# 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. 
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data_cu_201110_qwy_5_199_2_0ma
_database_code_depnum_ccdc_archive 'CCDC 2049198'
loop_
_audit_author_name
_audit_author_address
'weiyi qi' 'Wuyi University'
_audit_update_record             
;
2020-12-09 deposited with the CCDC.	2021-02-19 downloaded from the CCDC.
;
_audit_creation_date             2020-11-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H27 N3 O6'
_chemical_formula_sum            'C20 H27 N3 O6'
_chemical_formula_weight         405.44
_chemical_absolute_configuration ad
_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 0.0181 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.2442(4)
_cell_length_b                   13.5824(6)
_cell_length_c                   17.5437(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1964.47(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9773
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      4.12
_shelx_estimated_absorpt_T_max   0.829
_shelx_estimated_absorpt_T_min   0.739
_exptl_absorpt_coefficient_mu    0.847
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1271 before and 0.0427 after correction.
The Ratio of minimum to maximum transmission is 0.8407.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            33070
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.265
_diffrn_reflns_theta_min         4.116
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3585
_reflns_number_total             3592
_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       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_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         0.164
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details 
;
 Flack x determined using 1517 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3592
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0265
_refine_ls_restrained_S_all      1.079
_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)+(0.0392P)²+0.3766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0684
_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 C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C13(H13), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C12(H12A,H12B), C18(H18A,H18B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C20(H20A,H20B,H20C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O6(H6)
;
_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 0.92473(18) 0.44781(10) 0.46043(9) 0.0367(3) Uani 1 1 d . . . . .
O2 O 0.81724(17) 0.29973(9) 0.43487(8) 0.0309(3) Uani 1 1 d . . . . .
O3 O 0.41354(15) 0.47589(9) 0.31152(7) 0.0243(3) Uani 1 1 d . . . . .
O4 O 0.44594(15) 0.75684(9) 0.18991(7) 0.0265(3) Uani 1 1 d . . . . .
H4 H 0.542707 0.738227 0.194047 0.040 Uiso 1 1 calc GR . . . .
O5 O 0.00593(16) 0.73536(10) 0.23645(8) 0.0320(3) Uani 1 1 d . . . . .
O6 O 0.27692(16) 1.15815(10) 0.29617(8) 0.0311(3) Uani 1 1 d . . . . .
H6 H 0.189997 1.182784 0.280037 0.047 Uiso 1 1 calc GR . . . .
N1 N 0.69708(19) 0.43100(11) 0.38528(8) 0.0239(3) Uani 1 1 d . . . . .
H1 H 0.640205 0.386801 0.360170 0.029 Uiso 1 1 calc R . . . .
N2 N 0.21450(18) 0.76311(10) 0.31700(8) 0.0217(3) Uani 1 1 d . . . . .
N3 N 0.02068(18) 0.88574(11) 0.39887(8) 0.0251(3) Uani 1 1 d . . . . .
C1 C 0.6892(2) 0.70438(13) 0.39983(10) 0.0245(4) Uani 1 1 d . . . . .
H1A H 0.753500 0.756621 0.419398 0.029 Uiso 1 1 calc R . . . .
C2 C 0.7482(2) 0.60873(13) 0.40295(10) 0.0244(4) Uani 1 1 d . . . . .
H2 H 0.853585 0.596219 0.422566 0.029 Uiso 1 1 calc R . . . .
C3 C 0.6522(2) 0.53119(13) 0.37718(9) 0.0222(3) Uani 1 1 d . . . . .
C4 C 0.5026(2) 0.55234(12) 0.34323(9) 0.0209(3) Uani 1 1 d . . . . .
C5 C 0.4465(2) 0.64919(13) 0.33755(9) 0.0212(3) Uani 1 1 d . . . . .
C6 C 0.5387(2) 0.72528(12) 0.36881(10) 0.0227(3) Uani 1 1 d . . . . .
C7 C 0.4664(2) 0.82728(12) 0.37088(10) 0.0241(4) Uani 1 1 d . . . . .
H7A H 0.488777 0.862038 0.322403 0.029 Uiso 1 1 calc R . . . .
H7B H 0.514790 0.865741 0.413096 0.029 Uiso 1 1 calc R . . . .
C8 C 0.2842(2) 0.81702(12) 0.38268(9) 0.0220(3) Uani 1 1 d . . . . .
H8 H 0.267031 0.775718 0.429167 0.026 Uiso 1 1 calc R . . . .
C9 C 0.2952(2) 0.67104(12) 0.29131(10) 0.0211(3) Uani 1 1 d . . . . .
H9 H 0.217433 0.615243 0.298211 0.025 Uiso 1 1 calc R . . . .
C10 C 0.0686(2) 0.78532(12) 0.28766(10) 0.0228(4) Uani 1 1 d . . . . .
C11 C -0.0162(2) 0.87733(12) 0.31738(10) 0.0240(4) Uani 1 1 d . . . . .
H11 H -0.135914 0.873586 0.308620 0.029 Uiso 1 1 calc R . . . .
C12 C 0.0564(2) 0.97062(13) 0.28009(10) 0.0247(4) Uani 1 1 d . . . . .
H12A H 0.080427 0.959608 0.225469 0.030 Uiso 1 1 calc R . . . .
H12B H -0.017803 1.027566 0.285160 0.030 Uiso 1 1 calc R . . . .
C13 C 0.2133(2) 0.98625(12) 0.32644(10) 0.0222(4) Uani 1 1 d . . . . .
H13 H 0.308268 0.965429 0.294887 0.027 Uiso 1 1 calc R . . . .
C14 C 0.1937(2) 0.91352(12) 0.39451(9) 0.0221(4) Uani 1 1 d . . . . .
H14 H 0.228959 0.945508 0.443100 0.027 Uiso 1 1 calc R . . . .
C15 C 0.8224(2) 0.39837(13) 0.42933(10) 0.0237(4) Uani 1 1 d . . . . .
C16 C 0.9529(3) 0.25714(15) 0.47447(12) 0.0371(5) Uani 1 1 d . . . . .
H16A H 1.053828 0.276314 0.449010 0.056 Uiso 1 1 calc GR . . . .
H16B H 0.942922 0.185238 0.474169 0.056 Uiso 1 1 calc GR . . . .
H16C H 0.954242 0.280829 0.527233 0.056 Uiso 1 1 calc GR . . . .
C17 C 0.2967(2) 0.43398(14) 0.36252(11) 0.0316(4) Uani 1 1 d . . . . .
H17A H 0.234636 0.382981 0.335831 0.047 Uiso 1 1 calc GR . . . .
H17B H 0.222715 0.485582 0.380328 0.047 Uiso 1 1 calc GR . . . .
H17C H 0.352659 0.404720 0.406271 0.047 Uiso 1 1 calc GR . . . .
C18 C 0.3409(2) 0.67709(12) 0.20604(10) 0.0226(3) Uani 1 1 d . . . . .
H18A H 0.394294 0.614886 0.190662 0.027 Uiso 1 1 calc R . . . .
H18B H 0.240760 0.684220 0.175416 0.027 Uiso 1 1 calc R . . . .
C19 C 0.2422(2) 1.09046(12) 0.35564(11) 0.0269(4) Uani 1 1 d . . . . .
H19A H 0.144596 1.113029 0.383512 0.032 Uiso 1 1 calc R . . . .
H19B H 0.333957 1.089691 0.392025 0.032 Uiso 1 1 calc R . . . .
C20 C -0.0820(2) 0.95735(15) 0.43815(12) 0.0325(4) Uani 1 1 d . . . . .
H20A H -0.046359 0.963806 0.491201 0.049 Uiso 1 1 calc GR . . . .
H20B H -0.194985 0.934905 0.436957 0.049 Uiso 1 1 calc GR . . . .
H20C H -0.073612 1.021319 0.412623 0.049 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 C15 1.208(2) . ?
O2 C15 1.344(2) . ?
O2 C16 1.438(2) . ?
O3 C4 1.388(2) . ?
O3 C17 1.433(2) . ?
O4 H4 0.8400 . ?
O4 C18 1.415(2) . ?
O5 C10 1.239(2) . ?
O6 H6 0.8400 . ?
O6 C19 1.420(2) . ?
N1 H1 0.8800 . ?
N1 C3 1.417(2) . ?
N1 C15 1.364(2) . ?
N2 C8 1.481(2) . ?
N2 C9 1.486(2) . ?
N2 C10 1.343(2) . ?
N3 C11 1.466(2) . ?
N3 C14 1.477(2) . ?
N3 C20 1.462(2) . ?
C1 H1A 0.9500 . ?
C1 C2 1.388(2) . ?
C1 C6 1.385(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(3) . ?
C3 C4 1.399(2) . ?
C4 C5 1.398(2) . ?
C5 C6 1.395(2) . ?
C5 C9 1.518(2) . ?
C6 C7 1.508(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.523(3) . ?
C8 H8 1.0000 . ?
C8 C14 1.523(2) . ?
C9 H9 1.0000 . ?
C9 C18 1.545(2) . ?
C10 C11 1.524(2) . ?
C11 H11 1.0000 . ?
C11 C12 1.546(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.542(2) . ?
C13 H13 1.0000 . ?
C13 C14 1.558(2) . ?
C13 C19 1.524(2) . ?
C14 H14 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C15 O2 C16 114.29(16) . . ?
C4 O3 C17 113.74(13) . . ?
C18 O4 H4 109.5 . . ?
C19 O6 H6 109.5 . . ?
C3 N1 H1 117.7 . . ?
C15 N1 H1 117.7 . . ?
C15 N1 C3 124.51(15) . . ?
C8 N2 C9 118.56(13) . . ?
C10 N2 C8 122.33(14) . . ?
C10 N2 C9 118.27(14) . . ?
C11 N3 C14 99.77(13) . . ?
C20 N3 C11 113.03(15) . . ?
C20 N3 C14 114.43(14) . . ?
C2 C1 H1A 119.3 . . ?
C6 C1 H1A 119.3 . . ?
C6 C1 C2 121.42(16) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.71(16) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 N1 123.01(16) . . ?
C2 C3 C4 118.93(16) . . ?
C4 C3 N1 118.05(15) . . ?
O3 C4 C3 118.89(15) . . ?
O3 C4 C5 120.03(15) . . ?
C5 C4 C3 121.00(15) . . ?
C4 C5 C9 119.61(15) . . ?
C6 C5 C4 119.29(15) . . ?
C6 C5 C9 120.85(15) . . ?
C1 C6 C5 119.38(16) . . ?
C1 C6 C7 122.18(15) . . ?
C5 C6 C7 118.37(15) . . ?
C6 C7 H7A 110.1 . . ?
C6 C7 H7B 110.1 . . ?
C6 C7 C8 107.97(14) . . ?
H7A C7 H7B 108.4 . . ?
C8 C7 H7A 110.1 . . ?
C8 C7 H7B 110.1 . . ?
N2 C8 C7 108.81(14) . . ?
N2 C8 H8 107.6 . . ?
N2 C8 C14 109.96(14) . . ?
C7 C8 H8 107.6 . . ?
C14 C8 C7 115.05(14) . . ?
C14 C8 H8 107.6 . . ?
N2 C9 C5 111.74(13) . . ?
N2 C9 H9 108.3 . . ?
N2 C9 C18 110.99(13) . . ?
C5 C9 H9 108.3 . . ?
C5 C9 C18 109.10(14) . . ?
C18 C9 H9 108.3 . . ?
O5 C10 N2 121.91(16) . . ?
O5 C10 C11 120.40(16) . . ?
N2 C10 C11 117.65(15) . . ?
N3 C11 C10 107.59(14) . . ?
N3 C11 H11 111.0 . . ?
N3 C11 C12 105.56(13) . . ?
C10 C11 H11 111.0 . . ?
C10 C11 C12 110.47(14) . . ?
C12 C11 H11 111.0 . . ?
C11 C12 H12A 111.3 . . ?
C11 C12 H12B 111.3 . . ?
H12A C12 H12B 109.2 . . ?
C13 C12 C11 102.37(13) . . ?
C13 C12 H12A 111.3 . . ?
C13 C12 H12B 111.3 . . ?
C12 C13 H13 109.0 . . ?
C12 C13 C14 103.30(14) . . ?
C14 C13 H13 109.0 . . ?
C19 C13 C12 115.86(14) . . ?
C19 C13 H13 109.0 . . ?
C19 C13 C14 110.33(14) . . ?
N3 C14 C8 105.10(13) . . ?
N3 C14 C13 107.55(14) . . ?
N3 C14 H14 110.3 . . ?
C8 C14 C13 112.98(14) . . ?
C8 C14 H14 110.3 . . ?
C13 C14 H14 110.3 . . ?
O1 C15 O2 122.91(16) . . ?
O1 C15 N1 127.16(16) . . ?
O2 C15 N1 109.93(15) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 C9 112.56(13) . . ?
O4 C18 H18A 109.1 . . ?
O4 C18 H18B 109.1 . . ?
C9 C18 H18A 109.1 . . ?
C9 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
O6 C19 C13 112.70(15) . . ?
O6 C19 H19A 109.1 . . ?
O6 C19 H19B 109.1 . . ?
C13 C19 H19A 109.1 . . ?
C13 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
