#------------------------------------------------------------------------------
#$Date: 2023-09-05 23:28:25 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286199 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/93/1569370.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_1569370
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         'C30 H23 N O4'
_chemical_formula_sum            'C30 H23 N O4'
_chemical_formula_weight         461.49
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-03-17 deposited with the CCDC.	2023-06-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 120.406(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7721(8)
_cell_length_b                   14.0494(8)
_cell_length_c                   12.9393(7)
_cell_measurement_reflns_used    6657
_cell_measurement_temperature    197(2)
_cell_measurement_theta_max      27.178
_cell_measurement_theta_min      2.244
_cell_volume                     2316.1(2)
_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      197.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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  0.0638
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27302
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.521
_diffrn_reflns_theta_min         2.158
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1080 before and 0.0595 after correction.
The Ratio of minimum to maximum transmission is 0.8993.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0392
_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)+(0.0469P)²+0.9397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1024
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2015
_reflns_number_total             2655
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3mh00617d2.cif
_cod_data_source_block           mo_wym_5563_0ma_a
_cod_depositor_comments
'Adding full bibliography for 1569367--1569372.cif.'
_cod_database_code               1569370
_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   0.982
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15),
 C16(H16)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.36808(7) 0.59986(7) 0.84391(8) 0.0341(2) Uani 1 1 d . . . . .
O2 O 0.40696(8) 0.75004(7) 0.82230(9) 0.0439(3) Uani 1 1 d . . . . .
N1 N 0.5000 0.50908(10) 0.7500 0.0240(3) Uani 1 2 d S T P . .
C1 C 0.90008(11) 0.49188(11) 1.03631(14) 0.0428(4) Uani 1 1 d . . . . .
H1 H 0.9725 0.4757 1.0785 0.051 Uiso 1 1 calc R U . . .
C2 C 0.86365(11) 0.56073(11) 1.07936(12) 0.0395(3) Uani 1 1 d . . . . .
H2 H 0.9113 0.5933 1.1509 0.047 Uiso 1 1 calc R U . . .
C3 C 0.75549(10) 0.58493(9) 1.01928(11) 0.0307(3) Uani 1 1 d . . . . .
C4 C 0.68394(9) 0.53502(8) 0.91290(10) 0.0261(3) Uani 1 1 d . . . . .
C5 C 0.57429(9) 0.55959(8) 0.85435(10) 0.0235(3) Uani 1 1 d . . . . .
C6 C 0.26192(11) 0.63035(12) 0.80650(14) 0.0471(4) Uani 1 1 d . . . . .
H6A H 0.2272 0.6519 0.7231 0.071 Uiso 1 1 calc R U . . .
H6B H 0.2643 0.6827 0.8578 0.071 Uiso 1 1 calc R U . . .
H6C H 0.2226 0.5769 0.8134 0.071 Uiso 1 1 calc R U . . .
C7 C 0.43254(10) 0.66800(9) 0.84765(10) 0.0278(3) Uani 1 1 d . . . . .
C8 C 0.54311(9) 0.63427(8) 0.89841(10) 0.0255(3) Uani 1 1 d . . . . .
C9 C 0.61709(10) 0.68634(9) 0.99999(11) 0.0320(3) Uani 1 1 d . . . . .
H9 H 0.5947 0.7401 1.0257 0.038 Uiso 1 1 calc R U . . .
C10 C 0.71947(10) 0.66028(10) 1.06092(11) 0.0353(3) Uani 1 1 d . . . . .
H10 H 0.7673 0.6931 1.1322 0.042 Uiso 1 1 calc R U . . .
C11 C 0.72583(10) 0.46533(9) 0.86904(12) 0.0331(3) Uani 1 1 d . . . . .
H11 H 0.6802 0.4327 0.7967 0.040 Uiso 1 1 calc R U . . .
C12 C 0.83061(11) 0.44441(10) 0.92904(13) 0.0402(3) Uani 1 1 d . . . . .
H12 H 0.8568 0.3974 0.8981 0.048 Uiso 1 1 calc R U . . .
C13 C 0.5000 0.40806(12) 0.7500 0.0255(4) Uani 1 2 d S T P . .
C14 C 0.53194(10) 0.35792(9) 0.85565(11) 0.0310(3) Uani 1 1 d . . . . .
H14 H 0.5527 0.3914 0.9281 0.037 Uiso 1 1 calc R U . . .
C15 C 0.53355(12) 0.25941(9) 0.85552(12) 0.0373(3) Uani 1 1 d . . . . .
H15 H 0.5579 0.2257 0.9285 0.045 Uiso 1 1 calc R U . . .
C16 C 0.5000 0.20970(14) 0.7500 0.0392(5) Uani 1 2 d S T P . .
H16 H 0.5000 0.1421 0.7500 0.047 Uiso 1 2 calc R U P . .
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
C7 O1 C6 115.53(11) . . ?
C5 N1 C5 120.27(13) 2_656 . ?
C13 N1 C5 119.86(7) . . ?
C13 N1 C5 119.86(7) . 2_656 ?
C2 C1 H1 120.0 . . ?
C2 C1 C12 120.00(13) . . ?
C12 C1 H1 120.0 . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.10(13) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 C4 119.34(12) . . ?
C10 C3 C2 120.59(12) . . ?
C10 C3 C4 120.01(12) . . ?
C3 C4 C5 118.49(11) . . ?
C11 C4 C3 117.70(12) . . ?
C11 C4 C5 123.79(11) . . ?
N1 C5 C4 120.05(10) . . ?
C8 C5 N1 120.80(10) . . ?
C8 C5 C4 119.12(10) . . ?
O1 C6 H6A 109.5 . . ?
O1 C6 H6B 109.5 . . ?
O1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 C8 112.91(10) . . ?
O2 C7 O1 123.82(12) . . ?
O2 C7 C8 122.99(12) . . ?
C5 C8 C7 125.32(10) . . ?
C5 C8 C9 120.96(11) . . ?
C9 C8 C7 113.72(11) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.70(12) . . ?
C10 C9 H9 119.6 . . ?
C3 C10 H10 119.8 . . ?
C9 C10 C3 120.46(12) . . ?
C9 C10 H10 119.8 . . ?
C4 C11 H11 119.4 . . ?
C12 C11 C4 121.21(13) . . ?
C12 C11 H11 119.4 . . ?
C1 C12 H12 119.7 . . ?
C11 C12 C1 120.59(14) . . ?
C11 C12 H12 119.7 . . ?
C14 C13 N1 120.43(8) 2_656 . ?
C14 C13 N1 120.43(8) . . ?
C14 C13 C14 119.15(16) . 2_656 ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.17(12) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.55(13) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C15 119.34(17) 2_656 . ?
C15 C16 H16 120.3 2_656 . ?
C15 C16 H16 120.3 . . ?
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 C6 1.4522(16) . ?
O1 C7 1.3338(16) . ?
O2 C7 1.2056(15) . ?
N1 C5 1.4252(13) 2_656 ?
N1 C5 1.4252(13) . ?
N1 C13 1.419(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.356(2) . ?
C1 C12 1.408(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.4196(18) . ?
C3 C4 1.4251(17) . ?
C3 C10 1.4085(19) . ?
C4 C5 1.4404(16) . ?
C4 C11 1.4209(18) . ?
C5 C8 1.3797(17) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.4959(17) . ?
C8 C9 1.4153(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3550(19) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.3669(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.3910(15) . ?
C13 C14 1.3910(15) 2_656 ?
C14 H14 0.9500 . ?
C14 C15 1.3842(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.3830(17) . ?
C16 C15 1.3830(17) 2_656 ?
C16 H16 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 C7 C8 C5 57.44(15) . . . . ?
O1 C7 C8 C9 -122.22(12) . . . . ?
O2 C7 C8 C5 -128.29(14) . . . . ?
O2 C7 C8 C9 52.05(16) . . . . ?
N1 C5 C8 C7 2.19(18) . . . . ?
N1 C5 C8 C9 -178.17(11) . . . . ?
N1 C13 C14 C15 -178.85(10) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
C1 C2 C3 C10 -176.29(13) . . . . ?
C2 C1 C12 C11 -1.7(2) . . . . ?
C2 C3 C4 C5 179.02(12) . . . . ?
C2 C3 C4 C11 -2.63(18) . . . . ?
C2 C3 C10 C9 176.66(13) . . . . ?
C3 C4 C5 N1 -177.96(10) . . . . ?
C3 C4 C5 C8 4.09(17) . . . . ?
C3 C4 C11 C12 2.30(19) . . . . ?
C4 C3 C10 C9 -0.5(2) . . . . ?
C4 C5 C8 C7 -179.88(11) . . . . ?
C4 C5 C8 C9 -0.24(18) . . . . ?
C4 C11 C12 C1 -0.2(2) . . . . ?
C5 N1 C5 C4 -130.64(12) 2_656 . . . ?
C5 N1 C5 C8 47.27(9) 2_656 . . . ?
C5 N1 C13 C14 -149.85(9) 2_656 . . . ?
C5 N1 C13 C14 30.15(9) . . . . ?
C5 N1 C13 C14 30.15(9) 2_656 . . 2_656 ?
C5 N1 C13 C14 -149.85(9) . . . 2_656 ?
C5 C4 C11 C12 -179.45(12) . . . . ?
C5 C8 C9 C10 -4.17(19) . . . . ?
C6 O1 C7 O2 0.01(17) . . . . ?
C6 O1 C7 C8 174.23(10) . . . . ?
C7 C8 C9 C10 175.51(12) . . . . ?
C8 C9 C10 C3 4.5(2) . . . . ?
C10 C3 C4 C5 -3.78(18) . . . . ?
C10 C3 C4 C11 174.57(12) . . . . ?
C11 C4 C5 N1 3.80(18) . . . . ?
C11 C4 C5 C8 -174.15(12) . . . . ?
C12 C1 C2 C3 1.3(2) . . . . ?
C13 N1 C5 C4 49.35(12) . . . . ?
C13 N1 C5 C8 -132.73(9) . . . . ?
C13 C14 C15 C16 -2.32(19) . . . . ?
C14 C13 C14 C15 1.15(10) 2_656 . . . ?
C14 C15 C16 C15 1.16(10) . . . 2_656 ?
