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_7251284
_publ_section_title
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 Structural and computational study of reversibly photo switchable
 (E)-4-((4-alkoxyphenyl)diazenyl)benzonitrile based liquid crystals
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_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D5CE00980D
_journal_year                    2025
_chemical_formula_moiety         'C19 H21 N3 O'
_chemical_formula_sum            'C19 H21 N3 O'
_chemical_formula_weight         307.39
_chemical_name_common            (E)-4-((4-hexyloxyphenyl)diazenyl)benzonitrile
_chemical_name_systematic        Azonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
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2025-06-06 deposited with the CCDC.	2025-11-24 downloaded from the CCDC.
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_cell_angle_alpha                90
_cell_angle_beta                 93.01(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8120(12)
_cell_length_b                   7.4680(15)
_cell_length_c                   37.455(8)
_cell_measurement_reflns_used    3981
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      2.1
_cell_volume                     1623.5(6)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0476
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            23970
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         27.811
_diffrn_reflns_theta_min         2.145
_diffrn_source                   Synchrotron
_exptl_absorpt_coefficient_mu    0.076
_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    1.258
_exptl_crystal_density_meas      1.26
_exptl_crystal_description       'plate shaped'
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.153(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         3981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0825P)^2^+0.3428P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1348
_refine_ls_wR_factor_ref         0.1362
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3803
_reflns_number_total             3981
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00980d3.cif
_cod_data_source_block           AZN-6
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'multi scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               7251284
_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.a Free rotating group:
 O1(N2,N3,N1,C7,C4,C13,C10,C12,C9,C6,C3,C1,C5,C8,C11,C2,C16,C18,C14,C15,C17,C19)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B), C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C13(H13), C10(H10), C12(H12), C9(H9), C6(H6), C3(H3)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              26617
_olex2_submission_special_instructions 'No special instructions were received'