# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_audit_block_doi                 10.5517/ccdc.csd.cc1zdybn
_database_code_depnum_ccdc_archive 'CCDC 1829692'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 Cl N4 O Zn, Cl O4'
_chemical_formula_sum            'C16 H18 Cl2 N4 O5 Zn'
_chemical_formula_weight         482.61

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.6472(4)
_cell_length_b                   15.7209(5)
_cell_length_c                   11.7623(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.4470(10)
_cell_angle_gamma                90
_cell_volume                     1952.21(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1542
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.02

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    1.568
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.562
_exptl_absorpt_correction_T_max  0.681
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_absorpt_special_details   ?


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29595
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.174
_diffrn_reflns_theta_max         28.924
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5147
_reflns_number_gt                4092
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 for Windows (Farrugia,1997)'
_computing_publication_material  'Wingx 2013.03 (Farrugia, 1999)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0711P)²+1.2300P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5147
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.93255(3) 0.78710(2) 0.85358(2) 0.03576(11) Uani 1 1 d . . . . .
Cl1 Cl 0.92344(6) 0.86158(4) 0.69192(5) 0.04313(16) Uani 1 1 d . . . . .
N1 N 0.8044(2) 0.69329(14) 0.87966(19) 0.0414(5) Uani 1 1 d . . . . .
N2 N 1.0432(2) 0.66801(15) 0.8178(2) 0.0432(5) Uani 1 1 d . . . . .
N3 N 1.0839(2) 0.79193(15) 0.9814(2) 0.0445(5) Uani 1 1 d . . . . .
N4 N 0.8757(2) 0.88442(14) 0.97020(18) 0.0411(5) Uani 1 1 d . . . . .
C1 C 0.7028(3) 0.7057(2) 0.9330(3) 0.0529(7) Uani 1 1 d . . . . .
H1 H 0.6803 0.7610 0.9496 0.063 Uiso 1 1 calc R U . . .
C2 C 0.6292(3) 0.6387(2) 0.9647(3) 0.0648(9) Uani 1 1 d . . . . .
H2 H 0.5592 0.6489 1.0025 0.078 Uiso 1 1 calc R U . . .
C3 C 0.6626(3) 0.5569(2) 0.9387(3) 0.0634(9) Uani 1 1 d . . . . .
H3 H 0.6151 0.5109 0.9586 0.076 Uiso 1 1 calc R U . . .
C4 C 0.7666(3) 0.54407(19) 0.8830(3) 0.0534(7) Uani 1 1 d . . . . .
H4 H 0.7905 0.4893 0.8649 0.064 Uiso 1 1 calc R U . . .
C5 C 0.8349(3) 0.61327(17) 0.8546(2) 0.0422(5) Uani 1 1 d . . . . .
C6 C 0.9455(3) 0.60301(18) 0.7882(3) 0.0481(6) Uani 1 1 d . . . . .
H6 H 0.9815 0.5457 0.7982 0.058 Uiso 1 1 calc R U . . .
O1 O 0.9023(2) 0.61950(16) 0.67097(19) 0.0602(6) Uani 1 1 d . . . . .
C7 C 1.0081(3) 0.6492(3) 0.6180(3) 0.0660(9) Uani 1 1 d . . . . .
H7A H 0.9843 0.6985 0.5704 0.079 Uiso 1 1 calc R U . . .
H7B H 1.0379 0.6050 0.5706 0.079 Uiso 1 1 calc R U . . .
C8 C 1.1106(3) 0.6726(2) 0.7154(3) 0.0594(8) Uani 1 1 d . . . . .
H8A H 1.1803 0.6325 0.7209 0.071 Uiso 1 1 calc R U . . .
H8B H 1.1428 0.7295 0.7053 0.071 Uiso 1 1 calc R U . . .
C9 C 1.1249(3) 0.6499(2) 0.9260(3) 0.0544(7) Uani 1 1 d . . . . .
H9A H 1.1902 0.6096 0.9120 0.065 Uiso 1 1 calc R U . . .
H9B H 1.0748 0.6247 0.9805 0.065 Uiso 1 1 calc R U . . .
C10 C 1.1862(3) 0.7319(2) 0.9757(3) 0.0575(8) Uani 1 1 d . . . . .
H10A H 1.2312 0.7218 1.0516 0.069 Uiso 1 1 calc R U . . .
H10B H 1.2456 0.7537 0.9269 0.069 Uiso 1 1 calc R U . . .
C11 C 1.0733(3) 0.83719(19) 1.0673(2) 0.0492(6) Uani 1 1 d . . . . .
H11 H 1.1337 0.8351 1.1318 0.059 Uiso 1 1 calc R U . . .
C12 C 0.9624(3) 0.89386(18) 1.0632(2) 0.0450(6) Uani 1 1 d . . . . .
C13 C 0.9479(3) 0.9540(2) 1.1468(3) 0.0567(8) Uani 1 1 d . . . . .
H13 H 1.0086 0.9591 1.2109 0.068 Uiso 1 1 calc R U . . .
C14 C 0.8444(3) 1.0057(2) 1.1345(3) 0.0594(8) Uani 1 1 d . . . . .
H14 H 0.8331 1.0459 1.1903 0.071 Uiso 1 1 calc R U . . .
C15 C 0.7566(3) 0.99752(19) 1.0383(3) 0.0542(7) Uani 1 1 d . . . . .
H15 H 0.6858 1.0326 1.0275 0.065 Uiso 1 1 calc R U . . .
C16 C 0.7757(3) 0.93645(18) 0.9584(3) 0.0468(6) Uani 1 1 d . . . . .
H16 H 0.7164 0.9312 0.8934 0.056 Uiso 1 1 calc R U . . .
Cl2 Cl 0.94622(8) 0.65208(6) 0.23832(7) 0.0599(2) Uani 1 1 d . . . . .
O2 O 0.9027(6) 0.7303(4) 0.2160(9) 0.243(5) Uani 1 1 d . . . . .
O3 O 1.0761(4) 0.6511(4) 0.2201(5) 0.1515(19) Uani 1 1 d . . . . .
O4 O 0.9499(6) 0.6196(6) 0.3429(4) 0.224(4) Uani 1 1 d . . . . .
O5 O 0.8873(8) 0.5936(5) 0.1629(6) 0.252(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N3 2.058(2) . ?
Zn1 N1 2.059(2) . ?
Zn1 N4 2.192(2) . ?
Zn1 Cl1 2.2245(7) . ?
Zn1 N2 2.280(2) . ?
N1 C1 1.333(4) . ?
N1 C5 1.342(3) . ?
N2 C6 1.468(4) . ?
N2 C9 1.472(4) . ?
N2 C8 1.482(4) . ?
N3 C11 1.253(4) . ?
N3 C10 1.449(4) . ?
N4 C16 1.335(4) . ?
N4 C12 1.345(3) . ?
C1 C2 1.392(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.378(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.503(4) . ?
C6 O1 1.420(4) . ?
C6 H6 0.9800 . ?
O1 C7 1.434(4) . ?
C7 C8 1.521(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.527(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.475(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.388(4) . ?
C13 C14 1.361(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
Cl2 O4 1.327(4) . ?
Cl2 O2 1.328(5) . ?
Cl2 O5 1.372(5) . ?
Cl2 O3 1.427(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 Zn1 N1 112.89(9) . . ?
N3 Zn1 N4 76.76(9) . . ?
N1 Zn1 N4 99.47(8) . . ?
N3 Zn1 Cl1 123.25(7) . . ?
N1 Zn1 Cl1 123.23(7) . . ?
N4 Zn1 Cl1 100.52(6) . . ?
N3 Zn1 N2 77.91(9) . . ?
N1 Zn1 N2 78.89(9) . . ?
N4 Zn1 N2 151.63(8) . . ?
Cl1 Zn1 N2 103.94(6) . . ?
C1 N1 C5 118.3(2) . . ?
C1 N1 Zn1 124.02(19) . . ?
C5 N1 Zn1 117.07(18) . . ?
C6 N2 C9 113.1(2) . . ?
C6 N2 C8 104.1(2) . . ?
C9 N2 C8 114.7(2) . . ?
C6 N2 Zn1 104.37(16) . . ?
C9 N2 Zn1 105.12(17) . . ?
C8 N2 Zn1 115.21(19) . . ?
C11 N3 C10 123.6(2) . . ?
C11 N3 Zn1 117.8(2) . . ?
C10 N3 Zn1 117.69(19) . . ?
C16 N4 C12 118.1(2) . . ?
C16 N4 Zn1 130.09(18) . . ?
C12 N4 Zn1 111.68(19) . . ?
N1 C1 C2 122.3(3) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 118.4(3) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 119.0(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 122.5(3) . . ?
N1 C5 C6 116.3(2) . . ?
C4 C5 C6 121.1(3) . . ?
O1 C6 N2 103.5(2) . . ?
O1 C6 C5 107.9(2) . . ?
N2 C6 C5 112.4(2) . . ?
O1 C6 H6 110.9 . . ?
N2 C6 H6 110.9 . . ?
C5 C6 H6 110.9 . . ?
C6 O1 C7 107.9(2) . . ?
O1 C7 C8 106.2(3) . . ?
O1 C7 H7A 110.5 . . ?
C8 C7 H7A 110.5 . . ?
O1 C7 H7B 110.5 . . ?
C8 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
N2 C8 C7 103.0(2) . . ?
N2 C8 H8A 111.2 . . ?
C7 C8 H8A 111.2 . . ?
N2 C8 H8B 111.2 . . ?
C7 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
N2 C9 C10 110.1(2) . . ?
N2 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
N2 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.2 . . ?
N3 C10 C9 106.3(2) . . ?
N3 C10 H10A 110.5 . . ?
C9 C10 H10A 110.5 . . ?
N3 C10 H10B 110.5 . . ?
C9 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?
N3 C11 C12 118.2(2) . . ?
N3 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
N4 C12 C13 121.6(3) . . ?
N4 C12 C11 115.0(2) . . ?
C13 C12 C11 123.4(3) . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 119.0(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C16 C15 C14 118.8(3) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
N4 C16 C15 122.9(3) . . ?
N4 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
O4 Cl2 O2 120.5(6) . . ?
O4 Cl2 O5 107.3(5) . . ?
O2 Cl2 O5 111.9(5) . . ?
O4 Cl2 O3 102.8(4) . . ?
O2 Cl2 O3 107.5(4) . . ?
O5 Cl2 O3 105.4(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 1.0(5) . . . . ?
Zn1 N1 C1 C2 -169.9(3) . . . . ?
N1 C1 C2 C3 -0.6(6) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C1 N1 C5 C4 -0.9(4) . . . . ?
Zn1 N1 C5 C4 170.6(2) . . . . ?
C1 N1 C5 C6 176.4(3) . . . . ?
Zn1 N1 C5 C6 -12.0(3) . . . . ?
C3 C4 C5 N1 0.4(4) . . . . ?
C3 C4 C5 C6 -176.8(3) . . . . ?
C9 N2 C6 O1 -164.8(2) . . . . ?
C8 N2 C6 O1 -39.7(3) . . . . ?
Zn1 N2 C6 O1 81.5(2) . . . . ?
C9 N2 C6 C5 79.0(3) . . . . ?
C8 N2 C6 C5 -155.9(2) . . . . ?
Zn1 N2 C6 C5 -34.7(3) . . . . ?
N1 C5 C6 O1 -79.8(3) . . . . ?
C4 C5 C6 O1 97.6(3) . . . . ?
N1 C5 C6 N2 33.7(3) . . . . ?
C4 C5 C6 N2 -148.9(3) . . . . ?
N2 C6 O1 C7 33.9(3) . . . . ?
C5 C6 O1 C7 153.2(3) . . . . ?
C6 O1 C7 C8 -14.8(4) . . . . ?
C6 N2 C8 C7 29.9(3) . . . . ?
C9 N2 C8 C7 154.0(3) . . . . ?
Zn1 N2 C8 C7 -83.8(3) . . . . ?
O1 C7 C8 N2 -9.8(4) . . . . ?
C6 N2 C9 C10 -157.6(2) . . . . ?
C8 N2 C9 C10 83.2(3) . . . . ?
Zn1 N2 C9 C10 -44.4(3) . . . . ?
C11 N3 C10 C9 133.9(3) . . . . ?
Zn1 N3 C10 C9 -34.9(3) . . . . ?
N2 C9 C10 N3 52.7(3) . . . . ?
C10 N3 C11 C12 -178.2(3) . . . . ?
Zn1 N3 C11 C12 -9.3(3) . . . . ?
C16 N4 C12 C13 1.8(4) . . . . ?
Zn1 N4 C12 C13 177.9(2) . . . . ?
C16 N4 C12 C11 -176.9(2) . . . . ?
Zn1 N4 C12 C11 -0.9(3) . . . . ?
N3 C11 C12 N4 6.7(4) . . . . ?
N3 C11 C12 C13 -172.1(3) . . . . ?
N4 C12 C13 C14 -0.8(4) . . . . ?
C11 C12 C13 C14 177.9(3) . . . . ?
C12 C13 C14 C15 -0.6(5) . . . . ?
C13 C14 C15 C16 0.9(5) . . . . ?
C12 N4 C16 C15 -1.6(4) . . . . ?
Zn1 N4 C16 C15 -176.8(2) . . . . ?
C14 C15 C16 N4 0.2(5) . . . . ?

_refine_diff_density_max         0.855
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.074

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_audit_block_doi                 10.5517/ccdc.csd.cc1zdycp
_database_code_depnum_ccdc_archive 'CCDC 1829693'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 Br N4 O2 Zn, Br3 H2 O Zn, 2(H2 O)'
_chemical_formula_sum            'C16 H24 Br4 N4 O4 Zn2'
_chemical_formula_weight         786.77

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.150(3)
_cell_length_b                   13.665(5)
_cell_length_c                   14.519(5)
_cell_angle_alpha                67.354(4)
_cell_angle_beta                 78.378(4)
_cell_angle_gamma                88.647(5)
_cell_volume                     1280.2(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1194
_cell_measurement_theta_max      24.46
_cell_measurement_theta_min      2.06

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.041
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    8.144
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.102
_exptl_absorpt_correction_T_max  0.187
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4535
_diffrn_reflns_av_unetI/netI     0.0971
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.554
_diffrn_reflns_theta_max         25.537
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             4535
_reflns_number_gt                2585
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELX97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 for Windows (Farrugia,1997)'
_computing_publication_material  'Wingx 2013.03 (Farrugia, 1999)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1968P)²+5.6222P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4535
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1448
_refine_ls_R_factor_gt           0.0880
_refine_ls_wR_factor_ref         0.3391
_refine_ls_wR_factor_gt          0.2610
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.8598(2) 0.70012(15) 0.63570(16) 0.0471(6) Uani 1 1 d . . . . .
Br1 Br 0.5754(2) 0.71609(15) 0.57354(16) 0.0612(6) Uani 1 1 d . . . . .
N1 N 1.0129(16) 0.8350(11) 0.6208(11) 0.048(3) Uani 1 1 d . . . . .
N2 N 0.7703(17) 0.7044(11) 0.7909(12) 0.055(4) Uani 1 1 d . . . . .
N3 N 0.9584(18) 0.5610(11) 0.7263(12) 0.059(4) Uani 1 1 d . . . . .
N4 N 1.0573(16) 0.6558(11) 0.5241(11) 0.045(3) Uani 1 1 d . . . . .
O1 O 0.6352(16) 0.8626(10) 0.7501(12) 0.073(4) Uani 1 1 d . . . . .
C1 C 1.151(2) 0.8887(11) 0.5385(12) 0.043(4) Uani 1 1 d . . . . .
H1 H 1.1810 0.8657 0.4851 0.051 Uiso 1 1 calc R U . . .
C2 C 1.247(2) 0.9780(13) 0.5333(15) 0.054(4) Uani 1 1 d . . . . .
H2 H 1.3385 1.0157 0.4754 0.065 Uiso 1 1 calc R U . . .
C3 C 1.209(2) 1.0116(15) 0.6117(16) 0.061(5) Uani 1 1 d . . . . .
H3 H 1.2773 1.0695 0.6099 0.073 Uiso 1 1 calc R U . . .
C4 C 1.067(2) 0.9572(13) 0.6926(14) 0.055(4) Uani 1 1 d . . . . .
H4 H 1.0331 0.9792 0.7467 0.066 Uiso 1 1 calc R U . . .
C5 C 0.973(2) 0.8701(13) 0.6945(12) 0.043(4) Uani 1 1 d . . . . .
C6 C 0.804(2) 0.8118(13) 0.7818(13) 0.051(4) Uani 1 1 d . . . . .
H6 H 0.8189 0.8144 0.8465 0.061 Uiso 1 1 calc R U . . .
C7 C 0.477(3) 0.7852(15) 0.8038(18) 0.078(6) Uani 1 1 d . . . . .
H7A H 0.3940 0.7861 0.7582 0.094 Uiso 1 1 calc R U . . .
H7B H 0.4020 0.8006 0.8598 0.094 Uiso 1 1 calc R U . . .
C8 C 0.561(2) 0.6779(15) 0.8439(15) 0.064(5) Uani 1 1 d . . . . .
H8A H 0.5034 0.6268 0.8249 0.077 Uiso 1 1 calc R U . . .
H8B H 0.5458 0.6502 0.9175 0.077 Uiso 1 1 calc R U . . .
C9 C 0.892(3) 0.6293(15) 0.8523(15) 0.062(5) Uani 1 1 d . . . . .
H9A H 0.8402 0.6127 0.9240 0.074 Uiso 1 1 calc R U . . .
H9B H 1.0193 0.6630 0.8357 0.074 Uiso 1 1 calc R U . . .
C10 C 0.908(3) 0.5290(14) 0.8346(13) 0.056(4) Uani 1 1 d . . . . .
H10A H 1.0049 0.4867 0.8668 0.067 Uiso 1 1 calc R U . . .
H10B H 0.7864 0.4874 0.8621 0.067 Uiso 1 1 calc R U . . .
C11 C 1.081(2) 0.5159(13) 0.6781(14) 0.051(4) Uani 1 1 d . . . . .
H11A H 1.1338 0.4535 0.7141 0.062 Uiso 1 1 calc R U . . .
C12 C 1.134(2) 0.5645(12) 0.5660(12) 0.042(4) Uani 1 1 d . . . . .
C13 C 1.251(2) 0.5107(14) 0.5158(14) 0.050(4) Uani 1 1 d . . . . .
H13 H 1.2968 0.4452 0.5500 0.060 Uiso 1 1 calc R U . . .
C14 C 1.295(2) 0.5635(16) 0.4074(19) 0.072(6) Uani 1 1 d . . . . .
H14 H 1.3790 0.5339 0.3688 0.086 Uiso 1 1 calc R U . . .
C15 C 1.217(3) 0.6568(16) 0.3593(16) 0.063(5) Uani 1 1 d . . . . .
H15 H 1.2420 0.6899 0.2885 0.075 Uiso 1 1 calc R U . . .
C16 C 1.098(2) 0.7007(17) 0.4210(19) 0.068(6) Uani 1 1 d . . . . .
H16 H 1.0443 0.7643 0.3891 0.082 Uiso 1 1 calc R U . . .
Zn2 Zn 0.2435(3) 0.23696(16) 0.89785(16) 0.0528(6) Uani 1 1 d . . . . .
Br2 Br -0.0668(3) 0.2147(2) 0.9990(2) 0.0897(8) Uani 1 1 d . . . . .
Br3 Br 0.2343(3) 0.2003(2) 0.75097(19) 0.0794(7) Uani 1 1 d . . . . .
Br4 Br 0.4135(3) 0.39864(16) 0.85907(17) 0.0692(6) Uani 1 1 d . . . . .
O1W O 0.3945(18) 0.1297(10) 0.9853(10) 0.069(3) Uani 1 1 d . . . . .
H11 H 0.4994 0.1138 0.9592 0.104 Uiso 1 1 d R U . . .
H12 H 0.3549 0.0658 1.0238 0.104 Uiso 1 1 d R U . . .
O2W O 0.6478(19) 1.0825(11) 0.7131(12) 0.081(4) Uani 1 1 d . . . . .
H21 H 0.6455 1.0206 0.7079 0.121 Uiso 1 1 d R U . . .
H22 H 0.5429 1.1085 0.7006 0.121 Uiso 1 1 d R U . . .
O3W O 0.7352(19) 0.0746(12) 0.8915(13) 0.090(5) Uani 1 1 d . . . . .
H31 H 0.7086 0.0788 0.8369 0.135 Uiso 1 1 d R U . . .
H32 H 0.7856 0.1116 0.9195 0.135 Uiso 1 1 d R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N3 2.057(14) . ?
Zn1 N1 2.082(13) . ?
Zn1 N4 2.186(12) . ?
Zn1 N2 2.238(15) . ?
Zn1 Br1 2.359(2) . ?
N1 C5 1.312(19) . ?
N1 C1 1.350(19) . ?
N2 C6 1.44(2) . ?
N2 C9 1.48(2) . ?
N2 C8 1.519(19) . ?
N3 C11 1.30(2) . ?
N3 C10 1.43(2) . ?
N4 C12 1.32(2) . ?
N4 C16 1.35(3) . ?
O1 C7 1.44(2) . ?
O1 C6 1.45(2) . ?
C1 C2 1.38(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.36(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.36(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.37(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.53(2) . ?
C6 H6 0.9800 . ?
C7 C8 1.52(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.49(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.47(2) . ?
C11 H11A 0.9300 . ?
C12 C13 1.38(2) . ?
C13 C14 1.43(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.36(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.40(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
Zn2 O1W 1.993(12) . ?
Zn2 Br2 2.355(3) . ?
Zn2 Br4 2.360(3) . ?
Zn2 Br3 2.384(3) . ?
O1W H11 0.8334 . ?
O1W H12 0.8522 . ?
O2W H21 0.8784 . ?
O2W H22 0.8459 . ?
O3W H31 0.8334 . ?
O3W H32 0.8812 . ?

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
N3 Zn1 N1 113.2(5) . . ?
N3 Zn1 N4 77.6(6) . . ?
N1 Zn1 N4 98.7(5) . . ?
N3 Zn1 N2 77.9(6) . . ?
N1 Zn1 N2 77.4(5) . . ?
N4 Zn1 N2 151.3(5) . . ?
N3 Zn1 Br1 125.8(4) . . ?
N1 Zn1 Br1 120.3(4) . . ?
N4 Zn1 Br1 101.5(3) . . ?
N2 Zn1 Br1 105.0(3) . . ?
C5 N1 C1 118.2(14) . . ?
C5 N1 Zn1 118.6(11) . . ?
C1 N1 Zn1 123.1(11) . . ?
C6 N2 C9 112.5(14) . . ?
C6 N2 C8 103.7(12) . . ?
C9 N2 C8 110.4(15) . . ?
C6 N2 Zn1 108.2(11) . . ?
C9 N2 Zn1 104.3(10) . . ?
C8 N2 Zn1 118.0(11) . . ?
C11 N3 C10 125.5(16) . . ?
C11 N3 Zn1 115.4(13) . . ?
C10 N3 Zn1 118.6(11) . . ?
C12 N4 C16 116.0(14) . . ?
C12 N4 Zn1 113.0(11) . . ?
C16 N4 Zn1 130.7(12) . . ?
C7 O1 C6 106.8(14) . . ?
N1 C1 C2 120.2(16) . . ?
N1 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 121.1(17) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C4 C3 C2 117.3(16) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C5 119.9(17) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 123.2(16) . . ?
N1 C5 C6 116.0(13) . . ?
C4 C5 C6 120.7(15) . . ?
N2 C6 O1 102.8(13) . . ?
N2 C6 C5 111.9(13) . . ?
O1 C6 C5 106.0(14) . . ?
N2 C6 H6 111.9 . . ?
O1 C6 H6 111.9 . . ?
C5 C6 H6 111.9 . . ?
O1 C7 C8 106.7(14) . . ?
O1 C7 H7A 110.4 . . ?
C8 C7 H7A 110.4 . . ?
O1 C7 H7B 110.4 . . ?
C8 C7 H7B 110.4 . . ?
H7A C7 H7B 108.6 . . ?
C7 C8 N2 101.9(14) . . ?
C7 C8 H8A 111.4 . . ?
N2 C8 H8A 111.4 . . ?
C7 C8 H8B 111.4 . . ?
N2 C8 H8B 111.4 . . ?
H8A C8 H8B 109.3 . . ?
N2 C9 C10 112.8(15) . . ?
N2 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
N2 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
N3 C10 C9 105.5(15) . . ?
N3 C10 H10A 110.6 . . ?
C9 C10 H10A 110.6 . . ?
N3 C10 H10B 110.6 . . ?
C9 C10 H10B 110.6 . . ?
H10A C10 H10B 108.8 . . ?
N3 C11 C12 119.4(15) . . ?
N3 C11 H11A 120.3 . . ?
C12 C11 H11A 120.3 . . ?
N4 C12 C13 127.0(15) . . ?
N4 C12 C11 114.6(13) . . ?
C13 C12 C11 118.4(15) . . ?
C12 C13 C14 114.7(16) . . ?
C12 C13 H13 122.7 . . ?
C14 C13 H13 122.7 . . ?
C15 C14 C13 121.2(17) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 117(2) . . ?
C14 C15 H15 121.3 . . ?
C16 C15 H15 121.3 . . ?
N4 C16 C15 124(2) . . ?
N4 C16 H16 118.1 . . ?
C15 C16 H16 118.1 . . ?
O1W Zn2 Br2 105.3(4) . . ?
O1W Zn2 Br4 102.8(4) . . ?
Br2 Zn2 Br4 115.51(11) . . ?
O1W Zn2 Br3 109.4(4) . . ?
Br2 Zn2 Br3 109.86(11) . . ?
Br4 Zn2 Br3 113.29(12) . . ?
Zn2 O1W H11 120.0 . . ?
Zn2 O1W H12 125.1 . . ?
H11 O1W H12 95.1 . . ?
H21 O2W H22 105.5 . . ?
H31 O3W H32 142.4 . . ?

_refine_diff_density_max         1.630
_refine_diff_density_min         -1.515
_refine_diff_density_rms         0.289

####################################################################### 
# 
# 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_3
_audit_block_doi                 10.5517/ccdc.csd.cc1zdydq
_database_code_depnum_ccdc_archive 'CCDC 1829694'
_audit_update_record             
;
2018-03-14 deposited with the CCDC.
2018-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H45 N9 O3 Zn, 2I'
_chemical_formula_sum            'C30 H45 I2 N9 O3 Zn'
_chemical_formula_weight         898.92

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           165
_space_group_name_H-M_alt        'P -3 c 1'
_space_group_name_Hall           '-P 3 2"c'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.802(3)
_cell_length_b                   13.802(2)
_cell_length_c                   20.080(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3312.7(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2655
_cell_measurement_theta_min      1.75
_cell_measurement_theta_max      26.06

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.802
_exptl_crystal_F_000             1792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    2.652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.405
_exptl_absorpt_correction_T_max  0.683
_exptl_absorpt_process_details   'W. Kabsch, Acta Cryst. D (2010)'

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.700
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Elettra Synchrotron, Trieste (Italy)'
_diffrn_radiation_monochromator  Si111
_diffrn_measurement_device_type  'Dectris Pilatus 2M'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10538
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.357
_diffrn_reflns_theta_max         27.811
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             2652
_reflns_number_gt                2411
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS - CCP4'
_computing_structure_solution    'Sir2014 (Burla, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 for Windows'
_computing_publication_material  'Wingx 2013.03 (Farrugia, 2012)'

_refine_special_details          
;
 Refined as a 2-component perfect twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0821P)²+25.5624P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0098(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2652
_refine_ls_number_parameters     150
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0638
_refine_ls_wR_factor_ref         0.1873
_refine_ls_wR_factor_gt          0.1855
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn Zn 0.6667 0.3333 0.82162(5) 0.0201(3) Uani 1 3 d S T P . .
I1 I 0.6667 0.3333 1.03878(3) 0.0295(3) Uani 1 3 d S T P . .
I2 I 0.0000 0.0000 0.88413(4) 0.0290(3) Uani 1 3 d S T P . .
N1 N 0.5099(3) 0.2513(3) 0.7687(2) 0.0216(8) Uani 1 1 d . . . . .
N2 N 0.5635(3) 0.1817(3) 0.8811(2) 0.0208(8) Uani 1 1 d D . . . .
H2A H 0.582(5) 0.195(6) 0.9293(12) 0.031 Uiso 1 1 d D U . . .
O1 O 0.2407(4) -0.0282(4) 1.0591(2) 0.0456(12) Uani 1 1 d . . . . .
H1A H 0.1751 -0.0476 1.0710 0.068 Uiso 1 1 calc R U . A 1
C1 C 0.4913(4) 0.2765(4) 0.7075(3) 0.0255(10) Uani 1 1 d . . . . .
H1 H 0.5537 0.3265 0.6812 0.031 Uiso 1 1 calc R U . . .
C2 C 0.3847(4) 0.2328(4) 0.6805(3) 0.0293(11) Uani 1 1 d . . . . .
H2 H 0.3744 0.2516 0.6366 0.035 Uiso 1 1 calc R U . . .
C3 C 0.2943(4) 0.1613(4) 0.7193(3) 0.0301(11) Uani 1 1 d . . . . .
H3 H 0.2203 0.1310 0.7027 0.036 Uiso 1 1 calc R U . . .
C4 C 0.3125(4) 0.1341(4) 0.7832(3) 0.0268(10) Uani 1 1 d . . . . .
H4 H 0.2512 0.0845 0.8104 0.032 Uiso 1 1 calc R U . . .
C5 C 0.4218(4) 0.1805(4) 0.8065(3) 0.0234(9) Uani 1 1 d . . . . .
C6 C 0.4461(4) 0.1570(4) 0.8766(3) 0.0259(10) Uani 1 1 d . . . . .
H6 H 0.4341 0.2051 0.9089 0.031 Uiso 1 1 calc R U . . .
N3 N 0.3738(4) 0.0401(4) 0.8939(2) 0.0328(10) Uani 1 1 d . . . . .
C7 C 0.4300(4) -0.0141(4) 0.8622(3) 0.0320(11) Uani 1 1 d . . . . .
H7A H 0.4036 -0.0355 0.8158 0.038 Uiso 1 1 calc R U . . .
H7B H 0.4149 -0.0822 0.8871 0.038 Uiso 1 1 calc R U . . .
C8 C 0.5570(4) 0.0735(4) 0.8634(3) 0.0280(10) Uani 1 1 d . . . . .
H8A H 0.5962 0.0531 0.8970 0.034 Uiso 1 1 calc R U . . .
H8B H 0.5912 0.0786 0.8192 0.034 Uiso 1 1 calc R U . . .
C9 C 0.3605(5) 0.0196(7) 0.9662(3) 0.0517(19) Uani 1 1 d . . . B 1
H9A H 0.3902 -0.0300 0.9786 0.062 Uiso 0.64(4) 1 calc R U P C 1
H9B H 0.4052 0.0916 0.9899 0.062 Uiso 0.64(4) 1 calc R U P C 1
C10 C 0.2458(10) -0.0308(17) 0.9876(5) 0.043(4) Uani 0.64(4) 1 d . . P B 1
H10A H 0.2037 -0.1092 0.9719 0.052 Uiso 0.64(4) 1 calc R U P C 1
H10B H 0.2110 0.0103 0.9681 0.052 Uiso 0.64(4) 1 calc R U P C 1
H9C H 0.3433 -0.0579 0.9748 0.052 Uiso 0.3635 1 d . U P C 2
H9D H 0.4315 0.0710 0.9883 0.052 Uiso 0.3635 1 d . U P C 2
C10A C 0.2740(18) 0.035(2) 0.9951(9) 0.034(6) Uani 0.36(4) 1 d . . P C 2
H10C H 0.2078 0.0045 0.9647 0.041 Uiso 0.3635 1 d . U P C 2
H10D H 0.3004 0.1145 1.0027 0.041 Uiso 0.3635 1 d . U P C 2


_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
Zn N1 2.154(4) 3_665 ?
Zn N1 2.154(4) . ?
Zn N1 2.154(4) 2_655 ?
Zn N2 2.203(4) . ?
Zn N2 2.203(4) 2_655 ?
Zn N2 2.203(4) 3_665 ?
N1 C1 1.338(7) . ?
N1 C5 1.349(6) . ?
N2 C6 1.482(6) . ?
N2 C8 1.494(6) . ?
N2 H2A 0.99(2) . ?
O1 C10 1.440(11) . ?
O1 C10A 1.490(16) . ?
O1 H1A 0.8400 . ?
C1 C2 1.390(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.381(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.520(7) . ?
C6 N3 1.453(7) . ?
C6 H6 1.0000 . ?
N3 C7 1.465(8) . ?
N3 C9 1.473(8) . ?
C7 C8 1.554(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.439(12) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10A H10C 0.9997 . ?
C10A H10D 0.9834 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Zn N1 97.77(15) 3_665 . ?
N1 Zn N1 97.77(15) 3_665 2_655 ?
N1 Zn N1 97.77(15) . 2_655 ?
N1 Zn N2 168.14(14) 3_665 . ?
N1 Zn N2 76.45(15) . . ?
N1 Zn N2 93.31(14) 2_655 . ?
N1 Zn N2 93.31(14) 3_665 2_655 ?
N1 Zn N2 168.14(14) . 2_655 ?
N1 Zn N2 76.45(15) 2_655 2_655 ?
N2 Zn N2 93.39(15) . 2_655 ?
N1 Zn N2 76.45(15) 3_665 3_665 ?
N1 Zn N2 93.31(14) . 3_665 ?
N1 Zn N2 168.14(14) 2_655 3_665 ?
N2 Zn N2 93.39(15) . 3_665 ?
N2 Zn N2 93.39(15) 2_655 3_665 ?
C1 N1 C5 118.9(4) . . ?
C1 N1 Zn 126.1(3) . . ?
C5 N1 Zn 114.1(3) . . ?
C6 N2 C8 104.0(4) . . ?
C6 N2 Zn 107.4(3) . . ?
C8 N2 Zn 120.5(3) . . ?
C6 N2 H2A 104(4) . . ?
C8 N2 H2A 108(4) . . ?
Zn N2 H2A 112(4) . . ?
C10 O1 H1A 109.5 . . ?
N1 C1 C2 123.0(5) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 118.2(5) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 119.4(5) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 119.0(5) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 121.5(5) . . ?
N1 C5 C6 117.4(4) . . ?
C4 C5 C6 121.1(4) . . ?
N3 C6 N2 107.8(4) . . ?
N3 C6 C5 110.9(4) . . ?
N2 C6 C5 109.8(4) . . ?
N3 C6 H6 109.4 . . ?
N2 C6 H6 109.4 . . ?
C5 C6 H6 109.4 . . ?
C6 N3 C7 102.6(4) . . ?
C6 N3 C9 113.5(5) . . ?
C7 N3 C9 112.2(5) . . ?
N3 C7 C8 106.0(4) . . ?
N3 C7 H7A 110.5 . . ?
C8 C7 H7A 110.5 . . ?
N3 C7 H7B 110.5 . . ?
C8 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
N2 C8 C7 105.2(4) . . ?
N2 C8 H8A 110.7 . . ?
C7 C8 H8A 110.7 . . ?
N2 C8 H8B 110.7 . . ?
C7 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C10 C9 N3 112.9(6) . . ?
C10 C9 H9A 109.0 . . ?
N3 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
N3 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 O1 110.0(8) . . ?
C9 C10 H10A 109.7 . . ?
O1 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
O1 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
O1 C10A H10C 109.4 . . ?
O1 C10A H10D 110.6 . . ?
H10C C10A H10D 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -0.1(7) . . . . ?
Zn N1 C1 C2 -169.2(3) . . . . ?
N1 C1 C2 C3 0.9(7) . . . . ?
C1 C2 C3 C4 -1.1(7) . . . . ?
C2 C3 C4 C5 0.6(7) . . . . ?
C1 N1 C5 C4 -0.4(7) . . . . ?
Zn N1 C5 C4 169.9(4) . . . . ?
C1 N1 C5 C6 -178.0(4) . . . . ?
Zn N1 C5 C6 -7.6(5) . . . . ?
C3 C4 C5 N1 0.2(7) . . . . ?
C3 C4 C5 C6 177.7(4) . . . . ?
C8 N2 C6 N3 30.8(5) . . . . ?
Zn N2 C6 N3 159.7(3) . . . . ?
C8 N2 C6 C5 -90.1(5) . . . . ?
Zn N2 C6 C5 38.8(4) . . . . ?
N1 C5 C6 N3 -141.0(4) . . . . ?
C4 C5 C6 N3 41.5(6) . . . . ?
N1 C5 C6 N2 -21.9(6) . . . . ?
C4 C5 C6 N2 160.5(4) . . . . ?
N2 C6 N3 C7 -39.2(5) . . . . ?
C5 C6 N3 C7 81.0(5) . . . . ?
N2 C6 N3 C9 82.1(5) . . . . ?
C5 C6 N3 C9 -157.7(5) . . . . ?
C6 N3 C7 C8 31.3(5) . . . . ?
C9 N3 C7 C8 -90.9(5) . . . . ?
C6 N2 C8 C7 -10.1(5) . . . . ?
Zn N2 C8 C7 -130.4(4) . . . . ?
N3 C7 C8 N2 -13.1(6) . . . . ?
C6 N3 C9 C10 120.7(11) . . . . ?
C7 N3 C9 C10 -123.5(11) . . . . ?
N3 C9 C10 O1 -168.6(10) . . . . ?

_refine_diff_density_max         2.563
_refine_diff_density_min         -3.031
_refine_diff_density_rms         0.235

