# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_CuNPy3Cl_dsord
_database_code_depnum_ccdc_archive 'CCDC 1055957'
_audit_update_record             
;
2015-03-24 deposited with the CCDC.
2015-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        CuNPy3Cl
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34.08 H27.23 Cl Cu N4 O1.58'
_chemical_formula_weight         616.91

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'
O O 0.0492 0.0322 '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/c'
_space_group_name_Hall           '-P 2ybc'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.05130(10)
_cell_length_b                   28.1929(2)
_cell_length_c                   12.21890(10)
_cell_angle_alpha                90
_cell_angle_beta                 112.2430(10)
_cell_angle_gamma                90
_cell_volume                     3204.88(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.0(2)
_cell_measurement_reflns_used    31217
_cell_measurement_theta_min      4.2100
_cell_measurement_theta_max      76.2520

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             1273
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    1.992
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.818
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
  CrysAlisPro, Agilent Technologies,
  Version 1.171.37.35
  Empirical absorption correction using spherical 
  harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_crystal_treatment        
;
attached with Exxon Paratone N, to a short length 
of fibre supported on a thin piece of copper wire 
inserted in a copper mounting pin.  The crystal was 
quenched in a cold nitrogen gas stream from an 
Oxford Cryosystems Cryostream. 
;



_diffrn_ambient_temperature      150.0(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.5861
_diffrn_measurement_method       ω
_diffrn_reflns_number            62752
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.135
_diffrn_reflns_theta_max         76.593
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6714
_reflns_number_gt                6371
_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.
 
 _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       
;
  CrysAlisPro, Agilent Technologies,
;
_computing_cell_refinement       
;
  CrysAlisPro, Agilent Technologies,
;
_computing_data_reduction        
;
  CrysAlisPro, Agilent Technologies,
;

_computing_structure_solution    'SIR97 (Altomare, et. al. 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
  ORTEP3 for Windows (Farrugia, L., 1997)
  ORTEPII  (Johnson,C.K., 1976). 
  shelXle (Hbschle, C. B., et. al. 2011)
  WinGX (Farrugia, L., 1999)
;
_computing_publication_material  ?

_refine_special_details          
;         
The structure includes channels containing disordered and only 
partially resolved methanol solvate. Residual density was assigned 
as four partially occupied methanol oxygen and carbon sites with 
occupancies totalling 1.075. A further site was assigned as 0.5 occupancy 
water oxygen atom. No hydrogens were included in the model for the 
methanol and water oxygen sites.

The remaining electron density could not be satisfactorily assigned. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²+5.0P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6714
_refine_ls_number_parameters     388
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.1032
_refine_ls_wR_factor_ref         0.3310
_refine_ls_wR_factor_gt          0.3279
_refine_ls_goodness_of_fit_ref   1.293
_refine_ls_restrained_S_all      1.296
_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 1.42891(7) 0.48848(2) 0.56756(6) 0.0355(3) Uani 1 1 d . . . . .
Cl1 Cl 1.33802(13) 0.53898(4) 0.38877(11) 0.0435(4) Uani 1 1 d . . . . .
N1 N 1.2861(4) 0.43487(12) 0.5147(3) 0.0291(7) Uani 1 1 d . . . . .
N2 N 0.5788(4) 0.03091(14) 0.8025(3) 0.0355(8) Uani 1 1 d . . . . .
N3 N 0.1866(5) 0.18546(18) -0.4663(3) 0.0439(10) Uani 1 1 d . . . . .
N4 N 0.6680(4) 0.21271(12) 0.2775(3) 0.0278(7) Uani 1 1 d . . . . .
C1 C 1.2529(5) 0.40867(15) 0.5911(4) 0.0308(8) Uani 1 1 d . . . . .
H1 H 1.2995 0.4155 0.6730 0.037 Uiso 1 1 calc R U . . .
C2 C 1.1537(5) 0.37172(15) 0.5580(4) 0.0299(8) Uani 1 1 d . . . . .
H2 H 1.1341 0.3539 0.6161 0.036 Uiso 1 1 calc R U . . .
C3 C 1.0837(4) 0.36134(14) 0.4384(3) 0.0259(8) Uani 1 1 d . . . . .
C4 C 1.1194(5) 0.38856(15) 0.3584(4) 0.0305(8) Uani 1 1 d . . . . .
H4 H 1.0749 0.3824 0.2760 0.037 Uiso 1 1 calc R U . . .
C5 C 1.2198(5) 0.42469(15) 0.3991(4) 0.0318(9) Uani 1 1 d . . . . .
H5 H 1.2427 0.4429 0.3432 0.038 Uiso 1 1 calc R U . . .
C6 C 0.9751(4) 0.32294(13) 0.3978(3) 0.0237(7) Uani 1 1 d . . . . .
C7 C 0.8830(4) 0.31242(14) 0.4565(3) 0.0266(8) Uani 1 1 d . . . . .
H7 H 0.8905 0.3301 0.5248 0.032 Uiso 1 1 calc R U . . .
C8 C 0.7816(4) 0.27686(14) 0.4170(3) 0.0258(8) Uani 1 1 d . . . . .
H8 H 0.7192 0.2707 0.4574 0.031 Uiso 1 1 calc R U . . .
C9 C 0.7702(4) 0.24988(13) 0.3177(3) 0.0249(7) Uani 1 1 d . . . . .
C10 C 0.8614(5) 0.26024(14) 0.2583(4) 0.0291(8) Uani 1 1 d . . . . .
H10 H 0.8548 0.2423 0.1906 0.035 Uiso 1 1 calc R U . . .
C11 C 0.9608(4) 0.29630(14) 0.2974(4) 0.0283(8) Uani 1 1 d . . . . .
H11 H 1.0209 0.3032 0.2553 0.034 Uiso 1 1 calc R U . . .
C12 C 0.4995(5) 0.02248(16) 0.6883(4) 0.0369(10) Uani 1 1 d . . . . .
H12 H 0.4341 -0.0034 0.6695 0.044 Uiso 1 1 calc R U . . .
C13 C 0.5076(5) 0.04961(15) 0.5956(4) 0.0342(9) Uani 1 1 d . . . . .
H13 H 0.4478 0.0425 0.5161 0.041 Uiso 1 1 calc R U . . .
C14 C 0.6038(5) 0.08703(15) 0.6206(4) 0.0313(8) Uani 1 1 d . . . . .
C15 C 0.6861(5) 0.09597(17) 0.7390(4) 0.0391(10) Uani 1 1 d . . . . .
H15 H 0.7525 0.1216 0.7598 0.047 Uiso 1 1 calc R U . . .
C16 C 0.6719(5) 0.06769(18) 0.8268(4) 0.0389(10) Uani 1 1 d . . . . .
H16 H 0.7297 0.0744 0.9070 0.047 Uiso 1 1 calc R U . . .
C17 C 0.6210(5) 0.11715(14) 0.5269(4) 0.0292(8) Uani 1 1 d . . . . .
C18 C 0.5054(5) 0.12614(14) 0.4197(4) 0.0308(8) Uani 1 1 d . . . . .
H18 H 0.4157 0.1108 0.4034 0.037 Uiso 1 1 calc R U . . .
C19 C 0.5214(5) 0.15725(14) 0.3376(3) 0.0287(8) Uani 1 1 d . . . . .
H19 H 0.4419 0.1635 0.2661 0.034 Uiso 1 1 calc R U . . .
C20 C 0.6526(4) 0.17952(13) 0.3584(3) 0.0262(8) Uani 1 1 d . . . . .
C21 C 0.7695(4) 0.16903(15) 0.4626(4) 0.0300(8) Uani 1 1 d . . . . .
H21 H 0.8608 0.1828 0.4765 0.036 Uiso 1 1 calc R U . . .
C22 C 0.7527(5) 0.13868(15) 0.5454(4) 0.0321(9) Uani 1 1 d . . . . .
H22 H 0.8326 0.1324 0.6165 0.038 Uiso 1 1 calc R U . . .
C23 C 0.1813(5) 0.2251(2) -0.4074(4) 0.0434(11) Uani 1 1 d . . . . .
H23 H 0.1233 0.2506 -0.4505 0.052 Uiso 1 1 calc R U . . .
C24 C 0.2564(5) 0.23089(17) -0.2864(4) 0.0335(9) Uani 1 1 d . . . . .
H24 H 0.2480 0.2597 -0.2491 0.040 Uiso 1 1 calc R U . . .
C25 C 0.3438(4) 0.19466(15) -0.2198(3) 0.0281(8) Uani 1 1 d . . . . .
C26 C 0.3496(5) 0.15359(17) -0.2820(4) 0.0363(9) Uani 1 1 d . . . . .
H26 H 0.4077 0.1276 -0.2417 0.044 Uiso 1 1 calc R U . . .
C27 C 0.2701(6) 0.1509(2) -0.4027(4) 0.0429(11) Uani 1 1 d . . . . .
H27 H 0.2759 0.1224 -0.4424 0.052 Uiso 1 1 calc R U . . .
C28 C 0.4269(4) 0.19902(14) -0.0902(3) 0.0263(8) Uani 1 1 d . . . . .
C29 C 0.4419(4) 0.24291(14) -0.0335(4) 0.0278(8) Uani 1 1 d . . . . .
H29 H 0.3963 0.2701 -0.0779 0.033 Uiso 1 1 calc R U . . .
C30 C 0.5221(4) 0.24744(14) 0.0865(4) 0.0281(8) Uani 1 1 d . . . . .
H30 H 0.5331 0.2778 0.1228 0.034 Uiso 1 1 calc R U . . .
C31 C 0.5868(4) 0.20801(13) 0.1543(3) 0.0247(7) Uani 1 1 d . . . . .
C32 C 0.5712(4) 0.16390(13) 0.0995(3) 0.0274(8) Uani 1 1 d . . . . .
H32 H 0.6144 0.1366 0.1447 0.033 Uiso 1 1 calc R U . . .
C33 C 0.4927(4) 0.15973(13) -0.0210(3) 0.0263(8) Uani 1 1 d . . . . .
H33 H 0.4834 0.1295 -0.0574 0.032 Uiso 1 1 calc R U . . .
O1M O 0.983(3) 0.4769(10) 0.628(2) 0.073(6) Uiso 0.2 1 d D . P A -1
C1M C 1.002(3) 0.4977(11) 0.530(2) 0.046(6) Uiso 0.2 1 d D . P A -1
H1M1 H 1.0089 0.5323 0.5401 0.069 Uiso 0.2 1 calc R U P A -1
H1M2 H 0.9207 0.4898 0.4577 0.069 Uiso 0.2 1 calc R U P A -1
H1M3 H 1.0913 0.4857 0.5248 0.069 Uiso 0.2 1 calc R U P A -1
O4M O 1.008(3) 0.4960(11) -0.012(2) 0.031(5) Uiso 0.125 1 d D . P B -1
C4M C 1.087(5) 0.4665(17) 0.083(4) 0.059(11) Uiso 0.125 1 d D . P B -1
H4M1 H 1.1769 0.4573 0.0760 0.089 Uiso 0.125 1 calc R U P B -1
H4M2 H 1.0302 0.4380 0.0822 0.089 Uiso 0.125 1 calc R U P B -1
H4M3 H 1.1075 0.4835 0.1577 0.089 Uiso 0.125 1 calc R U P B -1
O2M O 1.1805(10) 0.4446(3) 0.8412(9) 0.0209(18) Uiso 0.25 1 d D . P . .
C2M C 1.117(3) 0.4837(8) 0.775(3) 0.064(6) Uiso 0.25 1 d D . P . .
H2M1 H 1.0215 0.4884 0.7781 0.095 Uiso 0.25 1 calc R U P . .
H2M2 H 1.1067 0.4788 0.6931 0.095 Uiso 0.25 1 calc R U P . .
H2M3 H 1.1763 0.5117 0.8073 0.095 Uiso 0.25 1 calc R U P . .
O3M O 0.9604(11) 0.3679(4) 0.7729(10) 0.069(2) Uiso 0.5 1 d D . P . .
C3M C 1.0962(8) 0.3401(3) 0.7941(7) 0.0290(15) Uiso 0.5 1 d D . P . .
H3M1 H 1.1698 0.3612 0.7869 0.044 Uiso 0.5 1 calc R U P . .
H3M2 H 1.0762 0.3146 0.7355 0.044 Uiso 0.5 1 calc R U P . .
H3M3 H 1.1307 0.3263 0.8737 0.044 Uiso 0.5 1 calc R U P . .
O1W O 0.9388(6) 0.4486(2) 0.7352(5) 0.0318(12) Uiso 0.5 1 d . . P . .


_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 2.012(4) 2_756 ?
Cu1 N1 2.015(3) . ?
Cu1 Cl1 2.3294(15) 3_866 ?
Cu1 Cl1 2.4744(14) . ?
Cu1 Cu1 2.6411(13) 3_866 ?
Cl1 Cu1 2.3295(14) 3_866 ?
N1 C1 1.329(5) . ?
N1 C5 1.345(5) . ?
N2 C12 1.340(6) . ?
N2 C16 1.353(6) . ?
N2 Cu1 2.012(4) 2_746 ?
N3 C27 1.329(7) . ?
N3 C23 1.342(8) . ?
N4 C20 1.412(5) . ?
N4 C9 1.419(5) . ?
N4 C31 1.421(5) . ?
C1 C2 1.392(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.392(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(5) . ?
C3 C6 1.483(5) . ?
C4 C5 1.387(6) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C11 1.398(5) . ?
C6 C7 1.401(5) . ?
C7 C8 1.380(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.400(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.399(6) . ?
C10 C11 1.378(6) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.395(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.391(6) . ?
C14 C17 1.486(5) . ?
C15 C16 1.387(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.395(6) . ?
C17 C18 1.406(6) . ?
C18 C19 1.388(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.394(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.399(6) . ?
C21 C22 1.384(6) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.391(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.391(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.398(6) . ?
C25 C28 1.490(5) . ?
C26 C27 1.388(6) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.398(6) . ?
C28 C33 1.398(5) . ?
C29 C30 1.386(6) . ?
C29 H29 0.9500 . ?
C30 C31 1.392(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.393(5) . ?
C32 C33 1.388(5) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
O1M C1M 1.404(18) . ?
O1M O1W 1.74(2) . ?
C1M H1M1 0.9800 . ?
C1M H1M2 0.9800 . ?
C1M H1M3 0.9800 . ?
O4M C4M 1.40(2) . ?
C4M H4M1 0.9800 . ?
C4M H4M2 0.9800 . ?
C4M H4M3 0.9800 . ?
O2M C2M 1.372(17) . ?
C2M H2M1 0.9800 . ?
C2M H2M2 0.9800 . ?
C2M H2M3 0.9800 . ?
O3M C3M 1.508(11) . ?
C3M H3M1 0.9800 . ?
C3M H3M2 0.9800 . ?
C3M H3M3 0.9800 . ?

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 N1 117.62(16) 2_756 . ?
N2 Cu1 Cl1 110.64(13) 2_756 3_866 ?
N1 Cu1 Cl1 110.89(11) . 3_866 ?
N2 Cu1 Cl1 104.05(12) 2_756 . ?
N1 Cu1 Cl1 99.69(11) . . ?
Cl1 Cu1 Cl1 113.37(4) 3_866 . ?
N2 Cu1 Cu1 122.57(13) 2_756 3_866 ?
N1 Cu1 Cu1 118.18(11) . 3_866 ?
Cl1 Cu1 Cu1 59.31(4) 3_866 3_866 ?
Cl1 Cu1 Cu1 54.06(4) . 3_866 ?
Cu1 Cl1 Cu1 66.63(4) 3_866 . ?
C1 N1 C5 117.6(3) . . ?
C1 N1 Cu1 122.0(3) . . ?
C5 N1 Cu1 120.4(3) . . ?
C12 N2 C16 117.0(4) . . ?
C12 N2 Cu1 122.0(3) . 2_746 ?
C16 N2 Cu1 120.8(3) . 2_746 ?
C27 N3 C23 116.2(4) . . ?
C20 N4 C9 120.3(3) . . ?
C20 N4 C31 120.6(3) . . ?
C9 N4 C31 119.1(3) . . ?
N1 C1 C2 123.7(4) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C3 C2 C1 119.0(4) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 117.3(4) . . ?
C4 C3 C6 121.3(3) . . ?
C2 C3 C6 121.3(3) . . ?
C5 C4 C3 119.9(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
N1 C5 C4 122.5(4) . . ?
N1 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C11 C6 C7 117.8(3) . . ?
C11 C6 C3 120.3(3) . . ?
C7 C6 C3 121.9(3) . . ?
C8 C7 C6 121.2(4) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 120.3(4) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 118.8(3) . . ?
C10 C9 N4 120.4(3) . . ?
C8 C9 N4 120.8(3) . . ?
C11 C10 C9 120.3(4) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C6 121.4(4) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
N2 C12 C13 123.6(4) . . ?
N2 C12 H12 118.2 . . ?
C13 C12 H12 118.2 . . ?
C14 C13 C12 119.3(4) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 117.3(4) . . ?
C13 C14 C17 122.7(4) . . ?
C15 C14 C17 120.0(4) . . ?
C16 C15 C14 120.4(4) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
N2 C16 C15 122.4(4) . . ?
N2 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
C22 C17 C18 118.1(4) . . ?
C22 C17 C14 120.2(4) . . ?
C18 C17 C14 121.6(4) . . ?
C19 C18 C17 120.4(4) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 120.9(4) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C21 118.8(3) . . ?
C19 C20 N4 121.2(4) . . ?
C21 C20 N4 120.0(4) . . ?
C22 C21 C20 120.2(4) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C17 121.4(4) . . ?
C21 C22 H22 119.3 . . ?
C17 C22 H22 119.3 . . ?
N3 C23 C24 123.5(4) . . ?
N3 C23 H23 118.3 . . ?
C24 C23 H23 118.3 . . ?
C23 C24 C25 120.3(4) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C26 115.9(4) . . ?
C24 C25 C28 122.5(4) . . ?
C26 C25 C28 121.6(4) . . ?
C27 C26 C25 119.8(4) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
N3 C27 C26 124.3(5) . . ?
N3 C27 H27 117.9 . . ?
C26 C27 H27 117.9 . . ?
C29 C28 C33 117.6(3) . . ?
C29 C28 C25 120.8(4) . . ?
C33 C28 C25 121.6(4) . . ?
C30 C29 C28 121.1(4) . . ?
C30 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
C29 C30 C31 120.7(4) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C30 C31 C32 119.0(3) . . ?
C30 C31 N4 120.5(3) . . ?
C32 C31 N4 120.5(3) . . ?
C33 C32 C31 120.1(4) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C33 C28 121.5(4) . . ?
C32 C33 H33 119.2 . . ?
C28 C33 H33 119.2 . . ?
C1M O1M O1W 173(2) . . ?
O1M C1M H1M1 109.5 . . ?
O1M C1M H1M2 109.5 . . ?
H1M1 C1M H1M2 109.5 . . ?
O1M C1M H1M3 109.5 . . ?
H1M1 C1M H1M3 109.5 . . ?
H1M2 C1M H1M3 109.5 . . ?
O4M C4M H4M1 109.5 . . ?
O4M C4M H4M2 109.5 . . ?
H4M1 C4M H4M2 109.5 . . ?
O4M C4M H4M3 109.5 . . ?
H4M1 C4M H4M3 109.5 . . ?
H4M2 C4M H4M3 109.5 . . ?
O2M C2M H2M1 109.5 . . ?
O2M C2M H2M2 109.5 . . ?
H2M1 C2M H2M2 109.5 . . ?
O2M C2M H2M3 109.5 . . ?
H2M1 C2M H2M3 109.5 . . ?
H2M2 C2M H2M3 109.5 . . ?
O3M C3M H3M1 109.5 . . ?
O3M C3M H3M2 109.5 . . ?
H3M1 C3M H3M2 109.5 . . ?
O3M C3M H3M3 109.5 . . ?
H3M1 C3M H3M3 109.5 . . ?
H3M2 C3M H3M3 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
C5 N1 C1 C2 -0.2(7) . . . . ?
Cu1 N1 C1 C2 179.2(3) . . . . ?
N1 C1 C2 C3 -0.4(7) . . . . ?
C1 C2 C3 C4 0.9(6) . . . . ?
C1 C2 C3 C6 -178.9(4) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C6 C3 C4 C5 179.1(4) . . . . ?
C1 N1 C5 C4 0.4(7) . . . . ?
Cu1 N1 C5 C4 -179.1(3) . . . . ?
C3 C4 C5 N1 0.1(7) . . . . ?
C4 C3 C6 C11 33.7(6) . . . . ?
C2 C3 C6 C11 -146.4(4) . . . . ?
C4 C3 C6 C7 -145.4(4) . . . . ?
C2 C3 C6 C7 34.4(6) . . . . ?
C11 C6 C7 C8 0.2(6) . . . . ?
C3 C6 C7 C8 179.4(4) . . . . ?
C6 C7 C8 C9 1.0(6) . . . . ?
C7 C8 C9 C10 -1.2(6) . . . . ?
C7 C8 C9 N4 178.9(4) . . . . ?
C20 N4 C9 C10 133.6(4) . . . . ?
C31 N4 C9 C10 -43.3(5) . . . . ?
C20 N4 C9 C8 -46.5(6) . . . . ?
C31 N4 C9 C8 136.6(4) . . . . ?
C8 C9 C10 C11 0.2(6) . . . . ?
N4 C9 C10 C11 -179.9(4) . . . . ?
C9 C10 C11 C6 1.0(6) . . . . ?
C7 C6 C11 C10 -1.2(6) . . . . ?
C3 C6 C11 C10 179.6(4) . . . . ?
C16 N2 C12 C13 -0.6(7) . . . . ?
Cu1 N2 C12 C13 -176.5(4) 2_746 . . . ?
N2 C12 C13 C14 1.1(8) . . . . ?
C12 C13 C14 C15 -1.1(7) . . . . ?
C12 C13 C14 C17 178.9(4) . . . . ?
C13 C14 C15 C16 0.8(7) . . . . ?
C17 C14 C15 C16 -179.3(5) . . . . ?
C12 N2 C16 C15 0.2(7) . . . . ?
Cu1 N2 C16 C15 176.1(4) 2_746 . . . ?
C14 C15 C16 N2 -0.3(8) . . . . ?
C13 C14 C17 C22 -151.0(5) . . . . ?
C15 C14 C17 C22 29.1(7) . . . . ?
C13 C14 C17 C18 31.2(7) . . . . ?
C15 C14 C17 C18 -148.7(5) . . . . ?
C22 C17 C18 C19 -2.8(6) . . . . ?
C14 C17 C18 C19 175.1(4) . . . . ?
C17 C18 C19 C20 1.2(6) . . . . ?
C18 C19 C20 C21 1.7(6) . . . . ?
C18 C19 C20 N4 -177.3(4) . . . . ?
C9 N4 C20 C19 150.9(4) . . . . ?
C31 N4 C20 C19 -32.2(6) . . . . ?
C9 N4 C20 C21 -28.1(6) . . . . ?
C31 N4 C20 C21 148.8(4) . . . . ?
C19 C20 C21 C22 -2.8(6) . . . . ?
N4 C20 C21 C22 176.1(4) . . . . ?
C20 C21 C22 C17 1.2(7) . . . . ?
C18 C17 C22 C21 1.6(7) . . . . ?
C14 C17 C22 C21 -176.3(4) . . . . ?
C27 N3 C23 C24 -0.6(7) . . . . ?
N3 C23 C24 C25 0.5(7) . . . . ?
C23 C24 C25 C26 -0.1(6) . . . . ?
C23 C24 C25 C28 179.8(4) . . . . ?
C24 C25 C26 C27 -0.4(6) . . . . ?
C28 C25 C26 C27 179.8(4) . . . . ?
C23 N3 C27 C26 0.1(8) . . . . ?
C25 C26 C27 N3 0.4(8) . . . . ?
C24 C25 C28 C29 -12.0(6) . . . . ?
C26 C25 C28 C29 167.8(4) . . . . ?
C24 C25 C28 C33 168.1(4) . . . . ?
C26 C25 C28 C33 -12.1(6) . . . . ?
C33 C28 C29 C30 1.6(6) . . . . ?
C25 C28 C29 C30 -178.3(3) . . . . ?
C28 C29 C30 C31 -1.8(6) . . . . ?
C29 C30 C31 C32 0.8(6) . . . . ?
C29 C30 C31 N4 -179.5(4) . . . . ?
C20 N4 C31 C30 136.5(4) . . . . ?
C9 N4 C31 C30 -46.6(5) . . . . ?
C20 N4 C31 C32 -43.8(6) . . . . ?
C9 N4 C31 C32 133.1(4) . . . . ?
C30 C31 C32 C33 0.3(6) . . . . ?
N4 C31 C32 C33 -179.5(4) . . . . ?
C31 C32 C33 C28 -0.4(6) . . . . ?
C29 C28 C33 C32 -0.5(6) . . . . ?
C25 C28 C33 C32 179.4(4) . . . . ?

_refine_diff_density_max         3.595
_refine_diff_density_min         -0.844
_refine_diff_density_rms         0.183

####################################################################### 
# 
# 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_CuNPy3Cl_sq
_database_code_depnum_ccdc_archive 'CCDC 1055958'
_audit_update_record             
;
2015-03-24 deposited with the CCDC.
2015-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        CuNPy3Cl
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_sum            'C33 H24 Cl Cu N4'
_chemical_formula_moiety         '(C33 H24 Br1 Cu1 N4)n'
_chemical_formula_weight         575.55

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14




_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.05130(10)
_cell_length_b                   28.1929(2)
_cell_length_c                   12.21890(10)
_cell_angle_alpha                90
_cell_angle_beta                 112.2430(10)
_cell_angle_gamma                90
_cell_volume                     3204.88(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.0(2)
_cell_measurement_reflns_used    31217
_cell_measurement_theta_min      4.2100
_cell_measurement_theta_max      76.2520

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    1.992
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.818
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
  CrysAlisPro, Agilent Technologies,
  Version 1.171.37.35
  Empirical absorption correction using spherical 
  harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_crystal_treatment        
;
attached with Exxon Paratone N, to a short length 
of fibre supported on a thin piece of copper wire 
inserted in a copper mounting pin.  The crystal was 
quenched in a cold nitrogen gas stream from an 
Oxford Cryosystems Cryostream. 
;


_diffrn_ambient_temperature      150.0(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.5861
_diffrn_measurement_method       ω
_diffrn_reflns_number            62752
_diffrn_reflns_av_unetI/netI     0.0113
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.135
_diffrn_reflns_theta_max         76.593
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6714
_reflns_number_gt                6371
_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       
;
  CrysAlisPro, Agilent Technologies,
;
_computing_cell_refinement       
;
  CrysAlisPro, Agilent Technologies,
;
_computing_data_reduction        
;
  CrysAlisPro, Agilent Technologies,
;

_computing_structure_solution    'SIR97 (Altomare, et. al. 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
  ORTEP3 for Windows (Farrugia, L., 1997)
  ORTEPII  (Johnson,C.K., 1976). 
  shelXle (Hbschle, C. B., et. al. 2011)
  WinGX (Farrugia, L., 1999)
;
_computing_publication_material  ?

_refine_special_details          SQUEEZE


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.10P)²+5.0P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6714
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1787
_refine_ls_wR_factor_gt          0.1771
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 1.42905(5) 0.48846(2) 0.56771(4) 0.03640(16) Uani 1 1 d . . . . .
Cl1 Cl 1.33799(9) 0.53896(3) 0.38859(7) 0.0452(2) Uani 1 1 d . . . . .
N1 N 1.2865(2) 0.43487(8) 0.5152(2) 0.0301(5) Uani 1 1 d . . . . .
N2 N 0.5795(3) 0.03093(9) 0.8026(2) 0.0353(5) Uani 1 1 d . . . . .
N3 N 0.1868(3) 0.18586(11) -0.4661(2) 0.0441(6) Uani 1 1 d . . . . .
N4 N 0.6678(3) 0.21272(8) 0.27744(18) 0.0285(5) Uani 1 1 d . . . . .
C1 C 1.2528(3) 0.40848(10) 0.5914(2) 0.0315(5) Uani 1 1 d . . . . .
H1 H 1.2995 0.4152 0.6733 0.038 Uiso 1 1 calc R U . . .
C2 C 1.1536(3) 0.37181(10) 0.5580(2) 0.0312(5) Uani 1 1 d . . . . .
H2 H 1.1337 0.3540 0.6161 0.037 Uiso 1 1 calc R U . . .
C3 C 1.0836(3) 0.36136(9) 0.4386(2) 0.0265(5) Uani 1 1 d . . . . .
C4 C 1.1193(3) 0.38850(10) 0.3584(2) 0.0312(5) Uani 1 1 d . . . . .
H4 H 1.0751 0.3823 0.2760 0.037 Uiso 1 1 calc R U . . .
C5 C 1.2193(3) 0.42452(10) 0.3994(2) 0.0320(6) Uani 1 1 d . . . . .
H5 H 1.2418 0.4428 0.3434 0.038 Uiso 1 1 calc R U . . .
C6 C 0.9756(3) 0.32292(9) 0.3980(2) 0.0252(5) Uani 1 1 d . . . . .
C7 C 0.8836(3) 0.31231(9) 0.4567(2) 0.0268(5) Uani 1 1 d . . . . .
H7 H 0.8913 0.3299 0.5252 0.032 Uiso 1 1 calc R U . . .
C8 C 0.7818(3) 0.27679(9) 0.4168(2) 0.0261(5) Uani 1 1 d . . . . .
H8 H 0.7194 0.2706 0.4573 0.031 Uiso 1 1 calc R U . . .
C9 C 0.7700(3) 0.24997(8) 0.3174(2) 0.0255(5) Uani 1 1 d . . . . .
C10 C 0.8610(3) 0.26013(9) 0.2584(2) 0.0294(5) Uani 1 1 d . . . . .
H10 H 0.8545 0.2421 0.1909 0.035 Uiso 1 1 calc R U . . .
C11 C 0.9609(3) 0.29636(9) 0.2975(2) 0.0284(5) Uani 1 1 d . . . . .
H11 H 1.0207 0.3033 0.2552 0.034 Uiso 1 1 calc R U . . .
C12 C 0.4988(4) 0.02266(11) 0.6882(3) 0.0383(6) Uani 1 1 d . . . . .
H12 H 0.4325 -0.0030 0.6695 0.046 Uiso 1 1 calc R U . . .
C13 C 0.5072(3) 0.04963(10) 0.5959(3) 0.0350(6) Uani 1 1 d . . . . .
H13 H 0.4469 0.0426 0.5165 0.042 Uiso 1 1 calc R U . . .
C14 C 0.6043(3) 0.08706(10) 0.6202(2) 0.0316(6) Uani 1 1 d . . . . .
C15 C 0.6863(3) 0.09571(11) 0.7392(3) 0.0386(6) Uani 1 1 d . . . . .
H15 H 0.7530 0.1212 0.7606 0.046 Uiso 1 1 calc R U . . .
C16 C 0.6712(4) 0.06744(12) 0.8258(3) 0.0401(7) Uani 1 1 d . . . . .
H16 H 0.7287 0.0742 0.9061 0.048 Uiso 1 1 calc R U . . .
C17 C 0.6204(3) 0.11721(9) 0.5267(2) 0.0296(5) Uani 1 1 d . . . . .
C18 C 0.5061(3) 0.12615(9) 0.4197(2) 0.0309(5) Uani 1 1 d . . . . .
H18 H 0.4165 0.1107 0.4031 0.037 Uiso 1 1 calc R U . . .
C19 C 0.5220(3) 0.15726(9) 0.3378(2) 0.0293(5) Uani 1 1 d . . . . .
H19 H 0.4424 0.1634 0.2665 0.035 Uiso 1 1 calc R U . . .
C20 C 0.6527(3) 0.17965(9) 0.3580(2) 0.0268(5) Uani 1 1 d . . . . .
C21 C 0.7700(3) 0.16892(10) 0.4626(2) 0.0308(5) Uani 1 1 d . . . . .
H21 H 0.8615 0.1825 0.4767 0.037 Uiso 1 1 calc R U . . .
C22 C 0.7525(3) 0.13858(10) 0.5449(2) 0.0327(6) Uani 1 1 d . . . . .
H22 H 0.8324 0.1321 0.6157 0.039 Uiso 1 1 calc R U . . .
C23 C 0.1818(3) 0.22507(13) -0.4072(3) 0.0436(7) Uani 1 1 d . . . . .
H23 H 0.1237 0.2506 -0.4504 0.052 Uiso 1 1 calc R U . . .
C24 C 0.2563(3) 0.23103(11) -0.2864(3) 0.0349(6) Uani 1 1 d . . . . .
H24 H 0.2474 0.2598 -0.2493 0.042 Uiso 1 1 calc R U . . .
C25 C 0.3441(3) 0.19474(10) -0.2195(2) 0.0285(5) Uani 1 1 d . . . . .
C26 C 0.3497(3) 0.15375(11) -0.2825(3) 0.0369(6) Uani 1 1 d . . . . .
H26 H 0.4084 0.1278 -0.2427 0.044 Uiso 1 1 calc R U . . .
C27 C 0.2702(4) 0.15108(13) -0.4023(3) 0.0437(7) Uani 1 1 d . . . . .
H27 H 0.2752 0.1226 -0.4420 0.052 Uiso 1 1 calc R U . . .
C28 C 0.4265(3) 0.19896(9) -0.0901(2) 0.0264(5) Uani 1 1 d . . . . .
C29 C 0.4420(3) 0.24293(9) -0.0332(2) 0.0282(5) Uani 1 1 d . . . . .
H29 H 0.3966 0.2701 -0.0777 0.034 Uiso 1 1 calc R U . . .
C30 C 0.5223(3) 0.24752(9) 0.0867(2) 0.0285(5) Uani 1 1 d . . . . .
H30 H 0.5333 0.2778 0.1232 0.034 Uiso 1 1 calc R U . . .
C31 C 0.5869(3) 0.20789(9) 0.1540(2) 0.0255(5) Uani 1 1 d . . . . .
C32 C 0.5711(3) 0.16387(9) 0.0989(2) 0.0280(5) Uani 1 1 d . . . . .
H32 H 0.6144 0.1366 0.1439 0.034 Uiso 1 1 calc R U . . .
C33 C 0.4925(3) 0.15970(9) -0.0213(2) 0.0277(5) Uani 1 1 d . . . . .
H33 H 0.4833 0.1295 -0.0578 0.033 Uiso 1 1 calc R 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 N1 2.013(2) . ?
Cu1 N2 2.014(2) 2_756 ?
Cu1 Cl1 2.3279(10) 3_866 ?
Cu1 Cl1 2.4777(9) . ?
Cu1 Cu1 2.6426(9) 3_866 ?
Cl1 Cu1 2.3278(10) 3_866 ?
N1 C1 1.331(4) . ?
N1 C5 1.349(3) . ?
N2 C16 1.338(4) . ?
N2 C12 1.345(4) . ?
N2 Cu1 2.014(2) 2_746 ?
N3 C23 1.330(5) . ?
N3 C27 1.333(5) . ?
N4 C20 1.405(3) . ?
N4 C9 1.420(3) . ?
N4 C31 1.424(3) . ?
C1 C2 1.386(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.391(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(4) . ?
C3 C6 1.480(3) . ?
C4 C5 1.383(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C11 1.397(4) . ?
C6 C7 1.400(4) . ?
C7 C8 1.382(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.398(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(4) . ?
C10 C11 1.385(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.389(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.394(4) . ?
C14 C17 1.481(4) . ?
C15 C16 1.379(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.397(4) . ?
C17 C18 1.398(4) . ?
C18 C19 1.385(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.392(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.405(4) . ?
C21 C22 1.381(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.390(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.396(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.402(4) . ?
C25 C28 1.486(3) . ?
C26 C27 1.378(4) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C33 1.396(4) . ?
C28 C29 1.401(4) . ?
C29 C30 1.386(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.393(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.392(4) . ?
C32 C33 1.384(4) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N2 117.37(10) . 2_756 ?
N1 Cu1 Cl1 110.91(7) . 3_866 ?
N2 Cu1 Cl1 110.85(8) 2_756 3_866 ?
N1 Cu1 Cl1 99.74(7) . . ?
N2 Cu1 Cl1 103.99(8) 2_756 . ?
Cl1 Cu1 Cl1 113.37(3) 3_866 . ?
N1 Cu1 Cu1 118.24(7) . 3_866 ?
N2 Cu1 Cu1 122.70(8) 2_756 3_866 ?
Cl1 Cu1 Cu1 59.40(3) 3_866 3_866 ?
Cl1 Cu1 Cu1 53.97(3) . 3_866 ?
Cu1 Cl1 Cu1 66.63(3) 3_866 . ?
C1 N1 C5 117.0(2) . . ?
C1 N1 Cu1 122.35(18) . . ?
C5 N1 Cu1 120.67(18) . . ?
C16 N2 C12 116.7(2) . . ?
C16 N2 Cu1 121.4(2) . 2_746 ?
C12 N2 Cu1 121.7(2) . 2_746 ?
C23 N3 C27 116.1(3) . . ?
C20 N4 C9 120.4(2) . . ?
C20 N4 C31 120.6(2) . . ?
C9 N4 C31 118.9(2) . . ?
N1 C1 C2 123.8(2) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 119.3(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 117.3(2) . . ?
C2 C3 C6 121.5(2) . . ?
C4 C3 C6 121.2(2) . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 123.1(2) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C11 C6 C7 117.7(2) . . ?
C11 C6 C3 120.5(2) . . ?
C7 C6 C3 121.8(2) . . ?
C8 C7 C6 121.3(2) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 120.4(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 118.9(2) . . ?
C10 C9 N4 120.4(2) . . ?
C8 C9 N4 120.7(2) . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C6 121.3(2) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
N2 C12 C13 123.4(3) . . ?
N2 C12 H12 118.3 . . ?
C13 C12 H12 118.3 . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 116.5(2) . . ?
C13 C14 C17 122.9(2) . . ?
C15 C14 C17 120.6(2) . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
N2 C16 C15 123.3(3) . . ?
N2 C16 H16 118.4 . . ?
C15 C16 H16 118.4 . . ?
C22 C17 C18 117.8(2) . . ?
C22 C17 C14 120.0(2) . . ?
C18 C17 C14 122.3(2) . . ?
C19 C18 C17 120.7(2) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 121.2(2) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C21 118.3(2) . . ?
C19 C20 N4 121.4(2) . . ?
C21 C20 N4 120.3(2) . . ?
C22 C21 C20 120.0(2) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C17 121.8(3) . . ?
C21 C22 H22 119.1 . . ?
C17 C22 H22 119.1 . . ?
N3 C23 C24 124.0(3) . . ?
N3 C23 H23 118.0 . . ?
C24 C23 H23 118.0 . . ?
C23 C24 C25 120.0(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C26 115.5(2) . . ?
C24 C25 C28 122.6(3) . . ?
C26 C25 C28 121.9(2) . . ?
C27 C26 C25 120.0(3) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
N3 C27 C26 124.3(3) . . ?
N3 C27 H27 117.8 . . ?
C26 C27 H27 117.8 . . ?
C33 C28 C29 117.7(2) . . ?
C33 C28 C25 121.6(2) . . ?
C29 C28 C25 120.7(2) . . ?
C30 C29 C28 121.2(2) . . ?
C30 C29 H29 119.4 . . ?
C28 C29 H29 119.4 . . ?
C29 C30 C31 120.2(2) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C32 C31 C30 119.2(2) . . ?
C32 C31 N4 120.8(2) . . ?
C30 C31 N4 120.0(2) . . ?
C33 C32 C31 120.3(2) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C32 C33 C28 121.4(2) . . ?
C32 C33 H33 119.3 . . ?
C28 C33 H33 119.3 . . ?

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
C5 N1 C1 C2 -0.4(4) . . . . ?
Cu1 N1 C1 C2 179.0(2) . . . . ?
N1 C1 C2 C3 -0.1(4) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C1 C2 C3 C6 -179.4(2) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
C6 C3 C4 C5 179.2(3) . . . . ?
C1 N1 C5 C4 0.2(4) . . . . ?
Cu1 N1 C5 C4 -179.2(2) . . . . ?
C3 C4 C5 N1 0.5(5) . . . . ?
C2 C3 C6 C11 -146.6(3) . . . . ?
C4 C3 C6 C11 33.3(4) . . . . ?
C2 C3 C6 C7 34.4(4) . . . . ?
C4 C3 C6 C7 -145.7(3) . . . . ?
C11 C6 C7 C8 0.0(4) . . . . ?
C3 C6 C7 C8 179.0(2) . . . . ?
C6 C7 C8 C9 1.1(4) . . . . ?
C7 C8 C9 C10 -0.9(4) . . . . ?
C7 C8 C9 N4 178.6(2) . . . . ?
C20 N4 C9 C10 133.3(3) . . . . ?
C31 N4 C9 C10 -43.3(4) . . . . ?
C20 N4 C9 C8 -46.3(4) . . . . ?
C31 N4 C9 C8 137.2(3) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
N4 C9 C10 C11 -179.8(2) . . . . ?
C9 C10 C11 C6 1.4(4) . . . . ?
C7 C6 C11 C10 -1.3(4) . . . . ?
C3 C6 C11 C10 179.7(2) . . . . ?
C16 N2 C12 C13 0.4(5) . . . . ?
Cu1 N2 C12 C13 -176.5(2) 2_746 . . . ?
N2 C12 C13 C14 0.7(5) . . . . ?
C12 C13 C14 C15 -1.4(5) . . . . ?
C12 C13 C14 C17 179.6(3) . . . . ?
C13 C14 C15 C16 1.1(5) . . . . ?
C17 C14 C15 C16 -179.8(3) . . . . ?
C12 N2 C16 C15 -0.7(5) . . . . ?
Cu1 N2 C16 C15 176.2(3) 2_746 . . . ?
C14 C15 C16 N2 -0.1(5) . . . . ?
C13 C14 C17 C22 -151.2(3) . . . . ?
C15 C14 C17 C22 29.8(4) . . . . ?
C13 C14 C17 C18 30.0(4) . . . . ?
C15 C14 C17 C18 -148.9(3) . . . . ?
C22 C17 C18 C19 -3.5(4) . . . . ?
C14 C17 C18 C19 175.3(3) . . . . ?
C17 C18 C19 C20 1.5(4) . . . . ?
C18 C19 C20 C21 1.8(4) . . . . ?
C18 C19 C20 N4 -177.3(2) . . . . ?
C9 N4 C20 C19 151.0(3) . . . . ?
C31 N4 C20 C19 -32.6(4) . . . . ?
C9 N4 C20 C21 -28.1(4) . . . . ?
C31 N4 C20 C21 148.3(3) . . . . ?
C19 C20 C21 C22 -3.0(4) . . . . ?
N4 C20 C21 C22 176.1(3) . . . . ?
C20 C21 C22 C17 1.0(4) . . . . ?
C18 C17 C22 C21 2.2(4) . . . . ?
C14 C17 C22 C21 -176.6(3) . . . . ?
C27 N3 C23 C24 -0.4(5) . . . . ?
N3 C23 C24 C25 0.7(5) . . . . ?
C23 C24 C25 C26 0.0(4) . . . . ?
C23 C24 C25 C28 180.0(3) . . . . ?
C24 C25 C26 C27 -0.8(4) . . . . ?
C28 C25 C26 C27 179.2(3) . . . . ?
C23 N3 C27 C26 -0.5(5) . . . . ?
C25 C26 C27 N3 1.1(5) . . . . ?
C24 C25 C28 C33 168.3(3) . . . . ?
C26 C25 C28 C33 -11.8(4) . . . . ?
C24 C25 C28 C29 -12.5(4) . . . . ?
C26 C25 C28 C29 167.4(3) . . . . ?
C33 C28 C29 C30 1.2(4) . . . . ?
C25 C28 C29 C30 -178.0(2) . . . . ?
C28 C29 C30 C31 -1.5(4) . . . . ?
C29 C30 C31 C32 0.8(4) . . . . ?
C29 C30 C31 N4 -179.3(2) . . . . ?
C20 N4 C31 C32 -43.5(4) . . . . ?
C9 N4 C31 C32 133.0(3) . . . . ?
C20 N4 C31 C30 136.5(3) . . . . ?
C9 N4 C31 C30 -47.0(4) . . . . ?
C30 C31 C32 C33 0.2(4) . . . . ?
N4 C31 C32 C33 -179.8(2) . . . . ?
C31 C32 C33 C28 -0.5(4) . . . . ?
C29 C28 C33 C32 -0.2(4) . . . . ?
C25 C28 C33 C32 179.0(2) . . . . ?

_refine_diff_density_max         1.859
_refine_diff_density_min         -0.821
_refine_diff_density_rms         0.084



####################################################################### 
# 
# 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_CuNPy3NO3_sx_oP
_database_code_depnum_ccdc_archive 'CCDC 1055959'
_audit_update_record             
;
2015-03-24 deposited with the CCDC.
2015-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        CuNPy3NO3
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34.50 H24 Cu N5.50 O5.62'
_chemical_formula_weight         669.13
_chemical_absolute_configuration ad

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      orthorhombic
_space_group_IT_number           17
_space_group_name_H-M_alt        'P 2 2 21'
_space_group_name_Hall           'P 2c 2'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 2 2 21'
_symmetry_space_group_name_Hall  'P 2c 2'
_symmetry_Int_Tables_number      17

_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+1/2'
'-x, y, -z+1/2'
'x, -y, -z'

_cell_length_a                   9.0770(16)
_cell_length_b                   13.831(2)
_cell_length_c                   32.773(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4114.4(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      25.57

_exptl_crystal_description       balde
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.080
_exptl_crystal_F_000             1374
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.051
_exptl_absorpt_coefficient_mu    0.572
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   
;
 SADABS (Sheldrick, 1996)
;

_diffrn_crystal_treatment        
;
attached with Exxon Paratone N to a nylon loop and quenched 
in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. 
;

_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  APEXII-FR591
_diffrn_measurement_method       ω+φ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            69365
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         1.472
_diffrn_reflns_theta_max         28.363
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10282
_reflns_number_gt                8019
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'APEX (Bruker-AXS,2012)'
_computing_cell_refinement       'SAINT (Bruker-AXS,2012)'
_computing_data_reduction        'SAINT and XPREP (Bruker-AXS,2012)'
_computing_structure_solution    'SIR97 (Altomare, et. al. 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
  ORTEP3 for Windows (Farrugia, L., 1997)
  ORTEPIII  (Burnett, N.M., Johnson,C.K., 1996). 
  WinGX (Farrugia, 1999)
  shelXle (Hbschle,C.B., et al., 2011) 
;
_computing_publication_material  ?

_refine_special_details          Twin
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2P)²+5.0P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.08(4)
_refine_ls_number_reflns         10282
_refine_ls_number_parameters     411
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1290
_refine_ls_R_factor_gt           0.1071
_refine_ls_wR_factor_ref         0.3179
_refine_ls_wR_factor_gt          0.3008
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.000
_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 0.55968(14) 0.21876(10) 0.03274(3) 0.0509(4) Uani 1 1 d . . . . .
N1 N 0.6073(7) 0.2196(5) 0.09060(19) 0.0353(14) Uani 1 1 d . . . . .
N2 N 0.5411(9) 0.6867(5) 0.4972(2) 0.0396(16) Uani 1 1 d . . . . .
N3 N 1.3003(8) -0.1600(5) 0.49060(19) 0.0333(14) Uani 1 1 d . . . . .
N4 N 0.8317(8) 0.2328(5) 0.34272(18) 0.0310(13) Uani 1 1 d . . . . .
C1 C 0.7006(10) 0.2851(7) 0.1055(2) 0.0417(19) Uani 1 1 d . . . . .
H1 H 0.7425 0.3303 0.0870 0.050 Uiso 1 1 calc R U . . .
C2 C 0.7400(9) 0.2914(6) 0.1461(2) 0.0373(17) Uani 1 1 d . . . . .
H2 H 0.8043 0.3413 0.1551 0.045 Uiso 1 1 calc R U . . .
C3 C 0.6844(8) 0.2238(6) 0.1740(2) 0.0324(15) Uani 1 1 d . . . . .
C4 C 0.5865(9) 0.1556(6) 0.1585(2) 0.0334(16) Uani 1 1 d . . . . .
H4 H 0.5437 0.1091 0.1763 0.040 Uiso 1 1 calc R U . . .
C5 C 0.5508(9) 0.1552(6) 0.1171(2) 0.0359(17) Uani 1 1 d . . . . .
H5 H 0.4841 0.1077 0.1073 0.043 Uiso 1 1 calc R U . . .
C6 C 0.7259(8) 0.2267(6) 0.2174(2) 0.0285(14) Uani 1 1 d . . . . .
C7 C 0.7832(10) 0.3082(6) 0.2354(2) 0.0358(17) Uani 1 1 d . . . . .
H7 H 0.7984 0.3646 0.2194 0.043 Uiso 1 1 calc R U . . .
C8 C 0.8195(10) 0.3098(6) 0.2766(2) 0.0344(16) Uani 1 1 d . . . . .
H8 H 0.8582 0.3672 0.2884 0.041 Uiso 1 1 calc R U . . .
C9 C 0.7997(9) 0.2286(6) 0.3005(2) 0.0298(14) Uani 1 1 d . . . . .
C10 C 0.7456(9) 0.1443(6) 0.2831(2) 0.0309(15) Uani 1 1 d . . . . .
H10 H 0.7321 0.0880 0.2993 0.037 Uiso 1 1 calc R U . . .
C11 C 0.7115(9) 0.1433(5) 0.2418(2) 0.0287(14) Uani 1 1 d . . . . .
H11 H 0.6776 0.0850 0.2297 0.034 Uiso 1 1 calc R U . . .
C12 C 0.6877(10) 0.6741(6) 0.4918(3) 0.0382(18) Uani 1 1 d . . . . .
H12 H 0.7541 0.7135 0.5068 0.046 Uiso 1 1 calc R U . . .
C13 C 0.7447(9) 0.6055(6) 0.4650(3) 0.0385(17) Uani 1 1 d . . . . .
H13 H 0.8482 0.5993 0.4614 0.046 Uiso 1 1 calc R U . . .
C14 C 0.6492(9) 0.5469(5) 0.4438(2) 0.0310(15) Uani 1 1 d . . . . .
C15 C 0.4972(10) 0.5578(7) 0.4501(3) 0.043(2) Uani 1 1 d . . . . .
H15 H 0.4284 0.5173 0.4365 0.052 Uiso 1 1 calc R U . . .
C16 C 0.4504(10) 0.6288(6) 0.4767(3) 0.0415(19) Uani 1 1 d . . . . .
H16 H 0.3474 0.6367 0.4807 0.050 Uiso 1 1 calc R U . . .
C17 C 0.7020(8) 0.4681(5) 0.4155(2) 0.0296(15) Uani 1 1 d . . . . .
C18 C 0.8381(9) 0.4256(6) 0.4209(2) 0.0359(17) Uani 1 1 d . . . . .
H18 H 0.9030 0.4501 0.4411 0.043 Uiso 1 1 calc R U . . .
C19 C 0.8818(8) 0.3476(6) 0.3972(2) 0.0345(17) Uani 1 1 d . . . . .
H19 H 0.9729 0.3160 0.4023 0.041 Uiso 1 1 calc R U . . .
C20 C 0.7892(8) 0.3160(5) 0.3656(2) 0.0277(14) Uani 1 1 d . . . . .
C21 C 0.6565(8) 0.3642(5) 0.3574(2) 0.0293(14) Uani 1 1 d . . . . .
H21 H 0.5965 0.3456 0.3350 0.035 Uiso 1 1 calc R U . . .
C22 C 0.6157(9) 0.4385(6) 0.3824(3) 0.0323(16) Uani 1 1 d . . . . .
H22 H 0.5257 0.4713 0.3771 0.039 Uiso 1 1 calc R U . . .
C23 C 1.3551(10) -0.1146(7) 0.4585(3) 0.046(2) Uani 1 1 d . . . . .
H23 H 1.4587 -0.1182 0.4546 0.055 Uiso 1 1 calc R U . . .
C24 C 1.2770(10) -0.0634(7) 0.4306(3) 0.044(2) Uani 1 1 d . . . . .
H24 H 1.3253 -0.0339 0.4081 0.053 Uiso 1 1 calc R U . . .
C25 C 1.1257(8) -0.0548(5) 0.4353(2) 0.0254(13) Uani 1 1 d . . . . .
C26 C 1.0648(10) -0.1053(6) 0.4681(2) 0.0384(16) Uani 1 1 d . . . . .
H26 H 0.9612 -0.1044 0.4723 0.046 Uiso 1 1 calc R U . . .
C27 C 1.1512(10) -0.1555(7) 0.4941(2) 0.0413(19) Uani 1 1 d . . . . .
H27 H 1.1056 -0.1895 0.5159 0.050 Uiso 1 1 calc R U . . .
C28 C 1.0407(7) 0.0106(5) 0.4091(2) 0.0252(13) Uani 1 1 d . . . . .
C29 C 1.0766(8) 0.0284(5) 0.3681(2) 0.0278(14) Uani 1 1 d . . . . .
H29 H 1.1518 -0.0090 0.3556 0.033 Uiso 1 1 calc R U . . .
C30 C 1.0065(9) 0.0980(5) 0.3457(2) 0.0301(15) Uani 1 1 d . . . . .
H30 H 1.0338 0.1087 0.3181 0.036 Uiso 1 1 calc R U . . .
C31 C 0.8944(8) 0.1538(5) 0.3635(2) 0.0300(15) Uani 1 1 d . . . . .
C32 C 0.8467(9) 0.1303(6) 0.4032(2) 0.0318(15) Uani 1 1 d . . . . .
H32 H 0.7637 0.1620 0.4147 0.038 Uiso 1 1 calc R U . . .
C33 C 0.9203(8) 0.0617(6) 0.4251(2) 0.0319(15) Uani 1 1 d . . . . .
H33 H 0.8889 0.0481 0.4522 0.038 Uiso 1 1 calc R U . . .
O1N O 0.4248(13) 0.0675(8) 0.0377(4) 0.039(2) Uiso 0.5 1 d . . P A -1
O2N O 0.2963(18) 0.0975(13) -0.0161(5) 0.051(3) Uiso 0.5 1 d . . P A -1
O3N O 0.3124(19) -0.0531(13) 0.0086(6) 0.055(4) Uiso 0.5 1 d . . P A -1
N1N N 0.3455(18) 0.0422(11) 0.0088(5) 0.039(3) Uiso 0.5 1 d . . P A -1
O4N O 0.907(2) 0.5607(8) 0.0001(6) 0.103(7) Uiso 0.5 1 d G . P B -2
O5N O 0.891(2) 0.4269(11) -0.0294(4) 0.074(5) Uiso 0.5 1 d G . P B -2
O6N O 0.840(2) 0.4371(12) 0.0337(4) 0.095(6) Uiso 0.5 1 d G . P B -2
N2N N 0.8709(10) 0.4753(7) 0.0010(3) 0.042(4) Uiso 0.5 1 d G . P B -2
O1D O 1.047(5) 0.435(4) -0.1928(14) 0.230(14) Uiso 0.5 1 d G . P C 3
N1D N 0.902(4) 0.458(3) -0.1374(11) 0.230(14) Uiso 0.5 1 d G . P C 3
C1D C 0.990(5) 0.488(3) -0.1668(14) 0.230(14) Uiso 0.5 1 d G . P C 3
C2D C 0.866(9) 0.356(4) -0.1337(19) 0.230(14) Uiso 0.5 1 d G . P C 3
C3D C 0.840(8) 0.524(4) -0.1077(18) 0.230(14) Uiso 0.5 1 d G . P C 3
O1S O 0.885(3) 0.497(2) -0.1768(9) 0.054(7) Uiso 0.25 1 d . . P D 4
O2S O 0.319(4) 0.085(2) -0.1324(9) 0.057(7) Uiso 0.25 1 d . . P . .
O3S O 0.412(3) 0.1589(16) -0.1358(7) 0.038(5) Uiso 0.25 1 d . . P . .
O4S O 0.399(3) 0.244(2) -0.1206(9) 0.054(7) Uiso 0.25 1 d . . P . .
O5S O 0.296(5) 0.193(3) -0.1308(12) 0.079(10) Uiso 0.25 1 d . . P . .
O6S O 0.141(8) 0.161(5) -0.240(2) 0.13(2) Uiso 0.25 1 d . . P . .
O7S O 0.018(4) 0.153(3) -0.2334(10) 0.066(8) Uiso 0.25 1 d . . P . .
O8S O 0.0000 0.073(4) -0.2500 0.067(12) Uiso 0.25 2 d S . P . .
O9S O 0.502(5) 0.441(3) -0.2323(11) 0.074(9) Uiso 0.25 1 d . . P . .


_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 N1 1.945(6) . ?
Cu1 N2 1.976(7) 2_664 ?
Cu1 N3 2.045(6) 2_754 ?
Cu1 O1N 2.430(12) . ?
N1 C1 1.333(13) . ?
N1 C5 1.346(11) . ?
N2 C16 1.330(12) . ?
N2 C12 1.354(12) . ?
N2 Cu1 1.976(7) 2_665 ?
N3 C23 1.322(11) . ?
N3 C27 1.360(11) . ?
N3 Cu1 2.045(6) 2_755 ?
N4 C31 1.407(9) . ?
N4 C9 1.414(8) . ?
N4 C20 1.427(9) . ?
C1 C2 1.382(12) . ?
C1 H1 0.9500 . ?
C2 C3 1.401(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(12) . ?
C3 C6 1.472(9) . ?
C4 C5 1.395(10) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.374(12) . ?
C6 C11 1.410(10) . ?
C7 C8 1.389(11) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(11) . ?
C10 C11 1.390(10) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.392(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.375(12) . ?
C13 H13 0.9500 . ?
C14 C15 1.404(12) . ?
C14 C17 1.510(10) . ?
C15 C16 1.380(12) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.380(11) . ?
C17 C22 1.399(11) . ?
C18 C19 1.385(11) . ?
C18 H18 0.9500 . ?
C19 C20 1.404(10) . ?
C19 H19 0.9500 . ?
C20 C21 1.403(10) . ?
C21 C22 1.365(11) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.357(12) . ?
C23 H23 0.9500 . ?
C24 C25 1.388(11) . ?
C24 H24 0.9500 . ?
C25 C26 1.398(10) . ?
C25 C28 1.466(10) . ?
C26 C27 1.348(12) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C33 1.404(10) . ?
C28 C29 1.404(10) . ?
C29 C30 1.368(11) . ?
C29 H29 0.9500 . ?
C30 C31 1.403(10) . ?
C30 H30 0.9500 . ?
C31 C32 1.411(10) . ?
C32 C33 1.363(11) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
O1N N1N 1.24(2) . ?
O2N N1N 1.20(2) . ?
O3N N1N 1.35(2) . ?
O4N N2N 1.2250 . ?
O5N N2N 1.2168 . ?
O6N N2N 1.2284 . ?
O1D C1D 1.2304 . ?
N1D C1D 1.3239 . ?
N1D C2D 1.4481 . ?
N1D C3D 1.4514 . ?
O2S O3S 1.33(4) . ?
O2S O5S 1.51(5) . ?
O3S O5S 1.17(5) . ?
O3S O4S 1.28(4) . ?
O4S O5S 1.22(5) . ?
O6S O7S 1.15(7) . ?
O6S O7S 1.68(8) 3_554 ?
O6S O8S 1.80(7) . ?
O7S O7S 1.13(7) 3_554 ?
O7S O8S 1.25(5) . ?
O7S O6S 1.68(8) 3_554 ?
O8S O7S 1.25(5) 3_554 ?
O8S O6S 1.80(7) 3_554 ?
O9S O9S 1.16(7) 3_654 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N2 132.4(3) . 2_664 ?
N1 Cu1 N3 121.5(3) . 2_754 ?
N2 Cu1 N3 98.8(3) 2_664 2_754 ?
N1 Cu1 O1N 93.0(4) . . ?
N2 Cu1 O1N 112.1(4) 2_664 . ?
N3 Cu1 O1N 90.9(3) 2_754 . ?
C1 N1 C5 117.1(7) . . ?
C1 N1 Cu1 120.1(6) . . ?
C5 N1 Cu1 122.8(6) . . ?
C16 N2 C12 117.7(7) . . ?
C16 N2 Cu1 114.1(6) . 2_665 ?
C12 N2 Cu1 128.2(6) . 2_665 ?
C23 N3 C27 114.8(7) . . ?
C23 N3 Cu1 119.5(6) . 2_755 ?
C27 N3 Cu1 125.5(6) . 2_755 ?
C31 N4 C9 121.6(6) . . ?
C31 N4 C20 118.7(6) . . ?
C9 N4 C20 119.5(6) . . ?
N1 C1 C2 124.0(8) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C1 C2 C3 119.5(9) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 116.5(7) . . ?
C4 C3 C6 122.3(7) . . ?
C2 C3 C6 121.2(8) . . ?
C3 C4 C5 120.3(8) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N1 C5 C4 122.5(8) . . ?
N1 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C7 C6 C11 117.5(6) . . ?
C7 C6 C3 122.3(7) . . ?
C11 C6 C3 120.1(7) . . ?
C6 C7 C8 121.3(7) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 120.6(7) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 119.7(6) . . ?
C8 C9 N4 119.7(7) . . ?
C10 C9 N4 120.6(7) . . ?
C9 C10 C11 119.2(7) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C10 C11 C6 121.6(7) . . ?
C10 C11 H11 119.2 . . ?
C6 C11 H11 119.2 . . ?
N2 C12 C13 122.4(8) . . ?
N2 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C14 C13 C12 119.1(8) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 118.8(7) . . ?
C13 C14 C17 122.4(7) . . ?
C15 C14 C17 118.7(7) . . ?
C16 C15 C14 118.2(8) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
N2 C16 C15 123.8(8) . . ?
N2 C16 H16 118.1 . . ?
C15 C16 H16 118.1 . . ?
C18 C17 C22 118.4(7) . . ?
C18 C17 C14 120.9(7) . . ?
C22 C17 C14 120.7(7) . . ?
C17 C18 C19 121.1(7) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C18 C19 C20 118.9(7) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C21 C20 C19 120.5(6) . . ?
C21 C20 N4 120.9(6) . . ?
C19 C20 N4 118.5(6) . . ?
C22 C21 C20 118.4(7) . . ?
C22 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?
C21 C22 C17 122.2(7) . . ?
C21 C22 H22 118.9 . . ?
C17 C22 H22 118.9 . . ?
N3 C23 C24 126.0(8) . . ?
N3 C23 H23 117.0 . . ?
C24 C23 H23 117.0 . . ?
C23 C24 C25 119.1(8) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C24 C25 C26 115.7(7) . . ?
C24 C25 C28 120.6(7) . . ?
C26 C25 C28 123.5(7) . . ?
C27 C26 C25 120.9(8) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 N3 123.4(8) . . ?
C26 C27 H27 118.3 . . ?
N3 C27 H27 118.3 . . ?
C33 C28 C29 116.7(6) . . ?
C33 C28 C25 120.1(6) . . ?
C29 C28 C25 123.1(6) . . ?
C30 C29 C28 121.9(7) . . ?
C30 C29 H29 119.1 . . ?
C28 C29 H29 119.1 . . ?
C29 C30 C31 120.2(7) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C30 C31 N4 121.4(7) . . ?
C30 C31 C32 118.5(7) . . ?
N4 C31 C32 120.1(7) . . ?
C33 C32 C31 119.8(7) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C32 C33 C28 122.4(7) . . ?
C32 C33 H33 118.8 . . ?
C28 C33 H33 118.8 . . ?
N1N O1N Cu1 118.9(10) . . ?
O2N N1N O1N 123.7(16) . . ?
O2N N1N O3N 122(2) . . ?
O1N N1N O3N 114.0(18) . . ?
O5N N2N O4N 118.1 . . ?
O5N N2N O6N 121.0 . . ?
O4N N2N O6N 119.8 . . ?
C1D N1D C2D 120.1 . . ?
C1D N1D C3D 121.8 . . ?
C2D N1D C3D 118.1 . . ?
O1D C1D N1D 125.0 . . ?
O3S O2S O5S 48(2) . . ?
O5S O3S O4S 59(3) . . ?
O5S O3S O2S 74(3) . . ?
O4S O3S O2S 128(3) . . ?
O5S O4S O3S 56(2) . . ?
O3S O5S O4S 65(3) . . ?
O3S O5S O2S 58(2) . . ?
O4S O5S O2S 118(4) . . ?
O7S O6S O7S 42(4) . 3_554 ?
O7S O6S O8S 44(3) . . ?
O7S O6S O8S 42(2) 3_554 . ?
O7S O7S O6S 95(6) 3_554 . ?
O7S O7S O8S 63.1(18) 3_554 . ?
O6S O7S O8S 97(5) . . ?
O7S O7S O6S 43(3) 3_554 3_554 ?
O6S O7S O6S 137(4) . 3_554 ?
O8S O7S O6S 74(3) . 3_554 ?
O7S O8S O7S 54(4) . 3_554 ?
O7S O8S O6S 39(3) . . ?
O7S O8S O6S 64(3) 3_554 . ?
O7S O8S O6S 64(3) . 3_554 ?
O7S O8S O6S 39(3) 3_554 3_554 ?
O6S O8S O6S 94(5) . 3_554 ?

_refine_diff_density_max         1.328
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.185

####################################################################### 
# 
# 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_CuNPy3NO3_sx_op_sq
_database_code_depnum_ccdc_archive 'CCDC 1055960'
_audit_update_record             
;
2015-03-24 deposited with the CCDC.
2015-05-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        CuNPy3NO3
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H24 Cu N5 O3'
_chemical_formula_weight         602.11
_chemical_absolute_configuration ad

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      orthorhombic
_space_group_IT_number           17
_space_group_name_H-M_alt        'P 2 2 21'
_space_group_name_Hall           'P 2c 2'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 2 2 21'
_symmetry_space_group_name_Hall  'P 2c 2'
_symmetry_Int_Tables_number      17

_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+1/2'
'-x, y, -z+1/2'
'x, -y, -z'

_cell_length_a                   9.0770(16)
_cell_length_b                   13.831(2)
_cell_length_c                   32.773(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4114.4(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      25.57

_exptl_crystal_description       blade
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.972
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.051
_exptl_absorpt_coefficient_mu    0.561
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   
;
 SADABS (Sheldrick, 1996)
;

_diffrn_crystal_treatment        
;
attached with Exxon Paratone N to a nylon loop and quenched 
in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. 
;

_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  APEXII-FR591
_diffrn_measurement_method       ω+φ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            69365
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_av_R_equivalents  0.0754
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         1.472
_diffrn_reflns_theta_max         28.363
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10282
_reflns_number_gt                8019
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.790
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_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       'APEX (Bruker-AXS,2012)'
_computing_cell_refinement       'SAINT (Bruker-AXS,2012)'
_computing_data_reduction        'SAINT and XPREP (Bruker-AXS,2012)'
_computing_structure_solution    'ShelxT (sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
  ORTEP3 for Windows (Farrugia, L., 1997)
  ORTEPIII  (Burnett, N.M., Johnson,C.K., 1996). 
  WinGX (Farrugia, 1999)
  shelXle (Hbschle,C.B., et al., 2011) 
;
_computing_publication_material  ?

_refine_special_details          'Twin, SQUEEZE'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.06P)²+1.50P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.063(17)
_refine_ls_number_reflns         10282
_refine_ls_number_parameters     364
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1383
_refine_ls_wR_factor_gt          0.1316
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_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 0.56007(7) 0.21888(5) 0.03269(2) 0.0520(2) Uani 1 1 d . . . . .
N1 N 0.6077(4) 0.2198(3) 0.09060(9) 0.0361(8) Uani 1 1 d . . . . .
N2 N 0.5406(4) 0.6867(2) 0.49713(10) 0.0384(8) Uani 1 1 d . . . . .
N3 N 1.3000(4) -0.1594(3) 0.49103(10) 0.0348(8) Uani 1 1 d . . . . .
N4 N 0.8318(4) 0.2330(2) 0.34279(9) 0.0317(7) Uani 1 1 d . . . . .
C1 C 0.7004(5) 0.2862(4) 0.10557(12) 0.0394(10) Uani 1 1 d . . . . .
H1 H 0.7410 0.3323 0.0873 0.047 Uiso 1 1 calc R U . . .
C2 C 0.7397(4) 0.2913(3) 0.14587(12) 0.0350(9) Uani 1 1 d . . . . .
H2 H 0.8049 0.3406 0.1548 0.042 Uiso 1 1 calc R U . . .
C3 C 0.6849(4) 0.2245(3) 0.17382(10) 0.0322(8) Uani 1 1 d . . . . .
C4 C 0.5863(4) 0.1555(3) 0.15830(12) 0.0337(9) Uani 1 1 d . . . . .
H4 H 0.5428 0.1092 0.1760 0.040 Uiso 1 1 calc R U . . .
C5 C 0.5532(5) 0.1555(3) 0.11722(11) 0.0350(9) Uani 1 1 d . . . . .
H5 H 0.4881 0.1072 0.1072 0.042 Uiso 1 1 calc R U . . .
C6 C 0.7258(4) 0.2270(3) 0.21728(10) 0.0287(8) Uani 1 1 d . . . . .
C7 C 0.7824(5) 0.3082(3) 0.23528(12) 0.0364(9) Uani 1 1 d . . . . .
H7 H 0.7970 0.3646 0.2193 0.044 Uiso 1 1 calc R U . . .
C8 C 0.8191(5) 0.3100(3) 0.27649(12) 0.0349(9) Uani 1 1 d . . . . .
H8 H 0.8577 0.3674 0.2883 0.042 Uiso 1 1 calc R U . . .
C9 C 0.7996(4) 0.2284(3) 0.30020(10) 0.0289(8) Uani 1 1 d . . . . .
C10 C 0.7454(4) 0.1444(3) 0.28270(11) 0.0295(8) Uani 1 1 d . . . . .
H10 H 0.7327 0.0880 0.2988 0.035 Uiso 1 1 calc R U . . .
C11 C 0.7099(4) 0.1429(3) 0.24176(11) 0.0299(8) Uani 1 1 d . . . . .
H11 H 0.6744 0.0849 0.2298 0.036 Uiso 1 1 calc R U . . .
C12 C 0.6878(5) 0.6743(3) 0.49186(13) 0.0401(10) Uani 1 1 d . . . . .
H12 H 0.7540 0.7136 0.5070 0.048 Uiso 1 1 calc R U . . .
C13 C 0.7444(4) 0.6059(3) 0.46507(13) 0.0356(9) Uani 1 1 d . . . . .
H13 H 0.8478 0.6001 0.4615 0.043 Uiso 1 1 calc R U . . .
C14 C 0.6488(4) 0.5460(3) 0.44354(12) 0.0295(8) Uani 1 1 d . . . . .
C15 C 0.4972(5) 0.5574(3) 0.45018(15) 0.0419(11) Uani 1 1 d . . . . .
H15 H 0.4276 0.5169 0.4369 0.050 Uiso 1 1 calc R U . . .
C16 C 0.4518(5) 0.6296(3) 0.47668(13) 0.0412(10) Uani 1 1 d . . . . .
H16 H 0.3488 0.6384 0.4803 0.049 Uiso 1 1 calc R U . . .
C17 C 0.7016(4) 0.4691(3) 0.41522(12) 0.0302(8) Uani 1 1 d . . . . .
C18 C 0.8378(5) 0.4260(3) 0.42096(13) 0.0367(9) Uani 1 1 d . . . . .
H18 H 0.9021 0.4501 0.4415 0.044 Uiso 1 1 calc R U . . .
C19 C 0.8815(4) 0.3481(3) 0.39718(12) 0.0343(9) Uani 1 1 d . . . . .
H19 H 0.9728 0.3168 0.4022 0.041 Uiso 1 1 calc R U . . .
C20 C 0.7894(4) 0.3164(3) 0.36565(11) 0.0274(8) Uani 1 1 d . . . . .
C21 C 0.6572(4) 0.3642(3) 0.35781(12) 0.0315(8) Uani 1 1 d . . . . .
H21 H 0.5965 0.3446 0.3357 0.038 Uiso 1 1 calc R U . . .
C22 C 0.6156(4) 0.4394(3) 0.38218(12) 0.0323(9) Uani 1 1 d . . . . .
H22 H 0.5260 0.4723 0.3766 0.039 Uiso 1 1 calc R U . . .
C23 C 1.3557(5) -0.1154(4) 0.45861(15) 0.0485(12) Uani 1 1 d . . . . .
H23 H 1.4590 -0.1204 0.4543 0.058 Uiso 1 1 calc R U . . .
C24 C 1.2760(5) -0.0632(3) 0.43080(15) 0.0446(11) Uani 1 1 d . . . . .
H24 H 1.3240 -0.0332 0.4084 0.054 Uiso 1 1 calc R U . . .
C25 C 1.1259(4) -0.0545(3) 0.43546(11) 0.0257(8) Uani 1 1 d . . . . .
C26 C 1.0643(5) -0.1051(3) 0.46764(12) 0.0378(9) Uani 1 1 d . . . . .
H26 H 0.9605 -0.1050 0.4713 0.045 Uiso 1 1 calc R U . . .
C27 C 1.1521(5) -0.1552(3) 0.49411(13) 0.0419(10) Uani 1 1 d . . . . .
H27 H 1.1062 -0.1890 0.5159 0.050 Uiso 1 1 calc R U . . .
C28 C 1.0399(4) 0.0103(3) 0.40900(11) 0.0247(7) Uani 1 1 d . . . . .
C29 C 1.0768(4) 0.0286(3) 0.36813(11) 0.0273(8) Uani 1 1 d . . . . .
H29 H 1.1525 -0.0084 0.3556 0.033 Uiso 1 1 calc R U . . .
C30 C 1.0059(4) 0.0987(3) 0.34580(11) 0.0280(8) Uani 1 1 d . . . . .
H30 H 1.0335 0.1097 0.3182 0.034 Uiso 1 1 calc R U . . .
C31 C 0.8946(4) 0.1533(3) 0.36318(11) 0.0305(8) Uani 1 1 d . . . . .
C32 C 0.8476(4) 0.1307(3) 0.40333(11) 0.0329(9) Uani 1 1 d . . . . .
H32 H 0.7657 0.1635 0.4150 0.039 Uiso 1 1 calc R U . . .
C33 C 0.9208(4) 0.0616(3) 0.42513(11) 0.0338(9) Uani 1 1 d . . . . .
H33 H 0.8896 0.0479 0.4522 0.041 Uiso 1 1 calc R U . . .
O1N O 0.4252(6) 0.0680(3) 0.03644(14) 0.0409(13) Uiso 0.5 1 d G . P A -1
O2N O 0.2984(7) 0.0937(3) -0.01581(15) 0.0470(16) Uiso 0.5 1 d G . P A -1
O3N O 0.3181(7) -0.0496(3) 0.00722(17) 0.0550(18) Uiso 0.5 1 d G . P A -1
N1N N 0.3399(3) 0.0377(3) 0.01043(11) 0.0462(19) Uiso 0.5 1 d G . P A -1
O4N O 0.9060(11) 0.5621(4) -0.0011(3) 0.109(4) Uiso 0.5 1 d G . P B -2
O5N O 0.8917(9) 0.4269(5) -0.02960(19) 0.076(2) Uiso 0.5 1 d G . P B -2
O6N O 0.8408(10) 0.4398(6) 0.03355(19) 0.096(3) Uiso 0.5 1 d G . P B -2
N2N N 0.8712(4) 0.4766(4) 0.00051(17) 0.0469(19) Uiso 0.5 1 d G . P B -2


_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 N1 1.946(3) . ?
Cu1 N2 1.975(3) 2_664 ?
Cu1 N3 2.039(3) 2_754 ?
Cu1 O1N 2.423(5) . ?
N1 C1 1.339(6) . ?
N1 C5 1.340(5) . ?
N2 C16 1.312(6) . ?
N2 C12 1.358(6) . ?
N2 Cu1 1.975(3) 2_665 ?
N3 C23 1.325(6) . ?
N3 C27 1.348(6) . ?
N3 Cu1 2.038(3) 2_755 ?
N4 C31 1.409(5) . ?
N4 C9 1.427(4) . ?
N4 C20 1.428(5) . ?
C1 C2 1.370(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.393(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.403(6) . ?
C3 C6 1.472(5) . ?
C4 C5 1.380(5) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.368(6) . ?
C6 C11 1.420(5) . ?
C7 C8 1.391(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(6) . ?
C10 C11 1.380(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.388(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.403(6) . ?
C14 C17 1.491(5) . ?
C15 C16 1.386(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.385(6) . ?
C17 C22 1.397(6) . ?
C18 C19 1.387(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.400(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.395(5) . ?
C21 C22 1.364(5) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.370(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.376(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.384(5) . ?
C25 C28 1.472(5) . ?
C26 C27 1.366(6) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C33 1.397(5) . ?
C28 C29 1.404(5) . ?
C29 C30 1.375(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.384(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.418(5) . ?
C32 C33 1.367(5) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
O1N N1N 1.2250 . ?
O2N N1N 1.2169 . ?
O3N N1N 1.2283 . ?
O4N N2N 1.2251 . ?
O5N N2N 1.2169 . ?
O6N N2N 1.2283 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N2 132.37(14) . 2_664 ?
N1 Cu1 N3 121.15(13) . 2_754 ?
N2 Cu1 N3 99.21(14) 2_664 2_754 ?
N1 Cu1 O1N 93.92(16) . . ?
N2 Cu1 O1N 111.47(15) 2_664 . ?
N3 Cu1 O1N 90.06(17) 2_754 . ?
C1 N1 C5 116.6(3) . . ?
C1 N1 Cu1 120.1(3) . . ?
C5 N1 Cu1 123.3(3) . . ?
C16 N2 C12 117.6(3) . . ?
C16 N2 Cu1 114.5(3) . 2_665 ?
C12 N2 Cu1 127.9(3) . 2_665 ?
C23 N3 C27 114.9(4) . . ?
C23 N3 Cu1 119.0(3) . 2_755 ?
C27 N3 Cu1 126.0(3) . 2_755 ?
C31 N4 C9 120.8(3) . . ?
C31 N4 C20 119.4(3) . . ?
C9 N4 C20 119.6(3) . . ?
N1 C1 C2 123.5(4) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C1 C2 C3 120.5(4) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 116.1(3) . . ?
C2 C3 C6 122.0(4) . . ?
C4 C3 C6 121.9(4) . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 123.7(4) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C7 C6 C11 117.8(3) . . ?
C7 C6 C3 122.1(4) . . ?
C11 C6 C3 120.1(4) . . ?
C6 C7 C8 121.6(4) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C9 C8 C7 120.0(4) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 119.8(3) . . ?
C8 C9 N4 119.2(3) . . ?
C10 C9 N4 120.9(3) . . ?
C11 C10 C9 119.9(4) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C6 120.9(4) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
N2 C12 C13 122.0(4) . . ?
N2 C12 H12 119.0 . . ?
C13 C12 H12 119.0 . . ?
C12 C13 C14 119.7(4) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 117.8(4) . . ?
C13 C14 C17 122.7(4) . . ?
C15 C14 C17 119.5(4) . . ?
C16 C15 C14 118.1(4) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
N2 C16 C15 124.8(4) . . ?
N2 C16 H16 117.6 . . ?
C15 C16 H16 117.6 . . ?
C18 C17 C22 118.5(3) . . ?
C18 C17 C14 120.6(4) . . ?
C22 C17 C14 120.8(4) . . ?
C17 C18 C19 120.9(4) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C20 119.2(4) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
C21 C20 C19 120.1(3) . . ?
C21 C20 N4 121.2(3) . . ?
C19 C20 N4 118.7(3) . . ?
C22 C21 C20 119.5(4) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C17 121.5(4) . . ?
C21 C22 H22 119.2 . . ?
C17 C22 H22 119.2 . . ?
N3 C23 C24 125.0(4) . . ?
N3 C23 H23 117.5 . . ?
C24 C23 H23 117.5 . . ?
C23 C24 C25 119.7(4) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C26 116.2(4) . . ?
C24 C25 C28 120.9(4) . . ?
C26 C25 C28 122.8(3) . . ?
C27 C26 C25 120.3(4) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
N3 C27 C26 123.7(4) . . ?
N3 C27 H27 118.1 . . ?
C26 C27 H27 118.1 . . ?
C33 C28 C29 117.0(3) . . ?
C33 C28 C25 119.8(3) . . ?
C29 C28 C25 123.0(3) . . ?
C30 C29 C28 121.6(3) . . ?
C30 C29 H29 119.2 . . ?
C28 C29 H29 119.2 . . ?
C29 C30 C31 120.5(3) . . ?
C29 C30 H30 119.7 . . ?
C31 C30 H30 119.7 . . ?
C30 C31 N4 121.8(3) . . ?
C30 C31 C32 118.8(3) . . ?
N4 C31 C32 119.4(3) . . ?
C33 C32 C31 119.5(4) . . ?
C33 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
C32 C33 C28 122.3(3) . . ?
C32 C33 H33 118.9 . . ?
C28 C33 H33 118.9 . . ?
N1N O1N Cu1 125.3(2) . . ?
O2N N1N O1N 118.1 . . ?
O2N N1N O3N 121.0 . . ?
O1N N1N O3N 119.8 . . ?
O5N N2N O4N 118.1 . . ?
O5N N2N O6N 121.0 . . ?
O4N N2N O6N 119.8 . . ?

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
C5 N1 C1 C2 -0.4(6) . . . . ?
Cu1 N1 C1 C2 -179.7(3) . . . . ?
N1 C1 C2 C3 0.9(6) . . . . ?
C1 C2 C3 C4 -1.6(6) . . . . ?
C1 C2 C3 C6 179.4(4) . . . . ?
C2 C3 C4 C5 1.9(6) . . . . ?
C6 C3 C4 C5 -179.1(4) . . . . ?
C1 N1 C5 C4 0.7(6) . . . . ?
Cu1 N1 C5 C4 180.0(3) . . . . ?
C3 C4 C5 N1 -1.5(6) . . . . ?
C2 C3 C6 C7 19.7(6) . . . . ?
C4 C3 C6 C7 -159.3(4) . . . . ?
C2 C3 C6 C11 -159.0(4) . . . . ?
C4 C3 C6 C11 22.0(6) . . . . ?
C11 C6 C7 C8 -2.0(6) . . . . ?
C3 C6 C7 C8 179.3(4) . . . . ?
C6 C7 C8 C9 0.4(6) . . . . ?
C7 C8 C9 C10 1.0(6) . . . . ?
C7 C8 C9 N4 -177.3(4) . . . . ?
C31 N4 C9 C8 -143.6(4) . . . . ?
C20 N4 C9 C8 41.3(5) . . . . ?
C31 N4 C9 C10 38.2(5) . . . . ?
C20 N4 C9 C10 -136.9(4) . . . . ?
C8 C9 C10 C11 -0.6(6) . . . . ?
N4 C9 C10 C11 177.6(4) . . . . ?
C9 C10 C11 C6 -1.1(6) . . . . ?
C7 C6 C11 C10 2.3(6) . . . . ?
C3 C6 C11 C10 -178.9(3) . . . . ?
C16 N2 C12 C13 1.8(6) . . . . ?
Cu1 N2 C12 C13 -178.6(3) 2_665 . . . ?
N2 C12 C13 C14 -1.7(7) . . . . ?
C12 C13 C14 C15 -0.3(6) . . . . ?
C12 C13 C14 C17 -178.1(4) . . . . ?
C13 C14 C15 C16 2.1(7) . . . . ?
C17 C14 C15 C16 180.0(4) . . . . ?
C12 N2 C16 C15 0.2(6) . . . . ?
Cu1 N2 C16 C15 -179.5(4) 2_665 . . . ?
C14 C15 C16 N2 -2.1(7) . . . . ?
C13 C14 C17 C18 27.2(6) . . . . ?
C15 C14 C17 C18 -150.6(4) . . . . ?
C13 C14 C17 C22 -152.3(4) . . . . ?
C15 C14 C17 C22 29.9(6) . . . . ?
C22 C17 C18 C19 -6.7(6) . . . . ?
C14 C17 C18 C19 173.7(4) . . . . ?
C17 C18 C19 C20 3.3(6) . . . . ?
C18 C19 C20 C21 1.5(6) . . . . ?
C18 C19 C20 N4 -176.7(4) . . . . ?
C31 N4 C20 C21 -137.8(4) . . . . ?
C9 N4 C20 C21 37.4(5) . . . . ?
C31 N4 C20 C19 40.3(5) . . . . ?
C9 N4 C20 C19 -144.5(4) . . . . ?
C19 C20 C21 C22 -2.8(6) . . . . ?
N4 C20 C21 C22 175.3(4) . . . . ?
C20 C21 C22 C17 -0.7(6) . . . . ?
C18 C17 C22 C21 5.5(6) . . . . ?
C14 C17 C22 C21 -175.0(4) . . . . ?
C27 N3 C23 C24 4.1(7) . . . . ?
Cu1 N3 C23 C24 -172.3(4) 2_755 . . . ?
N3 C23 C24 C25 -0.5(8) . . . . ?
C23 C24 C25 C26 -3.5(7) . . . . ?
C23 C24 C25 C28 172.7(4) . . . . ?
C24 C25 C26 C27 3.8(6) . . . . ?
C28 C25 C26 C27 -172.3(4) . . . . ?
C23 N3 C27 C26 -3.7(7) . . . . ?
Cu1 N3 C27 C26 172.4(3) 2_755 . . . ?
C25 C26 C27 N3 -0.2(7) . . . . ?
C24 C25 C28 C33 -143.3(4) . . . . ?
C26 C25 C28 C33 32.6(6) . . . . ?
C24 C25 C28 C29 32.5(6) . . . . ?
C26 C25 C28 C29 -151.6(4) . . . . ?
C33 C28 C29 C30 4.5(5) . . . . ?
C25 C28 C29 C30 -171.5(4) . . . . ?
C28 C29 C30 C31 -0.3(6) . . . . ?
C29 C30 C31 N4 172.5(4) . . . . ?
C29 C30 C31 C32 -4.7(6) . . . . ?
C9 N4 C31 C30 41.4(6) . . . . ?
C20 N4 C31 C30 -143.4(4) . . . . ?
C9 N4 C31 C32 -141.4(4) . . . . ?
C20 N4 C31 C32 33.8(5) . . . . ?
C30 C31 C32 C33 5.5(6) . . . . ?
N4 C31 C32 C33 -171.8(4) . . . . ?
C31 C32 C33 C28 -1.2(6) . . . . ?
C29 C28 C33 C32 -3.7(6) . . . . ?
C25 C28 C33 C32 172.4(4) . . . . ?
Cu1 O1N N1N O2N -13.8(5) . . . . ?
Cu1 O1N N1N O3N 154.1(5) . . . . ?

_refine_diff_density_max         0.751
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.056



