# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_KN-415
_database_code_depnum_ccdc_archive 'CCDC 1823989'
_audit_update_record             
;
2018-02-14 deposited with the CCDC.
2018-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        (3-Benzoylbenzofuran-2-yl)(p-tolyl)methanone
_chemical_name_common            KN-415
_chemical_melting_point          110-113
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H16 O3'
_chemical_formula_weight         340.36

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'
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                   7.6469(6)
_cell_length_b                   11.4426(8)
_cell_length_c                   19.7800(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.222(5)
_cell_angle_gamma                90
_cell_volume                     1728.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2207
_cell_measurement_theta_min      2.057
_cell_measurement_theta_max      25.000

_exptl_crystal_description       plates
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            25141
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.057
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3011
_reflns_number_gt                2207
_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 SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1000P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3011
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1521
_refine_ls_wR_factor_gt          0.1371
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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_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
O1 O 0.29267(17) 0.97372(10) 0.42538(6) 0.0572(3) Uani 1 1 d . . . . .
O2 O 0.3517(2) 0.73772(11) 0.54029(6) 0.0749(4) Uani 1 1 d . . . . .
O3 O 0.57988(19) 0.64029(12) 0.40486(7) 0.0737(4) Uani 1 1 d . . . . .
C10 C 0.3704(2) 0.78815(15) 0.40190(8) 0.0534(5) Uani 1 1 d . . . . .
C18 C 0.2928(2) 0.57117(15) 0.41452(8) 0.0533(4) Uani 1 1 d . . . . .
C5 C 0.2516(2) 0.92262(14) 0.57366(8) 0.0494(4) Uani 1 1 d . . . . .
C8 C 0.3114(2) 0.83779(15) 0.52336(8) 0.0533(4) Uani 1 1 d . . . . .
C17 C 0.4256(3) 0.66295(15) 0.40846(8) 0.0552(5) Uani 1 1 d . . . . .
C9 C 0.3251(2) 0.86323(14) 0.45088(8) 0.0532(5) Uani 1 1 d . . . . .
C6 C 0.2238(3) 1.03965(16) 0.56201(9) 0.0635(5) Uani 1 1 d . . . . .
H6 H 0.2368 1.0702 0.5190 0.076 Uiso 1 1 calc R U . . .
C16 C 0.3181(2) 0.96701(15) 0.35752(8) 0.0541(5) Uani 1 1 d . . . . .
C11 C 0.3674(2) 0.85459(15) 0.34033(9) 0.0538(4) Uani 1 1 d . . . . .
C2 C 0.1530(2) 1.07134(15) 0.67778(9) 0.0575(5) Uani 1 1 d . . . . .
C4 C 0.2277(3) 0.88063(17) 0.63834(9) 0.0683(5) Uani 1 1 d . . . . .
H4 H 0.2448 0.8016 0.6476 0.082 Uiso 1 1 calc R U . . .
C19 C 0.3453(3) 0.45757(17) 0.42884(9) 0.0638(5) Uani 1 1 d . . . . .
H19 H 0.4640 0.4406 0.4353 0.077 Uiso 1 1 calc R U . . .
C12 C 0.4003(2) 0.83033(18) 0.27294(9) 0.0619(5) Uani 1 1 d . . . . .
H12 H 0.4345 0.7561 0.2598 0.074 Uiso 1 1 calc R U . . .
C3 C 0.1792(3) 0.95398(18) 0.68876(10) 0.0722(6) Uani 1 1 d . . . . .
H3 H 0.1637 0.9234 0.7316 0.087 Uiso 1 1 calc R U . . .
C15 C 0.2986(3) 1.05691(16) 0.31181(10) 0.0660(5) Uani 1 1 d . . . . .
H15 H 0.2653 1.1315 0.3247 0.079 Uiso 1 1 calc R U . . .
C13 C 0.3804(3) 0.9195(2) 0.22701(10) 0.0701(6) Uani 1 1 d . . . . .
H13 H 0.4006 0.9052 0.1818 0.084 Uiso 1 1 calc R U . . .
C14 C 0.3307(3) 1.03078(19) 0.24628(10) 0.0722(6) Uani 1 1 d . . . . .
H14 H 0.3189 1.0892 0.2136 0.087 Uiso 1 1 calc R U . . .
C7 C 0.1765(3) 1.11265(17) 0.61384(10) 0.0691(6) Uani 1 1 d . . . . .
H7 H 0.1601 1.1918 0.6050 0.083 Uiso 1 1 calc R U . . .
C20 C 0.2247(4) 0.37011(19) 0.43358(11) 0.0788(6) Uani 1 1 d . . . . .
H20 H 0.2612 0.2941 0.4432 0.095 Uiso 1 1 calc R U . . .
C23 C 0.1152(3) 0.59454(19) 0.40482(10) 0.0703(6) Uani 1 1 d . . . . .
H23 H 0.0779 0.6703 0.3950 0.084 Uiso 1 1 calc R U . . .
C21 C 0.0493(4) 0.3953(2) 0.42411(12) 0.0870(7) Uani 1 1 d . . . . .
H21 H -0.0328 0.3359 0.4276 0.104 Uiso 1 1 calc R U . . .
C22 C -0.0060(3) 0.5068(2) 0.40963(12) 0.0840(7) Uani 1 1 d . . . . .
H22 H -0.1250 0.5230 0.4031 0.101 Uiso 1 1 calc R U . . .
C1 C 0.1049(3) 1.15123(19) 0.73397(11) 0.0789(6) Uani 1 1 d . . . . .
H1A H -0.0122 1.1342 0.7462 0.118 Uiso 1 1 calc R U . . .
H1B H 0.1111 1.2309 0.7191 0.118 Uiso 1 1 calc R U . . .
H1C H 0.1848 1.1397 0.7726 0.118 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
O1 C16 1.369(2) . ?
O1 C9 1.3785(19) . ?
O2 C8 1.2273(19) . ?
O3 C17 1.214(2) . ?
C10 C9 1.354(2) . ?
C10 C11 1.435(2) . ?
C10 C17 1.497(2) . ?
C18 C19 1.385(3) . ?
C18 C23 1.387(3) . ?
C18 C17 1.470(3) . ?
C5 C6 1.373(2) . ?
C5 C4 1.388(2) . ?
C5 C8 1.481(2) . ?
C8 C9 1.472(2) . ?
C6 C7 1.386(3) . ?
C16 C15 1.372(3) . ?
C16 C11 1.388(2) . ?
C11 C12 1.398(2) . ?
C2 C7 1.371(3) . ?
C2 C3 1.373(3) . ?
C2 C1 1.501(3) . ?
C4 C3 1.370(3) . ?
C19 C20 1.368(3) . ?
C12 C13 1.369(3) . ?
C15 C14 1.366(3) . ?
C13 C14 1.388(3) . ?
C20 C21 1.375(4) . ?
C23 C22 1.374(3) . ?
C21 C22 1.369(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
C16 O1 C9 105.95(12) . . ?
C9 C10 C11 106.18(15) . . ?
C9 C10 C17 128.84(15) . . ?
C11 C10 C17 124.85(15) . . ?
C19 C18 C23 118.66(19) . . ?
C19 C18 C17 119.58(17) . . ?
C23 C18 C17 121.75(17) . . ?
C6 C5 C4 117.70(16) . . ?
C6 C5 C8 125.26(15) . . ?
C4 C5 C8 117.00(15) . . ?
O2 C8 C9 114.82(15) . . ?
O2 C8 C5 120.69(15) . . ?
C9 C8 C5 124.48(15) . . ?
O3 C17 C18 122.01(16) . . ?
O3 C17 C10 118.00(17) . . ?
C18 C17 C10 119.87(16) . . ?
C10 C9 O1 111.59(14) . . ?
C10 C9 C8 127.31(15) . . ?
O1 C9 C8 121.09(14) . . ?
C5 C6 C7 120.53(17) . . ?
O1 C16 C15 125.99(16) . . ?
O1 C16 C11 110.34(14) . . ?
C15 C16 C11 123.67(17) . . ?
C16 C11 C12 118.90(16) . . ?
C16 C11 C10 105.94(15) . . ?
C12 C11 C10 135.16(17) . . ?
C7 C2 C3 117.22(17) . . ?
C7 C2 C1 121.55(18) . . ?
C3 C2 C1 121.21(18) . . ?
C3 C4 C5 120.91(18) . . ?
C20 C19 C18 120.8(2) . . ?
C13 C12 C11 117.75(18) . . ?
C4 C3 C2 121.80(18) . . ?
C14 C15 C16 116.26(18) . . ?
C12 C13 C14 121.56(19) . . ?
C15 C14 C13 121.86(18) . . ?
C2 C7 C6 121.83(19) . . ?
C19 C20 C21 119.6(2) . . ?
C22 C23 C18 120.6(2) . . ?
C22 C21 C20 120.8(2) . . ?
C21 C22 C23 119.6(2) . . ?

_refine_diff_density_max         0.169
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.035


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethyl acetate-Hexanes'
_chemical_compound_source        synthetic
