Synthesis and photophysical properties of pyridyl conjugated triazole appended naphthalenediimide derivatives.
Kumar, Girijesh; Guda, Ramu; Husain, Ahmad; Patra, Ranjan; Kirandeep, ?; Kasula, Mamatha; Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 18 (2019) 1333–1341; doi:10.1039/c9pp00003h

data_1550738
_publ_section_title
;
 Synthesis and photophysical properties of pyridyl conjugated triazole
 appended naphthalenediimide derivatives.
;
_journal_issue                   6
_journal_name_full
'Photochemical &amp; photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology'
_journal_page_first              1333
_journal_page_last               1341
_journal_paper_doi               10.1039/c9pp00003h
_journal_volume                  18
_journal_year                    2019
_chemical_formula_moiety         '2(C19 H10 N6 O2), C3 H6 N O'
_chemical_formula_sum            'C41 H26 N13 O5'
_chemical_formula_weight         780.75
_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             2017-03-14
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-03-14 deposited with the CCDC.    2019-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                62.734(2)
_cell_angle_beta                 68.276(2)
_cell_angle_gamma                76.955(2)
_cell_formula_units_Z            2
_cell_length_a                   12.5300(7)
_cell_length_b                   13.3747(7)
_cell_length_c                   13.8179(8)
_cell_measurement_reflns_used    5914
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      23.09
_cell_measurement_theta_min      2.37
_cell_volume                     1907.76(19)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      300.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            32913
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.370
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1085 before and 0.0546 after correction. The Ratio of minimum to maximum transmission is 0.8974. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       plate
_exptl_crystal_F_000             806
_exptl_crystal_preparation       ', Luminescent'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMF'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     534
_refine_ls_number_reflns         7718
_refine_ls_number_restraints     160
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1642
_refine_ls_R_factor_gt           0.0845
_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^)+(0.1603P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2369
_refine_ls_wR_factor_ref         0.2692
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3958
_reflns_number_total             7718
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9pp00003h2.cif
_cod_data_source_block           db41
_cod_depositor_comments          'Adding full bibliography for 1550738.cif.'
_cod_database_code               1550738
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.982
_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. Restrained distances
 N13-C40
 1.44 with sigma of 0.01
 N13-C39
 1.44 with sigma of 0.01
 N13-C41
 1.3 with sigma of 0.01
 O5-C41
 1.2 with sigma of 0.01
 N13-O5
 0.04 with sigma of 2.23
 C40-C39
 0.04 with sigma of 2.45
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C37(H37), C18(H18), C38(H38), C4(H4), C9(H9), C12(H12), C2(H2),
 C21(H21), C11(H11), C3(H3), C10(H10), C1(H1), C22(H22), C23(H23), C29(H29),
 C20(H20), C28(H28), C30(H30), C31(H31)
4.b Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C), C39(H39A,H39B,H39C)
;
_olex2_submission_special_instructions 'No special instructions were received'