# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_lucia5molt
_database_code_depnum_ccdc_archive 'CCDC 1509231'
_audit_update_record             
;
2016-11-25 deposited with the CCDC.
2017-01-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_lucia5molt          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.956 Note
RESPONSE: Alert B due to 1) the completeness is not 100%, some of the reflections have been omitted as they are incorrect , probably due to the disorder  which may screw the intensities. 2) The isotropic refiniment which is also because the structure is disordered which some of the atoms can't refine stably with anisotropic refinement.
;
# Added during the CSD deposition process: Friday 25 November 2016 06:34 AM
# end Validation Reply Form

_audit_creation_date             2015-07-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        (E)-1,2-di(thiophen-2-yl)ethene
_chemical_formula_moiety         'C10 H8 S2'
_chemical_formula_sum            'C10 H8 S2'
_chemical_formula_weight         192.28
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.81321(19)
_cell_length_b                   7.5432(3)
_cell_length_c                   10.2777(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.249(3)
_cell_angle_gamma                90
_cell_volume                     449.95(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1656
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      29.2570
_cell_measurement_theta_min      4.4170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.526
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless

_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             200
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0232

_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2262

_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         3.972
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -42.00   46.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0886  -57.0000  -90.0000 88

#__ type_ start__ end____ width___ exp.time_
  2 omega    1.00   96.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0886   57.0000   60.0000 95

#__ type_ start__ end____ width___ exp.time_
  3 omega  -17.00   81.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.0886   77.0000 -180.0000 98
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0075967000
_diffrn_orient_matrix_UB_12      0.0372046000
_diffrn_orient_matrix_UB_13      -0.0634667000
_diffrn_orient_matrix_UB_21      0.0516411000
_diffrn_orient_matrix_UB_22      0.0791607000
_diffrn_orient_matrix_UB_23      0.0247572000
_diffrn_orient_matrix_UB_31      0.1105337000
_diffrn_orient_matrix_UB_32      -0.0345020000
_diffrn_orient_matrix_UB_33      -0.0116379000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                773
_reflns_number_total             848
_reflns_odcompleteness_completeness 99.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     57
_refine_ls_number_reflns         848
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0510P)²+0.4446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0930
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C2-C1 \\sim C3-C2 \\sim C4-C3
 with sigma of 0.02
 S1A-C1A \\sim S1A-C3
 with sigma of 0.02
 S1-C1 \\sim S1-C4
 with sigma of 0.02
 C2A-C1A \\sim C4-C2A \\sim C4-C3
 with sigma of 0.02
 C5A-C1A \\sim C5-C1
 with sigma of 0.02
3. Restrained planarity
 C1A, S1A, C4, C2A, C3
 with sigma of 0.1
4. Others
 Fixed Sof: S1(0.9) S1A(0.1) C1(0.9) C1A(0.1) C2(0.9) H2(0.9) C2A(0.1)
 H2A(0.1) H3B(0.1) H3A(0.9) H4B(0.1) H4A(0.9) C5(0.92) H5(0.92) C5A(0.08)
 H5A(0.08)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C2A(H2A), C3(H3B), C4(H4B), C5(H5), C5A(H5A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.39149(12) 0.63481(9) 0.36053(8) 0.0175(2) Uiso 0.9 1 d D . P A 1
S1A S 0.0827(15) 0.4672(11) 0.2227(8) 0.023(3) Uiso 0.1 1 d D . P A 2
C1 C 0.1389(4) 0.5140(3) 0.3346(2) 0.0133(5) Uiso 0.9 1 d D . P A 1
C1A C 0.202(3) 0.547(2) 0.3625(15) 0.009(4) Uiso 0.1 1 d D . P A 2
C2 C 0.0992(6) 0.4666(4) 0.1989(3) 0.0131(10) Uiso 0.9 1 d D . P A 1
H2 H -0.0289 0.4015 0.1629 0.016 Uiso 0.9 1 calc R . P A 1
C2A C 0.406(3) 0.626(3) 0.3305(15) 0.014(7) Uiso 0.1 1 d D . P A 2
H2A H 0.5104 0.6765 0.3946 0.017 Uiso 0.1 1 calc R . P A 2
C3 C 0.2864(4) 0.5345(3) 0.1275(2) 0.0205(5) Uani 1 1 d D . . . .
H3B H 0.2885 0.5130 0.0365 0.025 Uiso 0.1 1 calc R . P A 2
H3A H 0.301(5) 0.524(4) 0.037(3) 0.025 Uiso 0.9 1 d R . P B 1
C4 C 0.4500(4) 0.6254(3) 0.2001(2) 0.0191(5) Uani 1 1 d D . . . .
H4B H 0.5789 0.6820 0.1651 0.023 Uiso 0.1 1 calc R . P A 2
H4A H 0.588(5) 0.682(4) 0.174(3) 0.023 Uiso 0.9 1 d R . P C 1
C5 C -0.0137(4) 0.4728(3) 0.4375(2) 0.0156(5) Uiso 0.92 1 d D . P A 1
H5 H -0.1443 0.4012 0.4148 0.019 Uiso 0.92 1 calc R . P A 1
C5A C 0.093(4) 0.536(3) 0.488(2) 0.019(5) Uiso 0.08 1 d D . P A 2
H5A H 0.1745 0.5902 0.5598 0.023 Uiso 0.08 1 calc R . P A 2


_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 1.736(3) . ?
S1 C4 1.704(2) . ?
S1A C1A 1.674(16) . ?
S1A C3 1.658(9) . ?
C1 C2 1.445(4) . ?
C1 C5 1.452(3) . ?
C1A C2A 1.381(14) . ?
C1A C5A 1.472(17) . ?
C2 C3 1.440(4) . ?
C2A C4 1.379(14) . ?
C3 C4 1.360(3) . ?
C5 C5 1.349(4) 3_566 ?
C5A C5A 1.24(5) 3_566 ?

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 92.47(11) . . ?
C3 S1A C1A 96.9(7) . . ?
C2 C1 S1 111.4(2) . . ?
C2 C1 C5 125.4(3) . . ?
C5 C1 S1 123.13(19) . . ?
C2A C1A S1A 105.7(12) . . ?
C2A C1A C5A 130.9(17) . . ?
C5A C1A S1A 123.4(16) . . ?
C3 C2 C1 108.7(3) . . ?
C4 C2A C1A 116.1(15) . . ?
C4 C3 S1A 109.4(3) . . ?
C4 C3 C2 115.1(2) . . ?
C3 C4 S1 112.29(17) . . ?
C3 C4 C2A 111.8(9) . . ?
C5 C5 C1 125.8(3) 3_566 . ?
C5A C5A C1A 129(3) 3_566 . ?

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
S1 C1 C2 C3 0.5(3) . . . . ?
S1 C1 C5 C5 2.9(4) . . . 3_566 ?
S1A C1A C2A C4 3.0(16) . . . . ?
S1A C1A C5A C5A 2(5) . . . 3_566 ?
S1A C3 C4 C2A 3.6(10) . . . . ?
C1 S1 C4 C3 -0.04(17) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C1A S1A C3 C4 -1.7(7) . . . . ?
C1A C2A C4 C3 -4.5(16) . . . . ?
C2 C1 C5 C5 -175.0(3) . . . 3_566 ?
C2 C3 C4 S1 0.4(3) . . . . ?
C2A C1A C5A C5A 180(3) . . . 3_566 ?
C3 S1A C1A C2A -0.7(10) . . . . ?
C3 S1A C1A C5A 177.2(15) . . . . ?
C4 S1 C1 C2 -0.30(19) . . . . ?
C4 S1 C1 C5 -178.45(19) . . . . ?
C5 C1 C2 C3 178.6(2) . . . . ?
C5A C1A C2A C4 -174.7(18) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-07-02
_olex2_submission_special_instructions 'No special instructions were received'
_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_lucia8cult
_database_code_depnum_ccdc_archive 'CCDC 1509232'
_audit_update_record             
;
2016-11-25 deposited with the CCDC.
2017-01-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT230_lucia8cult          
;
PROBLEM: Hirshfeld Test Diff for    C32    --  C33     ..        7.6 s.u.
RESPONSE: problem due to the extensively disorder structure
;
# Added during the CSD deposition process: Friday 25 November 2016 06:05 AM
# end Validation Reply Form

_audit_creation_date             2016-02-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
4,5-bis(thiophene-2-yl)thieno[3,2-e]benzo[b]thiophene
_chemical_formula_moiety         'C18 H10 S4'
_chemical_formula_sum            'C18 H10 S4'
_chemical_formula_weight         354.50
_chemical_melting_point          ?

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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.91901(14)
_cell_length_b                   8.76755(11)
_cell_length_c                   15.8755(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.1272(11)
_cell_angle_gamma                90
_cell_volume                     1517.54(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5807
_cell_measurement_temperature    100.1(5)
_cell_measurement_theta_max      75.3490
_cell_measurement_theta_min      4.7830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.668
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange

_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
There is a disorder along the rotation axis of the thiophene group 
S(4), C(41), C(42), C(43) and C(44) which parallel to the bond C(1) and 
C(41), in which the positions of S(4) and C(42) are interconvertible.  
The occupancies of part1 (i.e S(4) and C(42)) and part2 (named S(4A) 
and C(42A)) were found to be 0.55 and 0.45 respectively.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_unetI/netI     0.0161

_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7920

_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.998
_diffrn_reflns_theta_min         4.796
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.1(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -44.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203   37.0000  120.0000 77

#__ type_ start__ end____ width___ exp.time_
  2 omega   23.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8203 -125.0000 -120.0000 75

#__ type_ start__ end____ width___ exp.time_
  3 omega   30.00  107.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000 -180.0000 77

#__ type_ start__ end____ width___ exp.time_
  4 omega   61.00  115.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000  -60.0000 54

#__ type_ start__ end____ width___ exp.time_
  5 omega   50.00   91.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000    0.0000 41

#__ type_ start__ end____ width___ exp.time_
  6 omega   39.00  144.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -77.0000    0.0000 105

#__ type_ start__ end____ width___ exp.time_
  7 omega   87.00  161.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000   60.0000 74

#__ type_ start__ end____ width___ exp.time_
  8 omega   48.00   91.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  120.0000 43

#__ type_ start__ end____ width___ exp.time_
  9 omega   37.00   96.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000  -90.0000 59

#__ type_ start__ end____ width___ exp.time_
 10 omega   49.00  172.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   15.0000 -180.0000 123

#__ type_ start__ end____ width___ exp.time_
 11 omega   43.00   78.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
 12 omega   40.00   86.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
 13 omega -113.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203  -57.0000 -120.0000 102

#__ type_ start__ end____ width___ exp.time_
 14 omega -117.00  -21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203  -37.0000  -30.0000 96
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0620251000
_diffrn_orient_matrix_UB_12      -0.0316710000
_diffrn_orient_matrix_UB_13      -0.0877824000
_diffrn_orient_matrix_UB_21      -0.0376777000
_diffrn_orient_matrix_UB_22      0.1690899000
_diffrn_orient_matrix_UB_23      -0.0075994000
_diffrn_orient_matrix_UB_31      0.1212772000
_diffrn_orient_matrix_UB_32      0.0365007000
_diffrn_orient_matrix_UB_33      -0.0407916000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2556
_reflns_number_total             2681
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2681
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0261
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0350P)²+1.0490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0661
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C42) = Uanis(S4A)
Uanis(C42A) = Uanis(S4)
3. Others
 Fixed Sof: S4(0.55) S4A(0.45) C42(0.55) H42(0.55) C42A(0.45) H42A(0.45)
 H43A(0.45) H43(0.55) H44(0.55) H44A(0.45)
4.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C23(H23), C24(H24), C32(H32), C33(H33), C34(H34),
 C42(H42), C42A(H42A), C43(H43A), C43(H43), C44(H44), C44(H44A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.12758(3) 0.31138(4) 0.07903(2) 0.01841(11) Uani 1 1 d . . . . .
S2 S 0.63159(3) 0.45766(4) 0.25827(2) 0.01834(11) Uani 1 1 d . . . . .
S3 S 0.52546(4) 0.83280(4) 0.19735(2) 0.02122(11) Uani 1 1 d . . . . .
S4 S 0.23994(12) 0.57295(13) -0.06088(5) 0.0203(2) Uani 0.55 1 d . . P A 1
S4A S 0.22426(15) 0.79859(13) 0.07401(9) 0.0177(3) Uani 0.45 1 d . . P A 2
C1 C 0.32574(14) 0.51198(17) 0.10381(9) 0.0149(3) Uani 1 1 d . . . . .
C2 C 0.43939(14) 0.54542(17) 0.14395(9) 0.0152(3) Uani 1 1 d . . . . .
C11 C 0.26892(14) 0.37193(17) 0.12230(9) 0.0155(3) Uani 1 1 d . . . . .
C12 C 0.31936(14) 0.26545(17) 0.18048(9) 0.0160(3) Uani 1 1 d . . . . .
C13 C 0.24195(15) 0.13459(18) 0.18810(10) 0.0187(3) Uani 1 1 d . . . . .
H13 H 0.2613 0.0504 0.2240 0.022 Uiso 1 1 calc R . . . .
C14 C 0.13751(15) 0.14546(18) 0.13774(10) 0.0205(3) Uani 1 1 d . . . . .
H14 H 0.0758 0.0690 0.1351 0.025 Uiso 1 1 calc R . . . .
C21 C 0.49119(14) 0.43837(17) 0.20237(9) 0.0155(3) Uani 1 1 d . . . . .
C22 C 0.43434(14) 0.30035(17) 0.22238(9) 0.0162(3) Uani 1 1 d . . . . .
C23 C 0.50576(15) 0.21412(18) 0.28465(10) 0.0197(3) Uani 1 1 d . . . . .
H23 H 0.4809 0.1188 0.3065 0.024 Uiso 1 1 calc R . . . .
C24 C 0.61256(15) 0.28477(18) 0.30854(10) 0.0220(3) Uani 1 1 d . . . . .
H24 H 0.6710 0.2435 0.3488 0.026 Uiso 1 1 calc R . . . .
C31 C 0.50405(13) 0.68770(17) 0.12429(9) 0.0156(3) Uani 1 1 d . . . . .
C32 C 0.54718(13) 0.73082(17) 0.04648(10) 0.0159(3) Uani 1 1 d . . . . .
H32 H 0.5423 0.6686 -0.0026 0.019 Uiso 1 1 calc R . . . .
C33 C 0.59936(14) 0.87957(19) 0.05003(10) 0.0215(3) Uani 1 1 d . . . . .
H33 H 0.6351 0.9266 0.0034 0.026 Uiso 1 1 calc R . . . .
C34 C 0.59324(15) 0.94804(19) 0.12643(11) 0.0222(3) Uani 1 1 d . . . . .
H34 H 0.6230 1.0478 0.1390 0.027 Uiso 1 1 calc R . . . .
C41 C 0.26441(13) 0.61953(17) 0.04354(9) 0.0160(3) Uani 1 1 d . . . . .
C42 C 0.2243(6) 0.7623(6) 0.0593(4) 0.0177(3) Uani 0.55 1 d . . P A 1
H42 H 0.2283 0.8079 0.1137 0.021 Uiso 0.55 1 calc R . P A 1
C42A C 0.2399(7) 0.5961(9) -0.0402(4) 0.0203(2) Uani 0.45 1 d . . P A 2
H42A H 0.2567 0.5039 -0.0688 0.024 Uiso 0.45 1 calc R . P A 2
C43 C 0.17208(15) 0.84147(19) -0.02020(11) 0.0226(3) Uani 1 1 d . . . . .
H43A H 0.1354 0.9382 -0.0312 0.027 Uiso 0.45 1 calc R . P A 2
H43 H 0.1400 0.9420 -0.0245 0.027 Uiso 0.55 1 calc R . P A 1
C44 C 0.18082(15) 0.7393(2) -0.08318(10) 0.0235(4) Uani 1 1 d . . . . .
H44 H 0.1531 0.7640 -0.1393 0.028 Uiso 0.55 1 calc R . P A 1
H44A H 0.1563 0.7522 -0.1411 0.028 Uiso 0.45 1 calc R . P A 2


_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 C11 1.7378(15) . ?
S1 C14 1.7280(16) . ?
S2 C21 1.7372(15) . ?
S2 C24 1.7308(17) . ?
S3 C31 1.7288(15) . ?
S3 C34 1.7108(17) . ?
S4 C41 1.7140(16) . ?
S4 C44 1.626(2) . ?
S4A C41 1.7069(17) . ?
S4A C43 1.615(2) . ?
C1 C2 1.395(2) . ?
C1 C11 1.414(2) . ?
C1 C41 1.478(2) . ?
C2 C21 1.416(2) . ?
C2 C31 1.475(2) . ?
C11 C12 1.405(2) . ?
C12 C13 1.434(2) . ?
C12 C22 1.422(2) . ?
C13 C14 1.360(2) . ?
C21 C22 1.404(2) . ?
C22 C23 1.440(2) . ?
C23 C24 1.356(2) . ?
C31 C32 1.398(2) . ?
C32 C33 1.423(2) . ?
C33 C34 1.358(2) . ?
C41 C42 1.354(6) . ?
C41 C42A 1.357(7) . ?
C42 C43 1.524(7) . ?
C42A C44 1.553(8) . ?
C43 C44 1.350(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 S1 C11 90.90(7) . . ?
C24 S2 C21 91.46(8) . . ?
C34 S3 C31 92.33(8) . . ?
C44 S4 C41 92.06(9) . . ?
C43 S4A C41 91.99(9) . . ?
C2 C1 C11 118.51(14) . . ?
C2 C1 C41 121.48(13) . . ?
C11 C1 C41 120.01(13) . . ?
C1 C2 C21 118.27(14) . . ?
C1 C2 C31 120.35(13) . . ?
C21 C2 C31 121.37(13) . . ?
C1 C11 S1 125.00(12) . . ?
C12 C11 S1 111.40(11) . . ?
C12 C11 C1 123.58(14) . . ?
C11 C12 C13 112.05(14) . . ?
C11 C12 C22 117.99(14) . . ?
C22 C12 C13 129.96(14) . . ?
C14 C13 C12 111.94(14) . . ?
C13 C14 S1 113.70(12) . . ?
C2 C21 S2 125.46(12) . . ?
C22 C21 S2 110.91(11) . . ?
C22 C21 C2 123.63(14) . . ?
C12 C22 C23 129.77(15) . . ?
C21 C22 C12 118.01(14) . . ?
C21 C22 C23 112.23(14) . . ?
C24 C23 C22 112.18(14) . . ?
C23 C24 S2 113.20(12) . . ?
C2 C31 S3 121.95(11) . . ?
C32 C31 S3 110.73(11) . . ?
C32 C31 C2 127.15(13) . . ?
C31 C32 C33 111.49(14) . . ?
C34 C33 C32 113.66(14) . . ?
C33 C34 S3 111.76(12) . . ?
C1 C41 S4 121.03(12) . . ?
C1 C41 S4A 121.18(12) . . ?
C42 C41 S4 111.4(3) . . ?
C42 C41 C1 127.6(3) . . ?
C42A C41 S4A 112.1(4) . . ?
C42A C41 C1 126.6(4) . . ?
C41 C42 C43 112.2(4) . . ?
C41 C42A C44 111.3(5) . . ?
C44 C43 S4A 119.72(14) . . ?
C44 C43 C42 105.9(2) . . ?
C43 C44 S4 118.50(13) . . ?
C43 C44 C42A 104.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C11 C12 C13 0.67(16) . . . . ?
S1 C11 C12 C22 -178.95(11) . . . . ?
S2 C21 C22 C12 -178.68(11) . . . . ?
S2 C21 C22 C23 1.24(16) . . . . ?
S3 C31 C32 C33 1.62(16) . . . . ?
S4 C41 C42 C43 -1.4(5) . . . . ?
S4A C41 C42A C44 -0.7(6) . . . . ?
S4A C43 C44 C42A 2.3(4) . . . . ?
C1 C2 C21 S2 179.55(11) . . . . ?
C1 C2 C21 C22 -0.2(2) . . . . ?
C1 C2 C31 S3 112.33(14) . . . . ?
C1 C2 C31 C32 -62.5(2) . . . . ?
C1 C11 C12 C13 179.07(14) . . . . ?
C1 C11 C12 C22 -0.6(2) . . . . ?
C1 C41 C42 C43 176.8(2) . . . . ?
C1 C41 C42A C44 -176.9(2) . . . . ?
C2 C1 C11 S1 179.64(11) . . . . ?
C2 C1 C11 C12 1.5(2) . . . . ?
C2 C1 C41 S4 115.15(15) . . . . ?
C2 C1 C41 S4A -60.68(19) . . . . ?
C2 C1 C41 C42 -62.8(4) . . . . ?
C2 C1 C41 C42A 115.2(5) . . . . ?
C2 C21 C22 C12 1.1(2) . . . . ?
C2 C21 C22 C23 -178.99(14) . . . . ?
C2 C31 C32 C33 176.92(14) . . . . ?
C11 S1 C14 C13 0.11(13) . . . . ?
C11 C1 C2 C21 -1.1(2) . . . . ?
C11 C1 C2 C31 177.81(13) . . . . ?
C11 C1 C41 S4 -65.22(18) . . . . ?
C11 C1 C41 S4A 118.95(15) . . . . ?
C11 C1 C41 C42 116.8(4) . . . . ?
C11 C1 C41 C42A -65.2(5) . . . . ?
C11 C12 C13 C14 -0.60(19) . . . . ?
C11 C12 C22 C21 -0.7(2) . . . . ?
C11 C12 C22 C23 179.39(15) . . . . ?
C12 C13 C14 S1 0.26(18) . . . . ?
C12 C22 C23 C24 178.81(15) . . . . ?
C13 C12 C22 C21 179.76(15) . . . . ?
C13 C12 C22 C23 -0.1(3) . . . . ?
C14 S1 C11 C1 -178.81(14) . . . . ?
C14 S1 C11 C12 -0.45(12) . . . . ?
C21 S2 C24 C23 0.21(13) . . . . ?
C21 C2 C31 S3 -68.83(18) . . . . ?
C21 C2 C31 C32 116.35(17) . . . . ?
C21 C22 C23 C24 -1.1(2) . . . . ?
C22 C12 C13 C14 178.96(15) . . . . ?
C22 C23 C24 S2 0.46(18) . . . . ?
C24 S2 C21 C2 179.40(14) . . . . ?
C24 S2 C21 C22 -0.84(12) . . . . ?
C31 S3 C34 C33 0.13(13) . . . . ?
C31 C2 C21 S2 0.7(2) . . . . ?
C31 C2 C21 C22 -179.04(14) . . . . ?
C31 C32 C33 C34 -1.58(19) . . . . ?
C32 C33 C34 S3 0.80(18) . . . . ?
C34 S3 C31 C2 -176.61(13) . . . . ?
C34 S3 C31 C32 -1.02(12) . . . . ?
C41 S4 C44 C43 -0.42(16) . . . . ?
C41 S4A C43 C44 -2.43(17) . . . . ?
C41 C1 C2 C21 178.57(13) . . . . ?
C41 C1 C2 C31 -2.6(2) . . . . ?
C41 C1 C11 S1 0.0(2) . . . . ?
C41 C1 C11 C12 -178.17(14) . . . . ?
C41 C42 C43 C44 1.0(5) . . . . ?
C41 C42A C44 C43 -0.9(6) . . . . ?
C42 C43 C44 S4 -0.3(3) . . . . ?
C43 S4A C41 C1 178.06(13) . . . . ?
C43 S4A C41 C42A 1.7(4) . . . . ?
C44 S4 C41 C1 -177.22(13) . . . . ?
C44 S4 C41 C42 1.0(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-02-19
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'the cystal has been formed after spountanueus evaporation of hexane in which the sample was dissolved'
####################################################################### 
# 
# 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_lucia1cult
_database_code_depnum_ccdc_archive 'CCDC 1509230'
_audit_update_record             
;
2016-11-25 deposited with the CCDC.
2017-01-11 downloaded from the CCDC.
;
_audit_creation_date             2016-06-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            'Tetrathienylethene, TTE'
_chemical_name_systematic        '1,1,2,2-tetra(thiophen-2-yl)ethene '
_chemical_formula_moiety         'C18 H12 S4'
_chemical_formula_sum            'C18 H12 S4'
_chemical_formula_weight         356.52
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H12 S4'
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 Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.3160(2)
_cell_length_b                   9.10329(18)
_cell_length_c                   9.6346(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.853(3)
_cell_angle_gamma                90
_cell_volume                     763.55(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2882
_cell_measurement_temperature    100.0(4)
_cell_measurement_theta_max      75.1660
_cell_measurement_theta_min      5.6630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.633
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3786
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.967
_diffrn_reflns_theta_min         6.917
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   44.00   82.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  -90.0000 38

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   35.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8828   37.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega  -95.00   -3.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8828  125.0000   30.0000 92

#__ type_ start__ end____ width___ exp.time_
  4 omega -114.00  -11.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8828  -57.0000 -180.0000 103

#__ type_ start__ end____ width___ exp.time_
  5 omega   33.00   87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000   90.0000 54

#__ type_ start__ end____ width___ exp.time_
  6 omega   43.00  103.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000   90.0000 60

#__ type_ start__ end____ width___ exp.time_
  7 omega   57.00   97.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000  -30.0000 40

#__ type_ start__ end____ width___ exp.time_
  8 omega   35.00  108.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  -30.0000 73

#__ type_ start__ end____ width___ exp.time_
  9 omega   37.00  110.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -125.0000  -60.0000 73

#__ type_ start__ end____ width___ exp.time_
 10 omega   40.00   87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000   60.0000 47

#__ type_ start__ end____ width___ exp.time_
 11 omega   41.00   87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000  150.0000 46

#__ type_ start__ end____ width___ exp.time_
 12 omega   83.00  173.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   45.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
 13 omega  142.00  178.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  125.0000  -60.0000 36

#__ type_ start__ end____ width___ exp.time_
 14 omega   96.00  122.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  125.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   80.00  166.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   61.0000   90.0000 86
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1531678000
_diffrn_orient_matrix_UB_12      0.0227791000
_diffrn_orient_matrix_UB_13      0.0244381000
_diffrn_orient_matrix_UB_21      -0.0842245000
_diffrn_orient_matrix_UB_22      0.0134421000
_diffrn_orient_matrix_UB_23      -0.1691096000
_diffrn_orient_matrix_UB_31      -0.0275940000
_diffrn_orient_matrix_UB_32      -0.1670812000
_diffrn_orient_matrix_UB_33      -0.0105166000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1257
_reflns_number_total             1319
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     106
_refine_ls_number_reflns         1319
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0250
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0678P)²+0.0559P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0798
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Shared sites
{S2, C7A}
3. Restrained distances
 S2-C6 = S2-C9
 1.66 with sigma of 0.03
4. Uiso/Uaniso restraints and constraints
Uanis(C1A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.002
Uanis(S2) = Uanis(C7A)
Uanis(S2A) = Uanis(C7)
Uanis(C1A) = Uanis(C1)
5. Others
 Fixed Sof: S2(0.935) S2A(0.065) C1(0.935) C1A(0.065) C7(0.935) H7(0.935)
 C7A(0.065) H7A(0.065) H8B(0.065) H8A(0.935) H9A(0.935) H9B(0.065)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C7A(H7A), C8(H8B), C8(H8A), C9(H9A), C9(H9B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.25872(4) 0.15541(3) 0.42074(4) 0.01373(16) Uani 1 1 d . . . . .
S2 S 0.10279(4) -0.00229(4) 0.83529(4) 0.01709(16) Uani 0.935 1 d D . P A 1
S2A S 0.085(3) 0.280(2) 0.704(2) 0.0150(7) Uani 0.065 1 d . . P A 2
C1 C 0.03310(16) 0.06473(16) 0.52896(16) 0.0113(3) Uani 0.935 1 d . . P A 1
C1A C 0.005(2) -0.015(2) 0.579(2) 0.0113(3) Uani 0.065 1 d . U P A 2
C2 C 0.07992(16) 0.17219(14) 0.43561(16) 0.0136(3) Uani 1 1 d . . . . .
C3 C 0.00412(16) 0.29505(15) 0.36156(16) 0.0152(3) Uani 1 1 d . . . . .
H3 H -0.0948 0.3248 0.3581 0.018 Uiso 1 1 calc R . . . .
C4 C 0.09305(16) 0.37239(15) 0.29035(16) 0.0142(3) Uani 1 1 d . . . . .
H4 H 0.0584 0.4589 0.2330 0.017 Uiso 1 1 calc R . . . .
C5 C 0.23162(17) 0.30961(15) 0.31316(16) 0.0149(3) Uani 1 1 d . . . . .
H5 H 0.3047 0.3468 0.2741 0.018 Uiso 1 1 calc R . . . .
C6 C 0.06927(15) 0.11233(15) 0.68406(16) 0.0128(3) Uani 1 1 d D . . . .
C7 C 0.0896(7) 0.2615(6) 0.7297(5) 0.0150(7) Uani 0.935 1 d . . P A 1
H7 H 0.0774 0.3426 0.6645 0.018 Uiso 0.935 1 calc R . P A 1
C7A C 0.10279(4) -0.00229(4) 0.83529(4) 0.01709(16) Uani 0.065 1 d . . P A 2
H7A H 0.1000 -0.1058 0.8466 0.021 Uiso 0.065 1 calc R . P A 2
C8 C 0.13097(16) 0.27335(16) 0.88775(17) 0.0169(3) Uani 1 1 d . . . . .
H8B H 0.1490 0.3616 0.9441 0.020 Uiso 0.065 1 calc R . P A 2
H8A H 0.1484 0.3645 0.9391 0.020 Uiso 0.935 1 calc R . P A 1
C9 C 0.14278(17) 0.14142(16) 0.95654(17) 0.0169(3) Uani 1 1 d D . . . .
H9A H 0.1703 0.1304 1.0609 0.020 Uiso 0.935 1 calc R . P A 1
H9B H 0.1703 0.1304 1.0609 0.020 Uiso 0.065 1 calc R . P A 2


_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 C2 1.7287(14) . ?
S1 C5 1.7095(14) . ?
S2 C6 1.7278(14) . ?
S2 C9 1.7044(15) . ?
S2A C6 1.54(2) . ?
S2A C8 1.66(2) . ?
C1 C1 1.355(3) 3_556 ?
C1 C2 1.4951(19) . ?
C1 C6 1.475(2) . ?
C1A C1A 1.52(4) 3_556 ?
C1A C2 1.62(2) 3_556 ?
C1A C6 1.51(2) . ?
C2 C1A 1.62(2) 3_556 ?
C2 C3 1.378(2) . ?
C3 C4 1.4343(19) . ?
C4 C5 1.356(2) . ?
C6 C7 1.419(6) . ?
C6 C7A 1.7278(14) . ?
C7 C8 1.435(5) . ?
C7A C9 1.7044(15) . ?
C8 C9 1.357(2) . ?

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
C5 S1 C2 92.24(7) . . ?
C9 S2 C6 92.54(7) . . ?
C6 S2A C8 94.4(9) . . ?
C1 C1 C2 120.59(16) 3_556 . ?
C1 C1 C6 125.38(16) 3_556 . ?
C6 C1 C2 114.01(13) . . ?
C1A C1A C2 102(2) 3_556 3_556 ?
C6 C1A C1A 114(2) . 3_556 ?
C6 C1A C2 143.3(15) . 3_556 ?
C1 C2 S1 119.21(10) . . ?
C1A C2 S1 111.8(7) 3_556 . ?
C3 C2 S1 111.10(10) . . ?
C3 C2 C1 129.56(13) . . ?
C3 C2 C1A 121.8(7) . 3_556 ?
C2 C3 C4 111.67(13) . . ?
C5 C4 C3 113.21(12) . . ?
C4 C5 S1 111.77(10) . . ?
S2A C6 C7A 120.7(8) . . ?
C1 C6 S2 125.76(10) . . ?
C1A C6 S2A 147.4(11) . . ?
C1A C6 C7A 90.5(8) . . ?
C7 C6 S2 110.62(17) . . ?
C7 C6 C1 123.53(19) . . ?
C6 C7 C8 110.9(2) . . ?
C9 C7A C6 92.54(7) . . ?
C9 C8 S2A 119.8(8) . . ?
C9 C8 C7 113.3(2) . . ?
C8 C9 S2 112.62(11) . . ?
C8 C9 C7A 112.62(11) . . ?

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
S1 C2 C3 C4 1.33(16) . . . . ?
S2 C6 C7 C8 -0.4(5) . . . . ?
S2A C6 C7A C9 0.3(10) . . . . ?
S2A C8 C9 C7A -1.1(10) . . . . ?
C1 C1 C2 S1 -86.3(2) 3_556 . . . ?
C1 C1 C2 C3 98.2(2) 3_556 . . . ?
C1 C1 C6 S2 25.5(2) 3_556 . . . ?
C1 C1 C6 C7 -158.2(3) 3_556 . . . ?
C1 C2 C3 C4 177.15(14) . . . . ?
C1 C6 C7 C8 -177.2(2) . . . . ?
C1A C1A C6 S2A 32(3) 3_556 . . . ?
C1A C1A C6 C7A -163.8(19) 3_556 . . . ?
C1A C2 C3 C4 -133.7(9) 3_556 . . . ?
C1A C6 C7A C9 -169.7(7) . . . . ?
C2 S1 C5 C4 0.55(12) . . . . ?
C2 C1 C6 S2 -153.06(11) . . . . ?
C2 C1 C6 C7 23.3(3) . . . . ?
C2 C1A C6 S2A -137(2) 3_556 . . . ?
C2 C1A C6 C7A 27(2) 3_556 . . . ?
C2 C3 C4 C5 -0.95(19) . . . . ?
C3 C4 C5 S1 0.12(17) . . . . ?
C5 S1 C2 C1 -177.40(12) . . . . ?
C5 S1 C2 C1A 138.6(8) . . . 3_556 ?
C5 S1 C2 C3 -1.09(12) . . . . ?
C6 S2 C9 C8 0.43(12) . . . . ?
C6 S2A C8 C9 1.1(14) . . . . ?
C6 C1 C2 S1 92.30(13) . . . . ?
C6 C1 C2 C3 -83.24(19) . . . . ?
C6 C7 C8 C9 0.7(5) . . . . ?
C6 C7A C9 C8 0.43(12) . . . . ?
C7 C8 C9 S2 -0.7(3) . . . . ?
C8 S2A C6 C1A 160.5(16) . . . . ?
C8 S2A C6 C7A -0.8(14) . . . . ?
C9 S2 C6 C1 176.72(12) . . . . ?
C9 S2 C6 C7 0.0(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2015-02-17
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       ', Luminescent'
