Excitation wavelength-dependent multi-coloured and white-light emissive pyrene-based hydrazones: suppression of Kasha's rule
Pramanik, Susnata; Khatua, Snehadrinarayan; Gaikwad, Sudhakar; Lyngkhoi, Deikrisha Lyngdoh; Kumar, Naveen; Ahamed, Rafiq; Samanta, Jayanta; Chemical Communications  (2023) –; doi:10.1039/D3CC04584F

data_7132302
_publ_section_title
;
 Excitation wavelength-dependent multi-coloured and white-light emissive
 pyrene-based hydrazones: suppression of Kasha's rule
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04584F
_journal_year                    2023
_chemical_formula_moiety         '1.998(C11.009 H6.979 N0.997 O0.498)'
_chemical_formula_sum            'C22 H13.98 N2 O'
_chemical_formula_weight         322.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2023-09-12 deposited with the CCDC.	2023-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.011(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9310(11)
_cell_length_b                   4.4906(3)
_cell_length_c                   23.0319(16)
_cell_measurement_reflns_used    3716
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      25.42
_cell_measurement_theta_min      2.23
_cell_volume                     1544.27(19)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0951
_diffrn_reflns_av_unetI/netI     0.1072
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            19788
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.676
_diffrn_reflns_theta_min         2.234
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1285 before and 0.1007 after correction.
The Ratio of minimum to maximum transmission is 0.8062.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.137
_refine_ls_abs_structure_details
;
 Flack x determined using 997 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.4(10)
_refine_ls_extinction_coef       0.29(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.460
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     797
_refine_ls_number_reflns         5771
_refine_ls_number_restraints     2450
_refine_ls_restrained_S_all      1.250
_refine_ls_R_factor_all          0.1898
_refine_ls_R_factor_gt           0.1490
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3912
_refine_ls_wR_factor_ref         0.4230
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                3513
_reflns_number_total             5771
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04584f2.cif
_cod_data_source_block           1
_cod_database_code               7132302
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.983
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 C26B_2-C25B_2 = C43B_1-C7B_1
 1.4 with sigma of 0.02
 C31B_2-C32B_2 = C30B_2-C31B_2 = C30B_2-C29B_2 = C29B_2-C38B_2
 1.39 with sigma of 0.02
 C42B_1-C12B_1 = C30B_1-C12B_1 = C10B_1-C30B_1 = C10B_1-C6B_1
 1.39 with sigma of 0.02
 C27B_2-C26B_2 = C28B_2-C27B_2 = C28B_2-C29B_2 = C29B_2-C38B_2 = C38B_2-C25B_2
 = C26B_2-C25B_2 = C7B_1-C43B_1 = C7B_1-C17B_1 = C17B_1-C29B_1 = C29B_1-C12B_1 =
  C42B_1-C12B_1
 1.39 with sigma of 0.02
 C21B_1-C9B_1 = O2B_2-C23B_2
 1.4 with sigma of 0.02
 C22B_2-N1B_2 \\sim N1B_2-C18B_2
 with sigma of 0.02
 C32B_1-C25B_1 \\sim C25B_1-C36B_1
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.03 and sigma
for terminal atoms of 0.03 within 2A
Uanis(C22B_2) \\sim Ueq, Uanis(C32B_1) \\sim Ueq, Uanis(C21B_2) \\sim Ueq,
Uanis(C35B_1) \\sim Ueq, Uanis(C20B_2) \\sim Ueq, Uanis(C34B_1) \\sim Ueq,
Uanis(C19B_2) \\sim Ueq, Uanis(C33B_1) \\sim Ueq, Uanis(C18B_2) \\sim Ueq,
Uanis(C37B_1) \\sim Ueq, Uanis(C17B_2) \\sim Ueq, Uanis(C36B_1) \\sim Ueq,
Uanis(C26B_1) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O1B)=Sof(N1B)=Sof(H1B)=Sof(N2B)=Sof(C1B)=Sof(C2B)=Sof(C3B)=Sof(C4B)=
 Sof(H4B)=Sof(C5B)=Sof(H5B)=Sof(C6B)=Sof(H6B)=Sof(C7B)=Sof(C8B)=Sof(H8B)=
 Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(C12B)=Sof(H12B)=Sof(C13B)=Sof(H13B)=Sof(C14B)=
 Sof(C15B)=Sof(C16B)=Sof(C17B)=Sof(C18B)=Sof(H18B)=Sof(C19B)=Sof(H19B)=
 Sof(C20B)=Sof(H20B)=Sof(C21B)=Sof(H21B)=Sof(C22B)=Sof(H22B)=1-FVAR(1)
 Sof(C18B)=Sof(C23B)=Sof(C25B)=Sof(H)=Sof(C1B)=Sof(H1B)=Sof(C2B)=Sof(H2B)=
 Sof(C14B)=Sof(H14B)=Sof(O1B)=Sof(N2B)=Sof(C3B)=Sof(C13B)=Sof(C15B)=Sof(H15B)=
 Sof(N1B)=Sof(HA)=Sof(C16B)=Sof(H16B)=Sof(C4B)=Sof(C24B)=Sof(H24B)=Sof(C26B)=
 Sof(C37B)=Sof(C36B)=Sof(H36B)=Sof(C35B)=Sof(H35B)=Sof(C34B)=Sof(H34B)=
 Sof(C33B)=Sof(H33B)=Sof(C32B)=Sof(H32B)=Sof(C38B)=Sof(H38B)=Sof(N3B)=FVAR(1)
 Sof(O2B)=Sof(N3B)=Sof(N4B)=Sof(H4BA)=Sof(C23B)=Sof(C24B)=Sof(C25B)=Sof(C38B)=
 Sof(C37B)=Sof(C36B)=Sof(C35B)=Sof(H35B)=Sof(C34B)=Sof(H34B)=Sof(C33B)=
 Sof(H33B)=Sof(C32B)=Sof(C26B)=Sof(H26B)=Sof(C27B)=Sof(H27B)=Sof(C28B)=
 Sof(H28B)=Sof(C29B)=Sof(C30B)=Sof(H30B)=Sof(C31B)=Sof(H31B)=Sof(C44B)=
 Sof(H44B)=Sof(C43B)=Sof(H43B)=Sof(C42B)=Sof(H42B)=Sof(C41B)=Sof(H41B)=
 Sof(C40B)=Sof(H40B)=Sof(C39B)=1-FVAR(2)
 Sof(C21B)=Sof(C5B)=Sof(C11B)=Sof(HB)=Sof(C7B)=Sof(H7B)=Sof(C9B)=Sof(C44B)=
 Sof(C43B)=Sof(C42B)=Sof(C41B)=Sof(C40B)=Sof(C39B)=Sof(H39B)=Sof(C22B)=
 Sof(H22B)=Sof(C8B)=Sof(H8B)=Sof(C6B)=Sof(C10B)=Sof(H10B)=Sof(C12B)=Sof(C17B)=
 Sof(H17B)=Sof(C29B)=Sof(H29B)=Sof(C30B)=Sof(H30B)=Sof(C31B)=Sof(H31B)=
 Sof(C27B)=Sof(H27B)=Sof(C19B)=Sof(C28B)=Sof(H28B)=Sof(O2B)=Sof(HC)=Sof(C20B)=
 Sof(H20B)=FVAR(2)
 Sof(C11B)=Sof(H11B)=1-FVAR(3)
 Sof(N4B)=FVAR(3)
6.a Aromatic/amide H refined with riding coordinates:
 C11B(HB), C25B(H), C1B(H1B), C2B(H2B), C14B(H14B), C15B(H15B), N1B(HA),
 C16B(H16B), C7B(H7B), C39B(H39B), C22B(H22B), C8B(H8B), C10B(H10B), C17B(H17B),
  C24B(H24B), C29B(H29B), C30B(H30B), C31B(H31B), C27B(H27B), C28B(H28B),
 O2B(HC), C20B(H20B), C36B(H36B), C35B(H35B), C34B(H34B), C33B(H33B),
 C32B(H32B), C38B(H38B), N1B(H1B), N4B(H4BA), C4B(H4B), C5B(H5B), C6B(H6B),
 C8B(H8B), C9B(H9B), C11B(H11B), C12B(H12B), C13B(H13B), C18B(H18B), C19B(H19B),
  C20B(H20B), C21B(H21B), C22B(H22B), C35B(H35B), C34B(H34B), C33B(H33B),
 C26B(H26B), C27B(H27B), C28B(H28B), C30B(H30B), C31B(H31B), C44B(H44B),
 C43B(H43B), C42B(H42B), C41B(H41B), C40B(H40B)
6.b Fitted hexagon refined as free rotating group:
 C31B(C27B,C19B,C28B,O2B,C20B), C37B(C36B,C35B,C34B,C33B,C32B), C44B(C43B,C42B,
 C41B,C40B,C39B)
6.c Naphthalene refined as free rotating group:
 C2B(C14B,O1B,N2B,C3B,C13B,C15B,N1B,C16B,C4B), C9B(C44B,C43B,C42B,C41B,C40B,
 C39B,C22B,C8B,C6B), C23B(C24B,C25B,C38B,C37B,C36B,C35B,C34B,C33B,C32B)
;
_shelx_res_checksum              49339
_shelx_hkl_checksum              90422
_olex2_submission_special_instructions 'No special instructions were received'