# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_4nidpad
_database_code_depnum_ccdc_archive 'CCDC 1815204'
_audit_update_record             
;
2018-01-07 deposited with the CCDC.
2018-03-26 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         
'C26 H36 Li2 N6 Ni2 O11 P2, Li, Cl O4, 11(H2 O)'
_chemical_formula_sum            'C26 H58 Cl Li3 N6 Ni2 O26 P2'
_chemical_formula_weight         1106.41

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'
Li Li -0.0003 0.0001 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   9.3666(4)
_cell_length_b                   35.0692(15)
_cell_length_c                   14.1635(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.461(2)
_cell_angle_gamma                90
_cell_volume                     4559.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9809
_cell_measurement_theta_min      2.5044
_cell_measurement_theta_max      27.5428

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_F_000             2304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.306
_exptl_crystal_size_min          0.136
_exptl_absorpt_coefficient_mu    1.048
_shelx_estimated_absorpt_T_min   0.739
_shelx_estimated_absorpt_T_max   0.871
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            73421
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.219
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             10490
_reflns_number_gt                9453
_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       'Bruker Instrument Service v2016.1.0.1'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0393P)²+7.7609P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10490
_refine_ls_number_parameters     696
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.002
_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
Ni1A Ni 0.22158(3) 0.65251(2) 0.68799(2) 0.01488(7) Uani 1 1 d . . . . .
N1A N 0.05314(19) 0.67759(5) 0.58129(12) 0.0167(3) Uani 1 1 d . . . . .
C2A C -0.0790(2) 0.65323(6) 0.57052(16) 0.0194(4) Uani 1 1 d . . . . .
H2A H -0.1481 0.6602 0.5106 0.023 Uiso 1 1 calc R U . . .
H2B H -0.1277 0.6575 0.6255 0.023 Uiso 1 1 calc R U . . .
P3A P -0.02875(6) 0.60318(2) 0.56610(4) 0.02102(12) Uani 1 1 d . . . . .
O31A O 0.09971(17) 0.59972(4) 0.65285(10) 0.0198(3) Uani 1 1 d . . . . .
O32A O -0.1591(2) 0.58002(5) 0.57986(14) 0.0348(4) Uani 1 1 d . . . . .
O33A O 0.0171(2) 0.59599(6) 0.47055(12) 0.0374(5) Uani 1 1 d . . . . .
C10A C 0.0304(2) 0.71577(6) 0.62065(16) 0.0203(4) Uani 1 1 d . . . . .
H10A H -0.0258 0.7133 0.6726 0.024 Uiso 1 1 calc R U . . .
H10B H -0.0259 0.7320 0.5692 0.024 Uiso 1 1 calc R U . . .
C11A C 0.1763(2) 0.73393(6) 0.65994(15) 0.0185(4) Uani 1 1 d . . . . .
N12A N 0.28262(19) 0.70976(5) 0.70091(13) 0.0178(3) Uani 1 1 d . . . . .
C13A C 0.4144(2) 0.72405(6) 0.73911(16) 0.0208(4) Uani 1 1 d . . . . .
H13A H 0.4895 0.7070 0.7677 0.025 Uiso 1 1 calc R U . . .
C14A C 0.4451(3) 0.76270(7) 0.73847(16) 0.0245(5) Uani 1 1 d . . . . .
H14A H 0.5390 0.7721 0.7669 0.029 Uiso 1 1 calc R U . . .
C15A C 0.3363(3) 0.78728(6) 0.69568(17) 0.0257(5) Uani 1 1 d . . . . .
H15A H 0.3549 0.8139 0.6936 0.031 Uiso 1 1 calc R U . . .
C16A C 0.1998(3) 0.77294(6) 0.65575(16) 0.0241(5) Uani 1 1 d . . . . .
H16A H 0.1237 0.7895 0.6260 0.029 Uiso 1 1 calc R U . . .
C20A C 0.1043(2) 0.68148(7) 0.48872(15) 0.0212(4) Uani 1 1 d . . . . .
H20A H 0.1149 0.7089 0.4751 0.025 Uiso 1 1 calc R U . . .
H20B H 0.0292 0.6708 0.4362 0.025 Uiso 1 1 calc R U . . .
C21A C 0.2472(2) 0.66174(6) 0.48827(15) 0.0170(4) Uani 1 1 d . . . . .
N22A N 0.3198(2) 0.64658(5) 0.57061(13) 0.0197(4) Uani 1 1 d . . . . .
C23A C 0.4507(2) 0.63026(7) 0.57077(17) 0.0239(5) Uani 1 1 d . . . . .
H23A H 0.5016 0.6190 0.6287 0.029 Uiso 1 1 calc R U . . .
C24A C 0.5135(3) 0.62929(7) 0.49083(18) 0.0263(5) Uani 1 1 d . . . . .
H24A H 0.6060 0.6178 0.4938 0.032 Uiso 1 1 calc R U . . .
C25A C 0.4390(3) 0.64545(7) 0.40600(17) 0.0264(5) Uani 1 1 d . . . . .
H25A H 0.4801 0.6455 0.3499 0.032 Uiso 1 1 calc R U . . .
C26A C 0.3036(3) 0.66157(6) 0.40446(15) 0.0219(4) Uani 1 1 d . . . . .
H26A H 0.2498 0.6724 0.3468 0.026 Uiso 1 1 calc R U . . .
Ni1X Ni 0.29056(3) 0.63242(2) 0.90538(2) 0.01415(7) Uani 1 1 d . . . . .
N1X N 0.46020(18) 0.60608(5) 1.00446(12) 0.0156(3) Uani 1 1 d . . . . .
C2X C 0.4765(2) 0.56661(6) 0.96906(15) 0.0185(4) Uani 1 1 d . . . . .
H2X H 0.5316 0.5510 1.0222 0.022 Uiso 1 1 calc R U . . .
H2Y H 0.5328 0.5674 0.9169 0.022 Uiso 1 1 calc R U . . .
P3X P 0.29820(6) 0.54440(2) 0.92361(4) 0.01677(11) Uani 1 1 d . . . . .
O31X O 0.20991(16) 0.57696(4) 0.86878(11) 0.0186(3) Uani 1 1 d . . . . .
O32X O 0.32793(17) 0.51278(4) 0.85565(11) 0.0224(3) Uani 1 1 d . . . . .
O33X O 0.23356(18) 0.52961(4) 1.00681(11) 0.0238(3) Uani 1 1 d . . . . .
C10X C 0.5898(2) 0.63023(6) 1.00461(17) 0.0208(4) Uani 1 1 d . . . . .
H10X H 0.6317 0.6243 0.9474 0.025 Uiso 1 1 calc R U . . .
H10Y H 0.6647 0.6248 1.0629 0.025 Uiso 1 1 calc R U . . .
C11X C 0.5472(2) 0.67203(6) 1.00304(16) 0.0195(4) Uani 1 1 d . . . . .
N12X N 0.41020(19) 0.68018(5) 0.95809(12) 0.0171(3) Uani 1 1 d . . . . .
C13X C 0.3663(2) 0.71671(6) 0.95318(15) 0.0202(4) Uani 1 1 d . . . . .
H13X H 0.2692 0.7224 0.9221 0.024 Uiso 1 1 calc R U . . .
C14X C 0.4569(3) 0.74638(6) 0.99163(16) 0.0235(4) Uani 1 1 d . . . . .
H14X H 0.4228 0.7720 0.9868 0.028 Uiso 1 1 calc R U . . .
C15X C 0.5977(3) 0.73806(7) 1.03701(18) 0.0284(5) Uani 1 1 d . . . . .
H15X H 0.6625 0.7579 1.0636 0.034 Uiso 1 1 calc R U . . .
C16X C 0.6434(3) 0.70055(7) 1.04326(19) 0.0278(5) Uani 1 1 d . . . . .
H16X H 0.7398 0.6943 1.0748 0.033 Uiso 1 1 calc R U . . .
C20X C 0.4252(2) 0.60615(6) 1.10206(15) 0.0186(4) Uani 1 1 d . . . . .
H20X H 0.4864 0.6255 1.1419 0.022 Uiso 1 1 calc R U . . .
H20Y H 0.4508 0.5810 1.1323 0.022 Uiso 1 1 calc R U . . .
C21X C 0.2678(2) 0.61438(6) 1.10273(15) 0.0174(4) Uani 1 1 d . . . . .
N22X N 0.18763(19) 0.63030(5) 1.02359(13) 0.0175(3) Uani 1 1 d . . . . .
C23X C 0.0491(2) 0.64022(6) 1.02592(18) 0.0235(5) Uani 1 1 d . . . . .
H23X H -0.0098 0.6509 0.9698 0.028 Uiso 1 1 calc R U . . .
C24X C -0.0100(3) 0.63538(7) 1.1072(2) 0.0295(5) Uani 1 1 d . . . . .
H24X H -0.1070 0.6434 1.1072 0.035 Uiso 1 1 calc R U . . .
C25X C 0.0734(3) 0.61881(7) 1.18844(19) 0.0298(5) Uani 1 1 d . . . . .
H25X H 0.0347 0.6152 1.2449 0.036 Uiso 1 1 calc R U . . .
C26X C 0.2141(3) 0.60769(7) 1.18587(17) 0.0248(5) Uani 1 1 d . . . . .
H26X H 0.2731 0.5957 1.2400 0.030 Uiso 1 1 calc R U . . .
Li1 Li 0.0568(4) 0.60038(10) 0.7829(3) 0.0201(7) Uani 1 1 d . . . . .
Li2 Li -0.1898(5) 0.55166(13) 0.6869(4) 0.0400(11) Uani 1 1 d . . . . .
O1W O 0.12150(16) 0.65243(4) 0.80484(10) 0.0156(3) Uani 1 1 d . . . . .
H1W H 0.086(4) 0.6717(10) 0.818(2) 0.040(9) Uiso 1 1 d . . . . .
O2W O 0.39070(16) 0.62988(5) 0.78650(11) 0.0172(3) Uani 1 1 d . . . . .
H2W H 0.387(3) 0.6087(9) 0.774(2) 0.026(8) Uiso 1 1 d . . . . .
O3W O -0.12942(19) 0.58299(5) 0.80656(14) 0.0266(4) Uani 1 1 d . . . . .
H3W H -0.190(4) 0.6001(12) 0.806(3) 0.056(11) Uiso 1 1 d . . . . .
H3V H -0.119(4) 0.5695(12) 0.855(3) 0.060(12) Uiso 1 1 d . . . . .
O4W O -0.0984(3) 0.50119(7) 0.6984(2) 0.0625(8) Uani 1 1 d D . . . .
H4W H -0.144(5) 0.4898(12) 0.651(3) 0.062(12) Uiso 1 1 d . . . . .
H4V H -0.047(4) 0.4903(12) 0.752(2) 0.074 Uiso 1 1 d D U . . .
O5W O -0.3901(2) 0.54019(8) 0.6855(3) 0.0665(9) Uani 1 1 d D . . . .
H5W H -0.475(3) 0.5498(12) 0.668(3) 0.080 Uiso 1 1 d D U . . .
H5V H -0.391(5) 0.5220(15) 0.724(4) 0.089(16) Uiso 1 1 d . . . . .
Cl1P Cl 0.87186(6) 0.74644(2) 0.83262(4) 0.02608(12) Uani 1 1 d . . . . .
O11P O 0.7770(2) 0.71968(6) 0.77400(15) 0.0408(5) Uani 1 1 d . . . . .
O12P O 0.9078(3) 0.77541(7) 0.76703(19) 0.0480(7) Uani 0.861(4) 1 d . . P A 1
O13P O 0.7997(7) 0.7658(2) 0.8987(3) 0.0474(11) Uani 0.861(4) 1 d . . P A 1
O14P O 1.0016(3) 0.72823(8) 0.8779(2) 0.0545(9) Uani 0.861(4) 1 d . . P A 1
O12Q O 0.990(2) 0.7609(5) 0.8039(13) 0.0480(7) Uani 0.139(4) 1 d . . P A 2
O13Q O 0.806(5) 0.7708(16) 0.879(3) 0.0474(11) Uani 0.139(4) 1 d . . P A 2
O14Q O 0.942(2) 0.7206(5) 0.9263(16) 0.0545(9) Uani 0.139(4) 1 d . . P A 2
O6W O 0.6789(2) 0.64090(6) 0.79235(15) 0.0334(4) Uani 1 1 d . . . . .
H6W H 0.703(4) 0.6625(11) 0.793(3) 0.048(11) Uiso 1 1 d . . . . .
H6V H 0.594(4) 0.6398(10) 0.787(3) 0.048(10) Uiso 1 1 d . . . . .
O7W O -0.2065(2) 0.58859(6) 0.31754(15) 0.0356(4) Uani 1 1 d . . . . .
H7W H -0.125(5) 0.5895(11) 0.369(3) 0.065(12) Uiso 1 1 d . . . . .
H7V H -0.175(7) 0.5703(19) 0.277(5) 0.14(2) Uiso 1 1 d . . . . .
O8W O -0.3143(3) 0.65856(7) 0.24914(17) 0.0466(5) Uani 1 1 d . . . . .
H8W H -0.275(3) 0.6377(8) 0.271(2) 0.019(6) Uiso 1 1 d . . . . .
H8V H -0.243(5) 0.6764(13) 0.270(3) 0.078(14) Uiso 1 1 d . . . . .
O9W O 0.5830(2) 0.48753(5) 0.82254(13) 0.0286(4) Uani 1 1 d . . . . .
H9W H 0.647(4) 0.4842(10) 0.873(3) 0.049(10) Uiso 1 1 d . . . . .
H9V H 0.508(4) 0.4959(11) 0.837(3) 0.053(11) Uiso 1 1 d . . . . .
O10W O -0.4933(3) 0.56070(6) 0.33337(17) 0.0467(5) Uani 1 1 d . . . . .
H10W H -0.483(6) 0.5452(15) 0.393(4) 0.099(17) Uiso 1 1 d . . . . .
H10V H -0.522(6) 0.5433(15) 0.280(4) 0.100(17) Uiso 1 1 d . . . . .
O11W O -0.0785(3) 0.54338(6) 0.98155(15) 0.0367(4) Uani 1 1 d D . . . .
H11W H 0.015(2) 0.5372(10) 0.997(2) 0.044 Uiso 1 1 d D U . . .
H11V H -0.135(4) 0.5269(10) 0.971(2) 0.035(9) Uiso 1 1 d . . . . .
O12W O 0.1251(2) 0.45873(6) 0.82215(15) 0.0291(5) Uani 0.819(4) 1 d . . P . .
O12V O 0.2012(11) 0.4418(3) 0.8537(6) 0.0291(5) Uani 0.181(4) 1 d . . P . .
H12W H 0.0927 0.4529 0.8795 0.035 Uiso 1 1 d R U . . .
H12V H 0.2041 0.4762 0.8370 0.035 Uiso 1 1 d R U . . .
Li3A Li -0.2661(13) 0.4815(2) 0.4536(6) 0.074(3) Uani 0.8 1 d . . P B 1
Li3B Li -0.223(6) 0.5068(11) 0.432(2) 0.074(3) Uani 0.2 1 d . . P B 2
O13W O 0.3060(2) 0.54552(6) 0.67106(16) 0.0317(5) Uani 0.8 1 d . . P C 1
H13W H 0.3068 0.5350 0.7277 0.038 Uiso 1 1 d R U . . .
H13V H 0.2362 0.5620 0.6691 0.038 Uiso 1 1 d R U . . .
O13V O -0.1811(10) 0.4787(3) 0.3349(6) 0.0317(5) Uani 0.2 1 d . . P B 2
O14W O 0.2370(3) 0.55440(7) 0.4350(2) 0.0387(6) Uani 0.8 1 d . . P D 1
H14W H 0.1898 0.5675 0.4607 0.046 Uiso 1 1 d R U . . .
H14V H 0.3232 0.5659 0.4285 0.046 Uiso 1 1 d R U . . .
O14V O 0.2198(13) 0.5629(3) 0.3898(9) 0.0387(6) Uani 0.2 1 d . . P E 2
O15W O -0.4479(5) 0.51045(14) 0.4803(4) 0.0690(10) Uiso 0.6 1 d . . P B 1
O15V O -0.3382(10) 0.5278(2) 0.4796(6) 0.0690(10) Uiso 0.4 1 d . . P . .
O16W O -0.1447(9) 0.5156(2) 0.4587(6) 0.0645(18) Uiso 0.4 1 d . . P B 1
O16V O -0.2766(16) 0.5249(4) 0.4670(10) 0.057(3) Uiso 0.2 1 d . . P B 1
O16U O -0.0566(8) 0.5073(2) 0.4541(5) 0.0615(16) Uiso 0.4 1 d . . 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
Ni1A O2W 2.0512(15) . ?
Ni1A O1W 2.0577(15) . ?
Ni1A N22A 2.0641(18) . ?
Ni1A N12A 2.0855(18) . ?
Ni1A N1A 2.1447(17) . ?
Ni1A O31A 2.1800(16) . ?
N1A C10A 1.482(3) . ?
N1A C2A 1.486(3) . ?
N1A C20A 1.489(3) . ?
C2A P3A 1.822(2) . ?
C2A H2A 0.9900 . ?
C2A H2B 0.9900 . ?
P3A O32A 1.5113(19) . ?
P3A O33A 1.5200(18) . ?
P3A O31A 1.5442(15) . ?
O31A Li1 1.962(4) . ?
O32A Li2 1.882(6) . ?
C10A C11A 1.510(3) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A N12A 1.348(3) . ?
C11A C16A 1.389(3) . ?
N12A C13A 1.343(3) . ?
C13A C14A 1.386(3) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.380(3) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.386(4) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
C20A C21A 1.508(3) . ?
C20A H20A 0.9900 . ?
C20A H20B 0.9900 . ?
C21A N22A 1.338(3) . ?
C21A C26A 1.392(3) . ?
N22A C23A 1.353(3) . ?
C23A C24A 1.376(3) . ?
C23A H23A 0.9500 . ?
C24A C25A 1.385(4) . ?
C24A H24A 0.9500 . ?
C25A C26A 1.385(3) . ?
C25A H25A 0.9500 . ?
C26A H26A 0.9500 . ?
Ni1X O1W 2.0327(14) . ?
Ni1X N12X 2.0705(18) . ?
Ni1X O2W 2.0858(15) . ?
Ni1X N22X 2.0928(19) . ?
Ni1X N1X 2.1121(17) . ?
Ni1X O31X 2.1134(15) . ?
N1X C10X 1.480(3) . ?
N1X C20X 1.483(3) . ?
N1X C2X 1.490(2) . ?
C2X P3X 1.839(2) . ?
C2X H2X 0.9900 . ?
C2X H2Y 0.9900 . ?
P3X O33X 1.5190(17) . ?
P3X O31X 1.5282(15) . ?
P3X O32X 1.5296(15) . ?
O31X Li1 1.876(4) . ?
C10X C11X 1.519(3) . ?
C10X H10X 0.9900 . ?
C10X H10Y 0.9900 . ?
C11X N12X 1.345(3) . ?
C11X C16X 1.390(3) . ?
N12X C13X 1.343(3) . ?
C13X C14X 1.384(3) . ?
C13X H13X 0.9500 . ?
C14X C15X 1.379(4) . ?
C14X H14X 0.9500 . ?
C15X C16X 1.381(3) . ?
C15X H15X 0.9500 . ?
C16X H16X 0.9500 . ?
C20X C21X 1.504(3) . ?
C20X H20X 0.9900 . ?
C20X H20Y 0.9900 . ?
C21X N22X 1.341(3) . ?
C21X C26X 1.389(3) . ?
N22X C23X 1.350(3) . ?
C23X C24X 1.384(4) . ?
C23X H23X 0.9500 . ?
C24X C25X 1.384(4) . ?
C24X H24X 0.9500 . ?
C25X C26X 1.382(3) . ?
C25X H25X 0.9500 . ?
C26X H26X 0.9500 . ?
Li1 O1W 1.929(4) . ?
Li1 O3W 1.939(4) . ?
Li2 O5W 1.915(6) . ?
Li2 O4W 1.958(5) . ?
Li2 O3W 2.005(6) . ?
Li2 H4W 2.29(4) . ?
Li2 H5V 2.31(5) . ?
O1W H1W 0.79(3) . ?
O2W H2W 0.76(3) . ?
O3W H3W 0.83(4) . ?
O3W H3V 0.82(4) . ?
O4W H4W 0.82(4) . ?
O4W H4V 0.903(19) . ?
O5W H5W 0.850(19) . ?
O5W H5V 0.84(5) . ?
Cl1P O13Q 1.30(5) . ?
Cl1P O12Q 1.355(17) . ?
Cl1P O14P 1.410(2) . ?
Cl1P O13P 1.430(6) . ?
Cl1P O11P 1.4375(19) . ?
Cl1P O12P 1.460(2) . ?
Cl1P O14Q 1.63(2) . ?
O6W H6W 0.79(4) . ?
O6W H6V 0.78(4) . ?
O7W H7W 0.95(4) . ?
O7W H7V 0.95(7) . ?
O8W H8W 0.85(3) . ?
O8W H8V 0.92(5) . ?
O9W H9W 0.85(4) . ?
O9W H9V 0.82(4) . ?
O10W H10W 0.99(5) . ?
O10W H10V 0.97(5) . ?
O11W H11W 0.883(18) . ?
O11W H11V 0.78(3) . ?
O12W O12V 0.965(10) . ?
O12W H12W 0.9435 . ?
O12W H12V 0.9515 . ?
O12V H12W 1.2095 . ?
O12V H12V 1.2296 . ?
Li3A O16V 1.541(16) . ?
Li3A O16W 1.644(14) . ?
Li3A O15V 1.824(12) . ?
Li3A O13W 1.973(8) 3_566 ?
Li3A O14W 1.993(9) 3_566 ?
Li3A O15W 2.081(11) . ?
Li3A O16U 2.161(14) . ?
Li3B O16U 1.52(6) . ?
Li3B O15V 1.57(5) . ?
Li3B O13V 1.79(4) . ?
O13W Li3A 1.973(8) 3_566 ?
O13W H13W 0.8829 . ?
O13W H13V 0.8674 . ?
O14W Li3A 1.993(9) 3_566 ?
O14W H14W 0.7757 . ?
O14W H14V 0.9240 . ?
O14V H14W 1.1062 . ?
O14V H14V 1.0197 . ?

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
O2W Ni1A O1W 82.31(6) . . ?
O2W Ni1A N22A 95.82(7) . . ?
O1W Ni1A N22A 174.13(7) . . ?
O2W Ni1A N12A 98.72(7) . . ?
O1W Ni1A N12A 95.25(6) . . ?
N22A Ni1A N12A 90.54(7) . . ?
O2W Ni1A N1A 176.95(7) . . ?
O1W Ni1A N1A 100.27(6) . . ?
N22A Ni1A N1A 81.77(7) . . ?
N12A Ni1A N1A 79.48(7) . . ?
O2W Ni1A O31A 97.20(6) . . ?
O1W Ni1A O31A 83.16(6) . . ?
N22A Ni1A O31A 91.57(7) . . ?
N12A Ni1A O31A 163.64(6) . . ?
N1A Ni1A O31A 84.77(6) . . ?
C10A N1A C2A 112.27(16) . . ?
C10A N1A C20A 110.13(17) . . ?
C2A N1A C20A 111.67(17) . . ?
C10A N1A Ni1A 104.25(12) . . ?
C2A N1A Ni1A 108.51(12) . . ?
C20A N1A Ni1A 109.72(12) . . ?
N1A C2A P3A 110.00(14) . . ?
N1A C2A H2A 109.7 . . ?
P3A C2A H2A 109.7 . . ?
N1A C2A H2B 109.7 . . ?
P3A C2A H2B 109.7 . . ?
H2A C2A H2B 108.2 . . ?
O32A P3A O33A 113.85(12) . . ?
O32A P3A O31A 112.15(10) . . ?
O33A P3A O31A 112.46(10) . . ?
O32A P3A C2A 107.01(11) . . ?
O33A P3A C2A 108.12(11) . . ?
O31A P3A C2A 102.36(9) . . ?
P3A O31A Li1 118.26(14) . . ?
P3A O31A Ni1A 113.88(8) . . ?
Li1 O31A Ni1A 88.36(12) . . ?
P3A O32A Li2 130.12(19) . . ?
N1A C10A C11A 109.40(17) . . ?
N1A C10A H10A 109.8 . . ?
C11A C10A H10A 109.8 . . ?
N1A C10A H10B 109.8 . . ?
C11A C10A H10B 109.8 . . ?
H10A C10A H10B 108.2 . . ?
N12A C11A C16A 121.9(2) . . ?
N12A C11A C10A 115.49(18) . . ?
C16A C11A C10A 122.6(2) . . ?
C13A N12A C11A 118.68(19) . . ?
C13A N12A Ni1A 127.51(15) . . ?
C11A N12A Ni1A 113.68(14) . . ?
N12A C13A C14A 122.5(2) . . ?
N12A C13A H13A 118.7 . . ?
C14A C13A H13A 118.7 . . ?
C15A C14A C13A 118.5(2) . . ?
C15A C14A H14A 120.7 . . ?
C13A C14A H14A 120.7 . . ?
C14A C15A C16A 119.6(2) . . ?
C14A C15A H15A 120.2 . . ?
C16A C15A H15A 120.2 . . ?
C15A C16A C11A 118.8(2) . . ?
C15A C16A H16A 120.6 . . ?
C11A C16A H16A 120.6 . . ?
N1A C20A C21A 113.77(17) . . ?
N1A C20A H20A 108.8 . . ?
C21A C20A H20A 108.8 . . ?
N1A C20A H20B 108.8 . . ?
C21A C20A H20B 108.8 . . ?
H20A C20A H20B 107.7 . . ?
N22A C21A C26A 121.9(2) . . ?
N22A C21A C20A 118.45(18) . . ?
C26A C21A C20A 119.55(19) . . ?
C21A N22A C23A 118.22(19) . . ?
C21A N22A Ni1A 115.58(14) . . ?
C23A N22A Ni1A 126.16(15) . . ?
N22A C23A C24A 123.0(2) . . ?
N22A C23A H23A 118.5 . . ?
C24A C23A H23A 118.5 . . ?
C23A C24A C25A 118.7(2) . . ?
C23A C24A H24A 120.7 . . ?
C25A C24A H24A 120.7 . . ?
C26A C25A C24A 118.9(2) . . ?
C26A C25A H25A 120.6 . . ?
C24A C25A H25A 120.6 . . ?
C25A C26A C21A 119.3(2) . . ?
C25A C26A H26A 120.3 . . ?
C21A C26A H26A 120.3 . . ?
O1W Ni1X N12X 105.29(6) . . ?
O1W Ni1X O2W 82.06(6) . . ?
N12X Ni1X O2W 91.58(7) . . ?
O1W Ni1X N22X 98.87(6) . . ?
N12X Ni1X N22X 92.44(7) . . ?
O2W Ni1X N22X 175.47(7) . . ?
O1W Ni1X N1X 174.24(6) . . ?
N12X Ni1X N1X 80.35(7) . . ?
O2W Ni1X N1X 96.78(6) . . ?
N22X Ni1X N1X 81.85(7) . . ?
O1W Ni1X O31X 87.44(6) . . ?
N12X Ni1X O31X 167.03(6) . . ?
O2W Ni1X O31X 87.64(6) . . ?
N22X Ni1X O31X 87.97(6) . . ?
N1X Ni1X O31X 86.88(6) . . ?
C10X N1X C20X 109.33(16) . . ?
C10X N1X C2X 113.14(16) . . ?
C20X N1X C2X 111.82(16) . . ?
C10X N1X Ni1X 105.03(12) . . ?
C20X N1X Ni1X 110.00(12) . . ?
C2X N1X Ni1X 107.25(12) . . ?
N1X C2X P3X 111.37(13) . . ?
N1X C2X H2X 109.4 . . ?
P3X C2X H2X 109.4 . . ?
N1X C2X H2Y 109.4 . . ?
P3X C2X H2Y 109.4 . . ?
H2X C2X H2Y 108.0 . . ?
O33X P3X O31X 112.97(9) . . ?
O33X P3X O32X 113.03(9) . . ?
O31X P3X O32X 111.69(9) . . ?
O33X P3X C2X 110.32(10) . . ?
O31X P3X C2X 102.92(9) . . ?
O32X P3X C2X 105.13(9) . . ?
P3X O31X Li1 157.46(15) . . ?
P3X O31X Ni1X 115.59(8) . . ?
Li1 O31X Ni1X 86.91(13) . . ?
N1X C10X C11X 109.82(17) . . ?
N1X C10X H10X 109.7 . . ?
C11X C10X H10X 109.7 . . ?
N1X C10X H10Y 109.7 . . ?
C11X C10X H10Y 109.7 . . ?
H10X C10X H10Y 108.2 . . ?
N12X C11X C16X 121.4(2) . . ?
N12X C11X C10X 115.82(18) . . ?
C16X C11X C10X 122.8(2) . . ?
C13X N12X C11X 118.73(19) . . ?
C13X N12X Ni1X 127.95(15) . . ?
C11X N12X Ni1X 113.31(14) . . ?
N12X C13X C14X 122.6(2) . . ?
N12X C13X H13X 118.7 . . ?
C14X C13X H13X 118.7 . . ?
C15X C14X C13X 118.6(2) . . ?
C15X C14X H14X 120.7 . . ?
C13X C14X H14X 120.7 . . ?
C14X C15X C16X 119.1(2) . . ?
C14X C15X H15X 120.4 . . ?
C16X C15X H15X 120.4 . . ?
C15X C16X C11X 119.5(2) . . ?
C15X C16X H16X 120.3 . . ?
C11X C16X H16X 120.3 . . ?
N1X C20X C21X 113.88(16) . . ?
N1X C20X H20X 108.8 . . ?
C21X C20X H20X 108.8 . . ?
N1X C20X H20Y 108.8 . . ?
C21X C20X H20Y 108.8 . . ?
H20X C20X H20Y 107.7 . . ?
N22X C21X C26X 122.8(2) . . ?
N22X C21X C20X 117.47(19) . . ?
C26X C21X C20X 119.57(19) . . ?
C21X N22X C23X 117.9(2) . . ?
C21X N22X Ni1X 114.41(14) . . ?
C23X N22X Ni1X 127.46(16) . . ?
N22X C23X C24X 122.3(2) . . ?
N22X C23X H23X 118.9 . . ?
C24X C23X H23X 118.9 . . ?
C23X C24X C25X 119.3(2) . . ?
C23X C24X H24X 120.3 . . ?
C25X C24X H24X 120.3 . . ?
C26X C25X C24X 118.7(2) . . ?
C26X C25X H25X 120.6 . . ?
C24X C25X H25X 120.6 . . ?
C25X C26X C21X 118.9(2) . . ?
C25X C26X H26X 120.6 . . ?
C21X C26X H26X 120.6 . . ?
O31X Li1 O1W 97.74(17) . . ?
O31X Li1 O3W 110.4(2) . . ?
O1W Li1 O3W 122.3(2) . . ?
O31X Li1 O31A 109.32(19) . . ?
O1W Li1 O31A 92.64(17) . . ?
O3W Li1 O31A 121.2(2) . . ?
O32A Li2 O5W 114.1(3) . . ?
O32A Li2 O4W 114.3(3) . . ?
O5W Li2 O4W 102.8(2) . . ?
O32A Li2 O3W 109.2(2) . . ?
O5W Li2 O3W 103.6(3) . . ?
O4W Li2 O3W 112.3(3) . . ?
Li1 O1W Ni1X 87.83(12) . . ?
Li1 O1W Ni1A 92.89(13) . . ?
Ni1X O1W Ni1A 98.51(6) . . ?
Li1 O1W H1W 135(2) . . ?
Ni1X O1W H1W 116(2) . . ?
Ni1A O1W H1W 118(2) . . ?
Ni1A O2W Ni1X 97.02(6) . . ?
Ni1A O2W H2W 103(2) . . ?
Ni1X O2W H2W 103(2) . . ?
Li1 O3W Li2 98.0(2) . . ?
Li1 O3W H3W 114(3) . . ?
Li2 O3W H3W 108(3) . . ?
Li1 O3W H3V 111(3) . . ?
Li2 O3W H3V 111(3) . . ?
H3W O3W H3V 113(4) . . ?
Li2 O4W H4W 103(3) . . ?
Li2 O4W H4V 127(3) . . ?
H4W O4W H4V 126(4) . . ?
Li2 O5W H5W 141(3) . . ?
Li2 O5W H5V 107(3) . . ?
H5W O5W H5V 111(4) . . ?
O13Q Cl1P O12Q 114(2) . . ?
O14P Cl1P O13P 113.2(3) . . ?
O13Q Cl1P O11P 115(2) . . ?
O12Q Cl1P O11P 121.4(7) . . ?
O14P Cl1P O11P 110.18(14) . . ?
O13P Cl1P O11P 111.7(3) . . ?
O14P Cl1P O12P 108.5(2) . . ?
O13P Cl1P O12P 106.6(3) . . ?
O11P Cl1P O12P 106.32(15) . . ?
O13Q Cl1P O14Q 96(2) . . ?
O12Q Cl1P O14Q 103.2(11) . . ?
O11P Cl1P O14Q 102.2(6) . . ?
H6W O6W H6V 110(4) . . ?
H7W O7W H7V 101(4) . . ?
H8W O8W H8V 104(3) . . ?
H9W O9W H9V 109(3) . . ?
H10W O10W H10V 106(4) . . ?
H11W O11W H11V 118(3) . . ?
O12V O12W H12W 78.6 . . ?
O12V O12W H12V 79.8 . . ?
H12W O12W H12V 108.6 . . ?
O12W O12V H12W 49.9 . . ?
O12W O12V H12V 49.6 . . ?
H12W O12V H12V 78.2 . . ?
O16V Li3A O13W 125.4(7) . 3_566 ?
O16W Li3A O13W 113.3(6) . 3_566 ?
O15V Li3A O13W 126.6(5) . 3_566 ?
O16V Li3A O14W 121.9(7) . 3_566 ?
O16W Li3A O14W 116.1(6) . 3_566 ?
O15V Li3A O14W 113.6(5) . 3_566 ?
O13W Li3A O14W 112.2(4) 3_566 3_566 ?
Li3A O13W H13W 125.4 3_566 . ?
Li3A O13W H13V 106.4 3_566 . ?
H13W O13W H13V 100.3 . . ?
Li3A O14W H14W 90.2 3_566 . ?
Li3A O14W H14V 111.7 3_566 . ?
H14W O14W H14V 112.3 . . ?
H14W O14V H14V 83.3 . . ?

_refine_diff_density_max         1.981
_refine_diff_density_min         -0.750
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_cudpabpin_ii
_database_code_depnum_ccdc_archive 'CCDC 1815205'
_audit_update_record             
;
2018-01-07 deposited with the CCDC.
2018-03-26 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         'C14 H21 Cl Cu Li N3 O6 P2, 3(H2 O)'
_chemical_formula_sum            'C14 H27 Cl Cu Li N3 O9 P2'
_chemical_formula_weight         549.25

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'
Li Li -0.0003 0.0001 '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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2892(4)
_cell_length_b                   8.6425(4)
_cell_length_c                   16.9266(8)
_cell_angle_alpha                80.3194(17)
_cell_angle_beta                 83.4676(17)
_cell_angle_gamma                67.5168(15)
_cell_volume                     1102.86(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9862
_cell_measurement_theta_min      2.6633
_cell_measurement_theta_max      27.5185

_exptl_crystal_description       prism
_exptl_crystal_colour            'light blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_F_000             566
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.307
_shelx_estimated_absorpt_T_min   0.694
_shelx_estimated_absorpt_T_max   0.914
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            29687
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.445
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5074
_reflns_number_gt                4637
_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       'Bruker Instrument Service v2016.1.0.1'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0268P)²+1.1124P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5074
_refine_ls_number_parameters     318
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0632
_refine_ls_wR_factor_gt          0.0613
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
Cu1 Cu 0.58671(3) 0.45048(2) 0.38431(2) 0.00948(6) Uani 1 1 d . . . . .
Cl1 Cl 0.70286(5) 0.29312(5) 0.50030(2) 0.01615(9) Uani 1 1 d . . . . .
N1 N 0.47093(17) 0.61202(17) 0.28316(8) 0.0100(3) Uani 1 1 d . . . . .
C2 C 0.5918(2) 0.5670(2) 0.21063(10) 0.0115(3) Uani 1 1 d . . . . .
H21 H 0.6830 0.6157 0.2084 0.014 Uiso 1 1 calc R U . . .
H22 H 0.5252 0.6162 0.1616 0.014 Uiso 1 1 calc R U . . .
P3 P 0.69562(5) 0.33764(5) 0.21354(3) 0.01021(9) Uani 1 1 d . . . . .
O31 O 0.75499(15) 0.27252(14) 0.29772(7) 0.0137(2) Uani 1 1 d . . . . .
O32 O 0.57153(15) 0.27421(15) 0.18262(7) 0.0146(2) Uani 1 1 d . . . . .
C4 C 0.8881(2) 0.2991(2) 0.14535(10) 0.0138(3) Uani 1 1 d . . . . .
H41 H 0.9583 0.3611 0.1582 0.017 Uiso 1 1 calc R U . . .
H42 H 0.8517 0.3417 0.0896 0.017 Uiso 1 1 calc R U . . .
P5 P 1.02061(6) 0.07489(6) 0.15322(3) 0.01548(10) Uani 1 1 d . . . . .
H51P H 1.0643 0.0358 0.2287 0.019 Uiso 1 1 d R U . . .
O51 O 0.90697(17) -0.02062(16) 0.14546(9) 0.0228(3) Uani 1 1 d . . . . .
O52 O 1.18136(17) 0.04642(17) 0.09728(9) 0.0222(3) Uani 1 1 d . . . . .
C10 C 0.2993(2) 0.6000(2) 0.27589(11) 0.0147(3) Uani 1 1 d . . . . .
H101 H 0.2805 0.6069 0.2185 0.018 Uiso 1 1 calc R U . . .
H102 H 0.2050 0.6968 0.2973 0.018 Uiso 1 1 calc R U . . .
C11 C 0.2890(2) 0.4374(2) 0.32066(10) 0.0117(3) Uani 1 1 d . . . . .
N12 N 0.40097(18) 0.35713(17) 0.37924(8) 0.0107(3) Uani 1 1 d . . . . .
C13 C 0.3903(2) 0.2163(2) 0.42342(10) 0.0138(3) Uani 1 1 d . . . . .
H131 H 0.4709 0.1584 0.4641 0.017 Uiso 1 1 calc R U . . .
C14 C 0.2662(2) 0.1527(2) 0.41173(11) 0.0164(3) Uani 1 1 d . . . . .
H141 H 0.2613 0.0533 0.4440 0.020 Uiso 1 1 calc R U . . .
C15 C 0.1490(2) 0.2367(2) 0.35215(11) 0.0182(4) Uani 1 1 d . . . . .
H151 H 0.0616 0.1964 0.3434 0.022 Uiso 1 1 calc R U . . .
C16 C 0.1614(2) 0.3801(2) 0.30561(11) 0.0167(3) Uani 1 1 d . . . . .
H161 H 0.0838 0.4386 0.2639 0.020 Uiso 1 1 calc R U . . .
C20 C 0.4506(2) 0.7834(2) 0.29811(10) 0.0118(3) Uani 1 1 d . . . . .
H201 H 0.3481 0.8277 0.3356 0.014 Uiso 1 1 calc R U . . .
H202 H 0.4316 0.8617 0.2471 0.014 Uiso 1 1 calc R U . . .
C21 C 0.6139(2) 0.7710(2) 0.33371(10) 0.0110(3) Uani 1 1 d . . . . .
N22 N 0.69627(18) 0.62286(17) 0.37959(8) 0.0107(3) Uani 1 1 d . . . . .
C23 C 0.8393(2) 0.6045(2) 0.41607(10) 0.0136(3) Uani 1 1 d . . . . .
H231 H 0.8987 0.5000 0.4477 0.016 Uiso 1 1 calc R U . . .
C24 C 0.9033(2) 0.7332(2) 0.40909(11) 0.0163(3) Uani 1 1 d . . . . .
H241 H 1.0040 0.7174 0.4360 0.020 Uiso 1 1 calc R U . . .
C25 C 0.8181(2) 0.8850(2) 0.36230(11) 0.0176(4) Uani 1 1 d . . . . .
H251 H 0.8593 0.9750 0.3570 0.021 Uiso 1 1 calc R U . . .
C26 C 0.6718(2) 0.9042(2) 0.32331(10) 0.0151(3) Uani 1 1 d . . . . .
H261 H 0.6125 1.0065 0.2902 0.018 Uiso 1 1 calc R U . . .
Li1 Li 0.6654(4) 0.0997(4) 0.1119(2) 0.0200(6) Uani 1 1 d . . . . .
O1W O 0.53757(19) -0.04409(18) 0.11239(9) 0.0206(3) Uani 1 1 d . . . . .
H11W H 0.596(5) -0.123(5) 0.077(2) 0.080(12) Uiso 1 1 d . . . . .
H12W H 0.429(4) -0.006(4) 0.1081(19) 0.055(9) Uiso 1 1 d . . . . .
O2W O 0.6790(2) 0.2063(2) 0.00176(9) 0.0313(4) Uani 1 1 d . . . . .
H21W H 0.735(4) 0.139(4) -0.034(2) 0.062(10) Uiso 1 1 d . . . . .
H22W H 0.673(4) 0.311(4) -0.0224(19) 0.056(9) Uiso 1 1 d . . . . .
O3W O 0.3156(2) 0.48064(18) 0.07594(10) 0.0247(3) Uani 1 1 d D . . . .
H31W H 0.379(4) 0.423(4) 0.111(2) 0.056(10) Uiso 1 1 d . . . . .
H32W H 0.296(4) 0.414(4) 0.048(2) 0.067 Uiso 1 1 d D U . . .
O4W O 0.76021(19) 0.71404(19) 0.01837(9) 0.0236(3) Uani 1 1 d D . . . .
H41W H 0.788(4) 0.783(4) -0.0210(19) 0.048(8) Uiso 1 1 d . . . . .
H42W H 0.842(4) 0.674(4) 0.0545(18) 0.057 Uiso 1 1 d D U . . .
O5W O 0.98238(19) 0.64620(18) 0.13983(9) 0.0233(3) Uani 1 1 d D . . . .
H51W H 0.960(3) 0.742(3) 0.1450(14) 0.023(6) Uiso 1 1 d . . . . .
H52W H 1.088(3) 0.602(3) 0.1194(15) 0.028 Uiso 1 1 d D 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
Cu1 N22 2.0072(14) . ?
Cu1 N12 2.0080(14) . ?
Cu1 N1 2.0848(14) . ?
Cu1 O31 2.2609(12) . ?
Cu1 Cl1 2.2719(4) . ?
N1 C10 1.486(2) . ?
N1 C20 1.487(2) . ?
N1 C2 1.498(2) . ?
C2 P3 1.8290(16) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
P3 O31 1.5056(12) . ?
P3 O32 1.5108(12) . ?
P3 C4 1.8143(17) . ?
O32 Li1 1.952(3) . ?
C4 P5 1.8160(17) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
P5 O51 1.4985(14) . ?
P5 O52 1.5077(13) . ?
P5 H51P 1.3211 . ?
O51 Li1 1.970(4) . ?
C10 C11 1.509(2) . ?
C10 H101 0.9900 . ?
C10 H102 0.9900 . ?
C11 N12 1.346(2) . ?
C11 C16 1.390(2) . ?
N12 C13 1.345(2) . ?
C13 C14 1.384(2) . ?
C13 H131 0.9500 . ?
C14 C15 1.387(3) . ?
C14 H141 0.9500 . ?
C15 C16 1.385(3) . ?
C15 H151 0.9500 . ?
C16 H161 0.9500 . ?
C20 C21 1.504(2) . ?
C20 H201 0.9900 . ?
C20 H202 0.9900 . ?
C21 N22 1.351(2) . ?
C21 C26 1.386(2) . ?
N22 C23 1.343(2) . ?
C23 C24 1.387(2) . ?
C23 H231 0.9500 . ?
C24 C25 1.384(3) . ?
C24 H241 0.9500 . ?
C25 C26 1.387(3) . ?
C25 H251 0.9500 . ?
C26 H261 0.9500 . ?
Li1 O1W 1.915(3) . ?
Li1 O2W 1.948(4) . ?
O1W H11W 0.93(4) . ?
O1W H12W 0.84(3) . ?
O2W H21W 0.88(4) . ?
O2W H22W 0.91(3) . ?
O3W H31W 0.81(3) . ?
O3W H32W 0.87(3) . ?
O4W H41W 0.89(3) . ?
O4W H42W 0.89(3) . ?
O5W H51W 0.79(3) . ?
O5W H52W 0.87(2) . ?

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
N22 Cu1 N12 158.74(6) . . ?
N22 Cu1 N1 80.83(5) . . ?
N12 Cu1 N1 83.22(5) . . ?
N22 Cu1 O31 104.78(5) . . ?
N12 Cu1 O31 88.00(5) . . ?
N1 Cu1 O31 86.11(5) . . ?
N22 Cu1 Cl1 96.65(4) . . ?
N12 Cu1 Cl1 98.19(4) . . ?
N1 Cu1 Cl1 175.24(4) . . ?
O31 Cu1 Cl1 98.47(3) . . ?
C10 N1 C20 111.72(13) . . ?
C10 N1 C2 112.40(13) . . ?
C20 N1 C2 109.20(12) . . ?
C10 N1 Cu1 108.86(10) . . ?
C20 N1 Cu1 104.98(10) . . ?
C2 N1 Cu1 109.40(10) . . ?
N1 C2 P3 110.87(11) . . ?
N1 C2 H21 109.5 . . ?
P3 C2 H21 109.5 . . ?
N1 C2 H22 109.5 . . ?
P3 C2 H22 109.5 . . ?
H21 C2 H22 108.1 . . ?
O31 P3 O32 119.01(7) . . ?
O31 P3 C4 108.23(8) . . ?
O32 P3 C4 108.76(7) . . ?
O31 P3 C2 105.02(7) . . ?
O32 P3 C2 108.75(7) . . ?
C4 P3 C2 106.36(8) . . ?
P3 O31 Cu1 110.85(6) . . ?
P3 O32 Li1 118.78(12) . . ?
P3 C4 P5 110.82(9) . . ?
P3 C4 H41 109.5 . . ?
P5 C4 H41 109.5 . . ?
P3 C4 H42 109.5 . . ?
P5 C4 H42 109.5 . . ?
H41 C4 H42 108.1 . . ?
O51 P5 O52 117.45(8) . . ?
O51 P5 C4 109.13(8) . . ?
O52 P5 C4 109.83(8) . . ?
O51 P5 H51P 105.7 . . ?
O52 P5 H51P 110.4 . . ?
C4 P5 H51P 103.3 . . ?
P5 O51 Li1 120.69(12) . . ?
N1 C10 C11 111.94(13) . . ?
N1 C10 H101 109.2 . . ?
C11 C10 H101 109.2 . . ?
N1 C10 H102 109.2 . . ?
C11 C10 H102 109.2 . . ?
H101 C10 H102 107.9 . . ?
N12 C11 C16 121.78(16) . . ?
N12 C11 C10 116.86(14) . . ?
C16 C11 C10 121.21(15) . . ?
C13 N12 C11 118.84(14) . . ?
C13 N12 Cu1 125.89(12) . . ?
C11 N12 Cu1 114.97(11) . . ?
N12 C13 C14 122.30(16) . . ?
N12 C13 H131 118.8 . . ?
C14 C13 H131 118.8 . . ?
C13 C14 C15 118.91(16) . . ?
C13 C14 H141 120.5 . . ?
C15 C14 H141 120.5 . . ?
C16 C15 C14 118.96(16) . . ?
C16 C15 H151 120.5 . . ?
C14 C15 H151 120.5 . . ?
C15 C16 C11 119.18(16) . . ?
C15 C16 H161 120.4 . . ?
C11 C16 H161 120.4 . . ?
N1 C20 C21 108.55(13) . . ?
N1 C20 H201 110.0 . . ?
C21 C20 H201 110.0 . . ?
N1 C20 H202 110.0 . . ?
C21 C20 H202 110.0 . . ?
H201 C20 H202 108.4 . . ?
N22 C21 C26 122.30(15) . . ?
N22 C21 C20 115.08(14) . . ?
C26 C21 C20 122.56(15) . . ?
C23 N22 C21 118.61(14) . . ?
C23 N22 Cu1 127.01(11) . . ?
C21 N22 Cu1 114.38(11) . . ?
N22 C23 C24 122.16(16) . . ?
N22 C23 H231 118.9 . . ?
C24 C23 H231 118.9 . . ?
C25 C24 C23 119.02(16) . . ?
C25 C24 H241 120.5 . . ?
C23 C24 H241 120.5 . . ?
C24 C25 C26 119.25(16) . . ?
C24 C25 H251 120.4 . . ?
C26 C25 H251 120.4 . . ?
C21 C26 C25 118.65(16) . . ?
C21 C26 H261 120.7 . . ?
C25 C26 H261 120.7 . . ?
O1W Li1 O2W 107.01(17) . . ?
O1W Li1 O32 116.60(17) . . ?
O2W Li1 O32 109.12(16) . . ?
O1W Li1 O51 114.13(17) . . ?
O2W Li1 O51 107.18(17) . . ?
O32 Li1 O51 102.39(16) . . ?
Li1 O1W H11W 109(2) . . ?
Li1 O1W H12W 123(2) . . ?
H11W O1W H12W 111(3) . . ?
Li1 O2W H21W 117(2) . . ?
Li1 O2W H22W 136(2) . . ?
H21W O2W H22W 104(3) . . ?
H31W O3W H32W 109(3) . . ?
H41W O4W H42W 110(3) . . ?
H51W O5W H52W 111(2) . . ?

_refine_diff_density_max         0.687
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_vh087_sqd
_database_code_depnum_ccdc_archive 'CCDC 1815213'
_audit_update_record             
;
2018-01-07 deposited with the CCDC.
2018-03-26 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         'C30 H34 N8 Ni2 O4 P2 S2, C3 H8 O'
_chemical_formula_sum            'C33 H42 N8 Ni2 O5 P2 S2'
_chemical_formula_weight         814.13

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'
Ni Ni 0.3393 1.1124 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.4639(4)
_cell_length_b                   10.6323(4)
_cell_length_c                   15.2654(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.2710(10)
_cell_angle_gamma                90
_cell_volume                     1976.75(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9188
_cell_measurement_theta_min      2.3523
_cell_measurement_theta_max      25.9437

_exptl_crystal_description       plate
_exptl_crystal_colour            'light blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.194
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.035
_exptl_absorpt_coefficient_mu    1.181
_shelx_estimated_absorpt_T_min   0.803
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            20019
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.352
_diffrn_reflns_theta_max         26.012
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3880
_reflns_number_gt                3374
_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.
;

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.500 150 34 'C3 H8 O'
2 0.500 0.500 1.000 150 34 'C3 H8 O'
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

_computing_data_collection       'Bruker Instrument Service v2016.1.0.1'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0315P)²+1.3426P] 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         3880
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0683
_refine_ls_wR_factor_gt          0.0661
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_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
Ni1 Ni 0.14421(2) 0.41407(2) 0.63310(2) 0.01496(8) Uani 1 1 d . . . . .
N1T N 0.17079(14) 0.22609(15) 0.63446(10) 0.0231(4) Uani 1 1 d . . . . .
C2T C 0.1928(5) 0.1258(6) 0.6614(4) 0.0222(10) Uani 0.738(2) 1 d . . P A 1
S3T S 0.22112(14) -0.01794(9) 0.69618(8) 0.0563(4) Uani 0.738(2) 1 d . . P A 1
C2U C 0.2142(18) 0.130(2) 0.6463(13) 0.0222(10) Uani 0.262(2) 1 d . . P A 2
S3U S 0.2783(4) -0.0045(3) 0.6716(2) 0.0563(4) Uani 0.262(2) 1 d . . P A 2
N1 N 0.13957(13) 0.61363(14) 0.65109(10) 0.0180(3) Uani 1 1 d . . . . .
C2 C 0.09566(16) 0.67627(17) 0.56353(12) 0.0203(4) Uani 1 1 d . . . . .
H21 H 0.1313 0.7594 0.5632 0.024 Uiso 1 1 calc R U . . .
H22 H 0.0159 0.6905 0.5573 0.024 Uiso 1 1 calc R U . . .
P3 P 0.11821(4) 0.58441(4) 0.46702(3) 0.01706(11) Uani 1 1 d . . . . .
O31 O 0.13503(11) 0.44933(12) 0.49835(8) 0.0198(3) Uani 1 1 d . . . . .
O32 O 0.02443(10) 0.61175(12) 0.38928(8) 0.0195(3) Uani 1 1 d . . . . .
C4 C 0.24126(17) 0.6405(2) 0.43619(14) 0.0287(5) Uani 1 1 d . . . . .
H41 H 0.2496 0.5996 0.3805 0.034 Uiso 1 1 calc R U . . .
H42 H 0.3049 0.6207 0.4840 0.034 Uiso 1 1 calc R U . . .
H43 H 0.2363 0.7318 0.4272 0.034 Uiso 1 1 calc R U . . .
C10 C 0.06709(17) 0.63071(18) 0.71561(12) 0.0219(4) Uani 1 1 d . . . . .
H101 H -0.0105 0.6186 0.6848 0.026 Uiso 1 1 calc R U . . .
H102 H 0.0753 0.7170 0.7404 0.026 Uiso 1 1 calc R U . . .
C11 C 0.09810(16) 0.53603(17) 0.79035(12) 0.0188(4) Uani 1 1 d . . . . .
N12 N 0.14038(13) 0.42686(14) 0.76831(10) 0.0177(3) Uani 1 1 d . . . . .
C13 C 0.16839(15) 0.33802(18) 0.83169(12) 0.0198(4) Uani 1 1 d . . . . .
H131 H 0.1982 0.2611 0.8161 0.024 Uiso 1 1 calc R U . . .
C14 C 0.15554(16) 0.35418(19) 0.91826(13) 0.0229(4) Uani 1 1 d . . . . .
H141 H 0.1763 0.2898 0.9617 0.027 Uiso 1 1 calc R U . . .
C15 C 0.11161(17) 0.4665(2) 0.94068(13) 0.0265(4) Uani 1 1 d . . . . .
H151 H 0.1017 0.4799 1.0000 0.032 Uiso 1 1 calc R U . . .
C16 C 0.08232(17) 0.55870(19) 0.87628(13) 0.0244(4) Uani 1 1 d . . . . .
H161 H 0.0520 0.6361 0.8905 0.029 Uiso 1 1 calc R U . . .
C20 C 0.25309(17) 0.65508(18) 0.69205(14) 0.0260(4) Uani 1 1 d . . . . .
H201 H 0.2624 0.6553 0.7581 0.031 Uiso 1 1 calc R U . . .
H202 H 0.2633 0.7424 0.6728 0.031 Uiso 1 1 calc R U . . .
C21 C 0.33968(17) 0.5733(2) 0.66724(14) 0.0278(5) Uani 1 1 d . . . . .
N22 N 0.31264(13) 0.45250(16) 0.65031(11) 0.0238(4) Uani 1 1 d . . . . .
C23 C 0.38837(18) 0.3741(2) 0.63021(17) 0.0388(6) Uani 1 1 d . . . . .
H231 H 0.3693 0.2885 0.6178 0.047 Uiso 1 1 calc R U . . .
C24 C 0.4925(2) 0.4134(3) 0.6270(2) 0.0597(8) Uani 1 1 d . . . . .
H241 H 0.5447 0.3554 0.6135 0.072 Uiso 1 1 calc R U . . .
C25 C 0.5203(2) 0.5378(3) 0.6435(2) 0.0632(9) Uani 1 1 d . . . . .
H251 H 0.5915 0.5670 0.6408 0.076 Uiso 1 1 calc R U . . .
C26 C 0.4433(2) 0.6190(3) 0.66391(19) 0.0461(7) Uani 1 1 d . . . . .
H261 H 0.4607 0.7052 0.6756 0.055 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
Ni1 N1T 2.0252(16) . ?
Ni1 O31 2.0699(13) . ?
Ni1 O32 2.0748(13) 3_566 ?
Ni1 N12 2.0793(15) . ?
Ni1 N22 2.0996(17) . ?
Ni1 N1 2.1419(15) . ?
N1T C2U 1.15(2) . ?
N1T C2T 1.155(7) . ?
C2T S3T 1.631(7) . ?
C2U S3U 1.65(2) . ?
N1 C10 1.482(2) . ?
N1 C20 1.487(2) . ?
N1 C2 1.489(2) . ?
C2 P3 1.8383(19) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
P3 O32 1.5065(13) . ?
P3 O31 1.5142(13) . ?
P3 C4 1.799(2) . ?
O32 Ni1 2.0748(13) 3_566 ?
C4 H41 0.9800 . ?
C4 H42 0.9800 . ?
C4 H43 0.9800 . ?
C10 C11 1.509(3) . ?
C10 H101 0.9900 . ?
C10 H102 0.9900 . ?
C11 N12 1.347(2) . ?
C11 C16 1.388(3) . ?
N12 C13 1.344(2) . ?
C13 C14 1.375(3) . ?
C13 H131 0.9500 . ?
C14 C15 1.386(3) . ?
C14 H141 0.9500 . ?
C15 C16 1.382(3) . ?
C15 H151 0.9500 . ?
C16 H161 0.9500 . ?
C20 C21 1.496(3) . ?
C20 H201 0.9900 . ?
C20 H202 0.9900 . ?
C21 N22 1.339(3) . ?
C21 C26 1.391(3) . ?
N22 C23 1.343(3) . ?
C23 C24 1.374(3) . ?
C23 H231 0.9500 . ?
C24 C25 1.377(4) . ?
C24 H241 0.9500 . ?
C25 C26 1.375(4) . ?
C25 H251 0.9500 . ?
C26 H261 0.9500 . ?

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
N1T Ni1 O31 99.40(6) . . ?
N1T Ni1 O32 91.66(6) . 3_566 ?
O31 Ni1 O32 91.16(5) . 3_566 ?
N1T Ni1 N12 95.31(6) . . ?
O31 Ni1 N12 165.14(6) . . ?
O32 Ni1 N12 86.32(5) 3_566 . ?
N1T Ni1 N22 91.94(7) . . ?
O31 Ni1 N22 86.09(6) . . ?
O32 Ni1 N22 175.79(6) 3_566 . ?
N12 Ni1 N22 95.53(6) . . ?
N1T Ni1 N1 170.10(6) . . ?
O31 Ni1 N1 87.17(5) . . ?
O32 Ni1 N1 95.63(6) 3_566 . ?
N12 Ni1 N1 78.52(6) . . ?
N22 Ni1 N1 81.07(6) . . ?
C2U N1T Ni1 161.2(12) . . ?
C2T N1T Ni1 160.2(3) . . ?
N1T C2T S3T 178.0(6) . . ?
N1T C2U S3U 175.6(17) . . ?
C10 N1 C20 110.12(15) . . ?
C10 N1 C2 112.46(14) . . ?
C20 N1 C2 112.34(15) . . ?
C10 N1 Ni1 104.09(11) . . ?
C20 N1 Ni1 107.35(11) . . ?
C2 N1 Ni1 110.04(11) . . ?
N1 C2 P3 113.08(12) . . ?
N1 C2 H21 109.0 . . ?
P3 C2 H21 109.0 . . ?
N1 C2 H22 109.0 . . ?
P3 C2 H22 109.0 . . ?
H21 C2 H22 107.8 . . ?
O32 P3 O31 117.64(8) . . ?
O32 P3 C4 106.97(9) . . ?
O31 P3 C4 109.19(9) . . ?
O32 P3 C2 107.68(8) . . ?
O31 P3 C2 106.57(8) . . ?
C4 P3 C2 108.51(10) . . ?
P3 O31 Ni1 117.42(7) . . ?
P3 O32 Ni1 133.90(7) . 3_566 ?
P3 C4 H41 109.5 . . ?
P3 C4 H42 109.5 . . ?
H41 C4 H42 109.5 . . ?
P3 C4 H43 109.5 . . ?
H41 C4 H43 109.5 . . ?
H42 C4 H43 109.5 . . ?
N1 C10 C11 109.05(15) . . ?
N1 C10 H101 109.9 . . ?
C11 C10 H101 109.9 . . ?
N1 C10 H102 109.9 . . ?
C11 C10 H102 109.9 . . ?
H101 C10 H102 108.3 . . ?
N12 C11 C16 121.82(17) . . ?
N12 C11 C10 115.91(16) . . ?
C16 C11 C10 122.25(17) . . ?
C13 N12 C11 118.78(16) . . ?
C13 N12 Ni1 127.68(12) . . ?
C11 N12 Ni1 113.41(12) . . ?
N12 C13 C14 122.57(18) . . ?
N12 C13 H131 118.7 . . ?
C14 C13 H131 118.7 . . ?
C13 C14 C15 118.53(18) . . ?
C13 C14 H141 120.7 . . ?
C15 C14 H141 120.7 . . ?
C16 C15 C14 119.60(18) . . ?
C16 C15 H151 120.2 . . ?
C14 C15 H151 120.2 . . ?
C15 C16 C11 118.69(18) . . ?
C15 C16 H161 120.7 . . ?
C11 C16 H161 120.7 . . ?
N1 C20 C21 113.23(16) . . ?
N1 C20 H201 108.9 . . ?
C21 C20 H201 108.9 . . ?
N1 C20 H202 108.9 . . ?
C21 C20 H202 108.9 . . ?
H201 C20 H202 107.7 . . ?
N22 C21 C26 121.7(2) . . ?
N22 C21 C20 116.15(18) . . ?
C26 C21 C20 122.1(2) . . ?
C21 N22 C23 118.63(19) . . ?
C21 N22 Ni1 114.51(13) . . ?
C23 N22 Ni1 125.68(16) . . ?
N22 C23 C24 122.3(2) . . ?
N22 C23 H231 118.8 . . ?
C24 C23 H231 118.8 . . ?
C23 C24 C25 119.2(3) . . ?
C23 C24 H241 120.4 . . ?
C25 C24 H241 120.4 . . ?
C26 C25 C24 119.0(2) . . ?
C26 C25 H251 120.5 . . ?
C24 C25 H251 120.5 . . ?
C25 C26 C21 119.1(2) . . ?
C25 C26 H261 120.4 . . ?
C21 C26 H261 120.4 . . ?

_refine_diff_density_max         0.622
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_vh044
_database_code_depnum_ccdc_archive 'CCDC 1815212'
_audit_update_record             
;
2018-01-07 deposited with the CCDC.
2018-03-26 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         'C13 H15 Cl Cu N3 O3 P'
_chemical_formula_sum            'C13 H15 Cl Cu N3 O3 P'
_chemical_formula_weight         391.24

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'
Cl Cl 0.1484 0.1585 '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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.2402(3)
_cell_length_b                   13.3847(4)
_cell_length_c                   12.0873(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.5790(10)
_cell_angle_gamma                90
_cell_volume                     1446.79(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9921
_cell_measurement_theta_min      2.3122
_cell_measurement_theta_max      27.5092

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.796
_exptl_crystal_F_000             796
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.083
_exptl_absorpt_coefficient_mu    1.820
_shelx_estimated_absorpt_T_min   0.662
_shelx_estimated_absorpt_T_max   0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1
;
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            3317
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.312
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3317
_reflns_number_gt                3104
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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 Instrument Service v2016.1.0.1'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+1.6173P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3317
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0809
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_restrained_S_all      1.114
_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
Cu1 Cu 0.69328(3) 0.61893(2) 0.63840(3) 0.00834(9) Uani 1 1 d . . . . .
Cl1 Cl 0.79107(7) 0.46980(4) 0.60811(6) 0.01512(14) Uani 1 1 d . . . . .
N1 N 0.5674(2) 0.74869(15) 0.60599(17) 0.0084(4) Uani 1 1 d . . . . .
C2 C 0.4816(3) 0.74841(17) 0.4836(2) 0.0081(4) Uani 1 1 d . . . . .
H21 H 0.4004 0.6985 0.4753 0.010 Uiso 1 1 calc R U . . .
H22 H 0.5495 0.7242 0.4378 0.010 Uiso 1 1 calc R U . . .
P3 P 0.39692(7) 0.86563(4) 0.41851(5) 0.00814(13) Uani 1 1 d . . . . .
O31 O 0.2802(2) 0.83289(14) 0.31595(16) 0.0140(4) Uani 1 1 d . . . . .
O32 O 0.5278(2) 0.91909(14) 0.37988(16) 0.0133(4) Uani 1 1 d . . . . .
H32O H 0.559(5) 0.970(4) 0.423(4) 0.055(14) Uiso 1 1 d . . . . .
O33 O 0.3473(2) 0.92745(13) 0.50679(16) 0.0114(4) Uani 1 1 d . . . . .
C10 C 0.4657(3) 0.74652(19) 0.6831(2) 0.0111(5) Uani 1 1 d . . . . .
H101 H 0.3789 0.7908 0.6530 0.013 Uiso 1 1 calc R U . . .
H102 H 0.5189 0.7708 0.7600 0.013 Uiso 1 1 calc R U . . .
C11 C 0.4126(3) 0.64056(19) 0.6913(2) 0.0114(5) Uani 1 1 d . . . . .
N12 N 0.5056(3) 0.56829(16) 0.67282(18) 0.0104(4) Uani 1 1 d . . . . .
C13 C 0.4677(3) 0.4723(2) 0.6809(2) 0.0147(5) Uani 1 1 d . . . . .
H131 H 0.5338 0.4216 0.6685 0.018 Uiso 1 1 calc R U . . .
C14 C 0.3356(3) 0.4446(2) 0.7066(3) 0.0190(6) Uani 1 1 d . . . . .
H141 H 0.3112 0.3760 0.7111 0.023 Uiso 1 1 calc R U . . .
C15 C 0.2399(3) 0.5179(2) 0.7257(2) 0.0192(6) Uani 1 1 d . . . . .
H151 H 0.1482 0.5007 0.7429 0.023 Uiso 1 1 calc R U . . .
C16 C 0.2799(3) 0.6174(2) 0.7192(2) 0.0164(6) Uani 1 1 d . . . . .
H161 H 0.2169 0.6691 0.7339 0.020 Uiso 1 1 calc R U . . .
C20 C 0.6808(3) 0.82901(17) 0.6329(2) 0.0104(5) Uani 1 1 d . . . . .
H201 H 0.7190 0.8359 0.7167 0.013 Uiso 1 1 calc R U . . .
H202 H 0.6357 0.8935 0.6017 0.013 Uiso 1 1 calc R U . . .
C21 C 0.8068(3) 0.80208(18) 0.5799(2) 0.0105(5) Uani 1 1 d . . . . .
N22 N 0.8348(2) 0.70308(15) 0.57643(19) 0.0111(4) Uani 1 1 d . . . . .
C23 C 0.9472(3) 0.67230(19) 0.5333(2) 0.0135(5) Uani 1 1 d . . . . .
H231 H 0.9655 0.6027 0.5296 0.016 Uiso 1 1 calc R U . . .
C24 C 1.0379(3) 0.7390(2) 0.4939(2) 0.0154(5) Uani 1 1 d . . . . .
H241 H 1.1187 0.7155 0.4656 0.018 Uiso 1 1 calc R U . . .
C25 C 1.0086(3) 0.8408(2) 0.4967(3) 0.0177(5) Uani 1 1 d . . . . .
H251 H 1.0687 0.8879 0.4698 0.021 Uiso 1 1 calc R U . . .
C26 C 0.8901(3) 0.87247(19) 0.5395(3) 0.0162(5) Uani 1 1 d . . . . .
H261 H 0.8667 0.9415 0.5409 0.019 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
Cu1 N12 2.001(2) . ?
Cu1 N22 2.008(2) . ?
Cu1 N1 2.072(2) . ?
Cu1 O31 2.1906(19) 4_676 ?
Cu1 Cl1 2.2586(6) . ?
N1 C20 1.479(3) . ?
N1 C10 1.481(3) . ?
N1 C2 1.493(3) . ?
C2 P3 1.839(2) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
P3 O31 1.4895(19) . ?
P3 O33 1.5100(18) . ?
P3 O32 1.5736(19) . ?
O31 Cu1 2.1907(19) 4_575 ?
O32 H32O 0.86(5) . ?
C10 C11 1.512(4) . ?
C10 H101 0.9900 . ?
C10 H102 0.9900 . ?
C11 N12 1.349(3) . ?
C11 C16 1.387(4) . ?
N12 C13 1.342(3) . ?
C13 C14 1.384(4) . ?
C13 H131 0.9500 . ?
C14 C15 1.378(4) . ?
C14 H141 0.9500 . ?
C15 C16 1.389(4) . ?
C15 H151 0.9500 . ?
C16 H161 0.9500 . ?
C20 C21 1.507(3) . ?
C20 H201 0.9900 . ?
C20 H202 0.9900 . ?
C21 N22 1.353(3) . ?
C21 C26 1.381(4) . ?
N22 C23 1.339(3) . ?
C23 C24 1.388(4) . ?
C23 H231 0.9500 . ?
C24 C25 1.391(4) . ?
C24 H241 0.9500 . ?
C25 C26 1.390(4) . ?
C25 H251 0.9500 . ?
C26 H261 0.9500 . ?

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
N12 Cu1 N22 161.34(9) . . ?
N12 Cu1 N1 81.29(8) . . ?
N22 Cu1 N1 81.18(8) . . ?
N12 Cu1 O31 91.11(8) . 4_676 ?
N22 Cu1 O31 95.03(8) . 4_676 ?
N1 Cu1 O31 89.34(8) . 4_676 ?
N12 Cu1 Cl1 97.90(6) . . ?
N22 Cu1 Cl1 96.35(6) . . ?
N1 Cu1 Cl1 159.81(6) . . ?
O31 Cu1 Cl1 110.85(5) 4_676 . ?
C20 N1 C10 113.73(19) . . ?
C20 N1 C2 112.95(19) . . ?
C10 N1 C2 111.2(2) . . ?
C20 N1 Cu1 103.57(15) . . ?
C10 N1 Cu1 106.22(15) . . ?
C2 N1 Cu1 108.55(14) . . ?
N1 C2 P3 118.97(16) . . ?
N1 C2 H21 107.6 . . ?
P3 C2 H21 107.6 . . ?
N1 C2 H22 107.6 . . ?
P3 C2 H22 107.6 . . ?
H21 C2 H22 107.0 . . ?
O31 P3 O33 117.66(11) . . ?
O31 P3 O32 109.65(11) . . ?
O33 P3 O32 110.69(10) . . ?
O31 P3 C2 104.23(11) . . ?
O33 P3 C2 109.72(11) . . ?
O32 P3 C2 103.82(11) . . ?
P3 O31 Cu1 137.63(11) . 4_575 ?
P3 O32 H32O 110(3) . . ?
N1 C10 C11 109.1(2) . . ?
N1 C10 H101 109.9 . . ?
C11 C10 H101 109.9 . . ?
N1 C10 H102 109.9 . . ?
C11 C10 H102 109.9 . . ?
H101 C10 H102 108.3 . . ?
N12 C11 C16 121.3(2) . . ?
N12 C11 C10 115.6(2) . . ?
C16 C11 C10 123.2(2) . . ?
C13 N12 C11 119.1(2) . . ?
C13 N12 Cu1 126.53(19) . . ?
C11 N12 Cu1 114.38(17) . . ?
N12 C13 C14 122.3(3) . . ?
N12 C13 H131 118.9 . . ?
C14 C13 H131 118.9 . . ?
C15 C14 C13 119.1(3) . . ?
C15 C14 H141 120.4 . . ?
C13 C14 H141 120.4 . . ?
C14 C15 C16 118.8(3) . . ?
C14 C15 H151 120.6 . . ?
C16 C15 H151 120.6 . . ?
C11 C16 C15 119.5(3) . . ?
C11 C16 H161 120.2 . . ?
C15 C16 H161 120.2 . . ?
N1 C20 C21 108.25(19) . . ?
N1 C20 H201 110.0 . . ?
C21 C20 H201 110.0 . . ?
N1 C20 H202 110.0 . . ?
C21 C20 H202 110.0 . . ?
H201 C20 H202 108.4 . . ?
N22 C21 C26 122.0(2) . . ?
N22 C21 C20 114.9(2) . . ?
C26 C21 C20 123.1(2) . . ?
C23 N22 C21 119.1(2) . . ?
C23 N22 Cu1 127.91(18) . . ?
C21 N22 Cu1 112.97(16) . . ?
N22 C23 C24 122.0(2) . . ?
N22 C23 H231 119.0 . . ?
C24 C23 H231 119.0 . . ?
C23 C24 C25 118.9(2) . . ?
C23 C24 H241 120.5 . . ?
C25 C24 H241 120.5 . . ?
C26 C25 C24 118.9(2) . . ?
C26 C25 H251 120.5 . . ?
C24 C25 H251 120.5 . . ?
C21 C26 C25 119.0(2) . . ?
C21 C26 H261 120.5 . . ?
C25 C26 H261 120.5 . . ?

_refine_diff_density_max         0.401
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.095

####################################################################### 
# 
# 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_dap
_database_code_depnum_ccdc_archive 'CCDC 1815209'
_audit_update_record             
;
2018-01-07 deposited with the CCDC.
2018-03-26 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         'C26 H30 Li2 N6 O6 P2'
_chemical_formula_sum            'C26 H30 Li2 N6 O6 P2'
_chemical_formula_weight         598.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Li Li 0.0008 0.0003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.3018(3)
_cell_length_b                   9.3173(3)
_cell_length_c                   16.7701(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.0570(10)
_cell_angle_gamma                90
_cell_volume                     1447.77(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9876
_cell_measurement_theta_min      5.2959
_cell_measurement_theta_max      72.2350

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.064
_exptl_absorpt_coefficient_mu    1.795
_shelx_estimated_absorpt_T_min   0.663
_shelx_estimated_absorpt_T_max   0.894
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS micro-focus sealed tube'
_diffrn_radiation_monochromator  'Helios Cu multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            20579
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.296
_diffrn_reflns_theta_max         72.229
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2864
_reflns_number_gt                2662
_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       'Bruker Instrument Service v2016.1.0.1'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0251P)²+1.7344P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2864
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.1023
_refine_ls_wR_factor_gt          0.1009
_refine_ls_goodness_of_fit_ref   1.236
_refine_ls_restrained_S_all      1.236
_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
Li1 Li 0.5672(4) 0.5262(4) 0.5754(2) 0.0188(7) Uani 1 1 d . . . . .
N1 N 0.68460(17) 0.36518(17) 0.66363(9) 0.0169(3) Uani 1 1 d . . . . .
C2 C 0.7187(2) 0.2408(2) 0.61516(12) 0.0191(4) Uani 1 1 d . . . . .
H21 H 0.7317 0.1550 0.6499 0.023 Uiso 1 1 calc R U . . .
H22 H 0.8104 0.2583 0.5910 0.023 Uiso 1 1 calc R U . . .
P3 P 0.57545(5) 0.20729(5) 0.53632(3) 0.01592(14) Uani 1 1 d . . . . .
O31 O 0.53707(15) 0.35324(15) 0.50273(8) 0.0209(3) Uani 1 1 d . . . . .
O32 O 0.65181(17) 0.11446(16) 0.47461(9) 0.0231(3) Uani 1 1 d . . . . .
H32O H 0.607(4) 0.033(4) 0.461(2) 0.069(11) Uiso 1 1 d . . . . .
O33 O 0.45356(15) 0.12554(15) 0.56933(9) 0.0227(3) Uani 1 1 d . . . . .
C10 C 0.8140(2) 0.4412(2) 0.69692(12) 0.0220(4) Uani 1 1 d . . . . .
H101 H 0.8867 0.3707 0.7188 0.026 Uiso 1 1 calc R U . . .
H102 H 0.7891 0.5038 0.7414 0.026 Uiso 1 1 calc R U . . .
C11 C 0.8773(2) 0.5312(2) 0.63371(12) 0.0195(4) Uani 1 1 d . . . . .
N12 N 0.78060(18) 0.60074(19) 0.58352(10) 0.0203(4) Uani 1 1 d . . . . .
C13 C 0.8302(2) 0.6893(2) 0.52920(13) 0.0237(4) Uani 1 1 d . . . . .
H131 H 0.7623 0.7401 0.4942 0.028 Uiso 1 1 calc R U . . .
C14 C 0.9758(2) 0.7102(2) 0.52182(13) 0.0253(5) Uani 1 1 d . . . . .
H141 H 1.0068 0.7748 0.4830 0.030 Uiso 1 1 calc R U . . .
C15 C 1.0747(2) 0.6355(2) 0.57172(13) 0.0266(5) Uani 1 1 d . . . . .
H151 H 1.1752 0.6455 0.5669 0.032 Uiso 1 1 calc R U . . .
C16 C 1.0250(2) 0.5452(2) 0.62930(13) 0.0243(5) Uani 1 1 d . . . . .
H161 H 1.0911 0.4938 0.6651 0.029 Uiso 1 1 calc R U . . .
C20 C 0.5854(2) 0.3333(2) 0.72402(12) 0.0218(4) Uani 1 1 d . . . . .
H201 H 0.6412 0.3002 0.7736 0.026 Uiso 1 1 calc R U . . .
H202 H 0.5200 0.2545 0.7045 0.026 Uiso 1 1 calc R U . . .
C21 C 0.4964(2) 0.4631(2) 0.74281(12) 0.0194(4) Uani 1 1 d . . . . .
N22 N 0.47517(18) 0.56309(19) 0.68543(10) 0.0201(4) Uani 1 1 d . . . . .
C23 C 0.3918(2) 0.6762(2) 0.69966(13) 0.0228(4) Uani 1 1 d . . . . .
H231 H 0.3792 0.7492 0.6601 0.027 Uiso 1 1 calc R U . . .
C24 C 0.3232(2) 0.6917(3) 0.76929(13) 0.0266(5) Uani 1 1 d . . . . .
H241 H 0.2633 0.7723 0.7766 0.032 Uiso 1 1 calc R U . . .
C25 C 0.3438(2) 0.5875(3) 0.82786(13) 0.0295(5) Uani 1 1 d . . . . .
H251 H 0.2971 0.5945 0.8759 0.035 Uiso 1 1 calc R U . . .
C26 C 0.4338(3) 0.4725(2) 0.81519(13) 0.0272(5) Uani 1 1 d . . . . .
H261 H 0.4525 0.4012 0.8552 0.033 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
Li1 O31 1.922(4) 3_666 ?
Li1 O31 2.025(4) . ?
Li1 N12 2.096(4) . ?
Li1 N22 2.130(4) . ?
Li1 N1 2.313(4) . ?
N1 C20 1.459(2) . ?
N1 C10 1.464(3) . ?
N1 C2 1.467(2) . ?
C2 P3 1.820(2) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
P3 O31 1.5028(15) . ?
P3 O33 1.5109(14) . ?
P3 O32 1.5662(14) . ?
O31 Li1 1.922(4) 3_666 ?
O32 H32O 0.89(4) . ?
C10 C11 1.511(3) . ?
C10 H101 0.9900 . ?
C10 H102 0.9900 . ?
C11 N12 1.343(3) . ?
C11 C16 1.388(3) . ?
N12 C13 1.341(3) . ?
C13 C14 1.384(3) . ?
C13 H131 0.9500 . ?
C14 C15 1.377(3) . ?
C14 H141 0.9500 . ?
C15 C16 1.390(3) . ?
C15 H151 0.9500 . ?
C16 H161 0.9500 . ?
C20 C21 1.515(3) . ?
C20 H201 0.9900 . ?
C20 H202 0.9900 . ?
C21 N22 1.341(3) . ?
C21 C26 1.395(3) . ?
N22 C23 1.342(3) . ?
C23 C24 1.387(3) . ?
C23 H231 0.9500 . ?
C24 C25 1.382(3) . ?
C24 H241 0.9500 . ?
C25 C26 1.388(3) . ?
C25 H251 0.9500 . ?
C26 H261 0.9500 . ?

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
O31 Li1 O31 91.17(15) 3_666 . ?
O31 Li1 N12 105.61(17) 3_666 . ?
O31 Li1 N12 112.53(17) . . ?
O31 Li1 N22 106.19(17) 3_666 . ?
O31 Li1 N22 127.22(18) . . ?
N12 Li1 N22 109.91(16) . . ?
O31 Li1 N1 175.32(19) 3_666 . ?
O31 Li1 N1 84.33(13) . . ?
N12 Li1 N1 77.42(13) . . ?
N22 Li1 N1 75.71(12) . . ?
C20 N1 C10 112.50(16) . . ?
C20 N1 C2 113.86(16) . . ?
C10 N1 C2 112.50(16) . . ?
C20 N1 Li1 106.54(15) . . ?
C10 N1 Li1 104.85(14) . . ?
C2 N1 Li1 105.73(14) . . ?
N1 C2 P3 110.95(13) . . ?
N1 C2 H21 109.4 . . ?
P3 C2 H21 109.4 . . ?
N1 C2 H22 109.4 . . ?
P3 C2 H22 109.4 . . ?
H21 C2 H22 108.0 . . ?
O31 P3 O33 115.62(9) . . ?
O31 P3 O32 111.02(8) . . ?
O33 P3 O32 111.25(8) . . ?
O31 P3 C2 104.59(9) . . ?
O33 P3 C2 110.21(9) . . ?
O32 P3 C2 103.23(9) . . ?
P3 O31 Li1 150.83(13) . 3_666 ?
P3 O31 Li1 118.62(13) . . ?
Li1 O31 Li1 88.82(15) 3_666 . ?
P3 O32 H32O 115(2) . . ?
N1 C10 C11 111.05(16) . . ?
N1 C10 H101 109.4 . . ?
C11 C10 H101 109.4 . . ?
N1 C10 H102 109.4 . . ?
C11 C10 H102 109.4 . . ?
H101 C10 H102 108.0 . . ?
N12 C11 C16 122.19(19) . . ?
N12 C11 C10 115.22(18) . . ?
C16 C11 C10 122.55(19) . . ?
C13 N12 C11 118.09(18) . . ?
C13 N12 Li1 122.70(17) . . ?
C11 N12 Li1 117.35(16) . . ?
N12 C13 C14 123.0(2) . . ?
N12 C13 H131 118.5 . . ?
C14 C13 H131 118.5 . . ?
C15 C14 C13 118.8(2) . . ?
C15 C14 H141 120.6 . . ?
C13 C14 H141 120.6 . . ?
C14 C15 C16 118.8(2) . . ?
C14 C15 H151 120.6 . . ?
C16 C15 H151 120.6 . . ?
C11 C16 C15 119.0(2) . . ?
C11 C16 H161 120.5 . . ?
C15 C16 H161 120.5 . . ?
N1 C20 C21 111.84(16) . . ?
N1 C20 H201 109.2 . . ?
C21 C20 H201 109.2 . . ?
N1 C20 H202 109.2 . . ?
C21 C20 H202 109.2 . . ?
H201 C20 H202 107.9 . . ?
N22 C21 C26 122.3(2) . . ?
N22 C21 C20 117.02(17) . . ?
C26 C21 C20 120.61(19) . . ?
C21 N22 C23 117.94(18) . . ?
C21 N22 Li1 117.68(16) . . ?
C23 N22 Li1 124.30(17) . . ?
N22 C23 C24 123.2(2) . . ?
N22 C23 H231 118.4 . . ?
C24 C23 H231 118.4 . . ?
C25 C24 C23 118.7(2) . . ?
C25 C24 H241 120.6 . . ?
C23 C24 H241 120.6 . . ?
C24 C25 C26 118.7(2) . . ?
C24 C25 H251 120.6 . . ?
C26 C25 H251 120.6 . . ?
C25 C26 C21 119.1(2) . . ?
C25 C26 H261 120.5 . . ?
C21 C26 H261 120.5 . . ?

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_dpap
_database_code_depnum_ccdc_archive 'CCDC 1815210'
_audit_update_record             
;
2018-01-07 deposited with the CCDC.
2018-03-26 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         'C13 H17 N3 O3 P, Cl, 2(H2 O)'
_chemical_formula_sum            'C13 H21 Cl N3 O5 P'
_chemical_formula_weight         365.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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'

_cell_length_a                   8.6070(2)
_cell_length_b                   25.0089(5)
_cell_length_c                   7.6190(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1640.00(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9886
_cell_measurement_theta_min      3.5346
_cell_measurement_theta_max      72.0130

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.059
_exptl_absorpt_coefficient_mu    3.254
_shelx_estimated_absorpt_T_min   0.624
_shelx_estimated_absorpt_T_max   0.831
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS micro-focus sealed tube'
_diffrn_radiation_monochromator  'Helios Cu multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            17980
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.534
_diffrn_reflns_theta_max         72.162
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3203
_reflns_number_gt                3093
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_max     0.975
_reflns_Friedel_fraction_full    0.982

_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 Instrument Service v2016.1.0.1'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0384P)²+0.4344P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1363 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3203
_refine_ls_number_parameters     236
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0659
_refine_ls_wR_factor_gt          0.0651
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.085
_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
N1 N 0.2698(2) 0.34181(8) 0.6578(3) 0.0133(4) Uani 1 1 d . . . . .
C2 C 0.2061(3) 0.33120(10) 0.4808(4) 0.0138(5) Uani 1 1 d . . . . .
H21 H 0.2224 0.3636 0.4084 0.017 Uiso 1 1 calc R U . . .
H22 H 0.0925 0.3261 0.4923 0.017 Uiso 1 1 calc R U . . .
P3 P 0.28427(6) 0.27416(2) 0.36053(9) 0.01226(15) Uani 1 1 d . . . . .
O31 O 0.1659(2) 0.26539(7) 0.2068(2) 0.0167(4) Uani 1 1 d . . . . .
H31O H 0.079(5) 0.2470(14) 0.236(5) 0.031(10) Uiso 1 1 d . . . . .
O32 O 0.4359(2) 0.29181(7) 0.2782(3) 0.0171(4) Uani 1 1 d . . . . .
O33 O 0.2940(2) 0.22654(7) 0.4812(3) 0.0181(4) Uani 1 1 d . . . . .
C10 C 0.1884(3) 0.31224(10) 0.7941(4) 0.0156(5) Uani 1 1 d . . . . .
H101 H 0.2532 0.3113 0.9014 0.019 Uiso 1 1 calc R U . . .
H102 H 0.1723 0.2749 0.7546 0.019 Uiso 1 1 calc R U . . .
C11 C 0.0331(3) 0.33700(10) 0.8372(3) 0.0147(5) Uani 1 1 d . . . . .
N12 N 0.0072(3) 0.38745(9) 0.7853(3) 0.0145(4) Uani 1 1 d . . . . .
H121 H 0.071(4) 0.4038(14) 0.716(5) 0.029(9) Uiso 1 1 d . . . . .
C13 C -0.1230(3) 0.41502(10) 0.8256(4) 0.0168(5) Uani 1 1 d . . . . .
H131 H -0.1353 0.4508 0.7864 0.020 Uiso 1 1 calc R U . . .
C14 C -0.2372(3) 0.39111(11) 0.9231(4) 0.0193(6) Uani 1 1 d . . . . .
H141 H -0.3288 0.4101 0.9538 0.023 Uiso 1 1 calc R U . . .
C15 C -0.2162(3) 0.33834(12) 0.9764(4) 0.0200(6) Uani 1 1 d . . . . .
H151 H -0.2946 0.3209 1.0429 0.024 Uiso 1 1 calc R U . . .
C16 C -0.0809(3) 0.31126(11) 0.9326(4) 0.0182(6) Uani 1 1 d . . . . .
H161 H -0.0668 0.2752 0.9681 0.022 Uiso 1 1 calc R U . . .
C20 C 0.4390(3) 0.33590(9) 0.6722(4) 0.0148(5) Uani 1 1 d . . . . .
H201 H 0.4699 0.3005 0.6258 0.018 Uiso 1 1 calc R U . . .
H202 H 0.4693 0.3374 0.7975 0.018 Uiso 1 1 calc R U . . .
C21 C 0.5243(3) 0.37902(10) 0.5725(4) 0.0145(5) Uani 1 1 d . . . . .
N22 N 0.6560(2) 0.36563(8) 0.4891(3) 0.0148(4) Uani 1 1 d . . . . .
H221 H 0.696(5) 0.3266(18) 0.486(7) 0.054(13) Uiso 1 1 d . . . . .
C23 C 0.7452(3) 0.40183(11) 0.4058(4) 0.0189(6) Uani 1 1 d . . . . .
H231 H 0.8373 0.3906 0.3480 0.023 Uiso 1 1 calc R U . . .
C24 C 0.7040(3) 0.45488(11) 0.4038(4) 0.0238(7) Uani 1 1 d . . . . .
H241 H 0.7666 0.4806 0.3452 0.029 Uiso 1 1 calc R U . . .
C25 C 0.5693(3) 0.46995(11) 0.4892(5) 0.0269(7) Uani 1 1 d . . . . .
H251 H 0.5388 0.5065 0.4898 0.032 Uiso 1 1 calc R U . . .
C26 C 0.4783(3) 0.43207(10) 0.5740(4) 0.0208(6) Uani 1 1 d . . . . .
H261 H 0.3855 0.4424 0.6324 0.025 Uiso 1 1 calc R U . . .
Cl1 Cl 0.10724(7) 0.44359(2) 0.17801(10) 0.02205(15) Uani 1 1 d . . . . .
O1W O 0.1266(2) 0.46731(8) 0.5781(3) 0.0212(4) Uani 1 1 d . . . . .
H11W H 0.115(5) 0.4638(19) 0.465(8) 0.061(15) Uiso 1 1 d . . . . .
H12W H 0.058(5) 0.4921(18) 0.588(7) 0.049(12) Uiso 1 1 d . . . . .
O2W O 0.4289(3) 0.38799(10) 1.0824(3) 0.0294(5) Uani 1 1 d . . . . .
H21W H 0.433(5) 0.3606(17) 1.143(6) 0.042(12) Uiso 1 1 d . . . . .
H22W H 0.348(6) 0.4059(19) 1.113(6) 0.053(13) Uiso 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
N1 C10 1.455(3) . ?
N1 C20 1.468(3) . ?
N1 C2 1.480(3) . ?
C2 P3 1.824(3) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
P3 O33 1.5069(19) . ?
P3 O32 1.5137(18) . ?
P3 O31 1.5677(19) . ?
O31 H31O 0.90(4) . ?
C10 C11 1.509(3) . ?
C10 H101 0.9900 . ?
C10 H102 0.9900 . ?
C11 N12 1.341(3) . ?
C11 C16 1.380(4) . ?
N12 C13 1.351(3) . ?
N12 H121 0.86(4) . ?
C13 C14 1.369(4) . ?
C13 H131 0.9500 . ?
C14 C15 1.393(4) . ?
C14 H141 0.9500 . ?
C15 C16 1.388(4) . ?
C15 H151 0.9500 . ?
C16 H161 0.9500 . ?
C20 C21 1.509(3) . ?
C20 H201 0.9900 . ?
C20 H202 0.9900 . ?
C21 N22 1.342(3) . ?
C21 C26 1.385(4) . ?
N22 C23 1.346(3) . ?
N22 H221 1.03(4) . ?
C23 C24 1.373(4) . ?
C23 H231 0.9500 . ?
C24 C25 1.381(4) . ?
C24 H241 0.9500 . ?
C25 C26 1.389(4) . ?
C25 H251 0.9500 . ?
C26 H261 0.9500 . ?
O1W H11W 0.87(6) . ?
O1W H12W 0.86(4) . ?
O2W H21W 0.83(5) . ?
O2W H22W 0.86(5) . ?

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
C10 N1 C20 111.9(2) . . ?
C10 N1 C2 112.38(19) . . ?
C20 N1 C2 114.7(2) . . ?
N1 C2 P3 117.46(16) . . ?
N1 C2 H21 107.9 . . ?
P3 C2 H21 107.9 . . ?
N1 C2 H22 107.9 . . ?
P3 C2 H22 107.9 . . ?
H21 C2 H22 107.2 . . ?
O33 P3 O32 115.81(10) . . ?
O33 P3 O31 112.42(10) . . ?
O32 P3 O31 106.93(11) . . ?
O33 P3 C2 109.40(12) . . ?
O32 P3 C2 107.36(11) . . ?
O31 P3 C2 104.17(10) . . ?
P3 O31 H31O 115(2) . . ?
N1 C10 C11 111.9(2) . . ?
N1 C10 H101 109.2 . . ?
C11 C10 H101 109.2 . . ?
N1 C10 H102 109.2 . . ?
C11 C10 H102 109.2 . . ?
H101 C10 H102 107.9 . . ?
N12 C11 C16 118.4(2) . . ?
N12 C11 C10 118.0(2) . . ?
C16 C11 C10 123.6(2) . . ?
C11 N12 C13 123.5(2) . . ?
C11 N12 H121 121(2) . . ?
C13 N12 H121 115(2) . . ?
N12 C13 C14 119.7(2) . . ?
N12 C13 H131 120.2 . . ?
C14 C13 H131 120.2 . . ?
C13 C14 C15 118.6(2) . . ?
C13 C14 H141 120.7 . . ?
C15 C14 H141 120.7 . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H151 120.0 . . ?
C14 C15 H151 120.0 . . ?
C11 C16 C15 119.7(2) . . ?
C11 C16 H161 120.1 . . ?
C15 C16 H161 120.1 . . ?
N1 C20 C21 111.9(2) . . ?
N1 C20 H201 109.2 . . ?
C21 C20 H201 109.2 . . ?
N1 C20 H202 109.2 . . ?
C21 C20 H202 109.2 . . ?
H201 C20 H202 107.9 . . ?
N22 C21 C26 119.0(2) . . ?
N22 C21 C20 118.1(2) . . ?
C26 C21 C20 122.8(2) . . ?
C21 N22 C23 122.5(2) . . ?
C21 N22 H221 122(3) . . ?
C23 N22 H221 116(3) . . ?
N22 C23 C24 120.5(3) . . ?
N22 C23 H231 119.7 . . ?
C24 C23 H231 119.7 . . ?
C23 C24 C25 118.3(3) . . ?
C23 C24 H241 120.8 . . ?
C25 C24 H241 120.8 . . ?
C24 C25 C26 120.4(3) . . ?
C24 C25 H251 119.8 . . ?
C26 C25 H251 119.8 . . ?
C21 C26 C25 119.2(3) . . ?
C21 C26 H261 120.4 . . ?
C25 C26 H261 120.4 . . ?
H11W O1W H12W 95(4) . . ?
H21W O2W H22W 108(4) . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_cudpbpin
_database_code_depnum_ccdc_archive 'CCDC 1815208'
_audit_update_record             
;
2018-01-07 deposited with the CCDC.
2018-03-26 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         'C14 H17 Cl Cu N3 O4 P2, H1.6 Na O0.8'
_chemical_formula_sum            'C14 H18.60 Cl Cu N3 Na O4.80 P2'
_chemical_formula_weight         489.64

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'
Cl Cl 0.1484 0.1585 '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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4334(3)
_cell_length_b                   8.5412(4)
_cell_length_c                   14.2914(6)
_cell_angle_alpha                86.225(2)
_cell_angle_beta                 77.544(2)
_cell_angle_gamma                73.399(2)
_cell_volume                     963.29(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9943
_cell_measurement_theta_min      2.8794
_cell_measurement_theta_max      27.4725

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_F_000             498
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.055
_exptl_absorpt_coefficient_mu    1.491
_shelx_estimated_absorpt_T_min   0.827
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            18699
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.488
_diffrn_reflns_theta_max         27.510
_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 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4414
_reflns_number_gt                4011
_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       'Bruker Instrument Service v2016.1.0.1'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0641P)²+3.1500P] 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         4414
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1274
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.51810(5) 0.43076(4) 0.13319(3) 0.01676(13) Uani 1 1 d . . . . .
Cl1 Cl 0.69201(10) 0.30973(10) -0.00225(6) 0.02377(18) Uani 1 1 d . . . . .
N1 N 0.3516(3) 0.5583(3) 0.25036(19) 0.0200(5) Uani 1 1 d . . . . .
C2 C 0.4135(5) 0.4976(4) 0.3398(2) 0.0254(7) Uani 1 1 d . . . . .
H21 H 0.3167 0.5210 0.3950 0.030 Uiso 1 1 calc R U . . .
H22 H 0.4935 0.5572 0.3496 0.030 Uiso 1 1 calc R U . . .
P3 P 0.51826(12) 0.27992(11) 0.33615(6) 0.0257(2) Uani 1 1 d . . . . .
O31 O 0.6421(3) 0.2437(3) 0.24291(17) 0.0269(5) Uani 1 1 d . . . . .
O32 O 0.3814(4) 0.1889(4) 0.3518(2) 0.0413(7) Uani 1 1 d . . . . .
C4 C 0.6155(5) 0.2495(5) 0.4391(3) 0.0356(9) Uani 1 1 d . . . . .
H41 H 0.5189 0.2623 0.4936 0.043 Uiso 1 1 d R U . A .
H42 H 0.6769 0.3362 0.4293 0.043 Uiso 1 1 d R U . . .
P5A P 0.7423(11) 0.0465(12) 0.4477(6) 0.0438(11) Uani 0.558(6) 1 d . . P A 1
H5PA H 0.6598 -0.0635 0.4027 0.053 Uiso 0.558(6) 1 d R U P A 1
O51A O 0.7419(10) 0.0001(10) 0.5528(5) 0.067(2) Uani 0.558(6) 1 d . . P A 1
O52A O 0.9176(9) 0.0319(12) 0.3866(6) 0.080(3) Uani 0.558(6) 1 d . . P A 1
P5B P 0.7729(14) 0.0650(15) 0.4617(8) 0.0438(11) Uani 0.442(6) 1 d . . P A 2
H5PB H 0.8670 0.0439 0.4039 0.053 Uiso 0.442(6) 1 calc R U P A 2
O51B O 0.6965(10) -0.0771(8) 0.4726(6) 0.046(2) Uani 0.442(6) 1 d . . P A 2
O52B O 0.8407(9) 0.1066(11) 0.5427(6) 0.054(2) Uani 0.442(6) 1 d . . P A 2
C10 C 0.1812(4) 0.5408(5) 0.2520(3) 0.0291(8) Uani 1 1 d . . . . .
H101 H 0.1165 0.6363 0.2197 0.035 Uiso 1 1 calc R U . . .
H102 H 0.1199 0.5388 0.3192 0.035 Uiso 1 1 calc R U . . .
C11 C 0.1917(4) 0.3864(4) 0.2024(2) 0.0220(6) Uani 1 1 d . . . . .
N12 N 0.3372(3) 0.3199(3) 0.14040(19) 0.0193(5) Uani 1 1 d . . . . .
C13 C 0.3506(4) 0.1846(4) 0.0921(2) 0.0225(6) Uani 1 1 d . . . . .
H131 H 0.4535 0.1366 0.0488 0.027 Uiso 1 1 calc R U . . .
C14 C 0.2193(5) 0.1134(4) 0.1036(3) 0.0287(7) Uani 1 1 d . . . . .
H141 H 0.2317 0.0182 0.0688 0.034 Uiso 1 1 calc R U . . .
C15 C 0.0694(5) 0.1837(5) 0.1668(3) 0.0318(8) Uani 1 1 d . . . . .
H151 H -0.0228 0.1377 0.1754 0.038 Uiso 1 1 calc R U . . .
C16 C 0.0552(5) 0.3210(5) 0.2171(3) 0.0297(8) Uani 1 1 d . . . . .
H161 H -0.0463 0.3700 0.2612 0.036 Uiso 1 1 calc R U . . .
C20 C 0.3557(4) 0.7312(4) 0.2347(2) 0.0231(7) Uani 1 1 d . . . . .
H201 H 0.3145 0.7908 0.2963 0.028 Uiso 1 1 calc R U . . .
H202 H 0.2812 0.7856 0.1903 0.028 Uiso 1 1 calc R U . . .
C21 C 0.5347(4) 0.7342(4) 0.1929(2) 0.0208(6) Uani 1 1 d . . . . .
N22 N 0.6323(3) 0.6027(3) 0.14108(19) 0.0185(5) Uani 1 1 d . . . . .
C23 C 0.7919(4) 0.6000(4) 0.0996(2) 0.0221(6) Uani 1 1 d . . . . .
H231 H 0.8620 0.5065 0.0637 0.027 Uiso 1 1 calc R U . . .
C24 C 0.8578(5) 0.7286(5) 0.1071(3) 0.0290(7) Uani 1 1 d . . . . .
H241 H 0.9710 0.7237 0.0766 0.035 Uiso 1 1 calc R U . . .
C25 C 0.7564(5) 0.8641(5) 0.1596(3) 0.0320(8) Uani 1 1 d . . . . .
H251 H 0.7986 0.9541 0.1655 0.038 Uiso 1 1 calc R U . . .
C26 C 0.5925(5) 0.8670(4) 0.2037(3) 0.0282(7) Uani 1 1 d . . . . .
H261 H 0.5209 0.9585 0.2408 0.034 Uiso 1 1 calc R U . . .
Na1W Na 0.7703(3) -0.4036(3) 0.39973(16) 0.0563(6) Uani 1 1 d . . . . .
O1WA O 0.9731(12) -0.6166(11) 0.4799(7) 0.091(3) Uiso 0.6 1 d . . P A .
O1WB O 1.0000 -0.5000 0.5000 0.075(4) Uiso 0.4 2 d S . P A .


_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 N22 1.994(3) . ?
Cu1 N12 1.995(3) . ?
Cu1 N1 2.077(3) . ?
Cu1 Cl1 2.2669(8) . ?
Cu1 O31 2.351(3) . ?
N1 C10 1.482(4) . ?
N1 C20 1.489(4) . ?
N1 C2 1.490(4) . ?
C2 P3 1.815(4) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
P3 O31 1.494(3) . ?
P3 O32 1.538(3) . ?
P3 C4 1.804(4) . ?
C4 P5A 1.771(10) . ?
C4 P5B 1.809(13) . ?
C4 H41 0.9839 . ?
C4 H42 1.0052 . ?
P5A O52A 1.522(12) . ?
P5A O51A 1.528(10) . ?
P5A H5PA 1.5573 . ?
P5B O52B 1.500(11) . ?
P5B O51B 1.514(12) . ?
P5B H5PB 1.0000 . ?
O51B Na1W 2.892(7) . ?
C10 C11 1.509(5) . ?
C10 H101 0.9900 . ?
C10 H102 0.9900 . ?
C11 N12 1.347(4) . ?
C11 C16 1.389(5) . ?
N12 C13 1.349(4) . ?
C13 C14 1.384(5) . ?
C13 H131 0.9500 . ?
C14 C15 1.385(6) . ?
C14 H141 0.9500 . ?
C15 C16 1.378(5) . ?
C15 H151 0.9500 . ?
C16 H161 0.9500 . ?
C20 C21 1.505(5) . ?
C20 H201 0.9900 . ?
C20 H202 0.9900 . ?
C21 N22 1.344(4) . ?
C21 C26 1.386(5) . ?
N22 C23 1.342(4) . ?
C23 C24 1.385(5) . ?
C23 H231 0.9500 . ?
C24 C25 1.381(6) . ?
C24 H241 0.9500 . ?
C25 C26 1.383(5) . ?
C25 H251 0.9500 . ?
C26 H261 0.9500 . ?
Na1W O1WA 2.518(10) . ?
Na1W O1WB 2.572(3) . ?
O1WA O1WB 1.149(9) . ?
O1WB O1WA 1.149(9) 2_746 ?
O1WB Na1W 2.572(3) 2_746 ?

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
N22 Cu1 N12 161.09(11) . . ?
N22 Cu1 N1 81.25(11) . . ?
N12 Cu1 N1 82.94(11) . . ?
N22 Cu1 Cl1 97.04(8) . . ?
N12 Cu1 Cl1 97.89(8) . . ?
N1 Cu1 Cl1 175.26(8) . . ?
N22 Cu1 O31 98.24(10) . . ?
N12 Cu1 O31 91.33(10) . . ?
N1 Cu1 O31 87.39(10) . . ?
Cl1 Cu1 O31 97.24(6) . . ?
C10 N1 C20 111.5(3) . . ?
C10 N1 C2 112.9(3) . . ?
C20 N1 C2 108.5(3) . . ?
C10 N1 Cu1 108.3(2) . . ?
C20 N1 Cu1 105.58(19) . . ?
C2 N1 Cu1 109.8(2) . . ?
N1 C2 P3 112.5(2) . . ?
N1 C2 H21 109.1 . . ?
P3 C2 H21 109.1 . . ?
N1 C2 H22 109.1 . . ?
P3 C2 H22 109.1 . . ?
H21 C2 H22 107.8 . . ?
O31 P3 O32 114.33(16) . . ?
O31 P3 C4 113.77(18) . . ?
O32 P3 C4 109.33(19) . . ?
O31 P3 C2 107.87(15) . . ?
O32 P3 C2 107.99(18) . . ?
C4 P3 C2 102.74(18) . . ?
P3 O31 Cu1 105.05(13) . . ?
P5A C4 P3 112.3(3) . . ?
P3 C4 P5B 124.0(4) . . ?
P5A C4 H41 105.3 . . ?
P3 C4 H41 103.4 . . ?
P5B C4 H41 106.5 . . ?
P5A C4 H42 115.8 . . ?
P3 C4 H42 101.9 . . ?
P5B C4 H42 104.3 . . ?
H41 C4 H42 117.6 . . ?
O52A P5A O51A 114.0(6) . . ?
O52A P5A C4 108.5(6) . . ?
O51A P5A C4 109.9(7) . . ?
O52A P5A H5PA 108.1 . . ?
O51A P5A H5PA 109.9 . . ?
C4 P5A H5PA 106.1 . . ?
O52B P5B O51B 119.3(9) . . ?
O52B P5B C4 105.1(8) . . ?
O51B P5B C4 109.1(6) . . ?
O52B P5B H5PB 107.6 . . ?
O51B P5B H5PB 107.6 . . ?
C4 P5B H5PB 107.6 . . ?
P5B O51B Na1W 139.7(7) . . ?
N1 C10 C11 111.4(3) . . ?
N1 C10 H101 109.3 . . ?
C11 C10 H101 109.3 . . ?
N1 C10 H102 109.3 . . ?
C11 C10 H102 109.3 . . ?
H101 C10 H102 108.0 . . ?
N12 C11 C16 121.9(3) . . ?
N12 C11 C10 116.5(3) . . ?
C16 C11 C10 121.5(3) . . ?
C11 N12 C13 118.7(3) . . ?
C11 N12 Cu1 115.1(2) . . ?
C13 N12 Cu1 126.2(2) . . ?
N12 C13 C14 122.1(3) . . ?
N12 C13 H131 118.9 . . ?
C14 C13 H131 118.9 . . ?
C13 C14 C15 118.8(3) . . ?
C13 C14 H141 120.6 . . ?
C15 C14 H141 120.6 . . ?
C16 C15 C14 119.5(3) . . ?
C16 C15 H151 120.3 . . ?
C14 C15 H151 120.3 . . ?
C15 C16 C11 119.0(3) . . ?
C15 C16 H161 120.5 . . ?
C11 C16 H161 120.5 . . ?
N1 C20 C21 108.9(3) . . ?
N1 C20 H201 109.9 . . ?
C21 C20 H201 109.9 . . ?
N1 C20 H202 109.9 . . ?
C21 C20 H202 109.9 . . ?
H201 C20 H202 108.3 . . ?
N22 C21 C26 122.2(3) . . ?
N22 C21 C20 115.6(3) . . ?
C26 C21 C20 122.1(3) . . ?
C23 N22 C21 118.5(3) . . ?
C23 N22 Cu1 126.8(2) . . ?
C21 N22 Cu1 114.6(2) . . ?
N22 C23 C24 122.3(3) . . ?
N22 C23 H231 118.8 . . ?
C24 C23 H231 118.8 . . ?
C25 C24 C23 118.9(3) . . ?
C25 C24 H241 120.5 . . ?
C23 C24 H241 120.5 . . ?
C24 C25 C26 119.2(3) . . ?
C24 C25 H251 120.4 . . ?
C26 C25 H251 120.4 . . ?
C25 C26 C21 118.8(3) . . ?
C25 C26 H261 120.6 . . ?
C21 C26 H261 120.6 . . ?
O1WA Na1W O1WB 26.1(2) . . ?
O1WA Na1W O51B 113.8(3) . . ?
O1WB Na1W O51B 89.00(17) . . ?
O1WB O1WA Na1W 79.6(5) . . ?
O1WA O1WB O1WA 180.0 . 2_746 ?
O1WA O1WB Na1W 74.4(5) . . ?
O1WA O1WB Na1W 105.6(5) 2_746 . ?
O1WA O1WB Na1W 105.6(5) . 2_746 ?
O1WA O1WB Na1W 74.4(5) 2_746 2_746 ?
Na1W O1WB Na1W 180.0 . 2_746 ?

_refine_diff_density_max         1.868
_refine_diff_density_min         -1.039
_refine_diff_density_rms         0.126

####################################################################### 
# 
# 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_cudpap-vb
_database_code_depnum_ccdc_archive 'CCDC 1815207'
_audit_update_record             
;
2018-01-07 deposited with the CCDC.
2018-03-26 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         
'C13 H16 Cl Cu N3 O3 P, C13 H15 Cl Cu N3 O3 P, Cl, H2 O'
_chemical_formula_sum            'C26 H33 Cl3 Cu2 N6 O7 P2'
_chemical_formula_weight         836.95

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'
Cl Cl 0.1484 0.1585 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.3721(2)
_cell_length_b                   22.6005(6)
_cell_length_c                   17.3031(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.159(2)
_cell_angle_gamma                90
_cell_volume                     3248.46(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      2.4519
_cell_measurement_theta_max      27.4191

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_F_000             1704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.136
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.106
_exptl_absorpt_coefficient_mu    1.709
_shelx_estimated_absorpt_T_min   0.801
_shelx_estimated_absorpt_T_max   0.840
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  0.84
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            45697
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.373
_diffrn_reflns_theta_max         27.539
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7476
_reflns_number_gt                5598
_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       'Bruker Instrument Service v2016.1.0.1'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0495P)²+13.3307P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7476
_refine_ls_number_parameters     431
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1379
_refine_ls_wR_factor_gt          0.1245
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
Cu1A Cu 0.72433(6) 0.70610(2) 0.18828(3) 0.02167(13) Uani 1 1 d . . . . .
Cl1A Cl 0.83678(13) 0.78305(5) 0.25924(7) 0.0306(2) Uani 1 1 d . . . . .
N1A N 0.6027(4) 0.64176(14) 0.1184(2) 0.0240(7) Uani 1 1 d . . . . .
C2A C 0.6441(5) 0.58224(18) 0.1528(3) 0.0302(10) Uani 1 1 d . . . . .
H2A H 0.6404 0.5529 0.1101 0.036 Uiso 1 1 calc R U . . .
H2B H 0.5612 0.5709 0.1862 0.036 Uiso 1 1 calc R U . . .
P3A P 0.84065(15) 0.57855(5) 0.21048(9) 0.0345(3) Uani 1 1 d . . . . .
O31A O 0.8713(4) 0.63563(13) 0.25165(19) 0.0300(7) Uani 1 1 d . . . . .
O32A O 0.8278(5) 0.52404(16) 0.2639(3) 0.0493(10) Uani 1 1 d D . . . .
H32A H 0.736(6) 0.528(4) 0.282(5) 0.10(3) Uiso 1 1 d D . . . .
O33A O 0.9724(5) 0.56480(18) 0.1599(3) 0.0527(11) Uani 1 1 d . . . . .
H33A H 0.970(12) 0.539(4) 0.123(6) 0.13(4) Uiso 1 1 d . . . . .
C10A C 0.6466(6) 0.6472(2) 0.0383(3) 0.0322(10) Uani 1 1 d . . . . .
H10A H 0.5605 0.6689 0.0055 0.039 Uiso 1 1 calc R U . . .
H10B H 0.6550 0.6072 0.0158 0.039 Uiso 1 1 calc R U . . .
C11A C 0.8042(6) 0.67938(18) 0.0372(3) 0.0280(9) Uani 1 1 d . . . . .
N12A N 0.8580(4) 0.71092(14) 0.1010(2) 0.0229(7) Uani 1 1 d . . . . .
C13A C 0.9961(5) 0.74187(18) 0.1007(3) 0.0255(9) Uani 1 1 d . . . . .
H13A H 1.0359 0.7636 0.1460 0.031 Uiso 1 1 calc R U . . .
C14A C 1.0815(6) 0.7435(2) 0.0381(3) 0.0359(11) Uani 1 1 d . . . . .
H14A H 1.1779 0.7659 0.0398 0.043 Uiso 1 1 calc R U . . .
C15A C 1.0231(7) 0.7116(3) -0.0276(3) 0.0479(14) Uani 1 1 d . . . . .
H15A H 1.0793 0.7119 -0.0720 0.057 Uiso 1 1 calc R U . . .
C16A C 0.8834(7) 0.6794(2) -0.0284(3) 0.0454(13) Uani 1 1 d . . . . .
H16A H 0.8419 0.6575 -0.0734 0.055 Uiso 1 1 calc R U . . .
C20A C 0.4291(5) 0.65399(19) 0.1209(3) 0.0282(9) Uani 1 1 d . . . . .
H20A H 0.3647 0.6184 0.1047 0.034 Uiso 1 1 calc R U . . .
H20B H 0.3932 0.6866 0.0846 0.034 Uiso 1 1 calc R U . . .
C21A C 0.4053(5) 0.67086(18) 0.2021(3) 0.0275(9) Uani 1 1 d . . . . .
N22A N 0.5309(4) 0.69784(14) 0.2441(2) 0.0242(7) Uani 1 1 d . . . . .
C23A C 0.5190(6) 0.7143(2) 0.3175(3) 0.0295(9) Uani 1 1 d . . . . .
H23A H 0.6088 0.7323 0.3474 0.035 Uiso 1 1 calc R U . . .
C24A C 0.3789(6) 0.7056(2) 0.3508(3) 0.0378(11) Uani 1 1 d . . . . .
H24A H 0.3726 0.7172 0.4031 0.045 Uiso 1 1 calc R U . . .
C25A C 0.2486(6) 0.6797(2) 0.3070(3) 0.0415(13) Uani 1 1 d . . . . .
H25A H 0.1504 0.6745 0.3284 0.050 Uiso 1 1 calc R U . . .
C26A C 0.2616(5) 0.6617(2) 0.2324(3) 0.0349(11) Uani 1 1 d . . . . .
H26A H 0.1733 0.6432 0.2018 0.042 Uiso 1 1 calc R U . . .
Cu1X Cu 0.37400(6) 0.37327(2) 0.37123(3) 0.02350(14) Uani 1 1 d . . . . .
Cl1X Cl 0.49756(13) 0.29695(4) 0.43680(7) 0.0307(2) Uani 1 1 d . . . . .
N1X N 0.2395(4) 0.43682(15) 0.3083(2) 0.0275(8) Uani 1 1 d . . . . .
C2X C 0.2691(5) 0.49609(17) 0.3451(3) 0.0308(10) Uani 1 1 d . . . . .
H2X H 0.2063 0.4995 0.3898 0.037 Uiso 1 1 calc R U . . .
H2Y H 0.2309 0.5271 0.3069 0.037 Uiso 1 1 calc R U . . .
P3X P 0.48050(15) 0.50825(5) 0.37882(7) 0.0283(3) Uani 1 1 d . . . . .
O31X O 0.5341(4) 0.45388(12) 0.42609(18) 0.0273(7) Uani 1 1 d . . . . .
O32X O 0.4798(5) 0.56468(13) 0.4304(2) 0.0344(8) Uani 1 1 d . . . . .
H32X H 0.470(8) 0.562(3) 0.472(4) 0.05(2) Uiso 1 1 d . . . . .
O33X O 0.5639(5) 0.52069(16) 0.3097(2) 0.0418(8) Uani 1 1 d . . . . .
C10X C 0.2804(6) 0.4354(2) 0.2265(3) 0.0368(11) Uani 1 1 d . . . . .
H10X H 0.1965 0.4130 0.1934 0.044 Uiso 1 1 calc R U . . .
H10Y H 0.2811 0.4763 0.2061 0.044 Uiso 1 1 calc R U . . .
C11X C 0.4402(6) 0.40763(19) 0.2218(3) 0.0326(10) Uani 1 1 d . . . . .
N12X N 0.4995(4) 0.37306(15) 0.2809(2) 0.0261(8) Uani 1 1 d . . . . .
C13X C 0.6403(5) 0.3442(2) 0.2777(3) 0.0312(10) Uani 1 1 d . . . . .
H13X H 0.6822 0.3199 0.3202 0.037 Uiso 1 1 calc R U . . .
C14X C 0.7247(6) 0.3491(2) 0.2143(3) 0.0399(12) Uani 1 1 d . . . . .
H14X H 0.8221 0.3279 0.2125 0.048 Uiso 1 1 calc R U . . .
C15X C 0.6635(7) 0.3859(2) 0.1531(3) 0.0449(13) Uani 1 1 d . . . . .
H15X H 0.7200 0.3906 0.1091 0.054 Uiso 1 1 calc R U . . .
C16X C 0.5204(7) 0.4156(2) 0.1566(3) 0.0430(13) Uani 1 1 d . . . . .
H16X H 0.4774 0.4409 0.1154 0.052 Uiso 1 1 calc R U . . .
C20X C 0.0709(5) 0.41863(19) 0.3144(3) 0.0344(11) Uani 1 1 d . . . . .
H20X H 0.0418 0.3839 0.2807 0.041 Uiso 1 1 calc R U . . .
H20Y H -0.0039 0.4513 0.2974 0.041 Uiso 1 1 calc R U . . .
C21X C 0.0587(5) 0.40327(18) 0.3979(3) 0.0316(11) Uani 1 1 d . . . . .
N22X N 0.1943(4) 0.37933(15) 0.4364(2) 0.0275(8) Uani 1 1 d . . . . .
C23X C 0.1980(6) 0.36567(19) 0.5117(3) 0.0316(10) Uani 1 1 d . . . . .
H23X H 0.2942 0.3496 0.5385 0.038 Uiso 1 1 calc R U . . .
C24X C 0.0673(6) 0.3740(2) 0.5520(4) 0.0436(13) Uani 1 1 d . . . . .
H24X H 0.0737 0.3647 0.6058 0.052 Uiso 1 1 calc R U . . .
C25X C -0.0739(6) 0.3965(2) 0.5116(4) 0.0469(15) Uani 1 1 d . . . . .
H25X H -0.1669 0.4015 0.5372 0.056 Uiso 1 1 calc R U . . .
C26X C -0.0777(6) 0.4115(2) 0.4337(4) 0.0404(13) Uani 1 1 d . . . . .
H26X H -0.1729 0.4272 0.4054 0.048 Uiso 1 1 calc R U . . .
Cl1 Cl 0.2906(3) 0.51569(8) 0.02322(11) 0.0739(5) Uani 1 1 d . . . . .
O1W O 0.9976(6) 0.4647(2) 0.0938(3) 0.0378(11) Uani 0.687(5) 1 d . . P A 1
H11W H 0.9154 0.4703 0.0605 0.045 Uiso 0.687(5) 1 d R U P A 1
H12W H 1.0967 0.4678 0.0735 0.045 Uiso 0.687(5) 1 d R U P A 1
O2W O 1.0123(13) 0.4730(5) -0.0306(6) 0.0378(11) Uani 0.313(5) 1 d . . P A 2
H21W H 1.0624 0.5115 -0.0261 0.045 Uiso 0.313(5) 1 d R U P A 2
H22W H 0.9121 0.4769 -0.0279 0.045 Uiso 0.313(5) 1 d R U P A 2


_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
Cu1A N12A 1.992(4) . ?
Cu1A N22A 1.995(4) . ?
Cu1A N1A 2.076(3) . ?
Cu1A O31A 2.217(3) . ?
Cu1A Cl1A 2.2650(11) . ?
N1A C10A 1.482(6) . ?
N1A C20A 1.485(6) . ?
N1A C2A 1.494(5) . ?
C2A P3A 1.817(5) . ?
C2A H2A 0.9900 . ?
C2A H2B 0.9900 . ?
P3A O31A 1.481(3) . ?
P3A O33A 1.523(4) . ?
P3A O32A 1.552(4) . ?
O32A H32A 0.87(2) . ?
O33A H33A 0.85(10) . ?
C10A C11A 1.508(6) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A N12A 1.343(6) . ?
C11A C16A 1.385(7) . ?
N12A C13A 1.352(5) . ?
C13A C14A 1.370(7) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.383(8) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.376(8) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
C20A C21A 1.494(7) . ?
C20A H20A 0.9900 . ?
C20A H20B 0.9900 . ?
C21A N22A 1.347(6) . ?
C21A C26A 1.386(6) . ?
N22A C23A 1.340(6) . ?
C23A C24A 1.384(7) . ?
C23A H23A 0.9500 . ?
C24A C25A 1.378(8) . ?
C24A H24A 0.9500 . ?
C25A C26A 1.371(8) . ?
C25A H25A 0.9500 . ?
C26A H26A 0.9500 . ?
Cu1X N12X 1.988(4) . ?
Cu1X N22X 1.995(4) . ?
Cu1X N1X 2.052(3) . ?
Cu1X Cl1X 2.2449(11) . ?
Cu1X O31X 2.387(3) . ?
N1X C20X 1.487(6) . ?
N1X C2X 1.491(5) . ?
N1X C10X 1.497(6) . ?
C2X P3X 1.814(5) . ?
C2X H2X 0.9900 . ?
C2X H2Y 0.9900 . ?
P3X O33X 1.485(4) . ?
P3X O31X 1.513(3) . ?
P3X O32X 1.557(4) . ?
O32X H32X 0.75(6) . ?
C10X C11X 1.489(7) . ?
C10X H10X 0.9900 . ?
C10X H10Y 0.9900 . ?
C11X N12X 1.333(6) . ?
C11X C16X 1.394(7) . ?
N12X C13X 1.355(6) . ?
C13X C14X 1.381(7) . ?
C13X H13X 0.9500 . ?
C14X C15X 1.394(8) . ?
C14X H14X 0.9500 . ?
C15X C16X 1.381(8) . ?
C15X H15X 0.9500 . ?
C16X H16X 0.9500 . ?
C20X C21X 1.501(7) . ?
C20X H20X 0.9900 . ?
C20X H20Y 0.9900 . ?
C21X N22X 1.355(6) . ?
C21X C26X 1.378(7) . ?
N22X C23X 1.334(6) . ?
C23X C24X 1.382(7) . ?
C23X H23X 0.9500 . ?
C24X C25X 1.392(8) . ?
C24X H24X 0.9500 . ?
C25X C26X 1.387(8) . ?
C25X H25X 0.9500 . ?
C26X H26X 0.9500 . ?
O1W H11W 0.8499 . ?
O1W H12W 0.9435 . ?
O2W O2W 1.64(2) 3_765 ?
O2W H21W 0.9636 . ?
O2W H22W 0.8499 . ?

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
N12A Cu1A N22A 159.86(15) . . ?
N12A Cu1A N1A 82.96(14) . . ?
N22A Cu1A N1A 81.23(15) . . ?
N12A Cu1A O31A 94.86(13) . . ?
N22A Cu1A O31A 97.33(13) . . ?
N1A Cu1A O31A 89.25(12) . . ?
N12A Cu1A Cl1A 97.72(10) . . ?
N22A Cu1A Cl1A 96.73(11) . . ?
N1A Cu1A Cl1A 173.97(10) . . ?
O31A Cu1A Cl1A 96.65(9) . . ?
C10A N1A C20A 111.7(4) . . ?
C10A N1A C2A 112.1(4) . . ?
C20A N1A C2A 109.6(3) . . ?
C10A N1A Cu1A 109.0(2) . . ?
C20A N1A Cu1A 105.3(3) . . ?
C2A N1A Cu1A 109.0(3) . . ?
N1A C2A P3A 114.2(3) . . ?
N1A C2A H2A 108.7 . . ?
P3A C2A H2A 108.7 . . ?
N1A C2A H2B 108.7 . . ?
P3A C2A H2B 108.7 . . ?
H2A C2A H2B 107.6 . . ?
O31A P3A O33A 111.1(2) . . ?
O31A P3A O32A 115.2(2) . . ?
O33A P3A O32A 106.8(2) . . ?
O31A P3A C2A 108.37(19) . . ?
O33A P3A C2A 111.4(3) . . ?
O32A P3A C2A 103.8(2) . . ?
P3A O31A Cu1A 109.61(17) . . ?
P3A O32A H32A 105(6) . . ?
P3A O33A H33A 128(7) . . ?
N1A C10A C11A 111.8(4) . . ?
N1A C10A H10A 109.3 . . ?
C11A C10A H10A 109.3 . . ?
N1A C10A H10B 109.3 . . ?
C11A C10A H10B 109.3 . . ?
H10A C10A H10B 107.9 . . ?
N12A C11A C16A 121.9(4) . . ?
N12A C11A C10A 116.7(4) . . ?
C16A C11A C10A 121.3(4) . . ?
C11A N12A C13A 118.1(4) . . ?
C11A N12A Cu1A 115.6(3) . . ?
C13A N12A Cu1A 126.4(3) . . ?
N12A C13A C14A 123.2(4) . . ?
N12A C13A H13A 118.4 . . ?
C14A C13A H13A 118.4 . . ?
C13A C14A C15A 118.0(5) . . ?
C13A C14A H14A 121.0 . . ?
C15A C14A H14A 121.0 . . ?
C16A C15A C14A 119.9(5) . . ?
C16A C15A H15A 120.1 . . ?
C14A C15A H15A 120.1 . . ?
C15A C16A C11A 119.0(5) . . ?
C15A C16A H16A 120.5 . . ?
C11A C16A H16A 120.5 . . ?
N1A C20A C21A 108.7(4) . . ?
N1A C20A H20A 109.9 . . ?
C21A C20A H20A 109.9 . . ?
N1A C20A H20B 109.9 . . ?
C21A C20A H20B 109.9 . . ?
H20A C20A H20B 108.3 . . ?
N22A C21A C26A 121.3(5) . . ?
N22A C21A C20A 115.8(4) . . ?
C26A C21A C20A 122.8(4) . . ?
C23A N22A C21A 119.5(4) . . ?
C23A N22A Cu1A 126.4(3) . . ?
C21A N22A Cu1A 114.1(3) . . ?
N22A C23A C24A 121.5(5) . . ?
N22A C23A H23A 119.2 . . ?
C24A C23A H23A 119.2 . . ?
C25A C24A C23A 119.0(5) . . ?
C25A C24A H24A 120.5 . . ?
C23A C24A H24A 120.5 . . ?
C26A C25A C24A 119.6(5) . . ?
C26A C25A H25A 120.2 . . ?
C24A C25A H25A 120.2 . . ?
C25A C26A C21A 119.0(5) . . ?
C25A C26A H26A 120.5 . . ?
C21A C26A H26A 120.5 . . ?
N12X Cu1X N22X 162.60(15) . . ?
N12X Cu1X N1X 83.86(15) . . ?
N22X Cu1X N1X 81.36(16) . . ?
N12X Cu1X Cl1X 98.04(11) . . ?
N22X Cu1X Cl1X 95.70(11) . . ?
N1X Cu1X Cl1X 173.59(11) . . ?
N12X Cu1X O31X 89.36(12) . . ?
N22X Cu1X O31X 98.55(12) . . ?
N1X Cu1X O31X 85.46(12) . . ?
Cl1X Cu1X O31X 100.65(8) . . ?
C20X N1X C2X 109.1(3) . . ?
C20X N1X C10X 113.1(4) . . ?
C2X N1X C10X 112.2(4) . . ?
C20X N1X Cu1X 103.4(3) . . ?
C2X N1X Cu1X 110.5(3) . . ?
C10X N1X Cu1X 108.2(3) . . ?
N1X C2X P3X 112.1(3) . . ?
N1X C2X H2X 109.2 . . ?
P3X C2X H2X 109.2 . . ?
N1X C2X H2Y 109.2 . . ?
P3X C2X H2Y 109.2 . . ?
H2X C2X H2Y 107.9 . . ?
O33X P3X O31X 116.8(2) . . ?
O33X P3X O32X 110.0(2) . . ?
O31X P3X O32X 112.16(18) . . ?
O33X P3X C2X 107.9(2) . . ?
O31X P3X C2X 105.23(19) . . ?
O32X P3X C2X 103.6(2) . . ?
P3X O31X Cu1X 106.90(15) . . ?
P3X O32X H32X 120(5) . . ?
C11X C10X N1X 112.0(4) . . ?
C11X C10X H10X 109.2 . . ?
N1X C10X H10X 109.2 . . ?
C11X C10X H10Y 109.2 . . ?
N1X C10X H10Y 109.2 . . ?
H10X C10X H10Y 107.9 . . ?
N12X C11X C16X 121.7(5) . . ?
N12X C11X C10X 117.1(4) . . ?
C16X C11X C10X 121.1(5) . . ?
C11X N12X C13X 119.5(4) . . ?
C11X N12X Cu1X 114.8(3) . . ?
C13X N12X Cu1X 125.5(3) . . ?
N12X C13X C14X 121.9(5) . . ?
N12X C13X H13X 119.1 . . ?
C14X C13X H13X 119.1 . . ?
C13X C14X C15X 118.4(5) . . ?
C13X C14X H14X 120.8 . . ?
C15X C14X H14X 120.8 . . ?
C16X C15X C14X 119.7(5) . . ?
C16X C15X H15X 120.2 . . ?
C14X C15X H15X 120.2 . . ?
C15X C16X C11X 118.8(5) . . ?
C15X C16X H16X 120.6 . . ?
C11X C16X H16X 120.6 . . ?
N1X C20X C21X 108.2(4) . . ?
N1X C20X H20X 110.1 . . ?
C21X C20X H20X 110.1 . . ?
N1X C20X H20Y 110.1 . . ?
C21X C20X H20Y 110.1 . . ?
H20X C20X H20Y 108.4 . . ?
N22X C21X C26X 121.5(5) . . ?
N22X C21X C20X 114.4(4) . . ?
C26X C21X C20X 124.1(4) . . ?
C23X N22X C21X 119.3(4) . . ?
C23X N22X Cu1X 127.4(3) . . ?
C21X N22X Cu1X 113.1(3) . . ?
N22X C23X C24X 122.4(5) . . ?
N22X C23X H23X 118.8 . . ?
C24X C23X H23X 118.8 . . ?
C23X C24X C25X 118.3(6) . . ?
C23X C24X H24X 120.9 . . ?
C25X C24X H24X 120.9 . . ?
C26X C25X C24X 119.5(5) . . ?
C26X C25X H25X 120.3 . . ?
C24X C25X H25X 120.3 . . ?
C21X C26X C25X 118.9(5) . . ?
C21X C26X H26X 120.5 . . ?
C25X C26X H26X 120.5 . . ?
H11W O1W H12W 114.3 . . ?
O2W O2W H21W 50.8 3_765 . ?
O2W O2W H22W 71.6 3_765 . ?
H21W O2W H22W 109.0 . . ?

_refine_diff_density_max         1.226
_refine_diff_density_min         -1.375
_refine_diff_density_rms         0.108

####################################################################### 
# 
# 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_cudpap
_database_code_depnum_ccdc_archive 'CCDC 1815206'
_audit_update_record             
;
2018-01-07 deposited with the CCDC.
2018-03-26 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         'C13 H15 Cl Cu N3 O3 P, 3(H2 O)'
_chemical_formula_sum            'C13 H21 Cl Cu N3 O6 P'
_chemical_formula_weight         445.29

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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0880(4)
_cell_length_b                   8.5326(5)
_cell_length_c                   14.6161(8)
_cell_angle_alpha                73.868(2)
_cell_angle_beta                 74.070(2)
_cell_angle_gamma                69.458(2)
_cell_volume                     889.62(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5679
_cell_measurement_theta_min      2.6026
_cell_measurement_theta_max      27.5366

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_F_000             458
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.262
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.065
_exptl_absorpt_coefficient_mu    1.503
_shelx_estimated_absorpt_T_min   0.694
_shelx_estimated_absorpt_T_max   0.909
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            15218
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.603
_diffrn_reflns_theta_max         27.593
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4103
_reflns_number_gt                3393
_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       'Bruker Instrument Service v2016.1.0.1'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0535P)²+0.1929P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4103
_refine_ls_number_parameters     251
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
Cu1 Cu 0.51642(4) 0.36543(3) 0.14468(2) 0.01714(10) Uani 1 1 d . . . . .
Cl1 Cl 0.69796(8) 0.29100(7) 0.00579(4) 0.02365(14) Uani 1 1 d . . . . .
N1 N 0.3449(3) 0.4527(2) 0.26752(13) 0.0173(4) Uani 1 1 d . . . . .
C2 C 0.4333(3) 0.3682(3) 0.35295(16) 0.0209(5) Uani 1 1 d . . . . .
H21 H 0.3403 0.3771 0.4132 0.025 Uiso 1 1 calc R U . . .
H22 H 0.5173 0.4291 0.3529 0.025 Uiso 1 1 calc R U . . .
P3 P 0.55636(8) 0.14468(7) 0.35319(4) 0.01822(14) Uani 1 1 d . . . . .
O31 O 0.6488(2) 0.1357(2) 0.25083(11) 0.0209(3) Uani 1 1 d . . . . .
O32 O 0.4130(2) 0.0440(2) 0.38397(14) 0.0254(4) Uani 1 1 d . . . . .
H32O H 0.389(4) 0.017(3) 0.438(2) 0.022(8) Uiso 1 1 d . . . . .
O33 O 0.6715(2) 0.0877(2) 0.42942(11) 0.0220(4) Uani 1 1 d . . . . .
C10 C 0.1705(3) 0.4204(3) 0.28267(18) 0.0251(5) Uani 1 1 d . . . . .
H101 H 0.0790 0.5293 0.2629 0.030 Uiso 1 1 calc R U . . .
H102 H 0.1309 0.3765 0.3526 0.030 Uiso 1 1 calc R U . . .
C11 C 0.1823(3) 0.2929(3) 0.22530(16) 0.0210(5) Uani 1 1 d . . . . .
N12 N 0.3228(3) 0.2668(2) 0.15096(13) 0.0176(4) Uani 1 1 d . . . . .
C13 C 0.3313(3) 0.1626(3) 0.09392(17) 0.0213(5) Uani 1 1 d . . . . .
H131 H 0.4301 0.1439 0.0410 0.026 Uiso 1 1 calc R U . . .
C14 C 0.2021(3) 0.0827(3) 0.10980(18) 0.0248(5) Uani 1 1 d . . . . .
H141 H 0.2111 0.0110 0.0681 0.030 Uiso 1 1 calc R U . . .
C15 C 0.0597(3) 0.1079(3) 0.18686(19) 0.0283(6) Uani 1 1 d . . . . .
H151 H -0.0306 0.0532 0.1995 0.034 Uiso 1 1 calc R U . . .
C16 C 0.0497(3) 0.2147(3) 0.24598(19) 0.0271(5) Uani 1 1 d . . . . .
H161 H -0.0471 0.2334 0.2999 0.032 Uiso 1 1 calc R U . . .
C20 C 0.3286(3) 0.6385(3) 0.24288(17) 0.0220(5) Uani 1 1 d . . . . .
H201 H 0.2777 0.6873 0.3023 0.026 Uiso 1 1 calc R U . . .
H202 H 0.2468 0.6995 0.1963 0.026 Uiso 1 1 calc R U . . .
C21 C 0.5124(3) 0.6605(3) 0.19867(16) 0.0195(5) Uani 1 1 d . . . . .
N22 N 0.6255(3) 0.5394(2) 0.14846(13) 0.0180(4) Uani 1 1 d . . . . .
C23 C 0.7920(3) 0.5489(3) 0.10671(16) 0.0208(5) Uani 1 1 d . . . . .
H231 H 0.8722 0.4635 0.0720 0.025 Uiso 1 1 calc R U . . .
C24 C 0.8511(4) 0.6789(3) 0.11232(18) 0.0254(5) Uani 1 1 d . . . . .
H241 H 0.9701 0.6826 0.0820 0.030 Uiso 1 1 calc R U . . .
C25 C 0.7347(4) 0.8032(3) 0.16257(18) 0.0283(6) Uani 1 1 d . . . . .
H251 H 0.7717 0.8949 0.1665 0.034 Uiso 1 1 calc R U . . .
C26 C 0.5638(3) 0.7924(3) 0.20712(17) 0.0238(5) Uani 1 1 d . . . . .
H261 H 0.4825 0.8753 0.2433 0.029 Uiso 1 1 calc R U . . .
O1W O 1.0595(4) 0.2256(4) 0.5850(3) 0.0727(9) Uani 1 1 d D . . . .
H11W H 1.119(5) 0.134(5) 0.584(3) 0.063(13) Uiso 1 1 d . . . . .
H12W H 0.971(4) 0.242(6) 0.561(3) 0.076 Uiso 1 1 d D U . . .
O2W O 0.7402(4) 0.2986(3) 0.52157(19) 0.0621(8) Uani 1 1 d D . . . .
H21W H 0.729(6) 0.230(4) 0.493(3) 0.080(14) Uiso 1 1 d D . . . .
H22W H 0.756(6) 0.397(6) 0.473(3) 0.096 Uiso 1 1 d . U . . .
O3W O 0.7145(4) 0.6069(3) 0.40228(17) 0.0561(7) Uani 1 1 d D . . . .
H31W H 0.615(4) 0.675(5) 0.391(3) 0.091(16) Uiso 1 1 d D . . . .
H32W H 0.789(6) 0.638(6) 0.418(4) 0.109 Uiso 1 1 d D 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
Cu1 N12 1.9929(19) . ?
Cu1 N22 1.9941(19) . ?
Cu1 N1 2.0863(18) . ?
Cu1 Cl1 2.2597(6) . ?
Cu1 O31 2.2685(15) . ?
N1 C10 1.477(3) . ?
N1 C2 1.489(3) . ?
N1 C20 1.491(3) . ?
C2 P3 1.815(2) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
P3 O31 1.4876(17) . ?
P3 O33 1.5149(16) . ?
P3 O32 1.5757(18) . ?
O32 H32O 0.75(3) . ?
C10 C11 1.512(3) . ?
C10 H101 0.9900 . ?
C10 H102 0.9900 . ?
C11 N12 1.342(3) . ?
C11 C16 1.379(3) . ?
N12 C13 1.352(3) . ?
C13 C14 1.375(3) . ?
C13 H131 0.9500 . ?
C14 C15 1.375(4) . ?
C14 H141 0.9500 . ?
C15 C16 1.389(4) . ?
C15 H151 0.9500 . ?
C16 H161 0.9500 . ?
C20 C21 1.504(3) . ?
C20 H201 0.9900 . ?
C20 H202 0.9900 . ?
C21 N22 1.354(3) . ?
C21 C26 1.374(3) . ?
N22 C23 1.338(3) . ?
C23 C24 1.382(3) . ?
C23 H231 0.9500 . ?
C24 C25 1.380(4) . ?
C24 H241 0.9500 . ?
C25 C26 1.380(4) . ?
C25 H251 0.9500 . ?
C26 H261 0.9500 . ?
O1W H11W 0.76(4) . ?
O1W H12W 0.836(19) . ?
O2W H21W 0.847(19) . ?
O2W H22W 0.96(5) . ?
O3W H31W 0.839(19) . ?
O3W H32W 0.841(19) . ?

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
N12 Cu1 N22 157.76(8) . . ?
N12 Cu1 N1 83.03(7) . . ?
N22 Cu1 N1 80.96(7) . . ?
N12 Cu1 Cl1 98.53(6) . . ?
N22 Cu1 Cl1 96.47(6) . . ?
N1 Cu1 Cl1 175.83(5) . . ?
N12 Cu1 O31 92.24(7) . . ?
N22 Cu1 O31 101.82(7) . . ?
N1 Cu1 O31 85.70(6) . . ?
Cl1 Cu1 O31 98.08(4) . . ?
C10 N1 C2 112.04(18) . . ?
C10 N1 C20 112.58(18) . . ?
C2 N1 C20 109.72(17) . . ?
C10 N1 Cu1 109.81(13) . . ?
C2 N1 Cu1 109.29(13) . . ?
C20 N1 Cu1 102.98(13) . . ?
N1 C2 P3 112.64(15) . . ?
N1 C2 H21 109.1 . . ?
P3 C2 H21 109.1 . . ?
N1 C2 H22 109.1 . . ?
P3 C2 H22 109.1 . . ?
H21 C2 H22 107.8 . . ?
O31 P3 O33 118.09(10) . . ?
O31 P3 O32 108.73(10) . . ?
O33 P3 O32 109.83(9) . . ?
O31 P3 C2 105.97(10) . . ?
O33 P3 C2 106.47(10) . . ?
O32 P3 C2 107.16(11) . . ?
P3 O31 Cu1 111.79(9) . . ?
P3 O32 H32O 112(2) . . ?
N1 C10 C11 111.98(19) . . ?
N1 C10 H101 109.2 . . ?
C11 C10 H101 109.2 . . ?
N1 C10 H102 109.2 . . ?
C11 C10 H102 109.2 . . ?
H101 C10 H102 107.9 . . ?
N12 C11 C16 122.1(2) . . ?
N12 C11 C10 116.7(2) . . ?
C16 C11 C10 121.1(2) . . ?
C11 N12 C13 118.4(2) . . ?
C11 N12 Cu1 115.72(15) . . ?
C13 N12 Cu1 125.51(16) . . ?
N12 C13 C14 122.4(2) . . ?
N12 C13 H131 118.8 . . ?
C14 C13 H131 118.8 . . ?
C13 C14 C15 119.1(2) . . ?
C13 C14 H141 120.5 . . ?
C15 C14 H141 120.5 . . ?
C14 C15 C16 119.0(2) . . ?
C14 C15 H151 120.5 . . ?
C16 C15 H151 120.5 . . ?
C11 C16 C15 119.0(2) . . ?
C11 C16 H161 120.5 . . ?
C15 C16 H161 120.5 . . ?
N1 C20 C21 108.88(18) . . ?
N1 C20 H201 109.9 . . ?
C21 C20 H201 109.9 . . ?
N1 C20 H202 109.9 . . ?
C21 C20 H202 109.9 . . ?
H201 C20 H202 108.3 . . ?
N22 C21 C26 121.8(2) . . ?
N22 C21 C20 114.6(2) . . ?
C26 C21 C20 123.6(2) . . ?
C23 N22 C21 118.6(2) . . ?
C23 N22 Cu1 127.48(16) . . ?
C21 N22 Cu1 113.89(15) . . ?
N22 C23 C24 122.2(2) . . ?
N22 C23 H231 118.9 . . ?
C24 C23 H231 118.9 . . ?
C25 C24 C23 119.0(2) . . ?
C25 C24 H241 120.5 . . ?
C23 C24 H241 120.5 . . ?
C24 C25 C26 119.0(2) . . ?
C24 C25 H251 120.5 . . ?
C26 C25 H251 120.5 . . ?
C21 C26 C25 119.3(2) . . ?
C21 C26 H261 120.3 . . ?
C25 C26 H261 120.3 . . ?
H11W O1W H12W 108(4) . . ?
H21W O2W H22W 107(4) . . ?
H31W O3W H32W 122(5) . . ?

_refine_diff_density_max         0.524
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_nidpabpin
_database_code_depnum_ccdc_archive 'CCDC 1815211'
_audit_update_record             
;
2018-01-07 deposited with the CCDC.
2018-03-26 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         'C15 H20 N4 Ni O5 P2 S, H2 O'
_chemical_formula_sum            'C15 H22 N4 Ni O6 P2 S'
_chemical_formula_weight         507.07

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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                   20.2640(9)
_cell_length_b                   13.5918(6)
_cell_length_c                   14.8142(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.348(2)
_cell_angle_gamma                90
_cell_volume                     4080.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9528
_cell_measurement_theta_min      2.2722
_cell_measurement_theta_max      27.4875

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_F_000             2096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.064
_exptl_absorpt_coefficient_mu    1.251
_shelx_estimated_absorpt_T_min   0.759
_shelx_estimated_absorpt_T_max   0.924
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            52717
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.265
_diffrn_reflns_theta_max         27.521
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4696
_reflns_number_gt                4296
_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       'Bruker Instrument Service v2016.1.0.1'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0282P)²+6.1114P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4696
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0229
_refine_ls_wR_factor_ref         0.0604
_refine_ls_wR_factor_gt          0.0584
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
Ni1 Ni 0.31918(2) 0.29425(2) 0.23760(2) 0.01288(6) Uani 1 1 d . . . . .
N1T N 0.35445(7) 0.17894(10) 0.16650(9) 0.0231(3) Uani 1 1 d . . . . .
C2T C 0.38867(8) 0.11368(11) 0.14787(10) 0.0194(3) Uani 1 1 d . . . . .
S3T S 0.43500(2) 0.01992(3) 0.12279(4) 0.03696(12) Uani 1 1 d . . . . .
O1C O 0.23940(6) 0.21260(9) 0.28196(9) 0.0221(2) Uani 1 1 d . . . . .
H11C H 0.1994(12) 0.2240(17) 0.2702(15) 0.035(6) Uiso 1 1 d . . . . .
H12C H 0.2422(12) 0.166(2) 0.3111(17) 0.044(7) Uiso 1 1 d . . . . .
N1 N 0.28981(6) 0.41769(9) 0.31426(8) 0.0129(2) Uani 1 1 d . . . . .
C2 C 0.22537(7) 0.45450(11) 0.28079(9) 0.0149(3) Uani 1 1 d . . . . .
H21 H 0.2186 0.5229 0.3017 0.018 Uiso 1 1 calc R U . . .
H22 H 0.1894 0.4134 0.3054 0.018 Uiso 1 1 calc R U . . .
P3 P 0.22292(2) 0.45069(3) 0.15806(2) 0.01386(8) Uani 1 1 d . . . . .
O31 O 0.25617(5) 0.35345(8) 0.13257(7) 0.0161(2) Uani 1 1 d . . . . .
O32 O 0.25049(6) 0.54370(8) 0.11942(7) 0.0198(2) Uani 1 1 d . . . . .
C4 C 0.13537(8) 0.44155(11) 0.13116(10) 0.0186(3) Uani 1 1 d . . . . .
H41 H 0.1117 0.4922 0.1665 0.022 Uiso 1 1 calc R U . . .
H42 H 0.1294 0.4580 0.0665 0.022 Uiso 1 1 calc R U . . .
P5 P 0.09646(2) 0.32475(3) 0.15155(3) 0.02019(9) Uani 1 1 d . . . . .
O51 O 0.10387(9) 0.25855(10) 0.06669(9) 0.0378(3) Uani 1 1 d . . . . .
H51O H 0.1422(15) 0.230(2) 0.061(2) 0.062(9) Uiso 1 1 d . . . . .
O52 O 0.11650(6) 0.27803(8) 0.23824(8) 0.0224(2) Uani 1 1 d . . . . .
H51P H 0.0312(8) 0.3430(12) 0.1529(10) 0.006(4) Uiso 1 1 d . . . . .
C10 C 0.28373(7) 0.38342(11) 0.40882(9) 0.0160(3) Uani 1 1 d . . . . .
H101 H 0.2410 0.3492 0.4168 0.019 Uiso 1 1 calc R U . . .
H102 H 0.2849 0.4405 0.4503 0.019 Uiso 1 1 calc R U . . .
C11 C 0.33964(7) 0.31436(11) 0.43099(10) 0.0152(3) Uani 1 1 d . . . . .
N12 N 0.36589(6) 0.26446(9) 0.36110(8) 0.0155(2) Uani 1 1 d . . . . .
C13 C 0.41523(8) 0.20113(11) 0.37831(11) 0.0180(3) Uani 1 1 d . . . . .
H131 H 0.4350 0.1675 0.3291 0.022 Uiso 1 1 calc R U . . .
C14 C 0.43852(8) 0.18281(12) 0.46457(11) 0.0222(3) Uani 1 1 d . . . . .
H141 H 0.4732 0.1369 0.4744 0.027 Uiso 1 1 calc R U . . .
C15 C 0.41037(8) 0.23255(13) 0.53654(11) 0.0234(3) Uani 1 1 d . . . . .
H151 H 0.4247 0.2201 0.5966 0.028 Uiso 1 1 calc R U . . .
C16 C 0.36090(8) 0.30073(11) 0.51928(10) 0.0192(3) Uani 1 1 d . . . . .
H161 H 0.3419 0.3374 0.5671 0.023 Uiso 1 1 calc R U . . .
C20 C 0.34251(7) 0.49370(10) 0.30716(10) 0.0156(3) Uani 1 1 d . . . . .
H201 H 0.3692 0.4930 0.3634 0.019 Uiso 1 1 calc R U . . .
H202 H 0.3216 0.5593 0.3021 0.019 Uiso 1 1 calc R U . . .
C21 C 0.38776(7) 0.47909(11) 0.22791(9) 0.0144(3) Uani 1 1 d . . . . .
N22 N 0.39182(6) 0.38756(9) 0.19455(8) 0.0145(2) Uani 1 1 d . . . . .
C23 C 0.43703(8) 0.36835(12) 0.13068(10) 0.0187(3) Uani 1 1 d . . . . .
H231 H 0.4395 0.3038 0.1064 0.022 Uiso 1 1 calc R U . . .
C24 C 0.47990(8) 0.43930(12) 0.09929(11) 0.0217(3) Uani 1 1 d . . . . .
H241 H 0.5128 0.4231 0.0564 0.026 Uiso 1 1 calc R U . . .
C25 C 0.47403(8) 0.53475(12) 0.13163(11) 0.0219(3) Uani 1 1 d . . . . .
H251 H 0.5020 0.5853 0.1097 0.026 Uiso 1 1 calc R U . . .
C26 C 0.42684(8) 0.55539(11) 0.19627(10) 0.0184(3) Uani 1 1 d . . . . .
H261 H 0.4214 0.6204 0.2185 0.022 Uiso 1 1 calc R U . . .
O1W O 0.21002(8) 0.15929(10) 0.04580(9) 0.0328(3) Uani 1 1 d . . . . .
H11W H 0.2417(16) 0.179(2) 0.072(2) 0.070(10) Uiso 1 1 d . . . . .
H12W H 0.2221(15) 0.151(2) -0.013(2) 0.075(9) Uiso 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
Ni1 N1T 2.0213(13) . ?
Ni1 N22 2.0477(12) . ?
Ni1 O1C 2.0712(12) . ?
Ni1 N12 2.0943(13) . ?
Ni1 N1 2.1134(12) . ?
Ni1 O31 2.1622(10) . ?
N1T C2T 1.160(2) . ?
C2T S3T 1.6272(16) . ?
O1C H11C 0.84(3) . ?
O1C H12C 0.77(3) . ?
N1 C2 1.4811(18) . ?
N1 C10 1.4821(17) . ?
N1 C20 1.4900(18) . ?
C2 P3 1.8193(14) . ?
C2 H21 0.9900 . ?
C2 H22 0.9900 . ?
P3 O32 1.4972(11) . ?
P3 O31 1.5318(11) . ?
P3 C4 1.8201(16) . ?
C4 P5 1.7990(16) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
P5 O52 1.4870(12) . ?
P5 O51 1.5540(14) . ?
P5 H51P 1.346(15) . ?
O51 H51O 0.87(3) . ?
C10 C11 1.506(2) . ?
C10 H101 0.9900 . ?
C10 H102 0.9900 . ?
C11 N12 1.3497(18) . ?
C11 C16 1.387(2) . ?
N12 C13 1.3426(19) . ?
C13 C14 1.382(2) . ?
C13 H131 0.9500 . ?
C14 C15 1.388(2) . ?
C14 H141 0.9500 . ?
C15 C16 1.388(2) . ?
C15 H151 0.9500 . ?
C16 H161 0.9500 . ?
C20 C21 1.5072(19) . ?
C20 H201 0.9900 . ?
C20 H202 0.9900 . ?
C21 N22 1.3414(18) . ?
C21 C26 1.388(2) . ?
N22 C23 1.3466(18) . ?
C23 C24 1.380(2) . ?
C23 H231 0.9500 . ?
C24 C25 1.388(2) . ?
C24 H241 0.9500 . ?
C25 C26 1.386(2) . ?
C25 H251 0.9500 . ?
C26 H261 0.9500 . ?
O1W H11W 0.79(3) . ?
O1W H12W 0.91(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1T Ni1 N22 93.48(5) . . ?
N1T Ni1 O1C 91.66(5) . . ?
N22 Ni1 O1C 174.04(5) . . ?
N1T Ni1 N12 98.39(5) . . ?
N22 Ni1 N12 94.01(5) . . ?
O1C Ni1 N12 88.21(5) . . ?
N1T Ni1 N1 175.65(5) . . ?
N22 Ni1 N1 83.17(5) . . ?
O1C Ni1 N1 91.83(5) . . ?
N12 Ni1 N1 79.13(5) . . ?
N1T Ni1 O31 97.04(5) . . ?
N22 Ni1 O31 88.16(4) . . ?
O1C Ni1 O31 88.23(5) . . ?
N12 Ni1 O31 164.25(4) . . ?
N1 Ni1 O31 85.66(4) . . ?
C2T N1T Ni1 158.51(14) . . ?
N1T C2T S3T 178.31(14) . . ?
Ni1 O1C H11C 126.0(15) . . ?
Ni1 O1C H12C 124.4(19) . . ?
H11C O1C H12C 110(2) . . ?
C2 N1 C10 110.14(11) . . ?
C2 N1 C20 111.90(11) . . ?
C10 N1 C20 110.38(11) . . ?
C2 N1 Ni1 109.81(8) . . ?
C10 N1 Ni1 106.48(8) . . ?
C20 N1 Ni1 107.95(8) . . ?
N1 C2 P3 110.09(9) . . ?
N1 C2 H21 109.6 . . ?
P3 C2 H21 109.6 . . ?
N1 C2 H22 109.6 . . ?
P3 C2 H22 109.6 . . ?
H21 C2 H22 108.2 . . ?
O32 P3 O31 117.93(6) . . ?
O32 P3 C2 110.49(7) . . ?
O31 P3 C2 105.16(6) . . ?
O32 P3 C4 109.84(7) . . ?
O31 P3 C4 108.47(7) . . ?
C2 P3 C4 103.97(7) . . ?
P3 O31 Ni1 113.73(6) . . ?
P5 C4 P3 116.81(8) . . ?
P5 C4 H41 108.1 . . ?
P3 C4 H41 108.1 . . ?
P5 C4 H42 108.1 . . ?
P3 C4 H42 108.1 . . ?
H41 C4 H42 107.3 . . ?
O52 P5 O51 115.10(8) . . ?
O52 P5 C4 113.84(7) . . ?
O51 P5 C4 109.30(8) . . ?
O52 P5 H51P 109.2(7) . . ?
O51 P5 H51P 102.6(7) . . ?
C4 P5 H51P 105.7(7) . . ?
P5 O51 H51O 115(2) . . ?
N1 C10 C11 109.59(11) . . ?
N1 C10 H101 109.8 . . ?
C11 C10 H101 109.8 . . ?
N1 C10 H102 109.8 . . ?
C11 C10 H102 109.8 . . ?
H101 C10 H102 108.2 . . ?
N12 C11 C16 122.31(14) . . ?
N12 C11 C10 116.45(12) . . ?
C16 C11 C10 121.19(13) . . ?
C13 N12 C11 118.24(13) . . ?
C13 N12 Ni1 128.46(10) . . ?
C11 N12 Ni1 113.25(10) . . ?
N12 C13 C14 122.73(14) . . ?
N12 C13 H131 118.6 . . ?
C14 C13 H131 118.6 . . ?
C13 C14 C15 118.87(14) . . ?
C13 C14 H141 120.6 . . ?
C15 C14 H141 120.6 . . ?
C16 C15 C14 118.92(15) . . ?
C16 C15 H151 120.5 . . ?
C14 C15 H151 120.5 . . ?
C11 C16 C15 118.87(14) . . ?
C11 C16 H161 120.6 . . ?
C15 C16 H161 120.6 . . ?
N1 C20 C21 113.78(11) . . ?
N1 C20 H201 108.8 . . ?
C21 C20 H201 108.8 . . ?
N1 C20 H202 108.8 . . ?
C21 C20 H202 108.8 . . ?
H201 C20 H202 107.7 . . ?
N22 C21 C26 122.15(13) . . ?
N22 C21 C20 116.62(12) . . ?
C26 C21 C20 121.04(13) . . ?
C21 N22 C23 118.83(13) . . ?
C21 N22 Ni1 114.45(9) . . ?
C23 N22 Ni1 126.31(10) . . ?
N22 C23 C24 122.24(14) . . ?
N22 C23 H231 118.9 . . ?
C24 C23 H231 118.9 . . ?
C23 C24 C25 118.76(14) . . ?
C23 C24 H241 120.6 . . ?
C25 C24 H241 120.6 . . ?
C26 C25 C24 119.24(14) . . ?
C26 C25 H251 120.4 . . ?
C24 C25 H251 120.4 . . ?
C25 C26 C21 118.65(14) . . ?
C25 C26 H261 120.7 . . ?
C21 C26 H261 120.7 . . ?
H11W O1W H12W 106(3) . . ?

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.060

