# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1124-yf-jm-n13-2-01
_database_code_depnum_ccdc_archive 'CCDC 1500703'
_audit_update_record             
;
2016-08-23 deposited with the CCDC.
2016-11-11 downloaded from the CCDC.
;
_audit_creation_date             2016-05-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'Cl, C17 H14 N3 O2, H2 O'
_chemical_formula_sum            'C17 H16 Cl N3 O3'
_chemical_formula_weight         345.78
_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 0.0033 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   7.2591(3)
_cell_length_b                   18.7570(10)
_cell_length_c                   12.2090(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.578(4)
_cell_angle_gamma                90.00
_cell_volume                     1615.90(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2199
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.5247
_cell_measurement_theta_min      2.8809
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85852
_exptl_absorpt_correction_type   multi-scan
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'yellowish yellow'
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7902
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         2.89
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 15.9784
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -14.00   16.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2889  -99.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega  -48.00   40.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3827  -57.0000 -120.0000 88

#__ type_ start__ end____ width___ exp.time_
  3 omega   23.00   49.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3827   57.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   -3.00   88.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3827  -19.0000  -90.0000 91

#__ type_ start__ end____ width___ exp.time_
  5 omega  -45.00    5.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3827   19.0000   30.0000 50
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0059405000
_diffrn_orient_matrix_UB_12      -0.0355549000
_diffrn_orient_matrix_UB_13      -0.0202195000
_diffrn_orient_matrix_UB_21      -0.0900879000
_diffrn_orient_matrix_UB_22      0.0074886000
_diffrn_orient_matrix_UB_23      -0.0356661000
_diffrn_orient_matrix_UB_31      0.0442309000
_diffrn_orient_matrix_UB_32      0.0103973000
_diffrn_orient_matrix_UB_33      -0.0435143000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2083
_reflns_number_total             3289
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0422P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1135
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C11(H11), C4(H4), C8(H8), C10(H10), C5(H5), C13(H13), C2(H2B),
  C14(H14), C16(H16), C1(H1A), C15(H15)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl -0.22931(9) 0.38163(4) 0.28550(5) 0.0572(2) Uani 1 d . . .
N1 N -0.4725(2) 0.41201(10) -0.22016(14) 0.0347(4) Uani 1 d . . .
H1 H -0.4353 0.4557 -0.2135 0.042 Uiso 1 calc . . R
N2 N -0.1925(2) 0.49383(10) 0.08170(14) 0.0415(5) Uani 1 d . . .
H2 H -0.1692 0.4688 0.1424 0.050 Uiso 1 calc . . R
N3 N -0.2855(2) 0.46568(11) -0.01845(14) 0.0390(5) Uani 1 d . . .
C17 C -0.5648(3) 0.38760(12) -0.32466(17) 0.0326(5) Uani 1 d . . .
O1 O -0.1714(2) 0.59906(9) -0.00466(13) 0.0540(5) Uani 1 d . . .
O3 O -0.3654(2) 0.55324(10) -0.22541(13) 0.0567(5) Uani 1 d . . .
H3A H -0.4708 0.5751 -0.2381 0.085 Uiso 1 d . . G
H3B H -0.3072 0.5592 -0.1570 0.085 Uiso 1 d . . G
C6 C -0.0364(3) 0.59396(13) 0.19244(18) 0.0342(5) Uani 1 d . . .
O2 O 0.2165(2) 0.69532(9) 0.49028(13) 0.0556(5) Uani 1 d . . .
H2A H 0.2295 0.6681 0.5441 0.083 Uiso 1 calc . . GR
C12 C -0.6231(3) 0.31603(12) -0.33663(18) 0.0352(5) Uani 1 d . . .
C9 C -0.4382(3) 0.37079(13) -0.12865(17) 0.0339(5) Uani 1 d . . .
C11 C -0.5850(3) 0.27286(13) -0.24034(18) 0.0411(6) Uani 1 d . . .
H11 H -0.6213 0.2252 -0.2463 0.049 Uiso 1 calc . . R
C4 C 0.0842(3) 0.58937(13) 0.39347(18) 0.0393(6) Uani 1 d . . .
H4 H 0.1070 0.5638 0.4605 0.047 Uiso 1 calc . . R
C3 C 0.1368(3) 0.65979(13) 0.39410(18) 0.0383(6) Uani 1 d . . .
C8 C -0.3379(3) 0.40088(14) -0.02075(18) 0.0403(6) Uani 1 d . . .
H8 H -0.3131 0.3734 0.0445 0.048 Uiso 1 calc . . R
C10 C -0.4955(3) 0.29981(13) -0.13806(18) 0.0410(6) Uani 1 d . . .
H10 H -0.4727 0.2708 -0.0745 0.049 Uiso 1 calc . . R
C5 C -0.0024(3) 0.55658(12) 0.29330(18) 0.0391(6) Uani 1 d . . .
H5 H -0.0383 0.5090 0.2935 0.047 Uiso 1 calc . . R
C7 C -0.1370(3) 0.56385(14) 0.08235(19) 0.0394(6) Uani 1 d . . .
C13 C -0.7188(3) 0.29116(14) -0.44413(18) 0.0435(6) Uani 1 d . . .
H13 H -0.7579 0.2439 -0.4539 0.052 Uiso 1 calc . . R
C2 C 0.1085(3) 0.69742(13) 0.29380(18) 0.0414(6) Uani 1 d . . .
H2B H 0.1474 0.7447 0.2937 0.050 Uiso 1 calc . . R
C14 C -0.7535(3) 0.33681(15) -0.53329(19) 0.0492(7) Uani 1 d . . .
H14 H -0.8176 0.3206 -0.6040 0.059 Uiso 1 calc . . R
C16 C -0.6007(3) 0.43380(13) -0.41757(18) 0.0410(6) Uani 1 d . . .
H16 H -0.5619 0.4812 -0.4096 0.049 Uiso 1 calc . . R
C1 C 0.0225(3) 0.66436(13) 0.19453(19) 0.0407(6) Uani 1 d . . .
H1A H 0.0035 0.6897 0.1274 0.049 Uiso 1 calc . . R
C15 C -0.6938(3) 0.40782(15) -0.51965(19) 0.0473(6) Uani 1 d . . .
H15 H -0.7182 0.4380 -0.5818 0.057 Uiso 1 calc . . R


_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
N1 C17 1.373(2) . ?
N1 C9 1.333(3) . ?
N2 N3 1.357(2) . ?
N2 C7 1.373(3) . ?
N3 C8 1.272(3) . ?
C17 C12 1.405(3) . ?
C17 C16 1.402(3) . ?
O1 C7 1.226(3) . ?
C6 C5 1.388(3) . ?
C6 C7 1.483(3) . ?
C6 C1 1.386(3) . ?
O2 C3 1.356(2) . ?
C12 C11 1.401(3) . ?
C12 C13 1.412(3) . ?
C9 C8 1.461(3) . ?
C9 C10 1.392(3) . ?
C11 C10 1.362(3) . ?
C4 C3 1.374(3) . ?
C4 C5 1.381(3) . ?
C3 C2 1.386(3) . ?
C13 C14 1.361(3) . ?
C2 C1 1.374(3) . ?
C14 C15 1.399(3) . ?
C16 C15 1.361(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C17 122.7(2) . . ?
N3 N2 C7 117.42(19) . . ?
C8 N3 N2 118.34(19) . . ?
N1 C17 C12 119.00(19) . . ?
N1 C17 C16 120.2(2) . . ?
C16 C17 C12 120.8(2) . . ?
C5 C6 C7 124.0(2) . . ?
C1 C6 C5 118.4(2) . . ?
C1 C6 C7 117.6(2) . . ?
C17 C12 C13 118.9(2) . . ?
C11 C12 C17 118.03(19) . . ?
C11 C12 C13 123.1(2) . . ?
N1 C9 C8 119.2(2) . . ?
N1 C9 C10 119.49(19) . . ?
C10 C9 C8 121.3(2) . . ?
C10 C11 C12 120.8(2) . . ?
C3 C4 C5 120.1(2) . . ?
O2 C3 C4 122.6(2) . . ?
O2 C3 C2 117.3(2) . . ?
C4 C3 C2 120.1(2) . . ?
N3 C8 C9 118.2(2) . . ?
C11 C10 C9 120.0(2) . . ?
C4 C5 C6 120.6(2) . . ?
N2 C7 C6 116.8(2) . . ?
O1 C7 N2 120.7(2) . . ?
O1 C7 C6 122.5(2) . . ?
C14 C13 C12 119.6(2) . . ?
C1 C2 C3 119.5(2) . . ?
C13 C14 C15 120.7(2) . . ?
C15 C16 C17 118.5(2) . . ?
C2 C1 C6 121.4(2) . . ?
C16 C15 C14 121.6(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_mo_20141208_yf_zz_m1176_0m
_database_code_depnum_ccdc_archive 'CCDC 1500979'
_audit_update_record             
;
2016-08-25 deposited with the CCDC.
2016-11-11 downloaded from the CCDC.
;
_audit_creation_date             2016-08-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C34 H24 Cu N6 O4'
_chemical_formula_sum            'C34 H24 Cu N6 O4'
_chemical_formula_weight         644.13
_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 0.0033 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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   11.839(3)
_cell_length_b                   12.193(4)
_cell_length_c                   13.482(4)
_cell_angle_alpha                70.196(5)
_cell_angle_beta                 80.076(5)
_cell_angle_gamma                61.321(5)
_cell_volume                     1606.3(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1384
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.80
_cell_measurement_theta_min      2.52
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'dark blue'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             662
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0963
_diffrn_reflns_av_unetI/netI     0.1613
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14323
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.61
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                3201
_reflns_number_total             6538
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.608
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         6538
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1699
_refine_ls_R_factor_gt           0.0723
_refine_ls_restrained_S_all      0.970
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0823P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1919
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C33(H33), C27(H27), C5(H5), C34(H34), C25(H25), C10(H10), C16(H16),
 C4(H4A), C2(H2), C17(H17), C30(H30), C7(H7), C13(H13), C31(H31), C14(H14),
 C19(H19), C24(H24), C8(H8), C22(H22), C3(H3A), C20(H20)
2.b Idealised tetrahedral OH refined as rotating group:
 O4(H4), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cu1 Cu 0.61164(7) 0.75915(6) 0.72810(5) 0.0372(2) Uani 1 d . . .
N2 N 0.7727(4) 0.6613(4) 0.8082(3) 0.0356(11) Uani 1 d . . .
N5 N 0.4485(4) 0.8868(4) 0.6551(3) 0.0348(11) Uani 1 d . . .
O1 O 0.7139(4) 0.8760(3) 0.6618(3) 0.0452(10) Uani 1 d . . .
O2 O 0.5022(4) 0.8669(3) 0.8357(3) 0.0445(10) Uani 1 d . . .
O4 O 0.0608(4) 1.3181(4) 1.0161(3) 0.0576(12) Uani 1 d . . .
H4 H 0.0947 1.3077 1.0690 0.086 Uiso 1 calc . . GR
O3 O 1.1208(4) 1.0937(4) 0.6040(4) 0.0570(12) Uani 1 d . . .
H3 H 1.1920 1.0469 0.6310 0.085 Uiso 1 calc . . GR
N6 N 0.3528(4) 0.9736(4) 0.7031(3) 0.0365(11) Uani 1 d . . .
N1 N 0.6054(4) 0.5693(4) 0.8292(3) 0.0392(11) Uani 1 d . . .
N3 N 0.8545(4) 0.7160(4) 0.7948(3) 0.0387(11) Uani 1 d . . .
N4 N 0.6367(4) 0.7062(4) 0.5767(3) 0.0369(11) Uani 1 d . . .
C9 C 0.7076(5) 0.4987(5) 0.8932(4) 0.0405(14) Uani 1 d . . .
C15 C 1.0480(6) 1.0283(6) 0.6360(5) 0.0448(15) Uani 1 d . . .
C26 C 0.5427(5) 0.8018(5) 0.5119(4) 0.0347(13) Uani 1 d . . .
C21 C 0.9288(7) 0.4059(6) 0.4692(6) 0.0651(19) Uani 1 d . . .
H21 H 0.9945 0.3369 0.4469 0.078 Uiso 1 calc . . R
C1 C 0.5211(6) 0.5204(5) 0.8358(4) 0.0414(14) Uani 1 d . . .
C11 C 0.8137(5) 0.8285(5) 0.7141(4) 0.0380(13) Uani 1 d . . .
C28 C 0.3943(5) 0.9539(5) 0.7976(4) 0.0354(13) Uani 1 d . . .
C6 C 0.5358(6) 0.4007(5) 0.9108(4) 0.0464(15) Uani 1 d . . .
C33 C 0.2606(6) 1.1279(6) 1.0075(5) 0.0517(17) Uani 1 d . . .
H33 H 0.2875 1.1200 1.0716 0.062 Uiso 1 calc . . R
C27 C 0.4374(5) 0.8996(5) 0.5577(4) 0.0388(13) Uani 1 d . . .
H27 H 0.3662 0.9675 0.5183 0.047 Uiso 1 calc . . R
C12 C 0.8963(5) 0.8968(5) 0.6898(4) 0.0414(14) Uani 1 d . . .
C29 C 0.3024(5) 1.0479(5) 0.8569(4) 0.0400(14) Uani 1 d . . .
C18 C 0.7332(5) 0.6094(5) 0.5400(4) 0.0405(14) Uani 1 d . . .
C32 C 0.1430(6) 1.2273(6) 0.9677(5) 0.0453(15) Uani 1 d . . .
C5 C 0.4388(7) 0.3601(6) 0.9180(5) 0.0568(17) Uani 1 d . . .
H5 H 0.4454 0.2832 0.9685 0.068 Uiso 1 calc . . R
C23 C 0.7375(6) 0.6101(6) 0.4324(5) 0.0469(15) Uani 1 d . . .
C34 C 0.3384(6) 1.0407(5) 0.9529(4) 0.0462(15) Uani 1 d . . .
H34 H 0.4177 0.9744 0.9809 0.055 Uiso 1 calc . . R
C25 C 0.5382(6) 0.8108(5) 0.4054(4) 0.0453(15) Uani 1 d . . .
H25 H 0.4703 0.8793 0.3627 0.054 Uiso 1 calc . . R
C10 C 0.7967(5) 0.5532(5) 0.8806(4) 0.0404(14) Uani 1 d . . .
H10 H 0.8682 0.5111 0.9235 0.049 Uiso 1 calc . . R
C16 C 0.9299(6) 1.0836(6) 0.5903(6) 0.068(2) Uani 1 d . . .
H16 H 0.9000 1.1660 0.5409 0.081 Uiso 1 calc . . R
C4 C 0.3376(7) 0.4327(7) 0.8519(5) 0.0647(19) Uani 1 d . . .
H4A H 0.2760 0.4045 0.8566 0.078 Uiso 1 calc . . R
C2 C 0.4148(6) 0.5906(6) 0.7689(5) 0.0545(17) Uani 1 d . . .
H2 H 0.4057 0.6679 0.7175 0.065 Uiso 1 calc . . R
C17 C 0.8560(6) 1.0189(6) 0.6167(5) 0.0598(18) Uani 1 d . . .
H17 H 0.7768 1.0583 0.5846 0.072 Uiso 1 calc . . R
C30 C 0.1862(6) 1.1497(7) 0.8173(5) 0.068(2) Uani 1 d . . .
H30 H 0.1611 1.1601 0.7517 0.082 Uiso 1 calc . . R
C7 C 0.6446(6) 0.3275(5) 0.9767(5) 0.0511(16) Uani 1 d . . .
H7 H 0.6575 0.2476 1.0258 0.061 Uiso 1 calc . . R
C13 C 1.0133(6) 0.8423(6) 0.7356(5) 0.0550(17) Uani 1 d . . .
H13 H 1.0428 0.7600 0.7852 0.066 Uiso 1 calc . . R
C31 C 0.1059(7) 1.2365(7) 0.8716(5) 0.075(2) Uani 1 d . . .
H31 H 0.0261 1.3021 0.8440 0.090 Uiso 1 calc . . R
C14 C 1.0888(6) 0.9069(6) 0.7098(5) 0.0576(18) Uani 1 d . . .
H14 H 1.1676 0.8679 0.7425 0.069 Uiso 1 calc . . R
C19 C 0.8306(6) 0.5023(6) 0.6083(5) 0.0544(17) Uani 1 d . . .
H19 H 0.8301 0.4995 0.6781 0.065 Uiso 1 calc . . R
C24 C 0.6362(6) 0.7161(6) 0.3668(5) 0.0564(17) Uani 1 d . . .
H24 H 0.6363 0.7214 0.2963 0.068 Uiso 1 calc . . R
C8 C 0.7293(6) 0.3749(6) 0.9677(5) 0.0511(16) Uani 1 d . . .
H8 H 0.8019 0.3270 1.0099 0.061 Uiso 1 calc . . R
C22 C 0.8389(6) 0.5067(6) 0.3991(5) 0.0562(17) Uani 1 d . . .
H22 H 0.8444 0.5075 0.3292 0.067 Uiso 1 calc . . R
C3 C 0.3247(7) 0.5492(7) 0.7768(5) 0.065(2) Uani 1 d . . .
H3A H 0.2544 0.5988 0.7321 0.078 Uiso 1 calc . . R
C20 C 0.9247(7) 0.4034(6) 0.5732(6) 0.067(2) Uani 1 d . . .
H20 H 0.9874 0.3330 0.6196 0.080 Uiso 1 calc . . R


_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 N2 1.970(4) . ?
Cu1 N5 1.963(4) . ?
Cu1 O1 2.171(4) . ?
Cu1 O2 2.126(4) . ?
Cu1 N1 2.284(4) . ?
Cu1 N4 2.273(4) . ?
N2 N3 1.376(6) . ?
N2 C10 1.278(6) . ?
N5 N6 1.372(6) . ?
N5 C27 1.291(6) . ?
O1 C11 1.257(6) . ?
O2 C28 1.255(6) . ?
O4 C32 1.356(6) . ?
O3 C15 1.366(6) . ?
N6 C28 1.349(6) . ?
N1 C9 1.344(7) . ?
N1 C1 1.365(7) . ?
N3 C11 1.354(6) . ?
N4 C26 1.327(6) . ?
N4 C18 1.360(7) . ?
C9 C10 1.455(8) . ?
C9 C8 1.429(7) . ?
C15 C16 1.377(8) . ?
C15 C14 1.377(8) . ?
C26 C27 1.471(7) . ?
C26 C25 1.412(7) . ?
C21 C22 1.357(8) . ?
C21 C20 1.386(9) . ?
C1 C6 1.414(7) . ?
C1 C2 1.401(8) . ?
C11 C12 1.498(8) . ?
C28 C29 1.504(7) . ?
C6 C5 1.431(8) . ?
C6 C7 1.414(8) . ?
C33 C32 1.376(7) . ?
C33 C34 1.370(8) . ?
C12 C17 1.379(8) . ?
C12 C13 1.369(8) . ?
C29 C34 1.394(7) . ?
C29 C30 1.372(8) . ?
C18 C23 1.440(8) . ?
C18 C19 1.410(7) . ?
C32 C31 1.391(8) . ?
C5 C4 1.353(9) . ?
C23 C24 1.412(8) . ?
C23 C22 1.406(8) . ?
C25 C24 1.365(8) . ?
C16 C17 1.371(8) . ?
C4 C3 1.392(9) . ?
C2 C3 1.358(8) . ?
C30 C31 1.371(8) . ?
C7 C8 1.350(8) . ?
C13 C14 1.387(8) . ?
C19 C20 1.354(8) . ?

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 75.53(16) . . ?
N2 Cu1 O2 95.44(16) . . ?
N2 Cu1 N1 76.45(18) . . ?
N2 Cu1 N4 111.69(17) . . ?
N5 Cu1 N2 168.49(18) . . ?
N5 Cu1 O1 96.92(15) . . ?
N5 Cu1 O2 76.18(17) . . ?
N5 Cu1 N1 111.75(17) . . ?
N5 Cu1 N4 76.80(18) . . ?
O1 Cu1 N1 151.24(15) . . ?
O1 Cu1 N4 91.96(15) . . ?
O2 Cu1 O1 93.87(15) . . ?
O2 Cu1 N1 95.09(15) . . ?
O2 Cu1 N4 152.85(15) . . ?
N4 Cu1 N1 92.40(15) . . ?
N3 N2 Cu1 119.9(3) . . ?
C10 N2 Cu1 121.0(4) . . ?
C10 N2 N3 118.8(4) . . ?
N6 N5 Cu1 119.7(3) . . ?
C27 N5 Cu1 119.9(4) . . ?
C27 N5 N6 119.9(4) . . ?
C11 O1 Cu1 109.9(3) . . ?
C28 O2 Cu1 110.3(3) . . ?
C28 N6 N5 109.0(4) . . ?
C9 N1 Cu1 108.3(4) . . ?
C9 N1 C1 118.8(5) . . ?
C1 N1 Cu1 132.9(4) . . ?
C11 N3 N2 109.7(4) . . ?
C26 N4 Cu1 108.2(3) . . ?
C26 N4 C18 118.7(4) . . ?
C18 N4 Cu1 132.4(4) . . ?
N1 C9 C10 116.5(5) . . ?
N1 C9 C8 121.6(5) . . ?
C8 C9 C10 121.8(5) . . ?
O3 C15 C16 118.9(5) . . ?
O3 C15 C14 123.0(5) . . ?
C14 C15 C16 118.1(6) . . ?
N4 C26 C27 116.3(5) . . ?
N4 C26 C25 123.6(5) . . ?
C25 C26 C27 120.0(5) . . ?
C22 C21 C20 121.4(6) . . ?
N1 C1 C6 121.7(5) . . ?
N1 C1 C2 120.1(5) . . ?
C2 C1 C6 118.1(5) . . ?
O1 C11 N3 124.3(5) . . ?
O1 C11 C12 120.6(5) . . ?
N3 C11 C12 115.1(5) . . ?
O2 C28 N6 124.7(5) . . ?
O2 C28 C29 120.1(5) . . ?
N6 C28 C29 115.2(5) . . ?
C1 C6 C5 118.6(6) . . ?
C1 C6 C7 118.5(5) . . ?
C7 C6 C5 122.8(5) . . ?
C34 C33 C32 120.2(5) . . ?
N5 C27 C26 116.8(5) . . ?
C17 C12 C11 119.6(5) . . ?
C13 C12 C11 122.9(5) . . ?
C13 C12 C17 117.4(5) . . ?
C34 C29 C28 119.9(5) . . ?
C30 C29 C28 123.1(5) . . ?
C30 C29 C34 116.8(5) . . ?
N4 C18 C23 121.7(5) . . ?
N4 C18 C19 120.3(5) . . ?
C19 C18 C23 117.9(5) . . ?
O4 C32 C33 124.0(5) . . ?
O4 C32 C31 117.6(5) . . ?
C33 C32 C31 118.5(6) . . ?
C4 C5 C6 120.5(6) . . ?
C24 C23 C18 116.7(5) . . ?
C22 C23 C18 119.3(6) . . ?
C22 C23 C24 124.0(6) . . ?
C33 C34 C29 122.1(5) . . ?
C24 C25 C26 118.2(5) . . ?
N2 C10 C9 117.3(5) . . ?
C17 C16 C15 120.9(6) . . ?
C5 C4 C3 120.7(6) . . ?
C3 C2 C1 122.0(6) . . ?
C16 C17 C12 121.6(6) . . ?
C31 C30 C29 121.9(6) . . ?
C8 C7 C6 119.2(5) . . ?
C12 C13 C14 121.6(6) . . ?
C30 C31 C32 120.5(6) . . ?
C15 C14 C13 120.4(6) . . ?
C20 C19 C18 120.7(6) . . ?
C25 C24 C23 120.9(5) . . ?
C7 C8 C9 120.0(6) . . ?
C21 C22 C23 119.8(6) . . ?
C2 C3 C4 120.0(6) . . ?
C19 C20 C21 120.9(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
