# 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_20200612_0m
_database_code_depnum_ccdc_archive 'CCDC 2013547'
loop_
_audit_author_name
_audit_author_address
'Jung Su Park'
;Sookmyung Women University
South Korea
;
_audit_update_record             
;
2020-07-02 deposited with the CCDC.	2020-09-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
ethyl 12-hydroxy-4-methyl-10-oxo-10,12-dihydroisoindolo[1,2-b]quinazoline-12-carboxylate
;
_chemical_name_common            isoindoloquinazolinone
_chemical_melting_point          ?
_chemical_formula_moiety         "'C19 H16 N2 O4"
_chemical_formula_sum            'C19 H16 N2 O4'
_chemical_formula_weight         336.34

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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   7.67620(10)
_cell_length_b                   12.3159(2)
_cell_length_c                   17.1409(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1620.49(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6566
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      21.08

_exptl_crystal_description       Block
_exptl_crystal_colour            Silver
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2082
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.036
_diffrn_reflns_theta_max         28.326
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.515
_diffrn_reflns_point_group_measured_fraction_full 0.518
_reflns_number_total             2082
_reflns_number_gt                1605
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_reflns_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1230P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   1.4(18)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2082
_refine_ls_number_parameters     226
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1613
_refine_ls_wR_factor_gt          0.1498
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.023
_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 0.2469(4) 0.3983(2) 0.47142(17) 0.0661(7) Uani 1 1 d . . . . .
O2 O 0.2756(3) 0.41078(18) 0.29541(14) 0.0538(6) Uani 1 1 d . . . . .
H2A H 0.3568 0.4510 0.2840 0.081 Uiso 1 1 calc R U . . .
O3 O -0.0288(4) 0.30729(19) 0.3243(2) 0.0727(7) Uani 1 1 d . . . . .
O4 O -0.1312(3) 0.4518(2) 0.38892(18) 0.0707(8) Uani 1 1 d . . . . .
N1 N 0.1895(3) 0.54032(18) 0.39247(14) 0.0430(5) Uani 1 1 d . . . . .
N2 N 0.2038(4) 0.7257(2) 0.42958(17) 0.0491(6) Uani 1 1 d . . . . .
C1 C 0.2418(4) 0.4974(3) 0.46279(19) 0.0487(7) Uani 1 1 d . . . . .
C2 C 0.1378(4) 0.4724(2) 0.32456(17) 0.0445(6) Uani 1 1 d . . . . .
C3 C 0.0830(4) 0.5600(3) 0.26757(17) 0.0457(6) Uani 1 1 d . . . . .
C4 C 0.0226(5) 0.5451(3) 0.19207(19) 0.0564(8) Uani 1 1 d . . . . .
H4A H 0.0129 0.4762 0.1702 0.068 Uiso 1 1 calc R U . . .
C5 C -0.0231(5) 0.6385(3) 0.1502(2) 0.0650(9) Uani 1 1 d . . . . .
H5A H -0.0659 0.6321 0.0997 0.078 Uiso 1 1 calc R U . . .
C6 C -0.0049(5) 0.7406(3) 0.1836(2) 0.0603(9) Uani 1 1 d . . . . .
H6A H -0.0370 0.8009 0.1543 0.072 Uiso 1 1 calc R U . . .
C7 C 0.0586(4) 0.7571(3) 0.2583(2) 0.0508(8) Uani 1 1 d . . . . .
C8 C 0.1013(4) 0.6626(2) 0.29987(18) 0.0445(6) Uani 1 1 d . . . . .
C9 C 0.1697(4) 0.6513(2) 0.37954(18) 0.0436(6) Uani 1 1 d . . . . .
C10 C 0.2666(4) 0.6897(3) 0.5018(2) 0.0510(8) Uani 1 1 d . . . . .
C11 C 0.3071(6) 0.7676(3) 0.5585(2) 0.0687(10) Uani 1 1 d . . . . .
H11A H 0.2934 0.8410 0.5473 0.082 Uiso 1 1 calc R U . . .
C12 C 0.3675(6) 0.7357(4) 0.6312(3) 0.0786(13) Uani 1 1 d . . . . .
H12A H 0.3925 0.7877 0.6689 0.094 Uiso 1 1 calc R U . . .
C13 C 0.3908(6) 0.6261(4) 0.6480(2) 0.0733(11) Uani 1 1 d . . . . .
H13A H 0.4340 0.6053 0.6965 0.088 Uiso 1 1 calc R U . . .
C14 C 0.3507(5) 0.5491(3) 0.5939(2) 0.0642(9) Uani 1 1 d . . . . .
H14A H 0.3652 0.4759 0.6058 0.077 Uiso 1 1 calc R U . . .
C15 C 0.2877(4) 0.5797(3) 0.52018(19) 0.0500(7) Uani 1 1 d . . . . .
C16 C -0.0164(5) 0.3990(2) 0.34664(17) 0.0501(7) Uani 1 1 d . . . . .
C17 C -0.2920(7) 0.3955(5) 0.4101(3) 0.0959(17) Uani 1 1 d D . . . .
H17A H -0.3916 0.4378 0.3930 0.115 Uiso 1 1 calc R U . . .
H17B H -0.2963 0.3256 0.3841 0.115 Uiso 1 1 calc R U . . .
C18 C -0.3003(11) 0.3798(8) 0.4940(4) 0.136(3) Uani 1 1 d D . . . .
H18A H -0.4059 0.3423 0.5071 0.204 Uiso 1 1 calc R U . . .
H18B H -0.2985 0.4492 0.5195 0.204 Uiso 1 1 calc R U . . .
H18C H -0.2020 0.3377 0.5107 0.204 Uiso 1 1 calc R U . . .
C19 C 0.0827(6) 0.8680(3) 0.2909(3) 0.0636(9) Uani 1 1 d . . . . .
H19A H 0.0448 0.9208 0.2534 0.095 Uiso 1 1 calc R U . . .
H19B H 0.2036 0.8794 0.3026 0.095 Uiso 1 1 calc R U . . .
H19C H 0.0151 0.8753 0.3377 0.095 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 C1 1.230(4) . ?
O2 C2 1.395(4) . ?
O2 H2A 0.8200 . ?
O3 C16 1.196(4) . ?
O4 C16 1.314(4) . ?
O4 C17 1.462(5) . ?
N1 C1 1.376(4) . ?
N1 C9 1.393(4) . ?
N1 C2 1.487(4) . ?
N2 C9 1.282(4) . ?
N2 C10 1.400(5) . ?
C1 C15 1.456(5) . ?
C2 C3 1.515(4) . ?
C2 C16 1.537(4) . ?
C3 C8 1.386(5) . ?
C3 C4 1.387(4) . ?
C4 C5 1.400(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.388(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.385(5) . ?
C6 H6A 0.9300 . ?
C7 C8 1.404(4) . ?
C7 C19 1.487(5) . ?
C8 C9 1.470(5) . ?
C10 C15 1.400(5) . ?
C10 C11 1.400(5) . ?
C11 C12 1.388(6) . ?
C11 H11A 0.9300 . ?
C12 C13 1.392(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.362(6) . ?
C13 H13A 0.9300 . ?
C14 C15 1.405(5) . ?
C14 H14A 0.9300 . ?
C17 C18 1.451(7) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C2 O2 H2A 109.5 . . ?
C16 O4 C17 117.9(3) . . ?
C1 N1 C9 123.3(3) . . ?
C1 N1 C2 123.2(2) . . ?
C9 N1 C2 113.5(2) . . ?
C9 N2 C10 115.8(3) . . ?
O1 C1 N1 119.7(3) . . ?
O1 C1 C15 127.0(3) . . ?
N1 C1 C15 113.3(3) . . ?
O2 C2 N1 112.6(2) . . ?
O2 C2 C3 111.5(2) . . ?
N1 C2 C3 100.3(2) . . ?
O2 C2 C16 110.6(2) . . ?
N1 C2 C16 110.1(2) . . ?
C3 C2 C16 111.3(2) . . ?
C8 C3 C4 121.8(3) . . ?
C8 C3 C2 111.3(3) . . ?
C4 C3 C2 126.9(3) . . ?
C3 C4 C5 116.9(3) . . ?
C3 C4 H4A 121.5 . . ?
C5 C4 H4A 121.5 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5A 119.7 . . ?
C4 C5 H5A 119.7 . . ?
C7 C6 C5 123.3(3) . . ?
C7 C6 H6A 118.3 . . ?
C5 C6 H6A 118.3 . . ?
C6 C7 C8 115.5(3) . . ?
C6 C7 C19 121.8(3) . . ?
C8 C7 C19 122.8(3) . . ?
C3 C8 C7 121.9(3) . . ?
C3 C8 C9 108.7(2) . . ?
C7 C8 C9 129.3(3) . . ?
N2 C9 N1 124.9(3) . . ?
N2 C9 C8 128.8(3) . . ?
N1 C9 C8 106.2(2) . . ?
C15 C10 N2 123.1(3) . . ?
C15 C10 C11 118.8(3) . . ?
N2 C10 C11 118.2(3) . . ?
C12 C11 C10 120.2(4) . . ?
C12 C11 H11A 119.9 . . ?
C10 C11 H11A 119.9 . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12A 119.9 . . ?
C13 C12 H12A 119.9 . . ?
C14 C13 C12 120.3(4) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C13 C14 C15 120.3(4) . . ?
C13 C14 H14A 119.9 . . ?
C15 C14 H14A 119.9 . . ?
C10 C15 C14 120.1(3) . . ?
C10 C15 C1 119.6(3) . . ?
C14 C15 C1 120.3(3) . . ?
O3 C16 O4 126.2(3) . . ?
O3 C16 C2 122.6(3) . . ?
O4 C16 C2 111.1(3) . . ?
C18 C17 O4 110.3(5) . . ?
C18 C17 H17A 109.6 . . ?
O4 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
O4 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C7 C19 H19A 109.5 . . ?
C7 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C7 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C9 N1 C1 O1 175.9(3) . . . . ?
C2 N1 C1 O1 -0.1(5) . . . . ?
C9 N1 C1 C15 -4.7(4) . . . . ?
C2 N1 C1 C15 179.4(3) . . . . ?
C1 N1 C2 O2 -65.0(4) . . . . ?
C9 N1 C2 O2 118.7(3) . . . . ?
C1 N1 C2 C3 176.3(3) . . . . ?
C9 N1 C2 C3 0.1(3) . . . . ?
C1 N1 C2 C16 58.9(4) . . . . ?
C9 N1 C2 C16 -117.3(3) . . . . ?
O2 C2 C3 C8 -119.6(3) . . . . ?
N1 C2 C3 C8 -0.2(3) . . . . ?
C16 C2 C3 C8 116.3(3) . . . . ?
O2 C2 C3 C4 59.9(4) . . . . ?
N1 C2 C3 C4 179.3(3) . . . . ?
C16 C2 C3 C4 -64.2(4) . . . . ?
C8 C3 C4 C5 -1.5(5) . . . . ?
C2 C3 C4 C5 179.1(3) . . . . ?
C3 C4 C5 C6 1.0(6) . . . . ?
C4 C5 C6 C7 0.4(6) . . . . ?
C5 C6 C7 C8 -1.3(5) . . . . ?
C5 C6 C7 C19 177.6(4) . . . . ?
C4 C3 C8 C7 0.5(5) . . . . ?
C2 C3 C8 C7 -179.9(3) . . . . ?
C4 C3 C8 C9 -179.2(3) . . . . ?
C2 C3 C8 C9 0.3(3) . . . . ?
C6 C7 C8 C3 0.8(4) . . . . ?
C19 C7 C8 C3 -178.0(3) . . . . ?
C6 C7 C8 C9 -179.5(3) . . . . ?
C19 C7 C8 C9 1.7(5) . . . . ?
C10 N2 C9 N1 0.5(4) . . . . ?
C10 N2 C9 C8 179.4(3) . . . . ?
C1 N1 C9 N2 2.9(5) . . . . ?
C2 N1 C9 N2 179.2(3) . . . . ?
C1 N1 C9 C8 -176.2(3) . . . . ?
C2 N1 C9 C8 0.1(3) . . . . ?
C3 C8 C9 N2 -179.3(3) . . . . ?
C7 C8 C9 N2 1.0(5) . . . . ?
C3 C8 C9 N1 -0.2(3) . . . . ?
C7 C8 C9 N1 -180.0(3) . . . . ?
C9 N2 C10 C15 -1.6(5) . . . . ?
C9 N2 C10 C11 179.6(3) . . . . ?
C15 C10 C11 C12 0.3(6) . . . . ?
N2 C10 C11 C12 179.1(4) . . . . ?
C10 C11 C12 C13 1.0(7) . . . . ?
C11 C12 C13 C14 -1.5(7) . . . . ?
C12 C13 C14 C15 0.9(7) . . . . ?
N2 C10 C15 C14 -179.7(3) . . . . ?
C11 C10 C15 C14 -0.9(5) . . . . ?
N2 C10 C15 C1 -0.5(5) . . . . ?
C11 C10 C15 C1 178.3(3) . . . . ?
C13 C14 C15 C10 0.4(6) . . . . ?
C13 C14 C15 C1 -178.9(4) . . . . ?
O1 C1 C15 C10 -177.1(3) . . . . ?
N1 C1 C15 C10 3.5(4) . . . . ?
O1 C1 C15 C14 2.1(5) . . . . ?
N1 C1 C15 C14 -177.3(3) . . . . ?
C17 O4 C16 O3 -1.3(6) . . . . ?
C17 O4 C16 C2 175.8(4) . . . . ?
O2 C2 C16 O3 -16.2(4) . . . . ?
N1 C2 C16 O3 -141.3(3) . . . . ?
C3 C2 C16 O3 108.5(4) . . . . ?
O2 C2 C16 O4 166.6(3) . . . . ?
N1 C2 C16 O4 41.5(4) . . . . ?
C3 C2 C16 O4 -68.7(4) . . . . ?
C16 O4 C17 C18 114.8(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C17 H17B O3 0.97 2.63 3.421(6) 139.0 4_455

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.051

_shelxl_version_number           2013-4



