# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2059730'
loop_
_audit_author_name
_audit_author_address
'Laura Bereczki'
;Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2021-01-29 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
(S)-(1-cyclohexylethyl)ammonium (S)-2-(2-chlorophenyl)-2-hydroxyacetate
;
_chemical_name_common            
;
(S)-(1-cyclohexylethyl)ammonium (S)-2-chloromandelate'
;
_chemical_melting_point          410(1)
_chemical_formula_moiety         'C8 H18 N 1+, C8 H6 Cl O3 1-'
_chemical_formula_sum            'C16 H24 Cl N O3'
_chemical_formula_weight         313.81

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'
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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.8200(3)
_cell_length_b                   8.8363(3)
_cell_length_c                   26.1400(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1575.29(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    47931
_cell_measurement_theta_min      3.085
_cell_measurement_theta_max      27.470

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   0.97370
_exptl_transmission_factor_max   0.98470
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.41
_exptl_absorpt_coefficient_mu    0.252
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   
;
  NUMABS, Numerical Absorption correction Program (T.Higashi, 2011)
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  RAXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            50543
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.087
_diffrn_reflns_theta_max         27.471
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             50543
_reflns_number_gt                41935
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_cell_refinement       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_data_reduction        
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_structure_solution    
;
  Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.
;
_computing_publication_material  
;
C. F. Macrae, J. Appl. Cryst., 41, 466-470, 2008
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0357P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1211 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.041(10)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         50543
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.0772
_refine_ls_wR_factor_gt          0.0738
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.46659(11) 0.78710(8) 0.14083(3) 0.02854(18) Uani 1 1 d . . . . .
O2 O 0.6948(3) 0.5539(2) 0.23013(7) 0.0206(4) Uani 1 1 d . . . . .
O1 O 1.0183(3) 0.5546(2) 0.24465(6) 0.0230(4) Uani 1 1 d . . . . .
O3 O 1.0673(3) 0.81850(19) 0.19454(6) 0.0201(4) Uani 1 1 d . . . . .
H3 H 1.0575 0.8939 0.2126 0.030 Uiso 1 1 calc R U . . .
C4 C 0.6718(4) 0.7127(3) 0.10982(9) 0.0199(6) Uani 1 1 d . . . . .
C1 C 0.8661(4) 0.6065(3) 0.22488(9) 0.0161(6) Uani 1 1 d . . . . .
C3 C 0.8492(4) 0.6997(3) 0.13493(9) 0.0164(5) Uani 1 1 d . . . . .
C5 C 0.6483(5) 0.6706(3) 0.05917(10) 0.0289(8) Uani 1 1 d . . . . .
H5 H 0.5268 0.6793 0.0433 0.035 Uiso 1 1 calc R U . . .
C2 C 0.8831(4) 0.7477(3) 0.19037(9) 0.0155(6) Uani 1 1 d . . . . .
H2 H 0.7811 0.8202 0.2002 0.019 Uiso 1 1 calc R U . . .
C6 C 0.8076(5) 0.6155(3) 0.03257(11) 0.0347(8) Uani 1 1 d . . . . .
H6 H 0.7940 0.5879 -0.0016 0.042 Uiso 1 1 calc R U . . .
C8 C 1.0071(5) 0.6413(3) 0.10728(10) 0.0246(7) Uani 1 1 d . . . . .
H8 H 1.1277 0.6292 0.1234 0.030 Uiso 1 1 calc R U . . .
C7 C 0.9875(5) 0.6013(3) 0.05649(10) 0.0335(8) Uani 1 1 d . . . . .
H7 H 1.0950 0.5648 0.0384 0.040 Uiso 1 1 calc R U . . .
N1 N 0.6294(3) 0.2386(2) 0.22763(7) 0.0177(5) Uani 1 1 d . . . . .
H1A H 0.6592 0.3353 0.2331 0.027 Uiso 1 1 calc R U . . .
H1B H 0.7384 0.1833 0.2283 0.027 Uiso 1 1 calc R U . . .
H1C H 0.5479 0.2066 0.2519 0.027 Uiso 1 1 calc R U . . .
C11 C 0.6779(4) 0.2380(3) 0.13162(9) 0.0182(6) Uani 1 1 d . . . . .
H11 H 0.7270 0.3422 0.1309 0.022 Uiso 1 1 calc R U . . .
C12 C 0.8520(4) 0.1307(3) 0.13772(10) 0.0230(6) Uani 1 1 d . . . . .
H12A H 0.8029 0.0301 0.1453 0.028 Uiso 1 1 calc R U . . .
H12B H 0.9298 0.1635 0.1667 0.028 Uiso 1 1 calc R U . . .
C9 C 0.5319(4) 0.2225(3) 0.17599(8) 0.0187(6) Uani 1 1 d . . . . .
H9 H 0.4745 0.1210 0.1742 0.022 Uiso 1 1 calc R U . . .
C14 C 0.8667(4) 0.0811(3) 0.04325(10) 0.0249(7) Uani 1 1 d . . . . .
H14A H 0.9524 0.0790 0.0136 0.030 Uiso 1 1 calc R U . . .
H14B H 0.8094 -0.0186 0.0473 0.030 Uiso 1 1 calc R U . . .
C13 C 0.9846(5) 0.1217(3) 0.09071(10) 0.0268(7) Uani 1 1 d . . . . .
H13A H 1.0489 0.2184 0.0856 0.032 Uiso 1 1 calc R U . . .
H13B H 1.0851 0.0458 0.0963 0.032 Uiso 1 1 calc R U . . .
C15 C 0.7064(4) 0.1966(3) 0.03514(9) 0.0247(6) Uani 1 1 d . . . . .
H15A H 0.6311 0.1695 0.0050 0.030 Uiso 1 1 calc R U . . .
H15B H 0.7650 0.2951 0.0291 0.030 Uiso 1 1 calc R U . . .
C16 C 0.5690(4) 0.2063(3) 0.08131(9) 0.0232(6) Uani 1 1 d . . . . .
H16A H 0.4979 0.1117 0.0845 0.028 Uiso 1 1 calc R U . . .
H16B H 0.4739 0.2861 0.0755 0.028 Uiso 1 1 calc R U . . .
C10 C 0.3650(4) 0.3361(3) 0.17448(10) 0.0247(7) Uani 1 1 d . . . . .
H10A H 0.2887 0.3276 0.2052 0.037 Uiso 1 1 calc R U . . .
H10B H 0.2832 0.3158 0.1454 0.037 Uiso 1 1 calc R U . . .
H10C H 0.4176 0.4365 0.1719 0.037 Uiso 1 1 calc R U . . .


_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
Cl1 C4 1.746(3) . ?
O2 C1 1.265(3) . ?
O1 C1 1.247(3) . ?
O3 C2 1.408(3) . ?
O3 H3 0.8200 . ?
C4 C3 1.381(4) . ?
C4 C5 1.385(3) . ?
C1 C2 1.544(3) . ?
C3 C8 1.396(4) . ?
C3 C2 1.528(3) . ?
C5 C6 1.378(4) . ?
C5 H5 0.9300 . ?
C2 H2 0.9800 . ?
C6 C7 1.383(5) . ?
C6 H6 0.9300 . ?
C8 C7 1.381(3) . ?
C8 H8 0.9300 . ?
C7 H7 0.9300 . ?
N1 C9 1.511(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C11 C12 1.528(4) . ?
C11 C9 1.535(3) . ?
C11 C16 1.536(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.528(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C9 C10 1.518(4) . ?
C9 H9 0.9800 . ?
C14 C15 1.511(4) . ?
C14 C13 1.521(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 C16 1.530(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O3 H3 109.5 . . ?
C3 C4 C5 122.2(3) . . ?
C3 C4 Cl1 120.86(19) . . ?
C5 C4 Cl1 116.9(2) . . ?
O1 C1 O2 126.1(2) . . ?
O1 C1 C2 118.4(2) . . ?
O2 C1 C2 115.5(2) . . ?
C4 C3 C8 117.4(2) . . ?
C4 C3 C2 124.1(2) . . ?
C8 C3 C2 118.5(2) . . ?
C6 C5 C4 119.1(3) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
O3 C2 C3 109.4(2) . . ?
O3 C2 C1 112.4(2) . . ?
C3 C2 C1 108.57(19) . . ?
O3 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
C1 C2 H2 108.8 . . ?
C5 C6 C7 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C7 C8 C3 121.2(3) . . ?
C7 C8 H8 119.4 . . ?
C3 C8 H8 119.4 . . ?
C8 C7 C6 119.8(3) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C9 N1 H1A 109.5 . . ?
C9 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C9 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C12 C11 C9 111.7(2) . . ?
C12 C11 C16 110.6(2) . . ?
C9 C11 C16 108.5(2) . . ?
C12 C11 H11 108.6 . . ?
C9 C11 H11 108.6 . . ?
C16 C11 H11 108.6 . . ?
C11 C12 C13 114.1(2) . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
N1 C9 C10 106.92(19) . . ?
N1 C9 C11 112.4(2) . . ?
C10 C9 C11 114.1(2) . . ?
N1 C9 H9 107.7 . . ?
C10 C9 H9 107.7 . . ?
C11 C9 H9 107.7 . . ?
C15 C14 C13 109.7(2) . . ?
C15 C14 H14A 109.7 . . ?
C13 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C14 C13 C12 110.8(3) . . ?
C14 C13 H13A 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C14 C15 C16 111.7(2) . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 C11 112.9(2) . . ?
C15 C16 H16A 109.0 . . ?
C11 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C11 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
C5 C4 C3 C8 -0.2(4) . . . . ?
Cl1 C4 C3 C8 -179.00(18) . . . . ?
C5 C4 C3 C2 178.7(2) . . . . ?
Cl1 C4 C3 C2 -0.2(4) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
Cl1 C4 C5 C6 178.0(2) . . . . ?
C4 C3 C2 O3 -139.6(2) . . . . ?
C8 C3 C2 O3 39.2(3) . . . . ?
C4 C3 C2 C1 97.4(3) . . . . ?
C8 C3 C2 C1 -83.8(3) . . . . ?
O1 C1 C2 O3 -12.6(3) . . . . ?
O2 C1 C2 O3 167.6(2) . . . . ?
O1 C1 C2 C3 108.6(3) . . . . ?
O2 C1 C2 C3 -71.2(3) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C4 C3 C8 C7 1.3(4) . . . . ?
C2 C3 C8 C7 -177.6(2) . . . . ?
C3 C8 C7 C6 -1.5(4) . . . . ?
C5 C6 C7 C8 0.4(4) . . . . ?
C9 C11 C12 C13 170.4(2) . . . . ?
C16 C11 C12 C13 49.4(3) . . . . ?
C12 C11 C9 N1 52.9(3) . . . . ?
C16 C11 C9 N1 175.1(2) . . . . ?
C12 C11 C9 C10 174.9(2) . . . . ?
C16 C11 C9 C10 -62.9(3) . . . . ?
C15 C14 C13 C12 57.6(3) . . . . ?
C11 C12 C13 C14 -54.5(3) . . . . ?
C13 C14 C15 C16 -58.4(3) . . . . ?
C14 C15 C16 C11 55.0(3) . . . . ?
C12 C11 C16 C15 -49.0(3) . . . . ?
C9 C11 C16 C15 -171.9(2) . . . . ?

_refine_diff_density_max         0.406
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.042



####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2059732'
loop_
_audit_author_name
_audit_author_address
'Laura Bereczki'
;Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2021-01-29 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
(S)-(1-cyclohexylethyl)ammonium (R,S)-2-(2-chlorophenyl)-2-hydroxyacetate
;
_chemical_name_common            
;
(S)-(1-cyclohexylethyl)ammonium (R,S)-2-chloromandelate
;
_chemical_melting_point          420(1)
_chemical_formula_moiety         'C8 H18 N 1+, C8 H6 Cl O3 1-'
_chemical_formula_sum            'C16 H24 Cl N O3'
_chemical_formula_weight         313.81

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.6370(2)
_cell_length_b                   25.3851(6)
_cell_length_c                   13.5859(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.277(6)
_cell_angle_gamma                90
_cell_volume                     3323.56(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    24104
_cell_measurement_theta_min      3.255
_cell_measurement_theta_max      72.300

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   0.972722
_exptl_transmission_factor_max   0.992144
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    2.113
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   
;
  NUMABS, Numerical Absorption correction Program (T.Higashi, 2011)
;
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  RAXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            25816
_diffrn_reflns_av_unetI/netI     0.1044
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.253
_diffrn_reflns_theta_max         68.238
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_point_group_measured_fraction_full 0.888
_reflns_number_total             25816
_reflns_number_gt                19821
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_max     0.779
_reflns_Friedel_fraction_full    0.781

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_cell_refinement       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_data_reduction        
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_structure_solution    
;
  Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.
;
_computing_publication_material  
;
C. F. Macrae, J. Appl. Cryst., 41, 466-470, 2008
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1862P)²+5.1105P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2072 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.189(14)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         25816
_refine_ls_number_parameters     835
_refine_ls_number_restraints     235
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.1070
_refine_ls_wR_factor_ref         0.3010
_refine_ls_wR_factor_gt          0.2808
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1C Cl 0.7896(4) 0.16510(15) 0.8284(2) 0.0668(12) Uani 1 1 d . . . . .
Cl1D Cl 0.6076(4) 0.16228(15) 0.3279(2) 0.0584(10) Uani 1 1 d . . . . .
Cl1B Cl 0.1069(4) 0.34407(18) 0.9110(3) 0.0725(13) Uani 1 1 d . . . . .
Cl1A Cl 0.3195(5) 0.32761(19) 1.4150(3) 0.0850(15) Uani 1 1 d . . . . .
O2D O 0.7950(9) 0.2266(4) 0.4819(6) 0.046(2) Uani 1 1 d . . . . .
O2A O 0.0635(9) 0.2675(4) 1.2633(6) 0.047(2) Uani 1 1 d . . . . .
O1A O 0.0906(9) 0.2514(3) 1.1025(5) 0.042(2) Uani 1 1 d . . . . .
O1C O 0.5984(9) 0.2483(4) 1.1383(6) 0.046(2) Uani 1 1 d . . . . .
O1D O 0.7616(9) 0.2402(4) 0.6419(7) 0.051(3) Uani 1 1 d . . . . .
O2B O 0.2959(9) 0.2774(4) 0.7616(6) 0.045(2) Uani 1 1 d . . . . .
O1B O 0.2568(9) 0.2567(4) 0.6037(6) 0.049(2) Uani 1 1 d D . . . .
O3A O 0.3448(9) 0.2960(4) 1.1015(6) 0.049(2) Uani 1 1 d . . . . .
H3A H 0.426517 0.288798 1.111769 0.073 Uiso 1 1 calc R U . . .
O2C O 0.5586(9) 0.2265(4) 0.9825(5) 0.043(2) Uani 1 1 d . . . . .
N1A N 0.7752(11) 0.2763(4) 1.2973(7) 0.042(3) Uani 1 1 d . . . . .
H1A1 H 0.861330 0.275812 1.273939 0.063 Uiso 1 1 calc R U . . .
H1A2 H 0.715957 0.267595 1.249466 0.063 Uiso 1 1 calc R U . . .
H1A3 H 0.768126 0.253215 1.346353 0.063 Uiso 1 1 calc R U . . .
O3B O -0.0016(9) 0.2925(3) 0.6101(6) 0.043(2) Uani 1 1 d . . . . .
H3B H -0.034188 0.262627 0.611149 0.064 Uiso 1 1 calc R U . . .
N1B N 0.5763(11) 0.2725(4) 0.7949(7) 0.040(3) Uani 1 1 d . . . . .
H1B1 H 0.644032 0.260980 0.756129 0.060 Uiso 1 1 calc R U . . .
H1B2 H 0.497466 0.274204 0.760627 0.060 Uiso 1 1 calc R U . . .
H1B3 H 0.565967 0.250539 0.845288 0.060 Uiso 1 1 calc R U . . .
O3D O 0.4980(9) 0.2097(4) 0.6321(5) 0.046(2) Uani 1 1 d D . . . .
H3D H 0.427853 0.226128 0.617071 0.070 Uiso 1 1 calc DR U . . .
O3C O 0.8470(9) 0.1986(4) 1.1405(6) 0.049(3) Uani 1 1 d . . . . .
H3C H 0.928307 0.205963 1.129395 0.074 Uiso 1 1 calc R U . . .
N1C N 0.2695(11) 0.2250(4) 0.9434(7) 0.043(3) Uani 1 1 d . . . . .
H1C1 H 0.353563 0.223613 0.970732 0.065 Uiso 1 1 calc R U . . .
H1C2 H 0.208492 0.236187 0.987636 0.065 Uiso 1 1 calc R U . . .
H1C3 H 0.270767 0.247149 0.892597 0.065 Uiso 1 1 calc R U . . .
N1D N 0.0786(11) 0.2212(4) 0.4533(7) 0.045(3) Uani 1 1 d . . . . .
H1D1 H 0.131982 0.233296 0.501976 0.067 Uiso 1 1 calc R U . . .
H1D2 H -0.009064 0.219654 0.473485 0.067 Uiso 1 1 calc R U . . .
H1D3 H 0.084421 0.242802 0.401862 0.067 Uiso 1 1 calc R U . . .
C1A C 0.1366(14) 0.2702(5) 1.1825(9) 0.043(3) Uani 1 1 d . . . . .
C1D C 0.7228(13) 0.2243(5) 0.5590(8) 0.036(3) Uani 1 1 d . . . . .
C2A C 0.2683(15) 0.2941(6) 1.1943(9) 0.047(4) Uani 1 1 d . . . . .
H2A H 0.322522 0.275445 1.244566 0.057 Uiso 1 1 calc R U . . .
C9C C 0.2296(14) 0.1722(5) 0.9089(8) 0.040(3) Uani 1 1 d . . . . .
H9C H 0.148100 0.176596 0.866302 0.048 Uiso 1 1 calc R U . . .
C1B C 0.2216(14) 0.2778(5) 0.6851(9) 0.038(3) Uani 1 1 d . . . . .
C9A C 0.7425(13) 0.3292(5) 1.3335(9) 0.042(3) Uani 1 1 d . . . . .
H9A H 0.665132 0.325321 1.379441 0.051 Uiso 1 1 calc R U . . .
C11A C 0.6891(14) 0.3644(5) 1.2468(9) 0.046(3) Uani 1 1 d . . . . .
H11A H 0.610618 0.345931 1.216204 0.055 Uiso 1 1 calc R U . . .
C3D C 0.5926(14) 0.1434(5) 0.5262(10) 0.046(4) Uani 1 1 d . . . . .
C1C C 0.6288(15) 0.2262(5) 1.0577(8) 0.044(4) Uani 1 1 d . . . . .
C3B C 0.0933(13) 0.3622(5) 0.7102(9) 0.040(3) Uani 1 1 d . . . . .
C2B C 0.0744(14) 0.3008(5) 0.6937(8) 0.041(3) Uani 1 1 d . . . . .
H2B H 0.026957 0.285191 0.750346 0.049 Uiso 1 1 calc R U . . .
C3A C 0.2450(14) 0.3540(6) 1.2259(10) 0.051(4) Uani 1 1 d . . . . .
C3C C 0.7423(13) 0.1416(5) 1.0193(9) 0.043(3) Uani 1 1 d . . . . .
C2D C 0.5781(13) 0.2011(5) 0.5481(8) 0.042(3) Uani 1 1 d . U . . .
H2D H 0.532018 0.218026 0.491988 0.050 Uiso 1 1 calc R U . . .
C2C C 0.7714(13) 0.1977(5) 1.0508(9) 0.041(3) Uani 1 1 d . . . . .
H2C H 0.826887 0.214874 0.999812 0.049 Uiso 1 1 calc R U . . .
C9B C 0.6130(14) 0.3270(5) 0.8333(9) 0.047(4) Uani 1 1 d . . . . .
H9B H 0.560287 0.333308 0.893646 0.056 Uiso 1 1 calc R U . . .
C8C C 0.7013(14) 0.1034(6) 1.0918(10) 0.048(4) Uani 1 1 d . . . . .
H8C H 0.694279 0.113793 1.157197 0.057 Uiso 1 1 calc R U . . .
C4D C 0.6105(14) 0.1224(5) 0.4320(10) 0.048(4) Uani 1 1 d . . . . .
C11C C 0.1856(15) 0.1372(5) 0.9955(10) 0.051(4) Uani 1 1 d . . . . .
H11C H 0.111355 0.156021 1.029759 0.061 Uiso 1 1 calc R U . . .
C9D C 0.1255(14) 0.1683(5) 0.4247(9) 0.048(3) Uani 1 1 d D . . . .
H9D H 0.061422 0.151218 0.378433 0.057 Uiso 1 1 calc R U . A 1
C4B C 0.1065(16) 0.3836(7) 0.8046(11) 0.067(5) Uani 1 1 d . . . . .
C8A C 0.2039(14) 0.3883(6) 1.1619(11) 0.052(4) Uani 1 1 d . . . . .
H8A H 0.196591 0.377371 1.096773 0.063 Uiso 1 1 calc R U . . .
C11B C 0.5695(16) 0.3683(5) 0.7564(10) 0.052(4) Uani 1 1 d . U . . .
H11B H 0.471141 0.362942 0.740865 0.063 Uiso 1 1 calc R U . . .
C13C C 0.2517(18) 0.0956(6) 1.1568(10) 0.064(5) Uani 1 1 d . . . . .
H13A H 0.180000 0.114976 1.191285 0.076 Uiso 1 1 calc R U . . .
H13B H 0.327733 0.089473 1.202415 0.076 Uiso 1 1 calc R U . . .
C4C C 0.7423(14) 0.1225(7) 0.9230(10) 0.053(4) Uani 1 1 d . . . . .
C5D C 0.6319(16) 0.0696(7) 0.4165(12) 0.065(5) Uani 1 1 d . . . . .
H5D H 0.647776 0.056710 0.353439 0.078 Uiso 1 1 calc R U . . .
C10A C 0.8604(15) 0.3508(5) 1.3905(9) 0.047(3) Uani 1 1 d . . . . .
H10A H 0.896001 0.324255 1.434074 0.070 Uiso 1 1 calc R U . . .
H10B H 0.829504 0.380536 1.428269 0.070 Uiso 1 1 calc R U . . .
H10C H 0.932128 0.361790 1.346225 0.070 Uiso 1 1 calc R U . . .
C14C C 0.1919(19) 0.0414(7) 1.1203(11) 0.070(5) Uani 1 1 d . . . . .
H14A H 0.265653 0.020621 1.091228 0.083 Uiso 1 1 calc R U . . .
H14B H 0.155106 0.021892 1.175774 0.083 Uiso 1 1 calc R U . . .
C16C C 0.1223(15) 0.0837(5) 0.9598(9) 0.049(4) Uani 1 1 d . . . . .
H16A H 0.042087 0.090576 0.918360 0.059 Uiso 1 1 calc R U . . .
H16B H 0.190315 0.064947 0.920762 0.059 Uiso 1 1 calc R U . . .
C13A C 0.7468(18) 0.4065(6) 1.0844(11) 0.067(5) Uani 1 1 d . . . . .
H13C H 0.676507 0.387339 1.047649 0.080 Uiso 1 1 calc R U . . .
H13D H 0.822493 0.414235 1.039912 0.080 Uiso 1 1 calc R U . . .
C7D C 0.6120(16) 0.0549(6) 0.5890(12) 0.063(5) Uani 1 1 d . . . . .
H7D H 0.613922 0.031909 0.642242 0.076 Uiso 1 1 calc R U . . .
C8D C 0.5922(15) 0.1070(6) 0.6039(11) 0.054(4) Uani 1 1 d . . . . .
H8D H 0.577814 0.119132 0.667627 0.065 Uiso 1 1 calc R U . . .
C12A C 0.7995(16) 0.3724(6) 1.1664(9) 0.058(4) Uani 1 1 d . . . . .
H12A H 0.881236 0.388565 1.195447 0.070 Uiso 1 1 calc R U . . .
H12B H 0.826452 0.338412 1.140091 0.070 Uiso 1 1 calc R U . . .
C4A C 0.2630(16) 0.3701(7) 1.3191(11) 0.066(5) Uani 1 1 d . . . . .
C7B C 0.1066(16) 0.4485(6) 0.6464(12) 0.062(5) Uani 1 1 d . . . . .
H7B H 0.109287 0.471274 0.592814 0.074 Uiso 1 1 calc R U . . .
C16B C 0.5854(19) 0.4223(6) 0.8013(11) 0.065(4) Uani 1 1 d . U . . .
H16C H 0.529734 0.424196 0.860476 0.078 Uiso 1 1 calc R U . . .
H16D H 0.681628 0.427458 0.820255 0.078 Uiso 1 1 calc R U . . .
C16A C 0.6350(15) 0.4181(5) 1.2836(10) 0.050(4) Uani 1 1 d . . . . .
H16I H 0.563657 0.412493 1.332588 0.059 Uiso 1 1 calc R U . . .
H16J H 0.710350 0.437455 1.314416 0.059 Uiso 1 1 calc R U . . .
C7C C 0.6731(16) 0.0535(7) 1.0679(12) 0.065(5) Uani 1 1 d . . . . .
H7C H 0.657875 0.029126 1.117791 0.078 Uiso 1 1 calc R U . . .
C14A C 0.6842(18) 0.4587(5) 1.1217(11) 0.060(4) Uani 1 1 d . . . . .
H14C H 0.757795 0.480336 1.149168 0.072 Uiso 1 1 calc R U . . .
H14D H 0.644237 0.477668 1.066339 0.072 Uiso 1 1 calc R U . . .
C6C C 0.6660(17) 0.0377(6) 0.9736(12) 0.062(4) Uani 1 1 d . . . . .
H6C H 0.636598 0.003868 0.957515 0.074 Uiso 1 1 calc R U . . .
C8B C 0.0921(16) 0.3941(6) 0.6329(12) 0.061(5) Uani 1 1 d . . . . .
H8B H 0.081724 0.380309 0.569813 0.074 Uiso 1 1 calc R U . . .
C10D C 0.2683(15) 0.1735(6) 0.3840(11) 0.060(4) Uani 1 1 d . . . . .
H10D H 0.270389 0.201715 0.337108 0.090 Uiso 1 1 calc R U . . .
H10E H 0.294166 0.141159 0.352286 0.090 Uiso 1 1 calc R U . . .
H10F H 0.332414 0.180824 0.436595 0.090 Uiso 1 1 calc R U . . .
C6D C 0.6293(18) 0.0362(7) 0.4959(15) 0.080(6) Uani 1 1 d . . . . .
H6D H 0.639524 0.000180 0.485932 0.096 Uiso 1 1 calc R U . . .
C15A C 0.5748(16) 0.4508(6) 1.1980(10) 0.061(4) Uani 1 1 d . . . . .
H15A H 0.495894 0.432618 1.169275 0.073 Uiso 1 1 calc R U . . .
H15B H 0.543297 0.484699 1.222231 0.073 Uiso 1 1 calc R U . . .
C12C C 0.3016(16) 0.1272(6) 1.0722(9) 0.054(4) Uani 1 1 d . . . . .
H12C H 0.377779 0.108817 1.040899 0.065 Uiso 1 1 calc R U . . .
H12D H 0.336453 0.160742 1.096048 0.065 Uiso 1 1 calc R U . . .
C5B C 0.124(2) 0.4372(7) 0.8214(15) 0.083(6) Uani 1 1 d . . . . .
H5B H 0.139128 0.451048 0.883848 0.100 Uiso 1 1 calc R U . . .
C7A C 0.1701(16) 0.4395(7) 1.1824(14) 0.071(5) Uani 1 1 d . . . . .
H7A H 0.140504 0.462103 1.132606 0.086 Uiso 1 1 calc R U . . .
C10C C 0.3452(15) 0.1501(6) 0.8453(9) 0.058(4) Uani 1 1 d . . . . .
H10G H 0.376008 0.176719 0.800209 0.087 Uiso 1 1 calc R U . . .
H10H H 0.311136 0.120299 0.809142 0.087 Uiso 1 1 calc R U . . .
H10I H 0.421295 0.139422 0.886541 0.087 Uiso 1 1 calc R U . . .
C6B C 0.1166(18) 0.4674(7) 0.7408(17) 0.088(7) Uani 1 1 d . . . . .
H6B H 0.118595 0.503698 0.749323 0.105 Uiso 1 1 calc R U . . .
C5C C 0.7028(18) 0.0723(7) 0.9027(12) 0.069(5) Uani 1 1 d . . . . .
H5C H 0.700942 0.061306 0.837380 0.082 Uiso 1 1 calc R U . . .
C5A C 0.235(2) 0.4207(8) 1.3493(14) 0.092(7) Uani 1 1 d . . . . .
H5A H 0.251933 0.430999 1.413989 0.111 Uiso 1 1 calc R U . . .
C15C C 0.0797(15) 0.0500(6) 1.0460(10) 0.057(4) Uani 1 1 d . . . . .
H15C H 0.001455 0.066585 1.078258 0.068 Uiso 1 1 calc R U . . .
H15D H 0.048938 0.016095 1.021437 0.068 Uiso 1 1 calc R U . . .
C14B C 0.6305(19) 0.4626(6) 0.6375(11) 0.073(5) Uani 1 1 d D U . . .
H14I H 0.607852 0.491585 0.593786 0.087 Uiso 1 1 calc R U . B 3
H14J H 0.728653 0.464293 0.653363 0.087 Uiso 1 1 calc R U . B 3
C15B C 0.5425(17) 0.4659(6) 0.7329(11) 0.066(4) Uani 1 1 d D U . . .
H15E H 0.556974 0.499741 0.764567 0.079 Uiso 1 1 calc R U . . .
H15F H 0.444773 0.462604 0.716793 0.079 Uiso 1 1 calc R U . . .
C12B C 0.650(2) 0.3646(6) 0.6621(11) 0.085(6) Uani 1 1 d D U . . .
H12E H 0.636273 0.330288 0.632326 0.102 Uiso 1 1 calc R U . C 3
H12F H 0.748233 0.369209 0.675300 0.102 Uiso 1 1 calc R U . C 3
C6A C 0.1809(18) 0.4570(7) 1.2788(15) 0.075(6) Uani 1 1 d . . . . .
H6A H 0.153893 0.490852 1.296768 0.091 Uiso 1 1 calc R U . . .
C10B C 0.7575(14) 0.3255(6) 0.8579(9) 0.053(4) Uani 1 1 d . . . . .
H10J H 0.811247 0.323809 0.798719 0.080 Uiso 1 1 calc R U . . .
H10K H 0.776288 0.295005 0.897611 0.080 Uiso 1 1 calc R U . . .
H10L H 0.781872 0.356694 0.894039 0.080 Uiso 1 1 calc R U . . .
C11D C 0.157(3) 0.1338(10) 0.5151(18) 0.039(6) Uani 0.502(19) 1 d D U P D 1
H11D H 0.247999 0.149061 0.530200 0.047 Uiso 0.502(19) 1 calc R U P D 1
C12D C 0.105(5) 0.1385(13) 0.605(2) 0.076(11) Uani 0.502(19) 1 d D U P D 1
H12G H 0.045386 0.169398 0.602941 0.091 Uiso 0.502(19) 1 calc R U P D 1
H12H H 0.182369 0.147689 0.647387 0.091 Uiso 0.502(19) 1 calc R U P D 1
C16D C 0.206(3) 0.0792(9) 0.499(2) 0.048(8) Uani 0.502(19) 1 d D U P D 1
H16E H 0.294769 0.080823 0.465236 0.058 Uiso 0.502(19) 1 calc R U P D 1
H16F H 0.141147 0.061710 0.454892 0.058 Uiso 0.502(19) 1 calc R U P D 1
C13D C 0.019(5) 0.0951(18) 0.665(3) 0.062(12) Uani 0.502(19) 1 d D U P D 1
H13E H -0.078830 0.096937 0.647031 0.075 Uiso 0.502(19) 1 calc R U P D 1
H13F H 0.027610 0.101125 0.734952 0.075 Uiso 0.502(19) 1 calc R U P D 1
C14D C 0.082(4) 0.0376(19) 0.636(3) 0.060(11) Uani 0.502(19) 1 d D U P D 1
H14E H 0.087244 0.015566 0.694228 0.072 Uiso 0.502(19) 1 calc R U P D 1
H14F H 0.021410 0.020374 0.588492 0.072 Uiso 0.502(19) 1 calc R U P D 1
C15D C 0.224(3) 0.0447(12) 0.593(2) 0.068(10) Uani 0.502(19) 1 d D U P D 1
H15G H 0.263906 0.010774 0.576122 0.082 Uiso 0.502(19) 1 calc R U P D 1
H15H H 0.284877 0.062030 0.639849 0.082 Uiso 0.502(19) 1 calc R U P D 1
C15E C 0.044(4) 0.0340(12) 0.533(2) 0.076(9) Uani 0.498(19) 1 d D U P D 2
H15I H 0.051622 -0.001312 0.506387 0.091 Uiso 0.498(19) 1 calc R U P D 2
H15J H -0.053316 0.042093 0.542420 0.091 Uiso 0.498(19) 1 calc R U P D 2
C16E C 0.109(4) 0.0732(10) 0.464(2) 0.060(8) Uani 0.498(19) 1 d D U P D 2
H16G H 0.208474 0.067801 0.462098 0.072 Uiso 0.498(19) 1 calc R U P D 2
H16H H 0.072298 0.068082 0.398053 0.072 Uiso 0.498(19) 1 calc R U P D 2
C11E C 0.079(4) 0.1278(10) 0.497(2) 0.051(8) Uani 0.498(19) 1 d D U P D 2
H11E H 0.163383 0.130306 0.537211 0.061 Uiso 0.498(19) 1 calc R U P D 2
C12E C -0.003(4) 0.1236(13) 0.575(2) 0.056(8) Uani 0.498(19) 1 d D U P D 2
H12I H -0.088981 0.107186 0.553674 0.067 Uiso 0.498(19) 1 calc R U P D 2
H12J H -0.025318 0.158871 0.597183 0.067 Uiso 0.498(19) 1 calc R U P D 2
C13E C 0.057(5) 0.0917(18) 0.664(4) 0.067(12) Uani 0.498(19) 1 d D U P D 2
H13G H -0.017649 0.084697 0.710153 0.081 Uiso 0.498(19) 1 calc R U P D 2
H13H H 0.126120 0.112779 0.697530 0.081 Uiso 0.498(19) 1 calc R U P D 2
C14E C 0.123(5) 0.0381(19) 0.631(3) 0.066(11) Uani 0.498(19) 1 d D U P D 2
H14G H 0.222843 0.040613 0.622403 0.079 Uiso 0.498(19) 1 calc R U P D 2
H14H H 0.101553 0.009401 0.675781 0.079 Uiso 0.498(19) 1 calc R U P D 2
C13B C 0.596(7) 0.4101(11) 0.589(2) 0.086(12) Uani 0.72(13) 1 d D U P E 3
H13I H 0.641474 0.407337 0.525439 0.104 Uiso 0.72(13) 1 calc R U P E 3
H13J H 0.496338 0.407014 0.578331 0.104 Uiso 0.72(13) 1 calc R U P E 3
C13F C 0.65(2) 0.417(3) 0.601(9) 0.092(19) Uani 0.28(13) 1 d D U P E 4
H13K H 0.738036 0.418607 0.567182 0.110 Uiso 0.28(13) 1 calc R U P E 4
H13L H 0.579252 0.412873 0.550051 0.110 Uiso 0.28(13) 1 calc R U P E 4


_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
Cl1C C4C 1.743(15) . ?
Cl1D C4D 1.740(14) . ?
Cl1B C4B 1.759(18) . ?
Cl1A C4A 1.776(19) . ?
O2D C1D 1.261(12) . ?
O2A C1A 1.310(13) . ?
O1A C1A 1.265(15) . ?
O1C C1C 1.266(13) . ?
O1D C1D 1.252(13) . ?
O2B C1B 1.260(14) . ?
O1B C1B 1.277(12) . ?
O3A C2A 1.464(13) . ?
O2C C1C 1.222(15) . ?
N1A C9A 1.465(15) . ?
O3B C2B 1.364(14) . ?
N1B C9B 1.518(16) . ?
O3D C2D 1.398(11) . ?
O3C C2C 1.417(15) . ?
N1C C9C 1.469(15) . ?
N1D C9D 1.470(16) . ?
C1A C2A 1.415(19) . ?
C1D C2D 1.521(17) . ?
C2A C3A 1.597(19) . ?
C9C C10C 1.520(15) . ?
C9C C11C 1.536(16) . ?
C1B C2B 1.538(17) . ?
C9A C10A 1.478(18) . ?
C9A C11A 1.564(17) . ?
C11A C12A 1.542(16) . ?
C11A C16A 1.546(18) . ?
C3D C4D 1.397(17) . ?
C3D C8D 1.402(17) . ?
C3D C2D 1.501(18) . ?
C1C C2C 1.556(19) . ?
C3B C8B 1.325(18) . ?
C3B C4B 1.399(18) . ?
C3B C2B 1.587(18) . ?
C3A C8A 1.291(18) . ?
C3A C4A 1.341(19) . ?
C3C C4C 1.396(17) . ?
C3C C8C 1.438(17) . ?
C3C C2C 1.513(17) . ?
C9B C10B 1.431(18) . ?
C9B C11B 1.538(18) . ?
C8C C7C 1.33(2) . ?
C4D C5D 1.37(2) . ?
C11C C12C 1.55(2) . ?
C11C C16C 1.564(18) . ?
C9D C10D 1.492(18) . ?
C9D C11E 1.50(2) . ?
C9D C11D 1.54(2) . ?
C4B C5B 1.39(2) . ?
C8A C7A 1.37(2) . ?
C11B C12B 1.503(18) . ?
C11B C16B 1.507(19) . ?
C13C C12C 1.483(18) . ?
C13C C14C 1.57(2) . ?
C4C C5C 1.36(2) . ?
C5D C6D 1.37(2) . ?
C14C C15C 1.49(2) . ?
C16C C15C 1.509(16) . ?
C13A C12A 1.50(2) . ?
C13A C14A 1.54(2) . ?
C7D C8D 1.351(19) . ?
C7D C6D 1.36(2) . ?
C4A C5A 1.37(2) . ?
C7B C6B 1.37(2) . ?
C7B C8B 1.401(19) . ?
C16B C15B 1.50(2) . ?
C16A C15A 1.539(19) . ?
C7C C6C 1.34(2) . ?
C14A C15A 1.496(19) . ?
C6C C5C 1.35(2) . ?
C5B C6B 1.34(2) . ?
C7A C6A 1.39(2) . ?
C5A C6A 1.43(3) . ?
C14B C13F 1.27(11) . ?
C14B C13B 1.53(4) . ?
C14B C15B 1.554(18) . ?
C12B C13F 1.57(4) . ?
C12B C13B 1.61(3) . ?
C11D C12D 1.33(3) . ?
C11D C16D 1.48(3) . ?
C12D C13D 1.60(4) . ?
C16D C15D 1.56(3) . ?
C13D C14D 1.63(3) . ?
C14D C15D 1.50(3) . ?
C15E C16E 1.50(3) . ?
C15E C14E 1.54(4) . ?
C16E C11E 1.49(3) . ?
C11E C12E 1.32(3) . ?
C12E C13E 1.57(4) . ?
C13E C14E 1.57(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
O1A C1A O2A 120.9(12) . . ?
O1A C1A C2A 124.7(11) . . ?
O2A C1A C2A 114.4(12) . . ?
O1D C1D O2D 124.6(12) . . ?
O1D C1D C2D 118.8(9) . . ?
O2D C1D C2D 116.6(10) . . ?
C1A C2A O3A 111.8(11) . . ?
C1A C2A C3A 108.2(11) . . ?
O3A C2A C3A 105.8(10) . . ?
N1C C9C C10C 109.1(10) . . ?
N1C C9C C11C 110.9(9) . . ?
C10C C9C C11C 115.3(11) . . ?
O2B C1B O1B 123.9(12) . . ?
O2B C1B C2B 117.5(10) . . ?
O1B C1B C2B 118.3(12) . . ?
N1A C9A C10A 110.6(11) . . ?
N1A C9A C11A 109.9(10) . . ?
C10A C9A C11A 115.6(11) . . ?
C12A C11A C16A 110.3(11) . . ?
C12A C11A C9A 112.5(11) . . ?
C16A C11A C9A 111.8(10) . . ?
C4D C3D C8D 116.1(13) . . ?
C4D C3D C2D 124.4(11) . . ?
C8D C3D C2D 119.5(12) . . ?
O2C C1C O1C 126.2(13) . . ?
O2C C1C C2C 116.0(10) . . ?
O1C C1C C2C 117.8(12) . . ?
C8B C3B C4B 119.5(14) . . ?
C8B C3B C2B 119.2(12) . . ?
C4B C3B C2B 121.3(13) . . ?
O3B C2B C1B 111.7(10) . . ?
O3B C2B C3B 109.3(11) . . ?
C1B C2B C3B 106.1(10) . . ?
C8A C3A C4A 117.9(16) . . ?
C8A C3A C2A 120.3(14) . . ?
C4A C3A C2A 121.8(14) . . ?
C4C C3C C8C 114.1(13) . . ?
C4C C3C C2C 126.3(13) . . ?
C8C C3C C2C 119.5(11) . . ?
O3D C2D C3D 111.5(10) . . ?
O3D C2D C1D 111.7(10) . . ?
C3D C2D C1D 108.1(10) . . ?
O3C C2C C3C 110.7(11) . . ?
O3C C2C C1C 113.0(10) . . ?
C3C C2C C1C 107.0(10) . . ?
C10B C9B N1B 106.3(11) . . ?
C10B C9B C11B 116.0(11) . . ?
N1B C9B C11B 109.0(11) . . ?
C7C C8C C3C 122.0(13) . . ?
C5D C4D C3D 122.1(14) . . ?
C5D C4D Cl1D 116.4(12) . . ?
C3D C4D Cl1D 121.5(10) . . ?
C9C C11C C12C 114.2(12) . . ?
C9C C11C C16C 112.0(11) . . ?
C12C C11C C16C 110.3(11) . . ?
N1D C9D C10D 107.7(11) . . ?
N1D C9D C11E 111.0(12) . . ?
C10D C9D C11E 125.9(17) . . ?
N1D C9D C11D 111.7(13) . . ?
C10D C9D C11D 99.6(15) . . ?
C5B C4B C3B 122.7(17) . . ?
C5B C4B Cl1B 115.1(13) . . ?
C3B C4B Cl1B 122.2(13) . . ?
C3A C8A C7A 125.2(17) . . ?
C12B C11B C16B 110.5(13) . . ?
C12B C11B C9B 113.3(12) . . ?
C16B C11B C9B 108.6(12) . . ?
C12C C13C C14C 110.4(12) . . ?
C5C C4C C3C 121.1(14) . . ?
C5C C4C Cl1C 120.4(12) . . ?
C3C C4C Cl1C 118.5(13) . . ?
C6D C5D C4D 118.6(15) . . ?
C15C C14C C13C 110.3(13) . . ?
C15C C16C C11C 111.0(11) . . ?
C12A C13A C14A 112.6(12) . . ?
C8D C7D C6D 119.9(16) . . ?
C7D C8D C3D 122.0(14) . . ?
C13A C12A C11A 111.7(13) . . ?
C3A C4A C5A 122.9(19) . . ?
C3A C4A Cl1A 123.1(13) . . ?
C5A C4A Cl1A 114.1(14) . . ?
C6B C7B C8B 118.3(16) . . ?
C15B C16B C11B 113.1(13) . . ?
C15A C16A C11A 111.0(11) . . ?
C8C C7C C6C 121.6(15) . . ?
C15A C14A C13A 112.9(12) . . ?
C7C C6C C5C 118.2(16) . . ?
C3B C8B C7B 119.8(16) . . ?
C7D C6D C5D 121.2(16) . . ?
C14A C15A C16A 109.4(13) . . ?
C13C C12C C11C 112.0(13) . . ?
C6B C5B C4B 114.9(17) . . ?
C8A C7A C6A 118.6(18) . . ?
C5B C6B C7B 124.7(17) . . ?
C6C C5C C4C 122.6(15) . . ?
C4A C5A C6A 118.3(18) . . ?
C14C C15C C16C 114.2(13) . . ?
C13F C14B C15B 117(5) . . ?
C13B C14B C15B 107(2) . . ?
C16B C15B C14B 109.0(13) . . ?
C11B C12B C13F 113(5) . . ?
C11B C12B C13B 108(2) . . ?
C7A C6A C5A 116.9(16) . . ?
C12D C11D C16D 110(2) . . ?
C12D C11D C9D 127(2) . . ?
C16D C11D C9D 118(2) . . ?
C11D C12D C13D 127(3) . . ?
C11D C16D C15D 116(2) . . ?
C12D C13D C14D 108(3) . . ?
C15D C14D C13D 109(3) . . ?
C14D C15D C16D 107(3) . . ?
C16E C15E C14E 107(3) . . ?
C11E C16E C15E 110(2) . . ?
C12E C11E C16E 107(2) . . ?
C12E C11E C9D 140(2) . . ?
C16E C11E C9D 112.2(18) . . ?
C11E C12E C13E 116(3) . . ?
C12E C13E C14E 112(4) . . ?
C15E C14E C13E 96(4) . . ?
C14B C13B C12B 107(3) . . ?
C14B C13F C12B 124(8) . . ?

_refine_diff_density_max         1.429
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.104



####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2059734'
loop_
_audit_author_name
_audit_author_address
'Laura Bereczki'
;Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2021-01-29 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
(R)-(1-cyclohexylethyl)ammonium (S)-2-(4-chlorophenyl)-2-hydroxyacetate
;
_chemical_name_common            
;
(R)-(1-cyclohexylethyl)ammonium (S)-4-chloromandelate'
;
_chemical_melting_point          426(1)
_chemical_formula_moiety         'C8 H18 N 1+, C8 H6 Cl O3 1-'
_chemical_formula_sum            'C16 H24 Cl N O3'
_chemical_formula_weight         313.81

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.4640(6)
_cell_length_b                   10.4673(7)
_cell_length_c                   29.8915(16)
_cell_angle_alpha                90
_cell_angle_beta                 96.843(3)
_cell_angle_gamma                90
_cell_volume                     3250.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    5466
_cell_measurement_theta_min      6.910
_cell_measurement_theta_max      66.380

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   0.372680
_exptl_transmission_factor_max   0.840704
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    2.161
_shelx_estimated_absorpt_T_min   0.411
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.373
_exptl_absorpt_correction_T_max  0.841
_exptl_absorpt_process_details   
;
  NUMABS, Numerical Absorption correction Program (T.Higashi, 2003)
;
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  RAXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            6812
_diffrn_reflns_av_unetI/netI     0.0803
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         6.536
_diffrn_reflns_theta_max         50.435
_diffrn_reflns_theta_full        50.435
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6812
_reflns_number_gt                6308
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_cell_refinement       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_data_reduction        
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_structure_solution    
;
Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.
;
_computing_publication_material  
;
C. F. Macrae, J. Appl. Cryst., 41, 466-470, 2008
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+16.4355P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2166 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.036(11)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         6812
_refine_ls_number_parameters     725
_refine_ls_number_restraints     607
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0908
_refine_ls_wR_factor_ref         0.1879
_refine_ls_wR_factor_gt          0.1842
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1A Cl 0.4232(6) 0.8398(4) 0.31537(16) 0.0551(15) Uani 1 1 d . . . . .
O1A O 0.6354(10) 0.4667(10) 0.4933(3) 0.030(3) Uani 1 1 d . U . . .
O2A O 0.5096(10) 0.3174(9) 0.4571(3) 0.024(3) Uani 1 1 d . U . . .
O3A O 0.2988(11) 0.4325(10) 0.4794(3) 0.026(3) Uani 1 1 d D U . . .
C1A C 0.5285(17) 0.4239(16) 0.4771(5) 0.027(2) Uani 1 1 d . U . . .
C2A C 0.4102(15) 0.5107(16) 0.4797(5) 0.0284(19) Uani 1 1 d . U . . .
H2A H 0.4226 0.5611 0.5083 0.040 Uiso 1 1 calc R U . . .
C3A C 0.4055(10) 0.6012(9) 0.4399(3) 0.0287(18) Uani 1 1 d G U . . .
C4A C 0.5012(9) 0.6929(10) 0.4390(3) 0.0308(19) Uani 1 1 d G U . . .
H4A H 0.5638 0.7041 0.4645 0.046 Uiso 1 1 calc R U . . .
C5A C 0.5052(9) 0.7684(9) 0.4010(3) 0.0315(19) Uani 1 1 d G U . . .
H5A H 0.5706 0.8311 0.4004 0.047 Uiso 1 1 calc R U . . .
C6A C 0.4136(11) 0.7522(10) 0.3637(3) 0.031(2) Uani 1 1 d G U . . .
C7A C 0.3179(9) 0.6604(10) 0.3646(3) 0.0309(19) Uani 1 1 d G U . . .
H7A H 0.2552 0.6493 0.3392 0.046 Uiso 1 1 calc R U . . .
C8A C 0.3138(9) 0.5849(9) 0.4027(3) 0.0301(19) Uani 1 1 d G U . . .
H8A H 0.2484 0.5222 0.4032 0.045 Uiso 1 1 calc R U . . .
Cl1B Cl -0.1012(6) 0.9369(5) 0.30418(16) 0.0573(16) Uani 1 1 d . . . . .
O1B O -0.0412(10) 0.7135(10) 0.5227(3) 0.029(3) Uani 1 1 d . U . . .
O2B O 0.1170(10) 0.5790(10) 0.5106(3) 0.026(3) Uani 1 1 d D U . . .
O3B O -0.0401(10) 0.4494(10) 0.4461(3) 0.026(3) Uani 1 1 d D U . . .
H3OB H 0.0165 0.4206 0.4719 0.034 Uiso 1 1 d DR U . . .
C1B C 0.0058(17) 0.6242(16) 0.5007(6) 0.029(2) Uani 1 1 d . U . . .
C2B C -0.0817(16) 0.5700(16) 0.4612(5) 0.0310(19) Uani 1 1 d . U . . .
H2B H -0.1706 0.5608 0.4699 0.043 Uiso 1 1 calc R U . . .
C3B C -0.0851(11) 0.6638(9) 0.4212(3) 0.0313(18) Uani 1 1 d G U . . .
C4B C -0.1382(11) 0.7846(10) 0.4247(3) 0.0332(19) Uani 1 1 d G U . . .
H4B H -0.1706 0.8095 0.4517 0.050 Uiso 1 1 calc R U . . .
C5B C -0.1440(11) 0.8689(8) 0.3885(3) 0.0341(19) Uani 1 1 d G U . . .
H5B H -0.1803 0.9514 0.3909 0.051 Uiso 1 1 calc R U . . .
C6B C -0.0967(11) 0.8324(9) 0.3489(3) 0.0336(19) Uani 1 1 d G U . . .
C7B C -0.0435(10) 0.7116(10) 0.3455(3) 0.0330(19) Uani 1 1 d G U . . .
H7B H -0.0112 0.6867 0.3184 0.049 Uiso 1 1 calc R U . . .
C8B C -0.0378(10) 0.6273(8) 0.3816(3) 0.0324(19) Uani 1 1 d G U . . .
H8B H -0.0014 0.5448 0.3792 0.049 Uiso 1 1 calc R U . . .
Cl1C Cl 1.0189(4) 0.0198(4) 0.20142(14) 0.0379(12) Uani 1 1 d . . . . .
O1C O 1.1333(10) 0.3941(10) 0.0271(3) 0.028(3) Uani 1 1 d . U . . .
O2C O 1.0280(9) 0.5687(9) 0.0462(3) 0.020(2) Uani 1 1 d . U . . .
O3C O 0.8060(10) 0.4448(11) 0.0417(3) 0.026(3) Uani 1 1 d D U . . .
C1C C 1.0367(16) 0.4510(16) 0.0371(5) 0.025(2) Uani 1 1 d . U . . .
C2C C 0.9188(15) 0.3681(16) 0.0397(5) 0.0262(18) Uani 1 1 d . U . . .
H2C H 0.9053 0.3150 0.0117 0.037 Uiso 1 1 calc R U . . .
C3C C 0.9413(10) 0.2774(8) 0.0803(3) 0.0264(17) Uani 1 1 d G U . . .
C4C C 0.9177(10) 0.3204(7) 0.1225(3) 0.0266(17) Uani 1 1 d G U . . .
H4C H 0.8855 0.4043 0.1259 0.040 Uiso 1 1 calc R U . . .
C5C C 0.9413(10) 0.2408(9) 0.1598(2) 0.0274(18) Uani 1 1 d G U . . .
H5C H 0.9252 0.2702 0.1887 0.041 Uiso 1 1 calc R U . . .
C6C C 0.9884(11) 0.1181(9) 0.1548(3) 0.0272(18) Uani 1 1 d G U . . .
C7C C 1.0120(10) 0.0751(7) 0.1126(3) 0.0274(18) Uani 1 1 d G U . . .
H7C H 1.0443 -0.0088 0.1092 0.041 Uiso 1 1 calc R U . . .
C8C C 0.9885(10) 0.1547(9) 0.0753(2) 0.0269(17) Uani 1 1 d G U . . .
H8C H 1.0046 0.1253 0.0465 0.040 Uiso 1 1 calc R U . . .
Cl1D Cl 0.4826(4) 0.0492(4) 0.23353(13) 0.0362(11) Uani 1 1 d . . . . .
O1D O 0.6289(9) 0.2591(10) 0.0166(3) 0.023(3) Uani 1 1 d D U . . .
O2D O 0.4495(10) 0.1430(10) 0.0025(3) 0.026(3) Uani 1 1 d . U . . .
O3D O 0.5039(10) 0.4391(10) 0.0608(3) 0.025(3) Uani 1 1 d D U . . .
H3OD H 0.5088 0.4481 0.0277 0.033 Uiso 1 1 d DR U . . .
C1D C 0.5145(15) 0.2334(15) 0.0215(5) 0.022(2) Uani 1 1 d . U . . .
C2D C 0.4451(16) 0.3157(14) 0.0539(5) 0.0237(17) Uani 1 1 d . U . . .
H2D H 0.3525 0.3256 0.0417 0.033 Uiso 1 1 calc R U . . .
C3D C 0.4558(9) 0.2507(9) 0.0995(2) 0.0241(16) Uani 1 1 d G U . . .
C4D C 0.5758(8) 0.2289(10) 0.1236(3) 0.0254(17) Uani 1 1 d G U . . .
H4D H 0.6516 0.2565 0.1118 0.038 Uiso 1 1 calc R U . . .
C5D C 0.5850(7) 0.1669(10) 0.1650(3) 0.0255(17) Uani 1 1 d G U . . .
H5D H 0.6671 0.1521 0.1814 0.038 Uiso 1 1 calc R U . . .
C6D C 0.4742(9) 0.1266(9) 0.1823(2) 0.0259(18) Uani 1 1 d G U . . .
C7D C 0.3542(8) 0.1484(10) 0.1582(3) 0.0251(17) Uani 1 1 d G U . . .
H7D H 0.2785 0.1208 0.1700 0.038 Uiso 1 1 calc R U . . .
C8D C 0.3450(7) 0.2104(10) 0.1168(3) 0.0248(17) Uani 1 1 d G U . . .
H8D H 0.2630 0.2252 0.1003 0.037 Uiso 1 1 calc R U . . .
N1A N 0.2869(13) 0.1627(12) 0.4478(4) 0.028(3) Uani 1 1 d . U . . .
H1A1 H 0.2107 0.1982 0.4531 0.042 Uiso 1 1 calc R U . . .
H1A2 H 0.3483 0.2245 0.4489 0.042 Uiso 1 1 calc R U . . .
H1A3 H 0.3107 0.1026 0.4692 0.042 Uiso 1 1 calc R U . . .
C9A C 0.2719(17) 0.1016(15) 0.4024(5) 0.029(3) Uani 1 1 d . U . . .
H9A H 0.3572 0.0634 0.3981 0.041 Uiso 1 1 calc R U . . .
C10A C 0.1795(16) -0.0063(15) 0.4029(5) 0.031(3) Uani 1 1 d . U . . .
H10A H 0.2101 -0.0656 0.4272 0.044 Uiso 1 1 calc R U . . .
H10B H 0.1725 -0.0511 0.3740 0.044 Uiso 1 1 calc R U . . .
H10C H 0.0948 0.0270 0.4080 0.044 Uiso 1 1 calc R U . . .
C11A C 0.2419(16) 0.2008(16) 0.3655(5) 0.0261(19) Uani 1 1 d . U . . .
H11A H 0.3049 0.2720 0.3724 0.039 Uiso 1 1 calc R U . . .
C12A C 0.1100(15) 0.2587(16) 0.3642(5) 0.0258(19) Uani 1 1 d . U . . .
H12A H 0.1020 0.3002 0.3935 0.039 Uiso 1 1 calc R U . . .
H12B H 0.0448 0.1899 0.3598 0.039 Uiso 1 1 calc R U . . .
C13A C 0.0822(16) 0.3580(16) 0.3262(5) 0.027(2) Uani 1 1 d . U . . .
H13A H -0.0077 0.3881 0.3254 0.040 Uiso 1 1 calc R U . . .
H13B H 0.1397 0.4325 0.3328 0.040 Uiso 1 1 calc R U . . .
C14A C 0.1022(15) 0.3032(15) 0.2807(5) 0.0266(19) Uani 1 1 d . U . . .
H14A H 0.0915 0.3716 0.2577 0.040 Uiso 1 1 calc R U . . .
H14B H 0.0367 0.2366 0.2721 0.040 Uiso 1 1 calc R U . . .
C15A C 0.2371(16) 0.2450(16) 0.2821(5) 0.027(2) Uani 1 1 d . U . . .
H15A H 0.2451 0.2031 0.2528 0.041 Uiso 1 1 calc R U . . .
H15B H 0.3019 0.3142 0.2862 0.041 Uiso 1 1 calc R U . . .
C16A C 0.2656(16) 0.1472(15) 0.3199(5) 0.027(2) Uani 1 1 d . U . . .
H16A H 0.2104 0.0711 0.3131 0.040 Uiso 1 1 calc R U . . .
H16B H 0.3564 0.1195 0.3213 0.040 Uiso 1 1 calc R U . . .
N1B N 0.7556(12) 0.2658(11) 0.4328(4) 0.021(3) Uani 1 1 d . U . . .
H1B1 H 0.8127 0.3318 0.4348 0.032 Uiso 1 1 calc R U . . .
H1B2 H 0.7856 0.2030 0.4524 0.032 Uiso 1 1 calc R U . . .
H1B3 H 0.6783 0.2940 0.4399 0.032 Uiso 1 1 calc R U . . .
C9B C 0.7399(15) 0.2143(15) 0.3858(5) 0.022(3) Uani 1 1 d . U . . .
H9B H 0.8201 0.1663 0.3813 0.031 Uiso 1 1 calc R U . . .
C10B C 0.6291(15) 0.1184(15) 0.3832(5) 0.027(3) Uani 1 1 d . U . . .
H10D H 0.6485 0.0525 0.4063 0.037 Uiso 1 1 calc R U . . .
H10E H 0.6182 0.0784 0.3533 0.037 Uiso 1 1 calc R U . . .
H10F H 0.5496 0.1627 0.3882 0.037 Uiso 1 1 calc R U . . .
C11B C 0.7229(17) 0.3199(17) 0.3511(5) 0.034(2) Uani 1 1 d . U . . .
H11B H 0.7964 0.3804 0.3585 0.051 Uiso 1 1 calc R U . . .
C12B C 0.6007(17) 0.3983(16) 0.3501(6) 0.035(2) Uani 1 1 d . U . . .
H12C H 0.5983 0.4395 0.3797 0.053 Uiso 1 1 calc R U . . .
H12D H 0.5252 0.3410 0.3445 0.053 Uiso 1 1 calc R U . . .
C13B C 0.5923(17) 0.5009(16) 0.3135(5) 0.036(2) Uani 1 1 d . U . . .
H13C H 0.5099 0.5477 0.3131 0.054 Uiso 1 1 calc R U . . .
H13D H 0.6633 0.5629 0.3205 0.054 Uiso 1 1 calc R U . . .
C14B C 0.6006(17) 0.4433(17) 0.2673(6) 0.036(2) Uani 1 1 d . U . . .
H14C H 0.5961 0.5120 0.2444 0.054 Uiso 1 1 calc R U . . .
H14D H 0.5271 0.3847 0.2594 0.054 Uiso 1 1 calc R U . . .
C15B C 0.7263(17) 0.3706(17) 0.2677(6) 0.035(2) Uani 1 1 d . U . . .
H15C H 0.7996 0.4303 0.2737 0.053 Uiso 1 1 calc R U . . .
H15D H 0.7305 0.3307 0.2379 0.053 Uiso 1 1 calc R U . . .
C16B C 0.7353(18) 0.2669(17) 0.3042(5) 0.035(2) Uani 1 1 d . U . . .
H16C H 0.6665 0.2031 0.2963 0.052 Uiso 1 1 calc R U . . .
H16D H 0.8191 0.2225 0.3048 0.052 Uiso 1 1 calc R U . . .
N1C N 0.7964(12) 0.7264(11) 0.0374(4) 0.019(3) Uani 1 1 d . U . . .
H1C1 H 0.7212 0.6853 0.0281 0.028 Uiso 1 1 calc R U . . .
H1C2 H 0.8574 0.6681 0.0478 0.028 Uiso 1 1 calc R U . . .
H1C3 H 0.8229 0.7700 0.0139 0.028 Uiso 1 1 calc R U . . .
C9C C 0.7759(15) 0.8181(14) 0.0744(5) 0.020(3) Uani 1 1 d . U . . .
H9C H 0.8589 0.8646 0.0828 0.028 Uiso 1 1 calc R U . . .
C10C C 0.6770(14) 0.9153(14) 0.0564(5) 0.021(3) Uani 1 1 d . U . . .
H10G H 0.6994 0.9496 0.0279 0.029 Uiso 1 1 calc R U . . .
H10H H 0.6750 0.9849 0.0783 0.029 Uiso 1 1 calc R U . . .
H10I H 0.5921 0.8746 0.0515 0.029 Uiso 1 1 calc R U . . .
C11C C 0.7455(16) 0.7426(16) 0.1166(5) 0.029(2) Uani 1 1 d . U . . .
H11C H 0.6755 0.6797 0.1072 0.044 Uiso 1 1 calc R U . . .
C12C C 0.6977(17) 0.8363(16) 0.1512(5) 0.030(2) Uani 1 1 d . U . . .
H12E H 0.7621 0.9049 0.1583 0.045 Uiso 1 1 calc R U . . .
H12F H 0.6160 0.8763 0.1381 0.045 Uiso 1 1 calc R U . . .
C13C C 0.6766(17) 0.7657(16) 0.1945(5) 0.031(2) Uani 1 1 d . U . . .
H13E H 0.6522 0.8282 0.2168 0.046 Uiso 1 1 calc R U . . .
H13F H 0.6041 0.7052 0.1878 0.046 Uiso 1 1 calc R U . . .
C14C C 0.7923(16) 0.6938(16) 0.2146(5) 0.030(2) Uani 1 1 d . U . . .
H14E H 0.7708 0.6456 0.2412 0.045 Uiso 1 1 calc R U . . .
H14F H 0.8617 0.7551 0.2250 0.045 Uiso 1 1 calc R U . . .
C15C C 0.8413(17) 0.6003(16) 0.1807(5) 0.030(2) Uani 1 1 d . U . . .
H15E H 0.9225 0.5604 0.1943 0.045 Uiso 1 1 calc R U . . .
H15F H 0.7770 0.5318 0.1734 0.045 Uiso 1 1 calc R U . . .
C16C C 0.8640(16) 0.6698(16) 0.1383(5) 0.029(2) Uani 1 1 d . U . . .
H16E H 0.8904 0.6072 0.1163 0.044 Uiso 1 1 calc R U . . .
H16F H 0.9358 0.7309 0.1454 0.044 Uiso 1 1 calc R U . . .
N1D N 0.2957(12) 0.6368(12) 0.0570(4) 0.027(3) Uani 1 1 d . U . . .
H1D1 H 0.2100 0.6196 0.0518 0.040 Uiso 1 1 calc R U . . .
H1D2 H 0.3397 0.5631 0.0639 0.040 Uiso 1 1 calc R U . . .
H1D3 H 0.3225 0.6718 0.0318 0.040 Uiso 1 1 calc R U . . .
C9D C 0.3204(17) 0.7296(16) 0.0957(5) 0.029(3) Uani 1 1 d . U . . .
H9D H 0.4154 0.7360 0.1047 0.040 Uiso 1 1 calc R U . . .
C10D C 0.2704(16) 0.8584(15) 0.0782(5) 0.030(3) Uani 1 1 d . U . . .
H10J H 0.3099 0.8805 0.0511 0.042 Uiso 1 1 calc R U . . .
H10K H 0.2924 0.9235 0.1014 0.042 Uiso 1 1 calc R U . . .
H10L H 0.1767 0.8543 0.0709 0.042 Uiso 1 1 calc R U . . .
C11D C 0.2566(17) 0.6796(16) 0.1357(5) 0.030(2) Uani 1 1 d . U . . .
H11D H 0.1627 0.6697 0.1253 0.045 Uiso 1 1 calc R U . . .
C12D C 0.2689(17) 0.7698(16) 0.1756(5) 0.031(2) Uani 1 1 d . U . . .
H12G H 0.3614 0.7874 0.1846 0.046 Uiso 1 1 calc R U . . .
H12H H 0.2272 0.8518 0.1660 0.046 Uiso 1 1 calc R U . . .
C13D C 0.2122(17) 0.7233(16) 0.2156(5) 0.031(2) Uani 1 1 d . U . . .
H13G H 0.1174 0.7192 0.2086 0.047 Uiso 1 1 calc R U . . .
H13H H 0.2327 0.7841 0.2408 0.047 Uiso 1 1 calc R U . . .
C14D C 0.2627(17) 0.5935(15) 0.2297(5) 0.032(2) Uani 1 1 d . U . . .
H14G H 0.2162 0.5618 0.2544 0.048 Uiso 1 1 calc R U . . .
H14H H 0.3549 0.6009 0.2415 0.048 Uiso 1 1 calc R U . . .
C15D C 0.2484(17) 0.4971(16) 0.1916(5) 0.032(2) Uani 1 1 d . U . . .
H15G H 0.1559 0.4793 0.1827 0.048 Uiso 1 1 calc R U . . .
H15H H 0.2908 0.4161 0.2020 0.048 Uiso 1 1 calc R U . . .
C16D C 0.3087(16) 0.5471(16) 0.1506(5) 0.031(2) Uani 1 1 d . U . . .
H16G H 0.2902 0.4863 0.1253 0.047 Uiso 1 1 calc R U . . .
H16H H 0.4032 0.5520 0.1582 0.047 Uiso 1 1 calc R U . . .
H3OC H 0.723(7) 0.406(15) 0.038(10) 0.24(18) Uiso 1 1 d D . . . .
H3OA H 0.24(2) 0.499(18) 0.477(4) 0.3(2) 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
Cl1A C6A 1.726(8) . ?
O1A C1A 1.248(19) . ?
O2A C1A 1.270(18) . ?
O3A C2A 1.424(18) . ?
O3A H3OA 0.950(8) . ?
C1A C2A 1.54(2) . ?
C2A C3A 1.517(17) . ?
C2A H2A 1.0000 . ?
C3A C4A 1.3900 . ?
C3A C8A 1.3900 . ?
C4A C5A 1.3900 . ?
C4A H4A 0.9500 . ?
C5A C6A 1.3900 . ?
C5A H5A 0.9500 . ?
C6A C7A 1.3900 . ?
C7A C8A 1.3900 . ?
C7A H7A 0.9500 . ?
C8A H8A 0.9500 . ?
Cl1B C6B 1.725(8) . ?
O1B C1B 1.274(19) . ?
O2B C1B 1.26(2) . ?
O3B C2B 1.425(19) . ?
O3B H3OB 0.9645 . ?
C1B C2B 1.52(2) . ?
C2B C3B 1.544(17) . ?
C2B H2B 1.0000 . ?
C3B C4B 1.3900 . ?
C3B C8B 1.3900 . ?
C4B C5B 1.3900 . ?
C4B H4B 0.9500 . ?
C5B C6B 1.3900 . ?
C5B H5B 0.9500 . ?
C6B C7B 1.3900 . ?
C7B C8B 1.3900 . ?
C7B H7B 0.9500 . ?
C8B H8B 0.9500 . ?
Cl1C C6C 1.730(8) . ?
O1C C1C 1.239(19) . ?
O2C C1C 1.267(18) . ?
O3C C2C 1.435(19) . ?
O3C H3OC 0.950(8) . ?
C1C C2C 1.52(2) . ?
C2C C3C 1.536(17) . ?
C2C H2C 1.0000 . ?
C3C C4C 1.3900 . ?
C3C C8C 1.3900 . ?
C4C C5C 1.3900 . ?
C4C H4C 0.9500 . ?
C5C C6C 1.3900 . ?
C5C H5C 0.9500 . ?
C6C C7C 1.3900 . ?
C7C C8C 1.3900 . ?
C7C H7C 0.9500 . ?
C8C H8C 0.9500 . ?
Cl1D C6D 1.727(7) . ?
O1D C1D 1.252(18) . ?
O2D C1D 1.261(17) . ?
O3D C2D 1.435(18) . ?
O3D H3OD 0.9997 . ?
C1D C2D 1.54(2) . ?
C2D C3D 1.516(16) . ?
C2D H2D 1.0000 . ?
C3D C4D 1.3900 . ?
C3D C8D 1.3900 . ?
C4D C5D 1.3900 . ?
C4D H4D 0.9500 . ?
C5D C6D 1.3900 . ?
C5D H5D 0.9500 . ?
C6D C7D 1.3900 . ?
C7D C8D 1.3900 . ?
C7D H7D 0.9500 . ?
C8D H8D 0.9500 . ?
N1A C9A 1.493(19) . ?
N1A H1A1 0.9100 . ?
N1A H1A2 0.9100 . ?
N1A H1A3 0.9100 . ?
C9A C10A 1.49(2) . ?
C9A C11A 1.52(2) . ?
C9A H9A 1.0000 . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C11A C12A 1.50(2) . ?
C11A C16A 1.52(2) . ?
C11A H11A 1.0000 . ?
C12A C13A 1.54(2) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C13A C14A 1.51(2) . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C14A C15A 1.53(2) . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
C15A C16A 1.53(2) . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C16A H16A 0.9900 . ?
C16A H16B 0.9900 . ?
N1B C9B 1.495(18) . ?
N1B H1B1 0.9100 . ?
N1B H1B2 0.9100 . ?
N1B H1B3 0.9100 . ?
C9B C11B 1.51(2) . ?
C9B C10B 1.53(2) . ?
C9B H9B 1.0000 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11B C12B 1.52(2) . ?
C11B C16B 1.53(2) . ?
C11B H11B 1.0000 . ?
C12B C13B 1.53(2) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B C14B 1.52(2) . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C14B C15B 1.52(2) . ?
C14B H14C 0.9900 . ?
C14B H14D 0.9900 . ?
C15B C16B 1.53(2) . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C16B H16C 0.9900 . ?
C16B H16D 0.9900 . ?
N1C C9C 1.499(18) . ?
N1C H1C1 0.9100 . ?
N1C H1C2 0.9100 . ?
N1C H1C3 0.9100 . ?
C9C C10C 1.50(2) . ?
C9C C11C 1.55(2) . ?
C9C H9C 1.0000 . ?
C10C H10G 0.9800 . ?
C10C H10H 0.9800 . ?
C10C H10I 0.9800 . ?
C11C C16C 1.53(2) . ?
C11C C12C 1.55(2) . ?
C11C H11C 1.0000 . ?
C12C C13C 1.53(2) . ?
C12C H12E 0.9900 . ?
C12C H12F 0.9900 . ?
C13C C14C 1.49(2) . ?
C13C H13E 0.9900 . ?
C13C H13F 0.9900 . ?
C14C C15C 1.54(2) . ?
C14C H14E 0.9900 . ?
C14C H14F 0.9900 . ?
C15C C16C 1.50(2) . ?
C15C H15E 0.9900 . ?
C15C H15F 0.9900 . ?
C16C H16E 0.9900 . ?
C16C H16F 0.9900 . ?
N1D C9D 1.509(19) . ?
N1D H1D1 0.9100 . ?
N1D H1D2 0.9100 . ?
N1D H1D3 0.9100 . ?
C9D C10D 1.52(2) . ?
C9D C11D 1.53(2) . ?
C9D H9D 1.0000 . ?
C10D H10J 0.9800 . ?
C10D H10K 0.9800 . ?
C10D H10L 0.9800 . ?
C11D C12D 1.52(2) . ?
C11D C16D 1.54(2) . ?
C11D H11D 1.0000 . ?
C12D C13D 1.48(2) . ?
C12D H12G 0.9900 . ?
C12D H12H 0.9900 . ?
C13D C14D 1.50(2) . ?
C13D H13G 0.9900 . ?
C13D H13H 0.9900 . ?
C14D C15D 1.52(2) . ?
C14D H14G 0.9900 . ?
C14D H14H 0.9900 . ?
C15D C16D 1.54(2) . ?
C15D H15G 0.9900 . ?
C15D H15H 0.9900 . ?
C16D H16G 0.9900 . ?
C16D H16H 0.9900 . ?

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
C2A O3A H3OA 98(10) . . ?
O1A C1A O2A 125.5(15) . . ?
O1A C1A C2A 117.1(14) . . ?
O2A C1A C2A 117.3(15) . . ?
O3A C2A C3A 113.9(12) . . ?
O3A C2A C1A 108.8(13) . . ?
C3A C2A C1A 106.2(12) . . ?
O3A C2A H2A 109.3 . . ?
C3A C2A H2A 109.3 . . ?
C1A C2A H2A 109.3 . . ?
C4A C3A C8A 120.0 . . ?
C4A C3A C2A 119.3(9) . . ?
C8A C3A C2A 120.4(9) . . ?
C3A C4A C5A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C6A C5A C4A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C7A C6A C5A 120.0 . . ?
C7A C6A Cl1A 119.8(6) . . ?
C5A C6A Cl1A 120.1(6) . . ?
C6A C7A C8A 120.0 . . ?
C6A C7A H7A 120.0 . . ?
C8A C7A H7A 120.0 . . ?
C7A C8A C3A 120.0 . . ?
C7A C8A H8A 120.0 . . ?
C3A C8A H8A 120.0 . . ?
C2B O3B H3OB 101.8 . . ?
O2B C1B O1B 123.9(15) . . ?
O2B C1B C2B 119.9(15) . . ?
O1B C1B C2B 116.2(15) . . ?
O3B C2B C1B 113.5(14) . . ?
O3B C2B C3B 107.3(11) . . ?
C1B C2B C3B 108.7(13) . . ?
O3B C2B H2B 109.1 . . ?
C1B C2B H2B 109.1 . . ?
C3B C2B H2B 109.1 . . ?
C4B C3B C8B 120.0 . . ?
C4B C3B C2B 119.5(9) . . ?
C8B C3B C2B 120.5(9) . . ?
C5B C4B C3B 120.0 . . ?
C5B C4B H4B 120.0 . . ?
C3B C4B H4B 120.0 . . ?
C6B C5B C4B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
C5B C6B C7B 120.0 . . ?
C5B C6B Cl1B 120.5(6) . . ?
C7B C6B Cl1B 119.5(6) . . ?
C8B C7B C6B 120.0 . . ?
C8B C7B H7B 120.0 . . ?
C6B C7B H7B 120.0 . . ?
C7B C8B C3B 120.0 . . ?
C7B C8B H8B 120.0 . . ?
C3B C8B H8B 120.0 . . ?
C2C O3C H3OC 120(8) . . ?
O1C C1C O2C 126.9(16) . . ?
O1C C1C C2C 115.4(14) . . ?
O2C C1C C2C 117.7(15) . . ?
O3C C2C C1C 111.2(13) . . ?
O3C C2C C3C 111.2(12) . . ?
C1C C2C C3C 110.2(12) . . ?
O3C C2C H2C 108.1 . . ?
C1C C2C H2C 108.1 . . ?
C3C C2C H2C 108.1 . . ?
C4C C3C C8C 120.0 . . ?
C4C C3C C2C 119.3(8) . . ?
C8C C3C C2C 120.6(8) . . ?
C5C C4C C3C 120.0 . . ?
C5C C4C H4C 120.0 . . ?
C3C C4C H4C 120.0 . . ?
C6C C5C C4C 120.0 . . ?
C6C C5C H5C 120.0 . . ?
C4C C5C H5C 120.0 . . ?
C5C C6C C7C 120.0 . . ?
C5C C6C Cl1C 119.8(6) . . ?
C7C C6C Cl1C 120.2(6) . . ?
C8C C7C C6C 120.0 . . ?
C8C C7C H7C 120.0 . . ?
C6C C7C H7C 120.0 . . ?
C7C C8C C3C 120.0 . . ?
C7C C8C H8C 120.0 . . ?
C3C C8C H8C 120.0 . . ?
C2D O3D H3OD 90.8 . . ?
O1D C1D O2D 125.5(15) . . ?
O1D C1D C2D 118.7(14) . . ?
O2D C1D C2D 115.7(14) . . ?
O3D C2D C3D 106.9(11) . . ?
O3D C2D C1D 111.6(13) . . ?
C3D C2D C1D 108.9(12) . . ?
O3D C2D H2D 109.8 . . ?
C3D C2D H2D 109.8 . . ?
C1D C2D H2D 109.8 . . ?
C4D C3D C8D 120.0 . . ?
C4D C3D C2D 120.3(9) . . ?
C8D C3D C2D 119.7(9) . . ?
C5D C4D C3D 120.0 . . ?
C5D C4D H4D 120.0 . . ?
C3D C4D H4D 120.0 . . ?
C6D C5D C4D 120.0 . . ?
C6D C5D H5D 120.0 . . ?
C4D C5D H5D 120.0 . . ?
C5D C6D C7D 120.0 . . ?
C5D C6D Cl1D 121.1(6) . . ?
C7D C6D Cl1D 118.9(6) . . ?
C6D C7D C8D 120.0 . . ?
C6D C7D H7D 120.0 . . ?
C8D C7D H7D 120.0 . . ?
C7D C8D C3D 120.0 . . ?
C7D C8D H8D 120.0 . . ?
C3D C8D H8D 120.0 . . ?
C9A N1A H1A1 109.5 . . ?
C9A N1A H1A2 109.5 . . ?
H1A1 N1A H1A2 109.5 . . ?
C9A N1A H1A3 109.5 . . ?
H1A1 N1A H1A3 109.5 . . ?
H1A2 N1A H1A3 109.5 . . ?
C10A C9A N1A 108.2(13) . . ?
C10A C9A C11A 116.6(14) . . ?
N1A C9A C11A 110.9(13) . . ?
C10A C9A H9A 106.9 . . ?
N1A C9A H9A 106.9 . . ?
C11A C9A H9A 106.9 . . ?
C9A C10A H10A 109.5 . . ?
C9A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
C9A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C12A C11A C9A 113.9(14) . . ?
C12A C11A C16A 111.8(13) . . ?
C9A C11A C16A 110.8(13) . . ?
C12A C11A H11A 106.6 . . ?
C9A C11A H11A 106.6 . . ?
C16A C11A H11A 106.6 . . ?
C11A C12A C13A 112.6(13) . . ?
C11A C12A H12A 109.1 . . ?
C13A C12A H12A 109.1 . . ?
C11A C12A H12B 109.1 . . ?
C13A C12A H12B 109.1 . . ?
H12A C12A H12B 107.8 . . ?
C14A C13A C12A 111.8(13) . . ?
C14A C13A H13A 109.2 . . ?
C12A C13A H13A 109.2 . . ?
C14A C13A H13B 109.2 . . ?
C12A C13A H13B 109.2 . . ?
H13A C13A H13B 107.9 . . ?
C13A C14A C15A 110.6(13) . . ?
C13A C14A H14A 109.5 . . ?
C15A C14A H14A 109.5 . . ?
C13A C14A H14B 109.5 . . ?
C15A C14A H14B 109.5 . . ?
H14A C14A H14B 108.1 . . ?
C16A C15A C14A 112.6(13) . . ?
C16A C15A H15A 109.1 . . ?
C14A C15A H15A 109.1 . . ?
C16A C15A H15B 109.1 . . ?
C14A C15A H15B 109.1 . . ?
H15A C15A H15B 107.8 . . ?
C11A C16A C15A 112.2(13) . . ?
C11A C16A H16A 109.2 . . ?
C15A C16A H16A 109.2 . . ?
C11A C16A H16B 109.2 . . ?
C15A C16A H16B 109.2 . . ?
H16A C16A H16B 107.9 . . ?
C9B N1B H1B1 109.5 . . ?
C9B N1B H1B2 109.5 . . ?
H1B1 N1B H1B2 109.5 . . ?
C9B N1B H1B3 109.5 . . ?
H1B1 N1B H1B3 109.5 . . ?
H1B2 N1B H1B3 109.5 . . ?
N1B C9B C11B 111.8(13) . . ?
N1B C9B C10B 106.5(12) . . ?
C11B C9B C10B 114.7(13) . . ?
N1B C9B H9B 107.9 . . ?
C11B C9B H9B 107.9 . . ?
C10B C9B H9B 107.9 . . ?
C9B C10B H10D 109.5 . . ?
C9B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C9B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C9B C11B C12B 116.0(14) . . ?
C9B C11B C16B 110.4(14) . . ?
C12B C11B C16B 110.0(14) . . ?
C9B C11B H11B 106.6 . . ?
C12B C11B H11B 106.6 . . ?
C16B C11B H11B 106.6 . . ?
C11B C12B C13B 111.8(14) . . ?
C11B C12B H12C 109.3 . . ?
C13B C12B H12C 109.3 . . ?
C11B C12B H12D 109.3 . . ?
C13B C12B H12D 109.3 . . ?
H12C C12B H12D 107.9 . . ?
C14B C13B C12B 111.5(14) . . ?
C14B C13B H13C 109.3 . . ?
C12B C13B H13C 109.3 . . ?
C14B C13B H13D 109.3 . . ?
C12B C13B H13D 109.3 . . ?
H13C C13B H13D 108.0 . . ?
C13B C14B C15B 109.6(14) . . ?
C13B C14B H14C 109.7 . . ?
C15B C14B H14C 109.7 . . ?
C13B C14B H14D 109.7 . . ?
C15B C14B H14D 109.7 . . ?
H14C C14B H14D 108.2 . . ?
C14B C15B C16B 109.9(15) . . ?
C14B C15B H15C 109.7 . . ?
C16B C15B H15C 109.7 . . ?
C14B C15B H15D 109.7 . . ?
C16B C15B H15D 109.7 . . ?
H15C C15B H15D 108.2 . . ?
C11B C16B C15B 113.0(14) . . ?
C11B C16B H16C 109.0 . . ?
C15B C16B H16C 109.0 . . ?
C11B C16B H16D 109.0 . . ?
C15B C16B H16D 109.0 . . ?
H16C C16B H16D 107.8 . . ?
C9C N1C H1C1 109.5 . . ?
C9C N1C H1C2 109.5 . . ?
H1C1 N1C H1C2 109.5 . . ?
C9C N1C H1C3 109.5 . . ?
H1C1 N1C H1C3 109.5 . . ?
H1C2 N1C H1C3 109.5 . . ?
N1C C9C C10C 108.8(12) . . ?
N1C C9C C11C 109.5(12) . . ?
C10C C9C C11C 115.8(13) . . ?
N1C C9C H9C 107.5 . . ?
C10C C9C H9C 107.5 . . ?
C11C C9C H9C 107.5 . . ?
C9C C10C H10G 109.5 . . ?
C9C C10C H10H 109.5 . . ?
H10G C10C H10H 109.5 . . ?
C9C C10C H10I 109.5 . . ?
H10G C10C H10I 109.5 . . ?
H10H C10C H10I 109.5 . . ?
C16C C11C C12C 110.0(13) . . ?
C16C C11C C9C 111.3(13) . . ?
C12C C11C C9C 109.5(13) . . ?
C16C C11C H11C 108.7 . . ?
C12C C11C H11C 108.7 . . ?
C9C C11C H11C 108.7 . . ?
C13C C12C C11C 110.4(14) . . ?
C13C C12C H12E 109.6 . . ?
C11C C12C H12E 109.6 . . ?
C13C C12C H12F 109.6 . . ?
C11C C12C H12F 109.6 . . ?
H12E C12C H12F 108.1 . . ?
C14C C13C C12C 113.2(14) . . ?
C14C C13C H13E 108.9 . . ?
C12C C13C H13E 108.9 . . ?
C14C C13C H13F 108.9 . . ?
C12C C13C H13F 108.9 . . ?
H13E C13C H13F 107.8 . . ?
C13C C14C C15C 111.9(13) . . ?
C13C C14C H14E 109.2 . . ?
C15C C14C H14E 109.2 . . ?
C13C C14C H14F 109.2 . . ?
C15C C14C H14F 109.2 . . ?
H14E C14C H14F 107.9 . . ?
C16C C15C C14C 110.2(14) . . ?
C16C C15C H15E 109.6 . . ?
C14C C15C H15E 109.6 . . ?
C16C C15C H15F 109.6 . . ?
C14C C15C H15F 109.6 . . ?
H15E C15C H15F 108.1 . . ?
C15C C16C C11C 113.3(14) . . ?
C15C C16C H16E 108.9 . . ?
C11C C16C H16E 108.9 . . ?
C15C C16C H16F 108.9 . . ?
C11C C16C H16F 108.9 . . ?
H16E C16C H16F 107.7 . . ?
C9D N1D H1D1 109.5 . . ?
C9D N1D H1D2 109.5 . . ?
H1D1 N1D H1D2 109.5 . . ?
C9D N1D H1D3 109.5 . . ?
H1D1 N1D H1D3 109.5 . . ?
H1D2 N1D H1D3 109.5 . . ?
N1D C9D C10D 106.7(12) . . ?
N1D C9D C11D 109.2(13) . . ?
C10D C9D C11D 114.1(14) . . ?
N1D C9D H9D 108.9 . . ?
C10D C9D H9D 108.9 . . ?
C11D C9D H9D 108.9 . . ?
C9D C10D H10J 109.5 . . ?
C9D C10D H10K 109.5 . . ?
H10J C10D H10K 109.5 . . ?
C9D C10D H10L 109.5 . . ?
H10J C10D H10L 109.5 . . ?
H10K C10D H10L 109.5 . . ?
C12D C11D C9D 113.5(14) . . ?
C12D C11D C16D 109.9(13) . . ?
C9D C11D C16D 111.3(14) . . ?
C12D C11D H11D 107.3 . . ?
C9D C11D H11D 107.3 . . ?
C16D C11D H11D 107.3 . . ?
C13D C12D C11D 115.3(14) . . ?
C13D C12D H12G 108.5 . . ?
C11D C12D H12G 108.5 . . ?
C13D C12D H12H 108.5 . . ?
C11D C12D H12H 108.5 . . ?
H12G C12D H12H 107.5 . . ?
C12D C13D C14D 111.3(15) . . ?
C12D C13D H13G 109.4 . . ?
C14D C13D H13G 109.4 . . ?
C12D C13D H13H 109.4 . . ?
C14D C13D H13H 109.4 . . ?
H13G C13D H13H 108.0 . . ?
C13D C14D C15D 113.1(14) . . ?
C13D C14D H14G 109.0 . . ?
C15D C14D H14G 109.0 . . ?
C13D C14D H14H 109.0 . . ?
C15D C14D H14H 109.0 . . ?
H14G C14D H14H 107.8 . . ?
C14D C15D C16D 111.1(14) . . ?
C14D C15D H15G 109.4 . . ?
C16D C15D H15G 109.4 . . ?
C14D C15D H15H 109.4 . . ?
C16D C15D H15H 109.4 . . ?
H15G C15D H15H 108.0 . . ?
C15D C16D C11D 111.9(14) . . ?
C15D C16D H16G 109.2 . . ?
C11D C16D H16G 109.2 . . ?
C15D C16D H16H 109.2 . . ?
C11D C16D H16H 109.2 . . ?
H16G C16D H16H 107.9 . . ?

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
O1A C1A C2A O3A -153.9(14) . . . . ?
O2A C1A C2A O3A 28.8(19) . . . . ?
O1A C1A C2A C3A 83.2(16) . . . . ?
O2A C1A C2A C3A -94.2(16) . . . . ?
O3A C2A C3A C4A 172.3(9) . . . . ?
C1A C2A C3A C4A -67.9(13) . . . . ?
O3A C2A C3A C8A -13.8(16) . . . . ?
C1A C2A C3A C8A 105.9(12) . . . . ?
C8A C3A C4A C5A 0.0 . . . . ?
C2A C3A C4A C5A 173.9(11) . . . . ?
C3A C4A C5A C6A 0.0 . . . . ?
C4A C5A C6A C7A 0.0 . . . . ?
C4A C5A C6A Cl1A -176.6(9) . . . . ?
C5A C6A C7A C8A 0.0 . . . . ?
Cl1A C6A C7A C8A 176.6(9) . . . . ?
C6A C7A C8A C3A 0.0 . . . . ?
C4A C3A C8A C7A 0.0 . . . . ?
C2A C3A C8A C7A -173.8(12) . . . . ?
O2B C1B C2B O3B 15(2) . . . . ?
O1B C1B C2B O3B -163.1(13) . . . . ?
O2B C1B C2B C3B -103.9(16) . . . . ?
O1B C1B C2B C3B 77.5(17) . . . . ?
O3B C2B C3B C4B 171.8(9) . . . . ?
C1B C2B C3B C4B -65.1(15) . . . . ?
O3B C2B C3B C8B -7.0(15) . . . . ?
C1B C2B C3B C8B 116.2(12) . . . . ?
C8B C3B C4B C5B 0.0 . . . . ?
C2B C3B C4B C5B -178.8(12) . . . . ?
C3B C4B C5B C6B 0.0 . . . . ?
C4B C5B C6B C7B 0.0 . . . . ?
C4B C5B C6B Cl1B -179.1(9) . . . . ?
C5B C6B C7B C8B 0.0 . . . . ?
Cl1B C6B C7B C8B 179.1(9) . . . . ?
C6B C7B C8B C3B 0.0 . . . . ?
C4B C3B C8B C7B 0.0 . . . . ?
C2B C3B C8B C7B 178.8(12) . . . . ?
O1C C1C C2C O3C -167.5(13) . . . . ?
O2C C1C C2C O3C 14.1(19) . . . . ?
O1C C1C C2C C3C 68.8(17) . . . . ?
O2C C1C C2C C3C -109.6(15) . . . . ?
O3C C2C C3C C4C -38.9(15) . . . . ?
C1C C2C C3C C4C 84.8(13) . . . . ?
O3C C2C C3C C8C 143.0(10) . . . . ?
C1C C2C C3C C8C -93.2(13) . . . . ?
C8C C3C C4C C5C 0.0 . . . . ?
C2C C3C C4C C5C -178.1(11) . . . . ?
C3C C4C C5C C6C 0.0 . . . . ?
C4C C5C C6C C7C 0.0 . . . . ?
C4C C5C C6C Cl1C 179.5(8) . . . . ?
C5C C6C C7C C8C 0.0 . . . . ?
Cl1C C6C C7C C8C -179.5(8) . . . . ?
C6C C7C C8C C3C 0.0 . . . . ?
C4C C3C C8C C7C 0.0 . . . . ?
C2C C3C C8C C7C 178.0(11) . . . . ?
O1D C1D C2D O3D 22.5(19) . . . . ?
O2D C1D C2D O3D -158.5(12) . . . . ?
O1D C1D C2D C3D -95.3(16) . . . . ?
O2D C1D C2D C3D 83.7(15) . . . . ?
O3D C2D C3D C4D -59.5(13) . . . . ?
C1D C2D C3D C4D 61.2(14) . . . . ?
O3D C2D C3D C8D 121.8(10) . . . . ?
C1D C2D C3D C8D -117.5(11) . . . . ?
C8D C3D C4D C5D 0.0 . . . . ?
C2D C3D C4D C5D -178.7(10) . . . . ?
C3D C4D C5D C6D 0.0 . . . . ?
C4D C5D C6D C7D 0.0 . . . . ?
C4D C5D C6D Cl1D 179.9(8) . . . . ?
C5D C6D C7D C8D 0.0 . . . . ?
Cl1D C6D C7D C8D -179.9(8) . . . . ?
C6D C7D C8D C3D 0.0 . . . . ?
C4D C3D C8D C7D 0.0 . . . . ?
C2D C3D C8D C7D 178.7(10) . . . . ?
C10A C9A C11A C12A 54.8(19) . . . . ?
N1A C9A C11A C12A -69.7(18) . . . . ?
C10A C9A C11A C16A -72.3(19) . . . . ?
N1A C9A C11A C16A 163.2(13) . . . . ?
C9A C11A C12A C13A -179.5(13) . . . . ?
C16A C11A C12A C13A -53.0(18) . . . . ?
C11A C12A C13A C14A 54.6(19) . . . . ?
C12A C13A C14A C15A -54.0(18) . . . . ?
C13A C14A C15A C16A 53.8(18) . . . . ?
C12A C11A C16A C15A 52.2(19) . . . . ?
C9A C11A C16A C15A -179.6(14) . . . . ?
C14A C15A C16A C11A -53.0(19) . . . . ?
N1B C9B C11B C12B -65.8(18) . . . . ?
C10B C9B C11B C12B 55.6(19) . . . . ?
N1B C9B C11B C16B 168.2(13) . . . . ?
C10B C9B C11B C16B -70.4(18) . . . . ?
C9B C11B C12B C13B -179.2(14) . . . . ?
C16B C11B C12B C13B -53.1(19) . . . . ?
C11B C12B C13B C14B 56.9(19) . . . . ?
C12B C13B C14B C15B -58.6(19) . . . . ?
C13B C14B C15B C16B 57.6(19) . . . . ?
C9B C11B C16B C15B -176.9(14) . . . . ?
C12B C11B C16B C15B 54(2) . . . . ?
C14B C15B C16B C11B -57(2) . . . . ?
N1C C9C C11C C16C 69.5(16) . . . . ?
C10C C9C C11C C16C -167.0(13) . . . . ?
N1C C9C C11C C12C -168.7(13) . . . . ?
C10C C9C C11C C12C -45.3(19) . . . . ?
C16C C11C C12C C13C -53.3(18) . . . . ?
C9C C11C C12C C13C -175.8(13) . . . . ?
C11C C12C C13C C14C 54.7(19) . . . . ?
C12C C13C C14C C15C -55.1(19) . . . . ?
C13C C14C C15C C16C 54.1(19) . . . . ?
C14C C15C C16C C11C -55.3(19) . . . . ?
C12C C11C C16C C15C 55.6(19) . . . . ?
C9C C11C C16C C15C 177.1(14) . . . . ?
N1D C9D C11D C12D -176.6(14) . . . . ?
C10D C9D C11D C12D -57.3(19) . . . . ?
N1D C9D C11D C16D 58.9(17) . . . . ?
C10D C9D C11D C16D 178.1(13) . . . . ?
C9D C11D C12D C13D -178.1(15) . . . . ?
C16D C11D C12D C13D -53(2) . . . . ?
C11D C12D C13D C14D 53(2) . . . . ?
C12D C13D C14D C15D -53(2) . . . . ?
C13D C14D C15D C16D 54(2) . . . . ?
C14D C15D C16D C11D -53.3(18) . . . . ?
C12D C11D C16D C15D 51.8(18) . . . . ?
C9D C11D C16D C15D 178.4(14) . . . . ?

_refine_diff_density_max         0.496
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.108



####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2059733'
loop_
_audit_author_name
_audit_author_address
'Laura Bereczki'
;Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2021-01-29 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
(R)-(1-cyclohexylethyl)ammonium (R)-2-(2-chlorophenyl)-2-hydroxyacetate
;
_chemical_name_common            
;
(R)-(1-cyclohexylethyl)ammonium (R)-2-chloromandelate'
;
_chemical_melting_point          429(1)
_chemical_formula_moiety         'C8 H18 N 1+, C8 H6 Cl O3 1-'
_chemical_formula_sum            'C16 H24 Cl N O3'
_chemical_formula_weight         313.81

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.7938(3)
_cell_length_b                   8.6704(3)
_cell_length_c                   27.7144(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1632.52(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    4687
_cell_measurement_theta_min      6.71
_cell_measurement_theta_max      66.27
_exptl_crystal_description       chunk
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    2.151
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.5750
_exptl_absorpt_correction_T_max  0.8212
_exptl_absorpt_process_details   
;
  NUMABS, Numerical Absorption correction Program (T.Higashi, 2011)
;
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  RAXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            7677
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         6.710
_diffrn_reflns_theta_max         66.564
_diffrn_reflns_theta_full        66.564
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measured_fraction_theta_full 0.880
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_Laue_measured_fraction_full 0.880
_diffrn_reflns_point_group_measured_fraction_max 0.814
_diffrn_reflns_point_group_measured_fraction_full 0.814
_reflns_number_total             7677
_reflns_number_gt                5310
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.568
_reflns_Friedel_fraction_max     0.719
_reflns_Friedel_fraction_full    0.719

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_cell_refinement       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_data_reduction        
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_structure_solution    
;
Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.
;
_computing_publication_material  
;
C. F. Macrae, J. Appl. Cryst., 41, 466-470, 2008
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0557P)²+11.8532P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 289 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(4)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         7677
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1422
_refine_ls_R_factor_gt           0.0931
_refine_ls_wR_factor_ref         0.2515
_refine_ls_wR_factor_gt          0.1968
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_restrained_S_all      1.130
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.5863(6) 0.7133(6) 0.77015(13) 0.0715(16) Uani 1 1 d . . . . .
O1 O 0.0859(16) 0.4207(13) 0.9876(3) 0.051(3) Uani 1 1 d . . . . .
O2 O 0.3727(15) 0.5444(13) 1.0015(3) 0.050(3) Uani 1 1 d . . . . .
O3 O -0.0753(14) 0.6786(13) 0.9495(3) 0.050(3) Uani 1 1 d . . . . .
H3 H -0.1215 0.7614 0.9582 0.075 Uiso 1 1 calc R U . . .
C1 C 0.202(3) 0.534(2) 0.9851(5) 0.046(5) Uani 1 1 d . . . . .
C2 C 0.136(2) 0.679(2) 0.9571(5) 0.045(5) Uani 1 1 d . . . . .
H2 H 0.1683 0.7694 0.9768 0.054 Uiso 1 1 calc R U . . .
C3 C 0.244(2) 0.695(2) 0.9097(5) 0.043(5) Uani 1 1 d . . . . .
C4 C 0.161(2) 0.6335(19) 0.8673(5) 0.042(5) Uani 1 1 d . . . . .
H4 H 0.0373 0.5878 0.8682 0.051 Uiso 1 1 calc R U . . .
C5 C 0.264(2) 0.6417(19) 0.8240(5) 0.051(5) Uani 1 1 d . . . . .
H5 H 0.2085 0.6056 0.7955 0.061 Uiso 1 1 calc R U . . .
C6 C 0.452(3) 0.705(2) 0.8244(5) 0.057(5) Uani 1 1 d . . . . .
C7 C 0.537(2) 0.763(2) 0.8656(5) 0.054(5) Uani 1 1 d . . . . .
H7 H 0.6614 0.8074 0.8649 0.065 Uiso 1 1 calc R U . . .
C8 C 0.431(2) 0.7534(19) 0.9086(5) 0.051(5) Uani 1 1 d . . . . .
H8 H 0.4885 0.7877 0.9371 0.062 Uiso 1 1 calc R U . . .
N1 N 0.6882(16) 0.3622(16) 0.9637(3) 0.051(4) Uani 1 1 d . . . . .
H1A H 0.8119 0.3919 0.9687 0.077 Uiso 1 1 calc R U . . .
H1B H 0.6708 0.2678 0.9756 0.077 Uiso 1 1 calc R U . . .
H1C H 0.6066 0.4274 0.9784 0.077 Uiso 1 1 calc R U . . .
C9 C 0.646(2) 0.361(2) 0.9101(5) 0.054(5) Uani 1 1 d . . . . .
H9 H 0.6344 0.4688 0.8995 0.065 Uiso 1 1 calc R U . . .
C10 C 0.446(2) 0.2839(19) 0.9025(5) 0.052(5) Uani 1 1 d . . . . .
H10A H 0.4466 0.1844 0.9178 0.079 Uiso 1 1 calc R U . . .
H10B H 0.4223 0.2719 0.8686 0.079 Uiso 1 1 calc R U . . .
H10C H 0.3449 0.3467 0.9165 0.079 Uiso 1 1 calc R U . . .
C11 C 0.816(2) 0.287(2) 0.8815(4) 0.050(5) Uani 1 1 d . . . . .
H11 H 0.9390 0.3292 0.8941 0.060 Uiso 1 1 calc R U . . .
C12 C 0.825(2) 0.114(2) 0.8874(5) 0.054(6) Uani 1 1 d . . . . .
H12A H 0.7029 0.0690 0.8763 0.065 Uiso 1 1 calc R U . . .
H12B H 0.8407 0.0894 0.9213 0.065 Uiso 1 1 calc R U . . .
C13 C 0.999(2) 0.046(2) 0.8586(5) 0.065(6) Uani 1 1 d . . . . .
H13A H 1.1220 0.0824 0.8719 0.078 Uiso 1 1 calc R U . . .
H13B H 0.9966 -0.0659 0.8612 0.078 Uiso 1 1 calc R U . . .
C14 C 0.984(2) 0.092(2) 0.8059(5) 0.065(6) Uani 1 1 d . . . . .
H14A H 0.8667 0.0463 0.7919 0.078 Uiso 1 1 calc R U . . .
H14B H 1.0971 0.0520 0.7886 0.078 Uiso 1 1 calc R U . . .
C15 C 0.975(2) 0.267(2) 0.7997(5) 0.063(6) Uani 1 1 d . . . . .
H15A H 0.9611 0.2918 0.7658 0.075 Uiso 1 1 calc R U . . .
H15B H 1.0973 0.3123 0.8111 0.075 Uiso 1 1 calc R U . . .
C16 C 0.800(2) 0.335(2) 0.8283(5) 0.055(5) Uani 1 1 d . . . . .
H16A H 0.8018 0.4469 0.8260 0.066 Uiso 1 1 calc R U . . .
H16B H 0.6771 0.2984 0.8149 0.066 Uiso 1 1 calc R U . . .


_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
Cl1 C6 1.761(15) . ?
O1 C1 1.258(19) . ?
O2 C1 1.251(17) . ?
O3 C2 1.450(15) . ?
O3 H3 0.8200 . ?
C1 C2 1.55(2) . ?
C2 C3 1.511(17) . ?
C2 H2 0.9800 . ?
C3 C8 1.367(19) . ?
C3 C4 1.408(17) . ?
C4 C5 1.390(17) . ?
C4 H4 0.9300 . ?
C5 C6 1.39(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(19) . ?
C7 C8 1.392(18) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
N1 C9 1.514(14) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C9 C10 1.528(19) . ?
C9 C11 1.54(2) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.50(2) . ?
C11 C16 1.536(16) . ?
C11 H11 0.9800 . ?
C12 C13 1.543(19) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.517(18) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.53(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.55(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 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
C2 O3 H3 109.5 . . ?
O2 C1 O1 128.2(18) . . ?
O2 C1 C2 112.9(17) . . ?
O1 C1 C2 118.8(15) . . ?
O3 C2 C3 111.0(11) . . ?
O3 C2 C1 110.8(13) . . ?
C3 C2 C1 111.6(13) . . ?
O3 C2 H2 107.8 . . ?
C3 C2 H2 107.8 . . ?
C1 C2 H2 107.8 . . ?
C8 C3 C4 119.6(13) . . ?
C8 C3 C2 120.4(13) . . ?
C4 C3 C2 119.7(14) . . ?
C5 C4 C3 119.9(14) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 118.4(14) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C7 C6 C5 122.4(14) . . ?
C7 C6 Cl1 118.5(14) . . ?
C5 C6 Cl1 119.1(12) . . ?
C6 C7 C8 118.1(15) . . ?
C6 C7 H7 121.0 . . ?
C8 C7 H7 121.0 . . ?
C3 C8 C7 121.4(14) . . ?
C3 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C9 N1 H1A 109.5 . . ?
C9 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C9 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
N1 C9 C10 107.7(12) . . ?
N1 C9 C11 111.5(12) . . ?
C10 C9 C11 114.1(13) . . ?
N1 C9 H9 107.8 . . ?
C10 C9 H9 107.8 . . ?
C11 C9 H9 107.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 112.3(14) . . ?
C12 C11 C9 113.2(14) . . ?
C16 C11 C9 109.0(13) . . ?
C12 C11 H11 107.3 . . ?
C16 C11 H11 107.3 . . ?
C9 C11 H11 107.3 . . ?
C11 C12 C13 111.1(15) . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 110.2(14) . . ?
C14 C13 H13A 109.6 . . ?
C12 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C15 111.9(15) . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C16 110.7(15) . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C11 C16 C15 109.4(13) . . ?
C11 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
C11 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 O3 -165.5(12) . . . . ?
O1 C1 C2 O3 16.7(18) . . . . ?
O2 C1 C2 C3 70.4(16) . . . . ?
O1 C1 C2 C3 -107.5(16) . . . . ?
O3 C2 C3 C8 155.8(15) . . . . ?
C1 C2 C3 C8 -80(2) . . . . ?
O3 C2 C3 C4 -31(2) . . . . ?
C1 C2 C3 C4 93.3(17) . . . . ?
C8 C3 C4 C5 -4(3) . . . . ?
C2 C3 C4 C5 -177.3(15) . . . . ?
C3 C4 C5 C6 3(2) . . . . ?
C4 C5 C6 C7 -2(3) . . . . ?
C4 C5 C6 Cl1 178.9(12) . . . . ?
C5 C6 C7 C8 2(3) . . . . ?
Cl1 C6 C7 C8 -178.8(12) . . . . ?
C4 C3 C8 C7 4(3) . . . . ?
C2 C3 C8 C7 177.4(15) . . . . ?
C6 C7 C8 C3 -3(3) . . . . ?
N1 C9 C11 C12 72.7(18) . . . . ?
C10 C9 C11 C12 -49.6(18) . . . . ?
N1 C9 C11 C16 -161.5(14) . . . . ?
C10 C9 C11 C16 76.2(18) . . . . ?
C16 C11 C12 C13 56.6(18) . . . . ?
C9 C11 C12 C13 -179.4(11) . . . . ?
C11 C12 C13 C14 -55.5(19) . . . . ?
C12 C13 C14 C15 56(2) . . . . ?
C13 C14 C15 C16 -57.0(19) . . . . ?
C12 C11 C16 C15 -56.3(19) . . . . ?
C9 C11 C16 C15 177.5(14) . . . . ?
C14 C15 C16 C11 55.5(18) . . . . ?

_refine_diff_density_max         0.834
_refine_diff_density_min         -0.709
_refine_diff_density_rms         0.099



####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2059735'
loop_
_audit_author_name
_audit_author_address
'Laura Bereczki'
;Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2021-01-29 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
(S)-(1-cyclohexylethyl)ammonium (R,S)-2-(2-chlorophenyl)-2-hydroxyacetate
;
_chemical_name_common            
;
(S)-(1-cyclohexylethyl)ammonium (R,S)-2-chloromandelate
;
_chemical_melting_point          411(1)
_chemical_formula_moiety         'C8 H18 N 1+, C8 H6 Cl O3 1-'
_chemical_formula_sum            'C16 H24 Cl N O3'
_chemical_formula_weight         313.81

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   24.2266(8)
_cell_length_b                   10.0661(8)
_cell_length_c                   13.3665(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.5330(10)
_cell_angle_gamma                90
_cell_volume                     3256.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    119(2)
_cell_measurement_reflns_used    18379
_cell_measurement_theta_min      3.310
_cell_measurement_theta_max      71.835

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   0.881501
_exptl_transmission_factor_max   0.964339
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.44
_exptl_absorpt_coefficient_mu    2.157
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_process_details   
;
  NUMABS, Numerical Absorption correction Program (T.Higashi, 2011)
;
_diffrn_ambient_temperature      119(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_detector       RX
_diffrn_measurement_device       RAXIS-RAPID
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_method       dtprofit.ref
_diffrn_reflns_number            18879
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.310
_diffrn_reflns_theta_max         68.245
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.952
_reflns_number_total             5644
_reflns_number_gt                5111
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_max     0.927
_reflns_Friedel_fraction_full    0.931

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_cell_refinement       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_data_reduction        
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_structure_solution    
;
  Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.
;
_computing_publication_material  
;
C. F. Macrae, J. Appl. Cryst., 41, 466-470, 2008
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+1.2400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1843 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.099(9)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5644
_refine_ls_number_parameters     413
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1100
_refine_ls_wR_factor_gt          0.1070
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1' Cl 0.47469(5) 0.70134(14) 0.37371(11) 0.0589(4) Uani 1 1 d . . . . .
Cl1 Cl 0.04127(6) -0.01547(14) 0.10348(11) 0.0662(4) Uani 1 1 d . . . . .
O1' O 0.23647(12) 0.4738(3) -0.0106(2) 0.0354(7) Uani 1 1 d . . . . .
O3' O 0.28364(14) 0.7093(3) -0.0062(2) 0.0424(8) Uani 1 1 d . . . . .
O2' O 0.26920(11) 0.4264(3) 0.1439(2) 0.0316(7) Uani 1 1 d . . . . .
O2 O 0.26713(11) 0.1285(3) 0.3574(2) 0.0309(7) Uani 1 1 d . . . . .
O1 O 0.26513(13) 0.0807(3) 0.5196(2) 0.0353(7) Uani 1 1 d . . . . .
O3 O 0.21848(15) -0.1534(3) 0.4866(3) 0.0403(9) Uani 1 1 d . . . . .
N1' N 0.30387(15) 0.1570(4) 0.1597(3) 0.0307(8) Uani 1 1 d . . . . .
N1 N 0.22509(15) 0.3882(4) 0.3301(3) 0.0299(8) Uani 1 1 d . . . . .
C8' C 0.32081(17) 0.6612(4) 0.2617(3) 0.0333(10) Uani 1 1 d . . . . .
H8' H 0.285833 0.650959 0.286701 0.040 Uiso 1 1 calc R U . . .
C7' C 0.36570(18) 0.6708(4) 0.3274(4) 0.0388(11) Uani 1 1 d . . . . .
H7' H 0.361202 0.666668 0.396089 0.047 Uiso 1 1 calc R U . . .
C3' C 0.32631(17) 0.6664(4) 0.1581(3) 0.0294(9) Uani 1 1 d . . . . .
C6 C 0.09694(18) -0.0347(4) 0.1890(4) 0.0395(11) Uani 1 1 d . . . . .
C3 C 0.18551(17) -0.0705(4) 0.3248(3) 0.0295(10) Uani 1 1 d . . . . .
C16' C 0.38725(18) 0.3007(4) 0.2908(3) 0.0330(10) Uani 1 1 d . . . . .
H16A H 0.390348 0.374053 0.244361 0.040 Uiso 1 1 calc R U . . .
H16B H 0.349491 0.298115 0.312055 0.040 Uiso 1 1 calc R U . . .
C5' C 0.42459(18) 0.6931(5) 0.1887(4) 0.0435(12) Uani 1 1 d . . . . .
H5' H 0.459539 0.704781 0.163903 0.052 Uiso 1 1 calc R U . . .
C6' C 0.41781(18) 0.6869(4) 0.2906(4) 0.0386(11) Uani 1 1 d . . . . .
C2' C 0.27629(17) 0.6511(4) 0.0883(3) 0.0318(10) Uani 1 1 d . . . . .
H2' H 0.245371 0.696389 0.118652 0.038 Uiso 1 1 calc R U . . .
C7 C 0.14957(19) -0.0454(4) 0.1552(4) 0.0378(11) Uani 1 1 d . . . . .
H7 H 0.155520 -0.039567 0.087038 0.045 Uiso 1 1 calc R U . . .
C4 C 0.13212(18) -0.0580(4) 0.3569(4) 0.0376(11) Uani 1 1 d . . . . .
H4 H 0.126077 -0.062126 0.425072 0.045 Uiso 1 1 calc R U . . .
C2 C 0.23358(18) -0.0853(4) 0.3994(3) 0.0307(10) Uani 1 1 d . . . . .
H2 H 0.262612 -0.136237 0.367965 0.037 Uiso 1 1 calc R U . . .
C1 C 0.25717(16) 0.0526(4) 0.4292(3) 0.0276(9) Uani 1 1 d . . . . .
C12' C 0.40016(17) 0.0539(4) 0.3109(3) 0.0347(11) Uani 1 1 d . . . . .
H12A H 0.362759 0.039318 0.331531 0.042 Uiso 1 1 calc R U . . .
H12B H 0.412038 -0.025787 0.277177 0.042 Uiso 1 1 calc R U . . .
C4' C 0.37886(18) 0.6819(4) 0.1241(4) 0.0385(11) Uani 1 1 d . . . . .
H4' H 0.383597 0.684811 0.055485 0.046 Uiso 1 1 calc R U . . .
C11 C 0.13518(17) 0.4167(4) 0.2344(3) 0.0320(10) Uani 1 1 d . . . . .
H11 H 0.160626 0.458617 0.188955 0.038 Uiso 1 1 calc R U . . .
C8 C 0.19339(18) -0.0648(4) 0.2227(3) 0.0321(10) Uani 1 1 d . . . . .
H8 H 0.228807 -0.074257 0.199486 0.038 Uiso 1 1 calc R U . . .
C11' C 0.40034(16) 0.1705(4) 0.2376(3) 0.0308(10) Uani 1 1 d . . . . .
H11' H 0.438355 0.178622 0.216119 0.037 Uiso 1 1 calc R U . . .
C15' C 0.42616(19) 0.3239(5) 0.3815(4) 0.0394(11) Uani 1 1 d . . . . .
H15A H 0.463620 0.334001 0.359841 0.047 Uiso 1 1 calc R U . . .
H15B H 0.415912 0.405254 0.414833 0.047 Uiso 1 1 calc R U . . .
C12 C 0.09510(18) 0.3316(5) 0.1703(4) 0.0398(11) Uani 1 1 d . . . . .
H12C H 0.115609 0.263818 0.136168 0.048 Uiso 1 1 calc R U . . .
H12D H 0.069537 0.287469 0.213168 0.048 Uiso 1 1 calc R U . . .
C1' C 0.25964(16) 0.5042(4) 0.0716(3) 0.0282(9) Uani 1 1 d . . . . .
C5 C 0.08769(19) -0.0394(4) 0.2900(4) 0.0433(12) Uani 1 1 d . . . . .
H5 H 0.052138 -0.030353 0.312618 0.052 Uiso 1 1 calc R U . . .
C9' C 0.36462(17) 0.1432(4) 0.1435(3) 0.0330(10) Uani 1 1 d . . . . .
H9' H 0.371324 0.051128 0.123496 0.040 Uiso 1 1 calc R U . . .
C14' C 0.42376(17) 0.2084(5) 0.4542(3) 0.0399(11) Uani 1 1 d . . . . .
H14A H 0.386955 0.202563 0.479664 0.048 Uiso 1 1 calc R U . . .
H14B H 0.449601 0.223874 0.510551 0.048 Uiso 1 1 calc R U . . .
C13' C 0.43798(18) 0.0780(5) 0.4034(3) 0.0394(11) Uani 1 1 d . . . . .
H13A H 0.434200 0.005333 0.450254 0.047 Uiso 1 1 calc R U . . .
H13B H 0.476087 0.080558 0.384104 0.047 Uiso 1 1 calc R U . . .
C9 C 0.16985(16) 0.3274(4) 0.3056(3) 0.0302(10) Uani 1 1 d . . . . .
H9 H 0.176274 0.243902 0.270157 0.036 Uiso 1 1 calc R U . . .
C10 C 0.14344(18) 0.2923(4) 0.4032(3) 0.0392(11) Uani 1 1 d . . . . .
H10A H 0.165420 0.226263 0.438201 0.059 Uiso 1 1 calc R U . . .
H10B H 0.106946 0.258029 0.389101 0.059 Uiso 1 1 calc R U . . .
H10C H 0.141287 0.370417 0.444058 0.059 Uiso 1 1 calc R U . . .
C16 C 0.10425(19) 0.5282(4) 0.2855(3) 0.0372(11) Uani 1 1 d . . . . .
H16C H 0.079423 0.490177 0.332779 0.045 Uiso 1 1 calc R U . . .
H16D H 0.130507 0.584330 0.322469 0.045 Uiso 1 1 calc R U . . .
C15 C 0.07114(19) 0.6121(5) 0.2089(4) 0.0432(12) Uani 1 1 d . . . . .
H15C H 0.049904 0.677879 0.243683 0.052 Uiso 1 1 calc R U . . .
H15D H 0.096373 0.658693 0.166830 0.052 Uiso 1 1 calc R U . . .
C13 C 0.0629(2) 0.4154(5) 0.0935(4) 0.0495(13) Uani 1 1 d . . . . .
H13C H 0.036670 0.359645 0.056161 0.059 Uiso 1 1 calc R U . . .
H13D H 0.088146 0.452780 0.046710 0.059 Uiso 1 1 calc R U . . .
C10' C 0.37774(19) 0.2320(5) 0.0555(3) 0.0455(12) Uani 1 1 d . . . . .
H10D H 0.373838 0.323423 0.074356 0.068 Uiso 1 1 calc R U . . .
H10E H 0.352675 0.212550 -0.000246 0.068 Uiso 1 1 calc R U . . .
H10F H 0.414967 0.216044 0.036783 0.068 Uiso 1 1 calc R U . . .
C14 C 0.03222(19) 0.5270(5) 0.1437(4) 0.0472(13) Uani 1 1 d . . . . .
H14C H 0.004010 0.489479 0.184531 0.057 Uiso 1 1 calc R U . . .
H14D H 0.014005 0.582284 0.092753 0.057 Uiso 1 1 calc R U . . .
H1N' H 0.2829(19) 0.096(5) 0.109(4) 0.045(13) Uiso 1 1 d . . . . .
H2N' H 0.2948(18) 0.130(5) 0.218(4) 0.041(14) Uiso 1 1 d . . . . .
H1N H 0.227(2) 0.464(6) 0.378(4) 0.066(16) Uiso 1 1 d . . . . .
H2N H 0.2422(16) 0.418(4) 0.276(3) 0.033(12) Uiso 1 1 d . . . . .
H3N' H 0.2924(17) 0.244(5) 0.147(3) 0.035(12) Uiso 1 1 d . . . . .
H3N H 0.2473(19) 0.328(5) 0.361(4) 0.046(14) Uiso 1 1 d . . . . .
H1O H 0.223(2) -0.225(6) 0.476(5) 0.07(2) Uiso 1 1 d . . . . .
H1O' H 0.274(3) 0.791(9) 0.005(6) 0.14(3) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1' C6' 1.738(5) . ?
Cl1 C6 1.739(5) . ?
O1' C1' 1.250(5) . ?
O3' C2' 1.411(5) . ?
O3' H1O' 0.87(9) . ?
O2' C1' 1.258(5) . ?
O2 C1 1.258(5) . ?
O1 C1 1.248(5) . ?
O3 C2 1.415(5) . ?
O3 H1O 0.74(6) . ?
N1' C9' 1.504(5) . ?
N1' H1N' 1.04(5) . ?
N1' H2N' 0.86(5) . ?
N1' H3N' 0.93(5) . ?
N1 C9 1.495(5) . ?
N1 H1N 1.00(6) . ?
N1 H2N 0.90(4) . ?
N1 H3N 0.90(5) . ?
C8' C7' 1.371(6) . ?
C8' C3' 1.399(6) . ?
C8' H8' 0.9300 . ?
C7' C6' 1.385(6) . ?
C7' H7' 0.9300 . ?
C3' C4' 1.379(6) . ?
C3' C2' 1.504(6) . ?
C6 C7 1.376(6) . ?
C6 C5 1.379(7) . ?
C3 C4 1.387(6) . ?
C3 C8 1.388(6) . ?
C3 C2 1.507(6) . ?
C16' C15' 1.520(6) . ?
C16' C11' 1.531(5) . ?
C16' H16A 0.9700 . ?
C16' H16B 0.9700 . ?
C5' C4' 1.378(6) . ?
C5' C6' 1.380(6) . ?
C5' H5' 0.9300 . ?
C2' C1' 1.546(5) . ?
C2' H2' 0.9800 . ?
C7 C8 1.376(6) . ?
C7 H7 0.9300 . ?
C4 C5 1.382(6) . ?
C4 H4 0.9300 . ?
C2 C1 1.547(5) . ?
C2 H2 0.9800 . ?
C12' C13' 1.526(6) . ?
C12' C11' 1.529(6) . ?
C12' H12A 0.9700 . ?
C12' H12B 0.9700 . ?
C4' H4' 0.9300 . ?
C11 C16 1.527(6) . ?
C11 C12 1.529(6) . ?
C11 C9 1.532(6) . ?
C11 H11 0.9800 . ?
C8 H8 0.9300 . ?
C11' C9' 1.520(6) . ?
C11' H11' 0.9800 . ?
C15' C14' 1.518(7) . ?
C15' H15A 0.9700 . ?
C15' H15B 0.9700 . ?
C12 C13 1.517(7) . ?
C12 H12C 0.9700 . ?
C12 H12D 0.9700 . ?
C5 H5 0.9300 . ?
C9' C10' 1.522(6) . ?
C9' H9' 0.9800 . ?
C14' C13' 1.524(6) . ?
C14' H14A 0.9700 . ?
C14' H14B 0.9700 . ?
C13' H13A 0.9700 . ?
C13' H13B 0.9700 . ?
C9 C10 1.521(6) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C16 C15 1.527(6) . ?
C16 H16C 0.9700 . ?
C16 H16D 0.9700 . ?
C15 C14 1.520(7) . ?
C15 H15C 0.9700 . ?
C15 H15D 0.9700 . ?
C13 C14 1.519(7) . ?
C13 H13C 0.9700 . ?
C13 H13D 0.9700 . ?
C10' H10D 0.9600 . ?
C10' H10E 0.9600 . ?
C10' H10F 0.9600 . ?
C14 H14C 0.9700 . ?
C14 H14D 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
C2' O3' H1O' 101(6) . . ?
C2 O3 H1O 105(5) . . ?
C9' N1' H1N' 108(2) . . ?
C9' N1' H2N' 113(3) . . ?
H1N' N1' H2N' 106(4) . . ?
C9' N1' H3N' 110(3) . . ?
H1N' N1' H3N' 108(4) . . ?
H2N' N1' H3N' 112(4) . . ?
C9 N1 H1N 119(3) . . ?
C9 N1 H2N 114(3) . . ?
H1N N1 H2N 104(4) . . ?
C9 N1 H3N 110(3) . . ?
H1N N1 H3N 102(4) . . ?
H2N N1 H3N 108(4) . . ?
C7' C8' C3' 121.6(4) . . ?
C7' C8' H8' 119.2 . . ?
C3' C8' H8' 119.2 . . ?
C8' C7' C6' 119.4(4) . . ?
C8' C7' H7' 120.3 . . ?
C6' C7' H7' 120.3 . . ?
C4' C3' C8' 117.4(4) . . ?
C4' C3' C2' 122.6(4) . . ?
C8' C3' C2' 120.0(4) . . ?
C7 C6 C5 120.8(4) . . ?
C7 C6 Cl1 119.7(4) . . ?
C5 C6 Cl1 119.5(4) . . ?
C4 C3 C8 118.2(4) . . ?
C4 C3 C2 120.5(4) . . ?
C8 C3 C2 121.3(4) . . ?
C15' C16' C11' 111.6(4) . . ?
C15' C16' H16A 109.3 . . ?
C11' C16' H16A 109.3 . . ?
C15' C16' H16B 109.3 . . ?
C11' C16' H16B 109.3 . . ?
H16A C16' H16B 108.0 . . ?
C4' C5' C6' 119.1(4) . . ?
C4' C5' H5' 120.4 . . ?
C6' C5' H5' 120.4 . . ?
C5' C6' C7' 120.4(4) . . ?
C5' C6' Cl1' 120.1(4) . . ?
C7' C6' Cl1' 119.5(4) . . ?
O3' C2' C3' 112.5(3) . . ?
O3' C2' C1' 108.1(4) . . ?
C3' C2' C1' 112.7(3) . . ?
O3' C2' H2' 107.8 . . ?
C3' C2' H2' 107.8 . . ?
C1' C2' H2' 107.8 . . ?
C6 C7 C8 119.7(4) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C5 C4 C3 121.5(4) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
O3 C2 C3 111.9(3) . . ?
O3 C2 C1 109.2(4) . . ?
C3 C2 C1 110.4(3) . . ?
O3 C2 H2 108.4 . . ?
C3 C2 H2 108.4 . . ?
C1 C2 H2 108.4 . . ?
O1 C1 O2 125.1(4) . . ?
O1 C1 C2 119.5(4) . . ?
O2 C1 C2 115.4(4) . . ?
C13' C12' C11' 112.3(4) . . ?
C13' C12' H12A 109.2 . . ?
C11' C12' H12A 109.2 . . ?
C13' C12' H12B 109.2 . . ?
C11' C12' H12B 109.2 . . ?
H12A C12' H12B 107.9 . . ?
C5' C4' C3' 122.1(4) . . ?
C5' C4' H4' 118.9 . . ?
C3' C4' H4' 118.9 . . ?
C16 C11 C12 110.5(3) . . ?
C16 C11 C9 114.8(4) . . ?
C12 C11 C9 109.7(4) . . ?
C16 C11 H11 107.2 . . ?
C12 C11 H11 107.2 . . ?
C9 C11 H11 107.2 . . ?
C7 C8 C3 121.0(4) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
C9' C11' C12' 112.0(3) . . ?
C9' C11' C16' 114.7(3) . . ?
C12' C11' C16' 110.6(3) . . ?
C9' C11' H11' 106.3 . . ?
C12' C11' H11' 106.3 . . ?
C16' C11' H11' 106.3 . . ?
C14' C15' C16' 110.7(4) . . ?
C14' C15' H15A 109.5 . . ?
C16' C15' H15A 109.5 . . ?
C14' C15' H15B 109.5 . . ?
C16' C15' H15B 109.5 . . ?
H15A C15' H15B 108.1 . . ?
C13 C12 C11 111.3(4) . . ?
C13 C12 H12C 109.4 . . ?
C11 C12 H12C 109.4 . . ?
C13 C12 H12D 109.4 . . ?
C11 C12 H12D 109.4 . . ?
H12C C12 H12D 108.0 . . ?
O1' C1' O2' 125.7(4) . . ?
O1' C1' C2' 117.8(4) . . ?
O2' C1' C2' 116.5(4) . . ?
C6 C5 C4 118.9(4) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
N1' C9' C11' 112.9(3) . . ?
N1' C9' C10' 107.2(4) . . ?
C11' C9' C10' 113.7(4) . . ?
N1' C9' H9' 107.6 . . ?
C11' C9' H9' 107.6 . . ?
C10' C9' H9' 107.6 . . ?
C15' C14' C13' 111.0(4) . . ?
C15' C14' H14A 109.4 . . ?
C13' C14' H14A 109.4 . . ?
C15' C14' H14B 109.4 . . ?
C13' C14' H14B 109.4 . . ?
H14A C14' H14B 108.0 . . ?
C14' C13' C12' 111.0(4) . . ?
C14' C13' H13A 109.4 . . ?
C12' C13' H13A 109.4 . . ?
C14' C13' H13B 109.4 . . ?
C12' C13' H13B 109.4 . . ?
H13A C13' H13B 108.0 . . ?
N1 C9 C10 108.3(4) . . ?
N1 C9 C11 110.9(3) . . ?
C10 C9 C11 115.4(3) . . ?
N1 C9 H9 107.3 . . ?
C10 C9 H9 107.3 . . ?
C11 C9 H9 107.3 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C15 C16 C11 111.1(4) . . ?
C15 C16 H16C 109.4 . . ?
C11 C16 H16C 109.4 . . ?
C15 C16 H16D 109.4 . . ?
C11 C16 H16D 109.4 . . ?
H16C C16 H16D 108.0 . . ?
C14 C15 C16 111.6(4) . . ?
C14 C15 H15C 109.3 . . ?
C16 C15 H15C 109.3 . . ?
C14 C15 H15D 109.3 . . ?
C16 C15 H15D 109.3 . . ?
H15C C15 H15D 108.0 . . ?
C12 C13 C14 111.1(4) . . ?
C12 C13 H13C 109.4 . . ?
C14 C13 H13C 109.4 . . ?
C12 C13 H13D 109.4 . . ?
C14 C13 H13D 109.4 . . ?
H13C C13 H13D 108.0 . . ?
C9' C10' H10D 109.5 . . ?
C9' C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
C9' C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
C13 C14 C15 111.5(4) . . ?
C13 C14 H14C 109.3 . . ?
C15 C14 H14C 109.3 . . ?
C13 C14 H14D 109.3 . . ?
C15 C14 H14D 109.3 . . ?
H14C C14 H14D 108.0 . . ?

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
C3' C8' C7' C6' 0.4(6) . . . . ?
C7' C8' C3' C4' -0.1(6) . . . . ?
C7' C8' C3' C2' 178.0(4) . . . . ?
C4' C5' C6' C7' -0.6(7) . . . . ?
C4' C5' C6' Cl1' -179.8(4) . . . . ?
C8' C7' C6' C5' 0.0(6) . . . . ?
C8' C7' C6' Cl1' 179.2(3) . . . . ?
C4' C3' C2' O3' -25.7(5) . . . . ?
C8' C3' C2' O3' 156.3(4) . . . . ?
C4' C3' C2' C1' 96.8(5) . . . . ?
C8' C3' C2' C1' -81.3(5) . . . . ?
C5 C6 C7 C8 1.8(7) . . . . ?
Cl1 C6 C7 C8 -177.9(3) . . . . ?
C8 C3 C4 C5 -0.4(6) . . . . ?
C2 C3 C4 C5 177.6(4) . . . . ?
C4 C3 C2 O3 31.7(5) . . . . ?
C8 C3 C2 O3 -150.3(4) . . . . ?
C4 C3 C2 C1 -90.1(5) . . . . ?
C8 C3 C2 C1 87.9(5) . . . . ?
O3 C2 C1 O1 7.0(5) . . . . ?
C3 C2 C1 O1 130.4(4) . . . . ?
O3 C2 C1 O2 -173.3(3) . . . . ?
C3 C2 C1 O2 -49.9(5) . . . . ?
C6' C5' C4' C3' 0.9(7) . . . . ?
C8' C3' C4' C5' -0.6(6) . . . . ?
C2' C3' C4' C5' -178.6(4) . . . . ?
C6 C7 C8 C3 -1.6(6) . . . . ?
C4 C3 C8 C7 0.9(6) . . . . ?
C2 C3 C8 C7 -177.1(4) . . . . ?
C13' C12' C11' C9' 177.4(3) . . . . ?
C13' C12' C11' C16' -53.3(4) . . . . ?
C15' C16' C11' C9' -177.6(4) . . . . ?
C15' C16' C11' C12' 54.6(5) . . . . ?
C11' C16' C15' C14' -57.1(5) . . . . ?
C16 C11 C12 C13 56.6(5) . . . . ?
C9 C11 C12 C13 -175.9(4) . . . . ?
O3' C2' C1' O1' -25.3(5) . . . . ?
C3' C2' C1' O1' -150.2(4) . . . . ?
O3' C2' C1' O2' 156.9(3) . . . . ?
C3' C2' C1' O2' 31.9(5) . . . . ?
C7 C6 C5 C4 -1.3(7) . . . . ?
Cl1 C6 C5 C4 178.4(3) . . . . ?
C3 C4 C5 C6 0.6(7) . . . . ?
C12' C11' C9' N1' 76.6(4) . . . . ?
C16' C11' C9' N1' -50.5(5) . . . . ?
C12' C11' C9' C10' -160.9(3) . . . . ?
C16' C11' C9' C10' 72.0(5) . . . . ?
C16' C15' C14' C13' 57.5(5) . . . . ?
C15' C14' C13' C12' -56.0(5) . . . . ?
C11' C12' C13' C14' 54.3(5) . . . . ?
C16 C11 C9 N1 -83.5(4) . . . . ?
C12 C11 C9 N1 151.4(4) . . . . ?
C16 C11 C9 C10 40.1(5) . . . . ?
C12 C11 C9 C10 -85.0(5) . . . . ?
C12 C11 C16 C15 -55.6(5) . . . . ?
C9 C11 C16 C15 179.8(4) . . . . ?
C11 C16 C15 C14 54.9(5) . . . . ?
C11 C12 C13 C14 -56.4(5) . . . . ?
C12 C13 C14 C15 55.3(6) . . . . ?
C16 C15 C14 C13 -54.7(5) . . . . ?

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.041



####################################################################### 
# 
# 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_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 2059731'
loop_
_audit_author_name
_audit_author_address
'Laura Bereczki'
;Research Centre for Natural Sciences
Hungary
;
_audit_update_record             
;
2021-01-29 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_chemical_name_systematic        
;
(R)-(1-cyclohexylethyl)ammonium (S)-2-(2-chlorophenyl)-2-hydroxyacetate
;
_chemical_name_common            
;
(R)-(1-cyclohexylethyl)ammonium (S)-2-chloromandelate'
;
_chemical_melting_point          398(1)
_chemical_formula_moiety         'C8 H18 N 1+, C8 H6 Cl O3 1-'
_chemical_formula_sum            'C16 H24 Cl N O3'
_chemical_formula_weight         313.81

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'
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.0572(9)
_cell_length_b                   29.711(3)
_cell_length_c                   12.6381(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.337(3)
_cell_angle_gamma                90
_cell_volume                     3395.1(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    143(2)
_cell_measurement_reflns_used    24274
_cell_measurement_theta_min      3.040
_cell_measurement_theta_max      25.300

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   0.29770
_exptl_transmission_factor_max   1.00000
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.234
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.298
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
NUMABS (T.Higashi, 2001)
;
_diffrn_ambient_temperature      143(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed Tube'
_diffrn_measurement_device_type  RAXIS-RAPID
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            45929
_diffrn_reflns_av_unetI/netI     0.1600
_diffrn_reflns_av_R_equivalents  0.1721
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.023
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             45929
_reflns_number_gt                5895
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.958
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.998
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_cell_refinement       
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_data_reduction        
;
RAPID-AUTO (Rigaku Corp., Tokyo, Japan, 2015)
;
_computing_structure_solution    
;
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Spek, A.L. (2003). J.Appl.Cryst. 36,7-13.
;
_computing_publication_material  
;
C. F. Macrae, J. Appl. Cryst., 41, 466-470, 2008
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1013P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1399 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(7)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         12376
_refine_ls_number_parameters     972
_refine_ls_number_restraints     386
_refine_ls_R_factor_all          0.1934
_refine_ls_R_factor_gt           0.0934
_refine_ls_wR_factor_ref         0.2376
_refine_ls_wR_factor_gt          0.1687
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O12 O 0.1981(7) 0.6899(2) 0.3164(7) 0.053(2) Uani 1 1 d . . . . .
H12 H 0.190978 0.715194 0.341431 0.079 Uiso 1 1 calc R U . . .
O10 O -0.0294(7) 0.7381(2) 0.3784(7) 0.062(2) Uani 1 1 d . . . . .
O11 O -0.1941(7) 0.6969(2) 0.2812(6) 0.0478(18) Uani 1 1 d . . . . .
C17 C -0.0641(12) 0.7047(3) 0.3206(9) 0.045(3) Uani 1 1 d . . . . .
C18 C 0.0551(10) 0.6704(3) 0.3017(9) 0.044(3) Uani 1 1 d . . . . .
H18 H 0.041555 0.659272 0.228772 0.053 Uiso 1 1 calc R U . A 7
Cl1 Cl 0.1844(3) 0.93903(9) 0.4866(2) 0.0607(8) Uani 1 1 d . . . . .
O2 O 0.4930(7) 0.8207(2) 0.3874(6) 0.0444(17) Uani 1 1 d . . . . .
O1 O 0.3426(7) 0.7635(2) 0.4231(6) 0.0502(19) Uani 1 1 d . . . . .
O3 O 0.1109(7) 0.8203(2) 0.4305(6) 0.052(2) Uani 1 1 d . . . . .
H3 H 0.115780 0.793181 0.419761 0.077 Uiso 1 1 calc R U . . .
C5 C 0.2624(12) 0.9151(4) 0.6866(10) 0.053(3) Uani 1 1 d . . . . .
H5 H 0.236026 0.944449 0.702766 0.063 Uiso 1 1 calc R U . . .
C4 C 0.2501(10) 0.8996(3) 0.5834(9) 0.047(3) Uani 1 1 d . . . . .
C1 C 0.3733(11) 0.8044(3) 0.4151(8) 0.042(3) Uani 1 1 d . . . . .
C6 C 0.3137(13) 0.8866(4) 0.7636(10) 0.062(3) Uani 1 1 d . . . . .
H6 H 0.324760 0.896658 0.833263 0.075 Uiso 1 1 calc R U . . .
C8 C 0.3341(12) 0.8283(4) 0.6363(11) 0.059(3) Uani 1 1 d . . . . .
H8 H 0.358865 0.798679 0.621113 0.071 Uiso 1 1 calc R U . . .
C3 C 0.2821(10) 0.8561(3) 0.5517(9) 0.039(3) Uani 1 1 d . . . . .
C2 C 0.2568(10) 0.8388(3) 0.4403(9) 0.040(3) Uani 1 1 d . . . . .
H2 H 0.262348 0.864147 0.391000 0.047 Uiso 1 1 calc R U . . .
C7 C 0.3502(13) 0.8425(4) 0.7402(11) 0.065(3) Uani 1 1 d . . . . .
H7 H 0.384742 0.822938 0.793529 0.078 Uiso 1 1 calc R U . . .
O6 O 1.1874(7) 0.8585(2) 0.1906(6) 0.054(2) Uani 1 1 d . . . . .
H6A H 1.175738 0.833209 0.165221 0.082 Uiso 1 1 calc R U . . .
O4 O 0.9387(7) 0.8136(2) 0.1221(6) 0.052(2) Uani 1 1 d . . . . .
O5 O 0.8025(7) 0.8537(2) 0.2292(5) 0.0434(17) Uani 1 1 d . . . . .
C9 C 0.9179(11) 0.8453(3) 0.1845(9) 0.040(3) Uani 1 1 d . . . . .
C10 C 1.0469(11) 0.8785(3) 0.2040(9) 0.043(3) Uani 1 1 d . . . . .
H10 H 1.044189 0.892019 0.274588 0.051 Uiso 1 1 calc R U . B 5
O9 O 0.0698(7) 0.7316(2) 1.0895(6) 0.0494(19) Uani 1 1 d . . . . .
H9 H 0.075956 0.759004 1.095640 0.074 Uiso 1 1 calc R U . . .
O7 O 0.3150(7) 0.7862(2) 1.0946(6) 0.0510(19) Uani 1 1 d . . . . .
O8 O 0.4580(7) 0.7256(2) 1.1229(5) 0.0441(18) Uani 1 1 d . . . . .
C25 C 0.3375(10) 0.7450(3) 1.0965(8) 0.038(2) Uani 1 1 d . . . . .
C26 C 0.2076(10) 0.7141(3) 1.0598(9) 0.045(3) Uani 1 1 d . . . . .
H26 H 0.223134 0.683320 1.086351 0.054 Uiso 1 1 calc R U . C 3
N2 N 0.7890(8) 0.8073(2) 0.4283(6) 0.040(2) Uani 1 1 d . . . . .
H2A H 0.692070 0.806173 0.412450 0.060 Uiso 1 1 calc R U . . .
H2B H 0.831081 0.782110 0.406706 0.060 Uiso 1 1 calc R U . . .
H2C H 0.827416 0.830800 0.395819 0.060 Uiso 1 1 calc R U . . .
C42 C 0.8167(11) 0.8121(3) 0.5447(9) 0.047(3) Uani 1 1 d . . . . .
H42 H 0.924148 0.813018 0.559261 0.056 Uiso 1 1 calc R U . . .
C41 C 0.7599(15) 0.7698(4) 0.5977(11) 0.078(4) Uani 1 1 d . . . . .
H41A H 0.805996 0.743768 0.569040 0.118 Uiso 1 1 calc R U . . .
H41B H 0.654677 0.767772 0.584681 0.118 Uiso 1 1 calc R U . . .
H41C H 0.783485 0.771313 0.672667 0.118 Uiso 1 1 calc R U . . .
N3 N 0.5171(8) 0.6947(2) 0.3362(6) 0.038(2) Uani 1 1 d . . . . .
H3A H 0.466919 0.692431 0.273721 0.056 Uiso 1 1 calc R U . . .
H3B H 0.612378 0.699237 0.326034 0.056 Uiso 1 1 calc R U . . .
H3C H 0.482180 0.717695 0.372225 0.056 Uiso 1 1 calc R U . . .
C52 C 0.5230(15) 0.5677(4) 0.3989(10) 0.067(4) Uani 1 1 d . . . . .
H52A H 0.571074 0.568699 0.469473 0.080 Uiso 1 1 calc R U . . .
H52B H 0.417216 0.565626 0.406186 0.080 Uiso 1 1 calc R U . . .
C50 C 0.4999(12) 0.6517(3) 0.3981(8) 0.043(3) Uani 1 1 d . . . . .
H50 H 0.393868 0.646946 0.405297 0.052 Uiso 1 1 calc R U . . .
C53 C 0.5746(16) 0.5264(4) 0.3419(12) 0.082(4) Uani 1 1 d . . . . .
H53A H 0.546326 0.499720 0.379994 0.099 Uiso 1 1 calc R U . . .
H53B H 0.681697 0.526855 0.341453 0.099 Uiso 1 1 calc R U . . .
C49 C 0.5713(13) 0.6591(4) 0.5090(9) 0.065(3) Uani 1 1 d . . . . .
H49A H 0.525578 0.684384 0.541274 0.098 Uiso 1 1 calc R U . . .
H49B H 0.674960 0.664908 0.504283 0.098 Uiso 1 1 calc R U . . .
H49C H 0.558244 0.632692 0.551164 0.098 Uiso 1 1 calc R U . . .
C54 C 0.509(2) 0.5239(4) 0.2272(12) 0.095(5) Uani 1 1 d . . . . .
H54A H 0.547854 0.497717 0.192352 0.114 Uiso 1 1 calc R U . . .
H54B H 0.402210 0.520688 0.227257 0.114 Uiso 1 1 calc R U . . .
C51 C 0.5577(12) 0.6117(3) 0.3391(9) 0.050(3) Uani 1 1 d . . . . .
H51 H 0.665337 0.614614 0.337453 0.060 Uiso 1 1 calc R U . . .
C56 C 0.4930(15) 0.6081(4) 0.2257(10) 0.069(4) Uani 1 1 d . . . . .
H56A H 0.519781 0.634797 0.186930 0.083 Uiso 1 1 calc R U . . .
H56B H 0.386019 0.607230 0.226283 0.083 Uiso 1 1 calc R U . . .
C55 C 0.547(2) 0.5661(4) 0.1674(11) 0.098(5) Uani 1 1 d . . . . .
H55A H 0.500342 0.564987 0.096327 0.117 Uiso 1 1 calc R U . . .
H55B H 0.653063 0.567745 0.161616 0.117 Uiso 1 1 calc R U . . .
N1 N 0.5067(8) 0.8551(2) 0.1754(7) 0.038(2) Uani 1 1 d . . . . .
H1A H 0.603146 0.849894 0.186885 0.057 Uiso 1 1 calc R U . . .
H1B H 0.464627 0.831701 0.141431 0.057 Uiso 1 1 calc R U . . .
H1C H 0.465855 0.858856 0.237130 0.057 Uiso 1 1 calc R U . . .
C36 C 0.4822(16) 0.9808(3) 0.1107(10) 0.074(4) Uani 1 1 d . . . . .
H36A H 0.376046 0.979841 0.095241 0.089 Uiso 1 1 calc R U . . .
H36B H 0.529295 0.980876 0.043701 0.089 Uiso 1 1 calc R U . . .
C35 C 0.5295(12) 0.9389(3) 0.1726(8) 0.048(3) Uani 1 1 d . . . . .
H35 H 0.637544 0.939217 0.183136 0.058 Uiso 1 1 calc R U . . .
C33 C 0.5701(12) 0.8915(4) 0.0097(9) 0.053(3) Uani 1 1 d . . . . .
H33A H 0.535032 0.865403 -0.029054 0.080 Uiso 1 1 calc R U . . .
H33B H 0.673416 0.887961 0.029372 0.080 Uiso 1 1 calc R U . . .
H33C H 0.555799 0.917731 -0.033911 0.080 Uiso 1 1 calc R U . . .
C34 C 0.4842(11) 0.8967(3) 0.1093(8) 0.044(3) Uani 1 1 d . . . . .
H34 H 0.378782 0.899025 0.087782 0.053 Uiso 1 1 calc R U . . .
C40 C 0.4637(13) 0.9402(4) 0.2824(9) 0.058(3) Uani 1 1 d . . . . .
H40A H 0.356952 0.937509 0.273659 0.070 Uiso 1 1 calc R U . . .
H40B H 0.500741 0.914760 0.324093 0.070 Uiso 1 1 calc R U . . .
C37 C 0.522(2) 1.0247(4) 0.1708(12) 0.097(5) Uani 1 1 d . . . . .
H37A H 0.628806 1.027439 0.180603 0.117 Uiso 1 1 calc R U . . .
H37B H 0.485272 1.050355 0.129786 0.117 Uiso 1 1 calc R U . . .
C38 C 0.455(2) 1.0245(4) 0.2777(13) 0.104(5) Uani 1 1 d . . . . .
H38A H 0.484496 1.051472 0.316474 0.125 Uiso 1 1 calc R U . . .
H38B H 0.347852 1.024572 0.267492 0.125 Uiso 1 1 calc R U . . .
C39 C 0.5035(16) 0.9837(4) 0.3411(11) 0.081(4) Uani 1 1 d . . . . .
H39A H 0.456840 0.983944 0.408235 0.097 Uiso 1 1 calc R U . . .
H39B H 0.609753 0.984893 0.355980 0.097 Uiso 1 1 calc R U . . .
N4 N 0.7471(8) 0.7399(2) 1.0801(6) 0.039(2) Uani 1 1 d . . . . .
H4A H 0.799059 0.718553 1.114828 0.059 Uiso 1 1 calc R U . . .
H4B H 0.654259 0.739425 1.099568 0.059 Uiso 1 1 calc R U . . .
H4C H 0.787080 0.766648 1.095163 0.059 Uiso 1 1 calc R U . . .
C57 C 0.6516(13) 0.7673(4) 0.9084(9) 0.063(3) Uani 1 1 d . . . . .
H57A H 0.551300 0.763119 0.927092 0.094 Uiso 1 1 calc R U . . .
H57B H 0.656291 0.765231 0.832883 0.094 Uiso 1 1 calc R U . . .
H57C H 0.685688 0.796455 0.931865 0.094 Uiso 1 1 calc R U . . .
C58 C 0.7486(11) 0.7313(3) 0.9611(8) 0.046(3) Uani 1 1 d . . . . .
H58 H 0.849375 0.738511 0.942266 0.055 Uiso 1 1 calc R U . D 1
C59' C 0.727(3) 0.6843(7) 0.9338(14) 0.040(6) Uani 0.619(16) 1 d D U P E 1
H59' H 0.624360 0.676802 0.945787 0.048 Uiso 0.619(16) 1 calc R U P E 1
C60' C 0.826(2) 0.6507(5) 0.9978(16) 0.051(6) Uani 0.619(16) 1 d D U P E 1
H60C H 0.928152 0.659604 0.993407 0.061 Uiso 0.619(16) 1 calc R U P E 1
H60D H 0.802398 0.652504 1.071663 0.061 Uiso 0.619(16) 1 calc R U P E 1
C61' C 0.809(2) 0.6023(6) 0.9614(14) 0.059(6) Uani 0.619(16) 1 d D U P E 1
H61C H 0.708643 0.592148 0.970958 0.071 Uiso 0.619(16) 1 calc R U P E 1
H61D H 0.876057 0.583289 1.003830 0.071 Uiso 0.619(16) 1 calc R U P E 1
C62' C 0.842(2) 0.5983(7) 0.8450(16) 0.066(6) Uani 0.619(16) 1 d D U P E 1
H62C H 0.828700 0.567406 0.821682 0.080 Uiso 0.619(16) 1 calc R U P E 1
H62D H 0.943937 0.606817 0.835800 0.080 Uiso 0.619(16) 1 calc R U P E 1
C63' C 0.737(2) 0.6294(6) 0.7779(14) 0.054(6) Uani 0.619(16) 1 d D U P E 1
H63C H 0.760978 0.627456 0.704209 0.065 Uiso 0.619(16) 1 calc R U P E 1
H63D H 0.636220 0.619067 0.782887 0.065 Uiso 0.619(16) 1 calc R U P E 1
C64' C 0.748(3) 0.6788(6) 0.8139(15) 0.054(6) Uani 0.619(16) 1 d D U P E 1
H64C H 0.672981 0.696252 0.774335 0.065 Uiso 0.619(16) 1 calc R U P E 1
H64D H 0.843895 0.690656 0.797800 0.065 Uiso 0.619(16) 1 calc R U P E 1
C59 C 0.662(4) 0.6849(12) 0.939(2) 0.051(11) Uani 0.381(16) 1 d D U P E 2
H59 H 0.560149 0.688465 0.959091 0.061 Uiso 0.381(16) 1 calc R U P E 2
C60 C 0.733(3) 0.6452(10) 1.002(3) 0.054(10) Uani 0.381(16) 1 d D U P E 2
H60A H 0.668154 0.619321 0.996027 0.065 Uiso 0.381(16) 1 calc R U P E 2
H60B H 0.745373 0.653440 1.076294 0.065 Uiso 0.381(16) 1 calc R U P E 2
C61 C 0.886(3) 0.6326(11) 0.961(2) 0.045(8) Uani 0.381(16) 1 d D U P E 2
H61A H 0.953907 0.657482 0.974602 0.055 Uiso 0.381(16) 1 calc R U P E 2
H61B H 0.924964 0.606760 1.000222 0.055 Uiso 0.381(16) 1 calc R U P E 2
C62 C 0.880(3) 0.6215(10) 0.841(2) 0.045(8) Uani 0.381(16) 1 d D U P E 2
H62A H 0.823343 0.594239 0.827770 0.054 Uiso 0.381(16) 1 calc R U P E 2
H62B H 0.979384 0.616658 0.818751 0.054 Uiso 0.381(16) 1 calc R U P E 2
C63 C 0.807(3) 0.6613(11) 0.779(2) 0.045(9) Uani 0.381(16) 1 d D U P E 2
H63A H 0.872746 0.687038 0.784060 0.054 Uiso 0.381(16) 1 calc R U P E 2
H63B H 0.793251 0.653019 0.704898 0.054 Uiso 0.381(16) 1 calc R U P E 2
C64 C 0.659(3) 0.6745(10) 0.820(2) 0.045(9) Uani 0.381(16) 1 d D U P E 2
H64A H 0.589032 0.650274 0.804289 0.054 Uiso 0.381(16) 1 calc R U P E 2
H64B H 0.622594 0.700868 0.780866 0.054 Uiso 0.381(16) 1 calc R U P E 2
C27 C 0.197(3) 0.7151(7) 0.9360(13) 0.054(9) Uani 0.52(3) 1 d G U P F 3
C28 C 0.251(3) 0.6785(7) 0.8819(18) 0.062(8) Uani 0.52(3) 1 d G U P F 3
C29 C 0.249(3) 0.6790(8) 0.7719(18) 0.083(10) Uani 0.52(3) 1 d G U P F 3
H29 H 0.284907 0.654461 0.735642 0.100 Uiso 0.52(3) 1 calc R U P F 3
C30 C 0.193(3) 0.7162(9) 0.7159(12) 0.081(10) Uani 0.52(3) 1 d G U P F 3
H30 H 0.191851 0.716493 0.642322 0.097 Uiso 0.52(3) 1 calc R U P F 3
C31 C 0.139(3) 0.7528(7) 0.7701(15) 0.078(9) Uani 0.52(3) 1 d G U P F 3
H31 H 0.101799 0.777679 0.732674 0.094 Uiso 0.52(3) 1 calc R U P F 3
C32 C 0.141(2) 0.7523(6) 0.8801(15) 0.067(8) Uani 0.52(3) 1 d G U P F 3
H32 H 0.104801 0.776834 0.916348 0.080 Uiso 0.52(3) 1 calc R U P F 3
Cl4 Cl 0.3172(10) 0.6290(3) 0.9421(12) 0.078(4) Uani 0.52(3) 1 d . U P F 3
C27' C 0.220(3) 0.7035(8) 0.9432(13) 0.037(7) Uani 0.48(3) 1 d G U P F 4
C28' C 0.270(3) 0.6627(7) 0.9051(17) 0.074(10) Uani 0.48(3) 1 d G U P F 4
C29' C 0.278(3) 0.6562(8) 0.7967(18) 0.091(11) Uani 0.48(3) 1 d G U P F 4
H29' H 0.311643 0.628924 0.771147 0.109 Uiso 0.48(3) 1 calc R U P F 4
C30' C 0.236(3) 0.6905(9) 0.7263(13) 0.069(10) Uani 0.48(3) 1 d G U P F 4
H30' H 0.241116 0.686094 0.653798 0.083 Uiso 0.48(3) 1 calc R U P F 4
C31' C 0.186(3) 0.7312(8) 0.7645(16) 0.078(10) Uani 0.48(3) 1 d G U P F 4
H31' H 0.157418 0.754162 0.717429 0.094 Uiso 0.48(3) 1 calc R U P F 4
C32' C 0.178(3) 0.7378(7) 0.8729(17) 0.057(8) Uani 0.48(3) 1 d G U P F 4
H32' H 0.144246 0.765061 0.898410 0.069 Uiso 0.48(3) 1 calc R U P F 4
Cl4' Cl 0.2999(12) 0.6179(4) 0.9885(13) 0.086(4) Uani 0.48(3) 1 d . U P F 4
Cl2 Cl 0.9464(16) 0.9721(3) 0.2760(10) 0.082(3) Uani 0.70(4) 1 d . U P G 5
C11' C 1.0305(19) 0.9139(5) 0.1199(11) 0.058(6) Uani 0.70(4) 1 d G U P G 5
C12' C 0.982(2) 0.9564(5) 0.1482(12) 0.055(6) Uani 0.70(4) 1 d G U P G 5
C13' C 0.962(2) 0.9897(5) 0.0715(16) 0.085(7) Uani 0.70(4) 1 d G U P G 5
H13' H 0.930005 1.018207 0.090434 0.102 Uiso 0.70(4) 1 calc R U P G 5
C14' C 0.990(2) 0.9806(6) -0.0333(14) 0.088(8) Uani 0.70(4) 1 d G U P G 5
H14' H 0.976334 1.002870 -0.084551 0.106 Uiso 0.70(4) 1 calc R U P G 5
C15' C 1.038(2) 0.9380(7) -0.0615(11) 0.084(7) Uani 0.70(4) 1 d G U P G 5
H15' H 1.056558 0.931875 -0.131675 0.101 Uiso 0.70(4) 1 calc R U P G 5
C16' C 1.0583(18) 0.9047(6) 0.0151(12) 0.063(6) Uani 0.70(4) 1 d G U P G 5
H16' H 1.090452 0.876216 -0.003814 0.075 Uiso 0.70(4) 1 calc R U P G 5
Cl2' Cl 0.907(3) 0.9659(6) 0.2977(16) 0.052(6) Uani 0.30(4) 1 d . U P G 6
C11 C 1.006(4) 0.9238(10) 0.137(2) 0.007(9) Uani 0.30(4) 1 d G U P G 6
C12 C 0.946(4) 0.9631(10) 0.176(2) 0.043(12) Uani 0.30(4) 1 d G U P G 6
C13 C 0.918(5) 0.9995(10) 0.109(3) 0.063(14) Uani 0.30(4) 1 d G U P G 6
H13 H 0.877841 1.025814 0.134981 0.076 Uiso 0.30(4) 1 calc R U P G 6
C14 C 0.950(5) 0.9968(13) 0.003(3) 0.080(18) Uani 0.30(4) 1 d G U P G 6
H14 H 0.930992 1.021152 -0.042056 0.096 Uiso 0.30(4) 1 calc R U P G 6
C15 C 1.010(6) 0.9575(16) -0.036(2) 0.082(19) Uani 0.30(4) 1 d G U P G 6
H15 H 1.031358 0.955621 -0.107214 0.099 Uiso 0.30(4) 1 calc R U P G 6
C16 C 1.038(5) 0.9210(13) 0.031(2) 0.080(18) Uani 0.30(4) 1 d G U P G 6
H16 H 1.078573 0.894751 0.004665 0.096 Uiso 0.30(4) 1 calc R U P G 6
Cl3 Cl -0.021(3) 0.5720(2) 0.2193(7) 0.086(4) Uani 0.64(4) 1 d . U P H 7
C19 C 0.043(2) 0.6300(5) 0.3794(12) 0.072(12) Uani 0.64(4) 1 d G U P H 7
C20 C 0.003(2) 0.5862(5) 0.3516(11) 0.043(5) Uani 0.64(4) 1 d G U P H 7
C21 C -0.020(2) 0.5546(4) 0.4300(15) 0.060(7) Uani 0.64(4) 1 d G U P H 7
H21 H -0.047182 0.525281 0.411319 0.072 Uiso 0.64(4) 1 calc R U P H 7
C22 C -0.003(2) 0.5667(6) 0.5362(13) 0.081(8) Uani 0.64(4) 1 d G U P H 7
H22 H -0.018099 0.545488 0.588626 0.097 Uiso 0.64(4) 1 calc R U P H 7
C23 C 0.038(2) 0.6104(6) 0.5640(10) 0.072(7) Uani 0.64(4) 1 d G U P H 7
H23 H 0.049173 0.618515 0.635115 0.087 Uiso 0.64(4) 1 calc R U P H 7
C24 C 0.060(2) 0.6421(4) 0.4857(14) 0.051(6) Uani 0.64(4) 1 d G U P H 7
H24 H 0.087363 0.671335 0.504298 0.061 Uiso 0.64(4) 1 calc R U P H 7
Cl3' Cl 0.074(4) 0.5785(7) 0.2009(17) 0.090(8) Uani 0.36(4) 1 d . U P H 8
C19' C 0.034(3) 0.6334(6) 0.3781(17) 0.004(9) Uani 0.36(4) 1 d G U P H 8
C20' C 0.051(4) 0.5913(8) 0.3323(18) 0.062(14) Uani 0.36(4) 1 d G U P H 8
C21' C 0.043(4) 0.5527(6) 0.394(3) 0.070(13) Uani 0.36(4) 1 d G U P H 8
H21' H 0.053316 0.524489 0.363181 0.083 Uiso 0.36(4) 1 calc R U P H 8
C22' C 0.019(4) 0.5562(9) 0.501(3) 0.069(13) Uani 0.36(4) 1 d G U P H 8
H22' H 0.013434 0.530351 0.542333 0.082 Uiso 0.36(4) 1 calc R U P H 8
C23' C 0.003(4) 0.5983(12) 0.5470(19) 0.088(17) Uani 0.36(4) 1 d G U P H 8
H23' H -0.013277 0.600654 0.618791 0.106 Uiso 0.36(4) 1 calc R U P H 8
C24' C 0.011(4) 0.6369(8) 0.4854(18) 0.048(12) Uani 0.36(4) 1 d G U P H 8
H24' H -0.000106 0.665095 0.516098 0.057 Uiso 0.36(4) 1 calc R U P H 8
C43 C 0.7542(12) 0.8562(4) 0.5854(9) 0.058(3) Uani 1 1 d D . . . .
H43 H 0.646065 0.854305 0.578554 0.070 Uiso 1 1 calc R U . . .
C44 C 0.8013(14) 0.8966(3) 0.5212(9) 0.061(3) Uani 1 1 d D . . . .
H44A H 0.758260 0.892251 0.449826 0.074 Uiso 1 1 calc R U . I 9
H44B H 0.907538 0.894138 0.516731 0.074 Uiso 1 1 calc R U . I 9
C45' C 0.771(4) 0.9458(8) 0.550(3) 0.058(9) Uani 0.49(6) 1 d D U P J 9
H45A H 0.827537 0.965954 0.507810 0.069 Uiso 0.49(6) 1 calc R U P J 9
H45B H 0.666518 0.952670 0.537168 0.069 Uiso 0.49(6) 1 calc R U P J 9
C46' C 0.816(4) 0.9508(11) 0.665(3) 0.084(13) Uani 0.49(6) 1 d D U P J 9
H46A H 0.786350 0.980196 0.689761 0.100 Uiso 0.49(6) 1 calc R U P J 9
H46B H 0.922637 0.948557 0.675381 0.100 Uiso 0.49(6) 1 calc R U P J 9
C47' C 0.744(3) 0.9142(8) 0.730(3) 0.050(9) Uani 0.49(6) 1 d D U P J 9
H47A H 0.637277 0.915673 0.716870 0.060 Uiso 0.49(6) 1 calc R U P J 9
H47B H 0.765262 0.920174 0.805096 0.060 Uiso 0.49(6) 1 calc R U P J 9
C45 C 0.737(4) 0.9363(12) 0.582(3) 0.086(11) Uani 0.51(6) 1 d D U P J 10
H45C H 0.753223 0.963701 0.542741 0.103 Uiso 0.51(6) 1 calc R U P J 10
H45D H 0.631155 0.932019 0.583802 0.103 Uiso 0.51(6) 1 calc R U P J 10
C46 C 0.799(4) 0.9428(8) 0.694(2) 0.069(10) Uani 0.51(6) 1 d D U P J 10
H46C H 0.758718 0.970126 0.722530 0.083 Uiso 0.51(6) 1 calc R U P J 10
H46D H 0.905757 0.946279 0.693712 0.083 Uiso 0.51(6) 1 calc R U P J 10
C47 C 0.762(5) 0.9021(11) 0.764(3) 0.129(16) Uani 0.51(6) 1 d D U P J 10
H47C H 0.818903 0.903178 0.831630 0.155 Uiso 0.51(6) 1 calc R U P J 10
H47D H 0.657241 0.901932 0.777919 0.155 Uiso 0.51(6) 1 calc R U P J 10
C48 C 0.8004(16) 0.8626(4) 0.7033(10) 0.090(5) Uani 1 1 d D . . . .
H48A H 0.906824 0.859979 0.715610 0.108 Uiso 1 1 calc R U . J 9
H48B H 0.752986 0.840461 0.746480 0.108 Uiso 1 1 calc R U . J 9


_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
O12 C18 1.421(11) . ?
O12 H12 0.8200 . ?
O10 C17 1.261(12) . ?
O11 C17 1.273(12) . ?
C17 C18 1.515(14) . ?
C18 C19' 1.48(2) . ?
C18 C19 1.559(15) . ?
C18 H18 0.9800 . ?
Cl1 C4 1.772(10) . ?
O2 C1 1.256(11) . ?
O1 C1 1.253(11) . ?
O3 C2 1.430(10) . ?
O3 H3 0.8200 . ?
C5 C6 1.352(16) . ?
C5 C4 1.382(15) . ?
C5 H5 0.9300 . ?
C4 C3 1.387(13) . ?
C1 C2 1.516(13) . ?
C6 C7 1.386(16) . ?
C6 H6 0.9300 . ?
C8 C7 1.380(16) . ?
C8 C3 1.411(15) . ?
C8 H8 0.9300 . ?
C3 C2 1.504(14) . ?
C2 H2 0.9800 . ?
C7 H7 0.9300 . ?
O6 C10 1.423(11) . ?
O6 H6A 0.8200 . ?
O4 C9 1.251(12) . ?
O5 C9 1.241(12) . ?
C9 C10 1.536(13) . ?
C10 C11' 1.497(14) . ?
C10 C11 1.62(3) . ?
C10 H10 0.9800 . ?
O9 C26 1.423(11) . ?
O9 H9 0.8200 . ?
O7 C25 1.241(11) . ?
O8 C25 1.262(11) . ?
C25 C26 1.543(13) . ?
C26 C27' 1.517(19) . ?
C26 C27 1.562(19) . ?
C26 H26 0.9800 . ?
N2 C42 1.486(13) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
C42 C41 1.527(14) . ?
C42 C43 1.529(15) . ?
C42 H42 0.9800 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
N3 C50 1.511(11) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
C52 C53 1.511(16) . ?
C52 C51 1.551(14) . ?
C52 H52A 0.9700 . ?
C52 H52B 0.9700 . ?
C50 C51 1.513(14) . ?
C50 C49 1.524(14) . ?
C50 H50 0.9800 . ?
C53 C54 1.536(19) . ?
C53 H53A 0.9700 . ?
C53 H53B 0.9700 . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C54 C55 1.514(17) . ?
C54 H54A 0.9700 . ?
C54 H54B 0.9700 . ?
C51 C56 1.521(16) . ?
C51 H51 0.9800 . ?
C56 C55 1.544(15) . ?
C56 H56A 0.9700 . ?
C56 H56B 0.9700 . ?
C55 H55A 0.9700 . ?
C55 H55B 0.9700 . ?
N1 C34 1.499(11) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C36 C35 1.518(14) . ?
C36 C37 1.542(16) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C35 C34 1.532(13) . ?
C35 C40 1.542(14) . ?
C35 H35 0.9800 . ?
C33 C34 1.526(14) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 H34 0.9800 . ?
C40 C39 1.523(15) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C37 C38 1.514(18) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.505(18) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
N4 C58 1.526(12) . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 H4C 0.8900 . ?
C57 C58 1.513(14) . ?
C57 H57A 0.9600 . ?
C57 H57B 0.9600 . ?
C57 H57C 0.9600 . ?
C58 C59' 1.45(2) . ?
C58 C59 1.60(4) . ?
C58 H58 0.9800 . ?
C59' C60' 1.54(2) . ?
C59' C64' 1.55(2) . ?
C59' H59' 0.9800 . ?
C60' C61' 1.516(19) . ?
C60' H60C 0.9700 . ?
C60' H60D 0.9700 . ?
C61' C62' 1.52(2) . ?
C61' H61C 0.9700 . ?
C61' H61D 0.9700 . ?
C62' C63' 1.54(2) . ?
C62' H62C 0.9700 . ?
C62' H62D 0.9700 . ?
C63' C64' 1.54(2) . ?
C63' H63C 0.9700 . ?
C63' H63D 0.9700 . ?
C64' H64C 0.9700 . ?
C64' H64D 0.9700 . ?
C59 C64 1.53(3) . ?
C59 C60 1.54(3) . ?
C59 H59 0.9800 . ?
C60 C61 1.55(3) . ?
C60 H60A 0.9700 . ?
C60 H60B 0.9700 . ?
C61 C62 1.54(2) . ?
C61 H61A 0.9700 . ?
C61 H61B 0.9700 . ?
C62 C63 1.55(2) . ?
C62 H62A 0.9700 . ?
C62 H62B 0.9700 . ?
C63 C64 1.52(2) . ?
C63 H63A 0.9700 . ?
C63 H63B 0.9700 . ?
C64 H64A 0.9700 . ?
C64 H64B 0.9700 . ?
C27 C28 1.3900 . ?
C27 C32 1.3900 . ?
C28 C29 1.3900 . ?
C28 Cl4 1.746(17) . ?
C29 C30 1.3900 . ?
C29 H29 0.9300 . ?
C30 C31 1.3900 . ?
C30 H30 0.9300 . ?
C31 C32 1.3900 . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C27' C28' 1.3900 . ?
C27' C32' 1.3900 . ?
C28' C29' 1.3900 . ?
C28' Cl4' 1.710(19) . ?
C29' C30' 1.3900 . ?
C29' H29' 0.9300 . ?
C30' C31' 1.3900 . ?
C30' H30' 0.9300 . ?
C31' C32' 1.3900 . ?
C31' H31' 0.9300 . ?
C32' H32' 0.9300 . ?
Cl2 C12' 1.731(14) . ?
C11' C12' 1.3900 . ?
C11' C16' 1.3900 . ?
C12' C13' 1.3900 . ?
C13' C14' 1.3900 . ?
C13' H13' 0.9300 . ?
C14' C15' 1.3900 . ?
C14' H14' 0.9300 . ?
C15' C16' 1.3900 . ?
C15' H15' 0.9300 . ?
C16' H16' 0.9300 . ?
Cl2' C12 1.60(3) . ?
C11 C12 1.3900 . ?
C11 C16 1.3900 . ?
C12 C13 1.3900 . ?
C13 C14 1.3900 . ?
C13 H13 0.9300 . ?
C14 C15 1.3900 . ?
C14 H14 0.9300 . ?
C15 C16 1.3900 . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
Cl3 C20 1.725(15) . ?
C19 C20 1.3900 . ?
C19 C24 1.3900 . ?
C20 C21 1.3900 . ?
C21 C22 1.3900 . ?
C21 H21 0.9300 . ?
C22 C23 1.3900 . ?
C22 H22 0.9300 . ?
C23 C24 1.3900 . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
Cl3' C20' 1.73(3) . ?
C19' C20' 1.3900 . ?
C19' C24' 1.3900 . ?
C20' C21' 1.3900 . ?
C21' C22' 1.3900 . ?
C21' H21' 0.9300 . ?
C22' C23' 1.3900 . ?
C22' H22' 0.9300 . ?
C23' C24' 1.3900 . ?
C23' H23' 0.9300 . ?
C24' H24' 0.9300 . ?
C43 C44 1.524(14) . ?
C43 C48 1.536(14) . ?
C43 H43 0.9800 . ?
C44 C45' 1.53(2) . ?
C44 C45 1.54(2) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C45' C46' 1.50(2) . ?
C45' H45A 0.9700 . ?
C45' H45B 0.9700 . ?
C46' C47' 1.53(3) . ?
C46' H46A 0.9700 . ?
C46' H46B 0.9700 . ?
C47' C48 1.66(2) . ?
C47' H47A 0.9700 . ?
C47' H47B 0.9700 . ?
C45 C46 1.50(2) . ?
C45 H45C 0.9700 . ?
C45 H45D 0.9700 . ?
C46 C47 1.55(3) . ?
C46 H46C 0.9700 . ?
C46 H46D 0.9700 . ?
C47 C48 1.46(2) . ?
C47 H47C 0.9700 . ?
C47 H47D 0.9700 . ?
C48 H48A 0.9700 . ?
C48 H48B 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
C18 O12 H12 109.5 . . ?
O10 C17 O11 124.3(9) . . ?
O10 C17 C18 117.8(10) . . ?
O11 C17 C18 117.8(10) . . ?
O12 C18 C19' 111.4(12) . . ?
O12 C18 C17 110.9(8) . . ?
C19' C18 C17 106.2(12) . . ?
O12 C18 C19 109.2(10) . . ?
C17 C18 C19 110.0(10) . . ?
O12 C18 H18 108.9 . . ?
C17 C18 H18 108.9 . . ?
C19 C18 H18 108.9 . . ?
C2 O3 H3 109.5 . . ?
C6 C5 C4 118.4(11) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C5 C4 C3 125.2(10) . . ?
C5 C4 Cl1 115.8(9) . . ?
C3 C4 Cl1 119.0(9) . . ?
O1 C1 O2 126.6(9) . . ?
O1 C1 C2 118.5(9) . . ?
O2 C1 C2 115.0(9) . . ?
C5 C6 C7 121.0(12) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C7 C8 C3 123.6(11) . . ?
C7 C8 H8 118.2 . . ?
C3 C8 H8 118.2 . . ?
C4 C3 C8 113.2(11) . . ?
C4 C3 C2 124.4(9) . . ?
C8 C3 C2 122.3(9) . . ?
O3 C2 C3 107.6(8) . . ?
O3 C2 C1 112.0(8) . . ?
C3 C2 C1 110.9(8) . . ?
O3 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
C1 C2 H2 108.8 . . ?
C8 C7 C6 118.6(12) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C10 O6 H6A 109.5 . . ?
O5 C9 O4 126.8(9) . . ?
O5 C9 C10 116.8(10) . . ?
O4 C9 C10 116.3(10) . . ?
O6 C10 C11' 105.1(10) . . ?
O6 C10 C9 113.0(8) . . ?
C11' C10 C9 107.0(10) . . ?
O6 C10 C11 117.4(14) . . ?
C9 C10 C11 107.5(13) . . ?
O6 C10 H10 110.5 . . ?
C11' C10 H10 110.5 . . ?
C9 C10 H10 110.5 . . ?
C26 O9 H9 109.5 . . ?
O7 C25 O8 126.5(9) . . ?
O7 C25 C26 117.5(9) . . ?
O8 C25 C26 116.0(9) . . ?
O9 C26 C27' 116.6(13) . . ?
O9 C26 C25 111.6(8) . . ?
C27' C26 C25 108.4(11) . . ?
O9 C26 C27 104.5(12) . . ?
C25 C26 C27 106.9(11) . . ?
O9 C26 H26 111.2 . . ?
C25 C26 H26 111.2 . . ?
C27 C26 H26 111.2 . . ?
C42 N2 H2A 109.5 . . ?
C42 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C42 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
N2 C42 C41 108.3(9) . . ?
N2 C42 C43 111.8(8) . . ?
C41 C42 C43 114.7(10) . . ?
N2 C42 H42 107.2 . . ?
C41 C42 H42 107.2 . . ?
C43 C42 H42 107.2 . . ?
C42 C41 H41A 109.5 . . ?
C42 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C42 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C50 N3 H3A 109.5 . . ?
C50 N3 H3B 109.5 . . ?
H3A N3 H3B 109.5 . . ?
C50 N3 H3C 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C53 C52 C51 112.0(10) . . ?
C53 C52 H52A 109.2 . . ?
C51 C52 H52A 109.2 . . ?
C53 C52 H52B 109.2 . . ?
C51 C52 H52B 109.2 . . ?
H52A C52 H52B 107.9 . . ?
N3 C50 C51 111.1(8) . . ?
N3 C50 C49 107.7(8) . . ?
C51 C50 C49 115.2(9) . . ?
N3 C50 H50 107.5 . . ?
C51 C50 H50 107.5 . . ?
C49 C50 H50 107.5 . . ?
C52 C53 C54 112.1(11) . . ?
C52 C53 H53A 109.2 . . ?
C54 C53 H53A 109.2 . . ?
C52 C53 H53B 109.2 . . ?
C54 C53 H53B 109.2 . . ?
H53A C53 H53B 107.9 . . ?
C50 C49 H49A 109.5 . . ?
C50 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C50 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C55 C54 C53 110.1(12) . . ?
C55 C54 H54A 109.6 . . ?
C53 C54 H54A 109.6 . . ?
C55 C54 H54B 109.6 . . ?
C53 C54 H54B 109.6 . . ?
H54A C54 H54B 108.2 . . ?
C50 C51 C56 113.2(9) . . ?
C50 C51 C52 109.7(9) . . ?
C56 C51 C52 108.8(9) . . ?
C50 C51 H51 108.4 . . ?
C56 C51 H51 108.4 . . ?
C52 C51 H51 108.4 . . ?
C51 C56 C55 113.1(11) . . ?
C51 C56 H56A 109.0 . . ?
C55 C56 H56A 109.0 . . ?
C51 C56 H56B 109.0 . . ?
C55 C56 H56B 109.0 . . ?
H56A C56 H56B 107.8 . . ?
C54 C55 C56 110.1(11) . . ?
C54 C55 H55A 109.6 . . ?
C56 C55 H55A 109.6 . . ?
C54 C55 H55B 109.6 . . ?
C56 C55 H55B 109.6 . . ?
H55A C55 H55B 108.1 . . ?
C34 N1 H1A 109.5 . . ?
C34 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C34 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C35 C36 C37 112.8(11) . . ?
C35 C36 H36A 109.0 . . ?
C37 C36 H36A 109.0 . . ?
C35 C36 H36B 109.0 . . ?
C37 C36 H36B 109.0 . . ?
H36A C36 H36B 107.8 . . ?
C36 C35 C34 110.1(9) . . ?
C36 C35 C40 109.4(9) . . ?
C34 C35 C40 112.5(8) . . ?
C36 C35 H35 108.2 . . ?
C34 C35 H35 108.2 . . ?
C40 C35 H35 108.2 . . ?
C34 C33 H33A 109.5 . . ?
C34 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C34 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N1 C34 C33 108.5(8) . . ?
N1 C34 C35 111.2(8) . . ?
C33 C34 C35 112.3(8) . . ?
N1 C34 H34 108.2 . . ?
C33 C34 H34 108.2 . . ?
C35 C34 H34 108.2 . . ?
C39 C40 C35 111.5(9) . . ?
C39 C40 H40A 109.3 . . ?
C35 C40 H40A 109.3 . . ?
C39 C40 H40B 109.3 . . ?
C35 C40 H40B 109.3 . . ?
H40A C40 H40B 108.0 . . ?
C38 C37 C36 109.9(11) . . ?
C38 C37 H37A 109.7 . . ?
C36 C37 H37A 109.7 . . ?
C38 C37 H37B 109.7 . . ?
C36 C37 H37B 109.7 . . ?
H37A C37 H37B 108.2 . . ?
C39 C38 C37 111.0(12) . . ?
C39 C38 H38A 109.4 . . ?
C37 C38 H38A 109.4 . . ?
C39 C38 H38B 109.4 . . ?
C37 C38 H38B 109.4 . . ?
H38A C38 H38B 108.0 . . ?
C38 C39 C40 111.7(11) . . ?
C38 C39 H39A 109.3 . . ?
C40 C39 H39A 109.3 . . ?
C38 C39 H39B 109.3 . . ?
C40 C39 H39B 109.3 . . ?
H39A C39 H39B 107.9 . . ?
C58 N4 H4A 109.5 . . ?
C58 N4 H4B 109.5 . . ?
H4A N4 H4B 109.5 . . ?
C58 N4 H4C 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C58 C57 H57A 109.5 . . ?
C58 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C58 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C59' C58 C57 120.7(11) . . ?
C59' C58 N4 112.7(10) . . ?
C57 C58 N4 106.1(8) . . ?
C57 C58 C59 105.4(14) . . ?
N4 C58 C59 106.6(13) . . ?
C59' C58 H58 105.3 . . ?
C57 C58 H58 105.3 . . ?
N4 C58 H58 105.3 . . ?
C58 C59' C60' 115.9(16) . . ?
C58 C59' C64' 108.3(14) . . ?
C60' C59' C64' 110.4(17) . . ?
C58 C59' H59' 107.3 . . ?
C60' C59' H59' 107.3 . . ?
C64' C59' H59' 107.3 . . ?
C61' C60' C59' 114.3(16) . . ?
C61' C60' H60C 108.7 . . ?
C59' C60' H60C 108.7 . . ?
C61' C60' H60D 108.7 . . ?
C59' C60' H60D 108.7 . . ?
H60C C60' H60D 107.6 . . ?
C60' C61' C62' 110.2(17) . . ?
C60' C61' H61C 109.6 . . ?
C62' C61' H61C 109.6 . . ?
C60' C61' H61D 109.6 . . ?
C62' C61' H61D 109.6 . . ?
H61C C61' H61D 108.1 . . ?
C61' C62' C63' 109.5(16) . . ?
C61' C62' H62C 109.8 . . ?
C63' C62' H62C 109.8 . . ?
C61' C62' H62D 109.8 . . ?
C63' C62' H62D 109.8 . . ?
H62C C62' H62D 108.2 . . ?
C64' C63' C62' 112.5(16) . . ?
C64' C63' H63C 109.1 . . ?
C62' C63' H63C 109.1 . . ?
C64' C63' H63D 109.1 . . ?
C62' C63' H63D 109.1 . . ?
H63C C63' H63D 107.8 . . ?
C63' C64' C59' 112.5(15) . . ?
C63' C64' H64C 109.1 . . ?
C59' C64' H64C 109.1 . . ?
C63' C64' H64D 109.1 . . ?
C59' C64' H64D 109.1 . . ?
H64C C64' H64D 107.8 . . ?
C64 C59 C60 110(3) . . ?
C64 C59 C58 109(2) . . ?
C60 C59 C58 112(2) . . ?
C64 C59 H59 108.5 . . ?
C60 C59 H59 108.5 . . ?
C58 C59 H59 108.5 . . ?
C59 C60 C61 111(3) . . ?
C59 C60 H60A 109.4 . . ?
C61 C60 H60A 109.4 . . ?
C59 C60 H60B 109.4 . . ?
C61 C60 H60B 109.4 . . ?
H60A C60 H60B 108.0 . . ?
C62 C61 C60 113(2) . . ?
C62 C61 H61A 108.9 . . ?
C60 C61 H61A 108.9 . . ?
C62 C61 H61B 108.9 . . ?
C60 C61 H61B 108.9 . . ?
H61A C61 H61B 107.7 . . ?
C61 C62 C63 109(2) . . ?
C61 C62 H62A 109.9 . . ?
C63 C62 H62A 109.9 . . ?
C61 C62 H62B 109.9 . . ?
C63 C62 H62B 109.9 . . ?
H62A C62 H62B 108.3 . . ?
C64 C63 C62 113(2) . . ?
C64 C63 H63A 109.0 . . ?
C62 C63 H63A 109.0 . . ?
C64 C63 H63B 109.0 . . ?
C62 C63 H63B 109.0 . . ?
H63A C63 H63B 107.8 . . ?
C63 C64 C59 115(3) . . ?
C63 C64 H64A 108.6 . . ?
C59 C64 H64A 108.6 . . ?
C63 C64 H64B 108.6 . . ?
C59 C64 H64B 108.6 . . ?
H64A C64 H64B 107.6 . . ?
C28 C27 C32 120.0 . . ?
C28 C27 C26 118.2(13) . . ?
C32 C27 C26 121.7(13) . . ?
C27 C28 C29 120.0 . . ?
C27 C28 Cl4 124.6(13) . . ?
C29 C28 Cl4 115.4(13) . . ?
C28 C29 C30 120.0 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 H29 120.0 . . ?
C31 C30 C29 120.0 . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C32 120.0 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C31 C32 C27 120.0 . . ?
C31 C32 H32 120.0 . . ?
C27 C32 H32 120.0 . . ?
C28' C27' C32' 120.0 . . ?
C28' C27' C26 124.1(15) . . ?
C32' C27' C26 115.9(15) . . ?
C29' C28' C27' 120.0 . . ?
C29' C28' Cl4' 118.9(14) . . ?
C27' C28' Cl4' 120.5(14) . . ?
C30' C29' C28' 120.0 . . ?
C30' C29' H29' 120.0 . . ?
C28' C29' H29' 120.0 . . ?
C29' C30' C31' 120.0 . . ?
C29' C30' H30' 120.0 . . ?
C31' C30' H30' 120.0 . . ?
C32' C31' C30' 120.0 . . ?
C32' C31' H31' 120.0 . . ?
C30' C31' H31' 120.0 . . ?
C31' C32' C27' 120.0 . . ?
C31' C32' H32' 120.0 . . ?
C27' C32' H32' 120.0 . . ?
C12' C11' C16' 120.0 . . ?
C12' C11' C10 118.4(10) . . ?
C16' C11' C10 121.5(10) . . ?
C13' C12' C11' 120.0 . . ?
C13' C12' Cl2 115.7(9) . . ?
C11' C12' Cl2 124.3(9) . . ?
C12' C13' C14' 120.0 . . ?
C12' C13' H13' 120.0 . . ?
C14' C13' H13' 120.0 . . ?
C15' C14' C13' 120.0 . . ?
C15' C14' H14' 120.0 . . ?
C13' C14' H14' 120.0 . . ?
C14' C15' C16' 120.0 . . ?
C14' C15' H15' 120.0 . . ?
C16' C15' H15' 120.0 . . ?
C15' C16' C11' 120.0 . . ?
C15' C16' H16' 120.0 . . ?
C11' C16' H16' 120.0 . . ?
C12 C11 C16 120.0 . . ?
C12 C11 C10 126.3(18) . . ?
C16 C11 C10 113.7(18) . . ?
C11 C12 C13 120.0 . . ?
C11 C12 Cl2' 119.9(18) . . ?
C13 C12 Cl2' 120.1(18) . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.0 . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 120.0 . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C20 C19 C24 120.0 . . ?
C20 C19 C18 126.0(12) . . ?
C24 C19 C18 113.6(12) . . ?
C19 C20 C21 120.0 . . ?
C19 C20 Cl3 119.3(10) . . ?
C21 C20 Cl3 120.7(10) . . ?
C22 C21 C20 120.0 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.0 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 120.0 . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C23 C24 C19 120.0 . . ?
C23 C24 H24 120.0 . . ?
C19 C24 H24 120.0 . . ?
C20' C19' C24' 120.0 . . ?
C20' C19' C18 112.1(16) . . ?
C24' C19' C18 127.8(16) . . ?
C21' C20' C19' 120.0 . . ?
C21' C20' Cl3' 111.7(15) . . ?
C19' C20' Cl3' 128.3(15) . . ?
C22' C21' C20' 120.0 . . ?
C22' C21' H21' 120.0 . . ?
C20' C21' H21' 120.0 . . ?
C21' C22' C23' 120.0 . . ?
C21' C22' H22' 120.0 . . ?
C23' C22' H22' 120.0 . . ?
C24' C23' C22' 120.0 . . ?
C24' C23' H23' 120.0 . . ?
C22' C23' H23' 120.0 . . ?
C23' C24' C19' 120.0 . . ?
C23' C24' H24' 120.0 . . ?
C19' C24' H24' 120.0 . . ?
C44 C43 C42 112.1(8) . . ?
C44 C43 C48 110.6(9) . . ?
C42 C43 C48 110.3(10) . . ?
C44 C43 H43 107.9 . . ?
C42 C43 H43 107.9 . . ?
C48 C43 H43 107.9 . . ?
C43 C44 C45' 124.3(17) . . ?
C43 C44 C45 102(2) . . ?
C43 C44 H44A 106.3 . . ?
C45' C44 H44A 106.3 . . ?
C43 C44 H44B 106.3 . . ?
C45' C44 H44B 106.3 . . ?
H44A C44 H44B 106.4 . . ?
C46' C45' C44 106(2) . . ?
C46' C45' H45A 110.4 . . ?
C44 C45' H45A 110.4 . . ?
C46' C45' H45B 110.4 . . ?
C44 C45' H45B 110.4 . . ?
H45A C45' H45B 108.6 . . ?
C45' C46' C47' 111(2) . . ?
C45' C46' H46A 109.5 . . ?
C47' C46' H46A 109.5 . . ?
C45' C46' H46B 109.5 . . ?
C47' C46' H46B 109.5 . . ?
H46A C46' H46B 108.1 . . ?
C46' C47' C48 113(2) . . ?
C46' C47' H47A 108.9 . . ?
C48 C47' H47A 108.9 . . ?
C46' C47' H47B 108.9 . . ?
C48 C47' H47B 108.9 . . ?
H47A C47' H47B 107.7 . . ?
C46 C45 C44 116(2) . . ?
C46 C45 H45C 108.3 . . ?
C44 C45 H45C 108.3 . . ?
C46 C45 H45D 108.3 . . ?
C44 C45 H45D 108.3 . . ?
H45C C45 H45D 107.4 . . ?
C45 C46 C47 111(2) . . ?
C45 C46 H46C 109.5 . . ?
C47 C46 H46C 109.5 . . ?
C45 C46 H46D 109.5 . . ?
C47 C46 H46D 109.5 . . ?
H46C C46 H46D 108.0 . . ?
C48 C47 C46 104.7(19) . . ?
C48 C47 H47C 110.8 . . ?
C46 C47 H47C 110.8 . . ?
C48 C47 H47D 110.8 . . ?
C46 C47 H47D 110.8 . . ?
H47C C47 H47D 108.9 . . ?
C47 C48 C43 123(2) . . ?
C43 C48 C47' 104.1(14) . . ?
C43 C48 H48A 110.9 . . ?
C47' C48 H48A 110.9 . . ?
C43 C48 H48B 110.9 . . ?
C47' C48 H48B 110.9 . . ?
H48A C48 H48B 109.0 . . ?

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
O10 C17 C18 O12 -23.6(14) . . . . ?
O11 C17 C18 O12 159.7(9) . . . . ?
O10 C17 C18 C19' 97.6(13) . . . . ?
O11 C17 C18 C19' -79.1(14) . . . . ?
O10 C17 C18 C19 97.3(12) . . . . ?
O11 C17 C18 C19 -79.4(13) . . . . ?
C6 C5 C4 C3 2.1(16) . . . . ?
C6 C5 C4 Cl1 -179.2(8) . . . . ?
C4 C5 C6 C7 -1.4(17) . . . . ?
C5 C4 C3 C8 -1.7(14) . . . . ?
Cl1 C4 C3 C8 179.7(7) . . . . ?
C5 C4 C3 C2 175.0(9) . . . . ?
Cl1 C4 C3 C2 -3.7(13) . . . . ?
C7 C8 C3 C4 0.6(15) . . . . ?
C7 C8 C3 C2 -176.1(10) . . . . ?
C4 C3 C2 O3 -90.3(10) . . . . ?
C8 C3 C2 O3 86.1(10) . . . . ?
C4 C3 C2 C1 146.9(9) . . . . ?
C8 C3 C2 C1 -36.7(12) . . . . ?
O1 C1 C2 O3 -22.6(14) . . . . ?
O2 C1 C2 O3 157.2(9) . . . . ?
O1 C1 C2 C3 97.6(11) . . . . ?
O2 C1 C2 C3 -82.6(11) . . . . ?
C3 C8 C7 C6 -0.1(17) . . . . ?
C5 C6 C7 C8 0.5(17) . . . . ?
O5 C9 C10 O6 154.9(9) . . . . ?
O4 C9 C10 O6 -27.6(13) . . . . ?
O5 C9 C10 C11' -89.9(13) . . . . ?
O4 C9 C10 C11' 87.6(13) . . . . ?
O5 C9 C10 C11 -74.0(17) . . . . ?
O4 C9 C10 C11 103.5(16) . . . . ?
O7 C25 C26 O9 -35.5(13) . . . . ?
O8 C25 C26 O9 146.2(9) . . . . ?
O7 C25 C26 C27' 94.1(14) . . . . ?
O8 C25 C26 C27' -84.1(14) . . . . ?
O7 C25 C26 C27 78.1(14) . . . . ?
O8 C25 C26 C27 -100.1(13) . . . . ?
C51 C52 C53 C54 -56.0(15) . . . . ?
C52 C53 C54 C55 56.8(17) . . . . ?
N3 C50 C51 C56 -52.2(12) . . . . ?
C49 C50 C51 C56 -174.9(10) . . . . ?
N3 C50 C51 C52 -173.9(9) . . . . ?
C49 C50 C51 C52 63.4(12) . . . . ?
C53 C52 C51 C50 178.4(11) . . . . ?
C53 C52 C51 C56 54.1(14) . . . . ?
C50 C51 C56 C55 -177.4(10) . . . . ?
C52 C51 C56 C55 -55.2(14) . . . . ?
C53 C54 C55 C56 -56.1(18) . . . . ?
C51 C56 C55 C54 57.7(17) . . . . ?
C37 C36 C35 C34 179.0(11) . . . . ?
C37 C36 C35 C40 54.9(14) . . . . ?
C36 C35 C34 N1 -170.6(9) . . . . ?
C40 C35 C34 N1 -48.3(12) . . . . ?
C36 C35 C34 C33 67.6(12) . . . . ?
C40 C35 C34 C33 -170.1(9) . . . . ?
C36 C35 C40 C39 -54.2(13) . . . . ?
C34 C35 C40 C39 -176.9(10) . . . . ?
C35 C36 C37 C38 -56.4(17) . . . . ?
C36 C37 C38 C39 56.3(18) . . . . ?
C37 C38 C39 C40 -57.4(17) . . . . ?
C35 C40 C39 C38 56.4(15) . . . . ?
C57 C58 C59' C60' -176.1(14) . . . . ?
N4 C58 C59' C60' -49(2) . . . . ?
C57 C58 C59' C64' 59(2) . . . . ?
N4 C58 C59' C64' -173.9(14) . . . . ?
C58 C59' C60' C61' -175.5(18) . . . . ?
C64' C59' C60' C61' -52(3) . . . . ?
C59' C60' C61' C62' 58(2) . . . . ?
C60' C61' C62' C63' -58(2) . . . . ?
C61' C62' C63' C64' 57(2) . . . . ?
C62' C63' C64' C59' -53(3) . . . . ?
C58 C59' C64' C63' 176.5(18) . . . . ?
C60' C59' C64' C63' 49(3) . . . . ?
C57 C58 C59 C64 67(2) . . . . ?
N4 C58 C59 C64 179.6(19) . . . . ?
C57 C58 C59 C60 -171(2) . . . . ?
N4 C58 C59 C60 -58(3) . . . . ?
C64 C59 C60 C61 53(4) . . . . ?
C58 C59 C60 C61 -69(3) . . . . ?
C59 C60 C61 C62 -56(4) . . . . ?
C60 C61 C62 C63 54(3) . . . . ?
C61 C62 C63 C64 -53(3) . . . . ?
C62 C63 C64 C59 54(4) . . . . ?
C60 C59 C64 C63 -53(4) . . . . ?
C58 C59 C64 C63 71(3) . . . . ?
O9 C26 C27 C28 -138.3(11) . . . . ?
C25 C26 C27 C28 103.3(13) . . . . ?
O9 C26 C27 C32 44.5(16) . . . . ?
C25 C26 C27 C32 -73.9(16) . . . . ?
C32 C27 C28 C29 0.0 . . . . ?
C26 C27 C28 C29 -177.2(19) . . . . ?
C32 C27 C28 Cl4 -177.6(19) . . . . ?
C26 C27 C28 Cl4 5.3(17) . . . . ?
C27 C28 C29 C30 0.0 . . . . ?
Cl4 C28 C29 C30 177.8(17) . . . . ?
C28 C29 C30 C31 0.0 . . . . ?
C29 C30 C31 C32 0.0 . . . . ?
C30 C31 C32 C27 0.0 . . . . ?
C28 C27 C32 C31 0.0 . . . . ?
C26 C27 C32 C31 177(2) . . . . ?
O9 C26 C27' C28' -129.3(14) . . . . ?
C25 C26 C27' C28' 103.8(15) . . . . ?
O9 C26 C27' C32' 50.8(16) . . . . ?
C25 C26 C27' C32' -76.0(15) . . . . ?
C32' C27' C28' C29' 0.0 . . . . ?
C26 C27' C28' C29' -180(2) . . . . ?
C32' C27' C28' Cl4' -171.5(19) . . . . ?
C26 C27' C28' Cl4' 9(2) . . . . ?
C27' C28' C29' C30' 0.0 . . . . ?
Cl4' C28' C29' C30' 171.7(19) . . . . ?
C28' C29' C30' C31' 0.0 . . . . ?
C29' C30' C31' C32' 0.0 . . . . ?
C30' C31' C32' C27' 0.0 . . . . ?
C28' C27' C32' C31' 0.0 . . . . ?
C26 C27' C32' C31' 179.9(19) . . . . ?
O6 C10 C11' C12' -133.2(9) . . . . ?
C9 C10 C11' C12' 106.4(11) . . . . ?
O6 C10 C11' C16' 48.5(12) . . . . ?
C9 C10 C11' C16' -71.8(13) . . . . ?
C16' C11' C12' C13' 0.0 . . . . ?
C10 C11' C12' C13' -178.2(14) . . . . ?
C16' C11' C12' Cl2 -179.2(13) . . . . ?
C10 C11' C12' Cl2 2.6(14) . . . . ?
C11' C12' C13' C14' 0.0 . . . . ?
Cl2 C12' C13' C14' 179.3(12) . . . . ?
C12' C13' C14' C15' 0.0 . . . . ?
C13' C14' C15' C16' 0.0 . . . . ?
C14' C15' C16' C11' 0.0 . . . . ?
C12' C11' C16' C15' 0.0 . . . . ?
C10 C11' C16' C15' 178.2(14) . . . . ?
O6 C10 C11 C12 -133(2) . . . . ?
C9 C10 C11 C12 98(2) . . . . ?
O6 C10 C11 C16 46(2) . . . . ?
C9 C10 C11 C16 -82(2) . . . . ?
C16 C11 C12 C13 0.0 . . . . ?
C10 C11 C12 C13 180(3) . . . . ?
C16 C11 C12 Cl2' 179(3) . . . . ?
C10 C11 C12 Cl2' -2(3) . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
Cl2' C12 C13 C14 -179(3) . . . . ?
C12 C13 C14 C15 0.0 . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C14 C15 C16 C11 0.0 . . . . ?
C12 C11 C16 C15 0.0 . . . . ?
C10 C11 C16 C15 -180(2) . . . . ?
O12 C18 C19 C20 -125.6(13) . . . . ?
C17 C18 C19 C20 112.4(15) . . . . ?
O12 C18 C19 C24 61.3(12) . . . . ?
C17 C18 C19 C24 -60.6(13) . . . . ?
C24 C19 C20 C21 0.0 . . . . ?
C18 C19 C20 C21 -172.6(17) . . . . ?
C24 C19 C20 Cl3 179.2(13) . . . . ?
C18 C19 C20 Cl3 6.6(14) . . . . ?
C19 C20 C21 C22 0.0 . . . . ?
Cl3 C20 C21 C22 -179.2(14) . . . . ?
C20 C21 C22 C23 0.0 . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C22 C23 C24 C19 0.0 . . . . ?
C20 C19 C24 C23 0.0 . . . . ?
C18 C19 C24 C23 173.5(15) . . . . ?
O12 C18 C19' C20' -101.2(17) . . . . ?
C17 C18 C19' C20' 137.9(16) . . . . ?
O12 C18 C19' C24' 75(2) . . . . ?
C17 C18 C19' C24' -46(2) . . . . ?
C24' C19' C20' C21' 0.0 . . . . ?
C18 C19' C20' C21' 176.6(19) . . . . ?
C24' C19' C20' Cl3' 177(3) . . . . ?
C18 C19' C20' Cl3' -6(2) . . . . ?
C19' C20' C21' C22' 0.0 . . . . ?
Cl3' C20' C21' C22' -178(2) . . . . ?
C20' C21' C22' C23' 0.0 . . . . ?
C21' C22' C23' C24' 0.0 . . . . ?
C22' C23' C24' C19' 0.0 . . . . ?
C20' C19' C24' C23' 0.0 . . . . ?
C18 C19' C24' C23' -176(2) . . . . ?
N2 C42 C43 C44 -49.8(11) . . . . ?
C41 C42 C43 C44 -173.5(10) . . . . ?
N2 C42 C43 C48 -173.4(8) . . . . ?
C41 C42 C43 C48 62.8(12) . . . . ?
C42 C43 C44 C45' -173.0(15) . . . . ?
C48 C43 C44 C45' -49.5(19) . . . . ?
C42 C43 C44 C45 -175.4(14) . . . . ?
C48 C43 C44 C45 -52.0(16) . . . . ?
C43 C44 C45' C46' 48(3) . . . . ?
C44 C45' C46' C47' -52(3) . . . . ?
C45' C46' C47' C48 65(3) . . . . ?
C43 C44 C45 C46 64(3) . . . . ?
C44 C45 C46 C47 -64(4) . . . . ?
C45 C46 C47 C48 48(4) . . . . ?
C46 C47 C48 C43 -47(4) . . . . ?
C44 C43 C48 C47 54(2) . . . . ?
C42 C43 C48 C47 178(2) . . . . ?
C44 C43 C48 C47' 48.3(15) . . . . ?
C42 C43 C48 C47' 172.8(12) . . . . ?
C46' C47' C48 C43 -61(2) . . . . ?

_refine_diff_density_max         0.481
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.052



