# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_sun-12
_database_code_depnum_ccdc_archive 'CCDC 1497755'
loop_
_audit_author_name
_audit_author_address
'Yayong Sun'
;Fujian Institute of Research on The Structure
China
;
_audit_update_record             
;
2018-12-31 deposited with the CCDC.	2019-12-02 downloaded from the CCDC.
;
_audit_creation_date             2015-12-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C7 H8 N2 O3 P Zn'
_chemical_formula_sum            'C7 H8 N2 O3 P Zn'
_chemical_formula_weight         264.49
_chemical_melting_point          ?
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'
P P 0.1023 0.0942 '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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   8.8182(5)
_cell_length_b                   10.1110(4)
_cell_length_c                   21.4930(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1916.33(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2216
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6350
_cell_measurement_theta_min      2.9810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.710
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70975
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.834
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5731
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.988
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1366
_reflns_number_total             1686
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
'L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation (2013)'
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         1686
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.030
_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)+(0.0370P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0782
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C1(H1A), C7(H7), C3(H3), C2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.29538(4) 0.41227(3) 0.47969(2) 0.02110(16) Uani 1 1 d . . . . .
P1 P 0.56828(10) 0.31791(8) 0.56402(4) 0.0205(2) Uani 1 1 d . . . A -1
O1 O 0.4805(3) 0.3192(2) 0.50331(10) 0.0302(6) Uani 1 1 d . . . . .
N1 N 0.1955(3) 0.4761(3) 0.55777(13) 0.0272(7) Uani 1 1 d . . . . .
N2 N 0.0520(3) 0.4832(3) 0.64094(11) 0.0261(7) Uani 1 1 d . . . . .
C5 C -0.0368(4) 0.3271(4) 0.72120(14) 0.0294(8) Uani 1 1 d . . . . .
C6 C -0.0737(5) 0.2070(4) 0.69405(17) 0.0395(10) Uani 1 1 d . . . . .
H6 H -0.1241 0.2064 0.6560 0.047 Uiso 1 1 calc R U . . .
C1 C 0.0692(4) 0.4324(3) 0.58362(15) 0.0290(8) Uani 1 1 d . . . . .
H1A H 0.0015 0.3744 0.5647 0.035 Uiso 1 1 calc R U . . .
C4 C -0.0714(4) 0.4521(4) 0.68410(15) 0.0345(9) Uani 1 1 d . . . . .
H4A H -0.1647 0.4398 0.6609 0.041 Uiso 1 1 calc R U . . .
H4B H -0.0859 0.5256 0.7125 0.041 Uiso 1 1 calc R U . . .
C7 C -0.0376(5) 0.0885(4) 0.72197(17) 0.0452(11) Uani 1 1 d . . . . .
H7 H -0.0639 0.0090 0.7030 0.054 Uiso 1 1 calc R U . . .
C3 C 0.1746(5) 0.5628(4) 0.65202(16) 0.0339(9) Uani 1 1 d . . . . .
H3 H 0.1936 0.6110 0.6880 0.041 Uiso 1 1 calc R U . . .
C2 C 0.2629(5) 0.5577(4) 0.60050(17) 0.0345(9) Uani 1 1 d . . . . .
H2 H 0.3542 0.6022 0.5950 0.041 Uiso 1 1 calc R U . . .
H1 H 0.466(4) 0.310(3) 0.6106(13) 0.023(8) Uiso 1 1 d . . . . .
O2 O 0.6513(3) 0.4457(2) 0.57643(11) 0.0350(6) Uani 1 1 d . . . . .
O3 O 0.6693(3) 0.1985(2) 0.57034(11) 0.0363(6) Uani 1 1 d . . . . .

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
Zn1 0.0222(3) 0.0221(2) 0.0189(2) -0.00062(15) 0.00163(16) 0.00063(17)
P1 0.0203(5) 0.0190(4) 0.0222(5) 0.0022(3) 0.0026(4) 0.0015(4)
O1 0.0274(15) 0.0351(13) 0.0280(13) -0.0065(10) -0.0063(11) 0.0109(12)
N1 0.0284(19) 0.0298(16) 0.0233(16) -0.0034(13) 0.0019(13) 0.0032(14)
N2 0.0222(18) 0.0396(17) 0.0166(14) 0.0002(12) 0.0014(12) 0.0060(14)
C5 0.019(2) 0.051(2) 0.0181(17) -0.0006(15) 0.0030(15) 0.0015(18)
C6 0.027(2) 0.070(3) 0.0223(19) -0.0057(19) -0.0021(16) -0.003(2)
C1 0.032(2) 0.0351(19) 0.0202(18) -0.0044(15) 0.0011(16) 0.0025(17)
C4 0.027(2) 0.057(2) 0.0199(18) -0.0003(16) 0.0005(16) 0.0072(19)
C7 0.042(3) 0.052(2) 0.041(2) -0.0026(17) 0.008(2) -0.004(2)
C3 0.034(2) 0.043(2) 0.024(2) -0.0094(16) -0.0012(17) 0.0003(19)
C2 0.032(2) 0.041(2) 0.030(2) -0.0044(18) 0.0009(18) -0.0032(19)
O2 0.0503(18) 0.0269(12) 0.0277(13) 0.0037(10) -0.0042(12) -0.0144(13)
O3 0.0421(17) 0.0317(13) 0.0351(15) 0.0026(11) 0.0001(12) 0.0209(12)

_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 1.951(2) . ?
Zn1 N1 2.002(3) . ?
Zn1 O2 1.933(2) 5_666 ?
Zn1 O3 1.910(2) 3_456 ?
P1 O1 1.517(2) . ?
P1 O2 1.509(2) . ?
P1 O3 1.507(2) . ?
N1 C1 1.320(4) . ?
N1 C2 1.370(4) . ?
N2 C1 1.343(4) . ?
N2 C4 1.464(4) . ?
N2 C3 1.368(5) . ?
C5 C5 1.398(6) 4_556 ?
C5 C6 1.386(5) . ?
C5 C4 1.525(5) . ?
C6 C7 1.378(5) . ?
C7 C7 1.375(8) 4_556 ?
C3 C2 1.355(5) . ?
O2 Zn1 1.933(2) 5_666 ?
O3 Zn1 1.910(2) 3_556 ?

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 N1 107.78(11) . . ?
O2 Zn1 O1 108.49(11) 5_666 . ?
O2 Zn1 N1 112.98(11) 5_666 . ?
O3 Zn1 O1 110.53(10) 3_456 . ?
O3 Zn1 N1 113.89(11) 3_456 . ?
O3 Zn1 O2 103.05(10) 3_456 5_666 ?
O2 P1 O1 113.10(13) . . ?
O3 P1 O1 112.72(13) . . ?
O3 P1 O2 112.52(16) . . ?
P1 O1 Zn1 130.90(14) . . ?
C1 N1 Zn1 128.0(2) . . ?
C1 N1 C2 106.6(3) . . ?
C2 N1 Zn1 124.4(2) . . ?
C1 N2 C4 125.7(3) . . ?
C1 N2 C3 107.2(3) . . ?
C3 N2 C4 127.1(3) . . ?
C5 C5 C4 123.8(2) 4_556 . ?
C6 C5 C5 118.8(2) . 4_556 ?
C6 C5 C4 117.3(3) . . ?
C7 C6 C5 121.6(3) . . ?
N1 C1 N2 110.7(3) . . ?
N2 C4 C5 111.1(3) . . ?
C7 C7 C6 119.5(2) 4_556 . ?
C2 C3 N2 106.8(3) . . ?
C3 C2 N1 108.7(4) . . ?
P1 O2 Zn1 130.06(14) . 5_666 ?
P1 O3 Zn1 139.78(15) . 3_556 ?

_shelx_res_file                  
;
TITL
CELL 0.71073 8.8182 10.111 21.493 90 90 90
ZERR 8 0.0005 0.0004 0.0009 0 0 0
LATT 1
SYMM 0.5-X,0.5-Y,0.5+Z
SYMM 0.5+X,0.5-Y,-Z
SYMM -X,+Y,0.5-Z

SFAC C H N O P Zn
UNIT 56 64 16 24 8 8

L.S. 20 0 0
PLAN  5
fmap 2 53
acta
OMIT -3 50
REM <HKL>C:/Users/Administrator/Desktop/n-hnsf-12--tmp/sun-12.hkl</HKL>

WGHT    0.037000
FVAR       0.36465
ZN1   6    0.295379    0.412271    0.479690    11.00000    0.02225    0.02214 =
         0.01890   -0.00062    0.00163    0.00063
PART -1
P1    5    0.568284    0.317913    0.564023    11.00000    0.02030    0.01897 =
         0.02220    0.00220    0.00261    0.00153
PART 0
O1    4    0.480482    0.319220    0.503308    11.00000    0.02744    0.03515 =
         0.02798   -0.00647   -0.00632    0.01090
N1    3    0.195479    0.476091    0.557767    11.00000    0.02841    0.02979 =
         0.02328   -0.00339    0.00186    0.00318
N2    3    0.052018    0.483224    0.640936    11.00000    0.02219    0.03961 =
         0.01663    0.00018    0.00142    0.00597
C5    1   -0.036779    0.327076    0.721195    11.00000    0.01928    0.05100 =
         0.01805   -0.00060    0.00301    0.00154
C6    1   -0.073708    0.207012    0.694052    11.00000    0.02659    0.06972 =
         0.02233   -0.00569   -0.00214   -0.00253
AFIX  43
H6    2   -0.124119    0.206437    0.656046    11.00000   -1.20000
AFIX   0
C1    1    0.069232    0.432423    0.583618    11.00000    0.03166    0.03513 =
         0.02024   -0.00438    0.00113    0.00255
AFIX  43
H1A   2    0.001512    0.374448    0.564737    11.00000   -1.20000
AFIX   0
C4    1   -0.071368    0.452103    0.684103    11.00000    0.02710    0.05658 =
         0.01993   -0.00031    0.00051    0.00716
AFIX  23
H4A   2   -0.164681    0.439839    0.660913    11.00000   -1.20000
H4B   2   -0.085887    0.525578    0.712503    11.00000   -1.20000
AFIX   0
C7    1   -0.037595    0.088459    0.721974    11.00000    0.04216    0.05226 =
         0.04123   -0.00259    0.00818   -0.00382
AFIX  43
H7    2   -0.063885    0.008991    0.703043    11.00000   -1.20000
AFIX   0
C3    1    0.174600    0.562756    0.652018    11.00000    0.03409    0.04328 =
         0.02434   -0.00938   -0.00123    0.00034
AFIX  43
H3    2    0.193643    0.611044    0.688007    11.00000   -1.20000
AFIX   0
C2    1    0.262915    0.557656    0.600495    11.00000    0.03242    0.04062 =
         0.03040   -0.00441    0.00087   -0.00324
AFIX  43
H2    2    0.354239    0.602171    0.595033    11.00000   -1.20000
AFIX   0
H1    2    0.465893    0.309828    0.610601    11.00000    0.02268
O2    4    0.651347    0.445692    0.576435    11.00000    0.05027    0.02688 =
         0.02773    0.00370   -0.00418   -0.01445
O3    4    0.669331    0.198509    0.570341    11.00000    0.04211    0.03174 =
         0.03510    0.00258    0.00011    0.02093
HKLF 4

REM
REM R1 =  0.0317 for    1366 Fo > 4sig(Fo)  and  0.0442 for all    1686 data
REM    131 parameters refined using      0 restraints

END

WGHT      0.0367      0.0000

REM Highest difference peak  0.452,  deepest hole -0.361,  1-sigma level  0.086
Q1    1   0.4210  0.4008  0.4822  11.00000  0.05    0.45
Q2    1   0.3811  0.3020  0.5136  11.00000  0.05    0.37
Q3    1   0.0038  0.4426  0.6602  11.00000  0.05    0.33
Q4    1   0.4839  0.3559  0.5266  11.00000  0.05    0.32
Q5    1   0.7424  0.2562  0.5620  11.00000  0.05    0.31
;
_shelx_res_checksum              61300
####################################################################### 
# 
# 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_sun-28
_database_code_depnum_ccdc_archive 'CCDC 1965529'
loop_
_audit_author_name
_audit_author_address
'Yayong Sun'
;Fujian Institute of Research on The Structure
China
;
_audit_update_record             
;
2019-11-13 deposited with the CCDC.	2019-12-02 downloaded from the CCDC.
;
_audit_creation_date             2019-11-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H9 N2 O3 P Zn'
_chemical_formula_sum            'C8 H9 N2 O3 P Zn'
_chemical_formula_weight         277.51
_chemical_melting_point          ?
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'
P P 0.1023 0.0942 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   5.2103(2)
_cell_length_b                   11.7634(5)
_cell_length_c                   17.4168(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.315(4)
_cell_angle_gamma                90
_cell_volume                     1053.41(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5989
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3800
_cell_measurement_theta_min      2.9120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.470
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Rod
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11248
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.644
_diffrn_reflns_theta_min         2.370
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2462
_reflns_number_total             2647
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         2.802
_refine_diff_density_min         -2.537
_refine_diff_density_rms         0.449
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2647
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1774
_refine_ls_R_factor_gt           0.1745
_refine_ls_restrained_S_all      1.156
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0810P)²+137.1431P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4731
_refine_ls_wR_factor_ref         0.4740
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2), C8(H8), C1(H1)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.1502(5) 0.5705(2) 0.41659(13) 0.0263(7) Uani 1 1 d . . . . .
P1 P 0.3033(10) 0.3436(4) 0.5015(3) 0.0235(10) Uani 1 1 d . . . . .
O3 O 0.593(3) 0.3444(13) 0.5141(9) 0.033(3) Uani 1 1 d . . . . .
O1 O 0.192(3) 0.4072(12) 0.4290(9) 0.036(4) Uani 1 1 d . . . . .
O2 O 0.201(3) 0.3864(17) 0.5739(8) 0.041(4) Uani 1 1 d . . . . .
C7 C -0.019(4) 0.4859(19) 0.0768(10) 0.030(4) Uani 1 1 d . . . . .
H7 H -0.027400 0.474408 0.129134 0.036 Uiso 1 1 calc R . . . .
C3 C 0.291(4) 0.5847(16) 0.2548(11) 0.028(4) Uani 1 1 d . . . . .
C6 C 0.161(5) 0.5632(18) 0.0563(13) 0.033(4) Uani 1 1 d . . . . .
N2 N 0.248(4) 0.6477(17) 0.1890(11) 0.038(4) Uani 1 1 d . . . . .
C5 C 0.341(5) 0.633(2) 0.1144(13) 0.041(5) Uani 1 1 d . . . . .
H5A H 0.510254 0.596235 0.123897 0.049 Uiso 1 1 calc R . . . .
H5B H 0.363499 0.707120 0.092178 0.049 Uiso 1 1 calc R . . . .
C2 C 0.069(6) 0.728(2) 0.2031(13) 0.044(6) Uani 1 1 d . . . . .
H2 H -0.002385 0.784747 0.168740 0.053 Uiso 1 1 calc R . . . .
C4 C 0.473(6) 0.4857(19) 0.2647(13) 0.042(6) Uani 1 1 d . . . . .
H4A H 0.448038 0.440770 0.218029 0.063 Uiso 1 1 calc GR . . . .
H4B H 0.439515 0.439918 0.307588 0.063 Uiso 1 1 calc GR . . . .
H4C H 0.649438 0.512668 0.274777 0.063 Uiso 1 1 calc GR . . . .
C8 C 0.184(5) 0.574(2) -0.0212(12) 0.039(5) Uani 1 1 d . . . . .
H8 H 0.310176 0.621858 -0.035905 0.047 Uiso 1 1 calc R . . . .
C1 C 0.014(6) 0.711(3) 0.2759(13) 0.053(7) Uani 1 1 d . . . . .
H1 H -0.099081 0.753144 0.300605 0.064 Uiso 1 1 calc R . . . .
N1 N 0.158(4) 0.6174(17) 0.3062(10) 0.033(4) Uani 1 1 d . . . . .

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
Zn1 0.0322(12) 0.0294(12) 0.0171(10) 0.0027(9) 0.0038(8) 0.0031(9)
P1 0.031(2) 0.017(2) 0.022(2) -0.0034(18) 0.0043(18) 0.0002(18)
O3 0.041(8) 0.029(7) 0.030(7) -0.009(6) 0.007(6) 0.001(6)
O1 0.063(10) 0.013(6) 0.029(7) -0.002(6) -0.005(7) 0.007(6)
O2 0.037(8) 0.079(13) 0.010(6) 0.011(7) 0.008(5) 0.016(8)
C7 0.048(12) 0.032(11) 0.011(8) 0.001(7) 0.007(8) -0.008(9)
C3 0.042(11) 0.020(9) 0.021(8) 0.001(7) 0.003(7) -0.013(8)
C6 0.046(12) 0.024(9) 0.033(10) -0.010(8) 0.015(9) -0.004(9)
N2 0.055(12) 0.031(10) 0.025(9) -0.011(8) 0.000(8) -0.012(8)
C5 0.045(13) 0.048(14) 0.031(11) 0.006(10) 0.007(9) -0.009(11)
C2 0.070(16) 0.040(13) 0.021(10) 0.013(9) -0.003(10) 0.012(12)
C4 0.076(17) 0.020(10) 0.027(11) -0.014(8) 0.003(11) 0.002(10)
C8 0.052(13) 0.044(13) 0.023(10) 0.005(9) 0.011(9) -0.008(11)
C1 0.072(18) 0.070(19) 0.017(10) 0.013(11) 0.004(11) 0.025(15)
N1 0.044(10) 0.036(10) 0.019(8) 0.009(7) 0.000(7) 0.004(8)

_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 1.929(15) 3_666 ?
Zn1 O1 1.941(14) . ?
Zn1 O2 1.933(15) 3_566 ?
Zn1 N1 2.007(17) . ?
P1 O3 1.491(16) . ?
P1 O1 1.502(15) . ?
P1 O2 1.530(15) . ?
C7 H7 0.9300 . ?
C7 C6 1.39(3) . ?
C7 C8 1.38(3) 3_565 ?
C3 N2 1.35(3) . ?
C3 C4 1.49(3) . ?
C3 N1 1.28(3) . ?
C6 C5 1.51(3) . ?
C6 C8 1.38(3) . ?
N2 C5 1.47(3) . ?
N2 C2 1.38(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C2 H2 0.9300 . ?
C2 C1 1.36(3) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C8 H8 0.9300 . ?
C1 H1 0.9300 . ?
C1 N1 1.39(3) . ?

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 113.0(7) 3_666 . ?
O3 Zn1 O2 112.3(7) 3_666 3_566 ?
O3 Zn1 N1 109.7(8) 3_666 . ?
O1 Zn1 N1 111.1(7) . . ?
O2 Zn1 O1 109.9(8) 3_566 . ?
O2 Zn1 N1 100.2(7) 3_566 . ?
O3 P1 O1 111.5(10) . . ?
O3 P1 O2 110.8(9) . . ?
O1 P1 O2 112.9(9) . . ?
P1 O3 Zn1 132.7(9) . 3_666 ?
P1 O1 Zn1 127.4(9) . . ?
P1 O2 Zn1 128.1(9) . 3_566 ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 3_565 . ?
C8 C7 C6 121.6(18) 3_565 . ?
N2 C3 C4 123(2) . . ?
N1 C3 N2 113(2) . . ?
N1 C3 C4 124.1(19) . . ?
C7 C6 C5 123.7(19) . . ?
C8 C6 C7 119(2) . . ?
C8 C6 C5 117(2) . . ?
C3 N2 C5 130(2) . . ?
C3 N2 C2 104.6(18) . . ?
C2 N2 C5 125(2) . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
N2 C5 C6 113.4(19) . . ?
N2 C5 H5A 108.9 . . ?
N2 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
N2 C2 H2 125.9 . . ?
C1 C2 N2 108(2) . . ?
C1 C2 H2 125.9 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C7 C8 H8 120.2 3_565 . ?
C6 C8 C7 120(2) . 3_565 ?
C6 C8 H8 120.2 . . ?
C2 C1 H1 126.5 . . ?
C2 C1 N1 107(2) . . ?
N1 C1 H1 126.5 . . ?
C3 N1 Zn1 133.4(15) . . ?
C3 N1 C1 107.1(18) . . ?
C1 N1 Zn1 119.3(16) . . ?

_shelx_res_file                  
;
TITL sun-28_a.res in P2(1)/c
    sun-28.res
    created by SHELXL-2018/1 at 16:47:35 on 13-Nov-2019
REM Old TITL P21/c
REM SHELXT solution in P2(1)/c
REM R1 0.225, Rweak 0.157, Alpha 0.187, Orientation as input
REM Formula found by SHELXT: C21 N2 O8 P2 Zn2
CELL 0.71073 5.2103 11.7634 17.4168 90 99.315 90
ZERR 4 0.0002 0.0005 0.0008 0 0.004 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O P Zn
UNIT 32 36 8 12 4 4

L.S. 25
PLAN  5
BOND $H
list 4
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\sun-28.hkl">
REM </olex2.extras>

WGHT    0.081000  137.143112
FVAR       0.70472
ZN1   6    0.150166    0.570493    0.416585    11.00000    0.03224    0.02940 =
         0.01714    0.00272    0.00382    0.00314
P1  5    0.303313    0.343592    0.501522    11.00000    0.03149    0.01664 =
         0.02226   -0.00343    0.00431    0.00018
O3    4    0.593336    0.344379    0.514133    11.00000    0.04057    0.02864 =
         0.02991   -0.00932    0.00686    0.00079
O1    4    0.191673    0.407214    0.429020    11.00000    0.06286    0.01298 =
         0.02868   -0.00167   -0.00469    0.00683
O2    4    0.201266    0.386439    0.573861    11.00000    0.03663    0.07855 =
         0.00983    0.01117    0.00786    0.01565
C7    1   -0.018592    0.485891    0.076794    11.00000    0.04793    0.03229 =
         0.01112    0.00143    0.00728   -0.00779
AFIX  43
H7    2   -0.027400    0.474408    0.129134    11.00000   -1.20000
AFIX   0
C3    1    0.291184    0.584669    0.254784    11.00000    0.04180    0.02007 =
         0.02088    0.00138    0.00250   -0.01292
C6    1    0.160885    0.563228    0.056310    11.00000    0.04611    0.02414 =
         0.03266   -0.00978    0.01533   -0.00416
N2    3    0.247680    0.647692    0.188996    11.00000    0.05497    0.03079 =
         0.02486   -0.01068    0.00001   -0.01176
C5    1    0.341274    0.632849    0.114391    11.00000    0.04493    0.04796 =
         0.03078    0.00625    0.00710   -0.00879
AFIX  23
H5A   2    0.510254    0.596235    0.123897    11.00000   -1.20000
H5B   2    0.363499    0.707120    0.092178    11.00000   -1.20000
AFIX   0
C2    1    0.068614    0.728225    0.203074    11.00000    0.06958    0.03960 =
         0.02077    0.01315   -0.00298    0.01214
AFIX  43
H2    2   -0.002385    0.784747    0.168740    11.00000   -1.20000
AFIX   0
C4    1    0.473334    0.485651    0.264679    11.00000    0.07649    0.02045 =
         0.02725   -0.01374    0.00283    0.00224
AFIX 137
H4A   2    0.448038    0.440770    0.218029    11.00000   -1.50000
H4B   2    0.439515    0.439918    0.307588    11.00000   -1.50000
H4C   2    0.649438    0.512668    0.274777    11.00000   -1.50000
AFIX   0
C8    1    0.184094    0.574277   -0.021199    11.00000    0.05244    0.04379 =
         0.02310    0.00523    0.01101   -0.00782
AFIX  43
H8    2    0.310176    0.621858   -0.035905    11.00000   -1.20000
AFIX   0
C1    1    0.013938    0.710625    0.275856    11.00000    0.07206    0.06994 =
         0.01739    0.01302    0.00399    0.02505
AFIX  43
H1    2   -0.099081    0.753144    0.300605    11.00000   -1.20000
AFIX   0
N1    3    0.158337    0.617399    0.306212    11.00000    0.04372    0.03604 =
         0.01893    0.00906   -0.00027    0.00402
HKLF 4




REM  sun-28_a.res in P2(1)/c
REM R1 =  0.1745 for    2462 Fo > 4sig(Fo)  and  0.1774 for all    2647 data
REM    137 parameters refined using      0 restraints

END

WGHT      0.0438    148.4474

REM Highest difference peak  2.802,  deepest hole -2.537,  1-sigma level  0.449
Q1    1   0.0376  0.4247  0.5792  11.00000  0.05    2.80
Q2    1   0.3498  0.4245  0.5821  11.00000  0.05    2.62
Q3    1   0.1806  0.4373  0.2469  11.00000  0.05    2.56
Q4    1   0.3210  0.5594  0.4151  11.00000  0.05    2.51
Q5    1   0.1922  0.2079  0.4949  11.00000  0.05    2.21
;
_shelx_res_checksum              48711
_olex2_submission_special_instructions 'No special instructions were received'
