# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_Ni(C6H3-4-OMe-2-Me)Br(L5)
_database_code_depnum_ccdc_archive 'CCDC 1852145'
_audit_update_record             
;
2018-06-28 deposited with the CCDC.
2018-11-26 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C20 H17 Br N2 Ni O'
_chemical_formula_moiety         'C20 H17 Br N2 Ni O'
_chemical_formula_weight         439.97
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
_space_group_IT_number           9
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 +X,-Y,1/2+Z
3 1/2+X,1/2+Y,+Z
4 1/2+X,1/2-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   11.964(13)
_cell_length_b                   20.02(2)
_cell_length_c                   7.423(11)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.11(4)
_cell_angle_gamma                90.0000
_cell_volume                     1778(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    977
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      25.90
_cell_measurement_temperature    113
#------------------------------------------------------------------------------
_exptl_crystal_description       chip
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888.00
_exptl_absorpt_coefficient_mu    3.355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.606
_exptl_absorpt_correction_T_max  0.935

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

_diffrn_ambient_temperature      113
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.814
_diffrn_reflns_number            21939
_diffrn_reflns_av_R_equivalents  0.1996
_diffrn_reflns_theta_max         27.738
_diffrn_reflns_theta_min         3.384
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4057
_reflns_number_gt                2441
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.946
_reflns_Friedel_fraction_max     0.945
_reflns_Friedel_fraction_full    0.971

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

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1249
_refine_ls_R_factor_gt           0.0728
_refine_ls_wR_factor_ref         0.1807
_refine_ls_wR_factor_gt          0.1620
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4057
_refine_ls_number_parameters     228
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0992P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.38
_refine_diff_density_min         -0.97
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 864 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(3)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Ni Ni 0.3393 1.1124
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
BR1 Br 0.23557(13) 0.66358(7) 0.66732(18) 0.0384(5) Uani 1 1 d . . . . .
NI1 Ni 0.41306(13) 0.64465(8) 0.5510(2) 0.0294(5) Uani 1 1 d . . . . .
O1 O 0.5514(9) 0.9389(5) 0.6090(17) 0.054(3) Uani 1 1 d . . . . .
N1 N 0.5577(9) 0.6275(6) 0.4413(16) 0.028(3) Uani 1 1 d . . . . .
N2 N 0.4014(9) 0.5443(5) 0.5534(17) 0.028(2) Uani 1 1 d . . . . .
C1 C 0.6350(12) 0.6705(7) 0.385(2) 0.033(3) Uani 1 1 d . . . . .
H1 H 0.620578 0.716942 0.398341 0.040 Uiso 1 1 calc R U . . .
C2 C 0.7377(14) 0.6508(7) 0.306(2) 0.038(4) Uani 1 1 d . . . . .
H2 H 0.788843 0.683539 0.263978 0.046 Uiso 1 1 calc R U . . .
C3 C 0.7631(11) 0.5836(7) 0.290(2) 0.032(3) Uani 1 1 d . . . . .
H3 H 0.832238 0.569580 0.239541 0.038 Uiso 1 1 calc R U . . .
C4 C 0.6820(9) 0.5357(6) 0.3505(18) 0.022(3) Uani 1 1 d . . . . .
C5 C 0.6951(11) 0.4640(7) 0.3362(19) 0.028(3) Uani 1 1 d . . . . .
H5 H 0.761103 0.446597 0.282866 0.034 Uiso 1 1 calc R U . . .
C6 C 0.6159(11) 0.4207(7) 0.3966(19) 0.029(3) Uani 1 1 d . . . . .
H6 H 0.629440 0.373996 0.392227 0.034 Uiso 1 1 calc R U . . .
C7 C 0.5115(11) 0.4454(6) 0.4672(18) 0.026(3) Uani 1 1 d . . . . .
C8 C 0.4221(12) 0.4052(6) 0.528(2) 0.031(3) Uani 1 1 d . . . . .
H8 H 0.427111 0.358019 0.516858 0.038 Uiso 1 1 calc R U . . .
C9 C 0.3289(13) 0.4328(7) 0.603(2) 0.034(3) Uani 1 1 d . . . . .
H9 H 0.270233 0.405259 0.646493 0.041 Uiso 1 1 calc R U . . .
C10 C 0.3211(14) 0.5037(7) 0.613(2) 0.033(3) Uani 1 1 d . . . . .
H10 H 0.256092 0.522844 0.665173 0.040 Uiso 1 1 calc R U . . .
C11 C 0.5811(11) 0.5597(6) 0.4200(19) 0.022(3) Uani 1 1 d . . . . .
C12 C 0.4969(11) 0.5147(6) 0.4822(18) 0.024(3) Uani 1 1 d . . . . .
C13 C 0.4411(12) 0.7384(7) 0.562(2) 0.038(4) Uani 1 1 d . . . . .
C14 C 0.4175(14) 0.7817(9) 0.430(2) 0.042(4) Uani 1 1 d . . . . .
C15 C 0.4570(14) 0.8510(8) 0.436(3) 0.040(4) Uani 1 1 d . . . . .
H15 H 0.442895 0.881184 0.340025 0.048 Uiso 1 1 calc R U . . .
C16 C 0.5138(12) 0.8701(8) 0.583(2) 0.039(4) Uani 1 1 d . . . . .
C17 C 0.5407(14) 0.8296(7) 0.727(2) 0.041(4) Uani 1 1 d . . . . .
H17 H 0.581949 0.845822 0.826874 0.049 Uiso 1 1 calc R U . . .
C18 C 0.5035(13) 0.7619(8) 0.717(3) 0.044(4) Uani 1 1 d . . . . .
H18 H 0.519624 0.732118 0.813509 0.053 Uiso 1 1 calc R U . . .
C19 C 0.3575(16) 0.7633(8) 0.266(3) 0.055(5) Uani 1 1 d . . . . .
H19A H 0.298792 0.731040 0.295859 0.066 Uiso 1 1 calc R U . . .
H19B H 0.409679 0.743308 0.180256 0.066 Uiso 1 1 calc R U . . .
H19C H 0.323709 0.803312 0.213029 0.066 Uiso 1 1 calc R U . . .
C20 C 0.5395(13) 0.9817(8) 0.455(3) 0.048(4) Uani 1 1 d . . . . .
H20A H 0.460020 0.987522 0.426743 0.057 Uiso 1 1 calc R U . . .
H20B H 0.577314 0.961428 0.351031 0.057 Uiso 1 1 calc R U . . .
H20C H 0.573156 1.025289 0.480519 0.057 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2016/4 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'

#==============================================================================
# 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
BR1 NI1 2.325(3) . ?
NI1 C13 1.908(14) . ?
NI1 N1 1.945(11) . ?
NI1 N2 2.014(11) . ?
O1 C20 1.44(2) . ?
O1 C16 1.463(19) . ?
N1 C1 1.332(19) . ?
N1 C11 1.393(16) . ?
N2 C10 1.335(19) . ?
N2 C12 1.392(17) . ?
C1 C2 1.42(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.38(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.438(17) . ?
C3 H3 0.9500 . ?
C4 C11 1.400(18) . ?
C4 C5 1.449(18) . ?
C5 C6 1.360(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.443(19) . ?
C6 H6 0.9500 . ?
C7 C12 1.404(18) . ?
C7 C8 1.413(18) . ?
C8 C9 1.36(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.42(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.428(17) . ?
C13 C14 1.34(2) . ?
C13 C18 1.45(3) . ?
C14 C19 1.45(3) . ?
C14 C15 1.47(2) . ?
C15 C16 1.34(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.38(2) . ?
C17 C18 1.43(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 NI1 N1 92.0(6) . . ?
C13 NI1 N2 173.2(6) . . ?
N1 NI1 N2 83.6(5) . . ?
C13 NI1 BR1 89.1(4) . . ?
N1 NI1 BR1 176.9(4) . . ?
N2 NI1 BR1 95.5(3) . . ?
C20 O1 C16 115.3(13) . . ?
C1 N1 C11 117.1(11) . . ?
C1 N1 NI1 129.4(9) . . ?
C11 N1 NI1 113.5(9) . . ?
C10 N2 C12 117.3(11) . . ?
C10 N2 NI1 131.4(10) . . ?
C12 N2 NI1 111.3(8) . . ?
N1 C1 C2 123.4(13) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C3 C2 C1 119.9(14) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 118.2(13) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C11 C4 C3 118.0(11) . . ?
C11 C4 C5 117.5(11) . . ?
C3 C4 C5 124.4(11) . . ?
C6 C5 C4 122.1(11) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 120.4(12) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C12 C7 C8 116.3(12) . . ?
C12 C7 C6 118.4(12) . . ?
C8 C7 C6 125.3(12) . . ?
C9 C8 C7 121.3(12) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 118.7(13) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
N2 C10 C9 122.8(14) . . ?
N2 C10 H10 118.6 . . ?
C9 C10 H10 118.6 . . ?
N1 C11 C4 123.3(12) . . ?
N1 C11 C12 115.8(12) . . ?
C4 C11 C12 120.8(11) . . ?
N2 C12 C7 123.6(11) . . ?
N2 C12 C11 115.7(10) . . ?
C7 C12 C11 120.7(11) . . ?
C14 C13 C18 118.7(15) . . ?
C14 C13 NI1 124.7(14) . . ?
C18 C13 NI1 116.3(11) . . ?
C13 C14 C19 123.4(16) . . ?
C13 C14 C15 121.4(17) . . ?
C19 C14 C15 115.1(16) . . ?
C16 C15 C14 117.3(16) . . ?
C16 C15 H15 121.3 . . ?
C14 C15 H15 121.3 . . ?
C15 C16 C17 125.4(16) . . ?
C15 C16 O1 122.0(14) . . ?
C17 C16 O1 112.5(15) . . ?
C16 C17 C18 116.7(16) . . ?
C16 C17 H17 121.6 . . ?
C18 C17 H17 121.6 . . ?
C17 C18 C13 120.4(16) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C1 C2 0(2) . . . . ?
NI1 N1 C1 C2 -179.7(12) . . . . ?
N1 C1 C2 C3 -2(2) . . . . ?
C1 C2 C3 C4 2(2) . . . . ?
C2 C3 C4 C11 1(2) . . . . ?
C2 C3 C4 C5 177.6(14) . . . . ?
C11 C4 C5 C6 -4(2) . . . . ?
C3 C4 C5 C6 179.8(14) . . . . ?
C4 C5 C6 C7 4(2) . . . . ?
C5 C6 C7 C12 -4(2) . . . . ?
C5 C6 C7 C8 177.9(14) . . . . ?
C12 C7 C8 C9 -2(2) . . . . ?
C6 C7 C8 C9 176.1(15) . . . . ?
C7 C8 C9 C10 2(2) . . . . ?
C12 N2 C10 C9 -2(2) . . . . ?
NI1 N2 C10 C9 -180.0(12) . . . . ?
C8 C9 C10 N2 0(3) . . . . ?
C1 N1 C11 C4 3(2) . . . . ?
NI1 N1 C11 C4 -177.5(10) . . . . ?
C1 N1 C11 C12 179.8(12) . . . . ?
NI1 N1 C11 C12 -0.4(16) . . . . ?
C3 C4 C11 N1 -3(2) . . . . ?
C5 C4 C11 N1 179.9(12) . . . . ?
C3 C4 C11 C12 179.8(12) . . . . ?
C5 C4 C11 C12 2.9(19) . . . . ?
C10 N2 C12 C7 1(2) . . . . ?
NI1 N2 C12 C7 -179.9(11) . . . . ?
C10 N2 C12 C11 -179.8(13) . . . . ?
NI1 N2 C12 C11 -1.1(15) . . . . ?
C8 C7 C12 N2 0(2) . . . . ?
C6 C7 C12 N2 -177.9(13) . . . . ?
C8 C7 C12 C11 -178.3(12) . . . . ?
C6 C7 C12 C11 3.3(19) . . . . ?
N1 C11 C12 N2 1.0(18) . . . . ?
C4 C11 C12 N2 178.2(13) . . . . ?
N1 C11 C12 C7 179.9(12) . . . . ?
C4 C11 C12 C7 -3(2) . . . . ?
C18 C13 C14 C19 178.8(14) . . . . ?
NI1 C13 C14 C19 6(2) . . . . ?
C18 C13 C14 C15 2(2) . . . . ?
NI1 C13 C14 C15 -170.4(11) . . . . ?
C13 C14 C15 C16 -3(2) . . . . ?
C19 C14 C15 C16 -179.3(14) . . . . ?
C14 C15 C16 C17 2(2) . . . . ?
C14 C15 C16 O1 -176.4(13) . . . . ?
C20 O1 C16 C15 -9.6(19) . . . . ?
C20 O1 C16 C17 172.0(13) . . . . ?
C15 C16 C17 C18 -1(2) . . . . ?
O1 C16 C17 C18 177.6(13) . . . . ?
C16 C17 C18 C13 0(2) . . . . ?
C14 C13 C18 C17 -1(2) . . . . ?
NI1 C13 C18 C17 172.1(11) . . . . ?

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

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


