#------------------------------------------------------------------------------
#$Date: 2019-11-25 06:33:16 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240240 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/95/4129537.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4129537
loop_
_publ_author_name
'Kawasumi, Katsuaki'
'Wu, Tony'
'Zhu, Tianyu'
'Chae, Hyun Sik'
'Van Voorhis, Troy'
'Baldo, Marc A.'
'Swager, Timothy M.'
_publ_section_title
;
 Thermally Activated Delayed Fluorescence Materials Based on
 Homoconjugation Effect of Donor-Acceptor Triptycenes.
;
_journal_issue                   37
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11908
_journal_page_last               11911
_journal_paper_doi               10.1021/jacs.5b07932
_journal_volume                  137
_journal_year                    2015
_chemical_formula_sum            'C48 H30 N6'
_chemical_formula_weight         690.78
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.089(6)
_cell_length_b                   11.878(4)
_cell_length_c                   14.200(4)
_cell_measurement_reflns_used    3294
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.30
_cell_measurement_theta_min      3.02
_cell_volume                     3388.4(18)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2011)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27821
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         1.992
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7026
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3342
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0606
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0788P)²+2.8621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1569
_refine_ls_wR_factor_ref         0.1800
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2291
_reflns_number_total             3342
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b07932_si_002.cif
_cod_data_source_block           x15029
_cod_original_cell_volume        3388.4(17)
_cod_database_code               4129537
_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. 
;
_shelx_estimated_absorpt_t_min   0.992
_shelx_estimated_absorpt_t_max   0.996
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
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
N1 N 0.47337(11) 0.62536(18) 0.34402(16) 0.0332(5) Uani 1 1 d . .
C21 C 0.49093(14) 0.9269(2) 0.2980(2) 0.0422(7) Uani 1 1 d . U
C24 C 0.48695(15) 1.0381(3) 0.3497(2) 0.0482(8) Uani 1 1 d . U
N4 N 0.48272(17) 1.1087(3) 0.3946(3) 0.0798(11) Uani 1 1 d . U
N5 N 0.73014(11) 0.21134(19) 0.27310(16) 0.0387(6) Uani 1 1 d . .
C1 C 0.66770(13) 0.2635(2) 0.2928(2) 0.0348(6) Uani 1 1 d . .
C2 C 0.63125(13) 0.3094(2) 0.21901(19) 0.0322(6) Uani 1 1 d . .
H2 H 0.6484 0.3074 0.1567 0.039 Uiso 1 1 calc R U
C3 C 0.56965(12) 0.3583(2) 0.23678(18) 0.0306(6) Uani 1 1 d . .
C11 C 0.47533(12) 0.4161(2) 0.33519(18) 0.0295(6) Uani 1 1 d . .
H11 H 0.4566 0.4154 0.4004 0.035 Uiso 1 1 calc R U
C12 C 0.54414(12) 0.3615(2) 0.32867(18) 0.0299(6) Uani 1 1 d . .
C13 C 0.58122(13) 0.3189(2) 0.40265(19) 0.0330(6) Uani 1 1 d . .
H13 H 0.5649 0.3234 0.4653 0.040 Uiso 1 1 calc R U
C14 C 0.64286(14) 0.2695(2) 0.3844(2) 0.0364(6) Uani 1 1 d . .
H14 H 0.6682 0.2395 0.4350 0.044 Uiso 1 1 calc R U
C16 C 0.48586(12) 0.5338(2) 0.29701(18) 0.0294(6) Uani 1 1 d . .
C17 C 0.48775(12) 0.7240(2) 0.2962(2) 0.0341(6) Uani 1 1 d . .
C22 C 0.47902(14) 0.8268(2) 0.3442(2) 0.0406(7) Uani 1 1 d . .
H22 H 0.4650 0.8271 0.4081 0.049 Uiso 1 1 calc R U
C31 C 0.78392(13) 0.2202(2) 0.33725(19) 0.0348(6) Uani 1 1 d . .
C32 C 0.82494(14) 0.1277(2) 0.3556(2) 0.0412(7) Uani 1 1 d . .
H32 H 0.8175 0.0578 0.3249 0.049 Uiso 1 1 calc R U
C33 C 0.87620(14) 0.1394(3) 0.4187(2) 0.0413(7) Uani 1 1 d . .
H33 H 0.9038 0.0763 0.4315 0.050 Uiso 1 1 calc R U
C34 C 0.88896(14) 0.2382(3) 0.4636(2) 0.0438(7) Uani 1 1 d . .
H34 H 0.9251 0.2440 0.5065 0.053 Uiso 1 1 calc R U
C35 C 0.84858(14) 0.3298(3) 0.4460(2) 0.0418(7) Uani 1 1 d . .
H35 H 0.8566 0.3988 0.4777 0.050 Uiso 1 1 calc R U
C36 C 0.79631(14) 0.3221(2) 0.3824(2) 0.0403(7) Uani 1 1 d . .
H36 H 0.7692 0.3858 0.3698 0.048 Uiso 1 1 calc R U
C41 C 0.73270(13) 0.1257(2) 0.20265(19) 0.0359(6) Uani 1 1 d . .
C42 C 0.68482(15) 0.0422(2) 0.1990(2) 0.0437(7) Uani 1 1 d . .
H42 H 0.6477 0.0442 0.2403 0.052 Uiso 1 1 calc R U
C43 C 0.69168(16) -0.0453(2) 0.1337(2) 0.0482(8) Uani 1 1 d . .
H43 H 0.6592 -0.1034 0.1317 0.058 Uiso 1 1 calc R U
C44 C 0.74379(15) -0.0485(3) 0.0734(2) 0.0471(8) Uani 1 1 d . .
H44 H 0.7477 -0.1084 0.0294 0.057 Uiso 1 1 calc R U
C45 C 0.79189(15) 0.0368(2) 0.0760(2) 0.0435(7) Uani 1 1 d . .
H45 H 0.8284 0.0350 0.0335 0.052 Uiso 1 1 calc R U
C46 C 0.78637(15) 0.1232(2) 0.1402(2) 0.0403(7) Uani 1 1 d . .
H46 H 0.8190 0.1811 0.1420 0.048 Uiso 1 1 calc R U
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'
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
C16 N1 C17 114.6(2) . .
C22 C21 C21 120.29(18) . 3_655
C22 C21 C24 120.9(3) . .
C21 C21 C24 118.81(18) 3_655 .
N4 C24 C21 171.6(4) . .
C31 N5 C1 120.8(2) . .
C31 N5 C41 118.4(2) . .
C1 N5 C41 118.6(2) . .
C2 C1 C14 119.6(2) . .
C2 C1 N5 119.0(2) . .
C14 C1 N5 121.3(2) . .
C3 C2 C1 119.7(2) . .
C3 C2 H2 120.1 . .
C1 C2 H2 120.1 . .
C2 C3 C12 120.4(2) . .
C2 C3 C11 126.4(2) . 3_655
C12 C3 C11 113.2(2) . 3_655
C16 C11 C3 105.0(2) . 3_655
C16 C11 C12 104.11(19) . .
C3 C11 C12 107.6(2) 3_655 .
C16 C11 H11 113.1 . .
C3 C11 H11 113.1 3_655 .
C12 C11 H11 113.1 . .
C13 C12 C3 120.0(2) . .
C13 C12 C11 126.6(2) . .
C3 C12 C11 113.4(2) . .
C12 C13 C14 119.4(2) . .
C12 C13 H13 120.3 . .
C14 C13 H13 120.3 . .
C1 C14 C13 120.8(3) . .
C1 C14 H14 119.6 . .
C13 C14 H14 119.6 . .
N1 C16 C16 123.21(15) . 3_655
N1 C16 C11 124.1(2) . .
C16 C16 C11 112.61(14) 3_655 .
N1 C17 C17 122.15(15) . 3_655
N1 C17 C22 118.1(3) . .
C17 C17 C22 119.76(17) 3_655 .
C21 C22 C17 119.7(3) . .
C21 C22 H22 120.1 . .
C17 C22 H22 120.1 . .
C36 C31 C32 119.5(3) . .
C36 C31 N5 119.8(2) . .
C32 C31 N5 120.8(3) . .
C33 C32 C31 119.0(3) . .
C33 C32 H32 120.5 . .
C31 C32 H32 120.5 . .
C34 C33 C32 122.4(3) . .
C34 C33 H33 118.8 . .
C32 C33 H33 118.8 . .
C33 C34 C35 119.0(3) . .
C33 C34 H34 120.5 . .
C35 C34 H34 120.5 . .
C34 C35 C36 120.7(3) . .
C34 C35 H35 119.6 . .
C36 C35 H35 119.6 . .
C35 C36 C31 119.5(3) . .
C35 C36 H36 120.3 . .
C31 C36 H36 120.3 . .
C42 C41 C46 119.9(3) . .
C42 C41 N5 120.8(3) . .
C46 C41 N5 119.2(2) . .
C41 C42 C43 119.3(3) . .
C41 C42 H42 120.4 . .
C43 C42 H42 120.4 . .
C44 C43 C42 121.1(3) . .
C44 C43 H43 119.4 . .
C42 C43 H43 119.4 . .
C43 C44 C45 119.7(3) . .
C43 C44 H44 120.1 . .
C45 C44 H44 120.1 . .
C46 C45 C44 120.1(3) . .
C46 C45 H45 120.0 . .
C44 C45 H45 120.0 . .
C45 C46 C41 119.8(3) . .
C45 C46 H46 120.1 . .
C41 C46 H46 120.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C16 1.301(3) .
N1 C17 1.385(3) .
C21 C22 1.379(4) .
C21 C21 1.412(6) 3_655
C21 C24 1.513(4) .
C24 N4 1.057(4) .
N5 C31 1.417(3) .
N5 C1 1.427(3) .
N5 C41 1.428(3) .
C1 C2 1.390(4) .
C1 C14 1.394(4) .
C2 C3 1.390(4) .
C2 H2 0.9500 .
C3 C12 1.403(4) .
C3 C11 1.527(4) 3_655
C11 C16 1.514(4) .
C11 C3 1.527(4) 3_655
C11 C12 1.530(3) .
C11 H11 1.0000 .
C12 C13 1.383(4) .
C13 C14 1.395(4) .
C13 H13 0.9500 .
C14 H14 0.9500 .
C16 C16 1.451(5) 3_655
C17 C17 1.402(6) 3_655
C17 C22 1.409(4) .
C22 H22 0.9500 .
C31 C36 1.392(4) .
C31 C32 1.398(4) .
C32 C33 1.372(4) .
C32 H32 0.9500 .
C33 C34 1.360(4) .
C33 H33 0.9500 .
C34 C35 1.380(4) .
C34 H34 0.9500 .
C35 C36 1.388(4) .
C35 H35 0.9500 .
C36 H36 0.9500 .
C41 C42 1.383(4) .
C41 C46 1.396(4) .
C42 C43 1.399(4) .
C42 H42 0.9500 .
C43 C44 1.353(4) .
C43 H43 0.9500 .
C44 C45 1.401(4) .
C44 H44 0.9500 .
C45 C46 1.378(4) .
C45 H45 0.9500 .
C46 H46 0.9500 .
