# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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. 
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data_a51209b
_database_code_depnum_ccdc_archive 'CCDC 1465987'
_audit_update_record             
;
2016-03-14 deposited with the CCDC.
2016-06-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        6-phenylpyrrolo[1,2-b]isoquinolin-10(5H)-one
_chemical_name_common            'compound 3j'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 N O'
_chemical_formula_weight         259.29

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                   10.016(4)
_cell_length_b                   9.223(3)
_cell_length_c                   13.978(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.662(4)
_cell_angle_gamma                90
_cell_volume                     1287.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    803
_cell_measurement_theta_min      2.648
_cell_measurement_theta_max      25.616

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.328
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5708
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.040
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2525
_reflns_number_gt                1681
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0710P)²] 
 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     SHELXL
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2525
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1156
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_restrained_S_all      0.927
_refine_ls_shift/su_max          0.002
_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 0.58593(12) 0.16747(14) 0.48328(8) 0.0431(4) Uani 1 1 d . . . . .
O1 O 0.60711(14) 0.30673(15) 0.72223(8) 0.0759(4) Uani 1 1 d . . . . .
C1 C 0.67497(16) 0.08768(19) 0.43898(11) 0.0533(5) Uani 1 1 d . . . . .
H1 H 0.6656 0.0577 0.3753 0.064 Uiso 1 1 calc R U . . .
C2 C 0.78211(17) 0.0580(2) 0.50366(12) 0.0601(5) Uani 1 1 d . . . . .
H2 H 0.8580 0.0051 0.4915 0.072 Uiso 1 1 calc R U . . .
C3 C 0.75661(17) 0.1208(2) 0.59010(13) 0.0571(5) Uani 1 1 d . . . . .
H3 H 0.8118 0.1168 0.6468 0.069 Uiso 1 1 calc R U . . .
C4 C 0.63500(16) 0.19047(18) 0.57721(11) 0.0465(4) Uani 1 1 d . . . . .
C5 C 0.56658(17) 0.28644(18) 0.63758(11) 0.0506(4) Uani 1 1 d . . . . .
C6 C 0.44666(16) 0.36249(17) 0.59349(11) 0.0458(4) Uani 1 1 d . . . . .
C7 C 0.38580(18) 0.46704(19) 0.64650(12) 0.0577(5) Uani 1 1 d . . . . .
H7 H 0.4231 0.4909 0.7076 0.069 Uiso 1 1 calc R U . . .
C8 C 0.27111(19) 0.5358(2) 0.60991(13) 0.0633(5) Uani 1 1 d . . . . .
H8 H 0.2337 0.6099 0.6441 0.076 Uiso 1 1 calc R U . . .
C9 C 0.21216(18) 0.49324(19) 0.52146(12) 0.0578(5) Uani 1 1 d . . . . .
H9 H 0.1324 0.5368 0.4979 0.069 Uiso 1 1 calc R U . . .
C10 C 0.26854(16) 0.38750(17) 0.46691(11) 0.0466(4) Uani 1 1 d . . . . .
C11 C 0.39063(15) 0.32500(16) 0.50151(10) 0.0416(4) Uani 1 1 d . . . . .
C12 C 0.45694(15) 0.21688(17) 0.44064(10) 0.0449(4) Uani 1 1 d . . . . .
H12A H 0.3983 0.1338 0.4297 0.054 Uiso 1 1 calc R U . . .
H12B H 0.4691 0.2604 0.3788 0.054 Uiso 1 1 calc R U . . .
C13 C 0.19272(16) 0.33554(17) 0.37665(11) 0.0471(4) Uani 1 1 d . . . . .
C14 C 0.23852(18) 0.3536(2) 0.28673(12) 0.0562(5) Uani 1 1 d . . . . .
H14 H 0.3179 0.4036 0.2805 0.067 Uiso 1 1 calc R U . . .
C15 C 0.1676(2) 0.2980(2) 0.20616(13) 0.0655(5) Uani 1 1 d . . . . .
H15 H 0.1991 0.3115 0.1460 0.079 Uiso 1 1 calc R U . . .
C16 C 0.0507(2) 0.2228(2) 0.21434(15) 0.0699(6) Uani 1 1 d . . . . .
H16 H 0.0045 0.1831 0.1602 0.084 Uiso 1 1 calc R U . . .
C17 C 0.00248(19) 0.2065(2) 0.30301(15) 0.0710(6) Uani 1 1 d . . . . .
H17 H -0.0777 0.1575 0.3087 0.085 Uiso 1 1 calc R U . . .
C18 C 0.07275(17) 0.2626(2) 0.38339(14) 0.0581(5) Uani 1 1 d . . . . .
H18 H 0.0393 0.2513 0.4431 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 C1 1.345(2) . ?
N1 C4 1.3805(19) . ?
N1 C12 1.4515(19) . ?
O1 C5 1.2336(19) . ?
C1 C2 1.374(2) . ?
C2 C3 1.383(3) . ?
C3 C4 1.376(2) . ?
C4 C5 1.435(2) . ?
C5 C6 1.481(2) . ?
C6 C7 1.387(2) . ?
C6 C11 1.404(2) . ?
C7 C8 1.374(3) . ?
C8 C9 1.383(2) . ?
C9 C10 1.386(2) . ?
C10 C11 1.402(2) . ?
C10 C13 1.498(2) . ?
C11 C12 1.500(2) . ?
C13 C14 1.383(2) . ?
C13 C18 1.387(2) . ?
C14 C15 1.381(3) . ?
C15 C16 1.373(3) . ?
C16 C17 1.375(3) . ?
C17 C18 1.377(3) . ?

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
C1 N1 C4 108.89(13) . . ?
C1 N1 C12 125.72(13) . . ?
C4 N1 C12 125.35(13) . . ?
N1 C1 C2 108.53(15) . . ?
C1 C2 C3 107.56(16) . . ?
C4 C3 C2 107.81(15) . . ?
C3 C4 N1 107.21(15) . . ?
C3 C4 C5 132.14(15) . . ?
N1 C4 C5 120.26(14) . . ?
O1 C5 C4 121.46(16) . . ?
O1 C5 C6 121.32(16) . . ?
C4 C5 C6 117.21(13) . . ?
C7 C6 C11 120.02(16) . . ?
C7 C6 C5 118.92(14) . . ?
C11 C6 C5 120.99(14) . . ?
C8 C7 C6 120.83(16) . . ?
C7 C8 C9 119.01(17) . . ?
C8 C9 C10 121.88(16) . . ?
C9 C10 C11 118.84(15) . . ?
C9 C10 C13 119.16(15) . . ?
C11 C10 C13 121.84(14) . . ?
C10 C11 C6 119.17(14) . . ?
C10 C11 C12 119.44(13) . . ?
C6 C11 C12 121.38(14) . . ?
N1 C12 C11 113.33(12) . . ?
C14 C13 C18 118.25(16) . . ?
C14 C13 C10 122.99(15) . . ?
C18 C13 C10 118.74(15) . . ?
C15 C14 C13 120.67(18) . . ?
C16 C15 C14 120.35(19) . . ?
C15 C16 C17 119.66(18) . . ?
C16 C17 C18 120.04(18) . . ?
C17 C18 C13 120.99(17) . . ?

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
C4 N1 C1 C2 0.16(19) . . . . ?
C12 N1 C1 C2 -177.68(15) . . . . ?
N1 C1 C2 C3 0.5(2) . . . . ?
C1 C2 C3 C4 -0.9(2) . . . . ?
C2 C3 C4 N1 1.02(19) . . . . ?
C2 C3 C4 C5 -171.60(17) . . . . ?
C1 N1 C4 C3 -0.74(18) . . . . ?
C12 N1 C4 C3 177.12(14) . . . . ?
C1 N1 C4 C5 172.93(14) . . . . ?
C12 N1 C4 C5 -9.2(2) . . . . ?
C3 C4 C5 O1 -9.5(3) . . . . ?
N1 C4 C5 O1 178.68(15) . . . . ?
C3 C4 C5 C6 169.33(17) . . . . ?
N1 C4 C5 C6 -2.5(2) . . . . ?
O1 C5 C6 C7 5.3(2) . . . . ?
C4 C5 C6 C7 -173.53(14) . . . . ?
O1 C5 C6 C11 -171.45(15) . . . . ?
C4 C5 C6 C11 9.7(2) . . . . ?
C11 C6 C7 C8 -0.4(3) . . . . ?
C5 C6 C7 C8 -177.22(15) . . . . ?
C6 C7 C8 C9 3.9(3) . . . . ?
C7 C8 C9 C10 -2.8(3) . . . . ?
C8 C9 C10 C11 -1.7(3) . . . . ?
C8 C9 C10 C13 173.75(16) . . . . ?
C9 C10 C11 C6 5.1(2) . . . . ?
C13 C10 C11 C6 -170.25(14) . . . . ?
C9 C10 C11 C12 -176.39(14) . . . . ?
C13 C10 C11 C12 8.3(2) . . . . ?
C7 C6 C11 C10 -4.1(2) . . . . ?
C5 C6 C11 C10 172.62(14) . . . . ?
C7 C6 C11 C12 177.44(14) . . . . ?
C5 C6 C11 C12 -5.8(2) . . . . ?
C1 N1 C12 C11 -169.85(14) . . . . ?
C4 N1 C12 C11 12.6(2) . . . . ?
C10 C11 C12 N1 176.78(13) . . . . ?
C6 C11 C12 N1 -4.8(2) . . . . ?
C9 C10 C13 C14 116.81(18) . . . . ?
C11 C10 C13 C14 -67.8(2) . . . . ?
C9 C10 C13 C18 -65.0(2) . . . . ?
C11 C10 C13 C18 110.39(18) . . . . ?
C18 C13 C14 C15 -1.1(3) . . . . ?
C10 C13 C14 C15 177.13(15) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C17 1.8(3) . . . . ?
C15 C16 C17 C18 -1.4(3) . . . . ?
C16 C17 C18 C13 -0.2(3) . . . . ?
C14 C13 C18 C17 1.5(3) . . . . ?
C10 C13 C18 C17 -176.83(16) . . . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-2



