# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_szg258
_database_code_depnum_ccdc_archive 'CCDC 1964191'
loop_
_audit_author_name
_audit_author_address
'Zhen-Gang Sun'
;Liaoning Normal University
China
;
_audit_update_record             
;
2021-07-19 deposited with the CCDC.	2023-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 Cu N2 O6 P'
_chemical_formula_weight         479.90

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   10.0840(4)
_cell_length_b                   10.9173(4)
_cell_length_c                   18.4068(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2026.41(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7978
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      30.30

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_F_000             988
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.176
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.082
_exptl_absorpt_coefficient_mu    1.198
_shelx_estimated_absorpt_T_min   0.817
_shelx_estimated_absorpt_T_max   0.908
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11477
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.169
_diffrn_reflns_theta_max         26.489
_diffrn_reflns_theta_full        25.242
_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 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4172
_reflns_number_gt                3932
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_max     0.983
_reflns_Friedel_fraction_full    0.987

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0353P)²+0.0639P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1617 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.029(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4172
_refine_ls_number_parameters     291
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0216
_refine_ls_wR_factor_ref         0.0602
_refine_ls_wR_factor_gt          0.0593
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.05303(3) 0.34971(3) 0.18015(2) 0.02748(9) Uani 1 1 d . . . . .
P1 P 0.05440(6) 0.66896(5) 0.19035(3) 0.02452(13) Uani 1 1 d . . . . .
O1 O 0.0602(2) 0.54508(16) 0.22459(9) 0.0304(4) Uani 1 1 d . . . . .
O2 O 0.0434(2) 0.77852(17) 0.23931(10) 0.0351(4) Uani 1 1 d . . . . .
O3 O -0.0651(2) 0.66629(18) 0.13376(11) 0.0372(4) Uani 1 1 d . . . . .
O4 O 0.77353(19) 0.81701(18) 0.27791(11) 0.0363(5) Uani 1 1 d . . . . .
O5 O 0.7249(2) 0.6410(2) 0.33436(11) 0.0452(5) Uani 1 1 d . . . . .
N1 N -0.1196(2) 0.38329(19) 0.12878(12) 0.0292(5) Uani 1 1 d . . . . .
N2 N 0.1208(2) 0.3782(2) 0.07684(12) 0.0297(5) Uani 1 1 d . . . . .
C1 C 0.1986(3) 0.6954(3) 0.13372(15) 0.0303(6) Uani 1 1 d . . . . .
H1A H 0.2033 0.6305 0.0978 0.036 Uiso 1 1 calc R U . . .
H1B H 0.1859 0.7718 0.1078 0.036 Uiso 1 1 calc R U . . .
C2 C 0.3297(2) 0.7013(2) 0.17296(14) 0.0276(5) Uani 1 1 d . . . . .
C3 C 0.3709(3) 0.6081(3) 0.21897(16) 0.0339(6) Uani 1 1 d . . . . .
H3 H 0.3177 0.5394 0.2254 0.041 Uiso 1 1 calc R U . . .
C4 C 0.4136(3) 0.8014(3) 0.16429(16) 0.0366(7) Uani 1 1 d . . . . .
H4 H 0.3878 0.8654 0.1341 0.044 Uiso 1 1 calc R U . . .
C5 C 0.4904(3) 0.6165(3) 0.25520(16) 0.0335(6) Uani 1 1 d . . . . .
H5 H 0.5157 0.5534 0.2862 0.040 Uiso 1 1 calc R U . . .
C6 C 0.5358(3) 0.8079(2) 0.19996(15) 0.0364(6) Uani 1 1 d . . . . .
H6 H 0.5914 0.8745 0.1919 0.044 Uiso 1 1 calc R U . . .
C7 C 0.5741(3) 0.7167(2) 0.24668(13) 0.0274(5) Uani 1 1 d . . . . .
C8 C 0.7012(3) 0.7227(3) 0.28977(14) 0.0306(6) Uani 1 1 d . . . . .
C9 C -0.1174(4) 0.7788(4) 0.1035(2) 0.0586(10) Uani 1 1 d . . . . .
H9A H -0.2115 0.7848 0.1137 0.070 Uiso 1 1 calc R U . A 1
H9B H -0.0734 0.8486 0.1256 0.070 Uiso 1 1 calc R U . A 1
C10 C -0.0957(13) 0.7797(9) 0.0261(4) 0.095(4) Uani 0.574(12) 1 d . . P B 1
H10A H -0.0029 0.7905 0.0163 0.142 Uiso 0.574(12) 1 calc R U P B 1
H10B H -0.1448 0.8458 0.0047 0.142 Uiso 0.574(12) 1 calc R U P B 1
H10C H -0.1250 0.7034 0.0058 0.142 Uiso 0.574(12) 1 calc R U P B 1
C10' C -0.2229(14) 0.7579(9) 0.0531(6) 0.073(5) Uani 0.426(12) 1 d . . P B 2
H10D H -0.1894 0.7145 0.0116 0.110 Uiso 0.426(12) 1 calc R U P B 2
H10E H -0.2592 0.8350 0.0378 0.110 Uiso 0.426(12) 1 calc R U P B 2
H10F H -0.2910 0.7101 0.0760 0.110 Uiso 0.426(12) 1 calc R U P B 2
C11 C -0.2365(3) 0.3959(3) 0.16129(16) 0.0396(7) Uani 1 1 d . . . . .
H11 H -0.2418 0.3851 0.2113 0.048 Uiso 1 1 calc R U . . .
C12 C -0.3505(3) 0.4244(3) 0.1232(2) 0.0503(8) Uani 1 1 d . . . . .
H12 H -0.4311 0.4331 0.1473 0.060 Uiso 1 1 calc R U . . .
C13 C -0.3430(3) 0.4399(3) 0.04882(19) 0.0509(9) Uani 1 1 d . . . . .
H13 H -0.4187 0.4579 0.0220 0.061 Uiso 1 1 calc R U . . .
C14 C -0.2221(3) 0.4284(3) 0.01506(17) 0.0421(7) Uani 1 1 d . . . . .
H14 H -0.2147 0.4389 -0.0349 0.051 Uiso 1 1 calc R U . . .
C15 C -0.1109(3) 0.4007(3) 0.05665(15) 0.0298(6) Uani 1 1 d . . . . .
C16 C 0.0247(3) 0.3923(2) 0.02697(14) 0.0311(6) Uani 1 1 d . . . . .
C17 C 0.0539(4) 0.4006(3) -0.04690(15) 0.0440(7) Uani 1 1 d . . . . .
H17 H -0.0138 0.4070 -0.0810 0.053 Uiso 1 1 calc R U . . .
C18 C 0.1848(4) 0.3991(3) -0.06860(17) 0.0497(8) Uani 1 1 d . . . . .
H18 H 0.2065 0.4059 -0.1175 0.060 Uiso 1 1 calc R U . . .
C19 C 0.2835(3) 0.3873(3) -0.01693(17) 0.0440(7) Uani 1 1 d . . . . .
H19 H 0.3724 0.3871 -0.0304 0.053 Uiso 1 1 calc R U . . .
C20 C 0.2473(3) 0.3759(3) 0.05468(16) 0.0367(7) Uani 1 1 d . . . . .
H20 H 0.3136 0.3661 0.0893 0.044 Uiso 1 1 calc R U . . .
O1W O 0.9764(3) 0.5734(4) 0.37478(15) 0.0783(10) Uani 1 1 d D . . . .
H1WA H 0.8932(16) 0.581(4) 0.370(3) 0.088(16) Uiso 1 1 d D . . . .
H1WB H 1.004(4) 0.555(4) 0.3326(11) 0.065(12) 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
Cu1 O2 1.9358(19) 3_545 ?
Cu1 O4 1.9448(18) 3_645 ?
Cu1 N1 2.014(2) . ?
Cu1 N2 2.045(2) . ?
Cu1 O1 2.2855(17) . ?
P1 O1 1.4932(18) . ?
P1 O2 1.5018(18) . ?
P1 O3 1.5927(19) . ?
P1 C1 1.812(3) . ?
O2 Cu1 1.9358(19) 3 ?
O3 C9 1.448(4) . ?
O4 C8 1.281(3) . ?
O4 Cu1 1.9448(18) 3_655 ?
O5 C8 1.235(3) . ?
N1 C11 1.329(4) . ?
N1 C15 1.344(4) . ?
N2 C20 1.340(4) . ?
N2 C16 1.343(3) . ?
C1 C2 1.508(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.388(4) . ?
C2 C4 1.391(4) . ?
C3 C5 1.380(4) . ?
C3 H3 0.9300 . ?
C4 C6 1.398(4) . ?
C4 H4 0.9300 . ?
C5 C7 1.391(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.371(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.509(4) . ?
C9 C10' 1.431(9) . ?
C9 C10 1.442(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10' H10D 0.9600 . ?
C10' H10E 0.9600 . ?
C10' H10F 0.9600 . ?
C11 C12 1.382(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.374(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.391(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.476(4) . ?
C16 C17 1.394(4) . ?
C17 C18 1.380(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.382(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.373(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
O1W H1WA 0.849(14) . ?
O1W H1WB 0.848(13) . ?

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
O2 Cu1 O4 94.25(9) 3_545 3_645 ?
O2 Cu1 N1 89.91(9) 3_545 . ?
O4 Cu1 N1 175.38(9) 3_645 . ?
O2 Cu1 N2 160.27(9) 3_545 . ?
O4 Cu1 N2 95.54(9) 3_645 . ?
N1 Cu1 N2 79.89(9) . . ?
O2 Cu1 O1 96.68(7) 3_545 . ?
O4 Cu1 O1 90.06(8) 3_645 . ?
N1 Cu1 O1 91.45(8) . . ?
N2 Cu1 O1 100.39(8) . . ?
O1 P1 O2 118.09(11) . . ?
O1 P1 O3 106.79(11) . . ?
O2 P1 O3 110.57(11) . . ?
O1 P1 C1 110.85(12) . . ?
O2 P1 C1 106.11(12) . . ?
O3 P1 C1 103.51(11) . . ?
P1 O1 Cu1 133.86(10) . . ?
P1 O2 Cu1 144.72(14) . 3 ?
C9 O3 P1 120.7(2) . . ?
C8 O4 Cu1 126.31(18) . 3_655 ?
C11 N1 C15 119.2(2) . . ?
C11 N1 Cu1 125.02(19) . . ?
C15 N1 Cu1 115.68(19) . . ?
C20 N2 C16 118.7(2) . . ?
C20 N2 Cu1 126.77(19) . . ?
C16 N2 Cu1 114.33(18) . . ?
C2 C1 P1 115.77(18) . . ?
C2 C1 H1A 108.3 . . ?
P1 C1 H1A 108.3 . . ?
C2 C1 H1B 108.3 . . ?
P1 C1 H1B 108.3 . . ?
H1A C1 H1B 107.4 . . ?
C3 C2 C4 117.6(2) . . ?
C3 C2 C1 121.6(2) . . ?
C4 C2 C1 120.8(2) . . ?
C5 C3 C2 120.5(3) . . ?
C5 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C2 C4 C6 121.5(3) . . ?
C2 C4 H4 119.3 . . ?
C6 C4 H4 119.3 . . ?
C3 C5 C7 121.8(3) . . ?
C3 C5 H5 119.1 . . ?
C7 C5 H5 119.1 . . ?
C7 C6 C4 120.4(3) . . ?
C7 C6 H6 119.8 . . ?
C4 C6 H6 119.8 . . ?
C6 C7 C5 118.1(2) . . ?
C6 C7 C8 122.5(2) . . ?
C5 C7 C8 119.3(2) . . ?
O5 C8 O4 125.7(3) . . ?
O5 C8 C7 118.9(2) . . ?
O4 C8 C7 115.4(2) . . ?
C10' C9 O3 112.6(5) . . ?
C10 C9 O3 109.3(5) . . ?
C10 C9 H9A 109.8 . . ?
O3 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
O3 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C10' H10D 109.5 . . ?
C9 C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
C9 C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
N1 C11 C12 122.2(3) . . ?
N1 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C13 C12 C11 119.0(3) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C14 C13 C12 119.1(3) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 119.1(3) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
N1 C15 C14 121.5(3) . . ?
N1 C15 C16 114.7(2) . . ?
C14 C15 C16 123.8(2) . . ?
N2 C16 C17 121.5(3) . . ?
N2 C16 C15 115.0(2) . . ?
C17 C16 C15 123.5(3) . . ?
C18 C17 C16 118.9(3) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 119.4(3) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C20 C19 C18 118.5(3) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
N2 C20 C19 122.9(3) . . ?
N2 C20 H20 118.5 . . ?
C19 C20 H20 118.5 . . ?
H1WA O1W H1WB 104(4) . . ?

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_szg259
_database_code_depnum_ccdc_archive 'CCDC 1964192'
loop_
_audit_author_name
_audit_author_address
'Zhen-Gang Sun'
;Liaoning Normal University
China
;
_audit_update_record             
;
2019-11-07 deposited with the CCDC.	2023-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 Cu N2 O6 P'
_chemical_formula_weight         479.90

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   10.0728(9)
_cell_length_b                   10.8716(10)
_cell_length_c                   18.3600(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2010.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9965
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      30.96

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_F_000             988
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.883
_exptl_crystal_size_mid          0.743
_exptl_crystal_size_min          0.592
_exptl_absorpt_coefficient_mu    1.207
_shelx_estimated_absorpt_T_min   0.415
_shelx_estimated_absorpt_T_max   0.535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.358
_exptl_absorpt_correction_T_max  0.487
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10525
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.177
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3682
_reflns_number_gt                3581
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_max     0.962
_reflns_Friedel_fraction_full    0.963

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0359P)²+0.2740P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1468 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.025(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3682
_refine_ls_number_parameters     291
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0220
_refine_ls_wR_factor_ref         0.0591
_refine_ls_wR_factor_gt          0.0587
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.006
_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
Cu1 Cu 0.94709(3) 0.65028(3) 0.31982(2) 0.02400(10) Uani 1 1 d . . . . .
P1 P 0.94545(7) 0.33060(6) 0.30980(3) 0.02135(14) Uani 1 1 d . . . . .
O1 O 0.9400(2) 0.45452(16) 0.27541(10) 0.0271(4) Uani 1 1 d . . . . .
O2 O 0.9566(2) 0.22057(18) 0.26110(11) 0.0322(4) Uani 1 1 d . . . . .
O3 O 1.0649(2) 0.33333(18) 0.36625(11) 0.0337(5) Uani 1 1 d . . . . .
O4 O 0.2264(2) 0.18333(19) 0.22212(11) 0.0332(5) Uani 1 1 d . . . . .
O5 O 0.2753(2) 0.3592(2) 0.16546(12) 0.0419(5) Uani 1 1 d . . . . .
O1W O 0.9769(3) 0.9252(4) 0.37445(16) 0.0720(10) Uani 1 1 d D . . . .
N1 N 1.1194(2) 0.6164(2) 0.37122(13) 0.0260(5) Uani 1 1 d . . . . .
N2 N 0.8795(2) 0.6217(2) 0.42323(12) 0.0263(5) Uani 1 1 d . . . . .
C1 C 0.8011(3) 0.3041(3) 0.36657(15) 0.0271(6) Uani 1 1 d . . . . .
H1A H 0.8136 0.2273 0.3926 0.033 Uiso 1 1 calc R U . . .
H1B H 0.7963 0.3693 0.4026 0.033 Uiso 1 1 calc R U . . .
C2 C 0.6702(3) 0.2983(2) 0.32719(14) 0.0249(5) Uani 1 1 d . . . . .
C3 C 0.6289(3) 0.3917(3) 0.28083(17) 0.0315(6) Uani 1 1 d . . . . .
H3 H 0.6824 0.4604 0.2741 0.038 Uiso 1 1 calc R U . . .
C4 C 0.5858(3) 0.1985(3) 0.33596(17) 0.0338(7) Uani 1 1 d . . . . .
H4 H 0.6111 0.1344 0.3665 0.041 Uiso 1 1 calc R U . . .
C5 C 0.5096(3) 0.3836(3) 0.24475(16) 0.0309(6) Uani 1 1 d . . . . .
H5 H 0.4844 0.4471 0.2138 0.037 Uiso 1 1 calc R U . . .
C6 C 0.4643(3) 0.1919(3) 0.30019(16) 0.0338(7) Uani 1 1 d . . . . .
H6 H 0.4087 0.1250 0.3081 0.041 Uiso 1 1 calc R U . . .
C7 C 0.4260(3) 0.2834(2) 0.25326(14) 0.0246(6) Uani 1 1 d . . . . .
C8 C 0.2988(3) 0.2773(3) 0.21027(15) 0.0273(6) Uani 1 1 d . . . . .
C9 C 1.1188(4) 0.2206(4) 0.3960(2) 0.0539(10) Uani 1 1 d . . . . .
H9A H 1.0487 0.1760 0.4207 0.065 Uiso 1 1 calc R U . A 1
H9B H 1.1509 0.1695 0.3564 0.065 Uiso 1 1 calc R U . A 1
C10 C 1.2237(15) 0.2423(10) 0.4455(6) 0.081(5) Uani 0.453(13) 1 d . . P B 1
H10A H 1.2898 0.2929 0.4227 0.122 Uiso 0.453(13) 1 calc R U P B 1
H10B H 1.2627 0.1653 0.4595 0.122 Uiso 0.453(13) 1 calc R U P B 1
H10C H 1.1899 0.2834 0.4879 0.122 Uiso 0.453(13) 1 calc R U P B 1
C10' C 1.0944(14) 0.2220(9) 0.4744(4) 0.083(4) Uani 0.547(13) 1 d . . P B 2
H10D H 1.1179 0.3010 0.4938 0.124 Uiso 0.547(13) 1 calc R U P B 2
H10E H 1.1472 0.1595 0.4974 0.124 Uiso 0.547(13) 1 calc R U P B 2
H10F H 1.0021 0.2062 0.4835 0.124 Uiso 0.547(13) 1 calc R U P B 2
C11 C 1.2367(3) 0.6043(3) 0.33880(17) 0.0371(7) Uani 1 1 d . . . . .
H11 H 1.2420 0.6155 0.2887 0.044 Uiso 1 1 calc R U . . .
C12 C 1.3505(3) 0.5759(4) 0.3767(2) 0.0470(9) Uani 1 1 d . . . . .
H12 H 1.4310 0.5672 0.3524 0.056 Uiso 1 1 calc R U . . .
C13 C 1.3438(3) 0.5603(4) 0.4511(2) 0.0473(9) Uani 1 1 d . . . . .
H13 H 1.4198 0.5427 0.4779 0.057 Uiso 1 1 calc R U . . .
C14 C 1.2223(3) 0.5714(3) 0.48510(18) 0.0388(7) Uani 1 1 d . . . . .
H14 H 1.2147 0.5603 0.5352 0.047 Uiso 1 1 calc R U . . .
C15 C 1.1119(3) 0.5992(3) 0.44345(15) 0.0258(6) Uani 1 1 d . . . . .
C16 C 0.9749(3) 0.6075(3) 0.47300(14) 0.0275(6) Uani 1 1 d . . . . .
C17 C 0.9464(4) 0.5995(3) 0.54701(16) 0.0401(7) Uani 1 1 d . . . . .
H17 H 1.0143 0.5933 0.5811 0.048 Uiso 1 1 calc R U . . .
C18 C 0.8153(4) 0.6011(4) 0.56860(17) 0.0459(9) Uani 1 1 d . . . . .
H18 H 0.7936 0.5945 0.6177 0.055 Uiso 1 1 calc R U . . .
C19 C 0.7170(3) 0.6125(3) 0.51708(19) 0.0406(7) Uani 1 1 d . . . . .
H19 H 0.6281 0.6122 0.5307 0.049 Uiso 1 1 calc R U . . .
C20 C 0.7523(3) 0.6241(3) 0.44528(17) 0.0343(7) Uani 1 1 d . . . . .
H20 H 0.6858 0.6341 0.4106 0.041 Uiso 1 1 calc R U . . .
H1WA H 0.894(2) 0.942(6) 0.373(3) 0.11(2) Uiso 1 1 d D . . . .
H1WB H 1.004(5) 0.956(4) 0.3346(15) 0.077(15) 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
Cu1 O2 1.932(2) 3_755 ?
Cu1 O4 1.9428(19) 3_655 ?
Cu1 N1 2.010(2) . ?
Cu1 N2 2.041(2) . ?
Cu1 O1 2.2802(18) . ?
P1 O1 1.4889(19) . ?
P1 O2 1.4977(19) . ?
P1 O3 1.588(2) . ?
P1 C1 1.812(3) . ?
O2 Cu1 1.932(2) 3_745 ?
O3 C9 1.447(4) . ?
O4 C8 1.274(4) . ?
O4 Cu1 1.9428(19) 3_645 ?
O5 C8 1.235(4) . ?
O1W H1WA 0.852(14) . ?
O1W H1WB 0.848(14) . ?
N1 C11 1.329(4) . ?
N1 C15 1.341(4) . ?
N2 C16 1.336(4) . ?
N2 C20 1.344(4) . ?
C1 C2 1.505(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C4 1.388(4) . ?
C2 C3 1.389(4) . ?
C3 C5 1.375(4) . ?
C3 H3 0.9300 . ?
C4 C6 1.390(4) . ?
C4 H4 0.9300 . ?
C5 C7 1.385(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.372(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.506(4) . ?
C9 C10 1.414(10) . ?
C9 C10' 1.460(10) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10' H10D 0.9600 . ?
C10' H10E 0.9600 . ?
C10' H10F 0.9600 . ?
C11 C12 1.376(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.485(4) . ?
C16 C17 1.391(4) . ?
C17 C18 1.379(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.371(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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
O2 Cu1 O4 94.22(9) 3_755 3_655 ?
O2 Cu1 N1 90.00(10) 3_755 . ?
O4 Cu1 N1 175.34(9) 3_655 . ?
O2 Cu1 N2 160.60(9) 3_755 . ?
O4 Cu1 N2 95.55(9) 3_655 . ?
N1 Cu1 N2 79.84(10) . . ?
O2 Cu1 O1 96.31(8) 3_755 . ?
O4 Cu1 O1 90.15(8) 3_655 . ?
N1 Cu1 O1 91.37(8) . . ?
N2 Cu1 O1 100.37(8) . . ?
O1 P1 O2 118.18(11) . . ?
O1 P1 O3 106.73(11) . . ?
O2 P1 O3 110.35(12) . . ?
O1 P1 C1 110.97(13) . . ?
O2 P1 C1 106.06(13) . . ?
O3 P1 C1 103.62(12) . . ?
P1 O1 Cu1 133.77(11) . . ?
P1 O2 Cu1 144.37(14) . 3_745 ?
C9 O3 P1 121.0(2) . . ?
C8 O4 Cu1 126.57(19) . 3_645 ?
H1WA O1W H1WB 101(6) . . ?
C11 N1 C15 118.6(2) . . ?
C11 N1 Cu1 125.12(19) . . ?
C15 N1 Cu1 116.15(19) . . ?
C16 N2 C20 118.8(2) . . ?
C16 N2 Cu1 114.45(18) . . ?
C20 N2 Cu1 126.6(2) . . ?
C2 C1 P1 115.68(19) . . ?
C2 C1 H1A 108.4 . . ?
P1 C1 H1A 108.4 . . ?
C2 C1 H1B 108.4 . . ?
P1 C1 H1B 108.4 . . ?
H1A C1 H1B 107.4 . . ?
C4 C2 C3 117.3(3) . . ?
C4 C2 C1 120.9(2) . . ?
C3 C2 C1 121.8(2) . . ?
C5 C3 C2 120.7(3) . . ?
C5 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C2 C4 C6 121.7(3) . . ?
C2 C4 H4 119.2 . . ?
C6 C4 H4 119.2 . . ?
C3 C5 C7 121.8(3) . . ?
C3 C5 H5 119.1 . . ?
C7 C5 H5 119.1 . . ?
C7 C6 C4 120.4(3) . . ?
C7 C6 H6 119.8 . . ?
C4 C6 H6 119.8 . . ?
C6 C7 C5 118.0(3) . . ?
C6 C7 C8 122.4(2) . . ?
C5 C7 C8 119.5(2) . . ?
O5 C8 O4 125.5(3) . . ?
O5 C8 C7 118.7(2) . . ?
O4 C8 C7 115.7(2) . . ?
C10 C9 O3 112.5(5) . . ?
O3 C9 C10' 107.5(5) . . ?
C10 C9 H9A 109.1 . . ?
O3 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
O3 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C10' H10D 109.5 . . ?
C9 C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
C9 C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
N1 C11 C12 122.4(3) . . ?
N1 C11 H11 118.8 . . ?
C12 C11 H11 118.8 . . ?
C13 C12 C11 119.2(3) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 118.8(3) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C13 C14 C15 118.8(3) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
N1 C15 C14 122.1(3) . . ?
N1 C15 C16 113.9(2) . . ?
C14 C15 C16 123.9(3) . . ?
N2 C16 C17 121.8(3) . . ?
N2 C16 C15 115.2(2) . . ?
C17 C16 C15 123.0(3) . . ?
C18 C17 C16 118.5(3) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C17 C18 C19 119.6(3) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C18 118.9(3) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
N2 C20 C19 122.4(3) . . ?
N2 C20 H20 118.8 . . ?
C19 C20 H20 118.8 . . ?

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
C11 H11 O2 0.93 2.48 2.958(4) 112.3 3_755
C14 H14 O5 0.93 2.55 3.396(4) 151.6 2_665
C19 H19 O1W 0.93 2.35 3.160(4) 145.5 4_466
C20 H20 O4 0.93 2.65 3.147(4) 114.4 3_655

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_szg263
_database_code_depnum_ccdc_archive 'CCDC 1964196'
loop_
_audit_author_name
_audit_author_address
'Zhen-Gang Sun'
;Liaoning Normal University
China
;
_audit_update_record             
;
2021-07-19 deposited with the CCDC.	2023-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 Cd N2 O6 P'
_chemical_formula_weight         528.76

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   10.4713(3)
_cell_length_b                   10.7176(4)
_cell_length_c                   18.7468(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2103.90(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7992
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      30.07

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.069
_exptl_absorpt_coefficient_mu    1.154
_shelx_estimated_absorpt_T_min   0.786
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11985
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.173
_diffrn_reflns_theta_max         26.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4344
_reflns_number_gt                4145
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.997

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0258P)²+0.1018P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1744 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4344
_refine_ls_number_parameters     283
_refine_ls_number_restraints     343
_refine_ls_R_factor_all          0.0214
_refine_ls_R_factor_gt           0.0193
_refine_ls_wR_factor_ref         0.0471
_refine_ls_wR_factor_gt          0.0463
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001

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
Cd1 Cd 0.54274(2) 0.85893(2) 0.18256(2) 0.03271(7) Uani 1 1 d . U . . .
P1 P 0.41858(7) 0.68222(7) 0.31677(5) 0.03251(17) Uani 1 1 d . . . . .
O1 O 0.4206(2) 0.7971(2) 0.27128(13) 0.0443(6) Uani 1 1 d . . . . .
O2 O 0.4253(2) 0.5588(2) 0.27911(12) 0.0370(5) Uani 1 1 d . . . . .
O3 O 0.5329(3) 0.6836(2) 0.37179(15) 0.0524(7) Uani 1 1 d . . . . .
O4 O -0.2667(2) 0.8124(2) 0.22594(16) 0.0530(7) Uani 1 1 d . . . . .
O5 O -0.2244(2) 0.6309(3) 0.17363(14) 0.0568(7) Uani 1 1 d . . . . .
O6 O 0.5237(2) 0.6336(2) 0.14324(12) 0.0450(5) Uani 1 1 d . U . . .
H6A H 0.4741 0.5881 0.1776 0.054 Uiso 1 1 d R U . . .
H6B H 0.6074 0.5975 0.1399 0.054 Uiso 1 1 d R U . . .
N1 N 0.6074(3) 0.8850(3) 0.06254(14) 0.0375(6) Uani 1 1 d . . . . .
N2 N 0.3645(3) 0.9037(3) 0.11263(15) 0.0384(6) Uani 1 1 d . . . . .
C1 C 0.2792(3) 0.6896(3) 0.37308(18) 0.0375(7) Uani 1 1 d . U . . .
H1A H 0.2790 0.6172 0.4041 0.045 Uiso 1 1 calc R U . . .
H1B H 0.2857 0.7630 0.4031 0.045 Uiso 1 1 calc R U . . .
C2 C 0.1541(3) 0.6942(3) 0.33385(16) 0.0341(7) Uani 1 1 d . U . . .
C3 C 0.1150(3) 0.5983(4) 0.29012(19) 0.0437(8) Uani 1 1 d . U . . .
H3 H 0.1661 0.5279 0.2852 0.052 Uiso 1 1 calc R U . . .
C4 C 0.0720(4) 0.7944(4) 0.3418(2) 0.0521(10) Uani 1 1 d . U . . .
H4 H 0.0947 0.8592 0.3722 0.063 Uiso 1 1 calc R U . . .
C5 C 0.0001(4) 0.6057(4) 0.2532(2) 0.0444(8) Uani 1 1 d . U . . .
H5 H -0.0245 0.5398 0.2240 0.053 Uiso 1 1 calc R U . . .
C6 C -0.0424(4) 0.8007(3) 0.3059(2) 0.0512(9) Uani 1 1 d . U . . .
H6 H -0.0963 0.8684 0.3134 0.061 Uiso 1 1 calc R U . . .
C7 C -0.0780(3) 0.7083(3) 0.25895(18) 0.0370(7) Uani 1 1 d . U . . .
C8 C -0.1998(3) 0.7159(3) 0.21618(19) 0.0392(7) Uani 1 1 d . U . . .
C9 C 0.5849(6) 0.7978(5) 0.3981(3) 0.0911(18) Uani 1 1 d . U . . .
H9A H 0.6119 0.8489 0.3581 0.109 Uiso 1 1 calc R U . A 1
H9B H 0.5191 0.8431 0.4236 0.109 Uiso 1 1 calc R U . A 1
C10 C 0.6892(16) 0.7783(10) 0.4435(7) 0.110(5) Uani 0.628(17) 1 d . U P B 1
H10A H 0.6685 0.7143 0.4774 0.164 Uiso 0.628(17) 1 calc R U P B 1
H10B H 0.7085 0.8544 0.4684 0.164 Uiso 0.628(17) 1 calc R U P B 1
H10C H 0.7619 0.7530 0.4160 0.164 Uiso 0.628(17) 1 calc R U P B 1
C10' C 0.581(3) 0.7882(17) 0.4752(10) 0.105(6) Uani 0.372(17) 1 d . U P B 2
H10D H 0.4987 0.7595 0.4900 0.157 Uiso 0.372(17) 1 calc R U P B 2
H10E H 0.5979 0.8686 0.4958 0.157 Uiso 0.372(17) 1 calc R U P B 2
H10F H 0.6454 0.7302 0.4909 0.157 Uiso 0.372(17) 1 calc R U P B 2
C11 C 0.7273(3) 0.8726(4) 0.0398(2) 0.0463(8) Uani 1 1 d . U . . .
H11 H 0.7911 0.8606 0.0736 0.056 Uiso 1 1 calc R U . . .
C12 C 0.7615(4) 0.8767(4) -0.0307(2) 0.0539(10) Uani 1 1 d . U . . .
H12 H 0.8467 0.8714 -0.0443 0.065 Uiso 1 1 calc R U . . .
C13 C 0.6664(4) 0.8889(4) -0.0805(2) 0.0618(11) Uani 1 1 d . U . . .
H13 H 0.6862 0.8895 -0.1288 0.074 Uiso 1 1 calc R U . . .
C14 C 0.5413(4) 0.9002(4) -0.05862(19) 0.0541(9) Uani 1 1 d . U . . .
H14 H 0.4759 0.9080 -0.0919 0.065 Uiso 1 1 calc R U . . .
C15 C 0.5145(3) 0.8999(3) 0.01426(18) 0.0401(8) Uani 1 1 d . U . . .
C16 C 0.3817(3) 0.9150(3) 0.04162(19) 0.0395(7) Uani 1 1 d . U . . .
C17 C 0.2786(4) 0.9391(4) -0.0028(2) 0.0523(9) Uani 1 1 d . U . . .
H17 H 0.2903 0.9460 -0.0518 0.063 Uiso 1 1 calc R U . . .
C18 C 0.1590(4) 0.9526(5) 0.0265(2) 0.0657(12) Uani 1 1 d . U . . .
H18 H 0.0889 0.9672 -0.0028 0.079 Uiso 1 1 calc R U . . .
C19 C 0.1431(4) 0.9447(5) 0.0986(2) 0.0670(12) Uani 1 1 d . U . . .
H19 H 0.0633 0.9557 0.1194 0.080 Uiso 1 1 calc R U . . .
C20 C 0.2501(4) 0.9198(4) 0.1400(2) 0.0553(10) Uani 1 1 d . U . . .
H20 H 0.2403 0.9142 0.1892 0.066 Uiso 1 1 calc R U . . .


_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
Cd1 O1 2.200(2) . ?
Cd1 O4 2.212(2) 1_655 ?
Cd1 O2 2.284(2) 3_655 ?
Cd1 N2 2.331(3) . ?
Cd1 N1 2.366(3) . ?
Cd1 O6 2.533(2) . ?
P1 O1 1.498(2) . ?
P1 O2 1.501(2) . ?
P1 O3 1.580(2) . ?
P1 C1 1.803(3) . ?
O2 Cd1 2.284(2) 3_645 ?
O3 C9 1.427(6) . ?
O4 C8 1.262(4) . ?
O4 Cd1 2.212(2) 1_455 ?
O5 C8 1.238(4) . ?
O6 H6A 0.9600 . ?
O6 H6B 0.9600 . ?
N1 C11 1.333(4) . ?
N1 C15 1.338(4) . ?
N2 C20 1.315(5) . ?
N2 C16 1.349(4) . ?
C1 C2 1.503(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.376(5) . ?
C2 C4 1.383(5) . ?
C3 C5 1.391(5) . ?
C3 H3 0.9300 . ?
C4 C6 1.375(5) . ?
C4 H4 0.9300 . ?
C5 C7 1.374(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.509(5) . ?
C9 C10' 1.450(19) . ?
C9 C10 1.400(11) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10' H10D 0.9600 . ?
C10' H10E 0.9600 . ?
C10' H10F 0.9600 . ?
C11 C12 1.369(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.371(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.395(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.490(5) . ?
C16 C17 1.387(5) . ?
C17 C18 1.376(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.364(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.388(6) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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 Cd1 O4 100.29(11) . 1_655 ?
O1 Cd1 O2 97.46(9) . 3_655 ?
O4 Cd1 O2 87.92(9) 1_655 3_655 ?
O1 Cd1 N2 91.24(10) . . ?
O4 Cd1 N2 167.34(11) 1_655 . ?
O2 Cd1 N2 95.81(9) 3_655 . ?
O1 Cd1 N1 157.01(9) . . ?
O4 Cd1 N1 96.79(10) 1_655 . ?
O2 Cd1 N1 98.44(9) 3_655 . ?
N2 Cd1 N1 70.72(10) . . ?
O1 Cd1 O6 83.51(8) . . ?
O4 Cd1 O6 87.88(9) 1_655 . ?
O2 Cd1 O6 175.79(8) 3_655 . ?
N2 Cd1 O6 88.25(9) . . ?
N1 Cd1 O6 81.85(8) . . ?
O1 P1 O2 117.12(14) . . ?
O1 P1 O3 110.68(14) . . ?
O2 P1 O3 106.27(14) . . ?
O1 P1 C1 107.99(15) . . ?
O2 P1 C1 110.59(15) . . ?
O3 P1 C1 103.34(15) . . ?
P1 O1 Cd1 133.33(14) . . ?
P1 O2 Cd1 133.26(13) . 3_645 ?
C9 O3 P1 121.5(3) . . ?
C8 O4 Cd1 129.2(2) . 1_455 ?
Cd1 O6 H6A 109.4 . . ?
Cd1 O6 H6B 109.4 . . ?
H6A O6 H6B 109.5 . . ?
C11 N1 C15 118.7(3) . . ?
C11 N1 Cd1 124.2(2) . . ?
C15 N1 Cd1 116.7(2) . . ?
C20 N2 C16 119.7(3) . . ?
C20 N2 Cd1 122.5(2) . . ?
C16 N2 Cd1 117.8(2) . . ?
C2 C1 P1 114.9(2) . . ?
C2 C1 H1A 108.5 . . ?
P1 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
P1 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
C3 C2 C4 117.3(3) . . ?
C3 C2 C1 121.7(3) . . ?
C4 C2 C1 121.0(3) . . ?
C2 C3 C5 120.7(3) . . ?
C2 C3 H3 119.6 . . ?
C5 C3 H3 119.6 . . ?
C6 C4 C2 121.8(3) . . ?
C6 C4 H4 119.1 . . ?
C2 C4 H4 119.1 . . ?
C7 C5 C3 121.4(4) . . ?
C7 C5 H5 119.3 . . ?
C3 C5 H5 119.3 . . ?
C4 C6 C7 120.8(3) . . ?
C4 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C5 C7 C6 117.7(3) . . ?
C5 C7 C8 120.3(3) . . ?
C6 C7 C8 122.0(3) . . ?
O5 C8 O4 125.5(3) . . ?
O5 C8 C7 118.6(3) . . ?
O4 C8 C7 115.9(3) . . ?
C10' C9 O3 105.9(9) . . ?
C10 C9 O3 112.3(6) . . ?
C10 C9 H9A 109.1 . . ?
O3 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
O3 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C10' H10D 109.5 . . ?
C9 C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
C9 C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
N1 C11 C12 123.5(4) . . ?
N1 C11 H11 118.3 . . ?
C12 C11 H11 118.3 . . ?
C11 C12 C13 118.0(4) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
C12 C13 C14 119.7(4) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C15 118.9(4) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
N1 C15 C14 121.1(3) . . ?
N1 C15 C16 117.3(3) . . ?
C14 C15 C16 121.7(3) . . ?
N2 C16 C17 120.3(3) . . ?
N2 C16 C15 117.0(3) . . ?
C17 C16 C15 122.6(3) . . ?
C18 C17 C16 119.3(4) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C19 C18 C17 120.0(4) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 117.9(4) . . ?
C18 C19 H19 121.1 . . ?
C20 C19 H19 121.1 . . ?
N2 C20 C19 122.8(4) . . ?
N2 C20 H20 118.6 . . ?
C19 C20 H20 118.6 . . ?

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.045

