# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_SnHOPO
_database_code_depnum_ccdc_archive 'CCDC 1586746'
_audit_update_record             
;
2017-11-20 deposited with the CCDC.
2018-01-25 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_SnHOPO              
;
PROBLEM: Hirshfeld Test Diff for    C7     --  C8      ..        8.0 s.u.  
RESPONSE: There is likely some minor disorder in these atoms but it could not be acceptably modeled. 
;
_vrf_PLAT306_SnHOPO              
;
PROBLEM: Isolated Oxygen Atom (H-atoms Missing ?) .......        O8W Check 
RESPONSE: No H atom can be modeled at an acceptable distance. The missing H atom is included in the reported formula, leading to many of the G-level alerts.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'Sn(1,2-HOPO) trihydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         '(C34 H34 N8 O12 Sn), 3(H2 O)'
_chemical_formula_sum            'C34 H40 N8 O15 Sn'
_chemical_formula_weight         919.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0040 0.0020 'Calculated using XDISP in WinGX (Farrugia, 1999)'
H H 0.0000 0.0000 'Calculated using XDISP in WinGX (Farrugia, 1999)'
N N 0.0076 0.0040 'Calculated using XDISP in WinGX (Farrugia, 1999)'
O O 0.0133 0.0074 'Calculated using XDISP in WinGX (Farrugia, 1999)'
Sn Sn -0.4788 1.6683 'Calculated using XDISP in WinGX (Farrugia, 1999)'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

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

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

_cell_length_a                   16.0345(7)
_cell_length_b                   17.0024(7)
_cell_length_c                   13.3898(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3650.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9817
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      40.22

_exptl_crystal_description       shard
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_F_000             1880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.938
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6936
_exptl_absorpt_correction_T_max  0.7479
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7749
_diffrn_radiation_type           synchrotron
_diffrn_source                   'Advanced Light Source, station 11.3.1'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_measurement_device_type  'Bruker D8 with PHOTON 100 detector'
_diffrn_measurement_method       'phi and omega shutterless scans'
_diffrn_detector_area_resol_mean 10.42
_diffrn_reflns_number            31453
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.525
_diffrn_reflns_theta_max         40.220
_diffrn_reflns_theta_full        27.71
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             8824
_reflns_number_gt                7861
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.989

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

_computing_data_collection       'Bruker APEX3 Bruker, Madison, WI'
_computing_cell_refinement       'SAINT V8.37A Bruker, Madison, WI'
_computing_data_reduction        'SAINT V8.37A Bruker, Madison, WI'
_computing_structure_solution    'SHELXT-2014/4 Bruker, Madison, WI'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_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)+(0.0393P)²+0.8315P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'intrinsic phasing'
_atom_sites_solution_secondary   diffmap
_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 3278 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         8824
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0765
_refine_ls_wR_factor_gt          0.0733
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.51809(14) 0.35715(15) 0.46858(19) 0.0221(5) Uani 1 1 d . . . . .
C2 C 0.54001(18) 0.3713(2) 0.5691(2) 0.0295(5) Uani 1 1 d . . . . .
H2 H 0.5438 0.4236 0.5935 0.035 Uiso 1 1 calc R U . . .
C3 C 0.5558(2) 0.3087(2) 0.6314(2) 0.0346(6) Uani 1 1 d . . . . .
H3 H 0.5707 0.3179 0.6990 0.042 Uiso 1 1 calc R U . . .
C4 C 0.55026(19) 0.23209(19) 0.5963(2) 0.0320(6) Uani 1 1 d . . . . .
H4 H 0.5617 0.1893 0.6397 0.038 Uiso 1 1 calc R U . . .
C5 C 0.52824(16) 0.21823(16) 0.4992(2) 0.0250(5) Uani 1 1 d . . . . .
C6 C 0.51584(15) 0.13651(15) 0.4575(2) 0.0265(5) Uani 1 1 d . . . . .
C7 C 0.5734(2) 0.02446(19) 0.3669(3) 0.0388(7) Uani 1 1 d . . . . .
H7A H 0.5329 -0.0058 0.4073 0.047 Uiso 1 1 calc R U . . .
H7B H 0.6283 -0.0017 0.3732 0.047 Uiso 1 1 calc R U . . .
C8 C 0.5464(2) 0.0217(2) 0.2577(4) 0.0512(9) Uani 1 1 d . . . . .
H8A H 0.5703 0.0677 0.2226 0.061 Uiso 1 1 calc R U . . .
H8B H 0.5699 -0.0262 0.2266 0.061 Uiso 1 1 calc R U . . .
C9 C 0.65770(16) 0.14689(16) 0.3879(2) 0.0253(5) Uani 1 1 d . . . . .
H9A H 0.6458 0.2039 0.3833 0.030 Uiso 1 1 calc R U . . .
H9B H 0.6803 0.1295 0.3228 0.030 Uiso 1 1 calc R U . . .
C10 C 0.72312(17) 0.13287(18) 0.4692(2) 0.0310(6) Uani 1 1 d . . . . .
H10A H 0.7005 0.1503 0.5344 0.037 Uiso 1 1 calc R U . . .
H10B H 0.7349 0.0758 0.4739 0.037 Uiso 1 1 calc R U . . .
C11 C 0.80406(17) 0.17681(17) 0.4481(3) 0.0310(6) Uani 1 1 d . . . . .
H11A H 0.8438 0.1680 0.5036 0.037 Uiso 1 1 calc R U . . .
H11B H 0.8296 0.1563 0.3861 0.037 Uiso 1 1 calc R U . . .
C12 C 0.77899(14) 0.29415(16) 0.3480(2) 0.0241(4) Uani 1 1 d . . . . .
C13 C 0.75204(12) 0.37857(17) 0.3480(2) 0.0226(4) Uani 1 1 d . . . . .
C14 C 0.80041(17) 0.43898(18) 0.3824(2) 0.0294(5) Uani 1 1 d . . . . .
H14 H 0.8504 0.4284 0.4181 0.035 Uiso 1 1 calc R U . . .
C15 C 0.77550(18) 0.51683(18) 0.3646(2) 0.0316(6) Uani 1 1 d . . . . .
H15 H 0.8090 0.5591 0.3880 0.038 Uiso 1 1 calc R U . . .
C16 C 0.70358(17) 0.53231(16) 0.3139(2) 0.0268(5) Uani 1 1 d . . . . .
H16 H 0.6887 0.5852 0.2994 0.032 Uiso 1 1 calc R U . . .
C17 C 0.65103(15) 0.47019(14) 0.2828(2) 0.0212(4) Uani 1 1 d . . . . .
N1 N 0.51128(12) 0.28082(12) 0.43853(15) 0.0197(4) Uani 1 1 d . . . . .
N2 N 0.67824(12) 0.39559(12) 0.30112(16) 0.0199(4) Uani 1 1 d . . . . .
N3 N 0.57993(14) 0.10454(14) 0.40836(19) 0.0265(4) Uani 1 1 d . . . . .
N4 N 0.78800(14) 0.26115(14) 0.43733(19) 0.0266(4) Uani 1 1 d . . . . .
H4A H 0.7842 0.2906 0.4912 0.032 Uiso 1 1 calc R U . . .
O1 O 0.50312(17) 0.41058(9) 0.40304(12) 0.0238(3) Uani 1 1 d . . . . .
O2 O 0.48572(10) 0.26756(10) 0.34388(13) 0.0210(4) Uani 1 1 d . . . . .
O3 O 0.62717(10) 0.33592(10) 0.27354(14) 0.0223(4) Uani 1 1 d . . . . .
O4 O 0.58031(10) 0.47772(9) 0.24050(19) 0.0230(4) Uani 1 1 d . . . . .
O5 O 0.44920(14) 0.10295(14) 0.47377(19) 0.0368(5) Uani 1 1 d . . . . .
O6 O 0.79259(13) 0.26041(14) 0.26854(15) 0.0330(5) Uani 1 1 d . . . . .
O7W O 0.68358(16) 0.19966(14) 0.13611(19) 0.0343(5) Uani 1 1 d . . . . .
O8W O 0.3692(2) 0.5000 0.5000 0.0517(10) Uani 1 2 d S T P . .
Sn1 Sn 0.5000 0.37384(2) 0.2500 0.01570(5) Uani 1 2 d S T P . .
H7WA H 0.716(3) 0.221(2) 0.181(3) 0.034(10) Uiso 1 1 d . . . . .
H7WB H 0.633(3) 0.208(3) 0.149(4) 0.054(14) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.286(3) . ?
C1 N1 1.363(3) . ?
C1 C2 1.412(4) . ?
C2 C3 1.376(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.367(4) . ?
C4 H4 0.9500 . ?
C5 N1 1.366(3) . ?
C5 C6 1.511(4) . ?
C6 O5 1.231(3) . ?
C6 N3 1.336(4) . ?
C7 N3 1.474(4) . ?
C7 C8 1.527(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C8 1.501(7) 3_655 ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N3 1.466(3) . ?
C9 C10 1.530(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.524(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N4 1.464(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O6 1.229(3) . ?
C12 N4 1.329(4) . ?
C12 C13 1.499(4) . ?
C13 C14 1.367(4) . ?
C13 N2 1.370(3) . ?
C14 C15 1.403(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.364(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.414(3) . ?
C16 H16 0.9500 . ?
C17 O4 1.274(3) . ?
C17 N2 1.364(3) . ?
N1 O2 1.351(3) . ?
N2 O3 1.355(3) . ?
N4 H4A 0.8800 . ?
O1 Sn1 2.1429(16) . ?
O2 Sn1 2.2130(17) . ?
O3 Sn1 2.1617(17) . ?
O4 Sn1 2.1896(15) . ?
O7W H7WA 0.87(4) . ?
O7W H7WB 0.84(5) . ?
Sn1 O1 2.1428(16) 3_655 ?
Sn1 O3 2.1617(17) 3_655 ?
Sn1 O4 2.1896(15) 3_655 ?
Sn1 O2 2.2130(17) 3_655 ?

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 C1 N1 117.1(2) . . ?
O1 C1 C2 125.2(3) . . ?
N1 C1 C2 117.6(2) . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
N1 C5 C4 118.9(3) . . ?
N1 C5 C6 118.0(2) . . ?
C4 C5 C6 123.0(2) . . ?
O5 C6 N3 124.5(3) . . ?
O5 C6 C5 118.4(3) . . ?
N3 C6 C5 117.1(2) . . ?
N3 C7 C8 114.1(3) . . ?
N3 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
N3 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C8 C8 C7 114.4(5) 3_655 . ?
C8 C8 H8A 108.7 3_655 . ?
C7 C8 H8A 108.7 . . ?
C8 C8 H8B 108.7 3_655 . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
N3 C9 C10 112.0(2) . . ?
N3 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
N3 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 112.1(2) . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
N4 C11 C10 110.4(2) . . ?
N4 C11 H11A 109.6 . . ?
C10 C11 H11A 109.6 . . ?
N4 C11 H11B 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
O6 C12 N4 124.3(3) . . ?
O6 C12 C13 119.8(3) . . ?
N4 C12 C13 115.9(3) . . ?
C14 C13 N2 119.1(3) . . ?
C14 C13 C12 123.8(2) . . ?
N2 C13 C12 116.8(2) . . ?
C13 C14 C15 119.3(2) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
O4 C17 N2 117.3(2) . . ?
O4 C17 C16 125.9(2) . . ?
N2 C17 C16 116.8(2) . . ?
O2 N1 C1 117.39(19) . . ?
O2 N1 C5 119.2(2) . . ?
C1 N1 C5 123.4(2) . . ?
O3 N2 C17 117.00(19) . . ?
O3 N2 C13 119.2(2) . . ?
C17 N2 C13 123.7(2) . . ?
C6 N3 C9 123.1(2) . . ?
C6 N3 C7 120.5(2) . . ?
C9 N3 C7 116.3(2) . . ?
C12 N4 C11 121.4(3) . . ?
C12 N4 H4A 119.3 . . ?
C11 N4 H4A 119.3 . . ?
C1 O1 Sn1 116.82(15) . . ?
N1 O2 Sn1 111.43(13) . . ?
N2 O3 Sn1 112.74(13) . . ?
C17 O4 Sn1 114.62(15) . . ?
H7WA O7W H7WB 111(4) . . ?
O1 Sn1 O1 146.10(8) 3_655 . ?
O1 Sn1 O3 104.38(9) 3_655 . ?
O1 Sn1 O3 85.73(8) . . ?
O1 Sn1 O3 85.73(8) 3_655 3_655 ?
O1 Sn1 O3 104.38(9) . 3_655 ?
O3 Sn1 O3 145.30(9) . 3_655 ?
O1 Sn1 O4 78.85(9) 3_655 3_655 ?
O1 Sn1 O4 73.92(8) . 3_655 ?
O3 Sn1 O4 141.89(6) . 3_655 ?
O3 Sn1 O4 72.20(6) 3_655 3_655 ?
O1 Sn1 O4 73.92(8) 3_655 . ?
O1 Sn1 O4 78.85(9) . . ?
O3 Sn1 O4 72.20(6) . . ?
O3 Sn1 O4 141.89(6) 3_655 . ?
O4 Sn1 O4 72.45(9) 3_655 . ?
O1 Sn1 O2 141.15(6) 3_655 . ?
O1 Sn1 O2 72.38(6) . . ?
O3 Sn1 O2 76.78(6) . . ?
O3 Sn1 O2 75.03(6) 3_655 . ?
O4 Sn1 O2 124.39(7) 3_655 . ?
O4 Sn1 O2 138.81(7) . . ?
O1 Sn1 O2 72.38(6) 3_655 3_655 ?
O1 Sn1 O2 141.15(6) . 3_655 ?
O3 Sn1 O2 75.03(6) . 3_655 ?
O3 Sn1 O2 76.78(6) 3_655 3_655 ?
O4 Sn1 O2 138.81(7) 3_655 3_655 ?
O4 Sn1 O2 124.39(7) . 3_655 ?
O2 Sn1 O2 70.53(9) . 3_655 ?

_refine_diff_density_max         1.680
_refine_diff_density_min         -0.908
_refine_diff_density_rms         0.086


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
