# Electronic Supplementary Material (ESI) for Soft Matter.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1919360'
loop_
_audit_author_name
_audit_author_address
'XING pengyao'
;Shandong University
China
;
_audit_update_record             
;
2019-05-29 deposited with the CCDC.	2019-07-19 downloaded from the CCDC.
;
_audit_creation_date             2019-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C17 H15 N O4), C10 H8 N2'
_chemical_formula_sum            'C44 H38 N4 O8'
_chemical_formula_weight         750.78
_chemical_melting_point          ?
_chemical_oxdiff_formula         CNO
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   46.5364(17)
_cell_length_b                   4.8799(2)
_cell_length_c                   16.5283(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.576(4)
_cell_angle_gamma                90
_cell_volume                     3689.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4452
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      74.8160
_cell_measurement_theta_min      3.8130
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1576
_exptl_crystal_size_max          0.015
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_h_min       -54
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8998
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.035
_diffrn_reflns_theta_min         3.865
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -123.00 -34.00   1.00    0.70    --  -48.45 -12.00 -45.00   89
  2  ω    -42.00  26.00   1.00    0.70    --  -48.45  12.00 126.00   68
  3  ω     49.00  97.00   1.00    0.70    --   48.45  12.00 126.00   48
  4  ω      5.00  57.00   1.00    0.70    --   48.45 -12.00 -45.00   52
  5  ω   -133.00 -92.00   1.00    4.50    --  -86.25 -12.00 -45.00   41
  6  ω    -81.00 -56.00   1.00    4.50    --  -86.25  12.00 126.00   25
  7  ω     73.00  99.00   1.00    4.50    --  106.49 -12.00 -45.00   26
  8  ω     91.00 172.00   1.00    4.50    --  106.49  12.00 126.00   81
  9  ω     43.00  92.00   1.00    0.70    --   48.45-125.00-120.00   49
 10  ω     32.00 119.00   1.00    4.50    --  106.49 -30.00 -60.00   87
 11  ω     56.00 129.00   1.00    4.50    --  106.49 -77.00  30.00   73
 12  ω     38.00  91.00   1.00    4.50    --  106.49 -94.00 -30.00   53
 13  ω     58.00 108.00   1.00    4.50    --  106.49 -94.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0780712000
_diffrn_orient_matrix_UB_12      -0.0429824000
_diffrn_orient_matrix_UB_13      0.0230158000
_diffrn_orient_matrix_UB_21      0.0509454000
_diffrn_orient_matrix_UB_22      -0.0343349000
_diffrn_orient_matrix_UB_23      -0.0245917000
_diffrn_orient_matrix_UB_31      0.0163942000
_diffrn_orient_matrix_UB_32      0.3107145000
_diffrn_orient_matrix_UB_33      0.0004429000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2672
_reflns_number_total             3229
_reflns_odcompleteness_completeness 98.68
_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 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (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    ?
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0723
_refine_ls_restrained_S_all      1.126
_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)+(0.0438P)²+17.4454P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1897
_refine_ls_wR_factor_ref         0.2012
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C8(H8), C12(H12), C14(H14), C22(H22)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.10802(6) 0.4415(6) 0.05420(16) 0.0496(7) Uani 1 1 d . . . . .
O2 O 0.10952(7) 0.1380(5) 0.15885(17) 0.0575(8) Uani 1 1 d . . . . .
O3 O 0.07821(8) 0.3056(9) 0.35728(18) 0.0809(11) Uani 1 1 d . . . . .
H3 H 0.0677 0.1811 0.3683 0.121 Uiso 1 1 calc GR . . . .
O4 O 0.05072(7) 0.2717(8) 0.23338(17) 0.0715(10) Uani 1 1 d . . . . .
N1 N 0.09423(7) 0.5740(7) 0.1682(2) 0.0498(8) Uani 1 1 d . . . . .
H1 H 0.0878 0.7195 0.1416 0.060 Uiso 1 1 calc R . . . .
C1 C 0.10433(8) 0.3660(8) 0.1299(2) 0.0436(9) Uani 1 1 d . . . . .
C2 C 0.07162(9) 0.3607(9) 0.2784(2) 0.0484(9) Uani 1 1 d . . . . .
C3 C 0.16512(8) 0.1662(8) -0.0594(2) 0.0459(9) Uani 1 1 d . . . . .
C4 C 0.14971(8) 0.3692(8) -0.0132(2) 0.0456(9) Uani 1 1 d . . . . .
H4 H 0.1448 0.5342 -0.0467 0.055 Uiso 1 1 calc R . . . .
C6 C 0.15500(9) 0.0278(9) -0.1322(3) 0.0541(10) Uani 1 1 d . . . . .
H6 H 0.1360 0.0563 -0.1606 0.065 Uiso 1 1 calc R . . . .
C7 C 0.12175(9) 0.2442(9) 0.0072(3) 0.0513(10) Uani 1 1 d . . . . .
H7A H 0.1084 0.1975 -0.0432 0.062 Uiso 1 1 calc R . . . .
H7B H 0.1264 0.0779 0.0391 0.062 Uiso 1 1 calc R . . . .
C9 C 0.19347(9) 0.1192(9) -0.0164(3) 0.0504(10) Uani 1 1 d . . . . .
C10 C 0.17315(9) 0.4373(8) 0.0613(2) 0.0482(9) Uani 1 1 d . . . . .
C11 C 0.09421(10) 0.5524(9) 0.2558(2) 0.0517(10) Uani 1 1 d . . . . .
H11A H 0.0910 0.7334 0.2767 0.062 Uiso 1 1 calc R . . . .
H11B H 0.1134 0.4913 0.2831 0.062 Uiso 1 1 calc R . . . .
C13 C 0.19846(9) 0.2894(9) 0.0577(3) 0.0509(10) Uani 1 1 d . . . . .
C15 C 0.17270(10) 0.6199(9) 0.1251(3) 0.0596(11) Uani 1 1 d . . . . .
H15 H 0.1558 0.7191 0.1280 0.071 Uiso 1 1 calc R . . . .
C16 C 0.17335(11) -0.1535(10) -0.1624(3) 0.0618(12) Uani 1 1 d . . . . .
H16 H 0.1667 -0.2468 -0.2113 0.074 Uiso 1 1 calc R . . . .
C17 C 0.19753(11) 0.6536(11) 0.1847(3) 0.0675(13) Uani 1 1 d . . . . .
H17 H 0.1974 0.7773 0.2274 0.081 Uiso 1 1 calc R . . . .
C18 C 0.22323(10) 0.3220(11) 0.1179(3) 0.0681(13) Uani 1 1 d . . . . .
H18 H 0.2401 0.2218 0.1155 0.082 Uiso 1 1 calc R . . . .
C19 C 0.20159(11) -0.1966(11) -0.1203(3) 0.0700(13) Uani 1 1 d . . . . .
H19 H 0.2138 -0.3176 -0.1414 0.084 Uiso 1 1 calc R . . . .
C20 C 0.21184(10) -0.0602(11) -0.0467(3) 0.0666(13) Uani 1 1 d . . . . .
H20 H 0.2308 -0.0896 -0.0184 0.080 Uiso 1 1 calc R . . . .
C21 C 0.22263(12) 0.5053(12) 0.1814(3) 0.0744(14) Uani 1 1 d . . . . .
H21 H 0.2391 0.5289 0.2220 0.089 Uiso 1 1 calc R . . . .
N2 N 0.04267(8) -0.0190(9) 0.4132(2) 0.0627(10) Uani 1 1 d . . . . .
C5 C 0.00901(8) -0.4010(9) 0.4818(2) 0.0498(10) Uani 1 1 d . . . . .
C8 C 0.03055(8) -0.2465(10) 0.5295(2) 0.0544(11) Uani 1 1 d . . . . .
H8 H 0.0343 -0.2685 0.5864 0.065 Uiso 1 1 calc R . . . .
C12 C 0.04645(9) -0.0611(10) 0.4937(3) 0.0608(12) Uani 1 1 d . . . . .
H12 H 0.0607 0.0408 0.5277 0.073 Uiso 1 1 calc R . . . .
C14 C 0.00515(12) -0.3592(12) 0.3978(3) 0.0775(16) Uani 1 1 d . . . . .
H14 H -0.0089 -0.4587 0.3624 0.093 Uiso 1 1 calc R . . . .
C22 C 0.02220(12) -0.1695(13) 0.3666(3) 0.0836(17) Uani 1 1 d . . . . .
H22 H 0.0192 -0.1454 0.3099 0.100 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
O1 C1 1.346(4) . ?
O1 C7 1.456(5) . ?
O2 C1 1.217(4) . ?
O3 C2 1.311(5) . ?
O4 C2 1.193(5) . ?
N1 C1 1.327(5) . ?
N1 C11 1.451(5) . ?
C2 C11 1.505(6) . ?
C3 C4 1.510(5) . ?
C3 C6 1.385(6) . ?
C3 C9 1.398(5) . ?
C4 C7 1.530(5) . ?
C4 C10 1.525(6) . ?
C6 C16 1.385(6) . ?
C9 C13 1.463(6) . ?
C9 C20 1.381(6) . ?
C10 C13 1.392(6) . ?
C10 C15 1.384(6) . ?
C13 C18 1.386(6) . ?
C15 C17 1.383(6) . ?
C16 C19 1.386(7) . ?
C17 C21 1.383(7) . ?
C18 C21 1.384(7) . ?
C19 C20 1.392(7) . ?
N2 C12 1.326(5) . ?
N2 C22 1.330(6) . ?
C5 C5 1.479(8) 5_546 ?
C5 C8 1.380(6) . ?
C5 C14 1.381(6) . ?
C8 C12 1.370(6) . ?
C14 C22 1.379(7) . ?

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 O1 C7 117.3(3) . . ?
C1 N1 C11 119.0(3) . . ?
O2 C1 O1 124.4(4) . . ?
O2 C1 N1 125.0(4) . . ?
N1 C1 O1 110.6(3) . . ?
O3 C2 C11 109.1(3) . . ?
O4 C2 O3 124.1(4) . . ?
O4 C2 C11 126.7(4) . . ?
C6 C3 C4 130.0(4) . . ?
C6 C3 C9 120.0(4) . . ?
C9 C3 C4 110.0(4) . . ?
C3 C4 C7 110.6(3) . . ?
C3 C4 C10 102.5(3) . . ?
C10 C4 C7 114.8(3) . . ?
C3 C6 C16 119.4(4) . . ?
O1 C7 C4 109.1(3) . . ?
C3 C9 C13 108.8(3) . . ?
C20 C9 C3 120.6(4) . . ?
C20 C9 C13 130.5(4) . . ?
C13 C10 C4 109.8(4) . . ?
C15 C10 C4 130.3(4) . . ?
C15 C10 C13 119.8(4) . . ?
N1 C11 C2 114.9(3) . . ?
C10 C13 C9 108.9(4) . . ?
C18 C13 C9 130.5(4) . . ?
C18 C13 C10 120.6(4) . . ?
C17 C15 C10 119.4(5) . . ?
C6 C16 C19 120.4(5) . . ?
C15 C17 C21 120.7(5) . . ?
C21 C18 C13 119.2(5) . . ?
C16 C19 C20 120.5(4) . . ?
C9 C20 C19 119.0(4) . . ?
C17 C21 C18 120.2(5) . . ?
C12 N2 C22 116.3(4) . . ?
C8 C5 C5 122.0(4) . 5_546 ?
C8 C5 C14 116.2(4) . . ?
C14 C5 C5 121.8(5) . 5_546 ?
C12 C8 C5 120.4(4) . . ?
N2 C12 C8 123.6(4) . . ?
C22 C14 C5 119.7(5) . . ?
N2 C22 C14 123.7(4) . . ?

_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 1.982
_oxdiff_exptl_absorpt_empirical_full_min 0.690
