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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_l1022a
_audit_block_doi                 10.5517/ccdc.csd.cc24tn5t
_database_code_depnum_ccdc_archive 'CCDC 1990856'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv.12023352 2020
loop_
_audit_author_name
_audit_author_address
'Martin Lutz'
;Utrecht University
Netherlands
;
_audit_update_record             
;
2020-03-17 deposited with the CCDC.	2020-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H32 Cl2 Cu2 N2 O2 P2, C4 H8 O'
_chemical_formula_sum            'C24 H40 Cl2 Cu2 N2 O3 P2'
_chemical_formula_weight         664.50

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      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                   17.8896(5)
_cell_length_b                   11.8315(3)
_cell_length_c                   14.1427(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2993.45(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    24302
_cell_measurement_theta_min      2.02
_cell_measurement_theta_max      25.58



loop_
_diffrn_orient_matrix_type
_diffrn_orient_matrix_UB_11
_diffrn_orient_matrix_UB_12
_diffrn_orient_matrix_UB_13
_diffrn_orient_matrix_UB_21
_diffrn_orient_matrix_UB_22
_diffrn_orient_matrix_UB_23
_diffrn_orient_matrix_UB_31
_diffrn_orient_matrix_UB_32
_diffrn_orient_matrix_UB_33
'Nonius RMAT' 0.0456361 0.0397046 0.0237917 0.0134092 0.0215006 -0.0662606
-0.0293789 0.0714891 0.0067143

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    1.734
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5804
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38868
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.064
_diffrn_reflns_theta_max         25.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5568
_reflns_number_gt                4828
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.917
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       Apex3
_computing_cell_refinement       Peakref
_computing_data_reduction        'Eval15, Sadabs'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion 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)+(0.0569P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.48(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5568
_refine_ls_number_parameters     325
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0923
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_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 0.67482(4) 0.27635(6) 0.51328(5) 0.0272(2) Uani 1 1 d . . . . .
Cu2 Cu 0.66945(4) 0.29500(6) 0.32153(5) 0.0263(2) Uani 1 1 d . . . . .
Cl1 Cl 0.72879(7) 0.14927(12) 0.40562(11) 0.0294(3) Uani 1 1 d . . . . .
Cl2 Cl 0.70363(8) 0.43914(12) 0.42828(12) 0.0333(4) Uani 1 1 d . . . . .
P1 P 0.65372(8) 0.25046(14) 0.66199(12) 0.0240(3) Uani 1 1 d . . . . .
P2 P 0.63872(8) 0.31469(14) 0.17404(12) 0.0242(3) Uani 1 1 d . . . . .
O1 O 0.5598(2) 0.2322(3) 0.6633(3) 0.0271(9) Uani 1 1 d . . . . .
O2 O 0.5461(2) 0.2873(3) 0.1773(3) 0.0295(10) Uani 1 1 d . . . . .
N1 N 0.5545(3) 0.2486(4) 0.5010(4) 0.0215(10) Uani 1 1 d . . . . .
N2 N 0.5497(3) 0.2662(4) 0.3392(4) 0.0237(12) Uani 1 1 d . . . . .
C1 C 0.5217(3) 0.2263(5) 0.5817(5) 0.0241(14) Uani 1 1 d . . . . .
C2 C 0.4445(3) 0.1944(5) 0.5910(5) 0.0253(14) Uani 1 1 d . . . . .
H2 H 0.423459 0.177010 0.650896 0.030 Uiso 1 1 calc R U . . .
C3 C 0.4025(3) 0.1901(5) 0.5103(5) 0.0238(13) Uani 1 1 d . . . . .
H3 H 0.351098 0.169982 0.513403 0.029 Uiso 1 1 calc R U . . .
C4 C 0.4359(3) 0.2158(5) 0.4224(6) 0.0233(11) Uani 1 1 d . . . . .
C5 C 0.5129(3) 0.2438(4) 0.4212(5) 0.0205(11) Uani 1 1 d . . . . .
C6 C 0.3975(3) 0.2152(5) 0.3355(5) 0.0244(14) Uani 1 1 d . . . . .
H6 H 0.345615 0.198274 0.333631 0.029 Uiso 1 1 calc R U . . .
C7 C 0.4346(4) 0.2387(5) 0.2550(5) 0.0281(14) Uani 1 1 d . . . . .
H7 H 0.409470 0.237952 0.195852 0.034 Uiso 1 1 calc R U . . .
C8 C 0.5118(3) 0.2645(5) 0.2602(4) 0.0225(13) Uani 1 1 d . . . . .
C9 C 0.6804(3) 0.1204(6) 0.7250(4) 0.0300(15) Uani 1 1 d . . . . .
H9 H 0.735960 0.121859 0.733010 0.036 Uiso 1 1 calc R U . . .
C10 C 0.6617(4) 0.0196(6) 0.6624(5) 0.0389(15) Uani 1 1 d . . . . .
H10A H 0.686166 -0.048222 0.687393 0.058 Uiso 1 1 calc R U . . .
H10B H 0.679305 0.033975 0.597947 0.058 Uiso 1 1 calc R U . . .
H10C H 0.607407 0.008084 0.661695 0.058 Uiso 1 1 calc R U . . .
C11 C 0.6463(4) 0.1076(6) 0.8225(5) 0.0394(16) Uani 1 1 d . . . . .
H11A H 0.591921 0.100153 0.816759 0.059 Uiso 1 1 calc R U . . .
H11B H 0.658178 0.174314 0.860700 0.059 Uiso 1 1 calc R U . . .
H11C H 0.666706 0.039976 0.853105 0.059 Uiso 1 1 calc R U . . .
C12 C 0.6608(4) 0.3635(6) 0.7492(5) 0.0357(16) Uani 1 1 d . . . . .
H12 H 0.628869 0.344781 0.805028 0.043 Uiso 1 1 calc R U . . .
C13 C 0.7431(4) 0.3703(6) 0.7804(5) 0.0474(19) Uani 1 1 d . . . . .
H13A H 0.774901 0.382911 0.724999 0.071 Uiso 1 1 calc R U . . .
H13B H 0.757452 0.299306 0.811168 0.071 Uiso 1 1 calc R U . . .
H13C H 0.749352 0.432989 0.825024 0.071 Uiso 1 1 calc R U . . .
C14 C 0.6344(5) 0.4739(6) 0.7058(6) 0.052(2) Uani 1 1 d . . . . .
H14A H 0.642071 0.535611 0.751081 0.079 Uiso 1 1 calc R U . . .
H14B H 0.581110 0.468221 0.690420 0.079 Uiso 1 1 calc R U . . .
H14C H 0.662893 0.489270 0.648087 0.079 Uiso 1 1 calc R U . . .
C15 C 0.6651(4) 0.2141(5) 0.0814(5) 0.0294(14) Uani 1 1 d . . . . .
H15 H 0.632081 0.225805 0.025128 0.035 Uiso 1 1 calc R U . . .
C16 C 0.6544(4) 0.0946(6) 0.1182(6) 0.0440(19) Uani 1 1 d . . . . .
H16A H 0.671347 0.040375 0.070367 0.066 Uiso 1 1 calc R U . . .
H16B H 0.601350 0.081709 0.131758 0.066 Uiso 1 1 calc R U . . .
H16C H 0.683593 0.084472 0.176213 0.066 Uiso 1 1 calc R U . . .
C17 C 0.7456(4) 0.2350(7) 0.0529(6) 0.0449(19) Uani 1 1 d . . . . .
H17A H 0.777933 0.227894 0.108494 0.067 Uiso 1 1 calc R U . . .
H17B H 0.750350 0.311254 0.026496 0.067 Uiso 1 1 calc R U . . .
H17C H 0.760598 0.179320 0.005187 0.067 Uiso 1 1 calc R U . . .
C18 C 0.6363(4) 0.4543(6) 0.1192(5) 0.0365(16) Uani 1 1 d . . . . .
H18 H 0.689154 0.475447 0.104405 0.044 Uiso 1 1 calc R U . . .
C19 C 0.5920(5) 0.4623(6) 0.0261(5) 0.058(2) Uani 1 1 d . . . . .
H19A H 0.539080 0.447072 0.038429 0.086 Uiso 1 1 calc R U . . .
H19B H 0.611365 0.406618 -0.019004 0.086 Uiso 1 1 calc R U . . .
H19C H 0.597458 0.538390 -0.000496 0.086 Uiso 1 1 calc R U . . .
C20 C 0.6083(4) 0.5378(6) 0.1915(6) 0.051(2) Uani 1 1 d . . . . .
H20A H 0.614570 0.614772 0.167282 0.076 Uiso 1 1 calc R U . . .
H20B H 0.636839 0.529124 0.250208 0.076 Uiso 1 1 calc R U . . .
H20C H 0.555232 0.523613 0.204088 0.076 Uiso 1 1 calc R U . . .
O3 O 0.4242(4) 0.1523(5) 0.8160(4) 0.0683(17) Uani 1 1 d . . . . .
C21 C 0.4369(5) 0.0456(8) 0.8541(6) 0.062(2) Uani 1 1 d . . . . .
H21A H 0.474107 0.004367 0.815395 0.074 Uiso 1 1 calc R U . . .
H21B H 0.389899 0.001490 0.854665 0.074 Uiso 1 1 calc R U . . .
C22 C 0.4654(5) 0.0601(8) 0.9527(6) 0.067(3) Uani 1 1 d . . . . .
H22A H 0.520424 0.051125 0.955225 0.080 Uiso 1 1 calc R U . . .
H22B H 0.442036 0.005019 0.996259 0.080 Uiso 1 1 calc R U . . .
C23 C 0.4429(5) 0.1784(9) 0.9768(6) 0.067(3) Uani 1 1 d . . . . .
H23A H 0.480099 0.214508 1.018906 0.080 Uiso 1 1 calc R U . . .
H23B H 0.393364 0.179881 1.007992 0.080 Uiso 1 1 calc R U . . .
C24 C 0.4401(5) 0.2372(7) 0.8813(6) 0.054(2) Uani 1 1 d . . . . .
H24A H 0.400679 0.295818 0.880626 0.065 Uiso 1 1 calc R U . . .
H24B H 0.488739 0.273243 0.866843 0.065 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 P1 2.1586(19) . ?
Cu1 N1 2.185(4) . ?
Cu1 Cl2 2.3282(17) . ?
Cu1 Cl1 2.3475(16) . ?
Cu1 Cu2 2.7224(9) . ?
Cu2 P2 2.1698(19) . ?
Cu2 N2 2.183(5) . ?
Cu2 Cl1 2.3482(17) . ?
Cu2 Cl2 2.3582(17) . ?
P1 O1 1.694(4) . ?
P1 C12 1.824(7) . ?
P1 C9 1.841(7) . ?
P2 O2 1.690(4) . ?
P2 C18 1.826(7) . ?
P2 C15 1.832(6) . ?
O1 C1 1.342(8) . ?
O2 C8 1.350(7) . ?
N1 C1 1.310(8) . ?
N1 C5 1.352(8) . ?
N2 C8 1.307(8) . ?
N2 C5 1.361(8) . ?
C1 C2 1.438(8) . ?
C2 C3 1.367(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.414(10) . ?
C3 H3 0.9500 . ?
C4 C6 1.408(10) . ?
C4 C5 1.416(7) . ?
C6 C7 1.346(10) . ?
C6 H6 0.9500 . ?
C7 C8 1.416(9) . ?
C7 H7 0.9500 . ?
C9 C11 1.516(9) . ?
C9 C10 1.523(9) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C14 1.519(11) . ?
C12 C13 1.539(9) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C17 1.516(9) . ?
C15 C16 1.520(10) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C20 1.507(10) . ?
C18 C19 1.540(10) . ?
C18 H18 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O3 C21 1.391(11) . ?
O3 C24 1.394(10) . ?
C21 C22 1.495(11) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.496(14) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.519(11) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?

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
P1 Cu1 N1 83.33(14) . . ?
P1 Cu1 Cl2 131.23(7) . . ?
N1 Cu1 Cl2 107.54(14) . . ?
P1 Cu1 Cl1 127.81(7) . . ?
N1 Cu1 Cl1 104.92(14) . . ?
Cl2 Cu1 Cl1 95.97(6) . . ?
P1 Cu1 Cu2 167.38(6) . . ?
N1 Cu1 Cu2 84.16(14) . . ?
Cl2 Cu1 Cu2 55.00(5) . . ?
Cl1 Cu1 Cu2 54.58(4) . . ?
P2 Cu2 N2 83.00(14) . . ?
P2 Cu2 Cl1 132.86(7) . . ?
N2 Cu2 Cl1 105.71(14) . . ?
P2 Cu2 Cl2 127.12(7) . . ?
N2 Cu2 Cl2 107.11(14) . . ?
Cl1 Cu2 Cl2 95.14(6) . . ?
P2 Cu2 Cu1 167.23(6) . . ?
N2 Cu2 Cu1 84.72(14) . . ?
Cl1 Cu2 Cu1 54.55(4) . . ?
Cl2 Cu2 Cu1 53.97(4) . . ?
Cu1 Cl1 Cu2 70.87(5) . . ?
Cu1 Cl2 Cu2 71.03(5) . . ?
O1 P1 C12 98.9(3) . . ?
O1 P1 C9 98.4(3) . . ?
C12 P1 C9 105.5(3) . . ?
O1 P1 Cu1 101.67(17) . . ?
C12 P1 Cu1 122.9(2) . . ?
C9 P1 Cu1 123.0(2) . . ?
O2 P2 C18 99.3(3) . . ?
O2 P2 C15 98.5(3) . . ?
C18 P2 C15 106.8(3) . . ?
O2 P2 Cu2 101.62(17) . . ?
C18 P2 Cu2 120.8(2) . . ?
C15 P2 Cu2 123.6(2) . . ?
C1 O1 P1 120.1(4) . . ?
C8 O2 P2 120.5(4) . . ?
C1 N1 C5 118.2(5) . . ?
C1 N1 Cu1 113.7(4) . . ?
C5 N1 Cu1 127.9(4) . . ?
C8 N2 C5 118.3(5) . . ?
C8 N2 Cu2 114.5(4) . . ?
C5 N2 Cu2 127.1(4) . . ?
N1 C1 O1 120.7(5) . . ?
N1 C1 C2 124.2(6) . . ?
O1 C1 C2 115.1(6) . . ?
C3 C2 C1 117.6(6) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 119.5(5) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C6 C4 C3 124.1(5) . . ?
C6 C4 C5 117.8(7) . . ?
C3 C4 C5 118.2(6) . . ?
N1 C5 N2 115.9(4) . . ?
N1 C5 C4 122.4(6) . . ?
N2 C5 C4 121.8(6) . . ?
C7 C6 C4 119.7(6) . . ?
C7 C6 H6 120.1 . . ?
C4 C6 H6 120.1 . . ?
C6 C7 C8 118.8(6) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
N2 C8 O2 120.2(5) . . ?
N2 C8 C7 123.6(6) . . ?
O2 C8 C7 116.2(5) . . ?
C11 C9 C10 111.2(6) . . ?
C11 C9 P1 114.8(5) . . ?
C10 C9 P1 108.4(4) . . ?
C11 C9 H9 107.4 . . ?
C10 C9 H9 107.4 . . ?
P1 C9 H9 107.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C12 C13 111.7(6) . . ?
C14 C12 P1 109.7(5) . . ?
C13 C12 P1 107.4(5) . . ?
C14 C12 H12 109.4 . . ?
C13 C12 H12 109.4 . . ?
P1 C12 H12 109.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C17 C15 C16 111.2(6) . . ?
C17 C15 P2 109.2(5) . . ?
C16 C15 P2 109.1(5) . . ?
C17 C15 H15 109.1 . . ?
C16 C15 H15 109.1 . . ?
P2 C15 H15 109.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C20 C18 C19 111.7(6) . . ?
C20 C18 P2 108.2(5) . . ?
C19 C18 P2 115.6(5) . . ?
C20 C18 H18 107.0 . . ?
C19 C18 H18 107.0 . . ?
P2 C18 H18 107.0 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 O3 C24 111.4(6) . . ?
O3 C21 C22 108.2(7) . . ?
O3 C21 H21A 110.1 . . ?
C22 C21 H21A 110.1 . . ?
O3 C21 H21B 110.1 . . ?
C22 C21 H21B 110.1 . . ?
H21A C21 H21B 108.4 . . ?
C21 C22 C23 103.2(8) . . ?
C21 C22 H22A 111.1 . . ?
C23 C22 H22A 111.1 . . ?
C21 C22 H22B 111.1 . . ?
C23 C22 H22B 111.1 . . ?
H22A C22 H22B 109.1 . . ?
C22 C23 C24 103.6(7) . . ?
C22 C23 H23A 111.0 . . ?
C24 C23 H23A 111.0 . . ?
C22 C23 H23B 111.0 . . ?
C24 C23 H23B 111.0 . . ?
H23A C23 H23B 109.0 . . ?
O3 C24 C23 105.4(7) . . ?
O3 C24 H24A 110.7 . . ?
C23 C24 H24A 110.7 . . ?
O3 C24 H24B 110.7 . . ?
C23 C24 H24B 110.7 . . ?
H24A C24 H24B 108.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 P1 O1 C1 132.5(5) . . . . ?
C9 P1 O1 C1 -120.2(5) . . . . ?
Cu1 P1 O1 C1 6.1(4) . . . . ?
C18 P2 O2 C8 -122.5(5) . . . . ?
C15 P2 O2 C8 128.7(4) . . . . ?
Cu2 P2 O2 C8 1.7(4) . . . . ?
C5 N1 C1 O1 -178.5(5) . . . . ?
Cu1 N1 C1 O1 6.2(7) . . . . ?
C5 N1 C1 C2 1.5(9) . . . . ?
Cu1 N1 C1 C2 -173.8(5) . . . . ?
P1 O1 C1 N1 -8.7(8) . . . . ?
P1 O1 C1 C2 171.3(4) . . . . ?
N1 C1 C2 C3 -1.7(9) . . . . ?
O1 C1 C2 C3 178.2(5) . . . . ?
C1 C2 C3 C4 0.5(8) . . . . ?
C2 C3 C4 C6 -179.2(6) . . . . ?
C2 C3 C4 C5 0.9(8) . . . . ?
C1 N1 C5 N2 -179.2(5) . . . . ?
Cu1 N1 C5 N2 -4.6(6) . . . . ?
C1 N1 C5 C4 0.1(8) . . . . ?
Cu1 N1 C5 C4 174.6(4) . . . . ?
C8 N2 C5 N1 -178.9(5) . . . . ?
Cu2 N2 C5 N1 5.4(6) . . . . ?
C8 N2 C5 C4 1.9(8) . . . . ?
Cu2 N2 C5 C4 -173.8(4) . . . . ?
C6 C4 C5 N1 178.9(5) . . . . ?
C3 C4 C5 N1 -1.2(8) . . . . ?
C6 C4 C5 N2 -2.0(8) . . . . ?
C3 C4 C5 N2 178.0(5) . . . . ?
C3 C4 C6 C7 -178.7(6) . . . . ?
C5 C4 C6 C7 1.3(8) . . . . ?
C4 C6 C7 C8 -0.5(9) . . . . ?
C5 N2 C8 O2 179.3(4) . . . . ?
Cu2 N2 C8 O2 -4.5(7) . . . . ?
C5 N2 C8 C7 -1.1(9) . . . . ?
Cu2 N2 C8 C7 175.1(5) . . . . ?
P2 O2 C8 N2 1.8(8) . . . . ?
P2 O2 C8 C7 -177.8(4) . . . . ?
C6 C7 C8 N2 0.5(9) . . . . ?
C6 C7 C8 O2 -180.0(5) . . . . ?
O1 P1 C9 C11 -57.4(5) . . . . ?
C12 P1 C9 C11 44.3(6) . . . . ?
Cu1 P1 C9 C11 -167.3(4) . . . . ?
O1 P1 C9 C10 67.6(5) . . . . ?
C12 P1 C9 C10 169.3(4) . . . . ?
Cu1 P1 C9 C10 -42.3(5) . . . . ?
O1 P1 C12 C14 -74.6(5) . . . . ?
C9 P1 C12 C14 -175.9(5) . . . . ?
Cu1 P1 C12 C14 35.6(6) . . . . ?
O1 P1 C12 C13 163.9(5) . . . . ?
C9 P1 C12 C13 62.5(5) . . . . ?
Cu1 P1 C12 C13 -85.9(5) . . . . ?
O2 P2 C15 C17 170.9(5) . . . . ?
C18 P2 C15 C17 68.4(6) . . . . ?
Cu2 P2 C15 C17 -79.0(5) . . . . ?
O2 P2 C15 C16 -67.4(5) . . . . ?
C18 P2 C15 C16 -169.9(5) . . . . ?
Cu2 P2 C15 C16 42.7(6) . . . . ?
O2 P2 C18 C20 73.3(5) . . . . ?
C15 P2 C18 C20 175.2(5) . . . . ?
Cu2 P2 C18 C20 -36.3(6) . . . . ?
O2 P2 C18 C19 -52.7(6) . . . . ?
C15 P2 C18 C19 49.2(7) . . . . ?
Cu2 P2 C18 C19 -162.3(5) . . . . ?
C24 O3 C21 C22 -1.4(10) . . . . ?
O3 C21 C22 C23 18.7(9) . . . . ?
C21 C22 C23 C24 -27.3(9) . . . . ?
C21 O3 C24 C23 -16.4(10) . . . . ?
C22 C23 C24 O3 27.4(10) . . . . ?

_refine_diff_density_max         1.019
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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_l1046a
_audit_block_doi                 10.5517/ccdc.csd.cc24tn7w
_database_code_depnum_ccdc_archive 'CCDC 1990858'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv.12023352 2020
loop_
_audit_author_name
_audit_author_address
'Martin Lutz'
;Utrecht University
Netherlands
;
_audit_update_record             
;
2020-03-17 deposited with the CCDC.	2020-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H38 Cl2 Ni O2 P2'
_chemical_formula_sum            'C16 H38 Cl2 Ni O2 P2'
_chemical_formula_weight         454.01

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'
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'

_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                   7.8506(7)
_cell_length_b                   8.2050(5)
_cell_length_c                   9.6512(8)
_cell_angle_alpha                111.818(4)
_cell_angle_beta                 100.304(3)
_cell_angle_gamma                97.698(3)
_cell_volume                     553.99(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6423
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.52

loop_
_diffrn_orient_matrix_type
_diffrn_orient_matrix_UB_11
_diffrn_orient_matrix_UB_12
_diffrn_orient_matrix_UB_13
_diffrn_orient_matrix_UB_21
_diffrn_orient_matrix_UB_22
_diffrn_orient_matrix_UB_23
_diffrn_orient_matrix_UB_31
_diffrn_orient_matrix_UB_32
_diffrn_orient_matrix_UB_33
'Nonius RMAT' -0.1262913 -0.0535334 -0.0601037 -0.0404825 0.0829427 0.0871744
0.0058039 0.0914616 -0.0453983
'Nonius RMAT' -0.1234087 -0.0629930 -0.0637760 -0.0489075 0.0774105 0.0838394
-0.0005985 0.0902776 -0.0466522

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             242
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.267
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5907
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   TWINABS-2012/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20918
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.347
_diffrn_reflns_theta_max         27.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2558
_reflns_number_gt                1938
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       Apex3
_computing_cell_refinement       Peakref
_computing_data_reduction        'Eval15, Twinabs'
_computing_structure_solution    'coordinates from Pd complex'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0553P)²+1.1977P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2558
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1351
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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
Ni1 Ni 0.000000 0.000000 0.000000 0.0180(2) Uani 1 2 d S . P . .
Cl1 Cl -0.01363(15) -0.15932(13) 0.13406(11) 0.0274(3) Uani 1 1 d . . . . .
P1 P 0.04342(13) -0.24008(13) -0.18671(11) 0.0174(2) Uani 1 1 d . . . . .
O1 O 0.1127(4) -0.2121(4) -0.3268(3) 0.0226(6) Uani 1 1 d . . . . .
C1 C -0.1691(5) -0.3931(5) -0.3044(4) 0.0217(8) Uani 1 1 d . . . . .
H1 H -0.147548 -0.478658 -0.401597 0.026 Uiso 1 1 calc R U . . .
C2 C -0.2942(6) -0.2815(6) -0.3484(5) 0.0279(9) Uani 1 1 d . . . . .
H2A H -0.402507 -0.362411 -0.423526 0.042 Uiso 1 1 calc R U . . .
H2B H -0.234871 -0.208267 -0.393540 0.042 Uiso 1 1 calc R U . . .
H2C H -0.324831 -0.202692 -0.256027 0.042 Uiso 1 1 calc R U . . .
C3 C -0.2536(6) -0.5041(6) -0.2285(5) 0.0285(10) Uani 1 1 d . . . . .
H3A H -0.270844 -0.423449 -0.130090 0.043 Uiso 1 1 calc R U . . .
H3B H -0.175776 -0.581768 -0.210105 0.043 Uiso 1 1 calc R U . . .
H3C H -0.368639 -0.578534 -0.296237 0.043 Uiso 1 1 calc R U . . .
C4 C 0.1846(6) -0.3770(5) -0.1277(4) 0.0210(8) Uani 1 1 d . . . . .
H4 H 0.119529 -0.436284 -0.072854 0.025 Uiso 1 1 calc R U . . .
C5 C 0.3598(6) -0.2588(6) -0.0135(5) 0.0283(9) Uani 1 1 d . . . . .
H5A H 0.428914 -0.333938 0.020764 0.042 Uiso 1 1 calc R U . . .
H5B H 0.334689 -0.167740 0.075730 0.042 Uiso 1 1 calc R U . . .
H5C H 0.427752 -0.199238 -0.063921 0.042 Uiso 1 1 calc R U . . .
C6 C 0.2177(6) -0.5265(6) -0.2659(5) 0.0271(9) Uani 1 1 d . . . . .
H6A H 0.289502 -0.472909 -0.317803 0.041 Uiso 1 1 calc R U . . .
H6B H 0.103902 -0.597826 -0.338032 0.041 Uiso 1 1 calc R U . . .
H6C H 0.280919 -0.604344 -0.230199 0.041 Uiso 1 1 calc R U . . .
C7 C 0.2780(6) -0.0890(6) -0.2976(5) 0.0273(9) Uani 1 1 d . . . . .
H7A H 0.377627 -0.150932 -0.295016 0.033 Uiso 1 1 calc R U . . .
H7B H 0.299689 0.013829 -0.196709 0.033 Uiso 1 1 calc R U . . .
C8 C 0.2657(7) -0.0228(6) -0.4242(5) 0.0346(11) Uani 1 1 d . . . . .
H8A H 0.239576 -0.125748 -0.523965 0.052 Uiso 1 1 calc R U . . .
H8B H 0.378807 0.056625 -0.408671 0.052 Uiso 1 1 calc R U . . .
H8C H 0.170777 0.043677 -0.422550 0.052 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 Cl1 2.1596(10) . ?
Ni1 Cl1 2.1596(10) 2 ?
Ni1 P1 2.2371(9) 2 ?
Ni1 P1 2.2371(9) . ?
P1 O1 1.624(3) . ?
P1 C1 1.831(4) . ?
P1 C4 1.843(4) . ?
O1 C7 1.446(5) . ?
C1 C3 1.521(6) . ?
C1 C2 1.537(6) . ?
C1 H1 1.0000 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C6 1.531(5) . ?
C4 C5 1.534(6) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.504(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
Cl1 Ni1 Cl1 180.00(3) . 2 ?
Cl1 Ni1 P1 92.33(4) . 2 ?
Cl1 Ni1 P1 87.67(4) 2 2 ?
Cl1 Ni1 P1 87.66(4) . . ?
Cl1 Ni1 P1 92.34(4) 2 . ?
P1 Ni1 P1 180.0 2 . ?
O1 P1 C1 96.64(16) . . ?
O1 P1 C4 105.05(17) . . ?
C1 P1 C4 106.59(18) . . ?
O1 P1 Ni1 118.34(11) . . ?
C1 P1 Ni1 110.41(13) . . ?
C4 P1 Ni1 117.36(12) . . ?
C7 O1 P1 121.1(2) . . ?
C3 C1 C2 111.2(3) . . ?
C3 C1 P1 114.3(3) . . ?
C2 C1 P1 108.0(3) . . ?
C3 C1 H1 107.7 . . ?
C2 C1 H1 107.7 . . ?
P1 C1 H1 107.7 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C6 C4 C5 111.2(3) . . ?
C6 C4 P1 112.2(3) . . ?
C5 C4 P1 111.2(3) . . ?
C6 C4 H4 107.3 . . ?
C5 C4 H4 107.3 . . ?
P1 C4 H4 107.3 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C8 108.5(4) . . ?
O1 C7 H7A 110.0 . . ?
C8 C7 H7A 110.0 . . ?
O1 C7 H7B 110.0 . . ?
C8 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 P1 O1 C7 176.1(3) . . . . ?
C4 P1 O1 C7 -74.7(3) . . . . ?
Ni1 P1 O1 C7 58.6(3) . . . . ?
O1 P1 C1 C3 160.5(3) . . . . ?
C4 P1 C1 C3 52.6(3) . . . . ?
Ni1 P1 C1 C3 -75.9(3) . . . . ?
O1 P1 C1 C2 -75.2(3) . . . . ?
C4 P1 C1 C2 176.9(3) . . . . ?
Ni1 P1 C1 C2 48.4(3) . . . . ?
O1 P1 C4 C6 -40.9(3) . . . . ?
C1 P1 C4 C6 60.9(3) . . . . ?
Ni1 P1 C4 C6 -174.8(2) . . . . ?
O1 P1 C4 C5 84.4(3) . . . . ?
C1 P1 C4 C5 -173.8(3) . . . . ?
Ni1 P1 C4 C5 -49.5(3) . . . . ?
P1 O1 C7 C8 -152.6(3) . . . . ?

_refine_diff_density_max         1.342
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.124

####################################################################### 
# 
# 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_l1049a
_audit_block_doi                 10.5517/ccdc.csd.cc24tn6v
_database_code_depnum_ccdc_archive 'CCDC 1990857'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv.12023352 2020
loop_
_audit_author_name
_audit_author_address
'Martin Lutz'
;Utrecht University
Netherlands
;
_audit_update_record             
;
2020-03-17 deposited with the CCDC.	2020-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H32 Br2 N2 Ni O2 P2, 1.5(C4 H8 O)'
_chemical_formula_sum            'C26 H44 Br2 N2 Ni O3.50 P2'
_chemical_formula_weight         721.10

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'
Br Br -0.2901 2.4595 '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'

_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                   8.2836(6)
_cell_length_b                   11.8373(9)
_cell_length_c                   16.2323(10)
_cell_angle_alpha                93.988(3)
_cell_angle_beta                 96.686(4)
_cell_angle_gamma                93.178(3)
_cell_volume                     1573.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    10956
_cell_measurement_theta_min      2.06
_cell_measurement_theta_max      27.61

loop_
_diffrn_orient_matrix_type
_diffrn_orient_matrix_UB_11
_diffrn_orient_matrix_UB_12
_diffrn_orient_matrix_UB_13
_diffrn_orient_matrix_UB_21
_diffrn_orient_matrix_UB_22
_diffrn_orient_matrix_UB_23
_diffrn_orient_matrix_UB_31
_diffrn_orient_matrix_UB_32
_diffrn_orient_matrix_UB_33
'Nonius RMAT' -0.1042098 0.0044133 -0.0370424 0.0608523 -0.0025568 -0.0495925
-0.0150118 -0.0846499 -0.0050395
'Nonius RMAT' -0.1093300 0.0023711 -0.0328497 0.0511463 -0.0065761 -0.0526858
-0.0148001 -0.0845148 -0.0014356

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_F_000             740
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    3.288
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4475
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   TWINABS-2012/1
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43550
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.728
_diffrn_reflns_theta_max         27.685
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7265
_reflns_number_gt                4666
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       Apex3
_computing_cell_refinement       Peakref
_computing_data_reduction        'Eval15, Twinabs'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0841P)²+0.4136P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7265
_refine_ls_number_parameters     407
_refine_ls_number_restraints     323
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1618
_refine_ls_wR_factor_gt          0.1392
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.052
_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
Br1 Br 0.84545(7) 0.56039(5) 0.33315(3) 0.05250(18) Uani 1 1 d . . . . .
Br2 Br 0.70506(8) 0.39916(6) 0.11335(3) 0.0632(2) Uani 1 1 d . . . . .
Ni1 Ni 0.59982(7) 0.42028(5) 0.23948(4) 0.03991(18) Uani 1 1 d . . . . .
P1 P 0.47681(17) 0.56480(11) 0.19640(8) 0.0452(3) Uani 1 1 d D . . . .
P2 P 0.66309(15) 0.25582(10) 0.28523(8) 0.0412(3) Uani 1 1 d D . . . .
O1 O 0.3802(4) 0.5992(3) 0.2792(2) 0.0502(9) Uani 1 1 d . . . . .
O2 O 0.6164(5) 0.0826(3) 0.4077(2) 0.0589(10) Uani 1 1 d . . . . .
N1 N 0.4657(5) 0.4317(3) 0.3264(2) 0.0371(9) Uani 1 1 d . . . . .
N2 N 0.5474(5) 0.2574(3) 0.3703(2) 0.0397(9) Uani 1 1 d . . . . .
C1 C 0.3778(6) 0.5228(4) 0.3368(3) 0.0418(11) Uani 1 1 d . . . . .
C2 C 0.2851(6) 0.5398(4) 0.4011(3) 0.0458(12) Uani 1 1 d . . . . .
H2 H 0.224869 0.604459 0.405655 0.055 Uiso 1 1 calc R U . . .
C3 C 0.2828(6) 0.4608(5) 0.4575(3) 0.0459(12) Uani 1 1 d . . . . .
H3 H 0.221466 0.471509 0.502343 0.055 Uiso 1 1 calc R U . . .
C4 C 0.3698(5) 0.3644(4) 0.4503(3) 0.0387(11) Uani 1 1 d . . . . .
C5 C 0.3694(6) 0.2753(5) 0.5057(3) 0.0473(12) Uani 1 1 d . . . . .
H5 H 0.312426 0.282497 0.552442 0.057 Uiso 1 1 calc R U . . .
C6 C 0.4491(6) 0.1820(4) 0.4917(3) 0.0499(13) Uani 1 1 d . . . . .
H6 H 0.443767 0.124208 0.528390 0.060 Uiso 1 1 calc R U . . .
C7 C 0.5430(6) 0.1660(4) 0.4228(3) 0.0454(12) Uani 1 1 d . . . . .
C8 C 0.4592(5) 0.3516(4) 0.3824(3) 0.0370(10) Uani 1 1 d . . . . .
C9 C 0.3073(6) 0.5402(4) 0.1129(3) 0.0566(14) Uani 1 1 d D . . . .
H9 H 0.353743 0.537804 0.059339 0.068 Uiso 1 1 calc R U . . .
C10 C 0.2175(8) 0.4255(5) 0.1181(5) 0.090(2) Uani 1 1 d D . . . .
H10A H 0.163126 0.427312 0.167963 0.135 Uiso 1 1 calc R U . . .
H10B H 0.294745 0.366837 0.120177 0.135 Uiso 1 1 calc R U . . .
H10C H 0.137354 0.409399 0.069586 0.135 Uiso 1 1 calc R U . . .
C11 C 0.1867(9) 0.6321(6) 0.1114(5) 0.098(3) Uani 1 1 d D . . . .
H11A H 0.113390 0.622014 0.059968 0.147 Uiso 1 1 calc R U . . .
H11B H 0.245102 0.705909 0.115218 0.147 Uiso 1 1 calc R U . . .
H11C H 0.124374 0.627053 0.158245 0.147 Uiso 1 1 calc R U . . .
C12 C 0.5938(7) 0.6977(4) 0.1844(3) 0.0588(15) Uani 1 1 d D . . . .
H12 H 0.702615 0.690653 0.215384 0.071 Uiso 1 1 calc R U . . .
C13 C 0.5302(10) 0.8026(5) 0.2244(5) 0.101(3) Uani 1 1 d D . . . .
H13A H 0.605055 0.867543 0.220716 0.152 Uiso 1 1 calc R U . . .
H13B H 0.520362 0.792107 0.282360 0.152 Uiso 1 1 calc R U . . .
H13C H 0.424167 0.815640 0.195708 0.152 Uiso 1 1 calc R U . . .
C14 C 0.6243(11) 0.7103(6) 0.0954(4) 0.114(3) Uani 1 1 d D . . . .
H14A H 0.521140 0.713565 0.060925 0.171 Uiso 1 1 calc R U . . .
H14B H 0.680288 0.645797 0.075637 0.171 Uiso 1 1 calc R U . . .
H14C H 0.691020 0.779559 0.092647 0.171 Uiso 1 1 calc R U . . .
C15 C 0.5760(7) 0.1263(5) 0.2219(3) 0.0592(15) Uani 1 1 d D . . . .
H15 H 0.574972 0.063616 0.259198 0.071 Uiso 1 1 calc R U . . .
C16 C 0.4018(7) 0.1409(6) 0.1872(5) 0.095(2) Uani 1 1 d D . . . .
H16A H 0.398496 0.203949 0.152086 0.143 Uiso 1 1 calc R U . . .
H16B H 0.337802 0.156128 0.232676 0.143 Uiso 1 1 calc R U . . .
H16C H 0.357287 0.072061 0.154687 0.143 Uiso 1 1 calc R U . . .
C17 C 0.6799(10) 0.0935(6) 0.1541(4) 0.096(3) Uani 1 1 d D . . . .
H17A H 0.631229 0.025210 0.122194 0.145 Uiso 1 1 calc R U . . .
H17B H 0.788465 0.079692 0.179083 0.145 Uiso 1 1 calc R U . . .
H17C H 0.686432 0.154657 0.117558 0.145 Uiso 1 1 calc R U . . .
C18 C 0.8715(6) 0.2263(4) 0.3298(3) 0.0519(13) Uani 1 1 d D . . . .
H18 H 0.877233 0.143092 0.330627 0.062 Uiso 1 1 calc R U . . .
C19 C 0.9141(6) 0.2790(5) 0.4184(3) 0.0627(16) Uani 1 1 d D . . . .
H19A H 1.025208 0.264036 0.438508 0.094 Uiso 1 1 calc R U . . .
H19B H 0.840442 0.246356 0.453868 0.094 Uiso 1 1 calc R U . . .
H19C H 0.903991 0.360348 0.419256 0.094 Uiso 1 1 calc R U . . .
C20 C 0.9942(7) 0.2696(6) 0.2743(4) 0.0682(17) Uani 1 1 d D . . . .
H20A H 0.983234 0.349907 0.268423 0.102 Uiso 1 1 calc R U . . .
H20B H 0.973754 0.228455 0.219895 0.102 Uiso 1 1 calc R U . . .
H20C H 1.103692 0.257961 0.299153 0.102 Uiso 1 1 calc R U . . .
O3A O 0.1068(16) 0.9637(13) 0.4078(7) 0.123(5) Uani 0.513(19) 1 d D U P A 1
C21A C -0.0475(17) 0.9073(17) 0.3744(8) 0.090(5) Uani 0.513(19) 1 d D U P A 1
H21A H -0.050364 0.826793 0.385158 0.108 Uiso 0.513(19) 1 calc R U P A 1
H21B H -0.136830 0.942485 0.399043 0.108 Uiso 0.513(19) 1 calc R U P A 1
C22A C -0.0590(17) 0.9203(17) 0.2899(8) 0.093(5) Uani 0.513(19) 1 d D U P A 1
H22A H -0.100308 0.848658 0.258720 0.111 Uiso 0.513(19) 1 calc R U P A 1
H22B H -0.135353 0.978262 0.275552 0.111 Uiso 0.513(19) 1 calc R U P A 1
C23A C 0.0915(19) 0.9521(18) 0.2690(7) 0.101(5) Uani 0.513(19) 1 d D U P A 1
H23A H 0.137273 0.887217 0.241246 0.121 Uiso 0.513(19) 1 calc R U P A 1
H23B H 0.082185 1.012342 0.230608 0.121 Uiso 0.513(19) 1 calc R U P A 1
C24A C 0.1912(18) 0.990(2) 0.3397(9) 0.113(6) Uani 0.513(19) 1 d D U P A 1
H24A H 0.215438 1.072188 0.340708 0.135 Uiso 0.513(19) 1 calc R U P A 1
H24B H 0.293931 0.952521 0.342266 0.135 Uiso 0.513(19) 1 calc R U P A 1
O3B O 0.098(3) 0.884(3) 0.4044(11) 0.219(9) Uani 0.487(19) 1 d D U P A 2
C21B C 0.221(2) 0.901(3) 0.3526(14) 0.146(8) Uani 0.487(19) 1 d D U P A 2
H21C H 0.277457 0.976613 0.366653 0.176 Uiso 0.487(19) 1 calc R U P A 2
H21D H 0.301594 0.843982 0.359355 0.176 Uiso 0.487(19) 1 calc R U P A 2
C22B C 0.146(3) 0.894(2) 0.2728(10) 0.130(7) Uani 0.487(19) 1 d D U P A 2
H22C H 0.161918 0.966238 0.248232 0.156 Uiso 0.487(19) 1 calc R U P A 2
H22D H 0.194283 0.835183 0.239360 0.156 Uiso 0.487(19) 1 calc R U P A 2
C23B C -0.014(2) 0.867(2) 0.2731(11) 0.121(7) Uani 0.487(19) 1 d D U P A 2
H23C H -0.039593 0.787565 0.252125 0.145 Uiso 0.487(19) 1 calc R U P A 2
H23D H -0.077582 0.914831 0.236406 0.145 Uiso 0.487(19) 1 calc R U P A 2
C24B C -0.054(3) 0.883(3) 0.3528(15) 0.166(9) Uani 0.487(19) 1 d D U P A 2
H24C H -0.129778 0.821426 0.364937 0.199 Uiso 0.487(19) 1 calc R U P A 2
H24D H -0.104709 0.955424 0.360871 0.199 Uiso 0.487(19) 1 calc R U P A 2
O4 O 0.056(3) 0.051(2) 0.0782(12) 0.224(8) Uani 0.5 1 d D U P B -3
C25 C 0.009(3) 0.1133(16) 0.0084(15) 0.160(7) Uani 0.5 1 d D U P B -3
H25A H -0.020943 0.189281 0.026122 0.192 Uiso 0.5 1 calc R U P B -3
H25B H 0.098156 0.120707 -0.026268 0.192 Uiso 0.5 1 calc R U P B -3
C26 C -0.122(2) 0.0500(17) -0.0343(12) 0.122(6) Uani 0.5 1 d D U P B -3
H26A H -0.118180 0.050421 -0.094338 0.146 Uiso 0.5 1 calc R U P B -3
H26B H -0.223838 0.082152 -0.021333 0.146 Uiso 0.5 1 calc R U P B -3
C27 C -0.117(3) -0.0592(17) -0.0105(15) 0.150(7) Uani 0.5 1 d D U P B -3
H27A H -0.112308 -0.112420 -0.059078 0.180 Uiso 0.5 1 calc R U P B -3
H27B H -0.215139 -0.080057 0.015010 0.180 Uiso 0.5 1 calc R U P B -3
C28 C 0.020(3) -0.064(2) 0.0459(16) 0.176(8) Uani 0.5 1 d D U P B -3
H28A H 0.110103 -0.092425 0.018429 0.212 Uiso 0.5 1 calc R U P B -3
H28B H -0.002174 -0.112285 0.090217 0.212 Uiso 0.5 1 calc R U P B -3


_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
Br1 Ni1 2.7852(8) . ?
Br2 Ni1 2.3200(8) . ?
Ni1 N1 1.897(4) . ?
Ni1 P1 2.1559(14) . ?
Ni1 P2 2.1999(13) . ?
P1 O1 1.681(4) . ?
P1 C9 1.831(5) . ?
P1 C12 1.835(5) . ?
P2 N2 1.770(4) . ?
P2 C15 1.848(6) . ?
P2 C18 1.854(5) . ?
O1 C1 1.346(5) . ?
O2 C7 1.214(6) . ?
N1 C1 1.346(6) . ?
N1 C8 1.361(5) . ?
N2 C8 1.382(6) . ?
N2 C7 1.425(6) . ?
C1 C2 1.376(7) . ?
C2 C3 1.355(7) . ?
C2 H2 0.9400 . ?
C3 C4 1.388(7) . ?
C3 H3 0.9400 . ?
C4 C8 1.402(6) . ?
C4 C5 1.434(7) . ?
C5 C6 1.338(7) . ?
C5 H5 0.9400 . ?
C6 C7 1.442(7) . ?
C6 H6 0.9400 . ?
C9 C11 1.517(6) . ?
C9 C10 1.523(6) . ?
C9 H9 0.9900 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 C13 1.511(6) . ?
C12 C14 1.511(6) . ?
C12 H12 0.9900 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 C16 1.510(6) . ?
C15 C17 1.517(6) . ?
C15 H15 0.9900 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C18 C19 1.521(6) . ?
C18 C20 1.526(5) . ?
C18 H18 0.9900 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
O3A C24A 1.417(10) . ?
O3A C21A 1.438(10) . ?
C21A C22A 1.384(9) . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C22A C23A 1.369(9) . ?
C22A H22A 0.9800 . ?
C22A H22B 0.9800 . ?
C23A C24A 1.367(9) . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C24A H24A 0.9800 . ?
C24A H24B 0.9800 . ?
O3B C21B 1.414(11) . ?
O3B C24B 1.432(11) . ?
C21B C22B 1.363(9) . ?
C21B H21C 0.9800 . ?
C21B H21D 0.9800 . ?
C22B C23B 1.349(9) . ?
C22B H22C 0.9800 . ?
C22B H22D 0.9800 . ?
C23B C24B 1.378(9) . ?
C23B H23C 0.9800 . ?
C23B H23D 0.9800 . ?
C24B H24C 0.9800 . ?
C24B H24D 0.9800 . ?
O4 C25 1.420(11) . ?
O4 C28 1.426(11) . ?
C25 C26 1.376(9) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C26 C27 1.376(9) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C27 C28 1.378(9) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ni1 P1 84.32(12) . . ?
N1 Ni1 P2 86.25(12) . . ?
P1 Ni1 P2 165.70(6) . . ?
N1 Ni1 Br2 166.38(12) . . ?
P1 Ni1 Br2 89.10(4) . . ?
P2 Ni1 Br2 97.77(4) . . ?
N1 Ni1 Br1 91.28(12) . . ?
P1 Ni1 Br1 91.45(4) . . ?
P2 Ni1 Br1 99.49(4) . . ?
Br2 Ni1 Br1 100.82(3) . . ?
O1 P1 C9 102.0(2) . . ?
O1 P1 C12 102.4(2) . . ?
C9 P1 C12 110.1(2) . . ?
O1 P1 Ni1 99.93(12) . . ?
C9 P1 Ni1 118.26(17) . . ?
C12 P1 Ni1 120.2(2) . . ?
N2 P2 C15 102.2(2) . . ?
N2 P2 C18 104.94(19) . . ?
C15 P2 C18 107.0(2) . . ?
N2 P2 Ni1 98.37(13) . . ?
C15 P2 Ni1 117.47(19) . . ?
C18 P2 Ni1 123.33(17) . . ?
C1 O1 P1 116.6(3) . . ?
C1 N1 C8 117.4(4) . . ?
C1 N1 Ni1 120.5(3) . . ?
C8 N1 Ni1 122.0(3) . . ?
C8 N2 C7 121.6(4) . . ?
C8 N2 P2 116.3(3) . . ?
C7 N2 P2 122.1(3) . . ?
O1 C1 N1 116.9(4) . . ?
O1 C1 C2 119.4(4) . . ?
N1 C1 C2 123.7(4) . . ?
C3 C2 C1 118.3(5) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.0(5) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C8 117.6(4) . . ?
C3 C4 C5 124.4(4) . . ?
C8 C4 C5 117.9(4) . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 122.9(4) . . ?
C5 C6 H6 118.5 . . ?
C7 C6 H6 118.5 . . ?
O2 C7 N2 119.4(4) . . ?
O2 C7 C6 125.0(4) . . ?
N2 C7 C6 115.6(5) . . ?
N1 C8 N2 117.0(4) . . ?
N1 C8 C4 121.9(4) . . ?
N2 C8 C4 121.1(4) . . ?
C11 C9 C10 109.4(5) . . ?
C11 C9 P1 113.9(4) . . ?
C10 C9 P1 110.5(4) . . ?
C11 C9 H9 107.6 . . ?
C10 C9 H9 107.6 . . ?
P1 C9 H9 107.6 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C14 112.9(5) . . ?
C13 C12 P1 114.7(4) . . ?
C14 C12 P1 112.4(4) . . ?
C13 C12 H12 105.3 . . ?
C14 C12 H12 105.3 . . ?
P1 C12 H12 105.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C17 112.0(5) . . ?
C16 C15 P2 110.4(4) . . ?
C17 C15 P2 111.5(4) . . ?
C16 C15 H15 107.6 . . ?
C17 C15 H15 107.6 . . ?
P2 C15 H15 107.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C20 110.4(5) . . ?
C19 C18 P2 112.2(3) . . ?
C20 C18 P2 109.5(4) . . ?
C19 C18 H18 108.2 . . ?
C20 C18 H18 108.2 . . ?
P2 C18 H18 108.2 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C24A O3A C21A 107.6(10) . . ?
C22A C21A O3A 104.6(8) . . ?
C22A C21A H21A 110.8 . . ?
O3A C21A H21A 110.8 . . ?
C22A C21A H21B 110.8 . . ?
O3A C21A H21B 110.8 . . ?
H21A C21A H21B 108.9 . . ?
C23A C22A C21A 109.4(8) . . ?
C23A C22A H22A 109.8 . . ?
C21A C22A H22A 109.8 . . ?
C23A C22A H22B 109.8 . . ?
C21A C22A H22B 109.8 . . ?
H22A C22A H22B 108.2 . . ?
C24A C23A C22A 109.0(8) . . ?
C24A C23A H23A 109.9 . . ?
C22A C23A H23A 109.9 . . ?
C24A C23A H23B 109.9 . . ?
C22A C23A H23B 109.9 . . ?
H23A C23A H23B 108.3 . . ?
C23A C24A O3A 106.8(8) . . ?
C23A C24A H24A 110.4 . . ?
O3A C24A H24A 110.4 . . ?
C23A C24A H24B 110.4 . . ?
O3A C24A H24B 110.4 . . ?
H24A C24A H24B 108.6 . . ?
C21B O3B C24B 106.7(12) . . ?
C22B C21B O3B 106.8(10) . . ?
C22B C21B H21C 110.4 . . ?
O3B C21B H21C 110.4 . . ?
C22B C21B H21D 110.4 . . ?
O3B C21B H21D 110.4 . . ?
H21C C21B H21D 108.6 . . ?
C23B C22B C21B 109.1(8) . . ?
C23B C22B H22C 109.9 . . ?
C21B C22B H22C 109.9 . . ?
C23B C22B H22D 109.9 . . ?
C21B C22B H22D 109.9 . . ?
H22C C22B H22D 108.3 . . ?
C22B C23B C24B 109.7(9) . . ?
C22B C23B H23C 109.7 . . ?
C24B C23B H23C 109.7 . . ?
C22B C23B H23D 109.7 . . ?
C24B C23B H23D 109.7 . . ?
H23C C23B H23D 108.2 . . ?
C23B C24B O3B 104.1(10) . . ?
C23B C24B H24C 110.9 . . ?
O3B C24B H24C 110.9 . . ?
C23B C24B H24D 110.9 . . ?
O3B C24B H24D 110.9 . . ?
H24C C24B H24D 109.0 . . ?
C25 O4 C28 102.8(15) . . ?
C26 C25 O4 104.4(10) . . ?
C26 C25 H25A 110.9 . . ?
O4 C25 H25A 110.9 . . ?
C26 C25 H25B 110.9 . . ?
O4 C25 H25B 110.9 . . ?
H25A C25 H25B 108.9 . . ?
C25 C26 C27 108.1(9) . . ?
C25 C26 H26A 110.1 . . ?
C27 C26 H26A 110.1 . . ?
C25 C26 H26B 110.1 . . ?
C27 C26 H26B 110.1 . . ?
H26A C26 H26B 108.4 . . ?
C26 C27 C28 107.7(9) . . ?
C26 C27 H27A 110.2 . . ?
C28 C27 H27A 110.2 . . ?
C26 C27 H27B 110.2 . . ?
C28 C27 H27B 110.2 . . ?
H27A C27 H27B 108.5 . . ?
C27 C28 O4 104.2(10) . . ?
C27 C28 H28A 110.9 . . ?
O4 C28 H28A 110.9 . . ?
C27 C28 H28B 110.9 . . ?
O4 C28 H28B 110.9 . . ?
H28A C28 H28B 108.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 P1 O1 C1 109.9(4) . . . . ?
C12 P1 O1 C1 -136.2(4) . . . . ?
Ni1 P1 O1 C1 -12.0(4) . . . . ?
P1 Ni1 N1 C1 -10.4(3) . . . . ?
P2 Ni1 N1 C1 -179.6(4) . . . . ?
Br2 Ni1 N1 C1 -71.8(7) . . . . ?
Br1 Ni1 N1 C1 81.0(4) . . . . ?
P1 Ni1 N1 C8 172.3(4) . . . . ?
P2 Ni1 N1 C8 3.1(3) . . . . ?
Br2 Ni1 N1 C8 110.9(5) . . . . ?
Br1 Ni1 N1 C8 -96.3(3) . . . . ?
C15 P2 N2 C8 -120.4(4) . . . . ?
C18 P2 N2 C8 128.0(4) . . . . ?
Ni1 P2 N2 C8 0.1(3) . . . . ?
C15 P2 N2 C7 58.6(4) . . . . ?
C18 P2 N2 C7 -53.0(4) . . . . ?
Ni1 P2 N2 C7 179.1(3) . . . . ?
P1 O1 C1 N1 6.1(6) . . . . ?
P1 O1 C1 C2 -172.5(4) . . . . ?
C8 N1 C1 O1 -177.5(4) . . . . ?
Ni1 N1 C1 O1 5.1(6) . . . . ?
C8 N1 C1 C2 1.1(7) . . . . ?
Ni1 N1 C1 C2 -176.3(4) . . . . ?
O1 C1 C2 C3 179.0(5) . . . . ?
N1 C1 C2 C3 0.5(8) . . . . ?
C1 C2 C3 C4 -0.9(8) . . . . ?
C2 C3 C4 C8 -0.2(7) . . . . ?
C2 C3 C4 C5 -177.8(5) . . . . ?
C3 C4 C5 C6 176.1(5) . . . . ?
C8 C4 C5 C6 -1.4(7) . . . . ?
C4 C5 C6 C7 1.8(8) . . . . ?
C8 N2 C7 O2 176.6(5) . . . . ?
P2 N2 C7 O2 -2.3(7) . . . . ?
C8 N2 C7 C6 -3.7(7) . . . . ?
P2 N2 C7 C6 177.4(3) . . . . ?
C5 C6 C7 O2 -179.6(5) . . . . ?
C5 C6 C7 N2 0.7(8) . . . . ?
C1 N1 C8 N2 178.8(4) . . . . ?
Ni1 N1 C8 N2 -3.8(6) . . . . ?
C1 N1 C8 C4 -2.3(7) . . . . ?
Ni1 N1 C8 C4 175.0(3) . . . . ?
C7 N2 C8 N1 -177.0(4) . . . . ?
P2 N2 C8 N1 2.0(5) . . . . ?
C7 N2 C8 C4 4.2(7) . . . . ?
P2 N2 C8 C4 -176.8(3) . . . . ?
C3 C4 C8 N1 1.9(7) . . . . ?
C5 C4 C8 N1 179.7(4) . . . . ?
C3 C4 C8 N2 -179.3(4) . . . . ?
C5 C4 C8 N2 -1.6(7) . . . . ?
O1 P1 C9 C11 47.2(5) . . . . ?
C12 P1 C9 C11 -60.9(5) . . . . ?
Ni1 P1 C9 C11 155.5(4) . . . . ?
O1 P1 C9 C10 -76.5(5) . . . . ?
C12 P1 C9 C10 175.4(4) . . . . ?
Ni1 P1 C9 C10 31.9(5) . . . . ?
O1 P1 C12 C13 -21.2(6) . . . . ?
C9 P1 C12 C13 86.7(6) . . . . ?
Ni1 P1 C12 C13 -130.6(5) . . . . ?
O1 P1 C12 C14 -151.9(5) . . . . ?
C9 P1 C12 C14 -44.0(6) . . . . ?
Ni1 P1 C12 C14 98.7(5) . . . . ?
N2 P2 C15 C16 66.7(5) . . . . ?
C18 P2 C15 C16 176.7(4) . . . . ?
Ni1 P2 C15 C16 -39.6(5) . . . . ?
N2 P2 C15 C17 -168.1(4) . . . . ?
C18 P2 C15 C17 -58.1(5) . . . . ?
Ni1 P2 C15 C17 85.7(5) . . . . ?
N2 P2 C18 C19 -34.1(4) . . . . ?
C15 P2 C18 C19 -142.1(4) . . . . ?
Ni1 P2 C18 C19 76.8(4) . . . . ?
N2 P2 C18 C20 -156.9(4) . . . . ?
C15 P2 C18 C20 95.1(4) . . . . ?
Ni1 P2 C18 C20 -46.1(4) . . . . ?
C24A O3A C21A C22A -10(2) . . . . ?
O3A C21A C22A C23A 16(2) . . . . ?
C21A C22A C23A C24A -16(2) . . . . ?
C22A C23A C24A O3A 10(2) . . . . ?
C21A O3A C24A C23A 0(2) . . . . ?
C24B O3B C21B C22B -9(4) . . . . ?
O3B C21B C22B C23B -3(3) . . . . ?
C21B C22B C23B C24B 14(3) . . . . ?
C22B C23B C24B O3B -19(3) . . . . ?
C21B O3B C24B C23B 17(4) . . . . ?
C28 O4 C25 C26 34(3) . . . . ?
O4 C25 C26 C27 -21(3) . . . . ?
C25 C26 C27 C28 -1(3) . . . . ?
C26 C27 C28 O4 22(3) . . . . ?
C25 O4 C28 C27 -34(3) . . . . ?

_refine_diff_density_max         0.853
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.115

