# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_15s01a37_ab03_
_database_code_depnum_ccdc_archive 'CCDC 2087464'
loop_
_audit_author_name
_audit_author_address
'Misaki Okayasu'
;Toho University
Japan
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C18 H15 N O3 S'
_chemical_formula_moiety         'C18 H15 N O3 S'
_chemical_formula_weight         325.38
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.79899(6)
_cell_length_b                   12.17385(9)
_cell_length_c                   15.22942(12)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1631.34(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19124
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      73.40
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.090
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680.00
_exptl_absorpt_coefficient_mu    1.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_T_max  0.844

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            20883
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_theta_max         68.187
_diffrn_reflns_theta_min         4.650
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2981
_reflns_number_gt                2969
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0745
_refine_ls_wR_factor_gt          0.0744
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2981
_refine_ls_number_parameters     268
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0505P)²+0.2918P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.48
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1242 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(6)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.62194(5) 0.74593(3) 0.57458(3) 0.01662(15) Uani 1 1 d . . . . .
O1 O 0.57268(17) 0.85777(11) 0.56627(10) 0.0231(3) Uani 1 1 d . . . . .
O2 O 0.78183(16) 0.72217(11) 0.58036(10) 0.0212(3) Uani 1 1 d . . . . .
O3 O 0.60150(19) 0.22516(11) 0.47600(10) 0.0252(3) Uani 1 1 d . . . . .
N1 N 0.5573(2) 0.68313(13) 0.48716(12) 0.0181(4) Uani 1 1 d . . . . .
H1 H 0.466(4) 0.705(2) 0.4767(19) 0.028(7) Uiso 1 1 d . . . . .
C1 C 0.5689(2) 0.56508(16) 0.48194(13) 0.0173(4) Uani 1 1 d . . . . .
C2 C 0.7098(2) 0.51584(17) 0.47097(14) 0.0207(4) Uani 1 1 d . . . . .
H2 H 0.795(4) 0.555(2) 0.4671(17) 0.029(7) Uiso 1 1 d . . . . .
C3 C 0.7199(2) 0.40170(17) 0.46676(14) 0.0226(4) Uani 1 1 d . . . . .
H3 H 0.821(3) 0.368(2) 0.4579(17) 0.026(7) Uiso 1 1 d . . . . .
C4 C 0.5892(2) 0.33955(16) 0.47284(13) 0.0213(4) Uani 1 1 d . . . . .
C5 C 0.4480(2) 0.38782(17) 0.48180(15) 0.0237(4) Uani 1 1 d . . . . .
H5 H 0.354(3) 0.341(2) 0.4880(18) 0.035(7) Uiso 1 1 d . . . . .
C6 C 0.4377(2) 0.50183(17) 0.48734(14) 0.0214(4) Uani 1 1 d . . . . .
H6 H 0.343(4) 0.535(2) 0.4953(17) 0.033(7) Uiso 1 1 d . . . . .
C7 C 0.5344(2) 0.68574(17) 0.66671(14) 0.0192(4) Uani 1 1 d . . . . .
C8 C 0.3961(3) 0.7267(2) 0.69580(17) 0.0325(5) Uani 1 1 d . . . . .
H8 H 0.347(3) 0.788(2) 0.6649(19) 0.037(8) Uiso 1 1 d . . . . .
C9 C 0.3269(3) 0.6772(2) 0.7671(2) 0.0430(7) Uani 1 1 d . . . . .
H9 H 0.244(4) 0.705(3) 0.791(3) 0.063(11) Uiso 1 1 d . . . . .
C10 C 0.3924(3) 0.5872(2) 0.80712(17) 0.0382(6) Uani 1 1 d . . . . .
H10 H 0.343(4) 0.550(2) 0.854(2) 0.041(8) Uiso 1 1 d . . . . .
C11 C 0.5276(3) 0.5454(2) 0.77656(17) 0.0365(6) Uani 1 1 d . . . . .
H11 H 0.578(4) 0.484(3) 0.803(2) 0.051(9) Uiso 1 1 d . . . . .
C12 C 0.6014(3) 0.59520(19) 0.70586(15) 0.0275(5) Uani 1 1 d . . . . .
H12 H 0.695(4) 0.568(2) 0.686(2) 0.042(8) Uiso 1 1 d . . . . .
C13 C 0.5724(2) 0.16610(16) 0.40008(13) 0.0187(4) Uani 1 1 d . . . . .
C14 C 0.5534(2) 0.05330(16) 0.41184(15) 0.0215(4) Uani 1 1 d . . . . .
H14 H 0.563(3) 0.020(2) 0.4716(19) 0.030(7) Uiso 1 1 d . . . . .
C15 C 0.5241(3) -0.01241(18) 0.33996(17) 0.0275(5) Uani 1 1 d . . . . .
H15 H 0.510(4) -0.088(3) 0.349(2) 0.048(9) Uiso 1 1 d . . . . .
C16 C 0.5124(3) 0.0331(2) 0.25689(17) 0.0342(6) Uani 1 1 d . . . . .
H16 H 0.489(3) -0.015(3) 0.203(2) 0.049(9) Uiso 1 1 d . . . . .
C17 C 0.5332(3) 0.1450(2) 0.24595(16) 0.0346(6) Uani 1 1 d . . . . .
H17 H 0.518(4) 0.180(3) 0.187(2) 0.047(9) Uiso 1 1 d . . . . .
C18 C 0.5647(3) 0.21221(18) 0.31738(15) 0.0259(5) Uani 1 1 d . . . . .
H18 H 0.577(3) 0.291(3) 0.310(2) 0.040(8) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.4345(14) . ?
S1 O2 1.4390(14) . ?
S1 N1 1.6372(18) . ?
S1 C7 1.760(2) . ?
O3 C13 1.385(2) . ?
O3 C4 1.398(2) . ?
N1 C1 1.443(2) . ?
N1 H1 0.86(3) . ?
C1 C2 1.387(3) . ?
C1 C6 1.390(3) . ?
C2 C3 1.394(3) . ?
C2 H2 0.89(3) . ?
C3 C4 1.380(3) . ?
C3 H3 0.99(3) . ?
C4 C5 1.381(3) . ?
C5 C6 1.393(3) . ?
C5 H5 1.01(3) . ?
C6 H6 0.93(3) . ?
C7 C12 1.385(3) . ?
C7 C8 1.387(3) . ?
C8 C9 1.383(4) . ?
C8 H8 0.98(3) . ?
C9 C10 1.380(4) . ?
C9 H9 0.88(4) . ?
C10 C11 1.375(4) . ?
C10 H10 0.95(3) . ?
C11 C12 1.396(3) . ?
C11 H11 0.96(3) . ?
C12 H12 0.93(3) . ?
C13 C18 1.380(3) . ?
C13 C14 1.395(3) . ?
C14 C15 1.380(3) . ?
C14 H14 1.00(3) . ?
C15 C16 1.385(4) . ?
C15 H15 0.93(3) . ?
C16 C17 1.384(3) . ?
C16 H16 1.03(3) . ?
C17 C18 1.389(3) . ?
C17 H17 1.00(4) . ?
C18 H18 0.97(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
O1 S1 O2 119.44(8) . . ?
O1 S1 N1 105.46(9) . . ?
O2 S1 N1 107.20(9) . . ?
O1 S1 C7 109.46(10) . . ?
O2 S1 C7 107.18(9) . . ?
N1 S1 C7 107.56(9) . . ?
C13 O3 C4 118.29(15) . . ?
C1 N1 S1 119.03(14) . . ?
C1 N1 H1 111.1(18) . . ?
S1 N1 H1 109.5(18) . . ?
C2 C1 C6 120.65(18) . . ?
C2 C1 N1 120.03(19) . . ?
C6 C1 N1 119.31(19) . . ?
C1 C2 C3 119.58(19) . . ?
C1 C2 H2 121.8(17) . . ?
C3 C2 H2 118.7(17) . . ?
C4 C3 C2 119.35(19) . . ?
C4 C3 H3 121.8(14) . . ?
C2 C3 H3 118.8(14) . . ?
C3 C4 C5 121.55(18) . . ?
C3 C4 O3 118.93(19) . . ?
C5 C4 O3 119.38(19) . . ?
C4 C5 C6 119.24(19) . . ?
C4 C5 H5 120.6(16) . . ?
C6 C5 H5 120.0(16) . . ?
C1 C6 C5 119.6(2) . . ?
C1 C6 H6 120.6(18) . . ?
C5 C6 H6 119.7(18) . . ?
C12 C7 C8 121.5(2) . . ?
C12 C7 S1 119.20(17) . . ?
C8 C7 S1 119.27(17) . . ?
C9 C8 C7 118.7(2) . . ?
C9 C8 H8 121.0(18) . . ?
C7 C8 H8 120.2(18) . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H9 118(3) . . ?
C8 C9 H9 121(3) . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 118.2(18) . . ?
C9 C10 H10 121.3(18) . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 123(2) . . ?
C12 C11 H11 117(2) . . ?
C7 C12 C11 118.6(2) . . ?
C7 C12 H12 121.2(19) . . ?
C11 C12 H12 120.2(19) . . ?
C18 C13 O3 124.02(18) . . ?
C18 C13 C14 120.77(19) . . ?
O3 C13 C14 115.20(18) . . ?
C15 C14 C13 119.4(2) . . ?
C15 C14 H14 119.9(16) . . ?
C13 C14 H14 120.7(16) . . ?
C14 C15 C16 120.4(2) . . ?
C14 C15 H15 119(2) . . ?
C16 C15 H15 121(2) . . ?
C17 C16 C15 119.6(2) . . ?
C17 C16 H16 119(2) . . ?
C15 C16 H16 121(2) . . ?
C16 C17 C18 120.8(2) . . ?
C16 C17 H17 120(2) . . ?
C18 C17 H17 119(2) . . ?
C13 C18 C17 119.0(2) . . ?
C13 C18 H18 120.1(18) . . ?
C17 C18 H18 120.9(18) . . ?

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
O1 S1 N1 C1 -171.09(16) . . . . ?
O2 S1 N1 C1 60.63(18) . . . . ?
C7 S1 N1 C1 -54.34(18) . . . . ?
S1 N1 C1 C2 -70.4(2) . . . . ?
S1 N1 C1 C6 110.1(2) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
N1 C1 C2 C3 179.45(19) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C2 C3 C4 O3 -174.67(18) . . . . ?
C13 O3 C4 C3 -101.5(2) . . . . ?
C13 O3 C4 C5 82.8(2) . . . . ?
C3 C4 C5 C6 -1.8(3) . . . . ?
O3 C4 C5 C6 173.71(19) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
N1 C1 C6 C5 179.60(19) . . . . ?
C4 C5 C6 C1 1.3(3) . . . . ?
O1 S1 C7 C12 -157.34(17) . . . . ?
O2 S1 C7 C12 -26.4(2) . . . . ?
N1 S1 C7 C12 88.57(19) . . . . ?
O1 S1 C7 C8 25.8(2) . . . . ?
O2 S1 C7 C8 156.72(18) . . . . ?
N1 S1 C7 C8 -88.29(19) . . . . ?
C12 C7 C8 C9 1.9(4) . . . . ?
S1 C7 C8 C9 178.6(2) . . . . ?
C7 C8 C9 C10 -1.6(4) . . . . ?
C8 C9 C10 C11 0.0(5) . . . . ?
C9 C10 C11 C12 1.3(4) . . . . ?
C8 C7 C12 C11 -0.5(4) . . . . ?
S1 C7 C12 C11 -177.32(19) . . . . ?
C10 C11 C12 C7 -1.1(4) . . . . ?
C4 O3 C13 C18 14.9(3) . . . . ?
C4 O3 C13 C14 -166.33(19) . . . . ?
C18 C13 C14 C15 -1.1(3) . . . . ?
O3 C13 C14 C15 -179.92(19) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C17 1.3(4) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
O3 C13 C18 C17 -179.3(2) . . . . ?
C14 C13 C18 C17 1.9(3) . . . . ?
C16 C17 C18 C13 -1.2(4) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O2 . . 3_466 2.874(2) 0.857 2.045 162.3 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_ana005_1a_s01a37N
_database_code_depnum_ccdc_archive 'CCDC 2087465'
loop_
_audit_author_name
_audit_author_address
'Misaki Okayasu'
;Toho University
Japan
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C56 H46 N6 O6 S2'
_chemical_formula_moiety         'C56 H46 N6 O6 S2'
_chemical_formula_weight         963.14
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   14.8313(5)
_cell_length_b                   16.0368(7)
_cell_length_c                   20.2334(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.974(3)
_cell_angle_gamma                90.0000
_cell_volume                     4809.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11380
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      29.54
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2016.00
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.780
_exptl_absorpt_correction_T_max  0.990

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            77886
_diffrn_reflns_av_unetI/netI     0.1052
_diffrn_reflns_av_R_equivalents  0.1335
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.540
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             11010
_reflns_number_gt                7152
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1376
_refine_ls_wR_factor_gt          0.1190
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         11010
_refine_ls_number_parameters     639
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0481P)²+0.6253P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.51
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.63364(4) 0.80752(3) 0.38649(3) 0.01795(14) Uani 1 1 d . . . . .
S2 S 0.39327(4) 0.32818(3) 0.32265(3) 0.01716(14) Uani 1 1 d . . . . .
O1 O 0.67549(10) 0.82625(9) 0.44975(7) 0.0216(4) Uani 1 1 d . . . . .
O2 O 0.68649(10) 0.81391(9) 0.32818(7) 0.0224(4) Uani 1 1 d . . . . .
O3 O 0.25333(11) 0.87782(12) 0.53787(8) 0.0323(4) Uani 1 1 d . . . . .
O4 O 0.33701(10) 0.34700(9) 0.26548(7) 0.0214(4) Uani 1 1 d . . . . .
O5 O 0.36125(10) 0.35009(9) 0.38675(7) 0.0213(4) Uani 1 1 d . . . . .
O6 O 0.78886(10) 0.40523(10) 0.48157(8) 0.0253(4) Uani 1 1 d . . . . .
N1 N 0.54824(12) 0.87054(11) 0.37318(10) 0.0183(4) Uani 1 1 d . . . . .
N2 N 0.48152(13) 0.85644(12) 0.23298(10) 0.0246(5) Uani 1 1 d . . . . .
N3 N 0.39411(14) 0.88924(15) -0.11470(10) 0.0363(6) Uani 1 1 d . . . . .
N4 N 0.48803(12) 0.37370(11) 0.31006(10) 0.0180(4) Uani 1 1 d . . . . .
N5 N 0.51653(13) 0.38457(12) 0.17334(9) 0.0255(5) Uani 1 1 d . . . . .
N6 N 0.55995(15) 0.37363(15) -0.17603(11) 0.0384(6) Uani 1 1 d . . . . .
C1 C 0.47469(14) 0.87085(12) 0.41787(11) 0.0163(5) Uani 1 1 d . . . . .
C2 C 0.38816(15) 0.85352(13) 0.39350(11) 0.0209(5) Uani 1 1 d . . . . .
H2 H 0.378738 0.838035 0.348470 0.025 Uiso 1 1 calc R U . . .
C3 C 0.31547(15) 0.85865(14) 0.43440(11) 0.0219(5) Uani 1 1 d . . . . .
H3 H 0.255933 0.849322 0.417167 0.026 Uiso 1 1 calc R U . . .
C4 C 0.33025(15) 0.87746(14) 0.50049(11) 0.0219(5) Uani 1 1 d . . . . .
C5 C 0.41616(15) 0.89396(15) 0.52587(11) 0.0244(5) Uani 1 1 d . . . . .
H5 H 0.425774 0.906703 0.571417 0.029 Uiso 1 1 calc R U . . .
C6 C 0.48830(15) 0.89163(14) 0.48376(11) 0.0213(5) Uani 1 1 d . . . . .
H6 H 0.547358 0.904406 0.500410 0.026 Uiso 1 1 calc R U . . .
C7 C 0.58623(14) 0.70721(13) 0.39051(11) 0.0175(5) Uani 1 1 d . . . . .
C8 C 0.59182(15) 0.66272(14) 0.44947(11) 0.0205(5) Uani 1 1 d . . . . .
H8 H 0.624234 0.684321 0.487001 0.025 Uiso 1 1 calc R U . . .
C9 C 0.54887(16) 0.58599(14) 0.45216(11) 0.0232(5) Uani 1 1 d . . . . .
H9 H 0.553228 0.553932 0.491622 0.028 Uiso 1 1 calc R U . . .
C10 C 0.50014(16) 0.55593(14) 0.39836(11) 0.0231(5) Uani 1 1 d . . . . .
H10 H 0.469355 0.504196 0.401361 0.028 Uiso 1 1 calc R U . . .
C11 C 0.49560(17) 0.60073(14) 0.33958(12) 0.0254(5) Uani 1 1 d . . . . .
H11 H 0.462470 0.579213 0.302350 0.031 Uiso 1 1 calc R U . . .
C12 C 0.53914(16) 0.67641(14) 0.33525(11) 0.0220(5) Uani 1 1 d . . . . .
H12 H 0.536955 0.707028 0.295030 0.026 Uiso 1 1 calc R U . . .
C13 C 0.26373(15) 0.88834(15) 0.60651(11) 0.0216(5) Uani 1 1 d . . . . .
C14 C 0.26244(16) 0.81881(15) 0.64638(12) 0.0265(6) Uani 1 1 d . . . . .
H14 H 0.260092 0.764573 0.627515 0.032 Uiso 1 1 calc R U . . .
C15 C 0.26461(17) 0.82907(16) 0.71452(13) 0.0300(6) Uani 1 1 d . . . . .
H15 H 0.263151 0.781753 0.742704 0.036 Uiso 1 1 calc R U . . .
C16 C 0.26891(16) 0.90827(16) 0.74123(12) 0.0284(6) Uani 1 1 d . . . . .
H16 H 0.270028 0.915306 0.787867 0.034 Uiso 1 1 calc R U . . .
C17 C 0.27159(16) 0.97718(15) 0.70061(12) 0.0268(6) Uani 1 1 d . . . . .
H17 H 0.275525 1.031426 0.719358 0.032 Uiso 1 1 calc R U . . .
C18 C 0.26855(15) 0.96755(15) 0.63278(12) 0.0259(5) Uani 1 1 d . . . . .
H18 H 0.269774 1.014886 0.604591 0.031 Uiso 1 1 calc R U . . .
C19 C 0.54807(16) 0.85490(15) 0.18951(12) 0.0271(6) Uani 1 1 d . . . . .
H19 H 0.608572 0.852160 0.206373 0.032 Uiso 1 1 calc R U . . .
C20 C 0.53348(16) 0.85707(16) 0.12174(12) 0.0285(6) Uani 1 1 d . . . . .
H20 H 0.583218 0.855509 0.093408 0.034 Uiso 1 1 calc R U . . .
C21 C 0.44631(15) 0.86151(14) 0.09508(11) 0.0212(5) Uani 1 1 d . . . . .
C22 C 0.37696(16) 0.86188(15) 0.14013(12) 0.0265(6) Uani 1 1 d . . . . .
H22 H 0.315778 0.864074 0.124712 0.032 Uiso 1 1 calc R U . . .
C23 C 0.39767(17) 0.85904(16) 0.20690(12) 0.0299(6) Uani 1 1 d . . . . .
H23 H 0.349141 0.858922 0.236347 0.036 Uiso 1 1 calc R U . . .
C24 C 0.33238(18) 0.86009(18) -0.07433(13) 0.0384(7) Uani 1 1 d . . . . .
H24 H 0.275046 0.845766 -0.093423 0.046 Uiso 1 1 calc R U . . .
C25 C 0.34497(17) 0.84912(16) -0.00750(12) 0.0324(6) Uani 1 1 d . . . . .
H25 H 0.297441 0.828085 0.018021 0.039 Uiso 1 1 calc R U . . .
C26 C 0.42743(15) 0.86891(14) 0.02257(11) 0.0219(5) Uani 1 1 d . . . . .
C27 C 0.49207(17) 0.89998(19) -0.01862(12) 0.0395(7) Uani 1 1 d . . . . .
H27 H 0.549780 0.915245 -0.000698 0.047 Uiso 1 1 calc R U . . .
C28 C 0.47339(18) 0.9089(2) -0.08519(13) 0.0442(8) Uani 1 1 d . . . . .
H28 H 0.519498 0.930285 -0.111884 0.053 Uiso 1 1 calc R U . . .
C29 C 0.56484(15) 0.37357(13) 0.35442(11) 0.0171(5) Uani 1 1 d . . . . .
C30 C 0.56536(15) 0.33643(13) 0.41672(11) 0.0178(5) Uani 1 1 d . . . . .
H30 H 0.515021 0.304289 0.429431 0.021 Uiso 1 1 calc R U . . .
C31 C 0.63896(15) 0.34611(13) 0.46033(11) 0.0186(5) Uani 1 1 d . . . . .
H31 H 0.638892 0.321124 0.502899 0.022 Uiso 1 1 calc R U . . .
C32 C 0.71271(14) 0.39261(13) 0.44127(11) 0.0180(5) Uani 1 1 d . . . . .
C33 C 0.71453(14) 0.42639(14) 0.37842(11) 0.0196(5) Uani 1 1 d . . . . .
H33 H 0.766352 0.455696 0.364775 0.024 Uiso 1 1 calc R U . . .
C34 C 0.64059(15) 0.41730(14) 0.33558(11) 0.0200(5) Uani 1 1 d . . . . .
H34 H 0.641587 0.441281 0.292675 0.024 Uiso 1 1 calc R U . . .
C35 C 0.41541(14) 0.21986(13) 0.32296(11) 0.0173(5) Uani 1 1 d . . . . .
C36 C 0.47212(15) 0.18768(14) 0.27575(11) 0.0216(5) Uani 1 1 d . . . . .
H36 H 0.501370 0.223853 0.246102 0.026 Uiso 1 1 calc R U . . .
C37 C 0.48527(16) 0.10240(14) 0.27259(12) 0.0257(5) Uani 1 1 d . . . . .
H37 H 0.524211 0.079560 0.240968 0.031 Uiso 1 1 calc R U . . .
C38 C 0.44151(17) 0.05059(15) 0.31566(12) 0.0282(6) Uani 1 1 d . . . . .
H38 H 0.449321 -0.008068 0.312609 0.034 Uiso 1 1 calc R U . . .
C39 C 0.38645(16) 0.08302(14) 0.36316(11) 0.0247(5) Uani 1 1 d . . . . .
H39 H 0.357446 0.046667 0.392810 0.030 Uiso 1 1 calc R U . . .
C40 C 0.37351(15) 0.16849(14) 0.36759(11) 0.0213(5) Uani 1 1 d . . . . .
H40 H 0.336675 0.191313 0.400556 0.026 Uiso 1 1 calc R U . . .
C41 C 0.77976(15) 0.39366(14) 0.54992(11) 0.0207(5) Uani 1 1 d . . . . .
C42 C 0.81128(17) 0.32121(15) 0.57862(12) 0.0278(6) Uani 1 1 d . . . . .
H42 H 0.836264 0.278531 0.552319 0.033 Uiso 1 1 calc R U . . .
C43 C 0.80620(18) 0.31114(16) 0.64637(13) 0.0331(6) Uani 1 1 d . . . . .
H43 H 0.827520 0.261189 0.666726 0.040 Uiso 1 1 calc R U . . .
C44 C 0.77017(17) 0.37360(16) 0.68443(12) 0.0315(6) Uani 1 1 d . . . . .
H44 H 0.766300 0.366473 0.730860 0.038 Uiso 1 1 calc R U . . .
C45 C 0.73980(17) 0.44643(16) 0.65477(12) 0.0322(6) Uani 1 1 d . . . . .
H45 H 0.715925 0.489640 0.681108 0.039 Uiso 1 1 calc R U . . .
C46 C 0.74382(16) 0.45702(15) 0.58721(12) 0.0279(6) Uani 1 1 d . . . . .
H46 H 0.722331 0.506845 0.566742 0.033 Uiso 1 1 calc R U . . .
C47 C 0.44881(16) 0.40630(15) 0.13167(12) 0.0265(6) Uani 1 1 d . . . . .
H47 H 0.393821 0.424184 0.149787 0.032 Uiso 1 1 calc R U . . .
C48 C 0.45426(16) 0.40421(15) 0.06378(11) 0.0243(5) Uani 1 1 d . . . . .
H48 H 0.404085 0.420477 0.036290 0.029 Uiso 1 1 calc R U . . .
C49 C 0.53432(15) 0.37794(14) 0.03580(11) 0.0210(5) Uani 1 1 d . . . . .
C50 C 0.60421(16) 0.35524(15) 0.07896(11) 0.0260(6) Uani 1 1 d . . . . .
H50 H 0.659968 0.336988 0.062290 0.031 Uiso 1 1 calc R U . . .
C51 C 0.59298(16) 0.35908(16) 0.14636(12) 0.0285(6) Uani 1 1 d . . . . .
H51 H 0.641943 0.342834 0.175019 0.034 Uiso 1 1 calc R U . . .
C52 C 0.63145(19) 0.3757(2) -0.13391(13) 0.0443(8) Uani 1 1 d . . . . .
H52 H 0.689544 0.376607 -0.152264 0.053 Uiso 1 1 calc R U . . .
C53 C 0.62740(17) 0.37661(18) -0.06596(12) 0.0349(6) Uani 1 1 d . . . . .
H53 H 0.681172 0.378039 -0.039072 0.042 Uiso 1 1 calc R U . . .
C54 C 0.54329(16) 0.37540(14) -0.03722(11) 0.0225(5) Uani 1 1 d . . . . .
C55 C 0.46919(17) 0.37277(17) -0.08038(12) 0.0335(6) Uani 1 1 d . . . . .
H55 H 0.410193 0.371125 -0.063576 0.040 Uiso 1 1 calc R U . . .
C56 C 0.48038(18) 0.37250(18) -0.14769(13) 0.0372(7) Uani 1 1 d . . . . .
H56 H 0.427700 0.371439 -0.175755 0.045 Uiso 1 1 calc R U . . .
H1 H 0.528(2) 0.8665(17) 0.3304(16) 0.052(9) Uiso 1 1 d . . . . .
H4 H 0.4985(19) 0.3809(17) 0.2641(15) 0.048(8) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.4349(16) . ?
S1 O2 1.4425(16) . ?
S1 N1 1.6354(19) . ?
S1 C7 1.759(2) . ?
S2 O4 1.4349(15) . ?
S2 O5 1.4399(16) . ?
S2 N4 1.6117(19) . ?
S2 C35 1.768(2) . ?
O3 C4 1.390(3) . ?
O3 C13 1.402(3) . ?
O6 C32 1.385(3) . ?
O6 C41 1.406(3) . ?
N1 C1 1.441(3) . ?
N1 H1 0.91(3) . ?
N2 C23 1.335(3) . ?
N2 C19 1.345(3) . ?
N3 C24 1.332(3) . ?
N3 C28 1.338(3) . ?
N4 C29 1.426(3) . ?
N4 H4 0.96(3) . ?
N5 C47 1.335(3) . ?
N5 C51 1.339(3) . ?
N6 C56 1.330(3) . ?
N6 C52 1.338(3) . ?
C1 C6 1.382(3) . ?
C1 C2 1.387(3) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.389(3) . ?
C7 C8 1.390(3) . ?
C8 C9 1.387(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.373(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.377(3) . ?
C13 C18 1.378(3) . ?
C14 C15 1.388(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.380(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.381(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.398(3) . ?
C21 C26 1.489(3) . ?
C22 C23 1.376(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C25 1.370(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.384(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.385(3) . ?
C27 C28 1.373(4) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C34 1.389(3) . ?
C29 C30 1.394(3) . ?
C30 C31 1.388(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.389(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.383(3) . ?
C33 C34 1.382(3) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 C40 1.385(3) . ?
C35 C36 1.393(3) . ?
C36 C37 1.383(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.382(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.384(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.387(3) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 C42 1.374(3) . ?
C41 C46 1.383(3) . ?
C42 C43 1.385(3) . ?
C42 H42 0.9500 . ?
C43 C44 1.382(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.381(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.381(3) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 C48 1.379(3) . ?
C47 H47 0.9500 . ?
C48 C49 1.398(3) . ?
C48 H48 0.9500 . ?
C49 C50 1.381(3) . ?
C49 C54 1.488(3) . ?
C50 C51 1.381(3) . ?
C50 H50 0.9500 . ?
C51 H51 0.9500 . ?
C52 C53 1.378(4) . ?
C52 H52 0.9500 . ?
C53 C54 1.395(3) . ?
C53 H53 0.9500 . ?
C54 C55 1.381(3) . ?
C55 C56 1.378(3) . ?
C55 H55 0.9500 . ?
C56 H56 0.9500 . ?

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 118.95(9) . . ?
O1 S1 N1 109.04(10) . . ?
O2 S1 N1 105.13(10) . . ?
O1 S1 C7 108.15(10) . . ?
O2 S1 C7 109.41(10) . . ?
N1 S1 C7 105.33(10) . . ?
O4 S2 O5 118.30(9) . . ?
O4 S2 N4 105.27(10) . . ?
O5 S2 N4 110.39(10) . . ?
O4 S2 C35 108.20(9) . . ?
O5 S2 C35 107.67(10) . . ?
N4 S2 C35 106.43(10) . . ?
C4 O3 C13 118.35(17) . . ?
C32 O6 C41 117.11(17) . . ?
C1 N1 S1 119.84(15) . . ?
C1 N1 H1 111(2) . . ?
S1 N1 H1 110.0(19) . . ?
C23 N2 C19 115.9(2) . . ?
C24 N3 C28 114.9(2) . . ?
C29 N4 S2 125.59(16) . . ?
C29 N4 H4 117.4(17) . . ?
S2 N4 H4 112.4(17) . . ?
C47 N5 C51 116.8(2) . . ?
C56 N6 C52 114.9(2) . . ?
C6 C1 C2 119.6(2) . . ?
C6 C1 N1 121.2(2) . . ?
C2 C1 N1 119.2(2) . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 119.4(2) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 O3 114.95(19) . . ?
C5 C4 O3 124.1(2) . . ?
C4 C5 C6 119.1(2) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C5 120.5(2) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C12 C7 C8 121.5(2) . . ?
C12 C7 S1 118.61(17) . . ?
C8 C7 S1 119.81(17) . . ?
C9 C8 C7 118.4(2) . . ?
C9 C8 H8 120.8 . . ?
C7 C8 H8 120.8 . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.4(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 119.0(2) . . ?
C11 C12 H12 120.5 . . ?
C7 C12 H12 120.5 . . ?
C14 C13 C18 121.5(2) . . ?
C14 C13 O3 118.7(2) . . ?
C18 C13 O3 119.7(2) . . ?
C13 C14 C15 119.1(2) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 119.1(2) . . ?
C13 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
N2 C19 C20 123.7(2) . . ?
N2 C19 H19 118.1 . . ?
C20 C19 H19 118.1 . . ?
C19 C20 C21 120.0(2) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C20 C21 C22 116.4(2) . . ?
C20 C21 C26 121.9(2) . . ?
C22 C21 C26 121.7(2) . . ?
C23 C22 C21 119.7(2) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
N2 C23 C22 124.2(2) . . ?
N2 C23 H23 117.9 . . ?
C22 C23 H23 117.9 . . ?
N3 C24 C25 125.2(2) . . ?
N3 C24 H24 117.4 . . ?
C25 C24 H24 117.4 . . ?
C24 C25 C26 119.5(2) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C25 C26 C27 116.0(2) . . ?
C25 C26 C21 123.2(2) . . ?
C27 C26 C21 120.7(2) . . ?
C28 C27 C26 120.5(2) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
N3 C28 C27 123.9(3) . . ?
N3 C28 H28 118.0 . . ?
C27 C28 H28 118.0 . . ?
C34 C29 C30 119.0(2) . . ?
C34 C29 N4 117.57(19) . . ?
C30 C29 N4 123.3(2) . . ?
C31 C30 C29 120.4(2) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C30 C31 C32 119.5(2) . . ?
C30 C31 H31 120.2 . . ?
C32 C31 H31 120.2 . . ?
C33 C32 O6 116.27(19) . . ?
C33 C32 C31 120.4(2) . . ?
O6 C32 C31 123.29(19) . . ?
C34 C33 C32 119.7(2) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C33 C34 C29 120.9(2) . . ?
C33 C34 H34 119.6 . . ?
C29 C34 H34 119.6 . . ?
C40 C35 C36 121.4(2) . . ?
C40 C35 S2 119.96(17) . . ?
C36 C35 S2 118.55(17) . . ?
C37 C36 C35 119.2(2) . . ?
C37 C36 H36 120.4 . . ?
C35 C36 H36 120.4 . . ?
C38 C37 C36 119.7(2) . . ?
C38 C37 H37 120.2 . . ?
C36 C37 H37 120.2 . . ?
C37 C38 C39 120.9(2) . . ?
C37 C38 H38 119.6 . . ?
C39 C38 H38 119.6 . . ?
C38 C39 C40 120.2(2) . . ?
C38 C39 H39 119.9 . . ?
C40 C39 H39 119.9 . . ?
C35 C40 C39 118.6(2) . . ?
C35 C40 H40 120.7 . . ?
C39 C40 H40 120.7 . . ?
C42 C41 C46 121.5(2) . . ?
C42 C41 O6 119.0(2) . . ?
C46 C41 O6 119.4(2) . . ?
C41 C42 C43 119.2(2) . . ?
C41 C42 H42 120.4 . . ?
C43 C42 H42 120.4 . . ?
C44 C43 C42 120.2(2) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
C45 C44 C43 119.8(2) . . ?
C45 C44 H44 120.1 . . ?
C43 C44 H44 120.1 . . ?
C46 C45 C44 120.6(2) . . ?
C46 C45 H45 119.7 . . ?
C44 C45 H45 119.7 . . ?
C45 C46 C41 118.7(2) . . ?
C45 C46 H46 120.7 . . ?
C41 C46 H46 120.6 . . ?
N5 C47 C48 123.7(2) . . ?
N5 C47 H47 118.2 . . ?
C48 C47 H47 118.2 . . ?
C47 C48 C49 119.4(2) . . ?
C47 C48 H48 120.3 . . ?
C49 C48 H48 120.3 . . ?
C50 C49 C48 116.9(2) . . ?
C50 C49 C54 122.0(2) . . ?
C48 C49 C54 121.1(2) . . ?
C51 C50 C49 119.9(2) . . ?
C51 C50 H50 120.0 . . ?
C49 C50 H50 120.0 . . ?
N5 C51 C50 123.3(2) . . ?
N5 C51 H51 118.4 . . ?
C50 C51 H51 118.4 . . ?
N6 C52 C53 125.1(3) . . ?
N6 C52 H52 117.5 . . ?
C53 C52 H52 117.5 . . ?
C52 C53 C54 119.1(2) . . ?
C52 C53 H53 120.5 . . ?
C54 C53 H53 120.5 . . ?
C55 C54 C53 116.1(2) . . ?
C55 C54 C49 122.2(2) . . ?
C53 C54 C49 121.7(2) . . ?
C56 C55 C54 120.3(2) . . ?
C56 C55 H55 119.8 . . ?
C54 C55 H55 119.8 . . ?
N6 C56 C55 124.4(2) . . ?
N6 C56 H56 117.8 . . ?
C55 C56 H56 117.8 . . ?

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
O1 S1 N1 C1 -60.05(18) . . . . ?
O2 S1 N1 C1 171.35(16) . . . . ?
C7 S1 N1 C1 55.82(19) . . . . ?
O4 S2 N4 C29 178.92(17) . . . . ?
O5 S2 N4 C29 50.2(2) . . . . ?
C35 S2 N4 C29 -66.4(2) . . . . ?
S1 N1 C1 C6 61.5(3) . . . . ?
S1 N1 C1 C2 -121.3(2) . . . . ?
C6 C1 C2 C3 1.4(3) . . . . ?
N1 C1 C2 C3 -175.8(2) . . . . ?
C1 C2 C3 C4 -3.0(3) . . . . ?
C2 C3 C4 C5 2.2(3) . . . . ?
C2 C3 C4 O3 -177.5(2) . . . . ?
C13 O3 C4 C3 173.9(2) . . . . ?
C13 O3 C4 C5 -5.8(3) . . . . ?
C3 C4 C5 C6 0.2(4) . . . . ?
O3 C4 C5 C6 179.8(2) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
N1 C1 C6 C5 178.2(2) . . . . ?
C4 C5 C6 C1 -1.8(3) . . . . ?
O1 S1 C7 C12 177.94(17) . . . . ?
O2 S1 C7 C12 -51.1(2) . . . . ?
N1 S1 C7 C12 61.5(2) . . . . ?
O1 S1 C7 C8 1.8(2) . . . . ?
O2 S1 C7 C8 132.72(18) . . . . ?
N1 S1 C7 C8 -114.73(19) . . . . ?
C12 C7 C8 C9 0.0(3) . . . . ?
S1 C7 C8 C9 176.03(17) . . . . ?
C7 C8 C9 C10 -1.7(3) . . . . ?
C8 C9 C10 C11 2.2(4) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C10 C11 C12 C7 -0.8(4) . . . . ?
C8 C7 C12 C11 1.3(3) . . . . ?
S1 C7 C12 C11 -174.84(18) . . . . ?
C4 O3 C13 C14 -98.6(3) . . . . ?
C4 O3 C13 C18 85.9(3) . . . . ?
C18 C13 C14 C15 1.0(4) . . . . ?
O3 C13 C14 C15 -174.3(2) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
C14 C15 C16 C17 -0.4(4) . . . . ?
C15 C16 C17 C18 1.0(4) . . . . ?
C14 C13 C18 C17 -0.4(4) . . . . ?
O3 C13 C18 C17 174.9(2) . . . . ?
C16 C17 C18 C13 -0.6(4) . . . . ?
C23 N2 C19 C20 1.0(4) . . . . ?
N2 C19 C20 C21 0.3(4) . . . . ?
C19 C20 C21 C22 -1.2(3) . . . . ?
C19 C20 C21 C26 176.4(2) . . . . ?
C20 C21 C22 C23 0.9(3) . . . . ?
C26 C21 C22 C23 -176.8(2) . . . . ?
C19 N2 C23 C22 -1.4(4) . . . . ?
C21 C22 C23 N2 0.5(4) . . . . ?
C28 N3 C24 C25 -0.4(4) . . . . ?
N3 C24 C25 C26 -0.2(4) . . . . ?
C24 C25 C26 C27 0.7(4) . . . . ?
C24 C25 C26 C21 178.1(2) . . . . ?
C20 C21 C26 C25 160.3(2) . . . . ?
C22 C21 C26 C25 -22.2(4) . . . . ?
C20 C21 C26 C27 -22.5(4) . . . . ?
C22 C21 C26 C27 155.0(3) . . . . ?
C25 C26 C27 C28 -0.7(4) . . . . ?
C21 C26 C27 C28 -178.1(3) . . . . ?
C24 N3 C28 C27 0.4(4) . . . . ?
C26 C27 C28 N3 0.2(5) . . . . ?
S2 N4 C29 C34 -179.14(16) . . . . ?
S2 N4 C29 C30 -3.2(3) . . . . ?
C34 C29 C30 C31 2.8(3) . . . . ?
N4 C29 C30 C31 -173.07(19) . . . . ?
C29 C30 C31 C32 -0.5(3) . . . . ?
C41 O6 C32 C33 162.07(19) . . . . ?
C41 O6 C32 C31 -20.5(3) . . . . ?
C30 C31 C32 C33 -2.5(3) . . . . ?
C30 C31 C32 O6 -179.86(19) . . . . ?
O6 C32 C33 C34 -179.21(19) . . . . ?
C31 C32 C33 C34 3.3(3) . . . . ?
C32 C33 C34 C29 -1.0(3) . . . . ?
C30 C29 C34 C33 -2.0(3) . . . . ?
N4 C29 C34 C33 174.06(19) . . . . ?
O4 S2 C35 C40 -106.46(18) . . . . ?
O5 S2 C35 C40 22.5(2) . . . . ?
N4 S2 C35 C40 140.84(17) . . . . ?
O4 S2 C35 C36 70.68(19) . . . . ?
O5 S2 C35 C36 -160.39(17) . . . . ?
N4 S2 C35 C36 -42.0(2) . . . . ?
C40 C35 C36 C37 1.4(3) . . . . ?
S2 C35 C36 C37 -175.74(16) . . . . ?
C35 C36 C37 C38 0.6(3) . . . . ?
C36 C37 C38 C39 -1.7(3) . . . . ?
C37 C38 C39 C40 0.8(3) . . . . ?
C36 C35 C40 C39 -2.2(3) . . . . ?
S2 C35 C40 C39 174.83(16) . . . . ?
C38 C39 C40 C35 1.1(3) . . . . ?
C32 O6 C41 C42 102.1(2) . . . . ?
C32 O6 C41 C46 -81.3(3) . . . . ?
C46 C41 C42 C43 0.6(4) . . . . ?
O6 C41 C42 C43 177.1(2) . . . . ?
C41 C42 C43 C44 -0.3(4) . . . . ?
C42 C43 C44 C45 -0.5(4) . . . . ?
C43 C44 C45 C46 1.0(4) . . . . ?
C44 C45 C46 C41 -0.7(4) . . . . ?
C42 C41 C46 C45 -0.1(4) . . . . ?
O6 C41 C46 C45 -176.6(2) . . . . ?
C51 N5 C47 C48 -0.4(4) . . . . ?
N5 C47 C48 C49 0.2(4) . . . . ?
C47 C48 C49 C50 0.1(3) . . . . ?
C47 C48 C49 C54 -179.5(2) . . . . ?
C48 C49 C50 C51 0.0(3) . . . . ?
C54 C49 C50 C51 179.6(2) . . . . ?
C47 N5 C51 C50 0.5(4) . . . . ?
C49 C50 C51 N5 -0.4(4) . . . . ?
C56 N6 C52 C53 0.1(4) . . . . ?
N6 C52 C53 C54 -0.1(5) . . . . ?
C52 C53 C54 C55 0.4(4) . . . . ?
C52 C53 C54 C49 -178.8(2) . . . . ?
C50 C49 C54 C55 159.8(2) . . . . ?
C48 C49 C54 C55 -20.7(3) . . . . ?
C50 C49 C54 C53 -21.1(4) . . . . ?
C48 C49 C54 C53 158.5(2) . . . . ?
C53 C54 C55 C56 -0.8(4) . . . . ?
C49 C54 C55 C56 178.4(2) . . . . ?
C52 N6 C56 C55 -0.5(4) . . . . ?
C54 C55 C56 N6 0.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N2 . . . 2.981(3) 0.91(3) 2.07(3) 180(3) no
N4 H4 N5 . . . 2.818(3) 0.96(3) 1.87(3) 175(2) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_mfu353-4a
_database_code_depnum_ccdc_archive 'CCDC 2087474'
loop_
_audit_author_name
_audit_author_address
'Misaki Okayasu'
;Toho University
Japan
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C14 H14 Cl N O4 S'
_chemical_formula_moiety         'C14 H14 Cl N O4 S'
_chemical_formula_weight         327.78
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   8.4505(4)
_cell_length_b                   13.5240(6)
_cell_length_c                   13.0184(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 100.599(5)
_cell_angle_gamma                90.0000
_cell_volume                     1462.42(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6059
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      29.60
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680.00
_exptl_absorpt_coefficient_mu    0.418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.396
_exptl_absorpt_correction_T_max  0.988

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            23555
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.667
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3349
_reflns_number_gt                2589
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0900
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3349
_refine_ls_number_parameters     194
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0366P)²+0.8944P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.60
_refine_diff_density_min         -0.45
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.50258(7) 0.61406(4) 1.08212(4) 0.02256(15) Uani 1 1 d . . . . .
S1 S 0.55199(6) 0.89866(4) 0.79701(4) 0.01392(14) Uani 1 1 d . . . . .
O1 O 0.43180(17) 0.95584(10) 0.73019(11) 0.0187(3) Uani 1 1 d . . . . .
O2 O 0.64619(18) 0.94313(10) 0.88808(11) 0.0202(3) Uani 1 1 d . . . . .
O3 O 0.50115(17) 0.63780(10) 0.36160(11) 0.0164(3) Uani 1 1 d . . . . .
O4 O 0.35770(17) 0.80408(10) 0.37980(10) 0.0159(3) Uani 1 1 d . . . . .
N1 N 0.6812(2) 0.85974(13) 0.72705(14) 0.0141(4) Uani 1 1 d . . . . .
H1 H 0.761(3) 0.8418(16) 0.7661(18) 0.013(6) Uiso 1 1 d . . . . .
C1 C 0.6340(2) 0.80035(14) 0.63493(15) 0.0127(4) Uani 1 1 d . . . . .
C2 C 0.7120(2) 0.71227(15) 0.62519(16) 0.0153(4) Uani 1 1 d . . . . .
H2 H 0.793538 0.689902 0.680499 0.018 Uiso 1 1 calc R U . . .
C3 C 0.6716(2) 0.65575(14) 0.53426(15) 0.0142(4) Uani 1 1 d . . . . .
H3 H 0.726749 0.595579 0.527511 0.017 Uiso 1 1 calc R U . . .
C4 C 0.5511(2) 0.68733(14) 0.45391(15) 0.0134(4) Uani 1 1 d . . . . .
C5 C 0.4732(2) 0.77775(14) 0.46387(15) 0.0128(4) Uani 1 1 d . . . . .
C6 C 0.5148(2) 0.83423(14) 0.55299(15) 0.0133(4) Uani 1 1 d . . . . .
H6 H 0.462928 0.895765 0.558833 0.016 Uiso 1 1 calc R U . . .
C7 C 0.4540(2) 0.79327(14) 0.83556(15) 0.0132(4) Uani 1 1 d . . . . .
C8 C 0.3265(2) 0.75169(15) 0.76589(16) 0.0167(4) Uani 1 1 d . . . . .
H8 H 0.289116 0.781327 0.699716 0.020 Uiso 1 1 calc R U . . .
C9 C 0.2548(3) 0.66578(15) 0.79495(16) 0.0184(5) Uani 1 1 d . . . . .
H9 H 0.168682 0.636043 0.747898 0.022 Uiso 1 1 calc R U . . .
C10 C 0.3083(3) 0.62367(15) 0.89189(17) 0.0178(5) Uani 1 1 d . . . . .
H10 H 0.259375 0.565138 0.911592 0.021 Uiso 1 1 calc R U . . .
C11 C 0.4341(2) 0.66753(15) 0.96013(15) 0.0155(4) Uani 1 1 d . . . . .
C12 C 0.5086(2) 0.75246(14) 0.93361(15) 0.0139(4) Uani 1 1 d . . . . .
H12 H 0.594510 0.781961 0.981012 0.017 Uiso 1 1 calc R U . . .
C13 C 0.5710(3) 0.54254(15) 0.35166(17) 0.0191(5) Uani 1 1 d . . . . .
H13A H 0.526393 0.514601 0.282968 0.023 Uiso 1 1 calc R U . . .
H13B H 0.687974 0.549255 0.358711 0.023 Uiso 1 1 calc R U . . .
H13C H 0.546408 0.498595 0.406485 0.023 Uiso 1 1 calc R U . . .
C14 C 0.2928(3) 0.90165(14) 0.38083(16) 0.0179(4) Uani 1 1 d . . . . .
H14A H 0.212074 0.912059 0.317379 0.022 Uiso 1 1 calc R U . . .
H14B H 0.242391 0.909551 0.442368 0.022 Uiso 1 1 calc R U . . .
H14C H 0.379536 0.950225 0.383449 0.022 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C11 1.744(2) . ?
S1 O2 1.4331(15) . ?
S1 O1 1.4357(15) . ?
S1 N1 1.6325(18) . ?
S1 C7 1.767(2) . ?
O3 C4 1.373(2) . ?
O3 C13 1.433(2) . ?
O4 C5 1.373(2) . ?
O4 C14 1.430(2) . ?
N1 C1 1.437(3) . ?
N1 H1 0.81(2) . ?
C1 C2 1.379(3) . ?
C1 C6 1.403(3) . ?
C2 C3 1.398(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.406(3) . ?
C5 C6 1.379(3) . ?
C6 H6 0.9500 . ?
C7 C12 1.389(3) . ?
C7 C8 1.393(3) . ?
C8 C9 1.395(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(3) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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 119.91(9) . . ?
O2 S1 N1 105.67(9) . . ?
O1 S1 N1 107.87(9) . . ?
O2 S1 C7 108.76(9) . . ?
O1 S1 C7 106.87(9) . . ?
N1 S1 C7 107.16(9) . . ?
C4 O3 C13 116.90(16) . . ?
C5 O4 C14 116.71(15) . . ?
C1 N1 S1 122.26(15) . . ?
C1 N1 H1 115.5(16) . . ?
S1 N1 H1 108.5(16) . . ?
C2 C1 C6 120.06(18) . . ?
C2 C1 N1 119.69(18) . . ?
C6 C1 N1 120.16(18) . . ?
C1 C2 C3 120.27(18) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 120.12(18) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
O3 C4 C3 125.11(18) . . ?
O3 C4 C5 115.56(17) . . ?
C3 C4 C5 119.32(18) . . ?
O4 C5 C6 124.10(17) . . ?
O4 C5 C4 115.36(17) . . ?
C6 C5 C4 120.53(18) . . ?
C5 C6 C1 119.67(18) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C12 C7 C8 121.63(18) . . ?
C12 C7 S1 119.17(15) . . ?
C8 C7 S1 119.18(15) . . ?
C7 C8 C9 118.84(19) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 119.47(19) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 121.70(19) . . ?
C12 C11 Cl1 118.76(16) . . ?
C10 C11 Cl1 119.53(16) . . ?
C11 C12 C7 117.99(19) . . ?
C11 C12 H12 121.0 . . ?
C7 C12 H12 121.0 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
O2 S1 N1 C1 172.52(15) . . . . ?
O1 S1 N1 C1 -58.09(17) . . . . ?
C7 S1 N1 C1 56.66(18) . . . . ?
S1 N1 C1 C2 -127.37(18) . . . . ?
S1 N1 C1 C6 55.9(2) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
N1 C1 C2 C3 -177.46(18) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C13 O3 C4 C3 5.1(3) . . . . ?
C13 O3 C4 C5 -176.21(17) . . . . ?
C2 C3 C4 O3 -179.76(18) . . . . ?
C2 C3 C4 C5 1.6(3) . . . . ?
C14 O4 C5 C6 8.2(3) . . . . ?
C14 O4 C5 C4 -171.23(17) . . . . ?
O3 C4 C5 O4 0.0(2) . . . . ?
C3 C4 C5 O4 178.80(17) . . . . ?
O3 C4 C5 C6 -179.41(17) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
O4 C5 C6 C1 179.62(17) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C2 C1 C6 C5 1.7(3) . . . . ?
N1 C1 C6 C5 178.39(17) . . . . ?
O2 S1 C7 C12 -17.09(18) . . . . ?
O1 S1 C7 C12 -147.88(15) . . . . ?
N1 S1 C7 C12 96.70(17) . . . . ?
O2 S1 C7 C8 164.54(15) . . . . ?
O1 S1 C7 C8 33.75(18) . . . . ?
N1 S1 C7 C8 -81.67(18) . . . . ?
C12 C7 C8 C9 -1.4(3) . . . . ?
S1 C7 C8 C9 176.96(15) . . . . ?
C7 C8 C9 C10 0.8(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C9 C10 C11 Cl1 -179.60(16) . . . . ?
C10 C11 C12 C7 -0.1(3) . . . . ?
Cl1 C11 C12 C7 179.11(15) . . . . ?
C8 C7 C12 C11 1.0(3) . . . . ?
S1 C7 C12 C11 -177.33(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O3 . . 4_676 2.939(2) 0.806 2.191 154.5 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_izm_1c_s18a22N
_database_code_depnum_ccdc_archive 'CCDC 2087473'
loop_
_audit_author_name
_audit_author_address
'Misaki Okayasu'
;Toho University
Japan
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C17 H13 Br Cl N2 O2 S'
_chemical_formula_moiety         'C17 H13 Br Cl N2 O2 S'
_chemical_formula_weight         424.72
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.4205(5)
_cell_length_b                   9.8122(5)
_cell_length_c                   11.2928(6)
_cell_angle_alpha                93.998(4)
_cell_angle_beta                 101.829(5)
_cell_angle_gamma                108.500(5)
_cell_volume                     856.87(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7083
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      29.26
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             426.00
_exptl_absorpt_coefficient_mu    2.695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.763
_exptl_absorpt_correction_T_max  0.828

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            27568
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.628
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3929
_reflns_number_gt                3221
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0715
_refine_ls_wR_factor_gt          0.0673
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3929
_refine_ls_number_parameters     221
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0262P)²+0.1001P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.002
_refine_diff_density_max         0.48
_refine_diff_density_min         -0.57
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.27242(3) 0.67718(2) 0.75529(2) 0.02246(9) Uani 1 1 d . . . . .
Cl1 Cl 1.11398(7) 1.15503(6) 0.38822(6) 0.02967(15) Uani 1 1 d . . . . .
S1 S 0.46926(7) 0.78814(6) 0.17080(5) 0.01520(13) Uani 1 1 d . . . . .
O1 O 0.43982(19) 0.91962(16) 0.20682(14) 0.0187(3) Uani 1 1 d . . . . .
O2 O 0.42286(19) 0.72988(17) 0.04385(13) 0.0204(3) Uani 1 1 d . . . . .
N1 N 0.3671(2) 0.6575(2) 0.23582(17) 0.0186(4) Uani 1 1 d . . . . .
H1 H 0.309(4) 0.579(3) 0.186(2) 0.035(8) Uiso 1 1 d . . . . .
N2 N 0.1781(2) 0.38193(19) 0.09600(16) 0.0198(4) Uani 1 1 d . . . . .
C1 C 0.3553(3) 0.6652(2) 0.35916(19) 0.0156(5) Uani 1 1 d . . . . .
C2 C 0.2436(3) 0.5436(2) 0.3925(2) 0.0192(5) Uani 1 1 d . . . . .
H2 H 0.182811 0.459191 0.333867 0.023 Uiso 1 1 calc R U . . .
C3 C 0.2209(3) 0.5452(2) 0.5101(2) 0.0207(5) Uani 1 1 d . . . . .
H3 H 0.145037 0.462073 0.532587 0.025 Uiso 1 1 calc R U . . .
C4 C 0.3097(3) 0.6690(2) 0.59535(19) 0.0177(5) Uani 1 1 d . . . . .
C5 C 0.4255(3) 0.7888(2) 0.5645(2) 0.0190(5) Uani 1 1 d . . . . .
H5 H 0.488983 0.871897 0.624103 0.023 Uiso 1 1 calc R U . . .
C6 C 0.4481(3) 0.7866(2) 0.44639(19) 0.0178(5) Uani 1 1 d . . . . .
H6 H 0.527363 0.868416 0.424947 0.021 Uiso 1 1 calc R U . . .
C7 C 0.6916(3) 0.8187(2) 0.22862(19) 0.0158(5) Uani 1 1 d . . . . .
C8 C 0.8008(3) 0.9584(2) 0.28144(18) 0.0165(5) Uani 1 1 d . . . . .
H8 H 0.756849 1.035626 0.289742 0.020 Uiso 1 1 calc R U . . .
C9 C 0.9753(3) 0.9812(2) 0.3215(2) 0.0189(5) Uani 1 1 d . . . . .
C10 C 1.0409(3) 0.8709(3) 0.3099(2) 0.0237(5) Uani 1 1 d . . . . .
H10 H 1.161172 0.889246 0.337851 0.028 Uiso 1 1 calc R U . . .
C11 C 0.9301(3) 0.7321(3) 0.2571(2) 0.0252(5) Uani 1 1 d . . . . .
H11 H 0.974866 0.655354 0.248944 0.030 Uiso 1 1 calc R U . . .
C12 C 0.7544(3) 0.7052(2) 0.2161(2) 0.0213(5) Uani 1 1 d . . . . .
H12 H 0.678342 0.610476 0.179977 0.026 Uiso 1 1 calc R U . . .
C13 C 0.2763(3) 0.2991(3) 0.1021(2) 0.0278(6) Uani 1 1 d . . . . .
H13 H 0.397229 0.344904 0.132825 0.033 Uiso 1 1 calc R U . . .
C14 C 0.2138(3) 0.1505(3) 0.0668(2) 0.0248(5) Uani 1 1 d . . . . .
H14 H 0.290668 0.096920 0.073973 0.030 Uiso 1 1 calc R U . . .
C15 C 0.0373(3) 0.0798(2) 0.02039(18) 0.0153(5) Uani 1 1 d . . . . .
C16 C -0.0654(3) 0.1667(2) 0.0143(2) 0.0204(5) Uani 1 1 d . . . . .
H16 H -0.186803 0.124169 -0.015993 0.024 Uiso 1 1 calc R U . . .
C17 C 0.0084(3) 0.3147(2) 0.0521(2) 0.0205(5) Uani 1 1 d . . . . .
H17 H -0.064904 0.371488 0.046566 0.025 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C4 1.896(2) . ?
Cl1 C9 1.743(2) . ?
S1 O2 1.4314(15) . ?
S1 O1 1.4362(16) . ?
S1 N1 1.6164(19) . ?
S1 C7 1.771(2) . ?
N1 C1 1.415(3) . ?
N1 H1 0.86(3) . ?
N2 C13 1.327(3) . ?
N2 C17 1.337(3) . ?
C1 C6 1.389(3) . ?
C1 C2 1.395(3) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.386(3) . ?
C7 C8 1.393(3) . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.372(3) . ?
C10 C11 1.391(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.381(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(3) . ?
C15 C15 1.489(4) 2 ?
C16 C17 1.382(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

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 119.23(9) . . ?
O2 S1 N1 104.81(10) . . ?
O1 S1 N1 110.47(10) . . ?
O2 S1 C7 108.48(9) . . ?
O1 S1 C7 107.02(10) . . ?
N1 S1 C7 106.13(10) . . ?
C1 N1 S1 126.86(15) . . ?
C1 N1 H1 119.8(18) . . ?
S1 N1 H1 113.1(18) . . ?
C13 N2 C17 116.66(19) . . ?
C6 C1 C2 119.5(2) . . ?
C6 C1 N1 123.33(19) . . ?
C2 C1 N1 117.21(19) . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 Br1 119.06(16) . . ?
C3 C4 Br1 120.37(16) . . ?
C6 C5 C4 119.6(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C12 C7 C8 121.5(2) . . ?
C12 C7 S1 119.57(17) . . ?
C8 C7 S1 118.91(16) . . ?
C9 C8 C7 118.0(2) . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
C10 C9 C8 121.8(2) . . ?
C10 C9 Cl1 119.53(18) . . ?
C8 C9 Cl1 118.71(17) . . ?
C9 C10 C11 119.5(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C7 C12 C11 119.0(2) . . ?
C7 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
N2 C13 C14 124.2(2) . . ?
N2 C13 H13 117.9 . . ?
C14 C13 H13 117.9 . . ?
C13 C14 C15 119.5(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 116.2(2) . . ?
C16 C15 C15 121.9(2) . 2 ?
C14 C15 C15 121.9(3) . 2 ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
N2 C17 C16 123.2(2) . . ?
N2 C17 H17 118.4 . . ?
C16 C17 H17 118.4 . . ?

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
O2 S1 N1 C1 -172.61(18) . . . . ?
O1 S1 N1 C1 -43.0(2) . . . . ?
C7 S1 N1 C1 72.7(2) . . . . ?
S1 N1 C1 C6 -7.2(3) . . . . ?
S1 N1 C1 C2 172.63(17) . . . . ?
C6 C1 C2 C3 2.1(3) . . . . ?
N1 C1 C2 C3 -177.8(2) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 -2.4(3) . . . . ?
C2 C3 C4 Br1 176.98(17) . . . . ?
C3 C4 C5 C6 2.3(3) . . . . ?
Br1 C4 C5 C6 -177.10(17) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C2 C1 C6 C5 -2.2(3) . . . . ?
N1 C1 C6 C5 177.6(2) . . . . ?
O2 S1 C7 C12 -55.44(19) . . . . ?
O1 S1 C7 C12 174.70(16) . . . . ?
N1 S1 C7 C12 56.72(19) . . . . ?
O2 S1 C7 C8 121.98(17) . . . . ?
O1 S1 C7 C8 -7.87(19) . . . . ?
N1 S1 C7 C8 -125.86(17) . . . . ?
C12 C7 C8 C9 0.0(3) . . . . ?
S1 C7 C8 C9 -177.38(16) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C7 C8 C9 Cl1 -179.84(16) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
Cl1 C9 C10 C11 179.79(18) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C8 C7 C12 C11 -0.1(3) . . . . ?
S1 C7 C12 C11 177.25(18) . . . . ?
C10 C11 C12 C7 0.1(3) . . . . ?
C17 N2 C13 C14 -0.2(4) . . . . ?
N2 C13 C14 C15 0.5(4) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C13 C14 C15 C15 179.4(2) . . . 2 ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C15 C16 C17 -179.5(2) 2 . . . ?
C13 N2 C17 C16 0.1(3) . . . . ?
C15 C16 C17 N2 -0.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N2 . . . 2.825(2) 0.858 1.976 170.0 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_mit005_1d_s03a10N
_database_code_depnum_ccdc_archive 'CCDC 2087466'
loop_
_audit_author_name
_audit_author_address
'Misaki Okayasu'
;Toho University
Japan
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H23 N3 O3 S'
_chemical_formula_moiety         'C24 H23 N3 O3 S'
_chemical_formula_weight         433.52
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
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                   31.8179(11)
_cell_length_b                   8.1924(3)
_cell_length_c                   17.8610(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 103.002(3)
_cell_angle_gamma                90.0000
_cell_volume                     4536.4(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    19809
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      29.81
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1824.00
_exptl_absorpt_coefficient_mu    0.172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.150
_exptl_absorpt_correction_T_max  0.966

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            33592
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.572
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5214
_reflns_number_gt                4641
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1135
_refine_ls_wR_factor_gt          0.1102
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         5214
_refine_ls_number_parameters     284
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0468P)²+3.8061P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.60
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.37309(2) 0.13617(4) 0.65195(2) 0.01477(10) Uani 1 1 d . . . . .
O1 O 0.39538(3) 0.06024(11) 0.72222(5) 0.0183(2) Uani 1 1 d . . . . .
O2 O 0.32737(3) 0.10994(12) 0.62625(6) 0.0223(2) Uani 1 1 d . . . . .
O3 O 0.56461(3) 0.21372(13) 0.57455(6) 0.0257(2) Uani 1 1 d . . . . .
N1 N 0.39371(4) 0.07395(14) 0.58163(7) 0.0169(2) Uani 1 1 d . . . . .
N2 N 0.33238(4) 0.08929(19) 0.43930(7) 0.0309(3) Uani 1 1 d . . . . .
N3 N 0.18012(5) 0.0907(2) 0.08122(8) 0.0434(4) Uani 1 1 d . . . . .
C1 C 0.43731(4) 0.11279(15) 0.58009(7) 0.0160(3) Uani 1 1 d . . . . .
C2 C 0.44584(4) 0.20220(17) 0.51956(8) 0.0207(3) Uani 1 1 d . . . . .
H2 H 0.422523 0.240429 0.480483 0.025 Uiso 1 1 calc R U . . .
C3 C 0.48787(4) 0.23714(17) 0.51482(8) 0.0217(3) Uani 1 1 d . . . . .
H3 H 0.493261 0.297112 0.472427 0.026 Uiso 1 1 calc R U . . .
C4 C 0.52203(4) 0.18362(17) 0.57267(8) 0.0187(3) Uani 1 1 d . . . . .
C5 C 0.51379(4) 0.09413(17) 0.63392(8) 0.0209(3) Uani 1 1 d . . . . .
H5 H 0.537077 0.058023 0.673604 0.025 Uiso 1 1 calc R U . . .
C6 C 0.47182(4) 0.05739(16) 0.63736(8) 0.0192(3) Uani 1 1 d . . . . .
H6 H 0.466441 -0.005753 0.678832 0.023 Uiso 1 1 calc R U . . .
C7 C 0.38302(4) 0.34683(16) 0.66388(8) 0.0176(3) Uani 1 1 d . . . . .
C8 C 0.41147(5) 0.40047(17) 0.72972(8) 0.0245(3) Uani 1 1 d . . . . .
H8 H 0.426102 0.323968 0.766455 0.029 Uiso 1 1 calc R U . . .
C9 C 0.41855(6) 0.56731(19) 0.74187(9) 0.0365(4) Uani 1 1 d . . . . .
C10 C 0.39604(7) 0.67477(19) 0.68667(11) 0.0411(4) Uani 1 1 d . . . . .
H10 H 0.400058 0.788904 0.694593 0.049 Uiso 1 1 calc R U . . .
C11 C 0.36815(6) 0.62019(19) 0.62099(10) 0.0339(4) Uani 1 1 d . . . . .
H11 H 0.353519 0.696734 0.584283 0.041 Uiso 1 1 calc R U . . .
C12 C 0.36124(5) 0.45476(18) 0.60797(8) 0.0243(3) Uani 1 1 d . . . . .
H12 H 0.342318 0.416010 0.562521 0.029 Uiso 1 1 calc R U . . .
C13 C 0.57429(5) 0.2958(2) 0.51008(8) 0.0263(3) Uani 1 1 d . . . . .
H13A H 0.605576 0.310096 0.518220 0.032 Uiso 1 1 calc R U . . .
H13B H 0.563742 0.230855 0.463578 0.032 Uiso 1 1 calc R U . . .
H13C H 0.560217 0.402920 0.504141 0.032 Uiso 1 1 calc R U . . .
C14 C 0.44929(9) 0.6272(3) 0.81349(12) 0.0619(7) Uani 1 1 d . . . . .
H14A H 0.461826 0.533618 0.844849 0.074 Uiso 1 1 calc R U . . .
H14B H 0.472346 0.690957 0.799201 0.074 Uiso 1 1 calc R U . . .
H14C H 0.433672 0.696052 0.842999 0.074 Uiso 1 1 calc R U . . .
C15 C 0.29210(5) 0.1439(2) 0.43435(9) 0.0329(4) Uani 1 1 d . . . . .
H15 H 0.284590 0.180952 0.480034 0.040 Uiso 1 1 calc R U . . .
C16 C 0.26080(5) 0.1495(2) 0.36645(9) 0.0287(3) Uani 1 1 d . . . . .
H16 H 0.232654 0.188879 0.365938 0.034 Uiso 1 1 calc R U . . .
C17 C 0.27142(4) 0.09620(18) 0.29896(8) 0.0223(3) Uani 1 1 d . . . . .
C18 C 0.31313(5) 0.0394(2) 0.30374(8) 0.0269(3) Uani 1 1 d . . . . .
H18 H 0.321594 0.001764 0.259021 0.032 Uiso 1 1 calc R U . . .
C19 C 0.34217(5) 0.0382(2) 0.37412(9) 0.0293(3) Uani 1 1 d . . . . .
H19 H 0.370531 -0.000933 0.376324 0.035 Uiso 1 1 calc R U . . .
C20 C 0.16864(5) 0.0546(3) 0.14666(10) 0.0419(5) Uani 1 1 d . . . . .
H20 H 0.139400 0.025895 0.143891 0.050 Uiso 1 1 calc R U . . .
C21 C 0.19665(5) 0.0561(2) 0.21861(9) 0.0319(4) Uani 1 1 d . . . . .
H21 H 0.186594 0.029321 0.263303 0.038 Uiso 1 1 calc R U . . .
C22 C 0.23954(5) 0.09723(19) 0.22413(8) 0.0235(3) Uani 1 1 d . . . . .
C23 C 0.25193(5) 0.1352(2) 0.15648(9) 0.0315(4) Uani 1 1 d . . . . .
H23 H 0.280946 0.164211 0.157363 0.038 Uiso 1 1 calc R U . . .
C24 C 0.22133(6) 0.1301(3) 0.08748(9) 0.0406(4) Uani 1 1 d . . . . .
H24 H 0.230413 0.156482 0.041783 0.049 Uiso 1 1 calc R U . . .
H1 H 0.3755(7) 0.085(3) 0.5363(13) 0.048(6) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.4368(9) . ?
S1 O2 1.4398(10) . ?
S1 N1 1.6243(11) . ?
S1 C7 1.7588(13) . ?
O3 C4 1.3701(16) . ?
O3 C13 1.4256(17) . ?
N1 C1 1.4296(16) . ?
N1 H1 0.89(2) . ?
N2 C19 1.3383(19) . ?
N2 C15 1.3416(19) . ?
N3 C24 1.330(2) . ?
N3 C20 1.334(2) . ?
C1 C2 1.3826(19) . ?
C1 C6 1.3974(18) . ?
C2 C3 1.3888(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.3913(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3901(19) . ?
C5 C6 1.3837(19) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.384(2) . ?
C7 C12 1.3956(19) . ?
C8 C9 1.394(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.394(3) . ?
C9 C14 1.507(3) . ?
C10 C11 1.377(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.393(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.3907(19) . ?
C17 C22 1.4850(19) . ?
C18 C19 1.383(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.389(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.388(2) . ?
C23 C24 1.389(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

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 118.59(6) . . ?
O1 S1 N1 109.50(6) . . ?
O2 S1 N1 105.16(6) . . ?
O1 S1 C7 106.21(6) . . ?
O2 S1 C7 109.04(6) . . ?
N1 S1 C7 107.99(6) . . ?
C4 O3 C13 117.21(11) . . ?
C1 N1 S1 120.49(9) . . ?
C1 N1 H1 113.3(14) . . ?
S1 N1 H1 112.4(14) . . ?
C19 N2 C15 116.93(13) . . ?
C24 N3 C20 116.05(14) . . ?
C2 C1 C6 118.97(12) . . ?
C2 C1 N1 119.68(12) . . ?
C6 C1 N1 121.32(12) . . ?
C1 C2 C3 121.20(12) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C2 C3 C4 119.46(13) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
O3 C4 C5 115.87(12) . . ?
O3 C4 C3 124.36(12) . . ?
C5 C4 C3 119.77(12) . . ?
C6 C5 C4 120.30(12) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.28(13) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C8 C7 C12 122.09(13) . . ?
C8 C7 S1 118.66(10) . . ?
C12 C7 S1 119.23(11) . . ?
C7 C8 C9 119.68(14) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 118.03(16) . . ?
C10 C9 C14 121.79(16) . . ?
C8 C9 C14 120.17(16) . . ?
C11 C10 C9 121.86(15) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 120.58(15) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 117.75(15) . . ?
C11 C12 H12 121.1 . . ?
C7 C12 H12 121.1 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 C16 123.80(14) . . ?
N2 C15 H15 118.1 . . ?
C16 C15 H15 118.1 . . ?
C15 C16 C17 118.71(13) . . ?
C15 C16 H16 120.6 . . ?
C17 C16 H16 120.6 . . ?
C18 C17 C16 117.75(13) . . ?
C18 C17 C22 120.42(13) . . ?
C16 C17 C22 121.83(12) . . ?
C19 C18 C17 119.45(13) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
N2 C19 C18 123.36(13) . . ?
N2 C19 H19 118.3 . . ?
C18 C19 H19 118.3 . . ?
N3 C20 C21 124.29(16) . . ?
N3 C20 H20 117.9 . . ?
C21 C20 H20 117.9 . . ?
C22 C21 C20 118.93(14) . . ?
C22 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C21 C22 C23 117.39(13) . . ?
C21 C22 C17 121.62(13) . . ?
C23 C22 C17 120.97(13) . . ?
C22 C23 C24 119.08(15) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
N3 C24 C23 124.25(15) . . ?
N3 C24 H24 117.9 . . ?
C23 C24 H24 117.9 . . ?

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
O1 S1 N1 C1 -64.75(11) . . . . ?
O2 S1 N1 C1 166.80(10) . . . . ?
C7 S1 N1 C1 50.49(12) . . . . ?
S1 N1 C1 C2 -119.77(12) . . . . ?
S1 N1 C1 C6 62.46(15) . . . . ?
C6 C1 C2 C3 0.1(2) . . . . ?
N1 C1 C2 C3 -177.69(12) . . . . ?
C1 C2 C3 C4 -1.1(2) . . . . ?
C13 O3 C4 C5 175.96(12) . . . . ?
C13 O3 C4 C3 -4.4(2) . . . . ?
C2 C3 C4 O3 -178.74(13) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
O3 C4 C5 C6 179.96(12) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C4 C5 C6 C1 -1.3(2) . . . . ?
C2 C1 C6 C5 1.1(2) . . . . ?
N1 C1 C6 C5 178.85(12) . . . . ?
O1 S1 C7 C8 5.74(13) . . . . ?
O2 S1 C7 C8 134.60(11) . . . . ?
N1 S1 C7 C8 -111.64(12) . . . . ?
O1 S1 C7 C12 -172.58(10) . . . . ?
O2 S1 C7 C12 -43.71(12) . . . . ?
N1 S1 C7 C12 70.04(12) . . . . ?
C12 C7 C8 C9 0.8(2) . . . . ?
S1 C7 C8 C9 -177.48(12) . . . . ?
C7 C8 C9 C10 0.6(2) . . . . ?
C7 C8 C9 C14 179.71(18) . . . . ?
C8 C9 C10 C11 -1.3(3) . . . . ?
C14 C9 C10 C11 179.60(19) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C11 C12 C7 0.8(2) . . . . ?
C8 C7 C12 C11 -1.5(2) . . . . ?
S1 C7 C12 C11 176.80(11) . . . . ?
C19 N2 C15 C16 0.1(3) . . . . ?
N2 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C18 0.3(2) . . . . ?
C15 C16 C17 C22 179.51(16) . . . . ?
C16 C17 C18 C19 -0.2(2) . . . . ?
C22 C17 C18 C19 -179.43(15) . . . . ?
C15 N2 C19 C18 0.0(3) . . . . ?
C17 C18 C19 N2 0.0(3) . . . . ?
C24 N3 C20 C21 0.0(3) . . . . ?
N3 C20 C21 C22 -0.1(3) . . . . ?
C20 C21 C22 C23 0.1(3) . . . . ?
C20 C21 C22 C17 -178.09(16) . . . . ?
C18 C17 C22 C21 140.58(17) . . . . ?
C16 C17 C22 C21 -38.7(2) . . . . ?
C18 C17 C22 C23 -37.6(2) . . . . ?
C16 C17 C22 C23 143.20(17) . . . . ?
C21 C22 C23 C24 -0.1(2) . . . . ?
C17 C22 C23 C24 178.16(16) . . . . ?
C20 N3 C24 C23 0.0(3) . . . . ?
C22 C23 C24 N3 0.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N2 . . . 2.8380(16) 0.89(2) 1.95(2) 174(2) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_akt004_1d_s03a15N
_database_code_depnum_ccdc_archive 'CCDC 2087468'
loop_
_audit_author_name
_audit_author_address
'Misaki Okayasu'
;Toho University
Japan
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C23 H20 F N3 O2 S'
_chemical_formula_moiety         'C23 H20 F N3 O2 S'
_chemical_formula_weight         421.49
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.2247(6)
_cell_length_b                   13.3486(6)
_cell_length_c                   15.0139(13)
_cell_angle_alpha                90.0000
_cell_angle_beta                 98.168(7)
_cell_angle_gamma                90.0000
_cell_volume                     2028.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5124
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      28.52
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880.00
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.267
_exptl_absorpt_correction_T_max  0.992

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            31848
_diffrn_reflns_av_unetI/netI     0.0773
_diffrn_reflns_av_R_equivalents  0.0928
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.525
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4638
_reflns_number_gt                2687
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0632
_refine_ls_wR_factor_ref         0.1620
_refine_ls_wR_factor_gt          0.1393
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         4638
_refine_ls_number_parameters     275
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0608P)²+1.0180P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.41
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.67983(7) 0.50602(5) 0.68231(6) 0.0545(3) Uani 1 1 d . . . . .
F1 F 0.97777(18) 0.29737(15) 0.94097(15) 0.0729(6) Uani 1 1 d . . . . .
O1 O 0.6394(2) 0.56747(13) 0.60511(17) 0.0646(7) Uani 1 1 d . . . . .
O2 O 0.7219(2) 0.55168(13) 0.76796(17) 0.0615(6) Uani 1 1 d . . . . .
N1 N 0.8013(2) 0.43856(18) 0.6559(2) 0.0507(7) Uani 1 1 d . . . . .
N2 N 0.7867(2) 0.42077(18) 0.4650(2) 0.0588(7) Uani 1 1 d . . . . .
N3 N 0.6961(3) 0.4450(2) -0.0129(2) 0.0710(8) Uani 1 1 d . . . . .
C1 C 0.8715(2) 0.36478(19) 0.7097(2) 0.0452(8) Uani 1 1 d . . . . .
C2 C 0.8847(3) 0.3661(2) 0.8029(2) 0.0510(8) Uani 1 1 d . . . . .
H2 H 0.840936 0.414866 0.834002 0.061 Uiso 1 1 calc R U . . .
C3 C 0.9640(3) 0.2935(2) 0.8487(2) 0.0531(8) Uani 1 1 d . . . . .
C4 C 1.0296(3) 0.2216(2) 0.8088(3) 0.0551(9) Uani 1 1 d . . . . .
H4 H 1.084330 0.174214 0.843524 0.066 Uiso 1 1 calc R U . . .
C5 C 1.0141(3) 0.2200(2) 0.7167(3) 0.0520(8) Uani 1 1 d . . . . .
H5 H 1.058118 0.169985 0.687140 0.062 Uiso 1 1 calc R U . . .
C6 C 0.9352(3) 0.28985(19) 0.6655(2) 0.0478(8) Uani 1 1 d . . . . .
H6 H 0.924334 0.287118 0.601636 0.057 Uiso 1 1 calc R U . . .
C7 C 0.5515(3) 0.42076(18) 0.6958(2) 0.0448(8) Uani 1 1 d . . . . .
C8 C 0.4801(3) 0.37846(18) 0.6196(2) 0.0483(8) Uani 1 1 d . . . . .
H8 H 0.497156 0.397025 0.561227 0.058 Uiso 1 1 calc R U . . .
C9 C 0.3819(3) 0.30735(18) 0.6306(2) 0.0476(8) Uani 1 1 d . . . . .
C10 C 0.3606(3) 0.28282(19) 0.7173(2) 0.0494(8) Uani 1 1 d . . . . .
H10 H 0.295261 0.234425 0.725504 0.059 Uiso 1 1 calc R U . . .
C11 C 0.4315(3) 0.3267(2) 0.7910(2) 0.0495(8) Uani 1 1 d . . . . .
H11 H 0.414089 0.309283 0.849545 0.059 Uiso 1 1 calc R U . . .
C12 C 0.5289(3) 0.39660(18) 0.7808(2) 0.0480(8) Uani 1 1 d . . . . .
H12 H 0.578777 0.427041 0.831897 0.058 Uiso 1 1 calc R U . . .
C13 C 0.3019(3) 0.2589(2) 0.5513(2) 0.0598(9) Uani 1 1 d . . . . .
H13A H 0.329683 0.284705 0.495841 0.072 Uiso 1 1 calc R U . . .
H13B H 0.315313 0.186241 0.554483 0.072 Uiso 1 1 calc R U . . .
H13C H 0.208157 0.273996 0.551608 0.072 Uiso 1 1 calc R U . . .
C14 C 0.8402(3) 0.4940(2) 0.4206(3) 0.0547(9) Uani 1 1 d . . . . .
H14 H 0.892367 0.543025 0.455099 0.066 Uiso 1 1 calc R U . . .
C15 C 0.8242(2) 0.50248(19) 0.3293(2) 0.0475(8) Uani 1 1 d . . . . .
H15 H 0.864867 0.556033 0.301816 0.057 Uiso 1 1 calc R U . . .
C16 C 0.7484(2) 0.43245(18) 0.2766(2) 0.0440(8) Uani 1 1 d . . . . .
C17 C 0.6916(3) 0.3567(2) 0.3211(3) 0.0551(9) Uani 1 1 d . . . . .
H17 H 0.638121 0.307335 0.288091 0.066 Uiso 1 1 calc R U . . .
C18 C 0.7130(3) 0.3536(2) 0.4133(3) 0.0620(9) Uani 1 1 d . . . . .
H18 H 0.673417 0.300788 0.442467 0.074 Uiso 1 1 calc R U . . .
C19 C 0.6073(4) 0.4032(3) 0.0324(3) 0.0811(13) Uani 1 1 d . . . . .
H19 H 0.530540 0.374857 -0.001390 0.097 Uiso 1 1 calc R U . . .
C20 C 0.6190(3) 0.3981(2) 0.1245(3) 0.0642(10) Uani 1 1 d . . . . .
H20 H 0.551126 0.367622 0.152174 0.077 Uiso 1 1 calc R U . . .
C21 C 0.7298(3) 0.43755(18) 0.1774(2) 0.0481(8) Uani 1 1 d . . . . .
C22 C 0.8213(3) 0.4826(2) 0.1296(3) 0.0548(9) Uani 1 1 d . . . . .
H22 H 0.898632 0.512420 0.161218 0.066 Uiso 1 1 calc R U . . .
C23 C 0.8010(3) 0.4843(2) 0.0376(3) 0.0639(10) Uani 1 1 d . . . . .
H23 H 0.866145 0.515524 0.007797 0.077 Uiso 1 1 calc R U . . .
H1 H 0.790(3) 0.435(2) 0.601(2) 0.045(11) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.432(2) . ?
S1 O2 1.433(2) . ?
S1 N1 1.628(3) . ?
S1 C7 1.770(3) . ?
F1 C3 1.373(4) . ?
N1 C1 1.405(4) . ?
N1 H1 0.82(3) . ?
N2 C14 1.342(4) . ?
N2 C18 1.344(4) . ?
N3 C23 1.330(4) . ?
N3 C19 1.332(4) . ?
C1 C2 1.386(4) . ?
C1 C6 1.410(4) . ?
C2 C3 1.382(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.358(4) . ?
C4 C5 1.369(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.368(4) . ?
C7 C8 1.386(4) . ?
C8 C9 1.409(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(4) . ?
C9 C13 1.492(4) . ?
C10 C11 1.365(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.362(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(4) . ?
C16 C21 1.475(4) . ?
C17 C18 1.371(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.372(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.392(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.394(4) . ?
C22 C23 1.367(5) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

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 119.87(13) . . ?
O1 S1 N1 105.17(16) . . ?
O2 S1 N1 108.19(16) . . ?
O1 S1 C7 109.11(14) . . ?
O2 S1 C7 107.69(15) . . ?
N1 S1 C7 106.00(12) . . ?
C1 N1 S1 126.3(3) . . ?
C1 N1 H1 122(2) . . ?
S1 N1 H1 106(2) . . ?
C14 N2 C18 115.7(3) . . ?
C23 N3 C19 115.3(3) . . ?
C2 C1 N1 122.7(3) . . ?
C2 C1 C6 119.9(3) . . ?
N1 C1 C6 117.3(3) . . ?
C3 C2 C1 117.4(3) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C4 C3 F1 119.0(3) . . ?
C4 C3 C2 124.5(3) . . ?
F1 C3 C2 116.4(3) . . ?
C3 C4 C5 117.6(3) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 H4 121.2 . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 119.0(3) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C12 C7 C8 122.4(3) . . ?
C12 C7 S1 119.0(2) . . ?
C8 C7 S1 118.7(2) . . ?
C7 C8 C9 118.6(3) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C10 C9 C8 118.5(3) . . ?
C10 C9 C13 120.3(3) . . ?
C8 C9 C13 121.2(3) . . ?
C11 C10 C9 121.5(3) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 120.3(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 118.7(3) . . ?
C7 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 124.1(3) . . ?
N2 C14 H14 117.9 . . ?
C15 C14 H14 117.9 . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 117.1(3) . . ?
C17 C16 C21 121.2(3) . . ?
C15 C16 C21 121.7(3) . . ?
C18 C17 C16 119.5(3) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
N2 C18 C17 123.9(3) . . ?
N2 C18 H18 118.0 . . ?
C17 C18 H18 118.0 . . ?
N3 C19 C20 124.5(3) . . ?
N3 C19 H19 117.7 . . ?
C20 C19 H19 117.7 . . ?
C19 C20 C21 120.3(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C22 114.8(3) . . ?
C20 C21 C16 122.5(3) . . ?
C22 C21 C16 122.7(3) . . ?
C23 C22 C21 120.7(3) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
N3 C23 C22 124.3(3) . . ?
N3 C23 H23 117.8 . . ?
C22 C23 H23 117.8 . . ?

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
O1 S1 N1 C1 -178.4(2) . . . . ?
O2 S1 N1 C1 52.4(3) . . . . ?
C7 S1 N1 C1 -62.9(3) . . . . ?
S1 N1 C1 C2 -26.8(4) . . . . ?
S1 N1 C1 C6 156.1(2) . . . . ?
N1 C1 C2 C3 -175.4(2) . . . . ?
C6 C1 C2 C3 1.6(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C1 C2 C3 F1 178.8(2) . . . . ?
F1 C3 C4 C5 -179.9(2) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C2 C1 C6 C5 -2.1(4) . . . . ?
N1 C1 C6 C5 175.1(2) . . . . ?
O1 S1 C7 C12 -143.5(2) . . . . ?
O2 S1 C7 C12 -11.9(2) . . . . ?
N1 S1 C7 C12 103.7(2) . . . . ?
O1 S1 C7 C8 38.5(2) . . . . ?
O2 S1 C7 C8 170.10(19) . . . . ?
N1 S1 C7 C8 -74.3(2) . . . . ?
C12 C7 C8 C9 -0.7(4) . . . . ?
S1 C7 C8 C9 177.29(18) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C7 C8 C9 C13 -179.9(2) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C13 C9 C10 C11 -179.4(2) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C8 C7 C12 C11 0.4(4) . . . . ?
S1 C7 C12 C11 -177.50(18) . . . . ?
C10 C11 C12 C7 0.4(4) . . . . ?
C18 N2 C14 C15 -0.4(4) . . . . ?
N2 C14 C15 C16 0.2(4) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C14 C15 C16 C21 -179.1(2) . . . . ?
C15 C16 C17 C18 -0.6(4) . . . . ?
C21 C16 C17 C18 178.9(2) . . . . ?
C14 N2 C18 C17 0.2(4) . . . . ?
C16 C17 C18 N2 0.3(4) . . . . ?
C23 N3 C19 C20 -0.6(5) . . . . ?
N3 C19 C20 C21 -0.6(6) . . . . ?
C19 C20 C21 C22 1.5(4) . . . . ?
C19 C20 C21 C16 -178.9(3) . . . . ?
C17 C16 C21 C20 27.2(4) . . . . ?
C15 C16 C21 C20 -153.4(3) . . . . ?
C17 C16 C21 C22 -153.1(3) . . . . ?
C15 C16 C21 C22 26.3(4) . . . . ?
C20 C21 C22 C23 -1.3(4) . . . . ?
C16 C21 C22 C23 179.0(3) . . . . ?
C19 N3 C23 C22 0.7(5) . . . . ?
C21 C22 C23 N3 0.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N2 . . . 2.859(5) 0.82(3) 2.04(3) 173(3) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_16s03a46_ab1
_database_code_depnum_ccdc_archive 'CCDC 2087469'
loop_
_audit_author_name
_audit_author_address
'Misaki Okayasu'
;Toho University
Japan
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C15 H17 N O2 S'
_chemical_formula_moiety         'C15 H17 N O2 S'
_chemical_formula_weight         275.36
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.0097(5)
_cell_length_b                   12.3524(7)
_cell_length_c                   12.9152(7)
_cell_angle_alpha                82.341(5)
_cell_angle_beta                 84.612(5)
_cell_angle_gamma                84.720(5)
_cell_volume                     1413.62(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4642
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      28.21
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584.00
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.553
_exptl_absorpt_correction_T_max  0.998

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            45577
_diffrn_reflns_av_unetI/netI     0.1378
_diffrn_reflns_av_R_equivalents  0.1726
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.672
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             6479
_reflns_number_gt                3711
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1530
_refine_ls_R_factor_gt           0.0774
_refine_ls_wR_factor_ref         0.2176
_refine_ls_wR_factor_gt          0.1845
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         6479
_refine_ls_number_parameters     351
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1027P)²+1.5972P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.68
_refine_diff_density_min         -0.69
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.64355(11) 0.31677(8) 0.72909(8) 0.0188(3) Uani 1 1 d . . . . .
S2 S 0.15700(11) 0.16968(8) 0.75855(8) 0.0188(3) Uani 1 1 d . . . . .
O1 O 0.6735(3) 0.3086(2) 0.8370(2) 0.0234(7) Uani 1 1 d . . . . .
O2 O 0.4904(3) 0.3246(2) 0.7029(2) 0.0227(7) Uani 1 1 d . . . . .
O3 O 0.2143(3) 0.1732(2) 0.6510(2) 0.0234(7) Uani 1 1 d . . . . .
O4 O -0.0007(3) 0.1600(2) 0.7854(2) 0.0242(7) Uani 1 1 d . . . . .
N1 N 0.7266(4) 0.2074(3) 0.6863(3) 0.0205(8) Uani 1 1 d . . . . .
N2 N 0.1993(4) 0.2841(3) 0.7953(3) 0.0190(8) Uani 1 1 d . . . . .
C1 C 0.7263(5) 0.1833(3) 0.5804(3) 0.0198(9) Uani 1 1 d . . . . .
C2 C 0.5919(5) 0.1724(3) 0.5398(3) 0.0221(9) Uani 1 1 d . . . . .
H2A H 0.500126 0.183002 0.581169 0.027 Uiso 1 1 calc R U . . .
C3 C 0.5921(5) 0.1460(3) 0.4386(3) 0.0247(10) Uani 1 1 d . . . . .
C4 C 0.7280(5) 0.1286(3) 0.3804(3) 0.0257(10) Uani 1 1 d . . . . .
H4 H 0.727928 0.110564 0.311164 0.031 Uiso 1 1 calc R U . . .
C5 C 0.8647(5) 0.1367(3) 0.4205(3) 0.0263(10) Uani 1 1 d . . . . .
C6 C 0.8622(5) 0.1651(3) 0.5216(3) 0.0235(10) Uani 1 1 d . . . . .
H6 H 0.953398 0.172016 0.550675 0.028 Uiso 1 1 calc R U . . .
C7 C 0.7234(4) 0.4328(3) 0.6599(3) 0.0179(9) Uani 1 1 d . . . . .
C8 C 0.8723(4) 0.4485(3) 0.6721(3) 0.0179(9) Uani 1 1 d . . . . .
H8 H 0.929730 0.395604 0.715437 0.022 Uiso 1 1 calc R U . . .
C9 C 0.9365(5) 0.5417(3) 0.6206(3) 0.0211(9) Uani 1 1 d . . . . .
C10 C 0.8472(5) 0.6178(3) 0.5577(3) 0.0242(10) Uani 1 1 d . . . . .
H10 H 0.888860 0.681906 0.522330 0.029 Uiso 1 1 calc R U . . .
C11 C 0.7010(5) 0.6020(3) 0.5461(3) 0.0256(10) Uani 1 1 d . . . . .
H11 H 0.643734 0.654538 0.502290 0.031 Uiso 1 1 calc R U . . .
C12 C 0.6360(5) 0.5097(3) 0.5979(3) 0.0217(9) Uani 1 1 d . . . . .
H12 H 0.534344 0.499370 0.591098 0.026 Uiso 1 1 calc R U . . .
C13 C 0.4470(5) 0.1320(4) 0.3945(4) 0.0314(11) Uani 1 1 d . . . . .
H13A H 0.363298 0.147524 0.446018 0.038 Uiso 1 1 calc R U . . .
H13B H 0.436610 0.182906 0.330116 0.038 Uiso 1 1 calc R U . . .
H13C H 0.446668 0.056601 0.378815 0.038 Uiso 1 1 calc R U . . .
C14 C 1.0105(5) 0.1167(4) 0.3564(4) 0.0332(11) Uani 1 1 d . . . . .
H14A H 1.093590 0.126077 0.397323 0.040 Uiso 1 1 calc R U . . .
H14B H 1.019191 0.041866 0.337780 0.040 Uiso 1 1 calc R U . . .
H14C H 1.013613 0.169068 0.292331 0.040 Uiso 1 1 calc R U . . .
C15 C 1.0954(5) 0.5615(4) 0.6340(3) 0.0255(10) Uani 1 1 d . . . . .
H15A H 1.120701 0.630465 0.592168 0.031 Uiso 1 1 calc R U . . .
H15B H 1.106285 0.565795 0.708113 0.031 Uiso 1 1 calc R U . . .
H15C H 1.162796 0.501017 0.610533 0.031 Uiso 1 1 calc R U . . .
C16 C 0.1678(4) 0.3101(3) 0.9011(3) 0.0179(9) Uani 1 1 d . . . . .
C17 C 0.0206(4) 0.3210(3) 0.9450(3) 0.0196(9) Uani 1 1 d . . . . .
H17 H -0.059277 0.307469 0.906647 0.024 Uiso 1 1 calc R U . . .
C18 C -0.0089(5) 0.3519(3) 1.0452(3) 0.0211(9) Uani 1 1 d . . . . .
C19 C 0.1100(5) 0.3735(3) 1.0991(3) 0.0244(10) Uani 1 1 d . . . . .
H19 H 0.090350 0.395235 1.167189 0.029 Uiso 1 1 calc R U . . .
C20 C 0.2577(5) 0.3638(3) 1.0547(3) 0.0229(10) Uani 1 1 d . . . . .
C21 C 0.2853(5) 0.3307(3) 0.9558(3) 0.0203(9) Uani 1 1 d . . . . .
H21 H 0.385198 0.322018 0.925401 0.024 Uiso 1 1 calc R U . . .
C22 C 0.2509(5) 0.0588(3) 0.8331(3) 0.0197(9) Uani 1 1 d . . . . .
C23 C 0.4067(4) 0.0444(3) 0.8200(3) 0.0190(9) Uani 1 1 d . . . . .
H23 H 0.460828 0.095447 0.772943 0.023 Uiso 1 1 calc R U . . .
C24 C 0.4829(5) -0.0442(3) 0.8754(3) 0.0219(9) Uani 1 1 d . . . . .
C25 C 0.3995(5) -0.1154(3) 0.9464(3) 0.0255(10) Uani 1 1 d . . . . .
H25 H 0.449916 -0.175351 0.986445 0.031 Uiso 1 1 calc R U . . .
C26 C 0.2452(5) -0.1003(3) 0.9594(3) 0.0272(10) Uani 1 1 d . . . . .
H26 H 0.191220 -0.149984 1.008024 0.033 Uiso 1 1 calc R U . . .
C27 C 0.1681(5) -0.0130(3) 0.9021(3) 0.0219(9) Uani 1 1 d . . . . .
H27 H 0.062067 -0.002878 0.910030 0.026 Uiso 1 1 calc R U . . .
C28 C -0.1677(5) 0.3659(4) 1.0930(4) 0.0276(10) Uani 1 1 d . . . . .
H28A H -0.167629 0.387663 1.163252 0.033 Uiso 1 1 calc R U . . .
H28B H -0.224501 0.422650 1.048918 0.033 Uiso 1 1 calc R U . . .
H28C H -0.213980 0.296451 1.097954 0.033 Uiso 1 1 calc R U . . .
C29 C 0.3838(5) 0.3909(4) 1.1138(4) 0.0311(11) Uani 1 1 d . . . . .
H29A H 0.343169 0.412591 1.181748 0.037 Uiso 1 1 calc R U . . .
H29B H 0.455039 0.326390 1.124878 0.037 Uiso 1 1 calc R U . . .
H29C H 0.434993 0.451396 1.073033 0.037 Uiso 1 1 calc R U . . .
C30 C 0.6513(5) -0.0630(4) 0.8606(3) 0.0268(10) Uani 1 1 d . . . . .
H30A H 0.684675 -0.129084 0.905982 0.032 Uiso 1 1 calc R U . . .
H30B H 0.681640 -0.072396 0.787239 0.032 Uiso 1 1 calc R U . . .
H30C H 0.696717 0.000223 0.878926 0.032 Uiso 1 1 calc R U . . .
H1 H 0.800(5) 0.190(3) 0.713(3) 0.011(12) Uiso 1 1 d . . . . .
H2 H 0.295(5) 0.292(4) 0.762(4) 0.030(13) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.433(3) . ?
S1 O2 1.443(3) . ?
S1 N1 1.620(4) . ?
S1 C7 1.760(4) . ?
S2 O3 1.432(3) . ?
S2 O4 1.442(3) . ?
S2 N2 1.637(3) . ?
S2 C22 1.763(4) . ?
N1 C1 1.438(5) . ?
N1 H1 0.77(4) . ?
N2 C16 1.441(5) . ?
N2 H2 0.94(5) . ?
C1 C2 1.388(6) . ?
C1 C6 1.394(6) . ?
C2 C3 1.389(6) . ?
C2 H2A 0.9500 . ?
C3 C4 1.390(6) . ?
C3 C13 1.507(6) . ?
C4 C5 1.397(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(6) . ?
C5 C14 1.503(6) . ?
C6 H6 0.9500 . ?
C7 C12 1.393(6) . ?
C7 C8 1.399(6) . ?
C8 C9 1.396(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.404(6) . ?
C9 C15 1.504(6) . ?
C10 C11 1.374(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C21 1.387(5) . ?
C16 C17 1.395(6) . ?
C17 C18 1.392(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.395(6) . ?
C18 C28 1.508(6) . ?
C19 C20 1.400(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(6) . ?
C20 C29 1.513(6) . ?
C21 H21 0.9500 . ?
C22 C27 1.386(6) . ?
C22 C23 1.396(6) . ?
C23 C24 1.389(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.398(6) . ?
C24 C30 1.511(6) . ?
C25 C26 1.383(6) . ?
C25 H25 0.9500 . ?
C26 C27 1.393(6) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

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 119.05(17) . . ?
O1 S1 N1 105.81(18) . . ?
O2 S1 N1 107.36(19) . . ?
O1 S1 C7 108.94(17) . . ?
O2 S1 C7 106.22(18) . . ?
N1 S1 C7 109.22(19) . . ?
O3 S2 O4 119.09(17) . . ?
O3 S2 N2 105.26(18) . . ?
O4 S2 N2 107.96(18) . . ?
O3 S2 C22 109.15(19) . . ?
O4 S2 C22 106.32(18) . . ?
N2 S2 C22 108.75(18) . . ?
C1 N1 S1 124.2(3) . . ?
C1 N1 H1 116(3) . . ?
S1 N1 H1 110(3) . . ?
C16 N2 S2 122.9(3) . . ?
C16 N2 H2 119(3) . . ?
S2 N2 H2 102(3) . . ?
C2 C1 C6 120.7(4) . . ?
C2 C1 N1 119.9(4) . . ?
C6 C1 N1 119.3(4) . . ?
C1 C2 C3 119.8(4) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C4 C3 C2 119.1(4) . . ?
C4 C3 C13 120.7(4) . . ?
C2 C3 C13 120.2(4) . . ?
C3 C4 C5 122.1(4) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C4 C5 C6 118.0(4) . . ?
C4 C5 C14 121.2(4) . . ?
C6 C5 C14 120.8(4) . . ?
C1 C6 C5 120.3(4) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C12 C7 C8 121.2(4) . . ?
C12 C7 S1 119.7(3) . . ?
C8 C7 S1 119.1(3) . . ?
C9 C8 C7 120.1(4) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 118.0(4) . . ?
C8 C9 C15 121.1(4) . . ?
C10 C9 C15 120.9(4) . . ?
C11 C10 C9 121.7(4) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 120.6(4) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 118.5(4) . . ?
C11 C12 H12 120.7 . . ?
C7 C12 H12 120.7 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 C14 H14A 109.5 . . ?
C5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 120.6(4) . . ?
C21 C16 N2 118.9(4) . . ?
C17 C16 N2 120.4(3) . . ?
C18 C17 C16 119.8(4) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 119.0(4) . . ?
C17 C18 C28 120.4(4) . . ?
C19 C18 C28 120.5(4) . . ?
C18 C19 C20 121.2(4) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 H19 119.4 . . ?
C21 C20 C19 118.9(4) . . ?
C21 C20 C29 121.0(4) . . ?
C19 C20 C29 120.0(4) . . ?
C16 C21 C20 120.3(4) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C27 C22 C23 121.6(4) . . ?
C27 C22 S2 119.2(3) . . ?
C23 C22 S2 119.1(3) . . ?
C24 C23 C22 120.2(4) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 118.1(4) . . ?
C23 C24 C30 121.2(4) . . ?
C25 C24 C30 120.7(4) . . ?
C26 C25 C24 121.4(4) . . ?
C26 C25 H25 119.3 . . ?
C24 C25 H25 119.3 . . ?
C25 C26 C27 120.7(4) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C22 C27 C26 118.0(4) . . ?
C22 C27 H27 121.0 . . ?
C26 C27 H27 121.0 . . ?
C18 C28 H28A 109.5 . . ?
C18 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C18 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C20 C29 H29A 109.5 . . ?
C20 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C20 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C24 C30 H30A 109.5 . . ?
C24 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C24 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

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
O1 S1 N1 C1 -179.3(3) . . . . ?
O2 S1 N1 C1 52.6(4) . . . . ?
C7 S1 N1 C1 -62.2(4) . . . . ?
O3 S2 N2 C16 -176.7(3) . . . . ?
O4 S2 N2 C16 55.1(3) . . . . ?
C22 S2 N2 C16 -59.8(4) . . . . ?
S1 N1 C1 C2 -60.6(5) . . . . ?
S1 N1 C1 C6 123.0(4) . . . . ?
C6 C1 C2 C3 -1.8(6) . . . . ?
N1 C1 C2 C3 -178.1(4) . . . . ?
C1 C2 C3 C4 1.4(6) . . . . ?
C1 C2 C3 C13 179.0(4) . . . . ?
C2 C3 C4 C5 0.1(6) . . . . ?
C13 C3 C4 C5 -177.5(4) . . . . ?
C3 C4 C5 C6 -1.1(6) . . . . ?
C3 C4 C5 C14 179.5(4) . . . . ?
C2 C1 C6 C5 0.7(6) . . . . ?
N1 C1 C6 C5 177.1(4) . . . . ?
C4 C5 C6 C1 0.7(6) . . . . ?
C14 C5 C6 C1 -179.9(4) . . . . ?
O1 S1 C7 C12 -127.9(3) . . . . ?
O2 S1 C7 C12 1.4(4) . . . . ?
N1 S1 C7 C12 116.9(3) . . . . ?
O1 S1 C7 C8 49.2(4) . . . . ?
O2 S1 C7 C8 178.6(3) . . . . ?
N1 S1 C7 C8 -65.9(4) . . . . ?
C12 C7 C8 C9 -0.9(6) . . . . ?
S1 C7 C8 C9 -178.0(3) . . . . ?
C7 C8 C9 C10 0.3(6) . . . . ?
C7 C8 C9 C15 178.8(4) . . . . ?
C8 C9 C10 C11 -0.3(6) . . . . ?
C15 C9 C10 C11 -178.8(4) . . . . ?
C9 C10 C11 C12 0.8(6) . . . . ?
C10 C11 C12 C7 -1.3(6) . . . . ?
C8 C7 C12 C11 1.4(6) . . . . ?
S1 C7 C12 C11 178.4(3) . . . . ?
S2 N2 C16 C21 121.5(4) . . . . ?
S2 N2 C16 C17 -62.6(5) . . . . ?
C21 C16 C17 C18 -0.6(6) . . . . ?
N2 C16 C17 C18 -176.5(3) . . . . ?
C16 C17 C18 C19 1.3(6) . . . . ?
C16 C17 C18 C28 179.0(4) . . . . ?
C17 C18 C19 C20 -0.5(6) . . . . ?
C28 C18 C19 C20 -178.3(4) . . . . ?
C18 C19 C20 C21 -0.8(6) . . . . ?
C18 C19 C20 C29 178.2(4) . . . . ?
C17 C16 C21 C20 -0.8(6) . . . . ?
N2 C16 C21 C20 175.2(4) . . . . ?
C19 C20 C21 C16 1.5(6) . . . . ?
C29 C20 C21 C16 -177.6(4) . . . . ?
O3 S2 C22 C27 -131.2(3) . . . . ?
O4 S2 C22 C27 -1.6(4) . . . . ?
N2 S2 C22 C27 114.5(3) . . . . ?
O3 S2 C22 C23 47.7(4) . . . . ?
O4 S2 C22 C23 177.4(3) . . . . ?
N2 S2 C22 C23 -66.6(4) . . . . ?
C27 C22 C23 C24 0.9(6) . . . . ?
S2 C22 C23 C24 -178.0(3) . . . . ?
C22 C23 C24 C25 -2.1(6) . . . . ?
C22 C23 C24 C30 178.5(4) . . . . ?
C23 C24 C25 C26 1.7(6) . . . . ?
C30 C24 C25 C26 -178.9(4) . . . . ?
C24 C25 C26 C27 -0.2(6) . . . . ?
C23 C22 C27 C26 0.6(6) . . . . ?
S2 C22 C27 C26 179.5(3) . . . . ?
C25 C26 C27 C22 -1.0(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O4 . . 1_655 2.854(5) 0.77(4) 2.09(4) 174(4) no
N2 H2 O2 . . . 2.837(4) 0.94(5) 1.91(5) 172(4) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_mab004_1b_03a46N
_database_code_depnum_ccdc_archive 'CCDC 2087470'
loop_
_audit_author_name
_audit_author_address
'Misaki Okayasu'
;Toho University
Japan
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C25 H24 N3 O2 S'
_chemical_formula_moiety         'C25 H24 N3 O2 S'
_chemical_formula_weight         430.54
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   12.6908(4)
_cell_length_b                   11.0757(3)
_cell_length_c                   15.7411(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.683(3)
_cell_angle_gamma                90.0000
_cell_volume                     2211.61(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14531
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      29.56
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             908.00
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_T_max  0.995

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            34411
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.589
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5070
_reflns_number_gt                4399
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1177
_refine_ls_number_restraints     8
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         5070
_refine_ls_number_parameters     328
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0277P)²+1.8397P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.79102(4) 0.57659(5) 0.65167(4) 0.03016(17) Uani 0.910(2) 1 d . . P A 1
O1 O 0.76866(11) 0.65015(12) 0.72469(10) 0.0393(3) Uani 1 1 d . . . . .
O2 O 0.84651(11) 0.62815(13) 0.58221(10) 0.0373(4) Uani 0.910(2) 1 d . . P A 1
N1 N 0.68013(13) 0.52733(16) 0.60889(13) 0.0306(4) Uani 0.910(2) 1 d . . P A 1
H1 H 0.6875(19) 0.506(2) 0.5559(16) 0.037 Uiso 0.910(2) 1 d . U P A 1
N2 N 0.71880(14) 0.45403(16) 0.43218(12) 0.0422(4) Uani 1 1 d . . . . .
C5 C 0.51386(14) 0.39718(17) 0.78077(14) 0.0346(4) Uani 1 1 d . . . . .
C18 C 0.74617(14) 0.45405(16) 0.25572(13) 0.0314(4) Uani 1 1 d . . . . .
C6 C 0.59247(14) 0.46578(17) 0.74082(14) 0.0367(5) Uani 1 1 d . . . . .
H6 H 0.637129 0.515229 0.773256 0.044 Uiso 1 1 calc R U . . .
N3 N 0.77461(17) 0.4730(2) -0.01533(13) 0.0550(5) Uani 1 1 d . . . . .
C23 C 0.75713(14) 0.45912(17) 0.16249(13) 0.0328(4) Uani 1 1 d . . . . .
C22 C 0.78958(15) 0.56452(18) 0.12288(13) 0.0350(4) Uani 1 1 d . . . . .
H22 H 0.806883 0.632566 0.154979 0.042 Uiso 1 1 calc R U . . .
C4 C 0.44792(14) 0.32458(17) 0.73034(14) 0.0340(4) Uani 1 1 d . . . . .
H4 H 0.396348 0.278549 0.755850 0.041 Uiso 1 1 calc R U . . .
C17 C 0.81314(15) 0.51933(18) 0.31006(13) 0.0355(4) Uani 1 1 d . . . . .
H17 H 0.867993 0.564549 0.288461 0.043 Uiso 1 1 calc R U . . .
C19 C 0.66621(15) 0.38670(17) 0.29261(14) 0.0368(5) Uani 1 1 d . . . . .
H19 H 0.620693 0.339893 0.258967 0.044 Uiso 1 1 calc R U . . .
C2 C 0.53575(14) 0.38758(17) 0.60470(14) 0.0354(4) Uani 1 1 d . . . . .
H2 H 0.542842 0.384806 0.546099 0.043 Uiso 1 1 calc R U . . .
C3 C 0.45754(14) 0.31940(17) 0.64237(14) 0.0342(4) Uani 1 1 d . . . . .
C7 C 0.86162(14) 0.44732(18) 0.68832(16) 0.0416(5) Uani 1 1 d . . . . .
C20 C 0.65588(16) 0.39066(18) 0.37907(15) 0.0414(5) Uani 1 1 d . . . . .
H20 H 0.601539 0.346364 0.402313 0.050 Uiso 1 1 calc R U . . .
C1 C 0.60309(14) 0.45953(17) 0.65373(14) 0.0343(4) Uani 1 1 d . . . . .
C16 C 0.79731(16) 0.51624(19) 0.39628(14) 0.0403(5) Uani 1 1 d . . . . .
H16 H 0.843404 0.559539 0.431751 0.048 Uiso 1 1 calc R U . . .
C24 C 0.73379(16) 0.36034(19) 0.11032(15) 0.0424(5) Uani 1 1 d . . . . .
H24 H 0.711221 0.287939 0.133544 0.051 Uiso 1 1 calc R U . . .
C8 C 0.86275(16) 0.4189(2) 0.77396(17) 0.0477(6) Uani 1 1 d . . . . .
H8 H 0.827917 0.467636 0.812187 0.057 Uiso 1 1 calc R U . . .
C21 C 0.79584(18) 0.5671(2) 0.03562(14) 0.0449(5) Uani 1 1 d . . . . .
H21 H 0.816174 0.639138 0.010489 0.054 Uiso 1 1 calc R U . . .
C14 C 0.50102(16) 0.4050(2) 0.87431(14) 0.0367(5) Uani 0.916(3) 1 d . . P B 4
H14A H 0.569187 0.407555 0.902359 0.055 Uiso 0.916(3) 1 calc R U P B 4
H14B H 0.463087 0.335562 0.893387 0.055 Uiso 0.916(3) 1 calc R U P B 4
H14C H 0.462522 0.476857 0.887510 0.055 Uiso 0.916(3) 1 calc R U P B 4
C11 C 0.96683(16) 0.2716(2) 0.6591(2) 0.0551(7) Uani 1 1 d . . . . .
C10 C 0.96698(18) 0.2450(2) 0.7457(2) 0.0578(7) Uani 1 1 d . . . . .
H10 H 1.002487 0.176627 0.765342 0.069 Uiso 1 1 calc R U . . .
C12 C 0.91246(15) 0.37612(19) 0.63045(18) 0.0472(6) Uani 1 1 d . . . . .
H12 H 0.911018 0.396627 0.573134 0.057 Uiso 1 1 calc R U . . .
C13 C 0.38530(17) 0.24120(19) 0.58789(14) 0.0383(5) Uani 0.960(3) 1 d . . P C 3
H13A H 0.422475 0.170074 0.570960 0.057 Uiso 0.960(3) 1 calc R U P C 3
H13B H 0.362360 0.285496 0.538297 0.057 Uiso 0.960(3) 1 calc R U P C 3
H13C H 0.325149 0.218319 0.619787 0.057 Uiso 0.960(3) 1 calc R U P C 3
C25 C 0.74469(19) 0.3717(2) 0.02356(17) 0.0543(7) Uani 1 1 d . . . . .
H25 H 0.730251 0.304289 -0.010070 0.065 Uiso 1 1 calc R U . . .
C9 C 0.91690(18) 0.3160(2) 0.8022(2) 0.0567(7) Uani 1 1 d . . . . .
C15 C 1.0215(2) 0.1928(3) 0.6021(2) 0.0464(7) Uani 0.781(3) 1 d . . P D 5
H15A H 1.092205 0.179864 0.623471 0.070 Uiso 0.781(3) 1 calc R U P D 5
H15B H 1.023366 0.229439 0.546847 0.070 Uiso 0.781(3) 1 calc R U P D 5
H15C H 0.985267 0.116892 0.597951 0.070 Uiso 0.781(3) 1 calc R U P D 5
C26 C 0.9297(6) 0.2752(7) 0.8708(4) 0.0513(18) Uani 0.343(3) 1 d . . P E 6
H26A H 0.868164 0.230597 0.885946 0.077 Uiso 0.343(3) 1 calc R U P E 6
H26B H 0.941661 0.339500 0.910896 0.077 Uiso 0.343(3) 1 calc R U P E 6
H26C H 0.989678 0.222404 0.871625 0.077 Uiso 0.343(3) 1 calc R U P E 6
S1A S 0.7038(6) 0.5841(6) 0.6701(5) 0.053(2) Uani 0.090(2) 1 d . . P A 2
O2A O 0.6543(16) 0.653(2) 0.6033(13) 0.063(5) Uani 0.090(2) 1 d . . P A 2
N1A N 0.808(2) 0.502(2) 0.637(2) 0.080(9) Uani 0.090(2) 1 d . . P A 2
H1A H 0.822201 0.499996 0.584087 0.096 Uiso 0.090(2) 1 calc R U P A 2


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.4361(16) . ?
S1 O1 1.4439(16) . ?
S1 N1 1.6358(17) . ?
S1 C7 1.776(2) . ?
O1 S1A 1.382(8) . ?
N1 C1 1.435(3) . ?
N1 H1 0.87(3) . ?
N2 C20 1.338(3) . ?
N2 C16 1.349(3) . ?
C5 C4 1.392(3) . ?
C5 C6 1.416(3) . ?
C5 C14 1.489(3) . ?
C18 C17 1.391(3) . ?
C18 C19 1.399(3) . ?
C18 C23 1.479(3) . ?
C6 C1 1.383(3) . ?
C6 H6 0.9300 . ?
N3 C21 1.338(3) . ?
N3 C25 1.339(3) . ?
C23 C22 1.392(3) . ?
C23 C24 1.395(3) . ?
C22 C21 1.378(3) . ?
C22 H22 0.9300 . ?
C4 C3 1.395(3) . ?
C4 H4 0.9300 . ?
C17 C16 1.378(3) . ?
C17 H17 0.9300 . ?
C19 C20 1.372(3) . ?
C19 H19 0.9300 . ?
C2 C1 1.387(3) . ?
C2 C3 1.393(3) . ?
C2 H2 0.9300 . ?
C3 C13 1.510(3) . ?
C7 N1A 1.21(3) . ?
C7 C12 1.379(3) . ?
C7 C8 1.384(3) . ?
C20 H20 0.9300 . ?
C1 S1A 1.893(7) . ?
C16 H16 0.9300 . ?
C24 C25 1.382(4) . ?
C24 H24 0.9300 . ?
C8 C9 1.397(3) . ?
C8 H8 0.9300 . ?
C21 H21 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C11 C10 1.394(4) . ?
C11 C12 1.415(3) . ?
C11 C15 1.444(4) . ?
C10 C9 1.359(4) . ?
C10 H10 0.9300 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C25 H25 0.9300 . ?
C9 C26 1.177(7) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
S1A O2A 1.43(2) . ?
S1A N1A 1.70(2) . ?
N1A H1A 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.60(9) . . ?
O2 S1 N1 104.74(10) . . ?
O1 S1 N1 109.21(9) . . ?
O2 S1 C7 108.29(10) . . ?
O1 S1 C7 107.77(10) . . ?
N1 S1 C7 106.53(9) . . ?
C1 N1 S1 124.23(15) . . ?
C1 N1 H1 115.1(17) . . ?
S1 N1 H1 111.5(16) . . ?
C20 N2 C16 116.16(19) . . ?
C4 C5 C6 118.44(19) . . ?
C4 C5 C14 121.07(18) . . ?
C6 C5 C14 120.47(18) . . ?
C17 C18 C19 117.36(19) . . ?
C17 C18 C23 121.12(17) . . ?
C19 C18 C23 121.49(17) . . ?
C1 C6 C5 120.25(18) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C21 N3 C25 115.7(2) . . ?
C22 C23 C24 117.1(2) . . ?
C22 C23 C18 120.93(17) . . ?
C24 C23 C18 122.01(19) . . ?
C21 C22 C23 119.38(19) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C5 C4 C3 121.41(18) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C16 C17 C18 119.25(18) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C20 C19 C18 119.09(19) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C1 C2 C3 120.6(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 118.97(19) . . ?
C2 C3 C13 119.83(19) . . ?
C4 C3 C13 121.20(18) . . ?
N1A C7 C12 96.5(14) . . ?
N1A C7 C8 139.1(13) . . ?
C12 C7 C8 121.4(2) . . ?
C12 C7 S1 119.18(19) . . ?
C8 C7 S1 119.38(18) . . ?
N2 C20 C19 124.33(19) . . ?
N2 C20 H20 117.8 . . ?
C19 C20 H20 117.8 . . ?
C6 C1 C2 120.26(18) . . ?
C6 C1 N1 123.30(18) . . ?
C2 C1 N1 116.41(19) . . ?
C6 C1 S1A 85.0(3) . . ?
C2 C1 S1A 153.8(3) . . ?
N2 C16 C17 123.78(19) . . ?
N2 C16 H16 118.1 . . ?
C17 C16 H16 118.1 . . ?
C25 C24 C23 119.0(2) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C7 C8 C9 119.2(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
N3 C21 C22 124.4(2) . . ?
N3 C21 H21 117.8 . . ?
C22 C21 H21 117.8 . . ?
C5 C14 H14A 109.5 . . ?
C5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C11 C12 118.1(2) . . ?
C10 C11 C15 119.6(2) . . ?
C12 C11 C15 122.3(3) . . ?
C9 C10 C11 122.1(2) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C7 C12 C11 119.4(2) . . ?
C7 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C25 C24 124.5(2) . . ?
N3 C25 H25 117.8 . . ?
C24 C25 H25 117.8 . . ?
C26 C9 C10 109.0(4) . . ?
C26 C9 C8 131.2(5) . . ?
C10 C9 C8 119.9(3) . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C26 H26A 109.5 . . ?
C9 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C9 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O1 S1A O2A 114.5(10) . . ?
O1 S1A N1A 91.1(12) . . ?
O2A S1A N1A 112.9(16) . . ?
O1 S1A C1 149.1(5) . . ?
O2A S1A C1 90.5(10) . . ?
N1A S1A C1 95.6(10) . . ?
C7 N1A S1A 120(2) . . ?
C7 N1A H1A 120.1 . . ?
S1A N1A H1A 120.1 . . ?

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
O2 S1 N1 C1 174.55(16) . . . . ?
O1 S1 N1 C1 -56.22(18) . . . . ?
C7 S1 N1 C1 59.92(19) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C14 C5 C6 C1 -179.08(17) . . . . ?
C17 C18 C23 C22 -33.8(3) . . . . ?
C19 C18 C23 C22 144.10(18) . . . . ?
C17 C18 C23 C24 147.39(19) . . . . ?
C19 C18 C23 C24 -34.7(3) . . . . ?
C24 C23 C22 C21 0.8(3) . . . . ?
C18 C23 C22 C21 -178.03(18) . . . . ?
C6 C5 C4 C3 -0.5(3) . . . . ?
C14 C5 C4 C3 178.18(17) . . . . ?
C19 C18 C17 C16 -0.9(3) . . . . ?
C23 C18 C17 C16 177.18(18) . . . . ?
C17 C18 C19 C20 1.7(3) . . . . ?
C23 C18 C19 C20 -176.28(17) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C1 C2 C3 C13 -179.73(17) . . . . ?
C5 C4 C3 C2 0.7(3) . . . . ?
C5 C4 C3 C13 -179.55(17) . . . . ?
O2 S1 C7 C12 -35.15(18) . . . . ?
O1 S1 C7 C12 -165.86(15) . . . . ?
N1 S1 C7 C12 77.04(17) . . . . ?
O2 S1 C7 C8 146.10(16) . . . . ?
O1 S1 C7 C8 15.39(18) . . . . ?
N1 S1 C7 C8 -101.71(17) . . . . ?
C16 N2 C20 C19 -0.6(3) . . . . ?
C18 C19 C20 N2 -1.1(3) . . . . ?
C5 C6 C1 C2 1.1(3) . . . . ?
C5 C6 C1 N1 179.34(16) . . . . ?
C5 C6 C1 S1A 173.9(3) . . . . ?
C3 C2 C1 C6 -0.9(3) . . . . ?
C3 C2 C1 N1 -179.29(16) . . . . ?
C3 C2 C1 S1A -164.6(6) . . . . ?
S1 N1 C1 C6 25.1(3) . . . . ?
S1 N1 C1 C2 -156.56(15) . . . . ?
C20 N2 C16 C17 1.6(3) . . . . ?
C18 C17 C16 N2 -0.8(3) . . . . ?
C22 C23 C24 C25 0.5(3) . . . . ?
C18 C23 C24 C25 179.31(18) . . . . ?
N1A C7 C8 C9 155.5(19) . . . . ?
C12 C7 C8 C9 0.2(3) . . . . ?
S1 C7 C8 C9 178.92(16) . . . . ?
C25 N3 C21 C22 0.6(3) . . . . ?
C23 C22 C21 N3 -1.4(3) . . . . ?
C12 C11 C10 C9 0.1(3) . . . . ?
C15 C11 C10 C9 180.0(2) . . . . ?
N1A C7 C12 C11 -163.9(12) . . . . ?
C8 C7 C12 C11 0.1(3) . . . . ?
S1 C7 C12 C11 -178.61(15) . . . . ?
C10 C11 C12 C7 -0.2(3) . . . . ?
C15 C11 C12 C7 179.8(2) . . . . ?
C21 N3 C25 C24 0.8(3) . . . . ?
C23 C24 C25 N3 -1.4(3) . . . . ?
C11 C10 C9 C26 -179.2(4) . . . . ?
C11 C10 C9 C8 0.3(3) . . . . ?
C7 C8 C9 C26 178.9(5) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C6 C1 S1A O1 14.7(10) . . . . ?
C2 C1 S1A O1 -179.4(6) . . . . ?
C6 C1 S1A O2A -130.7(9) . . . . ?
C2 C1 S1A O2A 35.3(12) . . . . ?
C6 C1 S1A N1A 116.2(13) . . . . ?
C2 C1 S1A N1A -77.8(14) . . . . ?
C12 C7 N1A S1A 165.4(16) . . . . ?
C8 C7 N1A S1A 6(3) . . . . ?
O1 S1A N1A C7 57.0(19) . . . . ?
O2A S1A N1A C7 174.3(18) . . . . ?
C1 S1A N1A C7 -93(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N2 . . . 2.953(3) 0.87(3) 2.08(3) 175(2) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_sma_1d_s07a51N
_database_code_depnum_ccdc_archive 'CCDC 2087471'
loop_
_audit_author_name
_audit_author_address
'Misaki Okayasu'
;Toho University
Japan
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C26 H27 N3 O4 S'
_chemical_formula_moiety         'C26 H27 N3 O4 S'
_chemical_formula_weight         477.58
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.3499(5)
_cell_length_b                   11.4704(4)
_cell_length_c                   13.5710(6)
_cell_angle_alpha                101.723(4)
_cell_angle_beta                 95.458(4)
_cell_angle_gamma                110.537(4)
_cell_volume                     1172.00(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6832
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      29.55
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504.00
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.720
_exptl_absorpt_correction_T_max  0.993

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            37462
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_av_R_equivalents  0.0820
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.630
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5378
_reflns_number_gt                3797
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1370
_refine_ls_wR_factor_gt          0.1250
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         5378
_refine_ls_number_parameters     311
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0648P)²+0.3063P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.46
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.09101(7) 0.43468(5) 0.76093(4) 0.02545(16) Uani 1 1 d . . . . .
O1 O 0.06125(18) 0.30102(13) 0.72193(11) 0.0289(3) Uani 1 1 d . . . . .
O2 O -0.02508(18) 0.46754(14) 0.82216(11) 0.0301(4) Uani 1 1 d . . . . .
O3 O 0.2601(2) 1.00532(14) 0.65370(12) 0.0359(4) Uani 1 1 d . . . . .
O4 O 0.3249(2) 0.85068(15) 0.51004(12) 0.0385(4) Uani 1 1 d . . . . .
N1 N 0.0868(2) 0.48985(17) 0.65982(14) 0.0270(4) Uani 1 1 d . . . . .
N2 N 0.2082(2) 0.33208(17) 0.50801(13) 0.0309(4) Uani 1 1 d . . . . .
N3 N 0.3881(2) -0.08645(17) 0.10637(14) 0.0316(4) Uani 1 1 d . . . . .
C1 C 0.1306(3) 0.62333(19) 0.66387(16) 0.0256(5) Uani 1 1 d . . . . .
C2 C 0.0937(3) 0.7055(2) 0.73989(17) 0.0303(5) Uani 1 1 d . . . . .
H2 H 0.039582 0.674716 0.793038 0.036 Uiso 1 1 calc R U . . .
C3 C 0.1366(3) 0.8340(2) 0.73777(17) 0.0312(5) Uani 1 1 d . . . . .
H3 H 0.112495 0.890490 0.790464 0.037 Uiso 1 1 calc R U . . .
C4 C 0.2131(3) 0.8805(2) 0.66092(17) 0.0293(5) Uani 1 1 d . . . . .
C5 C 0.2486(3) 0.7963(2) 0.58269(16) 0.0285(5) Uani 1 1 d . . . . .
C6 C 0.2072(3) 0.6694(2) 0.58534(16) 0.0279(5) Uani 1 1 d . . . . .
H6 H 0.231325 0.612613 0.532852 0.033 Uiso 1 1 calc R U . . .
C7 C 0.3038(3) 0.51330(18) 0.83275(15) 0.0249(4) Uani 1 1 d . . . . .
C8 C 0.4358(3) 0.47831(19) 0.79723(16) 0.0270(5) Uani 1 1 d . . . . .
H8 H 0.410928 0.414040 0.735201 0.032 Uiso 1 1 calc R U . . .
C9 C 0.6030(3) 0.53778(19) 0.85289(16) 0.0282(5) Uani 1 1 d . . . . .
H9 H 0.693024 0.513912 0.828761 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6418(3) 0.63312(19) 0.94474(17) 0.0292(5) Uani 1 1 d . . . . .
C11 C 0.5082(3) 0.6671(2) 0.97772(16) 0.0299(5) Uani 1 1 d . . . . .
H11 H 0.533200 0.732638 1.038991 0.036 Uiso 1 1 calc R U . . .
C12 C 0.3394(3) 0.60792(19) 0.92347(16) 0.0283(5) Uani 1 1 d . . . . .
H12 H 0.249127 0.631430 0.947728 0.034 Uiso 1 1 calc R U . . .
C13 C 0.2417(3) 1.0935(2) 0.73837(19) 0.0389(6) Uani 1 1 d . . . . .
H13A H 0.278449 1.179421 0.725735 0.047 Uiso 1 1 calc R U . . .
H13B H 0.119766 1.065095 0.746734 0.047 Uiso 1 1 calc R U . . .
H13C H 0.314357 1.096683 0.800749 0.047 Uiso 1 1 calc R U . . .
C14 C 0.3685(3) 0.7713(2) 0.43055(17) 0.0357(5) Uani 1 1 d . . . . .
H14A H 0.422070 0.821880 0.383807 0.043 Uiso 1 1 calc R U . . .
H14B H 0.450501 0.738856 0.460504 0.043 Uiso 1 1 calc R U . . .
H14C H 0.262837 0.698678 0.392709 0.043 Uiso 1 1 calc R U . . .
C15 C 0.8260(3) 0.7011(2) 1.00257(18) 0.0356(5) Uani 1 1 d . . . . .
H15A H 0.894784 0.648696 0.980957 0.043 Uiso 1 1 calc R U . . .
H15B H 0.826256 0.710139 1.076705 0.043 Uiso 1 1 calc R U . . .
C16 C 0.9108(3) 0.8339(2) 0.9837(2) 0.0447(6) Uani 1 1 d . . . . .
H16A H 1.030117 0.875434 1.022326 0.054 Uiso 1 1 calc R U . . .
H16B H 0.912609 0.825131 0.910538 0.054 Uiso 1 1 calc R U . . .
H16C H 0.844131 0.886529 1.006217 0.054 Uiso 1 1 calc R U . . .
C17 C 0.2850(3) 0.3717(2) 0.43277(18) 0.0370(6) Uani 1 1 d . . . . .
H17 H 0.314357 0.459407 0.432157 0.044 Uiso 1 1 calc R U . . .
C18 C 0.3249(3) 0.2935(2) 0.35540(17) 0.0350(5) Uani 1 1 d . . . . .
H18 H 0.378498 0.327594 0.303304 0.042 Uiso 1 1 calc R U . . .
C19 C 0.2864(3) 0.16455(19) 0.35392(15) 0.0252(4) Uani 1 1 d . . . . .
C20 C 0.2087(3) 0.1229(2) 0.43347(16) 0.0283(5) Uani 1 1 d . . . . .
H20 H 0.181620 0.036556 0.437469 0.034 Uiso 1 1 calc R U . . .
C21 C 0.1709(3) 0.2080(2) 0.50678(16) 0.0305(5) Uani 1 1 d . . . . .
H21 H 0.115390 0.176565 0.559281 0.037 Uiso 1 1 calc R U . . .
C22 C 0.2920(3) -0.1318(2) 0.17370(17) 0.0332(5) Uani 1 1 d . . . . .
H22 H 0.244951 -0.222309 0.165203 0.040 Uiso 1 1 calc R U . . .
C23 C 0.2563(3) -0.0559(2) 0.25491(17) 0.0306(5) Uani 1 1 d . . . . .
H23 H 0.186781 -0.094220 0.300002 0.037 Uiso 1 1 calc R U . . .
C24 C 0.3236(3) 0.07815(19) 0.26996(15) 0.0247(4) Uani 1 1 d . . . . .
C25 C 0.4237(3) 0.1254(2) 0.20039(16) 0.0296(5) Uani 1 1 d . . . . .
H25 H 0.473108 0.215526 0.207013 0.036 Uiso 1 1 calc R U . . .
C26 C 0.4517(3) 0.0415(2) 0.12125(16) 0.0323(5) Uani 1 1 d . . . . .
H26 H 0.520309 0.077091 0.074722 0.039 Uiso 1 1 calc R U . . .
H1 H 0.128(3) 0.456(3) 0.616(2) 0.045(8) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.4334(15) . ?
S1 O1 1.4389(14) . ?
S1 N1 1.6259(19) . ?
S1 C7 1.764(2) . ?
O3 C4 1.373(2) . ?
O3 C13 1.427(3) . ?
O4 C5 1.363(3) . ?
O4 C14 1.426(3) . ?
N1 C1 1.432(3) . ?
N1 H1 0.81(3) . ?
N2 C17 1.330(3) . ?
N2 C21 1.342(3) . ?
N3 C22 1.338(3) . ?
N3 C26 1.338(3) . ?
C1 C2 1.385(3) . ?
C1 C6 1.395(3) . ?
C2 C3 1.397(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.411(3) . ?
C5 C6 1.382(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.393(3) . ?
C7 C12 1.394(3) . ?
C8 C9 1.381(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.405(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(3) . ?
C10 C15 1.507(3) . ?
C11 C12 1.385(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.524(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.383(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.395(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.393(3) . ?
C19 C24 1.484(3) . ?
C20 C21 1.386(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.384(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.402(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.387(3) . ?
C25 C26 1.386(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

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 118.85(9) . . ?
O2 S1 N1 109.38(9) . . ?
O1 S1 N1 104.67(9) . . ?
O2 S1 C7 107.94(9) . . ?
O1 S1 C7 108.20(9) . . ?
N1 S1 C7 107.27(10) . . ?
C4 O3 C13 115.90(18) . . ?
C5 O4 C14 117.76(17) . . ?
C1 N1 S1 123.53(15) . . ?
C1 N1 H1 111.8(19) . . ?
S1 N1 H1 111.5(19) . . ?
C17 N2 C21 116.01(19) . . ?
C22 N3 C26 115.71(18) . . ?
C2 C1 C6 119.61(19) . . ?
C2 C1 N1 122.52(19) . . ?
C6 C1 N1 117.82(18) . . ?
C1 C2 C3 119.4(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
O3 C4 C3 124.9(2) . . ?
O3 C4 C5 115.92(19) . . ?
C3 C4 C5 119.17(19) . . ?
O4 C5 C6 125.48(19) . . ?
O4 C5 C4 115.13(18) . . ?
C6 C5 C4 119.38(19) . . ?
C5 C6 C1 121.02(19) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C8 C7 C12 120.6(2) . . ?
C8 C7 S1 118.58(16) . . ?
C12 C7 S1 120.81(16) . . ?
C9 C8 C7 119.48(19) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.9(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 118.4(2) . . ?
C11 C10 C15 121.1(2) . . ?
C9 C10 C15 120.4(2) . . ?
C12 C11 C10 121.6(2) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C7 119.0(2) . . ?
C11 C12 H12 120.5 . . ?
C7 C12 H12 120.5 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 C16 111.54(18) . . ?
C10 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
C10 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C18 124.2(2) . . ?
N2 C17 H17 117.9 . . ?
C18 C17 H17 117.9 . . ?
C17 C18 C19 119.9(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 116.19(19) . . ?
C20 C19 C24 123.07(18) . . ?
C18 C19 C24 120.73(19) . . ?
C21 C20 C19 119.8(2) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
N2 C21 C20 123.9(2) . . ?
N2 C21 H21 118.0 . . ?
C20 C21 H21 118.0 . . ?
N3 C22 C23 124.5(2) . . ?
N3 C22 H22 117.7 . . ?
C23 C22 H22 117.7 . . ?
C22 C23 C24 119.4(2) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C25 C24 C23 116.24(19) . . ?
C25 C24 C19 121.77(18) . . ?
C23 C24 C19 121.98(19) . . ?
C26 C25 C24 120.16(19) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
N3 C26 C25 124.0(2) . . ?
N3 C26 H26 118.0 . . ?
C25 C26 H26 118.0 . . ?

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
O2 S1 N1 C1 59.05(19) . . . . ?
O1 S1 N1 C1 -172.58(16) . . . . ?
C7 S1 N1 C1 -57.78(19) . . . . ?
S1 N1 C1 C2 -34.5(3) . . . . ?
S1 N1 C1 C6 148.03(17) . . . . ?
C6 C1 C2 C3 -1.2(3) . . . . ?
N1 C1 C2 C3 -178.55(19) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C13 O3 C4 C3 6.2(3) . . . . ?
C13 O3 C4 C5 -173.48(18) . . . . ?
C2 C3 C4 O3 -179.60(19) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C14 O4 C5 C6 -0.9(3) . . . . ?
C14 O4 C5 C4 178.23(18) . . . . ?
O3 C4 C5 O4 -0.1(3) . . . . ?
C3 C4 C5 O4 -179.80(19) . . . . ?
O3 C4 C5 C6 179.13(18) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
O4 C5 C6 C1 179.3(2) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
N1 C1 C6 C5 178.18(18) . . . . ?
O2 S1 C7 C8 168.53(15) . . . . ?
O1 S1 C7 C8 38.72(18) . . . . ?
N1 S1 C7 C8 -73.70(17) . . . . ?
O2 S1 C7 C12 -11.1(2) . . . . ?
O1 S1 C7 C12 -140.89(17) . . . . ?
N1 S1 C7 C12 106.68(18) . . . . ?
C12 C7 C8 C9 0.3(3) . . . . ?
S1 C7 C8 C9 -179.34(15) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C8 C9 C10 C15 -177.50(18) . . . . ?
C9 C10 C11 C12 1.2(3) . . . . ?
C15 C10 C11 C12 178.02(19) . . . . ?
C10 C11 C12 C7 -1.0(3) . . . . ?
C8 C7 C12 C11 0.2(3) . . . . ?
S1 C7 C12 C11 179.86(15) . . . . ?
C11 C10 C15 C16 -75.7(3) . . . . ?
C9 C10 C15 C16 101.0(2) . . . . ?
C21 N2 C17 C18 0.8(3) . . . . ?
N2 C17 C18 C19 -0.9(4) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C17 C18 C19 C24 178.3(2) . . . . ?
C18 C19 C20 C21 1.4(3) . . . . ?
C24 C19 C20 C21 -177.14(19) . . . . ?
C17 N2 C21 C20 0.4(3) . . . . ?
C19 C20 C21 N2 -1.5(3) . . . . ?
C26 N3 C22 C23 0.0(3) . . . . ?
N3 C22 C23 C24 -0.1(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C22 C23 C24 C19 178.42(19) . . . . ?
C20 C19 C24 C25 -170.3(2) . . . . ?
C18 C19 C24 C25 11.3(3) . . . . ?
C20 C19 C24 C23 11.3(3) . . . . ?
C18 C19 C24 C23 -167.1(2) . . . . ?
C23 C24 C25 C26 0.3(3) . . . . ?
C19 C24 C25 C26 -178.22(19) . . . . ?
C22 N3 C26 C25 0.2(3) . . . . ?
C24 C25 C26 N3 -0.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N2 . . . 2.952(3) 0.81(3) 2.16(3) 169(3) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_akt004_2d_s03a15O
_database_code_depnum_ccdc_archive 'CCDC 2087467'
loop_
_audit_author_name
_audit_author_address
'Misaki Okayasu'
;Toho University
Japan
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C13 H12 F N O2 S'
_chemical_formula_moiety         'C13 H12 F N O2 S'
_chemical_formula_weight         265.30
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   9.1750(5)
_cell_length_b                   5.9502(3)
_cell_length_c                   22.5000(13)
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.764(5)
_cell_angle_gamma                90.0000
_cell_volume                     1222.13(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5861
_cell_measurement_theta_min      3.35
_cell_measurement_theta_max      29.45
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552.00
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.094
_exptl_absorpt_correction_T_max  0.989

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            18973
_diffrn_reflns_av_unetI/netI     0.0937
_diffrn_reflns_av_R_equivalents  0.1129
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         3.348
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2796
_reflns_number_gt                2185
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1440
_refine_ls_wR_factor_gt          0.1306
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2796
_refine_ls_number_parameters     173
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0497P)²+0.4747P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.53
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.40179(6) 0.82515(8) 0.30307(2) 0.01795(19) Uani 1 1 d . . . . .
F2 F 0.1793(11) 0.1947(11) 0.4937(3) 0.064(3) Uani 0.234(5) 1 d . . P A 2
F1 F 0.3915(2) 0.8556(3) 0.53980(8) 0.0403(7) Uani 0.766(5) 1 d . . P A 1
O1 O 0.39600(16) 1.0426(2) 0.32975(7) 0.0232(4) Uani 1 1 d . . . . .
O2 O 0.36080(18) 0.8012(2) 0.23988(7) 0.0234(4) Uani 1 1 d . . . . .
N1 N 0.2946(2) 0.6531(3) 0.33387(8) 0.0211(4) Uani 1 1 d . . . . .
H1 H 0.228391 0.581051 0.310053 0.025 Uiso 1 1 calc R U . . .
C1 C 0.2986(2) 0.6088(4) 0.39607(9) 0.0187(5) Uani 1 1 d . . . . .
C2 C 0.2423(3) 0.4044(4) 0.41330(10) 0.0253(5) Uani 1 1 d . . . . .
H2 H 0.207782 0.296490 0.384096 0.030 Uiso 1 1 calc R U . . .
C3 C 0.2370(3) 0.3601(4) 0.47333(12) 0.0354(6) Uani 1 1 d . . . . .
H3 H 0.196916 0.221514 0.484902 0.042 Uiso 0.766(5) 1 calc R U P A 1
C4 C 0.2885(3) 0.5116(4) 0.51697(11) 0.0329(6) Uani 1 1 d . . . . .
H4 H 0.285171 0.480217 0.558215 0.040 Uiso 1 1 calc R U . . .
C5 C 0.3443(3) 0.7080(4) 0.49807(11) 0.0302(6) Uani 1 1 d . . . . .
H5 H 0.381388 0.812873 0.527634 0.036 Uiso 0.234(5) 1 calc R U P A 2
C6 C 0.3507(3) 0.7655(4) 0.43901(10) 0.0260(5) Uani 1 1 d . . . . .
H6 H 0.389020 0.906161 0.428085 0.031 Uiso 1 1 calc R U . . .
C7 C 0.5825(2) 0.7221(3) 0.31833(9) 0.0158(4) Uani 1 1 d . . . . .
C8 C 0.6886(2) 0.8631(3) 0.34654(9) 0.0168(5) Uani 1 1 d . . . . .
H8 H 0.662024 1.006637 0.360478 0.020 Uiso 1 1 calc R U . . .
C9 C 0.8346(2) 0.7926(3) 0.35430(10) 0.0197(5) Uani 1 1 d . . . . .
C10 C 0.8682(3) 0.5800(4) 0.33338(10) 0.0218(5) Uani 1 1 d . . . . .
H10 H 0.967117 0.530277 0.337630 0.026 Uiso 1 1 calc R U . . .
C11 C 0.7602(3) 0.4397(3) 0.30648(10) 0.0223(5) Uani 1 1 d . . . . .
H11 H 0.785751 0.294650 0.293241 0.027 Uiso 1 1 calc R U . . .
C12 C 0.6156(2) 0.5089(3) 0.29876(9) 0.0204(5) Uani 1 1 d . . . . .
H12 H 0.541183 0.413125 0.280575 0.024 Uiso 1 1 calc R U . . .
C13 C 0.9520(3) 0.9435(4) 0.38417(12) 0.0307(6) Uani 1 1 d . . . . .
H13A H 0.907784 1.084807 0.395748 0.037 Uiso 1 1 calc R U . . .
H13B H 0.999474 0.868822 0.419814 0.037 Uiso 1 1 calc R U . . .
H13C H 1.025061 0.975104 0.356355 0.037 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.4297(16) . ?
S1 O2 1.4408(16) . ?
S1 N1 1.6227(19) . ?
S1 C7 1.769(2) . ?
F2 C3 1.228(7) . ?
F1 C5 1.326(3) . ?
N1 C1 1.421(3) . ?
N1 H1 0.8800 . ?
C1 C6 1.392(3) . ?
C1 C2 1.392(3) . ?
C2 C3 1.382(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.361(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.387(3) . ?
C7 C8 1.389(3) . ?
C8 C9 1.398(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(3) . ?
C9 C13 1.508(3) . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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 119.12(9) . . ?
O1 S1 N1 110.01(9) . . ?
O2 S1 N1 104.46(9) . . ?
O1 S1 C7 107.81(9) . . ?
O2 S1 C7 107.70(10) . . ?
N1 S1 C7 107.15(10) . . ?
C1 N1 S1 125.48(15) . . ?
C1 N1 H1 117.3 . . ?
S1 N1 H1 117.3 . . ?
C6 C1 C2 120.2(2) . . ?
C6 C1 N1 122.2(2) . . ?
C2 C1 N1 117.54(19) . . ?
C3 C2 C1 119.3(2) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
F2 C3 C4 112.8(4) . . ?
F2 C3 C2 125.2(4) . . ?
C4 C3 C2 121.8(2) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C5 C4 C3 116.8(2) . . ?
C5 C4 H4 121.6 . . ?
C3 C4 H4 121.6 . . ?
F1 C5 C4 117.0(2) . . ?
F1 C5 C6 118.4(2) . . ?
C4 C5 C6 124.6(2) . . ?
C4 C5 H5 117.7 . . ?
C6 C5 H5 117.7 . . ?
C5 C6 C1 117.3(2) . . ?
C5 C6 H6 121.4 . . ?
C1 C6 H6 121.4 . . ?
C12 C7 C8 122.1(2) . . ?
C12 C7 S1 119.11(16) . . ?
C8 C7 S1 118.64(16) . . ?
C7 C8 C9 119.62(19) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 118.1(2) . . ?
C10 C9 C13 121.2(2) . . ?
C8 C9 C13 120.63(19) . . ?
C11 C10 C9 121.4(2) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C12 C11 C10 120.6(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 118.1(2) . . ?
C11 C12 H12 121.0 . . ?
C7 C12 H12 121.0 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
O1 S1 N1 C1 -54.3(2) . . . . ?
O2 S1 N1 C1 176.71(17) . . . . ?
C7 S1 N1 C1 62.62(19) . . . . ?
S1 N1 C1 C6 26.6(3) . . . . ?
S1 N1 C1 C2 -156.09(17) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
N1 C1 C2 C3 -176.6(2) . . . . ?
C1 C2 C3 F2 173.8(6) . . . . ?
C1 C2 C3 C4 -1.1(4) . . . . ?
F2 C3 C4 C5 -175.1(6) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 F1 178.9(2) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
F1 C5 C6 C1 -179.2(2) . . . . ?
C4 C5 C6 C1 -1.2(4) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
N1 C1 C6 C5 177.5(2) . . . . ?
O1 S1 C7 C12 177.88(15) . . . . ?
O2 S1 C7 C12 -52.39(18) . . . . ?
N1 S1 C7 C12 59.50(18) . . . . ?
O1 S1 C7 C8 -5.83(19) . . . . ?
O2 S1 C7 C8 123.90(16) . . . . ?
N1 S1 C7 C8 -124.21(16) . . . . ?
C12 C7 C8 C9 1.8(3) . . . . ?
S1 C7 C8 C9 -174.36(16) . . . . ?
C7 C8 C9 C10 -0.3(3) . . . . ?
C7 C8 C9 C13 179.3(2) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C13 C9 C10 C11 179.3(2) . . . . ?
C9 C10 C11 C12 1.1(3) . . . . ?
C10 C11 C12 C7 0.4(3) . . . . ?
C8 C7 C12 C11 -1.8(3) . . . . ?
S1 C7 C12 C11 174.34(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O2 0.88 2.13 2.949(2) 155.3 2_545 yes
C6 H6 O1 0.95 2.36 3.024(3) 126.2 . yes

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_14s86a14_cd13
_database_code_depnum_ccdc_archive 'CCDC 2087478'
loop_
_audit_author_name
_audit_author_address
'Misaki Okayasu'
;Toho University
Japan
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H12 F N O2 S'
_chemical_formula_moiety         'C16 H12 F N O2 S'
_chemical_formula_weight         301.33
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 -1/2-X,-1/2+Y,+Z
7 +X,-1/2-Y,-1/2+Z
8 -1/2+X,+Y,-1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   11.5492(5)
_cell_length_b                   7.5883(4)
_cell_length_c                   31.0045(14)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     2717.2(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6330
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      29.16
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248.00
_exptl_absorpt_coefficient_mu    0.253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.749
_exptl_absorpt_correction_T_max  0.995

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            21952
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.628
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       39
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3091
_reflns_number_gt                2425
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0907
_refine_ls_wR_factor_gt          0.0853
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         3091
_refine_ls_number_parameters     194
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0382P)²+1.5331P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.40
_refine_diff_density_min         -0.42
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.62712(3) 0.40229(6) 0.40360(2) 0.01313(12) Uani 1 1 d . . . . .
F1 F 0.47306(9) -0.04161(15) 0.38102(3) 0.0246(3) Uani 1 1 d . . . . .
O1 O 0.73878(10) 0.40684(17) 0.38288(4) 0.0186(3) Uani 1 1 d . . . . .
O2 O 0.60271(10) 0.51964(17) 0.43865(4) 0.0187(3) Uani 1 1 d . . . . .
N1 N 0.61295(12) 0.2006(2) 0.42143(5) 0.0142(3) Uani 1 1 d . . . . .
C1 C 0.50522(14) 0.1469(2) 0.44017(5) 0.0130(3) Uani 1 1 d . . . . .
C2 C 0.46826(14) 0.2131(2) 0.47977(5) 0.0145(3) Uani 1 1 d . . . . .
H2 H 0.513884 0.297927 0.494584 0.017 Uiso 1 1 calc R U . . .
C3 C 0.36467(15) 0.1551(2) 0.49757(6) 0.0168(4) Uani 1 1 d . . . . .
H3 H 0.338892 0.202473 0.524257 0.020 Uiso 1 1 calc R U . . .
C4 C 0.29853(14) 0.0286(2) 0.47665(6) 0.0180(4) Uani 1 1 d . . . . .
H4 H 0.228307 -0.011397 0.489261 0.022 Uiso 1 1 calc R U . . .
C5 C 0.33475(15) -0.0400(2) 0.43730(6) 0.0172(4) Uani 1 1 d . . . . .
H5 H 0.290387 -0.127174 0.422806 0.021 Uiso 1 1 calc R U . . .
C6 C 0.43687(14) 0.0221(2) 0.41986(5) 0.0154(4) Uani 1 1 d . . . . .
C7 C 0.51891(13) 0.4379(2) 0.36407(5) 0.0129(3) Uani 1 1 d . . . . .
C8 C 0.53604(14) 0.3770(2) 0.32293(5) 0.0134(3) Uani 1 1 d . . . . .
H8 H 0.603057 0.309636 0.316335 0.016 Uiso 1 1 calc R U . . .
C9 C 0.45404(14) 0.4144(2) 0.29027(5) 0.0133(3) Uani 1 1 d . . . . .
C10 C 0.35178(14) 0.5103(2) 0.30132(5) 0.0152(4) Uani 1 1 d . . . . .
C11 C 0.33571(15) 0.5649(2) 0.34473(6) 0.0189(4) Uani 1 1 d . . . . .
H11 H 0.266826 0.625564 0.352488 0.023 Uiso 1 1 calc R U . . .
C12 C 0.41754(15) 0.5319(2) 0.37555(5) 0.0177(4) Uani 1 1 d . . . . .
H12 H 0.406537 0.571497 0.404322 0.021 Uiso 1 1 calc R U . . .
C13 C 0.27222(14) 0.5535(2) 0.26812(6) 0.0183(4) Uani 1 1 d . . . . .
H13 H 0.203245 0.615627 0.275034 0.022 Uiso 1 1 calc R U . . .
C14 C 0.29366(15) 0.5068(3) 0.22627(6) 0.0196(4) Uani 1 1 d . . . . .
H14 H 0.240493 0.539521 0.204306 0.024 Uiso 1 1 calc R U . . .
C15 C 0.39438(15) 0.4101(3) 0.21538(6) 0.0196(4) Uani 1 1 d . . . . .
H15 H 0.407851 0.376944 0.186268 0.024 Uiso 1 1 calc R U . . .
C16 C 0.47217(15) 0.3645(2) 0.24658(6) 0.0170(4) Uani 1 1 d . . . . .
H16 H 0.539143 0.298704 0.239033 0.020 Uiso 1 1 calc R U . . .
H1 H 0.6498(19) 0.129(3) 0.4059(7) 0.032(6) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.4330(12) . ?
S1 O1 1.4413(12) . ?
S1 N1 1.6355(15) . ?
S1 C7 1.7714(16) . ?
F1 C6 1.3634(19) . ?
N1 C1 1.432(2) . ?
N1 H1 0.84(2) . ?
C1 C6 1.384(2) . ?
C1 C2 1.394(2) . ?
C2 C3 1.389(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(2) . ?
C5 H5 0.9500 . ?
C7 C8 1.371(2) . ?
C7 C12 1.416(2) . ?
C8 C9 1.415(2) . ?
C8 H8 0.9500 . ?
C9 C16 1.422(2) . ?
C9 C10 1.429(2) . ?
C10 C13 1.418(2) . ?
C10 C11 1.420(2) . ?
C11 C12 1.367(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.368(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.416(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.365(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

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 119.95(7) . . ?
O2 S1 N1 107.79(8) . . ?
O1 S1 N1 105.22(8) . . ?
O2 S1 C7 106.92(8) . . ?
O1 S1 C7 108.61(7) . . ?
N1 S1 C7 107.83(7) . . ?
C1 N1 S1 119.35(12) . . ?
C1 N1 H1 119.3(16) . . ?
S1 N1 H1 111.1(16) . . ?
C6 C1 C2 118.22(15) . . ?
C6 C1 N1 120.35(15) . . ?
C2 C1 N1 121.39(15) . . ?
C3 C2 C1 119.96(16) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.51(16) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.20(16) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 118.24(16) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
F1 C6 C5 119.14(15) . . ?
F1 C6 C1 118.02(15) . . ?
C5 C6 C1 122.85(15) . . ?
C8 C7 C12 121.52(15) . . ?
C8 C7 S1 119.38(12) . . ?
C12 C7 S1 119.09(13) . . ?
C7 C8 C9 120.10(15) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C16 121.98(15) . . ?
C8 C9 C10 118.93(15) . . ?
C16 C9 C10 119.06(15) . . ?
C13 C10 C11 122.38(16) . . ?
C13 C10 C9 118.64(15) . . ?
C11 C10 C9 118.93(15) . . ?
C12 C11 C10 121.22(16) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C7 119.22(16) . . ?
C11 C12 H12 120.4 . . ?
C7 C12 H12 120.4 . . ?
C14 C13 C10 120.75(16) . . ?
C14 C13 H13 119.6 . . ?
C10 C13 H13 119.6 . . ?
C13 C14 C15 120.61(16) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 120.21(16) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C9 120.71(16) . . ?
C15 C16 H16 119.6 . . ?
C9 C16 H16 119.6 . . ?

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
O2 S1 N1 C1 57.04(14) . . . . ?
O1 S1 N1 C1 -173.86(12) . . . . ?
C7 S1 N1 C1 -58.08(14) . . . . ?
S1 N1 C1 C6 113.15(16) . . . . ?
S1 N1 C1 C2 -69.18(19) . . . . ?
C6 C1 C2 C3 -0.7(2) . . . . ?
N1 C1 C2 C3 -178.42(15) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 F1 -179.11(15) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C2 C1 C6 F1 179.66(14) . . . . ?
N1 C1 C6 F1 -2.6(2) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
N1 C1 C6 C5 177.20(15) . . . . ?
O2 S1 C7 C8 163.81(13) . . . . ?
O1 S1 C7 C8 33.04(16) . . . . ?
N1 S1 C7 C8 -80.50(15) . . . . ?
O2 S1 C7 C12 -14.98(16) . . . . ?
O1 S1 C7 C12 -145.75(14) . . . . ?
N1 S1 C7 C12 100.71(14) . . . . ?
C12 C7 C8 C9 2.9(2) . . . . ?
S1 C7 C8 C9 -175.83(12) . . . . ?
C7 C8 C9 C16 175.55(16) . . . . ?
C7 C8 C9 C10 -2.4(2) . . . . ?
C8 C9 C10 C13 177.49(15) . . . . ?
C16 C9 C10 C13 -0.5(2) . . . . ?
C8 C9 C10 C11 0.0(2) . . . . ?
C16 C9 C10 C11 -177.98(16) . . . . ?
C13 C10 C11 C12 -175.49(17) . . . . ?
C9 C10 C11 C12 1.9(3) . . . . ?
C10 C11 C12 C7 -1.4(3) . . . . ?
C8 C7 C12 C11 -1.0(3) . . . . ?
S1 C7 C12 C11 177.74(14) . . . . ?
C11 C10 C13 C14 176.44(17) . . . . ?
C9 C10 C13 C14 -1.0(3) . . . . ?
C10 C13 C14 C15 1.7(3) . . . . ?
C13 C14 C15 C16 -0.9(3) . . . . ?
C14 C15 C16 C9 -0.6(3) . . . . ?
C8 C9 C16 C15 -176.64(16) . . . . ?
C10 C9 C16 C15 1.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 F1 . . . 2.7491(18) 0.84(2) 2.54(2) 95.5(17) no
N1 H1 O1 . . 6_755 3.0544(19) 0.84(2) 2.24(2) 164(2) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_mfu355-s22a21N-block
_database_code_depnum_ccdc_archive 'CCDC 2087477'
loop_
_audit_author_name
_audit_author_address
'Misaki Okayasu'
;Toho University
Japan
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C54 H42 Br4 N8 O4 S2'
_chemical_formula_moiety         'C54 H42 Br4 N8 O4 S2'
_chemical_formula_weight         1250.71
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   11.7276(4)
_cell_length_b                   14.3853(4)
_cell_length_c                   16.9385(5)
_cell_angle_alpha                99.089(2)
_cell_angle_beta                 98.944(2)
_cell_angle_gamma                110.799(3)
_cell_volume                     2567.63(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    19669
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      27.02
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1252.00
_exptl_absorpt_coefficient_mu    3.281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.765
_exptl_absorpt_correction_T_max  0.877

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            81776
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.502
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             11753
_reflns_number_gt                8532
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.0779
_refine_ls_wR_factor_gt          0.0710
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         11753
_refine_ls_number_parameters     657
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0223P)²+1.5215P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.002
_refine_diff_density_max         0.72
_refine_diff_density_min         -0.74
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 1.19338(3) 0.86506(2) 0.32336(2) 0.02346(8) Uani 1 1 d . . . . .
Br2 Br 0.58281(3) 1.00858(2) 0.27441(2) 0.03275(9) Uani 1 1 d . . . . .
Br3 Br -0.15490(3) 0.59964(2) 1.15621(2) 0.02460(8) Uani 1 1 d . . . . .
Br4 Br 0.47138(3) 0.47383(2) 1.15727(2) 0.03367(9) Uani 1 1 d . . . . .
S1 S 0.70413(6) 0.64355(5) 0.38456(4) 0.01655(15) Uani 1 1 d . . . . .
S2 S 0.31838(6) 0.84525(5) 1.09369(4) 0.01818(15) Uani 1 1 d . . . . .
O1 O 0.60447(17) 0.57993(14) 0.41508(11) 0.0221(4) Uani 1 1 d . . . . .
O2 O 0.75108(17) 0.59760(14) 0.32242(11) 0.0202(4) Uani 1 1 d . . . . .
O3 O 0.41491(17) 0.91684(14) 1.06630(11) 0.0226(4) Uani 1 1 d . . . . .
O4 O 0.27092(17) 0.88047(14) 1.16045(11) 0.0228(4) Uani 1 1 d . . . . .
N1 N 0.8186(2) 0.70456(18) 0.46533(15) 0.0168(5) Uani 1 1 d . . . . .
N2 N 0.2028(2) 0.79071(17) 1.01252(15) 0.0175(5) Uani 1 1 d . . . . .
N3 N 0.7047(2) 0.74239(18) 0.59693(14) 0.0217(5) Uani 1 1 d . . . . .
N4 N 0.3158(2) 0.76517(17) 0.87537(14) 0.0203(5) Uani 1 1 d . . . . .
N5 N 1.0818(2) 0.9543(2) 0.74765(15) 0.0313(6) Uani 1 1 d . . . . .
N6 N 0.7192(2) 0.8489(2) 1.04828(17) 0.0356(7) Uani 1 1 d . . . . .
N7 N 0.6379(2) 0.2860(2) 0.50082(16) 0.0317(6) Uani 1 1 d . . . . .
N8 N 1.1292(2) 0.4874(2) 0.29605(16) 0.0314(6) Uani 1 1 d . . . . .
C1 C 0.9335(2) 0.78502(19) 0.46650(15) 0.0146(6) Uani 1 1 d . . . . .
C2 C 0.9942(2) 0.7852(2) 0.40179(16) 0.0164(6) Uani 1 1 d . . . . .
H2A H 0.957898 0.732650 0.352931 0.020 Uiso 1 1 calc R U . . .
C3 C 1.1093(2) 0.8645(2) 0.41083(16) 0.0170(6) Uani 1 1 d . . . . .
C4 C 1.1652(3) 0.9425(2) 0.48079(16) 0.0198(6) Uani 1 1 d . . . . .
H4 H 1.243815 0.995808 0.485201 0.024 Uiso 1 1 calc R U . . .
C5 C 1.1030(3) 0.9409(2) 0.54487(17) 0.0203(6) Uani 1 1 d . . . . .
H5 H 1.139591 0.993547 0.593670 0.024 Uiso 1 1 calc R U . . .
C6 C 0.9888(2) 0.8630(2) 0.53753(16) 0.0171(6) Uani 1 1 d . . . . .
H6 H 0.947321 0.862610 0.581463 0.021 Uiso 1 1 calc R U . . .
C7 C 0.6599(2) 0.7369(2) 0.34864(16) 0.0167(6) Uani 1 1 d . . . . .
C8 C 0.5901(2) 0.7788(2) 0.39120(17) 0.0196(6) Uani 1 1 d . . . . .
H8 H 0.560857 0.753152 0.435782 0.024 Uiso 1 1 calc R U . . .
C9 C 0.5644(3) 0.8580(2) 0.36744(17) 0.0221(6) Uani 1 1 d . . . . .
H9 H 0.516687 0.887420 0.395356 0.027 Uiso 1 1 calc R U . . .
C10 C 0.6088(3) 0.8943(2) 0.30242(17) 0.0211(6) Uani 1 1 d . . . . .
C11 C 0.6724(3) 0.8501(2) 0.25728(17) 0.0212(6) Uani 1 1 d . . . . .
H11 H 0.697280 0.873459 0.210836 0.025 Uiso 1 1 calc R U . . .
C12 C 0.6992(2) 0.7709(2) 0.28112(16) 0.0189(6) Uani 1 1 d . . . . .
H12 H 0.744071 0.739929 0.251601 0.023 Uiso 1 1 calc R U . . .
C13 C 0.0898(2) 0.7076(2) 1.00929(16) 0.0155(6) Uani 1 1 d . . . . .
C14 C 0.0313(3) 0.6371(2) 0.93407(17) 0.0196(6) Uani 1 1 d . . . . .
H14 H 0.069479 0.644543 0.888655 0.023 Uiso 1 1 calc R U . . .
C15 C -0.0809(3) 0.5569(2) 0.92507(17) 0.0227(7) Uani 1 1 d . . . . .
H15 H -0.120330 0.510164 0.873250 0.027 Uiso 1 1 calc R U . . .
C16 C -0.1370(3) 0.5436(2) 0.99112(17) 0.0229(7) Uani 1 1 d . . . . .
H16 H -0.213530 0.487378 0.985717 0.028 Uiso 1 1 calc R U . . .
C17 C -0.0782(2) 0.6147(2) 1.06509(16) 0.0179(6) Uani 1 1 d . . . . .
C18 C 0.0336(2) 0.6969(2) 1.07555(16) 0.0175(6) Uani 1 1 d . . . . .
H18 H 0.071155 0.745028 1.126853 0.021 Uiso 1 1 calc R U . . .
C19 C 0.3682(2) 0.7486(2) 1.11717(16) 0.0184(6) Uani 1 1 d . . . . .
C20 C 0.3329(3) 0.7018(2) 1.18054(16) 0.0210(6) Uani 1 1 d . . . . .
H20 H 0.286406 0.725108 1.214325 0.025 Uiso 1 1 calc R U . . .
C21 C 0.3657(3) 0.6214(2) 1.19401(17) 0.0227(7) Uani 1 1 d . . . . .
H21 H 0.342793 0.589269 1.237258 0.027 Uiso 1 1 calc R U . . .
C22 C 0.4326(3) 0.5884(2) 1.14334(18) 0.0226(6) Uani 1 1 d . . . . .
C23 C 0.4713(3) 0.6363(2) 1.08179(18) 0.0237(7) Uani 1 1 d . . . . .
H23 H 0.519658 0.613943 1.049125 0.028 Uiso 1 1 calc R U . . .
C24 C 0.4389(3) 0.7165(2) 1.06847(17) 0.0219(6) Uani 1 1 d . . . . .
H24 H 0.464559 0.749772 1.026319 0.026 Uiso 1 1 calc R U . . .
C25 C 0.7093(3) 0.8315(2) 0.63789(17) 0.0232(7) Uani 1 1 d . . . . .
H25 H 0.765329 0.892629 0.628052 0.028 Uiso 1 1 calc R U . . .
C26 C 0.6370(3) 0.8398(2) 0.69386(17) 0.0197(6) Uani 1 1 d . . . . .
H26 H 0.643414 0.905064 0.721107 0.024 Uiso 1 1 calc R U . . .
C27 C 0.5550(2) 0.7514(2) 0.70968(16) 0.0159(6) Uani 1 1 d . . . . .
C28 C 0.5499(3) 0.6586(2) 0.66701(16) 0.0191(6) Uani 1 1 d . . . . .
H28 H 0.495394 0.596198 0.675857 0.023 Uiso 1 1 calc R U . . .
C29 C 0.6246(3) 0.6580(2) 0.61170(17) 0.0212(6) Uani 1 1 d . . . . .
H29 H 0.618604 0.593749 0.582468 0.025 Uiso 1 1 calc R U . . .
C30 C 0.4229(3) 0.8441(2) 0.88079(17) 0.0207(6) Uani 1 1 d . . . . .
H30 H 0.444684 0.904536 0.921976 0.025 Uiso 1 1 calc R U . . .
C31 C 0.5034(2) 0.8422(2) 0.82944(16) 0.0177(6) Uani 1 1 d . . . . .
H31 H 0.578691 0.899986 0.836099 0.021 Uiso 1 1 calc R U . . .
C32 C 0.4736(2) 0.75529(19) 0.76810(15) 0.0135(6) Uani 1 1 d . . . . .
C33 C 0.3632(2) 0.6726(2) 0.76349(16) 0.0173(6) Uani 1 1 d . . . . .
H33 H 0.339828 0.610781 0.723593 0.021 Uiso 1 1 calc R U . . .
C34 C 0.2881(3) 0.6808(2) 0.81691(16) 0.0197(6) Uani 1 1 d . . . . .
H34 H 0.212789 0.623785 0.812115 0.024 Uiso 1 1 calc R U . . .
C35 C 1.0761(3) 0.8804(2) 0.78618(19) 0.0336(8) Uani 1 1 d . . . . .
H35 H 1.124350 0.841457 0.773873 0.040 Uiso 1 1 calc R U . . .
C36 C 1.0047(3) 0.8560(2) 0.84321(19) 0.0304(7) Uani 1 1 d . . . . .
H36 H 1.004167 0.801188 0.868188 0.037 Uiso 1 1 calc R U . . .
C37 C 0.9336(3) 0.9114(2) 0.86406(16) 0.0202(6) Uani 1 1 d . . . . .
C38 C 0.9391(3) 0.9898(2) 0.82391(18) 0.0282(7) Uani 1 1 d . . . . .
H38 H 0.892350 1.030437 0.835075 0.034 Uiso 1 1 calc R U . . .
C39 C 1.0134(3) 1.0078(3) 0.76770(19) 0.0342(8) Uani 1 1 d . . . . .
H39 H 1.016158 1.061905 0.741403 0.041 Uiso 1 1 calc R U . . .
C40 C 0.7566(3) 0.7805(3) 1.0094(2) 0.0458(10) Uani 1 1 d . . . . .
H40 H 0.735715 0.716600 1.024436 0.055 Uiso 1 1 calc R U . . .
C41 C 0.8232(3) 0.7956(3) 0.9491(2) 0.0367(8) Uani 1 1 d . . . . .
H41 H 0.845258 0.742938 0.923212 0.044 Uiso 1 1 calc R U . . .
C42 C 0.8577(3) 0.8891(2) 0.92659(17) 0.0217(6) Uani 1 1 d . . . . .
C43 C 0.8190(3) 0.9603(2) 0.96634(17) 0.0261(7) Uani 1 1 d . . . . .
H43 H 0.839465 1.025276 0.953284 0.031 Uiso 1 1 calc R U . . .
C44 C 0.7501(3) 0.9367(3) 1.02532(19) 0.0310(7) Uani 1 1 d . . . . .
H44 H 0.723475 0.986599 1.050752 0.037 Uiso 1 1 calc R U . . .
C45 C 0.6901(3) 0.3861(2) 0.50287(18) 0.0308(7) Uani 1 1 d . . . . .
H45 H 0.658017 0.430057 0.531350 0.037 Uiso 1 1 calc R U . . .
C46 C 0.7874(3) 0.4296(2) 0.46630(17) 0.0258(7) Uani 1 1 d . . . . .
H46 H 0.820463 0.501205 0.470201 0.031 Uiso 1 1 calc R U . . .
C47 C 0.8365(3) 0.3677(2) 0.42381(17) 0.0216(6) Uani 1 1 d . . . . .
C48 C 0.7828(3) 0.2635(2) 0.42141(18) 0.0267(7) Uani 1 1 d . . . . .
H48 H 0.812853 0.217582 0.393470 0.032 Uiso 1 1 calc R U . . .
C49 C 0.6859(3) 0.2275(3) 0.45984(19) 0.0331(8) Uani 1 1 d . . . . .
H49 H 0.650915 0.156195 0.456934 0.040 Uiso 1 1 calc R U . . .
C50 C 1.0606(3) 0.5390(2) 0.3197(2) 0.0326(8) Uani 1 1 d . . . . .
H50 H 1.077751 0.604131 0.307483 0.039 Uiso 1 1 calc R U . . .
C51 C 0.9667(3) 0.5038(2) 0.36059(19) 0.0286(7) Uani 1 1 d . . . . .
H51 H 0.920501 0.543963 0.374639 0.034 Uiso 1 1 calc R U . . .
C52 C 0.9395(3) 0.4100(2) 0.38126(17) 0.0225(6) Uani 1 1 d . . . . .
C53 C 1.0119(3) 0.3558(2) 0.35789(18) 0.0250(7) Uani 1 1 d . . . . .
H53 H 0.998486 0.291332 0.370718 0.030 Uiso 1 1 calc R U . . .
C54 C 1.1032(3) 0.3969(2) 0.31595(18) 0.0303(7) Uani 1 1 d . . . . .
H54 H 1.150333 0.358221 0.300300 0.036 Uiso 1 1 calc R U . . .
H1 H 0.791(3) 0.714(2) 0.5012(18) 0.013(8) Uiso 1 1 d . . . . .
H2 H 0.233(3) 0.783(2) 0.974(2) 0.033(10) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C3 1.903(3) . ?
Br2 C10 1.892(3) . ?
Br3 C17 1.907(3) . ?
Br4 C22 1.898(3) . ?
S1 O1 1.4312(19) . ?
S1 O2 1.4376(19) . ?
S1 N1 1.630(2) . ?
S1 C7 1.760(3) . ?
S2 O3 1.4295(19) . ?
S2 O4 1.4354(19) . ?
S2 N2 1.633(2) . ?
S2 C19 1.763(3) . ?
N1 C1 1.426(3) . ?
N1 H1 0.75(3) . ?
N2 C13 1.421(3) . ?
N2 H2 0.80(3) . ?
N3 C29 1.334(4) . ?
N3 C25 1.336(4) . ?
N4 C30 1.339(3) . ?
N4 C34 1.341(3) . ?
N5 C35 1.320(4) . ?
N5 C39 1.338(4) . ?
N6 C44 1.323(4) . ?
N6 C40 1.337(4) . ?
N7 C49 1.334(4) . ?
N7 C45 1.342(4) . ?
N8 C50 1.337(4) . ?
N8 C54 1.338(4) . ?
C1 C6 1.393(4) . ?
C1 C2 1.397(4) . ?
C2 C3 1.390(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.382(4) . ?
C4 C5 1.397(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.393(4) . ?
C7 C8 1.396(4) . ?
C8 C9 1.380(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(4) . ?
C11 C12 1.386(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.389(4) . ?
C13 C14 1.396(4) . ?
C14 C15 1.375(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.382(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.395(4) . ?
C19 C24 1.395(4) . ?
C20 C21 1.382(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.385(4) . ?
C23 C24 1.376(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.385(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.391(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.389(4) . ?
C27 C32 1.486(4) . ?
C28 C29 1.380(4) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 C31 1.384(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.389(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.393(4) . ?
C33 C34 1.377(4) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 C36 1.381(4) . ?
C35 H35 0.9500 . ?
C36 C37 1.389(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.395(4) . ?
C37 C42 1.488(4) . ?
C38 C39 1.382(4) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 C41 1.377(5) . ?
C40 H40 0.9500 . ?
C41 C42 1.394(4) . ?
C41 H41 0.9500 . ?
C42 C43 1.385(4) . ?
C43 C44 1.389(4) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
C45 C46 1.383(4) . ?
C45 H45 0.9500 . ?
C46 C47 1.390(4) . ?
C46 H46 0.9500 . ?
C47 C48 1.396(4) . ?
C47 C52 1.495(4) . ?
C48 C49 1.379(4) . ?
C48 H48 0.9500 . ?
C49 H49 0.9500 . ?
C50 C51 1.379(4) . ?
C50 H50 0.9500 . ?
C51 C52 1.387(4) . ?
C51 H51 0.9500 . ?
C52 C53 1.401(4) . ?
C53 C54 1.385(4) . ?
C53 H53 0.9500 . ?
C54 H54 0.9500 . ?

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 119.46(11) . . ?
O1 S1 N1 104.85(12) . . ?
O2 S1 N1 108.55(12) . . ?
O1 S1 C7 108.89(12) . . ?
O2 S1 C7 108.19(12) . . ?
N1 S1 C7 106.14(12) . . ?
O3 S2 O4 119.77(11) . . ?
O3 S2 N2 104.48(12) . . ?
O4 S2 N2 108.37(12) . . ?
O3 S2 C19 108.60(12) . . ?
O4 S2 C19 108.69(12) . . ?
N2 S2 C19 106.10(12) . . ?
C1 N1 S1 125.12(19) . . ?
C1 N1 H1 114(2) . . ?
S1 N1 H1 108(2) . . ?
C13 N2 S2 124.17(19) . . ?
C13 N2 H2 114(2) . . ?
S2 N2 H2 107(2) . . ?
C29 N3 C25 116.7(2) . . ?
C30 N4 C34 116.9(2) . . ?
C35 N5 C39 115.6(3) . . ?
C44 N6 C40 115.6(3) . . ?
C49 N7 C45 115.5(3) . . ?
C50 N8 C54 115.6(3) . . ?
C6 C1 C2 119.8(2) . . ?
C6 C1 N1 117.4(2) . . ?
C2 C1 N1 122.7(2) . . ?
C3 C2 C1 118.2(2) . . ?
C3 C2 H2A 120.9 . . ?
C1 C2 H2A 120.9 . . ?
C4 C3 C2 122.7(2) . . ?
C4 C3 Br1 118.7(2) . . ?
C2 C3 Br1 118.55(19) . . ?
C3 C4 C5 118.3(3) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.8(2) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C12 C7 C8 121.2(3) . . ?
C12 C7 S1 120.0(2) . . ?
C8 C7 S1 118.7(2) . . ?
C9 C8 C7 118.9(3) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 119.4(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 122.2(3) . . ?
C11 C10 Br2 118.5(2) . . ?
C9 C10 Br2 119.4(2) . . ?
C10 C11 C12 118.6(3) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C11 C12 C7 119.6(3) . . ?
C11 C12 H12 120.2 . . ?
C7 C12 H12 120.2 . . ?
C18 C13 C14 119.6(2) . . ?
C18 C13 N2 123.2(2) . . ?
C14 C13 N2 117.2(2) . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 118.0(3) . . ?
C17 C16 H16 121.0 . . ?
C15 C16 H16 121.0 . . ?
C18 C17 C16 122.7(2) . . ?
C18 C17 Br3 118.5(2) . . ?
C16 C17 Br3 118.8(2) . . ?
C17 C18 C13 118.5(2) . . ?
C17 C18 H18 120.8 . . ?
C13 C18 H18 120.8 . . ?
C20 C19 C24 120.5(3) . . ?
C20 C19 S2 120.9(2) . . ?
C24 C19 S2 118.6(2) . . ?
C21 C20 C19 119.8(3) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 118.9(3) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
C23 C22 C21 121.8(3) . . ?
C23 C22 Br4 118.6(2) . . ?
C21 C22 Br4 119.6(2) . . ?
C24 C23 C22 119.3(3) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C19 119.7(3) . . ?
C23 C24 H24 120.2 . . ?
C19 C24 H24 120.2 . . ?
N3 C25 C26 123.7(3) . . ?
N3 C25 H25 118.2 . . ?
C26 C25 H25 118.2 . . ?
C25 C26 C27 119.2(3) . . ?
C25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
C28 C27 C26 117.2(2) . . ?
C28 C27 C32 121.1(2) . . ?
C26 C27 C32 121.7(2) . . ?
C29 C28 C27 119.5(2) . . ?
C29 C28 H28 120.3 . . ?
C27 C28 H28 120.3 . . ?
N3 C29 C28 123.7(3) . . ?
N3 C29 H29 118.1 . . ?
C28 C29 H29 118.1 . . ?
N4 C30 C31 123.3(2) . . ?
N4 C30 H30 118.3 . . ?
C31 C30 H30 118.3 . . ?
C30 C31 C32 119.7(2) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C31 C32 C33 116.8(2) . . ?
C31 C32 C27 121.5(2) . . ?
C33 C32 C27 121.7(2) . . ?
C34 C33 C32 119.8(2) . . ?
C34 C33 H33 120.1 . . ?
C32 C33 H33 120.1 . . ?
N4 C34 C33 123.4(3) . . ?
N4 C34 H34 118.3 . . ?
C33 C34 H34 118.3 . . ?
N5 C35 C36 124.4(3) . . ?
N5 C35 H35 117.8 . . ?
C36 C35 H35 117.8 . . ?
C35 C36 C37 120.1(3) . . ?
C35 C36 H36 120.0 . . ?
C37 C36 H36 120.0 . . ?
C36 C37 C38 116.1(3) . . ?
C36 C37 C42 121.8(3) . . ?
C38 C37 C42 122.1(3) . . ?
C39 C38 C37 119.2(3) . . ?
C39 C38 H38 120.4 . . ?
C37 C38 H38 120.4 . . ?
N5 C39 C38 124.7(3) . . ?
N5 C39 H39 117.7 . . ?
C38 C39 H39 117.7 . . ?
N6 C40 C41 124.9(3) . . ?
N6 C40 H40 117.5 . . ?
C41 C40 H40 117.5 . . ?
C40 C41 C42 119.2(3) . . ?
C40 C41 H41 120.4 . . ?
C42 C41 H41 120.4 . . ?
C43 C42 C41 116.3(3) . . ?
C43 C42 C37 122.0(3) . . ?
C41 C42 C37 121.7(3) . . ?
C42 C43 C44 119.9(3) . . ?
C42 C43 H43 120.0 . . ?
C44 C43 H43 120.0 . . ?
N6 C44 C43 124.1(3) . . ?
N6 C44 H44 118.0 . . ?
C43 C44 H44 118.0 . . ?
N7 C45 C46 124.4(3) . . ?
N7 C45 H45 117.8 . . ?
C46 C45 H45 117.8 . . ?
C45 C46 C47 119.5(3) . . ?
C45 C46 H46 120.3 . . ?
C47 C46 H46 120.3 . . ?
C46 C47 C48 116.5(3) . . ?
C46 C47 C52 121.9(3) . . ?
C48 C47 C52 121.6(3) . . ?
C49 C48 C47 119.6(3) . . ?
C49 C48 H48 120.2 . . ?
C47 C48 H48 120.2 . . ?
N7 C49 C48 124.5(3) . . ?
N7 C49 H49 117.7 . . ?
C48 C49 H49 117.7 . . ?
N8 C50 C51 124.3(3) . . ?
N8 C50 H50 117.8 . . ?
C51 C50 H50 117.8 . . ?
C50 C51 C52 120.2(3) . . ?
C50 C51 H51 119.9 . . ?
C52 C51 H51 119.9 . . ?
C51 C52 C53 116.1(3) . . ?
C51 C52 C47 122.0(3) . . ?
C53 C52 C47 121.9(3) . . ?
C54 C53 C52 119.5(3) . . ?
C54 C53 H53 120.2 . . ?
C52 C53 H53 120.2 . . ?
N8 C54 C53 124.3(3) . . ?
N8 C54 H54 117.9 . . ?
C53 C54 H54 117.9 . . ?

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
O1 S1 N1 C1 -172.9(2) . . . . ?
O2 S1 N1 C1 58.3(2) . . . . ?
C7 S1 N1 C1 -57.8(2) . . . . ?
O3 S2 N2 C13 174.5(2) . . . . ?
O4 S2 N2 C13 -56.7(2) . . . . ?
C19 S2 N2 C13 59.9(2) . . . . ?
S1 N1 C1 C6 145.8(2) . . . . ?
S1 N1 C1 C2 -37.6(4) . . . . ?
C6 C1 C2 C3 0.0(4) . . . . ?
N1 C1 C2 C3 -176.6(2) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C1 C2 C3 Br1 179.57(19) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
Br1 C3 C4 C5 -179.5(2) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C1 0.0(4) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
N1 C1 C6 C5 176.8(2) . . . . ?
O1 S1 C7 C12 -145.9(2) . . . . ?
O2 S1 C7 C12 -14.6(2) . . . . ?
N1 S1 C7 C12 101.7(2) . . . . ?
O1 S1 C7 C8 36.9(2) . . . . ?
O2 S1 C7 C8 168.2(2) . . . . ?
N1 S1 C7 C8 -75.5(2) . . . . ?
C12 C7 C8 C9 -2.6(4) . . . . ?
S1 C7 C8 C9 174.6(2) . . . . ?
C7 C8 C9 C10 -0.3(4) . . . . ?
C8 C9 C10 C11 3.7(4) . . . . ?
C8 C9 C10 Br2 -175.9(2) . . . . ?
C9 C10 C11 C12 -4.0(4) . . . . ?
Br2 C10 C11 C12 175.6(2) . . . . ?
C10 C11 C12 C7 1.0(4) . . . . ?
C8 C7 C12 C11 2.2(4) . . . . ?
S1 C7 C12 C11 -174.9(2) . . . . ?
S2 N2 C13 C18 35.3(4) . . . . ?
S2 N2 C13 C14 -147.8(2) . . . . ?
C18 C13 C14 C15 -0.3(4) . . . . ?
N2 C13 C14 C15 -177.4(2) . . . . ?
C13 C14 C15 C16 -1.1(4) . . . . ?
C14 C15 C16 C17 1.6(4) . . . . ?
C15 C16 C17 C18 -0.6(4) . . . . ?
C15 C16 C17 Br3 178.9(2) . . . . ?
C16 C17 C18 C13 -0.9(4) . . . . ?
Br3 C17 C18 C13 179.68(19) . . . . ?
C14 C13 C18 C17 1.3(4) . . . . ?
N2 C13 C18 C17 178.2(2) . . . . ?
O3 S2 C19 C20 146.6(2) . . . . ?
O4 S2 C19 C20 14.8(3) . . . . ?
N2 S2 C19 C20 -101.6(2) . . . . ?
O3 S2 C19 C24 -36.4(2) . . . . ?
O4 S2 C19 C24 -168.2(2) . . . . ?
N2 S2 C19 C24 75.4(2) . . . . ?
C24 C19 C20 C21 -1.5(4) . . . . ?
S2 C19 C20 C21 175.4(2) . . . . ?
C19 C20 C21 C22 -0.5(4) . . . . ?
C20 C21 C22 C23 2.5(4) . . . . ?
C20 C21 C22 Br4 -176.9(2) . . . . ?
C21 C22 C23 C24 -2.3(4) . . . . ?
Br4 C22 C23 C24 177.0(2) . . . . ?
C22 C23 C24 C19 0.2(4) . . . . ?
C20 C19 C24 C23 1.6(4) . . . . ?
S2 C19 C24 C23 -175.4(2) . . . . ?
C29 N3 C25 C26 0.4(4) . . . . ?
N3 C25 C26 C27 0.4(4) . . . . ?
C25 C26 C27 C28 -0.5(4) . . . . ?
C25 C26 C27 C32 -179.0(3) . . . . ?
C26 C27 C28 C29 -0.2(4) . . . . ?
C32 C27 C28 C29 178.4(2) . . . . ?
C25 N3 C29 C28 -1.2(4) . . . . ?
C27 C28 C29 N3 1.1(4) . . . . ?
C34 N4 C30 C31 0.4(4) . . . . ?
N4 C30 C31 C32 0.6(4) . . . . ?
C30 C31 C32 C33 -1.6(4) . . . . ?
C30 C31 C32 C27 177.7(2) . . . . ?
C28 C27 C32 C31 159.0(3) . . . . ?
C26 C27 C32 C31 -22.6(4) . . . . ?
C28 C27 C32 C33 -21.8(4) . . . . ?
C26 C27 C32 C33 156.6(3) . . . . ?
C31 C32 C33 C34 1.7(4) . . . . ?
C27 C32 C33 C34 -177.6(2) . . . . ?
C30 N4 C34 C33 -0.3(4) . . . . ?
C32 C33 C34 N4 -0.8(4) . . . . ?
C39 N5 C35 C36 0.7(5) . . . . ?
N5 C35 C36 C37 -0.7(5) . . . . ?
C35 C36 C37 C38 0.5(4) . . . . ?
C35 C36 C37 C42 -178.5(3) . . . . ?
C36 C37 C38 C39 -0.4(4) . . . . ?
C42 C37 C38 C39 178.7(3) . . . . ?
C35 N5 C39 C38 -0.6(5) . . . . ?
C37 C38 C39 N5 0.4(5) . . . . ?
C44 N6 C40 C41 0.1(5) . . . . ?
N6 C40 C41 C42 1.3(6) . . . . ?
C40 C41 C42 C43 -1.4(5) . . . . ?
C40 C41 C42 C37 177.8(3) . . . . ?
C36 C37 C42 C43 159.5(3) . . . . ?
C38 C37 C42 C43 -19.5(4) . . . . ?
C36 C37 C42 C41 -19.7(4) . . . . ?
C38 C37 C42 C41 161.3(3) . . . . ?
C41 C42 C43 C44 0.3(4) . . . . ?
C37 C42 C43 C44 -178.9(3) . . . . ?
C40 N6 C44 C43 -1.4(5) . . . . ?
C42 C43 C44 N6 1.2(5) . . . . ?
C49 N7 C45 C46 -0.2(4) . . . . ?
N7 C45 C46 C47 0.3(5) . . . . ?
C45 C46 C47 C48 -0.3(4) . . . . ?
C45 C46 C47 C52 178.4(3) . . . . ?
C46 C47 C48 C49 0.3(4) . . . . ?
C52 C47 C48 C49 -178.4(3) . . . . ?
C45 N7 C49 C48 0.3(5) . . . . ?
C47 C48 C49 N7 -0.3(5) . . . . ?
C54 N8 C50 C51 -1.2(5) . . . . ?
N8 C50 C51 C52 1.2(5) . . . . ?
C50 C51 C52 C53 -0.2(4) . . . . ?
C50 C51 C52 C47 -178.5(3) . . . . ?
C46 C47 C52 C51 -19.4(4) . . . . ?
C48 C47 C52 C51 159.2(3) . . . . ?
C46 C47 C52 C53 162.4(3) . . . . ?
C48 C47 C52 C53 -19.0(4) . . . . ?
C51 C52 C53 C54 -0.6(4) . . . . ?
C47 C52 C53 C54 177.7(3) . . . . ?
C50 N8 C54 C53 0.2(4) . . . . ?
C52 C53 C54 N8 0.7(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N3 . . . 2.848(4) 0.75(3) 2.10(3) 176(3) no
N2 H2 N4 . . . 2.885(4) 0.80(4) 2.08(4) 178(3) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_16s22a21_ab31v2
_database_code_depnum_ccdc_archive 'CCDC 2087476'
loop_
_audit_author_name
_audit_author_address
'Misaki Okayasu'
;Toho University
Japan
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C12 H9 Br2 N O2 S'
_chemical_formula_moiety         'C12 H9 Br2 N O2 S'
_chemical_formula_weight         391.08
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
_space_group_IT_number           33
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,1/2+Z
3 1/2-X,1/2+Y,1/2+Z
4 1/2+X,1/2-Y,+Z
#------------------------------------------------------------------------------
_cell_length_a                   9.9580(4)
_cell_length_b                   21.7896(10)
_cell_length_c                   6.0999(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1323.56(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5617
_cell_measurement_theta_min      3.45
_cell_measurement_theta_max      29.67
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.962
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760.00
_exptl_absorpt_coefficient_mu    6.292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.409
_exptl_absorpt_correction_T_max  0.686

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            10151
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.771
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.948
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2824
_reflns_number_gt                2590
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_max     0.856
_reflns_Friedel_fraction_full    0.889

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0541
_refine_ls_wR_factor_gt          0.0525
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         2824
_refine_ls_number_parameters     167
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0165P)²+0.0807P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 998 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(8)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 1.14037(4) 0.64460(2) 0.73508(8) 0.02195(12) Uani 1 1 d . . . . .
Br2 Br 0.28483(4) 0.78218(2) 0.11018(9) 0.02362(13) Uani 1 1 d . . . . .
S1 S 0.56976(9) 0.57928(4) 0.70757(16) 0.0108(2) Uani 1 1 d . . . . .
O1 O 0.6384(3) 0.60818(13) 0.8853(5) 0.0154(7) Uani 1 1 d . . . . .
O2 O 0.4598(2) 0.53811(12) 0.7541(5) 0.0168(6) Uani 1 1 d . . . . .
N1 N 0.6749(3) 0.53723(15) 0.5693(6) 0.0123(7) Uani 1 1 d . . . . .
C1 C 0.8035(4) 0.55729(18) 0.4929(7) 0.0119(9) Uani 1 1 d . . . . .
C2 C 0.8409(4) 0.54021(18) 0.2816(7) 0.0133(9) Uani 1 1 d . . . . .
H2 H 0.779645 0.519189 0.188856 0.016 Uiso 1 1 calc R U . . .
C3 C 0.9694(4) 0.55440(18) 0.2086(8) 0.0174(9) Uani 1 1 d . . . . .
H3 H 0.995852 0.542513 0.065143 0.021 Uiso 1 1 calc R U . . .
C4 C 1.0596(4) 0.58545(19) 0.3404(8) 0.0185(10) Uani 1 1 d . . . . .
H4 H 1.147239 0.594998 0.289322 0.022 Uiso 1 1 calc R U . . .
C5 C 1.0187(4) 0.60226(19) 0.5489(7) 0.0136(9) Uani 1 1 d . . . . .
C6 C 0.8920(4) 0.58870(17) 0.6292(8) 0.0131(8) Uani 1 1 d . . . . .
H6 H 0.866317 0.600506 0.773090 0.016 Uiso 1 1 calc R U . . .
C7 C 0.5054(4) 0.63680(17) 0.5325(7) 0.0114(9) Uani 1 1 d . . . . .
C8 C 0.4927(4) 0.69648(17) 0.6108(8) 0.0159(8) Uani 1 1 d . . . . .
H8 H 0.528619 0.707582 0.749524 0.019 Uiso 1 1 calc R U . . .
C9 C 0.4267(4) 0.7395(2) 0.4823(8) 0.0186(9) Uani 1 1 d . . . . .
H9 H 0.415065 0.780299 0.533571 0.022 Uiso 1 1 calc R U . . .
C10 C 0.3779(4) 0.72242(19) 0.2795(7) 0.0153(10) Uani 1 1 d . . . . .
C11 C 0.3936(4) 0.66384(19) 0.1996(7) 0.0156(9) Uani 1 1 d . . . . .
H11 H 0.361104 0.653354 0.058001 0.019 Uiso 1 1 calc R U . . .
C12 C 0.4572(4) 0.62035(19) 0.3283(7) 0.0134(9) Uani 1 1 d . . . . .
H12 H 0.467753 0.579501 0.276600 0.016 Uiso 1 1 calc R U . . .
H1 H 0.637(4) 0.509(2) 0.486(8) 0.012(11) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C5 1.900(4) . ?
Br2 C10 1.903(4) . ?
S1 O1 1.428(3) . ?
S1 O2 1.444(3) . ?
S1 N1 1.627(3) . ?
S1 C7 1.767(4) . ?
N1 C1 1.431(5) . ?
N1 H1 0.88(5) . ?
C1 C6 1.392(6) . ?
C1 C2 1.392(6) . ?
C2 C3 1.390(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(6) . ?
C6 H6 0.9500 . ?
C7 C12 1.382(6) . ?
C7 C8 1.391(5) . ?
C8 C9 1.387(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.380(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.375(6) . ?
C11 C12 1.384(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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 119.20(18) . . ?
O1 S1 N1 109.49(17) . . ?
O2 S1 N1 103.90(17) . . ?
O1 S1 C7 108.64(18) . . ?
O2 S1 C7 106.53(18) . . ?
N1 S1 C7 108.63(18) . . ?
C1 N1 S1 124.9(3) . . ?
C1 N1 H1 114(3) . . ?
S1 N1 H1 115(3) . . ?
C6 C1 C2 121.0(4) . . ?
C6 C1 N1 121.5(4) . . ?
C2 C1 N1 117.4(4) . . ?
C3 C2 C1 118.9(4) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 121.4(4) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 118.2(4) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C4 C5 C6 122.4(4) . . ?
C4 C5 Br1 119.4(3) . . ?
C6 C5 Br1 118.2(3) . . ?
C5 C6 C1 118.1(4) . . ?
C5 C6 H6 121.0 . . ?
C1 C6 H6 121.0 . . ?
C12 C7 C8 121.4(4) . . ?
C12 C7 S1 119.1(3) . . ?
C8 C7 S1 119.2(3) . . ?
C9 C8 C7 118.7(4) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C10 C9 C8 119.4(4) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C11 C10 C9 121.8(4) . . ?
C11 C10 Br2 119.9(3) . . ?
C9 C10 Br2 118.3(3) . . ?
C10 C11 C12 119.1(4) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C7 C12 C11 119.5(4) . . ?
C7 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?

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
O1 S1 N1 C1 -49.0(4) . . . . ?
O2 S1 N1 C1 -177.4(3) . . . . ?
C7 S1 N1 C1 69.5(4) . . . . ?
S1 N1 C1 C6 46.8(5) . . . . ?
S1 N1 C1 C2 -137.8(3) . . . . ?
C6 C1 C2 C3 0.7(6) . . . . ?
N1 C1 C2 C3 -174.6(3) . . . . ?
C1 C2 C3 C4 -0.6(6) . . . . ?
C2 C3 C4 C5 0.0(6) . . . . ?
C3 C4 C5 C6 0.5(6) . . . . ?
C3 C4 C5 Br1 179.7(3) . . . . ?
C4 C5 C6 C1 -0.3(6) . . . . ?
Br1 C5 C6 C1 -179.5(3) . . . . ?
C2 C1 C6 C5 -0.3(6) . . . . ?
N1 C1 C6 C5 174.9(4) . . . . ?
O1 S1 C7 C12 167.8(3) . . . . ?
O2 S1 C7 C12 -62.6(4) . . . . ?
N1 S1 C7 C12 48.8(4) . . . . ?
O1 S1 C7 C8 -18.2(4) . . . . ?
O2 S1 C7 C8 111.4(3) . . . . ?
N1 S1 C7 C8 -137.2(3) . . . . ?
C12 C7 C8 C9 1.9(6) . . . . ?
S1 C7 C8 C9 -171.9(3) . . . . ?
C7 C8 C9 C10 -1.3(6) . . . . ?
C8 C9 C10 C11 -0.4(6) . . . . ?
C8 C9 C10 Br2 178.8(3) . . . . ?
C9 C10 C11 C12 1.5(6) . . . . ?
Br2 C10 C11 C12 -177.7(3) . . . . ?
C8 C7 C12 C11 -0.8(6) . . . . ?
S1 C7 C12 C11 173.1(3) . . . . ?
C10 C11 C12 C7 -0.9(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O2 . . 2_664 2.862(4) 0.88(5) 2.00(5) 167(4) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_17s97a01_ab49
_database_code_depnum_ccdc_archive 'CCDC 2087480'
loop_
_audit_author_name
_audit_author_address
'Misaki Okayasu'
;Toho University
Japan
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C13 H10 F3 N O2 S'
_chemical_formula_moiety         'C13 H10 F3 N O2 S'
_chemical_formula_weight         301.28
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.0813(4)
_cell_length_b                   20.4639(13)
_cell_length_c                   12.2504(9)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.757(6)
_cell_angle_gamma                90.0000
_cell_volume                     1273.72(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8476
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      29.56
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616.00
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.290
_exptl_absorpt_correction_T_max  0.957

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            20381
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_av_R_equivalents  0.1046
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.594
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2930
_reflns_number_gt                2450
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0676
_refine_ls_wR_factor_ref         0.1812
_refine_ls_wR_factor_gt          0.1769
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         2930
_refine_ls_number_parameters     185
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0762P)²+2.7963P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.83
_refine_diff_density_min         -0.47
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.39909(15) 0.77882(3) 0.33225(6) 0.0165(2) Uani 1 1 d . . . . .
F1 F 0.8943(5) 0.56922(11) 0.6883(2) 0.0483(7) Uani 1 1 d . . . . .
F2 F 0.7400(6) 0.50009(10) 0.57630(19) 0.0498(7) Uani 1 1 d . . . . .
F3 F 0.4967(6) 0.53944(15) 0.6997(3) 0.0681(10) Uani 1 1 d . . . . .
O1 O 0.4863(5) 0.76326(11) 0.22481(17) 0.0226(5) Uani 1 1 d . . . . .
O2 O 0.1310(4) 0.79716(11) 0.34970(18) 0.0220(5) Uani 1 1 d . . . . .
N1 N 0.5853(5) 0.83872(12) 0.3756(2) 0.0176(5) Uani 1 1 d . . . . .
H1 H 0.745(8) 0.8306(16) 0.367(3) 0.015(8) Uiso 1 1 d . . . . .
C1 C 0.5273(6) 0.87037(14) 0.4781(2) 0.0178(6) Uani 1 1 d . . . . .
C2 C 0.3227(7) 0.91512(16) 0.4823(3) 0.0253(7) Uani 1 1 d . . . . .
H2 H 0.217963 0.923813 0.419170 0.030 Uiso 1 1 calc R U . . .
C3 C 0.2729(8) 0.94699(16) 0.5796(3) 0.0296(8) Uani 1 1 d . . . . .
H3 H 0.131438 0.977219 0.583475 0.036 Uiso 1 1 calc R U . . .
C4 C 0.4282(7) 0.93505(16) 0.6714(3) 0.0265(7) Uani 1 1 d . . . . .
H4 H 0.393963 0.957411 0.737689 0.032 Uiso 1 1 calc R U . . .
C5 C 0.6320(7) 0.89078(18) 0.6666(3) 0.0298(8) Uani 1 1 d . . . . .
H5 H 0.739159 0.882879 0.729378 0.036 Uiso 1 1 calc R U . . .
C6 C 0.6810(7) 0.85759(17) 0.5695(3) 0.0262(7) Uani 1 1 d . . . . .
H6 H 0.819157 0.826398 0.566303 0.031 Uiso 1 1 calc R U . . .
C7 C 0.4717(6) 0.71131(14) 0.4180(2) 0.0155(6) Uani 1 1 d . . . . .
C8 C 0.6711(6) 0.66881(15) 0.3876(2) 0.0209(6) Uani 1 1 d . . . . .
H8 H 0.760078 0.674770 0.320623 0.025 Uiso 1 1 calc R U . . .
C9 C 0.7379(6) 0.61756(15) 0.4567(3) 0.0228(7) Uani 1 1 d . . . . .
H9 H 0.873390 0.587921 0.437319 0.027 Uiso 1 1 calc R U . . .
C10 C 0.6053(6) 0.60980(14) 0.5544(2) 0.0198(6) Uani 1 1 d . . . . .
C11 C 0.4070(7) 0.65259(15) 0.5844(3) 0.0223(7) Uani 1 1 d . . . . .
H11 H 0.317794 0.646639 0.651324 0.027 Uiso 1 1 calc R U . . .
C12 C 0.3398(7) 0.70416(15) 0.5158(2) 0.0209(6) Uani 1 1 d . . . . .
H12 H 0.205685 0.734094 0.535516 0.025 Uiso 1 1 calc R U . . .
C13 C 0.6835(7) 0.55487(15) 0.6293(3) 0.0247(7) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.430(2) . ?
S1 O2 1.432(2) . ?
S1 N1 1.633(3) . ?
S1 C7 1.772(3) . ?
F1 C13 1.317(4) . ?
F2 C13 1.329(4) . ?
F3 C13 1.328(4) . ?
N1 C1 1.446(4) . ?
N1 H1 0.84(4) . ?
C1 C6 1.382(4) . ?
C1 C2 1.387(4) . ?
C2 C3 1.385(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.395(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.388(4) . ?
C7 C8 1.390(4) . ?
C8 C9 1.387(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.391(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(4) . ?
C10 C13 1.502(4) . ?
C11 C12 1.389(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?

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 120.18(13) . . ?
O1 S1 N1 106.35(14) . . ?
O2 S1 N1 107.62(14) . . ?
O1 S1 C7 107.92(14) . . ?
O2 S1 C7 107.87(14) . . ?
N1 S1 C7 106.08(13) . . ?
C1 N1 S1 119.7(2) . . ?
C1 N1 H1 114(2) . . ?
S1 N1 H1 111(2) . . ?
C6 C1 C2 120.7(3) . . ?
C6 C1 N1 120.0(3) . . ?
C2 C1 N1 119.3(3) . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 120.4(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 119.6(3) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C12 C7 C8 121.8(3) . . ?
C12 C7 S1 119.7(2) . . ?
C8 C7 S1 118.4(2) . . ?
C9 C8 C7 118.9(3) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 C13 119.9(3) . . ?
C9 C10 C13 119.0(3) . . ?
C10 C11 C12 119.5(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C7 C12 C11 119.0(3) . . ?
C7 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
F1 C13 F3 106.3(3) . . ?
F1 C13 F2 106.1(3) . . ?
F3 C13 F2 106.1(3) . . ?
F1 C13 C10 112.0(3) . . ?
F3 C13 C10 112.9(3) . . ?
F2 C13 C10 112.9(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
O1 S1 N1 C1 173.4(2) . . . . ?
O2 S1 N1 C1 43.4(3) . . . . ?
C7 S1 N1 C1 -71.9(3) . . . . ?
S1 N1 C1 C6 104.9(3) . . . . ?
S1 N1 C1 C2 -77.4(3) . . . . ?
C6 C1 C2 C3 -0.2(5) . . . . ?
N1 C1 C2 C3 -177.9(3) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C2 C1 C6 C5 -0.9(5) . . . . ?
N1 C1 C6 C5 176.8(3) . . . . ?
C4 C5 C6 C1 1.3(5) . . . . ?
O1 S1 C7 C12 -160.1(2) . . . . ?
O2 S1 C7 C12 -28.8(3) . . . . ?
N1 S1 C7 C12 86.2(3) . . . . ?
O1 S1 C7 C8 23.4(3) . . . . ?
O2 S1 C7 C8 154.6(2) . . . . ?
N1 S1 C7 C8 -90.3(3) . . . . ?
C12 C7 C8 C9 0.6(5) . . . . ?
S1 C7 C8 C9 177.0(2) . . . . ?
C7 C8 C9 C10 -0.1(5) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C8 C9 C10 C13 -178.8(3) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
C13 C10 C11 C12 178.5(3) . . . . ?
C8 C7 C12 C11 -0.8(5) . . . . ?
S1 C7 C12 C11 -177.2(2) . . . . ?
C10 C11 C12 C7 0.6(5) . . . . ?
C11 C10 C13 F1 -98.3(4) . . . . ?
C9 C10 C13 F1 80.4(4) . . . . ?
C11 C10 C13 F3 21.7(5) . . . . ?
C9 C10 C13 F3 -159.6(3) . . . . ?
C11 C10 C13 F2 142.0(3) . . . . ?
C9 C10 C13 F2 -39.3(4) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_yho002-2_1d_s16a06N
_database_code_depnum_ccdc_archive 'CCDC 2087472'
loop_
_audit_author_name
_audit_author_address
'Misaki Okayasu'
;Toho University
Japan
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C24 H22 F N3 O2 S'
_chemical_formula_moiety         'C24 H22 F N3 O2 S'
_chemical_formula_weight         435.52
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   10.0096(3)
_cell_length_b                   12.4631(6)
_cell_length_c                   17.7972(7)
_cell_angle_alpha                80.489(4)
_cell_angle_beta                 73.938(3)
_cell_angle_gamma                87.660(3)
_cell_volume                     2104.19(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19495
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      29.62
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912.00
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_T_max  0.991

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            67401
_diffrn_reflns_av_unetI/netI     0.0953
_diffrn_reflns_av_R_equivalents  0.1223
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.585
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             9635
_reflns_number_gt                7272
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0951
_refine_ls_wR_factor_ref         0.2847
_refine_ls_wR_factor_gt          0.2732
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         9635
_refine_ls_number_parameters     563
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1236P)²+9.9761P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.75
_refine_diff_density_min         -0.74
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 1.08680(11) 0.50010(8) 0.28074(6) 0.0198(3) Uani 1 1 d . . . . .
S2 S 0.40140(10) 0.99945(8) 0.70151(6) 0.0169(2) Uani 1 1 d . . . . .
F1 F 1.5024(3) 0.8177(2) 0.07919(16) 0.0285(6) Uani 1 1 d . . . . .
F2 F 0.6556(3) 0.7032(2) 0.91345(16) 0.0286(6) Uani 1 1 d . . . . .
O1 O 1.0985(3) 0.4041(2) 0.2445(2) 0.0252(7) Uani 1 1 d . . . . .
O2 O 1.0992(3) 0.4914(3) 0.35990(19) 0.0270(7) Uani 1 1 d . . . . .
O3 O 0.3753(3) 1.1008(2) 0.73079(19) 0.0218(7) Uani 1 1 d . . . . .
O4 O 0.4827(3) 0.9986(3) 0.62120(17) 0.0230(7) Uani 1 1 d . . . . .
N1 N 0.9352(4) 0.5554(3) 0.2847(2) 0.0201(8) Uani 1 1 d . . . . .
N2 N 0.2551(4) 0.9426(3) 0.7072(2) 0.0191(7) Uani 1 1 d . . . . .
H2 H 0.242347 0.923940 0.664041 0.023 Uiso 1 1 calc R U . . .
N3 N 0.8924(4) 0.7030(3) 0.4036(2) 0.0240(8) Uani 1 1 d . . . . .
N4 N 0.8256(4) 1.0533(3) 0.6910(2) 0.0280(9) Uani 1 1 d . . . . .
N5 N 0.3081(4) 0.7847(3) 0.6008(2) 0.0226(8) Uani 1 1 d . . . . .
N6 N 0.4749(4) 0.4364(3) 0.3085(2) 0.0251(8) Uani 1 1 d . . . . .
C1 C 0.8861(4) 0.5870(3) 0.2163(2) 0.0175(8) Uani 1 1 d . . . . .
C2 C 0.8291(5) 0.6910(3) 0.2056(2) 0.0199(9) Uani 1 1 d . . . . .
H2A H 0.827740 0.739244 0.241881 0.024 Uiso 1 1 calc R U . . .
C3 C 0.7749(5) 0.7232(4) 0.1419(3) 0.0246(9) Uani 1 1 d . . . . .
H3 H 0.735823 0.793628 0.134841 0.030 Uiso 1 1 calc R U . . .
C4 C 0.7770(5) 0.6538(4) 0.0882(3) 0.0216(9) Uani 1 1 d . . . . .
H4 H 0.740296 0.677220 0.044422 0.026 Uiso 1 1 calc R U . . .
C5 C 0.8330(4) 0.5498(3) 0.0983(2) 0.0196(9) Uani 1 1 d . . . . .
C6 C 0.8869(4) 0.5165(4) 0.1630(2) 0.0193(8) Uani 1 1 d . . . . .
H6 H 0.924181 0.445511 0.170684 0.023 Uiso 1 1 calc R U . . .
C7 C 1.2116(4) 0.5958(3) 0.2179(2) 0.0177(8) Uani 1 1 d . . . . .
C8 C 1.3007(5) 0.5693(4) 0.1484(3) 0.0222(9) Uani 1 1 d . . . . .
H8 H 1.293448 0.500640 0.133212 0.027 Uiso 1 1 calc R U . . .
C9 C 1.4003(5) 0.6446(4) 0.1015(3) 0.0225(9) Uani 1 1 d . . . . .
H9 H 1.463438 0.628256 0.054167 0.027 Uiso 1 1 calc R U . . .
C10 C 1.4051(5) 0.7438(4) 0.1254(3) 0.0215(9) Uani 1 1 d . . . . .
C11 C 1.3168(5) 0.7725(4) 0.1933(3) 0.0238(9) Uani 1 1 d . . . . .
H11 H 1.323352 0.841902 0.207565 0.029 Uiso 1 1 calc R U . . .
C12 C 1.2178(5) 0.6966(4) 0.2405(3) 0.0222(9) Uani 1 1 d . . . . .
H12 H 1.154949 0.713476 0.287793 0.027 Uiso 1 1 calc R U . . .
C13 C 0.8253(5) 0.4696(4) 0.0447(3) 0.0254(10) Uani 1 1 d . . . . .
H13A H 0.909618 0.423827 0.037156 0.030 Uiso 1 1 calc R U . . .
H13B H 0.823199 0.509867 -0.007851 0.030 Uiso 1 1 calc R U . . .
C14 C 0.6971(5) 0.3970(4) 0.0784(3) 0.0316(11) Uani 1 1 d . . . . .
H14A H 0.695714 0.346205 0.042097 0.038 Uiso 1 1 calc R U . . .
H14B H 0.699715 0.356015 0.129979 0.038 Uiso 1 1 calc R U . . .
H14C H 0.613338 0.442014 0.084994 0.038 Uiso 1 1 calc R U . . .
C15 C 0.1461(4) 0.9217(3) 0.7792(2) 0.0173(8) Uani 1 1 d . . . . .
C16 C 0.0968(5) 0.8149(4) 0.8077(3) 0.0228(9) Uani 1 1 d . . . . .
H16 H 0.140469 0.756591 0.781937 0.027 Uiso 1 1 calc R U . . .
C17 C -0.0166(5) 0.7956(4) 0.8739(3) 0.0258(10) Uani 1 1 d . . . . .
H17 H -0.052826 0.723878 0.892718 0.031 Uiso 1 1 calc R U . . .
C18 C -0.0776(5) 0.8806(4) 0.9131(3) 0.0234(9) Uani 1 1 d . . . . .
H18 H -0.154197 0.865960 0.958869 0.028 Uiso 1 1 calc R U . . .
C19 C -0.0284(4) 0.9864(4) 0.8864(3) 0.0204(9) Uani 1 1 d . . . . .
C20 C 0.0835(4) 1.0057(4) 0.8185(2) 0.0187(8) Uani 1 1 d . . . . .
H20 H 0.117599 1.077861 0.798892 0.022 Uiso 1 1 calc R U . . .
C21 C 0.4799(4) 0.9127(3) 0.7656(2) 0.0168(8) Uani 1 1 d . . . . .
C22 C 0.4993(4) 0.9459(4) 0.8324(3) 0.0205(9) Uani 1 1 d . . . . .
H22 H 0.471324 1.016582 0.843829 0.025 Uiso 1 1 calc R U . . .
C23 C 0.5600(5) 0.8754(4) 0.8828(3) 0.0226(9) Uani 1 1 d . . . . .
H23 H 0.573884 0.896580 0.928940 0.027 Uiso 1 1 calc R U . . .
C24 C 0.5990(5) 0.7742(4) 0.8634(3) 0.0226(9) Uani 1 1 d . . . . .
C25 C 0.5812(5) 0.7384(3) 0.7976(3) 0.0210(9) Uani 1 1 d . . . . .
H25 H 0.609644 0.667581 0.786659 0.025 Uiso 1 1 calc R U . . .
C26 C 0.5203(4) 0.8089(4) 0.7477(2) 0.0196(9) Uani 1 1 d . . . . .
H26 H 0.506247 0.786966 0.701810 0.024 Uiso 1 1 calc R U . . .
C27 C -0.0888(5) 1.0824(4) 0.9266(3) 0.0238(9) Uani 1 1 d . . . . .
H27A H -0.105849 1.141451 0.885743 0.029 Uiso 1 1 calc R U . . .
H27B H -0.018064 1.109233 0.948462 0.029 Uiso 1 1 calc R U . . .
C28 C -0.2229(5) 1.0613(4) 0.9928(3) 0.0301(11) Uani 1 1 d . . . . .
H28A H -0.252548 1.128398 1.014494 0.036 Uiso 1 1 calc R U . . .
H28B H -0.295298 1.037046 0.971832 0.036 Uiso 1 1 calc R U . . .
H28C H -0.207238 1.004727 1.034747 0.036 Uiso 1 1 calc R U . . .
C29 C 0.8212(5) 0.7966(4) 0.4010(3) 0.0280(10) Uani 1 1 d . . . . .
H29 H 0.780528 0.816714 0.358450 0.034 Uiso 1 1 calc R U . . .
C30 C 0.8035(5) 0.8655(4) 0.4565(3) 0.0273(10) Uani 1 1 d . . . . .
H30 H 0.750498 0.930085 0.452093 0.033 Uiso 1 1 calc R U . . .
C31 C 0.8641(4) 0.8392(4) 0.5191(2) 0.0201(9) Uani 1 1 d . . . . .
C32 C 0.9374(5) 0.7420(4) 0.5224(3) 0.0221(9) Uani 1 1 d . . . . .
H32 H 0.979235 0.719712 0.564227 0.027 Uiso 1 1 calc R U . . .
C33 C 0.9490(5) 0.6781(4) 0.4646(3) 0.0251(10) Uani 1 1 d . . . . .
H33 H 1.000157 0.612390 0.468103 0.030 Uiso 1 1 calc R U . . .
C34 C 0.8123(5) 1.0888(4) 0.6179(3) 0.0278(10) Uani 1 1 d . . . . .
H34 H 0.793236 1.163708 0.604537 0.033 Uiso 1 1 calc R U . . .
C35 C 0.8246(5) 1.0233(4) 0.5611(3) 0.0245(9) Uani 1 1 d . . . . .
H35 H 0.814435 1.053281 0.510364 0.029 Uiso 1 1 calc R U . . .
C36 C 0.8521(4) 0.9128(4) 0.5786(2) 0.0194(9) Uani 1 1 d . . . . .
C37 C 0.8673(4) 0.8744(4) 0.6544(3) 0.0230(9) Uani 1 1 d . . . . .
H37 H 0.886761 0.799897 0.669180 0.028 Uiso 1 1 calc R U . . .
C38 C 0.8535(5) 0.9466(4) 0.7072(3) 0.0254(10) Uani 1 1 d . . . . .
H38 H 0.864316 0.919264 0.758236 0.030 Uiso 1 1 calc R U . . .
C39 C 0.4026(5) 0.8131(4) 0.5314(3) 0.0233(9) Uani 1 1 d . . . . .
H39 H 0.449647 0.880672 0.522436 0.028 Uiso 1 1 calc R U . . .
C40 C 0.4360(5) 0.7502(4) 0.4718(3) 0.0217(9) Uani 1 1 d . . . . .
H40 H 0.503459 0.775250 0.423375 0.026 Uiso 1 1 calc R U . . .
C41 C 0.3711(4) 0.6503(3) 0.4828(2) 0.0185(8) Uani 1 1 d . . . . .
C42 C 0.2706(5) 0.6211(4) 0.5551(3) 0.0247(9) Uani 1 1 d . . . . .
H42 H 0.220949 0.554459 0.565570 0.030 Uiso 1 1 calc R U . . .
C43 C 0.2437(5) 0.6894(4) 0.6113(3) 0.0267(10) Uani 1 1 d . . . . .
H43 H 0.175740 0.667305 0.660120 0.032 Uiso 1 1 calc R U . . .
C44 C 0.4049(5) 0.4018(4) 0.3840(3) 0.0257(10) Uani 1 1 d . . . . .
H44 H 0.377180 0.327590 0.398622 0.031 Uiso 1 1 calc R U . . .
C45 C 0.3705(4) 0.4672(4) 0.4419(3) 0.0217(9) Uani 1 1 d . . . . .
H45 H 0.322465 0.437519 0.494784 0.026 Uiso 1 1 calc R U . . .
C46 C 0.4068(4) 0.5773(4) 0.4224(2) 0.0183(8) Uani 1 1 d . . . . .
C47 C 0.4800(5) 0.6143(4) 0.3438(3) 0.0221(9) Uani 1 1 d . . . . .
H47 H 0.507575 0.688397 0.327210 0.027 Uiso 1 1 calc R U . . .
C48 C 0.5119(5) 0.5414(4) 0.2901(3) 0.0248(10) Uani 1 1 d . . . . .
H48 H 0.562978 0.567822 0.237129 0.030 Uiso 1 1 calc R U . . .
H1 H 0.919(6) 0.592(5) 0.321(3) 0.029(15) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.434(3) . ?
S1 O1 1.436(3) . ?
S1 N1 1.629(4) . ?
S1 C7 1.772(4) . ?
S2 O3 1.432(3) . ?
S2 O4 1.437(3) . ?
S2 N2 1.624(4) . ?
S2 C21 1.763(4) . ?
F1 C10 1.362(5) . ?
F2 C24 1.370(5) . ?
N1 C1 1.428(5) . ?
N1 H1 0.83(6) . ?
N2 C15 1.429(5) . ?
N2 H2 0.8800 . ?
N3 C29 1.342(6) . ?
N3 C33 1.346(6) . ?
N4 C34 1.343(6) . ?
N4 C38 1.348(6) . ?
N5 C39 1.335(6) . ?
N5 C43 1.335(6) . ?
N6 C48 1.338(6) . ?
N6 C44 1.339(6) . ?
C1 C6 1.393(6) . ?
C1 C2 1.400(6) . ?
C2 C3 1.383(6) . ?
C2 H2A 0.9500 . ?
C3 C4 1.386(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.395(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(6) . ?
C5 C13 1.508(6) . ?
C6 H6 0.9500 . ?
C7 C12 1.389(6) . ?
C7 C8 1.392(6) . ?
C8 C9 1.389(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(6) . ?
C11 C12 1.392(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.522(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C20 1.387(6) . ?
C15 C16 1.401(6) . ?
C16 C17 1.388(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.396(6) . ?
C19 C27 1.514(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(6) . ?
C21 C26 1.399(6) . ?
C22 C23 1.393(6) . ?
C22 H22 0.9500 . ?
C23 C24 1.376(7) . ?
C23 H23 0.9500 . ?
C24 C25 1.378(6) . ?
C25 C26 1.390(6) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.520(6) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.384(7) . ?
C29 H29 0.9500 . ?
C30 C31 1.398(6) . ?
C30 H30 0.9500 . ?
C31 C32 1.393(6) . ?
C31 C36 1.489(6) . ?
C32 C33 1.379(6) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 C35 1.377(7) . ?
C34 H34 0.9500 . ?
C35 C36 1.394(6) . ?
C35 H35 0.9500 . ?
C36 C37 1.402(6) . ?
C37 C38 1.382(7) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 C40 1.381(6) . ?
C39 H39 0.9500 . ?
C40 C41 1.388(6) . ?
C40 H40 0.9500 . ?
C41 C42 1.400(6) . ?
C41 C46 1.481(6) . ?
C42 C43 1.382(6) . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?
C44 C45 1.380(6) . ?
C44 H44 0.9500 . ?
C45 C46 1.395(6) . ?
C45 H45 0.9500 . ?
C46 C47 1.398(6) . ?
C47 C48 1.391(6) . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?

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 119.5(2) . . ?
O2 S1 N1 104.4(2) . . ?
O1 S1 N1 109.6(2) . . ?
O2 S1 C7 108.4(2) . . ?
O1 S1 C7 107.9(2) . . ?
N1 S1 C7 106.30(19) . . ?
O3 S2 O4 119.28(19) . . ?
O3 S2 N2 109.77(19) . . ?
O4 S2 N2 104.43(19) . . ?
O3 S2 C21 107.26(19) . . ?
O4 S2 C21 108.82(19) . . ?
N2 S2 C21 106.65(19) . . ?
C1 N1 S1 122.8(3) . . ?
C1 N1 H1 122(4) . . ?
S1 N1 H1 106(4) . . ?
C15 N2 S2 122.7(3) . . ?
C15 N2 H2 118.6 . . ?
S2 N2 H2 118.6 . . ?
C29 N3 C33 115.9(4) . . ?
C34 N4 C38 115.9(4) . . ?
C39 N5 C43 116.5(4) . . ?
C48 N6 C44 116.3(4) . . ?
C6 C1 C2 119.7(4) . . ?
C6 C1 N1 122.3(4) . . ?
C2 C1 N1 117.8(4) . . ?
C3 C2 C1 119.7(4) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 120.7(4) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 120.2(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 119.2(4) . . ?
C4 C5 C13 121.1(4) . . ?
C6 C5 C13 119.5(4) . . ?
C1 C6 C5 120.3(4) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C12 C7 C8 121.6(4) . . ?
C12 C7 S1 118.1(3) . . ?
C8 C7 S1 120.3(3) . . ?
C9 C8 C7 119.1(4) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C10 C9 C8 118.3(4) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
F1 C10 C11 118.1(4) . . ?
F1 C10 C9 118.2(4) . . ?
C11 C10 C9 123.7(4) . . ?
C10 C11 C12 117.9(4) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
C7 C12 C11 119.4(4) . . ?
C7 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C5 C13 C14 111.8(4) . . ?
C5 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
C5 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 119.8(4) . . ?
C20 C15 N2 121.2(4) . . ?
C16 C15 N2 118.9(4) . . ?
C17 C16 C15 119.1(4) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C18 120.4(4) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 121.2(4) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 118.2(4) . . ?
C18 C19 C27 123.9(4) . . ?
C20 C19 C27 118.0(4) . . ?
C15 C20 C19 121.4(4) . . ?
C15 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C22 C21 C26 121.0(4) . . ?
C22 C21 S2 120.8(3) . . ?
C26 C21 S2 118.2(3) . . ?
C21 C22 C23 119.8(4) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 117.8(4) . . ?
C24 C23 H23 121.1 . . ?
C22 C23 H23 121.1 . . ?
F2 C24 C23 118.4(4) . . ?
F2 C24 C25 117.6(4) . . ?
C23 C24 C25 124.0(4) . . ?
C24 C25 C26 117.9(4) . . ?
C24 C25 H25 121.0 . . ?
C26 C25 H25 121.0 . . ?
C25 C26 C21 119.5(4) . . ?
C25 C26 H26 120.3 . . ?
C21 C26 H26 120.3 . . ?
C19 C27 C28 116.3(4) . . ?
C19 C27 H27A 108.2 . . ?
C28 C27 H27A 108.2 . . ?
C19 C27 H27B 108.2 . . ?
C28 C27 H27B 108.2 . . ?
H27A C27 H27B 107.4 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N3 C29 C30 124.1(4) . . ?
N3 C29 H29 118.0 . . ?
C30 C29 H29 118.0 . . ?
C29 C30 C31 119.4(4) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 H30 120.3 . . ?
C32 C31 C30 116.7(4) . . ?
C32 C31 C36 121.9(4) . . ?
C30 C31 C36 121.4(4) . . ?
C33 C32 C31 119.8(4) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
N3 C33 C32 124.0(4) . . ?
N3 C33 H33 118.0 . . ?
C32 C33 H33 118.0 . . ?
N4 C34 C35 124.1(5) . . ?
N4 C34 H34 117.9 . . ?
C35 C34 H34 117.9 . . ?
C34 C35 C36 119.6(4) . . ?
C34 C35 H35 120.2 . . ?
C36 C35 H35 120.2 . . ?
C35 C36 C37 117.1(4) . . ?
C35 C36 C31 121.1(4) . . ?
C37 C36 C31 121.8(4) . . ?
C38 C37 C36 119.0(4) . . ?
C38 C37 H37 120.5 . . ?
C36 C37 H37 120.5 . . ?
N4 C38 C37 124.2(4) . . ?
N4 C38 H38 117.9 . . ?
C37 C38 H38 117.9 . . ?
N5 C39 C40 123.9(4) . . ?
N5 C39 H39 118.1 . . ?
C40 C39 H39 118.1 . . ?
C39 C40 C41 120.0(4) . . ?
C39 C40 H40 120.0 . . ?
C41 C40 H40 120.0 . . ?
C40 C41 C42 116.1(4) . . ?
C40 C41 C46 122.4(4) . . ?
C42 C41 C46 121.4(4) . . ?
C43 C42 C41 119.9(4) . . ?
C43 C42 H42 120.1 . . ?
C41 C42 H42 120.1 . . ?
N5 C43 C42 123.6(4) . . ?
N5 C43 H43 118.2 . . ?
C42 C43 H43 118.2 . . ?
N6 C44 C45 124.2(4) . . ?
N6 C44 H44 117.9 . . ?
C45 C44 H44 117.9 . . ?
C44 C45 C46 119.6(4) . . ?
C44 C45 H45 120.2 . . ?
C46 C45 H45 120.2 . . ?
C45 C46 C47 116.8(4) . . ?
C45 C46 C41 121.3(4) . . ?
C47 C46 C41 122.0(4) . . ?
C48 C47 C46 119.3(4) . . ?
C48 C47 H47 120.4 . . ?
C46 C47 H47 120.4 . . ?
N6 C48 C47 123.9(4) . . ?
N6 C48 H48 118.0 . . ?
C47 C48 H48 118.0 . . ?

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
O2 S1 N1 C1 174.6(3) . . . . ?
O1 S1 N1 C1 -56.2(4) . . . . ?
C7 S1 N1 C1 60.1(4) . . . . ?
O3 S2 N2 C15 -54.6(4) . . . . ?
O4 S2 N2 C15 176.4(3) . . . . ?
C21 S2 N2 C15 61.3(4) . . . . ?
S1 N1 C1 C6 51.2(5) . . . . ?
S1 N1 C1 C2 -132.0(4) . . . . ?
C6 C1 C2 C3 -0.4(6) . . . . ?
N1 C1 C2 C3 -177.3(4) . . . . ?
C1 C2 C3 C4 -0.4(7) . . . . ?
C2 C3 C4 C5 0.6(7) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
C3 C4 C5 C13 174.7(4) . . . . ?
C2 C1 C6 C5 1.0(6) . . . . ?
N1 C1 C6 C5 177.7(4) . . . . ?
C4 C5 C6 C1 -0.7(6) . . . . ?
C13 C5 C6 C1 -175.6(4) . . . . ?
O2 S1 C7 C12 -50.3(4) . . . . ?
O1 S1 C7 C12 178.9(3) . . . . ?
N1 S1 C7 C12 61.4(4) . . . . ?
O2 S1 C7 C8 129.2(4) . . . . ?
O1 S1 C7 C8 -1.5(4) . . . . ?
N1 S1 C7 C8 -119.0(4) . . . . ?
C12 C7 C8 C9 1.5(6) . . . . ?
S1 C7 C8 C9 -178.0(3) . . . . ?
C7 C8 C9 C10 -1.0(6) . . . . ?
C8 C9 C10 F1 -179.7(4) . . . . ?
C8 C9 C10 C11 0.1(7) . . . . ?
F1 C10 C11 C12 -179.8(4) . . . . ?
C9 C10 C11 C12 0.3(7) . . . . ?
C8 C7 C12 C11 -1.1(7) . . . . ?
S1 C7 C12 C11 178.5(3) . . . . ?
C10 C11 C12 C7 0.1(7) . . . . ?
C4 C5 C13 C14 -92.6(5) . . . . ?
C6 C5 C13 C14 82.2(5) . . . . ?
S2 N2 C15 C20 60.7(5) . . . . ?
S2 N2 C15 C16 -123.1(4) . . . . ?
C20 C15 C16 C17 1.6(7) . . . . ?
N2 C15 C16 C17 -174.7(4) . . . . ?
C15 C16 C17 C18 -2.1(7) . . . . ?
C16 C17 C18 C19 1.0(7) . . . . ?
C17 C18 C19 C20 0.6(7) . . . . ?
C17 C18 C19 C27 -179.3(4) . . . . ?
C16 C15 C20 C19 0.0(6) . . . . ?
N2 C15 C20 C19 176.2(4) . . . . ?
C18 C19 C20 C15 -1.0(6) . . . . ?
C27 C19 C20 C15 178.8(4) . . . . ?
O3 S2 C21 C22 3.1(4) . . . . ?
O4 S2 C21 C22 133.4(3) . . . . ?
N2 S2 C21 C22 -114.5(3) . . . . ?
O3 S2 C21 C26 -177.7(3) . . . . ?
O4 S2 C21 C26 -47.4(4) . . . . ?
N2 S2 C21 C26 64.7(4) . . . . ?
C26 C21 C22 C23 0.0(6) . . . . ?
S2 C21 C22 C23 179.2(3) . . . . ?
C21 C22 C23 C24 0.2(6) . . . . ?
C22 C23 C24 F2 -178.4(4) . . . . ?
C22 C23 C24 C25 -0.3(7) . . . . ?
F2 C24 C25 C26 178.3(4) . . . . ?
C23 C24 C25 C26 0.1(7) . . . . ?
C24 C25 C26 C21 0.1(6) . . . . ?
C22 C21 C26 C25 -0.2(6) . . . . ?
S2 C21 C26 C25 -179.4(3) . . . . ?
C18 C19 C27 C28 -8.7(7) . . . . ?
C20 C19 C27 C28 171.5(4) . . . . ?
C33 N3 C29 C30 -0.4(7) . . . . ?
N3 C29 C30 C31 1.1(8) . . . . ?
C29 C30 C31 C32 -1.4(7) . . . . ?
C29 C30 C31 C36 177.8(4) . . . . ?
C30 C31 C32 C33 1.1(6) . . . . ?
C36 C31 C32 C33 -178.1(4) . . . . ?
C29 N3 C33 C32 0.1(7) . . . . ?
C31 C32 C33 N3 -0.4(7) . . . . ?
C38 N4 C34 C35 0.4(7) . . . . ?
N4 C34 C35 C36 0.2(7) . . . . ?
C34 C35 C36 C37 -0.6(6) . . . . ?
C34 C35 C36 C31 179.1(4) . . . . ?
C32 C31 C36 C35 156.8(4) . . . . ?
C30 C31 C36 C35 -22.4(6) . . . . ?
C32 C31 C36 C37 -23.5(6) . . . . ?
C30 C31 C36 C37 157.3(4) . . . . ?
C35 C36 C37 C38 0.4(6) . . . . ?
C31 C36 C37 C38 -179.3(4) . . . . ?
C34 N4 C38 C37 -0.6(7) . . . . ?
C36 C37 C38 N4 0.2(7) . . . . ?
C43 N5 C39 C40 -0.1(7) . . . . ?
N5 C39 C40 C41 -0.8(7) . . . . ?
C39 C40 C41 C42 1.6(6) . . . . ?
C39 C40 C41 C46 -177.4(4) . . . . ?
C40 C41 C42 C43 -1.5(7) . . . . ?
C46 C41 C42 C43 177.5(4) . . . . ?
C39 N5 C43 C42 0.2(7) . . . . ?
C41 C42 C43 N5 0.6(8) . . . . ?
C48 N6 C44 C45 -0.2(7) . . . . ?
N6 C44 C45 C46 1.4(7) . . . . ?
C44 C45 C46 C47 -1.3(6) . . . . ?
C44 C45 C46 C41 179.6(4) . . . . ?
C40 C41 C46 C45 162.1(4) . . . . ?
C42 C41 C46 C45 -16.9(6) . . . . ?
C40 C41 C46 C47 -16.9(6) . . . . ?
C42 C41 C46 C47 164.2(4) . . . . ?
C45 C46 C47 C48 0.2(6) . . . . ?
C41 C46 C47 C48 179.2(4) . . . . ?
C44 N6 C48 C47 -1.0(7) . . . . ?
C46 C47 C48 N6 1.0(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N3 . . . 2.961(6) 0.83(6) 2.14(7) 173(5) no
N2 H2 N5 . . . 2.887(6) 0.880 2.204 134.1 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_mfu352-4
_database_code_depnum_ccdc_archive 'CCDC 2087475'
loop_
_audit_author_name
_audit_author_address
'Misaki Okayasu'
;Toho University
Japan
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C20 H19 Cl4 N2 O4 S'
_chemical_formula_moiety         'C20 H19 Cl4 N2 O4 S'
_chemical_formula_weight         525.25
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.56656(14)
_cell_length_b                   11.31930(19)
_cell_length_c                   12.12655(19)
_cell_angle_alpha                85.3760(13)
_cell_angle_beta                 87.7729(13)
_cell_angle_gamma                80.6487(14)
_cell_volume                     1156.08(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    21070
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      29.75
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             538.00
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.749
_exptl_absorpt_correction_T_max  0.910

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            37159
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.579
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5302
_reflns_number_gt                4709
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0967
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         5302
_refine_ls_number_parameters     288
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0497P)²+0.7545P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.78
_refine_diff_density_min         -0.68
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.18226(5) 0.53631(4) 0.37869(3) 0.02710(11) Uani 1 1 d . . . . .
Cl2 Cl 0.97721(7) 0.76104(6) 0.61348(6) 0.05382(17) Uani 1 1 d . . . . .
Cl3 Cl 0.92888(9) 1.00133(7) 0.68462(7) 0.0688(2) Uani 1 1 d . . . . .
Cl4 Cl 0.70778(7) 0.93034(7) 0.53887(6) 0.05639(18) Uani 1 1 d . . . . .
S1 S 0.28470(4) 0.33892(3) 0.79684(3) 0.01514(10) Uani 1 1 d . . . . .
O1 O 0.12549(12) 0.40153(10) 0.80617(9) 0.0188(2) Uani 1 1 d . . . . .
O2 O 0.31812(13) 0.21453(10) 0.83506(9) 0.0207(2) Uani 1 1 d . . . . .
O3 O 0.72990(13) 0.71375(11) 0.87014(10) 0.0245(3) Uani 1 1 d . . . . .
O4 O 0.50489(15) 0.87888(11) 0.79641(12) 0.0298(3) Uani 1 1 d . . . . .
N1 N 0.40184(16) 0.40395(12) 0.86541(11) 0.0161(3) Uani 1 1 d . . . . .
N2 N 0.68454(16) 0.22686(13) 0.90534(12) 0.0223(3) Uani 1 1 d . . . . .
C1 C 0.41713(18) 0.52719(13) 0.84691(12) 0.0155(3) Uani 1 1 d . . . . .
C2 C 0.56515(18) 0.55771(14) 0.86842(12) 0.0170(3) Uani 1 1 d . . . . .
H2 H 0.648603 0.496931 0.893838 0.020 Uiso 1 1 calc R U . . .
C3 C 0.58992(18) 0.67564(14) 0.85279(13) 0.0192(3) Uani 1 1 d . . . . .
C4 C 0.4672(2) 0.76557(14) 0.81411(14) 0.0214(3) Uani 1 1 d . . . . .
C5 C 0.32108(19) 0.73514(14) 0.79509(14) 0.0213(3) Uani 1 1 d . . . . .
H5 H 0.237286 0.795944 0.770259 0.026 Uiso 1 1 calc R U . . .
C6 C 0.29498(18) 0.61618(14) 0.81190(13) 0.0185(3) Uani 1 1 d . . . . .
H6 H 0.193779 0.596562 0.799322 0.022 Uiso 1 1 calc R U . . .
C7 C 0.34535(18) 0.35367(14) 0.65568(12) 0.0162(3) Uani 1 1 d . . . . .
C8 C 0.24877(18) 0.42932(14) 0.58212(13) 0.0181(3) Uani 1 1 d . . . . .
H8 H 0.150171 0.472185 0.605898 0.022 Uiso 1 1 calc R U . . .
C9 C 0.30083(19) 0.44048(14) 0.47233(13) 0.0193(3) Uani 1 1 d . . . . .
C10 C 0.4440(2) 0.37806(15) 0.43674(13) 0.0215(3) Uani 1 1 d . . . . .
H10 H 0.477220 0.386616 0.361253 0.026 Uiso 1 1 calc R U . . .
C11 C 0.5386(2) 0.30303(15) 0.51200(14) 0.0229(3) Uani 1 1 d . . . . .
H11 H 0.636920 0.260016 0.487839 0.028 Uiso 1 1 calc R U . . .
C12 C 0.49087(18) 0.29019(14) 0.62250(13) 0.0197(3) Uani 1 1 d . . . . .
H12 H 0.555860 0.239285 0.674397 0.024 Uiso 1 1 calc R U . . .
C13 C 0.86202(19) 0.62295(17) 0.89811(15) 0.0263(4) Uani 1 1 d . . . . .
H13A H 0.954997 0.660734 0.908488 0.032 Uiso 1 1 calc R U . . .
H13B H 0.837305 0.577003 0.966746 0.032 Uiso 1 1 calc R U . . .
H13C H 0.884235 0.568918 0.838232 0.032 Uiso 1 1 calc R U . . .
C14 C 0.3907(3) 0.96511(16) 0.7374(2) 0.0414(5) Uani 1 1 d . . . . .
H14A H 0.427843 1.042855 0.728838 0.050 Uiso 1 1 calc R U . . .
H14B H 0.376642 0.938020 0.664187 0.050 Uiso 1 1 calc R U . . .
H14C H 0.289393 0.973427 0.778751 0.050 Uiso 1 1 calc R U . . .
C15 C 0.6594(2) 0.11744(18) 0.94365(18) 0.0337(4) Uani 1 1 d . . . . .
H15 H 0.553890 0.101208 0.945758 0.040 Uiso 1 1 calc R U . . .
C16 C 0.7779(2) 0.02623(17) 0.98049(18) 0.0348(5) Uani 1 1 d . . . . .
H16 H 0.753004 -0.050253 1.006036 0.042 Uiso 1 1 calc R U . . .
C17 C 0.93396(18) 0.04712(14) 0.97993(13) 0.0194(3) Uani 1 1 d . . . . .
C18 C 0.96052(19) 0.16067(15) 0.93916(15) 0.0229(3) Uani 1 1 d . . . . .
H18 H 1.064671 0.179710 0.936098 0.027 Uiso 1 1 calc R U . . .
C19 C 0.8346(2) 0.24593(15) 0.90300(15) 0.0246(4) Uani 1 1 d . . . . .
H19 H 0.856110 0.322571 0.874863 0.029 Uiso 1 1 calc R U . . .
C20 C 0.8353(2) 0.8831(2) 0.64888(19) 0.0392(5) Uani 1 1 d . . . . .
H1 H 0.481(3) 0.357(2) 0.8792(18) 0.027(5) Uiso 1 1 d . . . . .
H20 H 0.779(3) 0.860(3) 0.713(2) 0.060(8) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C9 1.7409(16) . ?
Cl2 C20 1.755(2) . ?
Cl3 C20 1.758(2) . ?
Cl4 C20 1.751(2) . ?
S1 O2 1.4329(12) . ?
S1 O1 1.4360(11) . ?
S1 N1 1.6261(13) . ?
S1 C7 1.7723(15) . ?
O3 C3 1.3677(19) . ?
O3 C13 1.431(2) . ?
O4 C4 1.3713(19) . ?
O4 C14 1.433(3) . ?
N1 C1 1.4213(19) . ?
N1 H1 0.80(2) . ?
N2 C15 1.335(2) . ?
N2 C19 1.336(2) . ?
C1 C6 1.383(2) . ?
C1 C2 1.406(2) . ?
C2 C3 1.382(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.405(2) . ?
C4 C5 1.383(2) . ?
C5 C6 1.398(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.385(2) . ?
C7 C12 1.396(2) . ?
C8 C9 1.390(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(2) . ?
C10 C11 1.386(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.395(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(2) . ?
C17 C17 1.491(3) 2_757 ?
C18 C19 1.385(2) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20 0.94(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
O2 S1 O1 119.10(7) . . ?
O2 S1 N1 104.89(7) . . ?
O1 S1 N1 109.67(7) . . ?
O2 S1 C7 108.36(7) . . ?
O1 S1 C7 107.48(7) . . ?
N1 S1 C7 106.74(7) . . ?
C3 O3 C13 116.84(13) . . ?
C4 O4 C14 115.47(14) . . ?
C1 N1 S1 123.94(11) . . ?
C1 N1 H1 117.4(16) . . ?
S1 N1 H1 108.9(15) . . ?
C15 N2 C19 116.26(15) . . ?
C6 C1 C2 119.67(14) . . ?
C6 C1 N1 123.63(14) . . ?
C2 C1 N1 116.68(14) . . ?
C3 C2 C1 120.38(15) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
O3 C3 C2 124.62(15) . . ?
O3 C3 C4 115.43(14) . . ?
C2 C3 C4 119.94(14) . . ?
O4 C4 C5 124.92(16) . . ?
O4 C4 C3 115.76(15) . . ?
C5 C4 C3 119.31(15) . . ?
C4 C5 C6 120.94(15) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 119.72(15) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C8 C7 C12 121.99(14) . . ?
C8 C7 S1 119.19(12) . . ?
C12 C7 S1 118.81(12) . . ?
C7 C8 C9 117.82(14) . . ?
C7 C8 H8 121.1 . . ?
C9 C8 H8 121.1 . . ?
C10 C9 C8 121.55(15) . . ?
C10 C9 Cl1 119.85(12) . . ?
C8 C9 Cl1 118.60(12) . . ?
C9 C10 C11 119.52(15) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 120.53(15) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 118.59(15) . . ?
C11 C12 H12 120.7 . . ?
C7 C12 H12 120.7 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 C16 123.90(16) . . ?
N2 C15 H15 118.1 . . ?
C16 C15 H15 118.1 . . ?
C15 C16 C17 119.71(16) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 116.45(15) . . ?
C18 C17 C17 121.47(18) . 2_757 ?
C16 C17 C17 122.07(18) . 2_757 ?
C19 C18 C17 119.74(15) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
N2 C19 C18 123.92(15) . . ?
N2 C19 H19 118.0 . . ?
C18 C19 H19 118.0 . . ?
Cl4 C20 Cl2 110.12(13) . . ?
Cl4 C20 Cl3 110.78(13) . . ?
Cl2 C20 Cl3 110.18(12) . . ?
Cl4 C20 H20 110.7(18) . . ?
Cl2 C20 H20 108.9(17) . . ?
Cl3 C20 H20 106.1(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
O2 S1 N1 C1 174.78(12) . . . . ?
O1 S1 N1 C1 -56.22(14) . . . . ?
C7 S1 N1 C1 59.92(14) . . . . ?
S1 N1 C1 C6 31.4(2) . . . . ?
S1 N1 C1 C2 -150.01(12) . . . . ?
C6 C1 C2 C3 -1.2(2) . . . . ?
N1 C1 C2 C3 -179.86(13) . . . . ?
C13 O3 C3 C2 5.1(2) . . . . ?
C13 O3 C3 C4 -173.52(14) . . . . ?
C1 C2 C3 O3 -179.17(13) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C14 O4 C4 C5 -10.5(2) . . . . ?
C14 O4 C4 C3 168.44(16) . . . . ?
O3 C3 C4 O4 1.5(2) . . . . ?
C2 C3 C4 O4 -177.17(13) . . . . ?
O3 C3 C4 C5 -179.53(14) . . . . ?
C2 C3 C4 C5 1.8(2) . . . . ?
O4 C4 C5 C6 177.73(15) . . . . ?
C3 C4 C5 C6 -1.2(2) . . . . ?
C2 C1 C6 C5 1.9(2) . . . . ?
N1 C1 C6 C5 -179.57(14) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
O2 S1 C7 C8 137.58(12) . . . . ?
O1 S1 C7 C8 7.66(14) . . . . ?
N1 S1 C7 C8 -109.93(13) . . . . ?
O2 S1 C7 C12 -43.63(14) . . . . ?
O1 S1 C7 C12 -173.55(12) . . . . ?
N1 S1 C7 C12 68.86(14) . . . . ?
C12 C7 C8 C9 0.2(2) . . . . ?
S1 C7 C8 C9 178.96(11) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C7 C8 C9 Cl1 -179.34(11) . . . . ?
C8 C9 C10 C11 -0.3(2) . . . . ?
Cl1 C9 C10 C11 179.26(12) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C10 C11 C12 C7 0.5(2) . . . . ?
C8 C7 C12 C11 -0.6(2) . . . . ?
S1 C7 C12 C11 -179.33(12) . . . . ?
C19 N2 C15 C16 0.4(3) . . . . ?
N2 C15 C16 C17 0.8(4) . . . . ?
C15 C16 C17 C18 -1.3(3) . . . . ?
C15 C16 C17 C17 179.1(2) . . . 2_757 ?
C16 C17 C18 C19 0.6(3) . . . . ?
C17 C17 C18 C19 -179.76(19) 2_757 . . . ?
C15 N2 C19 C18 -1.1(3) . . . . ?
C17 C18 C19 N2 0.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N2 . . . 2.9111(18) 0.80(2) 2.11(2) 176(2) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_mfu352-3
_database_code_depnum_ccdc_archive 'CCDC 2087481'
loop_
_audit_author_name
_audit_author_address
'Misaki Okayasu'
;Toho University
Japan
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C23 H18 F3 N3 O2 S'
_chemical_formula_moiety         'C23 H18 F3 N3 O2 S'
_chemical_formula_weight         457.47
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.24874(18)
_cell_length_b                   9.01497(18)
_cell_length_c                   29.4840(6)
_cell_angle_alpha                82.9508(16)
_cell_angle_beta                 83.6918(18)
_cell_angle_gamma                76.4332(18)
_cell_volume                     2107.72(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25146
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      29.06
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944.00
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.850
_exptl_absorpt_correction_T_max  0.986

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            70682
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.586
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       37
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             9659
_reflns_number_gt                7960
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1257
_refine_ls_wR_factor_gt          0.1213
_refine_ls_number_restraints     18
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         9659
_refine_ls_number_parameters     611
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0303P)²+3.3504P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.43
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.78926(6) 0.11514(6) 0.61509(2) 0.01620(12) Uani 1 1 d . . . . .
S2 S 0.69253(7) 0.73026(6) 0.87689(2) 0.01813(12) Uani 1 1 d . . . . .
F2 F 0.28810(18) 0.20264(18) 0.80661(5) 0.0310(3) Uani 1 1 d . . . . .
F3 F 0.13251(18) 0.36226(19) 0.76012(5) 0.0346(4) Uani 1 1 d . . . . .
O1 O 0.7600(2) 0.23042(18) 0.57691(5) 0.0215(3) Uani 1 1 d . . . . .
F1 F 0.3230(2) 0.43222(19) 0.79107(6) 0.0395(4) Uani 1 1 d . . . . .
O2 O 0.95324(19) 0.06664(19) 0.63110(6) 0.0224(4) Uani 1 1 d . . . . .
O4 O 0.8579(2) 0.70020(19) 0.85415(6) 0.0243(4) Uani 1 1 d . . . . .
O3 O 0.6461(2) 0.62479(19) 0.91345(6) 0.0247(4) Uani 1 1 d . . . . .
N1 N 0.7315(2) -0.0314(2) 0.59969(6) 0.0174(4) Uani 1 1 d . . . . .
H1 H 0.644(3) 0.003(3) 0.5842(9) 0.021 Uiso 1 1 d . U . . .
N2 N 0.4395(2) 0.1093(2) 0.54787(6) 0.0205(4) Uani 1 1 d . . . . .
N4 N 0.6589(2) 0.8947(2) 0.89868(7) 0.0184(4) Uani 1 1 d . . . . .
H4 H 0.566(4) 0.908(3) 0.9145(9) 0.022 Uiso 1 1 d . U . . .
F4 F 0.0402(7) 0.8858(7) 0.75133(18) 0.0573(16) Uani 0.790(9) 1 d . . P A 1
F6 F 0.1997(4) 0.7068(4) 0.71593(13) 0.0474(9) Uani 0.790(9) 1 d . . P A 1
N5 N 0.3387(3) 0.9277(2) 0.95394(7) 0.0262(4) Uani 1 1 d . . . . .
N6 N -0.2603(3) 0.5331(2) 1.07298(8) 0.0281(5) Uani 1 1 d . . . . .
N3 N -0.1996(3) 0.4897(2) 0.40186(7) 0.0264(5) Uani 1 1 d . . . . .
F5 F 0.2293(4) 0.9344(5) 0.69897(11) 0.0568(13) Uani 0.790(9) 1 d . . P A 1
C44 C -0.0305(3) 0.6997(3) 1.02624(8) 0.0188(4) Uani 1 1 d . . . . .
C30 C 0.5494(3) 0.7562(2) 0.83451(7) 0.0165(4) Uani 1 1 d . . . . .
C1 C 0.7239(3) -0.1660(2) 0.63024(7) 0.0171(4) Uani 1 1 d . . . . .
C11 C 0.5750(3) 0.1859(3) 0.74252(8) 0.0193(4) Uani 1 1 d . . . . .
H11 H 0.604250 0.162665 0.773282 0.023 Uiso 1 1 calc R U . . .
C39 C 0.0946(3) 0.7806(3) 1.00135(8) 0.0189(4) Uani 1 1 d . . . . .
C12 C 0.6923(3) 0.1408(3) 0.70650(8) 0.0187(4) Uani 1 1 d . . . . .
H12 H 0.802378 0.085743 0.712308 0.022 Uiso 1 1 calc R U . . .
C29 C 0.5768(3) 1.1688(3) 0.87989(8) 0.0200(5) Uani 1 1 d . . . . .
H29 H 0.472802 1.167598 0.897156 0.024 Uiso 1 1 calc R U . . .
C10 C 0.4138(3) 0.2656(3) 0.73321(8) 0.0186(4) Uani 1 1 d . . . . .
C15 C 0.1601(3) 0.1482(3) 0.52535(8) 0.0199(5) Uani 1 1 d . . . . .
H15 H 0.054975 0.120202 0.530263 0.024 Uiso 1 1 calc R U . . .
C31 C 0.3900(3) 0.7298(2) 0.84765(8) 0.0180(4) Uani 1 1 d . . . . .
H31 H 0.361001 0.693706 0.878418 0.022 Uiso 1 1 calc R U . . .
C24 C 0.6944(3) 1.0317(3) 0.87445(7) 0.0173(4) Uani 1 1 d . . . . .
C16 C 0.1872(3) 0.2605(2) 0.49001(7) 0.0164(4) Uani 1 1 d . . . . .
C32 C 0.2749(3) 0.7570(3) 0.81505(8) 0.0209(5) Uani 1 1 d . . . . .
H32 H 0.166120 0.738780 0.823264 0.025 Uiso 1 1 calc R U . . .
C9 C 0.3696(3) 0.3029(3) 0.68851(8) 0.0209(5) Uani 1 1 d . . . . .
H9 H 0.259757 0.358682 0.682656 0.025 Uiso 1 1 calc R U . . .
C7 C 0.6466(3) 0.1771(2) 0.66193(7) 0.0162(4) Uani 1 1 d . . . . .
C45 C -0.0279(3) 0.6524(3) 1.07311(8) 0.0243(5) Uani 1 1 d . . . . .
H45 H 0.051955 0.676279 1.090293 0.029 Uiso 1 1 calc R U . . .
C38 C 0.0680(3) 0.8672(3) 0.95914(8) 0.0211(5) Uani 1 1 d . . . . .
H38 H -0.034130 0.878076 0.945655 0.025 Uiso 1 1 calc R U . . .
C35 C 0.5953(3) 0.8073(3) 0.78972(8) 0.0203(5) Uani 1 1 d . . . . .
H35 H 0.704885 0.823154 0.781291 0.024 Uiso 1 1 calc R U . . .
C21 C 0.0536(3) 0.3400(2) 0.45979(7) 0.0165(4) Uani 1 1 d . . . . .
C22 C 0.0560(3) 0.4817(3) 0.43557(8) 0.0202(5) Uani 1 1 d . . . . .
H22 H 0.143889 0.531251 0.438145 0.024 Uiso 1 1 calc R U . . .
C42 C -0.2638(3) 0.5809(3) 1.02819(9) 0.0260(5) Uani 1 1 d . . . . .
H42 H -0.346857 0.557290 1.012142 0.031 Uiso 1 1 calc R U . . .
C17 C 0.3444(3) 0.2955(3) 0.48532(8) 0.0202(5) Uani 1 1 d . . . . .
H17 H 0.369082 0.372405 0.462318 0.024 Uiso 1 1 calc R U . . .
C40 C 0.2466(3) 0.7718(3) 1.01938(8) 0.0237(5) Uani 1 1 d . . . . .
H40 H 0.270452 0.715334 1.048174 0.028 Uiso 1 1 calc R U . . .
C37 C 0.1913(3) 0.9369(3) 0.93714(8) 0.0243(5) Uani 1 1 d . . . . .
H37 H 0.170761 0.994875 0.908379 0.029 Uiso 1 1 calc R U . . .
C20 C -0.0802(3) 0.2748(3) 0.45439(8) 0.0241(5) Uani 1 1 d . . . . .
H20 H -0.088210 0.178076 0.470188 0.029 Uiso 1 1 calc R U . . .
C8 C 0.4862(3) 0.2583(3) 0.65247(8) 0.0198(5) Uani 1 1 d . . . . .
H8 H 0.457347 0.282714 0.621698 0.024 Uiso 1 1 calc R U . . .
C14 C 0.2864(3) 0.0783(3) 0.55303(8) 0.0218(5) Uani 1 1 d . . . . .
H14 H 0.263910 0.003962 0.577173 0.026 Uiso 1 1 calc R U . . .
C33 C 0.3192(3) 0.8113(3) 0.77018(8) 0.0215(5) Uani 1 1 d . . . . .
C6 C 0.5866(3) -0.2307(3) 0.62927(8) 0.0209(5) Uani 1 1 d . . . . .
H6 H 0.499490 -0.181536 0.610332 0.025 Uiso 1 1 calc R U . . .
C13 C 0.2897(3) 0.3156(3) 0.77243(8) 0.0231(5) Uani 1 1 d . . . . .
C23 C -0.0712(3) 0.5503(3) 0.40754(8) 0.0234(5) Uani 1 1 d . . . . .
H23 H -0.066604 0.647148 0.391280 0.028 Uiso 1 1 calc R U . . .
C2 C 0.8502(3) -0.2363(3) 0.65853(8) 0.0210(5) Uani 1 1 d . . . . .
H2 H 0.944257 -0.193000 0.659229 0.025 Uiso 1 1 calc R U . . .
C43 C -0.1544(3) 0.6623(3) 1.00385(8) 0.0220(5) Uani 1 1 d . . . . .
H43 H -0.163145 0.692792 0.972049 0.026 Uiso 1 1 calc R U . . .
C18 C 0.4644(3) 0.2178(3) 0.51432(8) 0.0229(5) Uani 1 1 d . . . . .
H18 H 0.570980 0.243015 0.510152 0.027 Uiso 1 1 calc R U . . .
C34 C 0.4783(3) 0.8351(3) 0.75724(8) 0.0226(5) Uani 1 1 d . . . . .
H34 H 0.507582 0.870151 0.726388 0.027 Uiso 1 1 calc R U . . .
C28 C 0.6115(3) 1.3065(3) 0.86018(8) 0.0251(5) Uani 1 1 d . . . . .
H28 H 0.532615 1.399880 0.864892 0.030 Uiso 1 1 calc R U . . .
C25 C 0.8452(3) 1.0343(3) 0.84850(8) 0.0235(5) Uani 1 1 d . . . . .
H25 H 0.926639 0.941671 0.844956 0.028 Uiso 1 1 calc R U . . .
C19 C -0.2008(3) 0.3534(3) 0.42566(9) 0.0281(5) Uani 1 1 d . . . . .
H19 H -0.290960 0.307394 0.422595 0.034 Uiso 1 1 calc R U . . .
C3 C 0.8366(3) -0.3711(3) 0.68584(8) 0.0260(5) Uani 1 1 d . . . . .
H3 H 0.921336 -0.418549 0.705703 0.031 Uiso 1 1 calc R U . . .
C27 C 0.7598(3) 1.3094(3) 0.83373(9) 0.0279(5) Uani 1 1 d . . . . .
H27 H 0.782115 1.404009 0.819677 0.033 Uiso 1 1 calc R U . . .
C26 C 0.8763(3) 1.1727(3) 0.82783(9) 0.0286(5) Uani 1 1 d . . . . .
H26 H 0.978108 1.174127 0.809459 0.034 Uiso 1 1 calc R U . . .
C5 C 0.5771(3) -0.3668(3) 0.65593(9) 0.0272(5) Uani 1 1 d . . . . .
H5 H 0.484940 -0.412125 0.654628 0.033 Uiso 1 1 calc R U . . .
C46 C -0.1425(3) 0.5706(3) 1.09430(9) 0.0286(6) Uani 1 1 d . . . . .
H46 H -0.137359 0.538802 1.126139 0.034 Uiso 1 1 calc R U . . .
C41 C 0.3621(3) 0.8466(3) 0.99472(9) 0.0275(5) Uani 1 1 d . . . . .
H41 H 0.464463 0.839883 1.007636 0.033 Uiso 1 1 calc R U . . .
C4 C 0.7020(3) -0.4368(3) 0.68451(9) 0.0284(5) Uani 1 1 d . . . . .
H4A H 0.695084 -0.529366 0.703050 0.034 Uiso 1 1 calc R U . . .
C36 C 0.1949(3) 0.8392(3) 0.73492(10) 0.0337(6) Uani 1 1 d . . . . .
F7 F 0.138(2) 1.0027(14) 0.7260(6) 0.074(6) Uani 0.210(9) 1 d . U P A 2
F8 F 0.2227(14) 0.788(3) 0.7007(4) 0.068(6) Uani 0.210(9) 1 d . U P A 2
F9 F 0.042(3) 0.820(3) 0.7557(9) 0.074(7) Uani 0.210(9) 1 d . U P A 2


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.4339(16) . ?
S1 O1 1.4354(16) . ?
S1 N1 1.6332(19) . ?
S1 C7 1.769(2) . ?
S2 O3 1.4288(17) . ?
S2 O4 1.4334(17) . ?
S2 N4 1.639(2) . ?
S2 C30 1.770(2) . ?
F2 C13 1.343(3) . ?
F3 C13 1.342(3) . ?
F1 C13 1.339(3) . ?
N1 C1 1.429(3) . ?
N1 H1 0.87(3) . ?
N2 C18 1.338(3) . ?
N2 C14 1.345(3) . ?
N4 C24 1.425(3) . ?
N4 H4 0.85(3) . ?
F4 C36 1.305(6) . ?
F6 C36 1.369(4) . ?
N5 C41 1.336(3) . ?
N5 C37 1.343(3) . ?
N6 C46 1.339(3) . ?
N6 C42 1.339(3) . ?
N3 C23 1.334(3) . ?
N3 C19 1.340(3) . ?
F5 C36 1.329(4) . ?
C44 C45 1.396(3) . ?
C44 C43 1.399(3) . ?
C44 C39 1.480(3) . ?
C30 C35 1.387(3) . ?
C30 C31 1.395(3) . ?
C1 C2 1.390(3) . ?
C1 C6 1.395(3) . ?
C11 C12 1.388(3) . ?
C11 C10 1.394(3) . ?
C11 H11 0.9500 . ?
C39 C38 1.396(3) . ?
C39 C40 1.397(3) . ?
C12 C7 1.386(3) . ?
C12 H12 0.9500 . ?
C29 C28 1.384(3) . ?
C29 C24 1.395(3) . ?
C29 H29 0.9500 . ?
C10 C9 1.386(3) . ?
C10 C13 1.496(3) . ?
C15 C14 1.379(3) . ?
C15 C16 1.398(3) . ?
C15 H15 0.9500 . ?
C31 C32 1.385(3) . ?
C31 H31 0.9500 . ?
C24 C25 1.391(3) . ?
C16 C17 1.394(3) . ?
C16 C21 1.487(3) . ?
C32 C33 1.393(3) . ?
C32 H32 0.9500 . ?
C9 C8 1.384(3) . ?
C9 H9 0.9500 . ?
C7 C8 1.393(3) . ?
C45 C46 1.383(4) . ?
C45 H45 0.9500 . ?
C38 C37 1.380(3) . ?
C38 H38 0.9500 . ?
C35 C34 1.393(3) . ?
C35 H35 0.9500 . ?
C21 C22 1.388(3) . ?
C21 C20 1.398(3) . ?
C22 C23 1.388(3) . ?
C22 H22 0.9500 . ?
C42 C43 1.381(3) . ?
C42 H42 0.9500 . ?
C17 C18 1.384(3) . ?
C17 H17 0.9500 . ?
C40 C41 1.386(3) . ?
C40 H40 0.9500 . ?
C37 H37 0.9500 . ?
C20 C19 1.384(3) . ?
C20 H20 0.9500 . ?
C8 H8 0.9500 . ?
C14 H14 0.9500 . ?
C33 C34 1.385(3) . ?
C33 C36 1.498(3) . ?
C6 C5 1.387(3) . ?
C6 H6 0.9500 . ?
C23 H23 0.9500 . ?
C2 C3 1.393(3) . ?
C2 H2 0.9500 . ?
C43 H43 0.9500 . ?
C18 H18 0.9500 . ?
C34 H34 0.9500 . ?
C28 C27 1.381(4) . ?
C28 H28 0.9500 . ?
C25 C26 1.387(3) . ?
C25 H25 0.9500 . ?
C19 H19 0.9500 . ?
C3 C4 1.382(4) . ?
C3 H3 0.9500 . ?
C27 C26 1.390(4) . ?
C27 H27 0.9500 . ?
C26 H26 0.9500 . ?
C5 C4 1.388(4) . ?
C5 H5 0.9500 . ?
C46 H46 0.9500 . ?
C41 H41 0.9500 . ?
C4 H4A 0.9500 . ?
C36 F8 1.137(11) . ?
C36 F9 1.38(2) . ?
C36 F7 1.439(12) . ?

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 119.62(10) . . ?
O2 S1 N1 109.86(10) . . ?
O1 S1 N1 104.64(10) . . ?
O2 S1 C7 108.00(10) . . ?
O1 S1 C7 108.39(10) . . ?
N1 S1 C7 105.45(10) . . ?
O3 S2 O4 120.38(10) . . ?
O3 S2 N4 105.36(10) . . ?
O4 S2 N4 108.49(10) . . ?
O3 S2 C30 108.07(10) . . ?
O4 S2 C30 107.54(10) . . ?
N4 S2 C30 106.18(10) . . ?
C1 N1 S1 122.57(15) . . ?
C1 N1 H1 113.9(17) . . ?
S1 N1 H1 108.6(17) . . ?
C18 N2 C14 116.17(19) . . ?
C24 N4 S2 124.48(16) . . ?
C24 N4 H4 114.0(18) . . ?
S2 N4 H4 108.6(19) . . ?
C41 N5 C37 116.2(2) . . ?
C46 N6 C42 115.9(2) . . ?
C23 N3 C19 115.4(2) . . ?
C45 C44 C43 116.5(2) . . ?
C45 C44 C39 121.6(2) . . ?
C43 C44 C39 121.9(2) . . ?
C35 C30 C31 121.6(2) . . ?
C35 C30 S2 119.67(17) . . ?
C31 C30 S2 118.66(17) . . ?
C2 C1 C6 120.1(2) . . ?
C2 C1 N1 122.6(2) . . ?
C6 C1 N1 117.2(2) . . ?
C12 C11 C10 119.5(2) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C38 C39 C40 117.0(2) . . ?
C38 C39 C44 122.3(2) . . ?
C40 C39 C44 120.7(2) . . ?
C7 C12 C11 119.1(2) . . ?
C7 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C28 C29 C24 120.1(2) . . ?
C28 C29 H29 119.9 . . ?
C24 C29 H29 119.9 . . ?
C9 C10 C11 121.1(2) . . ?
C9 C10 C13 120.1(2) . . ?
C11 C10 C13 118.7(2) . . ?
C14 C15 C16 119.8(2) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C32 C31 C30 118.9(2) . . ?
C32 C31 H31 120.6 . . ?
C30 C31 H31 120.6 . . ?
C25 C24 C29 119.5(2) . . ?
C25 C24 N4 122.4(2) . . ?
C29 C24 N4 117.9(2) . . ?
C17 C16 C15 116.5(2) . . ?
C17 C16 C21 122.1(2) . . ?
C15 C16 C21 121.46(19) . . ?
C31 C32 C33 119.8(2) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C8 C9 C10 119.6(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C12 C7 C8 121.6(2) . . ?
C12 C7 S1 120.67(17) . . ?
C8 C7 S1 117.71(17) . . ?
C46 C45 C44 119.4(2) . . ?
C46 C45 H45 120.3 . . ?
C44 C45 H45 120.3 . . ?
C37 C38 C39 119.4(2) . . ?
C37 C38 H38 120.3 . . ?
C39 C38 H38 120.3 . . ?
C30 C35 C34 119.1(2) . . ?
C30 C35 H35 120.5 . . ?
C34 C35 H35 120.5 . . ?
C22 C21 C20 117.0(2) . . ?
C22 C21 C16 121.7(2) . . ?
C20 C21 C16 121.3(2) . . ?
C21 C22 C23 119.3(2) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
N6 C42 C43 124.1(2) . . ?
N6 C42 H42 117.9 . . ?
C43 C42 H42 117.9 . . ?
C18 C17 C16 119.7(2) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C41 C40 C39 119.1(2) . . ?
C41 C40 H40 120.4 . . ?
C39 C40 H40 120.4 . . ?
N5 C37 C38 124.0(2) . . ?
N5 C37 H37 118.0 . . ?
C38 C37 H37 118.0 . . ?
C19 C20 C21 119.0(2) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C9 C8 C7 119.1(2) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
N2 C14 C15 123.8(2) . . ?
N2 C14 H14 118.1 . . ?
C15 C14 H14 118.1 . . ?
C34 C33 C32 121.0(2) . . ?
C34 C33 C36 119.3(2) . . ?
C32 C33 C36 119.6(2) . . ?
C5 C6 C1 120.1(2) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
F1 C13 F3 106.6(2) . . ?
F1 C13 F2 106.09(19) . . ?
F3 C13 F2 106.56(19) . . ?
F1 C13 C10 112.20(19) . . ?
F3 C13 C10 112.69(19) . . ?
F2 C13 C10 112.21(19) . . ?
N3 C23 C22 124.6(2) . . ?
N3 C23 H23 117.7 . . ?
C22 C23 H23 117.7 . . ?
C1 C2 C3 119.0(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C42 C43 C44 119.7(2) . . ?
C42 C43 H43 120.1 . . ?
C44 C43 H43 120.1 . . ?
N2 C18 C17 124.0(2) . . ?
N2 C18 H18 118.0 . . ?
C17 C18 H18 118.0 . . ?
C33 C34 C35 119.6(2) . . ?
C33 C34 H34 120.2 . . ?
C35 C34 H34 120.2 . . ?
C27 C28 C29 120.5(2) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C26 C25 C24 119.7(2) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
N3 C19 C20 124.8(2) . . ?
N3 C19 H19 117.6 . . ?
C20 C19 H19 117.6 . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C28 C27 C26 119.4(2) . . ?
C28 C27 H27 120.3 . . ?
C26 C27 H27 120.3 . . ?
C25 C26 C27 120.6(2) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
N6 C46 C45 124.5(2) . . ?
N6 C46 H46 117.8 . . ?
C45 C46 H46 117.8 . . ?
N5 C41 C40 124.2(2) . . ?
N5 C41 H41 117.9 . . ?
C40 C41 H41 117.9 . . ?
C3 C4 C5 119.6(2) . . ?
C3 C4 H4A 120.2 . . ?
C5 C4 H4A 120.2 . . ?
F4 C36 F5 109.6(3) . . ?
F4 C36 F6 105.6(4) . . ?
F5 C36 F6 103.3(3) . . ?
F8 C36 F9 110.7(14) . . ?
F8 C36 F7 108.3(11) . . ?
F9 C36 F7 93.6(10) . . ?
F8 C36 C33 123.3(6) . . ?
F4 C36 C33 113.7(3) . . ?
F5 C36 C33 113.1(2) . . ?
F6 C36 C33 110.7(2) . . ?
F9 C36 C33 109.8(11) . . ?
F7 C36 C33 106.9(5) . . ?

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
O2 S1 N1 C1 57.22(19) . . . . ?
O1 S1 N1 C1 -173.17(17) . . . . ?
C7 S1 N1 C1 -58.93(19) . . . . ?
O3 S2 N4 C24 177.58(17) . . . . ?
O4 S2 N4 C24 47.4(2) . . . . ?
C30 S2 N4 C24 -67.9(2) . . . . ?
O3 S2 C30 C35 -157.61(18) . . . . ?
O4 S2 C30 C35 -26.2(2) . . . . ?
N4 S2 C30 C35 89.76(19) . . . . ?
O3 S2 C30 C31 24.8(2) . . . . ?
O4 S2 C30 C31 156.15(17) . . . . ?
N4 S2 C30 C31 -87.86(19) . . . . ?
S1 N1 C1 C2 -44.8(3) . . . . ?
S1 N1 C1 C6 138.24(19) . . . . ?
C45 C44 C39 C38 -160.8(2) . . . . ?
C43 C44 C39 C38 21.3(3) . . . . ?
C45 C44 C39 C40 19.8(3) . . . . ?
C43 C44 C39 C40 -158.2(2) . . . . ?
C10 C11 C12 C7 0.4(3) . . . . ?
C12 C11 C10 C9 -1.1(3) . . . . ?
C12 C11 C10 C13 -179.0(2) . . . . ?
C35 C30 C31 C32 -0.7(3) . . . . ?
S2 C30 C31 C32 176.91(17) . . . . ?
C28 C29 C24 C25 -1.0(3) . . . . ?
C28 C29 C24 N4 174.6(2) . . . . ?
S2 N4 C24 C25 -46.7(3) . . . . ?
S2 N4 C24 C29 137.78(19) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C14 C15 C16 C21 -179.2(2) . . . . ?
C30 C31 C32 C33 -0.6(3) . . . . ?
C11 C10 C9 C8 1.0(3) . . . . ?
C13 C10 C9 C8 178.9(2) . . . . ?
C11 C12 C7 C8 0.3(3) . . . . ?
C11 C12 C7 S1 -177.41(17) . . . . ?
O2 S1 C7 C12 -15.2(2) . . . . ?
O1 S1 C7 C12 -146.13(18) . . . . ?
N1 S1 C7 C12 102.27(19) . . . . ?
O2 S1 C7 C8 167.03(17) . . . . ?
O1 S1 C7 C8 36.1(2) . . . . ?
N1 S1 C7 C8 -75.55(19) . . . . ?
C43 C44 C45 C46 1.3(3) . . . . ?
C39 C44 C45 C46 -176.8(2) . . . . ?
C40 C39 C38 C37 1.0(3) . . . . ?
C44 C39 C38 C37 -178.5(2) . . . . ?
C31 C30 C35 C34 1.0(3) . . . . ?
S2 C30 C35 C34 -176.58(18) . . . . ?
C17 C16 C21 C22 -20.5(3) . . . . ?
C15 C16 C21 C22 158.3(2) . . . . ?
C17 C16 C21 C20 159.3(2) . . . . ?
C15 C16 C21 C20 -22.0(3) . . . . ?
C20 C21 C22 C23 -0.3(3) . . . . ?
C16 C21 C22 C23 179.5(2) . . . . ?
C46 N6 C42 C43 0.8(4) . . . . ?
C15 C16 C17 C18 1.3(3) . . . . ?
C21 C16 C17 C18 -179.9(2) . . . . ?
C38 C39 C40 C41 -0.7(3) . . . . ?
C44 C39 C40 C41 178.8(2) . . . . ?
C41 N5 C37 C38 -0.8(4) . . . . ?
C39 C38 C37 N5 -0.3(4) . . . . ?
C22 C21 C20 C19 0.1(3) . . . . ?
C16 C21 C20 C19 -179.7(2) . . . . ?
C10 C9 C8 C7 -0.2(3) . . . . ?
C12 C7 C8 C9 -0.4(3) . . . . ?
S1 C7 C8 C9 177.38(17) . . . . ?
C18 N2 C14 C15 1.9(3) . . . . ?
C16 C15 C14 N2 -1.3(4) . . . . ?
C31 C32 C33 C34 1.6(3) . . . . ?
C31 C32 C33 C36 179.4(2) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
N1 C1 C6 C5 175.9(2) . . . . ?
C9 C10 C13 F1 -105.5(2) . . . . ?
C11 C10 C13 F1 72.5(3) . . . . ?
C9 C10 C13 F3 14.9(3) . . . . ?
C11 C10 C13 F3 -167.2(2) . . . . ?
C9 C10 C13 F2 135.2(2) . . . . ?
C11 C10 C13 F2 -46.9(3) . . . . ?
C19 N3 C23 C22 0.3(4) . . . . ?
C21 C22 C23 N3 0.1(4) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
N1 C1 C2 C3 -177.2(2) . . . . ?
N6 C42 C43 C44 -0.1(4) . . . . ?
C45 C44 C43 C42 -0.9(3) . . . . ?
C39 C44 C43 C42 177.2(2) . . . . ?
C14 N2 C18 C17 -0.8(3) . . . . ?
C16 C17 C18 N2 -0.7(4) . . . . ?
C32 C33 C34 C35 -1.3(4) . . . . ?
C36 C33 C34 C35 -179.1(2) . . . . ?
C30 C35 C34 C33 0.0(3) . . . . ?
C24 C29 C28 C27 2.2(4) . . . . ?
C29 C24 C25 C26 -0.9(3) . . . . ?
N4 C24 C25 C26 -176.3(2) . . . . ?
C23 N3 C19 C20 -0.5(4) . . . . ?
C21 C20 C19 N3 0.3(4) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
C29 C28 C27 C26 -1.4(4) . . . . ?
C24 C25 C26 C27 1.6(4) . . . . ?
C28 C27 C26 C25 -0.5(4) . . . . ?
C1 C6 C5 C4 1.7(4) . . . . ?
C42 N6 C46 C45 -0.4(4) . . . . ?
C44 C45 C46 N6 -0.7(4) . . . . ?
C37 N5 C41 C40 1.1(4) . . . . ?
C39 C40 C41 N5 -0.4(4) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C6 C5 C4 C3 -0.7(4) . . . . ?
C34 C33 C36 F8 51.1(16) . . . . ?
C32 C33 C36 F8 -126.7(16) . . . . ?
C34 C33 C36 F4 -148.7(4) . . . . ?
C32 C33 C36 F4 33.4(5) . . . . ?
C34 C33 C36 F5 -22.7(4) . . . . ?
C32 C33 C36 F5 159.4(3) . . . . ?
C34 C33 C36 F6 92.6(3) . . . . ?
C32 C33 C36 F6 -85.3(3) . . . . ?
C34 C33 C36 F9 -175.5(12) . . . . ?
C32 C33 C36 F9 6.6(12) . . . . ?
C34 C33 C36 F7 -75.2(10) . . . . ?
C32 C33 C36 F7 106.9(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 N2 . . . 2.940(3) 0.87(3) 2.07(3) 173(3) no
N4 H4 N5 . . . 2.920(3) 0.85(3) 2.08(3) 177(3) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_shh003_1a_s86a14N
_database_code_depnum_ccdc_archive 'CCDC 2087479'
loop_
_audit_author_name
_audit_author_address
'Misaki Okayasu'
;Toho University
Japan
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-10-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C88 H68 F3 N11 O6 S3'
_chemical_formula_moiety         'C88 H68 F3 N11 O6 S3'
_chemical_formula_weight         1528.75
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   15.7030(5)
_cell_length_b                   30.2596(8)
_cell_length_c                   17.0294(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 111.871(4)
_cell_angle_gamma                90.0000
_cell_volume                     7509.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    25981
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      29.47
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3184.00
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.762
_exptl_absorpt_correction_T_max  0.980

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            113014
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_av_R_equivalents  0.0763
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.520
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             17141
_reflns_number_gt                11645
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1367
_refine_ls_wR_factor_gt          0.1226
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         17141
_refine_ls_number_parameters     1212
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0611P)²+1.9489P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.59
_refine_diff_density_min         -0.62
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.70424(3) 0.18833(2) 0.01917(3) 0.02156(12) Uani 1 1 d . . . . .
S2 S 0.24682(3) 0.11838(2) 0.01051(3) 0.02099(12) Uani 1 1 d . . . . .
S3 S 0.26839(4) 0.46314(2) -0.00873(3) 0.02434(12) Uani 1 1 d . . . . .
F1 F 0.61282(11) 0.21412(5) -0.22693(9) 0.0582(4) Uani 1 1 d . . . . .
F2 F 0.35586(9) 0.07563(5) 0.24725(9) 0.0487(4) Uani 1 1 d . . . . .
F3 F 0.35975(9) 0.42369(4) 0.22401(8) 0.0435(3) Uani 1 1 d . . . . .
O1 O 0.64995(9) 0.17438(4) 0.06616(9) 0.0267(3) Uani 1 1 d . . . . .
O2 O 0.79917(9) 0.17566(4) 0.04768(9) 0.0286(3) Uani 1 1 d . . . . .
O3 O 0.28952(9) 0.14814(4) -0.02907(8) 0.0263(3) Uani 1 1 d . . . . .
O4 O 0.14839(9) 0.11692(5) -0.01840(9) 0.0288(3) Uani 1 1 d . . . . .
O5 O 0.31998(10) 0.48107(4) -0.05513(8) 0.0297(3) Uani 1 1 d . . . . .
O6 O 0.17204(10) 0.47277(5) -0.03594(9) 0.0323(4) Uani 1 1 d . . . . .
N1 N 0.65984(12) 0.16946(6) -0.07650(11) 0.0256(4) Uani 1 1 d . . . . .
H1 H 0.6982(15) 0.1683(7) -0.0976(14) 0.031 Uiso 1 1 d . U . . .
N2 N 0.28066(11) 0.12918(5) 0.11046(11) 0.0220(4) Uani 1 1 d . . . . .
H2 H 0.2432(15) 0.1204(7) 0.1288(13) 0.026 Uiso 1 1 d . U . . .
N3 N 0.31197(12) 0.48005(5) 0.08840(11) 0.0245(4) Uani 1 1 d . . . . .
H3A H 0.2717(15) 0.4783(7) 0.1120(14) 0.029 Uiso 1 1 d . U . . .
N4 N 0.8008(3) 0.34633(13) 0.3618(3) 0.0265(9) Uani 0.655(2) 1 d . . P A 1
N5 N 1.1086(7) 0.3555(3) 0.1460(7) 0.0368(16) Uani 0.655(2) 1 d . . P A 1
N6 N 0.8713(4) 0.22315(15) 0.3490(3) 0.0531(13) Uani 0.655(2) 1 d . . P A 1
N7 N 1.17397(15) 0.22648(7) 0.12046(16) 0.0470(5) Uani 1 1 d . . . . .
N8 N 1.14207(12) 0.10206(7) 0.16985(12) 0.0384(5) Uani 1 1 d . . . . .
N9 N 0.79971(14) 0.09860(7) 0.34975(14) 0.0468(6) Uani 1 1 d . . . . .
N10 N 1.17290(12) 0.47508(7) 0.15771(11) 0.0366(5) Uani 1 1 d . . . . .
N11 N 0.8538(3) 0.47501(12) 0.3626(3) 0.0444(10) Uani 0.655(2) 1 d . . P A 1
C1 C 0.56644(14) 0.17599(6) -0.12911(12) 0.0237(4) Uani 1 1 d . . . . .
C2 C 0.54384(17) 0.19722(8) -0.20609(14) 0.0369(6) Uani 1 1 d . . . . .
C3 C 0.45464(18) 0.20087(9) -0.26325(14) 0.0454(6) Uani 1 1 d . . . . .
H3 H 0.441568 0.215008 -0.316276 0.054 Uiso 1 1 calc R U . . .
C4 C 0.38454(16) 0.18351(8) -0.24181(14) 0.0385(6) Uani 1 1 d . . . . .
H4 H 0.322762 0.185256 -0.280584 0.046 Uiso 1 1 calc R U . . .
C5 C 0.40478(14) 0.16362(7) -0.16377(13) 0.0292(5) Uani 1 1 d . . . . .
H5 H 0.356493 0.152725 -0.148273 0.035 Uiso 1 1 calc R U . . .
C6 C 0.49490(13) 0.15949(6) -0.10810(13) 0.0233(4) Uani 1 1 d . . . . .
H6 H 0.508021 0.145273 -0.055132 0.028 Uiso 1 1 calc R U . . .
C7 C 0.69780(13) 0.24638(6) 0.01206(12) 0.0204(4) Uani 1 1 d . . . . .
C8 C 0.64367(13) 0.26864(6) 0.04571(12) 0.0234(4) Uani 1 1 d . . . . .
H8 H 0.608790 0.252851 0.071590 0.028 Uiso 1 1 calc R U . . .
C9 C 0.63981(14) 0.31566(6) 0.04177(12) 0.0248(4) Uani 1 1 d . . . . .
C10 C 0.69185(14) 0.33823(6) 0.00199(12) 0.0260(5) Uani 1 1 d . . . . .
C11 C 0.74558(14) 0.31378(7) -0.03339(12) 0.0262(5) Uani 1 1 d . . . . .
H11 H 0.779820 0.328955 -0.060702 0.031 Uiso 1 1 calc R U . . .
C12 C 0.74904(13) 0.26866(6) -0.02892(12) 0.0234(4) Uani 1 1 d . . . . .
H12 H 0.785249 0.252501 -0.052919 0.028 Uiso 1 1 calc R U . . .
C13 C 0.58490(16) 0.33976(7) 0.07639(13) 0.0322(5) Uani 1 1 d . . . . .
H13 H 0.548656 0.324582 0.101658 0.039 Uiso 1 1 calc R U . . .
C14 C 0.58405(17) 0.38500(7) 0.07342(13) 0.0395(6) Uani 1 1 d . . . . .
H14 H 0.547476 0.401079 0.097135 0.047 Uiso 1 1 calc R U . . .
C15 C 0.63690(17) 0.40790(7) 0.03553(13) 0.0378(6) Uani 1 1 d . . . . .
H15 H 0.636320 0.439291 0.034767 0.045 Uiso 1 1 calc R U . . .
C16 C 0.68891(16) 0.38555(7) -0.00007(13) 0.0335(5) Uani 1 1 d . . . . .
H16 H 0.723316 0.401421 -0.026331 0.040 Uiso 1 1 calc R U . . .
C17 C 0.37475(13) 0.13322(6) 0.16325(12) 0.0201(4) Uani 1 1 d . . . . .
C18 C 0.41205(14) 0.10580(7) 0.23250(13) 0.0273(5) Uani 1 1 d . . . . .
C19 C 0.50195(15) 0.10860(8) 0.28748(13) 0.0341(5) Uani 1 1 d . . . . .
H19 H 0.525016 0.089343 0.334787 0.041 Uiso 1 1 calc R U . . .
C20 C 0.55795(15) 0.13994(8) 0.27256(14) 0.0352(5) Uani 1 1 d . . . . .
H20 H 0.620400 0.142339 0.309445 0.042 Uiso 1 1 calc R U . . .
C21 C 0.52274(15) 0.16782(8) 0.20365(14) 0.0381(6) Uani 1 1 d . . . . .
H21 H 0.561498 0.189215 0.193165 0.046 Uiso 1 1 calc R U . . .
C22 C 0.43147(14) 0.16495(7) 0.14962(14) 0.0313(5) Uani 1 1 d . . . . .
H22 H 0.407818 0.184750 0.103223 0.038 Uiso 1 1 calc R U . . .
C23 C 0.28515(12) 0.06462(6) 0.00028(12) 0.0199(4) Uani 1 1 d . . . . .
C24 C 0.34156(13) 0.05818(6) -0.04358(12) 0.0217(4) Uani 1 1 d . . . . .
H24 H 0.363364 0.082840 -0.065151 0.026 Uiso 1 1 calc R U . . .
C25 C 0.36740(13) 0.01495(6) -0.05683(12) 0.0209(4) Uani 1 1 d . . . . .
C26 C 0.33426(13) -0.02151(6) -0.02378(12) 0.0244(4) Uani 1 1 d . . . . .
C27 C 0.27745(14) -0.01346(6) 0.02262(13) 0.0259(5) Uani 1 1 d . . . . .
H27 H 0.255928 -0.037642 0.045669 0.031 Uiso 1 1 calc R U . . .
C28 C 0.25314(13) 0.02865(6) 0.03472(13) 0.0250(4) Uani 1 1 d . . . . .
H28 H 0.215046 0.033707 0.066007 0.030 Uiso 1 1 calc R U . . .
C29 C 0.42460(13) 0.00693(7) -0.10289(12) 0.0252(4) Uani 1 1 d . . . . .
H29 H 0.447730 0.031117 -0.124500 0.030 Uiso 1 1 calc R U . . .
C30 C 0.44693(14) -0.03544(7) -0.11659(13) 0.0304(5) Uani 1 1 d . . . . .
H30 H 0.485014 -0.040441 -0.147905 0.036 Uiso 1 1 calc R U . . .
C31 C 0.41371(15) -0.07138(7) -0.08450(13) 0.0330(5) Uani 1 1 d . . . . .
H31 H 0.429119 -0.100614 -0.094685 0.040 Uiso 1 1 calc R U . . .
C32 C 0.35945(14) -0.06485(7) -0.03877(13) 0.0291(5) Uani 1 1 d . . . . .
H32 H 0.338340 -0.089564 -0.016748 0.035 Uiso 1 1 calc R U . . .
C33 C 0.40577(14) 0.47157(6) 0.13894(12) 0.0215(4) Uani 1 1 d . . . . .
C34 C 0.42914(15) 0.44346(6) 0.20775(13) 0.0269(5) Uani 1 1 d . . . . .
C35 C 0.51845(15) 0.43588(7) 0.26105(13) 0.0320(5) Uani 1 1 d . . . . .
H35 H 0.531717 0.416534 0.308048 0.038 Uiso 1 1 calc R U . . .
C36 C 0.58839(15) 0.45683(7) 0.24514(13) 0.0292(5) Uani 1 1 d . . . . .
H36 H 0.650434 0.452339 0.281591 0.035 Uiso 1 1 calc R U . . .
C37 C 0.56746(14) 0.48448(7) 0.17559(13) 0.0279(5) Uani 1 1 d . . . . .
H37 H 0.615551 0.498446 0.163771 0.033 Uiso 1 1 calc R U . . .
C38 C 0.47707(14) 0.49194(6) 0.12316(12) 0.0249(4) Uani 1 1 d . . . . .
H38 H 0.463704 0.511165 0.075979 0.030 Uiso 1 1 calc R U . . .
C39 C 0.28185(13) 0.40514(6) -0.00711(12) 0.0220(4) Uani 1 1 d . . . . .
C40 C 0.33504(13) 0.38635(6) -0.04606(12) 0.0228(4) Uani 1 1 d . . . . .
H40 H 0.365960 0.404491 -0.072490 0.027 Uiso 1 1 calc R U . . .
C41 C 0.34391(13) 0.33958(6) -0.04686(12) 0.0226(4) Uani 1 1 d . . . . .
C42 C 0.29750(13) 0.31342(6) -0.00602(12) 0.0227(4) Uani 1 1 d . . . . .
C43 C 0.24330(13) 0.33430(7) 0.03375(12) 0.0242(4) Uani 1 1 d . . . . .
H43 H 0.212103 0.316770 0.060836 0.029 Uiso 1 1 calc R U . . .
C44 C 0.23530(13) 0.37928(7) 0.03368(12) 0.0244(4) Uani 1 1 d . . . . .
H44 H 0.199016 0.393016 0.060610 0.029 Uiso 1 1 calc R U . . .
C45 C 0.39721(14) 0.31874(7) -0.08740(13) 0.0271(5) Uani 1 1 d . . . . .
H45 H 0.427420 0.336108 -0.115639 0.033 Uiso 1 1 calc R U . . .
C46 C 0.40539(15) 0.27383(7) -0.08610(13) 0.0293(5) Uani 1 1 d . . . . .
H46 H 0.441560 0.260100 -0.113160 0.035 Uiso 1 1 calc R U . . .
C47 C 0.36034(14) 0.24763(7) -0.04473(13) 0.0286(5) Uani 1 1 d . . . . .
H47 H 0.366853 0.216400 -0.044021 0.034 Uiso 1 1 calc R U . . .
C48 C 0.30753(14) 0.26656(7) -0.00572(12) 0.0269(5) Uani 1 1 d . . . . .
H48 H 0.277472 0.248487 0.021630 0.032 Uiso 1 1 calc R U . . .
C49 C 0.88286(17) 0.33850(8) 0.39592(15) 0.0376(6) Uani 1 1 d . . . . .
H49 H 0.903893 0.329496 0.453465 0.045 Uiso 0.655(2) 1 calc R U P A 1
H49A H 0.899298 0.342562 0.455064 0.045 Uiso 0.345(2) 1 calc R U P A 2
C50 C 0.94804(15) 0.34129(8) 0.36003(13) 0.0324(5) Uani 1 1 d . . . . .
H50 H 1.010586 0.335540 0.393457 0.039 Uiso 0.655(2) 1 calc R U P A 1
H50A H 1.010441 0.346543 0.394636 0.039 Uiso 0.345(2) 1 calc R U P A 2
C51 C 0.9240(2) 0.35203(14) 0.2786(2) 0.0214(8) Uani 0.655(2) 1 d . . P A 1
C52 C 0.8326(2) 0.36346(11) 0.23811(19) 0.0267(7) Uani 0.655(2) 1 d . . P A 1
H52 H 0.810358 0.373416 0.181107 0.032 Uiso 0.655(2) 1 calc R U P A 1
C53 C 0.7741(2) 0.36019(11) 0.2817(2) 0.0273(7) Uani 0.655(2) 1 d . . P A 1
H53 H 0.711588 0.368209 0.253236 0.033 Uiso 0.655(2) 1 calc R U P A 1
C54 C 1.1370(2) 0.36332(13) 0.2274(2) 0.0309(8) Uani 0.655(2) 1 d . . P A 1
H54 H 1.200161 0.369962 0.256416 0.037 Uiso 0.655(2) 1 calc R U P A 1
C55 C 1.0813(2) 0.36258(12) 0.2738(2) 0.0234(7) Uani 0.655(2) 1 d . . P A 1
H55 H 1.104011 0.371171 0.331661 0.028 Uiso 0.655(2) 1 calc R U P A 1
C56 C 0.98978(15) 0.34870(8) 0.23290(13) 0.0356(5) Uani 1 1 d . . . . .
C57 C 0.96288(17) 0.34659(8) 0.14756(14) 0.0393(6) Uani 1 1 d . . . . .
H57 H 0.899593 0.344007 0.113236 0.047 Uiso 1 1 calc R U . . .
C58 C 1.0274(2) 0.34818(10) 0.11063(18) 0.0557(8) Uani 1 1 d . . . . .
H58A H 1.007703 0.351974 0.051113 0.067 Uiso 0.345(2) 1 calc R U P A 2
H58 H 1.005957 0.343040 0.051379 0.067 Uiso 0.655(2) 1 calc R U P A 1
C59 C 0.9587(7) 0.2116(4) 0.3849(7) 0.057(3) Uani 0.655(2) 1 d . . P A 1
H59 H 0.980445 0.201872 0.442061 0.069 Uiso 0.655(2) 1 calc R U P A 1
C60 C 1.0208(4) 0.2129(2) 0.3441(4) 0.0485(16) Uani 0.655(2) 1 d . . P A 1
H60 H 1.083016 0.205898 0.376694 0.058 Uiso 0.655(2) 1 calc R U P A 1
C61 C 1.0005(2) 0.22272(8) 0.26567(16) 0.0482(7) Uani 1 1 d . . . . .
C62 C 0.8996(2) 0.23788(12) 0.2225(2) 0.0318(8) Uani 0.655(2) 1 d . . P A 1
H62 H 0.876515 0.247880 0.165558 0.038 Uiso 0.655(2) 1 calc R U P A 1
C63 C 0.8442(3) 0.23651(13) 0.2686(3) 0.0434(10) Uani 0.655(2) 1 d . . P A 1
H63 H 0.782295 0.245715 0.241469 0.052 Uiso 0.655(2) 1 calc R U P A 1
C64 C 1.2019(4) 0.23491(18) 0.2049(5) 0.0551(18) Uani 0.655(2) 1 d . . P A 1
H64 H 1.265257 0.240999 0.234029 0.066 Uiso 0.655(2) 1 calc R U P A 1
C65 C 1.1475(3) 0.23549(16) 0.2524(3) 0.0489(12) Uani 0.655(2) 1 d . . P A 1
H65 H 1.172100 0.244030 0.310199 0.059 Uiso 0.655(2) 1 calc R U P A 1
C66 C 1.06008(16) 0.22389(7) 0.21569(14) 0.0345(5) Uani 1 1 d . . . . .
C67 C 1.02608(18) 0.22143(11) 0.13080(16) 0.0559(8) Uani 1 1 d . . . . .
H67 H 0.961866 0.218458 0.100711 0.067 Uiso 1 1 calc R U . . .
C68 C 1.0848(2) 0.22324(13) 0.08752(18) 0.0760(11) Uani 1 1 d . . . . .
H68 H 1.057507 0.221995 0.027534 0.091 Uiso 1 1 calc R U . . .
C69 C 1.05539(15) 0.10240(9) 0.12461(15) 0.0473(7) Uani 1 1 d . . . . .
H69 H 1.037955 0.104149 0.064954 0.057 Uiso 1 1 calc R U . . .
C70 C 0.98599(15) 0.10045(9) 0.15565(15) 0.0464(7) Uani 1 1 d . . . . .
H70 H 0.923822 0.100365 0.117500 0.056 Uiso 1 1 calc R U . . .
C71 C 1.00546(14) 0.09868(7) 0.23936(13) 0.0306(5) Uani 1 1 d . . . . .
C72 C 1.0955(2) 0.11029(12) 0.2886(2) 0.0310(8) Uani 0.655(2) 1 d . . P A 1
H72 H 1.112321 0.116891 0.346957 0.037 Uiso 0.655(2) 1 calc R U P A 1
C73 C 1.1602(2) 0.11208(12) 0.2513(2) 0.0337(8) Uani 0.655(2) 1 d . . P A 1
H73 H 1.220816 0.120894 0.285356 0.040 Uiso 0.655(2) 1 calc R U P A 1
C74 C 0.7802(2) 0.11595(13) 0.2676(2) 0.0314(9) Uani 0.655(2) 1 d . . P A 1
H74 H 0.720735 0.127630 0.237390 0.038 Uiso 0.655(2) 1 calc R U P A 1
C75 C 0.8440(2) 0.11657(12) 0.2296(2) 0.0270(8) Uani 0.655(2) 1 d . . P A 1
H75 H 0.829754 0.128537 0.174589 0.032 Uiso 0.655(2) 1 calc R U P A 1
C76 C 0.93429(14) 0.09801(7) 0.27775(14) 0.0311(5) Uani 1 1 d . . . . .
C77 C 0.95496(16) 0.08897(8) 0.36052(15) 0.0407(6) Uani 1 1 d . . . . .
H77 H 1.016325 0.082137 0.396006 0.049 Uiso 1 1 calc R U . . .
C78 C 0.88646(18) 0.08965(9) 0.39373(16) 0.0468(7) Uani 1 1 d D . . . .
H78 H 0.903440 0.083220 0.452197 0.056 Uiso 1 1 calc R U . . .
C79 C 1.08524(15) 0.47166(8) 0.11442(13) 0.0340(5) Uani 1 1 d . . . . .
H79 H 1.065750 0.469892 0.054579 0.041 Uiso 1 1 calc R U . . .
C80 C 1.01860(14) 0.47041(7) 0.14879(13) 0.0314(5) Uani 1 1 d . . . . .
H80 H 0.955810 0.468010 0.112829 0.038 Uiso 1 1 calc R U . . .
C81 C 1.04229(14) 0.47258(8) 0.23358(14) 0.0357(6) Uani 1 1 d . . . . .
C82 C 1.13744(19) 0.48772(10) 0.28001(18) 0.0212(7) Uani 0.655(2) 1 d . . P A 1
H82 H 1.157076 0.496742 0.337471 0.025 Uiso 0.655(2) 1 calc R U P A 1
C83 C 1.1962(2) 0.48832(11) 0.23769(19) 0.0238(7) Uani 0.655(2) 1 d . . P A 1
H83 H 1.256985 0.498724 0.266808 0.029 Uiso 0.655(2) 1 calc R U P A 1
C84 C 0.9288(3) 0.46260(9) 0.3915(2) 0.0609(9) Uani 1 1 d . . . . .
H84 H 0.946661 0.450067 0.446445 0.073 Uiso 0.655(2) 1 calc R U P A 1
H84A H 0.944556 0.465659 0.450767 0.073 Uiso 0.345(2) 1 calc R U P A 2
C85 C 0.99606(19) 0.46340(8) 0.35759(16) 0.0453(6) Uani 1 1 d . . . . .
H85 H 1.058205 0.458123 0.392951 0.054 Uiso 1 1 calc R U . . .
C86 C 0.97414(16) 0.47160(9) 0.27483(16) 0.0457(7) Uani 1 1 d . . . . .
C87 C 0.8897(2) 0.49085(11) 0.2396(2) 0.0324(8) Uani 0.655(2) 1 d . . P A 1
H87 H 0.871011 0.504272 0.185312 0.039 Uiso 0.655(2) 1 calc R U P A 1
C88 C 0.8320(2) 0.49055(12) 0.2837(3) 0.0446(10) Uani 0.655(2) 1 d . . P A 1
H88 H 0.772029 0.502240 0.256176 0.054 Uiso 0.655(2) 1 calc R U P A 1
C87A C 0.8723(4) 0.45065(19) 0.2124(4) 0.0230(13) Uani 0.345(2) 1 d . . P A 2
H87A H 0.860996 0.440953 0.156301 0.028 Uiso 0.345(2) 1 calc R U P A 2
C88A C 0.8061(4) 0.4484(2) 0.2475(4) 0.0294(15) Uani 0.345(2) 1 d . . P A 2
H88A H 0.745309 0.440754 0.211760 0.035 Uiso 0.345(2) 1 calc R U P A 2
C53A C 0.7696(4) 0.3173(2) 0.2589(4) 0.0336(17) Uani 0.345(2) 1 d . . P A 2
H53A H 0.710476 0.306442 0.225207 0.040 Uiso 0.345(2) 1 calc R U P A 2
C52A C 0.8338(4) 0.3202(2) 0.2223(4) 0.0304(15) Uani 0.345(2) 1 d . . P A 2
H52A H 0.819078 0.311373 0.165218 0.037 Uiso 0.345(2) 1 calc R U P A 2
C55A C 1.0845(4) 0.3312(3) 0.2828(4) 0.0316(15) Uani 0.345(2) 1 d . . P A 2
H55A H 1.099472 0.319147 0.337819 0.038 Uiso 0.345(2) 1 calc R U P A 2
C54A C 1.1482(5) 0.3333(3) 0.2453(5) 0.0386(18) Uani 0.345(2) 1 d . . P A 2
H54A H 1.210033 0.326674 0.279688 0.046 Uiso 0.345(2) 1 calc R U P A 2
C82A C 1.1246(4) 0.4512(2) 0.2771(4) 0.0280(15) Uani 0.345(2) 1 d . . P A 2
H82A H 1.134740 0.435723 0.328329 0.034 Uiso 0.345(2) 1 calc R U P A 2
C83A C 1.1909(4) 0.4533(3) 0.2424(4) 0.0320(16) Uani 0.345(2) 1 d . . P A 2
H83A H 1.249594 0.440833 0.272410 0.038 Uiso 0.345(2) 1 calc R U P A 2
C75A C 0.8462(4) 0.0862(3) 0.2352(4) 0.0357(17) Uani 0.345(2) 1 d . . P A 2
H75A H 0.829276 0.077091 0.177938 0.043 Uiso 0.345(2) 1 calc R U P A 2
C74A C 0.7785(5) 0.0864(3) 0.2696(4) 0.053(2) Uani 0.345(2) 1 d D . P A 2
H74A H 0.717473 0.077849 0.236028 0.063 Uiso 0.345(2) 1 calc R U P A 2
C72A C 1.0952(4) 0.0742(2) 0.2839(3) 0.0230(13) Uani 0.345(2) 1 d . . P A 2
H72A H 1.106362 0.058314 0.334856 0.028 Uiso 0.345(2) 1 calc R U P A 2
C73A C 1.1594(4) 0.0763(2) 0.2468(4) 0.0257(14) Uani 0.345(2) 1 d . . P A 2
H73A H 1.215742 0.060836 0.271605 0.031 Uiso 0.345(2) 1 calc R U P A 2
C62A C 0.9250(5) 0.2080(2) 0.2446(4) 0.0333(16) Uani 0.345(2) 1 d . . P A 2
H62A H 0.896043 0.197038 0.188609 0.040 Uiso 0.345(2) 1 calc R U P A 2
C63A C 0.8769(5) 0.2062(3) 0.3003(5) 0.0403(18) Uani 0.345(2) 1 d . . P A 2
H63A H 0.812618 0.201024 0.277394 0.048 Uiso 0.345(2) 1 calc R U P A 2
N11A N 0.8232(4) 0.4564(2) 0.3292(4) 0.0259(14) Uani 0.345(2) 1 d . . P A 2
C89 C 1.1652(5) 0.2114(2) 0.2516(4) 0.0277(16) Uani 0.345(2) 1 d . . P A 2
H89 H 1.194658 0.201209 0.308034 0.033 Uiso 0.345(2) 1 calc R U P A 2
C90 C 1.2128(8) 0.2158(3) 0.1986(7) 0.034(2) Uani 0.345(2) 1 d . . P A 2
H90 H 1.277081 0.210666 0.220906 0.040 Uiso 0.345(2) 1 calc R U P A 2
C59A C 1.0077(7) 0.2199(3) 0.4121(6) 0.034(2) Uani 0.345(2) 1 d . . P A 2
H59A H 1.037637 0.224992 0.471152 0.041 Uiso 0.345(2) 1 calc R U P A 2
C60A C 1.0598(6) 0.2220(3) 0.3633(7) 0.029(2) Uani 0.345(2) 1 d . . P A 2
H60A H 1.124998 0.222938 0.386017 0.035 Uiso 0.345(2) 1 calc R U P A 2
N6A N 0.9185(9) 0.2114(6) 0.3833(14) 0.043(3) Uani 0.345(2) 1 d . . P A 2
N4A N 0.7849(5) 0.3289(3) 0.3396(5) 0.0254(16) Uani 0.345(2) 1 d . . P A 2
N5A N 1.1299(11) 0.3440(5) 0.1632(12) 0.037(3) Uani 0.345(2) 1 d . . P A 2
C51A C 0.9218(5) 0.3363(2) 0.2707(5) 0.0133(18) Uiso 0.345(2) 1 d . . P A 2


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.4331(14) . ?
S1 O2 1.4371(14) . ?
S1 N1 1.6186(17) . ?
S1 C7 1.7610(19) . ?
S2 O3 1.4323(14) . ?
S2 O4 1.4376(14) . ?
S2 N2 1.6163(17) . ?
S2 C23 1.7657(19) . ?
S3 O5 1.4324(15) . ?
S3 O6 1.4375(14) . ?
S3 N3 1.6196(18) . ?
S3 C39 1.767(2) . ?
F1 C2 1.359(3) . ?
F2 C18 1.357(2) . ?
F3 C34 1.359(2) . ?
N1 C1 1.419(3) . ?
N1 H1 0.81(2) . ?
N2 C17 1.420(2) . ?
N2 H2 0.81(2) . ?
N3 C33 1.425(3) . ?
N3 H3A 0.87(2) . ?
N4 C49 1.223(5) . ?
N4 C53 1.336(5) . ?
N5 C58 1.210(11) . ?
N5 C54 1.311(12) . ?
N6 C59 1.325(11) . ?
N6 C63 1.336(7) . ?
N7 C90 1.282(11) . ?
N7 C68 1.303(3) . ?
N7 C64 1.362(8) . ?
N8 C69 1.290(3) . ?
N8 C73 1.343(4) . ?
N8 C73A 1.460(6) . ?
N9 C78 1.315(3) . ?
N9 C74A 1.332(7) . ?
N9 C74 1.417(4) . ?
N10 C79 1.301(3) . ?
N10 C83 1.333(3) . ?
N10 C83A 1.512(7) . ?
N11 C84 1.157(5) . ?
N11 C88 1.342(6) . ?
C1 C2 1.382(3) . ?
C1 C6 1.393(3) . ?
C2 C3 1.381(3) . ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.367(3) . ?
C7 C12 1.417(3) . ?
C8 C9 1.425(3) . ?
C8 H8 0.9500 . ?
C9 C13 1.415(3) . ?
C9 C10 1.416(3) . ?
C10 C11 1.415(3) . ?
C10 C16 1.432(3) . ?
C11 C12 1.367(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.370(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.409(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.364(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.381(3) . ?
C17 C22 1.387(3) . ?
C18 C19 1.375(3) . ?
C19 C20 1.380(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.369(3) . ?
C23 C28 1.414(3) . ?
C24 C25 1.413(3) . ?
C24 H24 0.9500 . ?
C25 C29 1.416(3) . ?
C25 C26 1.422(3) . ?
C26 C27 1.416(3) . ?
C26 C32 1.420(3) . ?
C27 C28 1.368(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.372(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.402(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.366(3) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.382(3) . ?
C33 C38 1.389(3) . ?
C34 C35 1.377(3) . ?
C35 C36 1.379(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.386(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.385(3) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
C39 C40 1.369(3) . ?
C39 C44 1.417(3) . ?
C40 C41 1.423(3) . ?
C40 H40 0.9500 . ?
C41 C45 1.416(3) . ?
C41 C42 1.421(3) . ?
C42 C43 1.418(3) . ?
C42 C48 1.427(3) . ?
C43 C44 1.367(3) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
C45 C46 1.364(3) . ?
C45 H45 0.9500 . ?
C46 C47 1.413(3) . ?
C46 H46 0.9500 . ?
C47 C48 1.366(3) . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?
C49 C50 1.376(3) . ?
C49 N4A 1.508(7) . ?
C49 H49 0.9500 . ?
C49 H49A 0.9500 . ?
C50 C51 1.334(4) . ?
C50 C51A 1.428(8) . ?
C50 H50 0.9500 . ?
C50 H50A 0.9500 . ?
C51 C52 1.385(5) . ?
C51 C56 1.511(4) . ?
C52 C53 1.384(4) . ?
C52 H52 0.9500 . ?
C53 H53 0.9500 . ?
C54 C55 1.381(4) . ?
C54 H54 0.9500 . ?
C55 C56 1.407(4) . ?
C55 H55 0.9500 . ?
C56 C57 1.355(3) . ?
C56 C51A 1.486(8) . ?
C56 C55A 1.508(7) . ?
C57 C58 1.378(4) . ?
C57 H57 0.9500 . ?
C58 N5A 1.527(16) . ?
C58 H58A 0.9500 . ?
C58 H58 0.9500 . ?
C59 C60 1.393(11) . ?
C59 H59 0.9500 . ?
C60 C61 1.287(7) . ?
C60 H60 0.9500 . ?
C61 C62A 1.191(7) . ?
C61 C66 1.481(3) . ?
C61 C62 1.548(5) . ?
C61 C60A 1.575(10) . ?
C62 C63 1.371(5) . ?
C62 H62 0.9500 . ?
C63 H63 0.9500 . ?
C64 C65 1.377(9) . ?
C64 H64 0.9500 . ?
C65 C66 1.326(5) . ?
C65 H65 0.9500 . ?
C66 C67 1.344(3) . ?
C66 C89 1.577(8) . ?
C67 C68 1.380(4) . ?
C67 H67 0.9500 . ?
C68 H68 0.9500 . ?
C69 C70 1.378(3) . ?
C69 H69 0.9500 . ?
C70 C71 1.343(3) . ?
C70 H70 0.9500 . ?
C71 C72 1.394(4) . ?
C71 C76 1.490(3) . ?
C71 C72A 1.520(6) . ?
C72 C73 1.384(4) . ?
C72 H72 0.9500 . ?
C73 H73 0.9500 . ?
C74 C75 1.380(5) . ?
C74 H74 0.9500 . ?
C75 C76 1.461(4) . ?
C75 H75 0.9500 . ?
C76 C75A 1.349(7) . ?
C76 C77 1.352(3) . ?
C77 C78 1.389(3) . ?
C77 H77 0.9500 . ?
C78 H78 0.9500 . ?
C79 C80 1.377(3) . ?
C79 H79 0.9500 . ?
C80 C81 1.352(3) . ?
C80 H80 0.9500 . ?
C81 C82A 1.388(6) . ?
C81 C82 1.479(4) . ?
C81 C86 1.483(3) . ?
C82 C83 1.367(4) . ?
C82 H82 0.9500 . ?
C83 H83 0.9500 . ?
C84 C85 1.379(4) . ?
C84 N11A 1.612(7) . ?
C84 H84 0.9500 . ?
C84 H84A 0.9500 . ?
C85 C86 1.343(3) . ?
C85 H85 0.9500 . ?
C86 C87 1.366(4) . ?
C86 C87A 1.680(6) . ?
C87 C88 1.376(5) . ?
C87 H87 0.9500 . ?
C88 H88 0.9500 . ?
C87A C88A 1.381(8) . ?
C87A H87A 0.9500 . ?
C88A N11A 1.338(8) . ?
C88A H88A 0.9500 . ?
C53A N4A 1.351(9) . ?
C53A C52A 1.370(8) . ?
C53A H53A 0.9500 . ?
C52A C51A 1.407(9) . ?
C52A H52A 0.9500 . ?
C55A C54A 1.373(9) . ?
C55A H55A 0.9500 . ?
C54A N5A 1.36(2) . ?
C54A H54A 0.9500 . ?
C82A C83A 1.377(8) . ?
C82A H82A 0.9500 . ?
C83A H83A 0.9500 . ?
C75A C74A 1.392(10) . ?
C75A H75A 0.9500 . ?
C74A H74A 0.9500 . ?
C72A C73A 1.377(8) . ?
C72A H72A 0.9500 . ?
C73A H73A 0.9500 . ?
C62A C63A 1.416(10) . ?
C62A H62A 0.9500 . ?
C63A N6A 1.33(2) . ?
C63A H63A 0.9500 . ?
C89 C90 1.375(13) . ?
C89 H89 0.9500 . ?
C90 H90 0.9500 . ?
C59A N6A 1.325(18) . ?
C59A C60A 1.368(16) . ?
C59A H59A 0.9500 . ?
C60A H60A 0.9500 . ?

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 119.39(9) . . ?
O1 S1 N1 109.59(9) . . ?
O2 S1 N1 104.46(9) . . ?
O1 S1 C7 107.53(9) . . ?
O2 S1 C7 108.36(9) . . ?
N1 S1 C7 106.88(9) . . ?
O3 S2 O4 119.35(8) . . ?
O3 S2 N2 109.92(8) . . ?
O4 S2 N2 104.87(9) . . ?
O3 S2 C23 107.24(9) . . ?
O4 S2 C23 107.48(8) . . ?
N2 S2 C23 107.44(9) . . ?
O5 S3 O6 119.27(9) . . ?
O5 S3 N3 109.44(9) . . ?
O6 S3 N3 104.99(9) . . ?
O5 S3 C39 107.21(9) . . ?
O6 S3 C39 108.19(9) . . ?
N3 S3 C39 107.18(9) . . ?
C1 N1 S1 122.87(14) . . ?
C1 N1 H1 119.4(16) . . ?
S1 N1 H1 110.5(16) . . ?
C17 N2 S2 122.71(13) . . ?
C17 N2 H2 121.4(15) . . ?
S2 N2 H2 109.9(15) . . ?
C33 N3 S3 120.55(13) . . ?
C33 N3 H3A 118.5(14) . . ?
S3 N3 H3A 110.5(14) . . ?
C49 N4 C53 114.9(4) . . ?
C58 N5 C54 116.1(9) . . ?
C59 N6 C63 115.6(5) . . ?
C90 N7 C68 116.5(5) . . ?
C68 N7 C64 109.9(3) . . ?
C69 N8 C73 112.7(2) . . ?
C69 N8 C73A 110.0(3) . . ?
C78 N9 C74A 109.7(4) . . ?
C78 N9 C74 115.8(2) . . ?
C79 N10 C83 115.7(2) . . ?
C79 N10 C83A 106.8(3) . . ?
C84 N11 C88 112.3(4) . . ?
C2 C1 C6 117.63(19) . . ?
C2 C1 N1 120.23(18) . . ?
C6 C1 N1 122.06(18) . . ?
F1 C2 C3 118.9(2) . . ?
F1 C2 C1 118.3(2) . . ?
C3 C2 C1 122.7(2) . . ?
C2 C3 C4 118.7(2) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.54(19) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C8 C7 C12 121.86(18) . . ?
C8 C7 S1 119.46(15) . . ?
C12 C7 S1 118.68(15) . . ?
C7 C8 C9 119.66(19) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C13 C9 C10 120.04(19) . . ?
C13 C9 C8 121.13(19) . . ?
C10 C9 C8 118.83(18) . . ?
C11 C10 C9 119.57(18) . . ?
C11 C10 C16 122.1(2) . . ?
C9 C10 C16 118.34(19) . . ?
C12 C11 C10 121.07(19) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C7 118.98(19) . . ?
C11 C12 H12 120.5 . . ?
C7 C12 H12 120.5 . . ?
C14 C13 C9 119.9(2) . . ?
C14 C13 H13 120.0 . . ?
C9 C13 H13 120.0 . . ?
C13 C14 C15 120.6(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C10 120.2(2) . . ?
C15 C16 H16 119.9 . . ?
C10 C16 H16 119.9 . . ?
C18 C17 C22 117.66(18) . . ?
C18 C17 N2 119.93(17) . . ?
C22 C17 N2 122.38(18) . . ?
F2 C18 C19 119.26(19) . . ?
F2 C18 C17 117.66(18) . . ?
C19 C18 C17 123.1(2) . . ?
C18 C19 C20 118.7(2) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 H19 120.7 . . ?
C19 C20 C21 119.7(2) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C20 C21 C22 120.8(2) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C17 C22 C21 120.1(2) . . ?
C17 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C28 121.27(17) . . ?
C24 C23 S2 119.90(15) . . ?
C28 C23 S2 118.76(14) . . ?
C23 C24 C25 120.11(18) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C24 C25 C29 121.77(18) . . ?
C24 C25 C26 119.08(17) . . ?
C29 C25 C26 119.15(17) . . ?
C27 C26 C32 122.32(19) . . ?
C27 C26 C25 119.13(17) . . ?
C32 C26 C25 118.54(19) . . ?
C28 C27 C26 120.90(19) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C27 C28 C23 119.48(18) . . ?
C27 C28 H28 120.3 . . ?
C23 C28 H28 120.3 . . ?
C30 C29 C25 120.6(2) . . ?
C30 C29 H29 119.7 . . ?
C25 C29 H29 119.7 . . ?
C29 C30 C31 120.2(2) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C32 C31 C30 120.77(19) . . ?
C32 C31 H31 119.6 . . ?
C30 C31 H31 119.6 . . ?
C31 C32 C26 120.7(2) . . ?
C31 C32 H32 119.6 . . ?
C26 C32 H32 119.6 . . ?
C34 C33 C38 117.29(19) . . ?
C34 C33 N3 120.72(18) . . ?
C38 C33 N3 121.96(17) . . ?
F3 C34 C35 119.32(18) . . ?
F3 C34 C33 117.63(19) . . ?
C35 C34 C33 123.02(19) . . ?
C34 C35 C36 118.95(19) . . ?
C34 C35 H35 120.5 . . ?
C36 C35 H35 120.5 . . ?
C35 C36 C37 119.5(2) . . ?
C35 C36 H36 120.2 . . ?
C37 C36 H36 120.2 . . ?
C38 C37 C36 120.6(2) . . ?
C38 C37 H37 119.7 . . ?
C36 C37 H37 119.7 . . ?
C37 C38 C33 120.62(18) . . ?
C37 C38 H38 119.7 . . ?
C33 C38 H38 119.7 . . ?
C40 C39 C44 121.84(18) . . ?
C40 C39 S3 119.75(15) . . ?
C44 C39 S3 118.41(14) . . ?
C39 C40 C41 119.83(18) . . ?
C39 C40 H40 120.1 . . ?
C41 C40 H40 120.1 . . ?
C45 C41 C42 119.65(18) . . ?
C45 C41 C40 121.70(18) . . ?
C42 C41 C40 118.65(17) . . ?
C43 C42 C41 119.61(18) . . ?
C43 C42 C48 121.75(18) . . ?
C41 C42 C48 118.64(18) . . ?
C44 C43 C42 120.96(19) . . ?
C44 C43 H43 119.5 . . ?
C42 C43 H43 119.5 . . ?
C43 C44 C39 119.10(18) . . ?
C43 C44 H44 120.4 . . ?
C39 C44 H44 120.4 . . ?
C46 C45 C41 120.32(19) . . ?
C46 C45 H45 119.8 . . ?
C41 C45 H45 119.8 . . ?
C45 C46 C47 120.35(19) . . ?
C45 C46 H46 119.8 . . ?
C47 C46 H46 119.8 . . ?
C48 C47 C46 120.95(19) . . ?
C48 C47 H47 119.5 . . ?
C46 C47 H47 119.5 . . ?
C47 C48 C42 120.08(19) . . ?
C47 C48 H48 120.0 . . ?
C42 C48 H48 120.0 . . ?
N4 C49 C50 127.1(3) . . ?
C50 C49 N4A 118.7(3) . . ?
N4 C49 H49 116.4 . . ?
C50 C49 H49 116.4 . . ?
C50 C49 H49A 120.6 . . ?
N4A C49 H49A 120.6 . . ?
C51 C50 C49 120.5(3) . . ?
C49 C50 C51A 119.9(4) . . ?
C51 C50 H50 119.8 . . ?
C49 C50 H50 119.8 . . ?
C49 C50 H50A 120.0 . . ?
C51A C50 H50A 120.0 . . ?
C50 C51 C52 114.7(3) . . ?
C50 C51 C56 122.4(3) . . ?
C52 C51 C56 122.7(3) . . ?
C53 C52 C51 119.1(3) . . ?
C53 C52 H52 120.4 . . ?
C51 C52 H52 120.4 . . ?
N4 C53 C52 123.5(3) . . ?
N4 C53 H53 118.3 . . ?
C52 C53 H53 118.3 . . ?
N5 C54 C55 124.3(6) . . ?
N5 C54 H54 117.8 . . ?
C55 C54 H54 117.8 . . ?
C54 C55 C56 118.0(3) . . ?
C54 C55 H55 121.0 . . ?
C56 C55 H55 121.0 . . ?
C57 C56 C55 113.5(2) . . ?
C57 C56 C51A 117.7(3) . . ?
C57 C56 C55A 115.8(3) . . ?
C51A C56 C55A 112.6(4) . . ?
C57 C56 C51 123.8(2) . . ?
C55 C56 C51 119.5(2) . . ?
C56 C57 C58 119.9(2) . . ?
C56 C57 H57 120.0 . . ?
C58 C57 H57 120.0 . . ?
N5 C58 C57 126.6(6) . . ?
C57 C58 N5A 121.5(8) . . ?
C57 C58 H58A 119.2 . . ?
N5A C58 H58A 119.2 . . ?
N5 C58 H58 116.7 . . ?
C57 C58 H58 116.7 . . ?
N6 C59 C60 124.1(8) . . ?
N6 C59 H59 118.0 . . ?
C60 C59 H59 118.0 . . ?
C61 C60 C59 125.1(7) . . ?
C61 C60 H60 117.4 . . ?
C59 C60 H60 117.4 . . ?
C62A C61 C66 127.4(4) . . ?
C60 C61 C66 129.5(4) . . ?
C60 C61 C62 112.0(4) . . ?
C66 C61 C62 118.3(2) . . ?
C62A C61 C60A 116.3(5) . . ?
C66 C61 C60A 110.8(4) . . ?
C63 C62 C61 118.3(3) . . ?
C63 C62 H62 120.8 . . ?
C61 C62 H62 120.8 . . ?
N6 C63 C62 124.6(4) . . ?
N6 C63 H63 117.7 . . ?
C62 C63 H63 117.7 . . ?
N7 C64 C65 126.6(5) . . ?
N7 C64 H64 116.7 . . ?
C65 C64 H64 116.7 . . ?
C66 C65 C64 118.7(5) . . ?
C66 C65 H65 120.7 . . ?
C64 C65 H65 120.7 . . ?
C65 C66 C67 116.6(3) . . ?
C65 C66 C61 120.0(3) . . ?
C67 C66 C61 122.3(2) . . ?
C67 C66 C89 110.0(3) . . ?
C61 C66 C89 124.4(3) . . ?
C66 C67 C68 119.7(3) . . ?
C66 C67 H67 120.1 . . ?
C68 C67 H67 120.1 . . ?
N7 C68 C67 126.7(3) . . ?
N7 C68 H68 116.6 . . ?
C67 C68 H68 116.6 . . ?
N8 C69 C70 125.4(2) . . ?
N8 C69 H69 117.3 . . ?
C70 C69 H69 117.3 . . ?
C71 C70 C69 120.6(2) . . ?
C71 C70 H70 119.7 . . ?
C69 C70 H70 119.7 . . ?
C70 C71 C72 114.0(2) . . ?
C70 C71 C76 123.69(19) . . ?
C72 C71 C76 119.9(2) . . ?
C70 C71 C72A 110.6(3) . . ?
C76 C71 C72A 118.8(3) . . ?
C73 C72 C71 119.2(3) . . ?
C73 C72 H72 120.4 . . ?
C71 C72 H72 120.4 . . ?
N8 C73 C72 123.7(3) . . ?
N8 C73 H73 118.1 . . ?
C72 C73 H73 118.1 . . ?
C75 C74 N9 122.7(3) . . ?
C75 C74 H74 118.7 . . ?
N9 C74 H74 118.7 . . ?
C74 C75 C76 117.0(3) . . ?
C74 C75 H75 121.5 . . ?
C76 C75 H75 121.5 . . ?
C75A C76 C77 107.9(4) . . ?
C77 C76 C75 118.0(2) . . ?
C75A C76 C71 123.6(3) . . ?
C77 C76 C71 122.2(2) . . ?
C75 C76 C71 118.6(2) . . ?
C76 C77 C78 120.0(2) . . ?
C76 C77 H77 120.0 . . ?
C78 C77 H77 120.0 . . ?
N9 C78 C77 124.5(2) . . ?
N9 C78 H78 117.8 . . ?
C77 C78 H78 117.8 . . ?
N10 C79 C80 124.9(2) . . ?
N10 C79 H79 117.5 . . ?
C80 C79 H79 117.5 . . ?
C81 C80 C79 120.2(2) . . ?
C81 C80 H80 119.9 . . ?
C79 C80 H80 119.9 . . ?
C80 C81 C82A 112.2(3) . . ?
C80 C81 C82 114.0(2) . . ?
C80 C81 C86 123.0(2) . . ?
C82A C81 C86 115.5(3) . . ?
C82 C81 C86 121.1(2) . . ?
C83 C82 C81 117.9(3) . . ?
C83 C82 H82 121.0 . . ?
C81 C82 H82 121.0 . . ?
N10 C83 C82 123.5(3) . . ?
N10 C83 H83 118.3 . . ?
C82 C83 H83 118.3 . . ?
N11 C84 C85 129.2(4) . . ?
C85 C84 N11A 119.1(3) . . ?
N11 C84 H84 115.4 . . ?
C85 C84 H84 115.4 . . ?
C85 C84 H84A 120.4 . . ?
N11A C84 H84A 120.4 . . ?
C86 C85 C84 120.4(3) . . ?
C86 C85 H85 119.8 . . ?
C84 C85 H85 119.8 . . ?
C85 C86 C87 111.6(3) . . ?
C85 C86 C81 123.5(2) . . ?
C87 C86 C81 122.5(2) . . ?
C85 C86 C87A 114.0(3) . . ?
C81 C86 C87A 113.1(3) . . ?
C86 C87 C88 119.1(3) . . ?
C86 C87 H87 120.5 . . ?
C88 C87 H87 120.5 . . ?
N11 C88 C87 125.1(3) . . ?
N11 C88 H88 117.5 . . ?
C87 C88 H88 117.5 . . ?
C88A C87A C86 115.9(5) . . ?
C88A C87A H87A 122.0 . . ?
C86 C87A H87A 122.0 . . ?
N11A C88A C87A 123.4(6) . . ?
N11A C88A H88A 118.3 . . ?
C87A C88A H88A 118.3 . . ?
N4A C53A C52A 124.4(6) . . ?
N4A C53A H53A 117.8 . . ?
C52A C53A H53A 117.8 . . ?
C53A C52A C51A 118.9(6) . . ?
C53A C52A H52A 120.5 . . ?
C51A C52A H52A 120.5 . . ?
C54A C55A C56 117.3(6) . . ?
C54A C55A H55A 121.4 . . ?
C56 C55A H55A 121.4 . . ?
N5A C54A C55A 125.3(9) . . ?
N5A C54A H54A 117.4 . . ?
C55A C54A H54A 117.4 . . ?
C83A C82A C81 116.9(5) . . ?
C83A C82A H82A 121.6 . . ?
C81 C82A H82A 121.6 . . ?
C82A C83A N10 121.8(5) . . ?
C82A C83A H83A 119.1 . . ?
N10 C83A H83A 119.1 . . ?
C76 C75A C74A 124.3(5) . . ?
C76 C75A H75A 117.9 . . ?
C74A C75A H75A 117.9 . . ?
N9 C74A C75A 119.6(6) . . ?
N9 C74A H74A 120.2 . . ?
C75A C74A H74A 120.2 . . ?
C73A C72A C71 116.7(4) . . ?
C73A C72A H72A 121.6 . . ?
C71 C72A H72A 121.6 . . ?
C72A C73A N8 120.9(5) . . ?
C72A C73A H73A 119.6 . . ?
N8 C73A H73A 119.6 . . ?
C61 C62A C63A 122.2(6) . . ?
C61 C62A H62A 118.9 . . ?
C63A C62A H62A 118.9 . . ?
N6A C63A C62A 122.3(8) . . ?
N6A C63A H63A 118.8 . . ?
C62A C63A H63A 118.8 . . ?
C88A N11A C84 117.6(5) . . ?
C90 C89 C66 117.9(7) . . ?
C90 C89 H89 121.0 . . ?
C66 C89 H89 121.0 . . ?
N7 C90 C89 122.7(9) . . ?
N7 C90 H90 118.6 . . ?
C89 C90 H90 118.6 . . ?
N6A C59A C60A 124.9(12) . . ?
N6A C59A H59A 117.5 . . ?
C60A C59A H59A 117.5 . . ?
C59A C60A C61 112.9(7) . . ?
C59A C60A H60A 123.5 . . ?
C61 C60A H60A 123.5 . . ?
C59A N6A C63A 116.8(14) . . ?
C53A N4A C49 116.7(6) . . ?
C54A N5A C58 113.3(13) . . ?
C52A C51A C50 119.5(6) . . ?
C52A C51A C56 122.8(6) . . ?
C50 C51A C56 117.8(5) . . ?

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
O1 S1 N1 C1 52.81(18) . . . . ?
O2 S1 N1 C1 -178.17(16) . . . . ?
C7 S1 N1 C1 -63.44(18) . . . . ?
O3 S2 N2 C17 -50.85(17) . . . . ?
O4 S2 N2 C17 179.69(15) . . . . ?
C23 S2 N2 C17 65.53(17) . . . . ?
O5 S3 N3 C33 -57.40(17) . . . . ?
O6 S3 N3 C33 173.45(15) . . . . ?
C39 S3 N3 C33 58.55(17) . . . . ?
S1 N1 C1 C2 121.55(19) . . . . ?
S1 N1 C1 C6 -62.0(2) . . . . ?
C6 C1 C2 F1 178.99(18) . . . . ?
N1 C1 C2 F1 -4.4(3) . . . . ?
C6 C1 C2 C3 -2.8(3) . . . . ?
N1 C1 C2 C3 173.8(2) . . . . ?
F1 C2 C3 C4 179.9(2) . . . . ?
C1 C2 C3 C4 1.6(4) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C3 C4 C5 C6 -2.4(3) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
N1 C1 C6 C5 -175.19(17) . . . . ?
O1 S1 C7 C8 -2.69(18) . . . . ?
O2 S1 C7 C8 -133.02(15) . . . . ?
N1 S1 C7 C8 114.91(16) . . . . ?
O1 S1 C7 C12 177.53(14) . . . . ?
O2 S1 C7 C12 47.20(17) . . . . ?
N1 S1 C7 C12 -64.87(17) . . . . ?
C12 C7 C8 C9 -1.6(3) . . . . ?
S1 C7 C8 C9 178.62(14) . . . . ?
C7 C8 C9 C13 -179.64(18) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C13 C9 C10 C11 -179.18(18) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
C13 C9 C10 C16 1.6(3) . . . . ?
C8 C9 C10 C16 -178.74(17) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C16 C10 C11 C12 178.43(18) . . . . ?
C10 C11 C12 C7 -0.1(3) . . . . ?
C8 C7 C12 C11 1.3(3) . . . . ?
S1 C7 C12 C11 -178.90(14) . . . . ?
C10 C9 C13 C14 -1.8(3) . . . . ?
C8 C9 C13 C14 178.53(19) . . . . ?
C9 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C16 1.0(3) . . . . ?
C14 C15 C16 C10 -1.2(3) . . . . ?
C11 C10 C16 C15 -179.34(19) . . . . ?
C9 C10 C16 C15 -0.1(3) . . . . ?
S2 N2 C17 C18 -121.09(18) . . . . ?
S2 N2 C17 C22 60.9(2) . . . . ?
C22 C17 C18 F2 178.11(18) . . . . ?
N2 C17 C18 F2 0.0(3) . . . . ?
C22 C17 C18 C19 -0.2(3) . . . . ?
N2 C17 C18 C19 -178.34(19) . . . . ?
F2 C18 C19 C20 -178.91(19) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C18 C19 C20 C21 0.5(3) . . . . ?
C19 C20 C21 C22 0.5(3) . . . . ?
C18 C17 C22 C21 1.2(3) . . . . ?
N2 C17 C22 C21 179.29(19) . . . . ?
C20 C21 C22 C17 -1.4(3) . . . . ?
O3 S2 C23 C24 -3.07(18) . . . . ?
O4 S2 C23 C24 126.41(15) . . . . ?
N2 S2 C23 C24 -121.20(16) . . . . ?
O3 S2 C23 C28 179.77(14) . . . . ?
O4 S2 C23 C28 -50.75(17) . . . . ?
N2 S2 C23 C28 61.64(17) . . . . ?
C28 C23 C24 C25 1.4(3) . . . . ?
S2 C23 C24 C25 -175.73(14) . . . . ?
C23 C24 C25 C29 179.11(17) . . . . ?
C23 C24 C25 C26 -0.2(3) . . . . ?
C24 C25 C26 C27 -1.0(3) . . . . ?
C29 C25 C26 C27 179.69(18) . . . . ?
C24 C25 C26 C32 178.94(17) . . . . ?
C29 C25 C26 C32 -0.4(3) . . . . ?
C32 C26 C27 C28 -178.87(19) . . . . ?
C25 C26 C27 C28 1.0(3) . . . . ?
C26 C27 C28 C23 0.1(3) . . . . ?
C24 C23 C28 C27 -1.3(3) . . . . ?
S2 C23 C28 C27 175.82(15) . . . . ?
C24 C25 C29 C30 -178.44(18) . . . . ?
C26 C25 C29 C30 0.9(3) . . . . ?
C25 C29 C30 C31 -0.4(3) . . . . ?
C29 C30 C31 C32 -0.5(3) . . . . ?
C30 C31 C32 C26 1.0(3) . . . . ?
C27 C26 C32 C31 179.39(19) . . . . ?
C25 C26 C32 C31 -0.5(3) . . . . ?
S3 N3 C33 C34 -113.00(19) . . . . ?
S3 N3 C33 C38 69.0(2) . . . . ?
C38 C33 C34 F3 179.47(17) . . . . ?
N3 C33 C34 F3 1.4(3) . . . . ?
C38 C33 C34 C35 1.5(3) . . . . ?
N3 C33 C34 C35 -176.64(18) . . . . ?
F3 C34 C35 C36 -178.61(18) . . . . ?
C33 C34 C35 C36 -0.6(3) . . . . ?
C34 C35 C36 C37 -0.8(3) . . . . ?
C35 C36 C37 C38 1.4(3) . . . . ?
C36 C37 C38 C33 -0.5(3) . . . . ?
C34 C33 C38 C37 -0.9(3) . . . . ?
N3 C33 C38 C37 177.21(18) . . . . ?
O5 S3 C39 C40 0.34(19) . . . . ?
O6 S3 C39 C40 130.17(16) . . . . ?
N3 S3 C39 C40 -117.08(16) . . . . ?
O5 S3 C39 C44 -178.52(15) . . . . ?
O6 S3 C39 C44 -48.69(17) . . . . ?
N3 S3 C39 C44 64.05(17) . . . . ?
C44 C39 C40 C41 0.6(3) . . . . ?
S3 C39 C40 C41 -178.25(14) . . . . ?
C39 C40 C41 C45 179.13(18) . . . . ?
C39 C40 C41 C42 -0.6(3) . . . . ?
C45 C41 C42 C43 -179.30(18) . . . . ?
C40 C41 C42 C43 0.5(3) . . . . ?
C45 C41 C42 C48 1.2(3) . . . . ?
C40 C41 C42 C48 -179.06(17) . . . . ?
C41 C42 C43 C44 -0.3(3) . . . . ?
C48 C42 C43 C44 179.24(18) . . . . ?
C42 C43 C44 C39 0.2(3) . . . . ?
C40 C39 C44 C43 -0.4(3) . . . . ?
S3 C39 C44 C43 178.48(15) . . . . ?
C42 C41 C45 C46 -1.1(3) . . . . ?
C40 C41 C45 C46 179.12(19) . . . . ?
C41 C45 C46 C47 0.4(3) . . . . ?
C45 C46 C47 C48 0.3(3) . . . . ?
C46 C47 C48 C42 -0.3(3) . . . . ?
C43 C42 C48 C47 179.99(19) . . . . ?
C41 C42 C48 C47 -0.5(3) . . . . ?
C53 N4 C49 C50 -1.9(5) . . . . ?
N4 C49 C50 C51 -2.6(5) . . . . ?
N4A C49 C50 C51A 1.7(6) . . . . ?
C49 C50 C51 C52 5.4(5) . . . . ?
C49 C50 C51 C56 -170.3(3) . . . . ?
C50 C51 C52 C53 -4.1(5) . . . . ?
C56 C51 C52 C53 171.6(3) . . . . ?
C49 N4 C53 C52 3.2(5) . . . . ?
C51 C52 C53 N4 -0.2(5) . . . . ?
C58 N5 C54 C55 1.7(9) . . . . ?
N5 C54 C55 C56 5.9(7) . . . . ?
C54 C55 C56 C57 -13.1(4) . . . . ?
C54 C55 C56 C51 -173.5(3) . . . . ?
C50 C51 C56 C57 159.9(3) . . . . ?
C52 C51 C56 C57 -15.4(5) . . . . ?
C50 C51 C56 C55 -41.8(5) . . . . ?
C52 C51 C56 C55 142.8(3) . . . . ?
C55 C56 C57 C58 13.9(4) . . . . ?
C51A C56 C57 C58 -165.8(4) . . . . ?
C55A C56 C57 C58 -28.4(5) . . . . ?
C51 C56 C57 C58 173.3(3) . . . . ?
C54 N5 C58 C57 -1.2(9) . . . . ?
C56 C57 C58 N5 -7.3(6) . . . . ?
C56 C57 C58 N5A 11.1(7) . . . . ?
C63 N6 C59 C60 0.1(13) . . . . ?
N6 C59 C60 C61 -4.4(14) . . . . ?
C59 C60 C61 C66 -178.2(6) . . . . ?
C59 C60 C61 C62 5.8(9) . . . . ?
C60 C61 C62 C63 -3.9(5) . . . . ?
C66 C61 C62 C63 179.6(3) . . . . ?
C59 N6 C63 C62 1.5(9) . . . . ?
C61 C62 C63 N6 0.4(6) . . . . ?
C68 N7 C64 C65 6.5(7) . . . . ?
N7 C64 C65 C66 5.1(8) . . . . ?
C64 C65 C66 C67 -13.7(6) . . . . ?
C64 C65 C66 C61 178.0(4) . . . . ?
C60 C61 C66 C65 -33.3(6) . . . . ?
C62 C61 C66 C65 142.6(3) . . . . ?
C62A C61 C66 C67 22.4(6) . . . . ?
C60 C61 C66 C67 159.1(4) . . . . ?
C62 C61 C66 C67 -25.1(4) . . . . ?
C60A C61 C66 C67 175.1(5) . . . . ?
C62A C61 C66 C89 -135.2(6) . . . . ?
C60A C61 C66 C89 17.5(6) . . . . ?
C65 C66 C67 C68 11.1(5) . . . . ?
C61 C66 C67 C68 179.2(3) . . . . ?
C89 C66 C67 C68 -20.4(5) . . . . ?
C90 N7 C68 C67 19.1(7) . . . . ?
C64 N7 C68 C67 -9.5(5) . . . . ?
C66 C67 C68 N7 1.3(6) . . . . ?
C73 N8 C69 C70 -17.7(4) . . . . ?
C73A N8 C69 C70 31.0(5) . . . . ?
N8 C69 C70 C71 1.1(5) . . . . ?
C69 C70 C71 C72 15.6(4) . . . . ?
C69 C70 C71 C76 177.9(2) . . . . ?
C69 C70 C71 C72A -31.8(4) . . . . ?
C70 C71 C72 C73 -15.0(4) . . . . ?
C76 C71 C72 C73 -178.0(3) . . . . ?
C69 N8 C73 C72 17.8(5) . . . . ?
C71 C72 C73 N8 -1.8(5) . . . . ?
C78 N9 C74 C75 10.7(5) . . . . ?
N9 C74 C75 C76 0.5(5) . . . . ?
C74 C75 C76 C77 -11.7(4) . . . . ?
C74 C75 C76 C71 -179.1(3) . . . . ?
C70 C71 C76 C75A 20.3(6) . . . . ?
C72A C71 C76 C75A -127.7(6) . . . . ?
C70 C71 C76 C77 168.9(3) . . . . ?
C72 C71 C76 C77 -29.8(4) . . . . ?
C72A C71 C76 C77 20.9(4) . . . . ?
C70 C71 C76 C75 -24.2(4) . . . . ?
C72 C71 C76 C75 137.1(3) . . . . ?
C75A C76 C77 C78 -28.5(5) . . . . ?
C75 C76 C77 C78 11.7(4) . . . . ?
C71 C76 C77 C78 178.7(2) . . . . ?
C74A N9 C78 C77 29.4(6) . . . . ?
C74 N9 C78 C77 -11.4(4) . . . . ?
C76 C77 C78 N9 0.2(4) . . . . ?
C83 N10 C79 C80 -16.0(4) . . . . ?
C83A N10 C79 C80 29.9(4) . . . . ?
N10 C79 C80 C81 -0.3(4) . . . . ?
C79 C80 C81 C82A -35.1(4) . . . . ?
C79 C80 C81 C82 15.1(3) . . . . ?
C79 C80 C81 C86 179.7(2) . . . . ?
C80 C81 C82 C83 -14.2(4) . . . . ?
C86 C81 C82 C83 -179.1(3) . . . . ?
C79 N10 C83 C82 16.4(4) . . . . ?
C81 C82 C83 N10 -1.6(5) . . . . ?
C88 N11 C84 C85 2.7(6) . . . . ?
N11 C84 C85 C86 -13.9(5) . . . . ?
N11A C84 C85 C86 18.8(5) . . . . ?
C84 C85 C86 C87 18.0(4) . . . . ?
C84 C85 C86 C81 -179.4(2) . . . . ?
C84 C85 C86 C87A -35.4(4) . . . . ?
C80 C81 C86 C85 163.9(3) . . . . ?
C82A C81 C86 C85 19.8(5) . . . . ?
C82 C81 C86 C85 -32.5(4) . . . . ?
C80 C81 C86 C87 -35.3(4) . . . . ?
C82 C81 C86 C87 128.3(3) . . . . ?
C80 C81 C86 C87A 19.6(4) . . . . ?
C82A C81 C86 C87A -124.5(4) . . . . ?
C85 C86 C87 C88 -13.8(4) . . . . ?
C81 C86 C87 C88 -176.7(3) . . . . ?
C84 N11 C88 C87 1.9(6) . . . . ?
C86 C87 C88 N11 4.4(6) . . . . ?
C85 C86 C87A C88A 31.5(6) . . . . ?
C81 C86 C87A C88A 179.3(4) . . . . ?
C86 C87A C88A N11A -8.8(9) . . . . ?
N4A C53A C52A C51A -0.3(11) . . . . ?
C57 C56 C55A C54A 28.2(7) . . . . ?
C51A C56 C55A C54A 167.8(6) . . . . ?
C56 C55A C54A N5A -9.8(14) . . . . ?
C80 C81 C82A C83A 35.1(7) . . . . ?
C86 C81 C82A C83A -177.0(5) . . . . ?
C81 C82A C83A N10 -4.4(9) . . . . ?
C79 N10 C83A C82A -27.5(7) . . . . ?
C77 C76 C75A C74A 29.2(10) . . . . ?
C71 C76 C75A C74A -178.4(7) . . . . ?
C78 N9 C74A C75A -28.5(10) . . . . ?
C76 C75A C74A N9 -0.5(14) . . . . ?
C70 C71 C72A C73A 29.0(6) . . . . ?
C76 C71 C72A C73A -179.0(4) . . . . ?
C71 C72A C73A N8 1.8(8) . . . . ?
C69 N8 C73A C72A -30.9(7) . . . . ?
C66 C61 C62A C63A 175.8(5) . . . . ?
C60A C61 C62A C63A 24.4(10) . . . . ?
C61 C62A C63A N6A -15.2(16) . . . . ?
C87A C88A N11A C84 -8.3(9) . . . . ?
C85 C84 N11A C88A 5.7(7) . . . . ?
C67 C66 C89 C90 22.7(7) . . . . ?
C61 C66 C89 C90 -177.4(5) . . . . ?
C68 N7 C90 C89 -15.4(10) . . . . ?
C66 C89 C90 N7 -5.0(11) . . . . ?
N6A C59A C60A C61 11.6(19) . . . . ?
C62A C61 C60A C59A -22.6(10) . . . . ?
C66 C61 C60A C59A -178.6(7) . . . . ?
C60A C59A N6A C63A -3(3) . . . . ?
C62A C63A N6A C59A 2(2) . . . . ?
C52A C53A N4A C49 -10.1(11) . . . . ?
C50 C49 N4A C53A 9.2(8) . . . . ?
C55A C54A N5A C58 -7.4(16) . . . . ?
C57 C58 N5A C54A 7.7(14) . . . . ?
C53A C52A C51A C50 11.9(9) . . . . ?
C53A C52A C51A C56 -168.0(6) . . . . ?
C49 C50 C51A C52A -12.3(7) . . . . ?
C49 C50 C51A C56 167.6(4) . . . . ?
C57 C56 C51A C52A 3.9(8) . . . . ?
C55A C56 C51A C52A -134.8(6) . . . . ?
C57 C56 C51A C50 -176.0(4) . . . . ?
C55A C56 C51A C50 45.3(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 F1 . . . 2.743(2) 0.81(3) 2.52(2) 97.0(15) no
N1 H1 N4 . . 4_565 2.822(6) 0.81(3) 2.02(3) 168(2) no
N1 H1 N4A . . 4_565 2.827(10) 0.81(3) 2.02(3) 173(2) no
N2 H2 F2 . . . 2.720(2) 0.81(3) 2.525(19) 95.2(15) no
N2 H2 N8 . . 1_455 2.841(3) 0.81(3) 2.04(3) 176(2) no
N3 H3A F3 . . . 2.741(2) 0.87(3) 2.51(2) 95.9(14) no
N3 H3A N10 . . 1_455 2.847(3) 0.87(3) 1.98(3) 175.9(18) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


