# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_compound_8a
_database_code_depnum_ccdc_archive 'CCDC 2158145'
loop_
_audit_author_name
_audit_author_address
'Christian Jandl'
;Technical University of Munich
Germany
;
_audit_update_record             
;
2022-03-12 deposited with the CCDC.	2022-09-19 downloaded from the CCDC.
;

#===============================================================================

#start validation reply form
_vrf_PLAT934_compound_8a         
;
PROBLEM:   Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers .. 2 Check
RESPONSE: Only twinned crystals of this sample could be found, therefore
 more outliers and a poor standard uncertainty of the Flack parameter are
 observed.
;
#end validation reply form 

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 O2'
_chemical_formula_structural     ?
_chemical_formula_sum            'C17 H18 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         254.31
_chemical_compound_source        'see text'

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'
O O 0.0106 0.0060 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z

_cell_length_a                   6.4440(8)
_cell_length_b                   8.3645(11)
_cell_length_c                   24.703(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1331.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9898
_cell_measurement_theta_min      2.9401
_cell_measurement_theta_max      26.3368
_cell_special_details            
;
;

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.032
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.082
_exptl_crystal_density_meas_temp ?

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2, Bruker, 2016'
_exptl_absorpt_correction_T_min  0.6140
_exptl_absorpt_correction_T_max  0.7454

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
Diffractometer operator             C. Jandl
scanspeed                           10-60s per frame
dx                                  50 mm
2341 frames measured in 8 data sets
phi-scans with delta_phi         = 0.5
omega-scans with delta_omega     = 0.5
shutterless mode
;
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'IMS microsource'
_diffrn_radiation_monochromator  'Helios optic'

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker Photon CMOS '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' CMOS plate '
_diffrn_detector_area_resol_mean 16

# number of measured reflections (redundant set)
_diffrn_reflns_number            35906
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             2734
# number of observed reflections (> n sig(I))
_reflns_number_gt                2578
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX III Control Software (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2017)'
_computing_data_reduction        'SAINT (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL-2017 (Sheldrick, 2017), SHELXLE (Huebschle, 2011)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2004)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.,Twin
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'W=1/[Σ²(FO²)+(0.0365P)²+0.4516P] 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_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.4(17)

# Permitted for _chemical_absolute_configuration:
# Absolute configuration details
# rm   = Det. by chiral ref. mol. with known abs.conf
# ad   = Det. by anomalous dispersion
# rmad = Det. by 'rm' and 'ad'
# syn  = Det. with reference to synthesis
# unk  = Unknown/Arbitrary
_chemical_absolute_configuration unk

_refine_ls_number_reflns         2734
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0871
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.040

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O Uani 0.4595(3) 0.31888(18) 0.36121(6) 1.000 0.0248(5) d . . .
O2 O Uani 0.6308(3) 0.6101(2) 0.28978(7) 1.000 0.0325(5) d . . .
C1 C Uani 0.2687(4) 0.2969(3) 0.33256(9) 1.000 0.0255(7) d . . .
C2 C Uani 0.1471(4) 0.4533(2) 0.33338(8) 1.000 0.0202(6) d . . .
C3 C Uani 0.1109(4) 0.4963(2) 0.39257(8) 1.000 0.0193(6) d . . .
C4 C Uani 0.2435(3) 0.4420(2) 0.43201(8) 1.000 0.0183(6) d . . .
C5 C Uani 0.4282(4) 0.3381(3) 0.41795(9) 1.000 0.0232(7) d . . .
C6 C Uani -0.0677(4) 0.5852(3) 0.40735(9) 1.000 0.0230(6) d . . .
C7 C Uani -0.1122(4) 0.6172(3) 0.46016(9) 1.000 0.0229(6) d . . .
C8 C Uani 0.0216(4) 0.5634(2) 0.50194(8) 1.000 0.0196(6) d . . .
C9 C Uani 0.2031(3) 0.4755(2) 0.48805(8) 1.000 0.0180(6) d . . .
C10 C Uani 0.3354(4) 0.4242(3) 0.53065(9) 1.000 0.0241(6) d . . .
C11 C Uani 0.2892(4) 0.4585(3) 0.58356(9) 1.000 0.0274(7) d . . .
C12 C Uani 0.1094(4) 0.5445(3) 0.59693(9) 1.000 0.0259(7) d . . .
C13 C Uani -0.0219(4) 0.5960(3) 0.55722(8) 1.000 0.0237(7) d . . .
C14 C Uani 0.2581(4) 0.5856(3) 0.29911(8) 1.000 0.0206(6) d . . .
C15 C Uani 0.4788(4) 0.6081(2) 0.31845(9) 1.000 0.0216(6) d . . .
C16 C Uani 0.1546(4) 0.7505(3) 0.30684(10) 1.000 0.0263(7) d . . .
C17 C Uani 0.2533(4) 0.5437(3) 0.23874(8) 1.000 0.0286(7) d . . .
H1A H Uiso 0.18625 0.21116 0.34989 1.000 0.0310 c RU . .
H1B H Uiso 0.29758 0.26503 0.29471 1.000 0.0310 c RU . .
H2 H Uiso 0.00862 0.43265 0.31650 1.000 0.0240 c RU . .
H5A H Uiso 0.55455 0.38597 0.43398 1.000 0.0280 c RU . .
H5B H Uiso 0.40865 0.23140 0.43451 1.000 0.0280 c RU . .
H6 H Uiso -0.15811 0.62330 0.37986 1.000 0.0280 c RU . .
H7 H Uiso -0.23366 0.67592 0.46906 1.000 0.0280 c RU . .
H10 H Uiso 0.45745 0.36545 0.52236 1.000 0.0290 c RU . .
H11 H Uiso 0.37994 0.42360 0.61148 1.000 0.0330 c RU . .
H12 H Uiso 0.07895 0.56699 0.63378 1.000 0.0310 c RU . .
H13 H Uiso -0.14328 0.65412 0.56663 1.000 0.0280 c RU . .
H15 H Uiso 0.49968 0.62184 0.35623 1.000 0.0260 c RU . .
H16A H Uiso 0.22154 0.82885 0.28306 1.000 0.0390 c RU . .
H16B H Uiso 0.16972 0.78440 0.34461 1.000 0.0390 c RU . .
H16C H Uiso 0.00691 0.74291 0.29775 1.000 0.0390 c RU . .
H17A H Uiso 0.32456 0.62744 0.21812 1.000 0.0430 c RU . .
H17B H Uiso 0.10893 0.53585 0.22657 1.000 0.0430 c RU . .
H17C H Uiso 0.32336 0.44118 0.23293 1.000 0.0430 c RU . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.431(3) . . yes
O1 C5 1.425(3) . . yes
O2 C15 1.209(3) . . yes
C1 C2 1.525(3) . . no
C2 C3 1.524(3) . . no
C2 C14 1.566(3) . . no
C3 C4 1.373(3) . . no
C3 C6 1.418(3) . . no
C4 C5 1.514(3) . . no
C4 C9 1.436(3) . . no
C6 C7 1.362(3) . . no
C7 C8 1.418(3) . . no
C8 C9 1.424(3) . . no
C8 C13 1.421(3) . . no
C9 C10 1.421(3) . . no
C10 C11 1.371(3) . . no
C11 C12 1.403(4) . . no
C12 C13 1.365(3) . . no
C14 C15 1.512(4) . . no
C14 C16 1.544(4) . . no
C14 C17 1.532(3) . . no
C1 H1A 0.9900 . . no
C1 H1B 0.9900 . . no
C2 H2 1.0000 . . no
C5 H5A 0.9900 . . no
C5 H5B 0.9900 . . no
C6 H6 0.9500 . . no
C7 H7 0.9500 . . no
C10 H10 0.9500 . . no
C11 H11 0.9500 . . no
C12 H12 0.9500 . . no
C13 H13 0.9500 . . no
C15 H15 0.9500 . . no
C16 H16A 0.9800 . . no
C16 H16B 0.9800 . . no
C16 H16C 0.9800 . . no
C17 H17A 0.9800 . . no
C17 H17B 0.9800 . . no
C17 H17C 0.9800 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C5 112.30(19) . . . yes
O1 C1 C2 108.95(19) . . . yes
C1 C2 C3 107.09(16) . . . no
C1 C2 C14 111.4(2) . . . no
C3 C2 C14 114.95(16) . . . no
C2 C3 C4 120.5(2) . . . no
C2 C3 C6 119.7(2) . . . no
C4 C3 C6 119.72(19) . . . no
C3 C4 C5 121.08(18) . . . no
C3 C4 C9 120.44(18) . . . no
C5 C4 C9 118.40(17) . . . no
O1 C5 C4 113.68(19) . . . yes
C3 C6 C7 121.4(2) . . . no
C6 C7 C8 120.4(2) . . . no
C7 C8 C9 119.21(19) . . . no
C7 C8 C13 121.3(2) . . . no
C9 C8 C13 119.5(2) . . . no
C4 C9 C8 118.82(17) . . . no
C4 C9 C10 123.11(18) . . . no
C8 C9 C10 118.07(19) . . . no
C9 C10 C11 120.8(2) . . . no
C10 C11 C12 120.7(2) . . . no
C11 C12 C13 120.3(2) . . . no
C8 C13 C12 120.5(2) . . . no
C2 C14 C15 110.29(18) . . . no
C2 C14 C16 111.54(19) . . . no
C2 C14 C17 110.81(19) . . . no
C15 C14 C16 104.84(19) . . . no
C15 C14 C17 110.8(2) . . . no
C16 C14 C17 108.42(19) . . . no
O2 C15 C14 125.4(2) . . . yes
O1 C1 H1A 110.00 . . . no
O1 C1 H1B 110.00 . . . no
C2 C1 H1A 110.00 . . . no
C2 C1 H1B 110.00 . . . no
H1A C1 H1B 108.00 . . . no
C1 C2 H2 108.00 . . . no
C3 C2 H2 108.00 . . . no
C14 C2 H2 108.00 . . . no
O1 C5 H5A 109.00 . . . no
O1 C5 H5B 109.00 . . . no
C4 C5 H5A 109.00 . . . no
C4 C5 H5B 109.00 . . . no
H5A C5 H5B 108.00 . . . no
C3 C6 H6 119.00 . . . no
C7 C6 H6 119.00 . . . no
C6 C7 H7 120.00 . . . no
C8 C7 H7 120.00 . . . no
C9 C10 H10 120.00 . . . no
C11 C10 H10 120.00 . . . no
C10 C11 H11 120.00 . . . no
C12 C11 H11 120.00 . . . no
C11 C12 H12 120.00 . . . no
C13 C12 H12 120.00 . . . no
C8 C13 H13 120.00 . . . no
C12 C13 H13 120.00 . . . no
O2 C15 H15 117.00 . . . no
C14 C15 H15 117.00 . . . no
C14 C16 H16A 109.00 . . . no
C14 C16 H16B 109.00 . . . no
C14 C16 H16C 109.00 . . . no
H16A C16 H16B 109.00 . . . no
H16A C16 H16C 109.00 . . . no
H16B C16 H16C 109.00 . . . no
C14 C17 H17A 109.00 . . . no
C14 C17 H17B 109.00 . . . no
C14 C17 H17C 109.00 . . . no
H17A C17 H17B 109.00 . . . no
H17A C17 H17C 109.00 . . . no
H17B C17 H17C 110.00 . . . no

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 O1 C1 C2 69.6(2) . . . . no
C1 O1 C5 C4 -40.9(3) . . . . no
O1 C1 C2 C3 -58.8(2) . . . . no
O1 C1 C2 C14 67.7(2) . . . . no
C1 C2 C3 C4 25.5(3) . . . . no
C1 C2 C3 C6 -150.8(2) . . . . no
C14 C2 C3 C4 -98.8(2) . . . . no
C14 C2 C3 C6 84.9(3) . . . . no
C1 C2 C14 C15 -55.2(2) . . . . no
C1 C2 C14 C16 -171.26(19) . . . . no
C1 C2 C14 C17 67.9(2) . . . . no
C3 C2 C14 C15 66.8(3) . . . . no
C3 C2 C14 C16 -49.3(3) . . . . no
C3 C2 C14 C17 -170.1(2) . . . . no
C2 C3 C4 C5 -0.1(3) . . . . no
C2 C3 C4 C9 -176.68(17) . . . . no
C6 C3 C4 C5 176.2(2) . . . . no
C6 C3 C4 C9 -0.4(3) . . . . no
C2 C3 C6 C7 175.8(2) . . . . no
C4 C3 C6 C7 -0.5(3) . . . . no
C3 C4 C5 O1 6.2(3) . . . . no
C9 C4 C5 O1 -177.18(17) . . . . no
C3 C4 C9 C8 1.1(3) . . . . no
C3 C4 C9 C10 -179.3(2) . . . . no
C5 C4 C9 C8 -175.55(18) . . . . no
C5 C4 C9 C10 4.1(3) . . . . no
C3 C6 C7 C8 0.7(4) . . . . no
C6 C7 C8 C9 0.0(3) . . . . no
C6 C7 C8 C13 179.8(2) . . . . no
C7 C8 C9 C4 -0.9(3) . . . . no
C7 C8 C9 C10 179.5(2) . . . . no
C13 C8 C9 C4 179.29(19) . . . . no
C13 C8 C9 C10 -0.4(3) . . . . no
C7 C8 C13 C12 -179.5(2) . . . . no
C9 C8 C13 C12 0.4(3) . . . . no
C4 C9 C10 C11 -179.6(2) . . . . no
C8 C9 C10 C11 0.0(3) . . . . no
C9 C10 C11 C12 0.3(4) . . . . no
C10 C11 C12 C13 -0.3(4) . . . . no
C11 C12 C13 C8 0.0(4) . . . . no
C2 C14 C15 O2 130.4(2) . . . . no
C16 C14 C15 O2 -109.4(2) . . . . no
C17 C14 C15 O2 7.4(3) . . . . no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C1 H1B O2 0.9900 2.5000 3.463(3) 164.00 4_645 yes


####################################################################### 
# 
# 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_compound_8m
_database_code_depnum_ccdc_archive 'CCDC 2158146'
loop_
_audit_author_name
_audit_author_address
'Christian Jandl'
;Technical University of Munich
Germany
;
_audit_update_record             
;
2022-03-12 deposited with the CCDC.	2022-09-19 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 Cl O2'
_chemical_formula_structural     ?
_chemical_formula_sum            'C17 H17 Cl O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         288.76
_chemical_compound_source        'see text'

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'
O O 0.0106 0.0060 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 21'
_symmetry_Int_Tables_number      4

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

_cell_length_a                   6.0803(3)
_cell_length_b                   8.5188(4)
_cell_length_c                   13.8407(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.320(2)
_cell_angle_gamma                90
_cell_volume                     716.89(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    123
_cell_measurement_reflns_used    9872
_cell_measurement_theta_min      2.8077
_cell_measurement_theta_max      28.3564
_cell_special_details            
;
;

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.099
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.265
_exptl_crystal_density_meas_temp ?

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2, Bruker, 2016'
_exptl_absorpt_correction_T_min  0.7193
_exptl_absorpt_correction_T_max  0.7457

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
Diffractometer operator             C. Jandl
scanspeed                           1-10 s per frame
dx                                  34 mm
2009 frames measured in 10 data sets
phi-scans with delta_phi         = 0.5
omega-scans with delta_omega     = 0.5
shutterless mode
;
_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'TXS rotating anode'
_diffrn_radiation_monochromator  'Helios optic'

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker D8 Venture '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' Bruker Photon-100 CMOS '
_diffrn_detector_area_resol_mean 16

# number of measured reflections (redundant set)
_diffrn_reflns_number            24577
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             3555
# number of observed reflections (> n sig(I))
_reflns_number_gt                3527
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX III Control Software (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL (Sheldrick, 2018), SHELXLE (Huebschle, 2011)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2004)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'W=1/[Σ²(FO²)+(0.0336P)²+0.1944P] 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_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.015(7)

# Permitted for _chemical_absolute_configuration:
# Absolute configuration details
# rm   = Det. by chiral ref. mol. with known abs.conf
# ad   = Det. by anomalous dispersion
# rmad = Det. by 'rm' and 'ad'
# syn  = Det. with reference to synthesis
# unk  = Unknown/Arbitrary
_chemical_absolute_configuration ad

_refine_ls_number_reflns         3555
_refine_ls_number_parameters     183
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0667
_refine_ls_wR_factor_gt          0.0665
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.040

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl Uani 0.27122(9) 0.43045(6) 0.24174(3) 1.000 0.0320(1) d . . .
O1 O Uani 0.4782(2) 0.27439(17) 0.81897(9) 1.000 0.0285(4) d . . .
O2 O Uani 0.6609(2) 0.5767(2) 0.93251(11) 1.000 0.0387(5) d . . .
C1 C Uani 0.2875(3) 0.4225(2) 0.36688(10) 1.000 0.0218(4) d . . .
C2 C Uani 0.4626(3) 0.3394(2) 0.40973(12) 1.000 0.0236(5) d . . .
C3 C Uani 0.4744(3) 0.3288(2) 0.50845(12) 1.000 0.0206(4) d . . .
C4 C Uani 0.3142(2) 0.40077(17) 0.56858(11) 1.000 0.0153(4) d . . .
C5 C Uani 0.1430(3) 0.48770(19) 0.52354(11) 1.000 0.0164(4) d . . .
C6 C Uani 0.1322(3) 0.4964(2) 0.42134(12) 1.000 0.0210(4) d . . .
C7 C Uani 0.3179(3) 0.38587(17) 0.67133(11) 1.000 0.0155(4) d . . .
C8 C Uani 0.1616(2) 0.46009(17) 0.72705(10) 1.000 0.0150(4) d . . .
C9 C Uani -0.0048(3) 0.5502(2) 0.68059(11) 1.000 0.0192(4) d . . .
C10 C Uani -0.0151(3) 0.5633(2) 0.58234(12) 1.000 0.0215(4) d . . .
C11 C Uani 0.4847(3) 0.2776(2) 0.71689(12) 1.000 0.0253(4) d . . .
C12 C Uani 0.2572(3) 0.2725(2) 0.85427(13) 1.000 0.0271(5) d . . .
C13 C Uani 0.1559(2) 0.4335(2) 0.83571(10) 1.000 0.0174(4) d . . .
C14 C Uani 0.2711(2) 0.5628(2) 0.89809(11) 1.000 0.0164(4) d . . .
C15 C Uani 0.5134(3) 0.5730(2) 0.87416(13) 1.000 0.0234(5) d . . .
C16 C Uani 0.2373(3) 0.5315(2) 1.00574(12) 1.000 0.0248(5) d . . .
C17 C Uani 0.1797(3) 0.7267(2) 0.87320(13) 1.000 0.0225(4) d . . .
H2 H Uiso 0.57138 0.29114 0.37069 1.000 0.0280 c RU . .
H3 H Uiso 0.59217 0.27215 0.53738 1.000 0.0250 c RU . .
H6 H Uiso 0.01716 0.55365 0.39079 1.000 0.0250 c RU . .
H9 H Uiso -0.11140 0.60252 0.71879 1.000 0.0230 c RU . .
H10 H Uiso -0.12907 0.62342 0.55318 1.000 0.0260 c RU . .
H11A H Uiso 0.45974 0.16992 0.69225 1.000 0.0300 c RU . .
H11B H Uiso 0.63355 0.31053 0.69648 1.000 0.0300 c RU . .
H12A H Uiso 0.25688 0.24914 0.92434 1.000 0.0330 c RU . .
H12B H Uiso 0.17081 0.19044 0.82054 1.000 0.0330 c RU . .
H13 H Uiso -0.00182 0.42870 0.85553 1.000 0.0210 c RU . .
H15 H Uiso 0.55211 0.57669 0.80779 1.000 0.0280 c RU . .
H16A H Uiso 0.07978 0.52059 1.01883 1.000 0.0370 c RU . .
H16B H Uiso 0.29695 0.61931 1.04337 1.000 0.0370 c RU . .
H16C H Uiso 0.31346 0.43447 1.02405 1.000 0.0370 c RU . .
H17A H Uiso 0.21106 0.75100 0.80546 1.000 0.0340 c RU . .
H17B H Uiso 0.24949 0.80537 0.91493 1.000 0.0340 c RU . .
H17C H Uiso 0.02029 0.72794 0.88338 1.000 0.0340 c RU . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.7356(14) . . yes
O1 C11 1.414(2) . . yes
O1 C12 1.433(2) . . yes
O2 C15 1.204(2) . . yes
C1 C2 1.407(2) . . no
C1 C6 1.365(2) . . no
C2 C3 1.371(2) . . no
C3 C4 1.424(2) . . no
C4 C5 1.419(2) . . no
C4 C7 1.428(2) . . no
C5 C6 1.418(2) . . no
C5 C10 1.418(2) . . no
C7 C8 1.381(2) . . no
C7 C11 1.507(2) . . no
C8 C9 1.421(2) . . no
C8 C13 1.522(2) . . no
C9 C10 1.366(2) . . no
C12 C13 1.525(2) . . no
C13 C14 1.563(2) . . no
C14 C15 1.514(2) . . no
C14 C16 1.529(2) . . no
C14 C17 1.541(2) . . no
C2 H2 0.9500 . . no
C3 H3 0.9500 . . no
C6 H6 0.9500 . . no
C9 H9 0.9500 . . no
C10 H10 0.9500 . . no
C11 H11A 0.9900 . . no
C11 H11B 0.9900 . . no
C12 H12A 0.9900 . . no
C12 H12B 0.9900 . . no
C13 H13 1.0000 . . no
C15 H15 0.9500 . . no
C16 H16A 0.9800 . . no
C16 H16B 0.9800 . . no
C16 H16C 0.9800 . . no
C17 H17A 0.9800 . . no
C17 H17B 0.9800 . . no
C17 H17C 0.9800 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C12 111.87(13) . . . yes
Cl1 C1 C2 118.63(13) . . . yes
Cl1 C1 C6 119.81(13) . . . yes
C2 C1 C6 121.56(14) . . . no
C1 C2 C3 119.25(16) . . . no
C2 C3 C4 121.48(16) . . . no
C3 C4 C5 118.08(14) . . . no
C3 C4 C7 122.48(14) . . . no
C5 C4 C7 119.43(13) . . . no
C4 C5 C6 119.70(15) . . . no
C4 C5 C10 118.88(14) . . . no
C6 C5 C10 121.42(16) . . . no
C1 C6 C5 119.90(16) . . . no
C4 C7 C8 120.57(14) . . . no
C4 C7 C11 118.56(14) . . . no
C8 C7 C11 120.70(14) . . . no
C7 C8 C9 119.03(13) . . . no
C7 C8 C13 120.24(12) . . . no
C9 C8 C13 120.51(12) . . . no
C8 C9 C10 121.56(15) . . . no
C5 C10 C9 120.47(16) . . . no
O1 C11 C7 114.05(14) . . . yes
O1 C12 C13 108.14(13) . . . yes
C8 C13 C12 106.80(12) . . . no
C8 C13 C14 115.37(13) . . . no
C12 C13 C14 111.19(12) . . . no
C13 C14 C15 110.68(12) . . . no
C13 C14 C16 110.69(13) . . . no
C13 C14 C17 110.80(12) . . . no
C15 C14 C16 111.07(13) . . . no
C15 C14 C17 104.43(13) . . . no
C16 C14 C17 109.01(13) . . . no
O2 C15 C14 125.22(16) . . . yes
C1 C2 H2 120.00 . . . no
C3 C2 H2 120.00 . . . no
C2 C3 H3 119.00 . . . no
C4 C3 H3 119.00 . . . no
C1 C6 H6 120.00 . . . no
C5 C6 H6 120.00 . . . no
C8 C9 H9 119.00 . . . no
C10 C9 H9 119.00 . . . no
C5 C10 H10 120.00 . . . no
C9 C10 H10 120.00 . . . no
O1 C11 H11A 109.00 . . . no
O1 C11 H11B 109.00 . . . no
C7 C11 H11A 109.00 . . . no
C7 C11 H11B 109.00 . . . no
H11A C11 H11B 108.00 . . . no
O1 C12 H12A 110.00 . . . no
O1 C12 H12B 110.00 . . . no
C13 C12 H12A 110.00 . . . no
C13 C12 H12B 110.00 . . . no
H12A C12 H12B 108.00 . . . no
C8 C13 H13 108.00 . . . no
C12 C13 H13 108.00 . . . no
C14 C13 H13 108.00 . . . no
O2 C15 H15 117.00 . . . no
C14 C15 H15 117.00 . . . no
C14 C16 H16A 109.00 . . . no
C14 C16 H16B 109.00 . . . no
C14 C16 H16C 109.00 . . . no
H16A C16 H16B 109.00 . . . no
H16A C16 H16C 109.00 . . . no
H16B C16 H16C 109.00 . . . no
C14 C17 H17A 109.00 . . . no
C14 C17 H17B 109.00 . . . no
C14 C17 H17C 109.00 . . . no
H17A C17 H17B 109.00 . . . no
H17A C17 H17C 109.00 . . . no
H17B C17 H17C 109.00 . . . no

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
C12 O1 C11 C7 41.70(19) . . . . no
C11 O1 C12 C13 -70.93(17) . . . . no
Cl1 C1 C2 C3 -178.36(14) . . . . no
C6 C1 C2 C3 1.8(3) . . . . no
Cl1 C1 C6 C5 178.88(13) . . . . no
C2 C1 C6 C5 -1.3(3) . . . . no
C1 C2 C3 C4 -0.4(3) . . . . no
C2 C3 C4 C5 -1.4(2) . . . . no
C2 C3 C4 C7 177.33(16) . . . . no
C3 C4 C5 C6 1.9(2) . . . . no
C3 C4 C5 C10 -178.53(15) . . . . no
C7 C4 C5 C6 -176.87(15) . . . . no
C7 C4 C5 C10 2.7(2) . . . . no
C3 C4 C7 C8 178.78(15) . . . . no
C3 C4 C7 C11 -5.9(2) . . . . no
C5 C4 C7 C8 -2.5(2) . . . . no
C5 C4 C7 C11 172.82(15) . . . . no
C4 C5 C6 C1 -0.6(3) . . . . no
C10 C5 C6 C1 179.84(17) . . . . no
C4 C5 C10 C9 -1.2(3) . . . . no
C6 C5 C10 C9 178.37(17) . . . . no
C4 C7 C8 C9 0.7(2) . . . . no
C4 C7 C8 C13 175.25(13) . . . . no
C11 C7 C8 C9 -174.48(15) . . . . no
C11 C7 C8 C13 0.1(2) . . . . no
C4 C7 C11 O1 178.48(14) . . . . no
C8 C7 C11 O1 -6.2(2) . . . . no
C7 C8 C9 C10 0.8(2) . . . . no
C13 C8 C9 C10 -173.68(15) . . . . no
C7 C8 C13 C12 -26.20(18) . . . . no
C7 C8 C13 C14 97.94(16) . . . . no
C9 C8 C13 C12 148.26(14) . . . . no
C9 C8 C13 C14 -87.61(16) . . . . no
C8 C9 C10 C5 -0.6(3) . . . . no
O1 C12 C13 C8 59.96(15) . . . . no
O1 C12 C13 C14 -66.70(16) . . . . no
C8 C13 C14 C15 -61.48(16) . . . . no
C8 C13 C14 C16 174.93(12) . . . . no
C8 C13 C14 C17 53.89(15) . . . . no
C12 C13 C14 C15 60.33(17) . . . . no
C12 C13 C14 C16 -63.26(15) . . . . no
C12 C13 C14 C17 175.69(13) . . . . no
C13 C14 C15 O2 -132.39(18) . . . . no
C16 C14 C15 O2 -9.0(2) . . . . no
C17 C14 C15 O2 108.3(2) . . . . no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C11 H11A Cl1 0.9900 2.7700 3.3566(18) 119.00 2_646 yes
C12 H12A O2 0.9900 2.5100 3.424(2) 153.00 2_647 yes


####################################################################### 
# 
# 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_compound_8g
_database_code_depnum_ccdc_archive 'CCDC 2158147'
loop_
_audit_author_name
_audit_author_address
'Christian Jandl'
;Technical University of Munich
Germany
;
_audit_update_record             
;
2022-03-12 deposited with the CCDC.	2022-09-19 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 O2 S'
_chemical_formula_structural     ?
_chemical_formula_sum            'C19 H20 O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         312.41
_chemical_compound_source        'see text'

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'
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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_Int_Tables_number      19

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z

_cell_length_a                   6.4656(2)
_cell_length_b                   13.7036(5)
_cell_length_c                   17.0877(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1514.00(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9069
_cell_measurement_theta_min      2.3838
_cell_measurement_theta_max      28.2813
_cell_special_details            
;
;

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.165
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.095
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.219
_exptl_crystal_density_meas_temp ?

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2, Bruker, 2016'
_exptl_absorpt_correction_T_min  0.7233
_exptl_absorpt_correction_T_max  0.7457

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
Diffractometer operator             C. Jandl
scanspeed                           3-30 s per frame
dx                                  40 mm
2419 frames measured in 11 data sets
phi-scans with delta_phi         = 0.5
omega-scans with delta_omega     = 0.5
shutterless mode
;
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'IMS microsource'
_diffrn_radiation_monochromator  'Helios optic'

_diffrn_measurement_device       ' κ-geometry diffractometer '
_diffrn_measurement_device_type  ' Bruker D8 Venture '
_diffrn_measurement_method       ' phi- and omega-rotation '
_diffrn_detector                 ' Bruker Photon II CPAD '
_diffrn_detector_area_resol_mean 7.5

# number of measured reflections (redundant set)
_diffrn_reflns_number            66220
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             3615
# number of observed reflections (> n sig(I))
_reflns_number_gt                3533
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX III Control Software (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  
'SHELXL (Sheldrick, 2018), SHELXLE (Huebschle, 2011)'
_computing_molecular_graphics    'PLATON (Spek, 2011)'
_computing_publication_material  'PLATON (Spek, 2011), enCIFer (Allen, 2004)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'W=1/[Σ²(FO²)+(0.0303P)²+0.4484P] 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_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.031(15)

# Permitted for _chemical_absolute_configuration:
# Absolute configuration details
# rm   = Det. by chiral ref. mol. with known abs.conf
# ad   = Det. by anomalous dispersion
# rmad = Det. by 'rm' and 'ad'
# syn  = Det. with reference to synthesis
# unk  = Unknown/Arbitrary
_chemical_absolute_configuration ad

_refine_ls_number_reflns         3615
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0654
_refine_ls_wR_factor_gt          0.0648
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.037

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S Uani 0.42754(7) 0.76518(3) 0.43128(3) 1.000 0.0234(1) d . . .
O1 O Uani -0.04090(19) 0.57986(9) 0.34476(8) 1.000 0.0227(4) d . . .
O2 O Uani 0.10621(19) 0.41089(9) 0.23810(7) 1.000 0.0188(3) d . . .
C1 C Uani 0.2741(3) 0.74583(12) 0.34439(11) 1.000 0.0191(5) d . . .
C2 C Uani 0.3450(3) 0.65665(12) 0.29773(10) 1.000 0.0170(5) d . . .
C3 C Uani 0.3321(3) 0.55864(12) 0.34137(9) 1.000 0.0127(4) d . . .
C4 C Uani 0.4537(3) 0.56397(12) 0.41957(10) 1.000 0.0153(4) d . . .
C5 C Uani 0.3874(3) 0.64597(12) 0.47410(10) 1.000 0.0191(5) d . . .
C6 C Uani 0.1100(3) 0.53184(12) 0.36070(10) 1.000 0.0155(4) d . . .
C7 C Uani 0.4273(3) 0.47538(11) 0.28873(10) 1.000 0.0147(4) d . . .
C8 C Uani 0.2975(3) 0.45547(13) 0.21600(10) 1.000 0.0186(5) d . . .
C9 C Uani 0.1353(3) 0.31440(13) 0.26686(10) 1.000 0.0176(5) d . . .
C10 C Uani 0.3156(2) 0.30429(12) 0.32265(9) 1.000 0.0137(4) d . . .
C11 C Uani 0.4572(3) 0.37833(12) 0.33101(9) 1.000 0.0134(4) d . . .
C12 C Uani 0.3428(3) 0.21376(12) 0.36283(9) 1.000 0.0140(4) d . . .
C13 C Uani 0.5210(3) 0.20078(12) 0.41088(9) 1.000 0.0150(4) d . . .
C14 C Uani 0.6684(3) 0.27733(13) 0.41601(10) 1.000 0.0173(4) d . . .
C15 C Uani 0.6376(3) 0.36302(13) 0.37716(10) 1.000 0.0164(4) d . . .
C16 C Uani 0.2021(3) 0.13476(13) 0.35589(11) 1.000 0.0191(5) d . . .
C17 C Uani 0.2327(3) 0.04922(14) 0.39591(11) 1.000 0.0223(5) d . . .
C18 C Uani 0.4067(3) 0.03760(13) 0.44512(10) 1.000 0.0223(5) d . . .
C19 C Uani 0.5476(3) 0.11136(13) 0.45159(10) 1.000 0.0191(5) d . . .
H1A H Uiso 0.12752 0.73711 0.35963 1.000 0.0230 c RU . .
H1B H Uiso 0.28297 0.80444 0.31068 1.000 0.0230 c RU . .
H2A H Uiso 0.49008 0.66716 0.28125 1.000 0.0200 c RU . .
H2B H Uiso 0.25986 0.65206 0.24972 1.000 0.0200 c RU . .
H4A H Uiso 0.43734 0.50108 0.44740 1.000 0.0180 c RU . .
H4B H Uiso 0.60249 0.57208 0.40751 1.000 0.0180 c RU . .
H5A H Uiso 0.46687 0.64134 0.52347 1.000 0.0230 c RU . .
H5B H Uiso 0.23900 0.63805 0.48696 1.000 0.0230 c RU . .
H6 H Uiso 0.08777 0.47213 0.38767 1.000 0.0190 c RU . .
H7 H Uiso 0.56649 0.49801 0.27080 1.000 0.0180 c RU . .
H8A H Uiso 0.26986 0.51747 0.18816 1.000 0.0220 c RU . .
H8B H Uiso 0.37410 0.41173 0.18014 1.000 0.0220 c RU . .
H9A H Uiso 0.15737 0.27002 0.22191 1.000 0.0210 c RU . .
H9B H Uiso 0.00754 0.29333 0.29393 1.000 0.0210 c RU . .
H14 H Uiso 0.78947 0.26877 0.44676 1.000 0.0210 c RU . .
H15 H Uiso 0.73825 0.41332 0.38095 1.000 0.0200 c RU . .
H16 H Uiso 0.08452 0.14125 0.32294 1.000 0.0230 c RU . .
H17 H Uiso 0.13617 -0.00263 0.39052 1.000 0.0270 c RU . .
H18 H Uiso 0.42547 -0.02129 0.47358 1.000 0.0270 c RU . .
H19 H Uiso 0.66566 0.10268 0.48395 1.000 0.0230 c RU . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.805(2) . . yes
S1 C5 1.8087(17) . . yes
O1 C6 1.208(2) . . yes
O2 C8 1.430(2) . . yes
O2 C9 1.423(2) . . yes
C1 C2 1.530(2) . . no
C2 C3 1.539(2) . . no
C3 C4 1.552(2) . . no
C3 C6 1.519(3) . . no
C3 C7 1.578(2) . . no
C4 C5 1.521(2) . . no
C7 C8 1.524(3) . . no
C7 C11 1.526(2) . . no
C9 C10 1.512(2) . . no
C10 C11 1.374(2) . . no
C10 C12 1.429(2) . . no
C11 C15 1.424(3) . . no
C12 C13 1.426(3) . . no
C12 C16 1.419(3) . . no
C13 C14 1.420(3) . . no
C13 C19 1.420(2) . . no
C14 C15 1.364(3) . . no
C16 C17 1.371(3) . . no
C17 C18 1.414(3) . . no
C18 C19 1.365(3) . . no
C1 H1A 0.9900 . . no
C1 H1B 0.9900 . . no
C2 H2A 0.9900 . . no
C2 H2B 0.9900 . . no
C4 H4A 0.9900 . . no
C4 H4B 0.9900 . . no
C5 H5A 0.9900 . . no
C5 H5B 0.9900 . . no
C6 H6 0.9500 . . no
C7 H7 1.0000 . . no
C8 H8A 0.9900 . . no
C8 H8B 0.9900 . . no
C9 H9A 0.9900 . . no
C9 H9B 0.9900 . . no
C14 H14 0.9500 . . no
C15 H15 0.9500 . . no
C16 H16 0.9500 . . no
C17 H17 0.9500 . . no
C18 H18 0.9500 . . no
C19 H19 0.9500 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C5 96.96(8) . . . yes
C8 O2 C9 111.95(13) . . . yes
S1 C1 C2 112.42(13) . . . yes
C1 C2 C3 115.38(14) . . . no
C2 C3 C4 110.41(14) . . . no
C2 C3 C6 111.58(15) . . . no
C2 C3 C7 109.50(13) . . . no
C4 C3 C6 107.65(14) . . . no
C4 C3 C7 109.10(14) . . . no
C6 C3 C7 108.54(14) . . . no
C3 C4 C5 114.79(15) . . . no
S1 C5 C4 112.27(12) . . . yes
O1 C6 C3 125.66(15) . . . yes
C3 C7 C8 112.30(15) . . . no
C3 C7 C11 114.19(14) . . . no
C8 C7 C11 107.45(13) . . . no
O2 C8 C7 109.71(14) . . . yes
O2 C9 C10 113.87(14) . . . yes
C9 C10 C11 120.76(15) . . . no
C9 C10 C12 118.51(14) . . . no
C11 C10 C12 120.61(14) . . . no
C7 C11 C10 120.66(16) . . . no
C7 C11 C15 119.64(16) . . . no
C10 C11 C15 119.65(15) . . . no
C10 C12 C13 118.98(15) . . . no
C10 C12 C16 122.91(16) . . . no
C13 C12 C16 118.10(15) . . . no
C12 C13 C14 119.06(15) . . . no
C12 C13 C19 119.19(16) . . . no
C14 C13 C19 121.75(17) . . . no
C13 C14 C15 120.54(17) . . . no
C11 C15 C14 121.09(17) . . . no
C12 C16 C17 121.19(17) . . . no
C16 C17 C18 120.51(17) . . . no
C17 C18 C19 119.73(17) . . . no
C13 C19 C18 121.24(17) . . . no
S1 C1 H1A 109.00 . . . no
S1 C1 H1B 109.00 . . . no
C2 C1 H1A 109.00 . . . no
C2 C1 H1B 109.00 . . . no
H1A C1 H1B 108.00 . . . no
C1 C2 H2A 108.00 . . . no
C1 C2 H2B 108.00 . . . no
C3 C2 H2A 108.00 . . . no
C3 C2 H2B 108.00 . . . no
H2A C2 H2B 107.00 . . . no
C3 C4 H4A 109.00 . . . no
C3 C4 H4B 109.00 . . . no
C5 C4 H4A 109.00 . . . no
C5 C4 H4B 109.00 . . . no
H4A C4 H4B 108.00 . . . no
S1 C5 H5A 109.00 . . . no
S1 C5 H5B 109.00 . . . no
C4 C5 H5A 109.00 . . . no
C4 C5 H5B 109.00 . . . no
H5A C5 H5B 108.00 . . . no
O1 C6 H6 117.00 . . . no
C3 C6 H6 117.00 . . . no
C3 C7 H7 108.00 . . . no
C8 C7 H7 108.00 . . . no
C11 C7 H7 108.00 . . . no
O2 C8 H8A 110.00 . . . no
O2 C8 H8B 110.00 . . . no
C7 C8 H8A 110.00 . . . no
C7 C8 H8B 110.00 . . . no
H8A C8 H8B 108.00 . . . no
O2 C9 H9A 109.00 . . . no
O2 C9 H9B 109.00 . . . no
C10 C9 H9A 109.00 . . . no
C10 C9 H9B 109.00 . . . no
H9A C9 H9B 108.00 . . . no
C13 C14 H14 120.00 . . . no
C15 C14 H14 120.00 . . . no
C11 C15 H15 119.00 . . . no
C14 C15 H15 119.00 . . . no
C12 C16 H16 119.00 . . . no
C17 C16 H16 119.00 . . . no
C16 C17 H17 120.00 . . . no
C18 C17 H17 120.00 . . . no
C17 C18 H18 120.00 . . . no
C19 C18 H18 120.00 . . . no
C13 C19 H19 119.00 . . . no
C18 C19 H19 119.00 . . . no

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 S1 C1 C2 -55.93(14) . . . . no
C1 S1 C5 C4 56.78(15) . . . . no
C9 O2 C8 C7 -68.92(17) . . . . no
C8 O2 C9 C10 43.79(18) . . . . no
S1 C1 C2 C3 61.06(19) . . . . no
C1 C2 C3 C4 -55.1(2) . . . . no
C1 C2 C3 C6 64.54(19) . . . . no
C1 C2 C3 C7 -175.28(15) . . . . no
C2 C3 C4 C5 55.8(2) . . . . no
C6 C3 C4 C5 -66.27(18) . . . . no
C7 C3 C4 C5 176.13(14) . . . . no
C2 C3 C6 O1 -0.1(2) . . . . no
C4 C3 C6 O1 121.19(18) . . . . no
C7 C3 C6 O1 -120.86(18) . . . . no
C2 C3 C7 C8 -67.36(19) . . . . no
C2 C3 C7 C11 169.99(15) . . . . no
C4 C3 C7 C8 171.70(14) . . . . no
C4 C3 C7 C11 49.1(2) . . . . no
C6 C3 C7 C8 54.67(18) . . . . no
C6 C3 C7 C11 -67.98(19) . . . . no
C3 C4 C5 S1 -62.19(18) . . . . no
C3 C7 C8 O2 -69.36(17) . . . . no
C11 C7 C8 O2 57.02(18) . . . . no
C3 C7 C11 C10 99.12(18) . . . . no
C3 C7 C11 C15 -83.3(2) . . . . no
C8 C7 C11 C10 -26.1(2) . . . . no
C8 C7 C11 C15 151.43(16) . . . . no
O2 C9 C10 C11 -11.8(2) . . . . no
O2 C9 C10 C12 172.03(14) . . . . no
C9 C10 C11 C7 4.5(2) . . . . no
C9 C10 C11 C15 -173.07(15) . . . . no
C12 C10 C11 C7 -179.43(15) . . . . no
C12 C10 C11 C15 3.0(2) . . . . no
C9 C10 C12 C13 175.20(15) . . . . no
C9 C10 C12 C16 -3.4(2) . . . . no
C11 C10 C12 C13 -1.0(2) . . . . no
C11 C10 C12 C16 -179.60(16) . . . . no
C7 C11 C15 C14 179.64(16) . . . . no
C10 C11 C15 C14 -2.8(3) . . . . no
C10 C12 C13 C14 -1.4(2) . . . . no
C10 C12 C13 C19 179.33(15) . . . . no
C16 C12 C13 C14 177.32(16) . . . . no
C16 C12 C13 C19 -2.0(2) . . . . no
C10 C12 C16 C17 -179.48(17) . . . . no
C13 C12 C16 C17 1.9(3) . . . . no
C12 C13 C14 C15 1.7(3) . . . . no
C19 C13 C14 C15 -179.08(17) . . . . no
C12 C13 C19 C18 0.5(3) . . . . no
C14 C13 C19 C18 -178.82(17) . . . . no
C13 C14 C15 C11 0.4(3) . . . . no
C12 C16 C17 C18 -0.2(3) . . . . no
C16 C17 C18 C19 -1.4(3) . . . . no
C17 C18 C19 C13 1.2(3) . . . . no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C1 H1A O1 0.9900 2.4300 3.053(2) 121.00 . yes
C4 H4B O1 0.9900 2.5500 3.516(2) 167.00 1_655 yes
C5 H5B S1 0.9900 2.7900 3.5968(19) 139.00 3_466 yes


