# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_ACP1NI
_database_code_depnum_ccdc_archive 'CCDC 1407832'
_audit_update_record             
;
2015-06-19 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;

_audit_creation_date             2012-10-30T09:13:30-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H14 Cl N3 Ni'
_chemical_formula_sum            'C13 H14 Cl N3 Ni'
_chemical_formula_weight         306.43
_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                   7.8815(2)
_cell_length_b                   18.8766(5)
_cell_length_c                   8.5933(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.4990(10)
_cell_angle_gamma                90
_cell_volume                     1272.59(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8549
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.38
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    1.718
_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  0.807
_exptl_absorpt_correction_T_max  0.902


#----------------------------------------------------------------------------#
#                   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  0.0359
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_number            19895
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             2907
_reflns_number_gt                2526
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_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)+(0.0202P)²+0.8716P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2907
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.024
_refine_ls_wR_factor_ref         0.0565
_refine_ls_wR_factor_gt          0.0534
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.24
_refine_diff_density_rms         0.059


#----------------------------------------------------------------------------#
#                   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'
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 0.79541(2) 0.088581(10) 0.50088(2) 0.01449(7) Uani 1 1 d . . .
Cl1 Cl 0.54328(5) 0.08420(2) 0.37322(5) 0.02096(10) Uani 1 1 d . . .
N1 N 0.90721(17) 0.13040(7) 0.34167(16) 0.0175(3) Uani 1 1 d . . .
C2 C 0.8732(2) 0.15433(9) 0.1943(2) 0.0205(4) Uani 1 1 d . . .
H2 H 0.7667 0.1498 0.1332 0.025 Uiso 1 1 calc R . .
C3 C 1.0180(2) 0.18693(9) 0.1446(2) 0.0243(4) Uani 1 1 d . . .
H3 H 1.0269 0.2085 0.0459 0.029 Uiso 1 1 calc R . .
C4 C 1.1468(2) 0.18186(9) 0.2672(2) 0.0240(4) Uani 1 1 d . . .
H4 H 1.2604 0.1988 0.2679 0.029 Uiso 1 1 calc R . .
C5 C 1.0760(2) 0.14692(9) 0.3885(2) 0.0195(3) Uani 1 1 d . . .
C6 C 1.1284(2) 0.12394(9) 0.5425(2) 0.0218(4) Uani 1 1 d . . .
H6 H 1.2409 0.1304 0.5906 0.026 Uiso 1 1 calc R . .
N7 N 1.00906(18) 0.09314(7) 0.61252(17) 0.0195(3) Uani 1 1 d . . .
C8 C 1.0238(2) 0.06706(10) 0.7735(2) 0.0236(4) Uani 1 1 d . . .
H8A H 1.0211 0.1069 0.8481 0.028 Uiso 1 1 calc R . .
H8B H 1.1317 0.0407 0.7971 0.028 Uiso 1 1 calc R . .
C9 C 0.8719(2) 0.01865(9) 0.7843(2) 0.0213(4) Uani 1 1 d . . .
H9A H 0.8961 -0.0287 0.7423 0.026 Uiso 1 1 calc R . .
H9B H 0.8488 0.0131 0.8949 0.026 Uiso 1 1 calc R . .
N10 N 0.71934(17) 0.05066(7) 0.69134(16) 0.0163(3) Uani 1 1 d . . .
H10 H 0.650(3) 0.0172(13) 0.672(3) 0.05 Uiso 1 1 d . . .
C11 C 0.6315(2) 0.10243(8) 0.78153(19) 0.0157(3) Uani 1 1 d . . .
C12 C 0.5047(2) 0.07954(9) 0.8706(2) 0.0194(3) Uani 1 1 d . . .
H12 H 0.4738 0.0309 0.8708 0.023 Uiso 1 1 calc R . .
C13 C 0.4228(2) 0.12784(10) 0.9598(2) 0.0227(4) Uani 1 1 d . . .
H13 H 0.3363 0.1122 1.0216 0.027 Uiso 1 1 calc R . .
C14 C 0.4671(2) 0.19883(9) 0.9586(2) 0.0234(4) Uani 1 1 d . . .
H14 H 0.4111 0.2319 1.0197 0.028 Uiso 1 1 calc R . .
C15 C 0.5932(2) 0.22167(9) 0.8683(2) 0.0247(4) Uani 1 1 d . . .
H15 H 0.6227 0.2704 0.867 0.03 Uiso 1 1 calc R . .
C16 C 0.6764(2) 0.17362(9) 0.7799(2) 0.0207(4) Uani 1 1 d . . .
H16 H 0.7634 0.1893 0.7187 0.025 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 N7 1.8585(14) . ?
Ni1 N1 1.8715(14) . ?
Ni1 N10 1.9335(14) . ?
Ni1 Cl1 2.1774(4) . ?
N1 C2 1.347(2) . ?
N1 C5 1.388(2) . ?
C2 C3 1.399(2) . ?
C2 H2 0.95 . ?
C3 C4 1.394(3) . ?
C3 H3 0.95 . ?
C4 C5 1.395(2) . ?
C4 H4 0.95 . ?
C5 C6 1.416(2) . ?
C6 N7 1.301(2) . ?
C6 H6 0.95 . ?
N7 C8 1.462(2) . ?
C8 C9 1.516(2) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 N10 1.505(2) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
N10 C11 1.462(2) . ?
N10 H10 0.84(2) . ?
C11 C12 1.385(2) . ?
C11 C16 1.390(2) . ?
C12 C13 1.389(2) . ?
C12 H12 0.95 . ?
C13 C14 1.385(3) . ?
C13 H13 0.95 . ?
C14 C15 1.387(3) . ?
C14 H14 0.95 . ?
C15 C16 1.388(2) . ?
C15 H15 0.95 . ?
C16 H16 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
N7 Ni1 N1 83.74(6) . . ?
N7 Ni1 N10 85.37(6) . . ?
N1 Ni1 N10 168.77(6) . . ?
N7 Ni1 Cl1 179.04(5) . . ?
N1 Ni1 Cl1 96.81(4) . . ?
N10 Ni1 Cl1 94.04(4) . . ?
C2 N1 C5 107.24(14) . . ?
C2 N1 Ni1 139.76(12) . . ?
C5 N1 Ni1 112.83(11) . . ?
N1 C2 C3 109.85(15) . . ?
N1 C2 H2 125.1 . . ?
C3 C2 H2 125.1 . . ?
C4 C3 C2 107.21(16) . . ?
C4 C3 H3 126.4 . . ?
C2 C3 H3 126.4 . . ?
C3 C4 C5 106.41(15) . . ?
C3 C4 H4 126.8 . . ?
C5 C4 H4 126.8 . . ?
N1 C5 C4 109.28(15) . . ?
N1 C5 C6 112.81(15) . . ?
C4 C5 C6 137.91(16) . . ?
N7 C6 C5 114.22(15) . . ?
N7 C6 H6 122.9 . . ?
C5 C6 H6 122.9 . . ?
C6 N7 C8 126.34(15) . . ?
C6 N7 Ni1 116.18(12) . . ?
C8 N7 Ni1 117.29(11) . . ?
N7 C8 C9 105.64(14) . . ?
N7 C8 H8A 110.6 . . ?
C9 C8 H8A 110.6 . . ?
N7 C8 H8B 110.6 . . ?
C9 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
N10 C9 C8 108.70(13) . . ?
N10 C9 H9A 109.9 . . ?
C8 C9 H9A 109.9 . . ?
N10 C9 H9B 109.9 . . ?
C8 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C11 N10 C9 112.44(13) . . ?
C11 N10 Ni1 113.72(10) . . ?
C9 N10 Ni1 107.54(10) . . ?
C11 N10 H10 106.1(16) . . ?
C9 N10 H10 106.1(17) . . ?
Ni1 N10 H10 110.7(17) . . ?
C12 C11 C16 120.33(15) . . ?
C12 C11 N10 119.20(14) . . ?
C16 C11 N10 120.46(15) . . ?
C11 C12 C13 119.89(15) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 120.00(16) . . ?
C14 C13 H13 120 . . ?
C12 C13 H13 120 . . ?
C13 C14 C15 119.97(16) . . ?
C13 C14 H14 120 . . ?
C15 C14 H14 120 . . ?
C14 C15 C16 120.32(16) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 119.48(16) . . ?
C15 C16 H16 120.3 . . ?
C11 C16 H16 120.3 . . ?


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 Ni1 N1 C2 -178.67(18) . . . . ?
N10 Ni1 N1 C2 -164.4(2) . . . . ?
Cl1 Ni1 N1 C2 0.54(18) . . . . ?
N7 Ni1 N1 C5 -4.17(11) . . . . ?
N10 Ni1 N1 C5 10.1(4) . . . . ?
Cl1 Ni1 N1 C5 175.04(10) . . . . ?
C5 N1 C2 C3 -0.47(19) . . . . ?
Ni1 N1 C2 C3 174.22(14) . . . . ?
N1 C2 C3 C4 0.7(2) . . . . ?
C2 C3 C4 C5 -0.59(19) . . . . ?
C2 N1 C5 C4 0.10(19) . . . . ?
Ni1 N1 C5 C4 -176.19(11) . . . . ?
C2 N1 C5 C6 -179.60(14) . . . . ?
Ni1 N1 C5 C6 4.11(18) . . . . ?
C3 C4 C5 N1 0.31(19) . . . . ?
C3 C4 C5 C6 179.9(2) . . . . ?
N1 C5 C6 N7 -1.3(2) . . . . ?
C4 C5 C6 N7 179.1(2) . . . . ?
C5 C6 N7 C8 -177.05(15) . . . . ?
C5 C6 N7 Ni1 -2.2(2) . . . . ?
N1 Ni1 N7 C6 3.59(13) . . . . ?
N10 Ni1 N7 C6 -173.65(13) . . . . ?
N1 Ni1 N7 C8 178.97(13) . . . . ?
N10 Ni1 N7 C8 1.72(12) . . . . ?
C6 N7 C8 C9 -164.65(16) . . . . ?
Ni1 N7 C8 C9 20.50(17) . . . . ?
N7 C8 C9 N10 -38.81(18) . . . . ?
C8 C9 N10 C11 -85.03(17) . . . . ?
C8 C9 N10 Ni1 40.91(15) . . . . ?
N7 Ni1 N10 C11 101.34(11) . . . . ?
N1 Ni1 N10 C11 87.1(3) . . . . ?
Cl1 Ni1 N10 C11 -77.90(10) . . . . ?
N7 Ni1 N10 C9 -23.83(10) . . . . ?
N1 Ni1 N10 C9 -38.0(3) . . . . ?
Cl1 Ni1 N10 C9 156.93(9) . . . . ?
C9 N10 C11 C12 -88.38(18) . . . . ?
Ni1 N10 C11 C12 149.10(13) . . . . ?
C9 N10 C11 C16 90.65(18) . . . . ?
Ni1 N10 C11 C16 -31.86(19) . . . . ?
C16 C11 C12 C13 -0.5(2) . . . . ?
N10 C11 C12 C13 178.53(15) . . . . ?
C11 C12 C13 C14 0.5(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C11 0.5(3) . . . . ?
C12 C11 C16 C15 0.0(3) . . . . ?
N10 C11 C16 C15 -179.00(15) . . . . ?


loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N10 H10 Cl1 0.84(2) 2.45(3) 3.2944(14) 177(2) 3_656


