# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_1e
_database_code_depnum_ccdc_archive 'CCDC 2204731'
loop_
_audit_author_name
_audit_author_address
'xin bao'
;School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology
China
;
_audit_update_record             
;
2022-09-01 deposited with the CCDC.	2023-12-21 downloaded from the CCDC.
;
_audit_creation_date             2022-07-18
_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 H19 N O6'
_chemical_formula_sum            'C14 H19 N O6'
_chemical_formula_weight         297.30
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   17.469(5)
_cell_length_b                   7.599(2)
_cell_length_c                   11.007(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1461.2(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6292
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1294 before and 0.0521 after correction. The Ratio of minimum to maximum transmission is 0.9245. 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    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13781
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.517
_diffrn_reflns_theta_min         2.332
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.900
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2633
_reflns_number_total             3349
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.122
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       0.019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3349
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.028
_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)+(0.0370P)²+0.1001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0781
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_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
2.a Ternary CH refined with riding coordinates:
 N1(H1), C7(H7), C11(H11), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C9(H9A,H9B), C14(H14A,H14B)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_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
O4 O 0.49732(9) 0.9232(2) 0.47116(14) 0.0458(5) Uani 1 1 d . . . . .
O2 O 0.42504(8) 1.0169(2) 0.31994(14) 0.0352(4) Uani 1 1 d . . . . .
O1 O 0.29782(8) 0.9260(2) 0.29847(14) 0.0382(4) Uani 1 1 d . . . . .
O3 O 0.24438(9) 0.7355(2) 0.42498(16) 0.0421(4) Uani 1 1 d . . . . .
N1 N 0.37176(10) 0.7554(2) 0.76615(16) 0.0305(4) Uani 1 1 d . . . . .
H1 H 0.332554 0.755581 0.829840 0.037 Uiso 1 1 calc R . . . .
O6 O 0.39572(10) 0.3888(2) 0.74163(19) 0.0543(5) Uani 1 1 d . . . . .
C6 C 0.30446(12) 0.8141(3) 0.39541(19) 0.0315(5) Uani 1 1 d . . . . .
C4 C 0.43626(12) 0.9095(3) 0.41903(19) 0.0308(5) Uani 1 1 d . . . . .
O5 O 0.38460(14) 0.4304(3) 0.3874(2) 0.0757(7) Uani 1 1 d . . . . .
C5 C 0.37448(12) 0.7995(3) 0.45263(19) 0.0291(5) Uani 1 1 d . . . . .
C7 C 0.38580(12) 0.6554(3) 0.54343(19) 0.0304(5) Uani 1 1 d . . . . .
H7 H 0.440100 0.652501 0.565724 0.036 Uiso 1 1 calc R . . . .
C12 C 0.38776(14) 0.9443(3) 0.7375(2) 0.0404(6) Uani 1 1 d . . . . .
H12A H 0.427211 0.951299 0.676961 0.061 Uiso 1 1 calc GR . . . .
H12B H 0.404312 1.003847 0.809805 0.061 Uiso 1 1 calc GR . . . .
H12C H 0.342036 0.999104 0.707312 0.061 Uiso 1 1 calc GR . . . .
C11 C 0.33831(11) 0.6564(3) 0.6610(2) 0.0296(5) Uani 1 1 d . . . . .
H11 H 0.288117 0.707441 0.642558 0.036 Uiso 1 1 calc R . . . .
C3 C 0.36819(12) 0.9635(3) 0.2345(2) 0.0344(5) Uani 1 1 d . . . . .
C13 C 0.43999(13) 0.6661(3) 0.8190(2) 0.0421(6) Uani 1 1 d . . . . .
H13A H 0.456028 0.726718 0.892228 0.050 Uiso 1 1 calc R . . . .
H13B H 0.481988 0.669186 0.761374 0.050 Uiso 1 1 calc R . . . .
C1 C 0.39398(14) 0.8042(4) 0.1647(2) 0.0456(6) Uani 1 1 d . . . . .
H1A H 0.442035 0.828770 0.125889 0.068 Uiso 1 1 calc GR . . . .
H1B H 0.356429 0.775515 0.104145 0.068 Uiso 1 1 calc GR . . . .
H1C H 0.399947 0.706735 0.219294 0.068 Uiso 1 1 calc GR . . . .
C10 C 0.32661(15) 0.4628(3) 0.6943(2) 0.0440(6) Uani 1 1 d . . . . .
H10 H 0.283025 0.445597 0.749062 0.053 Uiso 1 1 calc R . . . .
C9 C 0.31435(17) 0.3765(4) 0.5723(3) 0.0520(7) Uani 1 1 d . . . . .
H9A H 0.328971 0.253449 0.574749 0.062 Uiso 1 1 calc R . . . .
H9B H 0.261179 0.385023 0.547574 0.062 Uiso 1 1 calc R . . . .
C8 C 0.36495(15) 0.4775(3) 0.4874(3) 0.0446(6) Uani 1 1 d . . . . .
C2 C 0.35240(16) 1.1188(4) 0.1554(3) 0.0506(7) Uani 1 1 d . . . . .
H2A H 0.336565 1.216397 0.204759 0.076 Uiso 1 1 calc GR . . . .
H2B H 0.312474 1.090160 0.098800 0.076 Uiso 1 1 calc GR . . . .
H2C H 0.397991 1.149845 0.111649 0.076 Uiso 1 1 calc GR . . . .
C14 C 0.42008(17) 0.4790(4) 0.8482(3) 0.0566(8) Uani 1 1 d . . . . .
H14A H 0.464452 0.420097 0.882242 0.068 Uiso 1 1 calc R . . . .
H14B H 0.379536 0.476425 0.908422 0.068 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
O4 C4 1.216(3) . ?
O2 C4 1.376(3) . ?
O2 C3 1.426(3) . ?
O1 C6 1.369(3) . ?
O1 C3 1.445(3) . ?
O3 C6 1.251(3) . ?
N1 C12 1.496(3) . ?
N1 C11 1.499(3) . ?
N1 C13 1.490(3) . ?
O6 C10 1.430(3) . ?
O6 C14 1.424(4) . ?
C6 C5 1.380(3) . ?
C4 C5 1.414(3) . ?
O5 C8 1.207(3) . ?
C5 C7 1.496(3) . ?
C7 C11 1.537(3) . ?
C7 C8 1.530(4) . ?
C11 C10 1.530(3) . ?
C3 C1 1.503(4) . ?
C3 C2 1.493(4) . ?
C13 C14 1.499(4) . ?
C10 C9 1.510(4) . ?
C9 C8 1.498(4) . ?

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
C4 O2 C3 116.91(16) . . ?
C6 O1 C3 115.46(16) . . ?
C12 N1 C11 113.06(17) . . ?
C13 N1 C12 111.72(17) . . ?
C13 N1 C11 112.61(18) . . ?
C14 O6 C10 111.3(2) . . ?
O1 C6 C5 118.73(18) . . ?
O3 C6 O1 115.36(19) . . ?
O3 C6 C5 125.9(2) . . ?
O4 C4 O2 116.64(19) . . ?
O4 C4 C5 126.6(2) . . ?
O2 C4 C5 116.68(19) . . ?
C6 C5 C4 120.62(19) . . ?
C6 C5 C7 118.75(19) . . ?
C4 C5 C7 120.44(19) . . ?
C5 C7 C11 119.17(18) . . ?
C5 C7 C8 110.23(19) . . ?
C8 C7 C11 102.46(18) . . ?
N1 C11 C7 116.25(17) . . ?
N1 C11 C10 110.49(19) . . ?
C10 C11 C7 105.58(19) . . ?
O2 C3 O1 109.12(18) . . ?
O2 C3 C1 110.96(18) . . ?
O2 C3 C2 106.7(2) . . ?
O1 C3 C1 110.21(19) . . ?
O1 C3 C2 106.44(19) . . ?
C2 C3 C1 113.2(2) . . ?
N1 C13 C14 109.31(19) . . ?
O6 C10 C11 110.63(19) . . ?
O6 C10 C9 105.9(2) . . ?
C9 C10 C11 102.9(2) . . ?
C8 C9 C10 104.4(2) . . ?
O5 C8 C7 124.2(2) . . ?
O5 C8 C9 125.8(2) . . ?
C9 C8 C7 110.0(2) . . ?
O6 C14 C13 110.4(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
