# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_170327-39
_database_code_depnum_ccdc_archive 'CCDC 1549823'
_audit_update_record             
;
2017-05-13 deposited with the CCDC.
2017-09-22 downloaded from the CCDC.
;
_audit_creation_date             2017-03-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 N5 O3 Zn'
_chemical_formula_sum            'C12 H13 N5 O3 Zn'
_chemical_formula_weight         340.64
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Zn'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.0423(4)
_cell_length_b                   10.5269(4)
_cell_length_c                   32.6069(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2760.5(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2069
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.1030
_cell_measurement_theta_min      3.7450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.797
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76344
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0890
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6203
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.339
_diffrn_reflns_theta_min         3.248
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9737
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  71.00   1.00   50.00    --   18.81 178.00 120.00   36
  2  ω    -14.00  44.00   1.00   50.00    --   18.81 -99.00 -60.00   58
  3  ω    -15.00  40.00   1.00   50.00    --   18.81 -37.00  30.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0071815000
_diffrn_orient_matrix_UB_12      0.0249992000
_diffrn_orient_matrix_UB_13      0.0201255000
_diffrn_orient_matrix_UB_21      -0.0660394000
_diffrn_orient_matrix_UB_22      0.0427260000
_diffrn_orient_matrix_UB_23      -0.0041241000
_diffrn_orient_matrix_UB_31      -0.0580261000
_diffrn_orient_matrix_UB_32      -0.0457681000
_diffrn_orient_matrix_UB_33      0.0071098000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1727
_reflns_number_total             2521
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2521
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      0.951
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0575
_refine_ls_wR_factor_ref         0.0678
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.55378(5) 0.70014(4) 0.37547(2) 0.03113(15) Uani 1 1 d . . . . .
O1 O 0.4936(3) 0.7151(3) 0.43225(8) 0.0463(7) Uani 1 1 d . . . . .
O2 O 0.2906(5) 0.5842(3) 0.41602(9) 0.0908(13) Uani 1 1 d . . . . .
O3 O 0.3934(3) 0.6914(2) 0.32944(7) 0.0349(6) Uani 1 1 d . . . . .
N1 N 0.1723(4) 0.6342(3) 0.63756(8) 0.0301(7) Uani 1 1 d . . . . .
N2 N 0.1579(4) 0.5765(3) 0.67468(9) 0.0361(8) Uani 1 1 d . . . . .
N3 N 0.2309(4) 0.4668(3) 0.67323(9) 0.0384(8) Uani 1 1 d . . . . .
N4 N 0.2964(4) 0.4499(3) 0.63490(9) 0.0321(8) Uani 1 1 d . . . . .
N5 N 0.1655(4) 0.7442(3) 0.29396(10) 0.0429(9) Uani 1 1 d . . . . .
C1 C 0.3745(6) 0.6379(4) 0.44123(12) 0.0408(11) Uani 1 1 d . . . . .
C2 C 0.3451(4) 0.6185(3) 0.48673(11) 0.0287(9) Uani 1 1 d . . . . .
C3 C 0.4302(4) 0.6884(3) 0.51557(11) 0.0353(10) Uani 1 1 d . . . . .
H3 H 0.5066 0.7494 0.5071 0.042 Uiso 1 1 calc R . . . .
C4 C 0.4030(4) 0.6686(3) 0.55717(11) 0.0369(10) Uani 1 1 d . . . . .
H4 H 0.4591 0.7174 0.5765 0.044 Uiso 1 1 calc R . . . .
C5 C 0.2919(4) 0.5757(3) 0.56970(11) 0.0294(9) Uani 1 1 d . . . . .
C6 C 0.2102(5) 0.5045(3) 0.54091(11) 0.0382(10) Uani 1 1 d . . . . .
H6 H 0.1367 0.4415 0.5493 0.046 Uiso 1 1 calc R . . . .
C7 C 0.2361(5) 0.5257(3) 0.49930(12) 0.0400(10) Uani 1 1 d . . . . .
H7 H 0.1796 0.4771 0.4800 0.048 Uiso 1 1 calc R . . . .
C8 C 0.2579(4) 0.5541(3) 0.61397(11) 0.0261(9) Uani 1 1 d . . . . .
C9 C 0.2695(5) 0.7635(4) 0.32505(12) 0.0355(10) Uani 1 1 d . . . . .
C10 C 0.2389(5) 0.8694(4) 0.35450(12) 0.0530(12) Uani 1 1 d . . . . .
H10A H 0.3119 0.8606 0.3776 0.079 Uiso 1 1 calc GR . . . .
H10B H 0.1255 0.8666 0.3636 0.079 Uiso 1 1 calc GR . . . .
H10C H 0.2598 0.9492 0.3412 0.079 Uiso 1 1 calc GR . . . .
C11 C 0.1837(5) 0.6339(4) 0.26759(13) 0.0604(13) Uani 1 1 d . . . . .
H11A H 0.2921 0.5975 0.2714 0.091 Uiso 1 1 calc GR . . . .
H11B H 0.1707 0.6591 0.2395 0.091 Uiso 1 1 calc GR . . . .
H11C H 0.1005 0.5721 0.2744 0.091 Uiso 1 1 calc GR . . . .
C12 C 0.0197(5) 0.8230(4) 0.28559(14) 0.0711(15) Uani 1 1 d . . . . .
H12A H -0.0789 0.7789 0.2942 0.107 Uiso 1 1 calc GR . . . .
H12B H 0.0134 0.8403 0.2567 0.107 Uiso 1 1 calc GR . . . .
H12C H 0.0289 0.9016 0.3004 0.107 Uiso 1 1 calc GR . . . .


_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 O1 1.920(2) . ?
Zn1 O3 1.981(2) . ?
Zn1 N1 2.033(3) 4_566 ?
Zn1 N4 2.015(3) 5_666 ?
O1 C1 1.289(4) . ?
O2 C1 1.205(5) . ?
O3 C9 1.261(4) . ?
N1 Zn1 2.033(3) 4_466 ?
N1 N2 1.359(4) . ?
N1 C8 1.333(4) . ?
N2 N3 1.296(4) . ?
N3 N4 1.368(4) . ?
N4 Zn1 2.015(3) 5_666 ?
N4 C8 1.328(4) . ?
N5 C9 1.330(5) . ?
N5 C11 1.452(4) . ?
N5 C12 1.462(4) . ?
C1 C2 1.516(5) . ?
C2 C3 1.376(5) . ?
C2 C7 1.375(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(5) . ?
C5 C6 1.369(5) . ?
C5 C8 1.487(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.391(5) . ?
C7 H7 0.9300 . ?
C9 C10 1.492(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
O1 Zn1 O3 124.76(11) . . ?
O1 Zn1 N1 104.44(12) . 4_566 ?
O1 Zn1 N4 112.13(12) . 5_666 ?
O3 Zn1 N1 100.78(10) . 4_566 ?
O3 Zn1 N4 103.05(11) . 5_666 ?
N4 Zn1 N1 110.92(11) 5_666 4_566 ?
C1 O1 Zn1 110.8(3) . . ?
C9 O3 Zn1 124.9(3) . . ?
N2 N1 Zn1 122.0(2) . 4_466 ?
C8 N1 Zn1 131.6(2) . 4_466 ?
C8 N1 N2 106.0(3) . . ?
N3 N2 N1 109.1(3) . . ?
N2 N3 N4 108.9(3) . . ?
N3 N4 Zn1 119.1(2) . 5_666 ?
C8 N4 Zn1 134.5(2) . 5_666 ?
C8 N4 N3 105.8(3) . . ?
C9 N5 C11 120.7(3) . . ?
C9 N5 C12 124.0(4) . . ?
C11 N5 C12 115.1(3) . . ?
O1 C1 C2 115.0(4) . . ?
O2 C1 O1 123.9(4) . . ?
O2 C1 C2 121.1(4) . . ?
C3 C2 C1 121.2(4) . . ?
C7 C2 C1 119.2(4) . . ?
C7 C2 C3 119.6(3) . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C8 120.9(3) . . ?
C6 C5 C4 119.6(3) . . ?
C6 C5 C8 119.5(3) . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.6(4) . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 120.0(4) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
N1 C8 C5 123.9(3) . . ?
N4 C8 N1 110.3(3) . . ?
N4 C8 C5 125.6(3) . . ?
O3 C9 N5 119.4(4) . . ?
O3 C9 C10 120.5(4) . . ?
N5 C9 C10 120.1(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N5 C11 H11A 109.5 . . ?
N5 C11 H11B 109.5 . . ?
N5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N5 C12 H12A 109.5 . . ?
N5 C12 H12B 109.5 . . ?
N5 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_olex2_date_sample_data_collection 2017-03-28
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.201
_oxdiff_exptl_absorpt_empirical_full_min 0.851
