# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_huangtao-555_0827_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2d0vcn
_database_code_depnum_ccdc_archive 'CCDC 2205351'
loop_
_audit_author_name
_audit_author_address
'Tao Huang'
;lanzhou university
China
;
_audit_update_record             
;
2022-09-05 deposited with the CCDC.	2023-07-21 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 H11 N O2 S'
_chemical_formula_weight         269.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   15.8096(3)
_cell_length_b                   6.82717(16)
_cell_length_c                   23.9478(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2584.81(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    297(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    1.384
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    2.200
_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      297(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            8962
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         4.633
_diffrn_reflns_theta_max         77.493
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2571
_reflns_number_gt                2204
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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    ?
_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)+(0.1277P)²+0.4174P] 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_number_reflns         2571
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1892
_refine_ls_wR_factor_gt          0.1821
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
S001 S 0.66028(3) 0.70944(13) 0.27903(3) 0.0712(3) Uani 1 1 d . . . . .
O002 O 0.18999(9) 0.6984(3) 0.41053(9) 0.0713(5) Uani 1 1 d . . . . .
O003 O 0.10938(10) 0.7032(3) 0.48384(11) 0.0872(7) Uani 1 1 d . . . . .
N004 N 0.27019(11) 0.7023(3) 0.38244(9) 0.0628(5) Uani 1 1 d . . . . .
C005 C 0.41685(11) 0.7003(3) 0.38035(8) 0.0469(5) Uani 1 1 d . . . . .
C006 C 0.33665(10) 0.6996(3) 0.47382(9) 0.0423(5) Uani 1 1 d . . . . .
C007 C 0.47886(11) 0.8418(3) 0.38882(8) 0.0498(5) Uani 1 1 d . . . . .
H007 H 0.471744 0.936943 0.416214 0.060 Uiso 1 1 calc R U . . .
C008 C 0.33717(10) 0.7020(3) 0.41324(9) 0.0458(5) Uani 1 1 d . . . . .
C009 C 0.55121(12) 0.8403(3) 0.35624(9) 0.0522(5) Uani 1 1 d . . . . .
H009 H 0.592134 0.936257 0.361668 0.063 Uiso 1 1 calc R U . . .
C00A C 0.56381(11) 0.6982(3) 0.31567(8) 0.0513(5) Uani 1 1 d . . . . .
C00B C 0.25778(12) 0.7034(3) 0.50044(9) 0.0492(5) Uani 1 1 d . . . . .
C00C C 0.42819(11) 0.5603(3) 0.33893(8) 0.0537(5) Uani 1 1 d . . . . .
H00C H 0.386117 0.467770 0.332592 0.064 Uiso 1 1 calc R U . . .
C00D C 0.40992(12) 0.6886(3) 0.50635(8) 0.0493(5) Uani 1 1 d . . . . .
H00D H 0.462753 0.685501 0.489300 0.059 Uiso 1 1 calc R U . . .
C00E C 0.18103(13) 0.7034(3) 0.46670(12) 0.0594(6) Uani 1 1 d . . . . .
C00F C 0.50144(12) 0.5564(4) 0.30678(8) 0.0573(5) Uani 1 1 d . . . . .
H00F H 0.508848 0.460447 0.279653 0.069 Uiso 1 1 calc R U . . .
C00G C 0.40371(16) 0.6822(4) 0.56375(10) 0.0633(6) Uani 1 1 d . . . . .
H00G H 0.452520 0.673179 0.585277 0.076 Uiso 1 1 calc R U . . .
C00H C 0.25276(17) 0.7001(3) 0.55838(12) 0.0676(7) Uani 1 1 d . . . . .
H00H H 0.200323 0.705307 0.575912 0.081 Uiso 1 1 calc R U . . .
C00I C 0.32534(19) 0.6892(4) 0.58966(12) 0.0736(7) Uani 1 1 d . . . . .
H00I H 0.321940 0.686406 0.628422 0.088 Uiso 1 1 calc R U . . .
C00J C 0.65430(16) 0.5116(6) 0.23031(11) 0.0867(10) Uani 1 1 d . . . . .
H00A H 0.704296 0.510417 0.207563 0.130 Uiso 1 1 calc R U . . .
H00B H 0.605438 0.528207 0.206984 0.130 Uiso 1 1 calc R U . . .
H00E H 0.649949 0.389986 0.250216 0.130 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
S001 C00A 1.7612(19) . ?
S001 C00J 1.787(3) . ?
O002 C00E 1.353(3) . ?
O002 N004 1.436(2) . ?
O003 C00E 1.205(3) . ?
N004 C008 1.291(3) . ?
C005 C00C 1.389(3) . ?
C005 C007 1.391(3) . ?
C005 C008 1.486(2) . ?
C006 C00D 1.398(3) . ?
C006 C00B 1.401(2) . ?
C006 C008 1.451(3) . ?
C007 C009 1.385(3) . ?
C007 H007 0.9300 . ?
C009 C00A 1.387(3) . ?
C009 H009 0.9300 . ?
C00A C00F 1.398(3) . ?
C00B C00H 1.390(4) . ?
C00B C00E 1.458(3) . ?
C00C C00F 1.391(3) . ?
C00C H00C 0.9300 . ?
C00D C00G 1.379(3) . ?
C00D H00D 0.9300 . ?
C00F H00F 0.9300 . ?
C00G C00I 1.387(4) . ?
C00G H00G 0.9300 . ?
C00H C00I 1.372(4) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00J H00A 0.9600 . ?
C00J H00B 0.9600 . ?
C00J H00E 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
C00A S001 C00J 104.27(11) . . ?
C00E O002 N004 123.91(16) . . ?
C008 N004 O002 117.19(19) . . ?
C00C C005 C007 119.40(18) . . ?
C00C C005 C008 119.57(17) . . ?
C007 C005 C008 120.97(17) . . ?
C00D C006 C00B 119.01(19) . . ?
C00D C006 C008 123.58(15) . . ?
C00B C006 C008 117.38(16) . . ?
C009 C007 C005 119.65(19) . . ?
C009 C007 H007 120.2 . . ?
C005 C007 H007 120.2 . . ?
N004 C008 C006 124.54(17) . . ?
N004 C008 C005 113.1(2) . . ?
C006 C008 C005 122.33(15) . . ?
C007 C009 C00A 121.24(18) . . ?
C007 C009 H009 119.4 . . ?
C00A C009 H009 119.4 . . ?
C009 C00A C00F 119.30(17) . . ?
C009 C00A S001 116.29(15) . . ?
C00F C00A S001 124.41(16) . . ?
C00H C00B C006 120.3(2) . . ?
C00H C00B C00E 120.38(19) . . ?
C006 C00B C00E 119.3(2) . . ?
C005 C00C C00F 121.07(18) . . ?
C005 C00C H00C 119.5 . . ?
C00F C00C H00C 119.5 . . ?
C00G C00D C006 119.89(19) . . ?
C00G C00D H00D 120.1 . . ?
C006 C00D H00D 120.1 . . ?
O003 C00E O002 115.9(2) . . ?
O003 C00E C00B 126.4(3) . . ?
O002 C00E C00B 117.63(17) . . ?
C00C C00F C00A 119.31(19) . . ?
C00C C00F H00F 120.3 . . ?
C00A C00F H00F 120.3 . . ?
C00D C00G C00I 120.6(2) . . ?
C00D C00G H00G 119.7 . . ?
C00I C00G H00G 119.7 . . ?
C00I C00H C00B 119.9(2) . . ?
C00I C00H H00H 120.1 . . ?
C00B C00H H00H 120.1 . . ?
C00H C00I C00G 120.3(2) . . ?
C00H C00I H00I 119.8 . . ?
C00G C00I H00I 119.8 . . ?
S001 C00J H00A 109.5 . . ?
S001 C00J H00B 109.5 . . ?
H00A C00J H00B 109.5 . . ?
S001 C00J H00E 109.5 . . ?
H00A C00J H00E 109.5 . . ?
H00B C00J H00E 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
C00E O002 N004 C008 3.1(3) . . . . ?
C00C C005 C007 C009 -0.6(3) . . . . ?
C008 C005 C007 C009 -177.86(18) . . . . ?
O002 N004 C008 C006 -0.5(3) . . . . ?
O002 N004 C008 C005 178.32(16) . . . . ?
C00D C006 C008 N004 176.37(19) . . . . ?
C00B C006 C008 N004 -1.8(3) . . . . ?
C00D C006 C008 C005 -2.4(3) . . . . ?
C00B C006 C008 C005 179.43(16) . . . . ?
C00C C005 C008 N004 -51.8(3) . . . . ?
C007 C005 C008 N004 125.5(2) . . . . ?
C00C C005 C008 C006 127.1(2) . . . . ?
C007 C005 C008 C006 -55.6(3) . . . . ?
C005 C007 C009 C00A -0.9(3) . . . . ?
C007 C009 C00A C00F 1.3(3) . . . . ?
C007 C009 C00A S001 -177.94(16) . . . . ?
C00J S001 C00A C009 -179.0(2) . . . . ?
C00J S001 C00A C00F 1.8(2) . . . . ?
C00D C006 C00B C00H 1.3(3) . . . . ?
C008 C006 C00B C00H 179.57(18) . . . . ?
C00D C006 C00B C00E -176.44(17) . . . . ?
C008 C006 C00B C00E 1.9(3) . . . . ?
C007 C005 C00C C00F 1.7(3) . . . . ?
C008 C005 C00C C00F 179.01(19) . . . . ?
C00B C006 C00D C00G -0.2(3) . . . . ?
C008 C006 C00D C00G -178.40(19) . . . . ?
N004 O002 C00E O003 178.51(19) . . . . ?
N004 O002 C00E C00B -3.0(3) . . . . ?
C00H C00B C00E O003 1.0(3) . . . . ?
C006 C00B C00E O003 178.74(19) . . . . ?
C00H C00B C00E O002 -177.31(18) . . . . ?
C006 C00B C00E O002 0.4(3) . . . . ?
C005 C00C C00F C00A -1.3(3) . . . . ?
C009 C00A C00F C00C -0.2(3) . . . . ?
S001 C00A C00F C00C 178.98(17) . . . . ?
C006 C00D C00G C00I -0.8(3) . . . . ?
C006 C00B C00H C00I -1.3(3) . . . . ?
C00E C00B C00H C00I 176.4(2) . . . . ?
C00B C00H C00I C00G 0.3(4) . . . . ?
C00D C00G C00I C00H 0.8(4) . . . . ?

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_huangtao-529_0827-2_auto
_database_code_depnum_ccdc_archive 'CCDC 2204175'
loop_
_audit_author_name
_audit_author_address
'Tao Huang'
;lanzhou university
China
;
_audit_update_record             
;
2022-09-05 deposited with the CCDC.	2023-07-21 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 H10 F N O2'
_chemical_formula_weight         255.24

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6882(10)
_cell_length_b                   8.4126(11)
_cell_length_c                   10.4035(8)
_cell_angle_alpha                91.427(8)
_cell_angle_beta                 99.305(9)
_cell_angle_gamma                114.923(13)
_cell_volume                     598.92(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(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    1.415
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.880
_shelx_estimated_absorpt_T_min   0.851
_shelx_estimated_absorpt_T_max   0.902
_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      293(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            5844
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_av_R_equivalents  0.0856
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.330
_diffrn_reflns_theta_max         77.877
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             2290
_reflns_number_gt                1594
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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    ?
_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)+(0.1854P)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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.004(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2290
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.0886
_refine_ls_wR_factor_ref         0.2674
_refine_ls_wR_factor_gt          0.2382
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.8631(3) 0.2931(3) 0.0121(2) 0.0869(8) Uani 1 1 d . . . . .
O1 O 0.2387(4) 0.0679(3) 0.5601(2) 0.0686(7) Uani 1 1 d . . . . .
O2 O 0.2738(4) 0.2451(4) 0.7288(2) 0.0836(9) Uani 1 1 d . . . . .
N2 N 0.2043(4) 0.0187(3) 0.4235(3) 0.0628(7) Uani 1 1 d . . . . .
C2 C 0.2442(4) 0.3523(4) 0.5212(3) 0.0501(7) Uani 1 1 d . . . . .
C1 C 0.2141(4) 0.3056(3) 0.3878(3) 0.0458(7) Uani 1 1 d . . . . .
C15 C 0.1934(4) 0.1314(3) 0.3451(3) 0.0509(7) Uani 1 1 d . . . . .
C3 C 0.1630(4) 0.0678(4) 0.2026(3) 0.0583(8) Uani 1 1 d . . . . .
H3A H 0.101868 -0.060045 0.191799 0.070 Uiso 1 1 calc R U . . .
H3B H 0.075031 0.107567 0.150821 0.070 Uiso 1 1 calc R U . . .
C4 C 0.3514(4) 0.1337(3) 0.1524(2) 0.0508(7) Uani 1 1 d . . . . .
C5 C 0.2221(5) 0.5887(4) 0.3498(3) 0.0663(9) Uani 1 1 d . . . . .
H5 H 0.213612 0.668830 0.291914 0.080 Uiso 1 1 calc R U . . .
C6 C 0.2019(5) 0.4266(4) 0.3011(3) 0.0562(8) Uani 1 1 d . . . . .
H6 H 0.180241 0.397857 0.211245 0.067 Uiso 1 1 calc R U . . .
C7 C 0.2545(5) 0.2260(4) 0.6136(3) 0.0575(8) Uani 1 1 d . . . . .
C8 C 0.3849(5) 0.2395(4) 0.0506(3) 0.0628(9) Uani 1 1 d . . . . .
H8 H 0.289329 0.273557 0.013003 0.075 Uiso 1 1 calc R U . . .
C9 C 0.6951(5) 0.2434(4) 0.0600(3) 0.0592(8) Uani 1 1 d . . . . .
C10 C 0.4974(5) 0.0846(4) 0.2056(3) 0.0539(7) Uani 1 1 d . . . . .
H10 H 0.477912 0.013546 0.273943 0.065 Uiso 1 1 calc R U . . .
C11 C 0.2546(5) 0.6341(4) 0.4824(4) 0.0670(9) Uani 1 1 d . . . . .
H11 H 0.268654 0.744332 0.513494 0.080 Uiso 1 1 calc R U . . .
C12 C 0.2663(5) 0.5166(4) 0.5691(3) 0.0601(8) Uani 1 1 d . . . . .
H12 H 0.288738 0.546858 0.658793 0.072 Uiso 1 1 calc R U . . .
C13 C 0.6694(5) 0.1381(4) 0.1602(3) 0.0591(8) Uani 1 1 d . . . . .
H13 H 0.765447 0.103843 0.196337 0.071 Uiso 1 1 calc R U . . .
C14 C 0.5573(6) 0.2952(4) 0.0039(3) 0.0667(9) Uani 1 1 d . . . . .
H14 H 0.578753 0.366507 -0.064249 0.080 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
F1 C9 1.361(4) . ?
O1 C7 1.377(4) . ?
O1 N2 1.421(4) . ?
O2 C7 1.183(4) . ?
N2 C15 1.285(4) . ?
C2 C1 1.388(4) . ?
C2 C12 1.389(4) . ?
C2 C7 1.468(4) . ?
C1 C6 1.399(4) . ?
C1 C15 1.456(4) . ?
C15 C3 1.511(4) . ?
C3 C4 1.504(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C8 1.386(4) . ?
C4 C10 1.393(4) . ?
C5 C11 1.377(5) . ?
C5 C6 1.379(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C14 1.382(5) . ?
C8 H8 0.9300 . ?
C9 C14 1.362(5) . ?
C9 C13 1.370(5) . ?
C10 C13 1.373(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

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
C7 O1 N2 124.2(2) . . ?
C15 N2 O1 117.8(2) . . ?
C1 C2 C12 121.3(2) . . ?
C1 C2 C7 119.4(3) . . ?
C12 C2 C7 119.4(3) . . ?
C2 C1 C6 118.6(2) . . ?
C2 C1 C15 118.1(2) . . ?
C6 C1 C15 123.3(3) . . ?
N2 C15 C1 124.0(3) . . ?
N2 C15 C3 113.4(3) . . ?
C1 C15 C3 122.6(2) . . ?
C4 C3 C15 112.3(2) . . ?
C4 C3 H3A 109.2 . . ?
C15 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C15 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C8 C4 C10 117.7(3) . . ?
C8 C4 C3 122.2(3) . . ?
C10 C4 C3 120.1(3) . . ?
C11 C5 C6 121.2(3) . . ?
C11 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
O2 C7 O1 116.6(3) . . ?
O2 C7 C2 126.9(3) . . ?
O1 C7 C2 116.5(3) . . ?
C14 C8 C4 121.3(3) . . ?
C14 C8 H8 119.3 . . ?
C4 C8 H8 119.3 . . ?
F1 C9 C14 119.0(3) . . ?
F1 C9 C13 118.3(3) . . ?
C14 C9 C13 122.7(3) . . ?
C13 C10 C4 121.9(3) . . ?
C13 C10 H10 119.1 . . ?
C4 C10 H10 119.1 . . ?
C12 C11 C5 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C5 C11 H11 120.0 . . ?
C11 C12 C2 119.3(3) . . ?
C11 C12 H12 120.3 . . ?
C2 C12 H12 120.3 . . ?
C9 C13 C10 118.0(3) . . ?
C9 C13 H13 121.0 . . ?
C10 C13 H13 121.0 . . ?
C9 C14 C8 118.5(3) . . ?
C9 C14 H14 120.8 . . ?
C8 C14 H14 120.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 O1 N2 C15 2.3(5) . . . . ?
C12 C2 C1 C6 -1.4(4) . . . . ?
C7 C2 C1 C6 179.1(3) . . . . ?
C12 C2 C1 C15 179.6(3) . . . . ?
C7 C2 C1 C15 0.1(4) . . . . ?
O1 N2 C15 C1 0.0(5) . . . . ?
O1 N2 C15 C3 178.2(2) . . . . ?
C2 C1 C15 N2 -1.1(4) . . . . ?
C6 C1 C15 N2 180.0(3) . . . . ?
C2 C1 C15 C3 -179.1(2) . . . . ?
C6 C1 C15 C3 2.0(4) . . . . ?
N2 C15 C3 C4 -96.6(3) . . . . ?
C1 C15 C3 C4 81.6(3) . . . . ?
C15 C3 C4 C8 -119.1(3) . . . . ?
C15 C3 C4 C10 62.9(3) . . . . ?
C11 C5 C6 C1 0.1(5) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
C15 C1 C6 C5 179.6(3) . . . . ?
N2 O1 C7 O2 176.4(3) . . . . ?
N2 O1 C7 C2 -3.1(4) . . . . ?
C1 C2 C7 O2 -177.7(3) . . . . ?
C12 C2 C7 O2 2.8(5) . . . . ?
C1 C2 C7 O1 1.8(4) . . . . ?
C12 C2 C7 O1 -177.7(3) . . . . ?
C10 C4 C8 C14 -0.4(4) . . . . ?
C3 C4 C8 C14 -178.4(2) . . . . ?
C8 C4 C10 C13 0.1(4) . . . . ?
C3 C4 C10 C13 178.2(2) . . . . ?
C6 C5 C11 C12 -0.4(5) . . . . ?
C5 C11 C12 C2 -0.3(5) . . . . ?
C1 C2 C12 C11 1.2(5) . . . . ?
C7 C2 C12 C11 -179.3(3) . . . . ?
F1 C9 C13 C10 -178.3(2) . . . . ?
C14 C9 C13 C10 -0.5(4) . . . . ?
C4 C10 C13 C9 0.3(4) . . . . ?
F1 C9 C14 C8 178.0(2) . . . . ?
C13 C9 C14 C8 0.2(5) . . . . ?
C4 C8 C14 C9 0.2(4) . . . . ?

_refine_diff_density_max         0.441
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.089

