# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_CHD123
_database_code_depnum_ccdc_archive 'CCDC 1465329'
_audit_update_record             
;
2016-03-13 deposited with the CCDC.
2016-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
"4-diethylphosphono-4'-biphenyl carboxylic acid methyl ester"
_chemical_name_common            ?
_chemical_melting_point          350
_chemical_formula_moiety         'C18 H21 O5 P'
_chemical_formula_sum            'C18 H21 O5 P'
_chemical_formula_weight         348.32

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'

_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                   8.094(2)
_cell_length_b                   8.186(2)
_cell_length_c                   13.626(4)
_cell_angle_alpha                104.044(15)
_cell_angle_beta                 92.510(15)
_cell_angle_gamma                99.071(14)
_cell_volume                     861.7(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2538
_cell_measurement_theta_min      2.785
_cell_measurement_theta_max      27.988

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             368
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.184
_shelx_estimated_absorpt_T_min   0.852
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6201
_exptl_absorpt_correction_T_max  0.7444
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11291
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.546
_diffrn_reflns_theta_max         25.847
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3248
_reflns_number_gt                2650
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND 3.2 (Crystal Impact, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_refine_special_details          
;
Bruker AXS. (2012). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker AXS. (2012). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker AXS. (2012). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Crystal Impact (2009). DIAMOND. Version3.2.
Crystal Impact GbR, Bonn, Germany.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0925P)²+0.6193P] 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         3248
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1750
_refine_ls_wR_factor_gt          0.1632
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
P1 P 0.24852(8) 0.92073(9) 0.12500(5) 0.0342(2) Uani 1 1 d . . . . .
O1 O 0.2802(3) 1.1200(3) 0.14994(18) 0.0530(6) Uani 1 1 d . . . . .
O4 O 1.3085(2) 0.6650(3) 0.56645(15) 0.0417(5) Uani 1 1 d . . . . .
C1 C 0.4148(3) 0.8832(3) 0.20299(19) 0.0305(5) Uani 1 1 d . . . . .
C2 C 0.3775(3) 0.8424(3) 0.2935(2) 0.0350(6) Uani 1 1 d . . . . .
H2 H 0.2672 0.8326 0.3110 0.042 Uiso 1 1 calc R U . . .
O2 O 0.0821(2) 0.8391(3) 0.14229(18) 0.0572(6) Uani 1 1 d . . . . .
C3 C 0.5007(3) 0.8162(3) 0.3581(2) 0.0355(6) Uani 1 1 d . . . . .
H3 H 0.4730 0.7919 0.4192 0.043 Uiso 1 1 calc R U . . .
O3 O 0.2919(3) 0.8701(3) 0.01184(16) 0.0501(6) Uani 1 1 d . . . . .
C4 C 0.6676(3) 0.8257(3) 0.33283(19) 0.0282(5) Uani 1 1 d . . . . .
C16 C 0.1967(4) 1.3910(4) 0.1796(3) 0.0608(9) Uani 1 1 d . . . . .
H16A H 0.3105 1.4403 0.1741 0.091 Uiso 1 1 calc R U . . .
H16B H 0.1813 1.3916 0.2491 0.091 Uiso 1 1 calc R U . . .
H16C H 0.1218 1.4566 0.1566 0.091 Uiso 1 1 calc R U . . .
C15 C 0.1601(4) 1.2121(4) 0.1159(3) 0.0605(9) Uani 1 1 d . . . . .
H15A H 0.0467 1.1594 0.1230 0.073 Uiso 1 1 calc R U . . .
H15B H 0.1700 1.2104 0.0450 0.073 Uiso 1 1 calc R U . . .
C18 C 0.3619(8) 0.6049(8) -0.0679(6) 0.144(3) Uani 1 1 d . . . . .
H18A H 0.4603 0.6710 -0.0848 0.217 Uiso 1 1 calc R U . . .
H18B H 0.3240 0.5057 -0.1229 0.217 Uiso 1 1 calc R U . . .
H18C H 0.3881 0.5699 -0.0076 0.217 Uiso 1 1 calc R U . . .
C5 C 0.7048(3) 0.8654(3) 0.2413(2) 0.0321(6) Uani 1 1 d . . . . .
H5 H 0.8145 0.8725 0.2229 0.039 Uiso 1 1 calc R U . . .
O5 O 1.1551(3) 0.7270(3) 0.69863(15) 0.0464(5) Uani 1 1 d . . . . .
C6 C 0.5810(3) 0.8941(3) 0.1774(2) 0.0332(6) Uani 1 1 d . . . . .
H6 H 0.6085 0.9209 0.1169 0.040 Uiso 1 1 calc R U . . .
C7 C 0.7988(3) 0.7957(3) 0.40235(19) 0.0285(5) Uani 1 1 d . . . . .
C8 C 0.7935(3) 0.8474(3) 0.5075(2) 0.0350(6) Uani 1 1 d . . . . .
H8 H 0.7067 0.9022 0.5336 0.042 Uiso 1 1 calc R U . . .
C9 C 0.9134(3) 0.8193(3) 0.5738(2) 0.0361(6) Uani 1 1 d . . . . .
H9 H 0.9070 0.8551 0.6435 0.043 Uiso 1 1 calc R U . . .
C10 C 1.0442(3) 0.7372(3) 0.53572(19) 0.0299(5) Uani 1 1 d . . . . .
C13 C 1.1715(3) 0.7099(3) 0.6101(2) 0.0330(6) Uani 1 1 d . . . . .
C11 C 1.0510(3) 0.6842(3) 0.4314(2) 0.0309(6) Uani 1 1 d . . . . .
H11 H 1.1373 0.6285 0.4055 0.037 Uiso 1 1 calc R U . . .
C14 C 1.4393(3) 0.6398(4) 0.6345(2) 0.0471(7) Uani 1 1 d . . . . .
H14A H 1.5317 0.6079 0.5968 0.071 Uiso 1 1 calc R U . . .
H14B H 1.3958 0.5508 0.6659 0.071 Uiso 1 1 calc R U . . .
H14C H 1.4771 0.7441 0.6859 0.071 Uiso 1 1 calc R U . . .
C12 C 0.9300(3) 0.7135(3) 0.3653(2) 0.0310(6) Uani 1 1 d . . . . .
H12 H 0.9367 0.6779 0.2956 0.037 Uiso 1 1 calc R U . . .
C17 C 0.2407(6) 0.6999(7) -0.0518(4) 0.106(2) Uani 1 1 d . . . . .
H17A H 0.1515 0.6409 -0.0213 0.127 Uiso 1 1 calc R U . . .
H17B H 0.1943 0.7079 -0.1170 0.127 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
P1 O2 1.462(2) . ?
P1 O1 1.560(2) . ?
P1 O3 1.567(2) . ?
P1 C1 1.788(3) . ?
O1 C15 1.446(4) . ?
O4 C13 1.341(3) . ?
O4 C14 1.449(3) . ?
C1 C2 1.387(4) . ?
C1 C6 1.400(3) . ?
C2 C3 1.378(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(3) . ?
C3 H3 0.9300 . ?
O3 C17 1.437(5) . ?
C4 C5 1.397(4) . ?
C4 C7 1.481(4) . ?
C16 C15 1.486(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 C17 1.338(7) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9300 . ?
O5 C13 1.195(3) . ?
C6 H6 0.9300 . ?
C7 C12 1.394(3) . ?
C7 C8 1.397(4) . ?
C8 C9 1.380(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.395(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.388(4) . ?
C10 C13 1.494(4) . ?
C11 C12 1.389(4) . ?
C11 H11 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C12 H12 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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 P1 O1 116.11(13) . . ?
O2 P1 O3 113.98(13) . . ?
O1 P1 O3 102.44(13) . . ?
O2 P1 C1 113.48(13) . . ?
O1 P1 C1 101.48(11) . . ?
O3 P1 C1 108.04(11) . . ?
C15 O1 P1 121.6(2) . . ?
C13 O4 C14 115.3(2) . . ?
C2 C1 C6 118.4(2) . . ?
C2 C1 P1 118.48(18) . . ?
C6 C1 P1 123.1(2) . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 120.8(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C17 O3 P1 122.1(3) . . ?
C5 C4 C3 117.9(2) . . ?
C5 C4 C7 121.7(2) . . ?
C3 C4 C7 120.4(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C15 C16 107.6(3) . . ?
O1 C15 H15A 110.2 . . ?
C16 C15 H15A 110.2 . . ?
O1 C15 H15B 110.2 . . ?
C16 C15 H15B 110.2 . . ?
H15A C15 H15B 108.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 C5 C4 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 120.6(2) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C12 C7 C8 117.9(2) . . ?
C12 C7 C4 121.3(2) . . ?
C8 C7 C4 120.8(2) . . ?
C9 C8 C7 121.9(2) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 119.7(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 119.2(2) . . ?
C11 C10 C13 122.8(2) . . ?
C9 C10 C13 117.9(2) . . ?
O5 C13 O4 123.5(2) . . ?
O5 C13 C10 124.4(2) . . ?
O4 C13 C10 112.2(2) . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C12 C7 120.7(2) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
C18 C17 O3 115.5(5) . . ?
C18 C17 H17A 108.4 . . ?
O3 C17 H17A 108.4 . . ?
C18 C17 H17B 108.4 . . ?
O3 C17 H17B 108.4 . . ?
H17A C17 H17B 107.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 P1 O1 C15 -46.8(3) . . . . ?
O3 P1 O1 C15 78.1(3) . . . . ?
C1 P1 O1 C15 -170.3(3) . . . . ?
O2 P1 C1 C2 -23.6(3) . . . . ?
O1 P1 C1 C2 101.7(2) . . . . ?
O3 P1 C1 C2 -151.0(2) . . . . ?
O2 P1 C1 C6 156.8(2) . . . . ?
O1 P1 C1 C6 -77.9(2) . . . . ?
O3 P1 C1 C6 29.4(2) . . . . ?
C6 C1 C2 C3 1.2(4) . . . . ?
P1 C1 C2 C3 -178.4(2) . . . . ?
C1 C2 C3 C4 -1.6(4) . . . . ?
O2 P1 O3 C17 -37.5(3) . . . . ?
O1 P1 O3 C17 -163.7(3) . . . . ?
C1 P1 O3 C17 89.7(3) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C2 C3 C4 C7 -179.4(2) . . . . ?
P1 O1 C15 C16 160.8(2) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C7 C4 C5 C6 -179.6(2) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C2 C1 C6 C5 -0.2(4) . . . . ?
P1 C1 C6 C5 179.36(19) . . . . ?
C5 C4 C7 C12 -36.2(3) . . . . ?
C3 C4 C7 C12 144.3(2) . . . . ?
C5 C4 C7 C8 144.6(2) . . . . ?
C3 C4 C7 C8 -34.9(3) . . . . ?
C12 C7 C8 C9 0.1(4) . . . . ?
C4 C7 C8 C9 179.4(2) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C8 C9 C10 C13 179.8(2) . . . . ?
C14 O4 C13 O5 -0.7(4) . . . . ?
C14 O4 C13 C10 178.8(2) . . . . ?
C11 C10 C13 O5 -166.8(2) . . . . ?
C9 C10 C13 O5 13.1(4) . . . . ?
C11 C10 C13 O4 13.8(3) . . . . ?
C9 C10 C13 O4 -166.3(2) . . . . ?
C9 C10 C11 C12 0.5(4) . . . . ?
C13 C10 C11 C12 -179.6(2) . . . . ?
C10 C11 C12 C7 -0.4(4) . . . . ?
C8 C7 C12 C11 0.1(3) . . . . ?
C4 C7 C12 C11 -179.1(2) . . . . ?
P1 O3 C17 C18 -104.0(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
C17 H17A O2 0.97 2.56 3.039(5) 110.5 .
C17 H17B O5 0.97 2.56 3.507(7) 164.2 1_454

_refine_diff_density_max         0.526
_refine_diff_density_min         -0.472
_refine_diff_density_rms         0.068


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method mesitylene
####################################################################### 
# 
# 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_BPPA_Zn
_database_code_depnum_ccdc_archive 'CCDC 1465330'
_audit_update_record             
;
2016-03-13 deposited with the CCDC.
2016-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 O5 P Zn'
_chemical_formula_sum            'C13 H9 O5 P Zn'
_chemical_formula_weight         341.54

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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   5.2848(12)
_cell_length_b                   8.1031(18)
_cell_length_c                   27.371(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.766(12)
_cell_angle_gamma                90
_cell_volume                     1171.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2538
_cell_measurement_theta_min      2.284
_cell_measurement_theta_max      27.484

_exptl_crystal_description       spheric
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.936
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.025
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.025
_exptl_absorpt_coefficient_mu    2.249
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7237
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5207
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.233
_diffrn_reflns_theta_max         24.965
_diffrn_reflns_theta_full        24.965
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             1106
_reflns_number_gt                912
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND 3.2 (Crystal Impact, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_refine_special_details          
;
Bruker AXS. (2012). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker AXS. (2012). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker AXS. (2012). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Crystal Impact (2009). DIAMOND. Version3.2.
Crystal Impact GbR, Bonn, Germany.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0504P)²+40.4792P] 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         1106
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0681
_refine_ls_wR_factor_ref         0.1630
_refine_ls_wR_factor_gt          0.1520
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
Zn Zn 0.5000 0.81938(15) 0.5000 0.0173(4) Uani 1 2 d S T P . .
P P 0.5626(4) 0.5000 0.43826(9) 0.0083(6) Uani 1 2 d S T P A .
O1 O 0.4161(8) 0.6556(5) 0.45089(16) 0.0089(10) Uani 1 1 d . . . . .
O2 O 0.8314(16) 0.5000 0.4632(3) 0.0332(15) Uani 1 2 d S T P . .
C1 C 0.6120(18) 0.5000 0.3737(4) 0.013(2) Uani 1 2 d S T P . .
C2 C 0.813(3) 0.418(2) 0.3553(5) 0.025(3) Uani 0.5 1 d . . P A -1
H2 H 0.9253 0.3599 0.3770 0.029 Uiso 0.5 1 calc R U P A -1
C3 C 0.856(3) 0.416(2) 0.3060(5) 0.027(4) Uani 0.5 1 d . . P A -1
H3 H 0.9967 0.3567 0.2944 0.032 Uiso 0.5 1 calc R U P A -1
C4 C 0.6990(19) 0.5000 0.2727(4) 0.017(2) Uani 1 2 d S T P . .
C5 C 0.493(3) 0.581(2) 0.2915(5) 0.023(3) Uani 0.5 1 d . . P A -2
H5 H 0.3779 0.6370 0.2697 0.028 Uiso 0.5 1 calc R U P A -2
C6 C 0.449(3) 0.584(2) 0.3414(5) 0.025(3) Uani 0.5 1 d . . P A -2
H6 H 0.3089 0.6429 0.3534 0.029 Uiso 0.5 1 calc R U P A -2
C7 C 0.750(2) 0.5000 0.2192(4) 0.021(2) Uani 1 2 d S T P A .
C8 C 0.958(3) 0.418(3) 0.2015(6) 0.038(5) Uani 0.5 1 d . . P A -3
H8 H 1.0693 0.3628 0.2239 0.046 Uiso 0.5 1 calc R U P A -3
C9 C 1.009(4) 0.415(3) 0.1526(7) 0.048(5) Uani 0.5 1 d . . P A -3
H9 H 1.1509 0.3560 0.1415 0.057 Uiso 0.5 1 calc R U P A -3
C10 C 0.848(3) 0.5000 0.1191(4) 0.037(3) Uani 1 2 d S T P . .
C11 C 0.641(4) 0.577(3) 0.1365(6) 0.048(6) Uani 0.5 1 d . . P A -4
H11 H 0.5263 0.6303 0.1143 0.057 Uiso 0.5 1 calc R U P A -4
C12 C 0.596(3) 0.579(3) 0.1853(6) 0.037(5) Uani 0.5 1 d . . P A -4
H12 H 0.4517 0.6368 0.1963 0.045 Uiso 0.5 1 calc R U P A -4
C13 C 0.910(3) 0.5000 0.0661(5) 0.055(4) Uani 1 2 d S T P A .
O3 O 0.766(2) 0.5737(15) 0.0382(4) 0.0332(15) Uani 0.5 1 d . . P A -5
H3A H 0.8175 0.5662 0.0096 0.050 Uiso 0.5 1 calc R U P A -5
O4 O 1.103(2) 0.4214(16) 0.0530(4) 0.0332(15) Uani 0.5 1 d . . P A -5


_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
Zn O1 1.931(4) . ?
Zn O1 1.931(4) 2_656 ?
Zn O2 1.973(6) 7_666 ?
Zn O2 1.973(5) 3_455 ?
Zn Zn 2.8717(11) 7_566 ?
Zn Zn 2.8717(11) 7_666 ?
Zn Zn 2.927(3) 5_676 ?
P O1 1.525(5) 6_565 ?
P O1 1.525(4) . ?
P O2 1.557(9) . ?
P C1 1.793(10) . ?
O2 Zn 1.973(5) 7_666 ?
O2 Zn 1.973(5) 3_545 ?
C1 C2 1.363(17) . ?
C1 C6 1.391(17) . ?
C2 C3 1.38(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(18) . ?
C4 C7 1.497(14) . ?
C5 C6 1.39(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.37(2) . ?
C7 C8 1.38(2) . ?
C8 C9 1.37(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.41(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.36(2) . ?
C10 C13 1.495(18) . ?
C11 C12 1.37(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 O3 1.221(16) . ?
C13 O4 1.262(16) . ?
O3 H3A 0.8400 . ?

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 Zn O1 93.2(3) . 2_656 ?
O1 Zn O2 162.8(3) . 7_666 ?
O1 Zn O2 93.7(2) 2_656 7_666 ?
O1 Zn O2 93.7(2) . 3_455 ?
O1 Zn O2 162.8(3) 2_656 3_455 ?
O2 Zn O2 84.2(4) 7_666 3_455 ?
O1 Zn Zn 62.57(13) . 7_566 ?
O1 Zn Zn 85.55(13) 2_656 7_566 ?
O2 Zn Zn 133.8(2) 7_666 7_566 ?
O2 Zn Zn 83.6(2) 3_455 7_566 ?
O1 Zn Zn 85.55(13) . 7_666 ?
O1 Zn Zn 62.57(13) 2_656 7_666 ?
O2 Zn Zn 83.6(2) 7_666 7_666 ?
O2 Zn Zn 133.8(2) 3_455 7_666 ?
Zn Zn Zn 133.90(9) 7_566 7_666 ?
O1 Zn Zn 133.42(13) . 5_676 ?
O1 Zn Zn 133.42(13) 2_656 5_676 ?
O2 Zn Zn 42.12(18) 7_666 5_676 ?
O2 Zn Zn 42.12(18) 3_455 5_676 ?
Zn Zn Zn 113.05(4) 7_566 5_676 ?
Zn Zn Zn 113.05(5) 7_666 5_676 ?
O1 P O1 111.6(4) 6_565 . ?
O1 P O2 111.3(2) 6_565 . ?
O1 P O2 111.3(2) . . ?
O1 P C1 108.3(2) 6_565 . ?
O1 P C1 108.3(2) . . ?
O2 P C1 105.9(4) . . ?
P O1 Zn 128.2(3) . . ?
P O2 Zn 128.0(3) . 7_666 ?
P O2 Zn 128.0(3) . 3_545 ?
Zn O2 Zn 95.8(4) 7_666 3_545 ?
C2 C1 P 120.2(8) . . ?
C6 C1 P 121.3(8) . . ?
C1 C2 C3 121.4(13) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C4 121.8(14) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C7 122.1(9) . . ?
C3 C4 C7 121.2(9) . . ?
C4 C5 C6 121.7(13) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 120.0(13) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C12 C7 C4 122.5(10) . . ?
C8 C7 C4 120.8(10) . . ?
C9 C8 C7 122.1(16) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C10 119.7(17) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C13 122.8(12) . . ?
C9 C10 C13 119.2(12) . . ?
C10 C11 C12 121.1(16) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C7 122.4(16) . . ?
C11 C12 H12 118.8 . . ?
C7 C12 H12 118.8 . . ?
O3 C13 O4 124.2(14) . . ?
O3 C13 C10 117.2(12) . . ?
O4 C13 C10 118.6(11) . . ?
C13 O3 H3A 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 P O1 Zn 113.4(3) 6_565 . . . ?
O2 P O1 Zn -11.5(5) . . . . ?
C1 P O1 Zn -127.5(4) . . . . ?
O1 P O2 Zn -132.8(4) 6_565 . . 7_666 ?
O1 P O2 Zn -7.7(6) . . . 7_666 ?
C1 P O2 Zn 109.8(5) . . . 7_666 ?
O1 P O2 Zn 7.7(6) 6_565 . . 3_545 ?
O1 P O2 Zn 132.8(4) . . . 3_545 ?
C1 P O2 Zn -109.8(5) . . . 3_545 ?
O1 P C1 C2 -84.9(10) 6_565 . . . ?
O1 P C1 C2 154.0(9) . . . . ?
O2 P C1 C2 34.5(9) . . . . ?
O1 P C1 C6 95.5(9) 6_565 . . . ?
O1 P C1 C6 -25.6(10) . . . . ?
O2 P C1 C6 -145.1(9) . . . . ?
P C1 C2 C3 -179.6(12) . . . . ?
C1 C2 C3 C4 1(2) . . . . ?
C2 C3 C4 C7 179.0(13) . . . . ?
C7 C4 C5 C6 -178.5(12) . . . . ?
P C1 C6 C5 -179.9(12) . . . . ?
C4 C5 C6 C1 -2(2) . . . . ?
C4 C7 C8 C9 179.4(16) . . . . ?
C7 C8 C9 C10 1(3) . . . . ?
C8 C9 C10 C13 178.1(16) . . . . ?
C13 C10 C11 C12 -177.8(15) . . . . ?
C10 C11 C12 C7 -2(3) . . . . ?
C4 C7 C12 C11 -179.2(15) . . . . ?

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
C2 H2 O1 0.95 2.62 3.400(16) 140.2 3_545

_refine_diff_density_max         3.634
_refine_diff_density_min         -1.723
_refine_diff_density_rms         0.184


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method water
####################################################################### 
# 
# 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_BPPA_Hg
_database_code_depnum_ccdc_archive 'CCDC 1465331'
_audit_update_record             
;
2016-05-12 deposited with the CCDC.
2016-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 Hg O5 P'
_chemical_formula_sum            'C13 H10 Hg O5 P'
_chemical_formula_weight         477.77

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'
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'
Hg Hg -2.3894 9.2266 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 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+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   59.003(11)
_cell_length_b                   5.4907(9)
_cell_length_c                   7.8375(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.644(9)
_cell_angle_gamma                90
_cell_volume                     2534.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4884
_cell_measurement_theta_min      2.767
_cell_measurement_theta_max      29.785

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.505
_exptl_crystal_F_000             1784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.010
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    12.290
_shelx_estimated_absorpt_T_min   0.887
_shelx_estimated_absorpt_T_max   0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5153
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11056
_diffrn_reflns_av_unetI/netI     0.0861
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_limit_h_min       -70
_diffrn_reflns_limit_h_max       65
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.075
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_full        24.990
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.947
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.947
_reflns_number_total             2121
_reflns_number_gt                1633
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND 3.2 (Crystal Impact, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_refine_special_details          
;
Bruker AXS. (2012). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker AXS. (2012). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker AXS. (2012). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Crystal Impact (2009). DIAMOND. Version3.2.
Crystal Impact GbR, Bonn, Germany.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0836P)²+333.1455P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00056(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2121
_refine_ls_number_parameters     155
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0699
_refine_ls_wR_factor_ref         0.1763
_refine_ls_wR_factor_gt          0.1646
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
Hg1 Hg 0.48193(2) 0.15142(13) 0.32640(8) 0.0122(4) Uani 1 1 d . . . . .
O1 O 0.4538(2) 0.189(3) 0.4792(17) 0.026(2) Uani 1 1 d . . . . .
C1 C 0.4198(3) 0.317(4) 0.669(2) 0.016(3) Uani 1 1 d . . . . .
P1 P 0.44942(8) 0.3415(9) 0.6344(6) 0.0115(11) Uani 1 1 d . . . . .
O3 O 0.4530(2) 0.618(2) 0.5941(15) 0.015(3) Uani 1 1 d D . . . .
H3 H 0.456(3) 0.62(4) 0.484(9) 0.022 Uiso 1 1 d D U . . .
O4 O 0.2666(3) 0.401(5) 0.856(3) 0.076(8) Uani 1 1 d . . . . .
H4 H 0.2538 0.3933 0.8963 0.114 Uiso 1 1 calc R U . . .
C5 C 0.3816(3) 0.465(5) 0.647(2) 0.024(4) Uani 1 1 d . . . . .
H5 H 0.3715 0.5900 0.6076 0.028 Uiso 1 1 calc R U . . .
C2 C 0.4118(3) 0.106(4) 0.755(2) 0.016(3) Uani 1 1 d . . . . .
H2 H 0.4223 -0.0175 0.7903 0.020 Uiso 1 1 calc R U . . .
O2 O 0.4636(2) 0.272(3) 0.7983(17) 0.026(2) Uani 1 1 d . . . . .
C8 C 0.3406(3) 0.063(5) 0.870(3) 0.034(6) Uani 1 1 d . . . . .
H8 H 0.3505 -0.0673 0.9022 0.041 Uiso 1 1 calc R U . . .
O5 O 0.2738(2) 0.088(3) 1.0232(18) 0.026(2) Uani 1 1 d . . . . .
C3 C 0.3893(3) 0.078(5) 0.787(3) 0.030(6) Uani 1 1 d . . . . .
H3A H 0.3843 -0.0629 0.8438 0.036 Uiso 1 1 calc R U . . .
C4 C 0.3732(3) 0.265(5) 0.733(2) 0.024(4) Uani 1 1 d . . . . .
C6 C 0.4045(3) 0.486(4) 0.616(3) 0.028(6) Uani 1 1 d . . . . .
H6 H 0.4095 0.6241 0.5563 0.033 Uiso 1 1 calc R U . . .
C7 C 0.3489(3) 0.258(5) 0.778(2) 0.029(4) Uani 1 1 d . . . . .
C9 C 0.3181(4) 0.056(6) 0.915(3) 0.044(7) Uani 1 1 d . . . . .
H9 H 0.3130 -0.0753 0.9810 0.053 Uiso 1 1 calc R U . . .
C10 C 0.3035(3) 0.238(6) 0.863(3) 0.034(6) Uani 1 1 d . . . . .
C12 C 0.3337(3) 0.426(5) 0.722(2) 0.029(4) Uani 1 1 d . . . . .
H12 H 0.3385 0.5508 0.6483 0.035 Uiso 1 1 calc R U . . .
C13 C 0.2794(3) 0.237(6) 0.923(3) 0.039(7) Uani 1 1 d . . . . .
C11 C 0.3109(3) 0.427(6) 0.765(3) 0.036(6) Uani 1 1 d . . . . .
H11 H 0.3009 0.5547 0.7281 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
Hg1 O1 2.118(13) . ?
Hg1 Hg1 2.5116(14) 2_655 ?
Hg1 O2 2.566(16) 6 ?
O1 P1 1.512(15) . ?
C1 C6 1.34(3) . ?
C1 C2 1.43(3) . ?
C1 P1 1.791(19) . ?
P1 O2 1.537(14) . ?
P1 O3 1.566(14) . ?
O3 H3 0.89(5) . ?
O4 C13 1.27(3) . ?
O4 H4 0.8400 . ?
C5 C6 1.39(3) . ?
C5 C4 1.40(3) . ?
C5 H5 0.9500 . ?
C2 C3 1.37(3) . ?
C2 H2 0.9500 . ?
O2 Hg1 2.566(16) 6_556 ?
C8 C7 1.40(3) . ?
C8 C9 1.40(3) . ?
C8 H8 0.9500 . ?
O5 C13 1.20(3) . ?
C3 C4 1.44(3) . ?
C3 H3A 0.9500 . ?
C4 C7 1.50(3) . ?
C6 H6 0.9500 . ?
C7 C12 1.34(3) . ?
C9 C10 1.36(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.38(4) . ?
C10 C13 1.52(3) . ?
C12 C11 1.41(3) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?

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 Hg1 Hg1 171.7(4) . 2_655 ?
O1 Hg1 O2 78.3(5) . 6 ?
Hg1 Hg1 O2 108.9(3) 2_655 6 ?
P1 O1 Hg1 133.6(9) . . ?
C6 C1 C2 117.8(18) . . ?
C6 C1 P1 123.0(17) . . ?
C2 C1 P1 119.1(14) . . ?
O1 P1 O2 115.0(8) . . ?
O1 P1 O3 110.0(8) . . ?
O2 P1 O3 109.6(8) . . ?
O1 P1 C1 107.5(8) . . ?
O2 P1 C1 109.9(8) . . ?
O3 P1 C1 104.4(8) . . ?
P1 O3 H3 103(10) . . ?
C13 O4 H4 109.5 . . ?
C6 C5 C4 122(2) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C3 C2 C1 121.8(19) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
P1 O2 Hg1 120.1(8) . 6_556 ?
C7 C8 C9 121(2) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C2 C3 C4 119(2) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 H3A 120.3 . . ?
C5 C4 C3 116.9(18) . . ?
C5 C4 C7 121(2) . . ?
C3 C4 C7 122(2) . . ?
C1 C6 C5 122(2) . . ?
C1 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
C12 C7 C8 117(2) . . ?
C12 C7 C4 122(2) . . ?
C8 C7 C4 121(2) . . ?
C10 C9 C8 120(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120(2) . . ?
C9 C10 C13 119(2) . . ?
C11 C10 C13 121(2) . . ?
C7 C12 C11 124(2) . . ?
C7 C12 H12 118.2 . . ?
C11 C12 H12 118.2 . . ?
O5 C13 O4 125(2) . . ?
O5 C13 C10 121(2) . . ?
O4 C13 C10 114(2) . . ?
C10 C11 C12 118(2) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?

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
Hg1 O1 P1 O2 -67.8(14) . . . . ?
Hg1 O1 P1 O3 56.5(13) . . . . ?
Hg1 O1 P1 C1 169.6(11) . . . . ?
C6 C1 P1 O1 -98.3(19) . . . . ?
C2 C1 P1 O1 80.4(16) . . . . ?
C6 C1 P1 O2 135.9(18) . . . . ?
C2 C1 P1 O2 -45.3(17) . . . . ?
C6 C1 P1 O3 18.4(19) . . . . ?
C2 C1 P1 O3 -162.8(14) . . . . ?
C6 C1 C2 C3 -2(3) . . . . ?
P1 C1 C2 C3 179.4(16) . . . . ?
O1 P1 O2 Hg1 -20.1(11) . . . 6_556 ?
O3 P1 O2 Hg1 -144.6(8) . . . 6_556 ?
C1 P1 O2 Hg1 101.2(9) . . . 6_556 ?
C1 C2 C3 C4 0(3) . . . . ?
C6 C5 C4 C3 -1(3) . . . . ?
C6 C5 C4 C7 174.4(19) . . . . ?
C2 C3 C4 C5 1(3) . . . . ?
C2 C3 C4 C7 -174(2) . . . . ?
C2 C1 C6 C5 2(3) . . . . ?
P1 C1 C6 C5 -179.2(16) . . . . ?
C4 C5 C6 C1 -1(3) . . . . ?
C9 C8 C7 C12 -6(3) . . . . ?
C9 C8 C7 C4 179(2) . . . . ?
C5 C4 C7 C12 8(3) . . . . ?
C3 C4 C7 C12 -177(2) . . . . ?
C5 C4 C7 C8 -178(2) . . . . ?
C3 C4 C7 C8 -2(3) . . . . ?
C7 C8 C9 C10 2(4) . . . . ?
C8 C9 C10 C11 1(4) . . . . ?
C8 C9 C10 C13 -176(2) . . . . ?
C8 C7 C12 C11 7(3) . . . . ?
C4 C7 C12 C11 -178(2) . . . . ?
C9 C10 C13 O5 5(4) . . . . ?
C11 C10 C13 O5 -172(2) . . . . ?
C9 C10 C13 O4 -174(3) . . . . ?
C11 C10 C13 O4 9(4) . . . . ?
C9 C10 C11 C12 0(4) . . . . ?
C13 C10 C11 C12 177(2) . . . . ?
C7 C12 C11 C10 -4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O2 0.89(5) 1.67(10) 2.514(18) 158(21) 6_565
O4 H4 O5 0.84 1.78 2.619(19) 173.5 7_557
C2 H2 O1 0.95 2.49 3.37(2) 153.5 6_556

_refine_diff_density_max         8.072
_refine_diff_density_min         -3.805
_refine_diff_density_rms         0.458


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method water
####################################################################### 
# 
# 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_BPPA_OH_Zn
_database_code_depnum_ccdc_archive 'CCDC 1465332'
_audit_update_record             
;
2016-03-13 deposited with the CCDC.
2016-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 O14 P2 Zn5'
_chemical_formula_sum            'C26 H20 O14 P2 Zn5'
_chemical_formula_weight         945.31

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

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

_cell_length_a                   32.838(12)
_cell_length_b                   5.3763(19)
_cell_length_c                   7.913(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.531(11)
_cell_angle_gamma                90
_cell_volume                     1358.2(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2248
_cell_measurement_theta_min      2.552
_cell_measurement_theta_max      34.387

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.311
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    4.548
_shelx_estimated_absorpt_T_min   0.659
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5016
_exptl_absorpt_correction_T_max  0.7476
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8001
_diffrn_reflns_av_unetI/netI     0.0789
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.552
_diffrn_reflns_theta_max         29.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_point_group_measured_fraction_full 0.883
_reflns_number_total             3360
_reflns_number_gt                2930
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.533
_reflns_Friedel_fraction_max     0.649
_reflns_Friedel_fraction_full    0.737

_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND 3.2 (Crystal Impact, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0302P)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 
;
 Flack x determined using 866 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.050(18)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3360
_refine_ls_number_parameters     220
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.0851
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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
Zn1 Zn 0.03615(2) 0.26293(12) 0.15520(7) 0.00706(15) Uani 1 1 d . . . . .
Zn2 Zn 0.04016(2) 0.74420(13) 0.84943(8) 0.00787(16) Uani 1 1 d . . . . .
Zn3 Zn 0.0000 1.0004(2) 0.5000 0.0083(2) Uani 1 2 d S T P . .
P1 P 0.06199(5) 0.4901(3) 0.52687(17) 0.0063(3) Uani 1 1 d . . . . .
O1 O 0.04510(13) 0.7215(8) 0.6039(5) 0.0058(8) Uani 1 1 d . . . . .
O2 O 0.04594(12) 0.2485(9) 0.5885(5) 0.0097(8) Uani 1 1 d . . . . .
O3 O 0.05136(14) 0.5235(8) 0.3280(5) 0.0099(9) Uani 1 1 d . . . . .
O4 O 0.40566(15) 0.3551(9) 1.0289(6) 0.0190(11) Uani 1 1 d . . . . .
O5 O 0.40662(15) 0.6087(9) 0.8048(6) 0.0144(10) Uani 1 1 d . . . . .
O6 O 0.03068(15) 0.3993(8) -0.0851(5) 0.0090(9) Uani 1 1 d . . . . .
H6 H 0.029(4) 0.32(2) -0.165(13) 0.08(4) Uiso 1 1 d . . . . .
O7 O 0.01008(15) -0.0459(8) 0.2283(6) 0.0094(9) Uani 1 1 d . . . . .
H7 H 0.030(2) -0.135(14) 0.244(9) 0.014 Uiso 1 1 d . U . . .
C1 C 0.11809(19) 0.4882(12) 0.6003(7) 0.0093(11) Uani 1 1 d . . . . .
C2 C 0.1391(2) 0.3016(13) 0.7055(8) 0.0163(15) Uani 1 1 d . . . . .
H2 H 0.1238 0.1733 0.7452 0.020 Uiso 1 1 calc R U . . .
C3 C 0.1825(2) 0.3010(12) 0.7535(8) 0.0165(15) Uani 1 1 d . . . . .
H3 H 0.1962 0.1678 0.8229 0.020 Uiso 1 1 calc R U . . .
C4 C 0.20639(19) 0.4859(13) 0.7046(7) 0.0107(12) Uani 1 1 d . . . . .
C5 C 0.1847(2) 0.6795(13) 0.6016(9) 0.0179(15) Uani 1 1 d . . . . .
H5 H 0.2000 0.8122 0.5669 0.021 Uiso 1 1 calc R U . . .
C6 C 0.1416(2) 0.6797(12) 0.5503(8) 0.0155(15) Uani 1 1 d . . . . .
H6A H 0.1277 0.8117 0.4801 0.019 Uiso 1 1 calc R U . . .
C7 C 0.25323(19) 0.4846(13) 0.7538(7) 0.0102(12) Uani 1 1 d . . . . .
C8 C 0.2752(2) 0.3049(13) 0.8684(8) 0.0181(15) Uani 1 1 d . . . . .
H8 H 0.2601 0.1823 0.9151 0.022 Uiso 1 1 calc R U . . .
C9 C 0.3187(2) 0.3034(12) 0.9145(8) 0.0151(14) Uani 1 1 d . . . . .
H9 H 0.3330 0.1806 0.9926 0.018 Uiso 1 1 calc R U . . .
C10 C 0.34148(19) 0.4812(12) 0.8470(7) 0.0082(11) Uani 1 1 d . . . . .
C11 C 0.3200(2) 0.6606(13) 0.7352(9) 0.0185(15) Uani 1 1 d . . . . .
H11 H 0.3352 0.7835 0.6892 0.022 Uiso 1 1 calc R U . . .
C12 C 0.2768(2) 0.6627(12) 0.6901(9) 0.0177(15) Uani 1 1 d . . . . .
H12 H 0.2627 0.7883 0.6139 0.021 Uiso 1 1 calc R U . . .
C13 C 0.38804(19) 0.4806(12) 0.8959(7) 0.0101(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O3 1.940(4) . ?
Zn1 O6 2.007(4) . ?
Zn1 O5 2.010(5) 4_546 ?
Zn1 O7 2.014(5) . ?
Zn1 O6 2.256(5) 2 ?
Zn1 Zn1 2.9902(15) 2 ?
Zn2 O4 1.909(5) 4_557 ?
Zn2 O6 1.970(4) 1_556 ?
Zn2 O7 1.974(5) 2_566 ?
Zn2 O1 1.991(4) . ?
Zn2 Zn3 3.0944(12) . ?
Zn3 O2 2.013(5) 1_565 ?
Zn3 O2 2.013(5) 2_566 ?
Zn3 O1 2.133(4) . ?
Zn3 O1 2.133(4) 2_556 ?
Zn3 O7 2.264(4) 1_565 ?
Zn3 O7 2.264(4) 2_566 ?
Zn3 Zn2 3.0944(12) 2_556 ?
P1 O2 1.524(5) . ?
P1 O3 1.541(4) . ?
P1 O1 1.544(4) . ?
P1 C1 1.797(6) . ?
O2 Zn3 2.013(4) 1_545 ?
O4 C13 1.270(7) . ?
O4 Zn2 1.909(5) 4_547 ?
O5 C13 1.253(7) . ?
O5 Zn1 2.010(5) 4_556 ?
O6 Zn2 1.970(4) 1_554 ?
O6 Zn1 2.256(5) 2 ?
O6 H6 0.76(11) . ?
O7 Zn2 1.974(5) 2_546 ?
O7 Zn3 2.264(4) 1_545 ?
O7 H7 0.79(8) . ?
C1 C2 1.381(9) . ?
C1 C6 1.398(9) . ?
C2 C3 1.385(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.408(9) . ?
C4 C7 1.496(8) . ?
C5 C6 1.378(10) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9500 . ?
C7 C12 1.397(9) . ?
C7 C8 1.404(9) . ?
C8 C9 1.390(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(9) . ?
C10 C13 1.487(8) . ?
C11 C12 1.381(9) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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 Zn1 O6 110.82(18) . . ?
O3 Zn1 O5 96.31(18) . 4_546 ?
O6 Zn1 O5 99.97(19) . 4_546 ?
O3 Zn1 O7 116.73(18) . . ?
O6 Zn1 O7 128.57(19) . . ?
O5 Zn1 O7 93.40(19) 4_546 . ?
O3 Zn1 O6 90.79(17) . 2 ?
O6 Zn1 O6 77.4(2) . 2 ?
O5 Zn1 O6 172.90(17) 4_546 2 ?
O7 Zn1 O6 83.34(17) . 2 ?
O3 Zn1 Zn1 127.09(13) . 2 ?
O6 Zn1 Zn1 48.98(14) . 2 ?
O5 Zn1 Zn1 131.51(13) 4_546 2 ?
O7 Zn1 Zn1 85.79(13) . 2 ?
O6 Zn1 Zn1 42.14(10) 2 2 ?
O4 Zn2 O6 110.3(2) 4_557 1_556 ?
O4 Zn2 O7 126.2(2) 4_557 2_566 ?
O6 Zn2 O7 116.62(19) 1_556 2_566 ?
O4 Zn2 O1 103.41(19) 4_557 . ?
O6 Zn2 O1 104.64(18) 1_556 . ?
O7 Zn2 O1 89.09(18) 2_566 . ?
O4 Zn2 Zn3 117.61(16) 4_557 . ?
O6 Zn2 Zn3 126.40(13) 1_556 . ?
O7 Zn2 Zn3 46.92(13) 2_566 . ?
O1 Zn2 Zn3 43.14(12) . . ?
O2 Zn3 O2 97.0(3) 1_565 2_566 ?
O2 Zn3 O1 86.30(16) 1_565 . ?
O2 Zn3 O1 175.21(18) 2_566 . ?
O2 Zn3 O1 175.21(18) 1_565 2_556 ?
O2 Zn3 O1 86.30(16) 2_566 2_556 ?
O1 Zn3 O1 90.6(2) . 2_556 ?
O2 Zn3 O7 98.01(16) 1_565 1_565 ?
O2 Zn3 O7 90.37(16) 2_566 1_565 ?
O1 Zn3 O7 92.64(16) . 1_565 ?
O1 Zn3 O7 78.43(15) 2_556 1_565 ?
O2 Zn3 O7 90.37(16) 1_565 2_566 ?
O2 Zn3 O7 98.01(16) 2_566 2_566 ?
O1 Zn3 O7 78.43(15) . 2_566 ?
O1 Zn3 O7 92.64(16) 2_556 2_566 ?
O7 Zn3 O7 167.4(2) 1_565 2_566 ?
O2 Zn3 Zn2 81.72(11) 1_565 . ?
O2 Zn3 Zn2 137.22(11) 2_566 . ?
O1 Zn3 Zn2 39.68(10) . . ?
O1 Zn3 Zn2 98.26(11) 2_556 . ?
O7 Zn3 Zn2 132.31(12) 1_565 . ?
O7 Zn3 Zn2 39.56(12) 2_566 . ?
O2 Zn3 Zn2 137.23(11) 1_565 2_556 ?
O2 Zn3 Zn2 81.72(11) 2_566 2_556 ?
O1 Zn3 Zn2 98.27(11) . 2_556 ?
O1 Zn3 Zn2 39.67(10) 2_556 2_556 ?
O7 Zn3 Zn2 39.56(12) 1_565 2_556 ?
O7 Zn3 Zn2 132.31(12) 2_566 2_556 ?
Zn2 Zn3 Zn2 127.14(5) . 2_556 ?
O2 P1 O3 114.5(2) . . ?
O2 P1 O1 112.2(2) . . ?
O3 P1 O1 107.0(2) . . ?
O2 P1 C1 107.3(3) . . ?
O3 P1 C1 107.5(3) . . ?
O1 P1 C1 108.2(3) . . ?
P1 O1 Zn2 123.6(2) . . ?
P1 O1 Zn3 134.1(2) . . ?
Zn2 O1 Zn3 97.19(17) . . ?
P1 O2 Zn3 137.8(2) . 1_545 ?
P1 O3 Zn1 126.5(3) . . ?
C13 O4 Zn2 140.7(5) . 4_547 ?
C13 O5 Zn1 134.3(4) . 4_556 ?
Zn2 O6 Zn1 127.5(2) 1_554 . ?
Zn2 O6 Zn1 116.5(2) 1_554 2 ?
Zn1 O6 Zn1 88.88(17) . 2 ?
Zn2 O6 H6 108(9) 1_554 . ?
Zn1 O6 H6 123(9) . . ?
Zn1 O6 H6 75(9) 2 . ?
Zn2 O7 Zn1 139.7(2) 2_546 . ?
Zn2 O7 Zn3 93.52(18) 2_546 1_545 ?
Zn1 O7 Zn3 110.38(19) . 1_545 ?
Zn2 O7 H7 107(6) 2_546 . ?
Zn1 O7 H7 99(6) . . ?
Zn3 O7 H7 102(5) 1_545 . ?
C2 C1 C6 118.3(6) . . ?
C2 C1 P1 121.9(5) . . ?
C6 C1 P1 119.8(5) . . ?
C1 C2 C3 120.2(6) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 122.6(6) . . ?
C4 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
C3 C4 C5 116.8(6) . . ?
C3 C4 C7 122.9(6) . . ?
C5 C4 C7 120.3(6) . . ?
C6 C5 C4 121.1(6) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 120.9(6) . . ?
C5 C6 H6A 119.6 . . ?
C1 C6 H6A 119.6 . . ?
C12 C7 C8 117.4(6) . . ?
C12 C7 C4 121.7(6) . . ?
C8 C7 C4 120.9(6) . . ?
C9 C8 C7 121.0(6) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 120.4(6) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 118.9(6) . . ?
C11 C10 C13 120.4(6) . . ?
C9 C10 C13 120.7(6) . . ?
C12 C11 C10 120.6(6) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 121.6(6) . . ?
C11 C12 H12 119.2 . . ?
C7 C12 H12 119.2 . . ?
O5 C13 O4 125.4(6) . . ?
O5 C13 C10 117.3(5) . . ?
O4 C13 C10 117.2(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 P1 O1 Zn2 41.0(3) . . . . ?
O3 P1 O1 Zn2 167.3(3) . . . . ?
C1 P1 O1 Zn2 -77.1(3) . . . . ?
O2 P1 O1 Zn3 -107.4(3) . . . . ?
O3 P1 O1 Zn3 18.9(4) . . . . ?
C1 P1 O1 Zn3 134.5(3) . . . . ?
O3 P1 O2 Zn3 -24.5(5) . . . 1_545 ?
O1 P1 O2 Zn3 97.7(4) . . . 1_545 ?
C1 P1 O2 Zn3 -143.7(4) . . . 1_545 ?
O2 P1 O3 Zn1 -20.0(4) . . . . ?
O1 P1 O3 Zn1 -144.9(3) . . . . ?
C1 P1 O3 Zn1 99.0(4) . . . . ?
O2 P1 C1 C2 -4.9(6) . . . . ?
O3 P1 C1 C2 -128.5(5) . . . . ?
O1 P1 C1 C2 116.3(5) . . . . ?
O2 P1 C1 C6 175.0(5) . . . . ?
O3 P1 C1 C6 51.4(6) . . . . ?
O1 P1 C1 C6 -63.8(6) . . . . ?
C6 C1 C2 C3 -2.6(10) . . . . ?
P1 C1 C2 C3 177.3(5) . . . . ?
C1 C2 C3 C4 2.0(11) . . . . ?
C2 C3 C4 C5 -0.1(10) . . . . ?
C2 C3 C4 C7 -179.1(6) . . . . ?
C3 C4 C5 C6 -1.2(10) . . . . ?
C7 C4 C5 C6 177.9(6) . . . . ?
C4 C5 C6 C1 0.5(11) . . . . ?
C2 C1 C6 C5 1.4(10) . . . . ?
P1 C1 C6 C5 -178.5(5) . . . . ?
C3 C4 C7 C12 174.4(6) . . . . ?
C5 C4 C7 C12 -4.6(9) . . . . ?
C3 C4 C7 C8 -6.5(10) . . . . ?
C5 C4 C7 C8 174.5(6) . . . . ?
C12 C7 C8 C9 -0.7(10) . . . . ?
C4 C7 C8 C9 -179.9(6) . . . . ?
C7 C8 C9 C10 -0.2(10) . . . . ?
C8 C9 C10 C11 0.8(10) . . . . ?
C8 C9 C10 C13 -180.0(6) . . . . ?
C9 C10 C11 C12 -0.5(10) . . . . ?
C13 C10 C11 C12 -179.7(6) . . . . ?
C10 C11 C12 C7 -0.5(11) . . . . ?
C8 C7 C12 C11 1.1(10) . . . . ?
C4 C7 C12 C11 -179.8(7) . . . . ?
Zn1 O5 C13 O4 -21.0(10) 4_556 . . . ?
Zn1 O5 C13 C10 157.3(4) 4_556 . . . ?
Zn2 O4 C13 O5 -9.9(12) 4_547 . . . ?
Zn2 O4 C13 C10 171.9(5) 4_547 . . . ?
C11 C10 C13 O5 -15.5(9) . . . . ?
C9 C10 C13 O5 165.3(6) . . . . ?
C11 C10 C13 O4 162.9(6) . . . . ?
C9 C10 C13 O4 -16.3(9) . . . . ?

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
O6 H6 O2 0.76(11) 2.18(11) 2.860(6) 150(12) 1_554
O6 H6 O7 0.76(11) 2.34(12) 2.845(6) 125(11) 2
O7 H7 O3 0.79(8) 2.03(7) 2.705(6) 144(8) 1_545

_refine_diff_density_max         1.674
_refine_diff_density_min         -1.087
_refine_diff_density_rms         0.166


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method water
####################################################################### 
# 
# 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_CHD_biphenyl
_database_code_depnum_ccdc_archive 'CCDC 1465333'
_audit_update_record             
;
2016-03-13 deposited with the CCDC.
2016-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H11 I O2'
_chemical_formula_sum            'C14 H11 I O2'
_chemical_formula_weight         338.13

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   6.0355(4)
_cell_length_b                   7.2980(4)
_cell_length_c                   27.8833(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1228.18(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9161
_cell_measurement_theta_min      2.791
_cell_measurement_theta_max      37.584

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.829
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.593
_shelx_estimated_absorpt_T_min   0.781
_shelx_estimated_absorpt_T_max   0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7237
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10289
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.791
_diffrn_reflns_theta_max         26.348
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             2381
_reflns_number_gt                2325
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.863
_reflns_Friedel_fraction_max     0.902
_reflns_Friedel_fraction_full    0.906

_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND 3.2 (Crystal Impact, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_refine_special_details          
;
Bruker AXS. (2012). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker AXS. (2012). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker AXS. (2012). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Crystal Impact (2009). DIAMOND. Version3.2.
Crystal Impact GbR, Bonn, Germany.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+1.3301P] 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_abs_structure_details 
;
 Flack x determined using 1036 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.080(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2381
_refine_ls_number_parameters     155
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0687
_refine_ls_wR_factor_gt          0.0681
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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
I1 I 0.96651(6) 0.27649(5) 0.00478(2) 0.04722(16) Uani 1 1 d . . . . .
C1 C 0.8381(10) 0.2632(6) 0.0739(2) 0.0302(11) Uani 1 1 d . . . . .
O1 O 0.4136(11) 0.3040(10) 0.3953(2) 0.0640(16) Uani 1 1 d . . . . .
C2 C 0.6350(11) 0.1828(9) 0.0829(2) 0.0402(13) Uani 1 1 d . . . . .
H2 H 0.5525 0.1310 0.0572 0.048 Uiso 1 1 calc R U . . .
O2 O 0.1033(8) 0.1939(7) 0.36450(19) 0.0503(11) Uani 1 1 d . . . . .
C3 C 0.5511(10) 0.1774(9) 0.1291(3) 0.0372(13) Uani 1 1 d . . . . .
H3 H 0.4104 0.1228 0.1344 0.045 Uiso 1 1 calc R U . . .
C5 C 0.8720(9) 0.3282(8) 0.1584(2) 0.0333(11) Uani 1 1 d . . . . .
H5 H 0.9556 0.3790 0.1840 0.040 Uiso 1 1 calc R U . . .
C4 C 0.6670(8) 0.2498(6) 0.1682(2) 0.0255(10) Uani 1 1 d . . . . .
C6 C 0.9574(10) 0.3343(9) 0.1127(2) 0.0364(12) Uani 1 1 d . . . . .
H6 H 1.0990 0.3874 0.1074 0.044 Uiso 1 1 calc R U . . .
C14 C -0.0037(15) 0.2052(13) 0.4107(4) 0.060(2) Uani 1 1 d . . . . .
H14A H 0.0264 0.3252 0.4251 0.090 Uiso 1 1 calc R U . . .
H14B H 0.0537 0.1085 0.4317 0.090 Uiso 1 1 calc R U . . .
H14C H -0.1639 0.1896 0.4067 0.090 Uiso 1 1 calc R U . . .
C8 C 0.3665(9) 0.1713(7) 0.2277(2) 0.0317(11) Uani 1 1 d . . . . .
H8 H 0.2828 0.1188 0.2023 0.038 Uiso 1 1 calc R U . . .
C13 C 0.3093(10) 0.2497(8) 0.3615(2) 0.0357(12) Uani 1 1 d . . . . .
C10 C 0.3974(10) 0.2443(7) 0.3118(2) 0.0304(11) Uani 1 1 d . . . . .
C9 C 0.2801(9) 0.1698(7) 0.2734(2) 0.0333(11) Uani 1 1 d . . . . .
H9 H 0.1384 0.1171 0.2788 0.040 Uiso 1 1 calc R U . . .
C11 C 0.6045(10) 0.3207(8) 0.3024(2) 0.0362(12) Uani 1 1 d . . . . .
H11 H 0.6879 0.3722 0.3280 0.043 Uiso 1 1 calc R U . . .
C12 C 0.6897(8) 0.3224(8) 0.2566(2) 0.0333(12) Uani 1 1 d . . . . .
H12 H 0.8313 0.3757 0.2513 0.040 Uiso 1 1 calc R U . . .
C7 C 0.5741(9) 0.2480(6) 0.2175(2) 0.0268(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.080(6) . ?
C1 C2 1.382(8) . ?
C1 C6 1.399(9) . ?
O1 C13 1.202(9) . ?
C2 C3 1.384(10) . ?
C2 H2 0.9500 . ?
O2 C13 1.311(8) . ?
O2 C14 1.444(11) . ?
C3 C4 1.400(9) . ?
C3 H3 0.9500 . ?
C5 C6 1.375(9) . ?
C5 C4 1.390(7) . ?
C5 H5 0.9500 . ?
C4 C7 1.484(8) . ?
C6 H6 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C8 C9 1.376(9) . ?
C8 C7 1.402(8) . ?
C8 H8 0.9500 . ?
C13 C10 1.485(9) . ?
C10 C11 1.393(8) . ?
C10 C9 1.394(8) . ?
C9 H9 0.9500 . ?
C11 C12 1.377(8) . ?
C11 H11 0.9500 . ?
C12 C7 1.405(8) . ?
C12 H12 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.3(6) . . ?
C2 C1 I1 121.2(5) . . ?
C6 C1 I1 120.5(4) . . ?
C1 C2 C3 120.3(6) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C13 O2 C14 117.7(6) . . ?
C2 C3 C4 122.1(5) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C6 C5 C4 121.9(5) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C4 C3 116.6(6) . . ?
C5 C4 C7 121.4(5) . . ?
C3 C4 C7 122.0(5) . . ?
C5 C6 C1 120.8(5) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C8 C7 122.0(5) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
O1 C13 O2 123.2(7) . . ?
O1 C13 C10 123.7(6) . . ?
O2 C13 C10 113.1(5) . . ?
C11 C10 C9 118.0(5) . . ?
C11 C10 C13 119.0(5) . . ?
C9 C10 C13 123.0(5) . . ?
C8 C9 C10 121.0(5) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C12 C11 C10 120.8(5) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C7 122.1(5) . . ?
C11 C12 H12 118.9 . . ?
C7 C12 H12 118.9 . . ?
C8 C7 C12 116.1(5) . . ?
C8 C7 C4 122.0(5) . . ?
C12 C7 C4 121.9(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
C6 C1 C2 C3 1.5(9) . . . . ?
I1 C1 C2 C3 -179.2(5) . . . . ?
C1 C2 C3 C4 -0.7(10) . . . . ?
C6 C5 C4 C3 -0.1(8) . . . . ?
C6 C5 C4 C7 -178.5(5) . . . . ?
C2 C3 C4 C5 0.0(9) . . . . ?
C2 C3 C4 C7 178.4(6) . . . . ?
C4 C5 C6 C1 0.9(9) . . . . ?
C2 C1 C6 C5 -1.5(9) . . . . ?
I1 C1 C6 C5 179.1(5) . . . . ?
C14 O2 C13 O1 2.3(10) . . . . ?
C14 O2 C13 C10 -175.9(6) . . . . ?
O1 C13 C10 C11 -5.9(9) . . . . ?
O2 C13 C10 C11 172.2(5) . . . . ?
O1 C13 C10 C9 175.6(7) . . . . ?
O2 C13 C10 C9 -6.2(8) . . . . ?
C7 C8 C9 C10 -0.4(9) . . . . ?
C11 C10 C9 C8 0.1(8) . . . . ?
C13 C10 C9 C8 178.6(5) . . . . ?
C9 C10 C11 C12 0.1(9) . . . . ?
C13 C10 C11 C12 -178.4(5) . . . . ?
C10 C11 C12 C7 -0.1(9) . . . . ?
C9 C8 C7 C12 0.3(8) . . . . ?
C9 C8 C7 C4 -179.9(5) . . . . ?
C11 C12 C7 C8 -0.1(8) . . . . ?
C11 C12 C7 C4 -179.8(5) . . . . ?
C5 C4 C7 C8 179.2(5) . . . . ?
C3 C4 C7 C8 0.9(8) . . . . ?
C5 C4 C7 C12 -1.0(7) . . . . ?
C3 C4 C7 C12 -179.4(5) . . . . ?

_refine_diff_density_max         0.725
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.097


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method water
####################################################################### 
# 
# 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_CHD238
_database_code_depnum_ccdc_archive 'CCDC 1465334'
_audit_update_record             
;
2016-03-13 deposited with the CCDC.
2016-05-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H16 Cd3 O10 P2'
_chemical_formula_sum            'C26 H16 Cd3 O10 P2'
_chemical_formula_weight         887.53

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'
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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   9.3961(7)
_cell_length_b                   9.5450(7)
_cell_length_c                   27.3230(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2450.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9977
_cell_measurement_theta_min      2.982
_cell_measurement_theta_max      32.152

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.406
_exptl_crystal_F_000             1704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.774
_shelx_estimated_absorpt_T_min   0.769
_shelx_estimated_absorpt_T_max   0.874
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.6851

_exptl_absorpt_correction_T_max  0.7465

_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2012)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48627
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.491
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4301
_reflns_number_gt                4281
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.951
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND 3.2 (Crystal Impact, 2009)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_refine_special_details          
;
Bruker AXS. (2012). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker AXS. (2012). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker AXS. (2012). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Crystal Impact (2009). DIAMOND. Version3.2.
Crystal Impact GbR, Bonn, Germany.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0080P)²+37.9472P] 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_abs_structure_details 
;
 Flack x determined using 2031 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4301
_refine_ls_number_parameters     310
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0773
_refine_ls_wR_factor_gt          0.0772
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.127
_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
Cd1 Cd 0.20034(8) 1.14085(7) 0.51714(3) 0.00779(18) Uani 1 1 d . . . . .
P1 P 0.3589(3) 0.9376(3) 0.45952(10) 0.0056(5) Uani 1 1 d . . . . .
O1 O 0.3912(8) 1.0960(8) 0.4627(3) 0.0086(7) Uani 1 1 d . . . . .
C1 C 0.3083(13) 0.9045(12) 0.3972(4) 0.011(2) Uani 1 1 d . . . . .
Cd2 Cd 0.05912(8) 0.74874(8) 0.48962(3) 0.00764(17) Uani 1 1 d . . . . .
P2 P 0.2664(3) 0.4559(3) 0.45110(10) 0.0067(6) Uani 1 1 d . . . . .
O2 O 0.2275(8) 0.9126(7) 0.4925(3) 0.0086(7) Uani 1 1 d . . . . .
C2 C 0.191(2) 0.9730(18) 0.3796(6) 0.039(5) Uani 1 1 d . . . . .
H2 H 0.1358 1.0295 0.4012 0.047 Uiso 1 1 calc R U . . .
Cd3 Cd 0.45898(9) 0.62151(8) 0.50672(3) 0.01015(19) Uani 1 1 d . . . . .
O3 O 0.4861(8) 0.8433(8) 0.4725(3) 0.0086(7) Uani 1 1 d . . . . .
C3 C 0.150(2) 0.961(2) 0.3308(6) 0.051(6) Uani 1 1 d . . . . .
H3 H 0.0705 1.0138 0.3193 0.061 Uiso 1 1 calc R U . . .
O4 O -0.0791(10) 0.8644(12) 0.0850(3) 0.030(3) Uani 1 1 d . . . . .
C4 C 0.2231(17) 0.8744(15) 0.2984(5) 0.0250(14) Uani 1 1 d . . . . .
O5 O 0.1004(12) 0.7169(10) 0.0743(3) 0.029(2) Uani 1 1 d . . . . .
C5 C 0.3343(15) 0.7985(16) 0.3178(5) 0.022(3) Uani 1 1 d . . . . .
H5 H 0.3845 0.7354 0.2972 0.027 Uiso 1 1 calc R U . . .
O6 O 0.2437(8) 0.6089(8) 0.4650(3) 0.0086(7) Uani 1 1 d . . . . .
C6 C 0.3752(16) 0.8109(16) 0.3661(5) 0.024(3) Uani 1 1 d . . . . .
H6 H 0.4505 0.7543 0.3782 0.029 Uiso 1 1 calc R U . . .
O7 O 0.1829(8) 0.3577(8) 0.4842(3) 0.0086(7) Uani 1 1 d . . . . .
C7 C 0.1775(16) 0.8635(14) 0.2464(5) 0.0250(14) Uani 1 1 d . . . . .
O8 O 0.4250(8) 0.4262(8) 0.4570(3) 0.0086(7) Uani 1 1 d . . . . .
C8 C 0.0556(16) 0.9271(17) 0.2303(5) 0.028(3) Uani 1 1 d . . . . .
H8 H -0.0005 0.9799 0.2526 0.034 Uiso 1 1 calc R U . . .
O9 O 0.0895(10) 0.2183(9) 0.0596(3) 0.018(2) Uani 1 1 d . . . . .
C9 C 0.0123(17) 0.9154(16) 0.1809(5) 0.029(4) Uani 1 1 d . . . . .
H9 H -0.0704 0.9632 0.1699 0.035 Uiso 1 1 calc R U . . .
O10 O -0.0340(11) 0.4155(11) 0.0584(3) 0.026(2) Uani 1 1 d . . . . .
C10 C 0.0887(17) 0.8360(16) 0.1492(5) 0.0250(14) Uani 1 1 d . . . . .
C11 C 0.2123(17) 0.7730(19) 0.1648(5) 0.033(4) Uani 1 1 d . . . . .
H11 H 0.2670 0.7182 0.1426 0.040 Uiso 1 1 calc R U . . .
C12 C 0.2567(17) 0.7896(19) 0.2126(5) 0.035(4) Uani 1 1 d . . . . .
H12 H 0.3444 0.7489 0.2225 0.041 Uiso 1 1 calc R U . . .
C13 C 0.0297(15) 0.8054(15) 0.0984(5) 0.021(2) Uani 1 1 d . . . . .
C14 C 0.2232(12) 0.4309(12) 0.3882(4) 0.010(2) Uani 1 1 d . . . . .
C15 C 0.1341(18) 0.5230(16) 0.3634(5) 0.030(4) Uani 1 1 d . . . . .
H15 H 0.0904 0.5979 0.3807 0.036 Uiso 1 1 calc R U . . .
C16 C 0.1084(19) 0.5070(17) 0.3141(5) 0.034(4) Uani 1 1 d . . . . .
H16 H 0.0481 0.5727 0.2982 0.041 Uiso 1 1 calc R U . . .
C17 C 0.1657(14) 0.4012(14) 0.2870(5) 0.016(3) Uani 1 1 d . . . . .
C18 C 0.2465(17) 0.3065(16) 0.3128(5) 0.0250(14) Uani 1 1 d . . . . .
H18 H 0.2833 0.2275 0.2959 0.030 Uiso 1 1 calc R U . . .
C19 C 0.2775(17) 0.3201(15) 0.3625(5) 0.0250(14) Uani 1 1 d . . . . .
H19 H 0.3360 0.2529 0.3784 0.030 Uiso 1 1 calc R U . . .
C20 C 0.1368(15) 0.3852(14) 0.2335(4) 0.019(3) Uani 1 1 d . . . . .
C21 C 0.0485(19) 0.4766(17) 0.2086(5) 0.035(4) Uani 1 1 d . . . . .
H21 H 0.0070 0.5529 0.2257 0.042 Uiso 1 1 calc R U . . .
C22 C 0.0191(18) 0.4597(16) 0.1596(5) 0.029(4) Uani 1 1 d . . . . .
H22 H -0.0430 0.5234 0.1436 0.034 Uiso 1 1 calc R U . . .
C23 C 0.0794(14) 0.3505(15) 0.1335(5) 0.020(3) Uani 1 1 d . . . . .
C24 C 0.1658(19) 0.2570(18) 0.1578(5) 0.035(4) Uani 1 1 d . . . . .
H24 H 0.2059 0.1797 0.1408 0.042 Uiso 1 1 calc R U . . .
C25 C 0.1940(17) 0.2761(18) 0.2069(5) 0.030(4) Uani 1 1 d . . . . .
H25 H 0.2551 0.2116 0.2230 0.036 Uiso 1 1 calc R U . . .
C26 C 0.0447(15) 0.3288(15) 0.0805(5) 0.021(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cd1 O4 2.177(9) 2_575 ?
Cd1 O7 2.263(7) 1_565 ?
Cd1 O2 2.294(7) . ?
Cd1 O3 2.359(8) 4_475 ?
Cd1 O1 2.370(7) . ?
Cd1 O9 2.406(9) 3_565 ?
Cd1 P1 2.909(3) . ?
Cd1 Cd3 3.2202(11) 4_475 ?
P1 O3 1.538(8) . ?
P1 O1 1.545(8) . ?
P1 O2 1.547(8) . ?
P1 C1 1.796(12) . ?
O1 Cd2 2.286(8) 4_575 ?
C1 C2 1.37(2) . ?
C1 C6 1.384(17) . ?
Cd2 O2 2.226(7) . ?
Cd2 O8 2.273(8) 4_465 ?
Cd2 O1 2.286(8) 4_475 ?
Cd2 O6 2.289(8) . ?
Cd2 O9 2.387(9) 2_565 ?
Cd2 O10 2.458(9) 2_565 ?
P2 O7 1.520(8) . ?
P2 O6 1.525(8) . ?
P2 O8 1.526(8) . ?
P2 C14 1.782(11) . ?
P2 Cd3 2.843(3) . ?
C2 C3 1.39(2) . ?
C2 H2 0.9500 . ?
Cd3 O5 2.132(9) 3 ?
Cd3 O7 2.201(7) 4_565 ?
Cd3 O6 2.324(8) . ?
Cd3 O3 2.328(8) . ?
Cd3 O8 2.328(8) . ?
Cd3 O10 2.521(10) 3 ?
Cd3 Cd1 3.2202(11) 4_575 ?
O3 Cd1 2.358(8) 4_575 ?
C3 C4 1.40(2) . ?
C3 H3 0.9500 . ?
O4 C13 1.224(17) . ?
O4 Cd1 2.177(9) 2_574 ?
C4 C5 1.38(2) . ?
C4 C7 1.486(17) . ?
O5 C13 1.261(17) . ?
O5 Cd3 2.132(9) 3_554 ?
C5 C6 1.379(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
O7 Cd3 2.201(7) 4_465 ?
O7 Cd1 2.263(7) 1_545 ?
C7 C8 1.37(2) . ?
C7 C12 1.38(2) . ?
O8 Cd2 2.273(8) 4_565 ?
C8 C9 1.414(19) . ?
C8 H8 0.9500 . ?
O9 C26 1.272(16) . ?
O9 Cd2 2.387(9) 2_564 ?
O9 Cd1 2.406(8) 3_544 ?
C9 C10 1.36(2) . ?
C9 H9 0.9500 . ?
O10 C26 1.263(17) . ?
O10 Cd2 2.458(9) 2_564 ?
O10 Cd3 2.521(10) 3_554 ?
C10 C11 1.38(2) . ?
C10 C13 1.523(18) . ?
C11 C12 1.38(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 C19 1.368(18) . ?
C14 C15 1.390(18) . ?
C15 C16 1.378(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.36(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.375(19) . ?
C17 C20 1.495(17) . ?
C18 C19 1.394(18) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C25 1.38(2) . ?
C20 C21 1.38(2) . ?
C21 C22 1.38(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.38(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.38(2) . ?
C23 C26 1.499(17) . ?
C24 C25 1.38(2) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Cd1 O7 108.8(4) 2_575 1_565 ?
O4 Cd1 O2 106.6(4) 2_575 . ?
O7 Cd1 O2 139.4(3) 1_565 . ?
O4 Cd1 O3 89.7(3) 2_575 4_475 ?
O7 Cd1 O3 71.0(3) 1_565 4_475 ?
O2 Cd1 O3 90.3(3) . 4_475 ?
O4 Cd1 O1 158.0(3) 2_575 . ?
O7 Cd1 O1 88.3(3) 1_565 . ?
O2 Cd1 O1 63.9(3) . . ?
O3 Cd1 O1 109.5(3) 4_475 . ?
O4 Cd1 O9 91.5(3) 2_575 3_565 ?
O7 Cd1 O9 88.3(3) 1_565 3_565 ?
O2 Cd1 O9 110.0(3) . 3_565 ?
O3 Cd1 O9 158.4(3) 4_475 3_565 ?
O1 Cd1 O9 74.7(3) . 3_565 ?
O4 Cd1 P1 135.5(3) 2_575 . ?
O7 Cd1 P1 115.6(2) 1_565 . ?
O2 Cd1 P1 31.90(19) . . ?
O3 Cd1 P1 101.55(19) 4_475 . ?
O1 Cd1 P1 32.01(19) . . ?
O9 Cd1 P1 92.6(2) 3_565 . ?
O4 Cd1 Cd3 73.9(3) 2_575 4_475 ?
O7 Cd1 Cd3 43.08(19) 1_565 4_475 ?
O2 Cd1 Cd3 136.17(19) . 4_475 ?
O3 Cd1 Cd3 46.20(18) 4_475 4_475 ?
O1 Cd1 Cd3 127.21(19) . 4_475 ?
O9 Cd1 Cd3 113.8(2) 3_565 4_475 ?
P1 Cd1 Cd3 141.50(6) . 4_475 ?
O3 P1 O1 114.0(4) . . ?
O3 P1 O2 113.3(4) . . ?
O1 P1 O2 106.0(4) . . ?
O3 P1 C1 108.8(5) . . ?
O1 P1 C1 106.1(5) . . ?
O2 P1 C1 108.3(5) . . ?
O3 P1 Cd1 131.6(3) . . ?
O1 P1 Cd1 54.4(3) . . ?
O2 P1 Cd1 51.6(3) . . ?
C1 P1 Cd1 119.7(4) . . ?
P1 O1 Cd2 142.0(5) . 4_575 ?
P1 O1 Cd1 93.6(4) . . ?
Cd2 O1 Cd1 101.7(3) 4_575 . ?
C2 C1 C6 117.3(12) . . ?
C2 C1 P1 117.5(10) . . ?
C6 C1 P1 125.1(10) . . ?
O2 Cd2 O8 157.5(3) . 4_465 ?
O2 Cd2 O1 92.7(3) . 4_475 ?
O8 Cd2 O1 88.1(3) 4_465 4_475 ?
O2 Cd2 O6 83.2(3) . . ?
O8 Cd2 O6 82.9(3) 4_465 . ?
O1 Cd2 O6 143.7(3) 4_475 . ?
O2 Cd2 O9 107.1(3) . 2_565 ?
O8 Cd2 O9 94.9(3) 4_465 2_565 ?
O1 Cd2 O9 76.6(3) 4_475 2_565 ?
O6 Cd2 O9 139.0(3) . 2_565 ?
O2 Cd2 O10 119.3(3) . 2_565 ?
O8 Cd2 O10 77.2(3) 4_465 2_565 ?
O1 Cd2 O10 126.4(3) 4_475 2_565 ?
O6 Cd2 O10 85.7(3) . 2_565 ?
O9 Cd2 O10 54.3(3) 2_565 2_565 ?
O7 P2 O6 111.7(4) . . ?
O7 P2 O8 109.1(4) . . ?
O6 P2 O8 106.7(4) . . ?
O7 P2 C14 111.9(5) . . ?
O6 P2 C14 109.7(5) . . ?
O8 P2 C14 107.4(5) . . ?
O7 P2 Cd3 110.7(3) . . ?
O6 P2 Cd3 54.7(3) . . ?
O8 P2 Cd3 54.9(3) . . ?
C14 P2 Cd3 137.3(4) . . ?
P1 O2 Cd2 130.9(4) . . ?
P1 O2 Cd1 96.5(3) . . ?
Cd2 O2 Cd1 126.7(3) . . ?
C1 C2 C3 121.3(14) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
O5 Cd3 O7 117.0(4) 3 4_565 ?
O5 Cd3 O6 102.6(4) 3 . ?
O7 Cd3 O6 134.4(3) 4_565 . ?
O5 Cd3 O3 89.3(3) 3 . ?
O7 Cd3 O3 72.6(3) 4_565 . ?
O6 Cd3 O3 86.9(3) . . ?
O5 Cd3 O8 144.2(3) 3 . ?
O7 Cd3 O8 92.3(3) 4_565 . ?
O6 Cd3 O8 63.5(3) . . ?
O3 Cd3 O8 120.6(3) . . ?
O5 Cd3 O10 85.5(4) 3 3 ?
O7 Cd3 O10 87.7(3) 4_565 3 ?
O6 Cd3 O10 118.5(3) . 3 ?
O3 Cd3 O10 154.6(3) . 3 ?
O8 Cd3 O10 74.9(3) . 3 ?
O5 Cd3 P2 122.2(3) 3 . ?
O7 Cd3 P2 120.6(2) 4_565 . ?
O6 Cd3 P2 32.38(19) . . ?
O3 Cd3 P2 111.1(2) . . ?
O8 Cd3 P2 32.42(19) . . ?
O10 Cd3 P2 92.5(2) 3 . ?
O5 Cd3 Cd1 78.9(3) 3 4_575 ?
O7 Cd3 Cd1 44.61(19) 4_565 4_575 ?
O6 Cd3 Cd1 133.83(19) . 4_575 ?
O3 Cd3 Cd1 47.0(2) . 4_575 ?
O8 Cd3 Cd1 135.41(19) . 4_575 ?
O10 Cd3 Cd1 107.6(2) 3 4_575 ?
P2 Cd3 Cd1 152.52(7) . 4_575 ?
P1 O3 Cd3 122.7(4) . . ?
P1 O3 Cd1 138.2(4) . 4_575 ?
Cd3 O3 Cd1 86.8(3) . 4_575 ?
C2 C3 C4 121.2(15) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C13 O4 Cd1 133.0(9) . 2_574 ?
C5 C4 C3 116.3(13) . . ?
C5 C4 C7 123.4(13) . . ?
C3 C4 C7 120.3(13) . . ?
C13 O5 Cd3 126.9(9) . 3_554 ?
C4 C5 C6 122.4(12) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
P2 O6 Cd2 137.5(5) . . ?
P2 O6 Cd3 92.9(4) . . ?
Cd2 O6 Cd3 119.0(3) . . ?
C5 C6 C1 121.1(12) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
P2 O7 Cd3 127.2(4) . 4_465 ?
P2 O7 Cd1 139.7(4) . 1_545 ?
Cd3 O7 Cd1 92.3(3) 4_465 1_545 ?
C8 C7 C12 117.5(12) . . ?
C8 C7 C4 121.2(13) . . ?
C12 C7 C4 121.3(13) . . ?
P2 O8 Cd2 136.0(5) . 4_565 ?
P2 O8 Cd3 92.7(4) . . ?
Cd2 O8 Cd3 106.5(3) 4_565 . ?
C7 C8 C9 120.8(14) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C26 O9 Cd2 93.3(8) . 2_564 ?
C26 O9 Cd1 138.0(9) . 3_544 ?
Cd2 O9 Cd1 97.8(3) 2_564 3_544 ?
C10 C9 C8 120.1(14) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C26 O10 Cd2 90.3(8) . 2_564 ?
C26 O10 Cd3 128.0(9) . 3_554 ?
Cd2 O10 Cd3 95.5(3) 2_564 3_554 ?
C9 C10 C11 119.6(13) . . ?
C9 C10 C13 119.8(13) . . ?
C11 C10 C13 120.3(13) . . ?
C10 C11 C12 119.8(14) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C7 122.0(14) . . ?
C11 C12 H12 119.0 . . ?
C7 C12 H12 119.0 . . ?
O4 C13 O5 126.3(12) . . ?
O4 C13 C10 119.2(13) . . ?
O5 C13 C10 114.4(12) . . ?
C19 C14 C15 117.6(11) . . ?
C19 C14 P2 120.9(10) . . ?
C15 C14 P2 121.5(10) . . ?
C16 C15 C14 120.8(13) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 122.9(14) . . ?
C17 C16 H16 118.5 . . ?
C15 C16 H16 118.5 . . ?
C16 C17 C18 115.3(12) . . ?
C16 C17 C20 122.3(13) . . ?
C18 C17 C20 122.3(12) . . ?
C17 C18 C19 123.6(13) . . ?
C17 C18 H18 118.2 . . ?
C19 C18 H18 118.2 . . ?
C14 C19 C18 119.6(13) . . ?
C14 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C25 C20 C21 116.8(12) . . ?
C25 C20 C17 121.5(12) . . ?
C21 C20 C17 121.7(12) . . ?
C22 C21 C20 121.7(13) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C23 120.5(14) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C24 C23 C22 118.8(13) . . ?
C24 C23 C26 120.3(13) . . ?
C22 C23 C26 120.8(12) . . ?
C23 C24 C25 119.7(14) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C20 C25 C24 122.5(14) . . ?
C20 C25 H25 118.7 . . ?
C24 C25 H25 118.7 . . ?
O10 C26 O9 121.4(12) . . ?
O10 C26 C23 120.0(12) . . ?
O9 C26 C23 118.5(12) . . ?

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
O3 P1 O1 Cd2 -10.8(9) . . . 4_575 ?
O2 P1 O1 Cd2 114.5(7) . . . 4_575 ?
C1 P1 O1 Cd2 -130.5(8) . . . 4_575 ?
Cd1 P1 O1 Cd2 114.3(8) . . . 4_575 ?
O3 P1 O1 Cd1 -125.0(4) . . . . ?
O2 P1 O1 Cd1 0.3(4) . . . . ?
C1 P1 O1 Cd1 115.3(5) . . . . ?
O3 P1 C1 C2 176.2(12) . . . . ?
O1 P1 C1 C2 -60.8(13) . . . . ?
O2 P1 C1 C2 52.6(13) . . . . ?
Cd1 P1 C1 C2 -3.0(14) . . . . ?
O3 P1 C1 C6 -1.0(13) . . . . ?
O1 P1 C1 C6 122.1(12) . . . . ?
O2 P1 C1 C6 -124.5(12) . . . . ?
Cd1 P1 C1 C6 179.9(11) . . . . ?
O3 P1 O2 Cd2 -80.9(6) . . . . ?
O1 P1 O2 Cd2 153.3(5) . . . . ?
C1 P1 O2 Cd2 39.8(7) . . . . ?
Cd1 P1 O2 Cd2 153.6(7) . . . . ?
O3 P1 O2 Cd1 125.5(4) . . . . ?
O1 P1 O2 Cd1 -0.3(5) . . . . ?
C1 P1 O2 Cd1 -113.7(5) . . . . ?
C6 C1 C2 C3 -7(3) . . . . ?
P1 C1 C2 C3 175.3(16) . . . . ?
O1 P1 O3 Cd3 150.6(5) . . . . ?
O2 P1 O3 Cd3 29.2(6) . . . . ?
C1 P1 O3 Cd3 -91.3(6) . . . . ?
Cd1 P1 O3 Cd3 87.7(5) . . . . ?
O1 P1 O3 Cd1 22.4(8) . . . 4_575 ?
O2 P1 O3 Cd1 -99.0(7) . . . 4_575 ?
C1 P1 O3 Cd1 140.5(7) . . . 4_575 ?
Cd1 P1 O3 Cd1 -40.4(8) . . . 4_575 ?
C1 C2 C3 C4 3(3) . . . . ?
C2 C3 C4 C5 2(3) . . . . ?
C2 C3 C4 C7 179.9(19) . . . . ?
C3 C4 C5 C6 -2(3) . . . . ?
C7 C4 C5 C6 179.7(15) . . . . ?
O7 P2 O6 Cd2 -40.2(8) . . . . ?
O8 P2 O6 Cd2 -159.3(6) . . . . ?
C14 P2 O6 Cd2 84.6(8) . . . . ?
Cd3 P2 O6 Cd2 -140.8(8) . . . . ?
O7 P2 O6 Cd3 100.6(4) . . . . ?
O8 P2 O6 Cd3 -18.5(4) . . . . ?
C14 P2 O6 Cd3 -134.6(4) . . . . ?
C4 C5 C6 C1 -2(3) . . . . ?
C2 C1 C6 C5 7(2) . . . . ?
P1 C1 C6 C5 -176.1(12) . . . . ?
O6 P2 O7 Cd3 46.1(7) . . . 4_465 ?
O8 P2 O7 Cd3 163.8(5) . . . 4_465 ?
C14 P2 O7 Cd3 -77.4(7) . . . 4_465 ?
Cd3 P2 O7 Cd3 105.1(5) . . . 4_465 ?
O6 P2 O7 Cd1 -147.1(7) . . . 1_545 ?
O8 P2 O7 Cd1 -29.4(9) . . . 1_545 ?
C14 P2 O7 Cd1 89.4(8) . . . 1_545 ?
Cd3 P2 O7 Cd1 -88.1(7) . . . 1_545 ?
C5 C4 C7 C8 171.6(16) . . . . ?
C3 C4 C7 C8 -6(3) . . . . ?
C5 C4 C7 C12 -9(3) . . . . ?
C3 C4 C7 C12 173.3(18) . . . . ?
O7 P2 O8 Cd2 14.9(8) . . . 4_565 ?
O6 P2 O8 Cd2 135.7(6) . . . 4_565 ?
C14 P2 O8 Cd2 -106.7(7) . . . 4_565 ?
Cd3 P2 O8 Cd2 117.3(7) . . . 4_565 ?
O7 P2 O8 Cd3 -102.4(4) . . . . ?
O6 P2 O8 Cd3 18.5(4) . . . . ?
C14 P2 O8 Cd3 136.1(4) . . . . ?
C12 C7 C8 C9 1(2) . . . . ?
C4 C7 C8 C9 -179.5(15) . . . . ?
C7 C8 C9 C10 3(3) . . . . ?
C8 C9 C10 C11 -3(3) . . . . ?
C8 C9 C10 C13 170.5(15) . . . . ?
C9 C10 C11 C12 1(3) . . . . ?
C13 C10 C11 C12 -173.1(16) . . . . ?
C10 C11 C12 C7 3(3) . . . . ?
C8 C7 C12 C11 -4(3) . . . . ?
C4 C7 C12 C11 176.9(16) . . . . ?
Cd1 O4 C13 O5 -2(2) 2_574 . . . ?
Cd1 O4 C13 C10 178.7(10) 2_574 . . . ?
Cd3 O5 C13 O4 -9(2) 3_554 . . . ?
Cd3 O5 C13 C10 170.4(9) 3_554 . . . ?
C9 C10 C13 O4 7(2) . . . . ?
C11 C10 C13 O4 -178.7(15) . . . . ?
C9 C10 C13 O5 -171.6(14) . . . . ?
C11 C10 C13 O5 2(2) . . . . ?
O7 P2 C14 C19 -77.6(12) . . . . ?
O6 P2 C14 C19 157.8(11) . . . . ?
O8 P2 C14 C19 42.1(12) . . . . ?
Cd3 P2 C14 C19 98.9(11) . . . . ?
O7 P2 C14 C15 102.7(12) . . . . ?
O6 P2 C14 C15 -22.0(13) . . . . ?
O8 P2 C14 C15 -137.6(12) . . . . ?
Cd3 P2 C14 C15 -80.9(13) . . . . ?
C19 C14 C15 C16 -4(2) . . . . ?
P2 C14 C15 C16 176.2(14) . . . . ?
C14 C15 C16 C17 1(3) . . . . ?
C15 C16 C17 C18 3(3) . . . . ?
C15 C16 C17 C20 -180.0(16) . . . . ?
C16 C17 C18 C19 -4(2) . . . . ?
C20 C17 C18 C19 178.7(14) . . . . ?
C15 C14 C19 C18 2(2) . . . . ?
P2 C14 C19 C18 -177.4(12) . . . . ?
C17 C18 C19 C14 2(2) . . . . ?
C16 C17 C20 C25 -179.0(15) . . . . ?
C18 C17 C20 C25 -2(2) . . . . ?
C16 C17 C20 C21 -1(2) . . . . ?
C18 C17 C20 C21 176.1(15) . . . . ?
C25 C20 C21 C22 0(2) . . . . ?
C17 C20 C21 C22 -178.3(15) . . . . ?
C20 C21 C22 C23 -1(3) . . . . ?
C21 C22 C23 C24 2(2) . . . . ?
C21 C22 C23 C26 178.2(15) . . . . ?
C22 C23 C24 C25 -2(2) . . . . ?
C26 C23 C24 C25 -178.3(15) . . . . ?
C21 C20 C25 C24 0(2) . . . . ?
C17 C20 C25 C24 178.2(15) . . . . ?
C23 C24 C25 C20 1(3) . . . . ?
Cd2 O10 C26 O9 8.8(13) 2_564 . . . ?
Cd3 O10 C26 O9 -88.4(15) 3_554 . . . ?
Cd2 O10 C26 C23 -167.3(11) 2_564 . . . ?
Cd3 O10 C26 C23 95.5(13) 3_554 . . . ?
Cd2 O9 C26 O10 -9.1(13) 2_564 . . . ?
Cd1 O9 C26 O10 96.4(16) 3_544 . . . ?
Cd2 O9 C26 C23 167.1(11) 2_564 . . . ?
Cd1 O9 C26 C23 -87.5(15) 3_544 . . . ?
C24 C23 C26 O10 -179.5(14) . . . . ?
C22 C23 C26 O10 4(2) . . . . ?
C24 C23 C26 O9 4(2) . . . . ?
C22 C23 C26 O9 -172.1(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C15 H15 O8 0.95 2.61 3.262(17) 126.0 4_465

_refine_diff_density_max         1.729
_refine_diff_density_min         -2.154
_refine_diff_density_rms         0.178


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method water
