# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_d8v18928
_database_code_depnum_ccdc_archive 'CCDC 2039653'
loop_
_audit_author_name
_audit_author_address
'Xiao Zhang'
;Fujian Normal University
China
;
_audit_update_record             
;
2020-10-20 deposited with the CCDC.	2020-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 N2 O6'
_chemical_formula_weight         434.43

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      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   18.1971(18)
_cell_length_b                   12.7997(18)
_cell_length_c                   9.1690(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.325(5)
_cell_angle_gamma                90
_cell_volume                     2086.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4803
_cell_measurement_theta_min      4.582
_cell_measurement_theta_max      36.917

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6118
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            13796
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.291
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3806
_reflns_number_gt                2904
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.962
_reflns_Friedel_fraction_max     0.964
_reflns_Friedel_fraction_full    0.967

_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)+(0.1096P)²+1.2826P] 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       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1143 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.6(9)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3806
_refine_ls_number_parameters     294
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0666
_refine_ls_wR_factor_ref         0.1956
_refine_ls_wR_factor_gt          0.1740
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.005
_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 0.4573(3) 0.0933(4) 0.5370(6) 0.0638(14) Uani 1 1 d . . . . .
O2 O 0.4808(3) 0.2660(5) 0.1889(5) 0.0636(15) Uani 1 1 d . . . . .
O3 O 0.3811(3) 0.2007(5) 0.2584(5) 0.0749(18) Uani 1 1 d . . . . .
O4 O 0.6389(3) 0.1725(5) 0.6773(6) 0.0725(17) Uani 1 1 d . . . . .
O5 O 0.5449(3) 0.2413(4) 0.7666(5) 0.0519(13) Uani 1 1 d . . . . .
O6 O 0.6755(4) 0.2204(5) 0.2708(9) 0.097(2) Uani 1 1 d . . . . .
N1 N 0.4169(3) 0.2585(4) 0.5368(5) 0.0426(12) Uani 1 1 d . . . . .
N2 N 0.6099(3) 0.2940(4) 0.4274(6) 0.0449(13) Uani 1 1 d . . . . .
C1 C 0.3730(4) 0.3455(5) 0.5680(7) 0.0449(15) Uani 1 1 d . . . . .
C2 C 0.3105(4) 0.3487(7) 0.6298(9) 0.0595(19) Uani 1 1 d . . . . .
H2 H 0.2913 0.2882 0.6637 0.071 Uiso 1 1 calc R U . . .
C3 C 0.2768(5) 0.4462(7) 0.6402(10) 0.066(2) Uani 1 1 d . . . . .
H3 H 0.2337 0.4498 0.6795 0.079 Uiso 1 1 calc R U . . .
C4 C 0.3052(4) 0.5348(7) 0.5945(9) 0.064(2) Uani 1 1 d . . . . .
H4 H 0.2834 0.5988 0.6084 0.077 Uiso 1 1 calc R U . . .
C5 C 0.3664(4) 0.5318(6) 0.5272(9) 0.0555(18) Uani 1 1 d . . . . .
H5 H 0.3844 0.5925 0.4913 0.067 Uiso 1 1 calc R U . . .
C6 C 0.3998(4) 0.4370(5) 0.5147(7) 0.0452(15) Uani 1 1 d . . . . .
C7 C 0.4657(3) 0.4119(5) 0.4489(7) 0.0422(14) Uani 1 1 d . . . . .
H7 H 0.4640 0.4456 0.3523 0.051 Uiso 1 1 calc R U . . .
C8 C 0.4681(4) 0.2909(5) 0.4423(7) 0.0415(14) Uani 1 1 d . . . . .
C9 C 0.5551(4) 0.2946(5) 0.5240(7) 0.0424(14) Uani 1 1 d . . . . .
C10 C 0.5453(4) 0.4135(5) 0.5544(7) 0.0419(14) Uani 1 1 d . . . . .
H10 H 0.5450 0.4301 0.6587 0.050 Uiso 1 1 calc R U . . .
C11 C 0.6055(4) 0.4657(5) 0.4969(7) 0.0418(14) Uani 1 1 d . . . . .
C12 C 0.6258(4) 0.5722(6) 0.5064(8) 0.0525(17) Uani 1 1 d . . . . .
H12 H 0.6009 0.6199 0.5553 0.063 Uiso 1 1 calc R U . . .
C13 C 0.6836(4) 0.6034(7) 0.4408(9) 0.061(2) Uani 1 1 d . . . . .
H13 H 0.6975 0.6734 0.4440 0.074 Uiso 1 1 calc R U . . .
C14 C 0.7214(4) 0.5317(7) 0.3702(9) 0.065(2) Uani 1 1 d . . . . .
H14 H 0.7612 0.5541 0.3291 0.078 Uiso 1 1 calc R U . . .
C15 C 0.7009(4) 0.4277(6) 0.3598(8) 0.0526(17) Uani 1 1 d . . . . .
H15 H 0.7261 0.3799 0.3117 0.063 Uiso 1 1 calc R U . . .
C16 C 0.6417(3) 0.3962(6) 0.4228(7) 0.0439(15) Uani 1 1 d . . . . .
C17 C 0.6298(4) 0.2089(7) 0.3505(9) 0.061(2) Uani 1 1 d . . . . .
C18 C 0.5936(5) 0.1062(7) 0.3594(10) 0.068(2) Uani 1 1 d . . . . .
H18A H 0.6300 0.0580 0.4131 0.102 Uiso 1 1 calc R U . . .
H18B H 0.5745 0.0801 0.2604 0.102 Uiso 1 1 calc R U . . .
H18C H 0.5530 0.1139 0.4103 0.102 Uiso 1 1 calc R U . . .
C19 C 0.4187(4) 0.1571(6) 0.5858(7) 0.0499(17) Uani 1 1 d . . . . .
C20 C 0.3758(5) 0.1263(7) 0.7014(9) 0.064(2) Uani 1 1 d . . . . .
H20A H 0.3248 0.1098 0.6537 0.095 Uiso 1 1 calc R U . . .
H20B H 0.3760 0.1830 0.7700 0.095 Uiso 1 1 calc R U . . .
H20C H 0.3989 0.0661 0.7548 0.095 Uiso 1 1 calc R U . . .
C21 C 0.4458(4) 0.2492(5) 0.2827(7) 0.0456(16) Uani 1 1 d . . . . .
C22 C 0.3510(8) 0.1657(9) 0.1050(9) 0.107(4) Uani 1 1 d . . . . .
H22A H 0.3529 0.2222 0.0371 0.160 Uiso 1 1 calc R U . . .
H22B H 0.2998 0.1435 0.0955 0.160 Uiso 1 1 calc R U . . .
H22C H 0.3806 0.1084 0.0818 0.160 Uiso 1 1 calc R U . . .
C23 C 0.5845(4) 0.2261(6) 0.6608(7) 0.0479(16) Uani 1 1 d . . . . .
C24 C 0.5635(5) 0.1754(7) 0.8976(8) 0.066(2) Uani 1 1 d . . . . .
H24A H 0.5529 0.1039 0.8693 0.099 Uiso 1 1 calc R U . . .
H24B H 0.5341 0.1960 0.9680 0.099 Uiso 1 1 calc R U . . .
H24C H 0.6160 0.1827 0.9423 0.099 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 C19 1.223(9) . ?
O2 C21 1.194(8) . ?
O3 C21 1.307(8) . ?
O3 C22 1.466(10) . ?
O4 C23 1.188(9) . ?
O5 C23 1.340(8) . ?
O5 C24 1.447(9) . ?
O6 C17 1.228(9) . ?
N1 C19 1.371(9) . ?
N1 C1 1.434(9) . ?
N1 C8 1.462(8) . ?
N2 C17 1.388(9) . ?
N2 C16 1.434(9) . ?
N2 C9 1.468(8) . ?
C1 C2 1.375(10) . ?
C1 C6 1.396(10) . ?
C2 C3 1.402(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.351(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(10) . ?
C5 H5 0.9300 . ?
C6 C7 1.488(9) . ?
C7 C8 1.550(10) . ?
C7 C10 1.561(8) . ?
C7 H7 0.9800 . ?
C8 C21 1.530(8) . ?
C8 C9 1.600(8) . ?
C9 C23 1.531(10) . ?
C9 C10 1.564(10) . ?
C10 C11 1.474(9) . ?
C10 H10 0.9800 . ?
C11 C16 1.371(9) . ?
C11 C12 1.411(10) . ?
C12 C13 1.378(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(13) . ?
C13 H13 0.9300 . ?
C14 C15 1.381(12) . ?
C14 H14 0.9300 . ?
C15 C16 1.385(9) . ?
C15 H15 0.9300 . ?
C17 C18 1.479(13) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.499(10) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C21 O3 C22 116.5(7) . . ?
C23 O5 C24 116.7(6) . . ?
C19 N1 C1 130.2(5) . . ?
C19 N1 C8 119.3(5) . . ?
C1 N1 C8 110.5(5) . . ?
C17 N2 C16 123.4(5) . . ?
C17 N2 C9 126.5(6) . . ?
C16 N2 C9 110.1(5) . . ?
C2 C1 C6 120.0(7) . . ?
C2 C1 N1 130.6(7) . . ?
C6 C1 N1 109.3(5) . . ?
C1 C2 C3 117.8(7) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 121.6(7) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 120.9(8) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.3(7) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C5 C6 C1 121.2(6) . . ?
C5 C6 C7 129.4(6) . . ?
C1 C6 C7 109.4(6) . . ?
C6 C7 C8 105.3(5) . . ?
C6 C7 C10 117.8(5) . . ?
C8 C7 C10 90.3(5) . . ?
C6 C7 H7 113.6 . . ?
C8 C7 H7 113.6 . . ?
C10 C7 H7 113.6 . . ?
N1 C8 C21 113.2(5) . . ?
N1 C8 C7 103.5(5) . . ?
C21 C8 C7 112.4(5) . . ?
N1 C8 C9 115.1(5) . . ?
C21 C8 C9 119.5(5) . . ?
C7 C8 C9 89.2(5) . . ?
N2 C9 C23 109.1(5) . . ?
N2 C9 C10 103.4(5) . . ?
C23 C9 C10 116.4(5) . . ?
N2 C9 C8 116.7(5) . . ?
C23 C9 C8 120.3(6) . . ?
C10 C9 C8 88.5(5) . . ?
C11 C10 C7 116.5(5) . . ?
C11 C10 C9 104.8(5) . . ?
C7 C10 C9 90.2(5) . . ?
C11 C10 H10 114.2 . . ?
C7 C10 H10 114.2 . . ?
C9 C10 H10 114.2 . . ?
C16 C11 C12 120.7(6) . . ?
C16 C11 C10 110.9(6) . . ?
C12 C11 C10 128.4(6) . . ?
C13 C12 C11 117.9(7) . . ?
C13 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
C12 C13 C14 120.8(8) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C15 C14 C13 121.1(7) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 118.3(8) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C11 C16 C15 121.1(7) . . ?
C11 C16 N2 109.7(5) . . ?
C15 C16 N2 129.2(6) . . ?
O6 C17 N2 119.5(8) . . ?
O6 C17 C18 120.4(7) . . ?
N2 C17 C18 120.1(6) . . ?
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 . . ?
O1 C19 N1 119.2(6) . . ?
O1 C19 C20 120.6(7) . . ?
N1 C19 C20 120.1(7) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 O3 124.3(6) . . ?
O2 C21 C8 123.5(6) . . ?
O3 C21 C8 112.0(5) . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C23 O5 123.7(7) . . ?
O4 C23 C9 124.8(6) . . ?
O5 C23 C9 111.2(6) . . ?
O5 C24 H24A 109.5 . . ?
O5 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O5 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C19 N1 C1 C2 -14.7(12) . . . . ?
C8 N1 C1 C2 168.0(7) . . . . ?
C19 N1 C1 C6 169.5(6) . . . . ?
C8 N1 C1 C6 -7.7(7) . . . . ?
C6 C1 C2 C3 -1.5(10) . . . . ?
N1 C1 C2 C3 -176.9(7) . . . . ?
C1 C2 C3 C4 -1.5(12) . . . . ?
C2 C3 C4 C5 3.9(13) . . . . ?
C3 C4 C5 C6 -3.2(12) . . . . ?
C4 C5 C6 C1 0.2(11) . . . . ?
C4 C5 C6 C7 -179.7(6) . . . . ?
C2 C1 C6 C5 2.2(10) . . . . ?
N1 C1 C6 C5 178.4(7) . . . . ?
C2 C1 C6 C7 -178.0(6) . . . . ?
N1 C1 C6 C7 -1.7(7) . . . . ?
C5 C6 C7 C8 -170.5(7) . . . . ?
C1 C6 C7 C8 9.7(7) . . . . ?
C5 C6 C7 C10 90.8(9) . . . . ?
C1 C6 C7 C10 -89.0(7) . . . . ?
C19 N1 C8 C21 73.6(8) . . . . ?
C1 N1 C8 C21 -108.9(6) . . . . ?
C19 N1 C8 C7 -164.4(5) . . . . ?
C1 N1 C8 C7 13.2(6) . . . . ?
C19 N1 C8 C9 -68.9(7) . . . . ?
C1 N1 C8 C9 108.7(6) . . . . ?
C6 C7 C8 N1 -13.5(6) . . . . ?
C10 C7 C8 N1 105.5(5) . . . . ?
C6 C7 C8 C21 109.0(6) . . . . ?
C10 C7 C8 C21 -131.9(5) . . . . ?
C6 C7 C8 C9 -129.2(5) . . . . ?
C10 C7 C8 C9 -10.1(4) . . . . ?
C17 N2 C9 C23 65.7(8) . . . . ?
C16 N2 C9 C23 -114.0(6) . . . . ?
C17 N2 C9 C10 -169.9(6) . . . . ?
C16 N2 C9 C10 10.4(6) . . . . ?
C17 N2 C9 C8 -74.8(8) . . . . ?
C16 N2 C9 C8 105.5(6) . . . . ?
N1 C8 C9 N2 161.4(5) . . . . ?
C21 C8 C9 N2 21.5(9) . . . . ?
C7 C8 C9 N2 -94.1(6) . . . . ?
N1 C8 C9 C23 25.5(8) . . . . ?
C21 C8 C9 C23 -114.4(7) . . . . ?
C7 C8 C9 C23 130.0(6) . . . . ?
N1 C8 C9 C10 -94.4(6) . . . . ?
C21 C8 C9 C10 125.6(6) . . . . ?
C7 C8 C9 C10 10.1(4) . . . . ?
C6 C7 C10 C11 -135.4(6) . . . . ?
C8 C7 C10 C11 117.0(6) . . . . ?
C6 C7 C10 C9 117.9(6) . . . . ?
C8 C7 C10 C9 10.4(4) . . . . ?
N2 C9 C10 C11 -10.5(6) . . . . ?
C23 C9 C10 C11 109.1(6) . . . . ?
C8 C9 C10 C11 -127.6(5) . . . . ?
N2 C9 C10 C7 107.0(5) . . . . ?
C23 C9 C10 C7 -133.4(6) . . . . ?
C8 C9 C10 C7 -10.0(4) . . . . ?
C7 C10 C11 C16 -90.4(7) . . . . ?
C9 C10 C11 C16 7.3(7) . . . . ?
C7 C10 C11 C12 87.5(8) . . . . ?
C9 C10 C11 C12 -174.7(6) . . . . ?
C16 C11 C12 C13 -0.9(9) . . . . ?
C10 C11 C12 C13 -178.7(6) . . . . ?
C11 C12 C13 C14 -1.1(10) . . . . ?
C12 C13 C14 C15 1.8(11) . . . . ?
C13 C14 C15 C16 -0.5(11) . . . . ?
C12 C11 C16 C15 2.3(9) . . . . ?
C10 C11 C16 C15 -179.6(6) . . . . ?
C12 C11 C16 N2 -179.1(6) . . . . ?
C10 C11 C16 N2 -0.9(7) . . . . ?
C14 C15 C16 C11 -1.6(10) . . . . ?
C14 C15 C16 N2 -180.0(7) . . . . ?
C17 N2 C16 C11 173.8(6) . . . . ?
C9 N2 C16 C11 -6.5(7) . . . . ?
C17 N2 C16 C15 -7.6(10) . . . . ?
C9 N2 C16 C15 172.1(6) . . . . ?
C16 N2 C17 O6 -2.0(11) . . . . ?
C9 N2 C17 O6 178.3(8) . . . . ?
C16 N2 C17 C18 -179.2(7) . . . . ?
C9 N2 C17 C18 1.2(11) . . . . ?
C1 N1 C19 O1 175.3(6) . . . . ?
C8 N1 C19 O1 -7.7(9) . . . . ?
C1 N1 C19 C20 -6.7(10) . . . . ?
C8 N1 C19 C20 170.3(6) . . . . ?
C22 O3 C21 O2 0.0(12) . . . . ?
C22 O3 C21 C8 174.7(8) . . . . ?
N1 C8 C21 O2 -179.2(6) . . . . ?
C7 C8 C21 O2 63.9(9) . . . . ?
C9 C8 C21 O2 -38.6(10) . . . . ?
N1 C8 C21 O3 6.0(8) . . . . ?
C7 C8 C21 O3 -110.8(6) . . . . ?
C9 C8 C21 O3 146.6(6) . . . . ?
C24 O5 C23 O4 -10.0(11) . . . . ?
C24 O5 C23 C9 175.6(6) . . . . ?
N2 C9 C23 O4 -7.4(10) . . . . ?
C10 C9 C23 O4 -123.8(8) . . . . ?
C8 C9 C23 O4 131.4(8) . . . . ?
N2 C9 C23 O5 166.9(5) . . . . ?
C10 C9 C23 O5 50.5(8) . . . . ?
C8 C9 C23 O5 -54.3(8) . . . . ?

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
C24 H24B O2 0.96 2.58 3.530(10) 168.2 1_556
C18 H18C O1 0.96 2.31 3.249(11) 167.4 .
C15 H15 O6 0.93 2.24 2.785(10) 116.9 .
C2 H2 O6 0.93 2.51 3.137(10) 125.1 4_455

_refine_diff_density_max         0.256
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.063

_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_d8v20173
_database_code_depnum_ccdc_archive 'CCDC 2039654'
loop_
_audit_author_name
_audit_author_address
'Xiao Zhang'
;Fujian Normal University
China
;
_audit_update_record             
;
2020-10-20 deposited with the CCDC.	2020-11-20 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 O3'
_chemical_formula_weight         219.23

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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   22.6211(9)
_cell_length_b                   4.8921(2)
_cell_length_c                   9.6732(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1070.48(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    3085
_cell_measurement_theta_min      8.331
_cell_measurement_theta_max      54.808

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             464
_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  0.6534
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(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            4898
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.166
_diffrn_reflns_theta_max         25.959
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.868
_diffrn_reflns_point_group_measured_fraction_full 0.878
_reflns_number_total             1810
_reflns_number_gt                1729
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.648
_reflns_Friedel_fraction_max     0.730
_reflns_Friedel_fraction_full    0.752

_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)+(0.0371P)²+0.1146P] 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       0.029(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 665 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.2(5)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         1810
_refine_ls_number_parameters     148
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0715
_refine_ls_wR_factor_gt          0.0692
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_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 0.50063(6) 0.1694(3) 0.38996(18) 0.0377(4) Uani 1 1 d . . . . .
O2 O 0.67764(7) -0.0311(3) 0.74217(19) 0.0457(4) Uani 1 1 d . . . . .
O3 O 0.61751(6) 0.3201(3) 0.69736(15) 0.0354(4) Uani 1 1 d . . . . .
N1 N 0.59883(7) 0.1648(3) 0.43384(17) 0.0262(4) Uani 1 1 d . . . . .
C1 C 0.61679(8) 0.3632(4) 0.3356(2) 0.0276(5) Uani 1 1 d . . . . .
C2 C 0.58232(9) 0.5219(4) 0.2484(2) 0.0320(5) Uani 1 1 d . . . . .
H2 H 0.5404 0.5082 0.2492 0.038 Uiso 1 1 calc R U . . .
C3 C 0.61110(10) 0.7016(5) 0.1597(2) 0.0402(6) Uani 1 1 d . . . . .
H3 H 0.5885 0.8116 0.0984 0.048 Uiso 1 1 calc R U . . .
C4 C 0.67236(12) 0.7235(5) 0.1589(3) 0.0473(7) Uani 1 1 d . . . . .
H4 H 0.6912 0.8479 0.0976 0.057 Uiso 1 1 calc R U . . .
C5 C 0.70602(10) 0.5645(5) 0.2471(3) 0.0419(6) Uani 1 1 d . . . . .
H5 H 0.7479 0.5788 0.2466 0.050 Uiso 1 1 calc R U . . .
C6 C 0.67815(9) 0.3847(4) 0.3357(2) 0.0318(5) Uani 1 1 d . . . . .
C7 C 0.70479(8) 0.1959(5) 0.4407(2) 0.0367(5) Uani 1 1 d . . . . .
H7A H 0.7278 0.2992 0.5103 0.044 Uiso 1 1 calc R U . . .
H7B H 0.7310 0.0603 0.3959 0.044 Uiso 1 1 calc R U . . .
C8 C 0.65061(8) 0.0537(4) 0.5084(2) 0.0292(5) Uani 1 1 d . . . . .
H8 H 0.6531 -0.1476 0.4914 0.035 Uiso 1 1 calc R U . . .
C9 C 0.64991(8) 0.1052(4) 0.6619(2) 0.0281(5) Uani 1 1 d . . . . .
C10 C 0.61459(10) 0.3795(6) 0.8445(2) 0.0433(6) Uani 1 1 d . . . . .
H10A H 0.5856 0.5247 0.8608 0.065 Uiso 1 1 calc R U . . .
H10B H 0.6535 0.4395 0.8770 0.065 Uiso 1 1 calc R U . . .
H10C H 0.6027 0.2145 0.8947 0.065 Uiso 1 1 calc R U . . .
C11 C 0.54229(8) 0.0706(4) 0.4532(2) 0.0274(4) Uani 1 1 d . . . . .
C12 C 0.53360(9) -0.1539(4) 0.5560(2) 0.0337(5) Uani 1 1 d . . . . .
H12A H 0.5301 -0.0755 0.6488 0.051 Uiso 1 1 calc R U . . .
H12B H 0.5676 -0.2781 0.5530 0.051 Uiso 1 1 calc R U . . .
H12C H 0.4975 -0.2552 0.5335 0.051 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 C11 1.223(2) . ?
O2 C9 1.200(3) . ?
O3 C9 1.326(2) . ?
O3 C10 1.454(3) . ?
N1 C11 1.372(2) . ?
N1 C1 1.418(3) . ?
N1 C8 1.479(2) . ?
C1 C2 1.386(3) . ?
C1 C6 1.392(3) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.499(3) . ?
C7 C8 1.554(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.507(3) . ?
C8 H8 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.495(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C9 O3 C10 115.88(17) . . ?
C11 N1 C1 126.03(17) . . ?
C11 N1 C8 123.26(17) . . ?
C1 N1 C8 110.56(16) . . ?
C2 C1 C6 121.3(2) . . ?
C2 C1 N1 129.04(17) . . ?
C6 C1 N1 109.68(18) . . ?
C1 C2 C3 117.8(2) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 121.3(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C1 120.2(2) . . ?
C5 C6 C7 129.03(18) . . ?
C1 C6 C7 110.79(18) . . ?
C6 C7 C8 104.13(15) . . ?
C6 C7 H7A 110.9 . . ?
C8 C7 H7A 110.9 . . ?
C6 C7 H7B 110.9 . . ?
C8 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
N1 C8 C9 114.25(16) . . ?
N1 C8 C7 104.77(17) . . ?
C9 C8 C7 110.41(17) . . ?
N1 C8 H8 109.1 . . ?
C9 C8 H8 109.1 . . ?
C7 C8 H8 109.1 . . ?
O2 C9 O3 124.20(19) . . ?
O2 C9 C8 122.62(18) . . ?
O3 C9 C8 113.14(17) . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O1 C11 N1 121.2(2) . . ?
O1 C11 C12 121.44(18) . . ?
N1 C11 C12 117.38(17) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 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
C11 N1 C1 C2 6.6(3) . . . . ?
C8 N1 C1 C2 -177.6(2) . . . . ?
C11 N1 C1 C6 -173.46(19) . . . . ?
C8 N1 C1 C6 2.4(2) . . . . ?
C6 C1 C2 C3 0.7(3) . . . . ?
N1 C1 C2 C3 -179.37(19) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 0.3(3) . . . . ?
C4 C5 C6 C7 -179.2(2) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
N1 C1 C6 C5 179.41(18) . . . . ?
C2 C1 C6 C7 178.96(19) . . . . ?
N1 C1 C6 C7 -1.0(2) . . . . ?
C5 C6 C7 C8 178.9(2) . . . . ?
C1 C6 C7 C8 -0.6(2) . . . . ?
C11 N1 C8 C9 -65.7(2) . . . . ?
C1 N1 C8 C9 118.31(19) . . . . ?
C11 N1 C8 C7 173.31(17) . . . . ?
C1 N1 C8 C7 -2.6(2) . . . . ?
C6 C7 C8 N1 1.9(2) . . . . ?
C6 C7 C8 C9 -121.53(18) . . . . ?
C10 O3 C9 O2 -2.8(3) . . . . ?
C10 O3 C9 C8 179.48(19) . . . . ?
N1 C8 C9 O2 157.98(19) . . . . ?
C7 C8 C9 O2 -84.2(3) . . . . ?
N1 C8 C9 O3 -24.3(3) . . . . ?
C7 C8 C9 O3 93.5(2) . . . . ?
C1 N1 C11 O1 -5.1(3) . . . . ?
C8 N1 C11 O1 179.55(19) . . . . ?
C1 N1 C11 C12 175.83(18) . . . . ?
C8 N1 C11 C12 0.5(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
C12 H12A O1 0.98 2.48 3.323(3) 144.5 2_655
C10 H10A O1 0.98 2.47 3.443(3) 170.0 2_665
C7 H7B O2 0.99 2.58 3.463(3) 147.9 4_654
C2 H2 O1 0.95 2.33 2.875(3) 116.2 .

_refine_diff_density_max         0.133
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.026

_shelxl_version_number           2013-4



