# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_t_a
_database_code_depnum_ccdc_archive 'CCDC 1956245'
loop_
_audit_author_name
_audit_author_address
isoquinolin
;shang hai jiao tong university
China
;
_audit_update_record             
;
2019-09-27 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
5,5-dimethyl-12-phenylindolo[2,1-a]isoquinolin-6(5H)-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H19 N O'
_chemical_formula_sum            'C24 H19 N O'
_chemical_formula_weight         337.40

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   10.3896(8)
_cell_length_b                   10.1601(12)
_cell_length_c                   17.175(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.570(8)
_cell_angle_gamma                90
_cell_volume                     1769.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    301(2)
_cell_measurement_reflns_used    8348
_cell_measurement_theta_min      5.28
_cell_measurement_theta_max      68.20

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.598
_shelx_estimated_absorpt_T_min   0.870
_shelx_estimated_absorpt_T_max   0.890
_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      301(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            13309
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.277
_diffrn_reflns_theta_max         68.288
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3197
_reflns_number_gt                2824
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0602P)²+0.3171P] 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         3197
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1152
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
N1 N 0.23107(12) 0.60205(12) 0.40435(7) 0.0511(3) Uani 1 1 d . . . . .
C1 C 0.12377(14) 0.54494(14) 0.35086(9) 0.0506(3) Uani 1 1 d . . . . .
O1 O 0.12977(15) 0.64685(15) 0.50474(8) 0.0865(4) Uani 1 1 d . . . . .
C3 C -0.08972(18) 0.46693(17) 0.29293(13) 0.0705(5) Uani 1 1 d . . . . .
H3 H -0.175949 0.448271 0.296344 0.085 Uiso 1 1 calc R U . . .
C2 C -0.00332(17) 0.51690(16) 0.35897(11) 0.0629(4) Uani 1 1 d . . . . .
H2 H -0.029221 0.531149 0.406811 0.075 Uiso 1 1 calc R U . . .
C4 C -0.05140(17) 0.44375(17) 0.22154(11) 0.0673(4) Uani 1 1 d . . . . .
H4 H -0.112607 0.411957 0.177817 0.081 Uiso 1 1 calc R U . . .
C5 C 0.07606(16) 0.46734(15) 0.21486(10) 0.0586(4) Uani 1 1 d . . . . .
H5 H 0.102060 0.449762 0.167407 0.070 Uiso 1 1 calc R U . . .
C6 C 0.16578(15) 0.51809(13) 0.28048(9) 0.0492(3) Uani 1 1 d . . . . .
C7 C 0.30306(14) 0.55436(13) 0.29242(8) 0.0479(3) Uani 1 1 d . . . . .
C9 C 0.46660(15) 0.65050(13) 0.41548(9) 0.0505(3) Uani 1 1 d . . . . .
C8 C 0.34066(14) 0.60545(13) 0.36780(8) 0.0476(3) Uani 1 1 d . . . . .
C10 C 0.47057(16) 0.70950(15) 0.48989(9) 0.0571(4) Uani 1 1 d . . . . .
C11 C 0.34471(18) 0.74088(15) 0.51771(9) 0.0579(4) Uani 1 1 d . . . . .
C12 C 0.22704(18) 0.65799(16) 0.47755(9) 0.0603(4) Uani 1 1 d . . . . .
C13 C 0.58425(16) 0.63286(16) 0.38993(10) 0.0597(4) Uani 1 1 d . . . . .
H13 H 0.582030 0.594151 0.340591 0.072 Uiso 1 1 calc R U . . .
C14 C 0.70323(18) 0.67165(19) 0.43636(12) 0.0735(5) Uani 1 1 d . . . . .
H14 H 0.780581 0.659476 0.418353 0.088 Uiso 1 1 calc R U . . .
C15 C 0.7074(2) 0.7284(2) 0.50944(13) 0.0876(6) Uani 1 1 d . . . . .
H15 H 0.787797 0.754069 0.541222 0.105 Uiso 1 1 calc R U . . .
C16 C 0.5929(2) 0.7474(2) 0.53560(11) 0.0793(5) Uani 1 1 d . . . . .
H16 H 0.597091 0.786549 0.585040 0.095 Uiso 1 1 calc R U . . .
C17 C 0.3052(2) 0.88451(17) 0.49455(11) 0.0687(5) Uani 1 1 d . . . . .
H17A H 0.289731 0.894011 0.437658 0.103 Uiso 1 1 calc R U . . .
H17B H 0.374985 0.942583 0.519392 0.103 Uiso 1 1 calc R U . . .
H17C H 0.226221 0.906212 0.512200 0.103 Uiso 1 1 calc R U . . .
C18 C 0.3607(2) 0.7265(2) 0.60845(10) 0.0803(6) Uani 1 1 d . . . . .
H18A H 0.276361 0.736480 0.622036 0.120 Uiso 1 1 calc R U . . .
H18B H 0.419882 0.792976 0.635116 0.120 Uiso 1 1 calc R U . . .
H18C H 0.395835 0.641032 0.624832 0.120 Uiso 1 1 calc R U . . .
C19 C 0.38438(14) 0.53061(14) 0.23261(8) 0.0473(3) Uani 1 1 d . . . . .
C20 C 0.41966(16) 0.40302(15) 0.21742(9) 0.0562(4) Uani 1 1 d . . . . .
H20 H 0.388976 0.332895 0.243093 0.067 Uiso 1 1 calc R U . . .
C21 C 0.49965(18) 0.37914(18) 0.16471(11) 0.0697(5) Uani 1 1 d . . . . .
H21 H 0.524287 0.293321 0.155987 0.084 Uiso 1 1 calc R U . . .
C22 C 0.54318(18) 0.48146(19) 0.12498(11) 0.0698(5) Uani 1 1 d . . . . .
H22 H 0.597632 0.465004 0.089676 0.084 Uiso 1 1 calc R U . . .
C23 C 0.50627(17) 0.60784(18) 0.13743(10) 0.0665(4) Uani 1 1 d . . . . .
H23 H 0.534518 0.677106 0.109925 0.080 Uiso 1 1 calc R U . . .
C24 C 0.42709(16) 0.63237(15) 0.19084(9) 0.0584(4) Uani 1 1 d . . . . .
H24 H 0.402130 0.718355 0.198864 0.070 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
N1 C12 1.3887(19) . ?
N1 C1 1.4063(19) . ?
N1 C8 1.4152(18) . ?
C1 C2 1.387(2) . ?
C1 C6 1.398(2) . ?
O1 C12 1.207(2) . ?
C3 C2 1.381(3) . ?
C3 C4 1.389(3) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C4 C5 1.375(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.444(2) . ?
C7 C8 1.3705(19) . ?
C7 C19 1.4849(19) . ?
C9 C13 1.397(2) . ?
C9 C10 1.404(2) . ?
C9 C8 1.458(2) . ?
C10 C16 1.395(3) . ?
C10 C11 1.520(2) . ?
C11 C12 1.521(2) . ?
C11 C18 1.538(2) . ?
C11 C17 1.545(2) . ?
C13 C14 1.375(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C24 1.385(2) . ?
C19 C20 1.387(2) . ?
C20 C21 1.377(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.373(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.370(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.382(2) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

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 N1 C1 125.77(13) . . ?
C12 N1 C8 125.26(13) . . ?
C1 N1 C8 108.68(11) . . ?
C2 C1 C6 121.98(15) . . ?
C2 C1 N1 130.98(14) . . ?
C6 C1 N1 107.03(12) . . ?
C2 C3 C4 121.83(16) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C3 C2 C1 117.13(16) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C5 C4 C3 120.69(17) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 118.88(16) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 119.40(14) . . ?
C5 C6 C7 132.41(14) . . ?
C1 C6 C7 108.18(13) . . ?
C8 C7 C6 107.49(12) . . ?
C8 C7 C19 128.83(13) . . ?
C6 C7 C19 123.61(13) . . ?
C13 C9 C10 119.09(15) . . ?
C13 C9 C8 121.53(13) . . ?
C10 C9 C8 119.36(14) . . ?
C7 C8 N1 108.56(13) . . ?
C7 C8 C9 133.31(13) . . ?
N1 C8 C9 117.96(12) . . ?
C16 C10 C9 118.22(16) . . ?
C16 C10 C11 120.39(15) . . ?
C9 C10 C11 121.24(14) . . ?
C10 C11 C12 113.75(12) . . ?
C10 C11 C18 112.83(15) . . ?
C12 C11 C18 107.81(14) . . ?
C10 C11 C17 108.41(13) . . ?
C12 C11 C17 105.30(14) . . ?
C18 C11 C17 108.35(14) . . ?
O1 C12 N1 120.30(16) . . ?
O1 C12 C11 122.30(14) . . ?
N1 C12 C11 117.24(13) . . ?
C14 C13 C9 121.25(16) . . ?
C14 C13 H13 119.4 . . ?
C9 C13 H13 119.4 . . ?
C15 C14 C13 119.73(18) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 120.04(18) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C10 121.67(17) . . ?
C15 C16 H16 119.2 . . ?
C10 C16 H16 119.2 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C24 C19 C20 118.20(13) . . ?
C24 C19 C7 122.11(13) . . ?
C20 C19 C7 119.70(13) . . ?
C21 C20 C19 120.68(15) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 120.30(16) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 119.89(16) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 120.00(16) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C19 120.88(15) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?

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
C12 N1 C1 C2 -7.7(3) . . . . ?
C8 N1 C1 C2 178.27(15) . . . . ?
C12 N1 C1 C6 171.73(13) . . . . ?
C8 N1 C1 C6 -2.29(15) . . . . ?
C4 C3 C2 C1 0.8(3) . . . . ?
C6 C1 C2 C3 -3.1(2) . . . . ?
N1 C1 C2 C3 176.24(15) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C3 C4 C5 C6 -1.6(3) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C4 C5 C6 C7 -179.20(15) . . . . ?
C2 C1 C6 C5 3.1(2) . . . . ?
N1 C1 C6 C5 -176.41(13) . . . . ?
C2 C1 C6 C7 -178.05(14) . . . . ?
N1 C1 C6 C7 2.45(15) . . . . ?
C5 C6 C7 C8 176.93(16) . . . . ?
C1 C6 C7 C8 -1.72(16) . . . . ?
C5 C6 C7 C19 -6.1(2) . . . . ?
C1 C6 C7 C19 175.23(13) . . . . ?
C6 C7 C8 N1 0.29(15) . . . . ?
C19 C7 C8 N1 -176.45(13) . . . . ?
C6 C7 C8 C9 175.39(14) . . . . ?
C19 C7 C8 C9 -1.4(3) . . . . ?
C12 N1 C8 C7 -172.82(13) . . . . ?
C1 N1 C8 C7 1.23(15) . . . . ?
C12 N1 C8 C9 11.2(2) . . . . ?
C1 N1 C8 C9 -174.73(12) . . . . ?
C13 C9 C8 C7 -7.5(2) . . . . ?
C10 C9 C8 C7 174.41(15) . . . . ?
C13 C9 C8 N1 167.24(13) . . . . ?
C10 C9 C8 N1 -10.85(19) . . . . ?
C13 C9 C10 C16 -0.4(2) . . . . ?
C8 C9 C10 C16 177.72(15) . . . . ?
C13 C9 C10 C11 175.11(14) . . . . ?
C8 C9 C10 C11 -6.8(2) . . . . ?
C16 C10 C11 C12 -161.46(16) . . . . ?
C9 C10 C11 C12 23.1(2) . . . . ?
C16 C10 C11 C18 -38.2(2) . . . . ?
C9 C10 C11 C18 146.34(15) . . . . ?
C16 C10 C11 C17 81.8(2) . . . . ?
C9 C10 C11 C17 -93.65(17) . . . . ?
C1 N1 C12 O1 8.9(2) . . . . ?
C8 N1 C12 O1 -178.07(15) . . . . ?
C1 N1 C12 C11 -166.69(14) . . . . ?
C8 N1 C12 C11 6.4(2) . . . . ?
C10 C11 C12 O1 162.10(16) . . . . ?
C18 C11 C12 O1 36.2(2) . . . . ?
C17 C11 C12 O1 -79.3(2) . . . . ?
C10 C11 C12 N1 -22.4(2) . . . . ?
C18 C11 C12 N1 -148.36(15) . . . . ?
C17 C11 C12 N1 96.13(16) . . . . ?
C10 C9 C13 C14 0.3(2) . . . . ?
C8 C9 C13 C14 -177.83(15) . . . . ?
C9 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C14 C15 C16 C10 0.4(3) . . . . ?
C9 C10 C16 C15 0.1(3) . . . . ?
C11 C10 C16 C15 -175.50(18) . . . . ?
C8 C7 C19 C24 -73.8(2) . . . . ?
C6 C7 C19 C24 109.94(17) . . . . ?
C8 C7 C19 C20 106.16(18) . . . . ?
C6 C7 C19 C20 -70.11(19) . . . . ?
C24 C19 C20 C21 2.7(2) . . . . ?
C7 C19 C20 C21 -177.23(15) . . . . ?
C19 C20 C21 C22 -1.5(3) . . . . ?
C20 C21 C22 C23 -0.4(3) . . . . ?
C21 C22 C23 C24 1.0(3) . . . . ?
C22 C23 C24 C19 0.2(3) . . . . ?
C20 C19 C24 C23 -2.1(2) . . . . ?
C7 C19 C24 C23 177.86(15) . . . . ?

_refine_diff_density_max         0.138
_refine_diff_density_min         -0.110
_refine_diff_density_rms         0.026

