Unlocking ferroelectricity in a metal-free adamantane derivative via targeted symmetry reduction
Xu, Wei-Jian; Alikin, Denis; Fang, Zi-Luo; Romanyuk, Konstantin; Verissimo, Luis; Zelenovskii, Pavel; Zhang, Wei-Xiong; Kholkin, Andrei; Rocha, João; Chemical Communications 61 (2025) 9286–9289; doi:10.1039/D5CC01790D

data_7134615
_publ_section_title
;
 Unlocking ferroelectricity in a metal-free adamantane derivative via
 targeted symmetry reduction
;
_journal_issue                   51
_journal_name_full               'Chemical Communications'
_journal_page_first              9286
_journal_page_last               9289
_journal_paper_doi               10.1039/D5CC01790D
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'Br, C10 H18 N'
_chemical_formula_sum            'C10 H18 Br N'
_chemical_formula_weight         232.16
_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             2024-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2024-04-01 deposited with the CCDC.	2025-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.526(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.7656(3)
_cell_length_b                   6.4026(2)
_cell_length_c                   10.1581(4)
_cell_measurement_reflns_used    4019
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      29.7180
_cell_measurement_theta_min      2.0520
_cell_volume                     493.04(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7256
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.952
_diffrn_reflns_theta_min         2.054
_exptl_absorpt_coefficient_mu    4.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69292
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.18(2)
_refine_ls_extinction_coef       0.065(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0346
_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^)+(0.0344P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0712
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                2328
_reflns_number_total             2685
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01790d2.cif
_cod_data_source_block           2-ADAB_298K
_cod_depositor_comments
'Adding full bibliography for 7134614--7134616.cif.'
_cod_database_code               7134615
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.479
_shelx_estimated_absorpt_t_min   0.353
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.82(2)
 0.18(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All N(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C7(H7), C2(H2), C1(H1), C9(H9), C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C8(H8A,H8B), C3(H3A,H3B), C5(H5A,H5B), C4(H4A,H4B)
3.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_shelx_res_checksum              8235
_shelx_hkl_checksum              12809
_olex2_submission_special_instructions 'No special instructions were received'