# 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_bb
_database_code_depnum_ccdc_archive 'CCDC 1013683'
_audit_update_record             
;
2014-07-12 deposited with the CCDC.
2015-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 Cl2 Cu N3 O4'
_chemical_formula_weight         537.87

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   13.966(4)
_cell_length_b                   13.887(4)
_cell_length_c                   23.249(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4509(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4048
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      27.9

_exptl_crystal_description       Prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2200
_exptl_absorpt_coefficient_mu    1.242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7489
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33352
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3976
_reflns_number_gt                3733
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0535P)²+2.5948P] 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         3976
_refine_ls_number_parameters     382
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1007
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_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 0.08873(2) 0.41543(2) 0.004351(11) 0.01877(12) Uani 1 1 d . . .
N1 N 0.07853(13) 0.40397(15) 0.08907(8) 0.0198(4) Uani 1 1 d . . .
N2 N 0.08264(14) 0.26855(16) 0.00698(8) 0.0224(5) Uani 1 1 d . . .
N3 N 0.09615(13) 0.39166(16) -0.07975(9) 0.0221(4) Uani 1 1 d . . .
C1 C 0.10089(17) 0.4711(2) 0.12862(11) 0.0243(5) Uani 1 1 d . . .
C2 C 0.09091(18) 0.4552(2) 0.18660(11) 0.0293(6) Uani 1 1 d . . .
C3 C 0.0561(2) 0.3676(2) 0.20475(11) 0.0315(6) Uani 1 1 d . . .
C4 C 0.0333(2) 0.2973(2) 0.16467(11) 0.0309(6) Uani 1 1 d . . .
C5 C 0.04661(17) 0.31754(18) 0.10679(10) 0.0234(5) Uani 1 1 d . . .
C6 C 0.02620(19) 0.24538(19) 0.05963(10) 0.0251(5) Uani 1 1 d . . .
C7 C 0.03309(19) 0.2393(2) -0.04684(10) 0.0252(5) Uani 1 1 d . . .
C8 C 0.06596(17) 0.30322(18) -0.09513(10) 0.0239(5) Uani 1 1 d . . .
C9 C 0.0621(2) 0.2755(2) -0.15232(11) 0.0326(6) Uani 1 1 d . . .
C10 C 0.08951(19) 0.3412(2) -0.19427(12) 0.0363(7) Uani 1 1 d . . .
C11 C 0.1219(2) 0.4306(2) -0.17812(11) 0.0331(6) Uani 1 1 d . . .
C12 C 0.12470(18) 0.4540(2) -0.12058(11) 0.0272(6) Uani 1 1 d . . .
C13 C 0.1828(2) 0.2268(2) 0.00716(11) 0.0283(6) Uani 1 1 d . . .
C14 C 0.25025(17) 0.28329(19) 0.04555(11) 0.0284(6) Uani 1 1 d . . .
C15 C 0.29291(17) 0.36387(19) 0.02247(11) 0.0264(5) Uani 1 1 d . . .
C16 C 0.3468(2) 0.4276(2) 0.05680(15) 0.0398(7) Uani 1 1 d . . .
C17 C 0.3570(2) 0.4096(2) 0.11530(14) 0.0390(7) Uani 1 1 d . . .
C18 C 0.31783(18) 0.3262(2) 0.13862(12) 0.0340(6) Uani 1 1 d . . .
C19 C 0.26560(18) 0.2597(2) 0.10425(11) 0.0318(6) Uani 1 1 d . . .
C20 C 0.2321(2) 0.1720(2) 0.12964(12) 0.0357(7) Uani 1 1 d . . .
C21 C 0.2490(2) 0.1543(3) 0.18635(13) 0.0463(8) Uani 1 1 d . . .
C22 C 0.2970(2) 0.2196(3) 0.22158(14) 0.0548(10) Uani 1 1 d . . .
C23 C 0.3300(2) 0.3030(3) 0.19898(13) 0.0480(8) Uani 1 1 d . . .
Cl1 Cl 0.11293(5) 0.57571(4) 0.00152(2) 0.02214(16) Uani 1 1 d . . .
Cl2 Cl 0.39626(5) 0.03783(5) 0.35749(3) 0.03628(19) Uani 1 1 d . . .
H1 H 0.1191(18) 0.5235(19) 0.1157(11) 0.017(7) Uiso 1 1 d . . .
H2 H 0.1036(19) 0.502(2) 0.2113(13) 0.032(8) Uiso 1 1 d . . .
H3 H 0.050(2) 0.359(2) 0.2437(13) 0.038(8) Uiso 1 1 d . . .
H4 H 0.0137(19) 0.232(2) 0.1766(12) 0.034(8) Uiso 1 1 d . . .
H9 H 0.045(2) 0.214(2) -0.1596(12) 0.038(8) Uiso 1 1 d . . .
H10 H 0.085(2) 0.325(2) -0.2314(14) 0.049(10) Uiso 1 1 d . . .
H11 H 0.145(2) 0.474(2) -0.2038(13) 0.042(8) Uiso 1 1 d . . .
H12 H 0.1456(17) 0.5107(18) -0.1094(10) 0.013(6) Uiso 1 1 d . . .
H15 H 0.2851(19) 0.3815(19) -0.0169(11) 0.024(7) Uiso 1 1 d . . .
H16 H 0.375(2) 0.477(2) 0.0360(14) 0.045(9) Uiso 1 1 d . . .
H17 H 0.3946(17) 0.4482(19) 0.1371(11) 0.016(6) Uiso 1 1 d . . .
H20 H 0.197(2) 0.130(2) 0.1094(12) 0.036(8) Uiso 1 1 d . . .
H21 H 0.224(3) 0.092(3) 0.2049(15) 0.068(11) Uiso 1 1 d . . .
H22 H 0.307(3) 0.213(3) 0.2648(15) 0.063(10) Uiso 1 1 d . . .
H23 H 0.372(2) 0.356(3) 0.2242(14) 0.060(10) Uiso 1 1 d . . .
H6A H -0.0422(19) 0.2484(19) 0.0494(10) 0.020(6) Uiso 1 1 d . . .
H7A H -0.0325(18) 0.2471(18) -0.0402(9) 0.014(6) Uiso 1 1 d . . .
H13A H 0.2038(19) 0.2302(19) -0.0318(12) 0.029(7) Uiso 1 1 d . . .
H6B H 0.0388(18) 0.1789(19) 0.0735(10) 0.023(7) Uiso 1 1 d . . .
H7B H 0.045(2) 0.170(2) -0.0547(12) 0.037(8) Uiso 1 1 d . . .
H13B H 0.1700(18) 0.1652(19) 0.0196(11) 0.020(6) Uiso 1 1 d . . .
O2 O 0.34094(19) -0.0325(2) 0.32786(12) 0.0723(8) Uani 1 1 d . . .
O3 O 0.4248(2) 0.00321(19) 0.41339(11) 0.0668(8) Uani 1 1 d . . .
O4 O 0.34160(16) 0.12404(16) 0.36587(9) 0.0506(6) Uani 1 1 d . . .
O5 O 0.48037(15) 0.05931(17) 0.32389(10) 0.0515(6) Uani 1 1 d . . .


_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 1.981(2) . ?
Cu1 N3 1.986(2) . ?
Cu1 N2 2.042(2) . ?
Cu1 Cl1 2.2522(9) . ?
N1 C5 1.345(3) . ?
N1 C1 1.346(3) . ?
N2 C7 1.486(3) . ?
N2 C6 1.491(3) . ?
N2 C13 1.514(3) . ?
N3 C12 1.345(3) . ?
N3 C8 1.347(3) . ?
C1 C2 1.373(4) . ?
C1 H1 0.83(3) . ?
C2 C3 1.376(4) . ?
C2 H2 0.89(3) . ?
C3 C4 1.387(4) . ?
C3 H3 0.92(3) . ?
C4 C5 1.387(3) . ?
C4 H4 0.99(3) . ?
C5 C6 1.512(3) . ?
C6 H6A 0.99(3) . ?
C6 H6B 0.99(3) . ?
C7 C8 1.503(4) . ?
C7 H7A 0.94(2) . ?
C7 H7B 1.00(3) . ?
C8 C9 1.385(3) . ?
C9 C10 1.390(4) . ?
C9 H9 0.91(3) . ?
C10 C11 1.373(4) . ?
C10 H10 0.89(3) . ?
C11 C12 1.377(4) . ?
C11 H11 0.90(3) . ?
C12 H12 0.88(2) . ?
C13 C14 1.517(4) . ?
C13 H13A 0.95(3) . ?
C13 H13B 0.92(3) . ?
C14 C15 1.377(4) . ?
C14 C19 1.420(4) . ?
C15 C16 1.409(4) . ?
C15 H15 0.95(3) . ?
C16 C17 1.390(5) . ?
C16 H16 0.93(3) . ?
C17 C18 1.391(4) . ?
C17 H17 0.90(3) . ?
C18 C19 1.422(4) . ?
C18 C23 1.450(4) . ?
C19 C20 1.433(4) . ?
C20 C21 1.362(4) . ?
C20 H20 0.90(3) . ?
C21 C22 1.393(5) . ?
C21 H21 1.03(4) . ?
C22 C23 1.353(5) . ?
C22 H22 1.02(3) . ?
C23 H23 1.11(3) . ?
Cl2 O2 1.423(2) . ?
Cl2 O4 1.433(2) . ?
Cl2 O5 1.442(2) . ?
Cl2 O3 1.442(2) . ?

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 165.78(9) . . ?
N1 Cu1 N2 83.51(8) . . ?
N3 Cu1 N2 82.27(8) . . ?
N1 Cu1 Cl1 96.85(6) . . ?
N3 Cu1 Cl1 97.34(7) . . ?
N2 Cu1 Cl1 173.76(6) . . ?
C5 N1 C1 119.0(2) . . ?
C5 N1 Cu1 113.59(16) . . ?
C1 N1 Cu1 127.37(18) . . ?
C7 N2 C6 112.7(2) . . ?
C7 N2 C13 109.12(19) . . ?
C6 N2 C13 113.8(2) . . ?
C7 N2 Cu1 105.49(15) . . ?
C6 N2 Cu1 105.20(15) . . ?
C13 N2 Cu1 110.14(16) . . ?
C12 N3 C8 119.5(2) . . ?
C12 N3 Cu1 127.13(18) . . ?
C8 N3 Cu1 113.38(16) . . ?
N1 C1 C2 122.4(3) . . ?
N1 C1 H1 115.6(18) . . ?
C2 C1 H1 121.9(18) . . ?
C1 C2 C3 118.6(3) . . ?
C1 C2 H2 120(2) . . ?
C3 C2 H2 121.6(19) . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 117.1(19) . . ?
C4 C3 H3 123.0(19) . . ?
C3 C4 C5 118.6(3) . . ?
C3 C4 H4 121.5(16) . . ?
C5 C4 H4 119.7(16) . . ?
N1 C5 C4 121.5(2) . . ?
N1 C5 C6 115.6(2) . . ?
C4 C5 C6 122.9(2) . . ?
N2 C6 C5 110.6(2) . . ?
N2 C6 H6A 107.8(14) . . ?
C5 C6 H6A 109.2(14) . . ?
N2 C6 H6B 111.9(15) . . ?
C5 C6 H6B 110.3(14) . . ?
H6A C6 H6B 107(2) . . ?
N2 C7 C8 109.0(2) . . ?
N2 C7 H7A 106.6(14) . . ?
C8 C7 H7A 110.7(15) . . ?
N2 C7 H7B 110.0(16) . . ?
C8 C7 H7B 112.6(16) . . ?
H7A C7 H7B 108(2) . . ?
N3 C8 C9 121.4(2) . . ?
N3 C8 C7 115.8(2) . . ?
C9 C8 C7 122.7(2) . . ?
C8 C9 C10 118.7(3) . . ?
C8 C9 H9 116.9(18) . . ?
C10 C9 H9 124.3(18) . . ?
C11 C10 C9 119.5(3) . . ?
C11 C10 H10 121(2) . . ?
C9 C10 H10 120(2) . . ?
C10 C11 C12 119.2(3) . . ?
C10 C11 H11 122(2) . . ?
C12 C11 H11 118(2) . . ?
N3 C12 C11 121.7(3) . . ?
N3 C12 H12 117.8(16) . . ?
C11 C12 H12 120.5(16) . . ?
N2 C13 C14 112.2(2) . . ?
N2 C13 H13A 105.2(16) . . ?
C14 C13 H13A 110.0(16) . . ?
N2 C13 H13B 100.2(16) . . ?
C14 C13 H13B 114.7(16) . . ?
H13A C13 H13B 114(2) . . ?
C15 C14 C19 119.8(2) . . ?
C15 C14 C13 117.4(2) . . ?
C19 C14 C13 122.7(2) . . ?
C14 C15 C16 121.4(3) . . ?
C14 C15 H15 122.3(16) . . ?
C16 C15 H15 116.3(16) . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 H16 127(2) . . ?
C15 C16 H16 113(2) . . ?
C16 C17 C18 119.4(3) . . ?
C16 C17 H17 120.0(16) . . ?
C18 C17 H17 120.2(17) . . ?
C17 C18 C19 121.5(3) . . ?
C17 C18 C23 121.1(3) . . ?
C19 C18 C23 117.3(3) . . ?
C14 C19 C18 117.9(3) . . ?
C14 C19 C20 122.9(3) . . ?
C18 C19 C20 119.2(3) . . ?
C21 C20 C19 119.7(3) . . ?
C21 C20 H20 119.0(19) . . ?
C19 C20 H20 121.1(19) . . ?
C20 C21 C22 122.4(3) . . ?
C20 C21 H21 120(2) . . ?
C22 C21 H21 118(2) . . ?
C23 C22 C21 119.5(3) . . ?
C23 C22 H22 115(2) . . ?
C21 C22 H22 126(2) . . ?
C22 C23 C18 121.8(3) . . ?
C22 C23 H23 123.0(18) . . ?
C18 C23 H23 115.1(18) . . ?
O2 Cl2 O4 110.47(16) . . ?
O2 Cl2 O5 108.79(15) . . ?
O4 Cl2 O5 109.56(14) . . ?
O2 Cl2 O3 110.97(18) . . ?
O4 Cl2 O3 107.65(15) . . ?
O5 Cl2 O3 109.39(15) . . ?

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
N3 Cu1 N1 C5 -15.2(4) . . . . ?
N2 Cu1 N1 C5 -17.40(16) . . . . ?
Cl1 Cu1 N1 C5 168.88(15) . . . . ?
N3 Cu1 N1 C1 163.8(3) . . . . ?
N2 Cu1 N1 C1 161.6(2) . . . . ?
Cl1 Cu1 N1 C1 -12.1(2) . . . . ?
N1 Cu1 N2 C7 147.96(16) . . . . ?
N3 Cu1 N2 C7 -31.51(15) . . . . ?
Cl1 Cu1 N2 C7 -118.4(5) . . . . ?
N1 Cu1 N2 C6 28.59(15) . . . . ?
N3 Cu1 N2 C6 -150.87(15) . . . . ?
Cl1 Cu1 N2 C6 122.3(5) . . . . ?
N1 Cu1 N2 C13 -94.42(15) . . . . ?
N3 Cu1 N2 C13 86.12(15) . . . . ?
Cl1 Cu1 N2 C13 -0.7(6) . . . . ?
N1 Cu1 N3 C12 -165.6(3) . . . . ?
N2 Cu1 N3 C12 -163.4(2) . . . . ?
Cl1 Cu1 N3 C12 10.3(2) . . . . ?
N1 Cu1 N3 C8 16.4(4) . . . . ?
N2 Cu1 N3 C8 18.53(16) . . . . ?
Cl1 Cu1 N3 C8 -167.75(15) . . . . ?
C5 N1 C1 C2 -1.1(4) . . . . ?
Cu1 N1 C1 C2 -179.99(18) . . . . ?
N1 C1 C2 C3 -0.5(4) . . . . ?
C1 C2 C3 C4 1.0(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C1 N1 C5 C4 2.1(3) . . . . ?
Cu1 N1 C5 C4 -178.80(19) . . . . ?
C1 N1 C5 C6 -178.1(2) . . . . ?
Cu1 N1 C5 C6 1.0(3) . . . . ?
C3 C4 C5 N1 -1.6(4) . . . . ?
C3 C4 C5 C6 178.6(2) . . . . ?
C7 N2 C6 C5 -149.4(2) . . . . ?
C13 N2 C6 C5 85.7(3) . . . . ?
Cu1 N2 C6 C5 -34.9(2) . . . . ?
N1 C5 C6 N2 23.9(3) . . . . ?
C4 C5 C6 N2 -156.3(2) . . . . ?
C6 N2 C7 C8 152.9(2) . . . . ?
C13 N2 C7 C8 -79.7(3) . . . . ?
Cu1 N2 C7 C8 38.7(2) . . . . ?
C12 N3 C8 C9 -1.1(4) . . . . ?
Cu1 N3 C8 C9 177.1(2) . . . . ?
C12 N3 C8 C7 -178.5(2) . . . . ?
Cu1 N3 C8 C7 -0.3(3) . . . . ?
N2 C7 C8 N3 -26.7(3) . . . . ?
N2 C7 C8 C9 155.9(2) . . . . ?
N3 C8 C9 C10 -0.5(4) . . . . ?
C7 C8 C9 C10 176.7(2) . . . . ?
C8 C9 C10 C11 1.7(4) . . . . ?
C9 C10 C11 C12 -1.3(4) . . . . ?
C8 N3 C12 C11 1.5(4) . . . . ?
Cu1 N3 C12 C11 -176.47(19) . . . . ?
C10 C11 C12 N3 -0.3(4) . . . . ?
C7 N2 C13 C14 156.5(2) . . . . ?
C6 N2 C13 C14 -76.7(3) . . . . ?
Cu1 N2 C13 C14 41.1(2) . . . . ?
N2 C13 C14 C15 -84.0(3) . . . . ?
N2 C13 C14 C19 92.0(3) . . . . ?
C19 C14 C15 C16 -4.3(4) . . . . ?
C13 C14 C15 C16 171.8(2) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C15 C16 C17 C18 3.2(4) . . . . ?
C16 C17 C18 C19 -1.5(4) . . . . ?
C16 C17 C18 C23 177.7(3) . . . . ?
C15 C14 C19 C18 5.9(3) . . . . ?
C13 C14 C19 C18 -170.0(2) . . . . ?
C15 C14 C19 C20 -173.2(2) . . . . ?
C13 C14 C19 C20 11.0(4) . . . . ?
C17 C18 C19 C14 -3.1(4) . . . . ?
C23 C18 C19 C14 177.8(2) . . . . ?
C17 C18 C19 C20 176.0(2) . . . . ?
C23 C18 C19 C20 -3.1(4) . . . . ?
C14 C19 C20 C21 -179.7(2) . . . . ?
C18 C19 C20 C21 1.3(4) . . . . ?
C19 C20 C21 C22 1.0(4) . . . . ?
C20 C21 C22 C23 -1.3(5) . . . . ?
C21 C22 C23 C18 -0.8(5) . . . . ?
C17 C18 C23 C22 -176.2(3) . . . . ?
C19 C18 C23 C22 3.0(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.066
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 0.302 0.177 0.861 19 4 ' '
2 0.802 0.177 0.639 19 4 ' '
3 0.302 0.323 0.361 19 4 ' '
4 0.802 0.323 0.139 19 4 ' '
5 0.198 0.677 0.861 19 4 ' '
6 0.698 0.677 0.639 19 4 ' '
7 0.198 0.823 0.361 19 4 ' '
8 0.698 0.823 0.139 19 4 ' '
_platon_squeeze_details          
;
;
####################################################################### 
# 
# 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_aa
_database_code_depnum_ccdc_archive 'CCDC 1013684'
_audit_update_record             
;
2014-07-12 deposited with the CCDC.
2015-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H28 Cu F6 N3 O2 P'
_chemical_formula_weight         647.04

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   16.570(3)
_cell_length_b                   12.324(3)
_cell_length_c                   14.080(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.64(3)
_cell_angle_gamma                90.00
_cell_volume                     2816.2(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    9107
_cell_measurement_theta_min      2.0750
_cell_measurement_theta_max      27.9024

_exptl_crystal_description       Prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.2000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.2000
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1324
_exptl_absorpt_coefficient_mu    0.904
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8040
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22877
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4958
_reflns_number_gt                4426
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0474P)²+0.7668P] 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         4958
_refine_ls_number_parameters     372
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0788
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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 0.292490(14) 0.604845(18) 0.105293(15) 0.01450(9) Uani 1 1 d . . .
N1 N 0.24972(10) 0.71720(12) 0.18319(11) 0.0154(3) Uani 1 1 d . . .
N2 N 0.23984(9) 0.49808(12) 0.18899(10) 0.0138(3) Uani 1 1 d . . .
N3 N 0.40364(10) 0.53531(13) 0.20276(11) 0.0179(4) Uani 1 1 d . . .
O1 O 0.34741(8) 0.70868(11) 0.03771(9) 0.0207(3) Uani 1 1 d . . .
O2 O 0.28237(8) 0.49710(10) 0.00541(9) 0.0191(3) Uani 1 1 d . . .
C1 C 0.42917(15) 0.77182(18) -0.06978(16) 0.0319(5) Uani 1 1 d . . .
H1A H 0.4024 0.8404 -0.0666 0.048 Uiso 1 1 calc R . .
H1B H 0.4337 0.7575 -0.1355 0.048 Uiso 1 1 calc R . .
H1C H 0.4832 0.7739 -0.0292 0.048 Uiso 1 1 calc R . .
C2 C 0.37936(12) 0.68347(16) -0.03519(13) 0.0196(4) Uani 1 1 d . . .
C3 C 0.37193(13) 0.58392(17) -0.08176(14) 0.0228(5) Uani 1 1 d . . .
H3 H 0.4019 0.5737 -0.1302 0.027 Uiso 1 1 calc R . .
C4 C 0.32324(12) 0.49779(16) -0.06213(13) 0.0186(4) Uani 1 1 d . . .
C5 C 0.31451(15) 0.39732(17) -0.12327(16) 0.0297(5) Uani 1 1 d . . .
H5A H 0.3444 0.3390 -0.0870 0.045 Uiso 1 1 calc R . .
H5B H 0.3362 0.4105 -0.1805 0.045 Uiso 1 1 calc R . .
H5C H 0.2573 0.3781 -0.1415 0.045 Uiso 1 1 calc R . .
C6 C 0.48064(12) 0.57293(18) 0.22867(15) 0.0227(5) Uani 1 1 d . . .
H6 H 0.4941 0.6375 0.2015 0.027 Uiso 1 1 calc R . .
C7 C 0.54076(13) 0.5199(2) 0.29400(15) 0.0297(5) Uani 1 1 d . . .
H7 H 0.5937 0.5485 0.3108 0.036 Uiso 1 1 calc R . .
C8 C 0.52133(14) 0.4240(2) 0.33405(16) 0.0350(6) Uani 1 1 d . . .
H8 H 0.5611 0.3859 0.3774 0.042 Uiso 1 1 calc R . .
C9 C 0.44148(14) 0.38513(18) 0.30855(16) 0.0278(5) Uani 1 1 d . . .
H9 H 0.4265 0.3213 0.3358 0.033 Uiso 1 1 calc R . .
C10 C 0.38447(12) 0.44215(15) 0.24236(13) 0.0167(4) Uani 1 1 d . . .
C11 C 0.29731(12) 0.40427(15) 0.20898(14) 0.0160(4) Uani 1 1 d . . .
H11A H 0.2933 0.3612 0.1506 0.019 Uiso 1 1 calc R . .
H11B H 0.2818 0.3587 0.2585 0.019 Uiso 1 1 calc R . .
C12 C 0.23721(12) 0.55942(15) 0.27959(13) 0.0150(4) Uani 1 1 d . . .
H12A H 0.2895 0.5516 0.3247 0.018 Uiso 1 1 calc R . .
H12B H 0.1944 0.5295 0.3098 0.018 Uiso 1 1 calc R . .
C13 C 0.22035(11) 0.67749(15) 0.25821(13) 0.0148(4) Uani 1 1 d . . .
C14 C 0.17849(12) 0.74248(16) 0.31257(14) 0.0202(4) Uani 1 1 d . . .
H14 H 0.1592 0.7141 0.3650 0.024 Uiso 1 1 calc R . .
C15 C 0.16600(13) 0.85027(17) 0.28716(15) 0.0242(5) Uani 1 1 d . . .
H15 H 0.1374 0.8952 0.3219 0.029 Uiso 1 1 calc R . .
C16 C 0.19618(13) 0.89096(16) 0.20977(15) 0.0236(5) Uani 1 1 d . . .
H16 H 0.1883 0.9634 0.1919 0.028 Uiso 1 1 calc R . .
C17 C 0.23809(12) 0.82258(15) 0.15964(14) 0.0192(4) Uani 1 1 d . . .
H17 H 0.2590 0.8500 0.1080 0.023 Uiso 1 1 calc R . .
C18 C 0.15664(11) 0.45460(15) 0.14200(14) 0.0173(4) Uani 1 1 d . . .
H18A H 0.1378 0.4054 0.1867 0.021 Uiso 1 1 calc R . .
H18B H 0.1619 0.4134 0.0849 0.021 Uiso 1 1 calc R . .
C19 C 0.09297(11) 0.54195(16) 0.11292(13) 0.0170(4) Uani 1 1 d . . .
C20 C 0.09026(12) 0.59290(17) 0.02598(14) 0.0216(5) Uani 1 1 d . . .
H20 H 0.1258 0.5700 -0.0133 0.026 Uiso 1 1 calc R . .
C21 C 0.03581(12) 0.67835(18) -0.00593(15) 0.0265(5) Uani 1 1 d . . .
H21 H 0.0358 0.7115 -0.0653 0.032 Uiso 1 1 calc R . .
C22 C -0.01706(12) 0.71260(17) 0.05030(15) 0.0253(5) Uani 1 1 d . . .
H22 H -0.0525 0.7702 0.0297 0.030 Uiso 1 1 calc R . .
C23 C -0.01860(12) 0.66142(16) 0.13964(14) 0.0202(4) Uani 1 1 d . . .
C24 C 0.03613(12) 0.57385(16) 0.17197(14) 0.0174(4) Uani 1 1 d . . .
C25 C 0.03142(12) 0.52376(17) 0.26169(14) 0.0218(4) Uani 1 1 d . . .
H25 H 0.0653 0.4650 0.2834 0.026 Uiso 1 1 calc R . .
C26 C -0.02220(13) 0.56065(18) 0.31661(15) 0.0269(5) Uani 1 1 d . . .
H26 H -0.0232 0.5279 0.3758 0.032 Uiso 1 1 calc R . .
C27 C -0.07563(13) 0.64731(19) 0.28466(16) 0.0287(5) Uani 1 1 d . . .
H27 H -0.1119 0.6717 0.3226 0.034 Uiso 1 1 calc R . .
C28 C -0.07443(13) 0.69586(18) 0.19793(16) 0.0263(5) Uani 1 1 d . . .
H28 H -0.1107 0.7524 0.1766 0.032 Uiso 1 1 calc R . .
F1 F 0.21031(8) 0.23789(10) 0.02898(9) 0.0320(3) Uani 1 1 d . . .
F2 F 0.34127(8) 0.18502(11) 0.03554(10) 0.0358(3) Uani 1 1 d . . .
F3 F 0.24106(9) 0.14159(10) -0.09395(8) 0.0382(3) Uani 1 1 d . . .
F4 F 0.29905(9) 0.01129(10) 0.01186(9) 0.0392(3) Uani 1 1 d . . .
F5 F 0.16787(8) 0.06402(12) 0.00631(10) 0.0426(4) Uani 1 1 d . . .
F6 F 0.26759(8) 0.10861(11) 0.13531(8) 0.0343(3) Uani 1 1 d . . .
P1 P 0.25472(3) 0.12460(4) 0.02055(4) 0.01941(13) Uani 1 1 d . . .


_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 O2 1.9169(13) . ?
Cu1 O1 1.9290(13) . ?
Cu1 N1 1.9840(15) . ?
Cu1 N2 2.0727(15) . ?
Cu1 N3 2.2338(18) . ?
N1 C13 1.342(2) . ?
N1 C17 1.345(2) . ?
N2 C11 1.488(2) . ?
N2 C12 1.491(2) . ?
N2 C18 1.502(2) . ?
N3 C6 1.337(3) . ?
N3 C10 1.342(2) . ?
O1 C2 1.284(2) . ?
O2 C4 1.274(2) . ?
C1 C2 1.505(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.394(3) . ?
C4 C5 1.498(3) . ?
C6 C7 1.377(3) . ?
C7 C8 1.376(3) . ?
C8 C9 1.384(3) . ?
C9 C10 1.378(3) . ?
C10 C11 1.500(3) . ?
C12 C13 1.501(3) . ?
C13 C14 1.387(3) . ?
C14 C15 1.380(3) . ?
C15 C16 1.382(3) . ?
C16 C17 1.374(3) . ?
C18 C19 1.505(3) . ?
C19 C20 1.368(3) . ?
C19 C24 1.431(3) . ?
C20 C21 1.400(3) . ?
C21 C22 1.361(3) . ?
C22 C23 1.412(3) . ?
C23 C28 1.420(3) . ?
C23 C24 1.424(3) . ?
C24 C25 1.422(3) . ?
C25 C26 1.368(3) . ?
C26 C27 1.402(3) . ?
C27 C28 1.364(3) . ?
F1 P1 1.5938(13) . ?
F2 P1 1.5918(14) . ?
F3 P1 1.5961(12) . ?
F4 P1 1.5939(13) . ?
F5 P1 1.5975(14) . ?
F6 P1 1.5988(13) . ?

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
O2 Cu1 O1 94.46(6) . . ?
O2 Cu1 N1 154.29(6) . . ?
O1 Cu1 N1 93.81(6) . . ?
O2 Cu1 N2 89.59(6) . . ?
O1 Cu1 N2 175.03(6) . . ?
N1 Cu1 N2 83.71(6) . . ?
O2 Cu1 N3 97.14(6) . . ?
O1 Cu1 N3 98.34(6) . . ?
N1 Cu1 N3 105.68(6) . . ?
N2 Cu1 N3 78.27(6) . . ?
C13 N1 C17 119.33(16) . . ?
C13 N1 Cu1 114.05(12) . . ?
C17 N1 Cu1 125.95(13) . . ?
C11 N2 C12 111.10(14) . . ?
C11 N2 C18 107.55(14) . . ?
C12 N2 C18 112.03(14) . . ?
C11 N2 Cu1 105.90(11) . . ?
C12 N2 Cu1 104.65(11) . . ?
C18 N2 Cu1 115.48(11) . . ?
C6 N3 C10 118.42(18) . . ?
C6 N3 Cu1 131.12(14) . . ?
C10 N3 Cu1 110.39(12) . . ?
C2 O1 Cu1 123.04(12) . . ?
C4 O2 Cu1 124.20(12) . . ?
O1 C2 C3 125.53(17) . . ?
O1 C2 C1 115.14(17) . . ?
C3 C2 C1 119.33(17) . . ?
C2 C3 C4 125.47(18) . . ?
O2 C4 C3 124.69(18) . . ?
O2 C4 C5 114.78(17) . . ?
C3 C4 C5 120.51(17) . . ?
N3 C6 C7 122.7(2) . . ?
C8 C7 C6 119.0(2) . . ?
C7 C8 C9 118.8(2) . . ?
C10 C9 C8 119.2(2) . . ?
N3 C10 C9 121.98(19) . . ?
N3 C10 C11 115.44(17) . . ?
C9 C10 C11 122.58(18) . . ?
N2 C11 C10 110.88(15) . . ?
N2 C12 C13 110.88(14) . . ?
N1 C13 C14 121.68(18) . . ?
N1 C13 C12 115.42(15) . . ?
C14 C13 C12 122.89(16) . . ?
C15 C14 C13 118.58(18) . . ?
C14 C15 C16 119.64(18) . . ?
C17 C16 C15 118.91(19) . . ?
N1 C17 C16 121.85(18) . . ?
N2 C18 C19 113.28(15) . . ?
C20 C19 C24 119.14(18) . . ?
C20 C19 C18 117.79(17) . . ?
C24 C19 C18 123.07(17) . . ?
C19 C20 C21 122.32(19) . . ?
C22 C21 C20 119.69(19) . . ?
C21 C22 C23 120.6(2) . . ?
C22 C23 C28 120.82(19) . . ?
C22 C23 C24 119.90(18) . . ?
C28 C23 C24 119.28(19) . . ?
C25 C24 C23 117.85(17) . . ?
C25 C24 C19 123.87(18) . . ?
C23 C24 C19 118.28(17) . . ?
C26 C25 C24 121.1(2) . . ?
C25 C26 C27 120.8(2) . . ?
C28 C27 C26 119.94(19) . . ?
C27 C28 C23 121.0(2) . . ?
F2 P1 F1 89.86(7) . . ?
F2 P1 F4 90.18(8) . . ?
F1 P1 F4 179.87(9) . . ?
F2 P1 F3 90.74(8) . . ?
F1 P1 F3 89.24(7) . . ?
F4 P1 F3 90.63(7) . . ?
F2 P1 F5 179.60(8) . . ?
F1 P1 F5 90.05(8) . . ?
F4 P1 F5 89.91(8) . . ?
F3 P1 F5 89.65(8) . . ?
F2 P1 F6 89.47(8) . . ?
F1 P1 F6 90.12(7) . . ?
F4 P1 F6 90.00(7) . . ?
F3 P1 F6 179.33(8) . . ?
F5 P1 F6 90.14(8) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.059
####################################################################### 
# 
# 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_aa
_database_code_depnum_ccdc_archive 'CCDC 1013685'
_audit_update_record             
;
2014-07-12 deposited with the CCDC.
2015-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H46 Cl2 Cu2 F12 N6 O0 P2'
_chemical_formula_weight         1194.83
_chemical_absolute_configuration R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   14.286(3)
_cell_length_b                   15.106(3)
_cell_length_c                   23.050(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4974.3(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4048
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      27.9

_exptl_crystal_description       Prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2424
_exptl_absorpt_coefficient_mu    1.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9847
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            36824
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         25.01
_reflns_number_total             8749
_reflns_number_gt                8056
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0683P)²+4.5221P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00
_refine_ls_number_reflns         8749
_refine_ls_number_parameters     651
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
Cl1 Cl 0.36555(7) 0.44051(6) 0.50856(5) 0.0240(2) Uani 1 1 d . . .
Cu2 Cu 0.56698(3) 0.41287(3) 0.50405(2) 0.01751(12) Uani 1 1 d . . .
C38 C 0.6314(3) 0.2197(3) 0.4993(2) 0.0240(8) Uani 1 1 d . . .
H38 H 0.6722 0.2462 0.4699 0.029 Uiso 1 1 calc R . .
P2 P 0.60401(10) 0.52353(9) 0.85936(5) 0.0335(3) Uani 1 1 d . . .
N1 N 0.4039(3) 0.5931(3) 0.41757(14) 0.0231(8) Uani 1 1 d . . .
N2 N 0.4106(2) 0.7212(2) 0.50022(15) 0.0212(7) Uani 1 1 d . . .
N3 N 0.4070(3) 0.6065(3) 0.58844(14) 0.0221(8) Uani 1 1 d . . .
N4 N 0.5602(2) 0.3975(2) 0.58820(14) 0.0195(8) Uani 1 1 d . . .
N5 N 0.5420(2) 0.2779(2) 0.50333(15) 0.0195(7) Uani 1 1 d . . .
N6 N 0.5707(3) 0.3966(3) 0.41863(14) 0.0221(8) Uani 1 1 d . . .
Cl2 Cl 0.59547(6) 0.56001(6) 0.50334(4) 0.0214(2) Uani 1 1 d . . .
C1 C 0.3798(4) 0.5289(4) 0.3794(2) 0.0333(12) Uani 1 1 d . . .
H1 H 0.3562 0.4753 0.3929 0.040 Uiso 1 1 calc R . .
C2 C 0.3904(4) 0.5428(4) 0.3202(2) 0.0411(14) Uani 1 1 d . . .
H2 H 0.3727 0.4987 0.2942 0.049 Uiso 1 1 calc R . .
C3 C 0.4264(4) 0.6204(4) 0.2997(2) 0.0443(15) Uani 1 1 d . . .
H3 H 0.4349 0.6290 0.2601 0.053 Uiso 1 1 calc R . .
C4 C 0.4504(4) 0.6868(4) 0.3395(2) 0.0392(14) Uani 1 1 d . . .
H4 H 0.4749 0.7405 0.3269 0.047 Uiso 1 1 calc R . .
C5 C 0.4369(3) 0.6706(4) 0.39814(18) 0.0274(11) Uani 1 1 d . . .
C6 C 0.4624(3) 0.7373(3) 0.44438(18) 0.0256(10) Uani 1 1 d . . .
H6A H 0.5292 0.7344 0.4517 0.031 Uiso 1 1 calc R . .
H6B H 0.4480 0.7964 0.4304 0.031 Uiso 1 1 calc R . .
C7 C 0.4688(3) 0.7446(3) 0.55076(17) 0.0231(10) Uani 1 1 d . . .
H7A H 0.4593 0.8064 0.5607 0.028 Uiso 1 1 calc R . .
H7B H 0.5344 0.7362 0.5415 0.028 Uiso 1 1 calc R . .
C8 C 0.4419(3) 0.6866(3) 0.60178(18) 0.0214(10) Uani 1 1 d . . .
C9 C 0.4554(4) 0.7120(4) 0.65862(19) 0.0329(12) Uani 1 1 d . . .
H9 H 0.4798 0.7675 0.6673 0.039 Uiso 1 1 calc R . .
C10 C 0.4319(4) 0.6535(4) 0.70278(19) 0.0368(12) Uani 1 1 d . . .
H10 H 0.4412 0.6689 0.7414 0.044 Uiso 1 1 calc R . .
C11 C 0.3947(4) 0.5727(4) 0.68879(19) 0.0370(12) Uani 1 1 d . . .
H11 H 0.3772 0.5333 0.7178 0.044 Uiso 1 1 calc R . .
C12 C 0.3837(3) 0.5506(3) 0.63118(18) 0.0272(10) Uani 1 1 d . . .
H12 H 0.3595 0.4954 0.6217 0.033 Uiso 1 1 calc R . .
C13 C 0.2722(3) 0.7805(3) 0.55943(19) 0.0302(11) Uani 1 1 d . . .
H13A H 0.2629 0.7230 0.5761 0.045 Uiso 1 1 calc R . .
H13B H 0.2130 0.8101 0.5559 0.045 Uiso 1 1 calc R . .
H13C H 0.3128 0.8146 0.5840 0.045 Uiso 1 1 calc R . .
C14 C 0.3169(3) 0.7709(3) 0.4993(2) 0.0235(8) Uani 1 1 d . . .
H14 H 0.3286 0.8305 0.4842 0.028 Uiso 1 1 calc R . .
C15 C 0.2501(3) 0.7239(3) 0.45685(18) 0.0225(9) Uani 1 1 d . . .
C16 C 0.2057(3) 0.6479(3) 0.4747(2) 0.0269(10) Uani 1 1 d . . .
H16 H 0.2106 0.6306 0.5133 0.032 Uiso 1 1 calc R . .
C17 C 0.1530(3) 0.5955(3) 0.4362(2) 0.0286(10) Uani 1 1 d . . .
H17 H 0.1221 0.5456 0.4500 0.034 Uiso 1 1 calc R . .
C18 C 0.1471(3) 0.6169(3) 0.3799(2) 0.0321(11) Uani 1 1 d . . .
H18 H 0.1160 0.5794 0.3543 0.039 Uiso 1 1 calc R . .
C19 C 0.1881(3) 0.6970(4) 0.35880(19) 0.0299(11) Uani 1 1 d . . .
C20 C 0.1794(4) 0.7230(4) 0.2995(2) 0.0418(13) Uani 1 1 d . . .
H20 H 0.1497 0.6855 0.2733 0.050 Uiso 1 1 calc R . .
C21 C 0.2142(4) 0.8024(4) 0.2808(2) 0.0453(15) Uani 1 1 d . . .
H21 H 0.2078 0.8189 0.2422 0.054 Uiso 1 1 calc R . .
C22 C 0.2594(4) 0.8589(4) 0.3200(2) 0.0405(13) Uani 1 1 d . . .
H22 H 0.2821 0.9132 0.3071 0.049 Uiso 1 1 calc R . .
C23 C 0.2708(4) 0.8359(3) 0.3770(2) 0.0333(12) Uani 1 1 d . . .
H23 H 0.3007 0.8749 0.4021 0.040 Uiso 1 1 calc R . .
C24 C 0.2377(3) 0.7535(3) 0.39864(19) 0.0256(10) Uani 1 1 d . . .
C25 C 0.5932(3) 0.4546(3) 0.62844(17) 0.0234(10) Uani 1 1 d . . .
H25 H 0.6213 0.5070 0.6163 0.028 Uiso 1 1 calc R . .
C26 C 0.5861(4) 0.4371(3) 0.68752(19) 0.0312(12) Uani 1 1 d . . .
H26 H 0.6093 0.4768 0.7147 0.037 Uiso 1 1 calc R . .
C27 C 0.5442(4) 0.3600(4) 0.70464(19) 0.0350(12) Uani 1 1 d . . .
H27 H 0.5378 0.3474 0.7439 0.042 Uiso 1 1 calc R . .
C28 C 0.5108(4) 0.2998(3) 0.66321(18) 0.0295(11) Uani 1 1 d . . .
H28 H 0.4823 0.2471 0.6743 0.035 Uiso 1 1 calc R . .
C29 C 0.5216(3) 0.3212(3) 0.60558(18) 0.0214(10) Uani 1 1 d . . .
C30 C 0.4878(3) 0.2612(3) 0.55714(17) 0.0210(9) Uani 1 1 d . . .
H30A H 0.4952 0.1999 0.5687 0.025 Uiso 1 1 calc R . .
H30B H 0.4219 0.2719 0.5499 0.025 Uiso 1 1 calc R . .
C31 C 0.4854(3) 0.2683(3) 0.44979(17) 0.0234(10) Uani 1 1 d . . .
H31A H 0.4224 0.2899 0.4565 0.028 Uiso 1 1 calc R . .
H31B H 0.4815 0.2063 0.4390 0.028 Uiso 1 1 calc R . .
C32 C 0.5300(3) 0.3197(3) 0.40196(18) 0.0223(10) Uani 1 1 d . . .
C33 C 0.5288(4) 0.2950(4) 0.34434(19) 0.0330(12) Uani 1 1 d . . .
H33 H 0.5022 0.2414 0.3332 0.040 Uiso 1 1 calc R . .
C34 C 0.5680(4) 0.3512(4) 0.30292(19) 0.0385(13) Uani 1 1 d . . .
H34 H 0.5660 0.3365 0.2638 0.046 Uiso 1 1 calc R . .
C35 C 0.6095(4) 0.4285(4) 0.32065(19) 0.0347(12) Uani 1 1 d . . .
H35 H 0.6371 0.4664 0.2938 0.042 Uiso 1 1 calc R . .
C36 C 0.6094(3) 0.4490(3) 0.37894(19) 0.0281(11) Uani 1 1 d . . .
H36 H 0.6376 0.5014 0.3910 0.034 Uiso 1 1 calc R . .
C37 C 0.6090(4) 0.1249(3) 0.4796(2) 0.0360(12) Uani 1 1 d . . .
H37A H 0.6624 0.0876 0.4863 0.054 Uiso 1 1 calc R . .
H37B H 0.5942 0.1249 0.4390 0.054 Uiso 1 1 calc R . .
H37C H 0.5565 0.1028 0.5012 0.054 Uiso 1 1 calc R . .
C39 C 0.6841(3) 0.2221(3) 0.5571(2) 0.0289(10) Uani 1 1 d . . .
C40 C 0.6715(4) 0.1568(3) 0.5982(2) 0.0359(12) Uani 1 1 d . . .
H40 H 0.6328 0.1092 0.5893 0.043 Uiso 1 1 calc R . .
C41 C 0.7144(4) 0.1592(4) 0.6525(2) 0.0406(13) Uani 1 1 d . . .
H41 H 0.7066 0.1124 0.6783 0.049 Uiso 1 1 calc R . .
C42 C 0.7669(4) 0.2291(4) 0.6676(2) 0.0422(14) Uani 1 1 d . . .
H42 H 0.7924 0.2315 0.7047 0.051 Uiso 1 1 calc R . .
C43 C 0.7850(3) 0.3013(4) 0.6273(2) 0.0319(11) Uani 1 1 d . . .
C44 C 0.8394(4) 0.3720(4) 0.6412(2) 0.0435(14) Uani 1 1 d . . .
H44 H 0.8644 0.3757 0.6784 0.052 Uiso 1 1 calc R . .
C45 C 0.8584(4) 0.4375(4) 0.6027(3) 0.0431(13) Uani 1 1 d . . .
H45 H 0.8936 0.4863 0.6139 0.052 Uiso 1 1 calc R . .
C46 C 0.8244(3) 0.4309(3) 0.5451(2) 0.0362(12) Uani 1 1 d . . .
H46 H 0.8402 0.4744 0.5182 0.043 Uiso 1 1 calc R . .
C47 C 0.7685(3) 0.3616(3) 0.5284(2) 0.0312(11) Uani 1 1 d . . .
H47 H 0.7461 0.3584 0.4906 0.037 Uiso 1 1 calc R . .
C48 C 0.7446(3) 0.2933(3) 0.5700(2) 0.0287(10) Uani 1 1 d . . .
F1 F 0.5414(3) 0.9388(3) 0.41172(17) 0.0757(12) Uani 1 1 d . . .
F2 F 0.6172(3) 0.8285(3) 0.36503(18) 0.0764(12) Uani 1 1 d . . .
F3 F 0.5038(3) 0.9081(3) 0.3219(2) 0.0932(15) Uani 1 1 d . . .
F4 F 0.6564(4) 0.9225(4) 0.29463(16) 0.117(2) Uani 1 1 d . . .
F5 F 0.5787(3) 1.0346(3) 0.33940(17) 0.0786(12) Uani 1 1 d . . .
F6 F 0.6873(3) 0.9572(3) 0.38862(18) 0.0849(14) Uani 1 1 d . . .
F7 F 0.5760(3) 0.4257(2) 0.84767(17) 0.0641(10) Uani 1 1 d . . .
F8 F 0.5375(3) 0.5307(3) 0.91194(14) 0.0645(10) Uani 1 1 d . . .
F9 F 0.5280(3) 0.5589(3) 0.81765(17) 0.0784(12) Uani 1 1 d . . .
F10 F 0.6442(3) 0.6215(3) 0.87182(19) 0.0778(13) Uani 1 1 d . . .
F11 F 0.6814(3) 0.5153(3) 0.80913(16) 0.0720(12) Uani 1 1 d . . .
F12 F 0.6855(3) 0.4903(3) 0.90399(17) 0.0767(13) Uani 1 1 d . . .
P1 P 0.59811(11) 0.93224(12) 0.35048(6) 0.0481(4) Uani 1 1 d . . .
Cu1 Cu 0.39907(3) 0.58566(3) 0.50363(2) 0.01883(13) Uani 1 1 d . . .


_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
Cl1 Cu1 2.2472(12) . ?
Cu2 N4 1.956(3) . ?
Cu2 N6 1.985(3) . ?
Cu2 N5 2.069(3) . ?
Cu2 Cl2 2.2598(11) . ?
C38 C39 1.530(6) . ?
C38 C37 1.537(6) . ?
C38 N5 1.553(5) . ?
C38 H38 0.9800 . ?
P2 F8 1.544(3) . ?
P2 F9 1.545(4) . ?
P2 F7 1.555(4) . ?
P2 F11 1.605(4) . ?
P2 F10 1.613(4) . ?
P2 F12 1.633(4) . ?
N1 C5 1.339(6) . ?
N1 C1 1.354(6) . ?
N1 Cu1 1.988(3) . ?
N2 C7 1.474(5) . ?
N2 C6 1.504(5) . ?
N2 C14 1.535(5) . ?
N2 Cu1 2.056(3) . ?
N3 C12 1.339(6) . ?
N3 C8 1.344(6) . ?
N3 Cu1 1.983(3) . ?
N4 C29 1.341(6) . ?
N4 C25 1.351(6) . ?
N5 C31 1.483(5) . ?
N5 C30 1.484(5) . ?
N6 C36 1.330(6) . ?
N6 C32 1.355(6) . ?
C1 C2 1.390(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.364(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.511(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.517(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.379(6) . ?
C9 C10 1.390(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.368(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.534(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.539(6) . ?
C14 H14 0.9800 . ?
C15 C16 1.374(6) . ?
C15 C24 1.425(6) . ?
C16 C17 1.407(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.340(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.430(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.427(6) . ?
C19 C24 1.439(7) . ?
C20 C21 1.369(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.401(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.369(7) . ?
C22 H22 0.9300 . ?
C23 C24 1.422(7) . ?
C23 H23 0.9300 . ?
C25 C26 1.391(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.368(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.402(7) . ?
C27 H27 0.9300 . ?
C28 C29 1.376(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.516(6) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.492(6) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.380(6) . ?
C33 C34 1.395(7) . ?
C33 H33 0.9300 . ?
C34 C35 1.372(8) . ?
C34 H34 0.9300 . ?
C35 C36 1.379(6) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C39 C40 1.380(7) . ?
C39 C48 1.412(7) . ?
C40 C41 1.395(7) . ?
C40 H40 0.9300 . ?
C41 C42 1.341(8) . ?
C41 H41 0.9300 . ?
C42 C43 1.456(8) . ?
C42 H42 0.9300 . ?
C43 C44 1.359(8) . ?
C43 C48 1.446(6) . ?
C44 C45 1.357(8) . ?
C44 H44 0.9300 . ?
C45 C46 1.416(7) . ?
C45 H45 0.9300 . ?
C46 C47 1.373(7) . ?
C46 H46 0.9300 . ?
C47 C48 1.449(7) . ?
C47 H47 0.9300 . ?
F1 P1 1.631(4) . ?
F2 P1 1.626(5) . ?
F3 P1 1.544(4) . ?
F4 P1 1.540(4) . ?
F5 P1 1.591(5) . ?
F6 P1 1.593(4) . ?

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
N4 Cu2 N6 166.05(14) . . ?
N4 Cu2 N5 83.27(14) . . ?
N6 Cu2 N5 82.82(15) . . ?
N4 Cu2 Cl2 97.62(11) . . ?
N6 Cu2 Cl2 96.28(11) . . ?
N5 Cu2 Cl2 179.01(10) . . ?
C39 C38 C37 112.4(4) . . ?
C39 C38 N5 109.8(3) . . ?
C37 C38 N5 112.0(3) . . ?
C39 C38 H38 107.4 . . ?
C37 C38 H38 107.4 . . ?
N5 C38 H38 107.4 . . ?
F8 P2 F9 91.8(2) . . ?
F8 P2 F7 92.5(2) . . ?
F9 P2 F7 92.3(3) . . ?
F8 P2 F11 174.4(2) . . ?
F9 P2 F11 93.5(2) . . ?
F7 P2 F11 88.8(2) . . ?
F8 P2 F10 90.9(2) . . ?
F9 P2 F10 92.5(3) . . ?
F7 P2 F10 174.0(3) . . ?
F11 P2 F10 87.4(2) . . ?
F8 P2 F12 88.1(2) . . ?
F9 P2 F12 177.7(3) . . ?
F7 P2 F12 90.0(2) . . ?
F11 P2 F12 86.5(2) . . ?
F10 P2 F12 85.2(3) . . ?
C5 N1 C1 119.9(4) . . ?
C5 N1 Cu1 113.3(3) . . ?
C1 N1 Cu1 126.8(3) . . ?
C7 N2 C6 111.1(3) . . ?
C7 N2 C14 112.7(3) . . ?
C6 N2 C14 109.7(3) . . ?
C7 N2 Cu1 104.7(2) . . ?
C6 N2 Cu1 103.5(3) . . ?
C14 N2 Cu1 114.7(2) . . ?
C12 N3 C8 119.4(4) . . ?
C12 N3 Cu1 127.7(3) . . ?
C8 N3 Cu1 112.9(3) . . ?
C29 N4 C25 119.2(4) . . ?
C29 N4 Cu2 114.7(3) . . ?
C25 N4 Cu2 126.0(3) . . ?
C31 N5 C30 113.2(3) . . ?
C31 N5 C38 110.1(3) . . ?
C30 N5 C38 112.5(3) . . ?
C31 N5 Cu2 101.4(2) . . ?
C30 N5 Cu2 104.5(2) . . ?
C38 N5 Cu2 114.6(2) . . ?
C36 N6 C32 119.6(4) . . ?
C36 N6 Cu2 128.3(3) . . ?
C32 N6 Cu2 112.1(3) . . ?
N1 C1 C2 120.2(5) . . ?
N1 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 120.7(5) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 118.8(5) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 118.5(5) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
N1 C5 C4 122.0(5) . . ?
N1 C5 C6 115.6(4) . . ?
C4 C5 C6 122.4(5) . . ?
N2 C6 C5 112.2(4) . . ?
N2 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 C8 109.3(4) . . ?
N2 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
N2 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
N3 C8 C9 121.3(4) . . ?
N3 C8 C7 115.9(4) . . ?
C9 C8 C7 122.7(4) . . ?
C8 C9 C10 119.0(5) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C11 C10 C9 119.2(4) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 119.2(5) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
N3 C12 C11 121.9(5) . . ?
N3 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C13 C14 N2 113.4(3) . . ?
C13 C14 C15 111.1(4) . . ?
N2 C14 C15 108.9(3) . . ?
C13 C14 H14 107.7 . . ?
N2 C14 H14 107.7 . . ?
C15 C14 H14 107.7 . . ?
C16 C15 C24 119.0(4) . . ?
C16 C15 C14 118.8(4) . . ?
C24 C15 C14 122.0(4) . . ?
C15 C16 C17 122.0(4) . . ?
C15 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C18 C17 C16 120.5(5) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 120.5(5) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 121.5(5) . . ?
C20 C19 C24 119.4(5) . . ?
C18 C19 C24 119.1(4) . . ?
C21 C20 C19 120.7(5) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 119.9(5) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 121.3(5) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C24 121.3(5) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C15 124.3(4) . . ?
C23 C24 C19 117.3(4) . . ?
C15 C24 C19 118.4(4) . . ?
N4 C25 C26 121.7(5) . . ?
N4 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C27 C26 C25 118.5(5) . . ?
C27 C26 H26 120.8 . . ?
C25 C26 H26 120.8 . . ?
C26 C27 C28 120.3(4) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C29 C28 C27 117.9(5) . . ?
C29 C28 H28 121.1 . . ?
C27 C28 H28 121.1 . . ?
N4 C29 C28 122.4(4) . . ?
N4 C29 C30 115.1(4) . . ?
C28 C29 C30 122.4(4) . . ?
N5 C30 C29 110.4(3) . . ?
N5 C30 H30A 109.6 . . ?
C29 C30 H30A 109.6 . . ?
N5 C30 H30B 109.6 . . ?
C29 C30 H30B 109.6 . . ?
H30A C30 H30B 108.1 . . ?
N5 C31 C32 109.3(4) . . ?
N5 C31 H31A 109.8 . . ?
C32 C31 H31A 109.8 . . ?
N5 C31 H31B 109.8 . . ?
C32 C31 H31B 109.8 . . ?
H31A C31 H31B 108.3 . . ?
N6 C32 C33 120.7(4) . . ?
N6 C32 C31 114.9(4) . . ?
C33 C32 C31 124.4(4) . . ?
C32 C33 C34 119.2(5) . . ?
C32 C33 H33 120.4 . . ?
C34 C33 H33 120.4 . . ?
C35 C34 C33 119.2(4) . . ?
C35 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
C34 C35 C36 118.8(5) . . ?
C34 C35 H35 120.6 . . ?
C36 C35 H35 120.6 . . ?
N6 C36 C35 122.5(5) . . ?
N6 C36 H36 118.8 . . ?
C35 C36 H36 118.8 . . ?
C38 C37 H37A 109.5 . . ?
C38 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C38 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C40 C39 C48 118.6(5) . . ?
C40 C39 C38 121.1(5) . . ?
C48 C39 C38 120.2(4) . . ?
C39 C40 C41 122.8(5) . . ?
C39 C40 H40 118.6 . . ?
C41 C40 H40 118.6 . . ?
C42 C41 C40 119.9(5) . . ?
C42 C41 H41 120.1 . . ?
C40 C41 H41 120.1 . . ?
C41 C42 C43 121.7(5) . . ?
C41 C42 H42 119.2 . . ?
C43 C42 H42 119.2 . . ?
C44 C43 C48 120.6(5) . . ?
C44 C43 C42 122.7(5) . . ?
C48 C43 C42 116.6(5) . . ?
C45 C44 C43 122.2(5) . . ?
C45 C44 H44 118.9 . . ?
C43 C44 H44 118.9 . . ?
C44 C45 C46 119.6(5) . . ?
C44 C45 H45 120.2 . . ?
C46 C45 H45 120.2 . . ?
C47 C46 C45 121.0(5) . . ?
C47 C46 H46 119.5 . . ?
C45 C46 H46 119.5 . . ?
C46 C47 C48 119.6(5) . . ?
C46 C47 H47 120.2 . . ?
C48 C47 H47 120.2 . . ?
C39 C48 C43 120.1(5) . . ?
C39 C48 C47 123.1(4) . . ?
C43 C48 C47 116.8(5) . . ?
F4 P1 F3 95.3(3) . . ?
F4 P1 F5 93.0(3) . . ?
F3 P1 F5 90.5(3) . . ?
F4 P1 F6 93.0(3) . . ?
F3 P1 F6 171.7(3) . . ?
F5 P1 F6 89.9(3) . . ?
F4 P1 F2 89.4(3) . . ?
F3 P1 F2 90.4(3) . . ?
F5 P1 F2 177.3(2) . . ?
F6 P1 F2 88.9(3) . . ?
F4 P1 F1 176.4(3) . . ?
F3 P1 F1 87.2(3) . . ?
F5 P1 F1 89.6(2) . . ?
F6 P1 F1 84.6(2) . . ?
F2 P1 F1 87.9(2) . . ?
N3 Cu1 N1 166.55(15) . . ?
N3 Cu1 N2 82.82(15) . . ?
N1 Cu1 N2 84.42(15) . . ?
N3 Cu1 Cl1 96.73(12) . . ?
N1 Cu1 Cl1 96.49(12) . . ?
N2 Cu1 Cl1 172.26(10) . . ?

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
N6 Cu2 N4 C29 -20.6(7) . . . . ?
N5 Cu2 N4 C29 -15.9(3) . . . . ?
Cl2 Cu2 N4 C29 164.5(3) . . . . ?
N6 Cu2 N4 C25 157.2(5) . . . . ?
N5 Cu2 N4 C25 161.8(4) . . . . ?
Cl2 Cu2 N4 C25 -17.7(4) . . . . ?
C39 C38 N5 C31 -173.9(3) . . . . ?
C37 C38 N5 C31 -48.2(5) . . . . ?
C39 C38 N5 C30 -46.7(4) . . . . ?
C37 C38 N5 C30 79.0(4) . . . . ?
C39 C38 N5 Cu2 72.6(4) . . . . ?
C37 C38 N5 Cu2 -161.8(3) . . . . ?
N4 Cu2 N5 C31 146.3(3) . . . . ?
N6 Cu2 N5 C31 -34.8(3) . . . . ?
Cl2 Cu2 N5 C31 -60(6) . . . . ?
N4 Cu2 N5 C30 28.4(2) . . . . ?
N6 Cu2 N5 C30 -152.7(3) . . . . ?
Cl2 Cu2 N5 C30 -177(100) . . . . ?
N4 Cu2 N5 C38 -95.2(3) . . . . ?
N6 Cu2 N5 C38 83.7(3) . . . . ?
Cl2 Cu2 N5 C38 59(6) . . . . ?
N4 Cu2 N6 C36 -154.9(5) . . . . ?
N5 Cu2 N6 C36 -159.6(4) . . . . ?
Cl2 Cu2 N6 C36 20.0(4) . . . . ?
N4 Cu2 N6 C32 22.7(7) . . . . ?
N5 Cu2 N6 C32 18.1(3) . . . . ?
Cl2 Cu2 N6 C32 -162.3(3) . . . . ?
C5 N1 C1 C2 0.8(7) . . . . ?
Cu1 N1 C1 C2 -177.5(4) . . . . ?
N1 C1 C2 C3 1.1(8) . . . . ?
C1 C2 C3 C4 -1.6(9) . . . . ?
C2 C3 C4 C5 0.3(8) . . . . ?
C1 N1 C5 C4 -2.1(7) . . . . ?
Cu1 N1 C5 C4 176.4(4) . . . . ?
C1 N1 C5 C6 -179.5(4) . . . . ?
Cu1 N1 C5 C6 -1.0(5) . . . . ?
C3 C4 C5 N1 1.6(8) . . . . ?
C3 C4 C5 C6 178.8(5) . . . . ?
C7 N2 C6 C5 146.1(4) . . . . ?
C14 N2 C6 C5 -88.6(4) . . . . ?
Cu1 N2 C6 C5 34.2(4) . . . . ?
N1 C5 C6 N2 -23.9(6) . . . . ?
C4 C5 C6 N2 158.7(4) . . . . ?
C6 N2 C7 C8 -150.0(4) . . . . ?
C14 N2 C7 C8 86.4(4) . . . . ?
Cu1 N2 C7 C8 -38.9(4) . . . . ?
C12 N3 C8 C9 0.8(7) . . . . ?
Cu1 N3 C8 C9 -178.0(4) . . . . ?
C12 N3 C8 C7 178.4(4) . . . . ?
Cu1 N3 C8 C7 -0.4(5) . . . . ?
N2 C7 C8 N3 27.8(5) . . . . ?
N2 C7 C8 C9 -154.7(4) . . . . ?
N3 C8 C9 C10 -0.3(7) . . . . ?
C7 C8 C9 C10 -177.7(5) . . . . ?
C8 C9 C10 C11 -0.9(8) . . . . ?
C9 C10 C11 C12 1.6(8) . . . . ?
C8 N3 C12 C11 -0.2(7) . . . . ?
Cu1 N3 C12 C11 178.5(4) . . . . ?
C10 C11 C12 N3 -1.1(8) . . . . ?
C7 N2 C14 C13 -39.3(5) . . . . ?
C6 N2 C14 C13 -163.6(4) . . . . ?
Cu1 N2 C14 C13 80.4(4) . . . . ?
C7 N2 C14 C15 -163.5(3) . . . . ?
C6 N2 C14 C15 72.1(4) . . . . ?
Cu1 N2 C14 C15 -43.8(4) . . . . ?
C13 C14 C15 C16 -47.1(5) . . . . ?
N2 C14 C15 C16 78.4(5) . . . . ?
C13 C14 C15 C24 137.0(4) . . . . ?
N2 C14 C15 C24 -97.4(5) . . . . ?
C24 C15 C16 C17 4.0(7) . . . . ?
C14 C15 C16 C17 -172.0(4) . . . . ?
C15 C16 C17 C18 2.2(7) . . . . ?
C16 C17 C18 C19 -4.9(7) . . . . ?
C17 C18 C19 C20 -177.4(5) . . . . ?
C17 C18 C19 C24 1.3(7) . . . . ?
C18 C19 C20 C21 176.0(5) . . . . ?
C24 C19 C20 C21 -2.7(8) . . . . ?
C19 C20 C21 C22 0.3(9) . . . . ?
C20 C21 C22 C23 0.9(9) . . . . ?
C21 C22 C23 C24 0.4(8) . . . . ?
C22 C23 C24 C15 177.7(5) . . . . ?
C22 C23 C24 C19 -2.7(7) . . . . ?
C16 C15 C24 C23 172.4(4) . . . . ?
C14 C15 C24 C23 -11.8(7) . . . . ?
C16 C15 C24 C19 -7.3(6) . . . . ?
C14 C15 C24 C19 168.6(4) . . . . ?
C20 C19 C24 C23 3.8(7) . . . . ?
C18 C19 C24 C23 -174.9(4) . . . . ?
C20 C19 C24 C15 -176.5(4) . . . . ?
C18 C19 C24 C15 4.7(7) . . . . ?
C29 N4 C25 C26 -1.5(7) . . . . ?
Cu2 N4 C25 C26 -179.1(3) . . . . ?
N4 C25 C26 C27 -0.3(7) . . . . ?
C25 C26 C27 C28 1.1(8) . . . . ?
C26 C27 C28 C29 -0.1(8) . . . . ?
C25 N4 C29 C28 2.5(7) . . . . ?
Cu2 N4 C29 C28 -179.6(4) . . . . ?
C25 N4 C29 C30 -179.3(4) . . . . ?
Cu2 N4 C29 C30 -1.4(5) . . . . ?
C27 C28 C29 N4 -1.7(7) . . . . ?
C27 C28 C29 C30 -179.8(5) . . . . ?
C31 N5 C30 C29 -145.3(4) . . . . ?
C38 N5 C30 C29 89.2(4) . . . . ?
Cu2 N5 C30 C29 -35.8(4) . . . . ?
N4 C29 C30 N5 26.5(5) . . . . ?
C28 C29 C30 N5 -155.3(4) . . . . ?
C30 N5 C31 C32 157.1(4) . . . . ?
C38 N5 C31 C32 -76.1(4) . . . . ?
Cu2 N5 C31 C32 45.7(4) . . . . ?
C36 N6 C32 C33 0.3(7) . . . . ?
Cu2 N6 C32 C33 -177.6(4) . . . . ?
C36 N6 C32 C31 -177.5(4) . . . . ?
Cu2 N6 C32 C31 4.6(5) . . . . ?
N5 C31 C32 N6 -35.9(5) . . . . ?
N5 C31 C32 C33 146.3(5) . . . . ?
N6 C32 C33 C34 -1.6(8) . . . . ?
C31 C32 C33 C34 176.1(5) . . . . ?
C32 C33 C34 C35 2.1(8) . . . . ?
C33 C34 C35 C36 -1.3(8) . . . . ?
C32 N6 C36 C35 0.5(7) . . . . ?
Cu2 N6 C36 C35 178.0(4) . . . . ?
C34 C35 C36 N6 0.0(8) . . . . ?
C37 C38 C39 C40 -29.6(6) . . . . ?
N5 C38 C39 C40 95.8(5) . . . . ?
C37 C38 C39 C48 152.4(4) . . . . ?
N5 C38 C39 C48 -82.2(5) . . . . ?
C48 C39 C40 C41 1.5(7) . . . . ?
C38 C39 C40 C41 -176.5(4) . . . . ?
C39 C40 C41 C42 3.2(8) . . . . ?
C40 C41 C42 C43 -3.5(8) . . . . ?
C41 C42 C43 C44 -178.8(5) . . . . ?
C41 C42 C43 C48 -0.9(7) . . . . ?
C48 C43 C44 C45 -0.2(8) . . . . ?
C42 C43 C44 C45 177.7(5) . . . . ?
C43 C44 C45 C46 -2.8(9) . . . . ?
C44 C45 C46 C47 3.2(8) . . . . ?
C45 C46 C47 C48 -0.6(7) . . . . ?
C40 C39 C48 C43 -5.9(7) . . . . ?
C38 C39 C48 C43 172.1(4) . . . . ?
C40 C39 C48 C47 175.0(4) . . . . ?
C38 C39 C48 C47 -7.0(6) . . . . ?
C44 C43 C48 C39 -176.5(5) . . . . ?
C42 C43 C48 C39 5.6(7) . . . . ?
C44 C43 C48 C47 2.7(7) . . . . ?
C42 C43 C48 C47 -175.3(4) . . . . ?
C46 C47 C48 C39 176.9(4) . . . . ?
C46 C47 C48 C43 -2.2(6) . . . . ?
C12 N3 Cu1 N1 -178.2(5) . . . . ?
C8 N3 Cu1 N1 0.5(8) . . . . ?
C12 N3 Cu1 N2 163.3(4) . . . . ?
C8 N3 Cu1 N2 -18.1(3) . . . . ?
C12 N3 Cu1 Cl1 -9.0(4) . . . . ?
C8 N3 Cu1 Cl1 169.7(3) . . . . ?
C5 N1 Cu1 N3 -1.3(8) . . . . ?
C1 N1 Cu1 N3 177.1(5) . . . . ?
C5 N1 Cu1 N2 17.2(3) . . . . ?
C1 N1 Cu1 N2 -164.4(4) . . . . ?
C5 N1 Cu1 Cl1 -170.5(3) . . . . ?
C1 N1 Cu1 Cl1 7.9(4) . . . . ?
C7 N2 Cu1 N3 31.6(3) . . . . ?
C6 N2 Cu1 N3 148.1(3) . . . . ?
C14 N2 Cu1 N3 -92.5(3) . . . . ?
C7 N2 Cu1 N1 -144.2(3) . . . . ?
C6 N2 Cu1 N1 -27.7(3) . . . . ?
C14 N2 Cu1 N1 91.8(3) . . . . ?
C7 N2 Cu1 Cl1 118.7(7) . . . . ?
C6 N2 Cu1 Cl1 -124.8(7) . . . . ?
C14 N2 Cu1 Cl1 -5.3(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.080
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 0.213 0.836 0.700 38 5 ' '
2 0.247 0.662 0.160 46 8 ' '
3 0.286 0.164 0.200 38 5 ' '
4 0.252 0.338 0.660 46 8 ' '
5 0.713 0.664 0.300 38 5 ' '
6 0.747 0.838 0.840 46 8 ' '
7 0.752 0.162 0.339 46 8 ' '
8 0.786 0.336 0.800 38 5 ' '
_platon_squeeze_details          
;
;
####################################################################### 
# 
# 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_bb
_database_code_depnum_ccdc_archive 'CCDC 1013686'
_audit_update_record             
;
2014-07-12 deposited with the CCDC.
2015-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H46 Cl2 Cu2 F12 N6 O0 P2'
_chemical_formula_weight         1194.83
_chemical_absolute_configuration s
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   14.258(3)
_cell_length_b                   15.075(3)
_cell_length_c                   23.007(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4945.1(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4048
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      27.9

_exptl_crystal_description       Prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2424
_exptl_absorpt_coefficient_mu    1.120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9847
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            40815
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         25.01
_reflns_number_total             8706
_reflns_number_gt                7989
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0621P)²+7.8689P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(10)
_refine_ls_number_reflns         8706
_refine_ls_number_parameters     651
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1214
_refine_ls_wR_factor_gt          0.1180
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.16287(3) 0.68323(3) 0.24591(2) 0.01627(13) Uani 1 1 d . . .
Cu2 Cu 0.33578(3) 0.85122(3) 0.24641(2) 0.01789(13) Uani 1 1 d . . .
N1 N 0.1478(3) 0.6899(3) 0.16180(15) 0.0176(8) Uani 1 1 d . . .
N2 N 0.0279(2) 0.7080(2) 0.24657(16) 0.0182(7) Uani 1 1 d . . .
N3 N 0.1469(3) 0.6790(3) 0.33117(15) 0.0206(8) Uani 1 1 d . . .
N4 N 0.3565(3) 0.8435(3) 0.16171(16) 0.0207(9) Uani 1 1 d . . .
N5 N 0.4706(2) 0.8395(2) 0.24967(16) 0.0198(7) Uani 1 1 d . . .
N6 N 0.3433(3) 0.8460(3) 0.33219(15) 0.0214(8) Uani 1 1 d . . .
Cl1 Cl 0.31012(6) 0.65474(6) 0.24658(5) 0.0201(2) Uani 1 1 d . . .
Cl2 Cl 0.19047(7) 0.88479(7) 0.24155(5) 0.0228(2) Uani 1 1 d . . .
C1 C 0.0432(3) 0.5053(3) 0.1799(2) 0.0268(11) Uani 1 1 d . . .
C2 C 0.1116(3) 0.4815(3) 0.2218(2) 0.0276(11) Uani 1 1 d . . .
H2 H 0.1091 0.5035 0.2595 0.033 Uiso 1 1 calc R . .
C3 C 0.1810(4) 0.4256(3) 0.2047(3) 0.0351(13) Uani 1 1 d . . .
H3 H 0.2262 0.4091 0.2318 0.042 Uiso 1 1 calc R . .
C4 C 0.1873(4) 0.3914(4) 0.1476(3) 0.0419(14) Uani 1 1 d . . .
H4 H 0.2376 0.3553 0.1374 0.050 Uiso 1 1 calc R . .
C5 C 0.1227(4) 0.4103(4) 0.1090(3) 0.0423(15) Uani 1 1 d . . .
H5 H 0.1261 0.3859 0.0719 0.051 Uiso 1 1 calc R . .
C6 C 0.0515(4) 0.4648(3) 0.1227(2) 0.0280(11) Uani 1 1 d . . .
C7 C -0.0204(4) 0.4834(4) 0.0825(3) 0.0403(14) Uani 1 1 d . . .
H7 H -0.0184 0.4586 0.0455 0.048 Uiso 1 1 calc R . .
C8 C -0.0911(4) 0.5363(4) 0.0972(3) 0.0395(13) Uani 1 1 d . . .
H8 H -0.1399 0.5455 0.0711 0.047 Uiso 1 1 calc R . .
C9 C -0.0933(4) 0.5790(4) 0.1523(2) 0.0348(13) Uani 1 1 d . . .
H9 H -0.1425 0.6177 0.1602 0.042 Uiso 1 1 calc R . .
C10 C -0.0281(3) 0.5663(3) 0.1933(2) 0.0263(11) Uani 1 1 d . . .
C11 C -0.0308(3) 0.6196(3) 0.2503(2) 0.0222(9) Uani 1 1 d . . .
H11 H -0.0019 0.5827 0.2804 0.027 Uiso 1 1 calc R . .
C12 C -0.1252(3) 0.6416(4) 0.2703(2) 0.0334(12) Uani 1 1 d . . .
H12A H -0.1492 0.6904 0.2479 0.050 Uiso 1 1 calc R . .
H12B H -0.1230 0.6580 0.3106 0.050 Uiso 1 1 calc R . .
H12C H -0.1654 0.5911 0.2655 0.050 Uiso 1 1 calc R . .
C13 C 0.2049(3) 0.6573(3) 0.12119(19) 0.0207(10) Uani 1 1 d . . .
H13 H 0.2593 0.6286 0.1331 0.025 Uiso 1 1 calc R . .
C14 C 0.1876(4) 0.6639(3) 0.0626(2) 0.0273(11) Uani 1 1 d . . .
H14 H 0.2289 0.6395 0.0357 0.033 Uiso 1 1 calc R . .
C15 C 0.1104(4) 0.7061(4) 0.0450(2) 0.0354(13) Uani 1 1 d . . .
H15 H 0.0974 0.7129 0.0057 0.042 Uiso 1 1 calc R . .
C16 C 0.0499(3) 0.7397(4) 0.0868(2) 0.0283(12) Uani 1 1 d . . .
H16 H -0.0045 0.7694 0.0758 0.034 Uiso 1 1 calc R . .
C17 C 0.0710(3) 0.7288(3) 0.1441(2) 0.0210(10) Uani 1 1 d . . .
C18 C 0.0108(3) 0.7625(3) 0.19274(19) 0.0198(10) Uani 1 1 d . . .
H18A H -0.0548 0.7588 0.1818 0.024 Uiso 1 1 calc R . .
H18B H 0.0255 0.8243 0.2004 0.024 Uiso 1 1 calc R . .
C19 C 0.0187(3) 0.7645(3) 0.30026(18) 0.0215(10) Uani 1 1 d . . .
H19A H 0.0448 0.8229 0.2932 0.026 Uiso 1 1 calc R . .
H19B H -0.0469 0.7712 0.3105 0.026 Uiso 1 1 calc R . .
C20 C 0.0698(3) 0.7204(3) 0.34789(19) 0.0202(10) Uani 1 1 d . . .
C21 C 0.0449(4) 0.7215(4) 0.4058(2) 0.0328(12) Uani 1 1 d . . .
H21 H -0.0105 0.7493 0.4170 0.039 Uiso 1 1 calc R . .
C22 C 0.1006(4) 0.6822(4) 0.4469(2) 0.0356(13) Uani 1 1 d . . .
H22 H 0.0851 0.6847 0.4861 0.043 Uiso 1 1 calc R . .
C23 C 0.1777(4) 0.6403(4) 0.4290(2) 0.0339(13) Uani 1 1 d . . .
H23 H 0.2162 0.6113 0.4555 0.041 Uiso 1 1 calc R . .
C24 C 0.1992(4) 0.6405(3) 0.3712(2) 0.0262(11) Uani 1 1 d . . .
H24 H 0.2538 0.6119 0.3593 0.031 Uiso 1 1 calc R . .
C25 C 0.2791(4) 0.8706(4) 0.3710(2) 0.0325(13) Uani 1 1 d . . .
H25 H 0.2233 0.8956 0.3579 0.039 Uiso 1 1 calc R . .
C26 C 0.2926(4) 0.8602(4) 0.4297(2) 0.0386(14) Uani 1 1 d . . .
H26 H 0.2463 0.8790 0.4554 0.046 Uiso 1 1 calc R . .
C27 C 0.3697(4) 0.8241(4) 0.4501(2) 0.0418(15) Uani 1 1 d . . .
H27 H 0.3785 0.8155 0.4898 0.050 Uiso 1 1 calc R . .
C28 C 0.4370(4) 0.7995(4) 0.4103(2) 0.0352(13) Uani 1 1 d . . .
H28 H 0.4929 0.7740 0.4226 0.042 Uiso 1 1 calc R . .
C29 C 0.4203(4) 0.8134(4) 0.3519(2) 0.0261(11) Uani 1 1 d . . .
C30 C 0.4874(3) 0.7876(3) 0.3057(2) 0.0252(11) Uani 1 1 d . . .
H30A H 0.4812 0.7247 0.2979 0.030 Uiso 1 1 calc R . .
H30B H 0.5509 0.7984 0.3191 0.030 Uiso 1 1 calc R . .
C31 C 0.4949(3) 0.7814(3) 0.19922(19) 0.0219(10) Uani 1 1 d . . .
H31A H 0.4825 0.7199 0.2089 0.026 Uiso 1 1 calc R . .
H31B H 0.5611 0.7873 0.1901 0.026 Uiso 1 1 calc R . .
C32 C 0.4369(3) 0.8085(3) 0.14776(19) 0.0204(10) Uani 1 1 d . . .
C33 C 0.4621(4) 0.7947(4) 0.0914(2) 0.0325(13) Uani 1 1 d . . .
H33 H 0.5196 0.7685 0.0831 0.039 Uiso 1 1 calc R . .
C34 C 0.4041(4) 0.8188(4) 0.0470(2) 0.0364(13) Uani 1 1 d . . .
H34 H 0.4209 0.8100 0.0084 0.044 Uiso 1 1 calc R . .
C35 C 0.3221(4) 0.8556(4) 0.0614(2) 0.0339(13) Uani 1 1 d . . .
H35 H 0.2802 0.8734 0.0327 0.041 Uiso 1 1 calc R . .
C36 C 0.3006(3) 0.8666(3) 0.1186(2) 0.0257(11) Uani 1 1 d . . .
H36 H 0.2430 0.8919 0.1279 0.031 Uiso 1 1 calc R . .
C37 C 0.5307(3) 0.9779(3) 0.1906(2) 0.0276(11) Uani 1 1 d . . .
H37A H 0.4695 0.9865 0.1742 0.041 Uiso 1 1 calc R . .
H37B H 0.5671 0.9406 0.1655 0.041 Uiso 1 1 calc R . .
H37C H 0.5613 1.0342 0.1949 0.041 Uiso 1 1 calc R . .
C38 C 0.5213(3) 0.9336(3) 0.2505(2) 0.0216(9) Uani 1 1 d . . .
H38 H 0.5851 0.9236 0.2649 0.026 Uiso 1 1 calc R . .
C39 C 0.4741(3) 1.0001(3) 0.2931(2) 0.0208(10) Uani 1 1 d . . .
C40 C 0.3975(3) 1.0446(3) 0.2753(2) 0.0250(10) Uani 1 1 d . . .
H40 H 0.3785 1.0405 0.2367 0.030 Uiso 1 1 calc R . .
C41 C 0.3459(3) 1.0972(3) 0.3140(2) 0.0271(11) Uani 1 1 d . . .
H41 H 0.2948 1.1290 0.3001 0.033 Uiso 1 1 calc R . .
C42 C 0.3677(4) 1.1032(3) 0.3701(2) 0.0313(12) Uani 1 1 d . . .
H42 H 0.3292 1.1351 0.3951 0.038 Uiso 1 1 calc R . .
C43 C 0.4475(4) 1.0620(3) 0.3913(2) 0.0255(10) Uani 1 1 d . . .
C44 C 0.5033(3) 1.0128(3) 0.3510(2) 0.0241(10) Uani 1 1 d . . .
C45 C 0.5862(4) 0.9790(4) 0.3733(2) 0.0312(12) Uani 1 1 d . . .
H45 H 0.6266 0.9478 0.3491 0.037 Uiso 1 1 calc R . .
C46 C 0.6091(4) 0.9910(4) 0.4299(2) 0.0379(13) Uani 1 1 d . . .
H46 H 0.6656 0.9677 0.4432 0.046 Uiso 1 1 calc R . .
C47 C 0.5523(5) 1.0363(4) 0.4693(2) 0.0429(15) Uani 1 1 d . . .
H47 H 0.5699 1.0418 0.5081 0.051 Uiso 1 1 calc R . .
C48 C 0.4737(4) 1.0710(4) 0.4505(2) 0.0387(13) Uani 1 1 d . . .
H48 H 0.4349 1.1016 0.4761 0.046 Uiso 1 1 calc R . .
F1 F 0.2157(3) 0.1719(3) 0.08899(18) 0.0795(13) Uani 1 1 d . . .
F2 F 0.2932(4) 0.0634(3) 0.1384(2) 0.0831(14) Uani 1 1 d U . .
F3 F 0.3286(5) 0.0945(4) 0.04464(19) 0.115(2) Uani 1 1 d . . .
F4 F 0.4220(3) 0.1331(3) 0.1151(2) 0.0767(13) Uani 1 1 d . . .
F5 F 0.3419(3) 0.2467(3) 0.0724(2) 0.0883(16) Uani 1 1 d . . .
F6 F 0.3111(3) 0.2096(3) 0.16150(18) 0.0761(13) Uani 1 1 d . . .
F7 F 0.1284(3) 0.3944(3) 0.3784(2) 0.0778(14) Uani 1 1 d . . .
F8 F 0.2348(3) 0.4315(3) 0.44093(17) 0.0705(12) Uani 1 1 d . . .
F9 F 0.2605(3) 0.4354(3) 0.34604(18) 0.0756(13) Uani 1 1 d . . .
F10 F 0.3245(3) 0.3265(3) 0.40231(18) 0.0647(11) Uani 1 1 d . . .
F11 F 0.2201(3) 0.2882(3) 0.33770(15) 0.0625(11) Uani 1 1 d . . .
F12 F 0.1916(3) 0.2776(3) 0.43231(18) 0.0728(12) Uani 1 1 d . . .
P1 P 0.31765(12) 0.15217(11) 0.10023(7) 0.0461(4) Uani 1 1 d U . .
P2 P 0.22670(9) 0.35335(11) 0.39079(6) 0.0330(3) Uani 1 1 d . . .


_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 1.950(4) . ?
Cu1 N2 1.961(3) . ?
Cu1 N3 1.976(4) . ?
Cu1 Cl1 2.1431(11) . ?
Cu2 N5 1.931(3) . ?
Cu2 N4 1.974(4) . ?
Cu2 N6 1.978(4) . ?
Cu2 Cl2 2.1358(12) . ?
N1 C17 1.307(6) . ?
N1 C13 1.333(6) . ?
N2 C19 1.506(6) . ?
N2 C18 1.506(6) . ?
N2 C11 1.576(5) . ?
N3 C24 1.320(6) . ?
N3 C20 1.321(6) . ?
N4 C32 1.301(6) . ?
N4 C36 1.319(6) . ?
N5 C31 1.495(6) . ?
N5 C30 1.527(6) . ?
N5 C38 1.592(5) . ?
N6 C29 1.286(7) . ?
N6 C25 1.331(6) . ?
C1 C10 1.405(7) . ?
C1 C2 1.416(7) . ?
C1 C6 1.456(7) . ?
C2 C3 1.358(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.415(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.311(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.343(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.409(8) . ?
C7 C8 1.328(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.422(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.339(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.538(7) . ?
C11 C12 1.460(6) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.375(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.334(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.387(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.363(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.500(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.474(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.378(7) . ?
C21 C22 1.371(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.333(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.366(7) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.373(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.314(8) . ?
C26 H26 0.9300 . ?
C27 C28 1.376(8) . ?
C27 H27 0.9300 . ?
C28 C29 1.380(7) . ?
C28 H28 0.9300 . ?
C29 C30 1.482(7) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.502(6) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.362(7) . ?
C33 C34 1.364(8) . ?
C33 H33 0.9300 . ?
C34 C35 1.335(8) . ?
C34 H34 0.9300 . ?
C35 C36 1.362(7) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 C38 1.536(7) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 C39 1.555(6) . ?
C38 H38 0.9800 . ?
C39 C40 1.346(6) . ?
C39 C44 1.410(7) . ?
C40 C41 1.401(7) . ?
C40 H40 0.9300 . ?
C41 C42 1.330(7) . ?
C41 H41 0.9300 . ?
C42 C43 1.385(7) . ?
C42 H42 0.9300 . ?
C43 C48 1.418(7) . ?
C43 C44 1.430(7) . ?
C44 C45 1.385(7) . ?
C45 C46 1.355(7) . ?
C45 H45 0.9300 . ?
C46 C47 1.394(8) . ?
C46 H46 0.9300 . ?
C47 C48 1.311(8) . ?
C47 H47 0.9300 . ?
C48 H48 0.9300 . ?
F1 P1 1.506(5) . ?
F2 P1 1.637(5) . ?
F3 P1 1.555(5) . ?
F4 P1 1.554(5) . ?
F5 P1 1.601(4) . ?
F6 P1 1.657(4) . ?
F7 P2 1.558(4) . ?
F8 P2 1.653(4) . ?
F9 P2 1.680(4) . ?
F10 P2 1.477(4) . ?
F11 P2 1.570(4) . ?
F12 P2 1.570(4) . ?

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 83.66(15) . . ?
N1 Cu1 N3 166.98(14) . . ?
N2 Cu1 N3 83.39(16) . . ?
N1 Cu1 Cl1 97.21(12) . . ?
N2 Cu1 Cl1 178.97(12) . . ?
N3 Cu1 Cl1 95.72(12) . . ?
N5 Cu2 N4 83.33(16) . . ?
N5 Cu2 N6 84.48(16) . . ?
N4 Cu2 N6 166.98(15) . . ?
N5 Cu2 Cl2 171.52(11) . . ?
N4 Cu2 Cl2 96.18(12) . . ?
N6 Cu2 Cl2 96.55(12) . . ?
C17 N1 C13 117.3(4) . . ?
C17 N1 Cu1 115.1(3) . . ?
C13 N1 Cu1 127.5(3) . . ?
C19 N2 C18 110.6(3) . . ?
C19 N2 C11 112.8(3) . . ?
C18 N2 C11 114.8(3) . . ?
C19 N2 Cu1 101.5(3) . . ?
C18 N2 Cu1 104.9(2) . . ?
C11 N2 Cu1 111.1(2) . . ?
C24 N3 C20 118.4(4) . . ?
C24 N3 Cu1 129.8(3) . . ?
C20 N3 Cu1 111.7(3) . . ?
C32 N4 C36 117.0(4) . . ?
C32 N4 Cu2 113.5(3) . . ?
C36 N4 Cu2 129.4(3) . . ?
C31 N5 C30 108.6(3) . . ?
C31 N5 C38 115.2(3) . . ?
C30 N5 C38 112.0(3) . . ?
C31 N5 Cu2 104.8(3) . . ?
C30 N5 Cu2 103.7(3) . . ?
C38 N5 Cu2 111.8(2) . . ?
C29 N6 C25 117.2(4) . . ?
C29 N6 Cu2 114.4(3) . . ?
C25 N6 Cu2 128.4(4) . . ?
C10 C1 C2 121.0(5) . . ?
C10 C1 C6 122.1(5) . . ?
C2 C1 C6 116.9(5) . . ?
C3 C2 C1 117.6(5) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 122.7(5) . . ?
C2 C3 H3 118.6 . . ?
C4 C3 H3 118.6 . . ?
C5 C4 C3 120.3(6) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.3(6) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C7 121.2(5) . . ?
C5 C6 C1 122.0(5) . . ?
C7 C6 C1 116.8(5) . . ?
C8 C7 C6 120.3(5) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 121.0(5) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C8 123.2(5) . . ?
C10 C9 H9 118.4 . . ?
C8 C9 H9 118.4 . . ?
C9 C10 C1 116.3(5) . . ?
C9 C10 C11 120.5(5) . . ?
C1 C10 C11 123.2(4) . . ?
C12 C11 C10 114.3(4) . . ?
C12 C11 N2 108.3(4) . . ?
C10 C11 N2 112.5(4) . . ?
C12 C11 H11 107.1 . . ?
C10 C11 H11 107.1 . . ?
N2 C11 H11 107.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 123.5(5) . . ?
N1 C13 H13 118.3 . . ?
C14 C13 H13 118.3 . . ?
C15 C14 C13 118.6(5) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C16 118.6(5) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C17 C16 C15 119.2(5) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
N1 C17 C16 122.7(5) . . ?
N1 C17 C18 113.6(4) . . ?
C16 C17 C18 123.7(4) . . ?
C17 C18 N2 109.6(4) . . ?
C17 C18 H18A 109.8 . . ?
N2 C18 H18A 109.8 . . ?
C17 C18 H18B 109.8 . . ?
N2 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
C20 C19 N2 108.2(4) . . ?
C20 C19 H19A 110.1 . . ?
N2 C19 H19A 110.1 . . ?
C20 C19 H19B 110.1 . . ?
N2 C19 H19B 110.1 . . ?
H19A C19 H19B 108.4 . . ?
N3 C20 C21 120.1(5) . . ?
N3 C20 C19 114.1(4) . . ?
C21 C20 C19 125.8(5) . . ?
C22 C21 C20 120.8(5) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 118.0(5) . . ?
C23 C22 H22 121.0 . . ?
C21 C22 H22 121.0 . . ?
C22 C23 C24 119.0(5) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
N3 C24 C23 123.6(5) . . ?
N3 C24 H24 118.2 . . ?
C23 C24 H24 118.2 . . ?
N6 C25 C26 122.1(6) . . ?
N6 C25 H25 118.9 . . ?
C26 C25 H25 118.9 . . ?
C27 C26 C25 121.0(6) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 C28 117.2(5) . . ?
C26 C27 H27 121.4 . . ?
C28 C27 H27 121.4 . . ?
C27 C28 C29 119.1(6) . . ?
C27 C28 H28 120.4 . . ?
C29 C28 H28 120.4 . . ?
N6 C29 C28 123.3(5) . . ?
N6 C29 C30 113.5(4) . . ?
C28 C29 C30 123.2(5) . . ?
C29 C30 N5 111.7(4) . . ?
C29 C30 H30A 109.3 . . ?
N5 C30 H30A 109.3 . . ?
C29 C30 H30B 109.3 . . ?
N5 C30 H30B 109.3 . . ?
H30A C30 H30B 107.9 . . ?
N5 C31 C32 108.9(4) . . ?
N5 C31 H31A 109.9 . . ?
C32 C31 H31A 109.9 . . ?
N5 C31 H31B 109.9 . . ?
C32 C31 H31B 109.9 . . ?
H31A C31 H31B 108.3 . . ?
N4 C32 C33 122.0(5) . . ?
N4 C32 C31 113.7(4) . . ?
C33 C32 C31 124.3(5) . . ?
C32 C33 C34 120.8(5) . . ?
C32 C33 H33 119.6 . . ?
C34 C33 H33 119.6 . . ?
C35 C34 C33 117.1(5) . . ?
C35 C34 H34 121.4 . . ?
C33 C34 H34 121.4 . . ?
C34 C35 C36 119.2(5) . . ?
C34 C35 H35 120.4 . . ?
C36 C35 H35 120.4 . . ?
N4 C36 C35 123.9(5) . . ?
N4 C36 H36 118.0 . . ?
C35 C36 H36 118.0 . . ?
C38 C37 H37A 109.5 . . ?
C38 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C38 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C37 C38 C39 108.8(4) . . ?
C37 C38 N5 114.6(4) . . ?
C39 C38 N5 112.7(3) . . ?
C37 C38 H38 106.8 . . ?
C39 C38 H38 106.8 . . ?
N5 C38 H38 106.8 . . ?
C40 C39 C44 117.4(4) . . ?
C40 C39 C38 118.8(4) . . ?
C44 C39 C38 123.8(4) . . ?
C39 C40 C41 121.0(5) . . ?
C39 C40 H40 119.5 . . ?
C41 C40 H40 119.5 . . ?
C42 C41 C40 122.2(5) . . ?
C42 C41 H41 118.9 . . ?
C40 C41 H41 118.9 . . ?
C41 C42 C43 120.3(5) . . ?
C41 C42 H42 119.9 . . ?
C43 C42 H42 119.9 . . ?
C42 C43 C48 120.9(5) . . ?
C42 C43 C44 117.4(4) . . ?
C48 C43 C44 121.7(5) . . ?
C45 C44 C39 123.5(5) . . ?
C45 C44 C43 115.2(5) . . ?
C39 C44 C43 121.3(4) . . ?
C46 C45 C44 120.8(5) . . ?
C46 C45 H45 119.6 . . ?
C44 C45 H45 119.6 . . ?
C45 C46 C47 123.4(5) . . ?
C45 C46 H46 118.3 . . ?
C47 C46 H46 118.3 . . ?
C48 C47 C46 118.5(5) . . ?
C48 C47 H47 120.7 . . ?
C46 C47 H47 120.7 . . ?
C47 C48 C43 120.3(5) . . ?
C47 C48 H48 119.9 . . ?
C43 C48 H48 119.9 . . ?
F1 P1 F4 177.1(3) . . ?
F1 P1 F3 93.8(3) . . ?
F4 P1 F3 88.9(3) . . ?
F1 P1 F5 87.9(3) . . ?
F4 P1 F5 92.6(3) . . ?
F3 P1 F5 98.4(3) . . ?
F1 P1 F2 92.7(3) . . ?
F4 P1 F2 86.3(3) . . ?
F3 P1 F2 90.3(3) . . ?
F5 P1 F2 171.2(3) . . ?
F1 P1 F6 89.3(2) . . ?
F4 P1 F6 87.9(2) . . ?
F3 P1 F6 176.3(3) . . ?
F5 P1 F6 83.6(3) . . ?
F2 P1 F6 87.6(3) . . ?
F10 P2 F7 172.5(3) . . ?
F10 P2 F11 91.4(2) . . ?
F7 P2 F11 93.0(2) . . ?
F10 P2 F12 89.6(3) . . ?
F7 P2 F12 96.5(3) . . ?
F11 P2 F12 90.0(2) . . ?
F10 P2 F8 90.2(2) . . ?
F7 P2 F8 84.7(2) . . ?
F11 P2 F8 173.2(2) . . ?
F12 P2 F8 96.7(2) . . ?
F10 P2 F9 92.3(2) . . ?
F7 P2 F9 81.6(3) . . ?
F11 P2 F9 90.1(2) . . ?
F12 P2 F9 178.1(3) . . ?
F8 P2 F9 83.3(2) . . ?

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
N2 Cu1 N1 C17 17.4(3) . . . . ?
N3 Cu1 N1 C17 23.6(8) . . . . ?
Cl1 Cu1 N1 C17 -163.1(3) . . . . ?
N2 Cu1 N1 C13 -160.5(4) . . . . ?
N3 Cu1 N1 C13 -154.3(6) . . . . ?
Cl1 Cu1 N1 C13 19.0(4) . . . . ?
N1 Cu1 N2 C19 -145.0(3) . . . . ?
N3 Cu1 N2 C19 36.4(3) . . . . ?
Cl1 Cu1 N2 C19 67(7) . . . . ?
N1 Cu1 N2 C18 -29.8(3) . . . . ?
N3 Cu1 N2 C18 151.6(3) . . . . ?
Cl1 Cu1 N2 C18 -178(100) . . . . ?
N1 Cu1 N2 C11 94.8(3) . . . . ?
N3 Cu1 N2 C11 -83.8(3) . . . . ?
Cl1 Cu1 N2 C11 -53(7) . . . . ?
N1 Cu1 N3 C24 152.0(6) . . . . ?
N2 Cu1 N3 C24 158.1(5) . . . . ?
Cl1 Cu1 N3 C24 -21.4(5) . . . . ?
N1 Cu1 N3 C20 -26.3(8) . . . . ?
N2 Cu1 N3 C20 -20.2(3) . . . . ?
Cl1 Cu1 N3 C20 160.4(3) . . . . ?
N5 Cu2 N4 C32 19.7(3) . . . . ?
N6 Cu2 N4 C32 -1.0(8) . . . . ?
Cl2 Cu2 N4 C32 -168.8(3) . . . . ?
N5 Cu2 N4 C36 -161.9(5) . . . . ?
N6 Cu2 N4 C36 177.4(6) . . . . ?
Cl2 Cu2 N4 C36 9.6(4) . . . . ?
N4 Cu2 N5 C31 -32.9(3) . . . . ?
N6 Cu2 N5 C31 142.5(3) . . . . ?
Cl2 Cu2 N5 C31 -120.1(8) . . . . ?
N4 Cu2 N5 C30 -146.7(3) . . . . ?
N6 Cu2 N5 C30 28.7(3) . . . . ?
Cl2 Cu2 N5 C30 126.1(7) . . . . ?
N4 Cu2 N5 C38 92.5(3) . . . . ?
N6 Cu2 N5 C38 -92.1(3) . . . . ?
Cl2 Cu2 N5 C38 5.3(10) . . . . ?
N5 Cu2 N6 C29 -18.7(4) . . . . ?
N4 Cu2 N6 C29 2.0(8) . . . . ?
Cl2 Cu2 N6 C29 169.8(4) . . . . ?
N5 Cu2 N6 C25 162.3(5) . . . . ?
N4 Cu2 N6 C25 -177.0(6) . . . . ?
Cl2 Cu2 N6 C25 -9.2(4) . . . . ?
C10 C1 C2 C3 -176.8(4) . . . . ?
C6 C1 C2 C3 2.3(6) . . . . ?
C1 C2 C3 C4 0.4(7) . . . . ?
C2 C3 C4 C5 -2.8(8) . . . . ?
C3 C4 C5 C6 2.2(9) . . . . ?
C4 C5 C6 C7 -177.7(5) . . . . ?
C4 C5 C6 C1 0.6(8) . . . . ?
C10 C1 C6 C5 176.2(5) . . . . ?
C2 C1 C6 C5 -2.9(7) . . . . ?
C10 C1 C6 C7 -5.4(7) . . . . ?
C2 C1 C6 C7 175.5(4) . . . . ?
C5 C6 C7 C8 178.9(5) . . . . ?
C1 C6 C7 C8 0.5(7) . . . . ?
C6 C7 C8 C9 3.6(8) . . . . ?
C7 C8 C9 C10 -3.0(8) . . . . ?
C8 C9 C10 C1 -1.8(7) . . . . ?
C8 C9 C10 C11 175.6(4) . . . . ?
C2 C1 C10 C9 -175.0(4) . . . . ?
C6 C1 C10 C9 5.9(7) . . . . ?
C2 C1 C10 C11 7.6(7) . . . . ?
C6 C1 C10 C11 -171.4(4) . . . . ?
C9 C10 C11 C12 32.9(7) . . . . ?
C1 C10 C11 C12 -149.8(5) . . . . ?
C9 C10 C11 N2 -91.1(5) . . . . ?
C1 C10 C11 N2 86.1(5) . . . . ?
C19 N2 C11 C12 47.7(5) . . . . ?
C18 N2 C11 C12 -80.3(5) . . . . ?
Cu1 N2 C11 C12 160.9(3) . . . . ?
C19 N2 C11 C10 175.0(4) . . . . ?
C18 N2 C11 C10 47.0(5) . . . . ?
Cu1 N2 C11 C10 -71.8(4) . . . . ?
C17 N1 C13 C14 1.0(7) . . . . ?
Cu1 N1 C13 C14 178.9(4) . . . . ?
N1 C13 C14 C15 0.9(8) . . . . ?
C13 C14 C15 C16 -1.4(8) . . . . ?
C14 C15 C16 C17 0.0(8) . . . . ?
C13 N1 C17 C16 -2.5(7) . . . . ?
Cu1 N1 C17 C16 179.4(4) . . . . ?
C13 N1 C17 C18 179.5(4) . . . . ?
Cu1 N1 C17 C18 1.4(5) . . . . ?
C15 C16 C17 N1 2.0(8) . . . . ?
C15 C16 C17 C18 179.9(5) . . . . ?
N1 C17 C18 N2 -26.8(5) . . . . ?
C16 C17 C18 N2 155.2(5) . . . . ?
C19 N2 C18 C17 146.5(4) . . . . ?
C11 N2 C18 C17 -84.4(4) . . . . ?
Cu1 N2 C18 C17 37.9(4) . . . . ?
C18 N2 C19 C20 -158.5(4) . . . . ?
C11 N2 C19 C20 71.4(4) . . . . ?
Cu1 N2 C19 C20 -47.6(4) . . . . ?
C24 N3 C20 C21 -1.0(7) . . . . ?
Cu1 N3 C20 C21 177.5(4) . . . . ?
C24 N3 C20 C19 177.5(4) . . . . ?
Cu1 N3 C20 C19 -4.0(5) . . . . ?
N2 C19 C20 N3 35.6(5) . . . . ?
N2 C19 C20 C21 -146.0(5) . . . . ?
N3 C20 C21 C22 1.9(8) . . . . ?
C19 C20 C21 C22 -176.4(5) . . . . ?
C20 C21 C22 C23 -2.4(9) . . . . ?
C21 C22 C23 C24 1.9(9) . . . . ?
C20 N3 C24 C23 0.7(8) . . . . ?
Cu1 N3 C24 C23 -177.5(4) . . . . ?
C22 C23 C24 N3 -1.1(9) . . . . ?
C29 N6 C25 C26 -1.4(8) . . . . ?
Cu2 N6 C25 C26 177.6(4) . . . . ?
N6 C25 C26 C27 -0.9(9) . . . . ?
C25 C26 C27 C28 1.7(9) . . . . ?
C26 C27 C28 C29 -0.3(9) . . . . ?
C25 N6 C29 C28 2.8(8) . . . . ?
Cu2 N6 C29 C28 -176.3(4) . . . . ?
C25 N6 C29 C30 179.8(4) . . . . ?
Cu2 N6 C29 C30 0.7(6) . . . . ?
C27 C28 C29 N6 -2.1(9) . . . . ?
C27 C28 C29 C30 -178.7(5) . . . . ?
N6 C29 C30 N5 24.5(6) . . . . ?
C28 C29 C30 N5 -158.6(5) . . . . ?
C31 N5 C30 C29 -147.5(4) . . . . ?
C38 N5 C30 C29 84.2(4) . . . . ?
Cu2 N5 C30 C29 -36.5(4) . . . . ?
C30 N5 C31 C32 151.6(4) . . . . ?
C38 N5 C31 C32 -81.9(4) . . . . ?
Cu2 N5 C31 C32 41.3(4) . . . . ?
C36 N4 C32 C33 -1.1(7) . . . . ?
Cu2 N4 C32 C33 177.5(4) . . . . ?
C36 N4 C32 C31 -178.1(4) . . . . ?
Cu2 N4 C32 C31 0.5(5) . . . . ?
N5 C31 C32 N4 -28.2(6) . . . . ?
N5 C31 C32 C33 154.9(5) . . . . ?
N4 C32 C33 C34 1.2(8) . . . . ?
C31 C32 C33 C34 177.9(5) . . . . ?
C32 C33 C34 C35 -0.5(9) . . . . ?
C33 C34 C35 C36 -0.3(9) . . . . ?
C32 N4 C36 C35 0.3(8) . . . . ?
Cu2 N4 C36 C35 -178.1(4) . . . . ?
C34 C35 C36 N4 0.4(9) . . . . ?
C31 N5 C38 C37 39.1(5) . . . . ?
C30 N5 C38 C37 163.9(4) . . . . ?
Cu2 N5 C38 C37 -80.3(4) . . . . ?
C31 N5 C38 C39 164.2(4) . . . . ?
C30 N5 C38 C39 -71.0(4) . . . . ?
Cu2 N5 C38 C39 44.8(4) . . . . ?
C37 C38 C39 C40 46.2(5) . . . . ?
N5 C38 C39 C40 -82.0(5) . . . . ?
C37 C38 C39 C44 -137.9(5) . . . . ?
N5 C38 C39 C44 93.9(5) . . . . ?
C44 C39 C40 C41 -3.8(7) . . . . ?
C38 C39 C40 C41 172.4(4) . . . . ?
C39 C40 C41 C42 -2.5(8) . . . . ?
C40 C41 C42 C43 4.9(8) . . . . ?
C41 C42 C43 C48 177.3(5) . . . . ?
C41 C42 C43 C44 -0.9(7) . . . . ?
C40 C39 C44 C45 -172.7(5) . . . . ?
C38 C39 C44 C45 11.3(7) . . . . ?
C40 C39 C44 C43 7.7(7) . . . . ?
C38 C39 C44 C43 -168.3(4) . . . . ?
C42 C43 C44 C45 174.9(5) . . . . ?
C48 C43 C44 C45 -3.3(7) . . . . ?
C42 C43 C44 C39 -5.4(7) . . . . ?
C48 C43 C44 C39 176.4(5) . . . . ?
C39 C44 C45 C46 -177.8(5) . . . . ?
C43 C44 C45 C46 1.9(7) . . . . ?
C44 C45 C46 C47 0.5(9) . . . . ?
C45 C46 C47 C48 -1.6(9) . . . . ?
C46 C47 C48 C43 0.1(9) . . . . ?
C42 C43 C48 C47 -175.8(6) . . . . ?
C44 C43 C48 C47 2.4(9) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.082
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 0.084 0.001 0.091 47 10 ' '
2 -0.084 0.501 0.409 47 10 ' '
3 0.080 0.459 0.951 37 6 ' '
4 0.416 -0.001 0.591 47 10 ' '
5 0.419 0.541 0.451 37 6 ' '
6 0.584 0.499 0.909 47 10 ' '
7 0.580 0.041 0.049 37 6 ' '
8 0.920 0.959 0.549 37 6 ' '
_platon_squeeze_details          
;
;
####################################################################### 
# 
# 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_0430-ysp-zhou-1
_database_code_depnum_ccdc_archive 'CCDC 1013687'
_audit_update_record             
;
2014-07-12 deposited with the CCDC.
2015-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H30 Cu F6 N3 O2 P'
_chemical_formula_weight         661.07
_chemical_absolute_configuration R
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'
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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           Orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   12.0797(2)
_cell_length_b                   14.2249(3)
_cell_length_c                   17.4935(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3005.95(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4313
_cell_measurement_theta_min      3.2059
_cell_measurement_theta_max      28.3573

_exptl_crystal_description       Prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1356
_exptl_absorpt_coefficient_mu    0.848
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7880
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4809
_reflns_number_gt                4445
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0931P)²+2.3948P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.014(16)
_refine_ls_number_reflns         4809
_refine_ls_number_parameters     382
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1129
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   0.760
_refine_ls_restrained_S_all      0.760
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.002

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 0.38531(3) 0.84888(3) 0.80666(2) 0.04873(14) Uani 1 1 d . . .
N1 N 0.3296(3) 0.9748(2) 0.77569(17) 0.0476(7) Uani 1 1 d . . .
N2 N 0.2239(3) 0.8063(2) 0.77729(18) 0.0486(7) Uani 1 1 d . . .
N3 N 0.4084(3) 0.7907(2) 0.6896(2) 0.0601(8) Uani 1 1 d . . .
O1 O 0.5259(2) 0.89651(19) 0.84237(16) 0.0582(6) Uani 1 1 d . . .
O2 O 0.4079(2) 0.72709(19) 0.85192(18) 0.0666(8) Uani 1 1 d . . .
C6 C 0.4900(4) 0.8034(4) 0.6387(3) 0.0731(12) Uani 1 1 d . . .
H6 H 0.5430 0.8495 0.6477 0.088 Uiso 1 1 calc R . .
C7 C 0.4971(6) 0.7495(5) 0.5733(3) 0.0953(18) Uani 1 1 d . . .
H7 H 0.5555 0.7577 0.5392 0.114 Uiso 1 1 calc R . .
C8 C 0.4173(7) 0.6844(5) 0.5596(4) 0.115(3) Uani 1 1 d . . .
H8 H 0.4217 0.6466 0.5163 0.138 Uiso 1 1 calc R . .
C9 C 0.3315(5) 0.6742(4) 0.6085(3) 0.0893(17) Uani 1 1 d . . .
H9 H 0.2743 0.6326 0.5976 0.107 Uiso 1 1 calc R . .
C10 C 0.3305(4) 0.7275(3) 0.6757(2) 0.0627(11) Uani 1 1 d . . .
C11 C 0.2401(4) 0.7174(3) 0.7341(3) 0.0631(11) Uani 1 1 d . . .
H11A H 0.1716 0.7004 0.7088 0.076 Uiso 1 1 calc R . .
H11B H 0.2590 0.6673 0.7695 0.076 Uiso 1 1 calc R . .
C12 C 0.1807(3) 0.8805(2) 0.7250(2) 0.0488(8) Uani 1 1 d . . .
H12A H 0.1008 0.8841 0.7300 0.059 Uiso 1 1 calc R . .
H12B H 0.1975 0.8634 0.6725 0.059 Uiso 1 1 calc R . .
C13 C 0.2299(3) 0.9750(2) 0.74202(19) 0.0466(8) Uani 1 1 d . . .
C14 C 0.1781(4) 1.0575(3) 0.7220(3) 0.0613(10) Uani 1 1 d . . .
H14 H 0.1087 1.0565 0.6989 0.074 Uiso 1 1 calc R . .
C15 C 0.2304(4) 1.1412(3) 0.7365(3) 0.0777(13) Uani 1 1 d . . .
H15 H 0.1963 1.1976 0.7236 0.093 Uiso 1 1 calc R . .
C16 C 0.3323(4) 1.1417(3) 0.7699(3) 0.0798(13) Uani 1 1 d . . .
H16 H 0.3690 1.1980 0.7790 0.096 Uiso 1 1 calc R . .
C17 C 0.3798(4) 1.0570(3) 0.7898(2) 0.0627(10) Uani 1 1 d . . .
H17 H 0.4486 1.0570 0.8136 0.075 Uiso 1 1 calc R . .
C18 C 0.1509(3) 0.7917(3) 0.8469(3) 0.0597(10) Uani 1 1 d . . .
H18 H 0.1947 0.7562 0.8841 0.072 Uiso 1 1 calc R . .
C19 C 0.0464(4) 0.7332(4) 0.8300(4) 0.0879(16) Uani 1 1 d . . .
H19A H 0.0675 0.6705 0.8158 0.132 Uiso 1 1 calc R . .
H19B H 0.0058 0.7617 0.7889 0.132 Uiso 1 1 calc R . .
H19C H 0.0007 0.7309 0.8748 0.132 Uiso 1 1 calc R . .
C20 C 0.1238(4) 0.8865(3) 0.8836(2) 0.0599(9) Uani 1 1 d . . .
C21 C 0.0278(4) 0.9332(4) 0.8641(3) 0.0724(12) Uani 1 1 d . . .
H21 H -0.0250 0.9020 0.8349 0.087 Uiso 1 1 calc R . .
C22 C 0.0074(5) 1.0247(4) 0.8864(3) 0.0903(16) Uani 1 1 d . . .
H22 H -0.0594 1.0532 0.8737 0.108 Uiso 1 1 calc R . .
C23 C 0.0831(5) 1.0726(4) 0.9262(3) 0.0885(16) Uani 1 1 d . . .
H23 H 0.0709 1.1357 0.9371 0.106 Uiso 1 1 calc R . .
C24 C 0.1807(4) 1.0297(4) 0.9519(2) 0.0719(12) Uani 1 1 d . . .
C25 C 0.2588(6) 1.0771(5) 0.9974(3) 0.0924(17) Uani 1 1 d . . .
H25 H 0.2464 1.1398 1.0100 0.111 Uiso 1 1 calc R . .
C26 C 0.3520(5) 1.0341(5) 1.0237(3) 0.0963(19) Uani 1 1 d . . .
H26 H 0.4034 1.0673 1.0526 0.116 Uiso 1 1 calc R . .
C27 C 0.3693(4) 0.9395(5) 1.0066(2) 0.0847(15) Uani 1 1 d . . .
H27 H 0.4315 0.9095 1.0262 0.102 Uiso 1 1 calc R . .
C28 C 0.2974(4) 0.8894(4) 0.9619(2) 0.0665(11) Uani 1 1 d . . .
H28 H 0.3118 0.8266 0.9509 0.080 Uiso 1 1 calc R . .
C29 C 0.2003(3) 0.9333(3) 0.9321(2) 0.0603(10) Uani 1 1 d . . .
C4AA C 0.4936(4) 0.7008(3) 0.8883(2) 0.0654(11) Uani 1 1 d . . .
C1BA C 0.6986(4) 0.9039(4) 0.9039(4) 0.0861(15) Uani 1 1 d . . .
H1B1 H 0.6849 0.9400 0.9492 0.129 Uiso 1 1 calc R . .
H1B2 H 0.7197 0.9451 0.8630 0.129 Uiso 1 1 calc R . .
H1B3 H 0.7572 0.8598 0.9135 0.129 Uiso 1 1 calc R . .
C2BA C 0.5944(3) 0.8510(3) 0.8817(2) 0.0607(9) Uani 1 1 d . . .
C3CA C 0.5828(4) 0.7588(3) 0.9045(3) 0.0732(13) Uani 1 1 d . . .
H3CA H 0.6399 0.7331 0.9334 0.088 Uiso 1 1 calc R . .
C5DA C 0.4935(5) 0.5991(4) 0.9126(4) 0.099(2) Uani 1 1 d . . .
H5D1 H 0.4752 0.5601 0.8697 0.148 Uiso 1 1 calc R . .
H5D2 H 0.4397 0.5900 0.9524 0.148 Uiso 1 1 calc R . .
H5D3 H 0.5655 0.5823 0.9314 0.148 Uiso 1 1 calc R . .
F1 F 0.1452(8) 0.4929(6) 0.9106(4) 0.251(4) Uani 1 1 d . . .
F2 F 0.1105(5) 0.4907(3) 0.7863(3) 0.161(2) Uani 1 1 d . . .
F3 F 0.0737(4) 0.3666(5) 0.8631(3) 0.180(2) Uani 1 1 d . . .
F4 F 0.2015(7) 0.3622(3) 0.7785(3) 0.192(3) Uani 1 1 d . . .
F5 F 0.2440(4) 0.3697(5) 0.9023(3) 0.179(2) Uani 1 1 d . . .
F6 F 0.2794(5) 0.4878(5) 0.8246(5) 0.215(3) Uani 1 1 d . . .
P P 0.17776(11) 0.42891(10) 0.84500(8) 0.0735(3) Uani 1 1 d . . .


_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 O2 1.924(3) . ?
Cu1 O1 1.932(3) . ?
Cu1 N1 1.989(3) . ?
Cu1 N2 2.106(3) . ?
Cu1 N3 2.226(4) . ?
N1 C17 1.341(5) . ?
N1 C13 1.340(5) . ?
N2 C11 1.486(5) . ?
N2 C12 1.492(4) . ?
N2 C18 1.517(5) . ?
N3 C10 1.324(5) . ?
N3 C6 1.341(6) . ?
O1 C2BA 1.256(5) . ?
O2 C4AA 1.272(5) . ?
C6 C7 1.380(8) . ?
C7 C8 1.359(10) . ?
C8 C9 1.351(10) . ?
C9 C10 1.399(6) . ?
C10 C11 1.503(7) . ?
C12 C13 1.500(5) . ?
C13 C14 1.375(5) . ?
C14 C15 1.372(6) . ?
C15 C16 1.361(7) . ?
C16 C17 1.379(6) . ?
C18 C20 1.529(6) . ?
C18 C19 1.541(6) . ?
C20 C21 1.378(6) . ?
C20 C29 1.420(6) . ?
C21 C22 1.382(8) . ?
C22 C23 1.336(8) . ?
C23 C24 1.401(8) . ?
C24 C25 1.407(8) . ?
C24 C29 1.434(7) . ?
C25 C26 1.362(9) . ?
C26 C27 1.394(9) . ?
C27 C28 1.369(7) . ?
C28 C29 1.427(6) . ?
C4AA C3CA 1.386(7) . ?
C4AA C5DA 1.509(6) . ?
C1BA C2BA 1.517(6) . ?
C2BA C3CA 1.378(7) . ?
F1 P 1.517(5) . ?
F2 P 1.578(4) . ?
F3 P 1.570(5) . ?
F4 P 1.528(4) . ?
F5 P 1.534(4) . ?
F6 P 1.529(5) . ?

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
O2 Cu1 O1 93.34(12) . . ?
O2 Cu1 N1 166.15(13) . . ?
O1 Cu1 N1 94.01(12) . . ?
O2 Cu1 N2 88.43(12) . . ?
O1 Cu1 N2 173.59(12) . . ?
N1 Cu1 N2 83.05(12) . . ?
O2 Cu1 N3 91.50(13) . . ?
O1 Cu1 N3 108.52(12) . . ?
N1 Cu1 N3 97.26(12) . . ?
N2 Cu1 N3 77.56(12) . . ?
C17 N1 C13 119.0(3) . . ?
C17 N1 Cu1 125.6(3) . . ?
C13 N1 Cu1 115.2(2) . . ?
C11 N2 C12 109.7(3) . . ?
C11 N2 C18 111.6(3) . . ?
C12 N2 C18 112.7(3) . . ?
C11 N2 Cu1 104.3(2) . . ?
C12 N2 Cu1 105.7(2) . . ?
C18 N2 Cu1 112.4(2) . . ?
C10 N3 C6 119.5(4) . . ?
C10 N3 Cu1 109.4(3) . . ?
C6 N3 Cu1 130.8(3) . . ?
C2BA O1 Cu1 125.1(3) . . ?
C4AA O2 Cu1 125.8(3) . . ?
N3 C6 C7 121.4(6) . . ?
C8 C7 C6 118.7(6) . . ?
C9 C8 C7 120.4(5) . . ?
C8 C9 C10 118.7(6) . . ?
N3 C10 C9 121.1(5) . . ?
N3 C10 C11 117.1(4) . . ?
C9 C10 C11 121.8(5) . . ?
N2 C11 C10 111.1(3) . . ?
N2 C12 C13 111.9(3) . . ?
N1 C13 C14 121.5(3) . . ?
N1 C13 C12 116.2(3) . . ?
C14 C13 C12 122.2(3) . . ?
C15 C14 C13 118.9(4) . . ?
C16 C15 C14 120.0(4) . . ?
C15 C16 C17 118.7(4) . . ?
N1 C17 C16 121.8(4) . . ?
N2 C18 C20 109.9(3) . . ?
N2 C18 C19 113.3(4) . . ?
C20 C18 C19 112.4(4) . . ?
C21 C20 C29 118.0(4) . . ?
C21 C20 C18 120.1(4) . . ?
C29 C20 C18 121.6(4) . . ?
C20 C21 C22 122.3(5) . . ?
C23 C22 C21 120.4(5) . . ?
C22 C23 C24 121.4(5) . . ?
C25 C24 C23 122.4(6) . . ?
C25 C24 C29 119.0(5) . . ?
C23 C24 C29 118.5(5) . . ?
C26 C25 C24 122.0(6) . . ?
C25 C26 C27 119.1(5) . . ?
C28 C27 C26 122.0(6) . . ?
C27 C28 C29 120.1(5) . . ?
C20 C29 C28 123.2(4) . . ?
C20 C29 C24 119.0(4) . . ?
C28 C29 C24 117.8(4) . . ?
O2 C4AA C3CA 124.1(4) . . ?
O2 C4AA C5DA 115.0(4) . . ?
C3CA C4AA C5DA 120.9(4) . . ?
O1 C2BA C3CA 125.6(4) . . ?
O1 C2BA C1BA 115.6(4) . . ?
C3CA C2BA C1BA 118.8(4) . . ?
C2BA C3CA C4AA 125.9(4) . . ?
F1 P F4 175.7(5) . . ?
F1 P F6 93.2(5) . . ?
F4 P F6 90.6(4) . . ?
F1 P F5 88.3(4) . . ?
F4 P F5 93.3(3) . . ?
F6 P F5 92.0(3) . . ?
F1 P F3 88.8(5) . . ?
F4 P F3 87.3(4) . . ?
F6 P F3 177.9(4) . . ?
F5 P F3 88.6(3) . . ?
F1 P F2 91.4(4) . . ?
F4 P F2 87.0(3) . . ?
F6 P F2 87.5(3) . . ?
F5 P F2 179.4(4) . . ?
F3 P F2 91.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_aa
_database_code_depnum_ccdc_archive 'CCDC 1013688'
_audit_update_record             
;
2014-07-12 deposited with the CCDC.
2015-04-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H30 Cu F6 N3 O2 P'
_chemical_formula_weight         661.07
_chemical_absolute_configuration s
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   11.948(3)
_cell_length_b                   14.110(3)
_cell_length_c                   17.229(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2904.6(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    10284
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      28.1

_exptl_crystal_description       Prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1356
_exptl_absorpt_coefficient_mu    0.878
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.841
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   CrystalClear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(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  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22145
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0482
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         25.01
_reflns_number_total             5115
_reflns_number_gt                4891
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0626P)²+5.4731P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.038(13)
_refine_ls_number_reflns         5115
_refine_ls_number_parameters     382
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0936
_refine_ls_wR_factor_gt          0.0912
_refine_ls_goodness_of_fit_ref   0.738
_refine_ls_restrained_S_all      0.738
_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 0.38944(3) 0.15192(3) 0.80668(2) 0.02205(12) Uani 1 1 d . . .
N1 N 0.4148(2) 0.20988(19) 0.68741(18) 0.0264(7) Uani 1 1 d . . .
N2 N 0.2273(2) 0.19750(19) 0.77728(17) 0.0197(6) Uani 1 1 d . . .
N3 N 0.3320(2) 0.0256(2) 0.77483(16) 0.0219(6) Uani 1 1 d . . .
O1 O 0.4134(2) 0.27460(18) 0.85212(15) 0.0315(6) Uani 1 1 d . . .
O2 O 0.53061(19) 0.10188(17) 0.84236(15) 0.0276(6) Uani 1 1 d . . .
C1 C 0.7042(3) 0.0931(3) 0.9054(2) 0.0348(9) Uani 1 1 d . . .
H1A H 0.7322 0.0592 0.8611 0.052 Uiso 1 1 calc R . .
H1B H 0.6857 0.0490 0.9458 0.052 Uiso 1 1 calc R . .
H1C H 0.7604 0.1362 0.9237 0.052 Uiso 1 1 calc R . .
C2 C 0.6009(3) 0.1478(3) 0.88251(19) 0.0267(7) Uani 1 1 d . . .
C3 C 0.5913(3) 0.2417(3) 0.9058(2) 0.0332(9) Uani 1 1 d . . .
H3 H 0.6496 0.2671 0.9349 0.040 Uiso 1 1 calc R . .
C4 C 0.5015(3) 0.3003(3) 0.8889(2) 0.0317(9) Uani 1 1 d . . .
C5 C 0.5040(4) 0.4032(3) 0.9124(3) 0.0447(12) Uani 1 1 d . . .
H5A H 0.4617 0.4116 0.9593 0.067 Uiso 1 1 calc R . .
H5B H 0.4717 0.4411 0.8718 0.067 Uiso 1 1 calc R . .
H5C H 0.5800 0.4225 0.9209 0.067 Uiso 1 1 calc R . .
C6 C 0.4965(3) 0.1953(3) 0.6365(2) 0.0334(9) Uani 1 1 d . . .
H6 H 0.5494 0.1485 0.6462 0.040 Uiso 1 1 calc R . .
C7 C 0.5043(4) 0.2486(3) 0.5690(3) 0.0437(11) Uani 1 1 d . . .
H7 H 0.5631 0.2393 0.5344 0.052 Uiso 1 1 calc R . .
C8 C 0.4237(4) 0.3153(3) 0.5542(3) 0.0480(12) Uani 1 1 d . . .
H8 H 0.4281 0.3522 0.5096 0.058 Uiso 1 1 calc R . .
C9 C 0.3364(4) 0.3277(3) 0.6051(3) 0.0415(11) Uani 1 1 d . . .
H9 H 0.2796 0.3707 0.5942 0.050 Uiso 1 1 calc R . .
C10 C 0.3344(3) 0.2740(2) 0.6741(2) 0.0303(9) Uani 1 1 d . . .
C11 C 0.2445(3) 0.2859(3) 0.7339(2) 0.0303(9) Uani 1 1 d . . .
H11A H 0.2653 0.3361 0.7696 0.036 Uiso 1 1 calc R . .
H11B H 0.1752 0.3041 0.7087 0.036 Uiso 1 1 calc R . .
C12 C 0.1526(3) 0.2121(3) 0.8484(2) 0.0254(8) Uani 1 1 d . . .
H12 H 0.1966 0.2471 0.8869 0.030 Uiso 1 1 calc R . .
C13 C 0.0489(3) 0.2721(3) 0.8299(2) 0.0354(10) Uani 1 1 d . . .
H13A H -0.0011 0.2711 0.8735 0.053 Uiso 1 1 calc R . .
H13B H 0.0117 0.2465 0.7852 0.053 Uiso 1 1 calc R . .
H13C H 0.0713 0.3361 0.8195 0.053 Uiso 1 1 calc R . .
C14 C 0.1247(3) 0.1161(2) 0.8835(2) 0.0237(7) Uani 1 1 d . . .
C15 C 0.0260(3) 0.0713(3) 0.8637(2) 0.0282(8) Uani 1 1 d . . .
H15 H -0.0275 0.1045 0.8355 0.034 Uiso 1 1 calc R . .
C16 C 0.0041(3) -0.0229(3) 0.8847(2) 0.0344(9) Uani 1 1 d . . .
H16 H -0.0635 -0.0510 0.8709 0.041 Uiso 1 1 calc R . .
C17 C 0.0820(3) -0.0733(3) 0.9254(2) 0.0368(10) Uani 1 1 d . . .
H17 H 0.0695 -0.1371 0.9359 0.044 Uiso 1 1 calc R . .
C18 C 0.1808(3) -0.0298(3) 0.9517(2) 0.0293(8) Uani 1 1 d . . .
C19 C 0.2024(3) 0.0666(3) 0.9327(2) 0.0241(8) Uani 1 1 d . . .
C20 C 0.3016(3) 0.1088(3) 0.9630(2) 0.0266(8) Uani 1 1 d . . .
H20 H 0.3169 0.1721 0.9521 0.032 Uiso 1 1 calc R . .
C21 C 0.3743(3) 0.0584(3) 1.0074(2) 0.0333(9) Uani 1 1 d . . .
H21 H 0.4378 0.0878 1.0271 0.040 Uiso 1 1 calc R . .
C22 C 0.3547(3) -0.0375(3) 1.0239(2) 0.0372(10) Uani 1 1 d . . .
H22 H 0.4062 -0.0719 1.0531 0.045 Uiso 1 1 calc R . .
C23 C 0.2602(3) -0.0799(3) 0.9972(2) 0.0349(9) Uani 1 1 d . . .
H23 H 0.2472 -0.1432 1.0089 0.042 Uiso 1 1 calc R . .
C24 C 0.1825(3) 0.1236(2) 0.7233(2) 0.0209(7) Uani 1 1 d . . .
H24A H 0.2008 0.1407 0.6703 0.025 Uiso 1 1 calc R . .
H24B H 0.1017 0.1211 0.7279 0.025 Uiso 1 1 calc R . .
C25 C 0.2306(3) 0.0273(2) 0.7411(2) 0.0203(7) Uani 1 1 d . . .
C26 C 0.1762(3) -0.0555(2) 0.7203(2) 0.0260(8) Uani 1 1 d . . .
H26 H 0.1059 -0.0533 0.6972 0.031 Uiso 1 1 calc R . .
C27 C 0.2278(3) -0.1411(3) 0.7344(2) 0.0355(9) Uani 1 1 d . . .
H27 H 0.1930 -0.1976 0.7205 0.043 Uiso 1 1 calc R . .
C28 C 0.3312(3) -0.1418(3) 0.7691(2) 0.0334(9) Uani 1 1 d . . .
H28 H 0.3672 -0.1990 0.7790 0.040 Uiso 1 1 calc R . .
C29 C 0.3810(3) -0.0578(2) 0.7892(2) 0.0285(8) Uani 1 1 d . . .
H29 H 0.4507 -0.0589 0.8133 0.034 Uiso 1 1 calc R . .
F1 F 0.1316(4) 0.5107(3) 0.91384(19) 0.0982(13) Uani 1 1 d . . .
F2 F 0.1097(3) 0.51128(18) 0.78380(16) 0.0595(7) Uani 1 1 d . . .
F3 F 0.2814(3) 0.5076(3) 0.8334(2) 0.0884(12) Uani 1 1 d . . .
F4 F 0.2439(2) 0.6355(3) 0.90585(17) 0.0707(10) Uani 1 1 d . . .
F5 F 0.0714(2) 0.6427(2) 0.85692(17) 0.0667(8) Uani 1 1 d . . .
F6 F 0.2163(3) 0.6397(2) 0.77630(17) 0.0759(10) Uani 1 1 d . . .
P1 P 0.17788(9) 0.57381(8) 0.84500(7) 0.0359(3) Uani 1 1 d . . .


_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 1.921(3) . ?
Cu1 O2 1.929(2) . ?
Cu1 N3 1.987(3) . ?
Cu1 N2 2.103(3) . ?
Cu1 N1 2.232(3) . ?
N1 C6 1.329(5) . ?
N1 C10 1.339(5) . ?
N2 C11 1.468(4) . ?
N2 C24 1.496(4) . ?
N2 C12 1.529(4) . ?
N3 C29 1.338(4) . ?
N3 C25 1.344(4) . ?
O1 C4 1.281(4) . ?
O2 C2 1.267(4) . ?
C1 C2 1.508(5) . ?
C2 C3 1.388(5) . ?
C3 C4 1.386(5) . ?
C4 C5 1.508(5) . ?
C6 C7 1.388(6) . ?
C7 C8 1.370(7) . ?
C8 C9 1.373(7) . ?
C9 C10 1.410(5) . ?
C10 C11 1.498(5) . ?
C12 C14 1.522(5) . ?
C12 C13 1.533(5) . ?
C14 C15 1.381(5) . ?
C14 C19 1.437(5) . ?
C15 C16 1.402(5) . ?
C16 C17 1.365(6) . ?
C17 C18 1.406(6) . ?
C18 C23 1.418(5) . ?
C18 C19 1.424(5) . ?
C19 C20 1.426(5) . ?
C20 C21 1.359(5) . ?
C21 C22 1.401(6) . ?
C22 C23 1.359(6) . ?
C24 C25 1.506(4) . ?
C25 C26 1.384(5) . ?
C26 C27 1.378(5) . ?
C27 C28 1.373(5) . ?
C28 C29 1.370(5) . ?
F1 P1 1.583(3) . ?
F2 P1 1.598(3) . ?
F3 P1 1.562(3) . ?
F4 P1 1.574(3) . ?
F5 P1 1.614(3) . ?
F6 P1 1.574(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 93.99(10) . . ?
O1 Cu1 N3 166.43(12) . . ?
O2 Cu1 N3 93.54(11) . . ?
O1 Cu1 N2 87.70(10) . . ?
O2 Cu1 N2 173.75(11) . . ?
N3 Cu1 N2 83.66(11) . . ?
O1 Cu1 N1 91.42(11) . . ?
O2 Cu1 N1 107.99(10) . . ?
N3 Cu1 N1 96.97(11) . . ?
N2 Cu1 N1 77.96(11) . . ?
C6 N1 C10 121.2(3) . . ?
C6 N1 Cu1 130.6(3) . . ?
C10 N1 Cu1 107.9(2) . . ?
C11 N2 C24 109.1(3) . . ?
C11 N2 C12 112.0(3) . . ?
C24 N2 C12 112.5(3) . . ?
C11 N2 Cu1 104.7(2) . . ?
C24 N2 Cu1 105.40(19) . . ?
C12 N2 Cu1 112.7(2) . . ?
C29 N3 C25 119.4(3) . . ?
C29 N3 Cu1 125.9(2) . . ?
C25 N3 Cu1 114.5(2) . . ?
C4 O1 Cu1 125.4(2) . . ?
C2 O2 Cu1 124.5(2) . . ?
O2 C2 C3 126.3(3) . . ?
O2 C2 C1 115.0(3) . . ?
C3 C2 C1 118.7(3) . . ?
C4 C3 C2 124.9(3) . . ?
O1 C4 C3 124.8(3) . . ?
O1 C4 C5 114.9(3) . . ?
C3 C4 C5 120.2(4) . . ?
N1 C6 C7 121.3(4) . . ?
C8 C7 C6 118.7(4) . . ?
C7 C8 C9 120.2(4) . . ?
C8 C9 C10 118.8(4) . . ?
N1 C10 C9 119.7(4) . . ?
N1 C10 C11 118.2(3) . . ?
C9 C10 C11 122.1(4) . . ?
N2 C11 C10 110.8(3) . . ?
C14 C12 N2 109.1(3) . . ?
C14 C12 C13 113.4(3) . . ?
N2 C12 C13 112.3(3) . . ?
C15 C14 C19 118.4(3) . . ?
C15 C14 C12 119.7(3) . . ?
C19 C14 C12 121.7(3) . . ?
C14 C15 C16 122.0(4) . . ?
C17 C16 C15 120.0(4) . . ?
C16 C17 C18 120.7(4) . . ?
C17 C18 C23 121.5(4) . . ?
C17 C18 C19 119.7(4) . . ?
C23 C18 C19 118.8(4) . . ?
C18 C19 C20 117.7(3) . . ?
C18 C19 C14 118.9(3) . . ?
C20 C19 C14 123.4(3) . . ?
C21 C20 C19 121.2(4) . . ?
C20 C21 C22 120.9(4) . . ?
C23 C22 C21 119.6(4) . . ?
C22 C23 C18 121.6(4) . . ?
N2 C24 C25 111.5(3) . . ?
N3 C25 C26 121.3(3) . . ?
N3 C25 C24 116.6(3) . . ?
C26 C25 C24 122.0(3) . . ?
C27 C26 C25 119.0(3) . . ?
C28 C27 C26 119.0(4) . . ?
C29 C28 C27 119.7(4) . . ?
N3 C29 C28 121.6(3) . . ?
F3 P1 F6 91.5(2) . . ?
F3 P1 F4 91.10(17) . . ?
F6 P1 F4 91.61(18) . . ?
F3 P1 F1 92.1(2) . . ?
F6 P1 F1 176.3(2) . . ?
F4 P1 F1 89.3(2) . . ?
F3 P1 F2 89.38(18) . . ?
F6 P1 F2 88.79(16) . . ?
F4 P1 F2 179.37(18) . . ?
F1 P1 F2 90.31(18) . . ?
F3 P1 F5 179.7(2) . . ?
F6 P1 F5 88.26(19) . . ?
F4 P1 F5 88.68(16) . . ?
F1 P1 F5 88.2(2) . . ?
F2 P1 F5 90.84(16) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.053
