# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

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

data_8jand
_database_code_depnum_ccdc_archive 'CCDC 1828731'
_audit_update_record             
;
2018-03-09 deposited with the CCDC.
2018-05-16 downloaded from the CCDC.
;
_audit_creation_date             2018-01-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5227)
;
_chemical_formula_moiety         'C17 H14 Br2 Co N4, H2 O'
_chemical_formula_sum            'C17 H16 Br2 Co N4 O'
_chemical_formula_weight         511.08
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Co 0.35655 0.96576 12.28410 7.34090 4.00340 2.34880 4.27910 0.27840 13.53590
71.16920 1.01180005074
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.8812(4)
_cell_length_b                   17.0462(7)
_cell_length_c                   11.8893(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.1423(13)
_cell_angle_gamma                90
_cell_volume                     1789.60(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9996
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.60
_exptl_absorpt_coefficient_mu    5.437
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5593
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0960 before and 0.0377 after correction.
The Ratio of minimum to maximum transmission is 0.7500.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.8968
_exptl_crystal_description       plate
_exptl_crystal_F_000             1003.6003
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.009
_exptl_crystal_size_min          0.005
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            28576
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.95
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                4065
_reflns_number_total             4441
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.5318
_refine_diff_density_min         -0.5362
_refine_diff_density_rms         0.0842
_refine_ls_d_res_high            0.7495
_refine_ls_d_res_low             6.9135
_refine_ls_goodness_of_fit_ref   1.0321
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     232
_refine_ls_number_reflns         4441
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0228
_refine_ls_R_factor_gt           0.0197
_refine_ls_restrained_S_all      1.0321
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0170P)²+1.8290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0448
_refine_ls_wR_factor_ref         0.0460
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O5aa(H5ab,H5ac)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C2aa(H2aa), C0aa(H0aa), C2(H2), N5aa(H5aa), C6aa(H6aa), C8(H8),
 C9(H9), C4(H4), C5(H5a), C6(H6)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Br2 Br 0.66528(2) 0.736228(10) 0.720453(16) 0.02041(5) Uani 1.000000 .
Co3 Co 0.63202(3) 0.597924(13) 0.779205(19) 0.01183(5) Uani 1.000000 .
C3 C 0.1263(2) 0.62306(12) 0.41012(15) 0.0209(4) Uani 1.000000 .
H3 H 0.0438(2) 0.63541(12) 0.35544(15) 0.0251(5) Uiso 1.000000 R
C1aa C 0.36449(19) 0.59183(11) 0.57354(14) 0.0143(3) Uani 1.000000 .
C1 C 0.26862(19) 0.53195(11) 0.52751(14) 0.0145(3) Uani 1.000000 .
C2aa C 0.3443(2) 0.66884(11) 0.53514(15) 0.0184(4) Uani 1.000000 .
H2aa H 0.4102(2) 0.70972(11) 0.56390(15) 0.0221(4) Uiso 1.000000 R
C0aa C 0.2240(2) 0.68339(12) 0.45321(16) 0.0214(4) Uani 1.000000 .
H0aa H 0.2073(2) 0.73532(12) 0.42564(16) 0.0257(5) Uiso 1.000000 R
C2 C 0.1476(2) 0.54635(12) 0.44538(15) 0.0181(4) Uani 1.000000 .
H2 H 0.0829(2) 0.50537(12) 0.41520(15) 0.0217(4) Uiso 1.000000 R
N5aa N 0.32019(16) 0.46341(9) 0.58162(12) 0.0150(3) Uani 1.000000 .
H5aa H 0.28195(16) 0.41613(9) 0.56981(12) 0.0180(3) Uiso 1.000000 R
N5 N 0.62323(16) 0.47076(9) 0.81886(13) 0.0131(3) Uani 1.000000 .
N7aa N 0.47143(16) 0.55887(9) 0.65514(12) 0.0133(3) Uani 1.000000 .
C3aa C 0.43968(18) 0.48289(10) 0.65552(14) 0.0129(3) Uani 1.000000 .
C4aa C 0.77462(19) 0.44034(11) 0.84604(14) 0.0142(3) Uani 1.000000 .
C12 C 0.53112(19) 0.42599(10) 0.72952(15) 0.0152(3) Uani 1.000000 .
H12a H 0.59794(19) 0.39540(10) 0.68437(15) 0.0183(4) Uiso 1.000000 R
H12b H 0.46348(19) 0.38902(10) 0.76412(15) 0.0183(4) Uiso 1.000000 R
C13 C 0.89466(19) 0.49294(11) 0.83509(14) 0.0145(3) Uani 1.000000 .
C6aa C 0.8044(2) 0.36440(11) 0.87981(16) 0.0199(4) Uani 1.000000 .
H6aa H 0.7231(2) 0.32907(11) 0.88646(16) 0.0239(4) Uiso 1.000000 R
C7 C 1.0463(2) 0.46681(12) 0.86004(15) 0.0188(4) Uani 1.000000 .
C8 C 1.0731(2) 0.38830(13) 0.89582(16) 0.0230(4) Uani 1.000000 .
H8 H 1.1740(2) 0.37028(13) 0.91372(16) 0.0276(5) Uiso 1.000000 R
C9 C 0.9553(2) 0.33859(13) 0.90471(17) 0.0240(4) Uani 1.000000 .
H9 H 0.9747(2) 0.28590(13) 0.92793(17) 0.0288(5) Uiso 1.000000 R
N6 N 0.86067(16) 0.56774(9) 0.79826(12) 0.0150(3) Uani 1.000000 .
C4 C 1.1628(2) 0.52103(13) 0.84686(17) 0.0246(4) Uani 1.000000 .
H4 H 1.2657(2) 0.50626(13) 0.86488(17) 0.0296(5) Uiso 1.000000 R
C5 C 0.9745(2) 0.61626(12) 0.78479(17) 0.0216(4) Uani 1.000000 .
H5a H 0.9515(2) 0.66788(12) 0.75813(17) 0.0259(5) Uiso 1.000000 R
C6 C 1.1276(2) 0.59460(13) 0.80826(19) 0.0267(4) Uani 1.000000 .
H6 H 1.2056(2) 0.63104(13) 0.79725(19) 0.0320(5) Uiso 1.000000 R
Br1 Br 0.525758(19) 0.623752(10) 0.958605(14) 0.01434(5) Uani 1.000000 .
O5aa O 0.22646(16) 0.31241(8) 0.52864(12) 0.0228(3) Uani 1.000000 .
H5ab H 0.254(3) 0.2806(10) 0.5844(11) 0.0343(4) Uiso 1.000000 G
H5ac H 0.262(3) 0.2957(12) 0.4677(10) 0.0343(4) Uiso 1.000000 G
H5 H 0.581(2) 0.4700(13) 0.8803(19) 0.017(5) Uiso 1.000000 .


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
Br2 Co3 2.4854(3) . ?
Co3 N5 2.2216(15) . ?
Co3 N7aa 2.0501(15) . ?
Co3 N6 2.0836(15) . ?
Co3 Br1 2.4627(3) . ?
C3 H3 0.9500 . ?
C3 C0aa 1.406(3) . ?
C3 C2 1.380(3) . ?
C1aa C1 1.402(2) . ?
C1aa C2aa 1.395(3) . ?
C1aa N7aa 1.401(2) . ?
C1 C2 1.395(2) . ?
C1 N5aa 1.388(2) . ?
C2aa H2aa 0.9500 . ?
C2aa C0aa 1.389(3) . ?
C0aa H0aa 0.9500 . ?
C2 H2 0.9500 . ?
N5aa H5aa 0.8800 . ?
N5aa C3aa 1.345(2) . ?
N5 C4aa 1.445(2) . ?
N5 C12 1.481(2) . ?
N5 H5 0.86(2) . ?
N7aa C3aa 1.326(2) . ?
C3aa C12 1.491(2) . ?
C4aa C13 1.410(2) . ?
C4aa C6aa 1.373(3) . ?
C12 H12a 0.9900 . ?
C12 H12b 0.9900 . ?
C13 C7 1.419(2) . ?
C13 N6 1.371(2) . ?
C6aa H6aa 0.9500 . ?
C6aa C9 1.411(3) . ?
C7 C8 1.417(3) . ?
C7 C4 1.409(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.359(3) . ?
C9 H9 0.9500 . ?
N6 C5 1.329(2) . ?
C4 H4 0.9500 . ?
C4 C6 1.360(3) . ?
C5 H5a 0.9500 . ?
C5 C6 1.408(3) . ?
C6 H6 0.9500 . ?
O5aa H5ab 0.8699 . ?
O5aa H5ac 0.8700 . ?

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
N5 Co3 Br2 173.29(4) . . ?
N7aa Co3 Br2 101.55(4) . . ?
N7aa Co3 N5 78.36(6) . . ?
N6 Co3 Br2 96.95(4) . . ?
N6 Co3 N5 77.99(6) . . ?
N6 Co3 N7aa 126.37(6) . . ?
Br1 Co3 Br2 98.158(10) . . ?
Br1 Co3 N5 88.01(4) . . ?
Br1 Co3 N7aa 112.31(4) . . ?
Br1 Co3 N6 114.16(4) . . ?
C0aa C3 H3 119.22(11) . . ?
C2 C3 H3 119.22(11) . . ?
C2 C3 C0aa 121.57(17) . . ?
C2aa C1aa C1 120.39(16) . . ?
N7aa C1aa C1 108.47(15) . . ?
N7aa C1aa C2aa 131.14(16) . . ?
C2 C1 C1aa 122.38(17) . . ?
N5aa C1 C1aa 105.99(15) . . ?
N5aa C1 C2 131.62(17) . . ?
H2aa C2aa C1aa 121.31(10) . . ?
C0aa C2aa C1aa 117.37(17) . . ?
C0aa C2aa H2aa 121.31(11) . . ?
C2aa C0aa C3 121.54(18) . . ?
H0aa C0aa C3 119.23(11) . . ?
H0aa C0aa C2aa 119.23(11) . . ?
C1 C2 C3 116.71(17) . . ?
H2 C2 C3 121.65(11) . . ?
H2 C2 C1 121.65(11) . . ?
H5aa N5aa C1 126.48(9) . . ?
C3aa N5aa C1 107.04(15) . . ?
C3aa N5aa H5aa 126.48(10) . . ?
C4aa N5 Co3 110.16(11) . . ?
C12 N5 Co3 112.32(10) . . ?
C12 N5 C4aa 113.88(14) . . ?
H5 N5 Co3 103.0(15) . . ?
H5 N5 C4aa 106.5(14) . . ?
H5 N5 C12 110.2(14) . . ?
C1aa N7aa Co3 137.40(12) . . ?
C3aa N7aa Co3 116.53(12) . . ?
C3aa N7aa C1aa 105.40(14) . . ?
N7aa C3aa N5aa 113.10(15) . . ?
C12 C3aa N5aa 124.53(15) . . ?
C12 C3aa N7aa 122.36(15) . . ?
C13 C4aa N5 116.48(15) . . ?
C6aa C4aa N5 123.33(16) . . ?
C6aa C4aa C13 120.18(16) . . ?
C3aa C12 N5 108.19(14) . . ?
H12a C12 N5 110.06(9) . . ?
H12a C12 C3aa 110.06(9) . . ?
H12b C12 N5 110.06(9) . . ?
H12b C12 C3aa 110.06(9) . . ?
H12b C12 H12a 108.4 . . ?
C7 C13 C4aa 119.43(17) . . ?
N6 C13 C4aa 118.56(15) . . ?
N6 C13 C7 122.00(16) . . ?
H6aa C6aa C4aa 119.85(11) . . ?
C9 C6aa C4aa 120.30(18) . . ?
C9 C6aa H6aa 119.85(12) . . ?
C8 C7 C13 118.95(17) . . ?
C4 C7 C13 117.57(18) . . ?
C4 C7 C8 123.47(17) . . ?
H8 C8 C7 119.78(11) . . ?
C9 C8 C7 120.43(17) . . ?
C9 C8 H8 119.78(11) . . ?
C8 C9 C6aa 120.71(19) . . ?
H9 C9 C6aa 119.65(12) . . ?
H9 C9 C8 119.65(11) . . ?
C13 N6 Co3 116.29(11) . . ?
C5 N6 Co3 125.32(13) . . ?
C5 N6 C13 118.23(16) . . ?
H4 C4 C7 120.10(12) . . ?
C6 C4 C7 119.80(18) . . ?
C6 C4 H4 120.10(11) . . ?
H5a C5 N6 118.53(11) . . ?
C6 C5 N6 122.94(19) . . ?
C6 C5 H5a 118.53(12) . . ?
C5 C6 C4 119.42(18) . . ?
H6 C6 C4 120.29(11) . . ?
H6 C6 C5 120.29(12) . . ?
H5ac O5aa H5ab 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
