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_7247515
_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         'C54 H33 Cl N2'
_chemical_formula_sum            'C54 H33 Cl N2'
_chemical_formula_weight         745.27
_chemical_name_systematic
(Z)-3-(anthracen-9-yl)-2-(naphthalen-2-yl)acrylonitrile
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/2
_audit_update_record
;
2023-07-18 deposited with the CCDC.	2023-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.899(3)
_cell_length_b                   5.5020(11)
_cell_length_c                   41.337(8)
_cell_measurement_reflns_used    78736
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      33.749
_cell_measurement_theta_min      0.401
_cell_volume                     3843.4(13)
_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 0.955
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            25422
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_min         1.941
_diffrn_source                   'PLSII 2D bending magnet'
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.925
_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    1.288
_exptl_crystal_description       plate
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.071
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.17(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     526
_refine_ls_number_reflns         7495
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0419
_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^)+(0.0700P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1166
_reflns_Friedel_coverage         0.963
_reflns_Friedel_fraction_full    0.946
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                6006
_reflns_number_total             7495
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00718a2.cif
_cod_data_source_block           SPA873
_cod_depositor_comments
'Adding full bibliography for 7247514--7247516.cif.'
_cod_database_code               7247515
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_min   0.991
_shelx_estimated_absorpt_t_max   0.998
_shelx_res_checksum              40238