# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1(Br)
_database_code_depnum_ccdc_archive 'CCDC 2059486'
loop_
_audit_author_name
_audit_author_address
'zou hanxun'
;Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2021-01-29 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;
_audit_creation_date             2019-12-23
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_chemical_formula_moiety         'C14 H11 Br N2 O2'
_chemical_formula_sum            'C14 H11 Br N2 O2'
_chemical_formula_weight         319.159
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H -0.00002 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
C 0.01476 0.00704 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
Br -0.95016 1.04102 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
O 0.04121 0.02503 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
N 0.02530 0.01357 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   6.5158(1)
_cell_length_b                   9.5206(2)
_cell_length_c                   20.4243(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.165(2)
_cell_angle_gamma                90
_cell_volume                     1261.86(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173.15
_cell_measurement_reflns_used    8335
_cell_measurement_theta_min      3.7500
_cell_measurement_theta_max      60.2840
_exptl_absorpt_coefficient_mu    3.048
_exptl_absorpt_correction_type   none
_exptl_crystal_description       Prism
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_F_000             637.500
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.9965
_diffrn_reflns_Laue_measured_fraction_max 0.9691
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9319
_diffrn_reflns_point_group_measured_fraction_full 0.9965
_diffrn_reflns_point_group_measured_fraction_max 0.9691
_diffrn_reflns_theta_full        53.5942
_diffrn_reflns_theta_max         60.40
_diffrn_reflns_theta_min         3.78
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.9965
_diffrn_measured_fraction_theta_max 0.9691
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     1.34139
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                2676
_reflns_number_total             2788
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.4167
_refine_diff_density_min         -0.4087
_refine_diff_density_rms         0.0643
_refine_ls_d_res_high            0.7713
_refine_ls_d_res_low             10.1707
_refine_ls_goodness_of_fit_ref   1.0373
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2788
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0238
_refine_ls_restrained_S_all      1.0373
_refine_ls_shift/su_max          0.0991
_refine_ls_shift/su_mean         0.0009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0280P)²+1.2297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0615
_refine_ls_wR_factor_ref         0.0621
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), N7(H7), C9(H9), C13(H13), C15(H15), C16(H16), C18(H18), C19(H19),
 C20(H20)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
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_refinement_flags_posn
Br1 Br 0.04751(3) 0.07331(2) 0.263777(9) 0.02328(7) Uani 1.000000 .
O1 O 0.67591(17) 0.39424(12) 0.07269(6) 0.0152(2) Uani 1.000000 .
O2 O 0.15032(16) 0.64721(13) 0.04043(5) 0.0161(2) Uani 1.000000 .
H2 H 0.2109(3) 0.630(2) 0.0067(2) 0.0194(3) Uiso 1.000000 GR
C3 C 0.3404(2) 0.42082(16) 0.14198(8) 0.0135(3) Uani 1.000000 .
C4 C 0.6297(2) 0.76673(17) 0.06662(8) 0.0153(3) Uani 1.000000 .
C6 C 0.3737(3) 0.92252(18) 0.10377(9) 0.0201(3) Uani 1.000000 .
H6 H 0.2439(3) 0.93696(18) 0.12053(9) 0.0242(4) Uiso 1.000000 R
N7 N 0.6936(2) 0.62914(14) 0.05469(7) 0.0148(3) Uani 1.000000 .
H7 H 0.7985(2) 0.61729(14) 0.03095(7) 0.0178(3) Uiso 1.000000 R
C9 C 0.0559(2) 0.26810(17) 0.15912(8) 0.0168(3) Uani 1.000000 .
H9 H -0.0800(2) 0.23561(17) 0.14680(8) 0.0202(4) Uiso 1.000000 R
N10 N 0.4248(2) 0.53558(14) 0.10761(7) 0.0137(3) Uani 1.000000 .
C11 C 0.4366(2) 0.78676(17) 0.08943(8) 0.0153(3) Uani 1.000000 .
C12 C 0.1691(2) 0.21317(17) 0.21366(8) 0.0161(3) Uani 1.000000 .
C13 C 0.4519(3) 0.36425(19) 0.19681(8) 0.0188(3) Uani 1.000000 .
H13 H 0.5869(3) 0.39771(19) 0.20971(8) 0.0225(4) Uiso 1.000000 R
C14 C 0.6025(2) 0.51322(17) 0.07780(7) 0.0131(3) Uani 1.000000 .
C15 C 0.3673(3) 0.25927(19) 0.23279(8) 0.0200(3) Uani 1.000000 .
H15 H 0.4439(3) 0.21942(19) 0.27002(8) 0.0240(4) Uiso 1.000000 R
C16 C 0.1437(2) 0.37161(17) 0.12255(8) 0.0154(3) Uani 1.000000 .
H16 H 0.0692(2) 0.40864(17) 0.08429(8) 0.0185(4) Uiso 1.000000 R
C17 C 0.2987(2) 0.66220(17) 0.09568(8) 0.0143(3) Uani 1.000000 .
H17 H 0.2217(2) 0.67762(17) 0.13526(8) 0.0171(4) Uiso 1.000000 R
C18 C 0.4998(3) 1.03661(19) 0.09367(9) 0.0239(4) Uani 1.000000 .
H18 H 0.4567(3) 1.12898(19) 0.10350(9) 0.0287(4) Uiso 1.000000 R
C19 C 0.7569(3) 0.88056(19) 0.05621(8) 0.0198(3) Uani 1.000000 .
H19 H 0.8882(3) 0.86638(19) 0.04049(8) 0.0237(4) Uiso 1.000000 R
C20 C 0.6891(3) 1.01492(19) 0.06912(9) 0.0229(4) Uani 1.000000 .
H20 H 0.7735(3) 1.09330(19) 0.06105(9) 0.0275(4) Uiso 1.000000 R


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
Br1 C12 1.8961(16) . ?
O1 C14 1.238(2) . ?
O2 C17 1.4254(18) . ?
C3 N10 1.435(2) . ?
C3 C13 1.388(2) . ?
C3 C16 1.388(2) . ?
C4 N7 1.403(2) . ?
C4 C11 1.393(2) . ?
C4 C19 1.392(2) . ?
C6 C11 1.395(2) . ?
C6 C18 1.388(3) . ?
N7 C14 1.358(2) . ?
C9 C12 1.382(2) . ?
C9 C16 1.391(2) . ?
N10 C14 1.3723(19) . ?
N10 C17 1.467(2) . ?
C11 C17 1.500(2) . ?
C12 C15 1.386(2) . ?
C13 C15 1.384(2) . ?
C18 C20 1.388(3) . ?
C19 C20 1.386(3) . ?

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
C13 C3 N10 119.64(14) . . ?
C16 C3 N10 120.12(14) . . ?
C16 C3 C13 120.16(15) . . ?
C11 C4 N7 118.49(14) . . ?
C19 C4 N7 120.69(15) . . ?
C19 C4 C11 120.81(16) . . ?
C18 C6 C11 120.29(17) . . ?
C14 N7 C4 123.55(13) . . ?
C16 C9 C12 119.02(15) . . ?
C14 N10 C3 118.35(13) . . ?
C17 N10 C3 118.25(12) . . ?
C17 N10 C14 122.42(13) . . ?
C6 C11 C4 119.24(15) . . ?
C17 C11 C4 119.08(14) . . ?
C17 C11 C6 121.64(15) . . ?
C9 C12 Br1 118.81(12) . . ?
C15 C12 Br1 119.61(12) . . ?
C15 C12 C9 121.58(15) . . ?
C15 C13 C3 120.27(15) . . ?
N7 C14 O1 122.01(14) . . ?
N10 C14 O1 121.82(14) . . ?
N10 C14 N7 116.16(14) . . ?
C13 C15 C12 118.96(15) . . ?
C9 C16 C3 119.98(15) . . ?
N10 C17 O2 112.28(13) . . ?
C11 C17 O2 112.37(13) . . ?
C11 C17 N10 109.43(12) . . ?
C20 C18 C6 119.62(16) . . ?
C20 C19 C4 119.02(16) . . ?
C19 C20 C18 120.97(16) . . ?


_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_1(CF3)
_database_code_depnum_ccdc_archive 'CCDC 2059487'
loop_
_audit_author_name
_audit_author_address
'zou hanxun'
;Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2021-01-29 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;
_audit_creation_date             2019-12-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         '0.18(C15 H11 F3 N2 O2)'
_chemical_formula_sum            'C2.727 H2 F0.545 N0.364 O0.364'
_chemical_formula_weight         56.05
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H -0.00002 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
C 0.01476 0.00704 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
F 0.05995 0.04109 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
O 0.04121 0.02503 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
N 0.02530 0.01357 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   6.48980(10)
_cell_length_b                   9.4670(2)
_cell_length_c                   21.3064(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.6330(10)
_cell_angle_gamma                90
_cell_volume                     1304.77(4)
_cell_formula_units_Z            22
_cell_measurement_temperature    173.0(4)
_cell_measurement_reflns_used    7713
_cell_measurement_theta_min      3.6200
_cell_measurement_theta_max      60.3260
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.5691
_exptl_crystal_F_000             634.0313
_exptl_crystal_description       Prism
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8811
_diffrn_reflns_theta_full        60.3455
_diffrn_reflns_theta_max         60.35
_diffrn_reflns_theta_min         3.62
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.9688
_diffrn_measured_fraction_theta_max 0.9688
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     1.34139
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                2724
_reflns_number_total             2886
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.3393
_refine_diff_density_min         -0.4476
_refine_diff_density_rms         0.0554
_refine_ls_d_res_high            0.7718
_refine_ls_d_res_low             10.6184
_refine_ls_goodness_of_fit_ref   1.0443
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    22
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2886
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.0443
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0469P)²+1.0356P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1064
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 N6(H6), C8(H8), C9(H9), C10(H10), C13(H13), C17(H17), C19(H19), C20(H20),
 C22(H22)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
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_refinement_flags_posn
O1 O 0.17064(15) 0.89271(10) 0.07006(4) 0.0157(2) Uani 1.000000 .
F2 F -0.64450(14) 0.63550(12) 0.25123(5) 0.0348(3) Uani 1.000000 .
O3 O -0.35148(15) 1.14802(11) 0.03792(5) 0.0172(2) Uani 1.000000 .
H3 H -0.28837(16) 1.140(2) 0.00522(12) 0.0207(3) Uiso 1.000000 GR
F4 F -0.36025(15) 0.61213(11) 0.30899(4) 0.0299(2) Uani 1.000000 .
F5 F -0.42054(18) 0.48198(10) 0.22735(5) 0.0355(3) Uani 1.000000 .
N6 N 0.18997(18) 1.12854(13) 0.05124(5) 0.0160(2) Uani 1.000000 .
H6 H 0.29337(18) 1.11591(13) 0.02753(5) 0.0192(3) Uiso 1.000000 R
N7 N -0.07993(17) 1.03658(12) 0.10333(5) 0.0148(2) Uani 1.000000 .
C8 C -0.1399(2) 0.76530(16) 0.22601(7) 0.0195(3) Uani 1.000000 .
H8 H -0.0630(2) 0.72583(16) 0.26159(7) 0.0235(4) Uiso 1.000000 R
C9 C -0.4543(2) 0.77636(15) 0.15753(7) 0.0171(3) Uani 1.000000 .
H9 H -0.5919(2) 0.74546(15) 0.14676(7) 0.0206(3) Uiso 1.000000 R
C10 C -0.3647(2) 0.87652(15) 0.12082(7) 0.0169(3) Uani 1.000000 .
H10 H -0.4399(2) 0.91306(15) 0.08427(7) 0.0203(3) Uiso 1.000000 R
C11 C 0.0982(2) 1.01252(15) 0.07443(6) 0.0143(3) Uani 1.000000 .
C12 C -0.1655(2) 0.92326(15) 0.13752(6) 0.0146(3) Uani 1.000000 .
C13 C -0.0517(2) 0.86658(16) 0.18982(7) 0.0184(3) Uani 1.000000 .
H13 H 0.0860(2) 0.89739(16) 0.20057(7) 0.0221(3) Uiso 1.000000 R
C14 C -0.3418(2) 0.72160(15) 0.21001(6) 0.0160(3) Uani 1.000000 .
C15 C -0.0655(2) 1.28871(15) 0.08530(6) 0.0169(3) Uani 1.000000 .
C16 C -0.2054(2) 1.16399(15) 0.09124(6) 0.0155(3) Uani 1.000000 .
H16 H -0.2850(2) 1.18027(15) 0.12886(6) 0.0186(3) Uiso 1.000000 R
C17 C 0.2577(2) 1.38109(16) 0.05330(7) 0.0211(3) Uani 1.000000 .
H17 H 0.3890(2) 1.36604(16) 0.03773(7) 0.0253(4) Uiso 1.000000 R
C18 C 0.1280(2) 1.26711(15) 0.06322(6) 0.0161(3) Uani 1.000000 .
C19 C -0.1266(2) 1.42530(16) 0.09945(7) 0.0217(3) Uani 1.000000 .
H19 H -0.2569(2) 1.44048(16) 0.11568(7) 0.0260(4) Uiso 1.000000 R
C20 C 0.1926(3) 1.51641(17) 0.06643(7) 0.0247(3) Uani 1.000000 .
H20 H 0.2794(3) 1.59462(17) 0.05929(7) 0.0297(4) Uiso 1.000000 R
C21 C -0.4414(2) 0.61394(16) 0.24910(7) 0.0203(3) Uani 1.000000 .
C22 C 0.0013(3) 1.53920(17) 0.09000(7) 0.0252(3) Uani 1.000000 .
H22 H -0.0412(3) 1.63226(17) 0.09954(7) 0.0303(4) Uiso 1.000000 R


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
O1 C11 1.2342(17) . ?
F2 C21 1.3383(17) . ?
O3 C16 1.4276(16) . ?
F4 C21 1.3406(17) . ?
F5 C21 1.3430(19) . ?
N6 C11 1.3611(18) . ?
N6 C18 1.4016(18) . ?
N7 C11 1.3721(17) . ?
N7 C12 1.4337(17) . ?
N7 C16 1.4666(17) . ?
C8 C13 1.383(2) . ?
C8 C14 1.390(2) . ?
C9 C10 1.3863(19) . ?
C9 C14 1.3857(19) . ?
C10 C12 1.3855(19) . ?
C12 C13 1.3938(19) . ?
C14 C21 1.4955(19) . ?
C15 C16 1.5010(19) . ?
C15 C18 1.3916(19) . ?
C15 C19 1.393(2) . ?
C17 C18 1.395(2) . ?
C17 C20 1.384(2) . ?
C19 C22 1.385(2) . ?
C20 C22 1.393(2) . ?

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
C18 N6 C11 123.28(11) . . ?
C12 N7 C11 118.61(11) . . ?
C16 N7 C11 122.26(11) . . ?
C16 N7 C12 118.18(11) . . ?
C14 C8 C13 119.62(13) . . ?
C14 C9 C10 119.59(13) . . ?
C12 C10 C9 119.90(13) . . ?
N6 C11 O1 122.26(12) . . ?
N7 C11 O1 121.75(12) . . ?
N7 C11 N6 115.99(12) . . ?
C10 C12 N7 120.02(12) . . ?
C13 C12 N7 119.48(12) . . ?
C13 C12 C10 120.39(13) . . ?
C12 C13 C8 119.73(13) . . ?
C9 C14 C8 120.73(13) . . ?
C21 C14 C8 120.49(13) . . ?
C21 C14 C9 118.77(13) . . ?
C18 C15 C16 118.79(12) . . ?
C19 C15 C16 121.83(13) . . ?
C19 C15 C18 119.35(13) . . ?
N7 C16 O3 112.10(11) . . ?
C15 C16 O3 112.55(11) . . ?
C15 C16 N7 109.31(11) . . ?
C20 C17 C18 119.19(14) . . ?
C15 C18 N6 118.63(13) . . ?
C17 C18 N6 120.73(13) . . ?
C17 C18 C15 120.64(13) . . ?
C22 C19 C15 120.45(14) . . ?
C22 C20 C17 120.75(14) . . ?
F4 C21 F2 106.37(12) . . ?
F5 C21 F2 106.29(13) . . ?
F5 C21 F4 105.89(12) . . ?
C14 C21 F2 112.70(12) . . ?
C14 C21 F4 112.61(12) . . ?
C14 C21 F5 112.44(12) . . ?
C20 C22 C19 119.59(14) . . ?


_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_3(Br)
_database_code_depnum_ccdc_archive 'CCDC 2059488'
loop_
_audit_author_name
_audit_author_address
'zou hanxun'
;Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2021-01-29 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;
_audit_creation_date             2021-01-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_chemical_formula_moiety         'C14 H10 Br N2 O, C F3 O3 S'
_chemical_formula_sum            'C15 H10 Br F3 N2 O4 S'
_chemical_formula_weight         451.222
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   22.646(5)
_cell_length_b                   12.591(3)
_cell_length_c                   12.272(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.852(4)
_cell_angle_gamma                90
_cell_volume                     3480.9(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    173.15
_cell_measurement_reflns_used    4389
_cell_measurement_theta_min      2.4308
_cell_measurement_theta_max      27.4855
_exptl_absorpt_coefficient_mu    2.536
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.722
_exptl_crystal_F_000             1792.526
_exptl_crystal_description       Prism
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.9975
_diffrn_reflns_Laue_measured_fraction_max 0.9970
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13271
_diffrn_reflns_point_group_measured_fraction_full 0.9975
_diffrn_reflns_point_group_measured_fraction_max 0.9970
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         2.43
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.9970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              29
_reflns_limit_h_min              -29
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2909
_reflns_number_total             3959
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.6227
_refine_diff_density_min         -0.5390
_refine_diff_density_rms         0.0665
_refine_ls_d_res_high            0.7711
_refine_ls_d_res_low             8.3780
_refine_ls_goodness_of_fit_ref   0.9269
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3959
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0321
_refine_ls_restrained_S_all      0.9269
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0488P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0839
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), N2(H2), C7(H7), C8(H8), C13(H13), C15(H15), C17(H17), C18(H18),
 C20(H20), C21(H21)
;
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_refinement_flags_posn
Br1 Br 0.032926(10) 0.15036(2) 0.06849(2) 0.05915(11) Uani 1.000000 .
S2 S -0.18840(3) 0.49889(5) 0.40127(5) 0.04928(16) Uani 1.000000 .
C1 C -0.40202(11) 0.36685(19) 0.1919(2) 0.0541(6) Uani 1.000000 .
H1 H -0.43248(11) 0.40662(19) 0.1515(2) 0.0650(7) Uiso 1.000000 R
N2 N -0.27116(7) 0.19005(13) 0.36881(13) 0.0372(4) Uani 1.000000 .
H2 H -0.27892(7) 0.16178(13) 0.43136(13) 0.0447(5) Uiso 1.000000 R
N3 N -0.20730(7) 0.22234(13) 0.23445(13) 0.0379(4) Uani 1.000000 .
C4 C -0.04333(9) 0.17299(18) 0.11510(16) 0.0429(5) Uani 1.000000 .
O5 O -0.17825(7) 0.12130(13) 0.38703(13) 0.0541(4) Uani 1.000000 .
C6 C -0.31552(8) 0.24807(15) 0.31277(15) 0.0357(4) Uani 1.000000 .
C7 C -0.24746(9) 0.28366(16) 0.18008(17) 0.0410(5) Uani 1.000000 .
H7 H -0.23808(9) 0.31789(16) 0.11503(17) 0.0492(6) Uiso 1.000000 R
C8 C -0.11396(9) 0.29034(18) 0.18149(18) 0.0460(5) Uani 1.000000 .
H8 H -0.12594(9) 0.35958(18) 0.20073(18) 0.0552(6) Uiso 1.000000 R
C9 C -0.15047(8) 0.20433(17) 0.19213(16) 0.0395(5) Uani 1.000000 .
C10 C -0.30328(8) 0.29935(16) 0.21593(16) 0.0377(4) Uani 1.000000 .
C11 C -0.21651(9) 0.17203(16) 0.33718(16) 0.0387(5) Uani 1.000000 .
O12 O -0.19659(8) 0.39086(13) 0.43511(13) 0.0628(5) Uani 1.000000 .
C13 C -0.13498(10) 0.10320(18) 0.16340(18) 0.0474(5) Uani 1.000000 .
H13 H -0.16105(10) 0.04516(18) 0.17096(18) 0.0569(6) Uiso 1.000000 R
C15 C -0.08084(10) 0.08775(19) 0.12338(18) 0.0488(5) Uani 1.000000 .
H15 H -0.06950(10) 0.01889(19) 0.10169(18) 0.0585(6) Uiso 1.000000 R
C17 C -0.34774(10) 0.36066(18) 0.15579(19) 0.0495(6) Uani 1.000000 .
H17 H -0.33953(10) 0.39687(18) 0.09111(19) 0.0595(7) Uiso 1.000000 R
C18 C -0.05938(9) 0.27408(18) 0.14219(18) 0.0485(5) Uani 1.000000 .
H18 H -0.03340(9) 0.33216(18) 0.13410(18) 0.0582(6) Uiso 1.000000 R
C20 C -0.41361(10) 0.3155(2) 0.2876(2) 0.0547(6) Uani 1.000000 .
H20 H -0.45220(10) 0.3209(2) 0.3110(2) 0.0657(7) Uiso 1.000000 R
C21 C -0.37142(9) 0.25738(18) 0.34938(18) 0.0462(5) Uani 1.000000 .
H21 H -0.38011(9) 0.22432(18) 0.41548(18) 0.0555(6) Uiso 1.000000 R
F24 F -0.09218(9) 0.61424(16) 0.40879(17) 0.1110(7) Uani 1.000000 .
F25 F -0.07915(8) 0.45018(19) 0.3737(2) 0.1357(9) Uani 1.000000 .
O26 O -0.21284(9) 0.57852(16) 0.46626(16) 0.0830(6) Uani 1.000000 .
C27 C -0.10832(13) 0.5165(2) 0.4305(3) 0.0713(8) Uani 1.000000 .
O1 O -0.19888(9) 0.51285(15) 0.28584(14) 0.0763(6) Uani 1.000000 .
F2 F -0.09180(9) 0.49851(14) 0.53512(18) 0.1029(6) Uani 1.000000 .


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
Br1 C4 1.895(2) . ?
S2 O12 1.4397(17) . ?
S2 O26 1.4275(18) . ?
S2 C27 1.826(3) . ?
S2 O1 1.4230(18) . ?
C1 C17 1.351(3) . ?
C1 C20 1.389(3) . ?
N2 C6 1.369(2) . ?
N2 C11 1.353(3) . ?
N3 C7 1.321(2) . ?
N3 C9 1.454(2) . ?
N3 C11 1.445(2) . ?
C4 C15 1.379(3) . ?
C4 C18 1.374(3) . ?
O5 C11 1.194(2) . ?
C6 C10 1.405(3) . ?
C6 C21 1.391(3) . ?
C7 C10 1.394(3) . ?
C8 C9 1.377(3) . ?
C8 C18 1.387(3) . ?
C9 C13 1.376(3) . ?
C10 C17 1.415(3) . ?
C13 C15 1.380(3) . ?
C20 C21 1.370(3) . ?
F24 C27 1.318(3) . ?
F25 C27 1.309(3) . ?
C27 F2 1.320(4) . ?

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
O26 S2 O12 115.70(12) . . ?
C27 S2 O12 102.29(12) . . ?
C27 S2 O26 103.81(12) . . ?
O1 S2 O12 112.98(11) . . ?
O1 S2 O26 115.76(12) . . ?
O1 S2 C27 104.02(14) . . ?
C20 C1 C17 120.5(2) . . ?
C11 N2 C6 126.23(17) . . ?
C9 N3 C7 119.97(16) . . ?
C11 N3 C7 122.95(16) . . ?
C11 N3 C9 117.07(16) . . ?
C15 C4 Br1 119.50(17) . . ?
C18 C4 Br1 118.94(16) . . ?
C18 C4 C15 121.5(2) . . ?
C10 C6 N2 118.17(17) . . ?
C21 C6 N2 121.88(18) . . ?
C21 C6 C10 119.94(18) . . ?
C10 C7 N3 121.53(18) . . ?
C18 C8 C9 118.8(2) . . ?
C8 C9 N3 118.24(19) . . ?
C13 C9 N3 119.59(19) . . ?
C13 C9 C8 122.17(19) . . ?
C7 C10 C6 117.73(17) . . ?
C17 C10 C6 120.05(18) . . ?
C17 C10 C7 122.17(19) . . ?
N3 C11 N2 113.21(17) . . ?
O5 C11 N2 125.44(19) . . ?
O5 C11 N3 121.34(19) . . ?
C15 C13 C9 118.7(2) . . ?
C13 C15 C4 119.5(2) . . ?
C10 C17 C1 118.9(2) . . ?
C8 C18 C4 119.2(2) . . ?
C21 C20 C1 122.4(2) . . ?
C20 C21 C6 118.2(2) . . ?
F24 C27 S2 111.3(2) . . ?
F25 C27 S2 111.3(2) . . ?
F25 C27 F24 108.8(3) . . ?
F2 C27 S2 110.3(2) . . ?
F2 C27 F24 107.5(2) . . ?
F2 C27 F25 107.4(3) . . ?

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
Br1 C4 C15 C13 176.23(17) . . . . ?
Br1 C4 C18 C8 -176.85(16) . . . . ?
C1 C17 C10 C6 -1.4(3) . . . . ?
C1 C17 C10 C7 175.8(2) . . . . ?
C1 C20 C21 C6 -1.5(3) . . . . ?
N2 C6 C10 C7 3.0(2) . . . . ?
N2 C6 C10 C17 -179.63(18) . . . . ?
N2 C6 C21 C20 -179.0(2) . . . . ?
N2 C11 N3 C7 3.0(2) . . . . ?
N2 C11 N3 C9 -177.98(16) . . . . ?
N3 C7 C10 C6 0.4(2) . . . . ?
N3 C7 C10 C17 -176.89(19) . . . . ?
N3 C9 C8 C18 179.40(19) . . . . ?
N3 C9 C13 C15 180.00(19) . . . . ?
C4 C15 C13 C9 1.2(3) . . . . ?
C4 C18 C8 C9 -0.0(2) . . . . ?
C8 C9 C13 C15 0.5(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_4(F)
_audit_block_doi                 10.5517/ccdc.csd.cc27vg7t
_database_code_depnum_ccdc_archive 'CCDC 2081006'
loop_
_audit_author_name
_audit_author_address
'Hanxun Zou'
;Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2021-04-29 deposited with the CCDC.	2021-05-18 downloaded from the CCDC.
;
_audit_creation_date             2021-04-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C17 H17 F N2 O S'
_chemical_formula_sum            'C17 H17 F N2 O S'
_chemical_formula_weight         316.40
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01470 0.00700 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
F 0.05990 0.04100 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
H -0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
O 0.04120 0.02500 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
N 0.02530 0.01350 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom
S 0.29220 0.42420 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)' custom

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.7848(3)
_cell_length_b                   8.4793(3)
_cell_length_c                   19.1995(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.115(3)
_cell_angle_gamma                90
_cell_volume                     1586.61(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    156(8)
_cell_measurement_reflns_used    4680
_cell_measurement_theta_min      4.0180
_cell_measurement_theta_max      50.5250
_exptl_crystal_description       Prism
_exptl_absorpt_coefficient_mu    1.249
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.3245
_exptl_crystal_F_000             666.6733
_diffrn_ambient_temperature      156(8)
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8261
_diffrn_reflns_theta_full        50.5748
_diffrn_reflns_theta_max         50.57
_diffrn_reflns_theta_min         4.02
_diffrn_measured_fraction_theta_full 0.9882
_diffrn_measured_fraction_theta_max 0.9882
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     1.3405
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -11
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              -8
_reflns_number_gt                2111
_reflns_number_total             2506
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.4919
_refine_diff_density_min         -0.5835
_refine_diff_density_rms         0.0531
_refine_ls_d_res_high            0.8677
_refine_ls_d_res_low             9.5615
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0535
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2506
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.0535
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0814P)²+1.2528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1569
_refine_ls_wR_factor_ref         0.1647
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C0aa(H0aa,H0ab), C19(H19a,H19b)
2.c Aromatic/amide H refined with riding coordinates:
 N10(H10), C16(H16), C15(H15), C5(H5), C2(H2), C4(H4), C12(H12), C3(H3),
 C13(H13)
2.d Idealised Me refined as rotating group:
 C1aa(H1aa,H1ab,H1ac)
;
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_refinement_flags_posn
S18 S 0.37059(10) 0.47513(10) 0.58336(5) 0.0733(4) Uani 1.000000 .
O20 O 0.01782(19) 0.1837(2) 0.45491(10) 0.0529(5) Uani 1.000000 .
F17 F 0.1162(3) 0.7707(3) 0.28289(11) 0.0946(8) Uani 1.000000 .
N8 N 0.2250(2) 0.3013(3) 0.47924(12) 0.0452(6) Uani 1.000000 .
N10 N 0.1723(2) 0.0667(3) 0.53276(12) 0.0496(6) Uani 1.000000 .
H10 H 0.1107(2) 0.0019(3) 0.54450(12) 0.0595(7) Uiso 1.000000 R
C9 C 0.1328(3) 0.1837(3) 0.48754(14) 0.0440(6) Uani 1.000000 .
C11 C 0.1900(3) 0.4221(3) 0.42816(14) 0.0446(6) Uani 1.000000 .
C6 C 0.4025(3) 0.1620(3) 0.55360(14) 0.0461(7) Uani 1.000000 .
C1 C 0.3074(3) 0.0447(3) 0.56160(14) 0.0449(7) Uani 1.000000 .
C16 C 0.1402(3) 0.5659(3) 0.44789(16) 0.0512(7) Uani 1.000000 .
H16 H 0.1239(3) 0.5835(3) 0.49423(16) 0.0614(9) Uiso 1.000000 R
C15 C 0.1144(3) 0.6841(4) 0.39859(17) 0.0581(8) Uani 1.000000 .
H15 H 0.0812(3) 0.7818(4) 0.41119(17) 0.0697(10) Uiso 1.000000 R
C7 C 0.3588(3) 0.3143(3) 0.51997(15) 0.0488(7) Uani 1.000000 .
H7 H 0.4256(3) 0.3379(3) 0.48634(15) 0.0586(8) Uiso 1.000000 R
C14 C 0.1390(3) 0.6534(4) 0.33142(17) 0.0622(9) Uani 1.000000 .
C5 C 0.5385(3) 0.1371(4) 0.57971(15) 0.0548(8) Uani 1.000000 .
H5 H 0.6040(3) 0.2143(4) 0.57373(15) 0.0657(9) Uiso 1.000000 R
C2 C 0.3452(3) -0.0931(4) 0.59681(15) 0.0548(8) Uani 1.000000 .
H2 H 0.2803(3) -0.1711(4) 0.60255(15) 0.0658(9) Uiso 1.000000 R
C4 C 0.5765(3) 0.0007(4) 0.61391(17) 0.0621(8) Uani 1.000000 .
H4 H 0.6675(3) -0.0150(4) 0.63088(17) 0.0745(10) Uiso 1.000000 R
C12 C 0.2124(4) 0.3962(4) 0.35989(17) 0.0677(9) Uani 1.000000 .
H12 H 0.2450(4) 0.2987(4) 0.34658(17) 0.0812(11) Uiso 1.000000 R
C3 C 0.4792(3) -0.1142(4) 0.62328(17) 0.0616(8) Uani 1.000000 .
H3 H 0.5047(3) -0.2060(4) 0.64757(17) 0.0739(10) Uiso 1.000000 R
C13 C 0.1871(4) 0.5134(5) 0.31041(18) 0.0813(11) Uani 1.000000 .
H13 H 0.2028(4) 0.4965(5) 0.26393(18) 0.0976(14) Uiso 1.000000 R
C19 C 0.2561(5) 0.4125(7) 0.6463(3) 0.1136(18) Uani 1.000000 .
C0aa C 0.3043(11) 0.4226(19) 0.7171(4) 0.275(7) Uani 1.000000 .
C1aa C 0.4201(9) 0.3898(13) 0.7529(4) 0.211(4) Uani 1.000000 .
H0aa H 0.2880(11) 0.5319(19) 0.7288(4) 0.330(9) Uiso 1.000000 R
H0ab H 0.2375(11) 0.3625(19) 0.7405(4) 0.330(9) Uiso 1.000000 R
H1aa H 0.4947(10) 0.416(10) 0.7258(19) 0.316(7) Uiso 1.000000 GR
H1ab H 0.428(4) 0.450(8) 0.795(2) 0.316(7) Uiso 1.000000 GR
H1ac H 0.423(4) 0.279(2) 0.764(4) 0.316(7) Uiso 1.000000 GR
H19a H 0.1730(5) 0.4749(7) 0.6391(3) 0.136(2) Uiso 1.000000 R
H19b H 0.2310(5) 0.3036(7) 0.6362(3) 0.136(2) Uiso 1.000000 R


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
S18 C7 1.825(3) . ?
S18 C19 1.799(5) . ?
O20 C9 1.238(3) . ?
F17 C14 1.367(3) . ?
N8 C9 1.363(3) . ?
N8 C11 1.438(3) . ?
N8 C7 1.468(3) . ?
N10 H10 0.8600 . ?
N10 C9 1.352(3) . ?
N10 C1 1.400(3) . ?
C11 C16 1.378(4) . ?
C11 C12 1.366(4) . ?
C6 C1 1.380(4) . ?
C6 C7 1.489(4) . ?
C6 C5 1.396(4) . ?
C1 C2 1.384(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.386(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.358(5) . ?
C7 H7 0.9800 . ?
C14 C13 1.352(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.365(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.385(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.382(5) . ?
C3 H3 0.9300 . ?
C13 H13 0.9300 . ?
C19 C0aa 1.402(9) . ?
C19 H19a 0.9700 . ?
C19 H19b 0.9700 . ?
C0aa C1aa 1.302(11) . ?
C0aa H0aa 0.9700 . ?
C0aa H0ab 0.9700 . ?
C1aa H1aa 0.9600 . ?
C1aa H1ab 0.9600 . ?
C1aa H1ac 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
C19 S18 C7 102.76(18) . . ?
C11 N8 C9 118.7(2) . . ?
C7 N8 C9 124.1(2) . . ?
C7 N8 C11 117.2(2) . . ?
C9 N10 H10 118.05(14) . . ?
C1 N10 H10 118.05(14) . . ?
C1 N10 C9 123.9(2) . . ?
N8 C9 O20 121.5(2) . . ?
N10 C9 O20 121.3(2) . . ?
N10 C9 N8 117.2(2) . . ?
C16 C11 N8 120.7(2) . . ?
C12 C11 N8 119.4(3) . . ?
C12 C11 C16 119.8(3) . . ?
C7 C6 C1 120.2(2) . . ?
C5 C6 C1 118.8(3) . . ?
C5 C6 C7 121.0(2) . . ?
C6 C1 N10 118.8(2) . . ?
C2 C1 N10 120.5(2) . . ?
C2 C1 C6 120.7(3) . . ?
H16 C16 C11 120.03(16) . . ?
C15 C16 C11 119.9(3) . . ?
C15 C16 H16 120.03(18) . . ?
H15 C15 C16 120.88(18) . . ?
C14 C15 C16 118.2(3) . . ?
C14 C15 H15 120.88(19) . . ?
N8 C7 S18 114.3(2) . . ?
C6 C7 S18 111.11(19) . . ?
C6 C7 N8 111.9(2) . . ?
H7 C7 S18 106.28(9) . . ?
H7 C7 N8 106.28(14) . . ?
H7 C7 C6 106.28(16) . . ?
C15 C14 F17 118.4(3) . . ?
C13 C14 F17 118.4(3) . . ?
C13 C14 C15 123.2(3) . . ?
H5 C5 C6 119.63(17) . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.63(18) . . ?
H2 C2 C1 120.18(17) . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2 120.18(19) . . ?
H4 C4 C5 120.07(18) . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.07(18) . . ?
H12 C12 C11 119.68(18) . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7(2) . . ?
C4 C3 C2 120.3(3) . . ?
H3 C3 C2 119.85(19) . . ?
H3 C3 C4 119.85(18) . . ?
C12 C13 C14 118.2(3) . . ?
H13 C13 C14 120.9(2) . . ?
H13 C13 C12 120.9(2) . . ?
C0aa C19 S18 117.2(5) . . ?
H19a C19 S18 107.99(19) . . ?
H19a C19 C0aa 108.0(6) . . ?
H19b C19 S18 107.99(16) . . ?
H19b C19 C0aa 108.0(7) . . ?
H19b C19 H19a 107.2 . . ?
C1aa C0aa C19 134.5(10) . . ?
H0aa C0aa C19 103.6(7) . . ?
H0aa C0aa C1aa 103.6(9) . . ?
H0ab C0aa C19 103.6(5) . . ?
H0ab C0aa C1aa 103.6(6) . . ?
H0ab C0aa H0aa 105.295577008(15) . . ?
H1aa C1aa C0aa 109.5 . . ?
H1ab C1aa C0aa 109.5 . . ?
H1ab C1aa H1aa 109.5 . . ?
H1ac C1aa C0aa 109.5 . . ?
H1ac C1aa H1aa 109.5 . . ?
H1ac C1aa H1ab 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'

