# 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_km555se_0m
_database_code_depnum_ccdc_archive 'CCDC 1891631'
loop_
_audit_author_name
_audit_author_address
'Claire Wilson'
;University of Glasgow
United Kingdom
;
_audit_update_record             
;
2019-01-17 deposited with the CCDC.	2019-05-20 downloaded from the CCDC.
;
_audit_creation_date             2015-10-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H25 Cl3 Co1 N4'
_chemical_formula_sum            'C12 H25 Cl3 Co N4'
_chemical_formula_weight         390.64
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           155
_space_group_name_H-M_alt        'R 3 2'
_space_group_name_Hall           'R 3 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'

_cell_length_a                   10.581(3)
_cell_length_b                   10.581(3)
_cell_length_c                   12.329(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1195.4(6)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    1597
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.21
_cell_measurement_theta_min      2.77
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.575
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1131 before and 0.0922 after correction.
The Ratio of minimum to maximum transmission is 0.7196.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             609
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0875
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5214
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.442
_diffrn_reflns_theta_min         2.770
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                575
_reflns_number_total             607
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     33
_refine_ls_number_reflns         607
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0283P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0674
_refine_special_details          ?
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.98(4) 0.02(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
3. Others
 Fixed Sof: H2(0.16667)
4.a Ternary CH refined with riding coordinates:
 N2(H2)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C1(H1A,H1B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Co1 Co 0.3333 0.6667 0.6667 0.0093(4) Uani 1 6 d S T P . .
Cl1 Cl 0.55309(12) 0.6667 0.6667 0.0144(4) Uani 1 2 d S T P . .
N2 N 0.3333 0.6667 0.2737(4) 0.0119(11) Uani 1 3 d S T P . .
H2 H 0.3333 0.6667 0.1926 0.014 Uiso 0.5 3 calc RS T P . .
N1 N 0.3333 0.6667 0.4827(4) 0.0113(11) Uani 1 3 d S T P . .
C2 C 0.2209(4) 0.6995(4) 0.3153(3) 0.0125(9) Uani 1 1 d . . . . .
H2A H 0.1259 0.6345 0.2802 0.015 Uiso 1 1 calc R . . . .
H2B H 0.2494 0.8017 0.2983 0.015 Uiso 1 1 calc R . . . .
C1 C 0.2073(4) 0.6757(4) 0.4398(3) 0.0135(9) Uani 1 1 d . . . . .
H1A H 0.2031 0.7576 0.4751 0.016 Uiso 1 1 calc R . . . .
H1B H 0.1157 0.5844 0.4568 0.016 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Co1 0.0096(5) 0.0096(5) 0.0087(6) 0.000 0.000 0.0048(2)
Cl1 0.0130(6) 0.0207(8) 0.0120(7) -0.0001(5) 0.0000(3) 0.0103(4)
N2 0.0126(17) 0.0126(17) 0.010(2) 0.000 0.000 0.0063(8)
N1 0.0106(16) 0.0106(16) 0.013(3) 0.000 0.000 0.0053(8)
C2 0.0156(19) 0.015(2) 0.0102(16) -0.0016(15) -0.0008(14) 0.0105(17)
C1 0.0130(19) 0.019(2) 0.0102(19) -0.0009(15) -0.0008(15) 0.0095(15)

_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
Co1 Cl1 2.3252(14) . ?
Co1 Cl1 2.3253(14) 2_665 ?
Co1 Cl1 2.3253(14) 3_565 ?
Co1 N1 2.268(5) 10_456 ?
Co1 N1 2.268(5) . ?
N2 H2 1.0000 . ?
N2 C2 1.487(4) . ?
N2 C2 1.487(4) 3_565 ?
N2 C2 1.487(4) 2_665 ?
N1 C1 1.482(4) 3_565 ?
N1 C1 1.482(4) 2_665 ?
N1 C1 1.482(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.550(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?

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
Cl1 Co1 Cl1 120.000(1) 2_665 . ?
Cl1 Co1 Cl1 120.0 2_665 3_565 ?
Cl1 Co1 Cl1 120.0 3_565 . ?
N1 Co1 Cl1 90.001(1) . 3_565 ?
N1 Co1 Cl1 89.999(1) 10_456 3_565 ?
N1 Co1 Cl1 90.000 10_456 . ?
N1 Co1 Cl1 90.0 10_456 2_665 ?
N1 Co1 Cl1 90.0 . 2_665 ?
N1 Co1 Cl1 90.000 . . ?
N1 Co1 N1 180.0 10_456 . ?
C2 N2 H2 110.2 . . ?
C2 N2 H2 110.2 3_565 . ?
C2 N2 H2 110.2 2_665 . ?
C2 N2 C2 108.7(2) . 3_565 ?
C2 N2 C2 108.7(2) . 2_665 ?
C2 N2 C2 108.7(2) 3_565 2_665 ?
C1 N1 Co1 110.9(2) . . ?
C1 N1 Co1 110.9(2) 2_665 . ?
C1 N1 Co1 110.9(2) 3_565 . ?
C1 N1 C1 108.0(2) 3_565 2_665 ?
C1 N1 C1 108.0(2) . 3_565 ?
C1 N1 C1 108.0(2) . 2_665 ?
N2 C2 H2A 109.9 . . ?
N2 C2 H2B 109.9 . . ?
N2 C2 C1 108.9(3) . . ?
H2A C2 H2B 108.3 . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
N1 C1 C2 110.5(3) . . ?
N1 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
C2 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?

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
Co1 N1 C1 C2 171.3(2) . . . . ?
N2 C2 C1 N1 14.9(4) . . . . ?
C2 N2 C2 C1 50.6(4) 2_665 . . . ?
C2 N2 C2 C1 -67.6(3) 3_565 . . . ?
C1 N1 C1 C2 -66.9(3) 2_665 . . . ?
C1 N1 C1 C2 49.6(4) 3_565 . . . ?

_shelx_res_file                  
;
    km555se_0m.res created by SHELXL-2014/7

TITL km555se_0m_a.res in R32
REM Old TITL KM555se_0m in R32 #155
REM SHELXT solution in R32
REM R1 0.054, Rweak 0.061, Alpha 0.005, Orientation as input
REM Flack x = 0.016 ( 0.022 ) from Parsons' quotients
REM Formula found by SHELXT: C16 Cl3 Co
CELL 0.71075 10.5812 10.5812 12.3289 90 90 120
ZERR 3 0.0025 0.0025 0.0032 0 0 0
LATT -3
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SYMM +Y,+X,-Z
SYMM -Y+X,-Y,-Z
SYMM -X,-X+Y,-Z
SFAC C H Cl Co N
UNIT 36 75 9 3 12

L.S. 5 0 0
PLAN  20
TEMP -173(2)
BOND $H
LIST 6
MORE -1
CONF
fmap 2 53
ACTA
SHEL 100 0.77
TWIN -1 0 0 0 -1 0 0 0 -1 2
REM <olex2.extras>
REM <HklSrc "%.\\KM555se_0m.hkl">
REM </olex2.extras>

WGHT    0.028300
BASF   0.02135
FVAR       0.40221
CO1   4    0.333333    0.666667    0.666667    10.16667    0.00958    0.00958 =
         0.00869    0.00000    0.00000    0.00479
CL1   3    0.553085    0.666667    0.666667    10.50000    0.01300    0.02066 =
         0.01195   -0.00010   -0.00005    0.01033
N2    5    0.333333    0.666667    0.273704    10.33333    0.01262    0.01262 =
         0.01037    0.00000    0.00000    0.00631
AFIX  13
H2    2    0.333332    0.666667    0.192594    10.16667   -1.20000
AFIX   0
N1    5    0.333333    0.666667    0.482695    10.33333    0.01055    0.01055 =
         0.01272    0.00000    0.00000    0.00528
C2    1    0.220935    0.699462    0.315336    11.00000    0.01556    0.01540 =
         0.01024   -0.00164   -0.00082    0.01051
AFIX  23
H2A   2    0.125888    0.634492    0.280221    11.00000   -1.20000
H2B   2    0.249366    0.801727    0.298280    11.00000   -1.20000
AFIX   0
C1    1    0.207287    0.675698    0.439785    11.00000    0.01296    0.01938 =
         0.01016   -0.00093   -0.00084    0.00951
AFIX  23
H1A   2    0.203139    0.757578    0.475095    11.00000   -1.20000
H1B   2    0.115720    0.584399    0.456817    11.00000   -1.20000
AFIX   0
HKLF 4

REM  km555se_0m_a.res in R32
REM R1 =  0.0376 for     575 Fo > 4sig(Fo)  and  0.0453 for all     607 data
REM     33 parameters refined using      0 restraints

END

WGHT      0.0283      0.0000

REM Highest difference peak  0.489,  deepest hole -0.416,  1-sigma level  0.107
Q1    1   0.4626  0.7111  0.6759  11.00000  0.05    0.49
Q2    1   0.5408  0.6096  0.5946  11.00000  0.05    0.45
Q3    1   0.5435  0.8022  0.7134  11.00000  0.05    0.41
Q4    1   0.2982  0.7039  0.6131  11.00000  0.05    0.40
Q5    1   0.4683  0.4948  0.6411  11.00000  0.05    0.40
Q6    1   0.0774  0.5556  0.3841  11.00000  0.05    0.39
Q7    1   0.0228  0.4894  0.2881  11.00000  0.05    0.39
Q8    1   0.5171  0.7396  0.6844  11.00000  0.05    0.37
Q9    1   0.0543  0.5032  0.3643  11.00000  0.05    0.36
Q10   1   0.1634  0.6194  0.3788  11.00000  0.05    0.36
Q11   1   0.2130  0.6667  0.6667  10.50000  0.05    0.36
Q12   1   0.2207  0.7083  0.3817  11.00000  0.05    0.35
Q13   1   0.5900  0.5933  0.6743  11.00000  0.05    0.35
Q14   1   0.1500  0.6837  0.5095  11.00000  0.05    0.35
Q15   1   0.3365  0.9029  0.3802  11.00000  0.05    0.35
Q16   1   0.2959  0.7992  0.3756  11.00000  0.05    0.33
Q17   1  -0.0593  0.5328  0.2895  11.00000  0.05    0.33
Q18   1   0.5848  0.7509  0.6024  11.00000  0.05    0.32
Q19   1   0.6105  0.7740  0.6767  11.00000  0.05    0.32
Q20   1   0.6758  0.6667  0.6667  10.50000  0.05    0.32
;
_shelx_res_checksum              14555
_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.98(4)
2 0.02(4)

