# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_lhc-31
_database_code_depnum_ccdc_archive 'CCDC 2202296'
loop_
_audit_author_name
_audit_author_address
'Haichao Liu'
;Jilin University
China
;
_audit_update_record             
;
2022-08-19 deposited with the CCDC.	2023-03-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        (E)-9-styrylanthracene
_chemical_name_common            ?
_chemical_melting_point          403
_chemical_formula_moiety         'C22 H16'
_chemical_formula_sum            'C22 H16'
_chemical_formula_weight         280.35

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.5188(11)
_cell_length_b                   24.379(5)
_cell_length_c                   11.411(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.06(3)
_cell_angle_gamma                90.00
_cell_volume                     1511.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10703
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      27.52

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9890
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13891
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3361
_reflns_number_gt                2310
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1132P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3361
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1825
_refine_ls_wR_factor_gt          0.1634
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7751(3) 0.66486(6) 0.27152(12) 0.0410(4) Uani 1 1 d . . .
C2 C 0.5893(3) 0.69428(6) 0.19309(13) 0.0478(4) Uani 1 1 d . . .
H2 H 0.6062 0.7319 0.1841 0.057 Uiso 1 1 calc R . .
C3 C 0.3887(3) 0.66839(7) 0.13142(14) 0.0538(5) Uani 1 1 d . . .
H3 H 0.2699 0.6886 0.0817 0.065 Uiso 1 1 calc R . .
C4 C 0.3584(4) 0.61113(8) 0.14199(15) 0.0579(5) Uani 1 1 d . . .
H4 H 0.2200 0.5939 0.0995 0.070 Uiso 1 1 calc R . .
C5 C 0.5303(4) 0.58139(7) 0.21377(14) 0.0531(5) Uani 1 1 d . . .
H5 H 0.5094 0.5437 0.2193 0.064 Uiso 1 1 calc R . .
C6 C 0.7430(3) 0.60661(6) 0.28128(13) 0.0436(4) Uani 1 1 d . . .
C7 C 0.9217(3) 0.57625(6) 0.35558(12) 0.0475(4) Uani 1 1 d . . .
H7 H 0.9016 0.5385 0.3605 0.057 Uiso 1 1 calc R . .
C8 C 1.1280(3) 0.60047(6) 0.42230(13) 0.0449(4) Uani 1 1 d . . .
C9 C 1.3131(4) 0.56943(7) 0.49785(14) 0.0560(5) Uani 1 1 d . . .
H9 H 1.2952 0.5316 0.5029 0.067 Uiso 1 1 calc R . .
C10 C 1.5129(4) 0.59378(8) 0.56194(15) 0.0636(5) Uani 1 1 d . . .
H10 H 1.6297 0.5728 0.6110 0.076 Uiso 1 1 calc R . .
C11 C 1.5451(4) 0.65092(8) 0.55481(15) 0.0614(5) Uani 1 1 d . . .
H11 H 1.6840 0.6673 0.5987 0.074 Uiso 1 1 calc R . .
C12 C 1.3752(3) 0.68229(7) 0.48440(14) 0.0516(4) Uani 1 1 d . . .
H12 H 1.3990 0.7200 0.4820 0.062 Uiso 1 1 calc R . .
C13 C 1.1612(3) 0.65882(6) 0.41417(12) 0.0424(4) Uani 1 1 d . . .
C14 C 0.9830(3) 0.69040(6) 0.33920(12) 0.0412(4) Uani 1 1 d . . .
C15 C 1.0234(3) 0.75056(6) 0.33018(13) 0.0468(4) Uani 1 1 d . . .
H15 H 1.1575 0.7617 0.2968 0.056 Uiso 1 1 calc R . .
C16 C 0.8878(3) 0.78900(6) 0.36482(13) 0.0474(4) Uani 1 1 d . . .
H16 H 0.7547 0.7772 0.3982 0.057 Uiso 1 1 calc R . .
C17 C 0.9193(3) 0.84881(6) 0.35774(12) 0.0404(4) Uani 1 1 d . . .
C18 C 1.0939(3) 0.87311(6) 0.29998(14) 0.0473(4) Uani 1 1 d . . .
H18 H 1.1961 0.8512 0.2631 0.057 Uiso 1 1 calc R . .
C19 C 1.1168(3) 0.92955(6) 0.29692(14) 0.0522(4) Uani 1 1 d . . .
H19 H 1.2347 0.9453 0.2583 0.063 Uiso 1 1 calc R . .
C20 C 0.9663(3) 0.96265(6) 0.35067(13) 0.0519(5) Uani 1 1 d . . .
H20 H 0.9823 1.0006 0.3483 0.062 Uiso 1 1 calc R . .
C21 C 0.7931(4) 0.93942(7) 0.40761(14) 0.0546(5) Uani 1 1 d . . .
H21 H 0.6912 0.9617 0.4440 0.066 Uiso 1 1 calc R . .
C22 C 0.7687(3) 0.88298(6) 0.41134(14) 0.0504(4) Uani 1 1 d . . .
H22 H 0.6501 0.8677 0.4502 0.061 Uiso 1 1 calc R . .


_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
C1 C14 1.411(2) . ?
C1 C2 1.430(2) . ?
C1 C6 1.438(2) . ?
C2 C3 1.359(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.414(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.351(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.426(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.395(2) . ?
C7 C8 1.387(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.432(2) . ?
C8 C13 1.439(2) . ?
C9 C10 1.349(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.408(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.359(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.426(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.414(2) . ?
C14 C15 1.490(2) . ?
C15 C16 1.303(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.472(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.391(2) . ?
C17 C22 1.392(2) . ?
C18 C19 1.383(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.376(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.369(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.384(2) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 C1 C2 123.14(13) . . ?
C14 C1 C6 119.53(13) . . ?
C2 C1 C6 117.33(13) . . ?
C3 C2 C1 121.41(15) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 120.81(15) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 120.04(15) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 121.38(15) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 121.81(14) . . ?
C7 C6 C1 119.18(14) . . ?
C5 C6 C1 119.01(14) . . ?
C8 C7 C6 122.21(14) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C9 122.44(15) . . ?
C7 C8 C13 119.16(14) . . ?
C9 C8 C13 118.39(15) . . ?
C10 C9 C8 121.54(16) . . ?
C10 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C9 C10 C11 120.20(16) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.65(17) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 121.64(17) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 122.81(14) . . ?
C14 C13 C8 119.63(14) . . ?
C12 C13 C8 117.56(14) . . ?
C1 C14 C13 120.28(13) . . ?
C1 C14 C15 120.91(13) . . ?
C13 C14 C15 118.78(13) . . ?
C16 C15 C14 125.90(17) . . ?
C16 C15 H15 117.1 . . ?
C14 C15 H15 117.1 . . ?
C15 C16 C17 128.02(17) . . ?
C15 C16 H16 116.0 . . ?
C17 C16 H16 116.0 . . ?
C18 C17 C22 118.01(15) . . ?
C18 C17 C16 123.09(14) . . ?
C22 C17 C16 118.89(15) . . ?
C19 C18 C17 120.64(15) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 120.48(16) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C21 C20 C19 119.64(15) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.39(16) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C17 120.84(17) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?

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
C14 C1 C2 C3 -178.45(15) . . . . ?
C6 C1 C2 C3 0.9(2) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C7 -179.95(16) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C14 C1 C6 C7 -1.5(2) . . . . ?
C2 C1 C6 C7 179.14(14) . . . . ?
C14 C1 C6 C5 179.07(15) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
C5 C6 C7 C8 -179.45(15) . . . . ?
C1 C6 C7 C8 1.1(2) . . . . ?
C6 C7 C8 C9 -179.40(15) . . . . ?
C6 C7 C8 C13 -0.6(2) . . . . ?
C7 C8 C9 C10 179.89(16) . . . . ?
C13 C8 C9 C10 1.1(3) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C10 C11 C12 C13 -0.9(3) . . . . ?
C11 C12 C13 C14 -179.29(16) . . . . ?
C11 C12 C13 C8 1.3(3) . . . . ?
C7 C8 C13 C14 0.4(2) . . . . ?
C9 C8 C13 C14 179.25(14) . . . . ?
C7 C8 C13 C12 179.78(15) . . . . ?
C9 C8 C13 C12 -1.4(2) . . . . ?
C2 C1 C14 C13 -179.35(15) . . . . ?
C6 C1 C14 C13 1.3(2) . . . . ?
C2 C1 C14 C15 -1.4(2) . . . . ?
C6 C1 C14 C15 179.29(15) . . . . ?
C12 C13 C14 C1 179.86(15) . . . . ?
C8 C13 C14 C1 -0.8(2) . . . . ?
C12 C13 C14 C15 1.9(2) . . . . ?
C8 C13 C14 C15 -178.78(15) . . . . ?
C1 C14 C15 C16 66.9(2) . . . . ?
C13 C14 C15 C16 -115.14(19) . . . . ?
C14 C15 C16 C17 -179.87(13) . . . . ?
C15 C16 C17 C18 6.5(2) . . . . ?
C15 C16 C17 C22 -173.31(15) . . . . ?
C22 C17 C18 C19 0.4(2) . . . . ?
C16 C17 C18 C19 -179.47(14) . . . . ?
C17 C18 C19 C20 -0.3(2) . . . . ?
C18 C19 C20 C21 0.1(2) . . . . ?
C19 C20 C21 C22 0.0(2) . . . . ?
C20 C21 C22 C17 0.1(2) . . . . ?
C18 C17 C22 C21 -0.3(2) . . . . ?
C16 C17 C22 C21 179.54(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.970
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.970
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.046
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane and methanol'
_exptl_crystal_preparation       Luminescent
