# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_yxj2014004a
_database_code_depnum_ccdc_archive 'CCDC 1062626'
_audit_update_record             
;
2015-04-30 deposited with the CCDC.
2015-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
"4,8-bis(4-yl-triphenylphosphine oxide)-2,6-dimethylbenzo[1,2-d:4,5-d']bis(oxazole)"
_chemical_name_common            TPO-DBBO
_chemical_melting_point          403
_chemical_formula_moiety         804.78
_chemical_formula_sum            'C48 H42 N2 O6 P2'
_chemical_formula_weight         804.78

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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                   9.8428(15)
_cell_length_b                   17.450(3)
_cell_length_c                   12.4113(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.866(2)
_cell_angle_gamma                90.00
_cell_volume                     2086.2(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(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          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             844
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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            11642
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3597
_reflns_number_gt                3094
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.1665P)²+0.3913P] 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_number_reflns         3597
_refine_ls_number_parameters     279
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0624
_refine_ls_wR_factor_ref         0.2190
_refine_ls_wR_factor_gt          0.2009
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.092
_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
P1 P 0.33389(6) 0.17269(3) 0.68002(5) 0.0411(3) Uani 1 1 d . . .
O2 O 1.02905(16) 0.14471(9) 0.93266(13) 0.0429(4) Uani 1 1 d . . .
C16 C 0.7408(2) 0.07104(12) 0.87602(17) 0.0371(5) Uani 1 1 d . . .
C19 C 0.8703(2) 0.03552(13) 0.93817(17) 0.0369(5) Uani 1 1 d . . .
C21 C 0.9988(2) 0.07036(12) 0.95930(17) 0.0363(5) Uani 1 1 d . . .
N1 N 0.77222(19) -0.09341(11) 0.97316(16) 0.0411(5) Uani 1 1 d . . .
C20 C 0.8768(2) -0.03852(13) 0.98195(17) 0.0363(5) Uani 1 1 d . . .
C13 C 0.4966(2) 0.13654(12) 0.75764(18) 0.0381(5) Uani 1 1 d . . .
C15 C 0.7427(2) 0.11488(13) 0.78291(19) 0.0405(5) Uani 1 1 d . . .
H15 H 0.8261 0.1230 0.7605 0.049 Uiso 1 1 calc R . .
C14 C 0.6222(2) 0.14629(13) 0.72377(19) 0.0429(5) Uani 1 1 d . . .
H14 H 0.6243 0.1744 0.6604 0.052 Uiso 1 1 calc R . .
C1 C 0.3386(2) 0.15085(14) 0.5392(2) 0.0457(6) Uani 1 1 d . . .
C18 C 0.4948(2) 0.09375(14) 0.8517(2) 0.0443(6) Uani 1 1 d . . .
H18 H 0.4122 0.0873 0.8759 0.053 Uiso 1 1 calc R . .
O1 O 0.21536(17) 0.13653(11) 0.71819(16) 0.0553(5) Uani 1 1 d . . .
C7 C 0.3312(3) 0.27560(13) 0.69333(19) 0.0451(6) Uani 1 1 d . . .
C17 C 0.6158(2) 0.06078(14) 0.90952(19) 0.0433(6) Uani 1 1 d . . .
H17 H 0.6134 0.0314 0.9716 0.052 Uiso 1 1 calc R . .
C22 C 1.1665(2) 0.15318(14) 0.97635(19) 0.0429(5) Uani 1 1 d . . .
C23 C 1.2292(3) 0.22875(15) 0.9638(2) 0.0587(7) Uani 1 1 d . . .
H23A H 1.3278 0.2232 0.9720 0.088 Uiso 1 1 calc R . .
H23B H 1.2097 0.2631 1.0191 0.088 Uiso 1 1 calc R . .
H23C H 1.1907 0.2490 0.8921 0.088 Uiso 1 1 calc R . .
C2 C 0.3412(3) 0.20526(17) 0.4596(2) 0.0599(7) Uani 1 1 d . . .
H2 H 0.3393 0.2570 0.4773 0.072 Uiso 1 1 calc R . .
C8 C 0.4516(3) 0.32016(15) 0.7191(3) 0.0590(7) Uani 1 1 d . . .
H8 H 0.5383 0.2970 0.7279 0.071 Uiso 1 1 calc R . .
C12 C 0.2035(3) 0.31146(17) 0.6787(3) 0.0655(8) Uani 1 1 d . . .
H12 H 0.1224 0.2829 0.6592 0.079 Uiso 1 1 calc R . .
C10 C 0.3126(5) 0.43361(17) 0.7182(3) 0.0756(10) Uani 1 1 d . . .
H10 H 0.3058 0.4864 0.7264 0.091 Uiso 1 1 calc R . .
C4 C 0.3468(4) 0.1084(2) 0.3254(3) 0.0822(11) Uani 1 1 d . . .
H4 H 0.3476 0.0942 0.2533 0.099 Uiso 1 1 calc R . .
C11 C 0.1963(4) 0.3903(2) 0.6932(3) 0.0799(10) Uani 1 1 d . . .
H11 H 0.1100 0.4137 0.6855 0.096 Uiso 1 1 calc R . .
C9 C 0.4420(4) 0.39914(17) 0.7315(3) 0.0721(9) Uani 1 1 d . . .
H9 H 0.5221 0.4287 0.7488 0.086 Uiso 1 1 calc R . .
C3 C 0.3468(4) 0.1835(2) 0.3533(3) 0.0746(9) Uani 1 1 d . . .
H3A H 0.3505 0.2208 0.3005 0.090 Uiso 1 1 calc R . .
C5 C 0.3455(6) 0.0544(2) 0.4034(4) 0.1101(17) Uani 1 1 d . . .
H5 H 0.3502 0.0030 0.3851 0.132 Uiso 1 1 calc R . .
C6 C 0.3374(5) 0.07443(19) 0.5101(3) 0.0890(13) Uani 1 1 d . . .
H6 H 0.3311 0.0366 0.5616 0.107 Uiso 1 1 calc R . .
O3 O 0.9462(3) 0.1496(2) 0.6164(2) 0.0970(9) Uani 1 1 d D . .
C24A C 0.9297(6) 0.1039(4) 0.5239(6) 0.122(3) Uani 0.877(12) 1 d PD A 1
H24A H 0.9695 0.1290 0.4689 0.183 Uiso 0.877(12) 1 calc PR A 1
H24B H 0.8326 0.0952 0.4957 0.183 Uiso 0.877(12) 1 calc PR A 1
H24C H 0.9755 0.0557 0.5428 0.183 Uiso 0.877(12) 1 calc PR A 1
C24B C 0.962(3) 0.0705(10) 0.621(3) 0.083(13) Uani 0.123(12) 1 d PD A 2
H24D H 1.0252 0.0551 0.5757 0.124 Uiso 0.123(12) 1 calc PR A 2
H24E H 0.8735 0.0465 0.5952 0.124 Uiso 0.123(12) 1 calc PR A 2
H24F H 0.9982 0.0552 0.6959 0.124 Uiso 0.123(12) 1 calc PR A 2
H3 H 1.026(3) 0.141(3) 0.656(4) 0.117(17) Uiso 1 1 d 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
P1 O1 1.4869(19) . ?
P1 C1 1.799(3) . ?
P1 C7 1.804(2) . ?
P1 C13 1.804(2) . ?
O2 C22 1.358(3) . ?
O2 C21 1.386(3) . ?
C16 C17 1.389(3) . ?
C16 C15 1.389(3) . ?
C16 C19 1.483(3) . ?
C19 C21 1.380(3) . ?
C19 C20 1.398(3) . ?
C21 C20 1.404(3) 3_757 ?
N1 C22 1.299(3) 3_757 ?
N1 C20 1.394(3) . ?
C20 C21 1.404(3) 3_757 ?
C13 C18 1.389(3) . ?
C13 C14 1.396(3) . ?
C15 C14 1.375(3) . ?
C1 C2 1.374(4) . ?
C1 C6 1.381(4) . ?
C18 C17 1.382(3) . ?
C7 C12 1.382(4) . ?
C7 C8 1.399(4) . ?
C22 N1 1.299(3) 3_757 ?
C22 C23 1.477(3) . ?
C2 C3 1.384(4) . ?
C8 C9 1.392(4) . ?
C12 C11 1.392(4) . ?
C10 C11 1.353(6) . ?
C10 C9 1.388(5) . ?
C4 C5 1.352(6) . ?
C4 C3 1.355(5) . ?
C5 C6 1.388(6) . ?
O3 C24A 1.379(6) . ?
O3 C24B 1.389(18) . ?

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 P1 C1 113.47(12) . . ?
O1 P1 C7 111.46(12) . . ?
C1 P1 C7 107.68(11) . . ?
O1 P1 C13 110.48(10) . . ?
C1 P1 C13 104.32(11) . . ?
C7 P1 C13 109.11(11) . . ?
C22 O2 C21 104.57(17) . . ?
C17 C16 C15 119.0(2) . . ?
C17 C16 C19 120.66(19) . . ?
C15 C16 C19 120.3(2) . . ?
C21 C19 C20 111.5(2) . . ?
C21 C19 C16 124.8(2) . . ?
C20 C19 C16 123.7(2) . . ?
C19 C21 O2 126.91(19) . . ?
C19 C21 C20 126.3(2) . 3_757 ?
O2 C21 C20 106.70(18) . 3_757 ?
C22 N1 C20 104.60(19) 3_757 . ?
N1 C20 C19 129.1(2) . . ?
N1 C20 C21 108.64(19) . 3_757 ?
C19 C20 C21 122.2(2) . 3_757 ?
C18 C13 C14 118.9(2) . . ?
C18 C13 P1 118.28(17) . . ?
C14 C13 P1 122.70(17) . . ?
C14 C15 C16 120.4(2) . . ?
C15 C14 C13 120.8(2) . . ?
C2 C1 C6 118.7(3) . . ?
C2 C1 P1 124.1(2) . . ?
C6 C1 P1 117.3(2) . . ?
C17 C18 C13 120.1(2) . . ?
C12 C7 C8 118.9(2) . . ?
C12 C7 P1 118.0(2) . . ?
C8 C7 P1 123.12(19) . . ?
C18 C17 C16 120.8(2) . . ?
N1 C22 O2 115.5(2) 3_757 . ?
N1 C22 C23 127.2(2) 3_757 . ?
O2 C22 C23 117.3(2) . . ?
C1 C2 C3 120.4(3) . . ?
C9 C8 C7 120.1(3) . . ?
C7 C12 C11 120.0(3) . . ?
C11 C10 C9 119.9(3) . . ?
C5 C4 C3 119.3(3) . . ?
C10 C11 C12 121.2(3) . . ?
C10 C9 C8 119.8(3) . . ?
C4 C3 C2 120.7(3) . . ?
C4 C5 C6 121.2(3) . . ?
C1 C6 C5 119.5(4) . . ?
C24A O3 C24B 56.9(16) . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.080
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_preparation       Luminescent
