# Electronic Supplementary Material (ESI) for ChemComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1973104'
loop_
_audit_author_name
_audit_author_address
'Akash Tathe'
;Indian Institute of Science Education and Research Bhopal
India
;
_audit_update_record             
;
2019-12-19 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 N O4'
_chemical_formula_sum            'C19 H19 N O4'
_chemical_formula_weight         325.35

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.7313(4)
_cell_length_b                   8.2310(4)
_cell_length_c                   13.2902(7)
_cell_angle_alpha                81.614(2)
_cell_angle_beta                 79.942(2)
_cell_angle_gamma                89.931(2)
_cell_volume                     823.58(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    7054
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      29.49

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             344.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(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            16074
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.502
_diffrn_reflns_theta_max         27.868
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3916
_reflns_number_gt                2966
_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 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)+(0.0612P)²+0.3563P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3916
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.1202
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.78777(15) 0.94693(14) 0.18463(9) 0.0291(3) Uani 1 1 d . . . . .
O002 O 0.70785(16) 0.88162(13) -0.03906(9) 0.0301(3) Uani 1 1 d . . . . .
O003 O 0.52173(16) 0.46712(15) 0.22721(9) 0.0326(3) Uani 1 1 d . . . . .
O004 O 0.03342(17) 0.58849(17) 0.62825(10) 0.0406(3) Uani 1 1 d . . . . .
N005 N 0.59944(17) 0.70306(16) 0.11057(10) 0.0231(3) Uani 1 1 d . . . . .
C006 C 0.7557(2) 0.58688(18) -0.02356(12) 0.0218(3) Uani 1 1 d . . . . .
C007 C 0.6952(2) 0.46043(19) 0.05602(12) 0.0226(3) Uani 1 1 d . . . . .
C008 C 0.5945(2) 0.53385(19) 0.14334(12) 0.0233(3) Uani 1 1 d . . . . .
C009 C 0.6371(2) 0.86449(19) 0.24824(12) 0.0238(3) Uani 1 1 d . . . . .
H009 H 0.674450 0.761117 0.287325 0.029 Uiso 1 1 calc R U . . .
C00A C 0.6908(2) 0.74459(19) 0.00937(12) 0.0225(3) Uani 1 1 d . . . . .
C00B C 0.8616(2) 0.5573(2) -0.11328(13) 0.0282(4) Uani 1 1 d . . . . .
H00B H 0.903108 0.644079 -0.167555 0.034 Uiso 1 1 calc R U . . .
C00C C 0.7366(2) 0.2989(2) 0.04823(14) 0.0295(4) Uani 1 1 d . . . . .
H00C H 0.693754 0.212448 0.102406 0.035 Uiso 1 1 calc R U . . .
C00D C 0.9054(2) 0.3948(2) -0.12113(15) 0.0341(4) Uani 1 1 d . . . . .
H00D H 0.979097 0.370327 -0.181800 0.041 Uiso 1 1 calc R U . . .
C00E C 0.8435(2) 0.2682(2) -0.04219(15) 0.0344(4) Uani 1 1 d . . . . .
H00E H 0.874664 0.158471 -0.050047 0.041 Uiso 1 1 calc R U . . .
C00F C 0.5412(2) 0.9702(2) 0.32535(13) 0.0300(4) Uani 1 1 d . . . . .
H00A H 0.628169 1.018188 0.359895 0.036 Uiso 1 1 calc R U . . .
H00F H 0.484930 1.061825 0.287229 0.036 Uiso 1 1 calc R U . . .
C00G C 0.2259(2) 0.8973(2) 0.40779(14) 0.0305(4) Uani 1 1 d . . . . .
H00G H 0.190224 0.978005 0.357252 0.037 Uiso 1 1 calc R U . . .
C00H C 0.5189(2) 0.8202(2) 0.17564(13) 0.0264(4) Uani 1 1 d . . . . .
H00H H 0.406460 0.772671 0.216826 0.032 Uiso 1 1 calc R U . . .
H00I H 0.492422 0.921241 0.131269 0.032 Uiso 1 1 calc R U . . .
C00I C 0.0977(2) 0.8064(2) 0.48065(14) 0.0320(4) Uani 1 1 d . . . . .
H00Z H -0.023330 0.825047 0.479649 0.038 Uiso 1 1 calc R U . . .
C00J C 0.4030(2) 0.8742(2) 0.40641(12) 0.0260(4) Uani 1 1 d . . . . .
C00K C 0.3256(2) 0.6650(2) 0.55622(13) 0.0323(4) Uani 1 1 d . . . . .
H00K H 0.361148 0.585779 0.607631 0.039 Uiso 1 1 calc R U . . .
C00L C 0.1481(2) 0.6886(2) 0.55456(12) 0.0293(4) Uani 1 1 d . . . . .
C00M C 0.4503(2) 0.7568(2) 0.48312(13) 0.0303(4) Uani 1 1 d . . . . .
H00M H 0.571244 0.739643 0.485028 0.036 Uiso 1 1 calc R U . . .
C00N C 0.9280(2) 0.9701(2) 0.23773(15) 0.0363(4) Uani 1 1 d . . . . .
H00J H 1.026631 1.027329 0.189160 0.054 Uiso 1 1 calc R U . . .
H00L H 0.888250 1.035814 0.292838 0.054 Uiso 1 1 calc R U . . .
H00N H 0.965955 0.862982 0.267843 0.054 Uiso 1 1 calc R U . . .
C00O C -0.1488(3) 0.5985(3) 0.62128(16) 0.0425(5) Uani 1 1 d . . . . .
H00O H -0.217220 0.522022 0.677547 0.064 Uiso 1 1 calc R U . . .
H00P H -0.187739 0.710715 0.626761 0.064 Uiso 1 1 calc R U . . .
H00Q H -0.166433 0.569592 0.554750 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 C00N 1.420(2) . ?
O001 C009 1.4222(19) . ?
O002 C00A 1.2095(19) . ?
O003 C008 1.2099(19) . ?
O004 C00L 1.374(2) . ?
O004 C00O 1.430(2) . ?
N005 C008 1.396(2) . ?
N005 C00A 1.400(2) . ?
N005 C00H 1.456(2) . ?
C006 C00B 1.376(2) . ?
C006 C007 1.389(2) . ?
C006 C00A 1.488(2) . ?
C007 C00C 1.381(2) . ?
C007 C008 1.485(2) . ?
C009 C00H 1.520(2) . ?
C009 C00F 1.533(2) . ?
C009 H009 1.0000 . ?
C00B C00D 1.393(2) . ?
C00B H00B 0.9500 . ?
C00C C00E 1.390(3) . ?
C00C H00C 0.9500 . ?
C00D C00E 1.387(3) . ?
C00D H00D 0.9500 . ?
C00E H00E 0.9500 . ?
C00F C00J 1.510(2) . ?
C00F H00A 0.9900 . ?
C00F H00F 0.9900 . ?
C00G C00J 1.379(2) . ?
C00G C00I 1.391(2) . ?
C00G H00G 0.9500 . ?
C00H H00H 0.9900 . ?
C00H H00I 0.9900 . ?
C00I C00L 1.383(3) . ?
C00I H00I 0.9500 . ?
C00J C00M 1.396(2) . ?
C00K C00M 1.380(2) . ?
C00K C00L 1.390(3) . ?
C00K H00K 0.9500 . ?
C00M H00M 0.9500 . ?
C00N H00J 0.9800 . ?
C00N H00L 0.9800 . ?
C00N H00N 0.9800 . ?
C00O H00O 0.9800 . ?
C00O H00P 0.9800 . ?
C00O H00Q 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
C00N O001 C009 114.16(13) . . ?
C00L O004 C00O 116.88(15) . . ?
C008 N005 C00A 112.01(13) . . ?
C008 N005 C00H 123.09(13) . . ?
C00A N005 C00H 124.91(13) . . ?
C00B C006 C007 121.54(15) . . ?
C00B C006 C00A 130.15(14) . . ?
C007 C006 C00A 108.28(14) . . ?
C00C C007 C006 121.53(15) . . ?
C00C C007 C008 130.28(15) . . ?
C006 C007 C008 108.12(13) . . ?
O003 C008 N005 124.69(15) . . ?
O003 C008 C007 129.36(15) . . ?
N005 C008 C007 105.96(13) . . ?
O001 C009 C00H 106.38(13) . . ?
O001 C009 C00F 112.29(13) . . ?
C00H C009 C00F 111.26(14) . . ?
O001 C009 H009 108.9 . . ?
C00H C009 H009 108.9 . . ?
C00F C009 H009 108.9 . . ?
O002 C00A N005 125.44(15) . . ?
O002 C00A C006 128.98(15) . . ?
N005 C00A C006 105.57(13) . . ?
C006 C00B C00D 117.18(16) . . ?
C006 C00B H00B 121.4 . . ?
C00D C00B H00B 121.4 . . ?
C007 C00C C00E 117.23(16) . . ?
C007 C00C H00C 121.4 . . ?
C00E C00C H00C 121.4 . . ?
C00E C00D C00B 121.35(16) . . ?
C00E C00D H00D 119.3 . . ?
C00B C00D H00D 119.3 . . ?
C00D C00E C00C 121.15(16) . . ?
C00D C00E H00E 119.4 . . ?
C00C C00E H00E 119.4 . . ?
C00J C00F C009 112.79(13) . . ?
C00J C00F H00A 109.0 . . ?
C009 C00F H00A 109.0 . . ?
C00J C00F H00F 109.0 . . ?
C009 C00F H00F 109.0 . . ?
H00A C00F H00F 107.8 . . ?
C00J C00G C00I 122.23(17) . . ?
C00J C00G H00G 118.9 . . ?
C00I C00G H00G 118.9 . . ?
N005 C00H C009 112.09(13) . . ?
N005 C00H H00H 109.2 . . ?
C009 C00H H00H 109.2 . . ?
N005 C00H H00I 109.2 . . ?
C009 C00H H00I 109.2 . . ?
H00H C00H H00I 107.9 . . ?
C00L C00I C00G 119.37(16) . . ?
C00L C00I H00I 120.3 . . ?
C00G C00I H00I 120.3 . . ?
C00G C00J C00M 117.23(16) . . ?
C00G C00J C00F 121.92(16) . . ?
C00M C00J C00F 120.85(16) . . ?
C00M C00K C00L 119.92(16) . . ?
C00M C00K H00K 120.0 . . ?
C00L C00K H00K 120.0 . . ?
O004 C00L C00I 124.44(16) . . ?
O004 C00L C00K 115.95(16) . . ?
C00I C00L C00K 119.60(16) . . ?
C00K C00M C00J 121.63(16) . . ?
C00K C00M H00M 119.2 . . ?
C00J C00M H00M 119.2 . . ?
O001 C00N H00J 109.5 . . ?
O001 C00N H00L 109.5 . . ?
H00J C00N H00L 109.5 . . ?
O001 C00N H00N 109.5 . . ?
H00J C00N H00N 109.5 . . ?
H00L C00N H00N 109.5 . . ?
O004 C00O H00O 109.5 . . ?
O004 C00O H00P 109.5 . . ?
H00O C00O H00P 109.5 . . ?
O004 C00O H00Q 109.5 . . ?
H00O C00O H00Q 109.5 . . ?
H00P C00O H00Q 109.5 . . ?

_refine_diff_density_max         0.438
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.062



