# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1970137'
loop_
_audit_author_name
_audit_author_address
youliangShao
;Lanzhou University
China
;
_audit_update_record             
;
2019-12-05 deposited with the CCDC.	2020-07-23 downloaded from the CCDC.
;
_audit_creation_date             2019-11-25
_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         'C16 H17 N O6'
_chemical_formula_sum            'C16 H17 N O6'
_chemical_formula_weight         319.30
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.975(8)
_cell_length_b                   4.999(2)
_cell_length_c                   17.260(7)
_cell_angle_alpha                90
_cell_angle_beta                 110.614(7)
_cell_angle_gamma                90
_cell_volume                     1613.3(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1251
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.42
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1176 before and 0.0458 after correction.
The Ratio of minimum to maximum transmission is 0.6999.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_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    1.315
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7458
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.021
_diffrn_reflns_theta_max         25.021
_diffrn_reflns_theta_min         1.089
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1493
_reflns_number_total             2819
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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         0.285
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2819
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1179
_refine_ls_R_factor_gt           0.0609
_refine_ls_restrained_S_all      0.996
_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)+(0.1250P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1694
_refine_ls_wR_factor_ref         0.2168
_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:
 C13(H13A,H13B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C16(H16A,H16B,H16C)
;
_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 0.38614(14) 0.0598(5) 0.70511(13) 0.0869(8) Uani 1 1 d . . . . .
O2 O 0.39085(13) -0.1850(5) 0.59853(14) 0.0805(8) Uani 1 1 d . . . . .
O3 O 0.39457(15) 0.0343(6) 0.45174(15) 0.0982(9) Uani 1 1 d . . . . .
O4 O 0.28742(17) -0.0778(7) 0.36360(16) 0.1118(11) Uani 1 1 d . . . . .
O5 O 0.10790(15) 0.0908(6) 0.35132(15) 0.1004(10) Uani 1 1 d . . . . .
O6 O 0.10661(12) 0.2924(5) 0.23557(12) 0.0755(8) Uani 1 1 d . . . . .
N1 N 0.27113(14) 0.3646(6) 0.58655(14) 0.0599(7) Uani 1 1 d . . . . .
C1 C 0.2680(2) 0.4429(8) 0.66240(19) 0.0740(11) Uani 1 1 d . . . . .
H1 H 0.297417 0.361556 0.710882 0.089 Uiso 1 1 calc R . . . .
C2 C 0.2223(2) 0.6361(9) 0.6657(2) 0.0861(12) Uani 1 1 d . . . . .
H2 H 0.220530 0.686975 0.716747 0.103 Uiso 1 1 calc R . . . .
C3 C 0.1769(2) 0.7636(9) 0.5933(3) 0.0864(12) Uani 1 1 d . . . . .
H3 H 0.146814 0.901326 0.596834 0.104 Uiso 1 1 calc R . . . .
C4 C 0.17762(19) 0.6835(8) 0.5185(2) 0.0756(10) Uani 1 1 d . . . . .
H4 H 0.147159 0.764158 0.470482 0.091 Uiso 1 1 calc R . . . .
C5 C 0.22446(17) 0.4778(7) 0.51324(18) 0.0597(9) Uani 1 1 d . . . . .
C6 C 0.23758(17) 0.3599(7) 0.44718(18) 0.0601(9) Uani 1 1 d . . . . .
C7 C 0.29376(17) 0.1793(7) 0.48068(17) 0.0582(8) Uani 1 1 d . . . . .
C8 C 0.31444(17) 0.1791(7) 0.56727(17) 0.0578(9) Uani 1 1 d . . . . .
C9 C 0.36634(18) 0.0177(8) 0.6312(2) 0.0667(10) Uani 1 1 d . . . . .
C10 C 0.4478(2) -0.3403(9) 0.6561(3) 0.0997(14) Uani 1 1 d . . . . .
H10A H 0.461036 -0.482399 0.626997 0.149 Uiso 1 1 calc GR . . . .
H10B H 0.431663 -0.414452 0.697793 0.149 Uiso 1 1 calc GR . . . .
H10C H 0.488371 -0.227088 0.681770 0.149 Uiso 1 1 calc GR . . . .
C11 C 0.3243(2) 0.0270(8) 0.4274(2) 0.0728(10) Uani 1 1 d . . . . .
C12 C 0.4250(3) -0.1424(14) 0.4038(3) 0.145(2) Uani 1 1 d . . . . .
H12A H 0.422905 -0.053908 0.353677 0.218 Uiso 1 1 calc GR . . . .
H12B H 0.397926 -0.305386 0.390527 0.218 Uiso 1 1 calc GR . . . .
H12C H 0.473861 -0.182515 0.436208 0.218 Uiso 1 1 calc GR . . . .
C13 C 0.19733(19) 0.4235(7) 0.35725(17) 0.0688(10) Uani 1 1 d . . . . .
H13A H 0.181274 0.607833 0.352941 0.083 Uiso 1 1 calc R . . . .
H13B H 0.229885 0.407575 0.327001 0.083 Uiso 1 1 calc R . . . .
C14 C 0.13366(18) 0.2464(7) 0.31697(19) 0.0639(9) Uani 1 1 d . . . . .
C15 C 0.0445(2) 0.1331(10) 0.1875(2) 0.0940(13) Uani 1 1 d . . . . .
H15A H 0.005056 0.165669 0.206643 0.113 Uiso 1 1 calc R . . . .
H15B H 0.056196 -0.055849 0.193907 0.113 Uiso 1 1 calc R . . . .
C16 C 0.0243(2) 0.2110(12) 0.0999(2) 0.1184(18) Uani 1 1 d . . . . .
H16A H -0.017260 0.111952 0.067330 0.178 Uiso 1 1 calc GR . . . .
H16B H 0.063092 0.172934 0.081044 0.178 Uiso 1 1 calc GR . . . .
H16C H 0.013814 0.398946 0.094352 0.178 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 C9 1.214(4) . ?
O2 C9 1.334(4) . ?
O2 C10 1.444(4) . ?
O3 C11 1.317(4) . ?
O3 C12 1.479(5) . ?
O4 C11 1.207(4) . ?
O5 C14 1.198(4) . ?
O6 C14 1.336(4) . ?
O6 C15 1.462(4) . ?
N1 C1 1.389(4) . ?
N1 C5 1.400(4) . ?
N1 C8 1.386(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.344(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.411(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.356(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.415(5) . ?
C5 C6 1.388(4) . ?
C6 C7 1.397(5) . ?
C6 C13 1.509(4) . ?
C7 C8 1.403(4) . ?
C7 C11 1.481(5) . ?
C8 C9 1.462(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.504(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.472(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C9 O2 C10 115.8(3) . . ?
C11 O3 C12 114.0(3) . . ?
C14 O6 C15 116.9(3) . . ?
C1 N1 C5 120.1(3) . . ?
C8 N1 C1 130.8(3) . . ?
C8 N1 C5 109.1(2) . . ?
N1 C1 H1 120.0 . . ?
C2 C1 N1 119.9(3) . . ?
C2 C1 H1 120.0 . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.4(4) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.4(4) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.3(3) . . ?
C5 C4 H4 119.8 . . ?
N1 C5 C4 118.7(3) . . ?
C6 C5 N1 108.2(3) . . ?
C6 C5 C4 133.0(3) . . ?
C5 C6 C7 106.9(3) . . ?
C5 C6 C13 124.7(3) . . ?
C7 C6 C13 128.4(3) . . ?
C6 C7 C8 109.5(3) . . ?
C6 C7 C11 121.4(3) . . ?
C8 C7 C11 129.1(3) . . ?
N1 C8 C7 106.3(3) . . ?
N1 C8 C9 121.7(3) . . ?
C7 C8 C9 131.9(3) . . ?
O1 C9 O2 122.9(3) . . ?
O1 C9 C8 125.4(4) . . ?
O2 C9 C8 111.7(3) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 C7 114.4(3) . . ?
O4 C11 O3 122.8(4) . . ?
O4 C11 C7 122.5(4) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C13 H13A 108.7 . . ?
C6 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 C6 114.1(3) . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
O5 C14 O6 123.2(3) . . ?
O5 C14 C13 126.4(3) . . ?
O6 C14 C13 110.4(3) . . ?
O6 C15 H15A 110.1 . . ?
O6 C15 H15B 110.1 . . ?
O6 C15 C16 108.1(4) . . ?
H15A C15 H15B 108.4 . . ?
C16 C15 H15A 110.1 . . ?
C16 C15 H15B 110.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
N1 C1 C2 C3 -0.1(6) . . . . ?
N1 C5 C6 C7 -1.5(4) . . . . ?
N1 C5 C6 C13 178.8(3) . . . . ?
N1 C8 C9 O1 -14.2(5) . . . . ?
N1 C8 C9 O2 166.4(3) . . . . ?
C1 N1 C5 C4 3.9(4) . . . . ?
C1 N1 C5 C6 -178.4(3) . . . . ?
C1 N1 C8 C7 179.2(3) . . . . ?
C1 N1 C8 C9 2.4(5) . . . . ?
C1 C2 C3 C4 2.2(6) . . . . ?
C2 C3 C4 C5 -1.3(6) . . . . ?
C3 C4 C5 N1 -1.7(5) . . . . ?
C3 C4 C5 C6 -178.8(4) . . . . ?
C4 C5 C6 C7 175.8(3) . . . . ?
C4 C5 C6 C13 -3.9(6) . . . . ?
C5 N1 C1 C2 -3.0(5) . . . . ?
C5 N1 C8 C7 0.0(3) . . . . ?
C5 N1 C8 C9 -176.8(3) . . . . ?
C5 C6 C7 C8 1.5(4) . . . . ?
C5 C6 C7 C11 -176.9(3) . . . . ?
C5 C6 C13 C14 -91.8(4) . . . . ?
C6 C7 C8 N1 -0.9(4) . . . . ?
C6 C7 C8 C9 175.4(3) . . . . ?
C6 C7 C11 O3 131.0(3) . . . . ?
C6 C7 C11 O4 -43.7(5) . . . . ?
C6 C13 C14 O5 10.3(6) . . . . ?
C6 C13 C14 O6 -172.1(3) . . . . ?
C7 C6 C13 C14 88.6(4) . . . . ?
C7 C8 C9 O1 169.9(3) . . . . ?
C7 C8 C9 O2 -9.4(5) . . . . ?
C8 N1 C1 C2 177.8(3) . . . . ?
C8 N1 C5 C4 -176.8(3) . . . . ?
C8 N1 C5 C6 1.0(3) . . . . ?
C8 C7 C11 O3 -47.1(5) . . . . ?
C8 C7 C11 O4 138.2(4) . . . . ?
C10 O2 C9 O1 -5.4(5) . . . . ?
C10 O2 C9 C8 174.0(3) . . . . ?
C11 C7 C8 N1 177.3(3) . . . . ?
C11 C7 C8 C9 -6.4(6) . . . . ?
C12 O3 C11 O4 -11.8(6) . . . . ?
C12 O3 C11 C7 173.5(4) . . . . ?
C13 C6 C7 C8 -178.8(3) . . . . ?
C13 C6 C7 C11 2.8(5) . . . . ?
C14 O6 C15 C16 -178.9(4) . . . . ?
C15 O6 C14 O5 -2.8(5) . . . . ?
C15 O6 C14 C13 179.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
