# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1958070'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;Department of Chemistry, University of Zurich
Switzerland
;
_audit_update_record             
;
2019-10-08 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

_audit_creation_date             2018-10-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H46 N4 O6 P2'
_chemical_formula_sum            'C36 H46 N4 O6 P2'
_chemical_formula_weight         692.71
_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'
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'
P P 0.1023 0.0942 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4370(2)
_cell_length_b                   10.4908(3)
_cell_length_c                   18.5143(4)
_cell_angle_alpha                96.9776(19)
_cell_angle_beta                 99.2858(19)
_cell_angle_gamma                104.161(2)
_cell_volume                     1728.96(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    19683
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      32.6700
_cell_measurement_theta_min      2.5450
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.924
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.1343
5 -5 -1 0.2038
5 -1 4 0.1614
-4 5 -1 0.1899
-3 0 5 0.0960
0 -1 0 0.1393
-2 5 -3 0.1938
-2 0 5 0.0886
0 -5 -3 0.1462
5 0 -1 0.1446
0 0 1 0.1093

_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.24

_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            34712
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.607
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4498
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  52.00   0.60   15.00    --  -17.65  57.00 -60.00  160
  2  ω    -25.00  21.20   0.60   15.00    --  -17.65 -99.00-150.00   77
  3  ω    -25.00  21.20   0.60   15.00    --  -17.65 -99.00  90.00   77
  4  ω    -25.00  21.20   0.60   15.00    --  -17.65 -99.00 150.00   77
  5  ω    -55.00  50.00   0.60   15.00    --   18.44 -77.00 -30.00  175
  6  ω    -52.00  44.00   0.60   15.00    --   18.44 -57.00-180.00  160
  7  ω     -4.00  90.20   0.60   15.00    --   18.44  38.00 120.00  157
  8  ω    -25.00  21.20   0.60   15.00    --  -17.65 -99.00 -60.00   77
  9  ω    -90.00   4.20   0.60   15.00    --  -17.65 -38.00 150.00  157
 10  ω     -8.00  88.00   0.60   15.00    --   18.44  57.00   0.00  160
 11  ω    -25.00   0.20   0.60   15.00    --   18.44 -99.00 120.00   42
 12  ω    -54.00  34.80   0.60   15.00    --   18.44 -38.00  60.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0674679000
_diffrn_orient_matrix_UB_12      0.0448547000
_diffrn_orient_matrix_UB_13      -0.0032541000
_diffrn_orient_matrix_UB_21      -0.0327922000
_diffrn_orient_matrix_UB_22      0.0045972000
_diffrn_orient_matrix_UB_23      -0.0365263000
_diffrn_orient_matrix_UB_31      -0.0250660000
_diffrn_orient_matrix_UB_32      0.0545057000
_diffrn_orient_matrix_UB_33      0.0143556000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5660
_reflns_number_total             6339

_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_refine_diff_density_max         1.025
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         6339
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0385P)²+1.6306P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0974
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C29(H29A,H29B), C31(H31A,
 H31B), C33(H33A,H33B), C35(H35A,H35B), C36(H36A,H36B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16),
 C19(H19), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C24(H24A,H24B,H24C), C28(H28A,H28B,H28C), C30(H30A,H30B,
 H30C), C32(H32A,H32B,H32C), C34(H34A,H34B,H34C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
C1 C 0.56062(18) 0.29388(16) 0.56237(9) 0.0166(3) Uani 1 1 d . . . . .
C2 C 0.44925(19) 0.21886(17) 0.50328(10) 0.0226(4) Uani 1 1 d . . . . .
H2 H 0.455032 0.230186 0.453608 0.027 Uiso 1 1 calc R . . . .
C3 C 0.3296(2) 0.12715(18) 0.51875(10) 0.0260(4) Uani 1 1 d . . . . .
H3 H 0.251316 0.075645 0.479481 0.031 Uiso 1 1 calc R . . . .
C4 C 0.32430(19) 0.11068(17) 0.59100(10) 0.0221(4) Uani 1 1 d . . . . .
H4 H 0.245480 0.045158 0.602171 0.027 Uiso 1 1 calc R . . . .
C5 C 0.43753(18) 0.19265(16) 0.64732(9) 0.0177(3) Uani 1 1 d . . . . .
C6 C 0.44649(18) 0.17705(16) 0.72693(10) 0.0188(3) Uani 1 1 d . . . . .
C7 C 0.3607(2) 0.06418(18) 0.74834(10) 0.0246(4) Uani 1 1 d . . . . .
H7 H 0.283547 0.000226 0.713372 0.029 Uiso 1 1 calc R . . . .
C8 C 0.3913(2) 0.04859(19) 0.82156(11) 0.0308(4) Uani 1 1 d . . . . .
H8 H 0.333989 -0.026186 0.837898 0.037 Uiso 1 1 calc R . . . .
C9 C 0.5060(2) 0.14215(19) 0.87136(11) 0.0289(4) Uani 1 1 d . . . . .
H9 H 0.530586 0.130852 0.921561 0.035 Uiso 1 1 calc R . . . .
C10 C 0.58430(19) 0.25317(17) 0.84613(9) 0.0205(4) Uani 1 1 d . . . . .
C11 C 0.7193(2) 0.35857(17) 0.89535(9) 0.0211(4) Uani 1 1 d . . . . .
C12 C 0.7208(2) 0.3564(2) 0.97801(10) 0.0291(4) Uani 1 1 d . . . . .
H12A H 0.737492 0.272262 0.990303 0.044 Uiso 1 1 calc GR . . . .
H12B H 0.624885 0.364280 0.989034 0.044 Uiso 1 1 calc GR . . . .
H12C H 0.801067 0.431187 1.007601 0.044 Uiso 1 1 calc GR . . . .
C13 C 0.86191(19) 0.33217(16) 0.87327(9) 0.0204(4) Uani 1 1 d . . . . .
C14 C 0.9789(2) 0.31223(19) 0.92276(10) 0.0276(4) Uani 1 1 d . . . . .
H14 H 0.974351 0.312611 0.973665 0.033 Uiso 1 1 calc R . . . .
C15 C 1.1023(2) 0.29182(19) 0.89638(11) 0.0300(4) Uani 1 1 d . . . . .
H15 H 1.184152 0.279899 0.929534 0.036 Uiso 1 1 calc R . . . .
C16 C 1.1064(2) 0.28876(18) 0.82210(10) 0.0256(4) Uani 1 1 d . . . . .
H16 H 1.189753 0.273778 0.803145 0.031 Uiso 1 1 calc R . . . .
C17 C 0.98437(19) 0.30837(16) 0.77562(9) 0.0190(3) Uani 1 1 d . . . . .
C18 C 0.96780(18) 0.29457(16) 0.69306(9) 0.0177(3) Uani 1 1 d . . . . .
C19 C 1.03336(19) 0.21170(17) 0.65359(10) 0.0225(4) Uani 1 1 d . . . . .
H19 H 1.104310 0.173194 0.678532 0.027 Uiso 1 1 calc R . . . .
C20 C 0.9926(2) 0.18674(18) 0.57707(10) 0.0246(4) Uani 1 1 d . . . . .
H20 H 1.036071 0.130794 0.548594 0.030 Uiso 1 1 calc R . . . .
C21 C 0.88891(19) 0.24315(17) 0.54211(10) 0.0202(4) Uani 1 1 d . . . . .
H21 H 0.857286 0.224342 0.489650 0.024 Uiso 1 1 calc R . . . .
C22 C 0.83140(17) 0.32850(15) 0.58555(9) 0.0154(3) Uani 1 1 d . . . . .
C23 C 0.70711(18) 0.38827(16) 0.55237(9) 0.0161(3) Uani 1 1 d . . . . .
C24 C 0.7070(2) 0.39782(17) 0.47031(9) 0.0217(4) Uani 1 1 d . . . . .
H24A H 0.805822 0.448694 0.465214 0.033 Uiso 1 1 calc GR . . . .
H24B H 0.632380 0.442915 0.451925 0.033 Uiso 1 1 calc GR . . . .
H24C H 0.682751 0.307946 0.441374 0.033 Uiso 1 1 calc GR . . . .
C25 C 0.7161(2) 0.49810(17) 0.87760(9) 0.0212(4) Uani 1 1 d . . . . .
H25A H 0.809540 0.563560 0.904889 0.025 Uiso 1 1 calc R . . . .
H25B H 0.713879 0.497003 0.823877 0.025 Uiso 1 1 calc R . . . .
C26 C 0.5840(2) 0.54519(18) 0.89738(10) 0.0260(4) Uani 1 1 d . . . . .
H26A H 0.587694 0.549017 0.951371 0.031 Uiso 1 1 calc R . . . .
H26B H 0.490381 0.478695 0.871163 0.031 Uiso 1 1 calc R . . . .
C27 C 0.7784(3) 0.9350(2) 0.92218(12) 0.0379(5) Uani 1 1 d . . . . .
H27A H 0.703377 0.962205 0.888052 0.046 Uiso 1 1 calc R . . . .
H27B H 0.877283 0.970189 0.909853 0.046 Uiso 1 1 calc R . . . .
C28 C 0.7803(4) 0.9906(2) 1.00036(13) 0.0577(7) Uani 1 1 d . . . . .
H28A H 0.813211 1.088179 1.007648 0.087 Uiso 1 1 calc GR . . . .
H28B H 0.849073 0.957786 1.034085 0.087 Uiso 1 1 calc GR . . . .
H28C H 0.679764 0.962349 1.010811 0.087 Uiso 1 1 calc GR . . . .
C29 C 0.4560(3) 0.6740(2) 0.73229(12) 0.0419(5) Uani 1 1 d . . . . .
H29A H 0.486208 0.693874 0.685198 0.050 Uiso 1 1 calc R . . . .
H29B H 0.396371 0.735244 0.746393 0.050 Uiso 1 1 calc R . . . .
C30 C 0.3612(3) 0.5331(3) 0.72025(13) 0.0536(7) Uani 1 1 d . . . . .
H30A H 0.280231 0.518359 0.677149 0.080 Uiso 1 1 calc GR . . . .
H30B H 0.319099 0.516892 0.764386 0.080 Uiso 1 1 calc GR . . . .
H30C H 0.422421 0.471815 0.711331 0.080 Uiso 1 1 calc GR . . . .
C31 C 0.9698(2) 0.6728(2) 0.76985(11) 0.0336(4) Uani 1 1 d . . . . .
H31A H 0.951249 0.579554 0.744978 0.040 Uiso 1 1 calc R . . . .
H31B H 0.874005 0.686868 0.779357 0.040 Uiso 1 1 calc R . . . .
C32 C 1.0795(3) 0.6986(3) 0.84100(12) 0.0491(6) Uani 1 1 d . . . . .
H32A H 1.176325 0.692177 0.830631 0.074 Uiso 1 1 calc GR . . . .
H32B H 1.044531 0.632528 0.871816 0.074 Uiso 1 1 calc GR . . . .
H32C H 1.089831 0.788273 0.867395 0.074 Uiso 1 1 calc GR . . . .
C33 C 0.8072(2) 0.93742(18) 0.71834(11) 0.0301(4) Uani 1 1 d . . . . .
H33A H 0.907641 0.999273 0.724330 0.036 Uiso 1 1 calc R . . . .
H33B H 0.794102 0.913421 0.767402 0.036 Uiso 1 1 calc R . . . .
C34 C 0.6917(2) 1.0037(2) 0.69052(15) 0.0469(6) Uani 1 1 d . . . . .
H34A H 0.706430 1.029107 0.642487 0.070 Uiso 1 1 calc GR . . . .
H34B H 0.700093 1.083626 0.726145 0.070 Uiso 1 1 calc GR . . . .
H34C H 0.592443 0.942082 0.684586 0.070 Uiso 1 1 calc GR . . . .
C35 C 0.86899(19) 0.62792(16) 0.58695(10) 0.0203(4) Uani 1 1 d . . . . .
H35A H 0.849767 0.647982 0.535957 0.024 Uiso 1 1 calc R . . . .
H35B H 0.949515 0.582321 0.589726 0.024 Uiso 1 1 calc R . . . .
C36 C 0.72778(18) 0.52798(15) 0.59711(9) 0.0161(3) Uani 1 1 d . . . . .
H36A H 0.639801 0.560420 0.580608 0.019 Uiso 1 1 calc R . . . .
H36B H 0.734435 0.521749 0.650423 0.019 Uiso 1 1 calc R . . . .
N1 N 0.55168(15) 0.28365(13) 0.63276(8) 0.0173(3) Uani 1 1 d . . . . .
N2 N 0.55122(15) 0.27142(14) 0.77601(8) 0.0188(3) Uani 1 1 d . . . . .
N3 N 0.86728(16) 0.33190(14) 0.80158(8) 0.0196(3) Uani 1 1 d . . . . .
N4 N 0.87305(15) 0.35567(13) 0.65934(7) 0.0165(3) Uani 1 1 d . . . . .
O1 O 0.45817(16) 0.75664(15) 0.89466(8) 0.0362(3) Uani 1 1 d . . . . .
O2 O 0.74205(16) 0.79080(13) 0.91318(8) 0.0352(3) Uani 1 1 d . . . . .
O3 O 0.58791(15) 0.69823(13) 0.78943(7) 0.0318(3) Uani 1 1 d . . . . .
O4 O 1.03778(15) 0.88601(13) 0.61862(8) 0.0319(3) Uani 1 1 d . . . . .
O5 O 1.03167(16) 0.76425(14) 0.72343(8) 0.0345(3) Uani 1 1 d . . . . .
O6 O 0.79367(13) 0.81776(12) 0.66592(7) 0.0235(3) Uani 1 1 d . . . . .
P1 P 0.93928(5) 0.78322(4) 0.64898(2) 0.01871(11) Uani 1 1 d . . . . .
P2 P 0.57947(5) 0.70490(5) 0.87416(3) 0.02476(12) 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
C1 C2 1.391(2) . ?
C1 C23 1.544(2) . ?
C1 N1 1.335(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.377(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(2) . ?
C5 C6 1.494(2) . ?
C5 N1 1.341(2) . ?
C6 C7 1.401(2) . ?
C6 N2 1.340(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.378(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.394(2) . ?
C10 C11 1.539(2) . ?
C10 N2 1.334(2) . ?
C11 C12 1.531(2) . ?
C11 C13 1.545(2) . ?
C11 C25 1.545(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.391(3) . ?
C13 N3 1.336(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.379(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.396(2) . ?
C17 C18 1.496(2) . ?
C17 N3 1.338(2) . ?
C18 C19 1.388(2) . ?
C18 N4 1.341(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.381(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.378(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.395(2) . ?
C22 C23 1.538(2) . ?
C22 N4 1.334(2) . ?
C23 C24 1.535(2) . ?
C23 C36 1.544(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.529(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 P2 1.7883(19) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.489(3) . ?
C27 O2 1.449(2) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.498(3) . ?
C29 O3 1.445(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.489(3) . ?
C31 O5 1.445(2) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.488(3) . ?
C33 O6 1.456(2) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.535(2) . ?
C35 P1 1.7844(17) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
O1 P2 1.4640(14) . ?
O2 P2 1.5797(14) . ?
O3 P2 1.5775(14) . ?
O4 P1 1.4725(13) . ?
O5 P1 1.5696(14) . ?
O6 P1 1.5726(13) . ?

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
C2 C1 C23 123.40(15) . . ?
N1 C1 C2 121.85(15) . . ?
N1 C1 C23 114.66(14) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.30(16) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.02(16) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.9 . . ?
C3 C4 C5 118.25(16) . . ?
C5 C4 H4 120.9 . . ?
C4 C5 C6 122.22(15) . . ?
N1 C5 C4 121.91(16) . . ?
N1 C5 C6 115.68(14) . . ?
C7 C6 C5 121.98(15) . . ?
N2 C6 C5 115.86(14) . . ?
N2 C6 C7 121.88(16) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 C6 118.11(17) . . ?
C8 C7 H7 120.9 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.93(17) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.7 . . ?
C8 C9 C10 118.53(17) . . ?
C10 C9 H9 120.7 . . ?
C9 C10 C11 122.80(16) . . ?
N2 C10 C9 121.77(16) . . ?
N2 C10 C11 115.35(14) . . ?
C10 C11 C13 107.87(13) . . ?
C10 C11 C25 109.33(14) . . ?
C12 C11 C10 111.71(14) . . ?
C12 C11 C13 111.63(15) . . ?
C12 C11 C25 109.96(14) . . ?
C25 C11 C13 106.16(13) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C11 124.18(16) . . ?
N3 C13 C11 114.70(14) . . ?
N3 C13 C14 121.11(17) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 C13 118.73(17) . . ?
C15 C14 H14 120.6 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.14(17) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 121.0 . . ?
C15 C16 C17 117.94(17) . . ?
C17 C16 H16 121.0 . . ?
C16 C17 C18 123.41(16) . . ?
N3 C17 C16 121.83(16) . . ?
N3 C17 C18 114.60(14) . . ?
C19 C18 C17 121.79(15) . . ?
N4 C18 C17 115.57(14) . . ?
N4 C18 C19 122.26(16) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 C18 118.21(16) . . ?
C20 C19 H19 120.9 . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.87(16) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 120.8 . . ?
C20 C21 C22 118.47(16) . . ?
C22 C21 H21 120.8 . . ?
C21 C22 C23 122.34(15) . . ?
N4 C22 C21 121.93(15) . . ?
N4 C22 C23 115.55(14) . . ?
C1 C23 C36 109.06(13) . . ?
C22 C23 C1 105.25(12) . . ?
C22 C23 C36 109.53(13) . . ?
C24 C23 C1 111.53(13) . . ?
C24 C23 C22 111.41(13) . . ?
C24 C23 C36 109.93(13) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C11 C25 H25A 108.6 . . ?
C11 C25 H25B 108.6 . . ?
H25A C25 H25B 107.6 . . ?
C26 C25 C11 114.52(14) . . ?
C26 C25 H25A 108.6 . . ?
C26 C25 H25B 108.6 . . ?
C25 C26 H26A 108.8 . . ?
C25 C26 H26B 108.8 . . ?
C25 C26 P2 113.87(12) . . ?
H26A C26 H26B 107.7 . . ?
P2 C26 H26A 108.8 . . ?
P2 C26 H26B 108.8 . . ?
H27A C27 H27B 108.2 . . ?
C28 C27 H27A 109.8 . . ?
C28 C27 H27B 109.8 . . ?
O2 C27 H27A 109.8 . . ?
O2 C27 H27B 109.8 . . ?
O2 C27 C28 109.36(18) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
H29A C29 H29B 107.9 . . ?
C30 C29 H29A 109.1 . . ?
C30 C29 H29B 109.1 . . ?
O3 C29 H29A 109.1 . . ?
O3 C29 H29B 109.1 . . ?
O3 C29 C30 112.37(19) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
H31A C31 H31B 108.5 . . ?
C32 C31 H31A 110.2 . . ?
C32 C31 H31B 110.2 . . ?
O5 C31 H31A 110.2 . . ?
O5 C31 H31B 110.2 . . ?
O5 C31 C32 107.72(17) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
H33A C33 H33B 108.2 . . ?
C34 C33 H33A 109.8 . . ?
C34 C33 H33B 109.8 . . ?
O6 C33 H33A 109.8 . . ?
O6 C33 H33B 109.8 . . ?
O6 C33 C34 109.56(17) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
H35A C35 H35B 107.0 . . ?
C36 C35 H35A 107.5 . . ?
C36 C35 H35B 107.5 . . ?
C36 C35 P1 119.26(12) . . ?
P1 C35 H35A 107.5 . . ?
P1 C35 H35B 107.5 . . ?
C23 C36 H36A 109.3 . . ?
C23 C36 H36B 109.3 . . ?
C35 C36 C23 111.49(13) . . ?
C35 C36 H36A 109.3 . . ?
C35 C36 H36B 109.3 . . ?
H36A C36 H36B 108.0 . . ?
C1 N1 C5 119.50(14) . . ?
C10 N2 C6 119.55(15) . . ?
C13 N3 C17 120.21(15) . . ?
C22 N4 C18 119.08(14) . . ?
C27 O2 P2 119.69(13) . . ?
C29 O3 P2 121.84(13) . . ?
C31 O5 P1 122.93(13) . . ?
C33 O6 P1 119.09(12) . . ?
O4 P1 C35 113.11(8) . . ?
O4 P1 O5 107.25(8) . . ?
O4 P1 O6 114.79(8) . . ?
O5 P1 C35 110.21(8) . . ?
O5 P1 O6 108.26(8) . . ?
O6 P1 C35 103.11(7) . . ?
O1 P2 C26 115.91(9) . . ?
O1 P2 O2 115.46(8) . . ?
O1 P2 O3 114.09(8) . . ?
O2 P2 C26 100.73(8) . . ?
O3 P2 C26 107.13(8) . . ?
O3 P2 O2 101.77(8) . . ?

_olex2_date_sample_data_collection 2018-10-16
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.233
_oxdiff_exptl_absorpt_empirical_full_min 0.796
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_Co(III)-9
_database_code_depnum_ccdc_archive 'CCDC 1958071'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;Department of Chemistry, University of Zurich
Switzerland
;
_audit_update_record             
;
2019-10-08 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

_audit_creation_date             2017-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C24 H20 Br2 Co N4 O2, 0.5(C2 H4 O6 S2), C2 H6 O S, H2 O'
_chemical_formula_sum            'C27 H30 Br2 Co N4 O7 S2'
_chemical_formula_weight         805.42
_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 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1545(3)
_cell_length_b                   11.7917(5)
_cell_length_c                   16.3115(4)
_cell_angle_alpha                107.981(3)
_cell_angle_beta                 96.136(3)
_cell_angle_gamma                103.720(3)
_cell_volume                     1421.47(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10672
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      78.4
_cell_measurement_theta_min      2.9
_shelx_estimated_absorpt_T_max   0.827
_shelx_estimated_absorpt_T_min   0.410
_exptl_absorpt_coefficient_mu    9.878
_exptl_absorpt_correction_T_max  0.877
_exptl_absorpt_correction_T_min  0.477
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.13a (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.882
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             810
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0091
0 0 1 0.0141
0 -1 0 0.0040
0 1 0 0.0110
5 2 -2 0.0374
-5 -2 2 0.0474

_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02

_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21345
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.504
_diffrn_reflns_theta_min         2.904
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00  21.00   0.50    8.00    --  -51.81  77.00   0.00  188
  2  ω    -77.00 -11.00   0.50   32.00    --  -86.25  45.00 -30.00  132
  3  ω    -90.00 -10.00   0.50   32.00    --  -86.25 111.00  60.00  160
  4  ω    -95.00  -9.00   0.50    8.00    --  -51.81 125.00 120.00  172
  5  ω   -131.00 -43.00   0.50    8.00    --  -51.81 -19.00 120.00  176
  6  ω   -127.00 -82.00   0.50    8.00    --  -51.81 -99.00  90.00   90
  7  ω   -127.00 -82.00   0.50    8.00    --  -51.81 -99.00   0.00   90
  8  ω   -127.00 -82.00   0.50    8.00    --  -51.81 -99.00 -60.00   90
  9  ω   -124.00 -38.00   0.50    8.00    --  -51.81 -57.00-150.00  172
 10  ω   -126.00 -70.00   0.50    8.00    --  -51.81-125.00-180.00  112
 11  ω     35.00 129.00   0.50   32.00    --  107.75 -77.00  90.00  188
 12  ω     72.00 105.00   0.50   32.00    --  107.75 -94.00  90.00   66
 13  ω     71.00 113.00   0.50   32.00    --  107.75-111.00  60.00   84
 14  ω     57.00 106.00   0.50   32.00    --  107.75-111.00  90.00   98
 15  ω     38.00  69.00   0.50   32.00    --  107.75 -94.00  90.00   62
 16  ω     32.00  77.00   0.50   32.00    --  107.75 -45.00 150.00   90
 17  ω     41.00  67.00   0.50   32.00    --  107.75 -30.00  90.00   52
 18  ω     45.00  70.00   0.50   32.00    --  107.75 -15.00  30.00   50
 19  ω     83.00 117.00   0.50   32.00    --  107.75 -15.00  30.00   68
 20  ω    106.00 174.00   0.50   32.00    --  107.75  15.00  30.00  136
 21  ω    121.00 171.00   0.50   32.00    --  107.75  30.00  60.00  100
 22  ω     98.00 178.00   0.50   32.00    --  107.75  15.00 -60.00  160
 23  ω     83.00 117.00   0.50   32.00    --  107.75 -61.00 -60.00   68
 24  ω     82.00 114.00   0.50   32.00    --  107.75-111.00 -90.00   64
 25  ω     69.00 115.00   0.50   32.00    --  107.75-111.00-180.00   92
 26  ω     45.00 127.00   0.50   32.00    --  107.75 -77.00 -60.00  164
 27  ω     48.00  97.00   0.50   32.00    --  107.75 -94.00 -90.00   98
 28  ω     46.00 108.00   0.50   32.00    --  107.75 -94.00 -60.00  124
 29  ω     38.00  65.00   0.50   32.00    --  107.75 -61.00 -60.00   54
 30  ω     34.00  61.00   0.50   32.00    --  107.75 -30.00-120.00   54
 31  ω     34.00  74.00   0.50   32.00    --  107.75 -45.00 -60.00   80
 32  ω     32.00  69.00   0.50   32.00    --  107.75 -30.00   0.00   74
 33  ω     33.00  66.00   0.50   32.00    --  107.75 -30.00 -60.00   66
 34  ω     34.00  66.00   0.50   32.00    --  107.75 -30.00 -30.00   64
 35  ω     33.00  71.00   0.50   32.00    --  107.75 -94.00-120.00   76
 36  ω     32.00 102.00   0.50   32.00    --  107.75 -94.00-180.00  140
 37  ω     38.00  79.00   0.50   32.00    --  107.75-111.00 -90.00   82
 38  ω     35.00  72.00   0.50   32.00    --  107.75 -45.00  60.00   74
 39  ω     32.00  71.00   0.50   32.00    --  107.75 -45.00  90.00   78
 40  ω     36.00  62.00   0.50   32.00    --  107.75 -30.00 120.00   52
 41  ω     35.00  66.00   0.50   32.00    --  107.75 -30.00 150.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0183580000
_diffrn_orient_matrix_UB_12      0.1329698000
_diffrn_orient_matrix_UB_13      0.0295080000
_diffrn_orient_matrix_UB_21      -0.1876882000
_diffrn_orient_matrix_UB_22      -0.0512202000
_diffrn_orient_matrix_UB_23      0.0077570000
_diffrn_orient_matrix_UB_31      0.0612257000
_diffrn_orient_matrix_UB_32      0.0154552000
_diffrn_orient_matrix_UB_33      0.0965306000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4879
_reflns_number_total             5801

_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       'CrysAlisPro 1.171.39.13a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.13a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.13a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_refine_diff_density_max         1.287
_refine_diff_density_min         -0.724
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         5801
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.030
_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)+(0.0510P)²+3.0667P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1077
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H) groups, All O(H) groups
2. Restrained distances
 O7-H7A
 0.82 with sigma of 0.01
 O7-H7B
 0.82 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C16(H16),
 C19(H19), C20(H20), C21(H21)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Br1 Br 0.70421(5) 0.60774(4) 0.37686(3) 0.02855(12) Uani 1 1 d . . . . .
Br2 Br 0.27846(5) 0.34155(4) 0.12031(2) 0.02550(11) Uani 1 1 d . . . . .
C1 C 0.6765(4) 0.6252(3) 0.1548(2) 0.0198(7) Uani 1 1 d . . . . .
C2 C 0.8193(5) 0.6609(4) 0.1193(2) 0.0247(7) Uani 1 1 d . . . . .
H2 H 0.839459 0.733610 0.106006 0.030 Uiso 1 1 calc R . . . .
C3 C 0.9315(5) 0.5889(4) 0.1038(3) 0.0272(8) Uani 1 1 d . . . . .
H3 H 1.027561 0.612708 0.080343 0.033 Uiso 1 1 calc R . . . .
C4 C 0.8990(5) 0.4805(4) 0.1237(2) 0.0244(7) Uani 1 1 d . . . . .
H4 H 0.970276 0.428858 0.112088 0.029 Uiso 1 1 calc R . . . .
C5 C 0.7583(4) 0.4512(3) 0.1612(2) 0.0202(7) Uani 1 1 d . . . . .
C6 C 0.7167(4) 0.3427(3) 0.1895(2) 0.0208(7) Uani 1 1 d . . . . .
C7 C 0.7962(5) 0.2494(4) 0.1682(3) 0.0273(8) Uani 1 1 d . . . . .
H7 H 0.878957 0.251367 0.133234 0.033 Uiso 1 1 calc R . . . .
C8 C 0.7504(5) 0.1525(4) 0.2001(3) 0.0310(9) Uani 1 1 d . . . . .
H8 H 0.800521 0.087647 0.186184 0.037 Uiso 1 1 calc R . . . .
C9 C 0.6290(5) 0.1540(4) 0.2529(3) 0.0269(8) Uani 1 1 d . . . . .
H9 H 0.598028 0.090025 0.275293 0.032 Uiso 1 1 calc R . . . .
C10 C 0.5530(5) 0.2498(3) 0.2729(2) 0.0208(7) Uani 1 1 d . . . . .
C11 C 0.4392(5) 0.2542(4) 0.3413(2) 0.0240(7) Uani 1 1 d . . . . .
C12 C 0.5597(5) 0.3132(4) 0.4321(2) 0.0286(8) Uani 1 1 d . . . . .
H12A H 0.492620 0.315850 0.477154 0.043 Uiso 1 1 calc GR . . . .
H12B H 0.624746 0.396172 0.439323 0.043 Uiso 1 1 calc GR . . . .
H12C H 0.637006 0.264297 0.436270 0.043 Uiso 1 1 calc GR . . . .
C13 C 0.3071(4) 0.3270(3) 0.3439(2) 0.0219(7) Uani 1 1 d . . . . .
C14 C 0.1683(5) 0.2948(4) 0.3834(3) 0.0286(8) Uani 1 1 d . . . . .
H14 H 0.150411 0.223896 0.398954 0.034 Uiso 1 1 calc R . . . .
C15 C 0.0571(5) 0.3678(4) 0.3995(3) 0.0307(9) Uani 1 1 d . . . . .
H15 H -0.036653 0.345961 0.425038 0.037 Uiso 1 1 calc R . . . .
C16 C 0.0877(5) 0.4741(4) 0.3771(3) 0.0282(8) Uani 1 1 d . . . . .
H16 H 0.016600 0.525907 0.388499 0.034 Uiso 1 1 calc R . . . .
C17 C 0.2256(5) 0.5013(4) 0.3374(2) 0.0224(7) Uani 1 1 d . . . . .
C18 C 0.2673(5) 0.6099(3) 0.3092(2) 0.0223(7) Uani 1 1 d . . . . .
C19 C 0.1913(5) 0.7055(4) 0.3324(3) 0.0294(8) Uani 1 1 d . . . . .
H19 H 0.110758 0.704971 0.368647 0.035 Uiso 1 1 calc R . . . .
C20 C 0.2380(6) 0.8014(4) 0.3004(3) 0.0327(9) Uani 1 1 d . . . . .
H20 H 0.189892 0.867293 0.315277 0.039 Uiso 1 1 calc R . . . .
C21 C 0.3569(5) 0.7988(4) 0.2462(3) 0.0279(8) Uani 1 1 d . . . . .
H21 H 0.387964 0.862734 0.223788 0.033 Uiso 1 1 calc R . . . .
C22 C 0.4302(5) 0.7013(3) 0.2249(2) 0.0218(7) Uani 1 1 d . . . . .
C23 C 0.5413(5) 0.6959(3) 0.1548(2) 0.0212(7) Uani 1 1 d . . . . .
C24 C 0.4165(5) 0.6293(4) 0.0654(2) 0.0270(8) Uani 1 1 d . . . . .
H24A H 0.331576 0.672532 0.061347 0.040 Uiso 1 1 calc GR . . . .
H24B H 0.360538 0.545362 0.060289 0.040 Uiso 1 1 calc GR . . . .
H24C H 0.479527 0.628565 0.018889 0.040 Uiso 1 1 calc GR . . . .
Co1 Co 0.49080(7) 0.47536(5) 0.24855(4) 0.01638(13) Uani 1 1 d . . . . .
N1 N 0.6506(4) 0.5239(3) 0.17845(18) 0.0178(6) Uani 1 1 d . . . . .
N2 N 0.5941(4) 0.3428(3) 0.23986(18) 0.0188(6) Uani 1 1 d . . . . .
N3 N 0.3320(4) 0.4282(3) 0.31937(18) 0.0196(6) Uani 1 1 d . . . . .
N4 N 0.3880(4) 0.6089(3) 0.25766(18) 0.0182(6) Uani 1 1 d . . . . .
O1 O 0.3551(4) 0.1302(3) 0.33444(18) 0.0289(6) Uani 1 1 d . . . . .
H1 H 0.293812 0.093074 0.285569 0.043 Uiso 1 1 calc GR . . . .
O2 O 0.6267(4) 0.8193(2) 0.16438(19) 0.0289(6) Uani 1 1 d . . . . .
H2A H 0.601918 0.831394 0.118344 0.043 Uiso 1 1 calc GR . . . .
C26 C 0.6876(8) 0.9288(5) 0.4780(4) 0.0541(13) Uani 1 1 d . . . . .
H26A H 0.783499 0.910584 0.505455 0.081 Uiso 1 1 calc GR . . . .
H26B H 0.605999 0.852583 0.439754 0.081 Uiso 1 1 calc GR . . . .
H26C H 0.633613 0.971744 0.522390 0.081 Uiso 1 1 calc GR . . . .
H7A H 0.417(8) 0.111(7) 0.014(4) 0.081 Uiso 1 1 d DR . . . .
H7B H 0.539(7) 0.088(6) -0.040(5) 0.081 Uiso 1 1 d DR . . . .
C27 C 0.8795(7) 0.9335(6) 0.3546(3) 0.0528(13) Uani 1 1 d . . . . .
H27A H 0.925400 0.970640 0.314178 0.079 Uiso 1 1 calc GR . . . .
H27B H 0.805187 0.851204 0.322643 0.079 Uiso 1 1 calc GR . . . .
H27C H 0.972273 0.928840 0.393872 0.079 Uiso 1 1 calc GR . . . .
O6 O 0.8883(5) 1.1394(4) 0.4770(3) 0.0596(10) Uani 1 1 d . . . . .
S2 S 0.76166(17) 1.02464(12) 0.41569(8) 0.0454(3) Uani 1 1 d . . . . .
C25 C -0.0030(5) 0.0087(4) 0.0475(3) 0.0326(9) Uani 1 1 d . . . . .
H25A H -0.118086 -0.032663 0.051766 0.039 Uiso 1 1 calc R . . . .
H25B H 0.021050 0.096710 0.080457 0.039 Uiso 1 1 calc R . . . .
O3 O 0.1059(4) -0.1823(3) 0.0451(2) 0.0401(7) Uani 1 1 d . . . . .
O4 O 0.1242(4) -0.0238(3) 0.1861(2) 0.0435(8) Uani 1 1 d . . . . .
O5 O 0.3167(4) 0.0167(3) 0.0899(2) 0.0406(7) Uani 1 1 d . . . . .
S1 S 0.14711(13) -0.05140(10) 0.09532(7) 0.0315(2) Uani 1 1 d . . . . .
O7 O 0.4690(5) 0.1275(4) -0.0237(3) 0.0568(10) Uani 1 1 d 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 Co1 2.4003(7) . ?
Br2 Co1 2.3990(7) . ?
C1 C2 1.389(5) . ?
C1 C23 1.532(5) . ?
C1 N1 1.343(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.386(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(5) . ?
C5 C6 1.469(5) . ?
C5 N1 1.359(4) . ?
C6 C7 1.380(5) . ?
C6 N2 1.360(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(5) . ?
C10 C11 1.523(5) . ?
C10 N2 1.354(4) . ?
C11 C12 1.539(5) . ?
C11 C13 1.525(5) . ?
C11 O1 1.424(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.395(5) . ?
C13 N3 1.349(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.384(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(5) . ?
C17 C18 1.470(5) . ?
C17 N3 1.354(4) . ?
C18 C19 1.384(5) . ?
C18 N4 1.361(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.378(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.387(5) . ?
C22 C23 1.528(5) . ?
C22 N4 1.347(5) . ?
C23 C24 1.541(5) . ?
C23 O2 1.408(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
Co1 N1 1.924(3) . ?
Co1 N2 1.920(3) . ?
Co1 N3 1.922(3) . ?
Co1 N4 1.927(3) . ?
O1 H1 0.8200 . ?
O2 H2A 0.8200 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C26 S2 1.787(5) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C27 S2 1.762(5) . ?
O6 S2 1.476(4) . ?
C25 C25 1.507(8) 2 ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 S1 1.777(4) . ?
O3 S1 1.442(3) . ?
O4 S1 1.458(3) . ?
O5 S1 1.452(3) . ?
O7 H7A 0.827(10) . ?
O7 H7B 0.828(10) . ?

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
C2 C1 C23 117.2(3) . . ?
N1 C1 C2 120.4(3) . . ?
N1 C1 C23 121.9(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.5 . . ?
C2 C3 C4 119.1(3) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.3(3) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C6 123.1(3) . . ?
N1 C5 C4 122.5(3) . . ?
N1 C5 C6 114.4(3) . . ?
C7 C6 C5 123.3(3) . . ?
N2 C6 C5 114.1(3) . . ?
N2 C6 C7 122.5(3) . . ?
C6 C7 H7 120.7 . . ?
C6 C7 C8 118.7(3) . . ?
C8 C7 H7 120.7 . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.8(3) . . ?
C9 C8 H8 120.6 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 117.3(3) . . ?
N2 C10 C9 120.7(3) . . ?
N2 C10 C11 121.6(3) . . ?
C10 C11 C12 107.0(3) . . ?
C10 C11 C13 119.1(3) . . ?
C13 C11 C12 106.3(3) . . ?
O1 C11 C10 108.8(3) . . ?
O1 C11 C12 105.6(3) . . ?
O1 C11 C13 109.3(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C11 117.0(3) . . ?
N3 C13 C11 122.2(3) . . ?
N3 C13 C14 120.3(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.2(4) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 119.0(3) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 H16 120.7 . . ?
C17 C16 C15 118.6(4) . . ?
C17 C16 H16 120.7 . . ?
C16 C17 C18 123.0(3) . . ?
N3 C17 C16 122.6(3) . . ?
N3 C17 C18 114.3(3) . . ?
C19 C18 C17 123.5(3) . . ?
N4 C18 C17 114.1(3) . . ?
N4 C18 C19 122.4(3) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 C18 118.4(3) . . ?
C20 C19 H19 120.8 . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.4(4) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.3(4) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C23 117.0(3) . . ?
N4 C22 C21 120.5(3) . . ?
N4 C22 C23 122.1(3) . . ?
C1 C23 C24 106.4(3) . . ?
C22 C23 C1 117.7(3) . . ?
C22 C23 C24 106.3(3) . . ?
O2 C23 C1 108.0(3) . . ?
O2 C23 C22 107.4(3) . . ?
O2 C23 C24 111.1(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
Br2 Co1 Br1 179.50(3) . . ?
N1 Co1 Br1 88.11(9) . . ?
N1 Co1 Br2 91.90(9) . . ?
N1 Co1 N4 95.06(12) . . ?
N2 Co1 Br1 90.26(9) . . ?
N2 Co1 Br2 89.24(9) . . ?
N2 Co1 N1 84.88(12) . . ?
N2 Co1 N3 95.37(12) . . ?
N2 Co1 N4 179.74(14) . . ?
N3 Co1 Br1 91.45(9) . . ?
N3 Co1 Br2 88.53(9) . . ?
N3 Co1 N1 179.51(14) . . ?
N3 Co1 N4 84.69(12) . . ?
N4 Co1 Br1 89.48(9) . . ?
N4 Co1 Br2 91.01(9) . . ?
C1 N1 C5 119.3(3) . . ?
C1 N1 Co1 127.4(2) . . ?
C5 N1 Co1 112.9(2) . . ?
C6 N2 Co1 113.1(2) . . ?
C10 N2 C6 118.6(3) . . ?
C10 N2 Co1 128.2(2) . . ?
C13 N3 C17 119.2(3) . . ?
C13 N3 Co1 127.2(2) . . ?
C17 N3 Co1 113.2(2) . . ?
C18 N4 Co1 112.9(2) . . ?
C22 N4 C18 119.0(3) . . ?
C22 N4 Co1 127.9(2) . . ?
C11 O1 H1 109.5 . . ?
C23 O2 H2A 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
S2 C26 H26A 109.5 . . ?
S2 C26 H26B 109.5 . . ?
S2 C26 H26C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
S2 C27 H27A 109.5 . . ?
S2 C27 H27B 109.5 . . ?
S2 C27 H27C 109.5 . . ?
C27 S2 C26 98.3(3) . . ?
O6 S2 C26 107.4(3) . . ?
O6 S2 C27 106.7(3) . . ?
C25 C25 H25A 109.1 2 . ?
C25 C25 H25B 109.1 2 . ?
C25 C25 S1 112.5(4) 2 . ?
H25A C25 H25B 107.8 . . ?
S1 C25 H25A 109.1 . . ?
S1 C25 H25B 109.1 . . ?
O3 S1 C25 107.3(2) . . ?
O3 S1 O4 114.41(19) . . ?
O3 S1 O5 111.9(2) . . ?
O4 S1 C25 104.2(2) . . ?
O5 S1 C25 106.65(19) . . ?
O5 S1 O4 111.6(2) . . ?
H7A O7 H7B 117(7) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O4 0.82 1.92 2.718(4) 164.8 . yes
O2 H2A O7 0.82 1.83 2.646(5) 172.3 2_665 yes
O7 H7A O5 0.827(10) 2.02(3) 2.812(5) 160(7) . yes
O7 H7B O5 0.828(10) 1.967(14) 2.791(5) 173(7) 2_655 yes


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_Co(II)-9
_database_code_depnum_ccdc_archive 'CCDC 1958072'
loop_
_audit_author_name
_audit_author_address
'Olivier Blacque'
;Department of Chemistry, University of Zurich
Switzerland
;
_audit_update_record             
;
2019-10-08 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

_audit_creation_date             2017-11-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 Br2 Co N4 O2, 2(C H4 O)'
_chemical_formula_sum            'C26 H28 Br2 Co N4 O4'
_chemical_formula_weight         679.27
_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 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.0833(1)
_cell_length_b                   11.8214(1)
_cell_length_c                   13.6272(1)
_cell_angle_alpha                90
_cell_angle_beta                 95.751(1)
_cell_angle_gamma                90
_cell_volume                     1295.61(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    16539
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      78.7740
_cell_measurement_theta_min      4.9410
_shelx_estimated_absorpt_T_max   0.838
_shelx_estimated_absorpt_T_min   0.305
_exptl_absorpt_coefficient_mu    9.148
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_correction_T_min  0.477
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.13a (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             682
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 1 0.0201
5 -1 -3 0.0701
-5 1 3 0.0861
0 1 -1 0.0044
0 -1 1 0.0124
0 -1 -1 0.0111

_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02

_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26383
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.501
_diffrn_reflns_theta_min         4.963
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     36.00 124.00   0.50    3.00    --   50.71  57.00 -30.00  176
  2  ω     99.00 178.00   0.50   12.00    --  107.75 111.00-120.00  158
  3  ω     95.00 178.00   0.50   12.00    --  107.75  15.00-120.00  166
  4  ω     95.00 178.00   0.50   12.00    --  107.75  15.00 -60.00  166
  5  ω     95.00 178.00   0.50   12.00    --  107.75  15.00   0.00  166
  6  ω     95.00 178.00   0.50   12.00    --  107.75  15.00-150.00  166
  7  ω     91.00 178.00   0.50   12.00    --  107.75  61.00  30.00  174
  8  ω     94.00 178.00   0.50   12.00    --  107.75  30.00  30.00  168
  9  ω     94.00 178.00   0.50   12.00    --  107.75  30.00 120.00  168
 10  ω     94.00 178.00   0.50   12.00    --  107.75  45.00  30.00  168
 11  ω     94.00 178.00   0.50   12.00    --  107.75  30.00  90.00  168
 12  ω     94.00 178.00   0.50   12.00    --  107.75  30.00  60.00  168
 13  ω     94.00 178.00   0.50   12.00    --  107.75  45.00  60.00  168
 14  ω     92.00 178.00   0.50   12.00    --  107.75  58.00  80.00  172
 15  ω     31.00 108.00   0.50   12.00    --  107.75 -94.00-180.00  154
 16  ω     29.00  69.00   0.50   12.00    --  107.75 -30.00-150.00   80
 17  ω     32.00  77.00   0.50   12.00    --  107.75 -45.00-150.00   90
 18  ω     34.00 130.00   0.50   12.00    --  107.75 -77.00-150.00  192
 19  ω     31.00 115.00   0.50   12.00    --  107.75-111.00-180.00  168
 20  ω     32.00  77.00   0.50   12.00    --  107.75 -45.00-180.00   90
 21  ω     29.00  69.00   0.50   12.00    --  107.75 -30.00 -90.00   80
 22  ω     31.00 108.00   0.50   12.00    --  107.75 -94.00-150.00  154
 23  ω     31.00 115.00   0.50   12.00    --  107.75-111.00 -60.00  168
 24  ω     32.00  77.00   0.50   12.00    --  107.75 -45.00  60.00   90
 25  ω     31.00 115.00   0.50   12.00    --  107.75-111.00  60.00  168
 26  ω     32.00  77.00   0.50   12.00    --  107.75 -45.00 150.00   90
 27  ω     29.00  69.00   0.50   12.00    --  107.75 -30.00 150.00   80
 28  ω     31.00 108.00   0.50   12.00    --  107.75 -94.00  90.00  154
 29  ω     28.00 124.00   0.50    3.00    --   50.71  77.00-120.00  192
 30  ω     28.00 124.00   0.50    3.00    --   50.71  77.00-180.00  192
 31  ω    -63.00  27.00   0.50    3.00    --  -50.71  38.00 -90.00  180
 32  ω    -66.00  22.00   0.50    3.00    --  -50.71  57.00   0.00  176
 33  ω    -63.00  27.00   0.50    3.00    --  -50.71  38.00-180.00  180
 34  ω    -90.00  -9.00   0.50   12.00    --  -86.25 111.00 -30.00  162
 35  ω   -128.00 -39.00   0.50    3.00    --  -50.71 -38.00  30.00  178
 36  ω   -127.00 -82.00   0.50    3.00    --  -50.71 -99.00-120.00   90
 37  ω   -127.00 -82.00   0.50    3.00    --  -50.71 -99.00-180.00   90
 38  ω   -162.00 -73.00   0.50   12.00    --  -86.25 -45.00  60.00  178
 39  ω   -160.00 -72.00   0.50   12.00    --  -86.25 -55.00 105.43  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0781732000
_diffrn_orient_matrix_UB_12      0.0724497000
_diffrn_orient_matrix_UB_13      -0.0772511000
_diffrn_orient_matrix_UB_21      -0.1588910000
_diffrn_orient_matrix_UB_22      0.0725191000
_diffrn_orient_matrix_UB_23      -0.0139004000
_diffrn_orient_matrix_UB_31      0.0730712000
_diffrn_orient_matrix_UB_32      0.0804787000
_diffrn_orient_matrix_UB_33      0.0821273000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2495
_reflns_number_total             2644

_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       'CrysAlisPro 1.171.39.13a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.13a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.13a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.952
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2644
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²+1.6856P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0942
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 O1-H1 = O2-H2A
 0.82 with sigma of 0.005
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Br1 Br 0.62172(4) 0.66795(3) 0.38496(2) 0.03544(13) Uani 1 1 d . . . . .
C1 C 0.6252(3) 0.3145(3) 0.3835(2) 0.0318(6) Uani 1 1 d . . . . .
C2 C 0.7416(4) 0.2307(3) 0.3689(2) 0.0384(7) Uani 1 1 d . . . . .
H2 H 0.720514 0.178672 0.318010 0.046 Uiso 1 1 calc R . . . .
C3 C 0.8869(4) 0.2250(3) 0.4296(3) 0.0417(7) Uani 1 1 d . . . . .
H3 H 0.964989 0.169338 0.420121 0.050 Uiso 1 1 calc R . . . .
C4 C 0.9168(4) 0.3026(3) 0.5051(2) 0.0346(6) Uani 1 1 d . . . . .
H4 H 1.014602 0.299948 0.547282 0.042 Uiso 1 1 calc R . . . .
C5 C 0.7979(3) 0.3843(2) 0.5165(2) 0.0275(6) Uani 1 1 d . . . . .
C6 C 0.8165(3) 0.4714(2) 0.5933(2) 0.0266(5) Uani 1 1 d . . . . .
C7 C 0.9635(4) 0.4912(2) 0.6518(2) 0.0316(6) Uani 1 1 d . . . . .
H7 H 1.057781 0.448177 0.644478 0.038 Uiso 1 1 calc R . . . .
C8 C 0.9670(4) 0.5762(3) 0.7211(2) 0.0366(7) Uani 1 1 d . . . . .
H8 H 1.064651 0.591953 0.760791 0.044 Uiso 1 1 calc R . . . .
C9 C 0.8251(4) 0.6376(3) 0.7312(2) 0.0365(7) Uani 1 1 d . . . . .
H9 H 0.826159 0.694532 0.778315 0.044 Uiso 1 1 calc R . . . .
C10 C 0.6801(4) 0.6143(3) 0.6707(2) 0.0316(6) Uani 1 1 d . . . . .
C11 C 0.5210(4) 0.6742(3) 0.6955(2) 0.0380(7) Uani 1 1 d . . . . .
C12 C 0.4567(4) 0.6083(4) 0.7824(2) 0.0469(8) Uani 1 1 d . . . . .
H12A H 0.543182 0.603872 0.835916 0.070 Uiso 1 1 calc GR . . . .
H12B H 0.424689 0.533341 0.761050 0.070 Uiso 1 1 calc GR . . . .
H12C H 0.362329 0.646896 0.803991 0.070 Uiso 1 1 calc GR . . . .
Co1 Co 0.500000 0.500000 0.500000 0.02586(17) Uani 1 2 d S T P . .
N1 N 0.6764(3) 0.5338(2) 0.60118(17) 0.0269(5) Uani 1 1 d . . . . .
N2 N 0.6520(3) 0.3892(2) 0.45735(17) 0.0272(5) Uani 1 1 d . . . . .
O1 O 0.5643(3) 0.7835(2) 0.7329(2) 0.0505(6) Uani 1 1 d D . . . .
C13 C 0.7110(8) 0.9634(5) 0.5102(4) 0.0810(15) Uani 1 1 d . . . . .
H13A H 0.628181 0.973292 0.455310 0.121 Uiso 1 1 calc GR . . . .
H13B H 0.819235 0.961393 0.486998 0.121 Uiso 1 1 calc GR . . . .
H13C H 0.705406 1.025196 0.555449 0.121 Uiso 1 1 calc GR . . . .
O2 O 0.6819(5) 0.8609(3) 0.5586(3) 0.0735(9) Uani 1 1 d D . . . .
H1 H 0.601(8) 0.808(5) 0.683(3) 0.110 Uiso 1 1 d DR . . . .
H2A H 0.648(8) 0.815(4) 0.516(3) 0.110 Uiso 1 1 d DR . . . .


_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 Co1 2.7707(3) . ?
C1 C2 1.395(4) . ?
C1 C11 1.523(4) 3_666 ?
C1 N2 1.340(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.369(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(4) . ?
C5 C6 1.465(4) . ?
C5 N2 1.362(3) . ?
C6 C7 1.383(4) . ?
C6 N1 1.365(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.377(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.376(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(4) . ?
C10 C11 1.535(4) . ?
C10 N1 1.341(4) . ?
C11 C12 1.550(5) . ?
C11 O1 1.420(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
Co1 N1 1.923(2) 3_666 ?
Co1 N1 1.923(2) . ?
Co1 N2 1.925(2) 3_666 ?
Co1 N2 1.925(2) . ?
O1 H1 0.824(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 O2 1.410(6) . ?
O2 H2A 0.821(5) . ?

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
C2 C1 C11 116.6(3) . 3_666 ?
N2 C1 C2 121.0(3) . . ?
N2 C1 C11 121.9(3) . 3_666 ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.5(3) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.4(3) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C6 123.3(3) . . ?
N2 C5 C4 122.3(3) . . ?
N2 C5 C6 114.4(2) . . ?
C7 C6 C5 123.5(3) . . ?
N1 C6 C5 114.2(2) . . ?
N1 C6 C7 122.3(3) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 C6 118.5(3) . . ?
C8 C7 H7 120.8 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.6(3) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.9(3) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C11 117.0(3) . . ?
N1 C10 C9 121.1(3) . . ?
N1 C10 C11 121.5(3) . . ?
C1 C11 C10 119.5(3) 3_666 . ?
C1 C11 C12 106.8(3) 3_666 . ?
C10 C11 C12 106.8(3) . . ?
O1 C11 C1 108.6(3) . 3_666 ?
O1 C11 C10 108.5(3) . . ?
O1 C11 C12 105.8(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
Br1 Co1 Br1 180.0 3_666 . ?
N1 Co1 Br1 91.32(7) 3_666 . ?
N1 Co1 Br1 88.68(7) . . ?
N1 Co1 Br1 88.68(7) 3_666 3_666 ?
N1 Co1 Br1 91.32(7) . 3_666 ?
N1 Co1 N1 180.0 . 3_666 ?
N1 Co1 N2 95.28(10) . 3_666 ?
N1 Co1 N2 95.28(10) 3_666 . ?
N1 Co1 N2 84.72(10) 3_666 3_666 ?
N1 Co1 N2 84.72(10) . . ?
N2 Co1 Br1 87.54(7) 3_666 . ?
N2 Co1 Br1 87.54(7) . 3_666 ?
N2 Co1 Br1 92.46(7) . . ?
N2 Co1 Br1 92.46(7) 3_666 3_666 ?
N2 Co1 N2 180.00(10) 3_666 . ?
C6 N1 Co1 113.11(19) . . ?
C10 N1 C6 118.6(2) . . ?
C10 N1 Co1 128.0(2) . . ?
C1 N2 C5 118.8(2) . . ?
C1 N2 Co1 127.94(19) . . ?
C5 N2 Co1 113.05(19) . . ?
C11 O1 H1 96(5) . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
C13 O2 H2A 107(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.824(5) 1.976(8) 2.799(5) 177(7) . yes
O2 H2A Br1 0.821(5) 2.484(18) 3.287(3) 166(7) . yes


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
