# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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. 
# 
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data_1541123
_database_code_depnum_ccdc_archive 'CCDC 1541123'
_audit_update_record             
;
2017-04-28 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C80 H66 Br4 N14 O8 Zn2'
_chemical_formula_weight         1801.84

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'
Br Br -0.2901 2.4595 '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      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c a'
_space_group_name_Hall           '-C 2bc 2'

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

_cell_length_a                   32.4215(6)
_cell_length_b                   9.5567(2)
_cell_length_c                   25.2788(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7832.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7212
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      28.16

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             3632
_exptl_transmission_factor_min   0.000
_exptl_transmission_factor_max   0.003
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    2.718
_shelx_estimated_absorpt_T_min   0.574
_shelx_estimated_absorpt_T_max   0.626
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.574
_exptl_absorpt_correction_T_max  0.626
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Breeze CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            59640
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_av_R_equivalents  0.0885
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.256
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3922
_reflns_number_gt                2609
_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 APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1708P)²+95.5321P] 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         3922
_refine_ls_number_parameters     243
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1249
_refine_ls_R_factor_gt           0.0873
_refine_ls_wR_factor_ref         0.2892
_refine_ls_wR_factor_gt          0.2458
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_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 0.0000 -0.10405(13) 0.36816(5) 0.0347(4) Uani 1 2 d S T P . .
Br1 Br 0.0000 -0.20745(14) 0.45282(5) 0.0506(4) Uani 1 2 d S T P . .
Br2 Br 0.0000 -0.21595(15) 0.28600(5) 0.0527(4) Uani 1 2 d S T P . .
O1 O 0.1090(2) 0.4163(6) 0.2815(2) 0.0459(15) Uani 1 1 d . . . . .
O2 O 0.14597(17) 0.3968(6) 0.0335(2) 0.0431(14) Uani 1 1 d . . . . .
N1 N 0.0478(2) 0.0386(7) 0.3698(2) 0.0358(15) Uani 1 1 d . . . . .
N2 N 0.10911(19) 0.2114(6) 0.2362(2) 0.0327(14) Uani 1 1 d . . . . .
H2B H 0.1061 0.1203 0.2396 0.039 Uiso 1 1 d R U . . .
C1 C 0.0625(3) 0.0822(9) 0.4167(3) 0.046(2) Uani 1 1 d . . . . .
H1A H 0.0532 0.0366 0.4479 0.055 Uiso 1 1 calc R U . . .
C2 C 0.0901(3) 0.1885(10) 0.4218(3) 0.055(3) Uani 1 1 d . . . . .
H2A H 0.1000 0.2151 0.4556 0.066 Uiso 1 1 calc R U . . .
C3 C 0.1036(3) 0.2577(10) 0.3765(3) 0.049(2) Uani 1 1 d . . . . .
H3A H 0.1221 0.3346 0.3791 0.059 Uiso 1 1 calc R U . . .
C4 C 0.0897(2) 0.2126(7) 0.3282(3) 0.0316(16) Uani 1 1 d . . . . .
C5 C 0.0618(2) 0.1033(8) 0.3261(3) 0.0333(16) Uani 1 1 d . . . . .
H5A H 0.0521 0.0728 0.2925 0.040 Uiso 1 1 calc R U . . .
C6 C 0.1036(2) 0.2896(8) 0.2797(3) 0.0353(18) Uani 1 1 d . . . . .
C7 C 0.1197(2) 0.2622(8) 0.1850(3) 0.0333(16) Uani 1 1 d . . . . .
C8 C 0.1036(3) 0.1944(8) 0.1417(3) 0.0354(18) Uani 1 1 d . . . . .
H8A H 0.0856 0.1171 0.1467 0.042 Uiso 1 1 calc R U . . .
C9 C 0.1134(2) 0.2374(9) 0.0912(3) 0.0360(17) Uani 1 1 d . . . . .
H9A H 0.1021 0.1904 0.0614 0.043 Uiso 1 1 calc R U . . .
C10 C 0.1398(2) 0.3505(8) 0.0845(3) 0.0344(17) Uani 1 1 d . . . . .
C11 C 0.1561(2) 0.4192(9) 0.1278(3) 0.0377(18) Uani 1 1 d . . . . .
H11A H 0.1741 0.4967 0.1230 0.045 Uiso 1 1 calc R U . . .
C12 C 0.1461(2) 0.3739(8) 0.1781(3) 0.0380(18) Uani 1 1 d . . . . .
H12A H 0.1574 0.4200 0.2080 0.046 Uiso 1 1 calc R U . . .
C13 C 0.1844(2) 0.4465(8) 0.0194(3) 0.0344(17) Uani 1 1 d . . . . .
C14 C 0.2208(2) 0.3945(9) 0.0374(3) 0.0381(18) Uani 1 1 d . . . . .
H14A H 0.2203 0.3214 0.0628 0.046 Uiso 1 1 calc R U . . .
C15 C 0.2587(5) 0.4444(15) 0.0200(5) 0.097(3) Uani 1 1 d . . . . .
C16 C 0.2965(3) 0.3955(10) 0.0376(3) 0.046(2) Uani 1 1 d . . . . .
H16A H 0.2972 0.3228 0.0632 0.055 Uiso 1 1 calc R U . . .
C17 C 0.3321(5) 0.4475(16) 0.0196(5) 0.095(3) Uani 1 1 d . . . . .
H17A H 0.3575 0.4136 0.0332 0.114 Uiso 1 1 calc R U . . .
N3 N 0.2865(4) 0.2135(12) 0.1813(4) 0.097(3) Uani 1 1 d . U . . .
C18 C 0.2899(5) 0.3715(16) 0.1833(6) 0.095(3) Uani 1 1 d . U . . .
C19 C 0.2887(6) 0.5377(17) 0.1770(7) 0.123(4) Uani 1 1 d . U . . .
H19A H 0.3045 0.5780 0.2053 0.147 Uiso 1 1 d R U . . .
H19B H 0.3011 0.5620 0.1437 0.147 Uiso 1 1 d R U . . .
H19C H 0.2610 0.5732 0.1782 0.147 Uiso 1 1 d R U . . .
N4 N 0.0638(6) 1.0000 0.0000 0.196(17) Uani 1 2 d S T P . .
C20 C 0.0398(8) 0.962(2) 0.0461(11) 0.079(9) Uani 0.5 1 d . . P . .
C21 C 0.0000 0.934(2) 0.0869(11) 0.132(9) Uani 1 2 d S T P . .
H21A H 0.0103 0.9001 0.1202 0.159 Uiso 0.5 1 d R U P . .
H21B H -0.0148 1.0196 0.0923 0.159 Uiso 0.5 1 d R U P . .
H21C H -0.0182 0.8652 0.0718 0.159 Uiso 0.5 1 d R U P . .


_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 N1 2.064(7) 11 ?
Zn1 N1 2.064(7) . ?
Zn1 Br2 2.3360(17) . ?
Zn1 Br1 2.3573(16) . ?
O1 C6 1.224(9) . ?
O2 C10 1.379(9) . ?
O2 C13 1.381(9) . ?
N1 C1 1.344(10) . ?
N1 C5 1.346(9) . ?
N2 C6 1.342(10) . ?
N2 C7 1.424(9) . ?
N2 H2B 0.8800 . ?
C1 C2 1.359(12) . ?
C1 H1A 0.9500 . ?
C2 C3 1.391(12) . ?
C2 H2A 0.9500 . ?
C3 C4 1.372(11) . ?
C3 H3A 0.9500 . ?
C4 C5 1.384(10) . ?
C4 C6 1.500(10) . ?
C5 H5A 0.9500 . ?
C7 C8 1.373(11) . ?
C7 C12 1.379(11) . ?
C8 C9 1.378(10) . ?
C8 H8A 0.9500 . ?
C9 C10 1.391(11) . ?
C9 H9A 0.9500 . ?
C10 C11 1.380(11) . ?
C11 C12 1.382(10) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C14 1.357(11) . ?
C13 C13 1.416(14) 3_565 ?
C14 C15 1.390(17) . ?
C14 H14A 0.9500 . ?
C15 C16 1.386(16) . ?
C15 C15 1.47(3) 3_565 ?
C16 C17 1.334(16) . ?
C16 H16A 0.9500 . ?
C17 C17 1.41(3) 3_565 ?
C17 H17A 0.9500 . ?
N3 C18 1.515(19) . ?
C18 C19 1.60(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9601 . ?
C19 H19C 0.9599 . ?
N4 C20 1.45(3) . ?
N4 C20 1.45(3) 3_575 ?
C20 C21 1.67(4) . ?
C21 C20 1.67(4) 11 ?
C21 H21A 0.9600 . ?
C21 H21B 0.9601 . ?
C21 H21C 0.9600 . ?

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
N1 Zn1 N1 97.3(4) 11 . ?
N1 Zn1 Br2 108.71(18) 11 . ?
N1 Zn1 Br2 108.71(18) . . ?
N1 Zn1 Br1 104.96(17) 11 . ?
N1 Zn1 Br1 104.96(17) . . ?
Br2 Zn1 Br1 127.97(8) . . ?
C10 O2 C13 118.8(6) . . ?
C1 N1 C5 117.6(7) . . ?
C1 N1 Zn1 119.3(5) . . ?
C5 N1 Zn1 122.6(5) . . ?
C6 N2 C7 125.9(6) . . ?
C6 N2 H2B 117.1 . . ?
C7 N2 H2B 116.9 . . ?
N1 C1 C2 123.2(7) . . ?
N1 C1 H1A 118.4 . . ?
C2 C1 H1A 118.4 . . ?
C1 C2 C3 119.1(8) . . ?
C1 C2 H2A 120.5 . . ?
C3 C2 H2A 120.5 . . ?
C4 C3 C2 118.6(8) . . ?
C4 C3 H3A 120.7 . . ?
C2 C3 H3A 120.7 . . ?
C3 C4 C5 119.1(7) . . ?
C3 C4 C6 118.4(7) . . ?
C5 C4 C6 122.4(6) . . ?
N1 C5 C4 122.4(7) . . ?
N1 C5 H5A 118.8 . . ?
C4 C5 H5A 118.8 . . ?
O1 C6 N2 124.4(7) . . ?
O1 C6 C4 119.7(7) . . ?
N2 C6 C4 115.9(6) . . ?
C8 C7 C12 120.0(7) . . ?
C8 C7 N2 118.1(7) . . ?
C12 C7 N2 121.9(7) . . ?
C7 C8 C9 120.7(7) . . ?
C7 C8 H8A 119.6 . . ?
C9 C8 H8A 119.6 . . ?
C8 C9 C10 119.0(7) . . ?
C8 C9 H9A 120.5 . . ?
C10 C9 H9A 120.5 . . ?
O2 C10 C11 122.2(7) . . ?
O2 C10 C9 116.9(7) . . ?
C11 C10 C9 120.6(7) . . ?
C10 C11 C12 119.3(8) . . ?
C10 C11 H11A 120.3 . . ?
C12 C11 H11A 120.3 . . ?
C7 C12 C11 120.3(7) . . ?
C7 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C14 C13 O2 124.8(7) . . ?
C14 C13 C13 119.8(4) . 3_565 ?
O2 C13 C13 115.3(4) . 3_565 ?
C13 C14 C15 122.4(8) . . ?
C13 C14 H14A 118.8 . . ?
C15 C14 H14A 118.8 . . ?
C16 C15 C14 124.5(11) . . ?
C16 C15 C15 117.7(7) . 3_565 ?
C14 C15 C15 117.8(6) . 3_565 ?
C17 C16 C15 121.9(11) . . ?
C17 C16 H16A 119.0 . . ?
C15 C16 H16A 119.0 . . ?
C16 C17 C17 120.3(7) . 3_565 ?
C16 C17 H17A 119.8 . . ?
C17 C17 H17A 119.8 3_565 . ?
N3 C18 C19 170.4(13) . . ?
C18 C19 H19A 108.1 . . ?
C18 C19 H19B 108.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 111.8 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 N4 C20 115(2) . 3_575 ?
N4 C20 C21 162.0(17) . . ?
C20 C21 C20 101(2) 11 . ?
C20 C21 H21A 149.4 11 . ?
C20 C21 H21A 109.1 . . ?
C20 C21 H21B 64.2 11 . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 52.6 11 . ?
C20 C21 H21C 110.0 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.9(14) . . . . ?
Zn1 N1 C1 C2 -171.3(8) . . . . ?
N1 C1 C2 C3 0.9(16) . . . . ?
C1 C2 C3 C4 -2.4(16) . . . . ?
C2 C3 C4 C5 2.1(14) . . . . ?
C2 C3 C4 C6 178.6(9) . . . . ?
C1 N1 C5 C4 -1.2(12) . . . . ?
Zn1 N1 C5 C4 170.8(6) . . . . ?
C3 C4 C5 N1 -0.3(12) . . . . ?
C6 C4 C5 N1 -176.7(7) . . . . ?
C7 N2 C6 O1 -3.7(13) . . . . ?
C7 N2 C6 C4 176.0(7) . . . . ?
C3 C4 C6 O1 -34.6(12) . . . . ?
C5 C4 C6 O1 141.7(8) . . . . ?
C3 C4 C6 N2 145.7(8) . . . . ?
C5 C4 C6 N2 -37.9(11) . . . . ?
C6 N2 C7 C8 -145.5(8) . . . . ?
C6 N2 C7 C12 36.1(12) . . . . ?
C12 C7 C8 C9 -0.4(12) . . . . ?
N2 C7 C8 C9 -178.9(7) . . . . ?
C7 C8 C9 C10 0.2(12) . . . . ?
C13 O2 C10 C11 40.7(11) . . . . ?
C13 O2 C10 C9 -144.7(7) . . . . ?
C8 C9 C10 O2 -174.9(7) . . . . ?
C8 C9 C10 C11 -0.1(12) . . . . ?
O2 C10 C11 C12 174.8(7) . . . . ?
C9 C10 C11 C12 0.4(12) . . . . ?
C8 C7 C12 C11 0.7(12) . . . . ?
N2 C7 C12 C11 179.1(7) . . . . ?
C10 C11 C12 C7 -0.6(13) . . . . ?
C10 O2 C13 C14 35.9(11) . . . . ?
C10 O2 C13 C13 -148.2(9) . . . 3_565 ?
O2 C13 C14 C15 177.0(10) . . . . ?
C13 C13 C14 C15 1.3(16) 3_565 . . . ?
C13 C14 C15 C16 179.5(11) . . . . ?
C13 C14 C15 C15 -1(2) . . . 3_565 ?
C14 C15 C16 C17 -179.9(12) . . . . ?
C15 C15 C16 C17 1(2) 3_565 . . . ?
C15 C16 C17 C17 -2(2) . . . 3_565 ?
C20 N4 C20 C21 -5(5) 3_575 . . . ?
N4 C20 C21 C20 6(6) . . . 11 ?

_refine_diff_density_max         3.123
_refine_diff_density_min         -1.890
_refine_diff_density_rms         0.196

####################################################################### 
# 
# 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_1541122
_database_code_depnum_ccdc_archive 'CCDC 1541122'
_audit_update_record             
;
2017-05-04 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C80 H66 Cl4 N14 O8 Zn2'
_chemical_formula_weight         1624.00

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'
Cl Cl 0.1484 0.1585 '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      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c a'
_space_group_name_Hall           '-C 2bc 2'

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

_cell_length_a                   32.2944(8)
_cell_length_b                   9.5094(2)
_cell_length_c                   25.2060(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7740.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7325
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.96

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             3344
_exptl_transmission_factor_min   0.000
_exptl_transmission_factor_max   0.003
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.823
_shelx_estimated_absorpt_T_min   0.840
_shelx_estimated_absorpt_T_max   0.859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_T_max  0.859
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Breeze CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48239
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_av_R_equivalents  0.0970
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.261
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3886
_reflns_number_gt                2767
_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 APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1454P)²+6.8488P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3886
_refine_ls_number_parameters     255
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0681
_refine_ls_wR_factor_ref         0.2219
_refine_ls_wR_factor_gt          0.1963
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.152
_refine_ls_shift/su_mean         0.013

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 0.0000 0.61728(7) 0.36789(3) 0.0385(3) Uani 1 2 d S T P . .
Cl1 Cl 0.0000 0.7223(2) 0.29029(8) 0.0580(5) Uani 1 2 d S T P . .
Cl2 Cl 0.0000 0.71112(19) 0.44869(7) 0.0568(5) Uani 1 2 d S T P . .
O1 O 0.10702(11) 0.0865(3) 0.28178(11) 0.0452(8) Uani 1 1 d . . . . .
O2 O 0.14596(9) 0.1052(3) 0.03327(11) 0.0419(8) Uani 1 1 d . . . . .
N1 N 0.04750(11) 0.4697(4) 0.36984(12) 0.0346(8) Uani 1 1 d . . . . .
N2 N 0.10750(10) 0.2930(3) 0.23629(12) 0.0330(8) Uani 1 1 d . . . . .
C1 C 0.06176(15) 0.4262(5) 0.41685(17) 0.0462(11) Uani 1 1 d . . . . .
H1A H 0.0530 0.4743 0.4479 0.055 Uiso 1 1 calc R U . . .
C2 C 0.08823(18) 0.3161(5) 0.42196(18) 0.0572(14) Uani 1 1 d . . . . .
H2A H 0.0976 0.2877 0.4560 0.069 Uiso 1 1 calc R U . . .
C3 C 0.10129(16) 0.2460(5) 0.37722(16) 0.0463(12) Uani 1 1 d . . . . .
H3A H 0.1196 0.1680 0.3800 0.056 Uiso 1 1 calc R U . . .
C4 C 0.08733(13) 0.2910(4) 0.32801(15) 0.0335(9) Uani 1 1 d . . . . .
C5 C 0.06078(12) 0.4048(4) 0.32589(15) 0.0310(9) Uani 1 1 d . . . . .
H5A H 0.0517 0.4379 0.2923 0.037 Uiso 1 1 calc R U . . .
C6 C 0.10151(12) 0.2137(4) 0.27920(15) 0.0321(9) Uani 1 1 d . . . . .
C7 C 0.11848(12) 0.2399(4) 0.18512(14) 0.0310(9) Uani 1 1 d . . . . .
C8 C 0.14544(13) 0.1288(4) 0.17869(16) 0.0353(9) Uani 1 1 d . . . . .
H8A H 0.1570 0.0838 0.2089 0.042 Uiso 1 1 calc R U . . .
C9 C 0.15564(13) 0.0828(5) 0.12840(15) 0.0383(10) Uani 1 1 d . . . . .
H9A H 0.1738 0.0050 0.1238 0.046 Uiso 1 1 calc R U . . .
C10 C 0.13921(12) 0.1512(5) 0.08467(15) 0.0362(9) Uani 1 1 d . . . . .
C11 C 0.11303(12) 0.2638(4) 0.09065(16) 0.0365(9) Uani 1 1 d . . . . .
H11A H 0.1026 0.3116 0.0603 0.044 Uiso 1 1 calc R U . . .
C12 C 0.10185(13) 0.3076(4) 0.14117(16) 0.0357(10) Uani 1 1 d . . . . .
H12A H 0.0830 0.3832 0.1457 0.043 Uiso 1 1 calc R U . . .
C13 C 0.18452(12) 0.0540(4) 0.01913(15) 0.0331(9) Uani 1 1 d . . . . .
C14 C 0.22081(13) 0.1068(4) 0.03804(16) 0.0375(10) Uani 1 1 d . . . . .
H14A H 0.2205 0.1796 0.0639 0.045 Uiso 1 1 calc R U . . .
C15 C 0.25892(12) 0.0534(4) 0.01926(15) 0.0365(9) Uani 1 1 d . . . . .
C16 C 0.29722(14) 0.1049(5) 0.03846(18) 0.0457(11) Uani 1 1 d . . . . .
H16A H 0.2977 0.1760 0.0649 0.055 Uiso 1 1 calc R U . . .
C17 C 0.33316(14) 0.0529(5) 0.01911(18) 0.0504(12) Uani 1 1 d . . . . .
H17A H 0.3587 0.0891 0.0317 0.060 Uiso 1 1 calc R U . . .
N3 N 0.2184(7) 0.7891(14) 0.1819(6) 0.357(16) Uani 1 1 d D . . . .
C19 C 0.2106(5) 0.4657(14) 0.1774(6) 0.214(8) Uani 1 1 d D . . . .
H19A H 0.1866 0.4245 0.1953 0.256 Uiso 1 1 calc R U . . .
H19B H 0.2098 0.4412 0.1397 0.256 Uiso 1 1 calc R U . . .
H19C H 0.2361 0.4287 0.1933 0.256 Uiso 1 1 calc R U . . .
C18 C 0.2095(3) 0.6404(17) 0.1841(4) 0.272(14) Uani 1 1 d D . . . .
N4 N 0.0630(3) 0.5000 0.0000 0.186(8) Uani 1 2 d S T P . .
C20 C 0.0394(4) 0.5362(12) 0.0451(7) 0.087(5) Uani 0.5 1 d . . P . .
C21 C 0.0000 0.5688(13) 0.0882(9) 0.176(8) Uani 1 2 d S T P . .
H21A H 0.0114 0.5998 0.1223 0.212 Uiso 0.5 1 calc R U P . .
H21B H -0.0179 0.6426 0.0738 0.212 Uiso 0.5 1 calc R U P . .
H21C H -0.0162 0.4827 0.0935 0.212 Uiso 0.5 1 calc R U P . .


_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 N1 2.079(3) . ?
Zn1 N1 2.079(3) 11 ?
Zn1 Cl1 2.1964(19) . ?
Zn1 Cl2 2.2236(17) . ?
O1 C6 1.224(5) . ?
O2 C10 1.385(5) . ?
O2 C13 1.384(5) . ?
N1 C1 1.337(5) . ?
N1 C5 1.339(5) . ?
N2 C6 1.333(5) . ?
N2 C7 1.430(5) . ?
C1 C2 1.358(7) . ?
C1 H1A 0.9500 . ?
C2 C3 1.376(6) . ?
C2 H2A 0.9500 . ?
C3 C4 1.388(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.382(5) . ?
C4 C6 1.505(5) . ?
C5 H5A 0.9500 . ?
C7 C8 1.379(5) . ?
C7 C12 1.389(5) . ?
C8 C9 1.381(5) . ?
C8 H8A 0.9500 . ?
C9 C10 1.386(6) . ?
C9 H9A 0.9500 . ?
C10 C11 1.373(6) . ?
C11 C12 1.387(6) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C14 1.361(6) . ?
C13 C13 1.408(8) 3 ?
C14 C15 1.413(6) . ?
C14 H14A 0.9500 . ?
C15 C15 1.405(8) 3 ?
C15 C16 1.416(6) . ?
C16 C17 1.352(6) . ?
C16 H16A 0.9500 . ?
C17 C17 1.394(9) 3 ?
C17 H17A 0.9500 . ?
N3 C18 1.444(9) . ?
C19 C18 1.671(9) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
N4 C20 1.412(17) . ?
N4 C20 1.412(17) 3_565 ?
C20 C21 1.70(2) . ?
C21 C20 1.70(2) 11 ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
N1 Zn1 N1 95.1(2) . 11 ?
N1 Zn1 Cl1 109.14(10) . . ?
N1 Zn1 Cl1 109.14(10) 11 . ?
N1 Zn1 Cl2 104.42(9) . . ?
N1 Zn1 Cl2 104.42(9) 11 . ?
Cl1 Zn1 Cl2 129.29(8) . . ?
C10 O2 C13 119.6(3) . . ?
C1 N1 C5 118.7(4) . . ?
C1 N1 Zn1 118.9(3) . . ?
C5 N1 Zn1 121.9(3) . . ?
C6 N2 C7 124.6(3) . . ?
N1 C1 C2 122.7(4) . . ?
N1 C1 H1A 118.7 . . ?
C2 C1 H1A 118.7 . . ?
C1 C2 C3 119.3(4) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 H2A 120.4 . . ?
C2 C3 C4 118.9(4) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 . . ?
C5 C4 C3 118.5(4) . . ?
C5 C4 C6 122.7(3) . . ?
C3 C4 C6 118.8(4) . . ?
N1 C5 C4 121.9(4) . . ?
N1 C5 H5A 119.1 . . ?
C4 C5 H5A 119.1 . . ?
O1 C6 N2 125.5(4) . . ?
O1 C6 C4 118.9(3) . . ?
N2 C6 C4 115.6(3) . . ?
C8 C7 C12 120.4(4) . . ?
C8 C7 N2 122.2(3) . . ?
C12 C7 N2 117.4(3) . . ?
C7 C8 C9 120.1(4) . . ?
C7 C8 H8A 120.0 . . ?
C9 C8 H8A 120.0 . . ?
C8 C9 C10 119.4(4) . . ?
C8 C9 H9A 120.3 . . ?
C10 C9 H9A 120.3 . . ?
C11 C10 O2 116.5(4) . . ?
C11 C10 C9 121.0(4) . . ?
O2 C10 C9 122.4(4) . . ?
C10 C11 C12 119.7(4) . . ?
C10 C11 H11A 120.2 . . ?
C12 C11 H11A 120.2 . . ?
C7 C12 C11 119.5(4) . . ?
C7 C12 H12A 120.2 . . ?
C11 C12 H12A 120.2 . . ?
C14 C13 O2 123.7(3) . . ?
C14 C13 C13 120.6(2) . 3 ?
O2 C13 C13 115.7(2) . 3 ?
C13 C14 C15 120.0(4) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C15 C15 C14 119.4(2) 3 . ?
C15 C15 C16 119.1(3) 3 . ?
C14 C15 C16 121.5(4) . . ?
C17 C16 C15 120.0(4) . . ?
C17 C16 H16A 120.0 . . ?
C15 C16 H16A 120.0 . . ?
C16 C17 C17 120.9(3) . 3 ?
C16 C17 H17A 119.6 . . ?
C17 C17 H17A 119.6 3 . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.4 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N3 C18 C19 164.9(12) . . ?
C20 N4 C20 114.4(12) . 3_565 ?
N4 C20 C21 164.5(11) . . ?
C20 C21 C20 96.6(14) . 11 ?
C20 C21 H21A 109.4 . . ?
C20 C21 H21A 153.8 11 . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21B 56.6 11 . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
C20 C21 H21C 62.5 11 . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -2.0(8) . . . . ?
Zn1 N1 C1 C2 170.1(4) . . . . ?
N1 C1 C2 C3 0.3(9) . . . . ?
C1 C2 C3 C4 0.7(8) . . . . ?
C2 C3 C4 C5 0.0(7) . . . . ?
C2 C3 C4 C6 -179.7(4) . . . . ?
C1 N1 C5 C4 2.7(6) . . . . ?
Zn1 N1 C5 C4 -169.2(3) . . . . ?
C3 C4 C5 N1 -1.7(6) . . . . ?
C6 C4 C5 N1 178.0(4) . . . . ?
C7 N2 C6 O1 4.8(7) . . . . ?
C7 N2 C6 C4 -176.0(3) . . . . ?
C5 C4 C6 O1 -145.2(4) . . . . ?
C3 C4 C6 O1 34.5(6) . . . . ?
C5 C4 C6 N2 35.6(6) . . . . ?
C3 C4 C6 N2 -144.7(4) . . . . ?
C6 N2 C7 C8 -37.8(6) . . . . ?
C6 N2 C7 C12 144.1(4) . . . . ?
C12 C7 C8 C9 -0.9(6) . . . . ?
N2 C7 C8 C9 -178.9(4) . . . . ?
C7 C8 C9 C10 1.3(7) . . . . ?
C13 O2 C10 C11 144.9(4) . . . . ?
C13 O2 C10 C9 -39.1(6) . . . . ?
C8 C9 C10 C11 0.1(7) . . . . ?
C8 C9 C10 O2 -175.7(4) . . . . ?
O2 C10 C11 C12 174.2(4) . . . . ?
C9 C10 C11 C12 -1.9(6) . . . . ?
C8 C7 C12 C11 -0.9(6) . . . . ?
N2 C7 C12 C11 177.2(3) . . . . ?
C10 C11 C12 C7 2.3(6) . . . . ?
C10 O2 C13 C14 -36.4(6) . . . . ?
C10 O2 C13 C13 146.9(5) . . . 3 ?
O2 C13 C14 C15 -176.5(4) . . . . ?
C13 C13 C14 C15 0.0(7) 3 . . . ?
C13 C14 C15 C15 0.5(7) . . . 3 ?
C13 C14 C15 C16 -179.3(4) . . . . ?
C15 C15 C16 C17 1.1(8) 3 . . . ?
C14 C15 C16 C17 -179.1(4) . . . . ?
C15 C16 C17 C17 -1.1(9) . . . 3 ?
C20 N4 C20 C21 2(3) 3_565 . . . ?
N4 C20 C21 C20 -3(4) . . . 11 ?

_refine_diff_density_max         0.946
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.124

####################################################################### 
# 
# 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_1541124
_database_code_depnum_ccdc_archive 'CCDC 1541124'
_audit_update_record             
;
2017-04-28 deposited with the CCDC.
2017-05-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C76 H60 I4 N12 O8 Zn2'
_chemical_formula_weight         1907.70

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'
I I -0.4742 1.8119 '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      orthorhombic
_space_group_IT_number           64
_space_group_name_H-M_alt        'C m c a'
_space_group_name_Hall           '-C 2bc 2'

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

_cell_length_a                   32.2573(4)
_cell_length_b                   9.35470(10)
_cell_length_c                   25.2417(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7616.87(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9862
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      26.25

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_F_000             3744
_exptl_transmission_factor_min   0.000
_exptl_transmission_factor_max   0.003
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    2.313
_shelx_estimated_absorpt_T_min   0.607
_shelx_estimated_absorpt_T_max   0.695
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.607
_exptl_absorpt_correction_T_max  0.695
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Breeze CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            60306
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.263
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4238
_reflns_number_gt                3276
_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 APEX2'
_computing_cell_refinement       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1427P)²+93.1184P] 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         4238
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0726
_refine_ls_wR_factor_ref         0.2358
_refine_ls_wR_factor_gt          0.2108
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.0000 -0.12924(12) 0.13256(4) 0.0316(3) Uani 1 2 d S T P . .
I1 I 0.0000 -0.27024(9) 0.04617(3) 0.0530(3) Uani 1 2 d S T P . .
I2 I 0.0000 -0.23926(9) 0.22308(3) 0.0476(3) Uani 1 2 d S T P . .
O1 O 0.11246(18) 0.4020(5) 0.21606(19) 0.0461(13) Uani 1 1 d . . . . .
O2 O 0.14701(16) 0.4001(6) 0.46432(18) 0.0442(12) Uani 1 1 d . . . . .
N1 N 0.04771(18) 0.0193(6) 0.12914(19) 0.0319(11) Uani 1 1 d . . . . .
N2 N 0.11306(17) 0.1945(6) 0.26176(19) 0.0300(11) Uani 1 1 d . . . . .
H2B H 0.1107 0.1012 0.2587 0.036 Uiso 1 1 d R U . . .
C1 C 0.0592(3) 0.0717(9) 0.0815(3) 0.0464(18) Uani 1 1 d . . . . .
H1A H 0.0484 0.0283 0.0504 0.056 Uiso 1 1 calc R U . . .
C2 C 0.0856(3) 0.1846(10) 0.0762(3) 0.061(3) Uani 1 1 d . . . . .
H2A H 0.0935 0.2181 0.0421 0.074 Uiso 1 1 calc R U . . .
C3 C 0.1008(4) 0.2492(12) 0.1215(4) 0.0634(18) Uani 1 1 d . . . . .
H3A H 0.1187 0.3298 0.1188 0.076 Uiso 1 1 calc R U . . .
C4 C 0.0900(5) 0.1962(15) 0.1705(5) 0.087(2) Uani 1 1 d . . . . .
C5 C 0.0636(2) 0.0807(7) 0.1726(2) 0.0303(12) Uani 1 1 d . . . . .
H5A H 0.0564 0.0428 0.2063 0.036 Uiso 1 1 calc R U . . .
C6 C 0.1061(2) 0.2739(7) 0.2185(3) 0.0331(14) Uani 1 1 d . . . . .
C7 C 0.1230(2) 0.2500(7) 0.3131(2) 0.0314(13) Uani 1 1 d . . . . .
C8 C 0.1504(2) 0.3635(8) 0.3187(3) 0.0381(15) Uani 1 1 d . . . . .
H8A H 0.1631 0.4055 0.2885 0.046 Uiso 1 1 calc R U . . .
C9 C 0.1590(2) 0.4147(9) 0.3692(3) 0.0402(16) Uani 1 1 d . . . . .
H9A H 0.1763 0.4959 0.3736 0.048 Uiso 1 1 calc R U . . .
C10 C 0.1421(2) 0.3471(8) 0.4131(2) 0.0366(15) Uani 1 1 d . . . . .
C11 C 0.1152(2) 0.2339(8) 0.4069(3) 0.0382(15) Uani 1 1 d . . . . .
H11A H 0.1031 0.1899 0.4372 0.046 Uiso 1 1 calc R U . . .
C12 C 0.1057(2) 0.1843(8) 0.3569(3) 0.0367(14) Uani 1 1 d . . . . .
H12A H 0.0874 0.1055 0.3525 0.044 Uiso 1 1 calc R U . . .
C13 C 0.1857(2) 0.4472(8) 0.4802(2) 0.0367(15) Uani 1 1 d . . . . .
C14 C 0.2217(2) 0.3963(8) 0.4603(3) 0.0415(16) Uani 1 1 d . . . . .
H14A H 0.2213 0.3264 0.4330 0.050 Uiso 1 1 calc R U . . .
C15 C 0.2605(2) 0.4476(8) 0.4805(3) 0.0375(15) Uani 1 1 d . . . . .
C16 C 0.2991(2) 0.3939(10) 0.4616(3) 0.0489(19) Uani 1 1 d . . . . .
H16A H 0.2994 0.3208 0.4355 0.059 Uiso 1 1 calc R U . . .
C17 C 0.3353(2) 0.4462(10) 0.4805(3) 0.0511(19) Uani 1 1 d . . . . .
H17A H 0.3609 0.4101 0.4674 0.061 Uiso 1 1 calc R U . . .
N3 N 0.2127(3) 0.5081(11) 0.1806(4) 0.087(2) Uani 1 1 d . . . . .
C18 C 0.2223(3) 0.3438(12) 0.1866(3) 0.0634(18) Uani 1 1 d . . . . .
C19 C 0.2350(7) 0.200(2) 0.1803(5) 0.177(12) Uani 1 1 d . . . . .
H19A H 0.2614 0.1991 0.1611 0.212 Uiso 1 1 d R U . A -1
H19B H 0.2143 0.1457 0.1603 0.212 Uiso 1 1 d R U . A -1
H19C H 0.2389 0.1559 0.2152 0.212 Uiso 1 1 d R U . A -1


_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 N1 2.075(6) . ?
Zn1 N1 2.075(6) 11 ?
Zn1 I2 2.5062(11) . ?
Zn1 I1 2.5484(12) . ?
O1 C6 1.217(8) . ?
O2 C13 1.383(9) . ?
O2 C10 1.393(7) . ?
N1 C5 1.341(8) . ?
N1 C1 1.351(8) . ?
N2 C6 1.339(9) . ?
N2 C7 1.432(7) . ?
N2 H2B 0.8800 . ?
C1 C2 1.363(12) . ?
C1 H1A 0.9500 . ?
C2 C3 1.382(13) . ?
C2 H2A 0.9500 . ?
C3 C4 1.379(15) . ?
C3 H3A 0.9500 . ?
C4 C5 1.377(14) . ?
C4 C6 1.504(14) . ?
C5 H5A 0.9500 . ?
C7 C12 1.382(10) . ?
C7 C8 1.388(10) . ?
C8 C9 1.389(9) . ?
C8 H8A 0.9500 . ?
C9 C10 1.388(10) . ?
C9 H9A 0.9500 . ?
C10 C11 1.378(10) . ?
C11 C12 1.381(10) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C14 1.351(10) . ?
C13 C13 1.407(13) 3_566 ?
C14 C15 1.435(10) . ?
C14 H14A 0.9500 . ?
C15 C15 1.388(13) 3_566 ?
C15 C16 1.424(10) . ?
C16 C17 1.354(11) . ?
C16 H16A 0.9500 . ?
C17 C17 1.409(17) 3_566 ?
C17 H17A 0.9500 . ?
N3 C18 1.575(15) . ?
C18 C19 1.42(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
N1 Zn1 N1 95.7(3) . 11 ?
N1 Zn1 I2 108.23(14) . . ?
N1 Zn1 I2 108.23(14) 11 . ?
N1 Zn1 I1 108.11(14) . . ?
N1 Zn1 I1 108.11(14) 11 . ?
I2 Zn1 I1 124.58(5) . . ?
C13 O2 C10 119.0(5) . . ?
C5 N1 C1 117.9(6) . . ?
C5 N1 Zn1 122.5(4) . . ?
C1 N1 Zn1 118.9(5) . . ?
C6 N2 C7 125.1(6) . . ?
C6 N2 H2B 117.6 . . ?
C7 N2 H2B 117.3 . . ?
N1 C1 C2 122.6(6) . . ?
N1 C1 H1A 118.7 . . ?
C2 C1 H1A 118.7 . . ?
C1 C2 C3 118.7(7) . . ?
C1 C2 H2A 120.6 . . ?
C3 C2 H2A 120.6 . . ?
C4 C3 C2 119.7(11) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C5 C4 C3 118.3(11) . . ?
C5 C4 C6 124.1(10) . . ?
C3 C4 C6 117.5(11) . . ?
N1 C5 C4 122.8(7) . . ?
N1 C5 H5A 118.6 . . ?
C4 C5 H5A 118.6 . . ?
O1 C6 N2 124.0(6) . . ?
O1 C6 C4 119.5(8) . . ?
N2 C6 C4 116.5(7) . . ?
C12 C7 C8 121.0(6) . . ?
C12 C7 N2 118.1(6) . . ?
C8 C7 N2 120.9(6) . . ?
C7 C8 C9 119.0(7) . . ?
C7 C8 H8A 120.5 . . ?
C9 C8 H8A 120.5 . . ?
C10 C9 C8 119.8(7) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C11 C10 C9 120.4(6) . . ?
C11 C10 O2 116.8(6) . . ?
C9 C10 O2 122.3(7) . . ?
C10 C11 C12 120.1(7) . . ?
C10 C11 H11A 119.9 . . ?
C12 C11 H11A 119.9 . . ?
C11 C12 C7 119.6(7) . . ?
C11 C12 H12A 120.2 . . ?
C7 C12 H12A 120.2 . . ?
C14 C13 O2 123.8(6) . . ?
C14 C13 C13 120.8(4) . 3_566 ?
O2 C13 C13 115.4(3) . 3_566 ?
C13 C14 C15 120.0(6) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C15 C15 C16 119.1(4) 3_566 . ?
C15 C15 C14 119.2(4) 3_566 . ?
C16 C15 C14 121.7(6) . . ?
C17 C16 C15 120.6(7) . . ?
C17 C16 H16A 119.7 . . ?
C15 C16 H16A 119.7 . . ?
C16 C17 C17 120.3(5) . 3_566 ?
C16 C17 H17A 119.8 . . ?
C17 C17 H17A 119.8 3_566 . ?
C19 C18 N3 166.7(10) . . ?
C18 C19 H19A 108.3 . . ?
C18 C19 H19B 110.6 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.9(13) . . . . ?
Zn1 N1 C1 C2 169.8(8) . . . . ?
N1 C1 C2 C3 -0.9(16) . . . . ?
C1 C2 C3 C4 1.9(19) . . . . ?
C2 C3 C4 C5 -1(2) . . . . ?
C2 C3 C4 C6 -177.7(10) . . . . ?
C1 N1 C5 C4 1.9(12) . . . . ?
Zn1 N1 C5 C4 -168.5(8) . . . . ?
C3 C4 C5 N1 -0.9(17) . . . . ?
C6 C4 C5 N1 175.6(9) . . . . ?
C7 N2 C6 O1 9.6(11) . . . . ?
C7 N2 C6 C4 -171.4(8) . . . . ?
C5 C4 C6 O1 -146.8(11) . . . . ?
C3 C4 C6 O1 29.8(16) . . . . ?
C5 C4 C6 N2 34.1(16) . . . . ?
C3 C4 C6 N2 -149.4(11) . . . . ?
C6 N2 C7 C12 140.8(7) . . . . ?
C6 N2 C7 C8 -41.3(10) . . . . ?
C12 C7 C8 C9 -2.7(11) . . . . ?
N2 C7 C8 C9 179.5(6) . . . . ?
C7 C8 C9 C10 3.7(11) . . . . ?
C8 C9 C10 C11 -3.3(12) . . . . ?
C8 C9 C10 O2 -175.0(7) . . . . ?
C13 O2 C10 C11 143.5(7) . . . . ?
C13 O2 C10 C9 -44.5(10) . . . . ?
C9 C10 C11 C12 1.8(11) . . . . ?
O2 C10 C11 C12 173.9(6) . . . . ?
C10 C11 C12 C7 -0.7(11) . . . . ?
C8 C7 C12 C11 1.2(11) . . . . ?
N2 C7 C12 C11 179.1(6) . . . . ?
C10 O2 C13 C14 -28.2(11) . . . . ?
C10 O2 C13 C13 152.7(8) . . . 3_566 ?
O2 C13 C14 C15 -177.7(7) . . . . ?
C13 C13 C14 C15 1.3(13) 3_566 . . . ?
C13 C14 C15 C15 -1.7(13) . . . 3_566 ?
C13 C14 C15 C16 178.4(8) . . . . ?
C15 C15 C16 C17 -1.3(14) 3_566 . . . ?
C14 C15 C16 C17 178.6(8) . . . . ?
C15 C16 C17 C17 0.5(16) . . . 3_566 ?

_refine_diff_density_max         3.903
_refine_diff_density_min         -2.470
_refine_diff_density_rms         0.241

