# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
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# Crystallographic Data Centre (CCDC).
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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data_mo_dakl365_p21n
_database_code_depnum_ccdc_archive 'CCDC 1540803'
_audit_update_record             
;
2017-03-29 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;
_audit_creation_date             2017-03-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelxl_version_number           2013-2
_chemical_name_systematic        
;3-(2-(5-chloro-2-ethoxy-3-(isopropylthio)phenyl)-2-cyclohexylacetyl)
oxazolidin-2-one
;
_chemical_name_common            ?
_chemical_formula_moiety         'C22 H30 Cl N O4 S'
_chemical_formula_sum            'C22 H30 Cl N O4 S'
_chemical_formula_weight         439.98
_chemical_melting_point          ?
_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colourless'
_diffrn_ambient_temperature      100.0
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.0663(6)
_cell_length_b                   10.1526(5)
_cell_length_c                   18.2867(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.196(2)
_cell_angle_gamma                90
_cell_volume                     2181.05(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9592
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.025
_cell_measurement_theta_min      2.285
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.755
_exptl_absorpt_coefficient_mu    0.299
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.3209
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction. 
wR2(int) was 0.1532 before and 0.0625 after correction. 
The Ratio of minimum to maximum transmission is 0.4302. 
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             936
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.995
_exptl_crystal_size_mid          0.558
_exptl_crystal_size_min          0.186
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1162
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            63457
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.083
_diffrn_reflns_theta_min         2.285
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed  X-ray tube'
_diffrn_source_type              'Incoatec IuSMo'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5250
_reflns_number_total             6407
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'APEX2 v2013.6-2'
_computing_data_collection       'APEX2 v2013.6-2'
_computing_data_reduction        'APEX2 v2013.6-2'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         6407
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0396P)²+0.7640P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0945
_refine_special_details          
;
_olex2_refinement_description
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C6(H6), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,
 H10B), C11(H11A,H11B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C17(H17)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.84451(2) 0.86629(3) 0.56336(2) 0.01960(8) Uani 1 1 d . . . . .
S1 S 0.47935(2) 0.69820(3) 0.34450(2) 0.01620(8) Uani 1 1 d . . . . .
O1 O 0.71870(8) 0.05625(9) 0.30546(5) 0.0216(2) Uani 1 1 d . . . . .
O2 O 0.90597(7) 0.42341(8) 0.38465(5) 0.01676(18) Uani 1 1 d . . . . .
O3 O 0.67717(8) 0.12185(8) 0.41276(5) 0.01951(19) Uani 1 1 d . . . . .
O4 O 0.58366(6) 0.44733(8) 0.38116(5) 0.01223(16) Uani 1 1 d . . . . .
N1 N 0.79766(8) 0.24440(9) 0.35455(6) 0.01369(19) Uani 1 1 d . . . . .
C1 C 0.79312(9) 0.37310(10) 0.47318(6) 0.0107(2) Uani 1 1 d . . . . .
H1 H 0.7273 0.3130 0.4726 0.013 Uiso 1 1 calc R . . . .
C2 C 0.83605(9) 0.35060(11) 0.40198(7) 0.0118(2) Uani 1 1 d . . . . .
C3 C 0.72597(10) 0.14044(11) 0.36355(7) 0.0151(2) Uani 1 1 d . . . . .
C4 C 0.77872(11) 0.10704(13) 0.25120(8) 0.0214(3) Uani 1 1 d . . . . .
H4A H 0.7243 0.1352 0.2048 0.026 Uiso 1 1 calc R . . . .
H4B H 0.8297 0.0390 0.2381 0.026 Uiso 1 1 calc R . . . .
C5 C 0.84709(11) 0.22379(13) 0.28933(7) 0.0197(3) Uani 1 1 d . . . . .
H5A H 0.9292 0.2026 0.3048 0.024 Uiso 1 1 calc R . . . .
H5B H 0.8366 0.3021 0.2562 0.024 Uiso 1 1 calc R . . . .
C6 C 0.88968(9) 0.33963(10) 0.54189(6) 0.0112(2) Uani 1 1 d . . . . .
H6 H 0.9545 0.4015 0.5428 0.013 Uiso 1 1 calc R . . . .
C7 C 0.85021(10) 0.35545(11) 0.61519(7) 0.0153(2) Uani 1 1 d . . . . .
H7A H 0.8254 0.4475 0.6197 0.018 Uiso 1 1 calc R . . . .
H7B H 0.7842 0.2971 0.6142 0.018 Uiso 1 1 calc R . . . .
C8 C 0.94553(12) 0.32137(13) 0.68310(7) 0.0209(3) Uani 1 1 d . . . . .
H8A H 1.0090 0.3845 0.6863 0.025 Uiso 1 1 calc R . . . .
H8B H 0.9169 0.3300 0.7295 0.025 Uiso 1 1 calc R . . . .
C9 C 0.98942(12) 0.18144(13) 0.67782(8) 0.0240(3) Uani 1 1 d . . . . .
H9A H 1.0545 0.1646 0.7207 0.029 Uiso 1 1 calc R . . . .
H9B H 0.9285 0.1175 0.6806 0.029 Uiso 1 1 calc R . . . .
C10 C 1.02697(11) 0.16233(12) 0.60442(8) 0.0200(3) Uani 1 1 d . . . . .
H10A H 1.0494 0.0693 0.6002 0.024 Uiso 1 1 calc R . . . .
H10B H 1.0944 0.2182 0.6047 0.024 Uiso 1 1 calc R . . . .
C11 C 0.93203(10) 0.19810(11) 0.53643(7) 0.0154(2) Uani 1 1 d . . . . .
H11A H 0.8677 0.1362 0.5331 0.018 Uiso 1 1 calc R . . . .
H11B H 0.9606 0.1889 0.4901 0.018 Uiso 1 1 calc R . . . .
C12 C 0.75191(9) 0.51520(10) 0.47068(6) 0.0108(2) Uani 1 1 d . . . . .
C13 C 0.64759(9) 0.54637(11) 0.42293(6) 0.0110(2) Uani 1 1 d . . . . .
C14 C 0.60753(9) 0.67673(11) 0.41225(7) 0.0123(2) Uani 1 1 d . . . . .
C15 C 0.67130(9) 0.77729(11) 0.45434(7) 0.0136(2) Uani 1 1 d . . . . .
H15 H 0.6467 0.8663 0.4485 0.016 Uiso 1 1 calc R . . . .
C16 C 0.77172(9) 0.74322(11) 0.50496(7) 0.0131(2) Uani 1 1 d . . . . .
C17 C 0.81488(9) 0.61669(11) 0.51233(7) 0.0124(2) Uani 1 1 d . . . . .
H17 H 0.8864 0.5989 0.5453 0.015 Uiso 1 1 calc R . . . .
C18 C 0.49782(9) 0.39591(11) 0.41808(7) 0.0140(2) Uani 1 1 d . . . . .
H18A H 0.4504 0.4687 0.4303 0.017 Uiso 1 1 calc R . . . .
H18B H 0.5347 0.3507 0.4653 0.017 Uiso 1 1 calc R . . . .
C19 C 0.42541(11) 0.30069(13) 0.36499(8) 0.0210(3) Uani 1 1 d . . . . .
H19A H 0.3649 0.2668 0.3876 0.032 Uiso 1 1 calc GR . . . .
H19B H 0.4726 0.2274 0.3549 0.032 Uiso 1 1 calc GR . . . .
H19C H 0.3915 0.3458 0.3178 0.032 Uiso 1 1 calc GR . . . .
C20 C 0.44760(10) 0.87350(12) 0.34777(8) 0.0205(3) Uani 1 1 d . . . . .
H20 H 0.5163 0.9259 0.3441 0.025 Uiso 1 1 calc R . . . .
C21 C 0.41006(11) 0.91218(13) 0.41879(9) 0.0255(3) Uani 1 1 d . . . . .
H21A H 0.3378 0.8687 0.4194 0.038 Uiso 1 1 calc GR . . . .
H21B H 0.4001 1.0079 0.4198 0.038 Uiso 1 1 calc GR . . . .
H21C H 0.4681 0.8849 0.4629 0.038 Uiso 1 1 calc GR . . . .
C22 C 0.35310(13) 0.89673(15) 0.27766(10) 0.0349(4) Uani 1 1 d . . . . .
H22A H 0.3823 0.8797 0.2328 0.052 Uiso 1 1 calc GR . . . .
H22B H 0.3270 0.9882 0.2770 0.052 Uiso 1 1 calc GR . . . .
H22C H 0.2893 0.8372 0.2782 0.052 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C16 1.7448(11) . ?
S1 C14 1.7607(11) . ?
S1 C20 1.8243(13) . ?
O1 C3 1.3507(15) . ?
O1 C4 1.4500(16) . ?
O2 C2 1.2168(14) . ?
O3 C3 1.1976(15) . ?
O4 C13 1.3858(13) . ?
O4 C18 1.4561(13) . ?
N1 C2 1.3949(14) . ?
N1 C3 1.3979(15) . ?
N1 C5 1.4652(16) . ?
C1 C2 1.5245(16) . ?
C1 C6 1.5438(15) . ?
C1 C12 1.5233(14) . ?
C4 C5 1.5196(17) . ?
C6 C7 1.5299(17) . ?
C6 C11 1.5359(15) . ?
C7 C8 1.5274(17) . ?
C8 C9 1.5269(18) . ?
C9 C10 1.5239(19) . ?
C10 C11 1.5296(17) . ?
C12 C13 1.3947(15) . ?
C12 C17 1.3982(15) . ?
C13 C14 1.4073(15) . ?
C14 C15 1.3987(16) . ?
C15 C16 1.3902(16) . ?
C16 C17 1.3811(15) . ?
C18 C19 1.5012(16) . ?
C20 C21 1.521(2) . ?
C20 C22 1.5271(19) . ?

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
C14 S1 C20 104.78(6) . . ?
C3 O1 C4 111.11(9) . . ?
C13 O4 C18 111.71(8) . . ?
C2 N1 C3 129.57(10) . . ?
C2 N1 C5 118.52(9) . . ?
C3 N1 C5 111.45(10) . . ?
C2 C1 C6 108.77(9) . . ?
C12 C1 C2 106.77(9) . . ?
C12 C1 C6 114.43(9) . . ?
O2 C2 N1 117.34(11) . . ?
O2 C2 C1 121.49(10) . . ?
N1 C2 C1 121.17(9) . . ?
O1 C3 N1 108.42(10) . . ?
O3 C3 O1 122.44(11) . . ?
O3 C3 N1 129.13(11) . . ?
O1 C4 C5 105.49(10) . . ?
N1 C5 C4 101.87(10) . . ?
C7 C6 C1 111.21(9) . . ?
C7 C6 C11 109.26(9) . . ?
C11 C6 C1 110.70(9) . . ?
C8 C7 C6 111.19(10) . . ?
C9 C8 C7 111.53(11) . . ?
C10 C9 C8 110.57(11) . . ?
C9 C10 C11 111.57(10) . . ?
C10 C11 C6 111.58(10) . . ?
C13 C12 C1 118.39(9) . . ?
C13 C12 C17 118.32(10) . . ?
C17 C12 C1 123.26(10) . . ?
O4 C13 C12 119.32(9) . . ?
O4 C13 C14 118.39(10) . . ?
C12 C13 C14 122.18(10) . . ?
C13 C14 S1 115.65(8) . . ?
C15 C14 S1 125.55(9) . . ?
C15 C14 C13 118.80(10) . . ?
C16 C15 C14 118.11(10) . . ?
C15 C16 Cl1 118.02(8) . . ?
C17 C16 Cl1 118.71(9) . . ?
C17 C16 C15 123.25(10) . . ?
C16 C17 C12 119.10(10) . . ?
O4 C18 C19 107.56(9) . . ?
C21 C20 S1 112.67(9) . . ?
C21 C20 C22 111.47(12) . . ?
C22 C20 S1 104.20(10) . . ?

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
Cl1 C16 C17 C12 174.23(9) . . . . ?
S1 C14 C15 C16 -179.16(9) . . . . ?
O1 C4 C5 N1 -12.49(13) . . . . ?
O4 C13 C14 S1 -0.97(14) . . . . ?
O4 C13 C14 C15 179.79(10) . . . . ?
C1 C6 C7 C8 179.59(9) . . . . ?
C1 C6 C11 C10 -179.40(10) . . . . ?
C1 C12 C13 O4 1.79(15) . . . . ?
C1 C12 C13 C14 -174.47(10) . . . . ?
C1 C12 C17 C16 178.40(10) . . . . ?
C2 N1 C3 O1 -175.97(11) . . . . ?
C2 N1 C3 O3 3.5(2) . . . . ?
C2 N1 C5 C4 -176.67(10) . . . . ?
C2 C1 C6 C7 -177.89(9) . . . . ?
C2 C1 C6 C11 -56.23(11) . . . . ?
C2 C1 C12 C13 75.99(12) . . . . ?
C2 C1 C12 C17 -102.20(12) . . . . ?
C3 O1 C4 C5 11.26(13) . . . . ?
C3 N1 C2 O2 174.14(11) . . . . ?
C3 N1 C2 C1 -5.04(17) . . . . ?
C3 N1 C5 C4 10.40(13) . . . . ?
C4 O1 C3 O3 175.64(11) . . . . ?
C4 O1 C3 N1 -4.82(13) . . . . ?
C5 N1 C2 O2 2.68(16) . . . . ?
C5 N1 C2 C1 -176.49(10) . . . . ?
C5 N1 C3 O1 -4.03(13) . . . . ?
C5 N1 C3 O3 175.46(12) . . . . ?
C6 C1 C2 O2 -71.09(13) . . . . ?
C6 C1 C2 N1 108.06(11) . . . . ?
C6 C1 C12 C13 -163.62(10) . . . . ?
C6 C1 C12 C17 18.19(15) . . . . ?
C6 C7 C8 C9 -57.38(13) . . . . ?
C7 C6 C11 C10 -56.59(12) . . . . ?
C7 C8 C9 C10 55.26(15) . . . . ?
C8 C9 C10 C11 -54.56(15) . . . . ?
C9 C10 C11 C6 56.14(14) . . . . ?
C11 C6 C7 C8 57.09(12) . . . . ?
C12 C1 C2 O2 52.87(13) . . . . ?
C12 C1 C2 N1 -127.99(10) . . . . ?
C12 C1 C6 C7 62.84(12) . . . . ?
C12 C1 C6 C11 -175.50(9) . . . . ?
C12 C13 C14 S1 175.32(9) . . . . ?
C12 C13 C14 C15 -3.92(17) . . . . ?
C13 O4 C18 C19 173.89(9) . . . . ?
C13 C12 C17 C16 0.21(17) . . . . ?
C13 C14 C15 C16 0.00(17) . . . . ?
C14 S1 C20 C21 -71.56(10) . . . . ?
C14 S1 C20 C22 167.44(9) . . . . ?
C14 C15 C16 Cl1 -174.38(9) . . . . ?
C14 C15 C16 C17 4.09(18) . . . . ?
C15 C16 C17 C12 -4.22(18) . . . . ?
C17 C12 C13 O4 -179.93(10) . . . . ?
C17 C12 C13 C14 3.81(17) . . . . ?
C18 O4 C13 C12 95.88(12) . . . . ?
C18 O4 C13 C14 -87.72(12) . . . . ?
C20 S1 C14 C13 177.17(9) . . . . ?
C20 S1 C14 C15 -3.65(12) . . . . ?

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'P 21/n'
_symmetry_int_tables_number      14
_chemical_absolute_configuration .

####################################################################### 
# 
# 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_madr050_fdd2
_database_code_depnum_ccdc_archive 'CCDC 1568395'
_audit_update_record             
;
2017-08-11 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;
_audit_creation_date             2017-08-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelxl_version_number           2013-2
_chemical_name_systematic        
3-(2-phenyl-2-(4-(phenylthio)phenyl)acetyl)oxazolidin-2-one
_chemical_name_common            ?
_chemical_formula_moiety         'C23 H19 N O3 S'
_chemical_formula_sum            'C23 H19 N O3 S'
_chemical_formula_weight         389.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
_chemical_absolute_configuration .
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_diffrn_ambient_temperature      130.0
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   22.362(13)
_cell_length_b                   58.28(3)
_cell_length_c                   5.779(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7532(8)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    1696
_cell_measurement_temperature    130.0
_cell_measurement_theta_max      18.532
_cell_measurement_theta_min      2.296
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction. 
wR2(int) was 0.1330 before and 0.0640 after correction. 
The Ratio of minimum to maximum transmission is 0.7939. 
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             3264
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1260
_diffrn_reflns_av_unetI/netI     0.1131
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       69
_diffrn_reflns_limit_k_min       -67
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            19341
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         2.296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed xray tube'
_diffrn_source_type              'Incoatec IuS'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2253
_reflns_number_total             3404
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.32B (?, 2016)'
_computing_data_collection       'APEX 2 (Bruker, 2011)'
_computing_data_reduction        'SAINT V8.32B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Flack x determined using 725 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.18(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3404
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0627
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0634P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1412
_refine_special_details          
;
_olex2_refinement_description
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.42293(8) 0.02397(3) 0.7859(4) 0.0402(5) Uani 1 1 d . . . . .
O1 O 0.38654(17) -0.10245(8) 0.7863(8) 0.0325(11) Uani 1 1 d . . . . .
O2 O 0.23254(18) -0.08631(8) 1.2416(8) 0.0355(12) Uani 1 1 d . . . . .
O3 O 0.3161(2) -0.06996(9) 1.3766(8) 0.0414(13) Uani 1 1 d . . . . .
N1 N 0.3148(2) -0.09024(8) 1.0279(9) 0.0243(12) Uani 1 1 d . . . . .
C1 C 0.3740(3) -0.09064(11) 0.9558(12) 0.0271(16) Uani 1 1 d . . . . .
C2 C 0.4196(2) -0.07629(11) 1.0827(11) 0.0252(15) Uani 1 1 d . . . . .
H2 H 0.4103 -0.0773 1.2518 0.030 Uiso 1 1 calc R . . . .
C3 C 0.4828(3) -0.08564(10) 1.0468(12) 0.0256(15) Uani 1 1 d . . . . .
C4 C 0.5171(3) -0.07972(12) 0.8583(12) 0.0296(17) Uani 1 1 d . . . . .
H4 H 0.5007 -0.0698 0.7440 0.035 Uiso 1 1 calc R . . . .
C5 C 0.5751(3) -0.08785(12) 0.8311(13) 0.0386(19) Uani 1 1 d . . . . .
H5 H 0.5980 -0.0834 0.7004 0.046 Uiso 1 1 calc R . . . .
C6 C 0.5991(3) -0.10238(12) 0.9935(12) 0.0313(17) Uani 1 1 d . . . . .
H6 H 0.6388 -0.1080 0.9757 0.038 Uiso 1 1 calc R . . . .
C7 C 0.5652(3) -0.10884(14) 1.1837(12) 0.040(2) Uani 1 1 d . . . . .
H7 H 0.5813 -0.1190 1.2961 0.048 Uiso 1 1 calc R . . . .
C8 C 0.5081(3) -0.10044(12) 1.2082(11) 0.0329(18) Uani 1 1 d . . . . .
H8 H 0.4853 -0.1049 1.3395 0.039 Uiso 1 1 calc R . . . .
C9 C 0.2906(3) -0.08085(13) 1.2315(13) 0.0342(18) Uani 1 1 d . . . . .
C10 C 0.2134(3) -0.09856(12) 1.0345(13) 0.0362(17) Uani 1 1 d . . . . .
H10A H 0.1854 -0.0890 0.9428 0.043 Uiso 1 1 calc R . . . .
H10B H 0.1930 -0.1130 1.0769 0.043 Uiso 1 1 calc R . . . .
C11 C 0.2696(3) -0.10347(12) 0.8974(12) 0.0326(17) Uani 1 1 d . . . . .
H11A H 0.2791 -0.1201 0.8966 0.039 Uiso 1 1 calc R . . . .
H11B H 0.2660 -0.0979 0.7360 0.039 Uiso 1 1 calc R . . . .
C12 C 0.4144(2) -0.05136(11) 1.0114(12) 0.0259(15) Uani 1 1 d . . . . .
C13 C 0.4336(3) -0.03382(12) 1.1600(12) 0.0295(17) Uani 1 1 d . . . . .
H13 H 0.4478 -0.0376 1.3100 0.035 Uiso 1 1 calc R . . . .
C14 C 0.4324(3) -0.01123(12) 1.0927(12) 0.0286(16) Uani 1 1 d . . . . .
H14 H 0.4450 0.0003 1.1979 0.034 Uiso 1 1 calc R . . . .
C15 C 0.4128(3) -0.00497(11) 0.8715(12) 0.0283(17) Uani 1 1 d . . . . .
C16 C 0.3925(3) -0.02200(11) 0.7224(11) 0.0281(16) Uani 1 1 d . . . . .
H16 H 0.3785 -0.0181 0.5723 0.034 Uiso 1 1 calc R . . . .
C17 C 0.3927(2) -0.04478(11) 0.7939(12) 0.0276(16) Uani 1 1 d . . . . .
H17 H 0.3777 -0.0562 0.6923 0.033 Uiso 1 1 calc R . . . .
C18 C 0.3609(3) 0.02912(12) 0.5984(12) 0.0327(18) Uani 1 1 d . . . . .
C19 C 0.3723(3) 0.04075(12) 0.3895(12) 0.0346(18) Uani 1 1 d . . . . .
H19 H 0.4120 0.0449 0.3479 0.042 Uiso 1 1 calc R . . . .
C20 C 0.3246(3) 0.04595(12) 0.2455(13) 0.0388(18) Uani 1 1 d . . . . .
H20 H 0.3319 0.0538 0.1042 0.047 Uiso 1 1 calc R . . . .
C21 C 0.2668(3) 0.03999(12) 0.3025(14) 0.0412(19) Uani 1 1 d . . . . .
H21 H 0.2347 0.0436 0.2012 0.049 Uiso 1 1 calc R . . . .
C22 C 0.2561(3) 0.02872(11) 0.5084(13) 0.0353(18) Uani 1 1 d . . . . .
H22 H 0.2164 0.0245 0.5482 0.042 Uiso 1 1 calc R . . . .
C23 C 0.3028(3) 0.02348(12) 0.6579(12) 0.0318(17) Uani 1 1 d . . . . .
H23 H 0.2948 0.0160 0.8008 0.038 Uiso 1 1 calc R . . . .


_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
S1 C15 1.772(7) . ?
S1 C18 1.786(7) . ?
O1 C1 1.230(8) . ?
O2 C9 1.337(7) . ?
O2 C10 1.458(8) . ?
O3 C9 1.197(8) . ?
N1 C1 1.388(8) . ?
N1 C9 1.406(9) . ?
N1 C11 1.478(8) . ?
C1 C2 1.509(9) . ?
C2 C3 1.529(8) . ?
C2 C12 1.515(9) . ?
C3 C4 1.377(8) . ?
C3 C8 1.391(9) . ?
C4 C5 1.389(9) . ?
C5 C6 1.374(9) . ?
C6 C7 1.387(9) . ?
C7 C8 1.374(9) . ?
C10 C11 1.512(9) . ?
C12 C13 1.403(9) . ?
C12 C17 1.400(9) . ?
C13 C14 1.373(9) . ?
C14 C15 1.399(10) . ?
C15 C16 1.391(9) . ?
C16 C17 1.391(9) . ?
C18 C19 1.408(9) . ?
C18 C23 1.383(9) . ?
C19 C20 1.387(9) . ?
C20 C21 1.378(9) . ?
C21 C22 1.380(10) . ?
C22 C23 1.390(9) . ?

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
C15 S1 C18 103.3(3) . . ?
C9 O2 C10 111.4(5) . . ?
C1 N1 C9 128.7(5) . . ?
C1 N1 C11 119.3(5) . . ?
C9 N1 C11 111.5(5) . . ?
O1 C1 N1 117.8(6) . . ?
O1 C1 C2 122.9(6) . . ?
N1 C1 C2 119.3(6) . . ?
C1 C2 C3 111.2(5) . . ?
C1 C2 C12 110.3(5) . . ?
C12 C2 C3 112.1(5) . . ?
C4 C3 C2 122.2(6) . . ?
C4 C3 C8 117.3(6) . . ?
C8 C3 C2 120.5(6) . . ?
C3 C4 C5 121.6(7) . . ?
C6 C5 C4 119.9(7) . . ?
C5 C6 C7 119.6(6) . . ?
C8 C7 C6 119.5(6) . . ?
C7 C8 C3 122.0(6) . . ?
O2 C9 N1 108.5(6) . . ?
O3 C9 O2 123.9(6) . . ?
O3 C9 N1 127.5(6) . . ?
O2 C10 C11 106.2(5) . . ?
N1 C11 C10 101.6(5) . . ?
C13 C12 C2 120.6(6) . . ?
C17 C12 C2 122.2(6) . . ?
C17 C12 C13 117.1(6) . . ?
C14 C13 C12 121.3(6) . . ?
C13 C14 C15 121.0(6) . . ?
C14 C15 S1 117.6(5) . . ?
C16 C15 S1 123.2(5) . . ?
C16 C15 C14 118.8(6) . . ?
C17 C16 C15 119.7(6) . . ?
C16 C17 C12 121.9(6) . . ?
C19 C18 S1 117.4(5) . . ?
C23 C18 S1 122.6(6) . . ?
C23 C18 C19 119.9(6) . . ?
C20 C19 C18 118.7(6) . . ?
C21 C20 C19 121.5(7) . . ?
C20 C21 C22 119.3(7) . . ?
C21 C22 C23 120.7(6) . . ?
C18 C23 C22 119.9(7) . . ?

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
S1 C15 C16 C17 172.1(5) . . . . ?
S1 C18 C19 C20 -177.0(5) . . . . ?
S1 C18 C23 C22 177.5(5) . . . . ?
O1 C1 C2 C3 -24.1(9) . . . . ?
O1 C1 C2 C12 100.9(7) . . . . ?
O2 C10 C11 N1 -8.0(7) . . . . ?
N1 C1 C2 C3 157.6(6) . . . . ?
N1 C1 C2 C12 -77.5(7) . . . . ?
C1 N1 C9 O2 -173.9(6) . . . . ?
C1 N1 C9 O3 5.3(12) . . . . ?
C1 N1 C11 C10 179.1(6) . . . . ?
C1 C2 C3 C4 85.5(7) . . . . ?
C1 C2 C3 C8 -95.4(7) . . . . ?
C1 C2 C12 C13 155.1(6) . . . . ?
C1 C2 C12 C17 -27.5(8) . . . . ?
C2 C3 C4 C5 178.2(6) . . . . ?
C2 C3 C8 C7 -178.8(6) . . . . ?
C2 C12 C13 C14 176.3(5) . . . . ?
C2 C12 C17 C16 -174.8(5) . . . . ?
C3 C2 C12 C13 -80.5(7) . . . . ?
C3 C2 C12 C17 97.0(6) . . . . ?
C3 C4 C5 C6 0.8(11) . . . . ?
C4 C3 C8 C7 0.4(10) . . . . ?
C4 C5 C6 C7 0.0(11) . . . . ?
C5 C6 C7 C8 -0.6(11) . . . . ?
C6 C7 C8 C3 0.4(11) . . . . ?
C8 C3 C4 C5 -1.0(10) . . . . ?
C9 O2 C10 C11 7.7(8) . . . . ?
C9 N1 C1 O1 170.4(6) . . . . ?
C9 N1 C1 C2 -11.2(10) . . . . ?
C9 N1 C11 C10 6.2(7) . . . . ?
C10 O2 C9 O3 176.9(7) . . . . ?
C10 O2 C9 N1 -3.8(7) . . . . ?
C11 N1 C1 O1 -1.1(9) . . . . ?
C11 N1 C1 C2 177.3(6) . . . . ?
C11 N1 C9 O2 -1.8(7) . . . . ?
C11 N1 C9 O3 177.4(7) . . . . ?
C12 C2 C3 C4 -38.5(8) . . . . ?
C12 C2 C3 C8 140.6(6) . . . . ?
C12 C13 C14 C15 -1.2(9) . . . . ?
C13 C12 C17 C16 2.8(9) . . . . ?
C13 C14 C15 S1 -171.0(5) . . . . ?
C13 C14 C15 C16 2.3(9) . . . . ?
C14 C15 C16 C17 -0.9(9) . . . . ?
C15 S1 C18 C19 -135.3(5) . . . . ?
C15 S1 C18 C23 48.8(7) . . . . ?
C15 C16 C17 C12 -1.7(9) . . . . ?
C17 C12 C13 C14 -1.3(9) . . . . ?
C18 S1 C15 C14 -148.4(5) . . . . ?
C18 S1 C15 C16 38.6(6) . . . . ?
C18 C19 C20 C21 -0.1(11) . . . . ?
C19 C18 C23 C22 1.8(10) . . . . ?
C19 C20 C21 C22 0.5(11) . . . . ?
C20 C21 C22 C23 0.3(11) . . . . ?
C21 C22 C23 C18 -1.4(10) . . . . ?
C23 C18 C19 C20 -1.0(10) . . . . ?


####################################################################### 
# 
# 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_mo_dakl346_pca21
_database_code_depnum_ccdc_archive 'CCDC 1540804'
_audit_update_record             
;
2017-03-29 deposited with the CCDC.
2018-03-26 downloaded from the CCDC.
;
_audit_creation_date             2017-03-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
'3-(1-cyclohexyl-2-oxo-2-(2-oxooxazolidin-3-yl)ethyl)-2-(methylthio)phenyl acetate'
_chemical_formula_moiety         'C20 H25 N O5 S'
_chemical_formula_sum            'C20 H25 N O5 S'
_chemical_formula_weight         391.48
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   11.7592(13)
_cell_length_b                   10.1198(10)
_cell_length_c                   32.161(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3827.2(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9017
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.320
_cell_measurement_theta_min      2.377
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction. 
wR2(int) was 0.1046 before and 0.0541 after correction. 
The Ratio of minimum to maximum transmission is 0.8549. 
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.024
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            100589
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.380
_diffrn_reflns_theta_min         2.378
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed  X-ray tube'
_diffrn_source_type              'Incoatec IuSMo'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.959
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                6782
_reflns_number_total             7014
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'APEX2 v2013.6-2'
_computing_data_collection       'APEX2 v2013.6-2'
_computing_data_reduction        'APEX2 v2013.6-2'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.754
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 
;
 Flack x determined using 3224 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.11(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         7014
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0716P)²+3.0440P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1156
_refine_special_details          
;
_olex2_refinement_description
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1A(H1A), C6A(H6A), C1B(H1B), C6B(H6B)
2.b Secondary CH2 refined with riding coordinates:
 C4A(H4AA,H4AB), C5A(H5AA,H5AB), C7A(H7AA,H7AB), C8A(H8AA,H8AB), C9A(H9AA,
 H9AB), C10A(H10A,H10B), C11A(H11A,H11B), C4B(H4BA,H4BB), C5B(H5BA,H5BB),
 C7B(H7BA,H7BB), C8B(H8BA,H8BB), C9B(H9BA,H9BB), C10B(H10C,H10D), C11B(H11C,
 H11D)
2.c Aromatic/amide H refined with riding coordinates:
 C15A(H15A), C16A(H16A), C17A(H17A), C15B(H15B), C16B(H16B), C17B(H17B)
2.d Idealised Me refined as rotating group:
 C18A(H18A,H18B,H18C), C20A(H20A,H20B,H20C), C18B(H18D,H18E,H18F), C20B(H20D,
 H20E,H20F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.86824(8) 0.18747(10) 0.42940(3) 0.0141(2) Uani 1 1 d . . . . .
O1A O 0.4449(3) 0.0549(3) 0.49151(9) 0.0222(7) Uani 1 1 d . . . . .
O2A O 0.4502(2) 0.2155(3) 0.36395(9) 0.0175(6) Uani 1 1 d . . . . .
O3A O 0.6083(2) 0.0013(3) 0.45997(10) 0.0201(7) Uani 1 1 d . . . . .
O4A O 0.9864(2) 0.4133(3) 0.39035(8) 0.0152(6) Uani 1 1 d . . . . .
O5A O 0.9353(3) 0.5202(3) 0.44876(10) 0.0244(7) Uani 1 1 d . . . . .
N1A N 0.4751(3) 0.1412(3) 0.42889(11) 0.0140(7) Uani 1 1 d . . . . .
C1A C 0.6397(3) 0.1395(4) 0.37882(11) 0.0096(8) Uani 1 1 d . . . . .
H1A H 0.6754 0.0913 0.4026 0.011 Uiso 1 1 calc R . . . .
C2A C 0.5156(3) 0.1679(4) 0.38895(13) 0.0124(8) Uani 1 1 d . . . . .
C3A C 0.5189(3) 0.0608(4) 0.45965(13) 0.0152(8) Uani 1 1 d . . . . .
C4A C 0.3508(4) 0.1455(5) 0.48436(16) 0.0256(11) Uani 1 1 d . . . . .
H4AA H 0.3605 0.2274 0.5008 0.031 Uiso 1 1 calc R . . . .
H4AB H 0.2775 0.1039 0.4920 0.031 Uiso 1 1 calc R . . . .
C5A C 0.3551(4) 0.1749(4) 0.43813(16) 0.0190(10) Uani 1 1 d . . . . .
H5AA H 0.3016 0.1185 0.4223 0.023 Uiso 1 1 calc R . . . .
H5AB H 0.3386 0.2690 0.4323 0.023 Uiso 1 1 calc R . . . .
C6A C 0.6427(3) 0.0501(4) 0.33938(13) 0.0119(9) Uani 1 1 d . . . . .
H6A H 0.5980 0.0950 0.3170 0.014 Uiso 1 1 calc R . . . .
C7A C 0.7640(3) 0.0300(4) 0.32359(13) 0.0139(8) Uani 1 1 d . . . . .
H7AA H 0.7976 0.1169 0.3165 0.017 Uiso 1 1 calc R . . . .
H7AB H 0.8106 -0.0100 0.3459 0.017 Uiso 1 1 calc R . . . .
C8A C 0.7671(4) -0.0590(4) 0.28534(13) 0.0180(9) Uani 1 1 d . . . . .
H8AA H 0.8470 -0.0734 0.2768 0.022 Uiso 1 1 calc R . . . .
H8AB H 0.7268 -0.0152 0.2621 0.022 Uiso 1 1 calc R . . . .
C9A C 0.7110(4) -0.1920(4) 0.29450(13) 0.0174(9) Uani 1 1 d . . . . .
H9AA H 0.7559 -0.2395 0.3158 0.021 Uiso 1 1 calc R . . . .
H9AB H 0.7106 -0.2463 0.2689 0.021 Uiso 1 1 calc R . . . .
C10A C 0.5891(4) -0.1742(4) 0.30998(13) 0.0172(8) Uani 1 1 d . . . . .
H10A H 0.5565 -0.2614 0.3172 0.021 Uiso 1 1 calc R . . . .
H10B H 0.5421 -0.1349 0.2876 0.021 Uiso 1 1 calc R . . . .
C11A C 0.5867(4) -0.0842(4) 0.34831(13) 0.0143(8) Uani 1 1 d . . . . .
H11A H 0.6273 -0.1280 0.3715 0.017 Uiso 1 1 calc R . . . .
H11B H 0.5069 -0.0701 0.3570 0.017 Uiso 1 1 calc R . . . .
C12A C 0.7037(3) 0.2682(4) 0.37147(12) 0.0096(7) Uani 1 1 d . . . . .
C13A C 0.8098(3) 0.2918(4) 0.39042(11) 0.0102(7) Uani 1 1 d . . . . .
C14A C 0.8740(3) 0.4009(4) 0.37720(12) 0.0110(8) Uani 1 1 d . . . . .
C15A C 0.8337(3) 0.4897(4) 0.34843(13) 0.0139(8) Uani 1 1 d . . . . .
H15A H 0.8780 0.5640 0.3405 0.017 Uiso 1 1 calc R . . . .
C16A C 0.7267(4) 0.4684(4) 0.33114(13) 0.0145(8) Uani 1 1 d . . . . .
H16A H 0.6964 0.5303 0.3119 0.017 Uiso 1 1 calc R . . . .
C17A C 0.6645(3) 0.3580(4) 0.34182(12) 0.0127(8) Uani 1 1 d . . . . .
H17A H 0.5934 0.3426 0.3287 0.015 Uiso 1 1 calc R . . . .
C18A C 0.7909(4) 0.2449(4) 0.47478(13) 0.0203(9) Uani 1 1 d . . . . .
H18A H 0.7092 0.2445 0.4688 0.030 Uiso 1 1 calc GR . . . .
H18B H 0.8152 0.3350 0.4817 0.030 Uiso 1 1 calc GR . . . .
H18C H 0.8066 0.1863 0.4983 0.030 Uiso 1 1 calc GR . . . .
C19A C 1.0063(4) 0.4652(4) 0.42868(14) 0.0157(8) Uani 1 1 d . . . . .
C20A C 1.1282(4) 0.4424(5) 0.44055(15) 0.0255(10) Uani 1 1 d . . . . .
H20A H 1.1399 0.3484 0.4465 0.038 Uiso 1 1 calc GR . . . .
H20B H 1.1465 0.4946 0.4653 0.038 Uiso 1 1 calc GR . . . .
H20C H 1.1778 0.4692 0.4176 0.038 Uiso 1 1 calc GR . . . .
S1B S -0.14502(8) 0.31755(9) 0.10236(3) 0.0117(2) Uani 1 1 d . . . . .
O1B O 0.2803(2) 0.4356(3) 0.03931(9) 0.0224(7) Uani 1 1 d . . . . .
O2B O 0.2736(2) 0.2853(3) 0.16819(9) 0.0153(6) Uani 1 1 d . . . . .
O3B O 0.1187(3) 0.4949(3) 0.07008(10) 0.0206(7) Uani 1 1 d . . . . .
O4B O -0.2642(2) 0.0899(3) 0.14050(8) 0.0143(6) Uani 1 1 d . . . . .
O5B O -0.2129(3) -0.0117(3) 0.08103(10) 0.0206(7) Uani 1 1 d . . . . .
N1B N 0.2503(3) 0.3532(3) 0.10281(11) 0.0129(6) Uani 1 1 d . . . . .
C1B C 0.0846(3) 0.3615(3) 0.15279(12) 0.0094(7) Uani 1 1 d . . . . .
H1B H 0.0496 0.4104 0.1290 0.011 Uiso 1 1 calc R . . . .
C2B C 0.2080(3) 0.3312(4) 0.14262(12) 0.0094(8) Uani 1 1 d . . . . .
C3B C 0.2058(3) 0.4346(4) 0.07106(13) 0.0161(9) Uani 1 1 d . . . . .
C4B C 0.3744(4) 0.3456(5) 0.04737(15) 0.0242(10) Uani 1 1 d . . . . .
H4BA H 0.4476 0.3866 0.0394 0.029 Uiso 1 1 calc R . . . .
H4BB H 0.3648 0.2625 0.0315 0.029 Uiso 1 1 calc R . . . .
C5B C 0.3710(4) 0.3183(4) 0.09447(14) 0.0163(10) Uani 1 1 d . . . . .
H5BA H 0.3872 0.2246 0.1009 0.020 Uiso 1 1 calc R . . . .
H5BB H 0.4242 0.3759 0.1100 0.020 Uiso 1 1 calc R . . . .
C6B C 0.0812(3) 0.4500(4) 0.19197(12) 0.0093(8) Uani 1 1 d . . . . .
H6B H 0.1255 0.4052 0.2144 0.011 Uiso 1 1 calc R . . . .
C7B C -0.0405(3) 0.4701(4) 0.20744(12) 0.0116(8) Uani 1 1 d . . . . .
H7BA H -0.0743 0.3833 0.2145 0.014 Uiso 1 1 calc R . . . .
H7BB H -0.0868 0.5100 0.1850 0.014 Uiso 1 1 calc R . . . .
C8B C -0.0436(4) 0.5599(4) 0.24581(13) 0.0163(9) Uani 1 1 d . . . . .
H8BA H -0.1235 0.5746 0.2543 0.020 Uiso 1 1 calc R . . . .
H8BB H -0.0037 0.5160 0.2691 0.020 Uiso 1 1 calc R . . . .
C9B C 0.0127(4) 0.6925(4) 0.23688(13) 0.0170(9) Uani 1 1 d . . . . .
H9BA H -0.0323 0.7407 0.2157 0.020 Uiso 1 1 calc R . . . .
H9BB H 0.0136 0.7463 0.2626 0.020 Uiso 1 1 calc R . . . .
C10B C 0.1338(4) 0.6747(4) 0.22125(13) 0.0152(8) Uani 1 1 d . . . . .
H10C H 0.1812 0.6361 0.2436 0.018 Uiso 1 1 calc R . . . .
H10D H 0.1661 0.7619 0.2139 0.018 Uiso 1 1 calc R . . . .
C11B C 0.1370(3) 0.5840(4) 0.18307(13) 0.0114(9) Uani 1 1 d . . . . .
H11C H 0.2170 0.5698 0.1746 0.014 Uiso 1 1 calc R . . . .
H11D H 0.0969 0.6274 0.1597 0.014 Uiso 1 1 calc R . . . .
C12B C 0.0191(3) 0.2333(4) 0.15992(11) 0.0085(7) Uani 1 1 d . . . . .
C13B C -0.0873(3) 0.2107(4) 0.14097(12) 0.0102(7) Uani 1 1 d . . . . .
C14B C -0.1509(3) 0.1015(4) 0.15373(12) 0.0119(8) Uani 1 1 d . . . . .
C15B C -0.1110(3) 0.0114(4) 0.18217(13) 0.0136(8) Uani 1 1 d . . . . .
H15B H -0.1554 -0.0632 0.1898 0.016 Uiso 1 1 calc R . . . .
C16B C -0.0042(4) 0.0316(4) 0.19960(12) 0.0153(8) Uani 1 1 d . . . . .
H16B H 0.0255 -0.0305 0.2189 0.018 Uiso 1 1 calc R . . . .
C17B C 0.0588(3) 0.1417(4) 0.18892(11) 0.0111(8) Uani 1 1 d . . . . .
H17B H 0.1308 0.1554 0.2016 0.013 Uiso 1 1 calc R . . . .
C18B C -0.0670(4) 0.2601(4) 0.05719(13) 0.0187(9) Uani 1 1 d . . . . .
H18D H -0.0810 0.3198 0.0338 0.028 Uiso 1 1 calc GR . . . .
H18E H -0.0923 0.1708 0.0499 0.028 Uiso 1 1 calc GR . . . .
H18F H 0.0145 0.2587 0.0635 0.028 Uiso 1 1 calc GR . . . .
C19B C -0.2844(3) 0.0424(4) 0.10144(14) 0.0154(8) Uani 1 1 d . . . . .
C20B C -0.4049(4) 0.0690(5) 0.08992(15) 0.0242(10) Uani 1 1 d . . . . .
H20D H -0.4550 0.0406 0.1126 0.036 Uiso 1 1 calc GR . . . .
H20E H -0.4240 0.0201 0.0646 0.036 Uiso 1 1 calc GR . . . .
H20F H -0.4151 0.1639 0.0850 0.036 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1A C13A 1.777(4) . ?
S1A C18A 1.815(4) . ?
O1A C3A 1.345(5) . ?
O1A C4A 1.456(6) . ?
O2A C2A 1.213(5) . ?
O3A C3A 1.211(5) . ?
O4A C14A 1.394(5) . ?
O4A C19A 1.360(5) . ?
O5A C19A 1.194(6) . ?
N1A C2A 1.397(5) . ?
N1A C3A 1.380(6) . ?
N1A C5A 1.482(5) . ?
C1A H1A 1.0000 . ?
C1A C2A 1.523(5) . ?
C1A C6A 1.558(5) . ?
C1A C12A 1.522(5) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C4A C5A 1.517(7) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C6A H6A 1.0000 . ?
C6A C7A 1.528(6) . ?
C6A C11A 1.537(5) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C7A C8A 1.525(6) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A C9A 1.528(6) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C9A C10A 1.528(6) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C10A C11A 1.533(6) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C12A C13A 1.409(5) . ?
C12A C17A 1.395(5) . ?
C13A C14A 1.404(5) . ?
C14A C15A 1.374(6) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.392(6) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.379(6) . ?
C17A H17A 0.9500 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C19A C20A 1.501(6) . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
S1B C13B 1.781(4) . ?
S1B C18B 1.814(4) . ?
O1B C3B 1.346(5) . ?
O1B C4B 1.456(6) . ?
O2B C2B 1.219(5) . ?
O3B C3B 1.192(5) . ?
O4B C14B 1.403(5) . ?
O4B C19B 1.366(5) . ?
O5B C19B 1.199(5) . ?
N1B C2B 1.391(5) . ?
N1B C3B 1.413(5) . ?
N1B C5B 1.486(5) . ?
C1B H1B 1.0000 . ?
C1B C2B 1.520(5) . ?
C1B C6B 1.546(5) . ?
C1B C12B 1.526(5) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C4B C5B 1.540(7) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C6B H6B 1.0000 . ?
C6B C7B 1.529(5) . ?
C6B C11B 1.534(5) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C7B C8B 1.533(5) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C8B C9B 1.523(6) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C9B C10B 1.521(6) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C10B C11B 1.533(6) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12B C13B 1.411(5) . ?
C12B C17B 1.396(5) . ?
C13B C14B 1.395(6) . ?
C14B C15B 1.375(6) . ?
C15B H15B 0.9500 . ?
C15B C16B 1.390(6) . ?
C16B H16B 0.9500 . ?
C16B C17B 1.382(5) . ?
C17B H17B 0.9500 . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
C19B C20B 1.489(6) . ?
C20B H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13A S1A C18A 100.54(19) . . ?
C3A O1A C4A 110.1(3) . . ?
C19A O4A C14A 118.3(3) . . ?
C2A N1A C5A 117.7(3) . . ?
C3A N1A C2A 130.2(3) . . ?
C3A N1A C5A 110.3(3) . . ?
C2A C1A H1A 109.3 . . ?
C2A C1A C6A 107.8(3) . . ?
C6A C1A H1A 109.3 . . ?
C12A C1A H1A 109.3 . . ?
C12A C1A C2A 110.2(3) . . ?
C12A C1A C6A 111.1(3) . . ?
O2A C2A N1A 118.0(4) . . ?
O2A C2A C1A 122.8(4) . . ?
N1A C2A C1A 119.2(3) . . ?
O1A C3A N1A 109.3(4) . . ?
O3A C3A O1A 122.2(4) . . ?
O3A C3A N1A 128.5(4) . . ?
O1A C4A H4AA 110.8 . . ?
O1A C4A H4AB 110.8 . . ?
O1A C4A C5A 104.6(3) . . ?
H4AA C4A H4AB 108.9 . . ?
C5A C4A H4AA 110.8 . . ?
C5A C4A H4AB 110.8 . . ?
N1A C5A C4A 100.6(4) . . ?
N1A C5A H5AA 111.7 . . ?
N1A C5A H5AB 111.7 . . ?
C4A C5A H5AA 111.7 . . ?
C4A C5A H5AB 111.7 . . ?
H5AA C5A H5AB 109.4 . . ?
C1A C6A H6A 108.1 . . ?
C7A C6A C1A 111.6(3) . . ?
C7A C6A H6A 108.1 . . ?
C7A C6A C11A 110.1(3) . . ?
C11A C6A C1A 110.6(3) . . ?
C11A C6A H6A 108.1 . . ?
C6A C7A H7AA 109.3 . . ?
C6A C7A H7AB 109.3 . . ?
H7AA C7A H7AB 107.9 . . ?
C8A C7A C6A 111.7(3) . . ?
C8A C7A H7AA 109.3 . . ?
C8A C7A H7AB 109.3 . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
C7A C8A C9A 110.8(3) . . ?
H8AA C8A H8AB 108.1 . . ?
C9A C8A H8AA 109.5 . . ?
C9A C8A H8AB 109.5 . . ?
C8A C9A H9AA 109.4 . . ?
C8A C9A H9AB 109.4 . . ?
C8A C9A C10A 111.4(3) . . ?
H9AA C9A H9AB 108.0 . . ?
C10A C9A H9AA 109.4 . . ?
C10A C9A H9AB 109.4 . . ?
C9A C10A H10A 109.6 . . ?
C9A C10A H10B 109.6 . . ?
C9A C10A C11A 110.4(3) . . ?
H10A C10A H10B 108.1 . . ?
C11A C10A H10A 109.6 . . ?
C11A C10A H10B 109.6 . . ?
C6A C11A H11A 109.3 . . ?
C6A C11A H11B 109.3 . . ?
C10A C11A C6A 111.6(3) . . ?
C10A C11A H11A 109.3 . . ?
C10A C11A H11B 109.3 . . ?
H11A C11A H11B 108.0 . . ?
C13A C12A C1A 121.0(3) . . ?
C17A C12A C1A 120.0(3) . . ?
C17A C12A C13A 118.5(3) . . ?
C12A C13A S1A 123.2(3) . . ?
C14A C13A S1A 118.2(3) . . ?
C14A C13A C12A 118.6(3) . . ?
O4A C14A C13A 119.3(3) . . ?
C15A C14A O4A 118.2(3) . . ?
C15A C14A C13A 122.2(3) . . ?
C14A C15A H15A 120.7 . . ?
C14A C15A C16A 118.6(4) . . ?
C16A C15A H15A 120.7 . . ?
C15A C16A H16A 119.8 . . ?
C17A C16A C15A 120.3(4) . . ?
C17A C16A H16A 119.8 . . ?
C12A C17A H17A 119.2 . . ?
C16A C17A C12A 121.5(4) . . ?
C16A C17A H17A 119.2 . . ?
S1A C18A H18A 109.5 . . ?
S1A C18A H18B 109.5 . . ?
S1A C18A H18C 109.5 . . ?
H18A C18A H18B 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
O4A C19A C20A 109.6(4) . . ?
O5A C19A O4A 123.3(4) . . ?
O5A C19A C20A 127.0(4) . . ?
C19A C20A H20A 109.5 . . ?
C19A C20A H20B 109.5 . . ?
C19A C20A H20C 109.5 . . ?
H20A C20A H20B 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C13B S1B C18B 99.85(19) . . ?
C3B O1B C4B 110.8(3) . . ?
C19B O4B C14B 118.3(3) . . ?
C2B N1B C3B 128.7(3) . . ?
C2B N1B C5B 118.0(3) . . ?
C3B N1B C5B 111.2(3) . . ?
C2B C1B H1B 109.1 . . ?
C2B C1B C6B 108.5(3) . . ?
C2B C1B C12B 110.0(3) . . ?
C6B C1B H1B 109.1 . . ?
C12B C1B H1B 109.1 . . ?
C12B C1B C6B 110.9(3) . . ?
O2B C2B N1B 117.1(3) . . ?
O2B C2B C1B 122.4(3) . . ?
N1B C2B C1B 120.5(3) . . ?
O1B C3B N1B 108.1(4) . . ?
O3B C3B O1B 122.4(4) . . ?
O3B C3B N1B 129.5(4) . . ?
O1B C4B H4BA 110.6 . . ?
O1B C4B H4BB 110.6 . . ?
O1B C4B C5B 105.5(3) . . ?
H4BA C4B H4BB 108.8 . . ?
C5B C4B H4BA 110.6 . . ?
C5B C4B H4BB 110.6 . . ?
N1B C5B C4B 99.2(4) . . ?
N1B C5B H5BA 111.9 . . ?
N1B C5B H5BB 111.9 . . ?
C4B C5B H5BA 111.9 . . ?
C4B C5B H5BB 111.9 . . ?
H5BA C5B H5BB 109.6 . . ?
C1B C6B H6B 108.2 . . ?
C7B C6B C1B 111.5(3) . . ?
C7B C6B H6B 108.2 . . ?
C7B C6B C11B 110.1(3) . . ?
C11B C6B C1B 110.4(3) . . ?
C11B C6B H6B 108.2 . . ?
C6B C7B H7BA 109.4 . . ?
C6B C7B H7BB 109.4 . . ?
C6B C7B C8B 111.3(3) . . ?
H7BA C7B H7BB 108.0 . . ?
C8B C7B H7BA 109.4 . . ?
C8B C7B H7BB 109.4 . . ?
C7B C8B H8BA 109.4 . . ?
C7B C8B H8BB 109.4 . . ?
H8BA C8B H8BB 108.0 . . ?
C9B C8B C7B 111.1(3) . . ?
C9B C8B H8BA 109.4 . . ?
C9B C8B H8BB 109.4 . . ?
C8B C9B H9BA 109.3 . . ?
C8B C9B H9BB 109.3 . . ?
H9BA C9B H9BB 108.0 . . ?
C10B C9B C8B 111.4(3) . . ?
C10B C9B H9BA 109.3 . . ?
C10B C9B H9BB 109.3 . . ?
C9B C10B H10C 109.4 . . ?
C9B C10B H10D 109.4 . . ?
C9B C10B C11B 111.0(3) . . ?
H10C C10B H10D 108.0 . . ?
C11B C10B H10C 109.4 . . ?
C11B C10B H10D 109.4 . . ?
C6B C11B H11C 109.3 . . ?
C6B C11B H11D 109.3 . . ?
C10B C11B C6B 111.7(3) . . ?
C10B C11B H11C 109.3 . . ?
C10B C11B H11D 109.3 . . ?
H11C C11B H11D 107.9 . . ?
C13B C12B C1B 121.4(3) . . ?
C17B C12B C1B 119.8(3) . . ?
C17B C12B C13B 118.5(3) . . ?
C12B C13B S1B 122.7(3) . . ?
C14B C13B S1B 118.8(3) . . ?
C14B C13B C12B 118.5(3) . . ?
C13B C14B O4B 119.1(4) . . ?
C15B C14B O4B 118.0(4) . . ?
C15B C14B C13B 122.6(4) . . ?
C14B C15B H15B 120.7 . . ?
C14B C15B C16B 118.6(4) . . ?
C16B C15B H15B 120.7 . . ?
C15B C16B H16B 119.9 . . ?
C17B C16B C15B 120.2(4) . . ?
C17B C16B H16B 119.9 . . ?
C12B C17B H17B 119.2 . . ?
C16B C17B C12B 121.5(3) . . ?
C16B C17B H17B 119.2 . . ?
S1B C18B H18D 109.5 . . ?
S1B C18B H18E 109.5 . . ?
S1B C18B H18F 109.5 . . ?
H18D C18B H18E 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
O4B C19B C20B 109.3(4) . . ?
O5B C19B O4B 122.8(4) . . ?
O5B C19B C20B 127.8(4) . . ?
C19B C20B H20D 109.5 . . ?
C19B C20B H20E 109.5 . . ?
C19B C20B H20F 109.5 . . ?
H20D C20B H20E 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?

