# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_14
_audit_block_doi                 10.5517/cc1j5j3b
_database_code_depnum_ccdc_archive 'CCDC 1405481'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H12 Cl2 O12 Zn3, 2(C6 H11 N2)'
_chemical_formula_sum            'C36 H34 Cl2 N4 O12 Zn3'
_chemical_formula_weight         981.68

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   12.7216(7)
_cell_length_b                   9.4960(7)
_cell_length_c                   18.0900(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.228(7)
_cell_angle_gamma                90.00
_cell_volume                     2075.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3346
_cell_measurement_theta_min      3.9900
_cell_measurement_theta_max      29.1420

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             996
_exptl_absorpt_coefficient_mu    1.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_T_max  0.826
_exptl_absorpt_process_details   'Sphere (CrystalClear)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating-anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7356
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_sigmaI/netI    0.1249
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.43
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3626
_reflns_number_gt                2561
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Corp., 2002)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2002)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2002)'
_computing_structure_solution    'Siemens SHELXTLTM 5'
_computing_structure_refinement  'Siemens SHELXTLTM 5'
_computing_molecular_graphics    'Siemens SHELXTLTM 5'
_computing_publication_material  'Siemens SHELXTLTM 5'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0316P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3626
_refine_ls_number_parameters     259
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0605
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.79669(5) 0.95994(8) 0.07309(3) 0.0197(2) Uani 1 1 d . . .
Zn2 Zn 1.0000 1.0000 0.0000 0.0174(3) Uani 1 2 d S . .
Cl1 Cl 0.66224(14) 0.8481(3) 0.10191(11) 0.0580(6) Uani 1 1 d . . .
O11 O 1.1300(3) 0.8744(5) 0.0530(2) 0.0366(12) Uani 1 1 d . . .
O12 O 1.2765(3) 0.9163(5) 0.0142(2) 0.0376(12) Uani 1 1 d . . .
O13 O 1.4728(3) 0.5838(5) 0.3914(2) 0.0372(12) Uani 1 1 d . . .
O14 O 1.6104(3) 0.5704(5) 0.3399(2) 0.0309(11) Uani 1 1 d . . .
C11 C 1.3017(4) 0.7925(7) 0.1312(3) 0.0270(15) Uani 1 1 d . . .
C12 C 1.4144(5) 0.7769(8) 0.1411(3) 0.0382(19) Uani 1 1 d . . .
H12A H 1.4436 0.8087 0.1030 0.046 Uiso 1 1 calc R . .
C13 C 1.4822(5) 0.7142(8) 0.2077(3) 0.0375(19) Uani 1 1 d . . .
H13A H 1.5573 0.7045 0.2142 0.045 Uiso 1 1 calc R . .
C14 C 1.4410(5) 0.6661(7) 0.2641(3) 0.0273(15) Uani 1 1 d . . .
C15 C 1.3292(4) 0.6796(9) 0.2526(3) 0.043(2) Uani 1 1 d . . .
H15A H 1.2996 0.6458 0.2901 0.051 Uiso 1 1 calc R . .
C16 C 1.2615(5) 0.7415(8) 0.1873(4) 0.041(2) Uani 1 1 d . . .
H16A H 1.1863 0.7492 0.1808 0.050 Uiso 1 1 calc R . .
C17 C 1.2304(5) 0.8657(7) 0.0606(3) 0.0269(15) Uani 1 1 d . . .
C18 C 1.5138(5) 0.6027(7) 0.3375(3) 0.0274(15) Uani 1 1 d . . .
O21 O 0.8906(3) 0.8440(4) 0.0283(2) 0.0238(9) Uani 1 1 d . . .
O22 O 0.9403(4) 0.7345(5) 0.1421(3) 0.0496(14) Uani 1 1 d . . .
C21 C 0.9684(5) 0.6173(7) 0.0360(4) 0.0313(15) Uani 1 1 d . . .
C22 C 1.0251(5) 0.5043(7) 0.0799(4) 0.0344(16) Uani 1 1 d . . .
H22A H 1.0420 0.5059 0.1338 0.041 Uiso 1 1 calc R . .
C23 C 1.0567(5) 0.3894(8) 0.0443(3) 0.0372(17) Uani 1 1 d . . .
H23A H 1.0953 0.3157 0.0747 0.045 Uiso 1 1 calc R . .
C24 C 0.9326(5) 0.7379(7) 0.0739(4) 0.0301(16) Uani 1 1 d . . .
N1 N 0.9417(7) 0.7680(9) 0.3540(4) 0.077(3) Uani 1 1 d . . .
N2 N 0.8042(7) 0.9037(10) 0.3316(5) 0.081(2) Uani 1 1 d . . .
C1 C 0.8778(8) 0.8521(12) 0.3021(5) 0.078(3) Uani 1 1 d . . .
H1A H 0.8834 0.8717 0.2531 0.093 Uiso 1 1 calc R . .
C2 C 0.8153(12) 0.8589(19) 0.4012(8) 0.137(6) Uani 1 1 d . . .
H2A H 0.7745 0.8833 0.4339 0.164 Uiso 1 1 calc R . .
C3 C 0.9006(13) 0.7682(16) 0.4145(7) 0.127(5) Uani 1 1 d . . .
H3A H 0.9275 0.7135 0.4591 0.153 Uiso 1 1 calc R . .
C4 C 0.7137(10) 1.0026(14) 0.2944(7) 0.136(5) Uani 1 1 d U . .
H4A H 0.6729 1.0232 0.3297 0.204 Uiso 1 1 calc R . .
H4B H 0.6651 0.9609 0.2479 0.204 Uiso 1 1 calc R . .
H4C H 0.7441 1.0882 0.2815 0.204 Uiso 1 1 calc R . .
C5 C 1.0353(11) 0.6953(18) 0.3478(8) 0.154(6) Uani 1 1 d . . .
H5A H 1.0413 0.6066 0.3753 0.185 Uiso 1 1 calc R . .
H5B H 1.0236 0.6739 0.2934 0.185 Uiso 1 1 calc R . .
C6 C 1.1365(12) 0.7687(19) 0.3772(10) 0.194(9) Uani 1 1 d . . .
H6A H 1.1961 0.7097 0.3740 0.291 Uiso 1 1 calc R . .
H6B H 1.1478 0.7937 0.4306 0.291 Uiso 1 1 calc R . .
H6C H 1.1342 0.8526 0.3472 0.291 Uiso 1 1 calc R . .


_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 O14 1.952(4) 2_755 ?
Zn1 O12 1.955(4) 3_775 ?
Zn1 O21 1.976(4) . ?
Zn1 Cl1 2.2096(18) . ?
Zn2 O11 2.021(4) . ?
Zn2 O11 2.021(4) 3_775 ?
Zn2 O13 2.046(4) 4_575 ?
Zn2 O13 2.046(4) 2_755 ?
Zn2 O21 2.200(4) 3_775 ?
Zn2 O21 2.200(4) . ?
O11 C17 1.244(6) . ?
O12 C17 1.260(7) . ?
O12 Zn1 1.955(4) 3_775 ?
O13 C18 1.254(7) . ?
O13 Zn2 2.046(4) 2_745 ?
O14 C18 1.253(6) . ?
O14 Zn1 1.952(4) 2_745 ?
C11 C16 1.360(8) . ?
C11 C12 1.396(7) . ?
C11 C17 1.487(8) . ?
C12 C13 1.377(8) . ?
C12 H12A 0.9300 . ?
C13 C14 1.363(8) . ?
C13 H13A 0.9300 . ?
C14 C15 1.378(7) . ?
C14 C18 1.488(7) . ?
C15 C16 1.358(8) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
O21 C24 1.306(7) . ?
O22 C24 1.206(7) . ?
C21 C23 1.387(8) 3_765 ?
C21 C22 1.395(8) . ?
C21 C24 1.479(9) . ?
C22 C23 1.389(9) . ?
C22 H22A 0.9300 . ?
C23 C21 1.387(8) 3_765 ?
C23 H23A 0.9300 . ?
N1 C1 1.305(11) . ?
N1 C3 1.354(15) . ?
N1 C5 1.410(14) . ?
N2 C1 1.309(11) . ?
N2 C2 1.295(13) . ?
N2 C4 1.476(12) . ?
C1 H1A 0.9300 . ?
C2 C3 1.347(16) . ?
C2 H2A 0.9300 . ?
C3 H3A 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.413(17) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 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
O14 Zn1 O12 110.1(2) 2_755 3_775 ?
O14 Zn1 O21 109.80(16) 2_755 . ?
O12 Zn1 O21 101.53(16) 3_775 . ?
O14 Zn1 Cl1 112.72(13) 2_755 . ?
O12 Zn1 Cl1 105.76(13) 3_775 . ?
O21 Zn1 Cl1 116.18(14) . . ?
O11 Zn2 O11 180.0 . 3_775 ?
O11 Zn2 O13 95.37(18) . 4_575 ?
O11 Zn2 O13 84.63(18) 3_775 4_575 ?
O11 Zn2 O13 84.63(18) . 2_755 ?
O11 Zn2 O13 95.37(18) 3_775 2_755 ?
O13 Zn2 O13 180.00(9) 4_575 2_755 ?
O11 Zn2 O21 91.41(15) . 3_775 ?
O11 Zn2 O21 88.59(15) 3_775 3_775 ?
O13 Zn2 O21 88.16(16) 4_575 3_775 ?
O13 Zn2 O21 91.84(16) 2_755 3_775 ?
O11 Zn2 O21 88.59(15) . . ?
O11 Zn2 O21 91.41(15) 3_775 . ?
O13 Zn2 O21 91.84(16) 4_575 . ?
O13 Zn2 O21 88.16(16) 2_755 . ?
O21 Zn2 O21 180.00(18) 3_775 . ?
C17 O11 Zn2 138.7(4) . . ?
C17 O12 Zn1 124.4(4) . 3_775 ?
C18 O13 Zn2 144.6(4) . 2_745 ?
C18 O14 Zn1 120.0(4) . 2_745 ?
C16 C11 C12 118.5(5) . . ?
C16 C11 C17 122.4(5) . . ?
C12 C11 C17 119.1(5) . . ?
C13 C12 C11 119.7(6) . . ?
C13 C12 H12A 120.2 . . ?
C11 C12 H12A 120.2 . . ?
C12 C13 C14 121.1(6) . . ?
C12 C13 H13A 119.4 . . ?
C14 C13 H13A 119.4 . . ?
C13 C14 C15 118.4(5) . . ?
C13 C14 C18 121.7(5) . . ?
C15 C14 C18 119.8(5) . . ?
C16 C15 C14 121.0(6) . . ?
C16 C15 H15A 119.5 . . ?
C14 C15 H15A 119.5 . . ?
C15 C16 C11 121.2(6) . . ?
C15 C16 H16A 119.4 . . ?
C11 C16 H16A 119.4 . . ?
O11 C17 O12 125.2(5) . . ?
O11 C17 C11 117.1(5) . . ?
O12 C17 C11 117.7(5) . . ?
O13 C18 O14 125.4(5) . . ?
O13 C18 C14 117.2(5) . . ?
O14 C18 C14 117.4(5) . . ?
C24 O21 Zn1 110.5(4) . . ?
C24 O21 Zn2 120.2(3) . . ?
Zn1 O21 Zn2 103.16(18) . . ?
C23 C21 C22 118.1(6) 3_765 . ?
C23 C21 C24 121.2(6) 3_765 . ?
C22 C21 C24 120.7(6) . . ?
C21 C22 C23 120.9(6) . . ?
C21 C22 H22A 119.6 . . ?
C23 C22 H22A 119.6 . . ?
C21 C23 C22 121.1(6) 3_765 . ?
C21 C23 H23A 119.5 3_765 . ?
C22 C23 H23A 119.5 . . ?
O22 C24 O21 123.6(6) . . ?
O22 C24 C21 121.1(6) . . ?
O21 C24 C21 115.4(6) . . ?
C1 N1 C3 105.6(10) . . ?
C1 N1 C5 126.4(10) . . ?
C3 N1 C5 127.9(12) . . ?
C1 N2 C2 113.6(10) . . ?
C1 N2 C4 127.4(10) . . ?
C2 N2 C4 119.0(12) . . ?
N2 C1 N1 107.4(8) . . ?
N2 C1 H1A 126.3 . . ?
N1 C1 H1A 126.3 . . ?
N2 C2 C3 102.7(12) . . ?
N2 C2 H2A 128.7 . . ?
C3 C2 H2A 128.7 . . ?
C2 C3 N1 110.5(11) . . ?
C2 C3 H3A 124.7 . . ?
N1 C3 H3A 124.7 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N1 114.9(14) . . ?
C6 C5 H5A 108.5 . . ?
N1 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
N1 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
O11 Zn2 O11 C17 -150(100) 3_775 . . . ?
O13 Zn2 O11 C17 78.5(6) 4_575 . . . ?
O13 Zn2 O11 C17 -101.5(6) 2_755 . . . ?
O21 Zn2 O11 C17 -9.8(6) 3_775 . . . ?
O21 Zn2 O11 C17 170.2(6) . . . . ?
C16 C11 C12 C13 -1.7(11) . . . . ?
C17 C11 C12 C13 177.5(7) . . . . ?
C11 C12 C13 C14 0.4(12) . . . . ?
C12 C13 C14 C15 1.0(11) . . . . ?
C12 C13 C14 C18 -177.8(6) . . . . ?
C13 C14 C15 C16 -1.1(11) . . . . ?
C18 C14 C15 C16 177.7(7) . . . . ?
C14 C15 C16 C11 -0.2(12) . . . . ?
C12 C11 C16 C15 1.6(11) . . . . ?
C17 C11 C16 C15 -177.6(7) . . . . ?
Zn2 O11 C17 O12 -24.1(11) . . . . ?
Zn2 O11 C17 C11 154.4(5) . . . . ?
Zn1 O12 C17 O11 8.1(10) 3_775 . . . ?
Zn1 O12 C17 C11 -170.4(4) 3_775 . . . ?
C16 C11 C17 O11 -2.6(10) . . . . ?
C12 C11 C17 O11 178.3(6) . . . . ?
C16 C11 C17 O12 176.0(7) . . . . ?
C12 C11 C17 O12 -3.1(10) . . . . ?
Zn2 O13 C18 O14 -4.4(13) 2_745 . . . ?
Zn2 O13 C18 C14 174.3(5) 2_745 . . . ?
Zn1 O14 C18 O13 8.5(9) 2_745 . . . ?
Zn1 O14 C18 C14 -170.2(4) 2_745 . . . ?
C13 C14 C18 O13 168.0(7) . . . . ?
C15 C14 C18 O13 -10.8(10) . . . . ?
C13 C14 C18 O14 -13.2(10) . . . . ?
C15 C14 C18 O14 168.0(6) . . . . ?
O14 Zn1 O21 C24 74.3(4) 2_755 . . . ?
O12 Zn1 O21 C24 -169.2(4) 3_775 . . . ?
Cl1 Zn1 O21 C24 -55.1(4) . . . . ?
O14 Zn1 O21 Zn2 -55.5(2) 2_755 . . . ?
O12 Zn1 O21 Zn2 61.00(19) 3_775 . . . ?
Cl1 Zn1 O21 Zn2 175.14(9) . . . . ?
O11 Zn2 O21 C24 8.3(5) . . . . ?
O11 Zn2 O21 C24 -171.7(5) 3_775 . . . ?
O13 Zn2 O21 C24 103.6(5) 4_575 . . . ?
O13 Zn2 O21 C24 -76.4(5) 2_755 . . . ?
O21 Zn2 O21 C24 -158(100) 3_775 . . . ?
O11 Zn2 O21 Zn1 131.89(18) . . . . ?
O11 Zn2 O21 Zn1 -48.11(18) 3_775 . . . ?
O13 Zn2 O21 Zn1 -132.78(18) 4_575 . . . ?
O13 Zn2 O21 Zn1 47.22(18) 2_755 . . . ?
O21 Zn2 O21 Zn1 -34(76) 3_775 . . . ?
C23 C21 C22 C23 0.8(11) 3_765 . . . ?
C24 C21 C22 C23 178.6(6) . . . . ?
C21 C22 C23 C21 -0.8(11) . . . 3_765 ?
Zn1 O21 C24 O22 -20.2(8) . . . . ?
Zn2 O21 C24 O22 99.8(7) . . . . ?
Zn1 O21 C24 C21 158.2(4) . . . . ?
Zn2 O21 C24 C21 -81.8(6) . . . . ?
C23 C21 C24 O22 169.3(6) 3_765 . . . ?
C22 C21 C24 O22 -8.4(10) . . . . ?
C23 C21 C24 O21 -9.2(9) 3_765 . . . ?
C22 C21 C24 O21 173.1(6) . . . . ?
C2 N2 C1 N1 0.2(14) . . . . ?
C4 N2 C1 N1 -179.4(10) . . . . ?
C3 N1 C1 N2 2.0(13) . . . . ?
C5 N1 C1 N2 -176.7(12) . . . . ?
C1 N2 C2 C3 -2.2(17) . . . . ?
C4 N2 C2 C3 177.3(11) . . . . ?
N2 C2 C3 N1 3.5(18) . . . . ?
C1 N1 C3 C2 -3.5(17) . . . . ?
C5 N1 C3 C2 175.2(14) . . . . ?
C1 N1 C5 C6 90.7(16) . . . . ?
C3 N1 C5 C6 -87.8(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         2.698
_refine_diff_density_min         -0.803
_refine_diff_density_rms         0.133




####################################################################### 
# 
# 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_14
_audit_block_doi                 10.5517/cc1j5j4c
_database_code_depnum_ccdc_archive 'CCDC 1405482'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H12 Cl2 O12 Zn3, 2(C7 H13 N2)'
_chemical_formula_sum            'C38 H38 Cl2 N4 O12 Zn3'
_chemical_formula_weight         1009.73

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   12.7659(6)
_cell_length_b                   9.5790(4)
_cell_length_c                   18.0520(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.206(5)
_cell_angle_gamma                90.00
_cell_volume                     2096.97(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7108
_cell_measurement_theta_min      3.3280
_cell_measurement_theta_max      28.3160

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1028
_exptl_absorpt_coefficient_mu    1.895
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83695
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Sphere (CrystalClear)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating-anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20009
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.43
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3683
_reflns_number_gt                3208
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Corp., 2002)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2002)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2002)'
_computing_structure_solution    'Siemens SHELXTLTM 5'
_computing_structure_refinement  'Siemens SHELXTLTM 5'
_computing_molecular_graphics    'Siemens SHELXTLTM 5'
_computing_publication_material  'Siemens SHELXTLTM 5'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3683
_refine_ls_number_parameters     268
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1373
_refine_ls_wR_factor_gt          0.1282
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.112
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.20046(3) 0.54207(4) 0.42560(2) 0.02106(18) Uani 1 1 d . . .
Zn2 Zn 0.0000 0.5000 0.5000 0.01972(19) Uani 1 2 d S . .
Cl1 Cl 0.33401(9) 0.64656(14) 0.39309(7) 0.0518(3) Uani 1 1 d . . .
O11 O 0.1080(2) 0.4278(3) 0.33952(14) 0.0321(6) Uani 1 1 d . . .
O12 O -0.0298(2) 0.4192(3) 0.39016(14) 0.0359(7) Uani 1 1 d . . .
O13 O -0.2229(2) 0.0751(3) 0.01539(14) 0.0360(7) Uani 1 1 d . . .
O14 O -0.3699(2) 0.1265(3) 0.05093(15) 0.0367(7) Uani 1 1 d . . .
C11 C -0.0609(3) 0.3288(4) 0.26524(19) 0.0271(8) Uani 1 1 d . . .
C12 C -0.0168(3) 0.2754(5) 0.2102(2) 0.0331(9) Uani 1 1 d . . .
H12A H 0.0584 0.2830 0.2179 0.040 Uiso 1 1 calc R . .
C13 C -0.0842(3) 0.2111(4) 0.1440(2) 0.0333(9) Uani 1 1 d . . .
H13A H -0.0539 0.1749 0.1075 0.040 Uiso 1 1 calc R . .
C14 C -0.1969(3) 0.1999(4) 0.13148(18) 0.0265(8) Uani 1 1 d . . .
C15 C -0.2409(3) 0.2558(5) 0.1865(2) 0.0371(10) Uani 1 1 d . . .
H15A H -0.3165 0.2515 0.1784 0.044 Uiso 1 1 calc R . .
C16 C -0.1728(3) 0.3175(5) 0.2528(2) 0.0405(11) Uani 1 1 d . . .
H16A H -0.2026 0.3522 0.2899 0.049 Uiso 1 1 calc R . .
C17 C 0.0108(3) 0.3978(4) 0.33762(19) 0.0261(8) Uani 1 1 d . . .
C18 C -0.2691(3) 0.1293(4) 0.0610(2) 0.0264(8) Uani 1 1 d . . .
O21 O 0.10760(18) 0.6569(3) 0.47127(12) 0.0239(5) Uani 1 1 d . . .
O22 O 0.0575(3) 0.7652(3) 0.35700(15) 0.0440(7) Uani 1 1 d . . .
C21 C 0.0302(3) 0.8842(4) 0.4646(2) 0.0266(8) Uani 1 1 d . . .
C22 C -0.0219(3) 0.9974(4) 0.4202(2) 0.0334(9) Uani 1 1 d . . .
H22A H -0.0367 0.9961 0.3664 0.040 Uiso 1 1 calc R . .
C23 C -0.0518(3) 1.1114(4) 0.4552(2) 0.0306(9) Uani 1 1 d . . .
H23A H -0.0870 1.1864 0.4248 0.037 Uiso 1 1 calc R . .
C24 C 0.0656(3) 0.7629(4) 0.4265(2) 0.0277(8) Uani 1 1 d . . .
N1 N 0.2016(4) 0.5963(5) 0.1686(3) 0.0662(12) Uani 1 1 d . . .
N2 N 0.0652(4) 0.7373(5) 0.1463(2) 0.0614(11) Uani 1 1 d . . .
C1 C 0.1249(5) 0.6432(7) 0.1967(3) 0.0657(15) Uani 1 1 d . . .
H1A H 0.1142 0.6158 0.2432 0.079 Uiso 1 1 calc R . .
C2 C 0.1892(7) 0.6631(9) 0.1003(4) 0.095(2) Uani 1 1 d . . .
H2A H 0.2320 0.6496 0.0677 0.114 Uiso 1 1 calc R . .
C3 C 0.1074(7) 0.7489(8) 0.0882(4) 0.086(2) Uani 1 1 d . . .
H3A H 0.0823 0.8088 0.0458 0.103 Uiso 1 1 calc R . .
C4 C 0.2830(6) 0.4883(9) 0.2029(5) 0.102(2) Uani 1 1 d . . .
H4A H 0.2741 0.4575 0.2512 0.153 Uiso 1 1 calc R . .
H4B H 0.3558 0.5256 0.2125 0.153 Uiso 1 1 calc R . .
H4C H 0.2725 0.4108 0.1676 0.153 Uiso 1 1 calc R . .
C5 C -0.0339(7) 0.8065(9) 0.1538(5) 0.110(3) Uani 1 1 d . . .
H5A H -0.0480 0.8911 0.1228 0.132 Uiso 1 1 calc R . .
H5B H -0.0216 0.8323 0.2078 0.132 Uiso 1 1 calc R . .
C6 C -0.1346(8) 0.7095(15) 0.1265(6) 0.171(4) Uani 1 1 d U . .
H6A H -0.1466 0.6769 0.1740 0.205 Uiso 1 1 calc R . .
H6B H -0.1961 0.7708 0.1018 0.205 Uiso 1 1 calc R . .
C7 C -0.1512(11) 0.5929(13) 0.0785(7) 0.174(4) Uani 1 1 d U . .
H7A H -0.2209 0.5512 0.0751 0.261 Uiso 1 1 calc R . .
H7B H -0.0932 0.5267 0.0999 0.261 Uiso 1 1 calc R . .
H7C H -0.1510 0.6203 0.0274 0.261 Uiso 1 1 calc R . .


_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 O13 1.963(2) 4_666 ?
Zn1 O11 1.965(2) . ?
Zn1 O21 1.976(2) . ?
Zn1 Cl1 2.2086(11) . ?
Zn2 O14 2.029(2) 2_455 ?
Zn2 O14 2.029(2) 4_666 ?
Zn2 O12 2.050(2) 3_566 ?
Zn2 O12 2.050(2) . ?
Zn2 O21 2.205(2) . ?
Zn2 O21 2.205(2) 3_566 ?
O11 C17 1.264(4) . ?
O12 C17 1.232(4) . ?
O13 C18 1.264(4) . ?
O13 Zn1 1.963(2) 4_565 ?
O14 C18 1.243(4) . ?
O14 Zn2 2.029(2) 2_445 ?
C11 C16 1.378(5) . ?
C11 C12 1.383(5) . ?
C11 C17 1.495(5) . ?
C12 C13 1.381(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.388(5) . ?
C13 H13A 0.9300 . ?
C14 C15 1.393(5) . ?
C14 C18 1.481(5) . ?
C15 C16 1.373(5) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
O21 C24 1.304(4) . ?
O22 C24 1.226(4) . ?
C21 C23 1.387(5) 3_576 ?
C21 C22 1.388(5) . ?
C21 C24 1.491(5) . ?
C22 C23 1.374(5) . ?
C22 H22A 0.9300 . ?
C23 C21 1.387(5) 3_576 ?
C23 H23A 0.9300 . ?
N1 C1 1.314(7) . ?
N1 C2 1.354(8) . ?
N1 C4 1.460(8) . ?
N2 C3 1.325(7) . ?
N2 C1 1.337(7) . ?
N2 C5 1.472(9) . ?
C1 H1A 0.9300 . ?
C2 C3 1.292(10) . ?
C2 H2A 0.9300 . ?
C3 H3A 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.537(13) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.388(14) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
O13 Zn1 O11 110.83(13) 4_666 . ?
O13 Zn1 O21 100.54(10) 4_666 . ?
O11 Zn1 O21 110.47(10) . . ?
O13 Zn1 Cl1 104.59(9) 4_666 . ?
O11 Zn1 Cl1 111.42(8) . . ?
O21 Zn1 Cl1 118.16(8) . . ?
O14 Zn2 O14 180.000(1) 2_455 4_666 ?
O14 Zn2 O12 95.22(12) 2_455 3_566 ?
O14 Zn2 O12 84.78(12) 4_666 3_566 ?
O14 Zn2 O12 84.78(12) 2_455 . ?
O14 Zn2 O12 95.22(12) 4_666 . ?
O12 Zn2 O12 180.0 3_566 . ?
O14 Zn2 O21 88.16(10) 2_455 . ?
O14 Zn2 O21 91.84(10) 4_666 . ?
O12 Zn2 O21 91.66(10) 3_566 . ?
O12 Zn2 O21 88.34(10) . . ?
O14 Zn2 O21 91.84(10) 2_455 3_566 ?
O14 Zn2 O21 88.16(10) 4_666 3_566 ?
O12 Zn2 O21 88.34(10) 3_566 3_566 ?
O12 Zn2 O21 91.66(10) . 3_566 ?
O21 Zn2 O21 180.00(9) . 3_566 ?
C17 O11 Zn1 119.3(2) . . ?
C17 O12 Zn2 144.3(2) . . ?
C18 O13 Zn1 124.0(2) . 4_565 ?
C18 O14 Zn2 137.9(3) . 2_445 ?
C16 C11 C12 119.1(3) . . ?
C16 C11 C17 119.9(3) . . ?
C12 C11 C17 121.0(3) . . ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13A 119.7 . . ?
C14 C13 H13A 119.7 . . ?
C13 C14 C15 118.9(3) . . ?
C13 C14 C18 120.7(3) . . ?
C15 C14 C18 120.4(3) . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C15 C16 C11 121.2(3) . . ?
C15 C16 H16A 119.4 . . ?
C11 C16 H16A 119.4 . . ?
O12 C17 O11 126.0(3) . . ?
O12 C17 C11 117.1(3) . . ?
O11 C17 C11 116.9(3) . . ?
O14 C18 O13 124.6(3) . . ?
O14 C18 C14 118.3(3) . . ?
O13 C18 C14 117.1(3) . . ?
C24 O21 Zn1 111.0(2) . . ?
C24 O21 Zn2 120.7(2) . . ?
Zn1 O21 Zn2 102.57(11) . . ?
C23 C21 C22 118.8(3) 3_576 . ?
C23 C21 C24 121.0(3) 3_576 . ?
C22 C21 C24 120.1(3) . . ?
C23 C22 C21 120.5(4) . . ?
C23 C22 H22A 119.8 . . ?
C21 C22 H22A 119.8 . . ?
C22 C23 C21 120.7(3) . 3_576 ?
C22 C23 H23A 119.7 . . ?
C21 C23 H23A 119.7 3_576 . ?
O22 C24 O21 122.4(3) . . ?
O22 C24 C21 121.2(3) . . ?
O21 C24 C21 116.4(3) . . ?
C1 N1 C2 107.5(6) . . ?
C1 N1 C4 126.5(6) . . ?
C2 N1 C4 125.9(7) . . ?
C3 N2 C1 108.0(5) . . ?
C3 N2 C5 127.5(6) . . ?
C1 N2 C5 124.4(5) . . ?
N1 C1 N2 107.6(5) . . ?
N1 C1 H1A 126.2 . . ?
N2 C1 H1A 126.2 . . ?
C3 C2 N1 108.2(6) . . ?
C3 C2 H2A 125.9 . . ?
N1 C2 H2A 125.9 . . ?
C2 C3 N2 108.7(6) . . ?
C2 C3 H3A 125.7 . . ?
N2 C3 H3A 125.7 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C6 110.8(7) . . ?
N2 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C7 C6 C5 129.5(9) . . ?
C7 C6 H6A 104.9 . . ?
C5 C6 H6A 104.9 . . ?
C7 C6 H6B 104.9 . . ?
C5 C6 H6B 104.9 . . ?
H6A C6 H6B 105.8 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
O13 Zn1 O11 C17 86.5(3) 4_666 . . . ?
O21 Zn1 O11 C17 -24.1(3) . . . . ?
Cl1 Zn1 O11 C17 -157.5(2) . . . . ?
O14 Zn2 O12 C17 121.7(5) 2_455 . . . ?
O14 Zn2 O12 C17 -58.3(5) 4_666 . . . ?
O12 Zn2 O12 C17 -143(100) 3_566 . . . ?
O21 Zn2 O12 C17 33.4(5) . . . . ?
O21 Zn2 O12 C17 -146.6(5) 3_566 . . . ?
C16 C11 C12 C13 -0.4(6) . . . . ?
C17 C11 C12 C13 179.5(4) . . . . ?
C11 C12 C13 C14 0.4(7) . . . . ?
C12 C13 C14 C15 0.6(6) . . . . ?
C12 C13 C14 C18 -179.2(4) . . . . ?
C13 C14 C15 C16 -1.7(6) . . . . ?
C18 C14 C15 C16 178.1(4) . . . . ?
C14 C15 C16 C11 1.8(7) . . . . ?
C12 C11 C16 C15 -0.7(7) . . . . ?
C17 C11 C16 C15 179.3(4) . . . . ?
Zn2 O12 C17 O11 1.0(7) . . . . ?
Zn2 O12 C17 C11 -179.8(3) . . . . ?
Zn1 O11 C17 O12 -9.4(5) . . . . ?
Zn1 O11 C17 C11 171.3(2) . . . . ?
C16 C11 C17 O12 13.1(6) . . . . ?
C12 C11 C17 O12 -166.8(4) . . . . ?
C16 C11 C17 O11 -167.6(4) . . . . ?
C12 C11 C17 O11 12.5(5) . . . . ?
Zn2 O14 C18 O13 29.4(6) 2_445 . . . ?
Zn2 O14 C18 C14 -150.2(3) 2_445 . . . ?
Zn1 O13 C18 O14 -7.2(6) 4_565 . . . ?
Zn1 O13 C18 C14 172.5(2) 4_565 . . . ?
C13 C14 C18 O14 -177.3(4) . . . . ?
C15 C14 C18 O14 2.9(6) . . . . ?
C13 C14 C18 O13 3.0(5) . . . . ?
C15 C14 C18 O13 -176.7(4) . . . . ?
O13 Zn1 O21 C24 166.9(2) 4_666 . . . ?
O11 Zn1 O21 C24 -76.0(2) . . . . ?
Cl1 Zn1 O21 C24 53.9(2) . . . . ?
O13 Zn1 O21 Zn2 -62.86(12) 4_666 . . . ?
O11 Zn1 O21 Zn2 54.24(12) . . . . ?
Cl1 Zn1 O21 Zn2 -175.83(5) . . . . ?
O14 Zn2 O21 C24 -8.8(2) 2_455 . . . ?
O14 Zn2 O21 C24 171.2(2) 4_666 . . . ?
O12 Zn2 O21 C24 -104.0(3) 3_566 . . . ?
O12 Zn2 O21 C24 76.0(3) . . . . ?
O21 Zn2 O21 C24 -145(100) 3_566 . . . ?
O14 Zn2 O21 Zn1 -132.82(11) 2_455 . . . ?
O14 Zn2 O21 Zn1 47.18(11) 4_666 . . . ?
O12 Zn2 O21 Zn1 132.01(11) 3_566 . . . ?
O12 Zn2 O21 Zn1 -47.99(11) . . . . ?
O21 Zn2 O21 Zn1 91(100) 3_566 . . . ?
C23 C21 C22 C23 -0.3(6) 3_576 . . . ?
C24 C21 C22 C23 -178.1(3) . . . . ?
C21 C22 C23 C21 0.3(6) . . . 3_576 ?
Zn1 O21 C24 O22 20.5(4) . . . . ?
Zn2 O21 C24 O22 -99.5(4) . . . . ?
Zn1 O21 C24 C21 -157.9(2) . . . . ?
Zn2 O21 C24 C21 82.1(3) . . . . ?
C23 C21 C24 O22 -172.0(3) 3_576 . . . ?
C22 C21 C24 O22 5.8(6) . . . . ?
C23 C21 C24 O21 6.5(5) 3_576 . . . ?
C22 C21 C24 O21 -175.8(3) . . . . ?
C2 N1 C1 N2 0.3(7) . . . . ?
C4 N1 C1 N2 -177.6(5) . . . . ?
C3 N2 C1 N1 -1.1(7) . . . . ?
C5 N2 C1 N1 175.3(6) . . . . ?
C1 N1 C2 C3 0.5(8) . . . . ?
C4 N1 C2 C3 178.5(6) . . . . ?
N1 C2 C3 N2 -1.2(9) . . . . ?
C1 N2 C3 C2 1.4(8) . . . . ?
C5 N2 C3 C2 -174.8(7) . . . . ?
C3 N2 C5 C6 96.7(9) . . . . ?
C1 N2 C5 C6 -78.9(9) . . . . ?
N2 C5 C6 C7 -20.1(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.482
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.119


####################################################################### 
# 
# 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_15
_audit_block_doi                 10.5517/cc1j5j5d
_database_code_depnum_ccdc_archive 'CCDC 1405483'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H6 O5 Zn'
_chemical_formula_sum            'C8 H6 O5 Zn'
_chemical_formula_weight         247.50

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc '

loop_
_symmetry_equiv_pos_as_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                   17.9537(10)
_cell_length_b                   6.3506(3)
_cell_length_c                   7.2542(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.419(5)
_cell_angle_gamma                90.00
_cell_volume                     826.85(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    732
_cell_measurement_theta_min      4.4050
_cell_measurement_theta_max      28.4820

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.988
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    2.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55466
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Sphere (CrystalClear)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating-anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1391
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.40
_diffrn_reflns_theta_max         25.01
_reflns_number_total             728
_reflns_number_gt                672
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Corp., 2002)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2002)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2002)'
_computing_structure_solution    'Siemens SHELXTLTM 5'
_computing_structure_refinement  'Siemens SHELXTLTM 5'
_computing_molecular_graphics    'Siemens SHELXTLTM 5'
_computing_publication_material  'Siemens SHELXTLTM 5'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0481P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         728
_refine_ls_number_parameters     71
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0740
_refine_ls_wR_factor_gt          0.0720
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.0000 0.31559(6) 0.7500 0.0161(2) Uani 1 2 d S . .
O11 O 0.04623(12) 0.2984(3) 0.4750(3) 0.0205(5) Uani 1 1 d . . .
O12 O 0.09569(11) 0.5767(3) 0.3395(3) 0.0276(5) Uani 1 1 d . . .
C11 C 0.17839(17) 0.3254(4) 0.4633(4) 0.0186(7) Uani 1 1 d . . .
C12 C 0.18946(18) 0.1269(5) 0.5442(4) 0.0225(7) Uani 1 1 d . . .
H12A H 0.1487 0.0444 0.5741 0.027 Uiso 1 1 calc R . .
C13 C 0.23968(16) 0.4456(4) 0.4207(4) 0.0208(6) Uani 1 1 d . . .
H13A H 0.2328 0.5777 0.3675 0.025 Uiso 1 1 calc R . .
C14 C 0.10156(15) 0.4040(4) 0.4251(3) 0.0171(6) Uani 1 1 d . . .
O1W O 0.0000 0.0044(5) 0.7500 0.0386(9) Uani 1 2 d S . .
H1W H -0.015(3) -0.083(8) 0.655(7) 0.074(14) 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 O12 1.946(2) 5_566 ?
Zn1 O12 1.946(2) 6_566 ?
Zn1 O1W 1.976(3) . ?
Zn1 O11 2.182(2) 2_556 ?
Zn1 O11 2.182(2) . ?
O11 C14 1.259(3) . ?
O12 C14 1.263(3) . ?
O12 Zn1 1.946(2) 5_566 ?
C11 C13 1.381(4) . ?
C11 C12 1.403(4) . ?
C11 C14 1.486(4) . ?
C12 C13 1.371(4) 7_556 ?
C12 H12A 0.9300 . ?
C13 C12 1.371(4) 7_556 ?
C13 H13A 0.9300 . ?
O1W H1W 0.92(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
O12 Zn1 O12 138.85(13) 5_566 6_566 ?
O12 Zn1 O1W 110.57(7) 5_566 . ?
O12 Zn1 O1W 110.57(6) 6_566 . ?
O12 Zn1 O11 88.27(8) 5_566 2_556 ?
O12 Zn1 O11 93.74(8) 6_566 2_556 ?
O1W Zn1 O11 87.14(5) . 2_556 ?
O12 Zn1 O11 93.74(8) 5_566 . ?
O12 Zn1 O11 88.27(8) 6_566 . ?
O1W Zn1 O11 87.14(5) . . ?
O11 Zn1 O11 174.28(10) 2_556 . ?
C14 O11 Zn1 123.86(17) . . ?
C14 O12 Zn1 122.09(19) . 5_566 ?
C13 C11 C12 119.0(3) . . ?
C13 C11 C14 120.9(2) . . ?
C12 C11 C14 120.1(3) . . ?
C13 C12 C11 120.1(3) 7_556 . ?
C13 C12 H12A 120.0 7_556 . ?
C11 C12 H12A 120.0 . . ?
C12 C13 C11 120.9(3) 7_556 . ?
C12 C13 H13A 119.5 7_556 . ?
C11 C13 H13A 119.5 . . ?
O11 C14 O12 123.2(3) . . ?
O11 C14 C11 120.2(2) . . ?
O12 C14 C11 116.7(2) . . ?
Zn1 O1W H1W 127(3) . . ?

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
O12 Zn1 O11 C14 117.0(2) 5_566 . . . ?
O12 Zn1 O11 C14 -21.8(2) 6_566 . . . ?
O1W Zn1 O11 C14 -132.5(2) . . . . ?
O11 Zn1 O11 C14 -132.5(2) 2_556 . . . ?
C13 C11 C12 C13 -0.2(5) . . . 7_556 ?
C14 C11 C12 C13 179.9(3) . . . 7_556 ?
C12 C11 C13 C12 0.2(5) . . . 7_556 ?
C14 C11 C13 C12 -179.9(3) . . . 7_556 ?
Zn1 O11 C14 O12 -96.0(3) . . . . ?
Zn1 O11 C14 C11 85.1(3) . . . . ?
Zn1 O12 C14 O11 -7.1(4) 5_566 . . . ?
Zn1 O12 C14 C11 171.85(17) 5_566 . . . ?
C13 C11 C14 O11 -175.6(2) . . . . ?
C12 C11 C14 O11 4.2(4) . . . . ?
C13 C11 C14 O12 5.4(4) . . . . ?
C12 C11 C14 O12 -174.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.105


####################################################################### 
# 
# 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_14
_audit_block_doi                 10.5517/cc1j5j6f
_database_code_depnum_ccdc_archive 'CCDC 1405484'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H12 Br2 O12 Zn3, 2(C6 H11 N2)'
_chemical_formula_sum            'C36 H34 Br2 N4 O12 Zn3'
_chemical_formula_weight         1070.60

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   12.9467(5)
_cell_length_b                   9.4171(3)
_cell_length_c                   18.3370(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.906(4)
_cell_angle_gamma                90.00
_cell_volume                     2115.04(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2294
_cell_measurement_theta_min      3.3850
_cell_measurement_theta_max      27.6830

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1068
_exptl_absorpt_coefficient_mu    3.639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.65156
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Sphere (CrystalClear)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating-anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8442
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0547
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.82
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3715
_reflns_number_gt                2951
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Corp., 2002)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2002)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2002)'
_computing_structure_solution    'Siemens SHELXTLTM 5'
_computing_structure_refinement  'Siemens SHELXTLTM 5'
_computing_molecular_graphics    'Siemens SHELXTLTM 5'
_computing_publication_material  'Siemens SHELXTLTM 5'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0638P)²+0.2639P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3715
_refine_ls_number_parameters     259
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1135
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.090
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.79992(4) 0.96435(6) 0.07148(3) 0.02568(18) Uani 1 1 d . . .
Zn2 Zn 1.0000 1.0000 0.0000 0.0237(2) Uani 1 2 d S . .
Br1 Br 0.65501(5) 0.84604(8) 0.09624(4) 0.0640(2) Uani 1 1 d . . .
O11 O 0.8903(3) 1.0733(4) 0.15951(18) 0.0388(8) Uani 1 1 d . . .
O12 O 1.0241(3) 1.0898(4) 0.10704(18) 0.0445(9) Uani 1 1 d . . .
O13 O 1.2300(3) 1.4065(4) 0.48557(18) 0.0419(9) Uani 1 1 d . . .
O14 O 1.3722(2) 1.3754(4) 0.44316(18) 0.0393(8) Uani 1 1 d . . .
C11 C 1.0609(4) 1.1680(5) 0.2339(2) 0.0329(11) Uani 1 1 d . . .
C12 C 1.1720(4) 1.1846(6) 0.2441(3) 0.0450(14) Uani 1 1 d . . .
H12A H 1.1995 1.1535 0.2059 0.054 Uiso 1 1 calc R . .
C13 C 1.2408(4) 1.2459(6) 0.3094(3) 0.0432(13) Uani 1 1 d . . .
H13A H 1.3143 1.2579 0.3151 0.052 Uiso 1 1 calc R . .
C14 C 1.2004(4) 1.2900(5) 0.3671(2) 0.0308(11) Uani 1 1 d . . .
C15 C 1.0908(4) 1.2739(6) 0.3579(3) 0.0437(13) Uani 1 1 d . . .
H15A H 1.0635 1.3056 0.3961 0.052 Uiso 1 1 calc R . .
C16 C 1.0215(4) 1.2106(6) 0.2920(3) 0.0458(14) Uani 1 1 d . . .
H16A H 0.9483 1.1969 0.2868 0.055 Uiso 1 1 calc R . .
C17 C 0.9869(4) 1.1053(5) 0.1614(2) 0.0313(11) Uani 1 1 d . . .
C18 C 1.2746(4) 1.3629(5) 0.4375(2) 0.0311(11) Uani 1 1 d . . .
O21 O 1.1088(2) 1.1543(3) -0.02758(17) 0.0291(7) Uani 1 1 d . . .
O22 O 1.0596(3) 1.2646(4) -0.1410(2) 0.0531(10) Uani 1 1 d . . .
C21 C 1.0316(4) 1.3838(5) -0.0349(3) 0.0333(11) Uani 1 1 d . . .
C22 C 1.0608(4) 1.3930(5) 0.0449(3) 0.0393(12) Uani 1 1 d . . .
H22A H 1.1015 1.3205 0.0754 0.047 Uiso 1 1 calc R . .
C23 C 0.9695(4) 1.4929(5) -0.0790(3) 0.0404(13) Uani 1 1 d . . .
H23A H 0.9484 1.4880 -0.1324 0.048 Uiso 1 1 calc R . .
C24 C 1.0671(4) 1.2627(5) -0.0721(3) 0.0346(11) Uani 1 1 d . . .
N1 N 0.8013(6) 0.9069(8) 0.3255(5) 0.100(2) Uani 1 1 d U . .
N2 N 0.9360(5) 0.7626(7) 0.3518(3) 0.0799(17) Uani 1 1 d . . .
C1 C 0.8769(7) 0.8505(10) 0.2985(4) 0.094(3) Uani 1 1 d . . .
H1A H 0.8860 0.8698 0.2512 0.112 Uiso 1 1 calc R . .
C2 C 0.8131(8) 0.8588(11) 0.3924(6) 0.101(3) Uani 1 1 d . . .
H2A H 0.7722 0.8850 0.4236 0.121 Uiso 1 1 calc R . .
C3 C 0.8940(9) 0.7647(10) 0.4103(4) 0.094(3) Uani 1 1 d . . .
H3A H 0.9174 0.7102 0.4549 0.113 Uiso 1 1 calc R . .
C4 C 0.7122(11) 0.9955(16) 0.2920(9) 0.195(6) Uani 1 1 d U . .
H4A H 0.6738 1.0122 0.3280 0.292 Uiso 1 1 calc R . .
H4B H 0.6640 0.9510 0.2465 0.292 Uiso 1 1 calc R . .
H4C H 0.7374 1.0843 0.2783 0.292 Uiso 1 1 calc R . .
C5 C 1.0312(9) 0.6791(15) 0.3499(7) 0.149(5) Uani 1 1 d . . .
H5A H 1.0406 0.5991 0.3848 0.179 Uiso 1 1 calc R . .
H5B H 1.0177 0.6418 0.2983 0.179 Uiso 1 1 calc R . .
C6 C 1.1275(10) 0.7592(18) 0.3709(8) 0.186(6) Uani 1 1 d . . .
H6A H 1.1871 0.7005 0.3688 0.279 Uiso 1 1 calc R . .
H6B H 1.1423 0.7946 0.4224 0.279 Uiso 1 1 calc R . .
H6C H 1.1192 0.8375 0.3360 0.279 Uiso 1 1 calc R . .


_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 O11 1.950(3) . ?
Zn1 O13 1.964(3) 4_585 ?
Zn1 O21 1.977(3) 3_775 ?
Zn1 Br1 2.3493(7) . ?
Zn2 O14 2.021(3) 4_585 ?
Zn2 O14 2.021(3) 2_745 ?
Zn2 O12 2.066(3) 3_775 ?
Zn2 O12 2.066(3) . ?
Zn2 O21 2.194(3) 3_775 ?
Zn2 O21 2.194(3) . ?
O11 C17 1.277(6) . ?
O12 C17 1.248(5) . ?
O13 C18 1.269(5) . ?
O13 Zn1 1.964(3) 4_686 ?
O14 C18 1.240(5) . ?
O14 Zn2 2.021(3) 2_755 ?
C11 C16 1.382(7) . ?
C11 C12 1.398(7) . ?
C11 C17 1.486(6) . ?
C12 C13 1.367(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.387(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.383(6) . ?
C14 C18 1.502(6) . ?
C15 C16 1.385(7) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
O21 C24 1.310(5) . ?
O21 Zn1 1.977(3) 3_775 ?
O22 C24 1.235(6) . ?
C21 C23 1.390(7) . ?
C21 C22 1.391(7) . ?
C21 C24 1.476(6) . ?
C22 C23 1.363(7) 3_785 ?
C22 H22A 0.9300 . ?
C23 C22 1.363(7) 3_785 ?
C23 H23A 0.9300 . ?
N1 C2 1.270(11) . ?
N1 C1 1.341(11) . ?
N1 C4 1.395(13) . ?
N2 C1 1.319(9) . ?
N2 C3 1.351(9) . ?
N2 C5 1.473(12) . ?
C1 H1A 0.9300 . ?
C2 C3 1.329(12) . ?
C2 H2A 0.9300 . ?
C3 H3A 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.400(15) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 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
O11 Zn1 O13 109.58(15) . 4_585 ?
O11 Zn1 O21 110.93(13) . 3_775 ?
O13 Zn1 O21 101.80(13) 4_585 3_775 ?
O11 Zn1 Br1 113.08(11) . . ?
O13 Zn1 Br1 105.02(10) 4_585 . ?
O21 Zn1 Br1 115.50(9) 3_775 . ?
O14 Zn2 O14 180.0 4_585 2_745 ?
O14 Zn2 O12 84.32(14) 4_585 3_775 ?
O14 Zn2 O12 95.68(14) 2_745 3_775 ?
O14 Zn2 O12 95.68(14) 4_585 . ?
O14 Zn2 O12 84.32(14) 2_745 . ?
O12 Zn2 O12 180.00(8) 3_775 . ?
O14 Zn2 O21 91.37(12) 4_585 3_775 ?
O14 Zn2 O21 88.63(12) 2_745 3_775 ?
O12 Zn2 O21 92.14(12) 3_775 3_775 ?
O12 Zn2 O21 87.86(12) . 3_775 ?
O14 Zn2 O21 88.63(12) 4_585 . ?
O14 Zn2 O21 91.37(12) 2_745 . ?
O12 Zn2 O21 87.86(12) 3_775 . ?
O12 Zn2 O21 92.14(12) . . ?
O21 Zn2 O21 180.00(14) 3_775 . ?
C17 O11 Zn1 117.8(3) . . ?
C17 O12 Zn2 145.9(3) . . ?
C18 O13 Zn1 124.2(3) . 4_686 ?
C18 O14 Zn2 137.8(3) . 2_755 ?
C16 C11 C12 119.0(4) . . ?
C16 C11 C17 120.9(4) . . ?
C12 C11 C17 120.1(4) . . ?
C13 C12 C11 121.0(4) . . ?
C13 C12 H12A 119.5 . . ?
C11 C12 H12A 119.5 . . ?
C12 C13 C14 119.6(4) . . ?
C12 C13 H13A 120.2 . . ?
C14 C13 H13A 120.2 . . ?
C15 C14 C13 120.1(4) . . ?
C15 C14 C18 120.0(4) . . ?
C13 C14 C18 119.9(4) . . ?
C14 C15 C16 120.2(4) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C11 C16 C15 120.1(5) . . ?
C11 C16 H16A 120.0 . . ?
C15 C16 H16A 120.0 . . ?
O12 C17 O11 125.4(4) . . ?
O12 C17 C11 117.2(4) . . ?
O11 C17 C11 117.4(4) . . ?
O14 C18 O13 126.3(4) . . ?
O14 C18 C14 117.8(4) . . ?
O13 C18 C14 115.9(4) . . ?
C24 O21 Zn1 111.5(3) . 3_775 ?
C24 O21 Zn2 119.6(3) . . ?
Zn1 O21 Zn2 103.44(13) 3_775 . ?
C23 C21 C22 118.3(4) . . ?
C23 C21 C24 120.7(4) . . ?
C22 C21 C24 121.0(4) . . ?
C23 C22 C21 120.8(5) 3_785 . ?
C23 C22 H22A 119.6 3_785 . ?
C21 C22 H22A 119.6 . . ?
C22 C23 C21 121.0(5) 3_785 . ?
C22 C23 H23A 119.5 3_785 . ?
C21 C23 H23A 119.5 . . ?
O22 C24 O21 122.0(4) . . ?
O22 C24 C21 121.9(4) . . ?
O21 C24 C21 116.1(4) . . ?
C2 N1 C1 110.0(8) . . ?
C2 N1 C4 117.5(11) . . ?
C1 N1 C4 132.3(11) . . ?
C1 N2 C3 107.1(8) . . ?
C1 N2 C5 127.4(8) . . ?
C3 N2 C5 125.5(9) . . ?
N2 C1 N1 107.0(7) . . ?
N2 C1 H1A 126.5 . . ?
N1 C1 H1A 126.5 . . ?
N1 C2 C3 108.3(8) . . ?
N1 C2 H2A 125.8 . . ?
C3 C2 H2A 125.8 . . ?
C2 C3 N2 107.5(7) . . ?
C2 C3 H3A 126.2 . . ?
N2 C3 H3A 126.2 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N2 112.5(11) . . ?
C6 C5 H5A 109.1 . . ?
N2 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
N2 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
O13 Zn1 O11 C17 -83.9(3) 4_585 . . . ?
O21 Zn1 O11 C17 27.7(4) 3_775 . . . ?
Br1 Zn1 O11 C17 159.3(3) . . . . ?
O14 Zn2 O12 C17 68.8(6) 4_585 . . . ?
O14 Zn2 O12 C17 -111.2(6) 2_745 . . . ?
O12 Zn2 O12 C17 -87(100) 3_775 . . . ?
O21 Zn2 O12 C17 -22.4(6) 3_775 . . . ?
O21 Zn2 O12 C17 157.6(6) . . . . ?
C16 C11 C12 C13 -1.9(8) . . . . ?
C17 C11 C12 C13 178.0(5) . . . . ?
C11 C12 C13 C14 1.2(9) . . . . ?
C12 C13 C14 C15 -1.0(8) . . . . ?
C12 C13 C14 C18 -177.4(5) . . . . ?
C13 C14 C15 C16 1.6(8) . . . . ?
C18 C14 C15 C16 178.0(5) . . . . ?
C12 C11 C16 C15 2.5(8) . . . . ?
C17 C11 C16 C15 -177.5(5) . . . . ?
C14 C15 C16 C11 -2.3(9) . . . . ?
Zn2 O12 C17 O11 -11.9(10) . . . . ?
Zn2 O12 C17 C11 168.8(4) . . . . ?
Zn1 O11 C17 O12 10.2(7) . . . . ?
Zn1 O11 C17 C11 -170.6(3) . . . . ?
C16 C11 C17 O12 169.2(5) . . . . ?
C12 C11 C17 O12 -10.8(7) . . . . ?
C16 C11 C17 O11 -10.1(7) . . . . ?
C12 C11 C17 O11 169.9(5) . . . . ?
Zn2 O14 C18 O13 -21.4(8) 2_755 . . . ?
Zn2 O14 C18 C14 158.2(3) 2_755 . . . ?
Zn1 O13 C18 O14 11.9(7) 4_686 . . . ?
Zn1 O13 C18 C14 -167.8(3) 4_686 . . . ?
C15 C14 C18 O14 -179.7(5) . . . . ?
C13 C14 C18 O14 -3.3(7) . . . . ?
C15 C14 C18 O13 0.0(7) . . . . ?
C13 C14 C18 O13 176.4(5) . . . . ?
O14 Zn2 O21 C24 -5.0(3) 4_585 . . . ?
O14 Zn2 O21 C24 175.0(3) 2_745 . . . ?
O12 Zn2 O21 C24 79.4(3) 3_775 . . . ?
O12 Zn2 O21 C24 -100.6(3) . . . . ?
O21 Zn2 O21 C24 80(100) 3_775 . . . ?
O14 Zn2 O21 Zn1 -129.71(15) 4_585 . . 3_775 ?
O14 Zn2 O21 Zn1 50.29(15) 2_745 . . 3_775 ?
O12 Zn2 O21 Zn1 -45.34(15) 3_775 . . 3_775 ?
O12 Zn2 O21 Zn1 134.66(15) . . . 3_775 ?
O21 Zn2 O21 Zn1 -44(100) 3_775 . . 3_775 ?
C23 C21 C22 C23 -0.9(9) . . . 3_785 ?
C24 C21 C22 C23 178.0(5) . . . 3_785 ?
C22 C21 C23 C22 0.9(9) . . . 3_785 ?
C24 C21 C23 C22 -178.0(5) . . . 3_785 ?
Zn1 O21 C24 O22 19.9(6) 3_775 . . . ?
Zn2 O21 C24 O22 -100.9(5) . . . . ?
Zn1 O21 C24 C21 -159.0(3) 3_775 . . . ?
Zn2 O21 C24 C21 80.2(4) . . . . ?
C23 C21 C24 O22 12.3(7) . . . . ?
C22 C21 C24 O22 -166.6(5) . . . . ?
C23 C21 C24 O21 -168.8(4) . . . . ?
C22 C21 C24 O21 12.3(7) . . . . ?
C3 N2 C1 N1 1.1(10) . . . . ?
C5 N2 C1 N1 -177.8(9) . . . . ?
C2 N1 C1 N2 0.9(11) . . . . ?
C4 N1 C1 N2 -173.6(11) . . . . ?
C1 N1 C2 C3 -2.6(12) . . . . ?
C4 N1 C2 C3 172.8(9) . . . . ?
N1 C2 C3 N2 3.2(12) . . . . ?
C1 N2 C3 C2 -2.6(10) . . . . ?
C5 N2 C3 C2 176.3(9) . . . . ?
C1 N2 C5 C6 80.8(13) . . . . ?
C3 N2 C5 C6 -97.8(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.122
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.111


####################################################################### 
# 
# 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_14
_audit_block_doi                 10.5517/cc1j5j7g
_database_code_depnum_ccdc_archive 'CCDC 1405485'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H12 Br2 O12 Zn3, 2(C7 H13 N2)'
_chemical_formula_sum            'C38 H38 Br2 N4 O12 Zn3'
_chemical_formula_weight         1098.65

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   13.0114(5)
_cell_length_b                   9.4909(4)
_cell_length_c                   18.3354(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.114(4)
_cell_angle_gamma                90.00
_cell_volume                     2139.41(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2732
_cell_measurement_theta_min      4.4170
_cell_measurement_theta_max      28.5410

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1100
_exptl_absorpt_coefficient_mu    3.600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.45976
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Sphere (CrystalClear)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating-anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8248
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.80
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3764
_reflns_number_gt                3145
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Corp., 2002)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2002)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2002)'
_computing_structure_solution    'Siemens SHELXTLTM 5'
_computing_structure_refinement  'Siemens SHELXTLTM 5'
_computing_molecular_graphics    'Siemens SHELXTLTM 5'
_computing_publication_material  'Siemens SHELXTLTM 5'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0583P)²+2.2536P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3764
_refine_ls_number_parameters     268
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1075
_refine_ls_wR_factor_gt          0.1004
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.074
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.80207(3) 0.03752(5) 0.07215(2) 0.01953(15) Uani 1 1 d . . .
Zn2 Zn 1.0000 0.0000 0.0000 0.01788(17) Uani 1 2 d S . .
Br1 Br 0.65754(4) 0.14895(7) 0.09989(3) 0.0534(2) Uani 1 1 d . . .
O11 O 1.1285(2) 0.1253(3) 0.05520(17) 0.0341(7) Uani 1 1 d . . .
O12 O 1.2704(2) 0.0863(3) 0.01526(16) 0.0348(8) Uani 1 1 d . . .
O13 O 1.4736(3) 0.4138(3) 0.39230(16) 0.0355(8) Uani 1 1 d . . .
O14 O 1.6070(2) 0.4262(3) 0.34083(16) 0.0324(7) Uani 1 1 d . . .
C11 C 1.3002(3) 0.2045(5) 0.1336(2) 0.0247(9) Uani 1 1 d . . .
C12 C 1.2594(3) 0.2544(5) 0.1894(2) 0.0347(11) Uani 1 1 d . . .
H12A H 1.1855 0.2463 0.1823 0.042 Uiso 1 1 calc R . .
C13 C 1.3278(3) 0.3158(6) 0.2555(3) 0.0371(12) Uani 1 1 d . . .
H13A H 1.2999 0.3496 0.2928 0.045 Uiso 1 1 calc R . .
C14 C 1.4388(3) 0.3278(4) 0.2668(2) 0.0254(9) Uani 1 1 d . . .
C15 C 1.4789(3) 0.2801(5) 0.2106(2) 0.0327(11) Uani 1 1 d . . .
H15A H 1.5525 0.2900 0.2170 0.039 Uiso 1 1 calc R . .
C16 C 1.4096(3) 0.2170(5) 0.1442(2) 0.0321(10) Uani 1 1 d . . .
H16A H 1.4373 0.1832 0.1068 0.038 Uiso 1 1 calc R . .
C17 C 1.2257(3) 0.1335(4) 0.0622(2) 0.0223(9) Uani 1 1 d . . .
C18 C 1.5117(3) 0.3949(4) 0.3393(2) 0.0242(9) Uani 1 1 d . . .
O21 O 0.8923(2) 0.1543(3) 0.02750(15) 0.0232(6) Uani 1 1 d . . .
O22 O 0.9385(3) 0.2667(4) 0.13989(18) 0.0466(9) Uani 1 1 d . . .
C21 C 0.9687(3) 0.3846(4) 0.0346(2) 0.0258(9) Uani 1 1 d . . .
C22 C 1.0241(4) 0.4959(5) 0.0791(3) 0.0322(10) Uani 1 1 d . . .
H22A H 1.0404 0.4935 0.1324 0.039 Uiso 1 1 calc R . .
C23 C 1.0551(4) 0.6097(5) 0.0451(2) 0.0301(10) Uani 1 1 d . . .
H23A H 1.0923 0.6839 0.0757 0.036 Uiso 1 1 calc R . .
C24 C 0.9334(3) 0.2632(5) 0.0719(2) 0.0273(9) Uani 1 1 d . . .
N1 N 1.8103(7) 0.1492(9) 0.3916(5) 0.114(3) Uani 1 1 d U . .
H1A H 1.7715 0.1277 0.4200 0.137 Uiso 1 1 calc R . .
N2 N 1.8705(6) 0.1550(8) 0.2993(4) 0.103(2) Uani 1 1 d U . .
H2A H 1.8780 0.1370 0.2553 0.123 Uiso 1 1 calc R . .
C1 C 1.7985(5) 0.0993(8) 0.3258(5) 0.0686(18) Uani 1 1 d U . .
C2 C 1.8942(7) 0.2424(9) 0.4108(4) 0.078(2) Uani 1 1 d . . .
H2B H 1.9203 0.2938 0.4563 0.094 Uiso 1 1 calc R . .
C3 C 1.9309(4) 0.2451(6) 0.3521(3) 0.0427(12) Uani 1 1 d U . .
C4 C 1.7196(11) -0.0034(15) 0.2974(8) 0.181(6) Uani 1 1 d . . .
H4A H 1.6810 -0.0180 0.3334 0.272 Uiso 1 1 calc R . .
H4B H 1.7537 -0.0898 0.2906 0.272 Uiso 1 1 calc R . .
H4C H 1.6696 0.0267 0.2488 0.272 Uiso 1 1 calc R . .
C5 C 2.0247(9) 0.3276(11) 0.3484(7) 0.123(3) Uani 1 1 d . . .
H5A H 2.0084 0.3674 0.2972 0.147 Uiso 1 1 calc R . .
H5B H 2.0376 0.4049 0.3850 0.147 Uiso 1 1 calc R . .
C6 C 2.1208(11) 0.2430(17) 0.3657(8) 0.162(5) Uani 1 1 d U . .
H6A H 2.1333 0.2344 0.3165 0.195 Uiso 1 1 calc R . .
H6B H 2.1782 0.3041 0.3968 0.195 Uiso 1 1 calc R . .
C7 C 2.1473(11) 0.1142(16) 0.3986(10) 0.187(5) Uani 1 1 d U . .
H7A H 2.2171 0.0864 0.3961 0.280 Uiso 1 1 calc R . .
H7B H 2.0934 0.0467 0.3714 0.280 Uiso 1 1 calc R . .
H7C H 2.1503 0.1183 0.4516 0.280 Uiso 1 1 calc R . .


_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 O14 1.956(3) 2_745 ?
Zn1 O12 1.962(3) 3_755 ?
Zn1 O21 1.976(3) . ?
Zn1 Br1 2.3537(6) . ?
Zn2 O11 2.032(3) . ?
Zn2 O11 2.032(3) 3_755 ?
Zn2 O13 2.060(3) 4_565 ?
Zn2 O13 2.060(3) 2_745 ?
Zn2 O21 2.196(3) 3_755 ?
Zn2 O21 2.196(3) . ?
O11 C17 1.230(5) . ?
O12 C17 1.268(5) . ?
O12 Zn1 1.962(3) 3_755 ?
O13 C18 1.240(5) . ?
O13 Zn2 2.060(3) 2_755 ?
O14 C18 1.267(5) . ?
O14 Zn1 1.956(3) 2_755 ?
C11 C16 1.377(6) . ?
C11 C12 1.383(6) . ?
C11 C17 1.509(5) . ?
C12 C13 1.376(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.395(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.375(6) . ?
C14 C18 1.499(5) . ?
C15 C16 1.391(6) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
O21 C24 1.317(5) . ?
O22 C24 1.227(5) . ?
C21 C22 1.384(6) . ?
C21 C23 1.393(6) 3_765 ?
C21 C24 1.487(6) . ?
C22 C23 1.373(6) . ?
C22 H22A 0.9300 . ?
C23 C21 1.393(6) 3_765 ?
C23 H23A 0.9300 . ?
N1 C1 1.258(10) . ?
N1 C2 1.359(10) . ?
N1 H1A 0.8600 . ?
N2 C1 1.301(10) . ?
N2 C3 1.337(8) . ?
N2 H2A 0.8600 . ?
C1 C4 1.387(14) . ?
C2 C3 1.312(8) . ?
C2 H2B 0.9300 . ?
C3 C5 1.470(10) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.432(16) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.357(17) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
O14 Zn1 O12 110.09(14) 2_745 3_755 ?
O14 Zn1 O21 110.99(12) 2_745 . ?
O12 Zn1 O21 100.90(12) 3_755 . ?
O14 Zn1 Br1 112.27(9) 2_745 . ?
O12 Zn1 Br1 103.97(9) 3_755 . ?
O21 Zn1 Br1 117.56(8) . . ?
O11 Zn2 O11 180.0(3) . 3_755 ?
O11 Zn2 O13 95.56(13) . 4_565 ?
O11 Zn2 O13 84.44(13) 3_755 4_565 ?
O11 Zn2 O13 84.44(13) . 2_745 ?
O11 Zn2 O13 95.56(13) 3_755 2_745 ?
O13 Zn2 O13 180.00(17) 4_565 2_745 ?
O11 Zn2 O21 91.23(11) . 3_755 ?
O11 Zn2 O21 88.77(11) 3_755 3_755 ?
O13 Zn2 O21 87.90(11) 4_565 3_755 ?
O13 Zn2 O21 92.10(11) 2_745 3_755 ?
O11 Zn2 O21 88.77(11) . . ?
O11 Zn2 O21 91.23(11) 3_755 . ?
O13 Zn2 O21 92.10(11) 4_565 . ?
O13 Zn2 O21 87.90(11) 2_745 . ?
O21 Zn2 O21 180.00(14) 3_755 . ?
C17 O11 Zn2 137.6(3) . . ?
C17 O12 Zn1 124.2(3) . 3_755 ?
C18 O13 Zn2 145.6(3) . 2_755 ?
C18 O14 Zn1 118.1(3) . 2_755 ?
C16 C11 C12 119.7(4) . . ?
C16 C11 C17 120.2(4) . . ?
C12 C11 C17 120.1(4) . . ?
C13 C12 C11 120.2(4) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C12 C13 C14 120.3(4) . . ?
C12 C13 H13A 119.9 . . ?
C14 C13 H13A 119.9 . . ?
C15 C14 C13 119.4(4) . . ?
C15 C14 C18 121.3(4) . . ?
C13 C14 C18 119.3(4) . . ?
C14 C15 C16 120.1(4) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C11 C16 C15 120.3(4) . . ?
C11 C16 H16A 119.8 . . ?
C15 C16 H16A 119.8 . . ?
O11 C17 O12 126.2(4) . . ?
O11 C17 C11 117.7(4) . . ?
O12 C17 C11 116.0(3) . . ?
O13 C18 O14 126.0(4) . . ?
O13 C18 C14 117.2(4) . . ?
O14 C18 C14 116.7(4) . . ?
C24 O21 Zn1 111.1(2) . . ?
C24 O21 Zn2 120.3(2) . . ?
Zn1 O21 Zn2 103.39(12) . . ?
C22 C21 C23 118.9(4) . 3_765 ?
C22 C21 C24 120.0(4) . . ?
C23 C21 C24 121.1(4) 3_765 . ?
C23 C22 C21 120.5(4) . . ?
C23 C22 H22A 119.8 . . ?
C21 C22 H22A 119.8 . . ?
C22 C23 C21 120.6(4) . 3_765 ?
C22 C23 H23A 119.7 . . ?
C21 C23 H23A 119.7 3_765 . ?
O22 C24 O21 121.7(4) . . ?
O22 C24 C21 121.6(4) . . ?
O21 C24 C21 116.6(4) . . ?
C1 N1 C2 109.1(7) . . ?
C1 N1 H1A 125.4 . . ?
C2 N1 H1A 125.4 . . ?
C1 N2 C3 108.2(7) . . ?
C1 N2 H2A 125.9 . . ?
C3 N2 H2A 125.9 . . ?
N1 C1 N2 109.2(7) . . ?
N1 C1 C4 117.8(10) . . ?
N2 C1 C4 132.8(10) . . ?
C3 C2 N1 106.2(6) . . ?
C3 C2 H2B 126.9 . . ?
N1 C2 H2B 126.9 . . ?
C2 C3 N2 107.2(6) . . ?
C2 C3 C5 125.3(7) . . ?
N2 C3 C5 127.4(7) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C3 111.6(9) . . ?
C6 C5 H5A 109.3 . . ?
C3 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C3 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C7 C6 C5 132.8(13) . . ?
C7 C6 H6A 104.0 . . ?
C5 C6 H6A 104.0 . . ?
C7 C6 H6B 104.0 . . ?
C5 C6 H6B 104.0 . . ?
H6A C6 H6B 105.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
O11 Zn2 O11 C17 -29(100) 3_755 . . . ?
O13 Zn2 O11 C17 -76.7(4) 4_565 . . . ?
O13 Zn2 O11 C17 103.3(4) 2_745 . . . ?
O21 Zn2 O11 C17 11.3(4) 3_755 . . . ?
O21 Zn2 O11 C17 -168.7(4) . . . . ?
C16 C11 C12 C13 -0.2(7) . . . . ?
C17 C11 C12 C13 178.3(4) . . . . ?
C11 C12 C13 C14 -0.3(8) . . . . ?
C12 C13 C14 C15 1.3(7) . . . . ?
C12 C13 C14 C18 -179.9(4) . . . . ?
C13 C14 C15 C16 -1.8(7) . . . . ?
C18 C14 C15 C16 179.4(4) . . . . ?
C12 C11 C16 C15 -0.3(7) . . . . ?
C17 C11 C16 C15 -178.8(4) . . . . ?
C14 C15 C16 C11 1.3(8) . . . . ?
Zn2 O11 C17 O12 24.1(7) . . . . ?
Zn2 O11 C17 C11 -155.0(3) . . . . ?
Zn1 O12 C17 O11 -10.0(6) 3_755 . . . ?
Zn1 O12 C17 C11 169.1(3) 3_755 . . . ?
C16 C11 C17 O11 -179.8(4) . . . . ?
C12 C11 C17 O11 1.7(6) . . . . ?
C16 C11 C17 O12 1.0(6) . . . . ?
C12 C11 C17 O12 -177.5(4) . . . . ?
Zn2 O13 C18 O14 6.2(8) 2_755 . . . ?
Zn2 O13 C18 C14 -174.3(4) 2_755 . . . ?
Zn1 O14 C18 O13 -8.9(6) 2_755 . . . ?
Zn1 O14 C18 C14 171.5(3) 2_755 . . . ?
C15 C14 C18 O13 -168.4(4) . . . . ?
C13 C14 C18 O13 12.8(6) . . . . ?
C15 C14 C18 O14 11.2(6) . . . . ?
C13 C14 C18 O14 -167.6(4) . . . . ?
O14 Zn1 O21 C24 -75.1(3) 2_745 . . . ?
O12 Zn1 O21 C24 168.3(3) 3_755 . . . ?
Br1 Zn1 O21 C24 56.1(3) . . . . ?
O14 Zn1 O21 Zn2 55.34(15) 2_745 . . . ?
O12 Zn1 O21 Zn2 -61.32(14) 3_755 . . . ?
Br1 Zn1 O21 Zn2 -173.51(5) . . . . ?
O11 Zn2 O21 C24 -5.8(3) . . . . ?
O11 Zn2 O21 C24 174.2(3) 3_755 . . . ?
O13 Zn2 O21 C24 -101.3(3) 4_565 . . . ?
O13 Zn2 O21 C24 78.7(3) 2_745 . . . ?
O21 Zn2 O21 C24 55.7(3) 3_755 . . . ?
O11 Zn2 O21 Zn1 -130.42(13) . . . . ?
O11 Zn2 O21 Zn1 49.58(13) 3_755 . . . ?
O13 Zn2 O21 Zn1 134.06(13) 4_565 . . . ?
O13 Zn2 O21 Zn1 -45.94(13) 2_745 . . . ?
O21 Zn2 O21 Zn1 -68.95(11) 3_755 . . . ?
C23 C21 C22 C23 -0.1(7) 3_765 . . . ?
C24 C21 C22 C23 -178.7(4) . . . . ?
C21 C22 C23 C21 0.1(8) . . . 3_765 ?
Zn1 O21 C24 O22 18.3(5) . . . . ?
Zn2 O21 C24 O22 -102.6(4) . . . . ?
Zn1 O21 C24 C21 -158.9(3) . . . . ?
Zn2 O21 C24 C21 80.2(4) . . . . ?
C22 C21 C24 O22 10.2(6) . . . . ?
C23 C21 C24 O22 -168.4(4) 3_765 . . . ?
C22 C21 C24 O21 -172.5(4) . . . . ?
C23 C21 C24 O21 8.9(6) 3_765 . . . ?
C2 N1 C1 N2 -0.2(10) . . . . ?
C2 N1 C1 C4 177.0(9) . . . . ?
C3 N2 C1 N1 0.1(9) . . . . ?
C3 N2 C1 C4 -176.7(10) . . . . ?
C1 N1 C2 C3 0.3(9) . . . . ?
N1 C2 C3 N2 -0.3(8) . . . . ?
N1 C2 C3 C5 -177.5(7) . . . . ?
C1 N2 C3 C2 0.1(9) . . . . ?
C1 N2 C3 C5 177.3(8) . . . . ?
C2 C3 C5 C6 99.2(11) . . . . ?
N2 C3 C5 C6 -77.5(12) . . . . ?
C3 C5 C6 C7 -15(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.236
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.095


####################################################################### 
# 
# 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_14
_audit_block_doi                 10.5517/cc1j5j8h
_database_code_depnum_ccdc_archive 'CCDC 1405486'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H12 Br2 O12 Zn3, 2(C8 H15 N2)'
_chemical_formula_sum            'C40 H42 Br2 N4 O12 Zn3'
_chemical_formula_weight         1126.71

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   13.1135(14)
_cell_length_b                   9.7503(6)
_cell_length_c                   18.2437(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.202(12)
_cell_angle_gamma                90.00
_cell_volume                     2189.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2176
_cell_measurement_theta_min      3.3470
_cell_measurement_theta_max      26.8700

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1132
_exptl_absorpt_coefficient_mu    3.521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88184
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Sphere (CrystalClear)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating-anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9730
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_sigmaI/netI    0.0691
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.75
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3837
_reflns_number_gt                2858
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Corp., 2002)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2002)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2002)'
_computing_structure_solution    'Siemens SHELXTLTM 5'
_computing_structure_refinement  'Siemens SHELXTLTM 5'
_computing_molecular_graphics    'Siemens SHELXTLTM 5'
_computing_publication_material  'Siemens SHELXTLTM 5'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0679P)²+3.8688P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3837
_refine_ls_number_parameters     277
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1494
_refine_ls_wR_factor_gt          0.1315
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.056
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.30779(5) 0.45106(6) 0.07260(3) 0.02646(17) Uani 1 1 d . . .
Zn2 Zn 0.5000 0.5000 0.0000 0.0232(2) Uani 1 2 d S . .
Br1 Br 0.16671(6) 0.34571(9) 0.10415(5) 0.0652(2) Uani 1 1 d . . .
O11 O 0.5287(4) 0.5809(4) 0.1103(2) 0.0437(11) Uani 1 1 d . . .
O12 O 0.3974(3) 0.5633(4) 0.1607(2) 0.0396(10) Uani 1 1 d . . .
O13 O 0.8698(3) 0.8804(4) 0.4468(2) 0.0415(11) Uani 1 1 d . . .
O14 O 0.7296(3) 0.9275(4) 0.4847(2) 0.0389(10) Uani 1 1 d . . .
C11 C 0.5621(5) 0.6692(6) 0.2343(3) 0.0320(13) Uani 1 1 d . . .
C12 C 0.5216(5) 0.7215(6) 0.2896(4) 0.0397(15) Uani 1 1 d . . .
H12A H 0.4483 0.7112 0.2826 0.048 Uiso 1 1 calc R . .
C13 C 0.5890(5) 0.7883(6) 0.3547(3) 0.0368(14) Uani 1 1 d . . .
H13A H 0.5603 0.8246 0.3906 0.044 Uiso 1 1 calc R . .
C14 C 0.6978(4) 0.8023(5) 0.3676(3) 0.0305(13) Uani 1 1 d . . .
C15 C 0.7396(5) 0.7496(7) 0.3133(4) 0.0477(17) Uani 1 1 d . . .
H15A H 0.8133 0.7585 0.3211 0.057 Uiso 1 1 calc R . .
C16 C 0.6710(5) 0.6833(7) 0.2472(4) 0.0487(17) Uani 1 1 d . . .
H16A H 0.6995 0.6478 0.2110 0.058 Uiso 1 1 calc R . .
C17 C 0.4903(5) 0.5992(5) 0.1634(3) 0.0285(13) Uani 1 1 d . . .
C18 C 0.7720(5) 0.8764(5) 0.4380(3) 0.0307(13) Uani 1 1 d . . .
O21 O 0.3963(3) 0.3400(3) 0.0249(2) 0.0294(9) Uani 1 1 d . . .
O22 O 0.4431(4) 0.2335(4) 0.1383(3) 0.0588(14) Uani 1 1 d . . .
C21 C 0.4726(5) 0.1170(5) 0.0332(4) 0.0353(14) Uani 1 1 d . . .
C22 C 0.5197(6) 0.0035(6) 0.0791(4) 0.0442(17) Uani 1 1 d . . .
H22A H 0.5325 0.0051 0.1325 0.053 Uiso 1 1 calc R . .
C23 C 0.5473(6) -0.1105(6) 0.0459(4) 0.0429(17) Uani 1 1 d . . .
H23A H 0.5800 -0.1846 0.0773 0.052 Uiso 1 1 calc R . .
C24 C 0.4383(5) 0.2366(5) 0.0710(4) 0.0389(15) Uani 1 1 d . . .
N1 N 0.2147(9) 0.8849(11) 0.1694(7) 0.129(3) Uani 1 1 d DU . .
N2 N 0.0957(10) 0.7522(12) 0.1582(7) 0.136(4) Uani 1 1 d DU . .
C1 C 0.1320(13) 0.8358(15) 0.1985(10) 0.149(5) Uani 1 1 d DU . .
H1A H 0.1143 0.8672 0.2408 0.178 Uiso 1 1 calc R . .
C2 C 0.1863(14) 0.8251(16) 0.0996(11) 0.190(5) Uani 1 1 d DU . .
H2A H 0.2137 0.8484 0.0606 0.228 Uiso 1 1 calc R . .
C3 C 0.1068(12) 0.7189(14) 0.0931(8) 0.133(4) Uani 1 1 d DU . .
H3A H 0.0755 0.6518 0.0559 0.159 Uiso 1 1 calc R . .
C4 C 0.2753(16) 1.0017(18) 0.1947(12) 0.209(7) Uani 1 1 d U . .
H4A H 0.3250 1.0125 0.1669 0.313 Uiso 1 1 calc R . .
H4B H 0.3153 0.9945 0.2496 0.313 Uiso 1 1 calc R . .
H4C H 0.2279 1.0798 0.1852 0.313 Uiso 1 1 calc R . .
C5 C 0.0042(15) 0.6870(19) 0.1655(12) 0.205(5) Uani 1 1 d DU . .
H5A H -0.0059 0.6122 0.1286 0.246 Uiso 1 1 calc R . .
H5B H 0.0358 0.6440 0.2163 0.246 Uiso 1 1 calc R . .
C6 C -0.1025(17) 0.708(2) 0.1627(14) 0.236(6) Uani 1 1 d DU . .
H6A H -0.1056 0.6917 0.2143 0.283 Uiso 1 1 calc R . .
H6B H -0.1489 0.6406 0.1277 0.283 Uiso 1 1 calc R . .
C7 C -0.146(2) 0.845(2) 0.1368(15) 0.274(7) Uani 1 1 d U . .
H7A H -0.1039 0.9041 0.1793 0.329 Uiso 1 1 calc R . .
H7B H -0.2181 0.8424 0.1400 0.329 Uiso 1 1 calc R . .
C8 C -0.1619(17) 0.940(2) 0.0572(13) 0.236(7) Uani 1 1 d U . .
H8A H -0.1899 1.0283 0.0634 0.354 Uiso 1 1 calc R . .
H8B H -0.2119 0.8949 0.0123 0.354 Uiso 1 1 calc R . .
H8C H -0.0930 0.9505 0.0502 0.354 Uiso 1 1 calc R . .


_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 O12 1.964(4) . ?
Zn1 O14 1.972(4) 4_575 ?
Zn1 O21 1.994(4) . ?
Zn1 Br1 2.3547(10) . ?
Zn2 O13 2.018(4) 2_645 ?
Zn2 O13 2.018(4) 4_575 ?
Zn2 O11 2.071(4) . ?
Zn2 O11 2.071(4) 3_665 ?
Zn2 O21 2.217(4) . ?
Zn2 O21 2.217(4) 3_665 ?
O11 C17 1.249(7) . ?
O12 C17 1.252(7) . ?
O13 C18 1.238(7) . ?
O13 Zn2 2.018(4) 2_655 ?
O14 C18 1.269(7) . ?
O14 Zn1 1.972(4) 4_676 ?
C11 C16 1.372(9) . ?
C11 C12 1.389(8) . ?
C11 C17 1.479(7) . ?
C12 C13 1.376(8) . ?
C12 H12A 0.9300 . ?
C13 C14 1.370(8) . ?
C13 H13A 0.9300 . ?
C14 C15 1.386(8) . ?
C14 C18 1.501(7) . ?
C15 C16 1.391(8) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
O21 C24 1.307(7) . ?
O22 C24 1.209(8) . ?
C21 C23 1.376(9) 3_655 ?
C21 C22 1.397(8) . ?
C21 C24 1.500(8) . ?
C22 C23 1.373(8) . ?
C22 H22A 0.9300 . ?
C23 C21 1.376(9) 3_655 ?
C23 H23A 0.9300 . ?
N1 C2 1.331(17) . ?
N1 C4 1.374(18) . ?
N1 C1 1.444(17) . ?
N2 C1 1.091(16) . ?
N2 C3 1.287(15) . ?
N2 C5 1.404(19) . ?
C1 H1A 0.9300 . ?
C2 C3 1.445(15) . ?
C2 H2A 0.9300 . ?
C3 H3A 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.397(16) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.47(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.67(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
O12 Zn1 O14 109.07(17) . 4_575 ?
O12 Zn1 O21 112.70(16) . . ?
O14 Zn1 O21 100.89(16) 4_575 . ?
O12 Zn1 Br1 109.99(13) . . ?
O14 Zn1 Br1 103.23(13) 4_575 . ?
O21 Zn1 Br1 119.64(11) . . ?
O13 Zn2 O13 180.0 2_645 4_575 ?
O13 Zn2 O11 85.03(18) 2_645 . ?
O13 Zn2 O11 94.97(18) 4_575 . ?
O13 Zn2 O11 94.97(18) 2_645 3_665 ?
O13 Zn2 O11 85.03(18) 4_575 3_665 ?
O11 Zn2 O11 180.0 . 3_665 ?
O13 Zn2 O21 88.38(15) 2_645 . ?
O13 Zn2 O21 91.62(15) 4_575 . ?
O11 Zn2 O21 89.29(15) . . ?
O11 Zn2 O21 90.71(15) 3_665 . ?
O13 Zn2 O21 91.62(15) 2_645 3_665 ?
O13 Zn2 O21 88.37(15) 4_575 3_665 ?
O11 Zn2 O21 90.71(15) . 3_665 ?
O11 Zn2 O21 89.29(15) 3_665 3_665 ?
O21 Zn2 O21 180.0(2) . 3_665 ?
C17 O11 Zn2 145.2(4) . . ?
C17 O12 Zn1 119.2(4) . . ?
C18 O13 Zn2 138.4(4) . 2_655 ?
C18 O14 Zn1 123.8(4) . 4_676 ?
C16 C11 C12 118.4(5) . . ?
C16 C11 C17 120.4(5) . . ?
C12 C11 C17 121.2(5) . . ?
C13 C12 C11 120.5(5) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C14 C13 C12 121.1(6) . . ?
C14 C13 H13A 119.5 . . ?
C12 C13 H13A 119.5 . . ?
C13 C14 C15 119.1(5) . . ?
C13 C14 C18 121.6(5) . . ?
C15 C14 C18 119.4(5) . . ?
C14 C15 C16 119.7(6) . . ?
C14 C15 H15A 120.1 . . ?
C16 C15 H15A 120.1 . . ?
C11 C16 C15 121.2(6) . . ?
C11 C16 H16A 119.4 . . ?
C15 C16 H16A 119.4 . . ?
O12 C17 O11 125.2(5) . . ?
O12 C17 C11 118.7(5) . . ?
O11 C17 C11 116.1(5) . . ?
O13 C18 O14 125.1(5) . . ?
O13 C18 C14 117.5(5) . . ?
O14 C18 C14 117.3(5) . . ?
C24 O21 Zn1 108.5(4) . . ?
C24 O21 Zn2 121.5(4) . . ?
Zn1 O21 Zn2 101.40(14) . . ?
C23 C21 C22 118.5(5) 3_655 . ?
C23 C21 C24 122.6(5) 3_655 . ?
C22 C21 C24 118.7(6) . . ?
C23 C22 C21 120.4(6) . . ?
C23 C22 H22A 119.8 . . ?
C21 C22 H22A 119.8 . . ?
C22 C23 C21 121.1(6) . 3_655 ?
C22 C23 H23A 119.4 . . ?
C21 C23 H23A 119.4 3_655 . ?
O22 C24 O21 122.4(5) . . ?
O22 C24 C21 122.0(5) . . ?
O21 C24 C21 115.5(5) . . ?
C2 N1 C4 128.5(16) . . ?
C2 N1 C1 102.1(13) . . ?
C4 N1 C1 124.9(15) . . ?
C1 N2 C3 130.5(17) . . ?
C1 N2 C5 117.5(17) . . ?
C3 N2 C5 110.3(14) . . ?
N2 C1 N1 102.0(16) . . ?
N2 C1 H1A 129.0 . . ?
N1 C1 H1A 129.0 . . ?
N1 C2 C3 110.4(16) . . ?
N1 C2 H2A 124.8 . . ?
C3 C2 H2A 124.8 . . ?
N2 C3 C2 92.9(14) . . ?
N2 C3 H3A 133.5 . . ?
C2 C3 H3A 133.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N2 143.9(19) . . ?
C6 C5 H5A 100.9 . . ?
N2 C5 H5A 100.9 . . ?
C6 C5 H5B 100.9 . . ?
N2 C5 H5B 100.9 . . ?
H5A C5 H5B 104.4 . . ?
C5 C6 C7 115(2) . . ?
C5 C6 H6A 108.6 . . ?
C7 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
C7 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C6 C7 C8 135(2) . . ?
C6 C7 H7A 103.5 . . ?
C8 C7 H7A 103.5 . . ?
C6 C7 H7B 103.5 . . ?
C8 C7 H7B 103.5 . . ?
H7A C7 H7B 105.3 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
O13 Zn2 O11 C17 -119.7(7) 2_645 . . . ?
O13 Zn2 O11 C17 60.3(7) 4_575 . . . ?
O11 Zn2 O11 C17 -165(65) 3_665 . . . ?
O21 Zn2 O11 C17 -31.3(7) . . . . ?
O21 Zn2 O11 C17 148.7(7) 3_665 . . . ?
O14 Zn1 O12 C17 -85.2(4) 4_575 . . . ?
O21 Zn1 O12 C17 26.0(4) . . . . ?
Br1 Zn1 O12 C17 162.3(4) . . . . ?
C16 C11 C12 C13 1.4(9) . . . . ?
C17 C11 C12 C13 -178.9(5) . . . . ?
C11 C12 C13 C14 -1.5(10) . . . . ?
C12 C13 C14 C15 0.9(9) . . . . ?
C12 C13 C14 C18 179.3(5) . . . . ?
C13 C14 C15 C16 -0.2(10) . . . . ?
C18 C14 C15 C16 -178.7(6) . . . . ?
C12 C11 C16 C15 -0.8(10) . . . . ?
C17 C11 C16 C15 179.6(6) . . . . ?
C14 C15 C16 C11 0.2(10) . . . . ?
Zn1 O12 C17 O11 7.3(8) . . . . ?
Zn1 O12 C17 C11 -172.7(4) . . . . ?
Zn2 O11 C17 O12 -1.1(11) . . . . ?
Zn2 O11 C17 C11 178.9(5) . . . . ?
C16 C11 C17 O12 165.6(6) . . . . ?
C12 C11 C17 O12 -14.0(8) . . . . ?
C16 C11 C17 O11 -14.4(8) . . . . ?
C12 C11 C17 O11 166.0(5) . . . . ?
Zn2 O13 C18 O14 -26.6(10) 2_655 . . . ?
Zn2 O13 C18 C14 155.1(4) 2_655 . . . ?
Zn1 O14 C18 O13 10.1(8) 4_676 . . . ?
Zn1 O14 C18 C14 -171.6(3) 4_676 . . . ?
C13 C14 C18 O13 177.5(6) . . . . ?
C15 C14 C18 O13 -4.1(8) . . . . ?
C13 C14 C18 O14 -1.0(8) . . . . ?
C15 C14 C18 O14 177.5(5) . . . . ?
O12 Zn1 O21 C24 75.5(4) . . . . ?
O14 Zn1 O21 C24 -168.4(4) 4_575 . . . ?
Br1 Zn1 O21 C24 -56.2(4) . . . . ?
O12 Zn1 O21 Zn2 -53.57(19) . . . . ?
O14 Zn1 O21 Zn2 62.61(17) 4_575 . . . ?
Br1 Zn1 O21 Zn2 174.80(6) . . . . ?
O13 Zn2 O21 C24 10.0(4) 2_645 . . . ?
O13 Zn2 O21 C24 -170.0(4) 4_575 . . . ?
O11 Zn2 O21 C24 -75.0(4) . . . . ?
O11 Zn2 O21 C24 105.0(4) 3_665 . . . ?
O21 Zn2 O21 C24 -144(82) 3_665 . . . ?
O13 Zn2 O21 Zn1 130.24(17) 2_645 . . . ?
O13 Zn2 O21 Zn1 -49.76(17) 4_575 . . . ?
O11 Zn2 O21 Zn1 45.19(17) . . . . ?
O11 Zn2 O21 Zn1 -134.81(17) 3_665 . . . ?
O21 Zn2 O21 Zn1 -23(81) 3_665 . . . ?
C23 C21 C22 C23 1.2(11) 3_655 . . . ?
C24 C21 C22 C23 176.9(6) . . . . ?
C21 C22 C23 C21 -1.3(11) . . . 3_655 ?
Zn1 O21 C24 O22 -16.7(7) . . . . ?
Zn2 O21 C24 O22 100.0(7) . . . . ?
Zn1 O21 C24 C21 158.8(4) . . . . ?
Zn2 O21 C24 C21 -84.5(5) . . . . ?
C23 C21 C24 O22 170.0(7) 3_655 . . . ?
C22 C21 C24 O22 -5.5(9) . . . . ?
C23 C21 C24 O21 -5.5(9) 3_655 . . . ?
C22 C21 C24 O21 179.0(6) . . . . ?
C3 N2 C1 N1 -12(2) . . . . ?
C5 N2 C1 N1 -174.7(12) . . . . ?
C2 N1 C1 N2 13.9(16) . . . . ?
C4 N1 C1 N2 171.6(14) . . . . ?
C4 N1 C2 C3 -169.8(15) . . . . ?
C1 N1 C2 C3 -13.3(16) . . . . ?
C1 N2 C3 C2 3(2) . . . . ?
C5 N2 C3 C2 167.4(13) . . . . ?
N1 C2 C3 N2 7.8(16) . . . . ?
C1 N2 C5 C6 60(4) . . . . ?
C3 N2 C5 C6 -106(3) . . . . ?
N2 C5 C6 C7 7(5) . . . . ?
C5 C6 C7 C8 57(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.112
_refine_diff_density_min         -0.857
_refine_diff_density_rms         0.119

####################################################################### 
# 
# 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_15
_audit_block_doi                 10.5517/cc1j5j9j
_database_code_depnum_ccdc_archive 'CCDC 1405487'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 H4 O6 Zn'
_chemical_formula_sum            'C2 H4 O6 Zn'
_chemical_formula_weight         189.42

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'


loop_
_symmetry_equiv_pos_as_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                   11.786(3)
_cell_length_b                   5.3955(5)
_cell_length_c                   9.712(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 126.22(3)
_cell_angle_gamma                90.00
_cell_volume                     498.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    391
_cell_measurement_theta_min      5.6270
_cell_measurement_theta_max      27.7730

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    4.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.47040
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Sphere (CrystalClear)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating-anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 16.0356
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            832
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.29
_diffrn_reflns_theta_max         25.00
_reflns_number_total             439
_reflns_number_gt                413
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Corp., 2002)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2002)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2002)'
_computing_structure_solution    'Siemens SHELXTLTM 5'
_computing_structure_refinement  'Siemens SHELXTLTM 5'
_computing_molecular_graphics    'Siemens SHELXTLTM 5'
_computing_publication_material  'Siemens SHELXTLTM 5'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0547P)²+2.9298P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         439
_refine_ls_number_parameters     50
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.1071
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.082
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.0000 0.07254(15) 0.2500 0.0221(4) Uani 1 2 d S . .
C1 C -0.0513(5) -0.4242(9) 0.1493(6) 0.0174(12) Uani 1 1 d . . .
O1 O -0.0868(4) -0.2200(7) 0.0787(4) 0.0214(9) Uani 1 1 d . . .
O2 O -0.0869(4) -0.6322(7) 0.0781(4) 0.0225(9) Uani 1 1 d . . .
O1W O 0.1759(4) 0.0635(7) 0.2430(5) 0.0267(10) Uani 1 1 d D . .
H1WB H 0.163(6) 0.144(11) 0.148(5) 0.038(18) Uiso 1 1 d D . .
H1WA H 0.259(5) 0.121(14) 0.345(4) 0.07(3) Uiso 1 1 d 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 O1 2.072(4) . ?
Zn1 O1 2.072(4) 2 ?
Zn1 O2 2.086(4) 2_565 ?
Zn1 O2 2.086(4) 1_565 ?
Zn1 O1W 2.115(4) 2 ?
Zn1 O1W 2.115(4) . ?
C1 O1 1.233(6) . ?
C1 O2 1.253(6) . ?
C1 C1 1.579(10) 2 ?
O2 Zn1 2.086(4) 1_545 ?
O1W H1WB 0.947(10) . ?
O1W H1WA 0.946(11) . ?

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
O1 Zn1 O1 80.76(19) . 2 ?
O1 Zn1 O2 179.83(17) . 2_565 ?
O1 Zn1 O2 99.39(14) 2 2_565 ?
O1 Zn1 O2 99.39(14) . 1_565 ?
O1 Zn1 O2 179.83(17) 2 1_565 ?
O2 Zn1 O2 80.5(2) 2_565 1_565 ?
O1 Zn1 O1W 88.84(15) . 2 ?
O1 Zn1 O1W 89.15(15) 2 2 ?
O2 Zn1 O1W 91.09(15) 2_565 2 ?
O2 Zn1 O1W 90.93(16) 1_565 2 ?
O1 Zn1 O1W 89.15(15) . . ?
O1 Zn1 O1W 88.84(15) 2 . ?
O2 Zn1 O1W 90.93(16) 2_565 . ?
O2 Zn1 O1W 91.09(15) 1_565 . ?
O1W Zn1 O1W 177.4(2) 2 . ?
O1 C1 O2 126.9(4) . . ?
O1 C1 C1 116.7(3) . 2 ?
O2 C1 C1 116.4(3) . 2 ?
C1 O1 Zn1 113.0(3) . . ?
C1 O2 Zn1 113.3(3) . 1_545 ?
Zn1 O1W H1WB 115(4) . . ?
Zn1 O1W H1WA 113(5) . . ?
H1WB O1W H1WA 109.8(17) . . ?

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
O2 C1 O1 Zn1 -179.7(4) . . . . ?
C1 C1 O1 Zn1 -0.3(7) 2 . . . ?
O1 Zn1 O1 C1 0.1(3) 2 . . . ?
O2 Zn1 O1 C1 -155(100) 2_565 . . . ?
O2 Zn1 O1 C1 -179.9(4) 1_565 . . . ?
O1W Zn1 O1 C1 -89.2(4) 2 . . . ?
O1W Zn1 O1 C1 89.1(4) . . . . ?
O1 C1 O2 Zn1 179.8(4) . . . 1_545 ?
C1 C1 O2 Zn1 0.5(7) 2 . . 1_545 ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.190
_refine_diff_density_min         -0.958
_refine_diff_density_rms         0.143


####################################################################### 
# 
# 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_14
_audit_block_doi                 10.5517/cc1j5jbk
_database_code_depnum_ccdc_archive 'CCDC 1405488'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H12 I2 O12 Zn3, 2(C6 H11 N2)'
_chemical_formula_sum            'C36 H34 I2 N4 O12 Zn3'
_chemical_formula_weight         1164.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   13.2282(8)
_cell_length_b                   9.3686(3)
_cell_length_c                   18.6590(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.270(5)
_cell_angle_gamma                90.00
_cell_volume                     2169.20(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1140
_exptl_absorpt_coefficient_mu    3.130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_T_max  0.855
_exptl_absorpt_process_details   'Sphere (CrystalClear)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating-anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9024
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.77
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3806
_reflns_number_gt                2841
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Corp., 2002)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2002)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2002)'
_computing_structure_solution    'Siemens SHELXTLTM 5'
_computing_structure_refinement  'Siemens SHELXTLTM 5'
_computing_molecular_graphics    'Siemens SHELXTLTM 5'
_computing_publication_material  'Siemens SHELXTLTM 5'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0537P)²+3.9071P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3806
_refine_ls_number_parameters     259
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1210
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.022
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.80504(5) 0.96751(7) 0.06861(3) 0.02244(19) Uani 1 1 d . . .
Zn2 Zn 1.0000 1.0000 0.0000 0.0203(2) Uani 1 2 d S . .
I1 I 0.64947(5) 0.83850(7) 0.09152(4) 0.0696(2) Uani 1 1 d . . .
O11 O 0.8954(3) 1.0785(4) 0.1553(2) 0.0354(10) Uani 1 1 d . . .
O12 O 1.0261(4) 1.0925(4) 0.1054(2) 0.0405(11) Uani 1 1 d . . .
O13 O 1.2352(3) 1.4019(5) 0.4832(2) 0.0389(11) Uani 1 1 d . . .
O14 O 1.3731(3) 1.3751(5) 0.4426(2) 0.0393(11) Uani 1 1 d . . .
C11 C 1.0652(5) 1.1718(6) 0.2310(3) 0.0312(14) Uani 1 1 d . . .
C12 C 1.0273(5) 1.2112(8) 0.2882(4) 0.0442(18) Uani 1 1 d . . .
H12A H 0.9553 1.1963 0.2821 0.053 Uiso 1 1 calc R . .
C13 C 1.0960(5) 1.2731(8) 0.3550(4) 0.0469(19) Uani 1 1 d . . .
H13A H 1.0695 1.3025 0.3927 0.056 Uiso 1 1 calc R . .
C14 C 1.2037(5) 1.2909(6) 0.3652(3) 0.0306(14) Uani 1 1 d . . .
C15 C 1.2406(5) 1.2487(7) 0.3076(3) 0.0395(16) Uani 1 1 d . . .
H15A H 1.3130 1.2602 0.3138 0.047 Uiso 1 1 calc R . .
C16 C 1.1720(5) 1.1903(8) 0.2416(4) 0.0427(17) Uani 1 1 d . . .
H16A H 1.1982 1.1627 0.2034 0.051 Uiso 1 1 calc R . .
C17 C 0.9900(5) 1.1089(6) 0.1580(3) 0.0285(13) Uani 1 1 d . . .
C18 C 1.2768(5) 1.3615(6) 0.4360(3) 0.0279(13) Uani 1 1 d . . .
O21 O 0.8935(3) 0.8469(4) 0.0269(2) 0.0271(9) Uani 1 1 d . . .
O22 O 0.9413(5) 0.7346(5) 0.1384(3) 0.0543(14) Uani 1 1 d . . .
C21 C 0.9686(5) 0.6147(6) 0.0334(3) 0.0299(14) Uani 1 1 d . . .
C22 C 1.0335(6) 0.5092(6) 0.0785(4) 0.0376(16) Uani 1 1 d . . .
H22A H 1.0564 0.5161 0.1315 0.045 Uiso 1 1 calc R . .
C23 C 0.9358(5) 0.6059(6) -0.0449(4) 0.0361(15) Uani 1 1 d . . .
H23A H 0.8930 0.6774 -0.0750 0.043 Uiso 1 1 calc R . .
C24 C 0.9348(5) 0.7380(6) 0.0720(4) 0.0301(14) Uani 1 1 d . . .
N1 N 0.6893(8) 1.3659(10) 0.1198(7) 0.090(3) Uani 1 1 d . . .
N2 N 0.5693(7) 1.2616(9) 0.1512(4) 0.083(2) Uani 1 1 d . . .
C1 C 0.6136(10) 1.2729(12) 0.0989(6) 0.084(3) Uani 1 1 d . . .
H1A H 0.5934 1.2215 0.0535 0.101 Uiso 1 1 calc R . .
C2 C 0.6988(13) 1.4135(15) 0.1849(8) 0.124(5) Uani 1 1 d . . .
H2A H 0.7502 1.4783 0.2136 0.149 Uiso 1 1 calc R . .
C3 C 0.6216(12) 1.3537(16) 0.2051(7) 0.117(5) Uani 1 1 d . . .
H3A H 0.6068 1.3732 0.2494 0.140 Uiso 1 1 calc R . .
C4 C 0.7586(14) 1.4145(14) 0.0783(10) 0.159(7) Uani 1 1 d . . .
H4A H 0.8069 1.4867 0.1075 0.239 Uiso 1 1 calc R . .
H4B H 0.7150 1.4533 0.0298 0.239 Uiso 1 1 calc R . .
H4C H 0.7996 1.3353 0.0703 0.239 Uiso 1 1 calc R . .
C5 C 0.4766(13) 1.1670(16) 0.1485(10) 0.146(6) Uani 1 1 d . . .
H5A H 0.4619 1.1009 0.1061 0.175 Uiso 1 1 calc R . .
H5B H 0.4952 1.1118 0.1953 0.175 Uiso 1 1 calc R . .
C6 C 0.3859(15) 1.248(2) 0.1400(11) 0.194(8) Uani 1 1 d U . .
H6A H 0.3276 1.1865 0.1393 0.291 Uiso 1 1 calc R . .
H6B H 0.3663 1.3002 0.0928 0.291 Uiso 1 1 calc R . .
H6C H 0.4008 1.3138 0.1818 0.291 Uiso 1 1 calc R . .


_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 O11 1.947(4) . ?
Zn1 O13 1.968(4) 4_585 ?
Zn1 O21 1.970(4) . ?
Zn1 I1 2.5472(8) . ?
Zn2 O14 2.022(4) 2_745 ?
Zn2 O14 2.022(4) 4_585 ?
Zn2 O12 2.065(4) . ?
Zn2 O12 2.065(4) 3_775 ?
Zn2 O21 2.187(4) 3_775 ?
Zn2 O21 2.187(4) . ?
O11 C17 1.266(7) . ?
O12 C17 1.242(7) . ?
O13 C18 1.248(7) . ?
O13 Zn1 1.968(4) 4_686 ?
O14 C18 1.243(7) . ?
O14 Zn2 2.022(4) 2_755 ?
C11 C16 1.368(9) . ?
C11 C12 1.377(8) . ?
C11 C17 1.501(8) . ?
C12 C13 1.389(8) . ?
C12 H12A 0.9300 . ?
C13 C14 1.380(9) . ?
C13 H13A 0.9300 . ?
C14 C15 1.384(8) . ?
C14 C18 1.494(8) . ?
C15 C16 1.365(8) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
O21 C24 1.315(7) . ?
O22 C24 1.212(7) . ?
C21 C23 1.374(8) . ?
C21 C22 1.387(8) . ?
C21 C24 1.509(8) . ?
C22 C23 1.378(8) 3_765 ?
C22 H22A 0.9300 . ?
C23 C22 1.378(8) 3_765 ?
C23 H23A 0.9300 . ?
N1 C2 1.260(14) . ?
N1 C1 1.282(13) . ?
N1 C4 1.463(15) . ?
N2 C1 1.305(12) . ?
N2 C3 1.325(13) . ?
N2 C5 1.499(15) . ?
C1 H1A 0.9300 . ?
C2 C3 1.328(17) . ?
C2 H2A 0.9300 . ?
C3 H3A 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.38(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 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
O11 Zn1 O13 108.79(19) . 4_585 ?
O11 Zn1 O21 110.91(17) . . ?
O13 Zn1 O21 102.29(17) 4_585 . ?
O11 Zn1 I1 114.42(13) . . ?
O13 Zn1 I1 104.54(13) 4_585 . ?
O21 Zn1 I1 114.78(11) . . ?
O14 Zn2 O14 180.0 2_745 4_585 ?
O14 Zn2 O12 84.52(19) 2_745 . ?
O14 Zn2 O12 95.48(19) 4_585 . ?
O14 Zn2 O12 95.48(19) 2_745 3_775 ?
O14 Zn2 O12 84.52(19) 4_585 3_775 ?
O12 Zn2 O12 180.000(1) . 3_775 ?
O14 Zn2 O21 91.08(16) 2_745 3_775 ?
O14 Zn2 O21 88.92(15) 4_585 3_775 ?
O12 Zn2 O21 92.00(15) . 3_775 ?
O12 Zn2 O21 88.00(15) 3_775 3_775 ?
O14 Zn2 O21 88.92(15) 2_745 . ?
O14 Zn2 O21 91.08(16) 4_585 . ?
O12 Zn2 O21 88.00(15) . . ?
O12 Zn2 O21 92.00(15) 3_775 . ?
O21 Zn2 O21 180.00(19) 3_775 . ?
C17 O11 Zn1 117.8(4) . . ?
C17 O12 Zn2 145.3(4) . . ?
C18 O13 Zn1 124.2(4) . 4_686 ?
C18 O14 Zn2 138.2(4) . 2_755 ?
C16 C11 C12 119.2(6) . . ?
C16 C11 C17 120.5(5) . . ?
C12 C11 C17 120.2(6) . . ?
C11 C12 C13 120.5(6) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C14 C13 C12 119.8(6) . . ?
C14 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?
C13 C14 C15 118.8(5) . . ?
C13 C14 C18 119.8(5) . . ?
C15 C14 C18 121.3(6) . . ?
C16 C15 C14 120.8(6) . . ?
C16 C15 H15A 119.6 . . ?
C14 C15 H15A 119.6 . . ?
C11 C16 C15 120.8(6) . . ?
C11 C16 H16A 119.6 . . ?
C15 C16 H16A 119.6 . . ?
O12 C17 O11 125.9(5) . . ?
O12 C17 C11 116.8(6) . . ?
O11 C17 C11 117.4(5) . . ?
O14 C18 O13 125.9(5) . . ?
O14 C18 C14 117.4(5) . . ?
O13 C18 C14 116.7(5) . . ?
C24 O21 Zn1 111.4(4) . . ?
C24 O21 Zn2 119.9(4) . . ?
Zn1 O21 Zn2 103.45(15) . . ?
C23 C21 C22 120.3(5) . . ?
C23 C21 C24 121.1(5) . . ?
C22 C21 C24 118.7(5) . . ?
C23 C22 C21 119.9(6) 3_765 . ?
C23 C22 H22A 120.0 3_765 . ?
C21 C22 H22A 120.0 . . ?
C21 C23 C22 119.8(6) . 3_765 ?
C21 C23 H23A 120.1 . . ?
C22 C23 H23A 120.1 3_765 . ?
O22 C24 O21 122.7(5) . . ?
O22 C24 C21 122.6(5) . . ?
O21 C24 C21 114.6(5) . . ?
C2 N1 C1 109.9(11) . . ?
C2 N1 C4 122.0(13) . . ?
C1 N1 C4 128.1(12) . . ?
C1 N2 C3 105.3(11) . . ?
C1 N2 C5 126.7(11) . . ?
C3 N2 C5 128.1(12) . . ?
N1 C1 N2 109.5(9) . . ?
N1 C1 H1A 125.2 . . ?
N2 C1 H1A 125.2 . . ?
N1 C2 C3 107.2(12) . . ?
N1 C2 H2A 126.4 . . ?
C3 C2 H2A 126.4 . . ?
N2 C3 C2 108.1(11) . . ?
N2 C3 H3A 126.0 . . ?
C2 C3 H3A 126.0 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N2 110.2(14) . . ?
C6 C5 H5A 109.6 . . ?
N2 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
N2 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 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
O13 Zn1 O11 C17 -84.7(4) 4_585 . . . ?
O21 Zn1 O11 C17 27.1(5) . . . . ?
I1 Zn1 O11 C17 158.8(4) . . . . ?
O14 Zn2 O12 C17 -111.4(8) 2_745 . . . ?
O14 Zn2 O12 C17 68.6(8) 4_585 . . . ?
O12 Zn2 O12 C17 37(100) 3_775 . . . ?
O21 Zn2 O12 C17 157.7(7) 3_775 . . . ?
O21 Zn2 O12 C17 -22.3(7) . . . . ?
C16 C11 C12 C13 2.0(11) . . . . ?
C17 C11 C12 C13 -178.2(6) . . . . ?
C11 C12 C13 C14 -2.2(12) . . . . ?
C12 C13 C14 C15 1.2(11) . . . . ?
C12 C13 C14 C18 178.1(6) . . . . ?
C13 C14 C15 C16 0.0(10) . . . . ?
C18 C14 C15 C16 -176.9(6) . . . . ?
C12 C11 C16 C15 -0.8(11) . . . . ?
C17 C11 C16 C15 179.4(6) . . . . ?
C14 C15 C16 C11 -0.1(11) . . . . ?
Zn2 O12 C17 O11 -12.6(12) . . . . ?
Zn2 O12 C17 C11 168.1(5) . . . . ?
Zn1 O11 C17 O12 11.1(8) . . . . ?
Zn1 O11 C17 C11 -169.7(4) . . . . ?
C16 C11 C17 O12 -9.0(9) . . . . ?
C12 C11 C17 O12 171.2(6) . . . . ?
C16 C11 C17 O11 171.6(6) . . . . ?
C12 C11 C17 O11 -8.1(9) . . . . ?
Zn2 O14 C18 O13 -22.6(10) 2_755 . . . ?
Zn2 O14 C18 C14 157.3(5) 2_755 . . . ?
Zn1 O13 C18 O14 13.7(9) 4_686 . . . ?
Zn1 O13 C18 C14 -166.2(4) 4_686 . . . ?
C13 C14 C18 O14 180.0(6) . . . . ?
C15 C14 C18 O14 -3.2(9) . . . . ?
C13 C14 C18 O13 -0.2(9) . . . . ?
C15 C14 C18 O13 176.7(6) . . . . ?
O11 Zn1 O21 C24 73.6(4) . . . . ?
O13 Zn1 O21 C24 -170.6(4) 4_585 . . . ?
I1 Zn1 O21 C24 -58.0(4) . . . . ?
O11 Zn1 O21 Zn2 -56.5(2) . . . . ?
O13 Zn1 O21 Zn2 59.4(2) 4_585 . . . ?
I1 Zn1 O21 Zn2 171.93(8) . . . . ?
O14 Zn2 O21 C24 5.3(4) 2_745 . . . ?
O14 Zn2 O21 C24 -174.7(4) 4_585 . . . ?
O12 Zn2 O21 C24 -79.3(4) . . . . ?
O12 Zn2 O21 C24 100.7(4) 3_775 . . . ?
O21 Zn2 O21 C24 165(44) 3_775 . . . ?
O14 Zn2 O21 Zn1 129.96(19) 2_745 . . . ?
O14 Zn2 O21 Zn1 -50.04(19) 4_585 . . . ?
O12 Zn2 O21 Zn1 45.41(19) . . . . ?
O12 Zn2 O21 Zn1 -134.59(19) 3_775 . . . ?
O21 Zn2 O21 Zn1 -70(14) 3_775 . . . ?
C23 C21 C22 C23 -0.8(11) . . . 3_765 ?
C24 C21 C22 C23 179.0(6) . . . 3_765 ?
C22 C21 C23 C22 0.8(11) . . . 3_765 ?
C24 C21 C23 C22 -178.9(6) . . . 3_765 ?
Zn1 O21 C24 O22 -18.2(7) . . . . ?
Zn2 O21 C24 O22 102.6(6) . . . . ?
Zn1 O21 C24 C21 159.0(4) . . . . ?
Zn2 O21 C24 C21 -80.1(5) . . . . ?
C23 C21 C24 O22 163.2(6) . . . . ?
C22 C21 C24 O22 -16.6(9) . . . . ?
C23 C21 C24 O21 -14.0(8) . . . . ?
C22 C21 C24 O21 166.2(5) . . . . ?
C2 N1 C1 N2 1.9(15) . . . . ?
C4 N1 C1 N2 -178.7(11) . . . . ?
C3 N2 C1 N1 0.5(14) . . . . ?
C5 N2 C1 N1 178.8(11) . . . . ?
C1 N1 C2 C3 -3.4(17) . . . . ?
C4 N1 C2 C3 177.1(13) . . . . ?
C1 N2 C3 C2 -2.5(16) . . . . ?
C5 N2 C3 C2 179.2(13) . . . . ?
N1 C2 C3 N2 3.7(18) . . . . ?
C1 N2 C5 C6 -110.2(17) . . . . ?
C3 N2 C5 C6 68(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.752
_refine_diff_density_min         -1.287
_refine_diff_density_rms         0.118

####################################################################### 
# 
# 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_a
_audit_block_doi                 10.5517/cc1j5jcl
_database_code_depnum_ccdc_archive 'CCDC 1405489'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H26 I2 O12 Zn3, 2(C4 H6 N2)'
_chemical_formula_sum            'C38 H38 I2 N4 O12 Zn3'
_chemical_formula_weight         1192.63

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   13.3440(9)
_cell_length_b                   9.4033(6)
_cell_length_c                   18.5203(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.126(7)
_cell_angle_gamma                90.00
_cell_volume                     2182.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1229
_cell_measurement_theta_min      3.9330
_cell_measurement_theta_max      26.4770

_exptl_crystal_description       Prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1172
_exptl_absorpt_coefficient_mu    3.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98152
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Sphere (CrystalClear)'

_exptl_special_details           
;                                                               
 ?                                                              
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating-anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8610
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_sigmaI/netI    0.1199
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.74
_diffrn_reflns_theta_max         25.03
_reflns_number_total             3832
_reflns_number_gt                2334
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Corp., 2002)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2002)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2002)'
_computing_structure_solution    'Siemens SHELXTLTM 5'
_computing_structure_refinement  'Siemens SHELXTLTM 5'
_computing_molecular_graphics    'Siemens SHELXTLTM 5'
_computing_publication_material  'Siemens SHELXTLTM 5'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1538P)²+5.5403P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3832
_refine_ls_number_parameters     268
_refine_ls_number_restraints     126
_refine_ls_R_factor_all          0.1595
_refine_ls_R_factor_gt           0.1043
_refine_ls_wR_factor_ref         0.3202
_refine_ls_wR_factor_gt          0.2723
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_restrained_S_all      1.201
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.0000 0.0000 0.0000 0.0193(3) Uani 1 2 d S . .
Zn2 Zn 0.19552(6) 0.03350(8) -0.06791(4) 0.0224(2) Uani 1 1 d . . .
I1 I 0.33893(5) 0.14803(9) -0.10953(4) 0.0758(2) Uani 1 1 d . . .
C11 C -0.0654(4) -0.1846(8) -0.2264(3) 0.050(2) Uani 1 1 d D . .
C12 C -0.1584(5) -0.2265(11) -0.2310(5) 0.071(3) Uani 1 1 d DU . .
H12A H -0.1753 -0.2295 -0.1864 0.085 Uiso 1 1 calc R . .
C16 C -0.0264(5) -0.2188(8) -0.2860(3) 0.035(2) Uani 1 1 d D . .
H16A H 0.0444 -0.2017 -0.2809 0.042 Uiso 1 1 calc R . .
C17 C 0.0127(4) -0.1188(8) -0.1526(3) 0.037(2) Uani 1 1 d D . .
O11 O 0.1001(3) -0.0784(5) -0.1541(2) 0.0360(15) Uani 1 1 d D . .
O12 O -0.0162(5) -0.1132(7) -0.0961(3) 0.0737(19) Uani 1 1 d DU . .
C21 C -0.0589(6) -0.3829(8) 0.0016(5) 0.0793(19) Uani 1 1 d DU . .
C22 C 0.0266(8) -0.3967(12) 0.0543(5) 0.089(3) Uani 1 1 d DU . .
H22A H 0.0487 -0.3280 0.0926 0.107 Uiso 1 1 calc R . .
C23 C -0.0886(11) -0.4886(11) -0.0567(6) 0.114(3) Uani 1 1 d DU . .
H23A H -0.1524 -0.4786 -0.0977 0.137 Uiso 1 1 calc R . .
C24 C -0.1376(6) -0.2602(8) -0.0023(5) 0.0746(17) Uani 1 1 d DU . .
O21 O -0.2339(6) -0.2695(10) -0.0405(5) 0.109(3) Uani 1 1 d DU . .
O22 O -0.0989(4) -0.1523(5) 0.0342(2) 0.0359(12) Uani 1 1 d DU . .
C13 C -0.2359(8) -0.2682(12) -0.3004(5) 0.074(3) Uani 1 1 d U . .
H13A H -0.3079 -0.2716 -0.3061 0.088 Uiso 1 1 calc R . .
C14 C -0.2006(6) -0.3041(9) -0.3600(4) 0.0379(16) Uani 1 1 d U . .
C15 C -0.0956(5) -0.2777(8) -0.3513(4) 0.033(2) Uani 1 1 d . . .
H15A H -0.0713 -0.3008 -0.3912 0.040 Uiso 1 1 calc R . .
C18 C -0.2735(5) -0.3772(8) -0.4300(4) 0.039(2) Uani 1 1 d . . .
O13 O -0.3674(4) -0.3985(6) -0.4356(3) 0.0582(17) Uani 1 1 d U . .
O14 O -0.2367(4) -0.4061(6) -0.4815(3) 0.0391(15) Uani 1 1 d . . .
N1 N 0.6741(7) 0.3689(10) 0.1104(5) 0.080(3) Uani 1 1 d U . .
N2 N 0.5587(12) 0.2680(17) 0.1422(8) 0.159(3) Uani 1 1 d U . .
C1 C 0.5994(13) 0.2791(14) 0.0820(7) 0.120(6) Uani 1 1 d . . .
H1A H 0.5779 0.2336 0.0345 0.144 Uiso 1 1 calc R . .
C2 C 0.6978(13) 0.4045(18) 0.1728(9) 0.126(2) Uani 1 1 d U . .
H2A H 0.7591 0.4529 0.2020 0.152 Uiso 1 1 calc R . .
C3 C 0.6246(13) 0.3648(18) 0.1924(9) 0.135(4) Uani 1 1 d U . .
H3A H 0.6139 0.3963 0.2369 0.161 Uiso 1 1 calc R . .
C4 C 0.7421(12) 0.4002(18) 0.0684(9) 0.139(4) Uani 1 1 d U . .
H4A H 0.7971 0.4643 0.0976 0.209 Uiso 1 1 calc R . .
H4B H 0.7014 0.4437 0.0204 0.209 Uiso 1 1 calc R . .
H4C H 0.7738 0.3139 0.0588 0.209 Uiso 1 1 calc R . .
C5 C 0.4613(15) 0.140(2) 0.1352(11) 0.169(2) Uani 1 1 d U . .
H5A H 0.4036 0.1454 0.0861 0.203 Uiso 1 1 calc R . .
H5B H 0.4910 0.0452 0.1427 0.203 Uiso 1 1 calc R . .
C6 C 0.4264(16) 0.183(2) 0.1978(12) 0.193(4) Uani 1 1 d U . .
H6A H 0.3671 0.1286 0.2026 0.232 Uiso 1 1 calc R . .
H6B H 0.4830 0.1959 0.2470 0.232 Uiso 1 1 calc R . .
C7 C 0.393(2) 0.327(3) 0.1441(16) 0.263(8) Uani 1 1 d U . .
H7A H 0.3869 0.4055 0.1752 0.395 Uiso 1 1 calc R . .
H7B H 0.3255 0.3112 0.1038 0.395 Uiso 1 1 calc R . .
H7C H 0.4465 0.3466 0.1218 0.395 Uiso 1 1 calc R . .


_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 O13 2.002(5) 2_454 ?
Zn1 O13 2.002(5) 4_656 ?
Zn1 O12 2.021(6) . ?
Zn1 O12 2.021(6) 3 ?
Zn1 O22 2.183(5) 3 ?
Zn1 O22 2.183(5) . ?
Zn2 O14 1.954(5) 4_656 ?
Zn2 O22 1.964(5) 3 ?
Zn2 O11 1.969(4) . ?
Zn2 I1 2.5361(11) . ?
C11 C12 1.276(9) . ?
C11 C16 1.410(9) . ?
C11 C17 1.536(7) . ?
C12 C13 1.400(12) . ?
C12 H12A 0.9300 . ?
C16 C15 1.361(8) . ?
C16 H16A 0.9300 . ?
C17 O12 1.233(8) . ?
C17 O11 1.235(7) . ?
C21 C22 1.226(10) . ?
C21 C23 1.420(12) . ?
C21 C24 1.545(10) . ?
C22 C23 1.350(16) 3_545 ?
C22 H22A 0.9300 . ?
C23 C22 1.350(16) 3_545 ?
C23 H23A 0.9300 . ?
C24 O22 1.229(8) . ?
C24 O21 1.239(9) . ?
O22 Zn2 1.964(5) 3 ?
C13 C14 1.384(14) . ?
C13 H13A 0.9300 . ?
C14 C15 1.376(10) . ?
C14 C18 1.494(9) . ?
C15 H15A 0.9300 . ?
C18 O13 1.238(9) . ?
C18 O14 1.243(10) . ?
O13 Zn1 2.002(5) 2_444 ?
O14 Zn2 1.954(5) 4 ?
N1 C2 1.139(17) . ?
N1 C1 1.274(17) . ?
N1 C4 1.41(2) . ?
N1 C3 1.85(2) . ?
N2 C3 1.38(2) . ?
N2 C1 1.40(2) . ?
N2 C5 1.74(2) . ?
C1 H1A 0.9300 . ?
C2 C3 1.21(2) . ?
C2 H2A 0.9300 . ?
C3 H3A 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.45(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.65(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
O13 Zn1 O13 180.0(5) 2_454 4_656 ?
O13 Zn1 O12 85.5(2) 2_454 . ?
O13 Zn1 O12 94.5(2) 4_656 . ?
O13 Zn1 O12 94.5(2) 2_454 3 ?
O13 Zn1 O12 85.5(2) 4_656 3 ?
O12 Zn1 O12 180.0(4) . 3 ?
O13 Zn1 O22 90.8(2) 2_454 3 ?
O13 Zn1 O22 89.2(2) 4_656 3 ?
O12 Zn1 O22 89.0(2) . 3 ?
O12 Zn1 O22 91.0(2) 3 3 ?
O13 Zn1 O22 89.2(2) 2_454 . ?
O13 Zn1 O22 90.8(2) 4_656 . ?
O12 Zn1 O22 91.0(2) . . ?
O12 Zn1 O22 89.0(2) 3 . ?
O22 Zn1 O22 180.0(3) 3 . ?
O14 Zn2 O22 104.9(2) 4_656 3 ?
O14 Zn2 O11 108.9(2) 4_656 . ?
O22 Zn2 O11 104.45(19) 3 . ?
O14 Zn2 I1 108.93(17) 4_656 . ?
O22 Zn2 I1 120.14(15) 3 . ?
O11 Zn2 I1 109.02(15) . . ?
C12 C11 C16 119.3(6) . . ?
C12 C11 C17 122.0(6) . . ?
C16 C11 C17 117.9(5) . . ?
C11 C12 C13 122.9(9) . . ?
C11 C12 H12A 118.6 . . ?
C13 C12 H12A 118.6 . . ?
C15 C16 C11 117.8(6) . . ?
C15 C16 H16A 121.1 . . ?
C11 C16 H16A 121.1 . . ?
O12 C17 O11 125.4(5) . . ?
O12 C17 C11 117.2(6) . . ?
O11 C17 C11 117.4(5) . . ?
C17 O11 Zn2 119.9(4) . . ?
C17 O12 Zn1 143.1(6) . . ?
C22 C21 C23 118.1(9) . . ?
C22 C21 C24 123.1(8) . . ?
C23 C21 C24 118.7(8) . . ?
C23 C22 C21 120.2(10) 3_545 . ?
C23 C22 H22A 119.9 3_545 . ?
C21 C22 H22A 119.9 . . ?
C22 C23 C21 121.7(10) 3_545 . ?
C22 C23 H23A 119.1 3_545 . ?
C21 C23 H23A 119.1 . . ?
O22 C24 O21 122.0(8) . . ?
O22 C24 C21 116.1(6) . . ?
O21 C24 C21 121.9(7) . . ?
C24 O22 Zn2 116.5(5) . 3 ?
C24 O22 Zn1 124.3(6) . . ?
Zn2 O22 Zn1 104.3(2) 3 . ?
C14 C13 C12 116.9(9) . . ?
C14 C13 H13A 121.5 . . ?
C12 C13 H13A 121.5 . . ?
C15 C14 C13 118.3(7) . . ?
C15 C14 C18 121.2(7) . . ?
C13 C14 C18 120.4(7) . . ?
C16 C15 C14 122.1(7) . . ?
C16 C15 H15A 119.0 . . ?
C14 C15 H15A 119.0 . . ?
O13 C18 O14 123.8(6) . . ?
O13 C18 C14 119.0(7) . . ?
O14 C18 C14 117.1(7) . . ?
C18 O13 Zn1 142.1(5) . 2_444 ?
C18 O14 Zn2 124.6(5) . 4 ?
C2 N1 C1 121.2(14) . . ?
C2 N1 C4 119.4(13) . . ?
C1 N1 C4 118.0(12) . . ?
C2 N1 C3 39.4(10) . . ?
C1 N1 C3 82.8(10) . . ?
C4 N1 C3 158.7(10) . . ?
C3 N2 C1 99.0(15) . . ?
C3 N2 C5 142.2(16) . . ?
C1 N2 C5 118.5(13) . . ?
N1 C1 N2 100.6(11) . . ?
N1 C1 H1A 129.7 . . ?
N2 C1 H1A 129.7 . . ?
C3 C2 N1 104.1(15) . . ?
C3 C2 H2A 128.0 . . ?
N1 C2 H2A 128.0 . . ?
C2 C3 N2 113.1(17) . . ?
C2 C3 N1 36.5(9) . . ?
N2 C3 N1 77.6(11) . . ?
C2 C3 H3A 123.4 . . ?
N2 C3 H3A 123.4 . . ?
N1 C3 H3A 157.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N2 100.9(15) . . ?
C6 C5 H5A 111.6 . . ?
N2 C5 H5A 111.6 . . ?
C6 C5 H5B 111.6 . . ?
N2 C5 H5B 111.6 . . ?
H5A C5 H5B 109.4 . . ?
C7 C6 C5 80.6(17) . . ?
C7 C6 H6A 115.2 . . ?
C5 C6 H6A 115.2 . . ?
C7 C6 H6B 115.2 . . ?
C5 C6 H6B 115.2 . . ?
H6A C6 H6B 112.2 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
C16 C11 C12 C13 -19.1(14) . . . . ?
C17 C11 C12 C13 170.8(9) . . . . ?
C12 C11 C16 C15 9.3(12) . . . . ?
C17 C11 C16 C15 179.7(7) . . . . ?
C12 C11 C17 O12 3.0(12) . . . . ?
C16 C11 C17 O12 -167.2(7) . . . . ?
C12 C11 C17 O11 -178.4(8) . . . . ?
C16 C11 C17 O11 11.4(10) . . . . ?
O12 C17 O11 Zn2 -11.1(10) . . . . ?
C11 C17 O11 Zn2 170.5(5) . . . . ?
O14 Zn2 O11 C17 76.3(5) 4_656 . . . ?
O22 Zn2 O11 C17 -35.3(5) 3 . . . ?
I1 Zn2 O11 C17 -164.9(5) . . . . ?
O11 C17 O12 Zn1 31.1(13) . . . . ?
C11 C17 O12 Zn1 -150.5(6) . . . . ?
O13 Zn1 O12 C17 94.6(9) 2_454 . . . ?
O13 Zn1 O12 C17 -85.4(9) 4_656 . . . ?
O12 Zn1 O12 C17 -67(100) 3 . . . ?
O22 Zn1 O12 C17 3.8(8) 3 . . . ?
O22 Zn1 O12 C17 -176.2(8) . . . . ?
C23 C21 C22 C23 -1(2) . . . 3_545 ?
C24 C21 C22 C23 175.7(11) . . . 3_545 ?
C22 C21 C23 C22 1(2) . . . 3_545 ?
C24 C21 C23 C22 -175.8(11) . . . 3_545 ?
C22 C21 C24 O22 23.3(15) . . . . ?
C23 C21 C24 O22 -159.6(10) . . . . ?
C22 C21 C24 O21 -157.4(12) . . . . ?
C23 C21 C24 O21 19.7(16) . . . . ?
O21 C24 O22 Zn2 26.4(13) . . . 3 ?
C21 C24 O22 Zn2 -154.3(6) . . . 3 ?
O21 C24 O22 Zn1 -106.1(10) . . . . ?
C21 C24 O22 Zn1 73.2(9) . . . . ?
O13 Zn1 O22 C24 86.9(5) 2_454 . . . ?
O13 Zn1 O22 C24 -93.1(5) 4_656 . . . ?
O12 Zn1 O22 C24 1.4(5) . . . . ?
O12 Zn1 O22 C24 -178.6(5) 3 . . . ?
O22 Zn1 O22 C24 -110(24) 3 . . . ?
O13 Zn1 O22 Zn2 -50.1(2) 2_454 . . 3 ?
O13 Zn1 O22 Zn2 129.9(2) 4_656 . . 3 ?
O12 Zn1 O22 Zn2 -135.7(2) . . . 3 ?
O12 Zn1 O22 Zn2 44.3(2) 3 . . 3 ?
O22 Zn1 O22 Zn2 113(24) 3 . . 3 ?
C11 C12 C13 C14 19.1(16) . . . . ?
C12 C13 C14 C15 -9.0(14) . . . . ?
C12 C13 C14 C18 167.6(9) . . . . ?
C11 C16 C15 C14 -0.1(12) . . . . ?
C13 C14 C15 C16 0.5(13) . . . . ?
C18 C14 C15 C16 -176.1(7) . . . . ?
C15 C14 C18 O13 -179.8(7) . . . . ?
C13 C14 C18 O13 3.6(12) . . . . ?
C15 C14 C18 O14 -3.6(11) . . . . ?
C13 C14 C18 O14 179.8(8) . . . . ?
O14 C18 O13 Zn1 13.0(14) . . . 2_444 ?
C14 C18 O13 Zn1 -171.1(6) . . . 2_444 ?
O13 C18 O14 Zn2 -17.0(11) . . . 4 ?
C14 C18 O14 Zn2 167.0(5) . . . 4 ?
C2 N1 C1 N2 8.1(18) . . . . ?
C4 N1 C1 N2 174.6(12) . . . . ?
C3 N1 C1 N2 -1.1(11) . . . . ?
C3 N2 C1 N1 1.5(15) . . . . ?
C5 N2 C1 N1 -173.3(12) . . . . ?
C1 N1 C2 C3 -14(2) . . . . ?
C4 N1 C2 C3 179.2(14) . . . . ?
N1 C2 C3 N2 14(2) . . . . ?
C1 N2 C3 C2 -9.8(19) . . . . ?
C5 N2 C3 C2 163(2) . . . . ?
C1 N2 C3 N1 -1.0(10) . . . . ?
C5 N2 C3 N1 171(2) . . . . ?
C1 N1 C3 C2 167.6(18) . . . . ?
C4 N1 C3 C2 -2(3) . . . . ?
C2 N1 C3 N2 -166(2) . . . . ?
C1 N1 C3 N2 1.1(11) . . . . ?
C4 N1 C3 N2 -168(3) . . . . ?
C3 N2 C5 C6 20(3) . . . . ?
C1 N2 C5 C6 -168.7(15) . . . . ?
N2 C5 C6 C7 62.4(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         3.388
_refine_diff_density_min         -1.217
_refine_diff_density_rms         0.264
####################################################################### 
# 
# 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_14
_audit_block_doi                 10.5517/cc1j5jdm
_database_code_depnum_ccdc_archive 'CCDC 1405490'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H12 I2 O12 Zn3, 2(C8 H15 N2)'
_chemical_formula_sum            'C40 H42 I2 N4 O12 Zn3'
_chemical_formula_weight         1220.69

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   13.2721(12)
_cell_length_b                   9.6225(7)
_cell_length_c                   18.4952(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.452(8)
_cell_angle_gamma                90.00
_cell_volume                     2253.3(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1204
_exptl_absorpt_coefficient_mu    3.017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.608
_exptl_absorpt_correction_T_max  0.786
_exptl_absorpt_process_details   'Sphere (CrystalClear)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating-anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9682
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0626
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.73
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3945
_reflns_number_gt                3008
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Corp., 2002)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2002)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2002)'
_computing_structure_solution    'Siemens SHELXTLTM 5'
_computing_structure_refinement  'Siemens SHELXTLTM 5'
_computing_molecular_graphics    'Siemens SHELXTLTM 5'
_computing_publication_material  'Siemens SHELXTLTM 5'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0754P)²+24.1601P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3945
_refine_ls_number_parameters     265
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0715
_refine_ls_wR_factor_ref         0.1920
_refine_ls_wR_factor_gt          0.1770
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.74344(4) 0.95470(6) -0.05788(3) 0.02339(14) Uani 1 1 d . . .
Zn2 Zn 1.0000 1.0000 0.0000 0.02111(19) Uani 1 2 d S . .
I1 I 0.56321(3) 0.83778(6) -0.07882(3) 0.07089(17) Uani 1 1 d . . .
C11 C 0.83245(19) 1.1759(3) -0.22316(12) 0.0306(13) Uani 1 1 d G . .
C12 C 0.92752(19) 1.1882(4) -0.23972(15) 0.0492(18) Uani 1 1 d G . .
H12A H 0.9893 1.1532 -0.2063 0.059 Uiso 1 1 calc R . .
C13 C 0.9302(2) 1.2531(5) -0.30626(18) 0.0449(16) Uani 1 1 d G . .
H13A H 0.9939 1.2614 -0.3173 0.054 Uiso 1 1 calc R . .
C14 C 0.8379(3) 1.3055(4) -0.35625(16) 0.0293(13) Uani 1 1 d G . .
C15 C 0.7428(3) 1.2932(4) -0.33969(15) 0.0376(15) Uani 1 1 d G . .
H15A H 0.6810 1.3283 -0.3731 0.045 Uiso 1 1 calc R . .
C16 C 0.74010(19) 1.2283(4) -0.27315(14) 0.0401(15) Uani 1 1 d G . .
H16A H 0.6765 1.2200 -0.2621 0.048 Uiso 1 1 calc R . .
C17 C 0.8321(4) 1.1068(6) -0.1515(3) 0.0303(13) Uani 1 1 d . . .
C18 C 0.8422(4) 1.3782(5) -0.4273(2) 0.0287(13) Uani 1 1 d . . .
O11 O 0.9185(3) 1.0858(4) -0.1033(2) 0.0438(11) Uani 1 1 d . . .
O12 O 0.7431(3) 1.0715(4) -0.14403(19) 0.0391(10) Uani 1 1 d . . .
O13 O 0.9277(3) 1.3817(4) -0.44010(19) 0.0419(10) Uani 1 1 d . . .
C21 C 0.9394(4) 0.6158(5) -0.0289(3) 0.0317(14) Uani 1 1 d . . .
C22 C 0.9936(5) 0.6121(6) 0.0463(3) 0.0404(16) Uani 1 1 d . . .
H22A H 0.9916 0.6873 0.0775 0.048 Uiso 1 1 calc R . .
C23 C 0.9494(5) 0.5036(5) -0.0751(3) 0.0430(17) Uani 1 1 d . . .
H23A H 0.9160 0.5086 -0.1270 0.052 Uiso 1 1 calc R . .
C24 C 0.8678(4) 0.7356(6) -0.0619(3) 0.0356(14) Uani 1 1 d . . .
O21 O 0.8042(4) 0.7254(5) -0.1252(2) 0.0649(15) Uani 1 1 d . . .
O22 O 0.8744(3) 0.8432(4) -0.01947(19) 0.0299(9) Uani 1 1 d . . .
O24 O 0.7561(3) 1.4239(4) -0.46986(19) 0.0406(11) Uani 1 1 d . . .
N1 N 0.6280(8) 0.3856(9) -0.0803(5) 0.127(3) Uani 1 1 d U . .
N3 N 0.4943(9) 0.2842(9) -0.1657(5) 0.152(4) Uani 1 1 d D . .
C2 C 0.5557(9) 0.2779(11) -0.0982(6) 0.122(4) Uani 1 1 d U . .
H2A H 0.5523 0.2080 -0.0642 0.146 Uiso 1 1 calc R . .
C4 C 0.5246(14) 0.3942(17) -0.1938(8) 0.176(6) Uani 1 1 d U . .
H4A H 0.4948 0.4245 -0.2434 0.211 Uiso 1 1 calc R . .
C5 C 0.6036(14) 0.4586(17) -0.1432(8) 0.174(6) Uani 1 1 d U . .
H5A H 0.6358 0.5407 -0.1510 0.209 Uiso 1 1 calc R . .
C6 C 0.7036(14) 0.4256(18) -0.0079(9) 0.194(8) Uani 1 1 d . . .
H6A H 0.7029 0.3577 0.0299 0.291 Uiso 1 1 calc R . .
H6B H 0.6845 0.5147 0.0073 0.291 Uiso 1 1 calc R . .
H6C H 0.7732 0.4307 -0.0134 0.291 Uiso 1 1 calc R . .
C7 C 0.1921(9) 0.343(2) -0.1479(9) 0.256(3) Uani 1 1 d DU . .
H7A H 0.1718 0.4388 -0.1506 0.384 Uiso 1 1 calc R . .
H7B H 0.2114 0.3121 -0.0962 0.384 Uiso 1 1 calc R . .
H7C H 0.1338 0.2880 -0.1777 0.384 Uiso 1 1 calc R . .
C8 C 0.2830(11) 0.326(2) -0.1776(9) 0.232(9) Uani 1 1 d DU . .
H8A H 0.3399 0.3863 -0.1497 0.279 Uiso 1 1 calc R . .
H8B H 0.2625 0.3540 -0.2304 0.279 Uiso 1 1 calc R . .
C9 C 0.3201(16) 0.1860(16) -0.1716(9) 0.194(8) Uani 1 1 d U . .
H9A H 0.3395 0.1543 -0.1195 0.232 Uiso 1 1 calc R . .
H9B H 0.2666 0.1243 -0.2026 0.232 Uiso 1 1 calc R . .
C10 C 0.4137(11) 0.1912(13) -0.1995(8) 0.164(7) Uani 1 1 d DU . .
H10A H 0.4442 0.0988 -0.1944 0.197 Uiso 1 1 calc R . .
H10B H 0.3891 0.2122 -0.2533 0.197 Uiso 1 1 calc R . .


_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 O12 1.949(4) . ?
Zn1 O24 1.970(4) 4_586 ?
Zn1 O22 1.983(3) . ?
Zn1 I1 2.5656(7) . ?
Zn2 O13 2.020(4) 2_744 ?
Zn2 O13 2.020(4) 4_586 ?
Zn2 O11 2.065(3) 3_775 ?
Zn2 O11 2.065(3) . ?
Zn2 O22 2.197(3) . ?
Zn2 O22 2.197(3) 3_775 ?
C11 C12 1.3900 . ?
C11 C16 1.3900 . ?
C11 C17 1.483(6) . ?
C12 C13 1.3900 . ?
C12 H12A 0.9300 . ?
C13 C14 1.3900 . ?
C13 H13A 0.9300 . ?
C14 C15 1.3900 . ?
C14 C18 1.504(5) . ?
C15 C16 1.3900 . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 O11 1.240(6) . ?
C17 O12 1.276(7) . ?
C18 O13 1.227(6) . ?
C18 O24 1.258(6) . ?
O13 Zn2 2.020(4) 2_754 ?
C21 C22 1.362(7) . ?
C21 C23 1.408(8) . ?
C21 C24 1.502(7) . ?
C22 C23 1.362(8) 3_765 ?
C22 H22A 0.9300 . ?
C23 C22 1.362(8) 3_765 ?
C23 H23A 0.9300 . ?
C24 O21 1.225(6) . ?
C24 O22 1.286(6) . ?
O24 Zn1 1.970(4) 4_585 ?
N1 C5 1.313(16) . ?
N1 C2 1.384(15) . ?
N1 C6 1.464(17) . ?
N3 C4 1.295(18) . ?
N3 C2 1.271(13) . ?
N3 C10 1.391(13) . ?
C2 C4 2.028(18) . ?
C2 H2A 0.9300 . ?
C4 C5 1.33(2) . ?
C4 H4A 0.9300 . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.478(15) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.43(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.48(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?

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
O12 Zn1 O24 108.20(17) . 4_586 ?
O12 Zn1 O22 113.08(16) . . ?
O24 Zn1 O22 100.17(14) 4_586 . ?
O12 Zn1 I1 110.85(11) . . ?
O24 Zn1 I1 103.25(12) 4_586 . ?
O22 Zn1 I1 119.59(10) . . ?
O13 Zn2 O13 180.00(15) 2_744 4_586 ?
O13 Zn2 O11 94.55(16) 2_744 3_775 ?
O13 Zn2 O11 85.45(16) 4_586 3_775 ?
O13 Zn2 O11 85.45(16) 2_744 . ?
O13 Zn2 O11 94.55(16) 4_586 . ?
O11 Zn2 O11 180.0(2) 3_775 . ?
O13 Zn2 O22 89.16(14) 2_744 . ?
O13 Zn2 O22 90.84(14) 4_586 . ?
O11 Zn2 O22 92.20(14) 3_775 . ?
O11 Zn2 O22 87.80(14) . . ?
O13 Zn2 O22 90.84(14) 2_744 3_775 ?
O13 Zn2 O22 89.16(14) 4_586 3_775 ?
O11 Zn2 O22 87.80(14) 3_775 3_775 ?
O11 Zn2 O22 92.20(14) . 3_775 ?
O22 Zn2 O22 180.0 . 3_775 ?
C12 C11 C16 120.0 . . ?
C12 C11 C17 118.8(2) . . ?
C16 C11 C17 121.2(2) . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C14 C13 H13A 120.0 . . ?
C13 C14 C15 120.0 . . ?
C13 C14 C18 119.5(3) . . ?
C15 C14 C18 120.5(3) . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C15 C16 C11 120.0 . . ?
C15 C16 H16A 120.0 . . ?
C11 C16 H16A 120.0 . . ?
O11 C17 O12 124.4(5) . . ?
O11 C17 C11 117.7(5) . . ?
O12 C17 C11 117.9(4) . . ?
O13 C18 O24 126.1(5) . . ?
O13 C18 C14 117.5(4) . . ?
O24 C18 C14 116.4(4) . . ?
C17 O11 Zn2 147.7(4) . . ?
C17 O12 Zn1 117.8(3) . . ?
C18 O13 Zn2 137.8(4) . 2_754 ?
C22 C21 C23 118.9(5) . . ?
C22 C21 C24 120.7(5) . . ?
C23 C21 C24 120.4(4) . . ?
C23 C22 C21 118.8(5) 3_765 . ?
C23 C22 H22A 120.6 3_765 . ?
C21 C22 H22A 120.6 . . ?
C22 C23 C21 122.2(5) 3_765 . ?
C22 C23 H23A 118.9 3_765 . ?
C21 C23 H23A 118.9 . . ?
O21 C24 O22 123.3(5) . . ?
O21 C24 C21 119.8(5) . . ?
O22 C24 C21 116.8(4) . . ?
C24 O22 Zn1 109.0(3) . . ?
C24 O22 Zn2 124.2(3) . . ?
Zn1 O22 Zn2 103.15(15) . . ?
C18 O24 Zn1 124.1(4) . 4_585 ?
C5 N1 C2 102.7(10) . . ?
C5 N1 C6 126.1(12) . . ?
C2 N1 C6 130.7(11) . . ?
C4 N3 C2 104.4(11) . . ?
C4 N3 C10 129.4(11) . . ?
C2 N3 C10 126.2(11) . . ?
N3 C2 N1 113.1(10) . . ?
N3 C2 C4 38.2(7) . . ?
N1 C2 C4 74.9(8) . . ?
N3 C2 H2A 123.4 . . ?
N1 C2 H2A 123.4 . . ?
C4 C2 H2A 161.6 . . ?
N3 C4 C5 111.9(13) . . ?
N3 C4 C2 37.4(6) . . ?
C5 C4 C2 74.5(10) . . ?
N3 C4 H4A 124.1 . . ?
C5 C4 H4A 124.1 . . ?
C2 C4 H4A 161.4 . . ?
C4 C5 N1 107.9(14) . . ?
C4 C5 H5A 126.1 . . ?
N1 C5 H5A 126.1 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C7 C8 C9 112.1(17) . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 104.3(14) . . ?
C10 C9 H9A 110.9 . . ?
C8 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
C8 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
N3 C10 C9 118.5(13) . . ?
N3 C10 H10A 107.7 . . ?
C9 C10 H10A 107.7 . . ?
N3 C10 H10B 107.7 . . ?
C9 C10 H10B 107.7 . . ?
H10A C10 H10B 107.1 . . ?

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
C16 C11 C12 C13 0.0 . . . . ?
C17 C11 C12 C13 -179.7(3) . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C12 C13 C14 C18 178.7(4) . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C18 C14 C15 C16 -178.7(4) . . . . ?
C14 C15 C16 C11 0.0 . . . . ?
C12 C11 C16 C15 0.0 . . . . ?
C17 C11 C16 C15 179.7(3) . . . . ?
C12 C11 C17 O11 12.8(6) . . . . ?
C16 C11 C17 O11 -166.9(4) . . . . ?
C12 C11 C17 O12 -166.3(4) . . . . ?
C16 C11 C17 O12 14.0(6) . . . . ?
C13 C14 C18 O13 3.7(6) . . . . ?
C15 C14 C18 O13 -177.6(4) . . . . ?
C13 C14 C18 O24 -179.6(3) . . . . ?
C15 C14 C18 O24 -0.9(6) . . . . ?
O12 C17 O11 Zn2 3.6(11) . . . . ?
C11 C17 O11 Zn2 -175.5(4) . . . . ?
O13 Zn2 O11 C17 118.5(7) 2_744 . . . ?
O13 Zn2 O11 C17 -61.5(7) 4_586 . . . ?
O11 Zn2 O11 C17 133(100) 3_775 . . . ?
O22 Zn2 O11 C17 29.2(7) . . . . ?
O22 Zn2 O11 C17 -150.8(7) 3_775 . . . ?
O11 C17 O12 Zn1 -8.8(7) . . . . ?
C11 C17 O12 Zn1 170.2(3) . . . . ?
O24 Zn1 O12 C17 85.5(4) 4_586 . . . ?
O22 Zn1 O12 C17 -24.5(4) . . . . ?
I1 Zn1 O12 C17 -162.0(3) . . . . ?
O24 C18 O13 Zn2 26.9(9) . . . 2_754 ?
C14 C18 O13 Zn2 -156.7(4) . . . 2_754 ?
C23 C21 C22 C23 -3.8(10) . . . 3_765 ?
C24 C21 C22 C23 174.5(6) . . . 3_765 ?
C22 C21 C23 C22 4.0(11) . . . 3_765 ?
C24 C21 C23 C22 -174.4(6) . . . 3_765 ?
C22 C21 C24 O21 -165.5(6) . . . . ?
C23 C21 C24 O21 12.9(9) . . . . ?
C22 C21 C24 O22 11.7(8) . . . . ?
C23 C21 C24 O22 -169.9(5) . . . . ?
O21 C24 O22 Zn1 17.0(7) . . . . ?
C21 C24 O22 Zn1 -160.1(4) . . . . ?
O21 C24 O22 Zn2 -104.6(6) . . . . ?
C21 C24 O22 Zn2 78.3(6) . . . . ?
O12 Zn1 O22 C24 -80.4(4) . . . . ?
O24 Zn1 O22 C24 164.7(4) 4_586 . . . ?
I1 Zn1 O22 C24 53.0(4) . . . . ?
O12 Zn1 O22 Zn2 53.27(19) . . . . ?
O24 Zn1 O22 Zn2 -61.64(18) 4_586 . . . ?
I1 Zn1 O22 Zn2 -173.34(7) . . . . ?
O13 Zn2 O22 C24 -5.4(4) 2_744 . . . ?
O13 Zn2 O22 C24 174.6(4) 4_586 . . . ?
O11 Zn2 O22 C24 -99.9(4) 3_775 . . . ?
O11 Zn2 O22 C24 80.1(4) . . . . ?
O22 Zn2 O22 C24 27(100) 3_775 . . . ?
O13 Zn2 O22 Zn1 -129.61(16) 2_744 . . . ?
O13 Zn2 O22 Zn1 50.39(16) 4_586 . . . ?
O11 Zn2 O22 Zn1 135.86(17) 3_775 . . . ?
O11 Zn2 O22 Zn1 -44.14(17) . . . . ?
O22 Zn2 O22 Zn1 -98(100) 3_775 . . . ?
O13 C18 O24 Zn1 -12.8(8) . . . 4_585 ?
C14 C18 O24 Zn1 170.8(3) . . . 4_585 ?
C4 N3 C2 N1 0.4(16) . . . . ?
C10 N3 C2 N1 -179.7(12) . . . . ?
C10 N3 C2 C4 180(2) . . . . ?
C5 N1 C2 N3 0.7(15) . . . . ?
C6 N1 C2 N3 172.5(14) . . . . ?
C5 N1 C2 C4 1.0(12) . . . . ?
C6 N1 C2 C4 172.7(15) . . . . ?
C2 N3 C4 C5 -1(2) . . . . ?
C10 N3 C4 C5 178.7(15) . . . . ?
C10 N3 C4 C2 -180(2) . . . . ?
N1 C2 C4 N3 -179.6(15) . . . . ?
N3 C2 C4 C5 178.6(19) . . . . ?
N1 C2 C4 C5 -1.0(12) . . . . ?
N3 C4 C5 N1 2(2) . . . . ?
C2 C4 C5 N1 1.1(12) . . . . ?
C2 N1 C5 C4 -1.5(18) . . . . ?
C6 N1 C5 C4 -173.8(16) . . . . ?
C7 C8 C9 C10 -176.8(12) . . . . ?
C4 N3 C10 C9 -112.4(19) . . . . ?
C2 N3 C10 C9 67.8(18) . . . . ?
C8 C9 C10 N3 55.0(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.867
_refine_diff_density_min         -1.267
_refine_diff_density_rms         0.167

####################################################################### 
# 
# 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_14
_audit_block_doi                 10.5517/cc1j5jfn
_database_code_depnum_ccdc_archive 'CCDC 1405491'
_audit_update_record             
;
2015-06-08 deposited with the CCDC.
2015-09-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H12 I2 O12 Zn3, 2(C9 H17 N2)'
_chemical_formula_sum            'C42 H46 I2 N4 O12 Zn3'
_chemical_formula_weight         1248.74

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   13.3605(10)
_cell_length_b                   9.8772(4)
_cell_length_c                   18.3026(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.303(7)
_cell_angle_gamma                90.00
_cell_volume                     2293.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.809
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1236
_exptl_absorpt_coefficient_mu    2.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_process_details   'Sphere (CrystalClear)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating-anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9289
_diffrn_reflns_av_R_equivalents  0.0786
_diffrn_reflns_av_sigmaI/netI    0.1273
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.69
_diffrn_reflns_theta_max         25.03
_reflns_number_total             4028
_reflns_number_gt                2361
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Corp., 2002)'
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2002)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2002)'
_computing_structure_solution    'Siemens SHELXTLTM 5'
_computing_structure_refinement  'Siemens SHELXTLTM 5'
_computing_molecular_graphics    'Siemens SHELXTLTM 5'
_computing_publication_material  'Siemens SHELXTLTM 5'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0423P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4028
_refine_ls_number_parameters     286
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1243
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1383
_refine_ls_wR_factor_gt          0.1129
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.25264(5) 0.94764(6) 0.05761(3) 0.02792(18) Uani 1 1 d . . .
Zn2 Zn 0.0000 1.0000 0.0000 0.0263(2) Uani 1 2 d S . .
I1 I 0.42857(4) 0.82941(5) 0.07085(3) 0.05542(16) Uani 1 1 d . . .
O11 O 0.2629(3) 1.0607(4) 0.14900(19) 0.0362(12) Uani 1 1 d . . .
O12 O 0.0887(3) 1.0875(4) 0.10178(19) 0.0401(13) Uani 1 1 d . . .
O13 O 0.2409(3) 1.4255(4) 0.4718(2) 0.0438(13) Uani 1 1 d U . .
O14 O 0.0681(3) 1.3915(4) 0.4347(2) 0.0439(12) Uani 1 1 d . . .
C11 C 0.1726(5) 1.1756(6) 0.2242(3) 0.0299(16) Uani 1 1 d . . .
C12 C 0.2631(5) 1.2258(6) 0.2764(3) 0.0334(16) Uani 1 1 d . . .
H12A H 0.3277 1.2161 0.2677 0.040 Uiso 1 1 calc R . .
C13 C 0.2570(5) 1.2914(6) 0.3424(3) 0.0433(19) Uani 1 1 d . . .
H13A H 0.3180 1.3258 0.3775 0.052 Uiso 1 1 calc R . .
C14 C 0.1636(5) 1.3058(5) 0.3562(3) 0.0260(15) Uani 1 1 d . . .
C15 C 0.0714(5) 1.2563(6) 0.3035(3) 0.0389(18) Uani 1 1 d . . .
H15A H 0.0070 1.2667 0.3123 0.047 Uiso 1 1 calc R . .
C16 C 0.0771(5) 1.1914(6) 0.2378(3) 0.045(2) Uani 1 1 d . . .
H16A H 0.0159 1.1580 0.2023 0.053 Uiso 1 1 calc R . .
C17 C 0.1746(5) 1.1012(5) 0.1522(3) 0.0278(16) Uani 1 1 d . . .
C18 C 0.1567(5) 1.3817(6) 0.4265(3) 0.0349(17) Uani 1 1 d U . .
O21 O 0.1214(3) 0.8372(3) 0.02059(19) 0.0280(10) Uani 1 1 d . . .
O22 O 0.1865(4) 0.7311(4) 0.1320(2) 0.0496(14) Uani 1 1 d . . .
C21 C 0.0546(5) 0.6161(5) 0.0321(3) 0.0284(15) Uani 1 1 d . . .
C22 C -0.0043(5) 0.6125(6) -0.0444(3) 0.0353(17) Uani 1 1 d . . .
H22A H -0.0078 0.6888 -0.0749 0.042 Uiso 1 1 calc R . .
C23 C 0.0578(5) 0.5022(6) 0.0763(3) 0.0356(17) Uani 1 1 d . . .
H23A H 0.0968 0.5033 0.1283 0.043 Uiso 1 1 calc R . .
C24 C 0.1257(5) 0.7341(6) 0.0666(3) 0.0298(16) Uani 1 1 d . . .
N1 N 0.5809(5) 1.2998(6) 0.6865(3) 0.065(2) Uani 1 1 d . . .
N2 N 0.4457(5) 1.1698(6) 0.6388(3) 0.062(2) Uani 1 1 d . . .
C1 C 0.4889(6) 1.2857(8) 0.6320(4) 0.062(3) Uani 1 1 d . . .
H1A H 0.4591 1.3497 0.5942 0.074 Uiso 1 1 calc R . .
C2 C 0.5959(7) 1.1835(8) 0.7279(4) 0.073(3) Uani 1 1 d . . .
H2A H 0.6544 1.1643 0.7701 0.088 Uiso 1 1 calc R . .
C3 C 0.5158(7) 1.1025(9) 0.6996(4) 0.083(3) Uani 1 1 d . . .
H3A H 0.5077 1.0161 0.7171 0.099 Uiso 1 1 calc R . .
C4 C 0.6549(7) 1.4101(8) 0.6950(5) 0.099(4) Uani 1 1 d . . .
H4A H 0.6233 1.4806 0.6591 0.149 Uiso 1 1 calc R . .
H4B H 0.7173 1.3778 0.6852 0.149 Uiso 1 1 calc R . .
H4C H 0.6734 1.4451 0.7465 0.149 Uiso 1 1 calc R . .
C5 C 0.3479(7) 1.1153(8) 0.5862(4) 0.079(3) Uani 1 1 d . . .
H5A H 0.2956 1.1868 0.5724 0.095 Uiso 1 1 calc R . .
H5B H 0.3216 1.0451 0.6124 0.095 Uiso 1 1 calc R . .
C6 C 0.3618(6) 1.0584(7) 0.5153(4) 0.057(2) Uani 1 1 d . . .
H6A H 0.4196 0.9940 0.5292 0.068 Uiso 1 1 calc R . .
H6B H 0.3806 1.1308 0.4862 0.068 Uiso 1 1 calc R . .
C7 C 0.2621(6) 0.9873(7) 0.4640(4) 0.058(2) Uani 1 1 d . . .
H7A H 0.2423 0.9170 0.4939 0.070 Uiso 1 1 calc R . .
H7B H 0.2050 1.0526 0.4493 0.070 Uiso 1 1 calc R . .
C8 C 0.2744(6) 0.9254(7) 0.3928(4) 0.063(2) Uani 1 1 d . . .
H8A H 0.3317 0.8604 0.4075 0.075 Uiso 1 1 calc R . .
H8B H 0.2938 0.9958 0.3628 0.075 Uiso 1 1 calc R . .
C9 C 0.1754(7) 0.8542(8) 0.3422(4) 0.087(3) Uani 1 1 d . . .
H9A H 0.1882 0.8191 0.2971 0.131 Uiso 1 1 calc R . .
H9B H 0.1182 0.9177 0.3273 0.131 Uiso 1 1 calc R . .
H9C H 0.1576 0.7812 0.3705 0.131 Uiso 1 1 calc R . .


_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 O13 1.976(4) 4_585 ?
Zn1 O11 1.980(3) . ?
Zn1 O21 1.995(4) . ?
Zn1 I1 2.5669(9) . ?
Zn2 O14 2.022(4) 4_585 ?
Zn2 O14 2.022(4) 2_545 ?
Zn2 O12 2.058(3) 3_575 ?
Zn2 O12 2.058(3) . ?
Zn2 O21 2.230(4) 3_575 ?
Zn2 O21 2.230(4) . ?
O11 C17 1.264(7) . ?
O12 C17 1.234(6) . ?
O13 C18 1.246(7) . ?
O13 Zn1 1.976(4) 4_586 ?
O14 C18 1.242(7) . ?
O14 Zn2 2.022(4) 2 ?
C11 C12 1.376(7) . ?
C11 C16 1.383(9) . ?
C11 C17 1.518(7) . ?
C12 C13 1.395(7) . ?
C12 H12A 0.9300 . ?
C13 C14 1.357(8) . ?
C13 H13A 0.9300 . ?
C14 C15 1.392(8) . ?
C14 C18 1.517(7) . ?
C15 C16 1.387(8) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
O21 C24 1.312(6) . ?
O22 C24 1.217(6) . ?
C21 C22 1.375(7) . ?
C21 C23 1.379(7) . ?
C21 C24 1.511(8) . ?
C22 C23 1.368(8) 3_565 ?
C22 H22A 0.9300 . ?
C23 C22 1.368(8) 3_565 ?
C23 H23A 0.9300 . ?
N1 C1 1.324(9) . ?
N1 C2 1.356(9) . ?
N1 C4 1.446(10) . ?
N2 C1 1.306(9) . ?
N2 C3 1.379(9) . ?
N2 C5 1.460(9) . ?
C1 H1A 0.9300 . ?
C2 C3 1.305(11) . ?
C2 H2A 0.9300 . ?
C3 H3A 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.480(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.537(9) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.495(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.527(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
O13 Zn1 O11 106.32(16) 4_585 . ?
O13 Zn1 O21 103.56(15) 4_585 . ?
O11 Zn1 O21 114.56(16) . . ?
O13 Zn1 I1 101.85(13) 4_585 . ?
O11 Zn1 I1 111.02(12) . . ?
O21 Zn1 I1 117.69(11) . . ?
O14 Zn2 O14 180.0 4_585 2_545 ?
O14 Zn2 O12 85.73(16) 4_585 3_575 ?
O14 Zn2 O12 94.27(16) 2_545 3_575 ?
O14 Zn2 O12 94.27(16) 4_585 . ?
O14 Zn2 O12 85.73(16) 2_545 . ?
O12 Zn2 O12 180.00(14) 3_575 . ?
O14 Zn2 O21 87.51(15) 4_585 3_575 ?
O14 Zn2 O21 92.49(15) 2_545 3_575 ?
O12 Zn2 O21 88.21(14) 3_575 3_575 ?
O12 Zn2 O21 91.79(14) . 3_575 ?
O14 Zn2 O21 92.49(15) 4_585 . ?
O14 Zn2 O21 87.51(15) 2_545 . ?
O12 Zn2 O21 91.79(14) 3_575 . ?
O12 Zn2 O21 88.21(14) . . ?
O21 Zn2 O21 180.00(18) 3_575 . ?
C17 O11 Zn1 113.5(3) . . ?
C17 O12 Zn2 149.2(4) . . ?
C18 O13 Zn1 125.4(4) . 4_586 ?
C18 O14 Zn2 137.3(4) . 2 ?
C12 C11 C16 119.6(5) . . ?
C12 C11 C17 121.8(6) . . ?
C16 C11 C17 118.7(5) . . ?
C11 C12 C13 119.4(6) . . ?
C11 C12 H12A 120.3 . . ?
C13 C12 H12A 120.3 . . ?
C14 C13 C12 121.2(5) . . ?
C14 C13 H13A 119.4 . . ?
C12 C13 H13A 119.4 . . ?
C13 C14 C15 120.0(5) . . ?
C13 C14 C18 121.0(5) . . ?
C15 C14 C18 119.0(5) . . ?
C16 C15 C14 119.0(6) . . ?
C16 C15 H15A 120.5 . . ?
C14 C15 H15A 120.5 . . ?
C11 C16 C15 120.9(5) . . ?
C11 C16 H16A 119.6 . . ?
C15 C16 H16A 119.6 . . ?
O12 C17 O11 126.4(5) . . ?
O12 C17 C11 115.9(6) . . ?
O11 C17 C11 117.7(5) . . ?
O14 C18 O13 126.0(5) . . ?
O14 C18 C14 117.1(5) . . ?
O13 C18 C14 117.0(6) . . ?
C24 O21 Zn1 110.5(3) . . ?
C24 O21 Zn2 123.5(4) . . ?
Zn1 O21 Zn2 100.27(14) . . ?
C22 C21 C23 118.6(5) . . ?
C22 C21 C24 122.0(5) . . ?
C23 C21 C24 118.9(5) . . ?
C23 C22 C21 120.7(5) 3_565 . ?
C23 C22 H22A 119.6 3_565 . ?
C21 C22 H22A 119.6 . . ?
C22 C23 C21 120.7(5) 3_565 . ?
C22 C23 H23A 119.7 3_565 . ?
C21 C23 H23A 119.7 . . ?
O22 C24 O21 122.1(5) . . ?
O22 C24 C21 122.1(5) . . ?
O21 C24 C21 115.8(4) . . ?
C1 N1 C2 105.7(7) . . ?
C1 N1 C4 127.0(7) . . ?
C2 N1 C4 127.0(7) . . ?
C1 N2 C3 106.9(7) . . ?
C1 N2 C5 126.2(6) . . ?
C3 N2 C5 126.5(7) . . ?
N2 C1 N1 110.7(7) . . ?
N2 C1 H1A 124.6 . . ?
N1 C1 H1A 124.6 . . ?
C3 C2 N1 109.8(7) . . ?
C3 C2 H2A 125.1 . . ?
N1 C2 H2A 125.1 . . ?
C2 C3 N2 106.8(7) . . ?
C2 C3 H3A 126.6 . . ?
N2 C3 H3A 126.6 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C5 C6 112.7(7) . . ?
N2 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N2 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C5 C6 C7 112.7(6) . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C6 114.0(6) . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 C9 113.9(7) . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
O13 Zn1 O11 C17 82.3(4) 4_585 . . . ?
O21 Zn1 O11 C17 -31.5(4) . . . . ?
I1 Zn1 O11 C17 -167.7(3) . . . . ?
O14 Zn2 O12 C17 -71.1(8) 4_585 . . . ?
O14 Zn2 O12 C17 108.9(8) 2_545 . . . ?
O12 Zn2 O12 C17 130(17) 3_575 . . . ?
O21 Zn2 O12 C17 -158.7(8) 3_575 . . . ?
O21 Zn2 O12 C17 21.3(8) . . . . ?
C16 C11 C12 C13 0.3(9) . . . . ?
C17 C11 C12 C13 -178.9(5) . . . . ?
C11 C12 C13 C14 0.3(9) . . . . ?
C12 C13 C14 C15 -0.8(9) . . . . ?
C12 C13 C14 C18 -177.7(5) . . . . ?
C13 C14 C15 C16 0.7(9) . . . . ?
C18 C14 C15 C16 177.6(5) . . . . ?
C12 C11 C16 C15 -0.4(9) . . . . ?
C17 C11 C16 C15 178.7(5) . . . . ?
C14 C15 C16 C11 0.0(9) . . . . ?
Zn2 O12 C17 O11 11.4(12) . . . . ?
Zn2 O12 C17 C11 -169.4(5) . . . . ?
Zn1 O11 C17 O12 -7.4(7) . . . . ?
Zn1 O11 C17 C11 173.5(4) . . . . ?
C12 C11 C17 O12 -164.4(5) . . . . ?
C16 C11 C17 O12 16.5(8) . . . . ?
C12 C11 C17 O11 14.9(8) . . . . ?
C16 C11 C17 O11 -164.3(5) . . . . ?
Zn2 O14 C18 O13 15.2(10) 2 . . . ?
Zn2 O14 C18 C14 -166.7(4) 2 . . . ?
Zn1 O13 C18 O14 -12.7(8) 4_586 . . . ?
Zn1 O13 C18 C14 169.3(3) 4_586 . . . ?
C13 C14 C18 O14 179.4(5) . . . . ?
C15 C14 C18 O14 2.5(8) . . . . ?
C13 C14 C18 O13 -2.4(8) . . . . ?
C15 C14 C18 O13 -179.3(5) . . . . ?
O13 Zn1 O21 C24 170.1(4) 4_585 . . . ?
O11 Zn1 O21 C24 -74.5(4) . . . . ?
I1 Zn1 O21 C24 58.7(4) . . . . ?
O13 Zn1 O21 Zn2 -58.12(18) 4_585 . . . ?
O11 Zn1 O21 Zn2 57.23(18) . . . . ?
I1 Zn1 O21 Zn2 -169.54(6) . . . . ?
O14 Zn2 O21 C24 174.9(4) 4_585 . . . ?
O14 Zn2 O21 C24 -5.1(4) 2_545 . . . ?
O12 Zn2 O21 C24 -99.3(4) 3_575 . . . ?
O12 Zn2 O21 C24 80.7(4) . . . . ?
O21 Zn2 O21 C24 43(40) 3_575 . . . ?
O14 Zn2 O21 Zn1 51.81(16) 4_585 . . . ?
O14 Zn2 O21 Zn1 -128.19(16) 2_545 . . . ?
O12 Zn2 O21 Zn1 137.62(17) 3_575 . . . ?
O12 Zn2 O21 Zn1 -42.38(17) . . . . ?
O21 Zn2 O21 Zn1 -80(40) 3_575 . . . ?
C23 C21 C22 C23 -0.6(10) . . . 3_565 ?
C24 C21 C22 C23 171.9(6) . . . 3_565 ?
C22 C21 C23 C22 0.6(10) . . . 3_565 ?
C24 C21 C23 C22 -172.1(6) . . . 3_565 ?
Zn1 O21 C24 O22 18.9(7) . . . . ?
Zn2 O21 C24 O22 -99.4(6) . . . . ?
Zn1 O21 C24 C21 -158.0(4) . . . . ?
Zn2 O21 C24 C21 83.6(5) . . . . ?
C22 C21 C24 O22 -171.7(6) . . . . ?
C23 C21 C24 O22 0.7(9) . . . . ?
C22 C21 C24 O21 5.2(9) . . . . ?
C23 C21 C24 O21 177.7(5) . . . . ?
C3 N2 C1 N1 -2.3(9) . . . . ?
C5 N2 C1 N1 -175.5(7) . . . . ?
C2 N1 C1 N2 1.5(9) . . . . ?
C4 N1 C1 N2 175.8(7) . . . . ?
C1 N1 C2 C3 -0.1(10) . . . . ?
C4 N1 C2 C3 -174.3(8) . . . . ?
N1 C2 C3 N2 -1.3(10) . . . . ?
C1 N2 C3 C2 2.2(10) . . . . ?
C5 N2 C3 C2 175.4(7) . . . . ?
C1 N2 C5 C6 77.7(10) . . . . ?
C3 N2 C5 C6 -94.2(9) . . . . ?
N2 C5 C6 C7 173.7(6) . . . . ?
C5 C6 C7 C8 -178.5(6) . . . . ?
C6 C7 C8 C9 179.7(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.110
_refine_diff_density_min         -0.642
_refine_diff_density_rms         0.148

