# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_dm234
_audit_block_doi                 10.5517/ccdc.csd.cc1zkvn1
_database_code_depnum_ccdc_archive 'CCDC 1834414'
loop_
_audit_author_name
_audit_author_address
'Zhiming Lin'
;South China University of Technology
China
;
_audit_update_record             
;
2018-04-03 deposited with the CCDC.	2019-05-27 downloaded from the CCDC.
;
_audit_creation_date             2017-10-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 F2 N2 O2 S'
_chemical_formula_sum            'C16 H16 F2 N2 O2 S'
_chemical_formula_weight         338.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.8310(10)
_cell_length_b                   16.990(3)
_cell_length_c                   10.851(2)
_cell_angle_alpha                89.975(15)
_cell_angle_beta                 99.969(13)
_cell_angle_gamma                90.035(11)
_cell_volume                     1603.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    978
_cell_measurement_temperature    149.5(10)
_cell_measurement_theta_max      72.9960
_cell_measurement_theta_min      5.7000
_shelx_estimated_absorpt_T_max   0.818
_shelx_estimated_absorpt_T_min   0.745
_exptl_absorpt_coefficient_mu    2.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_av_unetI/netI     0.1043
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7440
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.965
_diffrn_reflns_theta_min         4.890
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.5(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     38.00  77.00   0.50    0.50    --    0.00  19.00 150.00   78
  2  ω     42.00  89.00   0.50    0.50    --    0.00  82.00-120.00   94
  3  ω    -64.00  15.00   0.50    0.50    --    0.00 -38.00  30.00  158
  4  ω     91.00 117.00   0.50    0.50    --   95.20 -15.00   0.00   52
  5  ω      6.00  79.00   0.50    0.50    --   95.20 -15.00   0.00  146
  6  ω     95.00 185.00   0.50    0.50    --   95.20  30.00 -30.00  180
  7  ω      6.00 116.00   0.50    0.50    --   95.20 -61.00   0.00  220
  8  ω      6.00 118.00   0.50    0.50    --   95.20 -77.00   0.00  224
  9  ω     80.00 115.00   0.50    0.50    --   95.20 -45.00  30.00   70
 10  ω     97.00 122.00   0.50    0.50    --   95.20 -77.00-120.00   50
 11  ω     72.00 173.00   0.50    0.50    --   95.20  15.00 -90.00  202
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0048279000
_diffrn_orient_matrix_UB_12      0.0561083000
_diffrn_orient_matrix_UB_13      0.1107463000
_diffrn_orient_matrix_UB_21      -0.0649350000
_diffrn_orient_matrix_UB_22      0.0656704000
_diffrn_orient_matrix_UB_23      -0.0920752000
_diffrn_orient_matrix_UB_31      -0.1647203000
_diffrn_orient_matrix_UB_32      -0.0275863000
_diffrn_orient_matrix_UB_33      0.0062160000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1813
_reflns_number_total             3066
_reflns_odcompleteness_completeness 98.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0629
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1175P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1695
_refine_ls_wR_factor_ref         0.2175
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C3(H3), C1(H1), C4(H4), C5(H5), C14(H14), C2(H2), C13(H13), C11(H11)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.22372(10) 0.24539(6) 0.22720(9) 0.0340(3) Uani 1 1 d . . . . .
F1 F 0.5802(2) 0.32500(15) 0.1213(2) 0.0496(7) Uani 1 1 d . . . . .
F2 F 0.3768(3) 0.39670(14) 0.1111(2) 0.0475(7) Uani 1 1 d . . . . .
O2 O 0.1955(3) 0.19970(16) 0.1155(3) 0.0393(7) Uani 1 1 d . . . . .
O1 O 0.2295(3) 0.20897(16) 0.3458(3) 0.0387(7) Uani 1 1 d . . . . .
N2 N 0.4001(3) 0.2825(2) 0.2306(3) 0.0343(8) Uani 1 1 d . . . . .
N1 N 0.4510(3) 0.3293(2) 0.3430(3) 0.0350(8) Uani 1 1 d . . . . .
C6 C 0.6410(4) 0.3545(2) 0.5165(4) 0.0343(9) Uani 1 1 d . . . . .
C7 C 0.5841(4) 0.3071(2) 0.4023(4) 0.0349(9) Uani 1 1 d . . . . .
C9 C 0.0917(4) 0.3231(2) 0.2139(4) 0.0334(9) Uani 1 1 d . . . . .
C16 C 0.4262(4) 0.3204(3) 0.1191(4) 0.0394(10) Uani 1 1 d . . . . .
H16 H 0.377011 0.290681 0.045515 0.047 Uiso 1 1 calc R . . . .
C10 C 0.0542(4) 0.3578(2) 0.3195(4) 0.0400(10) Uani 1 1 d . . . . .
H10 H 0.100983 0.340898 0.398512 0.048 Uiso 1 1 calc R . . . .
C3 C 0.7547(4) 0.4502(3) 0.7198(4) 0.0419(10) Uani 1 1 d . . . . .
H3 H 0.793017 0.482931 0.786645 0.050 Uiso 1 1 calc R . . . .
C1 C 0.7949(4) 0.3500(2) 0.5741(4) 0.0395(10) Uani 1 1 d . . . . .
H1 H 0.860413 0.314764 0.544092 0.047 Uiso 1 1 calc R . . . .
C4 C 0.6004(4) 0.4546(3) 0.6649(4) 0.0427(10) Uani 1 1 d . . . . .
H4 H 0.535056 0.489568 0.695611 0.051 Uiso 1 1 calc R . . . .
C12 C -0.1228(4) 0.4444(2) 0.1905(4) 0.0412(10) Uani 1 1 d . . . . .
C5 C 0.5454(4) 0.4068(2) 0.5649(4) 0.0389(10) Uani 1 1 d . . . . .
H5 H 0.442024 0.409588 0.528916 0.047 Uiso 1 1 calc R . . . .
C14 C 0.0250(4) 0.3500(3) 0.0958(4) 0.0406(10) Uani 1 1 d . . . . .
H14 H 0.052296 0.327665 0.024570 0.049 Uiso 1 1 calc R . . . .
C8 C 0.6799(4) 0.2414(2) 0.3680(4) 0.0398(10) Uani 1 1 d . . . . .
H8A H 0.618729 0.208586 0.306670 0.060 Uiso 1 1 calc GR . . . .
H8B H 0.718012 0.210786 0.441193 0.060 Uiso 1 1 calc GR . . . .
H8C H 0.764923 0.262419 0.334069 0.060 Uiso 1 1 calc GR . . . .
C2 C 0.8510(4) 0.3975(3) 0.6754(4) 0.0428(10) Uani 1 1 d . . . . .
H2 H 0.953495 0.393902 0.713501 0.051 Uiso 1 1 calc R . . . .
C13 C -0.0816(4) 0.4098(3) 0.0850(4) 0.0439(11) Uani 1 1 d . . . . .
H13 H -0.126612 0.427382 0.005959 0.053 Uiso 1 1 calc R . . . .
C11 C -0.0540(4) 0.4181(3) 0.3075(4) 0.0434(10) Uani 1 1 d . . . . .
H11 H -0.080142 0.440978 0.378821 0.052 Uiso 1 1 calc R . . . .
C15 C -0.2411(5) 0.5091(3) 0.1775(5) 0.0585(13) Uani 1 1 d . . . . .
H15A H -0.215665 0.548522 0.120962 0.088 Uiso 1 1 calc GR . . . .
H15B H -0.242426 0.532453 0.257850 0.088 Uiso 1 1 calc GR . . . .
H15C H -0.340711 0.487657 0.145274 0.088 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.424(3) . ?
S1 O1 1.421(3) . ?
S1 N2 1.675(3) . ?
S1 C9 1.751(4) . ?
F1 C16 1.358(4) . ?
F2 C16 1.366(5) . ?
N2 N1 1.460(4) . ?
N2 C16 1.424(5) . ?
N1 C7 1.294(4) . ?
C6 C7 1.490(5) . ?
C6 C1 1.396(5) . ?
C6 C5 1.391(5) . ?
C7 C8 1.487(5) . ?
C9 C10 1.379(5) . ?
C9 C14 1.392(6) . ?
C16 H16 0.9800 . ?
C10 H10 0.9300 . ?
C10 C11 1.392(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(5) . ?
C3 C2 1.377(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.385(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(6) . ?
C12 C13 1.390(6) . ?
C12 C11 1.383(6) . ?
C12 C15 1.507(6) . ?
C5 H5 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.377(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C2 H2 0.9300 . ?
C13 H13 0.9300 . ?
C11 H11 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
O2 S1 N2 104.44(16) . . ?
O2 S1 C9 108.97(17) . . ?
O1 S1 O2 120.46(18) . . ?
O1 S1 N2 104.84(15) . . ?
O1 S1 C9 108.75(18) . . ?
N2 S1 C9 108.77(17) . . ?
N1 N2 S1 112.0(2) . . ?
C16 N2 S1 115.9(2) . . ?
C16 N2 N1 113.1(3) . . ?
C7 N1 N2 112.2(3) . . ?
C1 C6 C7 120.3(3) . . ?
C5 C6 C7 121.4(3) . . ?
C5 C6 C1 118.2(4) . . ?
N1 C7 C6 113.7(3) . . ?
N1 C7 C8 127.0(4) . . ?
C8 C7 C6 119.3(3) . . ?
C10 C9 S1 120.5(3) . . ?
C10 C9 C14 120.0(4) . . ?
C14 C9 S1 119.5(3) . . ?
F1 C16 F2 104.8(3) . . ?
F1 C16 N2 108.6(3) . . ?
F1 C16 H16 110.2 . . ?
F2 C16 N2 112.6(3) . . ?
F2 C16 H16 110.2 . . ?
N2 C16 H16 110.2 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.8(4) . . ?
C11 C10 H10 120.1 . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(4) . . ?
C6 C1 H1 119.7 . . ?
C2 C1 C6 120.7(4) . . ?
C2 C1 H1 119.7 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.5(4) . . ?
C5 C4 H4 120.3 . . ?
C13 C12 C15 120.5(4) . . ?
C11 C12 C13 118.9(4) . . ?
C11 C12 C15 120.6(4) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 C6 121.4(4) . . ?
C4 C5 H5 119.3 . . ?
C9 C14 H14 120.2 . . ?
C13 C14 C9 119.7(4) . . ?
C13 C14 H14 120.2 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.0(4) . . ?
C14 C13 H13 119.5 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(4) . . ?
C12 C11 H11 119.7 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.307
_oxdiff_exptl_absorpt_empirical_full_min 0.462
# start Validation Reply Form
_vrf_PLAT138_dm234               
;
PROBLEM: Monoclinic: More than one Angle Unequal 90.0 ...     Please Check
RESPONSE: yes, we noticed it. Intrinsic symmetry suggests that the 
crystal belongs to be monoclinic with space group P21/c. 
;
# end Validation Reply Form
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_20181007-lzm-291_0m
_database_code_depnum_ccdc_archive 'CCDC 1888355'
loop_
_audit_author_name
_audit_author_address
'Yubing Huang' 'South China University of Technology'
_audit_update_record             
;
2019-01-03 deposited with the CCDC.	2019-05-27 downloaded from the CCDC.
;
_audit_creation_date             2018-10-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H22 F2 N2 O2 S'
_chemical_formula_sum            'C19 H22 F2 N2 O2 S'
_chemical_formula_weight         380.44
_chemical_absolute_configuration rm
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   13.066(3)
_cell_length_b                   12.853(3)
_cell_length_c                   11.974(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.841(6)
_cell_angle_gamma                90
_cell_volume                     2008.4(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2975
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.27
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0906 before and 0.0526 after correction. The Ratio of minimum to maximum transmission is 0.8940. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6388
_diffrn_reflns_point_group_measured_fraction_full 0.842
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.470
_diffrn_reflns_theta_min         2.224
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_full    0.701
_reflns_Friedel_fraction_max     0.686
_reflns_number_gt                2998
_reflns_number_total             3463
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 1046 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3463
_refine_ls_number_restraints     203
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0748P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1200
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C13(H13)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C15(H15), C7(H7), C6(H6), C3(H3), C19(H19), C16(H16), C18(H18),
 C17(H17)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C9(H9A,H9B,H9C), C1(H1A,H1B,H1C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.49473(7) 0.47942(6) 0.54517(7) 0.0445(2) Uani 1 1 d . U . . .
O1 O 0.5339(2) 0.4393(2) 0.4453(2) 0.0574(7) Uani 1 1 d . U . . .
F2 F 0.6452(2) 0.6680(3) 0.7300(2) 0.0860(9) Uani 1 1 d . U . . .
F1 F 0.4855(2) 0.6924(2) 0.6841(2) 0.0775(8) Uani 1 1 d . U . . .
O2 O 0.4835(2) 0.4147(2) 0.6405(3) 0.0641(8) Uani 1 1 d . U . . .
N2 N 0.5953(2) 0.6473(2) 0.5016(2) 0.0439(7) Uani 1 1 d . U . . .
N1 N 0.5790(2) 0.5708(2) 0.5889(2) 0.0440(7) Uani 1 1 d . U . . .
C8 C 0.6861(3) 0.6449(3) 0.4664(3) 0.0425(7) Uani 1 1 d . U . . .
C4 C 0.3582(3) 0.5844(3) 0.4077(3) 0.0526(9) Uani 1 1 d . U . . .
H4 H 0.4096 0.5882 0.3569 0.063 Uiso 1 1 calc R . . . .
C14 C 0.7698(3) 0.5733(3) 0.5100(4) 0.0528(9) Uani 1 1 d . U . . .
C13 C 0.5592(3) 0.6183(3) 0.6934(3) 0.0567(10) Uani 1 1 d . U . . .
H13 H 0.5406 0.5653 0.7476 0.068 Uiso 1 1 calc R . . . .
C5 C 0.3770(3) 0.5384(3) 0.5112(3) 0.0438(8) Uani 1 1 d . U . . .
C11 C 0.7080(3) 0.7229(3) 0.3738(3) 0.0534(9) Uani 1 1 d . U . . .
C15 C 0.8335(4) 0.6019(4) 0.6005(4) 0.0702(12) Uani 1 1 d . U . . .
H15 H 0.8244 0.6657 0.6354 0.084 Uiso 1 1 calc R . . . .
C7 C 0.2046(3) 0.5736(4) 0.5574(4) 0.0627(11) Uani 1 1 d . U . . .
H7 H 0.1531 0.5703 0.6082 0.075 Uiso 1 1 calc R . . . .
C2 C 0.1833(3) 0.6188(3) 0.4534(4) 0.0629(11) Uani 1 1 d . U . . .
C6 C 0.2994(3) 0.5338(3) 0.5872(3) 0.0550(9) Uani 1 1 d . U . . .
H6 H 0.3120 0.5041 0.6574 0.066 Uiso 1 1 calc R . . . .
C3 C 0.2622(3) 0.6244(4) 0.3808(4) 0.0636(11) Uani 1 1 d . U . . .
H3 H 0.2501 0.6562 0.3117 0.076 Uiso 1 1 calc R . . . .
C19 C 0.7842(4) 0.4785(3) 0.4603(5) 0.0731(13) Uani 1 1 d . U . . .
H19 H 0.7424 0.4573 0.3994 0.088 Uiso 1 1 calc R . . . .
C16 C 0.9114(4) 0.5349(6) 0.6395(6) 0.0883(16) Uani 1 1 d . U . . .
H16 H 0.9544 0.5543 0.7002 0.106 Uiso 1 1 calc R . . . .
C18 C 0.8636(5) 0.4141(4) 0.5035(7) 0.0944(18) Uani 1 1 d . U . . .
H18 H 0.8736 0.3495 0.4707 0.113 Uiso 1 1 calc R . . . .
C12 C 0.7989(6) 0.7897(5) 0.4118(7) 0.104(2) Uani 1 1 d . U . . .
H12A H 0.7836 0.8258 0.4791 0.155 Uiso 1 1 calc GR . . . .
H12B H 0.8126 0.8393 0.3545 0.155 Uiso 1 1 calc GR . . . .
H12C H 0.8579 0.7463 0.4257 0.155 Uiso 1 1 calc GR . . . .
C17 C 0.9247(5) 0.4428(6) 0.5899(7) 0.0987(19) Uani 1 1 d . U . . .
H17 H 0.9770 0.3988 0.6162 0.118 Uiso 1 1 calc R . . . .
C9 C 0.7352(7) 0.6637(5) 0.2696(5) 0.106(2) Uani 1 1 d . U . . .
H9A H 0.7939 0.6205 0.2865 0.159 Uiso 1 1 calc GR . . . .
H9B H 0.7506 0.7122 0.2118 0.159 Uiso 1 1 calc GR . . . .
H9C H 0.6782 0.6210 0.2446 0.159 Uiso 1 1 calc GR . . . .
C1 C 0.0777(5) 0.6586(6) 0.4230(7) 0.110(2) Uani 1 1 d . U . . .
H1A H 0.0279 0.6096 0.4470 0.166 Uiso 1 1 calc GR . . . .
H1B H 0.0698 0.6674 0.3435 0.166 Uiso 1 1 calc GR . . . .
H1C H 0.0678 0.7242 0.4592 0.166 Uiso 1 1 calc GR . . . .
C10 C 0.6167(5) 0.7912(6) 0.3474(7) 0.123(3) Uani 1 1 d . U . . .
H10A H 0.5591 0.7489 0.3239 0.184 Uiso 1 1 calc GR . . . .
H10B H 0.6320 0.8386 0.2886 0.184 Uiso 1 1 calc GR . . . .
H10C H 0.6007 0.8299 0.4129 0.184 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.421(3) . ?
S1 O2 1.426(3) . ?
S1 N1 1.676(3) . ?
S1 C5 1.745(4) . ?
F2 C13 1.347(5) . ?
F1 C13 1.355(6) . ?
N2 N1 1.459(4) . ?
N2 C8 1.278(5) . ?
N1 C13 1.427(5) . ?
C8 C14 1.503(5) . ?
C8 C11 1.532(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(5) . ?
C4 C3 1.379(6) . ?
C14 C15 1.384(7) . ?
C14 C19 1.374(6) . ?
C13 H13 0.9800 . ?
C5 C6 1.396(5) . ?
C11 C12 1.517(7) . ?
C11 C9 1.518(7) . ?
C11 C10 1.503(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.396(8) . ?
C7 H7 0.9300 . ?
C7 C2 1.390(7) . ?
C7 C6 1.372(6) . ?
C2 C3 1.382(7) . ?
C2 C1 1.500(7) . ?
C6 H6 0.9300 . ?
C3 H3 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.405(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.339(10) . ?
C18 H18 0.9300 . ?
C18 C17 1.328(10) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C17 H17 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
O1 S1 O2 121.17(19) . . ?
O1 S1 N1 105.01(16) . . ?
O1 S1 C5 108.17(17) . . ?
O2 S1 N1 104.55(17) . . ?
O2 S1 C5 108.37(18) . . ?
N1 S1 C5 109.04(16) . . ?
C8 N2 N1 113.0(3) . . ?
N2 N1 S1 111.5(2) . . ?
C13 N1 S1 115.4(2) . . ?
C13 N1 N2 112.2(3) . . ?
N2 C8 C14 124.9(3) . . ?
N2 C8 C11 115.6(3) . . ?
C14 C8 C11 119.5(3) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.1(4) . . ?
C15 C14 C8 120.5(4) . . ?
C19 C14 C8 120.4(4) . . ?
C19 C14 C15 119.0(4) . . ?
F2 C13 F1 105.8(3) . . ?
F2 C13 N1 107.7(3) . . ?
F2 C13 H13 110.1 . . ?
F1 C13 N1 112.9(3) . . ?
F1 C13 H13 110.1 . . ?
N1 C13 H13 110.1 . . ?
C4 C5 S1 120.6(3) . . ?
C4 C5 C6 120.0(4) . . ?
C6 C5 S1 119.3(3) . . ?
C12 C11 C8 109.0(4) . . ?
C12 C11 C9 108.6(5) . . ?
C9 C11 C8 109.1(3) . . ?
C10 C11 C8 111.1(3) . . ?
C10 C11 C12 109.5(5) . . ?
C10 C11 C9 109.6(6) . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.9(5) . . ?
C16 C15 H15 120.1 . . ?
C2 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C6 C7 C2 121.8(4) . . ?
C7 C2 C1 120.0(5) . . ?
C3 C2 C7 117.6(4) . . ?
C3 C2 C1 122.4(5) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.4(4) . . ?
C7 C6 H6 120.3 . . ?
C4 C3 C2 122.1(4) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C14 C19 H19 120.7 . . ?
C14 C19 C18 118.6(6) . . ?
C18 C19 H19 120.7 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.4(6) . . ?
C17 C16 H16 119.8 . . ?
C19 C18 H18 119.1 . . ?
C17 C18 C19 121.8(6) . . ?
C17 C18 H18 119.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.3(6) . . ?
C18 C17 H17 119.8 . . ?
C11 C9 H9A 109.5 . . ?
C11 C9 H9B 109.5 . . ?
C11 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
