# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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 1812303'
_audit_update_record             
;
2017-12-19 deposited with the CCDC.
2018-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 Co F N2 O6 P2'
_chemical_formula_weight         448.16

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_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                   8.3161(9)
_cell_length_b                   8.5014(7)
_cell_length_c                   13.3774(12)
_cell_angle_alpha                95.080(3)
_cell_angle_beta                 105.064(4)
_cell_angle_gamma                107.257(3)
_cell_volume                     857.96(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2248
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      25.15

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    1.232
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6663
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7045
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.030
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2993
_reflns_number_gt                2215
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0206P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2993
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.0670
_refine_ls_wR_factor_gt          0.0628
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
C1 C 0.8056(5) 1.0012(4) 0.2661(2) 0.0140(8) Uani 1 1 d . . . . .
C2 C 0.9589(5) 1.1286(4) 0.3258(3) 0.0254(10) Uani 1 1 d . . . . .
H2 H 1.0488 1.1743 0.2945 0.030 Uiso 1 1 calc R U . . .
C3 C 0.9829(6) 1.1899(5) 0.4294(3) 0.0329(11) Uani 1 1 d . . . . .
H3 H 1.0877 1.2774 0.4695 0.039 Uiso 1 1 calc R U . . .
C4 C 0.8536(6) 1.1226(4) 0.4729(3) 0.0262(10) Uani 1 1 d . . . . .
C5 C 0.7006(5) 0.9969(4) 0.4179(3) 0.0263(10) Uani 1 1 d . . . . .
H5 H 0.6127 0.9515 0.4505 0.032 Uiso 1 1 calc R U . . .
C6 C 0.6767(5) 0.9373(4) 0.3135(3) 0.0202(9) Uani 1 1 d . . . . .
H6 H 0.5703 0.8513 0.2738 0.024 Uiso 1 1 calc R U . . .
C7 C 0.7791(5) 0.9415(4) 0.1509(2) 0.0140(8) Uani 1 1 d . . . . .
H7A H 0.6548 0.9240 0.1115 0.017 Uiso 1 1 calc R U . . .
H7B H 0.8543 1.0326 0.1253 0.017 Uiso 1 1 calc R U . . .
C8 C 0.7049(4) 0.6407(3) 0.1559(2) 0.0105(7) Uani 1 1 d . . . . .
H8A H 0.5856 0.6495 0.1445 0.013 Uiso 1 1 calc R U . . .
H8B H 0.7558 0.6437 0.2319 0.013 Uiso 1 1 calc R U . . .
C9 C 1.0072(4) 0.8063(4) 0.1707(2) 0.0117(8) Uani 1 1 d . . . . .
H9A H 1.0167 0.7006 0.1929 0.014 Uiso 1 1 calc R U . . .
H9B H 1.0571 0.8949 0.2342 0.014 Uiso 1 1 calc R U . . .
C10 C 0.5576(5) 0.6981(4) -0.2825(3) 0.0201(9) Uani 1 1 d . . . . .
H10 H 0.5239 0.7816 -0.2496 0.024 Uiso 1 1 calc R U . . .
C11 C 0.4896(5) 0.6489(4) -0.3900(3) 0.0245(9) Uani 1 1 d . . . . .
H11 H 0.4110 0.6983 -0.4291 0.029 Uiso 1 1 calc R U . . .
C12 C 0.5351(5) 0.5278(4) -0.4417(2) 0.0134(8) Uani 1 1 d . . . . .
C13 C 0.6505(5) 0.4623(4) -0.3783(2) 0.0173(8) Uani 1 1 d . . . . .
H13 H 0.6868 0.3789 -0.4091 0.021 Uiso 1 1 calc R U . . .
C14 C 0.7126(5) 0.5174(4) -0.2714(2) 0.0149(8) Uani 1 1 d . . . . .
H14 H 0.7912 0.4697 -0.2304 0.018 Uiso 1 1 calc R U . . .
Co1 Co 0.74868(6) 0.71973(5) -0.05474(3) 0.00857(13) Uani 1 1 d . . . . .
F1 F 0.8743(4) 1.1844(3) 0.57532(15) 0.0461(7) Uani 1 1 d . . . . .
N1 N 0.8177(4) 0.7854(3) 0.12331(19) 0.0094(6) Uani 1 1 d . . . . .
N2 N 0.6687(4) 0.6344(3) -0.22173(19) 0.0130(7) Uani 1 1 d . . . . .
O1 O 1.0206(3) 0.7547(2) -0.02583(15) 0.0101(5) Uani 1 1 d . . . . .
O2 O 1.2024(3) 1.0447(2) 0.08652(16) 0.0128(5) Uani 1 1 d . . . . .
O3 O 1.2982(3) 0.8016(2) 0.12428(16) 0.0137(5) Uani 1 1 d . . . . .
H3A H 1.2851 0.7095 0.0873 0.016 Uiso 1 1 d R U . . .
O4 O 0.7133(3) 0.4771(2) -0.02336(15) 0.0106(5) Uani 1 1 d . . . . .
O5 O 0.8463(3) 0.3939(2) 0.14702(16) 0.0139(5) Uani 1 1 d . . . . .
H5A H 0.8864 0.3462 0.1053 0.017 Uiso 1 1 d R U . . .
O6 O 0.5157(3) 0.3133(2) 0.07409(16) 0.0116(5) Uani 1 1 d . . . . .
P1 P 1.13597(12) 0.86114(9) 0.08075(6) 0.0088(2) Uani 1 1 d . . . . .
P2 P 0.68670(12) 0.44245(9) 0.08225(6) 0.0091(2) 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
C1 C6 1.383(5) . ?
C1 C2 1.391(4) . ?
C1 C7 1.516(4) . ?
C2 C3 1.378(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.357(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.367(5) . ?
C4 F1 1.370(4) . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.493(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N1 1.485(4) . ?
C8 P2 1.819(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N1 1.487(4) . ?
C9 P1 1.812(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N2 1.338(4) . ?
C10 C11 1.377(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(5) . ?
C12 C12 1.494(6) 2_664 ?
C13 C14 1.373(4) . ?
C13 H13 0.9500 . ?
C14 N2 1.338(4) . ?
C14 H14 0.9500 . ?
Co1 O2 2.028(2) 2_775 ?
Co1 O6 2.075(2) 2_665 ?
Co1 O4 2.091(2) . ?
Co1 O1 2.116(2) . ?
Co1 N2 2.148(2) . ?
Co1 N1 2.276(2) . ?
O1 P1 1.522(2) . ?
O2 P1 1.480(2) . ?
O2 Co1 2.028(2) 2_775 ?
O3 P1 1.569(2) . ?
O3 H3A 0.8500 . ?
O4 P2 1.526(2) . ?
O5 P2 1.573(2) . ?
O5 H5A 0.8501 . ?
O6 P2 1.487(2) . ?
O6 Co1 2.075(2) 2_665 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.2(3) . . ?
C6 C1 C7 121.6(3) . . ?
C2 C1 C7 120.1(3) . . ?
C3 C2 C1 121.2(4) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 118.6(4) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 122.6(3) . . ?
C3 C4 F1 119.2(3) . . ?
C5 C4 F1 118.2(4) . . ?
C4 C5 C6 118.5(4) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 120.9(3) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
N1 C7 C1 117.5(3) . . ?
N1 C7 H7A 107.9 . . ?
C1 C7 H7A 107.9 . . ?
N1 C7 H7B 107.9 . . ?
C1 C7 H7B 107.9 . . ?
H7A C7 H7B 107.2 . . ?
N1 C8 P2 111.6(2) . . ?
N1 C8 H8A 109.3 . . ?
P2 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
P2 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N1 C9 P1 112.8(2) . . ?
N1 C9 H9A 109.0 . . ?
P1 C9 H9A 109.0 . . ?
N1 C9 H9B 109.0 . . ?
P1 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
N2 C10 C11 123.4(3) . . ?
N2 C10 H10 118.3 . . ?
C11 C10 H10 118.3 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C13 115.8(3) . . ?
C11 C12 C12 122.0(4) . 2_664 ?
C13 C12 C12 122.2(4) . 2_664 ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
N2 C14 C13 123.7(3) . . ?
N2 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
O2 Co1 O6 92.54(9) 2_775 2_665 ?
O2 Co1 O4 176.41(10) 2_775 . ?
O6 Co1 O4 90.93(8) 2_665 . ?
O2 Co1 O1 88.36(9) 2_775 . ?
O6 Co1 O1 176.80(8) 2_665 . ?
O4 Co1 O1 88.23(9) . . ?
O2 Co1 N2 86.84(9) 2_775 . ?
O6 Co1 N2 85.85(10) 2_665 . ?
O4 Co1 N2 92.49(9) . . ?
O1 Co1 N2 97.27(10) . . ?
O2 Co1 N1 98.21(8) 2_775 . ?
O6 Co1 N1 91.84(9) 2_665 . ?
O4 Co1 N1 82.59(8) . . ?
O1 Co1 N1 84.99(9) . . ?
N2 Co1 N1 174.54(9) . . ?
C8 N1 C9 110.1(2) . . ?
C8 N1 C7 111.2(3) . . ?
C9 N1 C7 111.6(2) . . ?
C8 N1 Co1 105.99(16) . . ?
C9 N1 Co1 108.65(18) . . ?
C7 N1 Co1 109.06(18) . . ?
C14 N2 C10 116.2(3) . . ?
C14 N2 Co1 126.4(2) . . ?
C10 N2 Co1 117.4(2) . . ?
P1 O1 Co1 113.73(12) . . ?
P1 O2 Co1 164.87(14) . 2_775 ?
P1 O3 H3A 110.4 . . ?
P2 O4 Co1 118.16(11) . . ?
P2 O5 H5A 109.9 . . ?
P2 O6 Co1 142.33(14) . 2_665 ?
O2 P1 O1 117.28(12) . . ?
O2 P1 O3 108.29(13) . . ?
O1 P1 O3 110.10(12) . . ?
O2 P1 C9 111.16(14) . . ?
O1 P1 C9 105.66(13) . . ?
O3 P1 C9 103.49(14) . . ?
O6 P2 O4 114.42(12) . . ?
O6 P2 O5 110.86(12) . . ?
O4 P2 O5 108.89(13) . . ?
O6 P2 C8 110.16(14) . . ?
O4 P2 C8 106.77(12) . . ?
O5 P2 C8 105.27(14) . . ?

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
C6 C1 C2 C3 0.2(6) . . . . ?
C7 C1 C2 C3 177.3(4) . . . . ?
C1 C2 C3 C4 0.4(6) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
C2 C3 C4 F1 -178.8(3) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
F1 C4 C5 C6 178.1(3) . . . . ?
C4 C5 C6 C1 1.0(6) . . . . ?
C2 C1 C6 C5 -0.9(5) . . . . ?
C7 C1 C6 C5 -177.9(3) . . . . ?
C6 C1 C7 N1 -83.7(4) . . . . ?
C2 C1 C7 N1 99.3(4) . . . . ?
N2 C10 C11 C12 -0.2(6) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C10 C11 C12 C12 -179.6(4) . . . 2_664 ?
C11 C12 C13 C14 0.1(5) . . . . ?
C12 C12 C13 C14 179.7(4) 2_664 . . . ?
C12 C13 C14 N2 -0.1(5) . . . . ?
P2 C8 N1 C9 -77.4(3) . . . . ?
P2 C8 N1 C7 158.3(2) . . . . ?
P2 C8 N1 Co1 39.9(3) . . . . ?
P1 C9 N1 C8 140.1(2) . . . . ?
P1 C9 N1 C7 -95.9(3) . . . . ?
P1 C9 N1 Co1 24.4(2) . . . . ?
C1 C7 N1 C8 59.8(4) . . . . ?
C1 C7 N1 C9 -63.6(4) . . . . ?
C1 C7 N1 Co1 176.4(2) . . . . ?
C13 C14 N2 C10 0.0(5) . . . . ?
C13 C14 N2 Co1 176.8(3) . . . . ?
C11 C10 N2 C14 0.1(5) . . . . ?
C11 C10 N2 Co1 -177.0(3) . . . . ?
Co1 O2 P1 O1 6.3(7) 2_775 . . . ?
Co1 O2 P1 O3 131.5(6) 2_775 . . . ?
Co1 O2 P1 C9 -115.4(6) 2_775 . . . ?
Co1 O1 P1 O2 -88.05(16) . . . . ?
Co1 O1 P1 O3 147.58(12) . . . . ?
Co1 O1 P1 C9 36.45(16) . . . . ?
N1 C9 P1 O2 87.5(2) . . . . ?
N1 C9 P1 O1 -40.7(2) . . . . ?
N1 C9 P1 O3 -156.43(19) . . . . ?
Co1 O6 P2 O4 -82.7(2) 2_665 . . . ?
Co1 O6 P2 O5 153.64(19) 2_665 . . . ?
Co1 O6 P2 C8 37.5(2) 2_665 . . . ?
Co1 O4 P2 O6 119.57(14) . . . . ?
Co1 O4 P2 O5 -115.77(14) . . . . ?
Co1 O4 P2 C8 -2.58(19) . . . . ?
N1 C8 P2 O6 -151.7(2) . . . . ?
N1 C8 P2 O4 -26.9(3) . . . . ?
N1 C8 P2 O5 88.7(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
O5 H5A O1 0.85 1.77 2.617(3) 176.3 2_765
O3 H3A O4 0.85 1.74 2.585(3) 172.0 2_765

_refine_diff_density_max         0.394
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.092

####################################################################### 
# 
# 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_complex_2
_database_code_depnum_ccdc_archive 'CCDC 1812308'
_audit_update_record             
;
2018-06-22 deposited with the CCDC.
2018-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H14 Cu F N O7 P2'
_chemical_formula_weight         392.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_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                   14.5374(12)
_cell_length_b                   10.4704(8)
_cell_length_c                   9.1811(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.314(3)
_cell_angle_gamma                90
_cell_volume                     1379.05(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2396
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      25.35

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.891
_exptl_crystal_F_000             796
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    1.859
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6182
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6145
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.840
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2415
_reflns_number_gt                1872
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0320P)²+1.0400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2415
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0794
_refine_ls_wR_factor_gt          0.0748
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
C1 C 0.1123(3) 0.6492(4) 0.6365(5) 0.0276(11) Uani 1 1 d . . . . .
H1 H 0.0982 0.5628 0.6101 0.033 Uiso 1 1 calc R U . . .
C2 C 0.0399(3) 0.7337(5) 0.6464(6) 0.0401(13) Uani 1 1 d . . . . .
H2 H -0.0232 0.7062 0.6294 0.048 Uiso 1 1 calc R U . . .
C3 C 0.0627(3) 0.8579(5) 0.6813(6) 0.0362(12) Uani 1 1 d . . . . .
C4 C 0.1521(3) 0.9012(4) 0.7098(5) 0.0295(11) Uani 1 1 d . . . . .
H4 H 0.1653 0.9880 0.7348 0.035 Uiso 1 1 calc R U . . .
C5 C 0.2230(3) 0.8155(4) 0.7013(4) 0.0203(9) Uani 1 1 d . . . . .
H5 H 0.2860 0.8437 0.7208 0.024 Uiso 1 1 calc R U . . .
C6 C 0.2036(3) 0.6878(4) 0.6643(4) 0.0154(9) Uani 1 1 d . . . . .
C7 C 0.2808(3) 0.5932(4) 0.6518(4) 0.0133(8) Uani 1 1 d . . . . .
H7A H 0.2563 0.5282 0.5772 0.016 Uiso 1 1 calc R U . . .
H7B H 0.3318 0.6391 0.6144 0.016 Uiso 1 1 calc R U . . .
C8 C 0.2507(3) 0.4449(4) 0.8514(4) 0.0128(8) Uani 1 1 d . . . . .
H8A H 0.1899 0.4897 0.8365 0.015 Uiso 1 1 calc R U . . .
H8B H 0.2702 0.4309 0.9586 0.015 Uiso 1 1 calc R U . . .
C9 C 0.3682(3) 0.6148(3) 0.9067(4) 0.0110(8) Uani 1 1 d . . . . .
H9A H 0.3787 0.5724 1.0043 0.013 Uiso 1 1 calc R U . . .
H9B H 0.3279 0.6903 0.9126 0.013 Uiso 1 1 calc R U . . .
Cu1 Cu 0.42475(3) 0.40496(4) 0.74231(5) 0.00942(14) Uani 1 1 d . . . . .
F1 F -0.0077(2) 0.9418(3) 0.6894(4) 0.0662(10) Uani 1 1 d . . . . .
N1 N 0.3218(2) 0.5247(3) 0.7922(3) 0.0091(7) Uani 1 1 d . . . . .
O1 O 0.33221(18) 0.2719(2) 0.7036(3) 0.0114(6) Uani 1 1 d . . . . .
O2 O 0.16031(18) 0.3028(3) 0.6190(3) 0.0177(6) Uani 1 1 d . . . . .
H2A H 0.1833 0.3039 0.5396 0.027 Uiso 1 1 d R U . . .
O3 O 0.21452(19) 0.1920(2) 0.8608(3) 0.0161(6) Uani 1 1 d . . . . .
O4 O 0.47103(18) 0.7919(2) 0.7802(3) 0.0114(6) Uani 1 1 d . . . . .
O5 O 0.50825(18) 0.5506(2) 0.7729(3) 0.0106(6) Uani 1 1 d . . . . .
O6 O 0.54721(18) 0.6774(2) 1.0078(3) 0.0130(6) Uani 1 1 d . . . . .
H6A H 0.5967 0.7070 0.9825 0.016 Uiso 1 1 d R U . . .
O7 O 0.60627(18) 0.9113(2) 0.0425(3) 0.0150(6) Uani 1 1 d . . . . .
H7C H 0.6598 0.8803 0.0745 0.018 Uiso 1 1 d R U . . .
H7D H 0.5776 0.9221 0.1152 0.018 Uiso 1 1 d R U . . .
P1 P 0.23889(7) 0.29172(10) 0.75564(10) 0.0114(2) Uani 1 1 d . . . . .
P2 P 0.47908(7) 0.66466(9) 0.85727(10) 0.0091(2) 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
C1 C6 1.371(6) . ?
C1 C2 1.389(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.367(7) . ?
C2 H2 0.9500 . ?
C3 F1 1.360(5) . ?
C3 C4 1.362(7) . ?
C4 C5 1.378(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.516(5) . ?
C7 N1 1.510(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N1 1.498(4) . ?
C8 P1 1.823(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N1 1.490(4) . ?
C9 P2 1.820(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
Cu1 O1 1.930(3) . ?
Cu1 O5 1.941(3) . ?
Cu1 O4 1.960(2) 2_646 ?
Cu1 N1 2.060(3) . ?
Cu1 O6 2.423(2) 3_667 ?
O1 P1 1.524(3) . ?
O2 P1 1.558(3) . ?
O2 H2A 0.8499 . ?
O3 P1 1.503(3) . ?
O4 P2 1.504(3) . ?
O4 Cu1 1.960(2) 2_656 ?
O5 P2 1.521(3) . ?
O6 P2 1.570(3) . ?
O6 Cu1 2.423(2) 3_667 ?
O6 H6A 0.8500 . ?
O7 H7C 0.8499 . ?
O7 H7D 0.8500 . ?

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
C6 C1 C2 121.4(4) . . ?
C6 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C3 C2 C1 117.7(5) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
F1 C3 C4 118.5(4) . . ?
F1 C3 C2 118.2(5) . . ?
C4 C3 C2 123.3(4) . . ?
C3 C4 C5 118.2(4) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C4 C5 C6 120.8(4) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.6(4) . . ?
C1 C6 C7 120.0(4) . . ?
C5 C6 C7 121.4(4) . . ?
N1 C7 C6 116.2(3) . . ?
N1 C7 H7A 108.2 . . ?
C6 C7 H7A 108.2 . . ?
N1 C7 H7B 108.2 . . ?
C6 C7 H7B 108.2 . . ?
H7A C7 H7B 107.4 . . ?
N1 C8 P1 109.4(2) . . ?
N1 C8 H8A 109.8 . . ?
P1 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
P1 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
N1 C9 P2 108.9(2) . . ?
N1 C9 H9A 109.9 . . ?
P2 C9 H9A 109.9 . . ?
N1 C9 H9B 109.9 . . ?
P2 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
O1 Cu1 O5 174.32(11) . . ?
O1 Cu1 O4 94.14(11) . 2_646 ?
O5 Cu1 O4 90.79(11) . 2_646 ?
O1 Cu1 N1 88.31(11) . . ?
O5 Cu1 N1 87.11(11) . . ?
O4 Cu1 N1 173.18(11) 2_646 . ?
O1 Cu1 O6 85.55(9) . 3_667 ?
O5 Cu1 O6 97.89(9) . 3_667 ?
O4 Cu1 O6 82.54(9) 2_646 3_667 ?
N1 Cu1 O6 91.31(10) . 3_667 ?
C9 N1 C8 110.9(3) . . ?
C9 N1 C7 111.8(3) . . ?
C8 N1 C7 112.0(3) . . ?
C9 N1 Cu1 106.3(2) . . ?
C8 N1 Cu1 108.1(2) . . ?
C7 N1 Cu1 107.4(2) . . ?
P1 O1 Cu1 118.26(14) . . ?
P1 O2 H2A 110.7 . . ?
P2 O4 Cu1 125.59(16) . 2_656 ?
P2 O5 Cu1 118.12(15) . . ?
P2 O6 Cu1 142.04(14) . 3_667 ?
P2 O6 H6A 103.4 . . ?
Cu1 O6 H6A 111.6 3_667 . ?
H7C O7 H7D 108.5 . . ?
O3 P1 O1 114.90(15) . . ?
O3 P1 O2 110.53(15) . . ?
O1 P1 O2 109.38(14) . . ?
O3 P1 C8 108.34(15) . . ?
O1 P1 C8 104.60(16) . . ?
O2 P1 C8 108.79(17) . . ?
O4 P2 O5 117.55(14) . . ?
O4 P2 O6 109.20(14) . . ?
O5 P2 O6 109.09(15) . . ?
O4 P2 C9 111.50(16) . . ?
O5 P2 C9 103.47(16) . . ?
O6 P2 C9 105.25(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
C6 C1 C2 C3 1.5(8) . . . . ?
C1 C2 C3 F1 179.2(5) . . . . ?
C1 C2 C3 C4 -1.5(8) . . . . ?
F1 C3 C4 C5 -180.0(4) . . . . ?
C2 C3 C4 C5 0.7(8) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C2 C1 C6 C5 -0.8(7) . . . . ?
C2 C1 C6 C7 -179.7(4) . . . . ?
C4 C5 C6 C1 0.0(6) . . . . ?
C4 C5 C6 C7 178.9(4) . . . . ?
C1 C6 C7 N1 -92.5(4) . . . . ?
C5 C6 C7 N1 88.6(4) . . . . ?
P2 C9 N1 C8 159.1(2) . . . . ?
P2 C9 N1 C7 -75.1(3) . . . . ?
P2 C9 N1 Cu1 41.9(3) . . . . ?
P1 C8 N1 C9 -151.6(2) . . . . ?
P1 C8 N1 C7 82.7(3) . . . . ?
P1 C8 N1 Cu1 -35.4(3) . . . . ?
C6 C7 N1 C9 -63.2(4) . . . . ?
C6 C7 N1 C8 62.0(4) . . . . ?
C6 C7 N1 Cu1 -179.5(3) . . . . ?
Cu1 O1 P1 O3 -121.20(17) . . . . ?
Cu1 O1 P1 O2 113.83(17) . . . . ?
Cu1 O1 P1 C8 -2.6(2) . . . . ?
N1 C8 P1 O3 148.6(2) . . . . ?
N1 C8 P1 O1 25.6(3) . . . . ?
N1 C8 P1 O2 -91.2(3) . . . . ?
Cu1 O4 P2 O5 -79.4(2) 2_656 . . . ?
Cu1 O4 P2 O6 45.5(2) 2_656 . . . ?
Cu1 O4 P2 C9 161.37(17) 2_656 . . . ?
Cu1 O5 P2 O4 -121.65(17) . . . . ?
Cu1 O5 P2 O6 113.38(16) . . . . ?
Cu1 O5 P2 C9 1.7(2) . . . . ?
Cu1 O6 P2 O4 147.5(2) 3_667 . . . ?
Cu1 O6 P2 O5 -82.8(3) 3_667 . . . ?
Cu1 O6 P2 C9 27.7(3) 3_667 . . . ?
N1 C9 P2 O4 97.7(3) . . . . ?
N1 C9 P2 O5 -29.5(3) . . . . ?
N1 C9 P2 O6 -144.0(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
O7 H7D O5 0.85 1.91 2.764(3) 177.4 4_575
O7 H7C O3 0.85 1.98 2.828(4) 177.2 3_666
O7 H7C O1 0.85 2.57 3.039(3) 115.6 3_666
O6 H6A O1 0.85 2.24 2.987(3) 146.6 2_656
O2 H2A O3 0.85 1.77 2.617(3) 171.8 4_565

_refine_diff_density_max         0.529
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.105

_vrf_PLAT780_complex_2           
;
PROBLEM:  Coordinates do not Form a Properly Connected Set    
RESPONSE: The O atom (O7) of a weakly coordinated solvent 
water molecule is located in the special position. 
;
####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1812312'
_audit_update_record             
;
2017-12-19 deposited with the CCDC.
2018-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H31 F2 Fe3 N2 O18 P4'
_chemical_formula_weight         892.88

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

_cell_length_a                   10.5218(7)
_cell_length_b                   9.8194(6)
_cell_length_c                   28.8151(19)
_cell_angle_alpha                90
_cell_angle_beta                 91.524(3)
_cell_angle_gamma                90
_cell_volume                     2976.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3722
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      25.35

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.993
_exptl_crystal_F_000             1812
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    1.756
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5914
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12135
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_av_R_equivalents  0.0851
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.838
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2608
_reflns_number_gt                1906
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0331P)²+17.8412P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2608
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
C1 C 0.4691(4) 0.3876(5) 0.80041(18) 0.0144(11) Uani 1 1 d . . . . .
C2 C 0.3652(5) 0.4644(5) 0.7850(2) 0.0213(12) Uani 1 1 d . . . . .
H2 H 0.3312 0.5313 0.8050 0.026 Uiso 1 1 calc R U . . .
C3 C 0.3103(5) 0.4460(6) 0.7415(2) 0.0314(15) Uani 1 1 d . . . . .
H3 H 0.2384 0.4977 0.7313 0.038 Uiso 1 1 calc R U . . .
C4 C 0.3634(6) 0.3503(6) 0.7136(2) 0.0299(14) Uani 1 1 d . . . . .
C5 C 0.4670(7) 0.2735(6) 0.7267(2) 0.0377(16) Uani 1 1 d . . . . .
H5 H 0.5021 0.2089 0.7061 0.045 Uiso 1 1 calc R U . . .
C6 C 0.5192(5) 0.2929(6) 0.7709(2) 0.0278(14) Uani 1 1 d . . . . .
H6 H 0.5905 0.2401 0.7809 0.033 Uiso 1 1 calc R U . . .
C7 C 0.5331(4) 0.4151(5) 0.84677(17) 0.0133(11) Uani 1 1 d . . . . .
H7A H 0.5273 0.5139 0.8532 0.016 Uiso 1 1 calc R U . . .
H7B H 0.6244 0.3923 0.8445 0.016 Uiso 1 1 calc R U . . .
C8 C 0.5067(4) 0.1875(5) 0.88713(17) 0.0114(11) Uani 1 1 d . . . . .
H8A H 0.5945 0.1708 0.8770 0.014 Uiso 1 1 calc R U . . .
H8B H 0.4473 0.1420 0.8649 0.014 Uiso 1 1 calc R U . . .
C9 C 0.3412(4) 0.3660(5) 0.89477(17) 0.0114(10) Uani 1 1 d . . . . .
H9A H 0.3050 0.2908 0.9131 0.014 Uiso 1 1 calc R U . . .
H9B H 0.2964 0.3675 0.8641 0.014 Uiso 1 1 calc R U . . .
F1 F 0.3112(4) 0.3306(4) 0.67024(13) 0.0567(12) Uani 1 1 d . . . . .
Fe1 Fe 0.41373(6) 0.37578(7) 1.01871(3) 0.01103(19) Uani 1 1 d . . . . .
Fe2 Fe 0.2500 -0.00713(11) 1.0000 0.0165(3) Uani 1 2 d S T P . .
N1 N 0.4804(3) 0.3386(4) 0.88786(15) 0.0117(9) Uani 1 1 d . . . . .
O1 O 0.3527(3) 0.0595(3) 0.94659(13) 0.0170(8) Uani 1 1 d . . . . .
O2 O 0.5057(3) 0.2428(3) 0.97671(12) 0.0120(7) Uani 1 1 d . . . . .
O3 O 0.5892(3) 0.0111(3) 0.95295(12) 0.0133(8) Uani 1 1 d . . . . .
O4 O 0.1763(3) 0.5161(3) 0.94047(12) 0.0129(8) Uani 1 1 d . . . . .
O5 O 0.3376(3) 0.6408(3) 0.89161(12) 0.0140(8) Uani 1 1 d . . . . .
O6 O 0.4116(3) 0.5227(3) 0.96524(11) 0.0102(7) Uani 1 1 d . . . . .
O7 O 0.2500 -0.2148(5) 1.0000 0.0338(15) Uani 1 2 d S T P . .
H7D H 0.3256 -0.2453 1.0014 0.041 Uiso 0.5 1 d R U P . .
H7C H 0.2129 -0.2453 0.9756 0.041 Uiso 0.5 1 d R U P . .
O8 O 0.2500 0.2908(5) 1.0000 0.0149(11) Uani 1 2 d S T P . .
H8C H 0.2332 0.3415 0.9767 0.018 Uiso 0.5 1 d R U P . .
O9 O 0.4393(3) 0.2487(3) 1.07555(12) 0.0159(8) Uani 1 1 d . . . . .
H9C H 0.4308 0.1673 1.0671 0.024 Uiso 1 1 d R U . . .
H9D H 0.5072 0.2744 1.0895 0.024 Uiso 1 1 d R U . . .
O10 O 0.8042(4) 0.0960(4) 0.85693(16) 0.0407(12) Uani 1 1 d . . . . .
H10A H 0.7927 0.0425 0.8796 0.061 Uiso 1 1 d R U . . .
H10B H 0.8216 0.1753 0.8673 0.061 Uiso 1 1 d R U . . .
P1 P 0.48643(10) 0.11773(13) 0.94580(5) 0.0109(3) Uani 1 1 d . . . . .
P2 P 0.31348(11) 0.52555(12) 0.92422(4) 0.0091(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.376(7) . ?
C1 C2 1.391(7) . ?
C1 C7 1.504(7) . ?
C2 C3 1.378(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.366(8) . ?
C3 H3 0.9500 . ?
C4 F1 1.364(6) . ?
C4 C5 1.370(8) . ?
C5 C6 1.387(8) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.519(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N1 1.509(6) . ?
C8 P1 1.842(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N1 1.508(5) . ?
C9 P2 1.809(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
Fe1 O8 1.976(2) . ?
Fe1 O2 2.041(3) . ?
Fe1 O4 2.059(3) 2_557 ?
Fe1 O9 2.071(4) . ?
Fe1 O6 2.110(3) . ?
Fe1 O6 2.131(3) 5_667 ?
Fe2 O1 2.013(3) 2_557 ?
Fe2 O1 2.013(3) . ?
Fe2 O7 2.039(5) . ?
Fe2 O3 2.140(3) 6 ?
Fe2 O3 2.140(3) 5_657 ?
O1 P1 1.520(3) . ?
O2 P1 1.528(3) . ?
O3 P1 1.515(3) . ?
O3 Fe2 2.140(3) 5_657 ?
O4 P2 1.532(3) . ?
O4 Fe1 2.059(3) 2_557 ?
O5 P2 1.497(3) . ?
O6 P2 1.549(3) . ?
O6 Fe1 2.131(3) 5_667 ?
O7 H7D 0.8500 . ?
O7 H7C 0.8499 . ?
O8 Fe1 1.976(2) 2_557 ?
O8 H8C 0.8499 . ?
O9 H9C 0.8400 . ?
O9 H9D 0.8492 . ?
O10 H10A 0.8503 . ?
O10 H10B 0.8517 . ?

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
C6 C1 C2 118.7(5) . . ?
C6 C1 C7 120.0(5) . . ?
C2 C1 C7 121.1(5) . . ?
C3 C2 C1 121.8(5) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C4 C3 C2 117.2(5) . . ?
C4 C3 H3 121.4 . . ?
C2 C3 H3 121.4 . . ?
F1 C4 C3 118.4(6) . . ?
F1 C4 C5 118.2(6) . . ?
C3 C4 C5 123.5(5) . . ?
C4 C5 C6 118.1(6) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C1 C6 C5 120.8(5) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C1 C7 N1 116.1(4) . . ?
C1 C7 H7A 108.3 . . ?
N1 C7 H7A 108.3 . . ?
C1 C7 H7B 108.3 . . ?
N1 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
N1 C8 P1 109.1(3) . . ?
N1 C8 H8A 109.9 . . ?
P1 C8 H8A 109.9 . . ?
N1 C8 H8B 109.9 . . ?
P1 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
N1 C9 P2 112.7(3) . . ?
N1 C9 H9A 109.0 . . ?
P2 C9 H9A 109.0 . . ?
N1 C9 H9B 109.0 . . ?
P2 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
O8 Fe1 O2 89.53(12) . . ?
O8 Fe1 O4 91.58(12) . 2_557 ?
O2 Fe1 O4 177.73(14) . 2_557 ?
O8 Fe1 O9 93.17(13) . . ?
O2 Fe1 O9 91.72(13) . . ?
O4 Fe1 O9 90.20(13) 2_557 . ?
O8 Fe1 O6 95.59(12) . . ?
O2 Fe1 O6 90.02(13) . . ?
O4 Fe1 O6 87.90(13) 2_557 . ?
O9 Fe1 O6 171.08(13) . . ?
O8 Fe1 O6 175.86(13) . 5_667 ?
O2 Fe1 O6 90.47(12) . 5_667 ?
O4 Fe1 O6 88.29(12) 2_557 5_667 ?
O9 Fe1 O6 90.97(13) . 5_667 ?
O6 Fe1 O6 80.27(13) . 5_667 ?
O1 Fe2 O1 142.1(2) 2_557 . ?
O1 Fe2 O7 108.96(10) 2_557 . ?
O1 Fe2 O7 108.96(10) . . ?
O1 Fe2 O3 93.39(13) 2_557 6 ?
O1 Fe2 O3 87.30(13) . 6 ?
O7 Fe2 O3 88.94(9) . 6 ?
O1 Fe2 O3 87.30(13) 2_557 5_657 ?
O1 Fe2 O3 93.39(13) . 5_657 ?
O7 Fe2 O3 88.94(9) . 5_657 ?
O3 Fe2 O3 177.89(18) 6 5_657 ?
C9 N1 C8 110.9(4) . . ?
C9 N1 C7 113.0(4) . . ?
C8 N1 C7 113.9(4) . . ?
P1 O1 Fe2 130.5(2) . . ?
P1 O2 Fe1 143.34(18) . . ?
P1 O3 Fe2 130.4(2) . 5_657 ?
P2 O4 Fe1 131.79(19) . 2_557 ?
P2 O6 Fe1 124.29(18) . . ?
P2 O6 Fe1 135.30(19) . 5_667 ?
Fe1 O6 Fe1 99.73(13) . 5_667 ?
Fe2 O7 H7D 110.7 . . ?
Fe2 O7 H7C 110.7 . . ?
H7D O7 H7C 108.8 . . ?
Fe1 O8 Fe1 130.0(3) 2_557 . ?
Fe1 O8 H8C 51.4 2_557 . ?
Fe1 O8 H8C 97.4 . . ?
Fe1 O9 H9C 109.5 . . ?
Fe1 O9 H9D 106.6 . . ?
H9C O9 H9D 120.1 . . ?
H10A O10 H10B 109.2 . . ?
O3 P1 O1 113.32(19) . . ?
O3 P1 O2 113.15(18) . . ?
O1 P1 O2 113.73(19) . . ?
O3 P1 C8 106.4(2) . . ?
O1 P1 C8 106.5(2) . . ?
O2 P1 C8 102.7(2) . . ?
O5 P2 O4 114.45(18) . . ?
O5 P2 O6 111.85(19) . . ?
O4 P2 O6 112.34(19) . . ?
O5 P2 C9 109.2(2) . . ?
O4 P2 C9 104.85(19) . . ?
O6 P2 C9 103.28(19) . . ?

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
C6 C1 C2 C3 1.3(8) . . . . ?
C7 C1 C2 C3 176.0(5) . . . . ?
C1 C2 C3 C4 -1.1(8) . . . . ?
C2 C3 C4 F1 -179.6(5) . . . . ?
C2 C3 C4 C5 -0.1(9) . . . . ?
F1 C4 C5 C6 -179.5(6) . . . . ?
C3 C4 C5 C6 1.0(9) . . . . ?
C2 C1 C6 C5 -0.4(8) . . . . ?
C7 C1 C6 C5 -175.2(5) . . . . ?
C4 C5 C6 C1 -0.7(9) . . . . ?
C6 C1 C7 N1 -96.0(5) . . . . ?
C2 C1 C7 N1 89.3(6) . . . . ?
P2 C9 N1 C8 150.7(3) . . . . ?
P2 C9 N1 C7 -80.1(4) . . . . ?
P1 C8 N1 C9 -69.6(4) . . . . ?
P1 C8 N1 C7 161.7(3) . . . . ?
C1 C7 N1 C9 -58.2(5) . . . . ?
C1 C7 N1 C8 69.4(5) . . . . ?
Fe2 O3 P1 O1 -129.4(2) 5_657 . . . ?
Fe2 O3 P1 O2 2.0(3) 5_657 . . . ?
Fe2 O3 P1 C8 113.9(3) 5_657 . . . ?
Fe2 O1 P1 O3 74.2(3) . . . . ?
Fe2 O1 P1 O2 -56.9(3) . . . . ?
Fe2 O1 P1 C8 -169.2(3) . . . . ?
Fe1 O2 P1 O3 -135.8(3) . . . . ?
Fe1 O2 P1 O1 -4.6(4) . . . . ?
Fe1 O2 P1 C8 110.0(4) . . . . ?
N1 C8 P1 O3 -142.1(3) . . . . ?
N1 C8 P1 O1 96.8(3) . . . . ?
N1 C8 P1 O2 -23.0(3) . . . . ?
Fe1 O4 P2 O5 175.9(2) 2_557 . . . ?
Fe1 O4 P2 O6 -55.2(3) 2_557 . . . ?
Fe1 O4 P2 C9 56.3(3) 2_557 . . . ?
Fe1 O6 P2 O5 -179.24(19) . . . . ?
Fe1 O6 P2 O5 -10.7(3) 5_667 . . . ?
Fe1 O6 P2 O4 50.4(3) . . . . ?
Fe1 O6 P2 O4 -141.1(2) 5_667 . . . ?
Fe1 O6 P2 C9 -62.0(3) . . . . ?
Fe1 O6 P2 C9 106.5(3) 5_667 . . . ?
N1 C9 P2 O5 72.9(4) . . . . ?
N1 C9 P2 O4 -164.0(3) . . . . ?
N1 C9 P2 O6 -46.2(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O10 H10B O5 0.85 1.94 2.789(5) 172.5 6_665
O10 H10A O1 0.85 2.25 3.033(6) 153.2 6_655
O9 H9D O5 0.85 1.90 2.732(4) 166.4 5_667
O9 H9C O3 0.84 1.86 2.695(5) 178.6 5_657
O8 H8C O9 0.85 2.50 2.941(3) 113.2 2_557
O8 H8C O6 0.85 2.61 3.028(5) 111.4 .
O8 H8C O4 0.85 2.09 2.893(5) 158.0 .
O7 H7C O4 0.85 2.58 3.234(5) 135.0 1_545
O7 H7C O2 0.85 2.18 2.654(3) 114.9 6
O7 H7D O2 0.85 1.87 2.654(3) 152.9 5_657

_refine_diff_density_max         0.768
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.119

####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1812304'
_audit_update_record             
;
2017-12-19 deposited with the CCDC.
2018-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 F N2 Ni O6 P2'
_chemical_formula_weight         447.94

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

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

_cell_length_a                   13.1948(13)
_cell_length_b                   9.8505(10)
_cell_length_c                   13.6882(18)
_cell_angle_alpha                90
_cell_angle_beta                 112.336(3)
_cell_angle_gamma                90
_cell_volume                     1645.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1320
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      25.34

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_F_000             916
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.421
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6158
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5876
_diffrn_reflns_av_unetI/netI     0.0708
_diffrn_reflns_av_R_equivalents  0.0884
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.106
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1531
_reflns_number_gt                1149
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0364P)²+1.5636P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1531
_refine_ls_number_parameters     136
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0830
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.046
_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
C1 C 0.5129(4) 0.0000 0.2612(4) 0.0116(13) Uani 1 2 d S TU P . .
C2 C 0.5441(3) 0.1210(5) 0.3173(3) 0.0177(10) Uani 1 1 d . . . . .
H2 H 0.5271 0.2048 0.2803 0.021 Uiso 1 1 calc R U . . .
C3 C 0.5995(3) 0.1219(5) 0.4261(3) 0.0237(11) Uani 1 1 d . . . . .
H3 H 0.6193 0.2049 0.4640 0.028 Uiso 1 1 calc R U . . .
C4 C 0.6248(5) 0.0000 0.4772(5) 0.0248(17) Uani 1 2 d S T P . .
C5 C 0.4462(4) 0.0000 0.1426(4) 0.0110(13) Uani 1 2 d S T P . .
H5A H 0.4659 0.0812 0.1110 0.013 Uiso 0.5 1 d R U P . .
H5B H 0.4659 -0.0812 0.1110 0.013 Uiso 0.5 1 d R U P . .
C6 C 0.2939(3) 0.1266(4) 0.1580(3) 0.0112(9) Uani 1 1 d . . . . .
H6A H 0.3520 0.1947 0.1674 0.013 Uiso 1 1 calc R U . . .
H6B H 0.2941 0.1062 0.2289 0.013 Uiso 1 1 calc R U . . .
C7 C 0.1939(5) 0.0000 -0.2850(5) 0.0259(16) Uani 1 2 d S TU P . .
H7 H 0.2717 0.0000 -0.2546 0.031 Uiso 1 2 calc R U P . .
C8 C 0.1428(5) 0.0000 -0.3935(5) 0.0287(17) Uani 1 2 d S TU P . .
H8 H 0.1859 0.0000 -0.4356 0.034 Uiso 1 2 calc R U P . .
C9 C 0.0287(4) 0.0000 -0.4423(4) 0.0139(13) Uani 1 2 d S T P . .
C10 C -0.0272(4) 0.0000 -0.3739(4) 0.0128(13) Uani 1 2 d S T P . .
H10 H -0.1051 0.0000 -0.4020 0.015 Uiso 1 2 calc R U P . .
C11 C 0.0290(4) 0.0000 -0.2665(4) 0.0086(12) Uani 1 2 d S T P . .
H11 H -0.0118 0.0000 -0.2223 0.010 Uiso 1 2 calc R U P . .
F1 F 0.6805(3) 0.0000 0.5844(3) 0.0420(12) Uani 1 2 d S T P . .
N1 N 0.3235(3) 0.0000 0.1152(3) 0.0080(10) Uani 1 2 d S T P . .
N2 N 0.1390(4) 0.0000 -0.2206(4) 0.0120(11) Uani 1 2 d S T P . .
Ni1 Ni 0.23046(6) 0.0000 -0.05761(5) 0.0074(2) Uani 1 2 d S T P . .
O1 O 0.1260(2) 0.1430(3) -0.0310(2) 0.0121(6) Uani 1 1 d . . . . .
O2 O 0.0847(2) 0.1571(3) 0.1360(2) 0.0136(7) Uani 1 1 d . . . . .
H2A H 0.0181 0.1566 0.0935 0.020 Uiso 1 1 d R U . . .
O3 O 0.1730(2) 0.3542(3) 0.0838(2) 0.0125(6) Uani 1 1 d . . . . .
P1 P 0.16293(8) 0.20336(11) 0.07959(8) 0.0085(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.393(5) 6 ?
C1 C2 1.393(5) . ?
C1 C5 1.524(7) . ?
C2 C3 1.387(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.366(5) . ?
C3 H3 0.9500 . ?
C4 C3 1.366(5) 6 ?
C4 F1 1.369(7) . ?
C5 N1 1.516(6) . ?
C5 H5A 0.9901 . ?
C5 H5B 0.9901 . ?
C6 N1 1.492(5) . ?
C6 P1 1.816(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.336(7) . ?
C7 C8 1.378(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.397(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(8) . ?
C9 C9 1.469(10) 5_554 ?
C10 C11 1.372(8) . ?
C10 H10 0.9500 . ?
C11 N2 1.345(7) . ?
C11 H11 0.9500 . ?
N1 C6 1.492(5) 6 ?
N1 Ni1 2.213(4) . ?
N2 Ni1 2.095(5) . ?
Ni1 O3 2.040(3) 7 ?
Ni1 O3 2.040(3) 4_545 ?
Ni1 O1 2.098(3) 6 ?
Ni1 O1 2.098(3) . ?
O1 P1 1.523(3) . ?
O2 P1 1.574(3) . ?
O2 H2A 0.8500 . ?
O3 P1 1.490(3) . ?
O3 Ni1 2.040(3) 7 ?

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
C2 C1 C2 117.7(5) 6 . ?
C2 C1 C5 121.2(3) 6 . ?
C2 C1 C5 121.2(3) . . ?
C3 C2 C1 121.5(4) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C4 C3 C2 118.1(5) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C3 123.1(6) 6 . ?
C3 C4 F1 118.4(3) 6 . ?
C3 C4 F1 118.4(3) . . ?
N1 C5 C1 113.2(4) . . ?
N1 C5 H5A 109.0 . . ?
C1 C5 H5A 108.9 . . ?
N1 C5 H5B 109.0 . . ?
C1 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
N1 C6 P1 116.7(3) . . ?
N1 C6 H6A 108.1 . . ?
P1 C6 H6A 108.1 . . ?
N1 C6 H6B 108.1 . . ?
P1 C6 H6B 108.1 . . ?
H6A C6 H6B 107.3 . . ?
N2 C7 C8 123.1(6) . . ?
N2 C7 H7 118.5 . . ?
C8 C7 H7 118.5 . . ?
C7 C8 C9 120.8(6) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 115.3(5) . . ?
C10 C9 C9 122.2(6) . 5_554 ?
C8 C9 C9 122.4(7) . 5_554 ?
C11 C10 C9 120.7(5) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
N2 C11 C10 123.2(5) . . ?
N2 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
C6 N1 C6 113.4(4) . 6 ?
C6 N1 C5 108.5(3) . . ?
C6 N1 C5 108.5(2) 6 . ?
C6 N1 Ni1 107.3(2) . . ?
C6 N1 Ni1 107.3(2) 6 . ?
C5 N1 Ni1 111.8(3) . . ?
C7 N2 C11 116.8(5) . . ?
C7 N2 Ni1 117.8(4) . . ?
C11 N2 Ni1 125.4(4) . . ?
O3 Ni1 O3 89.55(16) 7 4_545 ?
O3 Ni1 N2 87.59(12) 7 . ?
O3 Ni1 N2 87.59(12) 4_545 . ?
O3 Ni1 O1 177.35(11) 7 6 ?
O3 Ni1 O1 93.05(11) 4_545 6 ?
N2 Ni1 O1 92.00(12) . 6 ?
O3 Ni1 O1 93.05(11) 7 . ?
O3 Ni1 O1 177.35(11) 4_545 . ?
N2 Ni1 O1 92.00(12) . . ?
O1 Ni1 O1 84.35(16) 6 . ?
O3 Ni1 N1 93.33(11) 7 . ?
O3 Ni1 N1 93.33(11) 4_545 . ?
N2 Ni1 N1 178.71(18) . . ?
O1 Ni1 N1 87.05(11) 6 . ?
O1 Ni1 N1 87.04(11) . . ?
P1 O1 Ni1 116.84(14) . . ?
P1 O2 H2A 111.4 . . ?
P1 O3 Ni1 138.39(17) . 7 ?
O3 P1 O1 114.70(16) . . ?
O3 P1 O2 109.60(16) . . ?
O1 P1 O2 110.62(15) . . ?
O3 P1 C6 109.93(17) . . ?
O1 P1 C6 107.34(17) . . ?
O2 P1 C6 104.10(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
C2 C1 C2 C3 -3.2(8) 6 . . . ?
C5 C1 C2 C3 176.3(5) . . . . ?
C1 C2 C3 C4 1.2(7) . . . . ?
C2 C3 C4 C3 1.0(10) . . . 6 ?
C2 C3 C4 F1 179.3(5) . . . . ?
C2 C1 C5 N1 89.7(5) 6 . . . ?
C2 C1 C5 N1 -89.7(5) . . . . ?
N2 C7 C8 C9 0.000(1) . . . . ?
C7 C8 C9 C10 0.000(1) . . . . ?
C7 C8 C9 C9 180.000(1) . . . 5_554 ?
C8 C9 C10 C11 0.000(1) . . . . ?
C9 C9 C10 C11 180.000(1) 5_554 . . . ?
C9 C10 C11 N2 0.000(1) . . . . ?
P1 C6 N1 C6 -94.8(4) . . . 6 ?
P1 C6 N1 C5 144.5(3) . . . . ?
P1 C6 N1 Ni1 23.6(4) . . . . ?
C1 C5 N1 C6 61.8(3) . . . . ?
C1 C5 N1 C6 -61.8(3) . . . 6 ?
C1 C5 N1 Ni1 180.000(0) . . . . ?
C8 C7 N2 C11 0.000(1) . . . . ?
C8 C7 N2 Ni1 180.000(1) . . . . ?
C10 C11 N2 C7 0.000(1) . . . . ?
C10 C11 N2 Ni1 180.000(1) . . . . ?
Ni1 O3 P1 O1 -68.0(3) 7 . . . ?
Ni1 O3 P1 O2 166.9(2) 7 . . . ?
Ni1 O3 P1 C6 53.1(3) 7 . . . ?
Ni1 O1 P1 O3 122.21(18) . . . . ?
Ni1 O1 P1 O2 -113.21(17) . . . . ?
Ni1 O1 P1 C6 -0.2(2) . . . . ?
N1 C6 P1 O3 -142.1(3) . . . . ?
N1 C6 P1 O1 -16.7(4) . . . . ?
N1 C6 P1 O2 100.6(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
O2 H2A O1 0.85 1.77 2.603(3) 166.7 2

_refine_diff_density_max         0.523
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.107

####################################################################### 
# 
# 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_complex_4
_database_code_depnum_ccdc_archive 'CCDC 1812305'
_audit_update_record             
;
2018-06-22 deposited with the CCDC.
2018-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H32 Cu2 F N4 O11 P2'
_chemical_formula_weight         760.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_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                   5.9865(4)
_cell_length_b                   23.4129(12)
_cell_length_c                   21.7231(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.934(3)
_cell_angle_gamma                90
_cell_volume                     3043.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4023
_cell_measurement_theta_min      3.5148
_cell_measurement_theta_max      25.3277

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_F_000             1556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    1.573
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5197
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16037
_diffrn_reflns_av_unetI/netI     0.0799
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.215
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5300
_reflns_number_gt                3902
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0330P)²+15.1607P] 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_number_reflns         5300
_refine_ls_number_parameters     400
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0957
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.1250
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
C1 C 0.2378(12) 0.1419(3) 0.1926(3) 0.0311(16) Uani 1 1 d . . . . .
C2 C 0.2383(12) 0.1185(3) 0.2521(4) 0.0396(19) Uani 1 1 d . . . . .
H2 H 0.2373 0.1425 0.2874 0.047 Uiso 1 1 calc R U . . .
C3 C 0.2401(14) 0.0588(3) 0.2583(4) 0.049(2) Uani 1 1 d . . . . .
H3 H 0.2442 0.0418 0.2980 0.058 Uiso 1 1 calc R U . . .
C4 C 0.2361(17) 0.0251(4) 0.2065(5) 0.063(3) Uani 1 1 d . . . . .
C5 C 0.2274(17) 0.0481(4) 0.1473(5) 0.067(3) Uani 1 1 d . . . . .
H5 H 0.2216 0.0236 0.1124 0.080 Uiso 1 1 calc R U . . .
C6 C 0.2273(13) 0.1063(3) 0.1393(4) 0.045(2) Uani 1 1 d . . . . .
H6 H 0.2204 0.1225 0.0992 0.054 Uiso 1 1 calc R U . . .
C7 C 0.2548(11) 0.2062(3) 0.1850(3) 0.0263(15) Uani 1 1 d . . . . .
H7A H 0.1788 0.2171 0.1456 0.032 Uiso 1 1 calc R U . . .
H7B H 0.1740 0.2248 0.2186 0.032 Uiso 1 1 calc R U . . .
C8 C 0.6200(9) 0.2050(2) 0.1345(2) 0.0124(12) Uani 1 1 d . . . . .
H8A H 0.6031 0.1630 0.1331 0.015 Uiso 1 1 calc R U . . .
H8B H 0.7806 0.2140 0.1410 0.015 Uiso 1 1 calc R U . . .
C9 C 0.6078(9) 0.2226(2) 0.2471(2) 0.0135(12) Uani 1 1 d . . . . .
H9A H 0.7700 0.2294 0.2432 0.016 Uiso 1 1 calc R U . . .
H9B H 0.5869 0.1834 0.2629 0.016 Uiso 1 1 calc R U . . .
C10 C 0.5227(11) 0.4208(3) 0.1032(3) 0.0223(14) Uani 1 1 d . . . . .
H10 H 0.6051 0.3964 0.0775 0.027 Uiso 1 1 calc R U . . .
C11 C 0.5099(11) 0.4781(3) 0.0885(3) 0.0239(15) Uani 1 1 d . . . . .
H11 H 0.5866 0.4926 0.0542 0.029 Uiso 1 1 calc R U . . .
C12 C 0.3839(10) 0.5145(2) 0.1242(3) 0.0180(13) Uani 1 1 d . . . . .
C13 C 0.2831(12) 0.4904(3) 0.1752(3) 0.0283(16) Uani 1 1 d . . . . .
H13 H 0.1979 0.5137 0.2015 0.034 Uiso 1 1 calc R U . . .
C14 C 0.3076(11) 0.4329(3) 0.1873(3) 0.0253(15) Uani 1 1 d . . . . .
H14 H 0.2383 0.4174 0.2222 0.030 Uiso 1 1 calc R U . . .
C15 C 0.1594(10) 0.6645(2) 0.1155(3) 0.0175(13) Uani 1 1 d . . . . .
H15 H 0.0330 0.6851 0.1289 0.021 Uiso 1 1 calc R U . . .
C16 C 0.1768(11) 0.6073(3) 0.1290(3) 0.0225(14) Uani 1 1 d . . . . .
H16 H 0.0617 0.5888 0.1505 0.027 Uiso 1 1 calc R U . . .
C17 C 0.3628(10) 0.5761(2) 0.1111(3) 0.0182(13) Uani 1 1 d . . . . .
C18 C 0.5217(11) 0.6059(3) 0.0785(3) 0.0214(14) Uani 1 1 d . . . . .
H18 H 0.6502 0.5865 0.0648 0.026 Uiso 1 1 calc R U . . .
C19 C 0.4947(11) 0.6632(3) 0.0660(3) 0.0202(14) Uani 1 1 d . . . . .
H19 H 0.6063 0.6824 0.0439 0.024 Uiso 1 1 calc R U . . .
C20 C 0.7705(13) 0.1117(3) -0.0045(3) 0.0342(18) Uani 1 1 d . . . . .
H20 H 0.8948 0.1307 0.0146 0.041 Uiso 1 1 calc R U . . .
C21 C 0.7162(12) 0.0579(3) 0.0157(3) 0.0348(18) Uani 1 1 d . . . . .
H21 H 0.8042 0.0403 0.0476 0.042 Uiso 1 1 calc R U . . .
C22 C 0.5331(12) 0.0291(2) -0.0103(3) 0.0235(15) Uani 1 1 d . . . . .
C23 C 0.4178(13) 0.0571(3) -0.0574(4) 0.039(2) Uani 1 1 d . . . . .
H23 H 0.2922 0.0394 -0.0772 0.047 Uiso 1 1 calc R U . . .
C24 C 0.4841(12) 0.1108(3) -0.0758(3) 0.0335(18) Uani 1 1 d . . . . .
H24 H 0.4025 0.1289 -0.1086 0.040 Uiso 1 1 calc R U . . .
Cu1 Cu 0.47190(12) 0.31487(3) 0.16974(3) 0.01349(18) Uani 1 1 d . . . . .
Cu2 Cu 0.71537(11) 0.22243(3) -0.06746(3) 0.01027(17) Uani 1 1 d . . . . .
F1 F 0.2355(13) -0.0323(2) 0.2133(4) 0.105(2) Uani 1 1 d . . . . .
H9D H 0.01(2) 0.458(5) 0.037(3) 0.127 Uiso 1 1 d D U . . .
N1 N 0.4912(8) 0.22873(19) 0.1856(2) 0.0125(10) Uani 1 1 d . . . . .
N2 N 0.4247(8) 0.3981(2) 0.1518(2) 0.0184(11) Uani 1 1 d . . . . .
N3 N 0.3170(8) 0.69263(19) 0.0839(2) 0.0125(10) Uani 1 1 d . . . . .
N4 N 0.6570(9) 0.1383(2) -0.0496(2) 0.0172(11) Uani 1 1 d . . . . .
O1 O 0.7199(6) 0.23902(16) 0.02070(16) 0.0128(9) Uani 1 1 d . . . . .
O2 O 0.4463(7) 0.29702(16) 0.08230(18) 0.0173(9) Uani 1 1 d . . . . .
O3 O 0.3244(7) 0.20230(18) 0.03475(18) 0.0199(10) Uani 1 1 d . . . . .
O4 O 0.4311(7) 0.32422(17) 0.25739(18) 0.0215(10) Uani 1 1 d . . . . .
O5 O 0.2930(7) 0.24963(19) 0.33176(19) 0.0249(10) Uani 1 1 d . . . . .
O6 O 0.6824(7) 0.29168(16) 0.34473(17) 0.0153(9) Uani 1 1 d . . . . .
O7 O 1.0768(7) 0.2169(2) -0.06827(18) 0.0267(11) Uani 1 1 d . . . . .
H7D H 1.1394 0.2234 -0.0333 0.032 Uiso 1 1 d R U . . .
H7C H 1.1320 0.2382 -0.0956 0.032 Uiso 1 1 d R U . . .
O8 O 0.8481(7) 0.32294(19) 0.1731(2) 0.0298(11) Uani 1 1 d . . . . .
H8D H 0.9089 0.3038 0.1449 0.036 Uiso 1 1 d R U . . .
H8C H 0.9049 0.3136 0.2080 0.036 Uiso 1 1 d R U . . .
O9 O 0.0095(11) 0.4399(3) 0.0031(3) 0.0570(16) Uani 1 1 d D . . . .
H9C H 0.0169 0.4087 0.0229 0.068 Uiso 1 1 d R U . . .
O10 O 0.9962(7) 0.3605(2) 0.2870(2) 0.0351(12) Uani 1 1 d . . . . .
H10A H 1.1218 0.3452 0.2803 0.042 Uiso 1 1 d R U . . .
H10B H 0.9144 0.3361 0.3045 0.042 Uiso 1 1 d R U . . .
O11 O 0.0121(7) 0.32967(19) 0.0536(2) 0.0289(11) Uani 1 1 d . . . . .
H11A H -0.0699 0.3012 0.0440 0.035 Uiso 1 1 d R U . . .
H11B H 0.1436 0.3177 0.0621 0.035 Uiso 1 1 d R U . . .
P1 P 0.5161(3) 0.23616(6) 0.06187(7) 0.0132(3) Uani 1 1 d . . . . .
P2 P 0.4918(3) 0.27443(7) 0.30027(7) 0.0150(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.403(10) . ?
C1 C6 1.427(10) . ?
C1 C7 1.517(9) . ?
C2 C3 1.406(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.372(13) . ?
C3 H3 0.9500 . ?
C4 F1 1.353(9) . ?
C4 C5 1.395(14) . ?
C5 C6 1.373(11) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.510(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N1 1.482(7) . ?
C8 P1 1.828(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N1 1.492(7) . ?
C9 P2 1.829(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N2 1.336(8) . ?
C10 C11 1.380(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.397(8) . ?
C12 C17 1.475(8) . ?
C13 C14 1.378(8) . ?
C13 H13 0.9500 . ?
C14 N2 1.336(8) . ?
C14 H14 0.9500 . ?
C15 N3 1.356(7) . ?
C15 C16 1.375(8) . ?
C15 H15 0.9500 . ?
C16 C17 1.397(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(8) . ?
C18 C19 1.376(8) . ?
C18 H18 0.9500 . ?
C19 N3 1.336(8) . ?
C19 H19 0.9500 . ?
C20 N4 1.328(8) . ?
C20 C21 1.378(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.391(9) . ?
C21 H21 0.9500 . ?
C22 C23 1.379(9) . ?
C22 C22 1.492(12) 3_655 ?
C23 C24 1.381(9) . ?
C23 H23 0.9500 . ?
C24 N4 1.330(8) . ?
C24 H24 0.9500 . ?
Cu1 O4 1.940(4) . ?
Cu1 O2 1.946(4) . ?
Cu1 N2 2.006(5) . ?
Cu1 N1 2.049(5) . ?
Cu1 O8 2.259(4) . ?
Cu2 O6 1.939(4) 4_565 ?
Cu2 O1 1.953(4) . ?
Cu2 N3 2.028(4) 3_665 ?
Cu2 N4 2.040(5) . ?
Cu2 O7 2.168(4) . ?
N3 Cu2 2.028(4) 3_665 ?
O1 P1 1.538(4) . ?
O2 P1 1.554(4) . ?
O3 P1 1.499(4) . ?
O4 P2 1.528(4) . ?
O5 P2 1.509(4) . ?
O6 P2 1.524(4) . ?
O6 Cu2 1.939(4) 4_566 ?
O7 H7D 0.8496 . ?
O7 H7C 0.8498 . ?
O8 H8D 0.8501 . ?
O8 H8C 0.8499 . ?
O9 H9D 0.851(10) . ?
O9 H9C 0.8498 . ?
O10 H10A 0.8500 . ?
O10 H10B 0.8498 . ?
O11 H11A 0.8499 . ?
O11 H11B 0.8500 . ?

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
C2 C1 C6 121.2(7) . . ?
C2 C1 C7 119.3(6) . . ?
C6 C1 C7 119.5(6) . . ?
C1 C2 C3 118.4(8) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 119.6(8) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
F1 C4 C3 118.8(9) . . ?
F1 C4 C5 119.0(9) . . ?
C3 C4 C5 122.2(8) . . ?
C6 C5 C4 120.0(9) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 118.6(8) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
N1 C7 C1 114.3(5) . . ?
N1 C7 H7A 108.7 . . ?
C1 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
C1 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N1 C8 P1 109.1(4) . . ?
N1 C8 H8A 109.9 . . ?
P1 C8 H8A 109.9 . . ?
N1 C8 H8B 109.9 . . ?
P1 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
N1 C9 P2 108.9(4) . . ?
N1 C9 H9A 109.9 . . ?
P2 C9 H9A 109.9 . . ?
N1 C9 H9B 109.9 . . ?
P2 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
N2 C10 C11 123.2(6) . . ?
N2 C10 H10 118.4 . . ?
C11 C10 H10 118.4 . . ?
C10 C11 C12 119.5(6) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 116.9(5) . . ?
C11 C12 C17 122.4(5) . . ?
C13 C12 C17 120.7(5) . . ?
C14 C13 C12 119.9(6) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
N2 C14 C13 122.7(6) . . ?
N2 C14 H14 118.6 . . ?
C13 C14 H14 118.6 . . ?
N3 C15 C16 122.1(6) . . ?
N3 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
C15 C16 C17 120.4(6) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 116.3(6) . . ?
C18 C17 C12 122.2(5) . . ?
C16 C17 C12 121.4(5) . . ?
C19 C18 C17 120.7(6) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
N3 C19 C18 122.3(6) . . ?
N3 C19 H19 118.8 . . ?
C18 C19 H19 118.8 . . ?
N4 C20 C21 123.0(7) . . ?
N4 C20 H20 118.5 . . ?
C21 C20 H20 118.5 . . ?
C20 C21 C22 120.3(6) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C23 C22 C21 116.0(6) . . ?
C23 C22 C22 121.7(8) . 3_655 ?
C21 C22 C22 122.2(7) . 3_655 ?
C22 C23 C24 120.4(7) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
N4 C24 C23 123.0(6) . . ?
N4 C24 H24 118.5 . . ?
C23 C24 H24 118.5 . . ?
O4 Cu1 O2 166.86(18) . . ?
O4 Cu1 N2 93.40(18) . . ?
O2 Cu1 N2 90.76(18) . . ?
O4 Cu1 N1 87.35(18) . . ?
O2 Cu1 N1 87.44(17) . . ?
N2 Cu1 N1 174.9(2) . . ?
O4 Cu1 O8 96.75(17) . . ?
O2 Cu1 O8 95.44(17) . . ?
N2 Cu1 O8 93.37(19) . . ?
N1 Cu1 O8 91.51(18) . . ?
O6 Cu2 O1 174.69(17) 4_565 . ?
O6 Cu2 N3 89.33(17) 4_565 3_665 ?
O1 Cu2 N3 88.58(17) . 3_665 ?
O6 Cu2 N4 90.58(17) 4_565 . ?
O1 Cu2 N4 90.14(17) . . ?
N3 Cu2 N4 164.6(2) 3_665 . ?
O6 Cu2 O7 92.89(16) 4_565 . ?
O1 Cu2 O7 92.24(15) . . ?
N3 Cu2 O7 98.41(18) 3_665 . ?
N4 Cu2 O7 96.98(19) . . ?
C8 N1 C9 113.3(4) . . ?
C8 N1 C7 111.9(4) . . ?
C9 N1 C7 112.6(4) . . ?
C8 N1 Cu1 105.7(3) . . ?
C9 N1 Cu1 105.5(3) . . ?
C7 N1 Cu1 107.1(3) . . ?
C14 N2 C10 117.8(5) . . ?
C14 N2 Cu1 123.6(4) . . ?
C10 N2 Cu1 118.5(4) . . ?
C19 N3 C15 118.1(5) . . ?
C19 N3 Cu2 121.8(4) . 3_665 ?
C15 N3 Cu2 120.1(4) . 3_665 ?
C20 N4 C24 117.4(5) . . ?
C20 N4 Cu2 120.4(4) . . ?
C24 N4 Cu2 121.5(4) . . ?
P1 O1 Cu2 125.2(2) . . ?
P1 O2 Cu1 117.6(2) . . ?
P2 O4 Cu1 118.5(2) . . ?
P2 O6 Cu2 128.9(2) . 4_566 ?
Cu2 O7 H7D 113.1 . . ?
Cu2 O7 H7C 112.4 . . ?
H7D O7 H7C 110.4 . . ?
Cu1 O8 H8D 112.6 . . ?
Cu1 O8 H8C 112.1 . . ?
H8D O8 H8C 109.9 . . ?
H9D O9 H9C 89.8 . . ?
H10A O10 H10B 108.7 . . ?
H11A O11 H11B 108.5 . . ?
O3 P1 O1 114.0(2) . . ?
O3 P1 O2 112.8(2) . . ?
O1 P1 O2 110.6(2) . . ?
O3 P1 C8 111.2(3) . . ?
O1 P1 C8 105.4(2) . . ?
O2 P1 C8 101.9(2) . . ?
O5 P2 O6 113.6(2) . . ?
O5 P2 O4 113.3(3) . . ?
O6 P2 O4 110.0(2) . . ?
O5 P2 C9 110.7(3) . . ?
O6 P2 C9 106.5(2) . . ?
O4 P2 C9 102.0(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
C6 C1 C2 C3 3.3(11) . . . . ?
C7 C1 C2 C3 -175.1(7) . . . . ?
C1 C2 C3 C4 -1.5(12) . . . . ?
C2 C3 C4 F1 -179.3(8) . . . . ?
C2 C3 C4 C5 -0.8(15) . . . . ?
F1 C4 C5 C6 179.9(9) . . . . ?
C3 C4 C5 C6 1.3(16) . . . . ?
C4 C5 C6 C1 0.4(14) . . . . ?
C2 C1 C6 C5 -2.8(12) . . . . ?
C7 C1 C6 C5 175.6(7) . . . . ?
C2 C1 C7 N1 86.7(8) . . . . ?
C6 C1 C7 N1 -91.8(8) . . . . ?
N2 C10 C11 C12 -2.2(10) . . . . ?
C10 C11 C12 C13 2.4(10) . . . . ?
C10 C11 C12 C17 -179.9(6) . . . . ?
C11 C12 C13 C14 -1.3(10) . . . . ?
C17 C12 C13 C14 -179.0(6) . . . . ?
C12 C13 C14 N2 -0.2(11) . . . . ?
N3 C15 C16 C17 1.3(9) . . . . ?
C15 C16 C17 C18 -1.4(9) . . . . ?
C15 C16 C17 C12 -179.1(6) . . . . ?
C11 C12 C17 C18 -23.7(9) . . . . ?
C13 C12 C17 C18 153.9(6) . . . . ?
C11 C12 C17 C16 153.9(6) . . . . ?
C13 C12 C17 C16 -28.5(9) . . . . ?
C16 C17 C18 C19 1.0(9) . . . . ?
C12 C17 C18 C19 178.7(6) . . . . ?
C17 C18 C19 N3 -0.4(10) . . . . ?
N4 C20 C21 C22 -1.2(12) . . . . ?
C20 C21 C22 C23 1.5(11) . . . . ?
C20 C21 C22 C22 -179.6(8) . . . 3_655 ?
C21 C22 C23 C24 -0.7(11) . . . . ?
C22 C22 C23 C24 -179.6(8) 3_655 . . . ?
C22 C23 C24 N4 -0.7(12) . . . . ?
P1 C8 N1 C9 -160.1(4) . . . . ?
P1 C8 N1 C7 71.2(5) . . . . ?
P1 C8 N1 Cu1 -45.1(4) . . . . ?
P2 C9 N1 C8 159.3(4) . . . . ?
P2 C9 N1 C7 -72.5(5) . . . . ?
P2 C9 N1 Cu1 44.1(4) . . . . ?
C1 C7 N1 C8 61.4(6) . . . . ?
C1 C7 N1 C9 -67.6(7) . . . . ?
C1 C7 N1 Cu1 176.8(4) . . . . ?
C13 C14 N2 C10 0.6(10) . . . . ?
C13 C14 N2 Cu1 177.9(5) . . . . ?
C11 C10 N2 C14 0.6(10) . . . . ?
C11 C10 N2 Cu1 -176.8(5) . . . . ?
C18 C19 N3 C15 0.2(9) . . . . ?
C18 C19 N3 Cu2 178.0(5) . . . 3_665 ?
C16 C15 N3 C19 -0.6(9) . . . . ?
C16 C15 N3 Cu2 -178.5(5) . . . 3_665 ?
C21 C20 N4 C24 -0.2(11) . . . . ?
C21 C20 N4 Cu2 170.0(6) . . . . ?
C23 C24 N4 C20 1.1(11) . . . . ?
C23 C24 N4 Cu2 -169.0(6) . . . . ?
Cu2 O1 P1 O3 18.1(4) . . . . ?
Cu2 O1 P1 O2 -110.2(3) . . . . ?
Cu2 O1 P1 C8 140.3(3) . . . . ?
Cu1 O2 P1 O3 115.5(3) . . . . ?
Cu1 O2 P1 O1 -115.5(3) . . . . ?
Cu1 O2 P1 C8 -3.8(3) . . . . ?
N1 C8 P1 O3 -87.7(4) . . . . ?
N1 C8 P1 O1 148.4(4) . . . . ?
N1 C8 P1 O2 32.8(4) . . . . ?
Cu2 O6 P2 O5 8.2(4) 4_566 . . . ?
Cu2 O6 P2 O4 136.3(3) 4_566 . . . ?
Cu2 O6 P2 C9 -113.8(3) 4_566 . . . ?
Cu1 O4 P2 O5 -114.9(3) . . . . ?
Cu1 O4 P2 O6 116.8(3) . . . . ?
Cu1 O4 P2 C9 4.1(3) . . . . ?
N1 C9 P2 O5 88.4(4) . . . . ?
N1 C9 P2 O6 -147.7(3) . . . . ?
N1 C9 P2 O4 -32.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O11 H11B O2 0.85 1.91 2.761(6) 175.4 .
O11 H11A O1 0.85 1.98 2.827(6) 175.6 1_455
O10 H10B O6 0.85 1.96 2.803(6) 168.9 .
O10 H10A O4 0.85 2.00 2.833(6) 168.7 1_655
O9 H9C O11 0.85 1.97 2.805(7) 168.8 .
O8 H8C O10 0.85 2.09 2.746(7) 133.1 .
O8 H8D O11 0.85 2.18 2.810(6) 130.5 1_655
O7 H7C O5 0.85 1.90 2.682(6) 152.6 4_665
O7 H7D O3 0.85 1.88 2.664(5) 152.2 1_655

_refine_diff_density_max         0.793
_refine_diff_density_min         -0.740
_refine_diff_density_rms         0.116

# start Validation Reply Form
_vrf_PLAT420_4                   
;
PROBLEM:  D-H Without Acceptor       o9     --  h9d    ...     Please Check
RESPONSE: no suitable H bonds for O9-H9D were found.                                             
;
####################################################################### 
# 
# 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_complex_1
_database_code_depnum_ccdc_archive 'CCDC 1835239'
_audit_update_record             
;
2018-06-22 deposited with the CCDC.
2018-07-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H34 Co3 F2 N2 O18 P4'
_chemical_formula_weight         905.14

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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_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                   12.7521(13)
_cell_length_b                   12.5160(11)
_cell_length_c                   9.5143(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.796(4)
_cell_angle_gamma                90
_cell_volume                     1516.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.982
_exptl_crystal_F_000             918
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.929
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(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            8653
_diffrn_reflns_av_unetI/netI     0.0928
_diffrn_reflns_av_R_equivalents  0.0985
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.077
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2671
_reflns_number_gt                1853
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0306P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2671
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
C1 C 0.6611(4) 0.0746(4) 0.9572(5) 0.0113(11) Uani 1 1 d . . . . .
H1A H 0.6492 0.1111 1.0473 0.014 Uiso 1 1 calc R U . . .
H1B H 0.6739 -0.0019 0.9784 0.014 Uiso 1 1 calc R U . . .
C2 C 0.5619(4) 0.0836(4) 0.8637(5) 0.0132(11) Uani 1 1 d . . . . .
C3 C 0.5330(4) 0.0013(4) 0.7723(6) 0.0217(13) Uani 1 1 d . . . . .
H3 H 0.5737 -0.0623 0.7725 0.026 Uiso 1 1 calc R U . . .
C4 C 0.4455(4) 0.0107(5) 0.6806(6) 0.0302(15) Uani 1 1 d . . . . .
H4 H 0.4257 -0.0457 0.6180 0.036 Uiso 1 1 calc R U . . .
C5 C 0.3888(5) 0.1027(5) 0.6826(7) 0.0361(17) Uani 1 1 d . . . . .
C6 C 0.4111(5) 0.1838(5) 0.7737(8) 0.0379(18) Uani 1 1 d . . . . .
H6 H 0.3677 0.2455 0.7748 0.045 Uiso 1 1 calc R U . . .
C7 C 0.4985(4) 0.1747(4) 0.8652(7) 0.0266(15) Uani 1 1 d . . . . .
H7 H 0.5155 0.2308 0.9295 0.032 Uiso 1 1 calc R U . . .
C8 C 0.7794(4) 0.0721(3) 0.7575(5) 0.0074(11) Uani 1 1 d . . . . .
H8A H 0.8172 0.1249 0.7013 0.009 Uiso 1 1 calc R U . . .
H8B H 0.7116 0.0562 0.7065 0.009 Uiso 1 1 calc R U . . .
C9 C 0.7521(4) 0.2380(3) 0.8854(5) 0.0077(11) Uani 1 1 d . . . . .
H9A H 0.7283 0.2682 0.9746 0.009 Uiso 1 1 calc R U . . .
H9B H 0.6997 0.2573 0.8094 0.009 Uiso 1 1 calc R U . . .
Co1 Co 1.0000 0.0000 0.5000 0.0068(2) Uani 1 2 d S . P . .
Co2 Co 1.09415(5) -0.09038(5) 0.96397(7) 0.00594(17) Uani 1 1 d . . . . .
F1 F 0.3044(3) 0.1124(3) 0.5896(5) 0.0646(14) Uani 1 1 d . . . . .
N1 N 0.7581(3) 0.1204(3) 0.8975(4) 0.0059(9) Uani 1 1 d . . . . .
O1 O 0.7786(3) -0.1385(2) 0.8149(4) 0.0109(8) Uani 1 1 d . . . . .
H1 H 0.7899 -0.1723 0.8913 0.016 Uiso 1 1 d R U . . .
O2 O 0.8948(2) -0.0734(2) 0.6298(3) 0.0084(7) Uani 1 1 d . . . . .
O3 O 0.9382(2) -0.0302(2) 0.8904(3) 0.0076(7) Uani 1 1 d . . . . .
O4 O 0.8881(3) 0.2975(2) 0.6881(3) 0.0119(8) Uani 1 1 d . . . . .
O5 O 0.9590(2) 0.2165(2) 0.9155(3) 0.0083(7) Uani 1 1 d . . . . .
O6 O 0.8811(2) 0.4073(2) 0.9108(3) 0.0092(7) Uani 1 1 d . . . . .
O7 O 1.1752(2) 0.0139(2) 0.8362(3) 0.0108(8) Uani 1 1 d . . . . .
H7A H 1.1722 -0.0130 0.7541 0.016 Uiso 1 1 d R U . . .
H7B H 1.1408 0.0721 0.8313 0.016 Uiso 1 1 d R U . . .
O8 O 1.0344(3) 0.1292(2) 0.6443(4) 0.0143(8) Uani 1 1 d . . . . .
H8C H 1.0523 0.1860 0.6029 0.021 Uiso 1 1 d R U . . .
H8D H 0.9850 0.1418 0.6987 0.021 Uiso 1 1 d R U . . .
O9 O 0.8329(3) 0.7169(2) 0.5561(4) 0.0151(8) Uani 1 1 d . . . . .
H9C H 0.8317 0.7830 0.5765 0.023 Uiso 1 1 d R U . . .
H9D H 0.8995 0.7139 0.5642 0.023 Uiso 1 1 d R U . . .
P1 P 0.85562(10) -0.04844(9) 0.77178(13) 0.0058(3) Uani 1 1 d . . . . .
P2 P 0.87950(10) 0.29616(9) 0.84702(13) 0.0064(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.500(6) . ?
C1 C2 1.515(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.385(7) . ?
C2 C7 1.399(7) . ?
C3 C4 1.388(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.361(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.356(9) . ?
C5 F1 1.365(7) . ?
C6 C7 1.386(8) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 N1 1.500(6) . ?
C8 P1 1.796(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N1 1.478(5) . ?
C9 P2 1.834(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
Co1 O6 2.059(3) 4_565 ?
Co1 O6 2.059(3) 2_746 ?
Co1 O2 2.081(3) 3_756 ?
Co1 O2 2.081(3) . ?
Co1 O8 2.152(3) . ?
Co1 O8 2.152(3) 3_756 ?
Co2 O4 2.036(3) 2_746 ?
Co2 O5 2.084(3) 3_757 ?
Co2 O7 2.091(3) . ?
Co2 O3 2.104(3) 3_757 ?
Co2 O3 2.209(3) . ?
Co2 N1 2.277(4) 3_757 ?
N1 Co2 2.277(4) 3_757 ?
O1 P1 1.563(3) . ?
O1 H1 0.8475 . ?
O2 P1 1.496(3) . ?
O3 P1 1.522(3) . ?
O3 Co2 2.104(3) 3_757 ?
O4 P2 1.522(3) . ?
O4 Co2 2.036(3) 2_756 ?
O5 P2 1.543(3) . ?
O5 Co2 2.084(3) 3_757 ?
O6 P2 1.518(3) . ?
O6 Co1 2.059(3) 2_756 ?
O7 H7A 0.8500 . ?
O7 H7B 0.8500 . ?
O8 H8C 0.8500 . ?
O8 H8D 0.8500 . ?
O9 H9C 0.8499 . ?
O9 H9D 0.8500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 115.5(4) . . ?
N1 C1 H1A 108.4 . . ?
C2 C1 H1A 108.4 . . ?
N1 C1 H1B 108.4 . . ?
C2 C1 H1B 108.4 . . ?
H1A C1 H1B 107.5 . . ?
C3 C2 C7 118.4(5) . . ?
C3 C2 C1 120.2(4) . . ?
C7 C2 C1 121.4(5) . . ?
C2 C3 C4 120.9(5) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 118.3(6) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C6 C5 C4 123.2(6) . . ?
C6 C5 F1 118.8(6) . . ?
C4 C5 F1 118.0(6) . . ?
C5 C6 C7 118.5(6) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C6 C7 C2 120.6(6) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
N1 C8 P1 113.0(3) . . ?
N1 C8 H8A 109.0 . . ?
P1 C8 H8A 109.0 . . ?
N1 C8 H8B 109.0 . . ?
P1 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
N1 C9 P2 111.6(3) . . ?
N1 C9 H9A 109.3 . . ?
P2 C9 H9A 109.3 . . ?
N1 C9 H9B 109.3 . . ?
P2 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
O6 Co1 O6 180.0 4_565 2_746 ?
O6 Co1 O2 89.41(12) 4_565 3_756 ?
O6 Co1 O2 90.59(12) 2_746 3_756 ?
O6 Co1 O2 90.59(12) 4_565 . ?
O6 Co1 O2 89.41(12) 2_746 . ?
O2 Co1 O2 180.0 3_756 . ?
O6 Co1 O8 87.88(12) 4_565 . ?
O6 Co1 O8 92.12(12) 2_746 . ?
O2 Co1 O8 85.97(12) 3_756 . ?
O2 Co1 O8 94.03(12) . . ?
O6 Co1 O8 92.12(12) 4_565 3_756 ?
O6 Co1 O8 87.88(12) 2_746 3_756 ?
O2 Co1 O8 94.03(12) 3_756 3_756 ?
O2 Co1 O8 85.97(12) . 3_756 ?
O8 Co1 O8 180.0 . 3_756 ?
O4 Co2 O5 85.36(12) 2_746 3_757 ?
O4 Co2 O7 86.69(13) 2_746 . ?
O5 Co2 O7 167.45(12) 3_757 . ?
O4 Co2 O3 174.19(12) 2_746 3_757 ?
O5 Co2 O3 95.84(12) 3_757 3_757 ?
O7 Co2 O3 93.04(13) . 3_757 ?
O4 Co2 O3 97.99(12) 2_746 . ?
O5 Co2 O3 96.94(12) 3_757 . ?
O7 Co2 O3 93.77(12) . . ?
O3 Co2 O3 76.23(13) 3_757 . ?
O4 Co2 N1 100.39(13) 2_746 3_757 ?
O5 Co2 N1 80.71(12) 3_757 3_757 ?
O7 Co2 N1 91.21(13) . 3_757 ?
O3 Co2 N1 85.42(13) 3_757 3_757 ?
O3 Co2 N1 161.20(13) . 3_757 ?
C9 N1 C1 111.6(3) . . ?
C9 N1 C8 110.0(3) . . ?
C1 N1 C8 111.8(3) . . ?
C9 N1 Co2 104.4(3) . 3_757 ?
C1 N1 Co2 113.1(3) . 3_757 ?
C8 N1 Co2 105.5(3) . 3_757 ?
P1 O1 H1 120.2 . . ?
P1 O2 Co1 134.17(19) . . ?
P1 O3 Co2 116.43(17) . 3_757 ?
P1 O3 Co2 139.78(19) . . ?
Co2 O3 Co2 103.77(13) 3_757 . ?
P2 O4 Co2 136.86(19) . 2_756 ?
P2 O5 Co2 119.83(18) . 3_757 ?
P2 O6 Co1 132.55(19) . 2_756 ?
Co2 O7 H7A 106.6 . . ?
Co2 O7 H7B 107.4 . . ?
H7A O7 H7B 106.8 . . ?
Co1 O8 H8C 112.6 . . ?
Co1 O8 H8D 113.2 . . ?
H8C O8 H8D 110.5 . . ?
H9C O9 H9D 92.9 . . ?
O2 P1 O3 116.82(19) . . ?
O2 P1 O1 109.12(18) . . ?
O3 P1 O1 109.52(19) . . ?
O2 P1 C8 108.1(2) . . ?
O3 P1 C8 106.42(19) . . ?
O1 P1 C8 106.3(2) . . ?
O6 P2 O4 112.78(18) . . ?
O6 P2 O5 115.33(18) . . ?
O4 P2 O5 110.42(19) . . ?
O6 P2 C9 106.19(19) . . ?
O4 P2 C9 108.1(2) . . ?
O5 P2 C9 103.26(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 92.1(6) . . . . ?
N1 C1 C2 C7 -86.7(6) . . . . ?
C7 C2 C3 C4 2.4(8) . . . . ?
C1 C2 C3 C4 -176.5(5) . . . . ?
C2 C3 C4 C5 0.0(9) . . . . ?
C3 C4 C5 C6 -2.8(10) . . . . ?
C3 C4 C5 F1 178.3(5) . . . . ?
C4 C5 C6 C7 2.9(10) . . . . ?
F1 C5 C6 C7 -178.2(5) . . . . ?
C5 C6 C7 C2 -0.3(9) . . . . ?
C3 C2 C7 C6 -2.3(8) . . . . ?
C1 C2 C7 C6 176.6(5) . . . . ?
P2 C9 N1 C1 168.4(3) . . . . ?
P2 C9 N1 C8 -66.9(4) . . . . ?
P2 C9 N1 Co2 45.9(3) . . . 3_757 ?
C2 C1 N1 C9 67.8(5) . . . . ?
C2 C1 N1 C8 -56.0(5) . . . . ?
C2 C1 N1 Co2 -174.9(3) . . . 3_757 ?
P1 C8 N1 C9 148.1(3) . . . . ?
P1 C8 N1 C1 -87.3(4) . . . . ?
P1 C8 N1 Co2 36.1(3) . . . 3_757 ?
Co1 O2 P1 O3 -53.2(3) . . . . ?
Co1 O2 P1 O1 -178.1(2) . . . . ?
Co1 O2 P1 C8 66.7(3) . . . . ?
Co2 O3 P1 O2 141.90(18) 3_757 . . . ?
Co2 O3 P1 O2 -36.2(4) . . . . ?
Co2 O3 P1 O1 -93.4(2) 3_757 . . . ?
Co2 O3 P1 O1 88.4(3) . . . . ?
Co2 O3 P1 C8 21.1(3) 3_757 . . . ?
Co2 O3 P1 C8 -157.0(3) . . . . ?
N1 C8 P1 O2 -165.7(3) . . . . ?
N1 C8 P1 O3 -39.5(4) . . . . ?
N1 C8 P1 O1 77.2(3) . . . . ?
Co1 O6 P2 O4 -94.6(3) 2_756 . . . ?
Co1 O6 P2 O5 33.6(3) 2_756 . . . ?
Co1 O6 P2 C9 147.3(3) 2_756 . . . ?
Co2 O4 P2 O6 2.3(4) 2_756 . . . ?
Co2 O4 P2 O5 -128.3(3) 2_756 . . . ?
Co2 O4 P2 C9 119.4(3) 2_756 . . . ?
Co2 O5 P2 O6 109.4(2) 3_757 . . . ?
Co2 O5 P2 O4 -121.3(2) 3_757 . . . ?
Co2 O5 P2 C9 -6.0(3) 3_757 . . . ?
N1 C9 P2 O6 -150.8(3) . . . . ?
N1 C9 P2 O4 88.0(3) . . . . ?
N1 C9 P2 O5 -29.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O9 H9D O5 0.85 1.81 2.655(4) 176.3 2_756
O9 H9C O2 0.85 2.02 2.819(4) 155.6 1_565
O9 H9C O1 0.85 2.59 3.159(5) 125.3 1_565
O9 H9C F1 0.85 2.64 3.052(5) 111.4 3_666
O8 H8D O5 0.85 2.30 3.003(5) 139.9 .
O8 H8D O4 0.85 2.31 2.858(4) 122.9 .
O8 H8C O9 0.85 2.47 3.244(5) 151.0 3_766
O8 H8C O5 0.85 2.42 3.032(5) 129.0 4_565
O7 H7B O9 0.85 2.12 2.743(4) 129.4 2_746
O7 H7B O8 0.85 2.30 2.883(4) 126.3 .
O7 H7A O6 0.85 1.95 2.767(4) 159.9 2_746
O1 H1 O9 0.85 1.73 2.560(5) 166.5 4_566

_refine_diff_density_max         0.599
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.128

