# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_Py-NNN-CoBr2
_audit_block_doi                 10.5517/ccdc.csd.cc1p8hr6
_database_code_depnum_ccdc_archive 'CCDC 1557308'
_audit_update_record             
;
2017-06-20 deposited with the CCDC.
2017-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H23 Br2 Co N3 O2'
_chemical_formula_sum            'C15 H23 Br2 Co N3 O2'
_chemical_formula_weight         496.11

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'
N N 0.0061 0.0033 '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'
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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.2514(4)
_cell_length_b                   14.6308(6)
_cell_length_c                   12.6552(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.105(4)
_cell_angle_gamma                90
_cell_volume                     1896.84(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2949
_cell_measurement_theta_min      3.8020
_cell_measurement_theta_max      27.7520

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.737
_exptl_crystal_F_000             988
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    5.129
_shelx_estimated_absorpt_T_min   0.184
_shelx_estimated_absorpt_T_max   0.427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.184
_exptl_absorpt_correction_T_max  0.427
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1640
_diffrn_reflns_number            8187
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.953
_diffrn_reflns_theta_max         28.888
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.858
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4280
_reflns_number_gt                3104
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0326P)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_number_reflns         4280
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.001
_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
Br1 Br 0.94000(5) 0.19195(3) 0.59269(3) 0.04429(15) Uani 1 1 d . . . . .
Co3 Co 0.90952(6) 0.20885(4) 0.40534(4) 0.03830(18) Uani 1 1 d . . . . .
N1 N 1.1157(3) 0.2948(2) 0.3646(3) 0.0348(8) Uani 1 1 d . . . . .
N2 N 0.9943(3) 0.1406(2) 0.2867(2) 0.0317(8) Uani 1 1 d . . . . .
N3 N 0.7726(3) 0.0812(2) 0.3799(2) 0.0332(8) Uani 1 1 d . . . . .
C4 C 1.0073(4) 0.0056(3) 0.1841(3) 0.0475(12) Uani 1 1 d . . . . .
H4 H 0.9830 -0.0549 0.1720 0.057 Uiso 1 1 calc R U . . .
C1 C 1.0768(4) 0.1834(3) 0.2227(3) 0.0351(10) Uani 1 1 d . . . . .
O6 O 0.4963(3) 0.1052(2) 0.4127(2) 0.0536(8) Uani 1 1 d . . . . .
C10 C 1.1185(5) 0.3943(3) 0.3866(3) 0.0474(12) Uani 1 1 d . . . . .
H10A H 1.0351 0.4212 0.3656 0.057 Uiso 1 1 calc R U . . .
H10B H 1.1855 0.4231 0.3459 0.057 Uiso 1 1 calc R U . . .
C5 C 0.9601(4) 0.0539(3) 0.2690(3) 0.0342(10) Uani 1 1 d . . . . .
C15 C 0.7060(4) 0.0447(3) 0.4733(3) 0.0420(11) Uani 1 1 d . . . . .
H15A H 0.7668 0.0434 0.5339 0.050 Uiso 1 1 calc R U . . .
H15B H 0.6770 -0.0173 0.4591 0.050 Uiso 1 1 calc R U . . .
C12 C 0.6734(4) 0.0897(3) 0.2915(3) 0.0429(11) Uani 1 1 d . . . . .
H12A H 0.6460 0.0290 0.2690 0.052 Uiso 1 1 calc R U . . .
H12B H 0.7131 0.1192 0.2320 0.052 Uiso 1 1 calc R U . . .
C2 C 1.1269(4) 0.1392(3) 0.1367(3) 0.0447(11) Uani 1 1 d . . . . .
H2 H 1.1834 0.1690 0.0923 0.054 Uiso 1 1 calc R U . . .
C13 C 0.5557(5) 0.1434(3) 0.3213(4) 0.0521(12) Uani 1 1 d . . . . .
H13A H 0.5812 0.2061 0.3360 0.062 Uiso 1 1 calc R U . . .
H13B H 0.4926 0.1438 0.2623 0.062 Uiso 1 1 calc R U . . .
C14 C 0.5910(5) 0.1035(3) 0.4976(3) 0.0497(12) Uani 1 1 d . . . . .
H14A H 0.5510 0.0804 0.5606 0.060 Uiso 1 1 calc R U . . .
H14B H 0.6208 0.1653 0.5122 0.060 Uiso 1 1 calc R U . . .
C3 C 1.0907(4) 0.0494(3) 0.1185(3) 0.0505(13) Uani 1 1 d . . . . .
H3 H 1.1232 0.0182 0.0610 0.061 Uiso 1 1 calc R U . . .
C9 C 1.1464(5) 0.4108(3) 0.5026(4) 0.0571(13) Uani 1 1 d . . . . .
H9A H 1.1459 0.4760 0.5164 0.069 Uiso 1 1 calc R U . . .
H9B H 1.0782 0.3830 0.5429 0.069 Uiso 1 1 calc R U . . .
C7 C 1.2416(5) 0.2538(4) 0.4042(4) 0.0506(12) Uani 1 1 d . . . . .
H7A H 1.3119 0.2760 0.3618 0.061 Uiso 1 1 calc R U . . .
H7B H 1.2374 0.1879 0.3965 0.061 Uiso 1 1 calc R U . . .
C8 C 1.2706(5) 0.2774(4) 0.5186(4) 0.0618(14) Uani 1 1 d . . . . .
H8A H 1.2056 0.2491 0.5618 0.074 Uiso 1 1 calc R U . . .
H8B H 1.3552 0.2527 0.5402 0.074 Uiso 1 1 calc R U . . .
C11 C 0.8727(4) 0.0145(3) 0.3499(3) 0.0402(10) Uani 1 1 d . . . . .
H11A H 0.8303 -0.0399 0.3214 0.048 Uiso 1 1 calc R U . . .
H11B H 0.9246 -0.0031 0.4122 0.048 Uiso 1 1 calc R U . . .
C6 C 1.1035(4) 0.2814(3) 0.2490(3) 0.0407(11) Uani 1 1 d . . . . .
H6B H 1.1837 0.3004 0.2170 0.049 Uiso 1 1 calc R U . . .
H6A H 1.0331 0.3191 0.2201 0.049 Uiso 1 1 calc R U . . .
O1 O 1.2705(3) 0.3734(3) 0.5361(3) 0.0656(10) Uani 1 1 d . . . . .
Br2 Br 0.77967(5) 0.33848(3) 0.35336(4) 0.05297(17) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Co3 2.3928(7) . ?
Co3 N2 2.026(3) . ?
Co3 N3 2.351(3) . ?
Co3 Br2 2.3953(7) . ?
Co3 N1 2.529(3) . ?
N1 C6 1.476(5) . ?
N1 C10 1.483(5) . ?
N1 C7 1.493(5) . ?
N2 C5 1.332(5) . ?
N2 C1 1.347(5) . ?
N3 C11 1.475(5) . ?
N3 C15 1.486(5) . ?
N3 C12 1.490(5) . ?
C4 C3 1.372(6) . ?
C4 C5 1.388(5) . ?
C4 H4 0.9300 . ?
C1 C2 1.382(5) . ?
C1 C6 1.496(5) . ?
O6 C14 1.422(5) . ?
O6 C13 1.440(5) . ?
C10 C9 1.504(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C5 C11 1.501(5) . ?
C15 C14 1.500(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C12 C13 1.499(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C2 C3 1.383(6) . ?
C2 H2 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C3 H3 0.9300 . ?
C9 O1 1.436(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C7 C8 1.506(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O1 1.422(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6A 0.9700 . ?

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
N2 Co3 N3 77.11(12) . . ?
N2 Co3 Br1 129.75(9) . . ?
N3 Co3 Br1 96.26(8) . . ?
N2 Co3 Br2 115.86(9) . . ?
N3 Co3 Br2 105.57(8) . . ?
Br1 Co3 Br2 113.89(3) . . ?
N2 Co3 N1 73.11(12) . . ?
N3 Co3 N1 150.03(11) . . ?
Br1 Co3 N1 100.00(8) . . ?
Br2 Co3 N1 90.61(8) . . ?
C6 N1 C10 108.4(3) . . ?
C6 N1 C7 108.7(3) . . ?
C10 N1 C7 108.7(3) . . ?
C6 N1 Co3 95.5(2) . . ?
C10 N1 Co3 117.4(3) . . ?
C7 N1 Co3 116.8(3) . . ?
C5 N2 C1 120.6(3) . . ?
C5 N2 Co3 118.5(3) . . ?
C1 N2 Co3 120.8(3) . . ?
C11 N3 C15 108.1(3) . . ?
C11 N3 C12 108.8(3) . . ?
C15 N3 C12 107.9(3) . . ?
C11 N3 Co3 98.3(2) . . ?
C15 N3 Co3 117.8(2) . . ?
C12 N3 Co3 115.1(2) . . ?
C3 C4 C5 118.2(4) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
N2 C1 C2 121.1(4) . . ?
N2 C1 C6 115.2(3) . . ?
C2 C1 C6 123.6(4) . . ?
C14 O6 C13 108.5(3) . . ?
N1 C10 C9 110.0(4) . . ?
N1 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
N1 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
N2 C5 C4 121.2(4) . . ?
N2 C5 C11 114.3(3) . . ?
C4 C5 C11 124.5(4) . . ?
N3 C15 C14 110.2(3) . . ?
N3 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
N3 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
N3 C12 C13 112.8(4) . . ?
N3 C12 H12A 109.0 . . ?
C13 C12 H12A 109.0 . . ?
N3 C12 H12B 109.0 . . ?
C13 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C1 C2 C3 118.1(4) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
O6 C13 C12 111.5(4) . . ?
O6 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
O6 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
O6 C14 C15 112.0(4) . . ?
O6 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
O6 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
O1 C9 C10 111.2(4) . . ?
O1 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
O1 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
N1 C7 C8 111.6(4) . . ?
N1 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
O1 C8 C7 112.0(4) . . ?
O1 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
O1 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N3 C11 C5 111.1(3) . . ?
N3 C11 H11A 109.4 . . ?
C5 C11 H11A 109.4 . . ?
N3 C11 H11B 109.4 . . ?
C5 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N1 C6 C1 110.8(3) . . ?
N1 C6 H6B 109.5 . . ?
C1 C6 H6B 109.5 . . ?
N1 C6 H6A 109.5 . . ?
C1 C6 H6A 109.5 . . ?
H6B C6 H6A 108.1 . . ?
C8 O1 C9 109.6(4) . . ?

_refine_diff_density_max         0.723
_refine_diff_density_min         -0.851
_refine_diff_density_rms         0.106

