# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_cuopcudapoh_4
_database_code_depnum_ccdc_archive 'CCDC 1954966'
loop_
_audit_author_name
_audit_author_address
'Marcos Antonio marcos.a.ribeiro'
;Universidade Federal Espirito Santo
Brazil
;
_audit_update_record             
;
2020-01-07 deposited with the CCDC.	2020-01-13 downloaded from the CCDC.
;
_audit_creation_date             2019-11-05
_audit_creation_method           
;
Olex2 1.3
(compiled Sep 10 2019 10:50:26 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H16 Cu2 N4 O8, 1.5(H2 O)'
_chemical_formula_sum            'C13 H19 Cu2 N4 O9.50'
_chemical_formula_weight         510.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.475(5)
_cell_length_b                   6.751(5)
_cell_length_c                   25.546(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.423(5)
_cell_angle_gamma                90
_cell_volume                     3448(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6110
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      66.0807
_cell_measurement_theta_min      3.7143
_shelx_estimated_absorpt_T_max   0.611
_shelx_estimated_absorpt_T_min   0.515
_exptl_absorpt_coefficient_mu    3.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.967
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2072
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            17648
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.185
_diffrn_reflns_theta_max         66.185
_diffrn_reflns_theta_min         3.717
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector_area_resol_mean 10.4186
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      .
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0051367000
_diffrn_orient_matrix_UB_12      -0.0168757000
_diffrn_orient_matrix_UB_13      -0.0584600000
_diffrn_orient_matrix_UB_21      0.0758238000
_diffrn_orient_matrix_UB_22      0.0390983000
_diffrn_orient_matrix_UB_23      0.0264978000
_diffrn_orient_matrix_UB_31      0.0128365000
_diffrn_orient_matrix_UB_32      -0.2240420000
_diffrn_orient_matrix_UB_33      0.0089968000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2515
_reflns_number_total             2990
_reflns_odcompleteness_completeness 97.09
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54)'
_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54)'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         2990
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0569P)²+2.5375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0987
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H,H,H,H,H) groups
2. Restrained distances
 HW1A-OW1
 0.85 with sigma of 0.02
 OW1-HW1B
 0.85 with sigma of 0.02
 HW2-OW2
 0.85 with sigma of 0.02
 H7A-O7
 0.85 with sigma of 0.02
 HW1B-HW1A
 1.55 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C12(H12)
3.b Secondary CH2 refined with riding coordinates:
 N4(H4A,H4B), C11(H11A,H11B), N3(H3A,H3B), C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C6(H6), C9(H9), C7(H7)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.53807(2) 0.30257(6) 0.54415(2) 0.02149(15) Uani 1 1 d . . . . .
O1 O 0.62409(11) 0.3401(3) 0.53319(9) 0.0231(4) Uani 1 1 d . . . . .
N2 N 0.44797(13) 0.2477(4) 0.53733(11) 0.0226(5) Uani 1 1 d . . . . .
O2 O 0.55342(11) 0.3502(3) 0.62354(9) 0.0250(5) Uani 1 1 d . . . . .
N1 N 0.50330(12) 0.2446(4) 0.46477(10) 0.0215(5) Uani 1 1 d . . . . .
C3 C 0.50121(17) 0.3076(4) 0.63488(13) 0.0242(6) Uani 1 1 d . . . . .
C10 C 0.40436(16) 0.1942(4) 0.48309(13) 0.0219(6) Uani 1 1 d . . . . .
C1 C 0.61776(15) 0.2973(4) 0.48325(13) 0.0219(6) Uani 1 1 d . . . . .
C2 C 0.54775(15) 0.2431(4) 0.44104(12) 0.0214(6) Uani 1 1 d . . . . .
C5 C 0.43517(16) 0.1894(4) 0.44238(13) 0.0229(6) Uani 1 1 d . . . . .
C4 C 0.43581(16) 0.2566(4) 0.58426(13) 0.0230(6) Uani 1 1 d . . . . .
O3 O 0.66415(11) 0.2907(3) 0.46484(9) 0.0255(5) Uani 1 1 d . . . . .
O4 O 0.54212(11) 0.2024(3) 0.39127(9) 0.0247(5) Uani 1 1 d . . . . .
O6 O 0.38235(11) 0.2283(3) 0.59187(9) 0.0268(5) Uani 1 1 d . . . . .
O5 O 0.49908(12) 0.3039(3) 0.68217(9) 0.0276(5) Uani 1 1 d . . . . .
C8 C 0.30114(16) 0.0877(4) 0.41172(14) 0.0269(7) Uani 1 1 d . . . . .
H8 H 0.2553 0.0521 0.4009 0.032 Uiso 1 1 calc R U . . .
C6 C 0.39864(16) 0.1328(5) 0.38739(13) 0.0263(7) Uani 1 1 d . . . . .
H6 H 0.4193 0.1295 0.3603 0.032 Uiso 1 1 calc R U . . .
C9 C 0.33656(16) 0.1455(4) 0.46698(14) 0.0252(6) Uani 1 1 d . . . . .
H9 H 0.3150 0.1519 0.4934 0.030 Uiso 1 1 calc R U . . .
C7 C 0.33150(16) 0.0809(5) 0.37216(14) 0.0284(7) Uani 1 1 d . . . . .
H7 H 0.3065 0.0410 0.3347 0.034 Uiso 1 1 calc R U . . .
Cu2 Cu 0.63274(2) 0.17767(6) 0.38631(2) 0.02338(16) Uani 1 1 d . . . . .
N4 N 0.58973(13) 0.0546(4) 0.31075(10) 0.0235(5) Uani 1 1 d . . . . .
H4A H 0.5732 -0.0649 0.3158 0.028 Uiso 1 1 calc R U . . .
H4B H 0.5541 0.1315 0.2909 0.028 Uiso 1 1 calc R U . . .
C11 C 0.74558(16) 0.0645(5) 0.35097(13) 0.0259(6) Uani 1 1 d . . . . .
H11A H 0.7913 0.0089 0.3631 0.031 Uiso 1 1 calc R U . . .
H11B H 0.7461 0.1965 0.3342 0.031 Uiso 1 1 calc R U . . .
N3 N 0.72537(13) 0.0851(4) 0.40019(11) 0.0260(6) Uani 1 1 d . . . . .
H3A H 0.7542 0.1710 0.4247 0.031 Uiso 1 1 calc R U . . .
H3B H 0.7308 -0.0346 0.4176 0.031 Uiso 1 1 calc R U . . .
C12 C 0.69735(15) -0.0705(5) 0.30726(12) 0.0238(6) Uani 1 1 d . . . . .
H12 H 0.6905 -0.1934 0.3264 0.029 Uiso 1 1 calc R U . . .
C13 C 0.62931(16) 0.0219(5) 0.27500(13) 0.0251(6) Uani 1 1 d . . . . .
H13A H 0.6359 0.1503 0.2590 0.030 Uiso 1 1 calc R U . . .
H13B H 0.6040 -0.0660 0.2434 0.030 Uiso 1 1 calc R U . . .
O7 O 0.72812(11) -0.1238(3) 0.26808(9) 0.0281(5) Uani 1 1 d D . . . .
OW1 O 0.64172(11) 0.4693(3) 0.34445(10) 0.0274(5) Uani 1 1 d D . . . .
OW3 O 0.65308(13) 0.4620(4) 0.72974(11) 0.0294(5) Uani 1 1 d . . . . .
OW2 O 0.5000 0.3749(5) 0.2500 0.0327(7) Uani 1 2 d DS T P . .
HW3A H 0.679(3) 0.534(8) 0.722(2) 0.049 Uiso 1 1 d . U . . .
HW3B H 0.622(3) 0.447(7) 0.700(2) 0.049 Uiso 1 1 d . U . . .
HW1A H 0.630(2) 0.465(6) 0.3082(8) 0.049 Uiso 1 1 d D U . . .
HW1B H 0.632(2) 0.567(5) 0.3617(15) 0.049 Uiso 1 1 d D U . . .
HW2 H 0.497(2) 0.463(5) 0.2727(16) 0.049 Uiso 1 1 d D U . . .
H7A H 0.711(2) -0.232(4) 0.2539(19) 0.049 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.983(2) . ?
Cu1 N2 1.914(3) . ?
Cu1 O2 1.959(2) . ?
Cu1 N1 1.928(3) . ?
O1 C1 1.266(4) . ?
N2 C10 1.407(4) . ?
N2 C4 1.318(4) . ?
O2 C3 1.289(4) . ?
N1 C2 1.305(4) . ?
N1 C5 1.413(4) . ?
C3 C4 1.561(5) . ?
C3 O5 1.226(4) . ?
C10 C5 1.422(4) . ?
C10 C9 1.400(5) . ?
C1 C2 1.540(4) . ?
C1 O3 1.248(4) . ?
C2 O4 1.263(4) . ?
C5 C6 1.389(5) . ?
C4 O6 1.247(4) . ?
O3 Cu2 2.018(2) . ?
O4 Cu2 2.003(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.393(5) . ?
C8 C7 1.389(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.394(5) . ?
C9 H9 0.9500 . ?
C7 H7 0.9500 . ?
Cu2 N4 1.991(3) . ?
Cu2 N3 1.989(3) . ?
Cu2 OW1 2.282(3) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N4 C13 1.474(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 N3 1.479(4) . ?
C11 C12 1.519(4) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
C12 H12 1.0000 . ?
C12 C13 1.525(5) . ?
C12 O7 1.432(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
O7 H7A 0.84(2) . ?
OW1 HW1A 0.867(18) . ?
OW1 HW1B 0.863(18) . ?
OW3 HW3A 0.82(6) . ?
OW3 HW3B 0.81(6) . ?
OW2 HW2 0.849(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 O1 167.03(10) . . ?
N2 Cu1 O2 84.73(10) . . ?
N2 Cu1 N1 82.80(11) . . ?
O2 Cu1 O1 108.18(9) . . ?
N1 Cu1 O1 84.28(10) . . ?
N1 Cu1 O2 167.54(10) . . ?
C1 O1 Cu1 110.50(19) . . ?
C10 N2 Cu1 115.2(2) . . ?
C4 N2 Cu1 116.0(2) . . ?
C4 N2 C10 128.7(3) . . ?
C3 O2 Cu1 111.40(19) . . ?
C2 N1 Cu1 115.0(2) . . ?
C2 N1 C5 129.4(3) . . ?
C5 N1 Cu1 115.2(2) . . ?
O2 C3 C4 117.1(3) . . ?
O5 C3 O2 125.1(3) . . ?
O5 C3 C4 117.8(3) . . ?
N2 C10 C5 114.0(3) . . ?
C9 C10 N2 126.6(3) . . ?
C9 C10 C5 119.4(3) . . ?
O1 C1 C2 118.5(3) . . ?
O3 C1 O1 125.5(3) . . ?
O3 C1 C2 115.9(3) . . ?
N1 C2 C1 111.4(3) . . ?
O4 C2 N1 130.7(3) . . ?
O4 C2 C1 117.8(3) . . ?
N1 C5 C10 112.8(3) . . ?
C6 C5 N1 126.9(3) . . ?
C6 C5 C10 120.3(3) . . ?
N2 C4 C3 110.3(3) . . ?
O6 C4 N2 129.4(3) . . ?
O6 C4 C3 120.4(3) . . ?
C1 O3 Cu2 111.41(19) . . ?
C2 O4 Cu2 110.13(19) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.3(3) . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.7(3) . . ?
C7 C6 H6 120.1 . . ?
C10 C9 H9 120.4 . . ?
C8 C9 C10 119.2(3) . . ?
C8 C9 H9 120.4 . . ?
C8 C7 C6 120.1(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
O3 Cu2 OW1 94.87(9) . . ?
O4 Cu2 O3 83.41(9) . . ?
O4 Cu2 OW1 102.02(8) . . ?
N4 Cu2 O3 171.64(10) . . ?
N4 Cu2 O4 88.79(10) . . ?
N4 Cu2 OW1 89.68(10) . . ?
N3 Cu2 O3 89.54(10) . . ?
N3 Cu2 O4 161.14(10) . . ?
N3 Cu2 N4 96.97(11) . . ?
N3 Cu2 OW1 95.98(10) . . ?
Cu2 N4 H4A 107.4 . . ?
Cu2 N4 H4B 107.4 . . ?
H4A N4 H4B 106.9 . . ?
C13 N4 Cu2 119.7(2) . . ?
C13 N4 H4A 107.4 . . ?
C13 N4 H4B 107.4 . . ?
H11A C11 H11B 108.1 . . ?
N3 C11 H11A 109.6 . . ?
N3 C11 H11B 109.6 . . ?
N3 C11 C12 110.4(2) . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
Cu2 N3 H3A 107.9 . . ?
Cu2 N3 H3B 107.9 . . ?
C11 N3 Cu2 117.6(2) . . ?
C11 N3 H3A 107.9 . . ?
C11 N3 H3B 107.9 . . ?
H3A N3 H3B 107.2 . . ?
C11 C12 H12 108.7 . . ?
C11 C12 C13 114.4(3) . . ?
C13 C12 H12 108.7 . . ?
O7 C12 C11 107.4(2) . . ?
O7 C12 H12 108.7 . . ?
O7 C12 C13 108.7(2) . . ?
N4 C13 C12 112.5(2) . . ?
N4 C13 H13A 109.1 . . ?
N4 C13 H13B 109.1 . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C12 O7 H7A 106(3) . . ?
Cu2 OW1 HW1A 115(3) . . ?
Cu2 OW1 HW1B 110(3) . . ?
HW1A OW1 HW1B 123(3) . . ?
HW3A OW3 HW3B 105(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
N4 H4B OW2 0.91 2.06 2.935(4) 160.0 .
OW3 HW3A O7 0.82(6) 2.01(6) 2.757(4) 153(5) 7_656
OW3 HW3B O2 0.81(6) 2.08(6) 2.876(3) 167(5) .
OW1 HW1B O6 0.863(18) 1.916(18) 2.774(3) 173(4) 5_666
OW2 HW2 O5 0.849(19) 1.94(2) 2.771(4) 168(5) 5_666
O7 H7A OW3 0.84(2) 1.94(2) 2.760(4) 164(5) 6

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 C2 4.5(3) . . . . ?
Cu1 O1 C1 O3 -173.8(2) . . . . ?
Cu1 N2 C10 C5 0.2(3) . . . . ?
Cu1 N2 C10 C9 179.5(2) . . . . ?
Cu1 N2 C4 C3 -1.1(3) . . . . ?
Cu1 N2 C4 O6 179.9(3) . . . . ?
Cu1 O2 C3 C4 -7.8(3) . . . . ?
Cu1 O2 C3 O5 172.1(2) . . . . ?
Cu1 N1 C2 C1 -2.2(3) . . . . ?
Cu1 N1 C2 O4 176.4(3) . . . . ?
Cu1 N1 C5 C10 2.1(3) . . . . ?
Cu1 N1 C5 C6 -177.3(2) . . . . ?
O1 C1 C2 N1 -1.8(4) . . . . ?
O1 C1 C2 O4 179.4(2) . . . . ?
O1 C1 O3 Cu2 171.7(2) . . . . ?
N2 C10 C5 N1 -1.5(3) . . . . ?
N2 C10 C5 C6 178.0(3) . . . . ?
N2 C10 C9 C8 -177.3(3) . . . . ?
O2 C3 C4 N2 6.2(4) . . . . ?
O2 C3 C4 O6 -174.7(3) . . . . ?
N1 C2 O4 Cu2 -169.0(3) . . . . ?
N1 C5 C6 C7 179.5(3) . . . . ?
C10 N2 C4 C3 175.6(3) . . . . ?
C10 N2 C4 O6 -3.4(5) . . . . ?
C10 C5 C6 C7 0.1(4) . . . . ?
C1 C2 O4 Cu2 9.6(3) . . . . ?
C2 N1 C5 C10 174.5(3) . . . . ?
C2 N1 C5 C6 -4.9(5) . . . . ?
C2 C1 O3 Cu2 -6.7(3) . . . . ?
C5 N1 C2 C1 -174.6(3) . . . . ?
C5 N1 C2 O4 4.0(5) . . . . ?
C5 C10 C9 C8 1.9(4) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
C4 N2 C10 C5 -176.5(3) . . . . ?
C4 N2 C10 C9 2.8(5) . . . . ?
O3 C1 C2 N1 176.8(2) . . . . ?
O3 C1 C2 O4 -2.0(4) . . . . ?
O5 C3 C4 N2 -173.7(3) . . . . ?
O5 C3 C4 O6 5.3(4) . . . . ?
C9 C10 C5 N1 179.2(2) . . . . ?
C9 C10 C5 C6 -1.3(4) . . . . ?
C9 C8 C7 C6 0.0(5) . . . . ?
C7 C8 C9 C10 -1.2(4) . . . . ?
Cu2 N4 C13 C12 46.2(3) . . . . ?
C11 C12 C13 N4 -68.3(3) . . . . ?
N3 C11 C12 C13 73.4(3) . . . . ?
N3 C11 C12 O7 -165.8(2) . . . . ?
C12 C11 N3 Cu2 -55.3(3) . . . . ?
O7 C12 C13 N4 171.6(2) . . . . ?

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

data_cudap_03
_database_code_depnum_ccdc_archive 'CCDC 1954967'
loop_
_audit_author_name
_audit_author_address
'Marcos Antonio marcos.a.ribeiro'
;Universidade Federal Espirito Santo
Brazil
;
_audit_update_record             
;
2020-01-07 deposited with the CCDC.	2020-01-13 downloaded from the CCDC.
;
_audit_creation_date             2019-09-20
_audit_creation_method           
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H16 Cu2 N4 O7, H2 O'
_chemical_formula_sum            'C13 H18 Cu2 N4 O8'
_chemical_formula_weight         485.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H18 Cu2 N4 O8'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9426(5)
_cell_length_b                   10.4944(7)
_cell_length_c                   11.9846(8)
_cell_angle_alpha                76.242(5)
_cell_angle_beta                 88.366(6)
_cell_angle_gamma                73.715(6)
_cell_volume                     813.42(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2059
_cell_measurement_temperature    270.05(10)
_cell_measurement_theta_max      29.3595
_cell_measurement_theta_min      2.0757
_shelx_estimated_absorpt_T_max   0.879
_shelx_estimated_absorpt_T_min   0.345
_exptl_absorpt_coefficient_mu    2.670
_exptl_absorpt_correction_T_max  0.875
_exptl_absorpt_correction_T_min  0.389
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.982
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.5063
_exptl_crystal_size_mid          0.358
_exptl_crystal_size_min          0.0496
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5904
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.082
_diffrn_ambient_temperature      270.05(10)
_diffrn_detector_area_resol_mean 10.4186
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -37.00   57.00   1.0000    3.5300
omega____ theta____ kappa____ phi______ frames
    -      -10.7980   77.0000 -150.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega   -9.00   92.00   1.0000    3.5300
omega____ theta____ kappa____ phi______ frames
    -       12.8293   77.0000  120.0000 101

#__ type_ start__ end____ width___ exp.time_
  3 omega  -21.00   79.00   1.0000    3.5300
omega____ theta____ kappa____ phi______ frames
    -       12.8293   77.0000    0.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0478911000
_diffrn_orient_matrix_UB_12      -0.0701067000
_diffrn_orient_matrix_UB_13      0.0036522000
_diffrn_orient_matrix_UB_21      0.0081041000
_diffrn_orient_matrix_UB_22      -0.0122674000
_diffrn_orient_matrix_UB_23      0.0606656000
_diffrn_orient_matrix_UB_31      -0.0946935000
_diffrn_orient_matrix_UB_32      -0.0134999000
_diffrn_orient_matrix_UB_33      0.0042134000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2648
_reflns_number_total             3333
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3333
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0341P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0866
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups, All O(H,H,H,H) groups
2. Restrained distances
 OW1-HW1A = OW1-HW1B
 0.85 with sigma of 0.01
 OW2-HW2B = OW2-HW2A
 0.85 with sigma of 0.01
 HW1B-HW1A
 1.4 with sigma of 0.01
 HW2A-HW2B
 1.4 with sigma of 0.01
3.a Free rotating group:
 OW2(HW2A,HW2B,HW1A,HW1B)
3.b Secondary CH2 refined with riding coordinates:
 N4(H4A,H4B), N3(H3A,H3B), C13(H13A,H13B), C11(H11A,H11B), C12(H12A,H12B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.16006(6) 0.07600(4) 0.89997(3) 0.02007(13) Uani 1 1 d . . . . .
Cu2 Cu 0.14727(6) 0.29021(4) 1.25079(3) 0.02238(13) Uani 1 1 d . . . . .
O1 O 0.0278(3) 0.2515(2) 0.94087(19) 0.0227(5) Uani 1 1 d . . . . .
O4 O 0.2235(3) 0.1003(2) 1.22382(19) 0.0225(5) Uani 1 1 d . . . . .
N1 N 0.2390(4) 0.0126(3) 1.0610(2) 0.0173(6) Uani 1 1 d . . . . .
O3 O 0.0171(3) 0.3405(2) 1.0931(2) 0.0252(6) Uani 1 1 d . . . . .
O2 O 0.1155(4) 0.0985(2) 0.73470(19) 0.0256(6) Uani 1 1 d . . . . .
O6 O 0.4111(3) -0.2450(2) 0.7708(2) 0.0255(6) Uani 1 1 d . . . . .
N2 N 0.3070(4) -0.1056(3) 0.8974(2) 0.0205(6) Uani 1 1 d . . . . .
C2 C 0.1869(5) 0.1055(3) 1.1199(3) 0.0187(7) Uani 1 1 d . . . . .
O5 O 0.2298(4) -0.0148(3) 0.6000(2) 0.0378(7) Uani 1 1 d . . . . .
C6 C 0.4487(5) -0.1914(3) 1.2023(3) 0.0231(8) Uani 1 1 d . . . . .
H6 H 0.4275 -0.1476 1.2624 0.028 Uiso 1 1 calc R . . . .
C1 C 0.0670(5) 0.2439(3) 1.0445(3) 0.0196(7) Uani 1 1 d . . . . .
C10 C 0.3970(5) -0.1899(3) 1.0030(3) 0.0175(7) Uani 1 1 d . . . . .
C5 C 0.3637(5) -0.1237(3) 1.0947(3) 0.0184(7) Uani 1 1 d . . . . .
C4 C 0.3231(5) -0.1352(3) 0.7955(3) 0.0207(7) Uani 1 1 d . . . . .
C7 C 0.5669(5) -0.3261(3) 1.2203(3) 0.0270(8) Uani 1 1 d . . . . .
H7 H 0.6260 -0.3724 1.2927 0.032 Uiso 1 1 calc R . . . .
C8 C 0.5973(5) -0.3917(3) 1.1313(3) 0.0256(8) Uani 1 1 d . . . . .
H8 H 0.6754 -0.4822 1.1446 0.031 Uiso 1 1 calc R . . . .
C9 C 0.5128(5) -0.3242(3) 1.0231(3) 0.0237(8) Uani 1 1 d . . . . .
H9 H 0.5338 -0.3692 0.9638 0.028 Uiso 1 1 calc R . . . .
C3 C 0.2132(5) -0.0074(4) 0.7012(3) 0.0259(8) Uani 1 1 d . . . . .
N4 N 0.2925(4) 0.2201(3) 1.4033(2) 0.0238(7) Uani 1 1 d . . . . .
H4A H 0.2550 0.1391 1.4428 0.029 Uiso 1 1 calc R . . . .
H4B H 0.4351 0.1915 1.3904 0.029 Uiso 1 1 calc R . . . .
N3 N 0.1799(4) 0.4774(3) 1.2253(2) 0.0247(7) Uani 1 1 d . . . . .
H3A H 0.3133 0.4749 1.1977 0.030 Uiso 1 1 calc R . . . .
H3B H 0.0841 0.5377 1.1649 0.030 Uiso 1 1 calc R . . . .
C13 C 0.2610(6) 0.3134(4) 1.4815(3) 0.0292(9) Uani 1 1 d . . . . .
H13A H 0.3508 0.2700 1.5487 0.035 Uiso 1 1 calc R . . . .
H13B H 0.1243 0.3295 1.5070 0.035 Uiso 1 1 calc R . . . .
C11 C 0.1526(5) 0.5374(3) 1.3268(3) 0.0294(9) Uani 1 1 d . . . . .
H11A H 0.0160 0.5477 1.3516 0.035 Uiso 1 1 calc R . . . .
H11B H 0.1736 0.6275 1.3056 0.035 Uiso 1 1 calc R . . . .
C12 C 0.2977(5) 0.4485(4) 1.4251(3) 0.0299(9) Uani 1 1 d . . . . .
H12A H 0.4325 0.4309 1.3967 0.036 Uiso 1 1 calc R . . . .
H12B H 0.2927 0.4996 1.4833 0.036 Uiso 1 1 calc R . . . .
OW1 O -0.1509(4) 0.3370(3) 1.3330(2) 0.0298(6) Uani 1 1 d D . . . .
OW2 O -0.2064(4) 0.1906(3) 1.5468(2) 0.0435(7) Uani 1 1 d D . . . .
HW2A H -0.1165 0.1666 1.5964 0.052 Uiso 1 1 d DG . . . .
HW2B H -0.2021 0.1295 1.5126 0.052 Uiso 1 1 d DG . . . .
HW1A H -0.2259 0.3055 1.2991 0.052 Uiso 1 1 d DG . . . .
HW1B H -0.1619 0.3017 1.4040 0.052 Uiso 1 1 d DG . . . .


_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 1.982(2) . ?
Cu1 N1 1.927(3) . ?
Cu1 O2 1.961(2) . ?
Cu1 N2 1.900(3) . ?
Cu2 O4 2.016(2) . ?
Cu2 O3 2.006(2) . ?
Cu2 N4 1.986(3) . ?
Cu2 N3 1.991(3) . ?
Cu2 OW1 2.245(2) . ?
O1 C1 1.259(4) . ?
O4 C2 1.263(4) . ?
N1 C2 1.302(4) . ?
N1 C5 1.418(4) . ?
O3 C1 1.248(4) . ?
O2 C3 1.277(4) . ?
O6 C4 1.243(4) . ?
N2 C10 1.406(4) . ?
N2 C4 1.324(4) . ?
C2 C1 1.536(5) . ?
O5 C3 1.233(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.374(5) . ?
C6 C7 1.390(4) . ?
C10 C5 1.416(4) . ?
C10 C9 1.380(4) . ?
C4 C3 1.553(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(5) . ?
C9 H9 0.9300 . ?
N4 H4A 0.9700 . ?
N4 H4B 0.9700 . ?
N4 C13 1.480(4) . ?
N3 H3A 0.9700 . ?
N3 H3B 0.9700 . ?
N3 C11 1.482(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.505(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.514(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
OW1 HW1A 0.8470 . ?
OW1 HW1B 0.8538 . ?
OW2 HW2A 0.8180 . ?
OW2 HW2B 0.8322 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 O1 84.03(10) . . ?
N1 Cu1 O2 166.96(10) . . ?
O2 Cu1 O1 109.00(9) . . ?
N2 Cu1 O1 166.63(11) . . ?
N2 Cu1 N1 82.62(11) . . ?
N2 Cu1 O2 84.35(10) . . ?
O4 Cu2 OW1 111.16(10) . . ?
O3 Cu2 O4 82.91(9) . . ?
O3 Cu2 OW1 92.22(9) . . ?
N4 Cu2 O4 90.78(10) . . ?
N4 Cu2 O3 173.49(10) . . ?
N4 Cu2 N3 95.17(11) . . ?
N4 Cu2 OW1 91.54(11) . . ?
N3 Cu2 O4 152.05(11) . . ?
N3 Cu2 O3 89.71(10) . . ?
N3 Cu2 OW1 95.98(10) . . ?
C1 O1 Cu1 110.7(2) . . ?
C2 O4 Cu2 110.2(2) . . ?
C2 N1 Cu1 115.0(2) . . ?
C2 N1 C5 129.5(3) . . ?
C5 N1 Cu1 115.1(2) . . ?
C1 O3 Cu2 112.0(2) . . ?
C3 O2 Cu1 111.8(2) . . ?
C10 N2 Cu1 115.9(2) . . ?
C4 N2 Cu1 116.3(2) . . ?
C4 N2 C10 127.6(3) . . ?
O4 C2 N1 131.1(3) . . ?
O4 C2 C1 117.4(3) . . ?
N1 C2 C1 111.5(3) . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C7 119.2(3) . . ?
C7 C6 H6 120.4 . . ?
O1 C1 C2 118.6(3) . . ?
O3 C1 O1 125.6(3) . . ?
O3 C1 C2 115.9(3) . . ?
N2 C10 C5 113.7(3) . . ?
C9 C10 N2 127.0(3) . . ?
C9 C10 C5 119.3(3) . . ?
C6 C5 N1 126.9(3) . . ?
C6 C5 C10 120.4(3) . . ?
C10 C5 N1 112.6(3) . . ?
O6 C4 N2 128.9(3) . . ?
O6 C4 C3 121.1(3) . . ?
N2 C4 C3 110.0(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.5(3) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 C10 120.0(3) . . ?
C8 C9 H9 120.0 . . ?
O2 C3 C4 117.1(3) . . ?
O5 C3 O2 125.0(3) . . ?
O5 C3 C4 117.9(3) . . ?
Cu2 N4 H4A 107.9 . . ?
Cu2 N4 H4B 107.9 . . ?
H4A N4 H4B 107.2 . . ?
C13 N4 Cu2 117.8(2) . . ?
C13 N4 H4A 107.9 . . ?
C13 N4 H4B 107.9 . . ?
Cu2 N3 H3A 108.3 . . ?
Cu2 N3 H3B 108.3 . . ?
H3A N3 H3B 107.4 . . ?
C11 N3 Cu2 115.9(2) . . ?
C11 N3 H3A 108.3 . . ?
C11 N3 H3B 108.3 . . ?
N4 C13 H13A 109.1 . . ?
N4 C13 H13B 109.1 . . ?
N4 C13 C12 112.5(3) . . ?
H13A C13 H13B 107.8 . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
N3 C11 H11A 109.4 . . ?
N3 C11 H11B 109.4 . . ?
N3 C11 C12 111.4(3) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C13 C12 C11 115.8(3) . . ?
C13 C12 H12A 108.3 . . ?
C13 C12 H12B 108.3 . . ?
C11 C12 H12A 108.3 . . ?
C11 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
Cu2 OW1 HW1A 105.9 . . ?
Cu2 OW1 HW1B 120.7 . . ?
HW1A OW1 HW1B 103.2 . . ?
HW2A OW2 HW2B 111.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 OW2 0.93 2.74 3.404(4) 129.5 2_558
C8 H8 OW1 0.93 2.64 3.344(4) 132.6 1_645
N4 H4A O5 0.97 2.21 3.099(4) 152.0 1_556
N4 H4B O6 0.97 2.21 2.907(4) 127.7 2_657
N4 H4B O5 0.97 2.52 3.416(4) 153.3 2_657
N3 H3B O1 0.97 2.20 3.051(4) 145.1 2_567
OW2 HW2A O2 0.82 2.19 3.007(4) 177.5 1_556
OW2 HW2A O5 0.82 2.61 3.165(4) 126.6 1_556
OW2 HW2B O5 0.83 2.06 2.873(4) 167.0 2_557
OW1 HW1A O6 0.85 1.88 2.724(3) 175.1 2_557
OW1 HW1B OW2 0.85 1.90 2.734(4) 165.6 .

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 14 7 0.1943 0.0000 14.0000 7.0000 -0.9559 0.2529 -0.1595
0 -14 -7 0.1883 -0.0000 -14.0000 -7.0000 0.9559 -0.2529 0.1595
9 0 -3 0.1803 9.0000 -0.0000 -3.0000 0.4201 -0.1091 -0.8649
-9 0 3 0.1533 -9.0000 0.0000 3.0000 -0.4201 0.1091 0.8649
1 0 -16 0.0248 1.0000 0.0000 -16.0000 -0.0105 -0.9625 -0.1621
-1 0 16 0.0248 -1.0000 -0.0000 16.0000 0.0105 0.9625 0.1621

_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_gilr1
_database_code_depnum_ccdc_archive 'CCDC 1954969'
loop_
_audit_author_name
_audit_author_address
'Marcos Antonio marcos.a.ribeiro'
;Universidade Federal Espirito Santo
Brazil
;
_audit_update_record             
;
2020-01-07 deposited with the CCDC.	2020-01-13 downloaded from the CCDC.
;
_audit_creation_date             2019-09-20
_audit_creation_method           
;
Olex2 1.2
(compiled May 29 2018 13:30:08 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H14 Cu2 N4 O7, 4(H2 O)'
_chemical_formula_sum            'C12 H22 Cu2 N4 O11'
_chemical_formula_weight         525.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H44 N8 O22 Cu4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.67460(10)
_cell_length_b                   17.3302(2)
_cell_length_c                   16.4950(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.1980(10)
_cell_angle_gamma                90
_cell_volume                     1906.61(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    31878
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      29.4160
_cell_measurement_theta_min      3.0450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.297
_exptl_absorpt_correction_T_max  0.790
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.830
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.1806
_exptl_crystal_size_mid          0.1515
_exptl_crystal_size_min          0.1108
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            53889
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.737
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -67.00    3.00   1.0000   27.5700
omega____ theta____ kappa____ phi______ frames
    -      -10.7717  123.0000  139.0000 70

#__ type_ start__ end____ width___ exp.time_
  2 omega  -57.00   17.00   1.0000   27.5700
omega____ theta____ kappa____ phi______ frames
    -      -10.7717  107.0000 -146.0000 74

#__ type_ start__ end____ width___ exp.time_
  3 omega  -88.00  -26.00   1.0000   27.5700
omega____ theta____ kappa____ phi______ frames
    -      -10.7717  154.0000    6.0000 62

#__ type_ start__ end____ width___ exp.time_
  4 omega  -21.00   85.00   1.0000   27.5700
omega____ theta____ kappa____ phi______ frames
    -       12.8029   77.0000   90.0000 106

#__ type_ start__ end____ width___ exp.time_
  5 omega   -2.00   89.00   1.0000   27.5700
omega____ theta____ kappa____ phi______ frames
    -       12.8029   38.0000   30.0000 91

#__ type_ start__ end____ width___ exp.time_
  6 omega  -14.00   89.00   1.0000   27.5700
omega____ theta____ kappa____ phi______ frames
    -       12.8029   38.0000  -60.0000 103

#__ type_ start__ end____ width___ exp.time_
  7 omega  -66.00   46.00   1.0000   27.5700
omega____ theta____ kappa____ phi______ frames
    -       12.8029  -77.0000    0.0000 112

#__ type_ start__ end____ width___ exp.time_
  8 omega  -87.00   16.00   1.0000   27.5700
omega____ theta____ kappa____ phi______ frames
    -      -10.7717  -38.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
  9 omega  -44.00   68.00   1.0000   27.5700
omega____ theta____ kappa____ phi______ frames
    -      -10.7717   77.0000  -30.0000 112

#__ type_ start__ end____ width___ exp.time_
 10 omega  -34.00   18.00   1.0000   27.5700
omega____ theta____ kappa____ phi______ frames
    -       12.8029  107.0000 -146.0000 52

#__ type_ start__ end____ width___ exp.time_
 11 omega   56.00  103.00   1.0000   27.5700
omega____ theta____ kappa____ phi______ frames
    -       12.8029  179.0000   30.0000 47

#__ type_ start__ end____ width___ exp.time_
 12 omega   56.00  103.00   1.0000   27.5700
omega____ theta____ kappa____ phi______ frames
    -       12.8029  179.0000  150.0000 47

#__ type_ start__ end____ width___ exp.time_
 13 omega  -14.00   89.00   1.0000   27.5700
omega____ theta____ kappa____ phi______ frames
    -       12.8029   38.0000   60.0000 103

#__ type_ start__ end____ width___ exp.time_
 14 omega  -14.00   52.00   1.0000   27.5700
omega____ theta____ kappa____ phi______ frames
    -       12.8029   38.0000  120.0000 66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0325717000
_diffrn_orient_matrix_UB_12      0.0382937000
_diffrn_orient_matrix_UB_13      -0.0078480000
_diffrn_orient_matrix_UB_21      -0.0272350000
_diffrn_orient_matrix_UB_22      -0.0104192000
_diffrn_orient_matrix_UB_23      -0.0404743000
_diffrn_orient_matrix_UB_31      -0.0973994000
_diffrn_orient_matrix_UB_32      -0.0098874000
_diffrn_orient_matrix_UB_33      0.0121835000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3473
_reflns_number_total             3898
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_refine_diff_density_max         0.436
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3898
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0186
_refine_ls_restrained_S_all      1.286
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0340P)²+0.4723P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0542
_refine_ls_wR_factor_ref         0.0548
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups, All O(H,H,H,H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O1W-H1WA
 0.85 with sigma of 0.001
 H4WA-H4WB
 1.34 with sigma of 0.02
 H4A-N4 = H4B-N4
 1 with sigma of 0.01
 H3A-N3 = H3B-N3
 1 with sigma of 0.01
 O1W-H1WB
 0.85 with sigma of 0.001
 O4W-H4WA = O4W-H4WB
 0.85 with sigma of 0.001
3.a Free rotating group:
 O3W(H3WA,H3WB), O5W(H5WA,H5WB), O2W(H2WA,H2WB), O4W(H1WB,H4A,H3A,H4B,H3B)
3.b Rotating group:
 O1W(H1WA)
3.c Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B)
3.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C7(H7), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.18225(3) 0.08323(2) 0.93935(2) 0.01244(6) Uani 1 1 d . . . . .
O2 O 0.13893(17) 0.11695(7) 0.82740(7) 0.0166(2) Uani 1 1 d . . . . .
O3 O 0.08784(16) 0.19350(6) 1.14275(7) 0.0162(2) Uani 1 1 d . . . . .
N1 N 0.22740(18) 0.02887(7) 1.03968(8) 0.0119(3) Uani 1 1 d . . . . .
O1 O 0.11066(16) 0.17139(6) 1.01004(7) 0.0147(2) Uani 1 1 d . . . . .
O4 O 0.21226(16) 0.05076(6) 1.17885(6) 0.0147(2) Uani 1 1 d . . . . .
C1 C 0.1264(2) 0.15115(9) 1.08295(10) 0.0134(3) Uani 1 1 d . . . . .
N2 N 0.24962(18) -0.01392(7) 0.89282(8) 0.0125(3) Uani 1 1 d . . . . .
C4 C 0.2347(2) -0.01745(9) 0.81316(9) 0.0129(3) Uani 1 1 d . . . . .
C3 C 0.1700(2) 0.06239(10) 0.77735(10) 0.0154(3) Uani 1 1 d . . . . .
C6 C 0.3461(2) -0.09815(9) 1.09426(10) 0.0148(3) Uani 1 1 d . . . . .
H6 H 0.3382 -0.0822 1.1492 0.018 Uiso 1 1 calc R . . . .
C2 C 0.1964(2) 0.06896(9) 1.10461(10) 0.0126(3) Uani 1 1 d . . . . .
C8 C 0.4207(2) -0.19606(9) 0.99535(10) 0.0158(3) Uani 1 1 d . . . . .
H8 H 0.4646 -0.2468 0.9836 0.019 Uiso 1 1 calc R . . . .
C10 C 0.3029(2) -0.07190(9) 0.94943(9) 0.0119(3) Uani 1 1 d . . . . .
C7 C 0.4120(2) -0.17213(9) 1.07557(10) 0.0162(3) Uani 1 1 d . . . . .
H7 H 0.4514 -0.2065 1.1181 0.019 Uiso 1 1 calc R . . . .
C5 C 0.2918(2) -0.04792(9) 1.03124(9) 0.0119(3) Uani 1 1 d . . . . .
C9 C 0.3658(2) -0.14640(9) 0.93216(10) 0.0139(3) Uani 1 1 d . . . . .
H9 H 0.3713 -0.1633 0.8775 0.017 Uiso 1 1 calc R . . . .
Cu2 Cu 0.12436(3) 0.13735(2) 1.24825(2) 0.01451(6) Uani 1 1 d . . . . .
N4 N 0.1367(2) 0.07448(8) 1.34870(8) 0.0185(3) Uani 1 1 d D . . . .
N3 N -0.0145(2) 0.21766(8) 1.31295(8) 0.0191(3) Uani 1 1 d D . . . .
C12 C 0.1025(3) 0.12767(11) 1.41731(10) 0.0252(4) Uani 1 1 d . . . . .
H12A H 0.2266 0.1568 1.4313 0.030 Uiso 1 1 calc R . . . .
H12B H 0.0644 0.0980 1.4656 0.030 Uiso 1 1 calc R . . . .
O5 O 0.15433(18) 0.06808(7) 0.70256(7) 0.0215(3) Uani 1 1 d . . . . .
O6 O 0.25940(17) -0.07279(7) 0.76626(7) 0.0181(2) Uani 1 1 d . . . . .
C11 C -0.0639(3) 0.18276(10) 1.39199(10) 0.0221(4) Uani 1 1 d . . . . .
H11A H -0.1930 0.1547 1.3866 0.027 Uiso 1 1 calc R . . . .
H11B H -0.0766 0.2236 1.4334 0.027 Uiso 1 1 calc R . . . .
O1W O 0.44384(17) 0.18008(7) 1.27534(7) 0.0190(2) Uani 1 1 d D . . . .
H1WA H 0.5320 0.1466 1.2565 0.023 Uiso 1 1 d DGR . . . .
O3W O -0.11453(18) 0.16530(7) 0.62504(8) 0.0251(3) Uani 1 1 d . . . . .
H3WA H -0.0290 0.1373 0.6532 0.038 Uiso 1 1 d G . . . .
H3WB H -0.0550 0.2096 0.6201 0.038 Uiso 1 1 d G . . . .
O5W O 0.44618(19) -0.02202(8) 0.61240(8) 0.0263(3) Uani 1 1 d . . . . .
H5WA H 0.4630 0.0229 0.5900 0.040 Uiso 1 1 d G . . . .
H5WB H 0.3638 -0.0133 0.6510 0.040 Uiso 1 1 d G . . . .
O2W O 0.5340(2) 0.31968(8) 1.21012(9) 0.0347(3) Uani 1 1 d . . . . .
H2WA H 0.4372 0.3436 1.1837 0.052 Uiso 1 1 d G . . . .
H2WB H 0.6385 0.3270 1.1811 0.052 Uiso 1 1 d G . . . .
O4W O 0.5667(2) 0.10486(8) 0.53025(9) 0.0339(3) Uani 1 1 d D . . . .
H1WB H 0.4733 0.2240 1.2563 0.041 Uiso 1 1 d DG . . . .
H4A H 0.2674 0.0479 1.3568 0.041 Uiso 1 1 d DG . . . .
H3A H 0.0615 0.2652 1.3208 0.041 Uiso 1 1 d DG . . . .
H4B H 0.0349 0.0333 1.3479 0.041 Uiso 1 1 d DG . . . .
H3B H -0.1332 0.2348 1.2813 0.041 Uiso 1 1 d DG . . . .
H4WA H 0.6853(12) 0.1152(14) 0.5475(12) 0.043(7) Uiso 1 1 d D . . . .
H4WB H 0.599(3) 0.0858(14) 0.4851(7) 0.059(9) Uiso 1 1 d D . . . .


_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 O2 1.9479(11) . ?
Cu1 N1 1.9181(13) . ?
Cu1 O1 1.9913(11) . ?
Cu1 N2 1.9111(13) . ?
O2 C3 1.277(2) . ?
O3 C1 1.2639(19) . ?
O3 Cu2 2.0006(11) . ?
N1 C2 1.300(2) . ?
N1 C5 1.407(2) . ?
O1 C1 1.2532(19) . ?
O4 C2 1.2651(19) . ?
O4 Cu2 1.9894(11) . ?
C1 C2 1.537(2) . ?
N2 C4 1.315(2) . ?
N2 C10 1.4081(19) . ?
C4 C3 1.559(2) . ?
C4 O6 1.2470(19) . ?
C3 O5 1.238(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.394(2) . ?
C6 C5 1.393(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.390(2) . ?
C8 C9 1.390(2) . ?
C10 C5 1.417(2) . ?
C10 C9 1.391(2) . ?
C7 H7 0.9500 . ?
C9 H9 0.9500 . ?
Cu2 N4 1.9821(14) . ?
Cu2 N3 2.0029(14) . ?
Cu2 O1W 2.2852(12) . ?
N4 C12 1.484(2) . ?
N4 H4A 0.9906 . ?
N4 H4B 0.9850 . ?
N3 C11 1.486(2) . ?
N3 H3A 0.9740 . ?
N3 H3B 0.9775 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.511(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
O1W H1WA 0.8906 . ?
O1W H1WB 0.8496 . ?
O3W H3WA 0.8696 . ?
O3W H3WB 0.8701 . ?
O5W H5WA 0.8701 . ?
O5W H5WB 0.8702 . ?
O2W H2WA 0.8698 . ?
O2W H2WB 0.8697 . ?
O4W H4WA 0.8501(10) . ?
O4W H4WB 0.8500(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O1 107.14(5) . . ?
N1 Cu1 O2 167.97(5) . . ?
N1 Cu1 O1 84.54(5) . . ?
N2 Cu1 O2 84.96(5) . . ?
N2 Cu1 N1 83.24(5) . . ?
N2 Cu1 O1 167.57(5) . . ?
C3 O2 Cu1 111.64(10) . . ?
C1 O3 Cu2 112.01(10) . . ?
C2 N1 Cu1 115.07(11) . . ?
C2 N1 C5 130.24(14) . . ?
C5 N1 Cu1 114.69(10) . . ?
C1 O1 Cu1 109.51(10) . . ?
C2 O4 Cu2 110.70(10) . . ?
O3 C1 C2 115.21(14) . . ?
O1 C1 O3 125.05(14) . . ?
O1 C1 C2 119.74(14) . . ?
C4 N2 Cu1 115.61(10) . . ?
C4 N2 C10 129.55(14) . . ?
C10 N2 Cu1 114.82(10) . . ?
N2 C4 C3 110.27(13) . . ?
O6 C4 N2 130.45(15) . . ?
O6 C4 C3 119.26(14) . . ?
O2 C3 C4 117.48(14) . . ?
O5 C3 O2 125.14(15) . . ?
O5 C3 C4 117.37(14) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C7 119.01(15) . . ?
N1 C2 C1 111.12(14) . . ?
O4 C2 N1 130.87(15) . . ?
O4 C2 C1 118.00(14) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C9 C8 C7 120.64(15) . . ?
N2 C10 C5 113.65(13) . . ?
C9 C10 N2 126.68(14) . . ?
C9 C10 C5 119.65(14) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.66(15) . . ?
C8 C7 H7 119.7 . . ?
N1 C5 C10 113.52(13) . . ?
C6 C5 N1 126.07(14) . . ?
C6 C5 C10 120.39(14) . . ?
C8 C9 C10 119.62(15) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
O3 Cu2 N3 94.70(5) . . ?
O3 Cu2 O1W 95.40(4) . . ?
O4 Cu2 O3 83.98(4) . . ?
O4 Cu2 N3 169.58(5) . . ?
O4 Cu2 O1W 93.63(4) . . ?
N4 Cu2 O3 173.88(5) . . ?
N4 Cu2 O4 93.59(5) . . ?
N4 Cu2 N3 86.66(6) . . ?
N4 Cu2 O1W 90.35(5) . . ?
N3 Cu2 O1W 96.78(5) . . ?
Cu2 N4 H4A 112.1 . . ?
Cu2 N4 H4B 112.4 . . ?
C12 N4 Cu2 107.06(11) . . ?
C12 N4 H4A 110.3 . . ?
C12 N4 H4B 109.5 . . ?
H4A N4 H4B 105.6 . . ?
Cu2 N3 H3A 114.2 . . ?
Cu2 N3 H3B 108.0 . . ?
C11 N3 Cu2 107.90(10) . . ?
C11 N3 H3A 111.0 . . ?
C11 N3 H3B 112.9 . . ?
H3A N3 H3B 102.8 . . ?
N4 C12 H12A 110.0 . . ?
N4 C12 H12B 110.0 . . ?
N4 C12 C11 108.34(14) . . ?
H12A C12 H12B 108.4 . . ?
C11 C12 H12A 110.0 . . ?
C11 C12 H12B 110.0 . . ?
N3 C11 C12 108.32(14) . . ?
N3 C11 H11A 110.0 . . ?
N3 C11 H11B 110.0 . . ?
C12 C11 H11A 110.0 . . ?
C12 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
Cu2 O1W H1WA 110.2 . . ?
Cu2 O1W H1WB 116.5 . . ?
H1WA O1W H1WB 106.8 . . ?
H3WA O3W H3WB 104.5 . . ?
H5WA O5W H5WB 104.5 . . ?
H2WA O2W H2WB 104.5 . . ?
H4WA O4W H4WB 96.3(16) . . ?

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
O3W H3WA O5 0.87 1.88 2.7420(17) 172.6 .
O3W H3WB O3 0.87 1.96 2.8049(16) 163.6 4_565
O5W H5WA O4W 0.87 1.88 2.721(2) 162.9 .
O5W H5WB O5 0.87 2.18 2.9439(17) 146.1 .
O2W H2WB O3W 0.87 1.93 2.7918(19) 173.4 4_666
O1W H1WB O2W 0.85 1.88 2.7243(18) 177.6 .
O4W H4WA O3W 0.8501(10) 2.011(10) 2.7953(18) 153(2) 1_655
O4W H4WB O5W 0.8500(10) 1.966(10) 2.7549(19) 154(2) 3_656

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
9 0 0 0.0867 8.9985 -0.0322 -0.0282 -0.2941 -0.2436 -0.8765
-9 0 0 0.0867 -8.9985 0.0322 0.0282 0.2941 0.2436 0.8765
0 -15 19 0.0758 0.0025 -14.9593 18.9872 -0.7219 -0.6127 0.3790
0 15 -19 0.0758 -0.0025 14.9593 -18.9872 0.7219 0.6127 -0.3790
0 20 14 0.0554 0.0116 20.0026 14.0092 0.6557 -0.7757 -0.0282
0 -20 -14 0.0554 -0.0116 -20.0026 -14.0092 -0.6557 0.7757 0.0282

_olex2_submission_special_instructions 'No special instructions were received'
