# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1036445'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'complex of tris(2-pyridyl)phosphine with nickel hexafluoroacetylacetonate'
_chemical_name_common            ?
_chemical_melting_point          425
_chemical_formula_moiety         'C20 H15 F6 N3 Ni O4 P, C5 H F6 O2'
_chemical_formula_sum            'C25 H16 F12 N3 Ni O6 P'
_chemical_formula_weight         772.07

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   8.8330(8)
_cell_length_b                   15.6509(15)
_cell_length_c                   21.6876(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2998.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_F_000             1544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.820
_shelx_estimated_absorpt_T_min   0.685
_shelx_estimated_absorpt_T_max   0.901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.686
_exptl_absorpt_correction_T_max  0.902
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            94343
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.285
_diffrn_reflns_theta_max         30.112
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8828
_reflns_number_gt                7699
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0298P)²+1.4075P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3085 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.014(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8828
_refine_ls_number_parameters     457
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0746
_refine_ls_wR_factor_gt          0.0707
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
Ni1 Ni 0.85478(4) 0.86531(2) 0.79545(2) 0.01128(8) Uani 1 1 d . . . A 1
P1 P 0.89879(8) 0.68473(4) 0.72432(3) 0.01180(13) Uani 1 1 d . . . B 1
O1 O 0.9172(3) 0.97951(13) 0.75935(9) 0.0190(4) Uani 1 1 d . . . A 1
H15 H 0.9418 0.9731 0.7232 0.029 Uiso 1 1 calc R U . A 1
O3 O 0.6553(2) 0.92306(12) 0.82009(8) 0.0155(4) Uani 1 1 d . . . A 1
F3 F 0.3902(2) 0.99203(15) 0.87375(12) 0.0454(6) Uani 1 1 d . . . C 1
F4 F 0.5066(2) 1.11247(13) 0.87811(11) 0.0438(6) Uani 1 1 d . . . D 1
F5 F 0.4680(3) 1.05284(15) 0.79148(10) 0.0446(6) Uani 1 1 d . . . E 1
F6 F 0.9902(3) 1.09118(13) 0.96291(9) 0.0363(5) Uani 1 1 d . . . F 1
F7 F 0.9644(3) 0.97219(13) 1.00931(8) 0.0345(5) Uani 1 1 d . . . G 1
F8 F 1.1430(2) 0.98884(17) 0.94448(10) 0.0502(7) Uani 1 1 d . . . H 1
F9 F -0.0976(3) 0.28345(14) 0.92386(11) 0.0486(6) Uani 1 1 d . . . I 1
F10 F -0.1250(4) 0.36782(19) 0.99996(10) 0.0762(10) Uani 1 1 d . . . J 1
F11 F -0.2884(3) 0.3654(2) 0.92944(15) 0.0702(9) Uani 1 1 d . . . K 1
F12 F 0.039(4) 0.6427(11) 1.0048(4) 0.082(6) Uani 0.44(4) 1 d . . P L 1
N3 N 0.7773(3) 0.74944(15) 0.82877(10) 0.0135(4) Uani 1 1 d . . . . .
O2 O 0.9412(2) 0.90676(12) 0.87843(8) 0.0155(4) Uani 1 1 d . . . . .
F1 F 0.0533(4) 0.71590(16) 0.92768(14) 0.0679(9) Uani 1 1 d . . . . .
O4 O -0.0549(3) 0.41597(15) 0.84597(9) 0.0264(5) Uani 1 1 d . . . . .
O5 O 0.0937(3) 0.57960(17) 0.84820(11) 0.0349(6) Uani 1 1 d . . . . .
N1 N 1.0628(3) 0.81151(15) 0.77497(10) 0.0139(4) Uani 1 1 d . . . . .
N2 N 0.7638(2) 0.83727(14) 0.70923(10) 0.0131(4) Uani 1 1 d . . . . .
O6 O 0.9151(2) 0.60307(12) 0.69067(8) 0.0176(4) Uani 1 1 d . . . . .
C1 C 1.1906(3) 0.85184(19) 0.78982(13) 0.0195(6) Uani 1 1 d . . . . .
H1 H 1.1844 0.9032 0.8112 0.023 Uiso 1 1 calc R U . . .
C2 C 1.3325(3) 0.8203(2) 0.77461(15) 0.0271(7) Uani 1 1 d . . . . .
H2 H 1.4196 0.8496 0.7861 0.033 Uiso 1 1 calc R U . . .
C3 C 1.3422(4) 0.7448(2) 0.74230(16) 0.0297(7) Uani 1 1 d . . . . .
H3 H 1.4362 0.7229 0.7312 0.036 Uiso 1 1 calc R U . . .
C4 C 1.2114(3) 0.7019(2) 0.72659(15) 0.0225(6) Uani 1 1 d . . . . .
H12 H 1.2153 0.6505 0.7051 0.027 Uiso 1 1 calc R U . . .
C5 C 1.0747(3) 0.73739(18) 0.74369(12) 0.0144(5) Uani 1 1 d . . . . .
C6 C 0.7933(3) 0.76276(17) 0.68055(12) 0.0119(5) Uani 1 1 d . . . . .
C7 C 0.6862(3) 0.89668(18) 0.67836(13) 0.0182(6) Uani 1 1 d . . . . .
H7 H 0.6646 0.9483 0.6977 0.022 Uiso 1 1 calc R U . . .
C8 C 0.6367(4) 0.88370(18) 0.61828(13) 0.0226(6) Uani 1 1 d . . . . .
H6 H 0.5836 0.9264 0.5977 0.027 Uiso 1 1 calc R U . . .
C9 C 0.6670(4) 0.8071(2) 0.58931(13) 0.0219(6) Uani 1 1 d . . . . .
H5 H 0.6339 0.7973 0.5492 0.026 Uiso 1 1 calc R U . . .
C10 C 0.7478(3) 0.74485(18) 0.62101(13) 0.0162(5) Uani 1 1 d . . . . .
H4 H 0.7705 0.6927 0.6027 0.019 Uiso 1 1 calc R U . . .
C11 C 0.7983(3) 0.67600(16) 0.79679(12) 0.0127(5) Uani 1 1 d . . . . .
C12 C 0.7042(3) 0.74463(19) 0.88284(13) 0.0203(6) Uani 1 1 d . . . . .
H8 H 0.6893 0.7945 0.9053 0.024 Uiso 1 1 calc R U . . .
C13 C 0.6502(4) 0.6688(2) 0.90652(13) 0.0256(6) Uani 1 1 d . . . . .
H9 H 0.5995 0.6679 0.9441 0.031 Uiso 1 1 calc R U . . .
C14 C 0.6723(4) 0.59391(19) 0.87379(13) 0.0227(6) Uani 1 1 d . . . . .
H11 H 0.6373 0.5421 0.8891 0.027 Uiso 1 1 calc R U . . .
C15 C 0.7476(3) 0.59756(19) 0.81763(13) 0.0177(6) Uani 1 1 d . . . . .
H10 H 0.7635 0.5483 0.7945 0.021 Uiso 1 1 calc R U . . .
C16 C 0.8953(3) 0.97317(18) 0.90463(11) 0.0144(5) Uani 1 1 d . . . . .
C17 C 0.7607(3) 1.01751(18) 0.89511(12) 0.0164(5) Uani 1 1 d . . . . .
H13 H 0.7437 1.0682 0.9164 0.020 Uiso 1 1 calc R U . . .
C18 C 0.6520(3) 0.98787(17) 0.85466(11) 0.0147(5) Uani 1 1 d . . . . .
C19 C 0.5030(3) 1.0366(2) 0.85043(15) 0.0232(6) Uani 1 1 d . . . . .
C20 C 1.0011(3) 1.0064(2) 0.95538(13) 0.0200(6) Uani 1 1 d . . . . .
C21 C -0.1387(5) 0.3620(2) 0.93965(15) 0.0355(8) Uani 1 1 d . . . . .
C22 C -0.0565(4) 0.4306(2) 0.90238(13) 0.0237(7) Uani 1 1 d . . . . .
C23 C 0.0015(4) 0.5006(2) 0.93422(14) 0.0296(8) Uani 1 1 d . . . . .
H14 H -0.0056 0.5017 0.9770 0.036 Uiso 1 1 calc R U . . .
C24 C 0.0704(4) 0.5696(2) 0.90392(15) 0.0305(8) Uani 1 1 d . . . . .
C25 C 0.1209(6) 0.6455(3) 0.94360(19) 0.0494(11) Uani 1 1 d . . . . .
F2 F 0.2474(19) 0.6495(10) 0.9590(16) 0.082(9) Uani 0.44(4) 1 d . . P L 1
H16 H 0.972(6) 1.023(3) 0.772(2) 0.059(15) Uiso 1 1 d . . . . .
F2' F 0.2748(9) 0.6666(7) 0.9252(7) 0.060(3) Uani 0.56(4) 1 d . . P L 2
F12' F 0.136(2) 0.6318(5) 1.0001(3) 0.059(4) Uani 0.56(4) 1 d . . P L 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 2.028(2) . ?
Ni1 O3 2.051(2) . ?
Ni1 O2 2.0598(18) . ?
Ni1 N3 2.069(2) . ?
Ni1 N1 2.069(2) . ?
Ni1 N2 2.082(2) . ?
P1 O6 1.479(2) . ?
P1 C6 1.806(3) . ?
P1 C5 1.808(3) . ?
P1 C11 1.810(3) . ?
O1 H15 0.8200 . ?
O1 H16 0.88(5) . ?
O3 C18 1.262(3) . ?
F3 C19 1.317(4) . ?
F4 C19 1.331(4) . ?
F5 C19 1.340(4) . ?
F6 C20 1.340(4) . ?
F7 C20 1.327(4) . ?
F8 C20 1.305(4) . ?
F9 C21 1.327(4) . ?
F10 C21 1.317(4) . ?
F11 C21 1.342(5) . ?
F12 C25 1.511(19) . ?
N3 C12 1.341(4) . ?
N3 C11 1.355(3) . ?
O2 C16 1.252(3) . ?
F1 C25 1.300(5) . ?
O4 C22 1.245(4) . ?
O5 C24 1.236(4) . ?
N1 C1 1.333(4) . ?
N1 C5 1.348(4) . ?
N2 C7 1.335(4) . ?
N2 C6 1.347(3) . ?
C1 C2 1.387(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(4) . ?
C4 H12 0.9300 . ?
C6 C10 1.381(4) . ?
C7 C8 1.389(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(4) . ?
C8 H6 0.9300 . ?
C9 C10 1.389(4) . ?
C9 H5 0.9300 . ?
C10 H4 0.9300 . ?
C11 C15 1.383(4) . ?
C12 C13 1.379(4) . ?
C12 H8 0.9300 . ?
C13 C14 1.384(4) . ?
C13 H9 0.9300 . ?
C14 C15 1.389(4) . ?
C14 H11 0.9300 . ?
C15 H10 0.9300 . ?
C16 C17 1.392(4) . ?
C16 C20 1.535(4) . ?
C17 C18 1.381(4) . ?
C17 H13 0.9300 . ?
C18 C19 1.523(4) . ?
C21 C22 1.527(5) . ?
C22 C23 1.393(5) . ?
C23 C24 1.403(5) . ?
C23 H14 0.9300 . ?
C24 C25 1.533(5) . ?
C25 F2 1.168(11) . ?
C25 F12' 1.250(7) . ?
C25 F2' 1.455(11) . ?

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 Ni1 O3 86.89(8) . . ?
O1 Ni1 O2 87.64(8) . . ?
O3 Ni1 O2 87.24(7) . . ?
O1 Ni1 N3 176.01(9) . . ?
O3 Ni1 N3 90.63(9) . . ?
O2 Ni1 N3 95.36(8) . . ?
O1 Ni1 N1 91.97(9) . . ?
O3 Ni1 N1 176.33(8) . . ?
O2 Ni1 N1 89.23(8) . . ?
N3 Ni1 N1 90.70(9) . . ?
O1 Ni1 N2 86.79(8) . . ?
O3 Ni1 N2 89.74(8) . . ?
O2 Ni1 N2 173.80(8) . . ?
N3 Ni1 N2 90.08(9) . . ?
N1 Ni1 N2 93.67(9) . . ?
O6 P1 C6 112.05(12) . . ?
O6 P1 C5 115.15(13) . . ?
C6 P1 C5 104.91(13) . . ?
O6 P1 C11 114.26(12) . . ?
C6 P1 C11 104.74(12) . . ?
C5 P1 C11 104.71(12) . . ?
Ni1 O1 H15 109.5 . . ?
Ni1 O1 H16 135(3) . . ?
H15 O1 H16 104.4 . . ?
C18 O3 Ni1 121.9(2) . . ?
C12 N3 C11 117.8(2) . . ?
C12 N3 Ni1 120.94(19) . . ?
C11 N3 Ni1 121.27(18) . . ?
C16 O2 Ni1 122.53(17) . . ?
C1 N1 C5 117.6(2) . . ?
C1 N1 Ni1 120.49(19) . . ?
C5 N1 Ni1 121.83(18) . . ?
C7 N2 C6 118.1(2) . . ?
C7 N2 Ni1 120.11(18) . . ?
C6 N2 Ni1 121.51(18) . . ?
N1 C1 C2 122.6(3) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 118.1(3) . . ?
C3 C4 H12 121.0 . . ?
C5 C4 H12 121.0 . . ?
N1 C5 C4 123.4(3) . . ?
N1 C5 P1 116.2(2) . . ?
C4 C5 P1 120.4(2) . . ?
N2 C6 C10 123.4(2) . . ?
N2 C6 P1 116.26(19) . . ?
C10 C6 P1 120.3(2) . . ?
N2 C7 C8 122.0(3) . . ?
N2 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C9 C8 C7 119.6(3) . . ?
C9 C8 H6 120.2 . . ?
C7 C8 H6 120.2 . . ?
C8 C9 C10 118.9(3) . . ?
C8 C9 H5 120.5 . . ?
C10 C9 H5 120.5 . . ?
C6 C10 C9 118.0(3) . . ?
C6 C10 H4 121.0 . . ?
C9 C10 H4 121.0 . . ?
N3 C11 C15 122.8(2) . . ?
N3 C11 P1 116.60(19) . . ?
C15 C11 P1 120.6(2) . . ?
N3 C12 C13 122.7(3) . . ?
N3 C12 H8 118.6 . . ?
C13 C12 H8 118.6 . . ?
C12 C13 C14 119.3(3) . . ?
C12 C13 H9 120.3 . . ?
C14 C13 H9 120.4 . . ?
C13 C14 C15 118.9(3) . . ?
C13 C14 H11 120.6 . . ?
C15 C14 H11 120.6 . . ?
C11 C15 C14 118.6(3) . . ?
C11 C15 H10 120.7 . . ?
C14 C15 H10 120.7 . . ?
O2 C16 C17 128.6(2) . . ?
O2 C16 C20 114.2(2) . . ?
C17 C16 C20 117.2(2) . . ?
C18 C17 C16 121.4(3) . . ?
C18 C17 H13 119.3 . . ?
C16 C17 H13 119.3 . . ?
O3 C18 C17 129.1(3) . . ?
O3 C18 C19 112.7(3) . . ?
C17 C18 C19 118.1(2) . . ?
F3 C19 F4 108.5(3) . . ?
F3 C19 F5 107.0(3) . . ?
F4 C19 F5 105.4(3) . . ?
F3 C19 C18 111.4(3) . . ?
F4 C19 C18 113.5(3) . . ?
F5 C19 C18 110.6(2) . . ?
F8 C20 F7 108.0(3) . . ?
F8 C20 F6 107.5(3) . . ?
F7 C20 F6 106.0(2) . . ?
F8 C20 C16 112.5(2) . . ?
F7 C20 C16 110.3(3) . . ?
F6 C20 C16 112.3(2) . . ?
F10 C21 F9 107.1(3) . . ?
F10 C21 F11 104.6(3) . . ?
F9 C21 F11 105.3(4) . . ?
F10 C21 C22 115.7(3) . . ?
F9 C21 C22 112.6(3) . . ?
F11 C21 C22 110.7(3) . . ?
O4 C22 C23 128.9(3) . . ?
O4 C22 C21 113.3(3) . . ?
C23 C22 C21 117.7(3) . . ?
C22 C23 C24 122.2(3) . . ?
C22 C23 H14 118.9 . . ?
C24 C23 H14 118.9 . . ?
O5 C24 C23 128.9(3) . . ?
O5 C24 C25 113.7(3) . . ?
C23 C24 C25 117.4(3) . . ?
F2 C25 F1 118.1(10) . . ?
F12' C25 F1 117.0(7) . . ?
F12' C25 F2' 102.1(6) . . ?
F1 C25 F2' 99.4(6) . . ?
F2 C25 F12 101.8(10) . . ?
F1 C25 F12 92.2(11) . . ?
F2 C25 C24 118.7(8) . . ?
F12' C25 C24 116.6(5) . . ?
F1 C25 C24 111.9(3) . . ?
F2' C25 C24 107.1(5) . . ?
F12 C25 C24 109.4(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.3(4) . . . . ?
Ni1 N1 C1 C2 -177.0(2) . . . . ?
N1 C1 C2 C3 0.7(5) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C1 N1 C5 C4 0.0(4) . . . . ?
Ni1 N1 C5 C4 176.7(2) . . . . ?
C1 N1 C5 P1 -179.9(2) . . . . ?
Ni1 N1 C5 P1 -3.3(3) . . . . ?
C3 C4 C5 N1 -0.2(5) . . . . ?
C3 C4 C5 P1 179.8(2) . . . . ?
O6 P1 C5 N1 -179.30(18) . . . . ?
C6 P1 C5 N1 57.1(2) . . . . ?
C11 P1 C5 N1 -53.0(2) . . . . ?
O6 P1 C5 C4 0.8(3) . . . . ?
C6 P1 C5 C4 -122.9(3) . . . . ?
C11 P1 C5 C4 127.1(2) . . . . ?
C7 N2 C6 C10 0.1(4) . . . . ?
Ni1 N2 C6 C10 -173.5(2) . . . . ?
C7 N2 C6 P1 179.9(2) . . . . ?
Ni1 N2 C6 P1 6.3(3) . . . . ?
O6 P1 C6 N2 175.64(19) . . . . ?
C5 P1 C6 N2 -58.7(2) . . . . ?
C11 P1 C6 N2 51.2(2) . . . . ?
O6 P1 C6 C10 -4.6(3) . . . . ?
C5 P1 C6 C10 121.0(2) . . . . ?
C11 P1 C6 C10 -129.0(2) . . . . ?
C6 N2 C7 C8 -0.3(4) . . . . ?
Ni1 N2 C7 C8 173.4(2) . . . . ?
N2 C7 C8 C9 0.5(5) . . . . ?
C7 C8 C9 C10 -0.5(5) . . . . ?
N2 C6 C10 C9 -0.2(4) . . . . ?
P1 C6 C10 C9 -179.9(2) . . . . ?
C8 C9 C10 C6 0.4(4) . . . . ?
C12 N3 C11 C15 0.1(4) . . . . ?
Ni1 N3 C11 C15 -179.8(2) . . . . ?
C12 N3 C11 P1 -179.5(2) . . . . ?
Ni1 N3 C11 P1 0.6(3) . . . . ?
O6 P1 C11 N3 -178.53(18) . . . . ?
C6 P1 C11 N3 -55.6(2) . . . . ?
C5 P1 C11 N3 54.6(2) . . . . ?
O6 P1 C11 C15 1.9(3) . . . . ?
C6 P1 C11 C15 124.8(2) . . . . ?
C5 P1 C11 C15 -125.0(2) . . . . ?
C11 N3 C12 C13 -0.2(4) . . . . ?
Ni1 N3 C12 C13 179.7(2) . . . . ?
N3 C12 C13 C14 0.4(5) . . . . ?
C12 C13 C14 C15 -0.4(5) . . . . ?
N3 C11 C15 C14 -0.2(4) . . . . ?
P1 C11 C15 C14 179.4(2) . . . . ?
C13 C14 C15 C11 0.3(4) . . . . ?
Ni1 O2 C16 C17 18.7(4) . . . . ?
Ni1 O2 C16 C20 -163.85(18) . . . . ?
O2 C16 C17 C18 3.6(5) . . . . ?
C20 C16 C17 C18 -173.8(3) . . . . ?
Ni1 O3 C18 C17 -20.1(4) . . . . ?
Ni1 O3 C18 C19 161.51(18) . . . . ?
C16 C17 C18 O3 -2.8(5) . . . . ?
C16 C17 C18 C19 175.5(3) . . . . ?
O3 C18 C19 F3 68.0(3) . . . . ?
C17 C18 C19 F3 -110.5(3) . . . . ?
O3 C18 C19 F4 -169.1(3) . . . . ?
C17 C18 C19 F4 12.3(4) . . . . ?
O3 C18 C19 F5 -50.8(3) . . . . ?
C17 C18 C19 F5 130.6(3) . . . . ?
O2 C16 C20 F8 30.5(4) . . . . ?
C17 C16 C20 F8 -151.7(3) . . . . ?
O2 C16 C20 F7 -90.1(3) . . . . ?
C17 C16 C20 F7 87.6(3) . . . . ?
O2 C16 C20 F6 152.0(2) . . . . ?
C17 C16 C20 F6 -30.3(4) . . . . ?
F10 C21 C22 O4 170.6(3) . . . . ?
F9 C21 C22 O4 46.9(4) . . . . ?
F11 C21 C22 O4 -70.7(4) . . . . ?
F10 C21 C22 C23 -11.3(5) . . . . ?
F9 C21 C22 C23 -135.0(3) . . . . ?
F11 C21 C22 C23 107.5(4) . . . . ?
O4 C22 C23 C24 2.0(6) . . . . ?
C21 C22 C23 C24 -175.9(3) . . . . ?
C22 C23 C24 O5 -1.7(6) . . . . ?
C22 C23 C24 C25 176.3(3) . . . . ?
O5 C24 C25 F2 -84(2) . . . . ?
C23 C24 C25 F2 97(2) . . . . ?
O5 C24 C25 F12' -162.8(11) . . . . ?
C23 C24 C25 F12' 19.0(12) . . . . ?
O5 C24 C25 F1 58.7(5) . . . . ?
C23 C24 C25 F1 -119.5(4) . . . . ?
O5 C24 C25 F2' -49.3(7) . . . . ?
C23 C24 C25 F2' 132.5(7) . . . . ?
O5 C24 C25 F12 159.5(14) . . . . ?
C23 C24 C25 F12 -18.7(14) . . . . ?

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
O1 H16 O6 0.88(5) 1.80(5) 2.666(3) 171(5) 3_756
C12 H8 F12' 0.93 2.40 3.248(6) 151.5 2_567
C12 H8 F12 0.93 2.55 3.340(12) 142.8 2_567
C8 H6 F7 0.93 2.53 3.387(3) 154.2 4_674
C2 H2 O3 0.93 2.49 3.420(4) 177.4 1_655
C1 H1 O2 0.93 2.60 3.047(3) 110.3 .
O1 H15 O5 0.82 2.30 2.811(3) 121.3 3_656
O1 H15 O4 0.82 2.01 2.772(3) 154.0 3_656
O1 H16 O6 0.88(5) 1.80(5) 2.666(3) 171(5) 3_756
C8 H6 F7 0.93 2.53 3.387(3) 154.2 4_674
C2 H2 O3 0.93 2.49 3.420(4) 177.4 1_655
C1 H1 O2 0.93 2.60 3.047(3) 110.3 .
O1 H16 O6 0.88(5) 1.80(5) 2.666(3) 171(5) 3_756
C12 H8 F12 0.93 2.55 3.340(12) 142.8 2_567
C8 H6 F7 0.93 2.53 3.387(3) 154.2 4_674
C2 H2 O3 0.93 2.49 3.420(4) 177.4 1_655
C1 H1 O2 0.93 2.60 3.047(3) 110.3 .
O1 H15 O5 0.82 2.30 2.811(3) 121.3 3_656
O1 H15 O4 0.82 2.01 2.772(3) 154.0 3_656
C12 H8 F12 0.93 2.55 3.340(12) 142.8 2_567
C8 H6 F7 0.93 2.53 3.387(3) 154.2 4_674
C2 H2 O3 0.93 2.49 3.420(4) 177.4 1_655
C1 H1 O2 0.93 2.60 3.047(3) 110.3 .
O1 H15 O5 0.82 2.30 2.811(3) 121.3 3_656
O1 H15 O4 0.82 2.01 2.772(3) 154.0 3_656
C12 H8 F12 0.93 2.55 3.340(12) 142.8 2_567
C8 H6 F7 0.93 2.53 3.387(3) 154.2 4_674
C2 H2 O3 0.93 2.49 3.420(4) 177.4 1_655
C1 H1 O2 0.93 2.60 3.047(3) 110.3 .
O1 H16 O6 0.88(5) 1.80(5) 2.666(3) 171(5) 3_756
C12 H8 F12 0.93 2.55 3.340(12) 142.8 2_567
C8 H6 F7 0.93 2.53 3.387(3) 154.2 4_674
C2 H2 O3 0.93 2.49 3.420(4) 177.4 1_655
C1 H1 O2 0.93 2.60 3.047(3) 110.3 .
O1 H16 O6 0.88(5) 1.80(5) 2.666(3) 171(5) 3_756
C8 H6 F7 0.93 2.53 3.387(3) 154.2 4_674
C2 H2 O3 0.93 2.49 3.420(4) 177.4 1_655
C1 H1 O2 0.93 2.60 3.047(3) 110.3 .
O1 H16 O6 0.88(5) 1.80(5) 2.666(3) 171(5) 3_756
C12 H8 F12 0.93 2.55 3.340(12) 142.8 2_567
C8 H6 F7 0.93 2.53 3.387(3) 154.2 4_674
C2 H2 O3 0.93 2.49 3.420(4) 177.4 1_655
C1 H1 O2 0.93 2.60 3.047(3) 110.3 .
C12 H8 F12 0.93 2.55 3.340(12) 142.8 2_567
C8 H6 F7 0.93 2.53 3.387(3) 154.2 4_674
C2 H2 O3 0.93 2.49 3.420(4) 177.4 1_655
C1 H1 O2 0.93 2.60 3.047(3) 110.3 .
C8 H6 F7 0.93 2.53 3.387(3) 154.2 4_674
C1 H1 O2 0.93 2.60 3.047(3) 110.3 .
C1 H1 O2 0.93 2.60 3.047(3) 110.3 .
C2 H2 O3 0.93 2.49 3.420(4) 177.4 1_655
C8 H6 F7 0.93 2.53 3.387(3) 154.2 4_674
O1 H16 O6 0.88(5) 1.80(5) 2.666(3) 171(5) 3_756
C1 H1 O2 0.93 2.60 3.047(3) 110.3 .
C2 H2 O3 0.93 2.49 3.420(4) 177.4 1_655
C8 H6 F7 0.93 2.53 3.387(3) 154.2 4_674
C12 H8 F12 0.93 2.55 3.340(12) 142.8 2_567
O1 H15 O4 0.82 2.01 2.772(3) 154.0 3_656
O1 H15 O5 0.82 2.30 2.811(3) 121.3 3_656
C1 H1 O2 0.93 2.60 3.047(3) 110.3 .
C2 H2 O3 0.93 2.49 3.420(4) 177.4 1_655
C8 H6 F7 0.93 2.53 3.387(3) 154.2 4_674
C12 H8 F12 0.93 2.55 3.340(12) 142.8 2_567
O1 H16 O6 0.88(5) 1.80(5) 2.666(3) 171(5) 3_756
O1 H15 O4 0.82 2.01 2.772(3) 154.0 3_656
O1 H15 O5 0.82 2.30 2.811(3) 121.3 3_656
C1 H1 O2 0.93 2.60 3.047(3) 110.3 .
C2 H2 O3 0.93 2.49 3.420(4) 177.4 1_655
C8 H6 F7 0.93 2.53 3.387(3) 154.2 4_674
C12 H8 F12 0.93 2.55 3.340(12) 142.8 2_567
C12 H8 F12' 0.93 2.40 3.248(6) 151.5 2_567
O1 H16 O6 0.88(5) 1.80(5) 2.666(3) 171(5) 3_756

_refine_diff_density_max         0.852
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.068

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_mo_Artemev_Mn_181114_0m
_database_code_depnum_ccdc_archive 'CCDC 1035512'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
'complex of tris(2-pyridyl)phosphine with manganese hexafluoroacetylacetonate'
_chemical_name_common            ?
_chemical_melting_point          490
_chemical_formula_moiety         
'2(C15 H3 F18 Mn O6), C30 H24 Mn N6 P2, 2(C3 H6 O)'
_chemical_formula_sum            'C66 H42 F36 Mn3 N6 O14 P2'
_chemical_formula_weight         2053.82

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'
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'
Mn Mn 0.3368 0.7283 '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                   10.5909(7)
_cell_length_b                   12.6726(9)
_cell_length_c                   16.6408(11)
_cell_angle_alpha                80.785(3)
_cell_angle_beta                 79.387(3)
_cell_angle_gamma                65.580(3)
_cell_volume                     1990.0(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prizm
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_F_000             1021
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.658
_shelx_estimated_absorpt_T_min   0.644
_shelx_estimated_absorpt_T_max   0.761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.624
_exptl_absorpt_correction_T_max  0.749
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            123437
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.263
_diffrn_reflns_theta_max         30.113
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             11664
_reflns_number_gt                8533
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0336P)²+1.7612P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11664
_refine_ls_number_parameters     663
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0848
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
Mn1 Mn 0.5000 0.5000 0.5000 0.01447(8) Uani 1 2 d S . P A 1
O2 O 0.90915(15) 0.98018(12) 0.73964(8) 0.0241(3) Uani 1 1 d . . . B 1
Mn2 Mn 0.84512(3) 0.83861(3) 0.78469(2) 0.01943(7) Uani 1 1 d . . . B 1
P1 P 0.67099(5) 0.33121(4) 0.33062(3) 0.01705(10) Uani 1 1 d . . . A 1
O3 O 1.04569(14) 0.76448(11) 0.83116(8) 0.0209(3) Uani 1 1 d . . . B 1
F1 F 1.01746(13) 0.59508(10) 0.56560(7) 0.0292(3) Uani 1 1 d . . . C 1
F2 F 0.7412(2) 0.88074(19) 1.11070(9) 0.0710(6) Uani 1 1 d . . . D 1
F3 F 0.6079(2) 1.02514(18) 1.03857(12) 0.0722(6) Uani 1 1 d . . . E 1
F4 F 0.8280(2) 0.98448(19) 1.02356(11) 0.0709(6) Uani 1 1 d . . . F 1
F5 F 0.69278(19) 0.53803(15) 0.95034(11) 0.0584(4) Uani 1 1 d . . . G 1
F6 F 0.9122(2) 0.46883(14) 0.91328(12) 0.0688(5) Uani 1 1 d . . . H 1
F7 F 0.8330(2) 0.51488(17) 1.03614(10) 0.0760(6) Uani 1 1 d . . . I 1
F8 F 1.32978(14) 0.78918(12) 0.89009(9) 0.0419(3) Uani 1 1 d . . . J 1
F9 F 1.17560(16) 0.74586(14) 0.97613(8) 0.0486(4) Uani 1 1 d . . . K 1
F10 F 1.29637(13) 0.63710(10) 0.88010(8) 0.0334(3) Uani 1 1 d . . . L 1
F11 F 0.86745(15) 1.20305(11) 0.73001(11) 0.0498(4) Uani 1 1 d . . . M 1
F12 F 1.05874(17) 1.16230(12) 0.77726(10) 0.0485(4) Uani 1 1 d . . . N 1
F13 F 1.06339(18) 1.12205(13) 0.65737(9) 0.0526(4) Uani 1 1 d . . . O 1
O1 O 0.53716(18) 0.36287(14) 0.75319(10) 0.0373(4) Uani 1 1 d . . . P 1
N1 N 0.34243(15) 0.47314(13) 0.60435(9) 0.0169(3) Uani 1 1 d . . . A 1
C1 C 0.30980(19) 0.38049(16) 0.60886(12) 0.0190(4) Uani 1 1 d . . . A 1
C2 C 0.2237(2) 0.35217(17) 0.67361(12) 0.0218(4) Uani 1 1 d . . . A 1
C3 C 0.1669(2) 0.42288(17) 0.73703(12) 0.0226(4) Uani 1 1 d . . . A 1
C4 C 0.1986(2) 0.51962(17) 0.73365(12) 0.0197(4) Uani 1 1 d . . . A 1
C5 C 0.28713(18) 0.54206(15) 0.66687(11) 0.0163(3) Uani 1 1 d . . . A 1
C6 C 0.29986(19) 0.74466(15) 0.56608(11) 0.0174(3) Uani 1 1 d . . . A 1
C7 C 0.2123(2) 0.86189(17) 0.56331(13) 0.0227(4) Uani 1 1 d . . . A 1
C8 C 0.1877(2) 0.92584(17) 0.48803(14) 0.0259(4) Uani 1 1 d . . . A 1
C9 C 0.2504(2) 0.87134(17) 0.41726(13) 0.0245(4) Uani 1 1 d . . . A 1
C10 C 0.3361(2) 0.75400(17) 0.42412(12) 0.0205(4) Uani 1 1 d . . . A 1
N2 N 0.36196(16) 0.69059(13) 0.49668(9) 0.0176(3) Uani 1 1 d . . . A 1
C12 C 0.47861(19) 0.40110(15) 0.34006(11) 0.0169(3) Uani 1 1 d . . . A 1
C13 C 0.4158(2) 0.38369(17) 0.27988(12) 0.0214(4) Uani 1 1 d . . . A 1
C14 C 0.2717(2) 0.43976(18) 0.28048(13) 0.0249(4) Uani 1 1 d . . . A 1
C15 C 0.1950(2) 0.51154(18) 0.34166(13) 0.0233(4) Uani 1 1 d . . . A 1
C16 C 0.2639(2) 0.52262(17) 0.40083(12) 0.0210(4) Uani 1 1 d . . . A 1
N3 N 0.40268(16) 0.46872(13) 0.40127(9) 0.0172(3) Uani 1 1 d . . . A 1
O6 O 0.64927(14) 0.92445(13) 0.73394(9) 0.0260(3) Uani 1 1 d . . . B 1
C19 C 0.6191(2) 0.91073(16) 0.66860(12) 0.0208(4) Uani 1 1 d . . . B 1
C20 C 0.4658(2) 0.98366(19) 0.65483(14) 0.0297(5) Uani 1 1 d . . . B 1
F17 F 0.3839(3) 0.9392(6) 0.7048(4) 0.071(3) Uani 0.566(13) 1 d . . P B 1
F16 F 0.4387(5) 0.9803(7) 0.5813(3) 0.079(3) Uani 0.566(13) 1 d . . P B 1
F18 F 0.4275(5) 1.0891(4) 0.6669(7) 0.088(4) Uani 0.566(13) 1 d . . P B 1
C24 C 0.7051(2) 0.84010(17) 0.60735(12) 0.0206(4) Uani 1 1 d . . . . .
C25 C 0.84572(19) 0.77150(16) 0.61393(11) 0.0174(3) Uani 1 1 d . . . . .
O7 O 0.91397(14) 0.75958(12) 0.67099(8) 0.0233(3) Uani 1 1 d . . . . .
C27 C 0.9347(2) 0.70352(17) 0.54124(11) 0.0204(4) Uani 1 1 d . . . . .
F14 F 1.01808(13) 0.75478(10) 0.49961(7) 0.0287(3) Uani 1 1 d . . . . .
F15 F 0.86028(13) 0.69575(12) 0.48735(8) 0.0358(3) Uani 1 1 d . . . . .
O5 O 0.80790(16) 0.69275(13) 0.85255(8) 0.0271(3) Uani 1 1 d . . . . .
C31 C 0.7999(2) 0.6715(2) 0.92887(13) 0.0297(5) Uani 1 1 d . . . . .
C32 C 0.7792(3) 0.7453(2) 0.98807(14) 0.0353(5) Uani 1 1 d . . . . .
C33 C 0.7580(2) 0.8619(2) 0.96714(13) 0.0312(5) Uani 1 1 d . . . . .
C34 C 0.7329(3) 0.9386(3) 1.03639(16) 0.0479(7) Uani 1 1 d . . . . .
O4 O 0.75586(16) 0.91590(13) 0.89784(9) 0.0293(3) Uani 1 1 d . . . . .
C36 C 0.8109(3) 0.5467(2) 0.95825(15) 0.0443(6) Uani 1 1 d . . . . .
C37 C 1.1154(2) 0.81794(16) 0.84303(11) 0.0193(4) Uani 1 1 d . . . . .
C38 C 1.0990(2) 0.93238(17) 0.81536(12) 0.0216(4) Uani 1 1 d . . . . .
C39 C 1.2311(2) 0.74725(18) 0.89769(13) 0.0270(4) Uani 1 1 d . . . . .
C40 C 0.9961(2) 1.12381(18) 0.73368(13) 0.0263(4) Uani 1 1 d . . . . .
C41 C 0.5577(2) 0.30112(19) 0.81644(14) 0.0292(5) Uani 1 1 d . . . . .
C42 C 0.5949(4) 0.3372(4) 0.88665(19) 0.0767(11) Uani 1 1 d . . . . .
H42A H 0.6073 0.2775 0.9316 0.115 Uiso 1 1 calc R U . . .
H42B H 0.5212 0.4084 0.9037 0.115 Uiso 1 1 calc R U . . .
H42C H 0.6803 0.3489 0.8700 0.115 Uiso 1 1 calc R U . . .
C43 C 0.5468(4) 0.1870(3) 0.8263(2) 0.0706(10) Uani 1 1 d . . . . .
H43A H 0.5149 0.1777 0.7786 0.106 Uiso 1 1 calc R U . . .
H43B H 0.4815 0.1832 0.8739 0.106 Uiso 1 1 calc R U . . .
H43C H 0.6369 0.1260 0.8330 0.106 Uiso 1 1 calc R U . . .
C35 C 0.9979(2) 1.00307(16) 0.76610(11) 0.0199(4) Uani 1 1 d . . . . .
H1 H 0.672(2) 0.8396(19) 0.5600(14) 0.025(6) Uiso 1 1 d . . . . .
H3 H 1.158(2) 0.9629(19) 0.8298(13) 0.021(5) Uiso 1 1 d . . . . .
H20 H 0.105(2) 0.4052(19) 0.7841(14) 0.023(6) Uiso 1 1 d . . . . .
H6 H 0.205(2) 0.284(2) 0.6736(13) 0.024(6) Uiso 1 1 d . . . . .
H7 H 0.165(2) 0.568(2) 0.7757(14) 0.023(6) Uiso 1 1 d . . . . .
H8 H 0.351(2) 0.3336(18) 0.5647(13) 0.016(5) Uiso 1 1 d . . . . .
H9 H 0.168(3) 0.895(2) 0.6131(15) 0.030(6) Uiso 1 1 d . . . . .
H10 H 0.130(2) 1.003(2) 0.4869(14) 0.025(6) Uiso 1 1 d . . . . .
H11 H 0.235(3) 0.911(2) 0.3632(15) 0.032(6) Uiso 1 1 d . . . . .
H12 H 0.382(2) 0.7150(18) 0.3772(13) 0.017(5) Uiso 1 1 d . . . . .
H13 H 0.216(2) 0.5695(19) 0.4433(14) 0.022(6) Uiso 1 1 d . . . . .
H14 H 0.095(3) 0.553(2) 0.3435(14) 0.029(6) Uiso 1 1 d . . . . .
H15 H 0.228(2) 0.4299(19) 0.2384(14) 0.024(6) Uiso 1 1 d . . . . .
H16 H 0.472(2) 0.337(2) 0.2379(14) 0.024(6) Uiso 1 1 d . . . . .
H25 H 0.781(3) 0.716(2) 1.0430(17) 0.043(7) Uiso 1 1 d . . . . .
F16' F 0.4147(6) 0.9354(6) 0.6172(8) 0.085(5) Uani 0.434(13) 1 d . . P B 2
F17' F 0.4560(5) 1.0824(6) 0.6066(6) 0.064(3) Uani 0.434(13) 1 d . . P B 2
F18' F 0.3829(4) 1.0212(9) 0.7214(3) 0.073(4) Uani 0.434(13) 1 d . . P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 N2 2.2452(15) 2_666 ?
Mn1 N2 2.2453(15) . ?
Mn1 N3 2.2558(15) . ?
Mn1 N3 2.2559(15) 2_666 ?
Mn1 N1 2.2647(15) . ?
Mn1 N1 2.2647(15) 2_666 ?
O2 C35 1.258(2) . ?
O2 Mn2 2.1513(14) . ?
Mn2 O4 2.1372(14) . ?
Mn2 O7 2.1469(14) . ?
Mn2 O5 2.1488(14) . ?
Mn2 O6 2.1643(14) . ?
Mn2 O3 2.1714(13) . ?
P1 C5 1.8425(18) 2_666 ?
P1 C12 1.8425(19) . ?
P1 C6 1.8426(19) 2_666 ?
O3 C37 1.247(2) . ?
F1 C27 1.333(2) . ?
F2 C34 1.330(3) . ?
F3 C34 1.324(4) . ?
F4 C34 1.328(3) . ?
F5 C36 1.332(3) . ?
F6 C36 1.323(3) . ?
F7 C36 1.328(3) . ?
F8 C39 1.334(2) . ?
F9 C39 1.330(3) . ?
F10 C39 1.331(2) . ?
F11 C40 1.322(2) . ?
F12 C40 1.327(2) . ?
F13 C40 1.336(3) . ?
O1 C41 1.203(3) . ?
N1 C1 1.342(2) . ?
N1 C5 1.353(2) . ?
C1 C2 1.381(3) . ?
C1 H8 0.94(2) . ?
C2 C3 1.379(3) . ?
C2 H6 0.97(2) . ?
C3 C4 1.389(3) . ?
C3 H20 0.98(2) . ?
C4 C5 1.389(3) . ?
C4 H7 0.93(2) . ?
C5 P1 1.8426(18) 2_666 ?
C6 N2 1.355(2) . ?
C6 C7 1.387(3) . ?
C6 P1 1.8425(19) 2_666 ?
C7 C8 1.384(3) . ?
C7 H9 0.94(2) . ?
C8 C9 1.378(3) . ?
C8 H10 0.91(2) . ?
C9 C10 1.384(3) . ?
C9 H11 0.96(2) . ?
C10 N2 1.345(2) . ?
C10 H12 0.93(2) . ?
C12 N3 1.352(2) . ?
C12 C13 1.390(3) . ?
C13 C14 1.390(3) . ?
C13 H16 0.94(2) . ?
C14 C15 1.380(3) . ?
C14 H15 0.95(2) . ?
C15 C16 1.384(3) . ?
C15 H14 0.97(2) . ?
C16 N3 1.341(2) . ?
C16 H13 0.93(2) . ?
O6 C19 1.245(2) . ?
C19 C24 1.395(3) . ?
C19 C20 1.540(3) . ?
C20 F18 1.265(4) . ?
C20 F16 1.318(5) . ?
C20 F17 1.322(4) . ?
C24 C25 1.395(3) . ?
C24 H1 0.92(2) . ?
C25 O7 1.250(2) . ?
C25 C27 1.528(3) . ?
C27 F14 1.337(2) . ?
C27 F15 1.337(2) . ?
O5 C31 1.250(2) . ?
C31 C32 1.392(3) . ?
C31 C36 1.541(3) . ?
C32 C33 1.395(3) . ?
C32 H25 0.93(3) . ?
C33 O4 1.242(3) . ?
C33 C34 1.541(3) . ?
C37 C38 1.397(3) . ?
C37 C39 1.540(3) . ?
C38 C35 1.384(3) . ?
C38 H3 0.94(2) . ?
C40 C35 1.532(3) . ?
C41 C43 1.479(4) . ?
C41 C42 1.489(4) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Mn1 N2 180.0 2_666 . ?
N2 Mn1 N3 86.28(5) 2_666 . ?
N2 Mn1 N3 93.72(5) . . ?
N2 Mn1 N3 93.72(5) 2_666 2_666 ?
N2 Mn1 N3 86.28(5) . 2_666 ?
N3 Mn1 N3 180.00(4) . 2_666 ?
N2 Mn1 N1 93.21(5) 2_666 . ?
N2 Mn1 N1 86.79(5) . . ?
N3 Mn1 N1 94.77(5) . . ?
N3 Mn1 N1 85.23(5) 2_666 . ?
N2 Mn1 N1 86.79(5) 2_666 2_666 ?
N2 Mn1 N1 93.21(5) . 2_666 ?
N3 Mn1 N1 85.23(5) . 2_666 ?
N3 Mn1 N1 94.77(5) 2_666 2_666 ?
N1 Mn1 N1 180.0 . 2_666 ?
C35 O2 Mn2 126.88(12) . . ?
O4 Mn2 O7 173.90(6) . . ?
O4 Mn2 O5 83.28(6) . . ?
O7 Mn2 O5 93.71(5) . . ?
O4 Mn2 O2 89.17(6) . . ?
O7 Mn2 O2 94.77(5) . . ?
O5 Mn2 O2 166.70(5) . . ?
O4 Mn2 O6 92.55(6) . . ?
O7 Mn2 O6 82.61(5) . . ?
O5 Mn2 O6 98.19(6) . . ?
O2 Mn2 O6 93.05(5) . . ?
O4 Mn2 O3 87.59(5) . . ?
O7 Mn2 O3 97.54(5) . . ?
O5 Mn2 O3 86.45(5) . . ?
O2 Mn2 O3 82.30(5) . . ?
O6 Mn2 O3 175.35(5) . . ?
C5 P1 C12 100.55(8) 2_666 . ?
C5 P1 C6 102.39(8) 2_666 2_666 ?
C12 P1 C6 101.97(8) . 2_666 ?
C37 O3 Mn2 127.03(12) . . ?
C1 N1 C5 117.72(16) . . ?
C1 N1 Mn1 119.60(12) . . ?
C5 N1 Mn1 122.47(12) . . ?
N1 C1 C2 123.52(18) . . ?
N1 C1 H8 115.5(13) . . ?
C2 C1 H8 121.0(13) . . ?
C3 C2 C1 118.64(18) . . ?
C3 C2 H6 121.6(13) . . ?
C1 C2 H6 119.7(13) . . ?
C2 C3 C4 118.96(18) . . ?
C2 C3 H20 120.7(13) . . ?
C4 C3 H20 120.3(13) . . ?
C3 C4 C5 119.19(18) . . ?
C3 C4 H7 121.6(14) . . ?
C5 C4 H7 119.2(14) . . ?
N1 C5 C4 121.97(16) . . ?
N1 C5 P1 121.73(13) . 2_666 ?
C4 C5 P1 116.28(14) . 2_666 ?
N2 C6 C7 121.63(17) . . ?
N2 C6 P1 122.46(13) . 2_666 ?
C7 C6 P1 115.89(15) . 2_666 ?
C8 C7 C6 119.49(19) . . ?
C8 C7 H9 121.9(15) . . ?
C6 C7 H9 118.6(15) . . ?
C9 C8 C7 119.15(19) . . ?
C9 C8 H10 122.0(14) . . ?
C7 C8 H10 118.8(14) . . ?
C8 C9 C10 118.60(19) . . ?
C8 C9 H11 122.8(15) . . ?
C10 C9 H11 118.6(15) . . ?
N2 C10 C9 123.12(19) . . ?
N2 C10 H12 116.3(13) . . ?
C9 C10 H12 120.6(13) . . ?
C10 N2 C6 118.00(16) . . ?
C10 N2 Mn1 119.85(13) . . ?
C6 N2 Mn1 122.12(12) . . ?
N3 C12 C13 121.66(17) . . ?
N3 C12 P1 121.51(13) . . ?
C13 C12 P1 116.80(14) . . ?
C12 C13 C14 119.73(19) . . ?
C12 C13 H16 119.4(14) . . ?
C14 C13 H16 120.8(14) . . ?
C15 C14 C13 118.42(18) . . ?
C15 C14 H15 121.5(14) . . ?
C13 C14 H15 120.1(14) . . ?
C14 C15 C16 118.81(19) . . ?
C14 C15 H14 121.0(14) . . ?
C16 C15 H14 120.2(14) . . ?
N3 C16 C15 123.45(19) . . ?
N3 C16 H13 115.3(14) . . ?
C15 C16 H13 121.2(14) . . ?
C16 N3 C12 117.88(16) . . ?
C16 N3 Mn1 119.13(12) . . ?
C12 N3 Mn1 122.94(12) . . ?
C19 O6 Mn2 129.04(13) . . ?
O6 C19 C24 128.78(18) . . ?
O6 C19 C20 114.22(18) . . ?
C24 C19 C20 117.00(17) . . ?
F18 C20 F16 108.2(4) . . ?
F18 C20 F17 109.3(4) . . ?
F16 C20 F17 103.5(3) . . ?
F18 C20 C19 112.1(2) . . ?
F16 C20 C19 114.0(3) . . ?
F17 C20 C19 109.4(2) . . ?
C25 C24 C19 121.25(17) . . ?
C25 C24 H1 117.7(14) . . ?
C19 C24 H1 121.0(14) . . ?
O7 C25 C24 129.08(18) . . ?
O7 C25 C27 113.17(16) . . ?
C24 C25 C27 117.70(16) . . ?
C25 O7 Mn2 129.12(12) . . ?
F1 C27 F14 106.85(15) . . ?
F1 C27 F15 106.96(15) . . ?
F14 C27 F15 106.71(15) . . ?
F1 C27 C25 111.81(15) . . ?
F14 C27 C25 110.08(15) . . ?
F15 C27 C25 114.04(15) . . ?
C31 O5 Mn2 124.96(13) . . ?
O5 C31 C32 128.8(2) . . ?
O5 C31 C36 113.10(19) . . ?
C32 C31 C36 118.1(2) . . ?
C31 C32 C33 121.7(2) . . ?
C31 C32 H25 119.1(17) . . ?
C33 C32 H25 119.1(17) . . ?
O4 C33 C32 128.5(2) . . ?
O4 C33 C34 112.9(2) . . ?
C32 C33 C34 118.6(2) . . ?
F3 C34 F4 107.9(3) . . ?
F3 C34 F2 107.2(2) . . ?
F4 C34 F2 107.1(2) . . ?
F3 C34 C33 111.0(2) . . ?
F4 C34 C33 109.7(2) . . ?
F2 C34 C33 113.6(2) . . ?
C33 O4 Mn2 125.42(15) . . ?
F6 C36 F7 107.5(2) . . ?
F6 C36 F5 106.2(2) . . ?
F7 C36 F5 107.7(2) . . ?
F6 C36 C31 112.0(2) . . ?
F7 C36 C31 113.5(2) . . ?
F5 C36 C31 109.5(2) . . ?
O3 C37 C38 128.49(17) . . ?
O3 C37 C39 114.16(16) . . ?
C38 C37 C39 117.32(17) . . ?
C35 C38 C37 121.74(18) . . ?
C35 C38 H3 118.4(13) . . ?
C37 C38 H3 119.9(13) . . ?
F9 C39 F10 107.19(17) . . ?
F9 C39 F8 108.02(17) . . ?
F10 C39 F8 106.44(17) . . ?
F9 C39 C37 109.93(17) . . ?
F10 C39 C37 111.67(16) . . ?
F8 C39 C37 113.32(17) . . ?
F11 C40 F12 107.76(18) . . ?
F11 C40 F13 106.47(18) . . ?
F12 C40 F13 105.81(18) . . ?
F11 C40 C35 112.04(17) . . ?
F12 C40 C35 113.93(16) . . ?
F13 C40 C35 110.38(17) . . ?
O1 C41 C43 120.6(2) . . ?
O1 C41 C42 121.1(2) . . ?
C43 C41 C42 118.3(3) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
O2 C35 C38 128.84(18) . . ?
O2 C35 C40 113.50(16) . . ?
C38 C35 C40 117.55(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.1(3) . . . . ?
Mn1 N1 C1 C2 174.65(14) . . . . ?
N1 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C1 N1 C5 C4 -0.5(3) . . . . ?
Mn1 N1 C5 C4 -175.10(13) . . . . ?
C1 N1 C5 P1 177.87(13) . . . 2_666 ?
Mn1 N1 C5 P1 3.2(2) . . . 2_666 ?
C3 C4 C5 N1 0.7(3) . . . . ?
C3 C4 C5 P1 -177.68(14) . . . 2_666 ?
N2 C6 C7 C8 -0.3(3) . . . . ?
P1 C6 C7 C8 178.43(15) 2_666 . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C9 C10 N2 -0.5(3) . . . . ?
C9 C10 N2 C6 0.5(3) . . . . ?
C9 C10 N2 Mn1 178.96(14) . . . . ?
C7 C6 N2 C10 -0.2(3) . . . . ?
P1 C6 N2 C10 -178.79(13) 2_666 . . . ?
C7 C6 N2 Mn1 -178.54(13) . . . . ?
P1 C6 N2 Mn1 2.8(2) 2_666 . . . ?
C5 P1 C12 N3 -52.58(16) 2_666 . . . ?
C6 P1 C12 N3 52.64(16) 2_666 . . . ?
C5 P1 C12 C13 125.59(15) 2_666 . . . ?
C6 P1 C12 C13 -129.18(15) 2_666 . . . ?
N3 C12 C13 C14 2.1(3) . . . . ?
P1 C12 C13 C14 -176.05(15) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C16 -1.5(3) . . . . ?
C14 C15 C16 N3 1.3(3) . . . . ?
C15 C16 N3 C12 0.7(3) . . . . ?
C15 C16 N3 Mn1 178.20(15) . . . . ?
C13 C12 N3 C16 -2.4(3) . . . . ?
P1 C12 N3 C16 175.72(14) . . . . ?
C13 C12 N3 Mn1 -179.79(13) . . . . ?
P1 C12 N3 Mn1 -1.7(2) . . . . ?
Mn2 O6 C19 C24 -3.5(3) . . . . ?
Mn2 O6 C19 C20 177.20(13) . . . . ?
O6 C19 C20 F18 48.5(6) . . . . ?
C24 C19 C20 F18 -130.9(6) . . . . ?
O6 C19 C20 F16 171.8(5) . . . . ?
C24 C19 C20 F16 -7.6(5) . . . . ?
O6 C19 C20 F17 -72.9(5) . . . . ?
C24 C19 C20 F17 107.7(5) . . . . ?
O6 C19 C24 C25 0.2(3) . . . . ?
C20 C19 C24 C25 179.51(17) . . . . ?
C19 C24 C25 O7 1.5(3) . . . . ?
C19 C24 C25 C27 -175.73(17) . . . . ?
C24 C25 O7 Mn2 0.4(3) . . . . ?
C27 C25 O7 Mn2 177.68(11) . . . . ?
O7 C25 C27 F1 45.7(2) . . . . ?
C24 C25 C27 F1 -136.61(17) . . . . ?
O7 C25 C27 F14 -72.9(2) . . . . ?
C24 C25 C27 F14 104.78(18) . . . . ?
O7 C25 C27 F15 167.24(16) . . . . ?
C24 C25 C27 F15 -15.1(2) . . . . ?
Mn2 O5 C31 C32 16.8(3) . . . . ?
Mn2 O5 C31 C36 -165.04(16) . . . . ?
O5 C31 C32 C33 2.7(4) . . . . ?
C36 C31 C32 C33 -175.3(2) . . . . ?
C31 C32 C33 O4 -1.0(4) . . . . ?
C31 C32 C33 C34 178.8(2) . . . . ?
O4 C33 C34 F3 61.9(3) . . . . ?
C32 C33 C34 F3 -117.9(3) . . . . ?
O4 C33 C34 F4 -57.3(3) . . . . ?
C32 C33 C34 F4 122.9(3) . . . . ?
O4 C33 C34 F2 -177.1(2) . . . . ?
C32 C33 C34 F2 3.1(3) . . . . ?
C32 C33 O4 Mn2 -20.2(3) . . . . ?
C34 C33 O4 Mn2 160.01(15) . . . . ?
O5 C31 C36 F6 44.3(3) . . . . ?
C32 C31 C36 F6 -137.4(2) . . . . ?
O5 C31 C36 F7 166.2(2) . . . . ?
C32 C31 C36 F7 -15.4(4) . . . . ?
O5 C31 C36 F5 -73.3(3) . . . . ?
C32 C31 C36 F5 105.0(2) . . . . ?
Mn2 O3 C37 C38 -13.9(3) . . . . ?
Mn2 O3 C37 C39 164.07(12) . . . . ?
O3 C37 C38 C35 -1.9(3) . . . . ?
C39 C37 C38 C35 -179.87(18) . . . . ?
O3 C37 C39 F9 -78.2(2) . . . . ?
C38 C37 C39 F9 100.1(2) . . . . ?
O3 C37 C39 F10 40.7(2) . . . . ?
C38 C37 C39 F10 -141.06(18) . . . . ?
O3 C37 C39 F8 160.88(17) . . . . ?
C38 C37 C39 F8 -20.9(3) . . . . ?
Mn2 O2 C35 C38 16.8(3) . . . . ?
Mn2 O2 C35 C40 -167.28(13) . . . . ?
C37 C38 C35 O2 0.4(3) . . . . ?
C37 C38 C35 C40 -175.37(18) . . . . ?
F11 C40 C35 O2 39.4(2) . . . . ?
F12 C40 C35 O2 162.09(18) . . . . ?
F13 C40 C35 O2 -79.0(2) . . . . ?
F11 C40 C35 C38 -144.13(19) . . . . ?
F12 C40 C35 C38 -21.5(3) . . . . ?
F13 C40 C35 C38 97.4(2) . . . . ?

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
C16 H13 F14 0.93(2) 2.59(2) 3.432(2) 151.4(18) 1_455
C16 H13 F1 0.93(2) 2.59(2) 3.371(2) 141.5(17) 1_455
C10 H12 O1 0.93(2) 2.39(2) 3.316(3) 170.1(18) 2_666
C9 H11 O2 0.96(2) 2.37(2) 3.261(2) 153(2) 2_676
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C2 H6 F18 0.97(2) 2.62(2) 3.141(4) 114.3(16) 1_545
C43 H43C O4 0.96 2.58 3.390(4) 142.4 1_545
C16 H13 F14 0.93(2) 2.59(2) 3.432(2) 151.4(18) 1_455
C16 H13 F1 0.93(2) 2.59(2) 3.371(2) 141.5(17) 1_455
C10 H12 O1 0.93(2) 2.39(2) 3.316(3) 170.1(18) 2_666
C9 H11 O2 0.96(2) 2.37(2) 3.261(2) 153(2) 2_676
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C43 H43C O4 0.96 2.58 3.390(4) 142.4 1_545
C16 H13 F14 0.93(2) 2.59(2) 3.432(2) 151.4(18) 1_455
C16 H13 F1 0.93(2) 2.59(2) 3.371(2) 141.5(17) 1_455
C10 H12 O1 0.93(2) 2.39(2) 3.316(3) 170.1(18) 2_666
C9 H11 O2 0.96(2) 2.37(2) 3.261(2) 153(2) 2_676
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C43 H43C O4 0.96 2.58 3.390(4) 142.4 1_545
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C43 H43C O4 0.96 2.58 3.390(4) 142.4 1_545
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C43 H43C O4 0.96 2.58 3.390(4) 142.4 1_545
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C43 H43C O4 0.96 2.58 3.390(4) 142.4 1_545
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C2 H6 F12 0.97(2) 2.81(2) 3.585(2) 138.3(17) 1_445
C2 H6 F18 0.97(2) 2.62(2) 3.141(4) 114.3(16) 1_545
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C43 H43C O4 0.96 2.58 3.390(4) 142.4 1_545
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C43 H43C O4 0.96 2.58 3.390(4) 142.4 1_545
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C43 H43C O4 0.96 2.58 3.390(4) 142.4 1_545
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C43 H43C O4 0.96 2.58 3.390(4) 142.4 1_545
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C43 H43C O4 0.96 2.58 3.390(4) 142.4 1_545
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C9 H11 O2 0.96(2) 2.37(2) 3.261(2) 153(2) 2_676
C10 H12 O1 0.93(2) 2.39(2) 3.316(3) 170.1(18) 2_666
C16 H13 F1 0.93(2) 2.59(2) 3.371(2) 141.5(17) 1_455
C16 H13 F14 0.93(2) 2.59(2) 3.432(2) 151.4(18) 1_455
C43 H43C O4 0.96 2.58 3.390(4) 142.4 1_545
C2 H6 F18 0.97(2) 2.62(2) 3.141(4) 114.3(16) 1_545
C4 H7 O3 0.93(2) 2.52(2) 3.373(2) 153.2(18) 1_455
C9 H11 O2 0.96(2) 2.37(2) 3.261(2) 153(2) 2_676
C10 H12 O1 0.93(2) 2.39(2) 3.316(3) 170.1(18) 2_666
C16 H13 F1 0.93(2) 2.59(2) 3.371(2) 141.5(17) 1_455
C16 H13 F14 0.93(2) 2.59(2) 3.432(2) 151.4(18) 1_455

_refine_diff_density_max         0.584
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.071

_shelxl_version_number           2013-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_mo_Artemev_141014_0m
_database_code_depnum_ccdc_archive 'CCDC 1033904'
_audit_update_record             
;
2014-11-13 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H15 Co F6 N3 O4 P, C5 H F6 O2'
_chemical_formula_sum            'C25 H16 Co F12 N3 O6 P'
_chemical_formula_weight         772.27

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   8.7336(7)
_cell_length_b                   15.7594(12)
_cell_length_c                   11.7574(9)
_cell_angle_alpha                90
_cell_angle_beta                 111.126(3)
_cell_angle_gamma                90
_cell_volume                     1509.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_F_000             770
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.740
_shelx_estimated_absorpt_T_min   0.806
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(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            42752
_diffrn_reflns_av_unetI/netI     0.0943
_diffrn_reflns_av_R_equivalents  0.0987
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.500
_diffrn_reflns_theta_max         30.083
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8842
_reflns_number_gt                6589
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.932
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0304P)²+0.4789P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2565 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.020(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8842
_refine_ls_number_parameters     447
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.0910
_refine_ls_wR_factor_gt          0.0820
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Co1 Co 0.18625(6) 0.16247(3) 0.09096(4) 0.01167(12) Uani 1 1 d . . . . .
P1 P 0.07363(12) 0.34279(6) -0.05675(9) 0.0113(2) Uani 1 1 d . . . . .
O1 O 0.0243(4) 0.42326(18) -0.1250(2) 0.0178(6) Uani 1 1 d . . . . .
O2 O 0.4160(4) 0.10645(18) 0.1473(3) 0.0157(6) Uani 1 1 d . . . . .
F3 F 0.7384(4) 0.0430(2) 0.2564(3) 0.0455(8) Uani 1 1 d . . . . .
F1 F 0.5848(4) -0.0219(2) 0.0960(3) 0.0476(9) Uani 1 1 d . . . . .
F2 F 0.6324(4) -0.0780(2) 0.2698(3) 0.0483(9) Uani 1 1 d . . . . .
F4 F 0.1711(6) -0.0631(2) 0.4032(3) 0.0664(13) Uani 1 1 d . . . . .
F6 F 0.3125(4) 0.0303(2) 0.5222(2) 0.0346(7) Uani 1 1 d . . . . .
F5 F 0.0647(4) 0.0570(3) 0.4170(4) 0.0855(17) Uani 1 1 d . . . . .
F9 F 0.8762(5) -0.1071(2) 0.5109(3) 0.0605(11) Uani 1 1 d . . . . .
F10 F 0.6549(8) 0.1621(4) 0.4920(3) 0.126(2) Uani 1 1 d . . . . .
F7 F 1.1170(5) -0.1135(3) 0.6414(4) 0.0680(12) Uani 1 1 d . . . . .
F8 F 0.9236(5) -0.1810(2) 0.6711(3) 0.0561(10) Uani 1 1 d . . . . .
O6 O 1.0048(4) -0.0391(2) 0.8138(3) 0.0283(8) Uani 1 1 d . . . . .
F14 F 0.5379(5) 0.1717(3) 0.6169(6) 0.108(2) Uani 1 1 d . . . . .
F13 F 0.7397(4) 0.2498(2) 0.6367(4) 0.0620(11) Uani 1 1 d . . . . .
C24 C -0.2428(6) 0.3276(3) -0.0557(4) 0.0242(10) Uani 1 1 d . . . . .
C25 C -0.3611(6) 0.2870(3) -0.0244(5) 0.0315(12) Uani 1 1 d . . . . .
O3 O 0.1773(4) 0.11996(18) 0.2590(2) 0.0160(6) Uani 1 1 d . . . . .
O4 O 0.0838(4) 0.0489(2) 0.0224(3) 0.0220(7) Uani 1 1 d D . . . .
H13 H 0.062(6) 0.015(3) 0.067(3) 0.033 Uiso 1 1 d D U . . .
H12 H 0.024(5) 0.040(3) -0.0477(17) 0.033 Uiso 1 1 d D U . . .
O5 O 0.8418(4) 0.1215(2) 0.8013(3) 0.0330(8) Uani 1 1 d . . . . .
N1 N 0.2960(4) 0.2828(2) 0.1538(3) 0.0136(7) Uani 1 1 d . . . . .
N2 N 0.1993(4) 0.1905(2) -0.0824(3) 0.0129(7) Uani 1 1 d . . . . .
N3 N -0.0465(4) 0.2204(2) 0.0481(3) 0.0143(7) Uani 1 1 d . . . . .
C1 C 0.4198(5) 0.2897(3) 0.2616(4) 0.0183(9) Uani 1 1 d . . . . .
H10 H 0.4576 0.2411 0.3080 0.022 Uiso 1 1 calc R U . . .
C2 C 0.4931(6) 0.3665(3) 0.3062(4) 0.0263(11) Uani 1 1 d . . . . .
H9 H 0.5790 0.3693 0.3812 0.032 Uiso 1 1 calc R U . . .
C3 C 0.4369(6) 0.4395(3) 0.2379(4) 0.0224(10) Uani 1 1 d . . . . .
H8 H 0.4840 0.4919 0.2666 0.027 Uiso 1 1 calc R U . . .
C4 C 0.3097(6) 0.4331(3) 0.1262(4) 0.0192(9) Uani 1 1 d . . . . .
H7 H 0.2698 0.4810 0.0784 0.023 Uiso 1 1 calc R U . . .
C5 C 0.2433(5) 0.3540(2) 0.0875(3) 0.0127(8) Uani 1 1 d . . . . .
C6 C 0.1406(5) 0.2641(3) -0.1410(3) 0.0127(8) Uani 1 1 d . . . . .
C7 C 0.2487(5) 0.1314(3) -0.1430(4) 0.0194(9) Uani 1 1 d . . . . .
H4 H 0.2898 0.0805 -0.1041 0.023 Uiso 1 1 calc R U . . .
C8 C 0.2408(6) 0.1432(3) -0.2621(4) 0.0235(10) Uani 1 1 d . . . . .
H3 H 0.2756 0.1006 -0.3018 0.028 Uiso 1 1 calc R U . . .
C9 C 0.1813(6) 0.2185(3) -0.3209(4) 0.0212(10) Uani 1 1 d . . . . .
H1 H 0.1757 0.2274 -0.4004 0.025 Uiso 1 1 calc R U . . .
C10 C 0.1296(5) 0.2808(3) -0.2594(3) 0.0148(8) Uani 1 1 d . . . . .
H2 H 0.0888 0.3323 -0.2966 0.018 Uiso 1 1 calc R U . . .
C11 C -0.0886(5) 0.2924(3) -0.0184(3) 0.0140(8) Uani 1 1 d . . . . .
C12 C -0.3213(6) 0.2142(3) 0.0447(4) 0.0273(11) Uani 1 1 d . . . . .
H6 H -0.3995 0.1865 0.0679 0.033 Uiso 1 1 calc R U . . .
C13 C -0.1629(5) 0.1827(3) 0.0792(4) 0.0206(10) Uani 1 1 d . . . . .
H5 H -0.1365 0.1334 0.1257 0.025 Uiso 1 1 calc R U . . .
C14 C 0.2513(5) 0.0560(3) 0.3134(4) 0.0164(9) Uani 1 1 d . . . . .
C15 C 0.3831(5) 0.0132(3) 0.2963(4) 0.0189(9) Uani 1 1 d . . . . .
H11 H 0.4228 -0.0364 0.3398 0.023 Uiso 1 1 calc R U . . .
C16 C 0.4545(5) 0.0426(3) 0.2175(4) 0.0150(9) Uani 1 1 d . . . . .
C17 C 0.6052(6) -0.0037(3) 0.2114(4) 0.0242(10) Uani 1 1 d . . . . .
C18 C 0.1951(6) 0.0213(3) 0.4136(4) 0.0240(10) Uani 1 1 d . . . . .
C19 C 0.9600(7) -0.1090(4) 0.6300(5) 0.0331(12) Uani 1 1 d . . . . .
C20 C 0.9318(6) -0.0327(3) 0.7010(4) 0.0242(10) Uani 1 1 d . . . . .
C21 C 0.8338(6) 0.0328(3) 0.6347(4) 0.0272(11) Uani 1 1 d . . . . .
H14 H 0.7906 0.0290 0.5501 0.033 Uiso 1 1 calc R U . . .
C22 C 0.7973(6) 0.1049(3) 0.6914(4) 0.0281(11) Uani 1 1 d . . . . .
C23 C 0.6845(7) 0.1727(4) 0.6087(5) 0.0399(14) Uani 1 1 d . . . . .
H15 H -0.461(7) 0.312(3) -0.050(5) 0.037(15) Uiso 1 1 d . . . . .
H16 H -0.268(5) 0.375(3) -0.101(4) 0.004(10) 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
Co1 O4 2.033(3) . ?
Co1 O2 2.070(3) . ?
Co1 O3 2.114(3) . ?
Co1 N3 2.116(3) . ?
Co1 N2 2.128(3) . ?
Co1 N1 2.133(3) . ?
P1 O1 1.479(3) . ?
P1 C6 1.810(4) . ?
P1 C5 1.815(4) . ?
P1 C11 1.817(4) . ?
O2 C16 1.267(5) . ?
F3 C17 1.316(6) . ?
F1 C17 1.334(5) . ?
F2 C17 1.335(5) . ?
F4 C18 1.345(6) . ?
F6 C18 1.326(5) . ?
F5 C18 1.284(6) . ?
F9 C19 1.326(6) . ?
F10 C23 1.312(6) . ?
F7 C19 1.331(6) . ?
F8 C19 1.316(6) . ?
O6 C20 1.251(5) . ?
F14 C23 1.318(7) . ?
F13 C23 1.306(7) . ?
C24 C25 1.374(7) . ?
C24 C11 1.374(6) . ?
C24 H16 0.90(4) . ?
C25 C12 1.376(7) . ?
C25 H15 0.90(6) . ?
O3 C14 1.243(5) . ?
O4 H13 0.818(14) . ?
O4 H12 0.813(14) . ?
O5 C22 1.236(6) . ?
N1 C1 1.342(5) . ?
N1 C5 1.349(5) . ?
N2 C7 1.335(5) . ?
N2 C6 1.353(5) . ?
N3 C13 1.337(5) . ?
N3 C11 1.351(5) . ?
C1 C2 1.381(6) . ?
C1 H10 0.9300 . ?
C2 C3 1.388(6) . ?
C2 H9 0.9300 . ?
C3 C4 1.385(6) . ?
C3 H8 0.9300 . ?
C4 C5 1.382(6) . ?
C4 H7 0.9300 . ?
C6 C10 1.386(5) . ?
C7 C8 1.389(6) . ?
C7 H4 0.9300 . ?
C8 C9 1.376(6) . ?
C8 H3 0.9300 . ?
C9 C10 1.388(6) . ?
C9 H1 0.9300 . ?
C10 H2 0.9300 . ?
C12 C13 1.386(6) . ?
C12 H6 0.9300 . ?
C13 H5 0.9300 . ?
C14 C15 1.410(6) . ?
C14 C18 1.531(6) . ?
C15 C16 1.371(6) . ?
C15 H11 0.9300 . ?
C16 C17 1.528(6) . ?
C19 C20 1.535(7) . ?
C20 C21 1.387(7) . ?
C21 C22 1.410(7) . ?
C21 H14 0.9300 . ?
C22 C23 1.538(8) . ?

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
O4 Co1 O2 89.34(13) . . ?
O4 Co1 O3 86.12(12) . . ?
O2 Co1 O3 85.64(11) . . ?
O4 Co1 N3 92.16(14) . . ?
O2 Co1 N3 175.47(13) . . ?
O3 Co1 N3 90.20(12) . . ?
O4 Co1 N2 88.32(12) . . ?
O2 Co1 N2 90.82(12) . . ?
O3 Co1 N2 173.44(12) . . ?
N3 Co1 N2 93.50(13) . . ?
O4 Co1 N1 176.86(13) . . ?
O2 Co1 N1 90.32(12) . . ?
O3 Co1 N1 96.97(12) . . ?
N3 Co1 N1 88.41(13) . . ?
N2 Co1 N1 88.56(12) . . ?
O1 P1 C6 112.24(18) . . ?
O1 P1 C5 113.83(18) . . ?
C6 P1 C5 105.18(18) . . ?
O1 P1 C11 114.14(19) . . ?
C6 P1 C11 105.71(19) . . ?
C5 P1 C11 104.92(18) . . ?
C16 O2 Co1 123.1(3) . . ?
C25 C24 C11 118.1(4) . . ?
C25 C24 H16 120(3) . . ?
C11 C24 H16 122(3) . . ?
C24 C25 C12 119.5(5) . . ?
C24 C25 H15 116(3) . . ?
C12 C25 H15 124(3) . . ?
C14 O3 Co1 123.4(3) . . ?
Co1 O4 H13 120(3) . . ?
Co1 O4 H12 126(3) . . ?
H13 O4 H12 109(3) . . ?
C1 N1 C5 117.9(3) . . ?
C1 N1 Co1 120.6(3) . . ?
C5 N1 Co1 121.5(3) . . ?
C7 N2 C6 117.6(3) . . ?
C7 N2 Co1 120.4(3) . . ?
C6 N2 Co1 121.6(3) . . ?
C13 N3 C11 117.1(4) . . ?
C13 N3 Co1 120.2(3) . . ?
C11 N3 Co1 122.5(3) . . ?
N1 C1 C2 122.4(4) . . ?
N1 C1 H10 118.8 . . ?
C2 C1 H10 118.8 . . ?
C1 C2 C3 119.2(4) . . ?
C1 C2 H9 120.4 . . ?
C3 C2 H9 120.4 . . ?
C4 C3 C2 118.9(4) . . ?
C4 C3 H8 120.5 . . ?
C2 C3 H8 120.5 . . ?
C5 C4 C3 118.4(4) . . ?
C5 C4 H7 120.8 . . ?
C3 C4 H7 120.8 . . ?
N1 C5 C4 123.1(4) . . ?
N1 C5 P1 116.9(3) . . ?
C4 C5 P1 120.0(3) . . ?
N2 C6 C10 123.4(4) . . ?
N2 C6 P1 116.6(3) . . ?
C10 C6 P1 120.0(3) . . ?
N2 C7 C8 122.4(4) . . ?
N2 C7 H4 118.8 . . ?
C8 C7 H4 118.8 . . ?
C9 C8 C7 119.6(4) . . ?
C9 C8 H3 120.2 . . ?
C7 C8 H3 120.2 . . ?
C8 C9 C10 118.9(4) . . ?
C8 C9 H1 120.5 . . ?
C10 C9 H1 120.5 . . ?
C6 C10 C9 118.1(4) . . ?
C6 C10 H2 120.9 . . ?
C9 C10 H2 120.9 . . ?
N3 C11 C24 123.7(4) . . ?
N3 C11 P1 115.9(3) . . ?
C24 C11 P1 120.4(3) . . ?
C25 C12 C13 118.9(4) . . ?
C25 C12 H6 120.5 . . ?
C13 C12 H6 120.5 . . ?
N3 C13 C12 122.6(4) . . ?
N3 C13 H5 118.7 . . ?
C12 C13 H5 118.7 . . ?
O3 C14 C15 127.9(4) . . ?
O3 C14 C18 115.8(4) . . ?
C15 C14 C18 116.3(4) . . ?
C16 C15 C14 121.9(4) . . ?
C16 C15 H11 119.0 . . ?
C14 C15 H11 119.0 . . ?
O2 C16 C15 129.1(4) . . ?
O2 C16 C17 112.3(4) . . ?
C15 C16 C17 118.6(4) . . ?
F3 C17 F1 107.7(4) . . ?
F3 C17 F2 108.4(4) . . ?
F1 C17 F2 105.5(4) . . ?
F3 C17 C16 111.4(4) . . ?
F1 C17 C16 110.4(4) . . ?
F2 C17 C16 113.1(4) . . ?
F5 C18 F6 108.0(4) . . ?
F5 C18 F4 109.0(5) . . ?
F6 C18 F4 103.5(4) . . ?
F5 C18 C14 113.7(4) . . ?
F6 C18 C14 110.6(4) . . ?
F4 C18 C14 111.5(4) . . ?
F8 C19 F9 107.1(5) . . ?
F8 C19 F7 107.1(5) . . ?
F9 C19 F7 105.3(4) . . ?
F8 C19 C20 111.7(4) . . ?
F9 C19 C20 114.9(4) . . ?
F7 C19 C20 110.4(4) . . ?
O6 C20 C21 129.2(5) . . ?
O6 C20 C19 113.1(4) . . ?
C21 C20 C19 117.7(4) . . ?
C20 C21 C22 122.2(4) . . ?
C20 C21 H14 118.9 . . ?
C22 C21 H14 118.9 . . ?
O5 C22 C21 128.7(5) . . ?
O5 C22 C23 113.7(5) . . ?
C21 C22 C23 117.6(4) . . ?
F13 C23 F10 107.3(6) . . ?
F13 C23 F14 105.8(5) . . ?
F10 C23 F14 104.2(5) . . ?
F13 C23 C22 113.1(4) . . ?
F10 C23 C22 114.4(5) . . ?
F14 C23 C22 111.4(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
C11 C24 C25 C12 1.4(8) . . . . ?
C5 N1 C1 C2 0.3(6) . . . . ?
Co1 N1 C1 C2 -179.3(4) . . . . ?
N1 C1 C2 C3 0.3(7) . . . . ?
C1 C2 C3 C4 -0.5(7) . . . . ?
C2 C3 C4 C5 0.2(7) . . . . ?
C1 N1 C5 C4 -0.7(6) . . . . ?
Co1 N1 C5 C4 178.9(3) . . . . ?
C1 N1 C5 P1 -179.1(3) . . . . ?
Co1 N1 C5 P1 0.6(4) . . . . ?
C3 C4 C5 N1 0.4(6) . . . . ?
C3 C4 C5 P1 178.8(3) . . . . ?
O1 P1 C5 N1 -179.2(3) . . . . ?
C6 P1 C5 N1 -55.9(3) . . . . ?
C11 P1 C5 N1 55.4(3) . . . . ?
O1 P1 C5 C4 2.4(4) . . . . ?
C6 P1 C5 C4 125.7(3) . . . . ?
C11 P1 C5 C4 -123.1(3) . . . . ?
C7 N2 C6 C10 0.0(6) . . . . ?
Co1 N2 C6 C10 -172.4(3) . . . . ?
C7 N2 C6 P1 179.7(3) . . . . ?
Co1 N2 C6 P1 7.3(4) . . . . ?
O1 P1 C6 N2 175.4(3) . . . . ?
C5 P1 C6 N2 51.1(3) . . . . ?
C11 P1 C6 N2 -59.6(3) . . . . ?
O1 P1 C6 C10 -4.9(4) . . . . ?
C5 P1 C6 C10 -129.1(3) . . . . ?
C11 P1 C6 C10 120.2(3) . . . . ?
C6 N2 C7 C8 -0.3(6) . . . . ?
Co1 N2 C7 C8 172.2(3) . . . . ?
N2 C7 C8 C9 0.4(7) . . . . ?
C7 C8 C9 C10 -0.3(7) . . . . ?
N2 C6 C10 C9 0.2(6) . . . . ?
P1 C6 C10 C9 -179.5(3) . . . . ?
C8 C9 C10 C6 0.0(6) . . . . ?
C13 N3 C11 C24 -0.5(6) . . . . ?
Co1 N3 C11 C24 174.7(3) . . . . ?
C13 N3 C11 P1 179.0(3) . . . . ?
Co1 N3 C11 P1 -5.8(4) . . . . ?
C25 C24 C11 N3 -0.5(7) . . . . ?
C25 C24 C11 P1 180.0(4) . . . . ?
O1 P1 C11 N3 -177.5(3) . . . . ?
C6 P1 C11 N3 58.6(3) . . . . ?
C5 P1 C11 N3 -52.3(3) . . . . ?
O1 P1 C11 C24 2.0(4) . . . . ?
C6 P1 C11 C24 -121.8(4) . . . . ?
C5 P1 C11 C24 127.3(4) . . . . ?
C24 C25 C12 C13 -1.2(8) . . . . ?
C11 N3 C13 C12 0.7(6) . . . . ?
Co1 N3 C13 C12 -174.6(3) . . . . ?
C25 C12 C13 N3 0.1(7) . . . . ?
Co1 O3 C14 C15 17.8(6) . . . . ?
Co1 O3 C14 C18 -164.0(3) . . . . ?
O3 C14 C15 C16 4.2(7) . . . . ?
C18 C14 C15 C16 -173.9(4) . . . . ?
Co1 O2 C16 C15 -20.8(6) . . . . ?
Co1 O2 C16 C17 161.0(3) . . . . ?
C14 C15 C16 O2 -2.7(7) . . . . ?
C14 C15 C16 C17 175.3(4) . . . . ?
O2 C16 C17 F3 67.3(5) . . . . ?
C15 C16 C17 F3 -111.1(5) . . . . ?
O2 C16 C17 F1 -52.3(5) . . . . ?
C15 C16 C17 F1 129.3(4) . . . . ?
O2 C16 C17 F2 -170.2(4) . . . . ?
C15 C16 C17 F2 11.4(6) . . . . ?
O3 C14 C18 F5 8.3(6) . . . . ?
C15 C14 C18 F5 -173.3(5) . . . . ?
O3 C14 C18 F6 -113.4(4) . . . . ?
C15 C14 C18 F6 65.0(5) . . . . ?
O3 C14 C18 F4 132.0(4) . . . . ?
C15 C14 C18 F4 -49.6(5) . . . . ?
F8 C19 C20 O6 53.7(6) . . . . ?
F9 C19 C20 O6 175.9(4) . . . . ?
F7 C19 C20 O6 -65.3(6) . . . . ?
F8 C19 C20 C21 -126.9(5) . . . . ?
F9 C19 C20 C21 -4.8(7) . . . . ?
F7 C19 C20 C21 114.1(5) . . . . ?
O6 C20 C21 C22 -2.1(8) . . . . ?
C19 C20 C21 C22 178.6(4) . . . . ?
C20 C21 C22 O5 -0.3(9) . . . . ?
C20 C21 C22 C23 -178.8(5) . . . . ?
O5 C22 C23 F13 47.7(7) . . . . ?
C21 C22 C23 F13 -133.5(5) . . . . ?
O5 C22 C23 F10 170.9(6) . . . . ?
C21 C22 C23 F10 -10.3(8) . . . . ?
O5 C22 C23 F14 -71.4(6) . . . . ?
C21 C22 C23 F14 107.4(6) . . . . ?

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
C13 H5 O3 0.93 2.63 3.122(5) 113.7 .
C13 H5 F3 0.93 2.61 3.350(6) 137.4 1_455
C12 H6 O2 0.93 2.48 3.405(6) 174.1 1_455
C8 H3 F6 0.93 2.47 3.338(5) 155.6 1_554
C1 H10 F10 0.93 2.55 3.405(6) 152.6 .
O4 H12 O5 0.813(14) 2.30(4) 2.928(5) 135(5) 1_454
O4 H12 O6 0.813(14) 2.01(4) 2.683(4) 139(5) 1_454
O4 H13 O1 0.818(14) 1.87(2) 2.663(4) 164(4) 2_545
C13 H5 F3 0.93 2.61 3.350(6) 137.4 1_455
C13 H5 O3 0.93 2.63 3.122(5) 113.7 .
O4 H12 O5 0.813(14) 2.30(4) 2.928(5) 135(5) 1_454
C1 H10 F10 0.93 2.55 3.405(6) 152.6 .
C13 H5 F3 0.93 2.61 3.350(6) 137.4 1_455
C13 H5 O3 0.93 2.63 3.122(5) 113.7 .
O4 H13 O1 0.818(14) 1.87(2) 2.663(4) 164(4) 2_545
O4 H12 O5 0.813(14) 2.30(4) 2.928(5) 135(5) 1_454
C1 H10 F10 0.93 2.55 3.405(6) 152.6 .
C12 H6 O2 0.93 2.48 3.405(6) 174.1 1_455
C13 H5 F3 0.93 2.61 3.350(6) 137.4 1_455
C13 H5 O3 0.93 2.63 3.122(5) 113.7 .
O4 H13 O1 0.818(14) 1.87(2) 2.663(4) 164(4) 2_545
O4 H12 O6 0.813(14) 2.01(4) 2.683(4) 139(5) 1_454
O4 H12 O5 0.813(14) 2.30(4) 2.928(5) 135(5) 1_454
C1 H10 F10 0.93 2.55 3.405(6) 152.6 .
C8 H3 F6 0.93 2.47 3.338(5) 155.6 1_554
C12 H6 O2 0.93 2.48 3.405(6) 174.1 1_455
C13 H5 F3 0.93 2.61 3.350(6) 137.4 1_455
C13 H5 O3 0.93 2.63 3.122(5) 113.7 .
O4 H13 O1 0.818(14) 1.87(2) 2.663(4) 164(4) 2_545
O4 H12 O6 0.813(14) 2.01(4) 2.683(4) 139(5) 1_454
O4 H12 O5 0.813(14) 2.30(4) 2.928(5) 135(5) 1_454
C1 H10 F10 0.93 2.55 3.405(6) 152.6 .
C8 H3 F6 0.93 2.47 3.338(5) 155.6 1_554
C12 H6 O2 0.93 2.48 3.405(6) 174.1 1_455
C13 H5 F3 0.93 2.61 3.350(6) 137.4 1_455
C13 H5 O3 0.93 2.63 3.122(5) 113.7 .

_refine_diff_density_max         0.818
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.085

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_mo_Artemev_021214_0m
_database_code_depnum_ccdc_archive 'CCDC 1431160'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          435
_chemical_formula_moiety         'C30 H24 Cu N6 P2, 2(C5 H F6 O2)'
_chemical_formula_sum            'C40 H26 Cu F12 N6 O4 P2'
_chemical_formula_weight         1008.16

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

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

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

_cell_length_a                   11.3926(4)
_cell_length_b                   12.4104(4)
_cell_length_c                   14.1878(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.9020(10)
_cell_angle_gamma                90
_cell_volume                     1995.33(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prizm
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_F_000             1014
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.736
_shelx_estimated_absorpt_T_min   0.573
_shelx_estimated_absorpt_T_max   0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5730
_exptl_absorpt_correction_T_max  0.8340
_exptl_absorpt_process_details   ?
_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  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            67156
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.185
_diffrn_reflns_theta_max         30.079
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5842
_reflns_number_gt                4821
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0487P)²+1.8812P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5842
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.0000 0.0000 0.01304(8) Uani 1 2 d S . P . .
P1 P 0.79357(4) -0.06056(4) 0.03671(3) 0.01662(10) Uani 1 1 d . . . . .
F1 F 0.30394(16) 0.26319(13) 0.76963(15) 0.0634(5) Uani 1 1 d . . . . .
F2 F 0.06305(15) 0.74849(13) 0.89578(11) 0.0498(4) Uani 1 1 d . . . . .
F3 F -0.03991(11) 0.60402(14) 0.89794(12) 0.0505(4) Uani 1 1 d . . . . .
F4 F 0.05222(11) 0.66437(11) 1.02600(9) 0.0339(3) Uani 1 1 d . . . . .
F5 F 0.17330(19) 0.35548(12) 0.68285(10) 0.0571(5) Uani 1 1 d . . . . .
F6 F 0.12875(13) 0.27564(11) 0.80710(9) 0.0386(3) Uani 1 1 d . . . . .
O1 O 0.26550(12) 0.63118(13) 0.95085(12) 0.0334(4) Uani 1 1 d . . . . .
O2 O 0.35742(13) 0.45662(12) 0.83611(11) 0.0294(3) Uani 1 1 d . . . . .
N1 N 0.64554(14) 0.06693(13) -0.08323(11) 0.0216(3) Uani 1 1 d . . . . .
N2 N 0.60966(14) 0.02029(12) 0.13021(12) 0.0195(3) Uani 1 1 d . . . . .
N3 N 0.43134(12) 0.14868(11) 0.01256(10) 0.0145(3) Uani 1 1 d . . . . .
C1 C 0.6254(2) 0.13432(16) -0.15777(14) 0.0286(4) Uani 1 1 d . . . . .
H12 H 0.5478 0.1528 -0.1781 0.034 Uiso 1 1 calc R U . . .
C2 C 0.7146(2) 0.17726(16) -0.20556(15) 0.0328(5) Uani 1 1 d . . . . .
H11 H 0.6966 0.2204 -0.2587 0.039 Uiso 1 1 calc R U . . .
C3 C 0.8297(2) 0.15540(17) -0.17351(15) 0.0310(5) Uani 1 1 d . . . . .
H10 H 0.8912 0.1860 -0.2026 0.037 Uiso 1 1 calc R U . . .
C4 C 0.85253(18) 0.08663(16) -0.09673(14) 0.0251(4) Uani 1 1 d . . . . .
H9 H 0.9298 0.0707 -0.0732 0.030 Uiso 1 1 calc R U . . .
C5 C 0.75847(16) 0.04178(14) -0.05533(12) 0.0183(3) Uani 1 1 d . . . . .
C6 C 0.72573(16) -0.00367(14) 0.13777(13) 0.0177(3) Uani 1 1 d . . . . .
C7 C 0.56337(18) 0.05634(15) 0.20787(14) 0.0244(4) Uani 1 1 d . . . . .
H4 H 0.4833 0.0727 0.2032 0.029 Uiso 1 1 calc R U . . .
C8 C 0.6290(2) 0.07005(16) 0.29377(14) 0.0276(4) Uani 1 1 d . . . . .
H3 H 0.5935 0.0937 0.3462 0.033 Uiso 1 1 calc R U . . .
C9 C 0.7487(2) 0.04831(17) 0.30137(14) 0.0281(4) Uani 1 1 d . . . . .
H2 H 0.7953 0.0587 0.3584 0.034 Uiso 1 1 calc R U . . .
C10 C 0.79780(18) 0.01046(15) 0.22181(14) 0.0229(4) Uani 1 1 d . . . . .
H1 H 0.8779 -0.0052 0.2250 0.027 Uiso 1 1 calc R U . . .
C11 C 0.31379(14) 0.16739(14) 0.00020(12) 0.0155(3) Uani 1 1 d . . . . .
C12 C 0.50421(15) 0.23184(14) 0.03670(12) 0.0170(3) Uani 1 1 d . . . . .
H5 H 0.5850 0.2190 0.0449 0.020 Uiso 1 1 calc R U . . .
C13 C 0.46430(16) 0.33609(14) 0.04999(13) 0.0192(3) Uani 1 1 d . . . . .
H8 H 0.5170 0.3917 0.0669 0.023 Uiso 1 1 calc R U . . .
C14 C 0.34427(17) 0.35478(15) 0.03736(13) 0.0212(4) Uani 1 1 d . . . . .
H6 H 0.3147 0.4236 0.0454 0.025 Uiso 1 1 calc R U . . .
C15 C 0.26811(15) 0.26961(15) 0.01256(13) 0.0189(3) Uani 1 1 d . . . . .
H7 H 0.1870 0.2810 0.0043 0.023 Uiso 1 1 calc R U . . .
C16 C 0.2150(2) 0.33165(17) 0.77269(15) 0.0316(5) Uani 1 1 d . . . . .
C17 C 0.25186(17) 0.43469(15) 0.82980(13) 0.0227(4) Uani 1 1 d . . . . .
C18 C 0.15785(16) 0.49190(15) 0.86371(13) 0.0207(4) Uani 1 1 d . . . . .
H13 H 0.0817 0.4650 0.8507 0.025 Uiso 1 1 calc R U . . .
C19 C 0.17383(16) 0.58727(16) 0.91599(13) 0.0207(3) Uani 1 1 d . . . . .
C20 C 0.06108(17) 0.64990(17) 0.93360(14) 0.0254(4) 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 N3 2.0192(14) . ?
Cu1 N3 2.0192(14) 3_655 ?
Cu1 N2 2.1360(17) . ?
Cu1 N2 2.1361(17) 3_655 ?
Cu1 N1 2.2883(17) 3_655 ?
Cu1 N1 2.2883(17) . ?
P1 C5 1.8359(19) . ?
P1 C6 1.8383(18) . ?
P1 C11 1.8430(17) 3_655 ?
F1 C16 1.327(3) . ?
F2 C20 1.337(3) . ?
F3 C20 1.336(2) . ?
F4 C20 1.337(2) . ?
F5 C16 1.347(3) . ?
F6 C16 1.336(3) . ?
O1 C19 1.235(2) . ?
O2 C17 1.227(2) . ?
N1 C5 1.343(2) . ?
N1 C1 1.349(3) . ?
N2 C7 1.346(2) . ?
N2 C6 1.349(2) . ?
N3 C12 1.347(2) . ?
N3 C11 1.353(2) . ?
C1 C2 1.385(3) . ?
C1 H12 0.9300 . ?
C2 C3 1.371(3) . ?
C2 H11 0.9300 . ?
C3 C4 1.387(3) . ?
C3 H10 0.9300 . ?
C4 C5 1.390(3) . ?
C4 H9 0.9300 . ?
C6 C10 1.388(3) . ?
C7 C8 1.373(3) . ?
C7 H4 0.9300 . ?
C8 C9 1.383(3) . ?
C8 H3 0.9300 . ?
C9 C10 1.392(3) . ?
C9 H2 0.9300 . ?
C10 H1 0.9300 . ?
C11 C15 1.389(2) . ?
C11 P1 1.8429(17) 3_655 ?
C12 C13 1.391(2) . ?
C12 H5 0.9300 . ?
C13 C14 1.380(2) . ?
C13 H8 0.9300 . ?
C14 C15 1.390(3) . ?
C14 H6 0.9300 . ?
C15 H7 0.9300 . ?
C16 C17 1.549(3) . ?
C17 C18 1.410(3) . ?
C18 C19 1.399(3) . ?
C18 H13 0.9300 . ?
C19 C20 1.544(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Cu1 N3 180.0 . 3_655 ?
N3 Cu1 N2 90.77(6) . . ?
N3 Cu1 N2 89.23(6) 3_655 . ?
N3 Cu1 N2 89.23(6) . 3_655 ?
N3 Cu1 N2 90.77(6) 3_655 3_655 ?
N2 Cu1 N2 180.00(5) . 3_655 ?
N3 Cu1 N1 88.76(6) . 3_655 ?
N3 Cu1 N1 91.24(6) 3_655 3_655 ?
N2 Cu1 N1 89.25(6) . 3_655 ?
N2 Cu1 N1 90.75(6) 3_655 3_655 ?
N3 Cu1 N1 91.24(6) . . ?
N3 Cu1 N1 88.76(6) 3_655 . ?
N2 Cu1 N1 90.75(6) . . ?
N2 Cu1 N1 89.25(6) 3_655 . ?
N1 Cu1 N1 180.00(5) 3_655 . ?
C5 P1 C6 102.17(8) . . ?
C5 P1 C11 101.89(8) . 3_655 ?
C6 P1 C11 100.25(8) . 3_655 ?
C5 N1 C1 117.10(18) . . ?
C5 N1 Cu1 119.10(12) . . ?
C1 N1 Cu1 123.76(14) . . ?
C7 N2 C6 118.14(17) . . ?
C7 N2 Cu1 120.24(13) . . ?
C6 N2 Cu1 121.61(12) . . ?
C12 N3 C11 118.53(15) . . ?
C12 N3 Cu1 119.24(11) . . ?
C11 N3 Cu1 122.19(11) . . ?
N1 C1 C2 123.2(2) . . ?
N1 C1 H12 118.4 . . ?
C2 C1 H12 118.4 . . ?
C3 C2 C1 119.12(19) . . ?
C3 C2 H11 120.4 . . ?
C1 C2 H11 120.4 . . ?
C2 C3 C4 118.5(2) . . ?
C2 C3 H10 120.7 . . ?
C4 C3 H10 120.7 . . ?
C3 C4 C5 119.2(2) . . ?
C3 C4 H9 120.4 . . ?
C5 C4 H9 120.4 . . ?
N1 C5 C4 122.61(18) . . ?
N1 C5 P1 120.15(14) . . ?
C4 C5 P1 117.17(14) . . ?
N2 C6 C10 121.94(17) . . ?
N2 C6 P1 120.67(14) . . ?
C10 C6 P1 117.37(14) . . ?
N2 C7 C8 122.95(19) . . ?
N2 C7 H4 118.5 . . ?
C8 C7 H4 118.5 . . ?
C7 C8 C9 119.19(18) . . ?
C7 C8 H3 120.4 . . ?
C9 C8 H3 120.4 . . ?
C8 C9 C10 118.55(19) . . ?
C8 C9 H2 120.7 . . ?
C10 C9 H2 120.7 . . ?
C6 C10 C9 119.19(19) . . ?
C6 C10 H1 120.4 . . ?
C9 C10 H1 120.4 . . ?
N3 C11 C15 121.27(16) . . ?
N3 C11 P1 122.18(13) . 3_655 ?
C15 C11 P1 116.53(13) . 3_655 ?
N3 C12 C13 123.09(16) . . ?
N3 C12 H5 118.5 . . ?
C13 C12 H5 118.5 . . ?
C14 C13 C12 118.17(16) . . ?
C14 C13 H8 120.9 . . ?
C12 C13 H8 120.9 . . ?
C13 C14 C15 119.31(16) . . ?
C13 C14 H6 120.3 . . ?
C15 C14 H6 120.3 . . ?
C11 C15 C14 119.63(16) . . ?
C11 C15 H7 120.2 . . ?
C14 C15 H7 120.2 . . ?
F1 C16 F6 105.76(18) . . ?
F1 C16 F5 107.81(19) . . ?
F6 C16 F5 105.0(2) . . ?
F1 C16 C17 112.3(2) . . ?
F6 C16 C17 114.11(16) . . ?
F5 C16 C17 111.36(17) . . ?
O2 C17 C18 129.52(19) . . ?
O2 C17 C16 115.62(18) . . ?
C18 C17 C16 114.80(18) . . ?
C19 C18 C17 123.02(17) . . ?
C19 C18 H13 118.5 . . ?
C17 C18 H13 118.5 . . ?
O1 C19 C18 130.10(18) . . ?
O1 C19 C20 113.35(17) . . ?
C18 C19 C20 116.55(16) . . ?
F3 C20 F2 106.70(18) . . ?
F3 C20 F4 106.24(17) . . ?
F2 C20 F4 106.05(17) . . ?
F3 C20 C19 115.00(17) . . ?
F2 C20 C19 110.32(17) . . ?
F4 C20 C19 111.98(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.2(3) . . . . ?
Cu1 N1 C1 C2 177.70(15) . . . . ?
N1 C1 C2 C3 -3.4(3) . . . . ?
C1 C2 C3 C4 3.0(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C1 N1 C5 C4 3.5(3) . . . . ?
Cu1 N1 C5 C4 -174.16(14) . . . . ?
C1 N1 C5 P1 -173.27(14) . . . . ?
Cu1 N1 C5 P1 9.07(19) . . . . ?
C3 C4 C5 N1 -3.8(3) . . . . ?
C3 C4 C5 P1 173.03(15) . . . . ?
C6 P1 C5 N1 -59.26(16) . . . . ?
C11 P1 C5 N1 44.12(16) 3_655 . . . ?
C6 P1 C5 C4 123.79(15) . . . . ?
C11 P1 C5 C4 -132.83(14) 3_655 . . . ?
C7 N2 C6 C10 -1.7(3) . . . . ?
Cu1 N2 C6 C10 179.24(13) . . . . ?
C7 N2 C6 P1 176.52(13) . . . . ?
Cu1 N2 C6 P1 -2.6(2) . . . . ?
C5 P1 C6 N2 57.11(16) . . . . ?
C11 P1 C6 N2 -47.55(15) 3_655 . . . ?
C5 P1 C6 C10 -124.62(15) . . . . ?
C11 P1 C6 C10 130.72(14) 3_655 . . . ?
C6 N2 C7 C8 0.3(3) . . . . ?
Cu1 N2 C7 C8 179.36(14) . . . . ?
N2 C7 C8 C9 1.4(3) . . . . ?
C7 C8 C9 C10 -1.6(3) . . . . ?
N2 C6 C10 C9 1.4(3) . . . . ?
P1 C6 C10 C9 -176.85(14) . . . . ?
C8 C9 C10 C6 0.3(3) . . . . ?
C12 N3 C11 C15 -0.4(2) . . . . ?
Cu1 N3 C11 C15 177.62(13) . . . . ?
C12 N3 C11 P1 177.92(13) . . . 3_655 ?
Cu1 N3 C11 P1 -4.01(19) . . . 3_655 ?
C11 N3 C12 C13 0.3(3) . . . . ?
Cu1 N3 C12 C13 -177.80(13) . . . . ?
N3 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
N3 C11 C15 C14 0.5(3) . . . . ?
P1 C11 C15 C14 -177.93(14) 3_655 . . . ?
C13 C14 C15 C11 -0.5(3) . . . . ?
F1 C16 C17 O2 23.4(3) . . . . ?
F6 C16 C17 O2 143.76(19) . . . . ?
F5 C16 C17 O2 -97.6(2) . . . . ?
F1 C16 C17 C18 -158.99(18) . . . . ?
F6 C16 C17 C18 -38.7(3) . . . . ?
F5 C16 C17 C18 80.0(2) . . . . ?
O2 C17 C18 C19 -2.3(3) . . . . ?
C16 C17 C18 C19 -179.46(17) . . . . ?
C17 C18 C19 O1 -9.3(3) . . . . ?
C17 C18 C19 C20 170.18(18) . . . . ?
O1 C19 C20 F3 -179.16(19) . . . . ?
C18 C19 C20 F3 1.2(3) . . . . ?
O1 C19 C20 F2 60.1(2) . . . . ?
C18 C19 C20 F2 -119.49(19) . . . . ?
O1 C19 C20 F4 -57.8(2) . . . . ?
C18 C19 C20 F4 122.64(19) . . . . ?

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
C13 H8 O1 0.93 2.53 3.106(2) 120.2 3_666
C12 H5 O1 0.93 2.52 3.116(2) 122.3 3_666
C7 H4 O2 0.93 2.51 3.118(2) 123.1 4_565
C13 H8 O1 0.93 2.53 3.106(2) 120.2 3_666
C12 H5 O1 0.93 2.52 3.116(2) 122.3 3_666
C7 H4 O2 0.93 2.51 3.118(2) 123.1 4_565
C7 H4 O2 0.93 2.51 3.118(2) 123.1 4_565
C12 H5 O1 0.93 2.52 3.116(2) 122.3 3_666
C13 H8 O1 0.93 2.53 3.106(2) 120.2 3_666
C13 H8 O2 0.93 2.66 3.561(2) 163.2 3_666
C7 H4 O2 0.93 2.51 3.118(2) 123.1 4_565
C12 H5 O1 0.93 2.52 3.116(2) 122.3 3_666
C13 H8 O1 0.93 2.53 3.106(2) 120.2 3_666

_refine_diff_density_max         1.283
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.080

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_mo_Artemev_Cu1_0m
_audit_block_doi                 10.5517/cc1k17d7
_database_code_depnum_ccdc_archive 'CCDC 1431158'
_audit_update_record             
;
2015-12-02 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H14 Cu F12 N3 O4 P'
_chemical_formula_sum            'C25 H14 Cu F12 N3 O4 P'
_chemical_formula_weight         742.89

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.5272(11)
_cell_length_b                   15.4345(14)
_cell_length_c                   14.5163(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.306(3)
_cell_angle_gamma                90
_cell_volume                     2802.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      5
_cell_measurement_theta_max      60

_exptl_crystal_description       prizm
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_F_000             1468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.955
_shelx_estimated_absorpt_T_min   0.647
_shelx_estimated_absorpt_T_max   0.810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6470
_exptl_absorpt_correction_T_max  0.8100
_exptl_absorpt_process_details   ?
_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  'Bruker D8 VENTURE PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            202919
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.928
_diffrn_reflns_theta_max         30.067
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8228
_reflns_number_gt                7037
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0391P)²+2.5641P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8228
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0881
_refine_ls_wR_factor_gt          0.0830
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.74848(2) 0.13848(2) 0.90411(2) 0.01374(5) Uani 1 1 d . . . A 1
P1 P 0.73637(3) -0.07706(3) 0.86028(3) 0.01645(8) Uani 1 1 d . . . B 1
O1 O 0.86553(9) 0.22376(8) 0.90098(8) 0.0174(2) Uani 1 1 d . . . A 1
O2 O 0.69645(9) 0.19824(7) 1.01415(8) 0.0184(2) Uani 1 1 d . . . A 1
F6 F 0.57068(10) 0.26674(7) 1.13192(9) 0.0335(3) Uani 1 1 d . . . C 1
F4 F 0.63275(9) 0.39398(7) 1.10883(8) 0.0306(2) Uani 1 1 d . . . D 1
F5 F 0.72434(11) 0.30333(11) 1.19309(8) 0.0466(4) Uani 1 1 d . . . E 1
F10 F 0.65663(9) 0.20641(9) 0.62565(8) 0.0367(3) Uani 1 1 d . . . F 1
F7 F 0.27737(11) 0.37683(11) 0.79093(9) 0.0511(4) Uani 1 1 d . . . G 1
F8 F 0.27190(12) 0.29472(11) 0.90867(15) 0.0696(6) Uani 1 1 d . . . H 1
F9 F 0.32342(11) 0.42543(9) 0.92435(10) 0.0457(3) Uani 1 1 d . . . I 1
O3 O 0.64879(9) 0.24529(8) 0.80553(8) 0.0182(2) Uani 1 1 d . . . J 1
F11 F 0.49281(11) 0.23355(12) 0.60067(9) 0.0548(4) Uani 1 1 d . . . K 1
F12 F 0.5437(2) 0.11829(10) 0.67540(11) 0.0780(7) Uani 1 1 d . . . L 1
F1 F 0.92750(19) 0.3783(2) 0.81660(15) 0.0575(11) Uani 0.733(6) 1 d . . P M 1
C14 C 0.84175(12) 0.13184(11) 0.72452(11) 0.0169(3) Uani 1 1 d . . . . .
C5 C 0.87891(13) 0.09735(11) 0.64356(11) 0.0191(3) Uani 1 1 d . . . . .
O4 O 0.50347(10) 0.33190(9) 0.93344(8) 0.0236(3) Uani 1 1 d . . . . .
C16 C 0.86065(12) 0.29906(10) 0.93412(11) 0.0170(3) Uani 1 1 d . . . . .
F2 F 1.04086(13) 0.32333(14) 0.91331(19) 0.0431(8) Uani 0.733(6) 1 d . . P M 1
N3 N 0.80088(10) 0.08226(9) 0.78983(9) 0.0147(2) Uani 1 1 d . . . . .
C1 C 0.78893(13) 0.33132(11) 0.99494(12) 0.0196(3) Uani 1 1 d . . . . .
H1 H 0.7897 0.3912 1.0102 0.023 Uiso 1 1 calc R U . . .
C2 C 0.71594(13) 0.27614(10) 1.03362(11) 0.0177(3) Uani 1 1 d . . . . .
C3 C 0.65905(15) 0.31058(12) 1.11711(12) 0.0238(3) Uani 1 1 d . . . . .
C4 C 0.94808(14) 0.35970(11) 0.90175(12) 0.0223(3) Uani 1 1 d . . . . .
F3 F 0.9521(3) 0.43308(15) 0.9500(2) 0.0649(12) Uani 0.733(6) 1 d . . P M 1
C6 C 0.87470(13) 0.00877(12) 0.63025(11) 0.0200(3) Uani 1 1 d . . . . .
H11 H 0.9004 -0.0164 0.5760 0.024 Uiso 1 1 calc R U . . .
C7 C 0.83231(13) -0.04301(11) 0.69746(11) 0.0176(3) Uani 1 1 d . . . . .
H10 H 0.8283 -0.1040 0.6895 0.021 Uiso 1 1 calc R U . . .
C8 C 0.79572(12) -0.00462(10) 0.77647(10) 0.0144(3) Uani 1 1 d . . . . .
C9 C 0.61169(13) -0.01699(11) 0.87608(10) 0.0170(3) Uani 1 1 d . . . . .
C10 C 0.51618(14) -0.06297(12) 0.86619(11) 0.0226(3) Uani 1 1 d . . . . .
H5 H 0.5169 -0.1234 0.8538 0.027 Uiso 1 1 calc R U . . .
C11 C 0.41996(14) -0.02016(14) 0.87453(12) 0.0284(4) Uani 1 1 d . . . . .
H2 H 0.3540 -0.0505 0.8669 0.034 Uiso 1 1 calc R U . . .
C12 C 0.42178(14) 0.06763(14) 0.89424(12) 0.0262(4) Uani 1 1 d . . . . .
H3 H 0.3570 0.0987 0.8996 0.031 Uiso 1 1 calc R U . . .
C13 C 0.51988(13) 0.10965(12) 0.90602(11) 0.0198(3) Uani 1 1 d . . . . .
H4 H 0.5211 0.1694 0.9218 0.024 Uiso 1 1 calc R U . . .
N2 N 0.61285(10) 0.06862(9) 0.89581(9) 0.0159(2) Uani 1 1 d . . . . .
C15 C 0.81430(12) -0.04905(10) 0.96833(10) 0.0153(3) Uani 1 1 d . . . . .
N1 N 0.82929(10) 0.03452(9) 0.99252(9) 0.0163(3) Uani 1 1 d . . . . .
C17 C 0.88432(13) 0.05176(11) 1.07230(11) 0.0195(3) Uani 1 1 d . . . . .
H9 H 0.8956 0.1106 1.0894 0.023 Uiso 1 1 calc R U . . .
C18 C 0.92566(13) -0.01245(12) 1.13124(12) 0.0228(3) Uani 1 1 d . . . . .
H8 H 0.9632 0.0023 1.1878 0.027 Uiso 1 1 calc R U . . .
C19 C 0.91100(13) -0.09826(12) 1.10597(12) 0.0228(3) Uani 1 1 d . . . . .
H7 H 0.9390 -0.1435 1.1446 0.027 Uiso 1 1 calc R U . . .
C20 C 0.85447(13) -0.11705(11) 1.02294(11) 0.0187(3) Uani 1 1 d . . . . .
H6 H 0.8435 -0.1754 1.0039 0.022 Uiso 1 1 calc R U . . .
C21 C 0.56312(15) 0.20131(12) 0.66449(12) 0.0245(3) Uani 1 1 d . . . . .
C22 C 0.56339(13) 0.24955(11) 0.75744(11) 0.0179(3) Uani 1 1 d . . . . .
C23 C 0.46640(13) 0.28882(11) 0.77634(11) 0.0197(3) Uani 1 1 d . . . . .
H14 H 0.4117 0.2911 0.7283 0.024 Uiso 1 1 calc R U . . .
C24 C 0.44492(13) 0.32529(11) 0.86241(12) 0.0189(3) Uani 1 1 d . . . . .
C25 C 0.32862(15) 0.35672(12) 0.87089(13) 0.0251(3) Uani 1 1 d . . . . .
H12 H 0.9053(18) 0.1340(14) 0.6010(16) 0.024(6) Uiso 1 1 d . . . . .
H13 H 0.8425(17) 0.1921(14) 0.7377(14) 0.020(5) Uiso 1 1 d . . . . .
F1' F 1.0113(5) 0.3241(3) 0.8326(6) 0.062(3) Uani 0.267(6) 1 d . . P M 2
F2' F 1.0210(7) 0.3850(7) 0.9598(4) 0.077(5) Uani 0.267(6) 1 d . . P M 2
F3' F 0.9149(4) 0.4310(4) 0.8579(7) 0.052(3) Uani 0.267(6) 1 d . . P M 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9729(11) . ?
Cu1 O2 1.9867(12) . ?
Cu1 N2 2.0101(13) . ?
Cu1 N3 2.0152(13) . ?
Cu1 N1 2.2575(14) . ?
P1 C8 1.8405(16) . ?
P1 C9 1.8420(17) . ?
P1 C15 1.8502(16) . ?
O1 C16 1.261(2) . ?
O2 C2 1.256(2) . ?
F6 C3 1.326(2) . ?
F4 C3 1.332(2) . ?
F5 C3 1.339(2) . ?
F10 C21 1.331(2) . ?
F7 C25 1.330(2) . ?
F8 C25 1.329(2) . ?
F9 C25 1.318(2) . ?
O3 C22 1.2451(19) . ?
F11 C21 1.337(2) . ?
F12 C21 1.315(2) . ?
F1 C4 1.281(2) . ?
C14 N3 1.343(2) . ?
C14 C5 1.394(2) . ?
C14 H13 0.95(2) . ?
C5 C6 1.381(2) . ?
C5 H12 0.91(2) . ?
O4 C24 1.235(2) . ?
C16 C1 1.388(2) . ?
C16 C4 1.535(2) . ?
F2 C4 1.293(2) . ?
N3 C8 1.356(2) . ?
C1 C2 1.391(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.536(2) . ?
C4 F2' 1.268(5) . ?
C4 F3' 1.327(5) . ?
C4 F3 1.331(3) . ?
C4 F1' 1.425(6) . ?
C6 C7 1.390(2) . ?
C6 H11 0.9500 . ?
C7 C8 1.392(2) . ?
C7 H10 0.9500 . ?
C9 N2 1.352(2) . ?
C9 C10 1.391(2) . ?
C10 C11 1.386(3) . ?
C10 H5 0.9500 . ?
C11 C12 1.385(3) . ?
C11 H2 0.9500 . ?
C12 C13 1.391(2) . ?
C12 H3 0.9500 . ?
C13 N2 1.341(2) . ?
C13 H4 0.9500 . ?
C15 N1 1.347(2) . ?
C15 C20 1.392(2) . ?
N1 C17 1.340(2) . ?
C17 C18 1.390(2) . ?
C17 H9 0.9500 . ?
C18 C19 1.384(3) . ?
C18 H8 0.9500 . ?
C19 C20 1.393(2) . ?
C19 H7 0.9500 . ?
C20 H6 0.9500 . ?
C21 C22 1.541(2) . ?
C22 C23 1.399(2) . ?
C23 C24 1.410(2) . ?
C23 H14 0.9500 . ?
C24 C25 1.547(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 89.29(5) . . ?
O1 Cu1 N2 169.51(5) . . ?
O2 Cu1 N2 88.96(5) . . ?
O1 Cu1 N3 89.45(5) . . ?
O2 Cu1 N3 177.78(5) . . ?
N2 Cu1 N3 91.95(5) . . ?
O1 Cu1 N1 100.24(5) . . ?
O2 Cu1 N1 91.72(5) . . ?
N2 Cu1 N1 90.15(5) . . ?
N3 Cu1 N1 90.30(5) . . ?
C8 P1 C9 98.88(7) . . ?
C8 P1 C15 101.83(7) . . ?
C9 P1 C15 100.75(7) . . ?
C16 O1 Cu1 123.63(11) . . ?
C2 O2 Cu1 123.84(11) . . ?
N3 C14 C5 122.48(15) . . ?
N3 C14 H13 114.6(13) . . ?
C5 C14 H13 122.9(13) . . ?
C6 C5 C14 118.93(15) . . ?
C6 C5 H12 122.1(14) . . ?
C14 C5 H12 119.0(14) . . ?
O1 C16 C1 128.38(15) . . ?
O1 C16 C4 113.21(15) . . ?
C1 C16 C4 118.40(15) . . ?
C14 N3 C8 118.66(14) . . ?
C14 N3 Cu1 119.44(11) . . ?
C8 N3 Cu1 121.90(11) . . ?
C16 C1 C2 120.12(15) . . ?
C16 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
O2 C2 C1 128.24(16) . . ?
O2 C2 C3 114.58(15) . . ?
C1 C2 C3 116.89(15) . . ?
F6 C3 F4 107.66(14) . . ?
F6 C3 F5 107.45(16) . . ?
F4 C3 F5 106.93(15) . . ?
F6 C3 C2 112.40(15) . . ?
F4 C3 C2 112.75(15) . . ?
F5 C3 C2 109.37(14) . . ?
F1 C4 F2 110.6(2) . . ?
F2' C4 F3' 104.9(6) . . ?
F1 C4 F3 108.4(2) . . ?
F2 C4 F3 107.2(2) . . ?
F2' C4 F1' 100.3(6) . . ?
F3' C4 F1' 98.9(5) . . ?
F2' C4 C16 118.9(3) . . ?
F1 C4 C16 108.95(16) . . ?
F2 C4 C16 110.34(15) . . ?
F3' C4 C16 116.3(3) . . ?
F3 C4 C16 111.33(16) . . ?
F1' C4 C16 114.6(2) . . ?
C5 C6 C7 118.94(15) . . ?
C5 C6 H11 120.5 . . ?
C7 C6 H11 120.5 . . ?
C6 C7 C8 119.40(15) . . ?
C6 C7 H10 120.3 . . ?
C8 C7 H10 120.3 . . ?
N3 C8 C7 121.58(14) . . ?
N3 C8 P1 121.59(11) . . ?
C7 C8 P1 116.80(12) . . ?
N2 C9 C10 121.27(16) . . ?
N2 C9 P1 121.29(11) . . ?
C10 C9 P1 117.43(13) . . ?
C11 C10 C9 119.66(17) . . ?
C11 C10 H5 120.2 . . ?
C9 C10 H5 120.2 . . ?
C12 C11 C10 118.72(16) . . ?
C12 C11 H2 120.6 . . ?
C10 C11 H2 120.6 . . ?
C11 C12 C13 119.03(17) . . ?
C11 C12 H3 120.5 . . ?
C13 C12 H3 120.5 . . ?
N2 C13 C12 122.19(17) . . ?
N2 C13 H4 118.9 . . ?
C12 C13 H4 118.9 . . ?
C13 N2 C9 119.08(14) . . ?
C13 N2 Cu1 118.45(12) . . ?
C9 N2 Cu1 122.40(11) . . ?
N1 C15 C20 122.22(14) . . ?
N1 C15 P1 120.23(11) . . ?
C20 C15 P1 117.54(12) . . ?
C17 N1 C15 118.20(14) . . ?
C17 N1 Cu1 122.80(11) . . ?
C15 N1 Cu1 118.76(10) . . ?
N1 C17 C18 123.05(16) . . ?
N1 C17 H9 118.5 . . ?
C18 C17 H9 118.5 . . ?
C19 C18 C17 118.71(15) . . ?
C19 C18 H8 120.6 . . ?
C17 C18 H8 120.6 . . ?
C18 C19 C20 118.81(16) . . ?
C18 C19 H7 120.6 . . ?
C20 C19 H7 120.6 . . ?
C15 C20 C19 119.01(16) . . ?
C15 C20 H6 120.5 . . ?
C19 C20 H6 120.5 . . ?
F12 C21 F10 106.38(18) . . ?
F12 C21 F11 109.08(18) . . ?
F10 C21 F11 104.18(15) . . ?
F12 C21 C22 110.87(15) . . ?
F10 C21 C22 112.63(14) . . ?
F11 C21 C22 113.27(15) . . ?
O3 C22 C23 129.86(15) . . ?
O3 C22 C21 115.08(15) . . ?
C23 C22 C21 115.02(14) . . ?
C22 C23 C24 123.97(15) . . ?
C22 C23 H14 118.0 . . ?
C24 C23 H14 118.0 . . ?
O4 C24 C23 129.67(16) . . ?
O4 C24 C25 115.11(15) . . ?
C23 C24 C25 115.10(14) . . ?
F9 C25 F8 106.89(18) . . ?
F9 C25 F7 106.75(16) . . ?
F8 C25 F7 106.59(18) . . ?
F9 C25 C24 112.21(15) . . ?
F8 C25 C24 109.60(15) . . ?
F7 C25 C24 114.40(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C14 C5 C6 -0.7(2) . . . . ?
Cu1 O1 C16 C1 15.7(2) . . . . ?
Cu1 O1 C16 C4 -165.26(10) . . . . ?
C5 C14 N3 C8 0.1(2) . . . . ?
C5 C14 N3 Cu1 -179.64(12) . . . . ?
O1 C16 C1 C2 6.0(3) . . . . ?
C4 C16 C1 C2 -173.06(14) . . . . ?
Cu1 O2 C2 C1 -11.8(2) . . . . ?
Cu1 O2 C2 C3 174.75(10) . . . . ?
C16 C1 C2 O2 -8.1(3) . . . . ?
C16 C1 C2 C3 165.26(14) . . . . ?
O2 C2 C3 F6 -24.7(2) . . . . ?
C1 C2 C3 F6 161.07(15) . . . . ?
O2 C2 C3 F4 -146.57(15) . . . . ?
C1 C2 C3 F4 39.2(2) . . . . ?
O2 C2 C3 F5 94.61(18) . . . . ?
C1 C2 C3 F5 -79.67(19) . . . . ?
C1 C16 C4 F2' 67.4(7) . . . . ?
O1 C16 C4 F1 71.3(3) . . . . ?
C1 C16 C4 F1 -109.5(3) . . . . ?
O1 C16 C4 F2 -50.3(2) . . . . ?
C1 C16 C4 F2 128.9(2) . . . . ?
C1 C16 C4 F3' -59.5(5) . . . . ?
O1 C16 C4 F3 -169.1(2) . . . . ?
C1 C16 C4 F3 10.0(3) . . . . ?
C1 C16 C4 F1' -174.1(4) . . . . ?
C14 C5 C6 C7 0.8(2) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C14 N3 C8 C7 0.5(2) . . . . ?
Cu1 N3 C8 C7 -179.84(11) . . . . ?
C14 N3 C8 P1 -177.69(11) . . . . ?
Cu1 N3 C8 P1 2.01(17) . . . . ?
C6 C7 C8 N3 -0.3(2) . . . . ?
C6 C7 C8 P1 177.90(12) . . . . ?
C9 P1 C8 N3 48.04(13) . . . . ?
C15 P1 C8 N3 -55.00(14) . . . . ?
C9 P1 C8 C7 -130.19(12) . . . . ?
C15 P1 C8 C7 126.76(12) . . . . ?
C8 P1 C9 N2 -50.80(14) . . . . ?
C15 P1 C9 N2 53.14(14) . . . . ?
C8 P1 C9 C10 128.70(13) . . . . ?
C15 P1 C9 C10 -127.37(13) . . . . ?
N2 C9 C10 C11 1.5(2) . . . . ?
P1 C9 C10 C11 -177.98(13) . . . . ?
C9 C10 C11 C12 -1.1(3) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C11 C12 C13 N2 2.3(3) . . . . ?
C12 C13 N2 C9 -2.0(2) . . . . ?
C12 C13 N2 Cu1 174.93(12) . . . . ?
C10 C9 N2 C13 0.0(2) . . . . ?
P1 C9 N2 C13 179.51(11) . . . . ?
C10 C9 N2 Cu1 -176.75(11) . . . . ?
P1 C9 N2 Cu1 2.73(17) . . . . ?
C8 P1 C15 N1 47.79(14) . . . . ?
C9 P1 C15 N1 -53.76(14) . . . . ?
C8 P1 C15 C20 -133.13(13) . . . . ?
C9 P1 C15 C20 125.32(13) . . . . ?
C20 C15 N1 C17 -0.4(2) . . . . ?
P1 C15 N1 C17 178.62(12) . . . . ?
C20 C15 N1 Cu1 -174.93(12) . . . . ?
P1 C15 N1 Cu1 4.10(17) . . . . ?
C15 N1 C17 C18 -0.5(2) . . . . ?
Cu1 N1 C17 C18 173.75(12) . . . . ?
N1 C17 C18 C19 1.1(3) . . . . ?
C17 C18 C19 C20 -0.7(3) . . . . ?
N1 C15 C20 C19 0.8(2) . . . . ?
P1 C15 C20 C19 -178.27(13) . . . . ?
C18 C19 C20 C15 -0.2(2) . . . . ?
F12 C21 C22 O3 82.5(2) . . . . ?
F10 C21 C22 O3 -36.6(2) . . . . ?
F11 C21 C22 O3 -154.53(16) . . . . ?
F12 C21 C22 C23 -95.3(2) . . . . ?
F10 C21 C22 C23 145.58(16) . . . . ?
F11 C21 C22 C23 27.7(2) . . . . ?
O3 C22 C23 C24 -6.8(3) . . . . ?
C21 C22 C23 C24 170.57(16) . . . . ?
C22 C23 C24 O4 1.9(3) . . . . ?
C22 C23 C24 C25 -173.95(16) . . . . ?
O4 C24 C25 F9 36.8(2) . . . . ?
C23 C24 C25 F9 -146.72(16) . . . . ?
O4 C24 C25 F8 -81.8(2) . . . . ?
C23 C24 C25 F8 94.7(2) . . . . ?
O4 C24 C25 F7 158.57(17) . . . . ?
C23 C24 C25 F7 -24.9(2) . . . . ?

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
C14 H13 O1 0.95(2) 2.42(2) 2.928(2) 113.2(16) .
C5 H12 F6 0.91(2) 2.59(2) 3.201(2) 124.4(18) 4_665
C20 H6 F10 0.95 2.62 3.473(2) 149.7 2_646
C13 H4 O4 0.95 2.52 3.461(2) 168.6 .
C10 H5 F6 0.95 2.48 3.329(2) 148.2 3_657
C7 H10 O3 0.95 2.34 3.277(2) 167.1 2_646
C14 H13 O1 0.95(2) 2.42(2) 2.928(2) 113.2(16) .
C5 H12 F6 0.91(2) 2.59(2) 3.201(2) 124.4(18) 4_665
C20 H6 F10 0.95 2.62 3.473(2) 149.7 2_646
C13 H4 O4 0.95 2.52 3.461(2) 168.6 .
C10 H5 F6 0.95 2.48 3.329(2) 148.2 3_657
C7 H10 O3 0.95 2.34 3.277(2) 167.1 2_646
C14 H13 O1 0.95(2) 2.42(2) 2.928(2) 113.2(16) .
C20 H6 F10 0.95 2.62 3.473(2) 149.7 2_646
C13 H4 O4 0.95 2.52 3.461(2) 168.6 .
C10 H5 F6 0.95 2.48 3.329(2) 148.2 3_657
C7 H10 O3 0.95 2.34 3.277(2) 167.1 2_646
C14 H13 O1 0.95(2) 2.42(2) 2.928(2) 113.2(16) .
C13 H4 O4 0.95 2.52 3.461(2) 168.6 .
C7 H10 O3 0.95 2.34 3.277(2) 167.1 2_646
C14 H13 O1 0.95(2) 2.42(2) 2.928(2) 113.2(16) .
C13 H4 O4 0.95 2.52 3.461(2) 168.6 .
C7 H10 O3 0.95 2.34 3.277(2) 167.1 2_646
C6 H11 O4 0.95 2.64 3.286(2) 125.6 2_646
C6 H11 O4 0.95 2.64 3.286(2) 125.6 2_646
C7 H10 O3 0.95 2.34 3.277(2) 167.1 2_646
C13 H4 O4 0.95 2.52 3.461(2) 168.6 .
C7 H10 O3 0.95 2.34 3.277(2) 167.1 2_646
C13 H4 O4 0.95 2.52 3.461(2) 168.6 .
C14 H13 O1 0.95(2) 2.42(2) 2.928(2) 113.2(16) .
C7 H10 O3 0.95 2.34 3.277(2) 167.1 2_646
C13 H4 O4 0.95 2.52 3.461(2) 168.6 .
C14 H13 O1 0.95(2) 2.42(2) 2.928(2) 113.2(16) .
C7 H10 O3 0.95 2.34 3.277(2) 167.1 2_646
C10 H5 F6 0.95 2.48 3.329(2) 148.2 3_657
C13 H4 O4 0.95 2.52 3.461(2) 168.6 .
C20 H6 F10 0.95 2.62 3.473(2) 149.7 2_646
C14 H13 O1 0.95(2) 2.42(2) 2.928(2) 113.2(16) .
C7 H10 O3 0.95 2.34 3.277(2) 167.1 2_646
C10 H5 F6 0.95 2.48 3.329(2) 148.2 3_657
C13 H4 O4 0.95 2.52 3.461(2) 168.6 .
C20 H6 F10 0.95 2.62 3.473(2) 149.7 2_646
C5 H12 F6 0.91(2) 2.59(2) 3.201(2) 124.4(18) 4_665

_refine_diff_density_max         0.682
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.078

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1431159'
_audit_update_record             
;
2015-10-14 deposited with the CCDC.
2017-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          450
_chemical_formula_moiety         'C25 H14 Cu F12 N3 O5 P'
_chemical_formula_sum            'C25 H14 Cu F12 N3 O5 P'
_chemical_formula_weight         758.89

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.515(2)
_cell_length_b                   15.165(3)
_cell_length_c                   14.627(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.549(7)
_cell_angle_gamma                90
_cell_volume                     2767.2(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prizm
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.824
_exptl_crystal_F_000             1508
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.973
_shelx_estimated_absorpt_T_min   0.642
_shelx_estimated_absorpt_T_max   0.793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.621
_exptl_absorpt_correction_T_max  0.784
_exptl_absorpt_process_details   ?

_exptl_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            187370
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0887
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.231
_diffrn_reflns_theta_max         30.093
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8123
_reflns_number_gt                6573
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0617P)²+9.4334P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     shelx
_refine_ls_extinction_coef       2.17
_refine_ls_number_reflns         8123
_refine_ls_number_parameters     428
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1424
_refine_ls_wR_factor_gt          0.1315
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.24481(3) 0.14210(2) 0.40310(2) 0.01174(9) Uani 1 1 d . . . . .
P1 P 0.23795(6) -0.07253(4) 0.36018(5) 0.01364(14) Uani 1 1 d . . . . .
O1 O 0.36207(15) 0.22840(13) 0.40011(13) 0.0152(4) Uani 1 1 d . . . . .
O2 O 0.19723(16) 0.20106(13) 0.51288(13) 0.0156(4) Uani 1 1 d . . . . .
F3 F 0.07285(17) 0.26906(12) 0.62863(14) 0.0288(4) Uani 1 1 d . . . . .
F4 F 0.13067(16) 0.39971(12) 0.60497(14) 0.0284(4) Uani 1 1 d . . . . .
F5 F 0.22658(18) 0.30989(18) 0.68993(14) 0.0427(6) Uani 1 1 d . . . . .
O6 O 0.13490(15) 0.24219(13) 0.30996(13) 0.0159(4) Uani 1 1 d . . . . .
F7 F -0.2288(2) 0.3915(2) 0.29428(15) 0.0555(8) Uani 1 1 d . . . . .
F8 F -0.2429(2) 0.29405(18) 0.3970(3) 0.0668(10) Uani 1 1 d . . . . .
F9 F -0.18967(18) 0.42313(16) 0.43405(15) 0.0388(5) Uani 1 1 d . . . . .
F10 F 0.13174(17) 0.16763(18) 0.14544(15) 0.0417(6) Uani 1 1 d . . . . .
F11 F -0.0267(2) 0.12795(14) 0.17324(15) 0.0383(5) Uani 1 1 d . . . . .
F12 F -0.00246(17) 0.24787(14) 0.10062(12) 0.0291(4) Uani 1 1 d . . . . .
F2 F 0.4078(2) 0.4345(2) 0.3573(3) 0.0785(12) Uani 1 1 d . . . . .
F1 F 0.5107(3) 0.3925(3) 0.4681(2) 0.115(2) Uani 1 1 d . . . . .
C25 C 0.3764(2) 0.10136(19) 0.14688(19) 0.0160(5) Uani 1 1 d . . . . .
O4 O 0.22729(19) -0.16611(14) 0.33537(16) 0.0248(5) Uani 1 1 d . . . . .
O5 O -0.00565(18) 0.33535(15) 0.43647(14) 0.0222(4) Uani 1 1 d . . . . .
C2 C 0.3579(2) 0.30491(18) 0.43256(19) 0.0156(5) Uani 1 1 d . . . . .
N2 N 0.29825(17) 0.08504(15) 0.29035(15) 0.0120(4) Uani 1 1 d . . . . .
N3 N 0.11002(18) 0.06730(15) 0.39663(15) 0.0132(4) Uani 1 1 d . . . . .
N4 N 0.32956(18) 0.03168(15) 0.49475(16) 0.0139(4) Uani 1 1 d . . . . .
C1 C 0.4463(2) 0.36781(19) 0.4030(2) 0.0203(6) Uani 1 1 d . . . . .
F6 F 0.5078(3) 0.3296(2) 0.3436(4) 0.0990(16) Uani 1 1 d . . . . .
C3 C 0.2868(2) 0.33763(18) 0.4927(2) 0.0170(5) Uani 1 1 d . . . . .
H1 H 0.2867 0.3974 0.5068 0.020 Uiso 1 1 calc R U . . .
C4 C 0.2158(2) 0.28085(18) 0.53167(18) 0.0152(5) Uani 1 1 d . . . . .
C5 C 0.1598(2) 0.3155(2) 0.6142(2) 0.0198(6) Uani 1 1 d . . . . .
C6 C 0.3366(2) 0.13623(18) 0.22561(18) 0.0138(5) Uani 1 1 d . . . . .
H12 H 0.3367 0.1971 0.2335 0.017 Uiso 1 1 calc R U . . .
C7 C 0.3772(2) 0.01084(19) 0.13462(18) 0.0164(5) Uani 1 1 d . . . . .
H2 H 0.4046 -0.0136 0.0831 0.020 Uiso 1 1 calc R U . . .
C8 C 0.3365(2) -0.04295(18) 0.20067(18) 0.0140(5) Uani 1 1 d . . . . .
H11 H 0.3353 -0.1039 0.1939 0.017 Uiso 1 1 calc R U . . .
C9 C 0.2975(2) -0.00332(17) 0.27702(17) 0.0124(5) Uani 1 1 d . . . . .
C10 C 0.1105(2) -0.01917(18) 0.37380(17) 0.0141(5) Uani 1 1 d . . . . .
C11 C 0.0154(2) 0.1054(2) 0.40917(18) 0.0167(5) Uani 1 1 d . . . . .
H6 H 0.0144 0.1641 0.4275 0.020 Uiso 1 1 calc R U . . .
C12 C -0.0812(2) 0.0600(2) 0.3957(2) 0.0220(6) Uani 1 1 d . . . . .
H5 H -0.1457 0.0887 0.4029 0.026 Uiso 1 1 calc R U . . .
C13 C -0.0806(2) -0.0278(2) 0.3714(2) 0.0244(6) Uani 1 1 d . . . . .
H4 H -0.1445 -0.0591 0.3622 0.029 Uiso 1 1 calc R U . . .
C14 C 0.0174(2) -0.0689(2) 0.36098(19) 0.0199(6) Uani 1 1 d . . . . .
H3 H 0.0203 -0.1283 0.3457 0.024 Uiso 1 1 calc R U . . .
C15 C 0.3160(2) -0.05332(17) 0.46860(18) 0.0133(5) Uani 1 1 d . . . . .
C16 C 0.3830(2) 0.04681(19) 0.57561(19) 0.0179(5) Uani 1 1 d . . . . .
H10 H 0.3935 0.1049 0.5946 0.021 Uiso 1 1 calc R U . . .
C17 C 0.4238(2) -0.0205(2) 0.6331(2) 0.0221(6) Uani 1 1 d . . . . .
H9 H 0.4596 -0.0073 0.6896 0.026 Uiso 1 1 calc R U . . .
C18 C 0.4104(2) -0.1069(2) 0.6051(2) 0.0230(6) Uani 1 1 d . . . . .
H8 H 0.4376 -0.1529 0.6422 0.028 Uiso 1 1 calc R U . . .
C19 C 0.3556(2) -0.12427(19) 0.5204(2) 0.0176(5) Uani 1 1 d . . . . .
H7 H 0.3459 -0.1818 0.4993 0.021 Uiso 1 1 calc R U . . .
C20 C 0.0484(2) 0.24738(18) 0.26230(18) 0.0146(5) Uani 1 1 d . . . . .
C21 C -0.0468(2) 0.29045(19) 0.28064(19) 0.0171(5) Uani 1 1 d . . . . .
H13 H -0.1010 0.2943 0.2335 0.021 Uiso 1 1 calc R U . . .
C22 C -0.0658(2) 0.32831(19) 0.36595(19) 0.0168(5) Uani 1 1 d . . . . .
C23 C -0.1823(2) 0.3604(2) 0.3727(2) 0.0211(6) Uani 1 1 d . . . . .
C24 C 0.0393(2) 0.1974(2) 0.17012(19) 0.0183(5) Uani 1 1 d . . . . .
H14 H 0.400(3) 0.140(2) 0.106(3) 0.019(9) 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 O1 1.9694(19) . ?
Cu1 O2 1.971(2) . ?
Cu1 N2 2.023(2) . ?
Cu1 N3 2.029(2) . ?
Cu1 N4 2.345(2) . ?
Cu1 O6 2.3988(19) . ?
P1 O4 1.468(2) . ?
P1 C9 1.811(3) . ?
P1 C10 1.814(3) . ?
P1 C15 1.819(3) . ?
O1 C2 1.256(3) . ?
O2 C4 1.258(3) . ?
F3 C5 1.328(4) . ?
F4 C5 1.331(3) . ?
F5 C5 1.336(3) . ?
O6 C20 1.242(3) . ?
F7 C23 1.331(4) . ?
F8 C23 1.325(4) . ?
F9 C23 1.316(4) . ?
F10 C24 1.319(3) . ?
F11 C24 1.341(4) . ?
F12 C24 1.345(3) . ?
F2 C1 1.285(4) . ?
F1 C1 1.255(4) . ?
C25 C7 1.385(4) . ?
C25 C6 1.394(4) . ?
C25 H14 0.91(4) . ?
O5 C22 1.233(3) . ?
C2 C3 1.392(4) . ?
C2 C1 1.548(4) . ?
N2 C6 1.342(3) . ?
N2 C9 1.354(3) . ?
N3 C11 1.343(4) . ?
N3 C10 1.353(4) . ?
N4 C16 1.331(4) . ?
N4 C15 1.352(3) . ?
C1 F6 1.338(4) . ?
C3 C4 1.392(4) . ?
C3 H1 0.9300 . ?
C4 C5 1.535(4) . ?
C6 H12 0.9300 . ?
C7 C8 1.392(4) . ?
C7 H2 0.9300 . ?
C8 C9 1.390(4) . ?
C8 H11 0.9300 . ?
C10 C14 1.387(4) . ?
C11 C12 1.392(4) . ?
C11 H6 0.9300 . ?
C12 C13 1.377(5) . ?
C12 H5 0.9300 . ?
C13 C14 1.396(5) . ?
C13 H4 0.9300 . ?
C14 H3 0.9300 . ?
C15 C19 1.385(4) . ?
C16 C17 1.394(4) . ?
C16 H10 0.9300 . ?
C17 C18 1.380(5) . ?
C17 H9 0.9300 . ?
C18 C19 1.393(4) . ?
C18 H8 0.9300 . ?
C19 H7 0.9300 . ?
C20 C21 1.404(4) . ?
C20 C24 1.543(4) . ?
C21 C22 1.411(4) . ?
C21 H13 0.9300 . ?
C22 C23 1.547(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 89.45(8) . . ?
O1 Cu1 N2 88.34(9) . . ?
O2 Cu1 N2 177.79(9) . . ?
O1 Cu1 N3 171.42(9) . . ?
O2 Cu1 N3 89.30(9) . . ?
N2 Cu1 N3 92.88(9) . . ?
O1 Cu1 N4 100.55(8) . . ?
O2 Cu1 N4 90.59(8) . . ?
N2 Cu1 N4 89.82(8) . . ?
N3 Cu1 N4 87.94(9) . . ?
O1 Cu1 O6 87.80(8) . . ?
O2 Cu1 O6 88.79(8) . . ?
N2 Cu1 O6 91.12(8) . . ?
N3 Cu1 O6 83.69(8) . . ?
N4 Cu1 O6 171.62(7) . . ?
O4 P1 C9 115.36(13) . . ?
O4 P1 C10 113.26(13) . . ?
C9 P1 C10 103.15(12) . . ?
O4 P1 C15 113.72(13) . . ?
C9 P1 C15 105.77(12) . . ?
C10 P1 C15 104.41(12) . . ?
C2 O1 Cu1 123.53(18) . . ?
C4 O2 Cu1 123.48(18) . . ?
C20 O6 Cu1 142.51(18) . . ?
C7 C25 C6 119.3(3) . . ?
C7 C25 H14 123(2) . . ?
C6 C25 H14 117(2) . . ?
O1 C2 C3 128.0(3) . . ?
O1 C2 C1 114.3(2) . . ?
C3 C2 C1 117.6(2) . . ?
C6 N2 C9 118.0(2) . . ?
C6 N2 Cu1 119.19(18) . . ?
C9 N2 Cu1 122.81(18) . . ?
C11 N3 C10 118.1(2) . . ?
C11 N3 Cu1 119.46(19) . . ?
C10 N3 Cu1 122.26(18) . . ?
C16 N4 C15 117.3(2) . . ?
C16 N4 Cu1 123.86(19) . . ?
C15 N4 Cu1 118.56(17) . . ?
F1 C1 F2 110.6(4) . . ?
F1 C1 F6 104.7(4) . . ?
F2 C1 F6 102.4(4) . . ?
F1 C1 C2 113.7(3) . . ?
F2 C1 C2 112.6(3) . . ?
F6 C1 C2 112.0(3) . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H1 120.0 . . ?
C2 C3 H1 120.0 . . ?
O2 C4 C3 128.2(3) . . ?
O2 C4 C5 114.4(3) . . ?
C3 C4 C5 117.1(2) . . ?
F3 C5 F4 107.7(2) . . ?
F3 C5 F5 107.5(3) . . ?
F4 C5 F5 107.1(3) . . ?
F3 C5 C4 112.0(2) . . ?
F4 C5 C4 112.8(2) . . ?
F5 C5 C4 109.6(2) . . ?
N2 C6 C25 122.3(2) . . ?
N2 C6 H12 118.8 . . ?
C25 C6 H12 118.8 . . ?
C25 C7 C8 119.0(3) . . ?
C25 C7 H2 120.5 . . ?
C8 C7 H2 120.5 . . ?
C9 C8 C7 118.4(2) . . ?
C9 C8 H11 120.8 . . ?
C7 C8 H11 120.8 . . ?
N2 C9 C8 123.0(2) . . ?
N2 C9 P1 118.38(19) . . ?
C8 C9 P1 118.6(2) . . ?
N3 C10 C14 122.7(3) . . ?
N3 C10 P1 118.70(19) . . ?
C14 C10 P1 118.6(2) . . ?
N3 C11 C12 122.2(3) . . ?
N3 C11 H6 118.9 . . ?
C12 C11 H6 118.9 . . ?
C13 C12 C11 119.5(3) . . ?
C13 C12 H5 120.3 . . ?
C11 C12 H5 120.3 . . ?
C12 C13 C14 118.9(3) . . ?
C12 C13 H4 120.6 . . ?
C14 C13 H4 120.6 . . ?
C10 C14 C13 118.6(3) . . ?
C10 C14 H3 120.7 . . ?
C13 C14 H3 120.7 . . ?
N4 C15 C19 123.7(3) . . ?
N4 C15 P1 116.51(19) . . ?
C19 C15 P1 119.8(2) . . ?
N4 C16 C17 123.0(3) . . ?
N4 C16 H10 118.5 . . ?
C17 C16 H10 118.5 . . ?
C18 C17 C16 119.1(3) . . ?
C18 C17 H9 120.5 . . ?
C16 C17 H9 120.5 . . ?
C17 C18 C19 118.9(3) . . ?
C17 C18 H8 120.6 . . ?
C19 C18 H8 120.6 . . ?
C15 C19 C18 118.0(3) . . ?
C15 C19 H7 121.0 . . ?
C18 C19 H7 121.0 . . ?
O6 C20 C21 129.6(3) . . ?
O6 C20 C24 117.4(2) . . ?
C21 C20 C24 113.0(2) . . ?
C20 C21 C22 124.3(3) . . ?
C20 C21 H13 117.8 . . ?
C22 C21 H13 117.8 . . ?
O5 C22 C21 129.8(3) . . ?
O5 C22 C23 115.8(3) . . ?
C21 C22 C23 114.2(2) . . ?
F9 C23 F8 107.1(3) . . ?
F9 C23 F7 106.4(3) . . ?
F8 C23 F7 106.2(3) . . ?
F9 C23 C22 112.9(3) . . ?
F8 C23 C22 109.9(3) . . ?
F7 C23 C22 113.9(3) . . ?
F10 C24 F11 107.2(3) . . ?
F10 C24 F12 106.5(2) . . ?
F11 C24 F12 105.6(2) . . ?
F10 C24 C20 113.7(2) . . ?
F11 C24 C20 111.1(2) . . ?
F12 C24 C20 112.2(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C2 C3 15.7(4) . . . . ?
Cu1 O1 C2 C1 -166.41(17) . . . . ?
O1 C2 C1 F1 -115.1(4) . . . . ?
C3 C2 C1 F1 63.0(4) . . . . ?
O1 C2 C1 F2 118.2(3) . . . . ?
C3 C2 C1 F2 -63.7(4) . . . . ?
O1 C2 C1 F6 3.4(4) . . . . ?
C3 C2 C1 F6 -178.5(3) . . . . ?
O1 C2 C3 C4 6.9(4) . . . . ?
C1 C2 C3 C4 -170.9(2) . . . . ?
Cu1 O2 C4 C3 -13.2(4) . . . . ?
Cu1 O2 C4 C5 173.06(17) . . . . ?
C2 C3 C4 O2 -8.3(4) . . . . ?
C2 C3 C4 C5 165.3(2) . . . . ?
O2 C4 C5 F3 -24.3(3) . . . . ?
C3 C4 C5 F3 161.2(2) . . . . ?
O2 C4 C5 F4 -145.9(2) . . . . ?
C3 C4 C5 F4 39.6(3) . . . . ?
O2 C4 C5 F5 94.9(3) . . . . ?
C3 C4 C5 F5 -79.6(3) . . . . ?
C9 N2 C6 C25 -0.9(4) . . . . ?
Cu1 N2 C6 C25 178.9(2) . . . . ?
C7 C25 C6 N2 -0.3(4) . . . . ?
C6 C25 C7 C8 1.1(4) . . . . ?
C25 C7 C8 C9 -0.7(4) . . . . ?
C6 N2 C9 C8 1.3(4) . . . . ?
Cu1 N2 C9 C8 -178.45(19) . . . . ?
C6 N2 C9 P1 -176.04(19) . . . . ?
Cu1 N2 C9 P1 4.2(3) . . . . ?
C7 C8 C9 N2 -0.6(4) . . . . ?
C7 C8 C9 P1 176.8(2) . . . . ?
O4 P1 C9 N2 172.4(2) . . . . ?
C10 P1 C9 N2 48.4(2) . . . . ?
C15 P1 C9 N2 -61.0(2) . . . . ?
O4 P1 C9 C8 -5.1(3) . . . . ?
C10 P1 C9 C8 -129.1(2) . . . . ?
C15 P1 C9 C8 121.5(2) . . . . ?
C11 N3 C10 C14 1.5(4) . . . . ?
Cu1 N3 C10 C14 -173.9(2) . . . . ?
C11 N3 C10 P1 -178.06(19) . . . . ?
Cu1 N3 C10 P1 6.5(3) . . . . ?
O4 P1 C10 N3 -180.0(2) . . . . ?
C9 P1 C10 N3 -54.6(2) . . . . ?
C15 P1 C10 N3 55.8(2) . . . . ?
O4 P1 C10 C14 0.5(3) . . . . ?
C9 P1 C10 C14 125.9(2) . . . . ?
C15 P1 C10 C14 -123.8(2) . . . . ?
C10 N3 C11 C12 -2.8(4) . . . . ?
Cu1 N3 C11 C12 172.8(2) . . . . ?
N3 C11 C12 C13 2.1(4) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
N3 C10 C14 C13 0.5(4) . . . . ?
P1 C10 C14 C13 -180.0(2) . . . . ?
C12 C13 C14 C10 -1.2(4) . . . . ?
C16 N4 C15 C19 -0.9(4) . . . . ?
Cu1 N4 C15 C19 -175.2(2) . . . . ?
C16 N4 C15 P1 177.5(2) . . . . ?
Cu1 N4 C15 P1 3.2(3) . . . . ?
O4 P1 C15 N4 179.35(19) . . . . ?
C9 P1 C15 N4 51.7(2) . . . . ?
C10 P1 C15 N4 -56.7(2) . . . . ?
O4 P1 C15 C19 -2.2(3) . . . . ?
C9 P1 C15 C19 -129.8(2) . . . . ?
C10 P1 C15 C19 121.8(2) . . . . ?
C15 N4 C16 C17 -0.4(4) . . . . ?
Cu1 N4 C16 C17 173.5(2) . . . . ?
N4 C16 C17 C18 1.1(4) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
N4 C15 C19 C18 1.5(4) . . . . ?
P1 C15 C19 C18 -176.9(2) . . . . ?
C17 C18 C19 C15 -0.7(4) . . . . ?
Cu1 O6 C20 C21 107.1(4) . . . . ?
Cu1 O6 C20 C24 -70.5(4) . . . . ?
O6 C20 C21 C22 -8.6(5) . . . . ?
C24 C20 C21 C22 169.1(3) . . . . ?
C20 C21 C22 O5 3.8(5) . . . . ?
C20 C21 C22 C23 -172.0(3) . . . . ?
O5 C22 C23 F9 28.3(4) . . . . ?
C21 C22 C23 F9 -155.3(3) . . . . ?
O5 C22 C23 F8 -91.2(3) . . . . ?
C21 C22 C23 F8 85.2(3) . . . . ?
O5 C22 C23 F7 149.7(3) . . . . ?
C21 C22 C23 F7 -33.9(4) . . . . ?
O6 C20 C24 F10 -11.5(4) . . . . ?
C21 C20 C24 F10 170.5(3) . . . . ?
O6 C20 C24 F11 109.5(3) . . . . ?
C21 C20 C24 F11 -68.4(3) . . . . ?
O6 C20 C24 F12 -132.5(3) . . . . ?
C21 C20 C24 F12 49.6(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
C25 H14 F3 0.91(4) 2.56(4) 3.175(3) 125(3) 4_665
C16 H10 F12 0.93 2.58 3.435(4) 152.7 4_666
C14 H3 F3 0.93 2.47 3.247(4) 140.5 3_556
C11 H6 O5 0.93 2.61 3.522(4) 165.7 .
C8 H11 O6 0.93 2.36 3.283(3) 169.3 2_545
C6 H12 O4 0.93 2.42 3.210(3) 143.4 2
C16 H10 F12 0.93 2.58 3.435(4) 152.7 4_666
C14 H3 F3 0.93 2.47 3.247(4) 140.5 3_556
C11 H6 O5 0.93 2.61 3.522(4) 165.7 .
C8 H11 O6 0.93 2.36 3.283(3) 169.3 2_545
C6 H12 O4 0.93 2.42 3.210(3) 143.4 2
C16 H10 F12 0.93 2.58 3.435(4) 152.7 4_666
C14 H3 F3 0.93 2.47 3.247(4) 140.5 3_556
C11 H6 O5 0.93 2.61 3.522(4) 165.7 .
C8 H11 O6 0.93 2.36 3.283(3) 169.3 2_545
C6 H12 O4 0.93 2.42 3.210(3) 143.4 2
C16 H10 F12 0.93 2.58 3.435(4) 152.7 4_666
C14 H3 F3 0.93 2.47 3.247(4) 140.5 3_556
C11 H6 O5 0.93 2.61 3.522(4) 165.7 .
C8 H11 O6 0.93 2.36 3.283(3) 169.3 2_545
C6 H12 O4 0.93 2.42 3.210(3) 143.4 2
C16 H10 F12 0.93 2.58 3.435(4) 152.7 4_666
C14 H3 F3 0.93 2.47 3.247(4) 140.5 3_556
C11 H6 O5 0.93 2.61 3.522(4) 165.7 .
C8 H11 O6 0.93 2.36 3.283(3) 169.3 2_545
C6 H12 O4 0.93 2.42 3.210(3) 143.4 2
C16 H10 F12 0.93 2.58 3.435(4) 152.7 4_666
C14 H3 F3 0.93 2.47 3.247(4) 140.5 3_556
C11 H6 O5 0.93 2.61 3.522(4) 165.7 .
C7 H2 O5 0.93 2.64 3.319(4) 130.1 2_545
C6 H12 O4 0.93 2.42 3.210(3) 143.4 2
C6 H12 O4 0.93 2.42 3.210(3) 143.4 2
C8 H11 O6 0.93 2.36 3.283(3) 169.3 2_545
C11 H6 O5 0.93 2.61 3.522(4) 165.7 .
C14 H3 F3 0.93 2.47 3.247(4) 140.5 3_556
C16 H10 F12 0.93 2.58 3.435(4) 152.7 4_666
C6 H12 O4 0.93 2.42 3.210(3) 143.4 2
C8 H11 O6 0.93 2.36 3.283(3) 169.3 2_545
C11 H6 O5 0.93 2.61 3.522(4) 165.7 .
C14 H3 F3 0.93 2.47 3.247(4) 140.5 3_556
C16 H10 F12 0.93 2.58 3.435(4) 152.7 4_666
C6 H12 O4 0.93 2.42 3.210(3) 143.4 2
C8 H11 O6 0.93 2.36 3.283(3) 169.3 2_545
C11 H6 O5 0.93 2.61 3.522(4) 165.7 .
C14 H3 F3 0.93 2.47 3.247(4) 140.5 3_556
C16 H10 F12 0.93 2.58 3.435(4) 152.7 4_666
C6 H12 O4 0.93 2.42 3.210(3) 143.4 2
C8 H11 O6 0.93 2.36 3.283(3) 169.3 2_545
C11 H6 O5 0.93 2.61 3.522(4) 165.7 .
C14 H3 F3 0.93 2.47 3.247(4) 140.5 3_556
C16 H10 F12 0.93 2.58 3.435(4) 152.7 4_666
C25 H14 F3 0.91(4) 2.56(4) 3.175(3) 125(3) 4_665

_refine_diff_density_max         2.625
_refine_diff_density_min         -1.451
_refine_diff_density_rms         0.116

_shelxl_version_number           2013-3

