Highly Efficient Deep-Blue Electroluminescence Based on a Solution-Processable A-π-D-π-A Oligo(p-phenyleneethynylene) Small Molecule.
Usta, Hakan; Alimli, Dilek; Ozdemir, Resul; Dabak, Salih; Zorlu, Yunus; Alkan, Fahri; Tekin, Emine; Can, Ayse; ACS applied materials & interfaces  (2019) –; doi:10.1021/acsami.9b12971

data_4515204
_publ_section_title
;
 Highly Efficient Deep-Blue Electroluminescence Based on a
 Solution-Processable A-\p-D-\p-A Oligo(p-phenyleneethynylene) Small
 Molecule.
;
_journal_name_full               'ACS applied materials &amp; interfaces'
_journal_paper_doi               10.1021/acsami.9b12971
_journal_year                    2019
_chemical_formula_moiety         'C40 H44 N2 O2'
_chemical_formula_sum            'C40 H44 N2 O2'
_chemical_formula_weight         584.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-10-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.649(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8605(8)
_cell_length_b                   11.7357(10)
_cell_length_c                   14.9221(12)
_cell_measurement_reflns_used    3503
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.48
_cell_measurement_theta_min      2.21
_cell_volume                     1724.9(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      172.99
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11829
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.068
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS)'
_exptl_crystal_colour            green
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_description       plate
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.381
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   0.98
_exptl_transmission_factor_min   0.97
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3012
_refine_ls_number_restraints     164
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1326
_refine_ls_R_factor_gt           0.0693
_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/[\s^2^(Fo^2^)+(0.0911P)^2^+0.6560P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1716
_refine_ls_wR_factor_ref         0.2066
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1644
_reflns_number_total             3012
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            am9b12971_si_002.cif
_cod_data_source_block           18gtu282
_cod_database_code               4515204
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.974
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C20-C19
 1.55 with sigma of 0.02
 C19-C18
 1.55 with sigma of 0.02
 C18-C17
 1.55 with sigma of 0.02
 C17-C16
 1.55 with sigma of 0.02
 C16-C15
 1.55 with sigma of 0.02
 C15-C14
 1.55 with sigma of 0.02
 C21-C22
 1.55 with sigma of 0.02
 C22-C23
 1.55 with sigma of 0.02
 C23-C24
 1.55 with sigma of 0.02
 C24-C25
 1.55 with sigma of 0.02
 C25-C26
 1.55 with sigma of 0.02
 C26-C27
 1.55 with sigma of 0.02
 C13-C16 \\sim C13-C25
 with sigma of 0.02
 C16-C15 \\sim C25-C26
 with sigma of 0.02
 C16-C17 \\sim C25-C24
 with sigma of 0.02
 C15-C14 \\sim C26-C27
 with sigma of 0.02
 C17-C18 \\sim C24-C23
 with sigma of 0.02
 C19-C18 \\sim C22-C23
 with sigma of 0.02
 C19-C20 \\sim C22-C21
 with sigma of 0.02
 C13-C15 \\sim C13-C26
 with sigma of 0.04
 C13-C17 \\sim C13-C24
 with sigma of 0.04
 C16-C18 \\sim C25-C23
 with sigma of 0.04
 C16-C14 \\sim C25-C27
 with sigma of 0.04
 C15-C17 \\sim C26-C24
 with sigma of 0.04
 C17-C19 \\sim C24-C22
 with sigma of 0.04
 C18-C20 \\sim C23-C21
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C19 \\sim C20: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.08
C18 \\sim C19: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.08
C17 \\sim C18: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.08
C16 \\sim C17: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.08
C15 \\sim C16: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.08
C14 \\sim C15: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.08
C26 \\sim C27: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.08
C25 \\sim C26: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.08
C24 \\sim C25: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.08
C23 \\sim C24: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.08
C22 \\sim C23: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.08
C21 \\sim C22: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.08
4. Rigid body (RIGU) restrains
 C14, C15, C16, C17, C18, C19, C20
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C21, C22, C23, C24, C25, C26, C27
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H13C)=Sof(H13D)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C22)=Sof(H22A)=
 Sof(H22B)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(C25)=
 Sof(H25)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=1-
 FVAR(1)
 Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=Sof(C15)=Sof(H15A)=
 Sof(H15B)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(C18)=Sof(H18A)=
 Sof(H18B)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=
 FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C16(H16), C25(H25)
6.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C13(H13C,H13D), C15(H15A,H15B), C17(H17A,H17B), C18(H18A,
 H18B), C19(H19A,H19B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B),
 C26(H26A,H26B)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C11(H11)
6.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C27(H27A,H27B,
 H27C)
;
_olex2_submission_special_instructions 'No special instructions were received'