# Electronic Supplementary Material (ESI) for Polymer 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_Compound6
_database_code_depnum_ccdc_archive 'CCDC 1479398'
_audit_update_record             
;
2016-05-11 deposited with the CCDC.
2016-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H40 Cl2 N4 O9 Zn2'
_chemical_formula_weight         742.25

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

_cell_length_a                   20.1218(10)
_cell_length_b                   15.6745(7)
_cell_length_c                   21.2107(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6689.8(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14122
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      23.23

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_F_000             3072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    1.645
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.614
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            84165
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.1215
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.171
_diffrn_reflns_theta_max         23.320
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.796
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.796
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.796
_reflns_number_total             4829
_reflns_number_gt                3708
_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       'Bruker ApexII'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0540P)²+8.8423P] 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         4829
_refine_ls_number_parameters     390
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1098
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.119
_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
Zn1 Zn 0.09370(2) 0.66597(3) 0.32800(2) 0.01847(16) Uani 1 1 d . . . . .
Zn2 Zn 0.17574(3) 0.53111(3) 0.24046(2) 0.02266(16) Uani 1 1 d . . . . .
Cl1 Cl 0.14990(10) 0.90353(14) 0.45986(9) 0.0839(6) Uani 1 1 d . . . . .
Cl2 Cl 0.28860(16) 0.8549(2) 0.46927(17) 0.1706(16) Uani 1 1 d . . . . .
C1 C 0.0972(3) 0.6030(4) 0.4920(3) 0.0494(15) Uani 1 1 d . . . . .
H1A H 0.0800 0.5539 0.4704 0.074 Uiso 1 1 d R U . . .
H1B H 0.0944 0.5941 0.5367 0.074 Uiso 1 1 d R U . . .
H1C H 0.1428 0.6115 0.4803 0.074 Uiso 1 1 d R U . . .
C1A C 0.0799(2) 0.4659(3) 0.3224(2) 0.0292(12) Uani 1 1 d . . . . .
C1B C 0.2364(2) 0.6136(3) 0.3510(2) 0.0265(11) Uani 1 1 d . . . . .
C1C C 0.1050(2) 0.6786(3) 0.1806(2) 0.0208(10) Uani 1 1 d . . . . .
C1D C 0.2036(3) 0.4757(3) 0.1259(2) 0.0299(12) Uani 1 1 d . . . . .
C1G C 0.0109(2) 1.0038(3) 0.3263(3) 0.0371(13) Uani 1 1 d . . . . .
H1G1 H -0.0334 0.9867 0.3152 0.056 Uiso 1 1 d R U . . .
H1G2 H 0.0227 1.0541 0.3030 0.056 Uiso 1 1 d R U . . .
H1G3 H 0.0129 1.0158 0.3706 0.056 Uiso 1 1 d R U . . .
C2 C 0.0573(2) 0.6799(3) 0.4743(2) 0.0279(11) Uani 1 1 d . . . . .
C2A C 0.0404(3) 0.3959(3) 0.3527(3) 0.0610(19) Uani 1 1 d . . . . .
H2A1 H 0.0383 0.4051 0.3974 0.091 Uiso 1 1 d R U . . .
H2A2 H 0.0610 0.3419 0.3444 0.091 Uiso 1 1 d R U . . .
H2A3 H -0.0038 0.3960 0.3356 0.091 Uiso 1 1 d R U . . .
C2B C 0.2974(2) 0.6244(4) 0.3915(3) 0.0419(14) Uani 1 1 d . . . . .
H2B1 H 0.3240 0.6702 0.3753 0.063 Uiso 1 1 d R U . . .
H2B2 H 0.3228 0.5725 0.3911 0.063 Uiso 1 1 d R U . . .
H2B3 H 0.2843 0.6372 0.4340 0.063 Uiso 1 1 d R U . . .
C2C C 0.1521(2) 0.6821(3) 0.1259(2) 0.0331(12) Uani 1 1 d . . . . .
H2C1 H 0.1364 0.6451 0.0930 0.050 Uiso 1 1 d R U . . .
H2C2 H 0.1953 0.6637 0.1394 0.050 Uiso 1 1 d R U . . .
H2C3 H 0.1547 0.7394 0.1103 0.050 Uiso 1 1 d R U . . .
C2D C 0.2439(3) 0.4444(3) 0.0714(3) 0.0464(15) Uani 1 1 d . . . . .
H2D1 H 0.2148 0.4282 0.0377 0.070 Uiso 1 1 d R U . . .
H2D2 H 0.2699 0.3961 0.0842 0.070 Uiso 1 1 d R U . . .
H2D3 H 0.2729 0.4892 0.0574 0.070 Uiso 1 1 d R U . . .
C3 C 0.0240(2) 0.7365(3) 0.5133(2) 0.0321(12) Uani 1 1 d . . . . .
H3 H 0.0220 0.7345 0.5571 0.038 Uiso 1 1 calc R U . . .
C4 C -0.0055(2) 0.7960(3) 0.4751(2) 0.0250(11) Uani 1 1 d . . . . .
C5 C -0.0437(3) 0.8744(3) 0.4921(2) 0.0413(13) Uani 1 1 d . . . . .
H5A H -0.0149 0.9231 0.4898 0.062 Uiso 1 1 d R U . . .
H5B H -0.0609 0.8690 0.5341 0.062 Uiso 1 1 d R U . . .
H5C H -0.0798 0.8814 0.4630 0.062 Uiso 1 1 d R U . . .
C6 C 0.2084(2) 0.8222(3) 0.2562(3) 0.0352(12) Uani 1 1 d . . . . .
H6A H 0.2105 0.7613 0.2604 0.053 Uiso 1 1 d R U . . .
H6B H 0.2442 0.8477 0.2794 0.053 Uiso 1 1 d R U . . .
H6C H 0.2121 0.8375 0.2126 0.053 Uiso 1 1 d R U . . .
C7 C 0.1435(2) 0.8535(3) 0.2819(2) 0.0216(10) Uani 1 1 d . . . . .
C8 C 0.1193(2) 0.9364(3) 0.2826(2) 0.0278(11) Uani 1 1 d . . . . .
H8 H 0.1406 0.9846 0.2670 0.033 Uiso 1 1 calc R U . . .
C9 C 0.0582(2) 0.9338(3) 0.3107(2) 0.0227(10) Uani 1 1 d . . . . .
C11 C -0.0101(2) 0.8113(2) 0.35611(19) 0.0164(9) Uani 1 1 d . . . . .
H11 H -0.0412 0.8574 0.3663 0.020 Uiso 1 1 calc R U . . .
C12 C -0.0467(2) 0.7506(3) 0.3107(2) 0.0189(10) Uani 1 1 d . . . . .
H12 H -0.0609 0.7856 0.2749 0.023 Uiso 1 1 calc R U . . .
C13 C -0.1100(2) 0.7046(3) 0.3351(2) 0.0246(11) Uani 1 1 d . . . . .
C14 C -0.1564(2) 0.7682(3) 0.3668(3) 0.0369(13) Uani 1 1 d . . . . .
H14A H -0.1983 0.7412 0.3752 0.055 Uiso 1 1 d R U . . .
H14B H -0.1631 0.8163 0.3395 0.055 Uiso 1 1 d R U . . .
H14C H -0.1370 0.7872 0.4058 0.055 Uiso 1 1 d R U . . .
C15 C -0.0950(2) 0.6310(3) 0.3801(3) 0.0387(13) Uani 1 1 d . . . . .
H15A H -0.0780 0.6534 0.4191 0.058 Uiso 1 1 d R U . . .
H15B H -0.0625 0.5940 0.3615 0.058 Uiso 1 1 d R U . . .
H15C H -0.1349 0.5995 0.3882 0.058 Uiso 1 1 d R U . . .
C16 C -0.1453(2) 0.6695(3) 0.2766(3) 0.0367(13) Uani 1 1 d . . . . .
H16A H -0.1847 0.6395 0.2894 0.055 Uiso 1 1 d R U . . .
H16B H -0.1162 0.6312 0.2546 0.055 Uiso 1 1 d R U . . .
H16C H -0.1573 0.7159 0.2494 0.055 Uiso 1 1 d R U . . .
C17 C 0.2199(5) 0.8623(6) 0.4222(5) 0.115(4) Uani 1 1 d . . . . .
H17A H 0.2093 0.8060 0.4062 0.139 Uiso 1 1 calc R U . . .
H17B H 0.2304 0.8983 0.3863 0.139 Uiso 1 1 calc R U . . .
N1 N 0.04886(17) 0.7020(2) 0.41427(17) 0.0227(9) Uani 1 1 d . . . . .
N2 N 0.00973(17) 0.7731(2) 0.41541(16) 0.0189(8) Uani 1 1 d . . . . .
N3 N 0.10006(16) 0.8007(2) 0.30846(17) 0.0190(8) Uani 1 1 d . . . . .
N4 N 0.04693(16) 0.8506(2) 0.32551(16) 0.0171(8) Uani 1 1 d . . . . .
O1 O -0.00224(13) 0.68752(17) 0.28531(14) 0.0195(7) Uani 1 1 d . . . . .
O1A O 0.11724(17) 0.4448(2) 0.27652(16) 0.0364(9) Uani 1 1 d . . . . .
O1B O 0.23836(16) 0.5560(2) 0.30949(15) 0.0329(8) Uani 1 1 d . . . . .
O1C O 0.12298(14) 0.63770(18) 0.23099(13) 0.0199(7) Uani 1 1 d . . . . .
O1D O 0.23609(15) 0.4993(2) 0.17381(16) 0.0322(8) Uani 1 1 d D . . . .
H1D H 0.2767 0.4816 0.1789 0.039 Uiso 1 1 d DR U . . .
O2A O 0.07368(16) 0.53926(19) 0.34309(15) 0.0297(8) Uani 1 1 d . . . . .
O2B O 0.18870(14) 0.66307(19) 0.36124(15) 0.0270(7) Uani 1 1 d . . . . .
O2C O 0.05096(16) 0.7158(2) 0.17686(14) 0.0312(8) Uani 1 1 d . . . . .
O2D O 0.14205(18) 0.4774(2) 0.12409(18) 0.0429(9) 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 O2B 2.038(3) . ?
Zn1 O2A 2.052(3) . ?
Zn1 N1 2.117(4) . ?
Zn1 N3 2.156(3) . ?
Zn1 O1 2.159(3) . ?
Zn1 O1C 2.186(3) . ?
Zn2 O1D 1.929(3) . ?
Zn2 O1A 1.950(3) . ?
Zn2 O1B 1.971(3) . ?
Zn2 O1C 1.990(3) . ?
Cl1 C17 1.744(9) . ?
Cl2 C17 1.709(8) . ?
C1 C2 1.497(7) . ?
C1A O2A 1.236(5) . ?
C1A O1A 1.274(6) . ?
C1A C2A 1.500(7) . ?
C1B O2B 1.252(5) . ?
C1B O1B 1.262(6) . ?
C1B C2B 1.508(7) . ?
C1C O2C 1.238(5) . ?
C1C O1C 1.297(5) . ?
C1C C2C 1.498(6) . ?
C1D O2D 1.240(6) . ?
C1D O1D 1.263(6) . ?
C1D C2D 1.494(7) . ?
C1G C9 1.490(6) . ?
C2 N1 1.329(6) . ?
C2 C3 1.387(6) . ?
C3 C4 1.370(7) . ?
C4 N2 1.351(6) . ?
C4 C5 1.492(6) . ?
C6 C7 1.497(6) . ?
C7 N3 1.329(5) . ?
C7 C8 1.388(6) . ?
C8 C9 1.367(6) . ?
C9 N4 1.359(5) . ?
C11 N2 1.449(5) . ?
C11 N4 1.456(5) . ?
C11 C12 1.541(6) . ?
C12 O1 1.437(5) . ?
C12 C13 1.552(6) . ?
C13 C14 1.523(6) . ?
C13 C15 1.528(7) . ?
C13 C16 1.532(6) . ?
N1 N2 1.365(5) . ?
N3 N4 1.373(5) . ?

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
O2B Zn1 O2A 96.23(13) . . ?
O2B Zn1 N1 96.12(13) . . ?
O2A Zn1 N1 92.27(13) . . ?
O2B Zn1 N3 91.88(13) . . ?
O2A Zn1 N3 171.84(13) . . ?
N1 Zn1 N3 86.00(13) . . ?
O2B Zn1 O1 170.88(12) . . ?
O2A Zn1 O1 92.36(12) . . ?
N1 Zn1 O1 86.55(12) . . ?
N3 Zn1 O1 79.58(11) . . ?
O2B Zn1 O1C 93.92(12) . . ?
O2A Zn1 O1C 90.20(12) . . ?
N1 Zn1 O1C 169.33(12) . . ?
N3 Zn1 O1C 90.10(12) . . ?
O1 Zn1 O1C 82.98(11) . . ?
O1D Zn2 O1A 119.23(14) . . ?
O1D Zn2 O1B 101.14(14) . . ?
O1A Zn2 O1B 103.43(15) . . ?
O1D Zn2 O1C 118.60(13) . . ?
O1A Zn2 O1C 107.47(13) . . ?
O1B Zn2 O1C 104.46(12) . . ?
O2A C1A O1A 124.9(4) . . ?
O2A C1A C2A 118.4(4) . . ?
O1A C1A C2A 116.7(4) . . ?
O2B C1B O1B 126.0(4) . . ?
O2B C1B C2B 117.1(4) . . ?
O1B C1B C2B 116.8(4) . . ?
O2C C1C O1C 122.0(4) . . ?
O2C C1C C2C 119.2(4) . . ?
O1C C1C C2C 118.7(4) . . ?
O2D C1D O1D 122.4(5) . . ?
O2D C1D C2D 121.6(5) . . ?
O1D C1D C2D 116.0(5) . . ?
N1 C2 C3 110.1(4) . . ?
N1 C2 C1 121.3(4) . . ?
C3 C2 C1 128.6(4) . . ?
C4 C3 C2 106.9(4) . . ?
N2 C4 C3 106.0(4) . . ?
N2 C4 C5 124.1(4) . . ?
C3 C4 C5 129.8(4) . . ?
N3 C7 C8 110.3(4) . . ?
N3 C7 C6 121.6(4) . . ?
C8 C7 C6 128.1(4) . . ?
C9 C8 C7 107.0(4) . . ?
N4 C9 C8 106.2(4) . . ?
N4 C9 C1G 123.3(4) . . ?
C8 C9 C1G 130.5(4) . . ?
N2 C11 N4 110.2(3) . . ?
N2 C11 C12 114.7(3) . . ?
N4 C11 C12 111.0(3) . . ?
O1 C12 C11 111.3(3) . . ?
O1 C12 C13 108.4(3) . . ?
C11 C12 C13 118.0(4) . . ?
C14 C13 C15 109.8(4) . . ?
C14 C13 C16 107.9(4) . . ?
C15 C13 C16 109.1(4) . . ?
C14 C13 C12 110.3(4) . . ?
C15 C13 C12 113.4(4) . . ?
C16 C13 C12 106.2(4) . . ?
Cl2 C17 Cl1 114.2(5) . . ?
C2 N1 N2 105.6(3) . . ?
C2 N1 Zn1 134.7(3) . . ?
N2 N1 Zn1 118.6(3) . . ?
C4 N2 N1 111.4(3) . . ?
C4 N2 C11 129.9(4) . . ?
N1 N2 C11 118.8(3) . . ?
C7 N3 N4 105.6(3) . . ?
C7 N3 Zn1 136.9(3) . . ?
N4 N3 Zn1 117.5(2) . . ?
C9 N4 N3 110.8(3) . . ?
C9 N4 C11 129.8(3) . . ?
N3 N4 C11 119.4(3) . . ?
C12 O1 Zn1 120.4(2) . . ?
C1A O1A Zn2 118.4(3) . . ?
C1B O1B Zn2 129.8(3) . . ?
C1C O1C Zn2 130.3(3) . . ?
C1C O1C Zn1 126.9(3) . . ?
Zn2 O1C Zn1 102.65(12) . . ?
C1D O1D Zn2 109.8(3) . . ?
C1A O2A Zn1 145.6(3) . . ?
C1B O2B Zn1 132.2(3) . . ?

_refine_diff_density_max         0.604
_refine_diff_density_min         -0.750
_refine_diff_density_rms         0.090

_shelxl_version_number           2014-3

