# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_No1
_database_code_depnum_ccdc_archive 'CCDC 1878962'
loop_
_audit_author_name
_audit_author_address
'Ha Jin Lee'
;Yeungnam University
South Korea
;
_audit_update_record             
;
2018-11-14 deposited with the CCDC.	2019-05-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
3-Isopropyl-12-methyl-6H-isochromeno[4,3-c]quinoline-6,11(12H)-dione
_chemical_name_common            ?
_chemical_melting_point          501
_chemical_formula_moiety         'C20 H17 N O3'
_chemical_formula_sum            'C20 H17 N O3'
_chemical_formula_weight         319.35

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.9877(7)
_cell_length_b                   16.1253(9)
_cell_length_c                   7.4653(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.6634(19)
_cell_angle_gamma                90
_cell_volume                     1525.43(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    8854
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      27.93

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7178
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49338
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0940
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.526
_diffrn_reflns_theta_max         28.364
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3798
_reflns_number_gt                2448
_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    'Bruker SHELXTL'
_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)+(0.0492P)²+0.9852P] 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         3798
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1386
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
O1 O -0.06965(9) 0.66607(7) 0.02172(16) 0.0261(3) Uani 1 1 d . . . . .
C1 C -0.15539(14) 0.70913(11) -0.0737(2) 0.0270(4) Uani 1 1 d . . . . .
C2 C -0.25907(14) 0.67573(11) -0.0712(2) 0.0273(4) Uani 1 1 d . . . . .
C3 C -0.34656(16) 0.72244(13) -0.1565(3) 0.0363(5) Uani 1 1 d . . . . .
H3 H -0.3372 0.7719 -0.2177 0.044 Uiso 1 1 calc R U . . .
C4 C -0.44630(17) 0.69606(14) -0.1508(3) 0.0424(5) Uani 1 1 d . . . . .
H4 H -0.5056 0.7266 -0.2103 0.051 Uiso 1 1 calc R U . . .
C5 C -0.45876(16) 0.62426(14) -0.0572(3) 0.0434(5) Uani 1 1 d . . . . .
H5 H -0.5270 0.6075 -0.0495 0.052 Uiso 1 1 calc R U . . .
C6 C -0.37325(15) 0.57661(13) 0.0255(3) 0.0372(5) Uani 1 1 d . . . . .
H6 H -0.3840 0.5276 0.0871 0.045 Uiso 1 1 calc R U . . .
C7 C -0.27035(14) 0.60065(11) 0.0182(2) 0.0265(4) Uani 1 1 d . . . . .
C8 C -0.17466(14) 0.55542(11) 0.1002(2) 0.0245(4) Uani 1 1 d . . . . .
C9 C -0.17557(15) 0.47084(11) 0.1726(2) 0.0274(4) Uani 1 1 d . . . . .
N1 N -0.07876(12) 0.43640(9) 0.2539(2) 0.0265(3) Uani 1 1 d . . . . .
C10 C 0.01673(14) 0.47854(11) 0.2758(2) 0.0249(4) Uani 1 1 d . . . . .
C11 C 0.11154(15) 0.44514(12) 0.3737(3) 0.0325(4) Uani 1 1 d . . . . .
H11 H 0.1122 0.3925 0.4281 0.039 Uiso 1 1 calc R U . . .
C12 C 0.20411(16) 0.48903(13) 0.3909(3) 0.0352(5) Uani 1 1 d . . . . .
H12 H 0.2669 0.4656 0.4588 0.042 Uiso 1 1 calc R U . . .
C13 C 0.20839(15) 0.56727(13) 0.3110(3) 0.0332(4) Uani 1 1 d . . . . .
C14 C 0.11476(14) 0.59949(12) 0.2138(3) 0.0293(4) Uani 1 1 d . . . . .
H14 H 0.1151 0.6516 0.1574 0.035 Uiso 1 1 calc R U . . .
C15 C 0.01881(14) 0.55710(11) 0.1961(2) 0.0242(4) Uani 1 1 d . . . . .
C16 C -0.07976(13) 0.59166(11) 0.1040(2) 0.0229(4) Uani 1 1 d . . . . .
O2 O -0.13664(11) 0.77128(9) -0.1499(2) 0.0394(4) Uani 1 1 d . . . . .
O3 O -0.25713(10) 0.43031(9) 0.1600(2) 0.0388(4) Uani 1 1 d . . . . .
C17 C -0.07836(17) 0.35064(12) 0.3191(3) 0.0359(5) Uani 1 1 d . . . . .
H17A H -0.0326 0.3173 0.2613 0.054 Uiso 1 1 calc R U . . .
H17B H -0.1495 0.3285 0.2879 0.054 Uiso 1 1 calc R U . . .
H17C H -0.0527 0.3494 0.4513 0.054 Uiso 1 1 calc R U . . .
C18 C 0.30862(16) 0.61923(15) 0.3301(3) 0.0445(5) Uani 1 1 d . . . . .
H18 H 0.3076 0.6426 0.2071 0.053 Uiso 1 1 calc R U . . .
C19 C 0.40855(18) 0.57087(18) 0.3842(4) 0.0653(8) Uani 1 1 d . . . . .
H19A H 0.4682 0.6069 0.3828 0.098 Uiso 1 1 calc R U . . .
H19B H 0.4079 0.5257 0.2982 0.098 Uiso 1 1 calc R U . . .
H19C H 0.4145 0.5486 0.5067 0.098 Uiso 1 1 calc R U . . .
C20 C 0.30552(17) 0.69205(14) 0.4559(3) 0.0454(6) Uani 1 1 d . . . . .
H20A H 0.3068 0.6720 0.5789 0.068 Uiso 1 1 calc R U . . .
H20B H 0.2414 0.7236 0.4115 0.068 Uiso 1 1 calc R U . . .
H20C H 0.3663 0.7273 0.4582 0.068 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
O1 C16 1.367(2) . ?
O1 C1 1.372(2) . ?
C1 O2 1.203(2) . ?
C1 C2 1.454(3) . ?
C2 C3 1.395(3) . ?
C2 C7 1.405(3) . ?
C3 C4 1.373(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9400 . ?
C6 C7 1.404(3) . ?
C6 H6 0.9400 . ?
C7 C8 1.455(2) . ?
C8 C16 1.359(2) . ?
C8 C9 1.468(2) . ?
C9 O3 1.231(2) . ?
C9 N1 1.387(2) . ?
N1 C10 1.392(2) . ?
N1 C17 1.466(2) . ?
C10 C11 1.395(3) . ?
C10 C15 1.402(2) . ?
C11 C12 1.377(3) . ?
C11 H11 0.9400 . ?
C12 C13 1.402(3) . ?
C12 H12 0.9400 . ?
C13 C14 1.374(3) . ?
C13 C18 1.528(3) . ?
C14 C15 1.402(2) . ?
C14 H14 0.9400 . ?
C15 C16 1.427(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C18 C19 1.492(3) . ?
C18 C20 1.510(3) . ?
C18 H18 0.9900 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 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
C16 O1 C1 122.04(14) . . ?
O2 C1 O1 116.21(17) . . ?
O2 C1 C2 126.77(18) . . ?
O1 C1 C2 117.02(16) . . ?
C3 C2 C7 121.50(18) . . ?
C3 C2 C1 117.25(17) . . ?
C7 C2 C1 121.23(17) . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 120.6(2) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C2 117.09(17) . . ?
C6 C7 C8 125.28(18) . . ?
C2 C7 C8 117.60(16) . . ?
C16 C8 C7 118.70(16) . . ?
C16 C8 C9 118.19(16) . . ?
C7 C8 C9 123.06(16) . . ?
O3 C9 N1 120.23(17) . . ?
O3 C9 C8 122.79(17) . . ?
N1 C9 C8 116.97(15) . . ?
C9 N1 C10 123.69(15) . . ?
C9 N1 C17 117.39(16) . . ?
C10 N1 C17 118.91(16) . . ?
N1 C10 C11 122.30(17) . . ?
N1 C10 C15 119.40(16) . . ?
C11 C10 C15 118.30(17) . . ?
C12 C11 C10 120.20(18) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 122.57(18) . . ?
C11 C12 H12 118.7 . . ?
C13 C12 H12 118.7 . . ?
C14 C13 C12 116.87(18) . . ?
C14 C13 C18 118.61(19) . . ?
C12 C13 C18 124.50(18) . . ?
C13 C14 C15 122.06(18) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
C14 C15 C10 119.99(17) . . ?
C14 C15 C16 122.68(17) . . ?
C10 C15 C16 117.30(16) . . ?
C8 C16 O1 122.97(16) . . ?
C8 C16 C15 123.77(16) . . ?
O1 C16 C15 113.26(15) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C20 112.23(19) . . ?
C19 C18 C13 114.3(2) . . ?
C20 C18 C13 110.23(17) . . ?
C19 C18 H18 106.5 . . ?
C20 C18 H18 106.5 . . ?
C13 C18 H18 106.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 O1 C1 O2 -175.52(16) . . . . ?
C16 O1 C1 C2 5.0(2) . . . . ?
O2 C1 C2 C3 -4.0(3) . . . . ?
O1 C1 C2 C3 175.39(16) . . . . ?
O2 C1 C2 C7 177.76(18) . . . . ?
O1 C1 C2 C7 -2.9(2) . . . . ?
C7 C2 C3 C4 1.4(3) . . . . ?
C1 C2 C3 C4 -176.87(18) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C3 C4 C5 C6 -2.4(3) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C5 C6 C7 C2 1.9(3) . . . . ?
C5 C6 C7 C8 179.94(18) . . . . ?
C3 C2 C7 C6 -3.0(3) . . . . ?
C1 C2 C7 C6 175.23(17) . . . . ?
C3 C2 C7 C8 178.84(17) . . . . ?
C1 C2 C7 C8 -3.0(2) . . . . ?
C6 C7 C8 C16 -171.11(18) . . . . ?
C2 C7 C8 C16 6.9(2) . . . . ?
C6 C7 C8 C9 11.5(3) . . . . ?
C2 C7 C8 C9 -170.47(16) . . . . ?
C16 C8 C9 O3 -173.29(17) . . . . ?
C7 C8 C9 O3 4.1(3) . . . . ?
C16 C8 C9 N1 5.2(2) . . . . ?
C7 C8 C9 N1 -177.41(15) . . . . ?
O3 C9 N1 C10 -179.02(16) . . . . ?
C8 C9 N1 C10 2.5(2) . . . . ?
O3 C9 N1 C17 1.2(3) . . . . ?
C8 C9 N1 C17 -177.28(16) . . . . ?
C9 N1 C10 C11 173.69(16) . . . . ?
C17 N1 C10 C11 -6.6(2) . . . . ?
C9 N1 C10 C15 -6.8(2) . . . . ?
C17 N1 C10 C15 172.98(16) . . . . ?
N1 C10 C11 C12 179.70(16) . . . . ?
C15 C10 C11 C12 0.2(3) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C11 C12 C13 C18 178.46(19) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C18 C13 C14 C15 -177.48(17) . . . . ?
C13 C14 C15 C10 -1.4(3) . . . . ?
C13 C14 C15 C16 176.57(17) . . . . ?
N1 C10 C15 C14 -178.66(16) . . . . ?
C11 C10 C15 C14 0.9(2) . . . . ?
N1 C10 C15 C16 3.3(2) . . . . ?
C11 C10 C15 C16 -177.16(16) . . . . ?
C7 C8 C16 O1 -5.2(3) . . . . ?
C9 C8 C16 O1 172.37(15) . . . . ?
C7 C8 C16 C15 173.66(16) . . . . ?
C9 C8 C16 C15 -8.8(3) . . . . ?
C1 O1 C16 C8 -1.0(2) . . . . ?
C1 O1 C16 C15 -179.98(15) . . . . ?
C14 C15 C16 C8 -173.41(17) . . . . ?
C10 C15 C16 C8 4.6(3) . . . . ?
C14 C15 C16 O1 5.5(2) . . . . ?
C10 C15 C16 O1 -176.48(14) . . . . ?
C14 C13 C18 C19 -161.8(2) . . . . ?
C12 C13 C18 C19 20.1(3) . . . . ?
C14 C13 C18 C20 70.7(3) . . . . ?
C12 C13 C18 C20 -107.4(2) . . . . ?

_refine_diff_density_max         0.429
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/EtOAc'
