# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_ic19240
_database_code_depnum_ccdc_archive 'CCDC 2025408'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung Liu'
;National Taiwan University
Taiwan
;
_audit_update_record             
;
2020-08-26 deposited with the CCDC.	2020-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H25 Cl3 N2 O4 S'
_chemical_formula_weight         591.91

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.9981(3)
_cell_length_b                   15.1043(3)
_cell_length_c                   18.6398(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.173(2)
_cell_angle_gamma                90
_cell_volume                     2812.85(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6542
_cell_measurement_theta_min      3.2260
_cell_measurement_theta_max      29.0270

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.437
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97929
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2496
_diffrn_reflns_number            16245
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.910
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6303
_reflns_number_gt                4584
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0712P)²+2.2772P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6303
_refine_ls_number_parameters     370
_refine_ls_number_restraints     78
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1642
_refine_ls_wR_factor_gt          0.1445
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.110
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.71186(6) 0.60604(4) 0.54127(3) 0.03706(17) Uani 1 1 d . . . . .
O1 O 0.85373(18) 0.61274(12) 0.55115(10) 0.0468(5) Uani 1 1 d . . . . .
O2 O 0.65394(19) 0.53177(11) 0.50406(9) 0.0446(4) Uani 1 1 d . . . . .
O3 O 0.5176(2) 0.89530(12) 0.41268(10) 0.0517(5) Uani 1 1 d . . . . .
O4 O 0.3011(2) 0.85786(13) 0.40991(11) 0.0566(5) Uani 1 1 d . . . . .
N1 N 0.66249(19) 0.69502(13) 0.49559(10) 0.0329(4) Uani 1 1 d . . . . .
N2 N 0.2174(2) 0.79604(17) 0.44679(14) 0.0559(6) Uani 1 1 d . . . . .
C1 C 0.6398(3) 0.61382(16) 0.62558(13) 0.0373(5) Uani 1 1 d . . . . .
C2 C 0.5172(3) 0.57467(17) 0.63577(14) 0.0426(6) Uani 1 1 d . . . . .
H2A H 0.474639 0.540552 0.598676 0.051 Uiso 1 1 calc R U . . .
C3 C 0.4572(3) 0.5859(2) 0.70098(15) 0.0509(7) Uani 1 1 d . . . . .
H3A H 0.372681 0.559425 0.708305 0.061 Uiso 1 1 calc R U . . .
C4 C 0.5186(3) 0.6354(2) 0.75586(14) 0.0518(7) Uani 1 1 d . . . . .
C5 C 0.6415(3) 0.6734(2) 0.74410(14) 0.0522(7) Uani 1 1 d . . . . .
H5A H 0.684439 0.707092 0.781339 0.063 Uiso 1 1 calc R U . . .
C6 C 0.7035(3) 0.66372(19) 0.67955(14) 0.0453(6) Uani 1 1 d . . . . .
H6A H 0.787832 0.690555 0.672177 0.054 Uiso 1 1 calc R U . . .
C7 C 0.4517(4) 0.6462(3) 0.82676(17) 0.0784(11) Uani 1 1 d . . . . .
H7A H 0.365902 0.614744 0.824965 0.118 Uiso 1 1 calc R U . . .
H7B H 0.509580 0.621639 0.865427 0.118 Uiso 1 1 calc R U . . .
H7C H 0.436258 0.709215 0.835817 0.118 Uiso 1 1 calc R U . . .
C8 C 0.7182(2) 0.77846(15) 0.51934(12) 0.0332(5) Uani 1 1 d . . . . .
C9 C 0.8500(2) 0.79935(18) 0.50651(13) 0.0403(6) Uani 1 1 d . . . . .
H9A H 0.904063 0.759565 0.480786 0.048 Uiso 1 1 calc R U . . .
C10 C 0.9020(3) 0.87881(19) 0.53159(16) 0.0488(7) Uani 1 1 d . . . . .
H10A H 0.992771 0.893381 0.523804 0.059 Uiso 1 1 calc R U . . .
C11 C 0.8226(3) 0.93695(18) 0.56784(16) 0.0495(7) Uani 1 1 d . . . . .
H11A H 0.859275 0.991255 0.585191 0.059 Uiso 1 1 calc R U . . .
C12 C 0.6894(3) 0.91688(17) 0.57927(14) 0.0425(6) Uani 1 1 d . . . . .
H12A H 0.635130 0.957680 0.603804 0.051 Uiso 1 1 calc R U . . .
C13 C 0.6357(2) 0.83698(15) 0.55474(12) 0.0340(5) Uani 1 1 d . . . . .
C14 C 0.4909(2) 0.81109(15) 0.56263(12) 0.0345(5) Uani 1 1 d . . . . .
H14A H 0.487801 0.762397 0.598874 0.041 Uiso 1 1 calc R U . . .
C15 C 0.4379(2) 0.77359(15) 0.48873(12) 0.0346(5) Uani 1 1 d . . . . .
C16 C 0.5238(2) 0.69314(15) 0.46382(12) 0.0332(5) Uani 1 1 d . . . . .
H16A H 0.480371 0.638297 0.481921 0.040 Uiso 1 1 calc R U . . .
C17 C 0.4031(3) 0.88501(18) 0.58684(15) 0.0458(6) Uani 1 1 d . . . . .
H17A H 0.392959 0.935726 0.556983 0.055 Uiso 1 1 calc R U . . .
C18 C 0.3397(4) 0.8832(3) 0.6472(2) 0.0793(11) Uani 1 1 d . . . . .
H18A H 0.348205 0.833222 0.677987 0.095 Uiso 1 1 calc R U . . .
H18B H 0.285266 0.931767 0.660035 0.095 Uiso 1 1 calc R U . . .
C19 C 0.4317(3) 0.84826(17) 0.43377(13) 0.0421(6) Uani 1 1 d . . . . .
C20 C 0.2921(2) 0.74970(17) 0.48942(14) 0.0412(6) Uani 1 1 d . . . . .
C21 C 0.2307(3) 0.68140(19) 0.53530(18) 0.0551(7) Uani 1 1 d . . . . .
H21A H 0.300943 0.651956 0.564634 0.083 Uiso 1 1 calc R U . . .
H21B H 0.166902 0.709660 0.566703 0.083 Uiso 1 1 calc R U . . .
H21C H 0.183919 0.637562 0.504801 0.083 Uiso 1 1 calc R U . . .
C22 C 0.5230(3) 0.68605(16) 0.38271(13) 0.0390(6) Uani 1 1 d . . . . .
C23 C 0.4203(3) 0.64217(19) 0.34650(16) 0.0528(7) Uani 1 1 d . . . . .
H23A H 0.353154 0.613494 0.372770 0.063 Uiso 1 1 calc R U . . .
C24 C 0.4138(4) 0.6394(2) 0.27217(19) 0.0694(10) Uani 1 1 d . . . . .
H24A H 0.341713 0.609620 0.247847 0.083 Uiso 1 1 calc R U . . .
C25 C 0.5103(4) 0.6792(3) 0.23372(17) 0.0734(11) Uani 1 1 d . . . . .
H25A H 0.506541 0.676410 0.182766 0.088 Uiso 1 1 calc R U . . .
C26 C 0.6124(4) 0.7232(3) 0.26897(17) 0.0758(10) Uani 1 1 d . . . . .
H26A H 0.678971 0.751871 0.242285 0.091 Uiso 1 1 calc R U . . .
C27 C 0.6199(3) 0.7264(2) 0.34324(15) 0.0593(8) Uani 1 1 d . . . . .
H27A H 0.692063 0.756540 0.367178 0.071 Uiso 1 1 calc R U . . .
Cl1 Cl -0.1781(2) 0.56754(18) 0.34950(13) 0.0754(6) Uani 0.5 1 d . U P A 1
Cl2 Cl -0.0497(3) 0.4284(2) 0.2773(2) 0.1029(12) Uani 0.5 1 d . U P A 1
Cl3 Cl 0.1014(3) 0.5803(3) 0.3204(3) 0.1603(17) Uani 0.5 1 d . U P A 1
Cl1' Cl -0.1505(4) 0.5223(3) 0.3736(2) 0.1384(14) Uani 0.5 1 d . U P A 2
Cl2' Cl 0.0055(5) 0.4630(3) 0.2598(2) 0.1352(17) Uani 0.5 1 d . U P A 2
Cl3' Cl 0.0519(4) 0.6247(3) 0.3311(4) 0.195(2) Uani 0.5 1 d . U P A 2
C28 C -0.0137(4) 0.5134(2) 0.3397(2) 0.0749(10) Uani 1 1 d . U . . .
H28 H 0.012339 0.485001 0.386672 0.090 Uiso 1 1 calc R U . A 1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4270(19) . ?
S1 O2 1.4298(18) . ?
S1 N1 1.6561(19) . ?
S1 C1 1.757(3) . ?
O3 C19 1.193(3) . ?
O4 C19 1.371(3) . ?
O4 N2 1.445(3) . ?
N1 C8 1.441(3) . ?
N1 C16 1.487(3) . ?
N2 C20 1.278(3) . ?
C1 C2 1.381(4) . ?
C1 C6 1.392(3) . ?
C2 C3 1.386(4) . ?
C3 C4 1.390(4) . ?
C4 C5 1.381(4) . ?
C4 C7 1.512(4) . ?
C5 C6 1.382(4) . ?
C8 C9 1.384(3) . ?
C8 C13 1.392(3) . ?
C9 C10 1.382(4) . ?
C10 C11 1.378(4) . ?
C11 C12 1.390(4) . ?
C12 C13 1.391(3) . ?
C13 C14 1.512(3) . ?
C14 C17 1.500(3) . ?
C14 C15 1.563(3) . ?
C15 C20 1.503(3) . ?
C15 C19 1.523(3) . ?
C15 C16 1.569(3) . ?
C16 C22 1.515(3) . ?
C17 C18 1.312(4) . ?
C20 C21 1.487(4) . ?
C22 C23 1.377(4) . ?
C22 C27 1.381(4) . ?
C23 C24 1.385(4) . ?
C24 C25 1.364(6) . ?
C25 C26 1.365(5) . ?
C26 C27 1.385(4) . ?
Cl1 C28 1.852(4) . ?
Cl2 C28 1.761(5) . ?
Cl3 C28 1.583(5) . ?
Cl1' C28 1.534(5) . ?
Cl2' C28 1.690(6) . ?
Cl3' C28 1.813(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 120.03(11) . . ?
O1 S1 N1 106.52(11) . . ?
O2 S1 N1 106.26(10) . . ?
O1 S1 C1 108.60(11) . . ?
O2 S1 C1 108.30(12) . . ?
N1 S1 C1 106.33(10) . . ?
C19 O4 N2 109.81(19) . . ?
C8 N1 C16 118.89(18) . . ?
C8 N1 S1 116.58(14) . . ?
C16 N1 S1 116.39(15) . . ?
C20 N2 O4 108.3(2) . . ?
C2 C1 C6 121.1(2) . . ?
C2 C1 S1 119.37(19) . . ?
C6 C1 S1 119.4(2) . . ?
C1 C2 C3 118.9(2) . . ?
C2 C3 C4 121.2(3) . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 C7 121.3(3) . . ?
C3 C4 C7 120.2(3) . . ?
C4 C5 C6 121.7(3) . . ?
C5 C6 C1 118.6(3) . . ?
C9 C8 C13 121.5(2) . . ?
C9 C8 N1 120.4(2) . . ?
C13 C8 N1 118.1(2) . . ?
C10 C9 C8 119.2(2) . . ?
C11 C10 C9 120.2(3) . . ?
C10 C11 C12 120.6(2) . . ?
C11 C12 C13 119.9(2) . . ?
C12 C13 C8 118.6(2) . . ?
C12 C13 C14 123.5(2) . . ?
C8 C13 C14 118.0(2) . . ?
C17 C14 C13 114.2(2) . . ?
C17 C14 C15 110.6(2) . . ?
C13 C14 C15 107.56(19) . . ?
C20 C15 C19 99.7(2) . . ?
C20 C15 C14 112.09(19) . . ?
C19 C15 C14 109.16(19) . . ?
C20 C15 C16 111.03(19) . . ?
C19 C15 C16 112.55(19) . . ?
C14 C15 C16 111.75(18) . . ?
N1 C16 C22 111.64(19) . . ?
N1 C16 C15 112.33(18) . . ?
C22 C16 C15 111.57(18) . . ?
C18 C17 C14 123.3(3) . . ?
O3 C19 O4 121.3(2) . . ?
O3 C19 C15 130.6(2) . . ?
O4 C19 C15 108.1(2) . . ?
N2 C20 C21 119.6(3) . . ?
N2 C20 C15 114.0(2) . . ?
C21 C20 C15 126.4(2) . . ?
C23 C22 C27 118.5(3) . . ?
C23 C22 C16 119.9(2) . . ?
C27 C22 C16 121.5(2) . . ?
C22 C23 C24 120.7(3) . . ?
C25 C24 C23 120.4(3) . . ?
C24 C25 C26 119.5(3) . . ?
C25 C26 C27 120.6(4) . . ?
C22 C27 C26 120.3(3) . . ?
Cl1' C28 Cl2' 122.4(3) . . ?
Cl3 C28 Cl2 116.5(4) . . ?
Cl1' C28 Cl3' 106.6(3) . . ?
Cl2' C28 Cl3' 106.6(4) . . ?
Cl3 C28 Cl1 113.4(3) . . ?
Cl2 C28 Cl1 103.1(2) . . ?

_refine_diff_density_max         0.717
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.053



####################################################################### 
# 
# 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_ic19676
_database_code_depnum_ccdc_archive 'CCDC 2025409'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung Liu'
;National Taiwan University
Taiwan
;
_audit_update_record             
;
2020-08-26 deposited with the CCDC.	2020-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H27 Cl3 N2 O4 S'
_chemical_formula_weight         605.93

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   26.0749(9)
_cell_length_b                   9.8982(3)
_cell_length_c                   23.5410(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.383(4)
_cell_angle_gamma                90
_cell_volume                     5858.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4746
_cell_measurement_theta_min      3.4770
_cell_measurement_theta_max      27.9610

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             2512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.421
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96785
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2496
_diffrn_reflns_number            12733
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.129
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6486
_reflns_number_gt                4509
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0853P)²+16.4845P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6486
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_ref         0.1971
_refine_ls_wR_factor_gt          0.1700
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.004

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.71328(3) 0.74808(8) 0.67484(3) 0.0316(2) Uani 1 1 d . . . . .
O1 O 0.71004(10) 0.8898(2) 0.66260(10) 0.0442(6) Uani 1 1 d . . . . .
O2 O 0.76336(8) 0.6807(3) 0.68672(10) 0.0425(6) Uani 1 1 d . . . . .
O3 O 0.59270(9) 0.5067(3) 0.49468(9) 0.0391(6) Uani 1 1 d . . . . .
O4 O 0.61334(9) 0.2910(2) 0.51694(10) 0.0406(6) Uani 1 1 d . . . . .
N1 N 0.67404(9) 0.6700(2) 0.61720(10) 0.0263(5) Uani 1 1 d . . . . .
N2 N 0.63398(11) 0.2119(3) 0.56964(13) 0.0412(7) Uani 1 1 d . . . . .
C1 C 0.68400(12) 0.7173(3) 0.73297(13) 0.0313(7) Uani 1 1 d . . . . .
C2 C 0.70144(13) 0.6083(3) 0.77022(14) 0.0374(7) Uani 1 1 d . . . . .
H2A H 0.731138 0.556143 0.767021 0.045 Uiso 1 1 calc R U . . .
C3 C 0.67470(15) 0.5770(4) 0.81217(15) 0.0448(8) Uani 1 1 d . . . . .
H3A H 0.686573 0.503311 0.838183 0.054 Uiso 1 1 calc R U . . .
C4 C 0.63092(16) 0.6514(4) 0.81682(16) 0.0471(9) Uani 1 1 d . . . . .
C5 C 0.61479(16) 0.7605(4) 0.77929(16) 0.0494(9) Uani 1 1 d . . . . .
H5A H 0.585088 0.812754 0.782377 0.059 Uiso 1 1 calc R U . . .
C6 C 0.64122(14) 0.7947(4) 0.73736(15) 0.0407(8) Uani 1 1 d . . . . .
H6A H 0.630053 0.870089 0.712126 0.049 Uiso 1 1 calc R U . . .
C7 C 0.6016(2) 0.6142(5) 0.8620(2) 0.0731(14) Uani 1 1 d . . . . .
H7A H 0.572015 0.677007 0.859136 0.110 Uiso 1 1 calc R U . . .
H7B H 0.587854 0.521933 0.854639 0.110 Uiso 1 1 calc R U . . .
H7C H 0.626076 0.619494 0.901541 0.110 Uiso 1 1 calc R U . . .
C8 C 0.62042(11) 0.7211(3) 0.59646(12) 0.0268(6) Uani 1 1 d . . . . .
C9 C 0.61094(13) 0.8473(3) 0.57054(14) 0.0354(7) Uani 1 1 d . . . . .
H9A H 0.639492 0.900400 0.564763 0.042 Uiso 1 1 calc R U . . .
C10 C 0.55911(15) 0.8952(3) 0.55313(15) 0.0431(8) Uani 1 1 d . . . . .
H10A H 0.552133 0.982832 0.536381 0.052 Uiso 1 1 calc R U . . .
C11 C 0.51765(14) 0.8159(4) 0.56007(15) 0.0397(8) Uani 1 1 d . . . . .
H11A H 0.482261 0.849271 0.547969 0.048 Uiso 1 1 calc R U . . .
C12 C 0.52720(12) 0.6882(3) 0.58451(13) 0.0322(7) Uani 1 1 d . . . . .
H12A H 0.498351 0.633504 0.588336 0.039 Uiso 1 1 calc R U . . .
C13 C 0.57889(11) 0.6400(3) 0.60342(12) 0.0248(6) Uani 1 1 d . . . . .
C14 C 0.59360(11) 0.5013(3) 0.63041(12) 0.0245(6) Uani 1 1 d . . . . .
H14A H 0.614836 0.517088 0.671954 0.029 Uiso 1 1 calc R U . . .
C15 C 0.63257(11) 0.4376(3) 0.59768(12) 0.0248(6) Uani 1 1 d . . . . .
C16 C 0.68510(11) 0.5239(3) 0.61331(13) 0.0263(6) Uani 1 1 d . . . . .
H16A H 0.706030 0.494879 0.653461 0.032 Uiso 1 1 calc R U . . .
C17 C 0.71988(12) 0.4987(3) 0.57216(14) 0.0328(7) Uani 1 1 d . . . . .
C18 C 0.75612(14) 0.3932(4) 0.5833(2) 0.0484(9) Uani 1 1 d . . . . .
H18A H 0.759428 0.338275 0.617199 0.058 Uiso 1 1 calc R U . . .
C19 C 0.78747(17) 0.3672(4) 0.5456(2) 0.0665(13) Uani 1 1 d . . . . .
H19A H 0.812140 0.294505 0.553437 0.080 Uiso 1 1 calc R U . . .
C20 C 0.78279(19) 0.4477(5) 0.4962(2) 0.0705(14) Uani 1 1 d . . . . .
H20A H 0.804074 0.429599 0.470009 0.085 Uiso 1 1 calc R U . . .
C21 C 0.74742(17) 0.5533(4) 0.48521(19) 0.0564(11) Uani 1 1 d . . . . .
H21A H 0.744554 0.608906 0.451606 0.068 Uiso 1 1 calc R U . . .
C22 C 0.71593(14) 0.5790(4) 0.52296(15) 0.0418(8) Uani 1 1 d . . . . .
H22A H 0.691473 0.652175 0.515104 0.050 Uiso 1 1 calc R U . . .
C23 C 0.54665(11) 0.4140(3) 0.63388(13) 0.0301(6) Uani 1 1 d . . . . .
C24 C 0.53477(16) 0.4069(5) 0.68643(18) 0.0561(11) Uani 1 1 d . . . . .
H24A H 0.504792 0.356409 0.689957 0.067 Uiso 1 1 calc R U . . .
H24B H 0.556417 0.452479 0.719761 0.067 Uiso 1 1 calc R U . . .
C25 C 0.51483(14) 0.3462(4) 0.58141(18) 0.0463(9) Uani 1 1 d . . . . .
H25A H 0.530026 0.363923 0.548268 0.069 Uiso 1 1 calc R U . . .
H25B H 0.514795 0.248732 0.588636 0.069 Uiso 1 1 calc R U . . .
H25C H 0.478272 0.380411 0.572028 0.069 Uiso 1 1 calc R U . . .
C26 C 0.61002(11) 0.4241(3) 0.53137(13) 0.0296(6) Uani 1 1 d . . . . .
C27 C 0.64472(11) 0.2920(3) 0.61351(14) 0.0307(7) Uani 1 1 d . . . . .
C28 C 0.66566(15) 0.2385(4) 0.67401(16) 0.0451(8) Uani 1 1 d . . . . .
H28A H 0.671700 0.313406 0.702233 0.068 Uiso 1 1 calc R U . . .
H28B H 0.639849 0.175460 0.682865 0.068 Uiso 1 1 calc R U . . .
H28C H 0.699298 0.191253 0.676954 0.068 Uiso 1 1 calc R U . . .
Cl1 Cl 0.58840(8) 0.1426(2) 0.78434(7) 0.1080(6) Uani 1 1 d . . . . .
Cl2 Cl 0.57606(8) 0.00651(15) 0.88559(8) 0.1073(6) Uani 1 1 d . . . . .
Cl3 Cl 0.63239(8) 0.25339(17) 0.89874(10) 0.1188(6) Uani 1 1 d . . . . .
C29 C 0.6175(2) 0.1059(5) 0.8574(2) 0.0656(12) Uani 1 1 d . . . . .
H29A H 0.651304 0.055337 0.860330 0.079 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.427(2) . ?
S1 O1 1.430(2) . ?
S1 N1 1.658(2) . ?
S1 C1 1.761(3) . ?
O3 C26 1.188(4) . ?
O4 C26 1.368(4) . ?
O4 N2 1.445(4) . ?
N1 C8 1.445(4) . ?
N1 C16 1.482(4) . ?
N2 C27 1.273(4) . ?
C1 C6 1.380(5) . ?
C1 C2 1.388(5) . ?
C2 C3 1.387(5) . ?
C3 C4 1.387(5) . ?
C4 C5 1.388(6) . ?
C4 C7 1.510(5) . ?
C5 C6 1.387(5) . ?
C8 C9 1.383(4) . ?
C8 C13 1.392(4) . ?
C9 C10 1.388(5) . ?
C10 C11 1.380(5) . ?
C11 C12 1.384(5) . ?
C12 C13 1.387(4) . ?
C13 C14 1.518(4) . ?
C14 C23 1.518(4) . ?
C14 C15 1.562(4) . ?
C15 C27 1.501(4) . ?
C15 C26 1.521(4) . ?
C15 C16 1.573(4) . ?
C16 C17 1.513(4) . ?
C17 C18 1.386(5) . ?
C17 C22 1.386(5) . ?
C18 C19 1.381(6) . ?
C19 C20 1.387(7) . ?
C20 C21 1.373(7) . ?
C21 C22 1.384(5) . ?
C23 C24 1.354(5) . ?
C23 C25 1.456(5) . ?
C27 C28 1.481(5) . ?
Cl1 C29 1.725(5) . ?
Cl2 C29 1.719(5) . ?
Cl3 C29 1.740(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 120.01(15) . . ?
O2 S1 N1 106.05(13) . . ?
O1 S1 N1 107.56(13) . . ?
O2 S1 C1 109.26(15) . . ?
O1 S1 C1 108.16(15) . . ?
N1 S1 C1 104.76(13) . . ?
C26 O4 N2 110.0(2) . . ?
C8 N1 C16 120.5(2) . . ?
C8 N1 S1 116.43(19) . . ?
C16 N1 S1 114.67(19) . . ?
C27 N2 O4 108.1(3) . . ?
C6 C1 C2 121.3(3) . . ?
C6 C1 S1 119.2(3) . . ?
C2 C1 S1 119.2(2) . . ?
C1 C2 C3 118.7(3) . . ?
C4 C3 C2 121.2(3) . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 C7 120.4(4) . . ?
C5 C4 C7 120.9(4) . . ?
C6 C5 C4 121.3(3) . . ?
C5 C6 C1 118.8(3) . . ?
C9 C8 C13 121.3(3) . . ?
C9 C8 N1 120.6(3) . . ?
C13 C8 N1 118.1(3) . . ?
C10 C9 C8 119.0(3) . . ?
C9 C10 C11 120.2(3) . . ?
C12 C11 C10 120.6(3) . . ?
C11 C12 C13 120.0(3) . . ?
C12 C13 C8 118.9(3) . . ?
C12 C13 C14 124.1(3) . . ?
C8 C13 C14 116.9(2) . . ?
C23 C14 C13 114.8(2) . . ?
C23 C14 C15 115.9(2) . . ?
C13 C14 C15 106.5(2) . . ?
C27 C15 C26 99.7(2) . . ?
C27 C15 C14 112.8(2) . . ?
C26 C15 C14 114.6(2) . . ?
C27 C15 C16 110.5(2) . . ?
C26 C15 C16 111.3(2) . . ?
C14 C15 C16 107.8(2) . . ?
N1 C16 C17 111.1(2) . . ?
N1 C16 C15 111.9(2) . . ?
C17 C16 C15 113.2(2) . . ?
C18 C17 C22 119.1(3) . . ?
C18 C17 C16 119.8(3) . . ?
C22 C17 C16 121.1(3) . . ?
C19 C18 C17 120.6(4) . . ?
C18 C19 C20 119.7(4) . . ?
C21 C20 C19 120.1(4) . . ?
C20 C21 C22 120.1(4) . . ?
C21 C22 C17 120.4(4) . . ?
C24 C23 C25 122.3(3) . . ?
C24 C23 C14 117.5(3) . . ?
C25 C23 C14 120.2(3) . . ?
O3 C26 O4 121.3(3) . . ?
O3 C26 C15 130.9(3) . . ?
O4 C26 C15 107.9(3) . . ?
N2 C27 C28 120.2(3) . . ?
N2 C27 C15 114.2(3) . . ?
C28 C27 C15 125.6(3) . . ?
Cl2 C29 Cl1 110.5(3) . . ?
Cl2 C29 Cl3 109.6(3) . . ?
Cl1 C29 Cl3 110.8(3) . . ?

_refine_diff_density_max         0.843
_refine_diff_density_min         -0.911
_refine_diff_density_rms         0.069



####################################################################### 
# 
# 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_ic20223
_database_code_depnum_ccdc_archive 'CCDC 2025410'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung Liu'
;National Taiwan University
Taiwan
;
_audit_update_record             
;
2020-08-26 deposited with the CCDC.	2020-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 Cl N2 O3'
_chemical_formula_weight         382.83

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   22.788(4)
_cell_length_b                   9.8240(10)
_cell_length_c                   19.984(4)
_cell_angle_alpha                90
_cell_angle_beta                 123.49(3)
_cell_angle_gamma                90
_cell_volume                     3731.2(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5610
_cell_measurement_theta_min      4.1340
_cell_measurement_theta_max      29.3380

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             1600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.229
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.43017
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2496
_diffrn_reflns_number            22624
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.896
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4280
_reflns_number_gt                3131
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0791P)²+2.7034P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4280
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1691
_refine_ls_wR_factor_gt          0.1419
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.41901(3) -0.17401(6) 0.64517(4) 0.0471(2) Uani 1 1 d . . . . .
O1 O 0.24406(7) 0.56458(16) 0.61177(9) 0.0390(4) Uani 1 1 d . . . . .
O2 O 0.50499(7) 0.46038(16) 0.66805(9) 0.0398(4) Uani 1 1 d . . . . .
O3 O 0.46478(7) 0.57117(17) 0.55172(9) 0.0392(4) Uani 1 1 d . . . . .
N1 N 0.35728(9) 0.49555(17) 0.67581(10) 0.0288(4) Uani 1 1 d . . . . .
H1 H 0.3986(14) 0.494(3) 0.7187(16) 0.043 Uiso 1 1 d . U . . .
N2 N 0.39838(9) 0.6087(2) 0.48673(12) 0.0446(5) Uani 1 1 d . . . . .
C1 C 0.39865(11) -0.0009(2) 0.63661(13) 0.0313(5) Uani 1 1 d . . . . .
C2 C 0.36712(11) 0.0588(2) 0.56250(13) 0.0323(5) Uani 1 1 d . . . . .
H2A H 0.356858 0.006866 0.517144 0.039 Uiso 1 1 calc R U . . .
C3 C 0.35046(11) 0.1959(2) 0.55477(13) 0.0312(5) Uani 1 1 d . . . . .
H3A H 0.328226 0.237416 0.503412 0.037 Uiso 1 1 calc R U . . .
C4 C 0.36550(9) 0.2742(2) 0.62039(12) 0.0267(4) Uani 1 1 d . . . . .
C5 C 0.39617(11) 0.2114(2) 0.69375(13) 0.0346(5) Uani 1 1 d . . . . .
H5A H 0.406273 0.262928 0.739178 0.042 Uiso 1 1 calc R U . . .
C6 C 0.41277(12) 0.0724(2) 0.70253(14) 0.0373(5) Uani 1 1 d . . . . .
H6A H 0.433500 0.029484 0.753331 0.045 Uiso 1 1 calc R U . . .
C7 C 0.34570(10) 0.42481(19) 0.60534(12) 0.0268(4) Uani 1 1 d . . . . .
H7A H 0.293930 0.428448 0.564014 0.032 Uiso 1 1 calc R U . . .
C8 C 0.30444(10) 0.5655(2) 0.67183(12) 0.0291(4) Uani 1 1 d . . . . .
C9 C 0.32184(11) 0.6472(2) 0.74322(13) 0.0306(5) Uani 1 1 d . . . . .
C10 C 0.38726(11) 0.7075(2) 0.79368(13) 0.0357(5) Uani 1 1 d . . . . .
H10A H 0.423958 0.691859 0.785419 0.043 Uiso 1 1 calc R U . . .
C11 C 0.39899(14) 0.7904(2) 0.85594(15) 0.0443(6) Uani 1 1 d . . . . .
H11A H 0.443753 0.831557 0.890237 0.053 Uiso 1 1 calc R U . . .
C12 C 0.34610(15) 0.8134(3) 0.86847(16) 0.0499(6) Uani 1 1 d . . . . .
H12A H 0.354142 0.871290 0.910842 0.060 Uiso 1 1 calc R U . . .
C13 C 0.28132(15) 0.7520(3) 0.81908(17) 0.0515(7) Uani 1 1 d . . . . .
H13A H 0.244990 0.766801 0.828061 0.062 Uiso 1 1 calc R U . . .
C14 C 0.26911(12) 0.6694(2) 0.75686(15) 0.0403(5) Uani 1 1 d . . . . .
H14A H 0.224456 0.627421 0.723197 0.048 Uiso 1 1 calc R U . . .
C15 C 0.45390(11) 0.5010(2) 0.60512(13) 0.0304(4) Uani 1 1 d . . . . .
C16 C 0.38050(10) 0.49503(19) 0.56946(12) 0.0270(4) Uani 1 1 d . . . . .
C17 C 0.34915(11) 0.5604(2) 0.49688(13) 0.0337(5) Uani 1 1 d . . . . .
C18 C 0.27350(12) 0.5856(3) 0.43585(16) 0.0495(7) Uani 1 1 d . . . . .
H18A H 0.245066 0.542896 0.453078 0.074 Uiso 1 1 calc R U . . .
H18B H 0.264611 0.683853 0.429797 0.074 Uiso 1 1 calc R U . . .
H18C H 0.260844 0.546703 0.384364 0.074 Uiso 1 1 calc R U . . .
C19 C 0.39632(13) 0.6566(3) 0.41703(15) 0.0431(6) Uani 1 1 d . . . . .
H19A H 0.347343 0.651977 0.369507 0.052 Uiso 1 1 calc R U . . .
H19B H 0.425550 0.596187 0.407150 0.052 Uiso 1 1 calc R U . . .
C20 C 0.42256(13) 0.7995(3) 0.42742(16) 0.0462(6) Uani 1 1 d . . . . .
H20A H 0.401270 0.867731 0.440965 0.055 Uiso 1 1 calc R U . . .
C21 C 0.47302(14) 0.8354(3) 0.41888(16) 0.0485(6) Uani 1 1 d . . . . .
H21C H 0.495217 0.769262 0.405339 0.058 Uiso 1 1 calc R U . . .
H21A H 0.487672 0.927796 0.426173 0.058 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.746(2) . ?
O1 C8 1.229(2) . ?
O2 C15 1.217(2) . ?
O3 N2 1.394(2) . ?
O3 C15 1.403(3) . ?
N1 C8 1.350(3) . ?
N1 C7 1.458(3) . ?
N2 C17 1.333(3) . ?
N2 C19 1.446(3) . ?
C1 C2 1.371(3) . ?
C1 C6 1.375(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.390(3) . ?
C4 C5 1.374(3) . ?
C4 C7 1.527(3) . ?
C5 C6 1.402(3) . ?
C7 C16 1.499(3) . ?
C8 C9 1.488(3) . ?
C9 C14 1.388(3) . ?
C9 C10 1.390(3) . ?
C10 C11 1.384(3) . ?
C11 C12 1.378(4) . ?
C12 C13 1.382(4) . ?
C13 C14 1.379(4) . ?
C15 C16 1.412(3) . ?
C16 C17 1.372(3) . ?
C17 C18 1.483(3) . ?
C19 C20 1.495(3) . ?
C20 C21 1.301(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
N2 O3 C15 106.37(15) . . ?
C8 N1 C7 120.36(17) . . ?
C17 N2 O3 109.64(17) . . ?
C17 N2 C19 132.83(19) . . ?
O3 N2 C19 115.14(17) . . ?
C2 C1 C6 121.2(2) . . ?
C2 C1 Cl1 118.35(16) . . ?
C6 C1 Cl1 120.49(17) . . ?
C1 C2 C3 119.0(2) . . ?
C2 C3 C4 121.6(2) . . ?
C5 C4 C3 118.26(19) . . ?
C5 C4 C7 124.48(18) . . ?
C3 C4 C7 117.26(18) . . ?
C4 C5 C6 120.9(2) . . ?
C1 C6 C5 119.1(2) . . ?
N1 C7 C16 112.40(16) . . ?
N1 C7 C4 113.27(16) . . ?
C16 C7 C4 111.30(16) . . ?
O1 C8 N1 122.35(19) . . ?
O1 C8 C9 120.19(18) . . ?
N1 C8 C9 117.45(18) . . ?
C14 C9 C10 119.3(2) . . ?
C14 C9 C8 118.11(19) . . ?
C10 C9 C8 122.52(19) . . ?
C11 C10 C9 120.1(2) . . ?
C12 C11 C10 120.4(2) . . ?
C11 C12 C13 119.7(2) . . ?
C14 C13 C12 120.4(2) . . ?
C13 C14 C9 120.2(2) . . ?
O2 C15 O3 118.52(18) . . ?
O2 C15 C16 134.4(2) . . ?
O3 C15 C16 107.11(17) . . ?
C17 C16 C15 107.15(18) . . ?
C17 C16 C7 128.08(18) . . ?
C15 C16 C7 124.75(18) . . ?
N2 C17 C16 109.67(18) . . ?
N2 C17 C18 120.6(2) . . ?
C16 C17 C18 129.7(2) . . ?
N2 C19 C20 112.0(2) . . ?
C21 C20 C19 123.4(3) . . ?

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.065



