# 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. 
# 
#######################################################################

data_mo_zyf20210129e_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2103476'
loop_
_audit_author_name
_audit_author_address
'Yuanfei Zhang'
;Nanning Normal University
China
;
_audit_update_record             
;
2021-08-16 deposited with the CCDC.	2021-10-05 downloaded from the CCDC.
;
_audit_creation_date             2021-01-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H14 N2 O5'
_chemical_formula_sum            'C12 H14 N2 O5'
_chemical_formula_weight         266.25
_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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   12.7365(14)
_cell_length_b                   7.8148(9)
_cell_length_c                   24.702(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2458.6(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9014
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.56
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6559
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1417 before and 0.0682 after correction.
The Ratio of minimum to maximum transmission is 0.8791.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            43727
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.821
_diffrn_reflns_theta_min         3.168
_diffrn_ambient_temperature      150.03
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2888
_reflns_number_total             3855
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3855
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0703
_refine_ls_restrained_S_all      1.116
_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)+(0.0500P)²+3.9207P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1651
_refine_ls_wR_factor_ref         0.1794
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.40617(14) 0.3341(2) 0.70329(7) 0.0324(4) Uani 1 1 d . . . . .
O2 O 0.86403(17) 0.6909(3) 0.49310(9) 0.0484(5) Uani 1 1 d . . . . .
O3 O 0.60617(13) 0.3090(2) 0.72404(6) 0.0291(4) Uani 1 1 d . . . . .
O4 O 0.50726(13) 0.7334(2) 0.68339(7) 0.0290(4) Uani 1 1 d . . . . .
H4 H 0.492189 0.758775 0.715507 0.044 Uiso 1 1 calc GR . . . .
O5 O 0.98551(15) 0.6131(3) 0.54911(9) 0.0450(5) Uani 1 1 d . . . . .
N2 N 0.47979(15) 0.3807(2) 0.66298(8) 0.0260(4) Uani 1 1 d . . . . .
N1 N 0.89286(17) 0.6268(3) 0.53591(9) 0.0336(5) Uani 1 1 d . . . . .
C1 C 0.81196(18) 0.5647(3) 0.57397(9) 0.0251(4) Uani 1 1 d . . . . .
C2 C 0.70768(18) 0.5851(3) 0.55957(9) 0.0238(4) Uani 1 1 d . . . . .
H2 H 0.689222 0.638523 0.526348 0.029 Uiso 1 1 calc R . . . .
C3 C 0.63028(17) 0.5258(3) 0.59482(8) 0.0209(4) Uani 1 1 d . . . . .
C4 C 0.51688(17) 0.5343(3) 0.57881(9) 0.0245(4) Uani 1 1 d . . . . .
H4A H 0.503580 0.445055 0.551203 0.029 Uiso 1 1 calc R . . . .
H4B H 0.503715 0.646658 0.561602 0.029 Uiso 1 1 calc R . . . .
C5 C 0.43793(18) 0.5106(3) 0.62497(9) 0.0258(4) Uani 1 1 d . . . . .
C6 C 0.3847(2) 0.1535(3) 0.69902(12) 0.0406(6) Uani 1 1 d . . . . .
H6A H 0.359667 0.127363 0.662425 0.061 Uiso 1 1 calc GR . . . .
H6B H 0.330667 0.121655 0.725436 0.061 Uiso 1 1 calc GR . . . .
H6C H 0.449005 0.088724 0.706311 0.061 Uiso 1 1 calc GR . . . .
C7 C 0.3342(2) 0.4471(4) 0.60036(11) 0.0358(6) Uani 1 1 d . . . . .
H7A H 0.346986 0.341650 0.579921 0.054 Uiso 1 1 calc GR . . . .
H7B H 0.305886 0.534781 0.576056 0.054 Uiso 1 1 calc GR . . . .
H7C H 0.283727 0.424356 0.629407 0.054 Uiso 1 1 calc GR . . . .
C8 C 0.58093(17) 0.3788(3) 0.68165(8) 0.0215(4) Uani 1 1 d . . . . .
C9 C 0.66069(17) 0.4491(3) 0.64352(8) 0.0207(4) Uani 1 1 d . . . . .
C10 C 0.76678(17) 0.4335(3) 0.65726(9) 0.0247(4) Uani 1 1 d . . . . .
H10 H 0.786172 0.383287 0.690820 0.030 Uiso 1 1 calc R . . . .
C11 C 0.84356(18) 0.4912(3) 0.62207(10) 0.0271(5) Uani 1 1 d . . . . .
H11 H 0.915918 0.480519 0.630785 0.032 Uiso 1 1 calc R . . . .
C12 C 0.41648(19) 0.6744(3) 0.65659(10) 0.0317(5) Uani 1 1 d . . . . .
H12A H 0.391168 0.763944 0.631435 0.038 Uiso 1 1 calc R . . . .
H12B H 0.360508 0.652740 0.683543 0.038 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
O1 N2 1.416(3) . ?
O1 C6 1.441(3) . ?
O2 N1 1.226(3) . ?
O3 C8 1.223(3) . ?
O4 H4 0.8400 . ?
O4 C12 1.410(3) . ?
O5 N1 1.229(3) . ?
N2 C5 1.482(3) . ?
N2 C8 1.368(3) . ?
N1 C1 1.477(3) . ?
C1 C2 1.384(3) . ?
C1 C11 1.380(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.395(3) . ?
C3 C4 1.499(3) . ?
C3 C9 1.399(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.531(3) . ?
C5 C7 1.536(3) . ?
C5 C12 1.524(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.490(3) . ?
C9 C10 1.398(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(3) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 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
N2 O1 C6 109.06(19) . . ?
C12 O4 H4 109.5 . . ?
O1 N2 C5 112.57(17) . . ?
C8 N2 O1 112.56(18) . . ?
C8 N2 C5 124.04(18) . . ?
O2 N1 O5 123.5(2) . . ?
O2 N1 C1 118.3(2) . . ?
O5 N1 C1 118.2(2) . . ?
C2 C1 N1 117.9(2) . . ?
C11 C1 N1 118.8(2) . . ?
C11 C1 C2 123.3(2) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.6(2) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C4 120.12(19) . . ?
C2 C3 C9 118.9(2) . . ?
C9 C3 C4 120.83(19) . . ?
C3 C4 H4A 108.4 . . ?
C3 C4 H4B 108.4 . . ?
C3 C4 C5 115.53(18) . . ?
H4A C4 H4B 107.5 . . ?
C5 C4 H4A 108.4 . . ?
C5 C4 H4B 108.4 . . ?
N2 C5 C4 108.55(18) . . ?
N2 C5 C7 109.8(2) . . ?
N2 C5 C12 108.36(19) . . ?
C4 C5 C7 107.99(19) . . ?
C12 C5 C4 113.5(2) . . ?
C12 C5 C7 108.7(2) . . ?
O1 C6 H6A 109.5 . . ?
O1 C6 H6B 109.5 . . ?
O1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 C8 N2 122.7(2) . . ?
O3 C8 C9 121.7(2) . . ?
N2 C8 C9 115.12(18) . . ?
C3 C9 C8 120.86(19) . . ?
C10 C9 C3 120.9(2) . . ?
C10 C9 C8 118.24(19) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H10 119.9 . . ?
C1 C11 C10 118.1(2) . . ?
C1 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
O4 C12 C5 111.61(19) . . ?
O4 C12 H12A 109.3 . . ?
O4 C12 H12B 109.3 . . ?
C5 C12 H12A 109.3 . . ?
C5 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?

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 N2 C5 C4 -172.36(18) . . . . ?
O1 N2 C5 C7 -54.5(2) . . . . ?
O1 N2 C5 C12 64.0(2) . . . . ?
O1 N2 C8 O3 15.0(3) . . . . ?
O1 N2 C8 C9 -172.12(17) . . . . ?
O2 N1 C1 C2 -1.2(3) . . . . ?
O2 N1 C1 C11 179.5(2) . . . . ?
O3 C8 C9 C3 178.9(2) . . . . ?
O3 C8 C9 C10 0.0(3) . . . . ?
O5 N1 C1 C2 178.1(2) . . . . ?
O5 N1 C1 C11 -1.2(3) . . . . ?
N2 C5 C12 O4 56.7(3) . . . . ?
N2 C8 C9 C3 6.0(3) . . . . ?
N2 C8 C9 C10 -172.9(2) . . . . ?
N1 C1 C2 C3 179.45(19) . . . . ?
N1 C1 C11 C10 -179.96(19) . . . . ?
C1 C2 C3 C4 -175.6(2) . . . . ?
C1 C2 C3 C9 0.5(3) . . . . ?
C2 C1 C11 C10 0.8(3) . . . . ?
C2 C3 C4 C5 -164.70(19) . . . . ?
C2 C3 C9 C8 -178.04(19) . . . . ?
C2 C3 C9 C10 0.8(3) . . . . ?
C3 C4 C5 N2 -37.2(3) . . . . ?
C3 C4 C5 C7 -156.2(2) . . . . ?
C3 C4 C5 C12 83.3(2) . . . . ?
C3 C9 C10 C11 -1.3(3) . . . . ?
C4 C3 C9 C8 -2.0(3) . . . . ?
C4 C3 C9 C10 176.8(2) . . . . ?
C4 C5 C12 O4 -63.9(3) . . . . ?
C5 N2 C8 O3 156.5(2) . . . . ?
C5 N2 C8 C9 -30.7(3) . . . . ?
C6 O1 N2 C5 119.6(2) . . . . ?
C6 O1 N2 C8 -94.4(2) . . . . ?
C7 C5 C12 O4 175.9(2) . . . . ?
C8 N2 C5 C4 46.2(3) . . . . ?
C8 N2 C5 C7 164.0(2) . . . . ?
C8 N2 C5 C12 -77.4(3) . . . . ?
C8 C9 C10 C11 177.6(2) . . . . ?
C9 C3 C4 C5 19.4(3) . . . . ?
C9 C10 C11 C1 0.5(3) . . . . ?
C11 C1 C2 C3 -1.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
