Anthracene–naphthylacetonitrile fluorescent isomers and Cl/H substituent dependent molecular packing, solid-state fluorescence and mechanofluorochromism
Ravi, Sasikala; Priyadharshini, Prakash; Karthikeyan, Subramanian; Pannipara, Mehboobali; Al-Sehemi, Abdullah G.; Madhu, Vedichi; Moon, Dohyun; Anthony, Savarimuthu Philip; CrystEngComm 25 (2023) 6303–6309; doi:10.1039/D3CE00718A

data_7247516
_publ_section_title
;
 Anthracene--naphthylacetonitrile fluorescent isomers and Cl/H substituent
 dependent molecular packing, solid-state fluorescence and
 mechanofluorochromism
;
_journal_issue                   45
_journal_name_full               CrystEngComm
_journal_page_first              6303
_journal_page_last               6309
_journal_paper_doi               10.1039/D3CE00718A
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C27 H17 N'
_chemical_formula_sum            'C27 H17 N'
_chemical_formula_weight         355.42
_chemical_name_systematic
(Z)-3-(anthracen-9-yl)-2-(naphthalen-2-yl)acrylonitrile
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2023-07-18 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.10(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.818(4)
_cell_length_b                   5.3880(11)
_cell_length_c                   17.241(3)
_cell_measurement_reflns_used    59789
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      33.548
_cell_measurement_theta_min      0.361
_cell_volume                     1848.4(7)
_computing_cell_refinement       '<i>HKL3000sm</i>(Otwinowski & Minor, 1997)'
_computing_data_collection
'<i>PAL BL2D-SMDC Program</i>(Shin et.al, 2016)'
_computing_data_reduction        '<i>HKL3000sm</i>(Otwinowski & Minor, 1997)'
_computing_molecular_graphics    '<i>DIAMOND 4</i>(Putx&Brandenburg, 2014)'
_computing_publication_material  '<i>publCIF</i>(Westrip, 2010)'
_computing_structure_refinement  '<i>SHELXL-2018</i>(Sheldrick, 2018)'
_computing_structure_solution    '<i>SHELXT-2018</i>(Sheldrick, 2018)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.630
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16622
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        22.210
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.814
_diffrn_source                   'PLSII 2D bending magnet'
_exptl_absorpt_coefficient_mu    0.058
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
'<i>HKL3000sm Scalepack</i>(Otwinowski et.al,2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.074
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.009
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0475
_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^)+(0.0842P)^2^+0.1015P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1473
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3644
_reflns_number_total             4621
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00718a2.cif
_cod_data_source_block           SPA909
_cod_depositor_comments
'Adding full bibliography for 7247514--7247516.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7247516
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.996
_shelx_estimated_absorpt_t_max   0.999
_shelx_res_checksum              28110