# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_fdd2
_database_code_depnum_ccdc_archive 'CCDC 1419711'
_audit_update_record             
;
2015-08-19 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;
_audit_creation_date             2013-04-15
_audit_creation_method           
;
  Olex2 1.2-beta
  (compiled Apr  9 2013 14:10:59, GUI svn.r4458)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '0.13(C192 H224 Mn8 N16 O48), 2(H2 O)'
_chemical_formula_sum            'C24 H32 Mn N2 O8'
_chemical_formula_weight         531.45
_chemical_absolute_configuration ?
_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'
Mn Mn 0.3368 0.7283 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   33.046(4)
_cell_length_b                   9.0309(10)
_cell_length_c                   16.4592(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4912.0(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9879
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      37.694
_cell_measurement_theta_min      2.471
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_T_max  0.7474
_exptl_absorpt_correction_T_min  0.5594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0820 before and 0.0580 after correction.
The Ratio of minimum to maximum transmission is 0.7485.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2232
_exptl_crystal_size_max          0.888
_exptl_crystal_size_mid          0.619
_exptl_crystal_size_min          0.318
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -56
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15648
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.751
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         37.785
_diffrn_reflns_theta_min         2.465
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_device_type  'Bruker D8 diffractometer with APEX2 detector'
_diffrn_measurement_method       'φ and ω scans with a narrow frame width'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_full    0.927
_reflns_Friedel_fraction_max     0.626
_reflns_number_gt                4627
_reflns_number_total             4964
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'APEX2 v2011.2-4 (Bruker, 2011)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         1.027
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.106
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         4964
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.059
_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)+(0.0928P)²+0.2252P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1299
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 C6-H6 = C4-H4 = C3-H3
 0.999 with sigma of 0.005
 C7-H7
 0.999 with sigma of 0.005
 C10-H10A = C10-H10B
 0.999 with sigma of 0.005
 H1WA-O1W = O1W-H1WB
 0.995 with sigma of 0.02
 H1WA-O1W = O1W-H1WB
 0.995 with sigma of 0.02
 O1-H1WA
 1.81 with sigma of 0.02
 H1WA-H1WB
 1.61 with sigma of 0.04
 H1WA-H1WB
 1.61 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uiso(H6) = Uiso(H4) = Uiso(H3)
Uiso(H10B) = Uiso(H10A)
4.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C8(H8B,H8A), C12(H12A,H12B), C9(H9A,H9B)
;
_atom_sites_solution_hydrogens   mixed
_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
Mn1 Mn -0.2500 -0.7500 -1.48847(3) 0.01448(11) Uani 1 2 d S T P . .
C11 C -0.24838(9) -0.4627(4) -1.3772(3) 0.0338(7) Uani 1 1 d . . . . .
H11A H -0.2598 -0.4063 -1.3310 0.041 Uiso 1 1 calc R U . . .
H11B H -0.2411 -0.3914 -1.4205 0.041 Uiso 1 1 calc R U . . .
C5 C -0.38655(6) -0.2917(2) -1.69066(15) 0.0181(4) Uani 1 1 d . . . . .
O3 O -0.27844(6) -0.5667(2) -1.40783(14) 0.0289(4) Uani 1 1 d . . . . .
C2 C -0.32224(6) -0.4561(2) -1.62503(15) 0.0180(4) Uani 1 1 d . . . . .
C8 C -0.42116(6) -0.2040(2) -1.72655(15) 0.0202(4) Uani 1 1 d . . . . .
H8B H -0.4101 -0.1356 -1.7680 0.024 Uiso 1 1 calc R U . . .
H8A H -0.4396 -0.2735 -1.7547 0.024 Uiso 1 1 calc R U . . .
C3 C -0.31814(6) -0.3039(2) -1.63705(16) 0.0192(4) Uani 1 1 d D . . . .
C4 C -0.35015(6) -0.2233(2) -1.66977(16) 0.0196(4) Uani 1 1 d D . . . .
C1 C -0.28794(7) -0.5433(2) -1.58907(17) 0.0217(4) Uani 1 1 d . . . . .
O1 O -0.29520(5) -0.67898(19) -1.57189(13) 0.0249(4) Uani 1 1 d D . . . .
O2 O -0.25478(7) -0.4826(3) -1.57593(19) 0.0319(5) Uani 1 1 d . . . . .
C7 C -0.35836(7) -0.5259(3) -1.6466(2) 0.0248(5) Uani 1 1 d D . . . .
C6 C -0.39008(6) -0.4445(2) -1.67905(18) 0.0244(5) Uani 1 1 d D . . . .
N1 N -0.30456(6) -0.8653(3) -1.41681(14) 0.0255(4) Uani 1 1 d . . . . .
C12 C -0.21121(9) -0.5450(4) -1.3500(2) 0.0338(6) Uani 1 1 d . . . . .
H12A H -0.1903 -0.4737 -1.3321 0.041 Uiso 1 1 calc R U . . .
H12B H -0.2180 -0.6097 -1.3035 0.041 Uiso 1 1 calc R U . . .
C10 C -0.30498(9) -0.6181(4) -1.3466(2) 0.0364(7) Uani 1 1 d D . . . .
C9 C -0.33027(9) -0.7411(3) -1.3853(2) 0.0341(7) Uani 1 1 d . . . . .
H9A H -0.3495 -0.7805 -1.3445 0.041 Uiso 1 1 calc R U . . .
H9B H -0.3463 -0.6992 -1.4307 0.041 Uiso 1 1 calc R U . . .
O1W O -0.30193(10) -0.8987(3) -1.69293(18) 0.0463(6) Uani 1 1 d D . . . .
H1WA H -0.3059(16) -0.812(5) -1.656(3) 0.069 Uiso 1 1 d D U . . .
H1WB H -0.2789(13) -0.959(6) -1.673(3) 0.069 Uiso 1 1 d D U . . .
H4 H -0.3455(12) -0.1178(15) -1.685(2) 0.023(5) Uiso 1 1 d D . . . .
H3 H -0.2913(5) -0.257(3) -1.626(3) 0.023(5) Uiso 1 1 d D . . . .
H6 H -0.4143(7) -0.505(3) -1.693(3) 0.023(5) Uiso 1 1 d D . . . .
H7 H -0.3615(13) -0.6354(10) -1.641(3) 0.032(10) Uiso 1 1 d D . . . .
H10A H -0.3241(11) -0.535(4) -1.336(3) 0.043(8) Uiso 1 1 d D . . . .
H10B H -0.2883(13) -0.663(5) -1.302(2) 0.043(8) Uiso 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
Mn1 O3 2.3203(19) . ?
Mn1 O3 2.3203(19) 14_435 ?
Mn1 O1 2.1278(18) . ?
Mn1 O1 2.1278(18) 14_435 ?
Mn1 N1 2.393(2) 14_435 ?
Mn1 N1 2.393(2) . ?
C11 O3 1.457(3) . ?
C11 C12 1.504(5) . ?
C5 C8 1.511(3) . ?
C5 C4 1.395(3) . ?
C5 C6 1.398(3) . ?
O3 C10 1.414(4) . ?
C2 C3 1.395(3) . ?
C2 C1 1.502(3) . ?
C2 C7 1.396(3) . ?
C8 N1 1.501(3) 7_454 ?
C3 C4 1.392(3) . ?
C1 O1 1.280(3) . ?
C1 O2 1.244(3) . ?
C7 C6 1.388(3) . ?
N1 C8 1.501(3) 3_445 ?
N1 C12 1.461(4) 14_435 ?
N1 C9 1.499(4) . ?
C12 N1 1.461(4) 14_435 ?
C10 C9 1.529(4) . ?

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
O3 Mn1 O3 110.22(12) . 14_435 ?
O3 Mn1 N1 73.93(7) . . ?
O3 Mn1 N1 73.32(8) 14_435 . ?
O3 Mn1 N1 73.31(8) . 14_435 ?
O3 Mn1 N1 73.93(7) 14_435 14_435 ?
O1 Mn1 O3 150.28(7) 14_435 . ?
O1 Mn1 O3 150.28(7) . 14_435 ?
O1 Mn1 O3 82.52(8) . . ?
O1 Mn1 O3 82.52(8) 14_435 14_435 ?
O1 Mn1 O1 99.63(11) 14_435 . ?
O1 Mn1 N1 135.71(8) 14_435 . ?
O1 Mn1 N1 85.43(8) . . ?
O1 Mn1 N1 135.71(8) . 14_435 ?
O1 Mn1 N1 85.43(8) 14_435 14_435 ?
N1 Mn1 N1 120.94(11) 14_435 . ?
O3 C11 C12 109.9(3) . . ?
C4 C5 C8 121.11(19) . . ?
C4 C5 C6 118.37(18) . . ?
C6 C5 C8 120.52(19) . . ?
C11 O3 Mn1 112.43(17) . . ?
C10 O3 Mn1 115.13(17) . . ?
C10 O3 C11 112.9(2) . . ?
C3 C2 C1 119.95(19) . . ?
C3 C2 C7 119.47(19) . . ?
C7 C2 C1 120.58(19) . . ?
N1 C8 C5 115.4(2) 7_454 . ?
C4 C3 C2 119.76(18) . . ?
C3 C4 C5 121.24(19) . . ?
O1 C1 C2 116.6(2) . . ?
O2 C1 C2 120.2(2) . . ?
O2 C1 O1 123.2(2) . . ?
C1 O1 Mn1 107.43(15) . . ?
C6 C7 C2 120.3(2) . . ?
C7 C6 C5 120.8(2) . . ?
C8 N1 Mn1 108.19(14) 3_445 . ?
C12 N1 Mn1 110.07(16) 14_435 . ?
C12 N1 C8 112.8(2) 14_435 3_445 ?
C12 N1 C9 110.9(3) 14_435 . ?
C9 N1 Mn1 105.78(16) . . ?
C9 N1 C8 108.8(2) . 3_445 ?
N1 C12 C11 110.0(3) 14_435 . ?
O3 C10 C9 106.3(3) . . ?
N1 C9 C10 112.2(2) . . ?

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
O1W H1WA O1 0.999(16) 1.87(2) 2.821(3) 158(4) .
O1W H1WB O2 0.990(18) 2.02(4) 2.893(4) 146(5) 14_435

_shelx_estimated_absorpt_T_max   0.835
_shelx_estimated_absorpt_T_min   0.623
_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.
;
_shelxl_version_number           2012-9
####################################################################### 
# 
# 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_92_58-67-co
_database_code_depnum_ccdc_archive 'CCDC 1419712'
_audit_update_record             
;
2015-08-19 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;
_audit_creation_date             2015-06-22
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2015.06.08 svn.r3188 for OlexSys, GUI svn.r5058)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H32 Co N2 O8'
_chemical_formula_sum            'C24 H32 Co N2 O8'
_chemical_formula_weight         535.44
_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 0.0033 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'
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           8
_space_group_name_H-M_alt        'C 1 m 1'
_space_group_name_Hall           'C -2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'

_cell_length_a                   9.7472(9)
_cell_length_b                   22.777(2)
_cell_length_c                   7.0903(7)
_cell_angle_alpha                90
_cell_angle_beta                 131.453(6)
_cell_angle_gamma                90
_cell_volume                     1179.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3256
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.178
_cell_measurement_theta_min      2.928
_shelx_estimated_absorpt_T_max   0.953
_shelx_estimated_absorpt_T_min   0.732
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0745 before and 0.0511 after correction.
The Ratio of minimum to maximum transmission is 0.8469.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             562
_exptl_crystal_size_max          0.427
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.062
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0599
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4351
_diffrn_reflns_point_group_measured_fraction_full 0.702
_diffrn_reflns_point_group_measured_fraction_max 0.669
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.569
_diffrn_reflns_theta_min         1.788
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_current           35
_diffrn_source_voltage           45
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.344
_reflns_Friedel_fraction_full    0.402
_reflns_Friedel_fraction_max     0.344
_reflns_number_gt                2072
_reflns_number_total             2263
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.11 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.853
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 
;
 Flack x determined using 474 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.033(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2263
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.030
_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)+(0.0455P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0918
_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 H(H) groups
2. Restrained distances
 O6-H6
 0.995 with sigma of 0.005
 O5-H5
 0.995 with sigma of 0.005
 H5_$1-H5
 1.565 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C3(H3A,H3B), C2(H2A,H2B), C1(H1A,H1B), C4(H4A,H4B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C11(H11), C8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 -0.48006(7) 0.0000 -0.70133(8) 0.01361(17) Uani 1 2 d S T P . .
O1 O -0.7211(6) 0.0000 -1.0858(7) 0.0156(9) Uani 1 2 d S T P . .
O6 O -0.2603(6) 0.0000 -0.3258(7) 0.0185(9) Uani 1 2 d DS T P . .
O2 O -0.6525(6) 0.0000 -0.6183(8) 0.0173(9) Uani 1 2 d S T P . .
O5 O -0.3360(6) 0.0000 -0.8134(8) 0.0179(9) Uani 1 2 d DS T P . .
O3 O -0.6139(4) -0.40485(12) -1.0445(5) 0.0219(6) Uani 1 1 d . . . . .
C6 C -0.4500(5) -0.20034(15) -0.6825(8) 0.0166(8) Uani 1 1 d . . . . .
N1 N -0.5620(4) -0.09455(13) -0.7513(5) 0.0152(6) Uani 1 1 d . . . . .
C12 C -0.6195(5) -0.38173(16) -0.8884(7) 0.0179(7) Uani 1 1 d . . . . .
C9 C -0.5527(5) -0.31888(16) -0.8106(7) 0.0158(7) Uani 1 1 d . . . . .
C5 C -0.4008(5) -0.13564(16) -0.6216(7) 0.0170(7) Uani 1 1 d . . . . .
H5A H -0.3229 -0.1304 -0.4412 0.020 Uiso 1 1 calc R . . . .
H5B H -0.3302 -0.1245 -0.6676 0.020 Uiso 1 1 calc R . . . .
C7 C -0.4685(6) -0.23593(19) -0.5405(7) 0.0185(9) Uani 1 1 d . . . . .
H7 H -0.4448 -0.2205 -0.4000 0.022 Uiso 1 1 calc R . . . .
C3 C -0.6617(5) -0.10267(17) -0.6589(7) 0.0189(8) Uani 1 1 d . . . . .
H3A H -0.6256 -0.1398 -0.5701 0.023 Uiso 1 1 calc R . . . .
H3B H -0.7923 -0.1042 -0.8018 0.023 Uiso 1 1 calc R . . . .
C10 C -0.5261(5) -0.28437(17) -0.9462(7) 0.0183(8) Uani 1 1 d . . . . .
H10 H -0.5415 -0.3007 -1.0794 0.022 Uiso 1 1 calc R . . . .
C11 C -0.4768(6) -0.22594(19) -0.8842(8) 0.0186(9) Uani 1 1 d . . . . .
H11 H -0.4613 -0.2033 -0.9781 0.022 Uiso 1 1 calc R . . . .
C2 C -0.6910(5) -0.10272(17) -1.0299(7) 0.0171(8) Uani 1 1 d . . . . .
H2A H -0.7557 -0.1396 -1.0736 0.021 Uiso 1 1 calc R . . . .
H2B H -0.6218 -0.1047 -1.0836 0.021 Uiso 1 1 calc R . . . .
O4 O -0.6742(5) -0.40571(13) -0.7910(7) 0.0399(9) Uani 1 1 d . . . . .
C1 C -0.8279(5) -0.05319(16) -1.1670(7) 0.0185(8) Uani 1 1 d . . . . .
H1A H -0.9062 -0.0581 -1.3476 0.022 Uiso 1 1 calc R . . . .
H1B H -0.9039 -0.0521 -1.1240 0.022 Uiso 1 1 calc R . . . .
C8 C -0.5221(5) -0.29434(17) -0.6066(7) 0.0185(8) Uani 1 1 d . . . . .
H8 H -0.5376 -0.3171 -0.5130 0.022 Uiso 1 1 calc R . . . .
C4 C -0.6216(6) -0.05361(16) -0.4858(7) 0.0198(8) Uani 1 1 d . . . . .
H4A H -0.7025 -0.0558 -0.4512 0.024 Uiso 1 1 calc R . . . .
H4B H -0.4960 -0.0557 -0.3278 0.024 Uiso 1 1 calc R . . . .
H6 H -0.204(7) -0.0356(14) -0.218(8) 0.049(16) Uiso 1 1 d D . . . .
H5 H -0.267(5) -0.0343(3) -0.799(12) 0.073 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
Co1 O1 2.115(4) . ?
Co1 O6 2.031(4) . ?
Co1 O2 2.117(4) . ?
Co1 O5 2.020(4) . ?
Co1 N1 2.242(3) . ?
Co1 N1 2.242(3) 2 ?
O1 C1 1.446(4) . ?
O1 C1 1.446(4) 2 ?
O6 H6 0.994(6) . ?
O2 C4 1.445(4) . ?
O2 C4 1.445(4) 2 ?
O5 H5 0.993(6) . ?
O3 C12 1.259(5) . ?
C6 C5 1.521(5) . ?
C6 C7 1.395(6) . ?
C6 C11 1.399(6) . ?
N1 C5 1.509(5) . ?
N1 C3 1.500(5) . ?
N1 C2 1.493(4) . ?
C12 C9 1.517(5) . ?
C12 O4 1.245(5) . ?
C9 C10 1.393(5) . ?
C9 C8 1.386(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C7 H7 0.9300 . ?
C7 C8 1.392(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.507(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(6) . ?
C11 H11 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.510(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C8 H8 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 O2 87.11(16) . . ?
O1 Co1 N1 79.68(8) . . ?
O1 Co1 N1 79.68(8) . 2 ?
O6 Co1 O1 175.8(2) . . ?
O6 Co1 O2 88.72(18) . . ?
O6 Co1 N1 99.40(8) . 2 ?
O6 Co1 N1 99.40(8) . . ?
O2 Co1 N1 77.20(8) . 2 ?
O2 Co1 N1 77.20(8) . . ?
O5 Co1 O1 87.78(17) . . ?
O5 Co1 O6 96.39(18) . . ?
O5 Co1 O2 174.89(19) . . ?
O5 Co1 N1 101.87(8) . 2 ?
O5 Co1 N1 101.87(8) . . ?
N1 Co1 N1 147.70(16) . 2 ?
C1 O1 Co1 113.9(2) . . ?
C1 O1 Co1 113.9(2) 2 . ?
C1 O1 C1 113.9(4) . 2 ?
Co1 O6 H6 125(3) . . ?
C4 O2 Co1 108.6(2) . . ?
C4 O2 Co1 108.6(2) 2 . ?
C4 O2 C4 115.3(4) . 2 ?
Co1 O5 H5 124(2) . . ?
C7 C6 C5 121.7(4) . . ?
C7 C6 C11 118.0(3) . . ?
C11 C6 C5 120.3(4) . . ?
C5 N1 Co1 112.4(2) . . ?
C3 N1 Co1 108.4(2) . . ?
C3 N1 C5 111.8(3) . . ?
C2 N1 Co1 103.2(2) . . ?
C2 N1 C5 110.7(3) . . ?
C2 N1 C3 109.9(3) . . ?
O3 C12 C9 117.2(3) . . ?
O4 C12 O3 126.1(4) . . ?
O4 C12 C9 116.8(4) . . ?
C10 C9 C12 120.8(3) . . ?
C8 C9 C12 120.3(3) . . ?
C8 C9 C10 118.9(3) . . ?
C6 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
N1 C5 C6 115.0(3) . . ?
N1 C5 H5A 108.5 . . ?
N1 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.7(4) . . ?
C8 C7 H7 119.6 . . ?
N1 C3 H3A 109.3 . . ?
N1 C3 H3B 109.3 . . ?
N1 C3 C4 111.7(3) . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10 119.8 . . ?
C6 C11 H11 119.5 . . ?
C10 C11 C6 121.1(4) . . ?
C10 C11 H11 119.5 . . ?
N1 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
N1 C2 C1 111.7(3) . . ?
H2A C2 H2B 107.9 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
O1 C1 C2 105.8(3) . . ?
O1 C1 H1A 110.6 . . ?
O1 C1 H1B 110.6 . . ?
C2 C1 H1A 110.6 . . ?
C2 C1 H1B 110.6 . . ?
H1A C1 H1B 108.7 . . ?
C9 C8 C7 120.7(4) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
O2 C4 C3 105.5(3) . . ?
O2 C4 H4A 110.6 . . ?
O2 C4 H4B 110.6 . . ?
C3 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
H4A C4 H4B 108.8 . . ?

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 C1 C2 -37.8(4) . . . . ?
Co1 O2 C4 C3 -57.9(3) . . . . ?
Co1 N1 C5 C6 -170.6(3) . . . . ?
Co1 N1 C3 C4 -19.5(4) . . . . ?
Co1 N1 C2 C1 -45.9(3) . . . . ?
O3 C12 C9 C10 14.0(5) . . . . ?
O3 C12 C9 C8 -167.8(3) . . . . ?
C6 C7 C8 C9 2.0(6) . . . . ?
N1 C3 C4 O2 50.4(4) . . . . ?
N1 C2 C1 O1 57.1(4) . . . . ?
C12 C9 C10 C11 175.7(4) . . . . ?
C12 C9 C8 C7 -177.2(4) . . . . ?
C9 C10 C11 C6 0.9(6) . . . . ?
C5 C6 C7 C8 176.9(3) . . . . ?
C5 C6 C11 C10 -178.4(4) . . . . ?
C5 N1 C3 C4 104.9(3) . . . . ?
C5 N1 C2 C1 -166.4(3) . . . . ?
C7 C6 C5 N1 -89.9(4) . . . . ?
C7 C6 C11 C10 2.1(6) . . . . ?
C3 N1 C5 C6 67.2(4) . . . . ?
C3 N1 C2 C1 69.6(4) . . . . ?
C10 C9 C8 C7 1.0(6) . . . . ?
C11 C6 C5 N1 90.6(4) . . . . ?
C11 C6 C7 C8 -3.5(6) . . . . ?
C2 N1 C5 C6 -55.8(4) . . . . ?
C2 N1 C3 C4 -131.7(3) . . . . ?
O4 C12 C9 C10 -166.2(4) . . . . ?
O4 C12 C9 C8 12.0(6) . . . . ?
C1 O1 C1 C2 -170.8(2) 2 . . . ?
C8 C9 C10 C11 -2.5(6) . . . . ?
C4 O2 C4 C3 -179.9(3) 2 . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id 92_58-67-Co
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ligand1
_database_code_depnum_ccdc_archive 'CCDC 1452096'
_audit_update_record             
;
2016-02-08 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;
_audit_creation_date             2015-11-12
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2015.10.28 svn.r3245 for OlexSys, GUI svn.r5128)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H32 N2 O6, 2(Cl), H2 O'
_chemical_formula_sum            'C24 H34 Cl2 N2 O7'
_chemical_formula_weight         533.43
_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 0.0030 0.0020 '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 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   10.6102(10)
_cell_length_b                   21.855(2)
_cell_length_c                   22.183(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5143.9(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.108
_cell_measurement_theta_min      2.323
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1710 before and 0.0699 after correction.
The Ratio of minimum to maximum transmission is 0.8380.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          0.272
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.128
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0877
_diffrn_reflns_av_unetI/netI     0.0940
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            36384
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.864
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           35
_diffrn_source_voltage           45
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.947
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                8549
_reflns_number_total             11495
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.11 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2015)'
_refine_diff_density_max         1.202
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.28(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     650
_refine_ls_number_reflns         11495
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0641
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0647P)²+3.3567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1515
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.72(9) 0.28(9)
2. 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 O(H) groups, All O(H,H) groups
3. Restrained distances
 H1WA-O1W = O1W-H1WB
 0.995 with sigma of 0.02
 O2W-H2WA
 0.995 with sigma of 0.005
 H2WA-O2W = O2W-H2WB
 0.995 with sigma of 0.02
 H1WA-H1WB
 1.62 with sigma of 0.04
 H2WA-H2WB
 1.62 with sigma of 0.04
4.a Ternary CH refined with riding coordinates:
 N1(H1), N2(H2A), N4(H4A), N3(H3A)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C13(H13A,H13B), C8(H8A,H8B), C12(H12A,H12B), C14(H14A,H14B),
 C11(H11A,H11B), C6(H6A,H6B), C10(H10A,H10B), C15(H15A,H15B), C9(H9A,H9B),
 C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B), C39(H39A,H39B), C33(H33A,H33B),
  C37(H37A,H37B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C38(H38A,H38B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C23(H23), C24(H24), C17(H17), C18(H18), C4(H4), C21(H21), C22(H22),
 C47(H47), C42(H42), C27(H27), C41(H41), C48(H48), C28(H28), C46(H46), C45(H45)
4.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O5(H5), O7(H7), O11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O1 O -1.0783(4) 0.0829(2) 1.1225(2) 0.0206(10) Uani 1 1 d . . . . .
O3 O -0.4327(4) 0.18487(19) 0.8354(2) 0.0162(10) Uani 1 1 d . . . . .
O4 O -0.2702(4) 0.09505(19) 0.9083(2) 0.0156(9) Uani 1 1 d . . . . .
O2 O -0.9172(4) 0.0420(2) 1.1743(2) 0.0213(10) Uani 1 1 d . . . . .
H2 H -0.9704 0.0408 1.2023 0.032 Uiso 1 1 calc GR . . . .
O5 O 0.3458(4) 0.1928(2) 0.6374(2) 0.0255(11) Uani 1 1 d . . . . .
H5 H 0.4050 0.2123 0.6210 0.038 Uiso 1 1 calc GR . . . .
O6 O 0.2372(5) 0.2215(2) 0.5543(2) 0.0297(11) Uani 1 1 d . . . . .
N1 N -0.5390(5) 0.0949(2) 0.9155(2) 0.0127(11) Uani 1 1 d . . . . .
H1 H -0.4879 0.0861 0.8786 0.015 Uiso 1 1 calc R . . . .
N2 N -0.2263(5) 0.1247(2) 0.7797(2) 0.0133(11) Uani 1 1 d . . . . .
H2A H -0.3042 0.1046 0.7955 0.016 Uiso 1 1 calc R . . . .
C3 C -0.9185(6) 0.0928(3) 1.0190(3) 0.0139(13) Uani 1 1 d . . . . .
H3 H -0.9920 0.1176 1.0186 0.017 Uiso 1 1 calc R . . . .
C7 C -0.5819(6) 0.1605(3) 0.9098(3) 0.0157(13) Uani 1 1 d . . . . .
H7A H -0.5320 0.1867 0.9372 0.019 Uiso 1 1 calc R . . . .
H7B H -0.6718 0.1638 0.9214 0.019 Uiso 1 1 calc R . . . .
C23 C -0.7051(6) 0.0192(3) 1.0204(3) 0.0165(14) Uani 1 1 d . . . . .
H23 H -0.6326 -0.0063 1.0206 0.020 Uiso 1 1 calc R . . . .
C1 C -0.9719(5) 0.0625(3) 1.1245(3) 0.0152(13) Uani 1 1 d . . . . .
C13 C -0.3291(6) 0.1168(3) 0.9617(3) 0.0155(13) Uani 1 1 d . . . . .
H13A H -0.3432 0.1615 0.9589 0.019 Uiso 1 1 calc R . . . .
H13B H -0.2750 0.1086 0.9971 0.019 Uiso 1 1 calc R . . . .
C8 C -0.5650(5) 0.1818(3) 0.8454(3) 0.0155(13) Uani 1 1 d . . . . .
H8A H -0.6045 0.1525 0.8171 0.019 Uiso 1 1 calc R . . . .
H8B H -0.6040 0.2225 0.8396 0.019 Uiso 1 1 calc R . . . .
C24 C -0.7804(6) 0.0221(3) 1.0710(3) 0.0156(14) Uani 1 1 d . . . . .
H24 H -0.7590 -0.0008 1.1059 0.019 Uiso 1 1 calc R . . . .
C2 C -0.8879(6) 0.0587(3) 1.0707(3) 0.0161(13) Uani 1 1 d . . . . .
C5 C -0.7340(6) 0.0534(3) 0.9687(3) 0.0137(13) Uani 1 1 d . . . . .
C12 C -0.1721(6) 0.1354(3) 0.8886(3) 0.0176(14) Uani 1 1 d . . . . .
H12A H -0.1009 0.1340 0.9175 0.021 Uiso 1 1 calc R . . . .
H12B H -0.2041 0.1780 0.8871 0.021 Uiso 1 1 calc R . . . .
C17 C 0.0411(6) 0.1041(3) 0.7101(3) 0.0183(14) Uani 1 1 d . . . . .
H17 H 0.0519 0.0776 0.7437 0.022 Uiso 1 1 calc R . . . .
C14 C -0.4538(6) 0.0837(3) 0.9681(3) 0.0168(14) Uani 1 1 d . . . . .
H14A H -0.4378 0.0392 0.9718 0.020 Uiso 1 1 calc R . . . .
H14B H -0.4961 0.0975 1.0054 0.020 Uiso 1 1 calc R . . . .
C11 C -0.1280(6) 0.1163(3) 0.8273(3) 0.0169(14) Uani 1 1 d . . . . .
H11A H -0.0524 0.1404 0.8164 0.020 Uiso 1 1 calc R . . . .
H11B H -0.1032 0.0726 0.8286 0.020 Uiso 1 1 calc R . . . .
C20 C 0.2438(7) 0.1962(3) 0.6029(3) 0.0216(15) Uani 1 1 d . . . . .
C6 C -0.6494(6) 0.0499(3) 0.9142(3) 0.0172(14) Uani 1 1 d . . . . .
H6A H -0.7005 0.0579 0.8777 0.021 Uiso 1 1 calc R . . . .
H6B H -0.6156 0.0078 0.9110 0.021 Uiso 1 1 calc R . . . .
C18 C 0.1464(6) 0.1296(3) 0.6820(3) 0.0211(15) Uani 1 1 d . . . . .
H18 H 0.2284 0.1216 0.6973 0.025 Uiso 1 1 calc R . . . .
C10 C -0.2613(6) 0.1907(3) 0.7685(3) 0.0190(14) Uani 1 1 d . . . . .
H10A H -0.2346 0.2027 0.7274 0.023 Uiso 1 1 calc R . . . .
H10B H -0.2165 0.2172 0.7976 0.023 Uiso 1 1 calc R . . . .
C16 C -0.0797(6) 0.1173(3) 0.6894(3) 0.0158(13) Uani 1 1 d . . . . .
C4 C -0.8416(6) 0.0901(3) 0.9688(3) 0.0183(14) Uani 1 1 d . . . . .
H4 H -0.8621 0.1135 0.9340 0.022 Uiso 1 1 calc R . . . .
C19 C 0.1319(6) 0.1666(2) 0.6318(3) 0.0186(14) Uani 1 1 d . . . . .
C15 C -0.1937(6) 0.0913(3) 0.7215(3) 0.0184(14) Uani 1 1 d . . . . .
H15A H -0.1777 0.0477 0.7309 0.022 Uiso 1 1 calc R . . . .
H15B H -0.2671 0.0932 0.6940 0.022 Uiso 1 1 calc R . . . .
C9 C -0.4017(6) 0.1998(3) 0.7749(3) 0.0191(14) Uani 1 1 d . . . . .
H9A H -0.4245 0.2428 0.7661 0.023 Uiso 1 1 calc R . . . .
H9B H -0.4477 0.1729 0.7466 0.023 Uiso 1 1 calc R . . . .
C21 C 0.0126(7) 0.1777(3) 0.6099(3) 0.0212(15) Uani 1 1 d . . . . .
H21 H 0.0022 0.2024 0.5750 0.025 Uiso 1 1 calc R . . . .
C22 C -0.0930(6) 0.1533(3) 0.6382(3) 0.0207(15) Uani 1 1 d . . . . .
H22 H -0.1746 0.1612 0.6224 0.025 Uiso 1 1 calc R . . . .
O10 O 0.0470(4) 0.32149(19) 0.6712(2) 0.0172(10) Uani 1 1 d . . . . .
O9 O 0.2212(4) 0.40247(18) 0.5957(2) 0.0166(10) Uani 1 1 d . . . . .
O7 O -0.3966(4) 0.4542(2) 0.3208(2) 0.0236(11) Uani 1 1 d . . . . .
H7 H -0.4464 0.4541 0.2913 0.035 Uiso 1 1 calc GR . . . .
O8 O -0.5666(4) 0.4204(2) 0.3708(2) 0.0234(11) Uani 1 1 d . . . . .
O11 O 0.7641(4) 0.2948(2) 0.9165(2) 0.0300(12) Uani 1 1 d . . . . .
H11 H 0.8106 0.2818 0.9443 0.045 Uiso 1 1 calc GR . . . .
O12 O 0.6072(5) 0.2692(2) 0.9794(2) 0.0262(11) Uani 1 1 d . . . . .
N4 N 0.2663(5) 0.3773(2) 0.7185(2) 0.0135(11) Uani 1 1 d . . . . .
H4A H 0.1919 0.3973 0.6991 0.016 Uiso 1 1 calc R . . . .
N3 N -0.0567(5) 0.4095(2) 0.5914(2) 0.0128(11) Uani 1 1 d . . . . .
H3A H -0.0062 0.4193 0.6282 0.015 Uiso 1 1 calc R . . . .
C34 C 0.3712(6) 0.3801(3) 0.6728(3) 0.0169(14) Uani 1 1 d . . . . .
H34A H 0.4398 0.3519 0.6848 0.020 Uiso 1 1 calc R . . . .
H34B H 0.4060 0.4221 0.6713 0.020 Uiso 1 1 calc R . . . .
C40 C 0.3907(6) 0.3863(3) 0.8155(3) 0.0155(13) Uani 1 1 d . . . . .
C26 C -0.3822(6) 0.4430(3) 0.4264(3) 0.0140(13) Uani 1 1 d . . . . .
C47 C -0.3482(6) 0.4150(3) 0.5300(3) 0.0154(13) Uani 1 1 d . . . . .
H47 H -0.3732 0.3924 0.5645 0.019 Uiso 1 1 calc R . . . .
C25 C -0.4589(6) 0.4375(3) 0.3709(3) 0.0177(14) Uani 1 1 d . . . . .
C35 C 0.2256(6) 0.3127(3) 0.7331(3) 0.0171(14) Uani 1 1 d . . . . .
H35A H 0.2635 0.2840 0.7036 0.021 Uiso 1 1 calc R . . . .
H35B H 0.2563 0.3014 0.7737 0.021 Uiso 1 1 calc R . . . .
C42 C 0.6045(6) 0.3608(3) 0.8428(3) 0.0203(14) Uani 1 1 d . . . . .
H42 H 0.6925 0.3633 0.8352 0.024 Uiso 1 1 calc R . . . .
C27 C -0.2755(6) 0.4804(3) 0.4283(3) 0.0159(14) Uani 1 1 d . . . . .
H27 H -0.2501 0.5025 0.3935 0.019 Uiso 1 1 calc R . . . .
C41 C 0.5195(6) 0.3898(3) 0.8043(3) 0.0164(13) Uani 1 1 d . . . . .
H41 H 0.5495 0.4120 0.7704 0.020 Uiso 1 1 calc R . . . .
C36 C 0.0847(6) 0.3070(3) 0.7311(3) 0.0189(14) Uani 1 1 d . . . . .
H36A H 0.0587 0.2648 0.7416 0.023 Uiso 1 1 calc R . . . .
H36B H 0.0454 0.3356 0.7602 0.023 Uiso 1 1 calc R . . . .
C39 C 0.2960(6) 0.4153(3) 0.7742(3) 0.0155(13) Uani 1 1 d . . . . .
H39A H 0.3283 0.4557 0.7612 0.019 Uiso 1 1 calc R . . . .
H39B H 0.2170 0.4223 0.7969 0.019 Uiso 1 1 calc R . . . .
C48 C -0.4187(6) 0.4113(3) 0.4771(3) 0.0155(14) Uani 1 1 d . . . . .
H48 H -0.4925 0.3867 0.4760 0.019 Uiso 1 1 calc R . . . .
C29 C -0.2415(6) 0.4517(3) 0.5324(3) 0.0156(14) Uani 1 1 d . . . . .
C33 C 0.3226(6) 0.3623(3) 0.6109(3) 0.0171(14) Uani 1 1 d . . . . .
H33A H 0.3909 0.3659 0.5808 0.020 Uiso 1 1 calc R . . . .
H33B H 0.2927 0.3194 0.6114 0.020 Uiso 1 1 calc R . . . .
C28 C -0.2066(6) 0.4852(3) 0.4815(3) 0.0171(14) Uani 1 1 d . . . . .
H28 H -0.1353 0.5115 0.4832 0.021 Uiso 1 1 calc R . . . .
C46 C 0.3486(6) 0.3553(3) 0.8666(3) 0.0170(14) Uani 1 1 d . . . . .
H46 H 0.2610 0.3540 0.8753 0.020 Uiso 1 1 calc R . . . .
C43 C 0.5607(6) 0.3286(3) 0.8921(3) 0.0195(15) Uani 1 1 d . . . . .
C37 C -0.0862(6) 0.3247(3) 0.6637(3) 0.0174(14) Uani 1 1 d . . . . .
H37A H -0.1233 0.3545 0.6923 0.021 Uiso 1 1 calc R . . . .
H37B H -0.1252 0.2842 0.6708 0.021 Uiso 1 1 calc R . . . .
C45 C 0.4326(6) 0.3266(3) 0.9045(3) 0.0195(14) Uani 1 1 d . . . . .
H45 H 0.4029 0.3055 0.9391 0.023 Uiso 1 1 calc R . . . .
C30 C -0.1628(6) 0.4562(3) 0.5890(3) 0.0161(13) Uani 1 1 d . . . . .
H30A H -0.2181 0.4504 0.6245 0.019 Uiso 1 1 calc R . . . .
H30B H -0.1262 0.4978 0.5916 0.019 Uiso 1 1 calc R . . . .
C44 C 0.6460(6) 0.2953(3) 0.9349(3) 0.0203(14) Uani 1 1 d . . . . .
C31 C 0.0313(6) 0.4161(3) 0.5387(3) 0.0161(14) Uani 1 1 d . . . . .
H31A H 0.0534 0.4599 0.5339 0.019 Uiso 1 1 calc R . . . .
H31B H -0.0127 0.4028 0.5016 0.019 Uiso 1 1 calc R . . . .
C32 C 0.1510(6) 0.3794(3) 0.5456(3) 0.0176(14) Uani 1 1 d . . . . .
H32A H 0.1302 0.3358 0.5523 0.021 Uiso 1 1 calc R . . . .
H32B H 0.2021 0.3826 0.5084 0.021 Uiso 1 1 calc R . . . .
C38 C -0.1069(6) 0.3449(3) 0.6001(3) 0.0195(15) Uani 1 1 d . . . . .
H38A H -0.1981 0.3438 0.5907 0.023 Uiso 1 1 calc R . . . .
H38B H -0.0631 0.3166 0.5723 0.023 Uiso 1 1 calc R . . . .
Cl4 Cl -0.40882(13) 0.26620(7) 0.62842(8) 0.0180(3) Uani 1 1 d . . . . .
Cl2 Cl 0.04476(14) 0.47490(6) 0.70427(7) 0.0166(3) Uani 1 1 d . . . . .
Cl1 Cl -0.45107(14) 0.03372(6) 0.79581(7) 0.0159(3) Uani 1 1 d . . . . .
Cl3 Cl 0.12738(14) 0.21192(7) 0.85234(8) 0.0205(3) Uani 1 1 d . . . . .
O1W O 0.1338(5) 0.2883(2) 0.9672(3) 0.0322(12) Uani 1 1 d D . . . .
H1WA H 0.170(7) 0.260(3) 0.998(2) 0.048 Uiso 1 1 d DR . . . .
H1WB H 0.134(8) 0.263(3) 0.929(2) 0.048 Uiso 1 1 d DR . . . .
O2W O -0.4041(5) 0.2385(2) 0.4916(3) 0.0315(12) Uani 1 1 d D . . . .
H2WA H -0.484(4) 0.258(3) 0.477(3) 0.05(3) Uiso 1 1 d D . . . .
H2WB H -0.396(8) 0.245(5) 0.5361(15) 0.09(4) Uiso 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
O1 C1 1.216(7) . ?
O3 C8 1.423(7) . ?
O3 C9 1.419(8) . ?
O4 C13 1.422(7) . ?
O4 C12 1.433(7) . ?
O2 H2 0.8400 . ?
O2 C1 1.324(8) . ?
O5 H5 0.8400 . ?
O5 C20 1.327(9) . ?
O6 C20 1.214(9) . ?
N1 H1 1.0000 . ?
N1 C7 1.510(7) . ?
N1 C14 1.496(8) . ?
N1 C6 1.529(8) . ?
N2 H2A 1.0000 . ?
N2 C11 1.496(8) . ?
N2 C10 1.509(7) . ?
N2 C15 1.523(8) . ?
C3 H3 0.9500 . ?
C3 C2 1.406(9) . ?
C3 C4 1.382(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.512(9) . ?
C23 H23 0.9500 . ?
C23 C24 1.378(9) . ?
C23 C5 1.401(9) . ?
C1 C2 1.492(9) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.515(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C24 H24 0.9500 . ?
C24 C2 1.392(8) . ?
C5 C6 1.508(9) . ?
C5 C4 1.396(9) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.499(9) . ?
C17 H17 0.9500 . ?
C17 C18 1.397(9) . ?
C17 C16 1.391(9) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C20 C19 1.496(9) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C18 H18 0.9500 . ?
C18 C19 1.385(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C9 1.510(9) . ?
C16 C15 1.515(9) . ?
C16 C22 1.390(9) . ?
C4 H4 0.9500 . ?
C19 C21 1.377(10) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C21 H21 0.9500 . ?
C21 C22 1.390(9) . ?
C22 H22 0.9500 . ?
O10 C36 1.424(8) . ?
O10 C37 1.424(7) . ?
O9 C33 1.429(7) . ?
O9 C32 1.430(8) . ?
O7 H7 0.8400 . ?
O7 C25 1.343(8) . ?
O8 C25 1.203(7) . ?
O11 H11 0.8400 . ?
O11 C44 1.318(8) . ?
O12 C44 1.212(8) . ?
N4 H4A 1.0000 . ?
N4 C34 1.508(8) . ?
N4 C35 1.511(7) . ?
N4 C39 1.522(8) . ?
N3 H3A 1.0000 . ?
N3 C30 1.521(8) . ?
N3 C31 1.502(8) . ?
N3 C38 1.523(7) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 C33 1.515(9) . ?
C40 C41 1.391(9) . ?
C40 C39 1.500(9) . ?
C40 C46 1.394(9) . ?
C26 C25 1.481(9) . ?
C26 C27 1.397(8) . ?
C26 C48 1.376(9) . ?
C47 H47 0.9500 . ?
C47 C48 1.394(9) . ?
C47 C29 1.388(9) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.501(9) . ?
C42 H42 0.9500 . ?
C42 C41 1.395(9) . ?
C42 C43 1.381(10) . ?
C27 H27 0.9500 . ?
C27 C28 1.392(9) . ?
C41 H41 0.9500 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C48 H48 0.9500 . ?
C29 C28 1.395(9) . ?
C29 C30 1.512(9) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C28 H28 0.9500 . ?
C46 H46 0.9500 . ?
C46 C45 1.376(9) . ?
C43 C45 1.387(9) . ?
C43 C44 1.500(9) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C37 C38 1.494(9) . ?
C45 H45 0.9500 . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.510(8) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
O1W H1WA 1.01(3) . ?
O1W H1WB 1.00(3) . ?
O2W H2WA 0.995(7) . ?
O2W H2WB 1.00(3) . ?

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
C9 O3 C8 112.8(5) . . ?
C13 O4 C12 111.5(5) . . ?
C1 O2 H2 109.5 . . ?
C20 O5 H5 109.5 . . ?
C7 N1 H1 106.1 . . ?
C7 N1 C6 112.2(5) . . ?
C14 N1 H1 106.1 . . ?
C14 N1 C7 113.8(5) . . ?
C14 N1 C6 111.9(5) . . ?
C6 N1 H1 106.1 . . ?
C11 N2 H2A 105.9 . . ?
C11 N2 C10 114.0(5) . . ?
C11 N2 C15 112.4(5) . . ?
C10 N2 H2A 105.9 . . ?
C10 N2 C15 112.0(5) . . ?
C15 N2 H2A 105.9 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 120.0(6) . . ?
N1 C7 H7A 109.7 . . ?
N1 C7 H7B 109.7 . . ?
N1 C7 C8 109.6(5) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.7 . . ?
C8 C7 H7B 109.7 . . ?
C24 C23 H23 119.5 . . ?
C24 C23 C5 121.0(6) . . ?
C5 C23 H23 119.5 . . ?
O1 C1 O2 124.2(6) . . ?
O1 C1 C2 123.0(6) . . ?
O2 C1 C2 112.7(5) . . ?
O4 C13 H13A 110.2 . . ?
O4 C13 H13B 110.2 . . ?
O4 C13 C14 107.5(5) . . ?
H13A C13 H13B 108.5 . . ?
C14 C13 H13A 110.2 . . ?
C14 C13 H13B 110.2 . . ?
O3 C8 C7 106.3(5) . . ?
O3 C8 H8A 110.5 . . ?
O3 C8 H8B 110.5 . . ?
C7 C8 H8A 110.5 . . ?
C7 C8 H8B 110.5 . . ?
H8A C8 H8B 108.7 . . ?
C23 C24 H24 120.1 . . ?
C23 C24 C2 119.9(6) . . ?
C2 C24 H24 120.1 . . ?
C3 C2 C1 119.1(5) . . ?
C24 C2 C3 119.8(6) . . ?
C24 C2 C1 121.2(6) . . ?
C23 C5 C6 119.9(5) . . ?
C4 C5 C23 119.0(6) . . ?
C4 C5 C6 121.1(6) . . ?
O4 C12 H12A 109.8 . . ?
O4 C12 H12B 109.8 . . ?
O4 C12 C11 109.3(5) . . ?
H12A C12 H12B 108.3 . . ?
C11 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.4(6) . . ?
N1 C14 C13 112.2(5) . . ?
N1 C14 H14A 109.2 . . ?
N1 C14 H14B 109.2 . . ?
C13 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
N2 C11 C12 112.9(5) . . ?
N2 C11 H11A 109.0 . . ?
N2 C11 H11B 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
O5 C20 C19 112.2(6) . . ?
O6 C20 O5 125.7(6) . . ?
O6 C20 C19 122.1(7) . . ?
N1 C6 H6A 108.7 . . ?
N1 C6 H6B 108.7 . . ?
C5 C6 N1 114.2(5) . . ?
C5 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(6) . . ?
C19 C18 H18 119.9 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 C9 110.7(5) . . ?
H10A C10 H10B 108.1 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C17 C16 C15 120.2(6) . . ?
C22 C16 C17 118.8(6) . . ?
C22 C16 C15 121.0(6) . . ?
C3 C4 C5 120.5(6) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C18 C19 C20 120.5(6) . . ?
C21 C19 C20 120.2(6) . . ?
C21 C19 C18 119.2(6) . . ?
N2 C15 H15A 108.9 . . ?
N2 C15 H15B 108.9 . . ?
C16 C15 N2 113.5(5) . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
O3 C9 C10 106.7(5) . . ?
O3 C9 H9A 110.4 . . ?
O3 C9 H9B 110.4 . . ?
C10 C9 H9A 110.4 . . ?
C10 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
C19 C21 H21 119.5 . . ?
C19 C21 C22 121.0(6) . . ?
C22 C21 H21 119.5 . . ?
C16 C22 C21 120.3(6) . . ?
C16 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C36 O10 C37 113.5(5) . . ?
C33 O9 C32 111.0(4) . . ?
C25 O7 H7 109.5 . . ?
C44 O11 H11 109.5 . . ?
C34 N4 H4A 105.9 . . ?
C34 N4 C35 113.1(5) . . ?
C34 N4 C39 111.8(5) . . ?
C35 N4 H4A 105.9 . . ?
C35 N4 C39 113.3(5) . . ?
C39 N4 H4A 105.9 . . ?
C30 N3 H3A 106.3 . . ?
C30 N3 C38 111.6(5) . . ?
C31 N3 H3A 106.3 . . ?
C31 N3 C30 111.7(5) . . ?
C31 N3 C38 113.9(5) . . ?
C38 N3 H3A 106.3 . . ?
N4 C34 H34A 109.6 . . ?
N4 C34 H34B 109.6 . . ?
N4 C34 C33 110.4(5) . . ?
H34A C34 H34B 108.1 . . ?
C33 C34 H34A 109.6 . . ?
C33 C34 H34B 109.6 . . ?
C41 C40 C39 121.7(6) . . ?
C41 C40 C46 119.1(6) . . ?
C46 C40 C39 119.1(6) . . ?
C27 C26 C25 121.2(6) . . ?
C48 C26 C25 119.0(5) . . ?
C48 C26 C27 119.9(6) . . ?
C48 C47 H47 119.9 . . ?
C29 C47 H47 119.9 . . ?
C29 C47 C48 120.2(6) . . ?
O7 C25 C26 113.4(5) . . ?
O8 C25 O7 123.4(6) . . ?
O8 C25 C26 123.2(6) . . ?
N4 C35 H35A 109.5 . . ?
N4 C35 H35B 109.5 . . ?
H35A C35 H35B 108.1 . . ?
C36 C35 N4 110.8(5) . . ?
C36 C35 H35A 109.5 . . ?
C36 C35 H35B 109.5 . . ?
C41 C42 H42 120.0 . . ?
C43 C42 H42 120.0 . . ?
C43 C42 C41 119.9(6) . . ?
C26 C27 H27 120.2 . . ?
C28 C27 C26 119.7(6) . . ?
C28 C27 H27 120.2 . . ?
C40 C41 C42 120.1(6) . . ?
C40 C41 H41 120.0 . . ?
C42 C41 H41 120.0 . . ?
O10 C36 C35 106.8(5) . . ?
O10 C36 H36A 110.4 . . ?
O10 C36 H36B 110.4 . . ?
C35 C36 H36A 110.4 . . ?
C35 C36 H36B 110.4 . . ?
H36A C36 H36B 108.6 . . ?
N4 C39 H39A 108.8 . . ?
N4 C39 H39B 108.8 . . ?
C40 C39 N4 113.8(5) . . ?
C40 C39 H39A 108.8 . . ?
C40 C39 H39B 108.8 . . ?
H39A C39 H39B 107.7 . . ?
C26 C48 C47 120.5(6) . . ?
C26 C48 H48 119.7 . . ?
C47 C48 H48 119.7 . . ?
C47 C29 C28 119.3(6) . . ?
C47 C29 C30 121.3(6) . . ?
C28 C29 C30 119.4(5) . . ?
O9 C33 C34 108.2(5) . . ?
O9 C33 H33A 110.1 . . ?
O9 C33 H33B 110.1 . . ?
C34 C33 H33A 110.1 . . ?
C34 C33 H33B 110.1 . . ?
H33A C33 H33B 108.4 . . ?
C27 C28 C29 120.4(6) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C40 C46 H46 119.6 . . ?
C45 C46 C40 120.7(6) . . ?
C45 C46 H46 119.6 . . ?
C42 C43 C45 120.2(6) . . ?
C42 C43 C44 123.0(6) . . ?
C45 C43 C44 116.8(6) . . ?
O10 C37 H37A 110.6 . . ?
O10 C37 H37B 110.6 . . ?
O10 C37 C38 105.7(5) . . ?
H37A C37 H37B 108.7 . . ?
C38 C37 H37A 110.6 . . ?
C38 C37 H37B 110.6 . . ?
C46 C45 C43 119.9(6) . . ?
C46 C45 H45 120.0 . . ?
C43 C45 H45 120.0 . . ?
N3 C30 H30A 108.9 . . ?
N3 C30 H30B 108.9 . . ?
C29 C30 N3 113.2(5) . . ?
C29 C30 H30A 108.9 . . ?
C29 C30 H30B 108.9 . . ?
H30A C30 H30B 107.8 . . ?
O11 C44 C43 112.4(6) . . ?
O12 C44 O11 124.9(6) . . ?
O12 C44 C43 122.6(6) . . ?
N3 C31 H31A 108.9 . . ?
N3 C31 H31B 108.9 . . ?
N3 C31 C32 113.2(5) . . ?
H31A C31 H31B 107.8 . . ?
C32 C31 H31A 108.9 . . ?
C32 C31 H31B 108.9 . . ?
O9 C32 C31 109.2(5) . . ?
O9 C32 H32A 109.8 . . ?
O9 C32 H32B 109.8 . . ?
C31 C32 H32A 109.8 . . ?
C31 C32 H32B 109.8 . . ?
H32A C32 H32B 108.3 . . ?
N3 C38 H38A 109.7 . . ?
N3 C38 H38B 109.7 . . ?
C37 C38 N3 110.0(5) . . ?
C37 C38 H38A 109.7 . . ?
C37 C38 H38B 109.7 . . ?
H38A C38 H38B 108.2 . . ?
H1WA O1W H1WB 104(4) . . ?
H2WA O2W H2WB 109(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
O1W H1WA O6 1.01(3) 1.79(3) 2.781(7) 167(7) 3

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
O1 C1 C2 C3 15.8(9) . . . . ?
O1 C1 C2 C24 -164.1(6) . . . . ?
O4 C13 C14 N1 -59.9(6) . . . . ?
O4 C12 C11 N2 66.7(6) . . . . ?
O2 C1 C2 C3 -163.3(5) . . . . ?
O2 C1 C2 C24 16.7(8) . . . . ?
O5 C20 C19 C18 -12.8(8) . . . . ?
O5 C20 C19 C21 164.9(6) . . . . ?
O6 C20 C19 C18 169.3(6) . . . . ?
O6 C20 C19 C21 -13.1(9) . . . . ?
N1 C7 C8 O3 -68.4(6) . . . . ?
N2 C10 C9 O3 62.0(7) . . . . ?
C7 N1 C14 C13 -65.5(6) . . . . ?
C7 N1 C6 C5 -68.2(7) . . . . ?
C23 C24 C2 C3 -0.4(9) . . . . ?
C23 C24 C2 C1 179.5(6) . . . . ?
C23 C5 C6 N1 -86.8(7) . . . . ?
C23 C5 C4 C3 -0.1(9) . . . . ?
C13 O4 C12 C11 -170.6(5) . . . . ?
C8 O3 C9 C10 -170.3(5) . . . . ?
C24 C23 C5 C6 179.4(5) . . . . ?
C24 C23 C5 C4 -0.7(9) . . . . ?
C2 C3 C4 C5 0.6(9) . . . . ?
C5 C23 C24 C2 1.0(9) . . . . ?
C12 O4 C13 C14 162.7(5) . . . . ?
C17 C18 C19 C20 177.5(6) . . . . ?
C17 C18 C19 C21 -0.2(9) . . . . ?
C17 C16 C15 N2 77.5(7) . . . . ?
C17 C16 C22 C21 -2.8(9) . . . . ?
C14 N1 C7 C8 132.2(5) . . . . ?
C14 N1 C6 C5 61.1(7) . . . . ?
C11 N2 C10 C9 -125.3(6) . . . . ?
C11 N2 C15 C16 -67.1(7) . . . . ?
C20 C19 C21 C22 -176.5(6) . . . . ?
C6 N1 C7 C8 -99.6(6) . . . . ?
C6 N1 C14 C13 166.0(5) . . . . ?
C6 C5 C4 C3 179.8(5) . . . . ?
C18 C17 C16 C15 -177.8(6) . . . . ?
C18 C17 C16 C22 3.8(9) . . . . ?
C18 C19 C21 C22 1.2(9) . . . . ?
C10 N2 C11 C12 65.2(7) . . . . ?
C10 N2 C15 C16 62.8(7) . . . . ?
C16 C17 C18 C19 -2.3(9) . . . . ?
C4 C3 C2 C1 179.7(5) . . . . ?
C4 C3 C2 C24 -0.3(9) . . . . ?
C4 C5 C6 N1 93.3(7) . . . . ?
C19 C21 C22 C16 0.3(9) . . . . ?
C15 N2 C11 C12 -165.9(5) . . . . ?
C15 N2 C10 C9 105.7(6) . . . . ?
C15 C16 C22 C21 178.8(6) . . . . ?
C9 O3 C8 C7 175.4(5) . . . . ?
C22 C16 C15 N2 -104.2(7) . . . . ?
O10 C37 C38 N3 -65.2(6) . . . . ?
N4 C34 C33 O9 57.4(6) . . . . ?
N4 C35 C36 O10 61.3(7) . . . . ?
N3 C31 C32 O9 -64.3(7) . . . . ?
C34 N4 C35 C36 -132.4(6) . . . . ?
C34 N4 C39 C40 -75.3(6) . . . . ?
C40 C46 C45 C43 0.2(9) . . . . ?
C26 C27 C28 C29 1.7(9) . . . . ?
C47 C29 C28 C27 -2.1(9) . . . . ?
C47 C29 C30 N3 90.9(7) . . . . ?
C25 C26 C27 C28 179.1(5) . . . . ?
C25 C26 C48 C47 179.5(5) . . . . ?
C35 N4 C34 C33 71.0(6) . . . . ?
C35 N4 C39 C40 54.0(7) . . . . ?
C42 C43 C45 C46 2.0(9) . . . . ?
C42 C43 C44 O11 -7.0(9) . . . . ?
C42 C43 C44 O12 176.9(6) . . . . ?
C27 C26 C25 O7 20.2(8) . . . . ?
C27 C26 C25 O8 -159.1(6) . . . . ?
C27 C26 C48 C47 -1.6(9) . . . . ?
C41 C40 C39 N4 80.9(7) . . . . ?
C41 C40 C46 C45 -2.3(9) . . . . ?
C41 C42 C43 C45 -2.1(10) . . . . ?
C41 C42 C43 C44 178.9(6) . . . . ?
C36 O10 C37 C38 175.8(5) . . . . ?
C39 N4 C34 C33 -159.6(5) . . . . ?
C39 N4 C35 C36 99.0(6) . . . . ?
C39 C40 C41 C42 -178.2(6) . . . . ?
C39 C40 C46 C45 178.1(6) . . . . ?
C48 C26 C25 O7 -160.9(6) . . . . ?
C48 C26 C25 O8 19.8(9) . . . . ?
C48 C26 C27 C28 0.2(9) . . . . ?
C48 C47 C29 C28 0.7(9) . . . . ?
C48 C47 C29 C30 -179.6(5) . . . . ?
C29 C47 C48 C26 1.2(9) . . . . ?
C33 O9 C32 C31 169.1(5) . . . . ?
C28 C29 C30 N3 -89.3(7) . . . . ?
C46 C40 C41 C42 2.1(9) . . . . ?
C46 C40 C39 N4 -99.5(7) . . . . ?
C43 C42 C41 C40 0.0(10) . . . . ?
C37 O10 C36 C35 -173.5(5) . . . . ?
C45 C43 C44 O11 174.0(6) . . . . ?
C45 C43 C44 O12 -2.2(9) . . . . ?
C30 N3 C31 C32 168.6(5) . . . . ?
C30 N3 C38 C37 -104.1(6) . . . . ?
C30 C29 C28 C27 178.1(5) . . . . ?
C44 C43 C45 C46 -178.9(6) . . . . ?
C31 N3 C30 C29 58.9(7) . . . . ?
C31 N3 C38 C37 128.3(6) . . . . ?
C32 O9 C33 C34 -165.6(5) . . . . ?
C38 N3 C30 C29 -69.9(7) . . . . ?
C38 N3 C31 C32 -63.8(7) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a loop with paratone oil'
_olex2_submission_original_sample_id ligand1
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.72(9)
2 0.28(9)

