# 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 2017

####################################################################### 
# 
# 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_CuTECP
_database_code_depnum_ccdc_archive 'CCDC 1504785'
_audit_update_record             
;
2016-09-18 deposited with the CCDC.
2017-03-29 downloaded from the CCDC.
;
_audit_creation_date             2014-11-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4957)
;
_chemical_name_common            CuTECP
_chemical_name_systematic        
'5,10,15,20-tetra-(ethoxylcarbonyl)porphyrin copper(II)'
_chemical_formula_moiety         'C32 H28 Cu N4 O8'
_chemical_formula_sum            'C32 H28 Cu N4 O8'
_chemical_formula_weight         660.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.4200(5)
_cell_length_b                   8.6707(7)
_cell_length_c                   12.9072(10)
_cell_angle_alpha                85.110(7)
_cell_angle_beta                 88.215(6)
_cell_angle_gamma                83.692(6)
_cell_volume                     711.37(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3201
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      62.3540
_cell_measurement_theta_min      5.9330
_exptl_absorpt_coefficient_mu    1.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             341
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6928
_diffrn_reflns_theta_full        62.51
_diffrn_reflns_theta_max         62.51
_diffrn_reflns_theta_min         5.96
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0855
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -106.00  -56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -34.2729 -179.0000  -30.0000 50

#__ type_ start__ end____ width___ exp.time_
  2 omega -111.00  -73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -34.2729  179.0000   90.0000 38

#__ type_ start__ end____ width___ exp.time_
  3 omega -110.00  -77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -34.2729 -179.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
  4 omega   36.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.2729  179.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  -39.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.2729  -19.0000  150.0000 110

#__ type_ start__ end____ width___ exp.time_
  6 omega   19.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.2729   57.0000  -30.0000 73

#__ type_ start__ end____ width___ exp.time_
  7 omega   84.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500   30.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
  8 omega   26.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -30.0000 -180.0000 42

#__ type_ start__ end____ width___ exp.time_
  9 omega   84.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -92.0000 -130.6309 38

#__ type_ start__ end____ width___ exp.time_
 10 omega   96.00  134.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  179.0000  -90.0000 38

#__ type_ start__ end____ width___ exp.time_
 11 omega   24.00   73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500 -111.0000 -120.0000 49

#__ type_ start__ end____ width___ exp.time_
 12 omega  119.00  153.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500   61.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
 13 omega   23.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -94.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
 14 omega   19.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500 -111.0000   60.0000 56

#__ type_ start__ end____ width___ exp.time_
 15 omega   42.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  179.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
 16 omega   83.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -92.0000   58.5368 27

#__ type_ start__ end____ width___ exp.time_
 17 omega   50.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -77.0000   60.0000 56

#__ type_ start__ end____ width___ exp.time_
 18 omega   72.00  162.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500   30.0000 -150.0000 90

#__ type_ start__ end____ width___ exp.time_
 19 omega   68.00  147.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500   77.0000  -90.0000 79

#__ type_ start__ end____ width___ exp.time_
 20 omega   33.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500 -111.0000   30.0000 44

#__ type_ start__ end____ width___ exp.time_
 21 omega  132.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500   30.0000  120.0000 31

#__ type_ start__ end____ width___ exp.time_
 22 omega   56.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  179.0000    0.0000 38

#__ type_ start__ end____ width___ exp.time_
 23 omega   78.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -93.0000  154.7851 51

#__ type_ start__ end____ width___ exp.time_
 24 omega   70.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500   61.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
 25 omega   86.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -92.0000  -55.8673 25

#__ type_ start__ end____ width___ exp.time_
 26 omega   29.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -30.0000    0.0000 40

#__ type_ start__ end____ width___ exp.time_
 27 omega   35.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500 -111.0000  150.0000 31

#__ type_ start__ end____ width___ exp.time_
 28 omega   58.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500 -125.0000  112.0000 38

#__ type_ start__ end____ width___ exp.time_
 29 omega   78.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500   45.0000    0.0000 40

#__ type_ start__ end____ width___ exp.time_
 30 omega   34.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -92.0000  -55.8673 27

#__ type_ start__ end____ width___ exp.time_
 31 omega    4.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.2729   77.0000   60.0000 100

#__ type_ start__ end____ width___ exp.time_
 32 omega   32.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.2729 -179.0000   60.0000 79

#__ type_ start__ end____ width___ exp.time_
 33 omega    4.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.2729   77.0000 -180.0000 100

#__ type_ start__ end____ width___ exp.time_
 34 omega    4.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.2729   77.0000    0.0000 100

#__ type_ start__ end____ width___ exp.time_
 35 omega   14.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.2729   57.0000  150.0000 89

#__ type_ start__ end____ width___ exp.time_
 36 omega   14.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       34.2729   57.0000  -90.0000 89

#__ type_ start__ end____ width___ exp.time_
 37 omega   69.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500   61.0000   30.0000 89

#__ type_ start__ end____ width___ exp.time_
 38 omega   67.00  139.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500   45.0000   90.0000 72

#__ type_ start__ end____ width___ exp.time_
 39 omega   18.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500  -30.0000  120.0000 51

#__ type_ start__ end____ width___ exp.time_
 40 omega   69.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.3500   61.0000 -120.0000 89
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0276972000
_diffrn_orient_matrix_UB_12      -0.0723538000
_diffrn_orient_matrix_UB_13      -0.1051656000
_diffrn_orient_matrix_UB_21      0.0053907000
_diffrn_orient_matrix_UB_22      -0.1639586000
_diffrn_orient_matrix_UB_23      0.0568325000
_diffrn_orient_matrix_UB_31      -0.2398279000
_diffrn_orient_matrix_UB_32      0.0074038000
_diffrn_orient_matrix_UB_33      -0.0082143000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2012
_reflns_number_total             2249
_reflns_odcompleteness_completeness 88.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.041
_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)+(0.0491P)²+0.5628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1016
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C15(H15A,H15B)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O4 O 0.3125(3) 0.8246(2) 0.40760(13) 0.0290(4) Uani 1 d . . 1 . . .
O2 O 1.1771(3) 0.5648(2) 0.12819(14) 0.0323(5) Uani 1 d . . 1 . . .
N1 N 0.7414(3) 0.9133(2) -0.08822(15) 0.0219(5) Uani 1 d . . 1 . . .
O1 O 1.3451(3) 0.7333(2) 0.02434(14) 0.0279(4) Uani 1 d . . 1 . . .
O3 O 0.2929(3) 1.0806(2) 0.42811(13) 0.0319(5) Uani 1 d . . 1 . . .
N2 N 0.6530(3) 0.9056(2) 0.12917(16) 0.0220(5) Uani 1 d . . 1 . . .
C14 C 1.1859(4) 0.6943(3) 0.06534(19) 0.0240(6) Uani 1 d . . 1 . . .
C9 C 0.5818(4) 0.9115(3) 0.23001(19) 0.0236(5) Uani 1 d . . 1 . . .
C8 C 0.7356(4) 0.8326(3) 0.3003(2) 0.0274(6) Uani 1 d . . 1 . . .
C5 C 0.9741(4) 0.7839(3) 0.04860(19) 0.0219(5) Uani 1 d . . 1 . . .
C10 C 0.3890(4) 0.9867(3) 0.26050(19) 0.0229(5) Uani 1 d . . 1 . . .
C7 C 0.8982(4) 0.7764(3) 0.2424(2) 0.0269(6) Uani 1 d . . 1 . . .
C6 C 0.8467(4) 0.8196(3) 0.13459(19) 0.0229(5) Uani 1 d . . 1 . . .
C12 C 0.2446(5) 0.7948(3) 0.5158(2) 0.0355(7) Uani 1 d . . 1 . . .
H12A H 0.1290 0.8707 0.5330 0.043 Uiso 1 calc . . 1 R . .
H12B H 0.3590 0.8017 0.5620 0.043 Uiso 1 calc . . 1 R . .
C4 C 0.9243(4) 0.8287(3) -0.05487(19) 0.0227(5) Uani 1 d . . 1 . . .
C2 C 0.9549(4) 0.8527(3) -0.2289(2) 0.0275(6) Uani 1 d . . 1 . . .
C16 C 1.4091(6) 0.4599(5) 0.2653(3) 0.0621(11) Uani 1 d . . 1 . . .
H16A H 1.5374 0.3954 0.2809 0.093 Uiso 1 calc . . 1 GR . .
H16B H 1.2942 0.4148 0.3011 0.093 Uiso 1 calc . . 1 GR . .
H16C H 1.4173 0.5619 0.2875 0.093 Uiso 1 calc . . 1 GR . .
C3 C 1.0554(4) 0.7900(3) -0.1436(2) 0.0274(6) Uani 1 d . . 1 . . .
C11 C 0.3286(4) 0.9731(3) 0.37424(19) 0.0250(6) Uani 1 d . . 1 . . .
C15 C 1.3758(5) 0.4715(3) 0.1522(2) 0.0373(7) Uani 1 d . . 1 . . .
H15A H 1.4898 0.5194 0.1159 0.045 Uiso 1 calc . . 1 R . .
H15B H 1.3740 0.3682 0.1290 0.045 Uiso 1 calc . . 1 R . .
C13 C 0.1778(6) 0.6364(4) 0.5273(3) 0.0514(9) Uani 1 d . . 1 . . .
H13A H 0.0711 0.6291 0.4780 0.077 Uiso 1 calc . . 1 GR . .
H13B H 0.1230 0.6156 0.5965 0.077 Uiso 1 calc . . 1 GR . .
H13C H 0.2958 0.5618 0.5148 0.077 Uiso 1 calc . . 1 GR . .
Cu1 Cu 0.5000 1.0000 0.0000 0.02056(18) Uani 1 d . . 2 S T P
C1 C 0.7584(4) 0.9302(3) -0.19456(19) 0.0227(5) Uani 1 d . . 1 . . .
H7 H 1.020(4) 0.722(3) 0.265(2) 0.024(7) Uiso 1 d . . 1 . . .
H2 H 1.000(4) 0.851(3) -0.296(2) 0.024(7) Uiso 1 d . . 1 . . .
H3 H 1.182(5) 0.733(3) -0.137(2) 0.029(7) Uiso 1 d . . 1 . . .
H8 H 0.723(4) 0.830(3) 0.373(2) 0.034(8) Uiso 1 d . . 1 . . .


_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
O4 C12 1.461(3) . ?
O4 C11 1.336(3) . ?
O2 C14 1.333(3) . ?
O2 C15 1.460(3) . ?
N1 C4 1.375(3) . ?
N1 Cu1 2.011(2) . ?
N1 C1 1.370(3) . ?
O1 C14 1.204(3) . ?
O3 C11 1.208(3) . ?
N2 C9 1.369(3) . ?
N2 C6 1.378(3) . ?
N2 Cu1 2.027(2) . ?
C14 C5 1.503(3) . ?
C9 C8 1.439(4) . ?
C9 C10 1.396(4) . ?
C8 C7 1.337(4) . ?
C8 H8 0.94(3) . ?
C5 C6 1.394(3) . ?
C5 C4 1.396(4) . ?
C10 C11 1.505(3) . ?
C10 C1 1.391(4) 2_675 ?
C7 C6 1.448(4) . ?
C7 H7 0.91(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.477(4) . ?
C4 C3 1.441(4) . ?
C2 C3 1.338(4) . ?
C2 C1 1.439(3) . ?
C2 H2 0.91(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 C15 1.475(4) . ?
C3 H3 0.90(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
Cu1 N1 2.011(2) 2_675 ?
Cu1 N2 2.027(2) 2_675 ?
C1 C10 1.391(4) 2_675 ?

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
C11 O4 C12 116.5(2) . . ?
C14 O2 C15 116.9(2) . . ?
C4 N1 Cu1 127.46(16) . . ?
C1 N1 C4 106.0(2) . . ?
C1 N1 Cu1 126.55(16) . . ?
C9 N2 C6 105.5(2) . . ?
C9 N2 Cu1 126.69(17) . . ?
C6 N2 Cu1 127.79(17) . . ?
O2 C14 C5 112.5(2) . . ?
O1 C14 O2 123.8(2) . . ?
O1 C14 C5 123.6(2) . . ?
N2 C9 C8 110.5(2) . . ?
N2 C9 C10 124.8(2) . . ?
C10 C9 C8 124.7(2) . . ?
C9 C8 H8 124.2(18) . . ?
C7 C8 C9 107.1(2) . . ?
C7 C8 H8 128.5(18) . . ?
C6 C5 C14 119.3(2) . . ?
C6 C5 C4 125.2(2) . . ?
C4 C5 C14 115.5(2) . . ?
C9 C10 C11 118.0(2) . . ?
C1 C10 C9 125.9(2) 2_675 . ?
C1 C10 C11 116.1(2) 2_675 . ?
C8 C7 C6 107.1(2) . . ?
C8 C7 H7 127.5(17) . . ?
C6 C7 H7 125.4(17) . . ?
N2 C6 C5 124.5(2) . . ?
N2 C6 C7 109.7(2) . . ?
C5 C6 C7 125.8(2) . . ?
O4 C12 H12A 110.3 . . ?
O4 C12 H12B 110.3 . . ?
O4 C12 C13 107.2(2) . . ?
H12A C12 H12B 108.5 . . ?
C13 C12 H12A 110.3 . . ?
C13 C12 H12B 110.3 . . ?
N1 C4 C5 125.5(2) . . ?
N1 C4 C3 109.4(2) . . ?
C5 C4 C3 125.0(2) . . ?
C3 C2 C1 106.9(2) . . ?
C3 C2 H2 128.2(17) . . ?
C1 C2 H2 124.9(17) . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
C4 C3 H3 122.4(18) . . ?
C2 C3 C4 107.6(2) . . ?
C2 C3 H3 130.0(18) . . ?
O4 C11 C10 110.5(2) . . ?
O3 C11 O4 124.0(2) . . ?
O3 C11 C10 125.4(2) . . ?
O2 C15 C16 109.8(2) . . ?
O2 C15 H15A 109.7 . . ?
O2 C15 H15B 109.7 . . ?
C16 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 Cu1 N1 180.000(1) . 2_675 ?
N1 Cu1 N2 90.52(8) 2_675 . ?
N1 Cu1 N2 89.48(8) . . ?
N1 Cu1 N2 90.52(8) . 2_675 ?
N1 Cu1 N2 89.48(8) 2_675 2_675 ?
N2 Cu1 N2 180.000(1) . 2_675 ?
N1 C1 C10 125.5(2) . 2_675 ?
N1 C1 C2 110.1(2) . . ?
C10 C1 C2 124.4(2) 2_675 . ?

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
O2 C14 C5 C6 51.2(3) . . . . ?
O2 C14 C5 C4 -130.6(2) . . . . ?
N1 C4 C3 C2 1.1(3) . . . . ?
O1 C14 C5 C6 -130.6(3) . . . . ?
O1 C14 C5 C4 47.7(3) . . . . ?
N2 C9 C8 C7 -1.1(3) . . . . ?
N2 C9 C10 C11 176.0(2) . . . . ?
N2 C9 C10 C1 -1.6(4) . . . 2_675 ?
C14 O2 C15 C16 119.5(3) . . . . ?
C14 C5 C6 N2 177.7(2) . . . . ?
C14 C5 C6 C7 -0.7(4) . . . . ?
C14 C5 C4 N1 -178.9(2) . . . . ?
C14 C5 C4 C3 2.6(4) . . . . ?
C9 N2 C6 C5 179.4(2) . . . . ?
C9 N2 C6 C7 -2.0(3) . . . . ?
C9 N2 Cu1 N1 1.5(2) . . . 2_675 ?
C9 N2 Cu1 N1 -178.5(2) . . . . ?
C9 N2 Cu1 N2 -30(100) . . . 2_675 ?
C9 C8 C7 C6 -0.2(3) . . . . ?
C9 C10 C11 O4 -62.2(3) . . . . ?
C9 C10 C11 O3 119.9(3) . . . . ?
C8 C9 C10 C11 -5.5(4) . . . . ?
C8 C9 C10 C1 176.9(2) . . . 2_675 ?
C8 C7 C6 N2 1.4(3) . . . . ?
C8 C7 C6 C5 180.0(2) . . . . ?
C5 C4 C3 C2 179.8(2) . . . . ?
C10 C9 C8 C7 -179.7(3) . . . . ?
C6 N2 C9 C8 1.9(3) . . . . ?
C6 N2 C9 C10 -179.5(2) . . . . ?
C6 N2 Cu1 N1 180.0(2) . . . 2_675 ?
C6 N2 Cu1 N1 0.0(2) . . . . ?
C6 N2 Cu1 N2 149(100) . . . 2_675 ?
C6 C5 C4 N1 -0.8(4) . . . . ?
C6 C5 C4 C3 -179.2(2) . . . . ?
C12 O4 C11 O3 0.8(4) . . . . ?
C12 O4 C11 C10 -177.1(2) . . . . ?
C4 N1 Cu1 N1 172(100) . . . 2_675 ?
C4 N1 Cu1 N2 179.0(2) . . . 2_675 ?
C4 N1 Cu1 N2 -1.0(2) . . . . ?
C4 N1 C1 C10 -177.6(2) . . . 2_675 ?
C4 N1 C1 C2 0.8(3) . . . . ?
C4 C5 C6 N2 -0.4(4) . . . . ?
C4 C5 C6 C7 -178.7(2) . . . . ?
C3 C2 C1 N1 -0.1(3) . . . . ?
C3 C2 C1 C10 178.3(2) . . . 2_675 ?
C11 O4 C12 C13 163.6(2) . . . . ?
C15 O2 C14 O1 3.7(4) . . . . ?
C15 O2 C14 C5 -178.1(2) . . . . ?
Cu1 N1 C4 C5 1.6(4) . . . . ?
Cu1 N1 C4 C3 -179.76(16) . . . . ?
Cu1 N1 C1 C10 1.0(4) . . . 2_675 ?
Cu1 N1 C1 C2 179.43(17) . . . . ?
Cu1 N2 C9 C8 -179.35(16) . . . . ?
Cu1 N2 C9 C10 -0.7(4) . . . . ?
Cu1 N2 C6 C5 0.7(4) . . . . ?
Cu1 N2 C6 C7 179.25(16) . . . . ?
C1 N1 C4 C5 -179.8(2) . . . . ?
C1 N1 C4 C3 -1.2(3) . . . . ?
C1 N1 Cu1 N1 -6(100) . . . 2_675 ?
C1 N1 Cu1 N2 -179.3(2) . . . . ?
C1 N1 Cu1 N2 0.7(2) . . . 2_675 ?
C1 C10 C11 O4 115.5(2) 2_675 . . . ?
C1 C10 C11 O3 -62.3(3) 2_675 . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, Hexane'
