# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1879162'
loop_
_audit_author_name
_audit_author_address
'Song-De Han'
;Qingdao university
China
;
_audit_update_record             
;
2018-11-15 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H21 N5 O17 P4 Zn3'
_chemical_formula_weight         875.37

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.1636(5)
_cell_length_b                   11.8340(8)
_cell_length_c                   15.8029(14)
_cell_angle_alpha                70.886(7)
_cell_angle_beta                 89.230(6)
_cell_angle_gamma                79.109(5)
_cell_volume                     1414.61(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3620
_cell_measurement_theta_min      3.3290
_cell_measurement_theta_max      30.4010

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.055
_exptl_crystal_F_000             876
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    2.837
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.541
_exptl_absorpt_correction_T_max  0.600
_exptl_absorpt_process_details   ?
_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  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7570
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.544
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_full        25.005
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4987
_reflns_number_gt                3980
_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       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0411P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4987
_refine_ls_number_parameters     412
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0937
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
O14 O -0.0550(3) 0.6704(2) 0.4388(2) 0.0181(7) Uani 1 1 d D . . . .
C1 C -0.1048(5) 0.8031(3) 0.3967(3) 0.0148(9) Uani 1 1 d . . . . .
C2 C -0.1521(5) 0.8350(4) 0.2983(3) 0.0243(10) Uani 1 1 d . . . . .
H2A H -0.060681 0.801013 0.269553 0.036 Uiso 1 1 calc R U . . .
H2B H -0.177231 0.922013 0.270695 0.036 Uiso 1 1 calc R U . . .
H2C H -0.248450 0.802121 0.292098 0.036 Uiso 1 1 calc R U . . .
C3 C 0.3455(5) 0.5142(4) 0.7335(3) 0.0182(9) Uani 1 1 d . . . . .
C4 C 0.2965(6) 0.3989(4) 0.7920(3) 0.0290(11) Uani 1 1 d . . . . .
H4A H 0.370337 0.330009 0.784098 0.043 Uiso 1 1 calc R U . . .
H4B H 0.183906 0.398315 0.775693 0.043 Uiso 1 1 calc R U . . .
H4C H 0.303993 0.394434 0.853608 0.043 Uiso 1 1 calc R U . . .
C6 C 0.3019(8) 0.2793(5) 0.2116(4) 0.0520(17) Uani 1 1 d . . . . .
H6 H 0.241042 0.356573 0.205756 0.062 Uiso 1 1 calc R U . . .
C7 C 0.3820(7) 0.2587(5) 0.1402(4) 0.0446(15) Uani 1 1 d . . . . .
H7 H 0.379221 0.321910 0.086175 0.054 Uiso 1 1 calc R U . . .
C8 C 0.4675(6) 0.1421(4) 0.1495(3) 0.0280(11) Uani 1 1 d . . . . .
C9 C 0.4660(6) 0.0510(4) 0.2297(3) 0.0305(11) Uani 1 1 d . . . . .
H9 H 0.518111 -0.028677 0.236497 0.037 Uiso 1 1 calc R U . . .
C10 C 0.3870(5) 0.0782(4) 0.2998(3) 0.0306(11) Uani 1 1 d . . . . .
H10 H 0.388049 0.017307 0.354953 0.037 Uiso 1 1 calc R U . . .
C11 C 0.5603(5) 0.1177(4) 0.0748(3) 0.0255(11) Uani 1 1 d . . . . .
C14 C 0.7180(6) 0.0279(4) 0.0010(3) 0.0273(11) Uani 1 1 d . . . . .
C16 C 0.8310(5) -0.0612(4) -0.0285(3) 0.0263(11) Uani 1 1 d . . . . .
C17 C 0.8874(6) -0.0334(5) -0.1141(4) 0.0356(13) Uani 1 1 d . . . . .
H17 H 0.854955 0.044837 -0.155033 0.043 Uiso 1 1 calc R U . . .
C18 C 0.9907(7) -0.1206(5) -0.1386(4) 0.0411(14) Uani 1 1 d . . . . .
H18 H 1.026905 -0.100662 -0.196772 0.049 Uiso 1 1 calc R U . . .
C20 C 0.9908(8) -0.2604(5) 0.0011(4) 0.0544(17) Uani 1 1 d . . . . .
H20 H 1.029220 -0.338282 0.041367 0.065 Uiso 1 1 calc R U . . .
C21 C 0.8833(7) -0.1770(5) 0.0296(4) 0.0434(14) Uani 1 1 d . . . . .
H21 H 0.846895 -0.199187 0.087755 0.052 Uiso 1 1 calc R U . . .
N1 N 0.6538(5) 0.0068(3) 0.0817(3) 0.0284(9) Uani 1 1 d . . . . .
N2 N 0.5647(5) 0.2034(4) -0.0026(3) 0.0359(11) Uani 1 1 d . . . . .
N3 N 0.6643(5) 0.1447(4) -0.0493(3) 0.0364(11) Uani 1 1 d . . . . .
H3 H 0.689992 0.177205 -0.103657 0.044 Uiso 1 1 calc R U . . .
N4 N 0.3103(5) 0.1900(4) 0.2891(3) 0.0353(10) Uani 1 1 d . . . . .
H4 H 0.263629 0.205900 0.334104 0.042 Uiso 1 1 calc R U . . .
N5 N 1.0413(6) -0.2326(4) -0.0827(3) 0.0445(12) Uani 1 1 d . . . . .
H5 H 1.105472 -0.286588 -0.099927 0.053 Uiso 1 1 calc R U . . .
O1 O 0.2238(3) 0.8001(3) 0.3729(2) 0.0204(7) Uani 1 1 d . . . . .
O2 O 0.0403(3) 0.9975(2) 0.3743(2) 0.0204(7) Uani 1 1 d . . . . .
O3 O 0.1076(3) 0.8123(2) 0.5173(2) 0.0180(6) Uani 1 1 d . . . . .
O4 O -0.2941(3) 0.9874(3) 0.4473(2) 0.0250(7) Uani 1 1 d . . . . .
O5 O -0.4348(3) 0.8310(3) 0.4258(2) 0.0221(7) Uani 1 1 d D . . . .
O6 O -0.2274(3) 0.7716(3) 0.5576(2) 0.0231(7) Uani 1 1 d . . . . .
O7 O 0.4729(4) 0.3845(3) 0.6308(2) 0.0264(7) Uani 1 1 d . . . . .
O8 O 0.4478(3) 0.6106(3) 0.5672(2) 0.0232(7) Uani 1 1 d . . . . .
O9 O 0.1887(3) 0.5170(2) 0.5812(2) 0.0199(7) Uani 1 1 d . . . . .
O10 O 0.2579(4) 0.7619(3) 0.7042(2) 0.0306(8) Uani 1 1 d . . . . .
O11 O 0.0295(3) 0.6443(3) 0.7043(2) 0.0257(7) Uani 1 1 d . . . . .
O12 O 0.1953(4) 0.6096(3) 0.8482(2) 0.0342(8) Uani 1 1 d . . . . .
O13 O -0.1780(4) 0.5116(3) 0.6153(2) 0.0311(8) Uani 1 1 d D . . . .
H13B H -0.091745 0.458573 0.607642 0.037 Uiso 1 1 d DR U . . .
H13A H -0.254282 0.528087 0.572014 0.037 Uiso 1 1 d DR U . . .
O15 O 0.5130(4) 0.5166(3) 0.7630(2) 0.0388(9) Uani 1 1 d D . . . .
H15A H 0.560827 0.479663 0.818798 0.047 Uiso 1 1 d DR U . . .
O16 O 0.7395(5) 0.2765(4) 0.7815(3) 0.0634(13) Uani 1 1 d . . . . .
O17 O 0.3939(9) 0.5487(5) 0.0545(4) 0.116(2) Uani 1 1 d . . . . .
P1 P 0.07870(12) 0.85987(9) 0.41510(8) 0.0144(2) Uani 1 1 d . . . . .
P2 P -0.27910(12) 0.85330(9) 0.46155(8) 0.0163(2) Uani 1 1 d . . . . .
P3 P 0.36364(13) 0.50737(9) 0.61932(8) 0.0151(2) Uani 1 1 d . . . . .
P4 P 0.19690(14) 0.64396(10) 0.74457(8) 0.0206(3) Uani 1 1 d . . . . .
Zn1 Zn 0.43210(5) 0.71005(4) 0.44336(3) 0.01586(13) Uani 1 1 d . . . . .
Zn2 Zn 0.15651(6) 0.89498(4) 0.59978(4) 0.01764(14) Uani 1 1 d . . . . .
Zn3 Zn -0.01787(6) 0.64012(4) 0.58292(4) 0.02019(14) Uani 1 1 d D . . . .
H14A H -0.1206(14) 0.619(2) 0.436(4) 0.07(2) Uiso 1 1 d D . . . .


_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
O14 C1 1.469(5) . ?
O14 Zn3 2.202(3) . ?
C1 C2 1.512(6) . ?
C1 P1 1.817(4) . ?
C1 P2 1.863(4) . ?
C3 O15 1.458(5) . ?
C3 C4 1.499(6) . ?
C3 P4 1.824(4) . ?
C3 P3 1.836(4) . ?
C6 N4 1.323(7) . ?
C6 C7 1.364(7) . ?
C7 C8 1.385(6) . ?
C8 C9 1.370(7) . ?
C8 C11 1.472(6) . ?
C9 C10 1.373(7) . ?
C10 N4 1.309(6) . ?
C11 N2 1.314(6) . ?
C11 N1 1.359(5) . ?
C14 N1 1.337(6) . ?
C14 N3 1.339(6) . ?
C14 C16 1.458(6) . ?
C16 C21 1.367(7) . ?
C16 C17 1.378(7) . ?
C17 C18 1.360(6) . ?
C18 N5 1.321(7) . ?
C20 N5 1.335(7) . ?
C20 C21 1.379(7) . ?
N2 N3 1.340(5) . ?
O1 P1 1.523(3) . ?
O1 Zn1 1.964(3) . ?
O2 P1 1.514(3) . ?
O2 Zn2 1.979(3) 2_576 ?
O3 P1 1.531(3) . ?
O3 Zn2 1.953(3) . ?
O3 Zn3 2.377(3) . ?
O4 P2 1.509(3) . ?
O4 Zn2 1.909(3) 2_576 ?
O5 P2 1.500(3) . ?
O5 Zn1 1.904(3) 1_455 ?
O6 P2 1.522(3) . ?
O6 Zn3 2.028(3) . ?
O7 P3 1.511(3) . ?
O7 Zn1 1.933(3) 2_666 ?
O8 P3 1.512(3) . ?
O8 Zn1 1.917(3) . ?
O9 P3 1.527(3) . ?
O9 Zn3 2.016(3) . ?
O10 P4 1.508(3) . ?
O10 Zn2 1.931(3) . ?
O11 P4 1.513(3) . ?
O11 Zn3 1.981(3) . ?
O12 P4 1.554(3) . ?
O13 Zn3 2.123(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
C1 O14 Zn3 105.3(2) . . ?
O14 C1 C2 110.4(3) . . ?
O14 C1 P1 103.7(2) . . ?
C2 C1 P1 112.7(3) . . ?
O14 C1 P2 106.2(3) . . ?
C2 C1 P2 113.4(3) . . ?
P1 C1 P2 109.8(2) . . ?
O15 C3 C4 108.6(4) . . ?
O15 C3 P4 110.0(3) . . ?
C4 C3 P4 108.8(3) . . ?
O15 C3 P3 105.7(3) . . ?
C4 C3 P3 108.1(3) . . ?
P4 C3 P3 115.5(2) . . ?
N4 C6 C7 120.3(5) . . ?
C6 C7 C8 118.9(5) . . ?
C9 C8 C7 118.8(4) . . ?
C9 C8 C11 120.9(4) . . ?
C7 C8 C11 120.3(5) . . ?
C8 C9 C10 119.5(4) . . ?
N4 C10 C9 119.9(5) . . ?
N2 C11 N1 114.8(4) . . ?
N2 C11 C8 122.3(4) . . ?
N1 C11 C8 122.8(4) . . ?
N1 C14 N3 109.8(4) . . ?
N1 C14 C16 125.7(4) . . ?
N3 C14 C16 124.5(4) . . ?
C21 C16 C17 118.1(4) . . ?
C21 C16 C14 119.7(4) . . ?
C17 C16 C14 122.2(5) . . ?
C18 C17 C16 119.8(5) . . ?
N5 C18 C17 122.3(5) . . ?
N5 C20 C21 121.9(5) . . ?
C16 C21 C20 119.2(5) . . ?
C14 N1 C11 102.2(4) . . ?
C11 N2 N3 103.1(4) . . ?
C14 N3 N2 110.1(4) . . ?
C10 N4 C6 122.4(4) . . ?
C18 N5 C20 118.6(4) . . ?
P1 O1 Zn1 120.90(18) . . ?
P1 O2 Zn2 124.66(17) . 2_576 ?
P1 O3 Zn2 130.42(17) . . ?
P1 O3 Zn3 111.11(14) . . ?
Zn2 O3 Zn3 114.74(13) . . ?
P2 O4 Zn2 135.46(18) . 2_576 ?
P2 O5 Zn1 141.8(2) . 1_455 ?
P2 O6 Zn3 119.81(17) . . ?
P3 O7 Zn1 138.4(2) . 2_666 ?
P3 O8 Zn1 132.73(19) . . ?
P3 O9 Zn3 127.09(16) . . ?
P4 O10 Zn2 125.28(19) . . ?
P4 O11 Zn3 127.07(18) . . ?
O2 P1 O1 113.00(17) . . ?
O2 P1 O3 114.33(16) . . ?
O1 P1 O3 109.66(16) . . ?
O2 P1 C1 108.16(17) . . ?
O1 P1 C1 107.49(17) . . ?
O3 P1 C1 103.54(18) . . ?
O5 P2 O4 110.19(17) . . ?
O5 P2 O6 113.45(18) . . ?
O4 P2 O6 113.69(18) . . ?
O5 P2 C1 106.54(17) . . ?
O4 P2 C1 109.47(17) . . ?
O6 P2 C1 102.97(17) . . ?
O7 P3 O8 111.57(17) . . ?
O7 P3 O9 111.74(17) . . ?
O8 P3 O9 113.56(17) . . ?
O7 P3 C3 104.62(18) . . ?
O8 P3 C3 106.61(18) . . ?
O9 P3 C3 108.14(18) . . ?
O10 P4 O11 113.58(19) . . ?
O10 P4 O12 110.37(19) . . ?
O11 P4 O12 111.55(19) . . ?
O10 P4 C3 111.83(19) . . ?
O11 P4 C3 107.80(18) . . ?
O12 P4 C3 101.00(18) . . ?
O5 Zn1 O8 109.89(13) 1_655 . ?
O5 Zn1 O7 104.51(13) 1_655 2_666 ?
O8 Zn1 O7 110.97(13) . 2_666 ?
O5 Zn1 O1 103.66(12) 1_655 . ?
O8 Zn1 O1 125.44(12) . . ?
O7 Zn1 O1 100.26(12) 2_666 . ?
O4 Zn2 O10 113.25(14) 2_576 . ?
O4 Zn2 O3 114.15(13) 2_576 . ?
O10 Zn2 O3 103.08(12) . . ?
O4 Zn2 O2 99.00(11) 2_576 2_576 ?
O10 Zn2 O2 113.69(13) . 2_576 ?
O3 Zn2 O2 114.21(12) . 2_576 ?
O11 Zn3 O9 96.23(12) . . ?
O11 Zn3 O6 94.73(12) . . ?
O9 Zn3 O6 168.49(13) . . ?
O11 Zn3 O13 99.61(13) . . ?
O9 Zn3 O13 94.62(11) . . ?
O6 Zn3 O13 86.98(12) . . ?
O11 Zn3 O14 168.71(12) . . ?
O9 Zn3 O14 86.69(11) . . ?
O6 Zn3 O14 81.89(11) . . ?
O13 Zn3 O14 91.00(12) . . ?
O11 Zn3 O3 90.61(11) . . ?
O9 Zn3 O3 94.70(10) . . ?
O6 Zn3 O3 81.68(11) . . ?
O13 Zn3 O3 165.33(11) . . ?
O14 Zn3 O3 78.26(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4A O7 0.96 2.47 2.946(6) 110.3 .
C6 H6 O11 0.93 2.61 3.109(6) 114.2 2_566
C7 H7 O17 0.93 2.59 3.270(8) 130.5 .
C10 H10 O5 0.93 2.33 3.049(6) 133.8 1_645
C17 H17 O16 0.93 2.58 3.470(6) 160.4 1_554
N3 H3 O16 0.86 1.90 2.747(6) 169.3 1_554
N4 H4 O6 0.86 1.83 2.664(5) 163.3 2_566
N4 H4 O11 0.86 2.64 3.102(5) 114.9 2_566
N5 H5 O12 0.86 1.74 2.582(5) 166.5 1_644
O13 H13B O9 0.89 2.51 3.043(4) 119.7 .
O13 H13B O14 0.89 2.08 2.932(4) 161.5 2_566
O13 H13A O8 0.88 2.44 3.067(4) 129.2 1_455
O15 H15A O17 0.90 1.95 2.805(7) 158.4 2_666
O14 H14A O9 0.897(10) 1.895(13) 2.756(4) 160(2) 2_566
C4 H4A O7 0.96 2.47 2.946(6) 110.3 .
C6 H6 O11 0.93 2.61 3.109(6) 114.2 2_566
C7 H7 O17 0.93 2.59 3.270(8) 130.5 .
C10 H10 O5 0.93 2.33 3.049(6) 133.8 1_645
C17 H17 O16 0.93 2.58 3.470(6) 160.4 1_554
N3 H3 O16 0.86 1.90 2.747(6) 169.3 1_554
N4 H4 O6 0.86 1.83 2.664(5) 163.3 2_566
N4 H4 O11 0.86 2.64 3.102(5) 114.9 2_566
N5 H5 O12 0.86 1.74 2.582(5) 166.5 1_644
O13 H13B O14 0.89 2.08 2.932(4) 161.5 2_566
O13 H13B O9 0.89 2.51 3.043(4) 119.7 .
O13 H13A O8 0.88 2.44 3.067(4) 129.2 1_455
O15 H15A O17 0.90 1.95 2.805(7) 158.4 2_666
O14 H14A O9 0.897(10) 1.895(13) 2.756(4) 160(2) 2_566

_refine_diff_density_max         1.074
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.107

####################################################################### 
# 
# 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_2_sq
_database_code_depnum_ccdc_archive 'CCDC 1879163'
loop_
_audit_author_name
_audit_author_address
'Song-De Han'
;Qingdao university
China
;
_audit_update_record             
;
2018-11-15 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H14 N O9 P2 Zn2'
_chemical_formula_weight         484.90

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   5.4607(3)
_cell_length_b                   8.5135(5)
_cell_length_c                   18.0158(11)
_cell_angle_alpha                87.6780(10)
_cell_angle_beta                 82.1720(10)
_cell_angle_gamma                81.0300(10)
_cell_volume                     819.44(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9943
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.965
_exptl_crystal_F_000             486
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    3.167
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.503
_exptl_absorpt_correction_T_max  0.565
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16267
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.283
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3715
_reflns_number_gt                3294
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.16b (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0314P)²+0.5388P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3715
_refine_ls_number_parameters     209
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0212
_refine_ls_wR_factor_ref         0.0581
_refine_ls_wR_factor_gt          0.0559
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.004
_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
O6 O -0.2284(3) 0.93277(16) 0.83667(8) 0.0159(3) Uani 1 1 d . . . . .
C3 C 0.2213(4) -0.0338(3) 0.69075(12) 0.0166(4) Uani 1 1 d . . . . .
H3 H 0.095626 -0.100603 0.696104 0.020 Uiso 1 1 calc R U . . .
C4 C 0.4043(4) -0.0528(3) 0.62952(12) 0.0192(5) Uani 1 1 d . . . . .
H4 H 0.402592 -0.130871 0.593436 0.023 Uiso 1 1 calc R U . . .
C5 C 0.5908(4) 0.0426(3) 0.62092(12) 0.0184(4) Uani 1 1 d . . . . .
C6 C 0.5814(4) 0.1559(3) 0.67494(13) 0.0233(5) Uani 1 1 d . . . . .
H6 H 0.704722 0.224217 0.670868 0.028 Uiso 1 1 calc R U . . .
C7 C 0.3919(4) 0.1689(3) 0.73469(13) 0.0213(5) Uani 1 1 d . . . . .
H7 H 0.387792 0.247008 0.771203 0.026 Uiso 1 1 calc R U . . .
C8 C 0.7990(4) 0.0215(3) 0.55801(12) 0.0210(5) Uani 1 1 d . . . . .
C1 C -0.2228(4) 0.6180(2) 0.82424(11) 0.0103(4) Uani 1 1 d . . . . .
C2 C -0.3665(4) 0.6624(2) 0.75778(12) 0.0170(4) Uani 1 1 d . . . . .
H2A H -0.301084 0.750952 0.729404 0.025 Uiso 1 1 calc R U . . .
H2B H -0.544184 0.694273 0.775909 0.025 Uiso 1 1 calc R U . . .
H2C H -0.346749 0.570528 0.725244 0.025 Uiso 1 1 calc R U . . .
C10 C 0.9116(5) 0.1495(3) 0.52836(13) 0.0272(5) Uani 1 1 d . . . . .
H10 H 0.851967 0.252735 0.547547 0.033 Uiso 1 1 calc R U . . .
C9 C 0.8896(4) -0.1287(3) 0.52897(13) 0.0257(5) Uani 1 1 d . . . . .
H9 H 0.814697 -0.217710 0.548602 0.031 Uiso 1 1 calc R U . . .
N1 N 0.2140(3) 0.0752(2) 0.74295(9) 0.0138(3) Uani 1 1 d . . . . .
O1 O 0.1751(3) 0.09593(17) 0.91379(8) 0.0185(3) Uani 1 1 d D . . . .
H1A H 0.163412 0.148279 0.946326 0.022 Uiso 1 1 d DR U . . .
H1B H 0.272769 0.005120 0.918679 0.022 Uiso 1 1 d DR U . . .
O2 O -0.2421(3) 0.30493(16) 0.81748(8) 0.0140(3) Uani 1 1 d . . . . .
O8 O -0.5420(2) 0.80982(15) 0.92511(8) 0.0117(3) Uani 1 1 d . . . . .
O3 O -0.1931(3) 0.41313(17) 0.94121(8) 0.0154(3) Uani 1 1 d . . . . .
O7 O -0.0896(2) 0.75911(16) 0.94485(8) 0.0128(3) Uani 1 1 d . . . . .
O4 O -0.6091(3) 0.47589(16) 0.88928(8) 0.0126(3) Uani 1 1 d . . . . .
O5 O 0.0387(3) 0.58677(17) 0.79349(8) 0.0168(3) Uani 1 1 d D . . . .
H5B H 0.127505 0.532885 0.827117 0.020 Uiso 1 1 d DR U . . .
P1 P -0.32424(9) 0.44046(5) 0.87209(3) 0.00875(10) Uani 1 1 d . . . . .
P2 P -0.27074(9) 0.79008(5) 0.88709(3) 0.00851(10) Uani 1 1 d . . . . .
Zn1 Zn -0.04458(4) 0.10490(2) 0.83564(2) 0.01047(7) Uani 1 1 d . . . . .
Zn2 Zn -0.23939(4) 0.35161(2) 1.04411(2) 0.00997(7) Uani 1 1 d . . . . .


_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
O6 P2 1.5151(14) . ?
O6 Zn1 1.8990(14) 1_565 ?
C3 N1 1.340(3) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(3) . ?
C5 C8 1.487(3) . ?
C6 C7 1.383(3) . ?
C6 H6 0.9500 . ?
C7 N1 1.339(3) . ?
C7 H7 0.9500 . ?
C8 C10 1.387(3) . ?
C8 C9 1.393(3) . ?
C1 O5 1.447(2) . ?
C1 C2 1.523(3) . ?
C1 P1 1.8329(19) . ?
C1 P2 1.852(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C10 C9 1.388(3) 2_756 ?
C10 H10 0.9500 . ?
C9 H9 0.9500 . ?
N1 Zn1 2.0315(17) . ?
O1 Zn1 1.9621(15) . ?
O1 H1A 0.7405 . ?
O1 H1B 0.8768 . ?
O2 P1 1.5202(14) . ?
O2 Zn1 1.9102(13) . ?
O8 P2 1.5319(14) . ?
O8 Zn2 1.9725(13) 2_467 ?
O3 P1 1.5114(15) . ?
O3 Zn2 1.9000(14) . ?
O7 P2 1.5192(14) . ?
O7 Zn2 1.9260(13) 2_567 ?
O4 P1 1.5285(14) . ?
O4 Zn2 1.9429(14) 2_467 ?
O5 H5B 0.8950 . ?

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
P2 O6 Zn1 136.66(9) . 1_565 ?
N1 C3 C4 122.5(2) . . ?
N1 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 117.49(19) . . ?
C4 C5 C8 121.7(2) . . ?
C6 C5 C8 120.7(2) . . ?
C5 C6 C7 119.7(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
N1 C7 C6 122.4(2) . . ?
N1 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C10 C8 C9 118.6(2) . . ?
C10 C8 C5 121.0(2) . . ?
C9 C8 C5 120.5(2) . . ?
O5 C1 C2 106.07(16) . . ?
O5 C1 P1 110.90(12) . . ?
C2 C1 P1 109.51(13) . . ?
O5 C1 P2 108.67(13) . . ?
C2 C1 P2 109.11(13) . . ?
P1 C1 P2 112.37(10) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C9 C10 C8 120.8(2) 2_756 . ?
C9 C10 H10 119.6 2_756 . ?
C8 C10 H10 119.6 . . ?
C10 C9 C8 120.6(2) 2_756 . ?
C10 C9 H9 119.7 2_756 . ?
C8 C9 H9 119.7 . . ?
C7 N1 C3 118.16(18) . . ?
C7 N1 Zn1 117.44(14) . . ?
C3 N1 Zn1 124.38(14) . . ?
Zn1 O1 H1A 128.6 . . ?
Zn1 O1 H1B 115.6 . . ?
H1A O1 H1B 113.3 . . ?
P1 O2 Zn1 126.85(9) . . ?
P2 O8 Zn2 130.08(8) . 2_467 ?
P1 O3 Zn2 143.02(10) . . ?
P2 O7 Zn2 140.35(9) . 2_567 ?
P1 O4 Zn2 119.24(8) . 2_467 ?
C1 O5 H5B 109.9 . . ?
O3 P1 O2 111.70(8) . . ?
O3 P1 O4 113.72(8) . . ?
O2 P1 O4 111.41(8) . . ?
O3 P1 C1 106.48(9) . . ?
O2 P1 C1 106.43(8) . . ?
O4 P1 C1 106.56(8) . . ?
O7 P2 O6 112.68(8) . . ?
O7 P2 O8 110.84(8) . . ?
O6 P2 O8 110.24(8) . . ?
O7 P2 C1 109.41(8) . . ?
O6 P2 C1 105.79(9) . . ?
O8 P2 C1 107.63(8) . . ?
O6 Zn1 O2 112.30(6) 1_545 . ?
O6 Zn1 O1 115.45(6) 1_545 . ?
O2 Zn1 O1 117.24(6) . . ?
O6 Zn1 N1 105.48(7) 1_545 . ?
O2 Zn1 N1 103.70(6) . . ?
O1 Zn1 N1 100.31(7) . . ?
O3 Zn2 O7 100.56(6) . 2_567 ?
O3 Zn2 O4 114.13(6) . 2_467 ?
O7 Zn2 O4 119.84(6) 2_567 2_467 ?
O3 Zn2 O8 118.10(6) . 2_467 ?
O7 Zn2 O8 103.35(6) 2_567 2_467 ?
O4 Zn2 O8 101.32(6) 2_467 2_467 ?

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
N1 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C3 C4 C5 C8 177.0(2) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C8 C5 C6 C7 -177.3(2) . . . . ?
C5 C6 C7 N1 0.1(4) . . . . ?
C4 C5 C8 C10 149.8(2) . . . . ?
C6 C5 C8 C10 -32.5(3) . . . . ?
C4 C5 C8 C9 -32.0(3) . . . . ?
C6 C5 C8 C9 145.7(2) . . . . ?
C9 C8 C10 C9 0.0(4) . . . 2_756 ?
C5 C8 C10 C9 178.2(2) . . . 2_756 ?
C10 C8 C9 C10 0.0(4) . . . 2_756 ?
C5 C8 C9 C10 -178.2(2) . . . 2_756 ?
C6 C7 N1 C3 -0.4(3) . . . . ?
C6 C7 N1 Zn1 178.08(18) . . . . ?
C4 C3 N1 C7 0.1(3) . . . . ?
C4 C3 N1 Zn1 -178.26(16) . . . . ?
Zn2 O3 P1 O2 -103.98(16) . . . . ?
Zn2 O3 P1 O4 23.19(18) . . . . ?
Zn2 O3 P1 C1 140.23(15) . . . . ?
Zn1 O2 P1 O3 10.18(14) . . . . ?
Zn1 O2 P1 O4 -118.22(11) . . . . ?
Zn1 O2 P1 C1 126.01(11) . . . . ?
Zn2 O4 P1 O3 54.25(11) 2_467 . . . ?
Zn2 O4 P1 O2 -178.44(8) 2_467 . . . ?
Zn2 O4 P1 C1 -62.75(11) 2_467 . . . ?
O5 C1 P1 O3 68.63(15) . . . . ?
C2 C1 P1 O3 -174.65(13) . . . . ?
P2 C1 P1 O3 -53.23(12) . . . . ?
O5 C1 P1 O2 -50.66(15) . . . . ?
C2 C1 P1 O2 66.06(15) . . . . ?
P2 C1 P1 O2 -172.51(9) . . . . ?
O5 C1 P1 O4 -169.66(12) . . . . ?
C2 C1 P1 O4 -52.94(15) . . . . ?
P2 C1 P1 O4 68.49(12) . . . . ?
Zn2 O7 P2 O6 -86.96(15) 2_567 . . . ?
Zn2 O7 P2 O8 148.97(12) 2_567 . . . ?
Zn2 O7 P2 C1 30.43(16) 2_567 . . . ?
Zn1 O6 P2 O7 -12.62(17) 1_565 . . . ?
Zn1 O6 P2 O8 111.78(13) 1_565 . . . ?
Zn1 O6 P2 C1 -132.12(13) 1_565 . . . ?
Zn2 O8 P2 O7 -86.69(12) 2_467 . . . ?
Zn2 O8 P2 O6 147.85(10) 2_467 . . . ?
Zn2 O8 P2 C1 32.91(14) 2_467 . . . ?
O5 C1 P2 O7 -53.71(14) . . . . ?
C2 C1 P2 O7 -168.95(13) . . . . ?
P1 C1 P2 O7 69.40(12) . . . . ?
O5 C1 P2 O6 67.92(14) . . . . ?
C2 C1 P2 O6 -47.31(15) . . . . ?
P1 C1 P2 O6 -168.96(10) . . . . ?
O5 C1 P2 O8 -174.22(12) . . . . ?
C2 C1 P2 O8 70.54(15) . . . . ?
P1 C1 P2 O8 -51.11(12) . . . . ?

_refine_diff_density_max         0.533
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.073



