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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1936853'
loop_
_audit_author_name
_audit_author_address
'Chiral allyl alcohol'
;Nankai University
China
;
_audit_update_record             
;
2019-06-27 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H27 N O5 S'
_chemical_formula_weight         453.53

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'

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

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

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

_cell_length_a                   9.954(2)
_cell_length_b                   14.826(3)
_cell_length_c                   15.404(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.53(3)
_cell_angle_gamma                90
_cell_volume                     2266.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    6946
_cell_measurement_theta_min      1.9093
_cell_measurement_theta_max      28.0187

_exptl_crystal_description       'acicular crystal'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.8206
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            24519
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.909
_diffrn_reflns_theta_max         27.909
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             10608
_reflns_number_gt                8829
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_max     0.960
_reflns_Friedel_fraction_full    0.984

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0643P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2746 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_chemical_absolute_configuration S,S
_refine_ls_number_reflns         10608
_refine_ls_number_parameters     583
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1169
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.55118(8) -0.03009(5) 1.12284(5) 0.02329(18) Uani 1 1 d . . . . .
S2 S 1.07012(9) 0.50761(5) 1.10819(5) 0.02488(19) Uani 1 1 d . . . . .
O1 O 0.6483(2) -0.07362(16) 1.07382(15) 0.0285(6) Uani 1 1 d . . . . .
O2 O 0.4650(3) -0.08173(16) 1.17381(15) 0.0295(6) Uani 1 1 d . . . . .
O3 O 0.6293(2) 0.26594(16) 0.73202(14) 0.0245(5) Uani 1 1 d . . . . .
H3 H 0.635665 0.306628 0.770067 0.037 Uiso 1 1 calc R U . . .
O4 O 0.4633(3) 0.34859(17) 0.58489(15) 0.0319(6) Uani 1 1 d . . . . .
O5 O 0.5651(3) 0.2511(2) 0.50106(16) 0.0418(7) Uani 1 1 d . . . . .
O6 O 1.1694(3) 0.54585(17) 1.05670(15) 0.0315(6) Uani 1 1 d . . . . .
O7 O 0.9869(3) 0.56361(16) 1.15669(15) 0.0294(5) Uani 1 1 d . . . . .
O8 O 0.8535(2) 0.26555(18) 0.63386(14) 0.0288(5) Uani 1 1 d . . . . .
H8 H 0.776829 0.268953 0.652834 0.043 Uiso 1 1 calc R U . . .
O9 O 1.0899(3) 0.1961(2) 0.51179(17) 0.0490(8) Uani 1 1 d . . . . .
O10 O 1.0495(3) 0.08994(18) 0.61001(16) 0.0378(6) Uani 1 1 d . . . . .
N1 N 0.4511(3) 0.02666(18) 1.05107(17) 0.0221(6) Uani 1 1 d . . . . .
N2 N 0.9674(3) 0.44953(18) 1.03887(16) 0.0220(6) Uani 1 1 d . . . . .
C1 C 0.6308(3) 0.0527(2) 1.1894(2) 0.0238(7) Uani 1 1 d . . . . .
C2 C 0.5872(4) 0.0677(3) 1.2721(2) 0.0295(8) Uani 1 1 d . . . . .
H2 H 0.516136 0.032605 1.292242 0.035 Uiso 1 1 calc R U . . .
C3 C 0.6484(4) 0.1343(3) 1.3245(2) 0.0316(8) Uani 1 1 d . . . . .
H3A H 0.619973 0.144091 1.381161 0.038 Uiso 1 1 calc R U . . .
C4 C 0.7508(4) 0.1868(3) 1.2951(2) 0.0324(8) Uani 1 1 d . . . . .
C5 C 0.7933(4) 0.1709(3) 1.2133(2) 0.0316(8) Uani 1 1 d . . . . .
H5 H 0.863858 0.206481 1.193191 0.038 Uiso 1 1 calc R U . . .
C6 C 0.7351(4) 0.1039(2) 1.1598(2) 0.0279(8) Uani 1 1 d . . . . .
H6 H 0.765848 0.093227 1.103904 0.033 Uiso 1 1 calc R U . . .
C7 C 0.8140(5) 0.2610(3) 1.3519(3) 0.0487(11) Uani 1 1 d . . . . .
H7A H 0.897939 0.239016 1.382178 0.073 Uiso 1 1 calc R U . . .
H7B H 0.751562 0.279216 1.394808 0.073 Uiso 1 1 calc R U . . .
H7C H 0.833489 0.312962 1.315611 0.073 Uiso 1 1 calc R U . . .
C8 C 0.3291(3) 0.0695(2) 1.0678(2) 0.0206(6) Uani 1 1 d . . . . .
C9 C 0.2434(3) 0.0581(2) 1.1337(2) 0.0247(7) Uani 1 1 d . . . . .
H9 H 0.263246 0.016109 1.179451 0.030 Uiso 1 1 calc R U . . .
C10 C 0.1283(4) 0.1101(2) 1.1301(2) 0.0272(8) Uani 1 1 d . . . . .
H10 H 0.068363 0.104073 1.174766 0.033 Uiso 1 1 calc R U . . .
C11 C 0.0975(3) 0.1712(2) 1.0628(2) 0.0269(7) Uani 1 1 d . . . . .
H11 H 0.016831 0.205565 1.062090 0.032 Uiso 1 1 calc R U . . .
C12 C 0.1827(3) 0.1825(2) 0.9970(2) 0.0234(7) Uani 1 1 d . . . . .
H12 H 0.161001 0.223778 0.950900 0.028 Uiso 1 1 calc R U . . .
C13 C 0.3012(3) 0.1322(2) 0.9997(2) 0.0204(7) Uani 1 1 d . . . . .
C14 C 0.4089(3) 0.1271(2) 0.9417(2) 0.0197(7) Uani 1 1 d . . . . .
C15 C 0.4981(3) 0.0652(2) 0.97623(19) 0.0219(7) Uani 1 1 d . . . . .
H15 H 0.580722 0.050133 0.952911 0.026 Uiso 1 1 calc R U . . .
C16 C 0.4168(3) 0.1815(2) 0.86292(19) 0.0209(6) Uani 1 1 d . . . . .
H16 H 0.372256 0.238231 0.862196 0.025 Uiso 1 1 calc R U . . .
C17 C 0.4793(3) 0.1606(2) 0.7918(2) 0.0215(7) Uani 1 1 d . . . . .
C18 C 0.5492(4) 0.0729(2) 0.7771(2) 0.0278(7) Uani 1 1 d . . . . .
H18A H 0.519852 0.027373 0.818670 0.033 Uiso 1 1 calc R U . . .
H18B H 0.647699 0.081194 0.788632 0.033 Uiso 1 1 calc R U . . .
C19 C 0.5188(4) 0.0383(2) 0.6842(2) 0.0353(9) Uani 1 1 d . . . . .
H19A H 0.422082 0.022455 0.674749 0.042 Uiso 1 1 calc R U . . .
H19B H 0.572179 -0.016867 0.675461 0.042 Uiso 1 1 calc R U . . .
C20 C 0.5534(4) 0.1104(2) 0.6182(2) 0.0314(8) Uani 1 1 d . . . . .
H20A H 0.650805 0.124580 0.626245 0.038 Uiso 1 1 calc R U . . .
H20B H 0.533651 0.087114 0.558368 0.038 Uiso 1 1 calc R U . . .
C21 C 0.4721(3) 0.1957(2) 0.63015(19) 0.0234(7) Uani 1 1 d . . . . .
H21 H 0.374475 0.180356 0.618581 0.028 Uiso 1 1 calc R U . . .
C22 C 0.4933(3) 0.2322(2) 0.72333(19) 0.0195(6) Uani 1 1 d . . . . .
H22 H 0.428640 0.282459 0.731585 0.023 Uiso 1 1 calc R U . . .
C23 C 0.5067(3) 0.2663(2) 0.5645(2) 0.0266(7) Uani 1 1 d . . . . .
C24 C 0.5003(4) 0.4219(3) 0.5297(3) 0.0395(10) Uani 1 1 d . . . . .
H24A H 0.438718 0.473416 0.536279 0.047 Uiso 1 1 calc R U . . .
H24B H 0.490289 0.402223 0.468109 0.047 Uiso 1 1 calc R U . . .
C25 C 0.6431(4) 0.4516(3) 0.5524(3) 0.0495(11) Uani 1 1 d . . . . .
H25A H 0.655465 0.465483 0.614755 0.074 Uiso 1 1 calc R U . . .
H25B H 0.661914 0.505587 0.518722 0.074 Uiso 1 1 calc R U . . .
H25C H 0.704931 0.403203 0.538642 0.074 Uiso 1 1 calc R U . . .
C26 C 1.1468(4) 0.4261(2) 1.1785(2) 0.0252(7) Uani 1 1 d . . . . .
C27 C 1.2473(4) 0.3712(2) 1.1509(2) 0.0287(8) Uani 1 1 d . . . . .
H27 H 1.280313 0.380174 1.095363 0.034 Uiso 1 1 calc R U . . .
C28 C 1.2994(4) 0.3029(3) 1.2050(2) 0.0315(8) Uani 1 1 d . . . . .
H28 H 1.368239 0.264998 1.186051 0.038 Uiso 1 1 calc R U . . .
C29 C 1.2521(4) 0.2890(3) 1.2869(2) 0.0304(8) Uani 1 1 d . . . . .
C30 C 1.1540(4) 0.3468(3) 1.3136(2) 0.0336(8) Uani 1 1 d . . . . .
H30 H 1.123184 0.339564 1.369981 0.040 Uiso 1 1 calc R U . . .
C31 C 1.1001(4) 0.4147(3) 1.2604(2) 0.0293(8) Uani 1 1 d . . . . .
H31 H 1.031892 0.453085 1.279488 0.035 Uiso 1 1 calc R U . . .
C32 C 1.3044(4) 0.2127(3) 1.3434(3) 0.0442(11) Uani 1 1 d . . . . .
H32A H 1.396429 0.226318 1.367151 0.066 Uiso 1 1 calc R U . . .
H32B H 1.304644 0.157253 1.308815 0.066 Uiso 1 1 calc R U . . .
H32C H 1.246429 0.204541 1.391369 0.066 Uiso 1 1 calc R U . . .
C33 C 0.8466(3) 0.4070(2) 1.0586(2) 0.0209(7) Uani 1 1 d . . . . .
C34 C 0.7644(4) 0.4219(2) 1.1263(2) 0.0256(7) Uani 1 1 d . . . . .
H34 H 0.786283 0.465732 1.170090 0.031 Uiso 1 1 calc R U . . .
C35 C 0.6495(4) 0.3698(2) 1.1265(2) 0.0294(8) Uani 1 1 d . . . . .
H35 H 0.592129 0.377362 1.172430 0.035 Uiso 1 1 calc R U . . .
C36 C 0.6145(4) 0.3061(3) 1.0613(2) 0.0295(8) Uani 1 1 d . . . . .
H36 H 0.533961 0.272067 1.063202 0.035 Uiso 1 1 calc R U . . .
C37 C 0.6963(3) 0.2927(2) 0.9944(2) 0.0249(7) Uani 1 1 d . . . . .
H37 H 0.672695 0.249917 0.949896 0.030 Uiso 1 1 calc R U . . .
C38 C 0.8143(3) 0.3430(2) 0.9931(2) 0.0199(7) Uani 1 1 d . . . . .
C39 C 0.9194(3) 0.3457(2) 0.9329(2) 0.0209(7) Uani 1 1 d . . . . .
C40 C 1.0113(4) 0.4083(2) 0.9638(2) 0.0227(7) Uani 1 1 d . . . . .
H40 H 1.092768 0.422165 0.938443 0.027 Uiso 1 1 calc R U . . .
C41 C 0.9214(3) 0.2892(2) 0.85479(19) 0.0205(6) Uani 1 1 d . . . . .
H41 H 0.894786 0.228242 0.861438 0.025 Uiso 1 1 calc R U . . .
C42 C 0.9555(3) 0.3119(2) 0.7759(2) 0.0223(7) Uani 1 1 d . . . . .
C43 C 0.9987(4) 0.4043(2) 0.7484(2) 0.0283(8) Uani 1 1 d . . . . .
H43A H 1.004810 0.445253 0.799326 0.034 Uiso 1 1 calc R U . . .
H43B H 0.930848 0.429120 0.704306 0.034 Uiso 1 1 calc R U . . .
C44 C 1.1350(4) 0.3988(3) 0.7104(2) 0.0352(9) Uani 1 1 d . . . . .
H44A H 1.204282 0.379142 0.756159 0.042 Uiso 1 1 calc R U . . .
H44B H 1.160651 0.459197 0.689915 0.042 Uiso 1 1 calc R U . . .
C45 C 1.1299(4) 0.3320(3) 0.6343(2) 0.0333(8) Uani 1 1 d . . . . .
H45A H 1.065331 0.354080 0.586813 0.040 Uiso 1 1 calc R U . . .
H45B H 1.219911 0.328180 0.611471 0.040 Uiso 1 1 calc R U . . .
C46 C 1.0868(3) 0.2385(2) 0.6630(2) 0.0267(7) Uani 1 1 d . . . . .
H46 H 1.156668 0.214769 0.707390 0.032 Uiso 1 1 calc R U . . .
C47 C 0.9508(3) 0.2421(2) 0.7036(2) 0.0227(7) Uani 1 1 d . . . . .
H47 H 0.929183 0.181519 0.727315 0.027 Uiso 1 1 calc R U . . .
C48 C 1.0764(4) 0.1751(3) 0.5855(2) 0.0315(8) Uani 1 1 d . . . . .
C49 C 1.0127(4) 0.0271(3) 0.5396(3) 0.0413(10) Uani 1 1 d . . . . .
H49A H 1.037147 -0.035067 0.558332 0.050 Uiso 1 1 calc R U . . .
H49B H 1.062689 0.041999 0.488439 0.050 Uiso 1 1 calc R U . . .
C50 C 0.8648(4) 0.0325(3) 0.5155(3) 0.0488(11) Uani 1 1 d . . . . .
H50A H 0.815736 0.017658 0.566284 0.073 Uiso 1 1 calc R U . . .
H50B H 0.840238 -0.010417 0.468472 0.073 Uiso 1 1 calc R U . . .
H50C H 0.841367 0.093740 0.495774 0.073 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.427(2) . ?
S1 O2 1.430(2) . ?
S1 N1 1.658(3) . ?
S1 C1 1.749(4) . ?
S2 O7 1.425(2) . ?
S2 O6 1.432(2) . ?
S2 N2 1.660(3) . ?
S2 C26 1.757(4) . ?
O3 C22 1.439(4) . ?
O3 H3 0.8400 . ?
O4 C23 1.340(4) . ?
O4 C24 1.445(4) . ?
O5 C23 1.197(4) . ?
O8 C47 1.431(4) . ?
O8 H8 0.8400 . ?
O9 C48 1.194(4) . ?
O10 C48 1.351(5) . ?
O10 C49 1.455(4) . ?
N1 C15 1.400(4) . ?
N1 C8 1.412(4) . ?
N2 C40 1.408(4) . ?
N2 C33 1.412(4) . ?
C1 C6 1.392(5) . ?
C1 C2 1.395(4) . ?
C2 C3 1.386(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.381(5) . ?
C4 C7 1.512(6) . ?
C5 C6 1.387(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.387(4) . ?
C8 C13 1.412(4) . ?
C9 C10 1.378(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.382(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.451(4) . ?
C14 C15 1.356(5) . ?
C14 C16 1.465(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.339(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.501(4) . ?
C17 C22 1.509(4) . ?
C18 C19 1.529(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.533(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.521(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C23 1.513(4) . ?
C21 C22 1.532(4) . ?
C21 H21 1.0000 . ?
C22 H22 1.0000 . ?
C24 C25 1.503(6) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.383(5) . ?
C26 C31 1.389(4) . ?
C27 C28 1.385(5) . ?
C27 H27 0.9500 . ?
C28 C29 1.397(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(5) . ?
C29 C32 1.496(5) . ?
C30 C31 1.380(5) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.392(4) . ?
C33 C38 1.405(4) . ?
C34 C35 1.380(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.403(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.377(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.392(5) . ?
C37 H37 0.9500 . ?
C38 C39 1.453(4) . ?
C39 C40 1.363(5) . ?
C39 C41 1.467(4) . ?
C40 H40 0.9500 . ?
C41 C42 1.331(4) . ?
C41 H41 0.9500 . ?
C42 C43 1.506(4) . ?
C42 C47 1.518(4) . ?
C43 C44 1.522(5) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C45 1.532(5) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C46 1.528(5) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 C48 1.516(5) . ?
C46 C47 1.536(4) . ?
C46 H46 1.0000 . ?
C47 H47 1.0000 . ?
C49 C50 1.492(6) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 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
O1 S1 O2 120.62(16) . . ?
O1 S1 N1 105.86(13) . . ?
O2 S1 N1 106.45(14) . . ?
O1 S1 C1 109.45(16) . . ?
O2 S1 C1 108.49(15) . . ?
N1 S1 C1 104.81(15) . . ?
O7 S2 O6 120.99(15) . . ?
O7 S2 N2 106.57(15) . . ?
O6 S2 N2 105.45(14) . . ?
O7 S2 C26 108.66(15) . . ?
O6 S2 C26 109.18(16) . . ?
N2 S2 C26 104.79(15) . . ?
C22 O3 H3 109.5 . . ?
C23 O4 C24 116.4(3) . . ?
C47 O8 H8 109.5 . . ?
C48 O10 C49 115.7(3) . . ?
C15 N1 C8 108.3(3) . . ?
C15 N1 S1 122.3(2) . . ?
C8 N1 S1 125.9(2) . . ?
C40 N2 C33 108.0(3) . . ?
C40 N2 S2 122.5(2) . . ?
C33 N2 S2 125.8(2) . . ?
C6 C1 C2 120.4(3) . . ?
C6 C1 S1 120.4(2) . . ?
C2 C1 S1 119.2(3) . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C5 C4 C3 119.2(4) . . ?
C5 C4 C7 120.6(3) . . ?
C3 C4 C7 120.2(3) . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 121.8(3) . . ?
C9 C8 N1 131.8(3) . . ?
C13 C8 N1 106.4(3) . . ?
C10 C9 C8 117.4(3) . . ?
C10 C9 H9 121.3 . . ?
C8 C9 H9 121.3 . . ?
C9 C10 C11 121.8(3) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 118.7(3) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C12 C13 C8 119.4(3) . . ?
C12 C13 C14 132.4(3) . . ?
C8 C13 C14 108.2(3) . . ?
C15 C14 C13 106.6(3) . . ?
C15 C14 C16 128.4(3) . . ?
C13 C14 C16 124.9(3) . . ?
C14 C15 N1 110.4(3) . . ?
C14 C15 H15 124.8 . . ?
N1 C15 H15 124.8 . . ?
C17 C16 C14 127.6(3) . . ?
C17 C16 H16 116.2 . . ?
C14 C16 H16 116.2 . . ?
C16 C17 C18 125.1(3) . . ?
C16 C17 C22 118.9(3) . . ?
C18 C17 C22 115.8(3) . . ?
C17 C18 C19 111.8(3) . . ?
C17 C18 H18A 109.3 . . ?
C19 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
C19 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 C20 110.3(3) . . ?
C18 C19 H19A 109.6 . . ?
C20 C19 H19A 109.6 . . ?
C18 C19 H19B 109.6 . . ?
C20 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
C21 C20 C19 110.5(3) . . ?
C21 C20 H20A 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C23 C21 C20 110.0(3) . . ?
C23 C21 C22 111.1(3) . . ?
C20 C21 C22 111.7(3) . . ?
C23 C21 H21 107.9 . . ?
C20 C21 H21 107.9 . . ?
C22 C21 H21 107.9 . . ?
O3 C22 C17 108.5(3) . . ?
O3 C22 C21 105.6(2) . . ?
C17 C22 C21 113.1(3) . . ?
O3 C22 H22 109.8 . . ?
C17 C22 H22 109.8 . . ?
C21 C22 H22 109.8 . . ?
O5 C23 O4 123.3(3) . . ?
O5 C23 C21 124.5(3) . . ?
O4 C23 C21 112.2(3) . . ?
O4 C24 C25 111.3(3) . . ?
O4 C24 H24A 109.4 . . ?
C25 C24 H24A 109.4 . . ?
O4 C24 H24B 109.4 . . ?
C25 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C31 120.7(3) . . ?
C27 C26 S2 120.4(2) . . ?
C31 C26 S2 118.9(3) . . ?
C26 C27 C28 119.4(3) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C27 C28 C29 121.0(3) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 H28 119.5 . . ?
C30 C29 C28 118.2(4) . . ?
C30 C29 C32 121.1(3) . . ?
C28 C29 C32 120.7(3) . . ?
C31 C30 C29 121.7(3) . . ?
C31 C30 H30 119.2 . . ?
C29 C30 H30 119.2 . . ?
C30 C31 C26 119.1(3) . . ?
C30 C31 H31 120.5 . . ?
C26 C31 H31 120.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 C38 122.0(3) . . ?
C34 C33 N2 130.7(3) . . ?
C38 C33 N2 107.3(3) . . ?
C35 C34 C33 116.7(3) . . ?
C35 C34 H34 121.6 . . ?
C33 C34 H34 121.6 . . ?
C34 C35 C36 122.2(3) . . ?
C34 C35 H35 118.9 . . ?
C36 C35 H35 118.9 . . ?
C37 C36 C35 120.3(3) . . ?
C37 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
C36 C37 C38 118.9(3) . . ?
C36 C37 H37 120.6 . . ?
C38 C37 H37 120.6 . . ?
C37 C38 C33 119.8(3) . . ?
C37 C38 C39 132.4(3) . . ?
C33 C38 C39 107.8(3) . . ?
C40 C39 C38 107.0(3) . . ?
C40 C39 C41 128.6(3) . . ?
C38 C39 C41 124.4(3) . . ?
C39 C40 N2 109.8(3) . . ?
C39 C40 H40 125.1 . . ?
N2 C40 H40 125.1 . . ?
C42 C41 C39 128.7(3) . . ?
C42 C41 H41 115.6 . . ?
C39 C41 H41 115.6 . . ?
C41 C42 C43 125.8(3) . . ?
C41 C42 C47 120.1(3) . . ?
C43 C42 C47 114.0(3) . . ?
C42 C43 C44 110.0(3) . . ?
C42 C43 H43A 109.7 . . ?
C44 C43 H43A 109.7 . . ?
C42 C43 H43B 109.7 . . ?
C44 C43 H43B 109.7 . . ?
H43A C43 H43B 108.2 . . ?
C43 C44 C45 110.6(3) . . ?
C43 C44 H44A 109.5 . . ?
C45 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
C45 C44 H44B 109.5 . . ?
H44A C44 H44B 108.1 . . ?
C46 C45 C44 111.0(3) . . ?
C46 C45 H45A 109.4 . . ?
C44 C45 H45A 109.4 . . ?
C46 C45 H45B 109.4 . . ?
C44 C45 H45B 109.4 . . ?
H45A C45 H45B 108.0 . . ?
C48 C46 C45 109.7(3) . . ?
C48 C46 C47 109.6(3) . . ?
C45 C46 C47 111.2(3) . . ?
C48 C46 H46 108.7 . . ?
C45 C46 H46 108.7 . . ?
C47 C46 H46 108.7 . . ?
O8 C47 C42 111.4(3) . . ?
O8 C47 C46 105.6(2) . . ?
C42 C47 C46 110.2(3) . . ?
O8 C47 H47 109.9 . . ?
C42 C47 H47 109.9 . . ?
C46 C47 H47 109.9 . . ?
O9 C48 O10 123.3(3) . . ?
O9 C48 C46 125.5(4) . . ?
O10 C48 C46 111.2(3) . . ?
O10 C49 C50 109.7(3) . . ?
O10 C49 H49A 109.7 . . ?
C50 C49 H49A 109.7 . . ?
O10 C49 H49B 109.7 . . ?
C50 C49 H49B 109.7 . . ?
H49A C49 H49B 108.2 . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N1 C15 -33.1(3) . . . . ?
O2 S1 N1 C15 -162.6(3) . . . . ?
C1 S1 N1 C15 82.6(3) . . . . ?
O1 S1 N1 C8 170.4(3) . . . . ?
O2 S1 N1 C8 40.9(3) . . . . ?
C1 S1 N1 C8 -74.0(3) . . . . ?
O7 S2 N2 C40 160.4(2) . . . . ?
O6 S2 N2 C40 30.6(3) . . . . ?
C26 S2 N2 C40 -84.6(3) . . . . ?
O7 S2 N2 C33 -43.9(3) . . . . ?
O6 S2 N2 C33 -173.7(3) . . . . ?
C26 S2 N2 C33 71.1(3) . . . . ?
O1 S1 C1 C6 37.1(3) . . . . ?
O2 S1 C1 C6 170.5(3) . . . . ?
N1 S1 C1 C6 -76.1(3) . . . . ?
O1 S1 C1 C2 -143.9(3) . . . . ?
O2 S1 C1 C2 -10.5(3) . . . . ?
N1 S1 C1 C2 102.9(3) . . . . ?
C6 C1 C2 C3 0.1(5) . . . . ?
S1 C1 C2 C3 -178.9(3) . . . . ?
C1 C2 C3 C4 1.0(6) . . . . ?
C2 C3 C4 C5 -1.3(6) . . . . ?
C2 C3 C4 C7 178.3(4) . . . . ?
C3 C4 C5 C6 0.5(6) . . . . ?
C7 C4 C5 C6 -179.1(4) . . . . ?
C4 C5 C6 C1 0.6(6) . . . . ?
C2 C1 C6 C5 -0.9(5) . . . . ?
S1 C1 C6 C5 178.1(3) . . . . ?
C15 N1 C8 C9 -178.9(3) . . . . ?
S1 N1 C8 C9 -19.6(5) . . . . ?
C15 N1 C8 C13 2.1(3) . . . . ?
S1 N1 C8 C13 161.4(2) . . . . ?
C13 C8 C9 C10 0.4(5) . . . . ?
N1 C8 C9 C10 -178.4(3) . . . . ?
C8 C9 C10 C11 0.7(5) . . . . ?
C9 C10 C11 C12 -0.6(6) . . . . ?
C10 C11 C12 C13 -0.7(5) . . . . ?
C11 C12 C13 C8 1.7(5) . . . . ?
C11 C12 C13 C14 179.0(3) . . . . ?
C9 C8 C13 C12 -1.7(5) . . . . ?
N1 C8 C13 C12 177.4(3) . . . . ?
C9 C8 C13 C14 -179.6(3) . . . . ?
N1 C8 C13 C14 -0.5(4) . . . . ?
C12 C13 C14 C15 -179.0(4) . . . . ?
C8 C13 C14 C15 -1.4(4) . . . . ?
C12 C13 C14 C16 2.3(6) . . . . ?
C8 C13 C14 C16 179.8(3) . . . . ?
C13 C14 C15 N1 2.8(4) . . . . ?
C16 C14 C15 N1 -178.5(3) . . . . ?
C8 N1 C15 C14 -3.2(4) . . . . ?
S1 N1 C15 C14 -163.3(2) . . . . ?
C15 C14 C16 C17 28.2(6) . . . . ?
C13 C14 C16 C17 -153.4(3) . . . . ?
C14 C16 C17 C18 3.4(6) . . . . ?
C14 C16 C17 C22 -170.7(3) . . . . ?
C16 C17 C18 C19 137.5(4) . . . . ?
C22 C17 C18 C19 -48.2(4) . . . . ?
C17 C18 C19 C20 54.7(4) . . . . ?
C18 C19 C20 C21 -59.5(4) . . . . ?
C19 C20 C21 C23 -179.7(3) . . . . ?
C19 C20 C21 C22 56.3(4) . . . . ?
C16 C17 C22 O3 102.8(3) . . . . ?
C18 C17 C22 O3 -71.8(3) . . . . ?
C16 C17 C22 C21 -140.3(3) . . . . ?
C18 C17 C22 C21 45.0(4) . . . . ?
C23 C21 C22 O3 -53.3(3) . . . . ?
C20 C21 C22 O3 70.1(3) . . . . ?
C23 C21 C22 C17 -171.8(3) . . . . ?
C20 C21 C22 C17 -48.5(4) . . . . ?
C24 O4 C23 O5 -5.0(5) . . . . ?
C24 O4 C23 C21 175.5(3) . . . . ?
C20 C21 C23 O5 15.4(5) . . . . ?
C22 C21 C23 O5 139.7(3) . . . . ?
C20 C21 C23 O4 -165.1(3) . . . . ?
C22 C21 C23 O4 -40.8(4) . . . . ?
C23 O4 C24 C25 -79.2(4) . . . . ?
O7 S2 C26 C27 -170.8(3) . . . . ?
O6 S2 C26 C27 -37.0(3) . . . . ?
N2 S2 C26 C27 75.5(3) . . . . ?
O7 S2 C26 C31 12.4(3) . . . . ?
O6 S2 C26 C31 146.3(3) . . . . ?
N2 S2 C26 C31 -101.2(3) . . . . ?
C31 C26 C27 C28 1.5(5) . . . . ?
S2 C26 C27 C28 -175.2(3) . . . . ?
C26 C27 C28 C29 -0.2(6) . . . . ?
C27 C28 C29 C30 -1.6(6) . . . . ?
C27 C28 C29 C32 177.3(4) . . . . ?
C28 C29 C30 C31 2.2(6) . . . . ?
C32 C29 C30 C31 -176.7(4) . . . . ?
C29 C30 C31 C26 -1.0(6) . . . . ?
C27 C26 C31 C30 -0.9(6) . . . . ?
S2 C26 C31 C30 175.8(3) . . . . ?
C40 N2 C33 C34 179.3(3) . . . . ?
S2 N2 C33 C34 20.6(5) . . . . ?
C40 N2 C33 C38 -2.7(3) . . . . ?
S2 N2 C33 C38 -161.3(2) . . . . ?
C38 C33 C34 C35 0.6(5) . . . . ?
N2 C33 C34 C35 178.4(3) . . . . ?
C33 C34 C35 C36 -1.3(5) . . . . ?
C34 C35 C36 C37 0.8(6) . . . . ?
C35 C36 C37 C38 0.4(5) . . . . ?
C36 C37 C38 C33 -1.0(5) . . . . ?
C36 C37 C38 C39 -179.4(3) . . . . ?
C34 C33 C38 C37 0.5(5) . . . . ?
N2 C33 C38 C37 -177.7(3) . . . . ?
C34 C33 C38 C39 179.2(3) . . . . ?
N2 C33 C38 C39 1.0(4) . . . . ?
C37 C38 C39 C40 179.6(4) . . . . ?
C33 C38 C39 C40 1.1(4) . . . . ?
C37 C38 C39 C41 -0.8(6) . . . . ?
C33 C38 C39 C41 -179.3(3) . . . . ?
C38 C39 C40 N2 -2.8(4) . . . . ?
C41 C39 C40 N2 177.6(3) . . . . ?
C33 N2 C40 C39 3.5(4) . . . . ?
S2 N2 C40 C39 163.0(2) . . . . ?
C40 C39 C41 C42 -41.7(6) . . . . ?
C38 C39 C41 C42 138.9(4) . . . . ?
C39 C41 C42 C43 -1.1(6) . . . . ?
C39 C41 C42 C47 179.8(3) . . . . ?
C41 C42 C43 C44 125.0(4) . . . . ?
C47 C42 C43 C44 -55.9(4) . . . . ?
C42 C43 C44 C45 56.5(4) . . . . ?
C43 C44 C45 C46 -57.6(4) . . . . ?
C44 C45 C46 C48 177.4(3) . . . . ?
C44 C45 C46 C47 56.0(4) . . . . ?
C41 C42 C47 O8 116.4(3) . . . . ?
C43 C42 C47 O8 -62.8(4) . . . . ?
C41 C42 C47 C46 -126.8(3) . . . . ?
C43 C42 C47 C46 54.0(4) . . . . ?
C48 C46 C47 O8 -54.2(4) . . . . ?
C45 C46 C47 O8 67.3(3) . . . . ?
C48 C46 C47 C42 -174.6(3) . . . . ?
C45 C46 C47 C42 -53.1(4) . . . . ?
C49 O10 C48 O9 -11.0(5) . . . . ?
C49 O10 C48 C46 169.0(3) . . . . ?
C45 C46 C48 O9 -5.1(5) . . . . ?
C47 C46 C48 O9 117.3(4) . . . . ?
C45 C46 C48 O10 174.8(3) . . . . ?
C47 C46 C48 O10 -62.7(4) . . . . ?
C48 O10 C49 C50 -86.4(4) . . . . ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_p21091217a
_database_code_depnum_ccdc_archive 'CCDC 2054732'
loop_
_audit_author_name
_audit_author_address
'Huai-Yu Bin'
;Nankai University
China
;
_audit_update_record             
;
2021-01-08 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 F O3'
_chemical_formula_weight         264.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.22580(10)
_cell_length_b                   11.19040(10)
_cell_length_c                   14.72280(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1355.23(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.817
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10637
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.964
_diffrn_reflns_theta_max         79.405
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             2751
_reflns_number_gt                2615
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.638
_reflns_Friedel_fraction_max     0.863
_reflns_Friedel_fraction_full    0.933

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²+0.1495P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0154(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 984 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2751
_refine_ls_number_parameters     195
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0912
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.6238(2) 0.38721(12) 0.39779(11) 0.0889(5) Uani 1 1 d . . . . .
O1 O 0.54501(18) 0.63947(12) 0.66212(11) 0.0634(4) Uani 1 1 d . . . . .
H1 H 0.551280 0.572932 0.685189 0.095 Uiso 1 1 calc R U . . .
O2 O 0.4521(2) 0.90303(16) 0.76246(15) 0.0932(6) Uani 1 1 d . . . . .
O3 O 0.2956(3) 0.74669(16) 0.80129(11) 0.0889(6) Uani 1 1 d D . . . .
C1 C 0.3865(2) 0.65561(16) 0.62434(13) 0.0521(4) Uani 1 1 d . . . . .
H1A H 0.310305 0.595354 0.647198 0.063 Uiso 1 1 calc R U . . .
C2 C 0.3281(2) 0.78275(17) 0.64691(14) 0.0567(5) Uani 1 1 d . . . . .
H2 H 0.209627 0.784555 0.640176 0.068 Uiso 1 1 calc R U . . .
C3 C 0.4013(3) 0.85892(17) 0.57148(15) 0.0646(5) Uani 1 1 d . . . . .
H3A H 0.515608 0.874489 0.582572 0.077 Uiso 1 1 calc R U . . .
H3B H 0.344312 0.934413 0.565650 0.077 Uiso 1 1 calc R U . . .
C4 C 0.3780(3) 0.78171(16) 0.48713(15) 0.0623(5) Uani 1 1 d . . . . .
H4A H 0.271818 0.795162 0.460387 0.075 Uiso 1 1 calc R U . . .
H4B H 0.460801 0.798985 0.442077 0.075 Uiso 1 1 calc R U . . .
C5 C 0.3934(2) 0.65479(16) 0.52124(14) 0.0521(4) Uani 1 1 d . . . . .
C6 C 0.3680(3) 0.81943(19) 0.74171(17) 0.0670(6) Uani 1 1 d . . . . .
C7 C 0.3100(9) 0.7605(6) 0.8993(3) 0.0833(17) Uani 0.734(15) 1 d D U P A 1
H7A H 0.211342 0.734065 0.929255 0.100 Uiso 0.734(15) 1 calc R U P A 1
H7B H 0.329258 0.843477 0.914945 0.100 Uiso 0.734(15) 1 calc R U P A 1
C8 C 0.4491(11) 0.6858(10) 0.9271(4) 0.112(3) Uani 0.734(15) 1 d D U P A 1
H8A H 0.430943 0.604799 0.908184 0.167 Uiso 0.734(15) 1 calc R U P A 1
H8B H 0.460278 0.688430 0.992021 0.167 Uiso 0.734(15) 1 calc R U P A 1
H8C H 0.546637 0.715515 0.899360 0.167 Uiso 0.734(15) 1 calc R U P A 1
C9 C 0.4194(3) 0.55592(17) 0.47365(14) 0.0580(5) Uani 1 1 d . . . . .
H9 H 0.425888 0.485252 0.506697 0.070 Uiso 1 1 calc R U . . .
C10 C 0.4392(3) 0.54516(16) 0.37494(14) 0.0563(5) Uani 1 1 d . . . . .
C11 C 0.5445(3) 0.46049(18) 0.33862(15) 0.0627(5) Uani 1 1 d . . . . .
C12 C 0.5757(3) 0.4476(2) 0.24791(18) 0.0728(6) Uani 1 1 d . . . . .
H12 H 0.648551 0.390084 0.227326 0.087 Uiso 1 1 calc R U . . .
C13 C 0.4965(4) 0.5218(2) 0.18772(17) 0.0752(7) Uani 1 1 d . . . . .
H13 H 0.516684 0.515515 0.125750 0.090 Uiso 1 1 calc R U . . .
C14 C 0.3876(3) 0.6051(2) 0.21944(16) 0.0728(6) Uani 1 1 d . . . . .
H14 H 0.332385 0.653970 0.178684 0.087 Uiso 1 1 calc R U . . .
C15 C 0.3599(3) 0.61662(19) 0.31114(15) 0.0632(5) Uani 1 1 d . . . . .
H15 H 0.286124 0.673745 0.331242 0.076 Uiso 1 1 calc R U . . .
C7A C 0.387(3) 0.7832(11) 0.8864(7) 0.085(4) Uani 0.266(15) 1 d D U P A 2
H7AA H 0.501136 0.797548 0.873608 0.102 Uiso 0.266(15) 1 calc R U P A 2
H7AB H 0.340251 0.854365 0.913501 0.102 Uiso 0.266(15) 1 calc R U P A 2
C8A C 0.365(4) 0.6763(18) 0.9466(10) 0.113(7) Uani 0.266(15) 1 d D U P A 2
H8AA H 0.381426 0.604717 0.911879 0.169 Uiso 0.266(15) 1 calc R U P A 2
H8AB H 0.256986 0.676485 0.971279 0.169 Uiso 0.266(15) 1 calc R U P A 2
H8AC H 0.442608 0.679226 0.995319 0.169 Uiso 0.266(15) 1 calc R U P A 2


_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
F1 C11 1.362(3) . ?
O1 C1 1.429(2) . ?
O1 H1 0.8200 . ?
O2 C6 1.203(3) . ?
O3 C6 1.337(3) . ?
O3 C7 1.456(4) . ?
O3 C7A 1.518(10) . ?
C1 C5 1.519(3) . ?
C1 C2 1.538(2) . ?
C1 H1A 0.9800 . ?
C2 C6 1.491(3) . ?
C2 C3 1.524(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.525(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.512(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C9 1.327(3) . ?
C7 C8 1.475(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.467(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.391(3) . ?
C10 C15 1.396(3) . ?
C11 C12 1.368(3) . ?
C12 C13 1.378(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C7A C8A 1.501(12) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C8A H8AA 0.9600 . ?
C8A H8AB 0.9600 . ?
C8A H8AC 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C6 O3 C7 123.3(4) . . ?
C6 O3 C7A 99.0(6) . . ?
O1 C1 C5 110.73(16) . . ?
O1 C1 C2 108.52(15) . . ?
C5 C1 C2 103.48(16) . . ?
O1 C1 H1A 111.3 . . ?
C5 C1 H1A 111.3 . . ?
C2 C1 H1A 111.3 . . ?
C6 C2 C3 116.18(18) . . ?
C6 C2 C1 112.84(17) . . ?
C3 C2 C1 103.70(16) . . ?
C6 C2 H2 107.9 . . ?
C3 C2 H2 107.9 . . ?
C1 C2 H2 107.9 . . ?
C2 C3 C4 103.12(16) . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
C4 C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
C5 C4 C3 104.55(17) . . ?
C5 C4 H4A 110.8 . . ?
C3 C4 H4A 110.8 . . ?
C5 C4 H4B 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
C9 C5 C4 128.42(18) . . ?
C9 C5 C1 122.59(18) . . ?
C4 C5 C1 108.86(16) . . ?
O2 C6 O3 124.3(2) . . ?
O2 C6 C2 125.3(2) . . ?
O3 C6 C2 110.41(19) . . ?
O3 C7 C8 106.2(4) . . ?
O3 C7 H7A 110.5 . . ?
C8 C7 H7A 110.5 . . ?
O3 C7 H7B 110.5 . . ?
C8 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 C10 127.54(18) . . ?
C5 C9 H9 116.2 . . ?
C10 C9 H9 116.2 . . ?
C11 C10 C15 115.00(19) . . ?
C11 C10 C9 120.39(19) . . ?
C15 C10 C9 124.60(19) . . ?
F1 C11 C12 118.1(2) . . ?
F1 C11 C10 117.53(19) . . ?
C12 C11 C10 124.4(2) . . ?
C11 C12 C13 118.4(2) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 122.0(2) . . ?
C14 C15 H15 119.0 . . ?
C10 C15 H15 119.0 . . ?
C8A C7A O3 102.3(9) . . ?
C8A C7A H7AA 111.3 . . ?
O3 C7A H7AA 111.3 . . ?
C8A C7A H7AB 111.3 . . ?
O3 C7A H7AB 111.3 . . ?
H7AA C7A H7AB 109.2 . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
C7A C8A H8AC 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C6 -41.6(2) . . . . ?
C5 C1 C2 C6 -159.28(18) . . . . ?
O1 C1 C2 C3 84.93(19) . . . . ?
C5 C1 C2 C3 -32.7(2) . . . . ?
C6 C2 C3 C4 165.36(18) . . . . ?
C1 C2 C3 C4 41.0(2) . . . . ?
C2 C3 C4 C5 -32.9(2) . . . . ?
C3 C4 C5 C9 -163.2(2) . . . . ?
C3 C4 C5 C1 12.7(2) . . . . ?
O1 C1 C5 C9 72.4(2) . . . . ?
C2 C1 C5 C9 -171.48(19) . . . . ?
O1 C1 C5 C4 -103.71(18) . . . . ?
C2 C1 C5 C4 12.4(2) . . . . ?
C7 O3 C6 O2 0.1(4) . . . . ?
C7A O3 C6 O2 -13.8(8) . . . . ?
C7 O3 C6 C2 -179.3(3) . . . . ?
C7A O3 C6 C2 166.8(8) . . . . ?
C3 C2 C6 O2 0.0(3) . . . . ?
C1 C2 C6 O2 119.5(2) . . . . ?
C3 C2 C6 O3 179.37(19) . . . . ?
C1 C2 C6 O3 -61.1(2) . . . . ?
C6 O3 C7 C8 -92.1(9) . . . . ?
C4 C5 C9 C10 -0.3(4) . . . . ?
C1 C5 C9 C10 -175.7(2) . . . . ?
C5 C9 C10 C11 145.5(2) . . . . ?
C5 C9 C10 C15 -33.6(3) . . . . ?
C15 C10 C11 F1 -179.20(19) . . . . ?
C9 C10 C11 F1 1.7(3) . . . . ?
C15 C10 C11 C12 2.0(3) . . . . ?
C9 C10 C11 C12 -177.1(2) . . . . ?
F1 C11 C12 C13 -179.7(2) . . . . ?
C10 C11 C12 C13 -0.9(4) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C12 C13 C14 C15 1.4(4) . . . . ?
C13 C14 C15 C10 -0.3(4) . . . . ?
C11 C10 C15 C14 -1.4(3) . . . . ?
C9 C10 C15 C14 177.7(2) . . . . ?
C6 O3 C7A C8A -158(2) . . . . ?

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.024

