# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1853541'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H18 N2'
_chemical_formula_sum            'C19 H18 N2'
_chemical_melting_point          ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         274.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   14.8246(15)
_cell_length_b                   13.5546(15)
_cell_length_c                   15.4910(16)
_cell_angle_alpha                90
_cell_angle_beta                 101.881(6)
_cell_angle_gamma                90
_cell_volume                     3046.1(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5585
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      29.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            54156
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.293
_diffrn_reflns_theta_max         29.101
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8139
_reflns_number_gt                5972
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0712P)²+0.1663P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8139
_refine_ls_number_parameters     391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1272
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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
N1A N 0.93422(6) 0.25719(7) 0.12224(6) 0.0216(2) Uani 1 1 d . . . . .
H1A H 0.9199(9) 0.2215(10) 0.1626(9) 0.028(4) Uiso 1 1 d . . . . .
N2A N 0.73009(6) 0.26818(7) 0.10011(6) 0.0229(2) Uani 1 1 d . . . . .
C2A C 0.87194(8) 0.28906(8) 0.04919(7) 0.0233(2) Uani 1 1 d . . . . .
C3A C 0.92147(8) 0.32735(9) -0.00930(8) 0.0290(3) Uani 1 1 d . . . . .
H3A H 0.8964 0.3548 -0.0655 0.035 Uiso 1 1 calc R U . . .
C4A C 1.01487(8) 0.31857(9) 0.02879(8) 0.0283(3) Uani 1 1 d . . . . .
H4A H 1.0648 0.3392 0.0033 0.034 Uiso 1 1 calc R U . . .
C5A C 1.02179(8) 0.27431(8) 0.11046(8) 0.0224(2) Uani 1 1 d . . . . .
C6A C 0.77390(8) 0.29049(8) 0.04001(7) 0.0236(2) Uani 1 1 d . . . . .
H6A H 0.7383 0.3097 -0.0157 0.028 Uiso 1 1 calc R U . . .
C7A C 1.10454(8) 0.25562(8) 0.17796(8) 0.0240(2) Uani 1 1 d . . . . .
C8A C 1.18949(9) 0.24239(10) 0.15368(9) 0.0324(3) Uani 1 1 d . . . . .
H8A H 1.1921 0.2398 0.0930 0.039 Uiso 1 1 calc R U . . .
C9A C 1.26955(9) 0.23303(11) 0.21679(10) 0.0385(3) Uani 1 1 d . . . . .
H9A H 1.3270 0.2254 0.1993 0.046 Uiso 1 1 calc R U . . .
C10A C 1.26643(9) 0.23477(11) 0.30550(10) 0.0393(3) Uani 1 1 d . . . . .
H10A H 1.3215 0.2276 0.3490 0.047 Uiso 1 1 calc R U . . .
C11A C 1.18290(9) 0.24700(10) 0.33034(9) 0.0363(3) Uani 1 1 d . . . . .
H11A H 1.1806 0.2481 0.3912 0.044 Uiso 1 1 calc R U . . .
C12A C 1.10236(8) 0.25773(9) 0.26736(8) 0.0284(3) Uani 1 1 d . . . . .
H12A H 1.0453 0.2666 0.2853 0.034 Uiso 1 1 calc R U . . .
C13A C 0.63230(8) 0.28133(9) 0.07927(7) 0.0224(2) Uani 1 1 d . . . . .
C14A C 0.57546(8) 0.19810(9) 0.06172(7) 0.0244(2) Uani 1 1 d . . . . .
C15A C 0.48040(9) 0.21136(10) 0.04725(8) 0.0304(3) Uani 1 1 d . . . . .
H15A H 0.4408 0.1558 0.0349 0.037 Uiso 1 1 calc R U . . .
C16A C 0.44287(9) 0.30441(11) 0.05067(9) 0.0340(3) Uani 1 1 d . . . . .
H16A H 0.3779 0.3123 0.0415 0.041 Uiso 1 1 calc R U . . .
C17A C 0.50012(9) 0.38619(10) 0.06746(8) 0.0313(3) Uani 1 1 d . . . . .
H17A H 0.4738 0.4498 0.0697 0.038 Uiso 1 1 calc R U . . .
C18A C 0.59529(8) 0.37656(9) 0.08098(7) 0.0257(2) Uani 1 1 d . . . . .
C19A C 0.61599(8) 0.09739(9) 0.05517(8) 0.0291(3) Uani 1 1 d . . . . .
H19D H 0.6441 0.0947 0.0032 0.044 Uiso 1 1 calc R U . . .
H19E H 0.5672 0.0476 0.0497 0.044 Uiso 1 1 calc R U . . .
H19F H 0.6631 0.0843 0.1083 0.044 Uiso 1 1 calc R U . . .
C20A C 0.65591(9) 0.46657(9) 0.09588(9) 0.0320(3) Uani 1 1 d . . . . .
H20D H 0.6811 0.4793 0.0432 0.048 Uiso 1 1 calc R U . . .
H20E H 0.7066 0.4555 0.1466 0.048 Uiso 1 1 calc R U . . .
H20F H 0.6195 0.5235 0.1076 0.048 Uiso 1 1 calc R U . . .
N1B N 0.72643(6) 0.17226(7) 0.27540(6) 0.0198(2) Uani 1 1 d . . . . .
H1B H 0.7443(10) 0.2087(11) 0.2360(10) 0.033(4) Uiso 1 1 d . . . . .
N2B N 0.87815(6) 0.07107(7) 0.21849(6) 0.0237(2) Uani 1 1 d . . . . .
C2B C 0.74867(8) 0.07412(8) 0.28899(7) 0.0220(2) Uani 1 1 d . . . . .
C3B C 0.68720(8) 0.03291(9) 0.33490(8) 0.0258(2) Uani 1 1 d . . . . .
H3B H 0.6864 -0.0337 0.3539 0.031 Uiso 1 1 calc R U . . .
C4B C 0.62614(8) 0.10792(9) 0.34824(8) 0.0241(2) Uani 1 1 d . . . . .
H4B H 0.5766 0.1012 0.3782 0.029 Uiso 1 1 calc R U . . .
C5B C 0.65082(7) 0.19331(8) 0.31013(7) 0.0193(2) Uani 1 1 d . . . . .
C6B C 0.82231(8) 0.02626(8) 0.25798(7) 0.0226(2) Uani 1 1 d . . . . .
H6B H 0.8301 -0.0428 0.2673 0.027 Uiso 1 1 calc R U . . .
C7B C 0.61223(7) 0.29263(8) 0.30973(7) 0.0205(2) Uani 1 1 d . . . . .
C8B C 0.51956(8) 0.30554(10) 0.31286(8) 0.0296(3) Uani 1 1 d . . . . .
H8B H 0.4814 0.2495 0.3143 0.036 Uiso 1 1 calc R U . . .
C9B C 0.48288(9) 0.39911(11) 0.31387(9) 0.0367(3) Uani 1 1 d . . . . .
H9B H 0.4195 0.4069 0.3154 0.044 Uiso 1 1 calc R U . . .
C10B C 0.53758(10) 0.48173(10) 0.31264(8) 0.0358(3) Uani 1 1 d . . . . .
H10B H 0.5119 0.5459 0.3131 0.043 Uiso 1 1 calc R U . . .
C11B C 0.62947(10) 0.47019(10) 0.31073(9) 0.0341(3) Uani 1 1 d . . . . .
H11B H 0.6675 0.5265 0.3104 0.041 Uiso 1 1 calc R U . . .
C12B C 0.66653(8) 0.37619(9) 0.30931(8) 0.0279(3) Uani 1 1 d . . . . .
H12B H 0.7300 0.3689 0.3080 0.033 Uiso 1 1 calc R U . . .
C13B C 0.94585(8) 0.00981(8) 0.19111(7) 0.0230(2) Uani 1 1 d . . . . .
C14B C 0.92803(8) -0.02729(9) 0.10478(8) 0.0278(3) Uani 1 1 d . . . . .
C15B C 0.99414(9) -0.08663(10) 0.07923(9) 0.0342(3) Uani 1 1 d . . . . .
H15B H 0.9832 -0.1123 0.0209 0.041 Uiso 1 1 calc R U . . .
C16B C 1.07547(9) -0.10904(11) 0.13699(9) 0.0363(3) Uani 1 1 d . . . . .
H16B H 1.1197 -0.1505 0.1187 0.044 Uiso 1 1 calc R U . . .
C17B C 1.09239(8) -0.07086(10) 0.22163(9) 0.0311(3) Uani 1 1 d . . . . .
H17B H 1.1489 -0.0858 0.2609 0.037 Uiso 1 1 calc R U . . .
C18B C 1.02833(8) -0.01100(8) 0.25035(8) 0.0240(2) Uani 1 1 d . . . . .
C19B C 0.83823(9) -0.00552(11) 0.04261(9) 0.0363(3) Uani 1 1 d . . . . .
H19A H 0.8411 -0.0290 -0.0166 0.054 Uiso 1 1 calc R U . . .
H19B H 0.8271 0.0658 0.0409 0.054 Uiso 1 1 calc R U . . .
H19C H 0.7880 -0.0392 0.0631 0.054 Uiso 1 1 calc R U . . .
C20B C 1.04574(9) 0.02749(10) 0.34333(8) 0.0295(3) Uani 1 1 d . . . . .
H20A H 1.0115 -0.0124 0.3784 0.044 Uiso 1 1 calc R U . . .
H20B H 1.0253 0.0963 0.3430 0.044 Uiso 1 1 calc R U . . .
H20C H 1.1118 0.0237 0.3692 0.044 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
N1A C5A 1.3673(14) . ?
N1A C2A 1.3744(14) . ?
N1A H1A 0.851(15) . ?
N2A C6A 1.2763(15) . ?
N2A C13A 1.4301(14) . ?
C2A C3A 1.3797(16) . ?
C2A C6A 1.4310(16) . ?
C3A C4A 1.3940(17) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.3849(16) . ?
C4A H4A 0.9500 . ?
C5A C7A 1.4610(16) . ?
C6A H6A 0.9500 . ?
C7A C12A 1.3922(17) . ?
C7A C8A 1.3981(17) . ?
C8A C9A 1.3793(19) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.385(2) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.380(2) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.3852(18) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
C13A C14A 1.4008(16) . ?
C13A C18A 1.4049(16) . ?
C14A C15A 1.3924(16) . ?
C14A C19A 1.5032(16) . ?
C15A C16A 1.3839(19) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.3877(19) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.3892(17) . ?
C17A H17A 0.9500 . ?
C18A C20A 1.5047(18) . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 0.9800 . ?
N1B C5B 1.3695(14) . ?
N1B C2B 1.3763(14) . ?
N1B H1B 0.868(15) . ?
N2B C6B 1.2795(15) . ?
N2B C13B 1.4324(14) . ?
C2B C3B 1.3839(16) . ?
C2B C6B 1.4350(15) . ?
C3B C4B 1.4045(16) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.3824(16) . ?
C4B H4B 0.9500 . ?
C5B C7B 1.4623(15) . ?
C6B H6B 0.9500 . ?
C7B C12B 1.3903(16) . ?
C7B C8B 1.3956(16) . ?
C8B C9B 1.3813(18) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.385(2) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.3775(19) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.3895(17) . ?
C11B H11B 0.9500 . ?
C12B H12B 0.9500 . ?
C13B C18B 1.3982(16) . ?
C13B C14B 1.4020(16) . ?
C14B C15B 1.3870(17) . ?
C14B C19B 1.5030(17) . ?
C15B C16B 1.3793(18) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.3836(18) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.3900(16) . ?
C17B H17B 0.9500 . ?
C18B C20B 1.5034(17) . ?
C19B H19A 0.9800 . ?
C19B H19B 0.9800 . ?
C19B H19C 0.9800 . ?
C20B H20A 0.9800 . ?
C20B H20B 0.9800 . ?
C20B H20C 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
C5A N1A C2A 109.40(10) . . ?
C5A N1A H1A 125.5(9) . . ?
C2A N1A H1A 123.8(9) . . ?
C6A N2A C13A 116.76(9) . . ?
N1A C2A C3A 107.50(10) . . ?
N1A C2A C6A 125.62(10) . . ?
C3A C2A C6A 126.62(11) . . ?
C2A C3A C4A 107.85(11) . . ?
C2A C3A H3A 126.1 . . ?
C4A C3A H3A 126.1 . . ?
C5A C4A C3A 107.69(10) . . ?
C5A C4A H4A 126.2 . . ?
C3A C4A H4A 126.2 . . ?
N1A C5A C4A 107.55(10) . . ?
N1A C5A C7A 123.74(10) . . ?
C4A C5A C7A 128.49(11) . . ?
N2A C6A C2A 125.67(11) . . ?
N2A C6A H6A 117.2 . . ?
C2A C6A H6A 117.2 . . ?
C12A C7A C8A 118.49(11) . . ?
C12A C7A C5A 121.35(11) . . ?
C8A C7A C5A 119.99(11) . . ?
C9A C8A C7A 120.83(13) . . ?
C9A C8A H8A 119.6 . . ?
C7A C8A H8A 119.6 . . ?
C8A C9A C10A 120.14(13) . . ?
C8A C9A H9A 119.9 . . ?
C10A C9A H9A 119.9 . . ?
C11A C10A C9A 119.60(12) . . ?
C11A C10A H10A 120.2 . . ?
C9A C10A H10A 120.2 . . ?
C10A C11A C12A 120.60(13) . . ?
C10A C11A H11A 119.7 . . ?
C12A C11A H11A 119.7 . . ?
C11A C12A C7A 120.35(12) . . ?
C11A C12A H12A 119.8 . . ?
C7A C12A H12A 119.8 . . ?
C14A C13A C18A 121.47(11) . . ?
C14A C13A N2A 118.99(10) . . ?
C18A C13A N2A 119.47(10) . . ?
C15A C14A C13A 118.40(11) . . ?
C15A C14A C19A 120.78(11) . . ?
C13A C14A C19A 120.77(10) . . ?
C16A C15A C14A 120.87(12) . . ?
C16A C15A H15A 119.6 . . ?
C14A C15A H15A 119.6 . . ?
C15A C16A C17A 120.00(12) . . ?
C15A C16A H16A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C16A C17A C18A 121.07(12) . . ?
C16A C17A H17A 119.5 . . ?
C18A C17A H17A 119.5 . . ?
C17A C18A C13A 118.16(11) . . ?
C17A C18A C20A 120.19(11) . . ?
C13A C18A C20A 121.65(11) . . ?
C14A C19A H19D 109.5 . . ?
C14A C19A H19E 109.5 . . ?
H19D C19A H19E 109.5 . . ?
C14A C19A H19F 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C18A C20A H20D 109.5 . . ?
C18A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
C18A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C5B N1B C2B 109.33(9) . . ?
C5B N1B H1B 123.4(10) . . ?
C2B N1B H1B 124.0(10) . . ?
C6B N2B C13B 115.35(10) . . ?
N1B C2B C3B 107.84(10) . . ?
N1B C2B C6B 124.09(10) . . ?
C3B C2B C6B 128.06(11) . . ?
C2B C3B C4B 107.22(10) . . ?
C2B C3B H3B 126.4 . . ?
C4B C3B H3B 126.4 . . ?
C5B C4B C3B 107.94(10) . . ?
C5B C4B H4B 126.0 . . ?
C3B C4B H4B 126.0 . . ?
N1B C5B C4B 107.65(10) . . ?
N1B C5B C7B 122.77(10) . . ?
C4B C5B C7B 129.42(10) . . ?
N2B C6B C2B 123.87(11) . . ?
N2B C6B H6B 118.1 . . ?
C2B C6B H6B 118.1 . . ?
C12B C7B C8B 118.23(11) . . ?
C12B C7B C5B 121.58(10) . . ?
C8B C7B C5B 120.15(10) . . ?
C9B C8B C7B 120.54(12) . . ?
C9B C8B H8B 119.7 . . ?
C7B C8B H8B 119.7 . . ?
C8B C9B C10B 120.61(12) . . ?
C8B C9B H9B 119.7 . . ?
C10B C9B H9B 119.7 . . ?
C11B C10B C9B 119.53(12) . . ?
C11B C10B H10B 120.2 . . ?
C9B C10B H10B 120.2 . . ?
C10B C11B C12B 120.03(12) . . ?
C10B C11B H11B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C11B C12B C7B 121.04(11) . . ?
C11B C12B H12B 119.5 . . ?
C7B C12B H12B 119.5 . . ?
C18B C13B C14B 121.42(10) . . ?
C18B C13B N2B 119.60(10) . . ?
C14B C13B N2B 118.98(10) . . ?
C15B C14B C13B 118.35(11) . . ?
C15B C14B C19B 121.04(11) . . ?
C13B C14B C19B 120.58(11) . . ?
C16B C15B C14B 121.14(12) . . ?
C16B C15B H15B 119.4 . . ?
C14B C15B H15B 119.4 . . ?
C15B C16B C17B 119.75(12) . . ?
C15B C16B H16B 120.1 . . ?
C17B C16B H16B 120.1 . . ?
C16B C17B C18B 121.27(12) . . ?
C16B C17B H17B 119.4 . . ?
C18B C17B H17B 119.4 . . ?
C17B C18B C13B 118.06(11) . . ?
C17B C18B C20B 121.02(11) . . ?
C13B C18B C20B 120.88(10) . . ?
C14B C19B H19A 109.5 . . ?
C14B C19B H19B 109.5 . . ?
H19A C19B H19B 109.5 . . ?
C14B C19B H19C 109.5 . . ?
H19A C19B H19C 109.5 . . ?
H19B C19B H19C 109.5 . . ?
C18B C20B H20A 109.5 . . ?
C18B C20B H20B 109.5 . . ?
H20A C20B H20B 109.5 . . ?
C18B C20B H20C 109.5 . . ?
H20A C20B H20C 109.5 . . ?
H20B C20B 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
C5A N1A C2A C3A -0.30(13) . . . . ?
C5A N1A C2A C6A -174.86(10) . . . . ?
N1A C2A C3A C4A -0.01(14) . . . . ?
C6A C2A C3A C4A 174.48(11) . . . . ?
C2A C3A C4A C5A 0.31(14) . . . . ?
C2A N1A C5A C4A 0.49(13) . . . . ?
C2A N1A C5A C7A 175.57(10) . . . . ?
C3A C4A C5A N1A -0.49(13) . . . . ?
C3A C4A C5A C7A -175.26(11) . . . . ?
C13A N2A C6A C2A 175.62(10) . . . . ?
N1A C2A C6A N2A 4.59(19) . . . . ?
C3A C2A C6A N2A -168.94(12) . . . . ?
N1A C5A C7A C12A -26.53(16) . . . . ?
C4A C5A C7A C12A 147.47(13) . . . . ?
N1A C5A C7A C8A 158.25(11) . . . . ?
C4A C5A C7A C8A -27.75(18) . . . . ?
C12A C7A C8A C9A -0.90(18) . . . . ?
C5A C7A C8A C9A 174.46(12) . . . . ?
C7A C8A C9A C10A 1.2(2) . . . . ?
C8A C9A C10A C11A -0.7(2) . . . . ?
C9A C10A C11A C12A -0.1(2) . . . . ?
C10A C11A C12A C7A 0.45(19) . . . . ?
C8A C7A C12A C11A 0.06(18) . . . . ?
C5A C7A C12A C11A -175.23(11) . . . . ?
C6A N2A C13A C14A 105.38(12) . . . . ?
C6A N2A C13A C18A -77.66(14) . . . . ?
C18A C13A C14A C15A -1.07(17) . . . . ?
N2A C13A C14A C15A 175.83(10) . . . . ?
C18A C13A C14A C19A 176.59(10) . . . . ?
N2A C13A C14A C19A -6.51(16) . . . . ?
C13A C14A C15A C16A -0.41(18) . . . . ?
C19A C14A C15A C16A -178.07(11) . . . . ?
C14A C15A C16A C17A 0.92(19) . . . . ?
C15A C16A C17A C18A 0.06(19) . . . . ?
C16A C17A C18A C13A -1.48(18) . . . . ?
C16A C17A C18A C20A 177.82(12) . . . . ?
C14A C13A C18A C17A 2.00(17) . . . . ?
N2A C13A C18A C17A -174.89(10) . . . . ?
C14A C13A C18A C20A -177.29(11) . . . . ?
N2A C13A C18A C20A 5.82(16) . . . . ?
C5B N1B C2B C3B -1.34(12) . . . . ?
C5B N1B C2B C6B 177.56(10) . . . . ?
N1B C2B C3B C4B 0.65(13) . . . . ?
C6B C2B C3B C4B -178.19(11) . . . . ?
C2B C3B C4B C5B 0.26(13) . . . . ?
C2B N1B C5B C4B 1.49(12) . . . . ?
C2B N1B C5B C7B 177.33(9) . . . . ?
C3B C4B C5B N1B -1.07(13) . . . . ?
C3B C4B C5B C7B -176.54(11) . . . . ?
C13B N2B C6B C2B -178.79(10) . . . . ?
N1B C2B C6B N2B 3.88(18) . . . . ?
C3B C2B C6B N2B -177.46(12) . . . . ?
N1B C5B C7B C12B -27.23(16) . . . . ?
C4B C5B C7B C12B 147.64(12) . . . . ?
N1B C5B C7B C8B 155.02(11) . . . . ?
C4B C5B C7B C8B -30.12(17) . . . . ?
C12B C7B C8B C9B 1.17(18) . . . . ?
C5B C7B C8B C9B 179.01(11) . . . . ?
C7B C8B C9B C10B -0.6(2) . . . . ?
C8B C9B C10B C11B -0.2(2) . . . . ?
C9B C10B C11B C12B 0.5(2) . . . . ?
C10B C11B C12B C7B 0.04(19) . . . . ?
C8B C7B C12B C11B -0.89(17) . . . . ?
C5B C7B C12B C11B -178.69(11) . . . . ?
C6B N2B C13B C18B -85.87(14) . . . . ?
C6B N2B C13B C14B 94.72(13) . . . . ?
C18B C13B C14B C15B 0.70(18) . . . . ?
N2B C13B C14B C15B -179.90(11) . . . . ?
C18B C13B C14B C19B 178.92(11) . . . . ?
N2B C13B C14B C19B -1.68(18) . . . . ?
C13B C14B C15B C16B 0.1(2) . . . . ?
C19B C14B C15B C16B -178.10(13) . . . . ?
C14B C15B C16B C17B -0.9(2) . . . . ?
C15B C16B C17B C18B 0.8(2) . . . . ?
C16B C17B C18B C13B -0.03(19) . . . . ?
C16B C17B C18B C20B 177.94(12) . . . . ?
C14B C13B C18B C17B -0.74(18) . . . . ?
N2B C13B C18B C17B 179.87(11) . . . . ?
C14B C13B C18B C20B -178.71(11) . . . . ?
N2B C13B C18B C20B 1.90(17) . . . . ?

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.050

_shelxl_version_number           2014-3

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_VII
_database_code_depnum_ccdc_archive 'CCDC 1853547'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C32 H44 N2'
_chemical_formula_sum            'C32 H44 N2'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         456.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.8624(9)
_cell_length_b                   12.9884(12)
_cell_length_c                   13.0264(11)
_cell_angle_alpha                70.021(5)
_cell_angle_beta                 74.259(5)
_cell_angle_gamma                68.722(4)
_cell_volume                     1440.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2667
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      25.53
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.053
_exptl_crystal_F_000             500
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.060
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12975
_diffrn_reflns_av_unetI/netI     0.0701
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.248
_diffrn_reflns_theta_max         25.920
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5428
_reflns_number_gt                3556
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2014
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5428
_refine_ls_number_parameters     321
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.1085
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
N1 N 0.52508(15) 0.31675(11) 0.32929(11) 0.0241(3) Uani 1 1 d . . . . .
N2 N 0.35747(14) 0.46612(11) 0.46833(10) 0.0253(3) Uani 1 1 d . . . . .
C2 C 0.37409(17) 0.35257(14) 0.35357(13) 0.0259(4) Uani 1 1 d . . . . .
C3 C 0.32271(19) 0.30616(15) 0.29682(14) 0.0350(4) Uani 1 1 d . . . . .
H3 H 0.222206 0.315994 0.297588 0.042 Uiso 1 1 calc R U . . .
C4 C 0.44587(19) 0.24180(16) 0.23774(15) 0.0362(5) Uani 1 1 d . . . . .
H4 H 0.443507 0.200495 0.190835 0.043 Uiso 1 1 calc R U . . .
C5 C 0.57053(18) 0.24869(14) 0.25930(13) 0.0273(4) Uani 1 1 d . . . . .
C6 C 0.29422(18) 0.42619(14) 0.42439(12) 0.0255(4) Uani 1 1 d . . . . .
H6 H 0.189528 0.446078 0.439212 0.031 Uiso 1 1 calc R U . . .
C7 C 0.72906(18) 0.19471(14) 0.22017(13) 0.0264(4) Uani 1 1 d . . . . .
C8 C 0.80242(18) 0.25255(14) 0.12168(13) 0.0285(4) Uani 1 1 d . . . . .
C9 C 0.94948(19) 0.19805(16) 0.08544(14) 0.0327(4) Uani 1 1 d . . . . .
H9 H 0.999656 0.236032 0.018179 0.039 Uiso 1 1 calc R U . . .
C10 C 1.02512(18) 0.09034(15) 0.14414(14) 0.0324(4) Uani 1 1 d . . . . .
C11 C 0.95017(19) 0.03616(15) 0.24148(15) 0.0332(4) Uani 1 1 d . . . . .
H11 H 1.000973 -0.037625 0.282581 0.040 Uiso 1 1 calc R U . . .
C12 C 0.80310(18) 0.08578(14) 0.28139(14) 0.0284(4) Uani 1 1 d . . . . .
C13 C 0.7226(2) 0.37012(16) 0.05445(14) 0.0376(5) Uani 1 1 d . . . . .
H13 H 0.632952 0.403964 0.104415 0.045 Uiso 1 1 calc R U . . .
C14 C 0.6709(2) 0.3585(2) -0.03996(17) 0.0598(6) Uani 1 1 d . . . . .
H14A H 0.756267 0.320707 -0.087661 0.090 Uiso 1 1 calc R U . . .
H14B H 0.621015 0.434868 -0.083492 0.090 Uiso 1 1 calc R U . . .
H14C H 0.602210 0.312461 -0.009486 0.090 Uiso 1 1 calc R U . . .
C15 C 0.8148(3) 0.45300(17) 0.00918(17) 0.0549(6) Uani 1 1 d . . . . .
H15A H 0.853564 0.455704 0.069690 0.082 Uiso 1 1 calc R U . . .
H15B H 0.753130 0.529801 -0.024094 0.082 Uiso 1 1 calc R U . . .
H15C H 0.897142 0.426816 -0.047170 0.082 Uiso 1 1 calc R U . . .
C16 C 0.72421(19) 0.02135(15) 0.38718(14) 0.0345(4) Uani 1 1 d . . . . .
H16 H 0.643692 0.079949 0.420637 0.041 Uiso 1 1 calc R U . . .
C17 C 0.6514(2) -0.05133(18) 0.36226(18) 0.0537(6) Uani 1 1 d . . . . .
H17A H 0.578936 -0.001360 0.313687 0.081 Uiso 1 1 calc R U . . .
H17B H 0.601670 -0.092183 0.431705 0.081 Uiso 1 1 calc R U . . .
H17C H 0.726925 -0.107026 0.325439 0.081 Uiso 1 1 calc R U . . .
C18 C 0.8222(2) -0.05445(16) 0.47408(15) 0.0472(5) Uani 1 1 d . . . . .
H18A H 0.893980 -0.119428 0.448022 0.071 Uiso 1 1 calc R U . . .
H18B H 0.761007 -0.083118 0.543681 0.071 Uiso 1 1 calc R U . . .
H18C H 0.874556 -0.009515 0.486365 0.071 Uiso 1 1 calc R U . . .
C19 C 1.18605(19) 0.03284(17) 0.10394(16) 0.0414(5) Uani 1 1 d . . . . .
H19 H 1.215497 -0.043525 0.158974 0.050 Uiso 1 1 calc R U . . .
C20 C 1.2100(2) 0.00961(19) -0.00704(18) 0.0562(6) Uani 1 1 d . . . . .
H20A H 1.181159 0.082498 -0.063490 0.084 Uiso 1 1 calc R U . . .
H20B H 1.149965 -0.038398 -0.001640 0.084 Uiso 1 1 calc R U . . .
H20C H 1.314537 -0.030302 -0.027744 0.084 Uiso 1 1 calc R U . . .
C21 C 1.2844(2) 0.0993(2) 0.10334(18) 0.0568(6) Uani 1 1 d . . . . .
H21A H 1.258028 0.175565 0.051111 0.085 Uiso 1 1 calc R U . . .
H21B H 1.387684 0.058091 0.080672 0.085 Uiso 1 1 calc R U . . .
H21C H 1.271226 0.107296 0.177843 0.085 Uiso 1 1 calc R U . . .
C22 C 0.26614(17) 0.54061(14) 0.53546(13) 0.0237(4) Uani 1 1 d . . . . .
C23 C 0.26325(17) 0.65672(14) 0.49567(13) 0.0249(4) Uani 1 1 d . . . . .
C24 C 0.17417(18) 0.73024(15) 0.55974(14) 0.0290(4) Uani 1 1 d . . . . .
H24 H 0.169230 0.809124 0.533425 0.035 Uiso 1 1 calc R U . . .
C25 C 0.09229(18) 0.69149(16) 0.66109(14) 0.0325(4) Uani 1 1 d . . . . .
H25 H 0.030396 0.743461 0.703261 0.039 Uiso 1 1 calc R U . . .
C26 C 0.10131(18) 0.57737(16) 0.70011(14) 0.0324(4) Uani 1 1 d . . . . .
H26 H 0.046133 0.550940 0.770382 0.039 Uiso 1 1 calc R U . . .
C27 C 0.18933(18) 0.49856(15) 0.63958(13) 0.0280(4) Uani 1 1 d . . . . .
C28 C 0.2031(2) 0.37184(15) 0.69034(14) 0.0360(4) Uani 1 1 d . . . . .
H28 H 0.279842 0.329109 0.639145 0.043 Uiso 1 1 calc R U . . .
C29 C 0.0595(2) 0.34700(17) 0.70109(17) 0.0482(5) Uani 1 1 d . . . . .
H29A H -0.020272 0.393225 0.745433 0.072 Uiso 1 1 calc R U . . .
H29B H 0.071031 0.265359 0.737502 0.072 Uiso 1 1 calc R U . . .
H29C H 0.035315 0.366456 0.627248 0.072 Uiso 1 1 calc R U . . .
C30 C 0.2560(2) 0.32771(17) 0.80202(15) 0.0498(5) Uani 1 1 d . . . . .
H30A H 0.344195 0.349873 0.793854 0.075 Uiso 1 1 calc R U . . .
H30B H 0.279982 0.243872 0.827030 0.075 Uiso 1 1 calc R U . . .
H30C H 0.177879 0.361140 0.856690 0.075 Uiso 1 1 calc R U . . .
C31 C 0.35549(18) 0.69691(15) 0.38460(13) 0.0282(4) Uani 1 1 d . . . . .
H31 H 0.451448 0.634829 0.378974 0.034 Uiso 1 1 calc R U . . .
C32 C 0.2812(2) 0.71384(16) 0.28901(14) 0.0387(5) Uani 1 1 d . . . . .
H32A H 0.185219 0.772813 0.293414 0.058 Uiso 1 1 calc R U . . .
H32B H 0.266935 0.641404 0.293760 0.058 Uiso 1 1 calc R U . . .
H32C H 0.343721 0.738183 0.218453 0.058 Uiso 1 1 calc R U . . .
C33 C 0.3907(2) 0.80631(16) 0.37162(15) 0.0384(5) Uani 1 1 d . . . . .
H33A H 0.299241 0.870321 0.371234 0.058 Uiso 1 1 calc R U . . .
H33B H 0.458111 0.823347 0.301722 0.058 Uiso 1 1 calc R U . . .
H33C H 0.437432 0.795504 0.433566 0.058 Uiso 1 1 calc R U . . .
H1 H 0.5823(18) 0.3352(14) 0.3567(13) 0.027(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.3620(19) . ?
N1 C2 1.370(2) . ?
N1 H1 0.877(16) . ?
N2 C6 1.2716(19) . ?
N2 C22 1.4249(19) . ?
C2 C3 1.377(2) . ?
C2 C6 1.431(2) . ?
C3 C4 1.401(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.372(2) . ?
C4 H4 0.9500 . ?
C5 C7 1.487(2) . ?
C6 H6 0.9500 . ?
C7 C12 1.402(2) . ?
C7 C8 1.402(2) . ?
C8 C9 1.393(2) . ?
C8 C13 1.519(2) . ?
C9 C10 1.385(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(2) . ?
C10 C19 1.519(2) . ?
C11 C12 1.390(2) . ?
C11 H11 0.9500 . ?
C12 C16 1.519(2) . ?
C13 C14 1.522(2) . ?
C13 C15 1.523(3) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C18 1.525(3) . ?
C16 C17 1.530(2) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C21 1.511(3) . ?
C19 C20 1.516(3) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C27 1.396(2) . ?
C22 C23 1.409(2) . ?
C23 C24 1.385(2) . ?
C23 C31 1.519(2) . ?
C24 C25 1.382(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.370(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.399(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.519(2) . ?
C28 C29 1.524(3) . ?
C28 C30 1.531(3) . ?
C28 H28 1.0000 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.525(2) . ?
C31 C33 1.527(2) . ?
C31 H31 1.0000 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 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
C5 N1 C2 110.31(13) . . ?
C5 N1 H1 126.2(10) . . ?
C2 N1 H1 123.5(10) . . ?
C6 N2 C22 117.69(13) . . ?
N1 C2 C3 107.05(14) . . ?
N1 C2 C6 123.08(14) . . ?
C3 C2 C6 129.87(15) . . ?
C2 C3 C4 107.41(15) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
C5 C4 C3 108.22(15) . . ?
C5 C4 H4 125.9 . . ?
C3 C4 H4 125.9 . . ?
N1 C5 C4 107.00(15) . . ?
N1 C5 C7 122.67(14) . . ?
C4 C5 C7 130.32(14) . . ?
N2 C6 C2 122.77(15) . . ?
N2 C6 H6 118.6 . . ?
C2 C6 H6 118.6 . . ?
C12 C7 C8 120.67(15) . . ?
C12 C7 C5 119.64(16) . . ?
C8 C7 C5 119.68(15) . . ?
C9 C8 C7 118.26(16) . . ?
C9 C8 C13 120.76(16) . . ?
C7 C8 C13 120.96(15) . . ?
C10 C9 C8 122.25(17) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C11 C10 C9 118.07(16) . . ?
C11 C10 C19 120.45(16) . . ?
C9 C10 C19 121.48(17) . . ?
C10 C11 C12 122.32(17) . . ?
C10 C11 H11 118.8 . . ?
C12 C11 H11 118.8 . . ?
C11 C12 C7 118.43(16) . . ?
C11 C12 C16 120.36(16) . . ?
C7 C12 C16 121.19(15) . . ?
C8 C13 C14 110.13(15) . . ?
C8 C13 C15 113.47(16) . . ?
C14 C13 C15 110.02(16) . . ?
C8 C13 H13 107.7 . . ?
C14 C13 H13 107.7 . . ?
C15 C13 H13 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 C18 114.25(15) . . ?
C12 C16 C17 111.04(15) . . ?
C18 C16 C17 109.22(16) . . ?
C12 C16 H16 107.3 . . ?
C18 C16 H16 107.3 . . ?
C17 C16 H16 107.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C19 C20 111.99(17) . . ?
C21 C19 C10 111.45(16) . . ?
C20 C19 C10 112.66(15) . . ?
C21 C19 H19 106.8 . . ?
C20 C19 H19 106.8 . . ?
C10 C19 H19 106.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 121.31(14) . . ?
C27 C22 N2 121.08(14) . . ?
C23 C22 N2 117.51(14) . . ?
C24 C23 C22 118.12(15) . . ?
C24 C23 C31 122.55(15) . . ?
C22 C23 C31 119.33(13) . . ?
C25 C24 C23 121.53(16) . . ?
C25 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C26 C25 C24 119.33(15) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C25 C26 C27 121.99(16) . . ?
C25 C26 H26 119.0 . . ?
C27 C26 H26 119.0 . . ?
C22 C27 C26 117.58(16) . . ?
C22 C27 C28 122.73(14) . . ?
C26 C27 C28 119.63(15) . . ?
C27 C28 C29 111.84(15) . . ?
C27 C28 C30 111.06(15) . . ?
C29 C28 C30 111.23(16) . . ?
C27 C28 H28 107.5 . . ?
C29 C28 H28 107.5 . . ?
C30 C28 H28 107.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C23 C31 C32 111.07(13) . . ?
C23 C31 C33 113.55(13) . . ?
C32 C31 C33 109.64(14) . . ?
C23 C31 H31 107.4 . . ?
C32 C31 H31 107.4 . . ?
C33 C31 H31 107.4 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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
C5 N1 C2 C3 -0.28(19) . . . . ?
C5 N1 C2 C6 -179.37(15) . . . . ?
N1 C2 C3 C4 -0.1(2) . . . . ?
C6 C2 C3 C4 178.93(17) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C2 N1 C5 C4 0.5(2) . . . . ?
C2 N1 C5 C7 -178.60(15) . . . . ?
C3 C4 C5 N1 -0.6(2) . . . . ?
C3 C4 C5 C7 178.47(18) . . . . ?
C22 N2 C6 C2 178.67(15) . . . . ?
N1 C2 C6 N2 1.6(3) . . . . ?
C3 C2 C6 N2 -177.26(17) . . . . ?
N1 C5 C7 C12 89.7(2) . . . . ?
C4 C5 C7 C12 -89.2(2) . . . . ?
N1 C5 C7 C8 -91.16(19) . . . . ?
C4 C5 C7 C8 89.9(2) . . . . ?
C12 C7 C8 C9 1.2(2) . . . . ?
C5 C7 C8 C9 -177.94(13) . . . . ?
C12 C7 C8 C13 179.49(14) . . . . ?
C5 C7 C8 C13 0.4(2) . . . . ?
C7 C8 C9 C10 -1.0(2) . . . . ?
C13 C8 C9 C10 -179.32(16) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C8 C9 C10 C19 -179.31(15) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C19 C10 C11 C12 179.84(15) . . . . ?
C10 C11 C12 C7 0.0(2) . . . . ?
C10 C11 C12 C16 178.26(15) . . . . ?
C8 C7 C12 C11 -0.7(2) . . . . ?
C5 C7 C12 C11 178.43(14) . . . . ?
C8 C7 C12 C16 -178.96(14) . . . . ?
C5 C7 C12 C16 0.2(2) . . . . ?
C9 C8 C13 C14 80.7(2) . . . . ?
C7 C8 C13 C14 -97.54(18) . . . . ?
C9 C8 C13 C15 -43.1(2) . . . . ?
C7 C8 C13 C15 138.64(17) . . . . ?
C11 C12 C16 C18 34.2(2) . . . . ?
C7 C12 C16 C18 -147.53(16) . . . . ?
C11 C12 C16 C17 -89.83(19) . . . . ?
C7 C12 C16 C17 88.41(19) . . . . ?
C11 C10 C19 C21 -115.3(2) . . . . ?
C9 C10 C19 C21 64.3(2) . . . . ?
C11 C10 C19 C20 117.85(19) . . . . ?
C9 C10 C19 C20 -62.5(2) . . . . ?
C6 N2 C22 C27 71.6(2) . . . . ?
C6 N2 C22 C23 -112.12(17) . . . . ?
C27 C22 C23 C24 -4.1(2) . . . . ?
N2 C22 C23 C24 179.58(14) . . . . ?
C27 C22 C23 C31 176.59(14) . . . . ?
N2 C22 C23 C31 0.3(2) . . . . ?
C22 C23 C24 C25 1.4(2) . . . . ?
C31 C23 C24 C25 -179.35(15) . . . . ?
C23 C24 C25 C26 1.2(2) . . . . ?
C24 C25 C26 C27 -1.1(2) . . . . ?
C23 C22 C27 C26 4.2(2) . . . . ?
N2 C22 C27 C26 -179.64(14) . . . . ?
C23 C22 C27 C28 -173.20(14) . . . . ?
N2 C22 C27 C28 3.0(2) . . . . ?
C25 C26 C27 C22 -1.6(2) . . . . ?
C25 C26 C27 C28 175.90(15) . . . . ?
C22 C27 C28 C29 -113.22(18) . . . . ?
C26 C27 C28 C29 69.5(2) . . . . ?
C22 C27 C28 C30 121.87(17) . . . . ?
C26 C27 C28 C30 -55.4(2) . . . . ?
C24 C23 C31 C32 -100.88(17) . . . . ?
C22 C23 C31 C32 78.39(18) . . . . ?
C24 C23 C31 C33 23.2(2) . . . . ?
C22 C23 C31 C33 -157.50(14) . . . . ?

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.041

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?


####################################################################### 
# 
# 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_III
_database_code_depnum_ccdc_archive 'CCDC 1853545'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H9 F5 N2'
_chemical_formula_sum            'C17 H9 F5 N2'
_chemical_melting_point          ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         336.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   4.79220(10)
_cell_length_b                   13.7718(3)
_cell_length_c                   20.8410(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1375.45(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5144
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      31.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.145
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26413
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.284
_diffrn_reflns_theta_max         37.805
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7277
_reflns_number_gt                5370
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_max     0.973
_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0634P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1840 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   'P 21 21 21'
_symmetry_int_tables_number      19
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7277
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_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
F1 F 1.1485(3) 0.77393(7) 0.81820(5) 0.0260(2) Uani 1 1 d . . . . .
F2 F 1.5237(2) 0.78648(8) 0.91327(5) 0.0292(2) Uani 1 1 d . . . . .
F3 F 1.5427(3) 0.64806(9) 1.00677(5) 0.0317(3) Uani 1 1 d . . . . .
F4 F 1.1731(3) 0.49921(8) 1.00421(5) 0.0343(3) Uani 1 1 d . . . . .
F5 F 0.7946(2) 0.48503(8) 0.91037(5) 0.0281(2) Uani 1 1 d . . . . .
N1 N 0.3378(3) 0.61994(10) 0.71482(6) 0.0171(2) Uani 1 1 d . . . . .
N2 N 0.7627(3) 0.62735(10) 0.81004(6) 0.0183(2) Uani 1 1 d . . . . .
C2 C 0.4834(3) 0.54007(12) 0.73557(7) 0.0180(3) Uani 1 1 d . . . . .
C3 C 0.3800(4) 0.46066(12) 0.70283(8) 0.0217(3) Uani 1 1 d . . . . .
H3 H 0.4414 0.3954 0.7073 0.026 Uiso 1 1 calc R U . . .
C4 C 0.1688(4) 0.49336(12) 0.66190(8) 0.0208(3) Uani 1 1 d . . . . .
H4 H 0.0602 0.4543 0.6338 0.025 Uiso 1 1 calc R U . . .
C5 C 0.1465(3) 0.59348(11) 0.66965(7) 0.0166(3) Uani 1 1 d . . . . .
C6 C 0.6990(3) 0.54611(12) 0.78260(7) 0.0188(3) Uani 1 1 d . . . . .
H6 H 0.7984 0.4890 0.7940 0.023 Uiso 1 1 calc R U . . .
C7 C -0.0457(3) 0.66209(11) 0.63966(7) 0.0165(3) Uani 1 1 d . . . . .
C8 C -0.1989(4) 0.63439(12) 0.58573(8) 0.0205(3) Uani 1 1 d . . . . .
H8 H -0.1734 0.5714 0.5681 0.025 Uiso 1 1 calc R U . . .
C9 C -0.3873(4) 0.69750(13) 0.55750(8) 0.0237(3) Uani 1 1 d . . . . .
H9 H -0.4910 0.6774 0.5210 0.028 Uiso 1 1 calc R U . . .
C10 C -0.4253(4) 0.79037(13) 0.58249(8) 0.0239(3) Uani 1 1 d . . . . .
H10 H -0.5533 0.8340 0.5630 0.029 Uiso 1 1 calc R U . . .
C11 C -0.2745(4) 0.81852(12) 0.63614(8) 0.0246(3) Uani 1 1 d . . . . .
H11 H -0.3003 0.8817 0.6535 0.029 Uiso 1 1 calc R U . . .
C12 C -0.0865(4) 0.75539(11) 0.66463(8) 0.0207(3) Uani 1 1 d . . . . .
H12 H 0.0155 0.7756 0.7014 0.025 Uiso 1 1 calc R U . . .
C13 C 0.9648(3) 0.62699(11) 0.85858(7) 0.0171(3) Uani 1 1 d . . . . .
C14 C 1.1519(4) 0.70417(11) 0.86310(7) 0.0180(3) Uani 1 1 d . . . . .
C15 C 1.3450(4) 0.71174(12) 0.91184(8) 0.0200(3) Uani 1 1 d . . . . .
C16 C 1.3548(4) 0.64203(12) 0.95928(8) 0.0216(3) Uani 1 1 d . . . . .
C17 C 1.1703(4) 0.56588(12) 0.95755(8) 0.0212(3) Uani 1 1 d . . . . .
C18 C 0.9792(4) 0.55852(11) 0.90807(8) 0.0191(3) Uani 1 1 d . . . . .
H1 H 0.376(6) 0.6736(18) 0.7271(12) 0.040(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C14 1.3412(18) . ?
F2 C15 1.3394(19) . ?
F3 C16 1.3407(19) . ?
F4 C17 1.3375(19) . ?
F5 C18 1.3452(19) . ?
N1 C5 1.364(2) . ?
N1 C2 1.372(2) . ?
N1 H1 0.80(3) . ?
N2 C6 1.293(2) . ?
N2 C13 1.400(2) . ?
C2 C3 1.381(2) . ?
C2 C6 1.427(2) . ?
C3 C4 1.398(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(2) . ?
C4 H4 0.9500 . ?
C5 C7 1.460(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(2) . ?
C7 C12 1.400(2) . ?
C8 C9 1.385(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.393(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.394(2) . ?
C13 C18 1.399(2) . ?
C14 C15 1.378(2) . ?
C15 C16 1.379(2) . ?
C16 C17 1.372(2) . ?
C17 C18 1.383(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C2 110.20(13) . . ?
C5 N1 H1 128.2(19) . . ?
C2 N1 H1 121(2) . . ?
C6 N2 C13 118.66(14) . . ?
N1 C2 C3 107.24(13) . . ?
N1 C2 C6 122.55(14) . . ?
C3 C2 C6 130.22(15) . . ?
C2 C3 C4 107.84(14) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
C5 C4 C3 107.69(14) . . ?
C5 C4 H4 126.2 . . ?
C3 C4 H4 126.2 . . ?
N1 C5 C4 107.03(14) . . ?
N1 C5 C7 123.14(14) . . ?
C4 C5 C7 129.78(15) . . ?
N2 C6 C2 121.68(15) . . ?
N2 C6 H6 119.2 . . ?
C2 C6 H6 119.2 . . ?
C8 C7 C12 118.47(15) . . ?
C8 C7 C5 119.97(14) . . ?
C12 C7 C5 121.54(14) . . ?
C9 C8 C7 120.91(15) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 120.18(16) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 119.35(16) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 120.59(16) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 120.50(15) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C14 C13 C18 115.62(14) . . ?
C14 C13 N2 119.41(14) . . ?
C18 C13 N2 124.68(14) . . ?
F1 C14 C15 117.91(14) . . ?
F1 C14 C13 119.44(14) . . ?
C15 C14 C13 122.65(14) . . ?
F2 C15 C14 120.26(14) . . ?
F2 C15 C16 119.84(15) . . ?
C14 C15 C16 119.90(15) . . ?
F3 C16 C17 119.98(15) . . ?
F3 C16 C15 120.59(16) . . ?
C17 C16 C15 119.44(15) . . ?
F4 C17 C16 119.94(15) . . ?
F4 C17 C18 119.90(15) . . ?
C16 C17 C18 120.16(15) . . ?
F5 C18 C17 117.66(14) . . ?
F5 C18 C13 120.05(14) . . ?
C17 C18 C13 122.21(15) . . ?

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
C5 N1 C2 C3 -0.35(18) . . . . ?
C5 N1 C2 C6 179.54(15) . . . . ?
N1 C2 C3 C4 -0.10(19) . . . . ?
C6 C2 C3 C4 -179.99(17) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C2 N1 C5 C4 0.66(18) . . . . ?
C2 N1 C5 C7 178.31(14) . . . . ?
C3 C4 C5 N1 -0.71(19) . . . . ?
C3 C4 C5 C7 -178.14(16) . . . . ?
C13 N2 C6 C2 176.16(15) . . . . ?
N1 C2 C6 N2 2.5(2) . . . . ?
C3 C2 C6 N2 -177.65(18) . . . . ?
N1 C5 C7 C8 168.00(15) . . . . ?
C4 C5 C7 C8 -14.9(3) . . . . ?
N1 C5 C7 C12 -13.6(2) . . . . ?
C4 C5 C7 C12 163.52(18) . . . . ?
C12 C7 C8 C9 -0.1(2) . . . . ?
C5 C7 C8 C9 178.39(16) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C7 0.0(3) . . . . ?
C8 C7 C12 C11 -0.1(2) . . . . ?
C5 C7 C12 C11 -178.60(16) . . . . ?
C6 N2 C13 C14 142.44(16) . . . . ?
C6 N2 C13 C18 -44.1(2) . . . . ?
C18 C13 C14 F1 -178.85(14) . . . . ?
N2 C13 C14 F1 -4.8(2) . . . . ?
C18 C13 C14 C15 1.9(2) . . . . ?
N2 C13 C14 C15 175.94(15) . . . . ?
F1 C14 C15 F2 -0.6(2) . . . . ?
C13 C14 C15 F2 178.71(15) . . . . ?
F1 C14 C15 C16 179.57(15) . . . . ?
C13 C14 C15 C16 -1.2(2) . . . . ?
F2 C15 C16 F3 -0.3(2) . . . . ?
C14 C15 C16 F3 179.55(15) . . . . ?
F2 C15 C16 C17 179.80(16) . . . . ?
C14 C15 C16 C17 -0.3(2) . . . . ?
F3 C16 C17 F4 1.9(3) . . . . ?
C15 C16 C17 F4 -178.27(15) . . . . ?
F3 C16 C17 C18 -178.92(15) . . . . ?
C15 C16 C17 C18 1.0(3) . . . . ?
F4 C17 C18 F5 2.3(2) . . . . ?
C16 C17 C18 F5 -176.88(15) . . . . ?
F4 C17 C18 C13 179.09(16) . . . . ?
C16 C17 C18 C13 -0.1(3) . . . . ?
C14 C13 C18 F5 175.42(14) . . . . ?
N2 C13 C18 F5 1.7(2) . . . . ?
C14 C13 C18 C17 -1.2(2) . . . . ?
N2 C13 C18 C17 -174.92(16) . . . . ?

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.061

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_IV
_database_code_depnum_ccdc_archive 'CCDC 1853546'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C21 H22 N2'
_chemical_formula_sum            'C21 H22 N2'
_chemical_melting_point          ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         302.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   11.818(2)
_cell_length_b                   11.243(2)
_cell_length_c                   26.174(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.984(10)
_cell_angle_gamma                90
_cell_volume                     3473.2(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1693
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      22.74
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11759
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.117
_diffrn_reflns_theta_max         25.694
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3269
_reflns_number_gt                2201
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0616P)²+0.4812P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3269
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1308
_refine_ls_wR_factor_gt          0.1206
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
N1 N 0.16527(14) 0.09527(14) 0.23280(6) 0.0211(4) Uani 1 1 d . . . . .
N2 N 0.04754(13) 0.17557(14) 0.32062(6) 0.0227(4) Uani 1 1 d . . . . .
C2 C 0.21454(16) 0.15808(17) 0.27353(7) 0.0218(4) Uani 1 1 d . . . . .
C3 C 0.32916(16) 0.16520(18) 0.26614(7) 0.0263(5) Uani 1 1 d . . . . .
H3 H 0.3845 0.2028 0.2883 0.032 Uiso 1 1 calc R U . . .
C4 C 0.34928(16) 0.10718(18) 0.22023(7) 0.0258(5) Uani 1 1 d . . . . .
H4 H 0.4207 0.0985 0.2056 0.031 Uiso 1 1 calc R U . . .
C5 C 0.24684(15) 0.06475(16) 0.19984(7) 0.0209(4) Uani 1 1 d . . . . .
C6 C 0.15290(16) 0.19787(16) 0.31591(7) 0.0225(5) Uani 1 1 d . . . . .
H6 H 0.1920 0.2431 0.3419 0.027 Uiso 1 1 calc R U . . .
C7 C 0.22243(15) -0.00439(16) 0.15329(7) 0.0206(4) Uani 1 1 d . . . . .
C8 C 0.29547(16) 0.00194(17) 0.11344(7) 0.0239(5) Uani 1 1 d . . . . .
H8 H 0.3584 0.0545 0.1163 0.029 Uiso 1 1 calc R U . . .
C9 C 0.27894(16) -0.06624(17) 0.06966(7) 0.0243(5) Uani 1 1 d . . . . .
C10 C 0.18709(17) -0.14382(17) 0.06636(8) 0.0267(5) Uani 1 1 d . . . . .
H10 H 0.1752 -0.1919 0.0367 0.032 Uiso 1 1 calc R U . . .
C11 C 0.11219(17) -0.15249(17) 0.10552(7) 0.0248(5) Uani 1 1 d . . . . .
C12 C 0.12986(16) -0.08194(17) 0.14836(7) 0.0225(4) Uani 1 1 d . . . . .
H12 H 0.0783 -0.0861 0.1750 0.027 Uiso 1 1 calc R U . . .
C13 C 0.35967(18) -0.0567(2) 0.02711(8) 0.0345(5) Uani 1 1 d . . . . .
H13A H 0.4278 -0.1037 0.0358 0.052 Uiso 1 1 calc R U . . .
H13B H 0.3808 0.0268 0.0226 0.052 Uiso 1 1 calc R U . . .
H13C H 0.3229 -0.0869 -0.0047 0.052 Uiso 1 1 calc R U . . .
C14 C 0.01679(18) -0.24222(19) 0.10194(8) 0.0350(5) Uani 1 1 d . . . . .
H14A H 0.0478 -0.3224 0.1072 0.053 Uiso 1 1 calc R U . . .
H14B H -0.0222 -0.2374 0.0680 0.053 Uiso 1 1 calc R U . . .
H14C H -0.0370 -0.2250 0.1282 0.053 Uiso 1 1 calc R U . . .
C15 C -0.00269(16) 0.20817(17) 0.36735(7) 0.0226(5) Uani 1 1 d . . . . .
C16 C -0.08603(17) 0.29569(17) 0.36663(8) 0.0282(5) Uani 1 1 d . . . . .
C17 C -0.14308(17) 0.3145(2) 0.41129(9) 0.0363(6) Uani 1 1 d . . . . .
H17 H -0.1999 0.3742 0.4117 0.044 Uiso 1 1 calc R U . . .
C18 C -0.11876(18) 0.2486(2) 0.45465(8) 0.0370(6) Uani 1 1 d . . . . .
H18 H -0.1598 0.2617 0.4844 0.044 Uiso 1 1 calc R U . . .
C19 C -0.03486(18) 0.1636(2) 0.45497(8) 0.0316(5) Uani 1 1 d . . . . .
H19 H -0.0180 0.1189 0.4852 0.038 Uiso 1 1 calc R U . . .
C20 C 0.02553(17) 0.14218(17) 0.41183(7) 0.0252(5) Uani 1 1 d . . . . .
C21 C -0.1127(2) 0.3695(2) 0.31962(9) 0.0428(6) Uani 1 1 d . . . . .
H21A H -0.0420 0.3915 0.3040 0.064 Uiso 1 1 calc R U . . .
H21B H -0.1530 0.4417 0.3291 0.064 Uiso 1 1 calc R U . . .
H21C H -0.1604 0.3235 0.2951 0.064 Uiso 1 1 calc R U . . .
C22 C 0.11753(17) 0.04969(19) 0.41321(8) 0.0318(5) Uani 1 1 d . . . . .
H22A H 0.1916 0.0889 0.4137 0.048 Uiso 1 1 calc R U . . .
H22B H 0.1084 -0.0010 0.3828 0.048 Uiso 1 1 calc R U . . .
H22C H 0.1126 0.0008 0.4440 0.048 Uiso 1 1 calc R U . . .
H1 H 0.088(2) 0.098(2) 0.2234(9) 0.051(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.370(2) . ?
N1 C2 1.382(2) . ?
N1 H1 0.93(2) . ?
N2 C6 1.282(2) . ?
N2 C15 1.435(2) . ?
C2 C3 1.380(3) . ?
C2 C6 1.430(3) . ?
C3 C4 1.399(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C7 1.461(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(2) . ?
C7 C12 1.400(3) . ?
C8 C9 1.384(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(3) . ?
C9 C13 1.508(3) . ?
C10 C11 1.392(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(3) . ?
C11 C14 1.512(3) . ?
C12 H12 0.9500 . ?
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 C16 1.392(3) . ?
C15 C20 1.406(3) . ?
C16 C17 1.396(3) . ?
C16 C21 1.504(3) . ?
C17 C18 1.373(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.377(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(3) . ?
C19 H19 0.9500 . ?
C20 C22 1.504(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C5 N1 C2 109.37(16) . . ?
C5 N1 H1 123.4(14) . . ?
C2 N1 H1 123.8(14) . . ?
C6 N2 C15 118.61(16) . . ?
C3 C2 N1 107.38(17) . . ?
C3 C2 C6 129.32(18) . . ?
N1 C2 C6 123.17(17) . . ?
C2 C3 C4 107.77(18) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
C5 C4 C3 107.94(17) . . ?
C5 C4 H4 126.0 . . ?
C3 C4 H4 126.0 . . ?
N1 C5 C4 107.53(16) . . ?
N1 C5 C7 122.91(17) . . ?
C4 C5 C7 129.53(17) . . ?
N2 C6 C2 123.34(18) . . ?
N2 C6 H6 118.3 . . ?
C2 C6 H6 118.3 . . ?
C8 C7 C12 118.40(17) . . ?
C8 C7 C5 119.68(17) . . ?
C12 C7 C5 121.85(16) . . ?
C9 C8 C7 121.77(18) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 118.33(17) . . ?
C8 C9 C13 120.30(18) . . ?
C10 C9 C13 121.37(18) . . ?
C9 C10 C11 121.46(18) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 118.86(18) . . ?
C12 C11 C14 120.97(17) . . ?
C10 C11 C14 120.10(18) . . ?
C11 C12 C7 121.15(17) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 121.44(17) . . ?
C16 C15 N2 119.54(18) . . ?
C20 C15 N2 118.71(17) . . ?
C15 C16 C17 117.94(19) . . ?
C15 C16 C21 121.29(18) . . ?
C17 C16 C21 120.77(19) . . ?
C18 C17 C16 121.4(2) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 119.95(19) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 121.1(2) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C15 118.18(19) . . ?
C19 C20 C22 120.15(18) . . ?
C15 C20 C22 121.67(17) . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
C5 N1 C2 C3 -0.9(2) . . . . ?
C5 N1 C2 C6 -176.93(17) . . . . ?
N1 C2 C3 C4 0.6(2) . . . . ?
C6 C2 C3 C4 176.30(19) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C2 N1 C5 C4 0.8(2) . . . . ?
C2 N1 C5 C7 178.79(16) . . . . ?
C3 C4 C5 N1 -0.5(2) . . . . ?
C3 C4 C5 C7 -178.23(19) . . . . ?
C15 N2 C6 C2 173.05(17) . . . . ?
C3 C2 C6 N2 -172.8(2) . . . . ?
N1 C2 C6 N2 2.3(3) . . . . ?
N1 C5 C7 C8 157.80(18) . . . . ?
C4 C5 C7 C8 -24.7(3) . . . . ?
N1 C5 C7 C12 -25.3(3) . . . . ?
C4 C5 C7 C12 152.2(2) . . . . ?
C12 C7 C8 C9 -0.2(3) . . . . ?
C5 C7 C8 C9 176.79(17) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C7 C8 C9 C13 179.75(18) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C13 C9 C10 C11 -179.75(18) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C9 C10 C11 C14 -176.83(18) . . . . ?
C10 C11 C12 C7 -1.3(3) . . . . ?
C14 C11 C12 C7 175.75(18) . . . . ?
C8 C7 C12 C11 1.3(3) . . . . ?
C5 C7 C12 C11 -175.66(18) . . . . ?
C6 N2 C15 C16 114.3(2) . . . . ?
C6 N2 C15 C20 -72.1(2) . . . . ?
C20 C15 C16 C17 -1.4(3) . . . . ?
N2 C15 C16 C17 172.02(18) . . . . ?
C20 C15 C16 C21 177.47(19) . . . . ?
N2 C15 C16 C21 -9.1(3) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C21 C16 C17 C18 -179.3(2) . . . . ?
C16 C17 C18 C19 1.4(3) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C18 C19 C20 C15 -1.2(3) . . . . ?
C18 C19 C20 C22 179.42(19) . . . . ?
C16 C15 C20 C19 2.2(3) . . . . ?
N2 C15 C20 C19 -171.29(17) . . . . ?
C16 C15 C20 C22 -178.41(18) . . . . ?
N2 C15 C20 C22 8.1(3) . . . . ?

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.044

_shelxl_version_number           2014-3

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'C 2/c'
_symmetry_int_tables_number      15
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_II
_database_code_depnum_ccdc_archive 'CCDC 1853543'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         '2(C23 H26 N2), H2 O'
_chemical_formula_sum            'C46 H54 N4 O'
_chemical_melting_point          ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         678.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_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.
;

_cell_length_a                   10.7581(8)
_cell_length_b                   11.5604(9)
_cell_length_c                   16.0156(12)
_cell_angle_alpha                81.266(4)
_cell_angle_beta                 88.811(4)
_cell_angle_gamma                86.331(5)
_cell_volume                     1964.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6229
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      24.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_F_000             732
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   'SADABS, (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43215
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.573
_diffrn_reflns_theta_max         26.471
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             8056
_reflns_number_gt                5304
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²+0.2596P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8056
_refine_ls_number_parameters     484
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1285
_refine_ls_wR_factor_gt          0.1153
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
N1A N 0.99255(14) 0.02745(12) 0.21855(9) 0.0253(3) Uani 1 1 d . . . . .
N2A N 0.90238(13) 0.23249(12) 0.10651(9) 0.0259(3) Uani 1 1 d . . . . .
C2A C 1.06397(15) 0.11770(15) 0.18542(10) 0.0261(4) Uani 1 1 d . . . . .
C3A C 1.18361(16) 0.08773(16) 0.21385(11) 0.0320(4) Uani 1 1 d . . . . .
H3A H 1.253662 0.133641 0.201322 0.038 Uiso 1 1 calc R U . . .
C4A C 1.18358(16) -0.02188(16) 0.26426(11) 0.0331(4) Uani 1 1 d . . . . .
H4A H 1.253603 -0.063858 0.292042 0.040 Uiso 1 1 calc R U . . .
C5A C 1.06350(16) -0.05860(15) 0.26659(11) 0.0282(4) Uani 1 1 d . . . . .
C6A C 1.01584(16) 0.21825(14) 0.12941(10) 0.0259(4) Uani 1 1 d . . . . .
H6A H 1.070997 0.277103 0.108331 0.031 Uiso 1 1 calc R U . . .
C7A C 1.01141(16) -0.16595(15) 0.30969(11) 0.0295(4) Uani 1 1 d . . . . .
C8A C 1.09037(19) -0.25956(16) 0.34593(12) 0.0376(5) Uani 1 1 d . . . . .
H8A H 1.178031 -0.253453 0.342490 0.045 Uiso 1 1 calc R U . . .
C9A C 1.0420(2) -0.36151(17) 0.38697(13) 0.0452(5) Uani 1 1 d . . . . .
H9A H 1.096892 -0.424724 0.411307 0.054 Uiso 1 1 calc R U . . .
C10A C 0.9155(2) -0.37218(17) 0.39284(12) 0.0437(5) Uani 1 1 d . . . . .
H10A H 0.883062 -0.442120 0.421432 0.052 Uiso 1 1 calc R U . . .
C11A C 0.8363(2) -0.28082(18) 0.35701(13) 0.0453(5) Uani 1 1 d . . . . .
H11A H 0.748757 -0.287889 0.360528 0.054 Uiso 1 1 calc R U . . .
C12A C 0.88368(18) -0.17851(16) 0.31579(12) 0.0376(5) Uani 1 1 d . . . . .
H12A H 0.828061 -0.115978 0.291316 0.045 Uiso 1 1 calc R U . . .
C13A C 0.86222(15) 0.33467(14) 0.04932(11) 0.0247(4) Uani 1 1 d . . . . .
C14A C 0.86844(15) 0.33296(14) -0.03806(11) 0.0262(4) Uani 1 1 d . . . . .
C15A C 0.82216(16) 0.43315(15) -0.09020(11) 0.0294(4) Uani 1 1 d . . . . .
H15A H 0.826287 0.435434 -0.149737 0.035 Uiso 1 1 calc R U . . .
C16A C 0.77027(16) 0.52956(15) -0.05742(12) 0.0319(4) Uani 1 1 d . . . . .
H16A H 0.740378 0.597281 -0.094432 0.038 Uiso 1 1 calc R U . . .
C17A C 0.76182(16) 0.52763(15) 0.02891(11) 0.0301(4) Uani 1 1 d . . . . .
H17A H 0.724878 0.593780 0.050816 0.036 Uiso 1 1 calc R U . . .
C18A C 0.80666(15) 0.43018(14) 0.08416(11) 0.0265(4) Uani 1 1 d . . . . .
C19A C 0.91580(17) 0.22721(15) -0.07871(11) 0.0322(4) Uani 1 1 d . . . . .
H19A H 0.895399 0.247418 -0.140031 0.039 Uiso 1 1 calc R U . . .
C20A C 0.79417(18) 0.42464(16) 0.17926(11) 0.0343(4) Uani 1 1 d . . . . .
H20A H 0.786800 0.340499 0.203878 0.041 Uiso 1 1 calc R U . . .
C21A C 0.84976(18) 0.11591(16) -0.04672(13) 0.0393(5) Uani 1 1 d . . . . .
H21A H 0.874197 0.086879 0.011693 0.059 Uiso 1 1 calc R U . . .
H21B H 0.873211 0.056048 -0.082375 0.059 Uiso 1 1 calc R U . . .
H21C H 0.759415 0.133260 -0.048902 0.059 Uiso 1 1 calc R U . . .
C22A C 1.05733(17) 0.20335(17) -0.07489(13) 0.0394(5) Uani 1 1 d . . . . .
H22A H 1.097920 0.276848 -0.092222 0.059 Uiso 1 1 calc R U . . .
H22B H 1.083345 0.147326 -0.113014 0.059 Uiso 1 1 calc R U . . .
H22C H 1.081332 0.170619 -0.017003 0.059 Uiso 1 1 calc R U . . .
C23A C 0.6788(2) 0.4926(2) 0.20635(15) 0.0633(7) Uani 1 1 d . . . . .
H23A H 0.685381 0.576461 0.186411 0.095 Uiso 1 1 calc R U . . .
H23B H 0.671499 0.479393 0.268112 0.095 Uiso 1 1 calc R U . . .
H23C H 0.604852 0.465892 0.182003 0.095 Uiso 1 1 calc R U . . .
C24A C 0.9099(2) 0.46566(19) 0.21714(13) 0.0496(6) Uani 1 1 d . . . . .
H24A H 0.983618 0.418785 0.201874 0.074 Uiso 1 1 calc R U . . .
H24B H 0.900892 0.456007 0.278788 0.074 Uiso 1 1 calc R U . . .
H24C H 0.919228 0.548504 0.195059 0.074 Uiso 1 1 calc R U . . .
N1B N 0.54084(13) -0.07609(13) 0.23879(10) 0.0286(3) Uani 1 1 d . . . . .
N2B N 0.58408(13) 0.11448(12) 0.32946(9) 0.0280(3) Uani 1 1 d . . . . .
C2B C 0.51809(15) -0.07757(15) 0.32361(11) 0.0291(4) Uani 1 1 d . . . . .
C3B C 0.47299(16) -0.18512(16) 0.35414(13) 0.0356(4) Uani 1 1 d . . . . .
H3B H 0.449130 -0.211557 0.410931 0.043 Uiso 1 1 calc R U . . .
C4B C 0.46873(16) -0.24811(16) 0.28663(13) 0.0362(5) Uani 1 1 d . . . . .
H4B H 0.441543 -0.325223 0.289549 0.043 Uiso 1 1 calc R U . . .
C5B C 0.51110(15) -0.17869(14) 0.21428(12) 0.0289(4) Uani 1 1 d . . . . .
C6B C 0.53731(15) 0.02037(15) 0.36552(11) 0.0301(4) Uani 1 1 d . . . . .
H6B H 0.514053 0.015332 0.423449 0.036 Uiso 1 1 calc R U . . .
C7B C 0.52380(15) -0.19741(15) 0.12576(12) 0.0310(4) Uani 1 1 d . . . . .
C8B C 0.45928(17) -0.28358(17) 0.09677(13) 0.0385(5) Uani 1 1 d . . . . .
H8B H 0.410695 -0.333452 0.135239 0.046 Uiso 1 1 calc R U . . .
C9B C 0.46508(18) -0.29735(18) 0.01296(14) 0.0459(5) Uani 1 1 d . . . . .
H9B H 0.420438 -0.356599 -0.005933 0.055 Uiso 1 1 calc R U . . .
C10B C 0.53515(19) -0.22588(18) -0.04392(14) 0.0450(5) Uani 1 1 d . . . . .
H10B H 0.537702 -0.234978 -0.101910 0.054 Uiso 1 1 calc R U . . .
C11B C 0.60161(19) -0.14097(18) -0.01604(13) 0.0449(5) Uani 1 1 d . . . . .
H11B H 0.650805 -0.092031 -0.054733 0.054 Uiso 1 1 calc R U . . .
C12B C 0.59636(18) -0.12742(17) 0.06819(13) 0.0390(5) Uani 1 1 d . . . . .
H12B H 0.642932 -0.069484 0.087121 0.047 Uiso 1 1 calc R U . . .
C13B C 0.59924(16) 0.20963(15) 0.37481(10) 0.0278(4) Uani 1 1 d . . . . .
C14B C 0.71804(16) 0.22289(15) 0.40539(11) 0.0294(4) Uani 1 1 d . . . . .
C15B C 0.73592(18) 0.32137(17) 0.44240(12) 0.0356(4) Uani 1 1 d . . . . .
H15B H 0.815351 0.331084 0.464295 0.043 Uiso 1 1 calc R U . . .
C16B C 0.64057(18) 0.40548(17) 0.44802(12) 0.0400(5) Uani 1 1 d . . . . .
H16B H 0.654809 0.472868 0.472971 0.048 Uiso 1 1 calc R U . . .
C17B C 0.52511(18) 0.39167(17) 0.41751(12) 0.0387(5) Uani 1 1 d . . . . .
H17B H 0.460026 0.450063 0.421838 0.046 Uiso 1 1 calc R U . . .
C18B C 0.50097(17) 0.29460(16) 0.38050(12) 0.0335(4) Uani 1 1 d . . . . .
C19B C 0.82239(16) 0.12954(16) 0.40020(12) 0.0338(4) Uani 1 1 d . . . . .
H19B H 0.807388 0.091891 0.349383 0.041 Uiso 1 1 calc R U . . .
C20B C 0.37252(18) 0.28307(19) 0.34668(15) 0.0473(5) Uani 1 1 d . . . . .
H20B H 0.376190 0.211573 0.318328 0.057 Uiso 1 1 calc R U . . .
C21B C 0.95099(17) 0.17870(18) 0.38961(13) 0.0417(5) Uani 1 1 d . . . . .
H21D H 0.950631 0.241961 0.341348 0.063 Uiso 1 1 calc R U . . .
H21E H 1.013024 0.116254 0.379714 0.063 Uiso 1 1 calc R U . . .
H21F H 0.971912 0.209465 0.440965 0.063 Uiso 1 1 calc R U . . .
C22B C 0.8189(2) 0.03475(18) 0.47719(14) 0.0491(5) Uani 1 1 d . . . . .
H22D H 0.834591 0.068791 0.528120 0.074 Uiso 1 1 calc R U . . .
H22E H 0.883076 -0.027608 0.471152 0.074 Uiso 1 1 calc R U . . .
H22F H 0.736795 0.002031 0.481871 0.074 Uiso 1 1 calc R U . . .
C23B C 0.3295(3) 0.3858(3) 0.28290(19) 0.1006(12) Uani 1 1 d . . . . .
H23D H 0.250168 0.370171 0.259166 0.151 Uiso 1 1 calc R U . . .
H23E H 0.391972 0.398379 0.237533 0.151 Uiso 1 1 calc R U . . .
H23F H 0.318373 0.456066 0.310327 0.151 Uiso 1 1 calc R U . . .
C24B C 0.2783(2) 0.2668(3) 0.4167(2) 0.1059(13) Uani 1 1 d . . . . .
H24D H 0.308922 0.203881 0.460906 0.159 Uiso 1 1 calc R U . . .
H24E H 0.199778 0.245847 0.394695 0.159 Uiso 1 1 calc R U . . .
H24F H 0.264331 0.339833 0.440510 0.159 Uiso 1 1 calc R U . . .
O1 O 0.72603(12) 0.08277(11) 0.18130(9) 0.0300(3) Uani 1 1 d . . . . .
H1A H 0.9152(17) 0.0294(14) 0.2097(11) 0.024(5) Uiso 1 1 d . . . . .
H1B H 0.5781(19) -0.0188(18) 0.2056(13) 0.049(6) Uiso 1 1 d . . . . .
H1 H 0.768(2) 0.141(2) 0.1488(16) 0.072(8) Uiso 1 1 d . . . . .
H2 H 0.688(2) 0.1128(19) 0.2250(15) 0.059(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C5A 1.363(2) . ?
N1A C2A 1.370(2) . ?
N1A H1A 0.845(18) . ?
N2A C6A 1.275(2) . ?
N2A C13A 1.429(2) . ?
C2A C3A 1.380(2) . ?
C2A C6A 1.432(2) . ?
C3A C4A 1.395(2) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.383(2) . ?
C4A H4A 0.9500 . ?
C5A C7A 1.464(2) . ?
C6A H6A 0.9500 . ?
C7A C12A 1.391(3) . ?
C7A C8A 1.393(2) . ?
C8A C9A 1.386(3) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.374(3) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.376(3) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.386(3) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
C13A C14A 1.403(2) . ?
C13A C18A 1.406(2) . ?
C14A C15A 1.392(2) . ?
C14A C19A 1.525(2) . ?
C15A C16A 1.384(2) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.381(2) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.389(2) . ?
C17A H17A 0.9500 . ?
C18A C20A 1.518(2) . ?
C19A C21A 1.525(2) . ?
C19A C22A 1.531(3) . ?
C19A H19A 1.0000 . ?
C20A C23A 1.518(3) . ?
C20A C24A 1.528(3) . ?
C20A H20A 1.0000 . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
C22A H22A 0.9800 . ?
C22A H22B 0.9800 . ?
C22A H22C 0.9800 . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C23A H23C 0.9800 . ?
C24A H24A 0.9800 . ?
C24A H24B 0.9800 . ?
C24A H24C 0.9800 . ?
N1B C5B 1.363(2) . ?
N1B C2B 1.373(2) . ?
N1B H1B 0.89(2) . ?
N2B C6B 1.280(2) . ?
N2B C13B 1.426(2) . ?
C2B C3B 1.380(2) . ?
C2B C6B 1.429(2) . ?
C3B C4B 1.395(3) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.392(3) . ?
C4B H4B 0.9500 . ?
C5B C7B 1.469(3) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.390(3) . ?
C7B C12B 1.392(3) . ?
C8B C9B 1.375(3) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.380(3) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.382(3) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.381(3) . ?
C11B H11B 0.9500 . ?
C12B H12B 0.9500 . ?
C13B C14B 1.404(2) . ?
C13B C18B 1.408(2) . ?
C14B C15B 1.386(3) . ?
C14B C19B 1.517(2) . ?
C15B C16B 1.379(3) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.372(3) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.387(3) . ?
C17B H17B 0.9500 . ?
C18B C20B 1.516(3) . ?
C19B C22B 1.522(3) . ?
C19B C21B 1.525(3) . ?
C19B H19B 1.0000 . ?
C20B C24B 1.495(4) . ?
C20B C23B 1.500(3) . ?
C20B H20B 1.0000 . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?
C22B H22D 0.9800 . ?
C22B H22E 0.9800 . ?
C22B H22F 0.9800 . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?
C24B H24D 0.9800 . ?
C24B H24E 0.9800 . ?
C24B H24F 0.9800 . ?
O1 H1 0.92(3) . ?
O1 H2 0.91(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5A N1A C2A 110.41(15) . . ?
C5A N1A H1A 127.7(12) . . ?
C2A N1A H1A 121.9(12) . . ?
C6A N2A C13A 119.54(14) . . ?
N1A C2A C3A 106.85(15) . . ?
N1A C2A C6A 123.02(15) . . ?
C3A C2A C6A 130.08(16) . . ?
C2A C3A C4A 107.95(15) . . ?
C2A C3A H3A 126.0 . . ?
C4A C3A H3A 126.0 . . ?
C5A C4A C3A 107.87(15) . . ?
C5A C4A H4A 126.1 . . ?
C3A C4A H4A 126.1 . . ?
N1A C5A C4A 106.92(15) . . ?
N1A C5A C7A 122.26(15) . . ?
C4A C5A C7A 130.82(16) . . ?
N2A C6A C2A 123.05(15) . . ?
N2A C6A H6A 118.5 . . ?
C2A C6A H6A 118.5 . . ?
C12A C7A C8A 118.00(17) . . ?
C12A C7A C5A 121.95(16) . . ?
C8A C7A C5A 120.05(16) . . ?
C9A C8A C7A 120.50(19) . . ?
C9A C8A H8A 119.8 . . ?
C7A C8A H8A 119.8 . . ?
C10A C9A C8A 120.74(19) . . ?
C10A C9A H9A 119.6 . . ?
C8A C9A H9A 119.6 . . ?
C9A C10A C11A 119.51(19) . . ?
C9A C10A H10A 120.2 . . ?
C11A C10A H10A 120.2 . . ?
C10A C11A C12A 120.2(2) . . ?
C10A C11A H11A 119.9 . . ?
C12A C11A H11A 119.9 . . ?
C11A C12A C7A 121.03(18) . . ?
C11A C12A H12A 119.5 . . ?
C7A C12A H12A 119.5 . . ?
C14A C13A C18A 122.35(15) . . ?
C14A C13A N2A 119.86(14) . . ?
C18A C13A N2A 117.52(15) . . ?
C15A C14A C13A 117.05(15) . . ?
C15A C14A C19A 118.45(16) . . ?
C13A C14A C19A 124.42(15) . . ?
C16A C15A C14A 121.58(17) . . ?
C16A C15A H15A 119.2 . . ?
C14A C15A H15A 119.2 . . ?
C17A C16A C15A 120.21(16) . . ?
C17A C16A H16A 119.9 . . ?
C15A C16A H16A 119.9 . . ?
C16A C17A C18A 120.83(16) . . ?
C16A C17A H17A 119.6 . . ?
C18A C17A H17A 119.6 . . ?
C17A C18A C13A 117.89(16) . . ?
C17A C18A C20A 121.63(16) . . ?
C13A C18A C20A 120.46(15) . . ?
C21A C19A C14A 113.79(15) . . ?
C21A C19A C22A 110.74(15) . . ?
C14A C19A C22A 113.77(15) . . ?
C21A C19A H19A 105.9 . . ?
C14A C19A H19A 105.9 . . ?
C22A C19A H19A 105.9 . . ?
C23A C20A C18A 113.33(16) . . ?
C23A C20A C24A 109.79(18) . . ?
C18A C20A C24A 111.72(15) . . ?
C23A C20A H20A 107.2 . . ?
C18A C20A H20A 107.2 . . ?
C24A C20A H20A 107.2 . . ?
C19A C21A H21A 109.5 . . ?
C19A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C19A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C19A C22A H22A 109.5 . . ?
C19A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C19A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
C20A C23A H23A 109.5 . . ?
C20A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
C20A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
C20A C24A H24A 109.5 . . ?
C20A C24A H24B 109.5 . . ?
H24A C24A H24B 109.5 . . ?
C20A C24A H24C 109.5 . . ?
H24A C24A H24C 109.5 . . ?
H24B C24A H24C 109.5 . . ?
C5B N1B C2B 110.86(15) . . ?
C5B N1B H1B 124.6(14) . . ?
C2B N1B H1B 124.2(14) . . ?
C6B N2B C13B 120.82(15) . . ?
N1B C2B C3B 106.89(16) . . ?
N1B C2B C6B 122.64(16) . . ?
C3B C2B C6B 130.45(17) . . ?
C2B C3B C4B 107.72(17) . . ?
C2B C3B H3B 126.1 . . ?
C4B C3B H3B 126.1 . . ?
C5B C4B C3B 108.34(16) . . ?
C5B C4B H4B 125.8 . . ?
C3B C4B H4B 125.8 . . ?
N1B C5B C4B 106.19(16) . . ?
N1B C5B C7B 121.30(16) . . ?
C4B C5B C7B 132.49(16) . . ?
N2B C6B C2B 123.72(16) . . ?
N2B C6B H6B 118.1 . . ?
C2B C6B H6B 118.1 . . ?
C8B C7B C12B 118.30(18) . . ?
C8B C7B C5B 120.26(17) . . ?
C12B C7B C5B 121.40(16) . . ?
C9B C8B C7B 120.65(19) . . ?
C9B C8B H8B 119.7 . . ?
C7B C8B H8B 119.7 . . ?
C8B C9B C10B 120.59(19) . . ?
C8B C9B H9B 119.7 . . ?
C10B C9B H9B 119.7 . . ?
C9B C10B C11B 119.6(2) . . ?
C9B C10B H10B 120.2 . . ?
C11B C10B H10B 120.2 . . ?
C12B C11B C10B 119.9(2) . . ?
C12B C11B H11B 120.1 . . ?
C10B C11B H11B 120.1 . . ?
C11B C12B C7B 120.97(18) . . ?
C11B C12B H12B 119.5 . . ?
C7B C12B H12B 119.5 . . ?
C14B C13B C18B 121.05(16) . . ?
C14B C13B N2B 118.13(15) . . ?
C18B C13B N2B 120.46(15) . . ?
C15B C14B C13B 118.27(16) . . ?
C15B C14B C19B 121.27(16) . . ?
C13B C14B C19B 120.44(15) . . ?
C16B C15B C14B 121.23(17) . . ?
C16B C15B H15B 119.4 . . ?
C14B C15B H15B 119.4 . . ?
C17B C16B C15B 119.87(18) . . ?
C17B C16B H16B 120.1 . . ?
C15B C16B H16B 120.1 . . ?
C16B C17B C18B 121.67(18) . . ?
C16B C17B H17B 119.2 . . ?
C18B C17B H17B 119.2 . . ?
C17B C18B C13B 117.90(17) . . ?
C17B C18B C20B 120.12(17) . . ?
C13B C18B C20B 121.97(16) . . ?
C14B C19B C22B 110.34(15) . . ?
C14B C19B C21B 113.26(15) . . ?
C22B C19B C21B 110.48(16) . . ?
C14B C19B H19B 107.5 . . ?
C22B C19B H19B 107.5 . . ?
C21B C19B H19B 107.5 . . ?
C24B C20B C23B 109.0(2) . . ?
C24B C20B C18B 111.11(19) . . ?
C23B C20B C18B 113.06(19) . . ?
C24B C20B H20B 107.8 . . ?
C23B C20B H20B 107.8 . . ?
C18B C20B H20B 107.8 . . ?
C19B C21B H21D 109.5 . . ?
C19B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C19B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C19B C22B H22D 109.5 . . ?
C19B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C19B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
C20B C23B H23D 109.5 . . ?
C20B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
C20B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
C20B C24B H24D 109.5 . . ?
C20B C24B H24E 109.5 . . ?
H24D C24B H24E 109.5 . . ?
C20B C24B H24F 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?
H1 O1 H2 109(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
C5A N1A C2A C3A -0.29(19) . . . . ?
C5A N1A C2A C6A 177.32(15) . . . . ?
N1A C2A C3A C4A 0.23(19) . . . . ?
C6A C2A C3A C4A -177.14(17) . . . . ?
C2A C3A C4A C5A -0.1(2) . . . . ?
C2A N1A C5A C4A 0.23(19) . . . . ?
C2A N1A C5A C7A -179.87(15) . . . . ?
C3A C4A C5A N1A -0.1(2) . . . . ?
C3A C4A C5A C7A -179.97(17) . . . . ?
C13A N2A C6A C2A -179.05(15) . . . . ?
N1A C2A C6A N2A 0.7(3) . . . . ?
C3A C2A C6A N2A 177.72(17) . . . . ?
N1A C5A C7A C12A -10.7(3) . . . . ?
C4A C5A C7A C12A 169.14(19) . . . . ?
N1A C5A C7A C8A 169.08(17) . . . . ?
C4A C5A C7A C8A -11.1(3) . . . . ?
C12A C7A C8A C9A -0.3(3) . . . . ?
C5A C7A C8A C9A 179.92(17) . . . . ?
C7A C8A C9A C10A -0.1(3) . . . . ?
C8A C9A C10A C11A 0.5(3) . . . . ?
C9A C10A C11A C12A -0.4(3) . . . . ?
C10A C11A C12A C7A 0.0(3) . . . . ?
C8A C7A C12A C11A 0.3(3) . . . . ?
C5A C7A C12A C11A -179.88(17) . . . . ?
C6A N2A C13A C14A 89.69(19) . . . . ?
C6A N2A C13A C18A -96.17(18) . . . . ?
C18A C13A C14A C15A 3.0(2) . . . . ?
N2A C13A C14A C15A 176.87(14) . . . . ?
C18A C13A C14A C19A -173.63(15) . . . . ?
N2A C13A C14A C19A 0.2(2) . . . . ?
C13A C14A C15A C16A -1.1(2) . . . . ?
C19A C14A C15A C16A 175.76(16) . . . . ?
C14A C15A C16A C17A -0.8(3) . . . . ?
C15A C16A C17A C18A 1.0(3) . . . . ?
C16A C17A C18A C13A 0.9(2) . . . . ?
C16A C17A C18A C20A -177.82(16) . . . . ?
C14A C13A C18A C17A -2.9(2) . . . . ?
N2A C13A C18A C17A -176.90(14) . . . . ?
C14A C13A C18A C20A 175.77(15) . . . . ?
N2A C13A C18A C20A 1.8(2) . . . . ?
C15A C14A C19A C21A -122.14(17) . . . . ?
C13A C14A C19A C21A 54.5(2) . . . . ?
C15A C14A C19A C22A 109.75(18) . . . . ?
C13A C14A C19A C22A -73.6(2) . . . . ?
C17A C18A C20A C23A 31.1(2) . . . . ?
C13A C18A C20A C23A -147.55(18) . . . . ?
C17A C18A C20A C24A -93.6(2) . . . . ?
C13A C18A C20A C24A 87.8(2) . . . . ?
C5B N1B C2B C3B 0.35(19) . . . . ?
C5B N1B C2B C6B -177.99(15) . . . . ?
N1B C2B C3B C4B -0.1(2) . . . . ?
C6B C2B C3B C4B 178.05(17) . . . . ?
C2B C3B C4B C5B -0.2(2) . . . . ?
C2B N1B C5B C4B -0.45(19) . . . . ?
C2B N1B C5B C7B 178.25(15) . . . . ?
C3B C4B C5B N1B 0.4(2) . . . . ?
C3B C4B C5B C7B -178.12(18) . . . . ?
C13B N2B C6B C2B 179.19(15) . . . . ?
N1B C2B C6B N2B -4.4(3) . . . . ?
C3B C2B C6B N2B 177.68(18) . . . . ?
N1B C5B C7B C8B -160.05(16) . . . . ?
C4B C5B C7B C8B 18.2(3) . . . . ?
N1B C5B C7B C12B 17.6(3) . . . . ?
C4B C5B C7B C12B -164.12(19) . . . . ?
C12B C7B C8B C9B -1.4(3) . . . . ?
C5B C7B C8B C9B 176.32(17) . . . . ?
C7B C8B C9B C10B 0.0(3) . . . . ?
C8B C9B C10B C11B 1.0(3) . . . . ?
C9B C10B C11B C12B -0.7(3) . . . . ?
C10B C11B C12B C7B -0.7(3) . . . . ?
C8B C7B C12B C11B 1.7(3) . . . . ?
C5B C7B C12B C11B -175.97(17) . . . . ?
C6B N2B C13B C14B 100.34(19) . . . . ?
C6B N2B C13B C18B -86.4(2) . . . . ?
C18B C13B C14B C15B 0.8(3) . . . . ?
N2B C13B C14B C15B 173.96(16) . . . . ?
C18B C13B C14B C19B 178.93(16) . . . . ?
N2B C13B C14B C19B -7.9(2) . . . . ?
C13B C14B C15B C16B -1.1(3) . . . . ?
C19B C14B C15B C16B -179.20(17) . . . . ?
C14B C15B C16B C17B 0.8(3) . . . . ?
C15B C16B C17B C18B -0.2(3) . . . . ?
C16B C17B C18B C13B -0.1(3) . . . . ?
C16B C17B C18B C20B -179.35(19) . . . . ?
C14B C13B C18B C17B -0.2(3) . . . . ?
N2B C13B C18B C17B -173.23(16) . . . . ?
C14B C13B C18B C20B 179.02(17) . . . . ?
N2B C13B C18B C20B 6.0(3) . . . . ?
C15B C14B C19B C22B 91.4(2) . . . . ?
C13B C14B C19B C22B -86.7(2) . . . . ?
C15B C14B C19B C21B -33.1(2) . . . . ?
C13B C14B C19B C21B 148.85(17) . . . . ?
C17B C18B C20B C24B -66.9(3) . . . . ?
C13B C18B C20B C24B 113.9(2) . . . . ?
C17B C18B C20B C23B 56.0(3) . . . . ?
C13B C18B C20B C23B -123.2(2) . . . . ?

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_IIA
_database_code_depnum_ccdc_archive 'CCDC 1853544'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         '2(C23 H26 N2), H2 O'
_chemical_formula_sum            'C46 H54 N4 O'
_chemical_melting_point          ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Brown
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         678.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   13.5296(4)
_cell_length_b                   15.0823(5)
_cell_length_c                   19.7874(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4037.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9953
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      24.81
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_F_000             1464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39980
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.698
_diffrn_reflns_theta_max         25.740
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7652
_reflns_number_gt                6370
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.995

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2458 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         7652
_refine_ls_number_parameters     484
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0770
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.017
_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
O1 O 0.20199(11) 1.07531(10) 0.50643(7) 0.0284(3) Uani 1 1 d D . . . .
N1A N 0.24982(13) 0.89439(12) 0.45955(8) 0.0248(4) Uani 1 1 d . . . . .
N2A N 0.06645(12) 0.93895(11) 0.53338(8) 0.0250(4) Uani 1 1 d . . . . .
C2A C 0.17716(15) 0.83591(14) 0.47894(9) 0.0272(5) Uani 1 1 d . . . . .
C3A C 0.20809(17) 0.75248(15) 0.46057(11) 0.0351(5) Uani 1 1 d . . . . .
H3A H 0.172683 0.698819 0.467360 0.042 Uiso 1 1 calc R U . . .
C4A C 0.30069(17) 0.76061(15) 0.43018(10) 0.0334(5) Uani 1 1 d . . . . .
H4A H 0.339616 0.713467 0.412709 0.040 Uiso 1 1 calc R U . . .
C5A C 0.32572(16) 0.84946(14) 0.43002(9) 0.0259(5) Uani 1 1 d . . . . .
C6A C 0.08908(15) 0.86034(14) 0.51423(9) 0.0275(5) Uani 1 1 d . . . . .
H6A H 0.043411 0.814374 0.524352 0.033 Uiso 1 1 calc R U . . .
C7A C 0.41617(15) 0.89250(14) 0.40706(9) 0.0270(5) Uani 1 1 d . . . . .
C8A C 0.49077(17) 0.84172(16) 0.37810(11) 0.0370(6) Uani 1 1 d . . . . .
H8A H 0.480959 0.779870 0.371966 0.044 Uiso 1 1 calc R U . . .
C9A C 0.57847(19) 0.87958(17) 0.35820(12) 0.0445(6) Uani 1 1 d . . . . .
H9A H 0.628664 0.843691 0.338738 0.053 Uiso 1 1 calc R U . . .
C10A C 0.59414(18) 0.96953(18) 0.36633(11) 0.0414(6) Uani 1 1 d . . . . .
H10A H 0.654815 0.995502 0.352462 0.050 Uiso 1 1 calc R U . . .
C11A C 0.52119(18) 1.02122(16) 0.39466(11) 0.0389(6) Uani 1 1 d . . . . .
H11A H 0.531508 1.083046 0.400553 0.047 Uiso 1 1 calc R U . . .
C12A C 0.43244(17) 0.98288(15) 0.41463(10) 0.0337(5) Uani 1 1 d . . . . .
H12A H 0.382177 1.019020 0.433741 0.040 Uiso 1 1 calc R U . . .
C13A C -0.02505(15) 0.94838(13) 0.56894(9) 0.0235(5) Uani 1 1 d . . . . .
C14A C -0.10827(16) 0.97693(13) 0.53335(10) 0.0267(5) Uani 1 1 d . . . . .
C15A C -0.19718(17) 0.98343(14) 0.56771(11) 0.0333(5) Uani 1 1 d . . . . .
H15A H -0.254862 1.002056 0.544297 0.040 Uiso 1 1 calc R U . . .
C16A C -0.20282(17) 0.96317(15) 0.63546(12) 0.0361(6) Uani 1 1 d . . . . .
H16A H -0.264758 0.965887 0.657987 0.043 Uiso 1 1 calc R U . . .
C17A C -0.11944(17) 0.93900(15) 0.67081(11) 0.0352(6) Uani 1 1 d . . . . .
H17A H -0.124243 0.927246 0.717867 0.042 Uiso 1 1 calc R U . . .
C18A C -0.02817(16) 0.93148(14) 0.63879(10) 0.0288(5) Uani 1 1 d . . . . .
C19A C -0.10002(18) 0.99815(15) 0.45851(10) 0.0362(6) Uani 1 1 d . . . . .
H19A H -0.030044 1.015988 0.449578 0.043 Uiso 1 1 calc R U . . .
C20A C -0.1214(2) 0.91615(17) 0.41559(11) 0.0506(7) Uani 1 1 d . . . . .
H20A H -0.190266 0.897973 0.422094 0.076 Uiso 1 1 calc R U . . .
H20B H -0.077359 0.867799 0.429317 0.076 Uiso 1 1 calc R U . . .
H20C H -0.110213 0.930096 0.367822 0.076 Uiso 1 1 calc R U . . .
C21A C -0.1658(2) 1.07506(17) 0.43693(12) 0.0525(7) Uani 1 1 d . . . . .
H21A H -0.151489 1.126934 0.465105 0.079 Uiso 1 1 calc R U . . .
H21B H -0.235305 1.058273 0.442349 0.079 Uiso 1 1 calc R U . . .
H21C H -0.152857 1.089449 0.389449 0.079 Uiso 1 1 calc R U . . .
C22A C 0.06587(17) 0.91317(16) 0.67819(10) 0.0387(6) Uani 1 1 d . . . . .
H22A H 0.112801 0.881688 0.647396 0.046 Uiso 1 1 calc R U . . .
C23A C 0.1129(2) 1.00046(19) 0.69833(14) 0.0600(8) Uani 1 1 d . . . . .
H23A H 0.174095 0.988916 0.723366 0.090 Uiso 1 1 calc R U . . .
H23B H 0.067105 1.033916 0.726967 0.090 Uiso 1 1 calc R U . . .
H23C H 0.128057 1.034980 0.657660 0.090 Uiso 1 1 calc R U . . .
C24A C 0.0512(2) 0.85552(18) 0.74064(11) 0.0522(7) Uani 1 1 d . . . . .
H24A H 0.011686 0.887863 0.774013 0.078 Uiso 1 1 calc R U . . .
H24B H 0.115754 0.840811 0.760172 0.078 Uiso 1 1 calc R U . . .
H24C H 0.016882 0.800818 0.727900 0.078 Uiso 1 1 calc R U . . .
N1B N 0.34312(14) 1.20568(11) 0.46237(8) 0.0241(4) Uani 1 1 d . . . . .
N2B N 0.35889(12) 1.12208(11) 0.59269(8) 0.0249(4) Uani 1 1 d . . . . .
C2B C 0.42732(15) 1.20491(13) 0.50089(10) 0.0255(5) Uani 1 1 d . . . . .
C3B C 0.49592(17) 1.25638(15) 0.46769(10) 0.0330(5) Uani 1 1 d . . . . .
H3B H 0.561527 1.267855 0.482396 0.040 Uiso 1 1 calc R U . . .
C4B C 0.45240(17) 1.28879(15) 0.40867(10) 0.0330(5) Uani 1 1 d . . . . .
H4B H 0.482857 1.326342 0.376232 0.040 Uiso 1 1 calc R U . . .
C5B C 0.35684(16) 1.25628(13) 0.40600(9) 0.0257(5) Uani 1 1 d . . . . .
C6B C 0.43196(16) 1.16286(13) 0.56568(9) 0.0262(5) Uani 1 1 d . . . . .
H6B H 0.492478 1.165339 0.589950 0.031 Uiso 1 1 calc R U . . .
C7B C 0.27654(16) 1.27186(13) 0.35788(9) 0.0255(5) Uani 1 1 d . . . . .
C8B C 0.28788(17) 1.33399(15) 0.30666(10) 0.0342(5) Uani 1 1 d . . . . .
H8B H 0.349334 1.363703 0.301532 0.041 Uiso 1 1 calc R U . . .
C9B C 0.21132(19) 1.35312(17) 0.26322(11) 0.0421(6) Uani 1 1 d . . . . .
H9B H 0.220490 1.395990 0.228606 0.050 Uiso 1 1 calc R U . . .
C10B C 0.12114(19) 1.31058(17) 0.26942(11) 0.0406(6) Uani 1 1 d . . . . .
H10B H 0.067985 1.324811 0.239982 0.049 Uiso 1 1 calc R U . . .
C11B C 0.10969(17) 1.24718(16) 0.31905(10) 0.0367(6) Uani 1 1 d . . . . .
H11B H 0.048570 1.216656 0.323193 0.044 Uiso 1 1 calc R U . . .
C12B C 0.18639(17) 1.22759(15) 0.36286(10) 0.0321(5) Uani 1 1 d . . . . .
H12B H 0.177519 1.183554 0.396643 0.039 Uiso 1 1 calc R U . . .
C13B C 0.37009(15) 1.08790(14) 0.65964(9) 0.0249(5) Uani 1 1 d . . . . .
C14B C 0.39251(16) 0.99838(14) 0.66835(10) 0.0307(5) Uani 1 1 d . . . . .
C15B C 0.39795(18) 0.96617(17) 0.73364(11) 0.0406(6) Uani 1 1 d . . . . .
H15B H 0.414092 0.905577 0.740721 0.049 Uiso 1 1 calc R U . . .
C16B C 0.38050(18) 1.01993(17) 0.78876(11) 0.0431(6) Uani 1 1 d . . . . .
H16B H 0.385264 0.996481 0.833199 0.052 Uiso 1 1 calc R U . . .
C17B C 0.35616(17) 1.10763(16) 0.77918(10) 0.0360(5) Uani 1 1 d . . . . .
H17B H 0.343117 1.143998 0.817353 0.043 Uiso 1 1 calc R U . . .
C18B C 0.35028(16) 1.14404(14) 0.71484(9) 0.0284(5) Uani 1 1 d . . . . .
C19B C 0.41043(18) 0.93956(15) 0.60715(11) 0.0377(6) Uani 1 1 d . . . . .
H19B H 0.373563 0.966508 0.568459 0.045 Uiso 1 1 calc R U . . .
C20B C 0.5190(2) 0.93883(19) 0.58785(12) 0.0524(7) Uani 1 1 d . . . . .
H20D H 0.557413 0.910783 0.623973 0.079 Uiso 1 1 calc R U . . .
H20E H 0.541935 0.999858 0.581320 0.079 Uiso 1 1 calc R U . . .
H20F H 0.527648 0.905393 0.545807 0.079 Uiso 1 1 calc R U . . .
C21B C 0.3711(2) 0.84553(17) 0.61612(13) 0.0570(8) Uani 1 1 d . . . . .
H21D H 0.301575 0.847903 0.629914 0.086 Uiso 1 1 calc R U . . .
H21E H 0.409728 0.814947 0.650926 0.086 Uiso 1 1 calc R U . . .
H21F H 0.376696 0.813315 0.573277 0.086 Uiso 1 1 calc R U . . .
C22B C 0.31905(17) 1.23948(15) 0.70321(11) 0.0346(5) Uani 1 1 d . . . . .
H22B H 0.355103 1.260976 0.662252 0.042 Uiso 1 1 calc R U . . .
C23B C 0.3456(2) 1.30152(16) 0.76094(11) 0.0462(6) Uani 1 1 d . . . . .
H23D H 0.415725 1.294704 0.772082 0.069 Uiso 1 1 calc R U . . .
H23E H 0.305390 1.286940 0.800622 0.069 Uiso 1 1 calc R U . . .
H23F H 0.332664 1.362913 0.747331 0.069 Uiso 1 1 calc R U . . .
C24B C 0.2093(2) 1.24421(18) 0.68740(16) 0.0567(7) Uani 1 1 d . . . . .
H24D H 0.171504 1.222036 0.726104 0.085 Uiso 1 1 calc R U . . .
H24E H 0.194954 1.207788 0.647580 0.085 Uiso 1 1 calc R U . . .
H24F H 0.190736 1.305869 0.678302 0.085 Uiso 1 1 calc R U . . .
H1A H 0.2462(16) 0.9516(16) 0.4683(10) 0.030(6) Uiso 1 1 d . . . . .
H1B H 0.2886(17) 1.1760(15) 0.4732(10) 0.034(7) Uiso 1 1 d . . . . .
H1 H 0.244(2) 1.086(2) 0.5433(12) 0.074(9) Uiso 1 1 d D . . . .
H2 H 0.1486(19) 1.0398(18) 0.5195(14) 0.076(10) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.94(2) . ?
O1 H2 0.94(2) . ?
N1A C5A 1.362(3) . ?
N1A C2A 1.375(3) . ?
N1A H1A 0.88(2) . ?
N2A C6A 1.282(3) . ?
N2A C13A 1.431(3) . ?
C2A C3A 1.375(3) . ?
C2A C6A 1.429(3) . ?
C3A C4A 1.395(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.382(3) . ?
C4A H4A 0.9500 . ?
C5A C7A 1.458(3) . ?
C6A H6A 0.9500 . ?
C7A C12A 1.389(3) . ?
C7A C8A 1.391(3) . ?
C8A C9A 1.374(3) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.383(3) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.377(3) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.390(3) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
C13A C14A 1.396(3) . ?
C13A C18A 1.406(3) . ?
C14A C15A 1.385(3) . ?
C14A C19A 1.519(3) . ?
C15A C16A 1.377(3) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.377(3) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.393(3) . ?
C17A H17A 0.9500 . ?
C18A C22A 1.517(3) . ?
C19A C21A 1.523(3) . ?
C19A C20A 1.528(3) . ?
C19A H19A 1.0000 . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
C22A C23A 1.516(4) . ?
C22A C24A 1.524(3) . ?
C22A H22A 1.0000 . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C23A H23C 0.9800 . ?
C24A H24A 0.9800 . ?
C24A H24B 0.9800 . ?
C24A H24C 0.9800 . ?
N1B C5B 1.364(2) . ?
N1B C2B 1.371(3) . ?
N1B H1B 0.89(2) . ?
N2B C6B 1.281(3) . ?
N2B C13B 1.430(2) . ?
C2B C3B 1.377(3) . ?
C2B C6B 1.432(3) . ?
C3B C4B 1.396(3) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.384(3) . ?
C4B H4B 0.9500 . ?
C5B C7B 1.464(3) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.389(3) . ?
C7B C12B 1.394(3) . ?
C8B C9B 1.377(3) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.384(4) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.379(3) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.384(3) . ?
C11B H11B 0.9500 . ?
C12B H12B 0.9500 . ?
C13B C14B 1.395(3) . ?
C13B C18B 1.408(3) . ?
C14B C15B 1.382(3) . ?
C14B C19B 1.521(3) . ?
C15B C16B 1.379(3) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.376(3) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.389(3) . ?
C17B H17B 0.9500 . ?
C18B C22B 1.518(3) . ?
C19B C20B 1.517(4) . ?
C19B C21B 1.525(4) . ?
C19B H19B 1.0000 . ?
C20B H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 0.9800 . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?
C22B C24B 1.519(3) . ?
C22B C23B 1.519(3) . ?
C22B H22B 1.0000 . ?
C23B H23D 0.9800 . ?
C23B H23E 0.9800 . ?
C23B H23F 0.9800 . ?
C24B H24D 0.9800 . ?
C24B H24E 0.9800 . ?
C24B H24F 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
H1 O1 H2 111(2) . . ?
C5A N1A C2A 109.85(18) . . ?
C5A N1A H1A 127.8(15) . . ?
C2A N1A H1A 122.2(14) . . ?
C6A N2A C13A 116.35(17) . . ?
C3A C2A N1A 107.19(18) . . ?
C3A C2A C6A 128.22(19) . . ?
N1A C2A C6A 124.54(18) . . ?
C2A C3A C4A 107.9(2) . . ?
C2A C3A H3A 126.1 . . ?
C4A C3A H3A 126.1 . . ?
C5A C4A C3A 107.8(2) . . ?
C5A C4A H4A 126.1 . . ?
C3A C4A H4A 126.1 . . ?
N1A C5A C4A 107.26(19) . . ?
N1A C5A C7A 123.02(18) . . ?
C4A C5A C7A 129.6(2) . . ?
N2A C6A C2A 125.58(19) . . ?
N2A C6A H6A 117.2 . . ?
C2A C6A H6A 117.2 . . ?
C12A C7A C8A 118.0(2) . . ?
C12A C7A C5A 122.44(19) . . ?
C8A C7A C5A 119.5(2) . . ?
C9A C8A C7A 121.1(2) . . ?
C9A C8A H8A 119.5 . . ?
C7A C8A H8A 119.5 . . ?
C8A C9A C10A 120.5(2) . . ?
C8A C9A H9A 119.8 . . ?
C10A C9A H9A 119.8 . . ?
C11A C10A C9A 119.5(2) . . ?
C11A C10A H10A 120.2 . . ?
C9A C10A H10A 120.2 . . ?
C10A C11A C12A 120.0(2) . . ?
C10A C11A H11A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C7A C12A C11A 121.0(2) . . ?
C7A C12A H12A 119.5 . . ?
C11A C12A H12A 119.5 . . ?
C14A C13A C18A 121.84(19) . . ?
C14A C13A N2A 118.70(16) . . ?
C18A C13A N2A 119.43(18) . . ?
C15A C14A C13A 118.33(18) . . ?
C15A C14A C19A 121.83(19) . . ?
C13A C14A C19A 119.83(19) . . ?
C16A C15A C14A 120.7(2) . . ?
C16A C15A H15A 119.7 . . ?
C14A C15A H15A 119.7 . . ?
C17A C16A C15A 120.5(2) . . ?
C17A C16A H16A 119.7 . . ?
C15A C16A H16A 119.7 . . ?
C16A C17A C18A 121.14(19) . . ?
C16A C17A H17A 119.4 . . ?
C18A C17A H17A 119.4 . . ?
C17A C18A C13A 117.33(19) . . ?
C17A C18A C22A 121.64(17) . . ?
C13A C18A C22A 120.85(19) . . ?
C14A C19A C21A 113.0(2) . . ?
C14A C19A C20A 110.95(18) . . ?
C21A C19A C20A 110.49(19) . . ?
C14A C19A H19A 107.4 . . ?
C21A C19A H19A 107.4 . . ?
C20A C19A H19A 107.4 . . ?
C19A C20A H20A 109.5 . . ?
C19A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C19A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C19A C21A H21A 109.5 . . ?
C19A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C19A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C23A C22A C18A 109.2(2) . . ?
C23A C22A C24A 109.69(19) . . ?
C18A C22A C24A 114.3(2) . . ?
C23A C22A H22A 107.8 . . ?
C18A C22A H22A 107.8 . . ?
C24A C22A H22A 107.8 . . ?
C22A C23A H23A 109.5 . . ?
C22A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
C22A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
C22A C24A H24A 109.5 . . ?
C22A C24A H24B 109.5 . . ?
H24A C24A H24B 109.5 . . ?
C22A C24A H24C 109.5 . . ?
H24A C24A H24C 109.5 . . ?
H24B C24A H24C 109.5 . . ?
C5B N1B C2B 110.26(18) . . ?
C5B N1B H1B 126.2(14) . . ?
C2B N1B H1B 123.5(14) . . ?
C6B N2B C13B 118.55(17) . . ?
N1B C2B C3B 106.87(17) . . ?
N1B C2B C6B 122.56(18) . . ?
C3B C2B C6B 130.3(2) . . ?
C2B C3B C4B 108.19(19) . . ?
C2B C3B H3B 125.9 . . ?
C4B C3B H3B 125.9 . . ?
C5B C4B C3B 107.57(19) . . ?
C5B C4B H4B 126.2 . . ?
C3B C4B H4B 126.2 . . ?
N1B C5B C4B 107.11(18) . . ?
N1B C5B C7B 121.38(18) . . ?
C4B C5B C7B 131.41(19) . . ?
N2B C6B C2B 123.53(19) . . ?
N2B C6B H6B 118.2 . . ?
C2B C6B H6B 118.2 . . ?
C8B C7B C12B 118.13(19) . . ?
C8B C7B C5B 120.07(19) . . ?
C12B C7B C5B 121.78(19) . . ?
C9B C8B C7B 120.9(2) . . ?
C9B C8B H8B 119.5 . . ?
C7B C8B H8B 119.5 . . ?
C8B C9B C10B 120.7(2) . . ?
C8B C9B H9B 119.6 . . ?
C10B C9B H9B 119.6 . . ?
C11B C10B C9B 118.9(2) . . ?
C11B C10B H10B 120.5 . . ?
C9B C10B H10B 120.5 . . ?
C10B C11B C12B 120.6(2) . . ?
C10B C11B H11B 119.7 . . ?
C12B C11B H11B 119.7 . . ?
C11B C12B C7B 120.6(2) . . ?
C11B C12B H12B 119.7 . . ?
C7B C12B H12B 119.7 . . ?
C14B C13B C18B 121.85(18) . . ?
C14B C13B N2B 119.12(17) . . ?
C18B C13B N2B 118.82(17) . . ?
C15B C14B C13B 117.9(2) . . ?
C15B C14B C19B 122.1(2) . . ?
C13B C14B C19B 120.07(18) . . ?
C16B C15B C14B 121.6(2) . . ?
C16B C15B H15B 119.2 . . ?
C14B C15B H15B 119.2 . . ?
C17B C16B C15B 119.8(2) . . ?
C17B C16B H16B 120.1 . . ?
C15B C16B H16B 120.1 . . ?
C16B C17B C18B 121.3(2) . . ?
C16B C17B H17B 119.3 . . ?
C18B C17B H17B 119.3 . . ?
C17B C18B C13B 117.6(2) . . ?
C17B C18B C22B 122.00(19) . . ?
C13B C18B C22B 120.38(17) . . ?
C20B C19B C14B 111.0(2) . . ?
C20B C19B C21B 111.1(2) . . ?
C14B C19B C21B 113.22(19) . . ?
C20B C19B H19B 107.0 . . ?
C14B C19B H19B 107.0 . . ?
C21B C19B H19B 107.0 . . ?
C19B C20B H20D 109.5 . . ?
C19B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C19B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C19B C21B H21D 109.5 . . ?
C19B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C19B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
C18B C22B C24B 110.4(2) . . ?
C18B C22B C23B 113.85(19) . . ?
C24B C22B C23B 110.9(2) . . ?
C18B C22B H22B 107.1 . . ?
C24B C22B H22B 107.1 . . ?
C23B C22B H22B 107.1 . . ?
C22B C23B H23D 109.5 . . ?
C22B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
C22B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
C22B C24B H24D 109.5 . . ?
C22B C24B H24E 109.5 . . ?
H24D C24B H24E 109.5 . . ?
C22B C24B H24F 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 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
C5A N1A C2A C3A -0.5(2) . . . . ?
C5A N1A C2A C6A 177.04(17) . . . . ?
N1A C2A C3A C4A 0.4(2) . . . . ?
C6A C2A C3A C4A -177.01(19) . . . . ?
C2A C3A C4A C5A -0.2(2) . . . . ?
C2A N1A C5A C4A 0.4(2) . . . . ?
C2A N1A C5A C7A -176.87(17) . . . . ?
C3A C4A C5A N1A -0.1(2) . . . . ?
C3A C4A C5A C7A 176.88(19) . . . . ?
C13A N2A C6A C2A -179.13(17) . . . . ?
C3A C2A C6A N2A 175.9(2) . . . . ?
N1A C2A C6A N2A -1.1(3) . . . . ?
N1A C5A C7A C12A 1.1(3) . . . . ?
C4A C5A C7A C12A -175.5(2) . . . . ?
N1A C5A C7A C8A 179.24(18) . . . . ?
C4A C5A C7A C8A 2.7(3) . . . . ?
C12A C7A C8A C9A 0.7(3) . . . . ?
C5A C7A C8A C9A -177.55(19) . . . . ?
C7A C8A C9A C10A -0.3(3) . . . . ?
C8A C9A C10A C11A 0.1(4) . . . . ?
C9A C10A C11A C12A -0.2(3) . . . . ?
C8A C7A C12A C11A -0.8(3) . . . . ?
C5A C7A C12A C11A 177.37(19) . . . . ?
C10A C11A C12A C7A 0.6(3) . . . . ?
C6A N2A C13A C14A -98.5(2) . . . . ?
C6A N2A C13A C18A 83.5(2) . . . . ?
C18A C13A C14A C15A -3.9(3) . . . . ?
N2A C13A C14A C15A 178.17(18) . . . . ?
C18A C13A C14A C19A 177.34(19) . . . . ?
N2A C13A C14A C19A -0.6(3) . . . . ?
C13A C14A C15A C16A 0.7(3) . . . . ?
C19A C14A C15A C16A 179.5(2) . . . . ?
C14A C15A C16A C17A 2.2(3) . . . . ?
C15A C16A C17A C18A -2.2(3) . . . . ?
C16A C17A C18A C13A -0.8(3) . . . . ?
C16A C17A C18A C22A 174.3(2) . . . . ?
C14A C13A C18A C17A 3.9(3) . . . . ?
N2A C13A C18A C17A -178.15(18) . . . . ?
C14A C13A C18A C22A -171.29(19) . . . . ?
N2A C13A C18A C22A 6.7(3) . . . . ?
C15A C14A C19A C21A 36.4(3) . . . . ?
C13A C14A C19A C21A -144.9(2) . . . . ?
C15A C14A C19A C20A -88.4(3) . . . . ?
C13A C14A C19A C20A 90.4(2) . . . . ?
C17A C18A C22A C23A -90.7(3) . . . . ?
C13A C18A C22A C23A 84.3(2) . . . . ?
C17A C18A C22A C24A 32.6(3) . . . . ?
C13A C18A C22A C24A -152.4(2) . . . . ?
C5B N1B C2B C3B -0.1(2) . . . . ?
C5B N1B C2B C6B 174.96(17) . . . . ?
N1B C2B C3B C4B 0.2(2) . . . . ?
C6B C2B C3B C4B -174.3(2) . . . . ?
C2B C3B C4B C5B -0.3(2) . . . . ?
C2B N1B C5B C4B -0.1(2) . . . . ?
C2B N1B C5B C7B -176.86(17) . . . . ?
C3B C4B C5B N1B 0.2(2) . . . . ?
C3B C4B C5B C7B 176.6(2) . . . . ?
C13B N2B C6B C2B -175.73(17) . . . . ?
N1B C2B C6B N2B 0.6(3) . . . . ?
C3B C2B C6B N2B 174.5(2) . . . . ?
N1B C5B C7B C8B 170.30(19) . . . . ?
C4B C5B C7B C8B -5.6(3) . . . . ?
N1B C5B C7B C12B -7.8(3) . . . . ?
C4B C5B C7B C12B 176.3(2) . . . . ?
C12B C7B C8B C9B 1.8(3) . . . . ?
C5B C7B C8B C9B -176.38(19) . . . . ?
C7B C8B C9B C10B -0.2(3) . . . . ?
C8B C9B C10B C11B -1.3(3) . . . . ?
C9B C10B C11B C12B 1.3(3) . . . . ?
C10B C11B C12B C7B 0.3(3) . . . . ?
C8B C7B C12B C11B -1.8(3) . . . . ?
C5B C7B C12B C11B 176.31(18) . . . . ?
C6B N2B C13B C14B -98.7(2) . . . . ?
C6B N2B C13B C18B 86.4(2) . . . . ?
C18B C13B C14B C15B -2.0(3) . . . . ?
N2B C13B C14B C15B -176.8(2) . . . . ?
C18B C13B C14B C19B 178.2(2) . . . . ?
N2B C13B C14B C19B 3.4(3) . . . . ?
C13B C14B C15B C16B 0.9(4) . . . . ?
C19B C14B C15B C16B -179.3(2) . . . . ?
C14B C15B C16B C17B 0.6(4) . . . . ?
C15B C16B C17B C18B -1.1(4) . . . . ?
C16B C17B C18B C13B 0.0(3) . . . . ?
C16B C17B C18B C22B 177.2(2) . . . . ?
C14B C13B C18B C17B 1.5(3) . . . . ?
N2B C13B C18B C17B 176.32(19) . . . . ?
C14B C13B C18B C22B -175.7(2) . . . . ?
N2B C13B C18B C22B -0.9(3) . . . . ?
C15B C14B C19B C20B -89.3(3) . . . . ?
C13B C14B C19B C20B 90.5(2) . . . . ?
C15B C14B C19B C21B 36.5(3) . . . . ?
C13B C14B C19B C21B -143.7(2) . . . . ?
C17B C18B C22B C24B -95.7(3) . . . . ?
C13B C18B C22B C24B 81.4(3) . . . . ?
C17B C18B C22B C23B 29.7(3) . . . . ?
C13B C18B C22B C23B -153.2(2) . . . . ?

_refine_diff_density_max         0.111
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1853554'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C49 H43 F6 N2 Ni P'
_chemical_formula_sum            'C49 H43 F6 N2 Ni P'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         863.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_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.
;

_cell_length_a                   20.749(4)
_cell_length_b                   11.3247(19)
_cell_length_c                   17.904(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.833(8)
_cell_angle_gamma                90
_cell_volume                     4197.6(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1442
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      21.98
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             1792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.564
_shelx_estimated_absorpt_T_min   0.896
_shelx_estimated_absorpt_T_max   0.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.896
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16545
_diffrn_reflns_av_unetI/netI     0.4006
_diffrn_reflns_av_R_equivalents  0.2995
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.129
_diffrn_reflns_theta_max         25.772
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.949
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.949
_reflns_number_total             7570
_reflns_number_gt                2147
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.

 Crystals of complex 6 were of poor quality and showed a 
 weak diffracting power for resolutions better than 0.82 A. 
 This led to a high Rint (0.299), a relatively low ratio of 
 observed/unique reflections (28%) and final low completeness 
 of 94.9%. Due to the poor quality of the crystal and corresponding
 data, even though all the atoms were correctly assigned and 
 no twinning was found, two larger than expected residual 
 density maxima of 2.09 and 3.03 eA-3 were present close to 
 the metal atom (nickel) location after completion of the 
 structure refinement. All this led to a final high wR2 value
 of 0.3910 and to a low bond precision on C-C bonds of 0.01845 Ang.   
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP and Mercury'
_computing_publication_material  enCIFer
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1676P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7570
_refine_ls_number_parameters     532
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.3232
_refine_ls_R_factor_gt           0.1170
_refine_ls_wR_factor_ref         0.3910
_refine_ls_wR_factor_gt          0.2564
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_restrained_S_all      0.950
_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 0.25210(6) 0.06257(15) 0.77501(8) 0.0219(5) Uani 1 1 d . . . . .
P1 P 0.26191(13) 0.2526(3) 0.77834(16) 0.0239(8) Uani 1 1 d . . . . .
F1 F -0.1004(4) 0.4091(8) 0.8302(5) 0.058(3) Uani 1 1 d . . . . .
F4 F -0.0225(3) 0.2325(8) 0.5922(4) 0.053(2) Uani 1 1 d . . . . .
F5 F 0.0460(4) 0.3755(8) 0.6011(5) 0.059(2) Uani 1 1 d . . . . .
F6 F 0.0786(4) 0.1962(8) 0.5900(4) 0.049(2) Uani 1 1 d . . . . .
N1 N 0.1792(4) 0.0247(8) 0.8373(4) 0.015(2) Uani 1 1 d . . . . .
N2 N 0.2754(4) -0.1013(9) 0.7987(5) 0.021(2) Uani 1 1 d . U . . .
C2 C 0.1907(5) -0.0734(12) 0.8759(6) 0.027(3) Uani 1 1 d . . . . .
C3 C 0.1441(6) -0.0917(12) 0.9283(7) 0.036(4) Uani 1 1 d . . . . .
H3 H 0.142876 -0.153366 0.964190 0.043 Uiso 1 1 calc R U . . .
C4 C 0.1019(6) -0.0036(13) 0.9167(6) 0.031(3) Uani 1 1 d . . . . .
H4 H 0.064255 0.008254 0.943239 0.037 Uiso 1 1 calc R U . . .
C5 C 0.1225(5) 0.0708(12) 0.8572(6) 0.030(3) Uani 1 1 d . . . . .
C6 C 0.2459(5) -0.1410(11) 0.8539(7) 0.027(3) Uani 1 1 d . . . . .
H6 H 0.259362 -0.211367 0.879319 0.032 Uiso 1 1 calc R U . . .
C7 C 0.0833(5) 0.1602(11) 0.8198(6) 0.027(3) Uani 1 1 d . . . . .
C8 C 0.0400(6) 0.2297(12) 0.8588(7) 0.034(3) Uani 1 1 d . . . . .
H8 H 0.041747 0.226013 0.911908 0.041 Uiso 1 1 calc R U . . .
C9 C -0.0035(6) 0.3005(14) 0.8230(7) 0.040(4) Uani 1 1 d . . . . .
C10 C -0.0042(6) 0.3139(13) 0.7450(8) 0.044(4) Uani 1 1 d . . . . .
H10 H -0.033787 0.366333 0.719404 0.052 Uiso 1 1 calc R U . . .
C11 C 0.0384(5) 0.2504(12) 0.7067(6) 0.033(3) Uani 1 1 d . . . . .
C12 C 0.0821(5) 0.1766(13) 0.7416(7) 0.034(3) Uani 1 1 d . . . . .
H12 H 0.112206 0.135789 0.713311 0.041 Uiso 1 1 calc R U . . .
C14 C 0.0349(6) 0.2609(13) 0.6231(7) 0.035(3) Uani 1 1 d . U . . .
C15 C 0.3271(6) -0.1759(11) 0.7711(7) 0.030(3) Uani 1 1 d . U . . .
C16 C 0.3129(7) -0.2282(13) 0.7032(7) 0.041(4) Uani 1 1 d . . . . .
C17 C 0.3616(8) -0.2954(15) 0.6738(9) 0.052(4) Uani 1 1 d . . . . .
H17 H 0.351742 -0.336640 0.628252 0.063 Uiso 1 1 calc R U . . .
C18 C 0.4207(8) -0.3050(15) 0.7058(9) 0.059(5) Uani 1 1 d . . . . .
H18 H 0.453672 -0.344387 0.681167 0.070 Uiso 1 1 calc R U . . .
C19 C 0.4338(7) -0.2543(13) 0.7791(8) 0.047(4) Uani 1 1 d . . . . .
H19 H 0.474671 -0.265374 0.805288 0.056 Uiso 1 1 calc R U . . .
C20 C 0.3856(6) -0.1883(12) 0.8117(6) 0.029(3) Uani 1 1 d . . . . .
C21 C 0.2481(7) -0.2203(12) 0.6615(7) 0.035(3) Uani 1 1 d . . . . .
H21 H 0.228593 -0.143305 0.675445 0.042 Uiso 1 1 calc R U . . .
C22 C 0.4027(8) -0.1351(14) 0.8889(7) 0.052(5) Uani 1 1 d . . . . .
H22 H 0.370399 -0.071834 0.897689 0.062 Uiso 1 1 calc R U . . .
C23 C 0.2491(8) -0.2221(13) 0.5756(6) 0.045(4) Uani 1 1 d . . . . .
H23A H 0.204791 -0.216639 0.553203 0.067 Uiso 1 1 calc R U . . .
H23B H 0.274338 -0.154948 0.559146 0.067 Uiso 1 1 calc R U . . .
H23C H 0.268779 -0.295885 0.559806 0.067 Uiso 1 1 calc R U . . .
C24 C 0.2059(9) -0.3166(14) 0.6900(9) 0.061(5) Uani 1 1 d . . . . .
H24A H 0.163123 -0.313052 0.663340 0.091 Uiso 1 1 calc R U . . .
H24B H 0.225583 -0.393681 0.681317 0.091 Uiso 1 1 calc R U . . .
H24C H 0.201609 -0.305742 0.743701 0.091 Uiso 1 1 calc R U . . .
C25 C 0.4683(7) -0.0805(16) 0.8960(9) 0.068(5) Uani 1 1 d . . . . .
H25A H 0.476420 -0.048051 0.946470 0.102 Uiso 1 1 calc R U . . .
H25B H 0.500837 -0.140594 0.886995 0.102 Uiso 1 1 calc R U . . .
H25C H 0.470623 -0.016962 0.859087 0.102 Uiso 1 1 calc R U . . .
C26 C 0.3963(10) -0.2310(17) 0.9488(9) 0.077(6) Uani 1 1 d . . . . .
H26A H 0.352986 -0.265721 0.943265 0.115 Uiso 1 1 calc R U . . .
H26B H 0.428660 -0.292699 0.942651 0.115 Uiso 1 1 calc R U . . .
H26C H 0.403230 -0.195788 0.998709 0.115 Uiso 1 1 calc R U . . .
C27 C 0.3146(6) 0.0725(13) 0.7026(6) 0.035(3) Uani 1 1 d . . . . .
C28 C 0.2861(7) 0.0723(11) 0.6294(7) 0.037(4) Uani 1 1 d . . . . .
H28 H 0.240608 0.078683 0.620414 0.045 Uiso 1 1 calc R U . . .
C29 C 0.3271(8) 0.0622(13) 0.5680(8) 0.049(4) Uani 1 1 d . . . . .
H29 H 0.309271 0.060344 0.517777 0.059 Uiso 1 1 calc R U . . .
C30 C 0.3937(7) 0.0552(13) 0.5841(9) 0.048(4) Uani 1 1 d . . . . .
H30 H 0.421259 0.051458 0.543875 0.057 Uiso 1 1 calc R U . . .
C31 C 0.4204(6) 0.0537(13) 0.6553(8) 0.045(4) Uani 1 1 d . . . . .
H31 H 0.465803 0.045321 0.664877 0.054 Uiso 1 1 calc R U . . .
C32 C 0.3800(6) 0.0647(11) 0.7145(7) 0.028(3) Uani 1 1 d . . . . .
H32 H 0.398674 0.066744 0.764356 0.034 Uiso 1 1 calc R U . . .
C33 C 0.2669(7) 0.3285(11) 0.6885(7) 0.034(3) Uani 1 1 d . . . . .
C34 C 0.2098(6) 0.3468(11) 0.6450(6) 0.031(3) Uani 1 1 d . . . . .
H34 H 0.169397 0.328396 0.664256 0.037 Uiso 1 1 calc R U . . .
C35 C 0.2123(7) 0.3929(12) 0.5721(7) 0.040(4) Uani 1 1 d . U . . .
H35 H 0.173832 0.403788 0.541052 0.048 Uiso 1 1 calc R U . . .
C36 C 0.2701(7) 0.4213(12) 0.5472(7) 0.038(3) Uani 1 1 d . U . . .
H36 H 0.271416 0.455652 0.498884 0.045 Uiso 1 1 calc R U . . .
C37 C 0.3266(7) 0.4029(12) 0.5883(7) 0.041(4) Uani 1 1 d . U . . .
H37 H 0.366630 0.421223 0.568221 0.050 Uiso 1 1 calc R U . . .
C38 C 0.3251(7) 0.3563(12) 0.6611(7) 0.037(3) Uani 1 1 d . . . . .
H38 H 0.364093 0.344291 0.690921 0.044 Uiso 1 1 calc R U . . .
C39 C 0.3375(5) 0.2892(11) 0.8296(6) 0.026(3) Uani 1 1 d . U . . .
C40 C 0.3592(6) 0.4113(12) 0.8308(7) 0.037(3) Uani 1 1 d . . . . .
H40 H 0.334625 0.471801 0.805495 0.044 Uiso 1 1 calc R U . . .
C41 C 0.4178(6) 0.4356(15) 0.8707(7) 0.043(4) Uani 1 1 d . . . . .
H41 H 0.433762 0.514114 0.869481 0.051 Uiso 1 1 calc R U . . .
C42 C 0.4534(6) 0.3550(15) 0.9112(8) 0.050(4) Uani 1 1 d . . . . .
H42 H 0.492537 0.376397 0.938360 0.060 Uiso 1 1 calc R U . . .
C43 C 0.4306(6) 0.2398(15) 0.9113(8) 0.053(5) Uani 1 1 d . . . . .
H43 H 0.455917 0.179394 0.935545 0.063 Uiso 1 1 calc R U . . .
C44 C 0.3704(6) 0.2128(14) 0.8759(7) 0.041(4) Uani 1 1 d . . . . .
H44 H 0.351798 0.137764 0.884745 0.049 Uiso 1 1 calc R U . . .
C45 C 0.2085(5) 0.3378(11) 0.8332(6) 0.023(3) Uani 1 1 d . . . . .
C46 C 0.2053(6) 0.3099(12) 0.9066(6) 0.030(3) Uani 1 1 d . . . . .
H46 H 0.229269 0.243734 0.925619 0.036 Uiso 1 1 calc R U . . .
C47 C 0.1691(6) 0.3724(12) 0.9554(6) 0.029(3) Uani 1 1 d . U . . .
H47 H 0.167193 0.347156 1.005813 0.035 Uiso 1 1 calc R U . . .
C48 C 0.1364(7) 0.4698(14) 0.9308(8) 0.047(4) Uani 1 1 d . . . . .
H48 H 0.113155 0.515629 0.964374 0.056 Uiso 1 1 calc R U . . .
C49 C 0.1370(9) 0.5027(14) 0.8549(9) 0.056(4) Uani 1 1 d . . . . .
H49 H 0.112785 0.568925 0.836445 0.067 Uiso 1 1 calc R U . . .
C50 C 0.1737(6) 0.4370(12) 0.8070(7) 0.036(3) Uani 1 1 d . U . . .
H50 H 0.175068 0.460032 0.756134 0.043 Uiso 1 1 calc R U . . .
F2 F -0.0676(5) 0.3130(11) 0.9269(6) 0.094(4) Uani 1 1 d . . . . .
C13 C -0.0477(7) 0.3723(16) 0.8654(8) 0.047(4) Uani 1 1 d . . . . .
F3 F -0.0184(5) 0.4713(11) 0.8931(7) 0.103(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 C27 1.897(12) . ?
Ni1 N2 1.956(10) . ?
Ni1 N1 1.985(9) . ?
Ni1 P1 2.162(4) . ?
P1 C39 1.811(11) . ?
P1 C45 1.808(13) . ?
P1 C33 1.833(13) . ?
F1 C13 1.294(15) . ?
F4 C14 1.321(14) . ?
F5 C14 1.379(16) . ?
F6 C14 1.335(15) . ?
N1 C2 1.321(15) . ?
N1 C5 1.358(14) . ?
N2 C6 1.279(15) . ?
N2 C15 1.478(15) . ?
C2 C3 1.408(16) . ?
C2 C6 1.454(16) . ?
C3 C4 1.334(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.445(17) . ?
C4 H4 0.9500 . ?
C5 C7 1.436(16) . ?
C6 H6 0.9500 . ?
C7 C12 1.410(17) . ?
C7 C8 1.414(17) . ?
C8 C9 1.338(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.404(19) . ?
C9 C13 1.47(2) . ?
C10 C11 1.360(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.355(17) . ?
C11 C14 1.498(17) . ?
C12 H12 0.9500 . ?
C15 C16 1.366(17) . ?
C15 C20 1.380(15) . ?
C16 C17 1.40(2) . ?
C16 C21 1.496(18) . ?
C17 C18 1.32(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.44(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.405(18) . ?
C19 H19 0.9500 . ?
C20 C22 1.529(17) . ?
C21 C24 1.508(19) . ?
C21 C23 1.540(17) . ?
C21 H21 1.0000 . ?
C22 C25 1.49(2) . ?
C22 C26 1.54(2) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C32 1.362(17) . ?
C27 C28 1.402(15) . ?
C28 C29 1.44(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.40(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.355(19) . ?
C30 H30 0.9500 . ?
C31 C32 1.401(17) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C38 1.369(19) . ?
C33 C34 1.389(17) . ?
C34 C35 1.411(18) . ?
C34 H34 0.9500 . ?
C35 C36 1.346(19) . ?
C35 H35 0.9500 . ?
C36 C37 1.358(18) . ?
C36 H36 0.9500 . ?
C37 C38 1.408(18) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 C44 1.352(16) . ?
C39 C40 1.454(18) . ?
C40 C41 1.396(16) . ?
C40 H40 0.9500 . ?
C41 C42 1.35(2) . ?
C41 H41 0.9500 . ?
C42 C43 1.39(2) . ?
C42 H42 0.9500 . ?
C43 C44 1.397(17) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
C45 C46 1.359(16) . ?
C45 C50 1.398(17) . ?
C46 C47 1.384(17) . ?
C46 H46 0.9500 . ?
C47 C48 1.353(19) . ?
C47 H47 0.9500 . ?
C48 C49 1.41(2) . ?
C48 H48 0.9500 . ?
C49 C50 1.398(19) . ?
C49 H49 0.9500 . ?
C50 H50 0.9500 . ?
F2 C13 1.378(18) . ?
C13 F3 1.354(18) . ?

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
C27 Ni1 N2 92.0(5) . . ?
C27 Ni1 N1 167.9(5) . . ?
N2 Ni1 N1 81.9(4) . . ?
C27 Ni1 P1 83.8(5) . . ?
N2 Ni1 P1 156.4(3) . . ?
N1 Ni1 P1 105.9(3) . . ?
C39 P1 C45 98.3(5) . . ?
C39 P1 C33 103.8(6) . . ?
C45 P1 C33 107.4(6) . . ?
C39 P1 Ni1 108.6(4) . . ?
C45 P1 Ni1 119.1(4) . . ?
C33 P1 Ni1 117.0(4) . . ?
C2 N1 C5 108.3(10) . . ?
C2 N1 Ni1 111.0(7) . . ?
C5 N1 Ni1 140.5(9) . . ?
C6 N2 C15 116.9(10) . . ?
C6 N2 Ni1 112.2(8) . . ?
C15 N2 Ni1 130.1(8) . . ?
N1 C2 C3 111.4(11) . . ?
N1 C2 C6 114.7(11) . . ?
C3 C2 C6 133.8(13) . . ?
C4 C3 C2 105.0(11) . . ?
C4 C3 H3 127.5 . . ?
C2 C3 H3 127.5 . . ?
C3 C4 C5 109.1(12) . . ?
C3 C4 H4 125.4 . . ?
C5 C4 H4 125.4 . . ?
N1 C5 C7 128.5(11) . . ?
N1 C5 C4 105.9(11) . . ?
C7 C5 C4 124.7(11) . . ?
N2 C6 C2 116.7(11) . . ?
N2 C6 H6 121.6 . . ?
C2 C6 H6 121.6 . . ?
C12 C7 C8 116.6(11) . . ?
C12 C7 C5 121.8(12) . . ?
C8 C7 C5 121.4(11) . . ?
C9 C8 C7 121.8(13) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 120.2(13) . . ?
C8 C9 C13 120.4(12) . . ?
C10 C9 C13 119.2(12) . . ?
C11 C10 C9 118.7(12) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C12 C11 C10 122.1(11) . . ?
C12 C11 C14 119.8(12) . . ?
C10 C11 C14 118.1(12) . . ?
C11 C12 C7 120.4(12) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
F4 C14 F6 107.5(11) . . ?
F4 C14 F5 105.8(10) . . ?
F6 C14 F5 105.1(11) . . ?
F4 C14 C11 112.4(11) . . ?
F6 C14 C11 114.2(10) . . ?
F5 C14 C11 111.3(11) . . ?
C16 C15 C20 123.7(13) . . ?
C16 C15 N2 115.3(11) . . ?
C20 C15 N2 121.0(11) . . ?
C15 C16 C17 117.0(13) . . ?
C15 C16 C21 123.4(13) . . ?
C17 C16 C21 119.6(13) . . ?
C18 C17 C16 123.7(15) . . ?
C18 C17 H17 118.2 . . ?
C16 C17 H17 118.2 . . ?
C17 C18 C19 118.3(15) . . ?
C17 C18 H18 120.8 . . ?
C19 C18 H18 120.8 . . ?
C20 C19 C18 119.6(13) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C15 C20 C19 117.4(12) . . ?
C15 C20 C22 125.4(12) . . ?
C19 C20 C22 117.2(11) . . ?
C16 C21 C24 108.2(12) . . ?
C16 C21 C23 115.2(13) . . ?
C24 C21 C23 112.0(11) . . ?
C16 C21 H21 107.0 . . ?
C24 C21 H21 107.0 . . ?
C23 C21 H21 107.0 . . ?
C25 C22 C20 113.3(14) . . ?
C25 C22 C26 110.7(12) . . ?
C20 C22 C26 109.1(13) . . ?
C25 C22 H22 107.9 . . ?
C20 C22 H22 107.9 . . ?
C26 C22 H22 107.9 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C26 H26A 109.5 . . ?
C22 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C22 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C32 C27 C28 119.9(12) . . ?
C32 C27 Ni1 127.5(9) . . ?
C28 C27 Ni1 112.0(10) . . ?
C27 C28 C29 118.7(13) . . ?
C27 C28 H28 120.6 . . ?
C29 C28 H28 120.6 . . ?
C30 C29 C28 118.4(14) . . ?
C30 C29 H29 120.8 . . ?
C28 C29 H29 120.8 . . ?
C31 C30 C29 122.2(14) . . ?
C31 C30 H30 118.9 . . ?
C29 C30 H30 118.9 . . ?
C30 C31 C32 118.8(12) . . ?
C30 C31 H31 120.6 . . ?
C32 C31 H31 120.6 . . ?
C27 C32 C31 121.9(11) . . ?
C27 C32 H32 119.0 . . ?
C31 C32 H32 119.0 . . ?
C38 C33 C34 120.3(12) . . ?
C38 C33 P1 121.7(10) . . ?
C34 C33 P1 117.7(11) . . ?
C33 C34 C35 119.4(13) . . ?
C33 C34 H34 120.3 . . ?
C35 C34 H34 120.3 . . ?
C36 C35 C34 119.0(12) . . ?
C36 C35 H35 120.5 . . ?
C34 C35 H35 120.5 . . ?
C35 C36 C37 122.6(13) . . ?
C35 C36 H36 118.7 . . ?
C37 C36 H36 118.7 . . ?
C36 C37 C38 119.2(14) . . ?
C36 C37 H37 120.4 . . ?
C38 C37 H37 120.4 . . ?
C33 C38 C37 119.5(13) . . ?
C33 C38 H38 120.2 . . ?
C37 C38 H38 120.2 . . ?
C44 C39 C40 117.2(11) . . ?
C44 C39 P1 123.3(10) . . ?
C40 C39 P1 118.8(9) . . ?
C41 C40 C39 116.9(12) . . ?
C41 C40 H40 121.5 . . ?
C39 C40 H40 121.5 . . ?
C42 C41 C40 124.5(15) . . ?
C42 C41 H41 117.7 . . ?
C40 C41 H41 117.7 . . ?
C41 C42 C43 117.4(12) . . ?
C41 C42 H42 121.3 . . ?
C43 C42 H42 121.3 . . ?
C44 C43 C42 120.0(13) . . ?
C44 C43 H43 120.0 . . ?
C42 C43 H43 120.0 . . ?
C39 C44 C43 122.5(14) . . ?
C39 C44 H44 118.8 . . ?
C43 C44 H44 118.8 . . ?
C46 C45 C50 116.9(12) . . ?
C46 C45 P1 118.2(9) . . ?
C50 C45 P1 124.6(9) . . ?
C45 C46 C47 123.8(12) . . ?
C45 C46 H46 118.1 . . ?
C47 C46 H46 118.1 . . ?
C48 C47 C46 119.5(12) . . ?
C48 C47 H47 120.2 . . ?
C46 C47 H47 120.2 . . ?
C47 C48 C49 119.5(13) . . ?
C47 C48 H48 120.2 . . ?
C49 C48 H48 120.2 . . ?
C50 C49 C48 119.4(14) . . ?
C50 C49 H49 120.3 . . ?
C48 C49 H49 120.3 . . ?
C45 C50 C49 120.8(12) . . ?
C45 C50 H50 119.6 . . ?
C49 C50 H50 119.6 . . ?
F1 C13 F3 104.8(14) . . ?
F1 C13 F2 104.8(12) . . ?
F3 C13 F2 105.1(12) . . ?
F1 C13 C9 117.5(11) . . ?
F3 C13 C9 111.6(12) . . ?
F2 C13 C9 112.0(14) . . ?

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
C5 N1 C2 C3 -4.9(12) . . . . ?
Ni1 N1 C2 C3 171.2(7) . . . . ?
C5 N1 C2 C6 172.7(9) . . . . ?
Ni1 N1 C2 C6 -11.2(11) . . . . ?
N1 C2 C3 C4 3.4(12) . . . . ?
C6 C2 C3 C4 -173.6(12) . . . . ?
C2 C3 C4 C5 -0.6(13) . . . . ?
C2 N1 C5 C7 -164.9(12) . . . . ?
Ni1 N1 C5 C7 20.8(19) . . . . ?
C2 N1 C5 C4 4.3(11) . . . . ?
Ni1 N1 C5 C4 -170.0(8) . . . . ?
C3 C4 C5 N1 -2.2(13) . . . . ?
C3 C4 C5 C7 167.5(11) . . . . ?
C15 N2 C6 C2 -173.8(9) . . . . ?
Ni1 N2 C6 C2 15.1(13) . . . . ?
N1 C2 C6 N2 -2.5(15) . . . . ?
C3 C2 C6 N2 174.4(11) . . . . ?
N1 C5 C7 C12 29.0(19) . . . . ?
C4 C5 C7 C12 -138.3(12) . . . . ?
N1 C5 C7 C8 -156.2(12) . . . . ?
C4 C5 C7 C8 36.5(18) . . . . ?
C12 C7 C8 C9 5.2(19) . . . . ?
C5 C7 C8 C9 -169.9(13) . . . . ?
C7 C8 C9 C10 -4(2) . . . . ?
C7 C8 C9 C13 -179.6(13) . . . . ?
C8 C9 C10 C11 2(2) . . . . ?
C13 C9 C10 C11 177.6(13) . . . . ?
C9 C10 C11 C12 -1(2) . . . . ?
C9 C10 C11 C14 177.0(13) . . . . ?
C10 C11 C12 C7 2(2) . . . . ?
C14 C11 C12 C7 -176.0(12) . . . . ?
C8 C7 C12 C11 -4.0(18) . . . . ?
C5 C7 C12 C11 171.0(11) . . . . ?
C12 C11 C14 F4 120.9(13) . . . . ?
C10 C11 C14 F4 -57.5(18) . . . . ?
C12 C11 C14 F6 -1.9(19) . . . . ?
C10 C11 C14 F6 179.7(12) . . . . ?
C12 C11 C14 F5 -120.7(13) . . . . ?
C10 C11 C14 F5 61.0(16) . . . . ?
C6 N2 C15 C16 108.5(14) . . . . ?
Ni1 N2 C15 C16 -82.2(14) . . . . ?
C6 N2 C15 C20 -72.8(16) . . . . ?
Ni1 N2 C15 C20 96.5(14) . . . . ?
C20 C15 C16 C17 -1(2) . . . . ?
N2 C15 C16 C17 177.4(13) . . . . ?
C20 C15 C16 C21 176.2(13) . . . . ?
N2 C15 C16 C21 -5(2) . . . . ?
C15 C16 C17 C18 -4(3) . . . . ?
C21 C16 C17 C18 178.3(16) . . . . ?
C16 C17 C18 C19 7(3) . . . . ?
C17 C18 C19 C20 -5(3) . . . . ?
C16 C15 C20 C19 3(2) . . . . ?
N2 C15 C20 C19 -175.8(12) . . . . ?
C16 C15 C20 C22 -177.7(14) . . . . ?
N2 C15 C20 C22 4(2) . . . . ?
C18 C19 C20 C15 0(2) . . . . ?
C18 C19 C20 C22 -179.1(14) . . . . ?
C15 C16 C21 C24 -85.4(17) . . . . ?
C17 C16 C21 C24 92.1(17) . . . . ?
C15 C16 C21 C23 148.5(14) . . . . ?
C17 C16 C21 C23 -34.1(19) . . . . ?
C15 C20 C22 C25 -136.0(15) . . . . ?
C19 C20 C22 C25 43.3(19) . . . . ?
C15 C20 C22 C26 100.2(17) . . . . ?
C19 C20 C22 C26 -80.5(17) . . . . ?
N2 Ni1 C27 C32 -64.2(14) . . . . ?
N1 Ni1 C27 C32 -123(2) . . . . ?
P1 Ni1 C27 C32 92.5(14) . . . . ?
N2 Ni1 C27 C28 107.0(10) . . . . ?
N1 Ni1 C27 C28 48(3) . . . . ?
P1 Ni1 C27 C28 -96.3(10) . . . . ?
C32 C27 C28 C29 1(2) . . . . ?
Ni1 C27 C28 C29 -171.2(10) . . . . ?
C27 C28 C29 C30 -1(2) . . . . ?
C28 C29 C30 C31 2(2) . . . . ?
C29 C30 C31 C32 -3(2) . . . . ?
C28 C27 C32 C31 -1(2) . . . . ?
Ni1 C27 C32 C31 169.2(11) . . . . ?
C30 C31 C32 C27 2(2) . . . . ?
C39 P1 C33 C38 24.7(13) . . . . ?
C45 P1 C33 C38 128.2(11) . . . . ?
Ni1 P1 C33 C38 -94.9(12) . . . . ?
C39 P1 C33 C34 -161.6(10) . . . . ?
C45 P1 C33 C34 -58.2(11) . . . . ?
Ni1 P1 C33 C34 78.8(11) . . . . ?
C38 C33 C34 C35 1(2) . . . . ?
P1 C33 C34 C35 -173.0(9) . . . . ?
C33 C34 C35 C36 -2(2) . . . . ?
C34 C35 C36 C37 3(2) . . . . ?
C35 C36 C37 C38 -2(2) . . . . ?
C34 C33 C38 C37 0(2) . . . . ?
P1 C33 C38 C37 173.1(10) . . . . ?
C36 C37 C38 C33 1(2) . . . . ?
C45 P1 C39 C44 106.3(12) . . . . ?
C33 P1 C39 C44 -143.4(11) . . . . ?
Ni1 P1 C39 C44 -18.3(12) . . . . ?
C45 P1 C39 C40 -63.6(10) . . . . ?
C33 P1 C39 C40 46.6(11) . . . . ?
Ni1 P1 C39 C40 171.8(8) . . . . ?
C44 C39 C40 C41 9.6(18) . . . . ?
P1 C39 C40 C41 -179.8(10) . . . . ?
C39 C40 C41 C42 -4(2) . . . . ?
C40 C41 C42 C43 1(2) . . . . ?
C41 C42 C43 C44 -5(2) . . . . ?
C40 C39 C44 C43 -14(2) . . . . ?
P1 C39 C44 C43 175.9(11) . . . . ?
C42 C43 C44 C39 12(2) . . . . ?
C39 P1 C45 C46 -62.1(10) . . . . ?
C33 P1 C45 C46 -169.5(9) . . . . ?
Ni1 P1 C45 C46 54.7(10) . . . . ?
C39 P1 C45 C50 112.6(11) . . . . ?
C33 P1 C45 C50 5.3(12) . . . . ?
Ni1 P1 C45 C50 -130.6(10) . . . . ?
C50 C45 C46 C47 1.2(18) . . . . ?
P1 C45 C46 C47 176.3(10) . . . . ?
C45 C46 C47 C48 -2.5(19) . . . . ?
C46 C47 C48 C49 3(2) . . . . ?
C47 C48 C49 C50 -3(2) . . . . ?
C46 C45 C50 C49 -0.7(19) . . . . ?
P1 C45 C50 C49 -175.4(12) . . . . ?
C48 C49 C50 C45 1(2) . . . . ?
C8 C9 C13 F1 -158.8(14) . . . . ?
C10 C9 C13 F1 26(2) . . . . ?
C8 C9 C13 F3 80.2(19) . . . . ?
C10 C9 C13 F3 -95.0(16) . . . . ?
C8 C9 C13 F2 -37.3(19) . . . . ?
C10 C9 C13 F2 147.5(14) . . . . ?

_refine_diff_density_max         3.031
_refine_diff_density_min         -2.537
_refine_diff_density_rms         0.258

####################################################################### 
# 
# 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_IA
_database_code_depnum_ccdc_archive 'CCDC 1853542'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_IA                  
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.931 Why?
RESPONSE: The crystal of compound IA was of poor quality (Rint=0.1789) and showed a weak diffracting power for resolutions better than 0.82 \%A, which led to a final low completeness of only 93.1%.
;
_vrf_PLAT026_IA                  
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        37% Check
RESPONSE: Due to the weak diffracting power and poor quality of the crystal of IA, the ratio between observed and unique reflections is low (37%).
;
_vrf_PLAT049_IA                  
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 .........     0.9890 Check
RESPONSE: Due to the weak diffracting power and poor quality of the crystal of IA, the final density obtained is 0.9890. However, the model is not incomplete nor the crystal solved in an incorrect symmetry.
;
_vrf_PLAT149_IA                  
;
PROBLEM: s.u. on the   beta    Angle is Too Large .......       0.07 Degree
RESPONSE: Due to the weak diffracting power and poor quality of the crystal of IA, the bond precision is low (0.0075 \%A) and, consequently, the s.u. associated to the bond angle beta is large (0.07 ?).
;
_vrf_PLAT369_IA                  
;
PROBLEM: Long   C(sp2)-C(sp2) Bond  C5       - C7       .       1.63 Ang.
RESPONSE: This crystal is of poor quality, which leads to model problems, such as the long bond length in a conjugated system.
;
_vrf_PLAT911_IA                  
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.595        319 Report
RESPONSE: This crystal is of poor quality, which leads to problems such as the inexistence of a large amount of reflections (319) between Thmin & STh/L. Nevertheless, this does not affects the final solution and convergence of the final structure.
;
# Added during the CSD deposition process: Wednesday 05 September 2018 04:18 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H18 N2, C8 H11 N'
_chemical_formula_sum            'C27 H29 N3'
_chemical_melting_point          ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         395.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_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.
;

_cell_length_a                   13.74(2)
_cell_length_b                   8.779(15)
_cell_length_c                   22.72(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.18(7)
_cell_angle_gamma                90
_cell_volume                     2658(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    971
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      17.73
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.988
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.058
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19434
_diffrn_reflns_av_unetI/netI     0.1712
_diffrn_reflns_av_R_equivalents  0.1789
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.808
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.931
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.931
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.931
_reflns_number_total             4378
_reflns_number_gt                1610
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.

 Crystals of ligand precursor IA were of poor quality 
 and showed a weak diffracting power for resolutions better
 than 0.82 A. This led to a relatively low ratio of observed/
 unique reflections (37%) and final low completeness of 93.1%.
 Due to the poor quality of the crystal and corresponding
 data, a low density of 0.9890 gcm-3, a bond precision of
 0.0075 Ang, a large s.u. on the beta angle (0.07), the inexistence
 of a large amount of reflections (319) between Thmin & STh/L,
 and a long bond length in a conjugated system were observed.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1422P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4378
_refine_ls_number_parameters     276
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2302
_refine_ls_R_factor_gt           0.0877
_refine_ls_wR_factor_ref         0.2684
_refine_ls_wR_factor_gt          0.2178
_refine_ls_goodness_of_fit_ref   0.866
_refine_ls_restrained_S_all      0.867
_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
N1 N -0.0482(3) 0.4530(5) 0.32534(18) 0.0418(11) Uani 1 1 d . . . . .
N2 N 0.1585(3) 0.2863(5) 0.35597(19) 0.0510(12) Uani 1 1 d . . . . .
C2 C 0.0409(4) 0.4995(6) 0.3065(2) 0.0429(13) Uani 1 1 d . . . . .
C3 C 0.0161(4) 0.6387(6) 0.2719(2) 0.0478(14) Uani 1 1 d . . . . .
H3 H 0.059865 0.695286 0.253691 0.057 Uiso 1 1 calc R U . . .
C4 C -0.0886(4) 0.6770(6) 0.2699(2) 0.0512(15) Uani 1 1 d . . . . .
H4 H -0.124359 0.763135 0.250371 0.061 Uiso 1 1 calc R U . . .
C5 C -0.1286(4) 0.5582(5) 0.3035(2) 0.0433(13) Uani 1 1 d . . . . .
C6 C 0.1394(4) 0.4180(6) 0.3237(2) 0.0511(15) Uani 1 1 d . . . . .
H6 H 0.193784 0.462471 0.310819 0.061 Uiso 1 1 calc R U . . .
C7 C -0.2398(2) 0.5414(4) 0.31672(15) 0.0398(13) Uani 1 1 d G . . . .
C8 C -0.3182(3) 0.6309(4) 0.28420(13) 0.0525(15) Uani 1 1 d G . . . .
H8 H -0.307087 0.699291 0.254109 0.063 Uiso 1 1 calc R U . . .
C9 C -0.4127(2) 0.6202(4) 0.29570(16) 0.0611(16) Uani 1 1 d G . . . .
H9 H -0.466261 0.681391 0.273478 0.073 Uiso 1 1 calc R U . . .
C10 C -0.4289(2) 0.5201(4) 0.33973(17) 0.0619(16) Uani 1 1 d G . . . .
H10 H -0.493572 0.512856 0.347591 0.074 Uiso 1 1 calc R U . . .
C11 C -0.3506(3) 0.4306(4) 0.37225(14) 0.0502(14) Uani 1 1 d G . . . .
H11 H -0.361708 0.362220 0.402335 0.060 Uiso 1 1 calc R U . . .
C12 C -0.2561(2) 0.4413(3) 0.36074(14) 0.0450(13) Uani 1 1 d G . . . .
H12 H -0.202533 0.380118 0.382967 0.054 Uiso 1 1 calc R U . . .
C13 C 0.2622(4) 0.2188(6) 0.3727(2) 0.0469(14) Uani 1 1 d . . . . .
C14 C 0.3420(4) 0.2875(7) 0.4202(3) 0.0577(16) Uani 1 1 d . . . . .
C15 C 0.4377(5) 0.2056(8) 0.4378(3) 0.0703(18) Uani 1 1 d . . . . .
H15 H 0.489811 0.245966 0.469451 0.084 Uiso 1 1 calc R U . . .
C16 C 0.4555(5) 0.0641(8) 0.4084(3) 0.0727(19) Uani 1 1 d . . . . .
H16 H 0.518819 0.014684 0.420156 0.087 Uiso 1 1 calc R U . . .
C17 C 0.3758(4) -0.0003(7) 0.3612(3) 0.0613(16) Uani 1 1 d . . . . .
H17 H 0.387190 -0.092898 0.342357 0.074 Uiso 1 1 calc R U . . .
C18 C 0.2777(4) 0.0746(6) 0.3419(2) 0.0480(14) Uani 1 1 d . . . . .
C19 C 0.3273(4) 0.4410(7) 0.4537(3) 0.082(2) Uani 1 1 d . . . . .
H19A H 0.381574 0.451791 0.490600 0.123 Uiso 1 1 calc R U . . .
H19B H 0.262629 0.438660 0.464614 0.123 Uiso 1 1 calc R U . . .
H19C H 0.328761 0.527557 0.426697 0.123 Uiso 1 1 calc R U . . .
C20 C 0.1898(4) 0.0048(6) 0.2906(2) 0.0611(16) Uani 1 1 d . . . . .
H20A H 0.129310 -0.004891 0.305975 0.092 Uiso 1 1 calc R U . . .
H20B H 0.209666 -0.095962 0.279127 0.092 Uiso 1 1 calc R U . . .
H20C H 0.175812 0.071874 0.255097 0.092 Uiso 1 1 calc R U . . .
N3 N -0.0435(4) 0.1358(5) 0.39306(19) 0.0469(12) Uani 1 1 d D . . . .
C21 C -0.0836(4) 0.1403(5) 0.4484(2) 0.0379(13) Uani 1 1 d . . . . .
C22 C -0.1787(4) 0.0625(5) 0.4482(2) 0.0425(13) Uani 1 1 d . . . . .
C23 C -0.2209(4) 0.0803(6) 0.5012(2) 0.0511(15) Uani 1 1 d . . . . .
H23 H -0.282449 0.031550 0.501491 0.061 Uiso 1 1 calc R U . . .
C24 C -0.1703(4) 0.1713(6) 0.5533(2) 0.0525(15) Uani 1 1 d . . . . .
H24 H -0.199190 0.182325 0.587054 0.063 Uiso 1 1 calc R U . . .
C25 C -0.0750(4) 0.2455(6) 0.5536(2) 0.0491(14) Uani 1 1 d . . . . .
H25 H -0.041375 0.302819 0.588126 0.059 Uiso 1 1 calc R U . . .
C26 C -0.0302(4) 0.2326(5) 0.5010(2) 0.0439(13) Uani 1 1 d . . . . .
C27 C -0.2344(4) -0.0354(6) 0.3918(2) 0.0593(16) Uani 1 1 d . . . . .
H27A H -0.292631 -0.085829 0.400894 0.089 Uiso 1 1 calc R U . . .
H27B H -0.188324 -0.112511 0.382990 0.089 Uiso 1 1 calc R U . . .
H27C H -0.256786 0.031123 0.356437 0.089 Uiso 1 1 calc R U . . .
C28 C 0.0715(4) 0.3172(6) 0.5005(2) 0.0529(15) Uani 1 1 d . . . . .
H28A H 0.121055 0.242528 0.494282 0.079 Uiso 1 1 calc R U . . .
H28B H 0.097019 0.369167 0.539381 0.079 Uiso 1 1 calc R U . . .
H28C H 0.059264 0.392052 0.467512 0.079 Uiso 1 1 calc R U . . .
H1 H -0.047(4) 0.362(7) 0.339(3) 0.09(2) Uiso 1 1 d . . . . .
H1N H -0.073(3) 0.062(4) 0.3680(16) 0.040(14) Uiso 1 1 d D . . . .
H2N H 0.028(4) 0.159(6) 0.402(2) 0.08(2) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.432(6) . ?
N1 C2 1.451(6) . ?
N1 H1 0.86(6) . ?
N2 C6 1.361(6) . ?
N2 C13 1.503(7) . ?
C2 C3 1.448(7) . ?
C2 C6 1.496(7) . ?
C3 C4 1.467(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.477(7) . ?
C4 H4 0.9500 . ?
C5 C7 1.635(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C8 C9 1.3900 . ?
C8 H8 0.9500 . ?
C9 C10 1.3900 . ?
C9 H9 0.9500 . ?
C10 C11 1.3900 . ?
C10 H10 0.9500 . ?
C11 C12 1.3900 . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.467(7) . ?
C13 C18 1.486(7) . ?
C14 C15 1.466(8) . ?
C14 C19 1.585(8) . ?
C15 C16 1.460(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.447(8) . ?
C16 H16 0.9500 . ?
C17 C18 1.467(7) . ?
C17 H17 0.9500 . ?
C18 C20 1.582(7) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N3 C21 1.492(6) . ?
N3 H1N 0.889(19) . ?
N3 H2N 0.97(6) . ?
C21 C22 1.474(7) . ?
C21 C26 1.480(7) . ?
C22 C23 1.467(7) . ?
C22 C27 1.577(7) . ?
C23 C24 1.457(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.462(7) . ?
C24 H24 0.9500 . ?
C25 C26 1.478(7) . ?
C25 H25 0.9500 . ?
C26 C28 1.585(7) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 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
C5 N1 C2 110.6(4) . . ?
C5 N1 H1 132(4) . . ?
C2 N1 H1 116(4) . . ?
C6 N2 C13 121.1(4) . . ?
C3 C2 N1 107.1(4) . . ?
C3 C2 C6 128.5(5) . . ?
N1 C2 C6 124.3(4) . . ?
C2 C3 C4 108.0(4) . . ?
C2 C3 H3 126.0 . . ?
C4 C3 H3 126.0 . . ?
C3 C4 C5 107.9(5) . . ?
C3 C4 H4 126.0 . . ?
C5 C4 H4 126.0 . . ?
N1 C5 C4 106.3(5) . . ?
N1 C5 C7 123.7(4) . . ?
C4 C5 C7 129.9(4) . . ?
N2 C6 C2 126.1(5) . . ?
N2 C6 H6 116.9 . . ?
C2 C6 H6 116.9 . . ?
C8 C7 C12 120.0 . . ?
C8 C7 C5 119.3(3) . . ?
C12 C7 C5 120.7(3) . . ?
C7 C8 C9 120.0 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.0 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 120.0 . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
C14 C13 C18 121.9(5) . . ?
C14 C13 N2 121.0(5) . . ?
C18 C13 N2 117.0(5) . . ?
C15 C14 C13 117.3(5) . . ?
C15 C14 C19 119.8(5) . . ?
C13 C14 C19 122.9(5) . . ?
C16 C15 C14 122.1(6) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C17 C16 C15 119.3(6) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 121.4(5) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C13 117.9(5) . . ?
C17 C18 C20 121.8(5) . . ?
C13 C18 C20 120.3(5) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 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 N3 H1N 111(3) . . ?
C21 N3 H2N 112(3) . . ?
H1N N3 H2N 124(4) . . ?
C22 C21 C26 121.3(4) . . ?
C22 C21 N3 119.7(4) . . ?
C26 C21 N3 118.9(4) . . ?
C23 C22 C21 118.4(4) . . ?
C23 C22 C27 121.0(4) . . ?
C21 C22 C27 120.6(4) . . ?
C24 C23 C22 121.4(5) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C23 C24 C25 119.8(4) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C24 C25 C26 120.8(5) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C25 C26 C21 118.3(4) . . ?
C25 C26 C28 120.8(4) . . ?
C21 C26 C28 120.9(4) . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
C5 N1 C2 C3 0.2(5) . . . . ?
C5 N1 C2 C6 177.6(4) . . . . ?
N1 C2 C3 C4 0.1(5) . . . . ?
C6 C2 C3 C4 -177.0(4) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C2 N1 C5 C4 -0.5(5) . . . . ?
C2 N1 C5 C7 -179.6(4) . . . . ?
C3 C4 C5 N1 0.6(5) . . . . ?
C3 C4 C5 C7 179.6(4) . . . . ?
C13 N2 C6 C2 -177.4(4) . . . . ?
C3 C2 C6 N2 -179.4(5) . . . . ?
N1 C2 C6 N2 3.9(7) . . . . ?
N1 C5 C7 C8 -167.5(3) . . . . ?
C4 C5 C7 C8 13.7(6) . . . . ?
N1 C5 C7 C12 13.8(5) . . . . ?
C4 C5 C7 C12 -165.1(4) . . . . ?
C12 C7 C8 C9 0.0 . . . . ?
C5 C7 C8 C9 -178.7(3) . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 C7 0.0 . . . . ?
C8 C7 C12 C11 0.0 . . . . ?
C5 C7 C12 C11 178.7(3) . . . . ?
C6 N2 C13 C14 73.5(6) . . . . ?
C6 N2 C13 C18 -110.5(5) . . . . ?
C18 C13 C14 C15 -1.9(7) . . . . ?
N2 C13 C14 C15 173.9(4) . . . . ?
C18 C13 C14 C19 -180.0(5) . . . . ?
N2 C13 C14 C19 -4.1(7) . . . . ?
C13 C14 C15 C16 2.1(8) . . . . ?
C19 C14 C15 C16 -179.8(5) . . . . ?
C14 C15 C16 C17 -1.5(8) . . . . ?
C15 C16 C17 C18 0.6(8) . . . . ?
C16 C17 C18 C13 -0.4(7) . . . . ?
C16 C17 C18 C20 -179.6(5) . . . . ?
C14 C13 C18 C17 1.1(7) . . . . ?
N2 C13 C18 C17 -174.8(4) . . . . ?
C14 C13 C18 C20 -179.7(4) . . . . ?
N2 C13 C18 C20 4.3(6) . . . . ?
C26 C21 C22 C23 1.0(6) . . . . ?
N3 C21 C22 C23 -174.6(4) . . . . ?
C26 C21 C22 C27 -179.9(4) . . . . ?
N3 C21 C22 C27 4.5(6) . . . . ?
C21 C22 C23 C24 -0.5(7) . . . . ?
C27 C22 C23 C24 -179.6(4) . . . . ?
C22 C23 C24 C25 -0.7(7) . . . . ?
C23 C24 C25 C26 1.5(7) . . . . ?
C24 C25 C26 C21 -1.0(6) . . . . ?
C24 C25 C26 C28 178.2(4) . . . . ?
C22 C21 C26 C25 -0.2(6) . . . . ?
N3 C21 C26 C25 175.4(4) . . . . ?
C22 C21 C26 C28 -179.4(4) . . . . ?
N3 C21 C26 C28 -3.8(6) . . . . ?

_refine_diff_density_max         0.508
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.060

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

data_1A
_database_code_depnum_ccdc_archive 'CCDC 1853549'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C38 H34 N4 Ni'
_chemical_formula_sum            'C38 H34 N4 Ni'
_chemical_melting_point          ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            Green
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         605.40

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'
Ni Ni 0.3393 1.1124 '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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_H-M_alt        'P 42/n'
_space_group_name_Hall           '-P 4bc'
_chemical_absolute_configuration ?

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

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

_cell_length_a                   11.600(3)
_cell_length_b                   11.600(3)
_cell_length_c                   23.772(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3198.8(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2103
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      18.64
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             1272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.639
_shelx_estimated_absorpt_T_min   0.883
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_T_max  0.939
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36591
_diffrn_reflns_av_unetI/netI     0.0926
_diffrn_reflns_av_R_equivalents  0.1516
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.428
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2915
_reflns_number_gt                1191
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR92
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    Mercury
_computing_publication_material  enCIFer
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2915
_refine_ls_number_parameters     155
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.2082
_refine_ls_R_factor_gt           0.0974
_refine_ls_wR_factor_ref         0.3422
_refine_ls_wR_factor_gt          0.2898
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.250000 0.750000 0.37693(5) 0.0798(7) Uani 1 2 d S T P . .
N1 N 0.0994(5) 0.7317(6) 0.3421(3) 0.079(2) Uani 1 1 d . . . . .
N2 N 0.3362(5) 0.6416(5) 0.4297(2) 0.0693(17) Uani 1 1 d . . . . .
C2 C 0.0173(6) 0.7924(7) 0.3719(3) 0.071(2) Uani 1 1 d . . . . .
C3 C -0.0925(6) 0.7719(7) 0.3482(3) 0.075(2) Uani 1 1 d . . . . .
H3 H -0.163557 0.803823 0.360458 0.090 Uiso 1 1 calc R U . . .
C4 C -0.0771(6) 0.6976(6) 0.3042(3) 0.069(2) Uani 1 1 d . . . . .
H4 H -0.136056 0.667632 0.280592 0.083 Uiso 1 1 calc R U . . .
C5 C 0.0416(7) 0.6731(7) 0.2999(3) 0.076(2) Uani 1 1 d . . . . .
C6 C 0.4453(6) 0.6399(7) 0.4178(3) 0.075(2) Uani 1 1 d . . . . .
H6 H 0.498018 0.595029 0.439151 0.090 Uiso 1 1 calc R U . . .
C7 C 0.0992(6) 0.5979(7) 0.2585(3) 0.1421(19) Uani 1 1 d G . . . .
C8 C 0.0294(5) 0.5322(7) 0.2234(3) 0.1421(19) Uani 1 1 d G . . . .
H8 H -0.052053 0.538355 0.225940 0.171 Uiso 1 1 calc R U . . .
C9 C 0.0790(6) 0.4574(7) 0.1846(3) 0.1421(19) Uani 1 1 d G . . . .
H9 H 0.031295 0.412501 0.160644 0.171 Uiso 1 1 calc R U . . .
C10 C 0.1982(6) 0.4484(7) 0.1810(3) 0.1421(19) Uani 1 1 d G . . . .
H10 H 0.232040 0.397274 0.154452 0.171 Uiso 1 1 calc R U . . .
C11 C 0.2679(5) 0.5141(8) 0.2161(3) 0.1421(19) Uani 1 1 d G U . . .
H11 H 0.349440 0.507900 0.213557 0.171 Uiso 1 1 calc R U . . .
C12 C 0.2184(6) 0.5888(7) 0.2549(3) 0.1421(19) Uani 1 1 d G U . . .
H12 H 0.266094 0.633756 0.278854 0.171 Uiso 1 1 calc R U . . .
C13 C 0.2945(6) 0.5877(6) 0.4791(4) 0.071(2) Uani 1 1 d . . . . .
C14 C 0.3358(7) 0.6210(7) 0.5309(4) 0.078(2) Uani 1 1 d . . . . .
C15 C 0.2886(8) 0.5744(8) 0.5801(4) 0.096(3) Uani 1 1 d . . . . .
H15 H 0.313509 0.599562 0.616167 0.115 Uiso 1 1 calc R U . . .
C16 C 0.2029(9) 0.4890(9) 0.5746(5) 0.106(3) Uani 1 1 d . . . . .
H16 H 0.171611 0.454127 0.607324 0.128 Uiso 1 1 calc R U . . .
C17 C 0.1646(8) 0.4561(9) 0.5234(6) 0.114(4) Uani 1 1 d . . . . .
H17 H 0.106976 0.398007 0.521523 0.137 Uiso 1 1 calc R U . . .
C18 C 0.2054(7) 0.5029(8) 0.4731(5) 0.100(3) Uani 1 1 d . . . . .
C19 C 0.1646(9) 0.4634(10) 0.4179(4) 0.129(4) Uani 1 1 d . . . . .
H19A H 0.230926 0.444868 0.394035 0.193 Uiso 1 1 calc R U . . .
H19B H 0.118951 0.524472 0.400155 0.193 Uiso 1 1 calc R U . . .
H19C H 0.116713 0.394501 0.422702 0.193 Uiso 1 1 calc R U . . .
C20 C 0.4257(7) 0.7146(8) 0.5366(4) 0.093(3) Uani 1 1 d . . . . .
H20A H 0.502723 0.679901 0.536531 0.139 Uiso 1 1 calc R U . . .
H20B H 0.413727 0.756184 0.572033 0.139 Uiso 1 1 calc R U . . .
H20C H 0.418948 0.768484 0.505030 0.139 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 N1 1.945(5) 2_565 ?
Ni1 N1 1.945(5) . ?
Ni1 N2 2.038(6) 2_565 ?
Ni1 N2 2.038(6) . ?
N1 C2 1.380(9) . ?
N1 C5 1.385(9) . ?
N2 C6 1.297(8) . ?
N2 C13 1.416(9) . ?
C2 C6 1.413(10) 2_565 ?
C2 C3 1.413(9) . ?
C3 C4 1.368(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.409(10) . ?
C4 H4 0.9500 . ?
C5 C7 1.475(9) . ?
C6 H6 0.9500 . ?
C7 C8 1.3900 . ?
C7 C12 1.3900 . ?
C8 C9 1.3900 . ?
C8 H8 0.9500 . ?
C9 C10 1.3900 . ?
C9 H9 0.9500 . ?
C10 C11 1.3900 . ?
C10 H10 0.9500 . ?
C11 C12 1.3900 . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.376(10) . ?
C13 C18 1.434(11) . ?
C14 C15 1.402(11) . ?
C14 C20 1.512(11) . ?
C15 C16 1.409(13) . ?
C15 H15 0.9500 . ?
C16 C17 1.350(13) . ?
C16 H16 0.9500 . ?
C17 C18 1.395(13) . ?
C17 H17 0.9500 . ?
C18 C19 1.469(13) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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 N1 129.6(4) 2_565 . ?
N1 Ni1 N2 129.5(3) 2_565 2_565 ?
N1 Ni1 N2 83.6(3) . 2_565 ?
N1 Ni1 N2 83.6(3) 2_565 . ?
N1 Ni1 N2 129.5(3) . . ?
N2 Ni1 N2 104.0(3) 2_565 . ?
C2 N1 C5 106.7(6) . . ?
C2 N1 Ni1 110.2(5) . . ?
C5 N1 Ni1 142.9(5) . . ?
C6 N2 C13 120.5(7) . . ?
C6 N2 Ni1 110.7(5) . . ?
C13 N2 Ni1 128.0(5) . . ?
N1 C2 C6 117.9(6) . 2_565 ?
N1 C2 C3 109.3(7) . . ?
C6 C2 C3 132.7(8) 2_565 . ?
C4 C3 C2 107.1(7) . . ?
C4 C3 H3 126.5 . . ?
C2 C3 H3 126.5 . . ?
C3 C4 C5 108.0(6) . . ?
C3 C4 H4 126.0 . . ?
C5 C4 H4 126.0 . . ?
N1 C5 C4 108.8(7) . . ?
N1 C5 C7 123.6(7) . . ?
C4 C5 C7 127.6(7) . . ?
N2 C6 C2 117.4(7) . 2_565 ?
N2 C6 H6 121.3 . . ?
C2 C6 H6 121.3 2_565 . ?
C8 C7 C12 120.0 . . ?
C8 C7 C5 117.5(6) . . ?
C12 C7 C5 122.5(6) . . ?
C7 C8 C9 120.0 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 120.0 . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
C14 C13 N2 119.9(6) . . ?
C14 C13 C18 122.2(8) . . ?
N2 C13 C18 117.9(8) . . ?
C13 C14 C15 120.2(7) . . ?
C13 C14 C20 121.5(7) . . ?
C15 C14 C20 118.1(8) . . ?
C14 C15 C16 117.9(9) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
C17 C16 C15 121.1(9) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 123.3(9) . . ?
C16 C17 H17 118.3 . . ?
C18 C17 H17 118.3 . . ?
C17 C18 C19 122.3(9) . . ?
C17 C18 C13 115.3(9) . . ?
C19 C18 C13 122.3(9) . . ?
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 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C14 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
C5 N1 C2 C6 179.9(7) . . . 2_565 ?
Ni1 N1 C2 C6 3.9(9) . . . 2_565 ?
C5 N1 C2 C3 -0.1(9) . . . . ?
Ni1 N1 C2 C3 -176.1(5) . . . . ?
N1 C2 C3 C4 0.6(9) . . . . ?
C6 C2 C3 C4 -179.4(8) 2_565 . . . ?
C2 C3 C4 C5 -0.9(9) . . . . ?
C2 N1 C5 C4 -0.4(8) . . . . ?
Ni1 N1 C5 C4 173.4(7) . . . . ?
C2 N1 C5 C7 179.9(7) . . . . ?
Ni1 N1 C5 C7 -6.2(13) . . . . ?
C3 C4 C5 N1 0.8(9) . . . . ?
C3 C4 C5 C7 -179.6(8) . . . . ?
C13 N2 C6 C2 -172.2(7) . . . 2_565 ?
Ni1 N2 C6 C2 -1.6(9) . . . 2_565 ?
N1 C5 C7 C8 171.4(6) . . . . ?
C4 C5 C7 C8 -8.2(10) . . . . ?
N1 C5 C7 C12 -6.9(10) . . . . ?
C4 C5 C7 C12 173.6(6) . . . . ?
C12 C7 C8 C9 0.0 . . . . ?
C5 C7 C8 C9 -178.3(7) . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 C7 0.0 . . . . ?
C8 C7 C12 C11 0.0 . . . . ?
C5 C7 C12 C11 178.2(8) . . . . ?
C6 N2 C13 C14 58.1(10) . . . . ?
Ni1 N2 C13 C14 -110.7(7) . . . . ?
C6 N2 C13 C18 -124.8(8) . . . . ?
Ni1 N2 C13 C18 66.4(9) . . . . ?
N2 C13 C14 C15 175.1(7) . . . . ?
C18 C13 C14 C15 -1.9(13) . . . . ?
N2 C13 C14 C20 0.0(12) . . . . ?
C18 C13 C14 C20 -177.0(8) . . . . ?
C13 C14 C15 C16 3.3(13) . . . . ?
C20 C14 C15 C16 178.6(8) . . . . ?
C14 C15 C16 C17 -2.3(15) . . . . ?
C15 C16 C17 C18 -0.2(17) . . . . ?
C16 C17 C18 C19 178.3(11) . . . . ?
C16 C17 C18 C13 1.7(15) . . . . ?
C14 C13 C18 C17 -0.6(12) . . . . ?
N2 C13 C18 C17 -177.6(7) . . . . ?
C14 C13 C18 C19 -177.2(9) . . . . ?
N2 C13 C18 C19 5.7(13) . . . . ?

_refine_diff_density_max         1.048
_refine_diff_density_min         -0.789
_refine_diff_density_rms         0.091

####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1853555'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C56 H63 N2 Ni P'
_chemical_formula_sum            'C56 H63 N2 Ni P'
_chemical_melting_point          ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         853.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   10.1181(8)
_cell_length_b                   13.5337(9)
_cell_length_c                   19.3762(16)
_cell_angle_alpha                108.714(3)
_cell_angle_beta                 94.968(3)
_cell_angle_gamma                106.611(3)
_cell_volume                     2361.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3685
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      23.58
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.483
_shelx_estimated_absorpt_T_min   0.853
_shelx_estimated_absorpt_T_max   0.877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.853
_exptl_absorpt_correction_T_max  0.877
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24486
_diffrn_reflns_av_unetI/netI     0.0863
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.963
_diffrn_reflns_theta_max         25.761
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9000
_reflns_number_gt                6354
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2014
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0541P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9000
_refine_ls_number_parameters     551
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
NI1 Ni 0.21728(4) 0.11356(3) 0.76494(2) 0.01866(11) Uani 1 1 d . . . . .
P1 P 0.14523(8) 0.05907(5) 0.85207(4) 0.01996(17) Uani 1 1 d . . . . .
N2 N 0.2063(2) 0.21897(17) 0.71539(12) 0.0221(5) Uani 1 1 d . . . . .
N1 N 0.0843(2) 0.00535(17) 0.67407(11) 0.0195(5) Uani 1 1 d . . . . .
C39 C 0.4917(3) 0.1567(2) 0.83160(15) 0.0283(7) Uani 1 1 d . . . . .
H39 H 0.469104 0.080309 0.803094 0.034 Uiso 1 1 calc R U . . .
C2 C 0.0236(3) 0.0611(2) 0.63904(14) 0.0223(6) Uani 1 1 d . . . . .
C6 C 0.0955(3) 0.1752(2) 0.66189(14) 0.0229(6) Uani 1 1 d . . . . .
H6 H 0.064396 0.219266 0.639101 0.027 Uiso 1 1 calc R U . . .
C34 C 0.3877(3) 0.2054(2) 0.83243(14) 0.0226(6) Uani 1 1 d . . . . .
C46 C 0.2128(3) -0.0376(2) 0.87840(14) 0.0220(6) Uani 1 1 d . . . . .
C5 C 0.0167(3) -0.1044(2) 0.63423(14) 0.0222(6) Uani 1 1 d . . . . .
C7 C 0.0735(3) -0.1937(2) 0.63710(14) 0.0220(6) Uani 1 1 d . . . . .
C8 C 0.1927(3) -0.1980(2) 0.60563(15) 0.0252(6) Uani 1 1 d . . . . .
C12 C 0.0049(3) -0.2787(2) 0.66122(14) 0.0248(6) Uani 1 1 d . . . . .
C52 C -0.0464(3) -0.0027(2) 0.83094(14) 0.0235(6) Uani 1 1 d . . . . .
C51 C 0.2534(3) -0.1131(2) 0.82488(15) 0.0241(6) Uani 1 1 d . . . . .
H51 H 0.245466 -0.113397 0.775587 0.029 Uiso 1 1 calc R U . . .
C22 C 0.2859(3) 0.3332(2) 0.73521(14) 0.0215(6) Uani 1 1 d . . . . .
C35 C 0.4256(3) 0.3168(2) 0.87685(15) 0.0280(7) Uani 1 1 d . . . . .
H35 H 0.356631 0.352293 0.879669 0.034 Uiso 1 1 calc R U . . .
C50 C 0.3052(3) -0.1878(2) 0.84250(17) 0.0302(7) Uani 1 1 d . . . . .
H50 H 0.330361 -0.240448 0.805043 0.036 Uiso 1 1 calc R U . . .
C16 C 0.2688(3) -0.1127(2) 0.57460(16) 0.0304(7) Uani 1 1 d . . . . .
H16 H 0.221320 -0.055594 0.583177 0.037 Uiso 1 1 calc R U . . .
C3 C -0.0841(3) -0.0135(2) 0.57987(16) 0.0304(7) Uani 1 1 d . . . . .
H3 H -0.143147 0.003600 0.547836 0.037 Uiso 1 1 calc R U . . .
C27 C 0.2389(3) 0.4160(2) 0.77968(15) 0.0247(6) Uani 1 1 d . . . . .
C11 C 0.0550(3) -0.3662(2) 0.65202(15) 0.0276(7) Uani 1 1 d . . . . .
H11 H 0.007969 -0.423458 0.668462 0.033 Uiso 1 1 calc R U . . .
C23 C 0.4135(3) 0.3585(2) 0.71224(15) 0.0244(6) Uani 1 1 d . . . . .
C9 C 0.2395(3) -0.2883(2) 0.59868(15) 0.0290(7) Uani 1 1 d . . . . .
H9 H 0.321544 -0.290392 0.578645 0.035 Uiso 1 1 calc R U . . .
C10 C 0.1703(3) -0.3742(2) 0.62000(14) 0.0262(7) Uani 1 1 d . . . . .
C19 C 0.2128(3) -0.4773(2) 0.60697(16) 0.0355(8) Uani 1 1 d . . . . .
H19 H 0.230790 -0.484734 0.656313 0.043 Uiso 1 1 calc R U . . .
C53 C -0.1236(3) 0.0261(2) 0.78246(15) 0.0272(7) Uani 1 1 d . . . . .
H53 H -0.075759 0.074798 0.759762 0.033 Uiso 1 1 calc R U . . .
C40 C 0.1708(3) 0.1717(2) 0.94050(14) 0.0247(6) Uani 1 1 d . . . . .
C31 C 0.4637(3) 0.2667(2) 0.66673(16) 0.0306(7) Uani 1 1 d . . . . .
H31 H 0.417367 0.199664 0.678362 0.037 Uiso 1 1 calc R U . . .
C4 C -0.0879(3) -0.1174(2) 0.57713(15) 0.0298(7) Uani 1 1 d . . . . .
H4 H -0.150734 -0.185734 0.542431 0.036 Uiso 1 1 calc R U . . .
C56 C -0.2643(3) -0.1103(3) 0.84963(18) 0.0404(8) Uani 1 1 d . . . . .
H56 H -0.313423 -0.156978 0.873281 0.049 Uiso 1 1 calc R U . . .
C57 C -0.1193(3) -0.0708(2) 0.86524(15) 0.0306(7) Uani 1 1 d . . . . .
H57 H -0.069109 -0.090326 0.899610 0.037 Uiso 1 1 calc R U . . .
C47 C 0.2258(3) -0.0386(2) 0.95027(16) 0.0354(8) Uani 1 1 d . . . . .
H47 H 0.196469 0.011263 0.987454 0.042 Uiso 1 1 calc R U . . .
C26 C 0.3208(3) 0.5249(2) 0.79628(16) 0.0321(7) Uani 1 1 d . . . . .
H26 H 0.290752 0.582572 0.825327 0.038 Uiso 1 1 calc R U . . .
C25 C 0.4452(3) 0.5514(2) 0.77158(16) 0.0369(8) Uani 1 1 d . . . . .
H25 H 0.498700 0.626699 0.782655 0.044 Uiso 1 1 calc R U . . .
C36 C 0.5609(3) 0.3772(2) 0.91699(16) 0.0359(8) Uani 1 1 d . . . . .
H36 H 0.583876 0.453125 0.946640 0.043 Uiso 1 1 calc R U . . .
C54 C -0.2681(3) -0.0147(3) 0.76671(18) 0.0406(8) Uani 1 1 d . . . . .
H54 H -0.319441 0.004345 0.732473 0.049 Uiso 1 1 calc R U . . .
C24 C 0.4921(3) 0.4687(2) 0.73073(16) 0.0339(7) Uani 1 1 d . . . . .
H24 H 0.579404 0.487591 0.715164 0.041 Uiso 1 1 calc R U . . .
C37 C 0.6627(3) 0.3269(3) 0.91393(17) 0.0396(8) Uani 1 1 d . . . . .
H37 H 0.755905 0.368092 0.941043 0.047 Uiso 1 1 calc R U . . .
C13 C -0.1247(3) -0.2783(2) 0.69497(16) 0.0299(7) Uani 1 1 d . . . . .
H13 H -0.123953 -0.200114 0.714742 0.036 Uiso 1 1 calc R U . . .
C49 C 0.3204(3) -0.1863(2) 0.91384(17) 0.0361(8) Uani 1 1 d . . . . .
H49 H 0.358102 -0.236748 0.925994 0.043 Uiso 1 1 calc R U . . .
C45 C 0.0621(4) 0.2113(2) 0.96108(17) 0.0377(8) Uani 1 1 d . . . . .
H45 H -0.029010 0.176968 0.930347 0.045 Uiso 1 1 calc R U . . .
C28 C 0.1058(3) 0.3887(2) 0.80936(16) 0.0338(7) Uani 1 1 d . . . . .
H28 H 0.078234 0.309257 0.804280 0.041 Uiso 1 1 calc R U . . .
C48 C 0.2812(4) -0.1119(3) 0.96784(18) 0.0437(9) Uani 1 1 d . . . . .
H48 H 0.292165 -0.110786 1.017309 0.052 Uiso 1 1 calc R U . . .
C41 C 0.3025(4) 0.2234(2) 0.98718(16) 0.0357(8) Uani 1 1 d . . . . .
H41 H 0.377987 0.197083 0.974618 0.043 Uiso 1 1 calc R U . . .
C17 C 0.2579(4) -0.1653(3) 0.49085(17) 0.0429(8) Uani 1 1 d . . . . .
H17A H 0.299591 -0.224292 0.480661 0.064 Uiso 1 1 calc R U . . .
H17B H 0.308334 -0.108930 0.472161 0.064 Uiso 1 1 calc R U . . .
H17C H 0.158715 -0.196399 0.466019 0.064 Uiso 1 1 calc R U . . .
C38 C 0.6276(3) 0.2169(3) 0.87135(17) 0.0366(8) Uani 1 1 d . . . . .
H38 H 0.696944 0.181823 0.869082 0.044 Uiso 1 1 calc R U . . .
C42 C 0.3240(4) 0.3130(3) 1.05169(17) 0.0482(9) Uani 1 1 d . . . . .
H42 H 0.414524 0.347923 1.082954 0.058 Uiso 1 1 calc R U . . .
C14 C -0.2590(3) -0.3466(3) 0.63672(19) 0.0511(9) Uani 1 1 d . . . . .
H14A H -0.257560 -0.320063 0.595198 0.077 Uiso 1 1 calc R U . . .
H14B H -0.340671 -0.339078 0.658980 0.077 Uiso 1 1 calc R U . . .
H14C H -0.265194 -0.424494 0.618517 0.077 Uiso 1 1 calc R U . . .
C32 C 0.6211(3) 0.2926(3) 0.68719(19) 0.0484(9) Uani 1 1 d . . . . .
H32A H 0.670624 0.355714 0.674151 0.073 Uiso 1 1 calc R U . . .
H32B H 0.646182 0.228038 0.659919 0.073 Uiso 1 1 calc R U . . .
H32C H 0.648283 0.310752 0.740727 0.073 Uiso 1 1 calc R U . . .
C55 C -0.3379(4) -0.0828(3) 0.80048(19) 0.0457(9) Uani 1 1 d . . . . .
H55 H -0.437762 -0.110970 0.789705 0.055 Uiso 1 1 calc R U . . .
C15 C -0.1266(4) -0.3200(2) 0.75941(17) 0.0401(8) Uani 1 1 d . . . . .
H15A H -0.138177 -0.398939 0.740547 0.060 Uiso 1 1 calc R U . . .
H15B H -0.205048 -0.308729 0.783616 0.060 Uiso 1 1 calc R U . . .
H15C H -0.037838 -0.278969 0.795469 0.060 Uiso 1 1 calc R U . . .
C44 C 0.0866(4) 0.3011(3) 1.02670(19) 0.0508(10) Uani 1 1 d . . . . .
H44 H 0.011562 0.327287 1.040612 0.061 Uiso 1 1 calc R U . . .
C21 C 0.0927(4) -0.5807(2) 0.55715(19) 0.0495(10) Uani 1 1 d . . . . .
H21A H 0.076476 -0.578684 0.507091 0.074 Uiso 1 1 calc R U . . .
H21B H 0.007028 -0.583380 0.577606 0.074 Uiso 1 1 calc R U . . .
H21C H 0.117365 -0.646520 0.554734 0.074 Uiso 1 1 calc R U . . .
C30 C 0.1249(4) 0.4588(3) 0.89222(18) 0.0495(9) Uani 1 1 d . . . . .
H30A H 0.203642 0.451225 0.920928 0.074 Uiso 1 1 calc R U . . .
H30B H 0.038708 0.433049 0.910181 0.074 Uiso 1 1 calc R U . . .
H30C H 0.144678 0.536634 0.898211 0.074 Uiso 1 1 calc R U . . .
C33 C 0.4154(4) 0.2371(3) 0.58407(17) 0.0493(10) Uani 1 1 d . . . . .
H33A H 0.462382 0.299667 0.569868 0.074 Uiso 1 1 calc R U . . .
H33B H 0.313349 0.220256 0.572874 0.074 Uiso 1 1 calc R U . . .
H33C H 0.439335 0.172304 0.556107 0.074 Uiso 1 1 calc R U . . .
C43 C 0.2166(5) 0.3520(3) 1.07120(18) 0.0506(10) Uani 1 1 d . . . . .
H43 H 0.232671 0.414007 1.115450 0.061 Uiso 1 1 calc R U . . .
C20 C 0.3456(4) -0.4704(3) 0.5765(2) 0.0569(11) Uani 1 1 d . . . . .
H20A H 0.331433 -0.464012 0.527670 0.085 Uiso 1 1 calc R U . . .
H20B H 0.369421 -0.537295 0.571648 0.085 Uiso 1 1 calc R U . . .
H20C H 0.422540 -0.405391 0.610449 0.085 Uiso 1 1 calc R U . . .
C18 C 0.4221(4) -0.0544(3) 0.6142(2) 0.0523(9) Uani 1 1 d . . . . .
H18A H 0.426568 -0.017146 0.667280 0.078 Uiso 1 1 calc R U . . .
H18B H 0.467528 0.000396 0.593081 0.078 Uiso 1 1 calc R U . . .
H18C H 0.470740 -0.108854 0.607666 0.078 Uiso 1 1 calc R U . . .
C29 C -0.0135(4) 0.4030(4) 0.7654(2) 0.0738(13) Uani 1 1 d . . . . .
H29A H 0.009298 0.480990 0.771063 0.111 Uiso 1 1 calc R U . . .
H29B H -0.099939 0.379671 0.783814 0.111 Uiso 1 1 calc R U . . .
H29C H -0.027303 0.357729 0.712767 0.111 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 C34 1.889(3) . ?
NI1 N1 1.966(2) . ?
NI1 N2 1.980(2) . ?
NI1 P1 2.1518(8) . ?
P1 C46 1.822(2) . ?
P1 C52 1.828(3) . ?
P1 C40 1.830(3) . ?
N2 C6 1.307(3) . ?
N2 C22 1.428(3) . ?
N1 C5 1.364(3) . ?
N1 C2 1.390(3) . ?
C39 C38 1.386(4) . ?
C39 C34 1.391(4) . ?
C39 H39 0.9500 . ?
C2 C3 1.390(4) . ?
C2 C6 1.404(4) . ?
C6 H6 0.9500 . ?
C34 C35 1.393(4) . ?
C46 C51 1.386(4) . ?
C46 C47 1.392(4) . ?
C5 C4 1.393(4) . ?
C5 C7 1.493(3) . ?
C7 C12 1.403(4) . ?
C7 C8 1.405(4) . ?
C8 C9 1.405(3) . ?
C8 C16 1.518(4) . ?
C12 C11 1.384(3) . ?
C12 C13 1.516(4) . ?
C52 C57 1.387(4) . ?
C52 C53 1.388(4) . ?
C51 C50 1.382(4) . ?
C51 H51 0.9500 . ?
C22 C23 1.388(4) . ?
C22 C27 1.408(4) . ?
C35 C36 1.384(4) . ?
C35 H35 0.9500 . ?
C50 C49 1.370(4) . ?
C50 H50 0.9500 . ?
C16 C18 1.524(4) . ?
C16 C17 1.528(4) . ?
C16 H16 1.0000 . ?
C3 C4 1.379(4) . ?
C3 H3 0.9500 . ?
C27 C26 1.383(4) . ?
C27 C28 1.506(4) . ?
C11 C10 1.383(4) . ?
C11 H11 0.9500 . ?
C23 C24 1.384(4) . ?
C23 C31 1.521(4) . ?
C9 C10 1.379(4) . ?
C9 H9 0.9500 . ?
C10 C19 1.527(4) . ?
C19 C20 1.504(5) . ?
C19 C21 1.525(4) . ?
C19 H19 1.0000 . ?
C53 C54 1.375(4) . ?
C53 H53 0.9500 . ?
C40 C45 1.389(4) . ?
C40 C41 1.391(4) . ?
C31 C32 1.516(4) . ?
C31 C33 1.519(4) . ?
C31 H31 1.0000 . ?
C4 H4 0.9500 . ?
C56 C55 1.365(5) . ?
C56 C57 1.379(4) . ?
C56 H56 0.9500 . ?
C57 H57 0.9500 . ?
C47 C48 1.384(4) . ?
C47 H47 0.9500 . ?
C26 C25 1.377(4) . ?
C26 H26 0.9500 . ?
C25 C24 1.381(4) . ?
C25 H25 0.9500 . ?
C36 C37 1.382(4) . ?
C36 H36 0.9500 . ?
C54 C55 1.367(5) . ?
C54 H54 0.9500 . ?
C24 H24 0.9500 . ?
C37 C38 1.371(4) . ?
C37 H37 0.9500 . ?
C13 C14 1.524(4) . ?
C13 C15 1.526(4) . ?
C13 H13 1.0000 . ?
C49 C48 1.375(4) . ?
C49 H49 0.9500 . ?
C45 C44 1.392(4) . ?
C45 H45 0.9500 . ?
C28 C29 1.510(4) . ?
C28 C30 1.542(4) . ?
C28 H28 1.0000 . ?
C48 H48 0.9500 . ?
C41 C42 1.381(4) . ?
C41 H41 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C38 H38 0.9500 . ?
C42 C43 1.368(5) . ?
C42 H42 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C55 H55 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C44 C43 1.361(5) . ?
C44 H44 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C43 H43 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 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
C34 NI1 N1 160.98(10) . . ?
C34 NI1 N2 96.10(10) . . ?
N1 NI1 N2 82.94(9) . . ?
C34 NI1 P1 88.25(8) . . ?
N1 NI1 P1 104.21(7) . . ?
N2 NI1 P1 142.11(7) . . ?
C46 P1 C52 106.18(13) . . ?
C46 P1 C40 103.69(12) . . ?
C52 P1 C40 100.56(13) . . ?
C46 P1 NI1 120.01(9) . . ?
C52 P1 NI1 110.37(9) . . ?
C40 P1 NI1 114.01(9) . . ?
C6 N2 C22 118.5(2) . . ?
C6 N2 NI1 110.38(18) . . ?
C22 N2 NI1 130.56(16) . . ?
C5 N1 C2 105.5(2) . . ?
C5 N1 NI1 145.16(17) . . ?
C2 N1 NI1 108.89(16) . . ?
C38 C39 C34 121.6(3) . . ?
C38 C39 H39 119.2 . . ?
C34 C39 H39 119.2 . . ?
N1 C2 C3 110.5(2) . . ?
N1 C2 C6 115.1(2) . . ?
C3 C2 C6 133.5(2) . . ?
N2 C6 C2 118.2(2) . . ?
N2 C6 H6 120.9 . . ?
C2 C6 H6 120.9 . . ?
C39 C34 C35 116.8(3) . . ?
C39 C34 NI1 114.6(2) . . ?
C35 C34 NI1 128.4(2) . . ?
C51 C46 C47 118.6(2) . . ?
C51 C46 P1 118.8(2) . . ?
C47 C46 P1 122.7(2) . . ?
N1 C5 C4 110.0(2) . . ?
N1 C5 C7 123.9(2) . . ?
C4 C5 C7 123.9(2) . . ?
C12 C7 C8 119.5(2) . . ?
C12 C7 C5 123.2(2) . . ?
C8 C7 C5 116.8(2) . . ?
C7 C8 C9 118.8(3) . . ?
C7 C8 C16 123.0(2) . . ?
C9 C8 C16 118.1(3) . . ?
C11 C12 C7 118.9(3) . . ?
C11 C12 C13 119.5(3) . . ?
C7 C12 C13 121.5(2) . . ?
C57 C52 C53 118.1(3) . . ?
C57 C52 P1 123.1(2) . . ?
C53 C52 P1 118.7(2) . . ?
C50 C51 C46 120.7(3) . . ?
C50 C51 H51 119.7 . . ?
C46 C51 H51 119.7 . . ?
C23 C22 C27 121.8(2) . . ?
C23 C22 N2 117.5(2) . . ?
C27 C22 N2 120.6(2) . . ?
C36 C35 C34 121.8(3) . . ?
C36 C35 H35 119.1 . . ?
C34 C35 H35 119.1 . . ?
C49 C50 C51 120.2(3) . . ?
C49 C50 H50 119.9 . . ?
C51 C50 H50 119.9 . . ?
C8 C16 C18 111.7(2) . . ?
C8 C16 C17 110.9(2) . . ?
C18 C16 C17 110.8(3) . . ?
C8 C16 H16 107.7 . . ?
C18 C16 H16 107.7 . . ?
C17 C16 H16 107.7 . . ?
C4 C3 C2 106.1(2) . . ?
C4 C3 H3 127.0 . . ?
C2 C3 H3 127.0 . . ?
C26 C27 C22 117.4(3) . . ?
C26 C27 C28 120.6(3) . . ?
C22 C27 C28 122.0(2) . . ?
C10 C11 C12 123.0(3) . . ?
C10 C11 H11 118.5 . . ?
C12 C11 H11 118.5 . . ?
C24 C23 C22 118.4(3) . . ?
C24 C23 C31 121.1(3) . . ?
C22 C23 C31 120.4(2) . . ?
C10 C9 C8 122.1(3) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C9 C10 C11 117.4(2) . . ?
C9 C10 C19 122.7(3) . . ?
C11 C10 C19 119.8(3) . . ?
C20 C19 C21 110.7(3) . . ?
C20 C19 C10 113.5(3) . . ?
C21 C19 C10 110.7(2) . . ?
C20 C19 H19 107.2 . . ?
C21 C19 H19 107.2 . . ?
C10 C19 H19 107.2 . . ?
C54 C53 C52 121.1(3) . . ?
C54 C53 H53 119.4 . . ?
C52 C53 H53 119.4 . . ?
C45 C40 C41 118.4(3) . . ?
C45 C40 P1 121.3(2) . . ?
C41 C40 P1 120.3(2) . . ?
C32 C31 C33 111.8(3) . . ?
C32 C31 C23 113.0(2) . . ?
C33 C31 C23 111.0(2) . . ?
C32 C31 H31 106.9 . . ?
C33 C31 H31 106.9 . . ?
C23 C31 H31 106.9 . . ?
C3 C4 C5 107.9(2) . . ?
C3 C4 H4 126.0 . . ?
C5 C4 H4 126.0 . . ?
C55 C56 C57 120.5(3) . . ?
C55 C56 H56 119.7 . . ?
C57 C56 H56 119.7 . . ?
C56 C57 C52 120.3(3) . . ?
C56 C57 H57 119.9 . . ?
C52 C57 H57 119.9 . . ?
C48 C47 C46 120.4(3) . . ?
C48 C47 H47 119.8 . . ?
C46 C47 H47 119.8 . . ?
C25 C26 C27 121.4(3) . . ?
C25 C26 H26 119.3 . . ?
C27 C26 H26 119.3 . . ?
C26 C25 C24 120.1(3) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C37 C36 C35 120.0(3) . . ?
C37 C36 H36 120.0 . . ?
C35 C36 H36 120.0 . . ?
C55 C54 C53 119.8(3) . . ?
C55 C54 H54 120.1 . . ?
C53 C54 H54 120.1 . . ?
C25 C24 C23 120.7(3) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C38 C37 C36 119.3(3) . . ?
C38 C37 H37 120.3 . . ?
C36 C37 H37 120.3 . . ?
C12 C13 C14 111.3(2) . . ?
C12 C13 C15 112.5(2) . . ?
C14 C13 C15 109.5(3) . . ?
C12 C13 H13 107.8 . . ?
C14 C13 H13 107.8 . . ?
C15 C13 H13 107.8 . . ?
C50 C49 C48 120.0(3) . . ?
C50 C49 H49 120.0 . . ?
C48 C49 H49 120.0 . . ?
C40 C45 C44 120.0(3) . . ?
C40 C45 H45 120.0 . . ?
C44 C45 H45 120.0 . . ?
C27 C28 C29 111.5(3) . . ?
C27 C28 C30 112.5(3) . . ?
C29 C28 C30 109.1(3) . . ?
C27 C28 H28 107.8 . . ?
C29 C28 H28 107.8 . . ?
C30 C28 H28 107.8 . . ?
C49 C48 C47 120.1(3) . . ?
C49 C48 H48 119.9 . . ?
C47 C48 H48 119.9 . . ?
C42 C41 C40 120.3(3) . . ?
C42 C41 H41 119.9 . . ?
C40 C41 H41 119.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C37 C38 C39 120.5(3) . . ?
C37 C38 H38 119.8 . . ?
C39 C38 H38 119.8 . . ?
C43 C42 C41 120.9(3) . . ?
C43 C42 H42 119.5 . . ?
C41 C42 H42 119.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C56 C55 C54 120.2(3) . . ?
C56 C55 H55 119.9 . . ?
C54 C55 H55 119.9 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C43 C44 C45 120.9(3) . . ?
C43 C44 H44 119.6 . . ?
C45 C44 H44 119.6 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C44 C43 C42 119.5(3) . . ?
C44 C43 H43 120.3 . . ?
C42 C43 H43 120.3 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 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
C5 N1 C2 C3 2.3(3) . . . . ?
NI1 N1 C2 C3 -172.3(2) . . . . ?
C5 N1 C2 C6 -168.1(2) . . . . ?
NI1 N1 C2 C6 17.4(3) . . . . ?
C22 N2 C6 C2 175.5(2) . . . . ?
NI1 N2 C6 C2 -12.5(3) . . . . ?
N1 C2 C6 N2 -3.4(4) . . . . ?
C3 C2 C6 N2 -170.8(3) . . . . ?
C38 C39 C34 C35 -1.8(4) . . . . ?
C38 C39 C34 NI1 172.4(2) . . . . ?
N1 NI1 C34 C39 -40.4(4) . . . . ?
N2 NI1 C34 C39 -126.4(2) . . . . ?
P1 NI1 C34 C39 91.3(2) . . . . ?
N1 NI1 C34 C35 133.1(3) . . . . ?
N2 NI1 C34 C35 47.0(3) . . . . ?
P1 NI1 C34 C35 -95.2(3) . . . . ?
C52 P1 C46 C51 95.9(2) . . . . ?
C40 P1 C46 C51 -158.7(2) . . . . ?
NI1 P1 C46 C51 -30.0(3) . . . . ?
C52 P1 C46 C47 -84.3(3) . . . . ?
C40 P1 C46 C47 21.2(3) . . . . ?
NI1 P1 C46 C47 149.8(2) . . . . ?
C2 N1 C5 C4 -2.2(3) . . . . ?
NI1 N1 C5 C4 168.8(2) . . . . ?
C2 N1 C5 C7 161.1(2) . . . . ?
NI1 N1 C5 C7 -27.9(5) . . . . ?
N1 C5 C7 C12 118.6(3) . . . . ?
C4 C5 C7 C12 -80.3(4) . . . . ?
N1 C5 C7 C8 -69.0(3) . . . . ?
C4 C5 C7 C8 92.0(3) . . . . ?
C12 C7 C8 C9 0.4(4) . . . . ?
C5 C7 C8 C9 -172.2(2) . . . . ?
C12 C7 C8 C16 176.8(3) . . . . ?
C5 C7 C8 C16 4.2(4) . . . . ?
C8 C7 C12 C11 -1.2(4) . . . . ?
C5 C7 C12 C11 170.9(2) . . . . ?
C8 C7 C12 C13 -179.5(2) . . . . ?
C5 C7 C12 C13 -7.4(4) . . . . ?
C46 P1 C52 C57 30.5(3) . . . . ?
C40 P1 C52 C57 -77.2(2) . . . . ?
NI1 P1 C52 C57 162.1(2) . . . . ?
C46 P1 C52 C53 -154.4(2) . . . . ?
C40 P1 C52 C53 97.9(2) . . . . ?
NI1 P1 C52 C53 -22.8(2) . . . . ?
C47 C46 C51 C50 0.2(4) . . . . ?
P1 C46 C51 C50 180.0(2) . . . . ?
C6 N2 C22 C23 -104.7(3) . . . . ?
NI1 N2 C22 C23 85.2(3) . . . . ?
C6 N2 C22 C27 78.5(3) . . . . ?
NI1 N2 C22 C27 -91.7(3) . . . . ?
C39 C34 C35 C36 1.4(4) . . . . ?
NI1 C34 C35 C36 -171.8(2) . . . . ?
C46 C51 C50 C49 -1.6(4) . . . . ?
C7 C8 C16 C18 120.6(3) . . . . ?
C9 C8 C16 C18 -63.0(3) . . . . ?
C7 C8 C16 C17 -115.3(3) . . . . ?
C9 C8 C16 C17 61.2(3) . . . . ?
N1 C2 C3 C4 -1.4(3) . . . . ?
C6 C2 C3 C4 166.5(3) . . . . ?
C23 C22 C27 C26 3.7(4) . . . . ?
N2 C22 C27 C26 -179.6(2) . . . . ?
C23 C22 C27 C28 -175.5(2) . . . . ?
N2 C22 C27 C28 1.2(4) . . . . ?
C7 C12 C11 C10 0.0(4) . . . . ?
C13 C12 C11 C10 178.3(3) . . . . ?
C27 C22 C23 C24 -3.4(4) . . . . ?
N2 C22 C23 C24 179.9(2) . . . . ?
C27 C22 C23 C31 177.6(2) . . . . ?
N2 C22 C23 C31 0.8(4) . . . . ?
C7 C8 C9 C10 1.7(4) . . . . ?
C16 C8 C9 C10 -174.9(3) . . . . ?
C8 C9 C10 C11 -2.8(4) . . . . ?
C8 C9 C10 C19 174.9(2) . . . . ?
C12 C11 C10 C9 2.0(4) . . . . ?
C12 C11 C10 C19 -175.8(2) . . . . ?
C9 C10 C19 C20 6.2(4) . . . . ?
C11 C10 C19 C20 -176.1(3) . . . . ?
C9 C10 C19 C21 -119.0(3) . . . . ?
C11 C10 C19 C21 58.7(4) . . . . ?
C57 C52 C53 C54 -2.3(4) . . . . ?
P1 C52 C53 C54 -177.6(2) . . . . ?
C46 P1 C40 C45 -129.9(2) . . . . ?
C52 P1 C40 C45 -20.2(3) . . . . ?
NI1 P1 C40 C45 97.9(2) . . . . ?
C46 P1 C40 C41 53.2(3) . . . . ?
C52 P1 C40 C41 162.9(2) . . . . ?
NI1 P1 C40 C41 -79.0(2) . . . . ?
C24 C23 C31 C32 38.7(4) . . . . ?
C22 C23 C31 C32 -142.3(3) . . . . ?
C24 C23 C31 C33 -87.7(3) . . . . ?
C22 C23 C31 C33 91.3(3) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
N1 C5 C4 C3 1.4(3) . . . . ?
C7 C5 C4 C3 -161.9(3) . . . . ?
C55 C56 C57 C52 -0.1(4) . . . . ?
C53 C52 C57 C56 1.5(4) . . . . ?
P1 C52 C57 C56 176.7(2) . . . . ?
C51 C46 C47 C48 1.5(5) . . . . ?
P1 C46 C47 C48 -178.3(3) . . . . ?
C22 C27 C26 C25 -1.3(4) . . . . ?
C28 C27 C26 C25 177.9(3) . . . . ?
C27 C26 C25 C24 -1.5(4) . . . . ?
C34 C35 C36 C37 -0.3(5) . . . . ?
C52 C53 C54 C55 1.5(4) . . . . ?
C26 C25 C24 C23 1.9(4) . . . . ?
C22 C23 C24 C25 0.5(4) . . . . ?
C31 C23 C24 C25 179.5(2) . . . . ?
C35 C36 C37 C38 -0.5(5) . . . . ?
C11 C12 C13 C14 -83.1(3) . . . . ?
C7 C12 C13 C14 95.1(3) . . . . ?
C11 C12 C13 C15 40.2(3) . . . . ?
C7 C12 C13 C15 -141.6(3) . . . . ?
C51 C50 C49 C48 1.4(5) . . . . ?
C41 C40 C45 C44 0.5(4) . . . . ?
P1 C40 C45 C44 -176.4(2) . . . . ?
C26 C27 C28 C29 78.3(4) . . . . ?
C22 C27 C28 C29 -102.6(3) . . . . ?
C26 C27 C28 C30 -44.7(4) . . . . ?
C22 C27 C28 C30 134.5(3) . . . . ?
C50 C49 C48 C47 0.2(5) . . . . ?
C46 C47 C48 C49 -1.7(5) . . . . ?
C45 C40 C41 C42 -1.0(4) . . . . ?
P1 C40 C41 C42 176.0(2) . . . . ?
C36 C37 C38 C39 0.1(5) . . . . ?
C34 C39 C38 C37 1.1(5) . . . . ?
C40 C41 C42 C43 0.4(5) . . . . ?
C57 C56 C55 C54 -0.6(5) . . . . ?
C53 C54 C55 C56 -0.1(5) . . . . ?
C40 C45 C44 C43 0.5(5) . . . . ?
C45 C44 C43 C42 -1.1(5) . . . . ?
C41 C42 C43 C44 0.6(5) . . . . ?

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.069

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_h-m   'P -1'
_symmetry_int_tables_number      2
_chemical_absolute_configuration ?


####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1853550'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C47 H45 N2 Ni P'
_chemical_formula_sum            'C47 H45 N2 Ni P'
_chemical_melting_point          ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange

_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         727.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.4768(8)
_cell_length_b                   14.1372(11)
_cell_length_c                   23.4360(16)
_cell_angle_alpha                90
_cell_angle_beta                 93.967(3)
_cell_angle_gamma                90
_cell_volume                     3793.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9956
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      25.37
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_F_000             1536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.589
_shelx_estimated_absorpt_T_min   0.809
_shelx_estimated_absorpt_T_max   0.863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            97172
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.742
_diffrn_reflns_theta_max         25.726
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7232
_reflns_number_gt                5551
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0290P)²+1.8692P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7211
_refine_ls_number_parameters     464
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0725
_refine_ls_wR_factor_gt          0.0671
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.45350(2) 0.24480(2) 0.37385(2) 0.01479(7) Uani 1 1 d . . . . .
P1 P 0.27452(4) 0.19786(3) 0.36758(2) 0.01587(11) Uani 1 1 d . . . . .
N1 N 0.46231(12) 0.32155(10) 0.44217(6) 0.0164(3) Uani 1 1 d . . . . .
N2 N 0.62162(12) 0.22566(10) 0.39552(6) 0.0167(3) Uani 1 1 d . . . . .
C2 C 0.55693(15) 0.29395(13) 0.47799(7) 0.0188(4) Uani 1 1 d . . . . .
C3 C 0.55258(17) 0.33741(14) 0.53136(8) 0.0244(4) Uani 1 1 d . . . . .
H3 H 0.6063 0.3296 0.5637 0.029 Uiso 1 1 calc R U . . .
C4 C 0.45389(17) 0.39434(14) 0.52756(8) 0.0247(4) Uani 1 1 d . . . . .
H4 H 0.4268 0.4329 0.5571 0.030 Uiso 1 1 calc R U . . .
C5 C 0.40137(15) 0.38446(13) 0.47191(7) 0.0182(4) Uani 1 1 d . . . . .
C6 C 0.64275(15) 0.24404(13) 0.44998(7) 0.0184(4) Uani 1 1 d . . . . .
H6 H 0.7135 0.2244 0.4700 0.022 Uiso 1 1 calc R U . . .
C7 C 0.30612(15) 0.44100(13) 0.44501(8) 0.0195(4) Uani 1 1 d . . . . .
C8 C 0.21650(17) 0.47569(14) 0.47636(9) 0.0294(5) Uani 1 1 d . . . . .
H8 H 0.2146 0.4600 0.5157 0.035 Uiso 1 1 calc R U . . .
C9 C 0.13009(19) 0.53300(16) 0.45039(11) 0.0400(6) Uani 1 1 d . . . . .
H9 H 0.0686 0.5554 0.4719 0.048 Uiso 1 1 calc R U . . .
C10 C 0.13285(19) 0.55773(16) 0.39337(10) 0.0386(6) Uani 1 1 d . . . . .
H10 H 0.0738 0.5974 0.3759 0.046 Uiso 1 1 calc R U . . .
C11 C 0.22142(19) 0.52465(15) 0.36201(9) 0.0326(5) Uani 1 1 d . . . . .
H11 H 0.2238 0.5418 0.3229 0.039 Uiso 1 1 calc R U . . .
C12 C 0.30704(17) 0.46642(13) 0.38749(8) 0.0233(4) Uani 1 1 d . . . . .
H12 H 0.3674 0.4434 0.3654 0.028 Uiso 1 1 calc R U . . .
C13 C 0.71159(15) 0.18806(13) 0.36276(7) 0.0170(4) Uani 1 1 d . . . . .
C14 C 0.75636(15) 0.09675(13) 0.37184(8) 0.0195(4) Uani 1 1 d . . . . .
C15 C 0.83859(16) 0.06406(15) 0.33531(8) 0.0259(5) Uani 1 1 d . . . . .
H15 H 0.8710 0.0027 0.3411 0.031 Uiso 1 1 calc R U . . .
C16 C 0.87373(16) 0.11876(15) 0.29110(8) 0.0275(5) Uani 1 1 d . . . . .
H16 H 0.9282 0.0945 0.2661 0.033 Uiso 1 1 calc R U . . .
C17 C 0.82968(16) 0.20903(15) 0.28309(8) 0.0259(5) Uani 1 1 d . . . . .
H17 H 0.8551 0.2466 0.2527 0.031 Uiso 1 1 calc R U . . .
C18 C 0.74898(15) 0.24596(13) 0.31852(8) 0.0207(4) Uani 1 1 d . . . . .
C19 C 0.72251(17) 0.03168(13) 0.41971(8) 0.0248(4) Uani 1 1 d . . . . .
H19 H 0.6578 0.0626 0.4393 0.030 Uiso 1 1 calc R U . . .
C20 C 0.70355(17) 0.34669(14) 0.31129(8) 0.0268(5) Uani 1 1 d . . . . .
H20 H 0.6189 0.3458 0.3190 0.032 Uiso 1 1 calc R U . . .
C21 C 0.67845(18) -0.06405(14) 0.39704(10) 0.0338(5) Uani 1 1 d . . . . .
H21A H 0.6133 -0.0543 0.3684 0.051 Uiso 1 1 calc R U . . .
H21B H 0.6519 -0.1019 0.4287 0.051 Uiso 1 1 calc R U . . .
H21C H 0.7418 -0.0973 0.3795 0.051 Uiso 1 1 calc R U . . .
C22 C 0.82573(19) 0.01809(15) 0.46400(9) 0.0331(5) Uani 1 1 d . . . . .
H22A H 0.8904 -0.0123 0.4458 0.050 Uiso 1 1 calc R U . . .
H22B H 0.8016 -0.0219 0.4952 0.050 Uiso 1 1 calc R U . . .
H22C H 0.8512 0.0798 0.4793 0.050 Uiso 1 1 calc R U . . .
C23 C 0.7653(2) 0.41357(16) 0.35484(10) 0.0412(6) Uani 1 1 d . . . . .
H23A H 0.7549 0.3906 0.3936 0.062 Uiso 1 1 calc R U . . .
H23B H 0.7319 0.4771 0.3502 0.062 Uiso 1 1 calc R U . . .
H23C H 0.8488 0.4158 0.3486 0.062 Uiso 1 1 calc R U . . .
C24 C 0.7122(2) 0.38478(17) 0.25077(10) 0.0421(6) Uani 1 1 d . . . . .
H24A H 0.7945 0.3955 0.2439 0.063 Uiso 1 1 calc R U . . .
H24B H 0.6693 0.4446 0.2465 0.063 Uiso 1 1 calc R U . . .
H24C H 0.6785 0.3387 0.2231 0.063 Uiso 1 1 calc R U . . .
C25 C 0.46227(15) 0.19021(13) 0.30006(7) 0.0175(4) Uani 1 1 d . . . . .
C26 C 0.49983(16) 0.09981(14) 0.28733(8) 0.0223(4) Uani 1 1 d . . . . .
H26 H 0.5134 0.0553 0.3174 0.027 Uiso 1 1 calc R U . . .
C27 C 0.51810(18) 0.07271(15) 0.23177(8) 0.0312(5) Uani 1 1 d . . . . .
H27 H 0.5441 0.0104 0.2243 0.037 Uiso 1 1 calc R U . . .
C28 C 0.49854(19) 0.13595(17) 0.18754(9) 0.0363(5) Uani 1 1 d . . . . .
H28 H 0.5113 0.1175 0.1495 0.044 Uiso 1 1 calc R U . . .
C29 C 0.46038(18) 0.22620(16) 0.19861(8) 0.0323(5) Uani 1 1 d . . . . .
H29 H 0.4470 0.2701 0.1681 0.039 Uiso 1 1 calc R U . . .
C30 C 0.44140(16) 0.25308(14) 0.25428(8) 0.0237(4) Uani 1 1 d . . . . .
H30 H 0.4138 0.3150 0.2614 0.028 Uiso 1 1 calc R U . . .
C31 C 0.26808(16) 0.06966(13) 0.37926(7) 0.0180(4) Uani 1 1 d . . . . .
C32 C 0.16250(17) 0.02142(14) 0.37048(8) 0.0257(4) Uani 1 1 d . . . . .
H32 H 0.0947 0.0542 0.3558 0.031 Uiso 1 1 calc R U . . .
C33 C 0.15589(19) -0.07382(14) 0.38295(9) 0.0316(5) Uani 1 1 d . . . . .
H33 H 0.0837 -0.1062 0.3763 0.038 Uiso 1 1 calc R U . . .
C34 C 0.2529(2) -0.12234(15) 0.40489(9) 0.0333(5) Uani 1 1 d . . . . .
H34 H 0.2480 -0.1881 0.4128 0.040 Uiso 1 1 calc R U . . .
C35 C 0.35694(19) -0.07501(15) 0.41530(9) 0.0326(5) Uani 1 1 d . . . . .
H35 H 0.4236 -0.1080 0.4312 0.039 Uiso 1 1 calc R U . . .
C36 C 0.36513(17) 0.02075(14) 0.40267(8) 0.0246(4) Uani 1 1 d . . . . .
H36 H 0.4373 0.0529 0.4101 0.029 Uiso 1 1 calc R U . . .
C37 C 0.19119(15) 0.21804(13) 0.29957(7) 0.0177(4) Uani 1 1 d . . . . .
C38 C 0.18846(16) 0.15082(14) 0.25627(8) 0.0220(4) Uani 1 1 d . . . . .
H38 H 0.2218 0.0901 0.2636 0.026 Uiso 1 1 calc R U . . .
C39 C 0.13748(17) 0.17170(15) 0.20248(8) 0.0270(5) Uani 1 1 d . . . . .
H39 H 0.1363 0.1255 0.1730 0.032 Uiso 1 1 calc R U . . .
C40 C 0.08838(17) 0.25935(15) 0.19150(8) 0.0294(5) Uani 1 1 d . . . . .
H40 H 0.0531 0.2734 0.1546 0.035 Uiso 1 1 calc R U . . .
C41 C 0.09056(17) 0.32677(15) 0.23425(8) 0.0276(5) Uani 1 1 d . . . . .
H41 H 0.0562 0.3870 0.2267 0.033 Uiso 1 1 calc R U . . .
C42 C 0.14259(15) 0.30695(13) 0.28793(8) 0.0215(4) Uani 1 1 d . . . . .
H42 H 0.1452 0.3540 0.3169 0.026 Uiso 1 1 calc R U . . .
C43 C 0.17749(15) 0.23212(12) 0.42308(8) 0.0179(4) Uani 1 1 d . . . . .
C44 C 0.22333(17) 0.22718(13) 0.47953(8) 0.0209(4) Uani 1 1 d . . . . .
H44 H 0.3035 0.2123 0.4875 0.025 Uiso 1 1 calc R U . . .
C45 C 0.15319(18) 0.24379(13) 0.52434(8) 0.0273(5) Uani 1 1 d . . . . .
H45 H 0.1855 0.2405 0.5627 0.033 Uiso 1 1 calc R U . . .
C46 C 0.03661(19) 0.26501(14) 0.51317(9) 0.0314(5) Uani 1 1 d . . . . .
H46 H -0.0115 0.2765 0.5438 0.038 Uiso 1 1 calc R U . . .
C47 C -0.01018(18) 0.26952(15) 0.45740(9) 0.0311(5) Uani 1 1 d . . . . .
H47 H -0.0906 0.2840 0.4499 0.037 Uiso 1 1 calc R U . . .
C48 C 0.05899(16) 0.25310(14) 0.41229(8) 0.0248(4) Uani 1 1 d . . . . .
H48 H 0.0259 0.2561 0.3740 0.030 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 C25 1.9029(17) . ?
Ni1 N1 1.9310(14) . ?
Ni1 N2 1.9795(14) . ?
Ni1 P1 2.1540(5) . ?
P1 C37 1.8235(18) . ?
P1 C43 1.8350(18) . ?
P1 C31 1.8352(19) . ?
N1 C5 1.354(2) . ?
N1 C2 1.382(2) . ?
N2 C6 1.309(2) . ?
N2 C13 1.431(2) . ?
C2 C3 1.398(2) . ?
C2 C6 1.410(3) . ?
C3 C4 1.387(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.405(2) . ?
C4 H4 0.9500 . ?
C5 C7 1.462(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(3) . ?
C7 C12 1.396(3) . ?
C8 C9 1.388(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.400(3) . ?
C13 C18 1.411(3) . ?
C14 C15 1.396(3) . ?
C14 C19 1.522(3) . ?
C15 C16 1.376(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 C20 1.522(3) . ?
C19 C21 1.527(3) . ?
C19 C22 1.532(3) . ?
C19 H19 1.0000 . ?
C20 C24 1.527(3) . ?
C20 C23 1.529(3) . ?
C20 H20 1.0000 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.388(3) . ?
C25 C30 1.401(3) . ?
C26 C27 1.387(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.375(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.379(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.390(3) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C36 1.391(3) . ?
C31 C32 1.393(3) . ?
C32 C33 1.381(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.376(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.376(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.390(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C38 1.389(3) . ?
C37 C42 1.395(3) . ?
C38 C39 1.384(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.378(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.382(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.383(3) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 C44 1.391(3) . ?
C43 C48 1.398(3) . ?
C44 C45 1.387(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.379(3) . ?
C45 H45 0.9500 . ?
C46 C47 1.380(3) . ?
C46 H46 0.9500 . ?
C47 C48 1.385(3) . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C25 Ni1 N1 168.09(7) . . ?
C25 Ni1 N2 93.77(7) . . ?
N1 Ni1 N2 82.53(6) . . ?
C25 Ni1 P1 85.59(5) . . ?
N1 Ni1 P1 102.99(4) . . ?
N2 Ni1 P1 152.06(5) . . ?
C37 P1 C43 105.72(8) . . ?
C37 P1 C31 105.12(8) . . ?
C43 P1 C31 97.02(8) . . ?
C37 P1 Ni1 116.84(6) . . ?
C43 P1 Ni1 119.53(6) . . ?
C31 P1 Ni1 110.01(6) . . ?
C5 N1 C2 106.56(14) . . ?
C5 N1 Ni1 142.81(12) . . ?
C2 N1 Ni1 109.80(11) . . ?
C6 N2 C13 120.34(14) . . ?
C6 N2 Ni1 109.55(11) . . ?
C13 N2 Ni1 129.78(11) . . ?
N1 C2 C3 110.13(16) . . ?
N1 C2 C6 113.80(15) . . ?
C3 C2 C6 134.91(17) . . ?
C4 C3 C2 106.09(16) . . ?
C4 C3 H3 127.0 . . ?
C2 C3 H3 127.0 . . ?
C3 C4 C5 107.32(16) . . ?
C3 C4 H4 126.3 . . ?
C5 C4 H4 126.3 . . ?
N1 C5 C4 109.83(16) . . ?
N1 C5 C7 122.33(15) . . ?
C4 C5 C7 127.30(16) . . ?
N2 C6 C2 117.71(16) . . ?
N2 C6 H6 121.1 . . ?
C2 C6 H6 121.1 . . ?
C8 C7 C12 118.27(17) . . ?
C8 C7 C5 121.48(17) . . ?
C12 C7 C5 120.13(16) . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 121.12(18) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
C14 C13 C18 121.30(16) . . ?
C14 C13 N2 122.12(16) . . ?
C18 C13 N2 116.50(16) . . ?
C15 C14 C13 117.94(17) . . ?
C15 C14 C19 118.02(17) . . ?
C13 C14 C19 124.03(16) . . ?
C16 C15 C14 121.45(19) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 119.90(18) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 121.30(18) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C17 C18 C13 118.09(18) . . ?
C17 C18 C20 121.54(17) . . ?
C13 C18 C20 120.35(16) . . ?
C14 C19 C21 111.99(16) . . ?
C14 C19 C22 110.51(16) . . ?
C21 C19 C22 110.28(16) . . ?
C14 C19 H19 108.0 . . ?
C21 C19 H19 108.0 . . ?
C22 C19 H19 108.0 . . ?
C18 C20 C24 112.92(17) . . ?
C18 C20 C23 111.40(16) . . ?
C24 C20 C23 110.17(18) . . ?
C18 C20 H20 107.4 . . ?
C24 C20 H20 107.4 . . ?
C23 C20 H20 107.4 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C30 117.31(17) . . ?
C26 C25 Ni1 127.27(14) . . ?
C30 C25 Ni1 114.94(14) . . ?
C27 C26 C25 121.70(18) . . ?
C27 C26 H26 119.1 . . ?
C25 C26 H26 119.1 . . ?
C28 C27 C26 120.0(2) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C29 119.80(19) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 H28 120.1 . . ?
C28 C29 C30 120.10(19) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C29 C30 C25 121.04(19) . . ?
C29 C30 H30 119.5 . . ?
C25 C30 H30 119.5 . . ?
C36 C31 C32 118.65(17) . . ?
C36 C31 P1 120.69(14) . . ?
C32 C31 P1 120.33(14) . . ?
C33 C32 C31 120.39(19) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C34 C33 C32 120.7(2) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C35 C34 C33 119.57(19) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C34 C35 C36 120.42(19) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C35 C36 C31 120.25(19) . . ?
C35 C36 H36 119.9 . . ?
C31 C36 H36 119.9 . . ?
C38 C37 C42 119.02(16) . . ?
C38 C37 P1 121.03(14) . . ?
C42 C37 P1 119.38(14) . . ?
C39 C38 C37 120.41(18) . . ?
C39 C38 H38 119.8 . . ?
C37 C38 H38 119.8 . . ?
C40 C39 C38 120.22(18) . . ?
C40 C39 H39 119.9 . . ?
C38 C39 H39 119.9 . . ?
C39 C40 C41 119.88(18) . . ?
C39 C40 H40 120.1 . . ?
C41 C40 H40 120.1 . . ?
C40 C41 C42 120.31(19) . . ?
C40 C41 H41 119.8 . . ?
C42 C41 H41 119.8 . . ?
C41 C42 C37 120.14(18) . . ?
C41 C42 H42 119.9 . . ?
C37 C42 H42 119.9 . . ?
C44 C43 C48 118.80(17) . . ?
C44 C43 P1 116.92(13) . . ?
C48 C43 P1 123.94(14) . . ?
C45 C44 C43 120.70(18) . . ?
C45 C44 H44 119.7 . . ?
C43 C44 H44 119.7 . . ?
C46 C45 C44 119.99(19) . . ?
C46 C45 H45 120.0 . . ?
C44 C45 H45 120.0 . . ?
C45 C46 C47 119.93(18) . . ?
C45 C46 H46 120.0 . . ?
C47 C46 H46 120.0 . . ?
C46 C47 C48 120.61(19) . . ?
C46 C47 H47 119.7 . . ?
C48 C47 H47 119.7 . . ?
C47 C48 C43 119.97(18) . . ?
C47 C48 H48 120.0 . . ?
C43 C48 H48 120.0 . . ?

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
C5 N1 C2 C3 2.2(2) . . . . ?
Ni1 N1 C2 C3 -169.82(13) . . . . ?
C5 N1 C2 C6 -167.31(15) . . . . ?
Ni1 N1 C2 C6 20.64(19) . . . . ?
N1 C2 C3 C4 -1.1(2) . . . . ?
C6 C2 C3 C4 165.3(2) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C2 N1 C5 C4 -2.5(2) . . . . ?
Ni1 N1 C5 C4 165.11(16) . . . . ?
C2 N1 C5 C7 169.68(16) . . . . ?
Ni1 N1 C5 C7 -22.7(3) . . . . ?
C3 C4 C5 N1 1.8(2) . . . . ?
C3 C4 C5 C7 -169.85(18) . . . . ?
C13 N2 C6 C2 170.64(16) . . . . ?
Ni1 N2 C6 C2 -15.3(2) . . . . ?
N1 C2 C6 N2 -3.3(2) . . . . ?
C3 C2 C6 N2 -169.3(2) . . . . ?
N1 C5 C7 C8 154.32(18) . . . . ?
C4 C5 C7 C8 -35.0(3) . . . . ?
N1 C5 C7 C12 -29.7(3) . . . . ?
C4 C5 C7 C12 141.0(2) . . . . ?
C12 C7 C8 C9 0.8(3) . . . . ?
C5 C7 C8 C9 176.90(19) . . . . ?
C7 C8 C9 C10 -1.1(3) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C10 C11 C12 C7 -0.6(3) . . . . ?
C8 C7 C12 C11 0.1(3) . . . . ?
C5 C7 C12 C11 -176.09(18) . . . . ?
C6 N2 C13 C14 67.9(2) . . . . ?
Ni1 N2 C13 C14 -104.76(18) . . . . ?
C6 N2 C13 C18 -115.36(19) . . . . ?
Ni1 N2 C13 C18 72.0(2) . . . . ?
C18 C13 C14 C15 -0.7(3) . . . . ?
N2 C13 C14 C15 175.93(16) . . . . ?
C18 C13 C14 C19 178.20(17) . . . . ?
N2 C13 C14 C19 -5.2(3) . . . . ?
C13 C14 C15 C16 -1.0(3) . . . . ?
C19 C14 C15 C16 -179.93(17) . . . . ?
C14 C15 C16 C17 1.7(3) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C16 C17 C18 C13 -0.9(3) . . . . ?
C16 C17 C18 C20 177.68(17) . . . . ?
C14 C13 C18 C17 1.6(3) . . . . ?
N2 C13 C18 C17 -175.20(16) . . . . ?
C14 C13 C18 C20 -176.99(16) . . . . ?
N2 C13 C18 C20 6.2(2) . . . . ?
C15 C14 C19 C21 -55.7(2) . . . . ?
C13 C14 C19 C21 125.41(19) . . . . ?
C15 C14 C19 C22 67.6(2) . . . . ?
C13 C14 C19 C22 -111.2(2) . . . . ?
C17 C18 C20 C24 24.2(3) . . . . ?
C13 C18 C20 C24 -157.29(17) . . . . ?
C17 C18 C20 C23 -100.4(2) . . . . ?
C13 C18 C20 C23 78.1(2) . . . . ?
C30 C25 C26 C27 1.1(3) . . . . ?
Ni1 C25 C26 C27 -170.58(15) . . . . ?
C25 C26 C27 C28 -0.3(3) . . . . ?
C26 C27 C28 C29 -0.2(3) . . . . ?
C27 C28 C29 C30 -0.2(3) . . . . ?
C28 C29 C30 C25 1.1(3) . . . . ?
C26 C25 C30 C29 -1.5(3) . . . . ?
Ni1 C25 C30 C29 171.21(15) . . . . ?
C37 P1 C31 C36 141.15(15) . . . . ?
C43 P1 C31 C36 -110.42(15) . . . . ?
Ni1 P1 C31 C36 14.56(16) . . . . ?
C37 P1 C31 C32 -45.66(16) . . . . ?
C43 P1 C31 C32 62.77(16) . . . . ?
Ni1 P1 C31 C32 -172.25(13) . . . . ?
C36 C31 C32 C33 -2.3(3) . . . . ?
P1 C31 C32 C33 -175.59(15) . . . . ?
C31 C32 C33 C34 0.8(3) . . . . ?
C32 C33 C34 C35 1.0(3) . . . . ?
C33 C34 C35 C36 -1.4(3) . . . . ?
C34 C35 C36 C31 -0.1(3) . . . . ?
C32 C31 C36 C35 1.9(3) . . . . ?
P1 C31 C36 C35 175.21(15) . . . . ?
C43 P1 C37 C38 -134.17(15) . . . . ?
C31 P1 C37 C38 -32.19(17) . . . . ?
Ni1 P1 C37 C38 90.08(15) . . . . ?
C43 P1 C37 C42 54.57(16) . . . . ?
C31 P1 C37 C42 156.55(14) . . . . ?
Ni1 P1 C37 C42 -81.18(15) . . . . ?
C42 C37 C38 C39 -0.4(3) . . . . ?
P1 C37 C38 C39 -171.74(15) . . . . ?
C37 C38 C39 C40 -0.3(3) . . . . ?
C38 C39 C40 C41 0.3(3) . . . . ?
C39 C40 C41 C42 0.5(3) . . . . ?
C40 C41 C42 C37 -1.3(3) . . . . ?
C38 C37 C42 C41 1.2(3) . . . . ?
P1 C37 C42 C41 172.68(14) . . . . ?
C37 P1 C43 C44 -177.17(14) . . . . ?
C31 P1 C43 C44 74.91(15) . . . . ?
Ni1 P1 C43 C44 -42.86(16) . . . . ?
C37 P1 C43 C48 9.57(18) . . . . ?
C31 P1 C43 C48 -98.35(17) . . . . ?
Ni1 P1 C43 C48 143.88(14) . . . . ?
C48 C43 C44 C45 -0.7(3) . . . . ?
P1 C43 C44 C45 -174.34(14) . . . . ?
C43 C44 C45 C46 0.3(3) . . . . ?
C44 C45 C46 C47 0.1(3) . . . . ?
C45 C46 C47 C48 -0.1(3) . . . . ?
C46 C47 C48 C43 -0.3(3) . . . . ?
C44 C43 C48 C47 0.7(3) . . . . ?
P1 C43 C48 C47 173.84(15) . . . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.051

_shelxl_version_number           2014-3

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1853551'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C41 H28 F5 N2 Ni P'
_chemical_formula_sum            'C41 H28 F5 N2 Ni P'
_chemical_melting_point          ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         733.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_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.
;

_cell_length_a                   13.1214(7)
_cell_length_b                   8.8622(4)
_cell_length_c                   31.0382(15)
_cell_angle_alpha                90
_cell_angle_beta                 101.361(2)
_cell_angle_gamma                90
_cell_volume                     3538.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2735
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      21.87
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.652
_shelx_estimated_absorpt_T_min   0.881
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  0.903
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29088
_diffrn_reflns_av_unetI/netI     0.0821
_diffrn_reflns_av_R_equivalents  0.0842
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.660
_diffrn_reflns_theta_max         25.767
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6736
_reflns_number_gt                4557
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0498P)²+0.4870P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6736
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1175
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.21612(3) 0.17868(5) 0.34366(2) 0.01746(13) Uani 1 1 d . . . . .
P1 P 0.31602(7) 0.09641(9) 0.40308(3) 0.0181(2) Uani 1 1 d . . . . .
F1 F -0.02876(15) 0.1130(2) 0.26860(7) 0.0314(5) Uani 1 1 d . . . . .
F2 F -0.23009(15) 0.1637(2) 0.26830(7) 0.0397(6) Uani 1 1 d . . . . .
F3 F -0.29164(16) 0.4296(2) 0.29843(8) 0.0433(6) Uani 1 1 d . . . . .
F4 F -0.14864(18) 0.6470(2) 0.32647(8) 0.0516(7) Uani 1 1 d . . . . .
F5 F 0.05291(16) 0.5980(2) 0.32756(8) 0.0411(6) Uani 1 1 d . . . . .
N1 N 0.3176(2) 0.2242(3) 0.30554(8) 0.0178(6) Uani 1 1 d . . . . .
N2 N 0.1258(2) 0.3159(3) 0.30218(8) 0.0205(6) Uani 1 1 d . . . . .
C2 C 0.2864(3) 0.3596(4) 0.28447(10) 0.0214(8) Uani 1 1 d . . . . .
C3 C 0.3634(3) 0.4183(4) 0.26386(11) 0.0279(9) Uani 1 1 d . . . . .
H3 H 0.360680 0.509707 0.247680 0.034 Uiso 1 1 calc R U . . .
C4 C 0.4444(3) 0.3157(4) 0.27193(11) 0.0258(8) Uani 1 1 d . . . . .
H4 H 0.508512 0.323369 0.262223 0.031 Uiso 1 1 calc R U . . .
C5 C 0.4143(3) 0.1972(4) 0.29727(10) 0.0203(8) Uani 1 1 d . . . . .
C6 C 0.1836(3) 0.4044(4) 0.28326(10) 0.0213(8) Uani 1 1 d . . . . .
H6 H 0.156903 0.495472 0.269258 0.026 Uiso 1 1 calc R U . . .
C7 C 0.4746(3) 0.0605(4) 0.31049(10) 0.0205(8) Uani 1 1 d . . . . .
C8 C 0.5825(3) 0.0625(4) 0.31493(11) 0.0272(8) Uani 1 1 d . . . . .
H8 H 0.616770 0.154514 0.311161 0.033 Uiso 1 1 calc R U . . .
C9 C 0.6403(3) -0.0687(4) 0.32480(12) 0.0350(10) Uani 1 1 d . . . . .
H9 H 0.713634 -0.065897 0.327443 0.042 Uiso 1 1 calc R U . . .
C10 C 0.5917(3) -0.2031(4) 0.33079(12) 0.0342(9) Uani 1 1 d . . . . .
H10 H 0.631522 -0.292549 0.337597 0.041 Uiso 1 1 calc R U . . .
C11 C 0.4847(3) -0.2068(4) 0.32682(11) 0.0326(9) Uani 1 1 d . . . . .
H11 H 0.450958 -0.298945 0.331023 0.039 Uiso 1 1 calc R U . . .
C12 C 0.4273(3) -0.0767(4) 0.31674(10) 0.0244(8) Uani 1 1 d . . . . .
H12 H 0.353928 -0.080476 0.313997 0.029 Uiso 1 1 calc R U . . .
C13 C 0.0200(2) 0.3521(4) 0.29862(10) 0.0201(8) Uani 1 1 d . . . . .
C14 C -0.0562(3) 0.2458(4) 0.28339(10) 0.0206(8) Uani 1 1 d . . . . .
C15 C -0.1591(3) 0.2703(4) 0.28294(11) 0.0252(8) Uani 1 1 d . . . . .
C16 C -0.1910(3) 0.4050(4) 0.29769(12) 0.0299(9) Uani 1 1 d . . . . .
C17 C -0.1181(3) 0.5152(4) 0.31151(12) 0.0315(9) Uani 1 1 d . . . . .
C18 C -0.0154(3) 0.4884(4) 0.31162(12) 0.0268(8) Uani 1 1 d . . . . .
C19 C 0.1019(2) 0.1401(4) 0.37073(11) 0.0207(8) Uani 1 1 d . . . . .
C20 C 0.0468(3) 0.0042(4) 0.36243(12) 0.0284(9) Uani 1 1 d . . . . .
H20 H 0.074449 -0.075565 0.347804 0.034 Uiso 1 1 calc R U . . .
C21 C -0.0474(3) -0.0150(5) 0.37531(15) 0.0436(11) Uani 1 1 d . . . . .
H21 H -0.084087 -0.107501 0.369328 0.052 Uiso 1 1 calc R U . . .
C22 C -0.0885(3) 0.0991(5) 0.39677(15) 0.0490(12) Uani 1 1 d . . . . .
H22 H -0.153427 0.085562 0.405410 0.059 Uiso 1 1 calc R U . . .
C23 C -0.0352(3) 0.2324(5) 0.40562(13) 0.0418(11) Uani 1 1 d . . . . .
H23 H -0.062934 0.311018 0.420671 0.050 Uiso 1 1 calc R U . . .
C24 C 0.0584(3) 0.2521(4) 0.39266(11) 0.0282(9) Uani 1 1 d . . . . .
H24 H 0.094247 0.345129 0.398896 0.034 Uiso 1 1 calc R U . . .
C25 C 0.3180(2) -0.1072(4) 0.41219(10) 0.0186(7) Uani 1 1 d . . . . .
C26 C 0.3615(3) -0.1668(4) 0.45326(11) 0.0255(8) Uani 1 1 d . . . . .
H26 H 0.393677 -0.101703 0.476277 0.031 Uiso 1 1 calc R U . . .
C27 C 0.3578(3) -0.3200(4) 0.46053(12) 0.0314(9) Uani 1 1 d . . . . .
H27 H 0.386817 -0.359925 0.488689 0.038 Uiso 1 1 calc R U . . .
C28 C 0.3125(3) -0.4154(4) 0.42725(12) 0.0312(9) Uani 1 1 d . . . . .
H28 H 0.309830 -0.520851 0.432484 0.037 Uiso 1 1 calc R U . . .
C29 C 0.2709(3) -0.3577(4) 0.38631(12) 0.0287(9) Uani 1 1 d . . . . .
H29 H 0.241437 -0.423748 0.363069 0.034 Uiso 1 1 calc R U . . .
C30 C 0.2721(3) -0.2043(4) 0.37903(11) 0.0229(8) Uani 1 1 d . . . . .
H30 H 0.241225 -0.164879 0.351044 0.027 Uiso 1 1 calc R U . . .
C31 C 0.2916(3) 0.1596(4) 0.45681(11) 0.0224(8) Uani 1 1 d . . . . .
C32 C 0.2038(3) 0.1072(4) 0.47121(11) 0.0304(9) Uani 1 1 d . . . . .
H32 H 0.156436 0.042003 0.452976 0.036 Uiso 1 1 calc R U . . .
C33 C 0.1854(3) 0.1496(5) 0.51191(12) 0.0414(11) Uani 1 1 d . . . . .
H33 H 0.125136 0.113693 0.521356 0.050 Uiso 1 1 calc R U . . .
C34 C 0.2540(4) 0.2438(5) 0.53894(13) 0.0452(11) Uani 1 1 d . . . . .
H34 H 0.240548 0.273866 0.566656 0.054 Uiso 1 1 calc R U . . .
C35 C 0.3424(3) 0.2940(4) 0.52537(12) 0.0398(10) Uani 1 1 d . . . . .
H35 H 0.390646 0.356847 0.544030 0.048 Uiso 1 1 calc R U . . .
C36 C 0.3604(3) 0.2521(4) 0.48430(11) 0.0297(9) Uani 1 1 d . . . . .
H36 H 0.420962 0.287525 0.475023 0.036 Uiso 1 1 calc R U . . .
C37 C 0.4501(3) 0.1590(4) 0.40670(10) 0.0209(8) Uani 1 1 d . . . . .
C38 C 0.5363(3) 0.0746(4) 0.42473(11) 0.0256(8) Uani 1 1 d . . . . .
H38 H 0.527769 -0.025601 0.434321 0.031 Uiso 1 1 calc R U . . .
C39 C 0.6361(3) 0.1355(4) 0.42900(12) 0.0337(10) Uani 1 1 d . . . . .
H39 H 0.694963 0.076585 0.441517 0.040 Uiso 1 1 calc R U . . .
C40 C 0.6494(3) 0.2796(4) 0.41524(12) 0.0332(9) Uani 1 1 d . . . . .
H40 H 0.717279 0.320937 0.418532 0.040 Uiso 1 1 calc R U . . .
C41 C 0.5641(3) 0.3647(4) 0.39659(11) 0.0308(9) Uani 1 1 d . . . . .
H41 H 0.573331 0.464164 0.386606 0.037 Uiso 1 1 calc R U . . .
C42 C 0.4654(3) 0.3058(4) 0.39241(10) 0.0226(8) Uani 1 1 d . . . . .
H42 H 0.407014 0.365435 0.379684 0.027 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 C19 1.888(3) . ?
Ni1 N2 1.985(3) . ?
Ni1 N1 1.989(3) . ?
Ni1 P1 2.1678(9) . ?
P1 C25 1.826(3) . ?
P1 C37 1.827(3) . ?
P1 C31 1.846(3) . ?
F1 C14 1.338(4) . ?
F2 C15 1.342(4) . ?
F3 C16 1.343(4) . ?
F4 C17 1.346(4) . ?
F5 C18 1.348(4) . ?
N1 C5 1.364(4) . ?
N1 C2 1.389(4) . ?
N2 C6 1.308(4) . ?
N2 C13 1.408(4) . ?
C2 C6 1.399(4) . ?
C2 C3 1.399(5) . ?
C3 C4 1.384(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.414(4) . ?
C4 H4 0.9500 . ?
C5 C7 1.461(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.395(5) . ?
C7 C12 1.396(5) . ?
C8 C9 1.389(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.380(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.383(5) . ?
C13 C14 1.387(5) . ?
C14 C15 1.365(5) . ?
C15 C16 1.373(5) . ?
C16 C17 1.375(5) . ?
C17 C18 1.368(5) . ?
C19 C24 1.389(5) . ?
C19 C20 1.402(5) . ?
C20 C21 1.382(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.378(6) . ?
C21 H21 0.9500 . ?
C22 C23 1.373(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.377(5) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C30 1.385(5) . ?
C25 C26 1.394(4) . ?
C26 C27 1.379(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.376(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.379(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.379(5) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C36 1.382(5) . ?
C31 C32 1.394(5) . ?
C32 C33 1.384(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.384(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.382(6) . ?
C34 H34 0.9500 . ?
C35 C36 1.392(5) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C38 1.379(5) . ?
C37 C42 1.402(4) . ?
C38 C39 1.399(5) . ?
C38 H38 0.9500 . ?
C39 C40 1.368(5) . ?
C39 H39 0.9500 . ?
C40 C41 1.379(5) . ?
C40 H40 0.9500 . ?
C41 C42 1.378(5) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 Ni1 N2 88.55(12) . . ?
C19 Ni1 N1 169.89(12) . . ?
N2 Ni1 N1 82.77(11) . . ?
C19 Ni1 P1 87.73(10) . . ?
N2 Ni1 P1 160.32(8) . . ?
N1 Ni1 P1 102.17(8) . . ?
C25 P1 C37 107.85(15) . . ?
C25 P1 C31 99.20(14) . . ?
C37 P1 C31 100.88(15) . . ?
C25 P1 Ni1 116.86(11) . . ?
C37 P1 Ni1 111.34(11) . . ?
C31 P1 Ni1 118.88(11) . . ?
C5 N1 C2 105.2(3) . . ?
C5 N1 Ni1 146.4(2) . . ?
C2 N1 Ni1 106.6(2) . . ?
C6 N2 C13 118.6(3) . . ?
C6 N2 Ni1 109.5(2) . . ?
C13 N2 Ni1 130.1(2) . . ?
N1 C2 C6 116.8(3) . . ?
N1 C2 C3 111.3(3) . . ?
C6 C2 C3 131.4(3) . . ?
C4 C3 C2 105.7(3) . . ?
C4 C3 H3 127.1 . . ?
C2 C3 H3 127.1 . . ?
C3 C4 C5 107.4(3) . . ?
C3 C4 H4 126.3 . . ?
C5 C4 H4 126.3 . . ?
N1 C5 C4 110.3(3) . . ?
N1 C5 C7 124.4(3) . . ?
C4 C5 C7 125.2(3) . . ?
N2 C6 C2 117.3(3) . . ?
N2 C6 H6 121.3 . . ?
C2 C6 H6 121.3 . . ?
C8 C7 C12 117.9(3) . . ?
C8 C7 C5 120.0(3) . . ?
C12 C7 C5 122.0(3) . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 119.7(4) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 119.9(4) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 121.4(3) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
C18 C13 C14 115.6(3) . . ?
C18 C13 N2 123.9(3) . . ?
C14 C13 N2 120.4(3) . . ?
F1 C14 C15 117.9(3) . . ?
F1 C14 C13 119.4(3) . . ?
C15 C14 C13 122.7(3) . . ?
F2 C15 C14 120.8(3) . . ?
F2 C15 C16 119.2(3) . . ?
C14 C15 C16 120.1(3) . . ?
F3 C16 C15 120.8(3) . . ?
F3 C16 C17 120.3(3) . . ?
C15 C16 C17 118.9(3) . . ?
F4 C17 C18 120.6(3) . . ?
F4 C17 C16 119.2(3) . . ?
C18 C17 C16 120.1(3) . . ?
F5 C18 C17 117.4(3) . . ?
F5 C18 C13 120.0(3) . . ?
C17 C18 C13 122.6(3) . . ?
C24 C19 C20 117.2(3) . . ?
C24 C19 Ni1 121.8(3) . . ?
C20 C19 Ni1 120.0(3) . . ?
C21 C20 C19 120.7(4) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C20 120.4(4) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 119.8(4) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 119.9(4) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C19 121.9(4) . . ?
C23 C24 H24 119.0 . . ?
C19 C24 H24 119.0 . . ?
C30 C25 C26 119.0(3) . . ?
C30 C25 P1 120.5(2) . . ?
C26 C25 P1 120.4(3) . . ?
C27 C26 C25 120.1(3) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C28 C27 C26 120.4(3) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 119.9(3) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 H28 120.1 . . ?
C28 C29 C30 120.1(3) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C29 C30 C25 120.5(3) . . ?
C29 C30 H30 119.7 . . ?
C25 C30 H30 119.7 . . ?
C36 C31 C32 118.7(3) . . ?
C36 C31 P1 121.9(3) . . ?
C32 C31 P1 119.3(3) . . ?
C33 C32 C31 120.4(4) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C34 C33 C32 120.4(4) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C35 C34 C33 119.6(4) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C34 C35 C36 119.8(4) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
C31 C36 C35 121.0(4) . . ?
C31 C36 H36 119.5 . . ?
C35 C36 H36 119.5 . . ?
C38 C37 C42 118.3(3) . . ?
C38 C37 P1 124.3(3) . . ?
C42 C37 P1 117.3(2) . . ?
C37 C38 C39 120.4(3) . . ?
C37 C38 H38 119.8 . . ?
C39 C38 H38 119.8 . . ?
C40 C39 C38 120.4(4) . . ?
C40 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?
C39 C40 C41 119.9(4) . . ?
C39 C40 H40 120.1 . . ?
C41 C40 H40 120.1 . . ?
C42 C41 C40 120.2(4) . . ?
C42 C41 H41 119.9 . . ?
C40 C41 H41 119.9 . . ?
C41 C42 C37 120.8(3) . . ?
C41 C42 H42 119.6 . . ?
C37 C42 H42 119.6 . . ?

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
C5 N1 C2 C6 172.4(3) . . . . ?
Ni1 N1 C2 C6 -18.8(3) . . . . ?
C5 N1 C2 C3 -1.1(4) . . . . ?
Ni1 N1 C2 C3 167.8(2) . . . . ?
N1 C2 C3 C4 0.7(4) . . . . ?
C6 C2 C3 C4 -171.5(3) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C2 N1 C5 C4 1.0(3) . . . . ?
Ni1 N1 C5 C4 -159.4(3) . . . . ?
C2 N1 C5 C7 -175.4(3) . . . . ?
Ni1 N1 C5 C7 24.2(6) . . . . ?
C3 C4 C5 N1 -0.7(4) . . . . ?
C3 C4 C5 C7 175.7(3) . . . . ?
C13 N2 C6 C2 -175.2(3) . . . . ?
Ni1 N2 C6 C2 18.7(4) . . . . ?
N1 C2 C6 N2 0.3(4) . . . . ?
C3 C2 C6 N2 172.2(3) . . . . ?
N1 C5 C7 C8 -157.4(3) . . . . ?
C4 C5 C7 C8 26.7(5) . . . . ?
N1 C5 C7 C12 26.1(5) . . . . ?
C4 C5 C7 C12 -149.8(3) . . . . ?
C12 C7 C8 C9 0.7(5) . . . . ?
C5 C7 C8 C9 -176.0(3) . . . . ?
C7 C8 C9 C10 -0.6(5) . . . . ?
C8 C9 C10 C11 0.1(6) . . . . ?
C9 C10 C11 C12 0.3(5) . . . . ?
C10 C11 C12 C7 -0.2(5) . . . . ?
C8 C7 C12 C11 -0.3(5) . . . . ?
C5 C7 C12 C11 176.3(3) . . . . ?
C6 N2 C13 C18 -56.4(4) . . . . ?
Ni1 N2 C13 C18 106.3(4) . . . . ?
C6 N2 C13 C14 126.9(3) . . . . ?
Ni1 N2 C13 C14 -70.3(4) . . . . ?
C18 C13 C14 F1 177.5(3) . . . . ?
N2 C13 C14 F1 -5.6(5) . . . . ?
C18 C13 C14 C15 -2.9(5) . . . . ?
N2 C13 C14 C15 174.1(3) . . . . ?
F1 C14 C15 F2 0.3(5) . . . . ?
C13 C14 C15 F2 -179.3(3) . . . . ?
F1 C14 C15 C16 -179.8(3) . . . . ?
C13 C14 C15 C16 0.5(5) . . . . ?
F2 C15 C16 F3 1.4(5) . . . . ?
C14 C15 C16 F3 -178.4(3) . . . . ?
F2 C15 C16 C17 -178.2(3) . . . . ?
C14 C15 C16 C17 1.9(5) . . . . ?
F3 C16 C17 F4 1.1(5) . . . . ?
C15 C16 C17 F4 -179.3(3) . . . . ?
F3 C16 C17 C18 178.5(3) . . . . ?
C15 C16 C17 C18 -1.9(6) . . . . ?
F4 C17 C18 F5 0.6(5) . . . . ?
C16 C17 C18 F5 -176.8(3) . . . . ?
F4 C17 C18 C13 176.7(3) . . . . ?
C16 C17 C18 C13 -0.7(6) . . . . ?
C14 C13 C18 F5 179.0(3) . . . . ?
N2 C13 C18 F5 2.2(5) . . . . ?
C14 C13 C18 C17 2.9(5) . . . . ?
N2 C13 C18 C17 -173.9(3) . . . . ?
N2 Ni1 C19 C24 -65.1(3) . . . . ?
N1 Ni1 C19 C24 -95.8(8) . . . . ?
P1 Ni1 C19 C24 95.6(3) . . . . ?
N2 Ni1 C19 C20 103.3(3) . . . . ?
N1 Ni1 C19 C20 72.6(8) . . . . ?
P1 Ni1 C19 C20 -96.0(3) . . . . ?
C24 C19 C20 C21 0.7(5) . . . . ?
Ni1 C19 C20 C21 -168.2(3) . . . . ?
C19 C20 C21 C22 -0.3(6) . . . . ?
C20 C21 C22 C23 -0.3(7) . . . . ?
C21 C22 C23 C24 0.6(6) . . . . ?
C22 C23 C24 C19 -0.2(6) . . . . ?
C20 C19 C24 C23 -0.4(5) . . . . ?
Ni1 C19 C24 C23 168.3(3) . . . . ?
C37 P1 C25 C30 -115.3(3) . . . . ?
C31 P1 C25 C30 140.0(3) . . . . ?
Ni1 P1 C25 C30 10.9(3) . . . . ?
C37 P1 C25 C26 67.6(3) . . . . ?
C31 P1 C25 C26 -37.0(3) . . . . ?
Ni1 P1 C25 C26 -166.1(2) . . . . ?
C30 C25 C26 C27 -0.5(5) . . . . ?
P1 C25 C26 C27 176.6(3) . . . . ?
C25 C26 C27 C28 0.8(5) . . . . ?
C26 C27 C28 C29 0.4(6) . . . . ?
C27 C28 C29 C30 -1.8(5) . . . . ?
C28 C29 C30 C25 2.2(5) . . . . ?
C26 C25 C30 C29 -1.0(5) . . . . ?
P1 C25 C30 C29 -178.1(3) . . . . ?
C25 P1 C31 C36 119.9(3) . . . . ?
C37 P1 C31 C36 9.6(3) . . . . ?
Ni1 P1 C31 C36 -112.3(3) . . . . ?
C25 P1 C31 C32 -56.9(3) . . . . ?
C37 P1 C31 C32 -167.2(3) . . . . ?
Ni1 P1 C31 C32 70.8(3) . . . . ?
C36 C31 C32 C33 1.2(5) . . . . ?
P1 C31 C32 C33 178.2(3) . . . . ?
C31 C32 C33 C34 -0.4(6) . . . . ?
C32 C33 C34 C35 -1.0(6) . . . . ?
C33 C34 C35 C36 1.4(6) . . . . ?
C32 C31 C36 C35 -0.8(5) . . . . ?
P1 C31 C36 C35 -177.6(3) . . . . ?
C34 C35 C36 C31 -0.5(6) . . . . ?
C25 P1 C37 C38 -15.9(3) . . . . ?
C31 P1 C37 C38 87.6(3) . . . . ?
Ni1 P1 C37 C38 -145.3(3) . . . . ?
C25 P1 C37 C42 167.9(2) . . . . ?
C31 P1 C37 C42 -88.6(3) . . . . ?
Ni1 P1 C37 C42 38.5(3) . . . . ?
C42 C37 C38 C39 0.7(5) . . . . ?
P1 C37 C38 C39 -175.4(3) . . . . ?
C37 C38 C39 C40 -0.1(5) . . . . ?
C38 C39 C40 C41 -0.8(6) . . . . ?
C39 C40 C41 C42 1.0(5) . . . . ?
C40 C41 C42 C37 -0.4(5) . . . . ?
C38 C37 C42 C41 -0.5(5) . . . . ?
P1 C37 C42 C41 175.9(3) . . . . ?

_refine_diff_density_max         0.443
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.075


####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1853548'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         '2(C43 H37 N2 Ni P), C6 H14'
_chemical_formula_sum            'C92 H88 N4 Ni2 P2'
_chemical_melting_point          ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         1429.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'
_chemical_absolute_configuration ?

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

_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.
;

_cell_length_a                   10.3715(15)
_cell_length_b                   33.585(5)
_cell_length_c                   10.5727(17)
_cell_angle_alpha                90
_cell_angle_beta                 94.5720(10)
_cell_angle_gamma                90
_cell_volume                     3671.0(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1298
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      25.77
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             1508
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.608
_shelx_estimated_absorpt_T_min   0.920
_shelx_estimated_absorpt_T_max   0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37217
_diffrn_reflns_av_unetI/netI     0.2571
_diffrn_reflns_av_R_equivalents  0.1798
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.648
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             13022
_reflns_number_gt                6110
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.964
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP and Mercury'
_computing_publication_material  enCIFer
_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)+(0.0864P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0056(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.59(4)
_refine_ls_number_reflns         13022
_refine_ls_number_parameters     909
_refine_ls_number_restraints     61
_refine_ls_R_factor_all          0.2049
_refine_ls_R_factor_gt           0.0861
_refine_ls_wR_factor_ref         0.2088
_refine_ls_wR_factor_gt          0.1720
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_restrained_S_all      0.910
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1A Ni 0.66235(17) 0.01872(6) 0.25418(17) 0.0217(5) Uani 1 1 d . . . . .
P1A P 0.8722(4) 0.01790(14) 0.2578(4) 0.0224(10) Uani 1 1 d . . . . .
N1A N 0.6227(11) 0.0433(4) 0.4110(11) 0.019(3) Uani 1 1 d . U . . .
N2A N 0.4918(13) 0.0398(4) 0.1931(13) 0.024(3) Uani 1 1 d . . . . .
C2A C 0.5181(15) 0.0690(5) 0.3937(15) 0.027(4) Uani 1 1 d . U . . .
C3A C 0.4906(19) 0.0901(6) 0.5022(18) 0.032(5) Uani 1 1 d . . . . .
H3A H 0.426289 0.109863 0.510813 0.038 Uiso 1 1 calc R U . . .
C4A C 0.5832(18) 0.0746(5) 0.5971(17) 0.036(5) Uani 1 1 d . . . . .
H4A H 0.592986 0.082180 0.683901 0.043 Uiso 1 1 calc R U . . .
C5A C 0.6551(16) 0.0467(5) 0.5389(18) 0.031(5) Uani 1 1 d . . . . .
C6A C 0.4488(15) 0.0652(5) 0.2724(16) 0.028(4) Uani 1 1 d . . . . .
H6A H 0.373646 0.080598 0.250340 0.033 Uiso 1 1 calc R U . . .
C7A C 0.7552(14) 0.0204(6) 0.6036(14) 0.028(4) Uani 1 1 d . . . . .
C8A C 0.8372(17) 0.0345(5) 0.7050(15) 0.033(5) Uani 1 1 d . . . . .
H8A H 0.829126 0.061395 0.731239 0.039 Uiso 1 1 calc R U . . .
C9A C 0.9295(16) 0.0107(6) 0.7684(16) 0.043(5) Uani 1 1 d . . . . .
H9A H 0.985011 0.021076 0.836267 0.051 Uiso 1 1 calc R U . . .
C10A C 0.9398(18) -0.0279(6) 0.7320(17) 0.034(5) Uani 1 1 d . . . . .
H10A H 1.002452 -0.044557 0.775811 0.041 Uiso 1 1 calc R U . . .
C11A C 0.8589(18) -0.0437(5) 0.6303(16) 0.037(5) Uani 1 1 d . . . . .
H11A H 0.866571 -0.070806 0.606335 0.044 Uiso 1 1 calc R U . . .
C12A C 0.7682(18) -0.0192(5) 0.5659(16) 0.034(5) Uani 1 1 d . . . . .
H12A H 0.714898 -0.029373 0.496076 0.041 Uiso 1 1 calc R U . . .
C13A C 0.4171(15) 0.0324(5) 0.0757(15) 0.022(4) Uani 1 1 d . . . . .
C14A C 0.4198(15) 0.0588(5) -0.0276(17) 0.031(4) Uani 1 1 d . . . . .
C15A C 0.353(2) 0.0484(7) -0.1423(18) 0.047(6) Uani 1 1 d . . . . .
H15A H 0.352465 0.066097 -0.212285 0.056 Uiso 1 1 calc R U . . .
C16A C 0.2863(17) 0.0130(6) -0.1565(16) 0.039(5) Uani 1 1 d . . . . .
H16A H 0.245249 0.005575 -0.236630 0.047 Uiso 1 1 calc R U . . .
C17A C 0.2802(16) -0.0120(6) -0.0512(17) 0.036(5) Uani 1 1 d . . . . .
H17A H 0.230879 -0.035814 -0.058814 0.043 Uiso 1 1 calc R U . . .
C18A C 0.3457(18) -0.0022(6) 0.0649(18) 0.034(5) Uani 1 1 d . . . . .
C19A C 0.4907(19) 0.0986(6) -0.018(2) 0.048(6) Uani 1 1 d . . . . .
H19A H 0.526699 0.104555 -0.098432 0.072 Uiso 1 1 calc R U . . .
H19B H 0.560870 0.097178 0.049999 0.072 Uiso 1 1 calc R U . . .
H19C H 0.430018 0.119688 0.002002 0.072 Uiso 1 1 calc R U . . .
C20A C 0.3381(17) -0.0284(5) 0.1804(17) 0.040(5) Uani 1 1 d . . . . .
H20A H 0.280550 -0.050932 0.158940 0.059 Uiso 1 1 calc R U . . .
H20B H 0.304113 -0.012872 0.248892 0.059 Uiso 1 1 calc R U . . .
H20C H 0.424641 -0.038250 0.208099 0.059 Uiso 1 1 calc R U . . .
C21A C 0.6704(13) -0.0160(4) 0.1114(14) 0.014(3) Uani 1 1 d . U . . .
C22A C 0.6632(15) -0.0071(5) -0.0132(16) 0.030(4) Uani 1 1 d . . . . .
H22A H 0.664171 0.020096 -0.038001 0.036 Uiso 1 1 calc R U . . .
C23A C 0.6545(15) -0.0363(6) -0.1065(16) 0.029(4) Uani 1 1 d . . . . .
H23A H 0.649056 -0.028850 -0.193507 0.035 Uiso 1 1 calc R U . . .
C24A C 0.6537(16) -0.0762(6) -0.0733(18) 0.038(5) Uani 1 1 d . . . . .
H24A H 0.651727 -0.096329 -0.136633 0.046 Uiso 1 1 calc R U . . .
C25A C 0.6558(16) -0.0864(5) 0.0562(18) 0.038(5) Uani 1 1 d . . . . .
H25A H 0.651249 -0.113420 0.081895 0.046 Uiso 1 1 calc R U . . .
C26A C 0.6646(14) -0.0564(5) 0.1436(18) 0.031(4) Uani 1 1 d . . . . .
H26A H 0.666884 -0.063336 0.230905 0.037 Uiso 1 1 calc R U . . .
C27A C 0.9474(15) -0.0295(5) 0.2274(15) 0.023(4) Uani 1 1 d . . . . .
C28A C 0.9735(14) -0.0419(5) 0.1080(16) 0.023(4) Uani 1 1 d . U . . .
H28A H 0.962362 -0.023763 0.039079 0.028 Uiso 1 1 calc R U . . .
C29A C 1.0153(15) -0.0801(5) 0.0858(17) 0.027(4) Uani 1 1 d . . . . .
H29A H 1.030570 -0.088140 0.002151 0.033 Uiso 1 1 calc R U . . .
C30A C 1.0347(17) -0.1065(5) 0.1838(18) 0.042(5) Uani 1 1 d . . . . .
H30A H 1.064947 -0.132681 0.169703 0.050 Uiso 1 1 calc R U . . .
C31A C 1.0094(17) -0.0941(5) 0.3041(17) 0.038(5) Uani 1 1 d . . . . .
H31A H 1.020375 -0.112393 0.372587 0.046 Uiso 1 1 calc R U . . .
C32A C 0.9695(15) -0.0566(5) 0.3272(15) 0.026(4) Uani 1 1 d . . . . .
H32A H 0.956435 -0.048743 0.411494 0.031 Uiso 1 1 calc R U . . .
C33A C 0.9188(14) 0.0511(5) 0.1333(14) 0.026(4) Uani 1 1 d . . . . .
C34A C 1.0461(17) 0.0563(5) 0.1079(15) 0.027(4) Uani 1 1 d . . . . .
H34A H 1.111028 0.040347 0.151335 0.033 Uiso 1 1 calc R U . . .
C35A C 1.0821(19) 0.0844(7) 0.0202(19) 0.044(6) Uani 1 1 d . . . . .
H35A H 1.170267 0.087103 0.003083 0.052 Uiso 1 1 calc R U . . .
C36A C 0.9894(17) 0.1081(5) -0.0413(16) 0.032(4) Uani 1 1 d . . . . .
H36A H 1.012617 0.127005 -0.102460 0.039 Uiso 1 1 calc R U . . .
C37A C 0.8619(15) 0.1044(5) -0.0138(16) 0.028(4) Uani 1 1 d . . . . .
H37A H 0.798235 0.121376 -0.054440 0.034 Uiso 1 1 calc R U . . .
C38A C 0.8249(16) 0.0756(5) 0.0740(15) 0.027(4) Uani 1 1 d . . . . .
H38A H 0.736947 0.073158 0.092037 0.032 Uiso 1 1 calc R U . . .
C39A C 0.9701(17) 0.0420(5) 0.3924(16) 0.025(5) Uani 1 1 d . . . . .
C40A C 0.9279(16) 0.0759(5) 0.4356(15) 0.022(4) Uani 1 1 d . . . . .
H40A H 0.844890 0.085543 0.405539 0.026 Uiso 1 1 calc R U . . .
C41A C 1.0047(18) 0.0980(5) 0.5259(15) 0.033(5) Uani 1 1 d . . . . .
H41A H 0.973182 0.122326 0.557115 0.039 Uiso 1 1 calc R U . . .
C42A C 1.1261(17) 0.0844(5) 0.5694(15) 0.030(4) Uani 1 1 d . U . . .
H42A H 1.178219 0.098976 0.631196 0.036 Uiso 1 1 calc R U . . .
C43A C 1.1690(17) 0.0497(6) 0.5216(19) 0.047(6) Uani 1 1 d . . . . .
H43A H 1.252316 0.040299 0.551234 0.057 Uiso 1 1 calc R U . . .
C44A C 1.0961(15) 0.0276(5) 0.4314(15) 0.031(5) Uani 1 1 d . . . . .
H44A H 1.128769 0.003857 0.397058 0.037 Uiso 1 1 calc R U . . .
Ni1B Ni 0.04067(17) 0.24996(6) 0.99334(18) 0.0209(5) Uani 1 1 d . . . . .
P1B P -0.1686(4) 0.25094(14) 0.9927(4) 0.0193(9) Uani 1 1 d . . . . .
N1B N 0.0799(11) 0.2258(4) 0.8311(11) 0.020(3) Uani 1 1 d . U . . .
N2B N 0.2146(12) 0.2297(4) 1.0540(13) 0.028(4) Uani 1 1 d . . . . .
C2B C 0.1889(16) 0.2009(5) 0.8536(18) 0.028(4) Uani 1 1 d . . . . .
C3B C 0.2118(19) 0.1820(6) 0.7405(18) 0.030(5) Uani 1 1 d . U . . .
H3B H 0.278910 0.163490 0.727775 0.036 Uiso 1 1 calc R U . . .
C4B C 0.1190(15) 0.1952(5) 0.6512(16) 0.030(4) Uani 1 1 d . U . . .
H4B H 0.109763 0.186989 0.564971 0.036 Uiso 1 1 calc R U . . .
C5B C 0.0394(15) 0.2227(5) 0.7077(16) 0.026(4) Uani 1 1 d . U . . .
C6B C 0.2569(17) 0.2050(5) 0.9710(17) 0.031(4) Uani 1 1 d . . . . .
H6B H 0.333682 0.190133 0.991011 0.037 Uiso 1 1 calc R U . . .
C7B C -0.0601(14) 0.2471(6) 0.6445(14) 0.022(4) Uani 1 1 d . . . . .
C8B C -0.1372(18) 0.2322(6) 0.5378(17) 0.036(5) Uani 1 1 d . . . . .
H8B H -0.123387 0.205908 0.508471 0.043 Uiso 1 1 calc R U . . .
C9B C -0.2307(17) 0.2553(6) 0.4774(15) 0.037(5) Uani 1 1 d . . . . .
H9B H -0.282766 0.244579 0.407526 0.045 Uiso 1 1 calc R U . . .
C10B C -0.2515(18) 0.2936(6) 0.5150(16) 0.041(5) Uani 1 1 d . . . . .
H10B H -0.316709 0.309399 0.471362 0.049 Uiso 1 1 calc R U . . .
C11B C -0.1771(15) 0.3087(5) 0.6161(15) 0.029(4) Uani 1 1 d . . . . .
H11B H -0.192465 0.335194 0.642532 0.034 Uiso 1 1 calc R U . . .
C12B C -0.0799(15) 0.2868(5) 0.6817(14) 0.020(4) Uani 1 1 d . . . . .
H12B H -0.027929 0.298311 0.750238 0.024 Uiso 1 1 calc R U . . .
C13B C 0.2917(16) 0.2376(5) 1.1707(16) 0.026(4) Uani 1 1 d . . . . .
C14B C 0.2860(16) 0.2099(6) 1.2728(17) 0.034(5) Uani 1 1 d . . . . .
C15B C 0.3497(17) 0.2214(7) 1.3896(17) 0.035(5) Uani 1 1 d . . . . .
H15B H 0.347469 0.204392 1.461121 0.042 Uiso 1 1 calc R U . . .
C16B C 0.4151(16) 0.2569(6) 1.4014(16) 0.037(5) Uani 1 1 d . . . . .
H16B H 0.455099 0.264519 1.481787 0.044 Uiso 1 1 calc R U . . .
C17B C 0.4235(17) 0.2813(6) 1.3005(19) 0.042(5) Uani 1 1 d . . . . .
H17B H 0.474946 0.304713 1.309178 0.051 Uiso 1 1 calc R U . . .
C18B C 0.3588(14) 0.2726(5) 1.1862(16) 0.025(4) Uani 1 1 d . . . . .
C19B C 0.2157(19) 0.1708(6) 1.2620(18) 0.046(6) Uani 1 1 d . . . . .
H19D H 0.133450 0.173089 1.301165 0.068 Uiso 1 1 calc R U . . .
H19E H 0.268858 0.150082 1.305578 0.068 Uiso 1 1 calc R U . . .
H19F H 0.198790 0.163749 1.172302 0.068 Uiso 1 1 calc R U . . .
C20B C 0.3711(17) 0.2998(5) 1.0730(16) 0.032(5) Uani 1 1 d . . . . .
H20D H 0.460902 0.299712 1.050218 0.048 Uiso 1 1 calc R U . . .
H20E H 0.346228 0.326923 1.094781 0.048 Uiso 1 1 calc R U . . .
H20F H 0.314226 0.290247 1.000856 0.048 Uiso 1 1 calc R U . . .
C21B C 0.0373(13) 0.2831(5) 1.1386(14) 0.018(4) Uani 1 1 d . U . . .
C22B C 0.0531(14) 0.3226(5) 1.1136(15) 0.021(4) Uani 1 1 d . . . . .
H22B H 0.050139 0.330494 1.027180 0.025 Uiso 1 1 calc R U . . .
C23B C 0.0732(16) 0.3519(5) 1.2047(17) 0.034(5) Uani 1 1 d . . . . .
H23B H 0.086251 0.378887 1.181634 0.041 Uiso 1 1 calc R U . . .
C24B C 0.0735(15) 0.3405(6) 1.3330(16) 0.032(4) Uani 1 1 d . . . . .
H24B H 0.085545 0.359693 1.398884 0.039 Uiso 1 1 calc R U . . .
C25B C 0.0566(15) 0.3022(5) 1.3598(16) 0.029(4) Uani 1 1 d . . . . .
H25B H 0.057460 0.294524 1.446403 0.034 Uiso 1 1 calc R U . . .
C26B C 0.0375(13) 0.2725(5) 1.2666(14) 0.020(4) Uani 1 1 d . . . . .
H26B H 0.024829 0.245592 1.290169 0.024 Uiso 1 1 calc R U . . .
C27B C -0.2495(14) 0.2977(5) 1.0255(16) 0.024(4) Uani 1 1 d . . . . .
C28B C -0.2828(16) 0.3247(5) 0.9306(18) 0.037(5) Uani 1 1 d . . . . .
H28B H -0.274090 0.317454 0.844808 0.044 Uiso 1 1 calc R U . . .
C29B C -0.3290(15) 0.3622(5) 0.9577(18) 0.034(5) Uani 1 1 d . . . . .
H29B H -0.354128 0.380089 0.890574 0.041 Uiso 1 1 calc R U . . .
C30B C -0.3384(13) 0.3736(5) 1.0824(17) 0.031(4) Uani 1 1 d . . . . .
H30B H -0.371437 0.399178 1.101069 0.038 Uiso 1 1 calc R U . . .
C31B C -0.2995(16) 0.3477(5) 1.1800(16) 0.029(4) Uani 1 1 d . . . . .
H31B H -0.302484 0.355984 1.265608 0.035 Uiso 1 1 calc R U . . .
C32B C -0.2567(14) 0.3101(5) 1.1545(17) 0.030(4) Uani 1 1 d . . . . .
H32B H -0.231922 0.292347 1.222003 0.036 Uiso 1 1 calc R U . . .
C33B C -0.2173(15) 0.2160(4) 1.1169(15) 0.020(4) Uani 1 1 d . . . . .
C34B C -0.1270(16) 0.1901(5) 1.1717(16) 0.030(4) Uani 1 1 d . . . . .
H34B H -0.039284 0.192498 1.152991 0.036 Uiso 1 1 calc R U . . .
C35B C -0.1608(18) 0.1613(5) 1.2519(18) 0.035(5) Uani 1 1 d . . . . .
H35B H -0.097943 0.142828 1.285944 0.042 Uiso 1 1 calc R U . . .
C36B C -0.2831(16) 0.1588(5) 1.2832(15) 0.029(4) Uani 1 1 d . . . . .
H36B H -0.305881 0.139097 1.341959 0.034 Uiso 1 1 calc R U . . .
C37B C -0.3794(17) 0.1854(5) 1.2294(15) 0.026(4) Uani 1 1 d . . . . .
H37B H -0.466613 0.183026 1.249686 0.032 Uiso 1 1 calc R U . . .
C38B C -0.3453(15) 0.2139(5) 1.1495(17) 0.028(5) Uani 1 1 d . . . . .
H38B H -0.407622 0.232536 1.115376 0.033 Uiso 1 1 calc R U . . .
C39B C -0.2714(15) 0.2290(5) 0.8629(15) 0.021(4) Uani 1 1 d . . . . .
C40B C -0.2254(17) 0.1929(5) 0.8107(16) 0.029(4) Uani 1 1 d . . . . .
H40B H -0.140609 0.183843 0.836619 0.034 Uiso 1 1 calc R U . . .
C41B C -0.3004(18) 0.1714(5) 0.7246(16) 0.033(5) Uani 1 1 d . . . . .
H41B H -0.268201 0.147551 0.690449 0.040 Uiso 1 1 calc R U . . .
C42B C -0.4220(18) 0.1842(5) 0.6878(18) 0.041(5) Uani 1 1 d . . . . .
H42B H -0.475598 0.168579 0.630054 0.049 Uiso 1 1 calc R U . . .
C43B C -0.4686(16) 0.2194(5) 0.7327(14) 0.028(4) Uani 1 1 d . . . . .
H43B H -0.552580 0.228468 0.703884 0.034 Uiso 1 1 calc R U . . .
C44B C -0.3924(15) 0.2413(5) 0.8200(16) 0.031(5) Uani 1 1 d . . . . .
H44B H -0.425005 0.265553 0.850984 0.037 Uiso 1 1 calc R U . . .
C1 C -0.721(3) 0.3132(10) 1.693(2) 0.109(12) Uani 1 1 d . . . . .
H1A H -0.794095 0.331871 1.688122 0.164 Uiso 1 1 calc R U . . .
H1B H -0.714437 0.300215 1.776402 0.164 Uiso 1 1 calc R U . . .
H1C H -0.735319 0.293023 1.626539 0.164 Uiso 1 1 calc R U . . .
C2 C -0.594(3) 0.3363(11) 1.675(3) 0.121(13) Uani 1 1 d . . . . .
H2A H -0.567222 0.351072 1.753466 0.145 Uiso 1 1 calc R U . . .
H2B H -0.524567 0.316914 1.659973 0.145 Uiso 1 1 calc R U . . .
C3 C -0.606(4) 0.3629(9) 1.574(3) 0.138(16) Uani 1 1 d . . . . .
H3C H -0.680817 0.380299 1.586221 0.165 Uiso 1 1 calc R U . . .
H3D H -0.627402 0.347341 1.495551 0.165 Uiso 1 1 calc R U . . .
C4 C -0.489(3) 0.3901(9) 1.550(3) 0.098(9) Uani 1 1 d . . . . .
H4C H -0.483277 0.408403 1.624034 0.117 Uiso 1 1 calc R U . . .
H4D H -0.413459 0.372232 1.563623 0.117 Uiso 1 1 calc R U . . .
C5 C -0.461(5) 0.4134(12) 1.452(4) 0.25(3) Uani 1 1 d . . . . .
H5A H -0.541875 0.428558 1.431888 0.298 Uiso 1 1 calc R U . . .
H5B H -0.456138 0.394279 1.381428 0.298 Uiso 1 1 calc R U . . .
C6 C -0.363(3) 0.4412(10) 1.432(4) 0.156(17) Uani 1 1 d . . . . .
H6C H -0.369571 0.463786 1.489689 0.234 Uiso 1 1 calc R U . . .
H6D H -0.373624 0.450633 1.343942 0.234 Uiso 1 1 calc R U . . .
H6E H -0.278388 0.428505 1.447816 0.234 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
Ni1A C21A 1.915(15) . ?
Ni1A N1A 1.925(12) . ?
Ni1A N2A 1.966(14) . ?
Ni1A P1A 2.174(4) . ?
P1A C27A 1.812(17) . ?
P1A C33A 1.819(17) . ?
P1A C39A 1.866(17) . ?
N1A C5A 1.37(2) . ?
N1A C2A 1.39(2) . ?
N2A C6A 1.298(19) . ?
N2A C13A 1.432(19) . ?
C2A C3A 1.40(2) . ?
C2A C6A 1.43(2) . ?
C3A C4A 1.43(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.37(2) . ?
C4A H4A 0.9500 . ?
C5A C7A 1.49(2) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.40(2) . ?
C7A C12A 1.40(2) . ?
C8A C9A 1.38(2) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.36(3) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.41(2) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.39(2) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
C13A C18A 1.38(2) . ?
C13A C14A 1.41(2) . ?
C14A C15A 1.40(2) . ?
C14A C19A 1.52(2) . ?
C15A C16A 1.37(3) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.40(2) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.39(2) . ?
C17A H17A 0.9500 . ?
C18A C20A 1.51(3) . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
C21A C22A 1.35(2) . ?
C21A C26A 1.40(2) . ?
C22A C23A 1.39(2) . ?
C22A H22A 0.9500 . ?
C23A C24A 1.39(2) . ?
C23A H23A 0.9500 . ?
C24A C25A 1.41(2) . ?
C24A H24A 0.9500 . ?
C25A C26A 1.36(2) . ?
C25A H25A 0.9500 . ?
C26A H26A 0.9500 . ?
C27A C28A 1.38(2) . ?
C27A C32A 1.40(2) . ?
C28A C29A 1.38(2) . ?
C28A H28A 0.9500 . ?
C29A C30A 1.36(2) . ?
C29A H29A 0.9500 . ?
C30A C31A 1.38(2) . ?
C30A H30A 0.9500 . ?
C31A C32A 1.35(2) . ?
C31A H31A 0.9500 . ?
C32A H32A 0.9500 . ?
C33A C38A 1.39(2) . ?
C33A C34A 1.38(2) . ?
C34A C35A 1.39(3) . ?
C34A H34A 0.9500 . ?
C35A C36A 1.37(3) . ?
C35A H35A 0.9500 . ?
C36A C37A 1.38(2) . ?
C36A H36A 0.9500 . ?
C37A C38A 1.41(2) . ?
C37A H37A 0.9500 . ?
C38A H38A 0.9500 . ?
C39A C40A 1.32(2) . ?
C39A C44A 1.42(2) . ?
C40A C41A 1.41(2) . ?
C40A H40A 0.9500 . ?
C41A C42A 1.38(2) . ?
C41A H41A 0.9500 . ?
C42A C43A 1.36(2) . ?
C42A H42A 0.9500 . ?
C43A C44A 1.39(2) . ?
C43A H43A 0.9500 . ?
C44A H44A 0.9500 . ?
Ni1B C21B 1.899(15) . ?
Ni1B N1B 1.969(12) . ?
Ni1B N2B 1.986(13) . ?
Ni1B P1B 2.171(4) . ?
P1B C39B 1.823(16) . ?
P1B C27B 1.828(16) . ?
P1B C33B 1.860(16) . ?
N1B C5B 1.342(19) . ?
N1B C2B 1.41(2) . ?
N2B C6B 1.31(2) . ?
N2B C13B 1.44(2) . ?
C2B C6B 1.38(2) . ?
C2B C3B 1.39(2) . ?
C3B C4B 1.37(2) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.40(2) . ?
C4B H4B 0.9500 . ?
C5B C7B 1.44(2) . ?
C6B H6B 0.9500 . ?
C7B C12B 1.41(2) . ?
C7B C8B 1.42(2) . ?
C8B C9B 1.36(2) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.37(3) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.37(2) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.39(2) . ?
C11B H11B 0.9500 . ?
C12B H12B 0.9500 . ?
C13B C18B 1.37(2) . ?
C13B C14B 1.43(2) . ?
C14B C15B 1.41(2) . ?
C14B C19B 1.50(3) . ?
C15B C16B 1.37(3) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.35(3) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.37(2) . ?
C17B H17B 0.9500 . ?
C18B C20B 1.52(2) . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?
C20B H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 0.9800 . ?
C21B C22B 1.36(2) . ?
C21B C26B 1.40(2) . ?
C22B C23B 1.38(2) . ?
C22B H22B 0.9500 . ?
C23B C24B 1.41(2) . ?
C23B H23B 0.9500 . ?
C24B C25B 1.33(2) . ?
C24B H24B 0.9500 . ?
C25B C26B 1.40(2) . ?
C25B H25B 0.9500 . ?
C26B H26B 0.9500 . ?
C27B C28B 1.38(2) . ?
C27B C32B 1.43(2) . ?
C28B C29B 1.39(2) . ?
C28B H28B 0.9500 . ?
C29B C30B 1.38(2) . ?
C29B H29B 0.9500 . ?
C30B C31B 1.39(2) . ?
C30B H30B 0.9500 . ?
C31B C32B 1.37(2) . ?
C31B H31B 0.9500 . ?
C32B H32B 0.9500 . ?
C33B C34B 1.37(2) . ?
C33B C38B 1.40(2) . ?
C34B C35B 1.35(2) . ?
C34B H34B 0.9500 . ?
C35B C36B 1.34(2) . ?
C35B H35B 0.9500 . ?
C36B C37B 1.42(2) . ?
C36B H36B 0.9500 . ?
C37B C38B 1.34(2) . ?
C37B H37B 0.9500 . ?
C38B H38B 0.9500 . ?
C39B C44B 1.36(2) . ?
C39B C40B 1.43(2) . ?
C40B C41B 1.36(2) . ?
C40B H40B 0.9500 . ?
C41B C42B 1.36(2) . ?
C41B H41B 0.9500 . ?
C42B C43B 1.38(2) . ?
C42B H42B 0.9500 . ?
C43B C44B 1.38(2) . ?
C43B H43B 0.9500 . ?
C44B H44B 0.9500 . ?
C1 C2 1.56(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.39(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.55(4) . ?
C3 H3C 0.9900 . ?
C3 H3D 0.9900 . ?
C4 C5 1.35(4) . ?
C4 H4C 0.9900 . ?
C4 H4D 0.9900 . ?
C5 C6 1.41(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6C 0.9800 . ?
C6 H6D 0.9800 . ?
C6 H6E 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
C21A Ni1A N1A 164.9(6) . . ?
C21A Ni1A N2A 93.2(6) . . ?
N1A Ni1A N2A 83.1(5) . . ?
C21A Ni1A P1A 84.2(4) . . ?
N1A Ni1A P1A 105.8(4) . . ?
N2A Ni1A P1A 152.0(4) . . ?
C27A P1A C33A 105.5(8) . . ?
C27A P1A C39A 107.4(8) . . ?
C33A P1A C39A 97.3(7) . . ?
C27A P1A Ni1A 116.9(5) . . ?
C33A P1A Ni1A 107.6(5) . . ?
C39A P1A Ni1A 119.4(6) . . ?
C5A N1A C2A 101.8(13) . . ?
C5A N1A Ni1A 146.4(12) . . ?
C2A N1A Ni1A 111.9(10) . . ?
C6A N2A C13A 119.0(14) . . ?
C6A N2A Ni1A 111.7(11) . . ?
C13A N2A Ni1A 129.2(11) . . ?
N1A C2A C3A 114.6(15) . . ?
N1A C2A C6A 113.2(15) . . ?
C3A C2A C6A 131.6(16) . . ?
C2A C3A C4A 102.8(16) . . ?
C2A C3A H3A 128.6 . . ?
C4A C3A H3A 128.6 . . ?
C5A C4A C3A 107.0(16) . . ?
C5A C4A H4A 126.5 . . ?
C3A C4A H4A 126.5 . . ?
C4A C5A N1A 113.6(16) . . ?
C4A C5A C7A 125.7(17) . . ?
N1A C5A C7A 120.7(16) . . ?
N2A C6A C2A 117.8(15) . . ?
N2A C6A H6A 121.1 . . ?
C2A C6A H6A 121.1 . . ?
C8A C7A C12A 118.3(16) . . ?
C8A C7A C5A 120.7(17) . . ?
C12A C7A C5A 121.0(15) . . ?
C9A C8A C7A 122.1(18) . . ?
C9A C8A H8A 118.9 . . ?
C7A C8A H8A 118.9 . . ?
C10A C9A C8A 118.9(16) . . ?
C10A C9A H9A 120.6 . . ?
C8A C9A H9A 120.6 . . ?
C9A C10A C11A 121.2(18) . . ?
C9A C10A H10A 119.4 . . ?
C11A C10A H10A 119.4 . . ?
C12A C11A C10A 119.3(17) . . ?
C12A C11A H11A 120.4 . . ?
C10A C11A H11A 120.4 . . ?
C11A C12A C7A 120.1(16) . . ?
C11A C12A H12A 119.9 . . ?
C7A C12A H12A 119.9 . . ?
C18A C13A C14A 120.7(16) . . ?
C18A C13A N2A 118.0(15) . . ?
C14A C13A N2A 121.3(15) . . ?
C15A C14A C13A 118.4(17) . . ?
C15A C14A C19A 119.1(17) . . ?
C13A C14A C19A 122.5(16) . . ?
C16A C15A C14A 121.6(19) . . ?
C16A C15A H15A 119.2 . . ?
C14A C15A H15A 119.2 . . ?
C15A C16A C17A 119.0(17) . . ?
C15A C16A H16A 120.5 . . ?
C17A C16A H16A 120.5 . . ?
C18A C17A C16A 120.6(18) . . ?
C18A C17A H17A 119.7 . . ?
C16A C17A H17A 119.7 . . ?
C13A C18A C17A 119.6(18) . . ?
C13A C18A C20A 119.1(16) . . ?
C17A C18A C20A 121.4(18) . . ?
C14A C19A H19A 109.5 . . ?
C14A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C14A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C18A C20A H20A 109.5 . . ?
C18A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C18A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C22A C21A C26A 117.0(15) . . ?
C22A C21A Ni1A 129.2(12) . . ?
C26A C21A Ni1A 113.2(12) . . ?
C21A C22A C23A 122.2(17) . . ?
C21A C22A H22A 118.9 . . ?
C23A C22A H22A 118.9 . . ?
C24A C23A C22A 120.3(17) . . ?
C24A C23A H23A 119.9 . . ?
C22A C23A H23A 119.9 . . ?
C23A C24A C25A 118.7(17) . . ?
C23A C24A H24A 120.6 . . ?
C25A C24A H24A 120.6 . . ?
C26A C25A C24A 118.3(17) . . ?
C26A C25A H25A 120.8 . . ?
C24A C25A H25A 120.8 . . ?
C25A C26A C21A 123.4(18) . . ?
C25A C26A H26A 118.3 . . ?
C21A C26A H26A 118.3 . . ?
C28A C27A C32A 117.4(15) . . ?
C28A C27A P1A 123.2(12) . . ?
C32A C27A P1A 119.1(13) . . ?
C29A C28A C27A 121.7(16) . . ?
C29A C28A H28A 119.2 . . ?
C27A C28A H28A 119.2 . . ?
C30A C29A C28A 120.2(17) . . ?
C30A C29A H29A 119.9 . . ?
C28A C29A H29A 119.9 . . ?
C29A C30A C31A 118.4(16) . . ?
C29A C30A H30A 120.8 . . ?
C31A C30A H30A 120.8 . . ?
C32A C31A C30A 122.0(16) . . ?
C32A C31A H31A 119.0 . . ?
C30A C31A H31A 119.0 . . ?
C31A C32A C27A 120.3(15) . . ?
C31A C32A H32A 119.8 . . ?
C27A C32A H32A 119.8 . . ?
C38A C33A C34A 119.0(16) . . ?
C38A C33A P1A 118.3(12) . . ?
C34A C33A P1A 122.2(13) . . ?
C33A C34A C35A 121.8(17) . . ?
C33A C34A H34A 119.1 . . ?
C35A C34A H34A 119.1 . . ?
C36A C35A C34A 119.5(18) . . ?
C36A C35A H35A 120.2 . . ?
C34A C35A H35A 120.2 . . ?
C35A C36A C37A 119.6(18) . . ?
C35A C36A H36A 120.2 . . ?
C37A C36A H36A 120.2 . . ?
C36A C37A C38A 121.1(16) . . ?
C36A C37A H37A 119.5 . . ?
C38A C37A H37A 119.5 . . ?
C33A C38A C37A 119.0(15) . . ?
C33A C38A H38A 120.5 . . ?
C37A C38A H38A 120.5 . . ?
C40A C39A C44A 121.1(16) . . ?
C40A C39A P1A 117.6(13) . . ?
C44A C39A P1A 120.4(14) . . ?
C39A C40A C41A 120.4(17) . . ?
C39A C40A H40A 119.8 . . ?
C41A C40A H40A 119.8 . . ?
C42A C41A C40A 120.3(17) . . ?
C42A C41A H41A 119.9 . . ?
C40A C41A H41A 119.9 . . ?
C43A C42A C41A 118.4(16) . . ?
C43A C42A H42A 120.8 . . ?
C41A C42A H42A 120.8 . . ?
C42A C43A C44A 122.6(16) . . ?
C42A C43A H43A 118.7 . . ?
C44A C43A H43A 118.7 . . ?
C43A C44A C39A 117.1(16) . . ?
C43A C44A H44A 121.4 . . ?
C39A C44A H44A 121.4 . . ?
C21B Ni1B N1B 164.6(6) . . ?
C21B Ni1B N2B 90.8(6) . . ?
N1B Ni1B N2B 84.0(5) . . ?
C21B Ni1B P1B 84.9(4) . . ?
N1B Ni1B P1B 106.2(4) . . ?
N2B Ni1B P1B 152.7(4) . . ?
C39B P1B C27B 103.9(7) . . ?
C39B P1B C33B 95.8(7) . . ?
C27B P1B C33B 104.7(7) . . ?
C39B P1B Ni1B 121.4(5) . . ?
C27B P1B Ni1B 119.1(5) . . ?
C33B P1B Ni1B 108.4(5) . . ?
C5B N1B C2B 107.6(14) . . ?
C5B N1B Ni1B 143.9(11) . . ?
C2B N1B Ni1B 108.4(10) . . ?
C6B N2B C13B 119.9(14) . . ?
C6B N2B Ni1B 110.2(11) . . ?
C13B N2B Ni1B 129.9(11) . . ?
C6B C2B C3B 135.0(17) . . ?
C6B C2B N1B 115.8(15) . . ?
C3B C2B N1B 108.4(15) . . ?
C4B C3B C2B 106.6(17) . . ?
C4B C3B H3B 126.7 . . ?
C2B C3B H3B 126.7 . . ?
C3B C4B C5B 109.0(15) . . ?
C3B C4B H4B 125.5 . . ?
C5B C4B H4B 125.5 . . ?
N1B C5B C4B 108.3(15) . . ?
N1B C5B C7B 124.4(15) . . ?
C4B C5B C7B 127.0(15) . . ?
N2B C6B C2B 119.4(16) . . ?
N2B C6B H6B 120.3 . . ?
C2B C6B H6B 120.3 . . ?
C12B C7B C8B 118.1(15) . . ?
C12B C7B C5B 121.6(14) . . ?
C8B C7B C5B 120.3(17) . . ?
C9B C8B C7B 120.4(18) . . ?
C9B C8B H8B 119.8 . . ?
C7B C8B H8B 119.8 . . ?
C8B C9B C10B 121.5(17) . . ?
C8B C9B H9B 119.2 . . ?
C10B C9B H9B 119.2 . . ?
C9B C10B C11B 119.0(18) . . ?
C9B C10B H10B 120.5 . . ?
C11B C10B H10B 120.5 . . ?
C10B C11B C12B 122.5(18) . . ?
C10B C11B H11B 118.8 . . ?
C12B C11B H11B 118.8 . . ?
C11B C12B C7B 118.5(15) . . ?
C11B C12B H12B 120.7 . . ?
C7B C12B H12B 120.7 . . ?
C18B C13B C14B 121.3(16) . . ?
C18B C13B N2B 120.2(15) . . ?
C14B C13B N2B 118.3(15) . . ?
C15B C14B C13B 116.0(18) . . ?
C15B C14B C19B 119.9(17) . . ?
C13B C14B C19B 124.1(15) . . ?
C16B C15B C14B 120.9(19) . . ?
C16B C15B H15B 119.6 . . ?
C14B C15B H15B 119.6 . . ?
C17B C16B C15B 121.1(17) . . ?
C17B C16B H16B 119.5 . . ?
C15B C16B H16B 119.5 . . ?
C16B C17B C18B 120.6(18) . . ?
C16B C17B H17B 119.7 . . ?
C18B C17B H17B 119.7 . . ?
C13B C18B C17B 120.0(17) . . ?
C13B C18B C20B 119.7(15) . . ?
C17B C18B C20B 120.1(16) . . ?
C14B C19B H19D 109.5 . . ?
C14B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C14B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C18B C20B H20D 109.5 . . ?
C18B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C18B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C22B C21B C26B 116.3(14) . . ?
C22B C21B Ni1B 113.8(12) . . ?
C26B C21B Ni1B 129.4(12) . . ?
C21B C22B C23B 124.9(16) . . ?
C21B C22B H22B 117.5 . . ?
C23B C22B H22B 117.5 . . ?
C22B C23B C24B 117.7(16) . . ?
C22B C23B H23B 121.2 . . ?
C24B C23B H23B 121.1 . . ?
C25B C24B C23B 118.5(17) . . ?
C25B C24B H24B 120.7 . . ?
C23B C24B H24B 120.7 . . ?
C24B C25B C26B 123.3(17) . . ?
C24B C25B H25B 118.3 . . ?
C26B C25B H25B 118.3 . . ?
C25B C26B C21B 119.2(15) . . ?
C25B C26B H26B 120.4 . . ?
C21B C26B H26B 120.4 . . ?
C28B C27B C32B 118.3(16) . . ?
C28B C27B P1B 121.3(14) . . ?
C32B C27B P1B 119.3(12) . . ?
C29B C28B C27B 121.2(18) . . ?
C29B C28B H28B 119.4 . . ?
C27B C28B H28B 119.4 . . ?
C28B C29B C30B 120.1(17) . . ?
C28B C29B H29B 120.0 . . ?
C30B C29B H29B 120.0 . . ?
C31B C30B C29B 119.7(16) . . ?
C31B C30B H30B 120.1 . . ?
C29B C30B H30B 120.1 . . ?
C32B C31B C30B 120.8(17) . . ?
C32B C31B H31B 119.6 . . ?
C30B C31B H31B 119.6 . . ?
C31B C32B C27B 119.8(16) . . ?
C31B C32B H32B 120.1 . . ?
C27B C32B H32B 120.1 . . ?
C34B C33B C38B 119.5(15) . . ?
C34B C33B P1B 118.9(13) . . ?
C38B C33B P1B 121.4(12) . . ?
C35B C34B C33B 121.1(17) . . ?
C35B C34B H34B 119.4 . . ?
C33B C34B H34B 119.4 . . ?
C36B C35B C34B 119.9(17) . . ?
C36B C35B H35B 120.0 . . ?
C34B C35B H35B 120.0 . . ?
C35B C36B C37B 120.6(16) . . ?
C35B C36B H36B 119.7 . . ?
C37B C36B H36B 119.7 . . ?
C38B C37B C36B 119.2(16) . . ?
C38B C37B H37B 120.4 . . ?
C36B C37B H37B 120.4 . . ?
C37B C38B C33B 119.6(16) . . ?
C37B C38B H38B 120.2 . . ?
C33B C38B H38B 120.2 . . ?
C44B C39B C40B 117.0(15) . . ?
C44B C39B P1B 126.6(13) . . ?
C40B C39B P1B 116.1(12) . . ?
C41B C40B C39B 121.3(16) . . ?
C41B C40B H40B 119.4 . . ?
C39B C40B H40B 119.4 . . ?
C40B C41B C42B 119.5(17) . . ?
C40B C41B H41B 120.2 . . ?
C42B C41B H41B 120.2 . . ?
C41B C42B C43B 121.1(16) . . ?
C41B C42B H42B 119.5 . . ?
C43B C42B H42B 119.5 . . ?
C42B C43B C44B 119.4(16) . . ?
C42B C43B H43B 120.3 . . ?
C44B C43B H43B 120.3 . . ?
C39B C44B C43B 121.6(17) . . ?
C39B C44B H44B 119.2 . . ?
C43B C44B H44B 119.2 . . ?
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 . . ?
C3 C2 C1 113(3) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 119(3) . . ?
C2 C3 H3C 107.7 . . ?
C4 C3 H3C 107.7 . . ?
C2 C3 H3D 107.7 . . ?
C4 C3 H3D 107.7 . . ?
H3C C3 H3D 107.1 . . ?
C5 C4 C3 133(4) . . ?
C5 C4 H4C 103.9 . . ?
C3 C4 H4C 103.9 . . ?
C5 C4 H4D 103.9 . . ?
C3 C4 H4D 103.9 . . ?
H4C C4 H4D 105.4 . . ?
C4 C5 C6 135(5) . . ?
C4 C5 H5A 103.5 . . ?
C6 C5 H5A 103.5 . . ?
C4 C5 H5B 103.5 . . ?
C6 C5 H5B 103.5 . . ?
H5A C5 H5B 105.3 . . ?
C5 C6 H6C 109.5 . . ?
C5 C6 H6D 109.5 . . ?
H6C C6 H6D 109.5 . . ?
C5 C6 H6E 109.5 . . ?
H6C C6 H6E 109.5 . . ?
H6D C6 H6E 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
C5A N1A C2A C3A 4.2(19) . . . . ?
Ni1A N1A C2A C3A -175.3(12) . . . . ?
C5A N1A C2A C6A -168.1(14) . . . . ?
Ni1A N1A C2A C6A 12.3(17) . . . . ?
N1A C2A C3A C4A -3(2) . . . . ?
C6A C2A C3A C4A 167.8(18) . . . . ?
C2A C3A C4A C5A 0(2) . . . . ?
C3A C4A C5A N1A 3(2) . . . . ?
C3A C4A C5A C7A -174.3(16) . . . . ?
C2A N1A C5A C4A -4.1(19) . . . . ?
Ni1A N1A C5A C4A 175.2(15) . . . . ?
C2A N1A C5A C7A 173.0(15) . . . . ?
Ni1A N1A C5A C7A -8(3) . . . . ?
C13A N2A C6A C2A 173.8(14) . . . . ?
Ni1A N2A C6A C2A -9.0(19) . . . . ?
N1A C2A C6A N2A -2(2) . . . . ?
C3A C2A C6A N2A -172.8(18) . . . . ?
C4A C5A C7A C8A -38(3) . . . . ?
N1A C5A C7A C8A 145.7(15) . . . . ?
C4A C5A C7A C12A 141.4(19) . . . . ?
N1A C5A C7A C12A -35(2) . . . . ?
C12A C7A C8A C9A 0(2) . . . . ?
C5A C7A C8A C9A 178.9(16) . . . . ?
C7A C8A C9A C10A -1(3) . . . . ?
C8A C9A C10A C11A 1(3) . . . . ?
C9A C10A C11A C12A 1(3) . . . . ?
C10A C11A C12A C7A -2(3) . . . . ?
C8A C7A C12A C11A 1(3) . . . . ?
C5A C7A C12A C11A -177.7(17) . . . . ?
C6A N2A C13A C18A -102.6(19) . . . . ?
Ni1A N2A C13A C18A 80.7(19) . . . . ?
C6A N2A C13A C14A 80(2) . . . . ?
Ni1A N2A C13A C14A -97.0(17) . . . . ?
C18A C13A C14A C15A -2(3) . . . . ?
N2A C13A C14A C15A 175.2(16) . . . . ?
C18A C13A C14A C19A 176.2(17) . . . . ?
N2A C13A C14A C19A -6(2) . . . . ?
C13A C14A C15A C16A -1(3) . . . . ?
C19A C14A C15A C16A -179.6(17) . . . . ?
C14A C15A C16A C17A 4(3) . . . . ?
C15A C16A C17A C18A -3(3) . . . . ?
C14A C13A C18A C17A 3(3) . . . . ?
N2A C13A C18A C17A -174.8(16) . . . . ?
C14A C13A C18A C20A -175.9(16) . . . . ?
N2A C13A C18A C20A 6(3) . . . . ?
C16A C17A C18A C13A 0(3) . . . . ?
C16A C17A C18A C20A 178.8(17) . . . . ?
C26A C21A C22A C23A -2(2) . . . . ?
Ni1A C21A C22A C23A -171.8(12) . . . . ?
C21A C22A C23A C24A 0(3) . . . . ?
C22A C23A C24A C25A 3(2) . . . . ?
C23A C24A C25A C26A -3(2) . . . . ?
C24A C25A C26A C21A 1(2) . . . . ?
C22A C21A C26A C25A 2(2) . . . . ?
Ni1A C21A C26A C25A 173.3(13) . . . . ?
C33A P1A C27A C28A -28.9(15) . . . . ?
C39A P1A C27A C28A -131.9(14) . . . . ?
Ni1A P1A C27A C28A 90.7(14) . . . . ?
C33A P1A C27A C32A 157.5(12) . . . . ?
C39A P1A C27A C32A 54.5(15) . . . . ?
Ni1A P1A C27A C32A -83.0(13) . . . . ?
C32A C27A C28A C29A 2(2) . . . . ?
P1A C27A C28A C29A -171.5(12) . . . . ?
C27A C28A C29A C30A -1(2) . . . . ?
C28A C29A C30A C31A 1(3) . . . . ?
C29A C30A C31A C32A -2(3) . . . . ?
C30A C31A C32A C27A 3(3) . . . . ?
C28A C27A C32A C31A -3(2) . . . . ?
P1A C27A C32A C31A 171.2(13) . . . . ?
C27A P1A C33A C38A 136.2(13) . . . . ?
C39A P1A C33A C38A -113.4(14) . . . . ?
Ni1A P1A C33A C38A 10.6(14) . . . . ?
C27A P1A C33A C34A -52.4(15) . . . . ?
C39A P1A C33A C34A 58.0(16) . . . . ?
Ni1A P1A C33A C34A -178.0(13) . . . . ?
C38A C33A C34A C35A -3(3) . . . . ?
P1A C33A C34A C35A -174.2(14) . . . . ?
C33A C34A C35A C36A 1(3) . . . . ?
C34A C35A C36A C37A 1(3) . . . . ?
C35A C36A C37A C38A -2(3) . . . . ?
C34A C33A C38A C37A 2(2) . . . . ?
P1A C33A C38A C37A 173.7(12) . . . . ?
C36A C37A C38A C33A 0(2) . . . . ?
C27A P1A C39A C40A -176.0(14) . . . . ?
C33A P1A C39A C40A 75.3(15) . . . . ?
Ni1A P1A C39A C40A -39.7(16) . . . . ?
C27A P1A C39A C44A 14.6(16) . . . . ?
C33A P1A C39A C44A -94.2(15) . . . . ?
Ni1A P1A C39A C44A 150.8(12) . . . . ?
C44A C39A C40A C41A -3(3) . . . . ?
P1A C39A C40A C41A -172.1(13) . . . . ?
C39A C40A C41A C42A 1(3) . . . . ?
C40A C41A C42A C43A 1(3) . . . . ?
C41A C42A C43A C44A 0(3) . . . . ?
C42A C43A C44A C39A -2(3) . . . . ?
C40A C39A C44A C43A 3(3) . . . . ?
P1A C39A C44A C43A 172.5(14) . . . . ?
C5B N1B C2B C6B 169.8(14) . . . . ?
Ni1B N1B C2B C6B -12.6(17) . . . . ?
C5B N1B C2B C3B -1.2(19) . . . . ?
Ni1B N1B C2B C3B 176.4(12) . . . . ?
C6B C2B C3B C4B -168.4(19) . . . . ?
N1B C2B C3B C4B 0(2) . . . . ?
C2B C3B C4B C5B 1(2) . . . . ?
C2B N1B C5B C4B 1.7(17) . . . . ?
Ni1B N1B C5B C4B -174.4(14) . . . . ?
C2B N1B C5B C7B -172.3(15) . . . . ?
Ni1B N1B C5B C7B 12(3) . . . . ?
C3B C4B C5B N1B -2(2) . . . . ?
C3B C4B C5B C7B 172.1(17) . . . . ?
C13B N2B C6B C2B -173.1(15) . . . . ?
Ni1B N2B C6B C2B 8.3(19) . . . . ?
C3B C2B C6B N2B 170.9(19) . . . . ?
N1B C2B C6B N2B 3(2) . . . . ?
N1B C5B C7B C12B 32(2) . . . . ?
C4B C5B C7B C12B -141.3(17) . . . . ?
N1B C5B C7B C8B -151.5(16) . . . . ?
C4B C5B C7B C8B 36(2) . . . . ?
C12B C7B C8B C9B -3(3) . . . . ?
C5B C7B C8B C9B -179.6(16) . . . . ?
C7B C8B C9B C10B 2(3) . . . . ?
C8B C9B C10B C11B -1(3) . . . . ?
C9B C10B C11B C12B 1(3) . . . . ?
C10B C11B C12B C7B -2(3) . . . . ?
C8B C7B C12B C11B 3(2) . . . . ?
C5B C7B C12B C11B 179.6(14) . . . . ?
C6B N2B C13B C18B 103.8(18) . . . . ?
Ni1B N2B C13B C18B -78(2) . . . . ?
C6B N2B C13B C14B -82(2) . . . . ?
Ni1B N2B C13B C14B 96.1(17) . . . . ?
C18B C13B C14B C15B 2(2) . . . . ?
N2B C13B C14B C15B -172.2(15) . . . . ?
C18B C13B C14B C19B -179.2(17) . . . . ?
N2B C13B C14B C19B 7(3) . . . . ?
C13B C14B C15B C16B -1(3) . . . . ?
C19B C14B C15B C16B 179.7(17) . . . . ?
C14B C15B C16B C17B -2(3) . . . . ?
C15B C16B C17B C18B 5(3) . . . . ?
C14B C13B C18B C17B 1(2) . . . . ?
N2B C13B C18B C17B 174.9(15) . . . . ?
C14B C13B C18B C20B 175.3(16) . . . . ?
N2B C13B C18B C20B -11(2) . . . . ?
C16B C17B C18B C13B -4(3) . . . . ?
C16B C17B C18B C20B -178.8(17) . . . . ?
N1B Ni1B C21B C22B 37(3) . . . . ?
N2B Ni1B C21B C22B 107.1(11) . . . . ?
P1B Ni1B C21B C22B -99.9(11) . . . . ?
N1B Ni1B C21B C26B -134(2) . . . . ?
N2B Ni1B C21B C26B -63.9(14) . . . . ?
P1B Ni1B C21B C26B 89.1(13) . . . . ?
C26B C21B C22B C23B 2(2) . . . . ?
Ni1B C21B C22B C23B -170.1(12) . . . . ?
C21B C22B C23B C24B -2(2) . . . . ?
C22B C23B C24B C25B 1(2) . . . . ?
C23B C24B C25B C26B 0(3) . . . . ?
C24B C25B C26B C21B 1(2) . . . . ?
C22B C21B C26B C25B -2(2) . . . . ?
Ni1B C21B C26B C25B 169.4(12) . . . . ?
C39B P1B C27B C28B -52.3(15) . . . . ?
C33B P1B C27B C28B -152.3(13) . . . . ?
Ni1B P1B C27B C28B 86.4(14) . . . . ?
C39B P1B C27B C32B 139.4(13) . . . . ?
C33B P1B C27B C32B 39.5(14) . . . . ?
Ni1B P1B C27B C32B -81.8(13) . . . . ?
C32B C27B C28B C29B -3(2) . . . . ?
P1B C27B C28B C29B -171.7(12) . . . . ?
C27B C28B C29B C30B 2(2) . . . . ?
C28B C29B C30B C31B 1(2) . . . . ?
C29B C30B C31B C32B -3(2) . . . . ?
C30B C31B C32B C27B 1(2) . . . . ?
C28B C27B C32B C31B 2(2) . . . . ?
P1B C27B C32B C31B 170.3(13) . . . . ?
C39B P1B C33B C34B 113.8(13) . . . . ?
C27B P1B C33B C34B -140.2(13) . . . . ?
Ni1B P1B C33B C34B -12.1(14) . . . . ?
C39B P1B C33B C38B -62.1(15) . . . . ?
C27B P1B C33B C38B 44.0(15) . . . . ?
Ni1B P1B C33B C38B 172.0(12) . . . . ?
C38B C33B C34B C35B 3(3) . . . . ?
P1B C33B C34B C35B -172.6(13) . . . . ?
C33B C34B C35B C36B -3(3) . . . . ?
C34B C35B C36B C37B 2(3) . . . . ?
C35B C36B C37B C38B -2(3) . . . . ?
C36B C37B C38B C33B 2(3) . . . . ?
C34B C33B C38B C37B -3(3) . . . . ?
P1B C33B C38B C37B 172.7(13) . . . . ?
C27B P1B C39B C44B -11.7(17) . . . . ?
C33B P1B C39B C44B 95.1(16) . . . . ?
Ni1B P1B C39B C44B -149.2(13) . . . . ?
C27B P1B C39B C40B 175.4(12) . . . . ?
C33B P1B C39B C40B -77.8(13) . . . . ?
Ni1B P1B C39B C40B 37.9(14) . . . . ?
C44B C39B C40B C41B -2(2) . . . . ?
P1B C39B C40B C41B 171.9(13) . . . . ?
C39B C40B C41B C42B 0(3) . . . . ?
C40B C41B C42B C43B 2(3) . . . . ?
C41B C42B C43B C44B -2(3) . . . . ?
C40B C39B C44B C43B 2(2) . . . . ?
P1B C39B C44B C43B -171.1(13) . . . . ?
C42B C43B C44B C39B 0(3) . . . . ?
C1 C2 C3 C4 176(2) . . . . ?
C2 C3 C4 C5 167(3) . . . . ?
C3 C4 C5 C6 173(4) . . . . ?

_refine_diff_density_max         1.051
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.108

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

data_5
_database_code_depnum_ccdc_archive 'CCDC 1853553'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C49 H49 N2 Ni P'
_chemical_formula_sum            'C49 H49 N2 Ni P'
_chemical_melting_point          ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Orange
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         755.58

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_chemical_absolute_configuration ?

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

_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.
;

_cell_length_a                   40.613(4)
_cell_length_b                   11.4486(12)
_cell_length_c                   18.1713(18)
_cell_angle_alpha                90
_cell_angle_beta                 107.820(4)
_cell_angle_gamma                90
_cell_volume                     8043.6(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6364
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      21.97
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_F_000             3200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.558
_shelx_estimated_absorpt_T_min   0.873
_shelx_estimated_absorpt_T_max   0.897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.873
_exptl_absorpt_correction_T_max  0.897
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            58869
_diffrn_reflns_av_unetI/netI     0.0754
_diffrn_reflns_av_R_equivalents  0.0941
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.109
_diffrn_reflns_theta_max         25.651
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7578
_reflns_number_gt                5211
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0461P)²+12.5877P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7578
_refine_ls_number_parameters     484
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1190
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.13357(2) 0.19151(3) 0.12825(2) 0.01708(12) Uani 1 1 d . . . . .
P1 P 0.11663(2) 0.01145(7) 0.11159(5) 0.01792(19) Uani 1 1 d . . . . .
N1 N 0.17507(6) 0.1921(2) 0.09442(13) 0.0179(6) Uani 1 1 d . . . . .
N2 N 0.13210(6) 0.3584(2) 0.09918(14) 0.0189(6) Uani 1 1 d . . . . .
C2 C 0.17294(8) 0.2861(3) 0.04516(17) 0.0188(7) Uani 1 1 d . . . . .
C3 C 0.19766(8) 0.2767(3) 0.00639(18) 0.0230(8) Uani 1 1 d . . . . .
H3 H 0.201152 0.329062 -0.031114 0.028 Uiso 1 1 calc R U . . .
C4 C 0.21609(8) 0.1754(3) 0.03381(17) 0.0222(7) Uani 1 1 d . . . . .
H4 H 0.234677 0.144774 0.018276 0.027 Uiso 1 1 calc R U . . .
C5 C 0.20220(8) 0.1263(3) 0.08884(17) 0.0183(7) Uani 1 1 d . . . . .
C6 C 0.15007(8) 0.3752(3) 0.05149(17) 0.0195(7) Uani 1 1 d . . . . .
H6 H 0.147791 0.445078 0.022136 0.023 Uiso 1 1 calc R U . . .
C7 C 0.21627(8) 0.0251(3) 0.13841(17) 0.0182(7) Uani 1 1 d . . . . .
C8 C 0.23310(8) -0.0639(3) 0.11184(18) 0.0235(8) Uani 1 1 d . . . . .
H8 H 0.234902 -0.059171 0.061021 0.028 Uiso 1 1 calc R U . . .
C9 C 0.24724(9) -0.1590(3) 0.15756(19) 0.0280(8) Uani 1 1 d . . . . .
C10 C 0.24517(9) -0.1633(3) 0.23271(19) 0.0292(8) Uani 1 1 d . . . . .
H10 H 0.254856 -0.228139 0.264642 0.035 Uiso 1 1 calc R U . . .
C11 C 0.22933(9) -0.0752(3) 0.26196(18) 0.0256(8) Uani 1 1 d . . . . .
C12 C 0.21435(8) 0.0177(3) 0.21373(17) 0.0213(7) Uani 1 1 d . . . . .
H12 H 0.202626 0.076997 0.232418 0.026 Uiso 1 1 calc R U . . .
C13 C 0.26406(11) -0.2570(3) 0.1269(2) 0.0441(11) Uani 1 1 d . . . . .
H13A H 0.262294 -0.241334 0.072774 0.066 Uiso 1 1 calc R U . . .
H13B H 0.252348 -0.330669 0.130317 0.066 Uiso 1 1 calc R U . . .
H13C H 0.288482 -0.262616 0.157554 0.066 Uiso 1 1 calc R U . . .
C14 C 0.22879(10) -0.0813(3) 0.34472(19) 0.0350(9) Uani 1 1 d . . . . .
H14A H 0.222020 -0.159975 0.355621 0.053 Uiso 1 1 calc R U . . .
H14B H 0.212120 -0.024369 0.352456 0.053 Uiso 1 1 calc R U . . .
H14C H 0.251871 -0.063318 0.379698 0.053 Uiso 1 1 calc R U . . .
C15 C 0.11034(8) 0.4503(3) 0.11230(18) 0.0205(7) Uani 1 1 d . . . . .
C16 C 0.08050(8) 0.4863(3) 0.05423(19) 0.0240(8) Uani 1 1 d . . . . .
C17 C 0.05926(9) 0.5693(3) 0.0734(2) 0.0321(9) Uani 1 1 d . . . . .
H17 H 0.038678 0.593784 0.035281 0.039 Uiso 1 1 calc R U . . .
C18 C 0.06765(9) 0.6159(3) 0.1463(2) 0.0345(9) Uani 1 1 d . . . . .
H18 H 0.052711 0.671370 0.158464 0.041 Uiso 1 1 calc R U . . .
C19 C 0.09776(9) 0.5825(3) 0.2023(2) 0.0317(9) Uani 1 1 d . . . . .
H19 H 0.103464 0.616785 0.252231 0.038 Uiso 1 1 calc R U . . .
C20 C 0.11977(9) 0.4999(3) 0.18682(18) 0.0242(8) Uani 1 1 d . . . . .
C21 C 0.07090(9) 0.4398(3) -0.02833(19) 0.0304(8) Uani 1 1 d . . . . .
H21 H 0.085393 0.369322 -0.028670 0.037 Uiso 1 1 calc R U . . .
C22 C 0.15443(9) 0.4709(3) 0.24620(19) 0.0298(8) Uani 1 1 d . . . . .
H22 H 0.160056 0.388030 0.237390 0.036 Uiso 1 1 calc R U . . .
C23 C 0.03279(10) 0.4049(4) -0.0611(2) 0.0434(10) Uani 1 1 d . . . . .
H23A H 0.027059 0.348355 -0.026354 0.065 Uiso 1 1 calc R U . . .
H23B H 0.028712 0.369562 -0.112201 0.065 Uiso 1 1 calc R U . . .
H23C H 0.018211 0.474363 -0.065558 0.065 Uiso 1 1 calc R U . . .
C24 C 0.07880(11) 0.5317(4) -0.0816(2) 0.0495(11) Uani 1 1 d . . . . .
H24A H 0.064796 0.601572 -0.082032 0.074 Uiso 1 1 calc R U . . .
H24B H 0.073280 0.500182 -0.134106 0.074 Uiso 1 1 calc R U . . .
H24C H 0.103383 0.552287 -0.062765 0.074 Uiso 1 1 calc R U . . .
C25 C 0.18308(9) 0.5473(3) 0.2342(2) 0.0428(10) Uani 1 1 d . . . . .
H25A H 0.184381 0.535843 0.181757 0.064 Uiso 1 1 calc R U . . .
H25B H 0.205214 0.525654 0.271835 0.064 Uiso 1 1 calc R U . . .
H25C H 0.178061 0.629469 0.241432 0.064 Uiso 1 1 calc R U . . .
C26 C 0.15396(11) 0.4804(3) 0.3297(2) 0.0434(10) Uani 1 1 d . . . . .
H26A H 0.150079 0.561962 0.341334 0.065 Uiso 1 1 calc R U . . .
H26B H 0.176175 0.453822 0.364748 0.065 Uiso 1 1 calc R U . . .
H26C H 0.135307 0.431676 0.336743 0.065 Uiso 1 1 calc R U . . .
C27 C 0.09901(8) 0.2087(3) 0.17876(17) 0.0200(7) Uani 1 1 d . . . . .
C28 C 0.06487(8) 0.2467(3) 0.14653(18) 0.0220(8) Uani 1 1 d . . . . .
H28 H 0.056090 0.258984 0.092311 0.026 Uiso 1 1 calc R U . . .
C29 C 0.04353(9) 0.2669(3) 0.19225(19) 0.0268(8) Uani 1 1 d . . . . .
H29 H 0.020516 0.293475 0.169135 0.032 Uiso 1 1 calc R U . . .
C30 C 0.05558(9) 0.2485(3) 0.2706(2) 0.0324(9) Uani 1 1 d . . . . .
H30 H 0.040868 0.261159 0.301690 0.039 Uiso 1 1 calc R U . . .
C31 C 0.08920(9) 0.2116(3) 0.30399(19) 0.0304(9) Uani 1 1 d . . . . .
H31 H 0.097730 0.199349 0.358240 0.037 Uiso 1 1 calc R U . . .
C32 C 0.11051(8) 0.1923(3) 0.25872(18) 0.0238(7) Uani 1 1 d . . . . .
H32 H 0.133623 0.167258 0.282664 0.029 Uiso 1 1 calc R U . . .
C33 C 0.07486(8) -0.0025(3) 0.03649(17) 0.0207(7) Uani 1 1 d . . . . .
C34 C 0.05915(9) -0.1120(3) 0.02185(19) 0.0274(8) Uani 1 1 d . . . . .
H34 H 0.068798 -0.176049 0.054595 0.033 Uiso 1 1 calc R U . . .
C35 C 0.02954(9) -0.1279(3) -0.0402(2) 0.0341(9) Uani 1 1 d . . . . .
H35 H 0.018791 -0.202486 -0.049333 0.041 Uiso 1 1 calc R U . . .
C36 C 0.01557(9) -0.0357(3) -0.0889(2) 0.0338(9) Uani 1 1 d . . . . .
H36 H -0.004534 -0.047209 -0.131799 0.041 Uiso 1 1 calc R U . . .
C37 C 0.03087(9) 0.0728(3) -0.07503(19) 0.0310(9) Uani 1 1 d . . . . .
H37 H 0.021147 0.136413 -0.108149 0.037 Uiso 1 1 calc R U . . .
C38 C 0.06052(8) 0.0895(3) -0.01266(17) 0.0226(8) Uani 1 1 d . . . . .
H38 H 0.071029 0.164488 -0.003637 0.027 Uiso 1 1 calc R U . . .
C39 C 0.11067(8) -0.0645(3) 0.19516(18) 0.0205(7) Uani 1 1 d . . . . .
C40 C 0.07845(9) -0.0701(3) 0.20652(19) 0.0274(8) Uani 1 1 d . . . . .
H40 H 0.058649 -0.042466 0.167391 0.033 Uiso 1 1 calc R U . . .
C41 C 0.07484(10) -0.1155(3) 0.2743(2) 0.0350(9) Uani 1 1 d . . . . .
H41 H 0.052616 -0.119298 0.281271 0.042 Uiso 1 1 calc R U . . .
C42 C 0.10320(11) -0.1548(3) 0.3311(2) 0.0368(10) Uani 1 1 d . . . . .
H42 H 0.100604 -0.185632 0.377606 0.044 Uiso 1 1 calc R U . . .
C43 C 0.13558(10) -0.1501(3) 0.32148(19) 0.0326(9) Uani 1 1 d . . . . .
H43 H 0.155185 -0.177891 0.361076 0.039 Uiso 1 1 calc R U . . .
C44 C 0.13947(9) -0.1043(3) 0.25335(18) 0.0245(8) Uani 1 1 d . . . . .
H44 H 0.161762 -0.100396 0.246747 0.029 Uiso 1 1 calc R U . . .
C45 C 0.14022(8) -0.0889(3) 0.06731(17) 0.0196(7) Uani 1 1 d . . . . .
C46 C 0.14708(8) -0.0482(3) 0.00060(17) 0.0234(8) Uani 1 1 d . . . . .
H46 H 0.141472 0.029784 -0.016408 0.028 Uiso 1 1 calc R U . . .
C47 C 0.16209(9) -0.1224(3) -0.04045(19) 0.0308(9) Uani 1 1 d . . . . .
H47 H 0.166606 -0.094878 -0.085734 0.037 Uiso 1 1 calc R U . . .
C48 C 0.17045(10) -0.2351(3) -0.0162(2) 0.0361(9) Uani 1 1 d . . . . .
H48 H 0.180914 -0.285001 -0.044407 0.043 Uiso 1 1 calc R U . . .
C49 C 0.16363(10) -0.2759(3) 0.0491(2) 0.0346(9) Uani 1 1 d . . . . .
H49 H 0.169443 -0.354045 0.065679 0.042 Uiso 1 1 calc R U . . .
C50 C 0.14834(9) -0.2038(3) 0.09098(19) 0.0263(8) Uani 1 1 d . . . . .
H50 H 0.143448 -0.232859 0.135493 0.032 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 C27 1.908(3) . ?
Ni1 N1 1.963(3) . ?
Ni1 N2 1.979(3) . ?
Ni1 P1 2.1649(9) . ?
P1 C39 1.829(3) . ?
P1 C33 1.830(3) . ?
P1 C45 1.832(3) . ?
N1 C5 1.364(4) . ?
N1 C2 1.385(4) . ?
N2 C6 1.307(4) . ?
N2 C15 1.440(4) . ?
C2 C3 1.396(4) . ?
C2 C6 1.408(4) . ?
C3 C4 1.388(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.407(4) . ?
C4 H4 0.9500 . ?
C5 C7 1.471(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.393(4) . ?
C7 C12 1.397(4) . ?
C8 C9 1.384(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(5) . ?
C9 C13 1.506(5) . ?
C10 C11 1.387(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.394(4) . ?
C11 C14 1.512(4) . ?
C12 H12 0.9500 . ?
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 C16 1.403(4) . ?
C15 C20 1.409(4) . ?
C16 C17 1.397(5) . ?
C16 C21 1.526(5) . ?
C17 C18 1.372(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(5) . ?
C19 H19 0.9500 . ?
C20 C22 1.525(5) . ?
C21 C24 1.528(5) . ?
C21 C23 1.532(5) . ?
C21 H21 1.0000 . ?
C22 C25 1.523(5) . ?
C22 C26 1.528(5) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C32 1.396(4) . ?
C27 C28 1.399(4) . ?
C28 C29 1.391(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.373(5) . ?
C29 H29 0.9500 . ?
C30 C31 1.380(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.382(4) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C38 1.389(4) . ?
C33 C34 1.395(4) . ?
C34 C35 1.386(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.382(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.378(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.391(5) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 C40 1.387(5) . ?
C39 C44 1.392(4) . ?
C40 C41 1.385(5) . ?
C40 H40 0.9500 . ?
C41 C42 1.367(5) . ?
C41 H41 0.9500 . ?
C42 C43 1.380(5) . ?
C42 H42 0.9500 . ?
C43 C44 1.397(4) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
C45 C50 1.392(4) . ?
C45 C46 1.404(4) . ?
C46 C47 1.388(5) . ?
C46 H46 0.9500 . ?
C47 C48 1.372(5) . ?
C47 H47 0.9500 . ?
C48 C49 1.381(5) . ?
C48 H48 0.9500 . ?
C49 C50 1.391(5) . ?
C49 H49 0.9500 . ?
C50 H50 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C27 Ni1 N1 168.23(12) . . ?
C27 Ni1 N2 93.58(12) . . ?
N1 Ni1 N2 82.62(11) . . ?
C27 Ni1 P1 85.21(9) . . ?
N1 Ni1 P1 103.07(8) . . ?
N2 Ni1 P1 154.15(8) . . ?
C39 P1 C33 104.46(14) . . ?
C39 P1 C45 106.65(15) . . ?
C33 P1 C45 96.21(14) . . ?
C39 P1 Ni1 116.98(10) . . ?
C33 P1 Ni1 111.68(11) . . ?
C45 P1 Ni1 118.16(11) . . ?
C5 N1 C2 105.9(2) . . ?
C5 N1 Ni1 144.3(2) . . ?
C2 N1 Ni1 108.4(2) . . ?
C6 N2 C15 119.9(3) . . ?
C6 N2 Ni1 110.0(2) . . ?
C15 N2 Ni1 129.1(2) . . ?
N1 C2 C3 110.7(3) . . ?
N1 C2 C6 115.0(3) . . ?
C3 C2 C6 133.7(3) . . ?
C4 C3 C2 106.0(3) . . ?
C4 C3 H3 127.0 . . ?
C2 C3 H3 127.0 . . ?
C3 C4 C5 107.4(3) . . ?
C3 C4 H4 126.3 . . ?
C5 C4 H4 126.3 . . ?
N1 C5 C4 109.9(3) . . ?
N1 C5 C7 124.1(3) . . ?
C4 C5 C7 125.8(3) . . ?
N2 C6 C2 117.6(3) . . ?
N2 C6 H6 121.2 . . ?
C2 C6 H6 121.2 . . ?
C8 C7 C12 118.4(3) . . ?
C8 C7 C5 120.2(3) . . ?
C12 C7 C5 121.4(3) . . ?
C9 C8 C7 121.7(3) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 118.5(3) . . ?
C8 C9 C13 121.0(3) . . ?
C10 C9 C13 120.4(3) . . ?
C11 C10 C9 121.6(3) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 118.6(3) . . ?
C10 C11 C14 119.9(3) . . ?
C12 C11 C14 121.6(3) . . ?
C11 C12 C7 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 121.5(3) . . ?
C16 C15 N2 121.5(3) . . ?
C20 C15 N2 117.0(3) . . ?
C17 C16 C15 118.0(3) . . ?
C17 C16 C21 119.4(3) . . ?
C15 C16 C21 122.6(3) . . ?
C18 C17 C16 121.0(3) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 120.4(3) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C20 121.2(3) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C19 C20 C15 117.8(3) . . ?
C19 C20 C22 121.2(3) . . ?
C15 C20 C22 120.8(3) . . ?
C16 C21 C24 110.0(3) . . ?
C16 C21 C23 113.4(3) . . ?
C24 C21 C23 108.5(3) . . ?
C16 C21 H21 108.3 . . ?
C24 C21 H21 108.3 . . ?
C23 C21 H21 108.3 . . ?
C25 C22 C20 110.7(3) . . ?
C25 C22 C26 110.1(3) . . ?
C20 C22 C26 113.4(3) . . ?
C25 C22 H22 107.5 . . ?
C20 C22 H22 107.5 . . ?
C26 C22 H22 107.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C26 H26A 109.5 . . ?
C22 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C22 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C32 C27 C28 116.8(3) . . ?
C32 C27 Ni1 115.2(2) . . ?
C28 C27 Ni1 127.7(2) . . ?
C29 C28 C27 121.3(3) . . ?
C29 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C30 C29 C28 120.3(3) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C31 119.5(3) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C30 C31 C32 120.2(3) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C31 C32 C27 121.8(3) . . ?
C31 C32 H32 119.1 . . ?
C27 C32 H32 119.1 . . ?
C38 C33 C34 118.8(3) . . ?
C38 C33 P1 121.6(2) . . ?
C34 C33 P1 119.1(2) . . ?
C35 C34 C33 120.4(3) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C36 C35 C34 120.3(3) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C37 C36 C35 119.9(3) . . ?
C37 C36 H36 120.1 . . ?
C35 C36 H36 120.1 . . ?
C36 C37 C38 120.2(3) . . ?
C36 C37 H37 119.9 . . ?
C38 C37 H37 119.9 . . ?
C33 C38 C37 120.5(3) . . ?
C33 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?
C40 C39 C44 118.9(3) . . ?
C40 C39 P1 121.1(2) . . ?
C44 C39 P1 119.5(2) . . ?
C41 C40 C39 120.7(3) . . ?
C41 C40 H40 119.6 . . ?
C39 C40 H40 119.6 . . ?
C42 C41 C40 120.1(3) . . ?
C42 C41 H41 120.0 . . ?
C40 C41 H41 120.0 . . ?
C41 C42 C43 120.4(3) . . ?
C41 C42 H42 119.8 . . ?
C43 C42 H42 119.8 . . ?
C42 C43 C44 119.9(3) . . ?
C42 C43 H43 120.1 . . ?
C44 C43 H43 120.1 . . ?
C39 C44 C43 120.0(3) . . ?
C39 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C50 C45 C46 119.3(3) . . ?
C50 C45 P1 124.3(2) . . ?
C46 C45 P1 116.1(2) . . ?
C47 C46 C45 119.8(3) . . ?
C47 C46 H46 120.1 . . ?
C45 C46 H46 120.1 . . ?
C48 C47 C46 120.6(3) . . ?
C48 C47 H47 119.7 . . ?
C46 C47 H47 119.7 . . ?
C47 C48 C49 119.9(3) . . ?
C47 C48 H48 120.0 . . ?
C49 C48 H48 120.0 . . ?
C48 C49 C50 120.7(3) . . ?
C48 C49 H49 119.7 . . ?
C50 C49 H49 119.7 . . ?
C49 C50 C45 119.7(3) . . ?
C49 C50 H50 120.2 . . ?
C45 C50 H50 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
C5 N1 C2 C3 2.5(3) . . . . ?
Ni1 N1 C2 C3 -167.1(2) . . . . ?
C5 N1 C2 C6 -170.2(3) . . . . ?
Ni1 N1 C2 C6 20.2(3) . . . . ?
N1 C2 C3 C4 -1.3(4) . . . . ?
C6 C2 C3 C4 169.4(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C2 N1 C5 C4 -2.7(3) . . . . ?
Ni1 N1 C5 C4 160.3(3) . . . . ?
C2 N1 C5 C7 172.5(3) . . . . ?
Ni1 N1 C5 C7 -24.5(5) . . . . ?
C3 C4 C5 N1 1.9(4) . . . . ?
C3 C4 C5 C7 -173.1(3) . . . . ?
C15 N2 C6 C2 175.2(3) . . . . ?
Ni1 N2 C6 C2 -15.2(3) . . . . ?
N1 C2 C6 N2 -3.4(4) . . . . ?
C3 C2 C6 N2 -173.9(3) . . . . ?
N1 C5 C7 C8 153.6(3) . . . . ?
C4 C5 C7 C8 -32.0(5) . . . . ?
N1 C5 C7 C12 -28.9(4) . . . . ?
C4 C5 C7 C12 145.5(3) . . . . ?
C12 C7 C8 C9 1.0(5) . . . . ?
C5 C7 C8 C9 178.7(3) . . . . ?
C7 C8 C9 C10 -1.6(5) . . . . ?
C7 C8 C9 C13 177.5(3) . . . . ?
C8 C9 C10 C11 0.2(5) . . . . ?
C13 C9 C10 C11 -178.9(3) . . . . ?
C9 C10 C11 C12 1.8(5) . . . . ?
C9 C10 C11 C14 -177.8(3) . . . . ?
C10 C11 C12 C7 -2.5(5) . . . . ?
C14 C11 C12 C7 177.2(3) . . . . ?
C8 C7 C12 C11 1.1(5) . . . . ?
C5 C7 C12 C11 -176.5(3) . . . . ?
C6 N2 C15 C16 68.4(4) . . . . ?
Ni1 N2 C15 C16 -98.9(3) . . . . ?
C6 N2 C15 C20 -113.6(3) . . . . ?
Ni1 N2 C15 C20 79.1(3) . . . . ?
C20 C15 C16 C17 -3.1(5) . . . . ?
N2 C15 C16 C17 174.9(3) . . . . ?
C20 C15 C16 C21 176.0(3) . . . . ?
N2 C15 C16 C21 -6.1(5) . . . . ?
C15 C16 C17 C18 1.2(5) . . . . ?
C21 C16 C17 C18 -177.8(3) . . . . ?
C16 C17 C18 C19 0.9(5) . . . . ?
C17 C18 C19 C20 -1.3(5) . . . . ?
C18 C19 C20 C15 -0.5(5) . . . . ?
C18 C19 C20 C22 174.7(3) . . . . ?
C16 C15 C20 C19 2.7(5) . . . . ?
N2 C15 C20 C19 -175.3(3) . . . . ?
C16 C15 C20 C22 -172.5(3) . . . . ?
N2 C15 C20 C22 9.5(4) . . . . ?
C17 C16 C21 C24 74.9(4) . . . . ?
C15 C16 C21 C24 -104.1(4) . . . . ?
C17 C16 C21 C23 -46.8(4) . . . . ?
C15 C16 C21 C23 134.2(3) . . . . ?
C19 C20 C22 C25 -91.6(4) . . . . ?
C15 C20 C22 C25 83.4(4) . . . . ?
C19 C20 C22 C26 32.7(4) . . . . ?
C15 C20 C22 C26 -152.3(3) . . . . ?
C32 C27 C28 C29 -0.1(5) . . . . ?
Ni1 C27 C28 C29 -173.1(2) . . . . ?
C27 C28 C29 C30 -0.7(5) . . . . ?
C28 C29 C30 C31 1.0(5) . . . . ?
C29 C30 C31 C32 -0.5(5) . . . . ?
C30 C31 C32 C27 -0.3(5) . . . . ?
C28 C27 C32 C31 0.6(5) . . . . ?
Ni1 C27 C32 C31 174.4(3) . . . . ?
C39 P1 C33 C38 139.6(3) . . . . ?
C45 P1 C33 C38 -111.4(3) . . . . ?
Ni1 P1 C33 C38 12.2(3) . . . . ?
C39 P1 C33 C34 -48.6(3) . . . . ?
C45 P1 C33 C34 60.4(3) . . . . ?
Ni1 P1 C33 C34 -176.0(2) . . . . ?
C38 C33 C34 C35 -0.7(5) . . . . ?
P1 C33 C34 C35 -172.7(3) . . . . ?
C33 C34 C35 C36 1.0(5) . . . . ?
C34 C35 C36 C37 -0.9(6) . . . . ?
C35 C36 C37 C38 0.6(5) . . . . ?
C34 C33 C38 C37 0.5(5) . . . . ?
P1 C33 C38 C37 172.3(2) . . . . ?
C36 C37 C38 C33 -0.4(5) . . . . ?
C33 P1 C39 C40 -29.3(3) . . . . ?
C45 P1 C39 C40 -130.5(3) . . . . ?
Ni1 P1 C39 C40 94.7(3) . . . . ?
C33 P1 C39 C44 159.0(3) . . . . ?
C45 P1 C39 C44 57.9(3) . . . . ?
Ni1 P1 C39 C44 -77.0(3) . . . . ?
C44 C39 C40 C41 -0.6(5) . . . . ?
P1 C39 C40 C41 -172.3(3) . . . . ?
C39 C40 C41 C42 0.4(5) . . . . ?
C40 C41 C42 C43 -0.2(6) . . . . ?
C41 C42 C43 C44 0.3(5) . . . . ?
C40 C39 C44 C43 0.7(5) . . . . ?
P1 C39 C44 C43 172.5(2) . . . . ?
C42 C43 C44 C39 -0.5(5) . . . . ?
C39 P1 C45 C50 5.6(3) . . . . ?
C33 P1 C45 C50 -101.6(3) . . . . ?
Ni1 P1 C45 C50 139.8(2) . . . . ?
C39 P1 C45 C46 178.9(2) . . . . ?
C33 P1 C45 C46 71.8(3) . . . . ?
Ni1 P1 C45 C46 -46.9(3) . . . . ?
C50 C45 C46 C47 -0.6(5) . . . . ?
P1 C45 C46 C47 -174.3(2) . . . . ?
C45 C46 C47 C48 -0.3(5) . . . . ?
C46 C47 C48 C49 0.6(5) . . . . ?
C47 C48 C49 C50 0.0(6) . . . . ?
C48 C49 C50 C45 -0.8(5) . . . . ?
C46 C45 C50 C49 1.1(5) . . . . ?
P1 C45 C50 C49 174.3(3) . . . . ?

_refine_diff_density_max         0.527
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.073


####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1853552'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2018-09-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C45 H41 N2 Ni P'
_chemical_formula_sum            'C45 H41 N2 Ni P'
_chemical_melting_point          ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         699.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_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.
;

_cell_length_a                   11.9364(3)
_cell_length_b                   32.1736(9)
_cell_length_c                   10.3382(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.6030(10)
_cell_angle_gamma                90
_cell_volume                     3762.81(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9932
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.74
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_F_000             1472
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.591
_shelx_estimated_absorpt_T_min   0.852
_shelx_estimated_absorpt_T_max   0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_T_max  0.881
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            83151
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.201
_diffrn_reflns_theta_max         28.037
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9051
_reflns_number_gt                7370
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  enCIFer
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0427P)²+2.5276P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9051
_refine_ls_number_parameters     446
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.044
_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 0.40646(2) 0.12697(2) 0.53356(2) 0.01365(7) Uani 1 1 d . . . . .
P1 P 0.41281(4) 0.12076(2) 0.74441(5) 0.01469(10) Uani 1 1 d . . . . .
N1 N 0.56993(12) 0.13636(4) 0.54177(15) 0.0156(3) Uani 1 1 d . . . . .
N2 N 0.39394(13) 0.10261(5) 0.35292(15) 0.0171(3) Uani 1 1 d . . . . .
C2 C 0.59663(15) 0.11263(6) 0.44408(18) 0.0175(3) Uani 1 1 d . . . . .
C3 C 0.71737(16) 0.11507(6) 0.4605(2) 0.0212(4) Uani 1 1 d . . . . .
H3 H 0.758209 0.101384 0.407446 0.025 Uiso 1 1 calc R U . . .
C4 C 0.76541(16) 0.14167(6) 0.57034(19) 0.0210(4) Uani 1 1 d . . . . .
H4 H 0.846085 0.149539 0.607213 0.025 Uiso 1 1 calc R U . . .
C5 C 0.67250(15) 0.15473(5) 0.61667(18) 0.0162(3) Uani 1 1 d . . . . .
C6 C 0.49886(15) 0.09551(5) 0.34355(18) 0.0181(4) Uani 1 1 d . . . . .
H6 H 0.508668 0.079305 0.271108 0.022 Uiso 1 1 calc R U . . .
C7 C 0.67931(15) 0.18795(5) 0.71643(18) 0.0173(3) Uani 1 1 d . . . . .
C8 C 0.77999(16) 0.19256(6) 0.83007(19) 0.0217(4) Uani 1 1 d . . . . .
H8 H 0.843036 0.173241 0.844785 0.026 Uiso 1 1 calc R U . . .
C9 C 0.78974(19) 0.22490(6) 0.9222(2) 0.0279(4) Uani 1 1 d . . . . .
C10 C 0.69873(19) 0.25361(6) 0.8972(2) 0.0296(5) Uani 1 1 d . . . . .
H10 H 0.705366 0.276023 0.958990 0.036 Uiso 1 1 calc R U . . .
C11 C 0.59799(18) 0.25040(6) 0.7838(2) 0.0250(4) Uani 1 1 d . . . . .
C12 C 0.58832(16) 0.21707(6) 0.69460(19) 0.0207(4) Uani 1 1 d . . . . .
H12 H 0.518974 0.214129 0.618042 0.025 Uiso 1 1 calc R U . . .
C13 C 0.8956(2) 0.22814(8) 1.0496(2) 0.0415(6) Uani 1 1 d . . . . .
H13A H 0.917418 0.257422 1.068155 0.062 Uiso 1 1 calc R U . . .
H13B H 0.962100 0.212848 1.036359 0.062 Uiso 1 1 calc R U . . .
H13C H 0.875938 0.216251 1.126937 0.062 Uiso 1 1 calc R U . . .
C14 C 0.5015(2) 0.28265(6) 0.7581(3) 0.0354(5) Uani 1 1 d . . . . .
H14A H 0.465823 0.281499 0.831227 0.053 Uiso 1 1 calc R U . . .
H14B H 0.440908 0.277062 0.670299 0.053 Uiso 1 1 calc R U . . .
H14C H 0.535191 0.310327 0.756022 0.053 Uiso 1 1 calc R U . . .
C15 C 0.29304(15) 0.08455(6) 0.25407(18) 0.0179(4) Uani 1 1 d . . . . .
C16 C 0.27609(16) 0.04145(6) 0.24847(19) 0.0213(4) Uani 1 1 d . . . . .
C17 C 0.17052(18) 0.02604(7) 0.1585(2) 0.0296(5) Uani 1 1 d . . . . .
H17 H 0.156742 -0.003090 0.154035 0.036 Uiso 1 1 calc R U . . .
C18 C 0.08636(18) 0.05192(7) 0.0767(2) 0.0332(5) Uani 1 1 d . . . . .
H18 H 0.014754 0.040727 0.017293 0.040 Uiso 1 1 calc R U . . .
C19 C 0.10565(17) 0.09442(7) 0.0805(2) 0.0276(4) Uani 1 1 d . . . . .
H19 H 0.047574 0.112200 0.022494 0.033 Uiso 1 1 calc R U . . .
C20 C 0.20904(16) 0.11129(6) 0.16842(19) 0.0212(4) Uani 1 1 d . . . . .
C21 C 0.36609(18) 0.01119(6) 0.3340(2) 0.0272(4) Uani 1 1 d . . . . .
H21A H 0.413709 0.000191 0.280139 0.041 Uiso 1 1 calc R U . . .
H21B H 0.325326 -0.011747 0.362600 0.041 Uiso 1 1 calc R U . . .
H21C H 0.417680 0.025473 0.414842 0.041 Uiso 1 1 calc R U . . .
C22 C 0.23098(19) 0.15736(6) 0.1689(2) 0.0283(4) Uani 1 1 d . . . . .
H22A H 0.281155 0.163433 0.112452 0.042 Uiso 1 1 calc R U . . .
H22B H 0.270656 0.166679 0.262625 0.042 Uiso 1 1 calc R U . . .
H22C H 0.155416 0.171960 0.131917 0.042 Uiso 1 1 calc R U . . .
C23 C 0.24051(15) 0.13196(6) 0.49512(17) 0.0169(3) Uani 1 1 d . . . . .
C24 C 0.15125(16) 0.10209(6) 0.45547(19) 0.0224(4) Uani 1 1 d . . . . .
H24 H 0.171651 0.073507 0.457373 0.027 Uiso 1 1 calc R U . . .
C25 C 0.03262(17) 0.11368(8) 0.4131(2) 0.0328(5) Uani 1 1 d . . . . .
H25 H -0.027009 0.092959 0.385924 0.039 Uiso 1 1 calc R U . . .
C26 C 0.00111(18) 0.15482(8) 0.4104(2) 0.0374(6) Uani 1 1 d . . . . .
H26 H -0.079944 0.162544 0.381151 0.045 Uiso 1 1 calc R U . . .
C27 C 0.08769(19) 0.18481(7) 0.4503(2) 0.0335(5) Uani 1 1 d . . . . .
H27 H 0.066303 0.213300 0.448513 0.040 Uiso 1 1 calc R U . . .
C28 C 0.20638(17) 0.17349(6) 0.49323(19) 0.0229(4) Uani 1 1 d . . . . .
H28 H 0.265272 0.194425 0.521785 0.028 Uiso 1 1 calc R U . . .
C29 C 0.31213(16) 0.15353(6) 0.79953(18) 0.0181(4) Uani 1 1 d . . . . .
C30 C 0.20080(16) 0.13861(6) 0.79232(19) 0.0224(4) Uani 1 1 d . . . . .
H30 H 0.184057 0.109770 0.778958 0.027 Uiso 1 1 calc R U . . .
C31 C 0.11412(18) 0.16567(7) 0.8045(2) 0.0298(5) Uani 1 1 d . . . . .
H31 H 0.038184 0.155317 0.798958 0.036 Uiso 1 1 calc R U . . .
C32 C 0.1379(2) 0.20741(7) 0.8247(2) 0.0359(5) Uani 1 1 d . . . . .
H32 H 0.078076 0.225937 0.831513 0.043 Uiso 1 1 calc R U . . .
C33 C 0.2485(2) 0.22236(7) 0.8351(2) 0.0357(5) Uani 1 1 d . . . . .
H33 H 0.265207 0.251120 0.851116 0.043 Uiso 1 1 calc R U . . .
C34 C 0.33581(19) 0.19569(6) 0.8223(2) 0.0258(4) Uani 1 1 d . . . . .
H34 H 0.411783 0.206258 0.829013 0.031 Uiso 1 1 calc R U . . .
C35 C 0.37247(15) 0.06762(5) 0.77363(18) 0.0173(3) Uani 1 1 d . . . . .
C36 C 0.36766(18) 0.05500(6) 0.9009(2) 0.0268(4) Uani 1 1 d . . . . .
H36 H 0.378814 0.074789 0.972080 0.032 Uiso 1 1 calc R U . . .
C37 C 0.3467(2) 0.01375(7) 0.9239(2) 0.0329(5) Uani 1 1 d . . . . .
H37 H 0.343323 0.005367 1.010648 0.039 Uiso 1 1 calc R U . . .
C38 C 0.3307(2) -0.01520(6) 0.8210(3) 0.0341(5) Uani 1 1 d . . . . .
H38 H 0.317353 -0.043542 0.837379 0.041 Uiso 1 1 calc R U . . .
C39 C 0.3341(2) -0.00303(6) 0.6949(2) 0.0344(5) Uani 1 1 d . . . . .
H39 H 0.322046 -0.022925 0.623893 0.041 Uiso 1 1 calc R U . . .
C40 C 0.35497(17) 0.03823(6) 0.6711(2) 0.0237(4) Uani 1 1 d . . . . .
H40 H 0.357314 0.046412 0.583721 0.028 Uiso 1 1 calc R U . . .
C41 C 0.55725(15) 0.12284(6) 0.87807(18) 0.0187(4) Uani 1 1 d . . . . .
C42 C 0.58082(17) 0.14542(7) 0.9981(2) 0.0259(4) Uani 1 1 d . . . . .
H42 H 0.520968 0.162268 1.013504 0.031 Uiso 1 1 calc R U . . .
C43 C 0.69249(19) 0.14338(7) 1.0960(2) 0.0325(5) Uani 1 1 d . . . . .
H43 H 0.708753 0.159102 1.177752 0.039 Uiso 1 1 calc R U . . .
C44 C 0.77942(19) 0.11864(7) 1.0749(2) 0.0325(5) Uani 1 1 d . . . . .
H44 H 0.855433 0.117366 1.141773 0.039 Uiso 1 1 calc R U . . .
C45 C 0.75551(17) 0.09571(6) 0.9561(2) 0.0279(4) Uani 1 1 d . . . . .
H45 H 0.815085 0.078413 0.942013 0.033 Uiso 1 1 calc R U . . .
C46 C 0.64567(16) 0.09776(6) 0.8576(2) 0.0223(4) Uani 1 1 d . . . . .
H46 H 0.630217 0.082086 0.775925 0.027 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 C23 1.8988(17) . ?
Ni1 N1 1.9494(14) . ?
Ni1 N2 1.9864(15) . ?
Ni1 P1 2.1660(5) . ?
P1 C29 1.8215(18) . ?
P1 C35 1.8272(18) . ?
P1 C41 1.8348(18) . ?
N1 C5 1.358(2) . ?
N1 C2 1.382(2) . ?
N2 C6 1.307(2) . ?
N2 C15 1.431(2) . ?
C2 C3 1.399(2) . ?
C2 C6 1.404(2) . ?
C3 C4 1.391(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.405(2) . ?
C4 H4 0.9500 . ?
C5 C7 1.469(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.395(3) . ?
C7 C12 1.397(3) . ?
C8 C9 1.390(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(3) . ?
C9 C13 1.510(3) . ?
C10 C11 1.390(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(3) . ?
C11 C14 1.509(3) . ?
C12 H12 0.9500 . ?
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 C20 1.401(3) . ?
C15 C16 1.400(3) . ?
C16 C17 1.397(3) . ?
C16 C21 1.509(3) . ?
C17 C18 1.370(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(3) . ?
C19 H19 0.9500 . ?
C20 C22 1.505(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C28 1.395(3) . ?
C23 C24 1.396(3) . ?
C24 C25 1.393(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.374(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.377(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.391(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C34 1.390(3) . ?
C29 C30 1.392(3) . ?
C30 C31 1.388(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.375(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.376(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.389(3) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 C40 1.385(3) . ?
C35 C36 1.395(3) . ?
C36 C37 1.385(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.381(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.373(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.387(3) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 C42 1.387(3) . ?
C41 C46 1.397(3) . ?
C42 C43 1.395(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.379(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.383(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.381(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C23 Ni1 N1 163.51(7) . . ?
C23 Ni1 N2 94.36(7) . . ?
N1 Ni1 N2 82.89(6) . . ?
C23 Ni1 P1 85.28(5) . . ?
N1 Ni1 P1 104.91(5) . . ?
N2 Ni1 P1 151.37(5) . . ?
C29 P1 C35 104.77(8) . . ?
C29 P1 C41 107.36(8) . . ?
C35 P1 C41 98.25(8) . . ?
C29 P1 Ni1 116.53(6) . . ?
C35 P1 Ni1 109.04(6) . . ?
C41 P1 Ni1 118.51(6) . . ?
C5 N1 C2 106.32(14) . . ?
C5 N1 Ni1 143.17(12) . . ?
C2 N1 Ni1 110.09(11) . . ?
C6 N2 C15 118.96(15) . . ?
C6 N2 Ni1 110.62(12) . . ?
C15 N2 Ni1 128.72(11) . . ?
N1 C2 C3 110.45(15) . . ?
N1 C2 C6 115.25(15) . . ?
C3 C2 C6 133.85(17) . . ?
C4 C3 C2 105.90(16) . . ?
C4 C3 H3 127.1 . . ?
C2 C3 H3 127.1 . . ?
C3 C4 C5 107.32(16) . . ?
C3 C4 H4 126.3 . . ?
C5 C4 H4 126.3 . . ?
N1 C5 C4 109.97(15) . . ?
N1 C5 C7 123.70(15) . . ?
C4 C5 C7 125.72(16) . . ?
N2 C6 C2 117.81(16) . . ?
N2 C6 H6 121.1 . . ?
C2 C6 H6 121.1 . . ?
C8 C7 C12 118.78(17) . . ?
C8 C7 C5 120.55(16) . . ?
C12 C7 C5 120.55(16) . . ?
C9 C8 C7 121.18(18) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C10 C9 C8 118.79(19) . . ?
C10 C9 C13 120.32(19) . . ?
C8 C9 C13 120.9(2) . . ?
C9 C10 C11 121.59(18) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C10 C11 C12 118.79(19) . . ?
C10 C11 C14 120.24(19) . . ?
C12 C11 C14 120.97(19) . . ?
C11 C12 C7 120.84(18) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 121.15(17) . . ?
C20 C15 N2 118.13(16) . . ?
C16 C15 N2 120.64(16) . . ?
C17 C16 C15 117.84(18) . . ?
C17 C16 C21 118.91(18) . . ?
C15 C16 C21 123.25(17) . . ?
C18 C17 C16 121.57(19) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 120.00(19) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 120.64(19) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 118.75(18) . . ?
C19 C20 C22 120.31(18) . . ?
C15 C20 C22 120.93(17) . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C28 C23 C24 117.59(17) . . ?
C28 C23 Ni1 111.37(13) . . ?
C24 C23 Ni1 130.61(14) . . ?
C25 C24 C23 120.81(19) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C26 C25 C24 120.6(2) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C27 119.63(19) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C26 C27 C28 120.2(2) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C27 C28 C23 121.22(19) . . ?
C27 C28 H28 119.4 . . ?
C23 C28 H28 119.4 . . ?
C34 C29 C30 118.98(17) . . ?
C34 C29 P1 119.93(14) . . ?
C30 C29 P1 119.82(14) . . ?
C31 C30 C29 120.34(19) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C32 C31 C30 120.2(2) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C33 C32 C31 119.98(19) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C32 C33 C34 120.5(2) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 H33 119.8 . . ?
C33 C34 C29 120.1(2) . . ?
C33 C34 H34 120.0 . . ?
C29 C34 H34 120.0 . . ?
C40 C35 C36 118.76(17) . . ?
C40 C35 P1 119.69(14) . . ?
C36 C35 P1 121.36(14) . . ?
C37 C36 C35 120.31(19) . . ?
C37 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
C38 C37 C36 120.2(2) . . ?
C38 C37 H37 119.9 . . ?
C36 C37 H37 119.9 . . ?
C39 C38 C37 119.98(19) . . ?
C39 C38 H38 120.0 . . ?
C37 C38 H38 120.0 . . ?
C38 C39 C40 120.2(2) . . ?
C38 C39 H39 119.9 . . ?
C40 C39 H39 119.9 . . ?
C39 C40 C35 120.59(19) . . ?
C39 C40 H40 119.7 . . ?
C35 C40 H40 119.7 . . ?
C42 C41 C46 119.37(17) . . ?
C42 C41 P1 124.51(15) . . ?
C46 C41 P1 116.02(14) . . ?
C41 C42 C43 119.94(19) . . ?
C41 C42 H42 120.0 . . ?
C43 C42 H42 120.0 . . ?
C44 C43 C42 120.3(2) . . ?
C44 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
C43 C44 C45 119.75(19) . . ?
C43 C44 H44 120.1 . . ?
C45 C44 H44 120.1 . . ?
C46 C45 C44 120.5(2) . . ?
C46 C45 H45 119.7 . . ?
C44 C45 H45 119.7 . . ?
C45 C46 C41 120.10(19) . . ?
C45 C46 H46 120.0 . . ?
C41 C46 H46 120.0 . . ?

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
C5 N1 C2 C3 1.9(2) . . . . ?
Ni1 N1 C2 C3 -172.48(12) . . . . ?
C5 N1 C2 C6 -171.48(15) . . . . ?
Ni1 N1 C2 C6 14.17(19) . . . . ?
N1 C2 C3 C4 -0.9(2) . . . . ?
C6 C2 C3 C4 170.7(2) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C2 N1 C5 C4 -2.1(2) . . . . ?
Ni1 N1 C5 C4 169.04(16) . . . . ?
C2 N1 C5 C7 169.43(16) . . . . ?
Ni1 N1 C5 C7 -19.4(3) . . . . ?
C3 C4 C5 N1 1.6(2) . . . . ?
C3 C4 C5 C7 -169.75(17) . . . . ?
C15 N2 C6 C2 -178.21(16) . . . . ?
Ni1 N2 C6 C2 -11.8(2) . . . . ?
N1 C2 C6 N2 -1.5(2) . . . . ?
C3 C2 C6 N2 -172.9(2) . . . . ?
N1 C5 C7 C8 150.33(17) . . . . ?
C4 C5 C7 C8 -39.5(3) . . . . ?
N1 C5 C7 C12 -33.8(3) . . . . ?
C4 C5 C7 C12 136.38(19) . . . . ?
C12 C7 C8 C9 1.3(3) . . . . ?
C5 C7 C8 C9 177.23(17) . . . . ?
C7 C8 C9 C10 -2.0(3) . . . . ?
C7 C8 C9 C13 176.13(19) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
C13 C9 C10 C11 -177.2(2) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C9 C10 C11 C14 -178.84(19) . . . . ?
C10 C11 C12 C7 -1.6(3) . . . . ?
C14 C11 C12 C7 178.07(18) . . . . ?
C8 C7 C12 C11 0.6(3) . . . . ?
C5 C7 C12 C11 -175.36(17) . . . . ?
C6 N2 C15 C20 -116.30(19) . . . . ?
Ni1 N2 C15 C20 80.1(2) . . . . ?
C6 N2 C15 C16 67.0(2) . . . . ?
Ni1 N2 C15 C16 -96.62(19) . . . . ?
C20 C15 C16 C17 -2.5(3) . . . . ?
N2 C15 C16 C17 174.06(17) . . . . ?
C20 C15 C16 C21 177.26(18) . . . . ?
N2 C15 C16 C21 -6.2(3) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C21 C16 C17 C18 -178.9(2) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
C17 C18 C19 C20 -1.0(3) . . . . ?
C18 C19 C20 C15 -0.6(3) . . . . ?
C18 C19 C20 C22 178.1(2) . . . . ?
C16 C15 C20 C19 2.4(3) . . . . ?
N2 C15 C20 C19 -174.27(17) . . . . ?
C16 C15 C20 C22 -176.30(18) . . . . ?
N2 C15 C20 C22 7.0(3) . . . . ?
N1 Ni1 C23 C28 -36.1(3) . . . . ?
N2 Ni1 C23 C28 -115.71(14) . . . . ?
P1 Ni1 C23 C28 93.01(13) . . . . ?
N1 Ni1 C23 C24 136.1(2) . . . . ?
N2 Ni1 C23 C24 56.43(18) . . . . ?
P1 Ni1 C23 C24 -94.85(17) . . . . ?
C28 C23 C24 C25 1.2(3) . . . . ?
Ni1 C23 C24 C25 -170.51(15) . . . . ?
C23 C24 C25 C26 -0.4(3) . . . . ?
C24 C25 C26 C27 -0.2(3) . . . . ?
C25 C26 C27 C28 0.0(3) . . . . ?
C26 C27 C28 C23 0.9(3) . . . . ?
C24 C23 C28 C27 -1.5(3) . . . . ?
Ni1 C23 C28 C27 171.78(15) . . . . ?
C35 P1 C29 C34 164.58(15) . . . . ?
C41 P1 C29 C34 60.82(17) . . . . ?
Ni1 P1 C29 C34 -74.84(16) . . . . ?
C35 P1 C29 C30 -28.41(17) . . . . ?
C41 P1 C29 C30 -132.18(15) . . . . ?
Ni1 P1 C29 C30 92.17(15) . . . . ?
C34 C29 C30 C31 1.5(3) . . . . ?
P1 C29 C30 C31 -165.66(15) . . . . ?
C29 C30 C31 C32 -0.4(3) . . . . ?
C30 C31 C32 C33 -1.1(3) . . . . ?
C31 C32 C33 C34 1.4(3) . . . . ?
C32 C33 C34 C29 -0.4(3) . . . . ?
C30 C29 C34 C33 -1.1(3) . . . . ?
P1 C29 C34 C33 166.02(16) . . . . ?
C29 P1 C35 C40 131.32(15) . . . . ?
C41 P1 C35 C40 -118.19(16) . . . . ?
Ni1 P1 C35 C40 5.89(16) . . . . ?
C29 P1 C35 C36 -53.69(17) . . . . ?
C41 P1 C35 C36 56.80(17) . . . . ?
Ni1 P1 C35 C36 -179.12(14) . . . . ?
C40 C35 C36 C37 0.5(3) . . . . ?
P1 C35 C36 C37 -174.52(16) . . . . ?
C35 C36 C37 C38 0.2(3) . . . . ?
C36 C37 C38 C39 -0.8(3) . . . . ?
C37 C38 C39 C40 0.8(3) . . . . ?
C38 C39 C40 C35 -0.1(3) . . . . ?
C36 C35 C40 C39 -0.5(3) . . . . ?
P1 C35 C40 C39 174.58(16) . . . . ?
C29 P1 C41 C42 0.53(19) . . . . ?
C35 P1 C41 C42 -107.85(17) . . . . ?
Ni1 P1 C41 C42 135.15(15) . . . . ?
C29 P1 C41 C46 176.82(14) . . . . ?
C35 P1 C41 C46 68.44(15) . . . . ?
Ni1 P1 C41 C46 -48.55(16) . . . . ?
C46 C41 C42 C43 0.9(3) . . . . ?
P1 C41 C42 C43 177.05(16) . . . . ?
C41 C42 C43 C44 -0.7(3) . . . . ?
C42 C43 C44 C45 -0.1(3) . . . . ?
C43 C44 C45 C46 0.8(3) . . . . ?
C44 C45 C46 C41 -0.6(3) . . . . ?
C42 C41 C46 C45 -0.3(3) . . . . ?
P1 C41 C46 C45 -176.76(15) . . . . ?

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.066


