# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_am_7
_database_code_depnum_ccdc_archive 'CCDC 1903317'
loop_
_audit_author_name
_audit_author_address
'Anna Dolega'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-03-14 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;

_audit_creation_date             2016-05-15T22:45:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_moiety         'C26 H22 Cu N4 O4'
_chemical_formula_sum            'C26 H22 Cu N4 O4'
_chemical_formula_weight         518.01

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

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

_cell_length_a                   6.7340(7)
_cell_length_b                   16.637(2)
_cell_length_c                   10.0554(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.871(9)
_cell_angle_gamma                90
_cell_volume                     1098.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4881
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      29.41

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

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_F_000             534
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -37 8 0.044
1 27 -6 0.037
-12 -16 6 0.115
-10 24 -3 0.102
20 -11 -2 0.168
-1 14 24 0.041
1 -14 -24 0.049
-10 6 6 0.126


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

_exptl_absorpt_coefficient_mu    1.038
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(HABITUS; Herrendorf, 1997)'
_exptl_absorpt_correction_T_min  0.8327
_exptl_absorpt_correction_T_max  0.9373

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

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_av_R_equivalents  0.0698
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_number            8175
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.103
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_full        26
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_Friedel_coverage         0
_reflns_number_total             2150
_reflns_number_gt                1759
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0712P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2150
_refine_ls_number_parameters     161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1061
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.524
_refine_diff_density_min         -1.12
_refine_diff_density_rms         0.199

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5 0.5 0.5 0.01452(16) Uani 1 2 d S T P . .
O1 O 0.4231(3) 0.40813(9) 0.59013(18) 0.0198(4) Uani 1 1 d . . . . .
O2 O 0.2009(3) 0.30918(10) 0.69470(18) 0.0253(4) Uani 1 1 d . . . . .
N2 N 1.1718(3) 0.47534(13) 0.3152(2) 0.0238(5) Uani 1 1 d . . . . .
C10 C 1.0278(3) 0.44649(13) 0.3760(2) 0.0188(5) Uani 1 1 d . . . . .
H10 H 1.0685 0.4138 0.4522 0.023 Uiso 1 1 calc R . . . .
N1 N 0.6820(3) 0.42997(11) 0.4045(2) 0.0161(4) Uani 1 1 d . . . . .
C7 C 0.6122(4) 0.21745(13) 0.4825(3) 0.0228(5) Uani 1 1 d . . . . .
H7 H 0.7011 0.1979 0.4315 0.027 Uiso 1 1 calc R . . . .
C1 C 0.6937(3) 0.35205(13) 0.4191(2) 0.0178(5) Uani 1 1 d . . . . .
H1 H 0.7847 0.3261 0.3763 0.021 Uiso 1 1 calc R . . . .
C4 C 0.3389(4) 0.27513(14) 0.6307(2) 0.0189(5) Uani 1 1 d . . . . .
C2 C 0.5843(4) 0.30190(13) 0.4925(2) 0.0177(5) Uani 1 1 d . . . . .
C9 C 0.8220(3) 0.46291(13) 0.3311(2) 0.0174(5) Uani 1 1 d . . . . .
C12 C 0.9071(4) 0.54070(15) 0.1528(3) 0.0252(5) Uani 1 1 d . . . . .
H12 H 0.8703 0.572 0.0746 0.03 Uiso 1 1 calc R . . . .
C3 C 0.4509(3) 0.33217(12) 0.5708(2) 0.0168(5) Uani 1 1 d . . . . .
C13 C 0.7592(4) 0.51235(14) 0.2187(3) 0.0215(5) Uani 1 1 d . . . . .
H13 H 0.6228 0.5262 0.1881 0.026 Uiso 1 1 calc R . . . .
C5 C 0.3712(4) 0.19360(14) 0.6215(3) 0.0223(5) Uani 1 1 d . . . . .
H5 H 0.301 0.1575 0.6648 0.027 Uiso 1 1 calc R . . . .
C11 C 1.1091(4) 0.52156(15) 0.2056(3) 0.0252(6) Uani 1 1 d . . . . .
H11 H 1.2066 0.5421 0.1623 0.03 Uiso 1 1 calc R . . . .
C8 C 0.0809(4) 0.25605(15) 0.7550(3) 0.0282(6) Uani 1 1 d . . . . .
H8A H 0.0052 0.2209 0.6863 0.042 Uiso 1 1 calc GR . . . .
H8B H -0.0117 0.2866 0.795 0.042 Uiso 1 1 calc GR . . . .
H8C H 0.1682 0.2247 0.8243 0.042 Uiso 1 1 calc GR . . . .
C6 C 0.5097(4) 0.16507(13) 0.5470(3) 0.0247(5) Uani 1 1 d . . . . .
H6 H 0.5316 0.1101 0.5415 0.03 Uiso 1 1 calc R . . . .



#----------------------------------------------------------------------------#
#                   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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9064(16) . ?
Cu1 O1 1.9065(16) 3_666 ?
Cu1 N1 2.0753(19) . ?
Cu1 N1 2.0753(19) 3_666 ?
O1 C3 1.298(3) . ?
O2 C4 1.366(3) . ?
O2 C8 1.421(3) . ?
N2 C10 1.345(3) . ?
N2 C11 1.333(4) . ?
C10 H10 0.93 . ?
C10 C9 1.386(3) . ?
N1 C1 1.305(3) . ?
N1 C9 1.430(3) . ?
C7 H7 0.93 . ?
C7 C2 1.424(3) . ?
C7 C6 1.362(4) . ?
C1 H1 0.93 . ?
C1 C2 1.423(3) . ?
C4 C3 1.426(3) . ?
C4 C5 1.380(3) . ?
C2 C3 1.413(3) . ?
C9 C13 1.386(4) . ?
C12 H12 0.93 . ?
C12 C13 1.395(3) . ?
C12 C11 1.383(4) . ?
C13 H13 0.93 . ?
C5 H5 0.93 . ?
C5 C6 1.403(4) . ?
C11 H11 0.93 . ?
C8 H8A 0.96 . ?
C8 H8B 0.96 . ?
C8 H8C 0.96 . ?
C6 H6 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
O1 Cu1 O1 180.00(16) . 3_666 ?
O1 Cu1 N1 91.19(7) 3_666 3_666 ?
O1 Cu1 N1 88.81(7) . 3_666 ?
O1 Cu1 N1 91.19(7) . . ?
O1 Cu1 N1 88.81(7) 3_666 . ?
N1 Cu1 N1 180 . 3_666 ?
C3 O1 Cu1 130.23(15) . . ?
C4 O2 C8 117.01(19) . . ?
C11 N2 C10 117.0(2) . . ?
N2 C10 H10 118.3 . . ?
N2 C10 C9 123.5(2) . . ?
C9 C10 H10 118.3 . . ?
C1 N1 Cu1 122.17(16) . . ?
C1 N1 C9 114.13(19) . . ?
C9 N1 Cu1 123.31(14) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C2 120.6(2) . . ?
N1 C1 H1 116 . . ?
N1 C1 C2 128.0(2) . . ?
C2 C1 H1 116 . . ?
O2 C4 C3 113.7(2) . . ?
O2 C4 C5 125.0(2) . . ?
C5 C4 C3 121.3(2) . . ?
C1 C2 C7 116.7(2) . . ?
C3 C2 C7 120.1(2) . . ?
C3 C2 C1 123.2(2) . . ?
C10 C9 N1 118.9(2) . . ?
C10 C9 C13 119.0(2) . . ?
C13 C9 N1 122.1(2) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C11 C12 C13 119.0(2) . . ?
O1 C3 C4 118.5(2) . . ?
O1 C3 C2 124.1(2) . . ?
C2 C3 C4 117.4(2) . . ?
C9 C13 C12 117.9(2) . . ?
C9 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.1(2) . . ?
C6 C5 H5 119.9 . . ?
N2 C11 C12 123.6(2) . . ?
N2 C11 H11 118.2 . . ?
C12 C11 H11 118.2 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?

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 C3 C4 -166.01(16) . . . . ?
Cu1 O1 C3 C2 13.3(3) . . . . ?
Cu1 N1 C1 C2 3.3(3) . . . . ?
Cu1 N1 C9 C10 118.2(2) . . . . ?
Cu1 N1 C9 C13 -60.1(3) . . . . ?
O2 C4 C3 O1 4.7(3) . . . . ?
O2 C4 C3 C2 -174.7(2) . . . . ?
O2 C4 C5 C6 176.6(2) . . . . ?
N2 C10 C9 N1 -179.2(2) . . . . ?
N2 C10 C9 C13 -0.8(4) . . . . ?
C10 N2 C11 C12 0.0(4) . . . . ?
C10 C9 C13 C12 2.5(3) . . . . ?
N1 C1 C2 C7 174.6(2) . . . . ?
N1 C1 C2 C3 -4.5(4) . . . . ?
N1 C9 C13 C12 -179.2(2) . . . . ?
C7 C2 C3 O1 177.0(2) . . . . ?
C7 C2 C3 C4 -3.7(3) . . . . ?
C1 N1 C9 C10 -54.8(3) . . . . ?
C1 N1 C9 C13 126.9(2) . . . . ?
C1 C2 C3 O1 -4.0(4) . . . . ?
C1 C2 C3 C4 175.3(2) . . . . ?
C4 C5 C6 C7 -0.4(4) . . . . ?
C2 C7 C6 C5 1.6(4) . . . . ?
C9 N1 C1 C2 176.4(2) . . . . ?
C3 C4 C5 C6 -2.9(4) . . . . ?
C13 C12 C11 N2 1.8(4) . . . . ?
C5 C4 C3 O1 -175.7(2) . . . . ?
C5 C4 C3 C2 4.9(3) . . . . ?
C11 N2 C10 C9 -0.5(4) . . . . ?
C11 C12 C13 C9 -2.9(4) . . . . ?
C8 O2 C4 C3 179.0(2) . . . . ?
C8 O2 C4 C5 -0.6(4) . . . . ?
C6 C7 C2 C1 -178.5(2) . . . . ?
C6 C7 C2 C3 0.6(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_am_14
_database_code_depnum_ccdc_archive 'CCDC 1903320'
loop_
_audit_author_name
_audit_author_address
'Anna Dolega'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-03-14 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;

_audit_creation_date             2018-09-06T22:09:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C26 H22 Cu N4 O4'
_chemical_formula_weight         518.01

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

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

_cell_length_a                   13.678(2)
_cell_length_b                   12.3462(17)
_cell_length_c                   14.989(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.006(13)
_cell_angle_gamma                90
_cell_volume                     2274.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    10529
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      29.43

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

_exptl_crystal_description       plate
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.066
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_F_000             1068
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 -14 0.052
3 2 25 0.046
-6 -2 5 0.038
22 7 -16 0.047
-2 6 1 0.025
4 21 5 0.023
4 -27 -5 0.022
22 -9 1 0.07


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

_exptl_absorpt_coefficient_mu    1.002
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
        Structure Analysis", published in
        F. R. Ahmed (Editor), "Crystallographic Computing",
        Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.9126
_exptl_absorpt_correction_T_max  0.9681

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

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_av_R_equivalents  0.0925
_diffrn_reflns_av_unetI/netI     0.087
_diffrn_reflns_number            16509
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.024
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_coverage         0
_reflns_number_total             4446
_reflns_number_gt                2784
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0509P)²+1.2224P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4446
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.093

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.23572(4) 0.93385(5) 0.97520(4) 0.01975(15) Uani 1 1 d . . . . .
O3 O -0.0236(2) 1.0598(3) 0.6887(2) 0.0299(7) Uani 1 1 d . . . . .
C1 C 0.1271(3) 0.9431(4) 1.1007(3) 0.0195(8) Uani 1 1 d . . . . .
H1 H 0.0678 0.9277 1.1134 0.023 Uiso 1 1 calc R U . . .
O1 O 0.3326(2) 1.0064(3) 1.0946(2) 0.0223(7) Uani 1 1 d . . . . .
C7 C 0.1844(4) 1.0599(4) 1.2441(3) 0.0236(9) Uani 1 1 d . . . . .
H7 H 0.1188 1.0435 1.2458 0.028 Uiso 1 1 calc R U . . .
O2 O 0.1322(2) 0.9702(3) 0.8421(2) 0.0243(7) Uani 1 1 d . . . . .
N2 N 0.3492(3) 0.9031(3) 0.9336(2) 0.0195(8) Uani 1 1 d . . . . .
C14 C 0.3501(3) 0.9397(4) 0.8521(3) 0.0198(9) Uani 1 1 d . . . . .
H14 H 0.4127 0.9286 0.8436 0.024 Uiso 1 1 calc R U . . .
N1 N 0.1286(3) 0.8966(3) 1.0229(2) 0.0204(8) Uani 1 1 d . . . . .
C9 C 0.0450(3) 0.8202(4) 0.9694(3) 0.0204(9) Uani 1 1 d . . . . .
C3 C 0.3057(3) 1.0407(3) 1.1635(3) 0.0196(9) Uani 1 1 d . . . . .
C2 C 0.2072(4) 1.0152(4) 1.1682(3) 0.0213(9) Uani 1 1 d . . . . .
N4 N -0.0430(3) 0.8180(3) 0.9864(2) 0.0245(8) Uani 1 1 d . . . . .
C4 C 0.3806(4) 1.1088(4) 1.2400(3) 0.0219(9) Uani 1 1 d . . . . .
C10 C 0.0599(4) 0.7498(4) 0.9036(3) 0.0287(11) Uani 1 1 d . . . . .
H10 H 0.1224 0.7535 0.8938 0.034 Uiso 1 1 calc R U . . .
C6 C 0.2570(4) 1.1270(4) 1.3150(3) 0.0274(10) Uani 1 1 d . . . . .
H6 H 0.2405 1.157 1.3637 0.033 Uiso 1 1 calc R U . . .
C5 C 0.3568(4) 1.1499(4) 1.3132(3) 0.0275(10) Uani 1 1 d . . . . .
H5 H 0.4075 1.1935 1.3624 0.033 Uiso 1 1 calc R U . . .
C12 C -0.1112(4) 0.6708(4) 0.8698(3) 0.0317(11) Uani 1 1 d . . . . .
H12 H -0.166 0.6205 0.8373 0.038 Uiso 1 1 calc R U . . .
C11 C -0.0195(4) 0.6749(4) 0.8537(4) 0.0325(11) Uani 1 1 d . . . . .
H11 H -0.0115 0.6272 0.8093 0.039 Uiso 1 1 calc R U . . .
C13 C -0.1186(4) 0.7449(4) 0.9365(3) 0.0270(10) Uani 1 1 d . . . . .
H13 H -0.1808 0.7431 0.9468 0.032 Uiso 1 1 calc R U . . .
O4 O 0.4757(2) 1.1287(3) 1.2323(2) 0.0260(7) Uani 1 1 d . . . . .
C8 C 0.5549(4) 1.1944(5) 1.3088(4) 0.0374(12) Uani 1 1 d . . . . .
H8A H 0.5245 1.2645 1.3087 0.056 Uiso 1 1 calc R U . . .
H8B H 0.6179 1.2023 1.2967 0.056 Uiso 1 1 calc R U . . .
H8C H 0.5754 1.1605 1.3721 0.056 Uiso 1 1 calc R U . . .
N3 N 0.4136(3) 0.7839(3) 1.0642(2) 0.0233(8) Uani 1 1 d . . . . .
C17 C 0.0757(3) 1.0565(4) 0.6875(3) 0.0251(9) Uani 1 1 d . . . . .
C23 C 0.4403(4) 0.8456(4) 1.0044(3) 0.0207(9) Uani 1 1 d . . . . .
C19 C 0.2013(4) 1.0862(4) 0.6171(3) 0.0270(11) Uani 1 1 d . . . . .
H19 H 0.2153 1.1139 0.5661 0.032 Uiso 1 1 calc R U . . .
C21 C 0.2619(3) 0.9954(4) 0.7753(3) 0.0204(9) Uani 1 1 d . . . . .
C16 C 0.1582(4) 1.0053(4) 0.7733(3) 0.0209(9) Uani 1 1 d . . . . .
C27 C 0.4949(4) 0.7287(4) 1.1351(3) 0.0282(10) Uani 1 1 d . . . . .
H27 H 0.4785 0.6856 1.1777 0.034 Uiso 1 1 calc R U . . .
C24 C 0.5436(4) 0.8526(4) 1.0105(3) 0.0246(10) Uani 1 1 d . . . . .
H24 H 0.5578 0.8946 0.966 0.029 Uiso 1 1 calc R U . . .
C18 C 0.0971(4) 1.0959(4) 0.6129(3) 0.0292(11) Uani 1 1 d . . . . .
H18 H 0.042 1.1296 0.5587 0.035 Uiso 1 1 calc R U . . .
C20 C 0.2814(4) 1.0363(4) 0.6958(3) 0.0260(11) Uani 1 1 d . . . . .
H20 H 0.35 1.0287 0.6978 0.031 Uiso 1 1 calc R U . . .
C25 C 0.6258(4) 0.7950(4) 1.0853(3) 0.0288(11) Uani 1 1 d . . . . .
H25 H 0.6969 0.7987 1.0928 0.035 Uiso 1 1 calc R U . . .
C26 C 0.6006(4) 0.7316(4) 1.1488(3) 0.0335(12) Uani 1 1 d . . . . .
H26 H 0.6543 0.6921 1.1995 0.04 Uiso 1 1 calc R U . . .
C22 C -0.1104(4) 1.1118(5) 0.6062(4) 0.0412(13) Uani 1 1 d . . . . .
H22A H -0.1157 1.0815 0.5453 0.062 Uiso 1 1 calc R U . . .
H22B H -0.0958 1.188 0.6077 0.062 Uiso 1 1 calc R U . . .
H22C H -0.1776 1.1007 0.6105 0.062 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.919(3) . ?
Cu1 O2 1.925(3) . ?
Cu1 N1 1.946(4) . ?
Cu1 N2 1.947(4) . ?
O3 C17 1.367(5) . ?
O3 C22 1.437(5) . ?
C1 N1 1.309(5) . ?
C1 C2 1.430(6) . ?
O1 C3 1.309(5) . ?
C7 C6 1.370(6) . ?
C7 C2 1.417(6) . ?
O2 C16 1.305(5) . ?
N2 C14 1.309(5) . ?
N2 C23 1.422(6) . ?
C14 C21 1.427(6) . ?
N1 C9 1.428(6) . ?
C9 N4 1.336(6) . ?
C9 C10 1.395(6) . ?
C3 C2 1.415(6) . ?
C3 C4 1.430(6) . ?
N4 C13 1.328(6) . ?
C4 C5 1.370(6) . ?
C4 O4 1.377(5) . ?
C10 C11 1.371(7) . ?
C6 C5 1.406(7) . ?
C12 C11 1.378(7) . ?
C12 C13 1.391(7) . ?
O4 C8 1.434(5) . ?
N3 C27 1.339(6) . ?
N3 C23 1.343(5) . ?
C17 C18 1.363(6) . ?
C17 C16 1.433(6) . ?
C23 C24 1.379(6) . ?
C19 C20 1.356(6) . ?
C19 C18 1.404(7) . ?
C21 C16 1.410(6) . ?
C21 C20 1.424(6) . ?
C27 C26 1.368(7) . ?
C24 C25 1.386(6) . ?
C25 C26 1.387(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 138.67(14) . . ?
O1 Cu1 N1 95.18(13) . . ?
O2 Cu1 N1 96.07(14) . . ?
O1 Cu1 N2 93.93(14) . . ?
O2 Cu1 N2 92.36(13) . . ?
N1 Cu1 N2 154.92(14) . . ?
C17 O3 C22 116.9(3) . . ?
N1 C1 C2 126.7(4) . . ?
C3 O1 Cu1 124.7(3) . . ?
C6 C7 C2 121.2(4) . . ?
C16 O2 Cu1 124.4(3) . . ?
C14 N2 C23 120.4(4) . . ?
C14 N2 Cu1 124.5(3) . . ?
C23 N2 Cu1 114.8(3) . . ?
N2 C14 C21 124.7(4) . . ?
C1 N1 C9 118.0(4) . . ?
C1 N1 Cu1 122.2(3) . . ?
C9 N1 Cu1 119.8(3) . . ?
N4 C9 C10 123.1(4) . . ?
N4 C9 N1 118.2(4) . . ?
C10 C9 N1 118.6(4) . . ?
O1 C3 C2 124.8(4) . . ?
O1 C3 C4 118.2(4) . . ?
C2 C3 C4 117.0(4) . . ?
C3 C2 C7 120.2(4) . . ?
C3 C2 C1 123.6(4) . . ?
C7 C2 C1 116.1(4) . . ?
C13 N4 C9 116.7(4) . . ?
C5 C4 O4 124.4(4) . . ?
C5 C4 C3 121.4(4) . . ?
O4 C4 C3 114.1(4) . . ?
C11 C10 C9 118.6(5) . . ?
C7 C6 C5 119.1(4) . . ?
C4 C5 C6 121.0(4) . . ?
C11 C12 C13 117.4(4) . . ?
C10 C11 C12 119.5(5) . . ?
N4 C13 C12 124.6(5) . . ?
C4 O4 C8 116.4(3) . . ?
C27 N3 C23 116.4(4) . . ?
C18 C17 O3 124.9(4) . . ?
C18 C17 C16 121.7(4) . . ?
O3 C17 C16 113.4(4) . . ?
N3 C23 C24 124.2(4) . . ?
N3 C23 N2 112.1(4) . . ?
C24 C23 N2 123.7(4) . . ?
C20 C19 C18 119.7(4) . . ?
C16 C21 C20 120.5(4) . . ?
C16 C21 C14 123.1(4) . . ?
C20 C21 C14 116.4(4) . . ?
O2 C16 C21 125.1(4) . . ?
O2 C16 C17 118.4(4) . . ?
C21 C16 C17 116.5(4) . . ?
N3 C27 C26 124.1(4) . . ?
C23 C24 C25 117.8(4) . . ?
C17 C18 C19 120.8(4) . . ?
C19 C20 C21 120.9(4) . . ?
C24 C25 C26 119.2(5) . . ?
C27 C26 C25 118.4(4) . . ?

####################################################################### 
# 
# 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_am1_2019
_database_code_depnum_ccdc_archive 'CCDC 1946386'
loop_
_audit_author_name
_audit_author_address
'Anna Dolega'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-08-09 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;

_audit_creation_date             2019-08-09T13:37:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C26 H22 Cu N4 O4'
_chemical_formula_weight         518.01

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1880(5)
_cell_length_b                   11.6234(9)
_cell_length_c                   14.5327(10)
_cell_angle_alpha                73.227(5)
_cell_angle_beta                 80.921(5)
_cell_angle_gamma                74.794(6)
_cell_volume                     1117.40(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    10540
_cell_measurement_theta_min      1.88
_cell_measurement_theta_max      29.48

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

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.102
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.063
_exptl_crystal_density_diffrn    1.54
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             534
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -2 1 0.022
-2 0 5 0.026
1 3 5 0.055
2 1 -2 0.041
0 -4 -3 0.056
1 0 3 0.066
0 2 1 0.046
-1 -1 -4 0.029


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

_exptl_absorpt_coefficient_mu    1.02
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
        Structure Analysis", published in
        F. R. Ahmed (Editor), "Crystallographic Computing",
        Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.8971
_exptl_absorpt_correction_T_max  0.9549

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

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_number            11777
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 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
_reflns_Friedel_coverage         0
_reflns_number_total             4389
_reflns_number_gt                3261
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       
;
        X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
        X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
        X-Area Integrate 1.72.0.0 (STOE, 2018)
        X-Area X-Red32 1.63.4.0 (STOE, 2017)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image
processing, for the correction and scaling of reflection intensities and
        for outlier rejection, version 1.81, Darmstadt 2018
;

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

_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1670P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4389
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0767
_refine_ls_wR_factor_ref         0.2278
_refine_ls_wR_factor_gt          0.2075
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.156
_refine_diff_density_min         -1.181
_refine_diff_density_rms         0.196

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.38138(9) 0.48637(5) 0.24003(4) 0.0300(3) Uani 1 1 d . . . . .
O1 O 0.4792(5) 0.3711(3) 0.3528(2) 0.0318(8) Uani 1 1 d . . . . .
O3 O 0.2696(5) 0.5924(3) 0.1276(2) 0.0308(8) Uani 1 1 d . . . . .
O2 O 0.5775(6) 0.1587(3) 0.4753(3) 0.0404(9) Uani 1 1 d . . . . .
N1 N 0.2865(6) 0.6237(4) 0.3214(3) 0.0293(9) Uani 1 1 d . . . . .
N3 N 0.6578(6) 0.4791(4) 0.1695(3) 0.0282(9) Uani 1 1 d . . . . .
N4 N 1.1413(6) 0.4010(4) 0.2593(3) 0.0288(9) Uani 1 1 d . . . . .
N2 N 0.0420(7) 0.9557(4) 0.2563(4) 0.0399(11) Uani 1 1 d . . . . .
C8 C 0.2495(7) 0.5915(5) 0.4143(4) 0.0318(11) Uani 1 1 d . . . . .
H8 H 0.1906 0.6541 0.4445 0.038 Uiso 1 1 calc R U . . .
C15 C 0.2250(7) 0.7418(5) -0.0214(4) 0.0301(11) Uani 1 1 d . . . . .
C1 C 0.4076(7) 0.3664(5) 0.4422(4) 0.0292(10) Uani 1 1 d . . . . .
C18 C 0.6218(7) 0.7067(5) -0.0665(4) 0.0315(11) Uani 1 1 d . . . . .
H18 H 0.7547 0.6936 -0.0826 0.031(14) Uiso 1 1 calc R . . . .
C9 C 0.2457(8) 0.7509(5) 0.2751(4) 0.0322(11) Uani 1 1 d . . . . .
C22 C 0.8269(7) 0.4077(5) 0.2176(3) 0.0292(10) Uani 1 1 d . . . . .
C16 C 0.2986(8) 0.8118(5) -0.1046(4) 0.0325(11) Uani 1 1 d . . . . .
H16 H 0.2148 0.8715 -0.1463 0.028(14) Uiso 1 1 calc R . . . .
C17 C 0.5001(8) 0.7946(5) -0.1282(4) 0.0338(11) Uani 1 1 d . . . . .
H17 H 0.5495 0.8425 -0.185 0.07(2) Uiso 1 1 calc R . . . .
C12 C 0.3368(8) 0.9214(5) 0.1546(4) 0.0357(12) Uani 1 1 d . . . . .
H12 H 0.4213 0.9541 0.1045 0.046(18) Uiso 1 1 calc R . . . .
C13 C 0.3759(8) 0.7964(5) 0.1994(4) 0.0352(12) Uani 1 1 d . . . . .
H13 H 0.4864 0.7435 0.1797 0.048(18) Uiso 1 1 calc R . . . .
C2 C 0.4567(8) 0.2512(5) 0.5127(4) 0.0343(12) Uani 1 1 d . . . . .
C14 C 0.3477(7) 0.6526(4) 0.0465(3) 0.0292(11) Uani 1 1 d . . . . .
C26 C 0.8385(7) 0.2868(5) 0.2721(3) 0.0289(10) Uani 1 1 d . . . . .
H26 H 0.7381 0.2482 0.2763 0.009(10) Uiso 1 1 calc R . . . .
C19 C 0.5498(7) 0.6354(4) 0.0212(4) 0.0289(10) Uani 1 1 d . . . . .
C6 C 0.2917(7) 0.4672(5) 0.4749(4) 0.0320(11) Uani 1 1 d . . . . .
C23 C 0.9823(7) 0.4606(4) 0.2139(3) 0.0284(10) Uani 1 1 d . . . . .
H23 H 0.9745 0.5418 0.1777 0.007(10) Uiso 1 1 calc R . . . .
C21 C 0.6913(7) 0.5465(5) 0.0826(4) 0.0303(11) Uani 1 1 d . . . . .
H21 H 0.8199 0.5364 0.0573 0.047(18) Uiso 1 1 calc R . . . .
C24 C 1.1493(7) 0.2838(5) 0.3125(4) 0.0313(11) Uani 1 1 d . . . . .
H24 H 1.2584 0.2413 0.3453 0.030(14) Uiso 1 1 calc R . . . .
C5 C 0.2268(8) 0.4513(5) 0.5753(4) 0.0363(12) Uani 1 1 d . . . . .
H5 H 0.1541 0.5188 0.5971 0.034(15) Uiso 1 1 calc R . . . .
C10 C 0.0814(8) 0.8347(5) 0.2988(4) 0.0352(12) Uani 1 1 d . . . . .
H10 H -0.0075 0.8045 0.3477 0.033(15) Uiso 1 1 calc R . . . .
C25 C 1.0026(7) 0.2246(5) 0.3202(4) 0.0328(11) Uani 1 1 d . . . . .
H25 H 1.0135 0.1436 0.3574 0.035(15) Uiso 1 1 calc R . . . .
C11 C 0.1704(8) 0.9968(5) 0.1854(4) 0.0386(12) Uani 1 1 d . . . . .
H11 H 0.1463 1.0809 0.1552 0.047(18) Uiso 1 1 calc R . . . .
C3 C 0.3875(8) 0.2376(5) 0.6082(4) 0.0383(12) Uani 1 1 d . . . . .
H3 H 0.4184 0.1612 0.6526 0.034(15) Uiso 1 1 calc R . . . .
C4 C 0.2700(8) 0.3398(5) 0.6382(4) 0.0388(13) Uani 1 1 d . . . . .
H4 H 0.2214 0.3302 0.7025 0.046(17) Uiso 1 1 calc R . . . .
C7 C 0.6620(10) 0.0480(5) 0.5430(5) 0.0506(16) Uani 1 1 d . . . . .
H7A H 0.5617 0.0094 0.5804 0.06(2) Uiso 1 1 calc R . . . .
H7B H 0.7325 0.0675 0.5852 0.087 Uiso 1 1 calc R U . . .
H7C H 0.7486 -0.0074 0.509 0.087 Uiso 1 1 calc R U . . .
O4 O 0.0257(5) 0.7512(3) -0.0042(3) 0.0341(8) Uani 1 1 d . . . . .
C20 C -0.0666(8) 0.8179(5) 0.0651(4) 0.0385(12) Uani 1 1 d . . . . .
H20A H -0.0561 0.9022 0.0409 0.058 Uiso 1 1 calc R U . . .
H20B H -0.0052 0.7815 0.1242 0.058 Uiso 1 1 calc R U . . .
H20C H -0.2007 0.815 0.0771 0.058 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O3 1.889(3) . ?
Cu1 O1 1.892(3) . ?
Cu1 N3 2.080(4) . ?
Cu1 N4 2.151(4) 1_455 ?
Cu1 N1 2.162(4) . ?
O1 C1 1.311(6) . ?
O3 C14 1.310(6) . ?
O2 C2 1.380(7) . ?
O2 C7 1.429(6) . ?
N1 C8 1.296(7) . ?
N1 C9 1.409(6) . ?
N3 C21 1.302(6) . ?
N3 C22 1.436(6) . ?
N4 C23 1.334(6) . ?
N4 C24 1.350(6) . ?
N4 Cu1 2.151(4) 1_655 ?
N2 C10 1.337(7) . ?
N2 C11 1.337(8) . ?
C8 C6 1.440(7) . ?
C15 C16 1.364(7) . ?
C15 O4 1.395(6) . ?
C15 C14 1.424(7) . ?
C1 C6 1.406(7) . ?
C1 C2 1.429(7) . ?
C18 C17 1.365(7) . ?
C18 C19 1.409(7) . ?
C9 C10 1.387(7) . ?
C9 C13 1.401(8) . ?
C22 C26 1.388(7) . ?
C22 C23 1.397(7) . ?
C16 C17 1.409(7) . ?
C12 C11 1.382(8) . ?
C12 C13 1.383(7) . ?
C2 C3 1.376(8) . ?
C14 C19 1.417(7) . ?
C26 C25 1.388(7) . ?
C19 C21 1.450(7) . ?
C6 C5 1.434(7) . ?
C24 C25 1.377(7) . ?
C5 C4 1.344(8) . ?
C3 C4 1.403(8) . ?
O4 C20 1.423(6) . ?

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 Cu1 O1 175.01(15) . . ?
O3 Cu1 N3 91.05(15) . . ?
O1 Cu1 N3 91.87(15) . . ?
O3 Cu1 N4 85.27(15) . 1_455 ?
O1 Cu1 N4 89.91(15) . 1_455 ?
N3 Cu1 N4 140.62(16) . 1_455 ?
O3 Cu1 N1 93.95(15) . . ?
O1 Cu1 N1 88.50(15) . . ?
N3 Cu1 N1 114.66(16) . . ?
N4 Cu1 N1 104.71(16) 1_455 . ?
C1 O1 Cu1 127.1(3) . . ?
C14 O3 Cu1 131.1(3) . . ?
C2 O2 C7 116.9(4) . . ?
C8 N1 C9 117.5(4) . . ?
C8 N1 Cu1 120.8(4) . . ?
C9 N1 Cu1 121.4(3) . . ?
C21 N3 C22 115.3(4) . . ?
C21 N3 Cu1 123.0(3) . . ?
C22 N3 Cu1 121.5(3) . . ?
C23 N4 C24 117.5(4) . . ?
C23 N4 Cu1 120.6(3) . 1_655 ?
C24 N4 Cu1 121.8(3) . 1_655 ?
C10 N2 C11 116.8(5) . . ?
N1 C8 C6 125.7(5) . . ?
C16 C15 O4 119.8(5) . . ?
C16 C15 C14 121.6(5) . . ?
O4 C15 C14 118.4(4) . . ?
O1 C1 C6 125.0(5) . . ?
O1 C1 C2 117.7(5) . . ?
C6 C1 C2 117.2(5) . . ?
C17 C18 C19 121.2(5) . . ?
C10 C9 C13 117.4(5) . . ?
C10 C9 N1 123.8(5) . . ?
C13 C9 N1 118.8(5) . . ?
C26 C22 C23 118.1(4) . . ?
C26 C22 N3 121.6(5) . . ?
C23 C22 N3 120.3(4) . . ?
C15 C16 C17 120.7(5) . . ?
C18 C17 C16 119.2(5) . . ?
C11 C12 C13 118.9(5) . . ?
C12 C13 C9 118.8(5) . . ?
C3 C2 O2 124.8(5) . . ?
C3 C2 C1 121.7(5) . . ?
O2 C2 C1 113.5(5) . . ?
O3 C14 C19 124.0(4) . . ?
O3 C14 C15 119.1(5) . . ?
C19 C14 C15 116.9(4) . . ?
C25 C26 C22 118.7(5) . . ?
C18 C19 C14 120.3(4) . . ?
C18 C19 C21 116.9(4) . . ?
C14 C19 C21 122.8(4) . . ?
C1 C6 C5 119.9(5) . . ?
C1 C6 C8 123.3(5) . . ?
C5 C6 C8 116.5(5) . . ?
N4 C23 C22 123.6(5) . . ?
N3 C21 C19 127.1(5) . . ?
N4 C24 C25 122.7(5) . . ?
C4 C5 C6 120.6(5) . . ?
N2 C10 C9 124.4(5) . . ?
C24 C25 C26 119.4(5) . . ?
N2 C11 C12 123.6(5) . . ?
C2 C3 C4 119.6(5) . . ?
C5 C4 C3 120.9(5) . . ?
C15 O4 C20 114.1(4) . . ?

####################################################################### 
# 
# 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_am_6_sq
_database_code_depnum_ccdc_archive 'CCDC 1903318'
loop_
_audit_author_name
_audit_author_address
'Anna Dolega'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-03-14 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;

_audit_creation_date             2016-05-15T21:12:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C26 H22 N4 O4 Zn'
_chemical_formula_weight         519.84

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
x,1/2-y,1/2+z

_cell_length_a                   11.875(8)
_cell_length_b                   10.802(8)
_cell_length_c                   20.684(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.88(5)
_cell_angle_gamma                90
_cell_volume                     2647(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    192
_cell_measurement_theta_min      3.49
_cell_measurement_theta_max      11.93

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

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.178
_exptl_crystal_size_mid          0.143
_exptl_crystal_size_min          0.096
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             1072
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-17 2 14 0.041
8 5 23 0.092
27 3 10 0.118
17 -1 -8 0.114
9 -5 -26 0.086
-14 -5 -23 0.073
-12 -1 -3 0.06
-13 2 12 0.041
0 15 -10 0.045
-4 8 -21 0.082
4 17 7 0.039
7 -3 30 0.105
-2 -16 1 0.051


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

_exptl_absorpt_coefficient_mu    0.964
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(HABITUS; Herrendorf, 1997)'
_exptl_absorpt_correction_T_min  0.8563
_exptl_absorpt_correction_T_max  0.9278

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

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_number            19707
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.528
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.999
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             5196
_reflns_number_gt                3733
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1648P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5196
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.2305
_refine_ls_wR_factor_gt          0.1719
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.763
_refine_diff_density_min         -1.302
_refine_diff_density_rms         0.195

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1192(4) 0.3927(4) 0.3581(2) 0.0304(10) Uani 1 1 d . . . . .
H1 H -0.1316 0.314 0.3744 0.036 Uiso 1 1 calc R U . . .
C2 C -0.2032(4) 0.4400(5) 0.3106(2) 0.0291(10) Uani 1 1 d . . . . .
C3 C -0.2083(4) 0.5658(4) 0.2895(2) 0.0276(9) Uani 1 1 d . . . . .
C4 C -0.2944(4) 0.5962(4) 0.2400(2) 0.0295(10) Uani 1 1 d . . . . .
C5 C -0.3689(4) 0.5088(5) 0.2144(3) 0.0357(11) Uani 1 1 d . . . . .
H5 H -0.4233 0.5311 0.1821 0.043 Uiso 1 1 calc R U . . .
C6 C -0.3631(5) 0.3856(5) 0.2371(3) 0.0395(12) Uani 1 1 d . . . . .
H6 H -0.4143 0.327 0.2201 0.047 Uiso 1 1 calc R U . . .
C7 C -0.2816(5) 0.3526(5) 0.2844(3) 0.0386(12) Uani 1 1 d . . . . .
H7 H -0.2782 0.2713 0.2993 0.046 Uiso 1 1 calc R U . . .
C8 C -0.3794(5) 0.7507(5) 0.1714(3) 0.0432(13) Uani 1 1 d . . . . .
H8A H -0.3652 0.7105 0.1314 0.065 Uiso 1 1 calc R U . . .
H8B H -0.3786 0.8388 0.1655 0.065 Uiso 1 1 calc R U . . .
H8C H -0.4519 0.7257 0.1847 0.065 Uiso 1 1 calc R U . . .
C9 C 0.0374(4) 0.3889(4) 0.4314(2) 0.0298(10) Uani 1 1 d . . . . .
C10 C -0.0079(4) 0.3628(4) 0.4896(2) 0.0286(10) Uani 1 1 d . . . . .
H10 H -0.0851 0.3739 0.4924 0.034 Uiso 1 1 calc R U . . .
C11 C 0.1639(4) 0.3033(5) 0.5368(3) 0.0351(11) Uani 1 1 d . . . . .
H11 H 0.2085 0.2769 0.5728 0.042 Uiso 1 1 calc R U . . .
C12 C 0.2143(4) 0.3213(5) 0.4798(3) 0.0356(11) Uani 1 1 d . . . . .
H12 H 0.2905 0.3039 0.4772 0.043 Uiso 1 1 calc R U . . .
C13 C 0.1506(4) 0.3658(4) 0.4260(3) 0.0344(11) Uani 1 1 d . . . . .
H13 H 0.1836 0.3798 0.3871 0.041 Uiso 1 1 calc R U . . .
C15 C 0.2091(4) 0.5638(5) 0.2761(2) 0.0348(11) Uani 1 1 d . . . . .
H15 H 0.2362 0.5286 0.2391 0.042 Uiso 1 1 calc R U . . .
C16 C 0.2916(4) 0.5952(4) 0.3281(2) 0.0344(11) Uani 1 1 d . . . . .
C17 C 0.2649(4) 0.6321(4) 0.3908(2) 0.0309(10) Uani 1 1 d . . . . .
C18 C 0.3564(5) 0.6490(5) 0.4391(3) 0.0407(12) Uani 1 1 d . . . . .
C19 C 0.4650(5) 0.6340(6) 0.4240(3) 0.0468(14) Uani 1 1 d . . . . .
H19 H 0.5232 0.6475 0.4556 0.056 Uiso 1 1 calc R U . . .
C20 C 0.4909(5) 0.5986(6) 0.3615(3) 0.0480(14) Uani 1 1 d . . . . .
H20 H 0.5657 0.5889 0.3519 0.058 Uiso 1 1 calc R U . . .
C21 C 0.4049(4) 0.5779(5) 0.3142(3) 0.0386(11) Uani 1 1 d . . . . .
H21 H 0.422 0.5525 0.2731 0.046 Uiso 1 1 calc R U . . .
C22 C 0.4077(6) 0.6860(8) 0.5511(3) 0.0621(18) Uani 1 1 d . . . . .
H22A H 0.4635 0.7465 0.5415 0.093 Uiso 1 1 calc R U . . .
H22B H 0.4429 0.6064 0.5566 0.093 Uiso 1 1 calc R U . . .
H22C H 0.374 0.7088 0.5903 0.093 Uiso 1 1 calc R U . . .
C23 C 0.0369(4) 0.5278(4) 0.2217(2) 0.0278(9) Uani 1 1 d . . . . .
C24 C 0.0428(4) 0.4022(4) 0.2089(2) 0.0317(10) Uani 1 1 d . . . . .
H24 H 0.0939 0.3547 0.2344 0.038 Uiso 1 1 calc R U . . .
C25 C -0.0969(4) 0.4150(5) 0.1270(3) 0.0368(11) Uani 1 1 d . . . . .
H25 H -0.1448 0.3766 0.0957 0.044 Uiso 1 1 calc R U . . .
C26 C -0.1069(5) 0.5415(5) 0.1355(3) 0.0372(11) Uani 1 1 d . . . . .
H26 H -0.158 0.5872 0.1091 0.045 Uiso 1 1 calc R U . . .
C27 C -0.0401(4) 0.5983(5) 0.1834(2) 0.0320(10) Uani 1 1 d . . . . .
H27 H -0.0462 0.683 0.1903 0.038 Uiso 1 1 calc R U . . .
N1 N -0.0291(3) 0.4489(3) 0.38013(19) 0.0276(8) Uani 1 1 d . . . . .
N2 N 0.0542(3) 0.3217(4) 0.5430(2) 0.0312(9) Uani 1 1 d . . . . .
N3 N 0.1018(3) 0.5799(4) 0.27609(19) 0.0297(8) Uani 1 1 d . . . . .
N4 N -0.0213(4) 0.3449(4) 0.1618(2) 0.0312(9) Uani 1 1 d . . . . .
O1 O -0.1411(3) 0.6523(3) 0.31114(16) 0.0311(7) Uani 1 1 d . . . . .
O2 O -0.2942(3) 0.7167(3) 0.21996(17) 0.0365(8) Uani 1 1 d . . . . .
O3 O 0.1641(3) 0.6499(3) 0.40885(17) 0.0304(7) Uani 1 1 d . . . . .
O4 O 0.3234(3) 0.6809(4) 0.4994(2) 0.0478(10) Uani 1 1 d . . . . .
Zn1 Zn 0.01229(4) 0.64636(5) 0.35820(3) 0.0285(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.286(6) . ?
C1 C2 1.447(6) . ?
C1 H1 0.93 . ?
C2 C7 1.408(7) . ?
C2 C3 1.427(7) . ?
C3 O1 1.289(6) . ?
C3 C4 1.434(6) . ?
C4 O2 1.367(6) . ?
C4 C5 1.374(7) . ?
C5 C6 1.411(7) . ?
C5 H5 0.93 . ?
C6 C7 1.376(8) . ?
C6 H6 0.93 . ?
C7 H7 0.93 . ?
C8 O2 1.425(6) . ?
C8 H8A 0.96 . ?
C8 H8B 0.96 . ?
C8 H8C 0.96 . ?
C9 C13 1.379(7) . ?
C9 C10 1.380(7) . ?
C9 N1 1.434(6) . ?
C10 N2 1.362(6) . ?
C10 H10 0.93 . ?
C11 N2 1.333(6) . ?
C11 C12 1.371(8) . ?
C11 H11 0.93 . ?
C12 C13 1.388(7) . ?
C12 H12 0.93 . ?
C13 H13 0.93 . ?
C15 N3 1.286(7) . ?
C15 C16 1.446(7) . ?
C15 H15 0.93 . ?
C16 C21 1.406(7) . ?
C16 C17 1.414(7) . ?
C17 O3 1.292(6) . ?
C17 C18 1.437(8) . ?
C18 C19 1.357(8) . ?
C18 O4 1.377(7) . ?
C19 C20 1.402(8) . ?
C19 H19 0.93 . ?
C20 C21 1.384(8) . ?
C20 H20 0.93 . ?
C21 H21 0.93 . ?
C22 O4 1.416(7) . ?
C22 H22A 0.96 . ?
C22 H22B 0.96 . ?
C22 H22C 0.96 . ?
C23 C24 1.385(7) . ?
C23 C27 1.395(7) . ?
C23 N3 1.435(6) . ?
C24 N4 1.347(6) . ?
C24 H24 0.93 . ?
C25 N4 1.346(6) . ?
C25 C26 1.384(7) . ?
C25 H25 0.93 . ?
C26 C27 1.372(7) . ?
C26 H26 0.93 . ?
C27 H27 0.93 . ?
N1 Zn1 2.242(4) . ?
N2 Zn1 2.265(4) 3_566 ?
N3 Zn1 2.185(4) . ?
N4 Zn1 2.188(4) 2_545 ?
O1 Zn1 2.008(4) . ?
O3 Zn1 2.023(4) . ?
Zn1 N4 2.188(4) 2 ?
Zn1 N2 2.265(4) 3_566 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 126.4(4) . . ?
N1 C1 H1 116.8 . . ?
C2 C1 H1 116.8 . . ?
C7 C2 C3 120.5(4) . . ?
C7 C2 C1 115.6(4) . . ?
C3 C2 C1 123.8(4) . . ?
O1 C3 C2 124.9(4) . . ?
O1 C3 C4 118.5(4) . . ?
C2 C3 C4 116.7(4) . . ?
O2 C4 C5 123.5(4) . . ?
O2 C4 C3 114.7(4) . . ?
C5 C4 C3 121.8(5) . . ?
C4 C5 C6 120.3(5) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 119.8(5) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C2 120.9(5) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C13 C9 C10 118.3(4) . . ?
C13 C9 N1 120.9(4) . . ?
C10 C9 N1 120.6(4) . . ?
N2 C10 C9 123.5(5) . . ?
N2 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
N2 C11 C12 123.3(5) . . ?
N2 C11 H11 118.4 . . ?
C12 C11 H11 118.4 . . ?
C11 C12 C13 119.5(5) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C9 C13 C12 118.6(5) . . ?
C9 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
N3 C15 C16 126.1(5) . . ?
N3 C15 H15 116.9 . . ?
C16 C15 H15 116.9 . . ?
C21 C16 C17 120.1(5) . . ?
C21 C16 C15 115.2(5) . . ?
C17 C16 C15 124.5(5) . . ?
O3 C17 C16 125.2(5) . . ?
O3 C17 C18 116.9(5) . . ?
C16 C17 C18 117.8(5) . . ?
C19 C18 O4 124.8(5) . . ?
C19 C18 C17 120.8(5) . . ?
O4 C18 C17 114.4(5) . . ?
C18 C19 C20 121.0(5) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C21 C20 C19 119.9(5) . . ?
C21 C20 H20 120 . . ?
C19 C20 H20 120 . . ?
C20 C21 C16 120.3(5) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C27 117.8(4) . . ?
C24 C23 N3 120.2(4) . . ?
C27 C23 N3 121.9(4) . . ?
N4 C24 C23 123.7(4) . . ?
N4 C24 H24 118.1 . . ?
C23 C24 H24 118.1 . . ?
N4 C25 C26 123.2(5) . . ?
N4 C25 H25 118.4 . . ?
C26 C25 H25 118.4 . . ?
C27 C26 C25 118.9(5) . . ?
C27 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
C26 C27 C23 119.4(5) . . ?
C26 C27 H27 120.3 . . ?
C23 C27 H27 120.3 . . ?
C1 N1 C9 116.9(4) . . ?
C1 N1 Zn1 124.4(3) . . ?
C9 N1 Zn1 117.5(3) . . ?
C11 N2 C10 116.7(4) . . ?
C11 N2 Zn1 120.9(3) . 3_566 ?
C10 N2 Zn1 118.7(3) . 3_566 ?
C15 N3 C23 115.2(4) . . ?
C15 N3 Zn1 125.4(3) . . ?
C23 N3 Zn1 118.3(3) . . ?
C25 N4 C24 116.9(4) . . ?
C25 N4 Zn1 119.3(3) . 2_545 ?
C24 N4 Zn1 123.7(3) . 2_545 ?
C3 O1 Zn1 131.7(3) . . ?
C4 O2 C8 116.3(4) . . ?
C17 O3 Zn1 131.2(3) . . ?
C18 O4 C22 117.6(5) . . ?
O1 Zn1 O3 176.36(14) . . ?
O1 Zn1 N3 96.14(15) . . ?
O3 Zn1 N3 86.87(15) . . ?
O1 Zn1 N4 86.06(14) . 2 ?
O3 Zn1 N4 91.49(14) . 2 ?
N3 Zn1 N4 98.19(16) . 2 ?
O1 Zn1 N1 85.67(14) . . ?
O3 Zn1 N1 96.50(13) . . ?
N3 Zn1 N1 88.25(15) . . ?
N4 Zn1 N1 170.01(15) 2 . ?
O1 Zn1 N2 94.14(15) . 3_566 ?
O3 Zn1 N2 83.27(15) . 3_566 ?
N3 Zn1 N2 165.55(15) . 3_566 ?
N4 Zn1 N2 92.62(15) 2 3_566 ?
N1 Zn1 N2 82.41(14) . 3_566 ?

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
N1 C1 C2 C7 167.3(5) . . . . ?
N1 C1 C2 C3 -11.8(8) . . . . ?
C7 C2 C3 O1 179.2(4) . . . . ?
C1 C2 C3 O1 -1.7(7) . . . . ?
C7 C2 C3 C4 -1.5(7) . . . . ?
C1 C2 C3 C4 177.6(4) . . . . ?
O1 C3 C4 O2 1.1(6) . . . . ?
C2 C3 C4 O2 -178.2(4) . . . . ?
O1 C3 C4 C5 179.8(4) . . . . ?
C2 C3 C4 C5 0.5(7) . . . . ?
O2 C4 C5 C6 179.3(5) . . . . ?
C3 C4 C5 C6 0.7(8) . . . . ?
C4 C5 C6 C7 -0.8(8) . . . . ?
C5 C6 C7 C2 -0.2(8) . . . . ?
C3 C2 C7 C6 1.4(8) . . . . ?
C1 C2 C7 C6 -177.8(5) . . . . ?
C13 C9 C10 N2 3.6(7) . . . . ?
N1 C9 C10 N2 -170.8(4) . . . . ?
N2 C11 C12 C13 2.7(8) . . . . ?
C10 C9 C13 C12 -2.0(7) . . . . ?
N1 C9 C13 C12 172.3(4) . . . . ?
C11 C12 C13 C9 -0.9(7) . . . . ?
N3 C15 C16 C21 -174.9(5) . . . . ?
N3 C15 C16 C17 9.6(8) . . . . ?
C21 C16 C17 O3 -179.6(5) . . . . ?
C15 C16 C17 O3 -4.4(8) . . . . ?
C21 C16 C17 C18 -1.0(7) . . . . ?
C15 C16 C17 C18 174.2(5) . . . . ?
O3 C17 C18 C19 -179.0(5) . . . . ?
C16 C17 C18 C19 2.3(8) . . . . ?
O3 C17 C18 O4 0.8(7) . . . . ?
C16 C17 C18 O4 -177.9(5) . . . . ?
O4 C18 C19 C20 178.5(6) . . . . ?
C17 C18 C19 C20 -1.7(9) . . . . ?
C18 C19 C20 C21 -0.2(10) . . . . ?
C19 C20 C21 C16 1.5(9) . . . . ?
C17 C16 C21 C20 -0.9(8) . . . . ?
C15 C16 C21 C20 -176.5(5) . . . . ?
C27 C23 C24 N4 0.1(7) . . . . ?
N3 C23 C24 N4 175.1(4) . . . . ?
N4 C25 C26 C27 -2.9(8) . . . . ?
C25 C26 C27 C23 0.9(8) . . . . ?
C24 C23 C27 C26 0.4(7) . . . . ?
N3 C23 C27 C26 -174.5(5) . . . . ?
C2 C1 N1 C9 174.7(4) . . . . ?
C2 C1 N1 Zn1 7.2(7) . . . . ?
C13 C9 N1 C1 125.7(5) . . . . ?
C10 C9 N1 C1 -60.1(6) . . . . ?
C13 C9 N1 Zn1 -66.0(5) . . . . ?
C10 C9 N1 Zn1 108.2(4) . . . . ?
C12 C11 N2 C10 -1.3(7) . . . . ?
C12 C11 N2 Zn1 -159.2(4) . . . 3_566 ?
C9 C10 N2 C11 -1.9(7) . . . . ?
C9 C10 N2 Zn1 156.4(4) . . . 3_566 ?
C16 C15 N3 C23 -173.0(5) . . . . ?
C16 C15 N3 Zn1 -5.1(7) . . . . ?
C24 C23 N3 C15 58.4(6) . . . . ?
C27 C23 N3 C15 -126.8(5) . . . . ?
C24 C23 N3 Zn1 -110.4(4) . . . . ?
C27 C23 N3 Zn1 64.4(5) . . . . ?
C26 C25 N4 C24 3.3(8) . . . . ?
C26 C25 N4 Zn1 -178.7(4) . . . 2_545 ?
C23 C24 N4 C25 -2.0(8) . . . . ?
C23 C24 N4 Zn1 -179.8(4) . . . 2_545 ?
C2 C3 O1 Zn1 19.6(7) . . . . ?
C4 C3 O1 Zn1 -159.7(3) . . . . ?
C5 C4 O2 C8 2.1(7) . . . . ?
C3 C4 O2 C8 -179.2(4) . . . . ?
C16 C17 O3 Zn1 -5.1(7) . . . . ?
C18 C17 O3 Zn1 176.3(3) . . . . ?
C19 C18 O4 C22 -6.9(9) . . . . ?
C17 C18 O4 C22 173.3(6) . . . . ?


# SQUEEZE RESULTS (Version =  30715)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.500 265 74 ' '
2 0.426 0.500 0.000 265 74 ' '
# Missing Reflections Below sin(th)/lambda = 0.25
loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
1 0 0 1.719
0 1 1 2.128
0 0 2 1.974
1 3 2 6.280
2 1 5 6.494
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
TITL
CELL   11.8750   10.8020   20.6840     90.00     93.88     90.00
SPGR P21/c
# Solvent Accessible Volume =     555.5
# Electrons Found in S.A.V. =     146.5
# Note: Atoms in Void as Cxxx and Qxxx all others
C101 0.362 0.533 0.144 !       4.79 eA-3
C102 0.862 0.069 0.451 !       4.49 eA-3
Q103 0.234 0.608 0.014 !       4.02 eA-3
C104 0.357 0.415 0.138 !       3.62 eA-3
C105 0.314 0.350 0.157 !       2.41 eA-3
C106 0.767 0.094 0.387 !       2.21 eA-3
C107 0.609 0.567 0.029 !       1.61 eA-3
Q108 0.902 0.140 0.328 !       1.14 eA-3
Q109 0.829 0.259 0.314 !       1.05 eA-3
Q110 0.879 0.145 0.370 !       0.96 eA-3
C111 0.281 0.477 0.139 !       0.94 eA-3
Q112 0.968 0.149 0.405 !       0.91 eA-3
Q113 0.967 0.253 0.342 !       0.90 eA-3
Q114 0.836 0.423 0.326 !       0.88 eA-3
C115 0.500 0.500 0.000 !       0.86 eA-3
C116 0.578 0.866 0.391 !       0.80 eA-3
Q117 0.873 0.636 0.089 !       0.79 eA-3
Q118 0.080 0.363 0.436 !       0.79 eA-3
Q119 0.955 0.767 0.110 !       0.78 eA-3
C120 0.471 0.986 0.472 !       0.78 eA-3
Q121 0.029 0.334 0.358 !       0.77 eA-3
Q122 0.188 0.764 0.120 !       0.76 eA-3
Q123 0.982 0.770 0.061 !       0.76 eA-3
Q124 0.843 0.759 0.030 !       0.75 eA-3
Q125 0.717 0.778 0.080 !       0.74 eA-3
Q126 0.859 0.349 0.391 !       0.72 eA-3
Q127 0.218 0.642 0.203 !       0.72 eA-3
Q128 0.076 0.751 0.173 !       0.72 eA-3
Q129 0.873 0.975 0.377 !       0.71 eA-3
Q130 0.783 0.601 0.076 !       0.71 eA-3
Q131 0.203 0.439 0.139 !       0.70 eA-3
Q132 0.185 0.936 0.048 !       0.69 eA-3
Q133 0.185 0.258 0.400 !       0.69 eA-3
Q134 0.015 0.146 0.358 !       0.69 eA-3
Q135 0.405 0.490 0.218 !       0.69 eA-3
Q136 0.076 0.537 0.096 !       0.69 eA-3
Q137 0.071 0.368 0.292 !       0.69 eA-3
Q138 0.808 0.069 0.331 !       0.69 eA-3
Q139 0.257 0.662 0.155 !       0.69 eA-3
Q140 0.718 0.565 0.467 !       0.69 eA-3
Q141 0.686 0.647 0.467 !       0.69 eA-3
Q142 0.065 0.330 0.314 !       0.69 eA-3
Q143 0.921 0.251 0.383 !       0.68 eA-3
Q144 0.127 0.758 0.237 !       0.68 eA-3
Q145 0.957 0.361 0.423 !       0.67 eA-3
Q146 0.157 0.088 0.470 !       0.67 eA-3
Q147 0.876 0.715 0.098 !       0.67 eA-3
Q148 0.346 0.431 0.220 !       0.67 eA-3
Q149 0.779 0.861 0.074 !       0.67 eA-3
Q150 0.143 0.209 0.017 !       0.66 eA-3
Q151 0.166 0.542 0.216 !       0.66 eA-3
Q152 0.293 0.795 0.135 !       0.66 eA-3
Q153 0.386 0.847 0.030 !       0.65 eA-3
Q154 0.799 0.642 0.483 !       0.65 eA-3
C155 0.297 0.542 0.048 !       0.65 eA-3
Q156 0.085 0.153 0.453 !       0.65 eA-3
Q157 0.214 0.120 0.486 !       0.65 eA-3
Q158 0.207 0.354 0.468 !       0.64 eA-3
C159 0.643 0.800 0.391 !       0.64 eA-3
Q160 0.922 0.368 0.329 !       0.64 eA-3
Q161 0.078 0.632 0.671 !       0.64 eA-3
Q162 0.343 0.865 0.217 !       0.64 eA-3
Q163 0.313 0.409 0.483 !       0.63 eA-3
Q164 0.185 0.327 0.184 !       0.63 eA-3
Q165 0.295 0.906 0.081 !       0.63 eA-3
Q166 0.497 0.342 0.466 !       0.62 eA-3
Q167 0.747 0.963 0.310 !       0.61 eA-3
Q168 0.314 0.944 0.028 !       0.61 eA-3
Q169 0.059 0.854 0.214 !       0.61 eA-3
Q170 0.950 0.546 0.043 !       0.61 eA-3
Q171 0.797 0.434 0.501 !       0.61 eA-3
Q172 0.049 0.048 0.450 !       0.61 eA-3
Q173 0.829 0.922 0.187 !       0.60 eA-3
C174 0.436 0.522 0.091 !       0.60 eA-3
Q175 0.219 0.866 0.186 !       0.59 eA-3
Q176 0.183 0.433 0.215 !       0.59 eA-3
Q177 0.158 0.391 0.033 !       0.59 eA-3
Q178 0.704 0.256 0.329 !       0.59 eA-3
Q179 0.834 0.770 0.202 !       0.59 eA-3
Q180 0.472 0.429 0.219 !       0.59 eA-3
Q181 0.669 0.843 0.015 !       0.59 eA-3
Q182 0.309 0.253 0.014 !       0.59 eA-3
Q183 0.688 0.221 0.262 !       0.58 eA-3
Q184 0.143 0.265 0.325 !       0.58 eA-3
Q185 0.063 0.163 0.124 !       0.58 eA-3
Q186 0.296 0.226 0.032 !       0.57 eA-3
Q187 0.613 0.439 0.200 !       0.57 eA-3
C188 0.996 0.453 0.000 !       0.56 eA-3
Q189 0.383 0.017 0.045 !       0.56 eA-3
Q190 0.731 0.398 0.360 !       0.56 eA-3
Q191 0.124 0.359 0.386 !       0.56 eA-3
Q192 0.316 0.934 0.056 !       0.56 eA-3
Q193 0.857 0.821 0.129 !       0.56 eA-3
Q194 0.204 0.420 0.267 !       0.55 eA-3
Q195 0.667 0.920 0.235 !       0.54 eA-3
Q196 0.251 0.809 0.202 !       0.54 eA-3
Q197 0.919 0.831 0.375 !       0.53 eA-3
Q198 0.703 0.260 0.785 !       0.53 eA-3
Q199 0.469 0.403 0.251 !       0.53 eA-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
####################################################################### 
# 
# 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_am_4
_database_code_depnum_ccdc_archive 'CCDC 1903319'
loop_
_audit_author_name
_audit_author_address
'Anna Dolega'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-03-14 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;

_audit_creation_date             2016-09-06T17:15:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_moiety         'C26 H22 N4 O4 Zn'
_chemical_formula_sum            'C26 H22 N4 O4 Zn'
_chemical_formula_weight         519.84

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

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

_cell_length_a                   12.7455(16)
_cell_length_b                   15.1440(14)
_cell_length_c                   12.9090(17)
_cell_angle_alpha                90
_cell_angle_beta                 113.752(10)
_cell_angle_gamma                90
_cell_volume                     2280.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1538
_cell_measurement_theta_min      3.73
_cell_measurement_theta_max      29.41

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

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.82
_exptl_crystal_size_mid          0.65
_exptl_crystal_size_min          0.525
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_F_000             1072
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 16 25 0.288
5 -9 -17 0.308
27 10 -8 0.42
-28 -10 9 0.401
-7 25 -8 0.295
10 -27 8 0.23
20 8 -8 0.408
9 -8 1 0.316
3 22 -9 0.341
10 20 21 0.362
16 -5 -20 0.376


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

_exptl_absorpt_coefficient_mu    1.119
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(HABITUS; Herrendorf, 1997)'
_exptl_absorpt_correction_T_min  0.4923
_exptl_absorpt_correction_T_max  0.5963

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

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_number            12211
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.203
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.999
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_reflns_Friedel_coverage         0
_reflns_number_total             4457
_reflns_number_gt                3595
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

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

_atom_sites_solution_primary     heavy
_atom_sites_solution_hydrogens   geom

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1100P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4457
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.143
_refine_ls_wR_factor_gt          0.1269
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.67
_refine_diff_density_min         -1.02
_refine_diff_density_rms         0.124

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.33039(3) 0.10157(2) 0.04780(3) 0.01932(15) Uani 1 1 d . . . . .
N2 N 0.1787(2) 0.11509(16) 0.0591(2) 0.0205(5) Uani 1 1 d . . . . .
O2 O 0.40694(17) 0.04248(14) 0.19288(17) 0.0207(4) Uani 1 1 d . . . . .
C6 C 0.4947(2) 0.17891(19) -0.0781(2) 0.0199(6) Uani 1 1 d . . . . .
C1 C 0.4694(2) 0.23579(19) -0.0024(2) 0.0212(6) Uani 1 1 d . . . . .
C8 C 0.4419(2) 0.09470(18) -0.1140(2) 0.0196(6) Uani 1 1 d . . . . .
H8 H 0.4607 0.0637 -0.1663 0.024 Uiso 1 1 calc R . . . .
O4 O 0.52927(18) -0.06076(15) 0.35804(17) 0.0259(5) Uani 1 1 d . . . . .
O1 O 0.39977(18) 0.21746(14) 0.04521(18) 0.0250(5) Uani 1 1 d . . . . .
O3 O 0.5025(2) 0.37180(16) 0.0959(2) 0.0354(6) Uani 1 1 d . . . . .
C24 C 0.2548(3) -0.1412(2) -0.2584(3) 0.0367(8) Uani 1 1 d . . . . .
H24 H 0.2555 -0.1715 -0.3208 0.044 Uiso 1 1 calc R . . . .
N3 N -0.0217(2) 0.1377(2) -0.0398(3) 0.0350(7) Uani 1 1 d . . . . .
N1 N 0.3694(2) 0.05786(16) -0.0792(2) 0.0192(5) Uani 1 1 d . . . . .
C22 C 0.3142(2) -0.02256(19) -0.1266(2) 0.0208(6) Uani 1 1 d . . . . .
C12 C 0.3720(3) -0.0808(2) 0.4168(3) 0.0303(7) Uani 1 1 d . . . . .
H12 H 0.4158 -0.117 0.4769 0.036 Uiso 1 1 calc R . . . .
N4 N 0.2465(2) -0.04930(18) -0.0755(2) 0.0254(6) Uani 1 1 d . . . . .
C21 C 0.1845(3) -0.1226(2) -0.1149(3) 0.0301(7) Uani 1 1 d . . . . .
H21 H 0.1379 -0.1425 -0.0798 0.036 Uiso 1 1 calc R . . . .
C10 C 0.2394(3) 0.0282(2) 0.2348(2) 0.0231(6) Uani 1 1 d . . . . .
C3 C 0.5989(3) 0.3448(2) -0.0295(3) 0.0301(7) Uani 1 1 d . . . . .
H3 H 0.6335 0.4001 -0.0138 0.036 Uiso 1 1 calc R . . . .
C9 C 0.3558(2) 0.01131(19) 0.2538(2) 0.0200(6) Uani 1 1 d . . . . .
C23 C 0.3224(3) -0.0665(2) -0.2179(3) 0.0278(7) Uani 1 1 d . . . . .
H23 H 0.3712 -0.0467 -0.2505 0.033 Uiso 1 1 calc R . . . .
C5 C 0.5719(3) 0.2059(2) -0.1264(3) 0.0259(6) Uani 1 1 d . . . . .
H5 H 0.5889 0.1674 -0.1736 0.031 Uiso 1 1 calc R . . . .
C19 C -0.0944(3) 0.2361(2) -0.1995(3) 0.0338(8) Uani 1 1 d . . . . .
H19 H -0.1572 0.2617 -0.2571 0.041 Uiso 1 1 calc R . . . .
C15 C 0.1601(3) 0.0773(2) 0.1406(3) 0.0244(6) Uani 1 1 d . . . . .
H15 H 0.0861 0.0826 0.1374 0.029 Uiso 1 1 calc R . . . .
C16 C 0.0837(2) 0.1574(2) -0.0290(3) 0.0226(6) Uani 1 1 d . . . . .
C14 C 0.5907(3) -0.1284(3) 0.4369(3) 0.0356(8) Uani 1 1 d . . . . .
H14A H 0.5459 -0.1816 0.4199 0.053 Uiso 1 1 calc GR . . . .
H14B H 0.6049 -0.1096 0.5123 0.053 Uiso 1 1 calc GR . . . .
H14C H 0.6623 -0.1394 0.4311 0.053 Uiso 1 1 calc GR . . . .
C11 C 0.2573(3) -0.0625(3) 0.3973(3) 0.0336(8) Uani 1 1 d . . . . .
H11 H 0.2252 -0.0864 0.4443 0.04 Uiso 1 1 calc R . . . .
C17 C 0.1065(3) 0.2148(3) -0.1009(3) 0.0361(8) Uani 1 1 d . . . . .
H17 H 0.1814 0.2261 -0.0918 0.043 Uiso 1 1 calc R . . . .
C20 C -0.1086(3) 0.1776(3) -0.1242(3) 0.0367(8) Uani 1 1 d . . . . .
H20 H -0.1829 0.165 -0.1323 0.044 Uiso 1 1 calc R . . . .
C4 C 0.6217(3) 0.2878(2) -0.1044(3) 0.0288(7) Uani 1 1 d . . . . .
H4 H 0.6701 0.3056 -0.1385 0.035 Uiso 1 1 calc R . . . .
C18 C 0.0149(3) 0.2551(3) -0.1866(3) 0.0415(9) Uani 1 1 d . . . . .
H18 H 0.0278 0.2949 -0.2351 0.05 Uiso 1 1 calc R . . . .
C2 C 0.5270(2) 0.3204(2) 0.0207(3) 0.0246(6) Uani 1 1 d . . . . .
C25 C 0.1867(3) -0.1699(2) -0.2052(3) 0.0361(8) Uani 1 1 d . . . . .
H25 H 0.1426 -0.2207 -0.2299 0.043 Uiso 1 1 calc R . . . .
C7 C 0.5841(3) 0.4388(3) 0.1514(4) 0.0460(10) Uani 1 1 d . . . . .
H7A H 0.5779 0.4855 0.0989 0.069 Uiso 1 1 calc GR . . . .
H7B H 0.6599 0.4142 0.1793 0.069 Uiso 1 1 calc GR . . . .
H7C H 0.5696 0.4619 0.2136 0.069 Uiso 1 1 calc GR . . . .
C13 C 0.4196(3) -0.0454(2) 0.3474(2) 0.0223(6) Uani 1 1 d . . . . .
C0AA C 0.1933(3) -0.0092(2) 0.3087(3) 0.0310(7) Uani 1 1 d . . . . .
H0AA H 0.1176 0.0028 0.2964 0.037 Uiso 1 1 calc R . . . .



#----------------------------------------------------------------------------#
#                   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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N2 2.007(3) . ?
Zn1 O2 1.946(2) . ?
Zn1 O1 1.972(2) . ?
Zn1 N1 2.008(3) . ?
N2 C15 1.300(4) . ?
N2 C16 1.435(4) . ?
O2 C9 1.296(4) . ?
C6 C1 1.434(4) . ?
C6 C8 1.430(4) . ?
C6 C5 1.421(4) . ?
C1 O1 1.296(4) . ?
C1 C2 1.447(4) . ?
C8 H8 0.93 . ?
C8 N1 1.303(4) . ?
O4 C14 1.434(4) . ?
O4 C13 1.369(4) . ?
O3 C2 1.375(4) . ?
O3 C7 1.423(4) . ?
C24 H24 0.93 . ?
C24 C23 1.390(5) . ?
C24 C25 1.376(5) . ?
N3 C16 1.327(4) . ?
N3 C20 1.344(4) . ?
N1 C22 1.416(4) . ?
C22 N4 1.343(4) . ?
C22 C23 1.393(4) . ?
C12 H12 0.93 . ?
C12 C11 1.407(5) . ?
C12 C13 1.377(5) . ?
N4 C21 1.339(4) . ?
C21 H21 0.93 . ?
C21 C25 1.378(5) . ?
C10 C9 1.426(4) . ?
C10 C15 1.436(4) . ?
C10 C0AA 1.424(4) . ?
C3 H3 0.93 . ?
C3 C4 1.411(5) . ?
C3 C2 1.370(5) . ?
C9 C13 1.437(4) . ?
C23 H23 0.93 . ?
C5 H5 0.93 . ?
C5 C4 1.370(5) . ?
C19 H19 0.93 . ?
C19 C20 1.380(5) . ?
C19 C18 1.366(5) . ?
C15 H15 0.93 . ?
C16 C17 1.386(5) . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
C11 H11 0.93 . ?
C11 C0AA 1.369(5) . ?
C17 H17 0.93 . ?
C17 C18 1.385(5) . ?
C20 H20 0.93 . ?
C4 H4 0.93 . ?
C18 H18 0.93 . ?
C25 H25 0.93 . ?
C7 H7A 0.96 . ?
C7 H7B 0.96 . ?
C7 H7C 0.96 . ?
C0AA H0AA 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
N2 Zn1 N1 130.98(10) . . ?
O2 Zn1 N2 95.80(9) . . ?
O2 Zn1 O1 111.79(9) . . ?
O2 Zn1 N1 116.18(9) . . ?
O1 Zn1 N2 111.24(10) . . ?
O1 Zn1 N1 91.10(10) . . ?
C15 N2 Zn1 120.6(2) . . ?
C15 N2 C16 117.8(3) . . ?
C16 N2 Zn1 121.2(2) . . ?
C9 O2 Zn1 124.87(18) . . ?
C8 C6 C1 123.4(3) . . ?
C5 C6 C1 120.8(3) . . ?
C5 C6 C8 115.7(3) . . ?
C6 C1 C2 115.9(3) . . ?
O1 C1 C6 125.4(3) . . ?
O1 C1 C2 118.6(3) . . ?
C6 C8 H8 117.4 . . ?
N1 C8 C6 125.2(3) . . ?
N1 C8 H8 117.4 . . ?
C13 O4 C14 115.9(3) . . ?
C1 O1 Zn1 126.58(19) . . ?
C2 O3 C7 115.6(3) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C25 C24 C23 119.3(3) . . ?
C16 N3 C20 117.0(3) . . ?
C8 N1 Zn1 125.7(2) . . ?
C8 N1 C22 121.1(3) . . ?
C22 N1 Zn1 113.14(19) . . ?
N4 C22 N1 110.7(3) . . ?
N4 C22 C23 123.6(3) . . ?
C23 C22 N1 125.7(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C13 C12 C11 120.3(3) . . ?
C21 N4 C22 117.4(3) . . ?
N4 C21 H21 118.6 . . ?
N4 C21 C25 122.9(3) . . ?
C25 C21 H21 118.6 . . ?
C9 C10 C15 124.6(3) . . ?
C0AA C10 C9 119.6(3) . . ?
C0AA C10 C15 115.7(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.4(3) . . ?
O2 C9 C10 125.0(3) . . ?
O2 C9 C13 118.4(3) . . ?
C10 C9 C13 116.7(3) . . ?
C24 C23 C22 117.5(3) . . ?
C24 C23 H23 121.3 . . ?
C22 C23 H23 121.3 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.5 . . ?
C20 C19 H19 121.1 . . ?
C18 C19 H19 121.1 . . ?
C18 C19 C20 117.8(3) . . ?
N2 C15 C10 128.1(3) . . ?
N2 C15 H15 115.9 . . ?
C10 C15 H15 115.9 . . ?
N3 C16 N2 118.6(3) . . ?
N3 C16 C17 123.1(3) . . ?
C17 C16 N2 118.3(3) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C11 H11 120.2 . . ?
C0AA C11 C12 119.5(3) . . ?
C0AA C11 H11 120.2 . . ?
C16 C17 H17 120.8 . . ?
C18 C17 C16 118.4(3) . . ?
C18 C17 H17 120.8 . . ?
N3 C20 C19 124.1(3) . . ?
N3 C20 H20 118 . . ?
C19 C20 H20 118 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.3 . . ?
C19 C18 C17 119.6(3) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
O3 C2 C1 114.0(3) . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 O3 124.5(3) . . ?
C24 C25 C21 119.3(3) . . ?
C24 C25 H25 120.3 . . ?
C21 C25 H25 120.3 . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C13 C12 124.6(3) . . ?
O4 C13 C9 113.3(3) . . ?
C12 C13 C9 122.1(3) . . ?
C10 C0AA H0AA 119.1 . . ?
C11 C0AA C10 121.8(3) . . ?
C11 C0AA H0AA 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
Zn1 N2 C15 C10 4.7(5) . . . . ?
Zn1 N2 C16 N3 155.9(2) . . . . ?
Zn1 N2 C16 C17 -22.2(4) . . . . ?
Zn1 O2 C9 C10 -11.4(4) . . . . ?
Zn1 O2 C9 C13 168.0(2) . . . . ?
Zn1 N1 C22 N4 1.2(3) . . . . ?
Zn1 N1 C22 C23 177.8(2) . . . . ?
N2 C16 C17 C18 179.5(3) . . . . ?
O2 C9 C13 O4 -1.4(4) . . . . ?
O2 C9 C13 C12 179.6(3) . . . . ?
C6 C1 O1 Zn1 10.9(4) . . . . ?
C6 C1 C2 O3 -178.4(3) . . . . ?
C6 C1 C2 C3 1.5(4) . . . . ?
C6 C8 N1 Zn1 -8.9(4) . . . . ?
C6 C8 N1 C22 174.7(3) . . . . ?
C6 C5 C4 C3 2.2(5) . . . . ?
C1 C6 C8 N1 -3.3(4) . . . . ?
C1 C6 C5 C4 -1.8(4) . . . . ?
C8 C6 C1 O1 2.4(4) . . . . ?
C8 C6 C1 C2 -177.2(3) . . . . ?
C8 C6 C5 C4 175.5(3) . . . . ?
C8 N1 C22 N4 178.1(3) . . . . ?
C8 N1 C22 C23 -5.4(4) . . . . ?
O1 C1 C2 O3 2.0(4) . . . . ?
O1 C1 C2 C3 -178.1(3) . . . . ?
N3 C16 C17 C18 1.4(6) . . . . ?
N1 C22 N4 C21 177.0(3) . . . . ?
N1 C22 C23 C24 -175.0(3) . . . . ?
C22 N4 C21 C25 -0.9(5) . . . . ?
C12 C11 C0AA C10 0.2(6) . . . . ?
N4 C22 C23 C24 1.1(5) . . . . ?
N4 C21 C25 C24 -0.3(6) . . . . ?
C10 C9 C13 O4 178.0(3) . . . . ?
C10 C9 C13 C12 -1.0(4) . . . . ?
C9 C10 C15 N2 -1.1(5) . . . . ?
C9 C10 C0AA C11 -0.9(5) . . . . ?
C23 C24 C25 C21 1.8(6) . . . . ?
C23 C22 N4 C21 0.4(4) . . . . ?
C5 C6 C1 O1 179.5(3) . . . . ?
C5 C6 C1 C2 -0.1(4) . . . . ?
C5 C6 C8 N1 179.5(3) . . . . ?
C15 N2 C16 N3 -16.7(4) . . . . ?
C15 N2 C16 C17 165.1(3) . . . . ?
C15 C10 C9 O2 4.6(5) . . . . ?
C15 C10 C9 C13 -174.8(3) . . . . ?
C15 C10 C0AA C11 175.5(3) . . . . ?
C16 N2 C15 C10 177.3(3) . . . . ?
C16 N3 C20 C19 0.7(6) . . . . ?
C16 C17 C18 C19 -1.3(6) . . . . ?
C14 O4 C13 C12 9.4(4) . . . . ?
C14 O4 C13 C9 -169.6(3) . . . . ?
C11 C12 C13 O4 -178.6(3) . . . . ?
C11 C12 C13 C9 0.3(5) . . . . ?
C20 N3 C16 N2 -179.1(3) . . . . ?
C20 N3 C16 C17 -1.1(5) . . . . ?
C20 C19 C18 C17 1.0(6) . . . . ?
C4 C3 C2 C1 -1.2(5) . . . . ?
C4 C3 C2 O3 178.8(3) . . . . ?
C18 C19 C20 N3 -0.6(6) . . . . ?
C2 C1 O1 Zn1 -169.54(19) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C25 C24 C23 C22 -2.2(5) . . . . ?
C7 O3 C2 C1 158.5(3) . . . . ?
C7 O3 C2 C3 -21.4(5) . . . . ?
C13 C12 C11 C0AA 0.1(5) . . . . ?
C0AA C10 C9 O2 -179.3(3) . . . . ?
C0AA C10 C9 C13 1.2(4) . . . . ?
C0AA C10 C15 N2 -177.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_am_15
_database_code_depnum_ccdc_archive 'CCDC 1903321'
loop_
_audit_author_name
_audit_author_address
'Anna Dolega'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-03-14 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;

_audit_creation_date             2018-09-06T14:25:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C62 H66 Cu2 N8 O19 Zn2'
_chemical_formula_weight         1485.04

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'I 2/a'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   20.374(6)
_cell_length_b                   14.738(3)
_cell_length_c                   22.538(7)
_cell_angle_alpha                90
_cell_angle_beta                 110.75(2)
_cell_angle_gamma                90
_cell_volume                     6329(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    190
_cell_measurement_theta_min      3.37
_cell_measurement_theta_max      27.06

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

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.034
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_F_000             3056
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
13 -18 19 0.024
-9 6 19 0.106
20 14 -6 0.019
-20 -11 12 0.015
-4 4 15 0.106
5 -3 -15 0.05
-12 16 -15 0.02
17 -22 18 0.02
7 4 -4 0.016


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

_exptl_absorpt_coefficient_mu    1.492
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
        Structure Analysis", published in
        F. R. Ahmed (Editor), "Crystallographic Computing",
        Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.8909
_exptl_absorpt_correction_T_max  0.9774

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

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_number            20831
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.138
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 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
_reflns_Friedel_coverage         0
_reflns_number_total             6211
_reflns_number_gt                4288
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       
;
        X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
        X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        'STOE X-Area'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image
processing, for the correction and scaling of reflection intensities and
        for outlier rejection, version 1.77, Darmstadt 2016
;

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

_atom_sites_solution_hydrogens   mixed

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0246P)²+70.8998P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6211
_refine_ls_number_parameters     434
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1305
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.812
_refine_diff_density_rms         0.116

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.86594(3) 0.48838(4) 0.95722(3) 0.02070(16) Uani 1 1 d . . . . .
Zn1 Zn 0.90688(3) 0.58568(4) 1.22469(3) 0.02303(16) Uani 1 1 d . . . . .
O7 O 0.94214(18) 0.5282(2) 1.02686(16) 0.0242(8) Uani 1 1 d . . . . .
O5 O 0.79993(18) 0.4359(2) 0.88403(16) 0.0240(8) Uani 1 1 d . . . . .
O3 O 0.9780(2) 0.5442(3) 1.30352(17) 0.0392(11) Uani 1 1 d . . . . .
N2 N 0.9139(2) 0.4710(3) 1.17477(18) 0.0213(9) Uani 1 1 d . . . . .
O1 O 0.9346(2) 0.7006(3) 1.19735(17) 0.0311(9) Uani 1 1 d . . . . .
N3 N 0.8634(2) 0.6022(3) 0.90852(18) 0.0210(9) Uani 1 1 d . . . . .
O8 O 1.03928(18) 0.5505(2) 1.13874(16) 0.0256(8) Uani 1 1 d . . . . .
N4 N 0.6931(2) 0.6065(3) 0.77808(18) 0.0220(9) Uani 1 1 d . . . . .
N1 N 0.8558(2) 0.3846(3) 1.01120(18) 0.0205(9) Uani 1 1 d . . . . .
C5 C 0.7705(2) 0.3564(4) 0.8759(2) 0.0199(11) Uani 1 1 d . . . . .
C23 C 0.9603(3) 0.6768(3) 0.9914(2) 0.0201(11) Uani 1 1 d . . . . .
C19 C 1.0287(3) 0.6213(4) 1.0968(2) 0.0217(11) Uani 1 1 d . . . . .
C11 C 0.8251(3) 0.3088(4) 0.9883(2) 0.0205(11) Uani 1 1 d . . . . .
H11 H 0.8317 0.261 1.0168 0.025 Uiso 1 1 calc R U . . .
C24 C 0.9065(3) 0.6704(4) 0.9305(2) 0.0226(11) Uani 1 1 d . . . . .
H24 H 0.9015 0.7197 0.9035 0.027 Uiso 1 1 calc R U . . .
C29 C 0.7803(3) 0.6438(4) 0.7347(2) 0.0276(12) Uani 1 1 d . . . . .
H29 H 0.7915 0.6594 0.6994 0.033 Uiso 1 1 calc R U . . .
C9 C 0.7489(3) 0.2039(4) 0.9096(2) 0.0247(11) Uani 1 1 d . . . . .
H9 H 0.7584 0.16 0.9411 0.03 Uiso 1 1 calc R U . . .
C18 C 0.9748(3) 0.6059(3) 1.0363(2) 0.0203(11) Uani 1 1 d . . . . .
C13 C 0.8918(3) 0.3872(4) 1.0785(2) 0.0207(11) Uani 1 1 d . . . . .
C3 C 0.9864(3) 0.5861(4) 1.3555(2) 0.0293(12) Uani 1 1 d . . . . .
C7 C 0.6899(3) 0.2512(4) 0.8018(2) 0.0264(12) Uani 1 1 d . . . . .
H7 H 0.6587 0.2382 0.7612 0.032 Uiso 1 1 calc R U . . .
C16 C 0.9676(3) 0.3267(4) 1.1771(2) 0.0223(11) Uani 1 1 d . . . . .
H16 H 0.9967 0.281 1.2006 0.027 Uiso 1 1 calc R U . . .
C1 C 0.8974(3) 0.7230(4) 1.1402(3) 0.0293(13) Uani 1 1 d . . . . .
C15 C 0.9555(3) 0.4033(4) 1.2062(2) 0.0223(11) Uani 1 1 d . . . . .
H15 H 0.9773 0.4085 1.25 0.027 Uiso 1 1 calc R U . . .
C17 C 0.9354(3) 0.3188(4) 1.1114(2) 0.0230(11) Uani 1 1 d . . . . .
H17 H 0.9433 0.2681 1.0903 0.028 Uiso 1 1 calc R U . . .
C28 C 0.7119(3) 0.6279(4) 0.7285(2) 0.0256(12) Uani 1 1 d . . . . .
H28 H 0.6773 0.6322 0.6885 0.031 Uiso 1 1 calc R U . . .
C20 C 1.0651(3) 0.7011(4) 1.1095(2) 0.0256(12) Uani 1 1 d . . . . .
H20 H 1.1005 0.7092 1.1488 0.031 Uiso 1 1 calc R U . . .
C10 C 0.7823(3) 0.2906(4) 0.9238(2) 0.0219(11) Uani 1 1 d . . . . .
C27 C 0.7440(3) 0.5992(4) 0.8357(2) 0.0230(11) Uani 1 1 d . . . . .
H27 H 0.7314 0.5841 0.8703 0.028 Uiso 1 1 calc R U . . .
C14 C 0.8819(3) 0.4628(4) 1.1115(2) 0.0211(11) Uani 1 1 d . . . . .
H14 H 0.8523 0.5089 1.0891 0.025 Uiso 1 1 calc R U . . .
C26 C 0.8144(3) 0.6135(4) 0.8453(2) 0.0220(11) Uani 1 1 d . . . . .
C8 C 0.7032(3) 0.1852(4) 0.8501(2) 0.0287(12) Uani 1 1 d . . . . .
H8 H 0.6808 0.1292 0.8414 0.034 Uiso 1 1 calc R U . . .
C30 C 0.8334(3) 0.6363(4) 0.7947(2) 0.0263(12) Uani 1 1 d . . . . .
H30 H 0.8802 0.6466 0.7999 0.032 Uiso 1 1 calc R U . . .
O6 O 0.71307(19) 0.4016(3) 0.77013(16) 0.0288(9) Uani 1 1 d . . . . .
O2 O 0.8536(2) 0.6729(3) 1.10275(18) 0.0318(9) Uani 1 1 d . . . . .
O4 O 0.9503(2) 0.6501(3) 1.36043(18) 0.0389(10) Uani 1 1 d . . . . .
C22 C 0.9978(3) 0.7597(4) 1.0065(2) 0.0240(11) Uani 1 1 d . . . . .
H22 H 0.9868 0.8066 0.9769 0.029 Uiso 1 1 calc R U . . .
C6 C 0.7220(3) 0.3333(4) 0.8137(2) 0.0230(11) Uani 1 1 d . . . . .
C25 C 1.0847(3) 0.5681(4) 1.2027(2) 0.0294(13) Uani 1 1 d . . . . .
H25A H 1.1316 0.5783 1.2037 0.044 Uiso 1 1 calc R U . . .
H25B H 1.0843 0.5169 1.2289 0.044 Uiso 1 1 calc R U . . .
H25C H 1.0686 0.621 1.2184 0.044 Uiso 1 1 calc R U . . .
C12 C 0.6651(3) 0.3855(4) 0.7073(2) 0.0282(12) Uani 1 1 d . . . . .
H12A H 0.6624 0.4386 0.6818 0.042 Uiso 1 1 calc R U . . .
H12B H 0.6195 0.3722 0.7086 0.042 Uiso 1 1 calc R U . . .
H12C H 0.6812 0.3351 0.6892 0.042 Uiso 1 1 calc R U . . .
C21 C 1.0500(3) 0.7716(4) 1.0640(2) 0.0282(12) Uani 1 1 d . . . . .
H21 H 1.0754 0.8255 1.0731 0.034 Uiso 1 1 calc R U . . .
C2 C 0.9073(3) 0.8179(4) 1.1202(3) 0.0374(14) Uani 1 1 d . . . . .
H2A H 0.8718 0.8568 1.1254 0.056 Uiso 1 1 calc R U . . .
H2B H 0.9034 0.8176 1.0765 0.056 Uiso 1 1 calc R U . . .
H2C H 0.9528 0.8397 1.1461 0.056 Uiso 1 1 calc R U . . .
C4 C 1.0459(4) 0.5517(5) 1.4126(3) 0.054(2) Uani 1 1 d . . . . .
H4A H 1.0325 0.4954 1.4265 0.082 Uiso 1 1 calc R U . . .
H4B H 1.0565 0.5955 1.4461 0.082 Uiso 1 1 calc R U . . .
H4C H 1.0866 0.5421 1.4013 0.082 Uiso 1 1 calc R U . . .
O9 O 0.7939(6) 0.8543(7) 0.9189(4) 0.145(4) Uani 1 1 d . . . . .
H9A H 0.7811 0.8257 0.9441 0.217 Uiso 1 1 calc R U . . .
C31 C 0.8166(8) 0.9402(8) 0.9436(5) 0.140(6) Uani 1 1 d . . . . .
H31A H 0.8136 0.9811 0.9096 0.21 Uiso 1 1 calc R U . . .
H31B H 0.8644 0.9367 0.9722 0.21 Uiso 1 1 calc R U . . .
H31C H 0.7875 0.962 0.966 0.21 Uiso 1 1 calc R U . . .
O10A O 0.75 0.7521(6) 1 0.047(2) Uani 0.816(9) 2 d GS T P A 1
H10A H 0.78 0.7202 1.0282 0.071 Uiso 0.816(9) 1 d G U P A 1
O10B O 0.75 0.598(3) 1 0.047(2) Uani 0.184(9) 2 d GS T P A 2
H10B H 0.7808 0.6266 0.9902 0.071 Uiso 0.184(9) 1 d G U P A 2



#----------------------------------------------------------------------------#
#                   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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O7 1.868(3) . ?
Cu1 O5 1.886(3) . ?
Cu1 N3 1.995(4) . ?
Cu1 N1 2.010(4) . ?
Zn1 O3 1.951(4) . ?
Zn1 O1 1.953(4) . ?
Zn1 N4 2.040(4) 2_657 ?
Zn1 N2 2.063(4) . ?
O7 C18 1.304(6) . ?
O5 C5 1.300(6) . ?
O3 C3 1.282(6) . ?
N2 C15 1.339(7) . ?
N2 C14 1.348(6) . ?
O1 C1 1.284(6) . ?
N3 C24 1.311(7) . ?
N3 C26 1.431(6) . ?
O8 C19 1.372(6) . ?
O8 C25 1.434(6) . ?
N4 C28 1.340(6) . ?
N4 C27 1.348(6) . ?
N4 Zn1 2.040(4) 2_657 ?
N1 C11 1.295(7) . ?
N1 C13 1.432(6) . ?
C5 C10 1.407(7) . ?
C5 C6 1.441(6) . ?
C23 C18 1.411(7) . ?
C23 C22 1.418(7) . ?
C23 C24 1.424(7) . ?
C19 C20 1.365(7) . ?
C19 C18 1.434(7) . ?
C11 C10 1.430(7) . ?
C29 C28 1.371(7) . ?
C29 C30 1.405(7) . ?
C9 C8 1.362(7) . ?
C9 C10 1.429(7) . ?
C13 C17 1.374(7) . ?
C13 C14 1.393(7) . ?
C3 O4 1.225(7) . ?
C3 C4 1.508(8) . ?
C7 C6 1.356(7) . ?
C7 C8 1.414(8) . ?
C16 C15 1.372(7) . ?
C16 C17 1.395(7) . ?
C1 O2 1.233(7) . ?
C1 C2 1.504(8) . ?
C20 C21 1.416(8) . ?
C27 C26 1.390(7) . ?
C26 C30 1.371(7) . ?
O6 C6 1.373(6) . ?
O6 C12 1.426(6) . ?
C22 C21 1.365(7) . ?
O9 C31 1.394(12) . ?

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
O7 Cu1 O5 170.53(16) . . ?
O7 Cu1 N3 92.87(16) . . ?
O5 Cu1 N3 89.55(16) . . ?
O7 Cu1 N1 87.90(16) . . ?
O5 Cu1 N1 91.31(16) . . ?
N3 Cu1 N1 169.92(17) . . ?
O3 Zn1 O1 110.76(18) . . ?
O3 Zn1 N4 119.14(17) . 2_657 ?
O1 Zn1 N4 104.90(17) . 2_657 ?
O3 Zn1 N2 93.87(17) . . ?
O1 Zn1 N2 117.07(16) . . ?
N4 Zn1 N2 111.58(17) 2_657 . ?
C18 O7 Cu1 129.6(3) . . ?
C5 O5 Cu1 130.1(3) . . ?
C3 O3 Zn1 119.8(4) . . ?
C15 N2 C14 118.1(4) . . ?
C15 N2 Zn1 118.3(3) . . ?
C14 N2 Zn1 123.4(4) . . ?
C1 O1 Zn1 113.9(4) . . ?
C24 N3 C26 115.1(4) . . ?
C24 N3 Cu1 123.6(3) . . ?
C26 N3 Cu1 121.2(3) . . ?
C19 O8 C25 116.3(4) . . ?
C28 N4 C27 118.2(4) . . ?
C28 N4 Zn1 126.0(3) . 2_657 ?
C27 N4 Zn1 115.8(3) . 2_657 ?
C11 N1 C13 116.1(4) . . ?
C11 N1 Cu1 123.6(3) . . ?
C13 N1 Cu1 119.7(3) . . ?
O5 C5 C10 124.7(4) . . ?
O5 C5 C6 118.2(5) . . ?
C10 C5 C6 117.1(5) . . ?
C18 C23 C22 120.5(5) . . ?
C18 C23 C24 122.4(5) . . ?
C22 C23 C24 117.0(5) . . ?
C20 C19 O8 124.7(5) . . ?
C20 C19 C18 120.8(5) . . ?
O8 C19 C18 114.5(4) . . ?
N1 C11 C10 127.0(5) . . ?
N3 C24 C23 126.8(5) . . ?
C28 C29 C30 119.4(5) . . ?
C8 C9 C10 120.5(5) . . ?
O7 C18 C23 124.6(4) . . ?
O7 C18 C19 118.0(4) . . ?
C23 C18 C19 117.4(5) . . ?
C17 C13 C14 119.1(4) . . ?
C17 C13 N1 122.9(5) . . ?
C14 C13 N1 118.0(4) . . ?
O4 C3 O3 124.3(5) . . ?
O4 C3 C4 120.6(5) . . ?
O3 C3 C4 115.1(5) . . ?
C6 C7 C8 120.9(5) . . ?
C15 C16 C17 118.7(5) . . ?
O2 C1 O1 124.0(5) . . ?
O2 C1 C2 119.5(5) . . ?
O1 C1 C2 116.4(5) . . ?
N2 C15 C16 123.2(5) . . ?
C13 C17 C16 118.9(5) . . ?
N4 C28 C29 122.4(5) . . ?
C19 C20 C21 121.2(5) . . ?
C5 C10 C9 120.4(5) . . ?
C5 C10 C11 121.8(5) . . ?
C9 C10 C11 117.8(5) . . ?
N4 C27 C26 122.5(5) . . ?
N2 C14 C13 122.0(5) . . ?
C30 C26 C27 119.2(5) . . ?
C30 C26 N3 123.7(5) . . ?
C27 C26 N3 117.1(4) . . ?
C9 C8 C7 119.8(5) . . ?
C26 C30 C29 118.2(5) . . ?
C6 O6 C12 117.3(4) . . ?
C21 C22 C23 120.7(5) . . ?
C7 C6 O6 125.5(5) . . ?
C7 C6 C5 121.3(5) . . ?
O6 C6 C5 113.2(5) . . ?
C22 C21 C20 119.3(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O9 H9A O10A 0.82 1.93 2.751(9) 176.6 .
O10A H10A O2 0.85 1.94 2.778(5) 167.1 .

####################################################################### 
# 
# 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_ad4_2019
_database_code_depnum_ccdc_archive 'CCDC 1946385'
loop_
_audit_author_name
_audit_author_address
'Anna Dolega'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-08-09 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;

_audit_creation_date             2019-08-08T12:28:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_sum            'C28 H30 Cu N4 O6'
_chemical_formula_weight         582.1

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2180(5)
_cell_length_b                   8.5732(6)
_cell_length_c                   10.1631(9)
_cell_angle_alpha                100.133(6)
_cell_angle_beta                 110.494(6)
_cell_angle_gamma                98.773(5)
_cell_volume                     642.21(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5556
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      29.47

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

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             303
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 -3 0.045
0 0 -1 0.052
1 -4 1 0.101
-1 4 2 0.111
0 -1 0 0.093
-5 -1 3 0.113
2 0 -1 0.091
0 1 0 0.096
-2 4 1 0.138
-2 0 1 0.111
0 0 1 0.038


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

_exptl_absorpt_coefficient_mu    0.902
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
        Structure Analysis", published in
        F. R. Ahmed (Editor), "Crystallographic Computing",
        Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.8399
_exptl_absorpt_correction_T_max  0.9331

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

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_number            4837
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.229
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.976
_reflns_Friedel_coverage         0
_reflns_number_total             2469
_reflns_number_gt                2228
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       
;
        X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
        X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
        X-Area Integrate 1.72.0.0 (STOE, 2018)
        X-Area X-Red32 1.63.4.0 (STOE, 2017)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image
processing, for the correction and scaling of reflection intensities and
        for outlier rejection, version 1.81, Darmstadt 2018
;

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

_atom_sites_solution_hydrogens   mixed

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0488P)²+0.3110P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2469
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0829
_refine_ls_wR_factor_gt          0.0807
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.063

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5 0.5 0.5 0.01362(12) Uani 1 2 d S . P . .
O1 O 0.60289(18) 0.33104(16) 0.44003(15) 0.0154(3) Uani 1 1 d . . . . .
O2 O 0.7433(2) 0.15838(17) 0.29015(16) 0.0214(3) Uani 1 1 d . . . . .
N1 N 0.3368(2) 0.34413(19) 0.54811(17) 0.0140(3) Uani 1 1 d . . . . .
O3 O 0.7303(2) 0.5899(2) 0.81884(18) 0.0302(4) Uani 1 1 d . . . . .
H3A H 0.615(5) 0.551(4) 0.797(4) 0.060(10) Uiso 1 1 d . . . . .
N2 N 0.3717(2) 0.4811(2) 0.77935(18) 0.0178(4) Uani 1 1 d . . . . .
C9 C 0.2561(3) 0.4008(2) 0.6452(2) 0.0144(4) Uani 1 1 d . . . . .
C2 C 0.3587(3) 0.1061(2) 0.3897(2) 0.0143(4) Uani 1 1 d . . . . .
C1 C 0.5166(3) 0.1804(2) 0.3780(2) 0.0143(4) Uani 1 1 d . . . . .
C6 C 0.5860(3) 0.0803(2) 0.2917(2) 0.0162(4) Uani 1 1 d . . . . .
C5 C 0.4983(3) -0.0786(2) 0.2202(2) 0.0195(4) Uani 1 1 d . . . . .
H5 H 0.5453 -0.1413 0.1617 0.023 Uiso 1 1 calc R U . . .
C10 C 0.0719(3) 0.3757(2) 0.6018(2) 0.0161(4) Uani 1 1 d . . . . .
H10 H -0.0057 0.3175 0.5059 0.019 Uiso 1 1 calc R U . . .
C11 C 0.0044(3) 0.4375(2) 0.7017(2) 0.0186(4) Uani 1 1 d . . . . .
H11 H -0.1208 0.4236 0.6753 0.022 Uiso 1 1 calc R U . . .
C3 C 0.2732(3) -0.0604(2) 0.3176(2) 0.0185(4) Uani 1 1 d . . . . .
H3 H 0.1688 -0.1096 0.3288 0.022 Uiso 1 1 calc R U . . .
C8 C 0.2855(3) 0.1898(2) 0.4826(2) 0.0142(4) Uani 1 1 d . . . . .
H8 H 0.191 0.1269 0.4976 0.017 Uiso 1 1 calc R U . . .
C12 C 0.1223(3) 0.5200(3) 0.8409(2) 0.0198(4) Uani 1 1 d . . . . .
H12 H 0.0794 0.5627 0.9119 0.024 Uiso 1 1 calc R U . . .
C13 C 0.3030(3) 0.5391(3) 0.8746(2) 0.0200(4) Uani 1 1 d . . . . .
H13 H 0.383 0.5962 0.9701 0.024 Uiso 1 1 calc R U . . .
C4 C 0.3399(3) -0.1498(2) 0.2324(2) 0.0208(4) Uani 1 1 d . . . . .
H4 H 0.2798 -0.2594 0.1817 0.025 Uiso 1 1 calc R U . . .
C7 C 0.8151(3) 0.0709(3) 0.1995(3) 0.0284(5) Uani 1 1 d . . . . .
H7A H 0.7296 0.0424 0.0986 0.043 Uiso 1 1 calc R U . . .
H7B H 0.8378 -0.0288 0.2297 0.043 Uiso 1 1 calc R U . . .
H7C H 0.9273 0.139 0.208 0.043 Uiso 1 1 calc R U . . .
C14 C 0.7896(3) 0.7426(3) 0.9230(3) 0.0284(5) Uani 1 1 d . . . . .
H14A H 0.7219 0.8194 0.8824 0.043 Uiso 1 1 calc R U . . .
H14B H 0.917 0.7856 0.9479 0.043 Uiso 1 1 calc R U . . .
H14C H 0.7706 0.7279 1.0105 0.043 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.8995(13) 2_666 ?
Cu1 O1 1.8996(13) . ?
Cu1 N1 1.9913(17) 2_666 ?
Cu1 N1 1.9913(17) . ?
O1 C1 1.300(2) . ?
O2 C6 1.369(3) . ?
O2 C7 1.425(2) . ?
N1 C8 1.302(2) . ?
N1 C9 1.428(2) . ?
O3 C14 1.425(3) . ?
N2 C9 1.341(3) . ?
N2 C13 1.343(3) . ?
C9 C10 1.389(3) . ?
C2 C1 1.410(3) . ?
C2 C3 1.426(3) . ?
C2 C8 1.434(3) . ?
C1 C6 1.437(3) . ?
C6 C5 1.374(3) . ?
C5 C4 1.407(3) . ?
C10 C11 1.384(3) . ?
C11 C12 1.386(3) . ?
C3 C4 1.365(3) . ?
C12 C13 1.378(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
O1 Cu1 O1 180 2_666 . ?
O1 Cu1 N1 91.06(6) 2_666 2_666 ?
O1 Cu1 N1 88.94(6) . 2_666 ?
O1 Cu1 N1 88.94(6) 2_666 . ?
O1 Cu1 N1 91.06(6) . . ?
N1 Cu1 N1 180 2_666 . ?
C1 O1 Cu1 124.60(12) . . ?
C6 O2 C7 117.12(16) . . ?
C8 N1 C9 117.08(17) . . ?
C8 N1 Cu1 121.83(13) . . ?
C9 N1 Cu1 120.75(12) . . ?
C9 N2 C13 117.22(18) . . ?
N2 C9 C10 123.32(18) . . ?
N2 C9 N1 114.73(17) . . ?
C10 C9 N1 121.94(17) . . ?
C1 C2 C3 120.69(18) . . ?
C1 C2 C8 121.75(17) . . ?
C3 C2 C8 117.39(18) . . ?
O1 C1 C2 124.67(17) . . ?
O1 C1 C6 118.47(18) . . ?
C2 C1 C6 116.86(17) . . ?
O2 C6 C5 125.17(18) . . ?
O2 C6 C1 113.62(17) . . ?
C5 C6 C1 121.21(19) . . ?
C6 C5 C4 120.92(18) . . ?
C11 C10 C9 118.37(18) . . ?
C10 C11 C12 118.91(19) . . ?
C4 C3 C2 120.6(2) . . ?
N1 C8 C2 125.99(18) . . ?
C13 C12 C11 118.79(19) . . ?
N2 C13 C12 123.39(19) . . ?
C3 C4 C5 119.63(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
O3 H3A N2 0.89(4) 1.93(4) 2.814(3) 172(3) .

