# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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 1452819'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H22 Cu3 O16 P4'
_chemical_formula_weight         760.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           81
_space_group_name_H-M_alt        'P -4'
_space_group_name_Hall           'P -4'

_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'
'y, -x, -z'
'-y, x, -z'

_cell_length_a                   16.134(2)
_cell_length_b                   16.134(2)
_cell_length_c                   4.5489(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1184.1(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    289(2)
_cell_measurement_reflns_used    5943
_cell_measurement_theta_min      3.57
_cell_measurement_theta_max      24.98

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.134
_exptl_crystal_F_000             762
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    3.019
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.805
_exptl_absorpt_correction_T_max  0.860
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      289(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5215
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.572
_diffrn_reflns_theta_max         24.976
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             2057
_reflns_number_gt                1532
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.962

_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 XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refined as a 2-component inversion twin.
;
_vrf_PLAT415_1                   
;
PROBLEM: Short Inter D-H..H-X  H1A .. H4A  ..  1.78 Ang.
RESPONSE: This could be caused by the poor quality of the crystal.
;
_vrf_PLAT090_1                   
;
PROBLEM: Poor Data Parameter Ratio (Zmax > 18)........ 6.02 Note 
RESPONSE: This could be caused by the poor quality of the crystal.
;
_vrf_PLAT201_1                   
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s)......3 Report 
RESPONSE: Three oxygen atoms are disordered.
;
_vrf_PLAT220_1                   
;
PROBLEM: Large Non-Solvent  O  Ueq(max) Ueq(min) Range 8.3 Ratio
RESPONSE: This could be caused by the poor quality of the crystal.
;
_vrf_PLAT341_1                   
;
PROBLEM: Low Bond Precision on  C-C Bonds .........0.01971 Ang.
RESPONSE: This could be caused by the poor quality of the crystal.
;
_vrf_PLAT420_1                   
;
PROBLEM:  D-H Without Acceptor O1W    --  H1W.
RESPONSE: This could be caused by the poor quality of the crystal.
;
_vrf_PLAT482_1                   
;
PROBLEM:  Small D-H..A Angle Rep for O1W ..  O2W ..89.30 Degree.
RESPONSE: This could be caused by the poor quality of the crystal.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0904P)²+10.0000P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.59(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2057
_refine_ls_number_parameters     195
_refine_ls_number_restraints     146
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1643
_refine_ls_wR_factor_gt          0.1454
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      0.976
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.19906(8) -0.46142(8) 1.5016(9) 0.0114(4) Uani 1 1 d . U . . .
Cu2 Cu 0.5000 0.0000 1.5005(12) 0.0078(5) Uani 1 2 d S T P . .
O1W O 0.2949(8) -0.5258(8) 1.351(3) 0.044(4) Uani 1 1 d . . . . .
H1W H 0.3192 -0.5560 1.4776 0.052 Uiso 1 1 d R U . . .
H2W H 0.2821 -0.5156 1.1737 0.052 Uiso 1 1 d R U . . .
O2W O 0.3808(16) -0.6052(15) 1.173(7) 0.119(9) Uani 1 1 d . U . . .
H3W H 0.3793 -0.6043 0.9864 0.143 Uiso 1 1 d R U . . .
H4W H 0.4156 -0.6409 1.2334 0.143 Uiso 1 1 d R U . . .
O1 O 0.0786(15) -0.3067(15) 2.173(6) 0.009(7) Uani 0.58(3) 1 d . U P A 1
H1A H 0.0455 -0.3451 2.1808 0.013 Uiso 1 1 calc R U . A 1
O2 O 0.1319(14) -0.3816(14) 1.754(5) 0.010(6) Uani 0.58(3) 1 d . U P A 1
O3 O 0.2197(17) -0.3787(16) 2.205(6) 0.011(7) Uani 0.58(3) 1 d . U P A 1
O1' O 0.221(2) -0.379(2) 1.782(9) 0.014(11) Uiso 0.42(3) 1 d . . P A 2
O2' O 0.134(2) -0.3908(19) 2.283(7) 0.012(9) Uiso 0.42(3) 1 d . . P A 2
O3' O 0.081(2) -0.306(2) 1.852(9) 0.013(10) Uiso 0.42(3) 1 d . . P A 2
O4 O 0.4573(19) -0.1949(18) 2.172(7) 0.011(8) Uani 0.48(3) 1 d . U P B 1
O5 O 0.477(2) -0.096(2) 1.758(7) 0.016(9) Uani 0.48(3) 1 d . U P B 1
O6 O 0.4162(17) -0.0385(17) 2.207(7) 0.006(7) Uani 0.48(3) 1 d . U P B 1
O4' O 0.4240(17) -0.0363(17) 1.781(7) 0.010(8) Uiso 0.52(3) 1 d . . P B 2
O5' O 0.4765(15) -0.0977(15) 2.272(5) 0.000(7) Uiso 0.52(3) 1 d . . P B 2
O6' O 0.4549(17) -0.1900(15) 1.826(6) 0.006(7) Uiso 0.52(3) 1 d . . P B 2
P1 P 0.15928(17) -0.33538(17) 1.998(2) 0.0091(6) Uani 1 1 d . U . . .
P2 P 0.42488(16) -0.11550(16) 1.9995(16) 0.0078(6) Uani 1 1 d . U . . .
C1 C 0.2072(9) -0.2394(9) 1.894(3) 0.018(3) Uani 1 1 d . U . . .
C2 C 0.2839(6) -0.2160(6) 2.007(5) 0.009(2) Uani 1 1 d . U . . .
H2A H 0.3106 -0.2477 2.1494 0.011 Uiso 1 1 calc R U . . .
C3 C 0.3200(9) -0.1414(9) 1.897(4) 0.021(4) Uani 1 1 d . U . . .
C4 C 0.2786(9) -0.0912(9) 1.695(3) 0.015(3) Uani 1 1 d . U . . .
H4A H 0.3025 -0.0418 1.6320 0.018 Uiso 1 1 calc R U . . .
C5 C 0.2006(9) -0.1156(9) 1.587(3) 0.018(4) Uani 1 1 d . U . . .
C6 C 0.1667(11) -0.1880(11) 1.681(4) 0.025(4) Uani 1 1 d . U . . .
H6A H 0.1159 -0.2047 1.6047 0.030 Uiso 1 1 calc R U . . .
C7 C 0.1530(12) -0.0612(12) 1.381(4) 0.035(5) Uani 1 1 d . U . . .
H7A H 0.1010 -0.0870 1.3339 0.052 Uiso 1 1 calc R U . . .
H7B H 0.1844 -0.0533 1.2037 0.052 Uiso 1 1 calc R U . . .
H7C H 0.1431 -0.0085 1.4720 0.052 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2' 1.84(3) 1_554 ?
Cu1 O1' 1.88(4) . ?
Cu1 O3 1.93(3) 1_554 ?
Cu1 O4 1.98(3) 4_549 ?
Cu1 O1W 1.984(12) . ?
Cu1 O6' 2.01(3) 4_548 ?
Cu1 O2 2.04(2) . ?
Cu1 O5' 2.18(2) 4_549 ?
Cu1 O5 2.26(3) 4_548 ?
Cu2 O4' 1.87(3) . ?
Cu2 O4' 1.87(3) 2_655 ?
Cu2 O5' 1.93(2) 1_554 ?
Cu2 O5' 1.93(2) 2_654 ?
Cu2 O5 1.98(3) . ?
Cu2 O5 1.98(3) 2_655 ?
Cu2 O6 2.00(3) 1_554 ?
Cu2 O6 2.00(3) 2_654 ?
O1 P1 1.59(3) . ?
O2 P1 1.41(2) . ?
O3 P1 1.52(3) . ?
O3 Cu1 1.93(3) 1_556 ?
O1' P1 1.57(4) . ?
O2' P1 1.63(3) . ?
O2' Cu1 1.84(3) 1_556 ?
O3' P1 1.51(4) . ?
O4 P2 1.59(3) . ?
O4 Cu1 1.98(3) 3_659 ?
O5 P2 1.42(3) . ?
O5 Cu1 2.26(3) 3_658 ?
O6 P2 1.57(3) . ?
O6 Cu2 2.00(3) 1_556 ?
O4' P2 1.62(3) . ?
O5' P2 1.52(2) . ?
O5' Cu2 1.93(2) 1_556 ?
O5' Cu1 2.18(2) 3_659 ?
O6' P2 1.52(3) . ?
O6' Cu1 2.01(3) 3_658 ?
P1 C1 1.794(16) . ?
P2 C3 1.805(15) . ?
C1 C2 1.39(2) . ?
C1 C6 1.44(2) . ?
C2 C3 1.43(2) . ?
C3 C4 1.39(2) . ?
C4 C5 1.41(2) . ?
C5 C6 1.36(2) . ?
C5 C7 1.50(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2' Cu1 O1' 91.9(16) 1_554 . ?
O3 Cu1 O4 171.4(12) 1_554 4_549 ?
O2' Cu1 O1W 125.7(11) 1_554 . ?
O1' Cu1 O1W 117.3(13) . . ?
O3 Cu1 O1W 89.2(9) 1_554 . ?
O4 Cu1 O1W 86.4(10) 4_549 . ?
O2' Cu1 O6' 88.5(13) 1_554 4_548 ?
O1' Cu1 O6' 172.2(15) . 4_548 ?
O1W Cu1 O6' 56.7(8) . 4_548 ?
O3 Cu1 O2 92.8(10) 1_554 . ?
O4 Cu1 O2 88.8(11) 4_549 . ?
O1W Cu1 O2 160.0(8) . . ?
O2' Cu1 O5' 96.4(11) 1_554 4_549 ?
O1' Cu1 O5' 98.4(13) . 4_549 ?
O1W Cu1 O5' 120.5(7) . 4_549 ?
O6' Cu1 O5' 89.3(10) 4_548 4_549 ?
O3 Cu1 O5 93.6(11) 1_554 4_548 ?
O4 Cu1 O5 94.5(12) 4_549 4_548 ?
O1W Cu1 O5 99.4(9) . 4_548 ?
O2 Cu1 O5 100.3(10) . 4_548 ?
O4' Cu2 O4' 93.6(19) . 2_655 ?
O4' Cu2 O5' 89.1(11) . 1_554 ?
O4' Cu2 O5' 139.1(11) 2_655 1_554 ?
O4' Cu2 O5' 139.1(11) . 2_654 ?
O4' Cu2 O5' 89.1(11) 2_655 2_654 ?
O5' Cu2 O5' 114.6(14) 1_554 2_654 ?
O5 Cu2 O5 107.3(19) . 2_655 ?
O5 Cu2 O6 91.6(13) . 1_554 ?
O5 Cu2 O6 139.8(13) 2_655 1_554 ?
O5 Cu2 O6 139.8(13) . 2_654 ?
O5 Cu2 O6 91.6(13) 2_655 2_654 ?
O6 Cu2 O6 96.1(18) 1_554 2_654 ?
P1 O2 Cu1 127.7(14) . . ?
P1 O3 Cu1 129.7(17) . 1_556 ?
P1 O1' Cu1 129(2) . . ?
P1 O2' Cu1 128.8(19) . 1_556 ?
P2 O4 Cu1 127.9(17) . 3_659 ?
P2 O5 Cu2 138(2) . . ?
P2 O5 Cu1 120.1(19) . 3_658 ?
Cu2 O5 Cu1 100.7(13) . 3_658 ?
P2 O6 Cu2 126.1(17) . 1_556 ?
P2 O4' Cu2 131.5(17) . . ?
P2 O5' Cu2 134.6(15) . 1_556 ?
P2 O5' Cu1 119.8(14) . 3_659 ?
Cu2 O5' Cu1 105.6(11) 1_556 3_659 ?
P2 O6' Cu1 131.0(15) . 3_658 ?
O2 P1 O3 116.4(14) . . ?
O3' P1 O1' 113(2) . . ?
O2 P1 O1 106.9(13) . . ?
O3 P1 O1 110.4(15) . . ?
O3' P1 O2' 108.4(18) . . ?
O1' P1 O2' 114.6(17) . . ?
O2 P1 C1 112.6(11) . . ?
O3' P1 C1 88.4(15) . . ?
O3 P1 C1 106.4(12) . . ?
O1' P1 C1 86.9(15) . . ?
O1 P1 C1 103.4(10) . . ?
O2' P1 C1 142.4(13) . . ?
O6' P2 O5' 113.5(15) . . ?
O5 P2 O6 110.1(18) . . ?
O5 P2 O4 111.2(18) . . ?
O6 P2 O4 111.8(16) . . ?
O6' P2 O4' 107.9(14) . . ?
O5' P2 O4' 110.9(14) . . ?
O5 P2 C3 114.2(14) . . ?
O6' P2 C3 88.9(12) . . ?
O5' P2 C3 140.3(11) . . ?
O6 P2 C3 104.9(11) . . ?
O4 P2 C3 104.5(12) . . ?
O4' P2 C3 90.9(11) . . ?
C2 C1 C6 119.8(15) . . ?
C2 C1 P1 121.4(12) . . ?
C6 C1 P1 118.7(12) . . ?
C1 C2 C3 117.5(16) . . ?
C4 C3 C2 121.7(15) . . ?
C4 C3 P2 119.0(12) . . ?
C2 C3 P2 119.1(12) . . ?
C3 C4 C5 119.7(14) . . ?
C6 C5 C4 119.4(15) . . ?
C6 C5 C7 119.6(15) . . ?
C4 C5 C7 120.9(14) . . ?
C5 C6 C1 121.8(16) . . ?

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
O1W H1W O2W 0.85 1.88 2.05(3) 89.3 .

_refine_diff_density_max         1.477
_refine_diff_density_min         -0.658
_refine_diff_density_rms         0.197

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1452820'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H20 Cu N2 O10 P2'
_chemical_formula_weight         465.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           58
_space_group_name_H-M_alt        'P n n m'
_space_group_name_Hall           '-P 2 2n'

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

_cell_length_a                   14.7117(19)
_cell_length_b                   9.0337(11)
_cell_length_c                   13.8590(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1841.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9331
_cell_measurement_theta_min      2.02
_cell_measurement_theta_max      27.54

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_F_000             956
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.412
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.720
_exptl_absorpt_correction_T_max  0.868
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8779
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.019
_diffrn_reflns_theta_max         27.538
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2187
_reflns_number_gt                1508
_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 XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_vrf_PLAT420_2                   
;
PROBLEM: D-H Without Acceptor O2W --H3W.
RESPONSE: This could be caused by the poor quality of the crystal.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0664P)²+1.8854P]
 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         2187
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1262
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   0.950
_refine_ls_restrained_S_all      0.950
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.0000 0.24856(4) 0.01690(19) Uani 1 2 d S T P . .
O1 O 0.26473(17) -0.0828(3) 0.18065(17) 0.0238(6) Uani 1 1 d . . . . .
O1W O -0.0314(2) 0.2548(3) 0.25051(18) 0.0351(7) Uani 1 1 d . . . . .
H1W H -0.0011 0.3079 0.2896 0.042 Uiso 1 1 d R U . . .
H2W H -0.0833 0.2943 0.2584 0.042 Uiso 1 1 d R U . . .
O2W O 0.4353(2) -0.1141(4) 0.1009(2) 0.0439(8) Uani 1 1 d . . . . .
H3W H 0.3989 -0.1807 0.0812 0.053 Uiso 1 1 d R U . . .
H4W H 0.4198 -0.0260 0.0870 0.053 Uiso 1 1 d R U . . .
O2 O 0.12826(16) 0.0543(3) 0.25236(16) 0.0239(6) Uani 1 1 d . . . . .
O3 O 0.28465(15) 0.1600(3) 0.26223(16) 0.0218(5) Uani 1 1 d . . . . .
H3B H 0.2602 0.2391 0.2752 0.033 Uiso 1 1 calc R U . . .
N1 N 0.0000 0.0000 0.1005(3) 0.0193(9) Uani 1 2 d S T P . .
N2 N 0.0000 0.0000 0.3997(3) 0.0230(9) Uani 1 2 d S T P . .
P1 P 0.21768(5) 0.06205(9) 0.20058(6) 0.0150(2) Uani 1 1 d . . . . .
C1 C 0.2182(3) 0.0859(5) 0.0000 0.0161(9) Uani 1 2 d S T P . .
H1A H 0.2361 -0.0128 0.0000 0.019 Uiso 1 2 calc R U P . .
C2 C 0.2049(2) 0.1593(4) 0.0873(2) 0.0163(7) Uani 1 1 d . . . . .
C3 C 0.1796(2) 0.3079(4) 0.0864(2) 0.0204(7) Uani 1 1 d . . . . .
H3A H 0.1706 0.3573 0.1445 0.025 Uiso 1 1 calc R U . . .
C4 C 0.1676(4) 0.3835(5) 0.0000 0.0232(11) Uani 1 2 d S T P . .
C5 C 0.1406(5) 0.5444(7) 0.0000 0.0489(19) Uani 1 2 d S T P . .
H5A H 0.1352 0.5786 -0.0653 0.073 Uiso 0.5 1 calc R U P . .
H5B H 0.1862 0.6013 0.0329 0.073 Uiso 0.5 1 calc R U P . .
H5C H 0.0834 0.5556 0.0324 0.073 Uiso 0.5 1 calc R U P . .
C6 C -0.0156(2) 0.1235(4) 0.0498(3) 0.0217(8) Uani 1 1 d . . . . .
H6A H -0.0268 0.2115 0.0824 0.026 Uiso 1 1 calc R U . . .
C7 C -0.0741(2) 0.0342(5) 0.4498(3) 0.0364(11) Uani 1 1 d . . . . .
H7A H -0.1272 0.0587 0.4170 0.044 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.950(2) . ?
Cu1 O2 1.950(2) 2 ?
Cu1 N1 2.053(4) . ?
Cu1 N2 2.095(4) . ?
Cu1 O1W 2.348(3) 2 ?
Cu1 O1W 2.348(3) . ?
O1 P1 1.506(2) . ?
O2 P1 1.500(2) . ?
O3 P1 1.576(2) . ?
N1 C6 1.338(4) . ?
N1 C6 1.338(4) 2 ?
N2 C7 1.328(4) . ?
N2 C7 1.328(4) 2 ?
P1 C2 1.809(3) . ?
C1 C2 1.394(4) 6 ?
C1 C2 1.394(4) . ?
C2 C3 1.393(4) . ?
C3 C4 1.389(4) . ?
C4 C3 1.389(4) 6 ?
C4 C5 1.506(7) . ?
C6 C6 1.379(7) 6 ?
C7 C7 1.392(7) 6_556 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 176.91(13) . 2 ?
O2 Cu1 N1 91.55(7) . . ?
O2 Cu1 N1 91.55(7) 2 . ?
O2 Cu1 N2 88.45(7) . . ?
O2 Cu1 N2 88.45(7) 2 . ?
N1 Cu1 N2 180.0 . . ?
O2 Cu1 O1W 93.21(11) . 2 ?
O2 Cu1 O1W 86.76(11) 2 2 ?
N1 Cu1 O1W 90.66(6) . 2 ?
N2 Cu1 O1W 89.34(6) . 2 ?
O2 Cu1 O1W 86.76(11) . . ?
O2 Cu1 O1W 93.21(11) 2 . ?
N1 Cu1 O1W 90.66(6) . . ?
N2 Cu1 O1W 89.34(6) . . ?
O1W Cu1 O1W 178.68(13) 2 . ?
P1 O2 Cu1 147.91(15) . . ?
C6 N1 C6 116.6(4) . 2 ?
C6 N1 Cu1 121.7(2) . . ?
C6 N1 Cu1 121.7(2) 2 . ?
C7 N2 C7 117.0(4) . 2 ?
C7 N2 Cu1 121.5(2) . . ?
C7 N2 Cu1 121.5(2) 2 . ?
O2 P1 O1 116.77(16) . . ?
O2 P1 O3 108.37(14) . . ?
O1 P1 O3 107.46(14) . . ?
O2 P1 C2 110.26(14) . . ?
O1 P1 C2 108.11(14) . . ?
O3 P1 C2 105.23(14) . . ?
C2 C1 C2 120.5(4) 6 . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 P1 120.3(3) . . ?
C1 C2 P1 120.5(3) . . ?
C4 C3 C2 121.1(3) . . ?
C3 C4 C3 119.0(5) . 6 ?
C3 C4 C5 120.5(2) . . ?
C3 C4 C5 120.5(2) 6 . ?
N1 C6 C6 121.7(2) . 6 ?
N2 C7 C7 121.5(2) . 6_556 ?

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
O1W H1W O2W 0.85 1.93 2.765(4) 165.6 3
O1W H2W O3 0.85 2.01 2.819(4) 159.7 4_455
O2W H3W O1 0.85 2.56 2.756(4) 93.9 .
O2W H4W O2W 0.85 2.49 2.807(6) 103.2 2_655
O2W H3W O2W 0.85 2.65 2.797(6) 91.1 6
O3 H3B O1 0.82 1.76 2.560(3) 164.6 3
C1 H1A O1 0.93 2.62 3.010(3) 106.1 .
C1 H1A O1 0.93 2.62 3.010(3) 106.1 6
C7 H7A O2 0.93 2.50 2.960(4) 110.8 2

_refine_diff_density_max         0.407
_refine_diff_density_min         -0.935
_refine_diff_density_rms         0.112

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1452821'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 Cu N2 O6 P2'
_chemical_formula_weight         469.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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                   8.539(5)
_cell_length_b                   8.948(5)
_cell_length_c                   12.706(8)
_cell_angle_alpha                95.020(11)
_cell_angle_beta                 107.860(10)
_cell_angle_gamma                103.549(10)
_cell_volume                     885.0(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8373
_cell_measurement_theta_min      1.71
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_F_000             478
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    1.455
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_T_max  0.816
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7099
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_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         1.709
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             3110
_reflns_number_gt                2658
_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 XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0396P)²+0.5720P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3110
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0808
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.67613(4) 0.67465(4) 0.90288(3) 0.01943(12) Uani 1 1 d . . . . .
O1 O 0.6536(3) 0.6243(2) 0.62081(17) 0.0251(5) Uani 1 1 d . . . . .
O2 O 0.4968(2) 0.3367(2) 0.57547(17) 0.0245(5) Uani 1 1 d . . . . .
H2B H 0.4622 0.3667 0.5157 0.037 Uiso 1 1 calc R U . . .
O3 O 0.6550(2) 0.4672(2) 0.77759(16) 0.0231(5) Uani 1 1 d . . . . .
O4 O 1.4316(2) 0.6020(2) 0.87714(17) 0.0226(5) Uani 1 1 d . . . . .
O5 O 1.4133(2) 0.3145(2) 0.84260(17) 0.0251(5) Uani 1 1 d . . . . .
H5A H 1.4925 0.3548 0.8216 0.038 Uiso 1 1 calc R U . . .
O6 O 1.2516(2) 0.4077(3) 0.95942(17) 0.0259(5) Uani 1 1 d . . . . .
N1 N 0.6422(3) 0.8386(3) 0.8066(2) 0.0207(5) Uani 1 1 d . . . . .
N2 N 0.9220(3) 0.7780(3) 0.9214(2) 0.0223(6) Uani 1 1 d . . . . .
P1 P 0.64994(9) 0.46475(9) 0.65711(6) 0.01790(18) Uani 1 1 d . . . . .
P2 P 1.31851(9) 0.43909(9) 0.86397(6) 0.01770(18) Uani 1 1 d . . . . .
C1 C 0.4911(4) 0.8595(4) 0.7499(3) 0.0286(7) Uani 1 1 d . . . . .
H1A H 0.3929 0.8019 0.7604 0.034 Uiso 1 1 calc R U . . .
C2 C 0.4764(5) 0.9640(4) 0.6762(3) 0.0396(9) Uani 1 1 d . . . . .
H2A H 0.3703 0.9792 0.6396 0.048 Uiso 1 1 calc R U . . .
C3 C 0.6199(5) 1.0453(4) 0.6577(3) 0.0390(9) Uani 1 1 d . . . . .
H3A H 0.6115 1.1131 0.6061 0.047 Uiso 1 1 calc R U . . .
C4 C 0.7768(4) 1.0260(4) 0.7160(3) 0.0331(8) Uani 1 1 d . . . . .
H4A H 0.8758 1.0817 0.7055 0.040 Uiso 1 1 calc R U . . .
C5 C 0.7841(4) 0.9216(3) 0.7908(2) 0.0222(6) Uani 1 1 d . . . . .
C6 C 0.9440(4) 0.8903(3) 0.8588(2) 0.0212(6) Uani 1 1 d . . . . .
C7 C 1.1063(4) 0.9706(4) 0.8615(3) 0.0324(8) Uani 1 1 d . . . . .
H7A H 1.1200 1.0496 0.8194 0.039 Uiso 1 1 calc R U . . .
C8 C 1.2472(4) 0.9307(4) 0.9282(3) 0.0354(8) Uani 1 1 d . . . . .
H8A H 1.3567 0.9824 0.9309 0.042 Uiso 1 1 calc R U . . .
C9 C 1.2241(4) 0.8139(4) 0.9905(3) 0.0344(8) Uani 1 1 d . . . . .
H9A H 1.3172 0.7844 1.0344 0.041 Uiso 1 1 calc R U . . .
C10 C 1.0598(4) 0.7414(4) 0.9865(3) 0.0275(7) Uani 1 1 d . . . . .
H10A H 1.0443 0.6650 1.0303 0.033 Uiso 1 1 calc R U . . .
C11 C 0.9866(4) 0.2196(4) 0.4312(3) 0.0355(8) Uani 1 1 d . . . . .
H11A H 0.8788 0.2080 0.3737 0.053 Uiso 1 1 calc R U . . .
H11B H 1.0033 0.1185 0.4404 0.053 Uiso 1 1 calc R U . . .
H11C H 1.0773 0.2800 0.4100 0.053 Uiso 1 1 calc R U . . .
C12 C 0.9873(4) 0.3016(4) 0.5402(2) 0.0232(7) Uani 1 1 d . . . . .
C13 C 1.1308(4) 0.3328(4) 0.6370(2) 0.0233(7) Uani 1 1 d . . . . .
H13A H 1.2278 0.3059 0.6329 0.028 Uiso 1 1 calc R U . . .
C14 C 1.1325(3) 0.4032(3) 0.7398(2) 0.0188(6) Uani 1 1 d . . . . .
C15 C 0.9860(3) 0.4433(3) 0.7454(2) 0.0199(6) Uani 1 1 d . . . . .
H15A H 0.9851 0.4887 0.8138 0.024 Uiso 1 1 calc R U . . .
C16 C 0.8411(3) 0.4162(3) 0.6496(2) 0.0172(6) Uani 1 1 d . . . . .
C17 C 0.8451(4) 0.3468(3) 0.5481(2) 0.0209(6) Uani 1 1 d . . . . .
H17A H 0.7500 0.3301 0.4837 0.025 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O6 1.940(2) 2_767 ?
Cu1 O4 1.949(2) 1_455 ?
Cu1 N1 2.007(3) . ?
Cu1 N2 2.017(3) . ?
Cu1 O3 2.273(2) . ?
O1 P1 1.535(2) . ?
O2 P1 1.535(2) . ?
O3 P1 1.516(2) . ?
O4 P2 1.511(2) . ?
O4 Cu1 1.949(2) 1_655 ?
O5 P2 1.574(2) . ?
O6 P2 1.512(2) . ?
O6 Cu1 1.940(2) 2_767 ?
N1 C1 1.336(4) . ?
N1 C5 1.347(4) . ?
N2 C10 1.345(4) . ?
N2 C6 1.350(4) . ?
P1 C16 1.811(3) . ?
P2 C14 1.803(3) . ?
C1 C2 1.380(5) . ?
C2 C3 1.370(5) . ?
C3 C4 1.377(5) . ?
C4 C5 1.388(4) . ?
C5 C6 1.479(4) . ?
C6 C7 1.392(4) . ?
C7 C8 1.386(5) . ?
C8 C9 1.379(5) . ?
C9 C10 1.384(4) . ?
C11 C12 1.508(4) . ?
C12 C17 1.395(4) . ?
C12 C13 1.395(4) . ?
C13 C14 1.394(4) . ?
C14 C15 1.399(4) . ?
C15 C16 1.399(4) . ?
C16 C17 1.395(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Cu1 O4 95.88(8) 2_767 1_455 ?
O6 Cu1 N1 156.83(10) 2_767 . ?
O4 Cu1 N1 91.69(9) 1_455 . ?
O6 Cu1 N2 90.63(9) 2_767 . ?
O4 Cu1 N2 171.67(9) 1_455 . ?
N1 Cu1 N2 80.34(10) . . ?
O6 Cu1 O3 99.29(9) 2_767 . ?
O4 Cu1 O3 90.17(8) 1_455 . ?
N1 Cu1 O3 102.56(10) . . ?
N2 Cu1 O3 93.91(9) . . ?
P1 O3 Cu1 127.72(12) . . ?
P2 O4 Cu1 130.27(12) . 1_655 ?
P2 O6 Cu1 136.20(13) . 2_767 ?
C1 N1 C5 118.9(3) . . ?
C1 N1 Cu1 125.3(2) . . ?
C5 N1 Cu1 115.4(2) . . ?
C10 N2 C6 119.2(3) . . ?
C10 N2 Cu1 125.9(2) . . ?
C6 N2 Cu1 114.85(19) . . ?
O3 P1 O1 112.43(12) . . ?
O3 P1 O2 111.90(12) . . ?
O1 P1 O2 111.01(12) . . ?
O3 P1 C16 106.83(12) . . ?
O1 P1 C16 107.60(12) . . ?
O2 P1 C16 106.72(13) . . ?
O4 P2 O6 115.40(12) . . ?
O4 P2 O5 110.27(12) . . ?
O6 P2 O5 109.94(12) . . ?
O4 P2 C14 109.20(12) . . ?
O6 P2 C14 106.04(13) . . ?
O5 P2 C14 105.45(13) . . ?
N1 C1 C2 122.0(3) . . ?
C3 C2 C1 119.1(3) . . ?
C2 C3 C4 119.6(3) . . ?
C3 C4 C5 118.6(3) . . ?
N1 C5 C4 121.7(3) . . ?
N1 C5 C6 114.2(3) . . ?
C4 C5 C6 124.1(3) . . ?
N2 C6 C7 121.4(3) . . ?
N2 C6 C5 114.7(2) . . ?
C7 C6 C5 123.9(3) . . ?
C8 C7 C6 118.7(3) . . ?
C9 C8 C7 119.7(3) . . ?
C8 C9 C10 118.8(3) . . ?
N2 C10 C9 122.1(3) . . ?
C17 C12 C13 118.0(3) . . ?
C17 C12 C11 121.4(3) . . ?
C13 C12 C11 120.6(3) . . ?
C14 C13 C12 121.7(3) . . ?
C13 C14 C15 118.8(3) . . ?
C13 C14 P2 120.7(2) . . ?
C15 C14 P2 120.5(2) . . ?
C16 C15 C14 121.0(3) . . ?
C17 C16 C15 118.4(3) . . ?
C17 C16 P1 120.5(2) . . ?
C15 C16 P1 121.1(2) . . ?
C12 C17 C16 122.0(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 H2B O1 0.82 1.73 2.528(3) 163.0 2_666
O5 H5A O3 0.82 1.78 2.595(3) 171.8 1_655
C1 H1A O4 0.93 2.44 2.965(4) 115.8 1_455
C3 H3A O2 0.93 2.44 3.175(4) 136.4 1_565
C10 H10A O6 0.93 2.50 2.990(4) 112.8 2_767


_refine_diff_density_max         0.414
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.073

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1452822'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H20 Cu N2 O8 P2'
_chemical_formula_weight         505.83

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'
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           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'

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

_cell_length_a                   9.054(4)
_cell_length_b                   11.097(5)
_cell_length_c                   11.481(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.25(3)
_cell_angle_gamma                90
_cell_volume                     1059.8(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5352
_cell_measurement_theta_min      1.84
_cell_measurement_theta_max      24.99

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_F_000             518
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    1.228
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_correction_T_max  0.822
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4412
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.835
_diffrn_reflns_theta_max         24.987
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.945
_reflns_number_total             1816
_reflns_number_gt                1388
_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 XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0381P)²+0.2253P]
 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         1816
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.0000 0.17945(5) 1.2500 0.0200(2) Uani 1 2 d S T P A .
N1 N 1.0000 0.3619(3) 1.2500 0.0223(10) Uani 1 2 d S T P . .
N2 N 1.0000 0.9988(4) 1.2500 0.0211(9) Uani 1 2 d S T P . .
O1 O 0.5691(3) 0.1426(2) 1.0898(2) 0.0329(6) Uani 1 1 d . . . . .
H1A H 0.4914 0.0972 1.0638 0.049 Uiso 1 1 d R U . . .
O1W O 1.2164(3) 0.1953(2) 1.1556(2) 0.0429(7) Uani 1 1 d . . . . .
H1W H 1.2402 0.1674 1.0962 0.064 Uiso 1 1 d R U . A .
H2W H 1.2995 0.1698 1.2168 0.064 Uiso 1 1 d R U . . .
O2 O 0.6789(3) -0.0076(2) 0.97691(19) 0.0246(6) Uani 1 1 d . . . . .
O3 O 0.8339(3) 0.1844(2) 1.07895(19) 0.0237(6) Uani 1 1 d . . . . .
P1 P 0.67311(11) 0.12410(8) 1.00949(8) 0.0212(2) Uani 1 1 d . . . . .
C1 C 0.5616(11) 0.5312(7) 0.7346(10) 0.061(3) Uani 0.5 1 d . . P . .
H1B H 0.5325 0.5568 0.6485 0.092 Uiso 0.5 1 d R U P . .
H1C H 0.4941 0.5710 0.7696 0.092 Uiso 0.5 1 d R U P . .
H1D H 0.6719 0.5516 0.7837 0.092 Uiso 0.5 1 d R U P . .
C2 C 0.5349(12) 0.3959(6) 0.7361(9) 0.028(2) Uani 0.5 1 d . . P . .
C3 C 0.5732(6) 0.3309(4) 0.8618(4) 0.0695(18) Uani 1 1 d . . . . .
H3A H 0.5950 0.3751 0.9387 0.083 Uiso 1 1 d R U . . .
C4 C 0.5753(4) 0.2063(3) 0.8639(3) 0.0278(9) Uani 1 1 d . . . . .
C5 C 0.5000 0.1455(5) 0.7500 0.0259(12) Uani 1 2 d S T P . .
H5A H 0.5000 0.0617 0.7500 0.031 Uiso 1 2 calc R U P . .
C6 C 1.0283(9) 0.4241(6) 1.3553(6) 0.033(2) Uani 0.523(6) 1 d . . P A 1
H6A H 1.0485 0.3821 1.4301 0.039 Uiso 0.523(6) 1 calc R U P A 1
C7 C 1.0291(10) 0.5482(6) 1.3586(6) 0.036(2) Uani 0.523(6) 1 d . . P A 1
H7A H 1.0495 0.5878 1.4348 0.043 Uiso 0.523(6) 1 calc R U P A 1
C6' C 0.8711(10) 0.4255(8) 1.2351(10) 0.050(3) Uani 0.477(6) 1 d . . P A 2
H6'A H 0.7774 0.3838 1.2238 0.059 Uiso 0.477(6) 1 calc R U P A 2
C7' C 0.8651(11) 0.5504(7) 1.2350(10) 0.051(3) Uani 0.477(6) 1 d . . P A 2
H7'A H 0.7703 0.5900 1.2248 0.061 Uiso 0.477(6) 1 calc R U P A 2
C8 C 1.0000 0.6144(4) 1.2500 0.0243(12) Uani 1 2 d S T P . .
C9 C 1.0000 0.7482(4) 1.2500 0.0220(11) Uani 1 2 d S T P A .
C10 C 1.0478(5) 0.8133(3) 1.1676(4) 0.0346(10) Uani 1 1 d . . . . .
H10A H 1.0811 0.7736 1.1109 0.042 Uiso 1 1 calc R U . A .
C11 C 1.0456(5) 0.9360(3) 1.1708(3) 0.0310(9) Uani 1 1 d . . . . .
H11A H 1.0776 0.9783 1.1147 0.037 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O3 1.947(2) 2_757 ?
Cu1 O3 1.947(2) . ?
Cu1 N2 2.005(4) 1_545 ?
Cu1 N1 2.024(4) . ?
Cu1 O1W 2.592(3) . ?
N1 C6' 1.316(9) 2_757 ?
N1 C6' 1.316(9) . ?
N1 C6 1.326(7) . ?
N1 C6 1.326(7) 2_757 ?
N2 C11 1.333(4) . ?
N2 C11 1.333(4) 2_757 ?
N2 Cu1 2.005(4) 1_565 ?
O1 P1 1.570(3) . ?
O1 H1A 0.8200 . ?
O1W H1W 0.8500 . ?
O1W H2W 0.8500 . ?
O2 P1 1.515(3) . ?
O3 P1 1.512(2) . ?
P1 C4 1.800(3) . ?
C1 C1 1.296(19) 2_656 ?
C1 C2 1.522(10) . ?
C1 C2 1.834(10) 2_656 ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?
C2 C2 0.814(13) 2_656 ?
C2 C3 1.369(10) 2_656 ?
C2 C3 1.526(9) . ?
C2 C1 1.834(10) 2_656 ?
C3 C2 1.369(10) 2_656 ?
C3 C4 1.383(5) . ?
C3 H3A 0.9599 . ?
C4 C5 1.388(4) . ?
C5 C4 1.388(4) 2_656 ?
C5 H5A 0.9300 . ?
C6 C7 1.378(9) . ?
C6 H6A 0.9300 . ?
C7 C8 1.380(7) . ?
C7 H7A 0.9300 . ?
C6' C7' 1.387(11) . ?
C6' H6'A 0.9300 . ?
C7' C8 1.363(9) . ?
C7' H7'A 0.9300 . ?
C8 C7' 1.363(9) 2_757 ?
C8 C7 1.380(7) 2_757 ?
C8 C9 1.485(6) . ?
C9 C10 1.388(4) . ?
C9 C10 1.388(4) 2_757 ?
C10 C11 1.363(5) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?

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
O3 Cu1 O3 176.76(14) 2_757 . ?
O3 Cu1 N2 91.62(7) 2_757 1_545 ?
O3 Cu1 N2 91.62(7) . 1_545 ?
O3 Cu1 N1 88.38(7) 2_757 . ?
O3 Cu1 N1 88.38(7) . . ?
N2 Cu1 N1 180.0 1_545 . ?
O3 Cu1 O1W 90.55(10) 2_757 . ?
O3 Cu1 O1W 89.23(9) . . ?
N2 Cu1 O1W 93.90(6) 1_545 . ?
N1 Cu1 O1W 86.10(6) . . ?
C6' N1 C6' 115.1(8) 2_757 . ?
C6 N1 C6 117.3(7) . 2_757 ?
C6' N1 Cu1 122.5(4) 2_757 . ?
C6' N1 Cu1 122.5(4) . . ?
C6 N1 Cu1 121.4(3) . . ?
C6 N1 Cu1 121.4(3) 2_757 . ?
C11 N2 C11 117.1(4) . 2_757 ?
C11 N2 Cu1 121.5(2) . 1_565 ?
C11 N2 Cu1 121.5(2) 2_757 1_565 ?
P1 O1 H1A 109.5 . . ?
Cu1 O1W H1W 141.5 . . ?
Cu1 O1W H2W 101.5 . . ?
H1W O1W H2W 96.9 . . ?
P1 O3 Cu1 135.97(14) . . ?
O3 P1 O2 115.93(14) . . ?
O3 P1 O1 107.95(13) . . ?
O2 P1 O1 111.01(14) . . ?
O3 P1 C4 106.49(16) . . ?
O2 P1 C4 108.18(15) . . ?
O1 P1 C4 106.83(16) . . ?
C1 C1 C2 80.8(5) 2_656 . ?
C1 C1 C2 55.0(4) 2_656 2_656 ?
C2 C1 C2 26.0(4) . 2_656 ?
C1 C1 H1B 111.4 2_656 . ?
C2 C1 H1B 108.8 . . ?
C2 C1 H1B 118.3 2_656 . ?
C1 C1 H1C 29.4 2_656 . ?
C2 C1 H1C 108.6 . . ?
C2 C1 H1C 82.6 2_656 . ?
H1B C1 H1C 109.5 . . ?
C1 C1 H1D 130.4 2_656 . ?
C2 C1 H1D 111.0 . . ?
C2 C1 H1D 123.1 2_656 . ?
H1B C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
C2 C2 C3 84.7(13) 2_656 2_656 ?
C2 C2 C1 98.9(4) 2_656 . ?
C3 C2 C1 125.2(8) 2_656 . ?
C2 C2 C3 63.3(11) 2_656 . ?
C3 C2 C3 110.4(6) 2_656 . ?
C1 C2 C3 120.0(7) . . ?
C2 C2 C1 55.1(4) 2_656 2_656 ?
C3 C2 C1 110.1(7) 2_656 2_656 ?
C1 C2 C1 44.2(7) . 2_656 ?
C3 C2 C1 99.3(5) . 2_656 ?
C2 C3 C4 122.8(5) 2_656 . ?
C2 C3 C2 32.1(6) 2_656 . ?
C4 C3 C2 119.1(4) . . ?
C2 C3 H3A 107.8 2_656 . ?
C4 C3 H3A 120.0 . . ?
C2 C3 H3A 121.0 . . ?
C3 C4 C5 118.1(4) . . ?
C3 C4 P1 121.4(3) . . ?
C5 C4 P1 120.5(3) . . ?
C4 C5 C4 121.8(5) 2_656 . ?
C4 C5 H5A 119.1 2_656 . ?
C4 C5 H5A 119.1 . . ?
N1 C6 C7 122.9(6) . . ?
N1 C6 H6A 118.6 . . ?
C7 C6 H6A 118.6 . . ?
C6 C7 C8 120.6(6) . . ?
C6 C7 H7A 119.7 . . ?
C8 C7 H7A 119.7 . . ?
N1 C6' C7' 124.7(8) . . ?
N1 C6' H6'A 117.7 . . ?
C7' C6' H6'A 117.7 . . ?
C8 C7' C6' 119.2(7) . . ?
C8 C7' H7'A 120.4 . . ?
C6' C7' H7'A 120.4 . . ?
C7' C8 C7' 117.2(8) 2_757 . ?
C7 C8 C7 115.7(7) 2_757 . ?
C7' C8 C9 121.4(4) 2_757 . ?
C7' C8 C9 121.4(4) . . ?
C7 C8 C9 122.1(3) 2_757 . ?
C7 C8 C9 122.1(3) . . ?
C10 C9 C10 117.3(4) . 2_757 ?
C10 C9 C8 121.4(2) . . ?
C10 C9 C8 121.4(2) 2_757 . ?
C11 C10 C9 119.3(3) . . ?
C11 C10 H10A 120.3 . . ?
C9 C10 H10A 120.3 . . ?
N2 C11 C10 123.5(3) . . ?
N2 C11 H11A 118.3 . . ?
C10 C11 H11A 118.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O3 P1 O2 -73.2(2) . . . . ?
Cu1 O3 P1 O1 52.0(2) . . . . ?
Cu1 O3 P1 C4 166.4(2) . . . . ?
C1 C1 C2 C2 -6.7(17) 2_656 . . 2_656 ?
C1 C1 C2 C3 83.0(11) 2_656 . . 2_656 ?
C2 C1 C2 C3 89.8(18) 2_656 . . 2_656 ?
C1 C1 C2 C3 -71.0(11) 2_656 . . . ?
C2 C1 C2 C3 -64.2(12) 2_656 . . . ?
C2 C1 C2 C1 6.7(17) 2_656 . . 2_656 ?
C3 C2 C3 C2 -72.6(11) 2_656 . . 2_656 ?
C1 C2 C3 C2 84.9(7) . . . 2_656 ?
C1 C2 C3 C2 43.0(6) 2_656 . . 2_656 ?
C2 C2 C3 C4 106.3(8) 2_656 . . . ?
C3 C2 C3 C4 33.6(7) 2_656 . . . ?
C1 C2 C3 C4 -168.8(6) . . . . ?
C1 C2 C3 C4 149.3(5) 2_656 . . . ?
C2 C3 C4 C5 19.5(8) 2_656 . . . ?
C2 C3 C4 C5 -17.8(7) . . . . ?
C2 C3 C4 P1 -160.8(5) 2_656 . . . ?
C2 C3 C4 P1 161.9(5) . . . . ?
O3 P1 C4 C3 -45.1(4) . . . . ?
O2 P1 C4 C3 -170.4(4) . . . . ?
O1 P1 C4 C3 70.1(4) . . . . ?
O3 P1 C4 C5 134.6(2) . . . . ?
O2 P1 C4 C5 9.4(3) . . . . ?
O1 P1 C4 C5 -110.2(3) . . . . ?
C3 C4 C5 C4 0.3(3) . . . 2_656 ?
P1 C4 C5 C4 -179.4(3) . . . 2_656 ?
C6' N1 C6 C7 60.3(8) 2_757 . . . ?
C6' N1 C6 C7 -62.7(8) . . . . ?
C6 N1 C6 C7 0.0(6) 2_757 . . . ?
Cu1 N1 C6 C7 -180.0(6) . . . . ?
N1 C6 C7 C8 -0.1(11) . . . . ?
C6' N1 C6' C7' -0.3(8) 2_757 . . . ?
C6 N1 C6' C7' 63.7(10) . . . . ?
C6 N1 C6' C7' -61.8(10) 2_757 . . . ?
Cu1 N1 C6' C7' 179.7(8) . . . . ?
N1 C6' C7' C8 0.7(16) . . . . ?
C6' C7' C8 C7' -0.3(7) . . . 2_757 ?
C6' C7' C8 C7 60.1(9) . . . 2_757 ?
C6' C7' C8 C7 -63.5(9) . . . . ?
C6' C7' C8 C9 179.7(7) . . . . ?
C6 C7 C8 C7' -61.2(8) . . . 2_757 ?
C6 C7 C8 C7' 64.1(8) . . . . ?
C6 C7 C8 C7 0.0(5) . . . 2_757 ?
C6 C7 C8 C9 -180.0(5) . . . . ?
C7' C8 C9 C10 55.0(6) 2_757 . . . ?
C7' C8 C9 C10 -125.0(6) . . . . ?
C7 C8 C9 C10 -31.6(4) 2_757 . . . ?
C7 C8 C9 C10 148.4(4) . . . . ?
C7' C8 C9 C10 -125.0(6) 2_757 . . 2_757 ?
C7' C8 C9 C10 55.0(6) . . . 2_757 ?
C7 C8 C9 C10 148.4(4) 2_757 . . 2_757 ?
C7 C8 C9 C10 -31.6(4) . . . 2_757 ?
C10 C9 C10 C11 -0.1(3) 2_757 . . . ?
C8 C9 C10 C11 179.9(3) . . . . ?
C11 N2 C11 C10 -0.1(3) 2_757 . . . ?
Cu1 N2 C11 C10 179.9(3) 1_565 . . . ?
C9 C10 C11 N2 0.3(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O2 0.82 1.74 2.553(3) 173.3 3_657
O1W H2W O1 0.85 2.09 2.859(4) 151.0 2_757
O1W H1W O2 0.85 2.21 2.948(4) 145.5 3_757
C5 H5A O2 0.93 2.58 2.994(4) 107.3 .
C5 H5A O2 0.93 2.58 2.994(4) 107.3 2_656
C6 H6A O3 0.93 2.46 2.908(7) 109.8 2_757

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.079

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1452823'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 N2 O6 P2 Zn'
_chemical_formula_weight         471.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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'

_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                   8.6253(11)
_cell_length_b                   9.2656(12)
_cell_length_c                   12.1600(15)
_cell_angle_alpha                93.404(2)
_cell_angle_beta                 107.127(2)
_cell_angle_gamma                102.703(2)
_cell_volume                     897.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8538
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      27.52

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.744
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    1.586
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.690
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8534
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.273
_diffrn_reflns_theta_max         27.523
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4013
_reflns_number_gt                3117
_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 XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0353P)²+0.3536P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4013
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0887
_refine_ls_wR_factor_gt          0.0815
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
Zn1 Zn 0.67646(4) 0.64169(4) 0.88564(3) 0.02060(11) Uani 1 1 d . . . . .
O1 O 0.6651(3) 0.6169(2) 0.61947(18) 0.0281(5) Uani 1 1 d . . . . .
O2 O 0.5087(2) 0.3441(2) 0.57675(18) 0.0274(5) Uani 1 1 d . . . . .
H2B H 0.4727 0.3749 0.5148 0.041 Uiso 1 1 calc R U . . .
O3 O 0.6719(2) 0.4628(2) 0.78222(17) 0.0239(5) Uani 1 1 d . . . . .
O4 O 1.4237(2) 0.5743(2) 0.86120(18) 0.0249(5) Uani 1 1 d . . . . .
O5 O 1.4069(3) 0.2985(2) 0.83477(19) 0.0290(5) Uani 1 1 d . . . . .
H5A H 1.4870 0.3356 0.8136 0.043 Uiso 1 1 calc R U . . .
O6 O 1.2465(3) 0.3915(3) 0.95289(18) 0.0320(5) Uani 1 1 d . . . . .
N1 N 0.6482(3) 0.8339(3) 0.8100(2) 0.0229(6) Uani 1 1 d . . . . .
N2 N 0.9357(3) 0.7654(3) 0.9078(2) 0.0254(6) Uani 1 1 d . . . . .
P1 P 0.66068(9) 0.45971(9) 0.65456(7) 0.02037(18) Uani 1 1 d . . . . .
P2 P 1.31270(9) 0.42213(9) 0.85341(7) 0.02022(18) Uani 1 1 d . . . . .
C1 C 0.4987(4) 0.8579(4) 0.7584(3) 0.0335(8) Uani 1 1 d . . . . .
H1A H 0.4048 0.7982 0.7702 0.040 Uiso 1 1 calc R U . . .
C2 C 0.4782(5) 0.9678(4) 0.6882(4) 0.0487(10) Uani 1 1 d . . . . .
H2A H 0.3729 0.9848 0.6557 0.058 Uiso 1 1 calc R U . . .
C3 C 0.6148(5) 1.0515(4) 0.6668(4) 0.0484(11) Uani 1 1 d . . . . .
H3A H 0.6028 1.1228 0.6163 0.058 Uiso 1 1 calc R U . . .
C4 C 0.7709(4) 1.0296(4) 0.7207(3) 0.0373(8) Uani 1 1 d . . . . .
H4A H 0.8656 1.0874 0.7085 0.045 Uiso 1 1 calc R U . . .
C5 C 0.7845(4) 0.9206(3) 0.7931(3) 0.0247(7) Uani 1 1 d . . . . .
C6 C 0.9473(4) 0.8908(3) 0.8570(3) 0.0219(6) Uani 1 1 d . . . . .
C7 C 1.1004(4) 0.9860(4) 0.8672(3) 0.0332(8) Uani 1 1 d . . . . .
H7A H 1.1058 1.0730 0.8326 0.040 Uiso 1 1 calc R U . . .
C8 C 1.2449(4) 0.9495(4) 0.9296(3) 0.0390(9) Uani 1 1 d . . . . .
H8A H 1.3491 1.0120 0.9377 0.047 Uiso 1 1 calc R U . . .
C9 C 1.2341(4) 0.8210(4) 0.9794(3) 0.0390(9) Uani 1 1 d . . . . .
H9A H 1.3303 0.7932 1.0199 0.047 Uiso 1 1 calc R U . . .
C10 C 1.0771(4) 0.7330(4) 0.9684(3) 0.0330(8) Uani 1 1 d . . . . .
H10A H 1.0698 0.6474 1.0049 0.040 Uiso 1 1 calc R U . . .
C11 C 0.9750(4) 0.2100(4) 0.4117(3) 0.0403(9) Uani 1 1 d . . . . .
H11A H 0.8668 0.1993 0.3557 0.060 Uiso 1 1 calc R U . . .
H11B H 0.9943 0.1131 0.4235 0.060 Uiso 1 1 calc R U . . .
H11C H 1.0598 0.2664 0.3839 0.060 Uiso 1 1 calc R U . . .
C12 C 0.9813(4) 0.2902(3) 0.5248(3) 0.0252(7) Uani 1 1 d . . . . .
C13 C 1.1232(4) 0.3178(3) 0.6212(3) 0.0259(7) Uani 1 1 d . . . . .
H13A H 1.2172 0.2891 0.6145 0.031 Uiso 1 1 calc R U . . .
C14 C 1.1296(3) 0.3869(3) 0.7275(2) 0.0196(6) Uani 1 1 d . . . . .
C15 C 0.9880(4) 0.4302(3) 0.7364(2) 0.0216(6) Uani 1 1 d . . . . .
H15A H 0.9898 0.4755 0.8073 0.026 Uiso 1 1 calc R U . . .
C16 C 0.8442(3) 0.4065(3) 0.6408(2) 0.0198(6) Uani 1 1 d . . . . .
C17 C 0.8432(4) 0.3371(3) 0.5357(3) 0.0248(7) Uani 1 1 d . . . . .
H17A H 0.7480 0.3217 0.4712 0.030 Uiso 1 1 calc R U . . .


_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
Zn1 O6 1.945(2) 2_767 ?
Zn1 O3 2.006(2) . ?
Zn1 O4 2.057(2) 1_455 ?
Zn1 N1 2.081(2) . ?
Zn1 N2 2.206(3) . ?
O1 P1 1.537(2) . ?
O2 P1 1.514(2) . ?
O3 P1 1.525(2) . ?
O4 P2 1.500(2) . ?
O4 Zn1 2.057(2) 1_655 ?
O5 P2 1.585(2) . ?
O6 P2 1.499(2) . ?
O6 Zn1 1.945(2) 2_767 ?
N1 C1 1.331(4) . ?
N1 C5 1.348(4) . ?
N2 C10 1.334(4) . ?
N2 C6 1.346(4) . ?
P1 C16 1.807(3) . ?
P2 C14 1.798(3) . ?
C1 C2 1.376(5) . ?
C2 C3 1.363(5) . ?
C3 C4 1.378(5) . ?
C4 C5 1.381(4) . ?
C5 C6 1.485(4) . ?
C6 C7 1.384(4) . ?
C7 C8 1.380(5) . ?
C8 C9 1.365(5) . ?
C9 C10 1.382(4) . ?
C11 C12 1.505(4) . ?
C12 C13 1.386(4) . ?
C12 C17 1.392(4) . ?
C13 C14 1.389(4) . ?
C14 C15 1.397(4) . ?
C15 C16 1.393(4) . ?
C16 C17 1.393(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Zn1 O3 109.55(9) 2_767 . ?
O6 Zn1 O4 97.33(9) 2_767 1_455 ?
O3 Zn1 O4 92.68(8) . 1_455 ?
O6 Zn1 N1 131.75(10) 2_767 . ?
O3 Zn1 N1 117.36(9) . . ?
O4 Zn1 N1 91.34(9) 1_455 . ?
O6 Zn1 N2 87.70(9) 2_767 . ?
O3 Zn1 N2 97.25(9) . . ?
O4 Zn1 N2 166.69(9) 1_455 . ?
N1 Zn1 N2 76.24(10) . . ?
P1 O3 Zn1 125.08(12) . . ?
P2 O4 Zn1 130.76(12) . 1_655 ?
P2 O6 Zn1 140.01(13) . 2_767 ?
C1 N1 C5 118.8(3) . . ?
C1 N1 Zn1 122.5(2) . . ?
C5 N1 Zn1 117.3(2) . . ?
C10 N2 C6 118.2(3) . . ?
C10 N2 Zn1 127.6(2) . . ?
C6 N2 Zn1 114.1(2) . . ?
O2 P1 O3 112.08(12) . . ?
O2 P1 O1 112.14(12) . . ?
O3 P1 O1 109.64(12) . . ?
O2 P1 C16 107.44(13) . . ?
O3 P1 C16 106.73(12) . . ?
O1 P1 C16 108.58(13) . . ?
O6 P2 O4 116.97(13) . . ?
O6 P2 O5 108.55(13) . . ?
O4 P2 O5 109.76(12) . . ?
O6 P2 C14 104.91(12) . . ?
O4 P2 C14 110.67(13) . . ?
O5 P2 C14 105.26(13) . . ?
N1 C1 C2 122.4(3) . . ?
C3 C2 C1 118.9(3) . . ?
C2 C3 C4 119.4(3) . . ?
C3 C4 C5 119.0(3) . . ?
N1 C5 C4 121.3(3) . . ?
N1 C5 C6 115.7(3) . . ?
C4 C5 C6 123.0(3) . . ?
N2 C6 C7 121.9(3) . . ?
N2 C6 C5 115.0(3) . . ?
C7 C6 C5 123.1(3) . . ?
C8 C7 C6 118.8(3) . . ?
C9 C8 C7 119.6(3) . . ?
C8 C9 C10 118.6(3) . . ?
N2 C10 C9 122.8(3) . . ?
C13 C12 C17 118.2(3) . . ?
C13 C12 C11 121.1(3) . . ?
C17 C12 C11 120.7(3) . . ?
C12 C13 C14 122.0(3) . . ?
C13 C14 C15 118.5(3) . . ?
C13 C14 P2 122.4(2) . . ?
C15 C14 P2 119.1(2) . . ?
C16 C15 C14 121.0(3) . . ?
C15 C16 C17 118.7(3) . . ?
C15 C16 P1 120.4(2) . . ?
C17 C16 P1 120.8(2) . . ?
C12 C17 C16 121.5(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 H2B O1 0.82 1.73 2.511(3) 158.3 2_666
O5 H5A O3 0.82 1.91 2.719(3) 167.1 1_655
C1 H1A O4 0.93 2.42 3.001(4) 120.3 1_455
C13 H13A O5 0.93 2.68 3.044(4) 104.1 .
C15 H15A O3 0.93 2.64 3.012(3) 104.4 .
C15 H15A O6 0.93 2.69 3.005(3) 100.5 .
C17 H17A O2 0.93 2.77 3.083(4) 100.9 .

_refine_diff_density_max         0.436
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.084

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1452824'
_audit_update_record             
;
2016-03-09 deposited with the CCDC.
2016-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H30 Cd N2 O13 P2'
_chemical_formula_weight         644.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   14.3240(17)
_cell_length_b                   21.707(2)
_cell_length_c                   16.2613(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5056.1(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    24429
_cell_measurement_theta_min      1.88
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_F_000             2624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    1.056
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.745
_exptl_absorpt_correction_T_max  0.854
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19301
_diffrn_reflns_av_unetI/netI     0.0925
_diffrn_reflns_av_R_equivalents  0.1044
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.876
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             4424
_reflns_number_gt                2286
_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 XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_vrf_PLAT230_6                   
;
PROBLEM: Hirshfeld Test Diff for  P1 --  O1.
RESPONSE: This could be caused by the poor quality of the crystal.
;
_vrf_PLAT417_6                   
;
PROBLEM: Short Inter D-H..H-D H1W  ..  H4W.
RESPONSE: This could be caused by the poor quality of the crystal.
;
_vrf_PLAT420_6                   
;
PROBLEM: D-H Without Acceptor O1W    --  H2W.
RESPONSE: This could be caused by the poor quality of the crystal.
;
_vrf_PLAT482_6                   
;
PROBLEM: Small D-H..A Angle Rep for O2W  ..  O4 .
RESPONSE: This could be caused by the poor quality of the crystal.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0584P)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         4424
_refine_ls_number_parameters     317
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1308
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1175
_refine_ls_wR_factor_gt          0.0975
_refine_ls_goodness_of_fit_ref   0.885
_refine_ls_restrained_S_all      0.888
_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
Cd1 Cd 0.58552(3) 0.04760(2) 0.05345(3) 0.02531(15) Uani 1 1 d . . . . .
O1W O 0.5803(3) 0.12877(18) -0.0364(2) 0.0357(11) Uani 1 1 d . . . . .
H1W H 0.6172 0.1559 -0.0555 0.043 Uiso 1 1 d R U . . .
H2W H 0.5300 0.1165 -0.0588 0.043 Uiso 1 1 d R U . . .
O1 O 0.7532(2) 0.05925(15) 0.4549(2) 0.0174(9) Uani 1 1 d . U . . .
H1A H 0.7596 0.0379 0.4961 0.026 Uiso 1 1 calc R U . . .
O2 O 0.8660(3) 0.14058(18) 0.4083(3) 0.0337(11) Uani 1 1 d . . . . .
O2W O 0.7292(3) 0.2059(2) -0.0464(3) 0.0520(14) Uani 1 1 d . . . . .
H3W H 0.7599 0.2162 -0.0890 0.062 Uiso 1 1 d R U . . .
H4W H 0.6942 0.2150 -0.0061 0.062 Uiso 1 1 d R U . . .
O3 O 0.9250(3) 0.03831(16) 0.4657(2) 0.0213(10) Uani 1 1 d . . . . .
O3W O 0.9387(3) 0.2136(2) 0.5243(3) 0.0512(14) Uani 1 1 d . . . . .
H5W H 0.8992 0.2362 0.5491 0.061 Uiso 1 1 d R U . . .
H6W H 0.9926 0.2090 0.5454 0.061 Uiso 1 1 d R U . . .
O4 O 0.8048(3) 0.14562(19) 0.0837(3) 0.0388(12) Uani 1 1 d . . . . .
O4W O 0.9984(4) 0.1663(2) -0.0268(3) 0.0638(16) Uani 1 1 d . . . . .
H7W H 0.9709 0.1800 -0.0694 0.077 Uiso 1 1 d R U . . .
H8W H 1.0577 0.1665 -0.0263 0.077 Uiso 1 1 d R U . . .
O5 O 0.9117(3) 0.0663(2) 0.0228(3) 0.0394(11) Uani 1 1 d . . . . .
H5A H 0.9372 0.0993 0.0124 0.059 Uiso 1 1 calc R U . . .
O5W O 0.6899(4) 0.1814(2) 0.5297(3) 0.0606(16) Uani 1 1 d . . . . .
H9W H 0.7375 0.1585 0.5226 0.073 Uiso 1 1 d R U . . .
H10W H 0.6806 0.1906 0.4795 0.073 Uiso 1 1 d R U . . .
O6 O 0.7427(3) 0.04560(18) 0.0249(2) 0.0295(10) Uani 1 1 d . . . . .
O6W O 0.8103(4) 0.2545(2) 0.1526(3) 0.0572(15) Uani 1 1 d . . . . .
H11W H 0.8689 0.2522 0.1602 0.069 Uiso 1 1 d R U . . .
H12W H 0.7792 0.2809 0.1253 0.069 Uiso 1 1 d R U . . .
O7W O 0.8301(4) 0.2493(2) 0.3277(3) 0.0677(17) Uani 1 1 d . . . . .
H13W H 0.8010 0.2393 0.2841 0.081 Uiso 1 1 d R U . . .
H14W H 0.8887 0.2503 0.3359 0.081 Uiso 1 1 d R U . . .
N1 N 0.5929(4) -0.0135(2) 0.1695(3) 0.0291(12) Uani 1 1 d . . . . .
N2 N 0.5825(4) 0.1099(2) 0.1703(3) 0.0320(13) Uani 1 1 d . . . . .
P1 P 0.85204(12) 0.07302(8) 0.41591(10) 0.0230(4) Uani 1 1 d . . . . .
P2 P 0.81941(12) 0.07854(8) 0.07179(10) 0.0252(4) Uani 1 1 d . . . . .
C1 C 0.8528(5) -0.1280(3) 0.2371(4) 0.050(2) Uani 1 1 d . . . . .
H1B H 0.8637 -0.1421 0.1819 0.075 Uiso 1 1 calc R U . . .
H1C H 0.7949 -0.1446 0.2568 0.075 Uiso 1 1 calc R U . . .
H1D H 0.9029 -0.1414 0.2720 0.075 Uiso 1 1 calc R U . . .
C2 C 0.8480(5) -0.0590(3) 0.2377(4) 0.0312(17) Uani 1 1 d . . . . .
C3 C 0.8518(4) -0.0276(3) 0.3119(4) 0.0263(16) Uani 1 1 d . . . . .
H3A H 0.8580 -0.0499 0.3604 0.032 Uiso 1 1 calc R U . . .
C4 C 0.8467(4) 0.0371(3) 0.3158(4) 0.0232(15) Uani 1 1 d . . . . .
C5 C 0.8375(4) 0.0700(3) 0.2422(4) 0.0226(14) Uani 1 1 d . . . . .
H5B H 0.8338 0.1128 0.2435 0.027 Uiso 1 1 calc R U . . .
C6 C 0.8339(4) 0.0396(3) 0.1677(4) 0.0238(15) Uani 1 1 d . . . . .
C7 C 0.8401(4) -0.0249(3) 0.1673(4) 0.0319(17) Uani 1 1 d . . . . .
H7A H 0.8388 -0.0453 0.1170 0.038 Uiso 1 1 calc R U . . .
C8 C 0.5982(5) -0.0754(3) 0.1654(4) 0.0352(17) Uani 1 1 d . . . . .
H8A H 0.6003 -0.0943 0.1141 0.042 Uiso 1 1 calc R U . . .
C9 C 0.6005(5) -0.1112(3) 0.2341(5) 0.047(2) Uani 1 1 d . . . . .
H9A H 0.6026 -0.1538 0.2294 0.057 Uiso 1 1 calc R U . . .
C10 C 0.5997(5) -0.0842(3) 0.3096(5) 0.052(2) Uani 1 1 d . . . . .
H10A H 0.6020 -0.1081 0.3571 0.063 Uiso 1 1 calc R U . . .
C11 C 0.5956(5) -0.0209(3) 0.3144(4) 0.0419(18) Uani 1 1 d . . . . .
H11A H 0.5955 -0.0016 0.3654 0.050 Uiso 1 1 calc R U . . .
C12 C 0.5916(5) 0.0139(3) 0.2430(4) 0.0293(15) Uani 1 1 d . . . . .
C13 C 0.5863(5) 0.0822(3) 0.2440(4) 0.0308(15) Uani 1 1 d . . . . .
C14 C 0.5832(6) 0.1156(3) 0.3161(5) 0.051(2) Uani 1 1 d . . . . .
H14A H 0.5857 0.0959 0.3668 0.061 Uiso 1 1 calc R U . . .
C15 C 0.5765(6) 0.1789(4) 0.3112(5) 0.065(3) Uani 1 1 d . . . . .
H15A H 0.5753 0.2024 0.3591 0.078 Uiso 1 1 calc R U . . .
C16 C 0.5714(6) 0.2071(4) 0.2365(5) 0.061(2) Uani 1 1 d . . . . .
H16A H 0.5652 0.2496 0.2325 0.073 Uiso 1 1 calc R U . . .
C17 C 0.5757(5) 0.1713(3) 0.1677(5) 0.050(2) Uani 1 1 d . . . . .
H17A H 0.5739 0.1904 0.1166 0.060 Uiso 1 1 calc R U . . .


_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
Cd1 O1W 2.290(4) . ?
Cd1 O6 2.300(4) . ?
Cd1 N1 2.309(5) . ?
Cd1 O3 2.329(4) 6_556 ?
Cd1 N2 2.333(5) . ?
Cd1 O3 2.353(3) 2_654 ?
O1 P1 1.580(4) . ?
O2 P1 1.485(4) . ?
O3 P1 1.521(4) . ?
O3 Cd1 2.329(4) 6_656 ?
O3 Cd1 2.353(3) 2_655 ?
O4 P2 1.484(4) . ?
O5 P2 1.566(5) . ?
O6 P2 1.516(4) . ?
N1 C12 1.336(7) . ?
N1 C8 1.348(7) . ?
N2 C17 1.336(7) . ?
N2 C13 1.341(8) . ?
P1 C4 1.807(6) . ?
P2 C6 1.787(6) . ?
C1 C2 1.500(8) . ?
C2 C7 1.369(8) . ?
C2 C3 1.385(8) . ?
C3 C4 1.407(8) . ?
C4 C5 1.400(8) . ?
C5 C6 1.380(8) . ?
C6 C7 1.401(8) . ?
C8 C9 1.360(9) . ?
C9 C10 1.360(9) . ?
C10 C11 1.378(9) . ?
C11 C12 1.386(9) . ?
C12 C13 1.484(8) . ?
C13 C14 1.379(9) . ?
C14 C15 1.380(10) . ?
C15 C16 1.363(10) . ?
C16 C17 1.364(9) . ?

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
O1W Cd1 O6 85.26(15) . . ?
O1W Cd1 N1 164.75(16) . . ?
O6 Cd1 N1 96.29(17) . . ?
O1W Cd1 O3 87.11(14) . 6_556 ?
O6 Cd1 O3 159.74(13) . 6_556 ?
N1 Cd1 O3 95.99(16) . 6_556 ?
O1W Cd1 N2 94.19(16) . . ?
O6 Cd1 N2 101.17(17) . . ?
N1 Cd1 N2 70.61(17) . . ?
O3 Cd1 N2 98.07(16) 6_556 . ?
O1W Cd1 O3 102.75(13) . 2_654 ?
O6 Cd1 O3 85.71(14) . 2_654 ?
N1 Cd1 O3 92.50(15) . 2_654 ?
O3 Cd1 O3 77.72(14) 6_556 2_654 ?
N2 Cd1 O3 162.24(15) . 2_654 ?
P1 O3 Cd1 124.4(2) . 6_656 ?
P1 O3 Cd1 132.2(2) . 2_655 ?
Cd1 O3 Cd1 102.28(14) 6_656 2_655 ?
P2 O6 Cd1 126.8(2) . . ?
C12 N1 C8 119.3(6) . . ?
C12 N1 Cd1 118.4(4) . . ?
C8 N1 Cd1 122.4(4) . . ?
C17 N2 C13 118.6(6) . . ?
C17 N2 Cd1 123.6(5) . . ?
C13 N2 Cd1 117.8(4) . . ?
O2 P1 O3 116.2(2) . . ?
O2 P1 O1 109.9(2) . . ?
O3 P1 O1 108.0(2) . . ?
O2 P1 C4 110.9(3) . . ?
O3 P1 C4 107.1(2) . . ?
O1 P1 C4 104.0(2) . . ?
O4 P2 O6 115.2(3) . . ?
O4 P2 O5 110.6(3) . . ?
O6 P2 O5 106.0(2) . . ?
O4 P2 C6 111.5(3) . . ?
O6 P2 C6 107.5(3) . . ?
O5 P2 C6 105.4(3) . . ?
C7 C2 C3 117.8(5) . . ?
C7 C2 C1 122.5(6) . . ?
C3 C2 C1 119.7(6) . . ?
C2 C3 C4 121.8(6) . . ?
C5 C4 C3 118.4(5) . . ?
C5 C4 P1 123.6(5) . . ?
C3 C4 P1 118.0(5) . . ?
C6 C5 C4 120.6(5) . . ?
C5 C6 C7 118.7(6) . . ?
C5 C6 P2 122.9(5) . . ?
C7 C6 P2 118.4(5) . . ?
C2 C7 C6 122.7(6) . . ?
N1 C8 C9 122.0(7) . . ?
C10 C9 C8 119.7(7) . . ?
C9 C10 C11 118.7(7) . . ?
C10 C11 C12 119.9(7) . . ?
N1 C12 C11 120.4(6) . . ?
N1 C12 C13 117.0(6) . . ?
C11 C12 C13 122.6(6) . . ?
N2 C13 C14 121.5(6) . . ?
N2 C13 C12 116.2(6) . . ?
C14 C13 C12 122.3(6) . . ?
C13 C14 C15 118.5(7) . . ?
C16 C15 C14 120.1(7) . . ?
C15 C16 C17 118.2(7) . . ?
N2 C17 C16 123.1(7) . . ?

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
O1W H1W O2W 0.85 1.94 2.716(6) 150.7 .
O1W H2W O3W 0.85 2.54 2.747(6) 94.7 6_556
O2W H4W O1W 0.85 2.53 2.716(6) 93.3 .
O2W H4W O4 0.85 2.63 2.713(6) 86.5 .
O2W H4W O5W 0.85 2.32 2.800(7) 115.7 7_565
O2W H3W O7W 0.85 1.85 2.688(7) 170.5 7_565
O3W H6W O1W 0.85 2.15 2.747(6) 126.7 6_656
O3W H5W O6W 0.85 2.12 2.866(7) 146.2 7_566
O4W H7W O3W 0.85 2.81 2.865(7) 85.4 7_565
O4W H8W O5W 0.85 1.92 2.763(7) 170.4 6_656
O5W H9W O1 0.85 2.43 3.054(6) 130.7 .
O5W H10W O2W 0.85 2.39 2.800(7) 110.2 7_566
O6W H11W O3W 0.85 2.54 2.866(7) 104.2 7_565
O6W H12W O5W 0.85 2.17 2.985(7) 159.4 7_565
O6W H11W O7W 0.85 2.78 2.863(7) 86.9 .
O7W H14W O2 0.85 2.68 2.748(6) 85.8 .
O7W H13W O6W 0.85 2.17 2.863(7) 138.9 .
O1 H1A O6 0.82 1.87 2.545(5) 138.5 2_655
O5 H5A O4W 0.82 1.82 2.628(6) 170.6 .


_refine_diff_density_max         1.372
_refine_diff_density_min         -0.739
_refine_diff_density_rms         0.128

_shelxl_version_number           2013-2

