# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_DG83R
_audit_block_doi                 10.5517/ccdc.csd.cc228ynz
_database_code_depnum_ccdc_archive 'CCDC 1915231'
loop_
_audit_author_name
_audit_author_address
'E. Suresh'
;Central Salt and Marine Chemicals Research Institute
India
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2019-05-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ORGANIC
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 N2 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         354.39

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.5905(2)
_cell_length_b                   16.0282(4)
_cell_length_c                   11.3851(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.6370(10)
_cell_angle_gamma                90
_cell_volume                     1727.47(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9905
_cell_measurement_theta_min      2.3706
_cell_measurement_theta_max      33.1834
_cell_measurement_temperature    135.(2)

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.381
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.187
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752

_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   'MULTI SCAN'
_exptl_absorpt_process_details   'BRUKER SADABS'


_exptl_absorpt_correction_T_min  0.9640
_exptl_absorpt_correction_T_max  0.9820

_exptl_special_details           
;
;

_diffrn_ambient_temperature      135.(2)

_diffrn_source                   ?
_diffrn_source_type              'MICRO FOCUS TUBE'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            34342
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         33.21
_diffrn_reflns_theta_full        33.21
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_special_details          
;
;

_reflns_number_total             6609
_reflns_number_gt                5586
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1129
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_number_reflns         6609
_refine_ls_number_parameters     323
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    refall
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0546P)²+0.4084P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.195
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_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 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.46953(7) 0.38415(5) 0.02139(7) 0.02583(14) Uani d . . . 1 . .
O O2 0.01055(7) 0.35758(5) -0.05668(7) 0.02956(15) Uani d . . . 1 . .
O O3 0.40705(7) 0.32837(4) 0.24595(6) 0.02294(13) Uani d . . . 1 . .
O O4 0.82449(7) 0.47473(4) 0.66005(6) 0.02397(14) Uani d . . . 1 . .
N N1 0.23419(8) 0.35893(5) -0.04076(7) 0.02129(14) Uani d . . . 1 . .
N N2 0.76833(8) 0.31719(5) 0.68474(7) 0.02076(14) Uani d . . . 1 . .
C C1 0.36182(9) 0.40086(5) 0.02790(8) 0.01988(15) Uani d . . . 1 . .
C C2 0.12996(9) 0.38574(6) -0.00888(8) 0.02242(16) Uani d . . . 1 . .
C C3 0.19033(9) 0.45307(6) 0.09348(9) 0.02566(18) Uani d . . . 1 . .
C C4 0.33269(9) 0.47426(5) 0.09645(8) 0.02025(15) Uani d . . . 1 . .
C C5 0.44916(9) 0.50412(5) 0.22530(8) 0.01735(14) Uani d . . . 1 . .
C C6 0.47577(9) 0.59015(5) 0.23327(8) 0.02077(15) Uani d . . . 1 . .
C C7 0.57599(10) 0.62794(5) 0.34584(9) 0.02176(16) Uani d . . . 1 . .
C C8 0.65647(9) 0.57903(5) 0.45398(8) 0.01951(15) Uani d . . . 1 . .
C C9 0.63354(8) 0.49334(5) 0.44879(7) 0.01553(13) Uani d . . . 1 . .
C C10 0.52835(8) 0.45467(5) 0.33640(7) 0.01522(13) Uani d . . . 1 . .
C C11 0.50356(8) 0.36307(5) 0.34150(7) 0.01620(13) Uani d . . . 1 . .
C C12 0.58846(9) 0.31684(5) 0.45856(8) 0.01782(14) Uani d . . . 1 . .
C C13 0.69147(8) 0.35339(5) 0.56878(7) 0.01659(14) Uani d . . . 1 . .
C C14 0.72441(8) 0.44397(5) 0.56614(7) 0.01654(14) Uani d . . . 1 . .
C C15 0.75449(10) 0.23094(6) 0.71642(8) 0.02225(16) Uani d . . . 1 . .
C C16 0.83637(10) 0.17014(6) 0.67347(9) 0.02427(17) Uani d . . . 1 . .
C C17 0.83424(11) 0.08152(6) 0.72163(9) 0.02683(18) Uani d . . . 1 . .
C C18 0.90956(12) 0.07329(7) 0.87016(10) 0.0303(2) Uani d . . . 1 . .
C C19 0.21316(11) 0.29176(6) -0.13432(9) 0.02616(18) Uani d . . . 1 . .
C C20 0.14117(11) 0.32288(7) -0.27501(9) 0.0296(2) Uani d . . . 1 . .
H H2A 0.8317(15) 0.3482(9) 0.7457(14) 0.032(3) Uiso d . . . 1 . .
H H4 0.3190(14) 0.5195(8) 0.0341(13) 0.028(3) Uiso d . . . 1 . .
H H3A 0.1259(17) 0.5007(10) 0.0721(15) 0.042(4) Uiso d . . . 1 . .
H H3B 0.2028(14) 0.4298(8) 0.1786(13) 0.029(3) Uiso d . . . 1 . .
H H6 0.4229(16) 0.6253(10) 0.1545(15) 0.040(4) Uiso d . . . 1 . .
H H7 0.5872(14) 0.6891(8) 0.3479(13) 0.029(3) Uiso d . . . 1 . .
H H8 0.7295(15) 0.6027(9) 0.5358(14) 0.032(3) Uiso d . . . 1 . .
H H12 0.5645(14) 0.2585(8) 0.4591(12) 0.026(3) Uiso d . . . 1 . .
H H15A 0.6531(14) 0.2159(8) 0.6750(13) 0.026(3) Uiso d . . . 1 . .
H H15B 0.7859(14) 0.2293(8) 0.8091(13) 0.026(3) Uiso d . . . 1 . .
H H16A 0.9368(14) 0.1892(8) 0.7095(13) 0.030(3) Uiso d . . . 1 . .
H H16B 0.7955(16) 0.1698(9) 0.5762(15) 0.037(4) Uiso d . . . 1 . .
H H17A 0.8830(15) 0.0447(9) 0.6864(14) 0.036(4) Uiso d . . . 1 . .
H H17B 0.7344(16) 0.0624(9) 0.6883(15) 0.037(4) Uiso d . . . 1 . .
H H18A 1.0086(18) 0.0911(10) 0.9040(16) 0.048(4) Uiso d . . . 1 . .
H H18B 0.8639(16) 0.1073(9) 0.9114(15) 0.037(4) Uiso d . . . 1 . .
H H18C 0.9072(16) 0.0154(10) 0.8972(15) 0.046(4) Uiso d . . . 1 . .
H H19A 0.3050(17) 0.2692(10) -0.1124(15) 0.043(4) Uiso d . . . 1 . .
H H19B 0.1561(16) 0.2490(9) -0.1169(14) 0.036(4) Uiso d . . . 1 . .
H H20A 0.1972(17) 0.3678(10) -0.2871(15) 0.044(4) Uiso d . . . 1 . .
H H20B 0.0455(17) 0.3465(10) -0.2984(15) 0.042(4) Uiso d . . . 1 . .
H H20C 0.1313(18) 0.2768(11) -0.3360(17) 0.052(5) Uiso d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.2059(11) ?
O2 C2 . 1.2173(11) ?
O3 C11 . 1.2412(9) ?
O4 C14 . 1.2220(9) ?
N1 C2 . 1.3762(12) ?
N1 C1 . 1.3937(11) ?
N1 C19 . 1.4596(11) ?
N2 C13 . 1.3336(10) ?
N2 C15 . 1.4526(11) ?
N2 H2A . 0.873(15) ?
C1 C4 . 1.5179(12) ?
C2 C3 . 1.5045(13) ?
C3 C4 . 1.5310(13) ?
C3 H3A . 0.979(16) ?
C3 H3B . 0.991(14) ?
C4 C5 . 1.5099(11) ?
C4 H4 . 0.978(13) ?
C5 C6 . 1.4022(12) ?
C5 C10 . 1.4072(10) ?
C6 C7 . 1.3843(12) ?
C6 H6 . 0.992(15) ?
C7 C8 . 1.3842(12) ?
C7 H7 . 0.987(14) ?
C8 C9 . 1.3915(11) ?
C8 H8 . 0.981(14) ?
C9 C10 . 1.4086(10) ?
C9 C14 . 1.4780(11) ?
C10 C11 . 1.4971(11) ?
C11 C12 . 1.4351(11) ?
C12 C13 . 1.3713(10) ?
C12 H12 . 0.969(13) ?
C13 C14 . 1.4967(11) ?
C15 C16 . 1.5234(13) ?
C15 H15A . 0.990(13) ?
C15 H15B . 0.954(13) ?
C16 C17 . 1.5264(13) ?
C16 H16A . 1.000(14) ?
C16 H16B . 0.992(15) ?
C17 C18 . 1.5178(14) ?
C17 H17A . 0.980(15) ?
C17 H17B . 0.998(15) ?
C18 H18A . 0.984(17) ?
C18 H18B . 0.978(15) ?
C18 H18C . 0.982(16) ?
C19 C20 . 1.5168(14) ?
C19 H19A . 0.961(16) ?
C19 H19B . 0.990(15) ?
C20 H20A . 0.981(17) ?
C20 H20B . 0.999(16) ?
C20 H20C . 0.986(17) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 C1 . . 113.10(7) ?
C2 N1 C19 . . 123.01(8) ?
C1 N1 C19 . . 123.87(8) ?
C13 N2 C15 . . 125.10(7) ?
C13 N2 H2A . . 116.7(9) ?
C15 N2 H2A . . 118.2(9) ?
O1 C1 N1 . . 124.38(8) ?
O1 C1 C4 . . 128.29(8) ?
N1 C1 C4 . . 107.01(7) ?
O2 C2 N1 . . 124.17(8) ?
O2 C2 C3 . . 127.42(9) ?
N1 C2 C3 . . 108.40(8) ?
C2 C3 C4 . . 104.39(7) ?
C2 C3 H3A . . 111.1(9) ?
C4 C3 H3A . . 113.8(9) ?
C2 C3 H3B . . 108.1(8) ?
C4 C3 H3B . . 111.4(8) ?
H3A C3 H3B . . 108.0(12) ?
C5 C4 C1 . . 118.64(7) ?
C5 C4 C3 . . 117.33(7) ?
C1 C4 C3 . . 104.00(7) ?
C5 C4 H4 . . 105.1(8) ?
C1 C4 H4 . . 101.5(8) ?
C3 C4 H4 . . 108.9(8) ?
C6 C5 C10 . . 118.30(7) ?
C6 C5 C4 . . 115.31(7) ?
C10 C5 C4 . . 126.36(7) ?
C7 C6 C5 . . 122.60(8) ?
C7 C6 H6 . . 118.4(9) ?
C5 C6 H6 . . 119.0(9) ?
C8 C7 C6 . . 119.10(8) ?
C8 C7 H7 . . 121.5(8) ?
C6 C7 H7 . . 119.4(8) ?
C7 C8 C9 . . 119.68(8) ?
C7 C8 H8 . . 122.3(8) ?
C9 C8 H8 . . 118.0(8) ?
C8 C9 C10 . . 121.65(7) ?
C8 C9 C14 . . 117.36(7) ?
C10 C9 C14 . . 120.99(7) ?
C5 C10 C9 . . 118.60(7) ?
C5 C10 C11 . . 122.89(7) ?
C9 C10 C11 . . 118.50(7) ?
O3 C11 C12 . . 120.62(7) ?
O3 C11 C10 . . 119.69(7) ?
C12 C11 C10 . . 119.65(7) ?
C13 C12 C11 . . 122.64(7) ?
C13 C12 H12 . . 120.6(8) ?
C11 C12 H12 . . 116.5(8) ?
N2 C13 C12 . . 127.02(8) ?
N2 C13 C14 . . 113.42(7) ?
C12 C13 C14 . . 119.54(7) ?
O4 C14 C9 . . 122.19(7) ?
O4 C14 C13 . . 119.49(7) ?
C9 C14 C13 . . 118.31(6) ?
N2 C15 C16 . . 113.19(7) ?
N2 C15 H15A . . 108.8(8) ?
C16 C15 H15A . . 110.1(8) ?
N2 C15 H15B . . 106.1(8) ?
C16 C15 H15B . . 111.8(8) ?
H15A C15 H15B . . 106.6(11) ?
C15 C16 C17 . . 112.20(8) ?
C15 C16 H16A . . 109.1(8) ?
C17 C16 H16A . . 108.7(8) ?
C15 C16 H16B . . 109.7(9) ?
C17 C16 H16B . . 109.0(8) ?
H16A C16 H16B . . 108.1(12) ?
C18 C17 C16 . . 113.33(8) ?
C18 C17 H17A . . 107.0(8) ?
C16 C17 H17A . . 108.5(9) ?
C18 C17 H17B . . 109.6(9) ?
C16 C17 H17B . . 109.4(8) ?
H17A C17 H17B . . 108.8(12) ?
C17 C18 H18A . . 110.2(10) ?
C17 C18 H18B . . 111.2(9) ?
H18A C18 H18B . . 108.7(13) ?
C17 C18 H18C . . 110.9(9) ?
H18A C18 H18C . . 108.9(13) ?
H18B C18 H18C . . 106.8(13) ?
N1 C19 C20 . . 111.60(8) ?
N1 C19 H19A . . 106.5(9) ?
C20 C19 H19A . . 111.7(9) ?
N1 C19 H19B . . 105.7(9) ?
C20 C19 H19B . . 112.1(8) ?
H19A C19 H19B . . 109.0(13) ?
C19 C20 H20A . . 109.9(9) ?
C19 C20 H20B . . 112.1(9) ?
H20A C20 H20B . . 106.8(13) ?
C19 C20 H20C . . 110.0(10) ?
H20A C20 H20C . . 109.3(13) ?
H20B C20 H20C . . 108.7(13) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 O1 . . . . 175.34(8) ?
C19 N1 C1 O1 . . . . -3.02(14) ?
C2 N1 C1 C4 . . . . -10.69(10) ?
C19 N1 C1 C4 . . . . 170.95(8) ?
C1 N1 C2 O2 . . . . -179.79(9) ?
C19 N1 C2 O2 . . . . -1.42(14) ?
C1 N1 C2 C3 . . . . -0.45(10) ?
C19 N1 C2 C3 . . . . 177.93(8) ?
O2 C2 C3 C4 . . . . -169.53(9) ?
N1 C2 C3 C4 . . . . 11.15(10) ?
O1 C1 C4 C5 . . . . -37.00(13) ?
N1 C1 C4 C5 . . . . 149.34(8) ?
O1 C1 C4 C3 . . . . -169.48(9) ?
N1 C1 C4 C3 . . . . 16.86(9) ?
C2 C3 C4 C5 . . . . -149.86(7) ?
C2 C3 C4 C1 . . . . -16.63(9) ?
C1 C4 C5 C6 . . . . 129.93(8) ?
C3 C4 C5 C6 . . . . -103.73(9) ?
C1 C4 C5 C10 . . . . -52.00(12) ?
C3 C4 C5 C10 . . . . 74.34(11) ?
C10 C5 C6 C7 . . . . -0.27(13) ?
C4 C5 C6 C7 . . . . 177.96(8) ?
C5 C6 C7 C8 . . . . 1.95(14) ?
C6 C7 C8 C9 . . . . -1.28(13) ?
C7 C8 C9 C10 . . . . -1.03(13) ?
C7 C8 C9 C14 . . . . 178.83(8) ?
C6 C5 C10 C9 . . . . -2.00(12) ?
C4 C5 C10 C9 . . . . 179.98(7) ?
C6 C5 C10 C11 . . . . 176.59(7) ?
C4 C5 C10 C11 . . . . -1.43(13) ?
C8 C9 C10 C5 . . . . 2.69(12) ?
C14 C9 C10 C5 . . . . -177.17(7) ?
C8 C9 C10 C11 . . . . -175.97(7) ?
C14 C9 C10 C11 . . . . 4.18(11) ?
C5 C10 C11 O3 . . . . -1.97(12) ?
C9 C10 C11 O3 . . . . 176.62(8) ?
C5 C10 C11 C12 . . . . -179.82(8) ?
C9 C10 C11 C12 . . . . -1.23(11) ?
O3 C11 C12 C13 . . . . -176.67(8) ?
C10 C11 C12 C13 . . . . 1.16(12) ?
C15 N2 C13 C12 . . . . -1.22(14) ?
C15 N2 C13 C14 . . . . 177.48(8) ?
C11 C12 C13 N2 . . . . 174.72(8) ?
C11 C12 C13 C14 . . . . -3.90(12) ?
C8 C9 C14 O4 . . . . -6.63(12) ?
C10 C9 C14 O4 . . . . 173.22(8) ?
C8 C9 C14 C13 . . . . 173.31(7) ?
C10 C9 C14 C13 . . . . -6.83(11) ?
N2 C13 C14 O4 . . . . 7.75(11) ?
C12 C13 C14 O4 . . . . -173.44(8) ?
N2 C13 C14 C9 . . . . -172.19(7) ?
C12 C13 C14 C9 . . . . 6.61(11) ?
C13 N2 C15 C16 . . . . 83.64(11) ?
N2 C15 C16 C17 . . . . 173.40(7) ?
C15 C16 C17 C18 . . . . -64.87(11) ?
C2 N1 C19 C20 . . . . 82.07(11) ?
C1 N1 C19 C20 . . . . -99.73(10) ?



