# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_x_sq
_database_code_depnum_ccdc_archive 'CCDC 1450479'
_audit_update_record             
;
2016-03-29 deposited with the CCDC.
2016-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H68 N14 O16 Zn2'
_chemical_formula_weight         1251.93

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'
N N 0.0061 0.0033 '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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      cubic
_space_group_IT_number           204
_space_group_name_H-M_alt        'I m -3'
_space_group_name_Hall           '-I 2 2 3'

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

_cell_length_a                   28.6573(3)
_cell_length_b                   28.6573(3)
_cell_length_c                   28.6573(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     23534.5(7)
_cell_formula_units_Z            12
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    28386
_cell_measurement_theta_min      2.6594
_cell_measurement_theta_max      27.4932

_exptl_crystal_description       Prism
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.060
_exptl_crystal_F_000             7848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5000
_exptl_crystal_size_mid          0.4000
_exptl_crystal_size_min          0.4000
_exptl_absorpt_coefficient_mu    0.670
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8149
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Saturn724+
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            93484
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.462
_diffrn_reflns_theta_max         27.473
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4768
_reflns_number_gt                4670
_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.
 
 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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1261P)²+11.1189P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4768
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.2349
_refine_ls_wR_factor_gt          0.2318
_refine_ls_goodness_of_fit_ref   1.302
_refine_ls_restrained_S_all      1.302
_refine_ls_shift/su_max          0.093
_refine_ls_shift/su_mean         0.009

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 0.38295(2) 0.5000 0.0000 0.0553(2) Uani 1 4 d S T P . .
Zn2 Zn 0.28031(2) 0.5000 0.0000 0.0620(2) Uani 1 4 d S T P . .
O1 O 0.2094(2) 0.5000 0.0000 0.137(3) Uani 1 4 d S T P . .
H1 H 0.2021 0.5000 0.0263 0.205 Uiso 1 2 d S U P . .
O2 O 0.37100(9) 0.45025(10) 0.04929(9) 0.0917(8) Uani 1 1 d . . . . .
O3 O 0.29342(9) 0.45077(9) 0.05052(7) 0.0781(6) Uani 1 1 d . . . . .
N1 N 0.45479(15) 0.5000 0.0000 0.0593(10) Uani 1 4 d S T P . .
N2 N 0.33913(10) 0.30516(10) 0.21268(10) 0.0797(8) Uani 1 1 d . . . . .
H2A H 0.3641 0.2885 0.2117 0.096 Uiso 1 1 calc R U . . .
N3 N 0.27396(9) 0.32266(9) 0.25735(9) 0.0738(7) Uani 1 1 d . . . . .
C1 C 0.4729(2) 0.4831(2) 0.04202(18) 0.0698(15) Uani 0.5 1 d . . P . .
H1A H 0.4618 0.4519 0.0476 0.084 Uiso 0.5 1 d R U P . .
H1B H 0.4618 0.4999 0.0670 0.084 Uiso 1 2 d R U P . .
C2 C 0.4737(3) 0.5546(3) 0.0000 0.073(2) Uani 0.5 2 d S T P . .
H2B H 0.4623 0.5705 0.0272 0.087 Uiso 0.25 1 d R U P . .
H2C H 0.4623 0.5705 -0.0272 0.087 Uiso 0.25 1 d R U P . .
C3 C 0.33212(11) 0.43709(11) 0.06463(9) 0.0658(7) Uani 1 1 d . . . . .
C4 C 0.33284(10) 0.40237(11) 0.10324(9) 0.0647(7) Uani 1 1 d . . . . .
C5 C 0.37323(13) 0.37953(16) 0.11525(13) 0.0953(12) Uani 1 1 d . . . . .
H5A H 0.4003 0.3854 0.0984 0.114 Uiso 1 1 calc R U . . .
C6 C 0.37469(13) 0.34805(17) 0.15181(15) 0.0991(13) Uani 1 1 d . . . . .
H6A H 0.4026 0.3335 0.1595 0.119 Uiso 1 1 calc R U . . .
C7 C 0.33488(11) 0.33824(11) 0.17688(11) 0.0705(8) Uani 1 1 d . . . . .
C8 C 0.29349(11) 0.36028(12) 0.16460(11) 0.0758(8) Uani 1 1 d . . . . .
H8A H 0.2663 0.3542 0.1812 0.091 Uiso 1 1 calc R U . . .
C9 C 0.29287(11) 0.39123(12) 0.12782(12) 0.0746(8) Uani 1 1 d . . . . .
H9A H 0.2648 0.4050 0.1193 0.090 Uiso 1 1 calc R U . . .
C10 C 0.30962(11) 0.29529(10) 0.24894(11) 0.0690(7) 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 O2 2.036(2) 26 ?
Zn1 O2 2.036(2) 27_565 ?
Zn1 O2 2.036(2) 4_565 ?
Zn1 O2 2.036(2) . ?
Zn1 N1 2.059(4) . ?
Zn1 Zn2 2.9415(9) . ?
Zn2 O1 2.033(7) . ?
Zn2 O3 2.056(2) 27_565 ?
Zn2 O3 2.056(2) 26 ?
Zn2 O3 2.056(2) 4_565 ?
Zn2 O3 2.056(2) . ?
O2 C3 1.256(4) . ?
O3 C3 1.244(4) . ?
N1 C1 1.398(5) . ?
N1 C1 1.398(5) 27_565 ?
N1 C1 1.398(5) 26 ?
N1 C1 1.398(5) 4_565 ?
N1 C2 1.657(8) 27_565 ?
N1 C2 1.657(8) . ?
N2 C10 1.369(3) . ?
N2 C7 1.402(4) . ?
N3 C10 1.311(3) . ?
N3 C10 1.355(3) 5 ?
C1 C1 0.971(13) 27_565 ?
C1 C1 1.555(12) 28_655 ?
C1 C2 1.618(8) 27_565 ?
C1 C1 1.833(12) 2_665 ?
C2 C2 1.505(18) 3_655 ?
C2 C1 1.618(8) 4_565 ?
C2 C1 1.618(8) 27_565 ?
C3 C4 1.488(4) . ?
C4 C5 1.374(5) . ?
C4 C9 1.382(4) . ?
C5 C6 1.383(5) . ?
C6 C7 1.377(4) . ?
C7 C8 1.389(4) . ?
C8 C9 1.378(4) . ?
C10 N3 1.355(3) 9 ?

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 Zn1 O2 160.62(15) 26 27_565 ?
O2 Zn1 O2 88.89(18) 26 4_565 ?
O2 Zn1 O2 87.86(18) 27_565 4_565 ?
O2 Zn1 O2 87.86(18) 26 . ?
O2 Zn1 O2 88.89(18) 27_565 . ?
O2 Zn1 O2 160.62(15) 4_565 . ?
O2 Zn1 N1 99.69(8) 26 . ?
O2 Zn1 N1 99.69(8) 27_565 . ?
O2 Zn1 N1 99.69(8) 4_565 . ?
O2 Zn1 N1 99.69(8) . . ?
O2 Zn1 Zn2 80.31(8) 26 . ?
O2 Zn1 Zn2 80.31(8) 27_565 . ?
O2 Zn1 Zn2 80.31(8) 4_565 . ?
O2 Zn1 Zn2 80.31(8) . . ?
N1 Zn1 Zn2 180.0 . . ?
O1 Zn2 O3 100.53(7) . 27_565 ?
O1 Zn2 O3 100.53(7) . 26 ?
O3 Zn2 O3 158.94(14) 27_565 26 ?
O1 Zn2 O3 100.53(7) . 4_565 ?
O3 Zn2 O3 89.52(14) 27_565 4_565 ?
O3 Zn2 O3 86.65(14) 26 4_565 ?
O1 Zn2 O3 100.53(7) . . ?
O3 Zn2 O3 86.65(14) 27_565 . ?
O3 Zn2 O3 89.52(14) 26 . ?
O3 Zn2 O3 158.94(14) 4_565 . ?
O1 Zn2 Zn1 180.0 . . ?
O3 Zn2 Zn1 79.47(7) 27_565 . ?
O3 Zn2 Zn1 79.47(7) 26 . ?
O3 Zn2 Zn1 79.47(7) 4_565 . ?
O3 Zn2 Zn1 79.47(7) . . ?
C3 O2 Zn1 127.1(2) . . ?
C3 O3 Zn2 127.5(2) . . ?
C1 N1 C1 40.7(5) . 27_565 ?
C1 N1 C1 119.0(6) . 26 ?
C1 N1 C1 136.5(6) 27_565 26 ?
C1 N1 C1 136.5(6) . 4_565 ?
C1 N1 C1 119.0(6) 27_565 4_565 ?
C1 N1 C1 40.7(5) 26 4_565 ?
C1 N1 C2 63.3(3) . 27_565 ?
C1 N1 C2 101.9(3) 27_565 27_565 ?
C1 N1 C2 63.3(3) 26 27_565 ?
C1 N1 C2 101.9(3) 4_565 27_565 ?
C1 N1 C2 101.9(3) . . ?
C1 N1 C2 63.3(3) 27_565 . ?
C1 N1 C2 101.9(3) 26 . ?
C1 N1 C2 63.3(3) 4_565 . ?
C2 N1 C2 141.7(7) 27_565 . ?
C1 N1 Zn1 111.7(3) . . ?
C1 N1 Zn1 111.7(3) 27_565 . ?
C1 N1 Zn1 111.7(3) 26 . ?
C1 N1 Zn1 111.7(3) 4_565 . ?
C2 N1 Zn1 109.1(3) 27_565 . ?
C2 N1 Zn1 109.1(3) . . ?
C10 N2 C7 129.9(3) . . ?
C10 N3 C10 113.3(3) . 5 ?
C1 C1 N1 69.7(3) 27_565 . ?
C1 C1 C1 90.002(2) 27_565 28_655 ?
N1 C1 C1 111.8(3) . 28_655 ?
C1 C1 C2 131.9(3) 27_565 27_565 ?
N1 C1 C2 66.2(3) . 27_565 ?
C1 C1 C2 89.1(4) 28_655 27_565 ?
C1 C1 C1 58.0(4) 27_565 2_665 ?
N1 C1 C1 97.5(4) . 2_665 ?
C1 C1 C1 32.0(4) 28_655 2_665 ?
C2 C1 C1 109.9(5) 27_565 2_665 ?
C2 C2 C1 90.9(4) 3_655 4_565 ?
C2 C2 C1 90.9(4) 3_655 27_565 ?
C1 C2 C1 96.2(6) 4_565 27_565 ?
C2 C2 N1 109.1(3) 3_655 . ?
C1 C2 N1 50.5(3) 4_565 . ?
C1 C2 N1 50.5(3) 27_565 . ?
O3 C3 O2 125.6(3) . . ?
O3 C3 C4 117.7(3) . . ?
O2 C3 C4 116.7(3) . . ?
C5 C4 C9 117.4(3) . . ?
C5 C4 C3 121.1(3) . . ?
C9 C4 C3 121.5(3) . . ?
C4 C5 C6 121.7(3) . . ?
C5 C6 C7 120.2(3) . . ?
C8 C7 C6 118.8(3) . . ?
C8 C7 N2 124.5(3) . . ?
C6 C7 N2 116.6(3) . . ?
C7 C8 C9 119.8(3) . . ?
C4 C9 C8 121.9(3) . . ?
N3 C10 N3 126.7(3) . 9 ?
N3 C10 N2 119.8(3) . . ?
N3 C10 N2 113.4(2) 9 . ?

_refine_diff_density_max         1.677
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.076

_shelxl_version_number           2014-3

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.051 -0.057 -0.054 14876 2303 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?
