# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1053098'
_audit_update_record             
;
2015-03-10 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' C42 H36 Cu F N5 O4 P, N O3, 3(H2 O) '
_chemical_formula_sum            ' C42 H42 Cu F N6 O10 P '
_chemical_formula_weight         904.32

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.174(2)
_cell_length_b                   13.6130(10)
_cell_length_c                   14.4830(10)
_cell_angle_alpha                62.360(10)
_cell_angle_beta                 73.400(10)
_cell_angle_gamma                71.820(10)
_cell_volume                     1991.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5460
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      32.15

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_F_000             938
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.662
_shelx_estimated_absorpt_T_min   0.925
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.9248
_exptl_absorpt_correction_T_max  0.9614
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19259
_diffrn_reflns_av_unetI/netI     0.0856
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.956
_diffrn_reflns_theta_max         36.590
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.505
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.505
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.505
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             9938
_reflns_number_gt                6370
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1999)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0877P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9938
_refine_ls_number_parameters     550
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1576
_refine_ls_wR_factor_gt          0.1450
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu -0.10738(3) -0.09502(3) 0.57916(3) 0.01920(12) Uani 1 1 d . . . . .
O1 O 0.2018(2) 0.16636(19) 1.25409(17) 0.0242(5) Uani 1 1 d . . . . .
P1 P 0.24695(7) 0.26211(7) 1.16017(6) 0.01957(18) Uani 1 1 d . . . . .
C1 C 0.1529(3) 0.3388(3) 1.0581(2) 0.0215(7) Uani 1 1 d . . . . .
H1A H 0.0700 0.3519 1.0923 0.026 Uiso 1 1 calc R U . . .
H1B H 0.1730 0.4137 1.0109 0.026 Uiso 1 1 calc R U . . .
N1 N 0.1664(2) 0.2760(2) 0.9954(2) 0.0201(6) Uani 1 1 d . . . . .
C2 C 0.1219(3) 0.1709(3) 1.0576(2) 0.0212(7) Uani 1 1 d . . . . .
H2A H 0.0358 0.1898 1.0788 0.025 Uiso 1 1 calc R U . . .
H2B H 0.1574 0.1258 1.1226 0.025 Uiso 1 1 calc R U . . .
C3 C 0.1513(3) 0.1020(3) 0.9938(2) 0.0209(7) Uani 1 1 d . . . . .
H3A H 0.2373 0.0824 0.9729 0.025 Uiso 1 1 calc R U . . .
H3B H 0.1225 0.0307 1.0367 0.025 Uiso 1 1 calc R U . . .
N4 N 0.0954(2) 0.1689(2) 0.8989(2) 0.0200(6) Uani 1 1 d . . . . .
C5 C 0.1364(3) 0.2776(3) 0.8346(2) 0.0247(7) Uani 1 1 d . . . . .
H5A H 0.0962 0.3233 0.7724 0.030 Uiso 1 1 calc R U . . .
H5B H 0.2218 0.2616 0.8089 0.030 Uiso 1 1 calc R U . . .
C6 C 0.1099(3) 0.3437(3) 0.9022(2) 0.0220(7) Uani 1 1 d . . . . .
H6A H 0.1387 0.4151 0.8601 0.026 Uiso 1 1 calc R U . . .
H6B H 0.0241 0.3634 0.9244 0.026 Uiso 1 1 calc R U . . .
C11 C 0.0893(3) 0.1090(3) 0.8448(2) 0.0192(6) Uani 1 1 d . . . . .
C12 C 0.0109(3) 0.1583(3) 0.7709(2) 0.0210(7) Uani 1 1 d . . . . .
F12 F -0.05295(17) 0.26426(15) 0.75368(15) 0.0287(4) Uani 1 1 d . . . . .
C13 C -0.0059(3) 0.1031(3) 0.7203(2) 0.0194(6) Uani 1 1 d . . . . .
H13 H -0.0596 0.1403 0.6718 0.023 Uiso 1 1 calc R U . . .
C14 C 0.0555(3) -0.0089(3) 0.7394(2) 0.0182(6) Uani 1 1 d . . . . .
C15 C 0.1334(3) -0.0611(3) 0.8132(2) 0.0170(6) Uani 1 1 d . . . . .
C16 C 0.1491(3) -0.0019(3) 0.8641(2) 0.0190(6) Uani 1 1 d . . . . .
H16 H 0.2022 -0.0386 0.9131 0.023 Uiso 1 1 calc R U . . .
C17 C 0.0350(3) -0.0696(3) 0.6881(2) 0.0173(6) Uani 1 1 d . . . . .
C18 C 0.0968(3) -0.1848(3) 0.7171(2) 0.0170(6) Uani 1 1 d . . . . .
C19 C 0.1756(3) -0.2291(3) 0.7862(2) 0.0173(6) Uani 1 1 d . . . . .
H19 H 0.2202 -0.3041 0.8005 0.021 Uiso 1 1 calc R U . . .
N20 N 0.1929(2) -0.1730(2) 0.83402(19) 0.0176(5) Uani 1 1 d . . . . .
C20 C 0.2727(3) -0.2294(3) 0.9116(2) 0.0199(6) Uani 1 1 d . . . . .
H20 H 0.3448 -0.1987 0.8916 0.024 Uiso 1 1 calc R U . . .
C22 C 0.2844(3) -0.3530(3) 0.9790(3) 0.0304(8) Uani 1 1 d . . . . .
H22A H 0.3622 -0.3974 0.9985 0.037 Uiso 1 1 calc R U . . .
H22B H 0.2386 -0.3943 0.9681 0.037 Uiso 1 1 calc R U . . .
C21 C 0.2189(3) -0.2698(3) 1.0257(3) 0.0252(7) Uani 1 1 d . . . . .
H21A H 0.2561 -0.2625 1.0740 0.030 Uiso 1 1 calc R U . . .
H21B H 0.1324 -0.2593 1.0436 0.030 Uiso 1 1 calc R U . . .
C23 C 0.0834(3) -0.2633(3) 0.6769(2) 0.0196(6) Uani 1 1 d . . . . .
O24 O 0.1346(2) -0.36436(19) 0.71429(19) 0.0287(5) Uani 1 1 d . . . . .
O23 O 0.02009(19) -0.22469(18) 0.60572(17) 0.0218(5) Uani 1 1 d . . . . .
O17 O -0.03474(18) -0.01642(18) 0.62068(16) 0.0190(5) Uani 1 1 d . . . . .
C31 C 0.3842(3) 0.2128(3) 1.0915(2) 0.0203(7) Uani 1 1 d . . . . .
C32 C 0.4344(3) 0.2872(3) 0.9934(2) 0.0227(7) Uani 1 1 d . . . . .
H32 H 0.4020 0.3664 0.9677 0.027 Uiso 1 1 calc R U . . .
C33 C 0.5311(3) 0.2448(3) 0.9343(3) 0.0242(7) Uani 1 1 d . . . . .
H33 H 0.5651 0.2944 0.8675 0.029 Uiso 1 1 calc R U . . .
C34 C 0.5781(3) 0.1289(3) 0.9736(3) 0.0267(7) Uani 1 1 d . . . . .
H34 H 0.6445 0.0998 0.9330 0.032 Uiso 1 1 calc R U . . .
C35 C 0.5302(3) 0.0551(3) 1.0707(3) 0.0266(7) Uani 1 1 d . . . . .
H35 H 0.5643 -0.0238 1.0969 0.032 Uiso 1 1 calc R U . . .
C36 C 0.4319(3) 0.0971(3) 1.1295(3) 0.0240(7) Uani 1 1 d . . . . .
H36 H 0.3973 0.0469 1.1956 0.029 Uiso 1 1 calc R U . . .
C61 C 0.2637(3) 0.3666(3) 1.1952(2) 0.0206(7) Uani 1 1 d . . . . .
C62 C 0.3710(3) 0.3833(3) 1.1911(3) 0.0277(7) Uani 1 1 d . . . . .
H62 H 0.4401 0.3441 1.1615 0.033 Uiso 1 1 calc R U . . .
C63 C 0.3802(3) 0.4570(3) 1.2298(3) 0.0323(8) Uani 1 1 d . . . . .
H63 H 0.4549 0.4683 1.2260 0.039 Uiso 1 1 calc R U . . .
C64 C 0.2795(4) 0.5133(3) 1.2736(3) 0.0336(9) Uani 1 1 d . . . . .
H64 H 0.2848 0.5632 1.3005 0.040 Uiso 1 1 calc R U . . .
C65 C 0.1700(3) 0.4967(3) 1.2785(3) 0.0295(8) Uani 1 1 d . . . . .
H65 H 0.1009 0.5354 1.3086 0.035 Uiso 1 1 calc R U . . .
C66 C 0.1620(3) 0.4244(3) 1.2397(3) 0.0249(7) Uani 1 1 d . . . . .
H66 H 0.0873 0.4135 1.2431 0.030 Uiso 1 1 calc R U . . .
N41 N -0.1750(2) -0.1569(2) 0.5110(2) 0.0227(6) Uani 1 1 d . . . . .
N42 N -0.2351(2) 0.0418(2) 0.5234(2) 0.0207(6) Uani 1 1 d . . . . .
C41 C -0.1401(3) -0.2572(3) 0.5063(3) 0.0292(8) Uani 1 1 d . . . . .
H41 H -0.0740 -0.3089 0.5372 0.035 Uiso 1 1 calc R U . . .
C42 C -0.1989(4) -0.2888(3) 0.4566(3) 0.0370(9) Uani 1 1 d . . . . .
H42 H -0.1742 -0.3621 0.4563 0.044 Uiso 1 1 calc R U . . .
C43 C -0.2913(4) -0.2138(3) 0.4089(3) 0.0382(10) Uani 1 1 d . . . . .
H43 H -0.3313 -0.2349 0.3756 0.046 Uiso 1 1 calc R U . . .
C44 C -0.3274(3) -0.1050(3) 0.4091(3) 0.0305(8) Uani 1 1 d . . . . .
C45 C -0.4196(3) -0.0184(3) 0.3585(3) 0.0352(9) Uani 1 1 d . . . . .
H45 H -0.4615 -0.0333 0.3219 0.042 Uiso 1 1 calc R U . . .
C46 C -0.4490(3) 0.0850(4) 0.3615(3) 0.0358(9) Uani 1 1 d . . . . .
H46 H -0.5103 0.1412 0.3262 0.043 Uiso 1 1 calc R U . . .
C47 C -0.3886(3) 0.1113(3) 0.4173(3) 0.0278(8) Uani 1 1 d . . . . .
C48 C -0.4135(3) 0.2157(3) 0.4249(3) 0.0329(9) Uani 1 1 d . . . . .
H48 H -0.4739 0.2757 0.3916 0.039 Uiso 1 1 calc R U . . .
C49 C -0.3502(3) 0.2306(3) 0.4806(3) 0.0298(8) Uani 1 1 d . . . . .
H49 H -0.3661 0.3010 0.4857 0.036 Uiso 1 1 calc R U . . .
C50 C -0.2613(3) 0.1400(3) 0.5303(2) 0.0238(7) Uani 1 1 d . . . . .
H50 H -0.2190 0.1503 0.5699 0.029 Uiso 1 1 calc R U . . .
C51 C -0.2670(3) -0.0808(3) 0.4628(2) 0.0248(7) Uani 1 1 d . . . . .
C52 C -0.2976(3) 0.0266(3) 0.4670(2) 0.0236(7) Uani 1 1 d . . . . .
N1A N 0.4516(4) -0.2668(3) 0.3004(3) 0.0488(9) Uani 1 1 d . . . . .
O1A O 0.3439(3) -0.2337(3) 0.2931(3) 0.0651(10) Uani 1 1 d . . . . .
O2A O 0.5120(3) -0.1999(3) 0.2771(2) 0.0664(10) Uani 1 1 d . . . . .
O3A O 0.4959(3) -0.3763(3) 0.3365(2) 0.0556(8) Uani 1 1 d . . . . .
O1W O 0.3486(2) -0.4898(2) 0.7805(2) 0.0389(6) Uani 1 1 d . . . . .
O2W O 0.1219(3) -0.4796(3) 0.5961(3) 0.0644(10) Uani 1 1 d . . . . .
O3W O 0.3572(3) -0.5263(3) 0.5066(3) 0.0631(9) Uani 1 1 d . . . . .
H11W H 0.2863 -0.4525 0.7462 0.050 Uiso 1 1 d . . . . .
H21W H 0.3796 -0.5536 0.7683 0.050 Uiso 1 1 d . . . . .
H12W H 0.1082 -0.4235 0.6185 0.050 Uiso 1 1 d . . . . .
H22W H 0.1234 -0.4424 0.5243 0.050 Uiso 1 1 d . . . . .
H13W H 0.4117 -0.5302 0.4492 0.050 Uiso 1 1 d . . . . .
H23W H 0.3920 -0.5773 0.5640 0.050 Uiso 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 O23 1.917(2) . ?
Cu1 O17 1.944(2) . ?
Cu1 N41 2.008(3) . ?
Cu1 N42 2.013(3) . ?
Cu1 O1 2.243(2) 2_557 ?
Cu1 O17 2.894(2) 2_556 ?
Cu1 Cu1 3.7520(9) 2_556 ?
O1 P1 1.492(2) . ?
O1 Cu1 2.243(2) 2_557 ?
P1 C31 1.789(3) . ?
P1 C61 1.797(3) . ?
P1 C1 1.837(3) . ?
C1 N1 1.460(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
N1 C6 1.457(4) . ?
N1 C2 1.470(4) . ?
C2 C3 1.506(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N4 1.472(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
N4 C11 1.396(4) . ?
N4 C5 1.490(4) . ?
C5 C6 1.526(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C11 C16 1.388(4) . ?
C11 C12 1.423(4) . ?
C12 F12 1.351(4) . ?
C12 C13 1.356(4) . ?
C13 C14 1.406(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.415(4) . ?
C14 C17 1.449(4) . ?
C15 N20 1.396(4) . ?
C15 C16 1.399(4) . ?
C16 H16 0.9500 . ?
C17 O17 1.278(4) . ?
C17 C18 1.427(4) . ?
C18 C19 1.383(4) . ?
C18 C23 1.499(4) . ?
C19 N20 1.335(4) . ?
C19 H19 0.9500 . ?
N20 C20 1.467(4) . ?
C20 C22 1.487(4) . ?
C20 C21 1.492(4) . ?
C20 H20 1.0000 . ?
C22 C21 1.489(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C23 O24 1.241(4) . ?
C23 O23 1.278(4) . ?
C31 C36 1.389(5) . ?
C31 C32 1.405(4) . ?
C32 C33 1.381(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.389(5) . ?
C33 H33 0.9500 . ?
C34 C35 1.383(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.389(5) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C61 C62 1.375(4) . ?
C61 C66 1.405(5) . ?
C62 C63 1.401(5) . ?
C62 H62 0.9500 . ?
C63 C64 1.383(5) . ?
C63 H63 0.9500 . ?
C64 C65 1.397(5) . ?
C64 H64 0.9500 . ?
C65 C66 1.378(5) . ?
C65 H65 0.9500 . ?
C66 H66 0.9500 . ?
N41 C41 1.325(4) . ?
N41 C51 1.366(4) . ?
N42 C50 1.318(4) . ?
N42 C52 1.379(4) . ?
C41 C42 1.413(5) . ?
C41 H41 0.9500 . ?
C42 C43 1.362(6) . ?
C42 H42 0.9500 . ?
C43 C44 1.409(5) . ?
C43 H43 0.9500 . ?
C44 C51 1.405(4) . ?
C44 C45 1.424(5) . ?
C45 C46 1.357(5) . ?
C45 H45 0.9500 . ?
C46 C47 1.448(5) . ?
C46 H46 0.9500 . ?
C47 C52 1.401(5) . ?
C47 C48 1.406(5) . ?
C48 C49 1.375(5) . ?
C48 H48 0.9500 . ?
C49 C50 1.414(5) . ?
C49 H49 0.9500 . ?
C50 H50 0.9500 . ?
C51 C52 1.417(5) . ?
N1A O2A 1.215(5) . ?
N1A O1A 1.264(4) . ?
N1A O3A 1.313(5) . ?
O1W H11W 0.9063 . ?
O1W H21W 0.9096 . ?
O2W H12W 0.9126 . ?
O2W H22W 0.9192 . ?
O3W H13W 0.9150 . ?
O3W H23W 0.9138 . ?

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
O23 Cu1 O17 92.95(9) . . ?
O23 Cu1 N41 89.92(10) . . ?
O17 Cu1 N41 170.19(10) . . ?
O23 Cu1 N42 169.03(10) . . ?
O17 Cu1 N42 93.28(10) . . ?
N41 Cu1 N42 82.49(11) . . ?
O23 Cu1 O1 92.45(9) . 2_557 ?
O17 Cu1 O1 88.87(8) . 2_557 ?
N41 Cu1 O1 100.38(9) . 2_557 ?
N42 Cu1 O1 96.69(10) . 2_557 ?
O23 Cu1 O17 87.69(8) . 2_556 ?
O17 Cu1 O17 80.16(8) . 2_556 ?
N41 Cu1 O17 90.59(8) . 2_556 ?
N42 Cu1 O17 84.49(8) . 2_556 ?
O1 Cu1 O17 169.03(7) 2_557 2_556 ?
O23 Cu1 Cu1 89.75(7) . 2_556 ?
O17 Cu1 Cu1 49.46(6) . 2_556 ?
N41 Cu1 Cu1 121.24(7) . 2_556 ?
N42 Cu1 Cu1 87.46(7) . 2_556 ?
O1 Cu1 Cu1 138.33(6) 2_557 2_556 ?
O17 Cu1 Cu1 30.70(4) 2_556 2_556 ?
P1 O1 Cu1 150.67(14) . 2_557 ?
O1 P1 C31 111.48(14) . . ?
O1 P1 C61 112.19(13) . . ?
C31 P1 C61 109.03(15) . . ?
O1 P1 C1 114.00(14) . . ?
C31 P1 C1 103.42(15) . . ?
C61 P1 C1 106.19(14) . . ?
N1 C1 P1 111.8(2) . . ?
N1 C1 H1A 109.3 . . ?
P1 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
P1 C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
C6 N1 C1 112.7(2) . . ?
C6 N1 C2 109.0(2) . . ?
C1 N1 C2 112.3(2) . . ?
N1 C2 C3 110.4(3) . . ?
N1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
N4 C3 C2 108.9(3) . . ?
N4 C3 H3A 109.9 . . ?
C2 C3 H3A 109.9 . . ?
N4 C3 H3B 109.9 . . ?
C2 C3 H3B 109.9 . . ?
H3A C3 H3B 108.3 . . ?
C11 N4 C3 116.1(3) . . ?
C11 N4 C5 117.3(2) . . ?
C3 N4 C5 110.4(2) . . ?
N4 C5 C6 109.4(2) . . ?
N4 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
N4 C5 H5B 109.8 . . ?
C6 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
N1 C6 C5 110.2(3) . . ?
N1 C6 H6A 109.6 . . ?
C5 C6 H6A 109.6 . . ?
N1 C6 H6B 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C16 C11 N4 124.0(3) . . ?
C16 C11 C12 116.1(3) . . ?
N4 C11 C12 119.7(3) . . ?
F12 C12 C13 118.6(3) . . ?
F12 C12 C11 117.9(3) . . ?
C13 C12 C11 123.5(3) . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C15 117.8(3) . . ?
C13 C14 C17 120.6(3) . . ?
C15 C14 C17 121.6(3) . . ?
N20 C15 C16 121.3(3) . . ?
N20 C15 C14 118.0(3) . . ?
C16 C15 C14 120.6(3) . . ?
C11 C16 C15 121.7(3) . . ?
C11 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
O17 C17 C18 125.5(3) . . ?
O17 C17 C14 118.2(3) . . ?
C18 C17 C14 116.3(3) . . ?
C19 C18 C17 119.1(3) . . ?
C19 C18 C23 116.4(3) . . ?
C17 C18 C23 124.4(3) . . ?
N20 C19 C18 124.1(3) . . ?
N20 C19 H19 118.0 . . ?
C18 C19 H19 118.0 . . ?
C19 N20 C15 120.7(3) . . ?
C19 N20 C20 120.3(3) . . ?
C15 N20 C20 119.0(2) . . ?
N20 C20 C22 119.6(3) . . ?
N20 C20 C21 117.4(3) . . ?
C22 C20 C21 60.0(2) . . ?
N20 C20 H20 116.1 . . ?
C22 C20 H20 116.1 . . ?
C21 C20 H20 116.1 . . ?
C20 C22 C21 60.2(2) . . ?
C20 C22 H22A 117.8 . . ?
C21 C22 H22A 117.8 . . ?
C20 C22 H22B 117.8 . . ?
C21 C22 H22B 117.8 . . ?
H22A C22 H22B 114.9 . . ?
C22 C21 C20 59.9(2) . . ?
C22 C21 H21A 117.8 . . ?
C20 C21 H21A 117.8 . . ?
C22 C21 H21B 117.8 . . ?
C20 C21 H21B 117.8 . . ?
H21A C21 H21B 114.9 . . ?
O24 C23 O23 122.1(3) . . ?
O24 C23 C18 118.6(3) . . ?
O23 C23 C18 119.4(3) . . ?
C23 O23 Cu1 126.2(2) . . ?
C17 O17 Cu1 122.17(19) . . ?
C36 C31 C32 120.2(3) . . ?
C36 C31 P1 118.6(2) . . ?
C32 C31 P1 120.6(3) . . ?
C33 C32 C31 119.8(3) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C32 C33 C34 119.3(3) . . ?
C32 C33 H33 120.3 . . ?
C34 C33 H33 120.3 . . ?
C35 C34 C33 121.4(3) . . ?
C35 C34 H34 119.3 . . ?
C33 C34 H34 119.3 . . ?
C34 C35 C36 119.5(3) . . ?
C34 C35 H35 120.3 . . ?
C36 C35 H35 120.3 . . ?
C35 C36 C31 119.8(3) . . ?
C35 C36 H36 120.1 . . ?
C31 C36 H36 120.1 . . ?
C62 C61 C66 118.9(3) . . ?
C62 C61 P1 123.2(3) . . ?
C66 C61 P1 117.5(2) . . ?
C61 C62 C63 121.2(3) . . ?
C61 C62 H62 119.4 . . ?
C63 C62 H62 119.4 . . ?
C64 C63 C62 119.3(3) . . ?
C64 C63 H63 120.4 . . ?
C62 C63 H63 120.4 . . ?
C63 C64 C65 120.0(3) . . ?
C63 C64 H64 120.0 . . ?
C65 C64 H64 120.0 . . ?
C66 C65 C64 120.1(3) . . ?
C66 C65 H65 119.9 . . ?
C64 C65 H65 119.9 . . ?
C65 C66 C61 120.4(3) . . ?
C65 C66 H66 119.8 . . ?
C61 C66 H66 119.8 . . ?
C41 N41 C51 119.2(3) . . ?
C41 N41 Cu1 128.4(2) . . ?
C51 N41 Cu1 112.3(2) . . ?
C50 N42 C52 118.8(3) . . ?
C50 N42 Cu1 129.5(2) . . ?
C52 N42 Cu1 111.7(2) . . ?
N41 C41 C42 121.4(3) . . ?
N41 C41 H41 119.3 . . ?
C42 C41 H41 119.3 . . ?
C43 C42 C41 119.8(4) . . ?
C43 C42 H42 120.1 . . ?
C41 C42 H42 120.1 . . ?
C42 C43 C44 120.0(3) . . ?
C42 C43 H43 120.0 . . ?
C44 C43 H43 120.0 . . ?
C51 C44 C43 117.0(3) . . ?
C51 C44 C45 118.1(4) . . ?
C43 C44 C45 124.9(3) . . ?
C46 C45 C44 121.6(3) . . ?
C46 C45 H45 119.2 . . ?
C44 C45 H45 119.2 . . ?
C45 C46 C47 121.2(3) . . ?
C45 C46 H46 119.4 . . ?
C47 C46 H46 119.4 . . ?
C52 C47 C48 117.4(3) . . ?
C52 C47 C46 117.5(3) . . ?
C48 C47 C46 125.1(3) . . ?
C49 C48 C47 119.8(3) . . ?
C49 C48 H48 120.1 . . ?
C47 C48 H48 120.1 . . ?
C48 C49 C50 119.3(3) . . ?
C48 C49 H49 120.4 . . ?
C50 C49 H49 120.4 . . ?
N42 C50 C49 122.2(3) . . ?
N42 C50 H50 118.9 . . ?
C49 C50 H50 118.9 . . ?
N41 C51 C44 122.5(3) . . ?
N41 C51 C52 116.7(3) . . ?
C44 C51 C52 120.7(3) . . ?
N42 C52 C47 122.5(3) . . ?
N42 C52 C51 116.6(3) . . ?
C47 C52 C51 120.9(3) . . ?
O2A N1A O1A 121.2(4) . . ?
O2A N1A O3A 120.7(4) . . ?
O1A N1A O3A 118.0(4) . . ?
H11W O1W H21W 106.3 . . ?
H12W O2W H22W 105.0 . . ?
H13W O3W H23W 105.3 . . ?

_refine_diff_density_max         0.835
_refine_diff_density_min         -0.826
_refine_diff_density_rms         0.101


# start Validation Reply Form
_vrf_PLAT420_shelx               
;
PROBLEM: D-H Without Acceptor        O2W    -   H22W   ..     Please Check 
RESPONSE: Water hydrogen atoms were found using CALC-OH utility (M. Nardelli' J. Appl. Cryst., 1999, 32, 563-571) and put into the structure with fixed positions and U(iso) parameters.
;
_vrf_PLAT245_shelx               
;
PROBLEM: U(iso) H12W    Smaller than U(eq) O2W     by ...      0.015 AngSq 
RESPONSE: Water hydrogen atoms were found using CALC-OH utility (M. Nardelli' J. Appl. Cryst., 1999, 32, 563-571) and put into the structure with fixed positions and U(iso) parameters.
;
# end Validation Reply Form
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1053099'
_audit_update_record             
;
2015-03-10 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H41 Cu F I N5 O3 P, C H2 Cl2, C2 H3 N'
_chemical_formula_sum            'C47 H46 Cl2 Cu F I N6 O3 P'
_chemical_formula_weight         1054.21

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'
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'
I I -0.4742 1.8119 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.722(1)
_cell_length_b                   13.245(2)
_cell_length_c                   15.234(2)
_cell_angle_alpha                101.43(2)
_cell_angle_beta                 99.33(1)
_cell_angle_gamma                94.55(1)
_cell_volume                     2272.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8301
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      35.78

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_F_000             1068
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.365
_shelx_estimated_absorpt_T_min   0.853
_shelx_estimated_absorpt_T_max   0.910
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.8533
_exptl_absorpt_correction_T_max  0.9105
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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  'Kuma KM4CCD κ-axis diffractometer'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43533
_diffrn_reflns_av_unetI/netI     0.1767
_diffrn_reflns_av_R_equivalents  0.0755
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.883
_diffrn_reflns_theta_max         36.945
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.845
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.845
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             19449
_reflns_number_gt                9274
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1999)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         19449
_refine_ls_number_parameters     563
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1515
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   0.867
_refine_ls_restrained_S_all      0.867
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.16478(3) 0.77411(3) 0.34352(2) 0.01511(8) Uani 1 1 d . . . . .
I1 I -0.05264(2) 0.76597(2) 0.34954(2) 0.01902(6) Uani 1 1 d . . . . .
P1 P 0.29297(6) 0.71357(6) 0.43802(5) 0.01411(15) Uani 1 1 d . . . . .
C1 C 0.3435(2) 0.7910(2) 0.55567(18) 0.0158(6) Uani 1 1 d . . . . .
H1A H 0.3713 0.7456 0.5951 0.019 Uiso 1 1 calc R U . . .
H1B H 0.4081 0.8417 0.5560 0.019 Uiso 1 1 calc R U . . .
N1 N 0.2514(2) 0.84420(19) 0.59098(15) 0.0154(5) Uani 1 1 d . . . . .
C2 C 0.1547(2) 0.7702(2) 0.59652(19) 0.0172(6) Uani 1 1 d . . . . .
H2A H 0.1822 0.7251 0.6364 0.021 Uiso 1 1 calc R U . . .
H2B H 0.1238 0.7275 0.5366 0.021 Uiso 1 1 calc R U . . .
C3 C 0.0596(3) 0.8278(2) 0.63300(19) 0.0198(6) Uani 1 1 d . . . . .
H3A H 0.0300 0.8709 0.5919 0.024 Uiso 1 1 calc R U . . .
H3B H -0.0042 0.7784 0.6367 0.024 Uiso 1 1 calc R U . . .
N4 N 0.1059(2) 0.89261(19) 0.72359(16) 0.0177(5) Uani 1 1 d . . . . .
C5 C 0.2024(2) 0.9678(2) 0.7187(2) 0.0185(6) Uani 1 1 d . . . . .
H5A H 0.2336 1.0098 0.7789 0.022 Uiso 1 1 calc R U . . .
H5B H 0.1745 1.0135 0.6794 0.022 Uiso 1 1 calc R U . . .
C6 C 0.2967(2) 0.9103(2) 0.68118(19) 0.0175(6) Uani 1 1 d . . . . .
H6A H 0.3599 0.9598 0.6769 0.021 Uiso 1 1 calc R U . . .
H6B H 0.3273 0.8678 0.7225 0.021 Uiso 1 1 calc R U . . .
C11 C 0.0288(2) 0.9233(2) 0.78093(18) 0.0161(6) Uani 1 1 d . . . . .
C12 C -0.0484(3) 0.8487(2) 0.80293(19) 0.0192(6) Uani 1 1 d . . . . .
F12 F -0.04231(16) 0.74653(13) 0.76904(12) 0.0271(4) Uani 1 1 d . . . . .
C13 C -0.1251(3) 0.8729(2) 0.85952(19) 0.0176(6) Uani 1 1 d . . . . .
H13 H -0.1760 0.8209 0.8699 0.021 Uiso 1 1 calc R U . . .
C14 C -0.1271(2) 0.9770(2) 0.90242(19) 0.0166(6) Uani 1 1 d . . . . .
C15 C -0.0484(2) 1.0535(2) 0.88455(18) 0.0153(6) Uani 1 1 d . . . . .
C16 C 0.0260(2) 1.0266(2) 0.82208(18) 0.0159(6) Uani 1 1 d . . . . .
H16 H 0.0739 1.0784 0.8081 0.019 Uiso 1 1 calc R U . . .
C17 C -0.2083(2) 1.0047(2) 0.96280(18) 0.0167(6) Uani 1 1 d . . . . .
C18 C -0.1985(3) 1.1120(2) 1.00611(19) 0.0172(6) Uani 1 1 d . . . . .
C19 C -0.1206(2) 1.1822(2) 0.98581(18) 0.0163(6) Uani 1 1 d . . . . .
H19 H -0.1183 1.2516 1.0137 0.020 Uiso 1 1 calc R U . . .
N20 N -0.0471(2) 1.15710(18) 0.92797(15) 0.0146(5) Uani 1 1 d . . . . .
C23 C -0.2770(3) 1.1517(3) 1.0698(2) 0.0210(6) Uani 1 1 d . . . . .
C20 C 0.0272(2) 1.2374(2) 0.90444(19) 0.0161(6) Uani 1 1 d . . . . .
H20 H 0.0007 1.2545 0.8453 0.019 Uiso 1 1 calc R U . . .
C22 C 0.0860(3) 1.3261(2) 0.9786(2) 0.0222(7) Uani 1 1 d . . . . .
H22A H 0.0750 1.3253 1.0402 0.027 Uiso 1 1 calc R U . . .
H22B H 0.0930 1.3943 0.9645 0.027 Uiso 1 1 calc R U . . .
C21 C 0.1557(2) 1.2462(2) 0.9342(2) 0.0193(6) Uani 1 1 d . . . . .
H21A H 0.2045 1.2665 0.8936 0.023 Uiso 1 1 calc R U . . .
H21B H 0.1865 1.1975 0.9693 0.023 Uiso 1 1 calc R U . . .
O24 O -0.2710(2) 1.24152(18) 1.10840(14) 0.0265(5) Uani 1 1 d . . . . .
O23 O -0.35582(19) 1.08026(17) 1.08204(14) 0.0247(5) Uani 1 1 d . . . . .
H23 H -0.3474 1.0233 1.0526 0.037 Uiso 1 1 calc R U . . .
O17 O -0.28310(18) 0.93736(16) 0.97571(14) 0.0212(5) Uani 1 1 d . . . . .
C31 C 0.2597(2) 0.5830(2) 0.45560(18) 0.0147(6) Uani 1 1 d . . . . .
C32 C 0.1447(3) 0.5367(2) 0.42935(19) 0.0192(6) Uani 1 1 d . . . . .
H32 H 0.0879 0.5713 0.4017 0.023 Uiso 1 1 calc R U . . .
C33 C 0.1152(3) 0.4385(2) 0.4447(2) 0.0239(7) Uani 1 1 d . . . . .
H33 H 0.0384 0.4082 0.4278 0.029 Uiso 1 1 calc R U . . .
C34 C 0.1984(3) 0.3860(3) 0.4846(2) 0.0245(7) Uani 1 1 d . . . . .
H34 H 0.1778 0.3203 0.4943 0.029 Uiso 1 1 calc R U . . .
C35 C 0.3126(3) 0.4305(3) 0.5104(2) 0.0255(7) Uani 1 1 d . . . . .
H35 H 0.3690 0.3945 0.5367 0.031 Uiso 1 1 calc R U . . .
C36 C 0.3433(3) 0.5290(2) 0.4970(2) 0.0206(6) Uani 1 1 d . . . . .
H36 H 0.4200 0.5593 0.5157 0.025 Uiso 1 1 calc R U . . .
C61 C 0.4262(2) 0.7061(2) 0.39050(18) 0.0155(6) Uani 1 1 d . . . . .
C62 C 0.4363(3) 0.6177(2) 0.32597(19) 0.0191(6) Uani 1 1 d . . . . .
H62 H 0.3823 0.5594 0.3162 0.023 Uiso 1 1 calc R U . . .
C63 C 0.5264(3) 0.6155(3) 0.2760(2) 0.0218(7) Uani 1 1 d . . . . .
H63 H 0.5310 0.5565 0.2326 0.026 Uiso 1 1 calc R U . . .
C64 C 0.6084(3) 0.7004(3) 0.2909(2) 0.0222(7) Uani 1 1 d . . . . .
H64 H 0.6689 0.6984 0.2580 0.027 Uiso 1 1 calc R U . . .
C65 C 0.6007(3) 0.7888(3) 0.3549(2) 0.0222(7) Uani 1 1 d . . . . .
H65 H 0.6567 0.8457 0.3658 0.027 Uiso 1 1 calc R U . . .
C66 C 0.5086(3) 0.7924(2) 0.4033(2) 0.0196(6) Uani 1 1 d . . . . .
H66 H 0.5023 0.8529 0.4444 0.023 Uiso 1 1 calc R U . . .
N41 N 0.2158(2) 0.71479(19) 0.21704(15) 0.0165(5) Uani 1 1 d . . . . .
N42 N 0.2445(2) 0.90880(19) 0.32024(15) 0.0162(5) Uani 1 1 d . . . . .
C41 C 0.1994(3) 0.6174(2) 0.16718(19) 0.0189(6) Uani 1 1 d . . . . .
C42 C 0.2642(3) 0.5876(3) 0.0978(2) 0.0241(7) Uani 1 1 d . . . . .
H42 H 0.2509 0.5202 0.0632 0.029 Uiso 1 1 calc R U . . .
C43 C 0.3461(3) 0.6570(3) 0.0810(2) 0.0259(7) Uani 1 1 d . . . . .
H43 H 0.3891 0.6367 0.0356 0.031 Uiso 1 1 calc R U . . .
C44 C 0.3650(3) 0.7591(3) 0.13271(19) 0.0203(6) Uani 1 1 d . . . . .
C45 C 0.4458(3) 0.8384(3) 0.1182(2) 0.0256(7) Uani 1 1 d . . . . .
H45 H 0.4932 0.8214 0.0753 0.031 Uiso 1 1 calc R U . . .
C46 C 0.4547(3) 0.9365(3) 0.1648(2) 0.0238(7) Uani 1 1 d . . . . .
H46 H 0.5065 0.9867 0.1527 0.029 Uiso 1 1 calc R U . . .
C47 C 0.3850(3) 0.9655(2) 0.2335(2) 0.0202(6) Uani 1 1 d . . . . .
C48 C 0.3892(3) 1.0670(3) 0.2834(2) 0.0248(7) Uani 1 1 d . . . . .
H48 H 0.4370 1.1204 0.2718 0.030 Uiso 1 1 calc R U . . .
C49 C 0.3221(3) 1.0874(3) 0.3500(2) 0.0239(7) Uani 1 1 d . . . . .
H49 H 0.3235 1.1549 0.3826 0.029 Uiso 1 1 calc R U . . .
C50 C 0.2512(3) 1.0057(2) 0.36854(19) 0.0194(6) Uani 1 1 d . . . . .
C51 C 0.2961(2) 0.7841(2) 0.20008(18) 0.0179(6) Uani 1 1 d . . . . .
C52 C 0.3091(2) 0.8889(2) 0.25273(18) 0.0168(6) Uani 1 1 d . . . . .
C53 C 0.1103(3) 0.5427(2) 0.1876(2) 0.0250(7) Uani 1 1 d . . . . .
H53A H 0.1486 0.4946 0.2183 0.037 Uiso 1 1 calc R U . . .
H53B H 0.0619 0.5055 0.1318 0.037 Uiso 1 1 calc R U . . .
H53C H 0.0632 0.5799 0.2259 0.037 Uiso 1 1 calc R U . . .
C54 C 0.1821(3) 1.0222(2) 0.4436(2) 0.0226(7) Uani 1 1 d . . . . .
H54A H 0.1016 0.9983 0.4192 0.034 Uiso 1 1 calc R U . . .
H54B H 0.1900 1.0947 0.4713 0.034 Uiso 1 1 calc R U . . .
H54C H 0.2104 0.9842 0.4886 0.034 Uiso 1 1 calc R U . . .
C91 C 0.4612(4) 0.2783(3) 0.1444(3) 0.0474(11) Uani 1 1 d . . . . .
H911 H 0.5433 0.2709 0.1473 0.057 Uiso 1 1 calc R U . . .
H912 H 0.4181 0.2099 0.1222 0.057 Uiso 1 1 calc R U . . .
Cl91 Cl 0.41956(9) 0.35638(9) 0.06959(7) 0.0513(3) Uani 1 1 d . . . . .
Cl92 Cl 0.43550(15) 0.33132(9) 0.25644(8) 0.0741(4) Uani 1 1 d . . . . .
C93 C 0.1970(4) 0.5413(3) 0.7397(3) 0.0459(10) Uani 1 1 d . . . . .
H931 H 0.2604 0.5568 0.7099 0.069 Uiso 1 1 calc R U . . .
H932 H 0.1604 0.6028 0.7565 0.069 Uiso 1 1 calc R U . . .
H933 H 0.1412 0.4887 0.6990 0.069 Uiso 1 1 calc R U . . .
C94 C 0.2414(3) 0.5038(3) 0.8218(3) 0.0359(9) Uani 1 1 d . . . . .
N94 N 0.2745(3) 0.4747(3) 0.8822(2) 0.0432(9) 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 N42 2.068(2) . ?
Cu1 N41 2.130(2) . ?
Cu1 P1 2.2184(9) . ?
Cu1 I1 2.5596(4) . ?
P1 C31 1.823(3) . ?
P1 C61 1.827(3) . ?
P1 C1 1.856(3) . ?
C1 N1 1.453(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
N1 C2 1.463(4) . ?
N1 C6 1.466(3) . ?
C2 C3 1.517(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N4 1.467(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
N4 C11 1.385(4) . ?
N4 C5 1.468(4) . ?
C5 C6 1.515(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C11 C16 1.394(4) . ?
C11 C12 1.412(4) . ?
C12 C13 1.357(4) . ?
C12 F12 1.362(3) . ?
C13 C14 1.409(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.412(4) . ?
C14 C17 1.447(4) . ?
C15 N20 1.397(4) . ?
C15 C16 1.406(4) . ?
C16 H16 0.9300 . ?
C17 O17 1.267(4) . ?
C17 C18 1.430(4) . ?
C18 C19 1.365(4) . ?
C18 C23 1.493(4) . ?
C19 N20 1.343(3) . ?
C19 H19 0.9300 . ?
N20 C20 1.458(4) . ?
C23 O24 1.210(4) . ?
C23 O23 1.331(4) . ?
C20 C21 1.489(4) . ?
C20 C22 1.491(4) . ?
C20 H20 0.9800 . ?
C22 C21 1.509(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
O23 H23 0.8200 . ?
C31 C32 1.396(4) . ?
C31 C36 1.400(4) . ?
C32 C33 1.394(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.374(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.381(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.388(5) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C61 C66 1.397(4) . ?
C61 C62 1.399(4) . ?
C62 C63 1.397(4) . ?
C62 H62 0.9300 . ?
C63 C64 1.377(4) . ?
C63 H63 0.9300 . ?
C64 C65 1.387(4) . ?
C64 H64 0.9300 . ?
C65 C66 1.400(4) . ?
C65 H65 0.9300 . ?
C66 H66 0.9300 . ?
N41 C41 1.342(4) . ?
N41 C51 1.354(4) . ?
N42 C50 1.337(4) . ?
N42 C52 1.370(4) . ?
C41 C42 1.411(4) . ?
C41 C53 1.494(4) . ?
C42 C43 1.365(5) . ?
C42 H42 0.9300 . ?
C43 C44 1.405(5) . ?
C43 H43 0.9300 . ?
C44 C51 1.412(4) . ?
C44 C45 1.432(4) . ?
C45 C46 1.339(5) . ?
C45 H45 0.9300 . ?
C46 C47 1.442(4) . ?
C46 H46 0.9300 . ?
C47 C48 1.399(4) . ?
C47 C52 1.402(4) . ?
C48 C49 1.380(4) . ?
C48 H48 0.9300 . ?
C49 C50 1.412(4) . ?
C49 H49 0.9300 . ?
C50 C54 1.498(4) . ?
C51 C52 1.442(4) . ?
C53 H53A 0.9600 . ?
C53 H53B 0.9600 . ?
C53 H53C 0.9600 . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?
C91 Cl91 1.724(5) . ?
C91 Cl92 1.795(4) . ?
C91 H911 0.9700 . ?
C91 H912 0.9700 . ?
C93 C94 1.469(6) . ?
C93 H931 0.9600 . ?
C93 H932 0.9600 . ?
C93 H933 0.9600 . ?
C94 N94 1.093(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
N42 Cu1 N41 79.98(10) . . ?
N42 Cu1 P1 107.60(7) . . ?
N41 Cu1 P1 100.56(7) . . ?
N42 Cu1 I1 117.44(7) . . ?
N41 Cu1 I1 118.51(7) . . ?
P1 Cu1 I1 123.61(3) . . ?
C31 P1 C61 103.52(13) . . ?
C31 P1 C1 103.07(13) . . ?
C61 P1 C1 103.60(13) . . ?
C31 P1 Cu1 118.48(9) . . ?
C61 P1 Cu1 107.52(9) . . ?
C1 P1 Cu1 118.74(10) . . ?
N1 C1 P1 111.85(19) . . ?
N1 C1 H1A 109.2 . . ?
P1 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
P1 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C1 N1 C2 111.1(2) . . ?
C1 N1 C6 110.2(2) . . ?
C2 N1 C6 109.8(2) . . ?
N1 C2 C3 109.9(2) . . ?
N1 C2 H2A 109.7 . . ?
C3 C2 H2A 109.7 . . ?
N1 C2 H2B 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
N4 C3 C2 109.9(2) . . ?
N4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
N4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C11 N4 C3 118.6(2) . . ?
C11 N4 C5 119.0(2) . . ?
C3 N4 C5 110.1(2) . . ?
N4 C5 C6 109.2(2) . . ?
N4 C5 H5A 109.8 . . ?
C6 C5 H5A 109.8 . . ?
N4 C5 H5B 109.8 . . ?
C6 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
N1 C6 C5 111.1(2) . . ?
N1 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
N4 C11 C16 122.6(3) . . ?
N4 C11 C12 120.4(3) . . ?
C16 C11 C12 116.9(3) . . ?
C13 C12 F12 117.8(3) . . ?
C13 C12 C11 123.7(3) . . ?
F12 C12 C11 118.5(2) . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 118.3(3) . . ?
C13 C14 C17 120.7(3) . . ?
C15 C14 C17 121.0(3) . . ?
N20 C15 C16 120.1(3) . . ?
N20 C15 C14 119.3(2) . . ?
C16 C15 C14 120.6(3) . . ?
C11 C16 C15 120.7(3) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
O17 C17 C18 122.8(3) . . ?
O17 C17 C14 121.4(3) . . ?
C18 C17 C14 115.8(3) . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 C23 118.0(3) . . ?
C17 C18 C23 121.6(3) . . ?
N20 C19 C18 124.0(3) . . ?
N20 C19 H19 118.0 . . ?
C18 C19 H19 118.0 . . ?
C19 N20 C15 119.6(2) . . ?
C19 N20 C20 120.7(2) . . ?
C15 N20 C20 119.5(2) . . ?
O24 C23 O23 121.3(3) . . ?
O24 C23 C18 123.7(3) . . ?
O23 C23 C18 115.0(3) . . ?
N20 C20 C21 119.6(2) . . ?
N20 C20 C22 118.3(2) . . ?
C21 C20 C22 60.8(2) . . ?
N20 C20 H20 115.7 . . ?
C21 C20 H20 115.7 . . ?
C22 C20 H20 115.7 . . ?
C20 C22 C21 59.52(19) . . ?
C20 C22 H22A 117.8 . . ?
C21 C22 H22A 117.8 . . ?
C20 C22 H22B 117.8 . . ?
C21 C22 H22B 117.8 . . ?
H22A C22 H22B 115.0 . . ?
C20 C21 C22 59.66(19) . . ?
C20 C21 H21A 117.8 . . ?
C22 C21 H21A 117.8 . . ?
C20 C21 H21B 117.8 . . ?
C22 C21 H21B 117.8 . . ?
H21A C21 H21B 114.9 . . ?
C23 O23 H23 109.5 . . ?
C32 C31 C36 118.8(3) . . ?
C32 C31 P1 118.2(2) . . ?
C36 C31 P1 122.9(2) . . ?
C33 C32 C31 119.9(3) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C34 C33 C32 120.7(3) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C33 C34 C35 120.1(3) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C34 C35 C36 120.0(3) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C35 C36 C31 120.5(3) . . ?
C35 C36 H36 119.7 . . ?
C31 C36 H36 119.7 . . ?
C66 C61 C62 118.0(3) . . ?
C66 C61 P1 122.0(2) . . ?
C62 C61 P1 118.9(2) . . ?
C63 C62 C61 121.0(3) . . ?
C63 C62 H62 119.5 . . ?
C61 C62 H62 119.5 . . ?
C64 C63 C62 120.3(3) . . ?
C64 C63 H63 119.8 . . ?
C62 C63 H63 119.8 . . ?
C63 C64 C65 119.8(3) . . ?
C63 C64 H64 120.1 . . ?
C65 C64 H64 120.1 . . ?
C64 C65 C66 120.1(3) . . ?
C64 C65 H65 119.9 . . ?
C66 C65 H65 119.9 . . ?
C61 C66 C65 120.7(3) . . ?
C61 C66 H66 119.6 . . ?
C65 C66 H66 119.6 . . ?
C41 N41 C51 118.9(2) . . ?
C41 N41 Cu1 129.4(2) . . ?
C51 N41 Cu1 109.95(18) . . ?
C50 N42 C52 119.0(3) . . ?
C50 N42 Cu1 128.5(2) . . ?
C52 N42 Cu1 111.97(19) . . ?
N41 C41 C42 120.8(3) . . ?
N41 C41 C53 117.6(3) . . ?
C42 C41 C53 121.6(3) . . ?
C43 C42 C41 120.6(3) . . ?
C43 C42 H42 119.7 . . ?
C41 C42 H42 119.7 . . ?
C42 C43 C44 119.6(3) . . ?
C42 C43 H43 120.2 . . ?
C44 C43 H43 120.2 . . ?
C43 C44 C51 116.9(3) . . ?
C43 C44 C45 123.8(3) . . ?
C51 C44 C45 119.2(3) . . ?
C46 C45 C44 121.6(3) . . ?
C46 C45 H45 119.2 . . ?
C44 C45 H45 119.2 . . ?
C45 C46 C47 120.9(3) . . ?
C45 C46 H46 119.6 . . ?
C47 C46 H46 119.6 . . ?
C48 C47 C52 117.4(3) . . ?
C48 C47 C46 123.5(3) . . ?
C52 C47 C46 119.1(3) . . ?
C49 C48 C47 119.7(3) . . ?
C49 C48 H48 120.2 . . ?
C47 C48 H48 120.2 . . ?
C48 C49 C50 119.9(3) . . ?
C48 C49 H49 120.0 . . ?
C50 C49 H49 120.0 . . ?
N42 C50 C49 121.1(3) . . ?
N42 C50 C54 116.7(3) . . ?
C49 C50 C54 122.3(3) . . ?
N41 C51 C44 123.2(3) . . ?
N41 C51 C52 117.6(3) . . ?
C44 C51 C52 119.1(3) . . ?
N42 C52 C47 122.8(3) . . ?
N42 C52 C51 117.2(3) . . ?
C47 C52 C51 120.0(3) . . ?
C41 C53 H53A 109.5 . . ?
C41 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C41 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C50 C54 H54A 109.5 . . ?
C50 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C50 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
Cl91 C91 Cl92 111.4(2) . . ?
Cl91 C91 H911 109.3 . . ?
Cl92 C91 H911 109.3 . . ?
Cl91 C91 H912 109.3 . . ?
Cl92 C91 H912 109.3 . . ?
H911 C91 H912 108.0 . . ?
C94 C93 H931 109.5 . . ?
C94 C93 H932 109.5 . . ?
H931 C93 H932 109.5 . . ?
C94 C93 H933 109.5 . . ?
H931 C93 H933 109.5 . . ?
H932 C93 H933 109.5 . . ?
N94 C94 C93 179.1(4) . . ?

_refine_diff_density_max         0.903
_refine_diff_density_min         -1.243
_refine_diff_density_rms         0.129

