.2276(3) 0.3150(2) 0.29291(18) 0.0132(3) Uani d 1 . . C
C3 0.2354(3) 0.4765(2) 0.27575(18) 0.0140(4) Uani d 1 . . C
C4 0.2436(3) 0.6160(2) 0.39517(19) 0.0137(3) Uani d 1 . . C
C5 0.2533(3) 0.5902(2) 0.54517(19) 0.0135(3) Uani d 1 . . C
C6 0.2470(3) 0.4303(2) 0.55935(18) 0.0137(3) Uani d 1 . . C
O7 0.0434(2) 0.08306(18) -0.19629(15) 0.0183(3) Uani d 1 . . O
H7A -0.010(4) 0.148(4) -0.200(3) 0.022 Uiso d 1 . . H
H7B -0.048(4) 0.015(4) -0.201(3) 0.022 Uiso d 1 . . H
O8 0.3306(2) -0.17007(17) -0.06630(15) 0.0193(3) Uani d 1 . . O
H8A 0.308(4) -0.215(4) -0.143(3) 0.023 Uiso d 1 . . H
H8B 0.273(4) -0.243(3) -0.031(3) 0.023 Uiso d 1 . . H
O9 0.5077(2) 0.05843(17) 0.74871(15) 0.0173(3) Uani d 1 . . O
H9A 0.575(4) -0.005(4) 0.738(3) 0.021 Uiso d 1 . . H
H9B 0.577(4) 0.131(4) 0.730(3) 0.021 Uiso d 1 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Na1 O5 . 2.3148(16) ?
Na1 O7 . 2.3320(17) ?
Na1 O8 . 2.3621(16) ?
Na1 O2 . 2.3642(15) ?
Na1 O8 2_655 2.4217(17) ?
Na1 O9 1_554 2.4256(15) ?
Na1 Na1 2_655 3.2784(15) ?
Na1 Na2 1_554 3.4968(11) ?
Na2 O1 . 2.3227(14) ?
Na2 O9 . 2.3456(17) ?
Na2 O7 1_556 2.3660(16) ?
Na2 O3 1_545 2.3681(15) ?
Na2 O4 1_545 2.3928(15) ?
Na2 O1 2_556 2.8272(17) ?
Na2 Na2 2_556 3.4614(16) ?
Na2 H9A . 2.67(3) ?
Cl1 C6 . 1.7322(17) ?
O1 C1 . 1.244(2) ?
O2 C2 . 1.241(2) ?
O3 C4 . 1.237(2) ?
O4 C5 . 1.240(2) ?
O5 N1 . 1.211(2) ?
O6 N1 . 1.239(2) ?
N1 C3 . 1.449(2) ?
C1 C6 . 1.403(3) ?
C1 C2 . 1.551(2) ?
C2 C3 . 1.427(2) ?
C3 C4 . 1.430(2) ?
C4 C5 . 1.546(2) ?
C5 C6 . 1.402(2) ?
O7 H7A . 0.68(3) ?
O7 H7B . 0.81(3) ?
O8 H8A . 0.75(3) ?
O8 H8B . 0.87(3) ?
O9 H9A . 0.70(3) ?
O9 H9B . 0.82(3) ?

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
O5 Na1 O7 89.61(6) . . ?
O5 Na1 O8 166.85(6) . . ?
O7 Na1 O8 92.74(6) . . ?
O5 Na1 O2 69.25(5) . . ?
O7 Na1 O2 109.82(6) . . ?
O8 Na1 O2 97.82(5) . . ?
O5 Na1 O8 88.23(6) . 2_655 ?
O7 Na1 O8 161.73(6) . 2_655 ?
O8 Na1 O8 93.49(5) . 2_655 ?
O2 Na1 O8 86.31(5) . 2_655 ?
O5 Na1 O9 109.06(6) . 1_554 ?
O7 Na1 O9 83.12(5) . 1_554 ?
O8 Na1 O9 84.08(5) . 1_554 ?
O2 Na1 O9 166.74(6) . 1_554 ?
O8 Na1 O9 80.47(5) 2_655 1_554 ?
O5 Na1 Na1 132.74(6) . 2_655 ?
O7 Na1 Na1 137.38(5) . 2_655 ?
O8 Na1 Na1 47.50(4) . 2_655 ?
O2 Na1 Na1 92.89(5) . 2_655 ?
O8 Na1 Na1 45.99(4) 2_655 2_655 ?
O9 Na1 Na1 78.66(5) 1_554 2_655 ?
O5 Na1 Na2 109.76(5) . 1_554 ?
O7 Na1 Na2 42.27(4) . 1_554 ?
O8 Na1 Na2 80.26(4) . 1_554 ?
O2 Na1 Na2 151.27(5) . 1_554 ?
O8 Na1 Na2 122.37(4) 2_655 1_554 ?
O9 Na1 Na2 41.99(4) 1_554 1_554 ?
Na1 Na1 Na2 105.88(3) 2_655 1_554 ?
O1 Na2 O9 107.53(6) . . ?
O1 Na2 O7 109.36(6) . 1_556 ?
O9 Na2 O7 84.14(5) . 1_556 ?
O1 Na2 O3 87.26(5) . 1_545 ?
O9 Na2 O3 115.43(6) . 1_545 ?
O7 Na2 O3 149.90(6) 1_556 1_545 ?
O1 Na2 O4 153.26(6) . 1_545 ?
O9 Na2 O4 83.10(5) . 1_545 ?
O7 Na2 O4 95.87(5) 1_556 1_545 ?
O3 Na2 O4 66.14(5) 1_545 1_545 ?
O1 Na2 O1 96.15(5) . 2_556 ?
O9 Na2 O1 150.55(5) . 2_556 ?
O7 Na2 O1 71.40(5) 1_556 2_556 ?
O3 Na2 O1 82.25(5) 1_545 2_556 ?
O4 Na2 O1 83.35(5) 1_545 2_556 ?
O1 Na2 Na2 54.30(4) . 2_556 ?
O9 Na2 Na2 155.97(5) . 2_556 ?
O7 Na2 Na2 87.82(5) 1_556 2_556 ?
O3 Na2 Na2 81.83(5) 1_545 2_556 ?
O4 Na2 Na2 120.31(5) 1_545 2_556 ?
O1 Na2 Na2 41.85(3) 2_556 2_556 ?
O1 Na2 Na1 123.03(4) . 1_556 ?
O9 Na2 Na1 43.77(4) . 1_556 ?
O7 Na2 Na1 41.53(4) 1_556 1_556 ?
O3 Na2 Na1 145.14(5) 1_545 1_556 ?
O4 Na2 Na1 81.83(4) 1_545 1_556 ?
O1 Na2 Na1 108.29(4) 2_556 1_556 ?
Na2 Na2 Na1 128.47(4) 2_556 1_556 ?
O1 Na2 H9A 113.8(6) . . ?
O9 Na2 H9A 14.4(7) . . ?
O7 Na2 H9A 94.0(6) 1_556 . ?
O3 Na2 H9A 102.1(7) 1_545 . ?
O4 Na2 H9A 71.7(6) 1_545 . ?
O1 Na2 H9A 149.8(6) 2_556 . ?
Na2 Na2 H9A 167.6(6) 2_556 . ?
Na1 Na2 H9A 52.5(6) 1_556 . ?
C1 O1 Na2 145.34(13) . . ?
C1 O1 Na2 113.10(12) . 2_556 ?
Na2 O1 Na2 83.85(5) . 2_556 ?
C2 O2 Na1 135.31(11) . . ?
C4 O3 Na2 121.57(11) . 1_565 ?
C5 O4 Na2 120.05(12) . 1_565 ?
N1 O5 Na1 144.23(12) . . ?
O5 N1 O6 121.81(15) . . ?
O5 N1 C3 120.18(14) . . ?
O6 N1 C3 117.97(14) . . ?
O1 C1 C6 125.74(16) . . ?
O1 C1 C2 115.86(15) . . ?
C6 C1 C2 118.39(15) . . ?
O2 C2 C3 126.06(16) . . ?
O2 C2 C1 114.93(15) . . ?
C3 C2 C1 119.01(15) . . ?
C2 C3 C4 121.14(16) . . ?
C2 C3 N1 119.52(15) . . ?
C4 C3 N1 119.34(15) . . ?
O3 C4 C3 126.36(16) . . ?
O3 C4 C5 114.62(15) . . ?
C3 C4 C5 118.97(15) . . ?
O4 C5 C6 125.57(16) . . ?
O4 C5 C4 115.63(15) . . ?
C6 C5 C4 118.80(15) . . ?
C5 C6 C1 123.19(16) . . ?
C5 C6 Cl1 117.64(13) . . ?
C1 C6 Cl1 119.08(13) . . ?
Na1 O7 Na2 96.20(6) . 1_554 ?
Na1 O7 H7A 121(3) . . ?
Na2 O7 H7A 113(2) 1_554 . ?
Na1 O7 H7B 121.7(19) . . ?
Na2 O7 H7B 103.2(19) 1_554 . ?
H7A O7 H7B 101(3) . . ?
Na1 O8 Na1 86.51(5) . 2_655 ?
Na1 O8 H8A 110(2) . . ?
Na1 O8 H8A 121(2) 2_655 . ?
Na1 O8 H8B 137.5(18) . . ?
Na1 O8 H8B 107.0(18) 2_655 . ?
H8A O8 H8B 97(3) . . ?
Na2 O9 Na1 94.24(6) . 1_556 ?
Na2 O9 H9A 110(2) . . ?
Na1 O9 H9A 118(2) 1_556 . ?
Na2 O9 H9B 113.3(19) . . ?
Na1 O9 H9B 120.4(19) 1_556 . ?
H9A O9 H9B 101(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Na1 O5 N1 O6 -165.02(18) . . . . ?
Na1 O5 N1 C3 17.3(3) . . . . ?
Na2 O1 C1 C6 -14.0(4) . . . . ?
Na2 O1 C1 C6 100.34(19) 2_556 . . . ?
Na2 O1 C1 C2 164.99(16) . . . . ?
Na2 O1 C1 C2 -80.68(16) 2_556 . . . ?
Na1 O2 C2 C3 23.9(3) . . . . ?
Na1 O2 C2 C1 -156.94(12) . . . . ?
O1 C1 C2 O2 -5.6(2) . . . . ?
C6 C1 C2 O2 173.41(17) . . . . ?
O1 C1 C2 C3 173.61(17) . . . . ?
C6 C1 C2 C3 -7.3(2) . . . . ?
O2 C2 C3 C4 -178.90(17) . . . . ?
C1 C2 C3 C4 1.9(3) . . . . ?
O2 C2 C3 N1 0.4(3) . . . . ?
C1 C2 C3 N1 -178.73(15) . . . . ?
O5 N1 C3 C2 -18.9(3) . . . . ?
O6 N1 C3 C2 163.26(16) . . . . ?
O5 N1 C3 C4 160.42(18) . . . . ?
O6 N1 C3 C4 -17.4(2) . . . . ?
Na2 O3 C4 C3 170.71(14) 1_565 . . . ?
Na2 O3 C4 C5 -12.0(2) 1_565 . . . ?
C2 C3 C4 O3 179.87(18) . . . . ?
N1 C3 C4 O3 0.5(3) . . . . ?
C2 C3 C4 C5 2.7(3) . . . . ?
N1 C3 C4 C5 -176.70(15) . . . . ?
Na2 O4 C5 C6 -169.16(14) 1_565 . . . ?
Na2 O4 C5 C4 10.1(2) 1_565 . . . ?
O3 C4 C5 O4 1.0(2) . . . . ?
C3 C4 C5 O4 178.53(16) . . . . ?
O3 C4 C5 C6 -179.65(16) . . . . ?
C3 C4 C5 C6 -2.1(2) . . . . ?
O4 C5 C6 C1 175.70(18) . . . . ?
C4 C5 C6 C1 -3.6(3) . . . . ?
O4 C5 C6 Cl1 -0.9(3) . . . . ?
C4 C5 C6 Cl1 179.83(12) . . . . ?
O1 C1 C6 C5 -172.88(18) . . . . ?
C2 C1 C6 C5 8.2(3) . . . . ?
O1 C1 C6 Cl1 3.7(3) . . . . ?
C2 C1 C6 Cl1 -175.30(12) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_s92
_database_code_depnum_ccdc_archive 'CCDC 2048083'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2020-12-03 deposited with the CCDC.	2021-02-25 downloaded from the CCDC.
;

_audit_creation_date             2019-10-21T15:53:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum            'C12 H15 Cl1.62 Mn2 N2 O20.50'
_chemical_formula_weight         682.39

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'I 2/m'
_symmetry_space_group_name_Hall  '-I 2y'
_cell_length_a                   8.58490(10)
_cell_length_b                   16.13810(10)
_cell_length_c                   16.4897(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.5290(10)
_cell_angle_gamma                90
_cell_volume                     2264.85(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7017
_cell_measurement_theta_min      3.834
_cell_measurement_theta_max      75.802
_cell_measurement_temperature    293(2)
_exptl_crystal_density_diffrn    2.001
_exptl_crystal_F_000             1370
_exptl_absorpt_coefficient_mu    11.823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.05803
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            9867
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_theta_min         3.849
_diffrn_reflns_theta_max         76.382
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   difmap

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             2437
_reflns_number_gt                2405
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0715
_refine_ls_wR_factor_ref         0.1714
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.164
_refine_ls_number_reflns         2437
_refine_ls_number_parameters     238
_refine_ls_number_restraints     22
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0184P)²+51.6743P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.716
_refine_diff_density_min         -1.151
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
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 0 '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'
Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Mn1 0.29634(15) 0 0.50067(7) 0.0149(3) Uani d 1 . . Mn
Mn2 0.16840(16) 0.5 0.62917(8) 0.0183(3) Uani d 1 . . Mn
Cl1A 0.0549(4) 0.1883(2) 0.71146(19) 0.0293(9) Uani d 0.587(8) A 1 Cl
O5A 0.4420(8) 0.2656(4) 0.3891(4) 0.0223(17) Uani d 0.587(8) A 1 O
O6A 0.2923(11) 0.3714(5) 0.3796(5) 0.035(2) Uani d 0.587(8) A 1 O
N1A 0.343(4) 0.3087(16) 0.4136(16) 0.0308(15) Uani d 0.587(8) A 1 N
O6B 0.0834(13) 0.1317(7) 0.7302(6) 0.027(3) Uani d 0.413(8) A 2 O
O5B -0.0843(12) 0.2272(7) 0.7002(7) 0.026(3) Uani d 0.413(8) A 2 O
N1B 0.035(2) 0.1906(12) 0.6911(10) 0.0293(9) Uani d 0.413(8) A 2 N
Cl1B 0.3351(13) 0.3098(6) 0.3990(5) 0.0308(15) Uani d 0.413(8) A 2 Cl
O1 0.1935(5) 0.0852(3) 0.5870(3) 0.0254(9) Uani d 1 . . O
O2 0.3230(5) 0.1370(3) 0.4629(2) 0.0209(9) Uani d 1 . . O
O3 0.2043(6) 0.4127(3) 0.5256(3) 0.0283(10) Uani d 1 . . O
O4 0.1054(5) 0.3613(3) 0.6587(2) 0.0214(9) Uani d 1 . . O
O7 0.5183(6) 0 0.5890(3) 0.0156(11) Uani d 1 . . O
H7A 0.511(7) -0.043(3) 0.626(3) 0.019 Uiso d 1 . . H
O8 0.1030(7) 0 0.4078(4) 0.0277(14) Uani d 1 . . O
H8A -0.006(3) 0 0.411(5) 0.033 Uiso d 1 . . H
H8B 0.115(10) 0 0.3517(19) 0.033 Uiso d 1 . . H
O9 -0.0851(7) 0.5 0.6167(4) 0.0237(13) Uani d 1 . . O
O10 0.4198(10) 0.5 0.6412(6) 0.087(4) Uani d 1 . . O
H10A 0.484(7) 0.535(6) 0.678(4) 0.104 Uiso d 1 . . H
O11 0.2010(8) 0.5 0.7625(4) 0.0245(13) Uani d 1 . . O
H11A 0.257(7) 0.542(3) 0.794(4) 0.029 Uiso d 1 . . H
C1 0.1921(7) 0.1619(4) 0.5768(3) 0.0191(11) Uani d 1 . . C
C2 0.2669(6) 0.1913(4) 0.5011(3) 0.0161(11) Uani d 1 . . C
C3 0.2653(7) 0.2781(4) 0.4840(4) 0.0208(12) Uani d 1 . . C
C4 0.2071(7) 0.3369(4) 0.5355(4) 0.0193(11) Uani d 1 . . C
C5 0.1426(7) 0.3065(4) 0.6128(3) 0.0178(11) Uani d 1 . . C
C6 0.1289(7) 0.2201(4) 0.6261(4) 0.0222(12) Uani d 1 . . C
H9A -0.142(7) 0.544(3) 0.590(4) 0.027 Uiso d 1 . . H
O12 0.5 0.5 0.5 0.089(5) Uani d 1 . . O
O13 0.1797(8) 0 0.2563(4) 0.0341(16) Uani d 1 . . O
H13A 0.247(8) 0.045(3) 0.250(5) 0.041 Uiso d 1 . . H
O14 0.5737(6) -0.1193(3) 0.7038(3) 0.0311(11) Uani d 1 . . O
H14A 0.568(8) -0.1713(18) 0.678(3) 0.037 Uiso d 1 . . H
H14B 0.510(8) -0.125(4) 0.746(3) 0.037 Uiso d 1 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Mn1 O8 . 2.106(6) ?
Mn1 O7 . 2.242(6) ?
Mn1 O1 6 2.242(4) ?
Mn1 O1 . 2.242(4) ?
Mn1 O7 5_656 2.310(5) ?
Mn1 O2 . 2.317(4) ?
Mn1 O2 6 2.317(4) ?
Mn2 O10 . 2.141(9) ?
Mn2 O9 . 2.159(6) ?
Mn2 O11 . 2.179(6) ?
Mn2 O3 6_565 2.266(5) ?
Mn2 O3 . 2.266(5) ?
Mn2 O4 . 2.368(4) ?
Mn2 O4 6_565 2.368(4) ?
Cl1A C6 . 1.698(6) ?
O5A N1A . 1.211(16) ?
O6A N1A . 1.209(16) ?
N1A C3 . 1.494(16) ?
O6B N1B . 1.194(16) ?
O5B N1B . 1.206(16) ?
N1B C6 . 1.502(16) ?
Cl1B C3 . 1.674(8) ?
O1 C1 . 1.248(8) ?
O2 C2 . 1.214(7) ?
O3 C4 . 1.234(8) ?
O4 C5 . 1.233(7) ?
O7 H7A . 0.94(2) ?
O8 H8A . 0.95(2) ?
O8 H8B . 0.94(2) ?
O9 H9A . 0.94(2) ?
O10 H10A . 0.95(2) ?
O11 H11A . 0.95(2) ?
C1 C6 . 1.398(8) ?
C1 C2 . 1.551(7) ?
C2 C3 . 1.429(8) ?
C3 C4 . 1.408(8) ?
C4 C5 . 1.536(8) ?
C5 C6 . 1.418(8) ?
O13 H13A . 0.95(2) ?
O14 H14A . 0.94(2) ?
O14 H14B . 0.94(2) ?

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
O8 Mn1 O7 174.0(2) . . ?
O8 Mn1 O1 97.08(18) . 6 ?
O7 Mn1 O1 87.67(16) . 6 ?
O8 Mn1 O1 97.08(18) . . ?
O7 Mn1 O1 87.67(16) . . ?
O1 Mn1 O1 75.7(2) 6 . ?
O8 Mn1 O7 94.5(2) . 5_656 ?
O7 Mn1 O7 79.5(2) . 5_656 ?
O1 Mn1 O7 140.19(12) 6 5_656 ?
O1 Mn1 O7 140.19(12) . 5_656 ?
O8 Mn1 O2 84.31(12) . . ?
O7 Mn1 O2 93.96(12) . . ?
O1 Mn1 O2 144.78(15) 6 . ?
O1 Mn1 O2 69.26(14) . . ?
O7 Mn1 O2 74.19(10) 5_656 . ?
O8 Mn1 O2 84.31(12) . 6 ?
O7 Mn1 O2 93.96(12) . 6 ?
O1 Mn1 O2 69.26(14) 6 6 ?
O1 Mn1 O2 144.78(15) . 6 ?
O7 Mn1 O2 74.19(10) 5_656 6 ?
O2 Mn1 O2 145.3(2) . 6 ?
O10 Mn2 O9 179.9(3) . . ?
O10 Mn2 O11 84.9(3) . . ?
O9 Mn2 O11 95.2(2) . . ?
O10 Mn2 O3 80.5(2) . 6_565 ?
O9 Mn2 O3 99.41(18) . 6_565 ?
O11 Mn2 O3 138.42(13) . 6_565 ?
O10 Mn2 O3 80.5(2) . . ?
O9 Mn2 O3 99.41(18) . . ?
O11 Mn2 O3 138.42(13) . . ?
O3 Mn2 O3 76.9(2) 6_565 . ?
O10 Mn2 O4 103.61(12) . . ?
O9 Mn2 O4 76.42(11) . . ?
O11 Mn2 O4 78.19(11) . . ?
O3 Mn2 O4 143.11(15) 6_565 . ?
O3 Mn2 O4 67.95(15) . . ?
O10 Mn2 O4 103.61(12) . 6_565 ?
O9 Mn2 O4 76.42(11) . 6_565 ?
O11 Mn2 O4 78.19(11) . 6_565 ?
O3 Mn2 O4 67.95(15) 6_565 6_565 ?
O3 Mn2 O4 143.11(15) . 6_565 ?
O4 Mn2 O4 141.9(2) . 6_565 ?
O6A N1A O5A 123.4(14) . . ?
O6A N1A C3 118.0(13) . . ?
O5A N1A C3 118.3(13) . . ?
O6B N1B O5B 124.4(16) . . ?
O6B N1B C6 117.0(14) . . ?
O5B N1B C6 118.5(13) . . ?
C1 O1 Mn1 121.3(4) . . ?
C2 O2 Mn1 119.3(4) . . ?
C4 O3 Mn2 121.2(4) . . ?
C5 O4 Mn2 117.9(4) . . ?
Mn1 O7 Mn1 100.5(2) . 5_656 ?
Mn1 O7 H7A 108(4) . . ?
Mn1 O7 H7A 122(4) 5_656 . ?
Mn1 O8 H8A 131(5) . . ?
Mn1 O8 H8B 122(5) . . ?
H8A O8 H8B 107(4) . . ?
Mn2 O9 H9A 120(4) . . ?
Mn2 O10 H10A 124(4) . . ?
Mn2 O11 H11A 123(4) . . ?
O1 C1 C6 125.9(6) . . ?
O1 C1 C2 114.4(5) . . ?
C6 C1 C2 119.7(5) . . ?
O2 C2 C3 126.8(5) . . ?
O2 C2 C1 115.5(5) . . ?
C3 C2 C1 117.7(5) . . ?
C4 C3 C2 122.4(5) . . ?
C4 C3 N1A 118.3(11) . . ?
C2 C3 N1A 118.9(10) . . ?
C4 C3 Cl1B 119.5(6) . . ?
C2 C3 Cl1B 118.0(5) . . ?
O3 C4 C3 126.2(6) . . ?
O3 C4 C5 115.1(5) . . ?
C3 C4 C5 118.7(5) . . ?
O4 C5 C6 125.2(5) . . ?
O4 C5 C4 115.5(5) . . ?
C6 C5 C4 119.3(5) . . ?
C1 C6 C5 121.7(5) . . ?
C1 C6 N1B 119.2(9) . . ?
C5 C6 N1B 119.0(8) . . ?
C1 C6 Cl1A 119.6(5) . . ?
C5 C6 Cl1A 118.3(4) . . ?
H14A O14 H14B 105(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Mn1 O1 C1 C6 178.9(5) . . . . ?
Mn1 O1 C1 C2 -0.2(7) . . . . ?
Mn1 O2 C2 C3 -176.6(5) . . . . ?
Mn1 O2 C2 C1 4.4(6) . . . . ?
O1 C1 C2 O2 -2.8(8) . . . . ?
C6 C1 C2 O2 178.0(5) . . . . ?
O1 C1 C2 C3 178.1(5) . . . . ?
C6 C1 C2 C3 -1.1(8) . . . . ?
O2 C2 C3 C4 -175.3(6) . . . . ?
C1 C2 C3 C4 3.7(9) . . . . ?
O2 C2 C3 N1A -1.6(19) . . . . ?
C1 C2 C3 N1A 177.4(17) . . . . ?
O2 C2 C3 Cl1B 4.9(10) . . . . ?
C1 C2 C3 Cl1B -176.1(6) . . . . ?
O6A N1A C3 C4 -35(4) . . . . ?
O5A N1A C3 C4 152(2) . . . . ?
O6A N1A C3 C2 151(2) . . . . ?
O5A N1A C3 C2 -22(4) . . . . ?
Mn2 O3 C4 C3 -163.5(5) . . . . ?
Mn2 O3 C4 C5 15.4(7) . . . . ?
C2 C3 C4 O3 178.7(6) . . . . ?
N1A C3 C4 O3 5.0(18) . . . . ?
Cl1B C3 C4 O3 -1.5(10) . . . . ?
C2 C3 C4 C5 -0.2(9) . . . . ?
N1A C3 C4 C5 -173.9(16) . . . . ?
Cl1B C3 C4 C5 179.6(7) . . . . ?
Mn2 O4 C5 C6 173.1(5) . . . . ?
Mn2 O4 C5 C4 -7.5(6) . . . . ?
O3 C4 C5 O4 -4.7(8) . . . . ?
C3 C4 C5 O4 174.4(5) . . . . ?
O3 C4 C5 C6 174.8(6) . . . . ?
C3 C4 C5 C6 -6.1(8) . . . . ?
O1 C1 C6 C5 175.6(6) . . . . ?
C2 C1 C6 C5 -5.3(9) . . . . ?
O1 C1 C6 N1B -8.6(12) . . . . ?
C2 C1 C6 N1B 170.5(9) . . . . ?
O1 C1 C6 Cl1A 3.8(9) . . . . ?
C2 C1 C6 Cl1A -177.1(4) . . . . ?
O4 C5 C6 C1 -171.6(6) . . . . ?
C4 C5 C6 C1 8.9(9) . . . . ?
O4 C5 C6 N1B 12.5(12) . . . . ?
C4 C5 C6 N1B -166.9(9) . . . . ?
O4 C5 C6 Cl1A 0.2(9) . . . . ?
C4 C5 C6 Cl1A -179.2(4) . . . . ?
O6B N1B C6 C1 41.9(18) . . . . ?
O5B N1B C6 C1 -137.8(14) . . . . ?
O6B N1B C6 C5 -142.2(13) . . . . ?
O5B N1B C6 C5 38.1(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
_geom_hbond_publ_flag
O7 H7A O14 0.94(2) 1.80(3) 2.698(6) 159(6) . yes
O8 H8A O1 0.95(2) 2.118(17) 2.904(7) 139.5(5) 5_556 yes
O8 H8A O1 0.95(2) 2.118(17) 2.904(7) 139.5(5) 2_556 yes
O8 H8B O13 0.94(2) 1.73(3) 2.666(9) 168(8) . yes
O9 H9A O6A^a 0.94(2) 1.99(5) 2.739(9) 135(6) 5_566 yes
O9 H9A Cl1B^b 0.94(2) 2.91(4) 3.735(8) 148(6) 5_566 yes
O9 H9A O3 0.94(2) 2.03(5) 2.812(7) 140(6) 5_566 yes
O10 H10A O6B^b 0.95(2) 2.30(6) 3.004(13) 130(5) 4_556 yes
O10 H10A O13 0.95(2) 2.06(9) 2.734(11) 127(9) 3 yes
O11 H11A Cl1A^a 0.95(2) 2.87(4) 3.684(5) 145(6) 4_556 yes
O11 H11A O6B^b 0.95(2) 2.07(5) 2.811(12) 134(6) 4_556 yes
O11 H11A O1 0.95(2) 2.07(5) 2.878(7) 142(6) 4_556 yes
O13 H13A O6A^a 0.95(2) 2.51(7) 3.087(9) 120(6) 7 yes
O13 H13A O14 0.95(2) 2.02(5) 2.873(7) 149(7) 5_656 yes
O14 H14A O5A^a 0.94(2) 1.88(2) 2.808(9) 171(5) 5_656 yes
O14 H14A O2 0.94(2) 2.67(6) 3.012(6) 102(4) 5_656 yes
O14 H14A O5B^b 0.94(2) 2.58(5) 2.934(12) 103(4) 4_546 yes
O14 H14B O4 0.94(2) 1.98(2) 2.918(6) 174(7) 4_546 yes



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_s268
_database_code_depnum_ccdc_archive 'CCDC 2048080'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2020-12-03 deposited with the CCDC.	2021-02-25 downloaded from the CCDC.
;

_audit_creation_date             2019-10-21T15:01:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum            'C16 H8 Cl Cu N3 O6'
_chemical_formula_moiety         'C16 H8 Cl Cu N3 O6'
_chemical_formula_weight         437.24

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   8.0984(3)
_cell_length_b                   8.4893(4)
_cell_length_c                   12.7713(7)
_cell_angle_alpha                107.918(4)
_cell_angle_beta                 106.289(4)
_cell_angle_gamma                92.918(3)
_cell_volume                     792.80(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4481
_cell_measurement_theta_min      5.547
_cell_measurement_theta_max      75.912
_cell_measurement_temperature    293(2)
_exptl_crystal_description       plate
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_F_000             438
_exptl_absorpt_coefficient_mu    3.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.37899
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            6581
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_theta_min         5.54
_diffrn_reflns_theta_max         76.306
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             3257
_reflns_number_gt                3057
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.034
_refine_ls_wR_factor_ref         0.0925
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.052
_refine_ls_number_reflns         3257
_refine_ls_number_parameters     263
_refine_ls_number_restraints     15
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+0.3607P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
Cu Cu -1.9646 0.5888 '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'

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cu1 0.36223(4) 0.56585(3) 0.08691(2) 0.03342(11) Uani d 1 . . Cu
Cl1A 0.30653(11) -0.03156(8) -0.12094(7) 0.0480(2) Uani d 0.912(3) A 1 Cl
O5A -0.1687(4) 0.4872(3) -0.3466(2) 0.0749(7) Uani d 0.912(3) A 1 O
O6A -0.1626(2) 0.5783(2) -0.16851(18) 0.0510(5) Uani d 0.912(3) A 1 O
N1A -0.1197(4) 0.4839(5) -0.2495(3) 0.0457(7) Uani d 0.912(3) A 1 N
Cl1B -0.1341(13) 0.5329(14) -0.2466(11) 0.0457(7) Uani d 0.088(3) A 2 Cl
O5B 0.395(3) 0.000(3) -0.094(3) 0.061(5) Uani d 0.088(3) A 2 O
O6B 0.144(3) -0.140(2) -0.151(2) 0.061(5) Uani d 0.088(3) A 2 O
N1B 0.242(3) -0.025(3) -0.132(3) 0.0480(2) Uani d 0.088(3) A 2 N
O1 0.17219(19) 0.55611(17) -0.04788(12) 0.0386(3) Uani d 1 . . O
O2 0.3672(2) 0.33736(18) -0.00230(12) 0.0404(3) Uani d 1 . . O
O3 0.0204(3) -0.0790(2) -0.34122(16) 0.0596(5) Uani d 1 . . O
O4 -0.1786(2) 0.1477(2) -0.39454(15) 0.0570(5) Uani d 1 . . O
N2 0.3699(2) 0.8017(2) 0.17588(14) 0.0324(3) Uani d 1 . . N
N3 0.5442(2) 0.5749(2) 0.22854(14) 0.0319(3) Uani d 1 . . N
C1 0.1241(2) 0.4096(2) -0.12169(17) 0.0310(4) Uani d 1 . . C
C2 0.2330(2) 0.2797(2) -0.09342(16) 0.0315(4) Uani d 1 . . C
C3 0.1869(3) 0.1158(2) -0.16217(17) 0.0342(4) Uani d 1 . . C
C4 0.0520(3) 0.0629(3) -0.27268(18) 0.0391(4) Uani d 1 . . C
C5 -0.0574(3) 0.1962(3) -0.30488(17) 0.0383(4) Uani d 1 . . C
C6 -0.0134(3) 0.3634(3) -0.22402(17) 0.0347(4) Uani d 1 . . C
C7 0.2706(3) 0.9065(3) 0.13839(19) 0.0397(4) Uani d 1 . . C
H7 0.18842 0.867064 0.065164 0.048 Uiso calc 1 . . H
C8 0.2873(3) 1.0721(3) 0.2060(2) 0.0468(5) Uani d 1 . . C
H8 0.216724 1.143425 0.179058 0.056 Uiso calc 1 . . H
C9 0.4098(3) 1.1295(3) 0.3137(2) 0.0461(5) Uani d 1 . . C
H9 0.422475 1.240564 0.360358 0.055 Uiso calc 1 . . H
C10 0.5144(3) 1.0224(3) 0.35285(19) 0.0409(5) Uani d 1 . . C
H10 0.598596 1.060416 0.425281 0.049 Uiso calc 1 . . H
C11 0.4907(2) 0.8569(2) 0.28146(17) 0.0319(4) Uani d 1 . . C
C12 0.5891(2) 0.7266(2) 0.31210(16) 0.0315(4) Uani d 1 . . C
C13 0.7161(3) 0.7519(3) 0.41675(18) 0.0403(5) Uani d 1 . . C
H13 0.748301 0.857137 0.473644 0.048 Uiso calc 1 . . H
C14 0.7939(3) 0.6171(3) 0.4347(2) 0.0459(5) Uani d 1 . . C
H14 0.879159 0.631487 0.504498 0.055 Uiso calc 1 . . H
C15 0.7459(3) 0.4616(3) 0.3498(2) 0.0457(5) Uani d 1 . . C
H15 0.796707 0.370025 0.361524 0.055 Uiso calc 1 . . H
C16 0.6199(3) 0.4455(3) 0.24653(19) 0.0385(4) Uani d 1 . . C
H16 0.5872 0.341621 0.18812 0.046 Uiso calc 1 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O2 . 1.9329(14) ?
Cu1 O1 . 1.9371(14) ?
Cu1 N2 . 1.9624(16) ?
Cu1 N3 . 1.9639(16) ?
Cl1A C3 . 1.738(2) ?
O5A N1A . 1.201(4) ?
O6A N1A . 1.246(4) ?
N1A C6 . 1.425(4) ?
Cl1B C6 . 1.831(10) ?
O5B N1B . 1.175(18) ?
O6B N1B . 1.140(18) ?
N1B C3 . 1.421(17) ?
O1 C1 . 1.269(2) ?
O2 C2 . 1.289(2) ?
O3 C4 . 1.215(3) ?
O4 C5 . 1.218(3) ?
N2 C7 . 1.337(3) ?
N2 C11 . 1.349(3) ?
N3 C16 . 1.334(3) ?
N3 C12 . 1.349(2) ?
C1 C6 . 1.387(3) ?
C1 C2 . 1.513(3) ?
C2 C3 . 1.363(3) ?
C3 C4 . 1.443(3) ?
C4 C5 . 1.555(3) ?
C5 C6 . 1.431(3) ?
C7 C8 . 1.381(3) ?
C7 H7 . 0.93 ?
C8 C9 . 1.373(4) ?
C8 H8 . 0.93 ?
C9 C10 . 1.384(3) ?
C9 H9 . 0.93 ?
C10 C11 . 1.389(3) ?
C10 H10 . 0.93 ?
C11 C12 . 1.480(3) ?
C12 C13 . 1.386(3) ?
C13 C14 . 1.383(3) ?
C13 H13 . 0.93 ?
C14 C15 . 1.379(3) ?
C14 H14 . 0.93 ?
C15 C16 . 1.386(3) ?
C15 H15 . 0.93 ?
C16 H16 . 0.93 ?

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
O2 Cu1 O1 84.19(6) . . ?
O2 Cu1 N2 176.64(7) . . ?
O1 Cu1 N2 96.80(6) . . ?
O2 Cu1 N3 96.78(6) . . ?
O1 Cu1 N3 176.43(7) . . ?
N2 Cu1 N3 82.43(7) . . ?
O5A N1A O6A 123.0(3) . . ?
O5A N1A C6 119.9(3) . . ?
O6A N1A C6 117.1(3) . . ?
O6B N1B O5B 131(2) . . ?
O6B N1B C3 121(2) . . ?
O5B N1B C3 107.7(19) . . ?
C1 O1 Cu1 112.70(12) . . ?
C2 O2 Cu1 111.80(12) . . ?
C7 N2 C11 120.13(17) . . ?
C7 N2 Cu1 125.29(14) . . ?
C11 N2 Cu1 114.55(13) . . ?
C16 N3 C12 120.16(17) . . ?
C16 N3 Cu1 125.32(13) . . ?
C12 N3 Cu1 114.51(13) . . ?
O1 C1 C6 125.55(18) . . ?
O1 C1 C2 115.02(16) . . ?
C6 C1 C2 119.40(17) . . ?
O2 C2 C3 124.79(18) . . ?
O2 C2 C1 114.89(16) . . ?
C3 C2 C1 120.32(17) . . ?
C2 C3 N1B 126.8(12) . . ?
C2 C3 C4 122.03(18) . . ?
N1B C3 C4 110.6(11) . . ?
C2 C3 Cl1A 118.83(15) . . ?
C4 C3 Cl1A 118.92(15) . . ?
O3 C4 C3 123.6(2) . . ?
O3 C4 C5 118.82(19) . . ?
C3 C4 C5 117.63(17) . . ?
O4 C5 C6 125.4(2) . . ?
O4 C5 C4 117.0(2) . . ?
C6 C5 C4 117.50(17) . . ?
C1 C6 N1A 119.7(2) . . ?
C1 C6 C5 122.48(18) . . ?
N1A C6 C5 117.8(2) . . ?
C1 C6 Cl1B 114.7(4) . . ?
C5 C6 Cl1B 122.9(5) . . ?
N2 C7 C8 121.5(2) . . ?
N2 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 118.9(2) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 120.1(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C11 118.5(2) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
N2 C11 C10 120.95(18) . . ?
N2 C11 C12 114.20(16) . . ?
C10 C11 C12 124.84(18) . . ?
N3 C12 C13 120.92(18) . . ?
N3 C12 C11 114.23(16) . . ?
C13 C12 C11 124.84(18) . . ?
C14 C13 C12 118.54(19) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C15 C14 C13 120.40(19) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 118.1(2) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
N3 C16 C15 121.84(19) . . ?
N3 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 C6 177.12(17) . . . . ?
Cu1 O1 C1 C2 -4.7(2) . . . . ?
Cu1 O2 C2 C3 -168.85(17) . . . . ?
Cu1 O2 C2 C1 11.2(2) . . . . ?
O1 C1 C2 O2 -4.5(3) . . . . ?
C6 C1 C2 O2 173.79(19) . . . . ?
O1 C1 C2 C3 175.54(19) . . . . ?
C6 C1 C2 C3 -6.1(3) . . . . ?
O2 C2 C3 N1B 19.4(14) . . . . ?
C1 C2 C3 N1B -160.7(14) . . . . ?
O2 C2 C3 C4 -169.9(2) . . . . ?
C1 C2 C3 C4 10.0(3) . . . . ?
O2 C2 C3 Cl1A 4.7(3) . . . . ?
C1 C2 C3 Cl1A -175.42(15) . . . . ?
O6B N1B C3 C2 133(3) . . . . ?
O5B N1B C3 C2 -51(3) . . . . ?
O6B N1B C3 C4 -39(4) . . . . ?
O5B N1B C3 C4 137(3) . . . . ?
C2 C3 C4 O3 172.0(2) . . . . ?
N1B C3 C4 O3 -16.0(13) . . . . ?
Cl1A C3 C4 O3 -2.6(3) . . . . ?
C2 C3 C4 C5 -7.8(3) . . . . ?
N1B C3 C4 C5 164.3(13) . . . . ?
Cl1A C3 C4 C5 177.68(15) . . . . ?
O3 C4 C5 O4 5.2(3) . . . . ?
C3 C4 C5 O4 -175.0(2) . . . . ?
O3 C4 C5 C6 -178.0(2) . . . . ?
C3 C4 C5 C6 1.7(3) . . . . ?
O1 C1 C6 N1A -3.8(3) . . . . ?
C2 C1 C6 N1A 178.12(19) . . . . ?
O1 C1 C6 C5 178.3(2) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
O1 C1 C6 Cl1B -2.1(4) . . . . ?
C2 C1 C6 Cl1B 179.8(2) . . . . ?
O5A N1A C6 C1 140.1(3) . . . . ?
O6A N1A C6 C1 -42.4(4) . . . . ?
O5A N1A C6 C5 -41.8(4) . . . . ?
O6A N1A C6 C5 135.7(3) . . . . ?
O4 C5 C6 C1 178.3(2) . . . . ?
C4 C5 C6 C1 1.8(3) . . . . ?
O4 C5 C6 N1A 0.2(4) . . . . ?
C4 C5 C6 N1A -176.18(19) . . . . ?
O4 C5 C6 Cl1B -1.4(4) . . . . ?
C4 C5 C6 Cl1B -177.8(3) . . . . ?
C11 N2 C7 C8 -0.5(3) . . . . ?
Cu1 N2 C7 C8 -178.54(17) . . . . ?
N2 C7 C8 C9 0.5(4) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C8 C9 C10 C11 -0.7(4) . . . . ?
C7 N2 C11 C10 0.0(3) . . . . ?
Cu1 N2 C11 C10 178.17(16) . . . . ?
C7 N2 C11 C12 179.15(18) . . . . ?
Cu1 N2 C11 C12 -2.7(2) . . . . ?
C9 C10 C11 N2 0.6(3) . . . . ?
C9 C10 C11 C12 -178.4(2) . . . . ?
C16 N3 C12 C13 1.2(3) . . . . ?
Cu1 N3 C12 C13 -179.83(16) . . . . ?
C16 N3 C12 C11 -178.21(18) . . . . ?
Cu1 N3 C12 C11 0.8(2) . . . . ?
N2 C11 C12 N3 1.3(3) . . . . ?
C10 C11 C12 N3 -179.6(2) . . . . ?
N2 C11 C12 C13 -178.14(19) . . . . ?
C10 C11 C12 C13 1.0(3) . . . . ?
N3 C12 C13 C14 -1.2(3) . . . . ?
C11 C12 C13 C14 178.1(2) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C13 C14 C15 C16 0.7(4) . . . . ?
C12 N3 C16 C15 -0.2(3) . . . . ?
Cu1 N3 C16 C15 -179.06(18) . . . . ?
C14 C15 C16 N3 -0.7(4) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_cu-cl4q-1
_database_code_depnum_ccdc_archive 'CCDC 2048081'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2020-12-03 deposited with the CCDC.	2021-02-25 downloaded from the CCDC.
;

_audit_creation_date             2020-11-24T10:43:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA


_chemical_formula_sum            'C24 H14 Cl3 Cu3 N6 O21'
_chemical_formula_moiety         '2(C8 H5 Cl Cu N2 O7), C8 H4 Cl Cu N2 O7'
_chemical_formula_weight         1019.41

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/m'
_symmetry_space_group_name_Hall  '-P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,1/2+y,-z
3 -x,-y,-z
4 x,1/2-y,z

_cell_length_a                   10.2663(5)
_cell_length_b                   15.8719(6)
_cell_length_c                   10.3474(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.549(4)
_cell_angle_gamma                90
_cell_volume                     1685.99(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    876
_cell_measurement_theta_min      4.2694
_cell_measurement_theta_max      75.6487
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            red-brown
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    2.008
_exptl_crystal_F_000             1012
_exptl_absorpt_coefficient_mu    5.305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.02527
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            4888
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.2003
_diffrn_reflns_theta_min         4.273
_diffrn_reflns_theta_max         75.835
_diffrn_reflns_theta_full        67.5
_diffrn_measured_fraction_theta_max 0.831
_diffrn_measured_fraction_theta_full 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.952
_diffrn_reflns_Laue_measured_fraction_max 0.831
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   mixed

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             3014
_reflns_number_gt                998
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1256
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.2013
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      0.995
_refine_ls_number_reflns         3014
_refine_ls_number_parameters     324
_refine_ls_number_restraints     211
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0796P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.005
_refine_diff_density_max         0.772
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009 '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'
O O 0.049 0.032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.333 0.557 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.965 0.589 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.364 0.702 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.031 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cu1 0.20780(17) 0.25 0.19397(14) 0.0365(4) Uani d 1 . . Cu
Cu2 0.12539(17) -0.25 0.13965(15) 0.0366(4) Uani d 1 . . Cu
Cl1B -0.1393(5) 0.0196(6) 0.1595(7) 0.044 Uani d 0.5 . . Cl
Cl1A 0.4724(6) -0.0210(10) 0.1736(14) 0.0429(9) Uani d 0.5 . . Cl
N1A -0.1168(14) 0.017(2) 0.157(2) 0.044 Uani d 0.5 . . N
N1B 0.451(2) -0.019(4) 0.173(5) 0.0429(9) Uani d 0.5 . . N
O1 0.3146(6) 0.1382(4) 0.1976(5) 0.0428(14) Uani d 1 . . O
O2 0.0610(6) 0.1554(4) 0.1865(5) 0.0458(15) Uani d 1 . . O
O3 0.0196(6) -0.1367(4) 0.1368(5) 0.0490(15) Uani d 1 . . O
O4 0.2712(5) -0.1541(4) 0.1472(5) 0.0409(14) Uani d 1 . . O
O5A -0.1721(14) 0.0817(12) 0.1374(16) 0.080(4) Uani d 0.5 . . O
O5B 0.5078(16) -0.0850(11) 0.2007(14) 0.077(4) Uani d 0.5 . . O
O6A -0.1878(18) -0.0440(14) 0.188(2) 0.104(6) Uani d 0.5 . . O
O6B 0.5223(18) 0.0454(13) 0.153(2) 0.109 Uani d 0.5 . . O
O11 0.1260(9) -0.25 -0.0529(8) 0.046(2) Uani d 1 . . O
H11A 0.070(6) -0.208(3) -0.085(5) 0.055 Uiso d 1 . . H
O12 0.2073(8) 0.25 0.3869(6) 0.039(2) Uani d 1 . . O
H12B 0.256(6) 0.205(3) 0.425(3) 0.047 Uiso d 1 . . H
N4 0.1102(10) -0.25 0.3328(8) 0.051(3) Uani d 1 . . N
N5 0.2195(10) 0.25 -0.0006(12) 0.055(3) Uani d 1 . . N
C1 0.2517(8) 0.0708(5) 0.1808(7) 0.0355(17) Uani d 1 . . C
C2 0.1029(9) 0.0821(5) 0.1774(7) 0.0393(18) Uani d 1 . . C
C3 0.0239(7) 0.0090(5) 0.1639(7) 0.0354(17) Uani d 1 . . C
C4 0.0837(10) -0.0723(6) 0.1532(8) 0.0443(19) Uani d 1 . . C
C5 0.2295(9) -0.0815(5) 0.1583(7) 0.0366(17) Uani d 1 . . C
C6 0.3095(8) -0.0084(5) 0.1685(7) 0.0397(18) Uani d 1 . . C
C10 0.1128(11) -0.25 0.4398(9) 0.047(4) Uani d 1 . . C
C11 0.1075(12) -0.25 0.5807(14) 0.078(6) Uani d 1 . . C
H11C 0.022(3) -0.25 0.606(5) 0.117 Uiso d 1 . . H
H11D 0.138(7) -0.201(4) 0.618(5) 0.117 Uiso d 1 . . H
C12 0.2221(14) 0.25 -0.1077(13) 0.055(4) Uani d 1 . . C
C13 0.2268(14) 0.25 -0.2495(10) 0.078(7) Uani d 1 . . C
H13C 0.311(3) 0.25 -0.277(5) 0.117 Uiso d 1 . . H
H13D 0.190(6) 0.203(4) -0.285(5) 0.117 Uiso d 1 . . H
Cu3 0.45897(17) 0.75 0.47305(15) 0.0358(4) Uani d 1 . . Cu
Cl2 0.1946(5) 1.0208(5) 0.4938(4) 0.0454(9) Uani d 0.5 . . Cl
N2 0.2184(16) 1.0158(15) 0.4942(11) 0.0454(9) Uani d 0.5 . . N
N6 0.4453(10) 0.75 0.6672(9) 0.041(2) Uani d 1 . . N
O7 0.6057(6) 0.8458(4) 0.4798(5) 0.0430(14) Uani d 1 . . O
O8 0.3518(6) 0.8624(4) 0.4703(5) 0.0473(14) Uani d 1 . . O
O9 0.1425(14) 0.9558(11) 0.5140(18) 0.084(4) Uani d 0.5 . . O
O10 0.1619(15) 1.0812(11) 0.4642(14) 0.070(4) Uani d 0.5 . . O
O13 0.4568(7) 0.75 0.2804(8) 0.0376(18) Uani d 1 . . O
H13A 0.427(14) 0.796(4) 0.232(5) 0.045 Uiso d 0.5 . . H
C8 0.4147(8) 0.9291(5) 0.4844(7) 0.0342(15) Uani d 1 . . C
C7 0.5639(9) 0.9204(5) 0.4888(7) 0.0373(16) Uani d 1 . . C
C9 0.3590(8) 1.0100(6) 0.4981(7) 0.0430(18) Uani d 1 . . C
C14 0.4460(11) 0.75 0.7767(12) 0.044(3) Uani d 1 . . C
C15 0.4389(16) 0.75 0.9191(13) 0.082(6) Uani d 1 . . C
H15A 0.50164 0.711022 0.953758 0.123 Uiso calc 0.5 . . H
H15B 0.353097 0.733441 0.945086 0.123 Uiso calc 0.5 . . H
H15C 0.457349 0.805537 0.951172 0.123 Uiso calc 0.5 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O12 . 1.997(7) ?
Cu1 N5 . 2.018(13) ?
Cu1 O1 . 2.086(6) ?
Cu1 O2 . 2.129(6) ?
Cu2 O11 . 1.993(8) ?
Cu2 N4 . 2.006(9) ?
Cu2 O3 . 2.101(6) ?
Cu2 O4 . 2.136(6) ?
Cl1B O5A . 1.07(2) ?
Cl1B O6A . 1.16(2) ?
Cl1B C3 . 1.684(8) ?
Cl1A O5B . 1.11(2) ?
Cl1A O6B . 1.19(3) ?
Cl1A C6 . 1.685(10) ?
N1A O5A . 1.18(3) ?
N1A O6A . 1.26(3) ?
N1A C3 . 1.452(15) ?
N1B O5B . 1.24(5) ?
N1B O6B . 1.27(6) ?
N1B C6 . 1.459(19) ?
O1 C1 . 1.261(9) ?
O2 C2 . 1.243(10) ?
O3 C4 . 1.227(11) ?
O4 C5 . 1.235(9) ?
O11 H11A . 0.94(2) ?
O12 H12B . 0.95(2) ?
N4 C10 . 1.108(12) ?
N5 C12 . 1.109(15) ?
C1 C6 . 1.396(11) ?
C1 C2 . 1.539(11) ?
C2 C3 . 1.422(11) ?
C3 C4 . 1.434(12) ?
C4 C5 . 1.504(12) ?
C5 C6 . 1.425(11) ?
C10 C11 . 1.459(17) ?
C11 H11C . 0.92(2) ?
C11 H11D . 0.91(2) ?
C12 C13 . 1.469(17) ?
C13 H13C . 0.91(2) ?
C13 H13D . 0.91(2) ?
Cu3 O13 . 1.993(8) ?
Cu3 N6 . 2.015(9) ?
Cu3 O8 . 2.096(6) ?
Cu3 O7 . 2.141(6) ?
Cl2 O10 . 1.060(19) ?
Cl2 O9 . 1.18(2) ?
Cl2 C9 . 1.697(9) ?
N2 O10 . 1.229(17) ?
N2 O9 . 1.248(18) ?
N2 C9 . 1.446(16) ?
N6 C14 . 1.134(13) ?
O7 C7 . 1.262(10) ?
O8 C8 . 1.248(10) ?
O13 H13A . 0.94(2) ?
C8 C9 . 1.413(11) ?
C8 C7 . 1.538(11) ?
C14 C15 . 1.476(17) ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 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
O12 Cu1 N5 176.8(4) . . ?
O12 Cu1 O1 89.35(19) . . ?
N5 Cu1 O1 88.9(2) . . ?
O12 Cu1 O2 91.6(2) . . ?
N5 Cu1 O2 90.7(3) . . ?
O1 Cu1 O2 76.8(2) . . ?
O11 Cu2 N4 175.7(4) . . ?
O11 Cu2 O3 89.6(2) . . ?
N4 Cu2 O3 88.2(2) . . ?
O11 Cu2 O4 91.6(2) . . ?
N4 Cu2 O4 91.4(3) . . ?
O3 Cu2 O4 75.7(2) . . ?
O5A Cl1B O6A 136.1(13) . . ?
O5A Cl1B C3 114.2(10) . . ?
O6A Cl1B C3 109.6(11) . . ?
O5B Cl1A O6B 135.4(13) . . ?
O5B Cl1A C6 116.0(13) . . ?
O6B Cl1A C6 108.5(13) . . ?
O5A N1A O6A 115.6(17) . . ?
O5A N1A C3 124(2) . . ?
O6A N1A C3 120(2) . . ?
O5B N1B O6B 116(2) . . ?
O5B N1B C6 125(4) . . ?
O6B N1B C6 119(4) . . ?
C1 O1 Cu1 116.8(6) . . ?
C2 O2 Cu1 114.6(6) . . ?
C4 O3 Cu2 115.7(6) . . ?
C5 O4 Cu2 115.1(6) . . ?
Cl1B O5A N1A 10.4(13) . . ?
Cl1A O5B N1B 9(2) . . ?
Cl1B O6A N1A 10.2(12) . . ?
Cl1A O6B N1B 9.8(18) . . ?
Cu2 O11 H11A 110(3) . . ?
Cu1 O12 H12B 114(2) . . ?
C10 N4 Cu2 174.2(10) . . ?
C12 N5 Cu1 178.0(11) . . ?
O1 C1 C6 124.0(8) . . ?
O1 C1 C2 114.2(7) . . ?
C6 C1 C2 121.7(8) . . ?
O2 C2 C3 125.0(9) . . ?
O2 C2 C1 116.9(8) . . ?
C3 C2 C1 118.1(7) . . ?
C2 C3 C4 119.9(8) . . ?
C2 C3 N1A 119.8(15) . . ?
C4 C3 N1A 120.3(15) . . ?
C2 C3 Cl1B 119.2(7) . . ?
C4 C3 Cl1B 121.0(7) . . ?
N1A C3 Cl1B 1.5(13) . . ?
O3 C4 C3 122.0(9) . . ?
O3 C4 C5 117.1(9) . . ?
C3 C4 C5 120.8(8) . . ?
O4 C5 C6 124.5(9) . . ?
O4 C5 C4 115.7(8) . . ?
C6 C5 C4 119.7(8) . . ?
C1 C6 C5 119.7(8) . . ?
C1 C6 N1B 121(3) . . ?
C5 C6 N1B 119(3) . . ?
C1 C6 Cl1A 121.8(9) . . ?
C5 C6 Cl1A 118.4(9) . . ?
N1B C6 Cl1A 0(3) . . ?
N4 C10 C11 176.5(12) . . ?
C10 C11 H11C 109(4) . . ?
C10 C11 H11D 114(4) . . ?
H11C C11 H11D 102(4) . . ?
N5 C12 C13 179.5(15) . . ?
C12 C13 H13C 111(4) . . ?
C12 C13 H13D 113(4) . . ?
H13C C13 H13D 105(4) . . ?
O13 Cu3 N6 175.4(4) . . ?
O13 Cu3 O8 89.2(2) . . ?
N6 Cu3 O8 88.4(2) . . ?
O13 Cu3 O7 91.9(2) . . ?
N6 Cu3 O7 91.3(2) . . ?
O8 Cu3 O7 76.4(2) . . ?
O10 Cl2 O9 134.3(12) . . ?
O10 Cl2 C9 114.3(10) . . ?
O9 Cl2 C9 111.0(9) . . ?
O10 N2 O9 113.1(17) . . ?
O10 N2 C9 122.0(18) . . ?
O9 N2 C9 124.8(18) . . ?
C14 N6 Cu3 175.7(10) . . ?
C7 O7 Cu3 115.4(6) . . ?
C8 O8 Cu3 116.7(6) . . ?
Cl2 O9 N2 11.8(10) . . ?
Cl2 O10 N2 9.8(10) . . ?
Cu3 O13 H13A 122(4) . . ?
O8 C8 C9 124.9(8) . . ?
O8 C8 C7 116.2(8) . . ?
C9 C8 C7 118.9(7) . . ?
O7 C7 C8 114.9(8) . . ?
C8 C9 N2 117.4(12) . . ?
C8 C9 Cl2 119.6(7) . . ?
N2 C9 Cl2 2.2(11) . . ?
N6 C14 C15 176.8(14) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O6A Cl1B O5A N1A -174(10) . . . . ?
C3 Cl1B O5A N1A 10(8) . . . . ?
O6A N1A O5A Cl1B 4(7) . . . . ?
C3 N1A O5A Cl1B -167(11) . . . . ?
O6B Cl1A O5B N1B 18E1(2) . . . . ?
C6 Cl1A O5B N1B 0E1(2) . . . . ?
O6B N1B O5B Cl1A -4(16) . . . . ?
C6 N1B O5B Cl1A -18E1(3) . . . . ?
O5A Cl1B O6A N1A 174(9) . . . . ?
C3 Cl1B O6A N1A -10(8) . . . . ?
O5A N1A O6A Cl1B -4(6) . . . . ?
C3 N1A O6A Cl1B 168(10) . . . . ?
O5B Cl1A O6B N1B -18E1(2) . . . . ?
C6 Cl1A O6B N1B 0(18) . . . . ?
O5B N1B O6B Cl1A 3(14) . . . . ?
C6 N1B O6B Cl1A 18E1(2) . . . . ?
Cu1 O1 C1 C6 173.8(6) . . . . ?
Cu1 O1 C1 C2 -7.4(8) . . . . ?
Cu1 O2 C2 C3 -176.4(6) . . . . ?
Cu1 O2 C2 C1 3.3(8) . . . . ?
O1 C1 C2 O2 2.6(10) . . . . ?
C6 C1 C2 O2 -178.5(8) . . . . ?
O1 C1 C2 C3 -177.6(7) . . . . ?
C6 C1 C2 C3 1.2(10) . . . . ?
O2 C2 C3 C4 179.5(7) . . . . ?
C1 C2 C3 C4 -0.3(11) . . . . ?
O2 C2 C3 N1A 1.5(16) . . . . ?
C1 C2 C3 N1A -178.3(13) . . . . ?
O2 C2 C3 Cl1B 0.0(11) . . . . ?
C1 C2 C3 Cl1B -179.8(6) . . . . ?
O5A N1A C3 C2 15(3) . . . . ?
O6A N1A C3 C2 -156(2) . . . . ?
O5A N1A C3 C4 -163(2) . . . . ?
O6A N1A C3 C4 26(3) . . . . ?
O5A N1A C3 Cl1B 8E1(6) . . . . ?
O6A N1A C3 Cl1B -9E1(6) . . . . ?
O5A Cl1B C3 C2 18.5(14) . . . . ?
O6A Cl1B C3 C2 -158.5(13) . . . . ?
O5A Cl1B C3 C4 -161.0(13) . . . . ?
O6A Cl1B C3 C4 22.0(15) . . . . ?
O5A Cl1B C3 N1A -10E1(6) . . . . ?
O6A Cl1B C3 N1A 9E1(6) . . . . ?
Cu2 O3 C4 C3 -175.0(6) . . . . ?
Cu2 O3 C4 C5 6.6(10) . . . . ?
C2 C3 C4 O3 -177.4(7) . . . . ?
N1A C3 C4 O3 0.6(17) . . . . ?
Cl1B C3 C4 O3 2.1(13) . . . . ?
C2 C3 C4 C5 1.0(12) . . . . ?
N1A C3 C4 C5 179.0(13) . . . . ?
Cl1B C3 C4 C5 -179.5(6) . . . . ?
Cu2 O4 C5 C6 178.4(6) . . . . ?
Cu2 O4 C5 C4 -5.0(9) . . . . ?
O3 C4 C5 O4 -1.0(11) . . . . ?
C3 C4 C5 O4 -179.5(8) . . . . ?
O3 C4 C5 C6 175.8(8) . . . . ?
C3 C4 C5 C6 -2.6(11) . . . . ?
O1 C1 C6 C5 175.9(7) . . . . ?
C2 C1 C6 C5 -2.9(11) . . . . ?
O1 C1 C6 N1B -1(3) . . . . ?
C2 C1 C6 N1B -180(3) . . . . ?
O1 C1 C6 Cl1A -0.6(13) . . . . ?
C2 C1 C6 Cl1A -179.4(8) . . . . ?
O4 C5 C6 C1 -180.0(8) . . . . ?
C4 C5 C6 C1 3.5(11) . . . . ?
O4 C5 C6 N1B -3(3) . . . . ?
C4 C5 C6 N1B -180(2) . . . . ?
O4 C5 C6 Cl1A -3.3(13) . . . . ?
C4 C5 C6 Cl1A -179.9(8) . . . . ?
O5B N1B C6 C1 157(4) . . . . ?
O6B N1B C6 C1 -19(6) . . . . ?
O5B N1B C6 C5 -19(6) . . . . ?
O6B N1B C6 C5 165(3) . . . . ?
O5B N1B C6 Cl1A 1E1(10) . . . . ?
O6B N1B C6 Cl1A -17E1(10) . . . . ?
O5B Cl1A C6 C1 157.3(13) . . . . ?
O6B Cl1A C6 C1 -18.8(17) . . . . ?
O5B Cl1A C6 C5 -19.2(16) . . . . ?
O6B Cl1A C6 C5 164.7(14) . . . . ?
O5B Cl1A C6 N1B -17E1(10) . . . . ?
O6B Cl1A C6 N1B 1E1(10) . . . . ?
O10 Cl2 O9 N2 169(4) . . . . ?
C9 Cl2 O9 N2 -3(3) . . . . ?
O10 N2 O9 Cl2 -7(3) . . . . ?
C9 N2 O9 Cl2 176(5) . . . . ?
O9 Cl2 O10 N2 -167(6) . . . . ?
C9 Cl2 O10 N2 5(5) . . . . ?
O9 N2 O10 Cl2 10(5) . . . . ?
C9 N2 O10 Cl2 -174(6) . . . . ?
Cu3 O8 C8 C9 -173.4(6) . . . . ?
Cu3 O8 C8 C7 5.7(8) . . . . ?
Cu3 O7 C7 C8 -3.8(8) . . . . ?
O8 C8 C7 O7 -1.2(9) . . . . ?
C9 C8 C7 O7 177.9(7) . . . . ?
O8 C8 C9 N2 -0.6(12) . . . . ?
C7 C8 C9 N2 -179.7(7) . . . . ?
O8 C8 C9 Cl2 -0.9(11) . . . . ?
C7 C8 C9 Cl2 -179.9(5) . . . . ?
O10 N2 C9 C8 -156.3(14) . . . . ?
O9 N2 C9 C8 20.0(19) . . . . ?
O10 N2 C9 Cl2 18(12) . . . . ?
O9 N2 C9 Cl2 -165(15) . . . . ?
O10 Cl2 C9 C8 -154.7(12) . . . . ?
O9 Cl2 C9 C8 19.0(13) . . . . ?
O10 Cl2 C9 N2 -160(14) . . . . ?
O9 Cl2 C9 N2 14(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
_geom_hbond_publ_flag
O11 H11A O2 0.94(2) 1.89(3) 2.793(9) 160(4) 3 yes
O11 H11A O5A 0.94(2) 2.33(7) 2.852(18) 115(6) 3 yes
O12 H12B O7 0.95(2) 1.90(3) 2.802(8) 157(5) 3_666 yes
C11 H11C O12 0.92(2) 2.35(3) 3.252(15) 165(5) 3_556 yes
C13 H13C O13 0.91(2) 2.38(3) 3.268(16) 162(5) 3_665 yes
C15 H15A O6B 0.96 2.86 3.36(2) 113.1 2_656 yes
C15 H15C O4 0.96 2.87 3.305(14) 108.6 1_566 yes
C15 H15B O11 0.96 2.35 3.228(19) 152.4 1_566 yes
O13 H13A O4 0.94(2) 1.98(9) 2.791(9) 143(13) 1_565 yes



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_s286
_database_code_depnum_ccdc_archive 'CCDC 2048082'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2020-12-03 deposited with the CCDC.	2021-02-25 downloaded from the CCDC.
;

_audit_creation_date             2020-01-15T10:58:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum            'C20 H14 Cl Co N3 O7'
_chemical_formula_moiety         'C18 H8 Cl Co N3 O6, C2 H6 O'
_chemical_formula_weight         502.72

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+z

_cell_length_a                   12.6659(9)
_cell_length_b                   23.6238(11)
_cell_length_c                   8.1564(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.266(6)
_cell_angle_gamma                90
_cell_volume                     2384.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1081
_cell_measurement_theta_min      6.207
_cell_measurement_theta_max      67.295
_cell_measurement_temperature    293(2)
_exptl_crystal_description       needle
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    7.060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.19851
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            5810
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0903
_diffrn_reflns_theta_min         3.742
_diffrn_reflns_theta_max         76.631
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   mixed

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             2464
_reflns_number_gt                1166
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1647
_refine_ls_R_factor_gt           0.1128
_refine_ls_wR_factor_ref         0.37
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.054
_refine_ls_number_reflns         2464
_refine_ls_number_parameters     151
_refine_ls_number_restraints     13
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.777
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0021(6)
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 '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'
Na Na 0.1353 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Co1 0.5 0.66221(6) 0.25 0.1127(10) Uani d 1 . . Co
Cl1 0.7743(11) 0.8153(5) 0.1718(9) 0.221(4) Uani d 0.5 . . Cl
O1 0.6091(7) 0.7250(2) 0.2149(6) 0.138(3) Uani d 1 . . O
O2 0.9032(6) 0.8291(2) 0.5118(7) 0.125(2) Uani d 1 . . O
O3 0.696(2) 0.8105(12) 0.080(2) 0.249(10) Uani d 0.5 . . O
O4 0.858(2) 0.8176(13) 0.175(3) 0.249(10) Uani d 0.5 . . O
N1 0.771(2) 0.8077(10) 0.189(3) 0.221(4) Uani d 0.5 . . N
N2 0.4078(7) 0.5951(3) 0.3020(8) 0.1062(19) Uani d 1 . . N
C1 0.6765(10) 0.7392(3) 0.3434(8) 0.124(3) Uani d 1 . . C
C2 0.7536(11) 0.7799(3) 0.3490(9) 0.140(4) Uani d 1 . . C
C3 0.8288(10) 0.7927(3) 0.4977(9) 0.123(3) Uani d 1 . . C
C4 0.3150(13) 0.5949(7) 0.3552(13) 0.154(5) Uani d 1 . . C
H4 0.282453 0.629265 0.369985 0.185 Uiso calc 1 . . H
C5 0.2639(19) 0.5436(13) 0.3901(19) 0.224(11) Uani d 1 . . C
H5 0.200539 0.545012 0.430418 0.269 Uiso calc 1 . . H
C6 0.3068(19) 0.4939(10) 0.3650(18) 0.192(9) Uani d 1 . . C
H6 0.2723 0.460594 0.38465 0.23 Uiso calc 1 . . H
C7 0.4010(13) 0.4915(4) 0.3108(12) 0.141(4) Uani d 1 . . C
C8 0.4510(8) 0.5435(3) 0.2768(9) 0.108(3) Uani d 1 . . C
C9 0.4531(14) 0.4412(4) 0.277(2) 0.191(11) Uani d 1 . . C
H9 0.421708 0.40661 0.293632 0.229 Uiso calc 1 . . H
C11 -0.049(5) 0.597(2) 0.560(10) 0.40(3) Uiso d 0.5 . . C
H11A -0.099776 0.567146 0.552787 0.603 Uiso calc 0.5 . . H
H11B 0.01594 0.58364 0.5291 0.603 Uiso calc 0.5 . . H
H11C -0.031202 0.611839 0.672147 0.603 Uiso calc 0.5 . . H
C10 -0.096(5) 0.644(3) 0.443(13) 0.57(5) Uiso d 0.5 . . C
H10A -0.114477 0.62888 0.329145 0.688 Uiso calc 0.5 . . H
H10B -0.161698 0.657125 0.472429 0.688 Uiso calc 0.5 . . H
O5 -0.020(3) 0.6900(19) 0.450(6) 0.335(18) Uiso d 0.5 . . O
H5A 0.037961 0.67802 0.435625 0.502 Uiso d 0.5 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Co1 N2 . 2.065(8) ?
Co1 N2 2_655 2.065(8) ?
Co1 O1 . 2.088(6) ?
Co1 O1 2_655 2.088(6) ?
Cl1 O4 . 1.05(3) ?
Cl1 O3 . 1.11(3) ?
Cl1 C2 . 1.736(10) ?
O1 C1 . 1.249(10) ?
O2 C3 . 1.264(11) ?
O3 N1 . 1.149(18) ?
O4 N1 . 1.157(18) ?
N1 C2 . 1.516(17) ?
N2 C4 . 1.337(16) ?
N2 C8 . 1.370(10) ?
C1 C2 . 1.364(14) ?
C1 C3 7_666 1.513(9) ?
C2 C3 . 1.407(12) ?
C4 C5 . 1.43(2) ?
C4 H4 . 0.93 ?
C5 C6 . 1.33(3) ?
C5 H5 . 0.93 ?
C6 C7 . 1.36(2) ?
C6 H6 . 0.93 ?
C7 C9 . 1.416(17) ?
C7 C8 . 1.436(12) ?
C8 C8 2_655 1.400(19) ?
C9 C9 2_655 1.35(3) ?
C9 H9 . 0.93 ?
C11 C10 . 1.486(14) ?
C11 H11A . 0.96 ?
C11 H11B . 0.96 ?
C11 H11C . 0.96 ?
C10 O5 . 1.453(15) ?
C10 H10A . 0.97 ?
C10 H10B . 0.97 ?
O5 H5A . 0.82(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Co1 N2 79.8(5) . 2_655 ?
N2 Co1 O2 97.5(2) . 7_666 ?
N2 Co1 O1 173.1(3) . . ?
N2 Co1 O1 95.6(3) 2_655 . ?
N2 Co1 O1 95.6(3) . 2_655 ?
N2 Co1 O1 173.1(3) 2_655 2_655 ?
O2 Co1 O1 94.5(2) 7_666 2_655 ?
O1 Co1 O1 89.4(5) . 2_655 ?
O4 Cl1 O3 140(2) . . ?
O4 Cl1 C2 109.4(15) . . ?
O3 Cl1 C2 104.0(12) . . ?
C1 O1 Co1 115.5(5) . . ?
C3 O2 Co1 115.7(5) . 7_666 ?
Cl1 O3 N1 11.9(11) . . ?
Cl1 O4 N1 11.1(13) . . ?
O3 N1 O4 124(2) . . ?
O3 N1 C2 116.6(19) . . ?
O4 N1 C2 119(2) . . ?
C4 N2 C8 116.9(9) . . ?
C4 N2 Co1 130.1(9) . . ?
C8 N2 Co1 113.0(7) . . ?
O1 C1 C2 125.0(7) . . ?
O1 C1 C3 116.0(8) . 7_666 ?
C2 C1 C3 118.9(7) . 7_666 ?
C1 C2 C3 121.9(7) . . ?
C1 C2 N1 120.5(12) . . ?
C3 C2 N1 117.1(13) . . ?
C1 C2 Cl1 123.0(7) . . ?
C3 C2 Cl1 114.9(8) . . ?
N1 C2 Cl1 3.2(13) . . ?
O2 C3 C2 125.5(7) . . ?
O2 C3 C1 115.4(7) . 7_666 ?
C2 C3 C1 119.2(8) . 7_666 ?
N2 C4 C5 122.3(16) . . ?
N2 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C6 C5 C4 120(2) . . ?
C6 C5 H5 120 . . ?
C4 C5 H5 120 . . ?
C5 C6 C7 120.2(18) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C9 125.1(15) . . ?
C6 C7 C8 118.8(14) . . ?
C9 C7 C8 116.0(13) . . ?
N2 C8 C8 117.1(5) . 2_655 ?
N2 C8 C7 121.7(10) . . ?
C8 C8 C7 121.1(8) 2_655 . ?
C9 C9 C7 122.8(8) 2_655 . ?
C9 C9 H9 118.6 2_655 . ?
C7 C9 H9 118.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C10 C11 111(3) . . ?
O5 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
O5 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C10 O5 H5A 110(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
O4 Cl1 O3 N1 128(13) . . . . ?
C2 Cl1 O3 N1 -18(9) . . . . ?
O3 Cl1 O4 N1 -123(13) . . . . ?
C2 Cl1 O4 N1 22(9) . . . . ?
Cl1 O3 N1 O4 -34(9) . . . . ?
Cl1 O3 N1 C2 157(11) . . . . ?
Cl1 O4 N1 O3 39(9) . . . . ?
Cl1 O4 N1 C2 -152(11) . . . . ?
Co1 O1 C1 C2 -178.9(10) . . . . ?
Co1 O1 C1 C3 2.2(13) . . . 7_666 ?
O1 C1 C2 C3 -178.3(11) . . . . ?
C3 C1 C2 C3 1(2) 7_666 . . . ?
O1 C1 C2 N1 -7(2) . . . . ?
C3 C1 C2 N1 172.4(15) 7_666 . . . ?
O1 C1 C2 Cl1 -4(2) . . . . ?
C3 C1 C2 Cl1 174.7(10) 7_666 . . . ?
O3 N1 C2 C1 29(3) . . . . ?
O4 N1 C2 C1 -141(2) . . . . ?
O3 N1 C2 C3 -159(2) . . . . ?
O4 N1 C2 C3 31(3) . . . . ?
O3 N1 C2 Cl1 -11E1(3) . . . . ?
O4 N1 C2 Cl1 8E1(2) . . . . ?
O4 Cl1 C2 C1 -136(2) . . . . ?
O3 Cl1 C2 C1 22(3) . . . . ?
O4 Cl1 C2 C3 39(3) . . . . ?
O3 Cl1 C2 C3 -163(2) . . . . ?
O4 Cl1 C2 N1 -10E1(3) . . . . ?
O3 Cl1 C2 N1 6E1(2) . . . . ?
Co1 O2 C3 C2 179.7(9) 7_666 . . . ?
Co1 O2 C3 C1 -0.8(12) 7_666 . . 7_666 ?
C1 C2 C3 O2 178.9(11) . . . . ?
N1 C2 C3 O2 7(2) . . . . ?
Cl1 C2 C3 O2 4.3(17) . . . . ?
C1 C2 C3 C1 -1(2) . . . 7_666 ?
N1 C2 C3 C1 -172.7(15) . . . 7_666 ?
Cl1 C2 C3 C1 -175.2(10) . . . 7_666 ?
C8 N2 C4 C5 2.1(14) . . . . ?
Co1 N2 C4 C5 -177.9(9) . . . . ?
N2 C4 C5 C6 -2(2) . . . . ?
C4 C5 C6 C7 2(3) . . . . ?
C5 C6 C7 C9 -178.9(15) . . . . ?
C5 C6 C7 C8 -2(2) . . . . ?
C4 N2 C8 C8 -179.2(8) . . . 2_655 ?
Co1 N2 C8 C8 0.8(10) . . . 2_655 ?
C4 N2 C8 C7 -2.0(12) . . . . ?
Co1 N2 C8 C7 178.0(6) . . . . ?
C6 C7 C8 N2 1.9(14) . . . . ?
C9 C7 C8 N2 179.3(10) . . . . ?
C6 C7 C8 C8 178.9(11) . . . 2_655 ?
C9 C7 C8 C8 -3.7(15) . . . 2_655 ?
C6 C7 C9 C9 180(2) . . . 2_655 ?
C8 C7 C9 C9 2(3) . . . 2_655 ?





# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_s349
_database_code_depnum_ccdc_archive 'CCDC 2048077'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2020-12-03 deposited with the CCDC.	2021-02-25 downloaded from the CCDC.
;

_audit_creation_date             2019-11-08T15:27:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum            'C32 H21 Cl Cu N5 O7'
_chemical_formula_moiety         'C30 H16 Cl Cu N5 O6, C2 H5 O'
_chemical_formula_weight         686.54

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
# CIF equivalent positions for : C2/c
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+z

_cell_length_a                   12.43260(10)
_cell_length_b                   15.87870(10)
_cell_length_c                   16.36220(10)
_cell_angle_alpha                90
_cell_angle_beta                 111.6420(10)
_cell_angle_gamma                90
_cell_volume                     3002.42(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11664
_cell_measurement_theta_min      3.978
_cell_measurement_theta_max      76.091
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_F_000             1400
_exptl_absorpt_coefficient_mu    2.344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.71553
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            14268
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_theta_min         4.733
_diffrn_reflns_theta_max         76.372
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   mixed

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             3116
_reflns_number_gt                3040
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1438
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.126
_refine_ls_number_reflns         3116
_refine_ls_number_parameters     229
_refine_ls_number_restraints     39
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0949P)²+1.6644P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.738
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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'
Br Br -0.6763 1.2805 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cu1 0.5 0.32273(2) 0.25 0.05022(18) Uani d 1 . . Cu
Cl1 0.76494(13) 0.5770(2) 0.37514(18) 0.0782(4) Uani d 0.5 . . Cl
O1 0.60759(16) 0.43134(10) 0.30817(11) 0.0656(4) Uani d 1 . . O
O2 0.61445(19) 0.72600(11) 0.29571(14) 0.0805(5) Uani d 1 . . O
O3 0.8106(6) 0.6058(8) 0.3411(6) 0.204(4) Uani d 0.5 . . O
O4 0.7690(5) 0.5535(5) 0.4359(4) 0.1234(19) Uani d 0.5 . . O
O5 0.5835(5) 0.8931(4) 0.2605(5) 0.135(2) Uani d 0.5 . . O
H5O 0.582(5) 0.8387(11) 0.266(4) 0.162 Uiso d 1 . . H
N1 0.7366(7) 0.5813(9) 0.3625(8) 0.0782(4) Uani d 0.5 . . N
N2 0.61976(16) 0.23354(12) 0.33538(12) 0.0584(4) Uani d 1 . . N
N3 0.43893(16) 0.31689(11) 0.34735(12) 0.0536(4) Uani d 1 . . N
C1 0.56333(18) 0.50192(13) 0.28236(13) 0.0536(4) Uani d 1 . . C
C2 0.5655(2) 0.65743(14) 0.27782(14) 0.0575(5) Uani d 1 . . C
C3 0.61939(19) 0.57863(14) 0.30585(14) 0.0576(5) Uani d 1 . . C
C4 0.7098(2) 0.19321(18) 0.3289(2) 0.0718(6) Uani d 1 . . C
H4 0.729691 0.203598 0.280302 0.086 Uiso calc 1 . . H
C5 0.7757(3) 0.1357(2) 0.3922(2) 0.0855(8) Uani d 1 . . C
H5 0.838193 0.108614 0.38547 0.103 Uiso calc 1 . . H
C6 0.7481(3) 0.11959(19) 0.4636(2) 0.0827(8) Uani d 1 . . C
H6 0.792049 0.08159 0.506042 0.099 Uiso calc 1 . . H
C7 0.6530(2) 0.16042(17) 0.47340(17) 0.0699(6) Uani d 1 . . C
C8 0.6178(3) 0.1488(2) 0.54642(18) 0.0826(8) Uani d 1 . . C
H8 0.657454 0.110531 0.590226 0.099 Uiso calc 1 . . H
C9 0.5284(3) 0.1922(2) 0.55299(18) 0.0803(8) Uani d 1 . . C
H9 0.507387 0.183486 0.601315 0.096 Uiso calc 1 . . H
C10 0.4651(2) 0.25155(16) 0.48698(14) 0.0637(5) Uani d 1 . . C
C11 0.3732(2) 0.29961(19) 0.49128(16) 0.0717(6) Uani d 1 . . C
H11 0.351002 0.294624 0.539454 0.086 Uiso calc 1 . . H
C12 0.3162(2) 0.3539(2) 0.42478(17) 0.0743(7) Uani d 1 . . C
H12 0.254988 0.386089 0.427237 0.089 Uiso calc 1 . . H
C13 0.3508(2) 0.36041(17) 0.35305(16) 0.0653(5) Uani d 1 . . C
H13 0.310451 0.396702 0.307399 0.078 Uiso calc 1 . . H
C14 0.49602(18) 0.26295(13) 0.41347(13) 0.0539(4) Uani d 1 . . C
C15 0.59190(19) 0.21742(13) 0.40667(14) 0.0566(5) Uani d 1 . . C
C16 0.5 0.9410(4) 0.25 0.159(3) Uani d 1 . . C
C17 0.5 1.0237(6) 0.25 0.263(8) Uani d 1 . . C
H17A 0.423484 1.043846 0.240368 0.394 Uiso calc 0.5 . . H
H17B 0.552739 1.043846 0.305675 0.394 Uiso calc 0.5 . . H
H17C 0.523777 1.043846 0.203957 0.394 Uiso calc 0.5 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 N3 2_655 2.0035(18) ?
Cu1 N3 . 2.0035(18) ?
Cu1 N2 2_655 2.1540(19) ?
Cu1 N2 . 2.1540(19) ?
Cu1 O1 2_655 2.1749(18) ?
Cu1 O1 . 2.1749(18) ?
Cl1 O3 . 1.037(9) ?
Cl1 O4 . 1.046(7) ?
Cl1 C3 . 1.746(3) ?
O1 C1 . 1.251(3) ?
O2 C2 . 1.229(3) ?
O3 N1 . 1.166(11) ?
O4 N1 . 1.202(11) ?
O5 C16 . 1.247(7) ?
O5 H5O . 0.869(16) ?
N1 C3 . 1.410(8) ?
N2 C4 . 1.327(3) ?
N2 C15 . 1.358(3) ?
N3 C13 . 1.328(3) ?
N3 C14 . 1.357(3) ?
C1 C3 . 1.385(3) ?
C1 C1 2_655 1.540(4) ?
C2 C3 . 1.414(3) ?
C2 C2 2_655 1.545(5) ?
C4 C5 . 1.397(4) ?
C4 H4 . 0.93 ?
C5 C6 . 1.358(5) ?
C5 H5 . 0.93 ?
C6 C7 . 1.409(4) ?
C6 H6 . 0.93 ?
C7 C15 . 1.406(3) ?
C7 C8 . 1.427(4) ?
C8 C9 . 1.346(5) ?
C8 H8 . 0.93 ?
C9 C10 . 1.431(4) ?
C9 H9 . 0.93 ?
C10 C11 . 1.396(4) ?
C10 C14 . 1.403(3) ?
C11 C12 . 1.364(4) ?
C11 H11 . 0.93 ?
C12 C13 . 1.395(3) ?
C12 H12 . 0.93 ?
C13 H13 . 0.93 ?
C14 C15 . 1.433(3) ?
C16 C17 . 1.313(10) ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
C17 H17A 2_655 0.96 ?
C17 H17B 2_655 0.96 ?
C17 H17C 2_655 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
N3 Cu1 N3 174.69(10) 2_655 . ?
N3 Cu1 N2 80.09(7) 2_655 2_655 ?
N3 Cu1 N2 96.38(7) . 2_655 ?
N3 Cu1 N2 96.38(7) 2_655 . ?
N3 Cu1 N2 80.09(7) . . ?
N2 Cu1 N2 97.79(10) 2_655 . ?
N3 Cu1 O1 92.35(7) 2_655 2_655 ?
N3 Cu1 O1 91.85(7) . 2_655 ?
N2 Cu1 O1 94.07(7) 2_655 2_655 ?
N2 Cu1 O1 166.31(7) . 2_655 ?
N3 Cu1 O1 91.85(7) 2_655 . ?
N3 Cu1 O1 92.35(7) . . ?
N2 Cu1 O1 166.31(7) 2_655 . ?
N2 Cu1 O1 94.07(7) . . ?
O1 Cu1 O1 75.08(9) 2_655 . ?
O3 Cl1 O4 145.5(5) . . ?
O3 Cl1 C3 106.6(4) . . ?
O4 Cl1 C3 107.3(4) . . ?
C1 O1 Cu1 116.08(15) . . ?
Cl1 O3 N1 16.6(5) . . ?
Cl1 O4 N1 15.7(5) . . ?
C16 O5 H5O 125(4) . . ?
O3 N1 O4 114.4(8) . . ?
O3 N1 C3 123.5(9) . . ?
O4 N1 C3 122.0(9) . . ?
C4 N2 C15 117.9(2) . . ?
C4 N2 Cu1 131.81(17) . . ?
C15 N2 Cu1 110.29(14) . . ?
C13 N3 C14 118.36(19) . . ?
C13 N3 Cu1 126.62(16) . . ?
C14 N3 Cu1 115.02(14) . . ?
O1 C1 C3 125.5(2) . . ?
O1 C1 C1 116.29(13) . 2_655 ?
C3 C1 C1 118.23(13) . 2_655 ?
O2 C2 C3 124.9(2) . . ?
O2 C2 C2 117.54(16) . 2_655 ?
C3 C2 C2 117.50(13) . 2_655 ?
C1 C3 N1 120.0(6) . . ?
C1 C3 C2 123.9(2) . . ?
N1 C3 C2 116.0(6) . . ?
C1 C3 Cl1 117.5(2) . . ?
N1 C3 Cl1 2.6(7) . . ?
C2 C3 Cl1 118.6(2) . . ?
N2 C4 C5 122.5(3) . . ?
N2 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C6 C5 C4 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6 120 . . ?
C7 C6 H6 120 . . ?
C15 C7 C6 116.3(2) . . ?
C15 C7 C8 119.3(3) . . ?
C6 C7 C8 124.4(2) . . ?
C9 C8 C7 121.2(2) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 121.2(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C14 117.4(2) . . ?
C11 C10 C9 123.7(2) . . ?
C14 C10 C9 118.9(2) . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120 . . ?
C10 C11 H11 120 . . ?
C11 C12 C13 119.2(2) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
N3 C13 C12 122.6(2) . . ?
N3 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
N3 C14 C10 122.5(2) . . ?
N3 C14 C15 117.51(18) . . ?
C10 C14 C15 120.0(2) . . ?
N2 C15 C7 123.6(2) . . ?
N2 C15 C14 117.04(18) . . ?
C7 C15 C14 119.4(2) . . ?
O5 C16 O5 104.7(8) . 2_655 ?
O5 C16 C17 127.7(4) . . ?
O5 C16 C17 127.7(4) 2_655 . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C17 H17A 109.471(3) . 2_655 ?
H17A C17 H17A 141.1 . 2_655 ?
H17B C17 H17A 56.3 . 2_655 ?
H17C C17 H17A 56.2 . 2_655 ?
C16 C17 H17B 109.472(2) . 2_655 ?
H17A C17 H17B 56.2 . 2_655 ?
H17B C17 H17B 141.1 . 2_655 ?
H17C C17 H17B 56.3 . 2_655 ?
H17A C17 H17B 109.5 2_655 2_655 ?
C16 C17 H17C 109.472(2) . 2_655 ?
H17A C17 H17C 56.3 . 2_655 ?
H17B C17 H17C 56.2 . 2_655 ?
H17C C17 H17C 141.1 . 2_655 ?
H17A C17 H17C 109.5 2_655 2_655 ?
H17B C17 H17C 109.5 2_655 2_655 ?

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
O4 Cl1 O3 N1 -159(4) . . . . ?
C3 Cl1 O3 N1 11(3) . . . . ?
O3 Cl1 O4 N1 158(4) . . . . ?
C3 Cl1 O4 N1 -11(3) . . . . ?
Cl1 O3 N1 O4 11(2) . . . . ?
Cl1 O3 N1 C3 -165(4) . . . . ?
Cl1 O4 N1 O3 -12(2) . . . . ?
Cl1 O4 N1 C3 164(4) . . . . ?
Cu1 O1 C1 C3 -174.97(17) . . . . ?
Cu1 O1 C1 C1 3.7(3) . . . 2_655 ?
O1 C1 C3 N1 0.9(7) . . . . ?
C1 C1 C3 N1 -177.8(6) 2_655 . . . ?
O1 C1 C3 C2 -177.7(2) . . . . ?
C1 C1 C3 C2 3.7(4) 2_655 . . . ?
O1 C1 C3 Cl1 1.6(3) . . . . ?
C1 C1 C3 Cl1 -177.0(2) 2_655 . . . ?
O3 N1 C3 C1 115.1(14) . . . . ?
O4 N1 C3 C1 -60.4(15) . . . . ?
O3 N1 C3 C2 -66.2(16) . . . . ?
O4 N1 C3 C2 118.2(12) . . . . ?
O3 N1 C3 Cl1 100(13) . . . . ?
O4 N1 C3 Cl1 -75(13) . . . . ?
O2 C2 C3 C1 -177.7(2) . . . . ?
C2 C2 C3 C1 3.7(4) 2_655 . . . ?
O2 C2 C3 N1 3.7(7) . . . . ?
C2 C2 C3 N1 -174.9(6) 2_655 . . . ?
O2 C2 C3 Cl1 3.0(3) . . . . ?
C2 C2 C3 Cl1 -175.6(2) 2_655 . . . ?
O3 Cl1 C3 C1 120.1(8) . . . . ?
O4 Cl1 C3 C1 -66.0(5) . . . . ?
O3 Cl1 C3 N1 -74(13) . . . . ?
O4 Cl1 C3 N1 100(13) . . . . ?
O3 Cl1 C3 C2 -60.6(9) . . . . ?
O4 Cl1 C3 C2 113.4(5) . . . . ?
C15 N2 C4 C5 -0.1(4) . . . . ?
Cu1 N2 C4 C5 -178.7(2) . . . . ?
N2 C4 C5 C6 0.0(5) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?
C5 C6 C7 C15 -0.5(4) . . . . ?
C5 C6 C7 C8 -179.1(3) . . . . ?
C15 C7 C8 C9 -0.9(5) . . . . ?
C6 C7 C8 C9 177.6(3) . . . . ?
C7 C8 C9 C10 0.1(5) . . . . ?
C8 C9 C10 C11 -178.6(3) . . . . ?
C8 C9 C10 C14 1.3(4) . . . . ?
C14 C10 C11 C12 1.2(4) . . . . ?
C9 C10 C11 C12 -179.0(3) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C14 N3 C13 C12 1.2(4) . . . . ?
Cu1 N3 C13 C12 -178.2(2) . . . . ?
C11 C12 C13 N3 -1.3(4) . . . . ?
C13 N3 C14 C10 0.2(3) . . . . ?
Cu1 N3 C14 C10 179.61(16) . . . . ?
C13 N3 C14 C15 -179.2(2) . . . . ?
Cu1 N3 C14 C15 0.3(2) . . . . ?
C11 C10 C14 N3 -1.3(3) . . . . ?
C9 C10 C14 N3 178.8(2) . . . . ?
C11 C10 C14 C15 178.0(2) . . . . ?
C9 C10 C14 C15 -1.9(3) . . . . ?
C4 N2 C15 C7 -0.1(3) . . . . ?
Cu1 N2 C15 C7 178.75(19) . . . . ?
C4 N2 C15 C14 178.7(2) . . . . ?
Cu1 N2 C15 C14 -2.4(2) . . . . ?
C6 C7 C15 N2 0.5(4) . . . . ?
C8 C7 C15 N2 179.1(2) . . . . ?
C6 C7 C15 C14 -178.3(2) . . . . ?
C8 C7 C15 C14 0.3(4) . . . . ?
N3 C14 C15 N2 1.6(3) . . . . ?
C10 C14 C15 N2 -177.77(19) . . . . ?
N3 C14 C15 C7 -179.5(2) . . . . ?
C10 C14 C15 C7 1.1(3) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
