# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# 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_ax68
_database_code_depnum_ccdc_archive 'CCDC 1037568'
_audit_update_record             
;
2014-12-04 deposited with the CCDC.
2015-12-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
3'-(4-methoxyphenyl)-4'-nitro-5'-phenylspiro[indoline-3,2'-pyrrolidin]-2-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 N3 O4'
_chemical_formula_sum            'C24 H21 N3 O4'
_chemical_formula_weight         415.44

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.078(5)
_cell_length_b                   11.2600(18)
_cell_length_c                   17.936(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.626(5)
_cell_angle_gamma                90.00
_cell_volume                     4091.2(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4790
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      23.51

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1744
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9609
_exptl_absorpt_correction_T_max  0.9743
_exptl_absorpt_process_details   'Bruker AXS SADABS program'

_exptl_special_details           
; 
 Sheldrick,G.M.,(2003),University of gottingen,Germany  
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17031
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0874
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3608
_reflns_number_gt                2860
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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     
'calc w=1/[σ²(Fo²)+(0.0000P)²+1.3397P] where P=(Fo²+2Fc²)/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         3608
_refine_ls_number_parameters     322
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1387
_refine_ls_wR_factor_gt          0.1269
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.054
_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 0.15154(10) 0.93245(15) 0.62502(12) 0.0540(5) Uani 1 1 d . . .
C2 C 0.19343(11) 1.00193(18) 0.69235(13) 0.0665(6) Uani 1 1 d . . .
H2 H 0.1796 1.0743 0.7033 0.080 Uiso 1 1 calc R . .
C3 C 0.25653(12) 0.9608(2) 0.74300(13) 0.0717(6) Uani 1 1 d . . .
H3 H 0.2857 1.0063 0.7890 0.086 Uiso 1 1 calc R . .
C4 C 0.27749(11) 0.8538(2) 0.72725(13) 0.0686(6) Uani 1 1 d . . .
H4 H 0.3203 0.8277 0.7629 0.082 Uiso 1 1 calc R . .
C5 C 0.23504(10) 0.78451(18) 0.65834(12) 0.0612(5) Uani 1 1 d . . .
H5 H 0.2490 0.7124 0.6472 0.073 Uiso 1 1 calc R . .
C6 C 0.17182(9) 0.82507(15) 0.60704(11) 0.0515(5) Uani 1 1 d . . .
C7 C 0.11631(9) 0.77411(14) 0.52704(11) 0.0496(4) Uani 1 1 d . B .
C8 C 0.06143(9) 0.86787(15) 0.50515(12) 0.0522(5) Uani 1 1 d . . .
C9 C 0.13144(8) 0.75938(14) 0.45239(10) 0.0458(4) Uani 1 1 d D . .
H9 H 0.1743 0.7196 0.4746 0.055 Uiso 1 1 calc R A 1
C17 C 0.07872(9) 0.67089(15) 0.39499(11) 0.0511(4) Uani 1 1 d . B .
H17 H 0.0410 0.7148 0.3515 0.061 Uiso 1 1 calc R . .
C18 C 0.05631(9) 0.60269(15) 0.45235(12) 0.0523(5) Uani 1 1 d . . .
H18 H 0.0107 0.6258 0.4352 0.063 Uiso 1 1 calc R B .
C19 C 0.05908(9) 0.46835(15) 0.45007(12) 0.0519(5) Uani 1 1 d . B .
C20 C 0.10770(11) 0.40246(18) 0.51416(14) 0.0700(6) Uani 1 1 d . . .
H20 H 0.1402 0.4404 0.5620 0.084 Uiso 1 1 calc R B .
C21 C 0.10844(12) 0.2801(2) 0.50765(16) 0.0819(7) Uani 1 1 d . B .
H21 H 0.1413 0.2365 0.5516 0.098 Uiso 1 1 calc R . .
C22 C 0.06196(13) 0.22262(19) 0.43826(16) 0.0771(7) Uani 1 1 d . . .
H22 H 0.0632 0.1404 0.4344 0.093 Uiso 1 1 calc R B .
C23 C 0.01353(13) 0.28623(19) 0.37445(15) 0.0793(7) Uani 1 1 d . B .
H23 H -0.0184 0.2474 0.3265 0.095 Uiso 1 1 calc R . .
C24 C 0.01146(11) 0.40824(18) 0.38047(13) 0.0674(6) Uani 1 1 d . . .
H24 H -0.0225 0.4506 0.3370 0.081 Uiso 1 1 calc R B .
H1N H 0.0624(11) 1.012(2) 0.5629(15) 0.079(7) Uiso 1 1 d . . .
H2N H 0.0782(11) 0.6504(19) 0.5666(14) 0.075(7) Uiso 1 1 d . . .
N1 N 0.08554(9) 0.95409(15) 0.56437(11) 0.0596(4) Uani 1 1 d . . .
N2 N 0.09875(9) 0.65256(13) 0.53672(11) 0.0574(4) Uani 1 1 d . B .
N3 N 0.10636(10) 0.59261(17) 0.35242(13) 0.0703(5) Uani 1 1 d . . .
O1 O 0.00587(7) 0.86377(12) 0.44385(9) 0.0644(4) Uani 1 1 d . . .
O2 O 0.07710(10) 0.5906(2) 0.27541(12) 0.1228(8) Uani 1 1 d . B .
O3 O 0.15604(10) 0.53748(14) 0.39568(14) 0.0897(5) Uani 1 1 d . B .
C10 C 0.1348(3) 0.8721(4) 0.4079(4) 0.0448(13) Uani 0.79 1 d PD B 1
C11 C 0.18611(17) 0.9504(3) 0.4490(2) 0.0554(8) Uani 0.79 1 d PD B 1
H11 H 0.2193 0.9306 0.5030 0.066 Uiso 0.79 1 calc PR B 1
C12 C 0.19100(16) 1.0574(2) 0.4140(2) 0.0550(6) Uani 0.79 1 d PD B 1
H12 H 0.2265 1.1081 0.4441 0.066 Uiso 0.79 1 calc PR B 1
C13 C 0.14261(17) 1.0867(2) 0.33450(19) 0.0521(6) Uani 0.79 1 d PD B 1
C14 C 0.09248(16) 1.0067(3) 0.2894(2) 0.0789(10) Uani 0.79 1 d PD B 1
H14 H 0.0608 1.0237 0.2339 0.095 Uiso 0.79 1 calc PR B 1
C15 C 0.08958(16) 0.9025(3) 0.3266(2) 0.0700(10) Uani 0.79 1 d PD B 1
H15 H 0.0554 0.8499 0.2952 0.084 Uiso 0.79 1 calc PR B 1
C16 C 0.1875(2) 1.2797(3) 0.3386(3) 0.0895(11) Uani 0.79 1 d PD B 1
H16A H 0.1867 1.2966 0.3906 0.134 Uiso 0.79 1 calc PR B 1
H16B H 0.1765 1.3501 0.3044 0.134 Uiso 0.79 1 calc PR B 1
H16C H 0.2309 1.2533 0.3513 0.134 Uiso 0.79 1 calc PR B 1
O4 O 0.14076(10) 1.18891(16) 0.29348(12) 0.0737(6) Uani 0.79 1 d PD B 1
O4B O 0.2030(6) 1.2035(11) 0.3729(8) 0.135(4) Uiso 0.21 1 d PD B 2
C16B C 0.1527(10) 1.269(2) 0.3039(12) 0.127(9) Uiso 0.21 1 d PD B 2
H16D H 0.1309 1.2179 0.2553 0.191 Uiso 0.21 1 calc PR B 2
H16E H 0.1723 1.3346 0.2900 0.191 Uiso 0.21 1 calc PR B 2
H16F H 0.1212 1.2980 0.3199 0.191 Uiso 0.21 1 calc PR B 2
C11B C 0.2046(6) 0.9316(11) 0.4717(9) 0.055(4) Uiso 0.21 1 d PD B 2
H11B H 0.2345 0.8971 0.5230 0.066 Uiso 0.21 1 calc PR B 2
C12B C 0.2211(7) 1.0390(10) 0.4490(9) 0.077(4) Uiso 0.21 1 d PD B 2
H12B H 0.2623 1.0732 0.4824 0.093 Uiso 0.21 1 calc PR B 2
C13B C 0.1745(7) 1.0945(11) 0.3747(10) 0.066(4) Uiso 0.21 1 d PD B 2
C15B C 0.0995(8) 0.9365(12) 0.3519(9) 0.083(6) Uiso 0.21 1 d PD B 2
H15B H 0.0565 0.9078 0.3230 0.099 Uiso 0.21 1 calc PR B 2
C10B C 0.1454(10) 0.873(2) 0.4216(15) 0.046(6) Uiso 0.21 1 d PD B 2
C14B C 0.1144(7) 1.0421(12) 0.3225(9) 0.067(4) Uiso 0.21 1 d PD B 2
H14B H 0.0851 1.0750 0.2702 0.080 Uiso 0.21 1 calc PR B 2


_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 C2 1.374(3) . ?
C1 C6 1.389(3) . ?
C1 N1 1.405(3) . ?
C2 C3 1.376(3) . ?
C3 C4 1.377(3) . ?
C4 C5 1.391(3) . ?
C5 C6 1.377(3) . ?
C6 C7 1.506(2) . ?
C7 N2 1.461(2) . ?
C7 C9 1.546(3) . ?
C7 C8 1.548(2) . ?
C8 O1 1.227(2) . ?
C8 N1 1.347(2) . ?
C9 C10B 1.488(9) . ?
C9 C10 1.520(3) . ?
C9 C17 1.527(2) . ?
C17 N3 1.494(3) . ?
C17 C18 1.557(3) . ?
C18 N2 1.464(2) . ?
C18 C19 1.515(2) . ?
C19 C20 1.377(3) . ?
C19 C24 1.382(3) . ?
C20 C21 1.384(3) . ?
C21 C22 1.356(3) . ?
C22 C23 1.359(3) . ?
C23 C24 1.381(3) . ?
N3 O3 1.204(2) . ?
N3 O2 1.213(2) . ?
C10 C15 1.370(5) . ?
C10 C11 1.374(4) . ?
C11 C12 1.388(4) . ?
C12 C13 1.365(4) . ?
C13 O4 1.356(3) . ?
C13 C14 1.381(4) . ?
C14 C15 1.367(4) . ?
C16 O4 1.424(4) . ?
O4B C13B 1.401(9) . ?
O4B C16B 1.430(10) . ?
C11B C12B 1.387(9) . ?
C11B C10B 1.391(10) . ?
C12B C13B 1.397(9) . ?
C13B C14B 1.380(9) . ?
C15B C10B 1.389(10) . ?
C15B C14B 1.409(10) . ?

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 C1 C6 121.76(19) . . ?
C2 C1 N1 128.84(19) . . ?
C6 C1 N1 109.39(16) . . ?
C1 C2 C3 117.7(2) . . ?
C2 C3 C4 121.60(19) . . ?
C3 C4 C5 120.4(2) . . ?
C6 C5 C4 118.5(2) . . ?
C5 C6 C1 120.03(17) . . ?
C5 C6 C7 130.95(17) . . ?
C1 C6 C7 108.99(15) . . ?
N2 C7 C6 113.67(14) . . ?
N2 C7 C9 101.12(14) . . ?
C6 C7 C9 115.09(15) . . ?
N2 C7 C8 115.42(15) . . ?
C6 C7 C8 101.60(14) . . ?
C9 C7 C8 110.51(14) . . ?
O1 C8 N1 126.41(17) . . ?
O1 C8 C7 125.36(16) . . ?
N1 C8 C7 108.24(16) . . ?
C10B C9 C10 9.5(6) . . ?
C10B C9 C17 123.7(7) . . ?
C10 C9 C17 114.5(2) . . ?
C10B C9 C7 114.1(15) . . ?
C10 C9 C7 117.0(4) . . ?
C17 C9 C7 102.49(14) . . ?
N3 C17 C9 109.39(14) . . ?
N3 C17 C18 113.88(15) . . ?
C9 C17 C18 106.60(14) . . ?
N2 C18 C19 113.24(15) . . ?
N2 C18 C17 102.95(14) . . ?
C19 C18 C17 116.28(16) . . ?
C20 C19 C24 117.88(18) . . ?
C20 C19 C18 122.92(17) . . ?
C24 C19 C18 119.19(17) . . ?
C19 C20 C21 120.3(2) . . ?
C22 C21 C20 121.1(2) . . ?
C21 C22 C23 119.4(2) . . ?
C22 C23 C24 120.3(2) . . ?
C23 C24 C19 121.0(2) . . ?
C8 N1 C1 111.74(17) . . ?
C7 N2 C18 108.83(14) . . ?
O3 N3 O2 124.3(2) . . ?
O3 N3 C17 118.86(18) . . ?
O2 N3 C17 116.9(2) . . ?
C15 C10 C11 115.6(3) . . ?
C15 C10 C9 124.3(3) . . ?
C11 C10 C9 120.1(4) . . ?
C10 C11 C12 123.4(3) . . ?
C13 C12 C11 118.6(3) . . ?
O4 C13 C12 124.7(3) . . ?
O4 C13 C14 115.9(3) . . ?
C12 C13 C14 119.4(2) . . ?
C15 C14 C13 119.8(3) . . ?
C14 C15 C10 122.9(3) . . ?
C13 O4 C16 118.8(3) . . ?
C13B O4B C16B 106.0(15) . . ?
C12B C11B C10B 123.2(11) . . ?
C11B C12B C13B 118.4(12) . . ?
C14B C13B C12B 121.4(12) . . ?
C14B C13B O4B 133.6(13) . . ?
C12B C13B O4B 104.9(11) . . ?
C10B C15B C14B 123.6(13) . . ?
C15B C10B C11B 115.3(11) . . ?
C15B C10B C9 124.7(11) . . ?
C11B C10B C9 119.2(10) . . ?
C13B C14B C15B 116.9(12) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.033
