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

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

data_mina204_3
_database_code_depnum_ccdc_archive 'CCDC 1947301'
loop_
_audit_author_name
_audit_author_address
'Suguru Ito'
;Yokohama National University
Japan
;
_audit_update_record             
;
2019-08-15 deposited with the CCDC.	2019-09-12 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C21 H14 S'
_chemical_formula_moiety         'C21 H14 S'
_chemical_formula_weight         298.40
_chemical_melting_point          361.15-363.15
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# 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           1
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
#------------------------------------------------------------------------------
_cell_length_a                   7.6239(3)
_cell_length_b                   7.7590(2)
_cell_length_c                   25.3429(9)
_cell_angle_alpha                93.231(3)
_cell_angle_beta                 93.462(3)
_cell_angle_gamma                91.842(3)
_cell_volume                     1493.06(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6745
_cell_measurement_theta_min      5.28
_cell_measurement_theta_max      74.62
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.571
_exptl_crystal_size_mid          0.522
_exptl_crystal_size_min          0.284
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624.00
_exptl_absorpt_coefficient_mu    1.839
_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  0.277
_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            15874
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_theta_max         68.243
_diffrn_reflns_theta_min         5.255
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.642
_diffrn_reflns_point_group_measured_fraction_full 0.643
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       30
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             7028
_reflns_number_gt                6367
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.290
_reflns_Friedel_fraction_max     0.288
_reflns_Friedel_fraction_full    0.290

#==============================================================================
# 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          0.1257
_refine_ls_R_factor_gt           0.1215
_refine_ls_wR_factor_ref         0.3754
_refine_ls_wR_factor_gt          0.3706
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         7028
_refine_ls_number_parameters     793
_refine_ls_goodness_of_fit_ref   1.719
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)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         0.87
_refine_diff_density_min         -0.51
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1193 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(3)

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)
;
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 0.8767(4) 0.4076(5) -0.15402(13) 0.0682(9) Uani 1 1 d . . . . .
S2 S 0.1928(5) 0.8777(5) -0.14225(13) 0.0676(9) Uani 1 1 d . . . . .
S3 S 0.5028(7) 0.4329(6) 0.73561(14) 0.0882(13) Uani 1 1 d . . . . .
S4 S 1.0304(8) 1.1184(6) 0.73276(15) 0.0934(15) Uani 1 1 d . . . . .
C1 C 0.7706(15) 0.5556(19) -0.1170(5) 0.059(3) Uani 1 1 d . . . . .
C2 C 0.7733(14) 0.5123(19) -0.0651(4) 0.055(3) Uani 1 1 d . . . . .
H2 H 0.7276 0.5831 -0.0382 0.066 Uiso 1 1 calc R U . . .
C3 C 0.8526(14) 0.3481(19) -0.0550(5) 0.057(3) Uani 1 1 d . . . . .
C4 C 0.917(2) 0.285(2) -0.1023(5) 0.069(4) Uani 1 1 d . . . . .
H4 H 0.9784 0.1825 -0.1052 0.083 Uiso 1 1 calc R U . . .
C5 C 0.8588(13) 0.2639(17) -0.0054(5) 0.052(3) Uani 1 1 d . . . . .
C6 C 0.8154(17) 0.0826(18) -0.0062(6) 0.062(3) Uani 1 1 d . . . . .
H6 H 0.8014 0.0200 -0.0391 0.074 Uiso 1 1 calc R U . . .
C7 C 0.7937(15) -0.0027(15) 0.0380(5) 0.054(3) Uani 1 1 d . . . . .
H7 H 0.7584 -0.1202 0.0350 0.064 Uiso 1 1 calc R U . . .
C8 C 0.8235(13) 0.0829(15) 0.0892(5) 0.049(2) Uani 1 1 d . . . . .
C9 C 0.8048(14) 0.0016(16) 0.1357(5) 0.055(3) Uani 1 1 d . . . . .
H9 H 0.7653 -0.1147 0.1339 0.066 Uiso 1 1 calc R U . . .
C10 C 0.8414(16) 0.0837(14) 0.1837(5) 0.054(3) Uani 1 1 d . . . . .
H10 H 0.8297 0.0215 0.2142 0.065 Uiso 1 1 calc R U . . .
C11 C 0.8976(14) 0.2623(17) 0.1900(5) 0.053(3) Uani 1 1 d . . . . .
C12 C 0.9352(17) 0.3564(17) 0.2383(5) 0.058(3) Uani 1 1 d . . . . .
H12 H 0.9216 0.3007 0.2698 0.070 Uiso 1 1 calc R U . . .
C13 C 0.9892(18) 0.5204(18) 0.2414(5) 0.061(3) Uani 1 1 d . . . . .
H13 H 1.0151 0.5768 0.2749 0.073 Uiso 1 1 calc R U . . .
C14 C 1.0088(14) 0.6125(15) 0.1959(5) 0.050(2) Uani 1 1 d . . . . .
H14 H 1.0447 0.7299 0.1986 0.060 Uiso 1 1 calc R U . . .
C15 C 0.9734(12) 0.5251(14) 0.1463(4) 0.044(2) Uani 1 1 d . . . . .
C16 C 0.9931(12) 0.6096(14) 0.0987(4) 0.045(2) Uani 1 1 d . . . . .
H16 H 1.0326 0.7260 0.1008 0.054 Uiso 1 1 calc R U . . .
C17 C 0.9569(12) 0.5284(14) 0.0506(4) 0.045(2) Uani 1 1 d . . . . .
H17 H 0.9697 0.5899 0.0201 0.054 Uiso 1 1 calc R U . . .
C18 C 0.8985(13) 0.3474(15) 0.0451(4) 0.046(2) Uani 1 1 d . . . . .
C19 C 0.8788(11) 0.2609(13) 0.0916(4) 0.041(2) Uani 1 1 d . . . . .
C20 C 0.9170(12) 0.3507(13) 0.1423(4) 0.041(2) Uani 1 1 d . . . . .
C21 C 0.6900(19) 0.710(2) -0.1389(6) 0.067(3) Uani 1 1 d . . . . .
H21A H 0.7064 0.7104 -0.1766 0.081 Uiso 1 1 calc R U . . .
H21B H 0.5654 0.7080 -0.1332 0.081 Uiso 1 1 calc R U . . .
H21C H 0.7458 0.8140 -0.1213 0.081 Uiso 1 1 calc R U . . .
C22 C 0.3257(18) 1.0341(18) -0.1101(5) 0.060(3) Uani 1 1 d . . . . .
C23 C 0.3768(15) 0.9862(18) -0.0601(4) 0.055(3) Uani 1 1 d . . . . .
H23 H 0.4556 1.0541 -0.0370 0.066 Uiso 1 1 calc R U . . .
C24 C 0.3028(15) 0.8292(16) -0.0464(4) 0.050(2) Uani 1 1 d . . . . .
C25 C 0.1940(18) 0.753(2) -0.0876(5) 0.064(3) Uani 1 1 d . . . . .
H25 H 0.1295 0.6487 -0.0860 0.077 Uiso 1 1 calc R U . . .
C26 C 0.3413(15) 0.7408(17) 0.0029(5) 0.055(3) Uani 1 1 d . . . . .
C27 C 0.3881(15) 0.5691(16) -0.0014(5) 0.051(2) Uani 1 1 d . . . . .
H27 H 0.3841 0.5108 -0.0350 0.061 Uiso 1 1 calc R U . . .
C28 C 0.4414(17) 0.4811(17) 0.0435(5) 0.058(3) Uani 1 1 d . . . . .
H28 H 0.4702 0.3644 0.0396 0.070 Uiso 1 1 calc R U . . .
C29 C 0.4518(12) 0.5649(14) 0.0935(4) 0.043(2) Uani 1 1 d . . . . .
C30 C 0.5064(14) 0.4831(18) 0.1405(5) 0.055(3) Uani 1 1 d . . . . .
H30 H 0.5411 0.3680 0.1371 0.066 Uiso 1 1 calc R U . . .
C31 C 0.5109(15) 0.5589(16) 0.1879(5) 0.052(2) Uani 1 1 d . . . . .
H31 H 0.5494 0.4990 0.2174 0.062 Uiso 1 1 calc R U . . .
C32 C 0.4569(14) 0.7345(15) 0.1949(4) 0.046(2) Uani 1 1 d . . . . .
C33 C 0.4556(18) 0.8193(15) 0.2443(5) 0.056(3) Uani 1 1 d . . . . .
H33 H 0.4910 0.7601 0.2743 0.067 Uiso 1 1 calc R U . . .
C34 C 0.4039(19) 0.9895(18) 0.2515(5) 0.062(3) Uani 1 1 d . . . . .
H34 H 0.4090 1.0454 0.2854 0.074 Uiso 1 1 calc R U . . .
C35 C 0.3450(14) 1.0742(17) 0.2077(4) 0.053(3) Uani 1 1 d . . . . .
H35 H 0.3055 1.1871 0.2128 0.064 Uiso 1 1 calc R U . . .
C36 C 0.3417(13) 0.9993(15) 0.1563(5) 0.049(2) Uani 1 1 d . . . . .
C37 C 0.2868(14) 1.0762(14) 0.1102(4) 0.048(2) Uani 1 1 d . . . . .
H37 H 0.2452 1.1888 0.1135 0.058 Uiso 1 1 calc R U . . .
C38 C 0.2891(13) 1.0008(14) 0.0615(5) 0.046(2) Uani 1 1 d . . . . .
H38 H 0.2518 1.0621 0.0321 0.055 Uiso 1 1 calc R U . . .
C39 C 0.3470(14) 0.8297(16) 0.0533(4) 0.049(2) Uani 1 1 d . . . . .
C40 C 0.4007(14) 0.7388(15) 0.0987(5) 0.047(2) Uani 1 1 d . . . . .
C41 C 0.4022(12) 0.8272(14) 0.1494(4) 0.041(2) Uani 1 1 d . . . . .
C42 C 0.388(2) 1.189(2) -0.1377(6) 0.079(4) Uani 1 1 d . . . . .
H42A H 0.3285 1.1891 -0.1727 0.095 Uiso 1 1 calc R U . . .
H42B H 0.3615 1.2938 -0.1173 0.095 Uiso 1 1 calc R U . . .
H42C H 0.5138 1.1853 -0.1410 0.095 Uiso 1 1 calc R U . . .
C43 C 0.346(2) 0.5373(16) 0.7005(5) 0.065(3) Uani 1 1 d . . . . .
C44 C 0.390(2) 0.5470(14) 0.6501(5) 0.058(3) Uani 1 1 d . . . . .
H44 H 0.3168 0.5975 0.6245 0.069 Uiso 1 1 calc R U . . .
C45 C 0.555(2) 0.4748(14) 0.6381(5) 0.063(3) Uani 1 1 d . . . . .
C46 C 0.629(2) 0.400(2) 0.6819(6) 0.080(4) Uani 1 1 d . . . . .
H46 H 0.7333 0.3386 0.6823 0.096 Uiso 1 1 calc R U . . .
C47 C 0.6440(16) 0.4799(13) 0.5875(5) 0.052(3) Uani 1 1 d . . . . .
C48 C 0.8230(18) 0.5336(13) 0.5882(5) 0.057(3) Uani 1 1 d . . . . .
H48 H 0.8858 0.5570 0.6210 0.068 Uiso 1 1 calc R U . . .
C49 C 0.9083(16) 0.5527(15) 0.5426(6) 0.059(3) Uani 1 1 d . . . . .
H49 H 1.0294 0.5811 0.5446 0.070 Uiso 1 1 calc R U . . .
C50 C 0.8150(15) 0.5298(12) 0.4932(5) 0.048(2) Uani 1 1 d . . . . .
C51 C 0.899(2) 0.5557(17) 0.4450(6) 0.067(4) Uani 1 1 d . . . . .
H51 H 1.0178 0.5931 0.4463 0.081 Uiso 1 1 calc R U . . .
C52 C 0.8111(16) 0.5273(17) 0.3994(6) 0.059(3) Uani 1 1 d . . . . .
H52 H 0.8705 0.5461 0.3687 0.070 Uiso 1 1 calc R U . . .
C53 C 0.6314(16) 0.4700(15) 0.3929(5) 0.052(3) Uani 1 1 d . . . . .
C54 C 0.536(2) 0.4424(18) 0.3430(5) 0.062(3) Uani 1 1 d . . . . .
H54 H 0.5900 0.4677 0.3117 0.075 Uiso 1 1 calc R U . . .
C55 C 0.365(2) 0.3778(18) 0.3407(5) 0.070(4) Uani 1 1 d . . . . .
H55 H 0.3043 0.3524 0.3076 0.084 Uiso 1 1 calc R U . . .
C56 C 0.2795(18) 0.3498(16) 0.3869(5) 0.058(3) Uani 1 1 d . . . . .
H56 H 0.1612 0.3105 0.3844 0.070 Uiso 1 1 calc R U . . .
C57 C 0.3649(17) 0.3785(13) 0.4354(5) 0.048(2) Uani 1 1 d . . . . .
C58 C 0.2847(15) 0.3522(13) 0.4849(4) 0.047(2) Uani 1 1 d . . . . .
H58 H 0.1670 0.3116 0.4837 0.057 Uiso 1 1 calc R U . . .
C59 C 0.3698(16) 0.3827(13) 0.5318(4) 0.047(2) Uani 1 1 d . . . . .
H59 H 0.3100 0.3618 0.5623 0.056 Uiso 1 1 calc R U . . .
C60 C 0.5503(14) 0.4468(12) 0.5382(4) 0.043(2) Uani 1 1 d . . . . .
C61 C 0.6360(15) 0.4728(13) 0.4913(4) 0.045(2) Uani 1 1 d . . . . .
C62 C 0.5417(13) 0.4404(12) 0.4401(4) 0.042(2) Uani 1 1 d . . . . .
C63 C 0.189(3) 0.616(3) 0.7259(6) 0.098(6) Uani 1 1 d . . . . .
H63A H 0.1901 0.5880 0.7628 0.117 Uiso 1 1 calc R U . . .
H63B H 0.1951 0.7403 0.7237 0.117 Uiso 1 1 calc R U . . .
H63C H 0.0809 0.5693 0.7074 0.117 Uiso 1 1 calc R U . . .
C64 C 0.850(4) 0.994(2) 0.7013(6) 0.111(8) Uani 1 1 d . . . . .
C65 C 0.893(2) 0.9583(18) 0.6509(5) 0.068(4) Uani 1 1 d . . . . .
H65 H 0.8152 0.8920 0.6269 0.082 Uiso 1 1 calc R U . . .
C66 C 1.056(2) 1.0225(16) 0.6351(5) 0.068(4) Uani 1 1 d . . . . .
C67 C 1.137(3) 1.113(2) 0.6774(6) 0.084(5) Uani 1 1 d . . . . .
H67 H 1.2470 1.1697 0.6756 0.100 Uiso 1 1 calc R U . . .
C68 C 1.1347(17) 0.9862(14) 0.5845(5) 0.053(3) Uani 1 1 d . . . . .
C69 C 1.3085(19) 0.9323(16) 0.5842(6) 0.062(3) Uani 1 1 d . . . . .
H69 H 1.3737 0.9240 0.6166 0.074 Uiso 1 1 calc R U . . .
C70 C 1.386(2) 0.8911(15) 0.5377(6) 0.064(3) Uani 1 1 d . . . . .
H70 H 1.5046 0.8617 0.5388 0.077 Uiso 1 1 calc R U . . .
C71 C 1.2912(15) 0.8921(13) 0.4888(5) 0.049(2) Uani 1 1 d . . . . .
C72 C 1.364(2) 0.8478(17) 0.4400(7) 0.070(4) Uani 1 1 d . . . . .
H72 H 1.4802 0.8113 0.4410 0.084 Uiso 1 1 calc R U . . .
C73 C 1.2790(19) 0.8543(15) 0.3933(5) 0.059(3) Uani 1 1 d . . . . .
H73 H 1.3333 0.8184 0.3624 0.070 Uiso 1 1 calc R U . . .
C74 C 1.1004(16) 0.9175(14) 0.3897(5) 0.052(3) Uani 1 1 d . . . . .
C75 C 1.006(2) 0.9330(17) 0.3414(5) 0.070(4) Uani 1 1 d . . . . .
H75 H 1.0583 0.9050 0.3095 0.084 Uiso 1 1 calc R U . . .
C76 C 0.831(2) 0.9913(18) 0.3406(5) 0.069(4) Uani 1 1 d . . . . .
H76 H 0.7659 0.9988 0.3082 0.082 Uiso 1 1 calc R U . . .
C77 C 0.7580(17) 1.0357(16) 0.3866(5) 0.055(3) Uani 1 1 d . . . . .
H77 H 0.6426 1.0753 0.3851 0.066 Uiso 1 1 calc R U . . .
C78 C 0.8446(17) 1.0258(12) 0.4355(4) 0.049(2) Uani 1 1 d . . . . .
C79 C 0.7739(15) 1.0741(14) 0.4839(4) 0.049(2) Uani 1 1 d . . . . .
H79 H 0.6607 1.1188 0.4834 0.058 Uiso 1 1 calc R U . . .
C80 C 0.8623(17) 1.0586(14) 0.5309(4) 0.051(3) Uani 1 1 d . . . . .
H80 H 0.8069 1.0890 0.5620 0.061 Uiso 1 1 calc R U . . .
C81 C 1.0359(16) 0.9980(13) 0.5351(4) 0.047(2) Uani 1 1 d . . . . .
C82 C 1.1192(18) 0.9494(13) 0.4871(5) 0.053(3) Uani 1 1 d . . . . .
C83 C 1.0265(15) 0.9648(12) 0.4378(4) 0.044(2) Uani 1 1 d . . . . .
C84 C 0.705(3) 0.956(2) 0.7301(6) 0.102(7) Uani 1 1 d . . . . .
H84A H 0.7253 1.0064 0.7660 0.122 Uiso 1 1 calc R U . . .
H84B H 0.6012 1.0041 0.7135 0.122 Uiso 1 1 calc R U . . .
H84C H 0.6887 0.8320 0.7309 0.122 Uiso 1 1 calc R U . . .


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

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

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.679(16) . ?
S1 C1 1.698(14) . ?
S2 C22 1.695(14) . ?
S2 C25 1.732(15) . ?
S3 C43 1.703(16) . ?
S3 C46 1.73(2) . ?
S4 C67 1.66(2) . ?
S4 C64 1.77(2) . ?
C1 C2 1.376(16) . ?
C1 C21 1.49(2) . ?
C2 C3 1.46(2) . ?
C2 H2 0.9400 . ?
C3 C4 1.392(16) . ?
C3 C5 1.447(18) . ?
C4 H4 0.9400 . ?
C5 C18 1.414(16) . ?
C5 C6 1.434(19) . ?
C6 C7 1.349(19) . ?
C6 H6 0.9400 . ?
C7 C8 1.425(17) . ?
C7 H7 0.9400 . ?
C8 C9 1.381(17) . ?
C8 C19 1.428(15) . ?
C9 C10 1.351(18) . ?
C9 H9 0.9400 . ?
C10 C11 1.435(17) . ?
C10 H10 0.9400 . ?
C11 C12 1.397(17) . ?
C11 C20 1.436(16) . ?
C12 C13 1.321(19) . ?
C12 H12 0.9400 . ?
C13 C14 1.403(17) . ?
C13 H13 0.9400 . ?
C14 C15 1.402(15) . ?
C14 H14 0.9400 . ?
C15 C20 1.403(15) . ?
C15 C16 1.418(15) . ?
C16 C17 1.349(15) . ?
C16 H16 0.9400 . ?
C17 C18 1.456(16) . ?
C17 H17 0.9400 . ?
C18 C19 1.401(15) . ?
C19 C20 1.436(14) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C22 C23 1.376(17) . ?
C22 C42 1.51(2) . ?
C23 C24 1.397(17) . ?
C23 H23 0.9400 . ?
C24 C25 1.385(16) . ?
C24 C26 1.478(16) . ?
C25 H25 0.9400 . ?
C26 C27 1.390(18) . ?
C26 C39 1.414(15) . ?
C27 C28 1.405(18) . ?
C27 H27 0.9400 . ?
C28 C29 1.387(16) . ?
C28 H28 0.9400 . ?
C29 C40 1.418(15) . ?
C29 C30 1.427(15) . ?
C30 C31 1.306(17) . ?
C30 H30 0.9400 . ?
C31 C32 1.440(16) . ?
C31 H31 0.9400 . ?
C32 C33 1.383(15) . ?
C32 C41 1.441(14) . ?
C33 C34 1.395(19) . ?
C33 H33 0.9400 . ?
C34 C35 1.380(18) . ?
C34 H34 0.9400 . ?
C35 C36 1.395(15) . ?
C35 H35 0.9400 . ?
C36 C37 1.390(16) . ?
C36 C41 1.432(16) . ?
C37 C38 1.338(15) . ?
C37 H37 0.9400 . ?
C38 C39 1.420(16) . ?
C38 H38 0.9400 . ?
C39 C40 1.427(16) . ?
C40 C41 1.422(15) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C42 H42C 0.9700 . ?
C43 C44 1.343(17) . ?
C43 C63 1.52(3) . ?
C44 C45 1.44(2) . ?
C44 H44 0.9400 . ?
C45 C46 1.379(17) . ?
C45 C47 1.490(18) . ?
C46 H46 0.9400 . ?
C47 C60 1.407(16) . ?
C47 C48 1.413(19) . ?
C48 C49 1.371(19) . ?
C48 H48 0.9400 . ?
C49 C50 1.403(18) . ?
C49 H49 0.9400 . ?
C50 C61 1.418(15) . ?
C50 C51 1.433(18) . ?
C51 C52 1.30(2) . ?
C51 H51 0.9400 . ?
C52 C53 1.424(18) . ?
C52 H52 0.9400 . ?
C53 C54 1.423(18) . ?
C53 C62 1.439(16) . ?
C54 C55 1.38(2) . ?
C54 H54 0.9400 . ?
C55 C56 1.40(2) . ?
C55 H55 0.9400 . ?
C56 C57 1.358(17) . ?
C56 H56 0.9400 . ?
C57 C62 1.412(16) . ?
C57 C58 1.451(16) . ?
C58 C59 1.324(16) . ?
C58 H58 0.9400 . ?
C59 C60 1.445(16) . ?
C59 H59 0.9400 . ?
C60 C61 1.412(15) . ?
C61 C62 1.448(15) . ?
C63 H63A 0.9700 . ?
C63 H63B 0.9700 . ?
C63 H63C 0.9700 . ?
C64 C65 1.35(2) . ?
C64 C84 1.39(3) . ?
C65 C66 1.42(2) . ?
C65 H65 0.9400 . ?
C66 C67 1.353(19) . ?
C66 C68 1.467(19) . ?
C67 H67 0.9400 . ?
C68 C69 1.402(19) . ?
C68 C81 1.430(16) . ?
C69 C70 1.38(2) . ?
C69 H69 0.9400 . ?
C70 C71 1.395(19) . ?
C70 H70 0.9400 . ?
C71 C82 1.397(17) . ?
C71 C72 1.414(18) . ?
C72 C73 1.32(2) . ?
C72 H72 0.9400 . ?
C73 C74 1.461(19) . ?
C73 H73 0.9400 . ?
C74 C75 1.39(2) . ?
C74 C83 1.408(16) . ?
C75 C76 1.42(3) . ?
C75 H75 0.9400 . ?
C76 C77 1.35(2) . ?
C76 H76 0.9400 . ?
C77 C78 1.375(16) . ?
C77 H77 0.9400 . ?
C78 C79 1.405(16) . ?
C78 C83 1.479(16) . ?
C79 C80 1.345(16) . ?
C79 H79 0.9400 . ?
C80 C81 1.419(18) . ?
C80 H80 0.9400 . ?
C81 C82 1.442(16) . ?
C82 C83 1.412(16) . ?
C84 H84A 0.9700 . ?
C84 H84B 0.9700 . ?
C84 H84C 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
C4 S1 C1 92.7(7) . . ?
C22 S2 C25 92.6(6) . . ?
C43 S3 C46 93.5(7) . . ?
C67 S4 C64 91.7(9) . . ?
C2 C1 C21 126.0(12) . . ?
C2 C1 S1 110.5(10) . . ?
C21 C1 S1 123.4(10) . . ?
C1 C2 C3 114.6(11) . . ?
C1 C2 H2 122.7 . . ?
C3 C2 H2 122.7 . . ?
C4 C3 C5 126.5(13) . . ?
C4 C3 C2 107.1(12) . . ?
C5 C3 C2 126.3(10) . . ?
C3 C4 S1 114.9(12) . . ?
C3 C4 H4 122.5 . . ?
S1 C4 H4 122.5 . . ?
C18 C5 C6 116.0(11) . . ?
C18 C5 C3 125.2(12) . . ?
C6 C5 C3 118.8(11) . . ?
C7 C6 C5 123.2(12) . . ?
C7 C6 H6 118.4 . . ?
C5 C6 H6 118.4 . . ?
C6 C7 C8 120.9(11) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C9 C8 C7 123.4(11) . . ?
C9 C8 C19 119.2(11) . . ?
C7 C8 C19 117.4(10) . . ?
C10 C9 C8 122.2(11) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C9 C10 C11 122.5(10) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C12 C11 C10 125.7(11) . . ?
C12 C11 C20 117.7(11) . . ?
C10 C11 C20 116.6(11) . . ?
C13 C12 C11 122.8(12) . . ?
C13 C12 H12 118.6 . . ?
C11 C12 H12 118.6 . . ?
C12 C13 C14 121.6(12) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C15 C14 C13 118.3(11) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C14 C15 C20 120.8(10) . . ?
C14 C15 C16 121.3(10) . . ?
C20 C15 C16 118.0(9) . . ?
C17 C16 C15 122.1(10) . . ?
C17 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
C16 C17 C18 121.2(10) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C19 C18 C5 121.4(11) . . ?
C19 C18 C17 117.7(10) . . ?
C5 C18 C17 120.9(10) . . ?
C18 C19 C8 120.7(10) . . ?
C18 C19 C20 119.9(10) . . ?
C8 C19 C20 119.3(10) . . ?
C15 C20 C19 121.0(10) . . ?
C15 C20 C11 118.8(10) . . ?
C19 C20 C11 120.2(10) . . ?
C1 C21 H21A 109.5 . . ?
C1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C42 128.1(13) . . ?
C23 C22 S2 110.3(9) . . ?
C42 C22 S2 121.3(10) . . ?
C22 C23 C24 114.9(11) . . ?
C22 C23 H23 122.5 . . ?
C24 C23 H23 122.5 . . ?
C25 C24 C23 111.2(11) . . ?
C25 C24 C26 121.7(11) . . ?
C23 C24 C26 126.9(10) . . ?
C24 C25 S2 110.9(11) . . ?
C24 C25 H25 124.6 . . ?
S2 C25 H25 124.6 . . ?
C27 C26 C39 119.8(11) . . ?
C27 C26 C24 118.0(10) . . ?
C39 C26 C24 121.9(12) . . ?
C26 C27 C28 121.3(11) . . ?
C26 C27 H27 119.4 . . ?
C28 C27 H27 119.4 . . ?
C29 C28 C27 120.6(12) . . ?
C29 C28 H28 119.7 . . ?
C27 C28 H28 119.7 . . ?
C28 C29 C40 118.7(11) . . ?
C28 C29 C30 123.3(11) . . ?
C40 C29 C30 118.0(11) . . ?
C31 C30 C29 123.8(12) . . ?
C31 C30 H30 118.1 . . ?
C29 C30 H30 118.1 . . ?
C30 C31 C32 119.9(11) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C33 C32 C31 122.2(11) . . ?
C33 C32 C41 118.0(10) . . ?
C31 C32 C41 119.8(10) . . ?
C32 C33 C34 122.6(11) . . ?
C32 C33 H33 118.7 . . ?
C34 C33 H33 118.7 . . ?
C35 C34 C33 118.7(12) . . ?
C35 C34 H34 120.6 . . ?
C33 C34 H34 120.6 . . ?
C34 C35 C36 122.8(12) . . ?
C34 C35 H35 118.6 . . ?
C36 C35 H35 118.6 . . ?
C37 C36 C35 126.4(11) . . ?
C37 C36 C41 115.8(10) . . ?
C35 C36 C41 117.8(11) . . ?
C38 C37 C36 124.4(11) . . ?
C38 C37 H37 117.8 . . ?
C36 C37 H37 117.8 . . ?
C37 C38 C39 121.2(10) . . ?
C37 C38 H38 119.4 . . ?
C39 C38 H38 119.4 . . ?
C26 C39 C38 123.2(11) . . ?
C26 C39 C40 118.4(11) . . ?
C38 C39 C40 118.2(10) . . ?
C29 C40 C41 120.6(10) . . ?
C29 C40 C39 121.1(10) . . ?
C41 C40 C39 118.3(10) . . ?
C40 C41 C36 122.0(10) . . ?
C40 C41 C32 117.9(10) . . ?
C36 C41 C32 120.0(9) . . ?
C22 C42 H42A 109.5 . . ?
C22 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C22 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C44 C43 C63 127.5(14) . . ?
C44 C43 S3 109.9(12) . . ?
C63 C43 S3 122.5(11) . . ?
C43 C44 C45 115.6(12) . . ?
C43 C44 H44 122.2 . . ?
C45 C44 H44 122.2 . . ?
C46 C45 C44 110.1(13) . . ?
C46 C45 C47 122.4(15) . . ?
C44 C45 C47 127.5(10) . . ?
C45 C46 S3 110.8(14) . . ?
C45 C46 H46 124.6 . . ?
S3 C46 H46 124.6 . . ?
C60 C47 C48 118.6(11) . . ?
C60 C47 C45 121.5(11) . . ?
C48 C47 C45 119.7(11) . . ?
C49 C48 C47 122.3(11) . . ?
C49 C48 H48 118.9 . . ?
C47 C48 H48 118.9 . . ?
C48 C49 C50 120.1(11) . . ?
C48 C49 H49 120.0 . . ?
C50 C49 H49 120.0 . . ?
C49 C50 C61 118.7(11) . . ?
C49 C50 C51 121.3(12) . . ?
C61 C50 C51 120.0(11) . . ?
C52 C51 C50 120.2(13) . . ?
C52 C51 H51 119.9 . . ?
C50 C51 H51 119.9 . . ?
C51 C52 C53 124.5(12) . . ?
C51 C52 H52 117.8 . . ?
C53 C52 H52 117.8 . . ?
C54 C53 C52 123.8(12) . . ?
C54 C53 C62 118.7(11) . . ?
C52 C53 C62 117.5(11) . . ?
C55 C54 C53 119.4(11) . . ?
C55 C54 H54 120.3 . . ?
C53 C54 H54 120.3 . . ?
C54 C55 C56 121.0(12) . . ?
C54 C55 H55 119.5 . . ?
C56 C55 H55 119.5 . . ?
C57 C56 C55 121.1(14) . . ?
C57 C56 H56 119.4 . . ?
C55 C56 H56 119.4 . . ?
C56 C57 C62 120.5(11) . . ?
C56 C57 C58 124.0(12) . . ?
C62 C57 C58 115.5(10) . . ?
C59 C58 C57 123.1(11) . . ?
C59 C58 H58 118.5 . . ?
C57 C58 H58 118.5 . . ?
C58 C59 C60 123.0(10) . . ?
C58 C59 H59 118.5 . . ?
C60 C59 H59 118.5 . . ?
C47 C60 C61 119.3(10) . . ?
C47 C60 C59 124.2(10) . . ?
C61 C60 C59 116.5(9) . . ?
C60 C61 C50 121.0(10) . . ?
C60 C61 C62 120.2(10) . . ?
C50 C61 C62 118.9(10) . . ?
C57 C62 C53 119.2(10) . . ?
C57 C62 C61 121.8(9) . . ?
C53 C62 C61 119.0(10) . . ?
C43 C63 H63A 109.5 . . ?
C43 C63 H63B 109.5 . . ?
H63A C63 H63B 109.5 . . ?
C43 C63 H63C 109.5 . . ?
H63A C63 H63C 109.5 . . ?
H63B C63 H63C 109.5 . . ?
C65 C64 C84 135(2) . . ?
C65 C64 S4 106.2(17) . . ?
C84 C64 S4 119.1(14) . . ?
C64 C65 C66 118.5(16) . . ?
C64 C65 H65 120.7 . . ?
C66 C65 H65 120.7 . . ?
C67 C66 C65 107.4(15) . . ?
C67 C66 C68 124.8(16) . . ?
C65 C66 C68 127.5(12) . . ?
C66 C67 S4 116.1(16) . . ?
C66 C67 H67 121.9 . . ?
S4 C67 H67 121.9 . . ?
C69 C68 C81 119.0(11) . . ?
C69 C68 C66 119.5(12) . . ?
C81 C68 C66 121.4(12) . . ?
C70 C69 C68 121.5(12) . . ?
C70 C69 H69 119.2 . . ?
C68 C69 H69 119.2 . . ?
C69 C70 C71 121.2(13) . . ?
C69 C70 H70 119.4 . . ?
C71 C70 H70 119.4 . . ?
C70 C71 C82 119.0(12) . . ?
C70 C71 C72 123.4(13) . . ?
C82 C71 C72 117.6(12) . . ?
C73 C72 C71 124.4(13) . . ?
C73 C72 H72 117.8 . . ?
C71 C72 H72 117.8 . . ?
C72 C73 C74 119.8(12) . . ?
C72 C73 H73 120.1 . . ?
C74 C73 H73 120.1 . . ?
C75 C74 C83 120.7(12) . . ?
C75 C74 C73 122.5(12) . . ?
C83 C74 C73 116.8(11) . . ?
C74 C75 C76 119.8(12) . . ?
C74 C75 H75 120.1 . . ?
C76 C75 H75 120.1 . . ?
C77 C76 C75 119.9(12) . . ?
C77 C76 H76 120.0 . . ?
C75 C76 H76 120.0 . . ?
C76 C77 C78 123.2(13) . . ?
C76 C77 H77 118.4 . . ?
C78 C77 H77 118.4 . . ?
C77 C78 C79 124.6(12) . . ?
C77 C78 C83 118.3(11) . . ?
C79 C78 C83 117.1(10) . . ?
C80 C79 C78 122.4(11) . . ?
C80 C79 H79 118.8 . . ?
C78 C79 H79 118.8 . . ?
C79 C80 C81 122.4(10) . . ?
C79 C80 H80 118.8 . . ?
C81 C80 H80 118.8 . . ?
C80 C81 C68 123.4(11) . . ?
C80 C81 C82 118.5(10) . . ?
C68 C81 C82 118.0(11) . . ?
C71 C82 C83 119.7(11) . . ?
C71 C82 C81 121.0(12) . . ?
C83 C82 C81 119.2(11) . . ?
C74 C83 C82 121.7(11) . . ?
C74 C83 C78 118.1(10) . . ?
C82 C83 C78 120.2(10) . . ?
C64 C84 H84A 109.5 . . ?
C64 C84 H84B 109.5 . . ?
H84A C84 H84B 109.5 . . ?
C64 C84 H84C 109.5 . . ?
H84A C84 H84C 109.5 . . ?
H84B C84 H84C 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
C4 S1 C1 C2 2.2(10) . . . . ?
C4 S1 C1 C21 -178.7(12) . . . . ?
C21 C1 C2 C3 176.7(12) . . . . ?
S1 C1 C2 C3 -4.2(13) . . . . ?
C1 C2 C3 C4 4.3(15) . . . . ?
C1 C2 C3 C5 -174.1(11) . . . . ?
C5 C3 C4 S1 175.8(10) . . . . ?
C2 C3 C4 S1 -2.6(15) . . . . ?
C1 S1 C4 C3 0.4(12) . . . . ?
C4 C3 C5 C18 138.7(14) . . . . ?
C2 C3 C5 C18 -43.2(17) . . . . ?
C4 C3 C5 C6 -43.8(17) . . . . ?
C2 C3 C5 C6 134.3(13) . . . . ?
C18 C5 C6 C7 7.1(17) . . . . ?
C3 C5 C6 C7 -170.6(11) . . . . ?
C5 C6 C7 C8 -3.8(18) . . . . ?
C6 C7 C8 C9 -179.4(10) . . . . ?
C6 C7 C8 C19 -0.7(15) . . . . ?
C7 C8 C9 C10 177.0(10) . . . . ?
C19 C8 C9 C10 -1.7(15) . . . . ?
C8 C9 C10 C11 1.8(17) . . . . ?
C9 C10 C11 C12 179.0(11) . . . . ?
C9 C10 C11 C20 -1.2(16) . . . . ?
C10 C11 C12 C13 178.9(12) . . . . ?
C20 C11 C12 C13 -0.9(18) . . . . ?
C11 C12 C13 C14 1(2) . . . . ?
C12 C13 C14 C15 -1.4(19) . . . . ?
C13 C14 C15 C20 1.1(16) . . . . ?
C13 C14 C15 C16 -179.0(10) . . . . ?
C14 C15 C16 C17 -178.9(9) . . . . ?
C20 C15 C16 C17 1.0(14) . . . . ?
C15 C16 C17 C18 -1.2(14) . . . . ?
C6 C5 C18 C19 -6.2(15) . . . . ?
C3 C5 C18 C19 171.4(9) . . . . ?
C6 C5 C18 C17 175.5(9) . . . . ?
C3 C5 C18 C17 -7.0(15) . . . . ?
C16 C17 C18 C19 0.8(13) . . . . ?
C16 C17 C18 C5 179.2(9) . . . . ?
C5 C18 C19 C8 2.2(14) . . . . ?
C17 C18 C19 C8 -179.4(8) . . . . ?
C5 C18 C19 C20 -178.8(8) . . . . ?
C17 C18 C19 C20 -0.3(13) . . . . ?
C9 C8 C19 C18 -179.8(9) . . . . ?
C7 C8 C19 C18 1.5(13) . . . . ?
C9 C8 C19 C20 1.1(13) . . . . ?
C7 C8 C19 C20 -177.6(9) . . . . ?
C14 C15 C20 C19 179.4(8) . . . . ?
C16 C15 C20 C19 -0.5(13) . . . . ?
C14 C15 C20 C11 -0.6(14) . . . . ?
C16 C15 C20 C11 179.5(8) . . . . ?
C18 C19 C20 C15 0.2(13) . . . . ?
C8 C19 C20 C15 179.3(8) . . . . ?
C18 C19 C20 C11 -179.8(8) . . . . ?
C8 C19 C20 C11 -0.7(13) . . . . ?
C12 C11 C20 C15 0.5(15) . . . . ?
C10 C11 C20 C15 -179.3(9) . . . . ?
C12 C11 C20 C19 -179.5(9) . . . . ?
C10 C11 C20 C19 0.7(14) . . . . ?
C25 S2 C22 C23 3.4(11) . . . . ?
C25 S2 C22 C42 177.3(13) . . . . ?
C42 C22 C23 C24 -176.5(14) . . . . ?
S2 C22 C23 C24 -3.2(15) . . . . ?
C22 C23 C24 C25 1.0(16) . . . . ?
C22 C23 C24 C26 176.1(12) . . . . ?
C23 C24 C25 S2 1.6(14) . . . . ?
C26 C24 C25 S2 -173.7(9) . . . . ?
C22 S2 C25 C24 -2.9(11) . . . . ?
C25 C24 C26 C27 47.1(16) . . . . ?
C23 C24 C26 C27 -127.4(13) . . . . ?
C25 C24 C26 C39 -138.6(12) . . . . ?
C23 C24 C26 C39 46.8(17) . . . . ?
C39 C26 C27 C28 0.0(17) . . . . ?
C24 C26 C27 C28 174.4(11) . . . . ?
C26 C27 C28 C29 -1.2(18) . . . . ?
C27 C28 C29 C40 2.6(16) . . . . ?
C27 C28 C29 C30 -179.4(10) . . . . ?
C28 C29 C30 C31 -177.5(11) . . . . ?
C40 C29 C30 C31 0.4(16) . . . . ?
C29 C30 C31 C32 0.7(17) . . . . ?
C30 C31 C32 C33 178.6(11) . . . . ?
C30 C31 C32 C41 -1.5(15) . . . . ?
C31 C32 C33 C34 179.9(12) . . . . ?
C41 C32 C33 C34 0.0(18) . . . . ?
C32 C33 C34 C35 3(2) . . . . ?
C33 C34 C35 C36 -2.7(18) . . . . ?
C34 C35 C36 C37 -179.1(11) . . . . ?
C34 C35 C36 C41 0.1(16) . . . . ?
C35 C36 C37 C38 178.6(10) . . . . ?
C41 C36 C37 C38 -0.6(15) . . . . ?
C36 C37 C38 C39 1.2(17) . . . . ?
C27 C26 C39 C38 -175.2(10) . . . . ?
C24 C26 C39 C38 10.6(17) . . . . ?
C27 C26 C39 C40 -0.2(16) . . . . ?
C24 C26 C39 C40 -174.4(10) . . . . ?
C37 C38 C39 C26 175.8(10) . . . . ?
C37 C38 C39 C40 0.8(15) . . . . ?
C28 C29 C40 C41 177.3(10) . . . . ?
C30 C29 C40 C41 -0.8(14) . . . . ?
C28 C29 C40 C39 -2.8(15) . . . . ?
C30 C29 C40 C39 179.1(9) . . . . ?
C26 C39 C40 C29 1.6(15) . . . . ?
C38 C39 C40 C29 176.9(9) . . . . ?
C26 C39 C40 C41 -178.5(9) . . . . ?
C38 C39 C40 C41 -3.2(14) . . . . ?
C29 C40 C41 C36 -176.2(9) . . . . ?
C39 C40 C41 C36 3.9(14) . . . . ?
C29 C40 C41 C32 0.0(14) . . . . ?
C39 C40 C41 C32 -179.9(9) . . . . ?
C37 C36 C41 C40 -2.0(13) . . . . ?
C35 C36 C41 C40 178.8(9) . . . . ?
C37 C36 C41 C32 -178.1(9) . . . . ?
C35 C36 C41 C32 2.6(13) . . . . ?
C33 C32 C41 C40 -178.9(10) . . . . ?
C31 C32 C41 C40 1.2(14) . . . . ?
C33 C32 C41 C36 -2.6(14) . . . . ?
C31 C32 C41 C36 177.5(9) . . . . ?
C46 S3 C43 C44 -0.5(11) . . . . ?
C46 S3 C43 C63 -176.6(14) . . . . ?
C63 C43 C44 C45 174.1(15) . . . . ?
S3 C43 C44 C45 -1.8(14) . . . . ?
C43 C44 C45 C46 3.9(16) . . . . ?
C43 C44 C45 C47 -174.5(11) . . . . ?
C44 C45 C46 S3 -4.0(15) . . . . ?
C47 C45 C46 S3 174.5(10) . . . . ?
C43 S3 C46 C45 2.7(12) . . . . ?
C46 C45 C47 C60 137.8(13) . . . . ?
C44 C45 C47 C60 -44.0(16) . . . . ?
C46 C45 C47 C48 -47.7(16) . . . . ?
C44 C45 C47 C48 130.5(13) . . . . ?
C60 C47 C48 C49 -0.6(16) . . . . ?
C45 C47 C48 C49 -175.3(10) . . . . ?
C47 C48 C49 C50 4.3(17) . . . . ?
C48 C49 C50 C61 -5.2(16) . . . . ?
C48 C49 C50 C51 177.5(11) . . . . ?
C49 C50 C51 C52 177.4(12) . . . . ?
C61 C50 C51 C52 0.2(19) . . . . ?
C50 C51 C52 C53 0(2) . . . . ?
C51 C52 C53 C54 178.9(13) . . . . ?
C51 C52 C53 C62 -0.5(19) . . . . ?
C52 C53 C54 C55 176.6(12) . . . . ?
C62 C53 C54 C55 -4.0(18) . . . . ?
C53 C54 C55 C56 4(2) . . . . ?
C54 C55 C56 C57 -3(2) . . . . ?
C55 C56 C57 C62 1.1(17) . . . . ?
C55 C56 C57 C58 -180.0(11) . . . . ?
C56 C57 C58 C59 -179.3(10) . . . . ?
C62 C57 C58 C59 -0.3(15) . . . . ?
C57 C58 C59 C60 0.6(16) . . . . ?
C48 C47 C60 C61 -1.9(14) . . . . ?
C45 C47 C60 C61 172.7(9) . . . . ?
C48 C47 C60 C59 176.7(9) . . . . ?
C45 C47 C60 C59 -8.8(15) . . . . ?
C58 C59 C60 C47 -179.9(9) . . . . ?
C58 C59 C60 C61 -1.3(14) . . . . ?
C47 C60 C61 C50 0.8(14) . . . . ?
C59 C60 C61 C50 -177.9(9) . . . . ?
C47 C60 C61 C62 -179.7(8) . . . . ?
C59 C60 C61 C62 1.7(13) . . . . ?
C49 C50 C61 C60 2.8(14) . . . . ?
C51 C50 C61 C60 -179.9(10) . . . . ?
C49 C50 C61 C62 -176.8(9) . . . . ?
C51 C50 C61 C62 0.5(14) . . . . ?
C56 C57 C62 C53 -1.0(15) . . . . ?
C58 C57 C62 C53 180.0(9) . . . . ?
C56 C57 C62 C61 179.8(10) . . . . ?
C58 C57 C62 C61 0.7(13) . . . . ?
C54 C53 C62 C57 2.5(15) . . . . ?
C52 C53 C62 C57 -178.1(10) . . . . ?
C54 C53 C62 C61 -178.3(9) . . . . ?
C52 C53 C62 C61 1.1(14) . . . . ?
C60 C61 C62 C57 -1.5(14) . . . . ?
C50 C61 C62 C57 178.0(9) . . . . ?
C60 C61 C62 C53 179.2(9) . . . . ?
C50 C61 C62 C53 -1.2(13) . . . . ?
C67 S4 C64 C65 1.1(15) . . . . ?
C67 S4 C64 C84 -178.7(18) . . . . ?
C84 C64 C65 C66 179(2) . . . . ?
S4 C64 C65 C66 -1(2) . . . . ?
C64 C65 C66 C67 0(2) . . . . ?
C64 C65 C66 C68 173.9(15) . . . . ?
C65 C66 C67 S4 1.4(18) . . . . ?
C68 C66 C67 S4 -173.2(11) . . . . ?
C64 S4 C67 C66 -1.5(15) . . . . ?
C67 C66 C68 C69 44.3(19) . . . . ?
C65 C66 C68 C69 -129.2(15) . . . . ?
C67 C66 C68 C81 -138.2(15) . . . . ?
C65 C66 C68 C81 48.3(19) . . . . ?
C81 C68 C69 C70 0.2(18) . . . . ?
C66 C68 C69 C70 177.7(11) . . . . ?
C68 C69 C70 C71 -3.6(18) . . . . ?
C69 C70 C71 C82 5.1(17) . . . . ?
C69 C70 C71 C72 -178.8(11) . . . . ?
C70 C71 C72 C73 -177.3(12) . . . . ?
C82 C71 C72 C73 -1.2(18) . . . . ?
C71 C72 C73 C74 3(2) . . . . ?
C72 C73 C74 C75 177.8(12) . . . . ?
C72 C73 C74 C83 -1.5(17) . . . . ?
C83 C74 C75 C76 -2.4(17) . . . . ?
C73 C74 C75 C76 178.4(11) . . . . ?
C74 C75 C76 C77 1.8(18) . . . . ?
C75 C76 C77 C78 -0.8(18) . . . . ?
C76 C77 C78 C79 178.7(10) . . . . ?
C76 C77 C78 C83 0.5(16) . . . . ?
C77 C78 C79 C80 178.5(11) . . . . ?
C83 C78 C79 C80 -3.2(15) . . . . ?
C78 C79 C80 C81 2.3(18) . . . . ?
C79 C80 C81 C68 177.7(11) . . . . ?
C79 C80 C81 C82 -0.8(16) . . . . ?
C69 C68 C81 C80 -177.0(10) . . . . ?
C66 C68 C81 C80 5.5(17) . . . . ?
C69 C68 C81 C82 1.5(16) . . . . ?
C66 C68 C81 C82 -176.0(9) . . . . ?
C70 C71 C82 C83 174.8(9) . . . . ?
C72 C71 C82 C83 -1.5(15) . . . . ?
C70 C71 C82 C81 -3.4(15) . . . . ?
C72 C71 C82 C81 -179.7(10) . . . . ?
C80 C81 C82 C71 178.7(10) . . . . ?
C68 C81 C82 C71 0.1(15) . . . . ?
C80 C81 C82 C83 0.5(14) . . . . ?
C68 C81 C82 C83 -178.1(9) . . . . ?
C75 C74 C83 C82 179.7(9) . . . . ?
C73 C74 C83 C82 -1.0(15) . . . . ?
C75 C74 C83 C78 2.0(15) . . . . ?
C73 C74 C83 C78 -178.8(9) . . . . ?
C71 C82 C83 C74 2.5(15) . . . . ?
C81 C82 C83 C74 -179.3(9) . . . . ?
C71 C82 C83 C78 -179.8(9) . . . . ?
C81 C82 C83 C78 -1.6(14) . . . . ?
C77 C78 C83 C74 -1.0(14) . . . . ?
C79 C78 C83 C74 -179.4(9) . . . . ?
C77 C78 C83 C82 -178.8(9) . . . . ?
C79 C78 C83 C82 2.8(13) . . . . ?

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

#==============================================================================
# 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        2-Methyl-4-(pyren-1-yl)thiophene
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_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_mina239_2b
_database_code_depnum_ccdc_archive 'CCDC 1947302'
loop_
_audit_author_name
_audit_author_address
'Suguru Ito'
;Yokohama National University
Japan
;
_audit_update_record             
;
2019-08-15 deposited with the CCDC.	2019-09-12 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C44 H32 S2'
_chemical_formula_moiety         'C44 H32 S2'
_chemical_formula_weight         624.86
_chemical_melting_point          364.15-365.15

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   8.32033(14)
_cell_length_b                   7.16490(12)
_cell_length_c                   53.8962(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.3805(13)
_cell_angle_gamma                90.0000
_cell_volume                     3207.40(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8524
_cell_measurement_theta_min      5.33
_cell_measurement_theta_max      72.77
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.653
_exptl_crystal_size_mid          0.476
_exptl_crystal_size_min          0.223
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312.00
_exptl_absorpt_coefficient_mu    1.735
_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  0.420
_exptl_absorpt_correction_T_max  0.679

#==============================================================================
# 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            16899
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_theta_max         68.249
_diffrn_reflns_theta_min         4.932
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -64
_diffrn_reflns_limit_l_max       60
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5854
_reflns_number_gt                4825
_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          0.0914
_refine_ls_R_factor_gt           0.0811
_refine_ls_wR_factor_ref         0.2095
_refine_ls_wR_factor_gt          0.2020
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         5854
_refine_ls_number_parameters     415
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0799P)²+4.6233P] 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         1.12
_refine_diff_density_min         -0.82
_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)
;
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 0.58083(15) -0.01599(19) 0.96043(2) 0.0853(4) Uani 1 1 d . . . . .
S2 S -0.11619(16) 0.4977(2) 0.95914(2) 0.0904(4) Uani 1 1 d . . . . .
C1 C 0.4613(5) -0.1834(6) 0.94576(6) 0.0671(10) Uani 1 1 d . . . . .
C2 C 0.4241(4) -0.1309(5) 0.92192(6) 0.0549(8) Uani 1 1 d . . . . .
H2 H 0.3606 -0.2046 0.9107 0.066 Uiso 1 1 calc R U . . .
C3 C 0.4892(4) 0.0457(5) 0.91513(6) 0.0524(8) Uani 1 1 d . . . . .
C4 C 0.5785(5) 0.1231(6) 0.93437(7) 0.0696(11) Uani 1 1 d . . . . .
H4 H 0.6322 0.2382 0.9336 0.083 Uiso 1 1 calc R U . . .
C5 C 0.4528(4) 0.1419(5) 0.89092(6) 0.0456(7) Uani 1 1 d . . . . .
C6 C 0.3909(4) 0.3228(5) 0.89109(7) 0.0540(8) Uani 1 1 d . . . . .
H6 H 0.3810 0.3832 0.9064 0.065 Uiso 1 1 calc R U . . .
C7 C 0.3439(4) 0.4157(5) 0.86941(7) 0.0536(8) Uani 1 1 d . . . . .
H7 H 0.3028 0.5376 0.8702 0.064 Uiso 1 1 calc R U . . .
C8 C 0.3564(3) 0.3318(4) 0.84649(6) 0.0439(7) Uani 1 1 d . . . . .
C9 C 0.3071(4) 0.4221(5) 0.82350(7) 0.0520(8) Uani 1 1 d . . . . .
H9 H 0.2648 0.5436 0.8239 0.062 Uiso 1 1 calc R U . . .
C10 C 0.3197(4) 0.3386(5) 0.80160(7) 0.0517(8) Uani 1 1 d . . . . .
H10 H 0.2837 0.4014 0.7870 0.062 Uiso 1 1 calc R U . . .
C11 C 0.3872(3) 0.1546(4) 0.79985(6) 0.0437(7) Uani 1 1 d . . . . .
C12 C 0.4018(4) 0.0638(5) 0.77725(6) 0.0542(8) Uani 1 1 d . . . . .
H12 H 0.3643 0.1227 0.7624 0.065 Uiso 1 1 calc R U . . .
C13 C 0.4704(4) -0.1106(5) 0.77624(6) 0.0553(8) Uani 1 1 d . . . . .
H13 H 0.4804 -0.1685 0.7608 0.066 Uiso 1 1 calc R U . . .
C14 C 0.5249(4) -0.2023(5) 0.79786(6) 0.0484(7) Uani 1 1 d . . . . .
H14 H 0.5720 -0.3211 0.7969 0.058 Uiso 1 1 calc R U . . .
C15 C 0.5102(3) -0.1191(4) 0.82098(5) 0.0399(6) Uani 1 1 d . . . . .
C16 C 0.5619(3) -0.2089(4) 0.84374(5) 0.0414(7) Uani 1 1 d . . . . .
H16 H 0.6090 -0.3280 0.8432 0.050 Uiso 1 1 calc R U . . .
C17 C 0.5451(3) -0.1279(4) 0.86597(5) 0.0413(7) Uani 1 1 d . . . . .
H17 H 0.5812 -0.1913 0.8805 0.050 Uiso 1 1 calc R U . . .
C18 C 0.4728(3) 0.0540(4) 0.86797(5) 0.0372(6) Uani 1 1 d . . . . .
C19 C 0.4234(3) 0.1488(4) 0.84563(5) 0.0374(6) Uani 1 1 d . . . . .
C20 C 0.4403(3) 0.0622(4) 0.82216(5) 0.0373(6) Uani 1 1 d . . . . .
C21 C 0.4078(7) -0.3602(7) 0.95878(8) 0.0908(15) Uani 1 1 d . . . . .
H21A H 0.3240 -0.4210 0.9481 0.109 Uiso 1 1 calc R U . . .
H21B H 0.4996 -0.4458 0.9605 0.109 Uiso 1 1 calc R U . . .
C22 C 0.3470(11) -0.3332(10) 0.98283(11) 0.156(3) Uani 1 1 d . . . . .
H22A H 0.3164 -0.4528 0.9896 0.187 Uiso 1 1 calc R U . . .
H22B H 0.4297 -0.2767 0.9938 0.187 Uiso 1 1 calc R U . . .
H22C H 0.2537 -0.2519 0.9814 0.187 Uiso 1 1 calc R U . . .
C23 C -0.0090(5) 0.3248(7) 0.94494(7) 0.0719(11) Uani 1 1 d . . . . .
C24 C 0.0104(4) 0.3746(5) 0.92094(6) 0.0562(9) Uani 1 1 d . . . . .
H24 H 0.0644 0.2988 0.9099 0.067 Uiso 1 1 calc R U . . .
C25 C -0.0577(4) 0.5514(5) 0.91382(6) 0.0513(8) Uani 1 1 d . . . . .
C26 C -0.1318(5) 0.6334(6) 0.93275(7) 0.0688(11) Uani 1 1 d . . . . .
H26 H -0.1849 0.7491 0.9316 0.083 Uiso 1 1 calc R U . . .
C27 C -0.0401(3) 0.6424(4) 0.88933(5) 0.0422(7) Uani 1 1 d . . . . .
C28 C 0.0233(4) 0.8236(5) 0.88889(6) 0.0506(8) Uani 1 1 d . . . . .
H28 H 0.0469 0.8860 0.9040 0.061 Uiso 1 1 calc R U . . .
C29 C 0.0519(4) 0.9131(5) 0.86692(7) 0.0508(8) Uani 1 1 d . . . . .
H29 H 0.0943 1.0348 0.8673 0.061 Uiso 1 1 calc R U . . .
C30 C 0.0191(3) 0.8260(4) 0.84427(6) 0.0422(7) Uani 1 1 d . . . . .
C31 C 0.0491(4) 0.9135(5) 0.82101(7) 0.0504(8) Uani 1 1 d . . . . .
H31 H 0.0930 1.0345 0.8211 0.060 Uiso 1 1 calc R U . . .
C32 C 0.0166(4) 0.8278(5) 0.79936(6) 0.0514(8) Uani 1 1 d . . . . .
H32 H 0.0394 0.8891 0.7846 0.062 Uiso 1 1 calc R U . . .
C33 C -0.0530(3) 0.6432(4) 0.79806(5) 0.0433(7) Uani 1 1 d . . . . .
C34 C -0.0886(4) 0.5504(5) 0.77571(6) 0.0529(8) Uani 1 1 d . . . . .
H34 H -0.0662 0.6084 0.7607 0.063 Uiso 1 1 calc R U . . .
C35 C -0.1564(4) 0.3746(5) 0.77534(6) 0.0530(8) Uani 1 1 d . . . . .
H35 H -0.1799 0.3146 0.7600 0.064 Uiso 1 1 calc R U . . .
C36 C -0.1903(4) 0.2854(5) 0.79726(5) 0.0454(7) Uani 1 1 d . . . . .
H36 H -0.2370 0.1659 0.7967 0.055 Uiso 1 1 calc R U . . .
C37 C -0.1554(3) 0.3725(4) 0.82016(5) 0.0374(6) Uani 1 1 d . . . . .
C38 C -0.1880(3) 0.2852(4) 0.84327(5) 0.0391(6) Uani 1 1 d . . . . .
H38 H -0.2355 0.1661 0.8431 0.047 Uiso 1 1 calc R U . . .
C39 C -0.1522(3) 0.3696(4) 0.86517(5) 0.0388(6) Uani 1 1 d . . . . .
H39 H -0.1756 0.3081 0.8799 0.047 Uiso 1 1 calc R U . . .
C40 C -0.0790(3) 0.5513(4) 0.86663(5) 0.0367(6) Uani 1 1 d . . . . .
C41 C -0.0483(3) 0.6433(4) 0.84395(5) 0.0360(6) Uani 1 1 d . . . . .
C42 C -0.0856(3) 0.5526(4) 0.82079(5) 0.0361(6) Uani 1 1 d . . . . .
C43 C 0.0532(8) 0.1482(7) 0.95821(8) 0.1011(18) Uani 1 1 d . . . . .
H43A H -0.0385 0.0645 0.9601 0.121 Uiso 1 1 calc R U . . .
H43B H 0.1269 0.0851 0.9474 0.121 Uiso 1 1 calc R U . . .
C44 C 0.1325(12) 0.1722(11) 0.98158(13) 0.185(4) Uani 1 1 d . . . . .
H44A H 0.1664 0.0516 0.9882 0.222 Uiso 1 1 calc R U . . .
H44B H 0.2261 0.2511 0.9800 0.222 Uiso 1 1 calc R U . . .
H44C H 0.0601 0.2304 0.9927 0.222 Uiso 1 1 calc R U . . .


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

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

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.721(5) . ?
S1 C4 1.722(5) . ?
S2 C26 1.721(4) . ?
S2 C23 1.731(5) . ?
C1 C2 1.357(5) . ?
C1 C21 1.527(6) . ?
C2 C3 1.432(5) . ?
C2 H2 0.9400 . ?
C3 C4 1.358(5) . ?
C3 C5 1.491(5) . ?
C4 H4 0.9400 . ?
C5 C6 1.395(5) . ?
C5 C18 1.407(4) . ?
C6 C7 1.381(5) . ?
C6 H6 0.9400 . ?
C7 C8 1.383(5) . ?
C7 H7 0.9400 . ?
C8 C19 1.426(4) . ?
C8 C9 1.436(5) . ?
C9 C10 1.333(5) . ?
C9 H9 0.9400 . ?
C10 C11 1.439(5) . ?
C10 H10 0.9400 . ?
C11 C12 1.392(5) . ?
C11 C20 1.420(4) . ?
C12 C13 1.376(5) . ?
C12 H12 0.9400 . ?
C13 C14 1.390(5) . ?
C13 H13 0.9400 . ?
C14 C15 1.393(4) . ?
C14 H14 0.9400 . ?
C15 C20 1.426(4) . ?
C15 C16 1.429(4) . ?
C16 C17 1.346(4) . ?
C16 H16 0.9400 . ?
C17 C18 1.442(4) . ?
C17 H17 0.9400 . ?
C18 C19 1.422(4) . ?
C19 C20 1.424(4) . ?
C21 C22 1.432(7) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C23 C24 1.360(5) . ?
C23 C43 1.528(7) . ?
C24 C25 1.431(5) . ?
C24 H24 0.9400 . ?
C25 C26 1.357(5) . ?
C25 C27 1.487(4) . ?
C26 H26 0.9400 . ?
C27 C28 1.402(5) . ?
C27 C40 1.408(4) . ?
C28 C29 1.380(5) . ?
C28 H28 0.9400 . ?
C29 C30 1.384(4) . ?
C29 H29 0.9400 . ?
C30 C41 1.424(4) . ?
C30 C31 1.437(4) . ?
C31 C32 1.332(5) . ?
C31 H31 0.9400 . ?
C32 C33 1.444(5) . ?
C32 H32 0.9400 . ?
C33 C34 1.392(5) . ?
C33 C42 1.427(4) . ?
C34 C35 1.380(5) . ?
C34 H34 0.9400 . ?
C35 C36 1.386(4) . ?
C35 H35 0.9400 . ?
C36 C37 1.399(4) . ?
C36 H36 0.9400 . ?
C37 C42 1.414(4) . ?
C37 C38 1.434(4) . ?
C38 C39 1.344(4) . ?
C38 H38 0.9400 . ?
C39 C40 1.437(4) . ?
C39 H39 0.9400 . ?
C40 C41 1.425(4) . ?
C41 C42 1.425(4) . ?
C43 C44 1.398(7) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C44 H44C 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
C1 S1 C4 92.88(19) . . ?
C26 S2 C23 93.13(19) . . ?
C2 C1 C21 127.5(4) . . ?
C2 C1 S1 109.6(3) . . ?
C21 C1 S1 122.9(3) . . ?
C1 C2 C3 114.7(3) . . ?
C1 C2 H2 122.6 . . ?
C3 C2 H2 122.6 . . ?
C4 C3 C2 111.4(3) . . ?
C4 C3 C5 123.6(4) . . ?
C2 C3 C5 124.9(3) . . ?
C3 C4 S1 111.4(3) . . ?
C3 C4 H4 124.3 . . ?
S1 C4 H4 124.3 . . ?
C6 C5 C18 119.0(3) . . ?
C6 C5 C3 118.7(3) . . ?
C18 C5 C3 122.3(3) . . ?
C7 C6 C5 121.9(3) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C8 120.9(3) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C19 118.6(3) . . ?
C7 C8 C9 122.8(3) . . ?
C19 C8 C9 118.6(3) . . ?
C10 C9 C8 121.9(3) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C10 C11 121.4(3) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C20 118.9(3) . . ?
C12 C11 C10 122.7(3) . . ?
C20 C11 C10 118.4(3) . . ?
C13 C12 C11 121.1(3) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 120.7(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C20 119.1(3) . . ?
C14 C15 C16 122.5(3) . . ?
C20 C15 C16 118.4(3) . . ?
C17 C16 C15 121.9(3) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C18 121.4(3) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C5 C18 C19 119.2(3) . . ?
C5 C18 C17 122.8(3) . . ?
C19 C18 C17 118.0(2) . . ?
C18 C19 C20 120.3(3) . . ?
C18 C19 C8 120.4(3) . . ?
C20 C19 C8 119.3(3) . . ?
C11 C20 C19 120.5(3) . . ?
C11 C20 C15 119.6(3) . . ?
C19 C20 C15 119.9(3) . . ?
C22 C21 C1 115.6(5) . . ?
C22 C21 H21A 108.4 . . ?
C1 C21 H21A 108.4 . . ?
C22 C21 H21B 108.4 . . ?
C1 C21 H21B 108.4 . . ?
H21A C21 H21B 107.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C43 127.3(4) . . ?
C24 C23 S2 109.0(3) . . ?
C43 C23 S2 123.7(3) . . ?
C23 C24 C25 114.9(4) . . ?
C23 C24 H24 122.6 . . ?
C25 C24 H24 122.6 . . ?
C26 C25 C24 111.8(3) . . ?
C26 C25 C27 123.4(4) . . ?
C24 C25 C27 124.6(3) . . ?
C25 C26 S2 111.2(3) . . ?
C25 C26 H26 124.4 . . ?
S2 C26 H26 124.4 . . ?
C28 C27 C40 118.8(3) . . ?
C28 C27 C25 118.5(3) . . ?
C40 C27 C25 122.6(3) . . ?
C29 C28 C27 121.9(3) . . ?
C29 C28 H28 119.0 . . ?
C27 C28 H28 119.0 . . ?
C28 C29 C30 120.8(3) . . ?
C28 C29 H29 119.6 . . ?
C30 C29 H29 119.6 . . ?
C29 C30 C41 118.9(3) . . ?
C29 C30 C31 122.5(3) . . ?
C41 C30 C31 118.7(3) . . ?
C32 C31 C30 121.7(3) . . ?
C32 C31 H31 119.1 . . ?
C30 C31 H31 119.1 . . ?
C31 C32 C33 121.7(3) . . ?
C31 C32 H32 119.2 . . ?
C33 C32 H32 119.2 . . ?
C34 C33 C42 118.9(3) . . ?
C34 C33 C32 122.9(3) . . ?
C42 C33 C32 118.1(3) . . ?
C35 C34 C33 121.0(3) . . ?
C35 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
C34 C35 C36 120.8(3) . . ?
C34 C35 H35 119.6 . . ?
C36 C35 H35 119.6 . . ?
C35 C36 C37 120.3(3) . . ?
C35 C36 H36 119.9 . . ?
C37 C36 H36 119.9 . . ?
C36 C37 C42 119.5(3) . . ?
C36 C37 C38 122.1(3) . . ?
C42 C37 C38 118.4(3) . . ?
C39 C38 C37 121.5(3) . . ?
C39 C38 H38 119.2 . . ?
C37 C38 H38 119.2 . . ?
C38 C39 C40 121.8(3) . . ?
C38 C39 H39 119.1 . . ?
C40 C39 H39 119.1 . . ?
C27 C40 C41 119.2(3) . . ?
C27 C40 C39 122.9(3) . . ?
C41 C40 C39 118.0(2) . . ?
C30 C41 C40 120.4(3) . . ?
C30 C41 C42 119.7(3) . . ?
C40 C41 C42 120.0(3) . . ?
C37 C42 C41 120.3(2) . . ?
C37 C42 C33 119.5(3) . . ?
C41 C42 C33 120.1(3) . . ?
C44 C43 C23 116.7(5) . . ?
C44 C43 H43A 108.1 . . ?
C23 C43 H43A 108.1 . . ?
C44 C43 H43B 108.1 . . ?
C23 C43 H43B 108.1 . . ?
H43A C43 H43B 107.3 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 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
C4 S1 C1 C2 0.3(3) . . . . ?
C4 S1 C1 C21 -179.1(4) . . . . ?
C21 C1 C2 C3 178.5(4) . . . . ?
S1 C1 C2 C3 -0.8(4) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C1 C2 C3 C5 -173.8(3) . . . . ?
C2 C3 C4 S1 -0.7(4) . . . . ?
C5 C3 C4 S1 174.2(3) . . . . ?
C1 S1 C4 C3 0.3(3) . . . . ?
C4 C3 C5 C6 -50.5(5) . . . . ?
C2 C3 C5 C6 123.7(4) . . . . ?
C4 C3 C5 C18 132.0(4) . . . . ?
C2 C3 C5 C18 -53.8(5) . . . . ?
C18 C5 C6 C7 2.2(5) . . . . ?
C3 C5 C6 C7 -175.4(3) . . . . ?
C5 C6 C7 C8 0.1(5) . . . . ?
C6 C7 C8 C19 -1.8(5) . . . . ?
C6 C7 C8 C9 179.2(3) . . . . ?
C7 C8 C9 C10 -179.8(3) . . . . ?
C19 C8 C9 C10 1.2(5) . . . . ?
C8 C9 C10 C11 -1.5(5) . . . . ?
C9 C10 C11 C12 180.0(3) . . . . ?
C9 C10 C11 C20 0.2(4) . . . . ?
C20 C11 C12 C13 -1.7(5) . . . . ?
C10 C11 C12 C13 178.5(3) . . . . ?
C11 C12 C13 C14 0.9(5) . . . . ?
C12 C13 C14 C15 0.4(5) . . . . ?
C13 C14 C15 C20 -0.8(4) . . . . ?
C13 C14 C15 C16 178.9(3) . . . . ?
C14 C15 C16 C17 -179.1(3) . . . . ?
C20 C15 C16 C17 0.6(4) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C6 C5 C18 C19 -2.6(4) . . . . ?
C3 C5 C18 C19 174.9(3) . . . . ?
C6 C5 C18 C17 176.1(3) . . . . ?
C3 C5 C18 C17 -6.4(4) . . . . ?
C16 C17 C18 C5 179.6(3) . . . . ?
C16 C17 C18 C19 -1.7(4) . . . . ?
C5 C18 C19 C20 -179.2(3) . . . . ?
C17 C18 C19 C20 2.1(4) . . . . ?
C5 C18 C19 C8 0.9(4) . . . . ?
C17 C18 C19 C8 -177.8(2) . . . . ?
C7 C8 C19 C18 1.3(4) . . . . ?
C9 C8 C19 C18 -179.6(3) . . . . ?
C7 C8 C19 C20 -178.6(3) . . . . ?
C9 C8 C19 C20 0.4(4) . . . . ?
C12 C11 C20 C19 -178.4(3) . . . . ?
C10 C11 C20 C19 1.4(4) . . . . ?
C12 C11 C20 C15 1.2(4) . . . . ?
C10 C11 C20 C15 -179.0(3) . . . . ?
C18 C19 C20 C11 178.4(2) . . . . ?
C8 C19 C20 C11 -1.7(4) . . . . ?
C18 C19 C20 C15 -1.2(4) . . . . ?
C8 C19 C20 C15 178.7(2) . . . . ?
C14 C15 C20 C11 0.0(4) . . . . ?
C16 C15 C20 C11 -179.7(3) . . . . ?
C14 C15 C20 C19 179.6(3) . . . . ?
C16 C15 C20 C19 -0.1(4) . . . . ?
C2 C1 C21 C22 -132.5(6) . . . . ?
S1 C1 C21 C22 46.7(7) . . . . ?
C26 S2 C23 C24 -0.3(3) . . . . ?
C26 S2 C23 C43 179.0(4) . . . . ?
C43 C23 C24 C25 -178.4(4) . . . . ?
S2 C23 C24 C25 0.9(4) . . . . ?
C23 C24 C25 C26 -1.2(5) . . . . ?
C23 C24 C25 C27 174.7(3) . . . . ?
C24 C25 C26 S2 0.9(4) . . . . ?
C27 C25 C26 S2 -175.0(3) . . . . ?
C23 S2 C26 C25 -0.4(3) . . . . ?
C26 C25 C27 C28 50.9(4) . . . . ?
C24 C25 C27 C28 -124.5(3) . . . . ?
C26 C25 C27 C40 -131.5(4) . . . . ?
C24 C25 C27 C40 53.1(4) . . . . ?
C40 C27 C28 C29 -1.5(4) . . . . ?
C25 C27 C28 C29 176.2(3) . . . . ?
C27 C28 C29 C30 -0.1(5) . . . . ?
C28 C29 C30 C41 1.3(4) . . . . ?
C28 C29 C30 C31 -179.2(3) . . . . ?
C29 C30 C31 C32 -179.9(3) . . . . ?
C41 C30 C31 C32 -0.4(4) . . . . ?
C30 C31 C32 C33 0.9(5) . . . . ?
C31 C32 C33 C34 179.9(3) . . . . ?
C31 C32 C33 C42 -0.4(4) . . . . ?
C42 C33 C34 C35 0.9(5) . . . . ?
C32 C33 C34 C35 -179.4(3) . . . . ?
C33 C34 C35 C36 -0.2(5) . . . . ?
C34 C35 C36 C37 -0.3(5) . . . . ?
C35 C36 C37 C42 0.2(4) . . . . ?
C35 C36 C37 C38 -179.8(3) . . . . ?
C36 C37 C38 C39 179.3(3) . . . . ?
C42 C37 C38 C39 -0.8(4) . . . . ?
C37 C38 C39 C40 -0.2(4) . . . . ?
C28 C27 C40 C41 2.0(4) . . . . ?
C25 C27 C40 C41 -175.7(3) . . . . ?
C28 C27 C40 C39 -176.7(3) . . . . ?
C25 C27 C40 C39 5.7(4) . . . . ?
C38 C39 C40 C27 -179.9(3) . . . . ?
C38 C39 C40 C41 1.5(4) . . . . ?
C29 C30 C41 C40 -0.9(4) . . . . ?
C31 C30 C41 C40 179.6(3) . . . . ?
C29 C30 C41 C42 178.9(3) . . . . ?
C31 C30 C41 C42 -0.6(4) . . . . ?
C27 C40 C41 C30 -0.8(4) . . . . ?
C39 C40 C41 C30 177.9(2) . . . . ?
C27 C40 C41 C42 179.5(2) . . . . ?
C39 C40 C41 C42 -1.8(4) . . . . ?
C36 C37 C42 C41 -179.7(3) . . . . ?
C38 C37 C42 C41 0.3(4) . . . . ?
C36 C37 C42 C33 0.4(4) . . . . ?
C38 C37 C42 C33 -179.6(3) . . . . ?
C30 C41 C42 C37 -178.8(2) . . . . ?
C40 C41 C42 C37 1.0(4) . . . . ?
C30 C41 C42 C33 1.1(4) . . . . ?
C40 C41 C42 C33 -179.1(2) . . . . ?
C34 C33 C42 C37 -0.9(4) . . . . ?
C32 C33 C42 C37 179.3(2) . . . . ?
C34 C33 C42 C41 179.1(3) . . . . ?
C32 C33 C42 C41 -0.6(4) . . . . ?
C24 C23 C43 C44 132.0(7) . . . . ?
S2 C23 C43 C44 -47.1(8) . . . . ?

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

#==============================================================================
# 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        2-Ethyl-4-(pyren-1-yl)thiophene
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_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_mina221
_database_code_depnum_ccdc_archive 'CCDC 1947304'
loop_
_audit_author_name
_audit_author_address
'Suguru Ito'
;Yokohama National University
Japan
;
_audit_update_record             
;
2019-08-15 deposited with the CCDC.	2019-09-12 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C25 H22 S'
_chemical_formula_moiety         'C25 H22 S'
_chemical_formula_weight         354.51
_chemical_melting_point          326.15-328.15

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   8.77664(13)
_cell_length_b                   9.33669(16)
_cell_length_c                   12.0593(2)
_cell_angle_alpha                93.6123(14)
_cell_angle_beta                 106.3533(14)
_cell_angle_gamma                99.6734(13)
_cell_volume                     928.36(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5943
_cell_measurement_theta_min      4.81
_cell_measurement_theta_max      72.81
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.382
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.110
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376.00
_exptl_absorpt_coefficient_mu    1.558
_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  0.690
_exptl_absorpt_correction_T_max  0.843

#==============================================================================
# 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            9050
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_theta_max         68.227
_diffrn_reflns_theta_min         4.838
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3389
_reflns_number_gt                3066
_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          0.0371
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0939
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3389
_refine_ls_number_parameters     235
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0451P)²+0.1631P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.24
_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)
;
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 0.49578(4) 0.92831(4) 0.34969(3) 0.04178(13) Uani 1 1 d . . . . .
C1 C 0.46075(16) 0.82238(16) 0.21895(12) 0.0369(3) Uani 1 1 d . . . . .
C2 C 0.57759(15) 0.74175(15) 0.22720(12) 0.0345(3) Uani 1 1 d . . . . .
H2 H 0.5794 0.6769 0.1649 0.041 Uiso 1 1 calc R U . . .
C3 C 0.69798(15) 0.76331(15) 0.33844(11) 0.0323(3) Uani 1 1 d . . . . .
C4 C 0.66695(16) 0.86304(15) 0.41285(12) 0.0365(3) Uani 1 1 d . . . . .
H4 H 0.7322 0.8925 0.4900 0.044 Uiso 1 1 calc R U . . .
C5 C 0.84415(15) 0.69604(15) 0.36610(11) 0.0308(3) Uani 1 1 d . . . . .
C6 C 0.99453(16) 0.78438(15) 0.42313(11) 0.0346(3) Uani 1 1 d . . . . .
H6 H 0.9991 0.8821 0.4501 0.042 Uiso 1 1 calc R U . . .
C7 C 1.13694(16) 0.73254(16) 0.44111(12) 0.0366(3) Uani 1 1 d . . . . .
H7 H 1.2358 0.7945 0.4816 0.044 Uiso 1 1 calc R U . . .
C8 C 1.13571(15) 0.58956(15) 0.39992(11) 0.0324(3) Uani 1 1 d . . . . .
C9 C 1.28170(16) 0.53400(17) 0.40820(12) 0.0393(3) Uani 1 1 d . . . . .
H9 H 1.3826 0.5964 0.4422 0.047 Uiso 1 1 calc R U . . .
C10 C 1.27711(17) 0.39557(18) 0.36858(12) 0.0417(3) Uani 1 1 d . . . . .
H10 H 1.3748 0.3634 0.3747 0.050 Uiso 1 1 calc R U . . .
C11 C 1.12677(17) 0.29536(16) 0.31710(12) 0.0366(3) Uani 1 1 d . . . . .
C12 C 1.1181(2) 0.14917(18) 0.27766(13) 0.0461(4) Uani 1 1 d . . . . .
H12 H 1.2142 0.1145 0.2833 0.055 Uiso 1 1 calc R U . . .
C13 C 0.9712(2) 0.05511(18) 0.23069(14) 0.0485(4) Uani 1 1 d . . . . .
H13 H 0.9686 -0.0430 0.2058 0.058 Uiso 1 1 calc R U . . .
C14 C 0.8276(2) 0.10354(17) 0.21980(13) 0.0445(4) Uani 1 1 d . . . . .
H14 H 0.7283 0.0382 0.1876 0.053 Uiso 1 1 calc R U . . .
C15 C 0.82947(17) 0.24888(15) 0.25637(12) 0.0356(3) Uani 1 1 d . . . . .
C16 C 0.68407(16) 0.30354(16) 0.24796(13) 0.0383(3) Uani 1 1 d . . . . .
H16 H 0.5836 0.2394 0.2174 0.046 Uiso 1 1 calc R U . . .
C17 C 0.68751(15) 0.44445(15) 0.28270(12) 0.0349(3) Uani 1 1 d . . . . .
H17 H 0.5893 0.4762 0.2750 0.042 Uiso 1 1 calc R U . . .
C18 C 0.83709(15) 0.54746(14) 0.33114(11) 0.0295(3) Uani 1 1 d . . . . .
C19 C 0.98424(15) 0.49463(14) 0.34580(10) 0.0293(3) Uani 1 1 d . . . . .
C20 C 0.97974(16) 0.34659(15) 0.30606(11) 0.0319(3) Uani 1 1 d . . . . .
C21 C 0.31547(17) 0.82362(19) 0.11703(13) 0.0445(4) Uani 1 1 d . . . . .
H21A H 0.3341 0.7836 0.0460 0.053 Uiso 1 1 calc R U . . .
H21B H 0.3024 0.9250 0.1087 0.053 Uiso 1 1 calc R U . . .
C22 C 0.15992(16) 0.73519(17) 0.12978(12) 0.0392(3) Uani 1 1 d . . . . .
H22A H 0.1730 0.6337 0.1373 0.047 Uiso 1 1 calc R U . . .
H22B H 0.1426 0.7744 0.2016 0.047 Uiso 1 1 calc R U . . .
C23 C 0.01080(17) 0.73645(18) 0.02836(12) 0.0422(3) Uani 1 1 d . . . . .
H23A H -0.0010 0.8379 0.0192 0.051 Uiso 1 1 calc R U . . .
H23B H 0.0260 0.6940 -0.0433 0.051 Uiso 1 1 calc R U . . .
C24 C -0.14258(18) 0.6517(2) 0.04523(13) 0.0473(4) Uani 1 1 d . . . . .
H24A H -0.1333 0.5488 0.0490 0.057 Uiso 1 1 calc R U . . .
H24B H -0.1529 0.6896 0.1199 0.057 Uiso 1 1 calc R U . . .
C25 C -0.2945(2) 0.6601(3) -0.05041(15) 0.0682(6) Uani 1 1 d . . . . .
H25A H -0.3879 0.6039 -0.0345 0.082 Uiso 1 1 calc R U . . .
H25B H -0.3063 0.7614 -0.0535 0.082 Uiso 1 1 calc R U . . .
H25C H -0.2866 0.6205 -0.1245 0.082 Uiso 1 1 calc R U . . .


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

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

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.7118(14) . ?
S1 C1 1.7282(15) . ?
C1 C2 1.3564(19) . ?
C1 C21 1.5035(19) . ?
C2 C3 1.4327(18) . ?
C2 H2 0.9400 . ?
C3 C4 1.3653(19) . ?
C3 C5 1.4858(17) . ?
C4 H4 0.9400 . ?
C5 C6 1.3953(18) . ?
C5 C18 1.4103(19) . ?
C6 C7 1.3811(19) . ?
C6 H6 0.9400 . ?
C7 C8 1.392(2) . ?
C7 H7 0.9400 . ?
C8 C19 1.4217(18) . ?
C8 C9 1.4417(18) . ?
C9 C10 1.340(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.433(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.399(2) . ?
C11 C20 1.4250(18) . ?
C12 C13 1.378(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.384(2) . ?
C13 H13 0.9400 . ?
C14 C15 1.396(2) . ?
C14 H14 0.9400 . ?
C15 C20 1.4186(19) . ?
C15 C16 1.4324(19) . ?
C16 C17 1.348(2) . ?
C16 H16 0.9400 . ?
C17 C18 1.4362(18) . ?
C17 H17 0.9400 . ?
C18 C19 1.4279(17) . ?
C19 C20 1.4245(19) . ?
C21 C22 1.525(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C22 C23 1.5214(19) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C23 C24 1.515(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C24 C25 1.515(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 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
C4 S1 C1 92.37(7) . . ?
C2 C1 C21 128.51(13) . . ?
C2 C1 S1 109.93(10) . . ?
C21 C1 S1 121.54(11) . . ?
C1 C2 C3 114.63(12) . . ?
C1 C2 H2 122.7 . . ?
C3 C2 H2 122.7 . . ?
C4 C3 C2 110.75(12) . . ?
C4 C3 C5 124.43(12) . . ?
C2 C3 C5 124.63(12) . . ?
C3 C4 S1 112.31(10) . . ?
C3 C4 H4 123.8 . . ?
S1 C4 H4 123.8 . . ?
C6 C5 C18 118.83(12) . . ?
C6 C5 C3 118.95(12) . . ?
C18 C5 C3 122.13(11) . . ?
C7 C6 C5 121.98(13) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C8 120.75(12) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C19 118.73(12) . . ?
C7 C8 C9 122.80(12) . . ?
C19 C8 C9 118.46(13) . . ?
C10 C9 C8 121.60(13) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 121.51(13) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C12 C11 C20 118.58(14) . . ?
C12 C11 C10 122.83(13) . . ?
C20 C11 C10 118.59(13) . . ?
C13 C12 C11 121.22(14) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 120.70(15) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C15 120.36(15) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C20 119.58(13) . . ?
C14 C15 C16 122.34(13) . . ?
C20 C15 C16 118.07(13) . . ?
C17 C16 C15 121.75(13) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C18 121.82(12) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C5 C18 C19 119.27(11) . . ?
C5 C18 C17 123.00(12) . . ?
C19 C18 C17 117.73(12) . . ?
C8 C19 C20 119.77(12) . . ?
C8 C19 C18 120.16(12) . . ?
C20 C19 C18 120.08(12) . . ?
C15 C20 C19 120.43(12) . . ?
C15 C20 C11 119.54(13) . . ?
C19 C20 C11 120.02(12) . . ?
C1 C21 C22 112.76(12) . . ?
C1 C21 H21A 109.0 . . ?
C22 C21 H21A 109.0 . . ?
C1 C21 H21B 109.0 . . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C23 C22 C21 113.71(12) . . ?
C23 C22 H22A 108.8 . . ?
C21 C22 H22A 108.8 . . ?
C23 C22 H22B 108.8 . . ?
C21 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
C24 C23 C22 112.50(12) . . ?
C24 C23 H23A 109.1 . . ?
C22 C23 H23A 109.1 . . ?
C24 C23 H23B 109.1 . . ?
C22 C23 H23B 109.1 . . ?
H23A C23 H23B 107.8 . . ?
C25 C24 C23 113.60(14) . . ?
C25 C24 H24A 108.8 . . ?
C23 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C23 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C4 S1 C1 C2 0.23(11) . . . . ?
C4 S1 C1 C21 178.51(12) . . . . ?
C21 C1 C2 C3 -178.26(13) . . . . ?
S1 C1 C2 C3 -0.12(15) . . . . ?
C1 C2 C3 C4 -0.08(17) . . . . ?
C1 C2 C3 C5 -175.28(12) . . . . ?
C2 C3 C4 S1 0.25(15) . . . . ?
C5 C3 C4 S1 175.47(10) . . . . ?
C1 S1 C4 C3 -0.28(11) . . . . ?
C4 C3 C5 C6 -42.69(19) . . . . ?
C2 C3 C5 C6 131.86(14) . . . . ?
C4 C3 C5 C18 140.76(14) . . . . ?
C2 C3 C5 C18 -44.68(19) . . . . ?
C18 C5 C6 C7 3.3(2) . . . . ?
C3 C5 C6 C7 -173.38(12) . . . . ?
C5 C6 C7 C8 1.6(2) . . . . ?
C6 C7 C8 C19 -4.20(19) . . . . ?
C6 C7 C8 C9 174.86(12) . . . . ?
C7 C8 C9 C10 179.52(13) . . . . ?
C19 C8 C9 C10 -1.4(2) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
C9 C10 C11 C12 -178.31(14) . . . . ?
C9 C10 C11 C20 1.4(2) . . . . ?
C20 C11 C12 C13 -1.0(2) . . . . ?
C10 C11 C12 C13 178.68(13) . . . . ?
C11 C12 C13 C14 0.9(2) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 C20 -0.7(2) . . . . ?
C13 C14 C15 C16 -179.33(13) . . . . ?
C14 C15 C16 C17 -179.44(14) . . . . ?
C20 C15 C16 C17 1.9(2) . . . . ?
C15 C16 C17 C18 -0.6(2) . . . . ?
C6 C5 C18 C19 -5.39(18) . . . . ?
C3 C5 C18 C19 171.15(11) . . . . ?
C6 C5 C18 C17 173.50(12) . . . . ?
C3 C5 C18 C17 -9.96(19) . . . . ?
C16 C17 C18 C5 178.75(13) . . . . ?
C16 C17 C18 C19 -2.3(2) . . . . ?
C7 C8 C19 C20 -178.14(12) . . . . ?
C9 C8 C19 C20 2.76(18) . . . . ?
C7 C8 C19 C18 1.95(18) . . . . ?
C9 C8 C19 C18 -177.15(11) . . . . ?
C5 C18 C19 C8 2.84(18) . . . . ?
C17 C18 C19 C8 -176.11(11) . . . . ?
C5 C18 C19 C20 -177.07(11) . . . . ?
C17 C18 C19 C20 3.98(18) . . . . ?
C14 C15 C20 C19 -178.88(12) . . . . ?
C16 C15 C20 C19 -0.18(19) . . . . ?
C14 C15 C20 C11 0.51(19) . . . . ?
C16 C15 C20 C11 179.21(12) . . . . ?
C8 C19 C20 C15 177.32(11) . . . . ?
C18 C19 C20 C15 -2.78(19) . . . . ?
C8 C19 C20 C11 -2.07(18) . . . . ?
C18 C19 C20 C11 177.84(11) . . . . ?
C12 C11 C20 C15 0.33(19) . . . . ?
C10 C11 C20 C15 -179.39(12) . . . . ?
C12 C11 C20 C19 179.72(12) . . . . ?
C10 C11 C20 C19 0.00(19) . . . . ?
C2 C1 C21 C22 101.17(17) . . . . ?
S1 C1 C21 C22 -76.77(16) . . . . ?
C1 C21 C22 C23 179.25(13) . . . . ?
C21 C22 C23 C24 -178.20(13) . . . . ?
C22 C23 C24 C25 175.89(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        2-Pentyl-4-(pyren-1-yl)thiophene
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_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_mina245_1
_database_code_depnum_ccdc_archive 'CCDC 1947303'
loop_
_audit_author_name
_audit_author_address
'Suguru Ito'
;Yokohama National University
Japan
;
_audit_update_record             
;
2019-08-15 deposited with the CCDC.	2019-09-12 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C23 H18 S'
_chemical_formula_moiety         'C23 H18 S'
_chemical_formula_weight         326.46
_chemical_melting_point          340.15-342.15
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.65747(11)
_cell_length_b                   14.0292(2)
_cell_length_c                   15.4998(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1665.12(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5178
_cell_measurement_theta_min      4.25
_cell_measurement_theta_max      72.73
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.128
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688.00
_exptl_absorpt_coefficient_mu    1.693
_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  0.638
_exptl_absorpt_correction_T_max  0.805

#==============================================================================
# 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            7128
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_theta_max         68.230
_diffrn_reflns_theta_min         4.251
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2959
_reflns_number_gt                2793
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_max     0.932
_reflns_Friedel_fraction_full    0.937

#==============================================================================
# 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          0.0369
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0926
_refine_ls_wR_factor_gt          0.0910
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2959
_refine_ls_number_parameters     217
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0481P)²+0.1412P] 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         -0.22
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1069 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(14)

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)
;
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 0.76411(9) 0.87120(4) 0.57464(5) 0.03519(19) Uani 1 1 d . . . . .
C1 C 0.9189(3) 0.81966(19) 0.64056(17) 0.0303(6) Uani 1 1 d . . . . .
C2 C 0.8781(3) 0.72654(18) 0.65681(16) 0.0278(6) Uani 1 1 d . . . . .
H2 H 0.9478 0.6862 0.6909 0.033 Uiso 1 1 calc R U . . .
C3 C 0.7190(3) 0.69652(17) 0.61695(16) 0.0270(5) Uani 1 1 d . . . . .
C4 C 0.6438(3) 0.76803(17) 0.57038(18) 0.0322(6) Uani 1 1 d . . . . .
H4 H 0.5386 0.7616 0.5396 0.039 Uiso 1 1 calc R U . . .
C5 C 0.6361(3) 0.60175(17) 0.62817(16) 0.0266(6) Uani 1 1 d . . . . .
C6 C 0.4606(3) 0.59890(19) 0.65392(18) 0.0310(6) Uani 1 1 d . . . . .
H6 H 0.3991 0.6563 0.6611 0.037 Uiso 1 1 calc R U . . .
C7 C 0.3763(3) 0.51358(19) 0.66894(17) 0.0320(6) Uani 1 1 d . . . . .
H7 H 0.2589 0.5140 0.6866 0.038 Uiso 1 1 calc R U . . .
C8 C 0.4625(3) 0.4267(2) 0.65832(16) 0.0291(6) Uani 1 1 d . . . . .
C9 C 0.3805(4) 0.33710(19) 0.67720(18) 0.0336(6) Uani 1 1 d . . . . .
H9 H 0.2645 0.3364 0.6971 0.040 Uiso 1 1 calc R U . . .
C10 C 0.4656(4) 0.2544(2) 0.66709(17) 0.0343(6) Uani 1 1 d . . . . .
H10 H 0.4081 0.1971 0.6804 0.041 Uiso 1 1 calc R U . . .
C11 C 0.6423(4) 0.25117(19) 0.63649(17) 0.0306(6) Uani 1 1 d . . . . .
C12 C 0.7328(4) 0.16550(19) 0.62498(18) 0.0368(6) Uani 1 1 d . . . . .
H12 H 0.6780 0.1074 0.6384 0.044 Uiso 1 1 calc R U . . .
C13 C 0.9027(4) 0.16555(19) 0.59398(19) 0.0385(7) Uani 1 1 d . . . . .
H13 H 0.9609 0.1073 0.5855 0.046 Uiso 1 1 calc R U . . .
C14 C 0.9878(4) 0.25025(18) 0.57535(17) 0.0336(6) Uani 1 1 d . . . . .
H14 H 1.1031 0.2488 0.5546 0.040 Uiso 1 1 calc R U . . .
C15 C 0.9036(3) 0.33805(18) 0.58722(16) 0.0276(5) Uani 1 1 d . . . . .
C16 C 0.9872(3) 0.42753(18) 0.57043(17) 0.0282(5) Uani 1 1 d . . . . .
H16 H 1.1025 0.4280 0.5496 0.034 Uiso 1 1 calc R U . . .
C17 C 0.9042(3) 0.51113(17) 0.58391(16) 0.0271(5) Uani 1 1 d . . . . .
H17 H 0.9640 0.5684 0.5730 0.033 Uiso 1 1 calc R U . . .
C18 C 0.7263(3) 0.51528(17) 0.61461(15) 0.0247(5) Uani 1 1 d . . . . .
C19 C 0.6394(3) 0.42704(18) 0.62980(15) 0.0253(5) Uani 1 1 d . . . . .
C20 C 0.7282(3) 0.33858(18) 0.61737(15) 0.0264(5) Uani 1 1 d . . . . .
C21 C 1.0687(4) 0.8767(2) 0.67522(17) 0.0344(6) Uani 1 1 d . . . . .
H21A H 1.1437 0.8346 0.7094 0.041 Uiso 1 1 calc R U . . .
H21B H 1.0227 0.9258 0.7140 0.041 Uiso 1 1 calc R U . . .
C22 C 1.1796(3) 0.92479(19) 0.60656(17) 0.0318(6) Uani 1 1 d . . . . .
H22A H 1.2406 0.8758 0.5730 0.038 Uiso 1 1 calc R U . . .
H22B H 1.1032 0.9600 0.5671 0.038 Uiso 1 1 calc R U . . .
C23 C 1.3126(4) 0.9927(2) 0.6445(2) 0.0479(8) Uani 1 1 d . . . . .
H23A H 1.3799 1.0215 0.5983 0.058 Uiso 1 1 calc R U . . .
H23B H 1.2529 1.0422 0.6767 0.058 Uiso 1 1 calc R U . . .
H23C H 1.3902 0.9580 0.6827 0.058 Uiso 1 1 calc R U . . .


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

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

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.717(3) . ?
S1 C1 1.724(3) . ?
C1 C2 1.367(3) . ?
C1 C21 1.499(4) . ?
C2 C3 1.430(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.364(3) . ?
C3 C5 1.483(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.402(4) . ?
C5 C18 1.412(3) . ?
C6 C7 1.380(4) . ?
C6 H6 0.9400 . ?
C7 C8 1.396(4) . ?
C7 H7 0.9400 . ?
C8 C19 1.425(3) . ?
C8 C9 1.435(3) . ?
C9 C10 1.340(4) . ?
C9 H9 0.9400 . ?
C10 C11 1.434(4) . ?
C10 H10 0.9400 . ?
C11 C12 1.399(4) . ?
C11 C20 1.423(3) . ?
C12 C13 1.387(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.386(4) . ?
C13 H13 0.9400 . ?
C14 C15 1.402(3) . ?
C14 H14 0.9400 . ?
C15 C20 1.423(4) . ?
C15 C16 1.433(3) . ?
C16 C17 1.350(3) . ?
C16 H16 0.9400 . ?
C17 C18 1.444(3) . ?
C17 H17 0.9400 . ?
C18 C19 1.425(3) . ?
C19 C20 1.428(3) . ?
C21 C22 1.519(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C22 C23 1.513(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 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
C4 S1 C1 92.20(12) . . ?
C2 C1 C21 128.3(3) . . ?
C2 C1 S1 110.7(2) . . ?
C21 C1 S1 121.0(2) . . ?
C1 C2 C3 113.4(2) . . ?
C1 C2 H2 123.3 . . ?
C3 C2 H2 123.3 . . ?
C4 C3 C2 111.8(2) . . ?
C4 C3 C5 122.7(2) . . ?
C2 C3 C5 125.3(2) . . ?
C3 C4 S1 111.9(2) . . ?
C3 C4 H4 124.0 . . ?
S1 C4 H4 124.0 . . ?
C6 C5 C18 119.1(2) . . ?
C6 C5 C3 118.0(2) . . ?
C18 C5 C3 122.9(2) . . ?
C7 C6 C5 121.4(2) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 121.1(2) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C19 118.9(2) . . ?
C7 C8 C9 122.3(2) . . ?
C19 C8 C9 118.8(2) . . ?
C10 C9 C8 121.4(2) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 121.7(2) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C12 C11 C20 119.0(3) . . ?
C12 C11 C10 122.5(3) . . ?
C20 C11 C10 118.5(3) . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C20 118.8(2) . . ?
C14 C15 C16 122.7(2) . . ?
C20 C15 C16 118.5(2) . . ?
C17 C16 C15 121.5(2) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 122.0(2) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 H17 119.0 . . ?
C5 C18 C19 119.6(2) . . ?
C5 C18 C17 123.0(2) . . ?
C19 C18 C17 117.4(2) . . ?
C8 C19 C18 119.9(2) . . ?
C8 C19 C20 119.4(2) . . ?
C18 C19 C20 120.7(2) . . ?
C15 C20 C11 120.0(2) . . ?
C15 C20 C19 119.9(2) . . ?
C11 C20 C19 120.1(2) . . ?
C1 C21 C22 114.5(2) . . ?
C1 C21 H21A 108.6 . . ?
C22 C21 H21A 108.6 . . ?
C1 C21 H21B 108.6 . . ?
C22 C21 H21B 108.6 . . ?
H21A C21 H21B 107.6 . . ?
C23 C22 C21 112.6(2) . . ?
C23 C22 H22A 109.1 . . ?
C21 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
C21 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C4 S1 C1 C2 0.8(2) . . . . ?
C4 S1 C1 C21 -176.7(2) . . . . ?
C21 C1 C2 C3 176.3(2) . . . . ?
S1 C1 C2 C3 -0.9(3) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C1 C2 C3 C5 -175.5(2) . . . . ?
C2 C3 C4 S1 -0.1(3) . . . . ?
C5 C3 C4 S1 176.3(2) . . . . ?
C1 S1 C4 C3 -0.4(2) . . . . ?
C4 C3 C5 C6 -49.1(4) . . . . ?
C2 C3 C5 C6 126.7(3) . . . . ?
C4 C3 C5 C18 131.3(3) . . . . ?
C2 C3 C5 C18 -52.9(4) . . . . ?
C18 C5 C6 C7 2.1(4) . . . . ?
C3 C5 C6 C7 -177.5(2) . . . . ?
C5 C6 C7 C8 -0.6(4) . . . . ?
C6 C7 C8 C19 -1.2(4) . . . . ?
C6 C7 C8 C9 177.1(3) . . . . ?
C7 C8 C9 C10 -179.6(3) . . . . ?
C19 C8 C9 C10 -1.2(4) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C9 C10 C11 C12 -179.5(3) . . . . ?
C9 C10 C11 C20 0.6(4) . . . . ?
C20 C11 C12 C13 -1.1(4) . . . . ?
C10 C11 C12 C13 179.0(2) . . . . ?
C11 C12 C13 C14 1.3(4) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C20 -1.0(4) . . . . ?
C13 C14 C15 C16 178.8(3) . . . . ?
C14 C15 C16 C17 -178.8(3) . . . . ?
C20 C15 C16 C17 1.1(4) . . . . ?
C15 C16 C17 C18 -1.0(4) . . . . ?
C6 C5 C18 C19 -1.9(4) . . . . ?
C3 C5 C18 C19 177.7(2) . . . . ?
C6 C5 C18 C17 176.8(2) . . . . ?
C3 C5 C18 C17 -3.6(4) . . . . ?
C16 C17 C18 C5 -179.2(2) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
C7 C8 C19 C18 1.4(4) . . . . ?
C9 C8 C19 C18 -177.0(2) . . . . ?
C7 C8 C19 C20 -179.0(2) . . . . ?
C9 C8 C19 C20 2.5(4) . . . . ?
C5 C18 C19 C8 0.1(4) . . . . ?
C17 C18 C19 C8 -178.6(2) . . . . ?
C5 C18 C19 C20 -179.4(2) . . . . ?
C17 C18 C19 C20 1.8(3) . . . . ?
C14 C15 C20 C11 1.2(4) . . . . ?
C16 C15 C20 C11 -178.6(2) . . . . ?
C14 C15 C20 C19 -179.9(2) . . . . ?
C16 C15 C20 C19 0.3(4) . . . . ?
C12 C11 C20 C15 -0.1(4) . . . . ?
C10 C11 C20 C15 179.7(2) . . . . ?
C12 C11 C20 C19 -179.1(2) . . . . ?
C10 C11 C20 C19 0.8(4) . . . . ?
C8 C19 C20 C15 178.7(2) . . . . ?
C18 C19 C20 C15 -1.8(4) . . . . ?
C8 C19 C20 C11 -2.3(4) . . . . ?
C18 C19 C20 C11 177.2(2) . . . . ?
C2 C1 C21 C22 126.5(3) . . . . ?
S1 C1 C21 C22 -56.6(3) . . . . ?
C1 C21 C22 C23 171.7(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        2-Propyl-4-(pyren-1-yl)thiophene
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_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_mina204_2
_database_code_depnum_ccdc_archive 'CCDC 1947305'
loop_
_audit_author_name
_audit_author_address
'Suguru Ito'
;Yokohama National University
Japan
;
_audit_update_record             
;
2019-08-15 deposited with the CCDC.	2019-09-12 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C26 H24 S'
_chemical_formula_moiety         'C26 H24 S'
_chemical_formula_weight         368.54
_chemical_melting_point          328.15-330.15

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   8.71844(12)
_cell_length_b                   10.13255(17)
_cell_length_c                   22.2883(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.7546(13)
_cell_angle_gamma                90.0000
_cell_volume                     1968.03(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7922
_cell_measurement_theta_min      4.79
_cell_measurement_theta_max      74.87
_cell_measurement_temperature    223
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.518
_exptl_crystal_size_mid          0.344
_exptl_crystal_size_min          0.127
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784.00
_exptl_absorpt_coefficient_mu    1.488
_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  0.469
_exptl_absorpt_correction_T_max  0.828

#==============================================================================
# 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            13816
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_theta_max         68.236
_diffrn_reflns_theta_min         3.969
_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       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3608
_reflns_number_gt                3158
_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          0.0434
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1087
_refine_ls_wR_factor_gt          0.1052
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3608
_refine_ls_number_parameters     244
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0502P)²+0.4835P] 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         0.26
_refine_diff_density_min         -0.29
_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)
;
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 1.25060(4) 1.09815(4) 0.12775(2) 0.04547(15) Uani 1 1 d . . . . .
C1 C 1.12146(19) 1.12563(16) 0.06875(7) 0.0415(4) Uani 1 1 d . . . . .
C2 C 0.99421(18) 1.05092(16) 0.07534(7) 0.0412(4) Uani 1 1 d . . . . .
H2 H 0.9099 1.0535 0.0480 0.049 Uiso 1 1 calc R U . . .
C3 C 0.99867(18) 0.96792(15) 0.12718(6) 0.0386(3) Uani 1 1 d . . . . .
C4 C 1.13218(18) 0.98475(16) 0.15969(7) 0.0432(4) Uani 1 1 d . . . . .
H4 H 1.1565 0.9394 0.1955 0.052 Uiso 1 1 calc R U . . .
C5 C 0.87080(17) 0.87838(15) 0.14197(6) 0.0369(3) Uani 1 1 d . . . . .
C6 C 0.72088(18) 0.92928(17) 0.14095(7) 0.0437(4) Uani 1 1 d . . . . .
H6 H 0.7055 1.0190 0.1318 0.052 Uiso 1 1 calc R U . . .
C7 C 0.59583(18) 0.85178(18) 0.15294(8) 0.0460(4) Uani 1 1 d . . . . .
H7 H 0.4973 0.8896 0.1521 0.055 Uiso 1 1 calc R U . . .
C8 C 0.61289(17) 0.71812(17) 0.16626(7) 0.0399(4) Uani 1 1 d . . . . .
C9 C 0.48494(18) 0.63341(19) 0.17839(8) 0.0489(4) Uani 1 1 d . . . . .
H9 H 0.3856 0.6695 0.1781 0.059 Uiso 1 1 calc R U . . .
C10 C 0.50353(18) 0.50480(19) 0.19012(8) 0.0499(4) Uani 1 1 d . . . . .
H10 H 0.4172 0.4528 0.1980 0.060 Uiso 1 1 calc R U . . .
C11 C 0.65232(18) 0.44474(17) 0.19087(6) 0.0418(4) Uani 1 1 d . . . . .
C12 C 0.6744(2) 0.31045(18) 0.20211(7) 0.0485(4) Uani 1 1 d . . . . .
H12 H 0.5893 0.2564 0.2092 0.058 Uiso 1 1 calc R U . . .
C13 C 0.8193(2) 0.25592(17) 0.20288(7) 0.0494(4) Uani 1 1 d . . . . .
H13 H 0.8321 0.1655 0.2111 0.059 Uiso 1 1 calc R U . . .
C14 C 0.9456(2) 0.33299(16) 0.19163(7) 0.0452(4) Uani 1 1 d . . . . .
H14 H 1.0437 0.2944 0.1922 0.054 Uiso 1 1 calc R U . . .
C15 C 0.92998(17) 0.46747(15) 0.17945(6) 0.0378(3) Uani 1 1 d . . . . .
C16 C 1.05690(17) 0.55040(16) 0.16553(7) 0.0408(4) Uani 1 1 d . . . . .
H16 H 1.1556 0.5133 0.1647 0.049 Uiso 1 1 calc R U . . .
C17 C 1.03943(16) 0.67981(16) 0.15354(7) 0.0383(3) Uani 1 1 d . . . . .
H17 H 1.1260 0.7301 0.1441 0.046 Uiso 1 1 calc R U . . .
C18 C 0.89214(16) 0.74339(15) 0.15478(6) 0.0337(3) Uani 1 1 d . . . . .
C19 C 0.76271(15) 0.66283(15) 0.16716(6) 0.0336(3) Uani 1 1 d . . . . .
C20 C 0.78160(16) 0.52532(15) 0.17922(6) 0.0351(3) Uani 1 1 d . . . . .
C21 C 1.1570(2) 1.22000(17) 0.01884(7) 0.0486(4) Uani 1 1 d . . . . .
H21A H 1.0681 1.2248 -0.0090 0.058 Uiso 1 1 calc R U . . .
H21B H 1.2435 1.1852 -0.0034 0.058 Uiso 1 1 calc R U . . .
C22 C 1.1963(2) 1.35810(17) 0.04047(7) 0.0472(4) Uani 1 1 d . . . . .
H22A H 1.2832 1.3527 0.0693 0.057 Uiso 1 1 calc R U . . .
H22B H 1.1086 1.3935 0.0617 0.057 Uiso 1 1 calc R U . . .
C23 C 1.2372(2) 1.45434(17) -0.00922(7) 0.0471(4) Uani 1 1 d . . . . .
H23A H 1.3227 1.4182 -0.0316 0.057 Uiso 1 1 calc R U . . .
H23B H 1.1490 1.4639 -0.0372 0.057 Uiso 1 1 calc R U . . .
C24 C 1.2819(2) 1.58897(17) 0.01525(8) 0.0499(4) Uani 1 1 d . . . . .
H24A H 1.3667 1.5776 0.0447 0.060 Uiso 1 1 calc R U . . .
H24B H 1.1947 1.6251 0.0365 0.060 Uiso 1 1 calc R U . . .
C25 C 1.3303(2) 1.68920(18) -0.03108(8) 0.0531(4) Uani 1 1 d . . . . .
H25A H 1.4143 1.6524 -0.0540 0.064 Uiso 1 1 calc R U . . .
H25B H 1.2438 1.7062 -0.0591 0.064 Uiso 1 1 calc R U . . .
C26 C 1.3822(3) 1.8184(2) -0.00277(10) 0.0671(6) Uani 1 1 d . . . . .
H26A H 1.4118 1.8792 -0.0339 0.080 Uiso 1 1 calc R U . . .
H26B H 1.2987 1.8562 0.0193 0.080 Uiso 1 1 calc R U . . .
H26C H 1.4691 1.8024 0.0244 0.080 Uiso 1 1 calc R U . . .


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

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

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.7141(17) . ?
S1 C1 1.7273(16) . ?
C1 C2 1.355(2) . ?
C1 C21 1.506(2) . ?
C2 C3 1.429(2) . ?
C2 H2 0.9400 . ?
C3 C4 1.363(2) . ?
C3 C5 1.482(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.405(2) . ?
C5 C18 1.408(2) . ?
C6 C7 1.376(2) . ?
C6 H6 0.9400 . ?
C7 C8 1.393(2) . ?
C7 H7 0.9400 . ?
C8 C19 1.4209(19) . ?
C8 C9 1.440(2) . ?
C9 C10 1.338(3) . ?
C9 H9 0.9400 . ?
C10 C11 1.432(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.396(2) . ?
C11 C20 1.422(2) . ?
C12 C13 1.378(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.379(2) . ?
C13 H13 0.9400 . ?
C14 C15 1.395(2) . ?
C14 H14 0.9400 . ?
C15 C20 1.420(2) . ?
C15 C16 1.431(2) . ?
C16 C17 1.346(2) . ?
C16 H16 0.9400 . ?
C17 C18 1.4377(19) . ?
C17 H17 0.9400 . ?
C18 C19 1.426(2) . ?
C19 C20 1.428(2) . ?
C21 C22 1.516(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C22 C23 1.526(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C23 C24 1.516(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C24 C25 1.517(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C25 C26 1.516(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 H26C 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
C4 S1 C1 92.14(8) . . ?
C2 C1 C21 128.49(15) . . ?
C2 C1 S1 110.14(12) . . ?
C21 C1 S1 121.37(13) . . ?
C1 C2 C3 114.48(14) . . ?
C1 C2 H2 122.8 . . ?
C3 C2 H2 122.8 . . ?
C4 C3 C2 110.98(14) . . ?
C4 C3 C5 126.46(14) . . ?
C2 C3 C5 122.56(14) . . ?
C3 C4 S1 112.25(12) . . ?
C3 C4 H4 123.9 . . ?
S1 C4 H4 123.9 . . ?
C6 C5 C18 118.48(14) . . ?
C6 C5 C3 118.52(14) . . ?
C18 C5 C3 122.95(13) . . ?
C7 C6 C5 121.98(16) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C8 121.05(14) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C7 C8 C19 118.57(14) . . ?
C7 C8 C9 122.76(14) . . ?
C19 C8 C9 118.66(15) . . ?
C10 C9 C8 121.83(15) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C9 C10 C11 121.35(15) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C20 119.11(15) . . ?
C12 C11 C10 122.43(15) . . ?
C20 C11 C10 118.46(15) . . ?
C13 C12 C11 120.97(16) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C12 C13 C14 120.48(16) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C15 120.95(15) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C20 119.18(14) . . ?
C14 C15 C16 122.95(14) . . ?
C20 C15 C16 117.85(14) . . ?
C17 C16 C15 122.11(14) . . ?
C17 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
C16 C17 C18 121.90(14) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C5 C18 C19 119.64(13) . . ?
C5 C18 C17 122.94(14) . . ?
C19 C18 C17 117.36(13) . . ?
C8 C19 C18 120.26(14) . . ?
C8 C19 C20 119.22(13) . . ?
C18 C19 C20 120.50(12) . . ?
C15 C20 C11 119.30(14) . . ?
C15 C20 C19 120.22(13) . . ?
C11 C20 C19 120.48(13) . . ?
C1 C21 C22 113.62(13) . . ?
C1 C21 H21A 108.8 . . ?
C22 C21 H21A 108.8 . . ?
C1 C21 H21B 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
C21 C22 C23 114.51(14) . . ?
C21 C22 H22A 108.6 . . ?
C23 C22 H22A 108.6 . . ?
C21 C22 H22B 108.6 . . ?
C23 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C24 C23 C22 112.17(14) . . ?
C24 C23 H23A 109.2 . . ?
C22 C23 H23A 109.2 . . ?
C24 C23 H23B 109.2 . . ?
C22 C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C23 C24 C25 115.55(14) . . ?
C23 C24 H24A 108.4 . . ?
C25 C24 H24A 108.4 . . ?
C23 C24 H24B 108.4 . . ?
C25 C24 H24B 108.4 . . ?
H24A C24 H24B 107.5 . . ?
C26 C25 C24 112.34(16) . . ?
C26 C25 H25A 109.1 . . ?
C24 C25 H25A 109.1 . . ?
C26 C25 H25B 109.1 . . ?
C24 C25 H25B 109.1 . . ?
H25A C25 H25B 107.9 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
C4 S1 C1 C2 0.82(12) . . . . ?
C4 S1 C1 C21 -178.47(13) . . . . ?
C21 C1 C2 C3 178.00(15) . . . . ?
S1 C1 C2 C3 -1.23(17) . . . . ?
C1 C2 C3 C4 1.1(2) . . . . ?
C1 C2 C3 C5 -179.65(13) . . . . ?
C2 C3 C4 S1 -0.42(17) . . . . ?
C5 C3 C4 S1 -179.64(12) . . . . ?
C1 S1 C4 C3 -0.22(13) . . . . ?
C4 C3 C5 C6 130.41(17) . . . . ?
C2 C3 C5 C6 -48.7(2) . . . . ?
C4 C3 C5 C18 -52.1(2) . . . . ?
C2 C3 C5 C18 128.79(16) . . . . ?
C18 C5 C6 C7 1.0(2) . . . . ?
C3 C5 C6 C7 178.65(14) . . . . ?
C5 C6 C7 C8 -0.5(2) . . . . ?
C6 C7 C8 C19 -0.1(2) . . . . ?
C6 C7 C8 C9 -179.28(15) . . . . ?
C7 C8 C9 C10 178.88(16) . . . . ?
C19 C8 C9 C10 -0.3(2) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 -179.02(16) . . . . ?
C9 C10 C11 C20 0.4(2) . . . . ?
C20 C11 C12 C13 1.0(2) . . . . ?
C10 C11 C12 C13 -179.58(15) . . . . ?
C11 C12 C13 C14 -1.0(2) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
C13 C14 C15 C20 0.5(2) . . . . ?
C13 C14 C15 C16 -177.84(14) . . . . ?
C14 C15 C16 C17 179.58(15) . . . . ?
C20 C15 C16 C17 1.2(2) . . . . ?
C15 C16 C17 C18 0.9(2) . . . . ?
C6 C5 C18 C19 -0.9(2) . . . . ?
C3 C5 C18 C19 -178.44(12) . . . . ?
C6 C5 C18 C17 176.30(13) . . . . ?
C3 C5 C18 C17 -1.2(2) . . . . ?
C16 C17 C18 C5 -179.51(14) . . . . ?
C16 C17 C18 C19 -2.2(2) . . . . ?
C7 C8 C19 C18 0.2(2) . . . . ?
C9 C8 C19 C18 179.38(13) . . . . ?
C7 C8 C19 C20 -178.40(13) . . . . ?
C9 C8 C19 C20 0.8(2) . . . . ?
C5 C18 C19 C8 0.4(2) . . . . ?
C17 C18 C19 C8 -177.02(13) . . . . ?
C5 C18 C19 C20 178.90(12) . . . . ?
C17 C18 C19 C20 1.52(19) . . . . ?
C14 C15 C20 C11 -0.5(2) . . . . ?
C16 C15 C20 C11 177.91(12) . . . . ?
C14 C15 C20 C19 179.70(13) . . . . ?
C16 C15 C20 C19 -1.8(2) . . . . ?
C12 C11 C20 C15 -0.2(2) . . . . ?
C10 C11 C20 C15 -179.67(13) . . . . ?
C12 C11 C20 C19 179.57(13) . . . . ?
C10 C11 C20 C19 0.1(2) . . . . ?
C8 C19 C20 C15 179.04(13) . . . . ?
C18 C19 C20 C15 0.5(2) . . . . ?
C8 C19 C20 C11 -0.7(2) . . . . ?
C18 C19 C20 C11 -179.27(12) . . . . ?
C2 C1 C21 C22 124.87(18) . . . . ?
S1 C1 C21 C22 -55.98(19) . . . . ?
C1 C21 C22 C23 178.33(15) . . . . ?
C21 C22 C23 C24 -177.59(15) . . . . ?
C22 C23 C24 C25 177.76(15) . . . . ?
C23 C24 C25 C26 -176.59(16) . . . . ?

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

#==============================================================================
# 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        2-Hexyl-4-(pyren-1-yl)thiophene
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_exptl_crystal_preparation       Luminescent
