# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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 have may 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_s1373
_database_code_depnum_ccdc_archive 'CCDC 1023946'
_audit_update_record             
;
2014-09-23 deposited with the CCDC.
2014-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 N O39 Zr6'
_chemical_formula_weight         1377.58

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'C m c m'
_symmetry_space_group_name_H-M_alt 'P m n b'
_space_group_name_Hall           '-C 2c 2'

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

_cell_length_a                   10.04970(10)
_cell_length_b                   19.9849(3)
_cell_length_c                   19.7712(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3970.89(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    24693
_cell_measurement_theta_min      4.4070
_cell_measurement_theta_max      75.5360

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2644
_exptl_absorpt_coefficient_mu    13.618
_exptl_absorpt_correction_T_min  0.52949
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5861
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            35477
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.42
_diffrn_reflns_theta_max         75.89
_reflns_number_total             2259
_reflns_number_gt                2097
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1106P)²+53.6045P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2259
_refine_ls_number_parameters     145
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1729
_refine_ls_wR_factor_gt          0.1687
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C30A C 0.0000 0.958(2) 0.9092(11) 0.063(7) Uiso 0.65(5) 2 d SP . 1
H30A H 0.0000 0.9121 0.9010 0.075 Uiso 0.65(5) 2 calc SPR . 1
O30A O 0.1090(9) 0.9938(10) 0.9157(5) 0.041(3) Uiso 0.65(5) 1 d P . 1
C30B C 0.0000 0.985(2) 0.9094(13) 0.033(8) Uiso 0.35(5) 2 d SP . 2
H30B H 0.0000 1.0159 0.8744 0.040 Uiso 0.35(5) 2 calc SPR . 2
O30B O 0.1096(14) 0.9712(13) 0.9248(8) 0.029(6) Uiso 0.35(5) 1 d P . 2
N50 N 0.933(4) 0.809(2) 0.7500 0.144(17) Uiso 0.50 2 d SPD A 2
C52 C 1.0000 0.743(2) 0.7500 0.22(3) Uiso 1 4 d SD A 2
C51 C 1.020(8) 0.869(4) 0.7500 0.26(4) Uiso 0.50 2 d SPD A 2
C50 C 0.805(4) 0.8148(18) 0.7500 0.118(16) Uiso 0.50 2 d SPD A 2
O50 O 0.750(4) 0.758(2) 0.7500 0.20(2) Uiso 0.50 2 d SPD A 2
O20 O 0.3683(6) 1.1623(3) 0.8962(3) 0.0501(13) Uani 1 1 d . . 2
C20 C 0.2848(10) 1.1347(5) 0.8577(5) 0.060(2) Uani 1 1 d . . 2
H20 H 0.2404 1.1627 0.8276 0.071 Uiso 1 1 calc R . 2
O40 O 0.3382(5) 0.9566(3) 0.8056(2) 0.0453(12) Uani 1 1 d . . 2
O21 O 0.2548(6) 1.0742(3) 0.8551(4) 0.0623(17) Uani 1 1 d . . 2
C40 C 0.314(2) 0.9797(9) 0.7500 0.081(5) Uani 1 2 d S . 2
H40 H 0.2710 1.0209 0.7500 0.097 Uiso 1 2 calc SR . 2
O2B O 0.5000 0.9122(7) 0.9105(6) 0.030(3) Uiso 0.50 2 d SP . 2
O3A O 0.5000 1.0348(6) 0.9125(7) 0.026(2) Uiso 0.50 2 d SP . 2
O3B O 0.5000 1.0448(6) 0.8851(7) 0.028(3) Uiso 0.50 2 d SP . 2
O2A O 0.5000 0.9341(6) 0.9375(6) 0.029(2) Uiso 0.50 2 d SP . 2
O1B O 0.2964(12) 1.0659(5) 0.9836(5) 0.038(2) Uiso 0.50 1 d P . 2
Zr1 Zr 0.32374(5) 0.98136(3) 0.91244(3) 0.0301(2) Uani 1 1 d . . 2
Zr2 Zr 0.5000 1.11995(4) 0.97395(4) 0.0338(3) Uani 1 2 d S . 2
O1A O 0.3507(11) 1.0519(5) 0.9901(5) 0.0334(19) Uiso 0.50 1 d P . 2
O11 O 0.2511(6) 0.8743(3) 0.9000(3) 0.0535(14) Uani 1 1 d . . 2
O10 O 0.3681(6) 1.1900(3) 1.0277(3) 0.0468(12) Uani 1 1 d . . 2
C10 C 0.2810(10) 0.8202(4) 0.9269(5) 0.055(2) Uani 1 1 d . . 2
H10 H 0.2342 0.7828 0.9122 0.066 Uiso 1 1 calc R . 2
O1W O 0.0000 0.6154(6) 0.7500 0.052(3) Uiso 1 4 d S B 2
O4W O 0.0000 0.098(2) 0.7500 0.188(14) Uiso 1 4 d S C 2
O3W O 0.5000 0.3453(18) 0.0384(17) 0.234(13) Uiso 1 2 d S D 2
O2W O 0.5000 0.7985(15) 0.7065(12) 0.192(10) Uiso 1 2 d S . .


_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
C30A O30A 1.32(3) . ?
C30A O30A 1.32(3) 11 ?
C30B O30B 1.18(2) 11 ?
C30B O30B 1.18(2) . ?
O30B Zr1 2.175(14) . ?
N50 C50 1.29(2) . ?
N50 C52 1.486(16) . ?
N50 C51 1.495(16) . ?
C50 O50 1.266(19) . ?
O20 C20 1.260(11) . ?
O20 Zr2 2.198(5) . ?
C20 O21 1.248(11) . ?
O40 C40 1.216(10) . ?
O40 Zr1 2.175(5) . ?
O21 Zr1 2.281(6) . ?
C40 O40 1.216(10) 10_557 ?
O2B Zr1 2.248(8) 11_655 ?
O2B Zr1 2.248(8) . ?
O2B Zr2 2.372(12) 9_677 ?
O3A Zr1 2.068(6) 11_655 ?
O3A Zr1 2.068(6) . ?
O3A Zr2 2.091(12) . ?
O3B Zr1 2.244(8) 11_655 ?
O3B Zr1 2.244(8) . ?
O3B Zr2 2.312(13) . ?
O2A Zr2 2.056(12) 9_677 ?
O2A Zr1 2.068(6) . ?
O2A Zr1 2.068(6) 11_655 ?
O1B Zr1 2.216(10) . ?
O1B Zr1 2.278(10) 3_577 ?
O1B Zr2 2.322(11) . ?
Zr1 O1A 2.057(9) 3_577 ?
Zr1 O1A 2.102(9) . ?
Zr1 O11 2.273(5) . ?
Zr1 O1B 2.278(10) 3_577 ?
Zr2 O1A 2.049(10) . ?
Zr2 O1A 2.049(10) 11_655 ?
Zr2 O2A 2.056(12) 9_677 ?
Zr2 O20 2.198(6) 11_655 ?
Zr2 O10 2.201(5) 11_655 ?
Zr2 O10 2.201(5) . ?
Zr2 O1B 2.322(11) 11_655 ?
Zr2 O2B 2.372(12) 9_677 ?
O1A Zr1 2.057(9) 3_577 ?
O11 C10 1.243(11) . ?
O10 C10 1.270(11) 3_577 ?
C10 O10 1.270(11) 3_577 ?

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
O30A C30A O30A 113(4) . 11 ?
O30B C30B O30B 139(5) 11 . ?
C30B O30B Zr1 151(3) . . ?
C50 N50 C52 122(2) . . ?
C50 N50 C51 121(2) . . ?
C52 N50 C51 117(4) . . ?
O50 C50 N50 110.5(17) . . ?
C20 O20 Zr2 130.9(5) . . ?
O21 C20 O20 127.5(8) . . ?
C40 O40 Zr1 141.1(9) . . ?
C20 O21 Zr1 134.0(6) . . ?
O40 C40 O40 129.3(17) 10_557 . ?
Zr1 O2B Zr1 104.0(5) 11_655 . ?
Zr1 O2B Zr2 98.6(4) 11_655 9_677 ?
Zr1 O2B Zr2 98.6(4) . 9_677 ?
Zr1 O3A Zr1 117.9(6) 11_655 . ?
Zr1 O3A Zr2 114.9(4) 11_655 . ?
Zr1 O3A Zr2 114.9(4) . . ?
Zr1 O3B Zr1 104.2(5) 11_655 . ?
Zr1 O3B Zr2 100.6(4) 11_655 . ?
Zr1 O3B Zr2 100.6(4) . . ?
Zr2 O2A Zr1 116.4(3) 9_677 . ?
Zr2 O2A Zr1 116.4(3) 9_677 11_655 ?
Zr1 O2A Zr1 117.9(6) . 11_655 ?
Zr1 O1B Zr1 104.0(4) . 3_577 ?
Zr1 O1B Zr2 101.1(4) . . ?
Zr1 O1B Zr2 99.3(4) 3_577 . ?
O1A Zr1 O2A 61.0(4) 3_577 . ?
O1A Zr1 O3A 93.1(5) 3_577 . ?
O2A Zr1 O3A 60.1(4) . . ?
O2A Zr1 O1A 91.2(5) . . ?
O3A Zr1 O1A 62.8(4) . . ?
O1A Zr1 O30B 89.7(7) 3_577 . ?
O2A Zr1 O30B 141.1(8) . . ?
O3A Zr1 O30B 153.5(7) . . ?
O1A Zr1 O30B 96.2(5) . . ?
O1A Zr1 O40 145.9(3) 3_577 . ?
O2A Zr1 O40 94.1(4) . . ?
O3A Zr1 O40 93.5(4) . . ?
O1A Zr1 O40 148.6(3) . . ?
O30B Zr1 O40 98.9(4) . . ?
O2A Zr1 O1B 107.6(5) . . ?
O3A Zr1 O1B 73.3(4) . . ?
O30B Zr1 O1B 82.9(5) . . ?
O40 Zr1 O1B 143.0(3) . . ?
O1A Zr1 O3B 107.7(5) 3_577 . ?
O2A Zr1 O3B 68.9(4) . . ?
O1A Zr1 O3B 72.3(4) . . ?
O30B Zr1 O3B 149.4(8) . . ?
O40 Zr1 O3B 80.9(4) . . ?
O1B Zr1 O3B 79.7(4) . . ?
O1A Zr1 O2B 73.3(4) 3_577 . ?
O3A Zr1 O2B 69.1(4) . . ?
O1A Zr1 O2B 108.9(4) . . ?
O30B Zr1 O2B 136.4(8) . . ?
O40 Zr1 O2B 77.9(4) . . ?
O1B Zr1 O2B 125.3(4) . . ?
O3B Zr1 O2B 73.8(4) . . ?
O1A Zr1 O11 80.7(3) 3_577 . ?
O2A Zr1 O11 82.6(4) . . ?
O3A Zr1 O11 139.5(3) . . ?
O1A Zr1 O11 138.7(3) . . ?
O30B Zr1 O11 66.9(7) . . ?
O40 Zr1 O11 72.7(2) . . ?
O1B Zr1 O11 138.2(3) . . ?
O3B Zr1 O11 139.3(3) . . ?
O2B Zr1 O11 70.9(3) . . ?
O2A Zr1 O1B 72.4(4) . 3_577 ?
O3A Zr1 O1B 108.5(5) . 3_577 ?
O30B Zr1 O1B 75.0(7) . 3_577 ?
O40 Zr1 O1B 142.2(3) . 3_577 ?
O3B Zr1 O1B 123.1(5) . 3_577 ?
O2B Zr1 O1B 81.7(4) . 3_577 ?
O11 Zr1 O1B 70.6(3) . 3_577 ?
O1A Zr1 O21 140.2(3) 3_577 . ?
O2A Zr1 O21 138.6(3) . . ?
O3A Zr1 O21 80.8(4) . . ?
O1A Zr1 O21 81.7(3) . . ?
O30B Zr1 O21 80.3(8) . . ?
O40 Zr1 O21 73.9(2) . . ?
O1B Zr1 O21 70.0(3) . . ?
O3B Zr1 O21 70.2(3) . . ?
O2B Zr1 O21 137.0(3) . . ?
O11 Zr1 O21 127.9(2) . . ?
O1B Zr1 O21 138.5(3) 3_577 . ?
O1A Zr2 O2A 61.3(3) . 9_677 ?
O1A Zr2 O2A 61.3(3) 11_655 9_677 ?
O1A Zr2 O3A 63.3(3) . . ?
O1A Zr2 O3A 63.3(3) 11_655 . ?
O2A Zr2 O3A 93.8(5) 9_677 . ?
O1A Zr2 O20 85.6(3) . . ?
O1A Zr2 O20 143.6(3) 11_655 . ?
O2A Zr2 O20 142.88(18) 9_677 . ?
O3A Zr2 O20 84.7(3) . . ?
O1A Zr2 O20 143.6(3) . 11_655 ?
O1A Zr2 O20 85.6(3) 11_655 11_655 ?
O2A Zr2 O20 142.88(18) 9_677 11_655 ?
O3A Zr2 O20 84.7(3) . 11_655 ?
O20 Zr2 O20 74.1(3) . 11_655 ?
O1A Zr2 O10 142.0(3) . 11_655 ?
O1A Zr2 O10 84.6(3) 11_655 11_655 ?
O2A Zr2 O10 85.6(3) 9_677 11_655 ?
O3A Zr2 O10 142.95(16) . 11_655 ?
O20 Zr2 O10 117.1(2) . 11_655 ?
O20 Zr2 O10 74.3(2) 11_655 11_655 ?
O1A Zr2 O10 84.6(3) . . ?
O1A Zr2 O10 142.0(3) 11_655 . ?
O2A Zr2 O10 85.6(3) 9_677 . ?
O3A Zr2 O10 142.95(16) . . ?
O20 Zr2 O10 74.3(2) . . ?
O20 Zr2 O10 117.1(2) 11_655 . ?
O10 Zr2 O10 74.0(3) 11_655 . ?
O1A Zr2 O3B 71.8(3) . . ?
O1A Zr2 O3B 71.8(3) 11_655 . ?
O2A Zr2 O3B 107.8(5) 9_677 . ?
O20 Zr2 O3B 73.7(3) . . ?
O20 Zr2 O3B 73.7(3) 11_655 . ?
O10 Zr2 O3B 141.27(18) 11_655 . ?
O10 Zr2 O3B 141.27(18) . . ?
O2A Zr2 O1B 71.7(3) 9_677 . ?
O3A Zr2 O1B 70.7(3) . . ?
O20 Zr2 O1B 72.9(3) . . ?
O20 Zr2 O1B 140.1(3) 11_655 . ?
O10 Zr2 O1B 141.9(3) 11_655 . ?
O10 Zr2 O1B 74.1(3) . . ?
O3B Zr2 O1B 76.1(3) . . ?
O2A Zr2 O1B 71.7(3) 9_677 11_655 ?
O3A Zr2 O1B 70.7(3) . 11_655 ?
O20 Zr2 O1B 140.1(3) . 11_655 ?
O20 Zr2 O1B 72.9(3) 11_655 11_655 ?
O10 Zr2 O1B 74.1(3) 11_655 11_655 ?
O10 Zr2 O1B 141.9(3) . 11_655 ?
O3B Zr2 O1B 76.1(3) . 11_655 ?
O1A Zr2 O2B 70.8(3) . 9_677 ?
O1A Zr2 O2B 70.8(3) 11_655 9_677 ?
O3A Zr2 O2B 109.8(5) . 9_677 ?
O20 Zr2 O2B 141.02(19) . 9_677 ?
O20 Zr2 O2B 141.02(19) 11_655 9_677 ?
O10 Zr2 O2B 73.0(3) 11_655 9_677 ?
O10 Zr2 O2B 73.0(3) . 9_677 ?
O3B Zr2 O2B 123.8(5) . 9_677 ?
O1B Zr2 O2B 78.2(3) . 9_677 ?
O1B Zr2 O2B 78.2(3) 11_655 9_677 ?
Zr2 O1A Zr1 117.2(5) . 3_577 ?
Zr2 O1A Zr1 115.2(4) . . ?
Zr1 O1A Zr1 116.7(4) 3_577 . ?
C10 O11 Zr1 134.1(5) . . ?
C10 O10 Zr2 130.8(5) 3_577 . ?
O11 C10 O10 127.5(7) . 3_577 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        75.89
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.313
_refine_diff_density_min         -1.214
_refine_diff_density_rms         0.240
