# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1413160'
_audit_update_record             
;
2015-07-16 deposited with the CCDC.
2015-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H12 Cl2 N4 O4 Zn'
_chemical_formula_sum            'C24 H12 Cl2 N4 O4 Zn'
_chemical_formula_weight         556.65

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 '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                   11.913(2)
_cell_length_b                   12.215(2)
_cell_length_c                   13.877(3)
_cell_angle_alpha                108.44(3)
_cell_angle_beta                 93.66(3)
_cell_angle_gamma                111.61(3)
_cell_volume                     1743.4(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4901
_cell_measurement_theta_min      3.0427
_cell_measurement_theta_max      27.4971

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.060
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.884
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8145
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Saturn724 (2x2 bin mode)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14628
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.041
_diffrn_reflns_theta_max         27.524
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             7681
_reflns_number_gt                6540
_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.
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.131 0.000 0.437 822 133 ' '
_platon_squeeze_details          
;
SQUEEZE removed 2.5 disordered NMP  molecules per formula unit. 
This value calculated based upon volume/count_electrons analysis and TG-MS analysis.
;

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0881P)²+1.1598P] 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         7681
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1525
_refine_ls_wR_factor_gt          0.1450
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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 0.83826(3) 0.64628(3) 0.19885(3) 0.03357(12) Uani 1 1 d . . . . .
Cl1 Cl 0.87565(8) 0.82968(8) 0.32287(6) 0.0510(2) Uani 1 1 d . . . . .
Cl2 Cl 0.87249(7) 0.63068(8) 0.03964(6) 0.04296(18) Uani 1 1 d . . . . .
O1 O 0.33001(18) 0.2010(2) -0.07492(17) 0.0435(5) Uani 1 1 d . . . . .
O2 O 0.2686(2) 0.2918(2) 0.25398(18) 0.0532(6) Uani 1 1 d . . . . .
O3 O 1.36451(19) 0.6631(2) 0.32283(19) 0.0488(6) Uani 1 1 d . . . . .
O4 O 1.11401(17) 0.3669(2) 0.43556(16) 0.0412(5) Uani 1 1 d . . . . .
N1 N 0.6586(2) 0.5247(2) 0.1817(2) 0.0360(5) Uani 1 1 d . . . . .
N2 N 0.29444(19) 0.2499(2) 0.08866(19) 0.0328(5) Uani 1 1 d . . . . .
N3 N 0.9461(2) 0.5710(3) 0.2535(2) 0.0395(6) Uani 1 1 d . . . . .
N4 N 1.2402(2) 0.5169(2) 0.38218(18) 0.0328(5) Uani 1 1 d . . . . .
C1 C 0.5683(2) 0.5477(2) 0.1418(2) 0.0331(6) Uani 1 1 d . . . . .
H1 H 0.5879 0.6245 0.1331 0.040 Uiso 1 1 calc R U . . .
C2 C 0.4466(2) 0.4604(3) 0.1131(2) 0.0327(6) Uani 1 1 d . . . . .
H2 H 0.3849 0.4785 0.0862 0.039 Uiso 1 1 calc R U . . .
C3 C 0.4187(2) 0.3468(3) 0.1251(2) 0.0359(6) Uani 1 1 d . . . . .
C4 C 0.5091(3) 0.3279(3) 0.1757(3) 0.0574(10) Uani 1 1 d . . . . .
H4 H 0.4906 0.2548 0.1905 0.069 Uiso 1 1 calc R U . . .
C5 C 0.6276(3) 0.4200(3) 0.2036(3) 0.0548(9) Uani 1 1 d . . . . .
H5 H 0.6887 0.4087 0.2394 0.066 Uiso 1 1 calc R U . . .
C6 C 0.2263(3) 0.2275(3) 0.1634(2) 0.0373(6) Uani 1 1 d . . . . .
C7 C 0.1005(2) 0.1232(3) 0.1242(2) 0.0358(6) Uani 1 1 d . . . . .
C8 C 0.0596(2) 0.0494(2) 0.0177(2) 0.0298(5) Uani 1 1 d . . . . .
C9 C 0.1344(2) 0.0729(3) -0.0540(2) 0.0342(6) Uani 1 1 d . . . . .
C10 C 0.2596(2) 0.1769(3) -0.0178(2) 0.0344(6) Uani 1 1 d . . . . .
C11 C 0.0926(3) 0.0006(3) -0.1576(3) 0.0467(7) Uani 1 1 d . . . . .
H11 H 0.1429 0.0171 -0.2044 0.056 Uiso 1 1 calc R U . . .
C12 C 0.0262(3) 0.0986(3) 0.1936(3) 0.0472(7) Uani 1 1 d . . . . .
H12 H 0.0544 0.1473 0.2640 0.057 Uiso 1 1 calc R U . . .
C13 C 1.0039(3) 0.5100(3) 0.1924(2) 0.0392(6) Uani 1 1 d . . . . .
H13 H 0.9786 0.4820 0.1208 0.047 Uiso 1 1 calc R U . . .
C14 C 1.0988(3) 0.4873(3) 0.2310(2) 0.0395(6) Uani 1 1 d . . . . .
H14 H 1.1379 0.4456 0.1868 0.047 Uiso 1 1 calc R U . . .
C15 C 1.1343(2) 0.5278(3) 0.3370(2) 0.0360(6) Uani 1 1 d . . . . .
C16 C 1.0708(3) 0.5827(4) 0.4006(2) 0.0477(8) Uani 1 1 d . . . . .
H16 H 1.0901 0.6050 0.4721 0.057 Uiso 1 1 calc R U . . .
C17 C 0.9784(3) 0.6038(4) 0.3562(3) 0.0498(8) Uani 1 1 d . . . . .
H17 H 0.9363 0.6425 0.3993 0.060 Uiso 1 1 calc R U . . .
C18 C 1.2188(2) 0.4316(3) 0.4335(2) 0.0347(6) Uani 1 1 d . . . . .
C19 C 1.3292(2) 0.4257(3) 0.4833(2) 0.0319(5) Uani 1 1 d . . . . .
C20 C 1.4478(2) 0.5030(3) 0.4764(2) 0.0299(5) Uani 1 1 d . . . . .
C21 C 1.4649(2) 0.5867(3) 0.4217(2) 0.0327(6) Uani 1 1 d . . . . .
C22 C 1.3560(3) 0.5934(3) 0.3707(2) 0.0354(6) Uani 1 1 d . . . . .
C23 C 1.5811(3) 0.6610(3) 0.4161(2) 0.0367(6) Uani 1 1 d . . . . .
H23 H 1.5912 0.7152 0.3799 0.044 Uiso 1 1 calc R U . . .
C24 C 1.3148(2) 0.3441(3) 0.5352(2) 0.0368(6) Uani 1 1 d . . . . .
H24 H 1.2362 0.2923 0.5382 0.044 Uiso 1 1 calc 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 N1 2.052(2) . ?
Zn1 N3 2.064(2) . ?
Zn1 Cl1 2.2152(13) . ?
Zn1 Cl2 2.2338(10) . ?
O1 C10 1.212(3) . ?
O2 C6 1.206(4) . ?
O3 C22 1.215(3) . ?
O4 C18 1.215(3) . ?
N1 C5 1.333(4) . ?
N1 C1 1.337(3) . ?
N2 C6 1.391(4) . ?
N2 C10 1.402(4) . ?
N2 C3 1.443(3) . ?
N3 C17 1.340(4) . ?
N3 C13 1.342(4) . ?
N4 C18 1.399(3) . ?
N4 C22 1.405(4) . ?
N4 C15 1.442(3) . ?
C1 C2 1.385(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.370(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(4) . ?
C4 C5 1.376(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.488(4) . ?
C7 C12 1.377(4) . ?
C7 C8 1.406(4) . ?
C8 C9 1.403(4) . ?
C8 C8 1.411(5) 2 ?
C9 C11 1.369(4) . ?
C9 C10 1.482(4) . ?
C11 C12 1.409(4) 2 ?
C11 H11 0.9300 . ?
C12 C11 1.409(4) 2 ?
C12 H12 0.9300 . ?
C13 C14 1.377(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(4) . ?
C16 C17 1.372(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.482(3) . ?
C19 C24 1.373(4) . ?
C19 C20 1.410(4) . ?
C20 C20 1.405(5) 2_866 ?
C20 C21 1.421(4) . ?
C21 C23 1.371(4) . ?
C21 C22 1.480(3) . ?
C23 C24 1.405(4) 2_866 ?
C23 H23 0.9300 . ?
C24 C23 1.405(4) 2_866 ?
C24 H24 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Zn1 N3 106.11(10) . . ?
N1 Zn1 Cl1 108.77(9) . . ?
N3 Zn1 Cl1 106.40(9) . . ?
N1 Zn1 Cl2 106.97(9) . . ?
N3 Zn1 Cl2 104.89(8) . . ?
Cl1 Zn1 Cl2 122.59(4) . . ?
C5 N1 C1 118.2(2) . . ?
C5 N1 Zn1 123.01(19) . . ?
C1 N1 Zn1 118.73(18) . . ?
C6 N2 C10 125.9(2) . . ?
C6 N2 C3 117.1(2) . . ?
C10 N2 C3 116.5(2) . . ?
C17 N3 C13 117.8(2) . . ?
C17 N3 Zn1 118.8(2) . . ?
C13 N3 Zn1 122.25(19) . . ?
C18 N4 C22 125.9(2) . . ?
C18 N4 C15 117.4(2) . . ?
C22 N4 C15 116.8(2) . . ?
N1 C1 C2 121.9(2) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 N2 120.2(2) . . ?
C4 C3 N2 120.4(2) . . ?
C5 C4 C3 118.2(3) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
N1 C5 C4 122.8(3) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
O2 C6 N2 120.3(3) . . ?
O2 C6 C7 123.5(3) . . ?
N2 C6 C7 116.1(3) . . ?
C12 C7 C8 120.7(3) . . ?
C12 C7 C6 119.3(3) . . ?
C8 C7 C6 120.0(3) . . ?
C9 C8 C7 121.4(2) . . ?
C9 C8 C8 119.5(3) . 2 ?
C7 C8 C8 119.0(3) . 2 ?
C11 C9 C8 120.6(3) . . ?
C11 C9 C10 119.5(3) . . ?
C8 C9 C10 120.0(3) . . ?
O1 C10 N2 120.1(2) . . ?
O1 C10 C9 123.6(3) . . ?
N2 C10 C9 116.3(2) . . ?
C9 C11 C12 120.4(3) . 2 ?
C9 C11 H11 119.8 . . ?
C12 C11 H11 119.8 2 . ?
C7 C12 C11 119.8(3) . 2 ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 2 . ?
N3 C13 C14 122.8(3) . . ?
N3 C13 H13 118.6 . . ?
C14 C13 H13 118.6 . . ?
C15 C14 C13 118.1(3) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C16 C15 C14 119.9(3) . . ?
C16 C15 N4 119.5(3) . . ?
C14 C15 N4 120.6(2) . . ?
C17 C16 C15 118.4(3) . . ?
C17 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
N3 C17 C16 122.8(3) . . ?
N3 C17 H17 118.6 . . ?
C16 C17 H17 118.6 . . ?
O4 C18 N4 120.1(2) . . ?
O4 C18 C19 123.4(3) . . ?
N4 C18 C19 116.5(2) . . ?
C24 C19 C20 120.6(2) . . ?
C24 C19 C18 119.5(2) . . ?
C20 C19 C18 119.9(2) . . ?
C20 C20 C19 119.6(3) 2_866 . ?
C20 C20 C21 118.7(3) 2_866 . ?
C19 C20 C21 121.6(2) . . ?
C23 C21 C20 120.6(2) . . ?
C23 C21 C22 120.0(2) . . ?
C20 C21 C22 119.4(2) . . ?
O3 C22 N4 120.8(2) . . ?
O3 C22 C21 122.6(3) . . ?
N4 C22 C21 116.6(2) . . ?
C21 C23 C24 120.4(3) . 2_866 ?
C21 C23 H23 119.8 . . ?
C24 C23 H23 119.8 2_866 . ?
C19 C24 C23 120.0(3) . 2_866 ?
C19 C24 H24 120.0 . . ?
C23 C24 H24 120.0 2_866 . ?

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 -6.9(5) . . . . ?
Zn1 N1 C1 C2 169.9(2) . . . . ?
N1 C1 C2 C3 -0.7(5) . . . . ?
C1 C2 C3 C4 7.2(5) . . . . ?
C1 C2 C3 N2 -175.2(3) . . . . ?
C6 N2 C3 C2 -107.4(3) . . . . ?
C10 N2 C3 C2 80.3(3) . . . . ?
C6 N2 C3 C4 70.1(4) . . . . ?
C10 N2 C3 C4 -102.2(4) . . . . ?
C2 C3 C4 C5 -6.1(6) . . . . ?
N2 C3 C4 C5 176.3(3) . . . . ?
C1 N1 C5 C4 8.1(6) . . . . ?
Zn1 N1 C5 C4 -168.5(3) . . . . ?
C3 C4 C5 N1 -1.6(7) . . . . ?
C10 N2 C6 O2 175.3(3) . . . . ?
C3 N2 C6 O2 3.8(4) . . . . ?
C10 N2 C6 C7 -5.8(4) . . . . ?
C3 N2 C6 C7 -177.3(2) . . . . ?
O2 C6 C7 C12 1.0(5) . . . . ?
N2 C6 C7 C12 -177.8(3) . . . . ?
O2 C6 C7 C8 -177.6(3) . . . . ?
N2 C6 C7 C8 3.6(4) . . . . ?
C12 C7 C8 C9 -179.7(3) . . . . ?
C6 C7 C8 C9 -1.1(4) . . . . ?
C12 C7 C8 C8 1.0(5) . . . 2 ?
C6 C7 C8 C8 179.6(3) . . . 2 ?
C7 C8 C9 C11 -179.5(3) . . . . ?
C8 C8 C9 C11 -0.2(5) 2 . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C8 C8 C9 C10 179.7(3) 2 . . . ?
C6 N2 C10 O1 -175.4(3) . . . . ?
C3 N2 C10 O1 -3.9(4) . . . . ?
C6 N2 C10 C9 5.2(4) . . . . ?
C3 N2 C10 C9 176.7(2) . . . . ?
C11 C9 C10 O1 -1.7(4) . . . . ?
C8 C9 C10 O1 178.5(3) . . . . ?
C11 C9 C10 N2 177.7(3) . . . . ?
C8 C9 C10 N2 -2.2(4) . . . . ?
C8 C9 C11 C12 -0.1(5) . . . 2 ?
C10 C9 C11 C12 -179.9(3) . . . 2 ?
C8 C7 C12 C11 -0.8(5) . . . 2 ?
C6 C7 C12 C11 -179.4(3) . . . 2 ?
C17 N3 C13 C14 -4.0(5) . . . . ?
Zn1 N3 C13 C14 163.3(2) . . . . ?
N3 C13 C14 C15 0.8(5) . . . . ?
C13 C14 C15 C16 3.7(5) . . . . ?
C13 C14 C15 N4 -174.4(3) . . . . ?
C18 N4 C15 C16 69.5(4) . . . . ?
C22 N4 C15 C16 -110.4(3) . . . . ?
C18 N4 C15 C14 -112.4(3) . . . . ?
C22 N4 C15 C14 67.7(4) . . . . ?
C14 C15 C16 C17 -4.6(5) . . . . ?
N4 C15 C16 C17 173.5(3) . . . . ?
C13 N3 C17 C16 3.0(5) . . . . ?
Zn1 N3 C17 C16 -164.8(3) . . . . ?
C15 C16 C17 N3 1.3(6) . . . . ?
C22 N4 C18 O4 -177.4(3) . . . . ?
C15 N4 C18 O4 2.7(4) . . . . ?
C22 N4 C18 C19 2.4(4) . . . . ?
C15 N4 C18 C19 -177.5(2) . . . . ?
O4 C18 C19 C24 -0.3(4) . . . . ?
N4 C18 C19 C24 179.8(3) . . . . ?
O4 C18 C19 C20 179.3(3) . . . . ?
N4 C18 C19 C20 -0.6(4) . . . . ?
C24 C19 C20 C20 -0.4(5) . . . 2_866 ?
C18 C19 C20 C20 -180.0(3) . . . 2_866 ?
C24 C19 C20 C21 179.0(3) . . . . ?
C18 C19 C20 C21 -0.6(4) . . . . ?
C20 C20 C21 C23 -0.7(5) 2_866 . . . ?
C19 C20 C21 C23 179.9(3) . . . . ?
C20 C20 C21 C22 179.5(3) 2_866 . . . ?
C19 C20 C21 C22 0.1(4) . . . . ?
C18 N4 C22 O3 178.7(3) . . . . ?
C15 N4 C22 O3 -1.4(4) . . . . ?
C18 N4 C22 C21 -2.9(4) . . . . ?
C15 N4 C22 C21 177.0(2) . . . . ?
C23 C21 C22 O3 0.1(5) . . . . ?
C20 C21 C22 O3 180.0(3) . . . . ?
C23 C21 C22 N4 -178.3(3) . . . . ?
C20 C21 C22 N4 1.5(4) . . . . ?
C20 C21 C23 C24 -0.2(4) . . . 2_866 ?
C22 C21 C23 C24 179.6(3) . . . 2_866 ?
C20 C19 C24 C23 1.3(4) . . . 2_866 ?
C18 C19 C24 C23 -179.1(3) . . . 2_866 ?

_refine_diff_density_max         0.516
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.082

_shelxl_version_number           2014/6


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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1413161'
_audit_update_record             
;
2015-07-16 deposited with the CCDC.
2015-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H12 Br2 N4 O4 Zn'
_chemical_formula_sum            'C24 H12 Br2 N4 O4 Zn'
_chemical_formula_weight         645.57

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                   12.002(2)
_cell_length_b                   12.170(2)
_cell_length_c                   14.130(3)
_cell_angle_alpha                108.73(3)
_cell_angle_beta                 93.80(3)
_cell_angle_gamma                112.58(3)
_cell_volume                     1761.7(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6014
_cell_measurement_theta_min      3.4514
_cell_measurement_theta_max      27.5398

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    2.992
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7691
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Saturn724 (2x2 bin mode)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14866
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_av_R_equivalents  0.0385
_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       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.414
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             7780
_reflns_number_gt                6148
_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.
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 1.000 0.074 807 139 ' '
_platon_squeeze_details          
;
SQUEEZE removed 2.5 disordered NMP  molecules per formula unit. 
This value calculated based upon volume/count_electrons analysis and TG-MS analysis.
;


_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1423P)²+1.9455P] 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         7780
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0696
_refine_ls_wR_factor_ref         0.2181
_refine_ls_wR_factor_gt          0.2045
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.15343(4) 0.34713(5) 0.29390(4) 0.02946(18) Uani 1 1 d . . . . .
Br1 Br 0.11936(5) 0.36450(6) 0.46058(4) 0.04097(18) Uani 1 1 d . . . . .
Br2 Br 0.11385(8) 0.14766(7) 0.16876(6) 0.0683(3) Uani 1 1 d . . . . .
N1 N 0.0495(4) 0.4250(4) 0.2398(3) 0.0350(9) Uani 1 1 d . . . . .
N2 N -0.2441(3) 0.4772(4) 0.1114(3) 0.0291(8) Uani 1 1 d . . . . .
N3 N 0.3345(4) 0.4694(4) 0.3118(3) 0.0317(8) Uani 1 1 d . . . . .
N4 N 0.7028(3) 0.7483(4) 0.4095(3) 0.0261(8) Uani 1 1 d . . . . .
C1 C 0.0161(5) 0.3904(6) 0.1382(4) 0.0428(13) Uani 1 1 d . . . . .
H1 H 0.0564 0.3500 0.0960 0.051 Uiso 1 1 calc R U . . .
C2 C -0.0742(5) 0.4116(6) 0.0937(4) 0.0394(12) Uani 1 1 d . . . . .
H2 H -0.0924 0.3898 0.0233 0.047 Uiso 1 1 calc R U . . .
C3 C -0.1377(4) 0.4662(5) 0.1559(4) 0.0329(10) Uani 1 1 d . . . . .
C4 C -0.1038(5) 0.5069(6) 0.2610(4) 0.0377(11) Uani 1 1 d . . . . .
H4 H -0.1434 0.5471 0.3043 0.045 Uiso 1 1 calc R U . . .
C5 C -0.0077(5) 0.4850(5) 0.2992(4) 0.0382(11) Uani 1 1 d . . . . .
H5 H 0.0179 0.5137 0.3698 0.046 Uiso 1 1 calc R U . . .
C6 C -0.3592(4) 0.4037(5) 0.1245(4) 0.0324(10) Uani 1 1 d . . . . .
C7 C -0.4665(4) 0.4130(5) 0.0762(3) 0.0293(9) Uani 1 1 d . . . . .
C8 C -0.4484(4) 0.4948(4) 0.0222(3) 0.0263(9) Uani 1 1 d . . . . .
C9 C -0.3293(4) 0.5724(5) 0.0149(3) 0.0271(9) Uani 1 1 d . . . . .
C10 C -0.2196(4) 0.5649(5) 0.0627(4) 0.0300(10) Uani 1 1 d . . . . .
C11 C -0.3131(4) 0.6556(5) -0.0353(4) 0.0319(10) Uani 1 1 d . . . . .
H11 H -0.2341 0.7073 -0.0386 0.038 Uiso 1 1 calc R U . . .
C12 C -0.5835(4) 0.3380(5) 0.0814(4) 0.0318(10) Uani 1 1 d . . . . .
H12 H -0.5945 0.2823 0.1158 0.038 Uiso 1 1 calc R U . . .
C13 C 0.4227(4) 0.4467(4) 0.3550(4) 0.0303(10) Uani 1 1 d . . . . .
H13 H 0.4004 0.3700 0.3652 0.036 Uiso 1 1 calc R U . . .
C14 C 0.5458(4) 0.5351(5) 0.3846(4) 0.0315(10) Uani 1 1 d . . . . .
H14 H 0.6061 0.5178 0.4133 0.038 Uiso 1 1 calc R U . . .
C15 C 0.5761(4) 0.6476(4) 0.3707(4) 0.0292(9) Uani 1 1 d . . . . .
C16 C 0.4898(5) 0.6671(5) 0.3189(5) 0.0408(12) Uani 1 1 d . . . . .
H16 H 0.5120 0.7402 0.3032 0.049 Uiso 1 1 calc R U . . .
C17 C 0.3680(5) 0.5746(5) 0.2903(5) 0.0424(13) Uani 1 1 d . . . . .
H17 H 0.3083 0.5868 0.2551 0.051 Uiso 1 1 calc R U . . .
C18 C 0.7351(4) 0.8248(4) 0.5122(4) 0.0284(9) Uani 1 1 d . . . . .
C19 C 0.8615(4) 0.9311(4) 0.5507(4) 0.0283(9) Uani 1 1 d . . . . .
C20 C 0.9411(4) 0.9507(4) 0.4817(3) 0.0247(9) Uani 1 1 d . . . . .
C21 C 0.9008(4) 0.8694(5) 0.3773(4) 0.0310(10) Uani 1 1 d . . . . .
C22 C 0.7754(4) 0.7651(5) 0.3370(4) 0.0323(10) Uani 1 1 d . . . . .
C23 C 0.9793(5) 0.8905(5) 0.3119(4) 0.0381(12) Uani 1 1 d . . . . .
H23 H 0.9523 0.8386 0.2426 0.046 Uiso 1 1 calc R U . . .
C24 C 0.9012(5) 1.0113(5) 0.6521(4) 0.0376(11) Uani 1 1 d . . . . .
H24 H 0.8482 0.9999 0.6968 0.045 Uiso 1 1 calc R U . . .
O1 O -0.1152(3) 0.6313(4) 0.0627(3) 0.0365(8) Uani 1 1 d . . . . .
O2 O -0.3682(3) 0.3355(4) 0.1736(3) 0.0438(9) Uani 1 1 d . . . . .
O3 O 0.7327(3) 0.6958(4) 0.2480(3) 0.0434(9) Uani 1 1 d . . . . .
O4 O 0.6619(3) 0.8023(3) 0.5674(3) 0.0369(8) 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 2.050(4) . ?
Zn1 N1 2.070(4) . ?
Zn1 Br2 2.3434(14) . ?
Zn1 Br1 2.3734(9) . ?
N1 C5 1.332(7) . ?
N1 C1 1.344(7) . ?
N2 C6 1.391(6) . ?
N2 C10 1.399(6) . ?
N2 C3 1.456(5) . ?
N3 C17 1.328(6) . ?
N3 C13 1.348(6) . ?
N4 C18 1.379(6) . ?
N4 C22 1.402(6) . ?
N4 C15 1.464(6) . ?
C1 C2 1.365(7) . ?
C2 C3 1.377(7) . ?
C3 C4 1.382(7) . ?
C4 C5 1.393(6) . ?
C6 O2 1.223(6) . ?
C6 C7 1.477(6) . ?
C7 C12 1.373(7) . ?
C7 C8 1.402(6) . ?
C8 C9 1.410(6) . ?
C8 C8 1.418(8) 2_465 ?
C9 C11 1.375(6) . ?
C9 C10 1.488(6) . ?
C10 O1 1.202(6) . ?
C11 C12 1.403(6) 2_465 ?
C12 C11 1.403(6) 2_465 ?
C13 C14 1.387(6) . ?
C14 C15 1.358(6) . ?
C15 C16 1.365(6) . ?
C16 C17 1.390(7) . ?
C18 O4 1.224(6) . ?
C18 C19 1.484(6) . ?
C19 C24 1.374(7) . ?
C19 C20 1.420(6) . ?
C20 C20 1.382(8) 2_776 ?
C20 C21 1.411(7) . ?
C21 C23 1.375(7) . ?
C21 C22 1.468(6) . ?
C22 O3 1.207(6) . ?
C23 C24 1.393(7) 2_776 ?
C24 C23 1.393(7) 2_776 ?

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 105.74(16) . . ?
N3 Zn1 Br2 108.06(13) . . ?
N1 Zn1 Br2 108.95(13) . . ?
N3 Zn1 Br1 106.69(13) . . ?
N1 Zn1 Br1 105.70(12) . . ?
Br2 Zn1 Br1 120.75(4) . . ?
C5 N1 C1 117.6(4) . . ?
C5 N1 Zn1 122.1(3) . . ?
C1 N1 Zn1 118.7(3) . . ?
C6 N2 C10 126.1(4) . . ?
C6 N2 C3 117.4(4) . . ?
C10 N2 C3 116.4(4) . . ?
C17 N3 C13 118.9(4) . . ?
C17 N3 Zn1 123.0(3) . . ?
C13 N3 Zn1 117.9(3) . . ?
C18 N4 C22 126.4(4) . . ?
C18 N4 C15 116.6(4) . . ?
C22 N4 C15 116.8(4) . . ?
N1 C1 C2 123.3(5) . . ?
C1 C2 C3 118.3(5) . . ?
C2 C3 C4 120.2(4) . . ?
C2 C3 N2 120.4(4) . . ?
C4 C3 N2 119.4(4) . . ?
C3 C4 C5 117.1(5) . . ?
N1 C5 C4 123.4(5) . . ?
O2 C6 N2 120.2(4) . . ?
O2 C6 C7 123.1(4) . . ?
N2 C6 C7 116.6(4) . . ?
C12 C7 C8 120.5(4) . . ?
C12 C7 C6 119.7(4) . . ?
C8 C7 C6 119.7(4) . . ?
C7 C8 C9 121.8(4) . . ?
C7 C8 C8 119.3(5) . 2_465 ?
C9 C8 C8 118.8(5) . 2_465 ?
C11 C9 C8 120.9(4) . . ?
C11 C9 C10 119.5(4) . . ?
C8 C9 C10 119.6(4) . . ?
O1 C10 N2 120.8(4) . . ?
O1 C10 C9 123.2(4) . . ?
N2 C10 C9 115.9(4) . . ?
C9 C11 C12 119.7(4) . 2_465 ?
C7 C12 C11 120.7(4) . 2_465 ?
N3 C13 C14 121.6(4) . . ?
C15 C14 C13 118.3(4) . . ?
C14 C15 C16 120.6(4) . . ?
C14 C15 N4 120.1(4) . . ?
C16 C15 N4 119.3(4) . . ?
C15 C16 C17 118.1(5) . . ?
N3 C17 C16 121.9(5) . . ?
O4 C18 N4 120.2(4) . . ?
O4 C18 C19 123.0(4) . . ?
N4 C18 C19 116.8(4) . . ?
C24 C19 C20 120.0(4) . . ?
C24 C19 C18 120.4(4) . . ?
C20 C19 C18 119.6(4) . . ?
C20 C20 C21 120.4(5) 2_776 . ?
C20 C20 C19 119.2(5) 2_776 . ?
C21 C20 C19 120.4(4) . . ?
C23 C21 C20 119.3(4) . . ?
C23 C21 C22 119.6(4) . . ?
C20 C21 C22 121.1(4) . . ?
O3 C22 N4 119.5(4) . . ?
O3 C22 C21 124.7(5) . . ?
N4 C22 C21 115.7(4) . . ?
C21 C23 C24 120.9(5) . 2_776 ?
C19 C24 C23 120.1(4) . 2_776 ?

_refine_diff_density_max         1.769
_refine_diff_density_min         -1.951
_refine_diff_density_rms         0.143

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1413162'
_audit_update_record             
;
2015-07-16 deposited with the CCDC.
2015-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H12 I2 N4 O4 Zn'
_chemical_formula_sum            'C24 H12 I2 N4 O4 Zn'
_chemical_formula_weight         739.55

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      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                   11.893(2)
_cell_length_b                   12.193(2)
_cell_length_c                   14.724(3)
_cell_angle_alpha                110.32(3)
_cell_angle_beta                 93.68(3)
_cell_angle_gamma                112.89(3)
_cell_volume                     1794.8(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    11609
_cell_measurement_theta_min      3.0725
_cell_measurement_theta_max      27.4872

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    2.431
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4833
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Saturn724 (2x2 bin mode)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17645
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_av_R_equivalents  0.0562
_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       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.073
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             8121
_reflns_number_gt                5343
_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.
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 1.000 0.361 776 143 ' '
_platon_squeeze_details          
;
SQUEEZE removed 2.5 disordered NMP  molecules per formula unit. 
This value calculated based upon volume/count_electrons analysis and TG-MS analysis.
;

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-2014/6 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0833P)²] 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         8121
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1752
_refine_ls_wR_factor_gt          0.1585
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.13958(5) 0.32402(6) 0.28352(5) 0.04512(18) Uani 1 1 d . . . . .
I1 I 0.10089(4) 0.34842(5) 0.45819(3) 0.06444(16) Uani 1 1 d . . . . .
I2 I 0.11418(5) 0.10916(4) 0.15418(3) 0.06919(17) Uani 1 1 d . . . . .
N1 N 0.3209(4) 0.4577(5) 0.3097(3) 0.0462(10) Uani 1 1 d . . . . .
N2 N 0.6927(4) 0.7519(4) 0.4073(3) 0.0451(10) Uani 1 1 d . . . . .
N3 N 0.0276(4) 0.3902(5) 0.2261(3) 0.0499(11) Uani 1 1 d . . . . .
N4 N -0.2522(4) 0.4612(5) 0.1044(3) 0.0451(10) Uani 1 1 d . . . . .
O1 O 0.6543(4) 0.8116(4) 0.5610(3) 0.0676(12) Uani 1 1 d . . . . .
O2 O 0.7295(4) 0.6811(4) 0.2542(3) 0.0693(13) Uani 1 1 d . . . . .
O3 O -0.3850(4) 0.3249(5) 0.1613(4) 0.0795(15) Uani 1 1 d . . . . .
O4 O -0.1107(4) 0.6198(4) 0.0653(3) 0.0597(11) Uani 1 1 d . . . . .
C1 C 0.3537(6) 0.5653(7) 0.2923(6) 0.075(2) Uani 1 1 d . . . . .
H1 H 0.2912 0.5753 0.2595 0.090 Uiso 1 1 calc R U . . .
C2 C 0.4759(6) 0.6632(7) 0.3204(6) 0.074(2) Uani 1 1 d . . . . .
H2 H 0.4953 0.7363 0.3063 0.089 Uiso 1 1 calc R U . . .
C3 C 0.5656(5) 0.6477(5) 0.3692(4) 0.0437(12) Uani 1 1 d . . . . .
C4 C 0.5363(5) 0.5348(6) 0.3816(5) 0.0571(15) Uani 1 1 d . . . . .
H4 H 0.5983 0.5206 0.4106 0.068 Uiso 1 1 calc R U . . .
C5 C 0.4153(5) 0.4439(6) 0.3509(5) 0.0586(15) Uani 1 1 d . . . . .
H5 H 0.3967 0.3668 0.3589 0.070 Uiso 1 1 calc R U . . .
C6 C 0.7270(5) 0.8319(5) 0.5085(4) 0.0467(12) Uani 1 1 d . . . . .
C7 C 0.8572(5) 0.9381(5) 0.5460(4) 0.0439(12) Uani 1 1 d . . . . .
C8 C 0.8991(5) 1.0259(6) 0.6465(4) 0.0513(14) Uani 1 1 d . . . . .
H8 H 0.8451 1.0179 0.6893 0.062 Uiso 1 1 calc R U . . .
C9 C 0.9379(5) 0.9511(5) 0.4817(4) 0.0390(10) Uani 1 1 d . . . . .
C10 C 0.8985(5) 0.8643(5) 0.3800(4) 0.0418(11) Uani 1 1 d . . . . .
C11 C 0.9824(5) 0.8782(6) 0.3188(4) 0.0541(15) Uani 1 1 d . . . . .
H11 H 0.9564 0.8201 0.2523 0.065 Uiso 1 1 calc R U . . .
C12 C 0.7697(5) 0.7619(5) 0.3412(4) 0.0454(12) Uani 1 1 d . . . . .
C13 C -0.0269(6) 0.4571(6) 0.2849(4) 0.0578(15) Uani 1 1 d . . . . .
H13 H -0.0042 0.4840 0.3535 0.069 Uiso 1 1 calc R U . . .
C14 C -0.1133(6) 0.4861(6) 0.2473(4) 0.0567(15) Uani 1 1 d . . . . .
H14 H -0.1474 0.5344 0.2897 0.068 Uiso 1 1 calc R U . . .
C15 C -0.1498(5) 0.4442(6) 0.1473(4) 0.0470(12) Uani 1 1 d . . . . .
C16 C -0.0902(6) 0.3859(8) 0.0886(4) 0.0686(19) Uani 1 1 d . . . . .
H16 H -0.1076 0.3645 0.0206 0.082 Uiso 1 1 calc R U . . .
C17 C -0.0033(6) 0.3578(8) 0.1297(5) 0.0653(18) Uani 1 1 d . . . . .
H17 H 0.0351 0.3144 0.0879 0.078 Uiso 1 1 calc R U . . .
C18 C -0.3712(5) 0.3915(6) 0.1152(4) 0.0502(13) Uani 1 1 d . . . . .
C19 C -0.4755(5) 0.4058(5) 0.0680(4) 0.0441(12) Uani 1 1 d . . . . .
C20 C -0.5953(5) 0.3380(6) 0.0735(5) 0.0555(14) Uani 1 1 d . . . . .
H20 H -0.6107 0.2834 0.1070 0.067 Uiso 1 1 calc R U . . .
C21 C -0.4503(5) 0.4936(5) 0.0216(3) 0.0395(11) Uani 1 1 d . . . . .
C22 C -0.3275(4) 0.5652(5) 0.0161(4) 0.0406(11) Uani 1 1 d . . . . .
C23 C -0.3059(5) 0.6500(6) -0.0295(4) 0.0521(14) Uani 1 1 d . . . . .
H23 H -0.2243 0.6999 -0.0310 0.062 Uiso 1 1 calc R U . . .
C24 C -0.2211(5) 0.5517(6) 0.0616(4) 0.0451(12) 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 N1 2.044(4) . ?
Zn1 N3 2.075(5) . ?
Zn1 I2 2.5351(13) . ?
Zn1 I1 2.5773(9) . ?
N1 C5 1.336(7) . ?
N1 C1 1.338(8) . ?
N2 C12 1.383(7) . ?
N2 C6 1.392(7) . ?
N2 C3 1.455(7) . ?
N3 C17 1.318(7) . ?
N3 C13 1.352(7) . ?
N4 C18 1.393(7) . ?
N4 C24 1.394(7) . ?
N4 C15 1.454(6) . ?
O1 C6 1.209(7) . ?
O2 C12 1.232(6) . ?
O3 C18 1.200(7) . ?
O4 C24 1.237(6) . ?
C1 C2 1.392(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.358(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(8) . ?
C4 C5 1.353(8) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.487(7) . ?
C7 C9 1.395(7) . ?
C7 C8 1.406(7) . ?
C8 C11 1.351(8) 2_776 ?
C8 H8 0.9300 . ?
C9 C9 1.405(10) 2_776 ?
C9 C10 1.416(7) . ?
C10 C11 1.387(7) . ?
C10 C12 1.462(7) . ?
C11 C8 1.351(8) 2_776 ?
C11 H11 0.9300 . ?
C13 C14 1.355(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.356(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.341(8) . ?
C16 C17 1.374(8) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.482(7) . ?
C19 C20 1.365(8) . ?
C19 C21 1.409(7) . ?
C20 C23 1.386(8) 2_465 ?
C20 H20 0.9300 . ?
C21 C21 1.395(10) 2_465 ?
C21 C22 1.405(7) . ?
C22 C23 1.373(8) . ?
C22 C24 1.485(7) . ?
C23 C20 1.386(8) 2_465 ?
C23 H23 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Zn1 N3 106.40(19) . . ?
N1 Zn1 I2 107.59(13) . . ?
N3 Zn1 I2 109.76(14) . . ?
N1 Zn1 I1 104.44(13) . . ?
N3 Zn1 I1 105.86(13) . . ?
I2 Zn1 I1 121.79(4) . . ?
C5 N1 C1 115.7(5) . . ?
C5 N1 Zn1 120.3(4) . . ?
C1 N1 Zn1 123.9(4) . . ?
C12 N2 C6 125.6(4) . . ?
C12 N2 C3 117.7(4) . . ?
C6 N2 C3 116.7(4) . . ?
C17 N3 C13 117.2(5) . . ?
C17 N3 Zn1 121.3(4) . . ?
C13 N3 Zn1 121.1(4) . . ?
C18 N4 C24 125.9(4) . . ?
C18 N4 C15 116.8(4) . . ?
C24 N4 C15 117.1(4) . . ?
N1 C1 C2 123.8(6) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C3 C2 C1 117.3(6) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 120.0(5) . . ?
C2 C3 N2 119.4(5) . . ?
C4 C3 N2 120.5(5) . . ?
C5 C4 C3 118.6(5) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 124.2(6) . . ?
N1 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
O1 C6 N2 120.5(5) . . ?
O1 C6 C7 123.6(5) . . ?
N2 C6 C7 115.9(4) . . ?
C9 C7 C8 119.8(5) . . ?
C9 C7 C6 120.3(4) . . ?
C8 C7 C6 119.9(5) . . ?
C11 C8 C7 120.2(5) 2_776 . ?
C11 C8 H8 119.9 2_776 . ?
C7 C8 H8 119.9 . . ?
C7 C9 C9 119.9(6) . 2_776 ?
C7 C9 C10 121.2(5) . . ?
C9 C9 C10 118.9(6) 2_776 . ?
C11 C10 C9 119.6(5) . . ?
C11 C10 C12 121.1(5) . . ?
C9 C10 C12 119.3(5) . . ?
C8 C11 C10 121.6(5) 2_776 . ?
C8 C11 H11 119.2 2_776 . ?
C10 C11 H11 119.2 . . ?
O2 C12 N2 119.1(5) . . ?
O2 C12 C10 123.0(5) . . ?
N2 C12 C10 117.8(4) . . ?
N3 C13 C14 122.1(5) . . ?
N3 C13 H13 118.9 . . ?
C14 C13 H13 118.9 . . ?
C13 C14 C15 119.6(5) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 118.7(5) . . ?
C16 C15 N4 120.5(5) . . ?
C14 C15 N4 120.7(5) . . ?
C15 C16 C17 119.6(5) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
N3 C17 C16 122.4(5) . . ?
N3 C17 H17 118.8 . . ?
C16 C17 H17 118.8 . . ?
O3 C18 N4 120.1(5) . . ?
O3 C18 C19 123.5(5) . . ?
N4 C18 C19 116.4(5) . . ?
C20 C19 C21 120.3(5) . . ?
C20 C19 C18 119.7(5) . . ?
C21 C19 C18 120.0(5) . . ?
C19 C20 C23 120.5(5) . 2_465 ?
C19 C20 H20 119.8 . . ?
C23 C20 H20 119.8 2_465 . ?
C21 C21 C22 119.8(6) 2_465 . ?
C21 C21 C19 119.1(6) 2_465 . ?
C22 C21 C19 121.1(5) . . ?
C23 C22 C21 119.7(5) . . ?
C23 C22 C24 120.1(5) . . ?
C21 C22 C24 120.2(5) . . ?
C22 C23 C20 120.6(5) . 2_465 ?
C22 C23 H23 119.7 . . ?
C20 C23 H23 119.7 2_465 . ?
O4 C24 N4 121.4(5) . . ?
O4 C24 C22 122.4(5) . . ?
N4 C24 C22 116.2(4) . . ?

_refine_diff_density_max         0.927
_refine_diff_density_min         -0.869
_refine_diff_density_rms         0.126

_shelxl_version_number           2014/6

