# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_ph-htx
_database_code_depnum_ccdc_archive 'CCDC 1579239'
_audit_update_record             
;
2017-10-11 deposited with the CCDC.
2018-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        "9, 9'-diphenyl-9H, 9'H-3, 3'-bicarbazole"
_chemical_name_common            BPhCz
_chemical_melting_point          208
_chemical_formula_moiety         'C36 H24 N2'
_chemical_formula_sum            'C36 H24 N2'
_chemical_formula_weight         484.57

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   9.4067(11)
_cell_length_b                   9.6150(11)
_cell_length_c                   14.1821(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.252(3)
_cell_angle_gamma                90.00
_cell_volume                     1243.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2058
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      21.1

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9910
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_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  'Bruker Smart Aepex CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9584
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         28.22
_reflns_number_total             3002
_reflns_number_gt                2567
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0401P)²+0.4387P] 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         3002
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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 0.28194(14) 0.40648(13) 0.24779(9) 0.0373(3) Uani 1 1 d . . .
C2 C 0.25519(15) 0.53123(15) 0.19601(10) 0.0440(3) Uani 1 1 d . . .
H2 H 0.1805 0.5386 0.1394 0.053 Uiso 1 1 calc R . .
C3 C 0.34366(16) 0.64308(15) 0.23188(11) 0.0474(3) Uani 1 1 d . . .
H3 H 0.3270 0.7275 0.1991 0.057 Uiso 1 1 calc R . .
C4 C 0.45716(16) 0.63358(15) 0.31563(11) 0.0461(3) Uani 1 1 d . . .
H4 H 0.5157 0.7108 0.3371 0.055 Uiso 1 1 calc R . .
C5 C 0.48385(15) 0.51012(14) 0.36743(10) 0.0409(3) Uani 1 1 d . . .
H5 H 0.5598 0.5038 0.4234 0.049 Uiso 1 1 calc R . .
C6 C 0.39472(13) 0.39550(13) 0.33403(9) 0.0347(3) Uani 1 1 d . . .
C7 C 0.38898(13) 0.25439(12) 0.36914(9) 0.0333(3) Uani 1 1 d . . .
C8 C 0.47725(13) 0.18148(13) 0.44669(8) 0.0343(3) Uani 1 1 d . . .
H8 H 0.5533 0.2270 0.4901 0.041 Uiso 1 1 calc R . .
C9 C 0.45217(13) 0.04059(12) 0.45965(8) 0.0348(3) Uani 1 1 d . . .
C10 C 0.33390(16) -0.02286(14) 0.39285(10) 0.0456(3) Uani 1 1 d . . .
H10 H 0.3148 -0.1163 0.4015 0.055 Uiso 1 1 calc R . .
C11 C 0.24517(16) 0.04689(14) 0.31532(10) 0.0459(3) Uani 1 1 d . . .
H11 H 0.1683 0.0018 0.2724 0.055 Uiso 1 1 calc R . .
C12 C 0.27433(14) 0.18692(13) 0.30338(9) 0.0370(3) Uani 1 1 d . . .
C13 C 0.10145(14) 0.24217(14) 0.14339(9) 0.0391(3) Uani 1 1 d . . .
C14 C -0.02744(15) 0.17939(16) 0.15120(11) 0.0468(3) Uani 1 1 d . . .
H14 H -0.0461 0.1669 0.2121 0.056 Uiso 1 1 calc R . .
C15 C -0.12848(16) 0.13529(18) 0.06865(12) 0.0553(4) Uani 1 1 d . . .
H15 H -0.2144 0.0919 0.0742 0.066 Uiso 1 1 calc R . .
C16 C -0.10263(18) 0.15519(19) -0.02193(12) 0.0602(4) Uani 1 1 d . . .
H16 H -0.1703 0.1244 -0.0774 0.072 Uiso 1 1 calc R . .
C17 C 0.02410(19) 0.2210(2) -0.02974(11) 0.0609(4) Uani 1 1 d . . .
H17 H 0.0402 0.2369 -0.0909 0.073 Uiso 1 1 calc R . .
C18 C 0.12765(16) 0.26367(17) 0.05236(11) 0.0499(4) Uani 1 1 d . . .
H18 H 0.2139 0.3063 0.0466 0.060 Uiso 1 1 calc R . .
N1 N 0.20844(12) 0.27956(12) 0.22954(8) 0.0408(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0362(6) 0.0376(6) 0.0393(6) 0.0085(5) 0.0119(5) 0.0050(5)
C2 0.0436(7) 0.0433(7) 0.0456(7) 0.0144(6) 0.0117(6) 0.0088(6)
C3 0.0509(8) 0.0398(7) 0.0555(8) 0.0169(6) 0.0207(6) 0.0066(6)
C4 0.0475(7) 0.0388(7) 0.0556(8) 0.0077(6) 0.0199(6) -0.0022(6)
C5 0.0405(6) 0.0386(7) 0.0445(7) 0.0055(5) 0.0122(5) 0.0012(5)
C6 0.0356(6) 0.0344(6) 0.0362(6) 0.0067(5) 0.0129(5) 0.0054(5)
C7 0.0349(6) 0.0323(6) 0.0340(6) 0.0042(4) 0.0109(5) 0.0039(5)
C8 0.0366(6) 0.0332(6) 0.0323(6) 0.0028(4) 0.0073(5) 0.0021(5)
C9 0.0376(6) 0.0321(6) 0.0338(6) 0.0039(5) 0.0071(5) 0.0049(5)
C10 0.0501(8) 0.0322(6) 0.0472(7) 0.0067(5) -0.0017(6) -0.0010(5)
C11 0.0463(7) 0.0382(7) 0.0451(7) 0.0052(5) -0.0044(6) -0.0022(6)
C12 0.0373(6) 0.0368(6) 0.0356(6) 0.0067(5) 0.0065(5) 0.0050(5)
C13 0.0343(6) 0.0415(7) 0.0391(6) 0.0088(5) 0.0043(5) 0.0071(5)
C14 0.0369(7) 0.0576(8) 0.0459(7) 0.0098(6) 0.0101(5) 0.0038(6)
C15 0.0347(7) 0.0621(10) 0.0638(10) 0.0110(8) 0.0023(6) -0.0001(6)
C16 0.0522(9) 0.0656(10) 0.0512(9) 0.0083(8) -0.0095(7) 0.0028(8)
C17 0.0631(10) 0.0783(12) 0.0378(7) 0.0149(7) 0.0058(7) 0.0014(9)
C18 0.0422(7) 0.0620(9) 0.0449(7) 0.0145(7) 0.0095(6) 0.0000(6)
N1 0.0408(6) 0.0388(6) 0.0388(6) 0.0110(4) 0.0024(4) 0.0026(4)

_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 N1 1.3950(17) . ?
C1 C2 1.3965(17) . ?
C1 C6 1.4119(18) . ?
C2 C3 1.378(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3860(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.3951(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.4509(16) . ?
C7 C8 1.3932(16) . ?
C7 C12 1.3994(18) . ?
C8 C9 1.3950(17) . ?
C8 H8 0.9300 . ?
C9 C10 1.4101(18) . ?
C9 C9 1.491(2) 3_656 ?
C10 C11 1.3797(18) . ?
C10 H10 0.9300 . ?
C11 C12 1.3926(19) . ?
C11 H11 0.9300 . ?
C12 N1 1.3981(15) . ?
C13 C14 1.3830(19) . ?
C13 C18 1.3881(19) . ?
C13 N1 1.4246(17) . ?
C14 C15 1.381(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(2) . ?
C17 H17 0.9300 . ?
C18 H18 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
N1 C1 C2 129.56(12) . . ?
N1 C1 C6 109.13(10) . . ?
C2 C1 C6 121.29(12) . . ?
C3 C2 C1 117.51(13) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 122.05(13) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 120.65(13) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 118.77(13) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 119.71(11) . . ?
C5 C6 C7 133.81(12) . . ?
C1 C6 C7 106.48(11) . . ?
C8 C7 C12 120.30(11) . . ?
C8 C7 C6 132.54(12) . . ?
C12 C7 C6 107.01(10) . . ?
C7 C8 C9 120.35(12) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 117.56(11) . . ?
C8 C9 C9 121.33(14) . 3_656 ?
C10 C9 C9 121.10(14) . 3_656 ?
C11 C10 C9 123.20(12) . . ?
C11 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
C10 C11 C12 117.92(13) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
C11 C12 N1 130.00(12) . . ?
C11 C12 C7 120.64(11) . . ?
N1 C12 C7 109.30(11) . . ?
C14 C13 C18 119.96(13) . . ?
C14 C13 N1 119.31(12) . . ?
C18 C13 N1 120.69(12) . . ?
C15 C14 C13 120.01(14) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 120.34(14) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 119.56(15) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.82(15) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C13 119.28(14) . . ?
C17 C18 H18 120.4 . . ?
C13 C18 H18 120.4 . . ?
C1 N1 C12 108.08(10) . . ?
C1 N1 C13 126.38(10) . . ?
C12 N1 C13 124.81(11) . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        28.22
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.034
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM&PE'
