# 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_T1_a
_database_code_depnum_ccdc_archive 'CCDC 1967741'
loop_
_audit_author_name
_audit_author_address
'PRAKASH WARGHUDE'
;IISER PUNE
India
;
_audit_update_record             
;
2019-11-24 deposited with the CCDC.	2020-02-10 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          401
_chemical_formula_moiety         C23H19N3O5
_chemical_formula_sum            'C23 H19 N3 O5'
_chemical_formula_weight         417.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   11.2231(13)
_cell_length_b                   8.1552(9)
_cell_length_c                   11.9835(14)
_cell_angle_alpha                90
_cell_angle_beta                 115.450(5)
_cell_angle_gamma                90
_cell_volume                     990.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9399
_cell_measurement_theta_min      4.09
_cell_measurement_theta_max      65.20

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.832
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6329
_exptl_absorpt_correction_T_max  0.7541
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'Omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23332
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.085
_diffrn_reflns_theta_max         78.820
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4111
_reflns_number_gt                3820
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_max     0.943
_reflns_Friedel_fraction_full    0.987

_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 (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)+(0.0331P)²+0.4564P] 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       0.0182(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1613 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4111
_refine_ls_number_parameters     284
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0954
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
O001 O 0.35668(19) 0.7337(2) 0.13271(18) 0.0234(4) Uani 1 1 d . . . . .
N1 N 0.2254(2) 0.5320(3) 0.1592(2) 0.0212(5) Uani 1 1 d . . . . .
O002 O 0.43513(19) 0.4326(3) 0.03584(17) 0.0235(4) Uani 1 1 d . . . . .
O003 O 0.5317(2) 0.1922(2) 0.37201(19) 0.0261(5) Uani 1 1 d . . . . .
O004 O 0.8153(2) 0.3007(3) 0.3727(2) 0.0300(5) Uani 1 1 d . . . . .
O005 O 0.8179(2) 0.2194(3) 0.1940(2) 0.0371(6) Uani 1 1 d . . . . .
N006 N 0.6052(2) 0.4383(3) 0.4700(2) 0.0221(5) Uani 1 1 d . . . . .
N007 N 0.2181(2) 0.3578(3) 0.1547(2) 0.0224(5) Uani 1 1 d . . . . .
C009 C 0.6398(3) 0.5925(3) 0.4405(3) 0.0209(6) Uani 1 1 d . . . . .
C00A C 0.6142(3) 0.5968(3) 0.3163(3) 0.0195(6) Uani 1 1 d . . . . .
C00B C 0.5569(3) 0.3650(4) 0.0699(3) 0.0243(6) Uani 1 1 d . . . . .
H00B H 0.5880 0.3296 0.0116 0.029 Uiso 1 1 calc R U . . .
C00C C 0.3195(3) 0.3036(3) 0.1428(3) 0.0216(6) Uani 1 1 d . . . . .
C00D C 0.4129(3) 0.4391(4) 0.1461(2) 0.0196(5) Uani 1 1 d . . . . .
C00E C 0.5604(3) 0.3360(3) 0.3713(3) 0.0199(6) Uani 1 1 d . . . . .
C00F C 0.6292(3) 0.3525(3) 0.1922(3) 0.0212(6) Uani 1 1 d . . . . .
C00G C 0.6438(3) 0.7352(3) 0.2667(3) 0.0231(6) Uani 1 1 d . . . . .
H00G H 0.6295 0.7375 0.1827 0.028 Uiso 1 1 calc R U . . .
C00H C 0.3312(3) 0.5913(3) 0.1437(2) 0.0194(6) Uani 1 1 d . . . . .
C00I C 0.5552(3) 0.4339(4) 0.2580(2) 0.0198(5) Uani 1 1 d . . . . .
C00J C 0.1188(3) 0.6219(3) 0.1638(3) 0.0204(6) Uani 1 1 d . . . . .
C00K C 0.6936(3) 0.7252(4) 0.5181(3) 0.0266(6) Uani 1 1 d . . . . .
H00K H 0.7127 0.7204 0.6033 0.032 Uiso 1 1 calc R U . . .
C00L C 0.6949(3) 0.8712(4) 0.3423(3) 0.0273(6) Uani 1 1 d . . . . .
H00L H 0.7137 0.9683 0.3091 0.033 Uiso 1 1 calc R U . . .
C00M C 0.7627(3) 0.2834(3) 0.2489(3) 0.0241(6) Uani 1 1 d . . . . .
C00N C -0.0037(3) 0.8726(4) 0.1328(3) 0.0274(6) Uani 1 1 d . . . . .
H00N H -0.0190 0.9830 0.1049 0.033 Uiso 1 1 calc R U . . .
C00O C 0.0941(3) 0.7824(4) 0.1200(3) 0.0244(6) Uani 1 1 d . . . . .
H00O H 0.1443 0.8297 0.0815 0.029 Uiso 1 1 calc R U . . .
C00P C -0.0793(3) 0.8027(4) 0.1860(3) 0.0306(7) Uani 1 1 d . . . . .
H00P H -0.1452 0.8654 0.1964 0.037 Uiso 1 1 calc R U . . .
C00Q C 0.0405(3) 0.5488(4) 0.2134(3) 0.0275(6) Uani 1 1 d . . . . .
H00Q H 0.0544 0.4377 0.2397 0.033 Uiso 1 1 calc R U . . .
C00R C -0.0582(3) 0.6403(4) 0.2241(3) 0.0328(7) Uani 1 1 d . . . . .
H00R H -0.1122 0.5911 0.2579 0.039 Uiso 1 1 calc R U . . .
C00S C 0.7186(3) 0.8664(4) 0.4656(3) 0.0283(7) Uani 1 1 d . . . . .
H00S H 0.7525 0.9610 0.5155 0.034 Uiso 1 1 calc R U . . .
C00T C 0.6381(3) 0.3828(4) 0.5957(3) 0.0289(7) Uani 1 1 d . . . . .
H00A H 0.6185 0.2655 0.5946 0.043 Uiso 1 1 calc R U . . .
H00C H 0.5857 0.4442 0.6292 0.043 Uiso 1 1 calc R U . . .
H00D H 0.7322 0.4013 0.6476 0.043 Uiso 1 1 calc R U . . .
C00U C 0.3302(3) 0.1284(4) 0.1137(3) 0.0298(7) Uani 1 1 d . . . . .
H00E H 0.4184 0.0873 0.1678 0.045 Uiso 1 1 calc R U . . .
H00F H 0.3156 0.1185 0.0272 0.045 Uiso 1 1 calc R U . . .
H00H H 0.2636 0.0640 0.1268 0.045 Uiso 1 1 calc R U . . .
C00V C 0.9475(3) 0.2360(5) 0.4390(3) 0.0428(9) Uani 1 1 d . . . . .
H00I H 0.9774 0.2541 0.5278 0.064 Uiso 1 1 calc R U . . .
H00J H 1.0072 0.2919 0.4113 0.064 Uiso 1 1 calc R U . . .
H00M H 0.9472 0.1181 0.4228 0.064 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
O001 C00H 1.216(3) . ?
N1 C00H 1.367(4) . ?
N1 C00J 1.425(4) . ?
N1 N007 1.423(3) . ?
O002 C00B 1.364(3) . ?
O002 C00D 1.447(3) . ?
O003 C00E 1.217(3) . ?
O004 C00M 1.348(4) . ?
O004 C00V 1.449(4) . ?
O005 C00M 1.199(4) . ?
N006 C00E 1.356(4) . ?
N006 C009 1.405(4) . ?
N006 C00T 1.460(4) . ?
N007 C00C 1.285(4) . ?
C009 C00K 1.385(4) . ?
C009 C00A 1.390(4) . ?
C00A C00G 1.381(4) . ?
C00A C00I 1.514(4) . ?
C00B C00F 1.340(4) . ?
C00B H00B 0.9500 . ?
C00C C00U 1.488(4) . ?
C00C C00D 1.511(4) . ?
C00D C00H 1.536(4) . ?
C00D C00I 1.585(4) . ?
C00E C00I 1.554(4) . ?
C00F C00M 1.466(4) . ?
C00F C00I 1.522(4) . ?
C00G C00L 1.390(4) . ?
C00G H00G 0.9500 . ?
C00J C00Q 1.388(4) . ?
C00J C00O 1.393(4) . ?
C00K C00S 1.397(5) . ?
C00K H00K 0.9500 . ?
C00L C00S 1.385(5) . ?
C00L H00L 0.9500 . ?
C00N C00P 1.385(5) . ?
C00N C00O 1.384(4) . ?
C00N H00N 0.9500 . ?
C00O H00O 0.9500 . ?
C00P C00R 1.387(5) . ?
C00P H00P 0.9500 . ?
C00Q C00R 1.386(4) . ?
C00Q H00Q 0.9500 . ?
C00R H00R 0.9500 . ?
C00S H00S 0.9500 . ?
C00T H00A 0.9800 . ?
C00T H00C 0.9800 . ?
C00T H00D 0.9800 . ?
C00U H00E 0.9800 . ?
C00U H00F 0.9800 . ?
C00U H00H 0.9800 . ?
C00V H00I 0.9800 . ?
C00V H00J 0.9800 . ?
C00V H00M 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
C00H N1 C00J 128.1(2) . . ?
C00H N1 N007 112.8(2) . . ?
C00J N1 N007 118.6(2) . . ?
C00B O002 C00D 106.6(2) . . ?
C00M O004 C00V 115.3(3) . . ?
C00E N006 C009 111.7(2) . . ?
C00E N006 C00T 122.9(3) . . ?
C009 N006 C00T 124.2(2) . . ?
C00C N007 N1 107.9(2) . . ?
C00K C009 C00A 122.0(3) . . ?
C00K C009 N006 128.2(3) . . ?
C00A C009 N006 109.8(2) . . ?
C00G C00A C009 120.2(3) . . ?
C00G C00A C00I 131.1(3) . . ?
C009 C00A C00I 108.7(2) . . ?
C00F C00B O002 114.6(2) . . ?
C00F C00B H00B 122.7 . . ?
O002 C00B H00B 122.7 . . ?
N007 C00C C00U 121.4(3) . . ?
N007 C00C C00D 112.5(2) . . ?
C00U C00C C00D 125.7(3) . . ?
O002 C00D C00C 109.8(2) . . ?
O002 C00D C00H 110.4(2) . . ?
C00C C00D C00H 100.9(2) . . ?
O002 C00D C00I 105.4(2) . . ?
C00C C00D C00I 116.0(2) . . ?
C00H C00D C00I 114.4(2) . . ?
O003 C00E N006 125.9(3) . . ?
O003 C00E C00I 126.2(3) . . ?
N006 C00E C00I 107.8(2) . . ?
C00B C00F C00M 123.6(3) . . ?
C00B C00F C00I 109.0(2) . . ?
C00M C00F C00I 127.2(2) . . ?
C00A C00G C00L 118.7(3) . . ?
C00A C00G H00G 120.7 . . ?
C00L C00G H00G 120.7 . . ?
O001 C00H N1 127.6(3) . . ?
O001 C00H C00D 127.4(3) . . ?
N1 C00H C00D 104.9(2) . . ?
C00A C00I C00F 113.2(2) . . ?
C00A C00I C00E 101.7(2) . . ?
C00F C00I C00E 113.9(2) . . ?
C00A C00I C00D 116.7(2) . . ?
C00F C00I C00D 98.6(2) . . ?
C00E C00I C00D 113.5(2) . . ?
C00Q C00J C00O 120.3(3) . . ?
C00Q C00J N1 119.5(2) . . ?
C00O C00J N1 120.2(3) . . ?
C009 C00K C00S 117.1(3) . . ?
C009 C00K H00K 121.4 . . ?
C00S C00K H00K 121.4 . . ?
C00S C00L C00G 120.6(3) . . ?
C00S C00L H00L 119.7 . . ?
C00G C00L H00L 119.7 . . ?
O005 C00M O004 124.3(3) . . ?
O005 C00M C00F 125.4(3) . . ?
O004 C00M C00F 110.3(2) . . ?
C00P C00N C00O 120.3(3) . . ?
C00P C00N H00N 119.8 . . ?
C00O C00N H00N 119.8 . . ?
C00N C00O C00J 119.7(3) . . ?
C00N C00O H00O 120.1 . . ?
C00J C00O H00O 120.1 . . ?
C00N C00P C00R 119.5(3) . . ?
C00N C00P H00P 120.3 . . ?
C00R C00P H00P 120.3 . . ?
C00R C00Q C00J 119.1(3) . . ?
C00R C00Q H00Q 120.5 . . ?
C00J C00Q H00Q 120.5 . . ?
C00Q C00R C00P 120.9(3) . . ?
C00Q C00R H00R 119.5 . . ?
C00P C00R H00R 119.5 . . ?
C00L C00S C00K 121.3(3) . . ?
C00L C00S H00S 119.3 . . ?
C00K C00S H00S 119.3 . . ?
N006 C00T H00A 109.5 . . ?
N006 C00T H00C 109.5 . . ?
H00A C00T H00C 109.5 . . ?
N006 C00T H00D 109.5 . . ?
H00A C00T H00D 109.5 . . ?
H00C C00T H00D 109.5 . . ?
C00C C00U H00E 109.5 . . ?
C00C C00U H00F 109.5 . . ?
H00E C00U H00F 109.5 . . ?
C00C C00U H00H 109.5 . . ?
H00E C00U H00H 109.5 . . ?
H00F C00U H00H 109.5 . . ?
O004 C00V H00I 109.5 . . ?
O004 C00V H00J 109.5 . . ?
H00I C00V H00J 109.5 . . ?
O004 C00V H00M 109.5 . . ?
H00I C00V H00M 109.5 . . ?
H00J C00V H00M 109.5 . . ?

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.045


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform and Hexane'
