# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_compound1
_database_code_depnum_ccdc_archive 'CCDC 1440845'
_audit_update_record             
;
2015-12-07 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 N4 O4 S Zn, H2 O'
_chemical_formula_sum            'C18 H14 N4 O5 S Zn'
_chemical_formula_weight         463.78

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'
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'
S S 0.1246 0.1234 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   23.245(3)
_cell_length_b                   9.9259(12)
_cell_length_c                   17.277(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.810(2)
_cell_angle_gamma                90
_cell_volume                     3815.9(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6902
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      25.15

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_F_000             1888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.23
_exptl_absorpt_coefficient_mu    1.436
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.525
_exptl_absorpt_correction_T_max  0.719
_exptl_absorpt_process_details   MULTI-SCAN
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10641
_diffrn_reflns_av_unetI/netI     0.0145
_diffrn_reflns_av_R_equivalents  0.0138
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.133
_diffrn_reflns_theta_max         25.147
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3415
_reflns_number_gt                3158
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0180P)²+8.0052P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3352
_refine_ls_number_parameters     270
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0238
_refine_ls_R_factor_gt           0.0218
_refine_ls_wR_factor_ref         0.0515
_refine_ls_wR_factor_gt          0.0506
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_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 0.38224(2) 0.30502(2) 0.04608(2) 0.01798(7) Uani 1 1 d . . . . .
S1 S 0.41690(2) -0.03231(5) 0.29040(3) 0.02469(11) Uani 1 1 d . . . . .
O4 O 0.34925(6) -0.18840(14) 0.45279(7) 0.0266(3) Uani 1 1 d . . . . .
O1 O 0.34680(6) 0.24902(14) 0.13420(7) 0.0260(3) Uani 1 1 d . . . . .
O2 O 0.41985(6) 0.10560(14) 0.13524(8) 0.0304(3) Uani 1 1 d . . . . .
O3 O 0.44047(7) -0.20634(16) 0.43792(9) 0.0400(4) Uani 1 1 d . . . . .
N12 N 0.18786(7) 0.80973(17) -0.17338(10) 0.0293(4) Uani 1 1 d . . . . .
N11 N 0.32463(6) 0.46779(15) 0.00619(8) 0.0201(3) Uani 1 1 d . . . . .
N13 N 0.13101(7) 0.86041(18) -0.21652(10) 0.0328(4) Uani 1 1 d . . . . .
N14 N 0.46399(6) 0.38703(15) 0.09603(8) 0.0207(3) Uani 1 1 d . . . . .
C2 C 0.02316(9) 0.9323(2) -0.33132(12) 0.0292(4) Uani 1 1 d . . . . .
H2 H 0.0254 0.8433 -0.3140 0.035 Uiso 1 1 calc R U . . .
C6 C 0.22223(8) 0.53761(19) -0.02711(10) 0.0220(4) Uani 1 1 d . . . . .
H6 H 0.1842 0.5261 -0.0206 0.026 Uiso 1 1 calc R U . . .
C14 C 0.36488(8) 0.07397(19) 0.22960(10) 0.0218(4) Uani 1 1 d . . . . .
C7 C 0.26862(8) 0.45423(18) 0.01243(10) 0.0210(4) Uani 1 1 d . . . . .
H7 H 0.2609 0.3857 0.0448 0.025 Uiso 1 1 calc R U . . .
C17 C 0.36899(8) -0.06866(19) 0.34670(10) 0.0228(4) Uani 1 1 d . . . . .
C8 C 0.18154(8) 0.71910(19) -0.12428(11) 0.0242(4) Uani 1 1 d . . . . .
H8 H 0.1436 0.7033 -0.1184 0.029 Uiso 1 1 calc R U . . .
C4 C 0.29097(8) 0.6563(2) -0.08124(11) 0.0262(4) Uani 1 1 d . . . . .
H4 H 0.3000 0.7253 -0.1123 0.031 Uiso 1 1 calc R U . . .
C1 C 0.13213(9) 0.9608(2) -0.26023(11) 0.0296(4) Uani 1 1 d . . . . .
H1 H 0.1683 1.0006 -0.2604 0.035 Uiso 1 1 calc R U . . .
C13 C 0.37885(8) 0.14612(19) 0.16216(10) 0.0226(4) Uani 1 1 d . . . . .
C15 C 0.31336(8) 0.0806(2) 0.25247(10) 0.0245(4) Uani 1 1 d . . . . .
H15 H 0.2806 0.1342 0.2268 0.029 Uiso 1 1 calc R U . . .
C3 C 0.33502(8) 0.5697(2) -0.03903(11) 0.0262(4) Uani 1 1 d . . . . .
H3 H 0.3740 0.5824 -0.0419 0.031 Uiso 1 1 calc R U . . .
C18 C 0.38865(9) -0.16153(19) 0.41697(10) 0.0239(4) Uani 1 1 d . . . . .
C5 C 0.23252(8) 0.63919(19) -0.07680(10) 0.0210(4) Uani 1 1 d . . . . .
C9 C 0.07429(8) 1.0137(2) -0.31140(11) 0.0249(4) Uani 1 1 d . . . . .
C12 C 0.51335(8) 0.3097(2) 0.11324(11) 0.0255(4) Uani 1 1 d . . . . .
H12 H 0.5101 0.2218 0.0938 0.031 Uiso 1 1 calc R U . . .
C11 C 0.46967(8) 0.5144(2) 0.12319(11) 0.0267(4) Uani 1 1 d . . . . .
H11 H 0.4357 0.5691 0.1106 0.032 Uiso 1 1 calc R U . . .
C10 C 0.06884(8) 1.1444(2) -0.34126(11) 0.0256(4) Uani 1 1 d . . . . .
H10 H 0.1023 1.2005 -0.3307 0.031 Uiso 1 1 calc R U . . .
C16 C 0.31544(8) -0.0025(2) 0.31906(10) 0.0248(4) Uani 1 1 d . . . . .
H16 H 0.2839 -0.0115 0.3417 0.030 Uiso 1 1 calc R U . . .
O5 O 0.06188(10) 0.3553(3) 0.44277(17) 0.0694(7) Uani 1 1 d . . . . .
H5A H 0.0345(16) 0.324(4) 0.449(2) 0.084(13) Uiso 1 1 d . . . . .
H5B H 0.0607(18) 0.418(4) 0.415(2) 0.108(16) 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 O4 1.9523(12) 6 ?
Zn1 O1 2.0077(12) . ?
Zn1 N14 2.0174(15) . ?
Zn1 N11 2.0845(15) . ?
Zn1 C13 2.5705(18) . ?
S1 C17 1.7155(18) . ?
S1 C14 1.7158(18) . ?
O4 C18 1.273(2) . ?
O4 Zn1 1.9522(12) 6_556 ?
O1 C13 1.274(2) . ?
O2 C13 1.242(2) . ?
O3 C18 1.236(2) . ?
N12 C8 1.274(2) . ?
N12 N13 1.409(2) . ?
N11 C7 1.344(2) . ?
N11 C3 1.342(2) . ?
N13 C1 1.255(3) . ?
N14 C12 1.340(2) . ?
N14 C11 1.342(2) . ?
C2 C11 1.371(3) 8_465 ?
C2 C9 1.395(3) . ?
C2 H2 0.9300 . ?
C6 C7 1.374(2) . ?
C6 C5 1.389(3) . ?
C6 H6 0.9300 . ?
C14 C15 1.367(3) . ?
C14 C13 1.481(2) . ?
C7 H7 0.9300 . ?
C17 C16 1.366(3) . ?
C17 C18 1.487(2) . ?
C8 C5 1.464(3) . ?
C8 H8 0.9300 . ?
C4 C3 1.374(3) . ?
C4 C5 1.393(3) . ?
C4 H4 0.9300 . ?
C1 C9 1.476(3) . ?
C1 H1 0.9300 . ?
C15 C16 1.405(3) . ?
C15 H15 0.9300 . ?
C3 H3 0.9300 . ?
C9 C10 1.388(3) . ?
C12 C10 1.379(3) 8_566 ?
C12 H12 0.9300 . ?
C11 C2 1.371(3) 8_566 ?
C11 H11 0.9300 . ?
C10 C12 1.379(3) 8_465 ?
C10 H10 0.9300 . ?
C16 H16 0.9300 . ?
O5 H5A 0.75(4) . ?
O5 H5B 0.79(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
O4 Zn1 O1 108.21(6) 6 . ?
O4 Zn1 N14 133.55(6) 6 . ?
O1 Zn1 N14 109.25(6) . . ?
O4 Zn1 N11 97.19(6) 6 . ?
O1 Zn1 N11 95.74(5) . . ?
N14 Zn1 N11 105.33(6) . . ?
O4 Zn1 C13 100.78(6) 6 . ?
O1 Zn1 C13 29.14(6) . . ?
N14 Zn1 C13 98.71(6) . . ?
N11 Zn1 C13 124.88(6) . . ?
C17 S1 C14 91.05(9) . . ?
C18 O4 Zn1 111.07(12) . 6_556 ?
C13 O1 Zn1 100.73(11) . . ?
C8 N12 N13 109.47(16) . . ?
C7 N11 C3 117.64(15) . . ?
C7 N11 Zn1 116.14(12) . . ?
C3 N11 Zn1 124.76(12) . . ?
C1 N13 N12 114.97(17) . . ?
C12 N14 C11 118.08(16) . . ?
C12 N14 Zn1 120.26(12) . . ?
C11 N14 Zn1 121.00(12) . . ?
C11 C2 C9 118.99(18) 8_465 . ?
C11 C2 H2 120.5 8_465 . ?
C9 C2 H2 120.5 . . ?
C7 C6 C5 119.60(16) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C15 C14 C13 127.87(17) . . ?
C15 C14 S1 111.95(13) . . ?
C13 C14 S1 120.18(14) . . ?
N11 C7 C6 122.60(16) . . ?
N11 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C16 C17 C18 128.11(16) . . ?
C16 C17 S1 112.10(13) . . ?
C18 C17 S1 119.78(14) . . ?
N12 C8 C5 121.68(17) . . ?
N12 C8 H8 119.2 . . ?
C5 C8 H8 119.2 . . ?
C3 C4 C5 118.91(17) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N13 C1 C9 117.97(18) . . ?
N13 C1 H1 121.0 . . ?
C9 C1 H1 121.0 . . ?
O2 C13 O1 123.06(16) . . ?
O2 C13 C14 120.29(17) . . ?
O1 C13 C14 116.65(16) . . ?
O2 C13 Zn1 72.94(10) . . ?
O1 C13 Zn1 50.12(8) . . ?
C14 C13 Zn1 166.75(14) . . ?
C14 C15 C16 112.51(17) . . ?
C14 C15 H15 123.7 . . ?
C16 C15 H15 123.7 . . ?
N11 C3 C4 123.28(17) . . ?
N11 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
O3 C18 O4 124.02(17) . . ?
O3 C18 C17 120.36(17) . . ?
O4 C18 C17 115.61(16) . . ?
C6 C5 C4 117.87(17) . . ?
C6 C5 C8 118.91(16) . . ?
C4 C5 C8 123.17(17) . . ?
C10 C9 C2 118.02(17) . . ?
C10 C9 C1 121.64(18) . . ?
C2 C9 C1 120.34(18) . . ?
N14 C12 C10 122.48(18) . 8_566 ?
N14 C12 H12 118.8 . . ?
C10 C12 H12 118.8 8_566 . ?
N14 C11 C2 123.05(18) . 8_566 ?
N14 C11 H11 118.5 . . ?
C2 C11 H11 118.5 8_566 . ?
C12 C10 C9 119.34(18) 8_465 . ?
C12 C10 H10 120.3 8_465 . ?
C9 C10 H10 120.3 . . ?
C17 C16 C15 112.37(16) . . ?
C17 C16 H16 123.8 . . ?
C15 C16 H16 123.8 . . ?
H5A O5 H5B 123(4) . . ?

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
C8 N12 N13 C1 172.39(18) . . . . ?
C17 S1 C14 C15 0.24(15) . . . . ?
C17 S1 C14 C13 179.81(15) . . . . ?
C3 N11 C7 C6 1.8(3) . . . . ?
Zn1 N11 C7 C6 -165.02(13) . . . . ?
C5 C6 C7 N11 1.1(3) . . . . ?
C14 S1 C17 C16 0.51(15) . . . . ?
C14 S1 C17 C18 -178.71(15) . . . . ?
N13 N12 C8 C5 174.03(16) . . . . ?
N12 N13 C1 C9 175.96(17) . . . . ?
Zn1 O1 C13 O2 0.5(2) . . . . ?
Zn1 O1 C13 C14 -179.13(13) . . . . ?
C15 C14 C13 O2 -161.26(19) . . . . ?
S1 C14 C13 O2 19.3(2) . . . . ?
C15 C14 C13 O1 18.4(3) . . . . ?
S1 C14 C13 O1 -161.05(13) . . . . ?
C15 C14 C13 Zn1 15.5(7) . . . . ?
S1 C14 C13 Zn1 -164.0(5) . . . . ?
C13 C14 C15 C16 179.56(18) . . . . ?
S1 C14 C15 C16 -0.9(2) . . . . ?
C7 N11 C3 C4 -2.7(3) . . . . ?
Zn1 N11 C3 C4 162.95(15) . . . . ?
C5 C4 C3 N11 0.6(3) . . . . ?
Zn1 O4 C18 O3 1.5(2) 6_556 . . . ?
Zn1 O4 C18 C17 -177.68(12) 6_556 . . . ?
C16 C17 C18 O3 -174.8(2) . . . . ?
S1 C17 C18 O3 4.3(3) . . . . ?
C16 C17 C18 O4 4.4(3) . . . . ?
S1 C17 C18 O4 -176.51(14) . . . . ?
C7 C6 C5 C4 -3.1(3) . . . . ?
C7 C6 C5 C8 174.42(16) . . . . ?
C3 C4 C5 C6 2.3(3) . . . . ?
C3 C4 C5 C8 -175.08(18) . . . . ?
N12 C8 C5 C6 -177.04(18) . . . . ?
N12 C8 C5 C4 0.4(3) . . . . ?
C11 C2 C9 C10 -2.2(3) 8_465 . . . ?
C11 C2 C9 C1 177.95(18) 8_465 . . . ?
N13 C1 C9 C10 159.41(19) . . . . ?
N13 C1 C9 C2 -20.7(3) . . . . ?
C11 N14 C12 C10 1.3(3) . . . 8_566 ?
Zn1 N14 C12 C10 -169.43(14) . . . 8_566 ?
C12 N14 C11 C2 -1.2(3) . . . 8_566 ?
Zn1 N14 C11 C2 169.43(15) . . . 8_566 ?
C2 C9 C10 C12 2.1(3) . . . 8_465 ?
C1 C9 C10 C12 -178.01(17) . . . 8_465 ?
C18 C17 C16 C15 178.03(18) . . . . ?
S1 C17 C16 C15 -1.1(2) . . . . ?
C14 C15 C16 C17 1.3(2) . . . . ?

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.046

_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_COMPOUND_3
_database_code_depnum_ccdc_archive 'CCDC 1440846'
_audit_update_record             
;
2016-02-08 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;
_audit_creation_date             2016-02-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H16 N4 O4 Zn'
_chemical_formula_sum            'C24 H16 N4 O4 Zn'
_chemical_formula_weight         489.80
_chemical_melting_point          ?
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'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7117(12)
_cell_length_b                   11.0488(16)
_cell_length_c                   13.2930(19)
_cell_angle_alpha                69.790(4)
_cell_angle_beta                 77.976(4)
_cell_angle_gamma                71.660(4)
_cell_volume                     1132.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6264
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.04
_cell_measurement_theta_min      2.72
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.122
_exptl_absorpt_correction_T_max  0.773
_exptl_absorpt_correction_T_min  0.622
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_process_details   MULTI-SCAN
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0092
_diffrn_reflns_av_unetI/netI     0.0046
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5403
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.448
_diffrn_reflns_theta_min         1.643
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5179
_reflns_number_total             5179
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.728
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         5179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0594
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0338P)²+5.3543P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1421
_refine_ls_wR_factor_ref         0.1421
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18),
 C24(H24), C25(H25), C27(H27), C28(H28), C32(H32), C33(H33), C37(H37), C38(H38)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.73023(5) 0.47048(4) 0.22681(4) 0.03077(13) Uani 1 1 d . . . . .
O1 O 0.7900(8) 0.6443(5) 0.0003(4) 0.1038(19) Uani 1 1 d . . . . .
O2 O 0.8155(4) 0.6241(3) 0.1632(3) 0.0561(9) Uani 1 1 d . . . . .
O5 O 0.5609(4) 0.4389(4) 0.3518(3) 0.0577(9) Uani 1 1 d . . . . .
O6 O 0.4246(5) 0.6254(5) 0.2520(3) 0.0867(15) Uani 1 1 d . . . . .
N1 N 0.6856(4) 0.3595(3) 0.1449(3) 0.0326(6) Uani 1 1 d . . . . .
N3 N 0.9205(4) 0.3365(3) 0.3148(3) 0.0360(7) Uani 1 1 d . . . . .
N4 N 0.5163(5) 0.0285(4) 0.0352(3) 0.0453(8) Uani 1 1 d . . . . .
N5 N 1.4504(5) 0.0488(5) 0.4611(4) 0.0648(12) Uani 1 1 d . . . . .
C1 C 0.8915(5) 0.8032(4) 0.0264(4) 0.0388(9) Uani 1 1 d . . . . .
C2 C 0.9097(6) 0.8688(5) -0.0865(4) 0.0504(11) Uani 1 1 d . . . . .
H2 H 0.8851 0.8350 -0.1344 0.060 Uiso 1 1 calc R . . . .
C3 C 0.9640(6) 0.9825(5) -0.1244(4) 0.0489(11) Uani 1 1 d . . . . .
H3 H 0.9724 1.0266 -0.1981 0.059 Uiso 1 1 calc R . . . .
C4 C 1.0059(5) 1.0322(4) -0.0554(3) 0.0351(8) Uani 1 1 d . . . . .
C6 C 0.9300(5) 0.8518(4) 0.0936(4) 0.0406(9) Uani 1 1 d . . . . .
H6 H 0.9154 0.8099 0.1674 0.049 Uiso 1 1 calc R . . . .
C11 C 0.8291(5) 0.6810(4) 0.0645(4) 0.0417(9) Uani 1 1 d . . . . .
C13 C 0.6359(6) 0.2484(4) 0.2015(4) 0.0445(10) Uani 1 1 d . . . . .
H13 H 0.6283 0.2230 0.2764 0.053 Uiso 1 1 calc R . . . .
C14 C 0.5964(5) 0.1719(4) 0.1555(4) 0.0438(10) Uani 1 1 d . . . . .
H14 H 0.5632 0.0961 0.1985 0.053 Uiso 1 1 calc R . . . .
C15 C 0.6057(4) 0.2069(4) 0.0448(3) 0.0358(8) Uani 1 1 d . . . . .
C16 C 0.6620(6) 0.3179(4) -0.0143(4) 0.0472(10) Uani 1 1 d . . . . .
H16 H 0.6746 0.3434 -0.0893 0.057 Uiso 1 1 calc R . . . .
C17 C 0.6991(6) 0.3899(4) 0.0385(4) 0.0437(10) Uani 1 1 d . . . . .
H17 H 0.7359 0.4646 -0.0028 0.052 Uiso 1 1 calc R . . . .
C18 C 0.5632(5) 0.1312(4) -0.0122(4) 0.0438(10) Uani 1 1 d . . . . .
H18 H 0.5717 0.1615 -0.0872 0.053 Uiso 1 1 calc R . . . .
C24 C 0.8860(6) 0.2617(5) 0.4168(4) 0.0501(11) Uani 1 1 d . . . . .
H24 H 0.7780 0.2697 0.4465 0.060 Uiso 1 1 calc R . . . .
C25 C 1.0108(6) 0.1718(5) 0.4788(4) 0.0530(11) Uani 1 1 d . . . . .
H25 H 0.9853 0.1190 0.5482 0.064 Uiso 1 1 calc R . . . .
C26 C 1.1749(6) 0.1619(5) 0.4353(4) 0.0502(11) Uani 1 1 d . . . . .
C27 C 1.2043(6) 0.2413(6) 0.3307(5) 0.0611(14) Uani 1 1 d . . . . .
H27 H 1.3106 0.2368 0.2984 0.073 Uiso 1 1 calc R . . . .
C28 C 1.0742(5) 0.3281(5) 0.2739(4) 0.0490(11) Uani 1 1 d . . . . .
H28 H 1.0965 0.3822 0.2044 0.059 Uiso 1 1 calc R . . . .
C29 C 0.4320(5) 0.5267(5) 0.3298(4) 0.0433(9) Uani 1 1 d . . . . .
C31 C 0.2828(5) 0.5059(4) 0.4058(4) 0.0400(9) Uani 1 1 d . . . . .
C32 C 0.1299(5) 0.5739(5) 0.3773(4) 0.0521(11) Uani 1 1 d . . . . .
H32 H 0.1173 0.6385 0.3104 0.062 Uiso 1 1 calc R . . . .
C33 C 0.2995(6) 0.4107(6) 0.5093(4) 0.0562(12) Uani 1 1 d . . . . .
H33 H 0.4034 0.3631 0.5285 0.067 Uiso 1 1 calc R . . . .
C37 C 1.3020(7) 0.0693(6) 0.4986(6) 0.0704(16) Uani 1 1 d . . . . .
H37 H 1.2741 0.0228 0.5698 0.085 Uiso 1 1 calc R . . . .
C38 C 0.1680(6) 0.3864(6) 0.5819(4) 0.0579(13) Uani 1 1 d . . . . .
H38 H 0.1813 0.3269 0.6508 0.069 Uiso 1 1 calc R . . . .
C39 C -0.0142(5) 0.5467(4) 0.4504(4) 0.0430(9) 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 O2 1.921(3) . ?
Zn1 O5 1.991(3) . ?
Zn1 N1 2.058(3) . ?
Zn1 N3 2.091(3) . ?
O1 C11 1.206(6) . ?
O2 C11 1.242(5) . ?
O5 C29 1.242(5) . ?
O6 C29 1.211(6) . ?
N1 C13 1.349(5) . ?
N1 C17 1.325(5) . ?
N3 C24 1.351(6) . ?
N3 C28 1.324(5) . ?
N4 N4 1.410(6) 2_655 ?
N4 C18 1.241(6) . ?
N5 N5 1.412(8) 2_856 ?
N5 C37 1.263(7) . ?
C1 C2 1.423(6) . ?
C1 C6 1.329(6) . ?
C1 C11 1.500(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(6) . ?
C4 C4 1.394(8) 2_775 ?
C4 C6 1.447(5) 2_775 ?
C6 C4 1.448(5) 2_775 ?
C6 H6 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.354(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(6) . ?
C15 C16 1.384(6) . ?
C15 C18 1.470(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.368(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.406(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.411(7) . ?
C26 C27 1.386(7) . ?
C26 C37 1.435(7) . ?
C27 H27 0.9300 . ?
C27 C28 1.395(7) . ?
C28 H28 0.9300 . ?
C29 C31 1.497(6) . ?
C31 C32 1.366(6) . ?
C31 C33 1.418(7) . ?
C32 H32 0.9300 . ?
C32 C39 1.462(6) . ?
C33 H33 0.9300 . ?
C33 C38 1.367(7) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C38 C39 1.387(6) 2_566 ?
C39 C38 1.387(6) 2_566 ?
C39 C39 1.378(9) 2_566 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Zn1 O5 128.29(16) . . ?
O2 Zn1 N1 125.99(14) . . ?
O2 Zn1 N3 100.39(14) . . ?
O5 Zn1 N1 98.00(13) . . ?
O5 Zn1 N3 93.53(14) . . ?
N1 Zn1 N3 103.04(13) . . ?
C11 O2 Zn1 123.0(3) . . ?
C29 O5 Zn1 108.8(3) . . ?
C13 N1 Zn1 119.1(3) . . ?
C17 N1 Zn1 124.8(3) . . ?
C17 N1 C13 116.1(3) . . ?
C24 N3 Zn1 119.4(3) . . ?
C28 N3 Zn1 121.1(3) . . ?
C28 N3 C24 119.4(4) . . ?
C18 N4 N4 113.4(5) . 2_655 ?
C37 N5 N5 111.0(6) . 2_856 ?
C2 C1 C11 118.0(4) . . ?
C6 C1 C2 119.2(4) . . ?
C6 C1 C11 122.7(4) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C4 120.4(4) . 2_775 ?
C3 C4 C6 122.3(4) . 2_775 ?
C4 C4 C6 117.3(5) 2_775 2_775 ?
C1 C6 C4 122.1(4) . 2_775 ?
C1 C6 H6 119.0 . . ?
C4 C6 H6 119.0 2_775 . ?
O1 C11 O2 122.8(4) . . ?
O1 C11 C1 119.9(4) . . ?
O2 C11 C1 117.2(4) . . ?
N1 C13 H13 118.1 . . ?
N1 C13 C14 123.8(4) . . ?
C14 C13 H13 118.1 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.7(4) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 117.1(4) . . ?
C14 C15 C18 123.6(4) . . ?
C16 C15 C18 119.3(4) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.5(4) . . ?
C17 C16 H16 120.3 . . ?
N1 C17 C16 123.8(4) . . ?
N1 C17 H17 118.1 . . ?
C16 C17 H17 118.1 . . ?
N4 C18 C15 122.9(4) . . ?
N4 C18 H18 118.5 . . ?
C15 C18 H18 118.5 . . ?
N3 C24 H24 119.5 . . ?
N3 C24 C25 121.0(4) . . ?
C25 C24 H24 119.5 . . ?
C24 C25 H25 120.1 . . ?
C24 C25 C26 119.7(4) . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C37 119.6(5) . . ?
C27 C26 C25 117.2(4) . . ?
C27 C26 C37 123.2(5) . . ?
C26 C27 H27 120.0 . . ?
C26 C27 C28 119.9(4) . . ?
C28 C27 H27 120.0 . . ?
N3 C28 C27 122.7(4) . . ?
N3 C28 H28 118.7 . . ?
C27 C28 H28 118.7 . . ?
O5 C29 C31 116.5(4) . . ?
O6 C29 O5 122.9(4) . . ?
O6 C29 C31 120.6(4) . . ?
C32 C31 C29 121.9(4) . . ?
C32 C31 C33 118.6(4) . . ?
C33 C31 C29 119.5(4) . . ?
C31 C32 H32 119.5 . . ?
C31 C32 C39 121.0(5) . . ?
C39 C32 H32 119.5 . . ?
C31 C33 H33 118.9 . . ?
C38 C33 C31 122.2(5) . . ?
C38 C33 H33 118.9 . . ?
N5 C37 C26 122.4(6) . . ?
N5 C37 H37 118.8 . . ?
C26 C37 H37 118.8 . . ?
C33 C38 H38 121.0 . . ?
C33 C38 C39 117.9(5) . 2_566 ?
C39 C38 H38 121.0 2_566 . ?
C38 C39 C32 119.9(4) 2_566 . ?
C39 C39 C32 116.1(5) 2_566 . ?
C39 C39 C38 124.0(6) 2_566 2_566 ?

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
Zn1 O2 C11 O1 -0.1(7) . . . . ?
Zn1 O2 C11 C1 177.6(3) . . . . ?
Zn1 O5 C29 O6 -11.3(6) . . . . ?
Zn1 O5 C29 C31 169.5(3) . . . . ?
Zn1 N1 C13 C14 177.0(4) . . . . ?
Zn1 N1 C17 C16 -177.0(4) . . . . ?
Zn1 N3 C24 C25 -179.2(4) . . . . ?
Zn1 N3 C28 C27 179.1(4) . . . . ?
O5 C29 C31 C32 -162.7(4) . . . . ?
O5 C29 C31 C33 15.6(6) . . . . ?
O6 C29 C31 C32 18.1(7) . . . . ?
O6 C29 C31 C33 -163.6(5) . . . . ?
N1 C13 C14 C15 -0.2(7) . . . . ?
N3 C24 C25 C26 1.8(8) . . . . ?
N4 N4 C18 C15 -179.5(4) 2_655 . . . ?
N5 N5 C37 C26 -178.6(6) 2_856 . . . ?
C1 C2 C3 C4 2.0(8) . . . . ?
C2 C1 C6 C4 -1.6(7) . . . 2_775 ?
C2 C1 C11 O1 -2.9(7) . . . . ?
C2 C1 C11 O2 179.3(4) . . . . ?
C2 C3 C4 C4 -0.1(8) . . . 2_775 ?
C2 C3 C4 C6 177.3(4) . . . 2_775 ?
C6 C1 C2 C3 -1.2(7) . . . . ?
C6 C1 C11 O1 177.2(5) . . . . ?
C6 C1 C11 O2 -0.6(6) . . . . ?
C11 C1 C2 C3 178.9(4) . . . . ?
C11 C1 C6 C4 178.4(4) . . . 2_775 ?
C13 N1 C17 C16 1.7(7) . . . . ?
C13 C14 C15 C16 2.4(6) . . . . ?
C13 C14 C15 C18 -179.1(4) . . . . ?
C14 C15 C16 C17 -2.6(7) . . . . ?
C14 C15 C18 N4 -0.6(7) . . . . ?
C15 C16 C17 N1 0.5(7) . . . . ?
C16 C15 C18 N4 177.9(4) . . . . ?
C17 N1 C13 C14 -1.9(6) . . . . ?
C18 C15 C16 C17 178.9(4) . . . . ?
C24 N3 C28 C27 2.0(7) . . . . ?
C24 C25 C26 C27 -1.3(8) . . . . ?
C24 C25 C26 C37 -179.6(5) . . . . ?
C25 C26 C27 C28 1.2(8) . . . . ?
C25 C26 C37 N5 174.5(6) . . . . ?
C26 C27 C28 N3 -1.6(8) . . . . ?
C27 C26 C37 N5 -3.7(9) . . . . ?
C28 N3 C24 C25 -2.1(7) . . . . ?
C29 C31 C32 C39 176.5(4) . . . . ?
C29 C31 C33 C38 -179.4(5) . . . . ?
C31 C32 C39 C38 -177.7(5) . . . 2_566 ?
C31 C32 C39 C39 2.3(8) . . . 2_566 ?
C31 C33 C38 C39 3.4(8) . . . 2_566 ?
C32 C31 C33 C38 -1.1(7) . . . . ?
C33 C31 C32 C39 -1.8(7) . . . . ?
C37 C26 C27 C28 179.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_Compound_2
_database_code_depnum_ccdc_archive 'CCDC 1440847'
_audit_update_record             
;
2016-03-21 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H10 N5 O4 Zn, C2 O'
_chemical_formula_sum            'C22 H10 N5 O5 Zn'
_chemical_formula_weight         489.74

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'

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

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

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

_cell_length_a                   24.568(5)
_cell_length_b                   10.146(2)
_cell_length_c                   17.994(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.863(6)
_cell_angle_gamma                90
_cell_volume                     4162.4(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9903
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      25.08

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_F_000             1976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    1.226
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.612
_exptl_absorpt_correction_T_max  0.736
_exptl_absorpt_process_details   MULTI-SCAN
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            64313
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.197
_diffrn_reflns_theta_max         25.506
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3880
_reflns_number_gt                3134
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.1017P)²+30.1255P] 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         3880
_refine_ls_number_parameters     271
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_ref         0.1869
_refine_ls_wR_factor_gt          0.1743
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.002
_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 0.38193(2) 0.29570(5) 1.04321(3) 0.0299(2) Uiso 1 1 d . . . . .
O1 O 0.40907(17) 0.2245(4) 0.9583(2) 0.0499(10) Uani 1 1 d . . . . .
O2 O 0.32187(17) 0.1448(4) 0.9406(2) 0.0477(9) Uani 1 1 d . . . . .
O3 O 0.41680(19) 0.1183(4) 1.1300(2) 0.0518(10) Uani 1 1 d . . . . .
O4 O 0.34610(16) 0.2506(4) 1.1269(2) 0.0444(8) Uiso 1 1 d . . . . .
N1 N 0.32430(16) 0.4480(4) 0.9897(2) 0.0328(8) Uani 1 1 d . . . . .
N2 N 0.45866(19) 0.3981(4) 1.1064(3) 0.0412(10) Uiso 1 1 d . . . . .
N3 N 0.2778(3) -0.1767(6) 0.7105(4) 0.0703(16) Uani 1 1 d . . . . .
H3A H 0.2782 -0.2287 0.6715 0.084 Uiso 1 1 calc R U . . .
H3B H 0.2478 -0.1784 0.7260 0.084 Uiso 1 1 calc R U . . .
N4 N 0.1946(2) 0.8085(5) 0.8182(3) 0.0572(13) Uiso 1 1 d . . . . .
N5A N 0.1549(4) 0.9063(8) 0.7848(5) 0.0336(17) Uiso 0.5 1 d . . P A 1
C2AA C 0.2751(2) 0.4588(5) 1.0045(3) 0.0386(11) Uani 1 1 d . . . . .
H2AA H 0.2694 0.4009 1.0425 0.046 Uiso 1 1 calc R U . . .
C2 C 0.2322(2) 0.5508(5) 0.9669(3) 0.0434(12) Uani 1 1 d . . . . .
H2 H 0.1979 0.5552 0.9792 0.052 Uiso 1 1 calc R U . . .
C3 C 0.2391(2) 0.6363(5) 0.9116(3) 0.0394(11) Uani 1 1 d . . . . .
C4 C 0.2898(3) 0.6261(6) 0.8954(4) 0.0549(15) Uani 1 1 d . . . . .
H4 H 0.2964 0.6832 0.8578 0.066 Uiso 1 1 calc R U . . .
C5 C 0.3305(3) 0.5310(7) 0.9351(4) 0.0552(16) Uani 1 1 d . . . . .
H5 H 0.3650 0.5239 0.9231 0.066 Uiso 1 1 calc R U . . .
C6 C 0.1913(3) 0.7314(7) 0.8695(3) 0.0544(15) Uani 1 1 d . . . . .
H6 H 0.1572 0.7328 0.8825 0.065 Uiso 1 1 calc R U . . .
C7 C 0.3795(2) 0.1533(6) 1.1573(3) 0.0443(13) Uani 1 1 d . . . . .
C8 C 0.3658(2) 0.1487(5) 0.9221(3) 0.0415(12) Uani 1 1 d . . . . .
C9 C 0.3693(2) 0.0646(6) 0.8551(3) 0.0424(12) Uani 1 1 d . . . . .
C10 C 0.3228(2) -0.0141(5) 0.8114(3) 0.0370(11) Uani 1 1 d . . . . .
H10 H 0.2887 -0.0160 0.8245 0.044 Uiso 1 1 calc R U . . .
C11 C 0.3248(2) -0.0916(5) 0.7476(3) 0.0392(11) Uani 1 1 d . . . . .
C12 C 0.3744(2) -0.0824(5) 0.7267(3) 0.0397(11) Uani 1 1 d . . . . .
C13 C 0.4198(3) 0.0671(9) 0.8372(4) 0.072(2) Uani 1 1 d . . . . .
H13 H 0.4531 0.1167 0.8693 0.087 Uiso 1 1 calc R U . . .
C14 C 0.4208(3) -0.0031(8) 0.7726(4) 0.067(2) Uani 1 1 d . . . . .
H14 H 0.4544 0.0027 0.7587 0.081 Uiso 1 1 calc R U . . .
C15A C 0.5102(6) 0.3162(12) 1.1173(8) 0.054(3) Uiso 0.5 1 d . . P B 1
C16A C 0.5657(5) 0.3648(12) 1.1605(7) 0.052(3) Uiso 0.5 1 d . . P B 1
C17A C 0.5703(5) 0.4896(14) 1.1914(7) 0.043(2) Uiso 0.5 1 d . . P B 1
C18A C 0.4620(6) 0.5106(14) 1.1300(9) 0.049(3) Uiso 0.5 1 d . . P B 1
C19A C 0.5189(7) 0.5650(15) 1.1784(9) 0.062(3) Uiso 0.5 1 d . . P B 1
C20A C 0.1278(6) 0.9521(14) 0.7389(8) 0.056(3) Uiso 0.5 1 d . . P A 1
N5B N 0.1291(5) 0.8543(11) 0.7839(7) 0.056(2) Uiso 0.5 1 d . . P A 2
C15B C 0.5065(4) 0.3512(10) 1.1591(6) 0.034(2) Uiso 0.5 1 d . . P B 2
C16B C 0.5581(4) 0.4178(10) 1.1997(5) 0.0297(19) Uiso 0.5 1 d . . P B 2
C17B C 0.5594(5) 0.5526(13) 1.1904(7) 0.041(2) Uiso 0.5 1 d . . P B 2
C19B C 0.5064(7) 0.6207(17) 1.1432(10) 0.075(4) Uiso 0.5 1 d . . P B 2
C20B C 0.1111(5) 0.8641(13) 0.7306(8) 0.051(3) Uiso 0.5 1 d . . P A 2
C0AA C 0.4569(7) 0.5456(18) 1.1034(11) 0.069(4) Uiso 0.5 1 d . . P B .
C1AA C 0.0717(4) 0.6468(10) 0.8968(7) 0.089(3) Uani 1 1 d . . . . .
O0AA O 0.0426(8) 0.696(2) 1.0176(11) 0.366(15) Uani 1 1 d D . . . .
C1 C 0.0765(6) 0.6288(13) 0.9623(10) 0.139(5) Uani 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 2.015(4) . ?
Zn1 O4 2.059(4) . ?
Zn1 N1 2.074(4) . ?
Zn1 N2 2.081(4) . ?
Zn1 O3 2.327(4) . ?
Zn1 O2 2.429(4) . ?
Zn1 C7 2.530(5) . ?
Zn1 C8 2.547(5) . ?
O1 C8 1.276(7) . ?
O2 C8 1.244(6) . ?
O3 C7 1.243(7) . ?
O4 C7 1.270(7) . ?
N1 C2AA 1.336(6) . ?
N1 C5 1.346(7) . ?
N2 C18A 1.210(14) . ?
N2 C15B 1.295(11) . ?
N2 C15A 1.466(14) . ?
N2 C0AA 1.498(18) . ?
N3 C11 1.396(8) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 C6 1.236(8) . ?
N4 N5A 1.364(10) . ?
N4 N5B 1.564(12) . ?
N5A C20A 0.966(14) . ?
C2AA C2 1.382(7) . ?
C2AA H2AA 0.9500 . ?
C2 C3 1.377(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(8) . ?
C3 C6 1.491(8) . ?
C4 C5 1.382(8) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.487(7) 6_556 ?
C8 C9 1.504(7) . ?
C9 C10 1.375(7) . ?
C9 C13 1.395(8) . ?
C10 C11 1.408(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.406(8) . ?
C12 C14 1.389(8) . ?
C12 C7 1.487(7) 6 ?
C13 C14 1.371(8) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15A C16A 1.385(17) . ?
C16A C17A 1.371(19) . ?
C17A C19A 1.419(19) . ?
C17A C20A 1.475(18) 8_566 ?
C18A C0AA 0.571(19) . ?
C18A C19A 1.452(19) . ?
C19A C0AA 1.63(2) . ?
C20A C17A 1.475(18) 8_465 ?
N5B C20B 0.901(14) . ?
C15B C16B 1.381(14) . ?
C16B C17B 1.379(16) . ?
C17B C19B 1.44(2) . ?
C17B C20B 1.472(17) 8_566 ?
C19B C0AA 1.39(2) . ?
C20B C17B 1.472(17) 8_465 ?
C1AA C1 1.156(17) . ?
O0AA C1 1.662(15) . ?

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 O4 145.83(18) . . ?
O1 Zn1 N1 106.06(16) . . ?
O4 Zn1 N1 95.80(15) . . ?
O1 Zn1 N2 96.05(17) . . ?
O4 Zn1 N2 104.95(16) . . ?
N1 Zn1 N2 101.82(16) . . ?
O1 Zn1 O3 95.07(16) . . ?
O4 Zn1 O3 59.22(15) . . ?
N1 Zn1 O3 154.76(15) . . ?
N2 Zn1 O3 89.25(16) . . ?
O1 Zn1 O2 58.44(14) . . ?
O4 Zn1 O2 96.41(14) . . ?
N1 Zn1 O2 90.01(15) . . ?
N2 Zn1 O2 154.22(15) . . ?
O3 Zn1 O2 89.44(14) . . ?
O1 Zn1 C7 121.69(19) . . ?
O4 Zn1 C7 29.96(18) . . ?
N1 Zn1 C7 125.71(18) . . ?
N2 Zn1 C7 97.56(17) . . ?
O3 Zn1 C7 29.27(17) . . ?
O2 Zn1 C7 93.77(15) . . ?
O1 Zn1 C8 29.67(16) . . ?
O4 Zn1 C8 121.54(17) . . ?
N1 Zn1 C8 100.23(17) . . ?
N2 Zn1 C8 125.49(17) . . ?
O3 Zn1 C8 91.26(16) . . ?
O2 Zn1 C8 28.82(15) . . ?
C7 Zn1 C8 108.47(18) . . ?
C8 O1 Zn1 99.0(3) . . ?
C8 O2 Zn1 80.9(3) . . ?
C7 O3 Zn1 84.5(3) . . ?
C7 O4 Zn1 96.0(3) . . ?
C2AA N1 C5 116.9(4) . . ?
C2AA N1 Zn1 118.7(3) . . ?
C5 N1 Zn1 124.1(3) . . ?
C18A N2 C15A 123.0(9) . . ?
C18A N2 C0AA 21.1(9) . . ?
C15B N2 C0AA 113.6(9) . . ?
C15A N2 C0AA 125.7(9) . . ?
C18A N2 Zn1 126.3(7) . . ?
C15B N2 Zn1 127.5(5) . . ?
C15A N2 Zn1 110.6(6) . . ?
C0AA N2 Zn1 118.1(7) . . ?
C11 N3 H3A 120.0 . . ?
C11 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C6 N4 N5A 123.6(6) . . ?
C6 N4 N5B 97.9(6) . . ?
C20A N5A N4 151.5(12) . . ?
N1 C2AA C2 122.6(5) . . ?
N1 C2AA H2AA 118.7 . . ?
C2 C2AA H2AA 118.7 . . ?
C3 C2 C2AA 120.2(5) . . ?
C3 C2 H2 119.9 . . ?
C2AA C2 H2 119.9 . . ?
C2 C3 C4 117.9(5) . . ?
C2 C3 C6 119.3(5) . . ?
C4 C3 C6 122.7(5) . . ?
C5 C4 C3 118.6(5) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 123.8(5) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
N4 C6 C3 122.1(6) . . ?
N4 C6 H6 118.9 . . ?
C3 C6 H6 118.9 . . ?
O3 C7 O4 120.3(5) . . ?
O3 C7 C12 120.1(5) . 6_556 ?
O4 C7 C12 119.6(5) . 6_556 ?
O3 C7 Zn1 66.3(3) . . ?
O4 C7 Zn1 54.0(3) . . ?
C12 C7 Zn1 173.3(4) 6_556 . ?
O2 C8 O1 121.5(5) . . ?
O2 C8 C9 120.6(5) . . ?
O1 C8 C9 117.8(5) . . ?
O2 C8 Zn1 70.3(3) . . ?
O1 C8 Zn1 51.4(2) . . ?
C9 C8 Zn1 168.6(4) . . ?
C10 C9 C13 120.0(5) . . ?
C10 C9 C8 120.3(5) . . ?
C13 C9 C8 119.7(5) . . ?
C9 C10 C11 121.2(5) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
N3 C11 C12 123.9(5) . . ?
N3 C11 C10 117.6(5) . . ?
C12 C11 C10 118.5(5) . . ?
C14 C12 C11 118.8(5) . . ?
C14 C12 C7 118.1(5) . 6 ?
C11 C12 C7 123.1(5) . 6 ?
C14 C13 C9 119.0(6) . . ?
C14 C13 H13 120.5 . . ?
C9 C13 H13 120.5 . . ?
C13 C14 C12 122.3(6) . . ?
C13 C14 H14 118.8 . . ?
C12 C14 H14 118.8 . . ?
C16A C15A N2 119.6(11) . . ?
C17A C16A C15A 118.1(12) . . ?
C16A C17A C19A 119.9(12) . . ?
C16A C17A C20A 121.4(12) . 8_566 ?
C19A C17A C20A 118.8(13) . 8_566 ?
C0AA C18A N2 109(3) . . ?
C0AA C18A C19A 97(3) . . ?
N2 C18A C19A 119.6(12) . . ?
C17A C19A C18A 119.5(12) . . ?
C17A C19A C0AA 124.9(12) . . ?
C18A C19A C0AA 20.4(7) . . ?
N5A C20A C17A 153.5(14) . 8_465 ?
C20B N5B N4 118.5(13) . . ?
N2 C15B C16B 127.7(9) . . ?
C15B C16B C17B 118.6(9) . . ?
C16B C17B C19B 119.4(11) . . ?
C16B C17B C20B 124.3(11) . 8_566 ?
C19B C17B C20B 116.1(12) . 8_566 ?
C0AA C19B C17B 117.9(15) . . ?
N5B C20B C17B 125.3(14) . 8_465 ?
C18A C0AA N2 50(2) . . ?
C19B C0AA N2 121.4(14) . . ?
C18A C0AA C19A 62(2) . . ?
N2 C0AA C19A 94.9(11) . . ?
C1AA C1 O0AA 131.6(15) . . ?

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
C6 N4 N5A C20A -127(2) . . . . ?
C5 N1 C2AA C2 -0.6(8) . . . . ?
Zn1 N1 C2AA C2 -175.0(4) . . . . ?
N1 C2AA C2 C3 0.0(8) . . . . ?
C2AA C2 C3 C4 0.2(8) . . . . ?
C2AA C2 C3 C6 177.7(5) . . . . ?
C2 C3 C4 C5 0.2(9) . . . . ?
C6 C3 C4 C5 -177.2(6) . . . . ?
C2AA N1 C5 C4 1.0(9) . . . . ?
Zn1 N1 C5 C4 175.1(5) . . . . ?
C3 C4 C5 N1 -0.8(10) . . . . ?
N5A N4 C6 C3 -172.6(6) . . . . ?
N5B N4 C6 C3 167.6(6) . . . . ?
C2 C3 C6 N4 -178.5(6) . . . . ?
C4 C3 C6 N4 -1.1(10) . . . . ?
Zn1 O3 C7 O4 1.5(5) . . . . ?
Zn1 O3 C7 C12 -177.6(4) . . . 6_556 ?
Zn1 O4 C7 O3 -1.7(5) . . . . ?
Zn1 O4 C7 C12 177.4(4) . . . 6_556 ?
Zn1 O2 C8 O1 -4.2(5) . . . . ?
Zn1 O2 C8 C9 176.6(5) . . . . ?
Zn1 O1 C8 O2 5.1(6) . . . . ?
Zn1 O1 C8 C9 -175.7(4) . . . . ?
O2 C8 C9 C10 2.5(8) . . . . ?
O1 C8 C9 C10 -176.7(5) . . . . ?
Zn1 C8 C9 C10 166.0(17) . . . . ?
O2 C8 C9 C13 -177.8(6) . . . . ?
O1 C8 C9 C13 2.9(9) . . . . ?
Zn1 C8 C9 C13 -14(2) . . . . ?
C13 C9 C10 C11 -0.8(9) . . . . ?
C8 C9 C10 C11 178.8(5) . . . . ?
C9 C10 C11 N3 174.9(5) . . . . ?
C9 C10 C11 C12 -3.1(8) . . . . ?
N3 C11 C12 C14 -174.2(6) . . . . ?
C10 C11 C12 C14 3.6(8) . . . . ?
N3 C11 C12 C7 6.1(8) . . . 6 ?
C10 C11 C12 C7 -176.0(5) . . . 6 ?
C10 C9 C13 C14 4.1(11) . . . . ?
C8 C9 C13 C14 -175.6(7) . . . . ?
C9 C13 C14 C12 -3.5(13) . . . . ?
C11 C12 C14 C13 -0.4(11) . . . . ?
C7 C12 C14 C13 179.3(7) 6 . . . ?
C18A N2 C15A C16A 4.0(17) . . . . ?
C0AA N2 C15A C16A 29.4(17) . . . . ?
Zn1 N2 C15A C16A -177.8(9) . . . . ?
N2 C15A C16A C17A -0.2(18) . . . . ?
C15A C16A C17A C19A -0.3(19) . . . . ?
C15A C16A C17A C20A 179.2(11) . . . 8_566 ?
C15A N2 C18A C0AA 104(3) . . . . ?
Zn1 N2 C18A C0AA -74(3) . . . . ?
C15A N2 C18A C19A -6.5(18) . . . . ?
C0AA N2 C18A C19A -111(3) . . . . ?
Zn1 N2 C18A C19A 175.6(9) . . . . ?
C16A C17A C19A C18A -2(2) . . . . ?
C20A C17A C19A C18A 178.3(12) 8_566 . . . ?
C16A C17A C19A C0AA -25(2) . . . . ?
C20A C17A C19A C0AA 155.1(14) 8_566 . . . ?
C0AA C18A C19A C17A -111(3) . . . . ?
N2 C18A C19A C17A 6(2) . . . . ?
N2 C18A C19A C0AA 117(3) . . . . ?
N4 N5A C20A C17A 129(3) . . . 8_465 ?
C6 N4 N5B C20B -139.1(15) . . . . ?
C0AA N2 C15B C16B -13.2(14) . . . . ?
Zn1 N2 C15B C16B 178.1(7) . . . . ?
N2 C15B C16B C17B 6.2(16) . . . . ?
C15B C16B C17B C19B 4.1(17) . . . . ?
C15B C16B C17B C20B 179.4(10) . . . 8_566 ?
C16B C17B C19B C0AA -5(2) . . . . ?
C20B C17B C19B C0AA 179.1(14) 8_566 . . . ?
N4 N5B C20B C17B -157.2(11) . . . 8_465 ?
C19A C18A C0AA N2 125(2) . . . . ?
N2 C18A C0AA C19A -125(2) . . . . ?
C17B C19B C0AA N2 -2(2) . . . . ?
C15A N2 C0AA C18A -90(3) . . . . ?
Zn1 N2 C0AA C18A 119(3) . . . . ?
C15B N2 C0AA C19B 11.0(19) . . . . ?
Zn1 N2 C0AA C19B -179.2(12) . . . . ?
C18A N2 C0AA C19A 47(3) . . . . ?
C15A N2 C0AA C19A -43.5(14) . . . . ?
Zn1 N2 C0AA C19A 165.6(7) . . . . ?
C17A C19A C0AA C18A 81(3) . . . . ?
C17A C19A C0AA N2 42.2(18) . . . . ?
C18A C19A C0AA N2 -39(2) . . . . ?

_refine_diff_density_max         1.435
_refine_diff_density_min         -1.668
_refine_diff_density_rms         0.110

_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_COMPOUND_4
_database_code_depnum_ccdc_archive 'CCDC 1440848'
_audit_update_record             
;
2016-03-21 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H46 N12 O10 Zn3, 2(Cl O4), 2(C O)'
_chemical_formula_sum            'C50 H46 Cl2 N12 O20 Zn3'
_chemical_formula_weight         1402.06

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   10.6476(13)
_cell_length_b                   19.578(2)
_cell_length_c                   15.1746(17)
_cell_angle_alpha                90
_cell_angle_beta                 107.808(4)
_cell_angle_gamma                90
_cell_volume                     3011.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9478
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      25.06

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_F_000             1428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    1.356
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.581
_exptl_absorpt_correction_T_max  0.712
_exptl_absorpt_process_details   MULTI-SCAN
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            98195
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.752
_diffrn_reflns_theta_max         25.087
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             5366
_reflns_number_gt                4876
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0100P)²+5.8684P] 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         5366
_refine_ls_number_parameters     394
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0840
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.164
_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 -0.00922(3) 0.19335(2) 0.47475(2) 0.02943(10) Uani 1 1 d . . . . .
Zn2 Zn 0.0000 0.0000 0.5000 0.02701(12) Uani 1 2 d S . P . .
O2 O 0.14667(19) 0.16263(11) 0.43780(14) 0.0349(5) Uani 1 1 d . . . . .
O4 O 0.81402(19) 0.19466(11) 0.51091(14) 0.0350(5) Uani 1 1 d . . . . .
O5 O 0.89966(18) 0.09457(11) 0.50432(14) 0.0324(5) Uani 1 1 d . . . . .
O3 O 0.1484(2) 0.04945(12) 0.45752(15) 0.0400(5) Uani 1 1 d . . . . .
O1 O 0.0100(3) 0.30039(12) 0.46593(17) 0.0537(6) Uani 1 1 d . . . . .
N2 N 0.4590(3) 0.20503(18) 0.92595(18) 0.0548(8) Uani 1 1 d . . . . .
C17 C -0.1686(3) 0.1550(2) 0.1734(2) 0.0468(9) Uani 1 1 d . . . . .
H17 H -0.1382 0.1314 0.1307 0.056 Uiso 1 1 calc R U . . .
N3 N 0.5167(3) 0.20985(18) 1.02247(18) 0.0531(8) Uani 1 1 d . . . . .
N6 N -0.4715(3) 0.00230(18) 0.04874(19) 0.0554(8) Uani 1 1 d . . . . .
N4 N -0.1317(2) 0.18956(14) 0.33015(17) 0.0353(6) Uani 1 1 d . . . . .
C16 C -0.2882(3) 0.18805(18) 0.1455(2) 0.0392(7) Uani 1 1 d . . . . .
N5 N -0.1168(2) -0.01152(13) 0.35774(16) 0.0313(6) Uani 1 1 d . . . . .
N1 N 0.1098(2) 0.19951(13) 0.61754(16) 0.0338(6) Uani 1 1 d . . . . .
C12 C 0.3360(3) 0.20884(18) 0.9013(2) 0.0430(8) Uani 1 1 d . . . . .
H12 H 0.2926 0.2140 0.9456 0.052 Uiso 1 1 calc R U . . .
C22 C 0.5647(3) 0.10966(18) 0.4598(2) 0.0400(8) Uani 1 1 d . . . . .
H22A H 0.5634 0.1551 0.4342 0.048 Uiso 1 1 calc R U . . .
H22B H 0.5638 0.0770 0.4115 0.048 Uiso 1 1 calc R U . . .
C23 C 0.6919(3) 0.10054(18) 0.5399(2) 0.0401(8) Uani 1 1 d . . . . .
H23A H 0.6821 0.1223 0.5949 0.048 Uiso 1 1 calc R U . . .
H23B H 0.7075 0.0522 0.5530 0.048 Uiso 1 1 calc R U . . .
C11 C 0.0545(3) 0.2087(2) 0.6836(2) 0.0544(10) Uani 1 1 d . . . . .
H11 H -0.0368 0.2131 0.6668 0.065 Uiso 1 1 calc R U . . .
C21 C 0.4416(3) 0.09977(18) 0.4890(2) 0.0398(7) Uani 1 1 d . . . . .
H21A H 0.4359 0.1362 0.5309 0.048 Uiso 1 1 calc R U . . .
H21B H 0.4480 0.0568 0.5220 0.048 Uiso 1 1 calc R U . . .
C10 C 0.1256(3) 0.2120(2) 0.7761(2) 0.0606(12) Uani 1 1 d . . . . .
H10 H 0.0823 0.2188 0.8201 0.073 Uiso 1 1 calc R U . . .
C1 C -0.0647(3) -0.02427(18) 0.2903(2) 0.0415(8) Uani 1 1 d . . . . .
H1A H 0.0258 -0.0316 0.3058 0.050 Uiso 1 1 calc R U . . .
C9 C 0.2599(3) 0.20524(17) 0.8032(2) 0.0365(7) Uani 1 1 d . . . . .
C19 C 0.1929(3) 0.10362(16) 0.43589(18) 0.0297(6) Uani 1 1 d . . . . .
C4 C -0.2735(3) -0.01553(17) 0.1728(2) 0.0408(8) Uani 1 1 d . . . . .
C24 C 0.8086(3) 0.13113(16) 0.51769(18) 0.0294(6) Uani 1 1 d . . . . .
C3 C -0.3284(3) -0.0037(2) 0.2431(2) 0.0472(9) Uani 1 1 d . . . . .
H3 H -0.4187 0.0033 0.2296 0.057 Uiso 1 1 calc R U . . .
C18 C -0.0942(3) 0.15711(19) 0.2653(2) 0.0448(8) Uani 1 1 d . . . . .
H18 H -0.0134 0.1346 0.2831 0.054 Uiso 1 1 calc R U . . .
C5 C -0.1392(3) -0.0271(2) 0.1980(2) 0.0497(9) Uani 1 1 d . . . . .
H5 H -0.0990 -0.0369 0.1530 0.060 Uiso 1 1 calc R U . . .
C20 C 0.3165(3) 0.09957(17) 0.4056(2) 0.0352(7) Uani 1 1 d . . . . .
H20A H 0.3185 0.1382 0.3660 0.042 Uiso 1 1 calc R U . . .
H20B H 0.3139 0.0581 0.3700 0.042 Uiso 1 1 calc R U . . .
C6 C -0.3526(4) -0.0158(2) 0.0741(2) 0.0519(9) Uani 1 1 d . . . . .
H6 H -0.3137 -0.0296 0.0299 0.062 Uiso 1 1 calc R U . . .
C15 C -0.3290(3) 0.2214(2) 0.2120(2) 0.0518(9) Uani 1 1 d . . . . .
H15 H -0.4099 0.2437 0.1958 0.062 Uiso 1 1 calc R U . . .
C14 C -0.2489(3) 0.2213(2) 0.3028(2) 0.0470(9) Uani 1 1 d . . . . .
H14 H -0.2774 0.2443 0.3468 0.056 Uiso 1 1 calc R U . . .
C8 C 0.3179(3) 0.1936(2) 0.7354(2) 0.0614(12) Uani 1 1 d . . . . .
H8 H 0.4085 0.1869 0.7508 0.074 Uiso 1 1 calc R U . . .
C13 C 0.6327(3) 0.18739(19) 1.0474(2) 0.0462(8) Uani 1 1 d . . . . .
H13 H 0.6689 0.1702 1.0034 0.055 Uiso 1 1 calc R U . . .
C2 C -0.2478(3) -0.00251(19) 0.3334(2) 0.0432(8) Uani 1 1 d . . . . .
H2 H -0.2862 0.0050 0.3799 0.052 Uiso 1 1 calc R U . . .
C7 C 0.2406(3) 0.1920(3) 0.6445(2) 0.0624(12) Uani 1 1 d . . . . .
H7 H 0.2817 0.1854 0.5992 0.075 Uiso 1 1 calc R U . . .
Cl1 Cl 0.77196(14) 0.42675(7) 0.32883(10) 0.0869(4) Uani 1 1 d . . . . .
O8 O 0.7981(10) 0.4879(3) 0.2999(6) 0.248(4) Uani 1 1 d . . . . .
O9 O 0.7920(8) 0.4203(5) 0.4180(4) 0.266(5) Uani 1 1 d . . . . .
O7 O 0.8548(4) 0.3804(2) 0.3016(4) 0.1310(17) Uani 1 1 d . . . . .
O6 O 0.6419(6) 0.4139(6) 0.2836(6) 0.288(5) Uani 1 1 d . . . . .
O10 O 0.1665(8) 0.1165(3) 0.0964(5) 0.220(4) Uani 1 1 d . . . . .
C25 C 0.3362(11) 0.1251(4) 0.1451(5) 0.159(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 O2 2.000(2) . ?
Zn1 O1 2.114(2) . ?
Zn1 O4 2.116(2) 1_455 ?
Zn1 N1 2.153(2) . ?
Zn1 N4 2.184(2) . ?
Zn1 O5 2.269(2) 1_455 ?
Zn1 C24 2.539(3) 1_455 ?
Zn2 O3 2.115(2) 3_556 ?
Zn2 O3 2.115(2) . ?
Zn2 N5 2.148(2) 3_556 ?
Zn2 N5 2.148(2) . ?
Zn2 O5 2.149(2) 1_455 ?
Zn2 O5 2.149(2) 3_656 ?
O2 C19 1.259(4) . ?
O4 C24 1.251(4) . ?
O4 Zn1 2.116(2) 1_655 ?
O5 C24 1.271(3) . ?
O5 Zn2 2.149(2) 1_655 ?
O5 Zn1 2.269(2) 1_655 ?
O3 C19 1.246(4) . ?
N2 C12 1.250(4) . ?
N2 N3 1.407(4) . ?
C17 C16 1.375(5) . ?
C17 C18 1.378(4) . ?
C17 H17 0.9300 . ?
N3 C13 1.256(4) . ?
N6 C6 1.257(5) . ?
N6 N6 1.420(5) 3_455 ?
N4 C18 1.330(4) . ?
N4 C14 1.342(4) . ?
C16 C15 1.378(5) . ?
C16 C13 1.470(4) 1_454 ?
N5 C1 1.329(4) . ?
N5 C2 1.341(4) . ?
N1 C11 1.320(4) . ?
N1 C7 1.334(4) . ?
C12 C9 1.464(4) . ?
C12 H12 0.9300 . ?
C22 C21 1.520(4) . ?
C22 C23 1.529(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.507(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C11 C10 1.378(5) . ?
C11 H11 0.9300 . ?
C21 C20 1.531(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C10 C9 1.368(5) . ?
C10 H10 0.9300 . ?
C1 C5 1.384(4) . ?
C1 H1A 0.9300 . ?
C9 C8 1.371(5) . ?
C19 C20 1.523(4) . ?
C4 C5 1.381(5) . ?
C4 C3 1.384(5) . ?
C4 C6 1.477(4) . ?
C24 Zn1 2.539(3) 1_655 ?
C3 C2 1.376(4) . ?
C3 H3 0.9300 . ?
C18 H18 0.9300 . ?
C5 H5 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C6 H6 0.9300 . ?
C15 C14 1.381(4) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C8 C7 1.374(5) . ?
C8 H8 0.9300 . ?
C13 C16 1.470(4) 1_656 ?
C13 H13 0.9300 . ?
C2 H2 0.9300 . ?
C7 H7 0.9300 . ?
Cl1 O9 1.310(5) . ?
Cl1 O8 1.333(6) . ?
Cl1 O6 1.368(7) . ?
Cl1 O7 1.413(4) . ?
O10 C25 1.739(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
O2 Zn1 O1 100.11(10) . . ?
O2 Zn1 O4 163.09(9) . 1_455 ?
O1 Zn1 O4 96.63(9) . 1_455 ?
O2 Zn1 N1 90.89(9) . . ?
O1 Zn1 N1 88.25(10) . . ?
O4 Zn1 N1 92.00(9) 1_455 . ?
O2 Zn1 N4 89.99(9) . . ?
O1 Zn1 N4 90.55(10) . . ?
O4 Zn1 N4 87.47(9) 1_455 . ?
N1 Zn1 N4 178.63(10) . . ?
O2 Zn1 O5 103.94(8) . 1_455 ?
O1 Zn1 O5 155.92(9) . 1_455 ?
O4 Zn1 O5 59.40(8) 1_455 1_455 ?
N1 Zn1 O5 90.25(9) . 1_455 ?
N4 Zn1 O5 90.56(9) . 1_455 ?
O2 Zn1 C24 133.83(9) . 1_455 ?
O1 Zn1 C24 126.04(10) . 1_455 ?
O4 Zn1 C24 29.42(9) 1_455 1_455 ?
N1 Zn1 C24 91.69(9) . 1_455 ?
N4 Zn1 C24 88.47(9) . 1_455 ?
O5 Zn1 C24 29.98(8) 1_455 1_455 ?
O3 Zn2 O3 180.0 3_556 . ?
O3 Zn2 N5 89.93(9) 3_556 3_556 ?
O3 Zn2 N5 90.07(9) . 3_556 ?
O3 Zn2 N5 90.07(9) 3_556 . ?
O3 Zn2 N5 89.93(9) . . ?
N5 Zn2 N5 180.0 3_556 . ?
O3 Zn2 O5 87.72(8) 3_556 1_455 ?
O3 Zn2 O5 92.28(8) . 1_455 ?
N5 Zn2 O5 91.11(8) 3_556 1_455 ?
N5 Zn2 O5 88.89(8) . 1_455 ?
O3 Zn2 O5 92.28(8) 3_556 3_656 ?
O3 Zn2 O5 87.72(8) . 3_656 ?
N5 Zn2 O5 88.89(8) 3_556 3_656 ?
N5 Zn2 O5 91.11(8) . 3_656 ?
O5 Zn2 O5 180.00(11) 1_455 3_656 ?
C19 O2 Zn1 130.23(19) . . ?
C24 O4 Zn1 94.39(17) . 1_655 ?
C24 O5 Zn2 154.3(2) . 1_655 ?
C24 O5 Zn1 86.85(17) . 1_655 ?
Zn2 O5 Zn1 118.79(8) 1_655 1_655 ?
C19 O3 Zn2 148.2(2) . . ?
C12 N2 N3 113.0(3) . . ?
C16 C17 C18 119.2(3) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C13 N3 N2 111.4(3) . . ?
C6 N6 N6 111.8(4) . 3_455 ?
C18 N4 C14 117.0(3) . . ?
C18 N4 Zn1 122.5(2) . . ?
C14 N4 Zn1 120.5(2) . . ?
C17 C16 C15 117.9(3) . . ?
C17 C16 C13 119.8(3) . 1_454 ?
C15 C16 C13 122.3(3) . 1_454 ?
C1 N5 C2 117.2(3) . . ?
C1 N5 Zn2 122.9(2) . . ?
C2 N5 Zn2 119.8(2) . . ?
C11 N1 C7 116.6(3) . . ?
C11 N1 Zn1 120.6(2) . . ?
C7 N1 Zn1 122.7(2) . . ?
N2 C12 C9 120.3(3) . . ?
N2 C12 H12 119.8 . . ?
C9 C12 H12 119.8 . . ?
C21 C22 C23 112.7(3) . . ?
C21 C22 H22A 109.0 . . ?
C23 C22 H22A 109.0 . . ?
C21 C22 H22B 109.0 . . ?
C23 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C24 C23 C22 111.4(3) . . ?
C24 C23 H23A 109.3 . . ?
C22 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
C22 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
N1 C11 C10 123.1(3) . . ?
N1 C11 H11 118.4 . . ?
C10 C11 H11 118.4 . . ?
C22 C21 C20 111.7(3) . . ?
C22 C21 H21A 109.3 . . ?
C20 C21 H21A 109.3 . . ?
C22 C21 H21B 109.3 . . ?
C20 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
N5 C1 C5 122.8(3) . . ?
N5 C1 H1A 118.6 . . ?
C5 C1 H1A 118.6 . . ?
C10 C9 C8 117.4(3) . . ?
C10 C9 C12 120.3(3) . . ?
C8 C9 C12 122.3(3) . . ?
O3 C19 O2 126.3(3) . . ?
O3 C19 C20 117.9(3) . . ?
O2 C19 C20 115.8(3) . . ?
C5 C4 C3 117.4(3) . . ?
C5 C4 C6 120.0(3) . . ?
C3 C4 C6 122.6(3) . . ?
O4 C24 O5 119.3(3) . . ?
O4 C24 C23 118.4(3) . . ?
O5 C24 C23 122.2(3) . . ?
O4 C24 Zn1 56.18(14) . 1_655 ?
O5 C24 Zn1 63.17(15) . 1_655 ?
C23 C24 Zn1 174.2(2) . 1_655 ?
C2 C3 C4 119.2(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
N4 C18 C17 123.6(3) . . ?
N4 C18 H18 118.2 . . ?
C17 C18 H18 118.2 . . ?
C4 C5 C1 119.9(3) . . ?
C4 C5 H5 120.1 . . ?
C1 C5 H5 120.1 . . ?
C19 C20 C21 111.3(2) . . ?
C19 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
N6 C6 C4 121.2(3) . . ?
N6 C6 H6 119.4 . . ?
C4 C6 H6 119.4 . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
N4 C14 C15 122.7(3) . . ?
N4 C14 H14 118.6 . . ?
C15 C14 H14 118.6 . . ?
C9 C8 C7 119.2(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
N3 C13 C16 120.5(3) . 1_656 ?
N3 C13 H13 119.7 . . ?
C16 C13 H13 119.7 1_656 . ?
N5 C2 C3 123.5(3) . . ?
N5 C2 H2 118.2 . . ?
C3 C2 H2 118.2 . . ?
N1 C7 C8 123.6(3) . . ?
N1 C7 H7 118.2 . . ?
C8 C7 H7 118.2 . . ?
O9 Cl1 O8 116.3(6) . . ?
O9 Cl1 O6 108.7(5) . . ?
O8 Cl1 O6 106.3(6) . . ?
O9 Cl1 O7 108.7(4) . . ?
O8 Cl1 O7 105.6(4) . . ?
O6 Cl1 O7 111.3(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
C12 N2 N3 C13 161.6(4) . . . . ?
C18 C17 C16 C15 -0.8(6) . . . . ?
C18 C17 C16 C13 178.7(3) . . . 1_454 ?
N3 N2 C12 C9 179.6(3) . . . . ?
C21 C22 C23 C24 -162.4(3) . . . . ?
C7 N1 C11 C10 1.3(6) . . . . ?
Zn1 N1 C11 C10 179.0(3) . . . . ?
C23 C22 C21 C20 -172.3(3) . . . . ?
N1 C11 C10 C9 -0.4(7) . . . . ?
C2 N5 C1 C5 1.2(5) . . . . ?
Zn2 N5 C1 C5 -175.6(3) . . . . ?
C11 C10 C9 C8 -1.6(6) . . . . ?
C11 C10 C9 C12 179.9(4) . . . . ?
N2 C12 C9 C10 -177.5(4) . . . . ?
N2 C12 C9 C8 4.0(6) . . . . ?
Zn2 O3 C19 O2 3.9(6) . . . . ?
Zn2 O3 C19 C20 -177.2(3) . . . . ?
Zn1 O2 C19 O3 0.2(4) . . . . ?
Zn1 O2 C19 C20 -178.62(18) . . . . ?
Zn1 O4 C24 O5 1.4(3) 1_655 . . . ?
Zn1 O4 C24 C23 -177.5(2) 1_655 . . . ?
Zn2 O5 C24 O4 175.6(3) 1_655 . . . ?
Zn1 O5 C24 O4 -1.3(2) 1_655 . . . ?
Zn2 O5 C24 C23 -5.5(6) 1_655 . . . ?
Zn1 O5 C24 C23 177.6(2) 1_655 . . . ?
Zn2 O5 C24 Zn1 176.9(4) 1_655 . . 1_655 ?
C22 C23 C24 O4 68.3(4) . . . . ?
C22 C23 C24 O5 -110.6(3) . . . . ?
C5 C4 C3 C2 1.5(6) . . . . ?
C6 C4 C3 C2 -178.3(4) . . . . ?
C14 N4 C18 C17 0.3(5) . . . . ?
Zn1 N4 C18 C17 -178.8(3) . . . . ?
C16 C17 C18 N4 0.2(6) . . . . ?
C3 C4 C5 C1 -2.2(6) . . . . ?
C6 C4 C5 C1 177.6(4) . . . . ?
N5 C1 C5 C4 0.9(6) . . . . ?
O3 C19 C20 C21 -84.3(3) . . . . ?
O2 C19 C20 C21 94.6(3) . . . . ?
C22 C21 C20 C19 -168.9(3) . . . . ?
N6 N6 C6 C4 -179.7(4) 3_455 . . . ?
C5 C4 C6 N6 -171.7(4) . . . . ?
C3 C4 C6 N6 8.1(6) . . . . ?
C17 C16 C15 C14 0.9(6) . . . . ?
C13 C16 C15 C14 -178.6(4) 1_454 . . . ?
C18 N4 C14 C15 -0.2(6) . . . . ?
Zn1 N4 C14 C15 178.9(3) . . . . ?
C16 C15 C14 N4 -0.4(6) . . . . ?
C10 C9 C8 C7 2.6(7) . . . . ?
C12 C9 C8 C7 -178.9(4) . . . . ?
N2 N3 C13 C16 179.6(3) . . . 1_656 ?
C1 N5 C2 C3 -2.1(5) . . . . ?
Zn2 N5 C2 C3 174.8(3) . . . . ?
C4 C3 C2 N5 0.7(6) . . . . ?
C11 N1 C7 C8 -0.2(7) . . . . ?
Zn1 N1 C7 C8 -177.9(4) . . . . ?
C9 C8 C7 N1 -1.8(7) . . . . ?

_refine_diff_density_max         0.714
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.069

_shelxl_version_number           2014/6

