# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_18105
_database_code_depnum_ccdc_archive 'CCDC 2083051'
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2021-07-06 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         'C18 H19 F N2 O2 S'
_chemical_formula_sum            'C18 H19 F N2 O2 S'
_chemical_formula_weight         346.41

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'
F F 0.0171 0.0103 '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      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                   18.644(4)
_cell_length_b                   9.1535(18)
_cell_length_c                   20.027(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3417.7(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    822
_cell_measurement_theta_min      2.680
_cell_measurement_theta_max      21.520

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             1456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.212
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.726
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_process_details   
;
absoprtion correction based on 5721 reflections(SADABS);Rint 0.0776 before
correction and 0.0502 after.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24963
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_av_R_equivalents  0.1007
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.034
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3361
_reflns_number_gt                2263
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0473P)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_number_reflns         3361
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0511
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.1005
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_restrained_S_all      0.958
_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 1.09142(3) 0.40441(7) 0.38337(3) 0.02834(18) Uani 1 1 d . . . . .
F1 F 0.98791(7) 0.31243(15) 0.20003(7) 0.0383(4) Uani 1 1 d . . . . .
O1 O 1.05600(9) 0.32999(18) 0.43629(8) 0.0330(4) Uani 1 1 d . . . . .
O2 O 1.15326(8) 0.34152(19) 0.35255(8) 0.0359(5) Uani 1 1 d . . . . .
N1 N 0.96772(10) 0.4796(2) 0.34477(10) 0.0274(5) Uani 1 1 d . . . . .
N2 N 1.03270(10) 0.4207(2) 0.32114(9) 0.0272(5) Uani 1 1 d . . . . .
C1 C 1.06099(13) 0.4788(3) 0.25771(12) 0.0297(6) Uani 1 1 d . . . . .
H1A H 1.104344 0.423761 0.244273 0.036 Uiso 1 1 calc R U . . .
H1B H 1.074274 0.582896 0.263106 0.036 Uiso 1 1 calc R U . . .
C2 C 1.00356(13) 0.4637(3) 0.20505(12) 0.0292(6) Uani 1 1 d . . . . .
C3 C 0.93543(12) 0.5379(3) 0.22772(12) 0.0292(6) Uani 1 1 d . . . . .
H3A H 0.936724 0.641272 0.213223 0.035 Uiso 1 1 calc R U . . .
H3B H 0.894149 0.490720 0.205315 0.035 Uiso 1 1 calc R U . . .
C4 C 0.92358(12) 0.5331(3) 0.30193(12) 0.0268(6) Uani 1 1 d . . . . .
C5 C 0.85713(12) 0.5985(3) 0.33026(12) 0.0282(6) Uani 1 1 d . . . . .
C6 C 0.80303(14) 0.6520(3) 0.28871(14) 0.0421(7) Uani 1 1 d . . . . .
H6 H 0.808041 0.644015 0.241646 0.051 Uiso 1 1 calc R U . . .
C7 C 0.74228(15) 0.7163(3) 0.31516(16) 0.0516(8) Uani 1 1 d . . . . .
H7 H 0.705787 0.751363 0.286193 0.062 Uiso 1 1 calc R U . . .
C8 C 0.73429(15) 0.7298(3) 0.38349(17) 0.0503(8) Uani 1 1 d . . . . .
H8 H 0.692708 0.774737 0.401672 0.060 Uiso 1 1 calc R U . . .
C9 C 0.78737(15) 0.6775(3) 0.42485(14) 0.0433(7) Uani 1 1 d . . . . .
H9 H 0.781993 0.685794 0.471873 0.052 Uiso 1 1 calc R U . . .
C10 C 0.84836(14) 0.6130(3) 0.39896(13) 0.0359(7) Uani 1 1 d . . . . .
H10 H 0.884593 0.578227 0.428297 0.043 Uiso 1 1 calc R U . . .
C11 C 1.03011(14) 0.5143(3) 0.13760(12) 0.0405(7) Uani 1 1 d . . . . .
H11A H 1.043744 0.617562 0.140197 0.061 Uiso 1 1 calc R U . . .
H11B H 0.991919 0.502232 0.104432 0.061 Uiso 1 1 calc R U . . .
H11C H 1.071863 0.456012 0.124444 0.061 Uiso 1 1 calc R U . . .
C12 C 1.11212(12) 0.5826(3) 0.40925(12) 0.0271(6) Uani 1 1 d . . . . .
C13 C 1.16801(13) 0.6582(3) 0.37921(13) 0.0338(6) Uani 1 1 d . . . . .
H13 H 1.196094 0.613153 0.345417 0.041 Uiso 1 1 calc R U . . .
C14 C 1.18221(13) 0.7990(3) 0.39894(13) 0.0373(7) Uani 1 1 d . . . . .
H14 H 1.220631 0.850667 0.378631 0.045 Uiso 1 1 calc R U . . .
C15 C 1.14146(13) 0.8675(3) 0.44810(13) 0.0326(6) Uani 1 1 d . . . . .
C16 C 1.08606(14) 0.7896(3) 0.47706(12) 0.0358(6) Uani 1 1 d . . . . .
H16 H 1.058003 0.834483 0.510939 0.043 Uiso 1 1 calc R U . . .
C17 C 1.07060(14) 0.6488(3) 0.45799(12) 0.0330(6) Uani 1 1 d . . . . .
H17 H 1.031878 0.597534 0.478005 0.040 Uiso 1 1 calc R U . . .
C18 C 1.15794(15) 1.0211(3) 0.47028(15) 0.0464(8) Uani 1 1 d . . . . .
H18A H 1.113121 1.071877 0.480982 0.070 Uiso 1 1 calc R U . . .
H18B H 1.182786 1.073120 0.434301 0.070 Uiso 1 1 calc R U . . .
H18C H 1.188649 1.018221 0.509971 0.070 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 1.4226(17) . ?
S1 O2 1.4288(17) . ?
S1 N2 1.6655(19) . ?
S1 C12 1.755(3) . ?
F1 C2 1.418(3) . ?
N1 C4 1.286(3) . ?
N1 N2 1.408(3) . ?
N2 C1 1.475(3) . ?
C1 C2 1.509(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.510(3) . ?
C2 C11 1.511(3) . ?
C3 C4 1.503(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.488(3) . ?
C5 C10 1.392(3) . ?
C5 C6 1.396(3) . ?
C6 C7 1.382(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.382(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.377(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.386(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.373(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(3) . ?
C15 C18 1.506(4) . ?
C16 C17 1.375(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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 120.23(11) . . ?
O1 S1 N2 107.18(10) . . ?
O2 S1 N2 104.08(10) . . ?
O1 S1 C12 109.10(11) . . ?
O2 S1 C12 108.95(11) . . ?
N2 S1 C12 106.39(11) . . ?
C4 N1 N2 118.2(2) . . ?
N1 N2 C1 117.33(18) . . ?
N1 N2 S1 110.40(14) . . ?
C1 N2 S1 116.22(15) . . ?
N2 C1 C2 108.37(19) . . ?
N2 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
N2 C1 H1B 110.0 . . ?
C2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
F1 C2 C1 106.58(19) . . ?
F1 C2 C3 106.70(19) . . ?
C1 C2 C3 110.2(2) . . ?
F1 C2 C11 107.66(19) . . ?
C1 C2 C11 111.3(2) . . ?
C3 C2 C11 114.0(2) . . ?
C4 C3 C2 114.1(2) . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
N1 C4 C5 115.6(2) . . ?
N1 C4 C3 125.2(2) . . ?
C5 C4 C3 119.2(2) . . ?
C10 C5 C6 118.1(2) . . ?
C10 C5 C4 120.9(2) . . ?
C6 C5 C4 121.0(2) . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.4(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 119.1(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C5 120.5(2) . . ?
C9 C10 H10 119.7 . . ?
C5 C10 H10 119.7 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 120.4(2) . . ?
C17 C12 S1 119.47(19) . . ?
C13 C12 S1 120.0(2) . . ?
C14 C13 C12 119.2(2) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 121.4(2) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 118.2(2) . . ?
C16 C15 C18 120.7(2) . . ?
C14 C15 C18 121.2(2) . . ?
C17 C16 C15 121.6(2) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C16 C17 C12 119.3(2) . . ?
C16 C17 H17 120.4 . . ?
C12 C17 H17 120.4 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C4 N1 N2 C1 26.6(3) . . . . ?
C4 N1 N2 S1 162.87(17) . . . . ?
O1 S1 N2 N1 50.50(17) . . . . ?
O2 S1 N2 N1 178.89(14) . . . . ?
C12 S1 N2 N1 -66.10(17) . . . . ?
O1 S1 N2 C1 -172.67(16) . . . . ?
O2 S1 N2 C1 -44.29(19) . . . . ?
C12 S1 N2 C1 70.72(19) . . . . ?
N1 N2 C1 C2 -54.9(3) . . . . ?
S1 N2 C1 C2 171.33(15) . . . . ?
N2 C1 C2 F1 -60.0(2) . . . . ?
N2 C1 C2 C3 55.4(3) . . . . ?
N2 C1 C2 C11 -177.17(19) . . . . ?
F1 C2 C3 C4 83.1(2) . . . . ?
C1 C2 C3 C4 -32.3(3) . . . . ?
C11 C2 C3 C4 -158.3(2) . . . . ?
N2 N1 C4 C5 -177.86(19) . . . . ?
N2 N1 C4 C3 0.2(3) . . . . ?
C2 C3 C4 N1 3.9(3) . . . . ?
C2 C3 C4 C5 -178.1(2) . . . . ?
N1 C4 C5 C10 6.4(3) . . . . ?
C3 C4 C5 C10 -171.8(2) . . . . ?
N1 C4 C5 C6 -176.0(2) . . . . ?
C3 C4 C5 C6 5.8(3) . . . . ?
C10 C5 C6 C7 -0.5(4) . . . . ?
C4 C5 C6 C7 -178.2(2) . . . . ?
C5 C6 C7 C8 0.5(4) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
C7 C8 C9 C10 0.5(4) . . . . ?
C8 C9 C10 C5 -0.5(4) . . . . ?
C6 C5 C10 C9 0.5(4) . . . . ?
C4 C5 C10 C9 178.2(2) . . . . ?
O1 S1 C12 C17 -26.6(2) . . . . ?
O2 S1 C12 C17 -159.59(19) . . . . ?
N2 S1 C12 C17 88.7(2) . . . . ?
O1 S1 C12 C13 155.85(19) . . . . ?
O2 S1 C12 C13 22.8(2) . . . . ?
N2 S1 C12 C13 -88.8(2) . . . . ?
C17 C12 C13 C14 0.8(4) . . . . ?
S1 C12 C13 C14 178.32(19) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
C13 C14 C15 C16 0.3(4) . . . . ?
C13 C14 C15 C18 179.1(2) . . . . ?
C14 C15 C16 C17 -0.5(4) . . . . ?
C18 C15 C16 C17 -179.4(2) . . . . ?
C15 C16 C17 C12 0.9(4) . . . . ?
C13 C12 C17 C16 -1.0(4) . . . . ?
S1 C12 C17 C16 -178.59(19) . . . . ?

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_20020
_database_code_depnum_ccdc_archive 'CCDC 2083056'
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2021-07-06 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         'C15 H21 F N2 O2 S'
_chemical_formula_sum            'C15 H21 F N2 O2 S'
_chemical_formula_weight         312.40

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'
F F 0.0171 0.0103 '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      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                   8.315(3)
_cell_length_b                   11.835(5)
_cell_length_c                   16.239(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1598.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    912
_cell_measurement_theta_min      2.994
_cell_measurement_theta_max      26.343

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.219
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.572
_exptl_absorpt_correction_T_max  0.875
_exptl_absorpt_process_details   
;
absoprtion correction based on 6307 reflections(SADABS);Rint 0.0849 before
correction and 0.0510 after.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12402
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.129
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3140
_reflns_number_gt                2670
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component inversion 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)+(0.0544P)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 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3140
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1101
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
F1 F 0.8868(3) 1.0400(2) 0.66409(13) 0.0743(7) Uani 1 1 d . . . . .
S1 S 0.41184(11) 1.03341(8) 0.75868(6) 0.0474(3) Uani 1 1 d . . . . .
O1 O 0.3562(3) 1.1456(2) 0.77128(19) 0.0653(8) Uani 1 1 d . . . . .
O2 O 0.3681(3) 0.9732(3) 0.68557(16) 0.0614(7) Uani 1 1 d . . . . .
N1 N 0.6659(4) 1.0927(2) 0.82943(18) 0.0421(7) Uani 1 1 d . . . . .
N2 N 0.6120(3) 1.0383(2) 0.75803(16) 0.0427(6) Uani 1 1 d . . . . .
C1 C 0.6947(4) 0.9335(3) 0.7354(2) 0.0431(8) Uani 1 1 d . . . . .
H1A H 0.651006 0.904265 0.682845 0.052 Uiso 1 1 calc R U . . .
H1B H 0.677356 0.875636 0.778495 0.052 Uiso 1 1 calc R U . . .
C2 C 0.8708(4) 0.9569(3) 0.7264(2) 0.0463(8) Uani 1 1 d . . . . .
C3 C 0.9345(4) 1.0085(3) 0.8056(2) 0.0494(9) Uani 1 1 d . . . . .
H3A H 0.972501 0.947086 0.842103 0.059 Uiso 1 1 calc R U . . .
H3B H 1.028010 1.056982 0.792379 0.059 Uiso 1 1 calc R U . . .
C4 C 0.8116(4) 1.0779(3) 0.8511(2) 0.0406(8) Uani 1 1 d . . . . .
C5 C 0.8671(5) 1.1325(3) 0.9300(2) 0.0570(11) Uani 1 1 d . . . . .
H5 H 0.972353 1.170252 0.918691 0.068 Uiso 1 1 calc R U . . .
C6 C 0.7505(7) 1.2229(4) 0.9607(3) 0.0831(16) Uani 1 1 d . . . . .
H6A H 0.648034 1.187483 0.975739 0.125 Uiso 1 1 calc R U . . .
H6B H 0.732202 1.278562 0.917015 0.125 Uiso 1 1 calc R U . . .
H6C H 0.796290 1.260629 1.009018 0.125 Uiso 1 1 calc R U . . .
C7 C 0.8958(6) 1.0431(5) 0.9963(2) 0.0765(13) Uani 1 1 d . . . . .
H7A H 0.963889 0.982897 0.973952 0.115 Uiso 1 1 calc R U . . .
H7B H 0.792505 1.011266 1.013748 0.115 Uiso 1 1 calc R U . . .
H7C H 0.949432 1.077930 1.043666 0.115 Uiso 1 1 calc R U . . .
C8 C 0.9618(5) 0.8540(4) 0.7004(3) 0.0694(13) Uani 1 1 d . . . . .
H8A H 1.075740 0.873089 0.693696 0.104 Uiso 1 1 calc R U . . .
H8B H 0.918789 0.826346 0.647945 0.104 Uiso 1 1 calc R U . . .
H8C H 0.950502 0.795208 0.742462 0.104 Uiso 1 1 calc R U . . .
C9 C 0.3611(4) 0.9517(3) 0.8450(2) 0.0408(8) Uani 1 1 d . . . . .
C10 C 0.3354(4) 0.8373(3) 0.8377(2) 0.0476(9) Uani 1 1 d . . . . .
H10 H 0.342420 0.801293 0.785551 0.057 Uiso 1 1 calc R U . . .
C11 C 0.2994(5) 0.7759(3) 0.9072(3) 0.0559(11) Uani 1 1 d . . . . .
H11 H 0.280264 0.697071 0.902078 0.067 Uiso 1 1 calc R U . . .
C12 C 0.2900(5) 0.8254(3) 0.9848(3) 0.0542(10) Uani 1 1 d . . . . .
C13 C 0.3185(5) 0.9404(3) 0.9896(2) 0.0582(11) Uani 1 1 d . . . . .
H13 H 0.313888 0.976770 1.041706 0.070 Uiso 1 1 calc R U . . .
C14 C 0.3531(5) 1.0030(3) 0.9210(2) 0.0540(10) Uani 1 1 d . . . . .
H14 H 0.371692 1.081926 0.925824 0.065 Uiso 1 1 calc R U . . .
C15 C 0.2549(7) 0.7579(4) 1.0606(3) 0.0854(16) Uani 1 1 d . . . . .
H15A H 0.356255 0.734607 1.086385 0.128 Uiso 1 1 calc R U . . .
H15B H 0.192465 0.690680 1.045718 0.128 Uiso 1 1 calc R U . . .
H15C H 0.193074 0.804030 1.099453 0.128 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 C2 1.417(4) . ?
S1 O1 1.421(3) . ?
S1 O2 1.431(3) . ?
S1 N2 1.666(3) . ?
S1 C9 1.755(4) . ?
N1 C4 1.273(5) . ?
N1 N2 1.400(4) . ?
N2 C1 1.465(4) . ?
C1 C2 1.497(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C8 1.495(5) . ?
C2 C3 1.519(5) . ?
C3 C4 1.504(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.508(5) . ?
C5 C7 1.527(6) . ?
C5 C6 1.528(6) . ?
C5 H5 1.0000 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.376(5) . ?
C9 C14 1.377(5) . ?
C10 C11 1.375(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(6) . ?
C12 C15 1.497(6) . ?
C13 C14 1.368(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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 120.10(18) . . ?
O1 S1 N2 107.09(17) . . ?
O2 S1 N2 105.43(16) . . ?
O1 S1 C9 108.76(17) . . ?
O2 S1 C9 109.10(16) . . ?
N2 S1 C9 105.35(15) . . ?
C4 N1 N2 118.0(3) . . ?
N1 N2 C1 116.5(3) . . ?
N1 N2 S1 109.3(2) . . ?
C1 N2 S1 116.2(2) . . ?
N2 C1 C2 109.1(3) . . ?
N2 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
N2 C1 H1B 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
F1 C2 C8 108.4(3) . . ?
F1 C2 C1 106.8(3) . . ?
C8 C2 C1 111.8(3) . . ?
F1 C2 C3 107.0(3) . . ?
C8 C2 C3 113.0(3) . . ?
C1 C2 C3 109.4(3) . . ?
C4 C3 C2 113.5(3) . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
N1 C4 C3 125.8(3) . . ?
N1 C4 C5 117.8(3) . . ?
C3 C4 C5 116.3(3) . . ?
C4 C5 C7 110.5(3) . . ?
C4 C5 C6 112.5(4) . . ?
C7 C5 C6 110.8(4) . . ?
C4 C5 H5 107.6 . . ?
C7 C5 H5 107.6 . . ?
C6 C5 H5 107.6 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C8 H8A 109.5 . . ?
C2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 120.3(3) . . ?
C10 C9 S1 120.7(3) . . ?
C14 C9 S1 119.0(3) . . ?
C11 C10 C9 118.9(3) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 122.2(4) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C13 C12 C11 117.1(4) . . ?
C13 C12 C15 120.9(4) . . ?
C11 C12 C15 122.1(4) . . ?
C14 C13 C12 121.5(4) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C13 C14 C9 120.1(3) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C4 N1 N2 C1 27.0(4) . . . . ?
C4 N1 N2 S1 161.2(3) . . . . ?
O1 S1 N2 N1 53.1(2) . . . . ?
O2 S1 N2 N1 -177.9(2) . . . . ?
C9 S1 N2 N1 -62.6(2) . . . . ?
O1 S1 N2 C1 -172.5(2) . . . . ?
O2 S1 N2 C1 -43.5(3) . . . . ?
C9 S1 N2 C1 71.8(3) . . . . ?
N1 N2 C1 C2 -56.8(4) . . . . ?
S1 N2 C1 C2 172.1(2) . . . . ?
N2 C1 C2 F1 -59.5(4) . . . . ?
N2 C1 C2 C8 -178.0(3) . . . . ?
N2 C1 C2 C3 56.1(4) . . . . ?
F1 C2 C3 C4 84.7(3) . . . . ?
C8 C2 C3 C4 -156.0(3) . . . . ?
C1 C2 C3 C4 -30.7(4) . . . . ?
N2 N1 C4 C3 1.4(5) . . . . ?
N2 N1 C4 C5 -177.4(3) . . . . ?
C2 C3 C4 N1 1.7(5) . . . . ?
C2 C3 C4 C5 -179.5(3) . . . . ?
N1 C4 C5 C7 109.4(4) . . . . ?
C3 C4 C5 C7 -69.5(4) . . . . ?
N1 C4 C5 C6 -15.0(5) . . . . ?
C3 C4 C5 C6 166.1(3) . . . . ?
O1 S1 C9 C10 151.8(3) . . . . ?
O2 S1 C9 C10 19.1(3) . . . . ?
N2 S1 C9 C10 -93.7(3) . . . . ?
O1 S1 C9 C14 -30.6(3) . . . . ?
O2 S1 C9 C14 -163.3(3) . . . . ?
N2 S1 C9 C14 83.9(3) . . . . ?
C14 C9 C10 C11 1.0(5) . . . . ?
S1 C9 C10 C11 178.6(3) . . . . ?
C9 C10 C11 C12 -0.8(6) . . . . ?
C10 C11 C12 C13 0.1(6) . . . . ?
C10 C11 C12 C15 -178.4(4) . . . . ?
C11 C12 C13 C14 0.5(7) . . . . ?
C15 C12 C13 C14 179.0(5) . . . . ?
C12 C13 C14 C9 -0.3(7) . . . . ?
C10 C9 C14 C13 -0.5(6) . . . . ?
S1 C9 C14 C13 -178.1(3) . . . . ?

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_19002
_database_code_depnum_ccdc_archive 'CCDC 2083055'
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2021-07-06 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            'C16 H17 F N2 O2 S2'
_chemical_formula_weight         352.43

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'
F F 0.0171 0.0103 '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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   20.185(3)
_cell_length_b                   20.185(3)
_cell_length_c                   21.625(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7630(3)
_cell_formula_units_Z            18
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    684
_cell_measurement_theta_min      2.513
_cell_measurement_theta_max      26.133

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             3312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.334
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.580
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_process_details   
;
absoprtion correction based on 4930 reflections(SADABS);Rinto 0.0736 before
correction and 0.0530 after.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19944
_diffrn_reflns_av_unetI/netI     0.0731
_diffrn_reflns_av_R_equivalents  0.0973
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.018
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3323
_reflns_number_gt                2143
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0511P)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_number_reflns         3323
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1225
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_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 -0.04599(10) 0.18155(10) 0.02802(9) 0.0582(5) Uani 1 1 d . . . . .
S1 S -0.07510(4) 0.33396(4) 0.14520(4) 0.0429(2) Uani 1 1 d . . . . .
S3 S 0.10323(5) 0.49329(5) -0.02132(4) 0.0467(2) Uani 1 1 d . . . . .
O1 O -0.11835(11) 0.27349(11) 0.18790(10) 0.0509(6) Uani 1 1 d . . . . .
O2 O -0.11224(11) 0.36417(12) 0.10796(10) 0.0525(6) Uani 1 1 d . . . . .
N1 N 0.01357(14) 0.35854(14) 0.05688(11) 0.0413(6) Uani 1 1 d . . . . .
N2 N -0.03534(14) 0.29995(14) 0.09680(11) 0.0396(6) Uani 1 1 d . . . . .
C1 C -0.01008(18) 0.24871(17) 0.12155(14) 0.0432(8) Uani 1 1 d . . . . .
H1A H -0.052940 0.205266 0.143307 0.052 Uiso 1 1 calc R U . . .
H1B H 0.032032 0.276591 0.151487 0.052 Uiso 1 1 calc R U . . .
C2 C 0.01703(18) 0.21952(17) 0.06879(15) 0.0448(8) Uani 1 1 d . . . . .
C3 C 0.07940(17) 0.28536(16) 0.03324(15) 0.0431(8) Uani 1 1 d . . . . .
H3A H 0.128970 0.302404 0.054171 0.052 Uiso 1 1 calc R U . . .
H3B H 0.082690 0.267666 -0.008745 0.052 Uiso 1 1 calc R U . . .
C4 C 0.06602(16) 0.35196(16) 0.02790(14) 0.0385(7) Uani 1 1 d . . . . .
C5 C 0.11528(16) 0.41469(16) -0.01264(14) 0.0390(7) Uani 1 1 d . . . . .
C6 C 0.17465(17) 0.42191(18) -0.04823(14) 0.0437(8) Uani 1 1 d . . . . .
H6 H 0.189644 0.384222 -0.050360 0.052 Uiso 1 1 calc R U . . .
C7 C 0.21123(18) 0.49154(18) -0.08149(15) 0.0498(9) Uani 1 1 d . . . . .
H7 H 0.254004 0.506103 -0.107826 0.060 Uiso 1 1 calc R U . . .
C8 C 0.17861(18) 0.53523(19) -0.07170(16) 0.0507(9) Uani 1 1 d . . . . .
H8 H 0.195624 0.583576 -0.090613 0.061 Uiso 1 1 calc R U . . .
C9 C 0.0392(2) 0.16159(18) 0.08925(17) 0.0586(10) Uani 1 1 d . . . . .
H9A H 0.057256 0.145220 0.053481 0.088 Uiso 1 1 calc R U . . .
H9B H -0.005352 0.117171 0.107389 0.088 Uiso 1 1 calc R U . . .
H9C H 0.080108 0.184836 0.120137 0.088 Uiso 1 1 calc R U . . .
C10 C 0.00260(16) 0.41038(16) 0.18331(14) 0.0384(7) Uani 1 1 d . . . . .
C11 C 0.03191(17) 0.39659(17) 0.23622(14) 0.0409(7) Uani 1 1 d . . . . .
H11 H 0.007266 0.347124 0.254409 0.049 Uiso 1 1 calc R U . . .
C12 C 0.09704(18) 0.45493(18) 0.26243(15) 0.0441(8) Uani 1 1 d . . . . .
H12 H 0.117018 0.445507 0.299046 0.053 Uiso 1 1 calc R U . . .
C13 C 0.13407(17) 0.52736(17) 0.23627(15) 0.0417(8) Uani 1 1 d . . . . .
C14 C 0.10245(18) 0.54051(17) 0.18426(15) 0.0443(8) Uani 1 1 d . . . . .
H14 H 0.126035 0.590404 0.166903 0.053 Uiso 1 1 calc R U . . .
C15 C 0.03750(17) 0.48275(17) 0.15716(14) 0.0420(8) Uani 1 1 d . . . . .
H15 H 0.016861 0.492341 0.121026 0.050 Uiso 1 1 calc R U . . .
C16 C 0.20805(17) 0.59004(19) 0.26218(16) 0.0577(10) Uani 1 1 d . . . . .
H16A H 0.203523 0.635454 0.269938 0.087 Uiso 1 1 calc R U . . .
H16B H 0.249378 0.602715 0.232484 0.087 Uiso 1 1 calc R U . . .
H16C H 0.219531 0.572867 0.301044 0.087 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 C2 1.417(3) . ?
S1 O1 1.428(2) . ?
S1 O2 1.428(2) . ?
S1 N2 1.662(2) . ?
S1 C10 1.760(3) . ?
S3 C8 1.712(3) . ?
S3 C5 1.731(3) . ?
N1 C4 1.293(3) . ?
N1 N2 1.397(3) . ?
N2 C1 1.464(3) . ?
C1 C2 1.507(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.506(4) . ?
C2 C9 1.512(4) . ?
C3 C4 1.502(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.450(4) . ?
C5 C6 1.369(4) . ?
C6 C7 1.414(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.355(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.379(4) . ?
C10 C15 1.386(4) . ?
C11 C12 1.374(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(4) . ?
C13 C16 1.502(4) . ?
C14 C15 1.376(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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 120.17(13) . . ?
O1 S1 N2 105.62(13) . . ?
O2 S1 N2 106.64(13) . . ?
O1 S1 C10 110.01(14) . . ?
O2 S1 C10 108.53(13) . . ?
N2 S1 C10 104.72(13) . . ?
C8 S3 C5 91.42(15) . . ?
C4 N1 N2 118.7(2) . . ?
N1 N2 C1 118.4(2) . . ?
N1 N2 S1 108.80(18) . . ?
C1 N2 S1 118.2(2) . . ?
N2 C1 C2 108.8(2) . . ?
N2 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
N2 C1 H1B 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
F1 C2 C3 106.7(3) . . ?
F1 C2 C1 106.2(2) . . ?
C3 C2 C1 110.4(2) . . ?
F1 C2 C9 107.3(2) . . ?
C3 C2 C9 113.1(3) . . ?
C1 C2 C9 112.7(3) . . ?
C4 C3 C2 112.6(3) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
N1 C4 C5 116.3(3) . . ?
N1 C4 C3 125.3(3) . . ?
C5 C4 C3 118.5(3) . . ?
C6 C5 C4 127.9(3) . . ?
C6 C5 S3 111.0(2) . . ?
C4 C5 S3 121.1(2) . . ?
C5 C6 C7 112.7(3) . . ?
C5 C6 H6 123.7 . . ?
C7 C6 H6 123.7 . . ?
C8 C7 C6 112.7(3) . . ?
C8 C7 H7 123.7 . . ?
C6 C7 H7 123.7 . . ?
C7 C8 S3 112.2(3) . . ?
C7 C8 H8 123.9 . . ?
S3 C8 H8 123.9 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 120.5(3) . . ?
C11 C10 S1 119.7(2) . . ?
C15 C10 S1 119.6(2) . . ?
C12 C11 C10 119.5(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 118.5(3) . . ?
C14 C13 C16 120.1(3) . . ?
C12 C13 C16 121.4(3) . . ?
C15 C14 C13 121.3(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C10 119.1(3) . . ?
C14 C15 H15 120.5 . . ?
C10 C15 H15 120.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C4 N1 N2 C1 21.7(4) . . . . ?
C4 N1 N2 S1 160.4(2) . . . . ?
O1 S1 N2 N1 -174.75(17) . . . . ?
O2 S1 N2 N1 56.3(2) . . . . ?
C10 S1 N2 N1 -58.6(2) . . . . ?
O1 S1 N2 C1 -35.9(2) . . . . ?
O2 S1 N2 C1 -164.8(2) . . . . ?
C10 S1 N2 C1 80.2(2) . . . . ?
N1 N2 C1 C2 -50.3(3) . . . . ?
S1 N2 C1 C2 174.8(2) . . . . ?
N2 C1 C2 F1 -58.8(3) . . . . ?
N2 C1 C2 C3 56.5(3) . . . . ?
N2 C1 C2 C9 -176.0(3) . . . . ?
F1 C2 C3 C4 77.7(3) . . . . ?
C1 C2 C3 C4 -37.3(4) . . . . ?
C9 C2 C3 C4 -164.6(3) . . . . ?
N2 N1 C4 C5 -179.7(2) . . . . ?
N2 N1 C4 C3 0.2(4) . . . . ?
C2 C3 C4 N1 9.1(4) . . . . ?
C2 C3 C4 C5 -171.1(3) . . . . ?
N1 C4 C5 C6 180.0(3) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
N1 C4 C5 S3 -0.3(4) . . . . ?
C3 C4 C5 S3 179.9(2) . . . . ?
C8 S3 C5 C6 -0.7(2) . . . . ?
C8 S3 C5 C4 179.5(3) . . . . ?
C4 C5 C6 C7 -179.0(3) . . . . ?
S3 C5 C6 C7 1.2(3) . . . . ?
C5 C6 C7 C8 -1.1(4) . . . . ?
C6 C7 C8 S3 0.5(4) . . . . ?
C5 S3 C8 C7 0.1(3) . . . . ?
O1 S1 C10 C11 25.2(3) . . . . ?
O2 S1 C10 C11 158.5(2) . . . . ?
N2 S1 C10 C11 -87.9(3) . . . . ?
O1 S1 C10 C15 -159.8(2) . . . . ?
O2 S1 C10 C15 -26.5(3) . . . . ?
N2 S1 C10 C15 87.1(2) . . . . ?
C15 C10 C11 C12 -1.2(4) . . . . ?
S1 C10 C11 C12 173.7(2) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C11 C12 C13 C14 2.3(4) . . . . ?
C11 C12 C13 C16 -175.9(3) . . . . ?
C12 C13 C14 C15 -2.6(4) . . . . ?
C16 C13 C14 C15 175.6(3) . . . . ?
C13 C14 C15 C10 1.1(4) . . . . ?
C11 C10 C15 C14 0.8(4) . . . . ?
S1 C10 C15 C14 -174.1(2) . . . . ?

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_18004
_database_code_depnum_ccdc_archive 'CCDC 2083053'
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2021-07-06 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         'C12 H14 F N O'
_chemical_formula_sum            'C12 H14 F N O'
_chemical_formula_weight         207.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
F F 0.0171 0.0103 '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                   9.348(5)
_cell_length_b                   8.856(5)
_cell_length_c                   25.174(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2084.1(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    787
_cell_measurement_theta_min      2.714
_cell_measurement_theta_max      27.141

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.301
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   
;
absoprtion correction based on 4961 reflections(SADABS);Rint 0.1220 before
correction and 0.0954 after.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14961
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_av_R_equivalents  0.1179
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.618
_diffrn_reflns_theta_max         25.990
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2047
_reflns_number_gt                1557
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0967P)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_number_reflns         2047
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1565
_refine_ls_wR_factor_gt          0.1462
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.55012(12) 0.98973(12) 0.56643(5) 0.0312(4) Uani 1 1 d . . . . .
O1 O 0.26655(15) 1.03063(15) 0.58727(5) 0.0306(4) Uani 1 1 d . . . . .
N1 N 0.27854(18) 1.01384(18) 0.64337(6) 0.0270(4) Uani 1 1 d . . . . .
C1 C 0.3139(2) 0.9069(2) 0.55586(8) 0.0269(5) Uani 1 1 d . . . . .
H1A H 0.312181 0.935958 0.517894 0.032 Uiso 1 1 calc R U . . .
H1B H 0.247562 0.820754 0.560666 0.032 Uiso 1 1 calc R U . . .
C2 C 0.4626(2) 0.8590(2) 0.57088(7) 0.0240(5) Uani 1 1 d . . . . .
C3 C 0.4619(2) 0.8150(2) 0.62873(7) 0.0228(5) Uani 1 1 d . . . . .
H3A H 0.429275 0.709021 0.632047 0.027 Uiso 1 1 calc R U . . .
H3B H 0.560622 0.820843 0.642793 0.027 Uiso 1 1 calc R U . . .
C4 C 0.36610(19) 0.9149(2) 0.66147(7) 0.0202(4) Uani 1 1 d . . . . .
C5 C 0.3733(2) 0.9042(2) 0.72031(7) 0.0198(5) Uani 1 1 d . . . . .
C6 C 0.4680(2) 0.8055(2) 0.74471(8) 0.0233(5) Uani 1 1 d . . . . .
H6 H 0.527762 0.743040 0.723509 0.028 Uiso 1 1 calc R U . . .
C7 C 0.4767(2) 0.7967(2) 0.79967(8) 0.0255(5) Uani 1 1 d . . . . .
H7 H 0.542937 0.728817 0.815440 0.031 Uiso 1 1 calc R U . . .
C8 C 0.3907(2) 0.8850(2) 0.83197(7) 0.0233(5) Uani 1 1 d . . . . .
C9 C 0.2956(2) 0.9828(2) 0.80753(8) 0.0257(5) Uani 1 1 d . . . . .
H9 H 0.235624 1.044726 0.828817 0.031 Uiso 1 1 calc R U . . .
C10 C 0.2861(2) 0.9921(2) 0.75278(8) 0.0246(5) Uani 1 1 d . . . . .
H10 H 0.219131 1.059404 0.737120 0.030 Uiso 1 1 calc R U . . .
C11 C 0.5226(2) 0.7416(2) 0.53412(8) 0.0336(6) Uani 1 1 d . . . . .
H11A H 0.528539 0.782996 0.498078 0.050 Uiso 1 1 calc R U . . .
H11B H 0.460141 0.652788 0.534105 0.050 Uiso 1 1 calc R U . . .
H11C H 0.618415 0.712509 0.546167 0.050 Uiso 1 1 calc R U . . .
C12 C 0.4028(2) 0.8731(3) 0.89149(8) 0.0327(5) Uani 1 1 d . . . . .
H12A H 0.400723 0.766598 0.901970 0.049 Uiso 1 1 calc R U . . .
H12B H 0.322567 0.926422 0.908100 0.049 Uiso 1 1 calc R U . . .
H12C H 0.493078 0.918713 0.903129 0.049 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 C2 1.422(2) . ?
O1 C1 1.422(2) . ?
O1 N1 1.425(2) . ?
N1 C4 1.283(2) . ?
C1 C2 1.502(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C11 1.500(3) . ?
C2 C3 1.507(3) . ?
C3 C4 1.505(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.486(3) . ?
C5 C6 1.387(3) . ?
C5 C10 1.393(3) . ?
C6 C7 1.388(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.385(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(3) . ?
C8 C12 1.506(3) . ?
C9 C10 1.384(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C1 O1 N1 116.51(13) . . ?
C4 N1 O1 118.27(16) . . ?
O1 C1 C2 111.44(16) . . ?
O1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
O1 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
F1 C2 C11 107.46(16) . . ?
F1 C2 C1 106.43(16) . . ?
C11 C2 C1 112.74(17) . . ?
F1 C2 C3 106.80(15) . . ?
C11 C2 C3 114.73(17) . . ?
C1 C2 C3 108.19(15) . . ?
C4 C3 C2 112.31(16) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
N1 C4 C5 115.26(17) . . ?
N1 C4 C3 125.94(17) . . ?
C5 C4 C3 118.78(16) . . ?
C6 C5 C10 117.78(18) . . ?
C6 C5 C4 120.70(17) . . ?
C10 C5 C4 121.52(17) . . ?
C5 C6 C7 120.92(18) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 121.31(18) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 117.68(18) . . ?
C7 C8 C12 120.07(18) . . ?
C9 C8 C12 122.24(18) . . ?
C10 C9 C8 121.40(18) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C5 120.91(18) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C1 O1 N1 C4 20.4(2) . . . . ?
N1 O1 C1 C2 -51.8(2) . . . . ?
O1 C1 C2 F1 -55.3(2) . . . . ?
O1 C1 C2 C11 -172.86(16) . . . . ?
O1 C1 C2 C3 59.2(2) . . . . ?
F1 C2 C3 C4 76.74(19) . . . . ?
C11 C2 C3 C4 -164.30(16) . . . . ?
C1 C2 C3 C4 -37.5(2) . . . . ?
O1 N1 C4 C5 179.77(14) . . . . ?
O1 N1 C4 C3 1.5(3) . . . . ?
C2 C3 C4 N1 9.0(3) . . . . ?
C2 C3 C4 C5 -169.23(15) . . . . ?
N1 C4 C5 C6 -177.50(17) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
N1 C4 C5 C10 2.5(3) . . . . ?
C3 C4 C5 C10 -179.11(16) . . . . ?
C10 C5 C6 C7 -1.0(3) . . . . ?
C4 C5 C6 C7 179.01(17) . . . . ?
C5 C6 C7 C8 0.5(3) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C6 C7 C8 C12 -179.88(18) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C12 C8 C9 C10 179.97(18) . . . . ?
C8 C9 C10 C5 -0.7(3) . . . . ?
C6 C5 C10 C9 1.0(3) . . . . ?
C4 C5 C10 C9 -178.92(17) . . . . ?

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_18064
_database_code_depnum_ccdc_archive 'CCDC 2083054'
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2021-07-06 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         'C18 H18 Cl F N2 O2 S'
_chemical_formula_sum            'C18 H18 Cl F N2 O2 S'
_chemical_formula_weight         380.85

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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.028(3)
_cell_length_b                   9.215(3)
_cell_length_c                   17.393(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.322(5)
_cell_angle_gamma                90
_cell_volume                     1748.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    857
_cell_measurement_theta_min      2.895
_cell_measurement_theta_max      27.103

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.362
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.717
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_process_details   
;
absoprtion correction based on 7587 reflections(SADABS);Rint 0.1022 before
correction and 0.0328 after.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13028
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.060
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3445
_reflns_number_gt                2945
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0593P)²+0.4928P] 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         3445
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.53934(5) 0.20179(7) -0.08686(4) 0.04496(19) Uani 1 1 d . . . . .
F1 F 0.31734(11) 0.71341(12) 0.29803(7) 0.0328(3) Uani 1 1 d . . . . .
S1 S -0.02081(4) 0.61828(5) 0.15992(3) 0.02120(14) Uani 1 1 d . . . . .
O1 O -0.07397(12) 0.68581(16) 0.22124(8) 0.0284(3) Uani 1 1 d . . . . .
O2 O -0.02790(12) 0.68759(15) 0.08643(8) 0.0254(3) Uani 1 1 d . . . . .
N1 N 0.19032(14) 0.53959(17) 0.13830(9) 0.0203(3) Uani 1 1 d . . . . .
N2 N 0.12758(14) 0.60237(17) 0.19476(9) 0.0214(4) Uani 1 1 d . . . . .
C1 C 0.15642(17) 0.5458(2) 0.27445(10) 0.0239(4) Uani 1 1 d . . . . .
H1A H 0.132963 0.442190 0.275849 0.029 Uiso 1 1 calc R U . . .
H1B H 0.110269 0.600423 0.309749 0.029 Uiso 1 1 calc R U . . .
C2 C 0.29214(18) 0.5624(2) 0.30001(11) 0.0245(4) Uani 1 1 d . . . . .
C3 C 0.36365(17) 0.4905(2) 0.24266(11) 0.0244(4) Uani 1 1 d . . . . .
H3A H 0.442680 0.541832 0.243522 0.029 Uiso 1 1 calc R U . . .
H3B H 0.382046 0.389228 0.259490 0.029 Uiso 1 1 calc R U . . .
C4 C 0.29778(16) 0.4891(2) 0.16082(11) 0.0201(4) Uani 1 1 d . . . . .
C5 C 0.35918(17) 0.4189(2) 0.09975(11) 0.0213(4) Uani 1 1 d . . . . .
C6 C 0.48300(18) 0.3856(2) 0.11211(12) 0.0293(5) Uani 1 1 d . . . . .
H6 H 0.530251 0.408826 0.160640 0.035 Uiso 1 1 calc R U . . .
C7 C 0.53919(19) 0.3194(3) 0.05535(13) 0.0338(5) Uani 1 1 d . . . . .
H7 H 0.624232 0.297445 0.064440 0.041 Uiso 1 1 calc R U . . .
C8 C 0.46963(19) 0.2857(2) -0.01468(12) 0.0291(5) Uani 1 1 d . . . . .
C9 C 0.34630(19) 0.3164(2) -0.02881(12) 0.0302(5) Uani 1 1 d . . . . .
H9 H 0.299520 0.292341 -0.077378 0.036 Uiso 1 1 calc R U . . .
C10 C 0.29152(18) 0.3823(2) 0.02842(11) 0.0265(4) Uani 1 1 d . . . . .
H10 H 0.206288 0.403157 0.019090 0.032 Uiso 1 1 calc R U . . .
C11 C 0.3290(2) 0.5107(3) 0.38207(12) 0.0334(5) Uani 1 1 d . . . . .
H11A H 0.417453 0.523939 0.396959 0.050 Uiso 1 1 calc R U . . .
H11B H 0.308562 0.407635 0.385574 0.050 Uiso 1 1 calc R U . . .
H11C H 0.285000 0.566783 0.417138 0.050 Uiso 1 1 calc R U . . .
C12 C -0.07824(16) 0.4411(2) 0.14697(11) 0.0215(4) Uani 1 1 d . . . . .
C13 C -0.12515(18) 0.3728(2) 0.20732(12) 0.0282(5) Uani 1 1 d . . . . .
H13 H -0.128744 0.422675 0.254741 0.034 Uiso 1 1 calc R U . . .
C14 C -0.16653(19) 0.2318(2) 0.19788(13) 0.0310(5) Uani 1 1 d . . . . .
H14 H -0.198697 0.184863 0.239162 0.037 Uiso 1 1 calc R U . . .
C15 C -0.16190(17) 0.1573(2) 0.12875(12) 0.0268(4) Uani 1 1 d . . . . .
C16 C -0.11378(18) 0.2279(2) 0.06938(12) 0.0275(5) Uani 1 1 d . . . . .
H16 H -0.109732 0.178312 0.021948 0.033 Uiso 1 1 calc R U . . .
C17 C -0.07187(18) 0.3686(2) 0.07802(11) 0.0241(4) Uani 1 1 d . . . . .
H17 H -0.038879 0.415413 0.037006 0.029 Uiso 1 1 calc R U . . .
C18 C -0.2089(2) 0.0043(2) 0.11771(15) 0.0401(6) Uani 1 1 d . . . . .
H18A H -0.188142 -0.049826 0.166351 0.060 Uiso 1 1 calc R U . . .
H18B H -0.171074 -0.042893 0.076607 0.060 Uiso 1 1 calc R U . . .
H18C H -0.298098 0.005866 0.103001 0.060 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C8 1.745(2) . ?
F1 C2 1.420(2) . ?
S1 O2 1.4210(14) . ?
S1 O1 1.4315(14) . ?
S1 N2 1.6671(17) . ?
S1 C12 1.754(2) . ?
N1 C4 1.281(2) . ?
N1 N2 1.405(2) . ?
N2 C1 1.472(2) . ?
C1 C2 1.506(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C11 1.504(3) . ?
C2 C3 1.511(3) . ?
C3 C4 1.502(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.488(3) . ?
C5 C6 1.386(3) . ?
C5 C10 1.394(3) . ?
C6 C7 1.381(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.378(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.376(3) . ?
C9 C10 1.378(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C17 1.383(3) . ?
C12 C13 1.387(3) . ?
C13 C14 1.379(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(3) . ?
C15 C18 1.505(3) . ?
C16 C17 1.377(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
O2 S1 O1 119.97(9) . . ?
O2 S1 N2 106.85(8) . . ?
O1 S1 N2 104.70(8) . . ?
O2 S1 C12 109.34(9) . . ?
O1 S1 C12 108.73(9) . . ?
N2 S1 C12 106.38(8) . . ?
C4 N1 N2 117.61(15) . . ?
N1 N2 C1 116.80(15) . . ?
N1 N2 S1 109.81(11) . . ?
C1 N2 S1 116.12(12) . . ?
N2 C1 C2 108.16(15) . . ?
N2 C1 H1A 110.1 . . ?
C2 C1 H1A 110.1 . . ?
N2 C1 H1B 110.1 . . ?
C2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
F1 C2 C11 107.86(16) . . ?
F1 C2 C1 106.40(15) . . ?
C11 C2 C1 111.61(16) . . ?
F1 C2 C3 106.93(15) . . ?
C11 C2 C3 113.08(17) . . ?
C1 C2 C3 110.58(15) . . ?
C4 C3 C2 113.73(16) . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
N1 C4 C5 115.87(17) . . ?
N1 C4 C3 125.87(17) . . ?
C5 C4 C3 118.22(16) . . ?
C6 C5 C10 118.24(18) . . ?
C6 C5 C4 121.72(17) . . ?
C10 C5 C4 120.03(17) . . ?
C7 C6 C5 121.39(19) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C8 C7 C6 118.77(19) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C9 C8 C7 121.42(19) . . ?
C9 C8 Cl1 119.30(17) . . ?
C7 C8 Cl1 119.28(16) . . ?
C8 C9 C10 119.12(19) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C5 121.04(19) . . ?
C9 C10 H10 119.5 . . ?
C5 C10 H10 119.5 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 120.57(18) . . ?
C17 C12 S1 119.87(15) . . ?
C13 C12 S1 119.50(15) . . ?
C14 C13 C12 119.38(19) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 121.00(19) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 118.44(19) . . ?
C16 C15 C18 120.39(19) . . ?
C14 C15 C18 121.16(19) . . ?
C17 C16 C15 121.23(19) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C12 119.38(18) . . ?
C16 C17 H17 120.3 . . ?
C12 C17 H17 120.3 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C4 N1 N2 C1 -29.3(2) . . . . ?
C4 N1 N2 S1 -164.20(14) . . . . ?
O2 S1 N2 N1 -50.46(14) . . . . ?
O1 S1 N2 N1 -178.71(12) . . . . ?
C12 S1 N2 N1 66.25(13) . . . . ?
O2 S1 N2 C1 174.26(13) . . . . ?
O1 S1 N2 C1 46.01(16) . . . . ?
C12 S1 N2 C1 -69.02(15) . . . . ?
N1 N2 C1 C2 57.1(2) . . . . ?
S1 N2 C1 C2 -170.81(13) . . . . ?
N2 C1 C2 F1 61.01(19) . . . . ?
N2 C1 C2 C11 178.43(17) . . . . ?
N2 C1 C2 C3 -54.8(2) . . . . ?
F1 C2 C3 C4 -85.92(19) . . . . ?
C11 C2 C3 C4 155.51(17) . . . . ?
C1 C2 C3 C4 29.5(2) . . . . ?
N2 N1 C4 C5 177.93(15) . . . . ?
N2 N1 C4 C3 0.1(3) . . . . ?
C2 C3 C4 N1 -1.3(3) . . . . ?
C2 C3 C4 C5 -179.15(16) . . . . ?
N1 C4 C5 C6 167.09(18) . . . . ?
C3 C4 C5 C6 -14.9(3) . . . . ?
N1 C4 C5 C10 -14.2(3) . . . . ?
C3 C4 C5 C10 163.83(18) . . . . ?
C10 C5 C6 C7 0.7(3) . . . . ?
C4 C5 C6 C7 179.5(2) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C6 C7 C8 Cl1 -179.90(17) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
Cl1 C8 C9 C10 179.83(16) . . . . ?
C8 C9 C10 C5 0.4(3) . . . . ?
C6 C5 C10 C9 -0.8(3) . . . . ?
C4 C5 C10 C9 -179.54(19) . . . . ?
O2 S1 C12 C17 27.67(18) . . . . ?
O1 S1 C12 C17 160.36(15) . . . . ?
N2 S1 C12 C17 -87.37(16) . . . . ?
O2 S1 C12 C13 -154.95(15) . . . . ?
O1 S1 C12 C13 -22.25(18) . . . . ?
N2 S1 C12 C13 90.02(16) . . . . ?
C17 C12 C13 C14 -0.5(3) . . . . ?
S1 C12 C13 C14 -177.89(16) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C13 C14 C15 C18 -179.0(2) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C18 C15 C16 C17 179.1(2) . . . . ?
C15 C16 C17 C12 -0.3(3) . . . . ?
C13 C12 C17 C16 0.7(3) . . . . ?
S1 C12 C17 C16 178.02(15) . . . . ?

_refine_diff_density_max         0.706
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_17126
_database_code_depnum_ccdc_archive 'CCDC 2083052'
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2021-07-06 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         'C11 H11 Cl F N O'
_chemical_formula_sum            'C11 H11 Cl F N O'
_chemical_formula_weight         227.66

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'
F F 0.0171 0.0103 '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'

_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                   9.503(6)
_cell_length_b                   9.161(6)
_cell_length_c                   24.001(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2090(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    577
_cell_measurement_theta_min      3.396
_cell_measurement_theta_max      22.964

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.350
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.163
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_process_details   
;
absoprtion correction based on 2776 reflections(SADABS);Rint 0.1602 before
correction and 0.0923 after.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15005
_diffrn_reflns_av_unetI/netI     0.0895
_diffrn_reflns_av_R_equivalents  0.1739
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.697
_diffrn_reflns_theta_max         25.972
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2049
_reflns_number_gt                1272
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1185P)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_number_reflns         2049
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1401
_refine_ls_R_factor_gt           0.0865
_refine_ls_wR_factor_ref         0.2267
_refine_ls_wR_factor_gt          0.1974
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.09524(14) 0.08103(15) 0.43603(5) 0.0475(4) Uani 1 1 d . . . . .
F1 F -0.0218(3) -0.0473(3) 0.08372(12) 0.0470(8) Uani 1 1 d . . . . .
O1 O 0.2551(4) -0.0756(4) 0.11241(14) 0.0493(10) Uani 1 1 d . . . . .
N1 N 0.2325(4) -0.0614(5) 0.16979(16) 0.0414(10) Uani 1 1 d . . . . .
C1 C 0.2087(5) 0.0421(6) 0.0775(2) 0.0435(13) Uani 1 1 d . . . . .
H1A H 0.215545 0.012397 0.037970 0.052 Uiso 1 1 calc R U . . .
H1B H 0.270805 0.127670 0.083154 0.052 Uiso 1 1 calc R U . . .
C2 C 0.0585(5) 0.0841(5) 0.0908(2) 0.0401(12) Uani 1 1 d . . . . .
C3 C 0.0487(5) 0.1253(5) 0.15099(19) 0.0367(11) Uani 1 1 d . . . . .
H3A H -0.050277 0.116192 0.163390 0.044 Uiso 1 1 calc R U . . .
H3B H 0.076989 0.228699 0.155401 0.044 Uiso 1 1 calc R U . . .
C4 C 0.1408(5) 0.0310(5) 0.1874(2) 0.0350(11) Uani 1 1 d . . . . .
C5 C 0.1268(5) 0.0399(5) 0.24820(19) 0.0335(11) Uani 1 1 d . . . . .
C6 C 0.0382(5) 0.1440(5) 0.2738(2) 0.0377(12) Uani 1 1 d . . . . .
H6 H -0.016213 0.207386 0.251048 0.045 Uiso 1 1 calc R U . . .
C7 C 0.0286(5) 0.1561(5) 0.3307(2) 0.0372(12) Uani 1 1 d . . . . .
H7 H -0.030859 0.227757 0.346980 0.045 Uiso 1 1 calc R U . . .
C8 C 0.1063(5) 0.0631(5) 0.3642(2) 0.0379(11) Uani 1 1 d . . . . .
C9 C 0.1914(5) -0.0427(6) 0.3405(2) 0.0417(12) Uani 1 1 d . . . . .
H9 H 0.242282 -0.108248 0.363611 0.050 Uiso 1 1 calc R U . . .
C10 C 0.2022(5) -0.0526(5) 0.2841(2) 0.0393(12) Uani 1 1 d . . . . .
H10 H 0.262657 -0.124426 0.268476 0.047 Uiso 1 1 calc R U . . .
C11 C -0.0023(6) 0.1944(6) 0.0513(2) 0.0457(13) Uani 1 1 d . . . . .
H11A H 0.006091 0.158268 0.012976 0.069 Uiso 1 1 calc R U . . .
H11B H 0.049137 0.286651 0.054856 0.069 Uiso 1 1 calc R U . . .
H11C H -0.101740 0.210321 0.060181 0.069 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C8 1.735(5) . ?
F1 C2 1.435(5) . ?
O1 N1 1.400(5) . ?
O1 C1 1.435(6) . ?
N1 C4 1.287(6) . ?
C1 C2 1.512(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.497(7) . ?
C2 C11 1.501(7) . ?
C3 C4 1.509(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.467(6) . ?
C5 C10 1.405(7) . ?
C5 C6 1.413(7) . ?
C6 C7 1.373(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.384(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(7) . ?
C9 C10 1.361(7) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
N1 O1 C1 117.2(4) . . ?
C4 N1 O1 119.2(4) . . ?
O1 C1 C2 111.0(4) . . ?
O1 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
F1 C2 C3 107.0(4) . . ?
F1 C2 C11 106.6(4) . . ?
C3 C2 C11 114.5(4) . . ?
F1 C2 C1 105.3(4) . . ?
C3 C2 C1 109.0(4) . . ?
C11 C2 C1 113.7(4) . . ?
C2 C3 C4 112.2(4) . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
N1 C4 C5 115.1(4) . . ?
N1 C4 C3 125.4(4) . . ?
C5 C4 C3 119.5(4) . . ?
C10 C5 C6 116.4(4) . . ?
C10 C5 C4 122.0(4) . . ?
C6 C5 C4 121.6(4) . . ?
C7 C6 C5 121.8(5) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C6 C7 C8 119.5(5) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C7 C8 C9 120.3(5) . . ?
C7 C8 Cl1 119.1(4) . . ?
C9 C8 Cl1 120.6(4) . . ?
C10 C9 C8 120.0(5) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C5 122.1(5) . . ?
C9 C10 H10 119.0 . . ?
C5 C10 H10 119.0 . . ?
C2 C11 H11A 109.5 . . ?
C2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
C1 O1 N1 C4 18.9(6) . . . . ?
N1 O1 C1 C2 -49.5(6) . . . . ?
O1 C1 C2 F1 -56.8(5) . . . . ?
O1 C1 C2 C3 57.8(5) . . . . ?
O1 C1 C2 C11 -173.1(4) . . . . ?
F1 C2 C3 C4 76.0(5) . . . . ?
C11 C2 C3 C4 -166.1(4) . . . . ?
C1 C2 C3 C4 -37.5(6) . . . . ?
O1 N1 C4 C5 -178.8(4) . . . . ?
O1 N1 C4 C3 2.2(7) . . . . ?
C2 C3 C4 N1 9.0(7) . . . . ?
C2 C3 C4 C5 -170.0(4) . . . . ?
N1 C4 C5 C10 -3.8(7) . . . . ?
C3 C4 C5 C10 175.3(4) . . . . ?
N1 C4 C5 C6 175.2(4) . . . . ?
C3 C4 C5 C6 -5.8(7) . . . . ?
C10 C5 C6 C7 1.3(7) . . . . ?
C4 C5 C6 C7 -177.7(4) . . . . ?
C5 C6 C7 C8 -0.8(7) . . . . ?
C6 C7 C8 C9 -0.9(7) . . . . ?
C6 C7 C8 Cl1 179.1(4) . . . . ?
C7 C8 C9 C10 2.0(7) . . . . ?
Cl1 C8 C9 C10 -178.1(4) . . . . ?
C8 C9 C10 C5 -1.3(8) . . . . ?
C6 C5 C10 C9 -0.3(7) . . . . ?
C4 C5 C10 C9 178.7(5) . . . . ?

_refine_diff_density_max         0.768
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.089

