# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1
_audit_creation_date             2012-10-18
_audit_creation_method           
;
  Olex2 1.2
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H9 Cu N3 O3'
_chemical_formula_sum            'C10 H9 Cu N3 O3'
_chemical_formula_weight         282.74
_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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y+3/4, x+1/4, z+1/4'
3 '-x, -y+1/2, z'
4 'y+1/4, -x+1/4, z+1/4'
5 'x+1/2, y+1/2, z+1/2'
6 '-y+5/4, x+3/4, z+3/4'
7 '-x+1/2, -y+1, z+1/2'
8 'y+3/4, -x+3/4, z+3/4'
9 '-x, -y, -z'
10 'y-3/4, -x-1/4, -z-1/4'
11 'x, y-1/2, -z'
12 '-y-1/4, x-1/4, -z-1/4'
13 '-x+1/2, -y+1/2, -z+1/2'
14 'y-1/4, -x+1/4, -z+1/4'
15 'x+1/2, y, -z+1/2'
16 '-y+1/4, x+1/4, -z+1/4'

_cell_length_a                   16.6545(16)
_cell_length_b                   16.6545(16)
_cell_length_c                   16.3362(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4531.2(8)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    890
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      20.37
_cell_measurement_theta_min      3.01
_exptl_absorpt_coefficient_mu    1.927
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0858 before and 0.0632 after correction.
The Ratio of minimum to maximum transmission is 0.7979.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9990
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         3.01
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_number_gt                1320
_reflns_number_total             1998
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         1998
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0462P)²+3.5502P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.1097
_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. 
;
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.30216(4) 0.28587(4) 0.85067(3) 0.0260(2) Uani 1 1 d . . .
O12 O 0.39957(19) 0.35240(19) 0.86181(19) 0.0308(8) Uani 1 1 d . . .
O13 O 0.33119(19) 0.24014(18) 0.96081(19) 0.0266(8) Uani 1 1 d . . .
O14 O 0.2374(2) 0.38928(19) 0.9122(2) 0.0373(9) Uani 1 1 d . . .
N2 N 0.2035(2) 0.2258(2) 0.8415(2) 0.0242(9) Uani 1 1 d . . .
N10 N 0.3250(2) 0.3015(2) 0.7316(2) 0.0245(9) Uani 1 1 d . . .
C8 C 0.4101(3) 0.3467(3) 0.6370(3) 0.0273(12) Uani 1 1 d . . .
C11 C 0.4303(3) 0.3735(3) 0.7946(3) 0.0231(11) Uani 1 1 d . . .
C9 C 0.3919(3) 0.3434(3) 0.7202(3) 0.0252(11) Uani 1 1 d . . .
C3 C 0.1513(3) 0.1991(3) 0.9004(3) 0.0261(11) Uani 1 1 d . . .
C7 C 0.4716(3) 0.3815(3) 0.5885(3) 0.0378(13) Uani 1 1 d . . .
H7 H 0.5119 0.4122 0.6125 0.045 Uiso 1 1 calc R . .
C6 C 0.4704(3) 0.3689(3) 0.5061(3) 0.0416(14) Uani 1 1 d . . .
H6 H 0.5101 0.3915 0.4733 0.050 Uiso 1 1 calc R . .
C4 C 0.1514(3) 0.2124(3) 0.9857(3) 0.0359(13) Uani 1 1 d . . .
H4 H 0.1912 0.2432 1.0106 0.043 Uiso 1 1 calc R . .
C5 C 0.4088(3) 0.3215(3) 0.4697(3) 0.0413(14) Uani 1 1 d . . .
H5 H 0.4097 0.3133 0.4134 0.050 Uiso 1 1 calc R . .
C15 C 0.2565(3) 0.4257(3) 0.9768(3) 0.0338(13) Uani 1 1 d . . .
N16 N 0.3130(3) 0.3992(3) 1.0260(3) 0.0465(13) Uani 1 1 d D . .
H16A H 0.324(3) 0.429(3) 1.075(2) 0.056 Uiso 1 1 d D . .
H16B H 0.342(3) 0.351(2) 1.015(3) 0.056 Uiso 1 1 d D . .
C17 C 0.2170(4) 0.5024(4) 0.9986(4) 0.080(2) Uani 1 1 d . . .
H17A H 0.2346 0.5438 0.9618 0.120 Uiso 1 1 calc R . .
H17B H 0.2309 0.5169 1.0537 0.120 Uiso 1 1 calc R . .
H17C H 0.1598 0.4964 0.9943 0.120 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0332(4) 0.0303(4) 0.0144(3) 0.0001(3) -0.0062(3) -0.0032(3)
O12 0.037(2) 0.040(2) 0.0149(18) -0.0018(16) 0.0013(16) -0.0062(17)
O13 0.033(2) 0.0265(19) 0.0202(18) 0.0013(15) -0.0079(15) 0.0026(17)
O14 0.046(2) 0.036(2) 0.030(2) -0.0074(17) -0.0139(18) 0.0088(17)
N2 0.030(2) 0.027(2) 0.015(2) -0.0009(18) -0.0021(18) -0.0013(19)
N10 0.032(2) 0.027(2) 0.015(2) -0.0008(17) -0.0053(18) -0.0033(19)
C8 0.026(3) 0.035(3) 0.021(3) -0.005(2) -0.002(2) 0.005(2)
C11 0.026(3) 0.021(3) 0.022(3) -0.003(2) -0.003(2) 0.002(2)
C9 0.033(3) 0.028(3) 0.015(3) -0.002(2) -0.002(2) 0.001(2)
C3 0.028(3) 0.028(3) 0.022(3) -0.004(2) -0.003(2) -0.001(2)
C7 0.042(3) 0.045(3) 0.027(3) -0.012(3) 0.000(3) -0.003(3)
C6 0.040(3) 0.060(4) 0.025(3) -0.003(3) 0.009(3) -0.009(3)
C4 0.044(3) 0.045(3) 0.019(3) -0.005(2) -0.004(3) -0.003(3)
C5 0.051(4) 0.054(4) 0.018(3) -0.012(3) -0.001(3) -0.003(3)
C15 0.042(3) 0.032(3) 0.028(3) 0.000(2) -0.007(3) 0.003(3)
N16 0.063(3) 0.042(3) 0.034(3) -0.012(2) -0.021(3) 0.013(3)
C17 0.095(6) 0.078(5) 0.068(5) -0.039(4) -0.039(4) 0.046(4)

_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 O12 1.973(3) . ?
Cu1 O13 2.013(3) . ?
Cu1 O14 2.267(3) . ?
Cu1 N2 1.930(4) . ?
Cu1 N10 1.999(4) . ?
O12 C11 1.262(5) . ?
O13 C11 1.254(5) 12_657 ?
O14 C15 1.258(6) . ?
N2 N10 1.362(5) 13_556 ?
N2 C3 1.371(6) . ?
N10 N2 1.362(5) 13_556 ?
N10 C9 1.328(6) . ?
C8 C9 1.394(6) . ?
C8 C3 1.416(6) 13_556 ?
C8 C7 1.418(7) . ?
C11 O13 1.254(5) 10_667 ?
C11 C9 1.461(6) . ?
C3 C8 1.416(6) 13_556 ?
C3 C4 1.410(7) . ?
C7 H7 0.9300 . ?
C7 C6 1.364(7) . ?
C6 H6 0.9300 . ?
C6 C5 1.425(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.362(7) 13_556 ?
C5 C4 1.362(7) 13_556 ?
C5 H5 0.9300 . ?
C15 N16 1.314(6) . ?
C15 C17 1.480(7) . ?
N16 H16A 0.97(2) . ?
N16 H16B 0.958(19) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
O12 Cu1 O13 86.14(13) . . ?
O12 Cu1 O14 85.60(13) . . ?
O12 Cu1 N10 81.96(14) . . ?
O13 Cu1 O14 90.29(13) . . ?
N2 Cu1 O12 176.91(15) . . ?
N2 Cu1 O13 94.46(14) . . ?
N2 Cu1 O14 91.36(14) . . ?
N2 Cu1 N10 98.85(15) . . ?
N10 Cu1 O13 150.87(14) . . ?
N10 Cu1 O14 115.03(14) . . ?
C11 O12 Cu1 114.2(3) . . ?
C11 O13 Cu1 112.5(3) 12_657 . ?
C15 O14 Cu1 128.2(3) . . ?
N10 N2 Cu1 122.5(3) 13_556 . ?
N10 N2 C3 106.7(4) 13_556 . ?
C3 N2 Cu1 130.7(3) . . ?
N2 N10 Cu1 138.0(3) 13_556 . ?
C9 N10 Cu1 111.4(3) . . ?
C9 N10 N2 110.2(4) . 13_556 ?
C9 C8 C3 104.0(4) . 13_556 ?
C9 C8 C7 135.9(5) . . ?
C3 C8 C7 120.1(4) 13_556 . ?
O12 C11 C9 116.8(4) . . ?
O13 C11 O12 123.4(4) 10_667 . ?
O13 C11 C9 119.7(4) 10_667 . ?
N10 C9 C8 109.9(4) . . ?
N10 C9 C11 115.5(4) . . ?
C8 C9 C11 134.6(5) . . ?
N2 C3 C8 109.2(4) . 13_556 ?
N2 C3 C4 130.0(4) . . ?
C4 C3 C8 120.8(5) . 13_556 ?
C8 C7 H7 120.7 . . ?
C6 C7 C8 118.6(5) . . ?
C6 C7 H7 120.7 . . ?
C7 C6 H6 119.8 . . ?
C7 C6 C5 120.5(5) . . ?
C5 C6 H6 119.8 . . ?
C3 C4 H4 121.2 . . ?
C5 C4 C3 117.5(5) 13_556 . ?
C5 C4 H4 121.2 13_556 . ?
C6 C5 H5 118.7 . . ?
C4 C5 C6 122.5(5) 13_556 . ?
C4 C5 H5 118.7 13_556 . ?
O14 C15 N16 122.1(5) . . ?
O14 C15 C17 120.4(5) . . ?
N16 C15 C17 117.5(5) . . ?
C15 N16 H16A 118(3) . . ?
C15 N16 H16B 122(3) . . ?
H16A N16 H16B 120(5) . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
N16 H16A O14 0.97(2) 1.83(2) 2.783(5) 170(5) 2
N16 H16B O13 0.958(19) 2.05(4) 2.871(6) 142(4) .
_database_code_depnum_ccdc_archive 'CCDC 983017'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2
_audit_creation_date             2012-10-18
_audit_creation_method           
;
  Olex2 1.2
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C9 H11 Cu N3 O3'
_chemical_formula_sum            'C9 H11 Cu N3 O3'
_chemical_formula_weight         272.75
_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'
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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-y+3/4, x+1/4, z+1/4'
3 '-x, -y+1/2, z'
4 'y+1/4, -x+1/4, z+1/4'
5 'x+1/2, y+1/2, z+1/2'
6 '-y+5/4, x+3/4, z+3/4'
7 '-x+1/2, -y+1, z+1/2'
8 'y+3/4, -x+3/4, z+3/4'
9 '-x, -y, -z'
10 'y-3/4, -x-1/4, -z-1/4'
11 'x, y-1/2, -z'
12 '-y-1/4, x-1/4, -z-1/4'
13 '-x+1/2, -y+1/2, -z+1/2'
14 'y-1/4, -x+1/4, -z+1/4'
15 'x+1/2, y, -z+1/2'
16 '-y+1/4, x+1/4, -z+1/4'

_cell_length_a                   18.0584(8)
_cell_length_b                   18.0584(8)
_cell_length_c                   18.3413(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5981.2(5)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      30.40
_cell_measurement_theta_min      2.26
_exptl_absorpt_coefficient_mu    1.457
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0815 before and 0.0618 after correction.
The Ratio of minimum to maximum transmission is 0.8503.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2224
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            36629
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.58
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_number_gt                2497
_reflns_number_total             2647
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.53A (Bruker, 2008)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         1.043
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2647
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0651
_refine_ls_restrained_S_all      1.206
_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)+(0.0573P)²+73.8951P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1589
_refine_ls_wR_factor_ref         0.1620
_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. 
;
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.19358(3) 0.74298(3) 0.34219(3) 0.0126(2) Uani 1 1 d . . .
O8 O 0.1116(2) 0.6715(2) 0.36704(18) 0.0167(8) Uani 1 1 d . . .
O9 O 0.17325(19) 0.79845(19) 0.43098(19) 0.0156(8) Uani 1 1 d . . .
N6 N 0.1949(2) 0.6861(2) 0.2512(2) 0.0128(9) Uani 1 1 d . . .
N2 N 0.2675(2) 0.8171(2) 0.3123(2) 0.0149(9) Uani 1 1 d . . .
O10 O 0.2837(2) 0.6762(2) 0.4056(2) 0.0307(10) Uani 1 1 d . . .
C7 C 0.0969(3) 0.6267(3) 0.3170(3) 0.0138(10) Uani 1 1 d . . .
C4 C 0.3531(3) 0.9074(3) 0.3151(3) 0.0215(12) Uani 1 1 d . . .
H4 H 0.3818 0.9473 0.3300 0.026 Uiso 1 1 calc R . .
C3 C 0.2966(3) 0.8730(3) 0.3526(3) 0.0221(12) Uani 1 1 d . . .
H3 H 0.2807 0.8863 0.3990 0.026 Uiso 1 1 calc R . .
C5 C 0.1428(3) 0.6318(3) 0.2506(3) 0.0154(11) Uani 1 1 d . . .
N12 N 0.3493(4) 0.5973(4) 0.3359(4) 0.061(2) Uani 1 1 d . . .
C11 C 0.3377(4) 0.6553(5) 0.3712(3) 0.048(2) Uani 1 1 d . . .
C15 C 0.4094(4) 0.7023(5) 0.3628(4) 0.0448(18) Uani 1 1 d . . .
H15A H 0.3977 0.7533 0.3511 0.054 Uiso 1 1 calc R . .
H15B H 0.4386 0.7012 0.4072 0.054 Uiso 1 1 calc R . .
C14 C 0.4487(5) 0.6672(5) 0.3035(5) 0.058(2) Uani 1 1 d . . .
H14A H 0.5016 0.6670 0.3128 0.070 Uiso 1 1 calc R . .
H14B H 0.4395 0.6931 0.2581 0.070 Uiso 1 1 calc R . .
C13 C 0.4171(5) 0.5834(5) 0.2994(4) 0.058(2) Uani 1 1 d . . .
H13A H 0.4098 0.5667 0.2497 0.070 Uiso 1 1 calc R . .
H13B H 0.4482 0.5485 0.3255 0.070 Uiso 1 1 calc R . .
C16 C 0.2923(5) 0.5372(5) 0.3382(7) 0.072(3) Uani 1 1 d . . .
H16A H 0.2665 0.5391 0.3839 0.108 Uiso 1 1 calc R . .
H16B H 0.3162 0.4900 0.3332 0.108 Uiso 1 1 calc R . .
H16C H 0.2578 0.5440 0.2990 0.108 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0139(4) 0.0143(4) 0.0097(3) -0.0017(2) 0.0035(2) -0.0013(2)
O8 0.0202(19) 0.0197(19) 0.0101(17) 0.0003(15) 0.0048(14) -0.0023(15)
O9 0.0159(18) 0.0180(19) 0.0129(17) -0.0020(14) 0.0043(14) 0.0038(14)
N6 0.015(2) 0.014(2) 0.010(2) 0.0003(16) 0.0053(17) -0.0004(16)
N2 0.016(2) 0.018(2) 0.010(2) -0.0065(17) 0.0032(17) -0.0015(17)
O10 0.022(2) 0.043(3) 0.027(2) 0.0088(19) 0.0043(18) 0.0137(19)
C7 0.010(2) 0.017(3) 0.015(3) 0.003(2) 0.0000(19) 0.004(2)
C4 0.026(3) 0.017(3) 0.022(3) -0.009(2) 0.007(2) -0.009(2)
C3 0.028(3) 0.027(3) 0.011(3) -0.003(2) 0.007(2) -0.004(2)
C5 0.020(3) 0.014(3) 0.012(2) 0.003(2) 0.004(2) -0.003(2)
N12 0.079(5) 0.069(5) 0.035(4) -0.002(3) -0.001(3) 0.030(4)
C11 0.041(4) 0.091(6) 0.012(3) 0.003(4) -0.005(3) 0.030(4)
C15 0.034(4) 0.056(5) 0.044(4) 0.003(4) -0.006(3) 0.001(3)
C14 0.043(5) 0.074(6) 0.057(5) -0.004(5) -0.006(4) -0.014(4)
C13 0.048(5) 0.093(7) 0.034(4) -0.022(4) 0.001(3) 0.020(5)
C16 0.055(5) 0.040(5) 0.120(9) 0.020(5) -0.021(6) -0.020(4)

_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 O8 2.016(4) . ?
Cu1 O9 1.947(3) . ?
Cu1 N6 1.960(4) . ?
Cu1 N2 1.968(4) . ?
Cu1 O10 2.337(4) . ?
O8 C7 1.251(6) . ?
O9 C7 1.258(6) 12_666 ?
N6 N2 1.350(6) 13_565 ?
N6 C5 1.358(7) . ?
N2 N6 1.350(6) 13_565 ?
N2 C3 1.357(7) . ?
O10 C11 1.222(8) . ?
C7 O9 1.258(6) 10_566 ?
C7 C5 1.476(7) . ?
C4 H4 0.9300 . ?
C4 C3 1.378(8) . ?
C4 C5 1.399(7) 13_565 ?
C3 H3 0.9300 . ?
C5 C4 1.399(7) 13_565 ?
N12 C11 1.250(11) . ?
N12 C13 1.419(10) . ?
N12 C16 1.494(11) . ?
C11 C15 1.556(11) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.445(12) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.618(13) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
O8 Cu1 O10 93.90(15) . . ?
O9 Cu1 O8 90.11(14) . . ?
O9 Cu1 N6 169.84(16) . . ?
O9 Cu1 N2 90.62(16) . . ?
O9 Cu1 O10 88.87(15) . . ?
N6 Cu1 O8 82.27(15) . . ?
N6 Cu1 N2 96.40(17) . . ?
N6 Cu1 O10 98.31(16) . . ?
N2 Cu1 O8 175.03(17) . . ?
N2 Cu1 O10 91.03(17) . . ?
C7 O8 Cu1 113.8(3) . . ?
C7 O9 Cu1 121.2(3) 12_666 . ?
N2 N6 Cu1 139.7(3) 13_565 . ?
N2 N6 C5 108.1(4) 13_565 . ?
C5 N6 Cu1 112.1(3) . . ?
N6 N2 Cu1 123.6(3) 13_565 . ?
N6 N2 C3 107.8(4) 13_565 . ?
C3 N2 Cu1 128.1(3) . . ?
C11 O10 Cu1 117.2(4) . . ?
O8 C7 O9 126.2(5) . 10_566 ?
O8 C7 C5 116.5(4) . . ?
O9 C7 C5 117.3(5) 10_566 . ?
C3 C4 H4 128.0 . . ?
C3 C4 C5 104.0(5) . 13_565 ?
C5 C4 H4 128.0 13_565 . ?
N2 C3 C4 110.5(5) . . ?
N2 C3 H3 124.8 . . ?
C4 C3 H3 124.8 . . ?
N6 C5 C7 115.3(4) . . ?
N6 C5 C4 109.5(4) . 13_565 ?
C4 C5 C7 135.2(5) 13_565 . ?
C11 N12 C13 122.4(9) . . ?
C11 N12 C16 118.7(8) . . ?
C13 N12 C16 118.6(8) . . ?
O10 C11 N12 131.2(9) . . ?
O10 C11 C15 123.3(8) . . ?
N12 C11 C15 105.5(7) . . ?
C11 C15 H15A 110.9 . . ?
C11 C15 H15B 110.9 . . ?
H15A C15 H15B 109.0 . . ?
C14 C15 C11 104.1(6) . . ?
C14 C15 H15A 110.9 . . ?
C14 C15 H15B 110.9 . . ?
C15 C14 H14A 110.6 . . ?
C15 C14 H14B 110.6 . . ?
C15 C14 C13 105.8(7) . . ?
H14A C14 H14B 108.7 . . ?
C13 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
N12 C13 C14 96.8(7) . . ?
N12 C13 H13A 112.4 . . ?
N12 C13 H13B 112.4 . . ?
C14 C13 H13A 112.4 . . ?
C14 C13 H13B 112.4 . . ?
H13A C13 H13B 110.0 . . ?
N12 C16 H16A 109.5 . . ?
N12 C16 H16B 109.5 . . ?
N12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O8 C7 O9 179.9(4) . . . 10_566 ?
Cu1 O8 C7 C5 2.1(5) . . . . ?
Cu1 N6 C5 C7 -0.1(5) . . . . ?
Cu1 N6 C5 C4 -179.4(4) . . . 13_565 ?
Cu1 N2 C3 C4 172.8(4) . . . . ?
Cu1 O10 C11 N12 -89.1(9) . . . . ?
Cu1 O10 C11 C15 89.8(7) . . . . ?
O8 Cu1 O9 C7 -84.1(4) . . . 12_666 ?
O8 Cu1 N6 N2 -178.1(5) . . . 13_565 ?
O8 Cu1 N6 C5 0.9(3) . . . . ?
O8 Cu1 N2 N6 -79.4(19) . . . 13_565 ?
O8 Cu1 N2 C3 109.7(18) . . . . ?
O8 Cu1 O10 C11 122.4(6) . . . . ?
O8 C7 C5 N6 -1.4(7) . . . . ?
O8 C7 C5 C4 177.7(6) . . . 13_565 ?
O9 Cu1 O8 C7 171.6(3) . . . . ?
O9 Cu1 N6 N2 140.1(8) . . . 13_565 ?
O9 Cu1 N6 C5 -40.9(11) . . . . ?
O9 Cu1 N2 N6 -177.9(4) . . . 13_565 ?
O9 Cu1 N2 C3 11.2(5) . . . . ?
O9 Cu1 O10 C11 -147.6(6) . . . . ?
O9 C7 C5 N6 -179.4(4) 10_566 . . . ?
O9 C7 C5 C4 -0.3(9) 10_566 . . 13_565 ?
N6 Cu1 O8 C7 -1.7(3) . . . . ?
N6 Cu1 O9 C7 -42.7(11) . . . 12_666 ?
N6 Cu1 N2 N6 -5.2(5) . . . 13_565 ?
N6 Cu1 N2 C3 -176.1(5) . . . . ?
N6 Cu1 O10 C11 39.6(6) . . . . ?
N6 N2 C3 C4 0.7(6) 13_565 . . . ?
N2 Cu1 O8 C7 73.1(19) . . . . ?
N2 Cu1 O9 C7 91.0(4) . . . 12_666 ?
N2 Cu1 N6 N2 6.7(6) . . . 13_565 ?
N2 Cu1 N6 C5 -174.3(4) . . . . ?
N2 Cu1 O10 C11 -57.0(6) . . . . ?
N2 N6 C5 C7 179.2(4) 13_565 . . . ?
N2 N6 C5 C4 -0.1(6) 13_565 . . 13_565 ?
O10 Cu1 O8 C7 -99.6(3) . . . . ?
O10 Cu1 O9 C7 -178.0(4) . . . 12_666 ?
O10 Cu1 N6 N2 -85.2(5) . . . 13_565 ?
O10 Cu1 N6 C5 93.7(4) . . . . ?
O10 Cu1 N2 N6 93.3(4) . . . 13_565 ?
O10 Cu1 N2 C3 -77.7(5) . . . . ?
O10 C11 C15 C14 -164.7(7) . . . . ?
C5 C4 C3 N2 -0.6(7) 13_565 . . . ?
N12 C11 C15 C14 14.4(8) . . . . ?
C11 N12 C13 C14 -14.2(9) . . . . ?
C11 C15 C14 C13 -22.1(8) . . . . ?
C15 C14 C13 N12 21.6(8) . . . . ?
C13 N12 C11 O10 -179.8(7) . . . . ?
C13 N12 C11 C15 1.2(10) . . . . ?
C16 N12 C11 O10 -5.8(12) . . . . ?
C16 N12 C11 C15 175.1(7) . . . . ?
C16 N12 C13 C14 171.8(7) . . . . ?

_platon_squeeze_details          
;
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.013 -0.002 -0.001 2142 1230 ' '

_database_code_depnum_ccdc_archive 'CCDC 983018'
