# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_gl150527
_audit_block_doi                 10.5517/cc1j7tsc
_database_code_depnum_ccdc_archive 'CCDC 1407703'
_audit_update_record             
;
2015-06-19 deposited with the CCDC.
2015-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-(2-chlorophenyl)-2,5-diphenylpentane-1,5-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H19 Cl O2'
_chemical_formula_sum            'C23 H19 Cl O2'
_chemical_formula_weight         362.83

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'


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                   28.386(7)
_cell_length_b                   9.195(2)
_cell_length_c                   17.591(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 125.324(8)
_cell_angle_gamma                90.00
_cell_volume                     3746.2(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5765
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      26.84

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_process_details   sadabs

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12954
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         27.54
_reflns_number_total             4232
_reflns_number_gt                2961
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0634P)²+1.6167P] 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       ?
_refine_ls_number_reflns         4232
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1529
_refine_ls_wR_factor_gt          0.1378
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.24520(9) 0.2103(2) 0.12050(13) 0.0565(5) Uani 1 1 d . . .
C2 C 0.28778(10) 0.1763(2) 0.10748(15) 0.0690(6) Uani 1 1 d . . .
H2 H 0.2885 0.0846 0.0859 0.083 Uiso 1 1 calc R . .
C3 C 0.32862(10) 0.2774(3) 0.12636(15) 0.0727(6) Uani 1 1 d . . .
H3 H 0.3571 0.2540 0.1176 0.087 Uiso 1 1 calc R . .
C4 C 0.32779(9) 0.4127(2) 0.15802(15) 0.0646(5) Uani 1 1 d . . .
H4 H 0.3556 0.4812 0.1708 0.077 Uiso 1 1 calc R . .
C5 C 0.28542(8) 0.4474(2) 0.17100(13) 0.0545(5) Uani 1 1 d . . .
H5 H 0.2852 0.5394 0.1927 0.065 Uiso 1 1 calc R . .
C6 C 0.24313(7) 0.34732(18) 0.15231(12) 0.0473(4) Uani 1 1 d . . .
C7 C 0.19780(8) 0.38771(18) 0.16819(12) 0.0479(4) Uani 1 1 d . . .
C8 C 0.17037(7) 0.53786(17) 0.13437(11) 0.0416(4) Uani 1 1 d . . .
H8 H 0.2000 0.6088 0.1764 0.050 Uiso 1 1 calc R . .
C9 C 0.15386(7) 0.57112(17) 0.03746(12) 0.0432(4) Uani 1 1 d . . .
C10 C 0.11034(9) 0.4945(2) -0.03853(13) 0.0598(5) Uani 1 1 d . . .
H10 H 0.0915 0.4201 -0.0303 0.072 Uiso 1 1 calc R . .
C11 C 0.09471(12) 0.5280(4) -0.12704(16) 0.0944(10) Uani 1 1 d . . .
H11 H 0.0650 0.4765 -0.1781 0.113 Uiso 1 1 calc R . .
C12 C 0.12267(19) 0.6368(5) -0.1402(2) 0.1167(14) Uani 1 1 d . . .
H12 H 0.1122 0.6587 -0.1997 0.140 Uiso 1 1 calc R . .
C13 C 0.16594(15) 0.7120(3) -0.0648(3) 0.0992(11) Uani 1 1 d . . .
H13 H 0.1854 0.7847 -0.0731 0.119 Uiso 1 1 calc R . .
C14 C 0.18119(9) 0.6814(2) 0.02335(16) 0.0634(5) Uani 1 1 d . . .
H14 H 0.2101 0.7354 0.0738 0.076 Uiso 1 1 calc R . .
C15 C 0.11999(8) 0.55868(18) 0.14295(13) 0.0482(4) Uani 1 1 d . . .
H15A H 0.0882 0.4962 0.0984 0.058 Uiso 1 1 calc R . .
H15B H 0.1321 0.5305 0.2049 0.058 Uiso 1 1 calc R . .
C16 C 0.09987(7) 0.71515(17) 0.12520(12) 0.0455(4) Uani 1 1 d . . .
H16A H 0.0884 0.7426 0.0634 0.055 Uiso 1 1 calc R . .
H16B H 0.1321 0.7766 0.1697 0.055 Uiso 1 1 calc R . .
C17 C 0.04999(8) 0.7442(2) 0.13219(13) 0.0537(5) Uani 1 1 d . . .
C18 C 0.03171(8) 0.8979(2) 0.12713(12) 0.0540(5) Uani 1 1 d . . .
C19 C -0.01526(10) 0.9250(3) 0.13112(18) 0.0846(8) Uani 1 1 d . . .
H19 H -0.0349 0.8478 0.1352 0.101 Uiso 1 1 calc R . .
C20 C -0.03254(14) 1.0651(4) 0.1290(2) 0.1113(11) Uani 1 1 d . . .
H20 H -0.0643 1.0824 0.1304 0.134 Uiso 1 1 calc R . .
C21 C -0.00339(14) 1.1797(4) 0.12475(18) 0.1017(11) Uani 1 1 d . . .
H21 H -0.0148 1.2745 0.1249 0.122 Uiso 1 1 calc R . .
C22 C 0.04239(11) 1.1554(3) 0.12030(17) 0.0822(7) Uani 1 1 d . . .
H22 H 0.0620 1.2334 0.1171 0.099 Uiso 1 1 calc R . .
C23 C 0.05971(9) 1.0138(2) 0.12061(14) 0.0636(5) Uani 1 1 d . . .
H23 H 0.0905 0.9975 0.1164 0.076 Uiso 1 1 calc R . .
Cl1 Cl 0.19287(3) 0.08009(6) 0.09099(5) 0.0872(3) Uani 1 1 d . . .
O1 O 0.18521(7) 0.30667(15) 0.20770(12) 0.0779(5) Uani 1 1 d . . .
O2 O 0.02574(8) 0.6451(2) 0.14182(15) 0.0941(6) Uani 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
C1 C2 1.390(3) . ?
C1 C6 1.393(2) . ?
C1 Cl1 1.737(2) . ?
C2 C3 1.369(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.512(2) . ?
C7 O1 1.206(2) . ?
C7 C8 1.527(2) . ?
C8 C9 1.515(2) . ?
C8 C15 1.534(2) . ?
C8 H8 0.9800 . ?
C9 C10 1.379(3) . ?
C9 C14 1.384(3) . ?
C10 C11 1.385(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.378(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.513(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.514(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O2 1.211(2) . ?
C17 C18 1.491(3) . ?
C18 C23 1.373(3) . ?
C18 C19 1.398(3) . ?
C19 C20 1.371(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.368(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.365(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.390(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

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 120.8(2) . . ?
C2 C1 Cl1 118.05(16) . . ?
C6 C1 Cl1 121.05(15) . . ?
C3 C2 C1 120.15(19) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 121.43(18) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 117.46(17) . . ?
C5 C6 C7 120.24(15) . . ?
C1 C6 C7 122.29(17) . . ?
O1 C7 C6 121.47(15) . . ?
O1 C7 C8 121.95(16) . . ?
C6 C7 C8 116.55(14) . . ?
C9 C8 C7 112.16(13) . . ?
C9 C8 C15 112.71(13) . . ?
C7 C8 C15 111.65(14) . . ?
C9 C8 H8 106.6 . . ?
C7 C8 H8 106.6 . . ?
C15 C8 H8 106.6 . . ?
C10 C9 C14 118.81(18) . . ?
C10 C9 C8 120.57(17) . . ?
C14 C9 C8 120.60(17) . . ?
C9 C10 C11 120.1(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 119.1(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 120.8(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C9 120.5(3) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C16 C15 C8 111.14(14) . . ?
C16 C15 H15A 109.4 . . ?
C8 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C8 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 C17 114.22(15) . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
O2 C17 C18 121.02(17) . . ?
O2 C17 C16 120.82(17) . . ?
C18 C17 C16 118.16(17) . . ?
C23 C18 C19 118.7(2) . . ?
C23 C18 C17 122.86(16) . . ?
C19 C18 C17 118.4(2) . . ?
C20 C19 C18 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 120.5(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C22 C21 C20 120.2(2) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 120.0(3) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C18 C23 C22 120.4(2) . . ?
C18 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.039
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane/CH2Cl2'
