# 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_zzq-tpshelxl
_database_code_depnum_ccdc_archive 'CCDC 1410444'
_audit_update_record             
;
2015-07-03 deposited with the CCDC.
2015-09-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        TP
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H19 B F2 N2 O'
_chemical_formula_weight         412.23

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   6.5345(13)
_cell_length_b                   13.047(3)
_cell_length_c                   24.300(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.76(3)
_cell_angle_gamma                90.00
_cell_volume                     2061.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    14967
_cell_measurement_theta_min      6.25
_cell_measurement_theta_max      55.05

_exptl_crystal_description       yellow
_exptl_crystal_colour            block
_exptl_crystal_size_max          0.517
_exptl_crystal_size_mid          0.341
_exptl_crystal_size_min          0.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.000
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            18940
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4710
_reflns_number_gt                3485
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  SHELXL-97

_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)+(0.0518P)²+0.5068P] 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         4710
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1204
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_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
B1 B -0.2987(3) -0.01059(14) 0.79567(8) 0.0283(4) Uani 1 1 d . . .
C1 C -0.6561(3) 0.01903(13) 0.74665(7) 0.0322(4) Uani 1 1 d . . .
H1 H -0.6840 -0.0487 0.7553 0.039 Uiso 1 1 calc R . .
C2 C -0.8015(3) 0.07407(14) 0.71526(7) 0.0375(4) Uani 1 1 d . . .
H2 H -0.9270 0.0446 0.7026 0.045 Uiso 1 1 calc R . .
C3 C -0.7586(3) 0.17570(15) 0.70252(8) 0.0386(4) Uani 1 1 d . . .
H3 H -0.8549 0.2144 0.6807 0.046 Uiso 1 1 calc R . .
C4 C -0.5736(3) 0.21817(13) 0.72229(7) 0.0332(4) Uani 1 1 d . . .
H4 H -0.5448 0.2859 0.7140 0.040 Uiso 1 1 calc R . .
C5 C -0.4277(3) 0.15967(12) 0.75495(6) 0.0256(3) Uani 1 1 d . . .
C6 C -0.2332(2) 0.19964(12) 0.77723(6) 0.0256(3) Uani 1 1 d . . .
H6 H -0.1931 0.2640 0.7659 0.031 Uiso 1 1 calc R . .
C7 C -0.1054(2) 0.14695(11) 0.81431(6) 0.0226(3) Uani 1 1 d . . .
C8 C 0.0846(2) 0.18813(11) 0.84324(6) 0.0224(3) Uani 1 1 d . . .
C9 C 0.1225(2) 0.29412(11) 0.84679(6) 0.0232(3) Uani 1 1 d . . .
H9 H 0.0310 0.3391 0.8275 0.028 Uiso 1 1 calc R . .
C10 C 0.2923(2) 0.33274(11) 0.87823(6) 0.0242(3) Uani 1 1 d . . .
H10 H 0.3123 0.4033 0.8804 0.029 Uiso 1 1 calc R . .
C11 C 0.4354(2) 0.26689(11) 0.90708(6) 0.0240(3) Uani 1 1 d . . .
C12 C 0.4019(3) 0.16067(12) 0.90206(6) 0.0268(3) Uani 1 1 d . . .
H12 H 0.4968 0.1153 0.9197 0.032 Uiso 1 1 calc R . .
C13 C 0.2298(2) 0.12317(11) 0.87119(6) 0.0252(3) Uani 1 1 d . . .
H13 H 0.2097 0.0527 0.8689 0.030 Uiso 1 1 calc R . .
C14 C 0.6784(2) 0.40701(11) 0.93433(6) 0.0233(3) Uani 1 1 d . . .
C15 C 0.7118(2) 0.44379(12) 0.88221(7) 0.0271(3) Uani 1 1 d . . .
H15 H 0.6840 0.4024 0.8512 0.032 Uiso 1 1 calc R . .
C16 C 0.7865(3) 0.54213(13) 0.87664(7) 0.0325(4) Uani 1 1 d . . .
H16 H 0.8086 0.5664 0.8417 0.039 Uiso 1 1 calc R . .
C17 C 0.8288(3) 0.60466(13) 0.92229(8) 0.0342(4) Uani 1 1 d . . .
H17 H 0.8786 0.6707 0.9182 0.041 Uiso 1 1 calc R . .
C18 C 0.7963(3) 0.56796(13) 0.97400(7) 0.0326(4) Uani 1 1 d . . .
H18 H 0.8243 0.6096 1.0049 0.039 Uiso 1 1 calc R . .
C19 C 0.7220(2) 0.46936(12) 0.98022(7) 0.0281(3) Uani 1 1 d . . .
H19 H 0.7015 0.4451 1.0152 0.034 Uiso 1 1 calc R . .
C20 C 0.6146(3) 0.21225(13) 1.02850(7) 0.0337(4) Uani 1 1 d . . .
H20 H 0.4821 0.2347 1.0329 0.040 Uiso 1 1 calc R . .
C21 C 0.7186(3) 0.14935(14) 1.06803(7) 0.0397(4) Uani 1 1 d . . .
H21 H 0.6550 0.1293 1.0989 0.048 Uiso 1 1 calc R . .
C22 C 0.9160(3) 0.11631(13) 1.06188(7) 0.0375(4) Uani 1 1 d . . .
H22 H 0.9856 0.0747 1.0886 0.045 Uiso 1 1 calc R . .
C23 C 1.0094(3) 0.14546(13) 1.01581(8) 0.0340(4) Uani 1 1 d . . .
H23 H 1.1417 0.1229 1.0113 0.041 Uiso 1 1 calc R . .
C24 C 0.9063(3) 0.20818(12) 0.97632(7) 0.0281(4) Uani 1 1 d . . .
H24 H 0.9702 0.2280 0.9455 0.034 Uiso 1 1 calc R . .
C25 C 0.7096(2) 0.24150(11) 0.98236(6) 0.0244(3) Uani 1 1 d . . .
F1 F -0.20433(16) -0.06030(7) 0.75385(4) 0.0365(3) Uani 1 1 d . . .
F2 F -0.38723(18) -0.08184(8) 0.82773(4) 0.0448(3) Uani 1 1 d . . .
N1 N -0.4716(2) 0.06003(10) 0.76575(5) 0.0255(3) Uani 1 1 d . . .
N2 N 0.6026(2) 0.30554(10) 0.94082(6) 0.0288(3) Uani 1 1 d . . .
O1 O -0.14963(18) 0.05068(8) 0.82906(4) 0.0282(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
B1 F2 1.377(2) . ?
B1 F1 1.400(2) . ?
B1 O1 1.445(2) . ?
B1 N1 1.578(2) . ?
C1 N1 1.357(2) . ?
C1 C2 1.362(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.397(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.403(2) . ?
C4 H4 0.9300 . ?
C5 N1 1.362(2) . ?
C5 C6 1.429(2) . ?
C6 C7 1.353(2) . ?
C6 H6 0.9300 . ?
C7 O1 1.3455(18) . ?
C7 C8 1.466(2) . ?
C8 C13 1.397(2) . ?
C8 C9 1.406(2) . ?
C9 C10 1.378(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.404(2) . ?
C10 H10 0.9300 . ?
C11 N2 1.393(2) . ?
C11 C12 1.406(2) . ?
C12 C13 1.377(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.387(2) . ?
C14 C15 1.392(2) . ?
C14 N2 1.4277(19) . ?
C15 C16 1.384(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.388(2) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.388(2) . ?
C20 C25 1.388(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.383(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.381(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.384(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.379(2) . ?
C24 H24 0.9300 . ?
C25 N2 1.4369(19) . ?

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
F2 B1 F1 109.80(14) . . ?
F2 B1 O1 110.70(14) . . ?
F1 B1 O1 110.03(14) . . ?
F2 B1 N1 109.45(14) . . ?
F1 B1 N1 106.46(13) . . ?
O1 B1 N1 110.31(13) . . ?
N1 C1 C2 121.98(16) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C1 C2 C3 118.70(17) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 119.69(18) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.20(17) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 118.93(15) . . ?
N1 C5 C6 118.14(14) . . ?
C4 C5 C6 122.93(15) . . ?
C7 C6 C5 122.20(14) . . ?
C7 C6 H6 118.9 . . ?
C5 C6 H6 118.9 . . ?
O1 C7 C6 121.14(14) . . ?
O1 C7 C8 114.11(13) . . ?
C6 C7 C8 124.71(14) . . ?
C13 C8 C9 117.40(14) . . ?
C13 C8 C7 120.81(14) . . ?
C9 C8 C7 121.68(14) . . ?
C10 C9 C8 121.38(14) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 120.79(14) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
N2 C11 C10 121.06(14) . . ?
N2 C11 C12 120.92(14) . . ?
C10 C11 C12 118.00(15) . . ?
C13 C12 C11 120.58(15) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C8 121.80(14) . . ?
C12 C13 H13 119.1 . . ?
C8 C13 H13 119.1 . . ?
C19 C14 C15 119.40(14) . . ?
C19 C14 N2 120.06(14) . . ?
C15 C14 N2 120.53(14) . . ?
C16 C15 C14 119.85(15) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 120.84(15) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 119.27(15) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C19 120.51(16) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C14 C19 C18 120.13(15) . . ?
C14 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C25 119.60(17) . . ?
C21 C20 H20 120.2 . . ?
C25 C20 H20 120.2 . . ?
C22 C21 C20 120.46(16) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C23 C22 C21 119.64(16) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 120.08(17) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 120.44(15) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C20 119.77(15) . . ?
C24 C25 N2 120.11(14) . . ?
C20 C25 N2 120.12(15) . . ?
C1 N1 C5 120.47(15) . . ?
C1 N1 B1 119.85(14) . . ?
C5 N1 B1 119.42(13) . . ?
C11 N2 C14 122.08(13) . . ?
C11 N2 C25 120.05(13) . . ?
C14 N2 C25 117.83(13) . . ?
C7 O1 B1 121.16(13) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.053
_exptl_crystal_recrystallization_method 'Vapour Deposition'
_exptl_crystal_preparation       Luminescent
