# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_mm
_database_code_depnum_ccdc_archive 'CCDC 940997'
_audit_update_record             
;
2013-05-24 deposited with the CCDC.
2015-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H15 N3 O6 Zn'
_chemical_formula_weight         422.71

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           Rhombohedral
_symmetry_space_group_name_H-M   R-3

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

_cell_length_a                   29.935(4)
_cell_length_b                   29.935(4)
_cell_length_c                   11.194(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     8687(2)
_cell_formula_units_Z            18
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7976
_cell_measurement_theta_min      1.9814
_cell_measurement_theta_max      27.8864

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3887
_exptl_absorpt_coefficient_mu    1.309
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7094
_exptl_absorpt_correction_T_max  1.0000
_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  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27432
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_sigmaI/netI    0.0541
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         27.83
_reflns_number_total             4570
_reflns_number_gt                3979
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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)+(0.1158P)²+18.3144P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4570
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0790
_refine_ls_R_factor_gt           0.0700
_refine_ls_wR_factor_ref         0.1981
_refine_ls_wR_factor_gt          0.1907
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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
Zn1 Zn -0.030837(16) 0.243511(17) 0.85398(3) 0.02683(18) Uani 1 1 d . . .
O1 O 0.03476(10) 0.24262(12) 0.8552(2) 0.0327(6) Uani 1 1 d . . .
O2 O 0.03696(11) 0.27680(11) 0.6781(2) 0.0332(6) Uani 1 1 d . . .
O3 O 0.19967(11) 0.26943(11) 1.0121(2) 0.0307(6) Uani 1 1 d . . .
O4 O 0.26252(10) 0.27746(10) 0.8899(2) 0.0286(6) Uani 1 1 d . . .
O5 O -0.01976(12) 0.31488(11) 0.8534(2) 0.0362(7) Uani 1 1 d . . .
H5A H 0.0124 0.3366 0.8538 0.043 Uiso 1 1 d R . .
H5B H -0.0337 0.3194 0.9153 0.043 Uiso 1 1 d R . .
N1 N 0.19837(13) 0.29806(13) 0.4770(2) 0.0278(7) Uani 1 1 d . . .
N2 N 0.23471(14) 0.34491(13) 0.3162(3) 0.0314(7) Uani 1 1 d . . .
N3 N 0.21375(14) 0.29265(13) 0.2892(3) 0.0320(7) Uani 1 1 d . . .
C1 C 0.05667(15) 0.26203(15) 0.7545(3) 0.0272(7) Uani 1 1 d . . .
C2 C 0.10859(14) 0.26769(14) 0.7324(3) 0.0256(7) Uani 1 1 d . . .
C3 C 0.12848(14) 0.27818(15) 0.6162(3) 0.0270(7) Uani 1 1 d . . .
H3 H 0.1091 0.2799 0.5533 0.032 Uiso 1 1 calc R . .
C4 C 0.17746(15) 0.28594(15) 0.5968(3) 0.0279(8) Uani 1 1 d . . .
C5 C 0.20825(15) 0.28475(15) 0.6899(3) 0.0287(8) Uani 1 1 d . . .
H5 H 0.2414 0.2907 0.6751 0.034 Uiso 1 1 calc R . .
C6 C 0.18770(14) 0.27434(14) 0.8054(3) 0.0252(7) Uani 1 1 d . . .
C7 C 0.13780(14) 0.26515(14) 0.8261(3) 0.0248(7) Uani 1 1 d . . .
H7 H 0.1240 0.2573 0.9027 0.030 Uiso 1 1 calc R . .
C8 C 0.23856(17) 0.39412(17) 0.5003(3) 0.0355(9) Uani 1 1 d . . .
H8A H 0.2077 0.3926 0.5299 0.053 Uiso 1 1 calc R . .
H8B H 0.2569 0.4240 0.4506 0.053 Uiso 1 1 calc R . .
H8C H 0.2600 0.3962 0.5663 0.053 Uiso 1 1 calc R . .
C9 C 0.22466(15) 0.34703(15) 0.4294(3) 0.0282(8) Uani 1 1 d . . .
C10 C 0.19192(16) 0.26515(16) 0.3858(3) 0.0301(8) Uani 1 1 d . . .
C11 C 0.16484(18) 0.20827(17) 0.3917(3) 0.0363(9) Uani 1 1 d . . .
C12 C 0.13456(19) 0.17966(19) 0.2939(4) 0.0451(11) Uani 1 1 d . . .
H12 H 0.1310 0.1968 0.2284 0.054 Uiso 1 1 calc R . .
C13 C 0.1098(2) 0.1261(2) 0.2941(5) 0.0593(14) Uani 1 1 d . . .
H13 H 0.0900 0.1074 0.2290 0.071 Uiso 1 1 calc R . .
C14 C 0.1150(2) 0.1007(2) 0.3919(5) 0.0612(15) Uani 1 1 d . . .
H14 H 0.0979 0.0648 0.3932 0.073 Uiso 1 1 calc R . .
C15 C 0.1457(2) 0.1285(2) 0.4880(5) 0.0590(14) Uani 1 1 d . . .
H15 H 0.1496 0.1112 0.5525 0.071 Uiso 1 1 calc R . .
C16 C 0.1706(2) 0.1821(2) 0.4885(4) 0.0483(12) Uani 1 1 d . . .
H16 H 0.1910 0.2005 0.5532 0.058 Uiso 1 1 calc R . .
C17 C 0.21990(14) 0.27380(14) 0.9085(3) 0.0255(7) Uani 1 1 d . . .
O6 O 0.0000 0.0000 0.848(3) 0.40(3) Uani 0.75 3 d SP . .
H6 H 0.0213 0.0274 0.8758 0.479 Uiso 0.50 1 d PR . .
O7 O 0.1616(4) 0.1196(5) 1.0003(7) 0.139(6) Uani 0.50 1 d P . .
H7A H 0.1539 0.1416 0.9744 0.167 Uiso 0.50 1 d PR . .
H7B H 0.1360 0.0894 0.9914 0.167 Uiso 0.50 1 d PR . .
O9 O 0.0544(9) 0.0891(9) 0.978(2) 0.107(8) Uani 0.25 1 d P . .
H9 H 0.0726 0.0989 0.9197 0.128 Uiso 0.50 1 d PR . .


_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 O3 1.949(2) 12_557 ?
Zn1 O1 1.977(3) . ?
Zn1 O5 1.991(3) . ?
Zn1 N3 2.037(3) 12_556 ?
O1 C1 1.287(4) . ?
O2 C1 1.240(4) . ?
O3 C17 1.284(4) . ?
O3 Zn1 1.949(2) 11_557 ?
O4 C17 1.242(4) . ?
O5 H5A 0.8513 . ?
O5 H5B 0.8534 . ?
N1 C10 1.364(5) . ?
N1 C9 1.378(5) . ?
N1 C4 1.447(4) . ?
N2 C9 1.312(4) . ?
N2 N3 1.397(5) . ?
N3 C10 1.318(5) . ?
N3 Zn1 2.037(3) 11_556 ?
C1 C2 1.498(5) . ?
C2 C7 1.391(5) . ?
C2 C3 1.399(5) . ?
C3 C4 1.382(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.403(5) . ?
C5 C6 1.398(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.396(5) . ?
C6 C17 1.509(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.484(5) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C10 C11 1.477(6) . ?
C11 C16 1.397(6) . ?
C11 C12 1.406(6) . ?
C12 C13 1.390(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.385(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.390(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.390(7) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
O6 H6 0.8071 . ?
O7 H7A 0.8491 . ?
O7 H7B 0.8501 . ?
O9 H9 0.8038 . ?

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 Zn1 O1 104.41(11) 12_557 . ?
O3 Zn1 O5 116.59(11) 12_557 . ?
O1 Zn1 O5 112.38(12) . . ?
O3 Zn1 N3 104.89(12) 12_557 12_556 ?
O1 Zn1 N3 119.26(12) . 12_556 ?
O5 Zn1 N3 99.73(13) . 12_556 ?
C1 O1 Zn1 105.8(2) . . ?
C17 O3 Zn1 114.9(2) . 11_557 ?
Zn1 O5 H5A 109.6 . . ?
Zn1 O5 H5B 109.5 . . ?
H5A O5 H5B 109.4 . . ?
C10 N1 C9 106.2(3) . . ?
C10 N1 C4 128.7(3) . . ?
C9 N1 C4 124.7(3) . . ?
C9 N2 N3 106.1(3) . . ?
C10 N3 N2 109.1(3) . . ?
C10 N3 Zn1 128.6(3) . 11_556 ?
N2 N3 Zn1 117.4(2) . 11_556 ?
O2 C1 O1 122.7(3) . . ?
O2 C1 C2 119.8(3) . . ?
O1 C1 C2 117.5(3) . . ?
C7 C2 C3 120.3(3) . . ?
C7 C2 C1 121.0(3) . . ?
C3 C2 C1 118.7(3) . . ?
C4 C3 C2 118.7(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 122.3(3) . . ?
C3 C4 N1 118.5(3) . . ?
C5 C4 N1 119.2(3) . . ?
C6 C5 C4 118.1(3) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 C17 119.8(3) . . ?
C5 C6 C17 119.8(3) . . ?
C2 C7 C6 120.2(3) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 N1 110.2(3) . . ?
N2 C9 C8 126.9(4) . . ?
N1 C9 C8 122.9(3) . . ?
N3 C10 N1 108.4(3) . . ?
N3 C10 C11 124.9(3) . . ?
N1 C10 C11 126.7(3) . . ?
C16 C11 C12 119.0(4) . . ?
C16 C11 C10 122.1(4) . . ?
C12 C11 C10 118.8(4) . . ?
C13 C12 C11 120.7(5) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 119.6(5) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 120.3(5) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 120.5(5) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 119.9(5) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
O4 C17 O3 124.8(3) . . ?
O4 C17 C6 120.3(3) . . ?
O3 C17 C6 114.9(3) . . ?
H7A O7 H7B 109.6 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.83
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.317
_refine_diff_density_min         -1.274
_refine_diff_density_rms         0.129
