# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

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

data_230Ext_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1517763'
_audit_update_record             
;
2017-01-30 deposited with the CCDC.
2017-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 Cd N2 O6'
_chemical_formula_weight         570.85

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'
Cd Cd -0.8075 1.2024 '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                   9.4482(9)
_cell_length_b                   10.0882(9)
_cell_length_c                   14.7102(13)
_cell_angle_alpha                72.942(3)
_cell_angle_beta                 82.840(3)
_cell_angle_gamma                64.910(3)
_cell_volume                     1213.95(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      28.46

_exptl_crystal_description       rectengular
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.670
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.944
_shelx_estimated_absorpt_T_min   0.571
_shelx_estimated_absorpt_T_max   0.798
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'φ and ω scans'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16165
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.380
_diffrn_reflns_theta_max         28.474
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             5903
_reflns_number_gt                5326
_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-2014/7 (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)+(0.0639P)²+3.5814P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.037(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5903
_refine_ls_number_parameters     333
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1518
_refine_ls_wR_factor_gt          0.1419
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.134
_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
C1 C 0.3208(6) 0.3941(7) 0.3412(4) 0.0521(12) Uani 1 1 d . . . . .
H1 H 0.3716 0.4226 0.3772 0.063 Uiso 1 1 calc R U . . .
Cd1 Cd 0.25006(3) 0.22639(3) 0.55266(2) 0.03337(16) Uani 1 1 d . . . . .
N1 N 0.2517(5) 0.3024(5) 0.3861(4) 0.0466(9) Uani 1 1 d . . . . .
O1 O 0.5166(4) 0.1334(4) 0.5717(3) 0.0451(7) Uani 1 1 d D . . . .
C2 C 0.3207(7) 0.4492(7) 0.2432(4) 0.0563(13) Uani 1 1 d . . . . .
H2 H 0.3660 0.5172 0.2145 0.068 Uiso 1 1 calc R U . . .
N2 N 0.2514(5) 0.1460(5) 0.7189(2) 0.0415(8) Uani 1 1 d . . . . .
O2 O -0.0165(4) 0.3070(4) 0.5697(3) 0.0449(7) Uani 1 1 d D . . . .
C3 C 0.2520(6) 0.4015(7) 0.1887(4) 0.0487(11) Uani 1 1 d . . . . .
O3 O 0.2329(4) 0.4592(3) 0.5535(3) 0.0419(7) Uani 1 1 d . . . . .
C4 C 0.1856(7) 0.3013(7) 0.2370(4) 0.0596(14) Uani 1 1 d . . . . .
H4 H 0.1411 0.2638 0.2031 0.072 Uiso 1 1 calc R U . . .
O4 O 0.4600(5) 0.3967(4) 0.6208(4) 0.0702(13) Uani 1 1 d . . . . .
C5 C 0.1852(6) 0.2566(6) 0.3360(4) 0.0506(12) Uani 1 1 d . . . . .
H5 H 0.1366 0.1926 0.3673 0.061 Uiso 1 1 calc R U . . .
O5 O 0.2634(4) 0.9967(3) 0.5471(3) 0.0416(7) Uani 1 1 d . . . . .
C6 C 0.2516(6) 0.4585(7) 0.0822(4) 0.0553(13) Uani 1 1 d . . . . .
O6 O 0.0356(5) 1.0043(4) 0.6153(3) 0.0613(11) Uani 1 1 d . . . . .
C7 C 0.2820(19) 0.5802(16) 0.0371(6) 0.150(6) Uani 1 1 d . . . . .
H7 H 0.3034 0.6321 0.0726 0.180 Uiso 1 1 calc R U . . .
C8 C 0.282(2) 0.6308(18) -0.0630(7) 0.170(7) Uani 1 1 d . . . . .
H8 H 0.3060 0.7142 -0.0917 0.204 Uiso 1 1 calc R U . . .
C9 C 0.2504(10) 0.5658(10) -0.1160(5) 0.081(2) Uani 1 1 d . . . . .
H9 H 0.2508 0.5996 -0.1820 0.097 Uiso 1 1 calc R U . . .
C10 C 0.217(2) 0.4487(18) -0.0715(7) 0.174(7) Uani 1 1 d . . . . .
H10 H 0.1903 0.4010 -0.1075 0.209 Uiso 1 1 calc R U . . .
C11 C 0.221(2) 0.3932(16) 0.0266(7) 0.157(6) Uani 1 1 d . . . . .
H11 H 0.2007 0.3072 0.0539 0.189 Uiso 1 1 calc R U . . .
C12 C 0.1386(8) 0.2227(8) 0.7696(4) 0.0615(14) Uani 1 1 d . . . . .
H12 H 0.0579 0.3115 0.7380 0.074 Uiso 1 1 calc R U . . .
C13 C 0.1350(9) 0.1770(10) 0.8675(5) 0.0749(19) Uani 1 1 d . . . . .
H13 H 0.0539 0.2361 0.9004 0.090 Uiso 1 1 calc R U . . .
C14 C 0.2512(8) 0.0440(9) 0.9175(4) 0.0654(17) Uani 1 1 d . . . . .
C15 C 0.3674(9) -0.0374(9) 0.8630(4) 0.0734(18) Uani 1 1 d . . . . .
H15 H 0.4474 -0.1289 0.8922 0.088 Uiso 1 1 calc R U . . .
C16 C 0.3637(8) 0.0180(8) 0.7652(4) 0.0618(14) Uani 1 1 d . . . . .
H16 H 0.4439 -0.0372 0.7301 0.074 Uiso 1 1 calc R U . . .
C17 C 0.2501(11) -0.0115(11) 1.0233(4) 0.083(2) Uani 1 1 d . . . . .
C18 C 0.1139(13) 0.0383(13) 1.0742(5) 0.102(3) Uani 1 1 d . . . . .
H18 H 0.0211 0.1059 1.0419 0.123 Uiso 1 1 calc R U . . .
C19 C 0.1131(15) -0.0113(15) 1.1733(5) 0.117(4) Uani 1 1 d . . . . .
H19 H 0.0208 0.0250 1.2068 0.140 Uiso 1 1 calc R U . . .
C20 C 0.2483(14) -0.1134(14) 1.2212(5) 0.116(4) Uani 1 1 d . . . . .
H20 H 0.2475 -0.1473 1.2872 0.140 Uiso 1 1 calc R U . . .
C21 C 0.3857(15) -0.1660(14) 1.1719(5) 0.121(4) Uani 1 1 d . . . . .
H21 H 0.4775 -0.2352 1.2047 0.145 Uiso 1 1 calc R U . . .
C22 C 0.3875(13) -0.1153(12) 1.0720(5) 0.101(3) Uani 1 1 d . . . . .
H22 H 0.4801 -0.1510 1.0387 0.122 Uiso 1 1 calc R U . . .
C23 C 0.3283(5) 0.4868(4) 0.5897(3) 0.0390(9) Uani 1 1 d . . . . .
C24 C 0.2722(6) 0.6466(5) 0.5925(3) 0.0405(9) Uani 1 1 d . . . . .
C25 C 0.2223(6) 0.7760(5) 0.5909(3) 0.0403(9) Uani 1 1 d . . . . .
C26 C 0.1667(5) 0.9397(5) 0.5850(3) 0.0370(8) Uani 1 1 d . . . . .
H1B H 0.533(11) 0.213(8) 0.589(7) 0.11(3) Uiso 1 1 d D . . . .
H1A H 0.601(7) 0.091(9) 0.527(5) 0.10(3) Uiso 1 1 d D . . . .
H2B H -0.094(8) 0.394(6) 0.524(5) 0.10(3) Uiso 1 1 d D . . . .
H3A H -0.048(10) 0.221(7) 0.582(6) 0.11(3) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.328(6) . ?
C1 C2 1.384(8) . ?
C1 H1 0.9300 . ?
Cd1 O3 2.289(3) . ?
Cd1 O5 2.292(3) 1_545 ?
Cd1 O2 2.301(3) . ?
Cd1 O1 2.306(3) . ?
Cd1 N2 2.339(4) . ?
Cd1 N1 2.343(5) . ?
N1 C5 1.308(6) . ?
O1 H1B 0.99(2) . ?
O1 H1A 1.00(2) . ?
C2 C3 1.386(8) . ?
C2 H2 0.9300 . ?
N2 C12 1.317(7) . ?
N2 C16 1.327(7) . ?
O2 H2B 1.00(2) . ?
O2 H3A 0.995(14) . ?
C3 C4 1.388(8) . ?
C3 C6 1.502(7) . ?
O3 C23 1.261(5) . ?
C4 C5 1.392(8) . ?
C4 H4 0.9300 . ?
O4 C23 1.234(6) . ?
C5 H5 0.9300 . ?
O5 C26 1.268(5) . ?
O5 Cd1 2.292(3) 1_565 ?
C6 C11 1.314(11) . ?
C6 C7 1.342(11) . ?
O6 C26 1.227(6) . ?
C7 C8 1.410(13) . ?
C7 H7 0.9300 . ?
C8 C9 1.286(14) . ?
C8 H8 0.9300 . ?
C9 C10 1.316(14) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(13) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.379(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.385(10) . ?
C13 H13 0.9300 . ?
C14 C15 1.387(10) . ?
C14 C17 1.493(7) . ?
C15 C16 1.381(8) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.379(13) . ?
C17 C22 1.390(13) . ?
C18 C19 1.397(9) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(16) . ?
C19 H19 0.9300 . ?
C20 C21 1.378(17) . ?
C20 H20 0.9300 . ?
C21 C22 1.407(10) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.480(5) . ?
C24 C25 1.180(6) . ?
C25 C26 1.484(6) . ?

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 C1 C2 123.1(5) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
O3 Cd1 O5 178.18(11) . 1_545 ?
O3 Cd1 O2 90.83(12) . . ?
O5 Cd1 O2 88.54(11) 1_545 . ?
O3 Cd1 O1 88.32(11) . . ?
O5 Cd1 O1 92.67(12) 1_545 . ?
O2 Cd1 O1 167.32(14) . . ?
O3 Cd1 N2 91.87(14) . . ?
O5 Cd1 N2 89.76(14) 1_545 . ?
O2 Cd1 N2 84.15(14) . . ?
O1 Cd1 N2 83.23(14) . . ?
O3 Cd1 N1 89.00(13) . . ?
O5 Cd1 N1 89.38(13) 1_545 . ?
O2 Cd1 N1 96.41(13) . . ?
O1 Cd1 N1 96.23(13) . . ?
N2 Cd1 N1 178.96(14) . . ?
C5 N1 C1 119.0(5) . . ?
C5 N1 Cd1 121.3(3) . . ?
C1 N1 Cd1 119.7(3) . . ?
Cd1 O1 H1B 105(5) . . ?
Cd1 O1 H1A 128(5) . . ?
H1B O1 H1A 109(7) . . ?
C1 C2 C3 118.9(5) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C12 N2 C16 117.6(5) . . ?
C12 N2 Cd1 121.5(4) . . ?
C16 N2 Cd1 120.9(4) . . ?
Cd1 O2 H2B 124(5) . . ?
Cd1 O2 H3A 111(5) . . ?
H2B O2 H3A 106(7) . . ?
C2 C3 C4 117.0(5) . . ?
C2 C3 C6 119.9(5) . . ?
C4 C3 C6 123.1(5) . . ?
C23 O3 Cd1 127.3(3) . . ?
C3 C4 C5 120.3(5) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 121.7(5) . . ?
N1 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C26 O5 Cd1 125.6(3) . 1_565 ?
C11 C6 C7 115.3(7) . . ?
C11 C6 C3 122.3(7) . . ?
C7 C6 C3 122.4(7) . . ?
C6 C7 C8 121.4(9) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 122.3(10) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C8 C9 C10 116.1(8) . . ?
C8 C9 H9 121.9 . . ?
C10 C9 H9 121.9 . . ?
C9 C10 C11 123.0(10) . . ?
C9 C10 H10 118.5 . . ?
C11 C10 H10 118.5 . . ?
C6 C11 C10 121.8(10) . . ?
C6 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
N2 C12 C13 122.8(6) . . ?
N2 C12 H12 118.6 . . ?
C13 C12 H12 118.6 . . ?
C12 C13 C14 120.6(7) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C15 116.0(5) . . ?
C13 C14 C17 122.4(7) . . ?
C15 C14 C17 121.6(7) . . ?
C16 C15 C14 119.7(6) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
N2 C16 C15 123.3(6) . . ?
N2 C16 H16 118.4 . . ?
C15 C16 H16 118.4 . . ?
C18 C17 C22 119.1(7) . . ?
C18 C17 C14 120.8(8) . . ?
C22 C17 C14 120.1(8) . . ?
C17 C18 C19 121.0(10) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 119.9(10) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.2(7) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C22 120.2(10) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C17 C22 C21 119.7(10) . . ?
C17 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
O4 C23 O3 127.2(4) . . ?
O4 C23 C24 118.4(4) . . ?
O3 C23 C24 114.4(4) . . ?
C25 C24 C23 176.6(5) . . ?
C24 C25 C26 176.7(5) . . ?
O6 C26 O5 127.6(4) . . ?
O6 C26 C25 118.2(4) . . ?
O5 C26 C25 114.2(4) . . ?

_refine_diff_density_max         3.154
_refine_diff_density_min         -1.249
_refine_diff_density_rms         0.127

####################################################################### 
# 
# 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_232Zn_a
_database_code_depnum_ccdc_archive 'CCDC 1517764'
_audit_update_record             
;
2017-01-30 deposited with the CCDC.
2017-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H22 N2 O6 Zn'
_chemical_formula_weight         523.85

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                   9.8479(4)
_cell_length_b                   27.7163(13)
_cell_length_c                   9.3837(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.8410(10)
_cell_angle_gamma                90
_cell_volume                     2324.28(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      28.30

_exptl_crystal_description       rectengular
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    1.103
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17514
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.171
_diffrn_reflns_theta_max         28.308
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             2833
_reflns_number_gt                2611
_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-2014/7 (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)+(0.0412P)²+7.7437P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2833
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1180
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
C1 C 0.4289(3) 0.82610(10) 0.8193(4) 0.0411(6) Uani 1 1 d . . . . .
H1 H 0.3789 0.8093 0.8686 0.049 Uiso 1 1 calc R U . . .
N1 N 0.5000 0.80067(11) 0.7500 0.0333(6) Uani 1 2 d S T P . .
O1 O 0.4148(2) 0.71934(7) 0.5038(2) 0.0345(4) Uani 1 1 d . . . . .
H1A H 0.4830 0.7130 0.4785 0.052 Uiso 1 1 calc R U . . .
Zn1 Zn 0.5000 0.72379(2) 0.7500 0.02589(19) Uani 1 2 d S T P . .
C2 C 0.4257(3) 0.87579(11) 0.8216(4) 0.0434(7) Uani 1 1 d . . . . .
H2 H 0.3740 0.8916 0.8711 0.052 Uiso 1 1 calc R U . . .
N2 N 0.5000 0.64623(11) 0.7500 0.0326(6) Uani 1 2 d S T P . .
O2 O 0.72390(18) 0.72351(6) 0.7682(2) 0.0310(4) Uani 1 1 d . . . . .
C3 C 0.5000 0.90238(13) 0.7500 0.0329(7) Uani 1 2 d S T P . .
O3 O 0.6926(2) 0.69255(9) 0.5365(3) 0.0508(6) Uani 1 1 d . . . . .
C4 C 0.5000 0.95603(14) 0.7500 0.0363(7) Uani 1 2 d S T P . .
C5 C 0.5958(9) 0.98176(17) 0.7173(11) 0.155(4) Uani 1 1 d . . . . .
H5 H 0.6677 0.9659 0.6949 0.186 Uiso 1 1 calc R U . . .
C6 C 0.5930(10) 1.03182(17) 0.7153(13) 0.173(5) Uani 1 1 d . . . . .
H6 H 0.6610 1.0481 0.6878 0.207 Uiso 1 1 calc R U . . .
C7 C 0.5000 1.05709(17) 0.7500 0.0574(12) Uani 1 2 d S T P . .
H7 H 0.5000 1.0906 0.7500 0.069 Uiso 1 2 calc R U P . .
C8 C 0.3918(3) 0.62128(10) 0.6376(4) 0.0440(6) Uani 1 1 d . . . . .
H8 H 0.3156 0.6381 0.5585 0.053 Uiso 1 1 calc R U . . .
C9 C 0.3885(4) 0.57157(11) 0.6340(5) 0.0549(8) Uani 1 1 d . . . . .
H9 H 0.3110 0.5557 0.5532 0.066 Uiso 1 1 calc R U . . .
C10 C 0.5000 0.54494(15) 0.7500 0.0520(12) Uani 1 2 d S T P . .
C11 C 0.5000 0.49132(15) 0.7500 0.0672(17) Uani 1 2 d S T P . .
C12 C 0.4215(6) 0.46578(13) 0.6118(7) 0.0825(15) Uani 1 1 d . . . . .
H12 H 0.3688 0.4824 0.5187 0.099 Uiso 1 1 calc R U . . .
C13 C 0.4210(7) 0.41533(14) 0.6117(8) 0.099(2) Uani 1 1 d . . . . .
H13 H 0.3678 0.3985 0.5190 0.119 Uiso 1 1 calc R U . . .
C14 C 0.5000 0.39049(19) 0.7500 0.104(3) Uani 1 2 d S T P . .
H14 H 0.5000 0.3569 0.7500 0.125 Uiso 1 2 calc R U P . .
C15 C 0.7693(2) 0.70692(9) 0.6702(3) 0.0287(5) Uani 1 1 d . . . . .
C16 C 0.9339(3) 0.70546(9) 0.7267(3) 0.0317(5) Uani 1 1 d . . . . .
H1B H 0.358(5) 0.7388(15) 0.428(5) 0.064(12) 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
C1 N1 1.339(3) . ?
C1 C2 1.378(4) . ?
C1 H1 0.9300 . ?
N1 C1 1.339(3) 2_656 ?
N1 Zn1 2.131(3) . ?
O1 Zn1 2.1045(18) . ?
O1 H1A 0.8200 . ?
O1 H1B 0.88(4) . ?
Zn1 O1 2.1045(18) 2_656 ?
Zn1 O2 2.1389(16) 2_656 ?
Zn1 O2 2.1389(16) . ?
Zn1 N2 2.150(3) . ?
C2 C3 1.394(3) . ?
C2 H2 0.9300 . ?
N2 C8 1.335(3) . ?
N2 C8 1.335(3) 2_656 ?
O2 C15 1.266(3) . ?
C3 C2 1.394(3) 2_656 ?
C3 C4 1.487(5) . ?
O3 C15 1.228(3) . ?
C4 C5 1.317(5) 2_656 ?
C4 C5 1.317(5) . ?
C5 C6 1.388(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.298(6) . ?
C6 H6 0.9300 . ?
C7 C6 1.298(6) 2_656 ?
C7 H7 0.9300 . ?
C8 C9 1.378(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.390(4) . ?
C9 H9 0.9300 . ?
C10 C9 1.390(4) 2_656 ?
C10 C11 1.486(6) . ?
C11 C12 1.392(6) . ?
C11 C12 1.392(6) 2_656 ?
C12 C13 1.398(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(7) . ?
C13 H13 0.9300 . ?
C14 C13 1.384(7) 2_656 ?
C14 H14 0.9300 . ?
C15 C16 1.479(3) . ?
C16 C16 1.186(5) 2_756 ?

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 C1 C2 123.6(3) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C1 N1 C1 116.5(3) 2_656 . ?
C1 N1 Zn1 121.77(16) 2_656 . ?
C1 N1 Zn1 121.77(16) . . ?
Zn1 O1 H1A 109.5 . . ?
Zn1 O1 H1B 132(3) . . ?
H1A O1 H1B 102.7 . . ?
O1 Zn1 O1 173.28(11) 2_656 . ?
O1 Zn1 N1 93.36(6) 2_656 . ?
O1 Zn1 N1 93.36(6) . . ?
O1 Zn1 O2 90.54(7) 2_656 2_656 ?
O1 Zn1 O2 89.44(7) . 2_656 ?
N1 Zn1 O2 90.21(5) . 2_656 ?
O1 Zn1 O2 89.44(7) 2_656 . ?
O1 Zn1 O2 90.54(7) . . ?
N1 Zn1 O2 90.21(5) . . ?
O2 Zn1 O2 179.57(10) 2_656 . ?
O1 Zn1 N2 86.64(6) 2_656 . ?
O1 Zn1 N2 86.64(6) . . ?
N1 Zn1 N2 180.0 . . ?
O2 Zn1 N2 89.79(5) 2_656 . ?
O2 Zn1 N2 89.79(5) . . ?
C1 C2 C3 120.0(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C8 N2 C8 117.6(3) . 2_656 ?
C8 N2 Zn1 121.20(17) . . ?
C8 N2 Zn1 121.21(18) 2_656 . ?
C15 O2 Zn1 127.63(15) . . ?
C2 C3 C2 116.2(3) . 2_656 ?
C2 C3 C4 121.92(17) . . ?
C2 C3 C4 121.92(17) 2_656 . ?
C5 C4 C5 114.4(5) 2_656 . ?
C5 C4 C3 122.8(3) 2_656 . ?
C5 C4 C3 122.8(3) . . ?
C4 C5 C6 122.1(4) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C7 C6 C5 123.3(4) . . ?
C7 C6 H6 118.4 . . ?
C5 C6 H6 118.4 . . ?
C6 C7 C6 114.7(5) 2_656 . ?
C6 C7 H7 122.7 2_656 . ?
C6 C7 H7 122.7 . . ?
N2 C8 C9 122.7(3) . . ?
N2 C8 H8 118.7 . . ?
C9 C8 H8 118.7 . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C9 115.8(4) . 2_656 ?
C9 C10 C11 122.08(19) . . ?
C9 C10 C11 122.08(19) 2_656 . ?
C12 C11 C12 118.9(5) . 2_656 ?
C12 C11 C10 120.6(2) . . ?
C12 C11 C10 120.6(2) 2_656 . ?
C11 C12 C13 120.6(5) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 119.8(6) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C13 120.3(5) 2_656 . ?
C13 C14 H14 119.8 2_656 . ?
C13 C14 H14 119.8 . . ?
O3 C15 O2 127.3(2) . . ?
O3 C15 C16 118.0(2) . . ?
O2 C15 C16 114.7(2) . . ?
C16 C16 C15 178.34(18) 2_756 . ?

_refine_diff_density_max         1.047
_refine_diff_density_min         -1.036
_refine_diff_density_rms         0.072

