# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_cxy0622_0m
_database_code_depnum_ccdc_archive 'CCDC 2060387'
loop_
_audit_author_name
_audit_author_address
'Jun WANG'
;Hong Kong Baptist University
China
;
_audit_update_record             
;
2021-02-02 deposited with the CCDC.	2021-03-02 downloaded from the CCDC.
;
_audit_creation_date             2019-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H17 N O6'
_chemical_formula_sum            'C17 H17 N O6'
_chemical_formula_weight         331.31
_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                   7.180(3)
_cell_length_b                   8.862(4)
_cell_length_c                   12.266(6)
_cell_angle_alpha                84.056(17)
_cell_angle_beta                 84.296(15)
_cell_angle_gamma                84.884(14)
_cell_volume                     770.0(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7488
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.505
_cell_measurement_theta_min      2.316
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1041 before and 0.0502 after correction. The Ratio of minimum to maximum transmission is 0.9662. 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    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14957
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.545
_diffrn_reflns_theta_min         2.318
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2904
_reflns_number_total             3549
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3549
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.034
_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)+(0.0484P)²+0.2547P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.0994
_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 Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12)
2.d X=CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C15(H15A,H15B,H15C)
;
_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 0.75218(13) 0.37714(10) 0.49532(7) 0.0170(2) Uani 1 1 d . . . . .
O2 O 1.11919(14) -0.05493(10) 0.68677(8) 0.0202(2) Uani 1 1 d . . . . .
O3 O 1.07083(13) 0.19708(10) 0.69766(8) 0.0199(2) Uani 1 1 d . . . . .
O4 O 0.64524(14) 0.15337(10) 0.64650(7) 0.0182(2) Uani 1 1 d . . . . .
O5 O 0.60047(13) 0.46072(10) 0.87498(7) 0.0147(2) Uani 1 1 d . . . . .
O6 O 0.32851(12) 0.34754(10) 0.85191(7) 0.0154(2) Uani 1 1 d . . . . .
C17 C 0.92777(19) -0.10927(15) 0.88838(11) 0.0181(3) Uani 1 1 d . . . . .
H17A H 1.006958 -0.188878 0.857811 0.022 Uiso 1 1 calc R . . . .
H17B H 0.850234 -0.130064 0.954682 0.022 Uiso 1 1 calc R . . . .
N1 N 0.42878(16) -0.04286(13) 0.87208(9) 0.0182(2) Uani 1 1 d . . . . .
C1 C 0.79749(19) 0.43965(16) 0.38414(10) 0.0189(3) Uani 1 1 d . . . . .
H1A H 0.692910 0.509963 0.360258 0.028 Uiso 1 1 calc GR . . . .
H1B H 0.819594 0.357138 0.335893 0.028 Uiso 1 1 calc GR . . . .
H1C H 0.910925 0.494532 0.380356 0.028 Uiso 1 1 calc GR . . . .
C2 C 0.72010(17) 0.47477(14) 0.57345(10) 0.0137(3) Uani 1 1 d . . . . .
C3 C 0.67255(17) 0.41052(14) 0.68264(10) 0.0124(3) Uani 1 1 d . . . . .
C4 C 0.64492(17) 0.24838(14) 0.71065(10) 0.0123(2) Uani 1 1 d . . . . .
C5 C 0.61616(17) 0.19927(13) 0.83556(10) 0.0118(2) Uani 1 1 d . . . . .
C6 C 0.80871(17) 0.16273(14) 0.88486(10) 0.0139(3) Uani 1 1 d . . . . .
H6A H 0.880755 0.254032 0.870769 0.017 Uiso 1 1 calc R . . . .
H6B H 0.785860 0.140288 0.965601 0.017 Uiso 1 1 calc R . . . .
C7 C 0.92548(17) 0.03049(14) 0.83864(10) 0.0140(3) Uani 1 1 d . . . . .
C8 C 1.04500(18) 0.06804(14) 0.73442(10) 0.0146(3) Uani 1 1 d . . . . .
C9 C 1.2381(2) -0.02353(17) 0.58620(12) 0.0264(3) Uani 1 1 d . . . . .
H9A H 1.165143 0.038466 0.532027 0.040 Uiso 1 1 calc GR . . . .
H9B H 1.286533 -0.119578 0.556894 0.040 Uiso 1 1 calc GR . . . .
H9C H 1.343395 0.031825 0.601528 0.040 Uiso 1 1 calc GR . . . .
C10 C 0.73346(19) 0.63087(15) 0.55153(11) 0.0191(3) Uani 1 1 d . . . . .
H10 H 0.763537 0.673788 0.478350 0.023 Uiso 1 1 calc R . . . .
C11 C 0.7026(2) 0.72335(16) 0.63703(12) 0.0227(3) Uani 1 1 d . . . . .
H11 H 0.711873 0.829817 0.621484 0.027 Uiso 1 1 calc R . . . .
C12 C 0.6589(2) 0.66451(15) 0.74422(11) 0.0196(3) Uani 1 1 d . . . . .
H12 H 0.639314 0.729107 0.802152 0.023 Uiso 1 1 calc R . . . .
C13 C 0.64417(17) 0.51042(14) 0.76539(10) 0.0139(3) Uani 1 1 d . . . . .
C14 C 0.50263(17) 0.32731(14) 0.89427(10) 0.0130(3) Uani 1 1 d . . . . .
H14 H 0.485649 0.296246 0.975137 0.016 Uiso 1 1 calc R . . . .
C15 C 0.20273(19) 0.46167(16) 0.90011(12) 0.0211(3) Uani 1 1 d . . . . .
H15A H 0.183125 0.435331 0.979779 0.032 Uiso 1 1 calc GR . . . .
H15B H 0.082214 0.467613 0.868136 0.032 Uiso 1 1 calc GR . . . .
H15C H 0.256626 0.560328 0.885478 0.032 Uiso 1 1 calc GR . . . .
C16 C 0.50931(17) 0.06326(14) 0.85352(10) 0.0132(3) Uani 1 1 d . . . . .


_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 1.4352(16) . ?
O1 C2 1.3462(16) . ?
O2 C8 1.3340(16) . ?
O2 C9 1.4458(17) . ?
O3 C8 1.2083(16) . ?
O4 C4 1.2102(15) . ?
O5 C13 1.3847(16) . ?
O5 C14 1.4158(15) . ?
O6 C14 1.3909(16) . ?
O6 C15 1.4293(16) . ?
C17 H17A 0.9500 . ?
C17 H17B 0.9500 . ?
C17 C7 1.3223(19) . ?
N1 C16 1.1389(17) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.4213(18) . ?
C2 C10 1.3917(19) . ?
C3 C4 1.4687(18) . ?
C3 C13 1.4031(18) . ?
C4 C5 1.5475(18) . ?
C5 C6 1.5580(18) . ?
C5 C14 1.5356(17) . ?
C5 C16 1.4718(18) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5051(18) . ?
C7 C8 1.4920(18) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 0.9500 . ?
C10 C11 1.386(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.380(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.3749(19) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C2 O1 C1 117.56(10) . . ?
C8 O2 C9 114.84(11) . . ?
C13 O5 C14 115.48(9) . . ?
C14 O6 C15 113.90(10) . . ?
H17A C17 H17B 120.0 . . ?
C7 C17 H17A 120.0 . . ?
C7 C17 H17B 120.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 116.55(11) . . ?
O1 C2 C10 123.16(12) . . ?
C10 C2 C3 120.30(12) . . ?
C2 C3 C4 123.17(11) . . ?
C13 C3 C2 117.14(12) . . ?
C13 C3 C4 119.64(11) . . ?
O4 C4 C3 126.47(12) . . ?
O4 C4 C5 118.92(11) . . ?
C3 C4 C5 114.60(10) . . ?
C4 C5 C6 110.74(10) . . ?
C14 C5 C4 109.60(10) . . ?
C14 C5 C6 109.50(10) . . ?
C16 C5 C4 109.23(10) . . ?
C16 C5 C6 109.41(10) . . ?
C16 C5 C14 108.33(10) . . ?
C5 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 C5 113.77(10) . . ?
C7 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C17 C7 C6 122.65(12) . . ?
C17 C7 C8 121.72(12) . . ?
C8 C7 C6 115.59(11) . . ?
O2 C8 C7 113.09(11) . . ?
O3 C8 O2 123.97(12) . . ?
O3 C8 C7 122.94(11) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 H10 120.2 . . ?
C11 C10 C2 119.64(13) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.59(13) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 120.7 . . ?
C13 C12 C11 118.59(12) . . ?
C13 C12 H12 120.7 . . ?
O5 C13 C3 122.35(11) . . ?
C12 C13 O5 114.91(11) . . ?
C12 C13 C3 122.74(12) . . ?
O5 C14 C5 109.16(10) . . ?
O5 C14 H14 109.6 . . ?
O6 C14 O5 112.03(10) . . ?
O6 C14 C5 106.70(10) . . ?
O6 C14 H14 109.6 . . ?
C5 C14 H14 109.6 . . ?
O6 C15 H15A 109.5 . . ?
O6 C15 H15B 109.5 . . ?
O6 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C5 176.97(13) . . ?

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
O1 C2 C3 C4 -4.43(18) . . . . ?
O1 C2 C3 C13 178.18(11) . . . . ?
O1 C2 C10 C11 -178.45(12) . . . . ?
O4 C4 C5 C6 94.28(13) . . . . ?
O4 C4 C5 C14 -144.81(12) . . . . ?
O4 C4 C5 C16 -26.28(15) . . . . ?
C17 C7 C8 O2 13.37(18) . . . . ?
C17 C7 C8 O3 -166.69(13) . . . . ?
C1 O1 C2 C3 179.03(11) . . . . ?
C1 O1 C2 C10 -1.62(18) . . . . ?
C2 C3 C4 O4 -5.6(2) . . . . ?
C2 C3 C4 C5 173.41(11) . . . . ?
C2 C3 C13 O5 -178.87(11) . . . . ?
C2 C3 C13 C12 0.63(19) . . . . ?
C2 C10 C11 C12 0.1(2) . . . . ?
C3 C2 C10 C11 0.9(2) . . . . ?
C3 C4 C5 C6 -84.81(12) . . . . ?
C3 C4 C5 C14 36.10(14) . . . . ?
C3 C4 C5 C16 154.64(10) . . . . ?
C4 C3 C13 O5 3.63(18) . . . . ?
C4 C3 C13 C12 -176.86(12) . . . . ?
C4 C5 C6 C7 -63.29(14) . . . . ?
C4 C5 C14 O5 -59.06(13) . . . . ?
C4 C5 C14 O6 62.20(12) . . . . ?
C5 C6 C7 C17 -96.45(15) . . . . ?
C5 C6 C7 C8 85.72(14) . . . . ?
C6 C5 C14 O5 62.59(13) . . . . ?
C6 C5 C14 O6 -176.15(10) . . . . ?
C6 C7 C8 O2 -168.77(11) . . . . ?
C6 C7 C8 O3 11.16(18) . . . . ?
C9 O2 C8 O3 0.86(19) . . . . ?
C9 O2 C8 C7 -179.20(12) . . . . ?
C10 C2 C3 C4 176.20(12) . . . . ?
C10 C2 C3 C13 -1.20(18) . . . . ?
C10 C11 C12 C13 -0.6(2) . . . . ?
C11 C12 C13 O5 179.80(12) . . . . ?
C11 C12 C13 C3 0.3(2) . . . . ?
C13 O5 C14 O6 -62.11(13) . . . . ?
C13 O5 C14 C5 55.84(13) . . . . ?
C13 C3 C4 O4 171.74(12) . . . . ?
C13 C3 C4 C5 -9.26(16) . . . . ?
C14 O5 C13 C3 -28.37(16) . . . . ?
C14 O5 C13 C12 152.09(11) . . . . ?
C14 C5 C6 C7 175.74(10) . . . . ?
C15 O6 C14 O5 -61.91(13) . . . . ?
C15 O6 C14 C5 178.68(10) . . . . ?
C16 C5 C6 C7 57.16(14) . . . . ?
C16 C5 C14 O5 -178.15(9) . . . . ?
C16 C5 C14 O6 -56.89(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
