# Electronic Supplementary Material (ESI) for ChemComm.
# 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_fxm-xcr-322dj-136k
_audit_block_doi                 10.5517/ccdc.csd.cc1p26ml
_database_code_depnum_ccdc_archive 'CCDC 1551259'
_audit_update_record             
;
2017-05-20 deposited with the CCDC.
2017-08-07 downloaded from the CCDC.
;
_audit_creation_date             2017-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
'butyl (aR)-3,6-dihydroxy-2-(2-hydroxynaphthalen-1-yl)benzoate'
_chemical_formula_moiety         'C21 H20 O5'
_chemical_formula_sum            'C21 H20 O5'
_chemical_formula_weight         352.37
_chemical_absolute_configuration ad
_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'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.0345(2)
_cell_length_b                   12.6015(4)
_cell_length_c                   9.2114(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.576(3)
_cell_angle_gamma                90
_cell_volume                     889.10(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4923
_cell_measurement_temperature    290.64(10)
_cell_measurement_theta_max      72.5340
_cell_measurement_theta_min      5.0310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8560
_diffrn_reflns_point_group_measured_fraction_full 0.913
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        67.024
_diffrn_reflns_theta_max         67.024
_diffrn_reflns_theta_min         5.036
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.64(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -99.0000  120.0000 74

#__ type_ start__ end____ width___ exp.time_
  3 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000  150.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000   60.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000  120.0000 66

#__ type_ start__ end____ width___ exp.time_
  7 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000  -60.0000 95

#__ type_ start__ end____ width___ exp.time_
  8 omega    9.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000 -150.0000 95

#__ type_ start__ end____ width___ exp.time_
  9 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   38.0000  -90.0000 88

#__ type_ start__ end____ width___ exp.time_
 10 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000  -90.0000 66

#__ type_ start__ end____ width___ exp.time_
 11 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   38.0000   90.0000 88

#__ type_ start__ end____ width___ exp.time_
 12 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
 13 omega   90.00  175.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -30.0000 85

#__ type_ start__ end____ width___ exp.time_
 14 omega   81.00  176.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 95

#__ type_ start__ end____ width___ exp.time_
 15 omega   81.00  176.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 95

#__ type_ start__ end____ width___ exp.time_
 16 omega   81.00  176.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 95

#__ type_ start__ end____ width___ exp.time_
 17 omega   87.00  178.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000    0.0000 91

#__ type_ start__ end____ width___ exp.time_
 18 omega   43.00  134.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  120.0000 91

#__ type_ start__ end____ width___ exp.time_
 19 omega   97.00  123.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   90.00  119.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
 21 omega   87.00  114.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 22 omega   43.00  109.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 66

#__ type_ start__ end____ width___ exp.time_
 23 omega   87.00  117.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
 24 omega  126.00  169.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 43

#__ type_ start__ end____ width___ exp.time_
 25 omega   91.00  117.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   81.00  106.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 27 omega   90.00  116.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 28 omega  129.00  176.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 47

#__ type_ start__ end____ width___ exp.time_
 29 omega   91.00  117.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega  125.00  157.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 32

#__ type_ start__ end____ width___ exp.time_
 31 omega   91.00  117.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 32 omega   81.00  107.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 33 omega   81.00  107.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 34 omega   93.00  121.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
 35 omega   96.00  122.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 36 omega   41.00   96.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 55

#__ type_ start__ end____ width___ exp.time_
 37 omega   89.00  115.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 38 omega   71.00   96.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0390082000
_diffrn_orient_matrix_UB_12      -0.0225974000
_diffrn_orient_matrix_UB_13      -0.1714388000
_diffrn_orient_matrix_UB_21      0.1923862000
_diffrn_orient_matrix_UB_22      0.0224226000
_diffrn_orient_matrix_UB_23      0.0126939000
_diffrn_orient_matrix_UB_31      0.0438995000
_diffrn_orient_matrix_UB_32      -0.1180236000
_diffrn_orient_matrix_UB_33      0.0351019000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.816
_reflns_Friedel_fraction_max     0.816
_reflns_number_gt                2821
_reflns_number_total             2889
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.089
_refine_ls_abs_structure_details 
;
 Flack x determined using 1136 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         2889
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0513
_refine_ls_restrained_S_all      1.042
_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)+(0.0903P)²+0.2308P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1330
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00N(H00a,H00b), C00O(H00e,H00f), C00P(H00g,H00n)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M)
2.c Idealised Me refined as rotating group:
 C00Q(H00o,H00p,H00q)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001), O002(H002), O003(H003)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O001 O 0.2716(3) 0.6408(2) 0.0732(3) 0.0364(6) Uani 1 1 d . . . . .
H001 H 0.2646 0.7047 0.0460 0.055 Uiso 1 1 calc GR . . . .
O002 O 0.0637(3) 0.3785(2) 0.1727(3) 0.0404(7) Uani 1 1 d . . . . .
H002 H 0.0592 0.4344 0.2210 0.061 Uiso 1 1 calc GR . . . .
O003 O 0.6834(3) 0.3322(2) 0.0435(3) 0.0419(7) Uani 1 1 d . . . . .
H003 H 0.7502 0.3845 0.0707 0.063 Uiso 1 1 calc GR . . . .
O004 O 0.6551(3) 0.5681(3) 0.3421(3) 0.0551(9) Uani 1 1 d . . . . .
O005 O 0.7906(4) 0.5061(3) 0.1887(5) 0.0741(13) Uani 1 1 d . . . . .
C006 C 0.3151(4) 0.5382(3) 0.2932(3) 0.0243(7) Uani 1 1 d . . . . .
C007 C 0.2751(4) 0.6346(3) 0.2221(4) 0.0280(7) Uani 1 1 d . . . . .
C008 C 0.5149(4) 0.4331(3) 0.1742(3) 0.0254(7) Uani 1 1 d . . . . .
C009 C 0.3238(4) 0.5285(3) 0.4505(3) 0.0263(7) Uani 1 1 d . . . . .
C00A C 0.3544(4) 0.4463(3) 0.2068(3) 0.0237(7) Uani 1 1 d . . . . .
C00B C 0.5348(4) 0.3486(3) 0.0828(3) 0.0275(7) Uani 1 1 d . . . . .
C00C C 0.4008(4) 0.2755(3) 0.0271(4) 0.0280(7) Uani 1 1 d . . . . .
H00C H 0.4166 0.2174 -0.0330 0.034 Uiso 1 1 calc R . . . .
C00D C 0.2458(4) 0.2875(3) 0.0589(4) 0.0303(7) Uani 1 1 d . . . . .
H00D H 0.1543 0.2377 0.0204 0.036 Uiso 1 1 calc R . . . .
C00E C 0.2218(4) 0.3720(3) 0.1471(4) 0.0290(7) Uani 1 1 d . . . . .
C00F C 0.6667(4) 0.5049(3) 0.2371(4) 0.0291(7) Uani 1 1 d . . . . .
C00G C 0.2916(4) 0.6197(3) 0.5294(4) 0.0296(7) Uani 1 1 d . . . . .
C00H C 0.2419(5) 0.7246(3) 0.3003(4) 0.0333(8) Uani 1 1 d . . . . .
H00H H 0.2132 0.7906 0.2490 0.040 Uiso 1 1 calc R . . . .
C00I C 0.3704(5) 0.4325(3) 0.5318(4) 0.0323(8) Uani 1 1 d . . . . .
H00I H 0.3935 0.3713 0.4809 0.039 Uiso 1 1 calc R . . . .
C00J C 0.3028(4) 0.6089(3) 0.6856(4) 0.0357(8) Uani 1 1 d . . . . .
H00J H 0.2785 0.6686 0.7388 0.043 Uiso 1 1 calc R . . . .
C00K C 0.2513(5) 0.7160(3) 0.4508(4) 0.0341(8) Uani 1 1 d . . . . .
H00K H 0.2300 0.7770 0.5032 0.041 Uiso 1 1 calc R . . . .
C00L C 0.3828(5) 0.4266(4) 0.6838(4) 0.0417(9) Uani 1 1 d . . . . .
H00L H 0.4156 0.3617 0.7372 0.050 Uiso 1 1 calc R . . . .
C00M C 0.3471(5) 0.5163(4) 0.7603(4) 0.0423(10) Uani 1 1 d . . . . .
H00M H 0.3542 0.5116 0.8649 0.051 Uiso 1 1 calc R . . . .
C00N C 0.8178(5) 0.6307(3) 0.5886(5) 0.0422(9) Uani 1 1 d . . . . .
H00A H 0.9114 0.6798 0.6448 0.051 Uiso 1 1 calc R . . . .
H00B H 0.7067 0.6563 0.6017 0.051 Uiso 1 1 calc R . . . .
C00O C 0.8561(5) 0.5219(4) 0.6571(5) 0.0535(12) Uani 1 1 d . . . . .
H00E H 0.9639 0.4946 0.6394 0.064 Uiso 1 1 calc R . . . .
H00F H 0.7592 0.4736 0.6052 0.064 Uiso 1 1 calc R . . . .
C00P C 0.8042(5) 0.6344(4) 0.4219(5) 0.0527(12) Uani 1 1 d . . . . .
H00G H 0.7860 0.7083 0.3838 0.063 Uiso 1 1 calc R . . . .
H00N H 0.9126 0.6069 0.4055 0.063 Uiso 1 1 calc R . . . .
C00Q C 0.8792(8) 0.5212(5) 0.8269(6) 0.0696(15) Uani 1 1 d . . . . .
H00O H 0.7698 0.5430 0.8446 0.104 Uiso 1 1 calc GR . . . .
H00P H 0.9723 0.5707 0.8785 0.104 Uiso 1 1 calc GR . . . .
H00Q H 0.9102 0.4495 0.8672 0.104 Uiso 1 1 calc GR . . . .


_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
O001 H001 0.8400 . ?
O001 C007 1.366(4) . ?
O002 H002 0.8400 . ?
O002 C00E 1.363(4) . ?
O003 H003 0.8400 . ?
O003 C00B 1.364(4) . ?
O004 C00F 1.277(4) . ?
O004 C00P 1.463(4) . ?
O005 C00F 1.208(4) . ?
C006 C007 1.371(5) . ?
C006 C009 1.435(4) . ?
C006 C00A 1.492(4) . ?
C007 C00H 1.411(5) . ?
C008 C00A 1.419(4) . ?
C008 C00B 1.397(4) . ?
C008 C00F 1.488(4) . ?
C009 C00G 1.424(5) . ?
C009 C00I 1.412(5) . ?
C00A C00E 1.399(4) . ?
C00B C00C 1.392(5) . ?
C00C H00C 0.9500 . ?
C00C C00D 1.371(5) . ?
C00D H00D 0.9500 . ?
C00D C00E 1.388(5) . ?
C00G C00J 1.421(5) . ?
C00G C00K 1.401(5) . ?
C00H H00H 0.9500 . ?
C00H C00K 1.369(5) . ?
C00I H00I 0.9500 . ?
C00I C00L 1.375(5) . ?
C00J H00J 0.9500 . ?
C00J C00M 1.346(6) . ?
C00K H00K 0.9500 . ?
C00L H00L 0.9500 . ?
C00L C00M 1.408(6) . ?
C00M H00M 0.9500 . ?
C00N H00A 0.9900 . ?
C00N H00B 0.9900 . ?
C00N C00O 1.502(7) . ?
C00N C00P 1.507(6) . ?
C00O H00E 0.9900 . ?
C00O H00F 0.9900 . ?
C00O C00Q 1.519(7) . ?
C00P H00G 0.9900 . ?
C00P H00N 0.9900 . ?
C00Q H00O 0.9800 . ?
C00Q H00P 0.9800 . ?
C00Q H00Q 0.9800 . ?

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
C007 O001 H001 109.5 . . ?
C00E O002 H002 109.5 . . ?
C00B O003 H003 109.5 . . ?
C00F O004 C00P 120.0(3) . . ?
C007 C006 C009 119.4(3) . . ?
C007 C006 C00A 119.3(3) . . ?
C009 C006 C00A 121.3(3) . . ?
O001 C007 C006 117.4(3) . . ?
O001 C007 C00H 121.2(3) . . ?
C006 C007 C00H 121.4(3) . . ?
C00A C008 C00F 122.5(3) . . ?
C00B C008 C00A 119.6(3) . . ?
C00B C008 C00F 118.0(3) . . ?
C00G C009 C006 119.1(3) . . ?
C00I C009 C006 122.2(3) . . ?
C00I C009 C00G 118.7(3) . . ?
C008 C00A C006 123.8(3) . . ?
C00E C00A C006 118.0(3) . . ?
C00E C00A C008 118.1(3) . . ?
O003 C00B C008 123.0(3) . . ?
O003 C00B C00C 116.3(3) . . ?
C00C C00B C008 120.7(3) . . ?
C00B C00C H00C 120.0 . . ?
C00D C00C C00B 120.0(3) . . ?
C00D C00C H00C 120.0 . . ?
C00C C00D H00D 119.8 . . ?
C00C C00D C00E 120.3(3) . . ?
C00E C00D H00D 119.8 . . ?
O002 C00E C00A 122.1(3) . . ?
O002 C00E C00D 116.6(3) . . ?
C00D C00E C00A 121.3(3) . . ?
O004 C00F C008 115.8(3) . . ?
O005 C00F O004 121.9(3) . . ?
O005 C00F C008 122.3(3) . . ?
C00J C00G C009 118.3(3) . . ?
C00K C00G C009 119.0(3) . . ?
C00K C00G C00J 122.7(3) . . ?
C007 C00H H00H 120.3 . . ?
C00K C00H C007 119.5(3) . . ?
C00K C00H H00H 120.3 . . ?
C009 C00I H00I 119.6 . . ?
C00L C00I C009 120.9(3) . . ?
C00L C00I H00I 119.6 . . ?
C00G C00J H00J 119.1 . . ?
C00M C00J C00G 121.8(3) . . ?
C00M C00J H00J 119.1 . . ?
C00G C00K H00K 119.2 . . ?
C00H C00K C00G 121.7(3) . . ?
C00H C00K H00K 119.2 . . ?
C00I C00L H00L 119.9 . . ?
C00I C00L C00M 120.2(4) . . ?
C00M C00L H00L 119.9 . . ?
C00J C00M C00L 120.2(3) . . ?
C00J C00M H00M 119.9 . . ?
C00L C00M H00M 119.9 . . ?
H00A C00N H00B 107.7 . . ?
C00O C00N H00A 108.9 . . ?
C00O C00N H00B 108.9 . . ?
C00O C00N C00P 113.5(4) . . ?
C00P C00N H00A 108.9 . . ?
C00P C00N H00B 108.9 . . ?
C00N C00O H00E 109.1 . . ?
C00N C00O H00F 109.1 . . ?
C00N C00O C00Q 112.6(4) . . ?
H00E C00O H00F 107.8 . . ?
C00Q C00O H00E 109.1 . . ?
C00Q C00O H00F 109.1 . . ?
O004 C00P C00N 106.9(3) . . ?
O004 C00P H00G 110.3 . . ?
O004 C00P H00N 110.3 . . ?
C00N C00P H00G 110.3 . . ?
C00N C00P H00N 110.3 . . ?
H00G C00P H00N 108.6 . . ?
C00O C00Q H00O 109.5 . . ?
C00O C00Q H00P 109.5 . . ?
C00O C00Q H00Q 109.5 . . ?
H00O C00Q H00P 109.5 . . ?
H00O C00Q H00Q 109.5 . . ?
H00P C00Q H00Q 109.5 . . ?

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
O001 C007 C00H C00K -178.2(3) . . . . ?
O003 C00B C00C C00D -178.7(3) . . . . ?
C006 C007 C00H C00K 0.6(5) . . . . ?
C006 C009 C00G C00J -179.3(3) . . . . ?
C006 C009 C00G C00K 0.4(4) . . . . ?
C006 C009 C00I C00L 178.0(3) . . . . ?
C006 C00A C00E O002 -3.6(5) . . . . ?
C006 C00A C00E C00D 176.7(3) . . . . ?
C007 C006 C009 C00G -0.4(4) . . . . ?
C007 C006 C009 C00I -177.7(3) . . . . ?
C007 C006 C00A C008 76.2(4) . . . . ?
C007 C006 C00A C00E -100.0(3) . . . . ?
C007 C00H C00K C00G -0.6(5) . . . . ?
C008 C00A C00E O002 179.9(3) . . . . ?
C008 C00A C00E C00D 0.2(5) . . . . ?
C008 C00B C00C C00D 1.5(5) . . . . ?
C009 C006 C007 O001 178.7(3) . . . . ?
C009 C006 C007 C00H -0.1(4) . . . . ?
C009 C006 C00A C008 -101.7(3) . . . . ?
C009 C006 C00A C00E 82.0(4) . . . . ?
C009 C00G C00J C00M 1.7(5) . . . . ?
C009 C00G C00K C00H 0.1(5) . . . . ?
C009 C00I C00L C00M 0.7(6) . . . . ?
C00A C006 C007 O001 0.7(4) . . . . ?
C00A C006 C007 C00H -178.1(3) . . . . ?
C00A C006 C009 C00G 177.6(3) . . . . ?
C00A C006 C009 C00I 0.3(4) . . . . ?
C00A C008 C00B O003 178.4(3) . . . . ?
C00A C008 C00B C00C -1.9(4) . . . . ?
C00A C008 C00F O004 11.3(5) . . . . ?
C00A C008 C00F O005 -166.3(4) . . . . ?
C00B C008 C00A C006 -175.2(3) . . . . ?
C00B C008 C00A C00E 1.0(4) . . . . ?
C00B C008 C00F O004 -167.2(3) . . . . ?
C00B C008 C00F O005 15.2(5) . . . . ?
C00B C00C C00D C00E -0.3(5) . . . . ?
C00C C00D C00E O002 179.7(3) . . . . ?
C00C C00D C00E C00A -0.6(5) . . . . ?
C00F O004 C00P C00N -137.1(4) . . . . ?
C00F C008 C00A C006 6.3(5) . . . . ?
C00F C008 C00A C00E -177.5(3) . . . . ?
C00F C008 C00B O003 -3.1(5) . . . . ?
C00F C008 C00B C00C 176.7(3) . . . . ?
C00G C009 C00I C00L 0.7(5) . . . . ?
C00G C00J C00M C00L -0.3(5) . . . . ?
C00I C009 C00G C00J -1.8(4) . . . . ?
C00I C009 C00G C00K 177.8(3) . . . . ?
C00I C00L C00M C00J -0.9(6) . . . . ?
C00J C00G C00K C00H 179.7(3) . . . . ?
C00K C00G C00J C00M -177.9(3) . . . . ?
C00O C00N C00P O004 63.4(4) . . . . ?
C00P O004 C00F O005 -8.5(6) . . . . ?
C00P O004 C00F C008 173.9(4) . . . . ?
C00P C00N C00O C00Q 176.8(3) . . . . ?

_olex2_date_sample_data_collection 2017-03-22
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/THF'
_chemical_properties_physical    
', Air-sensitive,Heat-sensitive,Oxygen-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_1
_audit_block_doi                 10.5517/ccdc.csd.cc1p26nm
_database_code_depnum_ccdc_archive 'CCDC 1551260'
_audit_update_record             
;
2017-05-20 deposited with the CCDC.
2017-08-07 downloaded from the CCDC.
;
_audit_creation_date             2017-04-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        'L-RaPr2/Co(ClO4)2?6H2O complex'
_chemical_formula_moiety         'C51 H80 Co N4 O6, 2(Cl O4)'
_chemical_formula_sum            'C51 H80 Cl2 Co N4 O14'
_chemical_formula_weight         1103.02
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C191
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.6288(8)
_cell_length_b                   16.6036(7)
_cell_length_c                   13.9577(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.375(5)
_cell_angle_gamma                90
_cell_volume                     2926.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7066
_cell_measurement_temperature    143.00(10)
_cell_measurement_theta_max      24.1090
_cell_measurement_theta_min      3.2540
_shelx_estimated_absorpt_T_max   0.897
_shelx_estimated_absorpt_T_min   0.859
_exptl_absorpt_coefficient_mu    0.447
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1174
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28110
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.936
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      143.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  20.00   1.00    7.50    --  -14.97 -99.00  90.00   28
  2  ω    -79.00  -8.00   1.00    7.50    --  -14.97 -57.00-150.00   71
  3  ω    -39.00  22.00   1.00    7.50    --   16.84 -57.00  90.00   61
  4  ω    -72.00   8.00   1.00    7.50    --  -14.81 -77.00 120.00   80
  5  ω    -50.00  13.00   1.00    7.50    --   16.53 -57.00-180.00   63
  6  ω      3.00  55.00   1.00    7.50    --   16.53 -99.00 -30.00   52
  7  ω    -21.00   8.00   1.00    7.50    --   16.53 -99.00 -90.00   29
  8  ω     12.00  55.00   1.00    7.50    --   16.53 -99.00   0.00   43
  9  ω     22.00  57.00   1.00    7.50    --   16.53-101.00  37.07   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0458576000
_diffrn_orient_matrix_UB_12      0.0037294000
_diffrn_orient_matrix_UB_13      -0.0293271000
_diffrn_orient_matrix_UB_21      -0.0322604000
_diffrn_orient_matrix_UB_22      -0.0010089000
_diffrn_orient_matrix_UB_23      0.0413652000
_diffrn_orient_matrix_UB_31      0.0032157000
_diffrn_orient_matrix_UB_32      0.0425425000
_diffrn_orient_matrix_UB_33      0.0035006000
_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'
_reflns_Friedel_coverage         0.929
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                8292
_reflns_number_total             11959
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.938
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 2871 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.020(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     639
_refine_ls_number_reflns         11959
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0698
_refine_ls_restrained_S_all      0.990
_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)+(0.1236P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1768
_refine_ls_wR_factor_ref         0.1959
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl2-O14
 1.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C23) = Uanis(C22) = Uanis(C49) = Uanis(C50)
4.a Ternary CH refined with riding coordinates:
 C1(H1), C5(H5), C7(H7), C15(H15), C18(H18), C25(H25), C29(H29), C31(H31),
 C42(H42), C45(H45)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C21(H21A,H21B), C22(H22A,
 H22B), C23(H23A,H23B), C24(H24A,H24B), C26(H26A,H26B), C27(H27A,H27B),
 C28(H28A,H28B), C30(H30A,H30B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B),
  C48(H48A,H48B), C49(H49A,H49B), C50(H50A,H50B), C51(H51A,H51B)
4.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), C11(H11), C12(H12), C13(H13), C38(H38), C39(H39), C40(H40)
4.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C46(H46A,H46B,H46C), C47(H47A,
 H47B,H47C)
;
_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
Co1 Co 0.26758(6) 0.51994(4) 0.73428(5) 0.0462(2) Uani 1 1 d . . . . .
O1 O 0.2072(3) 0.4568(2) 0.8430(3) 0.0461(10) Uani 1 1 d . . . . .
O2 O 0.1922(4) 0.4394(3) 0.6395(3) 0.0562(11) Uani 1 1 d . . . . .
O5 O 0.4087(3) 0.4645(2) 0.7245(3) 0.0462(9) Uani 1 1 d . . . . .
O4 O 0.3430(4) 0.6039(3) 0.8251(3) 0.0563(11) Uani 1 1 d . . . . .
N1 N 0.1905(4) 0.3733(3) 0.8342(4) 0.0478(12) Uani 1 1 d . . . . .
N2 N 0.0984(5) 0.3339(4) 0.5889(4) 0.0635(16) Uani 1 1 d . . . . .
H2 H 0.0564 0.2937 0.6043 0.076 Uiso 1 1 calc R . . . .
O3 O 0.3058(5) 0.5836(3) 0.6081(4) 0.0802(16) Uani 1 1 d . . . . .
N3 N 0.4784(4) 0.4630(3) 0.8012(4) 0.0482(12) Uani 1 1 d . . . . .
N4 N 0.4745(5) 0.6694(3) 0.9016(4) 0.0587(14) Uani 1 1 d . . . . .
H4 H 0.5433 0.6730 0.9110 0.070 Uiso 1 1 calc R . . . .
O6 O 0.1367(5) 0.6017(3) 0.7397(4) 0.0769(16) Uani 1 1 d . . . . .
C1 C 0.1321(6) 0.3442(4) 0.9244(5) 0.0608(17) Uani 1 1 d . . . . .
H1 H 0.1358 0.2842 0.9289 0.073 Uiso 1 1 calc R . . . .
C2 C 0.1688(7) 0.3815(5) 1.0176(5) 0.0672(19) Uani 1 1 d . . . . .
H2A H 0.2227 0.4237 1.0062 0.081 Uiso 1 1 calc R . . . .
H2B H 0.1990 0.3403 1.0612 0.081 Uiso 1 1 calc R . . . .
C3 C 0.0680(9) 0.4177(7) 1.0588(7) 0.100(3) Uani 1 1 d . . . . .
H3A H 0.0335 0.3784 1.1019 0.120 Uiso 1 1 calc R . . . .
H3B H 0.0852 0.4666 1.0964 0.120 Uiso 1 1 calc R . . . .
C4 C -0.0025(8) 0.4380(8) 0.9808(6) 0.096(3) Uani 1 1 d . . . . .
H4A H 0.0151 0.4914 0.9537 0.115 Uiso 1 1 calc R . . . .
H4B H -0.0771 0.4383 1.0021 0.115 Uiso 1 1 calc R . . . .
C5 C 0.0165(7) 0.3711(5) 0.9077(5) 0.069(2) Uani 1 1 d . . . . .
H5 H -0.0320 0.3250 0.9214 0.082 Uiso 1 1 calc R . . . .
C6 C 0.0083(6) 0.3930(5) 0.8021(5) 0.067(2) Uani 1 1 d . . . . .
H6A H -0.0568 0.3702 0.7729 0.081 Uiso 1 1 calc R . . . .
H6B H 0.0081 0.4522 0.7931 0.081 Uiso 1 1 calc R . . . .
C7 C 0.1061(6) 0.3556(4) 0.7592(5) 0.0540(16) Uani 1 1 d . . . . .
H7 H 0.0951 0.2960 0.7583 0.065 Uiso 1 1 calc R . . . .
C8 C 0.1362(5) 0.3807(4) 0.6587(4) 0.0481(14) Uani 1 1 d . . . . .
C9 C 0.1229(7) 0.3462(5) 0.4899(5) 0.064(2) Uani 1 1 d . . . . .
C10 C 0.0533(8) 0.3905(6) 0.4322(5) 0.081(3) Uani 1 1 d . . . . .
C11 C 0.0814(9) 0.4012(8) 0.3355(7) 0.097(3) Uani 1 1 d . . . . .
H11 H 0.0348 0.4294 0.2935 0.116 Uiso 1 1 calc R . . . .
C12 C 0.1714(10) 0.3726(9) 0.3025(7) 0.110(4) Uani 1 1 d . . . . .
H12 H 0.1920 0.3851 0.2389 0.132 Uiso 1 1 calc R . . . .
C13 C 0.2350(10) 0.3259(9) 0.3575(8) 0.108(4) Uani 1 1 d . . . . .
H13 H 0.2955 0.3018 0.3294 0.129 Uiso 1 1 calc R . . . .
C14 C 0.2146(7) 0.3117(6) 0.4545(6) 0.078(2) Uani 1 1 d . . . . .
C15 C -0.0498(8) 0.4240(6) 0.4691(6) 0.083(2) Uani 1 1 d . . . . .
H15 H -0.0494 0.4198 0.5406 0.100 Uiso 1 1 calc R . . . .
C16 C -0.0707(16) 0.5089(11) 0.4425(13) 0.172(7) Uani 1 1 d . . . . .
H16A H -0.0299 0.5447 0.4847 0.258 Uiso 1 1 calc GR . . . .
H16B H -0.1464 0.5204 0.4494 0.258 Uiso 1 1 calc GR . . . .
H16C H -0.0497 0.5179 0.3759 0.258 Uiso 1 1 calc GR . . . .
C17 C -0.1424(9) 0.3750(11) 0.4302(14) 0.165(8) Uani 1 1 d . . . . .
H17A H -0.1471 0.3819 0.3606 0.247 Uiso 1 1 calc GR . . . .
H17B H -0.2082 0.3937 0.4598 0.247 Uiso 1 1 calc GR . . . .
H17C H -0.1314 0.3180 0.4453 0.247 Uiso 1 1 calc GR . . . .
C18 C 0.2828(11) 0.2597(8) 0.5167(9) 0.110(4) Uani 1 1 d . . . . .
H18 H 0.2642 0.2740 0.5842 0.132 Uiso 1 1 calc R . . . .
C19 C 0.3942(15) 0.2741(15) 0.5085(19) 0.229(11) Uani 1 1 d . . . . .
H19A H 0.4071 0.3113 0.4554 0.343 Uiso 1 1 calc GR . . . .
H19B H 0.4307 0.2231 0.4963 0.343 Uiso 1 1 calc GR . . . .
H19C H 0.4211 0.2977 0.5683 0.343 Uiso 1 1 calc GR . . . .
C20 C 0.2566(17) 0.1746(10) 0.506(2) 0.235(13) Uani 1 1 d . . . . .
H20A H 0.2577 0.1485 0.5688 0.353 Uiso 1 1 calc GR . . . .
H20B H 0.3087 0.1488 0.4641 0.353 Uiso 1 1 calc GR . . . .
H20C H 0.1859 0.1694 0.4773 0.353 Uiso 1 1 calc GR . . . .
C21 C 0.3203(11) 0.5401(9) 0.5169(12) 0.140(6) Uani 1 1 d . . . . .
H21A H 0.2517 0.5278 0.4854 0.168 Uiso 1 1 calc R . . . .
H21B H 0.3609 0.4896 0.5260 0.168 Uiso 1 1 calc R . . . .
C22 C 0.3826(16) 0.6022(12) 0.4619(16) 0.184(4) Uani 1 1 d . . . . .
H22A H 0.3704 0.5964 0.3921 0.221 Uiso 1 1 calc R . . . .
H22B H 0.4594 0.5970 0.4753 0.221 Uiso 1 1 calc R . . . .
C23 C 0.3405(17) 0.6835(13) 0.4980(14) 0.184(4) Uani 1 1 d . . . . .
H23A H 0.3950 0.7262 0.4939 0.221 Uiso 1 1 calc R . . . .
H23B H 0.2766 0.7006 0.4619 0.221 Uiso 1 1 calc R . . . .
C24 C 0.3154(18) 0.6641(10) 0.5984(12) 0.173(7) Uani 1 1 d . . . . .
H24A H 0.3724 0.6841 0.6412 0.208 Uiso 1 1 calc R . . . .
H24B H 0.2484 0.6907 0.6169 0.208 Uiso 1 1 calc R . . . .
C25 C 0.5811(6) 0.4184(5) 0.7698(6) 0.070(2) Uani 1 1 d . . . . .
H25 H 0.6147 0.3921 0.8268 0.084 Uiso 1 1 calc R . . . .
C26 C 0.5654(7) 0.3570(4) 0.6915(6) 0.072(2) Uani 1 1 d . . . . .
H26A H 0.4900 0.3411 0.6860 0.086 Uiso 1 1 calc R . . . .
H26B H 0.6085 0.3082 0.7038 0.086 Uiso 1 1 calc R . . . .
C27 C 0.6017(10) 0.3994(7) 0.6018(7) 0.104(3) Uani 1 1 d . . . . .
H27A H 0.6312 0.3602 0.5557 0.125 Uiso 1 1 calc R . . . .
H27B H 0.5416 0.4277 0.5707 0.125 Uiso 1 1 calc R . . . .
C28 C 0.6831(12) 0.4571(7) 0.6316(11) 0.138(6) Uani 1 1 d . . . . .
H28A H 0.6845 0.5037 0.5874 0.166 Uiso 1 1 calc R . . . .
H28B H 0.7538 0.4313 0.6318 0.166 Uiso 1 1 calc R . . . .
C29 C 0.6541(9) 0.4842(6) 0.7318(8) 0.095(3) Uani 1 1 d . . . . .
H29 H 0.7193 0.4878 0.7727 0.114 Uiso 1 1 calc R . . . .
C30 C 0.5894(7) 0.5653(5) 0.7385(7) 0.076(2) Uani 1 1 d . . . . .
H30A H 0.6361 0.6121 0.7508 0.091 Uiso 1 1 calc R . . . .
H30B H 0.5467 0.5751 0.6799 0.091 Uiso 1 1 calc R . . . .
C31 C 0.5207(6) 0.5463(4) 0.8237(5) 0.0543(16) Uani 1 1 d . . . . .
H31 H 0.5688 0.5409 0.8806 0.065 Uiso 1 1 calc R . . . .
C32 C 0.4370(6) 0.6075(4) 0.8495(5) 0.0481(15) Uani 1 1 d . . . . .
C33 C 0.4297(6) 0.4276(4) 0.8901(5) 0.0550(16) Uani 1 1 d . . . . .
H33A H 0.3723 0.4639 0.9114 0.066 Uiso 1 1 calc R . . . .
H33B H 0.4843 0.4267 0.9413 0.066 Uiso 1 1 calc R . . . .
C34 C 0.3842(7) 0.3428(4) 0.8798(5) 0.0633(18) Uani 1 1 d . . . . .
H34A H 0.3622 0.3246 0.9442 0.076 Uiso 1 1 calc R . . . .
H34B H 0.4424 0.3069 0.8593 0.076 Uiso 1 1 calc R . . . .
C35 C 0.2904(6) 0.3292(3) 0.8111(5) 0.0529(16) Uani 1 1 d . . . . .
H35A H 0.3126 0.3450 0.7459 0.063 Uiso 1 1 calc R . . . .
H35B H 0.2745 0.2708 0.8095 0.063 Uiso 1 1 calc R . . . .
C36 C 0.4074(5) 0.7296(4) 0.9423(5) 0.0576(17) Uani 1 1 d . . . . .
C37 C 0.3941(6) 0.8036(4) 0.8962(6) 0.0649(19) Uani 1 1 d . . . . .
C38 C 0.3290(8) 0.8603(5) 0.9399(8) 0.081(3) Uani 1 1 d . . . . .
H38 H 0.3202 0.9123 0.9127 0.097 Uiso 1 1 calc R . . . .
C39 C 0.2786(8) 0.8402(6) 1.0212(8) 0.087(3) Uani 1 1 d . . . . .
H39 H 0.2334 0.8794 1.0490 0.104 Uiso 1 1 calc R . . . .
C40 C 0.2877(7) 0.7678(6) 1.0667(8) 0.089(3) Uani 1 1 d . . . . .
H40 H 0.2490 0.7565 1.1232 0.106 Uiso 1 1 calc R . . . .
C41 C 0.3563(7) 0.7110(5) 1.0269(7) 0.074(2) Uani 1 1 d . . . . .
C42 C 0.4536(9) 0.8242(5) 0.8073(7) 0.090(3) Uani 1 1 d . . . . .
H42 H 0.4873 0.7738 0.7830 0.108 Uiso 1 1 calc R . . . .
C43 C 0.3806(16) 0.8575(15) 0.7270(10) 0.193(9) Uani 1 1 d . . . . .
H43A H 0.3578 0.8132 0.6854 0.290 Uiso 1 1 calc GR . . . .
H43B H 0.4194 0.8973 0.6892 0.290 Uiso 1 1 calc GR . . . .
H43C H 0.3184 0.8830 0.7557 0.290 Uiso 1 1 calc GR . . . .
C44 C 0.5402(12) 0.8848(10) 0.8256(11) 0.144(6) Uani 1 1 d . . . . .
H44A H 0.5117 0.9302 0.8621 0.215 Uiso 1 1 calc GR . . . .
H44B H 0.5676 0.9043 0.7643 0.215 Uiso 1 1 calc GR . . . .
H44C H 0.5975 0.8593 0.8622 0.215 Uiso 1 1 calc GR . . . .
C45 C 0.3720(9) 0.6301(5) 1.0790(7) 0.094(3) Uani 1 1 d . . . . .
H45 H 0.4200 0.5962 1.0391 0.113 Uiso 1 1 calc R . . . .
C46 C 0.2636(14) 0.5855(8) 1.0867(13) 0.163(7) Uani 1 1 d . . . . .
H46A H 0.2136 0.6191 1.1222 0.245 Uiso 1 1 calc GR . . . .
H46B H 0.2737 0.5343 1.1204 0.245 Uiso 1 1 calc GR . . . .
H46C H 0.2355 0.5752 1.0222 0.245 Uiso 1 1 calc GR . . . .
C47 C 0.4232(14) 0.6400(7) 1.1771(10) 0.135(5) Uani 1 1 d . . . . .
H47A H 0.5003 0.6426 1.1701 0.203 Uiso 1 1 calc GR . . . .
H47B H 0.4047 0.5940 1.2176 0.203 Uiso 1 1 calc GR . . . .
H47C H 0.3978 0.6898 1.2067 0.203 Uiso 1 1 calc GR . . . .
C48 C 0.0567(12) 0.6088(9) 0.6631(11) 0.143(6) Uani 1 1 d . . . . .
H48A H 0.0260 0.5555 0.6477 0.172 Uiso 1 1 calc R . . . .
H48B H 0.0885 0.6315 0.6043 0.172 Uiso 1 1 calc R . . . .
C49 C -0.0252(16) 0.6635(14) 0.7012(16) 0.184(4) Uani 1 1 d . . . . .
H49A H -0.0393 0.7077 0.6553 0.221 Uiso 1 1 calc R . . . .
H49B H -0.0921 0.6337 0.7118 0.221 Uiso 1 1 calc R . . . .
C50 C 0.0153(17) 0.6962(13) 0.7928(16) 0.184(4) Uani 1 1 d . . . . .
H50A H -0.0407 0.6944 0.8420 0.221 Uiso 1 1 calc R . . . .
H50B H 0.0375 0.7529 0.7843 0.221 Uiso 1 1 calc R . . . .
C51 C 0.1067(9) 0.6466(7) 0.8235(8) 0.100(3) Uani 1 1 d . . . . .
H51A H 0.1658 0.6812 0.8457 0.119 Uiso 1 1 calc R . . . .
H51B H 0.0865 0.6099 0.8761 0.119 Uiso 1 1 calc R . . . .
Cl1 Cl -0.1048(4) 0.1876(2) 0.6809(5) 0.197(3) Uani 1 1 d . . . . .
O10 O -0.0437(12) 0.1996(7) 0.6033(13) 0.226(8) Uani 1 1 d . . . . .
O7 O -0.027(3) 0.1961(15) 0.7693(17) 0.40(2) Uani 1 1 d . . . . .
O9 O -0.1679(11) 0.2567(8) 0.6919(11) 0.187(5) Uani 1 1 d . . . . .
O8 O -0.1535(9) 0.1136(6) 0.6791(9) 0.163(4) Uani 1 1 d . . . . .
Cl2 Cl 0.7513(3) 0.6223(2) 0.9851(4) 0.169(2) Uani 1 1 d D . . . .
O12 O 0.7669(19) 0.5617(11) 0.928(2) 0.324(17) Uani 1 1 d . . . . .
O11 O 0.8449(10) 0.6458(7) 1.0242(15) 0.263(10) Uani 1 1 d . . . . .
O13 O 0.6967(10) 0.6831(6) 0.9496(14) 0.223(8) Uani 1 1 d . . . . .
O14 O 0.673(2) 0.572(2) 1.027(2) 0.348(17) 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
Co1 O1 2.000(4) . ?
Co1 O2 2.104(4) . ?
Co1 O5 2.011(4) . ?
Co1 O4 2.107(4) . ?
Co1 O3 2.112(6) . ?
Co1 O6 2.141(5) . ?
O1 N1 1.408(6) . ?
O2 C8 1.235(8) . ?
O5 N3 1.382(7) . ?
O4 C32 1.234(8) . ?
N1 C1 1.541(9) . ?
N1 C7 1.517(9) . ?
N1 C35 1.496(8) . ?
N2 H2 0.8800 . ?
N2 C8 1.332(8) . ?
N2 C9 1.432(9) . ?
O3 C21 1.476(18) . ?
O3 C24 1.348(16) . ?
N3 C25 1.559(9) . ?
N3 C31 1.515(9) . ?
N3 C33 1.507(9) . ?
N4 H4 0.8800 . ?
N4 C32 1.343(8) . ?
N4 C36 1.430(9) . ?
O6 C48 1.472(13) . ?
O6 C51 1.439(12) . ?
C1 H1 1.0000 . ?
C1 C2 1.511(10) . ?
C1 C5 1.543(12) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.524(13) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.442(14) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.527(12) . ?
C5 H5 1.0000 . ?
C5 C6 1.521(11) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.510(11) . ?
C7 H7 1.0000 . ?
C7 C8 1.514(9) . ?
C9 C10 1.397(13) . ?
C9 C14 1.386(12) . ?
C10 C11 1.409(12) . ?
C10 C15 1.510(14) . ?
C11 H11 0.9500 . ?
C11 C12 1.318(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.352(17) . ?
C13 H13 0.9500 . ?
C13 C14 1.400(14) . ?
C14 C18 1.495(17) . ?
C15 H15 1.0000 . ?
C15 C16 1.481(19) . ?
C15 C17 1.521(15) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18 1.0000 . ?
C18 C19 1.43(2) . ?
C18 C20 1.46(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.51(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.54(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.47(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25 1.0000 . ?
C25 C26 1.508(11) . ?
C25 C29 1.528(13) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.510(13) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.464(17) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.516(15) . ?
C29 H29 1.0000 . ?
C29 C30 1.578(14) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.511(11) . ?
C31 H31 1.0000 . ?
C31 C32 1.511(9) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.527(11) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 C35 1.536(11) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.397(11) . ?
C36 C41 1.384(12) . ?
C37 C38 1.394(12) . ?
C37 C42 1.494(13) . ?
C38 H38 0.9500 . ?
C38 C39 1.346(14) . ?
C39 H39 0.9500 . ?
C39 C40 1.364(15) . ?
C40 H40 0.9500 . ?
C40 C41 1.398(12) . ?
C41 C45 1.539(14) . ?
C42 H42 1.0000 . ?
C42 C43 1.548(16) . ?
C42 C44 1.506(16) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45 1.0000 . ?
C45 C46 1.561(17) . ?
C45 C47 1.519(18) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C48 C49 1.48(2) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C49 C50 1.48(3) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C50 C51 1.48(2) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
Cl1 O10 1.348(12) . ?
Cl1 O7 1.58(2) . ?
Cl1 O9 1.405(13) . ?
Cl1 O8 1.374(9) . ?
Cl2 O12 1.30(2) . ?
Cl2 O11 1.356(10) . ?
Cl2 O13 1.318(12) . ?
Cl2 O14 1.42(2) . ?

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
O1 Co1 O2 88.34(17) . . ?
O1 Co1 O5 98.85(17) . . ?
O1 Co1 O4 93.59(18) . . ?
O1 Co1 O3 170.2(2) . . ?
O1 Co1 O6 90.4(2) . . ?
O2 Co1 O4 177.87(19) . . ?
O2 Co1 O3 84.2(2) . . ?
O2 Co1 O6 94.6(2) . . ?
O5 Co1 O2 93.64(18) . . ?
O5 Co1 O4 86.94(17) . . ?
O5 Co1 O3 88.0(2) . . ?
O5 Co1 O6 167.8(2) . . ?
O4 Co1 O3 93.8(2) . . ?
O4 Co1 O6 84.5(2) . . ?
O3 Co1 O6 83.9(2) . . ?
N1 O1 Co1 120.5(3) . . ?
C8 O2 Co1 128.5(4) . . ?
N3 O5 Co1 121.1(3) . . ?
C32 O4 Co1 128.9(4) . . ?
O1 N1 C1 108.0(4) . . ?
O1 N1 C7 110.8(5) . . ?
O1 N1 C35 112.0(5) . . ?
C7 N1 C1 99.6(5) . . ?
C35 N1 C1 115.5(5) . . ?
C35 N1 C7 110.2(5) . . ?
C8 N2 H2 118.5 . . ?
C8 N2 C9 123.0(6) . . ?
C9 N2 H2 118.5 . . ?
C21 O3 Co1 120.3(6) . . ?
C24 O3 Co1 126.9(9) . . ?
C24 O3 C21 112.8(10) . . ?
O5 N3 C25 108.5(5) . . ?
O5 N3 C31 111.5(5) . . ?
O5 N3 C33 112.5(5) . . ?
C31 N3 C25 101.5(5) . . ?
C33 N3 C25 113.0(5) . . ?
C33 N3 C31 109.3(5) . . ?
C32 N4 H4 118.6 . . ?
C32 N4 C36 122.8(6) . . ?
C36 N4 H4 118.6 . . ?
C48 O6 Co1 123.5(7) . . ?
C51 O6 Co1 124.4(5) . . ?
C51 O6 C48 111.5(8) . . ?
N1 C1 H1 110.0 . . ?
N1 C1 C5 104.0(6) . . ?
C2 C1 N1 115.4(6) . . ?
C2 C1 H1 110.0 . . ?
C2 C1 C5 107.2(6) . . ?
C5 C1 H1 110.0 . . ?
C1 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
C1 C2 C3 103.5(7) . . ?
H2A C2 H2B 109.0 . . ?
C3 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
C2 C3 H3A 110.0 . . ?
C2 C3 H3B 110.0 . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 C2 108.7(7) . . ?
C4 C3 H3A 110.0 . . ?
C4 C3 H3B 110.0 . . ?
C3 C4 H4A 111.0 . . ?
C3 C4 H4B 111.0 . . ?
C3 C4 C5 103.7(8) . . ?
H4A C4 H4B 109.0 . . ?
C5 C4 H4A 111.0 . . ?
C5 C4 H4B 111.0 . . ?
C1 C5 H5 109.2 . . ?
C4 C5 C1 105.2(7) . . ?
C4 C5 H5 109.2 . . ?
C6 C5 C1 106.0(6) . . ?
C6 C5 C4 117.6(8) . . ?
C6 C5 H5 109.2 . . ?
C5 C6 H6A 111.0 . . ?
C5 C6 H6B 111.0 . . ?
H6A C6 H6B 109.0 . . ?
C7 C6 C5 103.6(7) . . ?
C7 C6 H6A 111.0 . . ?
C7 C6 H6B 111.0 . . ?
N1 C7 H7 107.3 . . ?
C6 C7 N1 102.7(5) . . ?
C6 C7 H7 107.3 . . ?
C6 C7 C8 117.7(6) . . ?
C8 C7 N1 114.0(5) . . ?
C8 C7 H7 107.3 . . ?
O2 C8 N2 120.3(6) . . ?
O2 C8 C7 124.5(5) . . ?
N2 C8 C7 115.2(6) . . ?
C10 C9 N2 119.5(7) . . ?
C14 C9 N2 118.1(8) . . ?
C14 C9 C10 122.4(7) . . ?
C9 C10 C11 117.2(9) . . ?
C9 C10 C15 122.5(7) . . ?
C11 C10 C15 120.2(9) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.8(11) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C13 121.3(10) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 118.9 . . ?
C12 C13 C14 122.2(11) . . ?
C14 C13 H13 118.9 . . ?
C9 C14 C13 115.8(10) . . ?
C9 C14 C18 120.8(8) . . ?
C13 C14 C18 123.4(9) . . ?
C10 C15 H15 108.4 . . ?
C10 C15 C17 110.1(8) . . ?
C16 C15 C10 114.7(10) . . ?
C16 C15 H15 108.4 . . ?
C16 C15 C17 106.5(13) . . ?
C17 C15 H15 108.4 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18 105.8 . . ?
C19 C18 C14 114.9(15) . . ?
C19 C18 H18 105.8 . . ?
C19 C18 C20 112.0(15) . . ?
C20 C18 C14 111.7(14) . . ?
C20 C18 H18 105.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 H21A 111.8 . . ?
O3 C21 H21B 111.8 . . ?
O3 C21 C22 99.9(13) . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21A 111.8 . . ?
C22 C21 H21B 111.8 . . ?
C21 C22 H22A 110.9 . . ?
C21 C22 H22B 110.9 . . ?
C21 C22 C23 104.5(15) . . ?
H22A C22 H22B 108.9 . . ?
C23 C22 H22A 110.9 . . ?
C23 C22 H22B 110.9 . . ?
C22 C23 H23A 111.5 . . ?
C22 C23 H23B 111.5 . . ?
H23A C23 H23B 109.3 . . ?
C24 C23 C22 101.3(16) . . ?
C24 C23 H23A 111.5 . . ?
C24 C23 H23B 111.5 . . ?
O3 C24 C23 109.4(16) . . ?
O3 C24 H24A 109.8 . . ?
O3 C24 H24B 109.8 . . ?
C23 C24 H24A 109.8 . . ?
C23 C24 H24B 109.8 . . ?
H24A C24 H24B 108.2 . . ?
N3 C25 H25 109.5 . . ?
C26 C25 N3 114.8(7) . . ?
C26 C25 H25 109.5 . . ?
C26 C25 C29 108.0(7) . . ?
C29 C25 N3 105.3(6) . . ?
C29 C25 H25 109.5 . . ?
C25 C26 H26A 110.9 . . ?
C25 C26 H26B 110.9 . . ?
C25 C26 C27 104.3(7) . . ?
H26A C26 H26B 108.9 . . ?
C27 C26 H26A 110.9 . . ?
C27 C26 H26B 110.9 . . ?
C26 C27 H27A 110.4 . . ?
C26 C27 H27B 110.4 . . ?
H27A C27 H27B 108.6 . . ?
C28 C27 C26 106.6(9) . . ?
C28 C27 H27A 110.4 . . ?
C28 C27 H27B 110.4 . . ?
C27 C28 H28A 110.4 . . ?
C27 C28 H28B 110.4 . . ?
C27 C28 C29 106.5(9) . . ?
H28A C28 H28B 108.6 . . ?
C29 C28 H28A 110.4 . . ?
C29 C28 H28B 110.4 . . ?
C25 C29 H29 109.9 . . ?
C25 C29 C30 106.0(7) . . ?
C28 C29 C25 104.9(8) . . ?
C28 C29 H29 109.9 . . ?
C28 C29 C30 115.8(11) . . ?
C30 C29 H29 109.9 . . ?
C29 C30 H30A 111.8 . . ?
C29 C30 H30B 111.8 . . ?
H30A C30 H30B 109.5 . . ?
C31 C30 C29 99.8(7) . . ?
C31 C30 H30A 111.8 . . ?
C31 C30 H30B 111.8 . . ?
N3 C31 H31 107.1 . . ?
C30 C31 N3 103.3(5) . . ?
C30 C31 H31 107.1 . . ?
C32 C31 N3 114.6(5) . . ?
C32 C31 C30 117.0(6) . . ?
C32 C31 H31 107.1 . . ?
O4 C32 N4 121.4(6) . . ?
O4 C32 C31 125.1(6) . . ?
N4 C32 C31 113.5(6) . . ?
N3 C33 H33A 108.3 . . ?
N3 C33 H33B 108.3 . . ?
N3 C33 C34 116.0(6) . . ?
H33A C33 H33B 107.4 . . ?
C34 C33 H33A 108.3 . . ?
C34 C33 H33B 108.3 . . ?
C33 C34 H34A 107.6 . . ?
C33 C34 H34B 107.6 . . ?
C33 C34 C35 118.8(6) . . ?
H34A C34 H34B 107.0 . . ?
C35 C34 H34A 107.6 . . ?
C35 C34 H34B 107.6 . . ?
N1 C35 C34 116.2(5) . . ?
N1 C35 H35A 108.2 . . ?
N1 C35 H35B 108.2 . . ?
C34 C35 H35A 108.2 . . ?
C34 C35 H35B 108.2 . . ?
H35A C35 H35B 107.4 . . ?
C37 C36 N4 120.1(7) . . ?
C41 C36 N4 117.7(7) . . ?
C41 C36 C37 122.2(7) . . ?
C36 C37 C42 121.7(7) . . ?
C38 C37 C36 117.5(8) . . ?
C38 C37 C42 120.6(8) . . ?
C37 C38 H38 120.5 . . ?
C39 C38 C37 119.1(9) . . ?
C39 C38 H38 120.5 . . ?
C38 C39 H39 117.6 . . ?
C38 C39 C40 124.8(9) . . ?
C40 C39 H39 117.6 . . ?
C39 C40 H40 121.3 . . ?
C39 C40 C41 117.4(10) . . ?
C41 C40 H40 121.3 . . ?
C36 C41 C40 118.9(9) . . ?
C36 C41 C45 122.5(8) . . ?
C40 C41 C45 118.6(9) . . ?
C37 C42 H42 107.8 . . ?
C37 C42 C43 112.5(11) . . ?
C37 C42 C44 112.4(9) . . ?
C43 C42 H42 107.8 . . ?
C44 C42 H42 107.8 . . ?
C44 C42 C43 108.2(14) . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C41 C45 H45 107.8 . . ?
C41 C45 C46 109.6(11) . . ?
C46 C45 H45 107.8 . . ?
C47 C45 C41 112.6(8) . . ?
C47 C45 H45 107.8 . . ?
C47 C45 C46 111.0(11) . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C45 C47 H47A 109.5 . . ?
C45 C47 H47B 109.5 . . ?
C45 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
O6 C48 H48A 110.7 . . ?
O6 C48 H48B 110.7 . . ?
O6 C48 C49 105.4(13) . . ?
H48A C48 H48B 108.8 . . ?
C49 C48 H48A 110.7 . . ?
C49 C48 H48B 110.7 . . ?
C48 C49 H49A 110.3 . . ?
C48 C49 H49B 110.3 . . ?
H49A C49 H49B 108.5 . . ?
C50 C49 C48 107.3(16) . . ?
C50 C49 H49A 110.3 . . ?
C50 C49 H49B 110.3 . . ?
C49 C50 H50A 110.1 . . ?
C49 C50 H50B 110.1 . . ?
C49 C50 C51 108.1(16) . . ?
H50A C50 H50B 108.4 . . ?
C51 C50 H50A 110.1 . . ?
C51 C50 H50B 110.1 . . ?
O6 C51 C50 105.2(12) . . ?
O6 C51 H51A 110.7 . . ?
O6 C51 H51B 110.7 . . ?
C50 C51 H51A 110.7 . . ?
C50 C51 H51B 110.7 . . ?
H51A C51 H51B 108.8 . . ?
O10 Cl1 O7 104.8(14) . . ?
O10 Cl1 O9 107.2(10) . . ?
O10 Cl1 O8 112.1(7) . . ?
O9 Cl1 O7 101.1(13) . . ?
O8 Cl1 O7 111.8(11) . . ?
O8 Cl1 O9 118.6(8) . . ?
O12 Cl2 O11 109.5(12) . . ?
O12 Cl2 O13 116.5(13) . . ?
O12 Cl2 O14 84.5(17) . . ?
O11 Cl2 O14 127.5(15) . . ?
O13 Cl2 O11 112.5(7) . . ?
O13 Cl2 O14 104.0(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 O1 N1 C1 -173.7(4) . . . . ?
Co1 O1 N1 C7 -65.6(5) . . . . ?
Co1 O1 N1 C35 57.9(5) . . . . ?
Co1 O2 C8 N2 -177.1(5) . . . . ?
Co1 O2 C8 C7 2.3(9) . . . . ?
Co1 O5 N3 C25 -178.1(4) . . . . ?
Co1 O5 N3 C31 -67.1(6) . . . . ?
Co1 O5 N3 C33 56.1(6) . . . . ?
Co1 O4 C32 N4 174.0(5) . . . . ?
Co1 O4 C32 C31 -4.7(9) . . . . ?
Co1 O3 C21 C22 -160.4(8) . . . . ?
Co1 O3 C24 C23 -178.7(10) . . . . ?
Co1 O6 C48 C49 172.9(10) . . . . ?
Co1 O6 C51 C50 178.3(10) . . . . ?
O1 N1 C1 C2 -40.1(8) . . . . ?
O1 N1 C1 C5 77.1(6) . . . . ?
O1 N1 C7 C6 -64.3(6) . . . . ?
O1 N1 C7 C8 64.1(6) . . . . ?
O1 N1 C35 C34 54.8(7) . . . . ?
O5 N3 C25 C26 -27.5(8) . . . . ?
O5 N3 C25 C29 91.1(7) . . . . ?
O5 N3 C31 C30 -68.5(7) . . . . ?
O5 N3 C31 C32 60.0(7) . . . . ?
O5 N3 C33 C34 56.3(7) . . . . ?
N1 C1 C2 C3 123.9(8) . . . . ?
N1 C1 C5 C4 -110.8(7) . . . . ?
N1 C1 C5 C6 14.5(7) . . . . ?
N1 C7 C8 O2 -32.7(9) . . . . ?
N1 C7 C8 N2 146.8(6) . . . . ?
N2 C9 C10 C11 179.6(8) . . . . ?
N2 C9 C10 C15 -2.3(12) . . . . ?
N2 C9 C14 C13 -179.7(8) . . . . ?
N2 C9 C14 C18 3.2(12) . . . . ?
O3 C21 C22 C23 -32.9(16) . . . . ?
N3 C25 C26 C27 100.8(9) . . . . ?
N3 C25 C29 C28 -125.3(9) . . . . ?
N3 C25 C29 C30 -2.2(10) . . . . ?
N3 C31 C32 O4 -24.2(9) . . . . ?
N3 C31 C32 N4 157.0(6) . . . . ?
N3 C33 C34 C35 -63.6(9) . . . . ?
N4 C36 C37 C38 -179.2(6) . . . . ?
N4 C36 C37 C42 -3.7(10) . . . . ?
N4 C36 C41 C40 -178.1(7) . . . . ?
N4 C36 C41 C45 2.0(11) . . . . ?
O6 C48 C49 C50 8(2) . . . . ?
C1 N1 C7 C6 49.2(6) . . . . ?
C1 N1 C7 C8 177.7(5) . . . . ?
C1 N1 C35 C34 -69.5(7) . . . . ?
C1 C2 C3 C4 -27.9(11) . . . . ?
C1 C5 C6 C7 15.8(8) . . . . ?
C2 C1 C5 C4 11.9(9) . . . . ?
C2 C1 C5 C6 137.2(7) . . . . ?
C2 C3 C4 C5 35.5(12) . . . . ?
C3 C4 C5 C1 -28.7(10) . . . . ?
C3 C4 C5 C6 -146.3(9) . . . . ?
C4 C5 C6 C7 133.0(8) . . . . ?
C5 C1 C2 C3 8.6(9) . . . . ?
C5 C6 C7 N1 -40.8(7) . . . . ?
C5 C6 C7 C8 -166.9(6) . . . . ?
C6 C7 C8 O2 87.6(8) . . . . ?
C6 C7 C8 N2 -92.9(8) . . . . ?
C7 N1 C1 C2 -155.8(6) . . . . ?
C7 N1 C1 C5 -38.6(6) . . . . ?
C7 N1 C35 C34 178.7(5) . . . . ?
C8 N2 C9 C10 -95.4(9) . . . . ?
C8 N2 C9 C14 86.0(9) . . . . ?
C9 N2 C8 O2 2.6(11) . . . . ?
C9 N2 C8 C7 -176.9(7) . . . . ?
C9 C10 C11 C12 -2.2(16) . . . . ?
C9 C10 C15 C16 133.9(12) . . . . ?
C9 C10 C15 C17 -106.0(13) . . . . ?
C9 C14 C18 C19 -136.8(14) . . . . ?
C9 C14 C18 C20 94.2(15) . . . . ?
C10 C9 C14 C13 1.6(12) . . . . ?
C10 C9 C14 C18 -175.5(9) . . . . ?
C10 C11 C12 C13 6.2(19) . . . . ?
C11 C10 C15 C16 -48.0(15) . . . . ?
C11 C10 C15 C17 72.1(14) . . . . ?
C11 C12 C13 C14 -6.4(19) . . . . ?
C12 C13 C14 C9 2.3(16) . . . . ?
C12 C13 C14 C18 179.4(11) . . . . ?
C13 C14 C18 C19 46.3(18) . . . . ?
C13 C14 C18 C20 -82.7(17) . . . . ?
C14 C9 C10 C11 -1.7(13) . . . . ?
C14 C9 C10 C15 176.4(8) . . . . ?
C15 C10 C11 C12 179.6(11) . . . . ?
C21 O3 C24 C23 -1(2) . . . . ?
C21 C22 C23 C24 33(2) . . . . ?
C22 C23 C24 O3 -20(2) . . . . ?
C24 O3 C21 C22 22.1(15) . . . . ?
C25 N3 C31 C30 46.8(7) . . . . ?
C25 N3 C31 C32 175.3(6) . . . . ?
C25 N3 C33 C34 -67.1(8) . . . . ?
C25 C26 C27 C28 29.5(11) . . . . ?
C25 C29 C30 C31 30.0(9) . . . . ?
C26 C25 C29 C28 -2.2(12) . . . . ?
C26 C25 C29 C30 120.9(8) . . . . ?
C26 C27 C28 C29 -31.5(14) . . . . ?
C27 C28 C29 C25 20.6(14) . . . . ?
C27 C28 C29 C30 -95.9(12) . . . . ?
C28 C29 C30 C31 145.8(9) . . . . ?
C29 C25 C26 C27 -16.3(10) . . . . ?
C29 C30 C31 N3 -47.5(8) . . . . ?
C29 C30 C31 C32 -174.4(7) . . . . ?
C30 C31 C32 O4 97.0(8) . . . . ?
C30 C31 C32 N4 -81.8(8) . . . . ?
C31 N3 C25 C26 -145.0(7) . . . . ?
C31 N3 C25 C29 -26.4(8) . . . . ?
C31 N3 C33 C34 -179.3(6) . . . . ?
C32 N4 C36 C37 -98.8(8) . . . . ?
C32 N4 C36 C41 80.3(9) . . . . ?
C33 N3 C25 C26 98.0(7) . . . . ?
C33 N3 C25 C29 -143.4(7) . . . . ?
C33 N3 C31 C30 166.4(6) . . . . ?
C33 N3 C31 C32 -65.1(7) . . . . ?
C33 C34 C35 N1 -62.1(8) . . . . ?
C35 N1 C1 C2 86.3(7) . . . . ?
C35 N1 C1 C5 -156.5(5) . . . . ?
C35 N1 C7 C6 171.1(5) . . . . ?
C35 N1 C7 C8 -60.5(6) . . . . ?
C36 N4 C32 O4 7.9(10) . . . . ?
C36 N4 C32 C31 -173.2(6) . . . . ?
C36 C37 C38 C39 -2.9(12) . . . . ?
C36 C37 C42 C43 130.9(12) . . . . ?
C36 C37 C42 C44 -106.6(11) . . . . ?
C36 C41 C45 C46 -120.1(10) . . . . ?
C36 C41 C45 C47 115.8(11) . . . . ?
C37 C36 C41 C40 1.0(11) . . . . ?
C37 C36 C41 C45 -178.9(8) . . . . ?
C37 C38 C39 C40 1.3(14) . . . . ?
C38 C37 C42 C43 -53.8(13) . . . . ?
C38 C37 C42 C44 68.7(12) . . . . ?
C38 C39 C40 C41 1.5(14) . . . . ?
C39 C40 C41 C36 -2.6(12) . . . . ?
C39 C40 C41 C45 177.3(9) . . . . ?
C40 C41 C45 C46 60.0(11) . . . . ?
C40 C41 C45 C47 -64.1(13) . . . . ?
C41 C36 C37 C38 1.8(11) . . . . ?
C41 C36 C37 C42 177.2(7) . . . . ?
C42 C37 C38 C39 -178.4(8) . . . . ?
C48 O6 C51 C50 -10.8(15) . . . . ?
C48 C49 C50 C51 -15(2) . . . . ?
C49 C50 C51 O6 16(2) . . . . ?
C51 O6 C48 C49 1.9(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.366
_oxdiff_exptl_absorpt_empirical_full_min 0.743
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/THF'
