# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_C:
_database_code_depnum_ccdc_archive 'CCDC 1836214'
_audit_update_record             
;
2018-05-17 deposited with the CCDC.
2018-10-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H0 N7 O1.17 S2 Zn'
_chemical_formula_weight         330.30

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'
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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-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                   23.390(7)
_cell_length_b                   23.390(7)
_cell_length_c                   13.909(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     6590(4)
_cell_formula_units_Z            18
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2417
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      25.32

_exptl_crystal_description       Prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_F_000             2922
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.961
_shelx_estimated_absorpt_T_min   0.757
_shelx_estimated_absorpt_T_max   0.828
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_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            7174
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.741
_diffrn_reflns_theta_max         25.480
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2711
_reflns_number_gt                2092
_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)+(0.1004P)²+39.1955P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2711
_refine_ls_number_parameters     193
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1848
_refine_ls_wR_factor_gt          0.1686
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.074
_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 0.22977(3) 0.97111(3) 0.06902(4) 0.0369(3) Uani 1 1 d . . . . .
N1 N 0.3289(2) 1.0447(2) 0.3237(3) 0.0445(11) Uani 1 1 d . . . . .
N3 N 0.2620(2) 0.9953(2) 0.2024(3) 0.0433(11) Uani 1 1 d . . . . .
N6 N 0.1381(2) 0.8957(2) 0.0605(3) 0.0468(12) Uani 1 1 d . . . . .
C4 C 0.1067(3) 0.8594(3) -0.0159(4) 0.0473(11) Uani 1 1 d . U . . .
N4 N 0.0451(2) 0.8162(2) 0.0004(3) 0.0485(10) Uani 1 1 d . U . . .
C2 C 0.3228(3) 1.0366(3) 0.2300(4) 0.0548(16) Uani 1 1 d . . . . .
N2B N 0.2666(13) 1.0189(12) 0.3561(15) 0.058(5) Uani 0.5 1 d . . P A -1
C1A C 0.2345(8) 0.9647(7) 0.2881(12) 0.052(4) Uani 0.5 1 d . U P A 1
N2A N 0.2722(11) 0.9952(11) 0.3641(16) 0.064(6) Uani 0.5 1 d . . P A 1
C1B C 0.2279(6) 0.9902(8) 0.2844(8) 0.045(3) Uani 0.5 1 d . . P A -1
N7 N 0.2024(6) 1.1374(6) 0.3657(9) 0.141(4) Uiso 1 1 d . . . . .
C5 C 0.2122(8) 1.1262(8) 0.2729(12) 0.151(5) Uiso 1 1 d . . . . .
C7 C 0.1340(12) 1.0896(12) 0.3998(17) 0.246(10) Uiso 1 1 d . . . . .
O1 O 0.2710(5) 1.1613(5) 0.2373(7) 0.156(3) Uiso 1 1 d . . . . .
C6 C 0.2506(13) 1.1823(15) 0.429(2) 0.276(12) Uiso 1 1 d . . . . .
O2 O 0.0000 1.0000 0.0000 0.30(2) Uiso 1 6 d S . P . .
C3A C 0.0854(9) 0.8848(9) 0.1134(11) 0.058(4) Uani 0.5 1 d . . P A 1
C3B C 0.0961(9) 0.8578(10) 0.1349(11) 0.064(5) Uani 0.5 1 d . . P A -1
S1A S 0.1537(3) 0.8968(3) 0.3030(3) 0.123(3) Uani 0.5 1 d . . P A 1
S2A S 0.09353(19) 0.9242(3) 0.2240(4) 0.123(3) Uani 0.5 1 d . . P A 1
S3B S 0.1126(3) 0.8629(3) 0.2589(3) 0.119(2) Uani 0.5 1 d . . P A -1
S2B S 0.1443(2) 0.9550(4) 0.2903(4) 0.116(2) Uani 0.5 1 d . . P A -1
N5B N 0.0381(9) 0.8109(9) 0.1025(10) 0.070(5) Uani 0.5 1 d . . P A -1
N5A N 0.0286(9) 0.8375(9) 0.0819(12) 0.065(4) Uani 0.5 1 d . . P A 1


_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 N3 1.975(4) . ?
Zn1 N6 1.985(5) . ?
Zn1 N4 1.990(5) 12_665 ?
Zn1 N1 1.992(4) 8_664 ?
N1 C2 1.314(7) . ?
N1 N2B 1.35(3) . ?
N1 N2A 1.37(2) . ?
N1 Zn1 1.992(4) 6_465 ?
N3 C2 1.314(7) . ?
N3 C1B 1.364(11) . ?
N3 C1A 1.374(16) . ?
N6 C4 1.328(7) . ?
N6 C3A 1.347(17) . ?
N6 C3B 1.397(17) . ?
C4 N4 1.301(7) . ?
C4 C3A 2.033(16) . ?
N4 N5A 1.369(17) . ?
N4 N5B 1.428(15) . ?
N4 Zn1 1.990(5) 11_455 ?
N2B N2A 0.64(2) . ?
N2B C1B 1.29(3) . ?
N2B C1A 1.45(3) . ?
C1A C1B 0.689(16) . ?
C1A N2A 1.33(3) . ?
C1A S1A 1.772(16) . ?
C1A S2B 2.006(16) . ?
N2A C1B 1.48(2) . ?
C1B S2B 1.701(12) . ?
C1B S1A 2.014(15) . ?
N7 C5 1.360(17) . ?
N7 C6 1.40(3) . ?
N7 C7 1.50(2) . ?
C5 O1 1.296(16) . ?
C3A C3B 0.84(2) . ?
C3A N5A 1.31(2) . ?
C3A N5B 1.52(3) . ?
C3A S2A 1.754(15) . ?
C3A S3B 2.255(18) . ?
C3B N5B 1.33(2) . ?
C3B N5A 1.59(2) . ?
C3B S3B 1.757(16) . ?
C3B S2A 2.01(2) . ?
S1A S3B 1.080(6) . ?
S1A S2B 1.493(10) . ?
S1A S2A 2.121(11) . ?
S2A S2B 1.387(6) . ?
S2A S3B 1.769(10) . ?
S3B S2B 1.945(11) . ?
N5B N5A 0.809(19) . ?

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
N3 Zn1 N6 113.52(19) . . ?
N3 Zn1 N4 112.00(19) . 12_665 ?
N6 Zn1 N4 105.6(2) . 12_665 ?
N3 Zn1 N1 111.90(19) . 8_664 ?
N6 Zn1 N1 108.88(19) . 8_664 ?
N4 Zn1 N1 104.4(2) 12_665 8_664 ?
C2 N1 N2B 104.6(11) . . ?
C2 N1 N2A 107.2(11) . . ?
N2B N1 N2A 27.3(10) . . ?
C2 N1 Zn1 129.8(4) . 6_465 ?
N2B N1 Zn1 123.3(11) . 6_465 ?
N2A N1 Zn1 122.0(10) . 6_465 ?
C2 N3 C1B 101.0(6) . . ?
C2 N3 C1A 100.4(8) . . ?
C1B N3 C1A 29.1(7) . . ?
C2 N3 Zn1 127.1(4) . . ?
C1B N3 Zn1 129.6(6) . . ?
C1A N3 Zn1 130.8(7) . . ?
C4 N6 C3A 98.9(8) . . ?
C4 N6 C3B 101.5(8) . . ?
C3A N6 C3B 35.8(9) . . ?
C4 N6 Zn1 128.5(4) . . ?
C3A N6 Zn1 127.9(8) . . ?
C3B N6 Zn1 128.6(7) . . ?
N4 C4 N6 113.7(5) . . ?
N4 C4 C3A 74.6(6) . . ?
N6 C4 C3A 40.9(5) . . ?
C4 N4 N5A 105.3(9) . . ?
C4 N4 N5B 105.9(8) . . ?
N5A N4 N5B 33.5(8) . . ?
C4 N4 Zn1 137.5(4) . 11_455 ?
N5A N4 Zn1 116.3(8) . 11_455 ?
N5B N4 Zn1 113.3(8) . 11_455 ?
N1 C2 N3 113.3(5) . . ?
N2A N2B C1B 94(5) . . ?
N2A N2B N1 78(4) . . ?
C1B N2B N1 107.3(16) . . ?
N2A N2B C1A 66(4) . . ?
C1B N2B C1A 28.3(9) . . ?
N1 N2B C1A 98.3(15) . . ?
C1B C1A N2A 88(2) . . ?
C1B C1A N3 74.6(18) . . ?
N2A C1A N3 113.4(14) . . ?
C1B C1A N2B 62.3(18) . . ?
N2A C1A N2B 26.2(10) . . ?
N3 C1A N2B 101.9(13) . . ?
C1B C1A S1A 100(2) . . ?
N2A C1A S1A 120.8(14) . . ?
N3 C1A S1A 125.5(11) . . ?
N2B C1A S1A 124.1(14) . . ?
C1B C1A S2B 54.5(18) . . ?
N2A C1A S2B 115.2(14) . . ?
N3 C1A S2B 105.3(9) . . ?
N2B C1A S2B 98.3(12) . . ?
S1A C1A S2B 46.0(5) . . ?
N2B N2A C1A 88(4) . . ?
N2B N2A N1 74(4) . . ?
C1A N2A N1 103.2(16) . . ?
N2B N2A C1B 60(4) . . ?
C1A N2A C1B 27.7(8) . . ?
N1 N2A C1B 95.9(13) . . ?
C1A C1B N2B 89(2) . . ?
C1A C1B N3 76.3(17) . . ?
N2B C1B N3 111.9(14) . . ?
C1A C1B N2A 64(2) . . ?
N2B C1B N2A 25.6(13) . . ?
N3 C1B N2A 105.2(12) . . ?
C1A C1B S2B 106(2) . . ?
N2B C1B S2B 123.6(13) . . ?
N3 C1B S2B 124.3(8) . . ?
N2A C1B S2B 126.3(12) . . ?
C1A C1B S1A 59.9(19) . . ?
N2B C1B S1A 117.8(13) . . ?
N3 C1B S1A 110.6(8) . . ?
N2A C1B S1A 100.3(12) . . ?
S2B C1B S1A 46.4(5) . . ?
C5 N7 C6 126.1(17) . . ?
C5 N7 C7 112.2(15) . . ?
C6 N7 C7 121.3(18) . . ?
O1 C5 N7 118.0(14) . . ?
C3B C3A N5A 92(2) . . ?
C3B C3A N6 75(2) . . ?
N5A C3A N6 115.0(13) . . ?
C3B C3A N5B 60(2) . . ?
N5A C3A N5B 32.1(9) . . ?
N6 C3A N5B 103.7(13) . . ?
C3B C3A S2A 95(2) . . ?
N5A C3A S2A 122.4(13) . . ?
N6 C3A S2A 122.1(11) . . ?
N5B C3A S2A 120.6(12) . . ?
C3B C3A C4 83.4(19) . . ?
N5A C3A C4 75.5(10) . . ?
N6 C3A C4 40.2(5) . . ?
N5B C3A C4 74.1(9) . . ?
S2A C3A C4 162.1(11) . . ?
C3B C3A S3B 44.6(18) . . ?
N5A C3A S3B 113.0(14) . . ?
N6 C3A S3B 101.4(10) . . ?
N5B C3A S3B 87.7(11) . . ?
S2A C3A S3B 50.5(5) . . ?
C4 C3A S3B 126.1(9) . . ?
C3A C3B N5B 86(2) . . ?
C3A C3B N6 68.9(18) . . ?
N5B C3B N6 112.1(13) . . ?
C3A C3B N5A 55.5(19) . . ?
N5B C3B N5A 30.6(10) . . ?
N6 C3B N5A 97.1(12) . . ?
C3A C3B S3B 116(2) . . ?
N5B C3B S3B 119.2(12) . . ?
N6 C3B S3B 128.6(12) . . ?
N5A C3B S3B 128.9(13) . . ?
C3A C3B S2A 60.2(19) . . ?
N5B C3B S2A 115.6(16) . . ?
N6 C3B S2A 104.4(12) . . ?
N5A C3B S2A 96.1(13) . . ?
S3B C3B S2A 55.5(6) . . ?
S3B S1A S2B 96.9(8) . . ?
S3B S1A C1A 138.7(6) . . ?
S2B S1A C1A 75.3(6) . . ?
S3B S1A C1B 133.8(6) . . ?
S2B S1A C1B 55.7(4) . . ?
C1A S1A C1B 19.7(5) . . ?
S3B S1A S2A 56.4(6) . . ?
S2B S1A S2A 40.7(3) . . ?
C1A S1A S2A 103.9(6) . . ?
C1B S1A S2A 87.0(5) . . ?
S2B S2A C3A 134.1(7) . . ?
S2B S2A S3B 75.0(5) . . ?
C3A S2A S3B 79.6(7) . . ?
S2B S2A C3B 117.5(7) . . ?
C3A S2A C3B 24.7(6) . . ?
S3B S2A C3B 54.9(5) . . ?
S2B S2A S1A 44.5(4) . . ?
C3A S2A S1A 102.1(7) . . ?
S3B S2A S1A 30.6(2) . . ?
C3B S2A S1A 78.7(6) . . ?
S1A S3B C3B 133.7(7) . . ?
S1A S3B S2A 93.0(7) . . ?
C3B S3B S2A 69.6(8) . . ?
S1A S3B S2B 49.6(6) . . ?
C3B S3B S2B 104.2(8) . . ?
S2A S3B S2B 43.5(3) . . ?
S1A S3B C3A 126.2(7) . . ?
C3B S3B C3A 19.7(8) . . ?
S2A S3B C3A 49.9(5) . . ?
S2B S3B C3A 86.8(6) . . ?
S2A S2B S1A 94.8(6) . . ?
S2A S2B C1B 134.2(5) . . ?
S1A S2B C1B 77.9(6) . . ?
S2A S2B S3B 61.5(4) . . ?
S1A S2B S3B 33.5(3) . . ?
C1B S2B S3B 103.6(7) . . ?
S2A S2B C1A 128.9(6) . . ?
S1A S2B C1A 58.7(5) . . ?
C1B S2B C1A 19.2(6) . . ?
S3B S2B C1A 85.4(6) . . ?
N5A N5B C3B 93(3) . . ?
N5A N5B N4 69.2(18) . . ?
C3B N5B N4 103.9(13) . . ?
N5A N5B C3A 59(2) . . ?
C3B N5B C3A 33.5(9) . . ?
N4 N5B C3A 90.8(11) . . ?
N5B N5A C3A 89(3) . . ?
N5B N5A N4 77(2) . . ?
C3A N5A N4 103.6(14) . . ?
N5B N5A C3B 57(2) . . ?
C3A N5A C3B 32.1(10) . . ?
N4 N5A C3B 94.3(12) . . ?

_refine_diff_density_max         0.799
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.125

_shelxl_version_number           2014-3

