# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_xiao201_zql1_0m
_database_code_depnum_ccdc_archive 'CCDC 2048337'
loop_
_audit_author_name
_audit_author_address
'Wen Nian Jiang'
;Central South University
China
;
_audit_update_record             
;
2020-12-04 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;
_audit_creation_date             2019-02-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         '4(C19 H17 N O)'
_chemical_formula_sum            'C76 H68 N4 O4'
_chemical_formula_weight         1101.41
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/a 1'
_space_group_name_Hall           '-P 2ybc (z,y,-x)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z
3 -x,-y,-z
4 x-1/2,-y-1/2,z

_symmetry_Int_Tables_number      14
_cell_length_a                   8.5293(5)
_cell_length_b                   15.1500(9)
_cell_length_c                   11.6254(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.4953(18)
_cell_angle_gamma                90
_cell_volume                     1497.60(15)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5291
_cell_measurement_theta_max      22.649
_cell_measurement_theta_min      3.159
_cell_measurement_temperature    296(2)
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0697 before and 0.0596 after correction.
The Ratio of minimum to maximum transmission is 0.9340.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.2211
_exptl_crystal_F_000             584.2480
_exptl_crystal_size_max          0.323
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.051
_exptl_crystal_description       BAR
_exptl_crystal_colour            COLORLESS
_diffrn_ambient_temperature      296(2)
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23562
_diffrn_reflns_theta_full        27.5668
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         3.16
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.9977
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71076
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              0
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              -15
_reflns_number_gt                1922
_reflns_number_total             3456
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.4225
_refine_diff_density_min         -0.4317
_refine_diff_density_rms         0.1147
_refine_ls_d_res_high            0.7679
_refine_ls_d_res_low             6.4493
_refine_ls_goodness_of_fit_ref   1.0664
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3456
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1342
_refine_ls_R_factor_gt           0.0646
_refine_ls_restrained_S_all      1.0664
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0681P)²+0.1131P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1226
_refine_ls_wR_factor_ref         0.1502
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C13(H13), C14(H14), C15(H15), C16(H16), C3(H3), C2(H2),
 C1(H1), C6(H6), C5(H5)
2.b Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c), C18(H18a,H18b,H18c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
C10 C 0.15262(19) 0.38419(11) 0.97378(15) 0.0384(4) Uani 1.000000 .
C11 C 0.17423(19) 0.39129(11) 0.85389(15) 0.0389(4) Uani 1.000000 .
C4 C 0.2362(2) 0.56386(12) 0.62908(14) 0.0414(5) Uani 1.000000 .
C12 C 0.2804(2) 0.47990(13) 0.68973(16) 0.0467(5) Uani 1.000000 .
C5 C 0.1128(2) 0.61586(12) 0.66052(17) 0.0514(5) Uani 1.000000 .
C7 C 0.2445(2) 0.46950(12) 0.81228(15) 0.0419(5) Uani 1.000000 .
C3 C 0.3148(2) 0.58902(13) 0.53412(16) 0.0516(5) Uani 1.000000 .
C9 C 0.2735(2) 0.52663(13) 1.00738(16) 0.0516(5) Uani 1.000000 .
C8 C 0.2848(2) 0.53580(13) 0.88871(16) 0.0522(5) Uani 1.000000 .
C2 C 0.2713(3) 0.66398(15) 0.47341(17) 0.0595(6) Uani 1.000000 .
C1 C 0.1494(3) 0.71468(14) 0.50537(17) 0.0615(6) Uani 1.000000 .
C6 C 0.0701(3) 0.69052(14) 0.59851(19) 0.0627(6) Uani 1.000000 .
O1 O 0.34632(19) 0.42131(9) 0.63966(12) 0.0705(5) Uani 1.000000 .
C17 C 0.21387(19) 0.45132(12) 1.05172(15) 0.0412(4) Uani 1.000000 .
C19 C 0.2244(3) 0.51675(16) 1.24349(17) 0.0723(7) Uani 1.000000 .
C13 C 0.0649(2) 0.31185(12) 1.01100(17) 0.0496(5) Uani 1.000000 .
N1 N 0.20488(18) 0.43849(11) 1.17088(13) 0.0512(4) Uani 1.000000 .
C14 C 0.0086(2) 0.24831(13) 0.93649(18) 0.0586(6) Uani 1.000000 .
C16 C 0.1150(2) 0.32303(12) 0.77961(16) 0.0485(5) Uani 1.000000 .
C15 C 0.0352(2) 0.25350(13) 0.81975(18) 0.0572(6) Uani 1.000000 .
C18 C 0.2978(3) 0.36520(16) 1.22091(18) 0.0696(7) Uani 1.000000 .
H9 H 0.3070(2) 0.57233(13) 1.05678(16) 0.0619(6) Uiso 1.000000 R
H8 H 0.3211(2) 0.58892(13) 0.86072(16) 0.0627(6) Uiso 1.000000 R
H13 H 0.0453(2) 0.30769(12) 1.08839(17) 0.0595(6) Uiso 1.000000 R
H14 H -0.0480(2) 0.20112(13) 0.96333(18) 0.0703(7) Uiso 1.000000 R
H15 H -0.0018(2) 0.20918(13) 0.76936(18) 0.0687(7) Uiso 1.000000 R
H16 H 0.1311(2) 0.32590(12) 0.70150(16) 0.0581(6) Uiso 1.000000 R
H3 H 0.3975(2) 0.55480(13) 0.51147(16) 0.0619(6) Uiso 1.000000 R
H2 H 0.3251(3) 0.68038(15) 0.41021(17) 0.0714(7) Uiso 1.000000 R
H1 H 0.1203(3) 0.76542(14) 0.46400(17) 0.0738(7) Uiso 1.000000 R
H6 H -0.0132(3) 0.72487(14) 0.61993(19) 0.0752(7) Uiso 1.000000 R
H5 H 0.0587(2) 0.60018(12) 0.72384(17) 0.0617(6) Uiso 1.000000 R
H19a H 0.3325(4) 0.5351(6) 1.2480(11) 0.1084(11) Uiso 1.000000 GR
H19b H 0.1590(13) 0.5634(3) 1.2108(7) 0.1084(11) Uiso 1.000000 GR
H19c H 0.1947(17) 0.5033(3) 1.3195(4) 0.1084(11) Uiso 1.000000 GR
H18a H 0.2890(14) 0.3156(3) 1.1694(6) 0.1045(10) Uiso 1.000000 GR
H18b H 0.4060(4) 0.3827(3) 1.2328(12) 0.1045(10) Uiso 1.000000 GR
H18c H 0.2596(11) 0.3490(7) 1.2935(6) 0.1045(10) Uiso 1.000000 GR


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
C10 C11 1.424(2) . ?
C10 C17 1.433(2) . ?
C10 C13 1.414(2) . ?
C11 C7 1.429(2) . ?
C11 C16 1.415(2) . ?
C4 C12 1.488(2) . ?
C4 C5 1.387(2) . ?
C4 C3 1.389(2) . ?
C12 C7 1.489(3) . ?
C12 O1 1.222(2) . ?
C5 C6 1.375(3) . ?
C5 H5 0.9300 . ?
C7 C8 1.367(2) . ?
C3 C2 1.373(3) . ?
C3 H3 0.9300 . ?
C9 C8 1.397(3) . ?
C9 C17 1.367(2) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C2 C1 1.368(3) . ?
C2 H2 0.9300 . ?
C1 C6 1.370(3) . ?
C1 H1 0.9300 . ?
C6 H6 0.9300 . ?
C17 N1 1.407(2) . ?
C19 N1 1.457(3) . ?
C19 H19a 0.9600 . ?
C19 H19b 0.9600 . ?
C19 H19c 0.9600 . ?
C13 C14 1.357(3) . ?
C13 H13 0.9300 . ?
N1 C18 1.458(3) . ?
C14 C15 1.396(3) . ?
C14 H14 0.9300 . ?
C16 C15 1.356(3) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?
C18 H18a 0.9600 . ?
C18 H18b 0.9600 . ?
C18 H18c 0.9600 . ?

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
C17 C10 C11 119.76(15) . . ?
C13 C10 C11 118.05(16) . . ?
C13 C10 C17 122.14(17) . . ?
C7 C11 C10 118.93(16) . . ?
C16 C11 C10 118.33(16) . . ?
C16 C11 C7 122.58(16) . . ?
C5 C4 C12 122.01(16) . . ?
C3 C4 C12 119.42(16) . . ?
C3 C4 C5 118.48(17) . . ?
C7 C12 C4 118.70(16) . . ?
O1 C12 C4 120.25(17) . . ?
O1 C12 C7 121.04(17) . . ?
C6 C5 C4 120.32(18) . . ?
H5 C5 C4 119.84(11) . . ?
H5 C5 C6 119.84(12) . . ?
C12 C7 C11 122.33(16) . . ?
C8 C7 C11 118.68(16) . . ?
C8 C7 C12 118.95(16) . . ?
C2 C3 C4 120.55(19) . . ?
H3 C3 C4 119.73(11) . . ?
H3 C3 C2 119.73(12) . . ?
C17 C9 C8 120.80(18) . . ?
H9 C9 C8 119.60(11) . . ?
H9 C9 C17 119.60(11) . . ?
C9 C8 C7 122.36(18) . . ?
H8 C8 C7 118.82(11) . . ?
H8 C8 C9 118.82(11) . . ?
C1 C2 C3 120.36(19) . . ?
H2 C2 C3 119.82(12) . . ?
H2 C2 C1 119.82(12) . . ?
C6 C1 C2 119.8(2) . . ?
H1 C1 C2 120.08(12) . . ?
H1 C1 C6 120.08(13) . . ?
C1 C6 C5 120.5(2) . . ?
H6 C6 C5 119.77(12) . . ?
H6 C6 C1 119.77(13) . . ?
C9 C17 C10 118.82(16) . . ?
N1 C17 C10 118.64(16) . . ?
N1 C17 C9 122.50(17) . . ?
H19a C19 N1 109.5 . . ?
H19b C19 N1 109.5 . . ?
H19b C19 H19a 109.5 . . ?
H19c C19 N1 109.5 . . ?
H19c C19 H19a 109.5 . . ?
H19c C19 H19b 109.5 . . ?
C14 C13 C10 121.58(18) . . ?
H13 C13 C10 119.21(11) . . ?
H13 C13 C14 119.21(12) . . ?
C19 N1 C17 116.45(16) . . ?
C18 N1 C17 115.34(15) . . ?
C18 N1 C19 110.76(16) . . ?
C15 C14 C13 120.27(19) . . ?
H14 C14 C13 119.86(12) . . ?
H14 C14 C15 119.86(12) . . ?
C15 C16 C11 121.49(18) . . ?
H16 C16 C11 119.25(10) . . ?
H16 C16 C15 119.25(12) . . ?
C16 C15 C14 120.17(18) . . ?
H15 C15 C14 119.92(12) . . ?
H15 C15 C16 119.92(12) . . ?
H18a C18 N1 109.5 . . ?
H18b C18 N1 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 N1 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
