# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_150702_xiamin_0630
_audit_block_doi                 10.5517/ccdc.csd.cc1lpsqs
_database_code_depnum_ccdc_archive 'CCDC 1480706'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CP01281K 2017
2 10.1039/C6TC02618D 2016
_audit_update_record             
;
2016-05-18 deposited with the CCDC.
2017-11-13 downloaded from the CCDC.
;
_audit_creation_date             2015-07-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
"(E)-2'-[2-(benzo[d]thiazol-2-yl)vinyl]-N, N-dimethyl-(1,1'-biphenyl)-4-amine"
_chemical_formula_moiety         'C23 H20 N2 S'
_chemical_formula_sum            'C23 H20 N2 S'
_chemical_formula_weight         356.47
_chemical_melting_point          388.05-389.45
_chemical_oxdiff_formula         'c10 h10 n2 o2'
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'
N N 0.0061 0.0033 '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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   12.5537(8)
_cell_length_b                   6.3103(4)
_cell_length_c                   23.6534(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.738(6)
_cell_angle_gamma                90.00
_cell_volume                     1846.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1938
_cell_measurement_temperature    170.
_cell_measurement_theta_max      29.6016
_cell_measurement_theta_min      3.2218
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7064
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.34
_diffrn_ambient_temperature      170.
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0424385000
_diffrn_orient_matrix_UB_12      -0.0142350000
_diffrn_orient_matrix_UB_13      0.0159793000
_diffrn_orient_matrix_UB_21      -0.0371176000
_diffrn_orient_matrix_UB_22      -0.0145711000
_diffrn_orient_matrix_UB_23      -0.0258398000
_diffrn_orient_matrix_UB_31      0.0103876000
_diffrn_orient_matrix_UB_32      -0.1105918000
_diffrn_orient_matrix_UB_33      0.0013639000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2598
_reflns_number_total             3377
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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         0.267
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3377
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0432P)²+0.6367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1125
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C17(H17), C18(H18), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.14051(4) 0.19230(9) 0.07992(2) 0.03735(18) Uani 1 d . . .
N1 N 0.12174(13) 0.1842(3) 0.18831(7) 0.0307(4) Uani 1 d . . .
N2 N 0.27346(13) 0.5828(3) -0.14839(7) 0.0332(4) Uani 1 d . . .
C1 C 0.06474(16) -0.0079(3) 0.10266(10) 0.0353(5) Uani 1 d . . .
C2 C 0.01166(19) -0.1753(4) 0.07123(12) 0.0519(7) Uani 1 d . . .
H2 H 0.0136 -0.1919 0.0315 0.062 Uiso 1 calc . . R
C3 C -0.04454(19) -0.3178(4) 0.10061(15) 0.0616(9) Uani 1 d . . .
H3 H -0.0820 -0.4335 0.0806 0.074 Uiso 1 calc . . R
C4 C -0.04600(19) -0.2920(4) 0.15814(15) 0.0615(8) Uani 1 d . . .
H4 H -0.0848 -0.3913 0.1770 0.074 Uiso 1 calc . . R
C5 C 0.00593(17) -0.1298(4) 0.18915(12) 0.0496(7) Uani 1 d . . .
H5 H 0.0030 -0.1151 0.2288 0.060 Uiso 1 calc . . R
C6 C 0.06361(16) 0.0146(4) 0.16128(10) 0.0366(5) Uani 1 d . . .
C7 C 0.16694(15) 0.2905(3) 0.14969(9) 0.0293(5) Uani 1 d . . .
C8 C 0.23670(16) 0.4726(3) 0.16261(9) 0.0324(5) Uani 1 d . . .
H8 H 0.2584 0.5107 0.2017 0.039 Uiso 1 calc . . R
C9 C 0.27214(15) 0.5893(3) 0.12313(9) 0.0291(5) Uani 1 d . . .
H9 H 0.2466 0.5491 0.0845 0.035 Uiso 1 calc . . R
C10 C 0.34535(15) 0.7719(3) 0.13074(9) 0.0285(5) Uani 1 d . . .
C11 C 0.38028(16) 0.8578(3) 0.18552(9) 0.0353(5) Uani 1 d . . .
H11 H 0.3583 0.7933 0.2180 0.042 Uiso 1 calc . . R
C12 C 0.44587(17) 1.0340(4) 0.19302(10) 0.0412(6) Uani 1 d . . .
H12 H 0.4684 1.0907 0.2303 0.049 Uiso 1 calc . . R
C13 C 0.47890(17) 1.1280(4) 0.14618(11) 0.0414(6) Uani 1 d . . .
H13 H 0.5239 1.2500 0.1512 0.050 Uiso 1 calc . . R
C14 C 0.44662(16) 1.0451(3) 0.09215(10) 0.0354(5) Uani 1 d . . .
H14 H 0.4703 1.1103 0.0602 0.043 Uiso 1 calc . . R
C15 C 0.37972(15) 0.8669(3) 0.08336(9) 0.0290(5) Uani 1 d . . .
C16 C 0.34715(15) 0.7874(3) 0.02353(9) 0.0284(5) Uani 1 d . . .
C17 C 0.37296(15) 0.5838(3) 0.00728(9) 0.0315(5) Uani 1 d . . .
H17 H 0.4080 0.4893 0.0357 0.038 Uiso 1 calc . . R
C18 C 0.34912(15) 0.5157(3) -0.04876(9) 0.0318(5) Uani 1 d . . .
H18 H 0.3695 0.3769 -0.0582 0.038 Uiso 1 calc . . R
C19 C 0.29534(14) 0.6474(3) -0.09198(9) 0.0282(5) Uani 1 d . . .
C20 C 0.26595(16) 0.8501(3) -0.07528(9) 0.0325(5) Uani 1 d . . .
H20 H 0.2271 0.9427 -0.1031 0.039 Uiso 1 calc . . R
C21 C 0.29258(16) 0.9160(3) -0.01942(9) 0.0319(5) Uani 1 d . . .
H21 H 0.2729 1.0551 -0.0098 0.038 Uiso 1 calc . . R
C22 C 0.22346(18) 0.7282(4) -0.19197(9) 0.0405(5) Uani 1 d . . .
H22A H 0.1546 0.7776 -0.1825 0.061 Uiso 1 calc . . GR
H22B H 0.2104 0.6562 -0.2292 0.061 Uiso 1 calc . . GR
H22C H 0.2714 0.8497 -0.1938 0.061 Uiso 1 calc . . GR
C23 C 0.31755(18) 0.3857(4) -0.16612(10) 0.0415(6) Uani 1 d . . .
H23A H 0.3967 0.3924 -0.1584 0.062 Uiso 1 calc . . GR
H23B H 0.2927 0.3640 -0.2073 0.062 Uiso 1 calc . . GR
H23C H 0.2931 0.2676 -0.1447 0.062 Uiso 1 calc . . GR


_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(2) . ?
S1 C7 1.741(2) . ?
N1 C6 1.389(3) . ?
N1 C7 1.335(3) . ?
N2 C19 1.378(3) . ?
N2 C22 1.442(3) . ?
N2 C23 1.452(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.396(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.398(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.374(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.360(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(3) . ?
C7 C8 1.446(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.324(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.466(3) . ?
C10 C11 1.405(3) . ?
C10 C15 1.402(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.377(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.377(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.398(3) . ?
C15 C16 1.492(3) . ?
C16 C17 1.395(3) . ?
C16 C21 1.387(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.378(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.400(3) . ?
C19 C20 1.406(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.372(3) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C7 89.53(10) . . ?
C7 N1 C6 108.86(18) . . ?
C19 N2 C22 119.66(17) . . ?
C19 N2 C23 120.68(17) . . ?
C22 N2 C23 118.68(18) . . ?
C2 C1 S1 129.0(2) . . ?
C2 C1 C6 121.5(2) . . ?
C6 C1 S1 109.55(16) . . ?
C1 C2 H2 121.4 . . ?
C1 C2 C3 117.3(3) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 118.7 . . ?
C5 C4 C3 122.6(3) . . ?
C5 C4 H4 118.7 . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.4(3) . . ?
C6 C5 H5 120.8 . . ?
N1 C6 C1 116.27(19) . . ?
N1 C6 C5 124.0(2) . . ?
C1 C6 C5 119.7(2) . . ?
N1 C7 S1 115.77(15) . . ?
N1 C7 C8 124.55(19) . . ?
C8 C7 S1 119.65(15) . . ?
C7 C8 H8 118.1 . . ?
C9 C8 C7 123.8(2) . . ?
C9 C8 H8 118.1 . . ?
C8 C9 H9 115.5 . . ?
C8 C9 C10 129.0(2) . . ?
C10 C9 H9 115.5 . . ?
C11 C10 C9 120.53(19) . . ?
C15 C10 C9 120.62(18) . . ?
C15 C10 C11 118.84(18) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.1(2) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.9(2) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.4 . . ?
C13 C14 C15 121.2(2) . . ?
C15 C14 H14 119.4 . . ?
C10 C15 C16 122.87(18) . . ?
C14 C15 C10 118.91(19) . . ?
C14 C15 C16 118.22(19) . . ?
C17 C16 C15 122.12(18) . . ?
C21 C16 C15 121.35(18) . . ?
C21 C16 C17 116.49(19) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 C16 122.00(19) . . ?
C18 C17 H17 119.0 . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.12(19) . . ?
C19 C18 H18 119.4 . . ?
N2 C19 C18 121.59(18) . . ?
N2 C19 C20 121.50(18) . . ?
C18 C19 C20 116.90(19) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.90(19) . . ?
C21 C20 H20 119.6 . . ?
C16 C21 H21 118.7 . . ?
C20 C21 C16 122.54(19) . . ?
C20 C21 H21 118.7 . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23B 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
S1 C1 C2 C3 179.80(17) . . . . ?
S1 C1 C6 N1 -0.6(2) . . . . ?
S1 C1 C6 C5 179.43(16) . . . . ?
S1 C7 C8 C9 9.0(3) . . . . ?
N1 C7 C8 C9 -172.9(2) . . . . ?
N2 C19 C20 C21 -177.00(18) . . . . ?
C1 S1 C7 N1 -0.68(16) . . . . ?
C1 S1 C7 C8 177.58(17) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C1 C6 N1 178.30(18) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 N1 -178.7(2) . . . . ?
C4 C5 C6 C1 1.4(3) . . . . ?
C6 N1 C7 S1 0.5(2) . . . . ?
C6 N1 C7 C8 -177.69(18) . . . . ?
C6 C1 C2 C3 1.2(3) . . . . ?
C7 S1 C1 C2 -178.1(2) . . . . ?
C7 S1 C1 C6 0.65(16) . . . . ?
C7 N1 C6 C1 0.1(2) . . . . ?
C7 N1 C6 C5 -179.9(2) . . . . ?
C7 C8 C9 C10 -177.84(19) . . . . ?
C8 C9 C10 C11 -5.9(3) . . . . ?
C8 C9 C10 C15 175.6(2) . . . . ?
C9 C10 C11 C12 -177.63(19) . . . . ?
C9 C10 C15 C14 177.88(17) . . . . ?
C9 C10 C15 C16 -1.5(3) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C10 C15 C16 C17 -61.0(3) . . . . ?
C10 C15 C16 C21 121.3(2) . . . . ?
C11 C10 C15 C14 -0.7(3) . . . . ?
C11 C10 C15 C16 179.95(17) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C10 0.0(3) . . . . ?
C13 C14 C15 C16 179.37(18) . . . . ?
C14 C15 C16 C17 119.6(2) . . . . ?
C14 C15 C16 C21 -58.1(2) . . . . ?
C15 C10 C11 C12 0.9(3) . . . . ?
C15 C16 C17 C18 -175.59(18) . . . . ?
C15 C16 C21 C20 177.02(18) . . . . ?
C16 C17 C18 C19 -1.5(3) . . . . ?
C17 C16 C21 C20 -0.8(3) . . . . ?
C17 C18 C19 N2 178.38(18) . . . . ?
C17 C18 C19 C20 -0.8(3) . . . . ?
C18 C19 C20 C21 2.2(3) . . . . ?
C19 C20 C21 C16 -1.4(3) . . . . ?
C21 C16 C17 C18 2.2(3) . . . . ?
C22 N2 C19 C18 -176.42(18) . . . . ?
C22 N2 C19 C20 2.7(3) . . . . ?
C23 N2 C19 C18 -7.9(3) . . . . ?
C23 N2 C19 C20 171.24(18) . . . . ?

_exptl_crystal_preparation       Luminescent
