# 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. 
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data_y
_audit_block_doi                 10.5517/ccdc.csd.cc21hppy
_database_code_depnum_ccdc_archive 'CCDC 1891920'
loop_
_audit_author_name
_audit_author_address
'xiao geng'
;Central China Normal University
China
;
_audit_update_record             
;
2019-01-19 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_audit_creation_date             2019-01-18
_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         'C16 H9 F2 N O2'
_chemical_formula_sum            'C16 H9 F2 N O2'
_chemical_formula_weight         285.24
_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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5984(15)
_cell_length_b                   11.344(2)
_cell_length_c                   14.767(3)
_cell_angle_alpha                91.674(3)
_cell_angle_beta                 98.949(3)
_cell_angle_gamma                90.820(3)
_cell_volume                     1256.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2945
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.16
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
wR2(int) was 0.0899 before and 0.0426 after correction. 
The Ratio of minimum to maximum transmission is 0.8819. 
The λ/2 correction factor is 0.0015. 
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_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  0.0260
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7574
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        23.314
_diffrn_reflns_theta_max         23.314
_diffrn_reflns_theta_min         1.397
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2848
_reflns_number_total             3599
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       0.019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         3599
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.091
_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)+(0.1198P)²+0.0574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1437
_refine_ls_wR_factor_ref         0.1743
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups 
2.a Aromatic/amide H refined with riding coordinates: 
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C12(H12), C13(H13), C15(H15), 
 C16(H16), C18(H18), C19(H19), C21(H21), C22(H22), C25(H25), C28(H28), C29(H29), 
  C31(H31), C32(H32) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
C1 C 0.7175(4) 0.4617(3) 0.95390(16) 0.0552(7) Uani 1 1 d . . . . .
C2 C 0.7653(4) 0.3530(3) 0.92647(18) 0.0598(8) Uani 1 1 d . . . . .
H2 H 0.8408 0.3069 0.9659 0.072 Uiso 1 1 calc R . . . .
C3 C 0.6988(4) 0.3129(2) 0.83827(18) 0.0534(7) Uani 1 1 d . . . . .
H3 H 0.7303 0.2391 0.8178 0.064 Uiso 1 1 calc R . . . .
C4 C 0.5853(3) 0.3820(2) 0.78016(16) 0.0394(6) Uani 1 1 d . . . . .
C5 C 0.5377(3) 0.4911(2) 0.81186(17) 0.0483(6) Uani 1 1 d . . . . .
H5 H 0.4602 0.5378 0.7739 0.058 Uiso 1 1 calc R . . . .
C6 C 0.6049(4) 0.5305(2) 0.89932(17) 0.0559(7) Uani 1 1 d . . . . .
H6 H 0.5734 0.6038 0.9209 0.067 Uiso 1 1 calc R . . . .
C7 C 0.5292(3) 0.3343(2) 0.68503(16) 0.0397(6) Uani 1 1 d . . . . .
C8 C 0.4139(3) 0.40120(19) 0.61592(15) 0.0378(6) Uani 1 1 d . . . . .
C9 C 0.2509(3) 0.5181(2) 0.53396(16) 0.0439(6) Uani 1 1 d . . . . .
H9 H 0.1852 0.5840 0.5153 0.053 Uiso 1 1 calc R . . . .
C10 C 0.2726(3) 0.4242(2) 0.47974(15) 0.0384(6) Uani 1 1 d . . . . .
C11 C 0.2139(3) 0.38857(19) 0.38444(15) 0.0376(6) Uani 1 1 d . . . . .
C12 C 0.2752(3) 0.2862(2) 0.34781(17) 0.0465(6) Uani 1 1 d . . . . .
H12 H 0.3519 0.2382 0.3850 0.056 Uiso 1 1 calc R . . . .
C13 C 0.2232(3) 0.2550(2) 0.25666(18) 0.0506(7) Uani 1 1 d . . . . .
H13 H 0.2654 0.1868 0.2316 0.061 Uiso 1 1 calc R . . . .
C14 C 0.1091(3) 0.3258(2) 0.20415(16) 0.0477(6) Uani 1 1 d . . . . .
C15 C 0.0444(3) 0.4270(2) 0.23754(17) 0.0483(7) Uani 1 1 d . . . . .
H15 H -0.0335 0.4737 0.1998 0.058 Uiso 1 1 calc R . . . .
C16 C 0.0974(3) 0.4578(2) 0.32839(16) 0.0433(6) Uani 1 1 d . . . . .
H16 H 0.0544 0.5262 0.3526 0.052 Uiso 1 1 calc R . . . .
C17 C -0.1085(4) 0.8936(3) 0.10904(18) 0.0564(7) Uani 1 1 d . . . . .
C18 C -0.1693(4) 0.7916(3) 0.14131(19) 0.0574(7) Uani 1 1 d . . . . .
H18 H -0.2420 0.7389 0.1024 0.069 Uiso 1 1 calc R . . . .
C19 C -0.1208(3) 0.7689(2) 0.23208(18) 0.0492(7) Uani 1 1 d . . . . .
H19 H -0.1612 0.6997 0.2549 0.059 Uiso 1 1 calc R . . . .
C20 C -0.0125(3) 0.8469(2) 0.29086(16) 0.0419(6) Uani 1 1 d . . . . .
C21 C 0.0442(3) 0.9499(2) 0.25581(18) 0.0497(7) Uani 1 1 d . . . . .
H21 H 0.1151 1.0041 0.2942 0.060 Uiso 1 1 calc R . . . .
C22 C -0.0034(4) 0.9727(2) 0.16470(18) 0.0559(7) Uani 1 1 d . . . . .
H22 H 0.0358 1.0417 0.1411 0.067 Uiso 1 1 calc R . . . .
C23 C 0.0345(3) 0.8124(2) 0.38731(17) 0.0418(6) Uani 1 1 d . . . . .
C24 C 0.1469(3) 0.89020(19) 0.45645(16) 0.0394(6) Uani 1 1 d . . . . .
C25 C 0.2990(3) 1.0208(2) 0.53982(17) 0.0462(6) Uani 1 1 d . . . . .
H25 H 0.3601 1.0911 0.5585 0.055 Uiso 1 1 calc R . . . .
C26 C 0.2823(3) 0.9295(2) 0.59450(16) 0.0397(6) Uani 1 1 d . . . . .
C27 C 0.3361(3) 0.9051(2) 0.68995(16) 0.0414(6) Uani 1 1 d . . . . .
C28 C 0.2800(3) 0.8025(2) 0.72698(17) 0.0486(6) Uani 1 1 d . . . . .
H28 H 0.2115 0.7465 0.6892 0.058 Uiso 1 1 calc R . . . .
C29 C 0.3249(3) 0.7833(2) 0.81910(18) 0.0520(7) Uani 1 1 d . . . . .
H29 H 0.2873 0.7147 0.8440 0.062 Uiso 1 1 calc R . . . .
C30 C 0.4254(3) 0.8661(2) 0.87334(17) 0.0511(7) Uani 1 1 d . . . . .
C31 C 0.4864(4) 0.9668(2) 0.84003(18) 0.0546(7) Uani 1 1 d . . . . .
H31 H 0.5573 1.0208 0.8786 0.066 Uiso 1 1 calc R . . . .
C32 C 0.4409(3) 0.9869(2) 0.74806(18) 0.0484(6) Uani 1 1 d . . . . .
H32 H 0.4803 1.0557 0.7243 0.058 Uiso 1 1 calc R . . . .
F1 F 0.7849(2) 0.50166(17) 1.03917(10) 0.0819(6) Uani 1 1 d . . . . .
F2 F 0.0593(2) 0.29496(15) 0.11427(10) 0.0691(5) Uani 1 1 d . . . . .
F3 F 0.4665(2) 0.84640(17) 0.96420(10) 0.0767(6) Uani 1 1 d . . . . .
F4 F -0.1550(3) 0.91706(18) 0.01989(11) 0.0839(6) Uani 1 1 d . . . . .
N1 N 0.3399(3) 0.50269(17) 0.62098(13) 0.0439(5) Uani 1 1 d . . . . .
N2 N 0.2129(3) 0.99505(17) 0.45254(13) 0.0474(6) Uani 1 1 d . . . . .
O1 O 0.37851(19) 0.34768(13) 0.53218(10) 0.0405(4) Uani 1 1 d . . . . .
O2 O 0.5797(3) 0.23827(15) 0.66112(12) 0.0578(5) Uani 1 1 d . . . . .
O3 O -0.0141(2) 0.71900(14) 0.41259(12) 0.0562(5) Uani 1 1 d . . . . .
O4 O 0.1841(2) 0.84418(13) 0.54080(11) 0.0439(5) Uani 1 1 d . . . . .


_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
C1 C2 1.358(4) . ?
C1 C6 1.354(4) . ?
C1 F1 1.347(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(3) . ?
C4 C5 1.383(3) . ?
C4 C7 1.487(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.372(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.474(3) . ?
C7 O2 1.220(3) . ?
C8 N1 1.294(3) . ?
C8 O1 1.348(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.340(3) . ?
C9 N1 1.373(3) . ?
C10 C11 1.452(3) . ?
C10 O1 1.366(3) . ?
C11 C12 1.383(3) . ?
C11 C16 1.384(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.358(4) . ?
C14 C15 1.365(4) . ?
C14 F2 1.356(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.373(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.365(4) . ?
C17 C22 1.360(4) . ?
C17 F4 1.344(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.367(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.387(3) . ?
C20 C21 1.382(3) . ?
C20 C23 1.479(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.371(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.485(3) . ?
C23 O3 1.206(3) . ?
C24 N2 1.291(3) . ?
C24 O4 1.355(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.348(3) . ?
C25 N2 1.373(3) . ?
C26 C27 1.441(3) . ?
C26 O4 1.369(3) . ?
C27 C28 1.390(3) . ?
C27 C32 1.397(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.375(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.361(4) . ?
C30 C31 1.360(4) . ?
C30 F3 1.355(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.375(4) . ?
C32 H32 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.7(2) . . ?
F1 C1 C2 118.2(2) . . ?
F1 C1 C6 119.1(3) . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.2(2) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C7 116.5(2) . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 C7 124.3(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.4(3) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C8 C7 C4 121.6(2) . . ?
O2 C7 C4 120.8(2) . . ?
O2 C7 C8 117.6(2) . . ?
N1 C8 C7 131.6(2) . . ?
N1 C8 O1 113.75(19) . . ?
O1 C8 C7 114.7(2) . . ?
C10 C9 H9 124.9 . . ?
C10 C9 N1 110.2(2) . . ?
N1 C9 H9 124.9 . . ?
C9 C10 C11 136.2(2) . . ?
C9 C10 O1 107.0(2) . . ?
O1 C10 C11 116.8(2) . . ?
C12 C11 C10 120.8(2) . . ?
C12 C11 C16 118.9(2) . . ?
C16 C11 C10 120.2(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.7 . . ?
C14 C13 C12 118.6(2) . . ?
C14 C13 H13 120.7 . . ?
C13 C14 C15 122.9(2) . . ?
F2 C14 C13 118.4(2) . . ?
F2 C14 C15 118.7(2) . . ?
C14 C15 H15 120.9 . . ?
C14 C15 C16 118.1(2) . . ?
C16 C15 H15 120.9 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 121.0(2) . . ?
C15 C16 H16 119.5 . . ?
C22 C17 C18 121.9(3) . . ?
F4 C17 C18 119.1(3) . . ?
F4 C17 C22 119.0(3) . . ?
C17 C18 H18 120.8 . . ?
C17 C18 C19 118.5(3) . . ?
C19 C18 H18 120.8 . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.4(2) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C23 116.9(2) . . ?
C21 C20 C19 118.4(2) . . ?
C21 C20 C23 124.7(2) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.4(2) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 119.5(3) . . ?
C17 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C20 C23 C24 121.4(2) . . ?
O3 C23 C20 121.3(2) . . ?
O3 C23 C24 117.3(2) . . ?
N2 C24 C23 132.4(2) . . ?
N2 C24 O4 113.3(2) . . ?
O4 C24 C23 114.31(19) . . ?
C26 C25 H25 124.9 . . ?
C26 C25 N2 110.3(2) . . ?
N2 C25 H25 124.9 . . ?
C25 C26 C27 136.3(2) . . ?
C25 C26 O4 106.4(2) . . ?
O4 C26 C27 117.3(2) . . ?
C28 C27 C26 121.1(2) . . ?
C28 C27 C32 118.6(2) . . ?
C32 C27 C26 120.3(2) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.4(2) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 120.5 . . ?
C30 C29 C28 119.0(2) . . ?
C30 C29 H29 120.5 . . ?
C31 C30 C29 122.8(2) . . ?
F3 C30 C29 118.2(2) . . ?
F3 C30 C31 119.0(2) . . ?
C30 C31 H31 120.7 . . ?
C30 C31 C32 118.5(2) . . ?
C32 C31 H31 120.7 . . ?
C27 C32 H32 119.6 . . ?
C31 C32 C27 120.7(2) . . ?
C31 C32 H32 119.6 . . ?
C8 N1 C9 104.20(19) . . ?
C24 N2 C25 104.67(19) . . ?
C8 O1 C10 104.89(18) . . ?
C24 O4 C26 105.38(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 F2 0.93 2.54 3.367(3) 147.9 1_656
C9 H9 O3 0.93 2.54 3.422(3) 159.6 .
C15 H15 F1 0.93 2.58 3.403(3) 147.4 1_454
C25 H25 O2 0.93 2.62 3.500(3) 158.5 1_565

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 C2 C3 C4 -0.5(4) . . . . ?
C2 C1 C6 C5 -1.3(5) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C2 C3 C4 C7 176.5(2) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C3 C4 C7 C8 -177.9(2) . . . . ?
C3 C4 C7 O2 1.1(3) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C4 C7 C8 N1 -1.7(4) . . . . ?
C4 C7 C8 O1 178.33(18) . . . . ?
C5 C4 C7 C8 -0.7(3) . . . . ?
C5 C4 C7 O2 178.3(2) . . . . ?
C6 C1 C2 C3 1.5(5) . . . . ?
C7 C4 C5 C6 -176.0(2) . . . . ?
C7 C8 N1 C9 179.2(2) . . . . ?
C7 C8 O1 C10 -179.57(18) . . . . ?
C9 C10 C11 C12 174.5(3) . . . . ?
C9 C10 C11 C16 -4.6(4) . . . . ?
C9 C10 O1 C8 0.1(2) . . . . ?
C10 C9 N1 C8 0.8(3) . . . . ?
C10 C11 C12 C13 -178.0(2) . . . . ?
C10 C11 C16 C15 178.3(2) . . . . ?
C11 C10 O1 C8 179.76(18) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C12 C11 C16 C15 -0.8(4) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C12 C13 C14 F2 179.6(2) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C14 C15 C16 C11 0.3(4) . . . . ?
C16 C11 C12 C13 1.1(4) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C18 C17 C22 C21 0.3(4) . . . . ?
C18 C19 C20 C21 0.8(4) . . . . ?
C18 C19 C20 C23 -178.9(2) . . . . ?
C19 C20 C21 C22 -1.2(4) . . . . ?
C19 C20 C23 C24 -178.9(2) . . . . ?
C19 C20 C23 O3 2.5(3) . . . . ?
C20 C21 C22 C17 0.6(4) . . . . ?
C20 C23 C24 N2 4.6(4) . . . . ?
C20 C23 C24 O4 -177.46(18) . . . . ?
C21 C20 C23 C24 1.4(4) . . . . ?
C21 C20 C23 O3 -177.1(2) . . . . ?
C22 C17 C18 C19 -0.6(4) . . . . ?
C23 C20 C21 C22 178.5(2) . . . . ?
C23 C24 N2 C25 177.7(2) . . . . ?
C23 C24 O4 C26 -178.05(17) . . . . ?
C25 C26 C27 C28 173.4(3) . . . . ?
C25 C26 C27 C32 -4.1(4) . . . . ?
C25 C26 O4 C24 -0.3(2) . . . . ?
C26 C25 N2 C24 0.0(3) . . . . ?
C26 C27 C28 C29 -176.7(2) . . . . ?
C26 C27 C32 C31 177.1(2) . . . . ?
C27 C26 O4 C24 178.12(18) . . . . ?
C27 C28 C29 C30 -0.1(4) . . . . ?
C28 C27 C32 C31 -0.5(4) . . . . ?
C28 C29 C30 C31 -1.2(4) . . . . ?
C28 C29 C30 F3 179.1(2) . . . . ?
C29 C30 C31 C32 1.6(4) . . . . ?
C30 C31 C32 C27 -0.7(4) . . . . ?
C32 C27 C28 C29 0.9(4) . . . . ?
F1 C1 C2 C3 -178.8(2) . . . . ?
F1 C1 C6 C5 179.0(2) . . . . ?
F2 C14 C15 C16 -179.3(2) . . . . ?
F3 C30 C31 C32 -178.7(2) . . . . ?
F4 C17 C18 C19 180.0(2) . . . . ?
F4 C17 C22 C21 179.7(2) . . . . ?
N1 C8 O1 C10 0.4(2) . . . . ?
N1 C9 C10 C11 179.9(2) . . . . ?
N1 C9 C10 O1 -0.6(3) . . . . ?
N2 C24 O4 C26 0.3(3) . . . . ?
N2 C25 C26 C27 -177.8(2) . . . . ?
N2 C25 C26 O4 0.1(3) . . . . ?
O1 C8 N1 C9 -0.8(3) . . . . ?
O1 C10 C11 C12 -5.0(3) . . . . ?
O1 C10 C11 C16 176.0(2) . . . . ?
O2 C7 C8 N1 179.3(2) . . . . ?
O2 C7 C8 O1 -0.7(3) . . . . ?
O3 C23 C24 N2 -176.8(2) . . . . ?
O3 C23 C24 O4 1.2(3) . . . . ?
O4 C24 N2 C25 -0.2(3) . . . . ?
O4 C26 C27 C28 -4.3(3) . . . . ?
O4 C26 C27 C32 178.2(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_Y
_audit_block_doi                 10.5517/ccdc.csd.cc21r97c
_database_code_depnum_ccdc_archive 'CCDC 1899222'
loop_
_audit_author_name
_audit_author_address
'xiao geng'
;Central China Normal University
China
;
_audit_update_record             
;
2019-02-25 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H5 N O2 S'
_chemical_formula_weight         155.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.1602(12)
_cell_length_b                   7.5933(16)
_cell_length_c                   14.282(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     668.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4097
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      31.43

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ??
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.412
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7171
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.852
_diffrn_reflns_theta_max         32.125
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2193
_reflns_number_gt                2038
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.670
_reflns_Friedel_fraction_max     0.906
_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0865P)²+0.2129P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.045(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 788 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.13(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2193
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1505
_refine_ls_wR_factor_gt          0.1470
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_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
C1 C 0.9517(5) 0.8546(4) 0.2098(2) 0.0384(6) Uani 1 1 d . . . . .
H1 H 1.0775 0.7880 0.2033 0.046 Uiso 1 1 calc R U . . .
C2 C 0.8736(4) 0.9654(3) 0.14200(18) 0.0305(5) Uani 1 1 d . . . . .
C3 C 0.6788(5) 1.0505(4) 0.1691(2) 0.0390(6) Uani 1 1 d . . . . .
H3 H 0.6060 1.1300 0.1308 0.047 Uiso 1 1 calc R U . . .
C4 C 0.6025(5) 1.0023(4) 0.2625(2) 0.0380(6) Uani 1 1 d . . . . .
H4 H 0.4782 1.0424 0.2928 0.046 Uiso 1 1 calc R U . . .
C5 C 0.9827(4) 1.0072(3) 0.05417(18) 0.0285(5) Uani 1 1 d . . . . .
C6 C 1.1794(4) 0.8959(3) 0.02475(18) 0.0288(5) Uani 1 1 d . . . . .
N1 N 1.3234(4) 0.9830(3) -0.0265(2) 0.0418(6) Uani 1 1 d . . . . .
H1A H 1.4379 0.9303 -0.0466 0.050 Uiso 1 1 calc R U . . .
H1B H 1.3022 1.0922 -0.0397 0.050 Uiso 1 1 calc R U . . .
O1 O 0.9301(4) 1.1317(2) 0.00494(16) 0.0389(5) Uani 1 1 d . . . . .
O2 O 1.1982(4) 0.7410(2) 0.04630(16) 0.0366(5) Uani 1 1 d . . . . .
S1 S 0.79566(17) 0.85252(13) 0.30536(6) 0.0524(3) Uani 1 1 d . . . . .


_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
C1 C2 1.370(4) . ?
C1 S1 1.670(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.417(4) . ?
C2 C5 1.458(3) . ?
C3 C4 1.461(4) . ?
C3 H3 0.9300 . ?
C4 S1 1.756(3) . ?
C4 H4 0.9300 . ?
C5 O1 1.222(3) . ?
C5 C6 1.536(4) . ?
C6 O2 1.221(3) . ?
C6 N1 1.327(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?

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
C2 C1 S1 112.4(2) . . ?
C2 C1 H1 123.8 . . ?
S1 C1 H1 123.8 . . ?
C1 C2 C3 112.6(3) . . ?
C1 C2 C5 125.4(2) . . ?
C3 C2 C5 121.7(2) . . ?
C2 C3 C4 114.1(3) . . ?
C2 C3 H3 123.0 . . ?
C4 C3 H3 123.0 . . ?
C3 C4 S1 105.2(2) . . ?
C3 C4 H4 127.4 . . ?
S1 C4 H4 127.4 . . ?
O1 C5 C2 122.8(2) . . ?
O1 C5 C6 118.5(2) . . ?
C2 C5 C6 118.6(2) . . ?
O2 C6 N1 123.8(3) . . ?
O2 C6 C5 122.4(2) . . ?
N1 C6 C5 113.8(2) . . ?
C6 N1 H1A 120.0 . . ?
C6 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 S1 C4 95.70(15) . . ?

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
S1 C1 C2 C3 -0.4(3) . . . . ?
S1 C1 C2 C5 174.5(2) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C5 C2 C3 C4 -175.3(2) . . . . ?
C2 C3 C4 S1 0.6(3) . . . . ?
C1 C2 C5 O1 -164.8(3) . . . . ?
C3 C2 C5 O1 9.6(4) . . . . ?
C1 C2 C5 C6 12.0(4) . . . . ?
C3 C2 C5 C6 -173.6(2) . . . . ?
O1 C5 C6 O2 -152.7(3) . . . . ?
C2 C5 C6 O2 30.4(4) . . . . ?
O1 C5 C6 N1 26.5(4) . . . . ?
C2 C5 C6 N1 -150.4(2) . . . . ?
C2 C1 S1 C4 0.7(2) . . . . ?
C3 C4 S1 C1 -0.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 O2 0.93 2.39 2.915(4) 115.7 .
N1 H1A O2 0.86 2.07 2.882(3) 158.3 2_565
N1 H1B O1 0.86 2.29 3.014(3) 141.4 2_575

_refine_diff_density_max         0.538
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.075



