# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1503848'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H46 N4 O26 S2 Zn3'
_chemical_formula_sum            'C38 H46 N4 O26 S2 Zn3'
_chemical_formula_weight         1235.02

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'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   28.5122(6)
_cell_length_b                   11.1716(2)
_cell_length_c                   18.7315(3)
_cell_angle_alpha                90
_cell_angle_beta                 123.991(2)
_cell_angle_gamma                90
_cell_volume                     4946.96(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    298
_cell_measurement_reflns_used    5451
_cell_measurement_theta_min      3.1530
_cell_measurement_theta_max      71.1800

_exptl_crystal_description       sheet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_F_000             2528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    3.303
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.60945
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9527
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.739
_diffrn_reflns_theta_max         71.233
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4661
_reflns_number_gt                4101
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND. Version 3.0. Crystal Impact'
_computing_publication_material  'Windows Word 2003'
_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     
'w=1/[σ²(Fo²)+(0.0624P)²+3.7954P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4661
_refine_ls_number_parameters     360
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.088
_refine_ls_shift/su_mean         0.002

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 0.11196(2) 0.41626(3) 0.14230(2) 0.02912(11) Uani 1 1 d . . . . .
Zn2 Zn 0.000000 -0.16840(5) -0.250000 0.03610(14) Uani 1 2 d S T P . .
S1 S -0.24407(2) 0.12247(6) 0.15968(4) 0.03118(15) Uani 1 1 d . . . . .
O1 O -0.01076(8) 0.36880(16) 0.06849(11) 0.0343(4) Uani 1 1 d . . . . .
O2 O 0.05572(8) 0.30793(18) 0.05033(13) 0.0417(4) Uani 1 1 d . . . . .
O3 O -0.04941(8) -0.11555(17) -0.21197(12) 0.0380(4) Uani 1 1 d . . . . .
O4 O 0.02685(9) -0.0046(2) -0.14851(14) 0.0505(5) Uani 1 1 d . . . . .
O5 O -0.23818(9) -0.00744(17) 0.16141(15) 0.0476(5) Uani 1 1 d . . . . .
O6 O -0.22804(10) 0.1632(2) 0.24516(13) 0.0499(5) Uani 1 1 d . . . . .
O7 O -0.30327(8) 0.15682(19) 0.09616(14) 0.0481(5) Uani 1 1 d . . . . .
O8 O -0.20785(9) 0.1790(2) 0.13666(14) 0.0524(5) Uani 1 1 d . . . . .
N1 N -0.15961(8) -0.03513(18) -0.03305(13) 0.0286(4) Uani 1 1 d . . . . .
N2 N -0.11092(10) -0.4422(2) 0.28812(15) 0.0364(5) Uani 1 1 d . . . . .
C1 C 0.00703(10) 0.3010(2) 0.03560(14) 0.0286(5) Uani 1 1 d . . . . .
C2 C -0.03001(10) 0.2026(2) -0.02535(14) 0.0273(5) Uani 1 1 d . . . . .
C3 C -0.01135(10) 0.1367(2) -0.06755(15) 0.0290(5) Uani 1 1 d . . . . .
H3 H 0.023845 0.155920 -0.059206 0.035 Uiso 1 1 calc R U . . .
C4 C -0.04329(10) 0.0431(2) -0.12170(14) 0.0282(5) Uani 1 1 d . . . . .
C5 C -0.01980(11) -0.0281(2) -0.16265(15) 0.0324(5) Uani 1 1 d . . . . .
C6 C -0.09515(10) 0.0149(2) -0.13437(14) 0.0274(5) Uani 1 1 d . . . . .
H6 H -0.117548 -0.048341 -0.172121 0.033 Uiso 1 1 calc R U . . .
C7 C -0.11397(9) 0.0798(2) -0.09153(14) 0.0247(4) Uani 1 1 d . . . . .
C8 C -0.08136(10) 0.1738(2) -0.03738(14) 0.0268(5) Uani 1 1 d . . . . .
H8 H -0.094337 0.218502 -0.008493 0.032 Uiso 1 1 calc R U . . .
C9 C -0.16932(10) 0.0483(2) -0.10284(15) 0.0288(5) Uani 1 1 d . . . . .
H9A H -0.187857 0.122222 -0.101266 0.035 Uiso 1 1 calc R U . . .
H9B H -0.194837 0.009827 -0.159638 0.035 Uiso 1 1 calc R U . . .
C10 C -0.16079(13) 0.0043(2) 0.03327(18) 0.0385(6) Uani 1 1 d . . . . .
H10 H -0.168694 0.086295 0.035592 0.046 Uiso 1 1 calc R U . . .
C11 C -0.14802(13) -0.1504(2) -0.03721(18) 0.0410(6) Uani 1 1 d . . . . .
H11 H -0.147440 -0.177508 -0.084784 0.049 Uiso 1 1 calc R U . . .
C12 C -0.15082(14) -0.0713(2) 0.09809(19) 0.0425(6) Uani 1 1 d . . . . .
H12 H -0.152245 -0.041893 0.144431 0.051 Uiso 1 1 calc R U . . .
C13 C -0.13704(14) -0.2294(3) 0.0263(2) 0.0456(7) Uani 1 1 d . . . . .
H13 H -0.128319 -0.310392 0.022962 0.055 Uiso 1 1 calc R U . . .
C14 C -0.13861(12) -0.1912(2) 0.09567(18) 0.0362(6) Uani 1 1 d . . . . .
C15 C -0.12731(12) -0.2756(2) 0.16478(18) 0.0389(6) Uani 1 1 d . . . . .
C16 C -0.15493(13) -0.2645(3) 0.20643(18) 0.0407(6) Uani 1 1 d . . . . .
H16 H -0.179684 -0.199021 0.193800 0.049 Uiso 1 1 calc R U . . .
C17 C -0.08956(15) -0.3704(3) 0.1898(2) 0.0556(9) Uani 1 1 d . . . . .
H17 H -0.068558 -0.379506 0.164754 0.067 Uiso 1 1 calc R U . . .
C18 C -0.14610(13) -0.3493(2) 0.26623(18) 0.0400(6) Uani 1 1 d . . . . .
H18 H -0.165933 -0.341405 0.293215 0.048 Uiso 1 1 calc R U . . .
C19 C -0.08258(15) -0.4505(3) 0.2503(2) 0.0525(8) Uani 1 1 d . . . . .
H19 H -0.056613 -0.514556 0.266264 0.063 Uiso 1 1 calc R U . . .
O1W O 0.11740(8) 0.29600(19) 0.23211(14) 0.0436(5) Uani 1 1 d D . . . .
O2W O 0.19284(9) 0.3783(2) 0.19007(16) 0.0512(5) Uani 1 1 d D . . . .
O3W O 0.11022(8) 0.51176(19) 0.04508(13) 0.0431(4) Uani 1 1 d D . . . .
O4W O -0.05047(9) -0.2956(2) -0.33601(14) 0.0500(5) Uani 1 1 d D . . . .
O5W O -0.16153(12) -0.3114(4) -0.43081(18) 0.0933(12) Uani 1 1 d D . . . .
H1WA H 0.096(2) 0.237(4) 0.213(4) 0.140 Uiso 1 1 d D U . . .
H2WA H 0.211(2) 0.321(4) 0.221(3) 0.140 Uiso 1 1 d D U . . .
H3WA H 0.1356(19) 0.561(4) 0.062(4) 0.140 Uiso 1 1 d D U . . .
H4WA H -0.040(3) -0.304(6) -0.369(3) 0.140 Uiso 1 1 d D U . . .
H5WA H -0.181(2) -0.275(5) -0.419(4) 0.140 Uiso 1 1 d D U . . .
H1WB H 0.1497(11) 0.274(6) 0.267(3) 0.140 Uiso 1 1 d D U . . .
H2WB H 0.209(2) 0.418(5) 0.174(4) 0.140 Uiso 1 1 d D U . . .
H3WB H 0.0795(13) 0.544(5) 0.023(4) 0.140 Uiso 1 1 d D U . . .
H4WB H -0.0848(6) -0.286(6) -0.362(4) 0.140 Uiso 1 1 d D U . . .
H5WB H -0.174(2) -0.313(6) -0.4821(11) 0.140 Uiso 1 1 d D U . . .


_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 1.9785(18) . ?
Zn1 O2W 1.998(2) . ?
Zn1 N2 2.060(2) 2_565 ?
Zn1 O3W 2.087(2) . ?
Zn1 O1W 2.090(2) . ?
Zn2 O3 1.9906(18) 2_554 ?
Zn2 O3 1.9907(18) . ?
Zn2 O4W 2.023(2) . ?
Zn2 O4W 2.023(2) 2_554 ?
Zn2 O4 2.434(2) 2_554 ?
Zn2 O4 2.434(2) . ?
Zn2 C5 2.547(2) . ?
Zn2 C5 2.547(2) 2_554 ?
S1 O5 1.459(2) . ?
S1 O8 1.466(2) . ?
S1 O6 1.470(2) . ?
S1 O7 1.472(2) . ?
O1 C1 1.249(3) . ?
O2 C1 1.258(3) . ?
O3 C5 1.284(3) . ?
O4 C5 1.231(3) . ?
N1 C10 1.336(3) . ?
N1 C11 1.343(3) . ?
N1 C9 1.500(3) . ?
N2 C18 1.339(3) . ?
N2 C19 1.342(4) . ?
C1 C2 1.509(3) . ?
C2 C3 1.386(3) . ?
C2 C8 1.389(3) . ?
C3 C4 1.385(3) . ?
C4 C6 1.396(3) . ?
C4 C5 1.498(3) . ?
C6 C7 1.392(3) . ?
C7 C8 1.394(3) . ?
C7 C9 1.512(3) . ?
C10 C12 1.372(4) . ?
C11 C13 1.369(4) . ?
C12 C14 1.391(4) . ?
C13 C14 1.393(4) . ?
C14 C15 1.484(4) . ?
C15 C16 1.390(4) . ?
C15 C17 1.391(4) . ?
C16 C18 1.378(4) . ?
C17 C19 1.369(4) . ?

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 O2W 115.52(10) . . ?
O2 Zn1 N2 136.81(9) . 2_565 ?
O2W Zn1 N2 107.51(10) . 2_565 ?
O2 Zn1 O3W 86.60(8) . . ?
O2W Zn1 O3W 87.58(9) . . ?
N2 Zn1 O3W 99.09(9) 2_565 . ?
O2 Zn1 O1W 88.11(8) . . ?
O2W Zn1 O1W 87.44(8) . . ?
N2 Zn1 O1W 90.28(9) 2_565 . ?
O3W Zn1 O1W 170.36(9) . . ?
O3 Zn2 O3 145.49(11) 2_554 . ?
O3 Zn2 O4W 104.72(8) 2_554 . ?
O3 Zn2 O4W 99.36(8) . . ?
O3 Zn2 O4W 99.36(8) 2_554 2_554 ?
O3 Zn2 O4W 104.71(8) . 2_554 ?
O4W Zn2 O4W 90.75(15) . 2_554 ?
O3 Zn2 O4 58.26(7) 2_554 2_554 ?
O3 Zn2 O4 94.59(7) . 2_554 ?
O4W Zn2 O4 97.66(9) . 2_554 ?
O4W Zn2 O4 157.42(7) 2_554 2_554 ?
O3 Zn2 O4 94.59(7) 2_554 . ?
O3 Zn2 O4 58.25(7) . . ?
O4W Zn2 O4 157.41(7) . . ?
O4W Zn2 O4 97.66(9) 2_554 . ?
O4 Zn2 O4 82.46(12) 2_554 . ?
O3 Zn2 C5 120.19(8) 2_554 . ?
O3 Zn2 C5 29.78(8) . . ?
O4W Zn2 C5 129.01(8) . . ?
O4W Zn2 C5 103.60(9) 2_554 . ?
O4 Zn2 C5 87.31(8) 2_554 . ?
O4 Zn2 C5 28.49(7) . . ?
O3 Zn2 C5 29.78(8) 2_554 2_554 ?
O3 Zn2 C5 120.19(8) . 2_554 ?
O4W Zn2 C5 103.61(9) . 2_554 ?
O4W Zn2 C5 129.01(8) 2_554 2_554 ?
O4 Zn2 C5 28.50(7) 2_554 2_554 ?
O4 Zn2 C5 87.32(8) . 2_554 ?
C5 Zn2 C5 104.03(11) . 2_554 ?
O5 S1 O8 110.10(13) . . ?
O5 S1 O6 108.79(13) . . ?
O8 S1 O6 110.22(12) . . ?
O5 S1 O7 110.06(13) . . ?
O8 S1 O7 109.15(13) . . ?
O6 S1 O7 108.50(14) . . ?
C1 O2 Zn1 119.13(16) . . ?
C5 O3 Zn2 99.84(15) . . ?
C5 O4 Zn2 80.85(16) . . ?
C10 N1 C11 120.3(2) . . ?
C10 N1 C9 121.2(2) . . ?
C11 N1 C9 118.5(2) . . ?
C18 N2 C19 117.4(2) . . ?
C18 N2 Zn1 121.03(18) . 2_545 ?
C19 N2 Zn1 120.44(19) . 2_545 ?
O1 C1 O2 123.9(2) . . ?
O1 C1 C2 120.6(2) . . ?
O2 C1 C2 115.5(2) . . ?
C3 C2 C8 119.4(2) . . ?
C3 C2 C1 119.3(2) . . ?
C8 C2 C1 121.3(2) . . ?
C4 C3 C2 120.9(2) . . ?
C3 C4 C6 119.6(2) . . ?
C3 C4 C5 118.5(2) . . ?
C6 C4 C5 121.8(2) . . ?
O4 C5 O3 121.0(2) . . ?
O4 C5 C4 121.0(2) . . ?
O3 C5 C4 118.0(2) . . ?
O4 C5 Zn2 70.66(15) . . ?
O3 C5 Zn2 50.37(12) . . ?
C4 C5 Zn2 168.23(18) . . ?
C7 C6 C4 119.8(2) . . ?
C6 C7 C8 119.8(2) . . ?
C6 C7 C9 120.4(2) . . ?
C8 C7 C9 119.8(2) . . ?
C2 C8 C7 120.4(2) . . ?
N1 C9 C7 110.68(18) . . ?
N1 C10 C12 121.3(2) . . ?
N1 C11 C13 120.8(2) . . ?
C10 C12 C14 119.7(2) . . ?
C11 C13 C14 120.2(3) . . ?
C12 C14 C13 117.7(2) . . ?
C12 C14 C15 121.3(2) . . ?
C13 C14 C15 121.0(2) . . ?
C16 C15 C17 117.0(3) . . ?
C16 C15 C14 121.2(2) . . ?
C17 C15 C14 121.8(2) . . ?
C18 C16 C15 119.4(3) . . ?
C19 C17 C15 120.2(3) . . ?
N2 C18 C16 123.2(2) . . ?
N2 C19 C17 122.7(3) . . ?

_refine_diff_density_max         1.130
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1503847'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 Br0.40 N2.60 O8.80 Zn'
_chemical_formula_sum            'C19 H19 Br0.40 N2.60 O8.80 Zn'
_chemical_formula_weight         521.90

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'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   15.7072(3)
_cell_length_b                   10.7130(2)
_cell_length_c                   24.4618(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.280(2)
_cell_angle_gamma                90
_cell_volume                     4104.74(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    296
_cell_measurement_reflns_used    4345
_cell_measurement_theta_min      4.9830
_cell_measurement_theta_max      74.4500

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      1.689
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_F_000             2125
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    3.090
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.45466
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3503
_diffrn_reflns_number            7303
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.624
_diffrn_reflns_theta_max         74.491
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4066
_reflns_number_gt                3724
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND. Version 3.0. Crystal Impact'
_computing_publication_material  'Windows Word 2003'
_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     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4066
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2188
_refine_ls_R_factor_gt           0.2135
_refine_ls_wR_factor_ref         0.5745
_refine_ls_wR_factor_gt          0.5628
_refine_ls_goodness_of_fit_ref   3.089
_refine_ls_restrained_S_all      3.089
_refine_ls_shift/su_max          0.198
_refine_ls_shift/su_mean         0.028

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 0.14165(7) 0.40920(11) 0.06848(5) 0.0338(7) Uani 1 1 d . . . . .
O3 O 0.5487(5) 0.0008(7) 0.0966(3) 0.0456(18) Uani 1 1 d . . . . .
O1 O 0.2202(5) 0.3284(7) 0.1219(3) 0.0452(18) Uani 1 1 d . . . . .
N2 N 0.1757(5) 0.4652(7) 0.5108(3) 0.0310(16) Uani 1 1 d . . . . .
N1 N 0.2489(5) 0.0493(7) 0.2964(3) 0.0313(16) Uani 1 1 d . . . . .
C7 C 0.3122(7) 0.0145(9) 0.2069(4) 0.036(2) Uani 1 1 d . . . . .
O2 O 0.3078(6) 0.2987(9) 0.0580(3) 0.060(3) Uani 1 1 d . . . . .
C16 C 0.2602(8) 0.3950(11) 0.4398(5) 0.045(2) Uani 1 1 d . . . . .
H16 H 0.309631 0.404788 0.420109 0.054 Uiso 1 1 calc R U . . .
C3 C 0.3969(6) 0.1135(9) 0.1220(4) 0.0302(18) Uani 1 1 d . . . . .
H3 H 0.426256 0.147895 0.092923 0.036 Uiso 1 1 calc R U . . .
C2 C 0.3201(5) 0.1663(8) 0.1354(3) 0.0288(17) Uani 1 1 d . . . . .
C14 C 0.2192(6) 0.2127(8) 0.3814(3) 0.0319(18) Uani 1 1 d . . . . .
C6 C 0.3880(6) -0.0370(9) 0.1931(4) 0.0346(19) Uani 1 1 d . . . . .
H6 H 0.411098 -0.106697 0.213175 0.041 Uiso 1 1 calc R U . . .
C8 C 0.2769(6) 0.1168(10) 0.1777(4) 0.0343(19) Uani 1 1 d . . . . .
H8 H 0.224092 0.151601 0.186759 0.041 Uiso 1 1 calc R U . . .
C13 C 0.1562(6) 0.1269(11) 0.3610(4) 0.041(2) Uani 1 1 d . . . . .
H13 H 0.102389 0.124005 0.376268 0.049 Uiso 1 1 calc R U . . .
C19 C 0.1202(7) 0.3690(11) 0.4979(5) 0.043(2) Uani 1 1 d . . . . .
H19 H 0.071818 0.359129 0.518598 0.052 Uiso 1 1 calc R U . . .
C15 C 0.2027(6) 0.2993(9) 0.4254(4) 0.0327(18) Uani 1 1 d . . . . .
C9 C 0.2633(7) -0.0442(9) 0.2528(4) 0.037(2) Uani 1 1 d . . . . .
H9A H 0.207585 -0.076223 0.237147 0.045 Uiso 1 1 calc R U . . .
H9B H 0.296293 -0.115508 0.269116 0.045 Uiso 1 1 calc R U . . .
C10 C 0.3100(8) 0.1305(12) 0.3142(4) 0.047(3) Uani 1 1 d . . . . .
H10 H 0.362848 0.132451 0.297757 0.056 Uiso 1 1 calc R U . . .
C5 C 0.5124(7) -0.0487(10) 0.1350(5) 0.043(2) Uani 1 1 d . . . . .
C1 C 0.2806(6) 0.2717(9) 0.1021(4) 0.0347(19) Uani 1 1 d . . . . .
C4 C 0.4308(6) 0.0110(8) 0.1507(4) 0.0317(18) Uani 1 1 d . . . . .
C11 C 0.1732(6) 0.0475(11) 0.3190(4) 0.041(2) Uani 1 1 d . . . . .
H11 H 0.130573 -0.009886 0.305500 0.049 Uiso 1 1 calc R U . . .
C17 C 0.1321(7) 0.2859(11) 0.4560(4) 0.044(2) Uani 1 1 d . . . . .
H17 H 0.092402 0.220270 0.448088 0.053 Uiso 1 1 calc R U . . .
C12 C 0.2960(6) 0.2093(11) 0.3556(4) 0.043(2) Uani 1 1 d . . . . .
H12 H 0.340340 0.265217 0.367917 0.052 Uiso 1 1 calc R U . . .
O4 O 0.5366(10) -0.1420(17) 0.1577(8) 0.145(9) Uani 1 1 d . . . . .
C18 C 0.2465(7) 0.4748(10) 0.4818(4) 0.043(2) Uani 1 1 d . . . . .
H18 H 0.287127 0.538522 0.491045 0.052 Uiso 1 1 calc R U . . .
O1W O 0.0914(5) 0.2758(8) 0.0182(3) 0.0487(19) Uani 1 1 d . . . . .
H1WA H 0.072(7) 0.187(10) 0.034(4) 0.02(2) Uiso 1 1 d . . . . .
H1WB H 0.153(6) 0.335(9) -0.003(4) 0.01(2) 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
Zn1 O3 1.929(7) 3_455 ?
Zn1 O1 1.934(7) . ?
Zn1 O1W 2.008(8) . ?
Zn1 N2 2.050(7) 6_565 ?
O3 C5 1.251(13) . ?
O1 C1 1.254(12) . ?
N2 C18 1.367(12) . ?
N2 C19 1.371(13) . ?
N1 C10 1.344(16) . ?
N1 C11 1.348(12) . ?
N1 C9 1.492(11) . ?
C7 C6 1.377(14) . ?
C7 C8 1.400(14) . ?
C7 C9 1.542(13) . ?
O2 C1 1.222(13) . ?
C16 C18 1.366(14) . ?
C16 C15 1.393(15) . ?
C3 C4 1.388(12) . ?
C3 C2 1.394(12) . ?
C2 C8 1.385(13) . ?
C2 C1 1.500(12) . ?
C14 C12 1.404(12) . ?
C14 C13 1.414(14) . ?
C14 C15 1.458(12) . ?
C6 C4 1.378(13) . ?
C13 C11 1.376(14) . ?
C19 C17 1.381(14) . ?
C15 C17 1.391(13) . ?
C10 C12 1.348(14) . ?
C5 O4 1.193(16) . ?
C5 C4 1.508(13) . ?

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
O3 Zn1 O1 116.7(3) 3_455 . ?
O3 Zn1 O1W 107.9(4) 3_455 . ?
O1 Zn1 O1W 107.3(3) . . ?
O3 Zn1 N2 98.9(3) 3_455 6_565 ?
O1 Zn1 N2 125.0(3) . 6_565 ?
O1W Zn1 N2 99.0(3) . 6_565 ?
C5 O3 Zn1 116.8(7) . 3_545 ?
C1 O1 Zn1 114.7(6) . . ?
C18 N2 C19 117.8(8) . . ?
C18 N2 Zn1 124.9(7) . 6_566 ?
C19 N2 Zn1 117.2(6) . 6_566 ?
C10 N1 C11 120.4(8) . . ?
C10 N1 C9 121.6(8) . . ?
C11 N1 C9 117.9(9) . . ?
C6 C7 C8 120.4(9) . . ?
C6 C7 C9 120.1(8) . . ?
C8 C7 C9 119.4(9) . . ?
C18 C16 C15 121.0(10) . . ?
C4 C3 C2 120.5(8) . . ?
C8 C2 C3 120.1(8) . . ?
C8 C2 C1 119.3(8) . . ?
C3 C2 C1 120.5(8) . . ?
C12 C14 C13 115.2(8) . . ?
C12 C14 C15 123.7(9) . . ?
C13 C14 C15 121.1(8) . . ?
C7 C6 C4 120.9(8) . . ?
C2 C8 C7 118.9(8) . . ?
C11 C13 C14 119.8(8) . . ?
N2 C19 C17 122.4(9) . . ?
C17 C15 C16 117.9(9) . . ?
C17 C15 C14 121.6(9) . . ?
C16 C15 C14 120.5(9) . . ?
N1 C9 C7 110.9(7) . . ?
N1 C10 C12 119.8(10) . . ?
O4 C5 O3 123.9(10) . . ?
O4 C5 C4 119.0(10) . . ?
O3 C5 C4 117.0(9) . . ?
O2 C1 O1 123.4(9) . . ?
O2 C1 C2 120.0(9) . . ?
O1 C1 C2 116.6(8) . . ?
C6 C4 C3 119.1(8) . . ?
C6 C4 C5 120.4(8) . . ?
C3 C4 C5 120.5(9) . . ?
N1 C11 C13 121.6(10) . . ?
C19 C17 C15 119.4(9) . . ?
C10 C12 C14 123.2(10) . . ?
C16 C18 N2 121.5(10) . . ?

_refine_diff_density_max         11.323
_refine_diff_density_min         -1.243
_refine_diff_density_rms         0.514

