# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_SS-199_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2007968'
loop_
_audit_author_name
_audit_author_address
'Babulal Das'
;Indian Institute of Technology Guwahati
India
;
_audit_update_record             
;
2020-06-04 deposited with the CCDC.	2020-08-04 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         ?
_chemical_formula_sum            'C21 H16 N2 O4'
_chemical_formula_weight         360.36

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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 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+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   17.6367(15)
_cell_length_b                   13.5661(12)
_cell_length_c                   14.5573(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3483.0(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3074
_cell_measurement_theta_min      1.894
_cell_measurement_theta_max      24.995

_exptl_crystal_description       plates
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            134486
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.894
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3074
_reflns_number_gt                2524
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0657P)²+2.2232P] 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       0.0135(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3074
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1644
_refine_ls_wR_factor_gt          0.1459
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_restrained_S_all      1.180
_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
O2 O 0.36489(11) 0.69466(14) 0.31892(14) 0.0553(5) Uani 1 1 d . . . . .
O4 O 0.31097(10) 0.40611(14) 0.36994(15) 0.0560(6) Uani 1 1 d . . . . .
O1 O 0.33022(12) 0.55773(15) 0.24961(15) 0.0638(6) Uani 1 1 d . . . . .
O3 O 0.55638(11) 0.57120(15) 0.42222(16) 0.0600(6) Uani 1 1 d . . . . .
H3 H 0.5622 0.5139 0.4058 0.090 Uiso 1 1 calc R U . . .
N1 N 0.38912(11) 0.27377(15) 0.35978(14) 0.0410(5) Uani 1 1 d . . . . .
N2 N 0.51166(12) 0.40198(17) 0.36296(15) 0.0451(6) Uani 1 1 d . . . . .
C6 C 0.30623(13) 0.17077(17) 0.45929(19) 0.0413(6) Uani 1 1 d . . . . .
C15 C 0.37493(14) 0.37407(18) 0.36102(16) 0.0385(6) Uani 1 1 d . . . . .
C14 C 0.44329(14) 0.43843(19) 0.35442(16) 0.0388(6) Uani 1 1 d . . . . .
C16 C 0.43614(14) 0.54556(19) 0.35072(16) 0.0390(6) Uani 1 1 d . . . . .
C1 C 0.31836(15) 0.2278(2) 0.5360(2) 0.0501(7) Uani 1 1 d . . . . .
H1 H 0.3377 0.2913 0.5295 0.060 Uiso 1 1 calc R U . . .
C20 C 0.37440(15) 0.59297(19) 0.30301(18) 0.0453(6) Uani 1 1 d . . . . .
C17 C 0.49218(15) 0.6057(2) 0.38810(17) 0.0450(6) Uani 1 1 d . . . . .
C8 C 0.46216(15) 0.2355(2) 0.36626(18) 0.0454(6) Uani 1 1 d . . . . .
C7 C 0.32237(15) 0.2087(2) 0.36402(18) 0.0463(7) Uani 1 1 d . . . . .
H7A H 0.3304 0.1531 0.3233 0.056 Uiso 1 1 calc R U . . .
H7B H 0.2784 0.2446 0.3420 0.056 Uiso 1 1 calc R U . . .
C13 C 0.52295(15) 0.3015(2) 0.36920(19) 0.0479(7) Uani 1 1 d . . . . .
C5 C 0.27581(16) 0.07712(19) 0.4706(2) 0.0538(7) Uani 1 1 d . . . . .
H5 H 0.2670 0.0375 0.4195 0.065 Uiso 1 1 calc R U . . .
C4 C 0.25850(17) 0.0424(2) 0.5577(3) 0.0645(9) Uani 1 1 d . . . . .
H4 H 0.2370 -0.0198 0.5646 0.077 Uiso 1 1 calc R U . . .
C18 C 0.48147(18) 0.7096(2) 0.3928(2) 0.0565(8) Uani 1 1 d . . . . .
H18 H 0.5189 0.7492 0.4185 0.068 Uiso 1 1 calc R U . . .
C19 C 0.41857(19) 0.7502(2) 0.3607(2) 0.0582(8) Uani 1 1 d . . . . .
C2 C 0.30222(17) 0.1920(2) 0.6223(2) 0.0604(8) Uani 1 1 d . . . . .
H2 H 0.3113 0.2311 0.6737 0.073 Uiso 1 1 calc R U . . .
C3 C 0.27274(17) 0.0986(3) 0.6332(2) 0.0649(9) Uani 1 1 d . . . . .
H3A H 0.2627 0.0742 0.6916 0.078 Uiso 1 1 calc R U . . .
C9 C 0.47643(18) 0.1341(2) 0.3727(2) 0.0635(9) Uani 1 1 d . . . . .
H9 H 0.4364 0.0894 0.3726 0.076 Uiso 1 1 calc R U . . .
C12 C 0.59676(17) 0.2655(3) 0.3763(2) 0.0676(9) Uani 1 1 d . . . . .
H12 H 0.6373 0.3094 0.3781 0.081 Uiso 1 1 calc R U . . .
C10 C 0.5503(2) 0.1010(3) 0.3793(3) 0.0788(11) Uani 1 1 d . . . . .
H10 H 0.5597 0.0337 0.3828 0.095 Uiso 1 1 calc R U . . .
C11 C 0.6101(2) 0.1662(3) 0.3807(3) 0.0796(11) Uani 1 1 d . . . . .
H11 H 0.6596 0.1428 0.3846 0.096 Uiso 1 1 calc R U . . .
C21 C 0.3961(3) 0.8564(3) 0.3645(3) 0.0958(14) Uani 1 1 d . . . . .
H21A H 0.4318 0.8921 0.4014 0.144 Uiso 1 1 calc R U . . .
H21B H 0.3464 0.8620 0.3910 0.144 Uiso 1 1 calc R U . . .
H21C H 0.3955 0.8832 0.3034 0.144 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
O2 C19 1.354(3) . ?
O2 C20 1.409(3) . ?
O4 C15 1.216(3) . ?
O1 C20 1.200(3) . ?
O3 C17 1.322(3) . ?
O3 H3 0.8200 . ?
N1 C15 1.384(3) . ?
N1 C8 1.392(3) . ?
N1 C7 1.473(3) . ?
N2 C14 1.309(3) . ?
N2 C13 1.381(4) . ?
C6 C1 1.376(4) . ?
C6 C5 1.389(4) . ?
C6 C7 1.506(4) . ?
C15 C14 1.492(3) . ?
C14 C16 1.460(4) . ?
C16 C17 1.392(3) . ?
C16 C20 1.443(4) . ?
C1 C2 1.377(4) . ?
C1 H1 0.9300 . ?
C17 C18 1.424(4) . ?
C8 C13 1.397(4) . ?
C8 C9 1.402(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C13 C12 1.394(4) . ?
C5 C4 1.387(5) . ?
C5 H5 0.9300 . ?
C4 C3 1.361(5) . ?
C4 H4 0.9300 . ?
C18 C19 1.324(4) . ?
C18 H18 0.9300 . ?
C19 C21 1.495(5) . ?
C2 C3 1.379(4) . ?
C2 H2 0.9300 . ?
C3 H3A 0.9300 . ?
C9 C10 1.381(4) . ?
C9 H9 0.9300 . ?
C12 C11 1.369(5) . ?
C12 H12 0.9300 . ?
C10 C11 1.377(5) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C19 O2 C20 122.4(2) . . ?
C17 O3 H3 109.5 . . ?
C15 N1 C8 122.2(2) . . ?
C15 N1 C7 116.4(2) . . ?
C8 N1 C7 120.9(2) . . ?
C14 N2 C13 120.8(2) . . ?
C1 C6 C5 118.6(3) . . ?
C1 C6 C7 121.7(2) . . ?
C5 C6 C7 119.6(2) . . ?
O4 C15 N1 121.4(2) . . ?
O4 C15 C14 123.2(2) . . ?
N1 C15 C14 115.4(2) . . ?
N2 C14 C16 117.3(2) . . ?
N2 C14 C15 121.1(2) . . ?
C16 C14 C15 121.0(2) . . ?
C17 C16 C20 117.6(2) . . ?
C17 C16 C14 120.5(2) . . ?
C20 C16 C14 121.8(2) . . ?
C2 C1 C6 120.7(3) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
O1 C20 O2 114.8(2) . . ?
O1 C20 C16 128.6(3) . . ?
O2 C20 C16 116.6(2) . . ?
O3 C17 C16 123.2(3) . . ?
O3 C17 C18 116.5(2) . . ?
C16 C17 C18 120.3(3) . . ?
N1 C8 C13 118.2(2) . . ?
N1 C8 C9 122.5(3) . . ?
C13 C8 C9 119.3(3) . . ?
N1 C7 C6 113.2(2) . . ?
N1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
N2 C13 C12 119.0(3) . . ?
N2 C13 C8 121.3(2) . . ?
C12 C13 C8 119.6(3) . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 O2 120.9(3) . . ?
C18 C19 C21 127.6(3) . . ?
O2 C19 C21 111.5(3) . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C11 C10 C9 121.0(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.037

