Pyrenyl substituted 1,8-naphthalimide as a new material for weak efficiency-roll-off red OLEDs: a theoretical and experimental study
Bezvikonnyi, Oleksandr; Gudeika, Dalius; Volyniuk, Dmytro; Grazulevicius, Juozas V.; Bagdziunas, Gintautas; New Journal of Chemistry 42 (2018) 12492–; doi:10.1039/C8NJ01866A

data_7057539
_publ_section_title
;
 Pyrenyl substituted 1,8-naphthalimide as a new material for weak
 efficiency-roll-off red OLEDs: a theoretical and experimental study
;
_journal_issue                   15
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12492
_journal_paper_doi               10.1039/C8NJ01866A
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         '2(C36 H31 N O2), C4 H8 O'
_chemical_formula_sum            'C76 H70 N2 O5'
_chemical_formula_weight         1091.34
_chemical_melting_point          413.5(5)
_chemical_name_common            ImPy
_chemical_name_systematic
'4-(1-pyrenyl)-N-(2-ethylhexyl)-1,8-naphthalimide '
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-06-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2018-03-17 deposited with the CCDC.
2018-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                78.37(4)
_cell_angle_beta                 79.43(5)
_cell_angle_gamma                89.40(6)
_cell_formula_units_Z            1
_cell_length_a                   9.290(13)
_cell_length_b                   12.67(2)
_cell_length_c                   13.427(18)
_cell_measurement_reflns_used    3247
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.10
_cell_volume                     1521(4)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15'
_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    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean 6.827
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0935
_diffrn_reflns_av_unetI/netI     0.0837
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8712
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.576
_diffrn_reflns_theta_min         3.116
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             580
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: THF'
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         6703
_refine_ls_number_restraints     727
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.1676
_refine_ls_R_factor_gt           0.1048
_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^)+(0.1056P)^2^+0.5684P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2721
_refine_ls_wR_factor_ref         0.3183
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3494
_reflns_number_total             6703
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj01866a1.cif
_cod_data_source_block           dg21
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '413-414' was changed to '413.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7057539.cif.
;
_cod_database_code               7057539
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.961
_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
 C38-C34 = C3AA-C38A = C38A-C30A = C38-C30 = C30A-C12A = C30-C12 = C40A-C12A =
 C40-C12 = C40-C37 = C40A-C37A
 1.54 with sigma of 0.02
 C5AA-O4AA = O4AA-C3 = C6AA-C3 = C6AA-C2 = C5AA-C2
 1.54 with sigma of 0.02
 C40A-C37A = C40-C37 = C37-C2AA
 1.54 with sigma of 0.02
 C37A-C2AA
 1.54 with sigma of 0.02
 C4AA-C37 = C37A-C2AA
 1.54 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C2 \\sim C6AA \\sim O4AA \\sim C3 \\sim C5AA: within 1.7A with sigma of 0.04
and sigma for terminal atoms of 0.08
C12 \\sim H12A \\sim H12B \\sim C30 \\sim H30 \\sim C34 \\sim H34A \\sim H34B
\\sim H34C \\sim C35 \\sim C37 \\sim C38 \\sim H38A \\sim H38B \\sim C40 \\sim
H40A \\sim H40B \\sim C38A \\sim H38C \\sim H38D \\sim C30A \\sim H30A \\sim
C12A \\sim H12C \\sim H12D \\sim C40A \\sim H40C \\sim H40D \\sim C37A \\sim
C3AA \\sim H3AA \\sim H3AB \\sim H3AC \\sim C2AA: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08
C12 \\sim H12A \\sim H12B \\sim C30 \\sim H30 \\sim C34 \\sim H34A \\sim H34B
\\sim H34C \\sim C35 \\sim H35A \\sim H35B \\sim H35C \\sim H35D \\sim C37
\\sim H37A \\sim H37B \\sim C38 \\sim H38A \\sim H38B \\sim C40 \\sim H40A
\\sim H40B \\sim C38A \\sim H38C \\sim H38D \\sim C30A \\sim H30A \\sim C12A
\\sim H12C \\sim H12D \\sim C40A \\sim H40C \\sim H40D \\sim C37A \\sim H37C
\\sim H37D \\sim C3AA \\sim H3AA \\sim H3AB \\sim H3AC \\sim C2AA \\sim H2AA
\\sim H2AB \\sim H2AC \\sim C4AA \\sim H4AA \\sim H4AB \\sim H4AC: within 1.7A
with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(C34) = Uanis(C3AA)
Uanis(C2AA) = Uanis(C4AA)
4. Others
 Fixed Sof: C12(0.5) H12A(0.5) H12B(0.5) C30(0.5) H30(0.5) C34(0.5) H34A(0.5)
 H34B(0.5) H34C(0.5) H35A(0.5) H35B(0.5) H35C(0.5) H35D(0.5) C37(0.5) H37A(0.5)
 H37B(0.5) C38(0.5) H38A(0.5) H38B(0.5) C40(0.5) H40A(0.5) H40B(0.5) C2(0.5)
 H2A(0.5) H2B(0.5) C6AA(0.5) H6AA(0.5) H6AB(0.5) C38A(0.5) H38C(0.5) H38D(0.5)
 C30A(0.5) H30A(0.5) C12A(0.5) H12C(0.5) H12D(0.5) C40A(0.5) H40C(0.5)
 H40D(0.5) C37A(0.5) H37C(0.5) H37D(0.5) C3AA(0.5) H3AA(0.5) H3AB(0.5)
 H3AC(0.5) O4AA(0.5) C3(0.5) H3A(0.5) H3B(0.5) C2AA(0.5) H2AA(0.5) H2AB(0.5)
 H2AC(0.5) C5AA(0.5) H5AA(0.5) H5AB(0.5) C4AA(0.5) H4AA(0.5) H4AB(0.5) H4AC(0.5)
5.a Ternary CH refined with riding coordinates:
 C30(H30), C30A(H30A)
5.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C35(H35A,H35B), C35(H35C,H35D), C37(H37A,H37B), C38(H38A,
 H38B), C40(H40A,H40B), C2(H2A,H2B), C6AA(H6AA,H6AB), C38A(H38C,H38D),
 C12A(H12C,H12D), C40A(H40C,H40D), C37A(H37C,H37D), C3(H3A,H3B), C5AA(H5AA,H5AB)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C11(H11), C17(H17), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24),
 C25(H25), C26(H26), C29(H29), C31(H31), C32(H32), C33(H33)
5.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C3AA(H3AA,H3AB,H3AC), C2AA(H2AA,H2AB,H2AC), C4AA(H4AA,
 H4AB,H4AC)
;
_shelx_res_checksum              4291
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'