# Electronic Supplementary Material (ESI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2020

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

data_sta150Ph_PhMe
_database_code_depnum_ccdc_archive 'CCDC 1995249'
loop_
_audit_author_name
_audit_author_address
'Suguru Ito'
;Yokohama National University
Japan
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-01 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C34 H22 N4 S'
_chemical_formula_moiety         'C34 H22 N4 S'
_chemical_formula_weight         518.63
_chemical_melting_point          498.75-500.55

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
#------------------------------------------------------------------------------
_cell_length_a                   13.13381(11)
_cell_length_b                   16.14963(13)
_cell_length_c                   24.1369(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.3385(7)
_cell_angle_gamma                90.0000
_cell_volume                     5104.92(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10255
_cell_measurement_theta_min      3.68
_cell_measurement_theta_max      74.08
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.481
_exptl_crystal_size_mid          0.398
_exptl_crystal_size_min          0.360
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2160.00
_exptl_absorpt_coefficient_mu    1.368
_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  0.280
_exptl_absorpt_correction_T_max  0.611

#==============================================================================
# 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            15141
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_theta_max         68.231
_diffrn_reflns_theta_min         3.673
_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       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4685
_reflns_number_gt                4315
_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          0.0478
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1217
_refine_ls_wR_factor_gt          0.1188
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4685
_refine_ls_number_parameters     352
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0705P)²+2.8786P] 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         -0.48
_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 0.25791(3) 0.42547(3) 0.42880(3) 0.06120(18) Uani 1 1 d . . . . .
N1 N 0.02295(9) 0.15982(7) 0.34724(5) 0.0338(3) Uani 1 1 d . . . . .
N2 N 0.13774(10) 0.22369(8) 0.29746(5) 0.0377(3) Uani 1 1 d . . . . .
N3 N 0.20853(10) 0.34761(9) 0.39486(7) 0.0494(4) Uani 1 1 d . . . . .
N4 N 0.16032(10) 0.48426(8) 0.43275(6) 0.0453(3) Uani 1 1 d . . . . .
C1 C 0.07468(11) 0.09795(9) 0.32050(6) 0.0337(3) Uani 1 1 d . . . . .
C2 C 0.06445(12) 0.00938(9) 0.32112(6) 0.0363(3) Uani 1 1 d . . . . .
C3 C -0.01236(14) -0.03382(10) 0.34656(7) 0.0441(4) Uani 1 1 d . . . . .
H3 H -0.0621 -0.0041 0.3644 0.053 Uiso 1 1 calc R U . . .
C4 C -0.01577(16) -0.11876(11) 0.34572(8) 0.0541(5) Uani 1 1 d . . . . .
H4 H -0.0675 -0.1469 0.3630 0.065 Uiso 1 1 calc R U . . .
C5 C 0.05741(17) -0.16319(11) 0.31930(9) 0.0609(5) Uani 1 1 d . . . . .
H5 H 0.0559 -0.2214 0.3194 0.073 Uiso 1 1 calc R U . . .
C6 C 0.13170(15) -0.12233(11) 0.29312(8) 0.0518(4) Uani 1 1 d . . . . .
H6 H 0.1799 -0.1534 0.2751 0.062 Uiso 1 1 calc R U . . .
C7 C 0.13807(12) -0.03539(10) 0.29245(6) 0.0390(4) Uani 1 1 d . . . . .
C8 C 0.21694(12) 0.00756(10) 0.26372(6) 0.0377(3) Uani 1 1 d . . . . .
C9 C 0.29678(14) -0.03481(11) 0.23960(6) 0.0453(4) Uani 1 1 d . . . . .
H9 H 0.2967 -0.0930 0.2391 0.054 Uiso 1 1 calc R U . . .
C10 C 0.37411(14) 0.00706(12) 0.21692(7) 0.0503(4) Uani 1 1 d . . . . .
H10 H 0.4274 -0.0228 0.2024 0.060 Uiso 1 1 calc R U . . .
C11 C 0.37506(15) 0.09308(12) 0.21501(7) 0.0507(4) Uani 1 1 d . . . . .
H11 H 0.4280 0.1211 0.1987 0.061 Uiso 1 1 calc R U . . .
C12 C 0.29782(13) 0.13680(11) 0.23715(6) 0.0444(4) Uani 1 1 d . . . . .
H12 H 0.2977 0.1950 0.2357 0.053 Uiso 1 1 calc R U . . .
C13 C 0.21927(12) 0.09510(10) 0.26188(6) 0.0367(3) Uani 1 1 d . . . . .
C14 C 0.14400(12) 0.13902(9) 0.29067(6) 0.0350(3) Uani 1 1 d . . . . .
C15 C 0.06575(11) 0.23377(9) 0.33197(6) 0.0351(3) Uani 1 1 d . . . . .
C16 C 0.03533(11) 0.31410(9) 0.35458(6) 0.0337(3) Uani 1 1 d . . . . .
C17 C 0.10902(11) 0.36534(9) 0.38456(6) 0.0344(3) Uani 1 1 d . . . . .
C18 C 0.08069(11) 0.44398(9) 0.40664(6) 0.0333(3) Uani 1 1 d . . . . .
C19 C -0.02216(11) 0.47369(8) 0.39922(6) 0.0313(3) Uani 1 1 d . . . . .
C20 C -0.09033(12) 0.42122(9) 0.37080(6) 0.0352(3) Uani 1 1 d . . . . .
H20 H -0.1591 0.4375 0.3659 0.042 Uiso 1 1 calc R U . . .
C21 C -0.06223(12) 0.34395(9) 0.34860(6) 0.0372(3) Uani 1 1 d . . . . .
H21 H -0.1128 0.3120 0.3290 0.045 Uiso 1 1 calc R U . . .
C22 C -0.05370(12) 0.55576(9) 0.41927(6) 0.0345(3) Uani 1 1 d . . . . .
C23 C -0.00189(12) 0.59584(9) 0.46426(6) 0.0385(3) Uani 1 1 d . . . . .
H23 H 0.0560 0.5707 0.4824 0.046 Uiso 1 1 calc R U . . .
C24 C -0.03431(14) 0.67187(10) 0.48251(7) 0.0459(4) Uani 1 1 d . . . . .
H24 H 0.0018 0.6980 0.5127 0.055 Uiso 1 1 calc R U . . .
C25 C -0.11918(16) 0.70945(11) 0.45662(9) 0.0613(5) Uani 1 1 d . . . . .
H25 H -0.1423 0.7604 0.4697 0.074 Uiso 1 1 calc R U . . .
C26 C -0.17002(19) 0.67157(13) 0.41128(11) 0.0781(8) Uani 1 1 d . . . . .
H26 H -0.2269 0.6976 0.3928 0.094 Uiso 1 1 calc R U . . .
C27 C -0.13764(16) 0.59568(12) 0.39299(9) 0.0604(5) Uani 1 1 d . . . . .
H27 H -0.1731 0.5706 0.3621 0.072 Uiso 1 1 calc R U . . .
C28 C -0.03596(11) 0.14809(8) 0.39476(6) 0.0328(3) Uani 1 1 d . . . . .
C29 C -0.13980(12) 0.16124(10) 0.39082(7) 0.0406(3) Uani 1 1 d . . . . .
H29 H -0.1735 0.1779 0.3569 0.049 Uiso 1 1 calc R U . . .
C30 C -0.19456(13) 0.14974(11) 0.43730(7) 0.0468(4) Uani 1 1 d . . . . .
H30 H -0.2654 0.1593 0.4346 0.056 Uiso 1 1 calc R U . . .
C31 C -0.14664(13) 0.12450(10) 0.48754(7) 0.0440(4) Uani 1 1 d . . . . .
C32 C -0.04224(13) 0.11034(11) 0.49030(7) 0.0456(4) Uani 1 1 d . . . . .
H32 H -0.0086 0.0922 0.5239 0.055 Uiso 1 1 calc R U . . .
C33 C 0.01349(12) 0.12244(10) 0.44441(6) 0.0399(3) Uani 1 1 d . . . . .
H33 H 0.0844 0.1133 0.4470 0.048 Uiso 1 1 calc R U . . .
C34 C -0.20712(17) 0.11131(16) 0.53771(9) 0.0662(6) Uani 1 1 d . . . . .
H34A H -0.1615 0.0938 0.5690 0.079 Uiso 1 1 calc R U . . .
H34B H -0.2403 0.1627 0.5468 0.079 Uiso 1 1 calc R U . . .
H34C H -0.2584 0.0690 0.5295 0.079 Uiso 1 1 calc R U . . .


#==============================================================================
_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 1.6038(13) . ?
S1 N3 1.6102(15) . ?
N1 C15 1.3819(19) . ?
N1 C1 1.3939(18) . ?
N1 C28 1.4436(18) . ?
N2 C15 1.3166(19) . ?
N2 C14 1.3803(19) . ?
N3 C17 1.343(2) . ?
N4 C18 1.347(2) . ?
C1 C14 1.374(2) . ?
C1 C2 1.437(2) . ?
C2 C3 1.406(2) . ?
C2 C7 1.427(2) . ?
C3 C4 1.372(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.392(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.371(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.407(2) . ?
C6 H6 0.9400 . ?
C7 C8 1.464(2) . ?
C8 C9 1.414(2) . ?
C8 C13 1.415(2) . ?
C9 C10 1.368(3) . ?
C9 H9 0.9400 . ?
C10 C11 1.390(3) . ?
C10 H10 0.9400 . ?
C11 C12 1.377(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.403(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.4379(19) . ?
C15 C16 1.4743(19) . ?
C16 C21 1.367(2) . ?
C16 C17 1.428(2) . ?
C17 C18 1.437(2) . ?
C18 C19 1.432(2) . ?
C19 C20 1.377(2) . ?
C19 C22 1.4808(19) . ?
C20 C21 1.418(2) . ?
C20 H20 0.9400 . ?
C21 H21 0.9400 . ?
C22 C27 1.388(2) . ?
C22 C23 1.396(2) . ?
C23 C24 1.383(2) . ?
C23 H23 0.9400 . ?
C24 C25 1.377(3) . ?
C24 H24 0.9400 . ?
C25 C26 1.381(3) . ?
C25 H25 0.9400 . ?
C26 C27 1.381(3) . ?
C26 H26 0.9400 . ?
C27 H27 0.9400 . ?
C28 C29 1.376(2) . ?
C28 C33 1.383(2) . ?
C29 C30 1.390(2) . ?
C29 H29 0.9400 . ?
C30 C31 1.385(3) . ?
C30 H30 0.9400 . ?
C31 C32 1.387(2) . ?
C31 C34 1.513(2) . ?
C32 C33 1.387(2) . ?
C32 H32 0.9400 . ?
C33 H33 0.9400 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 H34C 0.9700 . ?

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 101.51(7) . . ?
C15 N1 C1 105.88(12) . . ?
C15 N1 C28 125.35(12) . . ?
C1 N1 C28 125.67(12) . . ?
C15 N2 C14 104.46(12) . . ?
C17 N3 S1 106.06(11) . . ?
C18 N4 S1 106.38(10) . . ?
C14 C1 N1 105.20(13) . . ?
C14 C1 C2 123.53(13) . . ?
N1 C1 C2 131.27(14) . . ?
C3 C2 C7 119.69(14) . . ?
C3 C2 C1 124.71(14) . . ?
C7 C2 C1 115.59(14) . . ?
C4 C3 C2 120.89(16) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.93(17) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.21(16) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 122.05(16) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C6 C7 C2 117.19(15) . . ?
C6 C7 C8 121.54(14) . . ?
C2 C7 C8 121.27(14) . . ?
C9 C8 C13 116.88(15) . . ?
C9 C8 C7 122.62(15) . . ?
C13 C8 C7 120.40(13) . . ?
C10 C9 C8 121.44(16) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 121.06(15) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 119.40(17) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 120.41(16) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 120.77(14) . . ?
C12 C13 C14 121.57(14) . . ?
C8 C13 C14 117.42(14) . . ?
C1 C14 N2 111.61(12) . . ?
C1 C14 C13 121.49(14) . . ?
N2 C14 C13 126.54(14) . . ?
N2 C15 N1 112.83(12) . . ?
N2 C15 C16 124.80(14) . . ?
N1 C15 C16 122.32(12) . . ?
C21 C16 C17 116.31(13) . . ?
C21 C16 C15 123.34(14) . . ?
C17 C16 C15 120.36(13) . . ?
N3 C17 C16 125.67(13) . . ?
N3 C17 C18 113.30(14) . . ?
C16 C17 C18 121.03(13) . . ?
N4 C18 C19 126.03(13) . . ?
N4 C18 C17 112.75(13) . . ?
C19 C18 C17 121.20(14) . . ?
C20 C19 C18 115.31(13) . . ?
C20 C19 C22 121.74(13) . . ?
C18 C19 C22 122.93(13) . . ?
C19 C20 C21 123.48(14) . . ?
C19 C20 H20 118.3 . . ?
C21 C20 H20 118.3 . . ?
C16 C21 C20 122.64(14) . . ?
C16 C21 H21 118.7 . . ?
C20 C21 H21 118.7 . . ?
C27 C22 C23 117.61(14) . . ?
C27 C22 C19 119.89(14) . . ?
C23 C22 C19 122.49(13) . . ?
C24 C23 C22 121.05(15) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C25 C24 C23 120.34(16) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 119.38(16) . . ?
C24 C25 H25 120.3 . . ?
C26 C25 H25 120.3 . . ?
C27 C26 C25 120.30(18) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C22 121.28(17) . . ?
C26 C27 H27 119.4 . . ?
C22 C27 H27 119.4 . . ?
C29 C28 C33 120.26(14) . . ?
C29 C28 N1 120.85(13) . . ?
C33 C28 N1 118.89(13) . . ?
C28 C29 C30 119.61(15) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
C31 C30 C29 121.17(15) . . ?
C31 C30 H30 119.4 . . ?
C29 C30 H30 119.4 . . ?
C30 C31 C32 118.22(14) . . ?
C30 C31 C34 120.74(17) . . ?
C32 C31 C34 121.03(17) . . ?
C31 C32 C33 121.20(16) . . ?
C31 C32 H32 119.4 . . ?
C33 C32 H32 119.4 . . ?
C28 C33 C32 119.53(15) . . ?
C28 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 S1 N3 C17 0.20(14) . . . . ?
N3 S1 N4 C18 0.14(13) . . . . ?
C15 N1 C1 C14 -0.61(16) . . . . ?
C28 N1 C1 C14 -161.46(13) . . . . ?
C15 N1 C1 C2 179.20(15) . . . . ?
C28 N1 C1 C2 18.4(2) . . . . ?
C14 C1 C2 C3 -173.18(15) . . . . ?
N1 C1 C2 C3 7.0(3) . . . . ?
C14 C1 C2 C7 5.6(2) . . . . ?
N1 C1 C2 C7 -174.19(15) . . . . ?
C7 C2 C3 C4 2.0(3) . . . . ?
C1 C2 C3 C4 -179.22(16) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C5 C6 C7 C2 1.0(3) . . . . ?
C5 C6 C7 C8 -179.18(18) . . . . ?
C3 C2 C7 C6 -2.4(2) . . . . ?
C1 C2 C7 C6 178.75(14) . . . . ?
C3 C2 C7 C8 177.76(14) . . . . ?
C1 C2 C7 C8 -1.1(2) . . . . ?
C6 C7 C8 C9 -6.1(2) . . . . ?
C2 C7 C8 C9 173.70(14) . . . . ?
C6 C7 C8 C13 177.57(15) . . . . ?
C2 C7 C8 C13 -2.6(2) . . . . ?
C13 C8 C9 C10 1.7(2) . . . . ?
C7 C8 C9 C10 -174.67(15) . . . . ?
C8 C9 C10 C11 -2.3(3) . . . . ?
C9 C10 C11 C12 1.1(3) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C11 C12 C13 C8 -1.1(2) . . . . ?
C11 C12 C13 C14 173.07(16) . . . . ?
C9 C8 C13 C12 -0.1(2) . . . . ?
C7 C8 C13 C12 176.43(14) . . . . ?
C9 C8 C13 C14 -174.44(13) . . . . ?
C7 C8 C13 C14 2.1(2) . . . . ?
N1 C1 C14 N2 -0.13(17) . . . . ?
C2 C1 C14 N2 -179.96(13) . . . . ?
N1 C1 C14 C13 173.45(13) . . . . ?
C2 C1 C14 C13 -6.4(2) . . . . ?
C15 N2 C14 C1 0.85(17) . . . . ?
C15 N2 C14 C13 -172.34(15) . . . . ?
C12 C13 C14 C1 -172.05(15) . . . . ?
C8 C13 C14 C1 2.3(2) . . . . ?
C12 C13 C14 N2 0.5(2) . . . . ?
C8 C13 C14 N2 174.84(14) . . . . ?
C14 N2 C15 N1 -1.27(17) . . . . ?
C14 N2 C15 C16 176.20(14) . . . . ?
C1 N1 C15 N2 1.23(17) . . . . ?
C28 N1 C15 N2 162.15(13) . . . . ?
C1 N1 C15 C16 -176.31(14) . . . . ?
C28 N1 C15 C16 -15.4(2) . . . . ?
N2 C15 C16 C21 123.22(17) . . . . ?
N1 C15 C16 C21 -59.5(2) . . . . ?
N2 C15 C16 C17 -56.8(2) . . . . ?
N1 C15 C16 C17 120.42(16) . . . . ?
S1 N3 C17 C16 179.02(12) . . . . ?
S1 N3 C17 C18 -0.47(16) . . . . ?
C21 C16 C17 N3 -179.79(15) . . . . ?
C15 C16 C17 N3 0.2(2) . . . . ?
C21 C16 C17 C18 -0.3(2) . . . . ?
C15 C16 C17 C18 179.70(13) . . . . ?
S1 N4 C18 C19 -179.11(12) . . . . ?
S1 N4 C18 C17 -0.43(16) . . . . ?
N3 C17 C18 N4 0.62(19) . . . . ?
C16 C17 C18 N4 -178.90(13) . . . . ?
N3 C17 C18 C19 179.37(13) . . . . ?
C16 C17 C18 C19 -0.1(2) . . . . ?
N4 C18 C19 C20 179.73(14) . . . . ?
C17 C18 C19 C20 1.2(2) . . . . ?
N4 C18 C19 C22 1.1(2) . . . . ?
C17 C18 C19 C22 -177.43(13) . . . . ?
C18 C19 C20 C21 -1.7(2) . . . . ?
C22 C19 C20 C21 176.85(13) . . . . ?
C17 C16 C21 C20 -0.2(2) . . . . ?
C15 C16 C21 C20 179.74(14) . . . . ?
C19 C20 C21 C16 1.4(2) . . . . ?
C20 C19 C22 C27 -25.1(2) . . . . ?
C18 C19 C22 C27 153.41(17) . . . . ?
C20 C19 C22 C23 155.01(15) . . . . ?
C18 C19 C22 C23 -26.5(2) . . . . ?
C27 C22 C23 C24 1.1(2) . . . . ?
C19 C22 C23 C24 -178.94(15) . . . . ?
C22 C23 C24 C25 0.3(3) . . . . ?
C23 C24 C25 C26 -1.8(3) . . . . ?
C24 C25 C26 C27 1.7(4) . . . . ?
C25 C26 C27 C22 -0.2(4) . . . . ?
C23 C22 C27 C26 -1.2(3) . . . . ?
C19 C22 C27 C26 178.9(2) . . . . ?
C15 N1 C28 C29 87.76(19) . . . . ?
C1 N1 C28 C29 -115.00(17) . . . . ?
C15 N1 C28 C33 -92.95(18) . . . . ?
C1 N1 C28 C33 64.3(2) . . . . ?
C33 C28 C29 C30 0.9(2) . . . . ?
N1 C28 C29 C30 -179.79(14) . . . . ?
C28 C29 C30 C31 -0.6(3) . . . . ?
C29 C30 C31 C32 -0.4(3) . . . . ?
C29 C30 C31 C34 -179.36(17) . . . . ?
C30 C31 C32 C33 1.1(3) . . . . ?
C34 C31 C32 C33 -179.94(17) . . . . ?
C29 C28 C33 C32 -0.2(2) . . . . ?
N1 C28 C33 C32 -179.54(14) . . . . ?
C31 C32 C33 C28 -0.8(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
#==============================================================================
_chemical_name_systematic        
4-Phenyl-7-[1-(p-tolyl)-1H-phenanthro[9,10-d]imidazol-2-yl]benzo[c][1,2,5]thiadiazole
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform/hexane'
_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_sta254
_database_code_depnum_ccdc_archive 'CCDC 1995253'
loop_
_audit_author_name
_audit_author_address
'Suguru Ito'
;Yokohama National University
Japan
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-01 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C33 H19 Br N4 S'
_chemical_formula_moiety         'C33 H19 Br N4 S'
_chemical_formula_weight         583.50
_chemical_melting_point          545.75-548.55

#==============================================================================
# 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                   10.39805(19)
_cell_length_b                   18.2187(4)
_cell_length_c                   13.3287(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.0879(17)
_cell_angle_gamma                90.0000
_cell_volume                     2521.31(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10229
_cell_measurement_theta_min      4.12
_cell_measurement_theta_max      74.75
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.289
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.161
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1184.00
_exptl_absorpt_coefficient_mu    3.244
_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  0.262
_exptl_absorpt_correction_T_max  0.593

#==============================================================================
# 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            17435
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_theta_max         68.218
_diffrn_reflns_theta_min         4.114
_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       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4612
_reflns_number_gt                4138
_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          0.0577
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1569
_refine_ls_wR_factor_gt          0.1535
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4612
_refine_ls_number_parameters     352
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0951P)²+2.1532P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.83
_refine_diff_density_min         -1.15
_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)
;
Br Br -0.6763 1.2805
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.41100(4) 0.20283(2) 1.11332(3) 0.05468(18) Uani 1 1 d . . . . .
S1 S 0.32603(7) 0.02430(5) 0.65914(6) 0.0425(2) Uani 1 1 d . . . . .
N1 N 0.1953(2) 0.16070(14) 0.95690(18) 0.0320(5) Uani 1 1 d . . . . .
N2 N 0.1587(2) 0.26015(14) 0.86122(17) 0.0326(5) Uani 1 1 d . . . . .
N3 N 0.2679(2) 0.08106(15) 0.73756(19) 0.0372(6) Uani 1 1 d . . . . .
N4 N 0.4699(2) 0.05525(15) 0.65104(19) 0.0363(6) Uani 1 1 d . . . . .
C1 C 0.0812(3) 0.19133(16) 0.9870(2) 0.0300(6) Uani 1 1 d . . . . .
C2 C -0.0029(3) 0.17003(17) 1.0641(2) 0.0317(6) Uani 1 1 d . . . . .
C3 C 0.0217(3) 0.11255(18) 1.1325(2) 0.0408(7) Uani 1 1 d . . . . .
H3 H 0.0980 0.0852 1.1297 0.049 Uiso 1 1 calc R U . . .
C4 C -0.0653(4) 0.09567(19) 1.2043(3) 0.0462(8) Uani 1 1 d . . . . .
H4 H -0.0486 0.0567 1.2493 0.055 Uiso 1 1 calc R U . . .
C5 C -0.1771(3) 0.13664(19) 1.2093(2) 0.0447(8) Uani 1 1 d . . . . .
H5 H -0.2361 0.1251 1.2579 0.054 Uiso 1 1 calc R U . . .
C6 C -0.2026(3) 0.19343(17) 1.1446(2) 0.0381(7) Uani 1 1 d . . . . .
H6 H -0.2790 0.2204 1.1501 0.046 Uiso 1 1 calc R U . . .
C7 C -0.1179(3) 0.21301(16) 1.0693(2) 0.0320(6) Uani 1 1 d . . . . .
C8 C -0.1433(3) 0.27517(17) 1.0028(2) 0.0311(6) Uani 1 1 d . . . . .
C9 C -0.2570(3) 0.31763(19) 1.0040(2) 0.0393(7) Uani 1 1 d . . . . .
H9 H -0.3206 0.3048 1.0483 0.047 Uiso 1 1 calc R U . . .
C10 C -0.2769(3) 0.3771(2) 0.9419(3) 0.0455(8) Uani 1 1 d . . . . .
H10 H -0.3543 0.4036 0.9437 0.055 Uiso 1 1 calc R U . . .
C11 C -0.1847(3) 0.3989(2) 0.8765(3) 0.0455(8) Uani 1 1 d . . . . .
H11 H -0.1979 0.4408 0.8361 0.055 Uiso 1 1 calc R U . . .
C12 C -0.0735(3) 0.35824(18) 0.8717(2) 0.0390(7) Uani 1 1 d . . . . .
H12 H -0.0112 0.3723 0.8268 0.047 Uiso 1 1 calc R U . . .
C13 C -0.0520(3) 0.29660(15) 0.9323(2) 0.0304(6) Uani 1 1 d . . . . .
C14 C 0.0606(3) 0.25156(16) 0.9269(2) 0.0295(6) Uani 1 1 d . . . . .
C15 C 0.2370(3) 0.20516(16) 0.8815(2) 0.0317(6) Uani 1 1 d . . . . .
C16 C 0.3562(3) 0.18887(16) 0.8300(2) 0.0310(6) Uani 1 1 d . . . . .
C17 C 0.3635(2) 0.12946(16) 0.7616(2) 0.0303(6) Uani 1 1 d . . . . .
C18 C 0.4795(3) 0.11465(16) 0.7111(2) 0.0303(6) Uani 1 1 d . . . . .
C19 C 0.5925(2) 0.15818(17) 0.7305(2) 0.0312(6) Uani 1 1 d . . . . .
C20 C 0.5804(3) 0.21576(17) 0.7950(2) 0.0352(6) Uani 1 1 d . . . . .
H20 H 0.6518 0.2467 0.8077 0.042 Uiso 1 1 calc R U . . .
C21 C 0.4652(3) 0.23141(17) 0.8441(2) 0.0348(6) Uani 1 1 d . . . . .
H21 H 0.4635 0.2720 0.8876 0.042 Uiso 1 1 calc R U . . .
C22 C 0.7177(3) 0.13734(17) 0.6898(2) 0.0335(6) Uani 1 1 d . . . . .
C23 C 0.7272(3) 0.11414(18) 0.5916(2) 0.0400(7) Uani 1 1 d . . . . .
H23 H 0.6534 0.1124 0.5477 0.048 Uiso 1 1 calc R U . . .
C24 C 0.8463(3) 0.0934(2) 0.5581(3) 0.0470(8) Uani 1 1 d . . . . .
H24 H 0.8531 0.0778 0.4914 0.056 Uiso 1 1 calc R U . . .
C25 C 0.9541(3) 0.0957(2) 0.6225(3) 0.0470(8) Uani 1 1 d . . . . .
H25 H 1.0341 0.0814 0.5993 0.056 Uiso 1 1 calc R U . . .
C26 C 0.9464(3) 0.1183(2) 0.7194(3) 0.0473(8) Uani 1 1 d . . . . .
H26 H 1.0208 0.1195 0.7627 0.057 Uiso 1 1 calc R U . . .
C27 C 0.8281(3) 0.13960(19) 0.7543(2) 0.0406(7) Uani 1 1 d . . . . .
H27 H 0.8227 0.1555 0.8210 0.049 Uiso 1 1 calc R U . . .
C28 C 0.2621(3) 0.09849(17) 0.9983(2) 0.0334(6) Uani 1 1 d . . . . .
C29 C 0.3631(3) 0.10792(18) 1.0701(2) 0.0387(7) Uani 1 1 d . . . . .
C30 C 0.4253(4) 0.0465(2) 1.1124(2) 0.0502(9) Uani 1 1 d . . . . .
H30 H 0.4938 0.0521 1.1607 0.060 Uiso 1 1 calc R U . . .
C31 C 0.3851(4) -0.0223(2) 1.0825(3) 0.0584(10) Uani 1 1 d . . . . .
H31 H 0.4267 -0.0637 1.1109 0.070 Uiso 1 1 calc R U . . .
C32 C 0.2853(4) -0.0317(2) 1.0120(3) 0.0548(9) Uani 1 1 d . . . . .
H32 H 0.2592 -0.0793 0.9928 0.066 Uiso 1 1 calc R U . . .
C33 C 0.2236(4) 0.02788(19) 0.9694(2) 0.0453(8) Uani 1 1 d . . . . .
H33 H 0.1556 0.0213 0.9208 0.054 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
Br1 C29 1.881(3) . ?
S1 N4 1.608(2) . ?
S1 N3 1.611(3) . ?
N1 C15 1.379(4) . ?
N1 C1 1.390(3) . ?
N1 C28 1.425(4) . ?
N2 C15 1.310(4) . ?
N2 C14 1.388(3) . ?
N3 C17 1.354(4) . ?
N4 C18 1.347(4) . ?
C1 C14 1.369(4) . ?
C1 C2 1.438(4) . ?
C2 C3 1.403(4) . ?
C2 C7 1.434(4) . ?
C3 C4 1.386(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.386(5) . ?
C4 H4 0.9400 . ?
C5 C6 1.364(5) . ?
C5 H5 0.9400 . ?
C6 C7 1.416(4) . ?
C6 H6 0.9400 . ?
C7 C8 1.454(4) . ?
C8 C9 1.414(4) . ?
C8 C13 1.426(4) . ?
C9 C10 1.373(5) . ?
C9 H9 0.9400 . ?
C10 C11 1.387(5) . ?
C10 H10 0.9400 . ?
C11 C12 1.377(5) . ?
C11 H11 0.9400 . ?
C12 C13 1.394(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.435(4) . ?
C15 C16 1.479(4) . ?
C16 C21 1.378(4) . ?
C16 C17 1.420(4) . ?
C17 C18 1.438(4) . ?
C18 C19 1.430(4) . ?
C19 C20 1.367(4) . ?
C19 C22 1.486(4) . ?
C20 C21 1.424(4) . ?
C20 H20 0.9400 . ?
C21 H21 0.9400 . ?
C22 C23 1.384(4) . ?
C22 C27 1.397(4) . ?
C23 C24 1.392(4) . ?
C23 H23 0.9400 . ?
C24 C25 1.375(5) . ?
C24 H24 0.9400 . ?
C25 C26 1.363(5) . ?
C25 H25 0.9400 . ?
C26 C27 1.392(4) . ?
C26 H26 0.9400 . ?
C27 H27 0.9400 . ?
C28 C29 1.393(4) . ?
C28 C33 1.396(5) . ?
C29 C30 1.396(5) . ?
C30 C31 1.373(6) . ?
C30 H30 0.9400 . ?
C31 C32 1.373(6) . ?
C31 H31 0.9400 . ?
C32 C33 1.368(5) . ?
C32 H32 0.9400 . ?
C33 H33 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 101.61(13) . . ?
C15 N1 C1 106.3(2) . . ?
C15 N1 C28 125.8(2) . . ?
C1 N1 C28 127.8(2) . . ?
C15 N2 C14 104.7(2) . . ?
C17 N3 S1 105.99(19) . . ?
C18 N4 S1 106.33(19) . . ?
C14 C1 N1 105.2(2) . . ?
C14 C1 C2 123.5(3) . . ?
N1 C1 C2 131.2(3) . . ?
C3 C2 C7 119.9(3) . . ?
C3 C2 C1 124.7(3) . . ?
C7 C2 C1 115.4(3) . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 122.1(3) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C6 C7 C2 116.7(3) . . ?
C6 C7 C8 121.9(3) . . ?
C2 C7 C8 121.3(2) . . ?
C9 C8 C13 116.4(3) . . ?
C9 C8 C7 123.0(3) . . ?
C13 C8 C7 120.7(3) . . ?
C10 C9 C8 121.6(3) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 121.2(3) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 119.1(3) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 121.0(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C8 120.7(3) . . ?
C12 C13 C14 122.5(3) . . ?
C8 C13 C14 116.8(3) . . ?
C1 C14 N2 111.2(2) . . ?
C1 C14 C13 122.1(2) . . ?
N2 C14 C13 126.6(3) . . ?
N2 C15 N1 112.6(2) . . ?
N2 C15 C16 125.8(3) . . ?
N1 C15 C16 121.6(2) . . ?
C21 C16 C17 116.4(2) . . ?
C21 C16 C15 121.8(3) . . ?
C17 C16 C15 121.7(3) . . ?
N3 C17 C16 125.8(2) . . ?
N3 C17 C18 113.0(3) . . ?
C16 C17 C18 121.2(2) . . ?
N4 C18 C19 125.9(2) . . ?
N4 C18 C17 113.1(2) . . ?
C19 C18 C17 120.9(3) . . ?
C20 C19 C18 115.9(2) . . ?
C20 C19 C22 122.5(3) . . ?
C18 C19 C22 121.4(3) . . ?
C19 C20 C21 123.5(3) . . ?
C19 C20 H20 118.3 . . ?
C21 C20 H20 118.3 . . ?
C16 C21 C20 122.0(3) . . ?
C16 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C23 C22 C27 119.5(3) . . ?
C23 C22 C19 122.1(3) . . ?
C27 C22 C19 118.4(3) . . ?
C22 C23 C24 119.7(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 120.1(3) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C26 C25 C24 120.9(3) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 119.9(3) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C26 C27 C22 119.9(3) . . ?
C26 C27 H27 120.1 . . ?
C22 C27 H27 120.1 . . ?
C29 C28 C33 119.9(3) . . ?
C29 C28 N1 120.1(3) . . ?
C33 C28 N1 120.0(3) . . ?
C28 C29 C30 119.6(3) . . ?
C28 C29 Br1 120.1(2) . . ?
C30 C29 Br1 120.3(3) . . ?
C31 C30 C29 119.1(3) . . ?
C31 C30 H30 120.4 . . ?
C29 C30 H30 120.4 . . ?
C30 C31 C32 121.3(3) . . ?
C30 C31 H31 119.3 . . ?
C32 C31 H31 119.3 . . ?
C33 C32 C31 120.3(4) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C32 C33 C28 119.7(3) . . ?
C32 C33 H33 120.1 . . ?
C28 C33 H33 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 S1 N3 C17 0.4(2) . . . . ?
N3 S1 N4 C18 -0.7(2) . . . . ?
C15 N1 C1 C14 0.8(3) . . . . ?
C28 N1 C1 C14 177.4(3) . . . . ?
C15 N1 C1 C2 -178.1(3) . . . . ?
C28 N1 C1 C2 -1.5(5) . . . . ?
C14 C1 C2 C3 -174.1(3) . . . . ?
N1 C1 C2 C3 4.7(5) . . . . ?
C14 C1 C2 C7 4.9(4) . . . . ?
N1 C1 C2 C7 -176.3(3) . . . . ?
C7 C2 C3 C4 1.3(5) . . . . ?
C1 C2 C3 C4 -179.7(3) . . . . ?
C2 C3 C4 C5 -0.8(5) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C4 C5 C6 C7 0.5(5) . . . . ?
C5 C6 C7 C2 0.0(4) . . . . ?
C5 C6 C7 C8 -177.8(3) . . . . ?
C3 C2 C7 C6 -0.9(4) . . . . ?
C1 C2 C7 C6 -180.0(3) . . . . ?
C3 C2 C7 C8 177.0(3) . . . . ?
C1 C2 C7 C8 -2.1(4) . . . . ?
C6 C7 C8 C9 -3.9(4) . . . . ?
C2 C7 C8 C9 178.3(3) . . . . ?
C6 C7 C8 C13 175.7(3) . . . . ?
C2 C7 C8 C13 -2.0(4) . . . . ?
C13 C8 C9 C10 -1.3(5) . . . . ?
C7 C8 C9 C10 178.4(3) . . . . ?
C8 C9 C10 C11 -1.2(5) . . . . ?
C9 C10 C11 C12 2.3(5) . . . . ?
C10 C11 C12 C13 -0.9(5) . . . . ?
C11 C12 C13 C8 -1.6(5) . . . . ?
C11 C12 C13 C14 177.8(3) . . . . ?
C9 C8 C13 C12 2.7(4) . . . . ?
C7 C8 C13 C12 -177.0(3) . . . . ?
C9 C8 C13 C14 -176.8(3) . . . . ?
C7 C8 C13 C14 3.5(4) . . . . ?
N1 C1 C14 N2 -0.8(3) . . . . ?
C2 C1 C14 N2 178.2(3) . . . . ?
N1 C1 C14 C13 177.4(3) . . . . ?
C2 C1 C14 C13 -3.6(5) . . . . ?
C15 N2 C14 C1 0.4(3) . . . . ?
C15 N2 C14 C13 -177.7(3) . . . . ?
C12 C13 C14 C1 179.7(3) . . . . ?
C8 C13 C14 C1 -0.8(4) . . . . ?
C12 C13 C14 N2 -2.4(5) . . . . ?
C8 C13 C14 N2 177.1(3) . . . . ?
C14 N2 C15 N1 0.1(3) . . . . ?
C14 N2 C15 C16 178.7(3) . . . . ?
C1 N1 C15 N2 -0.6(3) . . . . ?
C28 N1 C15 N2 -177.3(3) . . . . ?
C1 N1 C15 C16 -179.2(3) . . . . ?
C28 N1 C15 C16 4.1(5) . . . . ?
N2 C15 C16 C21 72.0(4) . . . . ?
N1 C15 C16 C21 -109.5(3) . . . . ?
N2 C15 C16 C17 -106.6(4) . . . . ?
N1 C15 C16 C17 71.8(4) . . . . ?
S1 N3 C17 C16 -178.9(2) . . . . ?
S1 N3 C17 C18 0.1(3) . . . . ?
C21 C16 C17 N3 179.6(3) . . . . ?
C15 C16 C17 N3 -1.7(4) . . . . ?
C21 C16 C17 C18 0.6(4) . . . . ?
C15 C16 C17 C18 179.3(3) . . . . ?
S1 N4 C18 C19 177.3(2) . . . . ?
S1 N4 C18 C17 0.8(3) . . . . ?
N3 C17 C18 N4 -0.6(3) . . . . ?
C16 C17 C18 N4 178.5(3) . . . . ?
N3 C17 C18 C19 -177.3(2) . . . . ?
C16 C17 C18 C19 1.7(4) . . . . ?
N4 C18 C19 C20 -179.4(3) . . . . ?
C17 C18 C19 C20 -3.1(4) . . . . ?
N4 C18 C19 C22 -4.8(4) . . . . ?
C17 C18 C19 C22 171.5(3) . . . . ?
C18 C19 C20 C21 2.2(4) . . . . ?
C22 C19 C20 C21 -172.3(3) . . . . ?
C17 C16 C21 C20 -1.6(4) . . . . ?
C15 C16 C21 C20 179.7(3) . . . . ?
C19 C20 C21 C16 0.1(5) . . . . ?
C20 C19 C22 C23 -141.3(3) . . . . ?
C18 C19 C22 C23 44.5(4) . . . . ?
C20 C19 C22 C27 40.4(4) . . . . ?
C18 C19 C22 C27 -133.8(3) . . . . ?
C27 C22 C23 C24 0.0(5) . . . . ?
C19 C22 C23 C24 -178.3(3) . . . . ?
C22 C23 C24 C25 0.3(5) . . . . ?
C23 C24 C25 C26 -0.2(6) . . . . ?
C24 C25 C26 C27 -0.1(6) . . . . ?
C25 C26 C27 C22 0.3(5) . . . . ?
C23 C22 C27 C26 -0.3(5) . . . . ?
C19 C22 C27 C26 178.1(3) . . . . ?
C15 N1 C28 C29 80.2(4) . . . . ?
C1 N1 C28 C29 -95.8(4) . . . . ?
C15 N1 C28 C33 -101.9(4) . . . . ?
C1 N1 C28 C33 82.2(4) . . . . ?
C33 C28 C29 C30 0.2(5) . . . . ?
N1 C28 C29 C30 178.1(3) . . . . ?
C33 C28 C29 Br1 -177.5(2) . . . . ?
N1 C28 C29 Br1 0.4(4) . . . . ?
C28 C29 C30 C31 -0.3(5) . . . . ?
Br1 C29 C30 C31 177.4(3) . . . . ?
C29 C30 C31 C32 0.1(6) . . . . ?
C30 C31 C32 C33 0.3(6) . . . . ?
C31 C32 C33 C28 -0.3(6) . . . . ?
C29 C28 C33 C32 0.1(5) . . . . ?
N1 C28 C33 C32 -177.8(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
#==============================================================================
_chemical_name_systematic        
4-[1-(2-Bromophenyl)-1H-phenanthro[9,10-d]imidazol-2-yl]-7-phenylbenzo[c][1,2,5]thiadiazole
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform/hexane'
_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_sta251
_database_code_depnum_ccdc_archive 'CCDC 1995251'
loop_
_audit_author_name
_audit_author_address
'Suguru Ito'
;Yokohama National University
Japan
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-01 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C34 H19 F3 N4 S'
_chemical_formula_moiety         'C34 H19 F3 N4 S'
_chemical_formula_weight         572.61
_chemical_melting_point          496.75-499.55

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.7391(3)
_cell_length_b                   13.8406(5)
_cell_length_c                   15.2075(5)
_cell_angle_alpha                113.486(3)
_cell_angle_beta                 90.031(3)
_cell_angle_gamma                96.987(3)
_cell_volume                     1289.41(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6705
_cell_measurement_theta_min      5.89
_cell_measurement_theta_max      75.02
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.952
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.093
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             588.00
_exptl_absorpt_coefficient_mu    1.586
_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  0.576
_exptl_absorpt_correction_T_max  0.863

#==============================================================================
# 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            12728
_diffrn_reflns_av_R_equivalents  0.1047
_diffrn_reflns_theta_max         68.245
_diffrn_reflns_theta_min         3.669
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4685
_reflns_number_gt                3733
_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          0.0794
_refine_ls_R_factor_gt           0.0695
_refine_ls_wR_factor_ref         0.2109
_refine_ls_wR_factor_gt          0.1973
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4685
_refine_ls_number_parameters     379
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1420P)²] 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         0.59
_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)
;
S S 0.3331 0.5567
;
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)
;

#==============================================================================
# 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 0.49113(10) 0.34837(5) 0.44453(5) 0.0536(3) Uani 1 1 d . . . . .
F1 F -0.6195(2) 0.12902(16) 0.07419(14) 0.0659(5) Uani 1 1 d . . . . .
F2 F -0.3668(3) 0.13714(17) -0.00795(13) 0.0704(6) Uani 1 1 d . . . . .
F3 F -0.3993(3) 0.26536(14) 0.12520(16) 0.0765(6) Uani 1 1 d . . . . .
N1 N 0.0175(3) -0.02751(15) 0.27707(14) 0.0369(5) Uani 1 1 d . . . . .
N2 N 0.2681(3) -0.01903(16) 0.37831(15) 0.0428(5) Uani 1 1 d . . . . .
N3 N 0.3900(3) 0.22609(17) 0.40465(16) 0.0469(5) Uani 1 1 d . . . . .
N4 N 0.3252(3) 0.40673(17) 0.51399(17) 0.0458(5) Uani 1 1 d . . . . .
C1 C 0.1092(3) -0.11875(18) 0.23229(18) 0.0380(5) Uani 1 1 d . . . . .
C2 C 0.0629(4) -0.20680(18) 0.14180(18) 0.0405(6) Uani 1 1 d . . . . .
C3 C -0.1028(4) -0.2199(2) 0.0795(2) 0.0477(6) Uani 1 1 d . . . . .
H3 H -0.1922 -0.1691 0.0974 0.057 Uiso 1 1 calc R U . . .
C4 C -0.1353(5) -0.3057(2) -0.0069(2) 0.0553(7) Uani 1 1 d . . . . .
H4 H -0.2462 -0.3135 -0.0478 0.066 Uiso 1 1 calc R U . . .
C5 C -0.0033(5) -0.3813(2) -0.0337(2) 0.0619(8) Uani 1 1 d . . . . .
H5 H -0.0232 -0.4392 -0.0937 0.074 Uiso 1 1 calc R U . . .
C6 C 0.1550(5) -0.3716(2) 0.0268(2) 0.0571(8) Uani 1 1 d . . . . .
H6 H 0.2406 -0.4244 0.0079 0.069 Uiso 1 1 calc R U . . .
C7 C 0.1941(4) -0.28568(19) 0.11632(19) 0.0446(6) Uani 1 1 d . . . . .
C8 C 0.3627(4) -0.2768(2) 0.1819(2) 0.0457(6) Uani 1 1 d . . . . .
C9 C 0.4986(5) -0.3519(2) 0.1584(2) 0.0567(7) Uani 1 1 d . . . . .
H9 H 0.4789 -0.4116 0.0996 0.068 Uiso 1 1 calc R U . . .
C10 C 0.6587(5) -0.3401(3) 0.2189(3) 0.0626(8) Uani 1 1 d . . . . .
H10 H 0.7475 -0.3912 0.2009 0.075 Uiso 1 1 calc R U . . .
C11 C 0.6910(5) -0.2535(3) 0.3063(3) 0.0580(8) Uani 1 1 d . . . . .
H11 H 0.8029 -0.2453 0.3468 0.070 Uiso 1 1 calc R U . . .
C12 C 0.5599(4) -0.1795(2) 0.3340(2) 0.0497(7) Uani 1 1 d . . . . .
H12 H 0.5797 -0.1219 0.3942 0.060 Uiso 1 1 calc R U . . .
C13 C 0.3955(4) -0.18987(19) 0.27213(19) 0.0429(6) Uani 1 1 d . . . . .
C14 C 0.2610(4) -0.11135(19) 0.29589(18) 0.0396(6) Uani 1 1 d . . . . .
C15 C 0.1239(4) 0.02913(19) 0.36503(18) 0.0392(6) Uani 1 1 d . . . . .
C16 C 0.0761(4) 0.13392(18) 0.43111(17) 0.0382(5) Uani 1 1 d . . . . .
C17 C 0.2155(4) 0.22712(19) 0.44713(17) 0.0383(6) Uani 1 1 d . . . . .
C18 C 0.1751(4) 0.33014(18) 0.50946(17) 0.0380(6) Uani 1 1 d . . . . .
C19 C -0.0078(3) 0.34561(19) 0.55912(16) 0.0382(6) Uani 1 1 d . . . . .
C20 C -0.1371(4) 0.2523(2) 0.54006(18) 0.0428(6) Uani 1 1 d . . . . .
H20 H -0.2597 0.2576 0.5699 0.051 Uiso 1 1 calc R U . . .
C21 C -0.0959(4) 0.1505(2) 0.47899(18) 0.0440(6) Uani 1 1 d . . . . .
H21 H -0.1908 0.0915 0.4708 0.053 Uiso 1 1 calc R U . . .
C22 C -0.0639(4) 0.45021(19) 0.62359(17) 0.0386(5) Uani 1 1 d . . . . .
C23 C 0.0424(5) 0.5463(2) 0.6297(2) 0.0565(8) Uani 1 1 d . . . . .
H23 H 0.1554 0.5448 0.5933 0.068 Uiso 1 1 calc R U . . .
C24 C -0.0142(5) 0.6427(2) 0.6878(2) 0.0585(8) Uani 1 1 d . . . . .
H24 H 0.0617 0.7057 0.6909 0.070 Uiso 1 1 calc R U . . .
C25 C -0.1789(5) 0.6481(2) 0.7409(2) 0.0554(7) Uani 1 1 d . . . . .
H25 H -0.2178 0.7141 0.7801 0.066 Uiso 1 1 calc R U . . .
C26 C -0.2870(5) 0.5544(2) 0.7357(2) 0.0637(9) Uani 1 1 d . . . . .
H26 H -0.4017 0.5568 0.7713 0.076 Uiso 1 1 calc R U . . .
C27 C -0.2290(4) 0.4578(2) 0.6792(2) 0.0543(7) Uani 1 1 d . . . . .
H27 H -0.3033 0.3953 0.6782 0.065 Uiso 1 1 calc R U . . .
C28 C -0.0983(3) 0.01944(17) 0.22915(17) 0.0365(5) Uani 1 1 d . . . . .
C29 C -0.0104(4) 0.04439(19) 0.15679(18) 0.0403(6) Uani 1 1 d . . . . .
H29 H 0.1209 0.0305 0.1407 0.048 Uiso 1 1 calc R U . . .
C30 C -0.1149(4) 0.0893(2) 0.10876(18) 0.0411(6) Uani 1 1 d . . . . .
H30 H -0.0553 0.1062 0.0599 0.049 Uiso 1 1 calc R U . . .
C31 C -0.3088(4) 0.10987(18) 0.13251(17) 0.0385(5) Uani 1 1 d . . . . .
C32 C -0.3955(4) 0.0861(2) 0.20578(18) 0.0424(6) Uani 1 1 d . . . . .
H32 H -0.5260 0.1011 0.2225 0.051 Uiso 1 1 calc R U . . .
C33 C -0.2912(4) 0.0410(2) 0.25366(18) 0.0422(6) Uani 1 1 d . . . . .
H33 H -0.3503 0.0247 0.3029 0.051 Uiso 1 1 calc R U . . .
C34 C -0.4221(4) 0.1599(2) 0.0814(2) 0.0467(6) 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 1.600(2) . ?
S1 N3 1.612(2) . ?
F1 C34 1.337(3) . ?
F2 C34 1.331(3) . ?
F3 C34 1.330(3) . ?
N1 C15 1.394(3) . ?
N1 C1 1.395(3) . ?
N1 C28 1.436(3) . ?
N2 C15 1.302(3) . ?
N2 C14 1.384(3) . ?
N3 C17 1.341(3) . ?
N4 C18 1.354(3) . ?
C1 C14 1.373(4) . ?
C1 C2 1.431(3) . ?
C2 C3 1.411(4) . ?
C2 C7 1.422(4) . ?
C3 C4 1.369(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.392(5) . ?
C4 H4 0.9400 . ?
C5 C6 1.367(5) . ?
C5 H5 0.9400 . ?
C6 C7 1.403(4) . ?
C6 H6 0.9400 . ?
C7 C8 1.472(4) . ?
C8 C9 1.408(4) . ?
C8 C13 1.414(4) . ?
C9 C10 1.369(5) . ?
C9 H9 0.9400 . ?
C10 C11 1.385(5) . ?
C10 H10 0.9400 . ?
C11 C12 1.373(4) . ?
C11 H11 0.9400 . ?
C12 C13 1.408(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.436(4) . ?
C15 C16 1.473(3) . ?
C16 C21 1.363(4) . ?
C16 C17 1.435(3) . ?
C17 C18 1.422(3) . ?
C18 C19 1.440(3) . ?
C19 C20 1.393(3) . ?
C19 C22 1.484(3) . ?
C20 C21 1.406(4) . ?
C20 H20 0.9400 . ?
C21 H21 0.9400 . ?
C22 C27 1.386(4) . ?
C22 C23 1.400(4) . ?
C23 C24 1.375(4) . ?
C23 H23 0.9400 . ?
C24 C25 1.365(4) . ?
C24 H24 0.9400 . ?
C25 C26 1.380(4) . ?
C25 H25 0.9400 . ?
C26 C27 1.375(4) . ?
C26 H26 0.9400 . ?
C27 H27 0.9400 . ?
C28 C33 1.387(4) . ?
C28 C29 1.391(3) . ?
C29 C30 1.373(4) . ?
C29 H29 0.9400 . ?
C30 C31 1.388(3) . ?
C30 H30 0.9400 . ?
C31 C32 1.392(3) . ?
C31 C34 1.492(4) . ?
C32 C33 1.372(4) . ?
C32 H32 0.9400 . ?
C33 H33 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 101.22(11) . . ?
C15 N1 C1 105.5(2) . . ?
C15 N1 C28 124.18(19) . . ?
C1 N1 C28 125.59(19) . . ?
C15 N2 C14 105.1(2) . . ?
C17 N3 S1 105.66(17) . . ?
C18 N4 S1 106.81(17) . . ?
C14 C1 N1 105.4(2) . . ?
C14 C1 C2 123.8(2) . . ?
N1 C1 C2 130.8(2) . . ?
C3 C2 C7 119.6(2) . . ?
C3 C2 C1 124.4(2) . . ?
C7 C2 C1 116.0(2) . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 122.3(3) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C6 C7 C2 117.2(3) . . ?
C6 C7 C8 122.0(3) . . ?
C2 C7 C8 120.9(2) . . ?
C9 C8 C13 117.0(3) . . ?
C9 C8 C7 122.6(3) . . ?
C13 C8 C7 120.4(2) . . ?
C10 C9 C8 121.7(3) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 120.6(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C8 120.6(2) . . ?
C12 C13 C14 121.8(2) . . ?
C8 C13 C14 117.6(2) . . ?
C1 C14 N2 111.3(2) . . ?
C1 C14 C13 121.3(2) . . ?
N2 C14 C13 127.4(2) . . ?
N2 C15 N1 112.7(2) . . ?
N2 C15 C16 125.9(2) . . ?
N1 C15 C16 121.3(2) . . ?
C21 C16 C17 116.0(2) . . ?
C21 C16 C15 124.6(2) . . ?
C17 C16 C15 119.5(2) . . ?
N3 C17 C18 114.3(2) . . ?
N3 C17 C16 124.1(2) . . ?
C18 C17 C16 121.6(2) . . ?
N4 C18 C17 112.0(2) . . ?
N4 C18 C19 126.6(2) . . ?
C17 C18 C19 121.4(2) . . ?
C20 C19 C18 114.2(2) . . ?
C20 C19 C22 120.8(2) . . ?
C18 C19 C22 125.0(2) . . ?
C19 C20 C21 124.2(2) . . ?
C19 C20 H20 117.9 . . ?
C21 C20 H20 117.9 . . ?
C16 C21 C20 122.7(2) . . ?
C16 C21 H21 118.7 . . ?
C20 C21 H21 118.7 . . ?
C27 C22 C23 116.3(2) . . ?
C27 C22 C19 121.5(2) . . ?
C23 C22 C19 122.2(2) . . ?
C24 C23 C22 121.7(3) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C25 C24 C23 120.9(3) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C24 C25 C26 118.5(3) . . ?
C24 C25 H25 120.7 . . ?
C26 C25 H25 120.7 . . ?
C27 C26 C25 120.8(3) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C22 121.7(3) . . ?
C26 C27 H27 119.1 . . ?
C22 C27 H27 119.1 . . ?
C33 C28 C29 120.0(2) . . ?
C33 C28 N1 122.1(2) . . ?
C29 C28 N1 117.9(2) . . ?
C30 C29 C28 120.2(2) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C31 119.9(2) . . ?
C29 C30 H30 120.1 . . ?
C31 C30 H30 120.1 . . ?
C30 C31 C32 119.9(2) . . ?
C30 C31 C34 120.1(2) . . ?
C32 C31 C34 120.0(2) . . ?
C33 C32 C31 120.2(2) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C32 C33 C28 119.8(2) . . ?
C32 C33 H33 120.1 . . ?
C28 C33 H33 120.1 . . ?
F3 C34 F2 106.2(2) . . ?
F3 C34 F1 105.6(2) . . ?
F2 C34 F1 106.0(2) . . ?
F3 C34 C31 112.7(2) . . ?
F2 C34 C31 112.8(2) . . ?
F1 C34 C31 112.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 S1 N3 C17 -0.5(2) . . . . ?
N3 S1 N4 C18 0.0(2) . . . . ?
C15 N1 C1 C14 0.6(2) . . . . ?
C28 N1 C1 C14 156.9(2) . . . . ?
C15 N1 C1 C2 178.7(2) . . . . ?
C28 N1 C1 C2 -24.9(4) . . . . ?
C14 C1 C2 C3 174.3(2) . . . . ?
N1 C1 C2 C3 -3.5(4) . . . . ?
C14 C1 C2 C7 -4.5(3) . . . . ?
N1 C1 C2 C7 177.6(2) . . . . ?
C7 C2 C3 C4 -2.3(4) . . . . ?
C1 C2 C3 C4 178.9(2) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 1.8(5) . . . . ?
C4 C5 C6 C7 -1.3(5) . . . . ?
C5 C6 C7 C2 -0.9(4) . . . . ?
C5 C6 C7 C8 178.9(3) . . . . ?
C3 C2 C7 C6 2.7(4) . . . . ?
C1 C2 C7 C6 -178.5(2) . . . . ?
C3 C2 C7 C8 -177.1(2) . . . . ?
C1 C2 C7 C8 1.8(3) . . . . ?
C6 C7 C8 C9 1.8(4) . . . . ?
C2 C7 C8 C9 -178.5(2) . . . . ?
C6 C7 C8 C13 -179.0(2) . . . . ?
C2 C7 C8 C13 0.7(4) . . . . ?
C13 C8 C9 C10 -1.7(4) . . . . ?
C7 C8 C9 C10 177.6(3) . . . . ?
C8 C9 C10 C11 0.5(5) . . . . ?
C9 C10 C11 C12 1.3(5) . . . . ?
C10 C11 C12 C13 -1.9(4) . . . . ?
C11 C12 C13 C8 0.7(4) . . . . ?
C11 C12 C13 C14 -176.6(2) . . . . ?
C9 C8 C13 C12 1.0(4) . . . . ?
C7 C8 C13 C12 -178.2(2) . . . . ?
C9 C8 C13 C14 178.4(2) . . . . ?
C7 C8 C13 C14 -0.8(3) . . . . ?
N1 C1 C14 N2 -0.2(3) . . . . ?
C2 C1 C14 N2 -178.5(2) . . . . ?
N1 C1 C14 C13 -177.1(2) . . . . ?
C2 C1 C14 C13 4.7(4) . . . . ?
C15 N2 C14 C1 -0.2(3) . . . . ?
C15 N2 C14 C13 176.4(2) . . . . ?
C12 C13 C14 C1 175.6(2) . . . . ?
C8 C13 C14 C1 -1.8(3) . . . . ?
C12 C13 C14 N2 -0.7(4) . . . . ?
C8 C13 C14 N2 -178.0(2) . . . . ?
C14 N2 C15 N1 0.6(3) . . . . ?
C14 N2 C15 C16 -177.0(2) . . . . ?
C1 N1 C15 N2 -0.8(3) . . . . ?
C28 N1 C15 N2 -157.6(2) . . . . ?
C1 N1 C15 C16 176.9(2) . . . . ?
C28 N1 C15 C16 20.2(3) . . . . ?
N2 C15 C16 C21 -114.4(3) . . . . ?
N1 C15 C16 C21 68.2(3) . . . . ?
N2 C15 C16 C17 66.5(3) . . . . ?
N1 C15 C16 C17 -110.9(3) . . . . ?
S1 N3 C17 C18 0.8(3) . . . . ?
S1 N3 C17 C16 179.6(2) . . . . ?
C21 C16 C17 N3 -178.6(2) . . . . ?
C15 C16 C17 N3 0.6(4) . . . . ?
C21 C16 C17 C18 0.1(4) . . . . ?
C15 C16 C17 C18 179.3(2) . . . . ?
S1 N4 C18 C17 0.5(3) . . . . ?
S1 N4 C18 C19 -179.0(2) . . . . ?
N3 C17 C18 N4 -0.9(3) . . . . ?
C16 C17 C18 N4 -179.7(2) . . . . ?
N3 C17 C18 C19 178.6(2) . . . . ?
C16 C17 C18 C19 -0.2(4) . . . . ?
N4 C18 C19 C20 179.2(2) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
N4 C18 C19 C22 0.9(4) . . . . ?
C17 C18 C19 C22 -178.6(2) . . . . ?
C18 C19 C20 C21 0.8(4) . . . . ?
C22 C19 C20 C21 179.2(2) . . . . ?
C17 C16 C21 C20 0.4(4) . . . . ?
C15 C16 C21 C20 -178.8(2) . . . . ?
C19 C20 C21 C16 -0.9(4) . . . . ?
C20 C19 C22 C27 10.9(4) . . . . ?
C18 C19 C22 C27 -170.9(3) . . . . ?
C20 C19 C22 C23 -167.3(3) . . . . ?
C18 C19 C22 C23 11.0(4) . . . . ?
C27 C22 C23 C24 0.0(5) . . . . ?
C19 C22 C23 C24 178.2(3) . . . . ?
C22 C23 C24 C25 -0.9(5) . . . . ?
C23 C24 C25 C26 0.5(5) . . . . ?
C24 C25 C26 C27 0.7(5) . . . . ?
C25 C26 C27 C22 -1.6(5) . . . . ?
C23 C22 C27 C26 1.2(5) . . . . ?
C19 C22 C27 C26 -177.0(3) . . . . ?
C15 N1 C28 C33 -81.5(3) . . . . ?
C1 N1 C28 C33 126.3(3) . . . . ?
C15 N1 C28 C29 97.9(3) . . . . ?
C1 N1 C28 C29 -54.3(3) . . . . ?
C33 C28 C29 C30 -0.7(3) . . . . ?
N1 C28 C29 C30 180.0(2) . . . . ?
C28 C29 C30 C31 0.0(4) . . . . ?
C29 C30 C31 C32 0.9(4) . . . . ?
C29 C30 C31 C34 179.2(2) . . . . ?
C30 C31 C32 C33 -1.0(4) . . . . ?
C34 C31 C32 C33 -179.4(2) . . . . ?
C31 C32 C33 C28 0.3(4) . . . . ?
C29 C28 C33 C32 0.5(4) . . . . ?
N1 C28 C33 C32 179.9(2) . . . . ?
C30 C31 C34 F3 -91.5(3) . . . . ?
C32 C31 C34 F3 86.9(3) . . . . ?
C30 C31 C34 F2 28.8(3) . . . . ?
C32 C31 C34 F2 -152.8(2) . . . . ?
C30 C31 C34 F1 148.9(2) . . . . ?
C32 C31 C34 F1 -32.7(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
#==============================================================================
_chemical_name_systematic        
4-Phenyl-7-{1-[4-(trifluoromethyl)phenyl]-1H-phenanthro[9,10-d]imidazol-2-yl}benzo[c][1,2,5]thiadiazole
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform/hexane'
_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_STA118
_database_code_depnum_ccdc_archive 'CCDC 1995252'
loop_
_audit_author_name
_audit_author_address
'Suguru Ito'
;Yokohama National University
Japan
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-01 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C33 H19 Br N4 S'
_chemical_formula_moiety         'C33 H19 Br N4 S'
_chemical_formula_weight         583.50
_chemical_melting_point          509.75-512.55

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.63294(10)
_cell_length_b                   13.8905(2)
_cell_length_c                   15.0996(2)
_cell_angle_alpha                66.2986(14)
_cell_angle_beta                 88.1740(12)
_cell_angle_gamma                83.1236(13)
_cell_volume                     1264.49(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9134
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      76.13
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.668
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.122
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592.00
_exptl_absorpt_coefficient_mu    3.234
_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  0.375
_exptl_absorpt_correction_T_max  0.674

#==============================================================================
# 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            14175
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_theta_max         76.493
_diffrn_reflns_theta_min         3.197
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5135
_reflns_number_gt                4535
_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          0.0541
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1436
_refine_ls_wR_factor_gt          0.1398
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5135
_refine_ls_number_parameters     352
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0753P)²+0.4562P] 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         0.53
_refine_diff_density_min         -1.04
_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)
;
Br Br -0.6763 1.2805
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.04752(5) 0.83831(3) 0.05847(2) 0.05789(15) Uani 1 1 d . . . . .
S1 S 0.99713(10) 0.64993(5) 0.44326(6) 0.0467(2) Uani 1 1 d . . . . .
N1 N 0.5314(3) 1.02220(14) 0.27553(13) 0.0308(4) Uani 1 1 d . . . . .
N2 N 0.7756(3) 1.01600(15) 0.37849(14) 0.0345(4) Uani 1 1 d . . . . .
N3 N 0.8977(3) 0.77164(17) 0.40434(16) 0.0397(5) Uani 1 1 d . . . . .
N4 N 0.8246(3) 0.59149(16) 0.51470(16) 0.0388(5) Uani 1 1 d . . . . .
C1 C 0.6258(4) 1.11416(17) 0.23071(17) 0.0314(5) Uani 1 1 d . . . . .
C2 C 0.5840(4) 1.20243(18) 0.14008(17) 0.0344(5) Uani 1 1 d . . . . .
C3 C 0.4192(4) 1.2156(2) 0.07832(19) 0.0411(6) Uani 1 1 d . . . . .
H3 H 0.3290 1.1638 0.0962 0.049 Uiso 1 1 calc R U . . .
C4 C 0.3875(6) 1.3026(2) -0.0077(2) 0.0510(7) Uani 1 1 d . . . . .
H4 H 0.2775 1.3100 -0.0486 0.061 Uiso 1 1 calc R U . . .
C5 C 0.5201(6) 1.3799(2) -0.0337(2) 0.0596(9) Uani 1 1 d . . . . .
H5 H 0.5005 1.4390 -0.0931 0.072 Uiso 1 1 calc R U . . .
C6 C 0.6781(6) 1.3706(2) 0.0261(2) 0.0536(8) Uani 1 1 d . . . . .
H6 H 0.7639 1.4243 0.0072 0.064 Uiso 1 1 calc R U . . .
C7 C 0.7170(4) 1.28275(19) 0.11545(19) 0.0392(6) Uani 1 1 d . . . . .
C8 C 0.8828(4) 1.2737(2) 0.1806(2) 0.0401(6) Uani 1 1 d . . . . .
C9 C 1.0225(5) 1.3493(2) 0.1570(2) 0.0497(7) Uani 1 1 d . . . . .
H9 H 1.0065 1.4090 0.0980 0.060 Uiso 1 1 calc R U . . .
C10 C 1.1803(5) 1.3378(3) 0.2180(3) 0.0577(8) Uani 1 1 d . . . . .
H10 H 1.2717 1.3889 0.1998 0.069 Uiso 1 1 calc R U . . .
C11 C 1.2073(5) 1.2517(3) 0.3062(2) 0.0505(7) Uani 1 1 d . . . . .
H11 H 1.3168 1.2445 0.3472 0.061 Uiso 1 1 calc R U . . .
C12 C 1.0727(4) 1.1761(2) 0.3338(2) 0.0437(6) Uani 1 1 d . . . . .
H12 H 1.0895 1.1180 0.3940 0.052 Uiso 1 1 calc R U . . .
C13 C 0.9109(4) 1.18683(19) 0.27138(19) 0.0363(5) Uani 1 1 d . . . . .
C14 C 0.7730(4) 1.10796(18) 0.29496(17) 0.0321(5) Uani 1 1 d . . . . .
C15 C 0.6305(4) 0.96706(17) 0.36440(16) 0.0312(5) Uani 1 1 d . . . . .
C16 C 0.5780(4) 0.86231(18) 0.43141(16) 0.0314(5) Uani 1 1 d . . . . .
C17 C 0.7167(4) 0.77109(18) 0.44700(16) 0.0313(5) Uani 1 1 d . . . . .
C18 C 0.6725(4) 0.66694(17) 0.51100(16) 0.0301(5) Uani 1 1 d . . . . .
C19 C 0.4838(4) 0.65251(18) 0.56170(16) 0.0307(5) Uani 1 1 d . . . . .
C20 C 0.3548(4) 0.7441(2) 0.54303(18) 0.0372(5) Uani 1 1 d . . . . .
H20 H 0.2289 0.7383 0.5740 0.045 Uiso 1 1 calc R U . . .
C21 C 0.3995(4) 0.84694(19) 0.48003(18) 0.0374(5) Uani 1 1 d . . . . .
H21 H 0.3038 0.9057 0.4717 0.045 Uiso 1 1 calc R U . . .
C22 C 0.4259(4) 0.54713(18) 0.62759(17) 0.0340(5) Uani 1 1 d . . . . .
C23 C 0.5309(5) 0.4533(2) 0.6331(3) 0.0599(9) Uani 1 1 d . . . . .
H23 H 0.6472 0.4553 0.5954 0.072 Uiso 1 1 calc R U . . .
C24 C 0.4714(6) 0.3558(2) 0.6922(3) 0.0608(9) Uani 1 1 d . . . . .
H24 H 0.5487 0.2933 0.6950 0.073 Uiso 1 1 calc R U . . .
C25 C 0.3017(5) 0.3501(2) 0.7462(2) 0.0515(7) Uani 1 1 d . . . . .
H25 H 0.2616 0.2841 0.7866 0.062 Uiso 1 1 calc R U . . .
C26 C 0.1898(5) 0.4421(3) 0.7408(2) 0.0601(9) Uani 1 1 d . . . . .
H26 H 0.0704 0.4390 0.7766 0.072 Uiso 1 1 calc R U . . .
C27 C 0.2513(5) 0.5394(2) 0.6832(2) 0.0513(7) Uani 1 1 d . . . . .
H27 H 0.1741 0.6015 0.6813 0.062 Uiso 1 1 calc R U . . .
C28 C 0.4150(4) 0.97639(17) 0.22754(16) 0.0300(5) Uani 1 1 d . . . . .
C29 C 0.2164(4) 0.9574(2) 0.25271(18) 0.0366(5) Uani 1 1 d . . . . .
H29 H 0.1559 0.9734 0.3030 0.044 Uiso 1 1 calc R U . . .
C30 C 0.1077(4) 0.9148(2) 0.20368(18) 0.0395(6) Uani 1 1 d . . . . .
H30 H -0.0269 0.9013 0.2206 0.047 Uiso 1 1 calc R U . . .
C31 C 0.1983(4) 0.89222(19) 0.12957(17) 0.0367(5) Uani 1 1 d . . . . .
C32 C 0.3975(4) 0.9090(2) 0.10459(18) 0.0377(5) Uani 1 1 d . . . . .
H32 H 0.4580 0.8920 0.0548 0.045 Uiso 1 1 calc R U . . .
C33 C 0.5060(4) 0.95126(19) 0.15406(18) 0.0349(5) Uani 1 1 d . . . . .
H33 H 0.6416 0.9630 0.1381 0.042 Uiso 1 1 calc R U . . .


#==============================================================================
_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
Br1 C31 1.899(2) . ?
S1 N4 1.604(2) . ?
S1 N3 1.612(2) . ?
N1 C15 1.389(3) . ?
N1 C1 1.397(3) . ?
N1 C28 1.432(3) . ?
N2 C15 1.311(3) . ?
N2 C14 1.387(3) . ?
N3 C17 1.343(3) . ?
N4 C18 1.350(3) . ?
C1 C14 1.369(4) . ?
C1 C2 1.431(3) . ?
C2 C3 1.406(4) . ?
C2 C7 1.429(3) . ?
C3 C4 1.373(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.395(5) . ?
C4 H4 0.9400 . ?
C5 C6 1.366(5) . ?
C5 H5 0.9400 . ?
C6 C7 1.414(4) . ?
C6 H6 0.9400 . ?
C7 C8 1.459(4) . ?
C8 C9 1.415(3) . ?
C8 C13 1.415(4) . ?
C9 C10 1.368(5) . ?
C9 H9 0.9400 . ?
C10 C11 1.385(5) . ?
C10 H10 0.9400 . ?
C11 C12 1.386(4) . ?
C11 H11 0.9400 . ?
C12 C13 1.406(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.438(3) . ?
C15 C16 1.476(3) . ?
C16 C21 1.365(3) . ?
C16 C17 1.415(3) . ?
C17 C18 1.440(3) . ?
C18 C19 1.438(3) . ?
C19 C20 1.377(3) . ?
C19 C22 1.490(3) . ?
C20 C21 1.423(3) . ?
C20 H20 0.9400 . ?
C21 H21 0.9400 . ?
C22 C23 1.375(4) . ?
C22 C27 1.397(4) . ?
C23 C24 1.386(4) . ?
C23 H23 0.9400 . ?
C24 C25 1.359(4) . ?
C24 H24 0.9400 . ?
C25 C26 1.372(5) . ?
C25 H25 0.9400 . ?
C26 C27 1.383(4) . ?
C26 H26 0.9400 . ?
C27 H27 0.9400 . ?
C28 C29 1.386(3) . ?
C28 C33 1.391(3) . ?
C29 C30 1.381(4) . ?
C29 H29 0.9400 . ?
C30 C31 1.380(4) . ?
C30 H30 0.9400 . ?
C31 C32 1.383(4) . ?
C32 C33 1.381(4) . ?
C32 H32 0.9400 . ?
C33 H33 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 101.05(11) . . ?
C15 N1 C1 105.59(19) . . ?
C15 N1 C28 124.99(18) . . ?
C1 N1 C28 125.75(19) . . ?
C15 N2 C14 104.5(2) . . ?
C17 N3 S1 106.26(16) . . ?
C18 N4 S1 107.14(16) . . ?
C14 C1 N1 105.4(2) . . ?
C14 C1 C2 123.6(2) . . ?
N1 C1 C2 131.0(2) . . ?
C3 C2 C7 119.8(2) . . ?
C3 C2 C1 124.3(2) . . ?
C7 C2 C1 115.9(2) . . ?
C4 C3 C2 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 122.2(3) . . ?
C5 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C6 C7 C2 116.7(3) . . ?
C6 C7 C8 122.4(2) . . ?
C2 C7 C8 120.9(2) . . ?
C9 C8 C13 116.8(3) . . ?
C9 C8 C7 122.6(3) . . ?
C13 C8 C7 120.6(2) . . ?
C10 C9 C8 121.6(3) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 120.9(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 119.6(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C8 121.1(2) . . ?
C12 C13 C14 121.6(2) . . ?
C8 C13 C14 117.3(2) . . ?
C1 C14 N2 111.6(2) . . ?
C1 C14 C13 121.5(2) . . ?
N2 C14 C13 126.8(2) . . ?
N2 C15 N1 112.9(2) . . ?
N2 C15 C16 125.5(2) . . ?
N1 C15 C16 121.5(2) . . ?
C21 C16 C17 116.8(2) . . ?
C21 C16 C15 123.7(2) . . ?
C17 C16 C15 119.5(2) . . ?
N3 C17 C16 124.7(2) . . ?
N3 C17 C18 113.6(2) . . ?
C16 C17 C18 121.8(2) . . ?
N4 C18 C19 127.5(2) . . ?
N4 C18 C17 112.0(2) . . ?
C19 C18 C17 120.5(2) . . ?
C20 C19 C18 114.9(2) . . ?
C20 C19 C22 121.5(2) . . ?
C18 C19 C22 123.6(2) . . ?
C19 C20 C21 124.4(2) . . ?
C19 C20 H20 117.8 . . ?
C21 C20 H20 117.8 . . ?
C16 C21 C20 121.6(2) . . ?
C16 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C23 C22 C27 116.4(2) . . ?
C23 C22 C19 122.9(2) . . ?
C27 C22 C19 120.7(2) . . ?
C22 C23 C24 122.3(3) . . ?
C22 C23 H23 118.8 . . ?
C24 C23 H23 118.8 . . ?
C25 C24 C23 120.3(3) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 119.1(3) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C25 C26 C27 120.6(3) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C26 C27 C22 121.3(3) . . ?
C26 C27 H27 119.4 . . ?
C22 C27 H27 119.4 . . ?
C29 C28 C33 120.2(2) . . ?
C29 C28 N1 121.4(2) . . ?
C33 C28 N1 118.3(2) . . ?
C30 C29 C28 119.8(2) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C31 C30 C29 119.4(2) . . ?
C31 C30 H30 120.3 . . ?
C29 C30 H30 120.3 . . ?
C30 C31 C32 121.5(2) . . ?
C30 C31 Br1 119.85(19) . . ?
C32 C31 Br1 118.61(18) . . ?
C33 C32 C31 118.9(2) . . ?
C33 C32 H32 120.6 . . ?
C31 C32 H32 120.6 . . ?
C32 C33 C28 120.1(2) . . ?
C32 C33 H33 119.9 . . ?
C28 C33 H33 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 S1 N3 C17 -0.6(2) . . . . ?
N3 S1 N4 C18 0.7(2) . . . . ?
C15 N1 C1 C14 0.0(2) . . . . ?
C28 N1 C1 C14 -159.2(2) . . . . ?
C15 N1 C1 C2 -177.4(2) . . . . ?
C28 N1 C1 C2 23.5(4) . . . . ?
C14 C1 C2 C3 -172.5(2) . . . . ?
N1 C1 C2 C3 4.4(4) . . . . ?
C14 C1 C2 C7 4.7(3) . . . . ?
N1 C1 C2 C7 -178.4(2) . . . . ?
C7 C2 C3 C4 2.6(4) . . . . ?
C1 C2 C3 C4 179.8(2) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C4 C5 C6 C7 1.0(5) . . . . ?
C5 C6 C7 C2 0.9(4) . . . . ?
C5 C6 C7 C8 -178.6(3) . . . . ?
C3 C2 C7 C6 -2.7(4) . . . . ?
C1 C2 C7 C6 179.9(2) . . . . ?
C3 C2 C7 C8 176.8(2) . . . . ?
C1 C2 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 C9 -3.2(4) . . . . ?
C2 C7 C8 C9 177.4(2) . . . . ?
C6 C7 C8 C13 177.1(3) . . . . ?
C2 C7 C8 C13 -2.4(4) . . . . ?
C13 C8 C9 C10 1.6(4) . . . . ?
C7 C8 C9 C10 -178.1(3) . . . . ?
C8 C9 C10 C11 -0.9(5) . . . . ?
C9 C10 C11 C12 -0.3(5) . . . . ?
C10 C11 C12 C13 0.8(4) . . . . ?
C11 C12 C13 C8 -0.1(4) . . . . ?
C11 C12 C13 C14 177.1(2) . . . . ?
C9 C8 C13 C12 -1.1(4) . . . . ?
C7 C8 C13 C12 178.7(2) . . . . ?
C9 C8 C13 C14 -178.4(2) . . . . ?
C7 C8 C13 C14 1.4(3) . . . . ?
N1 C1 C14 N2 0.0(3) . . . . ?
C2 C1 C14 N2 177.6(2) . . . . ?
N1 C1 C14 C13 176.5(2) . . . . ?
C2 C1 C14 C13 -6.0(4) . . . . ?
C15 N2 C14 C1 0.1(3) . . . . ?
C15 N2 C14 C13 -176.2(2) . . . . ?
C12 C13 C14 C1 -174.6(2) . . . . ?
C8 C13 C14 C1 2.7(3) . . . . ?
C12 C13 C14 N2 1.3(4) . . . . ?
C8 C13 C14 N2 178.6(2) . . . . ?
C14 N2 C15 N1 -0.1(3) . . . . ?
C14 N2 C15 C16 177.2(2) . . . . ?
C1 N1 C15 N2 0.1(3) . . . . ?
C28 N1 C15 N2 159.4(2) . . . . ?
C1 N1 C15 C16 -177.4(2) . . . . ?
C28 N1 C15 C16 -18.1(3) . . . . ?
N2 C15 C16 C21 113.0(3) . . . . ?
N1 C15 C16 C21 -69.8(3) . . . . ?
N2 C15 C16 C17 -67.5(3) . . . . ?
N1 C15 C16 C17 109.7(3) . . . . ?
S1 N3 C17 C16 -179.03(19) . . . . ?
S1 N3 C17 C18 0.2(3) . . . . ?
C21 C16 C17 N3 179.2(2) . . . . ?
C15 C16 C17 N3 -0.3(4) . . . . ?
C21 C16 C17 C18 0.0(3) . . . . ?
C15 C16 C17 C18 -179.5(2) . . . . ?
S1 N4 C18 C19 179.0(2) . . . . ?
S1 N4 C18 C17 -0.7(3) . . . . ?
N3 C17 C18 N4 0.3(3) . . . . ?
C16 C17 C18 N4 179.6(2) . . . . ?
N3 C17 C18 C19 -179.4(2) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
N4 C18 C19 C20 -179.1(2) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
N4 C18 C19 C22 -0.8(4) . . . . ?
C17 C18 C19 C22 178.8(2) . . . . ?
C18 C19 C20 C21 -0.8(4) . . . . ?
C22 C19 C20 C21 -179.2(2) . . . . ?
C17 C16 C21 C20 -0.3(4) . . . . ?
C15 C16 C21 C20 179.2(2) . . . . ?
C19 C20 C21 C16 0.7(4) . . . . ?
C20 C19 C22 C23 166.7(3) . . . . ?
C18 C19 C22 C23 -11.5(4) . . . . ?
C20 C19 C22 C27 -9.2(4) . . . . ?
C18 C19 C22 C27 172.6(3) . . . . ?
C27 C22 C23 C24 -1.7(5) . . . . ?
C19 C22 C23 C24 -177.7(3) . . . . ?
C22 C23 C24 C25 1.3(6) . . . . ?
C23 C24 C25 C26 0.4(6) . . . . ?
C24 C25 C26 C27 -1.6(6) . . . . ?
C25 C26 C27 C22 1.2(6) . . . . ?
C23 C22 C27 C26 0.5(5) . . . . ?
C19 C22 C27 C26 176.6(3) . . . . ?
C15 N1 C28 C29 80.8(3) . . . . ?
C1 N1 C28 C29 -123.9(3) . . . . ?
C15 N1 C28 C33 -99.3(3) . . . . ?
C1 N1 C28 C33 55.9(3) . . . . ?
C33 C28 C29 C30 -1.0(4) . . . . ?
N1 C28 C29 C30 178.9(2) . . . . ?
C28 C29 C30 C31 -0.4(4) . . . . ?
C29 C30 C31 C32 1.5(4) . . . . ?
C29 C30 C31 Br1 -177.77(19) . . . . ?
C30 C31 C32 C33 -1.2(4) . . . . ?
Br1 C31 C32 C33 178.05(19) . . . . ?
C31 C32 C33 C28 -0.1(4) . . . . ?
C29 C28 C33 C32 1.2(4) . . . . ?
N1 C28 C33 C32 -178.6(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
#==============================================================================
_chemical_name_systematic        
4-[1-(4-Bromophenyl)-1H-phenanthro[9,10-d]imidazol-2-yl]-7-phenylbenzo[c][1,2,5]thiadiazole
_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_sta345
_database_code_depnum_ccdc_archive 'CCDC 1995250'
loop_
_audit_author_name
_audit_author_address
'Suguru Ito'
;Yokohama National University
Japan
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-06-01 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C34 H22 N4 O S'
_chemical_formula_moiety         'C34 H22 N4 O S'
_chemical_formula_weight         534.63
_chemical_melting_point          479.75-482.55

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.72015(13)
_cell_length_b                   10.26595(12)
_cell_length_c                   14.23572(16)
_cell_angle_alpha                100.4892(9)
_cell_angle_beta                 96.5213(10)
_cell_angle_gamma                106.5436(11)
_cell_volume                     1318.19(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9260
_cell_measurement_theta_min      4.60
_cell_measurement_theta_max      74.91
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.064
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             556.00
_exptl_absorpt_coefficient_mu    1.371
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.66a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.714
_exptl_absorpt_correction_T_max  0.916

#==============================================================================
# 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 5.814
_diffrn_reflns_number            14064
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_theta_max         68.249
_diffrn_reflns_theta_min         4.612
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4822
_reflns_number_gt                4383
_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          0.0482
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1214
_refine_ls_wR_factor_gt          0.1181
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4822
_refine_ls_number_parameters     361
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0599P)²+0.4984P] 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         0.69
_refine_diff_density_min         -0.84
_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 0.08828(5) 1.07848(5) 0.78133(4) 0.05350(17) Uani 1 1 d . . . . .
O1 O 0.43957(16) 0.57363(13) 0.90243(10) 0.0513(4) Uani 1 1 d . . . . .
N1 N 0.59664(14) 1.06350(13) 0.76885(10) 0.0317(3) Uani 1 1 d . . . . .
N2 N 0.58345(15) 1.21101(14) 0.67238(10) 0.0347(3) Uani 1 1 d . . . . .
N3 N 0.25457(17) 1.09948(16) 0.76764(12) 0.0449(4) Uani 1 1 d . . . . .
N4 N 0.00103(16) 0.96410(15) 0.68358(12) 0.0428(4) Uani 1 1 d . . . . .
C1 C 0.72261(17) 1.17714(16) 0.79980(12) 0.0300(3) Uani 1 1 d . . . . .
C2 C 0.84570(17) 1.20895(16) 0.87623(12) 0.0307(3) Uani 1 1 d . . . . .
C3 C 0.85783(19) 1.12568(17) 0.94326(12) 0.0359(4) Uani 1 1 d . . . . .
H3 H 0.7808 1.0445 0.9407 0.043 Uiso 1 1 calc R U . . .
C4 C 0.9810(2) 1.16197(19) 1.01233(13) 0.0426(4) Uani 1 1 d . . . . .
H4 H 0.9874 1.1063 1.0573 0.051 Uiso 1 1 calc R U . . .
C5 C 1.0962(2) 1.2805(2) 1.01603(14) 0.0466(4) Uani 1 1 d . . . . .
H5 H 1.1816 1.3031 1.0621 0.056 Uiso 1 1 calc R U . . .
C6 C 1.0860(2) 1.36485(18) 0.95285(14) 0.0415(4) Uani 1 1 d . . . . .
H6 H 1.1646 1.4454 0.9570 0.050 Uiso 1 1 calc R U . . .
C7 C 0.96091(18) 1.33397(16) 0.88192(12) 0.0325(3) Uani 1 1 d . . . . .
C8 C 0.94889(17) 1.42785(16) 0.81739(12) 0.0331(4) Uani 1 1 d . . . . .
C9 C 1.0596(2) 1.55334(18) 0.82254(14) 0.0416(4) Uani 1 1 d . . . . .
H9 H 1.1481 1.5752 0.8654 0.050 Uiso 1 1 calc R U . . .
C10 C 1.0410(2) 1.64454(18) 0.76613(14) 0.0464(4) Uani 1 1 d . . . . .
H10 H 1.1163 1.7281 0.7715 0.056 Uiso 1 1 calc R U . . .
C11 C 0.9121(2) 1.61437(18) 0.70130(14) 0.0441(4) Uani 1 1 d . . . . .
H11 H 0.8990 1.6787 0.6646 0.053 Uiso 1 1 calc R U . . .
C12 C 0.8039(2) 1.49017(17) 0.69098(13) 0.0384(4) Uani 1 1 d . . . . .
H12 H 0.7179 1.4682 0.6456 0.046 Uiso 1 1 calc R U . . .
C13 C 0.82130(18) 1.39595(16) 0.74807(12) 0.0322(3) Uani 1 1 d . . . . .
C14 C 0.71084(17) 1.26522(16) 0.73929(12) 0.0312(3) Uani 1 1 d . . . . .
C15 C 0.51815(17) 1.09036(17) 0.69205(12) 0.0329(3) Uani 1 1 d . . . . .
C16 C 0.37161(17) 0.99847(16) 0.64230(12) 0.0333(4) Uani 1 1 d . . . . .
C17 C 0.24811(18) 1.01383(16) 0.68209(12) 0.0337(4) Uani 1 1 d . . . . .
C18 C 0.10292(17) 0.93597(16) 0.63328(12) 0.0323(3) Uani 1 1 d . . . . .
C19 C 0.07743(18) 0.83765(16) 0.54259(12) 0.0337(4) Uani 1 1 d . . . . .
C20 C 0.2008(2) 0.82700(19) 0.50741(13) 0.0415(4) Uani 1 1 d . . . . .
H20 H 0.1891 0.7642 0.4479 0.050 Uiso 1 1 calc R U . . .
C21 C 0.34418(19) 0.90512(19) 0.55556(13) 0.0410(4) Uani 1 1 d . . . . .
H21 H 0.4232 0.8923 0.5268 0.049 Uiso 1 1 calc R U . . .
C22 C -0.07090(19) 0.74803(18) 0.49348(12) 0.0363(4) Uani 1 1 d . . . . .
C23 C -0.1933(2) 0.7923(2) 0.50043(15) 0.0459(4) Uani 1 1 d . . . . .
H23 H -0.1815 0.8848 0.5314 0.055 Uiso 1 1 calc R U . . .
C24 C -0.3317(2) 0.7012(2) 0.46214(17) 0.0583(6) Uani 1 1 d . . . . .
H24 H -0.4132 0.7323 0.4674 0.070 Uiso 1 1 calc R U . . .
C25 C -0.3511(2) 0.5652(3) 0.41632(17) 0.0615(6) Uani 1 1 d . . . . .
H25 H -0.4456 0.5030 0.3923 0.074 Uiso 1 1 calc R U . . .
C26 C -0.2312(2) 0.5210(2) 0.40589(17) 0.0606(6) Uani 1 1 d . . . . .
H26 H -0.2439 0.4292 0.3729 0.073 Uiso 1 1 calc R U . . .
C27 C -0.0926(2) 0.6113(2) 0.44383(15) 0.0488(5) Uani 1 1 d . . . . .
H27 H -0.0116 0.5803 0.4361 0.059 Uiso 1 1 calc R U . . .
C28 C 0.55707(17) 0.93562(16) 0.80193(12) 0.0315(3) Uani 1 1 d . . . . .
C29 C 0.61187(19) 0.82989(17) 0.76649(13) 0.0369(4) Uani 1 1 d . . . . .
H29 H 0.6742 0.8415 0.7207 0.044 Uiso 1 1 calc R U . . .
C30 C 0.57506(19) 0.70603(17) 0.79849(13) 0.0382(4) Uani 1 1 d . . . . .
H30 H 0.6121 0.6339 0.7743 0.046 Uiso 1 1 calc R U . . .
C31 C 0.48333(19) 0.68987(17) 0.86631(13) 0.0366(4) Uani 1 1 d . . . . .
C32 C 0.42991(19) 0.79766(18) 0.90242(13) 0.0401(4) Uani 1 1 d . . . . .
H32 H 0.3688 0.7871 0.9490 0.048 Uiso 1 1 calc R U . . .
C33 C 0.46614(18) 0.91988(17) 0.87017(13) 0.0367(4) Uani 1 1 d . . . . .
H33 H 0.4293 0.9922 0.8944 0.044 Uiso 1 1 calc R U . . .
C34 C 0.4788(3) 0.4542(2) 0.86116(17) 0.0612(6) Uani 1 1 d . . . . .
H34A H 0.4410 0.3794 0.8934 0.073 Uiso 1 1 calc R U . . .
H34B H 0.4378 0.4239 0.7925 0.073 Uiso 1 1 calc R U . . .
H34C H 0.5841 0.4784 0.8696 0.073 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.66a (Rigaku OD, 2019)'
_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 1.6080(16) . ?
S1 N4 1.6138(17) . ?
O1 C31 1.361(2) . ?
O1 C34 1.431(3) . ?
N1 C15 1.376(2) . ?
N1 C1 1.390(2) . ?
N1 C28 1.4393(19) . ?
N2 C15 1.317(2) . ?
N2 C14 1.377(2) . ?
N3 C17 1.350(2) . ?
N4 C18 1.351(2) . ?
C1 C14 1.376(2) . ?
C1 C2 1.440(2) . ?
C2 C3 1.409(2) . ?
C2 C7 1.425(2) . ?
C3 C4 1.373(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.371(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.409(2) . ?
C6 H6 0.9400 . ?
C7 C8 1.466(2) . ?
C8 C9 1.408(2) . ?
C8 C13 1.411(2) . ?
C9 C10 1.375(3) . ?
C9 H9 0.9400 . ?
C10 C11 1.390(3) . ?
C10 H10 0.9400 . ?
C11 C12 1.374(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.405(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.434(2) . ?
C15 C16 1.477(2) . ?
C16 C21 1.365(2) . ?
C16 C17 1.420(2) . ?
C17 C18 1.430(2) . ?
C18 C19 1.434(2) . ?
C19 C20 1.375(2) . ?
C19 C22 1.482(2) . ?
C20 C21 1.415(3) . ?
C20 H20 0.9400 . ?
C21 H21 0.9400 . ?
C22 C23 1.396(3) . ?
C22 C27 1.396(3) . ?
C23 C24 1.383(3) . ?
C23 H23 0.9400 . ?
C24 C25 1.378(3) . ?
C24 H24 0.9400 . ?
C25 C26 1.379(3) . ?
C25 H25 0.9400 . ?
C26 C27 1.381(3) . ?
C26 H26 0.9400 . ?
C27 H27 0.9400 . ?
C28 C29 1.381(2) . ?
C28 C33 1.386(2) . ?
C29 C30 1.393(2) . ?
C29 H29 0.9400 . ?
C30 C31 1.387(3) . ?
C30 H30 0.9400 . ?
C31 C32 1.393(2) . ?
C32 C33 1.380(2) . ?
C32 H32 0.9400 . ?
C33 H33 0.9400 . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C34 H34C 0.9700 . ?

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 101.35(8) . . ?
C31 O1 C34 118.05(16) . . ?
C15 N1 C1 106.29(13) . . ?
C15 N1 C28 124.80(13) . . ?
C1 N1 C28 128.69(13) . . ?
C15 N2 C14 104.54(13) . . ?
C17 N3 S1 105.87(12) . . ?
C18 N4 S1 106.48(12) . . ?
C14 C1 N1 104.97(14) . . ?
C14 C1 C2 122.78(14) . . ?
N1 C1 C2 132.24(14) . . ?
C3 C2 C7 119.58(15) . . ?
C3 C2 C1 124.49(15) . . ?
C7 C2 C1 115.93(14) . . ?
C4 C3 C2 120.63(16) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.21(17) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.30(17) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 121.75(17) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C6 C7 C2 117.43(15) . . ?
C6 C7 C8 121.26(15) . . ?
C2 C7 C8 121.30(15) . . ?
C9 C8 C13 117.17(16) . . ?
C9 C8 C7 122.60(16) . . ?
C13 C8 C7 120.22(14) . . ?
C10 C9 C8 121.36(18) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 120.67(17) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 119.76(17) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.18(18) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.73(15) . . ?
C12 C13 C14 121.80(16) . . ?
C8 C13 C14 117.47(15) . . ?
C1 C14 N2 111.54(14) . . ?
C1 C14 C13 122.04(15) . . ?
N2 C14 C13 126.42(15) . . ?
N2 C15 N1 112.65(14) . . ?
N2 C15 C16 123.85(15) . . ?
N1 C15 C16 123.34(14) . . ?
C21 C16 C17 116.45(15) . . ?
C21 C16 C15 124.46(15) . . ?
C17 C16 C15 118.90(15) . . ?
N3 C17 C16 124.57(16) . . ?
N3 C17 C18 113.88(15) . . ?
C16 C17 C18 121.55(15) . . ?
N4 C18 C17 112.42(15) . . ?
N4 C18 C19 126.79(15) . . ?
C17 C18 C19 120.77(15) . . ?
C20 C19 C18 115.23(15) . . ?
C20 C19 C22 122.45(16) . . ?
C18 C19 C22 122.23(15) . . ?
C19 C20 C21 123.80(16) . . ?
C19 C20 H20 118.1 . . ?
C21 C20 H20 118.1 . . ?
C16 C21 C20 122.20(16) . . ?
C16 C21 H21 118.9 . . ?
C20 C21 H21 118.9 . . ?
C23 C22 C27 117.98(17) . . ?
C23 C22 C19 122.08(16) . . ?
C27 C22 C19 119.80(16) . . ?
C24 C23 C22 120.57(19) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C25 C24 C23 120.6(2) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 119.6(2) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C25 C26 C27 120.2(2) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C22 121.01(19) . . ?
C26 C27 H27 119.5 . . ?
C22 C27 H27 119.5 . . ?
C29 C28 C33 120.31(15) . . ?
C29 C28 N1 119.70(14) . . ?
C33 C28 N1 119.98(14) . . ?
C28 C29 C30 120.18(16) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C31 C30 C29 119.53(16) . . ?
C31 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
O1 C31 C30 124.69(16) . . ?
O1 C31 C32 115.44(16) . . ?
C30 C31 C32 119.87(15) . . ?
C33 C32 C31 120.37(16) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C32 C33 C28 119.72(15) . . ?
C32 C33 H33 120.1 . . ?
C28 C33 H33 120.1 . . ?
O1 C34 H34A 109.5 . . ?
O1 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O1 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 S1 N3 C17 -0.02(14) . . . . ?
N3 S1 N4 C18 -0.12(14) . . . . ?
C15 N1 C1 C14 0.19(16) . . . . ?
C28 N1 C1 C14 175.01(15) . . . . ?
C15 N1 C1 C2 -179.78(16) . . . . ?
C28 N1 C1 C2 -5.0(3) . . . . ?
C14 C1 C2 C3 176.03(15) . . . . ?
N1 C1 C2 C3 -4.0(3) . . . . ?
C14 C1 C2 C7 -4.1(2) . . . . ?
N1 C1 C2 C7 175.90(15) . . . . ?
C7 C2 C3 C4 -1.7(2) . . . . ?
C1 C2 C3 C4 178.23(15) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 2.2(3) . . . . ?
C4 C5 C6 C7 -0.8(3) . . . . ?
C5 C6 C7 C2 -1.7(3) . . . . ?
C5 C6 C7 C8 177.48(16) . . . . ?
C3 C2 C7 C6 2.9(2) . . . . ?
C1 C2 C7 C6 -177.02(14) . . . . ?
C3 C2 C7 C8 -176.26(14) . . . . ?
C1 C2 C7 C8 3.8(2) . . . . ?
C6 C7 C8 C9 -0.4(2) . . . . ?
C2 C7 C8 C9 178.74(15) . . . . ?
C6 C7 C8 C13 -178.82(15) . . . . ?
C2 C7 C8 C13 0.3(2) . . . . ?
C13 C8 C9 C10 3.5(3) . . . . ?
C7 C8 C9 C10 -175.03(16) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 C12 -2.2(3) . . . . ?
C10 C11 C12 C13 2.2(3) . . . . ?
C11 C12 C13 C8 0.7(3) . . . . ?
C11 C12 C13 C14 -179.92(16) . . . . ?
C9 C8 C13 C12 -3.5(2) . . . . ?
C7 C8 C13 C12 175.07(14) . . . . ?
C9 C8 C13 C14 177.16(14) . . . . ?
C7 C8 C13 C14 -4.3(2) . . . . ?
N1 C1 C14 N2 -0.07(17) . . . . ?
C2 C1 C14 N2 179.90(14) . . . . ?
N1 C1 C14 C13 -179.91(14) . . . . ?
C2 C1 C14 C13 0.1(2) . . . . ?
C15 N2 C14 C1 -0.08(18) . . . . ?
C15 N2 C14 C13 179.75(15) . . . . ?
C12 C13 C14 C1 -175.15(15) . . . . ?
C8 C13 C14 C1 4.2(2) . . . . ?
C12 C13 C14 N2 5.0(3) . . . . ?
C8 C13 C14 N2 -175.60(15) . . . . ?
C14 N2 C15 N1 0.21(18) . . . . ?
C14 N2 C15 C16 175.83(15) . . . . ?
C1 N1 C15 N2 -0.26(18) . . . . ?
C28 N1 C15 N2 -175.34(14) . . . . ?
C1 N1 C15 C16 -175.90(14) . . . . ?
C28 N1 C15 C16 9.0(2) . . . . ?
N2 C15 C16 C21 83.8(2) . . . . ?
N1 C15 C16 C21 -101.1(2) . . . . ?
N2 C15 C16 C17 -91.1(2) . . . . ?
N1 C15 C16 C17 84.1(2) . . . . ?
S1 N3 C17 C16 -179.22(14) . . . . ?
S1 N3 C17 C18 0.15(18) . . . . ?
C21 C16 C17 N3 178.95(17) . . . . ?
C15 C16 C17 N3 -5.8(2) . . . . ?
C21 C16 C17 C18 -0.4(2) . . . . ?
C15 C16 C17 C18 174.89(14) . . . . ?
S1 N4 C18 C17 0.21(17) . . . . ?
S1 N4 C18 C19 178.28(14) . . . . ?
N3 C17 C18 N4 -0.2(2) . . . . ?
C16 C17 C18 N4 179.15(15) . . . . ?
N3 C17 C18 C19 -178.44(15) . . . . ?
C16 C17 C18 C19 0.9(2) . . . . ?
N4 C18 C19 C20 -178.83(17) . . . . ?
C17 C18 C19 C20 -0.9(2) . . . . ?
N4 C18 C19 C22 -2.4(3) . . . . ?
C17 C18 C19 C22 175.57(15) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
C22 C19 C20 C21 -176.09(17) . . . . ?
C17 C16 C21 C20 -0.2(3) . . . . ?
C15 C16 C21 C20 -175.15(16) . . . . ?
C19 C20 C21 C16 0.2(3) . . . . ?
C20 C19 C22 C23 -151.64(18) . . . . ?
C18 C19 C22 C23 32.1(2) . . . . ?
C20 C19 C22 C27 32.8(3) . . . . ?
C18 C19 C22 C27 -143.39(17) . . . . ?
C27 C22 C23 C24 2.3(3) . . . . ?
C19 C22 C23 C24 -173.31(18) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C26 -2.1(4) . . . . ?
C24 C25 C26 C27 2.0(4) . . . . ?
C25 C26 C27 C22 0.2(3) . . . . ?
C23 C22 C27 C26 -2.4(3) . . . . ?
C19 C22 C27 C26 173.33(19) . . . . ?
C15 N1 C28 C29 92.7(2) . . . . ?
C1 N1 C28 C29 -81.3(2) . . . . ?
C15 N1 C28 C33 -88.3(2) . . . . ?
C1 N1 C28 C33 97.7(2) . . . . ?
C33 C28 C29 C30 0.6(3) . . . . ?
N1 C28 C29 C30 179.57(15) . . . . ?
C28 C29 C30 C31 -0.1(3) . . . . ?
C34 O1 C31 C30 -6.4(3) . . . . ?
C34 O1 C31 C32 173.86(18) . . . . ?
C29 C30 C31 O1 179.72(16) . . . . ?
C29 C30 C31 C32 -0.6(3) . . . . ?
O1 C31 C32 C33 -179.39(16) . . . . ?
C30 C31 C32 C33 0.9(3) . . . . ?
C31 C32 C33 C28 -0.5(3) . . . . ?
C29 C28 C33 C32 -0.3(3) . . . . ?
N1 C28 C33 C32 -179.27(15) . . . . ?

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

#==============================================================================
# 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
#==============================================================================
_chemical_name_systematic        
4-[1-(4-Methoxyphenyl)-1H-phenanthro[9,10-d]imidazol-2-yl]-7-phenylbenzo[c][1,2,5]thiadiazole
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform/hexane'
_exptl_crystal_preparation       Luminescent
