# 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_220191102hjq_0m
_database_code_depnum_ccdc_archive 'CCDC 2036191'
loop_
_audit_author_name
_audit_author_address
Oxazolinose
;shanghai institute of materia medica, Chinese academy of sciences
China
;
_audit_update_record             
;
2020-10-09 deposited with the CCDC.	2021-01-20 downloaded from the CCDC.
;
_audit_creation_date             2019-11-04
_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         'C14 H15 N O7'
_chemical_formula_sum            'C14 H15 N O7'
_chemical_formula_weight         309.27
_chemical_absolute_configuration rmad
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.7659(3)
_cell_length_b                   12.6787(7)
_cell_length_c                   11.0168(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.803(2)
_cell_angle_gamma                90
_cell_volume                     662.28(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5743
_cell_measurement_temperature    100
_cell_measurement_theta_max      74.704
_cell_measurement_theta_min      4.034
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.909
_exptl_absorpt_coefficient_mu    1.078
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6240
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1610 before and 0.0569 after correction. The Ratio of minimum to maximum transmission is 0.8278. 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    1.551
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6504
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        66.583
_diffrn_reflns_theta_max         66.583
_diffrn_reflns_theta_min         4.033
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_full    0.916
_reflns_Friedel_fraction_max     0.916
_reflns_number_gt                2196
_reflns_number_total             2250
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 951 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2250
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0279
_refine_ls_restrained_S_all      1.042
_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)+(0.0331P)²+0.0830P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0663
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C9(H9), C10(H10), C14(H14), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C4(H4A)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O1(H1), O3(H3)
;
_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
O5 O 0.0540(3) 0.43705(12) 0.74435(14) 0.0198(3) Uani 1 1 d . . . . .
O2 O 0.0046(3) 0.55988(12) 0.48089(13) 0.0166(3) Uani 1 1 d . . . . .
O4 O -0.1825(3) 0.26298(12) 0.57828(14) 0.0210(3) Uani 1 1 d . . . . .
H4 H -0.049363 0.219341 0.581166 0.032 Uiso 1 1 calc GR . . . .
O7 O 1.0598(3) 0.59527(13) 1.12061(14) 0.0228(4) Uani 1 1 d . . . . .
O1 O -0.3620(3) 0.67387(13) 0.32006(15) 0.0236(4) Uani 1 1 d . . . . .
H1 H -0.484824 0.713337 0.345617 0.035 Uiso 1 1 calc GR . . . .
O6 O 0.9241(4) 0.73630(14) 0.99491(15) 0.0257(4) Uani 1 1 d . . . . .
O3 O -0.1103(4) 0.32837(14) 0.32553(14) 0.0285(4) Uani 1 1 d . . . . .
H3 H -0.133140 0.264278 0.341155 0.043 Uiso 1 1 calc GR . . . .
N1 N 0.0902(4) 0.60614(16) 0.68257(16) 0.0186(4) Uani 1 1 d . . . . .
C12 C -0.4290(4) 0.56669(19) 0.34278(18) 0.0181(4) Uani 1 1 d . . . . .
H12A H -0.523775 0.534509 0.267645 0.022 Uiso 1 1 calc R . . . .
H12B H -0.559571 0.563111 0.407067 0.022 Uiso 1 1 calc R . . . .
C2 C 0.7542(5) 0.65125(18) 0.96425(19) 0.0195(4) Uani 1 1 d . . . . .
C3 C 0.8360(4) 0.5662(2) 1.04002(18) 0.0191(4) Uani 1 1 d . . . . .
C11 C -0.1616(4) 0.50646(17) 0.38324(18) 0.0161(4) Uani 1 1 d . . . . .
H11 H -0.046629 0.504948 0.312179 0.019 Uiso 1 1 calc R . . . .
C9 C -0.1531(5) 0.44478(17) 0.63785(19) 0.0173(4) Uani 1 1 d . . . . .
H9 H -0.347924 0.433698 0.661682 0.021 Uiso 1 1 calc R . . . .
C7 C 0.5389(5) 0.64387(19) 0.87221(19) 0.0196(4) Uani 1 1 d . . . . .
H7 H 0.485699 0.701838 0.820270 0.024 Uiso 1 1 calc R . . . .
C8 C 0.1747(5) 0.53384(17) 0.75888(19) 0.0165(4) Uani 1 1 d . . . . .
C5 C 0.4809(5) 0.46147(18) 0.93585(19) 0.0201(4) Uani 1 1 d . . . . .
H5 H 0.381964 0.396541 0.925320 0.024 Uiso 1 1 calc R . . . .
C4 C 0.7035(5) 0.47008(19) 1.02837(19) 0.0220(5) Uani 1 1 d . . . . .
H4A H 0.759870 0.412471 1.080354 0.026 Uiso 1 1 calc R . . . .
C6 C 0.4007(5) 0.54560(18) 0.85880(19) 0.0182(4) Uani 1 1 d . . . . .
C10 C -0.1175(4) 0.55873(18) 0.59349(18) 0.0165(4) Uani 1 1 d . . . . .
H10 H -0.300070 0.598166 0.587486 0.020 Uiso 1 1 calc R . . . .
C14 C -0.0852(4) 0.36303(17) 0.54332(18) 0.0164(4) Uani 1 1 d . . . . .
H14 H 0.123965 0.359756 0.541481 0.020 Uiso 1 1 calc R . . . .
C13 C -0.2218(4) 0.39084(18) 0.41531(19) 0.0184(4) Uani 1 1 d . . . . .
H13 H -0.430223 0.379593 0.411514 0.022 Uiso 1 1 calc R . . . .
C1 C 1.0899(5) 0.70700(19) 1.1058(2) 0.0225(5) Uani 1 1 d . . . . .
H1A H 1.290444 0.725310 1.101076 0.027 Uiso 1 1 calc R . . . .
H1B H 1.022796 0.744845 1.175986 0.027 Uiso 1 1 calc R . . . .


_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
O5 C9 1.458(3) . ?
O5 C8 1.358(3) . ?
O2 C11 1.439(3) . ?
O2 C10 1.422(2) . ?
O4 H4 0.8400 . ?
O4 C14 1.417(3) . ?
O7 C3 1.368(3) . ?
O7 C1 1.435(3) . ?
O1 H1 0.8400 . ?
O1 C12 1.424(3) . ?
O6 C2 1.370(3) . ?
O6 C1 1.435(3) . ?
O3 H3 0.8400 . ?
O3 C13 1.412(3) . ?
N1 C8 1.281(3) . ?
N1 C10 1.452(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.514(3) . ?
C2 C3 1.395(3) . ?
C2 C7 1.371(3) . ?
C3 C4 1.372(4) . ?
C11 H11 1.0000 . ?
C11 C13 1.542(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.540(3) . ?
C9 C14 1.527(3) . ?
C7 H7 0.9500 . ?
C7 C6 1.410(3) . ?
C8 C6 1.468(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.399(3) . ?
C5 C6 1.392(3) . ?
C4 H4A 0.9500 . ?
C10 H10 1.0000 . ?
C14 H14 1.0000 . ?
C14 C13 1.533(3) . ?
C13 H13 1.0000 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?

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
C8 O5 C9 106.17(17) . . ?
C10 O2 C11 113.86(15) . . ?
C14 O4 H4 109.5 . . ?
C3 O7 C1 105.85(17) . . ?
C12 O1 H1 109.5 . . ?
C2 O6 C1 105.49(17) . . ?
C13 O3 H3 109.5 . . ?
C8 N1 C10 107.16(18) . . ?
O1 C12 H12A 109.7 . . ?
O1 C12 H12B 109.7 . . ?
O1 C12 C11 109.64(17) . . ?
H12A C12 H12B 108.2 . . ?
C11 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
O6 C2 C3 109.80(19) . . ?
O6 C2 C7 128.0(2) . . ?
C7 C2 C3 122.2(2) . . ?
O7 C3 C2 109.4(2) . . ?
O7 C3 C4 128.4(2) . . ?
C4 C3 C2 122.2(2) . . ?
O2 C11 C12 111.46(17) . . ?
O2 C11 H11 106.9 . . ?
O2 C11 C13 112.17(17) . . ?
C12 C11 H11 106.9 . . ?
C12 C11 C13 112.11(17) . . ?
C13 C11 H11 106.9 . . ?
O5 C9 H9 110.5 . . ?
O5 C9 C10 103.36(17) . . ?
O5 C9 C14 109.29(17) . . ?
C10 C9 H9 110.5 . . ?
C14 C9 H9 110.5 . . ?
C14 C9 C10 112.49(16) . . ?
C2 C7 H7 121.8 . . ?
C2 C7 C6 116.4(2) . . ?
C6 C7 H7 121.8 . . ?
O5 C8 C6 116.77(18) . . ?
N1 C8 O5 117.9(2) . . ?
N1 C8 C6 125.3(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C6 C5 C4 121.7(2) . . ?
C3 C4 C5 116.4(2) . . ?
C3 C4 H4A 121.8 . . ?
C5 C4 H4A 121.8 . . ?
C7 C6 C8 117.90(19) . . ?
C5 C6 C7 121.1(2) . . ?
C5 C6 C8 121.0(2) . . ?
O2 C10 N1 105.92(16) . . ?
O2 C10 C9 110.75(17) . . ?
O2 C10 H10 111.5 . . ?
N1 C10 C9 105.27(17) . . ?
N1 C10 H10 111.5 . . ?
C9 C10 H10 111.5 . . ?
O4 C14 C9 108.93(16) . . ?
O4 C14 H14 108.8 . . ?
O4 C14 C13 109.61(17) . . ?
C9 C14 H14 108.8 . . ?
C9 C14 C13 111.82(18) . . ?
C13 C14 H14 108.8 . . ?
O3 C13 C11 106.30(16) . . ?
O3 C13 C14 111.12(18) . . ?
O3 C13 H13 109.5 . . ?
C11 C13 H13 109.5 . . ?
C14 C13 C11 110.96(17) . . ?
C14 C13 H13 109.5 . . ?
O7 C1 O6 107.42(18) . . ?
O7 C1 H1A 110.2 . . ?
O7 C1 H1B 110.2 . . ?
O6 C1 H1A 110.2 . . ?
O6 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
