# Electronic Supplementary Material (ESI) for ChemComm.
# 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 1823683'
_audit_update_record             
;
2018-04-05 deposited with the CCDC.
2018-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 Cu3 O15 P2'
_chemical_formula_sum            'C14 H18 Cu3 O15 P2'
_chemical_formula_weight         678.84

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

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

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

_cell_length_a                   8.872(2)
_cell_length_b                   9.054(3)
_cell_length_c                   13.255(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.344(6)
_cell_angle_gamma                90
_cell_volume                     1040.2(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3189
_cell_measurement_theta_min      2.3497
_cell_measurement_theta_max      27.4642

_exptl_crystal_description       sheet-like
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.167
_exptl_crystal_F_000             678
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    3.272
_shelx_estimated_absorpt_T_min   0.736
_shelx_estimated_absorpt_T_max   0.880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.740
_exptl_absorpt_correction_T_max  0.877
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_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 APEX II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8292
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.745
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4645
_reflns_number_gt                3838
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.881
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0165P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.010(14)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4645
_refine_ls_number_parameters     310
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0565
_refine_ls_wR_factor_gt          0.0549
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      0.999
_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 0.17378(5) 0.87391(9) 0.53897(4) 0.01081(12) Uani 1 1 d . . . . .
Cu2 Cu 0.48661(5) 0.37017(9) 0.69894(4) 0.00953(12) Uani 1 1 d . . . . .
Cu3 Cu 0.75655(5) -0.13031(9) 0.67488(4) 0.01029(12) Uani 1 1 d . . . . .
P1 P 0.44207(13) 0.71171(14) 0.69047(10) 0.0098(3) Uani 1 1 d . . . . .
P2 P 0.80013(14) 0.21419(14) 0.66877(10) 0.0104(3) Uani 1 1 d . . . . .
C1 C 0.4086(5) 0.6960(6) 0.8199(4) 0.0121(11) Uani 1 1 d . . . . .
C2 C 0.4917(6) 0.7807(6) 0.9005(4) 0.0157(12) Uani 1 1 d . . . . .
H2A H 0.5624 0.8501 0.8875 0.019 Uiso 1 1 calc R U . . .
C3 C 0.4697(6) 0.7622(7) 1.0009(4) 0.0221(13) Uani 1 1 d . . . . .
H3A H 0.5281 0.8162 1.0551 0.027 Uiso 1 1 calc R U . . .
C4 C 0.3602(6) 0.6629(7) 1.0190(4) 0.0191(12) Uani 1 1 d . . . . .
H4A H 0.3449 0.6507 1.0857 0.023 Uiso 1 1 calc R U . . .
C5 C 0.2739(6) 0.5819(6) 0.9396(4) 0.0176(12) Uani 1 1 d . . . . .
H5A H 0.1981 0.5180 0.9525 0.021 Uiso 1 1 calc R U . . .
C6 C 0.2996(5) 0.5953(5) 0.8401(4) 0.0100(10) Uani 1 1 d . . . . .
C7 C 0.2060(5) 0.4995(5) 0.7554(4) 0.0098(10) Uani 1 1 d . . . . .
C8 C 0.9442(5) 0.1853(5) 0.7878(4) 0.0108(10) Uani 1 1 d . . . . .
C9 C 0.9393(6) 0.2675(6) 0.8746(4) 0.0155(11) Uani 1 1 d . . . . .
H9A H 0.8683 0.3441 0.8699 0.019 Uiso 1 1 calc R U . . .
C10 C 1.0385(6) 0.2384(6) 0.9692(4) 0.0209(12) Uani 1 1 d . . . . .
H10A H 1.0302 0.2920 1.0276 0.025 Uiso 1 1 calc R U . . .
C11 C 1.1491(6) 0.1295(6) 0.9756(4) 0.0204(13) Uani 1 1 d . . . . .
H11A H 1.2156 0.1096 1.0384 0.025 Uiso 1 1 calc R U . . .
C12 C 1.1612(5) 0.0498(6) 0.8881(4) 0.0163(11) Uani 1 1 d . . . . .
H12A H 1.2378 -0.0213 0.8919 0.020 Uiso 1 1 calc R U . . .
C13 C 1.0583(5) 0.0767(5) 0.7948(4) 0.0100(10) Uani 1 1 d . . . . .
C14 C 1.0742(5) -0.0146(5) 0.7024(4) 0.0122(11) Uani 1 1 d . . . . .
O1 O 0.2880(4) 0.7168(4) 0.6154(3) 0.0128(7) Uani 1 1 d . . . . .
O2 O 0.5438(3) 0.8462(4) 0.6867(3) 0.0138(9) Uani 1 1 d . . . . .
O3 O 0.5322(4) 0.5711(4) 0.6746(3) 0.0136(8) Uani 1 1 d . . . . .
O4 O 0.2759(3) 0.4048(4) 0.7112(3) 0.0136(8) Uani 1 1 d . . . . .
O5 O 0.0645(3) 0.5168(4) 0.7321(3) 0.0125(7) Uani 1 1 d . . . . .
O6 O 0.6996(3) 0.3431(4) 0.6892(3) 0.0144(9) Uani 1 1 d . . . . .
O7 O 0.7024(4) 0.0736(4) 0.6523(3) 0.0137(8) Uani 1 1 d . . . . .
O8 O 0.8840(4) 0.2439(4) 0.5817(3) 0.0121(7) Uani 1 1 d . . . . .
O9 O 0.9685(3) -0.1022(4) 0.6605(3) 0.0148(9) Uani 1 1 d . . . . .
O10 O 1.1961(4) -0.0032(4) 0.6696(3) 0.0124(8) Uani 1 1 d . . . . .
O1W O 0.3766(4) 1.0125(4) 0.5124(2) 0.0159(8) Uani 1 1 d . . . . .
H1WA H 0.4605 0.9679 0.5375 0.024 Uiso 1 1 d R U . . .
H1WB H 0.3688 1.0250 0.4479 0.024 Uiso 1 1 d R U . . .
O2W O 0.0258(4) 1.0212(5) 0.4705(3) 0.0345(11) Uani 1 1 d . . . . .
H2WA H 0.0362 1.0319 0.4086 0.052 Uiso 1 1 d R U . . .
H2WB H 0.0434 1.1029 0.5023 0.052 Uiso 1 1 d R U . . .
O3W O 0.4621(4) 0.1643(4) 0.7333(3) 0.0117(7) Uani 1 1 d . . . . .
H3WA H 0.3707 0.1505 0.7413 0.018 Uiso 1 1 d R U . . .
H3WB H 0.4785 0.1099 0.6845 0.018 Uiso 1 1 d R U . . .
O4W O 0.6873(4) -0.1868(4) 0.4946(3) 0.0190(8) Uani 1 1 d . . . . .
H4WA H 0.7339 -0.1390 0.4552 0.12(4) Uiso 1 1 d R . . . .
H4WB H 0.6889 -0.2793 0.4839 0.021(16) Uiso 1 1 d R . . . .
O5W O 0.8184(4) -0.3197(4) 0.7437(3) 0.0159(8) Uani 1 1 d . . . . .
H5WA H 0.8944 -0.3549 0.7219 0.024 Uiso 1 1 d R U . . .
H5WB H 0.7431 -0.3797 0.7301 0.024 Uiso 1 1 d 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 O1 1.907(3) . ?
Cu1 O2W 1.954(4) . ?
Cu1 O8 1.963(3) 2_656 ?
Cu1 O10 2.033(3) 1_465 ?
Cu1 O1W 2.282(4) . ?
Cu2 O3 1.906(3) . ?
Cu2 O4 1.936(3) . ?
Cu2 O6 1.937(3) . ?
Cu2 O3W 1.942(3) . ?
Cu3 O7 1.915(3) . ?
Cu3 O2 1.939(3) 1_545 ?
Cu3 O9 1.947(3) . ?
Cu3 O5W 1.965(3) . ?
Cu3 O4W 2.393(4) . ?
P1 O1 1.510(3) . ?
P1 O2 1.523(4) . ?
P1 O3 1.542(4) . ?
P1 C1 1.808(5) . ?
P2 O8 1.525(4) . ?
P2 O6 1.528(3) . ?
P2 O7 1.529(3) . ?
P2 C8 1.824(5) . ?
C1 C2 1.392(7) . ?
C1 C6 1.396(7) . ?
C2 C3 1.395(8) . ?
C2 H2A 0.9300 . ?
C3 C4 1.381(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.373(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.392(7) . ?
C5 H5A 0.9300 . ?
C6 C7 1.518(6) . ?
C7 O5 1.237(5) . ?
C7 O4 1.273(6) . ?
C8 C9 1.379(7) . ?
C8 C13 1.400(7) . ?
C9 C10 1.395(7) . ?
C9 H9A 0.9300 . ?
C10 C11 1.381(8) . ?
C10 H10A 0.9300 . ?
C11 C12 1.389(7) . ?
C11 H11A 0.9300 . ?
C12 C13 1.393(7) . ?
C12 H12A 0.9300 . ?
C13 C14 1.510(7) . ?
C14 O10 1.252(6) . ?
C14 O9 1.263(6) . ?
O2 Cu3 1.939(3) 1_565 ?
O8 Cu1 1.963(3) 2_646 ?
O10 Cu1 2.033(3) 1_645 ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8500 . ?
O2W H2WA 0.8500 . ?
O2W H2WB 0.8500 . ?
O3W H3WA 0.8500 . ?
O3W H3WB 0.8501 . ?
O4W H4WA 0.8499 . ?
O4W H4WB 0.8499 . ?
O5W H5WA 0.8500 . ?
O5W H5WB 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
O1 Cu1 O2W 169.70(17) . . ?
O1 Cu1 O8 90.14(15) . 2_656 ?
O2W Cu1 O8 89.89(15) . 2_656 ?
O1 Cu1 O10 90.67(14) . 1_465 ?
O2W Cu1 O10 87.46(15) . 1_465 ?
O8 Cu1 O10 169.49(14) 2_656 1_465 ?
O1 Cu1 O1W 98.35(13) . . ?
O2W Cu1 O1W 91.53(17) . . ?
O8 Cu1 O1W 106.33(13) 2_656 . ?
O10 Cu1 O1W 83.92(13) 1_465 . ?
O3 Cu2 O4 95.93(14) . . ?
O3 Cu2 O6 82.20(14) . . ?
O4 Cu2 O6 177.74(15) . . ?
O3 Cu2 O3W 173.84(14) . . ?
O4 Cu2 O3W 88.70(14) . . ?
O6 Cu2 O3W 93.08(14) . . ?
O7 Cu3 O2 84.39(14) . 1_545 ?
O7 Cu3 O9 94.26(15) . . ?
O2 Cu3 O9 178.45(16) 1_545 . ?
O7 Cu3 O5W 161.77(15) . . ?
O2 Cu3 O5W 92.69(15) 1_545 . ?
O9 Cu3 O5W 88.82(14) . . ?
O7 Cu3 O4W 92.75(14) . . ?
O2 Cu3 O4W 90.62(13) 1_545 . ?
O9 Cu3 O4W 88.69(13) . . ?
O5W Cu3 O4W 105.29(14) . . ?
O1 P1 O2 114.4(2) . . ?
O1 P1 O3 111.0(2) . . ?
O2 P1 O3 109.12(18) . . ?
O1 P1 C1 108.6(2) . . ?
O2 P1 C1 108.2(2) . . ?
O3 P1 C1 105.0(2) . . ?
O8 P2 O6 113.40(19) . . ?
O8 P2 O7 113.1(2) . . ?
O6 P2 O7 109.02(19) . . ?
O8 P2 C8 108.3(2) . . ?
O6 P2 C8 106.5(2) . . ?
O7 P2 C8 106.0(2) . . ?
C2 C1 C6 119.2(5) . . ?
C2 C1 P1 121.2(4) . . ?
C6 C1 P1 119.6(4) . . ?
C1 C2 C3 120.5(5) . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 H2A 119.8 . . ?
C4 C3 C2 119.4(5) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C5 C4 C3 120.8(5) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 120.1(5) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C5 C6 C1 119.9(5) . . ?
C5 C6 C7 118.5(5) . . ?
C1 C6 C7 121.6(4) . . ?
O5 C7 O4 122.6(4) . . ?
O5 C7 C6 118.6(4) . . ?
O4 C7 C6 118.8(4) . . ?
C9 C8 C13 118.3(5) . . ?
C9 C8 P2 120.2(4) . . ?
C13 C8 P2 121.4(4) . . ?
C8 C9 C10 121.5(5) . . ?
C8 C9 H9A 119.3 . . ?
C10 C9 H9A 119.3 . . ?
C11 C10 C9 119.6(5) . . ?
C11 C10 H10A 120.2 . . ?
C9 C10 H10A 120.2 . . ?
C10 C11 C12 120.0(5) . . ?
C10 C11 H11A 120.0 . . ?
C12 C11 H11A 120.0 . . ?
C11 C12 C13 119.8(5) . . ?
C11 C12 H12A 120.1 . . ?
C13 C12 H12A 120.1 . . ?
C12 C13 C8 120.6(5) . . ?
C12 C13 C14 117.9(4) . . ?
C8 C13 C14 121.5(4) . . ?
O10 C14 O9 121.0(5) . . ?
O10 C14 C13 118.3(4) . . ?
O9 C14 C13 120.7(4) . . ?
P1 O1 Cu1 132.6(2) . . ?
P1 O2 Cu3 133.2(2) . 1_565 ?
P1 O3 Cu2 129.1(2) . . ?
C7 O4 Cu2 136.2(3) . . ?
P2 O6 Cu2 136.3(2) . . ?
P2 O7 Cu3 131.6(2) . . ?
P2 O8 Cu1 129.6(2) . 2_646 ?
C14 O9 Cu3 132.9(3) . . ?
C14 O10 Cu1 108.4(3) . 1_645 ?
Cu1 O1W H1WA 109.4 . . ?
Cu1 O1W H1WB 109.3 . . ?
H1WA O1W H1WB 109.5 . . ?
Cu1 O2W H2WA 109.0 . . ?
Cu1 O2W H2WB 109.2 . . ?
H2WA O2W H2WB 109.5 . . ?
Cu2 O3W H3WA 109.2 . . ?
Cu2 O3W H3WB 109.3 . . ?
H3WA O3W H3WB 109.5 . . ?
Cu3 O4W H4WA 116.7 . . ?
Cu3 O4W H4WB 111.5 . . ?
H4WA O4W H4WB 111.9 . . ?
Cu3 O5W H5WA 109.4 . . ?
Cu3 O5W H5WB 109.3 . . ?
H5WA O5W H5WB 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 P1 C1 C2 -135.7(4) . . . . ?
O2 P1 C1 C2 -11.0(5) . . . . ?
O3 P1 C1 C2 105.5(4) . . . . ?
O1 P1 C1 C6 45.5(5) . . . . ?
O2 P1 C1 C6 170.2(4) . . . . ?
O3 P1 C1 C6 -73.4(4) . . . . ?
C6 C1 C2 C3 1.9(7) . . . . ?
P1 C1 C2 C3 -177.0(4) . . . . ?
C1 C2 C3 C4 -2.4(8) . . . . ?
C2 C3 C4 C5 0.3(8) . . . . ?
C3 C4 C5 C6 2.3(8) . . . . ?
C4 C5 C6 C1 -2.8(7) . . . . ?
C4 C5 C6 C7 177.7(5) . . . . ?
C2 C1 C6 C5 0.7(7) . . . . ?
P1 C1 C6 C5 179.6(4) . . . . ?
C2 C1 C6 C7 -179.7(4) . . . . ?
P1 C1 C6 C7 -0.9(6) . . . . ?
C5 C6 C7 O5 63.6(6) . . . . ?
C1 C6 C7 O5 -115.9(5) . . . . ?
C5 C6 C7 O4 -116.5(5) . . . . ?
C1 C6 C7 O4 64.0(6) . . . . ?
O8 P2 C8 C9 126.3(4) . . . . ?
O6 P2 C8 C9 3.9(5) . . . . ?
O7 P2 C8 C9 -112.1(4) . . . . ?
O8 P2 C8 C13 -56.0(5) . . . . ?
O6 P2 C8 C13 -178.3(4) . . . . ?
O7 P2 C8 C13 65.7(5) . . . . ?
C13 C8 C9 C10 -4.0(8) . . . . ?
P2 C8 C9 C10 173.8(4) . . . . ?
C8 C9 C10 C11 3.1(8) . . . . ?
C9 C10 C11 C12 0.0(8) . . . . ?
C10 C11 C12 C13 -2.1(8) . . . . ?
C11 C12 C13 C8 1.1(8) . . . . ?
C11 C12 C13 C14 -178.9(5) . . . . ?
C9 C8 C13 C12 1.9(7) . . . . ?
P2 C8 C13 C12 -175.9(4) . . . . ?
C9 C8 C13 C14 -178.1(5) . . . . ?
P2 C8 C13 C14 4.1(7) . . . . ?
C12 C13 C14 O10 -63.3(6) . . . . ?
C8 C13 C14 O10 116.7(5) . . . . ?
C12 C13 C14 O9 115.3(5) . . . . ?
C8 C13 C14 O9 -64.7(7) . . . . ?
O2 P1 O1 Cu1 -16.8(4) . . . . ?
O3 P1 O1 Cu1 -140.9(3) . . . . ?
C1 P1 O1 Cu1 104.2(3) . . . . ?
O1 P1 O2 Cu3 -129.3(3) . . . 1_565 ?
O3 P1 O2 Cu3 -4.3(3) . . . 1_565 ?
C1 P1 O2 Cu3 109.5(3) . . . 1_565 ?
O1 P1 O3 Cu2 -67.2(3) . . . . ?
O2 P1 O3 Cu2 165.8(2) . . . . ?
C1 P1 O3 Cu2 49.9(3) . . . . ?
O5 C7 O4 Cu2 162.9(3) . . . . ?
C6 C7 O4 Cu2 -17.0(7) . . . . ?
O8 P2 O6 Cu2 127.1(3) . . . . ?
O7 P2 O6 Cu2 0.0(4) . . . . ?
C8 P2 O6 Cu2 -113.9(3) . . . . ?
O8 P2 O7 Cu3 80.0(3) . . . . ?
O6 P2 O7 Cu3 -152.8(3) . . . . ?
C8 P2 O7 Cu3 -38.6(4) . . . . ?
O6 P2 O8 Cu1 -27.4(3) . . . 2_646 ?
O7 P2 O8 Cu1 97.4(3) . . . 2_646 ?
C8 P2 O8 Cu1 -145.5(3) . . . 2_646 ?
O10 C14 O9 Cu3 -169.7(3) . . . . ?
C13 C14 O9 Cu3 11.7(7) . . . . ?
O9 C14 O10 Cu1 6.0(5) . . . 1_645 ?
C13 C14 O10 Cu1 -175.4(3) . . . 1_645 ?

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
O5W H5WB O6 0.85 2.58 3.260(5) 137.9 1_545
O5W H5WB O3 0.85 1.91 2.697(5) 153.1 1_545
O5W H5WA O5 0.85 1.89 2.669(5) 152.4 1_645
O4W H4WB O1W 0.85 1.98 2.778(5) 157.0 2_636
O4W H4WA O4 0.85 2.22 2.934(5) 141.1 2_646
O3W H3WB O1W 0.85 2.43 3.176(5) 146.5 1_545
O3W H3WB O7 0.85 2.14 2.711(5) 123.8 .
O3W H3WB O2 0.85 2.46 3.065(5) 129.2 1_545
O3W H3WA O10 0.85 2.15 2.780(4) 131.2 1_455
O2W H2WB O8 0.85 2.32 2.935(5) 129.7 1_465
O2W H2WA O5 0.85 1.89 2.633(5) 144.7 2_556
O1W H1WB O6 0.85 2.43 3.029(5) 128.0 2_656
O1W H1WB O3 0.85 2.05 2.818(5) 150.2 2_656
O1W H1WA O4W 0.85 2.61 3.346(5) 145.1 1_565
O1W H1WA O7 0.85 2.54 3.132(4) 127.8 1_565
O1W H1WA O2 0.85 2.25 2.888(5) 132.4 .

_refine_diff_density_max         0.496
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.086

_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 1823684'
_audit_update_record             
;
2018-04-05 deposited with the CCDC.
2018-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H12 Cu3 O12 P2'
_chemical_formula_sum            'C14 H12 Cu3 O12 P2'
_chemical_formula_weight         624.80

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

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

_cell_length_a                   22.650(3)
_cell_length_b                   8.8845(11)
_cell_length_c                   8.9245(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1795.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    2610
_cell_measurement_theta_min      2.463
_cell_measurement_theta_max      23.892

_exptl_crystal_description       sheet-like
_exptl_crystal_colour            'light blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.311
_exptl_crystal_F_000             1236
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    3.768
_shelx_estimated_absorpt_T_min   0.519
_shelx_estimated_absorpt_T_max   0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.500
_exptl_absorpt_correction_T_max  0.831
_exptl_absorpt_process_details   'SADABS(Bruker, 2000)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9533
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0739
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.462
_diffrn_reflns_theta_max         23.733
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.838
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.838
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.838
_reflns_number_total             1364
_reflns_number_gt                1094
_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       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0365P)²+4.9220P] 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         1364
_refine_ls_number_parameters     141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0721
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.38216(10) 0.7500 0.0102(2) Uani 1 2 d S T P . .
Cu2 Cu 0.43471(3) 0.13637(6) 0.18085(6) 0.01066(19) Uani 1 1 d . . . . .
P1 P 0.43386(6) 0.18493(14) 0.52664(14) 0.0111(3) Uani 1 1 d . . . . .
C1 C 0.3608(2) 0.2599(5) 0.4862(5) 0.0120(11) Uani 1 1 d . . . . .
C2 C 0.3112(2) 0.2102(6) 0.5631(5) 0.0156(12) Uani 1 1 d . . . . .
H2 H 0.3151 0.1330 0.6361 0.019 Uiso 1 1 calc R U . . .
C3 C 0.2559(2) 0.2716(6) 0.5351(6) 0.0179(13) Uani 1 1 d . . . . .
H3 H 0.2223 0.2341 0.5867 0.021 Uiso 1 1 calc R U . . .
C4 C 0.2496(2) 0.3862(6) 0.4331(5) 0.0170(12) Uani 1 1 d . . . . .
H4 H 0.2116 0.4271 0.4136 0.020 Uiso 1 1 calc R U . . .
C5 C 0.2989(2) 0.4426(6) 0.3583(5) 0.0154(12) Uani 1 1 d . . . . .
H5 H 0.2950 0.5243 0.2904 0.018 Uiso 1 1 calc R U . . .
C6 C 0.3539(2) 0.3781(5) 0.3840(5) 0.0107(11) Uani 1 1 d . . . . .
C7 C 0.4065(2) 0.4371(6) 0.3003(5) 0.0105(11) Uani 1 1 d . . . . .
O1 O 0.47425(14) 0.3178(4) 0.5558(3) 0.0127(8) Uani 1 1 d . . . . .
O2 O 0.42609(15) 0.0788(4) 0.6589(3) 0.0136(8) Uani 1 1 d . . . . .
O3 O 0.45522(15) 0.0986(4) 0.3863(3) 0.0141(8) Uani 1 1 d . . . . .
O4 O 0.43579(15) 0.3552(4) 0.2135(3) 0.0124(8) Uani 1 1 d . . . . .
O5 O 0.42027(14) 0.5748(4) 0.3232(3) 0.0120(8) Uani 1 1 d . . . . .
O1W O 0.40174(14) 0.1703(4) -0.0181(3) 0.0122(8) Uani 1 1 d . . . . .
H1WA H 0.4167 0.1109 -0.0824 0.018 Uiso 1 1 d R U . . .
H1WB H 0.4060 0.2612 -0.0457 0.018 Uiso 1 1 d 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 O1 1.916(3) 3_656 ?
Cu1 O1 1.916(3) . ?
Cu1 O5 1.958(3) 5_666 ?
Cu1 O5 1.958(3) 7_566 ?
Cu2 O3 1.921(3) . ?
Cu2 O2 1.932(3) 7 ?
Cu2 O1W 1.949(3) . ?
Cu2 O4 1.966(3) . ?
P1 O1 1.516(3) . ?
P1 O2 1.521(3) . ?
P1 O3 1.546(3) . ?
P1 C1 1.821(5) . ?
C1 C2 1.389(7) . ?
C1 C6 1.399(7) . ?
C2 C3 1.387(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.500(7) . ?
C7 O4 1.253(6) . ?
C7 O5 1.280(6) . ?
O2 Cu2 1.932(3) 7_556 ?
O5 Cu1 1.958(3) 5_666 ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8501 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 145.3(2) 3_656 . ?
O1 Cu1 O5 94.55(13) 3_656 5_666 ?
O1 Cu1 O5 92.13(13) . 5_666 ?
O1 Cu1 O5 92.13(13) 3_656 7_566 ?
O1 Cu1 O5 94.55(13) . 7_566 ?
O5 Cu1 O5 157.5(2) 5_666 7_566 ?
O3 Cu2 O2 87.04(14) . 7 ?
O3 Cu2 O1W 171.44(14) . . ?
O2 Cu2 O1W 91.26(13) 7 . ?
O3 Cu2 O4 91.63(13) . . ?
O2 Cu2 O4 174.27(14) 7 . ?
O1W Cu2 O4 89.23(13) . . ?
O1 P1 O2 114.81(19) . . ?
O1 P1 O3 109.66(19) . . ?
O2 P1 O3 110.93(19) . . ?
O1 P1 C1 107.3(2) . . ?
O2 P1 C1 106.0(2) . . ?
O3 P1 C1 107.8(2) . . ?
C2 C1 C6 118.1(4) . . ?
C2 C1 P1 121.4(4) . . ?
C6 C1 P1 120.3(4) . . ?
C3 C2 C1 121.0(5) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C4 C3 C2 120.4(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.0(5) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.4(5) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 121.1(5) . . ?
C5 C6 C7 119.0(4) . . ?
C1 C6 C7 120.0(4) . . ?
O4 C7 O5 121.6(5) . . ?
O4 C7 C6 121.7(4) . . ?
O5 C7 C6 116.6(4) . . ?
P1 O1 Cu1 124.84(19) . . ?
P1 O2 Cu2 132.9(2) . 7_556 ?
P1 O3 Cu2 127.6(2) . . ?
C7 O4 Cu2 131.2(3) . . ?
C7 O5 Cu1 111.0(3) . 5_666 ?
Cu2 O1W H1WA 111.5 . . ?
Cu2 O1W H1WB 111.6 . . ?
H1WA O1W H1WB 110.4 . . ?

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
O1 P1 C1 C2 -127.5(4) . . . . ?
O2 P1 C1 C2 -4.4(4) . . . . ?
O3 P1 C1 C2 114.5(4) . . . . ?
O1 P1 C1 C6 47.6(4) . . . . ?
O2 P1 C1 C6 170.7(4) . . . . ?
O3 P1 C1 C6 -70.5(4) . . . . ?
C6 C1 C2 C3 2.6(7) . . . . ?
P1 C1 C2 C3 177.8(4) . . . . ?
C1 C2 C3 C4 -1.9(8) . . . . ?
C2 C3 C4 C5 -0.7(8) . . . . ?
C3 C4 C5 C6 2.3(7) . . . . ?
C4 C5 C6 C1 -1.5(7) . . . . ?
C4 C5 C6 C7 178.6(4) . . . . ?
C2 C1 C6 C5 -1.0(7) . . . . ?
P1 C1 C6 C5 -176.2(4) . . . . ?
C2 C1 C6 C7 179.0(4) . . . . ?
P1 C1 C6 C7 3.8(6) . . . . ?
C5 C6 C7 O4 -118.7(5) . . . . ?
C1 C6 C7 O4 61.3(6) . . . . ?
C5 C6 C7 O5 62.1(6) . . . . ?
C1 C6 C7 O5 -117.9(5) . . . . ?
O2 P1 O1 Cu1 -14.5(3) . . . . ?
O3 P1 O1 Cu1 -140.1(2) . . . . ?
C1 P1 O1 Cu1 103.0(3) . . . . ?
O1 P1 O2 Cu2 -127.7(3) . . . 7_556 ?
O3 P1 O2 Cu2 -2.7(4) . . . 7_556 ?
C1 P1 O2 Cu2 114.0(3) . . . 7_556 ?
O1 P1 O3 Cu2 -87.5(3) . . . . ?
O2 P1 O3 Cu2 144.6(2) . . . . ?
C1 P1 O3 Cu2 29.0(3) . . . . ?
O5 C7 O4 Cu2 168.2(3) . . . . ?
C6 C7 O4 Cu2 -11.0(7) . . . . ?
O4 C7 O5 Cu1 -14.4(5) . . . 5_666 ?
C6 C7 O5 Cu1 164.9(3) . . . 5_666 ?

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 H1WB O5 0.85 1.90 2.703(4) 158.2 7_565
O1W H1WA O3 0.85 2.07 2.811(5) 144.6 7
O1W H1WA O2 0.85 2.34 3.046(4) 141.2 1_554

_refine_diff_density_max         0.573
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.109

_shelxl_version_number           2013-4



