# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 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_bwn18122
_database_code_depnum_ccdc_archive 'CCDC 1882581'
loop_
_audit_author_name
_audit_author_address
'shuangxiong dai'
;College of Materials Science and Engineering, Beijing Institute of Technology, 5 South Zhongguancun 
China
;
_audit_update_record             
;
2018-12-02 deposited with the CCDC.	2019-04-01 downloaded from the CCDC.
;
_audit_creation_date             2018-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H46 N2 O4'
_chemical_formula_sum            'C44 H46 N2 O4'
_chemical_formula_weight         666.83
_chemical_melting_point          ?
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'
O O 0.0106 0.0060 '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                   6.3304(13)
_cell_length_b                   7.2037(14)
_cell_length_c                   20.473(4)
_cell_angle_alpha                89.41(3)
_cell_angle_beta                 89.13(3)
_cell_angle_gamma                76.08(3)
_cell_volume                     906.1(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2896
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4700
_cell_measurement_theta_min      1.9898
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12409
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.913
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3766
_reflns_number_total             4138
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0638
_refine_ls_restrained_S_all      1.155
_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)+(0.0492P)²+0.3585P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1476
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C14(H14),
 C15(H15)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.2028(2) 0.2086(2) 0.36076(6) 0.0413(4) Uani 1 1 d . . . . .
O2 O 0.5262(2) 0.2823(2) 0.37004(6) 0.0336(3) Uani 1 1 d . . . . .
N1 N 0.3646(2) 0.52902(19) 0.07431(6) 0.0214(3) Uani 1 1 d . . . . .
C1 C 0.5312(2) 0.4582(2) 0.02991(7) 0.0211(3) Uani 1 1 d . . . . .
C2 C 0.7392(2) 0.3301(2) 0.02387(8) 0.0222(3) Uani 1 1 d . . . . .
H2 H 0.819511 0.253019 0.057299 0.027 Uiso 1 1 calc R . . . .
C3 C 0.1997(3) 0.6589(2) 0.04087(8) 0.0215(3) Uani 1 1 d . . . . .
C4 C 0.0055(3) 0.7714(2) 0.07506(8) 0.0216(3) Uani 1 1 d . . . . .
C5 C -0.1990(3) 0.7989(2) 0.04655(8) 0.0240(3) Uani 1 1 d . . . . .
H5 H -0.211270 0.749157 0.004364 0.029 Uiso 1 1 calc R . . . .
C6 C -0.3842(3) 0.8986(2) 0.07951(9) 0.0279(4) Uani 1 1 d . . . . .
H6 H -0.522706 0.915758 0.059945 0.033 Uiso 1 1 calc R . . . .
C7 C -0.3680(3) 0.9732(2) 0.14074(9) 0.0301(4) Uani 1 1 d . . . . .
H7 H -0.495466 1.038429 0.163648 0.036 Uiso 1 1 calc R . . . .
C8 C -0.1651(3) 0.9525(2) 0.16861(8) 0.0295(4) Uani 1 1 d . . . . .
H8 H -0.153616 1.006369 0.210185 0.035 Uiso 1 1 calc R . . . .
C9 C 0.0205(3) 0.8537(2) 0.13606(8) 0.0269(4) Uani 1 1 d . . . . .
H9 H 0.159027 0.841447 0.155180 0.032 Uiso 1 1 calc R . . . .
C10 C 0.3592(2) 0.4642(2) 0.13995(7) 0.0205(3) Uani 1 1 d . . . . .
C11 C 0.1829(3) 0.3980(2) 0.16358(8) 0.0241(3) Uani 1 1 d . . . . .
H11 H 0.064064 0.396549 0.135980 0.029 Uiso 1 1 calc R . . . .
C12 C 0.1825(3) 0.3344(2) 0.22763(8) 0.0249(4) Uani 1 1 d . . . . .
H12 H 0.062393 0.289527 0.243969 0.030 Uiso 1 1 calc R . . . .
C13 C 0.3566(3) 0.3355(2) 0.26833(8) 0.0236(3) Uani 1 1 d . . . . .
C14 C 0.5329(3) 0.4008(2) 0.24393(8) 0.0247(4) Uani 1 1 d . . . . .
H14 H 0.652818 0.400704 0.271273 0.030 Uiso 1 1 calc R . . . .
C15 C 0.5338(3) 0.4659(2) 0.18005(8) 0.0235(3) Uani 1 1 d . . . . .
H15 H 0.653449 0.511451 0.163716 0.028 Uiso 1 1 calc R . . . .
C16 C 0.3498(3) 0.2675(2) 0.33702(8) 0.0265(4) Uani 1 1 d . . . . .
C17 C 0.5374(3) 0.2220(3) 0.43817(8) 0.0323(4) Uani 1 1 d . . . . .
H17A H 0.553235 0.082138 0.441527 0.039 Uiso 1 1 calc R . . . .
H17B H 0.403187 0.287137 0.462011 0.039 Uiso 1 1 calc R . . . .
C18 C 0.7325(3) 0.2755(3) 0.46653(8) 0.0323(4) Uani 1 1 d . . . . .
H18A H 0.715275 0.415215 0.461680 0.039 Uiso 1 1 calc R . . . .
H18B H 0.864416 0.210814 0.441578 0.039 Uiso 1 1 calc R . . . .
C19 C 0.7635(3) 0.2208(3) 0.53842(8) 0.0315(4) Uani 1 1 d . . . . .
H19A H 0.631512 0.285428 0.563346 0.038 Uiso 1 1 calc R . . . .
H19B H 0.780772 0.081094 0.543247 0.038 Uiso 1 1 calc R . . . .
C20 C 0.9604(3) 0.2748(3) 0.56716(9) 0.0329(4) Uani 1 1 d . . . . .
H20A H 0.943379 0.414245 0.561421 0.040 Uiso 1 1 calc R . . . .
H20B H 1.091805 0.209235 0.542161 0.040 Uiso 1 1 calc R . . . .
C21 C 0.9965(3) 0.2249(3) 0.63930(9) 0.0368(4) Uani 1 1 d . . . . .
H21A H 0.864715 0.288160 0.664576 0.044 Uiso 1 1 calc R . . . .
H21B H 1.018559 0.084965 0.645255 0.044 Uiso 1 1 calc R . . . .
C22 C 1.1913(4) 0.2862(4) 0.66576(11) 0.0539(6) Uani 1 1 d . . . . .
H22A H 1.323943 0.215404 0.643482 0.081 Uiso 1 1 calc GR . . . .
H22B H 1.202521 0.259164 0.712757 0.081 Uiso 1 1 calc GR . . . .
H22C H 1.173289 0.423589 0.658139 0.081 Uiso 1 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
O1 C16 1.206(2) . ?
O2 C16 1.340(2) . ?
O2 C17 1.454(2) . ?
N1 C1 1.386(2) . ?
N1 C3 1.404(2) . ?
N1 C10 1.421(2) . ?
C1 C1 1.380(3) 2_665 ?
C1 C2 1.419(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(2) 2_665 ?
C3 C4 1.471(2) . ?
C4 C5 1.397(2) . ?
C4 C9 1.402(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.393(2) . ?
C10 C15 1.390(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.393(2) . ?
C13 C14 1.395(2) . ?
C13 C16 1.488(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(2) . ?
C15 H15 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.506(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.523(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.520(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.524(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.515(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C16 O2 C17 116.97(14) . . ?
C1 N1 C3 107.71(13) . . ?
C1 N1 C10 124.49(13) . . ?
C3 N1 C10 127.55(13) . . ?
N1 C1 C2 142.75(14) . . ?
C1 C1 N1 107.58(17) 2_665 . ?
C1 C1 C2 109.66(18) 2_665 . ?
C1 C2 H2 127.2 . . ?
C3 C2 C1 105.52(14) 2_665 . ?
C3 C2 H2 127.2 2_665 . ?
N1 C3 C4 121.67(14) . . ?
C2 C3 N1 109.53(14) 2_665 . ?
C2 C3 C4 128.61(14) 2_665 . ?
C5 C4 C3 119.95(14) . . ?
C5 C4 C9 118.70(15) . . ?
C9 C4 C3 121.35(14) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.37(15) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.32(16) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.85(16) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.23(16) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 H9 119.8 . . ?
C8 C9 C4 120.44(16) . . ?
C8 C9 H9 119.8 . . ?
C11 C10 N1 120.62(14) . . ?
C15 C10 N1 118.89(14) . . ?
C15 C10 C11 120.49(15) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.44(15) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.61(15) . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 119.39(15) . . ?
C12 C13 C16 119.16(15) . . ?
C14 C13 C16 121.46(15) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.34(15) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 120.1 . . ?
C14 C15 C10 119.74(15) . . ?
C14 C15 H15 120.1 . . ?
O1 C16 O2 123.72(16) . . ?
O1 C16 C13 124.49(16) . . ?
O2 C16 C13 111.78(14) . . ?
O2 C17 H17A 110.3 . . ?
O2 C17 H17B 110.3 . . ?
O2 C17 C18 106.91(14) . . ?
H17A C17 H17B 108.6 . . ?
C18 C17 H17A 110.3 . . ?
C18 C17 H17B 110.3 . . ?
C17 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
C17 C18 C19 112.54(15) . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C18 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 C18 112.63(15) . . ?
C20 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C19 C20 H20A 108.6 . . ?
C19 C20 H20B 108.6 . . ?
C19 C20 C21 114.50(16) . . ?
H20A C20 H20B 107.6 . . ?
C21 C20 H20A 108.6 . . ?
C21 C20 H20B 108.6 . . ?
C20 C21 H21A 109.2 . . ?
C20 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 C20 112.25(17) . . ?
C22 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
O2 C17 C18 C19 179.76(15) . . . . ?
N1 C1 C2 C3 179.5(2) . . . 2_665 ?
N1 C3 C4 C5 -139.27(16) . . . . ?
N1 C3 C4 C9 41.1(2) . . . . ?
N1 C10 C11 C12 179.52(14) . . . . ?
N1 C10 C15 C14 -179.12(14) . . . . ?
C1 N1 C3 C2 0.13(18) . . . 2_665 ?
C1 N1 C3 C4 -175.28(14) . . . . ?
C1 N1 C10 C11 -124.47(17) . . . . ?
C1 N1 C10 C15 54.8(2) . . . . ?
C1 C1 C2 C3 0.7(2) 2_665 . . 2_665 ?
C2 C3 C4 C5 46.3(2) 2_665 . . . ?
C2 C3 C4 C9 -133.34(18) 2_665 . . . ?
C3 N1 C1 C1 -0.6(2) . . . 2_665 ?
C3 N1 C1 C2 -179.4(2) . . . . ?
C3 N1 C10 C11 49.0(2) . . . . ?
C3 N1 C10 C15 -131.71(17) . . . . ?
C3 C4 C5 C6 177.53(15) . . . . ?
C3 C4 C9 C8 -177.41(15) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C5 C4 C9 C8 3.0(2) . . . . ?
C5 C6 C7 C8 1.7(3) . . . . ?
C6 C7 C8 C9 -1.5(3) . . . . ?
C7 C8 C9 C4 -0.8(3) . . . . ?
C9 C4 C5 C6 -2.8(2) . . . . ?
C10 N1 C1 C1 174.04(16) . . . 2_665 ?
C10 N1 C1 C2 -4.8(3) . . . . ?
C10 N1 C3 C2 -174.24(14) . . . 2_665 ?
C10 N1 C3 C4 10.3(2) . . . . ?
C10 C11 C12 C13 -0.2(2) . . . . ?
C11 C10 C15 C14 0.1(2) . . . . ?
C11 C12 C13 C14 -0.2(2) . . . . ?
C11 C12 C13 C16 179.50(15) . . . . ?
C12 C13 C14 C15 0.7(2) . . . . ?
C12 C13 C16 O1 0.7(3) . . . . ?
C12 C13 C16 O2 -178.38(14) . . . . ?
C13 C14 C15 C10 -0.6(2) . . . . ?
C14 C13 C16 O1 -179.61(17) . . . . ?
C14 C13 C16 O2 1.4(2) . . . . ?
C15 C10 C11 C12 0.3(2) . . . . ?
C16 O2 C17 C18 -172.84(15) . . . . ?
C16 C13 C14 C15 -179.07(15) . . . . ?
C17 O2 C16 O1 0.3(3) . . . . ?
C17 O2 C16 C13 179.39(14) . . . . ?
C17 C18 C19 C20 -179.96(16) . . . . ?
C18 C19 C20 C21 179.33(16) . . . . ?
C19 C20 C21 C22 -178.59(18) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
