# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# 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_job
_database_code_depnum_ccdc_archive 'CCDC 1055620'
_audit_update_record             
;
2015-03-23 deposited with the CCDC.
2015-07-10 downloaded from the CCDC.
;

_audit_creation_date             2009-04-24T09:28:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H21 N4 O, F6 P'
_chemical_formula_sum            'C13 H21 F6 N4 O P'
_chemical_formula_weight         394.31
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3802(11)
_cell_length_b                   8.3070(14)
_cell_length_c                   14.538(2)
_cell_angle_alpha                93.277(11)
_cell_angle_beta                 99.516(13)
_cell_angle_gamma                96.900(11)
_cell_volume                     870.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    18923
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.485
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 3 -11 0.112
14 1 -3 0.06
7 -6 19 0.029
-17 -1 3 0.074
1 17 1 0.072
0 -1 0 0.064
-3 1 16 0.053
3 -1 -10 0.108

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_T_max  0.971


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      0.26594E-2
_diffrn_orient_matrix_ub_12      0.100665
_diffrn_orient_matrix_ub_13      -0.347195E-1
_diffrn_orient_matrix_ub_21      -0.127566
_diffrn_orient_matrix_ub_22      0.132885E-1
_diffrn_orient_matrix_ub_23      0.113931E-1
_diffrn_orient_matrix_ub_31      0.543257E-1
_diffrn_orient_matrix_ub_32      0.67134E-1
_diffrn_orient_matrix_ub_33      0.596407E-1
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_number            15450
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.5
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             3980
_reflns_number_gt                3166
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0503P)²+0.1748P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3980
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0918
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.42
_refine_diff_density_rms         0.079

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1856(2) 0.92553(19) 0.42928(11) 0.0298(4) Uani 1 1 d . . .
H1A H 1.3036 0.8821 0.4447 0.045 Uiso 1 1 calc R . .
H1B H 1.1152 0.9103 0.4804 0.045 Uiso 1 1 calc R . .
H1C H 1.2095 1.0418 0.4205 0.045 Uiso 1 1 calc R . .
C2 C 1.0765(2) 0.83792(16) 0.34130(10) 0.0222(3) Uani 1 1 d . . .
C3 C 0.9046(2) 0.73906(17) 0.32783(11) 0.0255(3) Uani 1 1 d . . .
H3 H 0.8302 0.7139 0.3739 0.031 Uiso 1 1 calc R . .
C4 C 0.8657(2) 0.68624(17) 0.23466(11) 0.0235(3) Uani 1 1 d . . .
C5 C 0.7067(2) 0.5746(2) 0.17954(13) 0.0337(4) Uani 1 1 d . . .
H5A H 0.6443 0.6316 0.1288 0.05 Uiso 1 1 calc R . .
H5B H 0.619 0.5396 0.2205 0.05 Uiso 1 1 calc R . .
H5C H 0.7523 0.4793 0.1531 0.05 Uiso 1 1 calc R . .
N6 N 1.00927(16) 0.75575(13) 0.19629(8) 0.0189(3) Uani 1 1 d . . .
N7 N 1.14187(16) 0.84758(13) 0.26093(8) 0.0194(3) Uani 1 1 d . . .
C8 C 1.0473(2) 0.72695(16) 0.10217(10) 0.0206(3) Uani 1 1 d . . .
H8A H 1.0967 0.8311 0.08 0.025 Uiso 1 1 calc R . .
H8B H 0.9306 0.6838 0.0595 0.025 Uiso 1 1 calc R . .
C9 C 1.1860(2) 0.60730(16) 0.09958(10) 0.0211(3) Uani 1 1 d . . .
H9A H 1.2242 0.6012 0.0375 0.025 Uiso 1 1 calc R . .
H9B H 1.2976 0.6425 0.1476 0.025 Uiso 1 1 calc R . .
O10 O 1.09887(13) 0.45186(11) 0.11765(7) 0.0197(2) Uani 1 1 d . . .
C11 C 1.22837(19) 0.34561(16) 0.14956(10) 0.0204(3) Uani 1 1 d . . .
H11A H 1.3069 0.3924 0.2092 0.025 Uiso 1 1 calc R . .
H11B H 1.3096 0.33 0.1029 0.025 Uiso 1 1 calc R . .
C12 C 1.1218(2) 0.18510(16) 0.16366(10) 0.0206(3) Uani 1 1 d . . .
H12A H 1.0471 0.138 0.1031 0.025 Uiso 1 1 calc R . .
H12B H 1.2102 0.1088 0.1853 0.025 Uiso 1 1 calc R . .
N13 N 0.99807(16) 0.20302(13) 0.23267(8) 0.0182(3) Uani 1 1 d . . .
C14 C 0.84203(19) 0.10442(16) 0.23209(10) 0.0190(3) Uani 1 1 d . . .
H14 H 0.7934 0.0154 0.1874 0.023 Uiso 1 1 calc R . .
C15 C 1.0223(2) 0.31566(17) 0.30840(10) 0.0245(3) Uani 1 1 d . . .
H15 H 1.1225 0.4006 0.3261 0.029 Uiso 1 1 calc R . .
C16 C 0.8769(2) 0.28275(17) 0.35263(10) 0.0248(3) Uani 1 1 d . . .
H16 H 0.8556 0.3404 0.4073 0.03 Uiso 1 1 calc R . .
N17 N 0.76504(17) 0.15009(14) 0.30386(8) 0.0209(3) Uani 1 1 d . . .
C18 C 0.5928(2) 0.06795(19) 0.32793(11) 0.0284(3) Uani 1 1 d . . .
H18A H 0.5121 0.0165 0.2709 0.043 Uiso 1 1 calc R . .
H18B H 0.5291 0.1479 0.3578 0.043 Uiso 1 1 calc R . .
H18C H 0.6226 -0.0152 0.3711 0.043 Uiso 1 1 calc R . .
P1 P 0.5 0 0 0.01826(13) Uani 1 2 d S . .
F11 F 0.47107(13) -0.06526(11) 0.09871(6) 0.0330(2) Uani 1 1 d . . .
F12 F 0.42416(13) -0.17660(10) -0.05045(7) 0.0320(2) Uani 1 1 d . . .
F13 F 0.70820(12) -0.04633(11) 0.01681(6) 0.0305(2) Uani 1 1 d . . .
P2 P 0.5 0.5 0.5 0.02352(14) Uani 1 2 d S . .
F21 F 0.50850(14) 0.53973(13) 0.60999(7) 0.0394(3) Uani 1 1 d . . .
F22 F 0.28848(13) 0.53506(12) 0.48065(7) 0.0381(3) Uani 1 1 d . . .
F23 F 0.43228(15) 0.31303(11) 0.50985(8) 0.0447(3) Uani 1 1 d . . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.492(2) . ?
C1 H1A 0.98 . ?
C1 H1B 0.98 . ?
C1 H1C 0.98 . ?
C2 N7 1.3388(18) . ?
C2 C3 1.404(2) . ?
C3 C4 1.372(2) . ?
C3 H3 0.95 . ?
C4 N6 1.3609(18) . ?
C4 C5 1.491(2) . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
N6 N7 1.3628(17) . ?
N6 C8 1.4541(18) . ?
C8 C9 1.5131(19) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 O10 1.4300(15) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
O10 C11 1.4179(16) . ?
C11 C12 1.5069(18) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 N13 1.4770(17) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
N13 C14 1.3291(18) . ?
N13 C15 1.3773(19) . ?
C14 N17 1.3260(18) . ?
C14 H14 0.95 . ?
C15 C16 1.348(2) . ?
C15 H15 0.95 . ?
C16 N17 1.3775(19) . ?
C16 H16 0.95 . ?
N17 C18 1.4730(18) . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
P1 F12 1.5960(9) 2_655 ?
P1 F12 1.5960(9) . ?
P1 F11 1.6003(9) 2_655 ?
P1 F11 1.6004(9) . ?
P1 F13 1.6117(9) 2_655 ?
P1 F13 1.6117(9) . ?
P2 F23 1.5953(10) 2_666 ?
P2 F23 1.5953(10) . ?
P2 F21 1.6035(9) 2_666 ?
P2 F21 1.6035(9) . ?
P2 F22 1.6044(10) 2_666 ?
P2 F22 1.6045(10) . ?


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
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 . . ?
N7 C2 C3 110.97(13) . . ?
N7 C2 C1 120.09(13) . . ?
C3 C2 C1 128.94(13) . . ?
C4 C3 C2 106.03(13) . . ?
C4 C3 H3 127 . . ?
C2 C3 H3 127 . . ?
N6 C4 C3 106.04(13) . . ?
N6 C4 C5 122.94(14) . . ?
C3 C4 C5 131.01(14) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 N6 N7 112.41(12) . . ?
C4 N6 C8 128.68(12) . . ?
N7 N6 C8 118.35(11) . . ?
C2 N7 N6 104.52(11) . . ?
N6 C8 C9 111.18(11) . . ?
N6 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N6 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108 . . ?
O10 C9 C8 107.79(11) . . ?
O10 C9 H9A 110.1 . . ?
C8 C9 H9A 110.1 . . ?
O10 C9 H9B 110.1 . . ?
C8 C9 H9B 110.1 . . ?
H9A C9 H9B 108.5 . . ?
C11 O10 C9 112.70(10) . . ?
O10 C11 C12 108.10(11) . . ?
O10 C11 H11A 110.1 . . ?
C12 C11 H11A 110.1 . . ?
O10 C11 H11B 110.1 . . ?
C12 C11 H11B 110.1 . . ?
H11A C11 H11B 108.4 . . ?
N13 C12 C11 111.88(11) . . ?
N13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
N13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C14 N13 C15 108.22(12) . . ?
C14 N13 C12 123.69(12) . . ?
C15 N13 C12 128.05(12) . . ?
N17 C14 N13 109.16(12) . . ?
N17 C14 H14 125.4 . . ?
N13 C14 H14 125.4 . . ?
C16 C15 N13 107.11(13) . . ?
C16 C15 H15 126.4 . . ?
N13 C15 H15 126.4 . . ?
C15 C16 N17 107.34(13) . . ?
C15 C16 H16 126.3 . . ?
N17 C16 H16 126.3 . . ?
C14 N17 C16 108.16(12) . . ?
C14 N17 C18 125.18(13) . . ?
C16 N17 C18 126.63(12) . . ?
N17 C18 H18A 109.5 . . ?
N17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
F12 P1 F12 180 2_655 . ?
F12 P1 F11 90.16(5) 2_655 2_655 ?
F12 P1 F11 89.84(5) . 2_655 ?
F12 P1 F11 89.84(5) 2_655 . ?
F12 P1 F11 90.16(5) . . ?
F11 P1 F11 180.00(2) 2_655 . ?
F12 P1 F13 90.37(5) 2_655 2_655 ?
F12 P1 F13 89.63(5) . 2_655 ?
F11 P1 F13 89.89(5) 2_655 2_655 ?
F11 P1 F13 90.11(5) . 2_655 ?
F12 P1 F13 89.63(5) 2_655 . ?
F12 P1 F13 90.37(5) . . ?
F11 P1 F13 90.11(5) 2_655 . ?
F11 P1 F13 89.89(5) . . ?
F13 P1 F13 180 2_655 . ?
F23 P2 F23 180 2_666 . ?
F23 P2 F21 90.30(6) 2_666 2_666 ?
F23 P2 F21 89.70(6) . 2_666 ?
F23 P2 F21 89.70(6) 2_666 . ?
F23 P2 F21 90.30(6) . . ?
F21 P2 F21 180.00(11) 2_666 . ?
F23 P2 F22 90.00(6) 2_666 2_666 ?
F23 P2 F22 90.00(6) . 2_666 ?
F21 P2 F22 89.95(5) 2_666 2_666 ?
F21 P2 F22 90.05(5) . 2_666 ?
F23 P2 F22 90.00(6) 2_666 . ?
F23 P2 F22 90.00(6) . . ?
F21 P2 F22 90.05(5) 2_666 . ?
F21 P2 F22 89.95(5) . . ?
F22 P2 F22 179.999(17) 2_666 . ?


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
N7 C2 C3 C4 0.33(16) . . . . ?
C1 C2 C3 C4 -179.28(14) . . . . ?
C2 C3 C4 N6 -1.20(15) . . . . ?
C2 C3 C4 C5 177.87(15) . . . . ?
C3 C4 N6 N7 1.73(15) . . . . ?
C5 C4 N6 N7 -177.43(13) . . . . ?
C3 C4 N6 C8 172.83(13) . . . . ?
C5 C4 N6 C8 -6.3(2) . . . . ?
C3 C2 N7 N6 0.68(15) . . . . ?
C1 C2 N7 N6 -179.67(12) . . . . ?
C4 N6 N7 C2 -1.50(14) . . . . ?
C8 N6 N7 C2 -173.62(11) . . . . ?
C4 N6 C8 C9 -97.37(16) . . . . ?
N7 N6 C8 C9 73.28(14) . . . . ?
N6 C8 C9 O10 68.03(15) . . . . ?
C8 C9 O10 C11 -159.01(11) . . . . ?
C9 O10 C11 C12 -178.45(11) . . . . ?
O10 C11 C12 N13 -59.51(15) . . . . ?
C11 C12 N13 C14 152.13(13) . . . . ?
C11 C12 N13 C15 -30.1(2) . . . . ?
C15 N13 C14 N17 0.43(16) . . . . ?
C12 N13 C14 N17 178.57(12) . . . . ?
C14 N13 C15 C16 -0.34(16) . . . . ?
C12 N13 C15 C16 -178.38(13) . . . . ?
N13 C15 C16 N17 0.13(17) . . . . ?
N13 C14 N17 C16 -0.35(16) . . . . ?
N13 C14 N17 C18 -178.42(12) . . . . ?
C15 C16 N17 C14 0.13(17) . . . . ?
C15 C16 N17 C18 178.17(14) . . . . ?


####################################################################### 
# 
# 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_job
_database_code_depnum_ccdc_archive 'CCDC 1055623'
_audit_update_record             
;
2015-03-23 deposited with the CCDC.
2015-07-10 downloaded from the CCDC.
;

_audit_creation_date             2009-06-12T14:00:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H23 N4 O, F6 P'
_chemical_formula_sum            'C14 H23 F6 N4 O P'
_chemical_formula_weight         408.33
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.8869(4)
_cell_length_b                   8.5977(3)
_cell_length_c                   21.7613(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.160(2)
_cell_angle_gamma                90
_cell_volume                     1844.94(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3949
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.43
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.47
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_T_max  0.968


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_number            9900
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             4181
_reflns_number_gt                3579
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker SAINT'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0370P)²+0.9007P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4181
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.097
_refine_ls_wR_factor_gt          0.0913
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.056

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1000(2) 0.4564(2) 0.34161(9) 0.0373(5) Uani 1 1 d . . .
H1A H -0.173 0.5197 0.3568 0.056 Uiso 1 1 calc R . .
H1B H -0.0944 0.4752 0.2975 0.056 Uiso 1 1 calc R . .
H1C H -0.0137 0.4845 0.3638 0.056 Uiso 1 1 calc R . .
C2 C -0.12894(16) 0.28829(17) 0.35201(8) 0.0206(3) Uani 1 1 d . . .
C3 C -0.14751(15) 0.16722(18) 0.31068(7) 0.0192(3) Uani 1 1 d . . .
H3 H -0.147 0.1724 0.2671 0.023 Uiso 1 1 calc R . .
C4 C -0.16721(14) 0.03512(17) 0.34650(7) 0.0159(3) Uani 1 1 d . . .
C5 C -0.19095(17) -0.12877(18) 0.32505(8) 0.0230(3) Uani 1 1 d . . .
H5A H -0.117 -0.1952 0.3422 0.034 Uiso 1 1 calc R . .
H5B H -0.1941 -0.1322 0.28 0.034 Uiso 1 1 calc R . .
H5C H -0.2773 -0.1662 0.3389 0.034 Uiso 1 1 calc R . .
N6 N -0.16176(12) 0.06985(14) 0.40633(6) 0.0151(3) Uani 1 1 d . . .
N7 N -0.13814(12) 0.22677(14) 0.40855(6) 0.0161(3) Uani 1 1 d . . .
C8 C -0.13056(16) 0.30361(18) 0.46837(7) 0.0202(3) Uani 1 1 d . . .
H8A H -0.2102 0.273 0.4907 0.024 Uiso 1 1 calc R . .
H8B H -0.1345 0.4176 0.4621 0.024 Uiso 1 1 calc R . .
C9 C -0.00300(16) 0.26346(18) 0.50719(7) 0.0194(3) Uani 1 1 d . . .
H9A H -0.0082 0.3039 0.5495 0.023 Uiso 1 1 calc R . .
H9B H 0.0085 0.1492 0.5094 0.023 Uiso 1 1 calc R . .
O10 O 0.10880(10) 0.33251(12) 0.47926(5) 0.0184(2) Uani 1 1 d . . .
C11 C 0.23771(15) 0.27944(19) 0.50456(7) 0.0199(3) Uani 1 1 d . . .
H11A H 0.2339 0.2629 0.5494 0.024 Uiso 1 1 calc R . .
H11B H 0.3068 0.3603 0.4985 0.024 Uiso 1 1 calc R . .
C12 C 0.27950(16) 0.12896(18) 0.47473(7) 0.0193(3) Uani 1 1 d . . .
H12A H 0.3699 0.0968 0.4929 0.023 Uiso 1 1 calc R . .
H12B H 0.2139 0.046 0.4831 0.023 Uiso 1 1 calc R . .
N13 N 0.28427(12) 0.14827(14) 0.40822(6) 0.0160(3) Uani 1 1 d . . .
C14 C 0.38909(15) 0.20161(17) 0.37881(7) 0.0173(3) Uani 1 1 d . . .
C15 C 0.52548(16) 0.2411(2) 0.40675(8) 0.0241(4) Uani 1 1 d . . .
H15A H 0.5284 0.2242 0.4514 0.036 Uiso 0.5 1 calc PR . .
H15B H 0.5453 0.3505 0.3985 0.036 Uiso 0.5 1 calc PR . .
H15C H 0.5932 0.1749 0.389 0.036 Uiso 0.5 1 calc PR . .
H15D H 0.5829 0.2755 0.3745 0.036 Uiso 0.5 1 calc PR . .
H15E H 0.566 0.1492 0.4274 0.036 Uiso 0.5 1 calc PR . .
H15F H 0.518 0.3248 0.4369 0.036 Uiso 0.5 1 calc PR . .
N16 N 0.34839(13) 0.21073(15) 0.31909(6) 0.0204(3) Uani 1 1 d . . .
C17 C 0.43211(19) 0.2629(2) 0.27033(8) 0.0313(4) Uani 1 1 d . . .
H17A H 0.4586 0.3715 0.2776 0.047 Uiso 1 1 calc R . .
H17B H 0.3803 0.2541 0.2304 0.047 Uiso 1 1 calc R . .
H17C H 0.5136 0.1979 0.2703 0.047 Uiso 1 1 calc R . .
C18 C 0.21495(16) 0.16376(19) 0.31043(8) 0.0227(3) Uani 1 1 d . . .
H18 H 0.1614 0.1598 0.2724 0.027 Uiso 1 1 calc R . .
C19 C 0.17535(15) 0.12469(18) 0.36623(7) 0.0190(3) Uani 1 1 d . . .
H19 H 0.0883 0.0877 0.375 0.023 Uiso 1 1 calc R . .
P1 P 0.39934(4) -0.29256(5) 0.380279(19) 0.02004(12) Uani 1 1 d . . .
F51 F 0.32236(12) -0.42567(12) 0.34038(5) 0.0395(3) Uani 1 1 d . . .
F52 F 0.54156(11) -0.36425(13) 0.36358(6) 0.0426(3) Uani 1 1 d . . .
F53 F 0.39718(12) -0.18305(12) 0.32092(5) 0.0370(3) Uani 1 1 d . . .
F54 F 0.47739(13) -0.15868(13) 0.41950(6) 0.0446(3) Uani 1 1 d . . .
F55 F 0.25758(11) -0.22160(13) 0.39677(6) 0.0402(3) Uani 1 1 d . . .
F56 F 0.40227(13) -0.40124(13) 0.43969(5) 0.0397(3) Uani 1 1 d . . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.493(2) . ?
C1 H1A 0.98 . ?
C1 H1B 0.98 . ?
C1 H1C 0.98 . ?
C2 N7 1.348(2) . ?
C2 C3 1.379(2) . ?
C3 C4 1.399(2) . ?
C3 H3 0.95 . ?
C4 N6 1.3330(19) . ?
C4 C5 1.498(2) . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
N6 N7 1.3695(17) . ?
N7 C8 1.4568(19) . ?
C8 C9 1.506(2) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 O10 1.4287(18) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
O10 C11 1.4262(18) . ?
C11 C12 1.518(2) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 N13 1.4609(19) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
N13 C14 1.338(2) . ?
N13 C19 1.3759(19) . ?
C14 N16 1.335(2) . ?
C14 C15 1.478(2) . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C15 H15D 0.98 . ?
C15 H15E 0.98 . ?
C15 H15F 0.98 . ?
N16 C18 1.379(2) . ?
N16 C17 1.463(2) . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 C19 1.345(2) . ?
C18 H18 0.95 . ?
C19 H19 0.95 . ?
P1 F55 1.5931(11) . ?
P1 F56 1.5938(11) . ?
P1 F51 1.5959(11) . ?
P1 F53 1.5974(11) . ?
P1 F54 1.5979(11) . ?
P1 F52 1.6010(11) . ?


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
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 . . ?
N7 C2 C3 106.52(13) . . ?
N7 C2 C1 122.97(15) . . ?
C3 C2 C1 130.49(16) . . ?
C2 C3 C4 105.47(14) . . ?
C2 C3 H3 127.3 . . ?
C4 C3 H3 127.3 . . ?
N6 C4 C3 111.40(13) . . ?
N6 C4 C5 120.64(14) . . ?
C3 C4 C5 127.96(14) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 N6 N7 104.48(12) . . ?
C2 N7 N6 112.14(12) . . ?
C2 N7 C8 129.42(13) . . ?
N6 N7 C8 118.42(12) . . ?
N7 C8 C9 112.57(13) . . ?
N7 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N7 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
O10 C9 C8 107.96(13) . . ?
O10 C9 H9A 110.1 . . ?
C8 C9 H9A 110.1 . . ?
O10 C9 H9B 110.1 . . ?
C8 C9 H9B 110.1 . . ?
H9A C9 H9B 108.4 . . ?
C11 O10 C9 113.58(12) . . ?
O10 C11 C12 111.77(12) . . ?
O10 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
O10 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
N13 C12 C11 110.86(13) . . ?
N13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
N13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 N13 C19 109.20(13) . . ?
C14 N13 C12 126.49(13) . . ?
C19 N13 C12 124.15(13) . . ?
N16 C14 N13 107.26(13) . . ?
N16 C14 C15 126.06(14) . . ?
N13 C14 C15 126.67(15) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C15 H15D 109.5 . . ?
H15A C15 H15D 141.1 . . ?
H15B C15 H15D 56.3 . . ?
H15C C15 H15D 56.3 . . ?
C14 C15 H15E 109.5 . . ?
H15A C15 H15E 56.3 . . ?
H15B C15 H15E 141.1 . . ?
H15C C15 H15E 56.3 . . ?
H15D C15 H15E 109.5 . . ?
C14 C15 H15F 109.5 . . ?
H15A C15 H15F 56.3 . . ?
H15B C15 H15F 56.3 . . ?
H15C C15 H15F 141.1 . . ?
H15D C15 H15F 109.5 . . ?
H15E C15 H15F 109.5 . . ?
C14 N16 C18 109.49(13) . . ?
C14 N16 C17 125.30(14) . . ?
C18 N16 C17 125.21(14) . . ?
N16 C17 H17A 109.5 . . ?
N16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 N16 106.73(14) . . ?
C19 C18 H18 126.6 . . ?
N16 C18 H18 126.6 . . ?
C18 C19 N13 107.32(14) . . ?
C18 C19 H19 126.3 . . ?
N13 C19 H19 126.3 . . ?
F55 P1 F56 90.37(6) . . ?
F55 P1 F51 90.26(7) . . ?
F56 P1 F51 90.05(7) . . ?
F55 P1 F53 89.77(6) . . ?
F56 P1 F53 179.65(7) . . ?
F51 P1 F53 90.28(6) . . ?
F55 P1 F54 90.14(7) . . ?
F56 P1 F54 90.54(7) . . ?
F51 P1 F54 179.29(7) . . ?
F53 P1 F54 89.14(6) . . ?
F55 P1 F52 179.83(8) . . ?
F56 P1 F52 89.64(6) . . ?
F51 P1 F52 89.57(7) . . ?
F53 P1 F52 90.22(6) . . ?
F54 P1 F52 90.03(7) . . ?


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
N7 C2 C3 C4 -0.13(17) . . . . ?
C1 C2 C3 C4 178.24(18) . . . . ?
C2 C3 C4 N6 0.09(17) . . . . ?
C2 C3 C4 C5 -179.45(15) . . . . ?
C3 C4 N6 N7 -0.02(16) . . . . ?
C5 C4 N6 N7 179.57(13) . . . . ?
C3 C2 N7 N6 0.13(17) . . . . ?
C1 C2 N7 N6 -178.39(15) . . . . ?
C3 C2 N7 C8 -177.87(14) . . . . ?
C1 C2 N7 C8 3.6(3) . . . . ?
C4 N6 N7 C2 -0.07(16) . . . . ?
C4 N6 N7 C8 178.17(12) . . . . ?
C2 N7 C8 C9 -110.40(17) . . . . ?
N6 N7 C8 C9 71.70(17) . . . . ?
N7 C8 C9 O10 68.72(16) . . . . ?
C8 C9 O10 C11 -168.71(12) . . . . ?
C9 O10 C11 C12 84.77(15) . . . . ?
O10 C11 C12 N13 58.09(17) . . . . ?
C11 C12 N13 C14 85.80(17) . . . . ?
C11 C12 N13 C19 -88.93(17) . . . . ?
C19 N13 C14 N16 -0.50(17) . . . . ?
C12 N13 C14 N16 -175.89(13) . . . . ?
C19 N13 C14 C15 -179.68(15) . . . . ?
C12 N13 C14 C15 4.9(2) . . . . ?
N13 C14 N16 C18 0.57(17) . . . . ?
C15 C14 N16 C18 179.75(15) . . . . ?
N13 C14 N16 C17 -179.60(14) . . . . ?
C15 C14 N16 C17 -0.4(3) . . . . ?
C14 N16 C18 C19 -0.42(18) . . . . ?
C17 N16 C18 C19 179.75(15) . . . . ?
N16 C18 C19 N13 0.10(18) . . . . ?
C14 N13 C19 C18 0.24(18) . . . . ?
C12 N13 C19 C18 175.76(14) . . . . ?


####################################################################### 
# 
# 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_job
_database_code_depnum_ccdc_archive 'CCDC 1055629'
_audit_update_record             
;
2015-03-23 deposited with the CCDC.
2015-07-10 downloaded from the CCDC.
;

_audit_creation_date             2010-02-23T11:23:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C13 H21 Cl3 N4 Ni O)'
_chemical_formula_sum            'C26 H42 Cl6 N8 Ni2 O2'
_chemical_formula_weight         828.8
_chemical_compound_source        'synthesis as described'
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c 21 b'
_symmetry_space_group_name_Hall  'P -2bc -2c'
_symmetry_Int_Tables_number      29
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, y, z+1/2'
'x, y+1/2, -z+1/2'

_cell_length_a                   8.1781(2)
_cell_length_b                   15.6069(3)
_cell_length_c                   28.0616(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3581.64(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8277
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      27.42
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1712
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_correction_T_max  0.898


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_number            54557
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         3.56
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             8156
_reflns_number_gt                7804
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker SAINT (Bruker, 2002)'
_computing_cell_refinement       'Bruker SMART (Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2002)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
           WinGX publication routines (Farrugia, 1999),
           CRYSCAL (T. Roisnel, local program)
;

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0245P)²+0.1797P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         8156
_refine_ls_number_parameters     403
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0208
_refine_ls_R_factor_gt           0.0192
_refine_ls_wR_factor_ref         0.0467
_refine_ls_wR_factor_gt          0.0462
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.001
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.016(5)
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.69449(2) 0.981283(13) 0.522145(6) 0.01975(5) Uani 1 1 d . . .
Cl1 Cl 0.89220(6) 0.88172(3) 0.524899(16) 0.03858(12) Uani 1 1 d . . .
Cl2 Cl 0.78224(7) 1.11681(3) 0.516179(16) 0.04153(12) Uani 1 1 d . . .
Cl3 Cl 0.52623(5) 0.93153(3) 0.464126(15) 0.03250(10) Uani 1 1 d . . .
N1 N 0.59588(14) 0.98036(9) 0.58787(4) 0.0192(2) Uani 1 1 d . . .
N2 N 0.43534(14) 0.97689(9) 0.60141(4) 0.0184(2) Uani 1 1 d . . .
C3 C 0.86524(18) 0.98824(12) 0.62959(6) 0.0255(3) Uani 1 1 d . . .
H3A H 0.9142 0.9334 0.6204 0.038 Uiso 1 1 calc R . .
H3B H 0.9009 1.0034 0.6618 0.038 Uiso 1 1 calc R . .
H3C H 0.9001 1.0329 0.6072 0.038 Uiso 1 1 calc R . .
C4 C 0.68284(17) 0.98069(10) 0.62857(5) 0.0196(3) Uani 1 1 d . . .
C5 C 0.57797(18) 0.97586(11) 0.66756(5) 0.0229(3) Uani 1 1 d . . .
H5 H 0.6083 0.9738 0.7002 0.027 Uiso 1 1 calc R . .
C6 C 0.42115(18) 0.97472(10) 0.64936(5) 0.0205(3) Uani 1 1 d . . .
C7 C 0.26054(19) 0.97392(13) 0.67460(6) 0.0295(4) Uani 1 1 d . . .
H7A H 0.2041 1.0284 0.6691 0.044 Uiso 1 1 calc R . .
H7B H 0.2786 0.966 0.7088 0.044 Uiso 1 1 calc R . .
H7C H 0.1934 0.9268 0.6624 0.044 Uiso 1 1 calc R . .
C8 C 0.30302(18) 0.97658(12) 0.56631(5) 0.0230(3) Uani 1 1 d . . .
H8A H 0.1993 0.9618 0.5826 0.028 Uiso 1 1 calc R . .
H8B H 0.3252 0.9315 0.5423 0.028 Uiso 1 1 calc R . .
C9 C 0.2823(2) 1.06134(11) 0.54103(6) 0.0252(3) Uani 1 1 d . . .
H9A H 0.3852 1.0768 0.5245 0.03 Uiso 1 1 calc R . .
H9B H 0.1947 1.0566 0.5168 0.03 Uiso 1 1 calc R . .
O10 O 0.24121(14) 1.12627(7) 0.57472(4) 0.0249(2) Uani 1 1 d . . .
C11 C 0.2376(2) 1.20805(11) 0.55188(6) 0.0289(4) Uani 1 1 d . . .
H11A H 0.1601 1.2068 0.5248 0.035 Uiso 1 1 calc R . .
H11B H 0.3475 1.2223 0.5394 0.035 Uiso 1 1 calc R . .
C12 C 0.1849(2) 1.27464(12) 0.58758(6) 0.0311(4) Uani 1 1 d . . .
H12A H 0.2472 1.2664 0.6175 0.037 Uiso 1 1 calc R . .
H12B H 0.2116 1.3322 0.575 0.037 Uiso 1 1 calc R . .
N13 N 0.00878(17) 1.27058(9) 0.59818(5) 0.0257(3) Uani 1 1 d . . .
C14 C -0.0611(2) 1.22414(11) 0.63182(6) 0.0286(4) Uani 1 1 d . . .
H14 H -0.0061 1.1888 0.6542 0.034 Uiso 1 1 calc R . .
N15 N -0.22335(19) 1.23554(8) 0.62885(5) 0.0278(3) Uani 1 1 d . . .
C16 C -0.3458(3) 1.19592(13) 0.65986(8) 0.0442(5) Uani 1 1 d . . .
H16A H -0.291 1.1595 0.6834 0.066 Uiso 1 1 calc R . .
H16B H -0.4203 1.161 0.6406 0.066 Uiso 1 1 calc R . .
H16C H -0.4079 1.2407 0.6763 0.066 Uiso 1 1 calc R . .
C17 C -0.2558(2) 1.29092(11) 0.59239(6) 0.0314(4) Uani 1 1 d . . .
H17 H -0.3606 1.3104 0.5827 0.038 Uiso 1 1 calc R . .
C18 C -0.1116(2) 1.31269(11) 0.57287(6) 0.0304(4) Uani 1 1 d . . .
H18 H -0.0955 1.3501 0.5466 0.036 Uiso 1 1 calc R . .
Ni2 Ni 0.09927(2) 0.763901(13) 0.742351(7) 0.02262(5) Uani 1 1 d . . .
Cl21 Cl -0.12578(5) 0.84736(3) 0.749865(17) 0.03636(11) Uani 1 1 d . . .
Cl22 Cl 0.02088(6) 0.62661(3) 0.753860(15) 0.03359(10) Uani 1 1 d . . .
Cl23 Cl 0.28542(5) 0.82925(3) 0.790347(14) 0.03339(10) Uani 1 1 d . . .
N21 N 0.17654(14) 0.75632(9) 0.67417(5) 0.0193(3) Uani 1 1 d . . .
N22 N 0.33367(14) 0.75667(8) 0.65634(5) 0.0191(3) Uani 1 1 d . . .
C23 C -0.10379(18) 0.74649(11) 0.63985(6) 0.0254(4) Uani 1 1 d . . .
H23A H -0.1349 0.6935 0.6563 0.038 Uiso 1 1 calc R . .
H23B H -0.1527 0.7472 0.608 0.038 Uiso 1 1 calc R . .
H23C H -0.1431 0.7959 0.6581 0.038 Uiso 1 1 calc R . .
C24 C 0.07913(18) 0.75080(10) 0.63559(6) 0.0204(3) Uani 1 1 d . . .
C25 C 0.17211(19) 0.74808(10) 0.59416(6) 0.0226(3) Uani 1 1 d . . .
H25 H 0.1324 0.7447 0.5624 0.027 Uiso 1 1 calc R . .
C26 C 0.33323(19) 0.75130(10) 0.60829(6) 0.0210(3) Uani 1 1 d . . .
C27 C 0.4858(2) 0.74782(12) 0.57902(6) 0.0303(4) Uani 1 1 d . . .
H27A H 0.549 0.8005 0.5839 0.046 Uiso 1 1 calc R . .
H27B H 0.457 0.7424 0.5453 0.046 Uiso 1 1 calc R . .
H27C H 0.5515 0.6983 0.5887 0.046 Uiso 1 1 calc R . .
C28 C 0.47616(17) 0.75960(11) 0.68782(6) 0.0229(3) Uani 1 1 d . . .
H28A H 0.4579 0.8041 0.7124 0.027 Uiso 1 1 calc R . .
H28B H 0.573 0.7768 0.6689 0.027 Uiso 1 1 calc R . .
C29 C 0.5124(2) 0.67552(10) 0.71230(6) 0.0238(3) Uani 1 1 d . . .
H29A H 0.6045 0.683 0.7348 0.029 Uiso 1 1 calc R . .
H29B H 0.4154 0.6568 0.7307 0.029 Uiso 1 1 calc R . .
O30 O 0.55347(12) 0.61187(7) 0.67763(4) 0.0204(2) Uani 1 1 d . . .
C31 C 0.59221(18) 0.53283(10) 0.69985(6) 0.0216(3) Uani 1 1 d . . .
H31A H 0.4958 0.5111 0.7174 0.026 Uiso 1 1 calc R . .
H31B H 0.6824 0.5412 0.7229 0.026 Uiso 1 1 calc R . .
C32 C 0.64269(18) 0.46889(10) 0.66258(6) 0.0222(3) Uani 1 1 d . . .
H32A H 0.6583 0.4122 0.6777 0.027 Uiso 1 1 calc R . .
H32B H 0.5545 0.4634 0.6386 0.027 Uiso 1 1 calc R . .
N33 N 0.79490(14) 0.49453(8) 0.63868(4) 0.0178(3) Uani 1 1 d . . .
C34 C 0.94424(18) 0.48998(10) 0.65758(6) 0.0204(3) Uani 1 1 d . . .
H34 H 0.9703 0.4685 0.6883 0.025 Uiso 1 1 calc R . .
N35 N 1.05034(15) 0.52057(8) 0.62602(5) 0.0215(3) Uani 1 1 d . . .
C36 C 1.22700(19) 0.52913(12) 0.63481(7) 0.0308(4) Uani 1 1 d . . .
H36A H 1.2484 0.5832 0.6514 0.046 Uiso 1 1 calc R . .
H36B H 1.2856 0.5287 0.6043 0.046 Uiso 1 1 calc R . .
H36C H 1.2646 0.4812 0.6545 0.046 Uiso 1 1 calc R . .
C37 C 0.9676(2) 0.54593(11) 0.58578(6) 0.0248(3) Uani 1 1 d . . .
H37 H 1.014 0.5702 0.5578 0.03 Uiso 1 1 calc R . .
C38 C 0.80735(18) 0.52961(10) 0.59360(6) 0.0234(3) Uani 1 1 d . . .
H38 H 0.7198 0.5403 0.5721 0.028 Uiso 1 1 calc R . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N1 2.0131(12) . ?
Ni1 Cl2 2.2398(5) . ?
Ni1 Cl1 2.2439(5) . ?
Ni1 Cl3 2.2687(4) . ?
N1 C4 1.3453(19) . ?
N1 N2 1.3678(16) . ?
N2 C6 1.3512(19) . ?
N2 C8 1.4633(18) . ?
C3 C4 1.497(2) . ?
C3 H3A 0.98 . ?
C3 H3B 0.98 . ?
C3 H3C 0.98 . ?
C4 C5 1.392(2) . ?
C5 C6 1.380(2) . ?
C5 H5 0.95 . ?
C6 C7 1.492(2) . ?
C7 H7A 0.98 . ?
C7 H7B 0.98 . ?
C7 H7C 0.98 . ?
C8 C9 1.511(2) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 O10 1.4262(19) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
O10 C11 1.428(2) . ?
C11 C12 1.506(2) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 N13 1.472(2) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
N13 C14 1.320(2) . ?
N13 C18 1.380(2) . ?
C14 N15 1.341(2) . ?
C14 H14 0.95 . ?
N15 C17 1.365(2) . ?
N15 C16 1.464(2) . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 C18 1.344(3) . ?
C17 H17 0.95 . ?
C18 H18 0.95 . ?
Ni2 N21 2.0184(13) . ?
Ni2 Cl22 2.2597(5) . ?
Ni2 Cl21 2.2646(5) . ?
Ni2 Cl23 2.2741(5) . ?
N21 C24 1.3467(19) . ?
N21 N22 1.3789(16) . ?
N22 C26 1.351(2) . ?
N22 C28 1.4630(19) . ?
C23 C24 1.502(2) . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?
C24 C25 1.390(2) . ?
C25 C26 1.377(2) . ?
C25 H25 0.95 . ?
C26 C27 1.495(2) . ?
C27 H27A 0.98 . ?
C27 H27B 0.98 . ?
C27 H27C 0.98 . ?
C28 C29 1.510(2) . ?
C28 H28A 0.99 . ?
C28 H28B 0.99 . ?
C29 O30 1.4305(18) . ?
C29 H29A 0.99 . ?
C29 H29B 0.99 . ?
O30 C31 1.4181(19) . ?
C31 C32 1.503(2) . ?
C31 H31A 0.99 . ?
C31 H31B 0.99 . ?
C32 N33 1.4696(19) . ?
C32 H32A 0.99 . ?
C32 H32B 0.99 . ?
N33 C34 1.3333(19) . ?
N33 C38 1.382(2) . ?
C34 N35 1.328(2) . ?
C34 H34 0.95 . ?
N35 C37 1.375(2) . ?
N35 C36 1.4717(19) . ?
C36 H36A 0.98 . ?
C36 H36B 0.98 . ?
C36 H36C 0.98 . ?
C37 C38 1.353(2) . ?
C37 H37 0.95 . ?
C38 H38 0.95 . ?


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 Cl2 101.75(4) . . ?
N1 Ni1 Cl1 104.61(4) . . ?
Cl2 Ni1 Cl1 115.19(2) . . ?
N1 Ni1 Cl3 114.34(4) . . ?
Cl2 Ni1 Cl3 117.64(2) . . ?
Cl1 Ni1 Cl3 102.988(18) . . ?
C4 N1 N2 105.78(11) . . ?
C4 N1 Ni1 124.47(9) . . ?
N2 N1 Ni1 129.73(9) . . ?
C6 N2 N1 111.10(12) . . ?
C6 N2 C8 127.36(12) . . ?
N1 N2 C8 121.54(12) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C5 109.95(12) . . ?
N1 C4 C3 122.91(13) . . ?
C5 C4 C3 127.11(13) . . ?
C6 C5 C4 106.40(13) . . ?
C6 C5 H5 126.8 . . ?
C4 C5 H5 126.8 . . ?
N2 C6 C5 106.75(13) . . ?
N2 C6 C7 123.26(14) . . ?
C5 C6 C7 129.96(15) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C9 113.33(14) . . ?
N2 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
N2 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
O10 C9 C8 109.72(13) . . ?
O10 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
O10 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C9 O10 C11 110.03(12) . . ?
O10 C11 C12 108.90(14) . . ?
O10 C11 H11A 109.9 . . ?
C12 C11 H11A 109.9 . . ?
O10 C11 H11B 109.9 . . ?
C12 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
N13 C12 C11 112.61(14) . . ?
N13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
N13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C14 N13 C18 108.68(15) . . ?
C14 N13 C12 126.27(15) . . ?
C18 N13 C12 125.00(14) . . ?
N13 C14 N15 108.12(15) . . ?
N13 C14 H14 125.9 . . ?
N15 C14 H14 125.9 . . ?
C14 N15 C17 108.83(15) . . ?
C14 N15 C16 125.70(16) . . ?
C17 N15 C16 125.46(17) . . ?
N15 C16 H16A 109.5 . . ?
N15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 N15 107.17(16) . . ?
C18 C17 H17 126.4 . . ?
N15 C17 H17 126.4 . . ?
C17 C18 N13 107.20(15) . . ?
C17 C18 H18 126.4 . . ?
N13 C18 H18 126.4 . . ?
N21 Ni2 Cl22 99.71(4) . . ?
N21 Ni2 Cl21 112.11(4) . . ?
Cl22 Ni2 Cl21 107.55(2) . . ?
N21 Ni2 Cl23 112.22(4) . . ?
Cl22 Ni2 Cl23 122.041(19) . . ?
Cl21 Ni2 Cl23 103.354(18) . . ?
C24 N21 N22 105.06(12) . . ?
C24 N21 Ni2 125.49(10) . . ?
N22 N21 Ni2 129.44(10) . . ?
C26 N22 N21 111.06(12) . . ?
C26 N22 C28 127.35(13) . . ?
N21 N22 C28 121.56(12) . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N21 C24 C25 110.53(13) . . ?
N21 C24 C23 121.87(14) . . ?
C25 C24 C23 127.59(14) . . ?
C26 C25 C24 106.35(14) . . ?
C26 C25 H25 126.8 . . ?
C24 C25 H25 126.8 . . ?
N22 C26 C25 106.99(13) . . ?
N22 C26 C27 123.26(14) . . ?
C25 C26 C27 129.74(15) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N22 C28 C29 113.79(13) . . ?
N22 C28 H28A 108.8 . . ?
C29 C28 H28A 108.8 . . ?
N22 C28 H28B 108.8 . . ?
C29 C28 H28B 108.8 . . ?
H28A C28 H28B 107.7 . . ?
O30 C29 C28 109.88(12) . . ?
O30 C29 H29A 109.7 . . ?
C28 C29 H29A 109.7 . . ?
O30 C29 H29B 109.7 . . ?
C28 C29 H29B 109.7 . . ?
H29A C29 H29B 108.2 . . ?
C31 O30 C29 110.95(11) . . ?
O30 C31 C32 109.44(13) . . ?
O30 C31 H31A 109.8 . . ?
C32 C31 H31A 109.8 . . ?
O30 C31 H31B 109.8 . . ?
C32 C31 H31B 109.8 . . ?
H31A C31 H31B 108.2 . . ?
N33 C32 C31 111.68(13) . . ?
N33 C32 H32A 109.3 . . ?
C31 C32 H32A 109.3 . . ?
N33 C32 H32B 109.3 . . ?
C31 C32 H32B 109.3 . . ?
H32A C32 H32B 107.9 . . ?
C34 N33 C38 108.52(12) . . ?
C34 N33 C32 125.43(13) . . ?
C38 N33 C32 126.02(13) . . ?
N35 C34 N33 108.30(13) . . ?
N35 C34 H34 125.8 . . ?
N33 C34 H34 125.8 . . ?
C34 N35 C37 109.23(13) . . ?
C34 N35 C36 124.21(14) . . ?
C37 N35 C36 126.50(14) . . ?
N35 C36 H36A 109.5 . . ?
N35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
N35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C38 C37 N35 106.82(14) . . ?
C38 C37 H37 126.6 . . ?
N35 C37 H37 126.6 . . ?
C37 C38 N33 107.13(13) . . ?
C37 C38 H38 126.4 . . ?
N33 C38 H38 126.4 . . ?


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
Cl2 Ni1 N1 C4 -73.84(13) . . . . ?
Cl1 Ni1 N1 C4 46.39(14) . . . . ?
Cl3 Ni1 N1 C4 158.28(12) . . . . ?
Cl2 Ni1 N1 N2 108.23(13) . . . . ?
Cl1 Ni1 N1 N2 -131.54(13) . . . . ?
Cl3 Ni1 N1 N2 -19.65(15) . . . . ?
C4 N1 N2 C6 -0.25(18) . . . . ?
Ni1 N1 N2 C6 177.98(11) . . . . ?
C4 N1 N2 C8 179.25(14) . . . . ?
Ni1 N1 N2 C8 -2.5(2) . . . . ?
N2 N1 C4 C5 1.08(18) . . . . ?
Ni1 N1 C4 C5 -177.26(11) . . . . ?
N2 N1 C4 C3 -177.06(15) . . . . ?
Ni1 N1 C4 C3 4.6(2) . . . . ?
N1 C4 C5 C6 -1.5(2) . . . . ?
C3 C4 C5 C6 176.54(16) . . . . ?
N1 N2 C6 C5 -0.68(18) . . . . ?
C8 N2 C6 C5 179.86(16) . . . . ?
N1 N2 C6 C7 177.75(15) . . . . ?
C8 N2 C6 C7 -1.7(3) . . . . ?
C4 C5 C6 N2 1.30(19) . . . . ?
C4 C5 C6 C7 -176.99(17) . . . . ?
C6 N2 C8 C9 109.18(18) . . . . ?
N1 N2 C8 C9 -70.23(19) . . . . ?
N2 C8 C9 O10 -61.85(17) . . . . ?
C8 C9 O10 C11 174.20(13) . . . . ?
C9 O10 C11 C12 176.92(14) . . . . ?
O10 C11 C12 N13 -74.50(18) . . . . ?
C11 C12 N13 C14 89.5(2) . . . . ?
C11 C12 N13 C18 -87.72(19) . . . . ?
C18 N13 C14 N15 -0.17(18) . . . . ?
C12 N13 C14 N15 -177.74(14) . . . . ?
N13 C14 N15 C17 -0.20(19) . . . . ?
N13 C14 N15 C16 -179.60(16) . . . . ?
C14 N15 C17 C18 0.49(19) . . . . ?
C16 N15 C17 C18 179.90(17) . . . . ?
N15 C17 C18 N13 -0.58(19) . . . . ?
C14 N13 C18 C17 0.47(19) . . . . ?
C12 N13 C18 C17 178.09(15) . . . . ?
Cl22 Ni2 N21 C24 74.72(13) . . . . ?
Cl21 Ni2 N21 C24 -38.84(14) . . . . ?
Cl23 Ni2 N21 C24 -154.64(12) . . . . ?
Cl22 Ni2 N21 N22 -106.24(13) . . . . ?
Cl21 Ni2 N21 N22 140.20(12) . . . . ?
Cl23 Ni2 N21 N22 24.40(14) . . . . ?
C24 N21 N22 C26 -0.16(17) . . . . ?
Ni2 N21 N22 C26 -179.35(11) . . . . ?
C24 N21 N22 C28 -178.23(14) . . . . ?
Ni2 N21 N22 C28 2.6(2) . . . . ?
N22 N21 C24 C25 -0.25(17) . . . . ?
Ni2 N21 C24 C25 178.98(11) . . . . ?
N22 N21 C24 C23 178.51(13) . . . . ?
Ni2 N21 C24 C23 -2.3(2) . . . . ?
N21 C24 C25 C26 0.56(18) . . . . ?
C23 C24 C25 C26 -178.11(15) . . . . ?
N21 N22 C26 C25 0.51(17) . . . . ?
C28 N22 C26 C25 178.44(15) . . . . ?
N21 N22 C26 C27 -178.22(15) . . . . ?
C28 N22 C26 C27 -0.3(3) . . . . ?
C24 C25 C26 N22 -0.64(17) . . . . ?
C24 C25 C26 C27 177.99(17) . . . . ?
C26 N22 C28 C29 -102.37(18) . . . . ?
N21 N22 C28 C29 75.36(18) . . . . ?
N22 C28 C29 O30 63.62(17) . . . . ?
C28 C29 O30 C31 178.46(12) . . . . ?
C29 O30 C31 C32 -177.23(12) . . . . ?
O30 C31 C32 N33 64.93(16) . . . . ?
C31 C32 N33 C34 74.36(19) . . . . ?
C31 C32 N33 C38 -103.60(17) . . . . ?
C38 N33 C34 N35 -0.23(17) . . . . ?
C32 N33 C34 N35 -178.50(13) . . . . ?
N33 C34 N35 C37 0.27(18) . . . . ?
N33 C34 N35 C36 177.49(14) . . . . ?
C34 N35 C37 C38 -0.21(18) . . . . ?
C36 N35 C37 C38 -177.34(15) . . . . ?
N35 C37 C38 N33 0.06(18) . . . . ?
C34 N33 C38 C37 0.10(18) . . . . ?
C32 N33 C38 C37 178.36(14) . . . . ?


####################################################################### 
# 
# 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_job
_database_code_depnum_ccdc_archive 'CCDC 1055632'
_audit_update_record             
;
2015-03-23 deposited with the CCDC.
2015-07-10 downloaded from the CCDC.
;

_audit_creation_date             2010-06-23T12:33:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H19 Cl3 N4 Ni O'
_chemical_formula_sum            'C12 H19 Cl3 N4 Ni O'
_chemical_formula_weight         400.37
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.3830(6)
_cell_length_b                   7.7341(3)
_cell_length_c                   17.1341(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.377(2)
_cell_angle_gamma                90
_cell_volume                     1717.93(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4696
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      27.31
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_T_max  0.909


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.035
_diffrn_reflns_number            13838
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             3899
_reflns_number_gt                3240
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker SAINT (Bruker, 2002)'
_computing_cell_refinement       'Bruker SMART (Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2002)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999))'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
           WinGX publication routines (Farrugia, 1999),
           CRYSCAL (T. Roisnel, local program)
;

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0337P)²+0.5423P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3899
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0748
_refine_ls_wR_factor_gt          0.0703
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.064

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.261069(19) 0.29117(3) 0.864367(15) 0.02349(9) Uani 1 1 d . . .
Cl1 Cl 0.29651(4) 0.38826(8) 0.75043(3) 0.03459(14) Uani 1 1 d . . .
Cl2 Cl 0.21506(4) 0.00896(6) 0.84779(3) 0.02848(12) Uani 1 1 d . . .
Cl3 Cl 0.14649(4) 0.43240(7) 0.91998(3) 0.03172(13) Uani 1 1 d . . .
N1 N 0.39210(12) 0.2856(2) 0.95177(10) 0.0227(3) Uani 1 1 d . . .
C2 C 0.40713(17) 0.3498(3) 1.02635(12) 0.0278(4) Uani 1 1 d . . .
H2 H 0.3564 0.4096 1.046 0.033 Uiso 1 1 calc R . .
C3 C 0.50717(17) 0.3170(3) 1.07117(13) 0.0323(5) Uani 1 1 d . . .
H3 H 0.5372 0.3491 1.1255 0.039 Uiso 1 1 calc R . .
C4 C 0.55324(16) 0.2282(3) 1.01994(13) 0.0304(5) Uani 1 1 d . . .
H4 H 0.6222 0.1867 1.0325 0.036 Uiso 1 1 calc R . .
N5 N 0.48303(12) 0.2106(2) 0.94855(10) 0.0236(4) Uani 1 1 d . . .
C6 C 0.49924(16) 0.1319(3) 0.87501(13) 0.0276(4) Uani 1 1 d . . .
H6A H 0.4321 0.0909 0.8416 0.033 Uiso 1 1 calc R . .
H6B H 0.5446 0.0298 0.8898 0.033 Uiso 1 1 calc R . .
C7 C 0.54690(15) 0.2536(3) 0.82534(13) 0.0284(5) Uani 1 1 d . . .
H7A H 0.5505 0.1973 0.7742 0.034 Uiso 1 1 calc R . .
H7B H 0.5044 0.3595 0.8123 0.034 Uiso 1 1 calc R . .
O8 O 0.64779(10) 0.29675(18) 0.87110(8) 0.0257(3) Uani 1 1 d . . .
C9 C 0.70869(15) 0.3747(3) 0.82322(12) 0.0269(4) Uani 1 1 d . . .
H9A H 0.6833 0.4929 0.807 0.032 Uiso 1 1 calc R . .
H9B H 0.7048 0.3056 0.7739 0.032 Uiso 1 1 calc R . .
C10 C 0.81877(15) 0.3816(3) 0.87396(13) 0.0262(4) Uani 1 1 d . . .
H10A H 0.8636 0.4337 0.8422 0.031 Uiso 1 1 calc R . .
H10B H 0.8223 0.4552 0.9218 0.031 Uiso 1 1 calc R . .
N11 N 0.85585(12) 0.2068(2) 0.89990(9) 0.0210(3) Uani 1 1 d . . .
C12 C 0.83557(15) 0.1213(3) 0.96514(12) 0.0275(4) Uani 1 1 d . . .
H12 H 0.802 0.1681 1.0031 0.033 Uiso 1 1 calc R . .
C13 C 0.87227(15) -0.0406(3) 0.96480(12) 0.0278(5) Uani 1 1 d . . .
H13 H 0.8692 -0.1296 1.0023 0.033 Uiso 1 1 calc R . .
N14 N 0.91552(12) -0.0528(2) 0.89925(10) 0.0234(4) Uani 1 1 d . . .
C15 C 0.96175(17) -0.2082(3) 0.87432(14) 0.0313(5) Uani 1 1 d . . .
H15A H 0.916 -0.2546 0.825 0.047 Uiso 1 1 calc R . .
H15B H 0.9716 -0.2951 0.9172 0.047 Uiso 1 1 calc R . .
H15C H 1.0286 -0.1789 0.8641 0.047 Uiso 1 1 calc R . .
C16 C 0.90388(14) 0.0986(3) 0.85965(11) 0.0207(4) Uani 1 1 d . . .
C17 C 0.93770(15) 0.1392(3) 0.78593(12) 0.0257(4) Uani 1 1 d . . .
H17A H 1.004 0.1999 0.8006 0.038 Uiso 1 1 calc R . .
H17B H 0.8861 0.213 0.7506 0.038 Uiso 1 1 calc R . .
H17C H 0.9454 0.0318 0.7577 0.038 Uiso 1 1 calc R . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N1 2.0039(16) . ?
Ni1 Cl1 2.2493(6) . ?
Ni1 Cl2 2.2665(6) . ?
Ni1 Cl3 2.2755(6) . ?
N1 C2 1.339(3) . ?
N1 N5 1.361(2) . ?
C2 C3 1.391(3) . ?
C2 H2 0.95 . ?
C3 C4 1.375(3) . ?
C3 H3 0.95 . ?
C4 N5 1.352(3) . ?
C4 H4 0.95 . ?
N5 C6 1.463(3) . ?
C6 C7 1.512(3) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 O8 1.422(2) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
O8 C9 1.426(2) . ?
C9 C10 1.514(3) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 N11 1.470(3) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
N11 C16 1.345(2) . ?
N11 C12 1.383(3) . ?
C12 C13 1.345(3) . ?
C12 H12 0.95 . ?
C13 N14 1.389(3) . ?
C13 H13 0.95 . ?
N14 C16 1.342(3) . ?
N14 C15 1.463(3) . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 C17 1.478(3) . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?


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 Cl1 108.77(5) . . ?
N1 Ni1 Cl2 103.47(5) . . ?
Cl1 Ni1 Cl2 108.78(2) . . ?
N1 Ni1 Cl3 104.66(5) . . ?
Cl1 Ni1 Cl3 120.82(2) . . ?
Cl2 Ni1 Cl3 108.93(2) . . ?
C2 N1 N5 105.83(16) . . ?
C2 N1 Ni1 126.97(14) . . ?
N5 N1 Ni1 127.16(13) . . ?
N1 C2 C3 110.80(19) . . ?
N1 C2 H2 124.6 . . ?
C3 C2 H2 124.6 . . ?
C4 C3 C2 105.14(19) . . ?
C4 C3 H3 127.4 . . ?
C2 C3 H3 127.4 . . ?
N5 C4 C3 107.88(19) . . ?
N5 C4 H4 126.1 . . ?
C3 C4 H4 126.1 . . ?
C4 N5 N1 110.36(17) . . ?
C4 N5 C6 127.07(18) . . ?
N1 N5 C6 122.50(16) . . ?
N5 C6 C7 113.50(17) . . ?
N5 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
N5 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
O8 C7 C6 108.13(16) . . ?
O8 C7 H7A 110.1 . . ?
C6 C7 H7A 110.1 . . ?
O8 C7 H7B 110.1 . . ?
C6 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
C7 O8 C9 112.46(15) . . ?
O8 C9 C10 107.34(16) . . ?
O8 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
O8 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
N11 C10 C9 110.42(16) . . ?
N11 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
N11 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C16 N11 C12 109.34(17) . . ?
C16 N11 C10 125.86(16) . . ?
C12 N11 C10 124.41(17) . . ?
C13 C12 N11 107.25(18) . . ?
C13 C12 H12 126.4 . . ?
N11 C12 H12 126.4 . . ?
C12 C13 N14 107.03(18) . . ?
C12 C13 H13 126.5 . . ?
N14 C13 H13 126.5 . . ?
C16 N14 C13 109.27(17) . . ?
C16 N14 C15 124.97(17) . . ?
C13 N14 C15 125.69(18) . . ?
N14 C15 H15A 109.5 . . ?
N14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N14 C16 N11 107.10(17) . . ?
N14 C16 C17 126.58(18) . . ?
N11 C16 C17 126.32(18) . . ?
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 . . ?


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
Cl1 Ni1 N1 C2 131.07(16) . . . . ?
Cl2 Ni1 N1 C2 -113.39(16) . . . . ?
Cl3 Ni1 N1 C2 0.65(18) . . . . ?
Cl1 Ni1 N1 N5 -51.42(16) . . . . ?
Cl2 Ni1 N1 N5 64.12(15) . . . . ?
Cl3 Ni1 N1 N5 178.17(14) . . . . ?
N5 N1 C2 C3 0.1(2) . . . . ?
Ni1 N1 C2 C3 178.07(14) . . . . ?
N1 C2 C3 C4 -0.1(2) . . . . ?
C2 C3 C4 N5 0.1(2) . . . . ?
C3 C4 N5 N1 0.0(2) . . . . ?
C3 C4 N5 C6 176.94(19) . . . . ?
C2 N1 N5 C4 -0.1(2) . . . . ?
Ni1 N1 N5 C4 -178.00(14) . . . . ?
C2 N1 N5 C6 -177.19(17) . . . . ?
Ni1 N1 N5 C6 4.9(3) . . . . ?
C4 N5 C6 C7 -83.0(2) . . . . ?
N1 N5 C6 C7 93.7(2) . . . . ?
N5 C6 C7 O8 64.7(2) . . . . ?
C6 C7 O8 C9 165.27(16) . . . . ?
C7 O8 C9 C10 -168.95(16) . . . . ?
O8 C9 C10 N11 58.4(2) . . . . ?
C9 C10 N11 C16 90.0(2) . . . . ?
C9 C10 N11 C12 -82.0(2) . . . . ?
C16 N11 C12 C13 0.4(2) . . . . ?
C10 N11 C12 C13 173.49(17) . . . . ?
N11 C12 C13 N14 0.3(2) . . . . ?
C12 C13 N14 C16 -0.9(2) . . . . ?
C12 C13 N14 C15 -177.94(18) . . . . ?
C13 N14 C16 N11 1.1(2) . . . . ?
C15 N14 C16 N11 178.18(16) . . . . ?
C13 N14 C16 C17 -179.08(18) . . . . ?
C15 N14 C16 C17 -2.0(3) . . . . ?
C12 N11 C16 N14 -0.9(2) . . . . ?
C10 N11 C16 N14 -173.93(16) . . . . ?
C12 N11 C16 C17 179.28(18) . . . . ?
C10 N11 C16 C17 6.3(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_job
_database_code_depnum_ccdc_archive 'CCDC 1406895'
_audit_update_record             
;
2015-06-15 deposited with the CCDC.
2015-07-10 downloaded from the CCDC.
;

_audit_creation_date             2010-04-07T18:02:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H23 Cl3 N4 Ni O'
_chemical_formula_sum            'C14 H23 Cl3 N4 Ni O'
_chemical_formula_weight         428.42
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.08500(10)
_cell_length_b                   17.5163(3)
_cell_length_c                   13.4475(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.5100(10)
_cell_angle_gamma                90
_cell_volume                     1878.25(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8690
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.49
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_T_max  0.876


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_number            15723
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_reflns_number_total             4278
_reflns_number_gt                3887
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker SAINT (Bruker, 2002)'
_computing_cell_refinement       'Bruker SMART (Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2002)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999))'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
           WinGX publication routines (Farrugia, 1999),
           CRYSCAL (T. Roisnel, local program)
;

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0270P)²+1.4470P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4278
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0638
_refine_ls_wR_factor_gt          0.061
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.777
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.058

# End of res file
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.46070(2) 0.199037(11) 0.282697(15) 0.01531(7) Uani 1 1 d . . .
Cl1 Cl 0.29367(5) 0.27436(2) 0.17483(3) 0.02269(10) Uani 1 1 d . . .
Cl2 Cl 0.35150(6) 0.17661(2) 0.42364(3) 0.02466(10) Uani 1 1 d . . .
Cl3 Cl 0.52952(5) 0.07873(2) 0.24224(3) 0.02367(10) Uani 1 1 d . . .
N4 N 0.66993(16) 0.26316(7) 0.31030(10) 0.0146(3) Uani 1 1 d . . .
N5 N 0.71466(16) 0.31542(7) 0.38557(10) 0.0143(3) Uani 1 1 d . . .
C6 C 0.7876(2) 0.21782(10) 0.16110(14) 0.0257(4) Uani 1 1 d . . .
H6A H 0.7751 0.1639 0.1776 0.039 Uiso 1 1 calc R . .
H6B H 0.8919 0.2249 0.1341 0.039 Uiso 1 1 calc R . .
H6C H 0.6923 0.2338 0.1106 0.039 Uiso 1 1 calc R . .
C7 C 0.7928(2) 0.26494(9) 0.25410(12) 0.0175(3) Uani 1 1 d . . .
C8 C 0.9157(2) 0.31726(10) 0.29413(13) 0.0206(3) Uani 1 1 d . . .
H8 H 1.0162 0.3288 0.2692 0.025 Uiso 1 1 calc R . .
C9 C 0.8627(2) 0.34889(9) 0.37694(13) 0.0187(3) Uani 1 1 d . . .
C10 C 0.9400(2) 0.40996(11) 0.44717(14) 0.0283(4) Uani 1 1 d . . .
H10A H 0.865 0.4543 0.442 0.042 Uiso 1 1 calc R . .
H10B H 1.0479 0.4251 0.4291 0.042 Uiso 1 1 calc R . .
H10C H 0.9576 0.3906 0.5165 0.042 Uiso 1 1 calc R . .
C11 C 0.6111(2) 0.33086(9) 0.46240(12) 0.0169(3) Uani 1 1 d . . .
H11A H 0.678 0.36 0.5181 0.02 Uiso 1 1 calc R . .
H11B H 0.5789 0.2818 0.4903 0.02 Uiso 1 1 calc R . .
C12 C 0.4542(2) 0.37536(9) 0.42248(12) 0.0181(3) Uani 1 1 d . . .
H12A H 0.38 0.3445 0.3719 0.022 Uiso 1 1 calc R . .
H12B H 0.3926 0.3876 0.4782 0.022 Uiso 1 1 calc R . .
O13 O 0.50061(14) 0.44373(6) 0.37754(9) 0.0196(2) Uani 1 1 d . . .
C14 C 0.3592(2) 0.48571(10) 0.33017(13) 0.0214(3) Uani 1 1 d . . .
H14A H 0.318 0.5196 0.3797 0.026 Uiso 1 1 calc R . .
H14B H 0.2676 0.4504 0.3022 0.026 Uiso 1 1 calc R . .
C15 C 0.4124(2) 0.53277(9) 0.24629(13) 0.0201(3) Uani 1 1 d . . .
H15A H 0.318 0.5655 0.2154 0.024 Uiso 1 1 calc R . .
H15B H 0.5071 0.5663 0.2745 0.024 Uiso 1 1 calc R . .
N16 N 0.46327(18) 0.48328(8) 0.16924(11) 0.0200(3) Uani 1 1 d . . .
C17 C 0.6268(2) 0.45793(10) 0.17035(13) 0.0224(4) Uani 1 1 d . . .
H17 H 0.7223 0.4711 0.2184 0.027 Uiso 1 1 calc R . .
C18 C 0.6241(2) 0.41182(10) 0.09161(14) 0.0226(4) Uani 1 1 d . . .
H18 H 0.7176 0.3859 0.073 0.027 Uiso 1 1 calc R . .
N19 N 0.45926(19) 0.40840(8) 0.04148(11) 0.0210(3) Uani 1 1 d . . .
C20 C 0.4012(2) 0.35884(10) -0.04501(13) 0.0228(4) Uani 1 1 d . . .
H20A H 0.3491 0.313 -0.022 0.034 Uiso 1 1 calc R . .
H20B H 0.4967 0.3441 -0.0771 0.034 Uiso 1 1 calc R . .
H20C H 0.3188 0.3863 -0.0938 0.034 Uiso 1 1 calc R . .
C21 C 0.3640(2) 0.45120(9) 0.09099(13) 0.0203(3) Uani 1 1 d . . .
C22 C 0.1806(2) 0.45988(11) 0.06440(15) 0.0280(4) Uani 1 1 d . . .
H22A H 0.1487 0.4613 -0.0091 0.042 Uiso 1 1 calc R . .
H22B H 0.1459 0.5075 0.0933 0.042 Uiso 1 1 calc R . .
H22C H 0.1252 0.4166 0.0913 0.042 Uiso 1 1 calc R . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N4 2.0133(13) . ?
Ni1 Cl1 2.2408(4) . ?
Ni1 Cl2 2.2537(5) . ?
Ni1 Cl3 2.2685(4) . ?
N4 C7 1.344(2) . ?
N4 N5 1.3684(18) . ?
N5 C9 1.355(2) . ?
N5 C11 1.459(2) . ?
C6 C7 1.493(2) . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C7 C8 1.393(2) . ?
C8 C9 1.374(2) . ?
C8 H8 0.95 . ?
C9 C10 1.494(2) . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 C12 1.509(2) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C12 O13 1.4194(19) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
O13 C14 1.419(2) . ?
C14 C15 1.516(2) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 N16 1.461(2) . ?
C15 H15A 0.99 . ?
C15 H15B 0.99 . ?
N16 C21 1.337(2) . ?
N16 C17 1.392(2) . ?
C17 C18 1.329(3) . ?
C17 H17 0.95 . ?
C18 N19 1.392(2) . ?
C18 H18 0.95 . ?
N19 C21 1.330(2) . ?
N19 C20 1.465(2) . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C21 C22 1.475(2) . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?


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
N4 Ni1 Cl1 100.90(4) . . ?
N4 Ni1 Cl2 112.10(4) . . ?
Cl1 Ni1 Cl2 111.659(18) . . ?
N4 Ni1 Cl3 109.30(4) . . ?
Cl1 Ni1 Cl3 122.493(18) . . ?
Cl2 Ni1 Cl3 100.687(17) . . ?
C7 N4 N5 105.71(12) . . ?
C7 N4 Ni1 125.86(11) . . ?
N5 N4 Ni1 128.38(10) . . ?
C9 N5 N4 110.82(13) . . ?
C9 N5 C11 126.81(14) . . ?
N4 N5 C11 122.37(12) . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 C8 110.15(15) . . ?
N4 C7 C6 122.47(15) . . ?
C8 C7 C6 127.36(15) . . ?
C9 C8 C7 106.27(15) . . ?
C9 C8 H8 126.9 . . ?
C7 C8 H8 126.9 . . ?
N5 C9 C8 107.05(14) . . ?
N5 C9 C10 122.60(15) . . ?
C8 C9 C10 130.33(16) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N5 C11 C12 113.00(13) . . ?
N5 C11 H11A 109 . . ?
C12 C11 H11A 109 . . ?
N5 C11 H11B 109 . . ?
C12 C11 H11B 109 . . ?
H11A C11 H11B 107.8 . . ?
O13 C12 C11 108.76(13) . . ?
O13 C12 H12A 109.9 . . ?
C11 C12 H12A 109.9 . . ?
O13 C12 H12B 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C14 O13 C12 112.24(12) . . ?
O13 C14 C15 108.01(14) . . ?
O13 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
O13 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
N16 C15 C14 110.67(13) . . ?
N16 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
N16 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C21 N16 C17 108.65(14) . . ?
C21 N16 C15 127.20(15) . . ?
C17 N16 C15 124.03(15) . . ?
C18 C17 N16 107.15(15) . . ?
C18 C17 H17 126.4 . . ?
N16 C17 H17 126.4 . . ?
C17 C18 N19 107.47(15) . . ?
C17 C18 H18 126.3 . . ?
N19 C18 H18 126.3 . . ?
C21 N19 C18 108.70(14) . . ?
C21 N19 C20 126.53(15) . . ?
C18 N19 C20 124.46(15) . . ?
N19 C20 H20A 109.5 . . ?
N19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N19 C21 N16 107.99(15) . . ?
N19 C21 C22 125.39(16) . . ?
N16 C21 C22 126.60(16) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 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
Cl1 Ni1 N4 C7 -85.23(13) . . . . ?
Cl2 Ni1 N4 C7 155.83(12) . . . . ?
Cl3 Ni1 N4 C7 45.09(13) . . . . ?
Cl1 Ni1 N4 N5 91.85(12) . . . . ?
Cl2 Ni1 N4 N5 -27.08(13) . . . . ?
Cl3 Ni1 N4 N5 -137.83(11) . . . . ?
C7 N4 N5 C9 -0.32(17) . . . . ?
Ni1 N4 N5 C9 -177.86(11) . . . . ?
C7 N4 N5 C11 179.37(13) . . . . ?
Ni1 N4 N5 C11 1.8(2) . . . . ?
N5 N4 C7 C8 0.77(17) . . . . ?
Ni1 N4 C7 C8 178.39(11) . . . . ?
N5 N4 C7 C6 -177.52(15) . . . . ?
Ni1 N4 C7 C6 0.1(2) . . . . ?
N4 C7 C8 C9 -0.93(19) . . . . ?
C6 C7 C8 C9 177.25(17) . . . . ?
N4 N5 C9 C8 -0.26(18) . . . . ?
C11 N5 C9 C8 -179.93(15) . . . . ?
N4 N5 C9 C10 178.20(15) . . . . ?
C11 N5 C9 C10 -1.5(3) . . . . ?
C7 C8 C9 N5 0.70(18) . . . . ?
C7 C8 C9 C10 -177.59(18) . . . . ?
C9 N5 C11 C12 106.89(18) . . . . ?
N4 N5 C11 C12 -72.75(18) . . . . ?
N5 C11 C12 O13 -55.50(17) . . . . ?
C11 C12 O13 C14 174.79(13) . . . . ?
C12 O13 C14 C15 -153.25(13) . . . . ?
O13 C14 C15 N16 63.38(18) . . . . ?
C14 C15 N16 C21 85.1(2) . . . . ?
C14 C15 N16 C17 -90.50(19) . . . . ?
C21 N16 C17 C18 1.01(19) . . . . ?
C15 N16 C17 C18 177.31(15) . . . . ?
N16 C17 C18 N19 0.00(19) . . . . ?
C17 C18 N19 C21 -1.01(19) . . . . ?
C17 C18 N19 C20 -175.01(15) . . . . ?
C18 N19 C21 N16 1.63(18) . . . . ?
C20 N19 C21 N16 175.48(15) . . . . ?
C18 N19 C21 C22 -177.24(16) . . . . ?
C20 N19 C21 C22 -3.4(3) . . . . ?
C17 N16 C21 N19 -1.64(18) . . . . ?
C15 N16 C21 N19 -177.79(15) . . . . ?
C17 N16 C21 C22 177.22(16) . . . . ?
C15 N16 C21 C22 1.1(3) . . . . ?


