# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_qq
_database_code_depnum_ccdc_archive 'CCDC 1025707'
_audit_update_record             
;
2014-09-23 deposited with the CCDC.
2015-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
14-(4-methylphenyl)-7,14-dihydro-dibenzo[a,j]xanthene
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H20 O'
_chemical_formula_weight         372.44

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           Orthorhombic
_symmetry_space_group_name_H-M   'Pna2(1) '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   14.015(4)
_cell_length_b                   17.350(6)
_cell_length_c                   7.950(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1933.2(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            White
_exptl_crystal_size_max          .32
_exptl_crystal_size_mid          .24
_exptl_crystal_size_min          .12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9212
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_sigmaI/netI    0.0840
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         27.44
_reflns_number_total             4050
_reflns_number_gt                2410
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0500P)²+0.0104P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_number_reflns         4050
_refine_ls_number_parameters     267
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1146
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1422
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
C20 C 0.90228(18) 0.59685(17) 0.3255(3) 0.0458(7) Uani 1 1 d . . .
C15 C 0.9405(3) 0.8064(2) 0.4155(4) 0.0736(10) Uani 1 1 d . . .
H15 H 0.9892 0.8427 0.4079 0.088 Uiso 1 1 calc R . .
C5 C 0.7985(4) 0.2532(2) 0.4234(5) 0.0852(12) Uani 1 1 d . . .
H5 H 0.8257 0.2044 0.4192 0.102 Uiso 1 1 calc R . .
C10 C 0.8672(2) 0.45661(17) 0.3294(3) 0.0503(8) Uani 1 1 d . . .
C3 C 0.9488(3) 0.3100(2) 0.3140(4) 0.0807(12) Uani 1 1 d . . .
H3 H 0.9763 0.2613 0.3079 0.097 Uiso 1 1 calc R . .
C23 C 0.79617(19) 0.53285(17) 0.0097(4) 0.0511(8) Uani 1 1 d . . .
H23 H 0.8606 0.5216 -0.0035 0.061 Uiso 1 1 calc R . .
C19 C 0.88467(18) 0.67470(17) 0.3762(3) 0.0480(7) Uani 1 1 d . . .
C21 C 0.8246(2) 0.53652(16) 0.3264(4) 0.0466(7) Uani 1 1 d . . .
C11 C 0.9925(2) 0.5785(2) 0.2760(4) 0.0547(8) Uani 1 1 d . . .
C6 C 0.7076(4) 0.2609(2) 0.4796(5) 0.0924(13) Uani 1 1 d . . .
H6 H 0.6729 0.2180 0.5139 0.111 Uiso 1 1 calc R . .
O1 O 1.01842(13) 0.50489(15) 0.2311(3) 0.0663(6) Uani 1 1 d . . .
C2 C 1.0010(3) 0.3723(2) 0.2680(5) 0.0728(10) Uani 1 1 d . . .
H2 H 1.0634 0.3666 0.2299 0.087 Uiso 1 1 calc R . .
C17 C 0.7821(3) 0.7744(2) 0.4904(4) 0.0673(10) Uani 1 1 d . . .
H17 H 0.7236 0.7890 0.5355 0.081 Uiso 1 1 calc R . .
C25 C 0.6433(2) 0.55286(17) -0.1165(4) 0.0548(8) Uani 1 1 d . . .
C24 C 0.7390(2) 0.53749(18) -0.1305(4) 0.0563(8) Uani 1 1 d . . .
H24 H 0.7656 0.5301 -0.2365 0.068 Uiso 1 1 calc R . .
C7 C 0.6675(3) 0.3332(2) 0.4848(4) 0.0793(11) Uani 1 1 d . . .
H7 H 0.6052 0.3389 0.5234 0.095 Uiso 1 1 calc R . .
C18 C 0.7957(2) 0.69989(18) 0.4387(3) 0.0536(8) Uani 1 1 d . . .
H18 H 0.7453 0.6652 0.4450 0.064 Uiso 1 1 calc R . .
C9 C 0.8123(2) 0.39158(16) 0.3782(4) 0.0540(8) Uani 1 1 d . . .
C13 C 1.0485(2) 0.7077(3) 0.3044(4) 0.0728(10) Uani 1 1 d . . .
H13 H 1.0968 0.7440 0.2937 0.087 Uiso 1 1 calc R . .
C12 C 1.0658(2) 0.6336(3) 0.2628(4) 0.0693(10) Uani 1 1 d . . .
H12 H 1.1260 0.6190 0.2256 0.083 Uiso 1 1 calc R . .
C22 C 0.76023(17) 0.54461(15) 0.1711(3) 0.0406(6) Uani 1 1 d . . .
C14 C 0.9587(2) 0.73067(19) 0.3633(4) 0.0576(8) Uani 1 1 d . . .
C8 C 0.7171(2) 0.39648(18) 0.4346(4) 0.0607(8) Uani 1 1 d . . .
H8 H 0.6873 0.4444 0.4375 0.073 Uiso 1 1 calc R . .
C1 C 0.9591(2) 0.44519(19) 0.2790(4) 0.0581(8) Uani 1 1 d . . .
C16 C 0.8553(3) 0.8287(2) 0.4761(5) 0.0758(10) Uani 1 1 d . . .
H16 H 0.8452 0.8796 0.5081 0.091 Uiso 1 1 calc R . .
C27 C 0.66389(19) 0.56051(16) 0.1848(4) 0.0534(8) Uani 1 1 d . . .
H27 H 0.6370 0.5686 0.2903 0.064 Uiso 1 1 calc R . .
C4 C 0.8530(3) 0.31715(19) 0.3714(4) 0.0692(9) Uani 1 1 d . . .
C26 C 0.60713(19) 0.56454(18) 0.0420(4) 0.0563(9) Uani 1 1 d . . .
H26 H 0.5425 0.5755 0.0540 0.068 Uiso 1 1 calc R . .
C28 C 0.5812(2) 0.5600(2) -0.2732(5) 0.0885(12) Uani 1 1 d . . .
H28A H 0.5152 0.5585 -0.2415 0.133 Uiso 1 1 calc R . .
H28B H 0.5948 0.5181 -0.3483 0.133 Uiso 1 1 calc R . .
H28C H 0.5946 0.6080 -0.3285 0.133 Uiso 1 1 calc R . .
H1A H 0.7847(19) 0.5468(15) 0.429(4) 0.056(8) 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
C20 C11 1.362(4) . ?
C20 C19 1.431(4) . ?
C20 C21 1.511(4) . ?
C15 C16 1.345(5) . ?
C15 C14 1.402(5) . ?
C15 H15 0.9300 . ?
C5 C6 1.357(5) . ?
C5 C4 1.408(5) . ?
C5 H5 0.9300 . ?
C10 C1 1.363(4) . ?
C10 C9 1.419(4) . ?
C10 C21 1.510(4) . ?
C3 C2 1.355(5) . ?
C3 C4 1.424(5) . ?
C3 H3 0.9300 . ?
C23 C24 1.376(4) . ?
C23 C22 1.394(4) . ?
C23 H23 0.9300 . ?
C19 C18 1.412(4) . ?
C19 C14 1.425(4) . ?
C21 C22 1.535(4) . ?
C21 H1A 1.00(3) . ?
C11 O1 1.375(4) . ?
C11 C12 1.406(4) . ?
C6 C7 1.375(5) . ?
C6 H6 0.9300 . ?
O1 C1 1.382(4) . ?
C2 C1 1.397(4) . ?
C2 H2 0.9300 . ?
C17 C18 1.370(4) . ?
C17 C16 1.397(5) . ?
C17 H17 0.9300 . ?
C25 C24 1.371(4) . ?
C25 C26 1.373(4) . ?
C25 C28 1.525(5) . ?
C24 H24 0.9300 . ?
C7 C8 1.359(4) . ?
C7 H7 0.9300 . ?
C18 H18 0.9300 . ?
C9 C8 1.411(4) . ?
C9 C4 1.413(4) . ?
C13 C12 1.350(5) . ?
C13 C14 1.401(4) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C22 C27 1.382(4) . ?
C8 H8 0.9300 . ?
C16 H16 0.9300 . ?
C27 C26 1.388(4) . ?
C27 H27 0.9300 . ?
C26 H26 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 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
C11 C20 C19 117.5(3) . . ?
C11 C20 C21 120.6(3) . . ?
C19 C20 C21 121.9(2) . . ?
C16 C15 C14 122.4(3) . . ?
C16 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C6 C5 C4 121.9(4) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C1 C10 C9 118.5(3) . . ?
C1 C10 C21 120.2(3) . . ?
C9 C10 C21 121.3(3) . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C24 C23 C22 121.8(2) . . ?
C24 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
C18 C19 C14 117.2(3) . . ?
C18 C19 C20 122.9(3) . . ?
C14 C19 C20 119.8(2) . . ?
C10 C21 C20 110.5(2) . . ?
C10 C21 C22 109.2(2) . . ?
C20 C21 C22 110.9(2) . . ?
C10 C21 H1A 111.8(15) . . ?
C20 C21 H1A 106.4(15) . . ?
C22 C21 H1A 108.0(15) . . ?
C20 C11 O1 122.4(3) . . ?
C20 C11 C12 122.8(3) . . ?
O1 C11 C12 114.8(3) . . ?
C5 C6 C7 118.9(4) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C11 O1 C1 117.8(2) . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C24 C25 C26 117.7(3) . . ?
C24 C25 C28 120.5(3) . . ?
C26 C25 C28 121.8(3) . . ?
C25 C24 C23 121.0(3) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C8 C7 C6 121.3(4) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C17 C18 C19 121.4(3) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C8 C9 C4 116.7(3) . . ?
C8 C9 C10 123.5(3) . . ?
C4 C9 C10 119.8(3) . . ?
C12 C13 C14 121.0(3) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C12 C11 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C27 C22 C23 117.0(3) . . ?
C27 C22 C21 121.9(3) . . ?
C23 C22 C21 121.0(2) . . ?
C13 C14 C15 121.9(3) . . ?
C13 C14 C19 119.0(3) . . ?
C15 C14 C19 119.1(3) . . ?
C7 C8 C9 121.9(3) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 H8 119.1 . . ?
C10 C1 O1 122.7(3) . . ?
C10 C1 C2 123.2(3) . . ?
O1 C1 C2 114.1(3) . . ?
C15 C16 C17 119.3(3) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C22 C27 C26 120.4(3) . . ?
C22 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C5 C4 C9 119.3(3) . . ?
C5 C4 C3 122.5(4) . . ?
C9 C4 C3 118.2(3) . . ?
C25 C26 C27 122.1(2) . . ?
C25 C26 H26 118.9 . . ?
C27 C26 H26 118.9 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.050
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethylacetate'
