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

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
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data_lkm4304_0m

_audit_update_record             
;
2014-04-11 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"'chlorido[5-(triphenylphosphoniomethyl)-salicylaldehyde 4-fluorobenzoylhydrazonato] copper(II) hydrate'"
_chemical_name_common            ?
_chemical_melting_point          521-522
_chemical_formula_moiety         'C33 H26 Cl Cu F N2 O3 P'
_chemical_formula_sum            'C33 H26 Cl Cu F N2 O3 P'
_chemical_formula_weight         647.52

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   9.8737(2)
_cell_length_b                   11.0307(2)
_cell_length_c                   14.8193(3)
_cell_angle_alpha                81.3800(10)
_cell_angle_beta                 78.7180(10)
_cell_angle_gamma                72.2110(10)
_cell_volume                     1500.13(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2483
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      23.74

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8038
_exptl_absorpt_correction_T_max  0.9557
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12950
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0562
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.41
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5876
_reflns_number_gt                4273
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'pubCIF (Westrip, 2010)'

_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)+(0.0650P)²+0.6970P] 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         5876
_refine_ls_number_parameters     391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1370
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.42636(5) 0.10227(4) 0.29465(3) 0.03320(15) Uani 1 1 d . . .
P1 P 0.39315(10) 0.37252(8) 0.76923(6) 0.0312(2) Uani 1 1 d . . .
Cl1 Cl 0.26951(10) 0.04967(9) 0.22703(7) 0.0450(2) Uani 1 1 d . . .
O1 O 0.2978(2) 0.1325(3) 0.40681(17) 0.0397(6) Uani 1 1 d . . .
F1 F 1.0662(3) 0.1960(4) -0.1229(2) 0.0958(11) Uani 1 1 d . . .
O2 O 0.5647(3) 0.0916(3) 0.18227(17) 0.0422(6) Uani 1 1 d . . .
N1 N 0.5775(3) 0.1420(3) 0.3394(2) 0.0328(7) Uani 1 1 d . . .
N2 N 0.6969(3) 0.1483(3) 0.2725(2) 0.0398(7) Uani 1 1 d . . .
C23 C 0.3272(4) 0.1539(3) 0.4848(2) 0.0332(8) Uani 1 1 d . . .
C24 C 0.4632(4) 0.1634(3) 0.4973(2) 0.0307(8) Uani 1 1 d . . .
C26 C 0.5818(4) 0.1569(3) 0.4225(2) 0.0350(8) Uani 1 1 d . . .
H26 H 0.6691 0.1641 0.4359 0.042 Uiso 1 1 calc R . .
C27 C 0.6759(4) 0.1232(3) 0.1933(3) 0.0365(8) Uani 1 1 d . . .
C28 C 0.7845(4) 0.1356(4) 0.1104(3) 0.0397(9) Uani 1 1 d . . .
C33 C 0.9031(4) 0.1746(4) 0.1167(3) 0.0514(11) Uani 1 1 d . . .
H33 H 0.9184 0.1877 0.1754 0.062 Uiso 1 1 calc R . .
C32 C 0.9997(5) 0.1946(5) 0.0382(3) 0.0658(13) Uani 1 1 d . . .
H32 H 1.0809 0.2215 0.0419 0.079 Uiso 1 1 calc R . .
C31 C 0.9730(5) 0.1737(5) -0.0456(3) 0.0619(13) Uani 1 1 d . . .
C30 C 0.8607(5) 0.1323(5) -0.0542(3) 0.0590(12) Uani 1 1 d . . .
H30 H 0.8485 0.1157 -0.1128 0.071 Uiso 1 1 calc R . .
C29 C 0.7641(5) 0.1146(4) 0.0246(3) 0.0503(10) Uani 1 1 d . . .
H29 H 0.6832 0.0879 0.0199 0.060 Uiso 1 1 calc R . .
C25 C 0.4822(4) 0.1815(3) 0.5850(2) 0.0324(8) Uani 1 1 d . . .
H25 H 0.5741 0.1848 0.5932 0.039 Uiso 1 1 calc R . .
C20 C 0.3729(4) 0.1948(3) 0.6602(2) 0.0320(8) Uani 1 1 d . . .
C21 C 0.2394(4) 0.1889(4) 0.6465(3) 0.0407(9) Uani 1 1 d . . .
H21 H 0.1619 0.1988 0.6967 0.049 Uiso 1 1 calc R . .
C22 C 0.2176(4) 0.1693(4) 0.5622(3) 0.0419(9) Uani 1 1 d . . .
H22 H 0.1250 0.1659 0.5558 0.050 Uiso 1 1 calc R . .
C19 C 0.3922(4) 0.2134(3) 0.7553(2) 0.0331(8) Uani 1 1 d . . .
H19A H 0.4842 0.1526 0.7696 0.040 Uiso 1 1 calc R . .
H19B H 0.3135 0.1915 0.8010 0.040 Uiso 1 1 calc R . .
C13 C 0.5644(4) 0.3977(3) 0.7197(2) 0.0334(8) Uani 1 1 d . . .
C18 C 0.6878(4) 0.2952(4) 0.7197(3) 0.0453(10) Uani 1 1 d . . .
H18 H 0.6802 0.2114 0.7407 0.054 Uiso 1 1 calc R . .
C17 C 0.8219(5) 0.3145(4) 0.6893(3) 0.0556(11) Uani 1 1 d . . .
H17 H 0.9062 0.2440 0.6898 0.067 Uiso 1 1 calc R . .
C16 C 0.8338(5) 0.4342(4) 0.6588(3) 0.0556(11) Uani 1 1 d . . .
H16 H 0.9262 0.4468 0.6374 0.067 Uiso 1 1 calc R . .
C15 C 0.7123(5) 0.5368(4) 0.6589(3) 0.0592(12) Uani 1 1 d . . .
H15 H 0.7213 0.6201 0.6379 0.071 Uiso 1 1 calc R . .
C14 C 0.5776(5) 0.5198(4) 0.6891(3) 0.0477(10) Uani 1 1 d . . .
H14 H 0.4940 0.5910 0.6890 0.057 Uiso 1 1 calc R . .
C1 C 0.2533(4) 0.4898(3) 0.7171(3) 0.0380(9) Uani 1 1 d . . .
C2 C 0.2758(5) 0.5288(4) 0.6235(3) 0.0531(11) Uani 1 1 d . . .
H2 H 0.3646 0.4921 0.5859 0.064 Uiso 1 1 calc R . .
C3 C 0.1666(6) 0.6224(5) 0.5853(4) 0.0709(15) Uani 1 1 d . . .
H3 H 0.1816 0.6506 0.5213 0.085 Uiso 1 1 calc R . .
C4 C 0.0359(6) 0.6750(4) 0.6396(4) 0.0657(14) Uani 1 1 d . . .
H4 H -0.0374 0.7402 0.6132 0.079 Uiso 1 1 calc R . .
C5 C 0.0133(5) 0.6328(4) 0.7310(4) 0.0602(13) Uani 1 1 d . . .
H5 H -0.0773 0.6669 0.7677 0.072 Uiso 1 1 calc R . .
C6 C 0.1205(4) 0.5411(4) 0.7705(3) 0.0483(10) Uani 1 1 d . . .
H6 H 0.1038 0.5128 0.8344 0.058 Uiso 1 1 calc R . .
C7 C 0.3644(4) 0.3897(4) 0.8907(2) 0.0376(8) Uani 1 1 d . . .
C8 C 0.3396(5) 0.5096(4) 0.9196(3) 0.0566(12) Uani 1 1 d . . .
H8 H 0.3359 0.5818 0.8752 0.068 Uiso 1 1 calc R . .
C9 C 0.3205(6) 0.5246(6) 1.0116(4) 0.0776(16) Uani 1 1 d . . .
H9 H 0.3040 0.6067 1.0311 0.093 Uiso 1 1 calc R . .
C10 C 0.3253(6) 0.4203(7) 1.0753(3) 0.0789(17) Uani 1 1 d . . .
H10 H 0.3092 0.4314 1.1393 0.095 Uiso 1 1 calc R . .
C11 C 0.3527(6) 0.3008(6) 1.0487(3) 0.0736(15) Uani 1 1 d . . .
H11 H 0.3578 0.2294 1.0939 0.088 Uiso 1 1 calc R . .
C12 C 0.3731(5) 0.2836(4) 0.9555(3) 0.0567(12) Uani 1 1 d . . .
H12 H 0.3927 0.2007 0.9363 0.068 Uiso 1 1 calc R . .
O3 O 0.8700(6) 0.0724(6) 0.5518(4) 0.0519(14) Uani 0.50 1 d PG . .
H3A H 0.9300 0.0376 0.5052 0.078 Uiso 0.50 1 d PG . .
H3B H 0.9076 0.0448 0.6022 0.078 Uiso 0.50 1 d PG . .
O4 O 0.0182(9) 0.0014(9) 0.6760(10) 0.169(6) Uani 0.50 1 d P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.889(2) . ?
Cu1 O2 1.930(2) . ?
Cu1 N1 1.932(3) . ?
Cu1 Cl1 2.2516(10) . ?
P1 C1 1.789(4) . ?
P1 C13 1.793(4) . ?
P1 C7 1.797(4) . ?
P1 C19 1.801(3) . ?
O1 C23 1.315(4) . ?
F1 C31 1.364(5) . ?
O2 C27 1.294(4) . ?
N1 C26 1.277(4) . ?
N1 N2 1.397(4) . ?
N2 C27 1.313(5) . ?
C23 C22 1.406(5) . ?
C23 C24 1.427(5) . ?
C24 C25 1.401(5) . ?
C24 C26 1.438(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.483(5) . ?
C28 C29 1.388(5) . ?
C28 C33 1.389(6) . ?
C33 C32 1.388(6) . ?
C33 H33 0.9500 . ?
C32 C31 1.385(7) . ?
C32 H32 0.9500 . ?
C31 C30 1.356(7) . ?
C30 C29 1.386(6) . ?
C30 H30 0.9500 . ?
C29 H29 0.9500 . ?
C25 C20 1.382(5) . ?
C25 H25 0.9500 . ?
C20 C21 1.395(5) . ?
C20 C19 1.509(5) . ?
C21 C22 1.366(5) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C13 C18 1.386(5) . ?
C13 C14 1.391(5) . ?
C18 C17 1.383(6) . ?
C18 H18 0.9500 . ?
C17 C16 1.362(6) . ?
C17 H17 0.9500 . ?
C16 C15 1.375(6) . ?
C16 H16 0.9500 . ?
C15 C14 1.379(6) . ?
C15 H15 0.9500 . ?
C14 H14 0.9500 . ?
C1 C2 1.385(5) . ?
C1 C6 1.393(5) . ?
C2 C3 1.390(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.362(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.387(5) . ?
C7 C12 1.390(5) . ?
C8 C9 1.367(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.369(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.365(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
O3 H3A 0.8701 . ?
O3 H3B 0.8700 . ?

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 172.25(11) . . ?
O1 Cu1 N1 93.15(11) . . ?
O2 Cu1 N1 81.03(11) . . ?
O1 Cu1 Cl1 93.71(8) . . ?
O2 Cu1 Cl1 92.18(8) . . ?
N1 Cu1 Cl1 173.12(9) . . ?
C1 P1 C13 109.86(17) . . ?
C1 P1 C7 109.28(17) . . ?
C13 P1 C7 107.78(17) . . ?
C1 P1 C19 110.73(17) . . ?
C13 P1 C19 110.72(16) . . ?
C7 P1 C19 108.41(17) . . ?
C23 O1 Cu1 126.9(2) . . ?
C27 O2 Cu1 110.8(2) . . ?
C26 N1 N2 117.9(3) . . ?
C26 N1 Cu1 127.3(2) . . ?
N2 N1 Cu1 114.7(2) . . ?
C27 N2 N1 108.9(3) . . ?
O1 C23 C22 118.4(3) . . ?
O1 C23 C24 124.9(3) . . ?
C22 C23 C24 116.7(3) . . ?
C25 C24 C23 119.2(3) . . ?
C25 C24 C26 118.4(3) . . ?
C23 C24 C26 122.4(3) . . ?
N1 C26 C24 124.3(3) . . ?
N1 C26 H26 117.8 . . ?
C24 C26 H26 117.8 . . ?
O2 C27 N2 124.3(3) . . ?
O2 C27 C28 117.7(3) . . ?
N2 C27 C28 117.9(3) . . ?
C29 C28 C33 119.3(4) . . ?
C29 C28 C27 120.0(4) . . ?
C33 C28 C27 120.7(4) . . ?
C32 C33 C28 120.8(4) . . ?
C32 C33 H33 119.6 . . ?
C28 C33 H33 119.6 . . ?
C31 C32 C33 117.4(4) . . ?
C31 C32 H32 121.3 . . ?
C33 C32 H32 121.3 . . ?
C30 C31 F1 119.1(5) . . ?
C30 C31 C32 123.5(4) . . ?
F1 C31 C32 117.3(5) . . ?
C31 C30 C29 118.2(4) . . ?
C31 C30 H30 120.9 . . ?
C29 C30 H30 120.9 . . ?
C30 C29 C28 120.7(4) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C20 C25 C24 122.7(3) . . ?
C20 C25 H25 118.6 . . ?
C24 C25 H25 118.6 . . ?
C25 C20 C21 117.4(3) . . ?
C25 C20 C19 123.3(3) . . ?
C21 C20 C19 119.3(3) . . ?
C22 C21 C20 121.4(3) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C21 C22 C23 122.4(3) . . ?
C21 C22 H22 118.8 . . ?
C23 C22 H22 118.8 . . ?
C20 C19 P1 114.8(2) . . ?
C20 C19 H19A 108.6 . . ?
P1 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
P1 C19 H19B 108.6 . . ?
H19A C19 H19B 107.5 . . ?
C18 C13 C14 119.2(4) . . ?
C18 C13 P1 119.2(3) . . ?
C14 C13 P1 121.3(3) . . ?
C17 C18 C13 120.1(4) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
C16 C17 C18 120.3(4) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C16 C15 120.1(4) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C15 C14 120.5(4) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C14 C13 119.7(4) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C2 C1 C6 119.7(4) . . ?
C2 C1 P1 120.3(3) . . ?
C6 C1 P1 120.0(3) . . ?
C1 C2 C3 119.1(5) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 120.7(5) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.6(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.2(4) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C8 C7 C12 119.9(4) . . ?
C8 C7 P1 119.3(3) . . ?
C12 C7 P1 120.7(3) . . ?
C9 C8 C7 120.3(5) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.6(5) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 121.3(5) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.0(5) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 118.9(5) . . ?
C11 C12 H12 120.6 . . ?
C7 C12 H12 120.6 . . ?
H3A O3 H3B 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Cu1 O1 C23 -49.2(9) . . . . ?
N1 Cu1 O1 C23 -8.1(3) . . . . ?
Cl1 Cu1 O1 C23 171.4(3) . . . . ?
O1 Cu1 O2 C27 37.6(9) . . . . ?
N1 Cu1 O2 C27 -4.1(2) . . . . ?
Cl1 Cu1 O2 C27 177.1(2) . . . . ?
O1 Cu1 N1 C26 11.2(3) . . . . ?
O2 Cu1 N1 C26 -174.0(3) . . . . ?
Cl1 Cu1 N1 C26 -164.1(6) . . . . ?
O1 Cu1 N1 N2 -172.2(2) . . . . ?
O2 Cu1 N1 N2 2.7(2) . . . . ?
Cl1 Cu1 N1 N2 12.6(9) . . . . ?
C26 N1 N2 C27 176.2(3) . . . . ?
Cu1 N1 N2 C27 -0.8(4) . . . . ?
Cu1 O1 C23 C22 -177.5(3) . . . . ?
Cu1 O1 C23 C24 2.8(5) . . . . ?
O1 C23 C24 C25 -177.5(3) . . . . ?
C22 C23 C24 C25 2.7(5) . . . . ?
O1 C23 C24 C26 3.4(6) . . . . ?
C22 C23 C24 C26 -176.4(3) . . . . ?
N2 N1 C26 C24 174.6(3) . . . . ?
Cu1 N1 C26 C24 -8.8(5) . . . . ?
C25 C24 C26 N1 -179.3(3) . . . . ?
C23 C24 C26 N1 -0.2(6) . . . . ?
Cu1 O2 C27 N2 5.4(5) . . . . ?
Cu1 O2 C27 C28 -172.6(2) . . . . ?
N1 N2 C27 O2 -3.2(5) . . . . ?
N1 N2 C27 C28 174.9(3) . . . . ?
O2 C27 C28 C29 0.5(5) . . . . ?
N2 C27 C28 C29 -177.6(4) . . . . ?
O2 C27 C28 C33 177.2(4) . . . . ?
N2 C27 C28 C33 -1.0(5) . . . . ?
C29 C28 C33 C32 1.0(6) . . . . ?
C27 C28 C33 C32 -175.6(4) . . . . ?
C28 C33 C32 C31 -0.2(7) . . . . ?
C33 C32 C31 C30 -1.7(8) . . . . ?
C33 C32 C31 F1 178.7(4) . . . . ?
F1 C31 C30 C29 -177.7(4) . . . . ?
C32 C31 C30 C29 2.7(8) . . . . ?
C31 C30 C29 C28 -1.7(7) . . . . ?
C33 C28 C29 C30 0.0(6) . . . . ?
C27 C28 C29 C30 176.6(4) . . . . ?
C23 C24 C25 C20 -2.1(5) . . . . ?
C26 C24 C25 C20 177.0(3) . . . . ?
C24 C25 C20 C21 0.3(5) . . . . ?
C24 C25 C20 C19 179.5(3) . . . . ?
C25 C20 C21 C22 0.7(6) . . . . ?
C19 C20 C21 C22 -178.5(3) . . . . ?
C20 C21 C22 C23 0.0(6) . . . . ?
O1 C23 C22 C21 178.5(4) . . . . ?
C24 C23 C22 C21 -1.8(6) . . . . ?
C25 C20 C19 P1 77.2(4) . . . . ?
C21 C20 C19 P1 -103.6(4) . . . . ?
C1 P1 C19 C20 43.6(3) . . . . ?
C13 P1 C19 C20 -78.5(3) . . . . ?
C7 P1 C19 C20 163.5(2) . . . . ?
C1 P1 C13 C18 -153.9(3) . . . . ?
C7 P1 C13 C18 87.1(3) . . . . ?
C19 P1 C13 C18 -31.3(4) . . . . ?
C1 P1 C13 C14 32.1(4) . . . . ?
C7 P1 C13 C14 -86.9(3) . . . . ?
C19 P1 C13 C14 154.7(3) . . . . ?
C14 C13 C18 C17 -0.2(6) . . . . ?
P1 C13 C18 C17 -174.3(3) . . . . ?
C13 C18 C17 C16 -0.3(7) . . . . ?
C18 C17 C16 C15 0.6(7) . . . . ?
C17 C16 C15 C14 -0.4(7) . . . . ?
C16 C15 C14 C13 0.0(7) . . . . ?
C18 C13 C14 C15 0.3(6) . . . . ?
P1 C13 C14 C15 174.4(3) . . . . ?
C13 P1 C1 C2 38.3(4) . . . . ?
C7 P1 C1 C2 156.3(3) . . . . ?
C19 P1 C1 C2 -84.3(4) . . . . ?
C13 P1 C1 C6 -142.5(3) . . . . ?
C7 P1 C1 C6 -24.5(4) . . . . ?
C19 P1 C1 C6 94.9(3) . . . . ?
C6 C1 C2 C3 2.4(6) . . . . ?
P1 C1 C2 C3 -178.4(3) . . . . ?
C1 C2 C3 C4 -0.9(7) . . . . ?
C2 C3 C4 C5 -1.3(7) . . . . ?
C3 C4 C5 C6 2.0(7) . . . . ?
C4 C5 C6 C1 -0.5(7) . . . . ?
C2 C1 C6 C5 -1.8(6) . . . . ?
P1 C1 C6 C5 179.0(3) . . . . ?
C1 P1 C7 C8 -49.9(4) . . . . ?
C13 P1 C7 C8 69.5(4) . . . . ?
C19 P1 C7 C8 -170.7(3) . . . . ?
C1 P1 C7 C12 133.0(3) . . . . ?
C13 P1 C7 C12 -107.6(4) . . . . ?
C19 P1 C7 C12 12.3(4) . . . . ?
C12 C7 C8 C9 -1.5(7) . . . . ?
P1 C7 C8 C9 -178.6(4) . . . . ?
C7 C8 C9 C10 -0.3(8) . . . . ?
C8 C9 C10 C11 1.8(9) . . . . ?
C9 C10 C11 C12 -1.5(9) . . . . ?
C10 C11 C12 C7 -0.3(8) . . . . ?
C8 C7 C12 C11 1.8(7) . . . . ?
P1 C7 C12 C11 178.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3B O4 0.87 1.62 2.462(14) 163.2 1_655
O3 H3A O3 0.87 2.07 2.861(11) 151.3 2_756

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.075
_database_code_depnum_ccdc_archive 'CCDC 1012657'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_lkm4040_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (1,10-phenanthroline)[5-(triphenylphosphoniomethyl)-salicylaldehyde 4-fluorobenzoylhydrazonato] copper(II) monohydrate ethanol 
;
_chemical_name_common            ?
_chemical_melting_point          '423 - 424'
_chemical_formula_moiety         'C47 H39 Cl Cu F N4 O4 P'
_chemical_formula_sum            'C47 H39 Cl Cu F N4 O4 P'
_chemical_formula_weight         872.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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           Triclinic
_symmetry_space_group_name_H-M   'P-1   '
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   10.3225(8)
_cell_length_b                   14.0607(11)
_cell_length_c                   14.8610(11)
_cell_angle_alpha                107.7460(10)
_cell_angle_beta                 98.8120(10)
_cell_angle_gamma                91.6650(10)
_cell_volume                     2023.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3214
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      25.53

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             902
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6704
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19708
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_sigmaI/netI    0.0679
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         25.50
_reflns_number_total             7510
_reflns_number_gt                5461
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'pubCIF (Westrip, 2010)'

_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)+(0.0721P)²+2.8083P] 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         7510
_refine_ls_number_parameters     546
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1545
_refine_ls_wR_factor_gt          0.1347
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.011
_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 0.84723(4) 0.79428(3) 0.64728(3) 0.01834(15) Uani 1 1 d . . .
Cl1 Cl 0.17584(11) 0.58588(11) 0.16333(9) 0.0477(4) Uani 1 1 d . . .
P1 P 0.49129(10) 0.82206(8) 0.17358(8) 0.0241(3) Uani 1 1 d . . .
F1 F 1.1988(9) 1.2852(6) 1.0781(6) 0.048(2) Uani 0.50 1 d P . .
F2 F 1.2393(8) 1.2491(6) 1.0946(6) 0.0417(19) Uani 0.50 1 d P A 1
O1 O 0.6968(3) 0.71391(19) 0.5647(2) 0.0227(6) Uani 1 1 d . . .
O2 O 0.9485(3) 0.8860(2) 0.76303(19) 0.0236(6) Uani 1 1 d . . .
O3 O 0.5743(5) 0.5789(3) 0.6379(4) 0.0815(16) Uani 1 1 d . . .
H3A H 0.5900 0.6187 0.6080 0.122 Uiso 1 1 calc R . .
O4 O -0.0273(7) 0.4289(5) 0.0352(6) 0.127(2) Uani 1 1 d G . .
H4A H 0.0276 0.4787 0.0716 0.190 Uiso 1 1 d G . .
N1 N 0.7772(3) 0.9173(2) 0.6386(2) 0.0197(7) Uani 1 1 d . . .
N2 N 0.8366(3) 1.0041(2) 0.7099(3) 0.0250(8) Uani 1 1 d . . .
N3 N 0.9749(3) 0.7858(2) 0.5336(2) 0.0202(7) Uani 1 1 d . . .
N4 N 0.9503(3) 0.6773(2) 0.6554(2) 0.0189(7) Uani 1 1 d . . .
C1 C 0.6080(4) 0.7294(3) 0.1533(3) 0.0285(10) Uani 1 1 d . . .
C2 C 0.7119(4) 0.7283(4) 0.2268(3) 0.0316(10) Uani 1 1 d . . .
H2 H 0.7222 0.7778 0.2880 0.038 Uiso 1 1 calc R . .
C3 C 0.7973(4) 0.6552(4) 0.2086(4) 0.0369(12) Uani 1 1 d . . .
H3 H 0.8686 0.6554 0.2575 0.044 Uiso 1 1 calc R . .
C4 C 0.7827(5) 0.5811(4) 0.1213(4) 0.0450(14) Uani 1 1 d . . .
H4 H 0.8427 0.5304 0.1107 0.054 Uiso 1 1 calc R . .
C5 C 0.6807(5) 0.5807(4) 0.0494(4) 0.0440(13) Uani 1 1 d . . .
H5 H 0.6701 0.5294 -0.0108 0.053 Uiso 1 1 calc R . .
C6 C 0.5933(4) 0.6552(3) 0.0648(4) 0.0350(11) Uani 1 1 d . . .
H6 H 0.5237 0.6554 0.0150 0.042 Uiso 1 1 calc R . .
C7 C 0.3924(4) 0.8149(3) 0.0610(3) 0.0237(9) Uani 1 1 d . . .
C8 C 0.2797(4) 0.7492(3) 0.0257(3) 0.0277(10) Uani 1 1 d . . .
H8 H 0.2517 0.7106 0.0627 0.033 Uiso 1 1 calc R . .
C9 C 0.2083(4) 0.7406(3) -0.0642(3) 0.0320(10) Uani 1 1 d . . .
H9 H 0.1308 0.6964 -0.0885 0.038 Uiso 1 1 calc R . .
C10 C 0.2499(4) 0.7962(3) -0.1179(3) 0.0342(11) Uani 1 1 d . . .
H10 H 0.2002 0.7907 -0.1789 0.041 Uiso 1 1 calc R . .
C11 C 0.3639(5) 0.8603(3) -0.0836(3) 0.0349(11) Uani 1 1 d . . .
H11 H 0.3932 0.8975 -0.1214 0.042 Uiso 1 1 calc R . .
C12 C 0.4345(4) 0.8695(3) 0.0060(3) 0.0290(10) Uani 1 1 d . . .
H12 H 0.5123 0.9134 0.0299 0.035 Uiso 1 1 calc R . .
C13 C 0.5686(4) 0.9467(3) 0.2270(3) 0.0257(9) Uani 1 1 d . . .
C14 C 0.4857(4) 1.0225(3) 0.2549(3) 0.0270(10) Uani 1 1 d . . .
H14 H 0.3931 1.0073 0.2398 0.032 Uiso 1 1 calc R . .
C15 C 0.5365(4) 1.1202(4) 0.3047(3) 0.0314(10) Uani 1 1 d . . .
H15 H 0.4796 1.1716 0.3243 0.038 Uiso 1 1 calc R . .
C16 C 0.6720(4) 1.1413(4) 0.3254(3) 0.0353(11) Uani 1 1 d . . .
H16 H 0.7079 1.2076 0.3601 0.042 Uiso 1 1 calc R . .
C17 C 0.7553(4) 1.0669(4) 0.2960(3) 0.0356(11) Uani 1 1 d . . .
H17 H 0.8478 1.0827 0.3101 0.043 Uiso 1 1 calc R . .
C18 C 0.7046(4) 0.9692(3) 0.2460(3) 0.0281(10) Uani 1 1 d . . .
H18 H 0.7617 0.9183 0.2251 0.034 Uiso 1 1 calc R . .
C19 C 0.3876(4) 0.8021(3) 0.2550(3) 0.0275(10) Uani 1 1 d . . .
H19A H 0.3365 0.8611 0.2756 0.033 Uiso 1 1 calc R . .
H19B H 0.3246 0.7430 0.2212 0.033 Uiso 1 1 calc R . .
C20 C 0.4673(4) 0.7857(3) 0.3420(3) 0.0225(9) Uani 1 1 d . . .
C21 C 0.4705(4) 0.6872(3) 0.3464(3) 0.0247(9) Uani 1 1 d . . .
H21 H 0.4197 0.6343 0.2963 0.030 Uiso 1 1 calc R . .
C22 C 0.5450(4) 0.6662(3) 0.4209(3) 0.0242(9) Uani 1 1 d . . .
H22 H 0.5426 0.5991 0.4224 0.029 Uiso 1 1 calc R . .
C23 C 0.6256(4) 0.7410(3) 0.4959(3) 0.0216(9) Uani 1 1 d . . .
C24 C 0.6224(3) 0.8420(3) 0.4932(3) 0.0195(8) Uani 1 1 d . . .
C25 C 0.5425(4) 0.8608(3) 0.4157(3) 0.0234(9) Uani 1 1 d . . .
H25 H 0.5403 0.9277 0.4141 0.028 Uiso 1 1 calc R . .
C26 C 0.6940(4) 0.9260(3) 0.5675(3) 0.0208(9) Uani 1 1 d . . .
H26 H 0.6796 0.9914 0.5643 0.025 Uiso 1 1 calc R . .
C27 C 0.9236(4) 0.9772(3) 0.7711(3) 0.0241(9) Uani 1 1 d . . .
C28 C 1.0001(4) 1.0570(3) 0.8545(3) 0.0314(11) Uani 1 1 d . . .
C29 C 1.0845(5) 1.0268(4) 0.9216(3) 0.0430(13) Uani 1 1 d . A .
H29 H 1.0907 0.9576 0.9137 0.052 Uiso 1 1 calc R . .
C30 C 1.1596(5) 1.0987(6) 1.0001(4) 0.064(2) Uani 1 1 d . . .
H30 H 1.2174 1.0796 1.0466 0.077 Uiso 1 1 calc R A .
C31 C 1.1480(7) 1.1973(6) 1.0085(5) 0.076(3) Uani 1 1 d . A .
C32 C 1.0658(6) 1.2289(5) 0.9449(5) 0.065(2) Uani 1 1 d . . .
H32 H 1.0597 1.2985 0.9543 0.078 Uiso 1 1 calc R A .
C33 C 0.9912(5) 1.1589(3) 0.8664(4) 0.0433(13) Uani 1 1 d . A .
H33 H 0.9342 1.1798 0.8207 0.052 Uiso 1 1 calc R . .
C34 C 0.9845(4) 0.8382(3) 0.4744(3) 0.0247(9) Uani 1 1 d . . .
H34 H 0.9337 0.8942 0.4791 0.030 Uiso 1 1 calc R . .
C35 C 1.0666(4) 0.8146(3) 0.4047(3) 0.0283(10) Uani 1 1 d . . .
H35 H 1.0716 0.8543 0.3636 0.034 Uiso 1 1 calc R . .
C36 C 1.1393(4) 0.7336(3) 0.3971(3) 0.0276(10) Uani 1 1 d . . .
H36 H 1.1932 0.7153 0.3491 0.033 Uiso 1 1 calc R . .
C37 C 1.1341(4) 0.6776(3) 0.4603(3) 0.0214(9) Uani 1 1 d . . .
C38 C 1.2110(4) 0.5939(3) 0.4597(3) 0.0245(9) Uani 1 1 d . . .
H38 H 1.2673 0.5733 0.4136 0.029 Uiso 1 1 calc R . .
C39 C 1.2045(4) 0.5443(3) 0.5236(3) 0.0251(9) Uani 1 1 d . . .
H39 H 1.2588 0.4908 0.5233 0.030 Uiso 1 1 calc R . .
C40 C 1.1170(4) 0.5708(3) 0.5922(3) 0.0218(9) Uani 1 1 d . . .
C41 C 1.1055(4) 0.5199(3) 0.6586(3) 0.0260(9) Uani 1 1 d . . .
H41 H 1.1594 0.4669 0.6612 0.031 Uiso 1 1 calc R . .
C42 C 1.0168(4) 0.5465(3) 0.7198(3) 0.0266(9) Uani 1 1 d . . .
H42 H 1.0075 0.5116 0.7642 0.032 Uiso 1 1 calc R . .
C43 C 0.9400(4) 0.6258(3) 0.7159(3) 0.0235(9) Uani 1 1 d . . .
H43 H 0.8781 0.6437 0.7582 0.028 Uiso 1 1 calc R . .
C44 C 1.0373(3) 0.6503(3) 0.5934(3) 0.0174(8) Uani 1 1 d . . .
C45 C 1.0483(3) 0.7062(3) 0.5272(3) 0.0172(8) Uani 1 1 d . . .
C46 C 0.5369(11) 0.6304(5) 0.7216(5) 0.124(4) Uani 1 1 d . . .
H46 H 0.5439 0.7015 0.7404 0.148 Uiso 1 1 calc R . .
C47 C 0.4876(7) 0.5824(5) 0.7825(5) 0.074(2) Uani 1 1 d . . .
H47A H 0.4261 0.5251 0.7436 0.112 Uiso 1 1 calc R . .
H47B H 0.4418 0.6300 0.8275 0.112 Uiso 1 1 calc R . .
H47C H 0.5608 0.5590 0.8184 0.112 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.914(3) . ?
Cu1 N1 1.926(3) . ?
Cu1 O2 1.932(3) . ?
Cu1 N4 2.009(3) . ?
Cu1 N3 2.274(3) . ?
P1 C1 1.789(5) . ?
P1 C13 1.793(4) . ?
P1 C7 1.794(4) . ?
P1 C19 1.810(4) . ?
F1 F2 0.742(8) . ?
F1 C31 1.375(10) . ?
F2 C31 1.442(10) . ?
O1 C23 1.324(5) . ?
O2 C27 1.288(5) . ?
O3 C46 1.354(8) . ?
O3 H3A 0.8400 . ?
O4 H4A 0.8701 . ?
N1 C26 1.294(5) . ?
N1 N2 1.400(4) . ?
N2 C27 1.326(5) . ?
N3 C34 1.321(5) . ?
N3 C45 1.357(5) . ?
N4 C43 1.328(5) . ?
N4 C44 1.363(5) . ?
C1 C6 1.390(6) . ?
C1 C2 1.413(6) . ?
C2 C3 1.365(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.386(6) . ?
C7 C8 1.391(5) . ?
C8 C9 1.392(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.390(6) . ?
C13 C18 1.395(5) . ?
C14 C15 1.389(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(6) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.506(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C25 1.380(6) . ?
C20 C21 1.406(6) . ?
C21 C22 1.364(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.411(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.435(5) . ?
C24 C25 1.407(5) . ?
C24 C26 1.437(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.490(6) . ?
C28 C33 1.396(7) . ?
C28 C29 1.395(7) . ?
C29 C30 1.394(7) . ?
C29 H29 0.9500 . ?
C30 C31 1.364(11) . ?
C30 H30 0.9500 . ?
C31 C32 1.358(10) . ?
C32 C33 1.380(7) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 C35 1.406(6) . ?
C34 H34 0.9500 . ?
C35 C36 1.367(6) . ?
C35 H35 0.9500 . ?
C36 C37 1.404(6) . ?
C36 H36 0.9500 . ?
C37 C45 1.408(5) . ?
C37 C38 1.437(6) . ?
C38 C39 1.347(6) . ?
C38 H38 0.9500 . ?
C39 C40 1.437(6) . ?
C39 H39 0.9500 . ?
C40 C41 1.400(6) . ?
C40 C44 1.404(5) . ?
C41 C42 1.368(6) . ?
C41 H41 0.9500 . ?
C42 C43 1.396(6) . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?
C44 C45 1.450(5) . ?
C46 C47 1.425(9) . ?
C46 H46 0.9500 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N1 92.85(12) . . ?
O1 Cu1 O2 157.55(12) . . ?
N1 Cu1 O2 81.00(13) . . ?
O1 Cu1 N4 94.86(12) . . ?
N1 Cu1 N4 170.05(13) . . ?
O2 Cu1 N4 94.09(12) . . ?
O1 Cu1 N3 97.70(12) . . ?
N1 Cu1 N3 93.73(12) . . ?
O2 Cu1 N3 104.20(12) . . ?
N4 Cu1 N3 79.01(12) . . ?
C1 P1 C13 112.45(19) . . ?
C1 P1 C7 108.9(2) . . ?
C13 P1 C7 108.46(19) . . ?
C1 P1 C19 110.6(2) . . ?
C13 P1 C19 106.5(2) . . ?
C7 P1 C19 109.91(19) . . ?
F2 F1 C31 79.8(12) . . ?
F1 F2 C31 69.8(11) . . ?
C23 O1 Cu1 122.6(2) . . ?
C27 O2 Cu1 111.0(2) . . ?
C46 O3 H3A 109.5 . . ?
C26 N1 N2 118.9(3) . . ?
C26 N1 Cu1 125.4(3) . . ?
N2 N1 Cu1 115.2(2) . . ?
C27 N2 N1 108.1(3) . . ?
C34 N3 C45 118.4(3) . . ?
C34 N3 Cu1 133.1(3) . . ?
C45 N3 Cu1 108.4(2) . . ?
C43 N4 C44 118.7(3) . . ?
C43 N4 Cu1 125.1(3) . . ?
C44 N4 Cu1 116.2(3) . . ?
C6 C1 C2 119.5(4) . . ?
C6 C1 P1 119.4(3) . . ?
C2 C1 P1 121.1(4) . . ?
C3 C2 C1 119.1(5) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 121.7(4) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 119.8(5) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.1(5) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.9(4) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C12 C7 C8 120.1(4) . . ?
C12 C7 P1 119.4(3) . . ?
C8 C7 P1 120.3(3) . . ?
C7 C8 C9 119.5(4) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 120.1(4) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.5(4) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 119.5(4) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C7 120.3(4) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C14 C13 C18 119.9(4) . . ?
C14 C13 P1 116.4(3) . . ?
C18 C13 P1 123.7(4) . . ?
C15 C14 C13 120.8(4) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 118.8(4) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C17 C16 C15 120.8(4) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 120.4(4) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 119.2(4) . . ?
C17 C18 H18 120.4 . . ?
C13 C18 H18 120.4 . . ?
C20 C19 P1 111.6(3) . . ?
C20 C19 H19A 109.3 . . ?
P1 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
P1 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C25 C20 C21 117.8(4) . . ?
C25 C20 C19 123.9(4) . . ?
C21 C20 C19 118.2(4) . . ?
C22 C21 C20 121.4(4) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C21 C22 C23 122.0(4) . . ?
C21 C22 H22 119.0 . . ?
C23 C22 H22 119.0 . . ?
O1 C23 C22 118.2(3) . . ?
O1 C23 C24 124.5(3) . . ?
C22 C23 C24 117.3(4) . . ?
C25 C24 C23 118.8(4) . . ?
C25 C24 C26 118.1(3) . . ?
C23 C24 C26 123.0(3) . . ?
C20 C25 C24 122.6(4) . . ?
C20 C25 H25 118.7 . . ?
C24 C25 H25 118.7 . . ?
N1 C26 C24 123.5(3) . . ?
N1 C26 H26 118.3 . . ?
C24 C26 H26 118.3 . . ?
O2 C27 N2 124.5(4) . . ?
O2 C27 C28 117.1(4) . . ?
N2 C27 C28 118.4(4) . . ?
C33 C28 C29 119.9(4) . . ?
C33 C28 C27 122.6(5) . . ?
C29 C28 C27 117.5(4) . . ?
C30 C29 C28 119.7(6) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C31 C30 C29 118.3(6) . . ?
C31 C30 H30 120.8 . . ?
C29 C30 H30 120.9 . . ?
C32 C31 C30 123.3(5) . . ?
C32 C31 F1 103.1(8) . . ?
C30 C31 F1 133.4(8) . . ?
C32 C31 F2 133.2(8) . . ?
C30 C31 F2 103.5(8) . . ?
F1 C31 F2 30.4(4) . . ?
C31 C32 C33 119.2(6) . . ?
C31 C32 H32 120.4 . . ?
C33 C32 H32 120.4 . . ?
C32 C33 C28 119.6(6) . . ?
C32 C33 H33 120.2 . . ?
C28 C33 H33 120.2 . . ?
N3 C34 C35 122.9(4) . . ?
N3 C34 H34 118.6 . . ?
C35 C34 H34 118.6 . . ?
C36 C35 C34 118.9(4) . . ?
C36 C35 H35 120.5 . . ?
C34 C35 H35 120.5 . . ?
C35 C36 C37 119.9(4) . . ?
C35 C36 H36 120.1 . . ?
C37 C36 H36 120.1 . . ?
C36 C37 C45 117.2(4) . . ?
C36 C37 C38 123.5(4) . . ?
C45 C37 C38 119.3(4) . . ?
C39 C38 C37 121.0(4) . . ?
C39 C38 H38 119.5 . . ?
C37 C38 H38 119.5 . . ?
C38 C39 C40 121.1(4) . . ?
C38 C39 H39 119.4 . . ?
C40 C39 H39 119.4 . . ?
C41 C40 C44 117.4(4) . . ?
C41 C40 C39 122.9(4) . . ?
C44 C40 C39 119.7(4) . . ?
C42 C41 C40 120.1(4) . . ?
C42 C41 H41 120.0 . . ?
C40 C41 H41 120.0 . . ?
C41 C42 C43 119.1(4) . . ?
C41 C42 H42 120.5 . . ?
C43 C42 H42 120.5 . . ?
N4 C43 C42 122.5(4) . . ?
N4 C43 H43 118.7 . . ?
C42 C43 H43 118.7 . . ?
N4 C44 C40 122.2(4) . . ?
N4 C44 C45 118.7(3) . . ?
C40 C44 C45 119.1(4) . . ?
N3 C45 C37 122.7(4) . . ?
N3 C45 C44 117.6(3) . . ?
C37 C45 C44 119.7(3) . . ?
O3 C46 C47 122.8(6) . . ?
O3 C46 H46 118.6 . . ?
C47 C46 H46 118.6 . . ?
C46 C47 H47A 109.5 . . ?
C46 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C46 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu1 O1 C23 29.8(3) . . . . ?
O2 Cu1 O1 C23 103.0(4) . . . . ?
N4 Cu1 O1 C23 -143.8(3) . . . . ?
N3 Cu1 O1 C23 -64.3(3) . . . . ?
O1 Cu1 O2 C27 -78.9(4) . . . . ?
N1 Cu1 O2 C27 -3.5(3) . . . . ?
N4 Cu1 O2 C27 167.8(3) . . . . ?
N3 Cu1 O2 C27 88.1(3) . . . . ?
O1 Cu1 N1 C26 -26.3(3) . . . . ?
O2 Cu1 N1 C26 175.4(3) . . . . ?
N4 Cu1 N1 C26 114.4(8) . . . . ?
N3 Cu1 N1 C26 71.6(3) . . . . ?
O1 Cu1 N1 N2 162.6(3) . . . . ?
O2 Cu1 N1 N2 4.4(2) . . . . ?
N4 Cu1 N1 N2 -56.7(9) . . . . ?
N3 Cu1 N1 N2 -99.4(3) . . . . ?
C26 N1 N2 C27 -175.8(3) . . . . ?
Cu1 N1 N2 C27 -4.2(4) . . . . ?
O1 Cu1 N3 C34 85.5(4) . . . . ?
N1 Cu1 N3 C34 -7.9(4) . . . . ?
O2 Cu1 N3 C34 -89.5(4) . . . . ?
N4 Cu1 N3 C34 179.0(4) . . . . ?
O1 Cu1 N3 C45 -91.0(2) . . . . ?
N1 Cu1 N3 C45 175.6(2) . . . . ?
O2 Cu1 N3 C45 94.0(2) . . . . ?
N4 Cu1 N3 C45 2.5(2) . . . . ?
O1 Cu1 N4 C43 -84.5(3) . . . . ?
N1 Cu1 N4 C43 135.0(7) . . . . ?
O2 Cu1 N4 C43 74.9(3) . . . . ?
N3 Cu1 N4 C43 178.6(3) . . . . ?
O1 Cu1 N4 C44 95.8(3) . . . . ?
N1 Cu1 N4 C44 -44.8(9) . . . . ?
O2 Cu1 N4 C44 -104.8(3) . . . . ?
N3 Cu1 N4 C44 -1.1(2) . . . . ?
C13 P1 C1 C6 -132.6(4) . . . . ?
C7 P1 C1 C6 -12.4(4) . . . . ?
C19 P1 C1 C6 108.5(4) . . . . ?
C13 P1 C1 C2 49.7(4) . . . . ?
C7 P1 C1 C2 170.0(3) . . . . ?
C19 P1 C1 C2 -69.2(4) . . . . ?
C6 C1 C2 C3 1.2(6) . . . . ?
P1 C1 C2 C3 178.8(3) . . . . ?
C1 C2 C3 C4 -1.7(7) . . . . ?
C2 C3 C4 C5 0.9(7) . . . . ?
C3 C4 C5 C6 0.4(8) . . . . ?
C2 C1 C6 C5 0.0(7) . . . . ?
P1 C1 C6 C5 -177.7(4) . . . . ?
C4 C5 C6 C1 -0.8(7) . . . . ?
C1 P1 C7 C12 -88.0(4) . . . . ?
C13 P1 C7 C12 34.7(4) . . . . ?
C19 P1 C7 C12 150.7(4) . . . . ?
C1 P1 C7 C8 87.0(4) . . . . ?
C13 P1 C7 C8 -150.3(3) . . . . ?
C19 P1 C7 C8 -34.2(4) . . . . ?
C12 C7 C8 C9 -1.4(7) . . . . ?
P1 C7 C8 C9 -176.4(3) . . . . ?
C7 C8 C9 C10 0.6(7) . . . . ?
C8 C9 C10 C11 0.8(7) . . . . ?
C9 C10 C11 C12 -1.2(8) . . . . ?
C10 C11 C12 C7 0.3(7) . . . . ?
C8 C7 C12 C11 1.0(7) . . . . ?
P1 C7 C12 C11 176.0(4) . . . . ?
C1 P1 C13 C14 -173.2(3) . . . . ?
C7 P1 C13 C14 66.3(4) . . . . ?
C19 P1 C13 C14 -52.0(4) . . . . ?
C1 P1 C13 C18 3.0(4) . . . . ?
C7 P1 C13 C18 -117.5(4) . . . . ?
C19 P1 C13 C18 124.3(4) . . . . ?
C18 C13 C14 C15 -2.3(6) . . . . ?
P1 C13 C14 C15 174.1(3) . . . . ?
C13 C14 C15 C16 0.7(7) . . . . ?
C14 C15 C16 C17 0.8(7) . . . . ?
C15 C16 C17 C18 -0.7(7) . . . . ?
C16 C17 C18 C13 -0.9(7) . . . . ?
C14 C13 C18 C17 2.3(6) . . . . ?
P1 C13 C18 C17 -173.8(3) . . . . ?
C1 P1 C19 C20 47.6(4) . . . . ?
C13 P1 C19 C20 -74.8(3) . . . . ?
C7 P1 C19 C20 167.9(3) . . . . ?
P1 C19 C20 C25 73.9(5) . . . . ?
P1 C19 C20 C21 -103.0(4) . . . . ?
C25 C20 C21 C22 0.2(6) . . . . ?
C19 C20 C21 C22 177.2(4) . . . . ?
C20 C21 C22 C23 -1.9(6) . . . . ?
Cu1 O1 C23 C22 160.2(3) . . . . ?
Cu1 O1 C23 C24 -21.2(5) . . . . ?
C21 C22 C23 O1 -178.8(4) . . . . ?
C21 C22 C23 C24 2.6(6) . . . . ?
O1 C23 C24 C25 179.9(4) . . . . ?
C22 C23 C24 C25 -1.5(5) . . . . ?
O1 C23 C24 C26 -2.0(6) . . . . ?
C22 C23 C24 C26 176.6(4) . . . . ?
C21 C20 C25 C24 0.9(6) . . . . ?
C19 C20 C25 C24 -176.0(4) . . . . ?
C23 C24 C25 C20 -0.2(6) . . . . ?
C26 C24 C25 C20 -178.3(3) . . . . ?
N2 N1 C26 C24 -176.7(3) . . . . ?
Cu1 N1 C26 C24 12.6(5) . . . . ?
C25 C24 C26 N1 -175.1(4) . . . . ?
C23 C24 C26 N1 6.9(6) . . . . ?
Cu1 O2 C27 N2 2.3(5) . . . . ?
Cu1 O2 C27 C28 -176.8(3) . . . . ?
N1 N2 C27 O2 1.2(5) . . . . ?
N1 N2 C27 C28 -179.7(3) . . . . ?
O2 C27 C28 C33 173.9(4) . . . . ?
N2 C27 C28 C33 -5.2(6) . . . . ?
O2 C27 C28 C29 -5.2(5) . . . . ?
N2 C27 C28 C29 175.7(4) . . . . ?
C33 C28 C29 C30 -0.1(7) . . . . ?
C27 C28 C29 C30 179.1(4) . . . . ?
C28 C29 C30 C31 -0.2(7) . . . . ?
C29 C30 C31 C32 0.9(9) . . . . ?
C29 C30 C31 F1 174.8(7) . . . . ?
C29 C30 C31 F2 -178.9(5) . . . . ?
F2 F1 C31 C32 -173.1(13) . . . . ?
F2 F1 C31 C30 12.1(17) . . . . ?
F1 F2 C31 C32 9.3(17) . . . . ?
F1 F2 C31 C30 -171.0(13) . . . . ?
C30 C31 C32 C33 -1.3(9) . . . . ?
F1 C31 C32 C33 -176.8(6) . . . . ?
F2 C31 C32 C33 178.4(7) . . . . ?
C31 C32 C33 C28 0.9(8) . . . . ?
C29 C28 C33 C32 -0.3(7) . . . . ?
C27 C28 C33 C32 -179.4(4) . . . . ?
C45 N3 C34 C35 0.5(6) . . . . ?
Cu1 N3 C34 C35 -175.8(3) . . . . ?
N3 C34 C35 C36 0.5(6) . . . . ?
C34 C35 C36 C37 -2.0(6) . . . . ?
C35 C36 C37 C45 2.4(6) . . . . ?
C35 C36 C37 C38 -177.5(4) . . . . ?
C36 C37 C38 C39 178.3(4) . . . . ?
C45 C37 C38 C39 -1.6(6) . . . . ?
C37 C38 C39 C40 2.3(6) . . . . ?
C38 C39 C40 C41 178.7(4) . . . . ?
C38 C39 C40 C44 -0.5(6) . . . . ?
C44 C40 C41 C42 1.6(6) . . . . ?
C39 C40 C41 C42 -177.6(4) . . . . ?
C40 C41 C42 C43 -1.0(6) . . . . ?
C44 N4 C43 C42 1.3(6) . . . . ?
Cu1 N4 C43 C42 -178.4(3) . . . . ?
C41 C42 C43 N4 -0.5(6) . . . . ?
C43 N4 C44 C40 -0.7(5) . . . . ?
Cu1 N4 C44 C40 179.1(3) . . . . ?
C43 N4 C44 C45 179.9(3) . . . . ?
Cu1 N4 C44 C45 -0.4(4) . . . . ?
C41 C40 C44 N4 -0.8(5) . . . . ?
C39 C40 C44 N4 178.5(3) . . . . ?
C41 C40 C44 C45 178.7(3) . . . . ?
C39 C40 C44 C45 -2.1(5) . . . . ?
C34 N3 C45 C37 0.1(5) . . . . ?
Cu1 N3 C45 C37 177.2(3) . . . . ?
C34 N3 C45 C44 179.5(3) . . . . ?
Cu1 N3 C45 C44 -3.4(4) . . . . ?
C36 C37 C45 N3 -1.5(5) . . . . ?
C38 C37 C45 N3 178.4(3) . . . . ?
C36 C37 C45 C44 179.1(3) . . . . ?
C38 C37 C45 C44 -1.0(5) . . . . ?
N4 C44 C45 N3 2.8(5) . . . . ?
C40 C44 C45 N3 -176.6(3) . . . . ?
N4 C44 C45 C37 -177.8(3) . . . . ?
C40 C44 C45 C37 2.8(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O1 0.84 2.02 2.815(5) 157.9 .
O4 H4A Cl1 0.87 2.11 2.974(6) 172.9 .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.041
_refine_diff_density_min         -0.936
_refine_diff_density_rms         0.092
_database_code_depnum_ccdc_archive 'CCDC 1012658'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_lkm4416_0m

_audit_update_record             
;
2014-04-23 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 (5,5'-dimethyl-2,2'-bipyridine)[N-5-(triphenylphosphoniomethyl)-salicylaldehyde 4-fluorobenzoylhydrazonato] copper(II) dihydrate   
;
_chemical_name_common            ?
_chemical_melting_point          473
_chemical_formula_moiety         'C45 H39 Cl Cu F N4 O4 P'
_chemical_formula_sum            'C45 H39 Cl Cu F N4 O4 P'
_chemical_formula_weight         848.76

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   10.7354(4)
_cell_length_b                   13.2515(5)
_cell_length_c                   14.9015(6)
_cell_angle_alpha                80.534(3)
_cell_angle_beta                 69.109(3)
_cell_angle_gamma                81.430(3)
_cell_volume                     1944.15(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3286
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      25.11

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             878
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8925
_exptl_absorpt_correction_T_max  0.9645
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'

_exptl_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15977
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_sigmaI/netI    0.0589
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.47
_diffrn_reflns_theta_max         25.50
_reflns_number_total             7184
_reflns_number_gt                5431
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'pubCIF (Westrip, 2010)'

_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)+(0.0840P)²+0.5077P] 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         7184
_refine_ls_number_parameters     519
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1482
_refine_ls_wR_factor_gt          0.1273
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.39882(4) 0.48510(3) 0.38622(3) 0.01756(14) Uani 1 1 d . . .
Cl1 Cl 0.22281(9) 0.11401(7) 0.07709(6) 0.0241(2) Uani 1 1 d . . .
F1 F 0.9801(2) 0.01307(16) 0.38249(17) 0.0305(5) Uani 1 1 d . . .
P1 P 0.58338(9) 1.05054(6) 0.17323(6) 0.0143(2) Uani 1 1 d . . .
O1 O 0.3138(2) 0.62245(17) 0.37781(17) 0.0190(5) Uani 1 1 d . . .
O2 O 0.5135(2) 0.36623(19) 0.41868(18) 0.0229(6) Uani 1 1 d . . .
O4 O 0.056(3) 0.523(2) 0.969(3) 0.537(18) Uani 1 1 d . . .
N1 N 0.5686(3) 0.5212(2) 0.2922(2) 0.0162(6) Uani 1 1 d . . .
N2 N 0.6730(3) 0.4425(2) 0.2829(2) 0.0186(6) Uani 1 1 d . . .
N3 N 0.3086(3) 0.4226(2) 0.2946(2) 0.0209(7) Uani 1 1 d . . .
N4 N 0.2293(3) 0.4336(2) 0.4835(2) 0.0175(6) Uani 1 1 d . . .
C1 C 0.4657(3) 1.0868(2) 0.2855(2) 0.0148(7) Uani 1 1 d . . .
C2 C 0.3311(4) 1.1119(3) 0.2941(3) 0.0181(7) Uani 1 1 d . . .
H2 H 0.3039 1.1133 0.2398 0.022 Uiso 1 1 calc R . .
C3 C 0.2378(4) 1.1346(3) 0.3816(3) 0.0214(8) Uani 1 1 d . . .
H3 H 0.1458 1.1495 0.3882 0.026 Uiso 1 1 calc R . .
C4 C 0.2785(4) 1.1357(3) 0.4606(3) 0.0247(8) Uani 1 1 d . . .
H4 H 0.2140 1.1504 0.5211 0.030 Uiso 1 1 calc R . .
C5 C 0.4121(4) 1.1155(3) 0.4510(3) 0.0242(8) Uani 1 1 d . . .
H5 H 0.4397 1.1190 0.5042 0.029 Uiso 1 1 calc R . .
C6 C 0.5056(4) 1.0902(3) 0.3646(2) 0.0182(7) Uani 1 1 d . . .
H6 H 0.5973 1.0750 0.3587 0.022 Uiso 1 1 calc R . .
C7 C 0.6364(3) 1.1642(3) 0.0924(2) 0.0171(7) Uani 1 1 d . . .
C8 C 0.6470(4) 1.2506(3) 0.1304(3) 0.0233(8) Uani 1 1 d . . .
H8 H 0.6204 1.2501 0.1985 0.028 Uiso 1 1 calc R . .
C9 C 0.6958(4) 1.3368(3) 0.0698(3) 0.0313(10) Uani 1 1 d . . .
H9 H 0.7070 1.3942 0.0959 0.038 Uiso 1 1 calc R . .
C10 C 0.7287(4) 1.3397(3) -0.0295(3) 0.0305(10) Uani 1 1 d . . .
H10 H 0.7599 1.3999 -0.0711 0.037 Uiso 1 1 calc R . .
C11 C 0.7160(4) 1.2553(3) -0.0679(3) 0.0260(9) Uani 1 1 d . . .
H11 H 0.7376 1.2579 -0.1358 0.031 Uiso 1 1 calc R . .
C12 C 0.6719(4) 1.1663(3) -0.0075(3) 0.0206(8) Uani 1 1 d . . .
H12 H 0.6660 1.1075 -0.0341 0.025 Uiso 1 1 calc R . .
C13 C 0.7262(3) 0.9782(3) 0.1958(2) 0.0166(7) Uani 1 1 d . . .
C14 C 0.8555(4) 1.0003(3) 0.1404(3) 0.0226(8) Uani 1 1 d . . .
H14 H 0.8697 1.0561 0.0900 0.027 Uiso 1 1 calc R . .
C15 C 0.9645(4) 0.9413(3) 0.1581(3) 0.0286(9) Uani 1 1 d . . .
H15 H 1.0531 0.9569 0.1203 0.034 Uiso 1 1 calc R . .
C16 C 0.9429(4) 0.8600(3) 0.2309(3) 0.0308(9) Uani 1 1 d . . .
H16 H 1.0172 0.8195 0.2433 0.037 Uiso 1 1 calc R . .
C17 C 0.8134(4) 0.8367(3) 0.2864(3) 0.0239(8) Uani 1 1 d . . .
H17 H 0.7996 0.7801 0.3360 0.029 Uiso 1 1 calc R . .
C18 C 0.7054(4) 0.8957(3) 0.2695(2) 0.0193(8) Uani 1 1 d . . .
H18 H 0.6169 0.8804 0.3078 0.023 Uiso 1 1 calc R . .
C19 C 0.5094(3) 0.9738(2) 0.1196(2) 0.0150(7) Uani 1 1 d . . .
H19A H 0.4341 1.0162 0.1038 0.018 Uiso 1 1 calc R . .
H19B H 0.5771 0.9542 0.0582 0.018 Uiso 1 1 calc R . .
C20 C 0.4582(3) 0.8777(3) 0.1840(2) 0.0150(7) Uani 1 1 d . . .
C21 C 0.3258(4) 0.8788(3) 0.2501(2) 0.0180(7) Uani 1 1 d . . .
H21 H 0.2665 0.9398 0.2513 0.022 Uiso 1 1 calc R . .
C22 C 0.2813(3) 0.7928(3) 0.3128(3) 0.0177(7) Uani 1 1 d . . .
H22 H 0.1919 0.7963 0.3570 0.021 Uiso 1 1 calc R . .
C23 C 0.3643(3) 0.6993(3) 0.3137(2) 0.0160(7) Uani 1 1 d . . .
C24 C 0.4972(3) 0.6962(3) 0.2440(2) 0.0161(7) Uani 1 1 d . . .
C25 C 0.5393(3) 0.7862(3) 0.1815(2) 0.0155(7) Uani 1 1 d . . .
H25 H 0.6275 0.7838 0.1355 0.019 Uiso 1 1 calc R . .
C26 C 0.5936(3) 0.6071(3) 0.2377(2) 0.0170(7) Uani 1 1 d . . .
H26 H 0.6805 0.6119 0.1906 0.020 Uiso 1 1 calc R . .
C27 C 0.6321(3) 0.3670(3) 0.3540(2) 0.0180(8) Uani 1 1 d . . .
C28 C 0.7296(3) 0.2763(3) 0.3606(3) 0.0171(7) Uani 1 1 d . . .
C29 C 0.7104(4) 0.2145(3) 0.4491(3) 0.0218(8) Uani 1 1 d . . .
H29 H 0.6381 0.2333 0.5047 0.026 Uiso 1 1 calc R . .
C30 C 0.7946(4) 0.1267(3) 0.4571(3) 0.0233(8) Uani 1 1 d . . .
H30 H 0.7819 0.0855 0.5177 0.028 Uiso 1 1 calc R . .
C31 C 0.8970(4) 0.1003(3) 0.3755(3) 0.0221(8) Uani 1 1 d . . .
C32 C 0.9220(4) 0.1589(3) 0.2860(3) 0.0225(8) Uani 1 1 d . . .
H32 H 0.9946 0.1393 0.2309 0.027 Uiso 1 1 calc R . .
C33 C 0.8365(4) 0.2476(3) 0.2802(3) 0.0213(8) Uani 1 1 d . . .
H33 H 0.8515 0.2896 0.2200 0.026 Uiso 1 1 calc R . .
C34 C 0.3553(4) 0.4188(3) 0.1993(3) 0.0241(8) Uani 1 1 d . . .
H34 H 0.4392 0.4446 0.1632 0.029 Uiso 1 1 calc R . .
C35 C 0.2893(4) 0.3797(3) 0.1492(3) 0.0235(8) Uani 1 1 d . . .
C36 C 0.1640(4) 0.3465(3) 0.2041(3) 0.0252(9) Uani 1 1 d . . .
H36 H 0.1141 0.3197 0.1737 0.030 Uiso 1 1 calc R . .
C37 C 0.1120(4) 0.3523(3) 0.3028(3) 0.0233(8) Uani 1 1 d . . .
H37 H 0.0260 0.3308 0.3401 0.028 Uiso 1 1 calc R . .
O3 O 0.0901(8) 0.3023(5) 0.9705(5) 0.123(2) Uani 1 1 d G . .
H3A H 0.1390 0.2580 0.9946 0.185 Uiso 1 1 d G . .
H3B H 0.0084 0.2913 0.9988 0.185 Uiso 1 1 d G . .
C38 C 0.1875(3) 0.3902(2) 0.3466(3) 0.0176(7) Uani 1 1 d . . .
C39 C 0.1440(3) 0.3959(3) 0.4520(3) 0.0178(7) Uani 1 1 d . . .
C40 C 0.0210(4) 0.3672(3) 0.5177(3) 0.0194(8) Uani 1 1 d . . .
H40 H -0.0396 0.3411 0.4958 0.023 Uiso 1 1 calc R . .
C41 C -0.0122(4) 0.3768(3) 0.6144(3) 0.0209(8) Uani 1 1 d . . .
H41 H -0.0963 0.3582 0.6588 0.025 Uiso 1 1 calc R . .
C42 C 0.0763(3) 0.4136(3) 0.6477(3) 0.0181(7) Uani 1 1 d . . .
C43 C 0.1963(4) 0.4412(3) 0.5782(3) 0.0179(7) Uani 1 1 d . . .
H43 H 0.2585 0.4669 0.5988 0.022 Uiso 1 1 calc R . .
C44 C 0.0476(4) 0.4225(3) 0.7523(3) 0.0245(8) Uani 1 1 d . . .
H44A H -0.0491 0.4372 0.7844 0.037 Uiso 1 1 calc R . .
H44B H 0.0940 0.4784 0.7576 0.037 Uiso 1 1 calc R . .
H44C H 0.0790 0.3578 0.7835 0.037 Uiso 1 1 calc R . .
C45 C 0.3490(4) 0.3734(3) 0.0421(3) 0.0325(10) Uani 1 1 d . . .
H45A H 0.4287 0.4111 0.0147 0.049 Uiso 1 1 calc R . .
H45B H 0.2831 0.4037 0.0113 0.049 Uiso 1 1 calc R . .
H45C H 0.3742 0.3012 0.0307 0.049 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.917(2) . ?
Cu1 N1 1.932(3) . ?
Cu1 O2 1.956(2) . ?
Cu1 N4 2.011(3) . ?
Cu1 N3 2.246(3) . ?
F1 C31 1.365(4) . ?
P1 C1 1.789(3) . ?
P1 C13 1.790(4) . ?
P1 C7 1.793(3) . ?
P1 C19 1.807(3) . ?
O1 C23 1.312(4) . ?
O2 C27 1.295(4) . ?
O4 O4 1.38(5) 2_567 ?
N1 C26 1.287(4) . ?
N1 N2 1.397(4) . ?
N2 C27 1.329(4) . ?
N3 C34 1.333(5) . ?
N3 C38 1.347(5) . ?
N4 C43 1.345(4) . ?
N4 C39 1.352(4) . ?
C1 C2 1.398(5) . ?
C1 C6 1.399(5) . ?
C2 C3 1.380(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.396(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.393(5) . ?
C7 C12 1.396(5) . ?
C8 C9 1.377(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.384(5) . ?
C13 C18 1.399(5) . ?
C14 C15 1.389(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.375(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.509(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C25 1.380(5) . ?
C20 C21 1.411(5) . ?
C21 C22 1.376(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.415(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.433(5) . ?
C24 C25 1.411(5) . ?
C24 C26 1.441(5) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.487(5) . ?
C28 C33 1.391(5) . ?
C28 C29 1.399(5) . ?
C29 C30 1.379(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.372(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.385(5) . ?
C32 C33 1.390(5) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 C35 1.394(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.394(5) . ?
C35 C45 1.504(5) . ?
C36 C37 1.385(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.393(5) . ?
C37 H37 0.9500 . ?
O3 H3A 0.8500 . ?
O3 H3B 0.8499 . ?
C38 C39 1.482(5) . ?
C39 C40 1.397(5) . ?
C40 C41 1.378(5) . ?
C40 H40 0.9500 . ?
C41 C42 1.393(5) . ?
C41 H41 0.9500 . ?
C42 C43 1.389(5) . ?
C42 C44 1.499(5) . ?
C43 H43 0.9500 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N1 93.75(11) . . ?
O1 Cu1 O2 160.69(10) . . ?
N1 Cu1 O2 81.29(11) . . ?
O1 Cu1 N4 91.55(11) . . ?
N1 Cu1 N4 174.64(12) . . ?
O2 Cu1 N4 93.96(11) . . ?
O1 Cu1 N3 96.73(11) . . ?
N1 Cu1 N3 101.48(11) . . ?
O2 Cu1 N3 102.53(11) . . ?
N4 Cu1 N3 77.02(11) . . ?
C1 P1 C13 108.57(16) . . ?
C1 P1 C7 109.13(16) . . ?
C13 P1 C7 108.69(16) . . ?
C1 P1 C19 110.74(16) . . ?
C13 P1 C19 109.77(16) . . ?
C7 P1 C19 109.91(15) . . ?
C23 O1 Cu1 125.7(2) . . ?
C27 O2 Cu1 109.3(2) . . ?
C26 N1 N2 118.2(3) . . ?
C26 N1 Cu1 127.4(2) . . ?
N2 N1 Cu1 114.4(2) . . ?
C27 N2 N1 108.6(3) . . ?
C34 N3 C38 118.7(3) . . ?
C34 N3 Cu1 129.2(2) . . ?
C38 N3 Cu1 112.0(2) . . ?
C43 N4 C39 119.7(3) . . ?
C43 N4 Cu1 121.1(2) . . ?
C39 N4 Cu1 119.1(2) . . ?
C2 C1 C6 119.5(3) . . ?
C2 C1 P1 119.1(3) . . ?
C6 C1 P1 121.4(3) . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.0(4) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C8 C7 C12 119.7(3) . . ?
C8 C7 P1 118.9(3) . . ?
C12 C7 P1 121.3(3) . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.9(4) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 119.4(3) . . ?
C11 C12 H12 120.3 . . ?
C7 C12 H12 120.3 . . ?
C14 C13 C18 119.8(3) . . ?
C14 C13 P1 121.6(3) . . ?
C18 C13 P1 118.5(3) . . ?
C13 C14 C15 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 119.4(4) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.7(4) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 120.0(4) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C13 119.8(4) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
C20 C19 P1 113.6(2) . . ?
C20 C19 H19A 108.9 . . ?
P1 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
P1 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C25 C20 C21 117.7(3) . . ?
C25 C20 C19 121.4(3) . . ?
C21 C20 C19 120.9(3) . . ?
C22 C21 C20 121.0(3) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C23 122.1(3) . . ?
C21 C22 H22 118.9 . . ?
C23 C22 H22 118.9 . . ?
O1 C23 C22 117.6(3) . . ?
O1 C23 C24 125.2(3) . . ?
C22 C23 C24 117.3(3) . . ?
C25 C24 C23 118.8(3) . . ?
C25 C24 C26 117.7(3) . . ?
C23 C24 C26 123.4(3) . . ?
C20 C25 C24 123.0(3) . . ?
C20 C25 H25 118.5 . . ?
C24 C25 H25 118.5 . . ?
N1 C26 C24 123.7(3) . . ?
N1 C26 H26 118.2 . . ?
C24 C26 H26 118.2 . . ?
O2 C27 N2 125.1(3) . . ?
O2 C27 C28 117.0(3) . . ?
N2 C27 C28 117.9(3) . . ?
C33 C28 C29 118.5(3) . . ?
C33 C28 C27 122.2(3) . . ?
C29 C28 C27 119.3(3) . . ?
C30 C29 C28 121.1(3) . . ?
C30 C29 H29 119.4 . . ?
C28 C29 H29 119.4 . . ?
C31 C30 C29 118.3(3) . . ?
C31 C30 H30 120.8 . . ?
C29 C30 H30 120.8 . . ?
F1 C31 C30 118.7(3) . . ?
F1 C31 C32 118.0(3) . . ?
C30 C31 C32 123.3(3) . . ?
C31 C32 C33 117.2(3) . . ?
C31 C32 H32 121.4 . . ?
C33 C32 H32 121.4 . . ?
C32 C33 C28 121.6(3) . . ?
C32 C33 H33 119.2 . . ?
C28 C33 H33 119.2 . . ?
N3 C34 C35 124.4(3) . . ?
N3 C34 H34 117.8 . . ?
C35 C34 H34 117.8 . . ?
C36 C35 C34 116.1(3) . . ?
C36 C35 C45 121.6(3) . . ?
C34 C35 C45 122.3(4) . . ?
C37 C36 C35 120.4(3) . . ?
C37 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
C36 C37 C38 119.1(3) . . ?
C36 C37 H37 120.5 . . ?
C38 C37 H37 120.5 . . ?
H3A O3 H3B 109.5 . . ?
N3 C38 C37 121.2(3) . . ?
N3 C38 C39 115.2(3) . . ?
C37 C38 C39 123.6(3) . . ?
N4 C39 C40 119.9(3) . . ?
N4 C39 C38 116.4(3) . . ?
C40 C39 C38 123.7(3) . . ?
C41 C40 C39 119.7(3) . . ?
C41 C40 H40 120.2 . . ?
C39 C40 H40 120.2 . . ?
C40 C41 C42 120.8(3) . . ?
C40 C41 H41 119.6 . . ?
C42 C41 H41 119.6 . . ?
C43 C42 C41 116.3(3) . . ?
C43 C42 C44 120.6(3) . . ?
C41 C42 C44 123.1(3) . . ?
N4 C43 C42 123.6(3) . . ?
N4 C43 H43 118.2 . . ?
C42 C43 H43 118.2 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C35 C45 H45A 109.5 . . ?
C35 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C35 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu1 O1 C23 9.4(3) . . . . ?
O2 Cu1 O1 C23 83.7(4) . . . . ?
N4 Cu1 O1 C23 -169.7(3) . . . . ?
N3 Cu1 O1 C23 -92.6(3) . . . . ?
O1 Cu1 O2 C27 -85.4(4) . . . . ?
N1 Cu1 O2 C27 -9.1(2) . . . . ?
N4 Cu1 O2 C27 168.3(2) . . . . ?
N3 Cu1 O2 C27 90.8(2) . . . . ?
O1 Cu1 N1 C26 -9.3(3) . . . . ?
O2 Cu1 N1 C26 -170.5(3) . . . . ?
N4 Cu1 N1 C26 161.6(11) . . . . ?
N3 Cu1 N1 C26 88.3(3) . . . . ?
O1 Cu1 N1 N2 172.1(2) . . . . ?
O2 Cu1 N1 N2 10.9(2) . . . . ?
N4 Cu1 N1 N2 -17.0(13) . . . . ?
N3 Cu1 N1 N2 -90.2(2) . . . . ?
C26 N1 N2 C27 171.2(3) . . . . ?
Cu1 N1 N2 C27 -10.1(3) . . . . ?
O1 Cu1 N3 C34 90.7(3) . . . . ?
N1 Cu1 N3 C34 -4.5(3) . . . . ?
O2 Cu1 N3 C34 -88.0(3) . . . . ?
N4 Cu1 N3 C34 -179.3(3) . . . . ?
O1 Cu1 N3 C38 -85.8(2) . . . . ?
N1 Cu1 N3 C38 179.0(2) . . . . ?
O2 Cu1 N3 C38 95.5(2) . . . . ?
N4 Cu1 N3 C38 4.2(2) . . . . ?
O1 Cu1 N4 C43 -84.0(3) . . . . ?
N1 Cu1 N4 C43 105.1(12) . . . . ?
O2 Cu1 N4 C43 77.5(3) . . . . ?
N3 Cu1 N4 C43 179.5(3) . . . . ?
O1 Cu1 N4 C39 92.5(3) . . . . ?
N1 Cu1 N4 C39 -78.4(13) . . . . ?
O2 Cu1 N4 C39 -106.0(3) . . . . ?
N3 Cu1 N4 C39 -4.0(2) . . . . ?
C13 P1 C1 C2 -158.3(3) . . . . ?
C7 P1 C1 C2 83.4(3) . . . . ?
C19 P1 C1 C2 -37.7(3) . . . . ?
C13 P1 C1 C6 21.4(3) . . . . ?
C7 P1 C1 C6 -96.9(3) . . . . ?
C19 P1 C1 C6 142.0(3) . . . . ?
C6 C1 C2 C3 -3.3(5) . . . . ?
P1 C1 C2 C3 176.5(3) . . . . ?
C1 C2 C3 C4 2.0(5) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C3 C4 C5 C6 -2.5(5) . . . . ?
C4 C5 C6 C1 1.2(5) . . . . ?
C2 C1 C6 C5 1.7(5) . . . . ?
P1 C1 C6 C5 -178.1(3) . . . . ?
C1 P1 C7 C8 33.7(3) . . . . ?
C13 P1 C7 C8 -84.5(3) . . . . ?
C19 P1 C7 C8 155.3(3) . . . . ?
C1 P1 C7 C12 -148.7(3) . . . . ?
C13 P1 C7 C12 93.0(3) . . . . ?
C19 P1 C7 C12 -27.1(3) . . . . ?
C12 C7 C8 C9 -1.9(6) . . . . ?
P1 C7 C8 C9 175.7(3) . . . . ?
C7 C8 C9 C10 3.1(6) . . . . ?
C8 C9 C10 C11 -1.8(7) . . . . ?
C9 C10 C11 C12 -0.8(6) . . . . ?
C10 C11 C12 C7 2.0(6) . . . . ?
C8 C7 C12 C11 -0.7(5) . . . . ?
P1 C7 C12 C11 -178.3(3) . . . . ?
C1 P1 C13 C14 -131.3(3) . . . . ?
C7 P1 C13 C14 -12.7(3) . . . . ?
C19 P1 C13 C14 107.5(3) . . . . ?
C1 P1 C13 C18 50.6(3) . . . . ?
C7 P1 C13 C18 169.2(3) . . . . ?
C19 P1 C13 C18 -70.6(3) . . . . ?
C18 C13 C14 C15 -0.4(5) . . . . ?
P1 C13 C14 C15 -178.5(3) . . . . ?
C13 C14 C15 C16 0.5(6) . . . . ?
C14 C15 C16 C17 0.1(6) . . . . ?
C15 C16 C17 C18 -0.7(6) . . . . ?
C16 C17 C18 C13 0.7(5) . . . . ?
C14 C13 C18 C17 -0.2(5) . . . . ?
P1 C13 C18 C17 177.9(3) . . . . ?
C1 P1 C19 C20 -57.8(3) . . . . ?
C13 P1 C19 C20 62.1(3) . . . . ?
C7 P1 C19 C20 -178.4(2) . . . . ?
P1 C19 C20 C25 -89.7(3) . . . . ?
P1 C19 C20 C21 89.4(3) . . . . ?
C25 C20 C21 C22 2.9(5) . . . . ?
C19 C20 C21 C22 -176.2(3) . . . . ?
C20 C21 C22 C23 -0.8(5) . . . . ?
Cu1 O1 C23 C22 173.9(2) . . . . ?
Cu1 O1 C23 C24 -6.0(5) . . . . ?
C21 C22 C23 O1 178.3(3) . . . . ?
C21 C22 C23 C24 -1.8(5) . . . . ?
O1 C23 C24 C25 -177.9(3) . . . . ?
C22 C23 C24 C25 2.2(5) . . . . ?
O1 C23 C24 C26 -1.4(5) . . . . ?
C22 C23 C24 C26 178.7(3) . . . . ?
C21 C20 C25 C24 -2.5(5) . . . . ?
C19 C20 C25 C24 176.6(3) . . . . ?
C23 C24 C25 C20 -0.1(5) . . . . ?
C26 C24 C25 C20 -176.8(3) . . . . ?
N2 N1 C26 C24 -176.2(3) . . . . ?
Cu1 N1 C26 C24 5.4(5) . . . . ?
C25 C24 C26 N1 178.3(3) . . . . ?
C23 C24 C26 N1 1.8(5) . . . . ?
Cu1 O2 C27 N2 6.6(4) . . . . ?
Cu1 O2 C27 C28 -173.5(2) . . . . ?
N1 N2 C27 O2 2.1(5) . . . . ?
N1 N2 C27 C28 -177.7(3) . . . . ?
O2 C27 C28 C33 154.5(3) . . . . ?
N2 C27 C28 C33 -25.7(5) . . . . ?
O2 C27 C28 C29 -22.4(4) . . . . ?
N2 C27 C28 C29 157.4(3) . . . . ?
C33 C28 C29 C30 -0.4(5) . . . . ?
C27 C28 C29 C30 176.6(3) . . . . ?
C28 C29 C30 C31 -1.0(5) . . . . ?
C29 C30 C31 F1 -179.4(3) . . . . ?
C29 C30 C31 C32 1.7(5) . . . . ?
F1 C31 C32 C33 -179.9(3) . . . . ?
C30 C31 C32 C33 -1.0(5) . . . . ?
C31 C32 C33 C28 -0.4(5) . . . . ?
C29 C28 C33 C32 1.1(5) . . . . ?
C27 C28 C33 C32 -175.9(3) . . . . ?
C38 N3 C34 C35 -2.5(6) . . . . ?
Cu1 N3 C34 C35 -178.8(3) . . . . ?
N3 C34 C35 C36 2.5(6) . . . . ?
N3 C34 C35 C45 -177.5(4) . . . . ?
C34 C35 C36 C37 -0.6(5) . . . . ?
C45 C35 C36 C37 179.4(4) . . . . ?
C35 C36 C37 C38 -1.1(6) . . . . ?
C34 N3 C38 C37 0.6(5) . . . . ?
Cu1 N3 C38 C37 177.5(3) . . . . ?
C34 N3 C38 C39 179.3(3) . . . . ?
Cu1 N3 C38 C39 -3.8(4) . . . . ?
C36 C37 C38 N3 1.1(5) . . . . ?
C36 C37 C38 C39 -177.4(3) . . . . ?
C43 N4 C39 C40 1.5(5) . . . . ?
Cu1 N4 C39 C40 -175.1(2) . . . . ?
C43 N4 C39 C38 179.9(3) . . . . ?
Cu1 N4 C39 C38 3.3(4) . . . . ?
N3 C38 C39 N4 0.7(5) . . . . ?
C37 C38 C39 N4 179.4(3) . . . . ?
N3 C38 C39 C40 179.1(3) . . . . ?
C37 C38 C39 C40 -2.3(5) . . . . ?
N4 C39 C40 C41 -0.5(5) . . . . ?
C38 C39 C40 C41 -178.8(3) . . . . ?
C39 C40 C41 C42 -0.9(5) . . . . ?
C40 C41 C42 C43 1.2(5) . . . . ?
C40 C41 C42 C44 -178.0(3) . . . . ?
C39 N4 C43 C42 -1.1(5) . . . . ?
Cu1 N4 C43 C42 175.4(3) . . . . ?
C41 C42 C43 N4 -0.3(5) . . . . ?
C44 C42 C43 N4 178.9(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A Cl1 0.85 2.34 3.167(5) 165.0 1_556

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.099
_database_code_depnum_ccdc_archive 'CCDC 1012659'
