# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_nca2_DMF2
_database_code_depnum_ccdc_archive 'CCDC 1935319'
loop_
_audit_author_name
_audit_author_address
'Suguru Ito'
;YOKOHAMA National University
Japan
;
_audit_update_record             
;
2019-06-20 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C32 H19 N5 S'
_chemical_formula_moiety         'C32 H19 N5 S'
_chemical_formula_weight         505.60
_chemical_melting_point          592.95-595.05

#==============================================================================
# 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                   9.71088(5)
_cell_length_b                   16.39216(9)
_cell_length_c                   15.37234(9)
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.2646(5)
_cell_angle_gamma                90.0000
_cell_volume                     2427.36(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16270
_cell_measurement_theta_min      3.97
_cell_measurement_theta_max      74.93
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.251
_exptl_crystal_size_min          0.133
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048.00
_exptl_absorpt_coefficient_mu    1.437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.654
_exptl_absorpt_correction_T_max  0.826

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

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            25682
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_theta_max         68.237
_diffrn_reflns_theta_min         3.959
_diffrn_reflns_theta_full        67.684
_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       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4448
_reflns_number_gt                4156
_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          0.0362
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0905
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4448
_refine_ls_number_parameters     343
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0459P)²+0.6105P] 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         0.16
_refine_diff_density_min         -0.33
_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 0.0181 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)
;
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 0.25453(4) 0.99002(3) 0.17780(3) 0.05486(13) Uani 1 1 d . . . . .
N1 N 0.16365(10) 0.82388(6) 0.44773(6) 0.0327(2) Uani 1 1 d . . . . .
N2 N 0.11036(10) 0.73114(7) 0.34144(7) 0.0360(2) Uani 1 1 d . . . . .
N3 N 0.21024(11) 0.92927(7) 0.25211(8) 0.0430(3) Uani 1 1 d . . . . .
N4 N 0.40532(12) 0.95538(7) 0.16457(8) 0.0425(3) Uani 1 1 d . . . . .
N5 N 0.89142(13) 0.85857(8) 0.07868(9) 0.0525(3) Uani 1 1 d . . . . .
C1 C 0.04147(12) 0.78647(7) 0.46464(8) 0.0330(3) Uani 1 1 d . . . . .
C2 C -0.04314(13) 0.79768(8) 0.53421(8) 0.0375(3) Uani 1 1 d . . . . .
C3 C -0.01232(16) 0.85317(9) 0.60364(9) 0.0463(3) Uani 1 1 d . . . . .
H3 H 0.0698 0.8841 0.6079 0.056 Uiso 1 1 calc R U . . .
C4 C -0.10243(18) 0.86240(11) 0.66554(10) 0.0574(4) Uani 1 1 d . . . . .
H4 H -0.0815 0.8997 0.7118 0.069 Uiso 1 1 calc R U . . .
C5 C -0.22363(17) 0.81696(12) 0.65976(11) 0.0609(5) Uani 1 1 d . . . . .
H5 H -0.2856 0.8246 0.7013 0.073 Uiso 1 1 calc R U . . .
C6 C -0.25356(16) 0.76115(11) 0.59395(11) 0.0545(4) Uani 1 1 d . . . . .
H6 H -0.3357 0.7305 0.5917 0.065 Uiso 1 1 calc R U . . .
C7 C -0.16461(13) 0.74822(9) 0.52921(9) 0.0431(3) Uani 1 1 d . . . . .
C8 C -0.19588(13) 0.68711(9) 0.46031(10) 0.0432(3) Uani 1 1 d . . . . .
C9 C -0.31185(15) 0.63422(10) 0.45623(12) 0.0560(4) Uani 1 1 d . . . . .
H9 H -0.3709 0.6373 0.5001 0.067 Uiso 1 1 calc R U . . .
C10 C -0.33993(16) 0.57865(10) 0.38975(14) 0.0644(5) Uani 1 1 d . . . . .
H10 H -0.4179 0.5445 0.3887 0.077 Uiso 1 1 calc R U . . .
C11 C -0.25457(16) 0.57204(10) 0.32368(14) 0.0613(5) Uani 1 1 d . . . . .
H11 H -0.2754 0.5343 0.2779 0.074 Uiso 1 1 calc R U . . .
C12 C -0.13945(15) 0.62136(9) 0.32624(11) 0.0496(4) Uani 1 1 d . . . . .
H12 H -0.0811 0.6168 0.2821 0.059 Uiso 1 1 calc R U . . .
C13 C -0.10843(13) 0.67817(8) 0.39380(9) 0.0395(3) Uani 1 1 d . . . . .
C14 C 0.01121(12) 0.73037(8) 0.39864(8) 0.0342(3) Uani 1 1 d . . . . .
C15 C 0.19886(12) 0.78792(8) 0.37296(8) 0.0326(3) Uani 1 1 d . . . . .
C16 C 0.32238(12) 0.81172(8) 0.33159(8) 0.0321(3) Uani 1 1 d . . . . .
C17 C 0.31646(12) 0.87705(8) 0.27021(8) 0.0316(3) Uani 1 1 d . . . . .
C18 C 0.42909(12) 0.89168(7) 0.21974(8) 0.0315(3) Uani 1 1 d . . . . .
C19 C 0.55120(12) 0.84214(7) 0.23179(8) 0.0317(3) Uani 1 1 d . . . . .
C20 C 0.55415(13) 0.78243(8) 0.29445(9) 0.0378(3) Uani 1 1 d . . . . .
H20 H 0.6342 0.7500 0.3057 0.045 Uiso 1 1 calc R U . . .
C21 C 0.44186(13) 0.76732(8) 0.34320(8) 0.0378(3) Uani 1 1 d . . . . .
H21 H 0.4503 0.7251 0.3850 0.045 Uiso 1 1 calc R U . . .
C22 C 0.66754(12) 0.85197(7) 0.17895(8) 0.0336(3) Uani 1 1 d . . . . .
C23 C 0.80333(14) 0.83515(9) 0.21541(10) 0.0429(3) Uani 1 1 d . . . . .
H23 H 0.8227 0.8212 0.2750 0.051 Uiso 1 1 calc R U . . .
C24 C 0.90900(15) 0.83913(10) 0.16360(11) 0.0505(4) Uani 1 1 d . . . . .
H24 H 0.9995 0.8273 0.1899 0.061 Uiso 1 1 calc R U . . .
C25 C 0.76175(16) 0.87589(9) 0.04489(10) 0.0469(3) Uani 1 1 d . . . . .
H25 H 0.7461 0.8903 -0.0147 0.056 Uiso 1 1 calc R U . . .
C26 C 0.64821(14) 0.87427(8) 0.09095(9) 0.0388(3) Uani 1 1 d . . . . .
H26 H 0.5594 0.8880 0.0632 0.047 Uiso 1 1 calc R U . . .
C27 C 0.24202(12) 0.88771(8) 0.49512(8) 0.0326(3) Uani 1 1 d . . . . .
C28 C 0.19912(15) 0.96767(9) 0.48307(9) 0.0454(3) Uani 1 1 d . . . . .
H28 H 0.1196 0.9804 0.4440 0.054 Uiso 1 1 calc R U . . .
C29 C 0.27419(18) 1.02872(9) 0.52902(11) 0.0554(4) Uani 1 1 d . . . . .
H29 H 0.2446 1.0832 0.5221 0.066 Uiso 1 1 calc R U . . .
C30 C 0.39201(18) 1.01032(10) 0.58489(10) 0.0543(4) Uani 1 1 d . . . . .
H30 H 0.4431 1.0523 0.6156 0.065 Uiso 1 1 calc R U . . .
C31 C 0.43530(16) 0.93074(10) 0.59590(10) 0.0537(4) Uani 1 1 d . . . . .
H31 H 0.5161 0.9184 0.6340 0.064 Uiso 1 1 calc R U . . .
C32 C 0.36007(15) 0.86858(9) 0.55098(9) 0.0445(3) Uani 1 1 d . . . . .
H32 H 0.3892 0.8141 0.5585 0.053 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# 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 N4 1.6072(12) . ?
S1 N3 1.6142(12) . ?
N1 C15 1.3729(15) . ?
N1 C1 1.3890(15) . ?
N1 C27 1.4369(16) . ?
N2 C15 1.3169(16) . ?
N2 C14 1.3836(15) . ?
N3 C17 1.3422(16) . ?
N4 C18 1.3466(17) . ?
N5 C25 1.331(2) . ?
N5 C24 1.334(2) . ?
C1 C14 1.3734(18) . ?
C1 C2 1.4403(16) . ?
C2 C3 1.406(2) . ?
C2 C7 1.425(2) . ?
C3 C4 1.3800(19) . ?
C3 H3 0.9400 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.368(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.4137(19) . ?
C6 H6 0.9400 . ?
C7 C8 1.462(2) . ?
C8 C9 1.416(2) . ?
C8 C13 1.4168(19) . ?
C9 C10 1.370(3) . ?
C9 H9 0.9400 . ?
C10 C11 1.394(3) . ?
C10 H10 0.9400 . ?
C11 C12 1.376(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.399(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.4373(18) . ?
C15 C16 1.4794(16) . ?
C16 C21 1.3621(17) . ?
C16 C17 1.4237(17) . ?
C17 C18 1.4389(16) . ?
C18 C19 1.4299(17) . ?
C19 C20 1.3710(18) . ?
C19 C22 1.4813(16) . ?
C20 C21 1.4209(17) . ?
C20 H20 0.9400 . ?
C21 H21 0.9400 . ?
C22 C26 1.3910(18) . ?
C22 C23 1.3936(18) . ?
C23 C24 1.3777(19) . ?
C23 H23 0.9400 . ?
C24 H24 0.9400 . ?
C25 C26 1.3839(18) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?
C27 C32 1.3787(18) . ?
C27 C28 1.3806(19) . ?
C28 C29 1.379(2) . ?
C28 H28 0.9400 . ?
C29 C30 1.374(2) . ?
C29 H29 0.9400 . ?
C30 C31 1.374(2) . ?
C30 H30 0.9400 . ?
C31 C32 1.386(2) . ?
C31 H31 0.9400 . ?
C32 H32 0.9400 . ?

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
N4 S1 N3 101.55(6) . . ?
C15 N1 C1 106.03(10) . . ?
C15 N1 C27 124.41(10) . . ?
C1 N1 C27 129.55(10) . . ?
C15 N2 C14 104.29(10) . . ?
C17 N3 S1 105.87(8) . . ?
C18 N4 S1 106.30(8) . . ?
C25 N5 C24 115.52(12) . . ?
C14 C1 N1 105.39(10) . . ?
C14 C1 C2 123.03(12) . . ?
N1 C1 C2 131.58(12) . . ?
C3 C2 C7 120.28(12) . . ?
C3 C2 C1 124.04(13) . . ?
C7 C2 C1 115.68(12) . . ?
C4 C3 C2 120.12(16) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.28(17) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.40(13) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 121.96(16) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C6 C7 C2 116.87(15) . . ?
C6 C7 C8 121.56(14) . . ?
C2 C7 C8 121.57(11) . . ?
C9 C8 C13 116.78(15) . . ?
C9 C8 C7 122.87(14) . . ?
C13 C8 C7 120.35(12) . . ?
C10 C9 C8 121.46(15) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 120.96(15) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 119.29(17) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 120.67(16) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 120.80(13) . . ?
C12 C13 C14 122.10(12) . . ?
C8 C13 C14 117.09(13) . . ?
C1 C14 N2 111.24(11) . . ?
C1 C14 C13 122.20(11) . . ?
N2 C14 C13 126.55(12) . . ?
N2 C15 N1 113.04(10) . . ?
N2 C15 C16 123.72(11) . . ?
N1 C15 C16 123.23(11) . . ?
C21 C16 C17 116.82(11) . . ?
C21 C16 C15 121.75(11) . . ?
C17 C16 C15 121.08(11) . . ?
N3 C17 C16 125.64(11) . . ?
N3 C17 C18 113.49(11) . . ?
C16 C17 C18 120.86(11) . . ?
N4 C18 C19 126.54(11) . . ?
N4 C18 C17 112.79(11) . . ?
C19 C18 C17 120.66(11) . . ?
C20 C19 C18 116.09(11) . . ?
C20 C19 C22 120.88(11) . . ?
C18 C19 C22 123.01(11) . . ?
C19 C20 C21 123.08(12) . . ?
C19 C20 H20 118.5 . . ?
C21 C20 H20 118.5 . . ?
C16 C21 C20 122.37(12) . . ?
C16 C21 H21 118.8 . . ?
C20 C21 H21 118.8 . . ?
C26 C22 C23 116.59(12) . . ?
C26 C22 C19 122.92(11) . . ?
C23 C22 C19 120.43(12) . . ?
C24 C23 C22 119.62(14) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
N5 C24 C23 124.38(14) . . ?
N5 C24 H24 117.8 . . ?
C23 C24 H24 117.8 . . ?
N5 C25 C26 124.89(14) . . ?
N5 C25 H25 117.6 . . ?
C26 C25 H25 117.6 . . ?
C25 C26 C22 118.97(13) . . ?
C25 C26 H26 120.5 . . ?
C22 C26 H26 120.5 . . ?
C32 C27 C28 120.83(13) . . ?
C32 C27 N1 119.70(12) . . ?
C28 C27 N1 119.46(11) . . ?
C29 C28 C27 119.29(13) . . ?
C29 C28 H28 120.4 . . ?
C27 C28 H28 120.4 . . ?
C30 C29 C28 120.35(14) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C31 C30 C29 120.17(15) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C32 120.18(14) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C27 C32 C31 119.17(13) . . ?
C27 C32 H32 120.4 . . ?
C31 C32 H32 120.4 . . ?

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
N4 S1 N3 C17 -0.10(11) . . . . ?
N3 S1 N4 C18 0.26(11) . . . . ?
C15 N1 C1 C14 -0.05(13) . . . . ?
C27 N1 C1 C14 179.43(11) . . . . ?
C15 N1 C1 C2 179.05(12) . . . . ?
C27 N1 C1 C2 -1.5(2) . . . . ?
C14 C1 C2 C3 178.28(12) . . . . ?
N1 C1 C2 C3 -0.7(2) . . . . ?
C14 C1 C2 C7 -1.91(17) . . . . ?
N1 C1 C2 C7 179.12(12) . . . . ?
C7 C2 C3 C4 -2.56(19) . . . . ?
C1 C2 C3 C4 177.24(12) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C3 C4 C5 C6 1.6(2) . . . . ?
C4 C5 C6 C7 -0.8(2) . . . . ?
C5 C6 C7 C2 -1.54(19) . . . . ?
C5 C6 C7 C8 178.57(13) . . . . ?
C3 C2 C7 C6 3.20(18) . . . . ?
C1 C2 C7 C6 -176.61(11) . . . . ?
C3 C2 C7 C8 -176.91(11) . . . . ?
C1 C2 C7 C8 3.27(17) . . . . ?
C6 C7 C8 C9 -3.45(19) . . . . ?
C2 C7 C8 C9 176.66(12) . . . . ?
C6 C7 C8 C13 176.93(12) . . . . ?
C2 C7 C8 C13 -2.95(18) . . . . ?
C13 C8 C9 C10 -1.7(2) . . . . ?
C7 C8 C9 C10 178.66(13) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 C12 0.9(2) . . . . ?
C10 C11 C12 C13 -0.6(2) . . . . ?
C11 C12 C13 C8 -1.0(2) . . . . ?
C11 C12 C13 C14 179.75(13) . . . . ?
C9 C8 C13 C12 2.08(19) . . . . ?
C7 C8 C13 C12 -178.29(12) . . . . ?
C9 C8 C13 C14 -178.63(11) . . . . ?
C7 C8 C13 C14 1.01(18) . . . . ?
N1 C1 C14 N2 0.29(14) . . . . ?
C2 C1 C14 N2 -178.91(11) . . . . ?
N1 C1 C14 C13 179.31(11) . . . . ?
C2 C1 C14 C13 0.11(19) . . . . ?
C15 N2 C14 C1 -0.42(14) . . . . ?
C15 N2 C14 C13 -179.38(12) . . . . ?
C12 C13 C14 C1 179.65(12) . . . . ?
C8 C13 C14 C1 0.37(18) . . . . ?
C12 C13 C14 N2 -1.5(2) . . . . ?
C8 C13 C14 N2 179.23(12) . . . . ?
C14 N2 C15 N1 0.39(14) . . . . ?
C14 N2 C15 C16 -178.67(11) . . . . ?
C1 N1 C15 N2 -0.22(14) . . . . ?
C27 N1 C15 N2 -179.74(11) . . . . ?
C1 N1 C15 C16 178.84(11) . . . . ?
C27 N1 C15 C16 -0.67(19) . . . . ?
N2 C15 C16 C21 -80.55(17) . . . . ?
N1 C15 C16 C21 100.49(15) . . . . ?
N2 C15 C16 C17 92.52(15) . . . . ?
N1 C15 C16 C17 -86.44(15) . . . . ?
S1 N3 C17 C16 -179.22(10) . . . . ?
S1 N3 C17 C18 -0.10(13) . . . . ?
C21 C16 C17 N3 -177.49(12) . . . . ?
C15 C16 C17 N3 9.11(19) . . . . ?
C21 C16 C17 C18 3.44(17) . . . . ?
C15 C16 C17 C18 -169.96(11) . . . . ?
S1 N4 C18 C19 -179.16(10) . . . . ?
S1 N4 C18 C17 -0.34(13) . . . . ?
N3 C17 C18 N4 0.30(16) . . . . ?
C16 C17 C18 N4 179.47(11) . . . . ?
N3 C17 C18 C19 179.20(11) . . . . ?
C16 C17 C18 C19 -1.63(17) . . . . ?
N4 C18 C19 C20 177.49(12) . . . . ?
C17 C18 C19 C20 -1.25(17) . . . . ?
N4 C18 C19 C22 -4.11(19) . . . . ?
C17 C18 C19 C22 177.16(11) . . . . ?
C18 C19 C20 C21 2.30(19) . . . . ?
C22 C19 C20 C21 -176.14(12) . . . . ?
C17 C16 C21 C20 -2.48(19) . . . . ?
C15 C16 C21 C20 170.87(12) . . . . ?
C19 C20 C21 C16 -0.4(2) . . . . ?
C20 C19 C22 C26 143.66(13) . . . . ?
C18 C19 C22 C26 -34.66(18) . . . . ?
C20 C19 C22 C23 -33.32(18) . . . . ?
C18 C19 C22 C23 148.36(13) . . . . ?
C26 C22 C23 C24 -1.7(2) . . . . ?
C19 C22 C23 C24 175.49(13) . . . . ?
C25 N5 C24 C23 1.0(2) . . . . ?
C22 C23 C24 N5 0.2(2) . . . . ?
C24 N5 C25 C26 -0.6(2) . . . . ?
N5 C25 C26 C22 -1.0(2) . . . . ?
C23 C22 C26 C25 2.04(19) . . . . ?
C19 C22 C26 C25 -175.05(12) . . . . ?
C15 N1 C27 C32 -79.40(16) . . . . ?
C1 N1 C27 C32 101.21(15) . . . . ?
C15 N1 C27 C28 99.63(15) . . . . ?
C1 N1 C27 C28 -79.76(17) . . . . ?
C32 C27 C28 C29 -1.3(2) . . . . ?
N1 C27 C28 C29 179.66(13) . . . . ?
C27 C28 C29 C30 1.3(2) . . . . ?
C28 C29 C30 C31 -0.5(3) . . . . ?
C29 C30 C31 C32 -0.2(3) . . . . ?
C28 C27 C32 C31 0.6(2) . . . . ?
N1 C27 C32 C31 179.59(12) . . . . ?
C30 C31 C32 C27 0.2(2) . . . . ?

#==============================================================================

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



#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/chloroform'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_nca2_with_NBA
_database_code_depnum_ccdc_archive 'CCDC 1935323'
loop_
_audit_author_name
_audit_author_address
'Suguru Ito'
;YOKOHAMA National University
Japan
;
_audit_update_record             
;
2019-06-20 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C39 H24 N6 O4 S'
_chemical_formula_moiety         'C39 H24 N6 O4 S'
_chemical_formula_weight         672.72
_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                   9.74862(8)
_cell_length_b                   17.91753(15)
_cell_length_c                   17.82303(15)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.1261(8)
_cell_angle_gamma                90.0000
_cell_volume                     3111.03(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22817
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      75.76
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.606
_exptl_crystal_size_mid          0.403
_exptl_crystal_size_min          0.319
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1392.00
_exptl_absorpt_coefficient_mu    1.382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.284
_exptl_absorpt_correction_T_max  0.643

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

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            36448
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_theta_max         68.249
_diffrn_reflns_theta_min         3.499
_diffrn_reflns_theta_full        67.684
_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       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_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             5700
_reflns_number_gt                5226
_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          0.0414
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1062
_refine_ls_wR_factor_gt          0.1042
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         5700
_refine_ls_number_parameters     455
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0568P)²+0.9914P] 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         0.21
_refine_diff_density_min         -0.38
_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 0.0181 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 0.32285(4) 0.19173(2) 0.21765(2) 0.04614(13) Uani 1 1 d . . . . .
O1 O 0.45754(15) 0.30363(7) 0.43246(8) 0.0597(4) Uani 1 1 d . . . . .
O2 O 0.49618(13) 0.41994(8) 0.45704(7) 0.0568(3) Uani 1 1 d . . . . .
O3 O 0.07747(13) 0.53661(7) 0.17069(7) 0.0513(3) Uani 1 1 d . . . . .
H1 H -0.002(3) 0.5536(16) 0.1337(16) 0.104(9) Uiso 1 1 d . . . . .
O4 O -0.03336(15) 0.42793(8) 0.16809(9) 0.0729(5) Uani 1 1 d . . . . .
N1 N 0.79484(12) 0.26377(7) 0.29239(6) 0.0333(3) Uani 1 1 d . . . . .
N2 N 0.71870(13) 0.37127(7) 0.34020(7) 0.0356(3) Uani 1 1 d . . . . .
N3 N 0.46690(14) 0.22396(7) 0.25053(7) 0.0411(3) Uani 1 1 d . . . . .
N4 N 0.28650(13) 0.24990(7) 0.15132(7) 0.0401(3) Uani 1 1 d . . . . .
N5 N 0.10656(14) 0.41894(8) -0.07163(8) 0.0443(3) Uani 1 1 d . . . . .
N6 N 0.44325(14) 0.37004(8) 0.41918(8) 0.0431(3) Uani 1 1 d . . . . .
C1 C 0.86939(14) 0.27564(8) 0.35968(8) 0.0315(3) Uani 1 1 d . . . . .
C2 C 0.98282(15) 0.23547(8) 0.39476(8) 0.0325(3) Uani 1 1 d . . . . .
C3 C 1.04667(17) 0.17312(9) 0.36362(9) 0.0403(3) Uani 1 1 d . . . . .
H3 H 1.0108 0.1526 0.3185 0.048 Uiso 1 1 calc R U . . .
C4 C 1.16135(18) 0.14154(10) 0.39837(10) 0.0461(4) Uani 1 1 d . . . . .
H4 H 1.2046 0.1007 0.3762 0.055 Uiso 1 1 calc R U . . .
C5 C 1.21294(18) 0.17013(10) 0.46620(10) 0.0461(4) Uani 1 1 d . . . . .
H5 H 1.2903 0.1481 0.4902 0.055 Uiso 1 1 calc R U . . .
C6 C 1.15135(16) 0.23019(9) 0.49806(9) 0.0410(4) Uani 1 1 d . . . . .
H6 H 1.1871 0.2484 0.5442 0.049 Uiso 1 1 calc R U . . .
C7 C 1.03614(15) 0.26565(8) 0.46406(8) 0.0335(3) Uani 1 1 d . . . . .
C8 C 0.97793(15) 0.33320(8) 0.49639(8) 0.0342(3) Uani 1 1 d . . . . .
C9 C 1.02753(16) 0.36324(10) 0.56540(9) 0.0412(4) Uani 1 1 d . . . . .
H9 H 1.0980 0.3383 0.5927 0.049 Uiso 1 1 calc R U . . .
C10 C 0.97500(18) 0.42800(10) 0.59330(9) 0.0475(4) Uani 1 1 d . . . . .
H10 H 1.0100 0.4470 0.6393 0.057 Uiso 1 1 calc R U . . .
C11 C 0.87011(18) 0.46603(10) 0.55422(10) 0.0471(4) Uani 1 1 d . . . . .
H11 H 0.8350 0.5106 0.5736 0.057 Uiso 1 1 calc R U . . .
C12 C 0.81830(16) 0.43810(9) 0.48738(9) 0.0412(4) Uani 1 1 d . . . . .
H12 H 0.7473 0.4636 0.4611 0.049 Uiso 1 1 calc R U . . .
C13 C 0.87028(15) 0.37200(8) 0.45798(8) 0.0334(3) Uani 1 1 d . . . . .
C14 C 0.81949(14) 0.34105(8) 0.38778(8) 0.0321(3) Uani 1 1 d . . . . .
C15 C 0.70735(15) 0.32366(8) 0.28434(8) 0.0339(3) Uani 1 1 d . . . . .
C16 C 0.60850(15) 0.33311(8) 0.22017(8) 0.0343(3) Uani 1 1 d . . . . .
C17 C 0.49444(15) 0.28429(8) 0.20870(8) 0.0341(3) Uani 1 1 d . . . . .
C18 C 0.39076(15) 0.29944(8) 0.15126(8) 0.0332(3) Uani 1 1 d . . . . .
C19 C 0.40127(15) 0.36294(8) 0.10329(8) 0.0330(3) Uani 1 1 d . . . . .
C20 C 0.51424(16) 0.40780(9) 0.11636(9) 0.0384(3) Uani 1 1 d . . . . .
H20 H 0.5248 0.4500 0.0857 0.046 Uiso 1 1 calc R U . . .
C21 C 0.61555(16) 0.39351(9) 0.17379(9) 0.0386(3) Uani 1 1 d . . . . .
H21 H 0.6898 0.4267 0.1801 0.046 Uiso 1 1 calc R U . . .
C22 C 0.29734(15) 0.38094(8) 0.04316(8) 0.0341(3) Uani 1 1 d . . . . .
C23 C 0.21962(16) 0.32677(9) 0.00501(9) 0.0379(3) Uani 1 1 d . . . . .
H23 H 0.2299 0.2761 0.0178 0.046 Uiso 1 1 calc R U . . .
C24 C 0.12730(17) 0.34807(9) -0.05177(9) 0.0430(4) Uani 1 1 d . . . . .
H24 H 0.0768 0.3108 -0.0776 0.052 Uiso 1 1 calc R U . . .
C25 C 0.18041(19) 0.47122(10) -0.03513(10) 0.0500(4) Uani 1 1 d . . . . .
H25 H 0.1668 0.5215 -0.0487 0.060 Uiso 1 1 calc R U . . .
C26 C 0.27537(18) 0.45480(9) 0.02131(10) 0.0458(4) Uani 1 1 d . . . . .
H26 H 0.3256 0.4934 0.0452 0.055 Uiso 1 1 calc R U . . .
C27 C 0.81977(15) 0.20875(8) 0.23555(8) 0.0342(3) Uani 1 1 d . . . . .
C28 C 0.77151(17) 0.13668(9) 0.24316(9) 0.0410(4) Uani 1 1 d . . . . .
H28 H 0.7173 0.1239 0.2838 0.049 Uiso 1 1 calc R U . . .
C29 C 0.80409(18) 0.08352(9) 0.19015(10) 0.0484(4) Uani 1 1 d . . . . .
H29 H 0.7734 0.0341 0.1950 0.058 Uiso 1 1 calc R U . . .
C30 C 0.88239(18) 0.10377(10) 0.12974(10) 0.0497(4) Uani 1 1 d . . . . .
H30 H 0.9037 0.0679 0.0935 0.060 Uiso 1 1 calc R U . . .
C31 C 0.92889(19) 0.17577(11) 0.12242(9) 0.0488(4) Uani 1 1 d . . . . .
H31 H 0.9821 0.1888 0.0815 0.059 Uiso 1 1 calc R U . . .
C32 C 0.89723(16) 0.22914(10) 0.17541(9) 0.0410(4) Uani 1 1 d . . . . .
H32 H 0.9280 0.2785 0.1705 0.049 Uiso 1 1 calc R U . . .
C33 C 0.35291(15) 0.39196(9) 0.35519(8) 0.0355(3) Uani 1 1 d . . . . .
C34 C 0.37526(17) 0.45914(9) 0.32100(10) 0.0441(4) Uani 1 1 d . . . . .
H34 H 0.4522 0.4883 0.3348 0.053 Uiso 1 1 calc R U . . .
C35 C 0.28253(17) 0.48295(9) 0.26592(9) 0.0419(4) Uani 1 1 d . . . . .
H35 H 0.2971 0.5284 0.2412 0.050 Uiso 1 1 calc R U . . .
C36 C 0.16774(15) 0.44018(8) 0.24674(8) 0.0358(3) Uani 1 1 d . . . . .
C37 C 0.15064(17) 0.37126(9) 0.28093(9) 0.0430(4) Uani 1 1 d . . . . .
H37 H 0.0746 0.3414 0.2670 0.052 Uiso 1 1 calc R U . . .
C38 C 0.24479(17) 0.34638(9) 0.33524(9) 0.0403(3) Uani 1 1 d . . . . .
H38 H 0.2349 0.2994 0.3579 0.048 Uiso 1 1 calc R U . . .
C40 C 0.06000(16) 0.46732(9) 0.19109(9) 0.0427(4) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# 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 N4 1.6058(13) . ?
S1 N3 1.6087(14) . ?
O1 N6 1.2201(19) . ?
O2 N6 1.2228(19) . ?
O3 C40 1.307(2) . ?
O3 H1 1.05(3) . ?
O4 C40 1.211(2) . ?
N1 C15 1.3748(19) . ?
N1 C1 1.3954(17) . ?
N1 C27 1.4407(18) . ?
N2 C15 1.3126(19) . ?
N2 C14 1.3842(17) . ?
N3 C17 1.346(2) . ?
N4 C18 1.349(2) . ?
N5 C24 1.332(2) . ?
N5 C25 1.336(2) . ?
N6 C33 1.4684(19) . ?
C1 C14 1.371(2) . ?
C1 C2 1.4423(19) . ?
C2 C3 1.403(2) . ?
C2 C7 1.428(2) . ?
C3 C4 1.379(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.366(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.408(2) . ?
C6 H6 0.9400 . ?
C7 C8 1.464(2) . ?
C8 C9 1.411(2) . ?
C8 C13 1.414(2) . ?
C9 C10 1.369(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.394(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.371(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.398(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.4395(19) . ?
C15 C16 1.4777(18) . ?
C16 C21 1.365(2) . ?
C16 C17 1.424(2) . ?
C17 C18 1.4376(19) . ?
C18 C19 1.429(2) . ?
C19 C20 1.376(2) . ?
C19 C22 1.4827(19) . ?
C20 C21 1.419(2) . ?
C20 H20 0.9400 . ?
C21 H21 0.9400 . ?
C22 C23 1.393(2) . ?
C22 C26 1.394(2) . ?
C23 C24 1.383(2) . ?
C23 H23 0.9400 . ?
C24 H24 0.9400 . ?
C25 C26 1.374(2) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?
C27 C28 1.383(2) . ?
C27 C32 1.383(2) . ?
C28 C29 1.387(2) . ?
C28 H28 0.9400 . ?
C29 C30 1.391(3) . ?
C29 H29 0.9400 . ?
C30 C31 1.375(3) . ?
C30 H30 0.9400 . ?
C31 C32 1.387(2) . ?
C31 H31 0.9400 . ?
C32 H32 0.9400 . ?
C33 C38 1.370(2) . ?
C33 C34 1.370(2) . ?
C34 C35 1.377(2) . ?
C34 H34 0.9400 . ?
C35 C36 1.389(2) . ?
C35 H35 0.9400 . ?
C36 C37 1.390(2) . ?
C36 C40 1.499(2) . ?
C37 C38 1.383(2) . ?
C37 H37 0.9400 . ?
C38 H38 0.9400 . ?

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
N4 S1 N3 101.59(7) . . ?
C40 O3 H1 110.4(16) . . ?
C15 N1 C1 105.79(11) . . ?
C15 N1 C27 125.51(11) . . ?
C1 N1 C27 127.78(12) . . ?
C15 N2 C14 104.38(12) . . ?
C17 N3 S1 106.02(10) . . ?
C18 N4 S1 106.37(10) . . ?
C24 N5 C25 117.74(13) . . ?
O1 N6 O2 124.28(14) . . ?
O1 N6 C33 118.20(14) . . ?
O2 N6 C33 117.49(14) . . ?
C14 C1 N1 105.29(12) . . ?
C14 C1 C2 123.03(12) . . ?
N1 C1 C2 131.53(13) . . ?
C3 C2 C7 119.39(13) . . ?
C3 C2 C1 124.76(13) . . ?
C7 C2 C1 115.75(13) . . ?
C4 C3 C2 120.87(15) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.03(16) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.10(15) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 122.17(15) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C6 C7 C2 117.41(14) . . ?
C6 C7 C8 121.22(13) . . ?
C2 C7 C8 121.29(13) . . ?
C9 C8 C13 117.28(14) . . ?
C9 C8 C7 122.21(13) . . ?
C13 C8 C7 120.49(13) . . ?
C10 C9 C8 121.26(15) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C9 C10 C11 120.68(15) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 119.71(16) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.53(15) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 120.52(13) . . ?
C12 C13 C14 122.31(13) . . ?
C8 C13 C14 117.16(13) . . ?
C1 C14 N2 111.35(12) . . ?
C1 C14 C13 122.11(13) . . ?
N2 C14 C13 126.54(13) . . ?
N2 C15 N1 113.18(12) . . ?
N2 C15 C16 123.14(13) . . ?
N1 C15 C16 123.67(13) . . ?
C21 C16 C17 117.18(13) . . ?
C21 C16 C15 120.90(13) . . ?
C17 C16 C15 121.61(13) . . ?
N3 C17 C16 125.79(13) . . ?
N3 C17 C18 113.38(13) . . ?
C16 C17 C18 120.73(13) . . ?
N4 C18 C19 126.50(13) . . ?
N4 C18 C17 112.64(13) . . ?
C19 C18 C17 120.81(13) . . ?
C20 C19 C18 116.00(13) . . ?
C20 C19 C22 121.09(13) . . ?
C18 C19 C22 122.91(13) . . ?
C19 C20 C21 123.22(14) . . ?
C19 C20 H20 118.4 . . ?
C21 C20 H20 118.4 . . ?
C16 C21 C20 122.04(14) . . ?
C16 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C23 C22 C26 116.75(13) . . ?
C23 C22 C19 123.10(13) . . ?
C26 C22 C19 120.15(13) . . ?
C24 C23 C22 119.50(14) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
N5 C24 C23 123.09(14) . . ?
N5 C24 H24 118.5 . . ?
C23 C24 H24 118.5 . . ?
N5 C25 C26 122.88(15) . . ?
N5 C25 H25 118.6 . . ?
C26 C25 H25 118.6 . . ?
C25 C26 C22 120.03(15) . . ?
C25 C26 H26 120.0 . . ?
C22 C26 H26 120.0 . . ?
C28 C27 C32 121.34(15) . . ?
C28 C27 N1 120.21(14) . . ?
C32 C27 N1 118.39(14) . . ?
C27 C28 C29 119.16(16) . . ?
C27 C28 H28 120.4 . . ?
C29 C28 H28 120.4 . . ?
C28 C29 C30 119.63(16) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
C31 C30 C29 120.70(16) . . ?
C31 C30 H30 119.6 . . ?
C29 C30 H30 119.6 . . ?
C30 C31 C32 119.99(17) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C27 C32 C31 119.17(16) . . ?
C27 C32 H32 120.4 . . ?
C31 C32 H32 120.4 . . ?
C38 C33 C34 122.81(14) . . ?
C38 C33 N6 118.40(14) . . ?
C34 C33 N6 118.67(14) . . ?
C33 C34 C35 118.56(15) . . ?
C33 C34 H34 120.7 . . ?
C35 C34 H34 120.7 . . ?
C34 C35 C36 120.40(15) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C35 C36 C37 119.42(14) . . ?
C35 C36 C40 121.50(14) . . ?
C37 C36 C40 119.07(14) . . ?
C38 C37 C36 120.40(14) . . ?
C38 C37 H37 119.8 . . ?
C36 C37 H37 119.8 . . ?
C33 C38 C37 118.27(14) . . ?
C33 C38 H38 120.9 . . ?
C37 C38 H38 120.9 . . ?
O4 C40 O3 124.30(15) . . ?
O4 C40 C36 122.30(15) . . ?
O3 C40 C36 113.40(13) . . ?

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
N4 S1 N3 C17 -0.37(12) . . . . ?
N3 S1 N4 C18 0.48(12) . . . . ?
C15 N1 C1 C14 1.07(16) . . . . ?
C27 N1 C1 C14 170.43(14) . . . . ?
C15 N1 C1 C2 -174.39(15) . . . . ?
C27 N1 C1 C2 -5.0(3) . . . . ?
C14 C1 C2 C3 -172.58(15) . . . . ?
N1 C1 C2 C3 2.2(3) . . . . ?
C14 C1 C2 C7 3.7(2) . . . . ?
N1 C1 C2 C7 178.44(15) . . . . ?
C7 C2 C3 C4 -1.1(2) . . . . ?
C1 C2 C3 C4 174.99(15) . . . . ?
C2 C3 C4 C5 1.8(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C5 C6 C7 C2 1.3(2) . . . . ?
C5 C6 C7 C8 -175.48(15) . . . . ?
C3 C2 C7 C6 -0.4(2) . . . . ?
C1 C2 C7 C6 -176.84(13) . . . . ?
C3 C2 C7 C8 176.38(14) . . . . ?
C1 C2 C7 C8 -0.1(2) . . . . ?
C6 C7 C8 C9 -4.5(2) . . . . ?
C2 C7 C8 C9 178.91(14) . . . . ?
C6 C7 C8 C13 174.15(14) . . . . ?
C2 C7 C8 C13 -2.5(2) . . . . ?
C13 C8 C9 C10 -1.1(2) . . . . ?
C7 C8 C9 C10 177.57(15) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C11 C12 C13 C8 -0.5(2) . . . . ?
C11 C12 C13 C14 -179.56(16) . . . . ?
C9 C8 C13 C12 1.2(2) . . . . ?
C7 C8 C13 C12 -177.47(14) . . . . ?
C9 C8 C13 C14 -179.73(14) . . . . ?
C7 C8 C13 C14 1.6(2) . . . . ?
N1 C1 C14 N2 -1.12(17) . . . . ?
C2 C1 C14 N2 174.83(13) . . . . ?
N1 C1 C14 C13 179.32(13) . . . . ?
C2 C1 C14 C13 -4.7(2) . . . . ?
C15 N2 C14 C1 0.70(17) . . . . ?
C15 N2 C14 C13 -179.77(15) . . . . ?
C12 C13 C14 C1 -179.04(15) . . . . ?
C8 C13 C14 C1 1.9(2) . . . . ?
C12 C13 C14 N2 1.5(2) . . . . ?
C8 C13 C14 N2 -177.58(14) . . . . ?
C14 N2 C15 N1 0.03(17) . . . . ?
C14 N2 C15 C16 178.96(14) . . . . ?
C1 N1 C15 N2 -0.71(18) . . . . ?
C27 N1 C15 N2 -170.38(14) . . . . ?
C1 N1 C15 C16 -179.63(14) . . . . ?
C27 N1 C15 C16 10.7(2) . . . . ?
N2 C15 C16 C21 61.6(2) . . . . ?
N1 C15 C16 C21 -119.55(17) . . . . ?
N2 C15 C16 C17 -111.82(18) . . . . ?
N1 C15 C16 C17 67.0(2) . . . . ?
S1 N3 C17 C16 176.45(13) . . . . ?
S1 N3 C17 C18 0.14(16) . . . . ?
C21 C16 C17 N3 -177.06(15) . . . . ?
C15 C16 C17 N3 -3.4(2) . . . . ?
C21 C16 C17 C18 -1.0(2) . . . . ?
C15 C16 C17 C18 172.69(13) . . . . ?
S1 N4 C18 C19 -177.95(13) . . . . ?
S1 N4 C18 C17 -0.44(16) . . . . ?
N3 C17 C18 N4 0.21(19) . . . . ?
C16 C17 C18 N4 -176.32(14) . . . . ?
N3 C17 C18 C19 177.87(13) . . . . ?
C16 C17 C18 C19 1.3(2) . . . . ?
N4 C18 C19 C20 176.65(15) . . . . ?
C17 C18 C19 C20 -0.7(2) . . . . ?
N4 C18 C19 C22 -2.8(2) . . . . ?
C17 C18 C19 C22 179.88(14) . . . . ?
C18 C19 C20 C21 -0.3(2) . . . . ?
C22 C19 C20 C21 179.16(15) . . . . ?
C17 C16 C21 C20 0.0(2) . . . . ?
C15 C16 C21 C20 -173.69(15) . . . . ?
C19 C20 C21 C16 0.6(3) . . . . ?
C20 C19 C22 C23 150.59(16) . . . . ?
C18 C19 C22 C23 -30.0(2) . . . . ?
C20 C19 C22 C26 -28.2(2) . . . . ?
C18 C19 C22 C26 151.25(16) . . . . ?
C26 C22 C23 C24 0.5(2) . . . . ?
C19 C22 C23 C24 -178.29(15) . . . . ?
C25 N5 C24 C23 0.9(3) . . . . ?
C22 C23 C24 N5 -1.1(3) . . . . ?
C24 N5 C25 C26 -0.1(3) . . . . ?
N5 C25 C26 C22 -0.5(3) . . . . ?
C23 C22 C26 C25 0.2(3) . . . . ?
C19 C22 C26 C25 179.08(16) . . . . ?
C15 N1 C27 C28 -109.50(17) . . . . ?
C1 N1 C27 C28 83.10(19) . . . . ?
C15 N1 C27 C32 73.05(19) . . . . ?
C1 N1 C27 C32 -94.35(18) . . . . ?
C32 C27 C28 C29 1.4(2) . . . . ?
N1 C27 C28 C29 -176.00(13) . . . . ?
C27 C28 C29 C30 -1.1(2) . . . . ?
C28 C29 C30 C31 0.6(2) . . . . ?
C29 C30 C31 C32 -0.3(3) . . . . ?
C28 C27 C32 C31 -1.1(2) . . . . ?
N1 C27 C32 C31 176.33(13) . . . . ?
C30 C31 C32 C27 0.5(2) . . . . ?
O1 N6 C33 C38 29.5(2) . . . . ?
O2 N6 C33 C38 -148.38(16) . . . . ?
O1 N6 C33 C34 -154.40(16) . . . . ?
O2 N6 C33 C34 27.7(2) . . . . ?
C38 C33 C34 C35 2.2(3) . . . . ?
N6 C33 C34 C35 -173.69(15) . . . . ?
C33 C34 C35 C36 1.2(3) . . . . ?
C34 C35 C36 C37 -3.2(3) . . . . ?
C34 C35 C36 C40 175.47(16) . . . . ?
C35 C36 C37 C38 2.0(3) . . . . ?
C40 C36 C37 C38 -176.77(16) . . . . ?
C34 C33 C38 C37 -3.4(3) . . . . ?
N6 C33 C38 C37 172.48(14) . . . . ?
C36 C37 C38 C33 1.3(3) . . . . ?
C35 C36 C40 O4 172.42(18) . . . . ?
C37 C36 C40 O4 -8.9(3) . . . . ?
C35 C36 C40 O3 -7.7(2) . . . . ?
C37 C36 C40 O3 171.03(16) . . . . ?

#==============================================================================
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
O3 H1 N5 . . 3_565 2.5952(18) 1.047 1.553 172.7 no

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



#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/chloroform'
####################################################################### 
# 
# 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_mix_CF3_BA
_database_code_depnum_ccdc_archive 'CCDC 1935321'
loop_
_audit_author_name
_audit_author_address
'Suguru Ito'
;YOKOHAMA National University
Japan
;
_audit_update_record             
;
2019-06-20 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT355_mix_CF3_BA          
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O1       - H1       .       1.12 Ang.
RESPONSE: This is due to the formation of an intermolecular hydrogen bond with pyridyl group.
;
# Added during the CSD deposition process: Thursday 20 June 2019 04:35 AM
# end Validation Reply Form


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

_chemical_formula_sum            'C40 H24 F3 N5 O2 S'
_chemical_formula_moiety         'C40 H24 F3 N5 O2 S'
_chemical_formula_weight         695.72
_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                   10.12758(5)
_cell_length_b                   16.68174(10)
_cell_length_c                   19.48203(10)
_cell_angle_alpha                90.0000
_cell_angle_beta                 99.0942(5)
_cell_angle_gamma                90.0000
_cell_volume                     3250.03(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22535
_cell_measurement_theta_min      4.61
_cell_measurement_theta_max      74.79
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.096
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1432.00
_exptl_absorpt_coefficient_mu    1.422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.721
_exptl_absorpt_correction_T_max  0.872

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

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            47694
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_theta_max         68.244
_diffrn_reflns_theta_min         4.597
_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       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_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             5949
_reflns_number_gt                5228
_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          0.0618
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1623
_refine_ls_wR_factor_gt          0.1580
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         5949
_refine_ls_number_parameters     464
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0836P)²+1.7274P] 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         0.66
_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 0.0181 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)
;
F F 0.0727 0.0534
;
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 0.67643(7) 0.17780(5) 0.26998(4) 0.0745(3) Uani 1 1 d . . . . .
F1 F 0.5317(4) 0.2904(2) 0.09000(14) 0.1750(16) Uani 1 1 d . . . . .
F2 F 0.5059(3) 0.4037(2) 0.05252(13) 0.1467(12) Uani 1 1 d . . . . .
F3 F 0.6610(2) 0.3356(2) 0.02534(10) 0.1460(13) Uani 1 1 d . . . . .
O1 O 0.91005(17) 0.53597(11) 0.34549(10) 0.0630(5) Uani 1 1 d . . . . .
H1 H 0.986(4) 0.561(2) 0.388(2) 0.109(12) Uiso 1 1 d . . . . .
O2 O 1.07806(19) 0.46420(15) 0.31790(12) 0.0872(7) Uani 1 1 d . . . . .
N1 N 0.19677(18) 0.24680(11) 0.19965(8) 0.0429(4) Uani 1 1 d . . . . .
N2 N 0.27351(18) 0.35721(11) 0.15377(9) 0.0466(4) Uani 1 1 d . . . . .
N3 N 0.5287(2) 0.20914(13) 0.23968(11) 0.0601(5) Uani 1 1 d . . . . .
N4 N 0.7191(2) 0.23903(13) 0.33359(12) 0.0614(6) Uani 1 1 d . . . . .
N5 N 0.9102(2) 0.41013(14) 0.55332(12) 0.0634(6) Uani 1 1 d . . . . .
C1 C 0.1218(2) 0.25592(12) 0.13355(10) 0.0408(4) Uani 1 1 d . . . . .
C2 C 0.0136(2) 0.20998(13) 0.09631(10) 0.0441(5) Uani 1 1 d . . . . .
C3 C -0.0433(2) 0.14173(15) 0.12228(13) 0.0538(6) Uani 1 1 d . . . . .
H3 H -0.0124 0.1247 0.1674 0.065 Uiso 1 1 calc R U . . .
C4 C -0.1437(3) 0.09978(17) 0.08214(14) 0.0612(6) Uani 1 1 d . . . . .
H4 H -0.1793 0.0542 0.0998 0.073 Uiso 1 1 calc R U . . .
C5 C -0.1921(3) 0.12566(17) 0.01483(14) 0.0611(6) Uani 1 1 d . . . . .
H5 H -0.2587 0.0966 -0.0128 0.073 Uiso 1 1 calc R U . . .
C6 C -0.1422(2) 0.19361(15) -0.01075(12) 0.0544(6) Uani 1 1 d . . . . .
H6 H -0.1782 0.2109 -0.0552 0.065 Uiso 1 1 calc R U . . .
C7 C -0.0380(2) 0.23845(13) 0.02794(11) 0.0451(5) Uani 1 1 d . . . . .
C8 C 0.0152(2) 0.31020(14) -0.00062(11) 0.0458(5) Uani 1 1 d . . . . .
C9 C -0.0361(3) 0.34063(16) -0.06732(12) 0.0564(6) Uani 1 1 d . . . . .
H9 H -0.1075 0.3147 -0.0943 0.068 Uiso 1 1 calc R U . . .
C10 C 0.0176(3) 0.40753(19) -0.09280(13) 0.0720(8) Uani 1 1 d . . . . .
H10 H -0.0172 0.4261 -0.1370 0.086 Uiso 1 1 calc R U . . .
C11 C 0.1232(3) 0.4480(2) -0.05363(15) 0.0774(9) Uani 1 1 d . . . . .
H11 H 0.1590 0.4932 -0.0716 0.093 Uiso 1 1 calc R U . . .
C12 C 0.1747(3) 0.42128(17) 0.01138(13) 0.0633(7) Uani 1 1 d . . . . .
H12 H 0.2452 0.4486 0.0377 0.076 Uiso 1 1 calc R U . . .
C13 C 0.1216(2) 0.35280(14) 0.03853(11) 0.0464(5) Uani 1 1 d . . . . .
C14 C 0.1723(2) 0.32327(13) 0.10691(10) 0.0429(5) Uani 1 1 d . . . . .
C15 C 0.2851(2) 0.30944(13) 0.20781(11) 0.0438(5) Uani 1 1 d . . . . .
C16 C 0.3888(2) 0.32069(13) 0.26960(11) 0.0442(5) Uani 1 1 d . . . . .
C17 C 0.5055(2) 0.27182(13) 0.27968(11) 0.0465(5) Uani 1 1 d . . . . .
C18 C 0.6150(2) 0.28908(13) 0.33402(11) 0.0466(5) Uani 1 1 d . . . . .
C19 C 0.6061(2) 0.35358(13) 0.38161(11) 0.0432(5) Uani 1 1 d . . . . .
C20 C 0.4919(2) 0.39873(14) 0.36922(11) 0.0461(5) Uani 1 1 d . . . . .
H20 H 0.4837 0.4419 0.3985 0.055 Uiso 1 1 calc R U . . .
C21 C 0.3853(2) 0.38339(14) 0.31421(11) 0.0467(5) Uani 1 1 d . . . . .
H21 H 0.3111 0.4170 0.3084 0.056 Uiso 1 1 calc R U . . .
C22 C 0.7127(2) 0.37135(13) 0.44079(11) 0.0458(5) Uani 1 1 d . . . . .
C23 C 0.6824(2) 0.40756(15) 0.49986(12) 0.0522(5) Uani 1 1 d . . . . .
H23 H 0.5939 0.4193 0.5034 0.063 Uiso 1 1 calc R U . . .
C24 C 0.7826(3) 0.42653(16) 0.55378(13) 0.0577(6) Uani 1 1 d . . . . .
H24 H 0.7593 0.4522 0.5925 0.069 Uiso 1 1 calc R U . . .
C25 C 0.9403(3) 0.3735(2) 0.49646(17) 0.0762(8) Uani 1 1 d . . . . .
H25 H 1.0293 0.3606 0.4954 0.091 Uiso 1 1 calc R U . . .
C26 C 0.8466(3) 0.35394(18) 0.43933(15) 0.0666(7) Uani 1 1 d . . . . .
H26 H 0.8726 0.3296 0.4007 0.080 Uiso 1 1 calc R U . . .
C27 C 0.1724(2) 0.19287(13) 0.25402(10) 0.0456(5) Uani 1 1 d . . . . .
C28 C 0.0922(3) 0.21802(17) 0.30078(12) 0.0606(6) Uani 1 1 d . . . . .
H28 H 0.0577 0.2698 0.2981 0.073 Uiso 1 1 calc R U . . .
C29 C 0.0630(3) 0.1661(2) 0.35182(14) 0.0735(8) Uani 1 1 d . . . . .
H29 H 0.0090 0.1827 0.3835 0.088 Uiso 1 1 calc R U . . .
C30 C 0.1148(3) 0.08970(19) 0.35512(14) 0.0709(8) Uani 1 1 d . . . . .
H30 H 0.0946 0.0545 0.3890 0.085 Uiso 1 1 calc R U . . .
C31 C 0.1958(3) 0.06464(16) 0.30901(14) 0.0658(7) Uani 1 1 d . . . . .
H31 H 0.2305 0.0129 0.3120 0.079 Uiso 1 1 calc R U . . .
C32 C 0.2261(3) 0.11666(14) 0.25766(12) 0.0539(6) Uani 1 1 d . . . . .
H32 H 0.2814 0.1003 0.2265 0.065 Uiso 1 1 calc R U . . .
C33 C 0.6912(3) 0.38312(16) 0.13946(12) 0.0543(6) Uani 1 1 d . . . . .
C34 C 0.8269(3) 0.36881(17) 0.14653(13) 0.0622(7) Uani 1 1 d . . . . .
H34 H 0.8607 0.3375 0.1138 0.075 Uiso 1 1 calc R U . . .
C35 C 0.9128(3) 0.40064(16) 0.20185(13) 0.0575(6) Uani 1 1 d . . . . .
H35 H 1.0041 0.3905 0.2064 0.069 Uiso 1 1 calc R U . . .
C36 C 0.8636(2) 0.44755(13) 0.25053(11) 0.0467(5) Uani 1 1 d . . . . .
C37 C 0.7267(2) 0.46186(15) 0.24331(12) 0.0507(5) Uani 1 1 d . . . . .
H37 H 0.6928 0.4937 0.2756 0.061 Uiso 1 1 calc R U . . .
C38 C 0.6409(2) 0.42894(16) 0.18843(12) 0.0545(6) Uani 1 1 d . . . . .
H38 H 0.5493 0.4376 0.1844 0.065 Uiso 1 1 calc R U . . .
C39 C 0.6002(3) 0.3520(2) 0.07748(15) 0.0748(8) Uani 1 1 d . . . . .
C40 C 0.9609(2) 0.48300(15) 0.30805(12) 0.0529(5) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# 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 N3 1.607(2) . ?
S1 N4 1.611(2) . ?
F1 C39 1.284(4) . ?
F2 C39 1.322(4) . ?
F3 C39 1.297(4) . ?
O1 C40 1.303(3) . ?
O1 H1 1.11(4) . ?
O2 C40 1.213(3) . ?
N1 C15 1.368(3) . ?
N1 C1 1.396(2) . ?
N1 C27 1.440(3) . ?
N2 C15 1.311(3) . ?
N2 C14 1.382(3) . ?
N3 C17 1.347(3) . ?
N4 C18 1.345(3) . ?
N5 C24 1.322(3) . ?
N5 C25 1.342(4) . ?
C1 C14 1.370(3) . ?
C1 C2 1.436(3) . ?
C2 C3 1.406(3) . ?
C2 C7 1.433(3) . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.411(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.458(3) . ?
C8 C13 1.410(3) . ?
C8 C9 1.415(3) . ?
C9 C10 1.369(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.387(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.401(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.437(3) . ?
C15 C16 1.479(3) . ?
C16 C21 1.364(3) . ?
C16 C17 1.423(3) . ?
C17 C18 1.437(3) . ?
C18 C19 1.433(3) . ?
C19 C20 1.369(3) . ?
C19 C22 1.479(3) . ?
C20 C21 1.419(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.377(3) . ?
C22 C26 1.391(3) . ?
C23 C24 1.377(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.383(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.378(3) . ?
C27 C32 1.380(3) . ?
C28 C29 1.386(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.375(4) . ?
C29 H29 0.9300 . ?
C30 C31 1.374(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.394(4) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 C38 1.381(3) . ?
C33 C34 1.381(4) . ?
C33 C39 1.492(4) . ?
C34 C35 1.380(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.382(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.393(3) . ?
C36 C40 1.492(3) . ?
C37 C38 1.380(3) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N3 S1 N4 101.37(11) . . ?
C40 O1 H1 112(2) . . ?
C15 N1 C1 105.91(17) . . ?
C15 N1 C27 125.21(17) . . ?
C1 N1 C27 127.94(18) . . ?
C15 N2 C14 104.13(18) . . ?
C17 N3 S1 106.12(15) . . ?
C18 N4 S1 106.46(16) . . ?
C24 N5 C25 116.7(2) . . ?
C14 C1 N1 104.94(18) . . ?
C14 C1 C2 123.14(18) . . ?
N1 C1 C2 131.91(19) . . ?
C3 C2 C7 119.5(2) . . ?
C3 C2 C1 125.02(19) . . ?
C7 C2 C1 115.46(19) . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 122.2(2) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C6 C7 C2 117.0(2) . . ?
C6 C7 C8 121.4(2) . . ?
C2 C7 C8 121.61(19) . . ?
C13 C8 C9 117.0(2) . . ?
C13 C8 C7 120.27(19) . . ?
C9 C8 C7 122.7(2) . . ?
C10 C9 C8 121.1(2) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 120.9(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.8(2) . . ?
C12 C13 C14 121.8(2) . . ?
C8 C13 C14 117.3(2) . . ?
C1 C14 N2 111.60(18) . . ?
C1 C14 C13 122.18(19) . . ?
N2 C14 C13 126.2(2) . . ?
N2 C15 N1 113.41(18) . . ?
N2 C15 C16 122.6(2) . . ?
N1 C15 C16 123.95(18) . . ?
C21 C16 C17 117.11(19) . . ?
C21 C16 C15 121.97(19) . . ?
C17 C16 C15 120.45(19) . . ?
N3 C17 C16 125.6(2) . . ?
N3 C17 C18 113.4(2) . . ?
C16 C17 C18 121.0(2) . . ?
N4 C18 C19 126.9(2) . . ?
N4 C18 C17 112.7(2) . . ?
C19 C18 C17 120.47(19) . . ?
C20 C19 C18 115.91(19) . . ?
C20 C19 C22 121.3(2) . . ?
C18 C19 C22 122.81(19) . . ?
C19 C20 C21 123.7(2) . . ?
C19 C20 H20 118.2 . . ?
C21 C20 H20 118.2 . . ?
C16 C21 C20 121.8(2) . . ?
C16 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C23 C22 C26 117.1(2) . . ?
C23 C22 C19 120.5(2) . . ?
C26 C22 C19 122.4(2) . . ?
C22 C23 C24 120.3(2) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
N5 C24 C23 123.4(2) . . ?
N5 C24 H24 118.3 . . ?
C23 C24 H24 118.3 . . ?
N5 C25 C26 123.7(3) . . ?
N5 C25 H25 118.1 . . ?
C26 C25 H25 118.1 . . ?
C25 C26 C22 118.8(3) . . ?
C25 C26 H26 120.6 . . ?
C22 C26 H26 120.6 . . ?
C28 C27 C32 121.0(2) . . ?
C28 C27 N1 118.9(2) . . ?
C32 C27 N1 120.1(2) . . ?
C27 C28 C29 119.9(3) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C30 C29 C28 119.3(3) . . ?
C30 C29 H29 120.3 . . ?
C28 C29 H29 120.3 . . ?
C31 C30 C29 120.9(3) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C30 C31 C32 120.1(3) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C27 C32 C31 118.7(2) . . ?
C27 C32 H32 120.6 . . ?
C31 C32 H32 120.6 . . ?
C38 C33 C34 119.8(2) . . ?
C38 C33 C39 120.3(2) . . ?
C34 C33 C39 119.9(2) . . ?
C35 C34 C33 120.4(2) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C34 C35 C36 120.2(2) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C35 C36 C37 119.3(2) . . ?
C35 C36 C40 118.2(2) . . ?
C37 C36 C40 122.5(2) . . ?
C38 C37 C36 120.3(2) . . ?
C38 C37 H37 119.8 . . ?
C36 C37 H37 119.8 . . ?
C37 C38 C33 120.0(2) . . ?
C37 C38 H38 120.0 . . ?
C33 C38 H38 120.0 . . ?
F1 C39 F3 108.5(3) . . ?
F1 C39 F2 102.2(3) . . ?
F3 C39 F2 104.7(3) . . ?
F1 C39 C33 114.1(3) . . ?
F3 C39 C33 113.5(3) . . ?
F2 C39 C33 112.8(3) . . ?
O2 C40 O1 123.4(2) . . ?
O2 C40 C36 122.0(2) . . ?
O1 C40 C36 114.61(19) . . ?

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
N4 S1 N3 C17 0.2(2) . . . . ?
N3 S1 N4 C18 0.0(2) . . . . ?
C15 N1 C1 C14 0.6(2) . . . . ?
C27 N1 C1 C14 169.8(2) . . . . ?
C15 N1 C1 C2 -178.9(2) . . . . ?
C27 N1 C1 C2 -9.7(4) . . . . ?
C14 C1 C2 C3 -178.4(2) . . . . ?
N1 C1 C2 C3 1.1(4) . . . . ?
C14 C1 C2 C7 1.0(3) . . . . ?
N1 C1 C2 C7 -179.6(2) . . . . ?
C7 C2 C3 C4 2.9(4) . . . . ?
C1 C2 C3 C4 -177.8(2) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
C4 C5 C6 C7 2.3(4) . . . . ?
C5 C6 C7 C2 -0.5(3) . . . . ?
C5 C6 C7 C8 179.1(2) . . . . ?
C3 C2 C7 C6 -2.1(3) . . . . ?
C1 C2 C7 C6 178.52(19) . . . . ?
C3 C2 C7 C8 178.3(2) . . . . ?
C1 C2 C7 C8 -1.1(3) . . . . ?
C6 C7 C8 C13 -178.4(2) . . . . ?
C2 C7 C8 C13 1.2(3) . . . . ?
C6 C7 C8 C9 1.9(3) . . . . ?
C2 C7 C8 C9 -178.5(2) . . . . ?
C13 C8 C9 C10 1.3(4) . . . . ?
C7 C8 C9 C10 -179.1(2) . . . . ?
C8 C9 C10 C11 -0.7(5) . . . . ?
C9 C10 C11 C12 -0.2(5) . . . . ?
C10 C11 C12 C13 0.4(5) . . . . ?
C11 C12 C13 C8 0.3(4) . . . . ?
C11 C12 C13 C14 -179.4(3) . . . . ?
C9 C8 C13 C12 -1.1(3) . . . . ?
C7 C8 C13 C12 179.2(2) . . . . ?
C9 C8 C13 C14 178.6(2) . . . . ?
C7 C8 C13 C14 -1.0(3) . . . . ?
N1 C1 C14 N2 -1.0(2) . . . . ?
C2 C1 C14 N2 178.55(19) . . . . ?
N1 C1 C14 C13 179.5(2) . . . . ?
C2 C1 C14 C13 -1.0(3) . . . . ?
C15 N2 C14 C1 1.1(2) . . . . ?
C15 N2 C14 C13 -179.5(2) . . . . ?
C12 C13 C14 C1 -179.3(2) . . . . ?
C8 C13 C14 C1 0.9(3) . . . . ?
C12 C13 C14 N2 1.2(4) . . . . ?
C8 C13 C14 N2 -178.5(2) . . . . ?
C14 N2 C15 N1 -0.7(2) . . . . ?
C14 N2 C15 C16 176.3(2) . . . . ?
C1 N1 C15 N2 0.1(2) . . . . ?
C27 N1 C15 N2 -169.5(2) . . . . ?
C1 N1 C15 C16 -176.8(2) . . . . ?
C27 N1 C15 C16 13.6(3) . . . . ?
N2 C15 C16 C21 69.7(3) . . . . ?
N1 C15 C16 C21 -113.6(3) . . . . ?
N2 C15 C16 C17 -102.2(3) . . . . ?
N1 C15 C16 C17 74.5(3) . . . . ?
S1 N3 C17 C16 176.8(2) . . . . ?
S1 N3 C17 C18 -0.3(3) . . . . ?
C21 C16 C17 N3 -177.8(2) . . . . ?
C15 C16 C17 N3 -5.5(4) . . . . ?
C21 C16 C17 C18 -0.9(3) . . . . ?
C15 C16 C17 C18 171.4(2) . . . . ?
S1 N4 C18 C19 179.6(2) . . . . ?
S1 N4 C18 C17 -0.1(3) . . . . ?
N3 C17 C18 N4 0.3(3) . . . . ?
C16 C17 C18 N4 -177.0(2) . . . . ?
N3 C17 C18 C19 -179.5(2) . . . . ?
C16 C17 C18 C19 3.3(3) . . . . ?
N4 C18 C19 C20 176.8(2) . . . . ?
C17 C18 C19 C20 -3.5(3) . . . . ?
N4 C18 C19 C22 -3.1(4) . . . . ?
C17 C18 C19 C22 176.6(2) . . . . ?
C18 C19 C20 C21 1.5(3) . . . . ?
C22 C19 C20 C21 -178.6(2) . . . . ?
C17 C16 C21 C20 -1.2(3) . . . . ?
C15 C16 C21 C20 -173.3(2) . . . . ?
C19 C20 C21 C16 0.9(4) . . . . ?
C20 C19 C22 C23 27.8(3) . . . . ?
C18 C19 C22 C23 -152.2(2) . . . . ?
C20 C19 C22 C26 -151.1(3) . . . . ?
C18 C19 C22 C26 28.8(4) . . . . ?
C26 C22 C23 C24 1.3(4) . . . . ?
C19 C22 C23 C24 -177.7(2) . . . . ?
C25 N5 C24 C23 0.4(4) . . . . ?
C22 C23 C24 N5 -1.6(4) . . . . ?
C24 N5 C25 C26 1.1(5) . . . . ?
N5 C25 C26 C22 -1.4(5) . . . . ?
C23 C22 C26 C25 0.1(4) . . . . ?
C19 C22 C26 C25 179.1(3) . . . . ?
C15 N1 C27 C28 78.3(3) . . . . ?
C1 N1 C27 C28 -89.0(3) . . . . ?
C15 N1 C27 C32 -103.4(3) . . . . ?
C1 N1 C27 C32 89.3(3) . . . . ?
C32 C27 C28 C29 -0.9(4) . . . . ?
N1 C27 C28 C29 177.4(2) . . . . ?
C27 C28 C29 C30 0.0(4) . . . . ?
C28 C29 C30 C31 0.6(5) . . . . ?
C29 C30 C31 C32 -0.4(4) . . . . ?
C28 C27 C32 C31 1.1(3) . . . . ?
N1 C27 C32 C31 -177.2(2) . . . . ?
C30 C31 C32 C27 -0.5(4) . . . . ?
C38 C33 C34 C35 -0.6(4) . . . . ?
C39 C33 C34 C35 176.8(3) . . . . ?
C33 C34 C35 C36 -0.3(4) . . . . ?
C34 C35 C36 C37 0.4(4) . . . . ?
C34 C35 C36 C40 -177.9(2) . . . . ?
C35 C36 C37 C38 0.5(4) . . . . ?
C40 C36 C37 C38 178.7(2) . . . . ?
C36 C37 C38 C33 -1.5(4) . . . . ?
C34 C33 C38 C37 1.5(4) . . . . ?
C39 C33 C38 C37 -175.9(3) . . . . ?
C38 C33 C39 F1 -78.0(4) . . . . ?
C34 C33 C39 F1 104.6(4) . . . . ?
C38 C33 C39 F3 157.0(3) . . . . ?
C34 C33 C39 F3 -20.4(5) . . . . ?
C38 C33 C39 F2 38.1(4) . . . . ?
C34 C33 C39 F2 -139.3(3) . . . . ?
C35 C36 C40 O2 -9.1(4) . . . . ?
C37 C36 C40 O2 172.7(3) . . . . ?
C35 C36 C40 O1 170.0(2) . . . . ?
C37 C36 C40 O1 -8.2(3) . . . . ?

#==============================================================================

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



#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/chloroform'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_mix_CN_BA
_database_code_depnum_ccdc_archive 'CCDC 1935322'
loop_
_audit_author_name
_audit_author_address
'Suguru Ito'
;YOKOHAMA National University
Japan
;
_audit_update_record             
;
2019-06-20 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C40 H24 N6 O2 S'
_chemical_formula_moiety         'C40 H24 N6 O2 S'
_chemical_formula_weight         652.73
_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                   9.72297(7)
_cell_length_b                   17.69375(11)
_cell_length_c                   18.28982(12)
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.3128(6)
_cell_angle_gamma                90.0000
_cell_volume                     3137.59(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19946
_cell_measurement_theta_min      4.86
_cell_measurement_theta_max      75.03
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_min          0.176
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1352.00
_exptl_absorpt_coefficient_mu    1.304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.696
_exptl_absorpt_correction_T_max  0.795

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

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            34401
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_theta_max         68.249
_diffrn_reflns_theta_min         4.850
_diffrn_reflns_theta_full        67.684
_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       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5741
_reflns_number_gt                5253
_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          0.0386
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0920
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         5741
_refine_ls_number_parameters     446
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0426P)²+1.1529P] 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         0.20
_refine_diff_density_min         -0.31
_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 0.0181 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 0.31277(4) 0.19423(2) 0.22414(2) 0.04765(12) Uani 1 1 d . . . . .
O1 O 0.09030(12) 0.54192(7) 0.17012(7) 0.0524(3) Uani 1 1 d . . . . .
H1 H 0.021(3) 0.5597(15) 0.1320(15) 0.102(8) Uiso 1 1 d . . . . .
O2 O -0.04582(15) 0.44214(9) 0.17864(9) 0.0864(5) Uani 1 1 d . . . . .
N1 N 0.79104(12) 0.26391(6) 0.29907(6) 0.0326(3) Uani 1 1 d . . . . .
N2 N 0.71780(12) 0.37440(7) 0.34236(6) 0.0356(3) Uani 1 1 d . . . . .
N3 N 0.45979(14) 0.22664(7) 0.25678(7) 0.0418(3) Uani 1 1 d . . . . .
N4 N 0.27647(13) 0.25066(7) 0.15660(7) 0.0417(3) Uani 1 1 d . . . . .
N5 N 0.09755(15) 0.41265(8) -0.07166(8) 0.0499(3) Uani 1 1 d . . . . .
N6 N 0.51169(17) 0.33394(10) 0.46552(9) 0.0647(4) Uani 1 1 d . . . . .
C1 C 0.86557(14) 0.27604(8) 0.36604(7) 0.0307(3) Uani 1 1 d . . . . .
C2 C 0.97886(14) 0.23560(8) 0.40285(7) 0.0324(3) Uani 1 1 d . . . . .
C3 C 1.04421(16) 0.17278(9) 0.37345(8) 0.0407(3) Uani 1 1 d . . . . .
H3 H 1.0075 0.1515 0.3291 0.049 Uiso 1 1 calc R U . . .
C4 C 1.16107(18) 0.14216(9) 0.40866(9) 0.0487(4) Uani 1 1 d . . . . .
H4 H 1.2052 0.1011 0.3876 0.058 Uiso 1 1 calc R U . . .
C5 C 1.21402(17) 0.17181(10) 0.47531(10) 0.0498(4) Uani 1 1 d . . . . .
H5 H 1.2937 0.1506 0.4994 0.060 Uiso 1 1 calc R U . . .
C6 C 1.15048(16) 0.23177(9) 0.50595(9) 0.0433(4) Uani 1 1 d . . . . .
H6 H 1.1866 0.2504 0.5516 0.052 Uiso 1 1 calc R U . . .
C7 C 1.03251(14) 0.26644(8) 0.47115(7) 0.0340(3) Uani 1 1 d . . . . .
C8 C 0.97259(14) 0.33410(8) 0.50188(7) 0.0348(3) Uani 1 1 d . . . . .
C9 C 1.01943(17) 0.36373(10) 0.57095(8) 0.0442(4) Uani 1 1 d . . . . .
H9 H 1.0894 0.3383 0.5995 0.053 Uiso 1 1 calc R U . . .
C10 C 0.96527(19) 0.42858(11) 0.59719(9) 0.0532(4) Uani 1 1 d . . . . .
H10 H 0.9985 0.4472 0.6433 0.064 Uiso 1 1 calc R U . . .
C11 C 0.86125(19) 0.46761(11) 0.55643(9) 0.0550(4) Uani 1 1 d . . . . .
H11 H 0.8253 0.5125 0.5748 0.066 Uiso 1 1 calc R U . . .
C12 C 0.81165(17) 0.44025(10) 0.48949(9) 0.0463(4) Uani 1 1 d . . . . .
H12 H 0.7406 0.4661 0.4623 0.056 Uiso 1 1 calc R U . . .
C13 C 0.86616(14) 0.37392(8) 0.46130(7) 0.0349(3) Uani 1 1 d . . . . .
C14 C 0.81674(14) 0.34337(8) 0.39163(7) 0.0324(3) Uani 1 1 d . . . . .
C15 C 0.70520(14) 0.32549(8) 0.28813(7) 0.0333(3) Uani 1 1 d . . . . .
C16 C 0.60531(14) 0.33374(8) 0.22380(7) 0.0343(3) Uani 1 1 d . . . . .
C17 C 0.48812(15) 0.28553(8) 0.21348(7) 0.0340(3) Uani 1 1 d . . . . .
C18 C 0.38331(14) 0.29923(8) 0.15568(7) 0.0342(3) Uani 1 1 d . . . . .
C19 C 0.39556(15) 0.36082(8) 0.10575(7) 0.0349(3) Uani 1 1 d . . . . .
C20 C 0.51128(16) 0.40499(9) 0.11767(8) 0.0406(3) Uani 1 1 d . . . . .
H20 H 0.5231 0.4457 0.0857 0.049 Uiso 1 1 calc R U . . .
C21 C 0.61369(15) 0.39231(9) 0.17565(8) 0.0397(3) Uani 1 1 d . . . . .
H21 H 0.6897 0.4252 0.1812 0.048 Uiso 1 1 calc R U . . .
C22 C 0.29042(15) 0.37729(8) 0.04485(8) 0.0367(3) Uani 1 1 d . . . . .
C23 C 0.27102(19) 0.45102(9) 0.01945(10) 0.0529(4) Uani 1 1 d . . . . .
H23 H 0.3237 0.4905 0.0416 0.063 Uiso 1 1 calc R U . . .
C24 C 0.1755(2) 0.46628(10) -0.03771(10) 0.0586(5) Uani 1 1 d . . . . .
H24 H 0.1643 0.5166 -0.0537 0.070 Uiso 1 1 calc R U . . .
C25 C 0.11627(17) 0.34154(9) -0.04837(9) 0.0462(4) Uani 1 1 d . . . . .
H25 H 0.0632 0.3032 -0.0723 0.055 Uiso 1 1 calc R U . . .
C26 C 0.20953(16) 0.32152(9) 0.00902(8) 0.0403(3) Uani 1 1 d . . . . .
H26 H 0.2184 0.2708 0.0238 0.048 Uiso 1 1 calc R U . . .
C27 C 0.81632(15) 0.20862(8) 0.24411(8) 0.0362(3) Uani 1 1 d . . . . .
C28 C 0.89567(17) 0.22990(10) 0.18760(8) 0.0460(4) Uani 1 1 d . . . . .
H28 H 0.9276 0.2799 0.1846 0.055 Uiso 1 1 calc R U . . .
C29 C 0.9273(2) 0.17727(12) 0.13601(10) 0.0594(5) Uani 1 1 d . . . . .
H29 H 0.9818 0.1911 0.0978 0.071 Uiso 1 1 calc R U . . .
C30 C 0.8796(2) 0.10508(12) 0.14029(10) 0.0631(5) Uani 1 1 d . . . . .
H30 H 0.9011 0.0696 0.1046 0.076 Uiso 1 1 calc R U . . .
C31 C 0.7996(2) 0.08299(10) 0.19659(11) 0.0591(5) Uani 1 1 d . . . . .
H31 H 0.7680 0.0329 0.1992 0.071 Uiso 1 1 calc R U . . .
C32 C 0.76690(17) 0.13587(9) 0.24911(9) 0.0459(4) Uani 1 1 d . . . . .
H32 H 0.7122 0.1222 0.2872 0.055 Uiso 1 1 calc R U . . .
C33 C 0.16669(15) 0.44443(8) 0.25068(8) 0.0372(3) Uani 1 1 d . . . . .
C34 C 0.13459(17) 0.38031(10) 0.28986(9) 0.0471(4) Uani 1 1 d . . . . .
H34 H 0.0482 0.3570 0.2804 0.057 Uiso 1 1 calc R U . . .
C35 C 0.22793(18) 0.35070(9) 0.34227(9) 0.0452(4) Uani 1 1 d . . . . .
H35 H 0.2058 0.3071 0.3683 0.054 Uiso 1 1 calc R U . . .
C36 C 0.35461(16) 0.38523(8) 0.35664(8) 0.0377(3) Uani 1 1 d . . . . .
C37 C 0.38946(15) 0.44790(9) 0.31624(8) 0.0409(3) Uani 1 1 d . . . . .
H37 H 0.4771 0.4700 0.3246 0.049 Uiso 1 1 calc R U . . .
C38 C 0.29576(15) 0.47751(8) 0.26406(8) 0.0398(3) Uani 1 1 d . . . . .
H38 H 0.3190 0.5204 0.2372 0.048 Uiso 1 1 calc R U . . .
C39 C 0.05953(16) 0.47598(10) 0.19611(9) 0.0464(4) Uani 1 1 d . . . . .
C40 C 0.44546(17) 0.35690(10) 0.41625(9) 0.0459(4) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# 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 N4 1.6067(13) . ?
S1 N3 1.6126(13) . ?
O1 C39 1.303(2) . ?
O1 H1 0.99(3) . ?
O2 C39 1.209(2) . ?
N1 C15 1.3780(18) . ?
N1 C1 1.3921(17) . ?
N1 C27 1.4369(17) . ?
N2 C15 1.3152(18) . ?
N2 C14 1.3814(17) . ?
N3 C17 1.3497(19) . ?
N4 C18 1.3493(19) . ?
N5 C25 1.336(2) . ?
N5 C24 1.338(2) . ?
N6 C40 1.142(2) . ?
C1 C14 1.3774(19) . ?
C1 C2 1.4377(19) . ?
C2 C3 1.407(2) . ?
C2 C7 1.4255(19) . ?
C3 C4 1.374(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.369(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.410(2) . ?
C6 H6 0.9400 . ?
C7 C8 1.462(2) . ?
C8 C9 1.411(2) . ?
C8 C13 1.415(2) . ?
C9 C10 1.365(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.394(3) . ?
C10 H10 0.9400 . ?
C11 C12 1.370(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.402(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.4334(18) . ?
C15 C16 1.4755(18) . ?
C16 C21 1.367(2) . ?
C16 C17 1.424(2) . ?
C17 C18 1.4327(19) . ?
C18 C19 1.432(2) . ?
C19 C20 1.374(2) . ?
C19 C22 1.4830(19) . ?
C20 C21 1.417(2) . ?
C20 H20 0.9400 . ?
C21 H21 0.9400 . ?
C22 C23 1.393(2) . ?
C22 C26 1.394(2) . ?
C23 C24 1.372(2) . ?
C23 H23 0.9400 . ?
C24 H24 0.9400 . ?
C25 C26 1.381(2) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?
C27 C32 1.380(2) . ?
C27 C28 1.387(2) . ?
C28 C29 1.377(2) . ?
C28 H28 0.9400 . ?
C29 C30 1.363(3) . ?
C29 H29 0.9400 . ?
C30 C31 1.392(3) . ?
C30 H30 0.9400 . ?
C31 C32 1.395(2) . ?
C31 H31 0.9400 . ?
C32 H32 0.9400 . ?
C33 C38 1.390(2) . ?
C33 C34 1.390(2) . ?
C33 C39 1.496(2) . ?
C34 C35 1.373(2) . ?
C34 H34 0.9400 . ?
C35 C36 1.382(2) . ?
C35 H35 0.9400 . ?
C36 C37 1.389(2) . ?
C36 C40 1.441(2) . ?
C37 C38 1.373(2) . ?
C37 H37 0.9400 . ?
C38 H38 0.9400 . ?

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
N4 S1 N3 101.59(7) . . ?
C39 O1 H1 112.3(15) . . ?
C15 N1 C1 105.98(11) . . ?
C15 N1 C27 124.77(11) . . ?
C1 N1 C27 127.98(11) . . ?
C15 N2 C14 104.55(11) . . ?
C17 N3 S1 105.77(10) . . ?
C18 N4 S1 106.30(10) . . ?
C25 N5 C24 117.45(14) . . ?
C14 C1 N1 105.21(11) . . ?
C14 C1 C2 122.88(12) . . ?
N1 C1 C2 131.69(12) . . ?
C3 C2 C7 119.42(13) . . ?
C3 C2 C1 124.49(13) . . ?
C7 C2 C1 115.91(12) . . ?
C4 C3 C2 120.89(14) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 120.06(15) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.19(15) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 121.96(15) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C6 C7 C2 117.45(13) . . ?
C6 C7 C8 121.12(13) . . ?
C2 C7 C8 121.34(12) . . ?
C9 C8 C13 117.29(14) . . ?
C9 C8 C7 122.49(13) . . ?
C13 C8 C7 120.19(12) . . ?
C10 C9 C8 121.34(15) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 120.82(14) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 119.69(16) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.47(15) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 120.38(13) . . ?
C12 C13 C14 122.13(13) . . ?
C8 C13 C14 117.49(13) . . ?
C1 C14 N2 111.29(11) . . ?
C1 C14 C13 121.81(12) . . ?
N2 C14 C13 126.90(13) . . ?
N2 C15 N1 112.94(12) . . ?
N2 C15 C16 123.70(12) . . ?
N1 C15 C16 123.31(12) . . ?
C21 C16 C17 117.04(12) . . ?
C21 C16 C15 121.42(13) . . ?
C17 C16 C15 121.23(13) . . ?
N3 C17 C16 125.52(13) . . ?
N3 C17 C18 113.47(13) . . ?
C16 C17 C18 120.93(13) . . ?
N4 C18 C19 126.41(13) . . ?
N4 C18 C17 112.87(13) . . ?
C19 C18 C17 120.69(13) . . ?
C20 C19 C18 115.98(12) . . ?
C20 C19 C22 121.16(13) . . ?
C18 C19 C22 122.86(13) . . ?
C19 C20 C21 123.35(14) . . ?
C19 C20 H20 118.3 . . ?
C21 C20 H20 118.3 . . ?
C16 C21 C20 121.99(14) . . ?
C16 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C23 C22 C26 116.65(13) . . ?
C23 C22 C19 120.20(13) . . ?
C26 C22 C19 123.13(13) . . ?
C24 C23 C22 120.36(15) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
N5 C24 C23 122.79(16) . . ?
N5 C24 H24 118.6 . . ?
C23 C24 H24 118.6 . . ?
N5 C25 C26 123.36(15) . . ?
N5 C25 H25 118.3 . . ?
C26 C25 H25 118.3 . . ?
C25 C26 C22 119.39(14) . . ?
C25 C26 H26 120.3 . . ?
C22 C26 H26 120.3 . . ?
C32 C27 C28 121.24(15) . . ?
C32 C27 N1 120.67(14) . . ?
C28 C27 N1 118.06(13) . . ?
C29 C28 C27 119.50(17) . . ?
C29 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C30 C29 C28 119.98(19) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C29 C30 C31 121.13(17) . . ?
C29 C30 H30 119.4 . . ?
C31 C30 H30 119.4 . . ?
C30 C31 C32 119.36(17) . . ?
C30 C31 H31 120.3 . . ?
C32 C31 H31 120.3 . . ?
C27 C32 C31 118.78(17) . . ?
C27 C32 H32 120.6 . . ?
C31 C32 H32 120.6 . . ?
C38 C33 C34 119.20(14) . . ?
C38 C33 C39 122.33(13) . . ?
C34 C33 C39 118.46(14) . . ?
C35 C34 C33 120.60(14) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C34 C35 C36 119.78(14) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
C35 C36 C37 120.10(14) . . ?
C35 C36 C40 118.48(14) . . ?
C37 C36 C40 121.35(14) . . ?
C38 C37 C36 119.92(14) . . ?
C38 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
C37 C38 C33 120.34(14) . . ?
C37 C38 H38 119.8 . . ?
C33 C38 H38 119.8 . . ?
O2 C39 O1 124.09(15) . . ?
O2 C39 C33 121.71(15) . . ?
O1 C39 C33 114.21(13) . . ?
N6 C40 C36 176.48(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
N4 S1 N3 C17 -0.51(11) . . . . ?
N3 S1 N4 C18 0.80(12) . . . . ?
C15 N1 C1 C14 1.45(15) . . . . ?
C27 N1 C1 C14 168.93(13) . . . . ?
C15 N1 C1 C2 -173.13(14) . . . . ?
C27 N1 C1 C2 -5.7(2) . . . . ?
C14 C1 C2 C3 -170.57(14) . . . . ?
N1 C1 C2 C3 3.2(2) . . . . ?
C14 C1 C2 C7 4.5(2) . . . . ?
N1 C1 C2 C7 178.23(13) . . . . ?
C7 C2 C3 C4 -1.8(2) . . . . ?
C1 C2 C3 C4 173.04(15) . . . . ?
C2 C3 C4 C5 1.9(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C7 -1.4(3) . . . . ?
C5 C6 C7 C2 1.4(2) . . . . ?
C5 C6 C7 C8 -175.10(15) . . . . ?
C3 C2 C7 C6 0.2(2) . . . . ?
C1 C2 C7 C6 -175.10(13) . . . . ?
C3 C2 C7 C8 176.67(13) . . . . ?
C1 C2 C7 C8 1.38(19) . . . . ?
C6 C7 C8 C9 -6.7(2) . . . . ?
C2 C7 C8 C9 176.94(14) . . . . ?
C6 C7 C8 C13 171.39(14) . . . . ?
C2 C7 C8 C13 -5.0(2) . . . . ?
C13 C8 C9 C10 -0.7(2) . . . . ?
C7 C8 C9 C10 177.50(15) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C11 C12 C13 -0.9(3) . . . . ?
C11 C12 C13 C8 0.4(3) . . . . ?
C11 C12 C13 C14 179.79(16) . . . . ?
C9 C8 C13 C12 0.4(2) . . . . ?
C7 C8 C13 C12 -177.82(14) . . . . ?
C9 C8 C13 C14 -179.04(13) . . . . ?
C7 C8 C13 C14 2.8(2) . . . . ?
N1 C1 C14 N2 -1.63(16) . . . . ?
C2 C1 C14 N2 173.55(12) . . . . ?
N1 C1 C14 C13 177.98(13) . . . . ?
C2 C1 C14 C13 -6.8(2) . . . . ?
C15 N2 C14 C1 1.13(16) . . . . ?
C15 N2 C14 C13 -178.46(14) . . . . ?
C12 C13 C14 C1 -176.44(14) . . . . ?
C8 C13 C14 C1 3.0(2) . . . . ?
C12 C13 C14 N2 3.1(2) . . . . ?
C8 C13 C14 N2 -177.48(13) . . . . ?
C14 N2 C15 N1 -0.15(16) . . . . ?
C14 N2 C15 C16 177.23(13) . . . . ?
C1 N1 C15 N2 -0.84(16) . . . . ?
C27 N1 C15 N2 -168.83(13) . . . . ?
C1 N1 C15 C16 -178.24(13) . . . . ?
C27 N1 C15 C16 13.8(2) . . . . ?
N2 C15 C16 C21 64.2(2) . . . . ?
N1 C15 C16 C21 -118.67(16) . . . . ?
N2 C15 C16 C17 -109.25(17) . . . . ?
N1 C15 C16 C17 67.87(19) . . . . ?
S1 N3 C17 C16 176.92(12) . . . . ?
S1 N3 C17 C18 0.07(15) . . . . ?
C21 C16 C17 N3 -177.62(14) . . . . ?
C15 C16 C17 N3 -3.9(2) . . . . ?
C21 C16 C17 C18 -1.0(2) . . . . ?
C15 C16 C17 C18 172.74(13) . . . . ?
S1 N4 C18 C19 -178.66(12) . . . . ?
S1 N4 C18 C17 -0.84(15) . . . . ?
N3 C17 C18 N4 0.53(18) . . . . ?
C16 C17 C18 N4 -176.49(13) . . . . ?
N3 C17 C18 C19 178.49(13) . . . . ?
C16 C17 C18 C19 1.5(2) . . . . ?
N4 C18 C19 C20 176.97(14) . . . . ?
C17 C18 C19 C20 -0.7(2) . . . . ?
N4 C18 C19 C22 -2.6(2) . . . . ?
C17 C18 C19 C22 179.74(13) . . . . ?
C18 C19 C20 C21 -0.5(2) . . . . ?
C22 C19 C20 C21 179.07(14) . . . . ?
C17 C16 C21 C20 -0.2(2) . . . . ?
C15 C16 C21 C20 -173.92(14) . . . . ?
C19 C20 C21 C16 1.0(2) . . . . ?
C20 C19 C22 C23 -28.3(2) . . . . ?
C18 C19 C22 C23 151.26(16) . . . . ?
C20 C19 C22 C26 150.00(16) . . . . ?
C18 C19 C22 C26 -30.5(2) . . . . ?
C26 C22 C23 C24 0.5(3) . . . . ?
C19 C22 C23 C24 178.89(17) . . . . ?
C25 N5 C24 C23 -0.6(3) . . . . ?
C22 C23 C24 N5 -0.1(3) . . . . ?
C24 N5 C25 C26 1.0(3) . . . . ?
N5 C25 C26 C22 -0.7(3) . . . . ?
C23 C22 C26 C25 -0.1(2) . . . . ?
C19 C22 C26 C25 -178.45(15) . . . . ?
C15 N1 C27 C32 -110.41(17) . . . . ?
C1 N1 C27 C32 84.29(19) . . . . ?
C15 N1 C27 C28 71.81(19) . . . . ?
C1 N1 C27 C28 -93.49(17) . . . . ?
C32 C27 C28 C29 -0.8(2) . . . . ?
N1 C27 C28 C29 176.91(14) . . . . ?
C27 C28 C29 C30 0.7(3) . . . . ?
C28 C29 C30 C31 -0.5(3) . . . . ?
C29 C30 C31 C32 0.6(3) . . . . ?
C28 C27 C32 C31 0.9(2) . . . . ?
N1 C27 C32 C31 -176.82(13) . . . . ?
C30 C31 C32 C27 -0.7(2) . . . . ?
C38 C33 C34 C35 1.3(2) . . . . ?
C39 C33 C34 C35 -177.85(16) . . . . ?
C33 C34 C35 C36 0.5(3) . . . . ?
C34 C35 C36 C37 -2.5(2) . . . . ?
C34 C35 C36 C40 174.60(16) . . . . ?
C35 C36 C37 C38 2.7(2) . . . . ?
C40 C36 C37 C38 -174.30(15) . . . . ?
C36 C37 C38 C33 -0.9(2) . . . . ?
C34 C33 C38 C37 -1.1(2) . . . . ?
C39 C33 C38 C37 178.04(15) . . . . ?
C38 C33 C39 O2 171.18(18) . . . . ?
C34 C33 C39 O2 -9.7(3) . . . . ?
C38 C33 C39 O1 -8.9(2) . . . . ?
C34 C33 C39 O1 170.20(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
O1 H1 N5 . . 3_565 2.5943(18) 0.986 1.608 177.7 no

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



#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/chloroform'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_nca2_with_BA
_database_code_depnum_ccdc_archive 'CCDC 1935320'
loop_
_audit_author_name
_audit_author_address
'Suguru Ito'
;YOKOHAMA National University
Japan
;
_audit_update_record             
;
2019-06-20 deposited with the CCDC.	2019-08-01 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C39 H25 N5 O2 S'
_chemical_formula_moiety         'C39 H25 N5 O2 S'
_chemical_formula_weight         627.72
_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                   9.93969(8)
_cell_length_b                   17.64482(16)
_cell_length_c                   17.57204(14)
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.1282(8)
_cell_angle_gamma                90.0000
_cell_volume                     3077.26(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22015
_cell_measurement_theta_min      3.54
_cell_measurement_theta_max      75.82
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.625
_exptl_crystal_size_mid          0.306
_exptl_crystal_size_min          0.204
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1304.00
_exptl_absorpt_coefficient_mu    1.296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.570
_exptl_absorpt_correction_T_max  0.768

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

_diffrn_ambient_temperature      223
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            33807
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_theta_max         68.247
_diffrn_reflns_theta_min         3.552
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5609
_reflns_number_gt                5220
_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          0.0374
_refine_ls_R_factor_gt           0.0355
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0927
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         5609
_refine_ls_number_parameters     428
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0468P)²+0.8121P] 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         0.18
_refine_diff_density_min         -0.35
_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 0.0181 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)
;
S S 0.3331 0.5567
;
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)
;

#==============================================================================
# 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 1.17090(4) 0.18548(2) 0.77474(2) 0.04115(11) Uani 1 1 d . . . . .
O1 O 0.41595(11) 0.54176(6) 0.82973(6) 0.0468(3) Uani 1 1 d . . . . .
H1 H 0.496(2) 0.5577(14) 0.8673(14) 0.093(7) Uiso 1 1 d . . . . .
O2 O 0.54629(13) 0.44101(8) 0.81592(9) 0.0786(5) Uani 1 1 d . . . . .
N1 N 0.69441(11) 0.26064(6) 0.70407(6) 0.0308(2) Uani 1 1 d . . . . .
N2 N 0.78300(11) 0.36587(6) 0.65566(6) 0.0346(3) Uani 1 1 d . . . . .
N3 N 1.02607(12) 0.21707(7) 0.74367(7) 0.0377(3) Uani 1 1 d . . . . .
N4 N 1.20834(11) 0.24342(7) 0.84324(6) 0.0362(3) Uani 1 1 d . . . . .
N5 N 1.39416(13) 0.40957(7) 1.07205(7) 0.0459(3) Uani 1 1 d . . . . .
C1 C 0.62291(12) 0.27472(7) 0.63523(7) 0.0288(3) Uani 1 1 d . . . . .
C2 C 0.50824(12) 0.23781(7) 0.59785(7) 0.0297(3) Uani 1 1 d . . . . .
C3 C 0.44242(14) 0.17423(8) 0.62669(8) 0.0360(3) Uani 1 1 d . . . . .
H3 H 0.4775 0.1510 0.6716 0.043 Uiso 1 1 calc R U . . .
C4 C 0.32737(15) 0.14562(8) 0.59004(8) 0.0415(3) Uani 1 1 d . . . . .
H4 H 0.2834 0.1038 0.6105 0.050 Uiso 1 1 calc R U . . .
C5 C 0.27644(15) 0.17868(9) 0.52276(8) 0.0422(3) Uani 1 1 d . . . . .
H5 H 0.1980 0.1591 0.4978 0.051 Uiso 1 1 calc R U . . .
C6 C 0.34007(14) 0.23977(8) 0.49260(8) 0.0383(3) Uani 1 1 d . . . . .
H6 H 0.3048 0.2609 0.4466 0.046 Uiso 1 1 calc R U . . .
C7 C 0.45687(13) 0.27189(7) 0.52859(7) 0.0305(3) Uani 1 1 d . . . . .
C8 C 0.52015(13) 0.33898(8) 0.49723(7) 0.0315(3) Uani 1 1 d . . . . .
C9 C 0.47175(15) 0.37348(9) 0.42866(8) 0.0395(3) Uani 1 1 d . . . . .
H9 H 0.3970 0.3523 0.4013 0.047 Uiso 1 1 calc R U . . .
C10 C 0.53121(16) 0.43706(9) 0.40112(8) 0.0463(4) Uani 1 1 d . . . . .
H10 H 0.4959 0.4593 0.3557 0.056 Uiso 1 1 calc R U . . .
C11 C 0.64343(17) 0.46931(9) 0.43962(9) 0.0474(4) Uani 1 1 d . . . . .
H11 H 0.6843 0.5126 0.4200 0.057 Uiso 1 1 calc R U . . .
C12 C 0.69384(15) 0.43724(8) 0.50646(8) 0.0407(3) Uani 1 1 d . . . . .
H12 H 0.7696 0.4587 0.5326 0.049 Uiso 1 1 calc R U . . .
C13 C 0.63301(13) 0.37272(7) 0.53602(7) 0.0315(3) Uani 1 1 d . . . . .
C14 C 0.68015(12) 0.33919(7) 0.60691(7) 0.0302(3) Uani 1 1 d . . . . .
C15 C 0.78782(13) 0.31792(7) 0.71301(7) 0.0320(3) Uani 1 1 d . . . . .
C16 C 0.88514(13) 0.32533(8) 0.77915(7) 0.0328(3) Uani 1 1 d . . . . .
C17 C 0.99956(13) 0.27674(7) 0.78845(7) 0.0313(3) Uani 1 1 d . . . . .
C18 C 1.10395(13) 0.29200(7) 0.84569(7) 0.0307(3) Uani 1 1 d . . . . .
C19 C 1.09413(13) 0.35504(7) 0.89631(7) 0.0312(3) Uani 1 1 d . . . . .
C20 C 0.98039(14) 0.39897(8) 0.88604(8) 0.0364(3) Uani 1 1 d . . . . .
H20 H 0.9698 0.4403 0.9189 0.044 Uiso 1 1 calc R U . . .
C21 C 0.87822(14) 0.38491(8) 0.82825(8) 0.0369(3) Uani 1 1 d . . . . .
H21 H 0.8035 0.4176 0.8237 0.044 Uiso 1 1 calc R U . . .
C22 C 1.19984(13) 0.37279(8) 0.95615(7) 0.0326(3) Uani 1 1 d . . . . .
C23 C 1.22382(16) 0.44746(8) 0.97887(9) 0.0457(4) Uani 1 1 d . . . . .
H23 H 1.1744 0.4872 0.9551 0.055 Uiso 1 1 calc R U . . .
C24 C 1.31982(18) 0.46306(9) 1.03598(10) 0.0519(4) Uani 1 1 d . . . . .
H24 H 1.3339 0.5139 1.0504 0.062 Uiso 1 1 calc R U . . .
C25 C 1.37215(15) 0.33785(9) 1.05059(8) 0.0415(3) Uani 1 1 d . . . . .
H25 H 1.4232 0.2995 1.0755 0.050 Uiso 1 1 calc R U . . .
C26 C 1.27810(14) 0.31724(8) 0.99354(8) 0.0359(3) Uani 1 1 d . . . . .
H26 H 1.2670 0.2660 0.9800 0.043 Uiso 1 1 calc R U . . .
C27 C 0.66499(13) 0.20608(8) 0.76194(7) 0.0332(3) Uani 1 1 d . . . . .
C28 C 0.71732(14) 0.13342(8) 0.75882(8) 0.0392(3) Uani 1 1 d . . . . .
H28 H 0.7745 0.1198 0.7202 0.047 Uiso 1 1 calc R U . . .
C29 C 0.68396(16) 0.08104(9) 0.81358(10) 0.0497(4) Uani 1 1 d . . . . .
H29 H 0.7181 0.0314 0.8120 0.060 Uiso 1 1 calc R U . . .
C30 C 0.60054(17) 0.10187(10) 0.87044(10) 0.0546(4) Uani 1 1 d . . . . .
H30 H 0.5782 0.0662 0.9074 0.066 Uiso 1 1 calc R U . . .
C31 C 0.54999(18) 0.17428(11) 0.87329(10) 0.0550(4) Uani 1 1 d . . . . .
H31 H 0.4933 0.1879 0.9122 0.066 Uiso 1 1 calc R U . . .
C32 C 0.58246(15) 0.22732(9) 0.81895(8) 0.0431(3) Uani 1 1 d . . . . .
H32 H 0.5488 0.2770 0.8209 0.052 Uiso 1 1 calc R U . . .
C33 C 0.33009(13) 0.44333(8) 0.75139(7) 0.0330(3) Uani 1 1 d . . . . .
C34 C 0.35215(14) 0.37764(8) 0.71018(8) 0.0383(3) Uani 1 1 d . . . . .
H34 H 0.4369 0.3539 0.7144 0.046 Uiso 1 1 calc R U . . .
C35 C 0.25057(15) 0.34705(8) 0.66310(8) 0.0412(3) Uani 1 1 d . . . . .
H35 H 0.2662 0.3026 0.6355 0.049 Uiso 1 1 calc R U . . .
C36 C 0.12574(14) 0.38180(8) 0.65657(8) 0.0408(3) Uani 1 1 d . . . . .
H36 H 0.0566 0.3612 0.6243 0.049 Uiso 1 1 calc R U . . .
C37 C 0.10288(14) 0.44682(8) 0.69752(9) 0.0413(3) Uani 1 1 d . . . . .
H37 H 0.0176 0.4699 0.6935 0.050 Uiso 1 1 calc R U . . .
C38 C 0.20390(14) 0.47818(8) 0.74418(8) 0.0361(3) Uani 1 1 d . . . . .
H38 H 0.1879 0.5230 0.7711 0.043 Uiso 1 1 calc R U . . .
C39 C 0.44176(14) 0.47471(8) 0.80186(8) 0.0402(3) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'

#==============================================================================
# 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 N4 1.6074(12) . ?
S1 N3 1.6110(12) . ?
O1 C39 1.3112(17) . ?
O1 H1 1.04(2) . ?
O2 C39 1.2108(18) . ?
N1 C15 1.3755(16) . ?
N1 C1 1.3915(16) . ?
N1 C27 1.4419(16) . ?
N2 C15 1.3147(17) . ?
N2 C14 1.3803(16) . ?
N3 C17 1.3490(18) . ?
N4 C18 1.3484(17) . ?
N5 C25 1.3351(19) . ?
N5 C24 1.337(2) . ?
C1 C14 1.3772(18) . ?
C1 C2 1.4398(17) . ?
C2 C3 1.4069(18) . ?
C2 C7 1.4268(18) . ?
C3 C4 1.3774(19) . ?
C3 H3 0.9400 . ?
C4 C5 1.389(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.371(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.4103(18) . ?
C6 H6 0.9400 . ?
C7 C8 1.4623(19) . ?
C8 C9 1.4109(18) . ?
C8 C13 1.4121(18) . ?
C9 C10 1.369(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.394(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.373(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.4021(19) . ?
C12 H12 0.9400 . ?
C13 C14 1.4344(17) . ?
C15 C16 1.4768(18) . ?
C16 C21 1.364(2) . ?
C16 C17 1.4265(19) . ?
C17 C18 1.4307(17) . ?
C18 C19 1.4309(18) . ?
C19 C20 1.3745(19) . ?
C19 C22 1.4790(17) . ?
C20 C21 1.4181(18) . ?
C20 H20 0.9400 . ?
C21 H21 0.9400 . ?
C22 C26 1.3935(19) . ?
C22 C23 1.393(2) . ?
C23 C24 1.374(2) . ?
C23 H23 0.9400 . ?
C24 H24 0.9400 . ?
C25 C26 1.3815(19) . ?
C25 H25 0.9400 . ?
C26 H26 0.9400 . ?
C27 C32 1.381(2) . ?
C27 C28 1.386(2) . ?
C28 C29 1.387(2) . ?
C28 H28 0.9400 . ?
C29 C30 1.383(3) . ?
C29 H29 0.9400 . ?
C30 C31 1.375(3) . ?
C30 H30 0.9400 . ?
C31 C32 1.388(2) . ?
C31 H31 0.9400 . ?
C32 H32 0.9400 . ?
C33 C34 1.3904(19) . ?
C33 C38 1.3964(19) . ?
C33 C39 1.4892(19) . ?
C34 C35 1.380(2) . ?
C34 H34 0.9400 . ?
C35 C36 1.383(2) . ?
C35 H35 0.9400 . ?
C36 C37 1.380(2) . ?
C36 H36 0.9400 . ?
C37 C38 1.377(2) . ?
C37 H37 0.9400 . ?
C38 H38 0.9400 . ?

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
N4 S1 N3 101.52(6) . . ?
C39 O1 H1 108.9(13) . . ?
C15 N1 C1 106.12(10) . . ?
C15 N1 C27 124.87(10) . . ?
C1 N1 C27 128.22(10) . . ?
C15 N2 C14 104.54(11) . . ?
C17 N3 S1 105.77(9) . . ?
C18 N4 S1 106.33(9) . . ?
C25 N5 C24 117.23(12) . . ?
C14 C1 N1 105.08(11) . . ?
C14 C1 C2 122.76(11) . . ?
N1 C1 C2 132.07(12) . . ?
C3 C2 C7 119.44(12) . . ?
C3 C2 C1 124.63(12) . . ?
C7 C2 C1 115.86(11) . . ?
C4 C3 C2 120.95(13) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.93(13) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.32(13) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 121.90(13) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C6 C7 C2 117.43(12) . . ?
C6 C7 C8 121.12(12) . . ?
C2 C7 C8 121.42(11) . . ?
C9 C8 C13 117.07(13) . . ?
C9 C8 C7 122.51(12) . . ?
C13 C8 C7 120.41(11) . . ?
C10 C9 C8 121.46(14) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 120.84(13) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 119.45(14) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 120.45(14) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 120.72(12) . . ?
C12 C13 C14 121.98(12) . . ?
C8 C13 C14 117.29(12) . . ?
C1 C14 N2 111.35(11) . . ?
C1 C14 C13 122.19(11) . . ?
N2 C14 C13 126.45(12) . . ?
N2 C15 N1 112.91(11) . . ?
N2 C15 C16 122.75(12) . . ?
N1 C15 C16 124.33(11) . . ?
C21 C16 C17 117.27(12) . . ?
C21 C16 C15 120.84(12) . . ?
C17 C16 C15 121.39(12) . . ?
N3 C17 C16 125.61(12) . . ?
N3 C17 C18 113.56(12) . . ?
C16 C17 C18 120.70(12) . . ?
N4 C18 C17 112.81(12) . . ?
N4 C18 C19 126.35(12) . . ?
C17 C18 C19 120.79(12) . . ?
C20 C19 C18 116.12(11) . . ?
C20 C19 C22 121.42(12) . . ?
C18 C19 C22 122.46(12) . . ?
C19 C20 C21 123.17(13) . . ?
C19 C20 H20 118.4 . . ?
C21 C20 H20 118.4 . . ?
C16 C21 C20 121.92(13) . . ?
C16 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C26 C22 C23 116.60(12) . . ?
C26 C22 C19 122.88(12) . . ?
C23 C22 C19 120.51(12) . . ?
C24 C23 C22 119.97(14) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
N5 C24 C23 123.26(14) . . ?
N5 C24 H24 118.4 . . ?
C23 C24 H24 118.4 . . ?
N5 C25 C26 123.26(13) . . ?
N5 C25 H25 118.4 . . ?
C26 C25 H25 118.4 . . ?
C25 C26 C22 119.68(13) . . ?
C25 C26 H26 120.2 . . ?
C22 C26 H26 120.2 . . ?
C32 C27 C28 121.27(13) . . ?
C32 C27 N1 118.80(12) . . ?
C28 C27 N1 119.92(13) . . ?
C27 C28 C29 118.98(15) . . ?
C27 C28 H28 120.5 . . ?
C29 C28 H28 120.5 . . ?
C30 C29 C28 119.97(15) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C31 C30 C29 120.55(15) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C30 C31 C32 120.17(16) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C27 C32 C31 119.06(15) . . ?
C27 C32 H32 120.5 . . ?
C31 C32 H32 120.5 . . ?
C34 C33 C38 119.09(13) . . ?
C34 C33 C39 119.11(12) . . ?
C38 C33 C39 121.81(12) . . ?
C35 C34 C33 120.48(13) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C34 C35 C36 120.00(13) . . ?
C34 C35 H35 120.0 . . ?
C36 C35 H35 120.0 . . ?
C37 C36 C35 119.86(13) . . ?
C37 C36 H36 120.1 . . ?
C35 C36 H36 120.1 . . ?
C38 C37 C36 120.60(13) . . ?
C38 C37 H37 119.7 . . ?
C36 C37 H37 119.7 . . ?
C37 C38 C33 119.96(13) . . ?
C37 C38 H38 120.0 . . ?
C33 C38 H38 120.0 . . ?
O2 C39 O1 123.38(14) . . ?
O2 C39 C33 122.84(14) . . ?
O1 C39 C33 113.77(12) . . ?

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
N4 S1 N3 C17 -0.60(10) . . . . ?
N3 S1 N4 C18 0.63(10) . . . . ?
C15 N1 C1 C14 0.92(14) . . . . ?
C27 N1 C1 C14 170.98(12) . . . . ?
C15 N1 C1 C2 -175.46(13) . . . . ?
C27 N1 C1 C2 -5.4(2) . . . . ?
C14 C1 C2 C3 -176.60(13) . . . . ?
N1 C1 C2 C3 -0.8(2) . . . . ?
C14 C1 C2 C7 0.38(18) . . . . ?
N1 C1 C2 C7 176.23(12) . . . . ?
C7 C2 C3 C4 -1.6(2) . . . . ?
C1 C2 C3 C4 175.28(13) . . . . ?
C2 C3 C4 C5 1.3(2) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C4 C5 C6 C7 -1.0(2) . . . . ?
C5 C6 C7 C2 0.7(2) . . . . ?
C5 C6 C7 C8 -177.44(13) . . . . ?
C3 C2 C7 C6 0.59(18) . . . . ?
C1 C2 C7 C6 -176.56(11) . . . . ?
C3 C2 C7 C8 178.70(12) . . . . ?
C1 C2 C7 C8 1.55(18) . . . . ?
C6 C7 C8 C9 -2.3(2) . . . . ?
C2 C7 C8 C9 179.65(12) . . . . ?
C6 C7 C8 C13 176.77(12) . . . . ?
C2 C7 C8 C13 -1.27(19) . . . . ?
C13 C8 C9 C10 -0.3(2) . . . . ?
C7 C8 C9 C10 178.82(13) . . . . ?
C8 C9 C10 C11 1.0(2) . . . . ?
C9 C10 C11 C12 -0.7(2) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C11 C12 C13 C8 0.8(2) . . . . ?
C11 C12 C13 C14 -177.90(14) . . . . ?
C9 C8 C13 C12 -0.60(19) . . . . ?
C7 C8 C13 C12 -179.73(12) . . . . ?
C9 C8 C13 C14 178.20(12) . . . . ?
C7 C8 C13 C14 -0.93(18) . . . . ?
N1 C1 C14 N2 -0.57(14) . . . . ?
C2 C1 C14 N2 176.23(11) . . . . ?
N1 C1 C14 C13 -179.49(11) . . . . ?
C2 C1 C14 C13 -2.7(2) . . . . ?
C15 N2 C14 C1 -0.03(15) . . . . ?
C15 N2 C14 C13 178.83(13) . . . . ?
C12 C13 C14 C1 -178.33(13) . . . . ?
C8 C13 C14 C1 2.90(19) . . . . ?
C12 C13 C14 N2 2.9(2) . . . . ?
C8 C13 C14 N2 -175.85(12) . . . . ?
C14 N2 C15 N1 0.66(15) . . . . ?
C14 N2 C15 C16 -179.98(12) . . . . ?
C1 N1 C15 N2 -1.03(15) . . . . ?
C27 N1 C15 N2 -171.51(12) . . . . ?
C1 N1 C15 C16 179.62(12) . . . . ?
C27 N1 C15 C16 9.1(2) . . . . ?
N2 C15 C16 C21 66.37(19) . . . . ?
N1 C15 C16 C21 -114.34(15) . . . . ?
N2 C15 C16 C17 -105.21(16) . . . . ?
N1 C15 C16 C17 74.08(18) . . . . ?
S1 N3 C17 C16 176.09(11) . . . . ?
S1 N3 C17 C18 0.39(14) . . . . ?
C21 C16 C17 N3 -177.30(13) . . . . ?
C15 C16 C17 N3 -5.4(2) . . . . ?
C21 C16 C17 C18 -1.88(19) . . . . ?
C15 C16 C17 C18 169.98(12) . . . . ?
S1 N4 C18 C17 -0.46(13) . . . . ?
S1 N4 C18 C19 -178.02(11) . . . . ?
N3 C17 C18 N4 0.05(16) . . . . ?
C16 C17 C18 N4 -175.89(12) . . . . ?
N3 C17 C18 C19 177.76(12) . . . . ?
C16 C17 C18 C19 1.82(19) . . . . ?
N4 C18 C19 C20 177.10(13) . . . . ?
C17 C18 C19 C20 -0.28(18) . . . . ?
N4 C18 C19 C22 -2.6(2) . . . . ?
C17 C18 C19 C22 -179.93(12) . . . . ?
C18 C19 C20 C21 -1.1(2) . . . . ?
C22 C19 C20 C21 178.51(13) . . . . ?
C17 C16 C21 C20 0.5(2) . . . . ?
C15 C16 C21 C20 -171.42(13) . . . . ?
C19 C20 C21 C16 1.1(2) . . . . ?
C20 C19 C22 C26 148.28(14) . . . . ?
C18 C19 C22 C26 -32.09(19) . . . . ?
C20 C19 C22 C23 -30.5(2) . . . . ?
C18 C19 C22 C23 149.16(14) . . . . ?
C26 C22 C23 C24 -0.6(2) . . . . ?
C19 C22 C23 C24 178.23(15) . . . . ?
C25 N5 C24 C23 -0.1(3) . . . . ?
C22 C23 C24 N5 0.2(3) . . . . ?
C24 N5 C25 C26 0.3(2) . . . . ?
N5 C25 C26 C22 -0.8(2) . . . . ?
C23 C22 C26 C25 0.8(2) . . . . ?
C19 C22 C26 C25 -177.95(13) . . . . ?
C15 N1 C27 C32 79.28(17) . . . . ?
C1 N1 C27 C32 -89.06(17) . . . . ?
C15 N1 C27 C28 -101.90(16) . . . . ?
C1 N1 C27 C28 89.76(17) . . . . ?
C32 C27 C28 C29 1.0(2) . . . . ?
N1 C27 C28 C29 -177.79(12) . . . . ?
C27 C28 C29 C30 -0.5(2) . . . . ?
C28 C29 C30 C31 0.0(2) . . . . ?
C29 C30 C31 C32 0.0(3) . . . . ?
C28 C27 C32 C31 -1.0(2) . . . . ?
N1 C27 C32 C31 177.78(13) . . . . ?
C30 C31 C32 C27 0.5(3) . . . . ?
C38 C33 C34 C35 -0.3(2) . . . . ?
C39 C33 C34 C35 179.81(13) . . . . ?
C33 C34 C35 C36 0.1(2) . . . . ?
C34 C35 C36 C37 -0.3(2) . . . . ?
C35 C36 C37 C38 0.9(2) . . . . ?
C36 C37 C38 C33 -1.2(2) . . . . ?
C34 C33 C38 C37 0.9(2) . . . . ?
C39 C33 C38 C37 -179.27(13) . . . . ?
C34 C33 C39 O2 -9.0(2) . . . . ?
C38 C33 C39 O2 171.11(16) . . . . ?
C34 C33 C39 O1 171.25(13) . . . . ?
C38 C33 C39 O1 -8.6(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
O1 H1 N5 . . 3_767 2.6312(16) 1.041 1.595 173.0 no

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



#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/chloroform'
_exptl_crystal_preparation       Luminescent
