# Electronic Supplementary Material (ESI) for ChemComm.
# 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. 
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data_zr_sq
_database_code_depnum_ccdc_archive 'CCDC 1502488'
_audit_update_record             
;
2016-09-04 deposited with the CCDC.
2016-12-19 downloaded from the CCDC.
;
_audit_creation_date             2016-08-17
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.26 svn.r3321 for OlexSys, GUI svn.r5206)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H20 O12 P4 Si Zr'
_chemical_formula_sum            'C24 H20 N0 O12 P4 Si Zr'
_chemical_formula_weight         743.59
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zr Zr -0.1862 2.2449 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.9688(2)
_cell_length_b                   19.2157(4)
_cell_length_c                   14.5392(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.702(2)
_cell_angle_gamma                90
_cell_volume                     2745.26(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5132
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.22
_cell_measurement_theta_min      3.85
_shelx_estimated_absorpt_T_max   0.522
_shelx_estimated_absorpt_T_min   0.263
_exptl_absorpt_coefficient_mu    6.500
_exptl_absorpt_correction_T_max  0.522
_exptl_absorpt_correction_T_min  0.263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10653
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.217
_diffrn_reflns_theta_min         3.848
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4030
_reflns_number_total             5132
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         2.186
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.127
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5132
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0893P)²+1.8272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1364
_refine_ls_wR_factor_ref         0.1507
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6A), C8(H8), C9(H9), C11(H11), C12(H12A),
 C14(H14), C15(H15), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O6(H6), O12(H12), O9(H9A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
Zr1 Zr 0.74982(2) 0.54975(2) 0.49874(2) 0.01610(14) Uani 1 1 d . . . . .
Si1 Si 0.26115(9) 0.89556(6) 0.49988(6) 0.0221(2) Uani 1 1 d . . . . .
P1 P -0.01975(9) 1.05923(5) 0.12781(6) 0.0184(2) Uani 1 1 d . . . . .
P2 P -0.18317(10) 0.69504(5) 0.64500(7) 0.0269(2) Uani 1 1 d . . . . .
P3 P 0.67869(11) 0.68638(5) 0.34157(7) 0.0269(2) Uani 1 1 d . . . . .
P4 P 0.52163(9) 1.06219(5) 0.87352(6) 0.0182(2) Uani 1 1 d . . . . .
O1 O -0.0425(3) 1.13736(15) 0.1467(2) 0.0286(6) Uani 1 1 d . . . . .
H1 H 0.0289 1.1587 0.1472 0.043 Uiso 1 1 calc GR . . . .
O2 O 0.0781(3) 1.05098(14) 0.05973(19) 0.0246(6) Uani 1 1 d . . . . .
O3 O -0.1556(3) 1.02543(14) 0.09159(17) 0.0211(5) Uani 1 1 d . . . . .
O4 O -0.3253(3) 0.72463(17) 0.6325(2) 0.0363(7) Uani 1 1 d . . . . .
O6 O -0.1282(3) 0.67674(17) 0.7493(2) 0.0356(7) Uani 1 1 d . . . . .
H6 H -0.1476 0.7081 0.7829 0.053 Uiso 1 1 calc GR . . . .
O7 O 0.8204(3) 0.71582(16) 0.3491(2) 0.0343(7) Uani 1 1 d . . . . .
O8 O 0.6709(3) 0.61851(15) 0.3949(2) 0.0294(6) Uani 1 1 d . . . . .
O10 O 0.4182(3) 1.05308(14) 0.93803(19) 0.0241(6) Uani 1 1 d . . . . .
O11 O 0.6582(3) 1.03012(14) 0.91234(17) 0.0209(5) Uani 1 1 d . . . . .
O12 O 0.5430(3) 1.14126(14) 0.8580(2) 0.0288(6) Uani 1 1 d . . . . .
H12 H 0.4727 1.1624 0.8618 0.043 Uiso 1 1 calc GR . . . .
C1 C 0.1812(4) 0.9481(2) 0.3957(3) 0.0258(8) Uani 1 1 d . . . . .
C2 C 0.1511(5) 1.0184(2) 0.3975(3) 0.0355(9) Uani 1 1 d . . . . .
H2 H 0.1731 1.0429 0.4532 0.043 Uiso 1 1 calc R . . . .
C3 C 0.0888(5) 1.0533(2) 0.3177(3) 0.0337(9) Uani 1 1 d . . . . .
H3 H 0.0686 1.1004 0.3206 0.040 Uiso 1 1 calc R . . . .
C4 C 0.0569(4) 1.0178(2) 0.2342(2) 0.0219(7) Uani 1 1 d . . . . .
C5 C 0.0907(5) 0.9474(2) 0.2299(3) 0.0404(11) Uani 1 1 d . . . . .
H5 H 0.0715 0.9233 0.1737 0.048 Uiso 1 1 calc R . . . .
C6 C 0.1529(5) 0.9139(2) 0.3102(3) 0.0395(10) Uani 1 1 d . . . . .
H6A H 0.1764 0.8673 0.3069 0.047 Uiso 1 1 calc R . . . .
C7 C 0.1283(4) 0.8420(2) 0.5438(3) 0.0272(8) Uani 1 1 d . . . . .
C8 C -0.0053(5) 0.8394(3) 0.4993(3) 0.0370(9) Uani 1 1 d . . . . .
H8 H -0.0321 0.8663 0.4461 0.044 Uiso 1 1 calc R . . . .
C9 C -0.1011(5) 0.7975(3) 0.5323(3) 0.0383(10) Uani 1 1 d . . . . .
H9 H -0.1909 0.7978 0.5018 0.046 Uiso 1 1 calc R . . . .
C10 C -0.0639(4) 0.7553(2) 0.6099(3) 0.0287(8) Uani 1 1 d . . . . .
C11 C 0.0702(5) 0.7593(3) 0.6565(4) 0.0448(11) Uani 1 1 d . . . . .
H11 H 0.0970 0.7325 0.7097 0.054 Uiso 1 1 calc R . . . .
C12 C 0.1636(5) 0.8022(3) 0.6252(3) 0.0451(12) Uani 1 1 d . . . . .
H12A H 0.2516 0.8048 0.6586 0.054 Uiso 1 1 calc R . . . .
C13 C 0.3857(4) 0.8348(2) 0.4582(3) 0.0266(8) Uani 1 1 d . . . . .
C14 C 0.3655(5) 0.7628(3) 0.4557(4) 0.0463(12) Uani 1 1 d . . . . .
H14 H 0.2917 0.7442 0.4788 0.056 Uiso 1 1 calc R . . . .
C15 C 0.4536(5) 0.7183(3) 0.4194(4) 0.0475(12) Uani 1 1 d . . . . .
H15 H 0.4381 0.6706 0.4178 0.057 Uiso 1 1 calc R . . . .
C16 C 0.5650(4) 0.7456(2) 0.3854(3) 0.0300(8) Uani 1 1 d . . . . .
C17 C 0.5850(5) 0.8154(2) 0.3851(3) 0.0359(9) Uani 1 1 d . . . . .
H17 H 0.6576 0.8335 0.3602 0.043 Uiso 1 1 calc R . . . .
C18 C 0.4976(5) 0.8600(2) 0.4218(3) 0.0366(9) Uani 1 1 d . . . . .
H18 H 0.5140 0.9077 0.4221 0.044 Uiso 1 1 calc R . . . .
C19 C 0.3434(4) 0.95138(19) 0.5991(3) 0.0239(8) Uani 1 1 d . . . . .
C20 C 0.4836(4) 0.9499(2) 0.6333(3) 0.0315(9) Uani 1 1 d . . . . .
H20 H 0.5411 0.9259 0.6002 0.038 Uiso 1 1 calc R . . . .
C21 C 0.5388(4) 0.9839(2) 0.7162(3) 0.0313(8) Uani 1 1 d . . . . .
H21 H 0.6316 0.9813 0.7390 0.038 Uiso 1 1 calc R . . . .
C22 C 0.4538(4) 1.0216(2) 0.7643(2) 0.0225(7) Uani 1 1 d . . . . .
C23 C 0.3164(4) 1.0265(2) 0.7296(3) 0.0304(8) Uani 1 1 d . . . . .
H23 H 0.2602 1.0530 0.7608 0.036 Uiso 1 1 calc R . . . .
C24 C 0.2624(4) 0.9918(2) 0.6482(3) 0.0321(9) Uani 1 1 d . . . . .
H24 H 0.1697 0.9955 0.6255 0.039 Uiso 1 1 calc R . . . .
O5 O -0.1736(3) 0.62781(15) 0.5894(2) 0.0295(6) Uani 1 1 d . . . . .
O9 O 0.6171(4) 0.67163(17) 0.2377(2) 0.0378(7) Uani 1 1 d . . . . .
H9A H 0.6326 0.7047 0.2054 0.057 Uiso 1 1 calc GR . . . .


_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
Zr1 O2 2.039(3) 2_645 ?
Zr1 O3 2.090(3) 4_676 ?
Zr1 O8 2.060(3) . ?
Zr1 O10 2.043(3) 2_646 ?
Zr1 O11 2.093(3) 4_575 ?
Zr1 O5 2.057(3) 1_655 ?
Si1 C1 1.881(4) . ?
Si1 C7 1.872(4) . ?
Si1 C13 1.878(4) . ?
Si1 C19 1.872(4) . ?
P1 O1 1.550(3) . ?
P1 O2 1.511(3) . ?
P1 O3 1.514(3) . ?
P1 C4 1.792(4) . ?
P2 O4 1.509(3) . ?
P2 O6 1.563(3) . ?
P2 C10 1.795(4) . ?
P2 O5 1.536(3) . ?
P3 O7 1.508(3) . ?
P3 O8 1.525(3) . ?
P3 C16 1.797(4) . ?
P3 O9 1.558(3) . ?
P4 O10 1.517(3) . ?
P4 O11 1.514(3) . ?
P4 O12 1.556(3) . ?
P4 C22 1.796(4) . ?
O2 Zr1 2.039(3) 2_655 ?
O3 Zr1 2.090(3) 4_475 ?
O10 Zr1 2.043(3) 2_656 ?
O11 Zr1 2.093(3) 4_576 ?
C1 C2 1.386(6) . ?
C1 C6 1.393(6) . ?
C2 C3 1.392(6) . ?
C3 C4 1.382(5) . ?
C4 C5 1.399(6) . ?
C5 C6 1.384(6) . ?
C7 C8 1.380(6) . ?
C7 C12 1.404(6) . ?
C8 C9 1.394(6) . ?
C9 C10 1.388(6) . ?
C10 C11 1.395(6) . ?
C11 C12 1.377(6) . ?
C13 C14 1.397(7) . ?
C13 C18 1.401(6) . ?
C14 C15 1.392(7) . ?
C15 C16 1.393(7) . ?
C16 C17 1.355(6) . ?
C17 C18 1.392(6) . ?
C19 C20 1.403(6) . ?
C19 C24 1.400(6) . ?
C20 C21 1.400(6) . ?
C21 C22 1.390(6) . ?
C22 C23 1.381(6) . ?
C23 C24 1.386(6) . ?
O5 Zr1 2.057(3) 1_455 ?

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 Zr1 O3 87.56(10) 2_645 4_676 ?
O2 Zr1 O8 86.04(11) 2_645 . ?
O2 Zr1 O10 176.79(11) 2_645 2_646 ?
O2 Zr1 O11 94.05(10) 2_645 4_575 ?
O2 Zr1 O5 90.64(11) 2_645 1_655 ?
O3 Zr1 O11 89.11(12) 4_676 4_575 ?
O8 Zr1 O3 172.52(11) . 4_676 ?
O8 Zr1 O11 87.49(11) . 4_575 ?
O10 Zr1 O3 92.63(10) 2_646 4_676 ?
O10 Zr1 O8 93.98(11) 2_646 . ?
O10 Zr1 O11 89.16(10) 2_646 4_575 ?
O10 Zr1 O5 86.15(11) 2_646 1_655 ?
O5 Zr1 O3 90.68(12) 1_655 4_676 ?
O5 Zr1 O8 93.25(13) 1_655 . ?
O5 Zr1 O11 175.29(10) 1_655 4_575 ?
C7 Si1 C1 109.93(19) . . ?
C7 Si1 C13 108.2(2) . . ?
C13 Si1 C1 106.70(18) . . ?
C19 Si1 C1 112.58(19) . . ?
C19 Si1 C7 107.20(18) . . ?
C19 Si1 C13 112.17(19) . . ?
O1 P1 C4 109.36(17) . . ?
O2 P1 O1 110.34(16) . . ?
O2 P1 O3 111.43(16) . . ?
O2 P1 C4 106.88(17) . . ?
O3 P1 O1 109.16(16) . . ?
O3 P1 C4 109.63(16) . . ?
O4 P2 O6 111.77(18) . . ?
O4 P2 C10 112.1(2) . . ?
O4 P2 O5 113.18(17) . . ?
O6 P2 C10 106.25(19) . . ?
O5 P2 O6 106.19(18) . . ?
O5 P2 C10 106.89(18) . . ?
O7 P3 O8 114.25(17) . . ?
O7 P3 C16 112.0(2) . . ?
O7 P3 O9 110.49(19) . . ?
O8 P3 C16 105.83(18) . . ?
O8 P3 O9 106.95(18) . . ?
O9 P3 C16 106.8(2) . . ?
O10 P4 O12 109.07(16) . . ?
O10 P4 C22 107.63(17) . . ?
O11 P4 O10 112.65(15) . . ?
O11 P4 O12 108.35(16) . . ?
O11 P4 C22 109.51(16) . . ?
O12 P4 C22 109.61(17) . . ?
P1 O2 Zr1 162.94(19) . 2_655 ?
P1 O3 Zr1 143.22(16) . 4_475 ?
P3 O8 Zr1 151.01(19) . . ?
P4 O10 Zr1 167.55(19) . 2_656 ?
P4 O11 Zr1 142.74(16) . 4_576 ?
C2 C1 Si1 124.9(3) . . ?
C2 C1 C6 117.6(4) . . ?
C6 C1 Si1 117.4(3) . . ?
C1 C2 C3 121.5(4) . . ?
C4 C3 C2 119.9(4) . . ?
C3 C4 P1 122.7(3) . . ?
C3 C4 C5 119.7(4) . . ?
C5 C4 P1 117.5(3) . . ?
C6 C5 C4 119.2(4) . . ?
C5 C6 C1 121.9(4) . . ?
C8 C7 Si1 122.8(3) . . ?
C8 C7 C12 117.4(4) . . ?
C12 C7 Si1 119.7(3) . . ?
C7 C8 C9 121.5(4) . . ?
C10 C9 C8 120.8(4) . . ?
C9 C10 P2 120.6(3) . . ?
C9 C10 C11 117.8(4) . . ?
C11 C10 P2 121.6(3) . . ?
C12 C11 C10 121.1(4) . . ?
C11 C12 C7 121.2(4) . . ?
C14 C13 Si1 121.6(3) . . ?
C14 C13 C18 117.0(4) . . ?
C18 C13 Si1 121.3(3) . . ?
C15 C14 C13 121.4(4) . . ?
C14 C15 C16 119.6(4) . . ?
C15 C16 P3 118.4(3) . . ?
C17 C16 P3 121.6(3) . . ?
C17 C16 C15 120.1(4) . . ?
C16 C17 C18 120.5(4) . . ?
C17 C18 C13 121.4(4) . . ?
C20 C19 Si1 122.9(3) . . ?
C24 C19 Si1 119.7(3) . . ?
C24 C19 C20 117.2(4) . . ?
C21 C20 C19 121.3(4) . . ?
C22 C21 C20 119.5(4) . . ?
C21 C22 P4 120.0(3) . . ?
C23 C22 P4 119.7(3) . . ?
C23 C22 C21 120.2(4) . . ?
C22 C23 C24 119.9(4) . . ?
C23 C24 C19 121.9(4) . . ?
P2 O5 Zr1 154.38(19) . 1_455 ?

_olex2_submission_special_instructions 'No special instructions were received'
