#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/64/7236482.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_7236482
loop_
_publ_author_name
'Li, Chenglong'
'Li, Zhiqiang'
'Yan, Xianju'
'Zhang, Yuewei'
'Zhang, Zuolun'
'Wang, Yue'
_publ_section_title
;
 Structurally simple non-doped sky-blue OLEDs with high luminance and
 efficiencies at low driving voltages
;
_journal_issue                   8
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              1973
_journal_paper_doi               10.1039/C6TC05639C
_journal_volume                  5
_journal_year                    2017
_chemical_formula_moiety         'C53 H33 N3'
_chemical_formula_sum            'C53 H33 N3'
_chemical_formula_weight         711.82
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-12-01 deposited with the CCDC.
2017-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                94.64(3)
_cell_angle_beta                 102.84(3)
_cell_angle_gamma                106.29(3)
_cell_formula_units_Z            2
_cell_length_a                   9.0678(18)
_cell_length_b                   13.681(3)
_cell_length_c                   16.569(3)
_cell_measurement_reflns_used    9684
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.775
_cell_measurement_theta_min      3.01
_cell_volume                     1901.0(8)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_unetI/netI     0.0936
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18119
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.012
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.072
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         8467
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1744
_refine_ls_R_factor_gt           0.0753
_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)+(0.1032P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1752
_refine_ls_wR_factor_ref         0.2337
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3624
_reflns_number_total             8467
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6tc05639c2.cif
_cod_data_source_block           1
_cod_original_cell_volume        1901.1(7)
_cod_database_code               7236482
_shelx_shelxl_version_number     2014/7
_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'
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
C1 C 0.9107(4) 0.9209(2) 0.23047(19) 0.0475(8) Uani 1 1 d . .
C2 C 1.0806(4) 0.8116(2) 0.25962(19) 0.0466(8) Uani 1 1 d . .
C3 C 0.9418(4) 0.7233(2) 0.24548(19) 0.0474(8) Uani 1 1 d . .
C4 C 1.3777(4) 1.1184(2) 0.2266(2) 0.0486(8) Uani 1 1 d . .
C5 C 0.7722(4) 0.8327(2) 0.21675(19) 0.0460(7) Uani 1 1 d . .
N2 N 1.2517(3) 1.03119(19) 0.19399(16) 0.0509(7) Uani 1 1 d . .
C7 C 1.0622(4) 0.9091(2) 0.25222(19) 0.0468(8) Uani 1 1 d . .
C8 C 0.6465(4) 0.6419(2) 0.2052(2) 0.0494(8) Uani 1 1 d . .
N1 N 1.2921(3) 1.06159(18) 0.33304(15) 0.0487(7) Uani 1 1 d . .
C10 C 1.4720(4) 1.1823(2) 0.1809(2) 0.0520(9) Uani 1 1 d . .
C11 C 0.7906(4) 0.7349(2) 0.22435(19) 0.0474(8) Uani 1 1 d . .
C12 C 1.2026(4) 0.9991(2) 0.2590(2) 0.0476(8) Uani 1 1 d . .
C13 C 0.3591(4) 0.4512(2) 0.29657(19) 0.0483(8) Uani 1 1 d . .
C14 C 0.2279(4) 0.3796(2) 0.2403(2) 0.0518(8) Uani 1 1 d . .
N3 N 0.2392(3) 0.39037(19) 0.15901(16) 0.0551(8) Uani 1 1 d . .
C16 C 1.4064(4) 1.1399(2) 0.3119(2) 0.0486(8) Uani 1 1 d . .
C17 C 0.5901(4) 0.5956(2) 0.2679(2) 0.0493(8) Uani 1 1 d . .
H17A H 0.6440 0.6211 0.3236 0.059 Uiso 1 1 calc R U
C18 C 0.3740(4) 0.4720(2) 0.1628(2) 0.0505(8) Uani 1 1 d . .
C19 C 0.4535(4) 0.5113(2) 0.24852(19) 0.0464(8) Uani 1 1 d . .
C20 C 0.8900(4) 1.0196(2) 0.2211(2) 0.0624(10) Uani 1 1 d . .
H20A H 0.9785 1.0774 0.2300 0.075 Uiso 1 1 calc R U
C21 C 1.5970(4) 1.2696(2) 0.2272(2) 0.0586(9) Uani 1 1 d . .
C22 C 0.9674(4) 0.6254(2) 0.2516(2) 0.0645(10) Uani 1 1 d . .
H22A H 0.8797 0.5671 0.2431 0.077 Uiso 1 1 calc R U
C23 C 0.6219(4) 0.8490(3) 0.1949(2) 0.0583(9) Uani 1 1 d . .
H23A H 0.5310 0.7927 0.1857 0.070 Uiso 1 1 calc R U
C24 C 0.5670(4) 0.6004(3) 0.1216(2) 0.0591(10) Uani 1 1 d . .
H24A H 0.6064 0.6311 0.0795 0.071 Uiso 1 1 calc R U
C25 C 1.2330(4) 0.7955(3) 0.2778(2) 0.0573(9) Uani 1 1 d . .
H25A H 1.3237 0.8519 0.2868 0.069 Uiso 1 1 calc R U
C26 C 0.4327(4) 0.5161(3) 0.0994(2) 0.0607(10) Uani 1 1 d . .
H26A H 0.3827 0.4894 0.0434 0.073 Uiso 1 1 calc R U
C27 C 0.6054(5) 0.9432(3) 0.1869(3) 0.0714(11) Uani 1 1 d . .
H27A H 0.5047 0.9511 0.1732 0.086 Uiso 1 1 calc R U
C28 C 1.6265(4) 1.2916(2) 0.3177(2) 0.0583(9) Uani 1 1 d . .
C29 C 1.5330(4) 1.2254(2) 0.3618(2) 0.0531(9) Uani 1 1 d . .
C30 C 0.3692(4) 0.4572(3) 0.3822(2) 0.0633(10) Uani 1 1 d . .
H30A H 0.4571 0.5029 0.4208 0.076 Uiso 1 1 calc R U
C31 C 1.2612(4) 1.0526(2) 0.4144(2) 0.0532(9) Uani 1 1 d . .
C32 C 1.2490(4) 0.7011(3) 0.2821(2) 0.0686(11) Uani 1 1 d . .
H32A H 1.3496 0.6929 0.2937 0.082 Uiso 1 1 calc R U
C33 C 0.1037(4) 0.3174(2) 0.2670(2) 0.0611(10) Uani 1 1 d . .
H33A H 0.0156 0.2710 0.2290 0.073 Uiso 1 1 calc R U
C34 C 1.1124(5) 0.6144(3) 0.2689(3) 0.0737(12) Uani 1 1 d . .
H34A H 1.1237 0.5493 0.2723 0.088 Uiso 1 1 calc R U
C35 C 0.1267(4) 0.3300(3) 0.0850(2) 0.0587(9) Uani 1 1 d . .
C36 C 1.4456(5) 1.1592(3) 0.0937(2) 0.0719(11) Uani 1 1 d . .
H36A H 1.3639 1.1013 0.0640 0.086 Uiso 1 1 calc R U
C37 C 0.7419(5) 1.0292(3) 0.1995(3) 0.0775(12) Uani 1 1 d . .
H37A H 0.7302 1.0937 0.1928 0.093 Uiso 1 1 calc R U
C38 C 1.2950(5) 0.9767(3) 0.4574(2) 0.0707(11) Uani 1 1 d . .
H38A H 1.3329 0.9281 0.4334 0.085 Uiso 1 1 calc R U
C39 C 1.5717(5) 1.2469(3) 0.4496(2) 0.0755(12) Uani 1 1 d . .
H39A H 1.5124 1.2033 0.4790 0.091 Uiso 1 1 calc R U
C40 C 0.0839(5) 0.2227(3) 0.0770(3) 0.0812(12) Uani 1 1 d . .
H40A H 0.1315 0.1906 0.1180 0.097 Uiso 1 1 calc R U
C41 C 0.1160(5) 0.3271(3) 0.3515(3) 0.0712(11) Uani 1 1 d . .
H41A H 0.0335 0.2871 0.3707 0.085 Uiso 1 1 calc R U
C42 C 1.7507(5) 1.3778(3) 0.3646(3) 0.0821(13) Uani 1 1 d . .
H42A H 1.8121 1.4225 0.3368 0.099 Uiso 1 1 calc R U
C43 C 0.2463(5) 0.3942(3) 0.4087(3) 0.0737(11) Uani 1 1 d . .
H43A H 0.2520 0.3972 0.4656 0.088 Uiso 1 1 calc R U
C44 C 1.6905(5) 1.3309(3) 0.1810(3) 0.0825(13) Uani 1 1 d . .
H44A H 1.7742 1.3888 0.2090 0.099 Uiso 1 1 calc R U
C45 C 0.0551(5) 0.3762(3) 0.0245(2) 0.0780(13) Uani 1 1 d . .
H45A H 0.0818 0.4476 0.0304 0.094 Uiso 1 1 calc R U
C46 C 1.1986(6) 1.1210(3) 0.4481(3) 0.0837(13) Uani 1 1 d . .
H46A H 1.1704 1.1701 0.4176 0.100 Uiso 1 1 calc R U
C47 C -0.0582(6) 0.3157(4) -0.0460(3) 0.1040(18) Uani 1 1 d . .
H47A H -0.1041 0.3468 -0.0883 0.125 Uiso 1 1 calc R U
C48 C 1.6599(7) 1.3066(4) 0.0963(4) 0.1046(17) Uani 1 1 d . .
H48A H 1.7227 1.3492 0.0677 0.126 Uiso 1 1 calc R U
C49 C 1.6952(6) 1.3309(3) 0.4928(3) 0.0956(15) Uani 1 1 d . .
H49A H 1.7203 1.3436 0.5510 0.115 Uiso 1 1 calc R U
C50 C 1.7831(5) 1.3971(3) 0.4490(4) 0.0988(16) Uani 1 1 d . .
H50A H 1.8649 1.4553 0.4781 0.119 Uiso 1 1 calc R U
C51 C 1.5404(6) 1.2220(4) 0.0522(3) 0.0966(16) Uani 1 1 d . .
H51A H 1.5229 1.2068 -0.0055 0.116 Uiso 1 1 calc R U
C52 C 1.2144(6) 1.0422(4) 0.5719(3) 0.0928(15) Uani 1 1 d . .
H52A H 1.1999 1.0389 0.6255 0.111 Uiso 1 1 calc R U
C53 C -0.1019(6) 0.2109(5) -0.0532(3) 0.1074(19) Uani 1 1 d . .
H53A H -0.1807 0.1706 -0.0993 0.129 Uiso 1 1 calc R U
C54 C -0.0300(6) 0.1657(4) 0.0072(4) 0.1022(17) Uani 1 1 d . .
H54A H -0.0587 0.0942 0.0010 0.123 Uiso 1 1 calc R U
C55 C 1.2718(6) 0.9734(4) 0.5367(3) 0.0936(15) Uani 1 1 d . .
H55A H 1.2963 0.9228 0.5665 0.112 Uiso 1 1 calc R U
C56 C 1.1774(6) 1.1166(4) 0.5286(3) 0.1021(16) Uani 1 1 d . .
H56A H 1.1381 1.1642 0.5528 0.122 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
C7 C1 C20 121.3(3)
C7 C1 C5 119.9(3)
C20 C1 C5 118.8(3)
C7 C2 C25 122.4(3)
C7 C2 C3 119.3(3)
C25 C2 C3 118.2(3)
C11 C3 C22 122.9(3)
C11 C3 C2 120.1(3)
C22 C3 C2 116.9(3)
N2 C4 C16 111.6(3)
N2 C4 C10 126.7(3)
C16 C4 C10 121.8(3)
C11 C5 C23 123.0(3)
C11 C5 C1 119.5(3)
C23 C5 C1 117.5(3)
C12 N2 C4 105.0(3)
C1 C7 C2 120.7(3)
C1 C7 C12 119.1(3)
C2 C7 C12 120.0(3)
C17 C8 C24 119.0(3)
C17 C8 C11 121.7(3)
C24 C8 C11 119.4(3)
C12 N1 C16 106.2(2)
C12 N1 C31 126.0(2)
C16 N1 C31 127.5(3)
C36 C10 C21 120.6(3)
C36 C10 C4 122.0(3)
C21 C10 C4 117.4(3)
C3 C11 C5 120.5(3)
C3 C11 C8 119.8(3)
C5 C11 C8 119.6(3)
N2 C12 N1 112.3(2)
N2 C12 C7 123.5(3)
N1 C12 C7 124.1(3)
C30 C13 C14 119.1(3)
C30 C13 C19 133.1(3)
C14 C13 C19 107.6(3)
C33 C14 N3 128.8(3)
C33 C14 C13 121.8(3)
N3 C14 C13 109.1(3)
C14 N3 C18 108.3(2)
C14 N3 C35 125.1(3)
C18 N3 C35 126.6(3)
C4 C16 N1 104.9(3)
C4 C16 C29 123.1(3)
N1 C16 C29 131.9(3)
C8 C17 C19 120.6(3)
C26 C18 N3 130.6(3)
C26 C18 C19 120.7(3)
N3 C18 C19 108.7(3)
C17 C19 C18 119.0(3)
C17 C19 C13 134.7(3)
C18 C19 C13 106.2(3)
C37 C20 C1 120.4(3)
C44 C21 C10 116.5(4)
C44 C21 C28 123.1(4)
C10 C21 C28 120.4(3)
C34 C22 C3 122.6(3)
C27 C23 C5 122.6(3)
C26 C24 C8 122.5(3)
C32 C25 C2 121.9(3)
C24 C26 C18 118.1(3)
C23 C27 C37 119.5(4)
C42 C28 C29 118.0(4)
C42 C28 C21 121.0(3)
C29 C28 C21 121.0(3)
C39 C29 C28 118.8(3)
C39 C29 C16 124.9(3)
C28 C29 C16 116.3(3)
C43 C30 C13 119.0(3)
C46 C31 C38 120.4(3)
C46 C31 N1 119.1(3)
C38 C31 N1 120.5(3)
C25 C32 C34 119.8(4)
C41 C33 C14 117.5(3)
C22 C34 C32 120.5(3)
C45 C35 C40 120.2(3)
C45 C35 N3 120.5(3)
C40 C35 N3 119.1(3)
C51 C36 C10 120.2(4)
C20 C37 C27 121.1(3)
C31 C38 C55 119.1(4)
C49 C39 C29 121.3(4)
C54 C40 C35 118.4(4)
C33 C41 C43 122.1(3)
C50 C42 C28 121.6(4)
C41 C43 C30 120.5(4)
C48 C44 C21 121.1(4)
C35 C45 C47 119.6(4)
C31 C46 C56 119.3(4)
C53 C47 C45 120.2(5)
C44 C48 C51 122.1(4)
C39 C49 C50 119.5(4)
C42 C50 C49 120.8(4)
C48 C51 C36 119.5(5)
C55 C52 C56 119.9(4)
C54 C53 C47 119.6(4)
C53 C54 C40 121.9(5)
C52 C55 C38 121.2(4)
C52 C56 C46 119.9(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C7 1.399(4)
C1 C20 1.429(4)
C1 C5 1.437(4)
C2 C7 1.402(4)
C2 C25 1.430(5)
C2 C3 1.439(4)
C3 C11 1.395(4)
C3 C22 1.429(4)
C4 N2 1.370(4)
C4 C16 1.372(4)
C4 C10 1.430(4)
C5 C11 1.406(4)
C5 C23 1.415(5)
N2 C12 1.316(4)
C7 C12 1.478(4)
C8 C17 1.379(4)
C8 C24 1.399(5)
C8 C11 1.498(4)
N1 C12 1.376(4)
N1 C16 1.394(4)
N1 C31 1.445(4)
C10 C36 1.405(5)
C10 C21 1.416(5)
C13 C30 1.395(5)
C13 C14 1.396(4)
C13 C19 1.434(4)
C14 C33 1.390(4)
C14 N3 1.390(4)
N3 C18 1.390(4)
N3 C35 1.427(4)
C16 C29 1.427(4)
C17 C19 1.389(4)
C18 C26 1.386(4)
C18 C19 1.425(4)
C20 C37 1.358(5)
C21 C44 1.415(5)
C21 C28 1.454(5)
C22 C34 1.335(5)
C23 C27 1.352(5)
C24 C26 1.377(4)
C25 C32 1.345(5)
C27 C37 1.411(5)
C28 C42 1.407(5)
C28 C29 1.423(4)
C29 C39 1.405(5)
C30 C43 1.385(5)
C31 C46 1.366(5)
C31 C38 1.372(5)
C32 C34 1.415(5)
C33 C41 1.373(5)
C35 C45 1.367(5)
C35 C40 1.396(5)
C36 C51 1.377(5)
C38 C55 1.378(5)
C39 C49 1.369(5)
C40 C54 1.373(6)
C41 C43 1.374(5)
C42 C50 1.351(6)
C44 C48 1.363(7)
C45 C47 1.392(6)
C46 C56 1.393(6)
C47 C53 1.363(7)
C48 C51 1.363(7)
C49 C50 1.394(6)
C52 C55 1.348(6)
C52 C56 1.366(6)
C53 C54 1.359(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339722
