# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1444088'
_audit_update_record             
;
2015-12-23 deposited with the CCDC.
2016-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H23 N3 O5 Zn'
_chemical_formula_weight         570.88

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n '

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

_cell_length_a                   9.861(2)
_cell_length_b                   28.306(6)
_cell_length_c                   10.024(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.863(4)
_cell_angle_gamma                90.00
_cell_volume                     2727.9(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      1.388
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_absorpt_coefficient_mu    0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7923
_exptl_absorpt_correction_T_max  0.8200
_exptl_absorpt_process_details   'SANABS; Bruker??2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19772
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4782
_reflns_number_gt                3675
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0709P)²+1.6572P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4782
_refine_ls_number_parameters     352
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1348
_refine_ls_wR_factor_gt          0.1277
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3630(4) 0.12666(14) 1.0149(4) 0.0481(9) Uani 1 1 d . . .
C2 C 0.3894(3) 0.15215(12) 0.8918(3) 0.0392(8) Uani 1 1 d . . .
C3 C 0.3981(4) 0.20123(12) 0.8917(4) 0.0417(8) Uani 1 1 d . . .
H3 H 0.3805 0.2182 0.9654 0.050 Uiso 1 1 calc R . .
C4 C 0.4323(4) 0.22479(12) 0.7842(4) 0.0411(8) Uani 1 1 d . . .
H4 H 0.4365 0.2576 0.7854 0.049 Uiso 1 1 calc R . .
C5 C 0.4608(3) 0.20010(11) 0.6732(3) 0.0367(8) Uani 1 1 d . . .
C6 C 0.4518(4) 0.15132(12) 0.6731(4) 0.0425(8) Uani 1 1 d . . .
H6 H 0.4711 0.1343 0.6002 0.051 Uiso 1 1 calc R . .
C7 C 0.4147(4) 0.12778(12) 0.7794(4) 0.0446(9) Uani 1 1 d . . .
H7 H 0.4064 0.0951 0.7762 0.054 Uiso 1 1 calc R . .
C8 C 1.1888(4) 0.13452(14) 0.3590(4) 0.0555(10) Uani 1 1 d . . .
H8 H 1.2795 0.1455 0.3876 0.067 Uiso 1 1 calc R . .
C9 C 1.0863(4) 0.15527(14) 0.4121(4) 0.0555(10) Uani 1 1 d . . .
H9 H 1.1091 0.1792 0.4767 0.067 Uiso 1 1 calc R . .
C10 C 0.9496(4) 0.14078(11) 0.3700(3) 0.0390(8) Uani 1 1 d . . .
C11 C 0.9242(4) 0.10449(13) 0.2752(4) 0.0489(9) Uani 1 1 d . . .
H11 H 0.8342 0.0932 0.2439 0.059 Uiso 1 1 calc R . .
C12 C 1.0324(4) 0.08518(13) 0.2275(4) 0.0474(9) Uani 1 1 d . . .
H12 H 1.0127 0.0610 0.1634 0.057 Uiso 1 1 calc R . .
C13 C 0.8349(4) 0.16312(11) 0.4212(3) 0.0394(8) Uani 1 1 d . . .
C14 C 0.8535(4) 0.17728(13) 0.5571(4) 0.0455(9) Uani 1 1 d . . .
H14 H 0.9393 0.1730 0.6171 0.055 Uiso 1 1 calc R . .
C15 C 0.7451(4) 0.19758(13) 0.6033(4) 0.0479(9) Uani 1 1 d . . .
H15 H 0.7585 0.2070 0.6942 0.057 Uiso 1 1 calc R . .
C16 C 0.6168(4) 0.20400(11) 0.5155(3) 0.0391(8) Uani 1 1 d . . .
C17 C 0.5990(4) 0.19112(12) 0.3803(4) 0.0443(9) Uani 1 1 d . . .
H17 H 0.5142 0.1964 0.3196 0.053 Uiso 1 1 calc R . .
C18 C 0.7063(4) 0.17044(13) 0.3348(4) 0.0442(8) Uani 1 1 d . . .
H18 H 0.6922 0.1611 0.2438 0.053 Uiso 1 1 calc R . .
C19 C 0.1698(4) 0.47589(12) 0.4143(4) 0.0469(9) Uani 1 1 d . . .
H19 H 0.1078 0.4907 0.4582 0.056 Uiso 1 1 calc R . .
C20 C 0.2070(4) 0.42995(12) 0.4487(4) 0.0466(9) Uani 1 1 d . . .
H20 H 0.1691 0.4142 0.5133 0.056 Uiso 1 1 calc R . .
C21 C 0.3019(4) 0.40697(11) 0.3863(3) 0.0384(8) Uani 1 1 d . . .
C22 C 0.3481(5) 0.43225(12) 0.2868(4) 0.0518(10) Uani 1 1 d . . .
H22 H 0.4089 0.4182 0.2397 0.062 Uiso 1 1 calc R . .
C23 C 0.3048(5) 0.47762(13) 0.2573(4) 0.0536(10) Uani 1 1 d . . .
H23 H 0.3371 0.4936 0.1895 0.064 Uiso 1 1 calc R . .
C24 C 0.3517(4) 0.35878(11) 0.4276(3) 0.0368(8) Uani 1 1 d . . .
C25 C 0.2668(4) 0.32591(11) 0.4728(3) 0.0384(8) Uani 1 1 d . . .
H25 H 0.1756 0.3341 0.4737 0.046 Uiso 1 1 calc R . .
C26 C 0.3150(4) 0.28156(12) 0.5162(3) 0.0399(8) Uani 1 1 d . . .
H26 H 0.2557 0.2601 0.5446 0.048 Uiso 1 1 calc R . .
C27 C 0.4517(4) 0.26842(11) 0.5180(3) 0.0376(8) Uani 1 1 d . . .
C28 C 0.5369(4) 0.30103(12) 0.4718(4) 0.0471(9) Uani 1 1 d . . .
H28 H 0.6283 0.2930 0.4716 0.056 Uiso 1 1 calc R . .
C29 C 0.4868(4) 0.34508(12) 0.4265(4) 0.0451(9) Uani 1 1 d . . .
H29 H 0.5447 0.3661 0.3944 0.054 Uiso 1 1 calc R . .
C30 C 0.5831(5) 0.05800(19) 1.3626(6) 0.0733(13) Uani 1 1 d . . .
H30 H 0.6572 0.0554 1.4380 0.088 Uiso 1 1 calc R . .
N1 N 1.1642(3) 0.09936(10) 0.2685(3) 0.0421(7) Uani 1 1 d . . .
N2 N 0.2182(3) 0.50028(10) 0.3210(3) 0.0426(7) Uani 1 1 d . . .
N3 N 0.5037(3) 0.22418(10) 0.5653(3) 0.0447(7) Uani 1 1 d . . .
O1 O 0.3311(4) 0.08348(10) 1.0043(3) 0.0684(8) Uani 1 1 d . . .
O2 O 0.3744(3) 0.14831(13) 1.1242(3) 0.0741(9) Uani 1 1 d . . .
O3 O 0.6021(4) 0.04515(15) 1.2523(4) 0.0939(11) Uani 1 1 d . . .
O4 O 0.4705(3) 0.07455(10) 1.3823(3) 0.0643(8) Uani 1 1 d . . .
O5 O 0.1818(6) 0.0204(2) 0.7727(6) 0.157(2) Uani 1 1 d U . .
H5D H 0.2231 0.0383 0.8372 0.188 Uiso 1 1 d R . .
H5B H 0.2161 -0.0073 0.7847 0.235 Uiso 1 1 d R . .
Zn1 Zn 0.33287(4) 0.071008(13) 1.20600(4) 0.03995(16) 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
C1 O2 1.238(5) . ?
C1 O1 1.260(5) . ?
C1 C2 1.501(5) . ?
C2 C7 1.390(5) . ?
C2 C3 1.392(5) . ?
C3 C4 1.372(5) . ?
C4 C5 1.394(5) . ?
C5 C6 1.384(5) . ?
C5 N3 1.420(4) . ?
C6 C7 1.374(5) . ?
C8 N1 1.332(5) . ?
C8 C9 1.375(5) . ?
C9 C10 1.382(5) . ?
C10 C11 1.383(5) . ?
C10 C13 1.483(5) . ?
C11 C12 1.376(5) . ?
C12 N1 1.334(5) . ?
C13 C18 1.382(5) . ?
C13 C14 1.393(5) . ?
C14 C15 1.381(5) . ?
C15 C16 1.383(5) . ?
C16 C17 1.377(5) . ?
C16 N3 1.438(4) . ?
C17 C18 1.373(5) . ?
C19 N2 1.332(4) . ?
C19 C20 1.374(5) . ?
C20 C21 1.396(5) . ?
C21 C22 1.385(5) . ?
C21 C24 1.478(5) . ?
C22 C23 1.365(5) . ?
C23 N2 1.338(5) . ?
C24 C29 1.390(5) . ?
C24 C25 1.393(5) . ?
C25 C26 1.378(5) . ?
C26 C27 1.394(5) . ?
C27 N3 1.396(4) . ?
C27 C28 1.395(5) . ?
C28 C29 1.380(5) . ?
C30 O3 1.217(6) . ?
C30 O4 1.261(6) . ?
N1 Zn1 2.066(3) 1_654 ?
N2 Zn1 2.068(3) 2_556 ?
O1 Zn1 2.049(3) . ?
O2 Zn1 2.404(3) . ?
O4 Zn1 1.976(3) . ?
Zn1 N1 2.066(3) 1_456 ?
Zn1 N2 2.068(3) 2_546 ?

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 C1 O1 121.8(4) . . ?
O2 C1 C2 119.4(4) . . ?
O1 C1 C2 118.8(4) . . ?
C7 C2 C3 118.2(3) . . ?
C7 C2 C1 121.5(3) . . ?
C3 C2 C1 120.1(3) . . ?
C4 C3 C2 120.8(3) . . ?
C3 C4 C5 120.8(3) . . ?
C6 C5 C4 118.5(3) . . ?
C6 C5 N3 120.5(3) . . ?
C4 C5 N3 121.0(3) . . ?
C7 C6 C5 120.7(3) . . ?
C6 C7 C2 121.0(3) . . ?
N1 C8 C9 123.0(4) . . ?
C8 C9 C10 120.4(4) . . ?
C9 C10 C11 116.4(3) . . ?
C9 C10 C13 122.3(3) . . ?
C11 C10 C13 121.3(3) . . ?
C12 C11 C10 119.8(4) . . ?
N1 C12 C11 123.4(3) . . ?
C18 C13 C14 118.2(3) . . ?
C18 C13 C10 120.7(3) . . ?
C14 C13 C10 121.1(3) . . ?
C15 C14 C13 120.3(3) . . ?
C14 C15 C16 120.5(3) . . ?
C17 C16 C15 119.3(3) . . ?
C17 C16 N3 120.6(3) . . ?
C15 C16 N3 120.1(3) . . ?
C18 C17 C16 120.0(3) . . ?
C17 C18 C13 121.6(3) . . ?
N2 C19 C20 123.3(3) . . ?
C19 C20 C21 119.7(3) . . ?
C22 C21 C20 116.3(3) . . ?
C22 C21 C24 122.5(3) . . ?
C20 C21 C24 121.2(3) . . ?
C23 C22 C21 120.3(3) . . ?
N2 C23 C22 123.4(3) . . ?
C29 C24 C25 117.6(3) . . ?
C29 C24 C21 121.0(3) . . ?
C25 C24 C21 121.4(3) . . ?
C26 C25 C24 121.4(3) . . ?
C25 C26 C27 120.8(3) . . ?
N3 C27 C28 120.2(3) . . ?
N3 C27 C26 121.7(3) . . ?
C28 C27 C26 118.1(3) . . ?
C29 C28 C27 120.6(3) . . ?
C28 C29 C24 121.5(3) . . ?
O3 C30 O4 124.9(5) . . ?
C8 N1 C12 116.9(3) . . ?
C8 N1 Zn1 117.3(3) . 1_654 ?
C12 N1 Zn1 125.8(2) . 1_654 ?
C19 N2 C23 116.9(3) . . ?
C19 N2 Zn1 118.6(2) . 2_556 ?
C23 N2 Zn1 124.3(2) . 2_556 ?
C27 N3 C5 122.7(3) . . ?
C27 N3 C16 119.5(3) . . ?
C5 N3 C16 117.4(3) . . ?
C1 O1 Zn1 97.9(3) . . ?
C1 O2 Zn1 82.1(2) . . ?
C30 O4 Zn1 107.1(3) . . ?
O4 Zn1 O1 136.63(14) . . ?
O4 Zn1 N1 98.52(12) . 1_456 ?
O1 Zn1 N1 113.69(12) . 1_456 ?
O4 Zn1 N2 105.37(12) . 2_546 ?
O1 Zn1 N2 95.12(12) . 2_546 ?
N1 Zn1 N2 103.11(12) 1_456 2_546 ?
O4 Zn1 O2 97.11(11) . . ?
O1 Zn1 O2 58.06(11) . . ?
N1 Zn1 O2 87.70(12) 1_456 . ?
N2 Zn1 O2 153.10(11) 2_546 . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.062
