# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_17008
_database_code_depnum_ccdc_archive 'CCDC 1823665'
_audit_update_record             
;
2018-02-12 deposited with the CCDC.
2018-05-23 downloaded from the CCDC.
;
_audit_creation_date             2017-01-25
_audit_creation_method           CRYSTALS_ver_14.61_build_00000

_oxford_structure_analysis_title 'mo_17008_0m in R-3c'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_cell_length_a                   19.8350(5)
_cell_length_b                   19.8350(5)
_cell_length_c                   29.0373(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     9893.5(4)

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'R 3 c '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/3,y+2/3,z+2/3
x+2/3,y+1/3,z+1/3
-x+y,-x,z
-x+y+1/3,-x+2/3,z+2/3
-x+y+2/3,-x+1/3,z+1/3
x,x-y,z+1/2
x+1/3,x-y+2/3,z+7/6
x+2/3,x-y+1/3,z+5/6
-y,-x,z+1/2
-y+1/3,-x+2/3,z+7/6
-y+2/3,-x+1/3,z+5/6
-x+y,y,z+1/2
-x+y+1/3,y+2/3,z+7/6
-x+y+2/3,y+1/3,z+5/6
-y,x-y,z
-y+1/3,x-y+2/3,z+2/3
-y+2/3,x-y+1/3,z+1/3

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_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Co 0.3494 0.9721 12.2841 4.2791 7.3409 0.2784 4.0034 13.5359 2.3488 71.1692
1.0118 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            18

# Given Formula = C12 H24 Co0.50 N7 O9 
# Dc =      1.33 Fooo =   4149.00 Mu =      4.71 M =    439.83
# Found Formula = C12 H24 Co1 N7.00 O9 
# Dc =      1.42 FOOO =   4392.00 Mu =      8.36 M =    469.30

_chemical_formula_sum            'C12 H24 Co1 N7.00 O9'
_chemical_formula_moiety         'C12 H24 Co1 N7.00 O9'
_chemical_compound_source        ?
_chemical_formula_weight         469.30


_cell_measurement_reflns_used    9873
_cell_measurement_theta_min      3
_cell_measurement_theta_max      30
_cell_measurement_temperature    173

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_min          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_max          0.350

_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             4392.000
_exptl_absorpt_coefficient_mu    0.836

# Sheldrick geometric approximatio 0.78 0.78 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.78
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      173
_diffrn_reflns_number            5615
_reflns_number_total             5615
_diffrn_reflns_av_R_equivalents  0.021
# Number of reflections without Friedels Law is 5615 
# Number of reflections with Friedels Law is 3225 
# Theoretical number of reflections is about 3225 


_diffrn_reflns_theta_min         1.837
_diffrn_reflns_theta_max         30.062
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        30.062
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       34
_reflns_limit_h_min              -23
_reflns_limit_h_max              0
_reflns_limit_k_min              0
_reflns_limit_k_max              27
_reflns_limit_l_min              -40
_reflns_limit_l_max              34

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.55
_refine_diff_density_max         0.73


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         5601
_refine_ls_number_restraints     84
_refine_ls_number_parameters     286
_oxford_refine_ls_R_factor_ref   0.0515
_refine_ls_wR_factor_ref         0.1408
_refine_ls_goodness_of_fit_ref   1.0080
_refine_ls_shift/su_max          0.0457624
_refine_ls_shift/su_mean         0.0027188


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5601
_refine_ls_R_factor_all          0.0515
_refine_ls_wR_factor_all         0.1408

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                5261
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_gt          0.1386

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration unk


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.09P)² +27.74P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Co1 Co 0.51237(2) 0.49495(2) 0.61468(5) 0.0217 1.0000 Uani D . . . . .
O1 O 0.55432(15) 0.46756(16) 0.66624(8) 0.0349 1.0000 Uani D . . . . .
O2 O 0.56747(19) 0.4429(2) 0.73696(10) 0.0577 1.0000 Uani D . . . . .
O3 O 0.4775(3) 0.4686(4) 0.71947(17) 0.0695 0.604(8) Uani D . P 1 1 .
O4 O 0.46625(15) 0.50442(13) 0.55835(9) 0.0291 1.0000 Uani . . . . . .
O5 O 0.44789(19) 0.56160(18) 0.50111(12) 0.0483 1.0000 Uani . . . . . .
O6 O 0.55669(18) 0.62222(17) 0.53651(11) 0.0502 1.0000 Uani . . . . . .
O7 O 0.9053(4) 0.7195(3) 0.6377(2) 0.0739 0.742(11) Uani D U P 1 3 .
O8 O 0.8469(3) 0.7857(3) 0.64329(14) 0.0507 0.742(11) Uani D U P 1 3 .
O9 O 0.8662(3) 0.7533(3) 0.57746(16) 0.0713 0.742(11) Uani D U P 1 3 .
O31 O 0.5211 0.5159 0.7228 0.0548 0.396(8) Uiso D . P 1 2 .
O71 O 0.8580(10) 0.7887(10) 0.5867(4) 0.078(5) 0.258(11) Uiso D . P 1 4 .
O81 O 0.8985(11) 0.7109(10) 0.6099(6) 0.082(5) 0.258(11) Uiso D . P 1 4 .
O91 O 0.8663(12) 0.7679(11) 0.6592(3) 0.082(5) 0.258(11) Uiso D . P 1 4 .
N1 N 0.59800(15) 0.59977(15) 0.62208(10) 0.0275 1.0000 Uani . . . . . .
N2 N 0.45480(16) 0.53870(16) 0.64370(11) 0.0285 1.0000 Uani . . . . . .
N3 N 0.42673(16) 0.38651(16) 0.61566(10) 0.0276 1.0000 Uani D . . . . .
N4 N 0.49182(19) 0.56530(18) 0.53152(11) 0.0327 1.0000 Uani . . . . . .
N5 N 0.53393(17) 0.4629(2) 0.70870(10) 0.0319 0.604(8) Uani D . P 1 1 .
N6 N 0.87349(18) 0.75437(19) 0.61920(9) 0.0429 1.0000 Uani D U . . . .
N7 N 0.56792(16) 0.45541(16) 0.57793(11) 0.0263 1.0000 Uani D . . . . .
N51 N 0.5504(2) 0.47954(19) 0.70994(6) 0.0532(10) 0.396(8) Uiso D . P 1 2 .
C1 C 0.5803(2) 0.64699(19) 0.64185(11) 0.0270 1.0000 Uani . . . . . .
C2 C 0.4950(2) 0.6123(2) 0.65074(13) 0.0317 1.0000 Uani . . . . . .
C3 C 0.3698(2) 0.4991(2) 0.64886(14) 0.0366 1.0000 Uani . . . . . .
C4 C 0.3297(2) 0.4115(2) 0.65290(15) 0.0417 1.0000 Uani . . . . . .
C5 C 0.3458(2) 0.3719(2) 0.61284(14) 0.0369 1.0000 Uani D . . . . .
C6 C 0.4426(2) 0.3420(2) 0.58034(13) 0.0355 1.0000 Uani D . . . . .
C7 C 0.5277(2) 0.36966(19) 0.58335(13) 0.0335 1.0000 Uani D . . . . .
C8 C 0.6532(2) 0.4923(2) 0.58337(13) 0.0339 1.0000 Uani D . . . . .
C9 C 0.6919(2) 0.5790(2) 0.57451(14) 0.0341 1.0000 Uani . . . . . .
C10 C 0.68000(18) 0.6250(2) 0.61218(14) 0.0343 1.0000 Uani . . . . . .
C11 C 0.6350(2) 0.7285(2) 0.65560(14) 0.0379 1.0000 Uani . . . . . .
C12 C 0.4622(3) 0.6627(2) 0.66503(16) 0.0429 1.0000 Uani . . . . . .
H31 H 0.3583 0.5187 0.6758 0.0441 1.0000 Uiso R . . . . .
H32 H 0.3490 0.5111 0.6227 0.0441 1.0000 Uiso R . . . . .
H41 H 0.3476 0.3993 0.6803 0.0507 1.0000 Uiso R . . . . .
H42 H 0.2751 0.3914 0.6549 0.0507 1.0000 Uiso R . . . . .
H51 H 0.3105 0.3174 0.6140 0.0433 1.0000 Uiso R . . . . .
H52 H 0.3392 0.3923 0.5847 0.0433 1.0000 Uiso R . . . . .
H61 H 0.4135 0.2879 0.5869 0.0422 1.0000 Uiso R . . . . .
H62 H 0.4297 0.3515 0.5505 0.0422 1.0000 Uiso R . . . . .
H71 H 0.5400 0.3564 0.6124 0.0417 1.0000 Uiso R . . . . .
H72 H 0.5426 0.3470 0.5595 0.0417 1.0000 Uiso R . . . . .
H81 H 0.6648 0.4842 0.6139 0.0401 1.0000 Uiso R . . . . .
H82 H 0.6726 0.4694 0.5623 0.0401 1.0000 Uiso R . . . . .
H91 H 0.7462 0.5988 0.5708 0.0424 1.0000 Uiso R . . . . .
H92 H 0.6710 0.5865 0.5468 0.0424 1.0000 Uiso R . . . . .
H101 H 0.7029 0.6192 0.6395 0.0429 1.0000 Uiso R . . . . .
H102 H 0.7056 0.6783 0.6035 0.0429 1.0000 Uiso R . . . . .
H111 H 0.6075 0.7510 0.6694 0.0452 1.0000 Uiso R . . . . .
H112 H 0.6716 0.7291 0.6769 0.0452 1.0000 Uiso R . . . . .
H113 H 0.6616 0.7576 0.6290 0.0452 1.0000 Uiso R . . . . .
H121 H 0.4075 0.6313 0.6693 0.0544 1.0000 Uiso R . . . . .
H122 H 0.4858 0.6879 0.6932 0.0544 1.0000 Uiso R . . . . .
H123 H 0.4724 0.7007 0.6420 0.0544 1.0000 Uiso R . . . . .
H1 H 0.4313(13) 0.3666(14) 0.6432(7) 0.0342 1.0000 Uiso D . . . . .
H2 H 0.5625(13) 0.4649(14) 0.5485(7) 0.0314 1.0000 Uiso D . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.046333(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Co1 . O1 . 1.919(2) yes
Co1 . O4 . 1.928(2) yes
Co1 . N1 . 1.929(3) yes
Co1 . N2 . 1.939(3) yes
Co1 . N3 . 1.965(3) yes
Co1 . N7 . 1.958(3) yes
O1 . N5 . 1.287(3) yes
O1 . N51 . 1.300(3) yes
O2 . N5 . 1.241(3) yes
O2 . N51 . 1.227(3) yes
O3 . N5 . 1.220(4) yes
O4 . N4 . 1.308(4) yes
O5 . N4 . 1.217(4) yes
O6 . N4 . 1.224(4) yes
O7 . N6 . 1.265(5) yes
O8 . N6 . 1.217(4) yes
O9 . N6 . 1.220(5) yes
O31 . N51 . 1.190(2) yes
O71 . N6 . 1.288(7) yes
O81 . N6 . 1.222(7) yes
O91 . N6 . 1.217(7) yes
N1 . C1 . 1.288(4) yes
N1 . C10 . 1.472(4) yes
N2 . C2 . 1.282(4) yes
N2 . C3 . 1.470(4) yes
N3 . C5 . 1.483(5) yes
N3 . C6 . 1.486(4) yes
N3 . H1 . 0.915(19) no
N7 . C7 . 1.482(4) yes
N7 . C8 . 1.479(4) yes
N7 . H2 . 0.892(19) no
C1 . C2 . 1.495(5) yes
C1 . C11 . 1.482(5) yes
C2 . C12 . 1.500(5) yes
C3 . C4 . 1.511(6) yes
C3 . H31 . 0.950 no
C3 . H32 . 0.950 no
C4 . C5 . 1.524(6) yes
C4 . H41 . 0.950 no
C4 . H42 . 0.950 no
C5 . H51 . 0.950 no
C5 . H52 . 0.950 no
C6 . C7 . 1.493(5) yes
C6 . H61 . 0.950 no
C6 . H62 . 0.950 no
C7 . H71 . 0.950 no
C7 . H72 . 0.950 no
C8 . C9 . 1.514(5) yes
C8 . H81 . 0.950 no
C8 . H82 . 0.950 no
C9 . C10 . 1.516(5) yes
C9 . H91 . 0.950 no
C9 . H92 . 0.950 no
C10 . H101 . 0.950 no
C10 . H102 . 0.950 no
C11 . H111 . 0.950 no
C11 . H112 . 0.950 no
C11 . H113 . 0.950 no
C12 . H121 . 0.950 no
C12 . H122 . 0.950 no
C12 . H123 . 0.950 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . Co1 . O4 . 169.54(12) yes
O1 . Co1 . N1 . 86.87(11) yes
O4 . Co1 . N1 . 101.22(11) yes
O1 . Co1 . N2 . 102.91(12) yes
O4 . Co1 . N2 . 84.89(12) yes
N1 . Co1 . N2 . 82.38(12) yes
O1 . Co1 . N3 . 86.48(11) yes
O4 . Co1 . N3 . 85.77(11) yes
N1 . Co1 . N3 . 172.59(12) yes
N2 . Co1 . N3 . 95.93(12) yes
O1 . Co1 . N7 . 84.33(11) yes
O4 . Co1 . N7 . 88.06(12) yes
N1 . Co1 . N7 . 97.12(12) yes
N2 . Co1 . N7 . 172.69(13) yes
N3 . Co1 . N7 . 85.47(11) yes
Co1 . O1 . N5 . 127.06(16) yes
Co1 . O1 . N51 . 129.48(13) yes
Co1 . O4 . N4 . 127.7(2) yes
Co1 . N1 . C1 . 114.8(2) yes
Co1 . N1 . C10 . 124.9(2) yes
C1 . N1 . C10 . 119.8(3) yes
Co1 . N2 . C2 . 114.1(2) yes
Co1 . N2 . C3 . 125.5(2) yes
C2 . N2 . C3 . 119.2(3) yes
Co1 . N3 . C5 . 118.2(2) yes
Co1 . N3 . C6 . 108.4(2) yes
C5 . N3 . C6 . 112.1(3) yes
Co1 . N3 . H1 . 105.5(15) no
C5 . N3 . H1 . 107.2(14) no
C6 . N3 . H1 . 104.5(15) no
O4 . N4 . O6 . 121.7(3) yes
O4 . N4 . O5 . 116.2(3) yes
O6 . N4 . O5 . 122.2(3) yes
O1 . N5 . O2 . 117.20(5) yes
O1 . N5 . O3 . 120.61(5) yes
O2 . N5 . O3 . 121.58(5) yes
O7 . N6 . O9 . 120.02(6) yes
O7 . N6 . O8 . 119.75(6) yes
O9 . N6 . O8 . 120.14(6) yes
O71 . N6 . O81 . 119.97(6) yes
O71 . N6 . O91 . 119.92(6) yes
O81 . N6 . O91 . 120.03(6) yes
Co1 . N7 . C7 . 108.3(2) yes
Co1 . N7 . C8 . 118.5(2) yes
C7 . N7 . C8 . 112.5(3) yes
Co1 . N7 . H2 . 106.6(15) no
C7 . N7 . H2 . 107.0(15) no
C8 . N7 . H2 . 103.1(14) no
O1 . N51 . O2 . 117.17(5) yes
O1 . N51 . O31 . 120.54(5) yes
O2 . N51 . O31 . 121.45(5) yes
N1 . C1 . C2 . 113.5(3) yes
N1 . C1 . C11 . 126.6(3) yes
C2 . C1 . C11 . 119.9(3) yes
C1 . C2 . N2 . 114.4(3) yes
C1 . C2 . C12 . 120.6(3) yes
N2 . C2 . C12 . 124.9(3) yes
N2 . C3 . C4 . 115.2(3) yes
N2 . C3 . H31 . 108.1 no
C4 . C3 . H31 . 108.2 no
N2 . C3 . H32 . 108.0 no
C4 . C3 . H32 . 107.8 no
H31 . C3 . H32 . 109.5 no
C3 . C4 . C5 . 114.1(3) yes
C3 . C4 . H41 . 107.9 no
C5 . C4 . H41 . 107.9 no
C3 . C4 . H42 . 108.7 no
C5 . C4 . H42 . 108.7 no
H41 . C4 . H42 . 109.5 no
C4 . C5 . N3 . 110.0(3) yes
C4 . C5 . H51 . 109.5 no
N3 . C5 . H51 . 109.4 no
C4 . C5 . H52 . 109.1 no
N3 . C5 . H52 . 109.4 no
H51 . C5 . H52 . 109.5 no
N3 . C6 . C7 . 106.1(3) yes
N3 . C6 . H61 . 110.1 no
C7 . C6 . H61 . 109.9 no
N3 . C6 . H62 . 110.8 no
C7 . C6 . H62 . 110.4 no
H61 . C6 . H62 . 109.5 no
C6 . C7 . N7 . 106.0(3) yes
C6 . C7 . H71 . 110.4 no
N7 . C7 . H71 . 110.2 no
C6 . C7 . H72 . 110.2 no
N7 . C7 . H72 . 110.4 no
H71 . C7 . H72 . 109.5 no
N7 . C8 . C9 . 110.4(3) yes
N7 . C8 . H81 . 109.2 no
C9 . C8 . H81 . 108.8 no
N7 . C8 . H82 . 109.3 no
C9 . C8 . H82 . 109.7 no
H81 . C8 . H82 . 109.5 no
C8 . C9 . C10 . 114.7(3) yes
C8 . C9 . H91 . 108.3 no
C10 . C9 . H91 . 108.6 no
C8 . C9 . H92 . 108.0 no
C10 . C9 . H92 . 107.7 no
H91 . C9 . H92 . 109.5 no
C9 . C10 . N1 . 114.5(3) yes
C9 . C10 . H101 . 107.7 no
N1 . C10 . H101 . 108.1 no
C9 . C10 . H102 . 108.8 no
N1 . C10 . H102 . 108.3 no
H101 . C10 . H102 . 109.5 no
C1 . C11 . H111 . 110.3 no
C1 . C11 . H112 . 109.1 no
H111 . C11 . H112 . 109.5 no
C1 . C11 . H113 . 109.0 no
H111 . C11 . H113 . 109.5 no
H112 . C11 . H113 . 109.5 no
C2 . C12 . H121 . 109.4 no
C2 . C12 . H122 . 109.0 no
H121 . C12 . H122 . 109.5 no
C2 . C12 . H123 . 110.0 no
H121 . C12 . H123 . 109.5 no
H122 . C12 . H123 . 109.5 no

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
N1 Co1 O1 N5 95.7(3) . . . . no
N2 Co1 O1 N5 14.3(3) . . . . no
N3 Co1 O1 N5 -81.0(3) . . . . no
N7 Co1 O1 N5 -166.8(3) . . . . no
N1 Co1 O4 N4 4.7(3) . . . . no
N2 Co1 O4 N4 85.9(3) . . . . no
N3 Co1 O4 N4 -177.8(3) . . . . no
N7 Co1 O4 N4 -92.2(3) . . . . no
O1 Co1 N1 C1 -102.5(3) . . . . no
O1 Co1 N1 C10 69.8(3) . . . . no
O4 Co1 N1 C1 84.2(3) . . . . no
O4 Co1 N1 C10 -103.5(3) . . . . no
N2 Co1 N1 C1 1.0(3) . . . . no
N2 Co1 N1 C10 173.3(3) . . . . no
N7 Co1 N1 C1 173.7(3) . . . . no
N7 Co1 N1 C10 -14.1(3) . . . . no
O1 Co1 N2 C2 89.7(3) . . . . no
O1 Co1 N2 C3 -103.4(3) . . . . no
O4 Co1 N2 C2 -97.3(3) . . . . no
O4 Co1 N2 C3 69.6(3) . . . . no
N1 Co1 N2 C2 4.7(3) . . . . no
N1 Co1 N2 C3 171.6(3) . . . . no
N3 Co1 N2 C2 177.5(3) . . . . no
N3 Co1 N2 C3 -15.6(3) . . . . no
O1 Co1 N3 C5 132.7(3) . . . . no
O1 Co1 N3 C6 -98.5(3) . . . . no
O4 Co1 N3 C5 -54.4(3) . . . . no
O4 Co1 N3 C6 74.5(2) . . . . no
N2 Co1 N3 C5 30.1(3) . . . . no
N2 Co1 N3 C6 158.9(2) . . . . no
N7 Co1 N3 C5 -142.7(3) . . . . no
N7 Co1 N3 C6 -13.9(3) . . . . no
O1 Co1 N7 C7 70.5(2) . . . . no
O1 Co1 N7 C8 -59.2(3) . . . . no
O4 Co1 N7 C7 -102.4(2) . . . . no
O4 Co1 N7 C8 127.9(3) . . . . no
N1 Co1 N7 C7 156.6(2) . . . . no
N1 Co1 N7 C8 26.9(3) . . . . no
N3 Co1 N7 C7 -16.5(2) . . . . no
N3 Co1 N7 C8 -146.2(3) . . . . no
Co1 O1 N5 O2 178.9(3) . . . . no
Co1 O1 N5 O3 7.6(6) . . . . no
Co1 O4 N4 O5 -170.4(3) . . . . no
Co1 O4 N4 O6 10.5(6) . . . . no
Co1 N1 C1 C2 -5.7(4) . . . . no
Co1 N1 C1 C11 174.4(3) . . . . no
C10 N1 C1 C2 -178.5(3) . . . . no
C10 N1 C1 C11 1.6(5) . . . . no
Co1 N1 C10 C9 29.7(4) . . . . no
C1 N1 C10 C9 -158.3(3) . . . . no
Co1 N2 C2 C1 -8.9(4) . . . . no
Co1 N2 C2 C12 169.1(3) . . . . no
C3 N2 C2 C1 -176.7(3) . . . . no
C3 N2 C2 C12 1.2(6) . . . . no
Co1 N2 C3 C4 29.8(5) . . . . no
C2 N2 C3 C4 -163.9(4) . . . . no
Co1 N3 C5 C4 -59.1(4) . . . . no
C6 N3 C5 C4 173.7(3) . . . . no
Co1 N3 C6 C7 40.9(3) . . . . no
C5 N3 C6 C7 173.1(3) . . . . no
Co1 N7 C7 C6 43.1(3) . . . . no
C8 N7 C7 C6 176.0(3) . . . . no
Co1 N7 C8 C9 -55.9(4) . . . . no
C7 N7 C8 C9 176.4(3) . . . . no
N1 C1 C2 N2 9.8(5) . . . . no
N1 C1 C2 C12 -168.2(4) . . . . no
C11 C1 C2 N2 -170.3(3) . . . . no
C11 C1 C2 C12 11.7(5) . . . . no
N2 C3 C4 C5 -56.5(5) . . . . no
C3 C4 C5 N3 72.7(4) . . . . no
N3 C6 C7 N7 -54.8(4) . . . . no
N7 C8 C9 C10 72.6(4) . . . . no
C8 C9 C10 N1 -57.9(5) . . . . no



_vrf_PLAT601_17008               
;
RESPONSE: Solvent THF partically occupied in 
the void channel along the c-axis and can't be 
resolved. Platon SQUEEZE was implemented.
;
####################################################################### 
# 
# 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_16107
_database_code_depnum_ccdc_archive 'CCDC 1823666'
_audit_update_record             
;
2018-02-12 deposited with the CCDC.
2018-05-23 downloaded from the CCDC.
;
_audit_creation_date             2016-11-21
_audit_creation_method           CRYSTALS_ver_14.61_build_00000

_oxford_structure_analysis_title 'mo_16107_0m in P2(1)/c'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_cell_length_a                   9.9394(4)
_cell_length_b                   9.5494(4)
_cell_length_c                   21.4604(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.9342(13)
_cell_angle_gamma                90
_cell_volume                     2036.65(15)

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

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_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Co 0.3494 0.9721 12.2841 4.2791 7.3409 0.2784 4.0034 13.5359 2.3488 71.1692
1.0118 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C14 H27 Br3 Co1 N5 
# Dc =      1.84 Fooo =   1112.00 Mu =     67.34 M =    564.05
# Found Formula = C14 H27 Br3 Co1 N5 
# Dc =      1.84 FOOO =   1112.00 Mu =     67.34 M =    564.05

_chemical_formula_sum            'C14 H27 Br3 Co1 N5'
_chemical_formula_moiety         'C14 H27 Br3 Co1 N5'
_chemical_compound_source        ?
_chemical_formula_weight         564.05


_cell_measurement_reflns_used    9650
_cell_measurement_theta_min      2
_cell_measurement_theta_max      30
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.200

_exptl_crystal_density_diffrn    1.839
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1112
_exptl_absorpt_coefficient_mu    6.734

# Sheldrick geometric approximatio 0.26 0.26 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.26
_exptl_absorpt_correction_T_max  0.26
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            18629
_reflns_number_total             5149
_diffrn_reflns_av_R_equivalents  0.044
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 5149 
# Theoretical number of reflections is about 11828 


_diffrn_reflns_theta_min         1.898
_diffrn_reflns_theta_max         29.951
_diffrn_measured_fraction_theta_max 0.871

_diffrn_reflns_theta_full        25.159
_diffrn_measured_fraction_theta_full 0.972


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_reflns_limit_h_min              -12
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              30

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.76
_refine_diff_density_max         1.09


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         5136
_refine_ls_number_restraints     8
_refine_ls_number_parameters     214
_oxford_refine_ls_R_factor_ref   0.0341
_refine_ls_wR_factor_ref         0.0616
_refine_ls_goodness_of_fit_ref   1.0003
_refine_ls_shift/su_max          0.0009238
_refine_ls_shift/su_mean         0.0000409


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        5136
_refine_ls_R_factor_all          0.0341
_refine_ls_wR_factor_all         0.0616

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4217
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_gt          0.0584

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.02P)² + 1.99P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Br1 Br 0.87309(2) 0.03627(2) 0.367588(10) 0.0166 1.0000 Uani . . . . . .
Br2 Br 0.89355(3) 0.53746(2) 0.384372(12) 0.0231 1.0000 Uani . . . . . .
Br3 Br 0.70502(2) 0.05281(3) 0.182488(11) 0.0203 1.0000 Uani . . . . . .
Co1 Co 0.88611(3) 0.28695(3) 0.373807(13) 0.0136 1.0000 Uani D . . . . .
N1 N 0.93888(19) 0.2563(2) 0.45965(9) 0.0165 1.0000 Uani . . . . . .
N2 N 0.70994(19) 0.2989(2) 0.40922(9) 0.0174 1.0000 Uani . . . . . .
N3 N 0.8261(2) 0.2948(2) 0.28593(9) 0.0178 1.0000 Uani D . . . . .
N4 N 1.0695(2) 0.2941(2) 0.33991(9) 0.0184 1.0000 Uani D . . . . .
N5 N 0.4617(3) 0.0165(3) 0.40171(16) 0.0554 1.0000 Uani . . . . . .
C1 C 0.8396(2) 0.2487(2) 0.49760(11) 0.0175 1.0000 Uani . . . . . .
C2 C 0.7080(2) 0.2857(2) 0.46878(11) 0.0191 1.0000 Uani . . . . . .
C3 C 0.5862(2) 0.3432(3) 0.37547(11) 0.0245 1.0000 Uani . . . . . .
C4 C 0.5853(3) 0.3080(3) 0.30645(11) 0.0255 1.0000 Uani . . . . . .
C5 C 0.7005(3) 0.3718(3) 0.27105(11) 0.0246 1.0000 Uani D . . . . .
C6 C 0.9399(3) 0.3370(3) 0.24672(11) 0.0233 1.0000 Uani D . . . . .
C7 C 1.0633(3) 0.2631(3) 0.27232(11) 0.0227 1.0000 Uani D . . . . .
C8 C 1.1777(2) 0.2158(3) 0.37292(11) 0.0222 1.0000 Uani D . . . . .
C9 C 1.1875(2) 0.2639(3) 0.44034(12) 0.0253 1.0000 Uani . . . . . .
C10 C 1.0746(2) 0.2128(3) 0.48114(11) 0.0215 1.0000 Uani . . . . . .
C11 C 0.8455(3) 0.2009(3) 0.56364(11) 0.0242 1.0000 Uani . . . . . .
C12 C 0.5875(3) 0.3074(3) 0.50865(12) 0.0286 1.0000 Uani . . . . . .
C13 C 0.5200(3) -0.0695(3) 0.37705(15) 0.0370 1.0000 Uani . . . . . .
C14 C 0.5905(3) -0.1811(4) 0.34542(15) 0.0399 1.0000 Uani . . . . . .
H1 H 0.8099(19) 0.2089(19) 0.2758(9) 0.0500 1.0000 Uiso D . . . . .
H2 H 1.093(2) 0.3833(19) 0.3417(9) 0.0500 1.0000 Uiso D . . . . .
H31 H 0.5781 0.4419 0.3795 0.0311 1.0000 Uiso R . . . . .
H32 H 0.5111 0.2991 0.3940 0.0311 1.0000 Uiso R . . . . .
H41 H 0.5920 0.2092 0.3026 0.0310 1.0000 Uiso R . . . . .
H42 H 0.5031 0.3389 0.2880 0.0310 1.0000 Uiso R . . . . .
H51 H 0.7110 0.4666 0.2836 0.0297 1.0000 Uiso R . . . . .
H52 H 0.6820 0.3681 0.2275 0.0297 1.0000 Uiso R . . . . .
H61 H 0.9530 0.4354 0.2494 0.0286 1.0000 Uiso R . . . . .
H62 H 0.9232 0.3115 0.2045 0.0286 1.0000 Uiso R . . . . .
H71 H 1.1423 0.2944 0.2523 0.0285 1.0000 Uiso R . . . . .
H72 H 1.0536 0.1650 0.2664 0.0285 1.0000 Uiso R . . . . .
H81 H 1.2609 0.2302 0.3527 0.0279 1.0000 Uiso R . . . . .
H82 H 1.1561 0.1189 0.3723 0.0279 1.0000 Uiso R . . . . .
H91 H 1.2708 0.2323 0.4576 0.0313 1.0000 Uiso R . . . . .
H92 H 1.1856 0.3633 0.4405 0.0313 1.0000 Uiso R . . . . .
H101 H 1.0889 0.2466 0.5224 0.0266 1.0000 Uiso R . . . . .
H102 H 1.0773 0.1134 0.4813 0.0266 1.0000 Uiso R . . . . .
H111 H 0.9156 0.1341 0.5686 0.0293 1.0000 Uiso R . . . . .
H112 H 0.7622 0.1594 0.5744 0.0293 1.0000 Uiso R . . . . .
H113 H 0.8629 0.2789 0.5900 0.0293 1.0000 Uiso R . . . . .
H121 H 0.5278 0.3727 0.4895 0.0346 1.0000 Uiso R . . . . .
H122 H 0.6164 0.3423 0.5481 0.0346 1.0000 Uiso R . . . . .
H123 H 0.5425 0.2206 0.5141 0.0346 1.0000 Uiso R . . . . .
H141 H 0.6802 -0.1529 0.3372 0.0475 1.0000 Uiso R . . . . .
H142 H 0.5920 -0.2614 0.3715 0.0475 1.0000 Uiso R . . . . .
H143 H 0.5453 -0.2029 0.3073 0.0475 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.072111(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 . Co1 . 2.4009(4) yes
Br2 . Co1 . 2.4039(4) yes
Co1 . N1 . 1.9295(19) yes
Co1 . N2 . 1.9235(19) yes
Co1 . N3 . 1.9700(19) yes
Co1 . N4 . 1.975(2) yes
N1 . C1 . 1.292(3) yes
N1 . C10 . 1.478(3) yes
N2 . C2 . 1.285(3) yes
N2 . C3 . 1.479(3) yes
N3 . C5 . 1.479(3) yes
N3 . C6 . 1.477(3) yes
N3 . H1 . 0.862(17) no
N4 . C7 . 1.481(3) yes
N4 . C8 . 1.481(3) yes
N4 . H2 . 0.882(18) no
N5 . C13 . 1.140(4) yes
C1 . C2 . 1.481(3) yes
C1 . C11 . 1.489(3) yes
C2 . C12 . 1.497(3) yes
C3 . C4 . 1.519(3) yes
C3 . H31 . 0.950 no
C3 . H32 . 0.950 no
C4 . C5 . 1.512(4) yes
C4 . H41 . 0.950 no
C4 . H42 . 0.950 no
C5 . H51 . 0.950 no
C5 . H52 . 0.950 no
C6 . C7 . 1.510(4) yes
C6 . H61 . 0.950 no
C6 . H62 . 0.950 no
C7 . H71 . 0.950 no
C7 . H72 . 0.950 no
C8 . C9 . 1.519(3) yes
C8 . H81 . 0.950 no
C8 . H82 . 0.950 no
C9 . C10 . 1.515(3) yes
C9 . H91 . 0.950 no
C9 . H92 . 0.950 no
C10 . H101 . 0.950 no
C10 . H102 . 0.950 no
C11 . H111 . 0.950 no
C11 . H112 . 0.950 no
C11 . H113 . 0.950 no
C12 . H121 . 0.950 no
C12 . H122 . 0.950 no
C12 . H123 . 0.950 no
C13 . C14 . 1.451(5) yes
C14 . H141 . 0.950 no
C14 . H142 . 0.950 no
C14 . H143 . 0.950 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Br2 . Co1 . Br1 . 177.394(16) yes
Br2 . Co1 . N1 . 93.07(6) yes
Br1 . Co1 . N1 . 85.14(6) yes
Br2 . Co1 . N2 . 86.01(6) yes
Br1 . Co1 . N2 . 91.87(6) yes
N1 . Co1 . N2 . 82.35(8) yes
Br2 . Co1 . N3 . 93.50(6) yes
Br1 . Co1 . N3 . 88.24(6) yes
N1 . Co1 . N3 . 173.23(8) yes
N2 . Co1 . N3 . 96.47(8) yes
Br2 . Co1 . N4 . 88.47(6) yes
Br1 . Co1 . N4 . 93.62(6) yes
N1 . Co1 . N4 . 96.82(8) yes
N2 . Co1 . N4 . 174.36(9) yes
N3 . Co1 . N4 . 85.01(8) yes
Co1 . N1 . C1 . 114.33(16) yes
Co1 . N1 . C10 . 124.97(15) yes
C1 . N1 . C10 . 119.4(2) yes
Co1 . N2 . C2 . 114.56(16) yes
Co1 . N2 . C3 . 125.36(15) yes
C2 . N2 . C3 . 119.3(2) yes
Co1 . N3 . C5 . 117.82(15) yes
Co1 . N3 . C6 . 109.44(15) yes
C5 . N3 . C6 . 113.12(19) yes
Co1 . N3 . H1 . 104.9(13) no
C5 . N3 . H1 . 105.4(13) no
C6 . N3 . H1 . 104.9(13) no
Co1 . N4 . C7 . 109.24(15) yes
Co1 . N4 . C8 . 118.29(15) yes
C7 . N4 . C8 . 112.75(19) yes
Co1 . N4 . H2 . 104.9(13) no
C7 . N4 . H2 . 104.0(13) no
C8 . N4 . H2 . 106.3(13) no
N1 . C1 . C2 . 113.7(2) yes
N1 . C1 . C11 . 126.8(2) yes
C2 . C1 . C11 . 119.4(2) yes
C1 . C2 . N2 . 114.3(2) yes
C1 . C2 . C12 . 120.2(2) yes
N2 . C2 . C12 . 125.5(2) yes
N2 . C3 . C4 . 113.9(2) yes
N2 . C3 . H31 . 108.1 no
C4 . C3 . H31 . 108.0 no
N2 . C3 . H32 . 108.7 no
C4 . C3 . H32 . 108.6 no
H31 . C3 . H32 . 109.5 no
C3 . C4 . C5 . 114.1(2) yes
C3 . C4 . H41 . 107.8 no
C5 . C4 . H41 . 107.6 no
C3 . C4 . H42 . 109.2 no
C5 . C4 . H42 . 108.6 no
H41 . C4 . H42 . 109.5 no
C4 . C5 . N3 . 109.5(2) yes
C4 . C5 . H51 . 108.7 no
N3 . C5 . H51 . 108.9 no
C4 . C5 . H52 . 110.1 no
N3 . C5 . H52 . 110.1 no
H51 . C5 . H52 . 109.5 no
N3 . C6 . C7 . 106.83(19) yes
N3 . C6 . H61 . 109.9 no
C7 . C6 . H61 . 109.3 no
N3 . C6 . H62 . 110.5 no
C7 . C6 . H62 . 110.8 no
H61 . C6 . H62 . 109.5 no
C6 . C7 . N4 . 106.50(19) yes
C6 . C7 . H71 . 111.2 no
N4 . C7 . H71 . 110.9 no
C6 . C7 . H72 . 109.4 no
N4 . C7 . H72 . 109.3 no
H71 . C7 . H72 . 109.5 no
N4 . C8 . C9 . 109.76(19) yes
N4 . C8 . H81 . 109.8 no
C9 . C8 . H81 . 110.5 no
N4 . C8 . H82 . 108.8 no
C9 . C8 . H82 . 108.6 no
H81 . C8 . H82 . 109.5 no
C8 . C9 . C10 . 114.6(2) yes
C8 . C9 . H91 . 108.5 no
C10 . C9 . H91 . 108.7 no
C8 . C9 . H92 . 107.7 no
C10 . C9 . H92 . 107.8 no
H91 . C9 . H92 . 109.5 no
C9 . C10 . N1 . 114.2(2) yes
C9 . C10 . H101 . 109.2 no
N1 . C10 . H101 . 108.5 no
C9 . C10 . H102 . 107.6 no
N1 . C10 . H102 . 107.8 no
H101 . C10 . H102 . 109.5 no
C1 . C11 . H111 . 109.3 no
C1 . C11 . H112 . 109.8 no
H111 . C11 . H112 . 109.5 no
C1 . C11 . H113 . 109.3 no
H111 . C11 . H113 . 109.5 no
H112 . C11 . H113 . 109.5 no
C2 . C12 . H121 . 110.0 no
C2 . C12 . H122 . 109.0 no
H121 . C12 . H122 . 109.5 no
C2 . C12 . H123 . 109.4 no
H121 . C12 . H123 . 109.5 no
H122 . C12 . H123 . 109.5 no
N5 . C13 . C14 . 178.4(3) yes
C13 . C14 . H141 . 110.0 no
C13 . C14 . H142 . 108.7 no
H141 . C14 . H142 . 109.5 no
C13 . C14 . H143 . 109.8 no
H141 . C14 . H143 . 109.5 no
H142 . C14 . H143 . 109.5 no

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
Br1 Co1 N1 C1 -88.29(15) . . . . no
Br1 Co1 N1 C10 78.25(19) . . . . no
Br2 Co1 N1 C1 89.82(15) . . . . no
Br2 Co1 N1 C10 -103.65(19) . . . . no
N2 Co1 N1 C1 4.26(16) . . . . no
N2 Co1 N1 C10 170.8(2) . . . . no
N4 Co1 N1 C1 178.63(16) . . . . no
N4 Co1 N1 C10 -14.8(2) . . . . no
Br1 Co1 N2 C2 86.36(15) . . . . no
Br1 Co1 N2 C3 -103.88(19) . . . . no
Br2 Co1 N2 C2 -92.12(15) . . . . no
Br2 Co1 N2 C3 77.64(19) . . . . no
N1 Co1 N2 C2 1.51(16) . . . . no
N1 Co1 N2 C3 171.3(2) . . . . no
N3 Co1 N2 C2 174.81(16) . . . . no
N3 Co1 N2 C3 -15.4(2) . . . . no
Br1 Co1 N3 C5 120.85(17) . . . . no
Br1 Co1 N3 C6 -108.03(15) . . . . no
Br2 Co1 N3 C5 -57.20(17) . . . . no
Br2 Co1 N3 C6 73.92(15) . . . . no
N2 Co1 N3 C5 29.17(18) . . . . no
N2 Co1 N3 C6 160.30(16) . . . . no
N4 Co1 N3 C5 -145.35(18) . . . . no
N4 Co1 N3 C6 -14.23(16) . . . . no
Br1 Co1 N4 C7 72.96(15) . . . . no
Br1 Co1 N4 C8 -57.77(17) . . . . no
Br2 Co1 N4 C7 -108.60(15) . . . . no
Br2 Co1 N4 C8 120.68(17) . . . . no
N1 Co1 N4 C7 158.50(16) . . . . no
N1 Co1 N4 C8 27.77(18) . . . . no
N3 Co1 N4 C7 -14.96(16) . . . . no
N3 Co1 N4 C8 -145.69(18) . . . . no
Co1 N1 C1 C2 -8.5(2) . . . . no
Co1 N1 C1 C11 168.17(19) . . . . no
C10 N1 C1 C2 -175.84(19) . . . . no
C10 N1 C1 C11 0.8(3) . . . . no
Co1 N1 C10 C9 30.7(3) . . . . no
C1 N1 C10 C9 -163.4(2) . . . . no
Co1 N2 C2 C1 -6.3(2) . . . . no
Co1 N2 C2 C12 172.42(18) . . . . no
C3 N2 C2 C1 -176.71(19) . . . . no
C3 N2 C2 C12 2.0(3) . . . . no
Co1 N2 C3 C4 30.5(3) . . . . no
C2 N2 C3 C4 -160.2(2) . . . . no
Co1 N3 C5 C4 -58.8(2) . . . . no
C6 N3 C5 C4 171.8(2) . . . . no
Co1 N3 C6 C7 39.7(2) . . . . no
C5 N3 C6 C7 173.3(2) . . . . no
Co1 N4 C7 C6 40.1(2) . . . . no
C8 N4 C7 C6 173.8(2) . . . . no
Co1 N4 C8 C9 -56.7(2) . . . . no
C7 N4 C8 C9 174.1(2) . . . . no
N1 C1 C2 N2 9.9(3) . . . . no
N1 C1 C2 C12 -168.9(2) . . . . no
C11 C1 C2 N2 -167.1(2) . . . . no
C11 C1 C2 C12 14.2(3) . . . . no
N2 C3 C4 C5 -58.6(3) . . . . no
C3 C4 C5 N3 74.6(3) . . . . no
N3 C6 C7 N4 -51.9(3) . . . . no
N4 C8 C9 C10 73.7(3) . . . . no
C8 C9 C10 N1 -59.0(3) . . . . no


