# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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 1891504'
loop_
_audit_author_name
_audit_author_address
'Qi Wei'
;Qingdao University
China
;
_audit_update_record             
;
2019-01-17 deposited with the CCDC.	2019-03-05 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            'C34 H36 N5 O13 P3 Zn3'
_chemical_formula_weight         1011.70

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      orthorhombic
_space_group_IT_number           70
_space_group_name_H-M_alt        'F d d d'
_space_group_name_Hall           '-F 2uv 2vw'

_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+3/4, -y+3/4, z'
'-x+3/4, y, -z+3/4'
'x, -y+3/4, -z+3/4'
'x, y+1/2, z+1/2'
'-x+3/4, -y+5/4, z+1/2'
'-x+3/4, y+1/2, -z+5/4'
'x, -y+5/4, -z+5/4'
'x+1/2, y, z+1/2'
'-x+5/4, -y+3/4, z+1/2'
'-x+5/4, y, -z+5/4'
'x+1/2, -y+3/4, -z+5/4'
'x+1/2, y+1/2, z'
'-x+5/4, -y+5/4, z'
'-x+5/4, y+1/2, -z+3/4'
'x+1/2, -y+5/4, -z+3/4'
'-x, -y, -z'
'x-3/4, y-3/4, -z'
'x-3/4, -y, z-3/4'
'-x, y-3/4, z-3/4'
'-x, -y+1/2, -z+1/2'
'x-3/4, y-1/4, -z+1/2'
'x-3/4, -y+1/2, z-1/4'
'-x, y-1/4, z-1/4'
'-x+1/2, -y, -z+1/2'
'x-1/4, y-3/4, -z+1/2'
'x-1/4, -y, z-1/4'
'-x+1/2, y-3/4, z-1/4'
'-x+1/2, -y+1/2, -z'
'x-1/4, y-1/4, -z'
'x-1/4, -y+1/2, z-3/4'
'-x+1/2, y-1/4, z-3/4'

_cell_length_a                   20.7520(10)
_cell_length_b                   24.4248(14)
_cell_length_c                   29.3054(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     14853.8(14)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3989
_cell_measurement_theta_min      2.7720
_cell_measurement_theta_max      30.0670

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.810
_exptl_crystal_F_000             8224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.32
_exptl_absorpt_coefficient_mu    2.127
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.255
_exptl_absorpt_correction_T_max  0.506
_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            7906
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.576
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_full        25.007
_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             3283
_reflns_number_gt                2458
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.1156P)²+49.8921P] 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         3283
_refine_ls_number_parameters     266
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1517
_refine_ls_wR_factor_gt          0.1356
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_restrained_S_all      1.019
_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
C1 C 0.4681(3) 0.4763(3) 0.7007(2) 0.0408(16) Uani 1 1 d . . . . .
H1 H 0.447765 0.454478 0.679093 0.049 Uiso 1 1 calc R U . . .
C2 C 0.5322(3) 0.4886(3) 0.6947(2) 0.0475(18) Uani 1 1 d . . . . .
H2 H 0.554251 0.475158 0.669461 0.057 Uiso 1 1 calc R U . . .
C3 C 0.5639(3) 0.5210(3) 0.7261(3) 0.0474(17) Uani 1 1 d . . . . .
C4 C 0.5290(3) 0.5381(3) 0.7636(2) 0.0365(15) Uani 1 1 d . . . . .
H4 H 0.548755 0.558875 0.786269 0.044 Uiso 1 1 calc R U . . .
C5 C 0.4649(3) 0.5244(3) 0.7674(2) 0.0351(14) Uani 1 1 d . . . . .
H5 H 0.442047 0.536523 0.792776 0.042 Uiso 1 1 calc R U . . .
C6 C 0.6323(3) 0.5372(4) 0.7195(3) 0.062(2) Uani 1 1 d . . . . .
C7 C 0.6562(6) 0.5496(7) 0.6750(5) 0.053(3) Uani 0.520(8) 1 d . U P A 1
H7 H 0.628617 0.549451 0.649999 0.064 Uiso 0.520(8) 1 calc R U P A 1
C7A C 0.6700(7) 0.4998(7) 0.6869(5) 0.053(3) Uani 0.480(8) 1 d . U P A 2
H7A H 0.650926 0.469959 0.672505 0.064 Uiso 0.480(8) 1 calc R U P A 2
C8 C 0.7191(6) 0.5617(6) 0.6696(5) 0.052(3) Uani 0.520(8) 1 d . U P A 1
H8 H 0.733856 0.569169 0.640303 0.063 Uiso 0.520(8) 1 calc R U P A 1
C8A C 0.7344(7) 0.5133(7) 0.6801(5) 0.052(3) Uani 0.480(8) 1 d . U P A 2
H8A H 0.760154 0.492123 0.661074 0.063 Uiso 0.480(8) 1 calc R U P A 2
C9 C 0.7625(3) 0.5635(4) 0.7045(3) 0.066(2) Uani 1 1 d . . . . .
C10 C 0.7334(4) 0.5726(3) 0.7456(3) 0.067(3) Uani 1 1 d . . . . .
H10 H 0.757110 0.587445 0.769507 0.080 Uiso 1 1 calc R U . . .
C11 C 0.6695(4) 0.5600(4) 0.7520(3) 0.076(3) Uani 1 1 d . . . . .
H11 H 0.650959 0.567700 0.780172 0.092 Uiso 1 1 calc R U . . .
C12 C 0.8315(3) 0.5738(3) 0.6960(2) 0.0467(17) Uani 1 1 d . . . . .
C13 C 0.8629(3) 0.5518(3) 0.6589(3) 0.054(2) Uani 1 1 d . . . . .
H13 H 0.839553 0.531693 0.637632 0.064 Uiso 1 1 calc R U . . .
C14 C 0.9281(3) 0.5590(3) 0.6528(2) 0.0477(18) Uani 1 1 d . . . . .
H14 H 0.948638 0.543808 0.627579 0.057 Uiso 1 1 calc R U . . .
C15 C 0.9337(3) 0.6106(3) 0.7192(2) 0.0429(16) Uani 1 1 d . . . . .
H15 H 0.958228 0.631051 0.739625 0.052 Uiso 1 1 calc R U . . .
C16 C 0.8688(3) 0.6041(3) 0.7264(3) 0.0508(19) Uani 1 1 d . . . . .
H16 H 0.849610 0.620009 0.751760 0.061 Uiso 1 1 calc R U . . .
N1 N 0.4339(2) 0.49425(19) 0.73598(16) 0.0278(11) Uani 1 1 d . . . . .
N2 N 0.9614(2) 0.5878(2) 0.68305(18) 0.0328(11) Uani 1 1 d . . . . .
O1 O 0.20209(18) 0.51817(15) 0.81599(12) 0.0292(9) Uani 1 1 d D . . . .
O2 O 0.31240(19) 0.53600(15) 0.78266(12) 0.0289(9) Uani 1 1 d D . . . .
O3 O 0.26779(19) 0.59759(15) 0.84110(14) 0.0366(10) Uani 1 1 d D . . . .
H3 H 0.224627 0.604878 0.852440 0.055 Uiso 1 1 d DR U . . .
O4 O 0.29825(18) 0.50226(17) 0.86376(12) 0.0302(9) Uani 1 1 d . . . . .
O5 O 0.41169(16) 0.41589(14) 0.82637(11) 0.0192(7) Uani 1 1 d . . . . .
O6 O 0.32485(17) 0.40467(15) 0.76747(13) 0.0267(9) Uani 1 1 d . . . . .
C17 C 0.1805(2) 0.6214(3) 0.89761(18) 0.0360(16) Uani 1 1 d D . . . .
P1 P 0.375000 0.375000 0.79620(6) 0.0157(4) Uani 1 2 d S T P . .
P2 P 0.27057(6) 0.53600(5) 0.82526(4) 0.0199(3) Uani 1 1 d D . . . .
Zn1 Zn 0.33755(3) 0.47694(2) 0.74335(2) 0.0200(2) Uani 1 1 d . . . . .
Zn2 Zn 0.375000 0.46096(3) 0.875000 0.0165(2) Uani 1 2 d S T P . .
N3 N 0.125000 0.625000 0.8773(3) 0.100(5) Uani 1 2 d DS T P . .


_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 1.327(8) . ?
C1 C2 1.376(9) . ?
C2 C3 1.378(10) . ?
C3 C4 1.382(10) . ?
C3 C6 1.486(9) . ?
C4 C5 1.376(8) . ?
C5 N1 1.343(8) . ?
C6 C11 1.346(11) . ?
C6 C7 1.429(17) . ?
C6 C7A 1.538(18) . ?
C7 C8 1.348(18) . ?
C7A C8A 1.39(2) . ?
C8 C9 1.363(16) . ?
C8A C9 1.535(17) . ?
C9 C10 1.364(11) . ?
C9 C12 1.476(9) . ?
C10 C11 1.375(10) . ?
C12 C16 1.391(9) . ?
C12 C13 1.377(9) . ?
C13 C14 1.377(9) . ?
C14 N2 1.326(8) . ?
C15 N2 1.329(8) . ?
C15 C16 1.372(9) . ?
N1 Zn1 2.056(5) . ?
O1 P2 1.511(4) . ?
O1 Zn1 1.927(4) 25_566 ?
O2 P2 1.521(4) . ?
O2 Zn1 1.918(4) . ?
O3 P2 1.575(4) . ?
O4 P2 1.510(4) . ?
O4 Zn2 1.914(4) . ?
O5 P1 1.536(3) . ?
O5 Zn2 1.955(3) . ?
O6 P1 1.522(4) . ?
O6 Zn1 1.920(4) . ?
C17 N3 1.299(6) . ?

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 C2 123.0(6) . . ?
C1 C2 C3 120.0(6) . . ?
C4 C3 C2 117.1(6) . . ?
C4 C3 C6 121.5(7) . . ?
C2 C3 C6 121.4(7) . . ?
C5 C4 C3 119.8(6) . . ?
N1 C5 C4 122.7(6) . . ?
C11 C6 C7 110.9(9) . . ?
C11 C6 C3 124.6(7) . . ?
C7 C6 C3 120.4(8) . . ?
C11 C6 C7A 113.2(8) . . ?
C3 C6 C7A 114.1(8) . . ?
C8 C7 C6 119.4(13) . . ?
C8A C7A C6 115.9(13) . . ?
C7 C8 C9 124.0(13) . . ?
C7A C8A C9 119.2(13) . . ?
C8 C9 C10 112.1(8) . . ?
C8 C9 C12 121.3(9) . . ?
C10 C9 C12 123.4(7) . . ?
C10 C9 C8A 111.9(8) . . ?
C12 C9 C8A 115.2(8) . . ?
C11 C10 C9 120.7(7) . . ?
C6 C11 C10 123.4(8) . . ?
C16 C12 C13 116.7(6) . . ?
C16 C12 C9 121.6(6) . . ?
C13 C12 C9 121.7(6) . . ?
C14 C13 C12 121.2(6) . . ?
N2 C14 C13 119.5(6) . . ?
N2 C15 C16 119.8(6) . . ?
C15 C16 C12 120.7(6) . . ?
C1 N1 C5 117.3(5) . . ?
C1 N1 Zn1 122.2(4) . . ?
C5 N1 Zn1 120.4(4) . . ?
C15 N2 C14 122.1(5) . . ?
P2 O1 Zn1 123.1(2) . 25_566 ?
P2 O2 Zn1 130.4(2) . . ?
P2 O4 Zn2 137.1(2) . . ?
P1 O5 Zn2 126.3(2) . . ?
P1 O6 Zn1 123.2(2) . . ?
O6 P1 O6 112.8(3) 2 . ?
O6 P1 O5 106.80(18) 2 . ?
O6 P1 O5 110.35(19) . . ?
O6 P1 O5 110.35(19) 2 2 ?
O6 P1 O5 106.80(18) . 2 ?
O5 P1 O5 109.7(3) . 2 ?
O1 P2 O4 109.6(2) . . ?
O1 P2 O2 112.9(2) . . ?
O4 P2 O2 113.3(2) . . ?
O1 P2 O3 107.1(2) . . ?
O4 P2 O3 108.3(2) . . ?
O2 P2 O3 105.2(2) . . ?
O2 Zn1 O6 115.66(16) . . ?
O2 Zn1 O1 112.28(16) . 25_566 ?
O6 Zn1 O1 109.30(16) . 25_566 ?
O2 Zn1 N1 99.97(18) . . ?
O6 Zn1 N1 111.18(17) . . ?
O1 Zn1 N1 107.92(17) 25_566 . ?
O4 Zn2 O4 116.4(3) . 3_556 ?
O4 Zn2 O5 119.69(15) . . ?
O4 Zn2 O5 95.64(14) 3_556 . ?
O4 Zn2 O5 95.63(14) . 3_556 ?
O4 Zn2 O5 119.69(15) 3_556 3_556 ?
O5 Zn2 O5 111.5(2) . 3_556 ?
C17 N3 C17 125.4(9) . 14_455 ?

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
O3 H3 N3 0.97 2.25 3.218(5) 177.7 .
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
O3 H3 N3 0.97 2.25 3.218(5) 177.7 .
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
O3 H3 N3 0.97 2.25 3.218(5) 177.7 .
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
O3 H3 N3 0.97 2.25 3.218(5) 177.7 .
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C1 H1 N3 0.93 2.96 3.884(9) 170.9 25_566
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C1 H1 N3 0.93 2.96 3.884(9) 170.9 25_566
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C1 H1 N3 0.93 2.96 3.884(9) 170.9 25_566
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C1 H1 N3 0.93 2.96 3.884(9) 170.9 25_566
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C1 H1 N3 0.93 2.96 3.884(9) 170.9 25_566
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C1 H1 N3 0.93 2.96 3.884(9) 170.9 25_566
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
O3 H3 N3 0.97 2.25 3.218(5) 177.7 .
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
O3 H3 N3 0.97 2.25 3.218(5) 177.7 .
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
O3 H3 N3 0.97 2.25 3.218(5) 177.7 .
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
O3 H3 N3 0.97 2.25 3.218(5) 177.7 .
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
O3 H3 N3 0.97 2.25 3.218(5) 177.7 .
C14 H14 O1 0.93 2.36 3.205(7) 151.5 27_665
C14 H14 O4 0.93 2.39 3.125(8) 136.0 27_665
C15 H15 O2 0.93 2.42 3.136(7) 133.3 14
C15 H15 O6 0.93 2.50 3.144(7) 126.9 26_666
O3 H3 N3 0.97 2.25 3.218(5) 177.7 .

_refine_diff_density_max         2.026
_refine_diff_density_min         -0.790
_refine_diff_density_rms         0.123



####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1891505'
loop_
_audit_author_name
_audit_author_address
'Qi Wei'
;Qingdao University
China
;
_audit_update_record             
;
2019-01-17 deposited with the CCDC.	2019-03-05 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            'C8 H13 N O7 P Zn'
_chemical_formula_weight         331.53

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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   26.027(2)
_cell_length_b                   10.6307(9)
_cell_length_c                   9.0300(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.901(8)
_cell_angle_gamma                90
_cell_volume                     2485.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2184
_cell_measurement_theta_min      3.0090
_cell_measurement_theta_max      31.3470

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_F_000             1352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    2.130
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.671
_exptl_absorpt_correction_T_max  0.791
_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            3976
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.011
_diffrn_reflns_theta_max         24.976
_diffrn_reflns_theta_full        24.976
_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             2195
_reflns_number_gt                1894
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0208P)²+8.0055P] 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         2195
_refine_ls_number_parameters     145
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0717
_refine_ls_wR_factor_gt          0.0696
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
C1 C 0.13915(13) 0.1692(3) 0.8911(4) 0.0349(8) Uani 1 1 d . . . . .
H1 H 0.147629 0.249608 0.926142 0.042 Uiso 1 1 calc R U . . .
C2 C 0.09825(13) 0.1556(3) 0.7834(4) 0.0388(8) Uani 1 1 d . . . . .
H2 H 0.079632 0.225913 0.747818 0.047 Uiso 1 1 calc R U . . .
C3 C 0.08465(12) 0.0375(3) 0.7278(3) 0.0267(7) Uani 1 1 d . . . . .
C4 C 0.11416(13) -0.0619(3) 0.7876(4) 0.0335(8) Uani 1 1 d . . . . .
H4 H 0.106849 -0.143278 0.754084 0.040 Uiso 1 1 calc R U . . .
C5 C 0.15394(13) -0.0413(3) 0.8956(3) 0.0314(7) Uani 1 1 d . . . . .
H5 H 0.172787 -0.110060 0.934876 0.038 Uiso 1 1 calc R U . . .
C6 C 0.04151(12) 0.0186(3) 0.6106(3) 0.0278(7) Uani 1 1 d . . . . .
C7 C 0.01907(14) 0.1186(3) 0.5296(4) 0.0380(8) Uani 1 1 d . . . . .
H7 H 0.031544 0.199553 0.548762 0.046 Uiso 1 1 calc R U . . .
C8 C 0.02143(13) -0.1000(3) 0.5789(4) 0.0361(8) Uani 1 1 d . . . . .
H8 H 0.035590 -0.168765 0.632118 0.043 Uiso 1 1 calc R U . . .
N1 N 0.16700(9) 0.0733(2) 0.9473(3) 0.0244(5) Uani 1 1 d . . . . .
O1 O 0.28600(8) 0.09821(19) 0.9301(2) 0.0283(5) Uani 1 1 d . . . . .
O2 O 0.33180(8) 0.1588(2) 0.7197(2) 0.0352(5) Uani 1 1 d D . . . .
H2A H 0.329272 0.157104 0.625711 0.053 Uiso 1 1 d DR U . . .
O3 O 0.25499(9) 0.28650(19) 0.7789(2) 0.0335(5) Uani 1 1 d . . . . .
O4 O 0.24112(8) 0.07784(18) 0.6673(2) 0.0274(5) Uani 1 1 d D . . . .
P1 P 0.27659(3) 0.15429(7) 0.77457(8) 0.02128(18) Uani 1 1 d . . . . .
Zn1 Zn 0.23534(2) 0.08369(3) 1.07546(3) 0.02073(12) Uani 1 1 d . . . . .
O5 O 0.33160(10) 0.1422(2) 0.4275(3) 0.0450(6) 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
C1 N1 1.322(4) . ?
C1 C2 1.374(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.384(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(4) . ?
C3 C6 1.475(4) . ?
C4 C5 1.365(4) . ?
C4 H4 0.9300 . ?
C5 N1 1.336(4) . ?
C5 H5 0.9300 . ?
C6 C8 1.383(4) . ?
C6 C7 1.385(4) . ?
C7 C8 1.378(4) 5_556 ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
N1 Zn1 2.023(2) . ?
O1 P1 1.523(2) . ?
O1 Zn1 1.960(2) . ?
O2 P1 1.568(2) . ?
O2 H2A 0.8443 . ?
O3 P1 1.516(2) . ?
O3 Zn1 1.905(2) 7_557 ?
O4 P1 1.506(2) . ?
O4 Zn1 1.9061(19) 6 ?

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 C2 123.0(3) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 116.1(3) . . ?
C2 C3 C6 122.1(3) . . ?
C4 C3 C6 121.8(3) . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
N1 C5 C4 122.9(3) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C8 C6 C7 117.4(3) . . ?
C8 C6 C3 121.1(3) . . ?
C7 C6 C3 121.5(3) . . ?
C8 C7 C6 121.1(3) 5_556 . ?
C8 C7 H7 119.5 5_556 . ?
C6 C7 H7 119.5 . . ?
C7 C8 C6 121.5(3) 5_556 . ?
C7 C8 H8 119.2 5_556 . ?
C6 C8 H8 119.2 . . ?
C1 N1 C5 117.4(3) . . ?
C1 N1 Zn1 126.3(2) . . ?
C5 N1 Zn1 115.28(19) . . ?
P1 O1 Zn1 126.38(13) . . ?
P1 O2 H2A 109.7 . . ?
P1 O3 Zn1 131.80(13) . 7_557 ?
P1 O4 Zn1 141.44(14) . 6 ?
O4 P1 O3 108.22(12) . . ?
O4 P1 O1 114.33(12) . . ?
O3 P1 O1 111.35(12) . . ?
O4 P1 O2 109.52(12) . . ?
O3 P1 O2 109.54(13) . . ?
O1 P1 O2 103.76(12) . . ?
O3 Zn1 O4 110.69(9) 7_557 6_556 ?
O3 Zn1 O1 110.79(10) 7_557 . ?
O4 Zn1 O1 109.51(9) 6_556 . ?
O3 Zn1 N1 118.73(10) 7_557 . ?
O4 Zn1 N1 103.01(9) 6_556 . ?
O1 Zn1 N1 103.52(9) . . ?

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 C1 C2 C3 -0.4(6) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C1 C2 C3 C6 -179.1(3) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C6 C3 C4 C5 179.8(3) . . . . ?
C3 C4 C5 N1 -1.0(5) . . . . ?
C2 C3 C6 C8 -166.0(3) . . . . ?
C4 C3 C6 C8 14.5(5) . . . . ?
C2 C3 C6 C7 13.1(5) . . . . ?
C4 C3 C6 C7 -166.4(3) . . . . ?
C8 C6 C7 C8 -0.4(6) . . . 5_556 ?
C3 C6 C7 C8 -179.6(3) . . . 5_556 ?
C7 C6 C8 C7 0.5(6) . . . 5_556 ?
C3 C6 C8 C7 179.6(3) . . . 5_556 ?
C2 C1 N1 C5 -0.2(5) . . . . ?
C2 C1 N1 Zn1 167.6(3) . . . . ?
C4 C5 N1 C1 0.9(5) . . . . ?
C4 C5 N1 Zn1 -168.2(3) . . . . ?
Zn1 O4 P1 O3 174.3(2) 6 . . . ?
Zn1 O4 P1 O1 -61.0(3) 6 . . . ?
Zn1 O4 P1 O2 54.9(2) 6 . . . ?
Zn1 O3 P1 O4 157.77(17) 7_557 . . . ?
Zn1 O3 P1 O1 31.3(2) 7_557 . . . ?
Zn1 O3 P1 O2 -82.9(2) 7_557 . . . ?
Zn1 O1 P1 O4 -68.70(18) . . . . ?
Zn1 O1 P1 O3 54.33(19) . . . . ?
Zn1 O1 P1 O2 172.07(14) . . . . ?

_refine_diff_density_max         0.546
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.073



