# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_Zn_BCP_Et
_database_code_depnum_ccdc_archive 'CCDC 1985570'
loop_
_audit_author_name
_audit_author_address
'Christoph Janiak'
;University of Duesseldorf
Germany
;
_audit_update_record             
;
2020-02-21 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H7 O5.50 P1.25 Zn, C H2'
_chemical_formula_sum            'C9 H9 O5.50 P1.25 Zn'
_chemical_formula_weight         309.24

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'
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      tetragonal
_space_group_IT_number           139
_space_group_name_H-M_alt        'I 4/m m m'
_space_group_name_Hall           '-I 4 2'

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

_cell_length_a                   21.4445(11)
_cell_length_b                   21.4445(11)
_cell_length_c                   9.3118(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4282.2(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    260(2)
_cell_measurement_reflns_used    16531
_cell_measurement_theta_min      1.75
_cell_measurement_theta_max      32.03

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.959
_exptl_crystal_F_000             1246
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.244
_shelx_estimated_absorpt_T_min   0.746
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6365
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      260(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47819
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.343
_diffrn_reflns_theta_max         32.065
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2112
_reflns_number_gt                1636
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 4.5 (Brandenburg, 2018)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.1041P)²+8.4314P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2112
_refine_ls_number_parameters     73
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.1867
_refine_ls_wR_factor_gt          0.1666
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.101
_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
Zn1 Zn 0.500000 0.500000 0.33857(7) 0.0240(2) Uani 1 8 d S T P . .
Zn2 Zn 0.500000 1.000000 0.250000 0.0288(2) Uani 1 8 d S T P . .
O1 O 0.500000 0.92634(14) 0.3645(4) 0.0676(11) Uani 1 2 d S T P . .
P1 P 0.52771(13) 0.90154(9) 0.500000 0.0472(5) Uani 0.5 2 d S T P . .
O11 O 0.5987(5) 0.9153(5) 0.500000 0.097(3) Uiso 0.5 2 d DS U P . .
C11 C 0.6486(10) 0.8942(12) 0.427(2) 0.118(8) Uani 0.25 1 d D U P . .
H11A H 0.646517 0.906695 0.326786 0.141 Uiso 0.25 1 calc R U P . .
H11B H 0.651209 0.849116 0.431847 0.141 Uiso 0.25 1 calc R U P . .
C12 C 0.7033(14) 0.9239(18) 0.500000 0.256(18) Uani 0.5 2 d DS TU P . .
H12A H 0.741066 0.910947 0.453515 0.384 Uiso 0.25 1 calc R U P . .
H12B H 0.699532 0.968407 0.500000 0.384 Uiso 0.5 2 calc R U P . .
H12C H 0.704192 0.911225 0.598881 0.384 Uiso 0.25 1 calc R U P . .
C1 C 0.500000 0.8187(3) 0.500000 0.118(5) Uani 1 4 d S TU P . .
C2 C 0.500000 0.7860(2) 0.6270(6) 0.103(3) Uani 1 2 d S TU P . .
H2 H 0.500000 0.807538 0.713776 0.124 Uiso 1 2 calc R U P . .
C3 C 0.500000 0.7219(2) 0.6272(5) 0.083(2) Uani 1 2 d S TU P . .
H3 H 0.500000 0.700443 0.714001 0.099 Uiso 1 2 calc R U P . .
C4 C 0.500000 0.6893(3) 0.500000 0.0519(15) Uani 1 4 d S TU P . .
C5 C 0.500000 0.6195(2) 0.500000 0.0424(11) Uani 1 4 d S T P . .
O4 O 0.500000 0.59335(13) 0.3803(4) 0.0587(9) Uani 1 2 d S T P . .
O1X O 0.500000 0.500000 0.1326(6) 0.0458(13) Uani 1 8 d S T P . .
P1X P 0.500000 0.4640(3) 0.000000 0.073(3) Uani 0.25 4 d S 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
Zn1 O1X 1.918(5) . ?
Zn1 O4 2.039(3) . ?
Zn1 O4 2.039(3) 4_565 ?
Zn1 O4 2.039(3) 3_655 ?
Zn1 O4 2.039(3) 2_665 ?
Zn1 Zn1 3.0064(13) 17_666 ?
Zn2 O1 1.906(3) 27_465 ?
Zn2 O1 1.906(3) 2_675 ?
Zn2 O1 1.906(3) 28_655 ?
Zn2 O1 1.906(3) . ?
O1 P1 1.493(3) . ?
O1 P1 1.493(3) 5_656 ?
P1 P1 1.188(5) 5_656 ?
P1 O11 1.552(11) . ?
P1 C1 1.873(7) . ?
O11 C11 1.347(16) 18_556 ?
O11 C11 1.347(16) . ?
C11 C12 1.497(18) . ?
C1 C2 1.375(6) 18_556 ?
C1 C2 1.375(6) . ?
C2 C3 1.375(6) . ?
C3 C4 1.376(6) . ?
C4 C5 1.497(7) . ?
C5 O4 1.247(4) 18_556 ?
C5 O4 1.247(4) . ?
O1X P1X 1.456(6) . ?
O1X P1X 1.456(6) 19_565 ?
O1X P1X 1.456(6) 3_655 ?
O1X P1X 1.456(6) 17_665 ?
P1X P1X 1.093(10) 3_655 ?
P1X P1X 1.093(10) 19_565 ?
P1X P1X 1.545(14) 17_665 ?

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
O1X Zn1 O4 100.99(10) . . ?
O1X Zn1 O4 100.99(10) . 4_565 ?
O4 Zn1 O4 87.92(4) . 4_565 ?
O1X Zn1 O4 100.99(10) . 3_655 ?
O4 Zn1 O4 87.92(4) . 3_655 ?
O4 Zn1 O4 158.03(19) 4_565 3_655 ?
O1X Zn1 O4 100.99(10) . 2_665 ?
O4 Zn1 O4 158.03(19) . 2_665 ?
O4 Zn1 O4 87.92(4) 4_565 2_665 ?
O4 Zn1 O4 87.92(4) 3_655 2_665 ?
O1X Zn1 Zn1 180.0 . 17_666 ?
O4 Zn1 Zn1 79.01(10) . 17_666 ?
O4 Zn1 Zn1 79.01(10) 4_565 17_666 ?
O4 Zn1 Zn1 79.01(10) 3_655 17_666 ?
O4 Zn1 Zn1 79.01(10) 2_665 17_666 ?
O1 Zn2 O1 108.23(10) 27_465 2_675 ?
O1 Zn2 O1 112.0(2) 27_465 28_655 ?
O1 Zn2 O1 108.23(11) 2_675 28_655 ?
O1 Zn2 O1 108.23(11) 27_465 . ?
O1 Zn2 O1 112.0(2) 2_675 . ?
O1 Zn2 O1 108.23(10) 28_655 . ?
P1 O1 P1 46.9(2) . 5_656 ?
P1 O1 Zn2 140.18(19) . . ?
P1 O1 Zn2 140.19(19) 5_656 . ?
P1 P1 O1 66.55(11) 5_656 18_556 ?
P1 P1 O1 66.55(11) 5_656 . ?
O1 P1 O1 115.4(2) 18_556 . ?
P1 P1 O11 169.0(4) 5_656 . ?
O1 P1 O11 108.8(2) 18_556 . ?
O1 P1 O11 108.8(2) . . ?
P1 P1 C1 71.50(11) 5_656 . ?
O1 P1 C1 102.21(15) 18_556 . ?
O1 P1 C1 102.21(15) . . ?
O11 P1 C1 119.5(4) . . ?
C11 O11 C11 61(2) 18_556 . ?
C11 O11 P1 135.7(13) 18_556 . ?
C11 O11 P1 135.7(13) . . ?
O11 C11 C12 104(2) . . ?
C2 C1 C2 118.7(6) 18_556 . ?
C2 C1 P1 118.9(3) 18_556 5_656 ?
C2 C1 P1 118.9(3) . 5_656 ?
C2 C1 P1 118.9(3) 18_556 . ?
C2 C1 P1 118.9(3) . . ?
C1 C2 C3 120.7(5) . . ?
C2 C3 C4 120.5(5) . . ?
C3 C4 C3 118.8(5) 18_556 . ?
C3 C4 C5 120.6(3) 18_556 . ?
C3 C4 C5 120.6(3) . . ?
O4 C5 O4 126.6(5) 18_556 . ?
O4 C5 C4 116.7(2) 18_556 . ?
O4 C5 C4 116.7(2) . . ?
C5 O4 Zn1 127.7(3) . . ?
P1X O1X P1X 64.1(5) 19_565 3_655 ?
P1X O1X P1X 64.1(5) . 17_665 ?
P1X O1X Zn1 148.0(3) . . ?
P1X O1X Zn1 148.0(3) 19_565 . ?
P1X O1X Zn1 148.0(3) 3_655 . ?
P1X O1X Zn1 148.0(3) 17_665 . ?
P1X P1X P1X 90.002(1) 3_655 19_565 ?
P1X P1X O1X 67.97(17) 3_655 . ?
P1X P1X O1X 67.97(17) 19_565 . ?
P1X P1X O1X 67.97(17) 3_655 17_665 ?
P1X P1X O1X 67.97(17) 19_565 17_665 ?
O1X P1X O1X 115.9(5) . 17_665 ?
P1X P1X P1X 45.001(1) 3_655 17_665 ?
P1X P1X P1X 45.001(1) 19_565 17_665 ?
O1X P1X P1X 58.0(3) . 17_665 ?
O1X P1X P1X 58.0(3) 17_665 17_665 ?

_refine_diff_density_max         1.722
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.141



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: N,N-dimethylformamide'
####################################################################### 
# 
# 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_znetd
_database_code_depnum_ccdc_archive 'CCDC 1985571'
loop_
_audit_author_name
_audit_author_address
'Christoph Janiak'
;University of Duesseldorf
Germany
;
_audit_update_record             
;
2020-02-21 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C10.50 H12 N0.50 O5 P Zn), 2(C4 H9 N O)'
_chemical_formula_sum            'C29 H42 N3 O12 P2 Zn2'
_chemical_formula_weight         817.33

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      tetragonal
_space_group_IT_number           87
_space_group_name_H-M_alt        'I 4/m'
_space_group_name_Hall           '-I 4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x, z'
'y, -x, z'
'-x, -y, z'
'x+1/2, y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'y, -x, -z'
'-y, x, -z'
'x, y, -z'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'

_cell_length_a                   19.912(4)
_cell_length_b                   19.912(4)
_cell_length_c                   9.5338(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3779.9(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4046
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      23.54

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_F_000             1692
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.413
_shelx_estimated_absorpt_T_min   0.765
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6270
_exptl_absorpt_correction_T_max  0.7445
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23360
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.046
_diffrn_reflns_theta_max         26.324
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 0.948
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.948
_reflns_number_total             1947
_reflns_number_gt                1145
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4.5 (Brandenburg, 2018)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1387P)²] 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         1947
_refine_ls_number_parameters     120
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0748
_refine_ls_wR_factor_ref         0.2229
_refine_ls_wR_factor_gt          0.2041
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.982
_refine_ls_shift/su_max          0.010
_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
Zn1 Zn 0.500000 0.000000 0.750000 0.0493(4) Uani 1 4 d S T P . .
Zn2 Zn 0.500000 0.500000 0.65113(10) 0.0538(5) Uani 1 4 d S T P B .
P P 0.58682(10) 0.07580(11) 0.500000 0.0545(6) Uani 1 2 d S T P . .
O1 O 0.5633(3) 0.0464(2) 0.6343(4) 0.0847(14) Uani 1 1 d . . . . .
O2 O 0.6626(4) 0.0675(5) 0.5241(18) 0.077(5) Uani 0.5 1 d D . P A -1
C7 C 0.7057(11) 0.0723(18) 0.410(2) 0.200(12) Uiso 0.5 1 d D . P A -1
H71 H 0.703370 0.117642 0.372482 0.240 Uiso 0.5 1 calc R U P A -1
H72 H 0.690177 0.042031 0.336776 0.240 Uiso 0.5 1 calc R U P A -1
C8 C 0.7775(12) 0.0563(13) 0.442(3) 0.173(11) Uiso 0.5 1 d D . P A -1
H81 H 0.804093 0.060662 0.358767 0.208 Uiso 0.5 1 calc R U P A -1
H82 H 0.793860 0.086752 0.512430 0.208 Uiso 0.5 1 calc R U P A -1
H83 H 0.780650 0.011048 0.476681 0.208 Uiso 0.5 1 calc R U P A -1
C1 C 0.5712(4) 0.1641(4) 0.500000 0.0540(18) Uani 1 2 d S T P A .
C2 C 0.5670(5) 0.1992(4) 0.6218(6) 0.091(2) Uani 1 1 d . . . . .
H2 H 0.573227 0.176766 0.706395 0.109 Uiso 1 1 calc R U . A .
C3 C 0.5540(5) 0.2664(4) 0.6233(6) 0.097(3) Uani 1 1 d . . . . .
H3 H 0.549629 0.288970 0.708311 0.117 Uiso 1 1 calc R U . . .
C4 C 0.5473(5) 0.3007(4) 0.500000 0.063(2) Uani 1 2 d S T P . .
C5 C 0.5308(5) 0.3756(5) 0.500000 0.068(2) Uani 1 2 d S T P . .
O3 O 0.5248(3) 0.4031(2) 0.6149(4) 0.0905(16) Uani 1 1 d . . . . .
N1 N 0.500000 0.500000 0.8650(7) 0.0426(18) Uani 1 4 d DS T P . .
C6A C 0.5675(7) 0.513(3) 0.920(2) 0.047(3) Uiso 0.25 1 d D . P B -1
H61A H 0.581732 0.556789 0.885256 0.057 Uiso 0.25 1 d R U P B -1
H62A H 0.598635 0.479645 0.885256 0.057 Uiso 0.25 1 d R U P B -1
C6B C 0.457(2) 0.5573(17) 0.915(2) 0.047(3) Uiso 0.25 1 d D . P B -1
H61B H 0.411893 0.551245 0.879014 0.057 Uiso 0.25 1 d R U P B -1
H62B H 0.474716 0.599410 0.879014 0.057 Uiso 0.25 1 d R U P B -1
C6C C 0.473(3) 0.4384(12) 0.923(2) 0.047(3) Uiso 0.25 1 d D . P B -1
H61C H 0.498841 0.400892 0.888337 0.057 Uiso 0.25 1 d R U P B -1
H62C H 0.426970 0.433536 0.888337 0.057 Uiso 0.25 1 d R U P B -1
O1S O 0.6391(13) 0.1219(10) 1.012(9) 0.311(13) Uiso 0.5 1 d D . P C -1
C2S C 0.6670(16) 0.1804(11) 1.006(5) 0.272(14) Uiso 0.5 1 d D . P C -1
C1S C 0.6328(11) 0.2465(9) 1.035(3) 0.166(10) Uiso 0.5 1 d D . P C -1
H11S H 0.664251 0.282512 1.022898 0.200 Uiso 0.5 1 calc R U P C -1
H12S H 0.595835 0.252294 0.971537 0.200 Uiso 0.5 1 calc R U P C -1
H13S H 0.616359 0.246701 1.129854 0.200 Uiso 0.5 1 calc R U P C -1
N1S N 0.7224(13) 0.1837(14) 0.926(4) 0.284(18) Uiso 0.5 1 d D . P C -1
C3S C 0.7650(17) 0.1242(17) 0.916(6) 0.37(3) Uiso 0.5 1 d D . P C -1
H31S H 0.802504 0.133487 0.855913 0.442 Uiso 0.5 1 calc R U P C -1
H32S H 0.780971 0.112461 1.007858 0.442 Uiso 0.5 1 calc R U P C -1
H33S H 0.739483 0.087517 0.878180 0.442 Uiso 0.5 1 calc R U P C -1
C4S C 0.744(2) 0.2487(19) 0.872(8) 0.38(3) Uiso 0.5 1 d D . P C -1
H41S H 0.784398 0.242837 0.816880 0.455 Uiso 0.5 1 calc R U P C -1
H42S H 0.709696 0.267670 0.814282 0.455 Uiso 0.5 1 calc R U P C -1
H43S H 0.753650 0.278312 0.948882 0.455 Uiso 0.5 1 calc R U P C -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 1.913(4) . ?
Zn1 O1 1.913(4) 4_655 ?
Zn1 O1 1.913(4) 15_546 ?
Zn1 O1 1.913(4) 14_556 ?
Zn2 O3 2.021(5) . ?
Zn2 O3 2.021(5) 3_565 ?
Zn2 O3 2.021(5) 2_655 ?
Zn2 O3 2.021(5) 4_665 ?
Zn2 N1 2.039(7) . ?
P O1 1.484(4) 12_556 ?
P O1 1.484(4) . ?
P O2 1.536(9) . ?
P C1 1.786(8) . ?
O2 C7 1.392(10) . ?
C7 C8 1.498(10) . ?
C7 H71 0.9700 . ?
C7 H72 0.9700 . ?
C8 H81 0.9600 . ?
C8 H82 0.9600 . ?
C8 H83 0.9600 . ?
C1 C2 1.357(8) 12_556 ?
C1 C2 1.357(8) . ?
C2 C3 1.364(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.527(13) . ?
C5 O3 1.231(6) . ?
C5 O3 1.231(6) 12_556 ?
N1 C6C 1.451(13) . ?
N1 C6A 1.466(13) . ?
N1 C6B 1.502(13) . ?
C6A C6A 1.53(4) 12_557 ?
C6A H61A 0.9700 . ?
C6A H62A 0.9699 . ?
C6B C6B 1.63(4) 12_557 ?
C6B H61B 0.9700 . ?
C6B H62B 0.9700 . ?
C6C C6C 1.47(4) 12_557 ?
C6C H61C 0.9700 . ?
C6C H62C 0.9700 . ?
O1S C2S 1.293(10) . ?
C2S N1S 1.342(10) . ?
C2S C1S 1.508(9) . ?
C1S H11S 0.9600 . ?
C1S H12S 0.9600 . ?
C1S H13S 0.9600 . ?
N1S C3S 1.460(9) . ?
N1S C4S 1.460(9) . ?
C3S H31S 0.9600 . ?
C3S H32S 0.9600 . ?
C3S H33S 0.9600 . ?
C4S H41S 0.9600 . ?
C4S H42S 0.9600 . ?
C4S H43S 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O1 109.6(3) . 4_655 ?
O1 Zn1 O1 109.40(15) . 15_546 ?
O1 Zn1 O1 109.40(15) 4_655 15_546 ?
O1 Zn1 O1 109.40(15) . 14_556 ?
O1 Zn1 O1 109.40(15) 4_655 14_556 ?
O1 Zn1 O1 109.6(3) 15_546 14_556 ?
O3 Zn2 O3 88.33(4) . 3_565 ?
O3 Zn2 O3 88.33(4) . 2_655 ?
O3 Zn2 O3 160.3(2) 3_565 2_655 ?
O3 Zn2 O3 160.3(2) . 4_665 ?
O3 Zn2 O3 88.33(4) 3_565 4_665 ?
O3 Zn2 O3 88.33(4) 2_655 4_665 ?
O3 Zn2 N1 99.83(12) . . ?
O3 Zn2 N1 99.83(12) 3_565 . ?
O3 Zn2 N1 99.83(12) 2_655 . ?
O3 Zn2 N1 99.83(12) 4_665 . ?
O1 P O1 119.4(4) 12_556 . ?
O1 P O2 113.3(6) 12_556 . ?
O1 P O2 97.9(6) . . ?
O1 P C1 109.5(2) 12_556 . ?
O1 P C1 109.5(2) . . ?
O2 P C1 106.1(4) . . ?
P O1 Zn1 153.6(4) . . ?
C7 O2 P 118.8(15) . . ?
O2 C7 C8 114(2) . . ?
O2 C7 H71 108.7 . . ?
C8 C7 H71 108.7 . . ?
O2 C7 H72 108.7 . . ?
C8 C7 H72 108.7 . . ?
H71 C7 H72 107.6 . . ?
C7 C8 H81 109.5 . . ?
C7 C8 H82 109.5 . . ?
H81 C8 H82 109.5 . . ?
C7 C8 H83 109.5 . . ?
H81 C8 H83 109.5 . . ?
H82 C8 H83 109.5 . . ?
C2 C1 C2 117.6(8) 12_556 . ?
C2 C1 P 121.1(4) 12_556 . ?
C2 C1 P 121.1(4) . . ?
C1 C2 C3 121.7(6) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C2 C3 C4 119.9(6) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C3 118.9(8) 12_556 . ?
C3 C4 C5 120.5(4) 12_556 . ?
C3 C4 C5 120.5(4) . . ?
O3 C5 O3 125.7(9) . 12_556 ?
O3 C5 C4 117.1(4) . . ?
O3 C5 C4 117.1(4) 12_556 . ?
C5 O3 Zn2 127.0(5) . . ?
C6C N1 C6A 111.2(8) . . ?
C6C N1 C6B 108.0(8) . . ?
C6A N1 C6B 105.8(8) . . ?
C6C N1 Zn2 112.3(8) . . ?
C6A N1 Zn2 110.9(9) . . ?
C6B N1 Zn2 108.4(8) . . ?
N1 C6A C6A 110.9(9) . 12_557 ?
N1 C6A H61A 107.9 . . ?
C6A C6A H61A 109.9 12_557 . ?
N1 C6A H62A 109.9 . . ?
C6A C6A H62A 109.9 12_557 . ?
H61A C6A H62A 108.3 . . ?
N1 C6B C6B 108.4(8) . 12_557 ?
N1 C6B H61B 108.8 . . ?
C6B C6B H61B 110.5 12_557 . ?
N1 C6B H62B 109.9 . . ?
C6B C6B H62B 110.5 12_557 . ?
H61B C6B H62B 108.7 . . ?
N1 C6C C6C 112.3(8) . 12_557 ?
N1 C6C H61C 108.6 . . ?
C6C C6C H61C 109.8 12_557 . ?
N1 C6C H62C 108.0 . . ?
C6C C6C H62C 109.8 12_557 . ?
H61C C6C H62C 108.2 . . ?
O1S C2S N1S 115.1(18) . . ?
O1S C2S C1S 125.6(17) . . ?
N1S C2S C1S 115.8(14) . . ?
C2S C1S H11S 109.5 . . ?
C2S C1S H12S 109.5 . . ?
H11S C1S H12S 109.5 . . ?
C2S C1S H13S 109.5 . . ?
H11S C1S H13S 109.5 . . ?
H12S C1S H13S 109.5 . . ?
C2S N1S C3S 118.3(15) . . ?
C2S N1S C4S 119.3(14) . . ?
C3S N1S C4S 121.5(14) . . ?
N1S C3S H31S 109.5 . . ?
N1S C3S H32S 109.5 . . ?
H31S C3S H32S 109.5 . . ?
N1S C3S H33S 109.5 . . ?
H31S C3S H33S 109.5 . . ?
H32S C3S H33S 109.5 . . ?
N1S C4S H41S 109.5 . . ?
N1S C4S H42S 109.5 . . ?
H41S C4S H42S 109.5 . . ?
N1S C4S H43S 109.5 . . ?
H41S C4S H43S 109.5 . . ?
H42S C4S H43S 109.5 . . ?

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
O1 P O1 Zn1 -28.7(11) 12_556 . . . ?
O2 P O1 Zn1 -151.2(8) . . . . ?
C1 P O1 Zn1 98.5(8) . . . . ?
O1 P O2 C7 37(2) 12_556 . . . ?
O1 P O2 C7 163.5(19) . . . . ?
C1 P O2 C7 -84(2) . . . . ?
P O2 C7 C8 -173.9(18) . . . . ?
O1 P C1 C2 -25.7(8) 12_556 . . 12_556 ?
O1 P C1 C2 -158.3(7) . . . 12_556 ?
O2 P C1 C2 97.0(10) . . . 12_556 ?
O1 P C1 C2 158.3(7) 12_556 . . . ?
O1 P C1 C2 25.7(8) . . . . ?
O2 P C1 C2 -79.0(10) . . . . ?
C2 C1 C2 C3 5.0(16) 12_556 . . . ?
P C1 C2 C3 -178.9(7) . . . . ?
C1 C2 C3 C4 -2.5(15) . . . . ?
C2 C3 C4 C3 -0.1(18) . . . 12_556 ?
C2 C3 C4 C5 178.3(8) . . . . ?
C3 C4 C5 O3 179.3(9) 12_556 . . . ?
C3 C4 C5 O3 0.9(14) . . . . ?
C3 C4 C5 O3 -0.9(14) 12_556 . . 12_556 ?
C3 C4 C5 O3 -179.3(9) . . . 12_556 ?
O3 C5 O3 Zn2 2.6(15) 12_556 . . . ?
C4 C5 O3 Zn2 -177.6(5) . . . . ?
C6C N1 C6A C6A -54.3(9) . . . 12_557 ?
C6B N1 C6A C6A 62.7(9) . . . 12_557 ?
Zn2 N1 C6A C6A 180.000(2) . . . 12_557 ?
C6C N1 C6B C6B 58.1(9) . . . 12_557 ?
C6A N1 C6B C6B -61.0(9) . . . 12_557 ?
Zn2 N1 C6B C6B 180.000(8) . . . 12_557 ?
C6A N1 C6C C6C 55.0(10) . . . 12_557 ?
C6B N1 C6C C6C -60.6(10) . . . 12_557 ?
Zn2 N1 C6C C6C 180.000(4) . . . 12_557 ?
O1S C2S N1S C3S -31(6) . . . . ?
C1S C2S N1S C3S 168(4) . . . . ?
O1S C2S N1S C4S 159(6) . . . . ?
C1S C2S N1S C4S -1(7) . . . . ?

_refine_diff_density_max         0.805
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.144


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: N,N-dimethylacetamide'
