# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_anke35_22
_database_code_depnum_ccdc_archive 'CCDC 1060544'
_audit_update_record             
;
2015-04-20 deposited with the CCDC.
2015-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H21 Br Co N O4'
_chemical_formula_sum            'C16 H21 Br Co N O4'
_chemical_formula_weight         430.18

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           8
_space_group_name_H-M_alt        'C m'
_space_group_name_Hall           'C -2y'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'

_cell_length_a                   8.2934(10)
_cell_length_b                   13.814(2)
_cell_length_c                   7.8377(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.388(15)
_cell_angle_gamma                90
_cell_volume                     897.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2521
_cell_measurement_theta_min      3.7920
_cell_measurement_theta_max      25.4260

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    3.201
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.86669
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
' 90 images, ΔΦ 3.3° '
' 55 images, ΔΦ 3.3° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7742
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.867
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             1667
_reflns_number_gt                1622
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.973
_reflns_Friedel_fraction_max     0.945
_reflns_Friedel_fraction_full    0.959

_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.
;

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;



_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0699P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 774 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.028(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1667
_refine_ls_number_parameters     120
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0914
_refine_ls_wR_factor_gt          0.0906
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 1.01202(10) 0.0000 0.00543(10) 0.0217(3) Uani 1 2 d S T P . .
O2 O 1.1101(5) 0.0913(3) 0.1553(5) 0.0274(8) Uani 1 1 d . . . . .
C3 C 1.1201(7) 0.1831(4) 0.1242(7) 0.0265(11) Uani 1 1 d . . . . .
C4 C 1.0546(8) 0.2277(4) -0.0216(8) 0.0315(12) Uani 1 1 d . . . . .
H4 H 1.0787 0.2942 -0.0384 0.038 Uiso 1 1 calc R U . . .
C5 C 0.9557(6) 0.1816(4) -0.1450(8) 0.0281(12) Uani 1 1 d . . . . .
O6 O 0.9139(5) 0.0931(3) -0.1426(5) 0.0269(8) Uani 1 1 d . . . . .
C7 C 1.2096(8) 0.2385(5) 0.2610(8) 0.0346(13) Uani 1 1 d . . . . .
H7A H 1.1531 0.2329 0.3679 0.052 Uiso 1 1 calc R U . . .
H7B H 1.2155 0.3068 0.2279 0.052 Uiso 1 1 calc R U . . .
H7C H 1.3189 0.2123 0.2771 0.052 Uiso 1 1 calc R U . . .
C8 C 0.8907(9) 0.2377(5) -0.2977(8) 0.0396(15) Uani 1 1 d . . . . .
H8A H 0.9252 0.2066 -0.4025 0.059 Uiso 1 1 calc R U . . .
H8B H 0.9321 0.3041 -0.2922 0.059 Uiso 1 1 calc R U . . .
H8C H 0.7726 0.2388 -0.2978 0.059 Uiso 1 1 calc R U . . .
C9 C 1.2068(10) 0.0000 -0.1223(9) 0.0278(17) Uani 1 2 d S T P . .
H9A H 1.2710 -0.0577 -0.0877 0.033 Uiso 0.5 1 calc R U P . .
H9B H 1.2710 0.0577 -0.0877 0.033 Uiso 0.5 1 calc R U P . .
Br10 Br 1.18099(8) 0.0000 -0.37124(8) 0.0420(3) Uani 1 2 d S T P . .
N11 N 0.8125(8) 0.0000 0.1605(9) 0.0226(13) Uani 1 2 d S T P . .
C12 C 0.6602(9) 0.0000 0.1020(10) 0.0228(15) Uani 1 2 d S T P . .
H12 H 0.6382 0.0000 -0.0180 0.027 Uiso 1 2 calc R U P . .
C13 C 0.5313(13) 0.0000 0.2104(15) 0.037(2) Uani 1 2 d S T P . .
H13 H 0.4233 0.0000 0.1649 0.044 Uiso 1 2 calc R U P . .
C14 C 0.5627(11) 0.0000 0.3861(15) 0.042(2) Uani 1 2 d S T P . .
H14 H 0.4766 0.0000 0.4623 0.051 Uiso 1 2 calc R U P . .
C15 C 0.7194(13) 0.0000 0.4472(12) 0.034(2) Uani 1 2 d S T P . .
H15 H 0.7439 0.0000 0.5667 0.041 Uiso 1 2 calc R U P . .
C16 C 0.8455(11) 0.0000 0.3289(11) 0.0280(18) Uani 1 2 d S T P . .
H16 H 0.9547 0.0000 0.3705 0.034 Uiso 1 2 calc R U P . .


_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 O2 1.885(4) 2 y
Co1 O2 1.885(4) . y
Co1 O6 1.893(4) . y
Co1 O6 1.893(4) 2 y
Co1 C9 1.935(8) . y
Co1 N11 2.094(7) . y
O2 C3 1.295(7) . ?
C3 C4 1.389(8) . ?
C3 C7 1.490(8) . ?
C4 C5 1.396(9) . ?
C4 H4 0.9500 . ?
C5 O6 1.272(7) . ?
C5 C8 1.507(8) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 Br10 1.954(7) . y
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N11 C12 1.326(10) . ?
N11 C16 1.337(11) . ?
C12 C13 1.393(14) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.366(14) . ?
C14 H14 0.9500 . ?
C15 C16 1.426(16) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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
O2 Co1 O2 84.0(2) 2 . y
O2 Co1 O6 179.17(18) 2 . y
O2 Co1 O6 95.23(16) . . y
O2 Co1 O6 95.23(16) 2 2 y
O2 Co1 O6 179.17(18) . 2 y
O6 Co1 O6 85.6(2) . 2 y
O2 Co1 C9 88.6(2) 2 . y
O2 Co1 C9 88.6(2) . . y
O6 Co1 C9 91.7(2) . . y
O6 Co1 C9 91.7(2) 2 . y
O2 Co1 N11 88.22(19) 2 . y
O2 Co1 N11 88.22(19) . . y
O6 Co1 N11 91.48(19) . . y
O6 Co1 N11 91.48(19) 2 . y
C9 Co1 N11 175.7(3) . . y
C3 O2 Co1 124.6(4) . . ?
O2 C3 C4 124.3(5) . . ?
O2 C3 C7 113.7(5) . . ?
C4 C3 C7 122.0(5) . . ?
C3 C4 C5 124.5(5) . . ?
C3 C4 H4 117.8 . . ?
C5 C4 H4 117.8 . . ?
O6 C5 C4 125.6(5) . . ?
O6 C5 C8 114.6(5) . . ?
C4 C5 C8 119.8(6) . . ?
C5 O6 Co1 123.5(3) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Co1 C9 Br10 117.2(4) . . y
Co1 C9 H9A 108.0 . . ?
Br10 C9 H9A 108.0 . . ?
Co1 C9 H9B 108.0 . . ?
Br10 C9 H9B 108.0 . . ?
H9A C9 H9B 107.2 . . ?
C12 N11 C16 119.6(7) . . ?
C12 N11 Co1 124.3(5) . . ?
C16 N11 Co1 116.0(6) . . ?
N11 C12 C13 122.2(7) . . ?
N11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C14 C13 C12 119.2(9) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C15 C14 C13 118.9(10) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 119.0(9) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
N11 C16 C15 121.1(8) . . ?
N11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?

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
O2 Co1 O2 C3 168.6(4) 2 . . . ?
O6 Co1 O2 C3 -11.7(5) . . . . ?
C9 Co1 O2 C3 79.9(5) . . . . ?
N11 Co1 O2 C3 -103.0(5) . . . . ?
Co1 O2 C3 C4 2.5(8) . . . . ?
Co1 O2 C3 C7 -177.6(4) . . . . ?
O2 C3 C4 C5 6.8(10) . . . . ?
C7 C3 C4 C5 -173.0(6) . . . . ?
C3 C4 C5 O6 -1.0(10) . . . . ?
C3 C4 C5 C8 179.7(6) . . . . ?
C4 C5 O6 Co1 -13.1(8) . . . . ?
C8 C5 O6 Co1 166.3(4) . . . . ?
O2 Co1 O6 C5 16.7(5) . . . . ?
O6 Co1 O6 C5 -163.6(4) 2 . . . ?
C9 Co1 O6 C5 -72.0(5) . . . . ?
N11 Co1 O6 C5 105.1(5) . . . . ?
C16 N11 C12 C13 0.000(1) . . . . ?
Co1 N11 C12 C13 180.000(1) . . . . ?
N11 C12 C13 C14 0.000(1) . . . . ?
C12 C13 C14 C15 0.000(1) . . . . ?
C13 C14 C15 C16 0.000(2) . . . . ?
C12 N11 C16 C15 0.000(1) . . . . ?
Co1 N11 C16 C15 180.000(1) . . . . ?
C14 C15 C16 N11 0.000(1) . . . . ?

_refine_diff_density_max         0.628
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.095

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pyridine benzene pentane'
_chemical_properties_physical    Air-sensitive
####################################################################### 
# 
# 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_jedeb19i_pyr
_database_code_depnum_ccdc_archive 'CCDC 1060545'
_audit_update_record             
;
2015-04-20 deposited with the CCDC.
2015-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H21 Cl Co N O4'
_chemical_formula_sum            'C16 H21 Cl Co N O4'
_chemical_formula_weight         385.72

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           8
_space_group_name_H-M_alt        'C m'
_space_group_name_Hall           'C -2y'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'

_cell_length_a                   8.1891(2)
_cell_length_b                   13.7998(3)
_cell_length_c                   7.73787(19)
_cell_angle_alpha                90
_cell_angle_beta                 91.890(2)
_cell_angle_gamma                90
_cell_volume                     873.96(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2860
_cell_measurement_theta_min      2.9430
_cell_measurement_theta_max      25.4130

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.152
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.88449
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '150 images, ΔΦ 1.5° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3636
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.894
_diffrn_reflns_theta_max         25.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             1636
_reflns_number_gt                1585
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.991
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.985

_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.
;

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;

_refine_special_details          Twin
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0408P)²+0.8561P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.50(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1636
_refine_ls_number_parameters     121
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0807
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 1.01396(8) 0.0000 -0.00222(7) 0.0219(2) Uani 1 2 d S T P . .
O2 O 1.1141(4) 0.0921(3) 0.1477(4) 0.0254(9) Uani 1 1 d . . . . .
C3 C 1.1223(6) 0.1823(4) 0.1170(6) 0.0255(11) Uani 1 1 d . . . . .
C4 C 1.0558(6) 0.2275(4) -0.0292(6) 0.0306(11) Uani 1 1 d . . . . .
H4 H 1.0799 0.2941 -0.0453 0.037 Uiso 1 1 calc R U . . .
C5 C 0.9564(6) 0.1821(4) -0.1537(6) 0.0272(12) Uani 1 1 d . . . . .
O6 O 0.9139(4) 0.0927(3) -0.1505(4) 0.0272(10) Uani 1 1 d . . . . .
C7 C 1.2110(7) 0.2395(4) 0.2558(7) 0.0346(12) Uani 1 1 d . . . . .
H7A H 1.1370 0.2529 0.3498 0.052 Uiso 1 1 calc R U . . .
H7B H 1.2491 0.3008 0.2075 0.052 Uiso 1 1 calc R U . . .
H7C H 1.3050 0.2022 0.3007 0.052 Uiso 1 1 calc R U . . .
C8 C 0.8916(7) 0.2375(4) -0.3085(6) 0.0360(12) Uani 1 1 d . . . . .
H8A H 0.9293 0.2068 -0.4142 0.054 Uiso 1 1 calc R U . . .
H8B H 0.9313 0.3044 -0.3025 0.054 Uiso 1 1 calc R U . . .
H8C H 0.7719 0.2373 -0.3098 0.054 Uiso 1 1 calc R U . . .
C9 C 1.2111(9) 0.0000 -0.1385(9) 0.0265(18) Uani 1 2 d S T P . .
H9A H 1.2767 0.0578 -0.1057 0.032 Uiso 0.5 1 calc R U P . .
H9B H 1.2767 -0.0578 -0.1057 0.032 Uiso 0.5 1 calc R U P . .
Cl10 Cl 1.1802(3) 0.0000 -0.3678(3) 0.0478(7) Uani 1 2 d S T P . .
N11 N 0.8129(8) 0.0000 0.1592(8) 0.0242(14) Uani 1 2 d S T P . .
C12 C 0.6571(8) 0.0000 0.1019(9) 0.0266(14) Uani 1 2 d S T P . .
H12 H 0.6342 0.0000 -0.0193 0.032 Uiso 1 2 calc R U P . .
C13 C 0.5288(9) 0.0000 0.2120(10) 0.0337(16) Uani 1 2 d S T P . .
H13 H 0.4194 0.0000 0.1672 0.040 Uiso 1 2 calc R U P . .
C14 C 0.5603(10) 0.0000 0.3879(10) 0.0378(17) Uani 1 2 d S T P . .
H14 H 0.4732 0.0000 0.4660 0.045 Uiso 1 2 calc R U P . .
C15 C 0.7202(9) 0.0000 0.4487(9) 0.0317(16) Uani 1 2 d S T P . .
H15 H 0.7456 0.0000 0.5694 0.038 Uiso 1 2 calc R U P . .
C16 C 0.8435(10) 0.0000 0.3299(9) 0.0249(16) Uani 1 2 d S T P . .
H16 H 0.9540 0.0000 0.3715 0.030 Uiso 1 2 calc R U P . .


_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 O6 1.887(4) . y
Co1 O6 1.887(4) 2 y
Co1 O2 1.889(4) 2 y
Co1 O2 1.889(4) . y
Co1 C9 1.957(7) . y
Co1 N11 2.099(7) . y
O2 C3 1.270(6) . ?
C3 C4 1.387(7) . ?
C3 C7 1.501(7) . ?
C4 C5 1.389(7) . ?
C4 H4 0.9500 . ?
C5 O6 1.283(7) . ?
C5 C8 1.502(7) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 Cl10 1.784(7) . y
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N11 C16 1.336(9) . ?
N11 C12 1.337(9) . ?
C12 C13 1.375(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(11) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(11) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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
O6 Co1 O6 85.3(3) . 2 y
O6 Co1 O2 179.5(2) . 2 y
O6 Co1 O2 95.09(11) 2 2 y
O6 Co1 O2 95.09(11) . . y
O6 Co1 O2 179.6(2) 2 . y
O2 Co1 O2 84.5(2) 2 . y
O6 Co1 C9 91.25(18) . . y
O6 Co1 C9 91.24(18) 2 . y
O2 Co1 C9 88.95(19) 2 . y
O2 Co1 C9 88.95(19) . . y
O6 Co1 N11 91.63(17) . . y
O6 Co1 N11 91.63(17) 2 . y
O2 Co1 N11 88.16(16) 2 . y
O2 Co1 N11 88.16(16) . . y
C9 Co1 N11 176.1(3) . . y
C3 O2 Co1 124.7(3) . . ?
O2 C3 C4 124.9(5) . . ?
O2 C3 C7 114.1(5) . . ?
C4 C3 C7 121.0(5) . . ?
C3 C4 C5 124.6(5) . . ?
C3 C4 H4 117.7 . . ?
C5 C4 H4 117.7 . . ?
O6 C5 C4 125.0(5) . . ?
O6 C5 C8 114.6(5) . . ?
C4 C5 C8 120.5(5) . . ?
C5 O6 Co1 123.4(3) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
Cl10 C9 Co1 116.3(4) . . ?
Cl10 C9 H9A 108.2 . . ?
Co1 C9 H9A 108.2 . . ?
Cl10 C9 H9B 108.2 . . ?
Co1 C9 H9B 108.2 . . ?
H9A C9 H9B 107.4 . . ?
C16 N11 C12 118.3(6) . . ?
C16 N11 Co1 117.6(5) . . ?
C12 N11 Co1 124.1(5) . . ?
N11 C12 C13 122.3(6) . . ?
N11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C14 C13 C12 119.4(7) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 118.8(7) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C14 C15 C16 118.6(7) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
N11 C16 C15 122.5(7) . . ?
N11 C16 H16 118.7 . . ?
C15 C16 H16 118.7 . . ?

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
O6 Co1 O2 C3 -10.9(4) . . . . ?
O2 Co1 O2 C3 169.3(3) 2 . . . ?
C9 Co1 O2 C3 80.2(4) . . . . ?
N11 Co1 O2 C3 -102.4(4) . . . . ?
Co1 O2 C3 C4 1.6(7) . . . . ?
Co1 O2 C3 C7 -179.0(3) . . . . ?
O2 C3 C4 C5 7.1(7) . . . . ?
C7 C3 C4 C5 -172.3(5) . . . . ?
C3 C4 C5 O6 -0.4(8) . . . . ?
C3 C4 C5 C8 -179.5(5) . . . . ?
C4 C5 O6 Co1 -13.6(7) . . . . ?
C8 C5 O6 Co1 165.6(4) . . . . ?
O6 Co1 O6 C5 -163.6(3) 2 . . . ?
O2 Co1 O6 C5 16.6(4) . . . . ?
C9 Co1 O6 C5 -72.4(4) . . . . ?
N11 Co1 O6 C5 104.9(4) . . . . ?
C16 N11 C12 C13 0.000(1) . . . . ?
Co1 N11 C12 C13 180.000(0) . . . . ?
N11 C12 C13 C14 0.000(1) . . . . ?
C12 C13 C14 C15 0.000(1) . . . . ?
C13 C14 C15 C16 0.000(1) . . . . ?
C12 N11 C16 C15 0.000(1) . . . . ?
Co1 N11 C16 C15 180.000(1) . . . . ?
C14 C15 C16 N11 0.000(1) . . . . ?

_refine_diff_density_max         0.678
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.067

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pyridine benzene pentane'
_chemical_properties_physical    Air-sensitive
