# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_40723ks_0m
_database_code_depnum_ccdc_archive 'CCDC 1445574'
_audit_update_record             
;
2016-01-06 deposited with the CCDC.
2016-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        6-methoxy-9-phenyl-3H-xanthen-3-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 O3'
_chemical_formula_sum            'C20 H14 O3'
_chemical_formula_weight         302.31

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'
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   'P 21/n  '
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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                   10.307(2)
_cell_length_b                   6.9664(13)
_cell_length_c                   20.194(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.558(3)
_cell_angle_gamma                90.00
_cell_volume                     1448.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    1118
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      30.75
_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9727
_exptl_absorpt_correction_T_max  0.9954
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90
_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 APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            8676
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_sigmaI/netI    0.0664
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         27.00
_reflns_number_total             3148
_reflns_number_gt                1950
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_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)+(0.0603P)²+0.0000P] 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         3148
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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 0.23358(16) 0.3252(2) 0.22869(9) 0.0154(4) Uani 1 1 d . . .
C2 C 0.16877(17) 0.3285(2) 0.28671(10) 0.0179(4) Uani 1 1 d . . .
H2 H 0.0767 0.3362 0.2856 0.021 Uiso 1 1 calc R . .
C3 C 0.23867(16) 0.3204(3) 0.34670(9) 0.0171(4) Uani 1 1 d . . .
C4 C 0.37472(17) 0.3064(3) 0.34872(10) 0.0175(4) Uani 1 1 d . . .
H4 H 0.4227 0.3005 0.3899 0.021 Uiso 1 1 calc R . .
C5 C 0.43732(17) 0.3014(3) 0.28989(9) 0.0176(4) Uani 1 1 d . . .
H5 H 0.5293 0.2905 0.2912 0.021 Uiso 1 1 calc R . .
C6 C 0.37010(16) 0.3119(2) 0.22806(9) 0.0151(4) Uani 1 1 d . . .
C7 C 0.43008(16) 0.3031(2) 0.16505(9) 0.0154(4) Uani 1 1 d . . .
C8 C 0.35399(16) 0.3157(2) 0.10762(9) 0.0157(4) Uani 1 1 d . . .
C9 C 0.40383(17) 0.3188(3) 0.04235(9) 0.0177(4) Uani 1 1 d . . .
H9 H 0.4952 0.3149 0.0379 0.021 Uiso 1 1 calc R . .
C10 C 0.32571(17) 0.3270(3) -0.01266(10) 0.0190(4) Uani 1 1 d . . .
H10 H 0.3632 0.3297 -0.0548 0.023 Uiso 1 1 calc R . .
C11 C 0.18384(17) 0.3319(3) -0.00913(10) 0.0180(4) Uani 1 1 d . . .
C12 C 0.13314(16) 0.3396(2) 0.05608(10) 0.0176(4) Uani 1 1 d . . .
H12 H 0.0422 0.3513 0.0608 0.021 Uiso 1 1 calc R . .
C13 C 0.21364(16) 0.3302(2) 0.11057(9) 0.0158(4) Uani 1 1 d . . .
C14 C 0.23765(19) 0.3347(3) 0.46518(10) 0.0233(5) Uani 1 1 d . . .
H14A H 0.2854 0.2147 0.4731 0.035 Uiso 1 1 calc R . .
H14B H 0.1762 0.3536 0.5002 0.035 Uiso 1 1 calc R . .
H14C H 0.2989 0.4424 0.4653 0.035 Uiso 1 1 calc R . .
C15 C 0.57339(16) 0.2706(3) 0.16297(9) 0.0156(4) Uani 1 1 d . . .
C16 C 0.66188(17) 0.4103(3) 0.18484(10) 0.0213(5) Uani 1 1 d . . .
H16 H 0.6317 0.5293 0.2012 0.026 Uiso 1 1 calc R . .
C17 C 0.79432(17) 0.3754(3) 0.18269(10) 0.0237(5) Uani 1 1 d . . .
H17 H 0.8546 0.4717 0.1968 0.028 Uiso 1 1 calc R . .
C18 C 0.83877(17) 0.2012(3) 0.16012(9) 0.0211(4) Uani 1 1 d . . .
H18 H 0.9294 0.1775 0.1593 0.025 Uiso 1 1 calc R . .
C19 C 0.75138(16) 0.0613(3) 0.13865(9) 0.0196(4) Uani 1 1 d . . .
H19 H 0.7819 -0.0587 0.1233 0.023 Uiso 1 1 calc R . .
C20 C 0.61882(16) 0.0968(3) 0.13956(9) 0.0173(4) Uani 1 1 d . . .
H20 H 0.5589 0.0016 0.1241 0.021 Uiso 1 1 calc R . .
O1 O 0.15875(11) 0.33308(17) 0.17109(6) 0.0174(3) Uani 1 1 d . . .
O2 O 0.11252(12) 0.32959(19) -0.06077(7) 0.0251(3) Uani 1 1 d . . .
O3 O 0.16787(12) 0.32533(18) 0.40201(7) 0.0222(3) 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 O1 1.368(2) . ?
C1 C2 1.375(3) . ?
C1 C6 1.411(2) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
C3 O3 1.362(2) . ?
C3 C4 1.404(2) . ?
C4 C5 1.377(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.441(3) . ?
C7 C8 1.374(2) . ?
C7 C15 1.497(2) . ?
C8 C9 1.436(3) . ?
C8 C13 1.454(2) . ?
C9 C10 1.344(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.468(2) . ?
C10 H10 0.9500 . ?
C11 O2 1.249(2) . ?
C11 C12 1.439(3) . ?
C12 C13 1.350(3) . ?
C12 H12 0.9500 . ?
C13 O1 1.370(2) . ?
C14 O3 1.438(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C20 1.388(3) . ?
C15 C16 1.392(2) . ?
C16 C17 1.389(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.381(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

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
O1 C1 C2 116.56(15) . . ?
O1 C1 C6 121.32(16) . . ?
C2 C1 C6 122.11(17) . . ?
C1 C2 C3 119.48(16) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
O3 C3 C2 116.12(15) . . ?
O3 C3 C4 123.30(17) . . ?
C2 C3 C4 120.58(17) . . ?
C5 C4 C3 118.84(17) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.32(16) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C5 C6 C1 116.67(16) . . ?
C5 C6 C7 124.73(16) . . ?
C1 C6 C7 118.57(17) . . ?
C8 C7 C6 119.45(15) . . ?
C8 C7 C15 120.87(16) . . ?
C6 C7 C15 119.61(16) . . ?
C7 C8 C9 124.17(15) . . ?
C7 C8 C13 120.10(16) . . ?
C9 C8 C13 115.72(16) . . ?
C10 C9 C8 122.25(16) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C9 C10 C11 121.49(17) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
O2 C11 C12 122.71(16) . . ?
O2 C11 C10 120.64(17) . . ?
C12 C11 C10 116.65(17) . . ?
C13 C12 C11 120.60(16) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 O1 117.60(15) . . ?
C12 C13 C8 123.12(17) . . ?
O1 C13 C8 119.27(16) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 119.43(16) . . ?
C20 C15 C7 119.32(16) . . ?
C16 C15 C7 121.24(16) . . ?
C17 C16 C15 119.90(18) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C16 120.33(18) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 120.08(16) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 119.82(17) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C15 C20 C19 120.42(17) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C1 O1 C13 121.23(13) . . ?
C3 O3 C14 117.63(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 179.83(15) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C1 C2 C3 O3 179.65(15) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
O3 C3 C4 C5 179.66(16) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C4 C5 C6 C7 -178.54(16) . . . . ?
O1 C1 C6 C5 -178.94(15) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
O1 C1 C6 C7 -1.2(2) . . . . ?
C2 C1 C6 C7 178.00(16) . . . . ?
C5 C6 C7 C8 -179.73(17) . . . . ?
C1 C6 C7 C8 2.7(2) . . . . ?
C5 C6 C7 C15 3.3(3) . . . . ?
C1 C6 C7 C15 -174.32(16) . . . . ?
C6 C7 C8 C9 176.56(16) . . . . ?
C15 C7 C8 C9 -6.5(3) . . . . ?
C6 C7 C8 C13 -2.4(3) . . . . ?
C15 C7 C8 C13 174.53(15) . . . . ?
C7 C8 C9 C10 178.49(18) . . . . ?
C13 C8 C9 C10 -2.5(2) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C9 C10 C11 O2 -176.30(16) . . . . ?
C9 C10 C11 C12 3.8(3) . . . . ?
O2 C11 C12 C13 176.02(18) . . . . ?
C10 C11 C12 C13 -4.1(2) . . . . ?
C11 C12 C13 O1 -178.27(14) . . . . ?
C11 C12 C13 C8 1.2(3) . . . . ?
C7 C8 C13 C12 -178.76(17) . . . . ?
C9 C8 C13 C12 2.2(3) . . . . ?
C7 C8 C13 O1 0.7(2) . . . . ?
C9 C8 C13 O1 -178.42(14) . . . . ?
C8 C7 C15 C20 -66.8(2) . . . . ?
C6 C7 C15 C20 110.12(19) . . . . ?
C8 C7 C15 C16 114.0(2) . . . . ?
C6 C7 C15 C16 -69.1(2) . . . . ?
C20 C15 C16 C17 0.4(3) . . . . ?
C7 C15 C16 C17 179.58(18) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C16 C15 C20 C19 0.8(3) . . . . ?
C7 C15 C20 C19 -178.42(17) . . . . ?
C18 C19 C20 C15 -1.1(3) . . . . ?
C2 C1 O1 C13 -179.84(14) . . . . ?
C6 C1 O1 C13 -0.6(2) . . . . ?
C12 C13 O1 C1 -179.64(16) . . . . ?
C8 C13 O1 C1 0.9(2) . . . . ?
C2 C3 O3 C14 -174.50(15) . . . . ?
C4 C3 O3 C14 6.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_40714ks_0ma
_database_code_depnum_ccdc_archive 'CCDC 1445575'
_audit_update_record             
;
2016-01-06 deposited with the CCDC.
2016-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'6-methoxy-9-phenyl-3H-xanthen-3-one, HBr complex'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H13 O3, Br'
_chemical_formula_sum            'C19 H13 Br O3'
_chemical_formula_weight         369.20

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P n n a '
_symmetry_space_group_name_Hall  '-P 2a 2bc'
_symmetry_Int_Tables_number      52
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x+1/2, y+1/2, -z+1/2'
'x, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x-1/2, -y-1/2, z-1/2'
'-x, y-1/2, z-1/2'

_cell_length_a                   6.4553(14)
_cell_length_b                   15.350(3)
_cell_length_c                   15.588(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1544.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    2106
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      30.42
_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    2.674
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5010
_exptl_absorpt_correction_T_max  0.8779
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90
_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 APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            8721
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         27.00
_reflns_number_total             1684
_reflns_number_gt                1261
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_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)+(0.0418P)²+0.5869P] 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         1684
_refine_ls_number_parameters     108
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0791
_refine_ls_wR_factor_gt          0.0700
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.2442(3) 0.07712(13) 0.50437(13) 0.0091(4) Uani 1 1 d . . .
C2 C 0.2394(3) 0.15034(14) 0.45383(13) 0.0107(4) Uani 1 1 d . . .
H2 H 0.2379 0.1458 0.3931 0.013 Uiso 1 1 calc R . .
C3 C 0.2369(3) 0.23091(13) 0.49367(15) 0.0109(4) Uani 1 1 d . . .
C4 C 0.2428(3) 0.23733(13) 0.58475(14) 0.0121(4) Uani 1 1 d . . .
H4 H 0.2431 0.2929 0.6115 0.014 Uiso 1 1 calc R . .
C5 C 0.2480(3) 0.16384(14) 0.63355(13) 0.0109(4) Uani 1 1 d . . .
H5 H 0.2538 0.1689 0.6942 0.013 Uiso 1 1 calc R . .
C6 C 0.2449(3) 0.07941(14) 0.59555(13) 0.0099(4) Uani 1 1 d . . .
C7 C 0.2500 0.0000 0.64175(18) 0.0094(6) Uani 1 2 d S . .
C8 C 0.2500 0.0000 0.73638(18) 0.0120(6) Uani 1 2 d S . .
C9 C 0.4153(3) -0.03653(16) 0.78158(14) 0.0171(5) Uani 1 1 d . . .
H9 H 0.5280 -0.0618 0.7513 0.020 Uiso 1 1 calc R . .
C10 C 0.4155(4) -0.03601(16) 0.87074(14) 0.0236(5) Uani 1 1 d . . .
H10 H 0.5291 -0.0603 0.9012 0.028 Uiso 1 1 calc R . .
C11 C 0.2500 0.0000 0.9154(2) 0.0238(8) Uani 1 2 d S . .
H11 H 0.2500 0.0000 0.9763 0.029 Uiso 1 2 calc SR . .
Br1 Br 0.23130(5) 0.2500 0.2500 0.02026(13) Uani 1 2 d S . .
O1 O 0.2500 0.0000 0.46142(12) 0.0099(4) Uani 1 2 d S . .
O2 O 0.2312(2) 0.30556(10) 0.44928(10) 0.0152(3) Uani 1 1 d . . .
H2A H 0.2258 0.2945 0.3966 0.023 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
C1 O1 1.361(2) . ?
C1 C2 1.373(3) . ?
C1 C6 1.422(3) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 O2 1.339(2) . ?
C3 C4 1.424(3) . ?
C4 C5 1.361(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.425(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.416(2) . ?
C7 C6 1.416(3) 2 ?
C7 C8 1.475(4) . ?
C8 C9 1.396(3) . ?
C8 C9 1.396(3) 2 ?
C9 C10 1.390(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(3) . ?
C10 H10 0.9500 . ?
C11 C10 1.390(3) 2 ?
C11 H11 0.9500 . ?
O1 C1 1.361(2) 2 ?
O2 H2A 0.8400 . ?

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
O1 C1 C2 115.51(17) . . ?
O1 C1 C6 120.88(18) . . ?
C2 C1 C6 123.61(19) . . ?
C1 C2 C3 118.32(18) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
O2 C3 C2 122.2(2) . . ?
O2 C3 C4 117.18(19) . . ?
C2 C3 C4 120.60(19) . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 121.41(19) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C1 119.2(2) . . ?
C7 C6 C5 124.83(19) . . ?
C1 C6 C5 115.97(18) . . ?
C6 C7 C6 118.9(3) . 2 ?
C6 C7 C8 120.57(13) . . ?
C6 C7 C8 120.57(13) 2 . ?
C9 C8 C9 119.4(3) . 2 ?
C9 C8 C7 120.31(14) . . ?
C9 C8 C7 120.31(14) 2 . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.2(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C10 119.9(3) 2 . ?
C10 C11 H11 120.1 2 . ?
C10 C11 H11 120.1 . . ?
C1 O1 C1 121.0(2) . 2 ?
C3 O2 H2A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -178.93(14) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C1 C2 C3 O2 -179.65(17) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
O2 C3 C4 C5 179.74(16) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
O1 C1 C6 C7 -0.5(3) . . . . ?
C2 C1 C6 C7 180.00(15) . . . . ?
O1 C1 C6 C5 177.25(14) . . . . ?
C2 C1 C6 C5 -2.2(3) . . . . ?
C4 C5 C6 C7 179.96(15) . . . . ?
C4 C5 C6 C1 2.3(3) . . . . ?
C1 C6 C7 C6 0.25(12) . . . 2 ?
C5 C6 C7 C6 -177.3(2) . . . 2 ?
C1 C6 C7 C8 -179.75(12) . . . . ?
C5 C6 C7 C8 2.7(2) . . . . ?
C6 C7 C8 C9 -119.27(14) . . . . ?
C6 C7 C8 C9 60.73(14) 2 . . . ?
C6 C7 C8 C9 60.73(14) . . . 2 ?
C6 C7 C8 C9 -119.27(14) 2 . . 2 ?
C9 C8 C9 C10 -0.37(18) 2 . . . ?
C7 C8 C9 C10 179.63(18) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C9 C10 C11 C10 -0.37(18) . . . 2 ?
C2 C1 O1 C1 179.78(18) . . . 2 ?
C6 C1 O1 C1 0.26(13) . . . 2 ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.072
####################################################################### 
# 
# 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_51119KS
_database_code_depnum_ccdc_archive 'CCDC 1445576'
_audit_update_record             
;
2016-01-06 deposited with the CCDC.
2016-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
13-(2,6-difluorophenyl)-9-methoxy-3H-dibenzo[b,i]xanthen-3-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H16 F2 O3, C H2 Cl2'
_chemical_formula_sum            'C29 H18 Cl2 F2 O3'
_chemical_formula_weight         523.33

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -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                   22.6443(6)
_cell_length_b                   6.8474(2)
_cell_length_c                   30.7630(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.073(7)
_cell_angle_gamma                90
_cell_volume                     4696.4(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    16915
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      25.35

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_F_000             2144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.324
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            30130
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         3.218
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4110
_reflns_number_gt                2908
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0943P)²+5.5491P] 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         4110
_refine_ls_number_parameters     348
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1747
_refine_ls_wR_factor_gt          0.1588
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
C1 C 0.40259(12) 0.6901(4) 0.45589(8) 0.0251(6) Uani 1 1 d . . . . .
H1 H 0.3763 0.6910 0.4768 0.030 Uiso 1 1 calc R U . . .
C2 C 0.46172(13) 0.6931(4) 0.47014(9) 0.0277(6) Uani 1 1 d . . . . .
H2 H 0.4765 0.6991 0.5010 0.033 Uiso 1 1 calc R U . . .
C3 C 0.50423(12) 0.6873(4) 0.43946(9) 0.0280(6) Uani 1 1 d . . . . .
C4 C 0.47939(12) 0.6790(4) 0.39307(8) 0.0275(6) Uani 1 1 d . . . . .
H3 H 0.5059 0.6720 0.3724 0.033 Uiso 1 1 calc R U . . .
C5 C 0.41889(12) 0.6807(4) 0.37784(8) 0.0229(6) Uani 1 1 d . . . . .
C6 C 0.39388(12) 0.6768(4) 0.33175(8) 0.0241(6) Uani 1 1 d . . . . .
H4 H 0.4198 0.6723 0.3106 0.029 Uiso 1 1 calc R U . . .
C7 C 0.33436(12) 0.6794(4) 0.31804(8) 0.0226(6) Uani 1 1 d . . . . .
O1 O 0.31402(8) 0.6759(3) 0.27323(6) 0.0248(4) Uani 1 1 d . . . . .
C8 C 0.25347(12) 0.6780(4) 0.25666(9) 0.0239(6) Uani 1 1 d . . . . .
C9 C 0.23781(12) 0.6768(4) 0.21190(9) 0.0247(6) Uani 1 1 d . . . . .
H5 H 0.2681 0.6733 0.1941 0.030 Uiso 1 1 calc R U . . .
C10 C 0.17680(13) 0.6806(4) 0.19189(9) 0.0260(6) Uani 1 1 d . . . . .
C11 C 0.15923(13) 0.6806(4) 0.14532(9) 0.0292(7) Uani 1 1 d . . . . .
H6 H 0.1887 0.6773 0.1269 0.035 Uiso 1 1 calc R U . . .
C12 C 0.09943(14) 0.6855(4) 0.12700(9) 0.0314(7) Uani 1 1 d . . . . .
C13 C 0.05485(14) 0.6919(4) 0.15410(10) 0.0363(7) Uani 1 1 d . . . . .
H7 H 0.0136 0.6963 0.1411 0.044 Uiso 1 1 calc R U . . .
C14 C 0.07116(13) 0.6919(4) 0.19880(9) 0.0333(7) Uani 1 1 d . . . . .
H8 H 0.0410 0.6956 0.2167 0.040 Uiso 1 1 calc R U . . .
C15 C 0.13237(13) 0.6864(4) 0.21926(9) 0.0286(6) Uani 1 1 d . . . . .
C16 C 0.15051(12) 0.6870(4) 0.26529(9) 0.0299(7) Uani 1 1 d . . . . .
H9 H 0.1208 0.6907 0.2836 0.036 Uiso 1 1 calc R U . . .
C17 C 0.21057(12) 0.6824(4) 0.28492(8) 0.0258(6) Uani 1 1 d . . . . .
C18 C 0.23123(12) 0.6850(4) 0.33221(8) 0.0250(6) Uani 1 1 d . . . . .
C19 C 0.29178(12) 0.6840(4) 0.34809(8) 0.0232(6) Uani 1 1 d . . . . .
C20 C 0.31733(12) 0.6860(4) 0.39433(8) 0.0237(6) Uani 1 1 d . . . . .
H10 H 0.2911 0.6878 0.4153 0.028 Uiso 1 1 calc R U . . .
C21 C 0.37770(12) 0.6855(4) 0.40918(8) 0.0232(6) Uani 1 1 d . . . . .
O2 O 0.55967(9) 0.6873(3) 0.45327(6) 0.0372(5) Uani 1 1 d . . . . .
O3 O 0.07780(9) 0.6870(3) 0.08289(6) 0.0380(5) Uani 1 1 d . . . . .
C22 C 0.12115(14) 0.6861(4) 0.05419(9) 0.0372(7) Uani 1 1 d . . . . .
H11 H 0.1479 0.7989 0.0608 0.056 Uiso 1 1 calc R U . . .
H12 H 0.1005 0.6934 0.0234 0.056 Uiso 1 1 calc R U . . .
H13 H 0.1447 0.5655 0.0586 0.056 Uiso 1 1 calc R U . . .
C23 C 0.18697(12) 0.6877(4) 0.36236(9) 0.0297(7) Uani 1 1 d . . . . .
C24 C 0.17687(16) 0.8492(5) 0.38673(11) 0.0469(9) Uani 1 1 d . . . . .
C25 C 0.13526(17) 0.8564(7) 0.41466(12) 0.0644(12) Uani 1 1 d . . . . .
H14 H 0.1294 0.9719 0.4305 0.077 Uiso 1 1 calc R U . . .
C26 C 0.10253(15) 0.6897(8) 0.41871(11) 0.0728(15) Uani 1 1 d . . . . .
H15 H 0.0739 0.6899 0.4379 0.087 Uiso 1 1 calc R U . . .
C27 C 0.11048(15) 0.5248(7) 0.39575(12) 0.0648(12) Uani 1 1 d . . . . .
H16 H 0.0880 0.4101 0.3989 0.078 Uiso 1 1 calc R U . . .
C28 C 0.15181(14) 0.5279(5) 0.36781(10) 0.0436(8) Uani 1 1 d . . . . .
F1 F 0.21101(11) 1.0105(3) 0.38344(7) 0.0665(7) Uani 1 1 d . . . . .
F2 F 0.15858(9) 0.3654(3) 0.34395(7) 0.0582(6) Uani 1 1 d . . . . .
Cl2 Cl 0.47266(10) 0.7812(3) 0.23052(6) 0.0495(5) Uani 0.5 1 d . . P A -1
C29 C 0.5425(11) 0.783(4) 0.2760(9) 0.227(14) Uiso 0.5 1 d . . P A -1
H17 H 0.5768 0.8380 0.2642 0.272 Uiso 0.5 1 calc R U P A -1
H18 H 0.5351 0.8660 0.3008 0.272 Uiso 0.5 1 calc R U P A -1
Cl1 Cl 0.55909(9) 0.5552(3) 0.29434(7) 0.0581(5) Uani 0.5 1 d . . P A -1
Cl3 Cl 0.23631(13) 0.4959(4) -0.00671(9) 0.0546(7) Uani 0.5 1 d . . P B -2
C30 C 0.2115(3) 0.7297(11) -0.0275(3) 0.0550(19) Uani 0.5 1 d . . P B -2
H19 H 0.2195 0.7441 -0.0579 0.066 Uiso 0.5 1 calc R U P B -2
H20 H 0.1676 0.7402 -0.0286 0.066 Uiso 0.5 1 calc R U P B -2
Cl4 Cl 0.24724(15) 0.9168(5) 0.00526(13) 0.0742(10) Uani 0.5 1 d . . P 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 1.334(4) . ?
C1 C21 1.449(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.462(4) . ?
C2 H2 0.9500 . ?
C3 O2 1.253(3) . ?
C3 C4 1.441(4) . ?
C4 C5 1.368(4) . ?
C4 H3 0.9500 . ?
C5 C6 1.432(4) . ?
C5 C21 1.454(4) . ?
C6 C7 1.340(4) . ?
C6 H4 0.9500 . ?
C7 O1 1.375(3) . ?
C7 C19 1.448(4) . ?
O1 C8 1.377(3) . ?
C8 C9 1.361(4) . ?
C8 C17 1.413(4) . ?
C9 C10 1.411(4) . ?
C9 H5 0.9500 . ?
C10 C11 1.418(4) . ?
C10 C15 1.421(4) . ?
C11 C12 1.373(4) . ?
C11 H6 0.9500 . ?
C12 O3 1.360(3) . ?
C12 C13 1.418(4) . ?
C13 C14 1.360(4) . ?
C13 H7 0.9500 . ?
C14 C15 1.419(4) . ?
C14 H8 0.9500 . ?
C15 C16 1.404(4) . ?
C16 C17 1.388(4) . ?
C16 H9 0.9500 . ?
C17 C18 1.448(4) . ?
C18 C19 1.373(4) . ?
C18 C23 1.480(4) . ?
C19 C20 1.439(4) . ?
C20 C21 1.364(4) . ?
C20 H10 0.9500 . ?
O3 C22 1.431(4) . ?
C22 H11 0.9800 . ?
C22 H12 0.9800 . ?
C22 H13 0.9800 . ?
C23 C24 1.377(4) . ?
C23 C28 1.381(4) . ?
C24 F1 1.362(4) . ?
C24 C25 1.382(5) . ?
C25 C26 1.379(7) . ?
C25 H14 0.9500 . ?
C26 C27 1.360(6) . ?
C26 H15 0.9500 . ?
C27 C28 1.377(5) . ?
C27 H16 0.9500 . ?
C28 F2 1.356(4) . ?
Cl2 C29 1.92(2) . ?
C29 Cl1 1.68(3) . ?
C29 H17 0.9900 . ?
C29 H18 0.9900 . ?
Cl3 C30 1.778(8) . ?
C30 Cl4 1.739(8) . ?
C30 H19 0.9900 . ?
C30 H20 0.9900 . ?

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 C21 121.3(2) . . ?
C2 C1 H1 119.3 . . ?
C21 C1 H1 119.3 . . ?
C1 C2 C3 121.6(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
O2 C3 C4 122.0(2) . . ?
O2 C3 C2 121.0(2) . . ?
C4 C3 C2 117.0(2) . . ?
C5 C4 C3 122.2(2) . . ?
C5 C4 H3 118.9 . . ?
C3 C4 H3 118.9 . . ?
C4 C5 C6 122.5(2) . . ?
C4 C5 C21 119.6(2) . . ?
C6 C5 C21 117.9(2) . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 H4 119.6 . . ?
C5 C6 H4 119.6 . . ?
C6 C7 O1 117.2(2) . . ?
C6 C7 C19 123.0(2) . . ?
O1 C7 C19 119.8(2) . . ?
C7 O1 C8 120.5(2) . . ?
C9 C8 O1 116.2(2) . . ?
C9 C8 C17 122.5(3) . . ?
O1 C8 C17 121.3(2) . . ?
C8 C9 C10 120.2(2) . . ?
C8 C9 H5 119.9 . . ?
C10 C9 H5 119.9 . . ?
C9 C10 C11 121.4(3) . . ?
C9 C10 C15 118.9(2) . . ?
C11 C10 C15 119.7(3) . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H6 120.1 . . ?
C10 C11 H6 120.1 . . ?
O3 C12 C11 124.5(3) . . ?
O3 C12 C13 114.7(3) . . ?
C11 C12 C13 120.8(3) . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H7 120.0 . . ?
C12 C13 H7 120.0 . . ?
C13 C14 C15 121.3(3) . . ?
C13 C14 H8 119.3 . . ?
C15 C14 H8 119.3 . . ?
C16 C15 C14 122.6(3) . . ?
C16 C15 C10 119.0(3) . . ?
C14 C15 C10 118.4(2) . . ?
C17 C16 C15 122.0(3) . . ?
C17 C16 H9 119.0 . . ?
C15 C16 H9 119.0 . . ?
C16 C17 C8 117.4(2) . . ?
C16 C17 C18 123.8(2) . . ?
C8 C17 C18 118.8(2) . . ?
C19 C18 C17 119.0(2) . . ?
C19 C18 C23 121.4(2) . . ?
C17 C18 C23 119.6(2) . . ?
C18 C19 C20 123.8(2) . . ?
C18 C19 C7 120.5(2) . . ?
C20 C19 C7 115.7(2) . . ?
C21 C20 C19 122.5(2) . . ?
C21 C20 H10 118.8 . . ?
C19 C20 H10 118.8 . . ?
C20 C21 C1 121.7(2) . . ?
C20 C21 C5 120.0(2) . . ?
C1 C21 C5 118.3(2) . . ?
C12 O3 C22 116.7(2) . . ?
O3 C22 H11 109.5 . . ?
O3 C22 H12 109.5 . . ?
H11 C22 H12 109.5 . . ?
O3 C22 H13 109.5 . . ?
H11 C22 H13 109.5 . . ?
H12 C22 H13 109.5 . . ?
C24 C23 C28 114.6(3) . . ?
C24 C23 C18 123.1(3) . . ?
C28 C23 C18 122.3(3) . . ?
F1 C24 C23 117.4(3) . . ?
F1 C24 C25 118.4(3) . . ?
C23 C24 C25 124.2(4) . . ?
C26 C25 C24 117.5(4) . . ?
C26 C25 H14 121.2 . . ?
C24 C25 H14 121.2 . . ?
C27 C26 C25 121.2(3) . . ?
C27 C26 H15 119.4 . . ?
C25 C26 H15 119.4 . . ?
C26 C27 C28 118.5(4) . . ?
C26 C27 H16 120.7 . . ?
C28 C27 H16 120.7 . . ?
F2 C28 C27 118.6(3) . . ?
F2 C28 C23 117.5(3) . . ?
C27 C28 C23 123.8(4) . . ?
Cl1 C29 Cl2 110.4(15) . . ?
Cl1 C29 H17 109.6 . . ?
Cl2 C29 H17 109.6 . . ?
Cl1 C29 H18 109.6 . . ?
Cl2 C29 H18 109.6 . . ?
H17 C29 H18 108.1 . . ?
Cl4 C30 Cl3 111.7(5) . . ?
Cl4 C30 H19 109.3 . . ?
Cl3 C30 H19 109.3 . . ?
Cl4 C30 H20 109.3 . . ?
Cl3 C30 H20 109.3 . . ?
H19 C30 H20 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 C1 C2 C3 -1.4(4) . . . . ?
C1 C2 C3 O2 -179.0(3) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
O2 C3 C4 C5 -179.4(3) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
C3 C4 C5 C6 178.6(3) . . . . ?
C3 C4 C5 C21 -1.8(4) . . . . ?
C4 C5 C6 C7 -179.8(3) . . . . ?
C21 C5 C6 C7 0.6(4) . . . . ?
C5 C6 C7 O1 179.8(2) . . . . ?
C5 C6 C7 C19 -0.7(4) . . . . ?
C6 C7 O1 C8 179.9(2) . . . . ?
C19 C7 O1 C8 0.4(3) . . . . ?
C7 O1 C8 C9 179.2(2) . . . . ?
C7 O1 C8 C17 -0.4(3) . . . . ?
O1 C8 C9 C10 -179.4(2) . . . . ?
C17 C8 C9 C10 0.2(4) . . . . ?
C8 C9 C10 C11 179.6(2) . . . . ?
C8 C9 C10 C15 0.2(4) . . . . ?
C9 C10 C11 C12 -179.7(2) . . . . ?
C15 C10 C11 C12 -0.3(4) . . . . ?
C10 C11 C12 O3 179.6(2) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?
O3 C12 C13 C14 -179.7(3) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
C13 C14 C15 C16 179.8(3) . . . . ?
C13 C14 C15 C10 -0.1(4) . . . . ?
C9 C10 C15 C16 -0.4(4) . . . . ?
C11 C10 C15 C16 -179.8(2) . . . . ?
C9 C10 C15 C14 179.5(2) . . . . ?
C11 C10 C15 C14 0.1(4) . . . . ?
C14 C15 C16 C17 -179.7(3) . . . . ?
C10 C15 C16 C17 0.1(4) . . . . ?
C15 C16 C17 C8 0.3(4) . . . . ?
C15 C16 C17 C18 179.3(3) . . . . ?
C9 C8 C17 C16 -0.5(4) . . . . ?
O1 C8 C17 C16 179.1(2) . . . . ?
C9 C8 C17 C18 -179.5(2) . . . . ?
O1 C8 C17 C18 0.1(4) . . . . ?
C16 C17 C18 C19 -178.7(3) . . . . ?
C8 C17 C18 C19 0.3(4) . . . . ?
C16 C17 C18 C23 1.6(4) . . . . ?
C8 C17 C18 C23 -179.4(2) . . . . ?
C17 C18 C19 C20 -179.9(2) . . . . ?
C23 C18 C19 C20 -0.2(4) . . . . ?
C17 C18 C19 C7 -0.3(4) . . . . ?
C23 C18 C19 C7 179.4(2) . . . . ?
C6 C7 C19 C18 -179.5(3) . . . . ?
O1 C7 C19 C18 0.0(4) . . . . ?
C6 C7 C19 C20 0.1(4) . . . . ?
O1 C7 C19 C20 179.6(2) . . . . ?
C18 C19 C20 C21 -179.8(3) . . . . ?
C7 C19 C20 C21 0.6(4) . . . . ?
C19 C20 C21 C1 179.2(2) . . . . ?
C19 C20 C21 C5 -0.6(4) . . . . ?
C2 C1 C21 C20 -178.8(3) . . . . ?
C2 C1 C21 C5 1.1(4) . . . . ?
C4 C5 C21 C20 -179.6(2) . . . . ?
C6 C5 C21 C20 0.0(4) . . . . ?
C4 C5 C21 C1 0.6(4) . . . . ?
C6 C5 C21 C1 -179.8(2) . . . . ?
C11 C12 O3 C22 -0.9(4) . . . . ?
C13 C12 O3 C22 178.3(2) . . . . ?
C19 C18 C23 C24 71.8(4) . . . . ?
C17 C18 C23 C24 -108.5(3) . . . . ?
C19 C18 C23 C28 -109.1(3) . . . . ?
C17 C18 C23 C28 70.6(4) . . . . ?
C28 C23 C24 F1 178.7(3) . . . . ?
C18 C23 C24 F1 -2.0(5) . . . . ?
C28 C23 C24 C25 -0.1(5) . . . . ?
C18 C23 C24 C25 179.1(3) . . . . ?
F1 C24 C25 C26 -177.9(3) . . . . ?
C23 C24 C25 C26 1.0(6) . . . . ?
C24 C25 C26 C27 -0.6(6) . . . . ?
C25 C26 C27 C28 -0.6(6) . . . . ?
C26 C27 C28 F2 -178.2(3) . . . . ?
C26 C27 C28 C23 1.6(6) . . . . ?
C24 C23 C28 F2 178.5(3) . . . . ?
C18 C23 C28 F2 -0.7(4) . . . . ?
C24 C23 C28 C27 -1.2(5) . . . . ?
C18 C23 C28 C27 179.6(3) . . . . ?

_refine_diff_density_max         0.551
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.061

