# Electronic Supplementary Material (ESI) for Green 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_123_a
_database_code_depnum_ccdc_archive 'CCDC 1876586'
loop_
_audit_author_name
_audit_author_address
'pushap raj'
;chemsitry, IIT ROPAR
India
;
_audit_update_record             
;
2018-11-01 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;
_audit_creation_date             2018-11-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_systematic        
2-amino-4-(3-nitrophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
_chemical_formula_moiety         'C16 H13 N3 O4'
_chemical_formula_sum            'C16 H13 N3 O4'
_chemical_formula_weight         311.30
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   9.0134(4)
_cell_length_b                   9.0528(4)
_cell_length_c                   9.6602(5)
_cell_angle_alpha                70.923(2)
_cell_angle_beta                 76.940(2)
_cell_angle_gamma                75.474(2)
_cell_volume                     712.15(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7545
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.47
_cell_measurement_theta_min      2.32
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker, 2016/2) was used for absorption correction.'
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.4516
_exptl_crystal_description       needle
_exptl_crystal_F_000             324.1788
_exptl_crystal_preparation       'slow evaporation'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17207
_diffrn_reflns_theta_full        28.2789
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.26
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9963
_diffrn_measured_fraction_theta_max 0.9963
_diffrn_measurement_device_type  'APEXII Kappa CCD (Bruker)'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              -11
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2855
_reflns_number_total             3514
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.2603
_refine_diff_density_min         -0.3180
_refine_diff_density_rms         0.0453
_refine_ls_d_res_high            0.7501
_refine_ls_d_res_low             9.0159
_refine_ls_goodness_of_fit_ref   1.0960
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    19
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3514
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.0960
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0488P)²+0.2263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1239
_refine_special_details          'olex 2'
_olex2_refinement_description    
;
;
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_refinement_flags_posn
O1 O 0.93371(12) -0.02780(11) 0.21200(13) 0.0380(3) Uani 1.000000 .
O2 O 0.23908(18) 0.68815(17) 0.24265(18) 0.0758(5) Uani 1.000000 .
O3 O 0.87330(13) 0.51828(12) 0.16304(14) 0.0453(3) Uani 1.000000 .
N1 N 0.79582(18) -0.13793(16) 0.12315(17) 0.0411(3) Uani 1.000000 .
N2 N 0.46385(17) 0.17735(18) 0.0071(2) 0.0558(4) Uani 1.000000 .
C1 C 1.15751(18) 0.18524(19) 0.3308(2) 0.0431(4) Uani 1.000000 .
H1c H 1.09641(18) 0.18035(19) 0.4282(2) 0.0517(4) Uiso 1.000000 R
H1d H 1.26612(18) 0.16631(19) 0.3400(2) 0.0517(4) Uiso 1.000000 R
C2 C 1.13018(17) 0.05727(17) 0.27486(18) 0.0374(3) Uani 1.000000 .
H2a H 1.21099(17) 0.04178(17) 0.19266(18) 0.0449(4) Uiso 1.000000 R
H2b H 1.13559(17) -0.04253(17) 0.35341(18) 0.0449(4) Uiso 1.000000 R
C3 C 0.97599(16) 0.10231(16) 0.22543(15) 0.0308(3) Uani 1.000000 .
C4 C 0.88647(15) 0.24758(15) 0.19741(15) 0.0293(3) Uani 1.000000 .
C5 C 0.72517(15) 0.27881(15) 0.16202(15) 0.0288(3) Uani 1.000000 .
H5 H 0.71300(15) 0.37369(15) 0.07666(15) 0.0346(3) Uiso 1.000000 R
C6 C 0.60170(15) 0.30800(16) 0.29217(15) 0.0304(3) Uani 1.000000 .
C7 C 0.48486(16) 0.44237(16) 0.27254(16) 0.0332(3) Uani 1.000000 .
H7 H 0.48242(16) 0.51827(16) 0.18051(16) 0.0399(4) Uiso 1.000000 R
C8 C 0.37201(16) 0.46159(17) 0.39216(18) 0.0368(3) Uani 1.000000 .
N9 N 0.24700(16) 0.60270(17) 0.36814(18) 0.0487(4) Uani 1.000000 .
O10 O 0.15389(18) 0.6274(2) 0.47419(18) 0.0844(5) Uani 1.000000 .
C11 C 0.70613(15) 0.13803(16) 0.12033(15) 0.0305(3) Uani 1.000000 .
C12 C 0.80551(16) -0.00429(16) 0.14854(15) 0.0307(3) Uani 1.000000 .
C13 C 0.57372(17) 0.15644(17) 0.05685(17) 0.0361(3) Uani 1.000000 .
C14 C 0.37095(19) 0.3551(2) 0.53101(19) 0.0459(4) Uani 1.000000 .
H14 H 0.29437(19) 0.3724(2) 0.60969(19) 0.0551(5) Uiso 1.000000 R
C15 C 0.4878(2) 0.2212(2) 0.54992(19) 0.0505(4) Uani 1.000000 .
H15 H 0.4904(2) 0.1465(2) 0.64261(19) 0.0605(5) Uiso 1.000000 R
C16 C 0.60051(18) 0.19790(19) 0.43170(18) 0.0417(4) Uani 1.000000 .
H16 H 0.67737(18) 0.10647(19) 0.44577(18) 0.0501(4) Uiso 1.000000 R
C17 C 0.94933(16) 0.38316(16) 0.19489(16) 0.0341(3) Uani 1.000000 .
C18 C 1.11262(19) 0.34963(19) 0.2249(2) 0.0490(4) Uani 1.000000 .
H18a H 1.12383(19) 0.42950(19) 0.2666(2) 0.0588(5) Uiso 1.000000 R
H18b H 1.18338(19) 0.35837(19) 0.1318(2) 0.0588(5) Uiso 1.000000 R
H1a H 0.868(2) -0.222(3) 0.146(2) 0.056(6) Uiso 1.000000 .
H1b H 0.715(2) -0.143(2) 0.087(2) 0.058(6) Uiso 1.000000 .


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
O1 C3 1.3772(16) . ?
O1 C12 1.3667(16) . ?
O2 N9 1.213(2) . ?
O3 C17 1.2203(17) . ?
N1 C12 1.3372(18) . ?
N1 H1a 0.87(2) . ?
N1 H1b 0.89(2) . ?
N2 C13 1.1440(19) . ?
C1 H1c 0.9700 . ?
C1 H1d 0.9700 . ?
C1 C2 1.519(2) . ?
C1 C18 1.522(2) . ?
C2 H2a 0.9700 . ?
C2 H2b 0.9700 . ?
C2 C3 1.4880(19) . ?
C3 C4 1.3370(18) . ?
C4 C5 1.5052(18) . ?
C4 C17 1.4666(18) . ?
C5 H5 0.9800 . ?
C5 C6 1.5252(19) . ?
C5 C11 1.5141(18) . ?
C6 C7 1.3862(18) . ?
C6 C16 1.390(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.383(2) . ?
C8 N9 1.4689(19) . ?
C8 C14 1.372(2) . ?
N9 O10 1.2129(19) . ?
C11 C12 1.3559(18) . ?
C11 C13 1.4116(19) . ?
C14 H14 0.9300 . ?
C14 C15 1.384(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.381(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.501(2) . ?
C18 H18a 0.9700 . ?
C18 H18b 0.9700 . ?

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
C12 O1 C3 118.70(10) . . ?
H1a N1 C12 118.9(13) . . ?
H1b N1 C12 121.0(13) . . ?
H1b N1 H1a 120.1(18) . . ?
H1d C1 H1c 108.1 . . ?
C2 C1 H1c 109.52(9) . . ?
C2 C1 H1d 109.52(8) . . ?
C18 C1 H1c 109.52(10) . . ?
C18 C1 H1d 109.52(8) . . ?
C18 C1 C2 110.62(13) . . ?
H2a C2 C1 109.43(9) . . ?
H2b C2 C1 109.43(9) . . ?
H2b C2 H2a 108.0 . . ?
C3 C2 C1 111.05(12) . . ?
C3 C2 H2a 109.43(8) . . ?
C3 C2 H2b 109.43(8) . . ?
C2 C3 O1 110.90(11) . . ?
C4 C3 O1 122.83(12) . . ?
C4 C3 C2 126.26(12) . . ?
C5 C4 C3 122.45(12) . . ?
C17 C4 C3 119.07(12) . . ?
C17 C4 C5 118.43(11) . . ?
H5 C5 C4 108.60(7) . . ?
C6 C5 C4 111.66(11) . . ?
C6 C5 H5 108.60(7) . . ?
C11 C5 C4 108.69(10) . . ?
C11 C5 H5 108.60(7) . . ?
C11 C5 C6 110.63(11) . . ?
C7 C6 C5 120.64(12) . . ?
C16 C6 C5 120.81(12) . . ?
C16 C6 C7 118.51(13) . . ?
H7 C7 C6 120.58(8) . . ?
C8 C7 C6 118.84(14) . . ?
C8 C7 H7 120.58(9) . . ?
N9 C8 C7 118.00(14) . . ?
C14 C8 C7 123.22(14) . . ?
C14 C8 N9 118.78(14) . . ?
C8 N9 O2 118.72(14) . . ?
O10 N9 O2 122.56(16) . . ?
O10 N9 C8 118.71(16) . . ?
C12 C11 C5 122.78(12) . . ?
C13 C11 C5 117.28(11) . . ?
C13 C11 C12 119.84(12) . . ?
N1 C12 O1 110.54(12) . . ?
C11 C12 O1 121.68(12) . . ?
C11 C12 N1 127.77(13) . . ?
C11 C13 N2 177.02(16) . . ?
H14 C14 C8 121.16(9) . . ?
C15 C14 C8 117.67(15) . . ?
C15 C14 H14 121.16(10) . . ?
H15 C15 C14 119.88(10) . . ?
C16 C15 C14 120.25(15) . . ?
C16 C15 H15 119.88(10) . . ?
C15 C16 C6 121.49(15) . . ?
H16 C16 C6 119.25(9) . . ?
H16 C16 C15 119.25(10) . . ?
C4 C17 O3 120.73(13) . . ?
C18 C17 O3 121.83(13) . . ?
C18 C17 C4 117.36(12) . . ?
C17 C18 C1 112.87(13) . . ?
H18a C18 C1 109.01(9) . . ?
H18a C18 C17 109.01(8) . . ?
H18b C18 C1 109.01(10) . . ?
H18b C18 C17 109.01(10) . . ?
H18b C18 H18a 107.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
