# 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_356
_audit_block_doi                 10.5517/ccdc.csd.cc24rks8
_database_code_depnum_ccdc_archive 'CCDC 1988860'
loop_
_audit_author_name
_audit_author_address
'Mandapati Bhargava Reddy'
;University of Madras
India
;
_audit_update_record             
;
2020-03-07 deposited with the CCDC.	2020-11-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 N2 O4'
_chemical_formula_sum            'C18 H14 N2 O4'
_chemical_formula_weight         322.31

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           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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'

_cell_length_a                   6.3537(8)
_cell_length_b                   5.0200(6)
_cell_length_c                   23.596(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.173(4)
_cell_angle_gamma                90
_cell_volume                     752.61(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    773
_cell_measurement_theta_min      3.32
_cell_measurement_theta_max      21.56

_exptl_crystal_description       Block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_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            3980
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.318
_diffrn_reflns_theta_max         24.697
_diffrn_reflns_theta_full        24.697
_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 0.782
_diffrn_reflns_point_group_measured_fraction_full 0.782
_reflns_number_total             2005
_reflns_number_gt                1414
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.564
_reflns_Friedel_fraction_max     0.565
_reflns_Friedel_fraction_full    0.565

_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0305P)²+0.0216P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.031(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 472 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.8(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2005
_refine_ls_number_parameters     218
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0730
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.0913
_refine_ls_wR_factor_gt          0.0778
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
C1 C 0.0674(7) 0.3085(10) 0.7859(2) 0.0363(13) Uani 1 1 d . . . . .
C2 C -0.1040(9) 0.1424(11) 0.7789(2) 0.0542(16) Uani 1 1 d . . . . .
H2 H -0.1927 0.1101 0.8095 0.065 Uiso 1 1 calc R U . . .
C3 C -0.1456(10) 0.0241(13) 0.7276(2) 0.0661(19) Uani 1 1 d . . . . .
H3 H -0.2597 -0.0906 0.7236 0.079 Uiso 1 1 calc R U . . .
C4 C -0.0173(10) 0.0765(13) 0.6821(2) 0.0651(19) Uani 1 1 d . . . . .
H4 H -0.0454 -0.0012 0.6471 0.078 Uiso 1 1 calc R U . . .
C5 C 0.1522(9) 0.2435(12) 0.6883(2) 0.0544(16) Uani 1 1 d . . . . .
H5 H 0.2389 0.2759 0.6574 0.065 Uiso 1 1 calc R U . . .
C6 C 0.1969(8) 0.3645(10) 0.7396(2) 0.0394(13) Uani 1 1 d . . . . .
C7 C 0.3860(9) 0.5448(11) 0.7448(2) 0.0527(16) Uani 1 1 d . . . . .
H7A H 0.3888 0.6646 0.7125 0.063 Uiso 1 1 calc R U . . .
H7B H 0.5128 0.4373 0.7435 0.063 Uiso 1 1 calc R U . . .
C8 C 0.3869(9) 0.7090(10) 0.7991(2) 0.0526(15) Uani 1 1 d . . . . .
H8A H 0.5273 0.7771 0.8064 0.063 Uiso 1 1 calc R U . . .
H8B H 0.2921 0.8593 0.7952 0.063 Uiso 1 1 calc R U . . .
C9 C 0.4456(9) 0.4282(11) 0.8844(2) 0.0426(14) Uani 1 1 d . . . . .
C10 C 0.3172(7) 0.2231(11) 0.9119(2) 0.0374(13) Uani 1 1 d . . . . .
C11 C 0.1148(8) 0.4209(11) 0.8432(2) 0.0402(13) Uani 1 1 d . . . . .
H11 H 0.0067 0.5510 0.8537 0.048 Uiso 1 1 calc R U . . .
C12 C 0.3776(8) 0.0707(10) 0.9553(2) 0.0406(14) Uani 1 1 d . . . . .
H12 H 0.5141 0.0988 0.9683 0.049 Uiso 1 1 calc R U . . .
C13 C 0.2575(8) -0.1356(11) 0.9853(2) 0.0396(14) Uani 1 1 d . . . . .
C14 C 0.3532(8) -0.2646(11) 1.0312(2) 0.0450(15) Uani 1 1 d . . . . .
H14 H 0.4896 -0.2173 1.0415 0.054 Uiso 1 1 calc R U . . .
C15 C 0.2514(8) -0.4590(11) 1.0614(2) 0.0460(15) Uani 1 1 d . . . . .
H15 H 0.3165 -0.5429 1.0919 0.055 Uiso 1 1 calc R U . . .
C16 C 0.0499(8) -0.5260(11) 1.0452(2) 0.0415(14) Uani 1 1 d . . . . .
C17 C -0.0495(8) -0.4085(11) 1.0001(2) 0.0476(15) Uani 1 1 d . . . . .
H17 H -0.1845 -0.4607 0.9896 0.057 Uiso 1 1 calc R U . . .
C18 C 0.0547(8) -0.2104(12) 0.9704(2) 0.0429(14) Uani 1 1 d . . . . .
H18 H -0.0122 -0.1267 0.9402 0.051 Uiso 1 1 calc R U . . .
N1 N 0.3205(6) 0.5431(9) 0.84592(16) 0.0446(12) Uani 1 1 d . . . . .
N2 N -0.0602(8) -0.7351(10) 1.07714(19) 0.0538(13) Uani 1 1 d . . . . .
O1 O 0.6315(6) 0.4820(8) 0.89341(16) 0.0564(11) Uani 1 1 d . . . . .
O2 O 0.1258(5) 0.2121(7) 0.88563(13) 0.0450(10) Uani 1 1 d . . . . .
O3 O 0.0333(6) -0.8509(9) 1.11513(18) 0.0743(13) Uani 1 1 d . . . . .
O4 O -0.2442(6) -0.7830(9) 1.06436(19) 0.0771(14) Uani 1 1 d . . . . .


_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
C1 C2 1.381(7) . ?
C1 C6 1.398(7) . ?
C1 C11 1.496(7) . ?
C2 C3 1.374(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.376(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.509(7) . ?
C7 C8 1.525(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.447(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 O1 1.229(6) . ?
C9 N1 1.335(6) . ?
C9 C10 1.466(7) . ?
C10 C12 1.334(6) . ?
C10 O2 1.364(5) . ?
C11 N1 1.445(6) . ?
C11 O2 1.450(6) . ?
C11 H11 0.9800 . ?
C12 C13 1.469(7) . ?
C12 H12 0.9300 . ?
C13 C18 1.386(7) . ?
C13 C14 1.400(6) . ?
C14 C15 1.372(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.370(7) . ?
C16 N2 1.470(7) . ?
C17 C18 1.386(7) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
N2 O3 1.221(5) . ?
N2 O4 1.230(5) . ?

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
C2 C1 C6 119.6(5) . . ?
C2 C1 C11 119.5(5) . . ?
C6 C1 C11 120.9(5) . . ?
C3 C2 C1 121.0(5) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 119.5(6) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 119.9(5) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 121.5(5) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 118.4(5) . . ?
C5 C6 C7 119.7(5) . . ?
C1 C6 C7 121.9(5) . . ?
C6 C7 C8 113.1(5) . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
N1 C8 C7 109.3(4) . . ?
N1 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
O1 C9 N1 126.3(5) . . ?
O1 C9 C10 127.8(5) . . ?
N1 C9 C10 105.9(4) . . ?
C12 C10 O2 125.4(5) . . ?
C12 C10 C9 125.7(5) . . ?
O2 C10 C9 108.9(5) . . ?
N1 C11 O2 103.6(4) . . ?
N1 C11 C1 112.3(4) . . ?
O2 C11 C1 111.1(4) . . ?
N1 C11 H11 109.9 . . ?
O2 C11 H11 109.9 . . ?
C1 C11 H11 109.9 . . ?
C10 C12 C13 128.7(5) . . ?
C10 C12 H12 115.6 . . ?
C13 C12 H12 115.6 . . ?
C18 C13 C14 118.1(5) . . ?
C18 C13 C12 123.6(5) . . ?
C14 C13 C12 118.3(5) . . ?
C15 C14 C13 121.8(5) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 118.0(5) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
C17 C16 C15 122.5(5) . . ?
C17 C16 N2 119.1(5) . . ?
C15 C16 N2 118.4(5) . . ?
C16 C17 C18 118.8(5) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C13 C18 C17 120.8(5) . . ?
C13 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C9 N1 C11 112.5(4) . . ?
C9 N1 C8 126.3(5) . . ?
C11 N1 C8 118.5(4) . . ?
O3 N2 O4 123.1(5) . . ?
O3 N2 C16 119.0(5) . . ?
O4 N2 C16 117.9(5) . . ?
C10 O2 C11 109.0(4) . . ?

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
C6 C1 C2 C3 2.2(8) . . . . ?
C11 C1 C2 C3 -176.4(5) . . . . ?
C1 C2 C3 C4 -1.5(9) . . . . ?
C2 C3 C4 C5 0.8(9) . . . . ?
C3 C4 C5 C6 -0.8(9) . . . . ?
C4 C5 C6 C1 1.4(8) . . . . ?
C4 C5 C6 C7 179.4(5) . . . . ?
C2 C1 C6 C5 -2.1(7) . . . . ?
C11 C1 C6 C5 176.5(5) . . . . ?
C2 C1 C6 C7 179.9(5) . . . . ?
C11 C1 C6 C7 -1.5(7) . . . . ?
C5 C6 C7 C8 167.3(5) . . . . ?
C1 C6 C7 C8 -14.7(7) . . . . ?
C6 C7 C8 N1 41.8(6) . . . . ?
O1 C9 C10 C12 5.5(9) . . . . ?
N1 C9 C10 C12 -175.9(5) . . . . ?
O1 C9 C10 O2 -174.1(5) . . . . ?
N1 C9 C10 O2 4.4(6) . . . . ?
C2 C1 C11 N1 167.9(5) . . . . ?
C6 C1 C11 N1 -10.6(7) . . . . ?
C2 C1 C11 O2 52.4(6) . . . . ?
C6 C1 C11 O2 -126.1(5) . . . . ?
O2 C10 C12 C13 -1.2(8) . . . . ?
C9 C10 C12 C13 179.2(5) . . . . ?
C10 C12 C13 C18 2.3(8) . . . . ?
C10 C12 C13 C14 -178.0(5) . . . . ?
C18 C13 C14 C15 -0.4(8) . . . . ?
C12 C13 C14 C15 179.9(5) . . . . ?
C13 C14 C15 C16 0.2(8) . . . . ?
C14 C15 C16 C17 0.8(8) . . . . ?
C14 C15 C16 N2 179.6(5) . . . . ?
C15 C16 C17 C18 -1.5(8) . . . . ?
N2 C16 C17 C18 179.6(4) . . . . ?
C14 C13 C18 C17 -0.3(7) . . . . ?
C12 C13 C18 C17 179.4(5) . . . . ?
C16 C17 C18 C13 1.3(8) . . . . ?
O1 C9 N1 C11 175.8(5) . . . . ?
C10 C9 N1 C11 -2.7(6) . . . . ?
O1 C9 N1 C8 14.8(9) . . . . ?
C10 C9 N1 C8 -163.8(5) . . . . ?
O2 C11 N1 C9 0.2(6) . . . . ?
C1 C11 N1 C9 -119.8(5) . . . . ?
O2 C11 N1 C8 162.9(4) . . . . ?
C1 C11 N1 C8 42.9(6) . . . . ?
C7 C8 N1 C9 100.8(6) . . . . ?
C7 C8 N1 C11 -59.2(6) . . . . ?
C17 C16 N2 O3 175.5(5) . . . . ?
C15 C16 N2 O3 -3.3(7) . . . . ?
C17 C16 N2 O4 -5.1(7) . . . . ?
C15 C16 N2 O4 176.0(5) . . . . ?
C12 C10 O2 C11 176.0(5) . . . . ?
C9 C10 O2 C11 -4.3(5) . . . . ?
N1 C11 O2 C10 2.6(5) . . . . ?
C1 C11 O2 C10 123.4(5) . . . . ?

_refine_diff_density_max         0.161
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.039



