Structural and computational study of reversibly photo switchable (E)-4-((4-alkoxyphenyl)diazenyl)benzonitrile based liquid crystals
Thakur, Jyoti Swarup; Dash, Omkar; Bhale, Nagesh A.; Mondal, Pradip Kumar; Dikundwar, Amol Gopalrao; Polentarutti, Maurizio; Nayak, Susanta K.; CrystEngComm  (2025) –; doi:10.1039/D5CE00980D

data_7251282
_publ_section_title
;
 Structural and computational study of reversibly photo switchable
 (E)-4-((4-alkoxyphenyl)diazenyl)benzonitrile based liquid crystals
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D5CE00980D
_journal_year                    2025
_chemical_formula_moiety         'C16 H15 N3 O'
_chemical_formula_sum            'C16 H15 N3 O'
_chemical_formula_weight         265.31
_chemical_name_common            Azonitrile
_chemical_name_systematic        (E)-4-((4-propoxyphenyl)diazenyl)benzonitrile
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2025-06-06 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                73.39(3)
_cell_angle_beta                 87.85(3)
_cell_angle_gamma                88.91(3)
_cell_formula_units_Z            6
_cell_length_a                   5.9500(12)
_cell_length_b                   18.537(4)
_cell_length_c                   19.114(4)
_cell_measurement_reflns_used    11765
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      29.7
_cell_measurement_theta_min      1.1
_cell_volume                     2018.7(8)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Huber Kappa Goniometer, Pilatus 2M detector'
_diffrn_measurement_method       'Rotating crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            35341
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.749
_diffrn_reflns_theta_min         1.096
_diffrn_source                   Synchrotron
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2001)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      1.31
_exptl_crystal_description       'plate shaped'
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     580
_refine_ls_number_reflns         11765
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0632
_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^)+(0.1331P)^2^+0.2051P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1844
_refine_ls_wR_factor_ref         0.1918
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10388
_reflns_number_total             11765
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00980d3.cif
_cod_data_source_block           AZN-3
_cod_database_code               7251282
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.992
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C48)=Sof(H48A)=Sof(H48B)=Sof(C49)=Sof(H49A)=Sof(H49B)=Sof(H49C)=Sof(O4)=
 Sof(C50)=Sof(H50A)=Sof(H50B)=1-FVAR(1)
 Sof(O3)=Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(C47)=Sof(H47A)=Sof(H47B)=Sof(C51)=
 Sof(H51A)=Sof(H51B)=Sof(H51C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B), C50(H50A,H50B), C14(H14A,
 H14B), C15(H15A,H15B), C30(H30A,H30B), C31(H31A,H31B)
3.b Me refined with riding coordinates:
 C51(H51A,H51B,H51C), C49(H49A,H49B,H49C)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C18(H18),
 C19(H19), C21(H21), C22(H22), C24(H24), C25(H25), C27(H27), C28(H28), C34(H34),
  C35(H35), C37(H37), C38(H38), C40(H40), C41(H41), C43(H43), C44(H44)
3.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              87284
_olex2_submission_special_instructions 'No special instructions were received'