# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2402930'
loop_
_audit_author_name
_audit_author_address
'Xiyan Duan'
;Henan University of Science and Technology
China
;
_audit_update_record             
;
2024-11-15 deposited with the CCDC.	2025-03-27 downloaded from the CCDC.
;
_audit_creation_date             2024-05-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 Br2 F3 N O2'
_chemical_formula_sum            'C14 H12 Br2 F3 N O2'
_chemical_formula_weight         443.07
_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'
Br Br -0.2901 2.4595 '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                   7.8205(4)
_cell_length_b                   9.2042(4)
_cell_length_c                   11.7867(5)
_cell_angle_alpha                69.3080(10)
_cell_angle_beta                 77.6970(10)
_cell_angle_gamma                86.335(2)
_cell_volume                     775.41(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5488
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   0.451
_shelx_estimated_absorpt_T_min   0.391
_exptl_absorpt_coefficient_mu    5.264
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4191
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1365 before and 0.0504 after correction.
The Ratio of minimum to maximum transmission is 0.5620.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14548
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.329
_diffrn_reflns_theta_min         2.666
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2496
_reflns_number_total             3807
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.929
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3807
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0867
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.017
_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)+(0.0445P)²+0.8279P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.1080
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_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
Br1 Br 0.45148(5) 0.39244(5) 0.36477(4) 0.04757(15) Uani 1 1 d . . . . .
Br2 Br 0.79097(6) 0.43700(6) -0.06238(4) 0.05536(17) Uani 1 1 d . . . . .
C1 C 0.7549(6) -0.0659(6) 0.9242(4) 0.0539(12) Uani 1 1 d . . . . .
C2 C 0.7452(5) -0.0031(4) 0.7914(4) 0.0364(9) Uani 1 1 d . . . . .
C3 C 0.6748(5) 0.1411(5) 0.7416(4) 0.0427(10) Uani 1 1 d . . . . .
H3 H 0.6352 0.2005 0.7912 0.051 Uiso 1 1 calc R U . . .
C4 C 0.6631(6) 0.1974(5) 0.6185(4) 0.0416(10) Uani 1 1 d . . . . .
H4 H 0.6159 0.2949 0.5854 0.050 Uiso 1 1 calc R U . . .
C5 C 0.7219(5) 0.1087(4) 0.5429(3) 0.0335(8) Uani 1 1 d . . . . .
C6 C 0.7900(5) -0.0372(4) 0.5952(4) 0.0366(9) Uani 1 1 d . . . . .
H6 H 0.8285 -0.0981 0.5465 0.044 Uiso 1 1 calc R U . . .
C7 C 0.8010(5) -0.0926(5) 0.7181(4) 0.0402(9) Uani 1 1 d . . . . .
H7 H 0.8462 -0.1907 0.7521 0.048 Uiso 1 1 calc R U . . .
C8 C 0.7114(5) 0.1632(4) 0.4110(3) 0.0331(8) Uani 1 1 d . . . . .
C9 C 0.6996(5) 0.3343(4) 0.3313(3) 0.0327(8) Uani 1 1 d . . . . .
C10 C 0.7537(5) 0.3227(4) 0.2004(3) 0.0374(9) Uani 1 1 d . . . . .
H10 H 0.8818 0.3287 0.1782 0.045 Uiso 1 1 calc R U . . .
C11 C 0.7017(6) 0.1561(5) 0.2253(4) 0.0415(10) Uani 1 1 d . . . . .
H11A H 0.5834 0.1516 0.2134 0.050 Uiso 1 1 calc R U . . .
H11B H 0.7805 0.1136 0.1697 0.050 Uiso 1 1 calc R U . . .
C12 C 0.6877(7) 0.4481(6) 0.0999(4) 0.0548(12) Uani 1 1 d . . . . .
H12A H 0.7153 0.5484 0.1018 0.066 Uiso 1 1 calc R U . . .
H12B H 0.5614 0.4389 0.1141 0.066 Uiso 1 1 calc R U . . .
C13 C 0.8223(6) 0.4430(4) 0.3480(3) 0.0376(9) Uani 1 1 d . . . . .
C14 C 0.8803(8) 0.6969(6) 0.3319(6) 0.0837(19) Uani 1 1 d . . . . .
H14A H 0.9745 0.7203 0.2608 0.126 Uiso 1 1 calc R U . . .
H14B H 0.9266 0.6541 0.4059 0.126 Uiso 1 1 calc R U . . .
H14C H 0.8181 0.7903 0.3319 0.126 Uiso 1 1 calc R U . . .
F1 F 0.7425(7) 0.0351(4) 0.9777(3) 0.1203(16) Uani 1 1 d . . . . .
F2 F 0.8907(5) -0.1547(5) 0.9469(3) 0.1044(13) Uani 1 1 d . . . . .
F3 F 0.6223(5) -0.1669(4) 0.9924(3) 0.1000(12) Uani 1 1 d . . . . .
N1 N 0.7126(4) 0.0696(4) 0.3529(3) 0.0404(8) Uani 1 1 d . . . . .
O1 O 0.9629(4) 0.4016(4) 0.3684(3) 0.0578(8) Uani 1 1 d . . . . .
O2 O 0.7620(4) 0.5853(3) 0.3273(3) 0.0570(8) 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
Br1 C9 1.974(4) . ?
Br2 C12 1.947(4) . ?
C1 C2 1.482(6) . ?
C1 F1 1.283(5) . ?
C1 F2 1.313(5) . ?
C1 F3 1.351(6) . ?
C2 C3 1.379(6) . ?
C2 C7 1.382(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.401(5) . ?
C5 C6 1.390(5) . ?
C5 C8 1.474(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.376(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.531(5) . ?
C8 N1 1.275(5) . ?
C9 C10 1.550(5) . ?
C9 C13 1.518(6) . ?
C10 H10 0.9800 . ?
C10 C11 1.521(5) . ?
C10 C12 1.490(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 N1 1.450(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O1 1.186(5) . ?
C13 O2 1.320(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 O2 1.447(6) . ?

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
F1 C1 C2 115.4(4) . . ?
F1 C1 F2 110.2(4) . . ?
F1 C1 F3 103.8(4) . . ?
F2 C1 C2 113.7(4) . . ?
F2 C1 F3 100.8(4) . . ?
F3 C1 C2 111.7(4) . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 C7 119.8(4) . . ?
C7 C2 C1 119.6(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(4) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C8 122.5(3) . . ?
C6 C5 C4 118.5(3) . . ?
C6 C5 C8 118.9(3) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6 119.7 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.3(4) . . ?
C6 C7 H7 119.8 . . ?
C5 C8 C9 124.0(3) . . ?
N1 C8 C5 122.1(3) . . ?
N1 C8 C9 113.9(3) . . ?
C8 C9 Br1 106.9(2) . . ?
C8 C9 C10 100.0(3) . . ?
C10 C9 Br1 110.9(3) . . ?
C13 C9 Br1 112.8(2) . . ?
C13 C9 C8 114.8(3) . . ?
C13 C9 C10 110.8(3) . . ?
C9 C10 H10 107.0 . . ?
C11 C10 C9 101.8(3) . . ?
C11 C10 H10 107.0 . . ?
C12 C10 C9 115.6(3) . . ?
C12 C10 H10 107.0 . . ?
C12 C10 C11 117.8(4) . . ?
C10 C11 H11A 110.5 . . ?
C10 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
N1 C11 C10 106.3(3) . . ?
N1 C11 H11A 110.5 . . ?
N1 C11 H11B 110.5 . . ?
Br2 C12 H12A 109.3 . . ?
Br2 C12 H12B 109.3 . . ?
C10 C12 Br2 111.5(3) . . ?
C10 C12 H12A 109.3 . . ?
C10 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
O1 C13 C9 120.8(4) . . ?
O1 C13 O2 125.5(4) . . ?
O2 C13 C9 113.4(4) . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
C8 N1 C11 109.7(3) . . ?
C13 O2 C14 115.6(4) . . ?

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 C9 C10 C11 -86.5(3) . . . . ?
Br1 C9 C10 C12 42.4(4) . . . . ?
Br1 C9 C13 O1 157.0(3) . . . . ?
Br1 C9 C13 O2 -28.2(4) . . . . ?
C1 C2 C3 C4 -178.7(4) . . . . ?
C1 C2 C7 C6 178.8(4) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C3 C2 C7 C6 1.3(6) . . . . ?
C3 C4 C5 C6 0.7(6) . . . . ?
C3 C4 C5 C8 179.7(4) . . . . ?
C4 C5 C6 C7 -0.6(6) . . . . ?
C4 C5 C8 C9 22.5(6) . . . . ?
C4 C5 C8 N1 -157.9(4) . . . . ?
C5 C6 C7 C2 -0.4(6) . . . . ?
C5 C8 C9 Br1 -82.2(4) . . . . ?
C5 C8 C9 C10 162.2(3) . . . . ?
C5 C8 C9 C13 43.7(5) . . . . ?
C5 C8 N1 C11 -179.8(3) . . . . ?
C6 C5 C8 C9 -158.5(4) . . . . ?
C6 C5 C8 N1 21.1(6) . . . . ?
C7 C2 C3 C4 -1.2(6) . . . . ?
C8 C5 C6 C7 -179.6(3) . . . . ?
C8 C9 C10 C11 25.9(4) . . . . ?
C8 C9 C10 C12 154.9(4) . . . . ?
C8 C9 C13 O1 34.3(5) . . . . ?
C8 C9 C13 O2 -150.9(3) . . . . ?
C9 C8 N1 C11 -0.1(5) . . . . ?
C9 C10 C11 N1 -27.9(4) . . . . ?
C9 C10 C12 Br2 172.0(3) . . . . ?
C9 C13 O2 C14 -175.0(4) . . . . ?
C10 C9 C13 O1 -77.9(5) . . . . ?
C10 C9 C13 O2 96.8(4) . . . . ?
C10 C11 N1 C8 18.5(4) . . . . ?
C11 C10 C12 Br2 -67.4(4) . . . . ?
C12 C10 C11 N1 -155.5(3) . . . . ?
C13 C9 C10 C11 147.4(3) . . . . ?
C13 C9 C10 C12 -83.7(4) . . . . ?
F1 C1 C2 C3 -19.0(7) . . . . ?
F1 C1 C2 C7 163.5(4) . . . . ?
F2 C1 C2 C3 -147.7(4) . . . . ?
F2 C1 C2 C7 34.8(6) . . . . ?
F3 C1 C2 C3 99.1(5) . . . . ?
F3 C1 C2 C7 -78.4(5) . . . . ?
N1 C8 C9 Br1 98.2(3) . . . . ?
N1 C8 C9 C10 -17.4(4) . . . . ?
N1 C8 C9 C13 -135.9(4) . . . . ?
O1 C13 O2 C14 -0.6(6) . . . . ?

_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
_database_code_depnum_ccdc_archive 'CCDC 2429981'
loop_
_audit_author_name
_audit_author_address
'Xiyan Duan'
;Henan University of Science and Technology
China
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-03-27 downloaded from the CCDC.
;
_audit_creation_date             2025-03-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H11 N O2 S'
_chemical_formula_sum            'C11 H11 N O2 S'
_chemical_formula_weight         221.27
_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'
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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.601(3)
_cell_length_b                   6.611(3)
_cell_length_c                   24.701(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.223(14)
_cell_angle_gamma                90
_cell_volume                     1069.4(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4018
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.95
_cell_measurement_theta_min      3.12
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.941
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6707
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0745 before and 0.0646 after correction.
The Ratio of minimum to maximum transmission is 0.9000.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11335
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.030
_diffrn_reflns_theta_max         25.030
_diffrn_reflns_theta_min         3.117
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1381
_reflns_number_total             1858
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1858
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0536
_refine_ls_restrained_S_all      1.064
_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)+(0.0401P)²+1.4838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1306
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
C1 C 0.7507(6) 0.8222(7) 0.50810(14) 0.0669(12) Uani 1 1 d . . . . .
H1A H 0.7385 0.9669 0.5080 0.100 Uiso 1 1 calc R U . . .
H1B H 0.8893 0.7850 0.5206 0.100 Uiso 1 1 calc R U . . .
H1C H 0.6618 0.7655 0.5320 0.100 Uiso 1 1 calc R U . . .
C2 C 0.6960(5) 0.5457(6) 0.44741(13) 0.0422(8) Uani 1 1 d . . . . .
C3 C 0.6481(5) 0.4837(5) 0.38970(12) 0.0393(8) Uani 1 1 d . . . . .
C4 C 0.6320(6) 0.2613(6) 0.37602(16) 0.0580(11) Uani 1 1 d . . . . .
H4A H 0.6496 0.1659 0.4061 0.070 Uiso 1 1 calc R U . . .
H4B H 0.5327 0.2208 0.3456 0.070 Uiso 1 1 calc R U . . .
C5 C 0.8144(6) 0.3730(5) 0.36342(14) 0.0493(9) Uani 1 1 d . . . . .
H5 H 0.9464 0.3468 0.3852 0.059 Uiso 1 1 calc R U . . .
C6 C 0.8105(6) 0.4655(6) 0.30717(13) 0.0513(10) Uani 1 1 d . . . . .
H6A H 0.9357 0.5397 0.3046 0.062 Uiso 1 1 calc R U . . .
H6B H 0.7971 0.3607 0.2795 0.062 Uiso 1 1 calc R U . . .
C7 C 0.5535(5) 0.6164(5) 0.34412(11) 0.0348(7) Uani 1 1 d . . . . .
C8 C 0.3706(5) 0.7366(5) 0.34667(11) 0.0352(8) Uani 1 1 d . . . . .
C9 C 0.2511(5) 0.7549(5) 0.38771(13) 0.0423(8) Uani 1 1 d . . . . .
H9 H 0.2784 0.6895 0.4212 0.051 Uiso 1 1 calc R U . . .
C10 C 0.0830(5) 0.8828(6) 0.37410(14) 0.0507(10) Uani 1 1 d . . . . .
H10 H -0.0136 0.9109 0.3974 0.061 Uiso 1 1 calc R U . . .
C11 C 0.0771(6) 0.9603(6) 0.32349(14) 0.0519(10) Uani 1 1 d . . . . .
H11 H -0.0234 1.0489 0.3081 0.062 Uiso 1 1 calc R U . . .
N1 N 0.6341(4) 0.6023(4) 0.29946(10) 0.0434(7) Uani 1 1 d . . . . .
O1 O 0.7377(4) 0.4294(4) 0.48465(10) 0.0659(8) Uani 1 1 d . . . . .
O2 O 0.6942(4) 0.7456(4) 0.45321(8) 0.0489(7) Uani 1 1 d . . . . .
S1 S 0.27430(14) 0.87810(14) 0.29079(3) 0.0465(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 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 O2 1.452(4) . ?
C2 C3 1.479(4) . ?
C2 O1 1.204(4) . ?
C2 O2 1.330(4) . ?
C3 C4 1.509(5) . ?
C3 C5 1.530(5) . ?
C3 C7 1.500(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.479(5) . ?
C5 H5 0.9800 . ?
C5 C6 1.515(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 N1 1.468(4) . ?
C7 C8 1.453(4) . ?
C7 N1 1.287(4) . ?
C8 C9 1.366(4) . ?
C8 S1 1.722(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.402(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.347(5) . ?
C11 H11 0.9300 . ?
C11 S1 1.705(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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
O1 C2 C3 124.1(3) . . ?
O1 C2 O2 123.8(3) . . ?
O2 C2 C3 112.1(3) . . ?
C2 C3 C4 119.1(3) . . ?
C2 C3 C5 117.6(3) . . ?
C2 C3 C7 125.4(3) . . ?
C4 C3 C5 58.2(2) . . ?
C7 C3 C4 113.0(3) . . ?
C7 C3 C5 102.4(3) . . ?
C3 C4 H4A 117.6 . . ?
C3 C4 H4B 117.6 . . ?
H4A C4 H4B 114.7 . . ?
C5 C4 C3 61.6(2) . . ?
C5 C4 H4A 117.6 . . ?
C5 C4 H4B 117.6 . . ?
C3 C5 H5 119.1 . . ?
C4 C5 C3 60.2(2) . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 118.3(3) . . ?
C6 C5 C3 105.4(3) . . ?
C6 C5 H5 119.1 . . ?
C5 C6 H6A 110.4 . . ?
C5 C6 H6B 110.4 . . ?
H6A C6 H6B 108.6 . . ?
N1 C6 C5 106.8(3) . . ?
N1 C6 H6A 110.4 . . ?
N1 C6 H6B 110.4 . . ?
C8 C7 C3 123.9(3) . . ?
N1 C7 C3 115.0(3) . . ?
N1 C7 C8 120.8(3) . . ?
C7 C8 S1 119.2(2) . . ?
C9 C8 C7 129.9(3) . . ?
C9 C8 S1 110.9(2) . . ?
C8 C9 H9 123.6 . . ?
C8 C9 C10 112.9(3) . . ?
C10 C9 H9 123.6 . . ?
C9 C10 H10 123.8 . . ?
C11 C10 C9 112.4(3) . . ?
C11 C10 H10 123.8 . . ?
C10 C11 H11 123.7 . . ?
C10 C11 S1 112.6(3) . . ?
S1 C11 H11 123.7 . . ?
C7 N1 C6 109.9(3) . . ?
C2 O2 C1 116.3(3) . . ?
C11 S1 C8 91.15(17) . . ?

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
C2 C3 C4 C5 -106.2(3) . . . . ?
C2 C3 C5 C4 108.7(4) . . . . ?
C2 C3 C5 C6 -137.1(3) . . . . ?
C2 C3 C7 C8 -49.6(5) . . . . ?
C2 C3 C7 N1 137.0(3) . . . . ?
C3 C2 O2 C1 -176.7(3) . . . . ?
C3 C4 C5 C6 -92.2(3) . . . . ?
C3 C5 C6 N1 -6.8(4) . . . . ?
C3 C7 C8 C9 -0.2(5) . . . . ?
C3 C7 C8 S1 -178.5(2) . . . . ?
C3 C7 N1 C6 -3.8(4) . . . . ?
C4 C3 C5 C6 114.1(3) . . . . ?
C4 C3 C7 C8 112.2(4) . . . . ?
C4 C3 C7 N1 -61.2(4) . . . . ?
C4 C5 C6 N1 57.3(4) . . . . ?
C5 C3 C7 C8 172.7(3) . . . . ?
C5 C3 C7 N1 -0.7(4) . . . . ?
C5 C6 N1 C7 6.7(4) . . . . ?
C7 C3 C4 C5 90.6(3) . . . . ?
C7 C3 C5 C4 -109.6(3) . . . . ?
C7 C3 C5 C6 4.6(4) . . . . ?
C7 C8 C9 C10 -178.4(3) . . . . ?
C7 C8 S1 C11 178.9(3) . . . . ?
C8 C7 N1 C6 -177.4(3) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C9 C8 S1 C11 0.4(3) . . . . ?
C9 C10 C11 S1 0.6(4) . . . . ?
C10 C11 S1 C8 -0.5(3) . . . . ?
N1 C7 C8 C9 172.8(3) . . . . ?
N1 C7 C8 S1 -5.5(4) . . . . ?
O1 C2 C3 C4 5.5(5) . . . . ?
O1 C2 C3 C5 -61.6(5) . . . . ?
O1 C2 C3 C7 166.3(3) . . . . ?
O1 C2 O2 C1 1.2(5) . . . . ?
O2 C2 C3 C4 -176.6(3) . . . . ?
O2 C2 C3 C5 116.2(3) . . . . ?
O2 C2 C3 C7 -15.8(5) . . . . ?
S1 C8 C9 C10 -0.1(4) . . . . ?

_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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2429993'
loop_
_audit_author_name
_audit_author_address
'Xiyan Duan'
;Henan University of Science and Technology
China
;
_audit_update_record             
;
2025-03-10 deposited with the CCDC.	2025-03-27 downloaded from the CCDC.
;
_audit_creation_date             2024-11-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 Cl2 N O3'
_chemical_formula_sum            'C14 H15 Cl2 N O3'
_chemical_formula_weight         316.17
_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'
Cl Cl 0.1484 0.1585 '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                   7.1404(6)
_cell_length_b                   9.9152(10)
_cell_length_c                   11.5518(10)
_cell_angle_alpha                102.274(3)
_cell_angle_beta                 95.146(2)
_cell_angle_gamma                111.046(2)
_cell_volume                     733.38(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2603
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.74
_cell_measurement_theta_min      3.06
_shelx_estimated_absorpt_T_max   0.924
_shelx_estimated_absorpt_T_min   0.908
_exptl_absorpt_coefficient_mu    0.448
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6772
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0687 before and 0.0586 after correction.
The Ratio of minimum to maximum transmission is 0.9087.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9849
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.048
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_min         2.523
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1541
_reflns_number_total             2563
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2563
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.013
_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)+(0.0233P)²+0.6799P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.1063
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C)
;
_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
C1 C -0.4866(5) -0.0028(4) 0.1788(3) 0.0690(11) Uani 1 1 d . . . . .
H1A H -0.5017 0.0598 0.1287 0.103 Uiso 1 1 calc R U . . .
H1B H -0.6070 -0.0373 0.2132 0.103 Uiso 1 1 calc R U . . .
H1C H -0.4675 -0.0872 0.1313 0.103 Uiso 1 1 calc R U . . .
C2 C -0.1313(5) 0.1482(4) 0.2411(3) 0.0478(9) Uani 1 1 d . . . . .
C3 C -0.0944(6) 0.1269(4) 0.1240(3) 0.0522(9) Uani 1 1 d . . . . .
H3 H -0.1987 0.0621 0.0604 0.063 Uiso 1 1 calc R U . . .
C4 C 0.0970(5) 0.2018(4) 0.1024(3) 0.0500(9) Uani 1 1 d . . . . .
H4 H 0.1203 0.1859 0.0236 0.060 Uiso 1 1 calc R U . . .
C5 C 0.2559(5) 0.3002(3) 0.1945(3) 0.0417(8) Uani 1 1 d . . . . .
C6 C 0.2156(5) 0.3195(4) 0.3119(3) 0.0467(9) Uani 1 1 d . . . . .
H6 H 0.3193 0.3849 0.3756 0.056 Uiso 1 1 calc R U . . .
C7 C 0.0265(5) 0.2439(4) 0.3350(3) 0.0497(9) Uani 1 1 d . . . . .
H7 H 0.0040 0.2568 0.4139 0.060 Uiso 1 1 calc R U . . .
C8 C 0.4573(5) 0.3788(4) 0.1672(3) 0.0421(8) Uani 1 1 d . . . . .
C9 C 0.6178(5) 0.5237(3) 0.2514(3) 0.0422(8) Uani 1 1 d . . . . .
C10 C 0.7566(5) 0.5808(4) 0.1621(3) 0.0534(9) Uani 1 1 d . . . . .
H10 H 0.6971 0.6376 0.1218 0.064 Uiso 1 1 calc R U . . .
C11 C 0.7210(5) 0.4354(4) 0.0693(3) 0.0569(10) Uani 1 1 d . . . . .
H11A H 0.7317 0.4523 -0.0099 0.068 Uiso 1 1 calc R U . . .
H11B H 0.8206 0.3952 0.0909 0.068 Uiso 1 1 calc R U . . .
C12 C 0.9748(6) 0.6779(4) 0.2096(4) 0.0705(12) Uani 1 1 d . . . . .
H12A H 1.0443 0.6956 0.1426 0.085 Uiso 1 1 calc R U . . .
H12B H 1.0368 0.6261 0.2528 0.085 Uiso 1 1 calc R U . . .
C13 C 0.5287(5) 0.6361(4) 0.3041(3) 0.0426(8) Uani 1 1 d . . . . .
C14 C 0.5179(7) 0.8124(4) 0.4721(3) 0.0767(13) Uani 1 1 d . . . . .
H14A H 0.5735 0.8944 0.4368 0.115 Uiso 1 1 calc R U . . .
H14B H 0.5641 0.8464 0.5578 0.115 Uiso 1 1 calc R U . . .
H14C H 0.3715 0.7747 0.4547 0.115 Uiso 1 1 calc R U . . .
Cl1 Cl 0.74643(14) 0.47161(11) 0.36446(8) 0.0617(3) Uani 1 1 d . . . . .
Cl2 Cl 1.00959(17) 0.85303(12) 0.30767(12) 0.0968(5) Uani 1 1 d . . . . .
N1 N 0.5146(4) 0.3319(3) 0.0702(2) 0.0525(8) Uani 1 1 d . . . . .
O1 O -0.3142(4) 0.0809(3) 0.2727(2) 0.0627(7) Uani 1 1 d . . . . .
O2 O 0.4192(4) 0.6673(3) 0.2399(2) 0.0582(7) Uani 1 1 d . . . . .
O3 O 0.5852(4) 0.6939(2) 0.42206(19) 0.0539(6) 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 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 O1 1.423(4) . ?
C2 C3 1.387(4) . ?
C2 C7 1.386(4) . ?
C2 O1 1.360(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.385(4) . ?
C5 C6 1.400(4) . ?
C5 C8 1.468(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.371(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.532(4) . ?
C8 N1 1.279(4) . ?
C9 C10 1.548(4) . ?
C9 C13 1.520(4) . ?
C9 Cl1 1.796(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.524(5) . ?
C10 C12 1.483(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 N1 1.465(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 Cl2 1.779(4) . ?
C13 O2 1.194(4) . ?
C13 O3 1.323(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 O3 1.454(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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
C7 C2 C3 119.3(3) . . ?
O1 C2 C3 124.8(3) . . ?
O1 C2 C7 115.9(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.9(3) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C6 117.4(3) . . ?
C4 C5 C8 120.1(3) . . ?
C6 C5 C8 122.5(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.2(3) . . ?
C6 C7 H7 119.9 . . ?
C5 C8 C9 123.5(3) . . ?
N1 C8 C5 122.7(3) . . ?
N1 C8 C9 113.8(3) . . ?
C8 C9 C10 100.2(2) . . ?
C8 C9 Cl1 107.2(2) . . ?
C10 C9 Cl1 111.9(2) . . ?
C13 C9 C8 113.0(3) . . ?
C13 C9 C10 110.8(3) . . ?
C13 C9 Cl1 113.0(2) . . ?
C9 C10 H10 107.1 . . ?
C11 C10 C9 101.9(3) . . ?
C11 C10 H10 107.1 . . ?
C12 C10 C9 118.7(3) . . ?
C12 C10 H10 107.1 . . ?
C12 C10 C11 114.2(3) . . ?
C10 C11 H11A 110.5 . . ?
C10 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
N1 C11 C10 106.0(3) . . ?
N1 C11 H11A 110.5 . . ?
N1 C11 H11B 110.5 . . ?
C10 C12 H12A 109.1 . . ?
C10 C12 H12B 109.1 . . ?
C10 C12 Cl2 112.7(3) . . ?
H12A C12 H12B 107.8 . . ?
Cl2 C12 H12A 109.1 . . ?
Cl2 C12 H12B 109.1 . . ?
O2 C13 C9 120.1(3) . . ?
O2 C13 O3 125.2(3) . . ?
O3 C13 C9 114.7(3) . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
C8 N1 C11 109.5(3) . . ?
C2 O1 C1 117.9(3) . . ?
C13 O3 C14 115.3(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
C2 C3 C4 C5 -0.6(5) . . . . ?
C3 C2 C7 C6 1.7(5) . . . . ?
C3 C2 O1 C1 -8.3(5) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
C3 C4 C5 C8 -179.5(3) . . . . ?
C4 C5 C6 C7 0.1(5) . . . . ?
C4 C5 C8 C9 158.9(3) . . . . ?
C4 C5 C8 N1 -21.2(5) . . . . ?
C5 C6 C7 C2 -1.4(5) . . . . ?
C5 C8 C9 C10 -161.6(3) . . . . ?
C5 C8 C9 C13 -43.7(4) . . . . ?
C5 C8 C9 Cl1 81.6(3) . . . . ?
C5 C8 N1 C11 179.4(3) . . . . ?
C6 C5 C8 C9 -21.5(5) . . . . ?
C6 C5 C8 N1 158.5(3) . . . . ?
C7 C2 C3 C4 -0.7(5) . . . . ?
C7 C2 O1 C1 172.0(3) . . . . ?
C8 C5 C6 C7 -179.6(3) . . . . ?
C8 C9 C10 C11 -26.8(3) . . . . ?
C8 C9 C10 C12 -153.2(3) . . . . ?
C8 C9 C13 O2 -49.3(4) . . . . ?
C8 C9 C13 O3 131.6(3) . . . . ?
C9 C8 N1 C11 -0.6(4) . . . . ?
C9 C10 C11 N1 28.3(3) . . . . ?
C9 C10 C12 Cl2 -64.7(4) . . . . ?
C9 C13 O3 C14 174.1(3) . . . . ?
C10 C9 C13 O2 62.3(4) . . . . ?
C10 C9 C13 O3 -116.9(3) . . . . ?
C10 C11 N1 C8 -18.1(4) . . . . ?
C11 C10 C12 Cl2 175.0(3) . . . . ?
C12 C10 C11 N1 157.6(3) . . . . ?
C13 C9 C10 C11 -146.3(3) . . . . ?
C13 C9 C10 C12 87.3(4) . . . . ?
Cl1 C9 C10 C11 86.5(3) . . . . ?
Cl1 C9 C10 C12 -39.9(4) . . . . ?
Cl1 C9 C13 O2 -171.3(3) . . . . ?
Cl1 C9 C13 O3 9.6(4) . . . . ?
N1 C8 C9 C10 18.4(4) . . . . ?
N1 C8 C9 C13 136.4(3) . . . . ?
N1 C8 C9 Cl1 -98.4(3) . . . . ?
O1 C2 C3 C4 179.6(3) . . . . ?
O1 C2 C7 C6 -178.6(3) . . . . ?
O2 C13 O3 C14 -4.9(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
