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

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

data_19031103
_database_code_depnum_ccdc_archive 'CCDC 1904135'
loop_
_audit_author_name
_audit_author_address
'Xiaoshuang Ma'
;South China university of Technology
China
;
_audit_update_record             
;
2019-03-19 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;
_audit_creation_date             2019-03-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H20'
_chemical_formula_sum            'C32 H20'
_chemical_formula_weight         404.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         CH
_chemical_oxdiff_usercomment     Max190311
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'

_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                   6.13910(10)
_cell_length_b                   15.1547(2)
_cell_length_c                   11.9272(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.6300(10)
_cell_angle_gamma                90
_cell_volume                     1106.04(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2802
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.1910
_cell_measurement_theta_min      4.6980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.523
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear red'
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4204
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.088
_diffrn_reflns_theta_min         4.728
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -91.00  -6.00   1.00    1.00    --  -41.14 125.00-150.00   85
  2  ω   -108.00 -20.00   1.00    1.00    --  -41.14 -38.00  60.00   88
  3  ω     -4.00  23.00   1.00    1.00    --  -41.14  57.00 -60.00   27
  4  ω    -68.00 -42.00   1.00    1.00    --  -41.14  57.00 -60.00   26
  5  ω    101.00 177.00   1.00    1.00    --  106.22 125.00 -30.00   76
  6  ω    126.00 175.00   1.00    1.00    --  106.22 125.00 -90.00   49
  7  ω     33.00 105.00   1.00    1.00    --  106.22 -45.00 -90.00   72
  8  ω    110.00 137.00   1.00    1.00    --  106.22  85.00-164.00   27
  9  ω     25.00  94.00   1.00    1.00    --  106.22 -94.00  60.00   69
 10  ω     59.00 178.00   1.00    1.00    --  106.22  15.00-180.00  119
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1147057000
_diffrn_orient_matrix_UB_12      -0.0645591000
_diffrn_orient_matrix_UB_13      -0.0758090000
_diffrn_orient_matrix_UB_21      0.1972560000
_diffrn_orient_matrix_UB_22      0.0628957000
_diffrn_orient_matrix_UB_23      0.0006932000
_diffrn_orient_matrix_UB_31      0.1065797000
_diffrn_orient_matrix_UB_32      -0.0469593000
_diffrn_orient_matrix_UB_33      0.1050862000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1933
_reflns_number_total             2164
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.090
_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     145
_refine_ls_number_reflns         2164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0558
_refine_ls_restrained_S_all      1.040
_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)+(0.0959P)²+0.0891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1413
_refine_ls_wR_factor_ref         0.1479
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H007), C12(H008), C6(H009), C9(H00A), C16(H00B), C7(H00C), C8(H00D),
 C15(H00E), C14(H00F), C13(H00G)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
C001 C 0.92312(19) 0.52151(8) 0.51666(9) 0.0267(3) Uani 1 1 d . . . . .
C002 C 0.59879(18) 0.60358(8) 0.46992(9) 0.0261(3) Uani 1 1 d . . . . .
C003 C 0.46839(19) 0.63100(8) 0.39729(10) 0.0273(3) Uani 1 1 d . . . . .
C004 C 0.75162(18) 0.56671(8) 0.55255(10) 0.0247(3) Uani 1 1 d . . . . .
C005 C 0.71984(19) 0.57516(8) 0.67339(10) 0.0257(3) Uani 1 1 d . . . . .
C006 C 0.31151(19) 0.65933(8) 0.30993(10) 0.0262(3) Uani 1 1 d . . . . .
C007 C 0.10511(19) 0.68886(8) 0.33479(10) 0.0289(3) Uani 1 1 d . . . . .
H007 H 0.0692 0.6900 0.4090 0.035 Uiso 1 1 calc R . . . .
C008 C 0.8879(2) 0.55324(9) 0.75418(11) 0.0316(3) Uani 1 1 d . . . . .
H008 H 1.0207 0.5330 0.7319 0.038 Uiso 1 1 calc R . . . .
C009 C 0.3612(2) 0.65677(9) 0.19705(10) 0.0319(3) Uani 1 1 d . . . . .
H009 H 0.4971 0.6365 0.1790 0.038 Uiso 1 1 calc R . . . .
C00A C -0.0461(2) 0.71639(9) 0.24972(11) 0.0335(3) Uani 1 1 d . . . . .
H00A H -0.1825 0.7364 0.2671 0.040 Uiso 1 1 calc R . . . .
C00B C 0.5209(2) 0.60487(9) 0.70782(11) 0.0314(3) Uani 1 1 d . . . . .
H00B H 0.4082 0.6200 0.6545 0.038 Uiso 1 1 calc R . . . .
C00C C 0.2090(2) 0.68418(10) 0.11300(10) 0.0377(3) Uani 1 1 d . . . . .
H00C H 0.2431 0.6826 0.0385 0.045 Uiso 1 1 calc R . . . .
C00D C 0.0052(2) 0.71421(9) 0.13860(11) 0.0366(3) Uani 1 1 d . . . . .
H00D H -0.0966 0.7328 0.0815 0.044 Uiso 1 1 calc R . . . .
C00E C 0.4908(2) 0.61181(10) 0.82170(11) 0.0405(4) Uani 1 1 d . . . . .
H00E H 0.3573 0.6309 0.8445 0.049 Uiso 1 1 calc R . . . .
C00F C 0.6587(3) 0.59034(11) 0.90125(11) 0.0434(4) Uani 1 1 d . . . . .
H00F H 0.6383 0.5952 0.9774 0.052 Uiso 1 1 calc R . . . .
C00G C 0.8576(2) 0.56155(10) 0.86743(11) 0.0397(4) Uani 1 1 d . . . . .
H00G H 0.9710 0.5478 0.9210 0.048 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
C001 C001 1.239(2) 3_766 ?
C001 C004 1.3541(16) . ?
C002 C003 1.2049(17) . ?
C002 C004 1.4194(15) . ?
C003 C006 1.4268(16) . ?
C004 C005 1.4755(16) . ?
C005 C008 1.3939(17) . ?
C005 C00B 1.3943(17) . ?
C006 C007 1.3980(16) . ?
C006 C009 1.4049(17) . ?
C007 H007 0.9300 . ?
C007 C00A 1.3831(17) . ?
C008 H008 0.9300 . ?
C008 C00G 1.3840(19) . ?
C009 H009 0.9300 . ?
C009 C00C 1.3784(17) . ?
C00A H00A 0.9300 . ?
C00A C00D 1.3870(18) . ?
C00B H00B 0.9300 . ?
C00B C00E 1.3895(18) . ?
C00C H00C 0.9300 . ?
C00C C00D 1.3883(19) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00E C00F 1.382(2) . ?
C00F H00F 0.9300 . ?
C00F C00G 1.387(2) . ?
C00G H00G 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
C001 C001 C004 178.51(17) 3_766 . ?
C003 C002 C004 176.88(12) . . ?
C002 C003 C006 177.34(13) . . ?
C001 C004 C002 117.83(10) . . ?
C001 C004 C005 121.35(10) . . ?
C002 C004 C005 120.79(10) . . ?
C008 C005 C004 120.38(11) . . ?
C008 C005 C00B 119.37(11) . . ?
C00B C005 C004 120.25(11) . . ?
C007 C006 C003 120.76(10) . . ?
C007 C006 C009 118.87(11) . . ?
C009 C006 C003 120.37(11) . . ?
C006 C007 H007 119.8 . . ?
C00A C007 C006 120.47(11) . . ?
C00A C007 H007 119.8 . . ?
C005 C008 H008 119.9 . . ?
C00G C008 C005 120.19(12) . . ?
C00G C008 H008 119.9 . . ?
C006 C009 H009 119.9 . . ?
C00C C009 C006 120.12(12) . . ?
C00C C009 H009 119.9 . . ?
C007 C00A H00A 119.9 . . ?
C007 C00A C00D 120.22(12) . . ?
C00D C00A H00A 119.9 . . ?
C005 C00B H00B 120.0 . . ?
C00E C00B C005 120.08(12) . . ?
C00E C00B H00B 120.0 . . ?
C009 C00C H00C 119.7 . . ?
C009 C00C C00D 120.60(12) . . ?
C00D C00C H00C 119.7 . . ?
C00A C00D C00C 119.73(12) . . ?
C00A C00D H00D 120.1 . . ?
C00C C00D H00D 120.1 . . ?
C00B C00E H00E 119.9 . . ?
C00F C00E C00B 120.15(12) . . ?
C00F C00E H00E 119.9 . . ?
C00E C00F H00F 120.0 . . ?
C00E C00F C00G 119.99(12) . . ?
C00G C00F H00F 120.0 . . ?
C008 C00G C00F 120.21(13) . . ?
C008 C00G H00G 119.9 . . ?
C00F C00G H00G 119.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.341
_oxdiff_exptl_absorpt_empirical_full_min 0.592
