# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2014

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# 
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#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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#  fide research purposes only. It may contain copyright material
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data_aks_ss_b2_aug13_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            
3-Benzyl-2-(4-fluoro-phenyl)-3-(1H-pyrrol-2-yl)-2,3-dihydro-isoindol-1-one
_chemical_melting_point          ?
_chemical_formula_moiety         C25
_chemical_formula_sum            'C25 H19 F N2 O'
_chemical_formula_weight         382.42

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.384(2)
_cell_length_b                   10.889(3)
_cell_length_c                   11.239(3)
_cell_angle_alpha                65.601(4)
_cell_angle_beta                 82.825(3)
_cell_angle_gamma                74.204(2)
_cell_volume                     1006.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.084
_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_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4336
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_sigmaI/netI    0.1238
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3329
_reflns_number_gt                2300
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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     
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3329
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1760
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.2151
_refine_ls_wR_factor_gt          0.1765
_refine_ls_goodness_of_fit_ref   1.487
_refine_ls_restrained_S_all      1.487
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5199(3) 0.0528(2) 0.3379(2) 0.0451(6) Uani 1 1 d . . .
C2 C 0.6779(3) -0.0184(3) 0.3576(2) 0.0502(6) Uani 1 1 d . . .
C3 C 0.7428(4) -0.1603(3) 0.4086(3) 0.0687(8) Uani 1 1 d . . .
H3 H 0.6864 -0.2253 0.4326 0.082 Uiso 1 1 calc R . .
C4 C 0.8951(4) -0.2007(4) 0.4222(4) 0.0887(12) Uani 1 1 d . . .
H4 H 0.9427 -0.2948 0.4537 0.106 Uiso 1 1 calc R . .
C5 C 0.9775(4) -0.1028(4) 0.3895(4) 0.0860(11) Uani 1 1 d . . .
H5 H 1.0793 -0.1328 0.4021 0.103 Uiso 1 1 calc R . .
C6 C 0.9118(3) 0.0391(3) 0.3382(3) 0.0695(9) Uani 1 1 d . . .
H6 H 0.9677 0.1042 0.3160 0.083 Uiso 1 1 calc R . .
C7 C 0.7589(3) 0.0801(3) 0.3213(3) 0.0495(6) Uani 1 1 d . . .
C8 C 0.6595(2) 0.2261(2) 0.2668(2) 0.0442(6) Uani 1 1 d . . .
C9 C 0.3725(2) 0.2984(2) 0.2544(2) 0.0423(6) Uani 1 1 d . . .
C10 C 0.2651(3) 0.2815(3) 0.1915(3) 0.0641(8) Uani 1 1 d . . .
H10 H 0.2817 0.2027 0.1735 0.077 Uiso 1 1 calc R . .
C11 C 0.1328(3) 0.3831(3) 0.1554(4) 0.0772(10) Uani 1 1 d . . .
H11 H 0.0604 0.3724 0.1135 0.093 Uiso 1 1 calc R . .
C12 C 0.1102(3) 0.4978(3) 0.1818(3) 0.0630(8) Uani 1 1 d . . .
C13 C 0.2129(3) 0.5183(3) 0.2415(3) 0.0581(7) Uani 1 1 d . . .
H13 H 0.1954 0.5987 0.2571 0.070 Uiso 1 1 calc R . .
C14 C 0.3450(2) 0.4170(3) 0.2792(3) 0.0506(6) Uani 1 1 d . . .
H14 H 0.4157 0.4292 0.3216 0.061 Uiso 1 1 calc R . .
C15 C 0.6860(3) 0.3038(3) 0.1192(3) 0.0587(7) Uani 1 1 d . . .
H15A H 0.6160 0.3940 0.0893 0.070 Uiso 1 1 calc R . .
H15B H 0.7846 0.3196 0.1064 0.070 Uiso 1 1 calc R . .
C16 C 0.6713(3) 0.2298(3) 0.0352(3) 0.0575(7) Uani 1 1 d . . .
C17 C 0.7836(4) 0.1251(5) 0.0211(4) 0.1033(15) Uani 1 1 d . . .
H17 H 0.8712 0.0973 0.0660 0.124 Uiso 1 1 calc R . .
C18 C 0.7696(6) 0.0600(6) -0.0581(5) 0.142(2) Uani 1 1 d . . .
H18 H 0.8478 -0.0098 -0.0667 0.171 Uiso 1 1 calc R . .
C19 C 0.6412(6) 0.0981(5) -0.1235(4) 0.1143(17) Uani 1 1 d . . .
H19 H 0.6308 0.0541 -0.1763 0.137 Uiso 1 1 calc R . .
C20 C 0.5297(5) 0.2001(4) -0.1105(4) 0.0895(11) Uani 1 1 d . . .
H20 H 0.4418 0.2261 -0.1547 0.107 Uiso 1 1 calc R . .
C21 C 0.5432(4) 0.2670(3) -0.0328(3) 0.0673(8) Uani 1 1 d . . .
H21 H 0.4650 0.3379 -0.0263 0.081 Uiso 1 1 calc R . .
C22 C 0.6774(2) 0.3083(2) 0.3428(3) 0.0427(6) Uani 1 1 d . . .
C23 C 0.7253(3) 0.4278(3) 0.3034(3) 0.0560(7) Uani 1 1 d . . .
H23 H 0.7551 0.4792 0.2195 0.067 Uiso 1 1 calc R . .
C24 C 0.7205(3) 0.4575(3) 0.4153(3) 0.0639(8) Uani 1 1 d . . .
H24 H 0.7474 0.5322 0.4184 0.077 Uiso 1 1 calc R . .
C25 C 0.6698(3) 0.3577(3) 0.5170(3) 0.0555(7) Uani 1 1 d . . .
H25 H 0.6547 0.3527 0.6021 0.067 Uiso 1 1 calc R . .
F1 F -0.01908(18) 0.5991(2) 0.1421(2) 0.0970(8) Uani 1 1 d . . .
N1 N 0.64462(19) 0.2657(2) 0.4732(2) 0.0455(5) Uani 1 1 d . . .
H1 H 0.6132 0.1927 0.5203 0.055 Uiso 1 1 calc R . .
N2 N 0.5097(2) 0.19363(19) 0.29097(19) 0.0418(5) Uani 1 1 d . . .
O1 O 0.4138(2) -0.00085(18) 0.36231(19) 0.0566(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0642(14) 0.0442(12) 0.0270(13) -0.0110(11) 0.0020(11) -0.0198(11)
C2 0.0693(15) 0.0454(13) 0.0319(15) -0.0141(12) 0.0010(12) -0.0106(11)
C3 0.092(2) 0.0490(15) 0.055(2) -0.0186(15) -0.0029(17) -0.0042(14)
C4 0.107(3) 0.0590(19) 0.082(3) -0.026(2) -0.021(2) 0.0137(18)
C5 0.0701(19) 0.092(3) 0.084(3) -0.041(2) -0.0232(19) 0.0190(18)
C6 0.0573(15) 0.078(2) 0.073(2) -0.0337(18) -0.0112(15) -0.0043(14)
C7 0.0529(13) 0.0575(15) 0.0355(15) -0.0187(13) -0.0015(11) -0.0086(11)
C8 0.0442(12) 0.0470(13) 0.0365(15) -0.0088(12) 0.0011(11) -0.0166(10)
C9 0.0457(12) 0.0458(13) 0.0268(13) 0.0005(11) 0.0004(10) -0.0220(10)
C10 0.0664(16) 0.0606(16) 0.066(2) -0.0168(16) -0.0139(15) -0.0248(13)
C11 0.0608(16) 0.080(2) 0.084(3) -0.013(2) -0.0260(17) -0.0264(15)
C12 0.0476(14) 0.0565(16) 0.064(2) 0.0008(15) -0.0077(14) -0.0161(11)
C13 0.0541(14) 0.0512(14) 0.0577(19) -0.0096(14) -0.0028(13) -0.0136(11)
C14 0.0492(13) 0.0518(14) 0.0473(16) -0.0127(13) -0.0044(12) -0.0164(11)
C15 0.0604(15) 0.0648(17) 0.0476(19) -0.0114(15) 0.0036(13) -0.0293(13)
C16 0.0667(15) 0.0668(17) 0.0270(15) -0.0052(14) 0.0088(12) -0.0234(13)
C17 0.091(2) 0.141(4) 0.068(3) -0.056(3) -0.010(2) 0.013(2)
C18 0.173(4) 0.150(5) 0.084(3) -0.074(4) -0.025(3) 0.045(4)
C19 0.191(5) 0.095(3) 0.058(2) -0.035(2) -0.019(3) -0.023(3)
C20 0.119(3) 0.104(3) 0.051(2) -0.024(2) -0.006(2) -0.045(2)
C21 0.0834(19) 0.0693(18) 0.0403(17) -0.0085(15) -0.0032(15) -0.0250(15)
C22 0.0390(11) 0.0414(12) 0.0396(16) -0.0054(12) -0.0015(10) -0.0138(9)
C23 0.0559(14) 0.0497(14) 0.0587(19) -0.0119(14) 0.0033(13) -0.0241(11)
C24 0.0663(16) 0.0501(15) 0.083(2) -0.0294(17) -0.0060(16) -0.0204(13)
C25 0.0569(14) 0.0520(15) 0.0608(19) -0.0260(15) -0.0090(13) -0.0087(12)
F1 0.0563(10) 0.0790(13) 0.127(2) -0.0133(14) -0.0277(11) -0.0047(9)
N1 0.0486(10) 0.0410(11) 0.0429(14) -0.0095(10) -0.0058(9) -0.0138(8)
N2 0.0491(10) 0.0394(10) 0.0328(12) -0.0060(9) -0.0015(9) -0.0173(8)
O1 0.0765(11) 0.0512(10) 0.0445(12) -0.0115(9) 0.0070(9) -0.0346(9)

_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
C1 O1 1.234(3) . ?
C1 N2 1.380(3) . ?
C1 C2 1.470(4) . ?
C2 C7 1.378(4) . ?
C2 C3 1.389(4) . ?
C3 C4 1.384(5) . ?
C4 C5 1.387(5) . ?
C5 C6 1.391(5) . ?
C6 C7 1.394(4) . ?
C7 C8 1.518(3) . ?
C8 N2 1.507(3) . ?
C8 C22 1.519(3) . ?
C8 C15 1.543(4) . ?
C9 C14 1.382(3) . ?
C9 C10 1.391(3) . ?
C9 N2 1.440(3) . ?
C10 C11 1.392(4) . ?
C11 C12 1.356(4) . ?
C12 C13 1.353(4) . ?
C12 F1 1.374(3) . ?
C13 C14 1.390(3) . ?
C15 C16 1.510(4) . ?
C16 C17 1.374(5) . ?
C16 C21 1.379(4) . ?
C17 C18 1.383(5) . ?
C18 C19 1.365(7) . ?
C19 C20 1.347(6) . ?
C20 C21 1.383(4) . ?
C22 N1 1.364(3) . ?
C22 C23 1.372(3) . ?
C23 C24 1.415(4) . ?
C24 C25 1.354(4) . ?
C25 N1 1.366(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
O1 C1 N2 125.2(2) . . ?
O1 C1 C2 127.6(2) . . ?
N2 C1 C2 107.2(2) . . ?
C7 C2 C3 122.6(3) . . ?
C7 C2 C1 108.8(2) . . ?
C3 C2 C1 128.6(3) . . ?
C4 C3 C2 117.1(3) . . ?
C3 C4 C5 120.9(3) . . ?
C4 C5 C6 121.6(3) . . ?
C5 C6 C7 117.6(3) . . ?
C2 C7 C6 120.1(3) . . ?
C2 C7 C8 111.1(2) . . ?
C6 C7 C8 128.7(3) . . ?
N2 C8 C7 100.25(18) . . ?
N2 C8 C22 111.75(19) . . ?
C7 C8 C22 110.63(17) . . ?
N2 C8 C15 110.35(18) . . ?
C7 C8 C15 112.4(2) . . ?
C22 C8 C15 111.1(2) . . ?
C14 C9 C10 118.8(2) . . ?
C14 C9 N2 121.47(18) . . ?
C10 C9 N2 119.7(2) . . ?
C9 C10 C11 119.8(3) . . ?
C12 C11 C10 119.5(2) . . ?
C13 C12 C11 122.2(3) . . ?
C13 C12 F1 118.9(3) . . ?
C11 C12 F1 118.8(2) . . ?
C12 C13 C14 118.8(2) . . ?
C9 C14 C13 120.8(2) . . ?
C16 C15 C8 115.1(2) . . ?
C17 C16 C21 117.0(3) . . ?
C17 C16 C15 122.3(3) . . ?
C21 C16 C15 120.6(3) . . ?
C16 C17 C18 121.7(3) . . ?
C19 C18 C17 120.1(4) . . ?
C20 C19 C18 119.1(4) . . ?
C19 C20 C21 121.3(4) . . ?
C16 C21 C20 120.8(3) . . ?
N1 C22 C23 108.2(2) . . ?
N1 C22 C8 120.9(2) . . ?
C23 C22 C8 130.9(3) . . ?
C22 C23 C24 106.7(3) . . ?
C25 C24 C23 107.8(2) . . ?
C24 C25 N1 108.3(3) . . ?
C22 N1 C25 109.0(2) . . ?
C1 N2 C9 123.71(18) . . ?
C1 N2 C8 112.34(18) . . ?
C9 N2 C8 123.55(18) . . ?

_diffrn_measured_fraction_theta_max 0.938
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.938
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.124
_database_code_depnum_ccdc_archive 'CCDC 967591'