# 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_crystalclear
_database_code_depnum_ccdc_archive 'CCDC 1433056'
_audit_update_record             
;
2015-10-25 deposited with the CCDC.
2015-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        4,4'-BPy3
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H28 N6'
_chemical_formula_sum            'C42 H28 N6'
_chemical_formula_weight         616.70

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   3.7736(2)
_cell_length_b                   18.7721(13)
_cell_length_c                   20.9421(15)
_cell_angle_alpha                90
_cell_angle_beta                 95.267(5)
_cell_angle_gamma                90
_cell_volume                     1477.24(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    93
_cell_measurement_reflns_used    4468
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      30.3

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.914
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            18887
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.125
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3364
_reflns_number_gt                3073
_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       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_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)+(0.0585P)²+0.8907P] 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         3364
_refine_ls_number_parameters     238
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1212
_refine_ls_wR_factor_gt          0.1182
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.052
_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 0.5714(3) 0.06624(7) 0.20212(6) 0.0162(3) Uani 1 1 d . . . . .
C2 C 0.5958(4) 0.00138(7) 0.23512(6) 0.0171(3) Uani 1 1 d . . . . .
H2 H 0.6510 -0.0409 0.2132 0.021 Uiso 1 1 calc R U . . .
C3 C 0.5397(3) -0.00161(7) 0.30017(6) 0.0169(3) Uani 1 1 d . . . . .
C4 C 0.4496(4) 0.06085(7) 0.33126(6) 0.0177(3) Uani 1 1 d . . . . .
H4 H 0.4042 0.0587 0.3751 0.021 Uiso 1 1 calc R U . . .
C5 C 0.4246(3) 0.12630(7) 0.29948(6) 0.0168(3) Uani 1 1 d . . . . .
C6 C 0.4899(4) 0.12832(7) 0.23482(6) 0.0170(3) Uani 1 1 d . . . . .
H6 H 0.4787 0.1726 0.2127 0.020 Uiso 1 1 calc R U . . .
C7 C 0.6317(3) 0.07119(7) 0.13306(6) 0.0160(3) Uani 1 1 d . . . . .
C8 C 0.7908(4) 0.13158(7) 0.10920(6) 0.0172(3) Uani 1 1 d . . . . .
H8 H 0.8702 0.1694 0.1371 0.021 Uiso 1 1 calc R U . . .
C9 C 0.8309(4) 0.13539(7) 0.04391(6) 0.0187(3) Uani 1 1 d . . . . .
H9 H 0.9430 0.1764 0.0285 0.022 Uiso 1 1 calc R U . . .
N1 N 0.7216(3) 0.08501(6) 0.00153(5) 0.0172(2) Uani 1 1 d . . . . .
C10 C 0.5652(3) 0.02711(6) 0.02431(6) 0.0155(3) Uani 1 1 d . . . . .
C11 C 0.5212(3) 0.01767(7) 0.08936(6) 0.0163(3) Uani 1 1 d . . . . .
H11 H 0.4169 -0.0248 0.1037 0.020 Uiso 1 1 calc R U . . .
C12 C 0.5765(4) -0.06935(7) 0.33667(6) 0.0186(3) Uani 1 1 d . . . . .
C13 C 0.4551(4) -0.13385(7) 0.30963(7) 0.0225(3) Uani 1 1 d D . . . .
H13 H 0.3519 -0.1332 0.2665 0.027 Uiso 1 1 calc R U . . .
N2 N 0.4737(4) -0.19678(7) 0.34020(6) 0.0264(3) Uani 1 1 d D . . . .
C14 C 0.6215(4) -0.19656(8) 0.40073(7) 0.0272(3) Uani 1 1 d D . . . .
H14 H 0.6365 -0.2405 0.4234 0.033 Uiso 1 1 calc R U . . .
C15 C 0.7538(4) -0.13607(8) 0.43226(7) 0.0268(3) Uani 1 1 d D . . . .
H15 H 0.8577 -0.1387 0.4753 0.032 Uiso 1 1 calc R U . . .
C16 C 0.7317(4) -0.07138(8) 0.39974(7) 0.0226(3) Uani 1 1 d D . . . .
H16 H 0.8212 -0.0291 0.4202 0.027 Uiso 1 1 calc R U . . .
C17 C 0.3380(4) 0.19256(7) 0.33344(6) 0.0172(3) Uani 1 1 d . . . . .
C18A C 0.157(9) 0.2478(10) 0.2997(5) 0.0182(10) Uani 0.5 1 d D . P A 1
H18A H 0.0768 0.2401 0.2559 0.022 Uiso 0.5 1 calc R U P A 1
N3A N 0.089(4) 0.3112(6) 0.3259(3) 0.0197(8) Uani 0.5 1 d D . P A 1
C19A C 0.177(3) 0.3198(5) 0.3883(3) 0.0195(13) Uani 0.5 1 d D . P A 1
H19A H 0.1208 0.3637 0.4075 0.023 Uiso 0.5 1 calc R U P A 1
C20A C 0.347(5) 0.2680(7) 0.4267(5) 0.0205(11) Uani 0.5 1 d D . P A 1
H20A H 0.4112 0.2767 0.4709 0.025 Uiso 0.5 1 calc R U P A 1
C21A C 0.423(9) 0.2029(9) 0.3994(8) 0.0197(7) Uani 0.5 1 d D . P A 1
H21A H 0.5311 0.1657 0.4251 0.024 Uiso 0.5 1 calc R U P A 1
C18B C 0.443(9) 0.1989(9) 0.3989(7) 0.0197(7) Uani 0.5 1 d D . P A 2
H18B H 0.5739 0.1607 0.4191 0.024 Uiso 0.5 1 calc R U P A 2
N3B N 0.371(4) 0.2550(5) 0.4353(4) 0.0205(11) Uani 0.5 1 d D . P A 2
C19B C 0.211(3) 0.3107(4) 0.4050(3) 0.0183(14) Uani 0.5 1 d D . P A 2
H19B H 0.1676 0.3518 0.4295 0.022 Uiso 0.5 1 calc R U P A 2
C20B C 0.105(5) 0.3117(7) 0.3400(4) 0.0197(8) Uani 0.5 1 d D . P A 2
H20B H -0.0128 0.3521 0.3208 0.024 Uiso 0.5 1 calc R U P A 2
C21B C 0.174(9) 0.2524(10) 0.3033(5) 0.0182(10) Uani 0.5 1 d D . P A 2
H21B H 0.1110 0.2524 0.2584 0.022 Uiso 0.5 1 calc R U P A 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 1.3990(18) . ?
C1 C6 1.4001(17) . ?
C1 C7 1.4874(17) . ?
C2 C3 1.3990(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3982(18) . ?
C3 C12 1.4835(18) . ?
C4 C5 1.3963(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3989(17) . ?
C5 C17 1.4841(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3965(18) . ?
C7 C11 1.3967(18) . ?
C8 C9 1.3911(18) . ?
C8 H8 0.9500 . ?
C9 N1 1.3360(17) . ?
C9 H9 0.9500 . ?
N1 C10 1.3452(17) . ?
C10 C11 1.3985(17) . ?
C10 C10 1.491(2) 3_655 ?
C11 H11 0.9500 . ?
C12 C16 1.3954(19) . ?
C12 C13 1.3961(19) . ?
C13 N2 1.3425(18) . ?
C13 H13 0.9500 . ?
N2 C14 1.337(2) . ?
C14 C15 1.383(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18B 1.396(15) . ?
C17 C18A 1.398(17) . ?
C17 C21A 1.402(15) . ?
C17 C21B 1.403(16) . ?
C18A N3A 1.347(6) . ?
C18A H18A 0.9500 . ?
N3A C19A 1.329(6) . ?
C19A C20A 1.381(7) . ?
C19A H19A 0.9500 . ?
C20A C21A 1.391(6) . ?
C20A H20A 0.9500 . ?
C21A H21A 0.9500 . ?
C18B N3B 1.342(2) . ?
C18B H18B 0.9500 . ?
N3B C19B 1.337(2) . ?
C19B C20B 1.384(2) . ?
C19B H19B 0.9500 . ?
C20B C21B 1.391(2) . ?
C20B H20B 0.9500 . ?
C21B H21B 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
C2 C1 C6 119.35(12) . . ?
C2 C1 C7 121.70(11) . . ?
C6 C1 C7 118.94(11) . . ?
C1 C2 C3 120.46(12) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 119.00(12) . . ?
C4 C3 C12 119.61(11) . . ?
C2 C3 C12 121.38(12) . . ?
C5 C4 C3 121.64(12) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 118.36(12) . . ?
C4 C5 C17 121.15(11) . . ?
C6 C5 C17 120.48(12) . . ?
C5 C6 C1 121.14(12) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C8 C7 C11 117.50(11) . . ?
C8 C7 C1 120.51(11) . . ?
C11 C7 C1 121.94(11) . . ?
C9 C8 C7 118.85(12) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
N1 C9 C8 124.18(12) . . ?
N1 C9 H9 117.9 . . ?
C8 C9 H9 117.9 . . ?
C9 N1 C10 117.07(11) . . ?
N1 C10 C11 122.88(11) . . ?
N1 C10 C10 115.94(14) . 3_655 ?
C11 C10 C10 121.17(14) . 3_655 ?
C7 C11 C10 119.48(12) . . ?
C7 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C16 C12 C13 116.99(12) . . ?
C16 C12 C3 121.50(12) . . ?
C13 C12 C3 121.51(12) . . ?
N2 C13 C12 124.67(13) . . ?
N2 C13 H13 117.7 . . ?
C12 C13 H13 117.7 . . ?
C14 N2 C13 116.64(13) . . ?
N2 C14 C15 123.77(13) . . ?
N2 C14 H14 118.1 . . ?
C15 C14 H14 118.1 . . ?
C14 C15 C16 118.69(13) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C15 C16 C12 119.23(13) . . ?
C15 C16 H16 120.4 . . ?
C12 C16 H16 120.4 . . ?
C18A C17 C21A 117.0(7) . . ?
C18B C17 C21B 116.5(6) . . ?
C18B C17 C5 119.2(4) . . ?
C18A C17 C5 119.9(4) . . ?
C21A C17 C5 123.2(4) . . ?
C21B C17 C5 124.2(4) . . ?
N3A C18A C17 123.6(6) . . ?
N3A C18A H18A 118.2 . . ?
C17 C18A H18A 118.2 . . ?
C19A N3A C18A 117.9(4) . . ?
N3A C19A C20A 123.2(4) . . ?
N3A C19A H19A 118.4 . . ?
C20A C19A H19A 118.4 . . ?
C19A C20A C21A 118.9(4) . . ?
C19A C20A H20A 120.6 . . ?
C21A C20A H20A 120.6 . . ?
C20A C21A C17 119.2(6) . . ?
C20A C21A H21A 120.4 . . ?
C17 C21A H21A 120.4 . . ?
N3B C18B C17 124.9(6) . . ?
N3B C18B H18B 117.6 . . ?
C17 C18B H18B 117.6 . . ?
C19B N3B C18B 116.7(2) . . ?
N3B C19B C20B 123.73(19) . . ?
N3B C19B H19B 118.1 . . ?
C20B C19B H19B 118.1 . . ?
C19B C20B C21B 118.7(2) . . ?
C19B C20B H20B 120.7 . . ?
C21B C20B H20B 120.7 . . ?
C20B C21B C17 119.3(5) . . ?
C20B C21B H21B 120.3 . . ?
C17 C21B H21B 120.3 . . ?

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
C6 C1 C2 C3 0.0(2) . . . . ?
C7 C1 C2 C3 179.64(12) . . . . ?
C1 C2 C3 C4 1.67(19) . . . . ?
C1 C2 C3 C12 -177.86(12) . . . . ?
C2 C3 C4 C5 -1.9(2) . . . . ?
C12 C3 C4 C5 177.64(12) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C3 C4 C5 C17 -178.38(12) . . . . ?
C4 C5 C6 C1 1.3(2) . . . . ?
C17 C5 C6 C1 -179.91(12) . . . . ?
C2 C1 C6 C5 -1.5(2) . . . . ?
C7 C1 C6 C5 178.86(12) . . . . ?
C2 C1 C7 C8 -145.70(13) . . . . ?
C6 C1 C7 C8 33.97(19) . . . . ?
C2 C1 C7 C11 36.78(19) . . . . ?
C6 C1 C7 C11 -143.55(13) . . . . ?
C11 C7 C8 C9 -0.02(19) . . . . ?
C1 C7 C8 C9 -177.65(12) . . . . ?
C7 C8 C9 N1 1.0(2) . . . . ?
C8 C9 N1 C10 -0.4(2) . . . . ?
C9 N1 C10 C11 -1.30(19) . . . . ?
C9 N1 C10 C10 177.99(14) . . . 3_655 ?
C8 C7 C11 C10 -1.51(19) . . . . ?
C1 C7 C11 C10 176.08(12) . . . . ?
N1 C10 C11 C7 2.3(2) . . . . ?
C10 C10 C11 C7 -176.98(14) 3_655 . . . ?
C4 C3 C12 C16 -38.87(19) . . . . ?
C2 C3 C12 C16 140.66(14) . . . . ?
C4 C3 C12 C13 140.64(14) . . . . ?
C2 C3 C12 C13 -39.83(19) . . . . ?
C16 C12 C13 N2 0.8(2) . . . . ?
C3 C12 C13 N2 -178.71(13) . . . . ?
C12 C13 N2 C14 -0.3(2) . . . . ?
C13 N2 C14 C15 -0.3(2) . . . . ?
N2 C14 C15 C16 0.3(2) . . . . ?
C14 C15 C16 C12 0.2(2) . . . . ?
C13 C12 C16 C15 -0.7(2) . . . . ?
C3 C12 C16 C15 178.80(13) . . . . ?
C4 C5 C17 C18B 30.3(18) . . . . ?
C6 C5 C17 C18B -148.5(18) . . . . ?
C4 C5 C17 C18A -150.2(17) . . . . ?
C6 C5 C17 C18A 31.0(17) . . . . ?
C4 C5 C17 C21A 28.4(19) . . . . ?
C6 C5 C17 C21A -150.4(19) . . . . ?
C4 C5 C17 C21B -153.8(18) . . . . ?
C6 C5 C17 C21B 27.4(18) . . . . ?
C21A C17 C18A N3A 6(4) . . . . ?
C5 C17 C18A N3A -175(2) . . . . ?
C17 C18A N3A C19A -5(4) . . . . ?
C18A N3A C19A C20A 3(3) . . . . ?
N3A C19A C20A C21A -2(3) . . . . ?
C19A C20A C21A C17 3(4) . . . . ?
C18A C17 C21A C20A -4(4) . . . . ?
C5 C17 C21A C20A 176.9(19) . . . . ?
C21B C17 C18B N3B 6(4) . . . . ?
C5 C17 C18B N3B -178(2) . . . . ?
C17 C18B N3B C19B -5(4) . . . . ?
C18B N3B C19B C20B 3(3) . . . . ?
N3B C19B C20B C21B -1(3) . . . . ?
C19B C20B C21B C17 2(4) . . . . ?
C18B C17 C21B C20B -4(4) . . . . ?
C5 C17 C21B C20B 179.9(18) . . . . ?

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.050



####################################################################### 
# 
# 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_ydkr2
_database_code_depnum_ccdc_archive 'CCDC 1433057'
_audit_update_record             
;
2015-11-23 deposited with the CCDC.
2015-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        6,6'-BPy3
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C42 H28 N6'
_chemical_formula_sum            'C42 H28 N6'
_chemical_formula_weight         616.70

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'

_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                   32.776(12)
_cell_length_b                   3.8953(14)
_cell_length_c                   23.750(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.426(5)
_cell_angle_gamma                90
_cell_volume                     3018.6(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    93
_cell_measurement_reflns_used    3191
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      30.6

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD area detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            18153
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.447
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3437
_reflns_number_gt                2946
_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       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_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)+(0.0676P)²+1.9894P] 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         3437
_refine_ls_number_parameters     235
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1316
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.091
_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
N1 N 0.20218(3) 0.0801(3) 0.46835(5) 0.0210(3) Uani 1 1 d . . . . .
N2 N 0.14909(4) -0.7032(4) 0.19594(5) 0.0361(3) Uani 1 1 d . . . . .
C1 C 0.22846(4) 0.2312(4) 0.50737(5) 0.0209(3) Uani 1 1 d . . . . .
C2 C 0.21651(4) 0.3518(4) 0.55865(5) 0.0244(3) Uani 1 1 d . . . . .
H2 H 0.2357 0.4592 0.5855 0.029 Uiso 1 1 calc R U . . .
C3 C 0.17609(4) 0.3117(4) 0.56954(6) 0.0275(3) Uani 1 1 d . . . . .
H3 H 0.1671 0.3931 0.6040 0.033 Uiso 1 1 calc R U . . .
C4 C 0.14880(4) 0.1517(4) 0.52970(6) 0.0266(3) Uani 1 1 d . . . . .
H4 H 0.1210 0.1181 0.5367 0.032 Uiso 1 1 calc R U . . .
C5 C 0.16287(4) 0.0409(4) 0.47911(5) 0.0217(3) Uani 1 1 d . . . . .
C6 C 0.18614(5) -0.8476(4) 0.20739(7) 0.0345(4) Uani 1 1 d D . . . .
H6 H 0.1993 -0.9408 0.1768 0.041 Uiso 1 1 calc R U . . .
C7 C 0.20625(5) -0.8685(4) 0.26099(7) 0.0307(3) Uani 1 1 d D . . . .
H7 H 0.2324 -0.9738 0.2671 0.037 Uiso 1 1 calc R U . . .
C8 C 0.18733(4) -0.7323(4) 0.30546(6) 0.0261(3) Uani 1 1 d D . . . .
H8 H 0.2006 -0.7431 0.3428 0.031 Uiso 1 1 calc R U . . .
C9 C 0.14888(4) -0.5790(4) 0.29588(5) 0.0221(3) Uani 1 1 d D . . . .
C10 C 0.13126(5) -0.5723(4) 0.24006(6) 0.0293(3) Uani 1 1 d D . . . .
H10 H 0.1050 -0.4690 0.2327 0.035 Uiso 1 1 calc R U . . .
C11 C 0.12868(4) -0.4193(4) 0.34252(5) 0.0213(3) Uani 1 1 d . . . . .
C12 C 0.15268(4) -0.2865(4) 0.38920(5) 0.0212(3) Uani 1 1 d . . . . .
H12 H 0.1816 -0.3095 0.3910 0.025 Uiso 1 1 calc R U . . .
C13 C 0.13528(4) -0.1212(4) 0.43316(5) 0.0215(3) Uani 1 1 d . . . . .
C14 C 0.09273(4) -0.0967(4) 0.43109(6) 0.0226(3) Uani 1 1 d . . . . .
H14 H 0.0805 0.0096 0.4613 0.027 Uiso 1 1 calc R U . . .
C15 C 0.06794(4) -0.2276(4) 0.38481(6) 0.0225(3) Uani 1 1 d . . . . .
C16 C 0.08614(4) -0.3864(4) 0.34083(5) 0.0225(3) Uani 1 1 d . . . . .
H16 H 0.0693 -0.4736 0.3093 0.027 Uiso 1 1 calc R U . . .
C17A C 0.0211(3) -0.152(4) 0.3835(5) 0.0192(15) Uani 0.5 1 d D . P A 1
C18A C 0.0009(4) -0.055(4) 0.3324(5) 0.0245(18) Uani 0.5 1 d D . P A 1
H18A H 0.0157 -0.0098 0.3006 0.029 Uiso 0.5 1 calc R U P A 1
C19A C -0.0412(4) -0.025(9) 0.3287(5) 0.0491(17) Uani 0.5 1 d D . P A 1
H19A H -0.0559 0.0397 0.2939 0.059 Uiso 0.5 1 calc R U P A 1
C20A C -0.0622(3) -0.090(8) 0.3760(5) 0.0639(9) Uani 0.5 1 d D . P A 1
H20A H -0.0912 -0.1028 0.3734 0.077 Uiso 0.5 1 calc R U P A 1
N3A N -0.0384(3) -0.135(3) 0.4273(4) 0.046(2) Uani 0.5 1 d D . P A 1
C21A C 0.0009(6) -0.190(5) 0.4308(8) 0.033(2) Uani 0.5 1 d . . P A 1
H21A H 0.0154 -0.2547 0.4657 0.039 Uiso 0.5 1 calc R U P A 1
C17B C 0.0245(3) -0.216(4) 0.3794(5) 0.0192(15) Uani 0.5 1 d D . P A 2
C18B C 0.0009(6) -0.265(5) 0.4257(8) 0.033(2) Uani 0.5 1 d D . P A 2
H18B H 0.0154 -0.3263 0.4608 0.039 Uiso 0.5 1 calc R U P A 2
C19B C -0.0426(4) -0.230(4) 0.4252(5) 0.046(2) Uani 0.5 1 d D . P A 2
H19B H -0.0583 -0.2973 0.4550 0.055 Uiso 0.5 1 calc R U P A 2
C20B C -0.0579(3) -0.085(8) 0.3755(6) 0.0639(9) Uani 0.5 1 d D . P A 2
H20B H -0.0844 0.0126 0.3754 0.077 Uiso 0.5 1 calc R U P A 2
N3B N -0.0405(3) -0.061(7) 0.3261(4) 0.0491(17) Uani 0.5 1 d D . P A 2
C21B C 0.0001(4) -0.127(4) 0.3294(5) 0.0245(18) Uani 0.5 1 d . . P A 2
H21B H 0.0133 -0.1125 0.2955 0.029 Uiso 0.5 1 calc R U P A 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
N1 C1 1.3401(17) . ?
N1 C5 1.3459(18) . ?
N2 C6 1.343(2) . ?
N2 C10 1.347(2) . ?
C1 C2 1.3955(19) . ?
C1 C1 1.494(3) 7_556 ?
C2 C3 1.383(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3956(19) . ?
C4 H4 0.9500 . ?
C5 C13 1.4902(18) . ?
C6 C7 1.380(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.3953(19) . ?
C9 C11 1.4802(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.3966(18) . ?
C11 C16 1.3970(19) . ?
C12 C13 1.3935(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.3943(19) . ?
C14 C15 1.3996(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.396(2) . ?
C15 C17B 1.418(10) . ?
C15 C17A 1.561(9) . ?
C16 H16 0.9500 . ?
C17A C21A 1.362(17) . ?
C17A C18A 1.380(2) . ?
C18A C19A 1.381(2) . ?
C18A H18A 0.9500 . ?
C19A C20A 1.394(2) . ?
C19A H19A 0.9500 . ?
C20A N3A 1.395(2) . ?
C20A H20A 0.9500 . ?
N3A C21A 1.300(16) . ?
C21A H21A 0.9500 . ?
C17B C21B 1.411(5) . ?
C17B C18B 1.417(17) . ?
C18B C19B 1.429(16) . ?
C18B H18B 0.9500 . ?
C19B C20B 1.361(10) . ?
C19B H19B 0.9500 . ?
C20B N3B 1.357(7) . ?
C20B H20B 0.9500 . ?
N3B C21B 1.350(6) . ?
C21B H21B 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
C1 N1 C5 118.88(12) . . ?
C6 N2 C10 116.84(13) . . ?
N1 C1 C2 122.43(12) . . ?
N1 C1 C1 116.16(15) . 7_556 ?
C2 C1 C1 121.40(15) . 7_556 ?
C3 C2 C1 118.56(12) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 119.40(13) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 118.82(13) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 121.90(12) . . ?
N1 C5 C13 115.77(12) . . ?
C4 C5 C13 122.32(12) . . ?
N2 C6 C7 123.75(14) . . ?
N2 C6 H6 118.1 . . ?
C7 C6 H6 118.1 . . ?
C6 C7 C8 118.27(15) . . ?
C6 C7 H7 120.9 . . ?
C8 C7 H7 120.9 . . ?
C7 C8 C9 120.30(14) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 116.73(13) . . ?
C8 C9 C11 121.29(12) . . ?
C10 C9 C11 121.93(13) . . ?
N2 C10 C9 124.12(14) . . ?
N2 C10 H10 117.9 . . ?
C9 C10 H10 117.9 . . ?
C12 C11 C16 118.33(12) . . ?
C12 C11 C9 119.44(12) . . ?
C16 C11 C9 122.20(12) . . ?
C13 C12 C11 121.75(12) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C14 118.95(12) . . ?
C12 C13 C5 118.79(12) . . ?
C14 C13 C5 122.17(12) . . ?
C13 C14 C15 120.48(13) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 119.46(12) . . ?
C16 C15 C17B 116.2(5) . . ?
C14 C15 C17B 124.3(5) . . ?
C16 C15 C17A 123.9(5) . . ?
C14 C15 C17A 116.3(5) . . ?
C15 C16 C11 121.01(12) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
C21A C17A C18A 121.8(8) . . ?
C21A C17A C15 121.1(12) . . ?
C18A C17A C15 117.2(8) . . ?
C17A C18A C19A 118.1(2) . . ?
C17A C18A H18A 121.0 . . ?
C19A C18A H18A 121.0 . . ?
C18A C19A C20A 120.0(2) . . ?
C18A C19A H19A 120.0 . . ?
C20A C19A H19A 120.0 . . ?
C19A C20A N3A 116.6(2) . . ?
C19A C20A H20A 121.7 . . ?
N3A C20A H20A 121.7 . . ?
C21A N3A C20A 123.1(9) . . ?
N3A C21A C17A 118.9(15) . . ?
N3A C21A H21A 120.5 . . ?
C17A C21A H21A 120.5 . . ?
C21B C17B C18B 112.3(8) . . ?
C21B C17B C15 124.6(9) . . ?
C18B C17B C15 122.9(12) . . ?
C17B C18B C19B 126.7(15) . . ?
C17B C18B H18B 116.6 . . ?
C19B C18B H18B 116.6 . . ?
C20B C19B C18B 109.4(10) . . ?
C20B C19B H19B 125.3 . . ?
C18B C19B H19B 125.3 . . ?
N3B C20B C19B 129.0(10) . . ?
N3B C20B H20B 115.5 . . ?
C19B C20B H20B 115.5 . . ?
C21B N3B C20B 115.4(4) . . ?
N3B C21B C17B 124.9(4) . . ?
N3B C21B H21B 117.6 . . ?
C17B C21B H21B 117.6 . . ?

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
C5 N1 C1 C2 -0.5(2) . . . . ?
C5 N1 C1 C1 -179.62(14) . . . 7_556 ?
N1 C1 C2 C3 0.4(2) . . . . ?
C1 C1 C2 C3 179.46(16) 7_556 . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C2 C3 C4 C5 -1.2(2) . . . . ?
C1 N1 C5 C4 -0.2(2) . . . . ?
C1 N1 C5 C13 178.53(12) . . . . ?
C3 C4 C5 N1 1.1(2) . . . . ?
C3 C4 C5 C13 -177.63(13) . . . . ?
C10 N2 C6 C7 0.2(2) . . . . ?
N2 C6 C7 C8 -0.2(3) . . . . ?
C6 C7 C8 C9 0.1(2) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C7 C8 C9 C11 -177.62(13) . . . . ?
C6 N2 C10 C9 0.0(2) . . . . ?
C8 C9 C10 N2 0.0(2) . . . . ?
C11 C9 C10 N2 177.57(14) . . . . ?
C8 C9 C11 C12 27.7(2) . . . . ?
C10 C9 C11 C12 -149.80(14) . . . . ?
C8 C9 C11 C16 -154.35(14) . . . . ?
C10 C9 C11 C16 28.1(2) . . . . ?
C16 C11 C12 C13 -0.7(2) . . . . ?
C9 C11 C12 C13 177.35(13) . . . . ?
C11 C12 C13 C14 1.8(2) . . . . ?
C11 C12 C13 C5 -174.70(12) . . . . ?
N1 C5 C13 C12 13.99(19) . . . . ?
C4 C5 C13 C12 -167.24(14) . . . . ?
N1 C5 C13 C14 -162.41(13) . . . . ?
C4 C5 C13 C14 16.4(2) . . . . ?
C12 C13 C14 C15 -1.8(2) . . . . ?
C5 C13 C14 C15 174.61(13) . . . . ?
C13 C14 C15 C16 0.6(2) . . . . ?
C13 C14 C15 C17B 179.5(8) . . . . ?
C13 C14 C15 C17A -173.6(7) . . . . ?
C14 C15 C16 C11 0.5(2) . . . . ?
C17B C15 C16 C11 -178.4(7) . . . . ?
C17A C15 C16 C11 174.3(7) . . . . ?
C12 C11 C16 C15 -0.5(2) . . . . ?
C9 C11 C16 C15 -178.48(13) . . . . ?
C16 C15 C17A C21A 141.4(12) . . . . ?
C14 C15 C17A C21A -44.7(15) . . . . ?
C16 C15 C17A C18A -37.0(15) . . . . ?
C14 C15 C17A C18A 137.0(10) . . . . ?
C21A C17A C18A C19A -6(3) . . . . ?
C15 C17A C18A C19A 172.7(19) . . . . ?
C17A C18A C19A C20A 0(3) . . . . ?
C18A C19A C20A N3A 9(4) . . . . ?
C19A C20A N3A C21A -15(3) . . . . ?
C20A N3A C21A C17A 10(3) . . . . ?
C18A C17A C21A N3A 1(2) . . . . ?
C15 C17A C21A N3A -177.7(13) . . . . ?
C16 C15 C17B C21B -44.8(16) . . . . ?
C14 C15 C17B C21B 136.4(11) . . . . ?
C16 C15 C17B C18B 141.1(12) . . . . ?
C14 C15 C17B C18B -37.8(17) . . . . ?
C21B C17B C18B C19B 0(2) . . . . ?
C15 C17B C18B C19B 174.5(14) . . . . ?
C17B C18B C19B C20B -10(2) . . . . ?
C18B C19B C20B N3B 19(3) . . . . ?
C19B C20B N3B C21B -14(3) . . . . ?
C20B N3B C21B C17B 0(3) . . . . ?
C18B C17B C21B N3B 6(3) . . . . ?
C15 C17B C21B N3B -168.6(18) . . . . ?

_refine_diff_density_max         0.323
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.049



