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

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#                                CCDC 
# 
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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_aw71m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
2-(4-methoxybenzoyl)-3-(4-nitrophenyl)spiro[cyclopropane-1,3'-indolin]-2'-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 N2 O5'
_chemical_formula_weight         414.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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   'P2(1)/n  '

loop_
_symmetry_equiv_pos_as_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                   10.2802(8)
_cell_length_b                   11.3015(9)
_cell_length_c                   18.0590(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.2340(10)
_cell_angle_gamma                90.00
_cell_volume                     2033.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9047
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.97

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9616
_exptl_absorpt_correction_T_max  0.9857
_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            18960
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_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         2.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3579
_reflns_number_gt                3164
_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)+(0.0554P)²+0.4730P] 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         3579
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.1000
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
O2 O 0.50394(11) 0.37031(9) 0.15954(7) 0.0611(3) Uani 1 1 d . . .
O1 O 0.95105(11) 0.61050(10) 0.16079(6) 0.0578(3) Uani 1 1 d . . .
C19 C 0.90059(14) 0.33918(12) 0.12947(8) 0.0437(3) Uani 1 1 d . . .
C1 C 0.77538(12) 0.48686(11) 0.28988(7) 0.0400(3) Uani 1 1 d . . .
N1 N 0.93381(13) 0.62498(11) 0.28484(7) 0.0479(3) Uani 1 1 d . . .
C12 C 0.47192(13) 0.57395(12) 0.13426(8) 0.0415(3) Uani 1 1 d . . .
C22 C 1.12322(14) 0.28431(13) 0.07765(8) 0.0465(3) Uani 1 1 d . . .
C8 C 0.79887(12) 0.48572(11) 0.21240(7) 0.0394(3) Uani 1 1 d . . .
C9 C 0.69239(13) 0.47055(12) 0.13634(8) 0.0428(3) Uani 1 1 d . . .
H9 H 0.7072 0.5160 0.0929 0.051 Uiso 1 1 calc R . .
O5 O 1.31666(12) 0.17868(11) 0.08196(7) 0.0689(3) Uani 1 1 d . . .
C11 C 0.55014(13) 0.46319(12) 0.14295(8) 0.0442(3) Uani 1 1 d . . .
C6 C 0.86026(13) 0.57241(11) 0.33174(8) 0.0425(3) Uani 1 1 d . . .
C15 C 0.32402(15) 0.78148(13) 0.12939(9) 0.0499(4) Uani 1 1 d . . .
C7 C 0.90460(13) 0.57899(12) 0.21346(8) 0.0423(3) Uani 1 1 d . . .
N2 N 1.24575(13) 0.26098(12) 0.05261(7) 0.0557(3) Uani 1 1 d . . .
O3 O 0.26260(12) 0.88793(11) 0.12794(8) 0.0742(4) Uani 1 1 d . . .
C17 C 0.34343(14) 0.57259(13) 0.14682(8) 0.0474(3) Uani 1 1 d . . .
H17 H 0.3069 0.5009 0.1570 0.057 Uiso 1 1 calc R . .
C2 C 0.69785(15) 0.41852(14) 0.32605(9) 0.0514(4) Uani 1 1 d . . .
H2 H 0.6420 0.3597 0.2996 0.062 Uiso 1 1 calc R . .
C13 C 0.52336(14) 0.68238(13) 0.11783(8) 0.0472(3) Uani 1 1 d . . .
H13 H 0.6085 0.6854 0.1087 0.057 Uiso 1 1 calc R . .
C10 C 0.78843(13) 0.37284(12) 0.16414(8) 0.0426(3) Uani 1 1 d . . .
H10 H 0.7489 0.3057 0.1851 0.051 Uiso 1 1 calc R . .
C16 C 0.26919(14) 0.67446(14) 0.14451(9) 0.0519(4) Uani 1 1 d . . .
H16 H 0.1836 0.6717 0.1529 0.062 Uiso 1 1 calc R . .
C21 C 1.11373(16) 0.24104(15) 0.14718(9) 0.0573(4) Uani 1 1 d . . .
H21 H 1.1815 0.1941 0.1764 0.069 Uiso 1 1 calc R . .
C14 C 0.45053(15) 0.78459(13) 0.11492(9) 0.0514(4) Uani 1 1 d . . .
H14 H 0.4858 0.8560 0.1033 0.062 Uiso 1 1 calc R . .
C5 C 0.86814(16) 0.59400(14) 0.40755(9) 0.0551(4) Uani 1 1 d . . .
H5 H 0.9250 0.6519 0.4344 0.066 Uiso 1 1 calc R . .
C24 C 0.91044(16) 0.37597(14) 0.05824(8) 0.0547(4) Uani 1 1 d . . .
H24 H 0.8406 0.4192 0.0275 0.066 Uiso 1 1 calc R . .
C20 C 1.00188(16) 0.26870(15) 0.17266(9) 0.0560(4) Uani 1 1 d . . .
H20 H 0.9940 0.2397 0.2196 0.067 Uiso 1 1 calc R . .
O4 O 1.27119(14) 0.32497(14) 0.00376(8) 0.0829(4) Uani 1 1 d . . .
C4 C 0.78814(17) 0.52623(16) 0.44247(9) 0.0629(4) Uani 1 1 d . . .
H4 H 0.7903 0.5393 0.4936 0.075 Uiso 1 1 calc R . .
C3 C 0.70526(16) 0.43960(16) 0.40245(9) 0.0617(4) Uani 1 1 d . . .
H3 H 0.6533 0.3945 0.4273 0.074 Uiso 1 1 calc R . .
C23 C 1.02222(16) 0.34977(14) 0.03172(8) 0.0550(4) Uani 1 1 d . . .
H23 H 1.0290 0.3758 -0.0161 0.066 Uiso 1 1 calc R . .
C18 C 0.1348(2) 0.8913(2) 0.1434(2) 0.1256(11) Uani 1 1 d . . .
H18A H 0.0750 0.8398 0.1086 0.188 Uiso 1 1 calc R . .
H18B H 0.1007 0.9707 0.1372 0.188 Uiso 1 1 calc R . .
H18C H 0.1417 0.8656 0.1949 0.188 Uiso 1 1 calc R . .
H1N H 0.9874(18) 0.6819(16) 0.2990(10) 0.064(5) Uiso 1 1 d . . .


_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
O2 C11 1.2195(17) . ?
O1 C7 1.2176(16) . ?
C19 C24 1.379(2) . ?
C19 C20 1.388(2) . ?
C19 C10 1.4904(19) . ?
C1 C2 1.3836(19) . ?
C1 C6 1.3939(19) . ?
C1 C8 1.4774(18) . ?
N1 C7 1.3534(19) . ?
N1 C6 1.3989(18) . ?
N1 H1N 0.845(19) . ?
C12 C17 1.3943(19) . ?
C12 C13 1.3952(19) . ?
C12 C11 1.4751(19) . ?
C22 C21 1.373(2) . ?
C22 C23 1.375(2) . ?
C22 N2 1.4632(19) . ?
C8 C7 1.5109(18) . ?
C8 C10 1.5338(18) . ?
C8 C9 1.5411(18) . ?
C9 C10 1.4841(18) . ?
C9 C11 1.4986(19) . ?
C9 H9 0.9800 . ?
O5 N2 1.2196(17) . ?
C6 C5 1.373(2) . ?
C15 O3 1.3559(18) . ?
C15 C14 1.388(2) . ?
C15 C16 1.390(2) . ?
N2 O4 1.2179(18) . ?
O3 C18 1.409(2) . ?
C17 C16 1.376(2) . ?
C17 H17 0.9300 . ?
C2 C3 1.384(2) . ?
C2 H2 0.9300 . ?
C13 C14 1.371(2) . ?
C13 H13 0.9300 . ?
C10 H10 0.9800 . ?
C16 H16 0.9300 . ?
C21 C20 1.375(2) . ?
C21 H21 0.9300 . ?
C14 H14 0.9300 . ?
C5 C4 1.384(2) . ?
C5 H5 0.9300 . ?
C24 C23 1.381(2) . ?
C24 H24 0.9300 . ?
C20 H20 0.9300 . ?
C4 C3 1.380(2) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C23 H23 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C24 C19 C20 118.69(13) . . ?
C24 C19 C10 123.83(12) . . ?
C20 C19 C10 117.46(13) . . ?
C2 C1 C6 119.19(13) . . ?
C2 C1 C8 133.59(13) . . ?
C6 C1 C8 107.06(11) . . ?
C7 N1 C6 112.78(12) . . ?
C7 N1 H1N 123.8(12) . . ?
C6 N1 H1N 123.3(12) . . ?
C17 C12 C13 117.91(12) . . ?
C17 C12 C11 119.13(12) . . ?
C13 C12 C11 122.87(12) . . ?
C21 C22 C23 122.04(14) . . ?
C21 C22 N2 118.59(13) . . ?
C23 C22 N2 119.37(13) . . ?
C1 C8 C7 105.46(11) . . ?
C1 C8 C10 122.72(11) . . ?
C7 C8 C10 122.48(11) . . ?
C1 C8 C9 126.83(11) . . ?
C7 C8 C9 116.10(11) . . ?
C10 C8 C9 57.72(8) . . ?
C10 C9 C11 120.85(12) . . ?
C10 C9 C8 60.89(9) . . ?
C11 C9 C8 115.36(11) . . ?
C10 C9 H9 116.1 . . ?
C11 C9 H9 116.1 . . ?
C8 C9 H9 116.1 . . ?
O2 C11 C12 121.43(12) . . ?
O2 C11 C9 120.94(13) . . ?
C12 C11 C9 117.48(12) . . ?
C5 C6 C1 122.65(13) . . ?
C5 C6 N1 128.31(13) . . ?
C1 C6 N1 109.01(12) . . ?
O3 C15 C14 115.29(14) . . ?
O3 C15 C16 124.51(14) . . ?
C14 C15 C16 120.20(13) . . ?
O1 C7 N1 126.43(13) . . ?
O1 C7 C8 127.82(13) . . ?
N1 C7 C8 105.69(11) . . ?
O4 N2 O5 123.77(14) . . ?
O4 N2 C22 118.12(13) . . ?
O5 N2 C22 118.10(14) . . ?
C15 O3 C18 118.19(15) . . ?
C16 C17 C12 121.76(13) . . ?
C16 C17 H17 119.1 . . ?
C12 C17 H17 119.1 . . ?
C3 C2 C1 118.53(14) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C14 C13 C12 121.09(13) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C9 C10 C19 124.53(12) . . ?
C9 C10 C8 61.39(9) . . ?
C19 C10 C8 119.85(11) . . ?
C9 C10 H10 113.7 . . ?
C19 C10 H10 113.7 . . ?
C8 C10 H10 113.7 . . ?
C17 C16 C15 119.04(13) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C22 C21 C20 118.57(14) . . ?
C22 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
C13 C14 C15 119.98(13) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C6 C5 C4 117.38(14) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
C19 C24 C23 121.12(13) . . ?
C19 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
C21 C20 C19 121.04(14) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C3 C4 C5 120.90(15) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C3 C2 121.33(15) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C22 C23 C24 118.39(14) . . ?
C22 C23 H23 120.8 . . ?
C24 C23 H23 120.8 . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.041

_database_code_depnum_ccdc_archive 'CCDC 1016218'
