Construction of highly efficient near-IR solid emitter based on naphthalene diimide with AIE-active tetraphenylethene periphery
Rananaware, Anushri; La, Duong Duc; Leslie Jackson, Sam; Bhosale, Sheshanath V.; RSC Adv.  (2016) –; doi:10.1039/C6RA00907G

data_7224151
_publ_section_title
;
 Construction of highly efficient near-IR solid emitter based on
 naphthalene diimide with AIE-active tetraphenylethene periphery
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA00907G
_journal_year                    2016
_chemical_formula_moiety         'C134 H110 N6 O4, 2(C2 H2 Cl3), 4(C H Cl3)'
_chemical_formula_sum            'C142 H118 Cl18 N6 O4'
_chemical_formula_weight         2610.52
_chemical_name_systematic        '4-(1, 2, 2-triphenylvinyl) aniline '
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-06-12
_audit_creation_method
;
Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.
;
_audit_update_record
;
2015-06-12 deposited with the CCDC.
2016-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                95.031(8)
_cell_angle_beta                 107.348(7)
_cell_angle_gamma                110.750(8)
_cell_formula_units_Z            1
_cell_length_a                   13.423(6)
_cell_length_b                   14.682(6)
_cell_length_c                   18.745(8)
_cell_measurement_temperature    200(2)
_cell_volume                     3219(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL XPREP'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'APEX II CCD detector'
_diffrn_measurement_method       CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_unetI/netI     0.1317
_diffrn_reflns_laue_measured_fraction_full 0.581
_diffrn_reflns_laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12928
_diffrn_reflns_point_group_measured_fraction_full 0.581
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.242
_diffrn_reflns_theta_min         1.703
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sheldrick, G. M., SADABS 1997'
_exptl_crystal_colour            'dark black'
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needles
_exptl_crystal_F_000             1350
_exptl_crystal_recrystallization_method 'Vapour Deposition'
_exptl_crystal_size_max          0.576
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     802
_refine_ls_number_reflns         6978
_refine_ls_number_restraints     113
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.1916
_refine_ls_R_factor_gt           0.0987
_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^)+(0.1840P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2503
_refine_ls_wR_factor_ref         0.2955
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3216
_reflns_number_total             6978
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra00907g2.cif
_cod_data_source_block           shelxl
_cod_database_code               7224151
_exptl_crystal_f_000'            1353.08
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C67-C66
 1.5 with sigma of 0.02
 C63-C62
 1.54 with sigma of 0.02
 C65-C64 \\sim C64-C63
 with sigma of 0.02
 C64-C63 \\sim C62-C61
 with sigma of 0.02
 Cl7-Cl8 \\sim Cl7-Cl12 \\sim Cl12-Cl8
 with sigma of 0.02
 C63-C64 \\sim C65-C66
 with sigma of 0.02
 C69-Cl7 \\sim C69-Cl8 \\sim C69-Cl12
 with sigma of 0.02
 Cl9-C70 \\sim C70-Cl10
 with sigma of 0.02
 Cl9-C70 \\sim C70-Cl11
 with sigma of 0.02
 Cl10-C70 \\sim C70-Cl11
 with sigma of 0.02
 C72-Cl6 \\sim C72-Cl4 \\sim C72-Cl5
 with sigma of 0.02
 C71-Cl5 \\sim C71-Cl6 \\sim C71-Cl4
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C60 \\sim C61: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
C62 \\sim C63: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
C62 \\sim C64 \\sim C61 \\sim C63: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
Cl11 \\sim Cl10 \\sim Cl9: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
Cl11 \\sim Cl10 \\sim Cl9 \\sim Cl7 \\sim Cl8 \\sim Cl12: within 1.7A with
sigma of 0.04 and sigma for terminal atoms of 0.08
C8 \\sim N3 \\sim C7: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
C34 \\sim N2 \\sim C6: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
N3 \\sim N2 \\sim N1: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
Cl3 \\sim Cl2 \\sim Cl1 \\sim Cl7 \\sim Cl8 \\sim Cl12: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08
C64 \\sim C65 \\sim C66 \\sim C63: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
C60 \\sim C62 \\sim C64 \\sim C65 \\sim C61 \\sim C66 \\sim C63: within 1.7A
with sigma of 0.04 and sigma for terminal atoms of 0.08
Cl7 \\sim Cl8 \\sim C69 \\sim Cl12: within 1.7A with sigma of 0.02 and sigma
for terminal atoms of 0.04
Cl11 \\sim Cl10 \\sim Cl9 \\sim C70: within 1.7A with sigma of 0.02 and sigma
for terminal atoms of 0.04
Cl5 \\sim Cl4 \\sim Cl6 \\sim C72 \\sim C71: within 1.7A with sigma of 0.04 and
sigma for terminal atoms of 0.08
C71 \\sim C72: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04
4. Others
 Fixed Sof: H60A(0) H60B(0) Cl11(0.5) Cl10(0.5) Cl9(0.5) C70(0.5) H70(0.5)
 Cl7(0.5) Cl8(0.5) C69(0.5) H69(0.5) Cl12(0.5)
5.a Ternary CH refined with riding coordinates:
 C68(H68), C72(H72), C71(H71), C70(H70), C69(H69)
5.b Secondary CH2 refined with riding coordinates:
 C60(H60A,H60B), C62(H62A,H62B), C64(H64A,H64B), C65(H65A,H65B), C61(H61A,
 H61B), C66(H66A,H66B), C63(H63A,H63B)
5.c Me refined with riding coordinates:
 C67(H67A,H67B,H67C)
5.d Aromatic/amide H refined with riding coordinates:
 C13(H13), C12(H12), C9(H9), C10(H10), C26(H26), C27(H27), C23(H23), C24(H24),
 C25(H25), C33(H33), C29(H29), C30(H30), C31(H31), C32(H32), C53(H53), C52(H52),
  C51(H51), C50(H50), C49(H49), C43(H43), C47(H47), C46(H46), C55(H55),
 C59(H59), C58(H58), C57(H57), C56(H56), C36(H36), C35(H35), C39(H39), C38(H38),
  N2(H2), N3(H3), C45(H45), C44(H44), C17(H17), C21(H21), C20(H20), C19(H19),
 C18(H18)
;
_shelx_res_checksum              92722