#------------------------------------------------------------------------------
#$Date: 2019-11-24 10:58:03 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237715 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/74/7237496.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_7237496
loop_
_publ_author_name
'Bian, Mengying'
'Wang, Yuanxun'
'Guo, Xuan'
'Lv, Fang'
'Chen, Zhijian'
'Duan, Lian'
'Bian, Zuqiang'
'Liu, Zhiwei'
'Geng, Hua'
'Xiao, Lixin'
_publ_section_title
;
 Positional isomerism effect of spirobifluorene and terpyridine moieties
 of “(A)n--D--(A)n” type electron transport materials for
 long-lived and highly efficient TADF-PhOLEDs
;
_journal_issue                   38
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              10276
_journal_paper_doi               10.1039/C8TC03796E
_journal_volume                  6
_journal_year                    2018
_chemical_formula_sum            'C57 H38 Cl4 N6'
_chemical_formula_weight         948.73
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-07-31 deposited with the CCDC.
2018-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 129.729(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.5621(10)
_cell_length_b                   24.2721(18)
_cell_length_c                   12.7702(7)
_cell_measurement_reflns_used    3840
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      27.9780
_cell_measurement_theta_min      2.6710
_cell_volume                     4663.3(6)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      179.99(10)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12016
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        23.253
_diffrn_reflns_theta_max         23.253
_diffrn_reflns_theta_min         2.668
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       sheet-like
_exptl_crystal_F_000             1960
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.457
_refine_diff_density_min         -1.147
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         3351
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1371
_refine_ls_R_factor_gt           0.1018
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0500P)²+60.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2208
_refine_ls_wR_factor_ref         0.2426
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2366
_reflns_number_total             3351
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8tc03796e2.cif
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7237496
_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+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'
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
N17 N 0.6061(3) 0.27071(19) 0.7502(5) 0.0316(11) Uani 1 1 d . . .
N26 N 0.7086(3) 0.1467(2) 0.9479(5) 0.0450(13) Uani 1 1 d . . .
N32 N 0.5624(3) 0.3889(2) 0.5444(6) 0.0475(14) Uani 1 1 d . . .
C1 C 1.0000 0.3231(3) 0.7500 0.0262(17) Uani 1 2 d S T P
C2 C 1.0459(3) 0.3630(2) 0.8704(6) 0.0314(13) Uani 1 1 d . . .
C3 C 1.0280(4) 0.4174(2) 0.8243(6) 0.0404(15) Uani 1 1 d . . .
C4 C 1.0615(5) 0.4594(3) 0.9159(7) 0.060(2) Uani 1 1 d . . .
H4 H 1.0495 0.4958 0.8861 0.073 Uiso 1 1 calc R U .
C5 C 1.1137(5) 0.4477(3) 1.0542(8) 0.065(2) Uani 1 1 d . . .
H5 H 1.1359 0.4764 1.1164 0.078 Uiso 1 1 calc R U .
C6 C 1.1326(4) 0.3944(3) 1.0996(7) 0.0461(16) Uani 1 1 d . . .
H6 H 1.1681 0.3871 1.1923 0.055 Uiso 1 1 calc R U .
C7 C 1.0986(4) 0.3512(2) 1.0069(6) 0.0352(14) Uani 1 1 d . . .
H7 H 1.1115 0.3149 1.0370 0.042 Uiso 1 1 calc R U .
C8 C 0.9364(3) 0.2832(2) 0.7423(5) 0.0275(12) Uani 1 1 d . . .
C9 C 0.9605(3) 0.2290(2) 0.7450(6) 0.0304(13) Uani 1 1 d . . .
C10 C 0.9129(4) 0.1854(2) 0.7393(6) 0.0370(14) Uani 1 1 d . . .
H10 H 0.9280 0.1492 0.7379 0.044 Uiso 1 1 calc R U .
C11 C 0.8425(4) 0.1967(2) 0.7359(6) 0.0377(14) Uani 1 1 d . . .
H11 H 0.8106 0.1677 0.7336 0.045 Uiso 1 1 calc R U .
C12 C 0.8179(3) 0.2506(2) 0.7357(6) 0.0314(13) Uani 1 1 d . . .
C13 C 0.8646(3) 0.2942(2) 0.7367(5) 0.0300(13) Uani 1 1 d . . .
H13 H 0.8478 0.3304 0.7337 0.036 Uiso 1 1 calc R U .
C14 C 0.7453(3) 0.2594(2) 0.7419(6) 0.0295(13) Uani 1 1 d . . .
C15 C 0.6833(3) 0.3013(2) 0.6711(6) 0.0335(14) Uani 1 1 d . . .
H15 H 0.6869 0.3261 0.6191 0.040 Uiso 1 1 calc R U .
C16 C 0.6152(3) 0.3060(2) 0.6787(6) 0.0321(13) Uani 1 1 d . . .
C18 C 0.6661(3) 0.2302(2) 0.8193(5) 0.0303(13) Uani 1 1 d . . .
C19 C 0.7371(3) 0.2242(2) 0.8188(5) 0.0310(13) Uani 1 1 d . . .
H19 H 0.7789 0.1965 0.8701 0.037 Uiso 1 1 calc R U .
C21 C 0.6541(3) 0.1901(2) 0.8939(6) 0.0318(13) Uani 1 1 d . . .
C22 C 0.5887(4) 0.1972(2) 0.9056(6) 0.0351(14) Uani 1 1 d . . .
H22 H 0.5530 0.2285 0.8706 0.042 Uiso 1 1 calc R U .
C23 C 0.5778(4) 0.1573(3) 0.9697(6) 0.0418(16) Uani 1 1 d . . .
H23 H 0.5330 0.1606 0.9755 0.050 Uiso 1 1 calc R U .
C24 C 0.6324(4) 0.1130(3) 1.0246(7) 0.0477(17) Uani 1 1 d . . .
H24 H 0.6265 0.0857 1.0694 0.057 Uiso 1 1 calc R U .
C25 C 0.6972(5) 0.1097(3) 1.0120(8) 0.0562(19) Uani 1 1 d . . .
H25 H 0.7353 0.0796 1.0508 0.067 Uiso 1 1 calc R U .
C27 C 0.5472(4) 0.3502(2) 0.6018(6) 0.0356(14) Uani 1 1 d . . .
C28 C 0.4720(4) 0.3508(3) 0.5913(6) 0.0410(15) Uani 1 1 d . . .
H28 H 0.4634 0.3235 0.6330 0.049 Uiso 1 1 calc R U .
C29 C 0.4106(4) 0.3920(3) 0.5185(7) 0.0463(17) Uani 1 1 d . . .
H29 H 0.3599 0.3931 0.5104 0.056 Uiso 1 1 calc R U .
C30 C 0.4252(4) 0.4313(3) 0.4583(7) 0.0517(18) Uani 1 1 d . . .
H30 H 0.3844 0.4595 0.4079 0.062 Uiso 1 1 calc R U .
C31 C 0.5018(4) 0.4282(3) 0.4737(8) 0.057(2) Uani 1 1 d . . .
H31 H 0.5113 0.4551 0.4324 0.068 Uiso 1 1 calc R U .
Cl1 Cl 0.8557(3) 0.02326(17) 0.6376(4) 0.1470(14) Uani 1 1 d D . .
Cl2 Cl 0.7293(3) 0.03456(19) 0.3531(3) 0.177(2) Uani 1 1 d D . .
C33 C 0.7868(7) 0.0655(4) 0.4997(9) 0.102(3) Uani 1 1 d D . .
H33A H 0.7460 0.0834 0.5078 0.122 Uiso 1 1 calc R U .
H33B H 0.8224 0.0940 0.5019 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'
Cl Cl 0.1484 0.1585 '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
C18 N17 C16 118.3(4) . .
C21 N26 C25 117.3(5) . .
C31 N32 C27 117.4(5) . .
C8 C1 C8 101.4(6) 2_756 .
C8 C1 C2 113.3(3) 2_756 2_756
C8 C1 C2 113.9(3) . 2_756
C8 C1 C2 113.9(3) 2_756 .
C8 C1 C2 113.3(3) . .
C2 C1 C2 101.5(6) 2_756 .
C7 C2 C3 120.9(5) . .
C7 C2 C1 128.8(5) . .
C3 C2 C1 110.3(5) . .
C4 C3 C2 119.5(6) . .
C4 C3 C3 131.6(4) . 2_756
C2 C3 C3 108.9(3) . 2_756
C3 C4 C5 119.8(7) . .
C3 C4 H4 120.1 . .
C5 C4 H4 120.1 . .
C4 C5 C6 120.7(7) . .
C4 C5 H5 119.6 . .
C6 C5 H5 119.6 . .
C7 C6 C5 120.0(6) . .
C7 C6 H6 120.0 . .
C5 C6 H6 120.0 . .
C2 C7 C6 119.1(6) . .
C2 C7 H7 120.4 . .
C6 C7 H7 120.4 . .
C13 C8 C9 120.1(5) . .
C13 C8 C1 129.5(5) . .
C9 C8 C1 110.4(4) . .
C10 C9 C8 121.1(5) . .
C10 C9 C9 130.0(3) . 2_756
C8 C9 C9 108.9(3) . 2_756
C11 C10 C9 118.4(5) . .
C11 C10 H10 120.8 . .
C9 C10 H10 120.8 . .
C10 C11 C12 121.7(5) . .
C10 C11 H11 119.1 . .
C12 C11 H11 119.1 . .
C11 C12 C13 119.3(5) . .
C11 C12 C14 118.4(5) . .
C13 C12 C14 122.2(5) . .
C8 C13 C12 119.3(5) . .
C8 C13 H13 120.3 . .
C12 C13 H13 120.3 . .
C19 C14 C15 117.8(5) . .
C19 C14 C12 119.6(5) . .
C15 C14 C12 122.6(5) . .
C14 C15 C16 119.2(5) . .
C14 C15 H15 120.4 . .
C16 C15 H15 120.4 . .
N17 C16 C15 122.8(5) . .
N17 C16 C27 117.1(5) . .
C15 C16 C27 120.1(5) . .
N17 C18 C19 121.7(5) . .
N17 C18 C21 118.2(5) . .
C19 C18 C21 120.0(5) . .
C14 C19 C18 120.2(5) . .
C14 C19 H19 119.9 . .
C18 C19 H19 119.9 . .
N26 C21 C22 121.9(5) . .
N26 C21 C18 116.6(5) . .
C22 C21 C18 121.5(5) . .
C23 C22 C21 118.8(6) . .
C23 C22 H22 120.6 . .
C21 C22 H22 120.6 . .
C24 C23 C22 119.9(6) . .
C24 C23 H23 120.1 . .
C22 C23 H23 120.1 . .
C23 C24 C25 117.8(6) . .
C23 C24 H24 121.1 . .
C25 C24 H24 121.1 . .
N26 C25 C24 124.2(6) . .
N26 C25 H25 117.9 . .
C24 C25 H25 117.9 . .
N32 C27 C28 122.3(5) . .
N32 C27 C16 116.6(5) . .
C28 C27 C16 121.1(5) . .
C29 C28 C27 119.2(6) . .
C29 C28 H28 120.4 . .
C27 C28 H28 120.4 . .
C28 C29 C30 118.9(6) . .
C28 C29 H29 120.5 . .
C30 C29 H29 120.5 . .
C29 C30 C31 118.7(6) . .
C29 C30 H30 120.7 . .
C31 C30 H30 120.7 . .
N32 C31 C30 123.5(6) . .
N32 C31 H31 118.3 . .
C30 C31 H31 118.3 . .
Cl2 C33 Cl1 114.7(6) . .
Cl2 C33 H33A 108.6 . .
Cl1 C33 H33A 108.6 . .
Cl2 C33 H33B 108.6 . .
Cl1 C33 H33B 108.6 . .
H33A C33 H33B 107.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N17 C18 1.341(7) .
N17 C16 1.344(7) .
N26 C21 1.335(7) .
N26 C25 1.327(8) .
N32 C31 1.328(8) .
N32 C27 1.338(7) .
C1 C8 1.530(7) 2_756
C1 C8 1.530(7) .
C1 C2 1.531(7) 2_756
C1 C2 1.531(7) .
C2 C7 1.373(8) .
C2 C3 1.397(8) .
C3 C4 1.363(9) .
C3 C3 1.464(12) 2_756
C4 C5 1.392(10) .
C4 H4 0.9300 .
C5 C6 1.368(10) .
C5 H5 0.9300 .
C6 C7 1.391(8) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C8 C13 1.385(7) .
C8 C9 1.389(8) .
C9 C10 1.382(8) .
C9 C9 1.467(10) 2_756
C10 C11 1.376(8) .
C10 H10 0.9300 .
C11 C12 1.393(8) .
C11 H11 0.9300 .
C12 C13 1.394(8) .
C12 C14 1.488(7) .
C13 H13 0.9300 .
C14 C19 1.386(8) .
C14 C15 1.386(8) .
C15 C16 1.401(7) .
C15 H15 0.9300 .
C16 C27 1.490(8) .
C18 C19 1.402(7) .
C18 C21 1.482(8) .
C19 H19 0.9300 .
C21 C22 1.389(7) .
C22 C23 1.370(8) .
C22 H22 0.9300 .
C23 C24 1.352(9) .
C23 H23 0.9300 .
C24 C25 1.378(9) .
C24 H24 0.9300 .
C25 H25 0.9300 .
C27 C28 1.387(8) .
C28 C29 1.371(8) .
C28 H28 0.9300 .
C29 C30 1.365(9) .
C29 H29 0.9300 .
C30 C31 1.382(9) .
C30 H30 0.9300 .
C31 H31 0.9300 .
Cl1 C33 1.713(10) .
Cl2 C33 1.625(9) .
C33 H33A 0.9700 .
C33 H33B 0.9700 .
