# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_dmj8v23138_0m
_database_code_depnum_ccdc_archive 'CCDC 2249384'
loop_
_audit_author_name
_audit_author_address
'Yanzhong Li'
;East China Normal University
China
;
_audit_update_record             
;
2023-03-17 deposited with the CCDC.	2023-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H23 N O4'
_chemical_formula_weight         377.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5232(3)
_cell_length_b                   10.7268(4)
_cell_length_c                   12.1464(4)
_cell_angle_alpha                74.518(2)
_cell_angle_beta                 79.312(2)
_cell_angle_gamma                70.566(2)
_cell_volume                     1003.51(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    7290
_cell_measurement_theta_min      6.609
_cell_measurement_theta_max      109.843

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.441
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5684
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10176
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.303
_diffrn_reflns_theta_max         55.062
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             3732
_reflns_number_gt                3283
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1274P)²+0.0905P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.282(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3732
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0752
_refine_ls_wR_factor_ref         0.1919
_refine_ls_wR_factor_gt          0.1820
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_restrained_S_all      1.142
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.83526(15) 0.04920(14) 0.69987(13) 0.0598(4) Uani 1 1 d . . . . .
O2 O 0.66477(15) 0.00055(14) 0.60800(13) 0.0576(4) Uani 1 1 d . . . . .
O3 O 0.63560(16) 0.33712(12) 0.57766(9) 0.0468(4) Uani 1 1 d . . . . .
O4 O 0.64864(13) 0.38806(10) 0.74390(8) 0.0369(3) Uani 1 1 d . . . . .
N1 N 0.24957(17) 0.23090(13) 0.88913(11) 0.0391(4) Uani 1 1 d . . . . .
C1 C 0.3077(2) 0.09325(16) 0.90254(14) 0.0402(4) Uani 1 1 d . . . . .
C2 C 0.2185(3) 0.01452(19) 0.98659(16) 0.0509(5) Uani 1 1 d . . . . .
H2 H 0.1224 0.0574 1.0304 0.061 Uiso 1 1 calc R U . . .
C3 C 0.2721(3) -0.1236(2) 1.00401(18) 0.0578(5) Uani 1 1 d . . . . .
H3 H 0.2134 -0.1752 1.0606 0.069 Uiso 1 1 calc R U . . .
C4 C 0.4127(3) -0.18867(19) 0.9389(2) 0.0610(6) Uani 1 1 d . . . . .
H4 H 0.4469 -0.2837 0.9515 0.073 Uiso 1 1 calc R U . . .
C5 C 0.5022(3) -0.11632(18) 0.85642(19) 0.0544(5) Uani 1 1 d . . . . .
H5 H 0.5969 -0.1617 0.8131 0.065 Uiso 1 1 calc R U . . .
C6 C 0.4513(2) 0.02722(16) 0.83669(14) 0.0411(4) Uani 1 1 d . . . . .
C7 C 0.54089(19) 0.11026(16) 0.75852(14) 0.0389(4) Uani 1 1 d . . . . .
C8 C 0.48874(18) 0.24761(15) 0.75166(12) 0.0342(4) Uani 1 1 d . . . . .
C9 C 0.33618(18) 0.30582(15) 0.81669(12) 0.0345(4) Uani 1 1 d . . . . .
C10 C 0.26336(18) 0.45510(15) 0.80345(12) 0.0343(4) Uani 1 1 d . . . . .
C11 C 0.2656(2) 0.54348(16) 0.69665(13) 0.0409(4) Uani 1 1 d . . . . .
H11 H 0.3174 0.5092 0.6310 0.049 Uiso 1 1 calc R U . . .
C12 C 0.1924(2) 0.68152(17) 0.68602(15) 0.0482(5) Uani 1 1 d . . . . .
H12 H 0.1955 0.7404 0.6133 0.058 Uiso 1 1 calc R U . . .
C13 C 0.1145(2) 0.73352(17) 0.78145(16) 0.0504(5) Uani 1 1 d . . . . .
H13 H 0.0647 0.8274 0.7740 0.061 Uiso 1 1 calc R U . . .
C14 C 0.1106(2) 0.64587(17) 0.88840(15) 0.0482(5) Uani 1 1 d . . . . .
H14 H 0.0575 0.6804 0.9537 0.058 Uiso 1 1 calc R U . . .
C15 C 0.1844(2) 0.50817(16) 0.89913(13) 0.0409(4) Uani 1 1 d . . . . .
H15 H 0.1814 0.4495 0.9719 0.049 Uiso 1 1 calc R U . . .
C16 C 0.6985(2) 0.04994(16) 0.68713(16) 0.0445(4) Uani 1 1 d . . . . .
C17 C 0.8030(2) -0.0485(2) 0.5246(2) 0.0634(6) Uani 1 1 d . . . . .
H17A H 0.8722 -0.1392 0.5587 0.076 Uiso 1 1 calc R U . . .
H17B H 0.8733 0.0121 0.5016 0.076 Uiso 1 1 calc R U . . .
C18 C 0.7342(3) -0.0531(2) 0.4233(2) 0.0695(6) Uani 1 1 d . . . . .
H18A H 0.8252 -0.0815 0.3656 0.104 Uiso 1 1 calc R U . . .
H18B H 0.6622 0.0362 0.3918 0.104 Uiso 1 1 calc R U . . .
H18C H 0.6699 -0.1171 0.4459 0.104 Uiso 1 1 calc R U . . .
C19 C 0.59775(18) 0.33050(14) 0.67877(12) 0.0337(4) Uani 1 1 d . . . . .
C20 C 0.7661(2) 0.47016(17) 0.69548(14) 0.0423(4) Uani 1 1 d . . . . .
C21 C 0.9280(3) 0.3824(2) 0.6452(2) 0.0655(6) Uani 1 1 d . . . . .
H21A H 0.9668 0.2981 0.7007 0.098 Uiso 1 1 calc R U . . .
H21B H 1.0118 0.4298 0.6265 0.098 Uiso 1 1 calc R U . . .
H21C H 0.9090 0.3630 0.5760 0.098 Uiso 1 1 calc R U . . .
C22 C 0.6840(3) 0.5946(2) 0.60908(19) 0.0639(6) Uani 1 1 d . . . . .
H22A H 0.6570 0.5674 0.5466 0.096 Uiso 1 1 calc R U . . .
H22B H 0.7599 0.6488 0.5790 0.096 Uiso 1 1 calc R U . . .
H22C H 0.5822 0.6476 0.6461 0.096 Uiso 1 1 calc R U . . .
C23 C 0.7937(3) 0.5069(2) 0.80004(18) 0.0627(6) Uani 1 1 d . . . . .
H23A H 0.6868 0.5531 0.8368 0.094 Uiso 1 1 calc R U . . .
H23B H 0.8642 0.5661 0.7773 0.094 Uiso 1 1 calc R U . . .
H23C H 0.8478 0.4251 0.8535 0.094 Uiso 1 1 calc R U . . .


_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 C16 1.201(2) . ?
O2 C16 1.328(2) . ?
O2 C17 1.456(2) . ?
O3 C19 1.1996(18) . ?
O4 C19 1.3272(17) . ?
O4 C20 1.4883(17) . ?
N1 C9 1.320(2) . ?
N1 C1 1.366(2) . ?
C1 C6 1.415(2) . ?
C1 C2 1.418(2) . ?
C2 C3 1.366(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.391(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.372(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.419(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.418(2) . ?
C7 C8 1.374(2) . ?
C7 C16 1.505(2) . ?
C8 C9 1.431(2) . ?
C8 C19 1.504(2) . ?
C9 C10 1.488(2) . ?
C10 C11 1.389(2) . ?
C10 C15 1.391(2) . ?
C11 C12 1.383(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.382(3) . ?
C12 H12 0.9400 . ?
C13 C14 1.388(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.380(2) . ?
C14 H14 0.9400 . ?
C15 H15 0.9400 . ?
C17 C18 1.476(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 H18C 0.9700 . ?
C20 C23 1.504(3) . ?
C20 C22 1.509(3) . ?
C20 C21 1.515(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 H22C 0.9700 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 H23C 0.9700 . ?

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
C16 O2 C17 117.04(14) . . ?
C19 O4 C20 121.56(11) . . ?
C9 N1 C1 118.90(14) . . ?
N1 C1 C6 122.95(14) . . ?
N1 C1 C2 117.76(16) . . ?
C6 C1 C2 119.29(16) . . ?
C3 C2 C1 120.09(19) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.71(17) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 121.07(18) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.83(19) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C7 116.87(14) . . ?
C1 C6 C5 119.01(16) . . ?
C7 C6 C5 124.03(16) . . ?
C8 C7 C6 119.80(15) . . ?
C8 C7 C16 118.92(14) . . ?
C6 C7 C16 121.19(14) . . ?
C7 C8 C9 119.04(14) . . ?
C7 C8 C19 118.48(13) . . ?
C9 C8 C19 122.45(13) . . ?
N1 C9 C8 122.14(14) . . ?
N1 C9 C10 116.18(13) . . ?
C8 C9 C10 121.65(13) . . ?
C11 C10 C15 118.65(14) . . ?
C11 C10 C9 121.61(13) . . ?
C15 C10 C9 119.68(13) . . ?
C12 C11 C10 120.56(14) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 120.46(15) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 119.37(15) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C15 C14 C13 120.18(15) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C10 120.77(14) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
O1 C16 O2 125.25(16) . . ?
O1 C16 C7 123.92(16) . . ?
O2 C16 C7 110.82(13) . . ?
O2 C17 C18 108.80(16) . . ?
O2 C17 H17A 109.9 . . ?
C18 C17 H17A 109.9 . . ?
O2 C17 H17B 109.9 . . ?
C18 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 O4 126.64(13) . . ?
O3 C19 C8 123.46(13) . . ?
O4 C19 C8 109.84(11) . . ?
O4 C20 C23 102.44(13) . . ?
O4 C20 C22 109.70(14) . . ?
C23 C20 C22 111.38(17) . . ?
O4 C20 C21 109.22(14) . . ?
C23 C20 C21 110.57(17) . . ?
C22 C20 C21 112.98(17) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C9 N1 C1 C6 -4.2(2) . . . . ?
C9 N1 C1 C2 175.78(15) . . . . ?
N1 C1 C2 C3 -179.50(15) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
N1 C1 C6 C7 3.5(2) . . . . ?
C2 C1 C6 C7 -176.57(15) . . . . ?
N1 C1 C6 C5 -179.86(15) . . . . ?
C2 C1 C6 C5 0.1(2) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C4 C5 C6 C7 176.08(17) . . . . ?
C1 C6 C7 C8 1.5(2) . . . . ?
C5 C6 C7 C8 -175.02(15) . . . . ?
C1 C6 C7 C16 177.99(14) . . . . ?
C5 C6 C7 C16 1.5(3) . . . . ?
C6 C7 C8 C9 -5.3(2) . . . . ?
C16 C7 C8 C9 178.07(13) . . . . ?
C6 C7 C8 C19 172.66(13) . . . . ?
C16 C7 C8 C19 -3.9(2) . . . . ?
C1 N1 C9 C8 0.1(2) . . . . ?
C1 N1 C9 C10 178.17(12) . . . . ?
C7 C8 C9 N1 4.7(2) . . . . ?
C19 C8 C9 N1 -173.20(13) . . . . ?
C7 C8 C9 C10 -173.26(13) . . . . ?
C19 C8 C9 C10 8.8(2) . . . . ?
N1 C9 C10 C11 -138.57(15) . . . . ?
C8 C9 C10 C11 39.5(2) . . . . ?
N1 C9 C10 C15 38.6(2) . . . . ?
C8 C9 C10 C15 -143.27(15) . . . . ?
C15 C10 C11 C12 0.7(2) . . . . ?
C9 C10 C11 C12 177.91(15) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 C10 -0.1(3) . . . . ?
C11 C10 C15 C14 -0.3(2) . . . . ?
C9 C10 C15 C14 -177.62(14) . . . . ?
C17 O2 C16 O1 -5.2(3) . . . . ?
C17 O2 C16 C7 173.77(16) . . . . ?
C8 C7 C16 O1 65.1(2) . . . . ?
C6 C7 C16 O1 -111.5(2) . . . . ?
C8 C7 C16 O2 -113.88(16) . . . . ?
C6 C7 C16 O2 69.6(2) . . . . ?
C16 O2 C17 C18 -160.22(18) . . . . ?
C20 O4 C19 O3 -0.7(2) . . . . ?
C20 O4 C19 C8 176.62(12) . . . . ?
C7 C8 C19 O3 59.7(2) . . . . ?
C9 C8 C19 O3 -122.40(17) . . . . ?
C7 C8 C19 O4 -117.78(14) . . . . ?
C9 C8 C19 O4 60.15(18) . . . . ?
C19 O4 C20 C23 -177.14(14) . . . . ?
C19 O4 C20 C22 64.46(19) . . . . ?
C19 O4 C20 C21 -59.87(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C22 H22A O3 0.97 2.46 3.053(2) 119.2 .
C21 H21C O3 0.97 2.43 2.982(2) 115.5 .

_refine_diff_density_max         0.475
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.099

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v23248_0m
_database_code_depnum_ccdc_archive 'CCDC 2264615'
loop_
_audit_author_name
_audit_author_address
'Qiongwen Kang'
;East China Normal University
China
;
_audit_update_record             
;
2023-05-22 deposited with the CCDC.	2023-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 N O4'
_chemical_formula_weight         235.23

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'

_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'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   6.8757(8)
_cell_length_b                   15.6611(17)
_cell_length_c                   22.392(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2411.2(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2746
_cell_measurement_theta_min      5.511
_cell_measurement_theta_max      48.043

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6037
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14179
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.756
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             2120
_reflns_number_gt                1200
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1851P)²+6.9528P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2120
_refine_ls_number_parameters     176
_refine_ls_number_restraints     40
_refine_ls_R_factor_all          0.2042
_refine_ls_R_factor_gt           0.1405
_refine_ls_wR_factor_ref         0.4327
_refine_ls_wR_factor_gt          0.3813
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.123
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.001

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 0.2418(9) 0.8240(5) 0.6537(3) 0.094(2) Uani 1 1 d . . . . .
O2 O 0.5525(11) 0.8551(4) 0.7339(3) 0.092(2) Uani 1 1 d . . . . .
H2 H 0.6250 0.8425 0.7616 0.138 Uiso 1 1 calc R U . . .
O3 O 0.4961(9) 0.6924(4) 0.7642(2) 0.091(2) Uani 1 1 d . . . . .
O4 O 0.5372(11) 0.6483(3) 0.6710(3) 0.098(2) Uani 1 1 d D . . . .
N1 N 0.7530(9) 0.8010(4) 0.6542(3) 0.0687(18) Uani 1 1 d . . . . .
H1 H 0.8678 0.7929 0.6683 0.082 Uiso 1 1 calc R U . . .
C1 C 0.7117(12) 0.8210(5) 0.5961(4) 0.068(2) Uani 1 1 d . . . . .
C2 C 0.8469(14) 0.8280(6) 0.5490(4) 0.080(3) Uani 1 1 d . . . . .
H2A H 0.9784 0.8169 0.5547 0.096 Uiso 1 1 calc R U . . .
C3 C 0.7756(17) 0.8519(6) 0.4948(4) 0.092(3) Uani 1 1 d . . . . .
H3 H 0.8629 0.8570 0.4633 0.111 Uiso 1 1 calc R U . . .
C4 C 0.5745(18) 0.8695(6) 0.4832(4) 0.089(3) Uani 1 1 d . . . . .
C5 C 0.4545(16) 0.8623(6) 0.5305(4) 0.080(3) Uani 1 1 d . . . . .
H5 H 0.3240 0.8760 0.5251 0.096 Uiso 1 1 calc R U . . .
C6 C 0.5135(10) 0.8360(5) 0.5860(3) 0.0554(18) Uani 1 1 d . . . . .
C7 C 0.4145(16) 0.8202(5) 0.6411(4) 0.077(2) Uani 1 1 d . . . . .
C8 C 0.5692(13) 0.7954(5) 0.6893(3) 0.071(2) Uani 1 1 d . . . . .
C9 C 0.5270(12) 0.7074(5) 0.7118(3) 0.071(2) Uani 1 1 d . . . . .
C10 C 0.531(3) 0.5586(9) 0.6935(8) 0.098(5) Uani 0.6 1 d D U P A 1
H10A H 0.4264 0.5510 0.7219 0.117 Uiso 0.6 1 calc R U P A 1
H10B H 0.6534 0.5433 0.7125 0.117 Uiso 0.6 1 calc R U P A 1
C11 C 0.498(3) 0.5057(10) 0.6378(7) 0.099(5) Uani 0.6 1 d D U P A 1
H11A H 0.3687 0.5160 0.6230 0.149 Uiso 0.6 1 calc R U P A 1
H11B H 0.5119 0.4463 0.6472 0.149 Uiso 0.6 1 calc R U P A 1
H11C H 0.5910 0.5214 0.6078 0.149 Uiso 0.6 1 calc R U P A 1
C10' C 0.457(4) 0.5625(11) 0.6858(15) 0.097(5) Uani 0.4 1 d D U P A 2
H10C H 0.3349 0.5517 0.6654 0.117 Uiso 0.4 1 calc R U P A 2
H10D H 0.4385 0.5554 0.7285 0.117 Uiso 0.4 1 calc R U P A 2
C11' C 0.619(4) 0.5064(15) 0.6624(11) 0.103(5) Uani 0.4 1 d D U P A 2
H11D H 0.6090 0.5024 0.6197 0.155 Uiso 0.4 1 calc R U P A 2
H11E H 0.6075 0.4504 0.6796 0.155 Uiso 0.4 1 calc R U P A 2
H11F H 0.7419 0.5307 0.6731 0.155 Uiso 0.4 1 calc R U P A 2
C12 C 0.5093(15) 0.8980(8) 0.4220(4) 0.113(4) Uani 1 1 d . . . . .
H12A H 0.3703 0.9036 0.4214 0.169 Uiso 1 1 calc R U . . .
H12B H 0.5486 0.8564 0.3928 0.169 Uiso 1 1 calc R U . . .
H12C H 0.5677 0.9521 0.4127 0.169 Uiso 1 1 calc R U . . .


_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 C7 1.222(11) . ?
O2 C8 1.373(9) . ?
O2 H2 0.8200 . ?
O3 C9 1.215(9) . ?
O4 C9 1.304(9) . ?
O4 C10' 1.491(18) . ?
O4 C10 1.492(14) . ?
N1 C1 1.367(9) . ?
N1 C8 1.492(10) . ?
N1 H1 0.8600 . ?
C1 C6 1.402(10) . ?
C1 C2 1.410(12) . ?
C2 C3 1.361(12) . ?
C2 H2A 0.9300 . ?
C3 C4 1.434(15) . ?
C3 H3 0.9300 . ?
C4 C5 1.347(13) . ?
C4 C12 1.511(13) . ?
C5 C6 1.371(11) . ?
C5 H5 0.9300 . ?
C6 C7 1.431(12) . ?
C7 C8 1.565(12) . ?
C8 C9 1.494(11) . ?
C10 C11 1.515(17) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C10' C11' 1.511(19) . ?
C10' H10C 0.9700 . ?
C10' H10D 0.9700 . ?
C11' H11D 0.9600 . ?
C11' H11E 0.9600 . ?
C11' H11F 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C8 O2 H2 109.5 . . ?
C9 O4 C10' 117.6(13) . . ?
C9 O4 C10 115.5(9) . . ?
C1 N1 C8 109.9(6) . . ?
C1 N1 H1 125.1 . . ?
C8 N1 H1 125.1 . . ?
N1 C1 C6 113.2(7) . . ?
N1 C1 C2 126.3(8) . . ?
C6 C1 C2 120.4(8) . . ?
C3 C2 C1 116.9(9) . . ?
C3 C2 H2A 121.6 . . ?
C1 C2 H2A 121.6 . . ?
C2 C3 C4 124.1(9) . . ?
C2 C3 H3 117.9 . . ?
C4 C3 H3 117.9 . . ?
C5 C4 C3 115.6(9) . . ?
C5 C4 C12 123.8(11) . . ?
C3 C4 C12 120.5(9) . . ?
C4 C5 C6 123.8(10) . . ?
C4 C5 H5 118.1 . . ?
C6 C5 H5 118.1 . . ?
C5 C6 C1 119.0(8) . . ?
C5 C6 C7 133.9(8) . . ?
C1 C6 C7 107.1(7) . . ?
O1 C7 C6 130.8(8) . . ?
O1 C7 C8 120.8(8) . . ?
C6 C7 C8 108.4(8) . . ?
O2 C8 N1 114.5(7) . . ?
O2 C8 C9 111.6(7) . . ?
N1 C8 C9 113.4(7) . . ?
O2 C8 C7 106.0(7) . . ?
N1 C8 C7 101.3(6) . . ?
C9 C8 C7 109.2(7) . . ?
O3 C9 O4 123.3(8) . . ?
O3 C9 C8 122.5(7) . . ?
O4 C9 C8 114.1(7) . . ?
O4 C10 C11 103.9(13) . . ?
O4 C10 H10A 111.0 . . ?
C11 C10 H10A 111.0 . . ?
O4 C10 H10B 111.0 . . ?
C11 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C10' C11' 100.0(17) . . ?
O4 C10' H10C 111.8 . . ?
C11' C10' H10C 111.8 . . ?
O4 C10' H10D 111.8 . . ?
C11' C10' H10D 111.8 . . ?
H10C C10' H10D 109.5 . . ?
C10' C11' H11D 109.5 . . ?
C10' C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
C10' C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C8 N1 C1 C6 3.8(9) . . . . ?
C8 N1 C1 C2 -176.9(7) . . . . ?
N1 C1 C2 C3 -177.6(8) . . . . ?
C6 C1 C2 C3 1.6(12) . . . . ?
C1 C2 C3 C4 -0.3(14) . . . . ?
C2 C3 C4 C5 0.9(14) . . . . ?
C2 C3 C4 C12 178.3(10) . . . . ?
C3 C4 C5 C6 -3.1(14) . . . . ?
C12 C4 C5 C6 179.6(9) . . . . ?
C4 C5 C6 C1 4.5(13) . . . . ?
C4 C5 C6 C7 -176.9(9) . . . . ?
N1 C1 C6 C5 175.6(7) . . . . ?
C2 C1 C6 C5 -3.7(12) . . . . ?
N1 C1 C6 C7 -3.3(9) . . . . ?
C2 C1 C6 C7 177.4(7) . . . . ?
C5 C6 C7 O1 2.2(16) . . . . ?
C1 C6 C7 O1 -179.1(9) . . . . ?
C5 C6 C7 C8 -177.3(8) . . . . ?
C1 C6 C7 C8 1.5(8) . . . . ?
C1 N1 C8 O2 -116.1(7) . . . . ?
C1 N1 C8 C9 114.4(7) . . . . ?
C1 N1 C8 C7 -2.5(8) . . . . ?
O1 C7 C8 O2 -59.1(11) . . . . ?
C6 C7 C8 O2 120.4(7) . . . . ?
O1 C7 C8 N1 -178.9(8) . . . . ?
C6 C7 C8 N1 0.6(8) . . . . ?
O1 C7 C8 C9 61.2(10) . . . . ?
C6 C7 C8 C9 -119.3(7) . . . . ?
C10' O4 C9 O3 16.6(18) . . . . ?
C10 O4 C9 O3 -6.9(15) . . . . ?
C10' O4 C9 C8 -167.1(15) . . . . ?
C10 O4 C9 C8 169.5(11) . . . . ?
O2 C8 C9 O3 -4.9(12) . . . . ?
N1 C8 C9 O3 126.1(9) . . . . ?
C7 C8 C9 O3 -121.7(9) . . . . ?
O2 C8 C9 O4 178.8(8) . . . . ?
N1 C8 C9 O4 -50.2(10) . . . . ?
C7 C8 C9 O4 61.9(10) . . . . ?
C9 O4 C10 C11 167.1(13) . . . . ?
C10' O4 C10 C11 66(4) . . . . ?
C9 O4 C10' C11' -134.9(18) . . . . ?
C10 O4 C10' C11' -45(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11B O1 0.96 2.59 3.308(18) 131.3 8_655
N1 H1 O3 0.86 2.35 3.005(9) 132.8 6_657
N1 H1 O1 0.86 2.64 3.380(10) 145.3 1_655
O2 H2 O1 0.82 2.08 2.874(9) 163.3 6_657
O2 H2 O1 0.82 2.08 2.874(9) 163.3 6_657
N1 H1 O1 0.86 2.64 3.380(10) 145.3 1_655
N1 H1 O3 0.86 2.35 3.005(9) 132.8 6_657
C11 H11B O1 0.96 2.59 3.308(18) 131.3 8_655

_refine_diff_density_max         0.578
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.081

_shelxl_version_number           2013-4

