#------------------------------------------------------------------------------
#$Date: 2023-09-05 23:28:25 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286199 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/93/1569372.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_1569372
loop_
_publ_author_name
'Wu, Yimin'
'Liu, Xiaoyu'
'Liu, Junjie'
'Yang, Ge'
'Han, Songyan'
'Yang, Dezhi'
'Cao, Xiaosong'
'Ma, Dongge'
'Bin, Zhengyang'
'You, Jingsong'
_publ_section_title
;
 Geometry engineering of a multiple resonance core via a
 phenyl-embedded strategy toward highly efficient narrowband blue OLEDs.
;
_journal_issue                   9
_journal_name_full               'Materials horizons'
_journal_page_first              3785
_journal_page_last               3790
_journal_paper_doi               10.1039/d3mh00617d
_journal_volume                  10
_journal_year                    2023
_chemical_formula_moiety         'C26 H13 N O2'
_chemical_formula_sum            'C26 H13 N O2'
_chemical_formula_weight         371.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           31
_space_group_name_Hall           'P 2ac -2'
_space_group_name_H-M_alt        'P m n 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-03-16 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.208(4)
_cell_length_b                   4.0870(10)
_cell_length_c                   12.278(2)
_cell_measurement_reflns_used    1584
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.272
_cell_measurement_theta_min      2.513
_cell_volume                     813.3(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      200.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4870
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.521
_diffrn_reflns_theta_min         2.081
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0908 before and 0.0423 after correction.
The Ratio of minimum to maximum transmission is 0.8832.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_description       plate
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 519 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -3.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1841
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0448
_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)+(0.0395P)²+0.0918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_full    0.905
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                1479
_reflns_number_total             1841
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3mh00617d2.cif
_cod_data_source_block           mo_wym_hph4_0ma_a
_cod_depositor_comments
'Adding full bibliography for 1569367--1569372.cif.'
_cod_database_code               1569372
_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.
;
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.963
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y, z'
'x+1/2, -y, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.28577(15) 0.4606(7) 0.74696(19) 0.0391(7) Uani 1 1 d . . . . .
N1 N 0.5000 0.3644(9) 0.5652(3) 0.0214(8) Uani 1 2 d S T P . .
C1 C 0.5000 0.8724(12) 0.8672(4) 0.0336(12) Uani 1 2 d S T P . .
H1 H 0.5000 1.0119 0.9291 0.040 Uiso 1 2 calc R U P . .
C2 C 0.4271(2) 0.7680(9) 0.8209(3) 0.0315(8) Uani 1 1 d . . . . .
H2 H 0.3763 0.8214 0.8552 0.038 Uiso 1 1 calc R U . . .
C3 C 0.4262(2) 0.5861(8) 0.7249(2) 0.0249(7) Uani 1 1 d . . . . .
C4 C 0.5000 0.5120(10) 0.6689(3) 0.0229(10) Uani 1 2 d S T P . .
C5 C 0.42189(19) 0.2482(8) 0.5235(2) 0.0216(6) Uani 1 1 d . . . . .
C6 C 0.4084(2) 0.1452(8) 0.4142(3) 0.0245(7) Uani 1 1 d . . . . .
C7 C 0.4573(2) 0.2519(9) 0.3185(3) 0.0249(7) Uani 1 1 d . . . . .
C8 C 0.4148(2) 0.3545(9) 0.2252(3) 0.0310(8) Uani 1 1 d . . . . .
H8 H 0.3562 0.3570 0.2252 0.037 Uiso 1 1 calc R U . . .
C9 C 0.4576(2) 0.4529(9) 0.1326(3) 0.0360(9) Uani 1 1 d . . . . .
H9 H 0.4282 0.5200 0.0694 0.043 Uiso 1 1 calc R U . . .
C10 C 0.3491(2) 0.4316(8) 0.6926(2) 0.0276(8) Uani 1 1 d . . . . .
C11 C 0.3522(2) 0.2414(8) 0.5925(2) 0.0252(7) Uani 1 1 d . . . . .
C12 C 0.2803(2) 0.0749(8) 0.5633(3) 0.0297(8) Uani 1 1 d . . . . .
H12 H 0.2350 0.0697 0.6123 0.036 Uiso 1 1 calc R U . . .
C13 C 0.2741(2) -0.0803(9) 0.4652(3) 0.0315(8) Uani 1 1 d . . . . .
H13 H 0.2287 -0.2184 0.4488 0.038 Uiso 1 1 calc R U . . .
C14 C 0.3369(2) -0.0284(9) 0.3907(3) 0.0292(7) Uani 1 1 d . . . . .
H14 H 0.3307 -0.1163 0.3196 0.035 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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
C4 N1 C5 117.43(18) . 3_655 ?
C4 N1 C5 117.43(18) . . ?
C5 N1 C5 122.2(4) 3_655 . ?
C2 C1 H1 121.0 . . ?
C2 C1 H1 121.0 3_655 . ?
C2 C1 C2 117.9(5) 3_655 . ?
C1 C2 H2 119.2 . . ?
C1 C2 C3 121.5(3) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 C10 118.1(3) . . ?
C4 C3 C10 120.1(3) . . ?
N1 C4 C3 122.1(2) . 3_655 ?
N1 C4 C3 122.1(2) . . ?
C3 C4 C3 115.7(4) 3_655 . ?
C6 C5 N1 124.4(3) . . ?
C11 C5 N1 119.6(3) . . ?
C11 C5 C6 115.9(3) . . ?
C5 C6 C7 125.3(3) . . ?
C14 C6 C5 118.4(3) . . ?
C14 C6 C7 115.6(3) . . ?
C7 C7 C6 122.29(18) 3_655 . ?
C7 C7 C8 119.4(2) 3_655 . ?
C8 C7 C6 118.3(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.1 . . ?
C9 C9 C8 119.9(2) 3_655 . ?
C9 C9 H9 120.1 3_655 . ?
O1 C10 C3 121.8(3) . . ?
O1 C10 C11 122.6(3) . . ?
C3 C10 C11 115.6(3) . . ?
C5 C11 C10 121.6(3) . . ?
C12 C11 C5 121.5(3) . . ?
C12 C11 C10 116.6(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 121.4 . . ?
C12 C13 C14 117.3(3) . . ?
C14 C13 H13 121.4 . . ?
C6 C14 H14 118.2 . . ?
C13 C14 C6 123.7(3) . . ?
C13 C14 H14 118.2 . . ?
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
O1 C10 1.230(4) . ?
N1 C4 1.409(6) . ?
N1 C5 1.446(3) . ?
N1 C5 1.446(3) 3_655 ?
C1 H1 0.9500 . ?
C1 C2 1.379(4) 3_655 ?
C1 C2 1.379(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(4) . ?
C3 C4 1.413(4) . ?
C3 C10 1.455(5) . ?
C4 C3 1.413(4) 3_655 ?
C5 C6 1.423(4) . ?
C5 C11 1.412(4) . ?
C6 C7 1.483(4) . ?
C6 C14 1.389(5) . ?
C7 C7 1.386(6) 3_655 ?
C7 C8 1.400(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.391(5) . ?
C9 C9 1.375(8) 3_655 ?
C9 H9 0.9500 . ?
C10 C11 1.456(4) . ?
C11 C12 1.397(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.364(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(5) . ?
C14 H14 0.9500 . ?
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
O1 C10 C11 C5 171.0(3) . . . . ?
O1 C10 C11 C12 -3.5(5) . . . . ?
N1 C5 C6 C7 -24.8(5) . . . . ?
N1 C5 C6 C14 165.7(3) . . . . ?
N1 C5 C11 C10 18.2(5) . . . . ?
N1 C5 C11 C12 -167.5(3) . . . . ?
C1 C2 C3 C4 -2.5(5) . . . . ?
C1 C2 C3 C10 168.3(4) . . . . ?
C2 C1 C2 C3 -5.4(7) 3_655 . . . ?
C2 C3 C4 N1 -171.9(3) . . . . ?
C2 C3 C4 C3 9.9(6) . . . 3_655 ?
C2 C3 C10 O1 0.6(5) . . . . ?
C2 C3 C10 C11 -179.2(3) . . . . ?
C3 C10 C11 C5 -9.1(4) . . . . ?
C3 C10 C11 C12 176.3(3) . . . . ?
C4 N1 C5 C6 168.9(3) . . . . ?
C4 N1 C5 C11 -9.3(5) . . . . ?
C4 C3 C10 O1 171.4(3) . . . . ?
C4 C3 C10 C11 -8.4(4) . . . . ?
C5 N1 C4 C3 8.5(5) 3_655 . . 3_655 ?
C5 N1 C4 C3 169.6(3) . . . 3_655 ?
C5 N1 C4 C3 -8.5(5) . . . . ?
C5 N1 C4 C3 -169.6(3) 3_655 . . . ?
C5 N1 C5 C6 -31.0(6) 3_655 . . . ?
C5 N1 C5 C11 150.9(3) 3_655 . . . ?
C5 C6 C7 C7 47.9(4) . . . 3_655 ?
C5 C6 C7 C8 -132.4(3) . . . . ?
C5 C6 C14 C13 6.4(5) . . . . ?
C5 C11 C12 C13 -1.8(5) . . . . ?
C6 C5 C11 C10 -160.0(3) . . . . ?
C6 C5 C11 C12 14.2(4) . . . . ?
C6 C7 C8 C9 -179.1(3) . . . . ?
C7 C6 C14 C13 -164.1(3) . . . . ?
C7 C7 C8 C9 0.6(4) 3_655 . . . ?
C7 C8 C9 C9 -0.6(4) . . . 3_655 ?
C10 C3 C4 N1 17.5(5) . . . . ?
C10 C3 C4 C3 -160.6(2) . . . 3_655 ?
C10 C11 C12 C13 172.8(3) . . . . ?
C11 C5 C6 C7 153.3(3) . . . . ?
C11 C5 C6 C14 -16.2(4) . . . . ?
C11 C12 C13 C14 -8.7(5) . . . . ?
C12 C13 C14 C6 6.4(5) . . . . ?
C14 C6 C7 C7 -142.4(2) . . . 3_655 ?
C14 C6 C7 C8 37.4(5) . . . . ?
