# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
# 
#######################################################################

data_compound_3ka
_database_code_depnum_ccdc_archive 'CCDC 1486863'
_audit_update_record             
;
2016-09-04 deposited with the CCDC.
2016-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            
2-((3-benzoylisoxazol-5-yl)methyl)isoindoline-1,3-dione
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H12 N2 O4'
_chemical_formula_sum            'C19 H12 N2 O4'
_chemical_formula_weight         332.31

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           Triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   8.066(8)
_cell_length_b                   8.242(8)
_cell_length_c                   12.157(13)
_cell_angle_alpha                92.727(13)
_cell_angle_beta                 102.604(12)
_cell_angle_gamma                98.233(11)
_cell_volume                     778.0(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1850
_cell_measurement_theta_min      1.72
_cell_measurement_theta_max      25.02

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'

_exptl_special_details           
;
 ?
;

_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  'Bruker SMART APEX-II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4051
_diffrn_reflns_av_R_equivalents  0.0128
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2700
_reflns_number_gt                2122
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0539P)²+0.0617P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       0.024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2700
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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 0.53130(17) 0.00887(16) 0.13461(10) 0.0616(4) Uani 1 1 d . . .
N2 N 0.23049(17) 0.30419(16) 0.10290(11) 0.0467(4) Uani 1 1 d . . .
O3 O -0.02777(17) 0.13830(15) 0.09478(12) 0.0688(4) Uani 1 1 d . . .
O1 O 0.68711(18) 0.14513(16) 0.50372(11) 0.0716(4) Uani 1 1 d . . .
O4 O 0.44341(16) 0.52867(18) 0.12621(14) 0.0813(5) Uani 1 1 d . . .
N1 N 0.6261(2) -0.04221(19) 0.23462(13) 0.0616(4) Uani 1 1 d . . .
C13 C 0.01238(19) 0.43382(18) 0.14012(12) 0.0406(4) Uani 1 1 d . . .
C18 C 0.1559(2) 0.55197(19) 0.15106(13) 0.0438(4) Uani 1 1 d . . .
C8 C 0.5845(2) 0.03989(19) 0.31635(14) 0.0456(4) Uani 1 1 d . . .
C12 C 0.0589(2) 0.27256(19) 0.10985(13) 0.0450(4) Uani 1 1 d . . .
C19 C 0.2978(2) 0.4705(2) 0.12649(14) 0.0505(4) Uani 1 1 d . . .
C10 C 0.4356(2) 0.11942(19) 0.16267(14) 0.0465(4) Uani 1 1 d . . .
C9 C 0.4649(2) 0.1443(2) 0.27517(14) 0.0484(4) Uani 1 1 d . . .
H9 H 0.4171 0.2146 0.3170 0.058 Uiso 1 1 calc R . .
C1 C 0.7296(2) -0.1295(2) 0.47239(14) 0.0484(4) Uani 1 1 d . . .
C14 C -0.1408(2) 0.4741(2) 0.15639(14) 0.0520(4) Uani 1 1 d . . .
H14 H -0.2370 0.3941 0.1496 0.062 Uiso 1 1 calc R . .
C11 C 0.3243(2) 0.1828(2) 0.06472(15) 0.0566(5) Uani 1 1 d . . .
H11A H 0.3951 0.2323 0.0163 0.068 Uiso 1 1 calc R . .
H11B H 0.2434 0.0921 0.0207 0.068 Uiso 1 1 calc R . .
C16 C -0.0042(3) 0.7557(2) 0.19376(16) 0.0642(5) Uani 1 1 d . . .
H16 H -0.0115 0.8650 0.2118 0.077 Uiso 1 1 calc R . .
C2 C 0.8684(2) -0.1201(3) 0.56439(15) 0.0602(5) Uani 1 1 d . . .
H2 H 0.9224 -0.0181 0.6003 0.072 Uiso 1 1 calc R . .
C7 C 0.6692(2) 0.0259(2) 0.43719(15) 0.0497(4) Uani 1 1 d . . .
C6 C 0.6491(3) -0.2816(2) 0.42090(17) 0.0620(5) Uani 1 1 d . . .
H6 H 0.5569 -0.2898 0.3587 0.074 Uiso 1 1 calc R . .
C17 C 0.1506(2) 0.7147(2) 0.17807(16) 0.0599(5) Uani 1 1 d . . .
H17 H 0.2472 0.7945 0.1856 0.072 Uiso 1 1 calc R . .
C15 C -0.1467(3) 0.6378(2) 0.18311(15) 0.0592(5) Uani 1 1 d . . .
H15 H -0.2488 0.6685 0.1940 0.071 Uiso 1 1 calc R . .
C4 C 0.8444(3) -0.4116(3) 0.5531(2) 0.0806(7) Uani 1 1 d . . .
H4 H 0.8820 -0.5065 0.5807 0.097 Uiso 1 1 calc R . .
C3 C 0.9261(3) -0.2606(3) 0.60261(19) 0.0742(6) Uani 1 1 d . . .
H3 H 1.0215 -0.2529 0.6626 0.089 Uiso 1 1 calc R . .
C5 C 0.7066(3) -0.4228(3) 0.4626(2) 0.0788(6) Uani 1 1 d . . .
H5 H 0.6512 -0.5256 0.4288 0.095 Uiso 1 1 calc R . .


_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 C10 1.352(2) . ?
O2 N1 1.405(2) . ?
N2 C12 1.393(3) . ?
N2 C19 1.392(2) . ?
N2 C11 1.454(2) . ?
O3 C12 1.204(2) . ?
O1 C7 1.214(2) . ?
O4 C19 1.204(2) . ?
N1 C8 1.305(2) . ?
C13 C14 1.376(3) . ?
C13 C18 1.380(2) . ?
C13 C12 1.483(2) . ?
C18 C17 1.375(3) . ?
C18 C19 1.483(3) . ?
C8 C9 1.410(2) . ?
C8 C7 1.496(3) . ?
C10 C9 1.337(3) . ?
C10 C11 1.491(2) . ?
C1 C6 1.379(3) . ?
C1 C2 1.389(3) . ?
C1 C7 1.484(3) . ?
C14 C15 1.382(3) . ?
C16 C15 1.373(3) . ?
C16 C17 1.389(3) . ?
C2 C3 1.373(3) . ?
C6 C5 1.391(3) . ?
C4 C3 1.366(3) . ?
C4 C5 1.372(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
C10 O2 N1 108.50(13) . . ?
C12 N2 C19 111.74(13) . . ?
C12 N2 C11 124.64(15) . . ?
C19 N2 C11 123.34(16) . . ?
C8 N1 O2 105.05(14) . . ?
C14 C13 C18 121.37(16) . . ?
C14 C13 C12 130.60(15) . . ?
C18 C13 C12 108.03(15) . . ?
C17 C18 C13 121.05(16) . . ?
C17 C18 C19 130.60(15) . . ?
C13 C18 C19 108.33(16) . . ?
N1 C8 C9 112.05(16) . . ?
N1 C8 C7 120.72(16) . . ?
C9 C8 C7 127.10(15) . . ?
O3 C12 N2 124.69(16) . . ?
O3 C12 C13 129.27(17) . . ?
N2 C12 C13 106.03(13) . . ?
O4 C19 N2 124.40(17) . . ?
O4 C19 C18 129.73(17) . . ?
N2 C19 C18 105.87(15) . . ?
C9 C10 O2 109.81(14) . . ?
C9 C10 C11 135.36(16) . . ?
O2 C10 C11 114.83(15) . . ?
C10 C9 C8 104.59(15) . . ?
C6 C1 C2 119.24(17) . . ?
C6 C1 C7 122.68(17) . . ?
C2 C1 C7 118.02(16) . . ?
C13 C14 C15 117.71(16) . . ?
N2 C11 C10 110.91(15) . . ?
C15 C16 C17 121.19(18) . . ?
C3 C2 C1 120.4(2) . . ?
O1 C7 C1 122.00(17) . . ?
O1 C7 C8 117.86(16) . . ?
C1 C7 C8 120.14(15) . . ?
C1 C6 C5 119.6(2) . . ?
C18 C17 C16 117.62(17) . . ?
C16 C15 C14 121.05(18) . . ?
C3 C4 C5 119.8(2) . . ?
C4 C3 C2 120.5(2) . . ?
C4 C5 C6 120.5(2) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.033
