# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_tx1703
_database_code_depnum_ccdc_archive 'CCDC 2072379'
loop_
_audit_author_name
_audit_author_address
'Li Yao'
;Peking University
China
;
_audit_update_record             
;
2021-03-23 deposited with the CCDC.	2021-05-19 downloaded from the CCDC.
;
_audit_creation_date             2019-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H32 N2 O4'
_chemical_formula_sum            'C32 H32 N2 O4'
_chemical_formula_weight         508.59
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.7923(10)
_cell_length_b                   9.0337(12)
_cell_length_c                   14.831(2)
_cell_angle_alpha                101.002(11)
_cell_angle_beta                 94.467(15)
_cell_angle_gamma                96.830(14)
_cell_volume                     622.44(18)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1579
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.6630
_cell_measurement_theta_min      3.0020
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.841
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             270
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6435
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.973
_diffrn_reflns_theta_min         3.052
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00   5.00   0.50    0.25    --   46.70 -64.00  86.00   58
  2  ω     31.00  63.00   0.50    0.25    --   46.70 -64.00  86.00   64
  3  ω     44.00  89.00   0.50    0.25    --   46.70-125.00 120.00   90
  4  ω     32.00 109.00   0.50    1.50    --  103.25 -94.00  90.00  154
  5  ω     42.00 104.00   0.50    1.50    --  103.25 -94.00   0.00  124
  6  ω     42.00 104.00   0.50    1.50    --  103.25-125.00 -60.00  124
  7  ω     31.00 121.00   0.50    1.50    --  103.25 -64.00  86.00  180
  8  ω     91.00 160.00   0.50    1.50    --  103.25  30.00 150.00  138
  9  ω    130.00 162.00   0.50    1.50    --  103.25  77.00 -90.00   64
 10  ω    128.00 160.00   0.50    1.50    --  103.25  77.00-180.00   64
 11  ω     87.00 167.00   0.50    1.50    --  103.25  64.00-137.00  160
 12  ω     87.00 112.00   0.50    1.50    --  103.25  77.00 -90.00   50
 13  ω     82.00 124.00   0.50    1.50    --  103.25  77.00-180.00   84
 14  ω     29.00 119.00   0.50    0.25    --   46.70  64.00-137.00  180
 15  ω     33.00 105.00   0.50    1.50    --  103.25 -94.00-180.00  144
 16  ω     31.00  82.00   0.50    0.25    --   46.70-125.00 -90.00  102
 17  ω    -64.00  26.00   0.50    0.25    --  -46.70  64.00-137.00  180
 18  ω   -118.00 -29.00   0.50    0.25    --  -46.70 -64.00  86.00  178
 19  ω   -111.00 -29.00   0.50    1.50    --  -99.00  45.00  60.00  164
 20  ω    -64.00 -28.00   0.50    1.50    --  -99.00 125.00   0.00   72
 21  ω    -98.00 -73.00   0.50    1.50    --  -99.00 125.00   0.00   50
 22  ω   -116.00 -26.00   0.50    1.50    --  -99.00  64.00-137.00  180
 23  ω    -53.00 -28.00   0.50    1.50    --  -99.00 125.00-120.00   50
 24  ω   -112.00 -24.00   0.50    1.50    --  -99.00  15.00  60.00  176
 25  ω   -117.00 -66.00   0.50    1.50    --  -99.00 125.00-120.00  102
 26  ω   -168.00 -81.00   0.50    1.50    --  -99.00 -64.00  86.00  174
 27  ω   -118.00 -73.00   0.50    0.25    --  -46.70-125.00-120.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2091278000
_diffrn_orient_matrix_UB_12      0.0437918000
_diffrn_orient_matrix_UB_13      0.0711260000
_diffrn_orient_matrix_UB_21      -0.1819956000
_diffrn_orient_matrix_UB_22      -0.1560288000
_diffrn_orient_matrix_UB_23      -0.0347481000
_diffrn_orient_matrix_UB_31      0.1705724000
_diffrn_orient_matrix_UB_32      -0.0670329000
_diffrn_orient_matrix_UB_33      0.0710804000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1807
_reflns_number_total             2402
_reflns_odcompleteness_completeness 99.01
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2402
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0809
_refine_ls_restrained_S_all      1.060
_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)+(0.1628P)²+0.0675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2237
_refine_ls_wR_factor_ref         0.2426
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C14A-C13 = C14-C13 = C15A-C14A = C15-C14 = C16A-C15A = C16-C15
 1.53 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C14 \\sim C14A \\sim C15A \\sim C15 \\sim C16A \\sim C16: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C14) \\sim Ueq, Uanis(C14A) \\sim Ueq, Uanis(C15A) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C16A) \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Sof(H13C)=Sof(H13D)=Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(C15A)=Sof(H15C)=
 Sof(H15D)=Sof(C16A)=Sof(H16D)=Sof(H16E)=Sof(H16F)=1-FVAR(1)
 Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C15)=Sof(H15A)=Sof(H15B)=
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C13(H13C,H13D), C14(H14A,
 H14B), C15(H15A,H15B), C14A(H14C,H14D), C15A(H15C,H15D)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C7(H7)
5.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C16A(H16D,H16E,H16F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O 0.3309(4) 0.51505(18) 0.60122(12) 0.0439(5) Uani 1 1 d . . . . .
O2 O 1.1317(4) 0.79851(19) 0.75591(13) 0.0465(5) Uani 1 1 d . . . . .
N1 N 0.7314(4) 0.6564(2) 0.67813(14) 0.0365(5) Uani 1 1 d . . . . .
C1 C -0.0244(5) 0.8329(3) 0.37292(17) 0.0374(6) Uani 1 1 d . . . . .
H1 H -0.147576 0.742157 0.357499 0.045 Uiso 1 1 calc R . . . .
C2 C -0.0630(5) 0.9503(3) 0.32711(17) 0.0378(6) Uani 1 1 d . . . . .
H2 H -0.213499 0.938239 0.281601 0.045 Uiso 1 1 calc R . . . .
C3 C 0.1222(5) 1.0863(3) 0.34881(16) 0.0359(6) Uani 1 1 d . . . . .
C4 C 0.3475(5) 1.1077(3) 0.41639(16) 0.0351(6) Uani 1 1 d . . . . .
C5 C 0.3881(5) 0.9890(3) 0.46479(16) 0.0347(6) Uani 1 1 d . . . . .
C6 C 0.1991(5) 0.8505(2) 0.44222(16) 0.0344(6) Uani 1 1 d . . . . .
C7 C 0.2434(5) 0.7331(3) 0.49318(17) 0.0367(6) Uani 1 1 d . . . . .
H7 H 0.121649 0.641773 0.479567 0.044 Uiso 1 1 calc R . . . .
C8 C 0.4603(5) 0.7539(3) 0.56073(16) 0.0352(6) Uani 1 1 d . . . . .
C9 C 0.4968(5) 0.6320(2) 0.61384(17) 0.0362(6) Uani 1 1 d . . . . .
C10 C 0.9289(5) 0.7882(3) 0.69998(17) 0.0381(6) Uani 1 1 d . . . . .
C11 C 0.7746(5) 0.5388(3) 0.73284(17) 0.0383(6) Uani 1 1 d . . . . .
H11A H 0.974459 0.530061 0.740658 0.046 Uiso 1 1 calc R . . . .
H11B H 0.676368 0.441314 0.699491 0.046 Uiso 1 1 calc R . . . .
C12 C 0.6677(6) 0.5764(3) 0.82703(18) 0.0437(6) Uani 1 1 d . . . . .
H12A H 0.463271 0.568741 0.819301 0.052 Uiso 1 1 calc R . . . .
H12B H 0.741911 0.680730 0.856050 0.052 Uiso 1 1 calc R . . . .
C13 C 0.7531(6) 0.4714(3) 0.88990(19) 0.0499(7) Uani 1 1 d D . . . .
H13A H 0.957852 0.484168 0.898825 0.060 Uiso 0.759(8) 1 calc R . P A 1
H13B H 0.688046 0.506183 0.949633 0.060 Uiso 0.759(8) 1 calc R . P A 1
H13C H 0.726045 0.513850 0.953282 0.060 Uiso 0.241(8) 1 calc R . P A 2
H13D H 0.950792 0.459261 0.886953 0.060 Uiso 0.241(8) 1 calc R . P A 2
C14 C 0.6512(14) 0.3042(5) 0.8605(4) 0.0522(15) Uani 0.759(8) 1 d D U P A 1
H14A H 0.723836 0.265455 0.802635 0.063 Uiso 0.759(8) 1 calc R . P A 1
H14B H 0.446584 0.288709 0.850043 0.063 Uiso 0.759(8) 1 calc R . P A 1
C15 C 0.7438(12) 0.2153(5) 0.9320(3) 0.0572(12) Uani 0.759(8) 1 d D U P A 1
H15A H 0.947615 0.236234 0.945300 0.069 Uiso 0.759(8) 1 calc R . P A 1
H15B H 0.661415 0.249987 0.988635 0.069 Uiso 0.759(8) 1 calc R . P A 1
C16 C 0.6582(13) 0.0456(5) 0.9007(3) 0.0716(15) Uani 0.759(8) 1 d D U P A 1
H16A H 0.738941 0.010485 0.844600 0.107 Uiso 0.759(8) 1 calc GR . P A 1
H16B H 0.456051 0.023645 0.890100 0.107 Uiso 0.759(8) 1 calc GR . P A 1
H16C H 0.725421 -0.005301 0.947670 0.107 Uiso 0.759(8) 1 calc GR . P A 1
C14A C 0.566(4) 0.3157(14) 0.8569(14) 0.053(5) Uani 0.241(8) 1 d D U P A 2
H14C H 0.373910 0.336486 0.845733 0.063 Uiso 0.241(8) 1 calc R . P A 2
H14D H 0.622538 0.270931 0.797457 0.063 Uiso 0.241(8) 1 calc R . P A 2
C15A C 0.556(3) 0.1923(13) 0.9149(10) 0.054(3) Uani 0.241(8) 1 d D U P A 2
H15C H 0.498275 0.232861 0.975003 0.064 Uiso 0.241(8) 1 calc R . P A 2
H15D H 0.415191 0.107245 0.884952 0.064 Uiso 0.241(8) 1 calc R . P A 2
C16A C 0.841(3) 0.136(2) 0.9276(11) 0.070(4) Uani 0.241(8) 1 d D U P A 2
H16D H 0.885648 0.082614 0.869239 0.106 Uiso 0.241(8) 1 calc GR . P A 2
H16E H 0.833326 0.068968 0.970549 0.106 Uiso 0.241(8) 1 calc GR . P A 2
H16F H 0.984520 0.221563 0.950967 0.106 Uiso 0.241(8) 1 calc GR . 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
O1 C9 1.219(3) . ?
O2 C10 1.210(3) . ?
N1 C9 1.384(3) . ?
N1 C10 1.399(3) . ?
N1 C11 1.478(3) . ?
C1 C2 1.386(3) . ?
C1 C6 1.398(4) . ?
C2 C3 1.396(4) . ?
C3 C4 1.384(4) . ?
C3 C10 1.490(3) 2_676 ?
C4 C5 1.423(3) . ?
C4 C8 1.429(4) 2_676 ?
C5 C5 1.405(5) 2_676 ?
C5 C6 1.422(3) . ?
C6 C7 1.441(3) . ?
C7 C8 1.356(4) . ?
C8 C9 1.489(3) . ?
C11 C12 1.517(4) . ?
C12 C13 1.520(3) . ?
C13 C14 1.500(5) . ?
C13 C14A 1.545(10) . ?
C14 C15 1.516(6) . ?
C15 C16 1.512(5) . ?
C14A C15A 1.531(10) . ?
C15A C16A 1.526(10) . ?

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
C9 N1 C10 125.46(19) . . ?
C9 N1 C11 118.67(19) . . ?
C10 N1 C11 115.79(19) . . ?
C2 C1 C6 120.2(2) . . ?
C1 C2 C3 120.5(2) . . ?
C2 C3 C10 119.2(2) . 2_676 ?
C4 C3 C2 121.1(2) . . ?
C4 C3 C10 119.7(2) . 2_676 ?
C3 C4 C5 119.2(2) . . ?
C3 C4 C8 121.8(2) . 2_676 ?
C5 C4 C8 119.1(2) . 2_676 ?
C5 C5 C4 119.6(3) 2_676 . ?
C5 C5 C6 120.8(3) 2_676 . ?
C6 C5 C4 119.5(2) . . ?
C1 C6 C5 119.6(2) . . ?
C1 C6 C7 122.2(2) . . ?
C5 C6 C7 118.3(2) . . ?
C8 C7 C6 120.9(2) . . ?
C4 C8 C9 119.0(2) 2_676 . ?
C7 C8 C4 121.3(2) . 2_676 ?
C7 C8 C9 119.7(2) . . ?
O1 C9 N1 121.0(2) . . ?
O1 C9 C8 122.1(2) . . ?
N1 C9 C8 116.9(2) . . ?
O2 C10 N1 121.0(2) . . ?
O2 C10 C3 122.1(2) . 2_676 ?
N1 C10 C3 116.9(2) . 2_676 ?
N1 C11 C12 111.81(18) . . ?
C11 C12 C13 112.5(2) . . ?
C12 C13 C14A 107.9(6) . . ?
C14 C13 C12 118.4(3) . . ?
C13 C14 C15 112.2(4) . . ?
C16 C15 C14 112.8(4) . . ?
C15A C14A C13 121.9(12) . . ?
C16A C15A C14A 111.8(13) . . ?

_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 3.115
_oxdiff_exptl_absorpt_empirical_full_min 0.425
