# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_2016-4-2-20160325-28-1a-m1
_database_code_depnum_ccdc_archive 'CCDC 1870101'
_audit_update_record             
;
2018-09-27 deposited with the CCDC.
2019-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H4 N8 O4 Zn'
_chemical_formula_weight         269.50

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.2940(3)
_cell_length_b                   10.6563(7)
_cell_length_c                   5.5677(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.069(5)
_cell_angle_gamma                90
_cell_volume                     371.97(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    740
_cell_measurement_theta_min      4.134
_cell_measurement_theta_max      27.653

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.406
_exptl_crystal_F_000             268
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    3.319
_shelx_estimated_absorpt_T_min   0.529
_shelx_estimated_absorpt_T_max   0.586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1559
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.771
_diffrn_reflns_theta_max         28.922
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             849
_reflns_number_gt                687
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0746P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         849
_refine_ls_number_parameters     76
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.114
_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_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
C1 C 0.4783(6) 0.4623(4) 0.6010(8) 0.0170(8) Uani 1 1 d . . . . .
N1 N 0.2914(5) 0.4453(3) 0.6886(6) 0.0191(7) Uani 1 1 d . . . . .
N2 N 0.3278(5) 0.3721(3) 0.8833(7) 0.0233(8) Uani 1 1 d . . . . .
N3 N 0.5304(5) 0.3415(4) 0.9173(7) 0.0226(8) Uani 1 1 d . . . . .
N4 N 0.6263(5) 0.3980(3) 0.7397(6) 0.0160(7) Uani 1 1 d . . . . .
O1 O 0.8315(4) 0.3839(3) 0.7202(6) 0.0248(7) Uani 1 1 d . . . . .
O2 O 0.9718(5) 0.6487(3) 0.7388(6) 0.0280(8) Uani 1 1 d D . . . .
H1W H 1.047(7) 0.714(4) 0.742(9) 0.042 Uiso 1 1 d D U . . .
H2W H 0.920(8) 0.635(5) 0.862(6) 0.042 Uiso 1 1 d D U . . .
Zn1 Zn 1.0000 0.5000 0.5000 0.0175(3) Uani 1 2 d S . P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0127(19) 0.0197(18) 0.018(2) -0.0007(18) 0.0004(15) -0.0003(17)
N1 0.0116(16) 0.0254(18) 0.0203(19) 0.0026(16) 0.0020(13) -0.0016(14)
N2 0.0147(17) 0.0310(19) 0.024(2) 0.0053(15) 0.0019(14) -0.0007(15)
N3 0.0166(17) 0.0269(18) 0.025(2) 0.0066(16) 0.0032(14) 0.0008(15)
N4 0.0119(15) 0.0185(16) 0.0173(18) 0.0016(14) -0.0007(12) -0.0005(13)
O1 0.0100(13) 0.0299(16) 0.0347(19) 0.0095(14) 0.0034(12) 0.0029(12)
O2 0.0324(19) 0.0254(15) 0.027(2) -0.0058(14) 0.0096(14) -0.0055(15)
Zn1 0.0100(4) 0.0206(4) 0.0218(5) 0.0017(3) 0.0013(3) 0.0004(2)

_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 N1 1.325(5) . ?
C1 N4 1.344(5) . ?
C1 C1 1.428(9) 3_666 ?
N1 N2 1.338(5) . ?
N1 Zn1 2.114(3) 1_455 ?
N2 N3 1.313(4) . ?
N3 N4 1.346(5) . ?
N4 O1 1.314(4) . ?
O1 Zn1 2.095(3) . ?
O2 Zn1 2.086(3) . ?
O2 H1W 0.84(2) . ?
O2 H2W 0.80(2) . ?
Zn1 O1 2.095(3) 3_766 ?
Zn1 O2 2.086(3) 3_766 ?
Zn1 N1 2.114(3) 3_666 ?
Zn1 N1 2.114(3) 1_655 ?

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
N1 C1 N4 108.2(4) . . ?
N1 C1 C1 127.2(5) . 3_666 ?
N4 C1 C1 124.6(5) . 3_666 ?
C1 N1 N2 106.5(3) . . ?
C1 N1 Zn1 122.6(3) . 1_455 ?
N2 N1 Zn1 129.9(2) . 1_455 ?
N3 N2 N1 110.9(3) . . ?
N2 N3 N4 106.0(3) . . ?
O1 N4 C1 130.3(3) . . ?
O1 N4 N3 121.2(3) . . ?
C1 N4 N3 108.5(3) . . ?
N4 O1 Zn1 122.2(2) . . ?
Zn1 O2 H1W 124(4) . . ?
Zn1 O2 H2W 118(4) . . ?
H1W O2 H2W 114(5) . . ?
O1 Zn1 O1 180.00(13) . 3_766 ?
O1 Zn1 O2 89.97(12) . . ?
O1 Zn1 O2 90.03(12) 3_766 . ?
O1 Zn1 O2 90.03(12) . 3_766 ?
O1 Zn1 O2 89.97(12) 3_766 3_766 ?
O2 Zn1 O2 180.0 . 3_766 ?
O1 Zn1 N1 89.53(12) . 3_666 ?
O1 Zn1 N1 90.47(12) 3_766 3_666 ?
O2 Zn1 N1 89.31(14) . 3_666 ?
O2 Zn1 N1 90.69(14) 3_766 3_666 ?
O1 Zn1 N1 90.47(12) . 1_655 ?
O1 Zn1 N1 89.53(12) 3_766 1_655 ?
O2 Zn1 N1 90.69(14) . 1_655 ?
O2 Zn1 N1 89.31(14) 3_766 1_655 ?
N1 Zn1 N1 180.0 3_666 1_655 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 C1 N1 N2 1.0(5) . . . . ?
C1 C1 N1 N2 -177.5(6) 3_666 . . . ?
N4 C1 N1 Zn1 -168.8(3) . . . 1_455 ?
C1 C1 N1 Zn1 12.6(8) 3_666 . . 1_455 ?
C1 N1 N2 N3 -1.0(5) . . . . ?
Zn1 N1 N2 N3 167.9(3) 1_455 . . . ?
N1 N2 N3 N4 0.6(5) . . . . ?
N1 C1 N4 O1 178.0(4) . . . . ?
C1 C1 N4 O1 -3.4(8) 3_666 . . . ?
N1 C1 N4 N3 -0.7(5) . . . . ?
C1 C1 N4 N3 177.9(5) 3_666 . . . ?
N2 N3 N4 O1 -178.7(3) . . . . ?
N2 N3 N4 C1 0.1(5) . . . . ?
C1 N4 O1 Zn1 15.7(6) . . . . ?
N3 N4 O1 Zn1 -165.8(3) . . . . ?

_refine_diff_density_max         0.525
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.222

_shelx_res_file                  
;

    2016-4-2-20160325-28-1a-m1.res created by SHELXL-2014/7

TITL 2016-4-2-20160325-28-1a-m1_a.res in P2(1)/c
CELL 0.71073 6.294042 10.656342 5.567708 90 95.0693 90
ZERR 2 0.000303 0.000652 0.000399 0 0.005 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C  H  N  O  Zn
UNIT 4 8 16 8 2
L.S. 20
ACTA
BOND $H
FMAP 2
PLAN 20
LIST 6
size 0.22 0.2 0.18
MORE -1
CONF
DFIX 0.84 0.02 O2 H1W O2 H2W
DANG 0.02 1.39 H1W H2W
WGHT    0.074600
FVAR       1.15156
C1    1    0.478288    0.462339    0.601049    11.00000    0.01272    0.01970 =
         0.01832   -0.00066    0.00044   -0.00030
N1    3    0.291430    0.445257    0.688616    11.00000    0.01156    0.02541 =
         0.02030    0.00264    0.00198   -0.00162
N2    3    0.327819    0.372077    0.883276    11.00000    0.01466    0.03096 =
         0.02443    0.00534    0.00188   -0.00075
N3    3    0.530365    0.341476    0.917319    11.00000    0.01661    0.02686 =
         0.02466    0.00660    0.00324    0.00084
N4    3    0.626334    0.398035    0.739682    11.00000    0.01193    0.01848 =
         0.01728    0.00164   -0.00068   -0.00054
O1    4    0.831511    0.383923    0.720196    11.00000    0.01001    0.02989 =
         0.03474    0.00952    0.00345    0.00292
O2    4    0.971785    0.648717    0.738817    11.00000    0.03242    0.02541 =
         0.02736   -0.00585    0.00959   -0.00546
H1W   2    1.047478    0.713948    0.742247    11.00000   -1.50000
H2W   2    0.919578    0.634774    0.862189    11.00000   -1.50000
ZN1   5    1.000000    0.500000    0.500000    10.50000    0.01003    0.02063 =
         0.02180    0.00166    0.00126    0.00042
HKLF 4

REM  2016-4-2-20160325-28-1a-m1_a.res in P2(1)/c
REM R1 =  0.0412 for     687 Fo > 4sig(Fo)  and  0.0533 for all     849 data
REM     76 parameters refined using      3 restraints

END

WGHT      0.0666      0.0000

REM Highest difference peak  0.525,  deepest hole -0.786,  1-sigma level  0.222
Q1    1   0.8008  0.2853  0.5300  11.00000  0.05    0.52
Q2    1   1.2160  0.7211  0.6700  11.00000  0.05    0.52
Q3    1   0.9954  0.7422  0.4999  11.00000  0.05    0.52
Q4    1   0.5429  0.2587  0.8480  11.00000  0.05    0.49
Q5    1   0.9942  0.3549  0.7194  11.00000  0.05    0.48
Q6    1   0.5614  0.3543  0.8539  11.00000  0.05    0.46
Q7    1   0.9160  0.7388  0.5792  11.00000  0.05    0.45
Q8    1   0.2355  0.2794  0.8888  11.00000  0.05    0.45
Q9    1   0.6751  0.2762  0.9231  11.00000  0.05    0.45
Q10   1   0.3430  0.2565  0.6851  11.00000  0.05    0.44
Q11   1   0.9756  0.7742  0.7183  11.00000  0.05    0.44
Q12   1   0.2353  0.3019  0.6481  11.00000  0.05    0.44
Q13   1   0.6004  0.2446  1.0481  11.00000  0.05    0.44
Q14   1   0.8352  0.7435  0.9300  11.00000  0.05    0.43
Q15   1   1.3261  0.7339  0.7777  11.00000  0.05    0.43
Q16   1   0.3725  0.2262  0.8239  11.00000  0.05    0.41
Q17   1   0.8158  0.6230  0.7065  11.00000  0.05    0.41
Q18   1   1.0356  0.6763  0.7104  11.00000  0.05    0.40
Q19   1   1.1710  0.7804  0.7845  11.00000  0.05    0.40
Q20   1   0.5175  0.2942  0.9983  11.00000  0.05    0.40
;
_shelx_res_checksum              72250
