# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

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

data_qq
_database_code_depnum_ccdc_archive 'CCDC 1425153'
_audit_update_record             
;
2015-09-16 deposited with the CCDC.
2015-11-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        UTSA-67
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 N O5.50 Zn'
_chemical_formula_weight         419.68

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           hexagonal
_symmetry_space_group_name_H-M   P6522

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x-y, x, z+5/6'
'-y, x-y, z+2/3'
'-x, -y, z+1/2'
'-x+y, -x, z+1/3'
'y, -x+y, z+1/6'
'x-y, -y, -z'
'-x, -x+y, -z+1/3'
'y, x, -z+2/3'
'-y, -x, -z+1/6'
'-x+y, y, -z+1/2'
'x, x-y, -z+5/6'

_cell_length_a                   15.9684(5)
_cell_length_b                   15.9684(5)
_cell_length_c                   33.649(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     7430.6(9)
_cell_formula_units_Z            12
_cell_measurement_temperature    293(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          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2556
_exptl_absorpt_coefficient_mu    1.017
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15669
_diffrn_reflns_av_R_equivalents  0.1017
_diffrn_reflns_av_sigmaI/netI    0.0816
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         24.99
_reflns_number_total             4350
_reflns_number_gt                2642
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.2000P)²+0.4125P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.72(6)
_refine_ls_number_reflns         4350
_refine_ls_number_parameters     249
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.1616
_refine_ls_R_factor_gt           0.1139
_refine_ls_wR_factor_ref         0.3341
_refine_ls_wR_factor_gt          0.2978
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.066
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O5A O 0.432(4) 0.918(4) 0.9030(16) 0.30(3) Uiso 0.607(15) 1 d P A 2
C1 C 0.9143(7) 0.5819(8) 0.9423(4) 0.063(3) Uani 1 1 d . . .
C2 C 0.8708(5) 0.6405(4) 0.9532(2) 0.056(3) Uani 1 1 d G . .
C3 C 0.8317(5) 0.6304(5) 0.9910(2) 0.064(3) Uani 1 1 d G . .
H3 H 0.8360 0.5891 1.0093 0.077 Uiso 1 1 calc R . .
C4 C 0.7862(5) 0.6821(5) 1.00147(19) 0.071(3) Uani 1 1 d G . .
H4 H 0.7601 0.6753 1.0268 0.085 Uiso 1 1 calc R . .
C5 C 0.7798(6) 0.7439(5) 0.9741(2) 0.058(3) Uani 1 1 d G . .
C6 C 0.8188(7) 0.7540(6) 0.9363(2) 0.088(5) Uani 1 1 d G . .
H6 H 0.8145 0.7953 0.9180 0.106 Uiso 1 1 calc R . .
C7 C 0.8644(7) 0.7023(6) 0.92588(19) 0.084(4) Uani 1 1 d G . .
H7 H 0.8905 0.7091 0.9006 0.101 Uiso 1 1 calc R . .
C8 C 0.7243(8) 0.7962(7) 0.9835(4) 0.059(3) Uani 1 1 d . . .
C9 C 0.7753(7) 0.8960(7) 0.9881(3) 0.054(3) Uani 1 1 d . . .
H9 H 0.8423 0.9297 0.9856 0.065 Uiso 1 1 calc R . .
C10 C 0.7261(7) 0.9463(7) 0.9967(4) 0.060(3) Uani 1 1 d . . .
C11 C 0.6282(7) 0.8930(7) 1.0007(4) 0.068(3) Uani 1 1 d . . .
H11 H 0.5955 0.9258 1.0071 0.081 Uiso 1 1 calc R . .
C12 C 0.5735(8) 0.7932(9) 0.9960(5) 0.074(4) Uani 1 1 d . A .
C13 C 0.6253(8) 0.7421(7) 0.9869(4) 0.068(3) Uani 1 1 d . . .
C14 C 0.4683(7) 0.7392(6) 0.9980(4) 0.078(4) Uani 1 1 d D . .
C17 C 0.2660(7) 0.6250(8) 0.9991(4) 0.078(4) Uani 1 1 d D . .
C15 C 0.4129(12) 0.7479(16) 0.9678(6) 0.135(9) Uani 0.393(15) 1 d PDU A 1
H15 H 0.4433 0.7918 0.9472 0.162 Uiso 0.393(15) 1 calc PR A 1
C16 C 0.3119(12) 0.6911(16) 0.9684(6) 0.103(7) Uani 0.393(15) 1 d PDU A 1
H16 H 0.2754 0.6975 0.9483 0.123 Uiso 0.393(15) 1 calc PR A 1
C18 C 0.3204(11) 0.6159(17) 1.0295(6) 0.118(8) Uani 0.393(15) 1 d PDU A 1
H18 H 0.2897 0.5722 1.0501 0.141 Uiso 0.393(15) 1 calc PR A 1
C19 C 0.4215(11) 0.6730(16) 1.0289(5) 0.085(5) Uani 0.393(15) 1 d PDU A 1
H19 H 0.4577 0.6669 1.0492 0.102 Uiso 0.393(15) 1 calc PR A 1
C15A C 0.4184(11) 0.6914(13) 0.9629(4) 0.135(9) Uani 0.607(15) 1 d PDU A 2
H15A H 0.4522 0.6977 0.9395 0.162 Uiso 0.607(15) 1 calc PR A 2
C16A C 0.3173(11) 0.6344(13) 0.9637(4) 0.103(7) Uani 0.607(15) 1 d PDU A 2
H16A H 0.2839 0.6026 0.9409 0.123 Uiso 0.607(15) 1 calc PR A 2
C18A C 0.3165(11) 0.6724(13) 1.0333(4) 0.118(8) Uani 0.607(15) 1 d PDU A 2
H18A H 0.2833 0.6666 1.0567 0.141 Uiso 0.607(15) 1 calc PR A 2
C19A C 0.4167(10) 0.7283(12) 1.0323(4) 0.085(5) Uani 0.607(15) 1 d PDU A 2
H19A H 0.4498 0.7593 1.0553 0.102 Uiso 0.607(15) 1 calc PR A 2
C20 C 0.1584(10) 0.5582(9) 0.9997(6) 0.089(5) Uani 1 1 d . A .
N1 N 0.5719(7) 0.6404(6) 0.9836(3) 0.067(3) Uani 1 1 d . . .
H1A H 0.6061 0.6234 0.9675 0.081 Uiso 1 1 calc R . .
H1B H 0.5172 0.6258 0.9704 0.081 Uiso 1 1 calc R . .
O1 O 0.1129(7) 0.5366(10) 1.0325(4) 0.124(5) Uani 1 1 d . . .
O2 O 0.1201(6) 0.5297(7) 0.9673(3) 0.091(3) Uani 1 1 d . . .
O3 O 0.9162(6) 0.5249(6) 0.9674(3) 0.076(2) Uani 1 1 d . . .
O4 O 0.9461(7) 0.5929(6) 0.9073(3) 0.082(3) Uani 1 1 d . . .
Zn1 Zn 0.53190(9) 0.55007(9) 1.03182(5) 0.0714(5) Uani 1 1 d . . .
O5 O 0.391(3) 0.863(3) 0.8976(10) 0.116(11) Uiso 0.393(15) 1 d P A 1
O6 O 0.173(5) 0.786(6) 0.940(2) 0.37(4) Uiso 0.50 1 d P . .


_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 O3 1.254(14) . ?
C1 O4 1.258(14) . ?
C1 C2 1.464(12) . ?
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C5 C6 1.3900 . ?
C5 C8 1.523(10) . ?
C6 C7 1.3900 . ?
C8 C13 1.377(16) . ?
C8 C9 1.389(14) . ?
C9 C10 1.406(14) . ?
C10 C11 1.362(14) . ?
C10 C10 1.501(19) 7_677 ?
C11 C12 1.392(15) . ?
C12 C13 1.455(16) . ?
C12 C14 1.457(15) . ?
C13 N1 1.412(12) . ?
C14 C19A 1.377(9) . ?
C14 C19 1.404(9) . ?
C14 C15 1.401(9) . ?
C14 C15A 1.416(9) . ?
C17 C18A 1.392(9) . ?
C17 C18 1.397(9) . ?
C17 C16 1.395(9) . ?
C17 C16A 1.408(9) . ?
C17 C20 1.502(17) . ?
C15 C16 1.400(10) . ?
C18 C19 1.402(9) . ?
C15A C16A 1.402(9) . ?
C18A C19A 1.389(9) . ?
C20 O2 1.221(17) . ?
C20 O1 1.270(19) . ?
N1 Zn1 2.050(9) . ?
O2 Zn1 1.920(8) 7_567 ?
O3 Zn1 1.945(7) 7_667 ?
O4 Zn1 1.962(8) 2_654 ?
Zn1 O2 1.920(8) 7_667 ?
Zn1 O3 1.945(7) 7_567 ?
Zn1 O4 1.962(9) 6_565 ?

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
O3 C1 O4 125.2(11) . . ?
O3 C1 C2 119.2(11) . . ?
O4 C1 C2 115.6(11) . . ?
C3 C2 C7 120.0 . . ?
C3 C2 C1 118.9(7) . . ?
C7 C2 C1 121.0(7) . . ?
C2 C3 C4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 C8 118.4(6) . . ?
C4 C5 C8 121.5(6) . . ?
C5 C6 C7 120.0 . . ?
C6 C7 C2 120.0 . . ?
C13 C8 C9 122.7(9) . . ?
C13 C8 C5 118.3(8) . . ?
C9 C8 C5 119.0(9) . . ?
C8 C9 C10 120.3(9) . . ?
C11 C10 C9 117.2(9) . . ?
C11 C10 C10 121.4(6) . 7_677 ?
C9 C10 C10 121.3(6) . 7_677 ?
C10 C11 C12 124.9(9) . . ?
C11 C12 C13 117.3(10) . . ?
C11 C12 C14 123.4(11) . . ?
C13 C12 C14 119.2(10) . . ?
C8 C13 N1 123.9(10) . . ?
C8 C13 C12 117.5(9) . . ?
N1 C13 C12 118.5(11) . . ?
C19A C14 C19 39.1(10) . . ?
C19A C14 C15 104.6(10) . . ?
C19 C14 C15 119.2(9) . . ?
C19A C14 C15A 119.4(9) . . ?
C19 C14 C15A 105.6(10) . . ?
C15 C14 C15A 40.0(10) . . ?
C19A C14 C12 123.6(12) . . ?
C19 C14 C12 120.2(12) . . ?
C15 C14 C12 120.5(12) . . ?
C15A C14 C12 117.0(12) . . ?
C18A C17 C18 39.5(10) . . ?
C18A C17 C16 105.0(10) . . ?
C18 C17 C16 120.2(9) . . ?
C18A C17 C16A 119.4(9) . . ?
C18 C17 C16A 105.7(10) . . ?
C16 C17 C16A 40.3(10) . . ?
C18A C17 C20 121.3(13) . . ?
C18 C17 C20 117.7(12) . . ?
C16 C17 C20 122.0(13) . . ?
C16A C17 C20 119.1(13) . . ?
C16 C15 C14 120.4(12) . . ?
C17 C16 C15 120.0(11) . . ?
C17 C18 C19 119.8(12) . . ?
C14 C19 C18 120.4(11) . . ?
C16A C15A C14 119.2(11) . . ?
C15A C16A C17 120.4(11) . . ?
C17 C18A C19A 119.9(11) . . ?
C14 C19A C18A 121.7(11) . . ?
O2 C20 O1 124.1(13) . . ?
O2 C20 C17 115.7(16) . . ?
O1 C20 C17 120.2(15) . . ?
C13 N1 Zn1 122.9(8) . . ?
C20 O2 Zn1 115.4(10) . 7_567 ?
C1 O3 Zn1 132.2(8) . 7_667 ?
C1 O4 Zn1 143.5(8) . 2_654 ?
O2 Zn1 O3 112.7(4) 7_667 7_567 ?
O2 Zn1 O4 107.3(5) 7_667 6_565 ?
O3 Zn1 O4 116.2(4) 7_567 6_565 ?
O2 Zn1 N1 113.2(4) 7_667 . ?
O3 Zn1 N1 107.5(4) 7_567 . ?
O4 Zn1 N1 99.3(4) 6_565 . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.874
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.152
