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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_complex1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 Cu N2 O6'
_chemical_formula_weight         343.78

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9254(18)
_cell_length_b                   9.0881(18)
_cell_length_c                   9.652(2)
_cell_angle_alpha                110.363(4)
_cell_angle_beta                 97.535(4)
_cell_angle_gamma                105.761(4)
_cell_volume                     684.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8234
_cell_measurement_theta_min      2.759
_cell_measurement_theta_max      34.194

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.45
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             350
_exptl_absorpt_coefficient_mu    1.626
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.4970
_exptl_absorpt_correction_T_max  0.5282
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6459
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2417
_reflns_number_gt                2082
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER AXS SMART 3'
_computing_cell_refinement       'BRUKER AXS SMART 3'
_computing_data_reduction        'BRUKER AXS SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'BRUKER SHELXLTL'
_computing_publication_material  'MERCURY 1.4'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0387P)²+0.3239P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2417
_refine_ls_number_parameters     190
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0798
_refine_ls_wR_factor_gt          0.0765
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.185
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.70909(4) 0.94816(5) 0.81400(4) 0.03071(15) Uani 1 1 d . . .
O2 O 0.8809(3) 1.1238(3) 0.9933(2) 0.0376(5) Uani 1 1 d . . .
O1 O 0.6038(3) 0.8577(3) 0.9495(2) 0.0370(5) Uani 1 1 d . . .
N2 N 0.5424(3) 0.7796(3) 0.6237(3) 0.0322(6) Uani 1 1 d . . .
C6 C 0.5585(4) 0.8037(4) 0.4958(3) 0.0315(7) Uani 1 1 d . . .
N1 N 0.7907(3) 1.0325(3) 0.6635(3) 0.0323(6) Uani 1 1 d . . .
C5 C 0.7020(4) 0.9466(4) 0.5182(3) 0.0312(7) Uani 1 1 d . . .
C4 C 0.7443(4) 0.9916(5) 0.4027(4) 0.0441(9) Uani 1 1 d . . .
H4 H 0.6820 0.9313 0.3028 0.053 Uiso 1 1 calc R . .
C7 C 0.4491(4) 0.7028(4) 0.3567(4) 0.0438(9) Uani 1 1 d . . .
H7 H 0.4623 0.7226 0.2700 0.053 Uiso 1 1 calc R . .
C1 C 0.9223(4) 1.1641(4) 0.6947(4) 0.0439(8) Uani 1 1 d . . .
H1 H 0.9840 1.2232 0.7949 0.053 Uiso 1 1 calc R . .
C10 C 0.4158(4) 0.6519(4) 0.6134(4) 0.0427(8) Uani 1 1 d . . .
H10 H 0.4033 0.6342 0.7011 0.051 Uiso 1 1 calc R . .
C3 C 0.8805(5) 1.1274(5) 0.4372(5) 0.0533(10) Uani 1 1 d . . .
H3 H 0.9114 1.1591 0.3606 0.064 Uiso 1 1 calc R . .
C8 C 0.3206(5) 0.5728(5) 0.3481(4) 0.0525(10) Uani 1 1 d . . .
H8 H 0.2455 0.5033 0.2557 0.063 Uiso 1 1 calc R . .
C2 C 0.9693(5) 1.2148(5) 0.5847(5) 0.0537(10) Uani 1 1 d . . .
H2 H 1.0605 1.3076 0.6100 0.064 Uiso 1 1 calc R . .
C9 C 0.3053(4) 0.5474(5) 0.4784(4) 0.0511(10) Uani 1 1 d . . .
H9 H 0.2198 0.4594 0.4748 0.061 Uiso 1 1 calc R . .
O4 O 0.5517(3) 1.1115(3) 0.8887(2) 0.0370(5) Uani 1 1 d . . .
O3 O 0.8987(3) 0.8221(3) 0.8334(2) 0.0372(5) Uani 1 1 d . . .
C11 C 0.9964(4) 1.0880(4) 1.0476(3) 0.0297(7) Uani 1 1 d . . .
C12 C 0.5139(4) 0.9265(4) 1.0185(3) 0.0297(7) Uani 1 1 d . . .
O6 O 0.6559(4) 0.6104(4) 1.0550(4) 0.0856(10) Uani 1 1 d GD . .
H333 H 0.6320 0.6984 1.0190 0.128 Uiso 1 1 d GD . .
H444 H 0.7041 0.5483 1.0647 0.128 Uiso 1 1 d GD . .
O5 O 0.8754(5) 1.4559(4) 1.0644(7) 0.170(3) Uani 1 1 d GD . .
H222 H 0.8670 1.4153 0.9674 0.255 Uiso 1 1 d GD . .
H111 H 0.8563 1.4226 1.1303 0.255 Uiso 1 1 d GD . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.979(2) . ?
Cu1 O2 1.987(2) . ?
Cu1 N1 1.994(2) . ?
Cu1 N2 2.005(3) . ?
Cu1 O3 2.309(2) . ?
Cu1 O4 2.313(2) . ?
O2 C11 1.265(4) . ?
O1 C12 1.265(4) . ?
N2 C10 1.346(4) . ?
N2 C6 1.346(4) . ?
C6 C7 1.382(4) . ?
C6 C5 1.484(4) . ?
N1 C1 1.340(4) . ?
N1 C5 1.347(4) . ?
C5 C4 1.377(4) . ?
C4 C3 1.380(5) . ?
C4 H4 0.9300 . ?
C7 C8 1.374(5) . ?
C7 H7 0.9300 . ?
C1 C2 1.367(5) . ?
C1 H1 0.9300 . ?
C10 C9 1.366(5) . ?
C10 H10 0.9300 . ?
C3 C2 1.364(5) . ?
C3 H3 0.9300 . ?
C8 C9 1.373(5) . ?
C8 H8 0.9300 . ?
C2 H2 0.9300 . ?
C9 H9 0.9300 . ?
O4 C12 1.228(4) 2_677 ?
O3 C11 1.230(4) 2_777 ?
C11 O3 1.230(4) 2_777 ?
C11 C11 1.567(6) 2_777 ?
C12 O4 1.228(4) 2_677 ?
C12 C12 1.569(6) 2_677 ?
O6 H333 1.0352 . ?
O6 H444 0.8192 . ?
O5 H222 0.8621 . ?
O5 H111 0.8122 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 90.31(10) . . ?
O1 Cu1 N1 173.64(10) . . ?
O2 Cu1 N1 94.87(10) . . ?
O1 Cu1 N2 93.86(10) . . ?
O2 Cu1 N2 175.78(10) . . ?
N1 Cu1 N2 80.92(10) . . ?
O1 Cu1 O3 90.12(8) . . ?
O2 Cu1 O3 77.43(8) . . ?
N1 Cu1 O3 94.59(9) . . ?
N2 Cu1 O3 103.17(9) . . ?
O1 Cu1 O4 77.80(8) . . ?
O2 Cu1 O4 85.84(9) . . ?
N1 Cu1 O4 98.87(9) . . ?
N2 Cu1 O4 94.41(9) . . ?
O3 Cu1 O4 159.34(8) . . ?
C11 O2 Cu1 119.09(19) . . ?
C12 O1 Cu1 119.07(19) . . ?
C10 N2 C6 118.1(3) . . ?
C10 N2 Cu1 126.8(2) . . ?
C6 N2 Cu1 115.1(2) . . ?
N2 C6 C7 122.0(3) . . ?
N2 C6 C5 114.2(3) . . ?
C7 C6 C5 123.8(3) . . ?
C1 N1 C5 118.7(3) . . ?
C1 N1 Cu1 126.1(2) . . ?
C5 N1 Cu1 115.2(2) . . ?
N1 C5 C4 121.3(3) . . ?
N1 C5 C6 114.5(3) . . ?
C4 C5 C6 124.1(3) . . ?
C5 C4 C3 119.1(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C8 C7 C6 119.1(3) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
N1 C1 C2 122.4(3) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
N2 C10 C9 122.2(3) . . ?
N2 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C9 C8 C7 118.8(3) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C3 C2 C1 119.1(4) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C12 O4 Cu1 108.55(19) 2_677 . ?
C11 O3 Cu1 108.63(19) 2_777 . ?
O3 C11 O2 126.1(3) 2_777 . ?
O3 C11 C11 118.0(3) 2_777 2_777 ?
O2 C11 C11 115.9(3) . 2_777 ?
O4 C12 O1 125.6(3) 2_677 . ?
O4 C12 C12 118.0(3) 2_677 2_677 ?
O1 C12 C12 116.4(3) . 2_677 ?
H333 O6 H444 155.9 . . ?
H222 O5 H111 138.6 . . ?

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
O1 Cu1 O2 C11 81.5(2) . . . . ?
N1 Cu1 O2 C11 -102.2(2) . . . . ?
N2 Cu1 O2 C11 -107.1(13) . . . . ?
O3 Cu1 O2 C11 -8.6(2) . . . . ?
O4 Cu1 O2 C11 159.2(2) . . . . ?
O2 Cu1 O1 C12 81.7(2) . . . . ?
N1 Cu1 O1 C12 -62.9(9) . . . . ?
N2 Cu1 O1 C12 -97.6(2) . . . . ?
O3 Cu1 O1 C12 159.2(2) . . . . ?
O4 Cu1 O1 C12 -3.9(2) . . . . ?
O1 Cu1 N2 C10 -3.2(3) . . . . ?
O2 Cu1 N2 C10 -174.6(12) . . . . ?
N1 Cu1 N2 C10 -179.5(3) . . . . ?
O3 Cu1 N2 C10 87.8(3) . . . . ?
O4 Cu1 N2 C10 -81.2(3) . . . . ?
O1 Cu1 N2 C6 174.1(2) . . . . ?
O2 Cu1 N2 C6 2.8(14) . . . . ?
N1 Cu1 N2 C6 -2.2(2) . . . . ?
O3 Cu1 N2 C6 -94.8(2) . . . . ?
O4 Cu1 N2 C6 96.1(2) . . . . ?
C10 N2 C6 C7 0.5(5) . . . . ?
Cu1 N2 C6 C7 -177.0(2) . . . . ?
C10 N2 C6 C5 -179.6(3) . . . . ?
Cu1 N2 C6 C5 2.8(3) . . . . ?
O1 Cu1 N1 C1 145.7(8) . . . . ?
O2 Cu1 N1 C1 1.3(3) . . . . ?
N2 Cu1 N1 C1 -179.1(3) . . . . ?
O3 Cu1 N1 C1 -76.5(3) . . . . ?
O4 Cu1 N1 C1 87.8(3) . . . . ?
O1 Cu1 N1 C5 -34.0(10) . . . . ?
O2 Cu1 N1 C5 -178.5(2) . . . . ?
N2 Cu1 N1 C5 1.1(2) . . . . ?
O3 Cu1 N1 C5 103.7(2) . . . . ?
O4 Cu1 N1 C5 -92.0(2) . . . . ?
C1 N1 C5 C4 0.0(5) . . . . ?
Cu1 N1 C5 C4 179.8(2) . . . . ?
C1 N1 C5 C6 -179.7(3) . . . . ?
Cu1 N1 C5 C6 0.1(3) . . . . ?
N2 C6 C5 N1 -1.9(4) . . . . ?
C7 C6 C5 N1 178.0(3) . . . . ?
N2 C6 C5 C4 178.4(3) . . . . ?
C7 C6 C5 C4 -1.8(5) . . . . ?
N1 C5 C4 C3 0.1(5) . . . . ?
C6 C5 C4 C3 179.8(3) . . . . ?
N2 C6 C7 C8 -0.6(5) . . . . ?
C5 C6 C7 C8 179.5(3) . . . . ?
C5 N1 C1 C2 0.4(5) . . . . ?
Cu1 N1 C1 C2 -179.4(3) . . . . ?
C6 N2 C10 C9 0.2(5) . . . . ?
Cu1 N2 C10 C9 177.4(3) . . . . ?
C5 C4 C3 C2 -0.5(6) . . . . ?
C6 C7 C8 C9 0.0(6) . . . . ?
C4 C3 C2 C1 0.9(6) . . . . ?
N1 C1 C2 C3 -0.8(6) . . . . ?
N2 C10 C9 C8 -0.8(6) . . . . ?
C7 C8 C9 C10 0.7(6) . . . . ?
O1 Cu1 O4 C12 3.8(2) . . . 2_677 ?
O2 Cu1 O4 C12 -87.4(2) . . . 2_677 ?
N1 Cu1 O4 C12 178.3(2) . . . 2_677 ?
N2 Cu1 O4 C12 96.8(2) . . . 2_677 ?
O3 Cu1 O4 C12 -51.6(3) . . . 2_677 ?
O1 Cu1 O3 C11 -82.4(2) . . . 2_777 ?
O2 Cu1 O3 C11 7.9(2) . . . 2_777 ?
N1 Cu1 O3 C11 101.9(2) . . . 2_777 ?
N2 Cu1 O3 C11 -176.3(2) . . . 2_777 ?
O4 Cu1 O3 C11 -28.7(3) . . . 2_777 ?
Cu1 O2 C11 O3 -171.9(2) . . . 2_777 ?
Cu1 O2 C11 C11 8.0(4) . . . 2_777 ?
Cu1 O1 C12 O4 -176.1(2) . . . 2_677 ?
Cu1 O1 C12 C12 3.6(4) . . . 2_677 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 1002488'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Complex2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 Cu N4 O4'
_chemical_formula_weight         339.80

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '

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

_cell_length_a                   13.4876(14)
_cell_length_b                   11.2653(12)
_cell_length_c                   8.7010(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.755(2)
_cell_angle_gamma                90.00
_cell_volume                     1319.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3345
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.58

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             692
_exptl_absorpt_coefficient_mu    1.678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  .747
_exptl_absorpt_correction_T_max  .791
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6866
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1171
_reflns_number_gt                1096
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0340P)²+1.4688P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1171
_refine_ls_number_parameters     96
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_ref         0.0661
_refine_ls_wR_factor_gt          0.0650
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.65891(3) 0.2500 0.02378(14) Uani 1 2 d S . .
N1 N 0.58587(13) 0.78179(17) 0.1510(2) 0.0297(4) Uani 1 1 d . . .
C6 C 0.54864(14) 0.47584(19) 0.0434(2) 0.0240(4) Uani 1 1 d . . .
C5 C 0.68101(16) 0.8067(2) 0.1954(3) 0.0310(5) Uani 1 1 d . . .
C1 C 0.5474(2) 0.8343(2) 0.0212(4) 0.0520(8) Uani 1 1 d . . .
H1 H 0.4818 0.8178 -0.0109 0.062 Uiso 1 1 calc R . .
C2 C 0.5988(2) 0.9097(3) -0.0652(4) 0.0641(9) Uani 1 1 d . . .
H2 H 0.5689 0.9432 -0.1543 0.077 Uiso 1 1 calc R . .
C4 C 0.73693(17) 0.8862(2) 0.1117(3) 0.0403(6) Uani 1 1 d . . .
H4 H 0.8018 0.9045 0.1463 0.048 Uiso 1 1 calc R . .
C3 C 0.6967(2) 0.9361(2) -0.0186(3) 0.0470(7) Uani 1 1 d . . .
H3 H 0.7337 0.9873 -0.0761 0.056 Uiso 1 1 calc R . .
O1 O 0.58070(10) 0.53059(13) 0.16186(16) 0.0292(3) Uani 1 1 d . . .
O2 O 0.41233(11) 0.61317(14) 0.01098(17) 0.0307(4) Uani 1 1 d . . .
N2 N 0.72181(16) 0.7551(2) 0.3230(2) 0.0543(7) Uani 1 1 d . . .
H2A H 0.6873 0.7072 0.3748 0.065 Uiso 1 1 calc R . .
H2B H 0.7825 0.7700 0.3531 0.065 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9930(15) 2_655 ?
Cu1 O1 1.9930(15) . ?
Cu1 N1 2.0324(18) . ?
Cu1 N1 2.0324(18) 2_655 ?
Cu1 O2 2.3805(15) 2_655 ?
Cu1 O2 2.3805(15) . ?
N1 C5 1.345(3) . ?
N1 C1 1.348(3) . ?
C6 O2 1.241(3) 5_665 ?
C6 O1 1.253(3) . ?
C6 C6 1.568(4) 5_665 ?
C5 N2 1.339(3) . ?
C5 C4 1.405(3) . ?
C1 C2 1.355(4) . ?
C2 C3 1.388(4) . ?
C4 C3 1.347(4) . ?
O2 C6 1.241(3) 5_665 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 87.01(9) 2_655 . ?
O1 Cu1 N1 176.30(7) 2_655 . ?
O1 Cu1 N1 89.44(7) . . ?
O1 Cu1 N1 89.44(7) 2_655 2_655 ?
O1 Cu1 N1 176.30(7) . 2_655 ?
N1 Cu1 N1 94.14(11) . 2_655 ?
O1 Cu1 O2 76.08(5) 2_655 2_655 ?
O1 Cu1 O2 85.79(6) . 2_655 ?
N1 Cu1 O2 104.68(6) . 2_655 ?
N1 Cu1 O2 92.37(6) 2_655 2_655 ?
O1 Cu1 O2 85.79(6) 2_655 . ?
O1 Cu1 O2 76.08(5) . . ?
N1 Cu1 O2 92.37(6) . . ?
N1 Cu1 O2 104.68(6) 2_655 . ?
O2 Cu1 O2 155.00(8) 2_655 . ?
C5 N1 C1 117.2(2) . . ?
C5 N1 Cu1 125.43(15) . . ?
C1 N1 Cu1 117.08(15) . . ?
O2 C6 O1 125.39(18) 5_665 . ?
O2 C6 C6 117.3(2) 5_665 5_665 ?
O1 C6 C6 117.3(2) . 5_665 ?
N2 C5 N1 118.7(2) . . ?
N2 C5 C4 120.1(2) . . ?
N1 C5 C4 121.2(2) . . ?
N1 C1 C2 123.9(2) . . ?
C1 C2 C3 118.9(3) . . ?
C3 C4 C5 120.1(2) . . ?
C4 C3 C2 118.7(2) . . ?
C6 O1 Cu1 120.37(13) . . ?
C6 O2 Cu1 108.01(12) 5_665 . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 1002489'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_complex3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 Cl Cu N3 O'
_chemical_formula_weight         417.38

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   22.477(4)
_cell_length_b                   12.052(2)
_cell_length_c                   20.103(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.013(5)
_cell_angle_gamma                90.00
_cell_volume                     5326.5(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7833
_cell_measurement_theta_min      2.710
_cell_measurement_theta_max      33.638

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.041
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1720
_exptl_absorpt_coefficient_mu    0.930
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.7489
_exptl_absorpt_correction_T_max  0.8287
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15481
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         23.87
_reflns_number_total             4042
_reflns_number_gt                3022
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER AXS SMART 3'
_computing_cell_refinement       'BRUKER AXS SMART 3'
_computing_data_reduction        'BRUKER AXS SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'BRUKER SHELXLTL'
_computing_publication_material  'MERCURY 1.4'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0703P)²+82.9867P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4042
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1069
_refine_ls_R_factor_gt           0.0846
_refine_ls_wR_factor_ref         0.2326
_refine_ls_wR_factor_gt          0.2239
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.164
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.06912(4) 0.11855(8) -0.00372(5) 0.0319(3) Uani 1 1 d . . .
Cl1 Cl 0.00583(9) 0.03701(19) -0.09194(10) 0.0407(6) Uani 1 1 d . . .
N3 N 0.0160(3) 0.2536(6) -0.0098(4) 0.0371(17) Uani 1 1 d . . .
C9 C 0.0025(3) 0.2994(7) 0.0457(4) 0.035(2) Uani 1 1 d . . .
C13 C -0.0101(4) 0.2963(8) -0.0704(5) 0.045(2) Uani 1 1 d . . .
H13 H 0.0007 0.2666 -0.1089 0.054 Uiso 1 1 calc R . .
C10 C -0.0396(4) 0.3866(7) 0.0420(5) 0.044(2) Uani 1 1 d . . .
H10 H -0.0484 0.4170 0.0814 0.053 Uiso 1 1 calc R . .
C12 C -0.0513(4) 0.3803(8) -0.0790(5) 0.053(3) Uani 1 1 d . . .
H12 H -0.0685 0.4071 -0.1221 0.064 Uiso 1 1 calc R . .
C11 C -0.0671(4) 0.4254(8) -0.0202(6) 0.048(2) Uani 1 1 d . . .
H11 H -0.0961 0.4813 -0.0240 0.058 Uiso 1 1 calc R . .
N1 N 0.1199(3) -0.0185(5) 0.0189(3) 0.0307(16) Uani 1 1 d . . .
C4 C 0.1834(4) -0.1137(8) 0.1079(5) 0.045(2) Uani 1 1 d . . .
H4 H 0.2038 -0.1147 0.1532 0.053 Uiso 1 1 calc R . .
C1 C 0.1249(3) -0.1030(7) -0.0235(5) 0.038(2) Uani 1 1 d . . .
H1 H 0.1050 -0.0987 -0.0689 0.046 Uiso 1 1 calc R . .
C3 C 0.1880(4) -0.2018(8) 0.0664(6) 0.051(3) Uani 1 1 d . . .
H3 H 0.2103 -0.2644 0.0832 0.061 Uiso 1 1 calc R . .
C5 C 0.1487(3) -0.0243(7) 0.0825(4) 0.0309(19) Uani 1 1 d . . .
C2 C 0.1587(4) -0.1955(7) -0.0006(5) 0.045(2) Uani 1 1 d . . .
H2 H 0.1618 -0.2534 -0.0303 0.055 Uiso 1 1 calc R . .
C6 C 0.1401(4) 0.0758(7) 0.1261(4) 0.035(2) Uani 1 1 d . . .
H6A H 0.1059 0.0630 0.1477 0.042 Uiso 1 1 calc R . .
H6B H 0.1762 0.0865 0.1615 0.042 Uiso 1 1 calc R . .
N2 N 0.1285(2) 0.1783(5) 0.0819(3) 0.0242(14) Uani 1 1 d . . .
C14 C 0.1885(3) 0.2102(7) 0.0663(4) 0.0308(18) Uani 1 1 d . . .
H14A H 0.2043 0.1480 0.0446 0.037 Uiso 1 1 calc R . .
H14B H 0.2170 0.2257 0.1086 0.037 Uiso 1 1 calc R . .
C15 C 0.1844(3) 0.3105(6) 0.0204(4) 0.0310(19) Uani 1 1 d . . .
C19 C 0.1556(4) 0.3900(9) -0.0907(5) 0.046(2) Uani 1 1 d . . .
H19 H 0.1357 0.3841 -0.1360 0.055 Uiso 1 1 calc R . .
C20 C 0.1569(3) 0.3028(7) -0.0483(4) 0.033(2) Uani 1 1 d . . .
C16 C 0.2131(3) 0.4091(7) 0.0434(5) 0.035(2) Uani 1 1 d . . .
H16 H 0.2328 0.4158 0.0887 0.043 Uiso 1 1 calc R . .
C17 C 0.2126(4) 0.4975(8) -0.0004(6) 0.049(3) Uani 1 1 d . . .
H17 H 0.2318 0.5634 0.0159 0.059 Uiso 1 1 calc R . .
C18 C 0.1844(4) 0.4896(9) -0.0663(6) 0.052(3) Uani 1 1 d . . .
H18 H 0.1841 0.5497 -0.0954 0.062 Uiso 1 1 calc R . .
O1 O 0.1314(2) 0.2017(5) -0.0697(3) 0.0400(15) Uani 1 1 d . . .
C7 C 0.1041(4) 0.2646(7) 0.1203(4) 0.036(2) Uani 1 1 d . . .
H7A H 0.1144 0.3368 0.1047 0.043 Uiso 1 1 calc R . .
H7B H 0.1234 0.2581 0.1680 0.043 Uiso 1 1 calc R . .
C8 C 0.0361(4) 0.2580(7) 0.1135(4) 0.036(2) Uani 1 1 d . . .
H8A H 0.0246 0.1816 0.1193 0.044 Uiso 1 1 calc R . .
H8B H 0.0245 0.3018 0.1492 0.044 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 2.006(7) . ?
Cu1 N3 2.008(7) . ?
Cu1 N2 2.075(6) . ?
Cu1 Cl1 2.255(2) . ?
Cu1 O1 2.345(6) . ?
N3 C9 1.335(11) . ?
N3 C13 1.340(11) . ?
C9 C10 1.405(12) . ?
C9 C8 1.498(12) . ?
C13 C12 1.358(13) . ?
C13 H13 0.9300 . ?
C10 C11 1.358(13) . ?
C10 H10 0.9300 . ?
C12 C11 1.412(14) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
N1 C5 1.310(10) . ?
N1 C1 1.346(10) . ?
C4 C5 1.365(12) . ?
C4 C3 1.367(13) . ?
C4 H4 0.9300 . ?
C1 C2 1.374(12) . ?
C1 H1 0.9300 . ?
C3 C2 1.372(14) . ?
C3 H3 0.9300 . ?
C5 C6 1.528(11) . ?
C2 H2 0.9300 . ?
C6 N2 1.512(10) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
N2 C7 1.467(10) . ?
N2 C14 1.498(9) . ?
C14 C15 1.512(11) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.384(11) . ?
C15 C20 1.395(12) . ?
C19 C20 1.350(12) . ?
C19 C18 1.403(14) . ?
C19 H19 0.9300 . ?
C20 O1 1.377(10) . ?
C16 C17 1.381(13) . ?
C16 H16 0.9300 . ?
C17 C18 1.348(14) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C7 C8 1.507(11) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?

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 N3 170.1(3) . . ?
N1 Cu1 N2 82.0(2) . . ?
N3 Cu1 N2 92.3(3) . . ?
N1 Cu1 Cl1 93.17(19) . . ?
N3 Cu1 Cl1 92.0(2) . . ?
N2 Cu1 Cl1 174.37(19) . . ?
N1 Cu1 O1 95.8(2) . . ?
N3 Cu1 O1 92.1(2) . . ?
N2 Cu1 O1 88.0(2) . . ?
Cl1 Cu1 O1 95.42(15) . . ?
C9 N3 C13 118.0(7) . . ?
C9 N3 Cu1 121.3(6) . . ?
C13 N3 Cu1 120.6(6) . . ?
N3 C9 C10 122.1(8) . . ?
N3 C9 C8 117.6(7) . . ?
C10 C9 C8 120.3(8) . . ?
N3 C13 C12 124.0(9) . . ?
N3 C13 H13 118.0 . . ?
C12 C13 H13 118.0 . . ?
C11 C10 C9 118.6(9) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C13 C12 C11 117.6(9) . . ?
C13 C12 H12 121.2 . . ?
C11 C12 H12 121.2 . . ?
C10 C11 C12 119.5(9) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C5 N1 C1 119.2(7) . . ?
C5 N1 Cu1 114.0(5) . . ?
C1 N1 Cu1 126.7(6) . . ?
C5 C4 C3 119.6(9) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C1 C2 121.0(9) . . ?
N1 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C4 C3 C2 118.4(9) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
N1 C5 C4 122.4(8) . . ?
N1 C5 C6 115.0(7) . . ?
C4 C5 C6 122.7(8) . . ?
C3 C2 C1 119.5(9) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
N2 C6 C5 109.6(6) . . ?
N2 C6 H6A 109.7 . . ?
C5 C6 H6A 109.7 . . ?
N2 C6 H6B 109.7 . . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C7 N2 C14 112.4(6) . . ?
C7 N2 C6 107.9(6) . . ?
C14 N2 C6 106.2(5) . . ?
C7 N2 Cu1 115.9(4) . . ?
C14 N2 Cu1 111.5(4) . . ?
C6 N2 Cu1 101.9(4) . . ?
N2 C14 C15 112.9(6) . . ?
N2 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
N2 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C20 117.9(8) . . ?
C16 C15 C14 121.2(8) . . ?
C20 C15 C14 120.6(7) . . ?
C20 C19 C18 119.8(9) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 O1 122.6(8) . . ?
C19 C20 C15 121.4(8) . . ?
O1 C20 C15 116.0(7) . . ?
C17 C16 C15 120.6(9) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 120.8(9) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 119.5(9) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C20 O1 Cu1 117.4(5) . . ?
N2 C7 C8 113.4(7) . . ?
N2 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
N2 C7 H7B 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C7 112.1(7) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?

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
N1 Cu1 N3 C9 13.4(18) . . . . ?
N2 Cu1 N3 C9 -41.5(6) . . . . ?
Cl1 Cu1 N3 C9 135.0(6) . . . . ?
O1 Cu1 N3 C9 -129.5(6) . . . . ?
N1 Cu1 N3 C13 -162.4(13) . . . . ?
N2 Cu1 N3 C13 142.7(6) . . . . ?
Cl1 Cu1 N3 C13 -40.9(6) . . . . ?
O1 Cu1 N3 C13 54.6(6) . . . . ?
C13 N3 C9 C10 2.7(11) . . . . ?
Cu1 N3 C9 C10 -173.2(6) . . . . ?
C13 N3 C9 C8 -174.6(7) . . . . ?
Cu1 N3 C9 C8 9.5(9) . . . . ?
C9 N3 C13 C12 -2.9(13) . . . . ?
Cu1 N3 C13 C12 173.1(7) . . . . ?
N3 C9 C10 C11 -0.3(12) . . . . ?
C8 C9 C10 C11 177.0(8) . . . . ?
N3 C13 C12 C11 0.5(14) . . . . ?
C9 C10 C11 C12 -2.2(13) . . . . ?
C13 C12 C11 C10 2.1(13) . . . . ?
N3 Cu1 N1 C5 -33.3(17) . . . . ?
N2 Cu1 N1 C5 22.3(5) . . . . ?
Cl1 Cu1 N1 C5 -154.8(5) . . . . ?
O1 Cu1 N1 C5 109.5(5) . . . . ?
N3 Cu1 N1 C1 144.2(13) . . . . ?
N2 Cu1 N1 C1 -160.2(6) . . . . ?
Cl1 Cu1 N1 C1 22.7(6) . . . . ?
O1 Cu1 N1 C1 -73.1(6) . . . . ?
C5 N1 C1 C2 1.0(11) . . . . ?
Cu1 N1 C1 C2 -176.3(6) . . . . ?
C5 C4 C3 C2 2.0(13) . . . . ?
C1 N1 C5 C4 -0.5(11) . . . . ?
Cu1 N1 C5 C4 177.2(6) . . . . ?
C1 N1 C5 C6 180.0(6) . . . . ?
Cu1 N1 C5 C6 -2.3(8) . . . . ?
C3 C4 C5 N1 -1.0(12) . . . . ?
C3 C4 C5 C6 178.4(8) . . . . ?
C4 C3 C2 C1 -1.5(13) . . . . ?
N1 C1 C2 C3 0.0(12) . . . . ?
N1 C5 C6 N2 -28.7(9) . . . . ?
C4 C5 C6 N2 151.8(7) . . . . ?
C5 C6 N2 C7 164.7(6) . . . . ?
C5 C6 N2 C14 -74.6(7) . . . . ?
C5 C6 N2 Cu1 42.2(6) . . . . ?
N1 Cu1 N2 C7 -151.4(6) . . . . ?
N3 Cu1 N2 C7 20.4(6) . . . . ?
Cl1 Cu1 N2 C7 -120.2(16) . . . . ?
O1 Cu1 N2 C7 112.4(5) . . . . ?
N1 Cu1 N2 C14 78.4(5) . . . . ?
N3 Cu1 N2 C14 -109.8(5) . . . . ?
Cl1 Cu1 N2 C14 109.6(17) . . . . ?
O1 Cu1 N2 C14 -17.8(5) . . . . ?
N1 Cu1 N2 C6 -34.6(4) . . . . ?
N3 Cu1 N2 C6 137.2(4) . . . . ?
Cl1 Cu1 N2 C6 -3(2) . . . . ?
O1 Cu1 N2 C6 -130.7(4) . . . . ?
C7 N2 C14 C15 -63.8(8) . . . . ?
C6 N2 C14 C15 178.4(6) . . . . ?
Cu1 N2 C14 C15 68.2(7) . . . . ?
N2 C14 C15 C16 114.4(7) . . . . ?
N2 C14 C15 C20 -72.4(9) . . . . ?
C18 C19 C20 O1 -177.6(7) . . . . ?
C18 C19 C20 C15 2.5(12) . . . . ?
C16 C15 C20 C19 -3.0(11) . . . . ?
C14 C15 C20 C19 -176.5(7) . . . . ?
C16 C15 C20 O1 177.1(6) . . . . ?
C14 C15 C20 O1 3.5(10) . . . . ?
C20 C15 C16 C17 1.9(11) . . . . ?
C14 C15 C16 C17 175.4(7) . . . . ?
C15 C16 C17 C18 -0.3(12) . . . . ?
C16 C17 C18 C19 -0.3(12) . . . . ?
C20 C19 C18 C17 -0.8(13) . . . . ?
C19 C20 O1 Cu1 -132.5(7) . . . . ?
C15 C20 O1 Cu1 47.4(8) . . . . ?
N1 Cu1 O1 C20 -119.2(5) . . . . ?
N3 Cu1 O1 C20 54.8(5) . . . . ?
N2 Cu1 O1 C20 -37.5(5) . . . . ?
Cl1 Cu1 O1 C20 147.0(5) . . . . ?
C14 N2 C7 C8 157.4(7) . . . . ?
C6 N2 C7 C8 -85.8(8) . . . . ?
Cu1 N2 C7 C8 27.6(9) . . . . ?
N3 C9 C8 C7 54.5(10) . . . . ?
C10 C9 C8 C7 -122.9(8) . . . . ?
N2 C7 C8 C9 -75.1(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        23.87
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.129


_platon_squeeze_details          
;
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
  _platon_squeeze_void_nr
  _platon_squeeze_void_average_x
  _platon_squeeze_void_average_y
  _platon_squeeze_void_average_z
  _platon_squeeze_void_volume
  _platon_squeeze_void_count_electrons
  _platon_squeeze_void_content
   1  0.853 -0.024  0.250      1066       210 ' '
   2  0.842 -0.020  0.750      1065       210 ' '

;
_database_code_depnum_ccdc_archive 'CCDC 1002490'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_LigandL1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H16 N4'
_chemical_formula_sum            'C17 H16 N4'
_chemical_formula_weight         276.34

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   8.887(8)
_cell_length_b                   17.728(15)
_cell_length_c                   18.635(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.707(12)
_cell_angle_gamma                90.00
_cell_volume                     2936(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10933
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      25.9

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9862
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10933
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.85
_reflns_number_total             2813
_reflns_number_gt                1927
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER AXS SMART 3'
_computing_cell_refinement       'BRUKER AXS SMART 3'
_computing_data_reduction        'BRUKER AXS SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'BRUKER SHELXLTL'
_computing_publication_material  'MERCURY 1.4'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0812P)²+1.5466P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2813
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.1128
_refine_ls_goodness_of_fit_ref   0.833
_refine_ls_restrained_S_all      0.833
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H1' H 0.499(2) 0.4395(10) 0.5456(10) 0.057(5) Uiso 1 1 d . . .
H2' H 0.676(2) 0.3014(10) 0.5361(11) 0.060(6) Uiso 1 1 d . . .
N4 N 0.79100(15) 0.18743(8) 0.57723(8) 0.0500(4) Uani 1 1 d . . .
N1 N 0.68823(15) 0.53062(8) 0.52617(8) 0.0514(4) Uani 1 1 d . . .
C1 C 0.70041(18) 0.47241(9) 0.57113(9) 0.0474(4) Uani 1 1 d . . .
C7 C 0.40824(18) 0.33627(9) 0.62881(9) 0.0442(4) Uani 1 1 d . . .
C8 C 0.32311(19) 0.38120(10) 0.67353(10) 0.0528(5) Uani 1 1 d . . .
H8 H 0.3666 0.4236 0.6946 0.063 Uiso 1 1 calc R . .
C13 C 0.70932(17) 0.23530(9) 0.61693(9) 0.0432(4) Uani 1 1 d . . .
C14 C 0.6790(2) 0.22090(10) 0.68888(10) 0.0549(5) Uani 1 1 d . . .
H14 H 0.6206 0.2541 0.7153 0.066 Uiso 1 1 calc R . .
C17 C 0.8448(2) 0.12577(11) 0.60975(11) 0.0631(5) Uani 1 1 d . . .
H17 H 0.9015 0.0925 0.5826 0.076 Uiso 1 1 calc R . .
C9 C 0.1749(2) 0.36407(12) 0.68734(11) 0.0643(5) Uani 1 1 d . . .
H9 H 0.1192 0.3945 0.7178 0.077 Uiso 1 1 calc R . .
C12 C 0.3416(2) 0.27369(10) 0.59798(10) 0.0563(5) Uani 1 1 d . . .
H12 H 0.3972 0.2427 0.5680 0.068 Uiso 1 1 calc R . .
C5 C 0.8053(2) 0.57785(11) 0.52208(12) 0.0645(6) Uani 1 1 d . . .
H5 H 0.7978 0.6180 0.4901 0.077 Uiso 1 1 calc R . .
C15 C 0.7367(3) 0.15703(11) 0.72004(11) 0.0706(6) Uani 1 1 d . . .
H15 H 0.7182 0.1466 0.7680 0.085 Uiso 1 1 calc R . .
C10 C 0.1093(2) 0.30134(13) 0.65564(12) 0.0698(6) Uani 1 1 d . . .
H10 H 0.0091 0.2897 0.6644 0.084 Uiso 1 1 calc R . .
C11 C 0.1923(2) 0.25654(12) 0.61135(12) 0.0672(6) Uani 1 1 d . . .
H11 H 0.1483 0.2144 0.5901 0.081 Uiso 1 1 calc R . .
C4 C 0.9343(2) 0.57121(12) 0.56142(13) 0.0742(7) Uani 1 1 d . . .
H4 H 1.0120 0.6060 0.5573 0.089 Uiso 1 1 calc R . .
C2 C 0.8301(2) 0.46043(12) 0.61206(12) 0.0709(6) Uani 1 1 d . . .
H2 H 0.8383 0.4187 0.6420 0.085 Uiso 1 1 calc R . .
C3 C 0.9454(2) 0.51130(13) 0.60738(14) 0.0828(7) Uani 1 1 d . . .
H3 H 1.0316 0.5051 0.6356 0.099 Uiso 1 1 calc R . .
C16 C 0.8223(3) 0.10829(11) 0.67989(12) 0.0741(6) Uani 1 1 d . . .
H16 H 0.8634 0.0648 0.7001 0.089 Uiso 1 1 calc R . .
N2 N 0.57678(16) 0.42595(8) 0.57394(8) 0.0513(4) Uani 1 1 d . . .
N3 N 0.65985(16) 0.29867(8) 0.58210(9) 0.0514(4) Uani 1 1 d . . .
C6 C 0.57208(18) 0.35771(9) 0.61572(9) 0.0453(4) Uani 1 1 d . . .
H6 H 0.6188 0.3686 0.6625 0.054 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N4 C17 1.335(2) . ?
N4 C13 1.344(2) . ?
N1 C1 1.333(2) . ?
N1 C5 1.338(2) . ?
C1 N2 1.375(2) . ?
C1 C2 1.390(3) . ?
C7 C12 1.380(2) . ?
C7 C8 1.384(2) . ?
C7 C6 1.527(3) . ?
C8 C9 1.379(3) . ?
C8 H8 0.9300 . ?
C13 N3 1.367(2) . ?
C13 C14 1.394(3) . ?
C14 C15 1.369(3) . ?
C14 H14 0.9300 . ?
C17 C16 1.360(3) . ?
C17 H17 0.9300 . ?
C9 C10 1.385(3) . ?
C9 H9 0.9300 . ?
C12 C11 1.387(3) . ?
C12 H12 0.9300 . ?
C5 C4 1.358(3) . ?
C5 H5 0.9300 . ?
C15 C16 1.378(3) . ?
C15 H15 0.9300 . ?
C10 C11 1.368(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C4 C3 1.367(3) . ?
C4 H4 0.9300 . ?
C2 C3 1.368(3) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C16 H16 0.9300 . ?
N2 C6 1.439(2) . ?
N2 H1' 0.900(18) . ?
N3 C6 1.452(2) . ?
N3 H2' 0.87(2) . ?
C6 H6 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
C17 N4 C13 117.36(17) . . ?
C1 N1 C5 117.59(15) . . ?
N1 C1 N2 115.41(14) . . ?
N1 C1 C2 121.56(16) . . ?
N2 C1 C2 123.03(17) . . ?
C12 C7 C8 118.57(17) . . ?
C12 C7 C6 122.61(16) . . ?
C8 C7 C6 118.82(15) . . ?
C9 C8 C7 121.06(18) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
N4 C13 N3 115.47(16) . . ?
N4 C13 C14 121.70(16) . . ?
N3 C13 C14 122.82(16) . . ?
C15 C14 C13 118.91(19) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
N4 C17 C16 124.51(19) . . ?
N4 C17 H17 117.7 . . ?
C16 C17 H17 117.7 . . ?
C8 C9 C10 119.68(19) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C7 C12 C11 120.55(19) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
N1 C5 C4 124.51(19) . . ?
N1 C5 H5 117.7 . . ?
C4 C5 H5 117.7 . . ?
C14 C15 C16 119.6(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C11 C10 C9 119.78(19) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C5 C4 C3 117.32(18) . . ?
C5 C4 H4 121.3 . . ?
C3 C4 H4 121.3 . . ?
C3 C2 C1 118.73(19) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 120.25(18) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C17 C16 C15 117.86(19) . . ?
C17 C16 H16 121.1 . . ?
C15 C16 H16 121.1 . . ?
C1 N2 C6 123.55(14) . . ?
C1 N2 H1' 115.5(12) . . ?
C6 N2 H1' 120.9(12) . . ?
C13 N3 C6 123.98(16) . . ?
C13 N3 H2' 117.0(12) . . ?
C6 N3 H2' 118.8(12) . . ?
N2 C6 N3 110.68(15) . . ?
N2 C6 C7 109.25(13) . . ?
N3 C6 C7 114.07(14) . . ?
N2 C6 H6 107.5 . . ?
N3 C6 H6 107.5 . . ?
C7 C6 H6 107.5 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.85
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.032
_database_code_depnum_ccdc_archive 'CCDC 990722'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Complex1'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H38 Cl Cu N2 O4 P2'
_chemical_formula_weight         843.71

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   10.1166(10)
_cell_length_b                   14.9515(14)
_cell_length_c                   26.557(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.743(2)
_cell_angle_gamma                90.00
_cell_volume                     4015.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1740
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale green'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1744
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29280
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_sigmaI/netI    0.0437
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         24.99
_reflns_number_total             6423
_reflns_number_gt                5430
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1212P)²+1.3347P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6423
_refine_ls_number_parameters     507
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1911
_refine_ls_wR_factor_gt          0.1693
_refine_ls_goodness_of_fit_ref   1.207
_refine_ls_restrained_S_all      1.207
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.36787(4) 0.74125(3) 0.130284(15) 0.0174(9) Uani 1 1 d . . .
P2 P 0.56999(8) 0.68277(6) 0.12295(3) 0.0173(9) Uani 1 1 d . . .
P1 P 0.32137(8) 0.88844(6) 0.12724(3) 0.0179(9) Uani 1 1 d . . .
Cl1 Cl 0.05541(10) 0.28710(7) 0.15062(3) 0.0315(9) Uani 1 1 d . . .
O3 O 0.0339(3) 0.3256(2) 0.19918(11) 0.0436(11) Uani 1 1 d . . .
O2 O 0.0708(4) 0.3575(2) 0.11438(11) 0.0460(12) Uani 1 1 d . . .
O1 O -0.0584(4) 0.2339(2) 0.13623(15) 0.0583(13) Uani 1 1 d . . .
O4 O 0.1712(4) 0.2331(3) 0.15294(15) 0.0597(13) Uani 1 1 d . . .
C2 C 0.3181(4) 0.9356(2) 0.02546(14) 0.0288(12) Uani 1 1 d . . .
H2 H 0.4059 0.9522 0.0311 0.035 Uiso 1 1 calc R . .
C1 C 0.2432(4) 0.9090(2) 0.06591(13) 0.0230(11) Uani 1 1 d . . .
C6 C 0.1112(4) 0.8834(3) 0.05658(16) 0.0315(12) Uani 1 1 d . . .
H6 H 0.0595 0.8649 0.0830 0.038 Uiso 1 1 calc R . .
C3 C 0.2641(5) 0.9379(3) -0.02295(16) 0.0447(14) Uani 1 1 d . . .
H3 H 0.3151 0.9568 -0.0495 0.054 Uiso 1 1 calc R . .
C4 C 0.1339(6) 0.9121(3) -0.03186(18) 0.0496(15) Uani 1 1 d . . .
H4 H 0.0979 0.9125 -0.0645 0.059 Uiso 1 1 calc R . .
C5 C 0.0581(5) 0.8860(3) 0.00752(19) 0.0448(15) Uani 1 1 d . . .
H5 H -0.0297 0.8698 0.0014 0.054 Uiso 1 1 calc R . .
C7 C 0.4513(3) 0.9732(2) 0.13315(12) 0.0199(11) Uani 1 1 d . . .
C12 C 0.4282(4) 1.0627(2) 0.12016(14) 0.0264(11) Uani 1 1 d . . .
H12 H 0.3465 1.0794 0.1062 0.032 Uiso 1 1 calc R . .
C11 C 0.5254(4) 1.1264(3) 0.12792(16) 0.0318(12) Uani 1 1 d . . .
H11 H 0.5092 1.1857 0.1192 0.038 Uiso 1 1 calc R . .
C10 C 0.6469(4) 1.1019(3) 0.14875(16) 0.0343(12) Uani 1 1 d . . .
H10 H 0.7129 1.1447 0.1536 0.041 Uiso 1 1 calc R . .
C9 C 0.6704(4) 1.0142(3) 0.16233(16) 0.0341(12) Uani 1 1 d . . .
H9 H 0.7519 0.9980 0.1768 0.041 Uiso 1 1 calc R . .
C8 C 0.5728(4) 0.9500(3) 0.15451(14) 0.0259(11) Uani 1 1 d . . .
H8 H 0.5893 0.8910 0.1637 0.031 Uiso 1 1 calc R . .
C13 C 0.2059(3) 0.9314(2) 0.17302(13) 0.0201(11) Uani 1 1 d . . .
C15 C 0.1441(4) 0.9319(3) 0.26026(15) 0.0321(12) Uani 1 1 d . . .
H15 H 0.1551 0.9105 0.2930 0.039 Uiso 1 1 calc R . .
C14 C 0.2220(4) 0.8994(2) 0.22200(14) 0.0248(11) Uani 1 1 d . . .
H14 H 0.2855 0.8559 0.2293 0.030 Uiso 1 1 calc R . .
C16 C 0.0501(4) 0.9966(3) 0.24883(16) 0.0365(13) Uani 1 1 d . . .
H16 H -0.0041 1.0177 0.2739 0.044 Uiso 1 1 calc R . .
C17 C 0.0363(4) 1.0303(3) 0.20026(17) 0.0318(12) Uani 1 1 d . . .
H17 H -0.0256 1.0748 0.1931 0.038 Uiso 1 1 calc R . .
C18 C 0.6343(3) 0.7052(2) 0.06073(13) 0.0202(11) Uani 1 1 d . . .
C23 C 0.6807(4) 0.6390(3) 0.02923(14) 0.0257(11) Uani 1 1 d . . .
H23 H 0.6820 0.5797 0.0399 0.031 Uiso 1 1 calc R . .
C21 C 0.7244(5) 0.7490(3) -0.03408(16) 0.0342(13) Uani 1 1 d . . .
H21 H 0.7551 0.7638 -0.0657 0.041 Uiso 1 1 calc R . .
C22 C 0.7252(4) 0.6611(3) -0.01832(14) 0.0318(12) Uani 1 1 d . . .
H22 H 0.7556 0.6164 -0.0395 0.038 Uiso 1 1 calc R . .
C20 C 0.6782(5) 0.8147(3) -0.00297(16) 0.0370(13) Uani 1 1 d . . .
H20 H 0.6770 0.8739 -0.0138 0.044 Uiso 1 1 calc R . .
C19 C 0.6337(4) 0.7935(3) 0.04416(15) 0.0291(12) Uani 1 1 d . . .
H19 H 0.6031 0.8386 0.0650 0.035 Uiso 1 1 calc R . .
C24 C 0.6962(3) 0.7256(2) 0.16672(13) 0.0191(11) Uani 1 1 d . . .
C25 C 0.8246(4) 0.7486(2) 0.15361(15) 0.0235(11) Uani 1 1 d . . .
H25 H 0.8496 0.7440 0.1203 0.028 Uiso 1 1 calc R . .
C29 C 0.6601(4) 0.7330(2) 0.21668(14) 0.0222(11) Uani 1 1 d . . .
H29 H 0.5747 0.7182 0.2257 0.027 Uiso 1 1 calc R . .
C26 C 0.9138(4) 0.7781(3) 0.18984(16) 0.0295(12) Uani 1 1 d . . .
H26 H 0.9989 0.7939 0.1809 0.035 Uiso 1 1 calc R . .
C28 C 0.7512(4) 0.7624(3) 0.25292(16) 0.0283(12) Uani 1 1 d . . .
H28 H 0.7271 0.7673 0.2863 0.034 Uiso 1 1 calc R . .
C27 C 0.8779(4) 0.7843(3) 0.23955(15) 0.0303(12) Uani 1 1 d . . .
H27 H 0.9393 0.8033 0.2640 0.036 Uiso 1 1 calc R . .
C30 C 0.5924(3) 0.5616(2) 0.12871(13) 0.0204(11) Uani 1 1 d . . .
C33 C 0.6308(4) 0.3772(3) 0.13238(16) 0.0340(12) Uani 1 1 d . . .
H33 H 0.6439 0.3156 0.1333 0.041 Uiso 1 1 calc R . .
C31 C 0.7114(4) 0.5257(2) 0.14735(15) 0.0261(11) Uani 1 1 d . . .
H31 H 0.7789 0.5635 0.1588 0.031 Uiso 1 1 calc R . .
C32 C 0.7293(4) 0.4337(3) 0.14891(16) 0.0313(12) Uani 1 1 d . . .
H32 H 0.8090 0.4103 0.1613 0.038 Uiso 1 1 calc R . .
C34 C 0.5110(4) 0.4121(3) 0.11422(16) 0.0355(13) Uani 1 1 d . . .
H34 H 0.4437 0.3739 0.1031 0.043 Uiso 1 1 calc R . .
C35 C 0.4919(4) 0.5042(3) 0.11271(14) 0.0282(12) Uani 1 1 d . . .
H35 H 0.4114 0.5274 0.1009 0.034 Uiso 1 1 calc R . .
C36 C 0.1136(4) 0.9980(2) 0.16291(15) 0.0266(11) Uani 1 1 d . . .
H36 H 0.1041 1.0210 0.1305 0.032 Uiso 1 1 calc R . .
N1 N 0.2378(3) 0.66958(19) 0.17228(11) 0.0205(10) Uani 1 1 d . . .
N2 N 0.2550(3) 0.68065(19) 0.07250(11) 0.0225(10) Uani 1 1 d . . .
C41 C 0.1522(3) 0.6184(2) 0.14449(15) 0.0243(11) Uani 1 1 d . . .
C46 C 0.2632(4) 0.6950(3) 0.02335(14) 0.0296(12) Uani 1 1 d . . .
H46 H 0.3341 0.7280 0.0118 0.036 Uiso 1 1 calc R . .
C42 C 0.1537(4) 0.6309(2) 0.08957(15) 0.0260(11) Uani 1 1 d . . .
C37 C 0.2360(4) 0.6645(3) 0.22248(14) 0.0258(11) Uani 1 1 d . . .
H37 H 0.2954 0.6990 0.2415 0.031 Uiso 1 1 calc R . .
C45 C 0.1696(5) 0.6625(3) -0.01153(15) 0.0387(13) Uani 1 1 d . . .
H45 H 0.1772 0.6738 -0.0458 0.046 Uiso 1 1 calc R . .
C40 C 0.0684(4) 0.5586(3) 0.16807(18) 0.0337(12) Uani 1 1 d . . .
H40 H 0.0142 0.5209 0.1487 0.040 Uiso 1 1 calc R . .
C38 C 0.1484(4) 0.6093(3) 0.24717(16) 0.0344(13) Uani 1 1 d . . .
H38 H 0.1461 0.6093 0.2822 0.041 Uiso 1 1 calc R . .
C39 C 0.0652(4) 0.5549(3) 0.21921(18) 0.0380(13) Uani 1 1 d . . .
H39 H 0.0077 0.5161 0.2350 0.046 Uiso 1 1 calc R . .
C43 C 0.0586(4) 0.5974(3) 0.05624(18) 0.0440(14) Uani 1 1 d . . .
H43 H -0.0111 0.5636 0.0681 0.053 Uiso 1 1 calc R . .
C44 C 0.0672(5) 0.6140(4) 0.00555(19) 0.0506(16) Uani 1 1 d . . .
H44 H 0.0030 0.5920 -0.0170 0.061 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 2.052(3) . ?
Cu1 N2 2.091(3) . ?
Cu1 P2 2.2378(9) . ?
Cu1 P1 2.2513(10) . ?
P2 C24 1.817(3) . ?
P2 C18 1.825(4) . ?
P2 C30 1.832(4) . ?
P1 C1 1.815(4) . ?
P1 C13 1.828(3) . ?
P1 C7 1.830(3) . ?
Cl1 O4 1.422(4) . ?
Cl1 O3 1.435(3) . ?
Cl1 O2 1.438(3) . ?
Cl1 O1 1.442(4) . ?
C2 C3 1.382(6) . ?
C2 C1 1.392(6) . ?
C2 H2 0.9300 . ?
C1 C6 1.403(6) . ?
C6 C5 1.395(6) . ?
C6 H6 0.9300 . ?
C3 C4 1.387(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(8) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C7 C8 1.382(5) . ?
C7 C12 1.399(5) . ?
C12 C11 1.380(6) . ?
C12 H12 0.9300 . ?
C11 C10 1.382(6) . ?
C11 H11 0.9300 . ?
C10 C9 1.379(6) . ?
C10 H10 0.9300 . ?
C9 C8 1.388(6) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C13 C36 1.386(5) . ?
C13 C14 1.391(5) . ?
C15 C16 1.384(6) . ?
C15 C14 1.392(5) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C16 C17 1.388(6) . ?
C16 H16 0.9300 . ?
C17 C36 1.370(6) . ?
C17 H17 0.9300 . ?
C18 C23 1.387(5) . ?
C18 C19 1.392(6) . ?
C23 C22 1.393(5) . ?
C23 H23 0.9300 . ?
C21 C20 1.375(6) . ?
C21 C22 1.380(6) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C20 C19 1.380(6) . ?
C20 H20 0.9300 . ?
C19 H19 0.9300 . ?
C24 C29 1.391(5) . ?
C24 C25 1.398(5) . ?
C25 C26 1.371(6) . ?
C25 H25 0.9300 . ?
C29 C28 1.384(6) . ?
C29 H29 0.9300 . ?
C26 C27 1.383(6) . ?
C26 H26 0.9300 . ?
C28 C27 1.379(6) . ?
C28 H28 0.9300 . ?
C27 H27 0.9300 . ?
C30 C35 1.387(5) . ?
C30 C31 1.395(5) . ?
C33 C32 1.369(6) . ?
C33 C34 1.393(6) . ?
C33 H33 0.9300 . ?
C31 C32 1.387(6) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C34 C35 1.391(6) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
N1 C37 1.336(5) . ?
N1 C41 1.357(5) . ?
N2 C46 1.328(5) . ?
N2 C42 1.355(5) . ?
C41 C40 1.395(6) . ?
C41 C42 1.471(6) . ?
C46 C45 1.392(6) . ?
C46 H46 0.9300 . ?
C42 C43 1.381(6) . ?
C37 C38 1.390(6) . ?
C37 H37 0.9300 . ?
C45 C44 1.354(8) . ?
C45 H45 0.9300 . ?
C40 C39 1.361(7) . ?
C40 H40 0.9300 . ?
C38 C39 1.372(7) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C43 C44 1.374(7) . ?
C43 H43 0.9300 . ?
C44 H44 0.9300 . ?

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 80.09(12) . . ?
N1 Cu1 P2 116.47(8) . . ?
N2 Cu1 P2 104.29(9) . . ?
N1 Cu1 P1 113.15(8) . . ?
N2 Cu1 P1 106.76(8) . . ?
P2 Cu1 P1 124.70(4) . . ?
C24 P2 C18 104.57(16) . . ?
C24 P2 C30 102.26(16) . . ?
C18 P2 C30 102.19(16) . . ?
C24 P2 Cu1 115.64(12) . . ?
C18 P2 Cu1 111.01(11) . . ?
C30 P2 Cu1 119.35(12) . . ?
C1 P1 C13 105.52(16) . . ?
C1 P1 C7 104.61(16) . . ?
C13 P1 C7 99.91(15) . . ?
C1 P1 Cu1 106.40(11) . . ?
C13 P1 Cu1 117.15(12) . . ?
C7 P1 Cu1 121.69(12) . . ?
O4 Cl1 O3 109.6(2) . . ?
O4 Cl1 O2 109.8(2) . . ?
O3 Cl1 O2 109.3(2) . . ?
O4 Cl1 O1 110.4(3) . . ?
O3 Cl1 O1 108.5(2) . . ?
O2 Cl1 O1 109.2(2) . . ?
C3 C2 C1 121.1(4) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C1 C6 118.6(3) . . ?
C2 C1 P1 120.6(3) . . ?
C6 C1 P1 119.9(3) . . ?
C5 C6 C1 119.7(4) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C2 C3 C4 119.9(5) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.7(4) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C8 C7 C12 118.7(3) . . ?
C8 C7 P1 119.3(3) . . ?
C12 C7 P1 121.8(3) . . ?
C11 C12 C7 120.7(4) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
C12 C11 C10 119.9(4) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C9 C10 C11 120.0(4) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C9 C8 120.1(4) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C7 C8 C9 120.5(4) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C36 C13 C14 119.2(3) . . ?
C36 C13 P1 124.3(3) . . ?
C14 C13 P1 116.2(3) . . ?
C16 C15 C14 119.0(4) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C13 C14 C15 120.6(4) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C15 C16 C17 120.4(4) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C36 C17 C16 120.1(4) . . ?
C36 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C23 C18 C19 119.0(3) . . ?
C23 C18 P2 123.4(3) . . ?
C19 C18 P2 117.6(3) . . ?
C18 C23 C22 120.1(4) . . ?
C18 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C20 C21 C22 119.8(4) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C23 120.1(4) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C21 C20 C19 120.5(4) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C19 C18 120.4(4) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C29 C24 C25 119.4(3) . . ?
C29 C24 P2 116.0(3) . . ?
C25 C24 P2 124.6(3) . . ?
C26 C25 C24 120.0(4) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C28 C29 C24 120.0(3) . . ?
C28 C29 H29 120.0 . . ?
C24 C29 H29 120.0 . . ?
C25 C26 C27 120.3(4) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C27 C28 C29 120.1(4) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C27 C26 120.2(4) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C35 C30 C31 119.2(3) . . ?
C35 C30 P2 119.9(3) . . ?
C31 C30 P2 120.9(3) . . ?
C32 C33 C34 119.8(4) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
C32 C31 C30 120.1(4) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C33 C32 C31 120.6(4) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C35 C34 C33 120.0(4) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C30 C35 C34 120.2(4) . . ?
C30 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C17 C36 C13 120.6(4) . . ?
C17 C36 H36 119.7 . . ?
C13 C36 H36 119.7 . . ?
C37 N1 C41 118.9(3) . . ?
C37 N1 Cu1 126.9(3) . . ?
C41 N1 Cu1 114.1(2) . . ?
C46 N2 C42 119.2(3) . . ?
C46 N2 Cu1 127.0(3) . . ?
C42 N2 Cu1 113.2(2) . . ?
N1 C41 C40 120.3(4) . . ?
N1 C41 C42 116.2(3) . . ?
C40 C41 C42 123.5(4) . . ?
N2 C46 C45 122.4(4) . . ?
N2 C46 H46 118.8 . . ?
C45 C46 H46 118.8 . . ?
N2 C42 C43 120.2(4) . . ?
N2 C42 C41 115.6(3) . . ?
C43 C42 C41 124.1(4) . . ?
N1 C37 C38 122.2(4) . . ?
N1 C37 H37 118.9 . . ?
C38 C37 H37 118.9 . . ?
C44 C45 C46 118.4(4) . . ?
C44 C45 H45 120.8 . . ?
C46 C45 H45 120.8 . . ?
C39 C40 C41 120.5(4) . . ?
C39 C40 H40 119.8 . . ?
C41 C40 H40 119.8 . . ?
C39 C38 C37 119.1(4) . . ?
C39 C38 H38 120.5 . . ?
C37 C38 H38 120.5 . . ?
C40 C39 C38 118.9(4) . . ?
C40 C39 H39 120.5 . . ?
C38 C39 H39 120.5 . . ?
C44 C43 C42 119.9(4) . . ?
C44 C43 H43 120.0 . . ?
C42 C43 H43 120.0 . . ?
C45 C44 C43 119.8(4) . . ?
C45 C44 H44 120.1 . . ?
C43 C44 H44 120.1 . . ?

_diffrn_measured_fraction_theta_max 0.910
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.910
_refine_diff_density_max         1.009
_refine_diff_density_min         -0.769
_refine_diff_density_rms         0.173
_database_code_depnum_ccdc_archive 'CCDC 981596'
