# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_1b_Ligand-ONP
_database_code_depnum_ccdc_archive 'CCDC 1585437'
_audit_update_record             
;
2017-11-14 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C19 H22 N O P'
_chemical_formula_moiety         'C19 H22 N O P'
_chemical_formula_weight         311.36
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   9.4204(9)
_cell_length_b                   9.3731(7)
_cell_length_c                   20.8127(15)
_cell_angle_alpha                90.0000
_cell_angle_beta                 98.482(8)
_cell_angle_gamma                90.0000
_cell_volume                     1817.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2719
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      28.40
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.025
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664.00
_exptl_absorpt_coefficient_mu    0.153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_T_max  0.996

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.629
_diffrn_reflns_number            13831
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.939
_diffrn_reflns_theta_full        25.242
_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
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4163
_reflns_number_gt                2053
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1356
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1371
_refine_ls_wR_factor_gt          0.1068
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         4163
_refine_ls_number_parameters     205
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0488P)²+0.0093P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.17
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
P P 0.1023 0.0942
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
P1 P 0.21566(7) 0.11539(6) 0.66694(3) 0.0586(2) Uani 1 1 d . . . . .
O1 O 0.0740(2) 0.65856(18) 0.48455(8) 0.0705(5) Uani 1 1 d . . . . .
N1 N 0.2446(3) 0.4545(2) 0.54482(10) 0.0625(6) Uani 1 1 d . . . . .
C1 C 0.4869(3) 0.5224(3) 0.59048(14) 0.0924(9) Uani 1 1 d . . . . .
H1A H 0.4766 0.4888 0.6336 0.111 Uiso 1 1 calc R U . . .
H1B H 0.5468 0.6070 0.5939 0.111 Uiso 1 1 calc R U . . .
H1C H 0.5312 0.4484 0.5675 0.111 Uiso 1 1 calc R U . . .
C2 C 0.3411(3) 0.5579(3) 0.55373(11) 0.0642(7) Uani 1 1 d . . . . .
C3 C 0.3131(3) 0.6932(3) 0.52979(13) 0.0703(7) Uani 1 1 d . . . . .
H3 H 0.3878 0.7604 0.5365 0.084 Uiso 1 1 calc R U . . .
C4 C 0.1801(3) 0.7381(3) 0.49597(12) 0.0650(7) Uani 1 1 d . . . . .
C5 C 0.1654(3) 0.8912(3) 0.47330(16) 0.1059(11) Uani 1 1 d . . . . .
H5A H 0.1027 0.8957 0.4320 0.127 Uiso 1 1 calc R U . . .
H5B H 0.2592 0.9285 0.4682 0.127 Uiso 1 1 calc R U . . .
H5C H 0.1249 0.9478 0.5051 0.127 Uiso 1 1 calc R U . . .
C6 C 0.2584(3) 0.3103(2) 0.57074(11) 0.0668(7) Uani 1 1 d . . . . .
H6A H 0.3596 0.2821 0.5768 0.080 Uiso 1 1 calc R U . . .
H6B H 0.2052 0.2444 0.5394 0.080 Uiso 1 1 calc R U . . .
C7 C 0.2012(3) 0.2987(2) 0.63546(11) 0.0604(7) Uani 1 1 d . . . . .
H7A H 0.1004 0.3287 0.6296 0.072 Uiso 1 1 calc R U . . .
H7B H 0.2557 0.3630 0.6671 0.072 Uiso 1 1 calc R U . . .
C8 C 0.4105(3) 0.1017(2) 0.68888(11) 0.0532(6) Uani 1 1 d . . . . .
C9 C 0.4839(3) 0.0079(3) 0.65433(13) 0.0747(8) Uani 1 1 d . . . . .
H9 H 0.4329 -0.0487 0.6214 0.090 Uiso 1 1 calc R U . . .
C10 C 0.6319(4) -0.0034(3) 0.66780(18) 0.0949(10) Uani 1 1 d . . . . .
H10 H 0.6806 -0.0667 0.6436 0.114 Uiso 1 1 calc R U . . .
C11 C 0.7076(4) 0.0766(3) 0.71577(19) 0.0910(10) Uani 1 1 d . . . . .
H11 H 0.8081 0.0689 0.7246 0.109 Uiso 1 1 calc R U . . .
C12 C 0.6363(3) 0.1678(3) 0.75080(15) 0.0824(9) Uani 1 1 d . . . . .
H12 H 0.6880 0.2224 0.7843 0.099 Uiso 1 1 calc R U . . .
C13 C 0.4885(3) 0.1808(3) 0.73758(13) 0.0672(7) Uani 1 1 d . . . . .
H13 H 0.4409 0.2444 0.7621 0.081 Uiso 1 1 calc R U . . .
C14 C 0.1584(2) 0.1373(2) 0.74668(11) 0.0526(6) Uani 1 1 d . . . . .
C15 C 0.0746(3) 0.2487(3) 0.76265(12) 0.0638(7) Uani 1 1 d . . . . .
H15 H 0.0488 0.3217 0.7322 0.077 Uiso 1 1 calc R U . . .
C16 C 0.0277(3) 0.2555(3) 0.82274(14) 0.0754(8) Uani 1 1 d . . . . .
H16 H -0.0279 0.3335 0.8328 0.091 Uiso 1 1 calc R U . . .
C17 C 0.0619(3) 0.1493(3) 0.86742(13) 0.0757(8) Uani 1 1 d . . . . .
H17 H 0.0297 0.1535 0.9080 0.091 Uiso 1 1 calc R U . . .
C18 C 0.1437(3) 0.0368(3) 0.85230(13) 0.0737(8) Uani 1 1 d . . . . .
H18 H 0.1678 -0.0367 0.8827 0.088 Uiso 1 1 calc R U . . .
C19 C 0.1908(3) 0.0306(3) 0.79268(12) 0.0643(7) Uani 1 1 d . . . . .
H19 H 0.2462 -0.0477 0.7830 0.077 Uiso 1 1 calc R U . . .
H1 H 0.159(3) 0.486(2) 0.5247(12) 0.079(9) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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
P1 C8 1.829(2) . ?
P1 C14 1.831(2) . ?
P1 C7 1.837(2) . ?
O1 C4 1.241(3) . ?
N1 C2 1.324(3) . ?
N1 C6 1.454(3) . ?
N1 H1 0.90(3) . ?
C1 C2 1.507(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.374(3) . ?
C3 C4 1.408(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.511(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C6 C7 1.526(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 C13 1.378(3) . ?
C8 C9 1.384(3) . ?
C9 C10 1.385(4) . ?
C9 H9 0.9400 . ?
C10 C11 1.363(4) . ?
C10 H10 0.9400 . ?
C11 C12 1.363(4) . ?
C11 H11 0.9400 . ?
C12 C13 1.384(3) . ?
C12 H12 0.9400 . ?
C13 H13 0.9400 . ?
C14 C15 1.379(3) . ?
C14 C19 1.387(3) . ?
C15 C16 1.388(3) . ?
C15 H15 0.9400 . ?
C16 C17 1.368(3) . ?
C16 H16 0.9400 . ?
C17 C18 1.370(3) . ?
C17 H17 0.9400 . ?
C18 C19 1.379(3) . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?

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
C8 P1 C14 101.56(11) . . ?
C8 P1 C7 100.00(11) . . ?
C14 P1 C7 101.66(10) . . ?
C2 N1 C6 127.4(2) . . ?
C2 N1 H1 112.3(15) . . ?
C6 N1 H1 119.8(15) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 122.3(3) . . ?
N1 C2 C1 117.7(3) . . ?
C3 C2 C1 120.0(3) . . ?
C2 C3 C4 124.5(3) . . ?
C2 C3 H3 117.7 . . ?
C4 C3 H3 117.7 . . ?
O1 C4 C3 123.2(2) . . ?
O1 C4 C5 118.5(3) . . ?
C3 C4 C5 118.3(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 . . ?
N1 C6 C7 111.69(19) . . ?
N1 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
N1 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 P1 111.33(16) . . ?
C6 C7 H7A 109.4 . . ?
P1 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
P1 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C13 C8 C9 118.1(3) . . ?
C13 C8 P1 123.54(19) . . ?
C9 C8 P1 118.4(2) . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.4(3) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C8 C13 C12 120.7(3) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C19 117.1(2) . . ?
C15 C14 P1 123.99(18) . . ?
C19 C14 P1 118.74(18) . . ?
C14 C15 C16 121.4(2) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 119.2(3) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C17 C18 C19 120.3(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 121.6(2) . . ?
C18 C19 H19 119.2 . . ?
C14 C19 H19 119.2 . . ?

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
C6 N1 C2 C3 -176.1(2) . . . . ?
C6 N1 C2 C1 5.0(4) . . . . ?
N1 C2 C3 C4 2.5(4) . . . . ?
C1 C2 C3 C4 -178.7(2) . . . . ?
C2 C3 C4 O1 0.2(4) . . . . ?
C2 C3 C4 C5 179.3(2) . . . . ?
C2 N1 C6 C7 92.2(3) . . . . ?
N1 C6 C7 P1 178.81(18) . . . . ?
C8 P1 C7 C6 70.29(19) . . . . ?
C14 P1 C7 C6 174.42(17) . . . . ?
C14 P1 C8 C13 -38.2(2) . . . . ?
C7 P1 C8 C13 66.0(2) . . . . ?
C14 P1 C8 C9 142.47(18) . . . . ?
C7 P1 C8 C9 -113.31(18) . . . . ?
C13 C8 C9 C10 -1.3(4) . . . . ?
P1 C8 C9 C10 178.1(2) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C9 C10 C11 C12 0.3(5) . . . . ?
C10 C11 C12 C13 -0.7(4) . . . . ?
C9 C8 C13 C12 0.8(3) . . . . ?
P1 C8 C13 C12 -178.49(18) . . . . ?
C11 C12 C13 C8 0.2(4) . . . . ?
C8 P1 C14 C15 125.3(2) . . . . ?
C7 P1 C14 C15 22.5(2) . . . . ?
C8 P1 C14 C19 -59.97(19) . . . . ?
C7 P1 C14 C19 -162.87(18) . . . . ?
C19 C14 C15 C16 1.5(4) . . . . ?
P1 C14 C15 C16 176.26(19) . . . . ?
C14 C15 C16 C17 -1.1(4) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C16 C17 C18 C19 -0.1(4) . . . . ?
C17 C18 C19 C14 0.5(4) . . . . ?
C15 C14 C19 C18 -1.2(4) . . . . ?
P1 C14 C19 C18 -176.2(2) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 . . . 2.687(3) 0.90(3) 1.94(2) 139(2) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_2c_Ni-NNN
_database_code_depnum_ccdc_archive 'CCDC 1585440'
_audit_update_record             
;
2017-11-14 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C20 H32 Cl N3 Ni'
_chemical_formula_moiety         'C20 H32 Cl N3 Ni'
_chemical_formula_weight         408.65
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   15.2771(10)
_cell_length_b                   10.0576(5)
_cell_length_c                   15.8197(10)
_cell_angle_alpha                90.0000
_cell_angle_beta                 115.809(8)
_cell_angle_gamma                90.0000
_cell_volume                     2188.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4954
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.40
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872.00
_exptl_absorpt_coefficient_mu    1.016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.732
_exptl_absorpt_correction_T_max  0.950

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.629
_diffrn_reflns_number            16353
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.549
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5014
_reflns_number_gt                3322
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.1020
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5014
_refine_ls_number_parameters     233
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0561P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.44
_refine_diff_density_min         -0.41
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Ni Ni 0.3393 1.1124
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.37307(2) 0.22665(4) 0.15742(2) 0.04371(13) Uani 1 1 d . . . . .
Cl1 Cl 0.41299(5) 0.10858(7) 0.28722(5) 0.0518(2) Uani 1 1 d . . . . .
N1 N 0.36694(15) 0.3582(2) 0.07244(15) 0.0480(5) Uani 1 1 d . . . . .
N2 N 0.24723(16) 0.2649(3) 0.14601(17) 0.0577(7) Uani 1 1 d . . . . .
N3 N 0.49279(15) 0.1645(2) 0.14865(15) 0.0464(5) Uani 1 1 d . . . . .
C1 C 0.3296(2) 0.5768(3) -0.0034(2) 0.0688(9) Uani 1 1 d . . . . .
H1A H 0.3945 0.6111 0.0341 0.083 Uiso 1 1 calc R U . . .
H1B H 0.2823 0.6469 -0.0140 0.083 Uiso 1 1 calc R U . . .
H1C H 0.3249 0.5457 -0.0632 0.083 Uiso 1 1 calc R U . . .
C2 C 0.3096(2) 0.4635(3) 0.04764(19) 0.0551(7) Uani 1 1 d . . . . .
C3 C 0.2289(2) 0.4721(3) 0.0658(2) 0.0692(9) Uani 1 1 d . . . . .
H3 H 0.1937 0.5522 0.0499 0.083 Uiso 1 1 calc R U . . .
C4 C 0.1954(2) 0.3735(4) 0.1050(2) 0.0701(9) Uani 1 1 d . . . . .
C5 C 0.0926(2) 0.3887(5) 0.0969(3) 0.1140(17) Uani 1 1 d . . . . .
H5A H 0.0918 0.3619 0.1555 0.137 Uiso 1 1 calc R U . . .
H5B H 0.0484 0.3329 0.0463 0.137 Uiso 1 1 calc R U . . .
H5C H 0.0724 0.4808 0.0838 0.137 Uiso 1 1 calc R U . . .
C6 C 0.4457(2) 0.3522(3) 0.0424(2) 0.0513(7) Uani 1 1 d . . . . .
H6A H 0.4986 0.4126 0.0804 0.062 Uiso 1 1 calc R U . . .
H6B H 0.4212 0.3781 -0.0237 0.062 Uiso 1 1 calc R U . . .
C7 C 0.4811(2) 0.2123(3) 0.0557(2) 0.0528(7) Uani 1 1 d . . . . .
H7A H 0.4344 0.1559 0.0059 0.063 Uiso 1 1 calc R U . . .
H7B H 0.5436 0.2076 0.0522 0.063 Uiso 1 1 calc R U . . .
C8 C 0.5069(2) 0.0169(3) 0.1530(2) 0.0586(8) Uani 1 1 d . . . . .
H8A H 0.5319 -0.0117 0.2186 0.070 Uiso 1 1 calc R U . . .
H8B H 0.5563 -0.0048 0.1313 0.070 Uiso 1 1 calc R U . . .
C9 C 0.4156(2) -0.0608(3) 0.0952(2) 0.0718(9) Uani 1 1 d . . . . .
H9A H 0.3668 -0.0421 0.1173 0.086 Uiso 1 1 calc R U . . .
H9B H 0.4302 -0.1551 0.1013 0.086 Uiso 1 1 calc R U . . .
H9C H 0.3911 -0.0350 0.0298 0.086 Uiso 1 1 calc R U . . .
C10 C 0.57985(19) 0.2288(3) 0.2260(2) 0.0562(7) Uani 1 1 d . . . . .
H10A H 0.5846 0.1961 0.2862 0.067 Uiso 1 1 calc R U . . .
H10B H 0.5680 0.3248 0.2239 0.067 Uiso 1 1 calc R U . . .
C11 C 0.6776(2) 0.2068(4) 0.2242(3) 0.0830(11) Uani 1 1 d . . . . .
H11A H 0.6756 0.2431 0.1666 0.100 Uiso 1 1 calc R U . . .
H11B H 0.6913 0.1123 0.2273 0.100 Uiso 1 1 calc R U . . .
H11C H 0.7282 0.2511 0.2777 0.100 Uiso 1 1 calc R U . . .
C12 C 0.19801(19) 0.1620(4) 0.1718(2) 0.0637(9) Uani 1 1 d . . . . .
C13 C 0.1564(2) 0.0571(4) 0.1094(2) 0.0760(10) Uani 1 1 d . . . . .
C14 C 0.1125(2) -0.0438(5) 0.1363(3) 0.0949(13) Uani 1 1 d . . . . .
H14 H 0.0847 -0.1152 0.0947 0.114 Uiso 1 1 calc R U . . .
C15 C 0.1075(2) -0.0446(5) 0.2210(3) 0.0986(15) Uani 1 1 d . . . . .
C16 C 0.1469(2) 0.0629(5) 0.2804(3) 0.0916(14) Uani 1 1 d . . . . .
H16 H 0.1422 0.0657 0.3376 0.110 Uiso 1 1 calc R U . . .
C17 C 0.1935(2) 0.1672(4) 0.2579(2) 0.0707(10) Uani 1 1 d . . . . .
C18 C 0.1561(2) 0.0568(5) 0.0143(2) 0.1022(14) Uani 1 1 d . . . . .
H18A H 0.1189 0.1321 -0.0218 0.123 Uiso 1 1 calc R U . . .
H18B H 0.1269 -0.0250 -0.0182 0.123 Uiso 1 1 calc R U . . .
H18C H 0.2224 0.0631 0.0216 0.123 Uiso 1 1 calc R U . . .
C19 C 0.0613(3) -0.1575(6) 0.2506(4) 0.154(2) Uani 1 1 d . . . . .
H19A H 0.0470 -0.2305 0.2064 0.185 Uiso 1 1 calc R U . . .
H19B H 0.0015 -0.1267 0.2514 0.185 Uiso 1 1 calc R U . . .
H19C H 0.1057 -0.1877 0.3128 0.185 Uiso 1 1 calc R U . . .
C20 C 0.2370(3) 0.2797(4) 0.3249(3) 0.0863(12) Uani 1 1 d . . . . .
H20A H 0.1956 0.3574 0.3025 0.104 Uiso 1 1 calc R U . . .
H20B H 0.3009 0.3000 0.3293 0.104 Uiso 1 1 calc R U . . .
H20C H 0.2427 0.2549 0.3863 0.104 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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 N1 1.860(2) . ?
Ni1 N2 1.891(2) . ?
Ni1 N3 1.994(2) . ?
Ni1 Cl1 2.2153(7) . ?
N1 C2 1.321(4) . ?
N1 C6 1.474(3) . ?
N2 C4 1.339(4) . ?
N2 C12 1.440(4) . ?
N3 C7 1.483(3) . ?
N3 C8 1.498(3) . ?
N3 C10 1.505(3) . ?
C1 C2 1.504(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.384(4) . ?
C3 C4 1.381(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.527(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C6 C7 1.490(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 C9 1.511(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 C11 1.521(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 C13 1.394(5) . ?
C12 C17 1.394(4) . ?
C13 C14 1.383(5) . ?
C13 C18 1.502(5) . ?
C14 C15 1.375(6) . ?
C14 H14 0.9400 . ?
C15 C16 1.387(6) . ?
C15 C19 1.515(5) . ?
C16 C17 1.398(5) . ?
C16 H16 0.9400 . ?
C17 C20 1.494(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?

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 N2 93.27(10) . . ?
N1 Ni1 N3 86.07(9) . . ?
N2 Ni1 N3 169.28(10) . . ?
N1 Ni1 Cl1 163.43(7) . . ?
N2 Ni1 Cl1 93.20(7) . . ?
N3 Ni1 Cl1 90.33(7) . . ?
C2 N1 C6 117.8(2) . . ?
C2 N1 Ni1 127.1(2) . . ?
C6 N1 Ni1 114.36(17) . . ?
C4 N2 C12 116.9(2) . . ?
C4 N2 Ni1 125.1(2) . . ?
C12 N2 Ni1 117.48(19) . . ?
C7 N3 C8 108.6(2) . . ?
C7 N3 C10 110.4(2) . . ?
C8 N3 C10 109.2(2) . . ?
C7 N3 Ni1 104.47(16) . . ?
C8 N3 Ni1 115.19(16) . . ?
C10 N3 Ni1 108.76(17) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 121.6(3) . . ?
N1 C2 C1 120.2(3) . . ?
C3 C2 C1 118.1(3) . . ?
C4 C3 C2 125.8(3) . . ?
C4 C3 H3 117.1 . . ?
C2 C3 H3 117.1 . . ?
N2 C4 C3 123.2(3) . . ?
N2 C4 C5 119.4(3) . . ?
C3 C4 C5 117.3(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 . . ?
N1 C6 C7 106.9(2) . . ?
N1 C6 H6A 110.3 . . ?
C7 C6 H6A 110.3 . . ?
N1 C6 H6B 110.3 . . ?
C7 C6 H6B 110.3 . . ?
H6A C6 H6B 108.6 . . ?
N3 C7 C6 109.0(2) . . ?
N3 C7 H7A 109.9 . . ?
C6 C7 H7A 109.9 . . ?
N3 C7 H7B 109.9 . . ?
C6 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
N3 C8 C9 114.1(2) . . ?
N3 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
N3 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 C11 116.7(3) . . ?
N3 C10 H10A 108.1 . . ?
C11 C10 H10A 108.1 . . ?
N3 C10 H10B 108.1 . . ?
C11 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 121.3(3) . . ?
C13 C12 N2 118.4(3) . . ?
C17 C12 N2 120.3(3) . . ?
C14 C13 C12 118.0(4) . . ?
C14 C13 C18 121.1(4) . . ?
C12 C13 C18 120.9(3) . . ?
C15 C14 C13 123.0(4) . . ?
C15 C14 H14 118.5 . . ?
C13 C14 H14 118.5 . . ?
C14 C15 C16 117.7(4) . . ?
C14 C15 C19 122.4(5) . . ?
C16 C15 C19 119.9(5) . . ?
C15 C16 C17 122.1(4) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C12 C17 C16 117.8(4) . . ?
C12 C17 C20 121.7(3) . . ?
C16 C17 C20 120.5(4) . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
N2 Ni1 N1 C2 21.3(2) . . . . ?
N3 Ni1 N1 C2 -169.4(2) . . . . ?
Cl1 Ni1 N1 C2 -91.6(3) . . . . ?
N2 Ni1 N1 C6 -168.86(18) . . . . ?
N3 Ni1 N1 C6 0.42(18) . . . . ?
Cl1 Ni1 N1 C6 78.3(3) . . . . ?
N1 Ni1 N2 C4 -13.0(3) . . . . ?
N3 Ni1 N2 C4 -99.1(6) . . . . ?
Cl1 Ni1 N2 C4 151.8(3) . . . . ?
N1 Ni1 N2 C12 158.3(2) . . . . ?
N3 Ni1 N2 C12 72.1(6) . . . . ?
Cl1 Ni1 N2 C12 -37.0(2) . . . . ?
C6 N1 C2 C3 174.3(3) . . . . ?
Ni1 N1 C2 C3 -16.1(4) . . . . ?
C6 N1 C2 C1 -4.4(4) . . . . ?
Ni1 N1 C2 C1 165.2(2) . . . . ?
N1 C2 C3 C4 -4.1(5) . . . . ?
C1 C2 C3 C4 174.6(3) . . . . ?
C12 N2 C4 C3 -171.4(3) . . . . ?
Ni1 N2 C4 C3 -0.1(5) . . . . ?
C12 N2 C4 C5 6.0(5) . . . . ?
Ni1 N2 C4 C5 177.3(3) . . . . ?
C2 C3 C4 N2 12.3(6) . . . . ?
C2 C3 C4 C5 -165.1(3) . . . . ?
C2 N1 C6 C7 -164.9(2) . . . . ?
Ni1 N1 C6 C7 24.2(3) . . . . ?
C8 N3 C7 C6 167.7(2) . . . . ?
C10 N3 C7 C6 -72.5(3) . . . . ?
Ni1 N3 C7 C6 44.3(2) . . . . ?
N1 C6 C7 N3 -45.1(3) . . . . ?
C7 N3 C8 C9 -73.6(3) . . . . ?
C10 N3 C8 C9 165.9(2) . . . . ?
Ni1 N3 C8 C9 43.2(3) . . . . ?
C7 N3 C10 C11 -58.9(3) . . . . ?
C8 N3 C10 C11 60.6(3) . . . . ?
Ni1 N3 C10 C11 -172.9(2) . . . . ?
C4 N2 C12 C13 94.9(4) . . . . ?
Ni1 N2 C12 C13 -77.0(3) . . . . ?
C4 N2 C12 C17 -85.8(4) . . . . ?
Ni1 N2 C12 C17 102.2(3) . . . . ?
C17 C12 C13 C14 -1.6(5) . . . . ?
N2 C12 C13 C14 177.6(3) . . . . ?
C17 C12 C13 C18 176.1(3) . . . . ?
N2 C12 C13 C18 -4.7(5) . . . . ?
C12 C13 C14 C15 0.5(6) . . . . ?
C18 C13 C14 C15 -177.2(4) . . . . ?
C13 C14 C15 C16 1.4(6) . . . . ?
C13 C14 C15 C19 -178.5(4) . . . . ?
C14 C15 C16 C17 -2.3(6) . . . . ?
C19 C15 C16 C17 177.6(3) . . . . ?
C13 C12 C17 C16 0.8(5) . . . . ?
N2 C12 C17 C16 -178.4(3) . . . . ?
C13 C12 C17 C20 -179.4(3) . . . . ?
N2 C12 C17 C20 1.3(4) . . . . ?
C15 C16 C17 C12 1.2(5) . . . . ?
C15 C16 C17 C20 -178.6(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_2b_Ni-ONP
_database_code_depnum_ccdc_archive 'CCDC 1585439'
_audit_update_record             
;
2017-11-14 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C19 H21 Cl N Ni O P'
_chemical_formula_moiety         'C19 H21 Cl N Ni O P'
_chemical_formula_weight         404.51
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.6206(2)
_cell_length_b                   11.6272(2)
_cell_length_c                   16.5733(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1853.90(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10177
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      29.98
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840.00
_exptl_absorpt_coefficient_mu    1.282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.742
_exptl_absorpt_correction_T_max  0.880

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.629
_diffrn_reflns_number            14071
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         3.019
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4232
_reflns_number_gt                4111
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.760
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.994

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0210
_refine_ls_wR_factor_ref         0.0550
_refine_ls_wR_factor_gt          0.0542
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4232
_refine_ls_number_parameters     219
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0297P)²+0.0987P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1723 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.015(5)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Ni Ni 0.3393 1.1124
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
P P 0.1023 0.0942
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.01769(3) 0.44140(2) 0.48909(2) 0.02605(8) Uani 1 1 d . . . . .
Cl1 Cl -0.06804(7) 0.54154(6) 0.58799(4) 0.04674(17) Uani 1 1 d . . . . .
P1 P 0.19290(6) 0.40676(5) 0.56372(3) 0.02769(13) Uani 1 1 d . . . . .
O1 O -0.13221(19) 0.48765(14) 0.42538(10) 0.0377(4) Uani 1 1 d . . . . .
N1 N 0.0972(2) 0.34325(17) 0.41027(11) 0.0328(4) Uani 1 1 d . . . . .
C1 C 0.1143(4) 0.2473(3) 0.27819(17) 0.0661(10) Uani 1 1 d . . . . .
H1A H 0.2082 0.2744 0.2684 0.079 Uiso 1 1 calc R U . . .
H1B H 0.0628 0.2468 0.2279 0.079 Uiso 1 1 calc R U . . .
H1C H 0.1176 0.1700 0.3001 0.079 Uiso 1 1 calc R U . . .
C2 C 0.0430(3) 0.3266(2) 0.33795(14) 0.0403(6) Uani 1 1 d . . . . .
C3 C -0.0813(3) 0.3769(2) 0.31125(14) 0.0452(7) Uani 1 1 d . . . . .
H3 H -0.1124 0.3567 0.2594 0.054 Uiso 1 1 calc R U . . .
C4 C -0.1614(3) 0.4529(2) 0.35397(14) 0.0383(5) Uani 1 1 d . . . . .
C5 C -0.2939(4) 0.5014(3) 0.31972(19) 0.0565(8) Uani 1 1 d . . . . .
H5A H -0.2896 0.5848 0.3205 0.068 Uiso 1 1 calc R U . . .
H5B H -0.3721 0.4757 0.3520 0.068 Uiso 1 1 calc R U . . .
H5C H -0.3054 0.4750 0.2646 0.068 Uiso 1 1 calc R U . . .
C6 C 0.2345(3) 0.2912(2) 0.42679(16) 0.0430(6) Uani 1 1 d . . . . .
H6A H 0.3078 0.3408 0.4050 0.052 Uiso 1 1 calc R U . . .
H6B H 0.2407 0.2163 0.3999 0.052 Uiso 1 1 calc R U . . .
C7 C 0.2559(3) 0.2759(2) 0.51677(16) 0.0405(6) Uani 1 1 d . . . . .
H7A H 0.3546 0.2644 0.5289 0.049 Uiso 1 1 calc R U . . .
H7B H 0.2036 0.2092 0.5364 0.049 Uiso 1 1 calc R U . . .
C8 C 0.1758(3) 0.3777(2) 0.67054(14) 0.0325(5) Uani 1 1 d . . . . .
C9 C 0.0731(3) 0.3018(3) 0.69540(16) 0.0456(7) Uani 1 1 d . . . . .
H9 H 0.0121 0.2698 0.6572 0.055 Uiso 1 1 calc R U . . .
C10 C 0.0602(4) 0.2732(3) 0.77565(18) 0.0557(8) Uani 1 1 d . . . . .
H10 H -0.0081 0.2203 0.7920 0.067 Uiso 1 1 calc R U . . .
C11 C 0.1480(4) 0.3225(3) 0.83227(17) 0.0583(9) Uani 1 1 d . . . . .
H11 H 0.1385 0.3039 0.8872 0.070 Uiso 1 1 calc R U . . .
C12 C 0.2479(4) 0.3978(3) 0.80822(17) 0.0619(10) Uani 1 1 d . . . . .
H12 H 0.3075 0.4306 0.8468 0.074 Uiso 1 1 calc R U . . .
C13 C 0.2630(3) 0.4268(3) 0.72748(14) 0.0467(7) Uani 1 1 d . . . . .
H13 H 0.3320 0.4793 0.7115 0.056 Uiso 1 1 calc R U . . .
C14 C 0.3270(3) 0.5150(2) 0.55562(13) 0.0334(5) Uani 1 1 d . . . . .
C15 C 0.2897(3) 0.6303(2) 0.56153(15) 0.0403(6) Uani 1 1 d . . . . .
H15 H 0.1957 0.6506 0.5676 0.048 Uiso 1 1 calc R U . . .
C16 C 0.3906(4) 0.7154(3) 0.55846(16) 0.0579(9) Uani 1 1 d . . . . .
H16 H 0.3651 0.7933 0.5624 0.069 Uiso 1 1 calc R U . . .
C17 C 0.5271(4) 0.6856(4) 0.54964(19) 0.0724(12) Uani 1 1 d . . . . .
H17 H 0.5955 0.7432 0.5486 0.087 Uiso 1 1 calc R U . . .
C18 C 0.5659(4) 0.5709(5) 0.5422(2) 0.0814(13) Uani 1 1 d . . . . .
H18 H 0.6599 0.5516 0.5346 0.098 Uiso 1 1 calc R U . . .
C19 C 0.4667(3) 0.4854(3) 0.5459(2) 0.0594(8) Uani 1 1 d . . . . .
H19 H 0.4929 0.4077 0.5419 0.071 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O1 1.8665(17) . ?
Ni1 N1 1.8959(19) . ?
Ni1 P1 2.1292(6) . ?
Ni1 Cl1 2.1732(6) . ?
P1 C14 1.807(3) . ?
P1 C8 1.810(2) . ?
P1 C7 1.813(2) . ?
O1 C4 1.282(3) . ?
N1 C2 1.321(3) . ?
N1 C6 1.478(3) . ?
C1 C2 1.517(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.403(4) . ?
C3 C4 1.369(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.505(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C6 C7 1.516(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 C13 1.385(4) . ?
C8 C9 1.387(4) . ?
C9 C10 1.377(4) . ?
C9 H9 0.9400 . ?
C10 C11 1.387(5) . ?
C10 H10 0.9400 . ?
C11 C12 1.360(5) . ?
C11 H11 0.9400 . ?
C12 C13 1.388(4) . ?
C12 H12 0.9400 . ?
C13 H13 0.9400 . ?
C14 C15 1.392(4) . ?
C14 C19 1.396(4) . ?
C15 C16 1.387(4) . ?
C15 H15 0.9400 . ?
C16 C17 1.366(6) . ?
C16 H16 0.9400 . ?
C17 C18 1.390(7) . ?
C17 H17 0.9400 . ?
C18 C19 1.380(5) . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 N1 95.48(8) . . ?
O1 Ni1 P1 174.16(6) . . ?
N1 Ni1 P1 88.10(6) . . ?
O1 Ni1 Cl1 88.80(6) . . ?
N1 Ni1 Cl1 174.50(6) . . ?
P1 Ni1 Cl1 87.92(2) . . ?
C14 P1 C8 105.50(11) . . ?
C14 P1 C7 108.28(13) . . ?
C8 P1 C7 107.08(11) . . ?
C14 P1 Ni1 112.99(8) . . ?
C8 P1 Ni1 122.12(9) . . ?
C7 P1 Ni1 100.02(9) . . ?
C4 O1 Ni1 126.94(17) . . ?
C2 N1 C6 117.4(2) . . ?
C2 N1 Ni1 123.64(18) . . ?
C6 N1 Ni1 118.64(15) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 124.1(2) . . ?
N1 C2 C1 120.2(3) . . ?
C3 C2 C1 115.7(2) . . ?
C4 C3 C2 125.9(2) . . ?
C4 C3 H3 117.1 . . ?
C2 C3 H3 117.1 . . ?
O1 C4 C3 123.9(2) . . ?
O1 C4 C5 114.6(3) . . ?
C3 C4 C5 121.6(2) . . ?
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 . . ?
N1 C6 C7 110.6(2) . . ?
N1 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C6 C7 P1 106.15(17) . . ?
C6 C7 H7A 110.5 . . ?
P1 C7 H7A 110.5 . . ?
C6 C7 H7B 110.5 . . ?
P1 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
C13 C8 C9 119.4(2) . . ?
C13 C8 P1 122.3(2) . . ?
C9 C8 P1 118.28(19) . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 119.9(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.9(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C8 C13 C12 119.6(3) . . ?
C8 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C19 119.6(3) . . ?
C15 C14 P1 118.8(2) . . ?
C19 C14 P1 121.6(2) . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 120.1(4) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 119.6(3) . . ?
C18 C19 H19 120.2 . . ?
C14 C19 H19 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Ni1 O1 C4 2.6(2) . . . . ?
Cl1 Ni1 O1 C4 -174.0(2) . . . . ?
O1 Ni1 N1 C2 -0.6(2) . . . . ?
P1 Ni1 N1 C2 -175.9(2) . . . . ?
O1 Ni1 N1 C6 173.05(18) . . . . ?
P1 Ni1 N1 C6 -2.32(17) . . . . ?
C6 N1 C2 C3 -175.3(2) . . . . ?
Ni1 N1 C2 C3 -1.6(4) . . . . ?
C6 N1 C2 C1 5.7(4) . . . . ?
Ni1 N1 C2 C1 179.4(2) . . . . ?
N1 C2 C3 C4 2.5(5) . . . . ?
C1 C2 C3 C4 -178.5(3) . . . . ?
Ni1 O1 C4 C3 -2.4(4) . . . . ?
Ni1 O1 C4 C5 176.87(18) . . . . ?
C2 C3 C4 O1 -0.3(5) . . . . ?
C2 C3 C4 C5 -179.6(3) . . . . ?
C2 N1 C6 C7 -157.3(2) . . . . ?
Ni1 N1 C6 C7 28.7(3) . . . . ?
N1 C6 C7 P1 -42.8(3) . . . . ?
C14 P1 C7 C6 -80.8(2) . . . . ?
C8 P1 C7 C6 165.83(19) . . . . ?
Ni1 P1 C7 C6 37.6(2) . . . . ?
C14 P1 C8 C13 -5.0(3) . . . . ?
C7 P1 C8 C13 110.2(2) . . . . ?
Ni1 P1 C8 C13 -135.8(2) . . . . ?
C14 P1 C8 C9 176.2(2) . . . . ?
C7 P1 C8 C9 -68.6(2) . . . . ?
Ni1 P1 C8 C9 45.5(2) . . . . ?
C13 C8 C9 C10 -1.6(4) . . . . ?
P1 C8 C9 C10 177.1(2) . . . . ?
C8 C9 C10 C11 1.5(5) . . . . ?
C9 C10 C11 C12 -0.9(5) . . . . ?
C10 C11 C12 C13 0.4(6) . . . . ?
C9 C8 C13 C12 1.1(4) . . . . ?
P1 C8 C13 C12 -177.6(2) . . . . ?
C11 C12 C13 C8 -0.5(5) . . . . ?
C8 P1 C14 C15 -87.2(2) . . . . ?
C7 P1 C14 C15 158.4(2) . . . . ?
Ni1 P1 C14 C15 48.6(2) . . . . ?
C8 P1 C14 C19 91.0(2) . . . . ?
C7 P1 C14 C19 -23.4(3) . . . . ?
Ni1 P1 C14 C19 -133.2(2) . . . . ?
C19 C14 C15 C16 -0.6(4) . . . . ?
P1 C14 C15 C16 177.70(19) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C15 C16 C17 C18 1.2(5) . . . . ?
C16 C17 C18 C19 -1.8(6) . . . . ?
C17 C18 C19 C14 1.2(6) . . . . ?
C15 C14 C19 C18 -0.1(5) . . . . ?
P1 C14 C19 C18 -178.3(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_2a_Ni-ONN
_database_code_depnum_ccdc_archive 'CCDC 1585438'
_audit_update_record             
;
2017-11-14 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C11 H21 Cl N2 Ni O'
_chemical_formula_moiety         'C11 H21 Cl N2 Ni O'
_chemical_formula_weight         291.45
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
_space_group_IT_number           29
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,1/2+Z
3 1/2-X,+Y,1/2+Z
4 1/2+X,-Y,+Z
#------------------------------------------------------------------------------
_cell_length_a                   11.6387(3)
_cell_length_b                   10.5076(2)
_cell_length_c                   10.8961(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1332.54(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6334
_cell_measurement_theta_min      3.98
_cell_measurement_theta_max      30.17
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616.00
_exptl_absorpt_coefficient_mu    1.639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.591
_exptl_absorpt_correction_T_max  0.721

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.629
_diffrn_reflns_number            9291
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         4.003
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_point_group_measured_fraction_full 0.867
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2591
_reflns_number_gt                2485
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.621
_reflns_Friedel_fraction_max     0.686
_reflns_Friedel_fraction_full    0.733

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0196
_refine_ls_wR_factor_ref         0.0530
_refine_ls_wR_factor_gt          0.0518
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2591
_refine_ls_number_parameters     149
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0336P)²+0.0824P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 912 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(11)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Ni Ni 0.3393 1.1124
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.18008(2) 0.24607(2) 0.47488(6) 0.02386(9) Uani 1 1 d . . . . .
Cl1 Cl 0.00730(4) 0.18426(6) 0.40672(6) 0.03491(14) Uani 1 1 d . . . . .
O1 O 0.16998(15) 0.38069(16) 0.36750(17) 0.0346(4) Uani 1 1 d . . . . .
N1 N 0.32737(15) 0.2906(2) 0.5283(2) 0.0273(4) Uani 1 1 d . . . . .
N2 N 0.19050(15) 0.09779(18) 0.58643(19) 0.0257(4) Uani 1 1 d . . . . .
C1 C 0.5016(2) 0.4189(3) 0.5589(3) 0.0468(7) Uani 1 1 d . . . . .
H1A H 0.5285 0.5028 0.5353 0.056 Uiso 1 1 calc R U . . .
H1B H 0.5549 0.3550 0.5292 0.056 Uiso 1 1 calc R U . . .
H1C H 0.4966 0.4139 0.6477 0.056 Uiso 1 1 calc R U . . .
C2 C 0.3843(2) 0.3958(2) 0.5039(2) 0.0312(5) Uani 1 1 d . . . . .
C3 C 0.3389(2) 0.4904(2) 0.4262(2) 0.0365(5) Uani 1 1 d . . . . .
H3 H 0.3796 0.5673 0.4187 0.044 Uiso 1 1 calc R U . . .
C4 C 0.2393(2) 0.4770(2) 0.3612(2) 0.0352(5) Uani 1 1 d . . . . .
C5 C 0.2030(3) 0.5789(3) 0.2720(3) 0.0566(9) Uani 1 1 d . . . . .
H5A H 0.2469 0.6558 0.2874 0.068 Uiso 1 1 calc R U . . .
H5B H 0.1218 0.5966 0.2824 0.068 Uiso 1 1 calc R U . . .
H5C H 0.2171 0.5500 0.1888 0.068 Uiso 1 1 calc R U . . .
C6 C 0.3844(2) 0.1877(2) 0.5964(3) 0.0346(5) Uani 1 1 d . . . . .
H6A H 0.4432 0.2223 0.6515 0.042 Uiso 1 1 calc R U . . .
H6B H 0.4211 0.1277 0.5398 0.042 Uiso 1 1 calc R U . . .
C7 C 0.2913(2) 0.1224(2) 0.6687(2) 0.0328(5) Uani 1 1 d . . . . .
H7A H 0.3202 0.0418 0.7018 0.039 Uiso 1 1 calc R U . . .
H7B H 0.2678 0.1763 0.7377 0.039 Uiso 1 1 calc R U . . .
C8 C 0.2114(2) -0.0156(2) 0.5069(2) 0.0344(5) Uani 1 1 d . . . . .
H8A H 0.2795 0.0014 0.4566 0.041 Uiso 1 1 calc R U . . .
H8B H 0.1460 -0.0246 0.4509 0.041 Uiso 1 1 calc R U . . .
C9 C 0.2291(2) -0.1426(2) 0.5722(3) 0.0435(6) Uani 1 1 d . . . . .
H9A H 0.2954 -0.1368 0.6259 0.052 Uiso 1 1 calc R U . . .
H9B H 0.2418 -0.2090 0.5118 0.052 Uiso 1 1 calc R U . . .
H9C H 0.1615 -0.1628 0.6204 0.052 Uiso 1 1 calc R U . . .
C10 C 0.0865(2) 0.0757(2) 0.6659(2) 0.0328(5) Uani 1 1 d . . . . .
H10A H 0.1061 0.0132 0.7293 0.039 Uiso 1 1 calc R U . . .
H10B H 0.0253 0.0391 0.6153 0.039 Uiso 1 1 calc R U . . .
C11 C 0.0414(3) 0.1945(3) 0.7275(3) 0.0426(6) Uani 1 1 d . . . . .
H11A H 0.1016 0.2322 0.7771 0.051 Uiso 1 1 calc R U . . .
H11B H -0.0234 0.1726 0.7794 0.051 Uiso 1 1 calc R U . . .
H11C H 0.0169 0.2549 0.6655 0.051 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O1 1.8394(18) . ?
Ni1 N1 1.8696(19) . ?
Ni1 N2 1.980(2) . ?
Ni1 Cl1 2.2399(6) . ?
O1 C4 1.297(3) . ?
N1 C2 1.316(3) . ?
N1 C6 1.470(3) . ?
N2 C8 1.494(3) . ?
N2 C7 1.499(3) . ?
N2 C10 1.506(3) . ?
C1 C2 1.511(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 H1C 0.9700 . ?
C2 C3 1.409(3) . ?
C3 C4 1.366(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.506(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C6 C7 1.505(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 C9 1.526(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 C11 1.511(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 N1 93.68(9) . . ?
O1 Ni1 N2 178.35(10) . . ?
N1 Ni1 N2 87.11(9) . . ?
O1 Ni1 Cl1 87.40(6) . . ?
N1 Ni1 Cl1 177.20(7) . . ?
N2 Ni1 Cl1 91.74(6) . . ?
C4 O1 Ni1 126.48(17) . . ?
C2 N1 C6 119.5(2) . . ?
C2 N1 Ni1 127.52(18) . . ?
C6 N1 Ni1 112.80(16) . . ?
C8 N2 C7 110.93(18) . . ?
C8 N2 C10 109.97(18) . . ?
C7 N2 C10 108.15(19) . . ?
C8 N2 Ni1 106.37(14) . . ?
C7 N2 Ni1 106.23(14) . . ?
C10 N2 Ni1 115.14(14) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 121.7(2) . . ?
N1 C2 C1 120.7(2) . . ?
C3 C2 C1 117.6(2) . . ?
C4 C3 C2 123.9(2) . . ?
C4 C3 H3 118.1 . . ?
C2 C3 H3 118.1 . . ?
O1 C4 C3 125.5(2) . . ?
O1 C4 C5 114.5(2) . . ?
C3 C4 C5 120.0(2) . . ?
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 . . ?
N1 C6 C7 105.9(2) . . ?
N1 C6 H6A 110.6 . . ?
C7 C6 H6A 110.6 . . ?
N1 C6 H6B 110.6 . . ?
C7 C6 H6B 110.6 . . ?
H6A C6 H6B 108.7 . . ?
N2 C7 C6 109.20(19) . . ?
N2 C7 H7A 109.8 . . ?
C6 C7 H7A 109.8 . . ?
N2 C7 H7B 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
N2 C8 C9 116.7(2) . . ?
N2 C8 H8A 108.1 . . ?
C9 C8 H8A 108.1 . . ?
N2 C8 H8B 108.1 . . ?
C9 C8 H8B 108.1 . . ?
H8A C8 H8B 107.3 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 C11 114.0(2) . . ?
N2 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
N2 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
N1 Ni1 O1 C4 -11.0(2) . . . . ?
Cl1 Ni1 O1 C4 171.5(2) . . . . ?
O1 Ni1 N1 C2 9.3(2) . . . . ?
N2 Ni1 N1 C2 -172.2(2) . . . . ?
O1 Ni1 N1 C6 -165.53(17) . . . . ?
N2 Ni1 N1 C6 13.02(18) . . . . ?
C6 N1 C2 C3 172.0(2) . . . . ?
Ni1 N1 C2 C3 -2.5(4) . . . . ?
C6 N1 C2 C1 -8.0(4) . . . . ?
Ni1 N1 C2 C1 177.56(19) . . . . ?
N1 C2 C3 C4 -6.4(4) . . . . ?
C1 C2 C3 C4 173.5(2) . . . . ?
Ni1 O1 C4 C3 6.3(4) . . . . ?
Ni1 O1 C4 C5 -174.46(18) . . . . ?
C2 C3 C4 O1 4.6(4) . . . . ?
C2 C3 C4 C5 -174.7(2) . . . . ?
C2 N1 C6 C7 148.8(2) . . . . ?
Ni1 N1 C6 C7 -36.0(2) . . . . ?
C8 N2 C7 C6 78.6(2) . . . . ?
C10 N2 C7 C6 -160.8(2) . . . . ?
Ni1 N2 C7 C6 -36.6(2) . . . . ?
N1 C6 C7 N2 47.0(3) . . . . ?
C7 N2 C8 C9 61.8(3) . . . . ?
C10 N2 C8 C9 -57.8(3) . . . . ?
Ni1 N2 C8 C9 176.90(19) . . . . ?
C8 N2 C10 C11 -166.4(2) . . . . ?
C7 N2 C10 C11 72.4(3) . . . . ?
Ni1 N2 C10 C11 -46.2(2) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


