# 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 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_1
_database_code_depnum_ccdc_archive 'CCDC 1873321'
loop_
_audit_author_name
_audit_author_address
'ANIRBAN karmakar'
;Instituto Superior T?cnico, Universidade de Lisboa
Portugal
;
_audit_update_record             
;
2018-10-15 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C49 H51 Cu4 N9 O25'
_chemical_formula_weight         1420.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.8368(5)
_cell_length_b                   9.9857(6)
_cell_length_c                   16.3956(9)
_cell_angle_alpha                91.165(2)
_cell_angle_beta                 103.967(3)
_cell_angle_gamma                92.411(2)
_cell_volume                     1402.06(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9936
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      26.39

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_F_000             724
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    1.591
_shelx_estimated_absorpt_T_min   0.622
_shelx_estimated_absorpt_T_max   0.763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6
_exptl_absorpt_correction_T_max  0.7
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30829
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.378
_diffrn_reflns_theta_max         26.426
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5744
_reflns_number_gt                4556
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.5.1, 2008'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²+2.7660P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5744
_refine_ls_number_parameters     404
_refine_ls_number_restraints     131
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.09012(6) 0.52698(4) 0.08700(2) 0.04130(16) Uani 1 1 d D U . . .
Cu2 Cu 0.13296(10) 0.75412(7) -0.05502(4) 0.03518(19) Uani 0.87 1 d . U P . .
O2 O 0.0647(3) 0.4815(2) 0.19572(14) 0.0418(6) Uani 1 1 d . U . . .
O4 O 0.7298(3) 0.9997(2) 0.49904(15) 0.0416(6) Uani 1 1 d . U . . .
O12 O 0.7985(4) 0.2236(3) 0.60593(17) 0.0475(7) Uani 1 1 d . U . . .
H12O H 0.7780 0.1574 0.5741 0.071 Uiso 1 1 calc R U . . .
O1 O -0.0603(4) 0.2789(2) 0.17507(14) 0.0449(7) Uani 1 1 d . U . . .
O6 O 0.2476(4) 0.6586(3) 0.14426(15) 0.0507(8) Uani 1 1 d . U . . .
O7 O 0.1121(3) 0.5659(3) -0.02679(15) 0.0422(6) Uani 1 1 d D U . . .
O8 O 0.1382(4) 0.9474(3) -0.07824(17) 0.0536(8) Uani 1 1 d D U . . .
O5 O 0.2711(4) 0.8108(3) 0.05052(16) 0.0564(9) Uani 1 1 d . U . . .
N2 N 0.5018(3) 0.7244(3) 0.54569(16) 0.0286(6) Uani 1 1 d . U . . .
N3 N 0.5669(4) 0.8416(3) 0.41632(17) 0.0344(7) Uani 1 1 d . U . . .
O3 O 0.3372(4) 0.4511(3) 0.63309(16) 0.0565(8) Uani 1 1 d . U . . .
N1 N 0.2755(4) 0.5367(3) 0.50180(17) 0.0332(7) Uani 1 1 d . U . . .
C17 C 0.4267(4) 0.8415(3) 0.18757(19) 0.0278(7) Uani 1 1 d . U . . .
C16 C 0.4489(4) 0.8076(3) 0.27073(19) 0.0286(7) Uani 1 1 d . U . . .
H16 H 0.3902 0.7362 0.2849 0.034 Uiso 1 1 calc R U . . .
C1 C 0.0094(4) 0.3767(3) 0.22049(19) 0.0274(7) Uani 1 1 d . U . . .
C2 C 0.0316(4) 0.3652(3) 0.31343(19) 0.0269(7) Uani 1 1 d . U . . .
C6 C 0.1666(4) 0.4419(3) 0.45338(19) 0.0265(6) Uani 1 1 d . U . . .
C7 C 0.1360(4) 0.4538(3) 0.36675(19) 0.0266(7) Uani 1 1 d . U . . .
H7 H 0.1864 0.5222 0.3443 0.032 Uiso 1 1 calc R U . . .
C15 C 0.5584(4) 0.8793(3) 0.33345(19) 0.0297(7) Uani 1 1 d . U . . .
C21 C 0.3059(4) 0.7632(3) 0.12157(19) 0.0276(7) Uani 1 1 d . U . . .
C13 C 0.6076(4) 0.8275(3) 0.56459(19) 0.0284(7) Uani 1 1 d . U . . .
C14 C 0.6421(4) 0.8992(3) 0.4904(2) 0.0287(7) Uani 1 1 d . U . . .
C9 C 0.4697(4) 0.6543(3) 0.60849(19) 0.0296(7) Uani 1 1 d . U . . .
C5 C 0.0905(4) 0.3402(3) 0.4873(2) 0.0335(8) Uani 1 1 d . U . . .
H5 H 0.1101 0.3315 0.5452 0.040 Uiso 1 1 calc R U . . .
C18 C 0.5148(5) 0.9465(4) 0.1652(2) 0.0379(8) Uani 1 1 d . U . . .
H18 H 0.4996 0.9701 0.1093 0.046 Uiso 1 1 calc R U . . .
C3 C -0.0445(4) 0.2632(4) 0.3471(2) 0.0355(8) Uani 1 1 d . U . . .
H3 H -0.1148 0.2029 0.3117 0.043 Uiso 1 1 calc R U . . .
C8 C 0.3531(4) 0.5369(3) 0.5832(2) 0.0328(7) Uani 1 1 d . U . . .
C12 C 0.6817(4) 0.8657(4) 0.6467(2) 0.0344(8) Uani 1 1 d . U . . .
H12 H 0.7533 0.9387 0.6581 0.041 Uiso 1 1 calc R U . . .
C4 C -0.0148(4) 0.2520(4) 0.4334(2) 0.0389(9) Uani 1 1 d . U . . .
H4 H -0.0664 0.1842 0.4557 0.047 Uiso 1 1 calc R U . . .
O9 O 0.2730(6) 0.3527(4) 0.0855(3) 0.0957(14) Uani 1 1 d . U . . .
C10 C 0.5409(5) 0.6845(4) 0.6925(2) 0.0376(8) Uani 1 1 d . U . . .
H10 H 0.5177 0.6331 0.7349 0.045 Uiso 1 1 calc R U . . .
C20 C 0.6484(4) 0.9839(4) 0.3116(2) 0.0384(8) Uani 1 1 d . U . . .
H20 H 0.7227 1.0320 0.3528 0.046 Uiso 1 1 calc R U . . .
N4 N 0.2305(7) 0.2477(5) 0.0383(3) 0.0712(12) Uani 1 1 d . U . . .
C19 C 0.6260(5) 1.0155(4) 0.2278(2) 0.0476(10) Uani 1 1 d . U . . .
H19 H 0.6871 1.0847 0.2132 0.057 Uiso 1 1 calc R U . . .
C11 C 0.6469(5) 0.7929(4) 0.7113(2) 0.0401(9) Uani 1 1 d . U . . .
H11 H 0.6945 0.8168 0.7670 0.048 Uiso 1 1 calc R U . . .
C23 C 0.9356(6) 0.2048(5) 0.6677(3) 0.0628(13) Uani 1 1 d . U . . .
H01A H 0.9954 0.2884 0.6802 0.094 Uiso 1 1 calc R U . . .
H01B H 0.9960 0.1399 0.6474 0.094 Uiso 1 1 calc R U . . .
H01C H 0.9093 0.1733 0.7177 0.094 Uiso 1 1 calc R U . . .
O11 O 0.3310(8) 0.1793(7) 0.0285(4) 0.148(3) Uani 1 1 d . U . . .
O10A O 0.0865(10) 0.2365(18) -0.0043(10) 0.089(4) Uani 0.67(4) 1 d . U P A 1
O10B O 0.126(4) 0.180(3) 0.031(2) 0.106(6) Uani 0.33(4) 1 d . U P A 2
C22 C 0.0293(7) 1.0132(5) -0.1408(3) 0.0701(15) Uani 1 1 d . U . . .
H01D H 0.0246 0.9725 -0.1950 0.105 Uiso 1 1 calc R U . . .
H01E H 0.0615 1.1063 -0.1407 0.105 Uiso 1 1 calc R U . . .
H01F H -0.0720 1.0055 -0.1291 0.105 Uiso 1 1 calc R U . . .
Cu2A Cu 0.1915(6) 0.7138(5) -0.0619(3) 0.0331(11) Uani 0.13 1 d . U P . .
H1N H 0.286(5) 0.591(4) 0.477(3) 0.040 Uiso 1 1 d . U . . .
H3N H 0.516(5) 0.780(4) 0.420(3) 0.040 Uiso 1 1 d . U . . .
H8O H 0.170(5) 1.000(4) -0.0344(19) 0.050 Uiso 1 1 d D U . . .
H7O H 0.203(3) 0.520(4) -0.023(2) 0.050 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 O2 1.911(2) . ?
Cu1 O6 1.927(2) . ?
Cu1 O7 1.967(3) . ?
Cu1 O7 2.000(3) 2_565 ?
Cu1 O9 2.428(4) . ?
Cu1 Cu1 2.9391(8) 2_565 ?
Cu2 Cu2A 0.698(5) . ?
Cu2 O5 1.920(3) . ?
Cu2 O1 1.934(2) 2_565 ?
Cu2 O7 1.957(3) . ?
Cu2 O8 1.975(3) . ?
Cu2 O10A 2.375(9) 2_565 ?
O2 C1 1.253(4) . ?
O4 C14 1.225(4) . ?
O12 C23 1.401(5) . ?
O12 H12O 0.8200 . ?
O1 C1 1.259(4) . ?
O1 Cu2 1.934(2) 2_565 ?
O1 Cu2A 1.940(5) 2_565 ?
O6 C21 1.248(4) . ?
O7 Cu2A 1.775(5) . ?
O7 Cu1 2.000(3) 2_565 ?
O7 H7O 0.928(19) . ?
O8 C22 1.420(5) . ?
O8 Cu2A 2.406(6) . ?
O8 H8O 0.866(19) . ?
O5 C21 1.241(4) . ?
O5 Cu2A 2.019(5) . ?
N2 C9 1.335(4) . ?
N2 C13 1.341(4) . ?
N3 C14 1.341(4) . ?
N3 C15 1.403(4) . ?
N3 H3N 0.75(4) . ?
O3 C8 1.223(4) . ?
N1 C8 1.346(4) . ?
N1 C6 1.406(4) . ?
N1 H1N 0.70(4) . ?
C17 C16 1.381(4) . ?
C17 C18 1.387(4) . ?
C17 C21 1.504(4) . ?
C16 C15 1.393(4) . ?
C16 H16 0.9300 . ?
C1 C2 1.496(4) . ?
C2 C7 1.381(4) . ?
C2 C3 1.392(4) . ?
C6 C7 1.389(4) . ?
C6 C5 1.393(4) . ?
C7 H7 0.9300 . ?
C15 C20 1.390(5) . ?
C13 C12 1.385(4) . ?
C13 C14 1.511(4) . ?
C9 C10 1.390(4) . ?
C9 C8 1.511(5) . ?
C5 C4 1.387(5) . ?
C5 H5 0.9300 . ?
C18 C19 1.387(5) . ?
C18 H18 0.9300 . ?
C3 C4 1.384(5) . ?
C3 H3 0.9300 . ?
C12 C11 1.385(5) . ?
C12 H12 0.9300 . ?
C4 H4 0.9300 . ?
O9 N4 1.279(6) . ?
C10 C11 1.380(5) . ?
C10 H10 0.9300 . ?
C20 C19 1.385(5) . ?
C20 H20 0.9300 . ?
N4 O10B 1.11(2) . ?
N4 O11 1.181(7) . ?
N4 O10A 1.294(12) . ?
C19 H19 0.9300 . ?
C11 H11 0.9300 . ?
C23 H01A 0.9600 . ?
C23 H01B 0.9600 . ?
C23 H01C 0.9600 . ?
O10A Cu2 2.375(9) 2_565 ?
C22 H01D 0.9600 . ?
C22 H01E 0.9600 . ?
C22 H01F 0.9600 . ?
Cu2A O1 1.940(5) 2_565 ?
Cu2A H7O 2.05(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O6 86.65(10) . . ?
O2 Cu1 O7 177.45(10) . . ?
O6 Cu1 O7 95.73(11) . . ?
O2 Cu1 O7 93.60(11) . 2_565 ?
O6 Cu1 O7 163.77(13) . 2_565 ?
O7 Cu1 O7 84.39(12) . 2_565 ?
O2 Cu1 O9 92.88(14) . . ?
O6 Cu1 O9 94.57(15) . . ?
O7 Cu1 O9 86.00(14) . . ?
O7 Cu1 O9 101.63(14) 2_565 . ?
O2 Cu1 Cu1 135.33(8) . 2_565 ?
O6 Cu1 Cu1 136.07(8) . 2_565 ?
O7 Cu1 Cu1 42.63(8) . 2_565 ?
O7 Cu1 Cu1 41.76(7) 2_565 2_565 ?
O9 Cu1 Cu1 95.19(10) . 2_565 ?
Cu2A Cu2 O5 87.9(4) . . ?
Cu2A Cu2 O1 80.1(4) . 2_565 ?
O5 Cu2 O1 158.77(14) . 2_565 ?
Cu2A Cu2 O7 64.7(4) . . ?
O5 Cu2 O7 95.87(11) . . ?
O1 Cu2 O7 94.76(10) 2_565 . ?
Cu2A Cu2 O8 120.5(4) . . ?
O5 Cu2 O8 83.67(12) . . ?
O1 Cu2 O8 87.40(11) 2_565 . ?
O7 Cu2 O8 174.66(15) . . ?
Cu2A Cu2 O10A 144.8(7) . 2_565 ?
O5 Cu2 O10A 91.0(3) . 2_565 ?
O1 Cu2 O10A 108.9(3) 2_565 2_565 ?
O7 Cu2 O10A 80.4(5) . 2_565 ?
O8 Cu2 O10A 94.3(5) . 2_565 ?
C1 O2 Cu1 130.8(2) . . ?
C23 O12 H12O 109.5 . . ?
C1 O1 Cu2 134.2(2) . 2_565 ?
C1 O1 Cu2A 126.7(3) . 2_565 ?
C21 O6 Cu1 133.3(2) . . ?
Cu2A O7 Cu1 128.4(2) . . ?
Cu2 O7 Cu1 117.73(13) . . ?
Cu2A O7 Cu1 123.9(2) . 2_565 ?
Cu2 O7 Cu1 114.02(14) . 2_565 ?
Cu1 O7 Cu1 95.61(12) . 2_565 ?
Cu2A O7 H7O 93(3) . . ?
Cu2 O7 H7O 113(3) . . ?
Cu1 O7 H7O 96(2) . . ?
Cu1 O7 H7O 118(3) 2_565 . ?
C22 O8 Cu2 126.3(3) . . ?
C22 O8 Cu2A 131.0(3) . . ?
C22 O8 H8O 109(3) . . ?
Cu2 O8 H8O 115(3) . . ?
Cu2A O8 H8O 118(3) . . ?
C21 O5 Cu2 134.5(2) . . ?
C21 O5 Cu2A 128.7(3) . . ?
C9 N2 C13 118.5(3) . . ?
C14 N3 C15 131.4(3) . . ?
C14 N3 H3N 114(3) . . ?
C15 N3 H3N 114(3) . . ?
C8 N1 C6 130.4(3) . . ?
C8 N1 H1N 120(4) . . ?
C6 N1 H1N 110(4) . . ?
C16 C17 C18 120.5(3) . . ?
C16 C17 C21 119.1(3) . . ?
C18 C17 C21 120.4(3) . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
O2 C1 O1 126.5(3) . . ?
O2 C1 C2 116.7(3) . . ?
O1 C1 C2 116.8(3) . . ?
C7 C2 C3 119.5(3) . . ?
C7 C2 C1 119.0(3) . . ?
C3 C2 C1 121.4(3) . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 N1 116.2(3) . . ?
C5 C6 N1 124.0(3) . . ?
C2 C7 C6 120.9(3) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C20 C15 C16 119.5(3) . . ?
C20 C15 N3 124.2(3) . . ?
C16 C15 N3 116.3(3) . . ?
O5 C21 O6 126.5(3) . . ?
O5 C21 C17 116.7(3) . . ?
O6 C21 C17 116.8(3) . . ?
N2 C13 C12 122.4(3) . . ?
N2 C13 C14 115.7(3) . . ?
C12 C13 C14 121.9(3) . . ?
O4 C14 N3 125.0(3) . . ?
O4 C14 C13 122.2(3) . . ?
N3 C14 C13 112.9(3) . . ?
N2 C9 C10 122.7(3) . . ?
N2 C9 C8 116.1(3) . . ?
C10 C9 C8 121.2(3) . . ?
C4 C5 C6 119.0(3) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C19 C18 C17 118.6(3) . . ?
C19 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
O3 C8 N1 125.3(3) . . ?
O3 C8 C9 121.6(3) . . ?
N1 C8 C9 113.0(3) . . ?
C11 C12 C13 118.5(3) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C3 C4 C5 121.2(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
N4 O9 Cu1 120.0(4) . . ?
C11 C10 C9 118.3(3) . . ?
C11 C10 H10 120.8 . . ?
C9 C10 H10 120.8 . . ?
C19 C20 C15 119.2(3) . . ?
C19 C20 H20 120.4 . . ?
C15 C20 H20 120.4 . . ?
O10B N4 O11 106.0(19) . . ?
O10B N4 O9 129.4(12) . . ?
O11 N4 O9 116.5(6) . . ?
O11 N4 O10A 125.3(7) . . ?
O9 N4 O10A 117.4(7) . . ?
C20 C19 C18 121.7(3) . . ?
C20 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C10 C11 C12 119.5(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
O12 C23 H01A 109.5 . . ?
O12 C23 H01B 109.5 . . ?
H01A C23 H01B 109.5 . . ?
O12 C23 H01C 109.5 . . ?
H01A C23 H01C 109.5 . . ?
H01B C23 H01C 109.5 . . ?
N4 O10A Cu2 124.7(9) . 2_565 ?
O8 C22 H01D 109.5 . . ?
O8 C22 H01E 109.5 . . ?
H01D C22 H01E 109.5 . . ?
O8 C22 H01F 109.5 . . ?
H01D C22 H01F 109.5 . . ?
H01E C22 H01F 109.5 . . ?
Cu2 Cu2A O7 94.5(5) . . ?
Cu2 Cu2A O1 79.1(5) . 2_565 ?
O7 Cu2A O1 100.7(2) . 2_565 ?
Cu2 Cu2A O5 71.9(4) . . ?
O7 Cu2A O5 98.5(2) . . ?
O1 Cu2A O5 146.2(3) 2_565 . ?
Cu2 Cu2A O8 45.0(4) . . ?
O7 Cu2A O8 139.5(3) . . ?
O1 Cu2A O8 76.0(2) 2_565 . ?
O5 Cu2A O8 71.31(18) . . ?
Cu2 Cu2A H7O 120.4(8) . . ?
O7 Cu2A H7O 26.9(7) . . ?
O1 Cu2A H7O 110.5(11) 2_565 . ?
O5 Cu2A H7O 99.1(11) . . ?
O8 Cu2A H7O 163.9(8) . . ?

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
O12 H12O O4 0.82 1.95 2.766(3) 179.7 1_545
C7 H7 O12 0.93 2.64 3.252(4) 124.1 2_666
C5 H5 O3 0.93 2.42 2.977(4) 118.3 .
C20 H20 O4 0.93 2.41 2.981(4) 119.5 .
C22 H01E O10A 0.96 2.52 3.064(9) 115.8 1_565
C22 H01F O10B 0.96 2.58 3.15(3) 118.5 2_565
N1 H1N O12 0.70(4) 2.36(4) 3.004(4) 154(5) 2_666
N1 H1N N2 0.70(4) 2.31(4) 2.639(4) 110(4) .
N3 H3N N2 0.75(4) 2.18(4) 2.614(4) 118(4) .
O8 H8O N4 0.866(19) 2.70(3) 3.481(6) 151(4) 1_565
O8 H8O O11 0.866(19) 2.30(3) 3.064(8) 147(4) 1_565
O8 H8O O10A 0.866(19) 2.57(4) 3.201(13) 130(4) 1_565
O8 H8O O10B 0.866(19) 2.17(4) 2.93(2) 146(4) 1_565
O7 H7O O9 0.928(19) 2.45(3) 3.016(5) 119(3) .

_refine_diff_density_max         1.568
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.084

_shelxl_version_number           2014/6


####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1873322'
loop_
_audit_author_name
_audit_author_address
'ANIRBAN karmakar'
;Instituto Superior T?cnico, Universidade de Lisboa
Portugal
;
_audit_update_record             
;
2018-10-15 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H27 Cu N5 O8'
_chemical_formula_weight         613.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   9.1236(8)
_cell_length_b                   15.7177(14)
_cell_length_c                   19.9209(17)
_cell_angle_alpha                90
_cell_angle_beta                 93.270(2)
_cell_angle_gamma                90
_cell_volume                     2852.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5336
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      25.23

_exptl_crystal_description       Block
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             1268
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.823
_shelx_estimated_absorpt_T_min   0.790
_shelx_estimated_absorpt_T_max   0.880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45098
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_av_R_equivalents  0.1318
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.424
_diffrn_reflns_theta_max         25.382
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5202
_reflns_number_gt                3161
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury CSD 3.5.1, 2008'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+4.5128P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5202
_refine_ls_number_parameters     334
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.37374(6) 1.04009(4) 0.49922(2) 0.03615(17) Uani 1 1 d . . . . .
O6 O 1.1129(3) 0.5454(2) 0.09905(13) 0.0459(8) Uani 1 1 d . . . . .
O2 O 0.5059(3) 0.85693(19) 0.49154(14) 0.0442(8) Uani 1 1 d . . . . .
O5 O 0.8978(3) 0.4767(2) 0.09637(14) 0.0463(8) Uani 1 1 d . . . . .
O1 O 0.2904(3) 0.9260(2) 0.49255(16) 0.0508(8) Uani 1 1 d . . . . .
N2 N 0.4901(4) 0.4279(2) 0.39310(16) 0.0421(9) Uani 1 1 d . . . . .
O7 O 0.1656(4) 1.1022(2) 0.50392(17) 0.0653(11) Uani 1 1 d . . . . .
O3 O 0.2278(4) 0.4499(2) 0.51588(19) 0.0748(11) Uani 1 1 d . . . . .
N1 N 0.3383(4) 0.5513(3) 0.45436(17) 0.0418(9) Uani 1 1 d . . . . .
O4 O 0.7225(4) 0.3445(3) 0.27467(18) 0.0781(12) Uani 1 1 d . . . . .
N3 N 0.7385(5) 0.4694(3) 0.33164(18) 0.0548(12) Uani 1 1 d . . . . .
C7 C 0.3485(5) 0.7018(3) 0.4748(2) 0.0411(11) Uani 1 1 d . . . . .
H7 H 0.4384 0.7028 0.4550 0.049 Uiso 1 1 calc R U . . .
C21 C 1.0023(5) 0.5147(3) 0.1258(2) 0.0376(11) Uani 1 1 d . . . . .
C2 C 0.2895(5) 0.7764(3) 0.4978(2) 0.0420(11) Uani 1 1 d . . . . .
C1 C 0.3682(5) 0.8599(3) 0.49313(19) 0.0386(10) Uani 1 1 d . . . . .
C9 C 0.3792(5) 0.4037(3) 0.4301(2) 0.0424(11) Uani 1 1 d . . . . .
C6 C 0.2743(5) 0.6250(3) 0.48112(19) 0.0384(11) Uani 1 1 d . . . . .
C19 C 0.9935(5) 0.5266(3) 0.20068(19) 0.0416(11) Uani 1 1 d . . . . .
C13 C 0.5508(5) 0.3675(3) 0.3564(2) 0.0433(11) Uani 1 1 d . . . . .
C20 C 0.8736(5) 0.4931(3) 0.2311(2) 0.0448(12) Uani 1 1 d . . . . .
H20 H 0.8023 0.4632 0.2055 0.054 Uiso 1 1 calc R U . . .
C8 C 0.3082(5) 0.4704(3) 0.4709(2) 0.0459(12) Uani 1 1 d . . . . .
C15 C 0.8594(5) 0.5040(3) 0.2998(2) 0.0500(13) Uani 1 1 d . . . . .
C14 C 0.6784(5) 0.3932(4) 0.3168(2) 0.0520(13) Uani 1 1 d . . . . .
C3 C 0.1571(5) 0.7735(4) 0.5297(2) 0.0532(13) Uani 1 1 d . . . . .
H3 H 0.1170 0.8231 0.5463 0.064 Uiso 1 1 calc R U . . .
C10 C 0.3281(5) 0.3209(4) 0.4313(3) 0.0540(13) Uani 1 1 d . . . . .
H10 H 0.2531 0.3063 0.4589 0.065 Uiso 1 1 calc R U . . .
C18 C 1.0985(6) 0.5715(3) 0.2386(2) 0.0567(14) Uani 1 1 d . . . . .
H18 H 1.1797 0.5939 0.2185 0.068 Uiso 1 1 calc R U . . .
C5 C 0.1424(5) 0.6232(4) 0.5115(2) 0.0536(13) Uani 1 1 d . . . . .
H5 H 0.0916 0.5722 0.5152 0.064 Uiso 1 1 calc R U . . .
C11 C 0.3883(5) 0.2607(4) 0.3921(2) 0.0543(13) Uani 1 1 d . . . . .
H11 H 0.3538 0.2050 0.3916 0.065 Uiso 1 1 calc R U . . .
C12 C 0.5020(5) 0.2844(3) 0.3531(2) 0.0536(13) Uani 1 1 d . . . . .
H12 H 0.5447 0.2452 0.3252 0.064 Uiso 1 1 calc R U . . .
C16 C 0.9647(6) 0.5499(4) 0.3371(2) 0.0640(15) Uani 1 1 d . . . . .
H16 H 0.9555 0.5583 0.3829 0.077 Uiso 1 1 calc R U . . .
C4 C 0.0867(5) 0.6973(4) 0.5362(3) 0.0623(15) Uani 1 1 d . . . . .
H4 H -0.0008 0.6957 0.5579 0.075 Uiso 1 1 calc R U . . .
C17 C 1.0823(6) 0.5829(4) 0.3064(2) 0.0739(18) Uani 1 1 d . . . . .
H17 H 1.1528 0.6137 0.3317 0.089 Uiso 1 1 calc R U . . .
N4 N 0.0701(6) 1.1465(5) 0.5990(2) 0.0914(18) Uani 1 1 d . U . . .
C22 C 0.0792(6) 1.0968(5) 0.5476(3) 0.081(2) Uani 1 1 d . . . . .
H22 H 0.0122 1.0523 0.5438 0.098 Uiso 1 1 calc R U . . .
C23 C 0.1750(12) 1.2154(6) 0.6078(4) 0.150(4) Uani 1 1 d . U . . .
H23A H 0.1237 1.2677 0.6146 0.225 Uiso 1 1 calc R U . . .
H23B H 0.2303 1.2201 0.5684 0.225 Uiso 1 1 calc R U . . .
H23C H 0.2404 1.2039 0.6462 0.225 Uiso 1 1 calc R U . . .
C24 C -0.0468(9) 1.1454(8) 0.6437(4) 0.159(4) Uani 1 1 d . U . . .
H24A H -0.0091 1.1600 0.6882 0.239 Uiso 1 1 calc R U . . .
H24B H -0.0894 1.0896 0.6442 0.239 Uiso 1 1 calc R U . . .
H24C H -0.1203 1.1860 0.6289 0.239 Uiso 1 1 calc R U . . .
H3N H 0.685(10) 0.500(6) 0.371(5) 0.191 Uiso 1 1 d . U . . .
H1N H 0.406(10) 0.556(6) 0.420(5) 0.191 Uiso 1 1 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 1.949(3) . ?
Cu1 O5 1.953(3) 4_576 ?
Cu1 O2 1.959(3) 3_676 ?
Cu1 O6 1.970(3) 2_655 ?
Cu1 O7 2.142(3) . ?
Cu1 Cu1 2.6246(10) 3_676 ?
O6 C21 1.264(5) . ?
O6 Cu1 1.970(3) 2_645 ?
O2 C1 1.260(5) . ?
O2 Cu1 1.959(3) 3_676 ?
O5 C21 1.244(5) . ?
O5 Cu1 1.953(3) 4_675 ?
O1 C1 1.258(5) . ?
N2 C13 1.336(6) . ?
N2 C9 1.340(5) . ?
O7 C22 1.209(6) . ?
O3 C8 1.233(5) . ?
N1 C8 1.345(6) . ?
N1 C6 1.416(6) . ?
N1 H1N 0.95(9) . ?
O4 C14 1.221(5) . ?
N3 C14 1.343(6) . ?
N3 C15 1.412(6) . ?
N3 H3N 1.06(9) . ?
C7 C2 1.380(6) . ?
C7 C6 1.393(6) . ?
C7 H7 0.9300 . ?
C21 C19 1.509(5) . ?
C2 C3 1.396(6) . ?
C2 C1 1.501(7) . ?
C9 C10 1.384(7) . ?
C9 C8 1.496(7) . ?
C6 C5 1.378(6) . ?
C19 C18 1.379(6) . ?
C19 C20 1.384(6) . ?
C13 C12 1.381(7) . ?
C13 C14 1.499(6) . ?
C20 C15 1.394(6) . ?
C20 H20 0.9300 . ?
C15 C16 1.383(7) . ?
C3 C4 1.369(7) . ?
C3 H3 0.9300 . ?
C10 C11 1.362(7) . ?
C10 H10 0.9300 . ?
C18 C17 1.379(6) . ?
C18 H18 0.9300 . ?
C5 C4 1.374(7) . ?
C5 H5 0.9300 . ?
C11 C12 1.382(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C16 C17 1.368(7) . ?
C16 H16 0.9300 . ?
C4 H4 0.9300 . ?
C17 H17 0.9300 . ?
N4 C22 1.294(7) . ?
N4 C24 1.428(9) . ?
N4 C23 1.449(10) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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 O5 87.98(14) . 4_576 ?
O1 Cu1 O2 168.82(13) . 3_676 ?
O5 Cu1 O2 89.30(13) 4_576 3_676 ?
O1 Cu1 O6 91.00(14) . 2_655 ?
O5 Cu1 O6 168.69(12) 4_576 2_655 ?
O2 Cu1 O6 89.54(13) 3_676 2_655 ?
O1 Cu1 O7 94.51(14) . . ?
O5 Cu1 O7 93.89(13) 4_576 . ?
O2 Cu1 O7 96.50(14) 3_676 . ?
O6 Cu1 O7 97.42(12) 2_655 . ?
O1 Cu1 Cu1 84.14(10) . 3_676 ?
O5 Cu1 Cu1 82.80(9) 4_576 3_676 ?
O2 Cu1 Cu1 84.75(9) 3_676 3_676 ?
O6 Cu1 Cu1 85.89(9) 2_655 3_676 ?
O7 Cu1 Cu1 176.46(10) . 3_676 ?
C21 O6 Cu1 120.0(3) . 2_645 ?
C1 O2 Cu1 121.4(3) . 3_676 ?
C21 O5 Cu1 124.9(3) . 4_675 ?
C1 O1 Cu1 122.8(3) . . ?
C13 N2 C9 116.7(4) . . ?
C22 O7 Cu1 128.0(4) . . ?
C8 N1 C6 126.0(4) . . ?
C8 N1 H1N 113(6) . . ?
C6 N1 H1N 121(6) . . ?
C14 N3 C15 124.3(4) . . ?
C14 N3 H3N 111(5) . . ?
C15 N3 H3N 124(5) . . ?
C2 C7 C6 120.4(4) . . ?
C2 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
O5 C21 O6 126.4(4) . . ?
O5 C21 C19 116.3(4) . . ?
O6 C21 C19 117.3(4) . . ?
C7 C2 C3 119.1(5) . . ?
C7 C2 C1 121.7(4) . . ?
C3 C2 C1 119.1(4) . . ?
O1 C1 O2 126.4(4) . . ?
O1 C1 C2 116.8(4) . . ?
O2 C1 C2 116.8(4) . . ?
N2 C9 C10 122.8(4) . . ?
N2 C9 C8 117.7(4) . . ?
C10 C9 C8 119.5(4) . . ?
C5 C6 C7 119.9(5) . . ?
C5 C6 N1 122.5(4) . . ?
C7 C6 N1 117.6(4) . . ?
C18 C19 C20 119.8(4) . . ?
C18 C19 C21 122.0(4) . . ?
C20 C19 C21 118.2(4) . . ?
N2 C13 C12 123.7(4) . . ?
N2 C13 C14 117.1(4) . . ?
C12 C13 C14 119.2(5) . . ?
C19 C20 C15 120.2(4) . . ?
C19 C20 H20 119.9 . . ?
C15 C20 H20 119.9 . . ?
O3 C8 N1 124.3(5) . . ?
O3 C8 C9 120.4(5) . . ?
N1 C8 C9 115.3(4) . . ?
C16 C15 C20 119.4(4) . . ?
C16 C15 N3 119.8(4) . . ?
C20 C15 N3 120.8(4) . . ?
O4 C14 N3 124.4(4) . . ?
O4 C14 C13 119.3(5) . . ?
N3 C14 C13 116.3(4) . . ?
C4 C3 C2 119.7(5) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C11 C10 C9 119.7(5) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C17 C18 C19 119.5(4) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C4 C5 C6 119.3(5) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C10 C11 C12 118.4(5) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C13 C12 C11 118.6(5) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C17 C16 C15 119.8(4) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C3 C4 C5 121.5(5) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C16 C17 C18 121.3(5) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C22 N4 C24 124.8(8) . . ?
C22 N4 C23 118.3(7) . . ?
C24 N4 C23 116.4(7) . . ?
O7 C22 N4 127.0(7) . . ?
O7 C22 H22 116.5 . . ?
N4 C22 H22 116.5 . . ?
N4 C23 H23A 109.5 . . ?
N4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N4 C24 H24A 109.5 . . ?
N4 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N4 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
C5 H5 O3 0.93 2.29 2.833(7) 116.8 .
C24 H24A O4 0.96 2.65 3.483(10) 145.5 4_576
N3 H3N O3 1.06(9) 2.47(9) 3.290(5) 133(6) 3_666
N1 H1N N2 0.95(9) 2.23(9) 2.713(6) 111(7) .
C5 H5 O3 0.93 2.29 2.833(7) 116.8 .
C24 H24A O4 0.96 2.65 3.483(10) 145.5 4_576
N3 H3N O3 1.06(9) 2.47(9) 3.290(5) 133(6) 3_666
N1 H1N N2 0.95(9) 2.23(9) 2.713(6) 111(7) .

_refine_diff_density_max         0.810
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.066

_shelxl_version_number           2014/6





