#------------------------------------------------------------------------------
#$Date: 2025-07-06 14:49:17 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 300407 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/46/7134616.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7134616
loop_
_publ_author_name
'Xu, Wei-Jian'
'Alikin, Denis'
'Fang, Zi-Luo'
'Romanyuk, Konstantin'
'Verissimo, Luis'
'Zelenovskii, Pavel'
'Zhang, Wei-Xiong'
'Kholkin, Andrei'
'Rocha, João'
_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           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 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                 102.173(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.8338(4)
_cell_length_b                   6.4470(4)
_cell_length_c                   10.1896(6)
_cell_measurement_reflns_used    3489
_cell_measurement_temperature    393
_cell_measurement_theta_max      27.1180
_cell_measurement_theta_min      2.0360
_cell_volume                     503.05(5)
_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      393
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7881
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.900
_diffrn_reflns_theta_min         2.045
_exptl_absorpt_coefficient_mu    4.034
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70007
_exptl_absorpt_correction_type   multi-scan
_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    1.533
_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         0.388
_refine_diff_density_min         -0.942
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     65
_refine_ls_number_reflns         1674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0439
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0546P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1049
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1216
_reflns_number_total             1674
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc01790d2.cif
_cod_data_source_block           2-ADAB_393K
_cod_depositor_comments
'Adding full bibliography for 7134614--7134616.cif.'
_cod_database_code               7134616
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.485
_shelx_estimated_absorpt_t_min   0.358
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H1C(0.5) H5A(0.5) H5B(0.5)
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C3(H3A,H3B)
3.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.66851(5) 0.2500 0.16251(3) 0.04611(17) Uani 1 2 d S T P . .
N1 N 0.4974(4) 0.7500 0.1666(3) 0.0421(7) Uani 1 2 d S T P . .
H1A H 0.5849 0.6591 0.1807 0.050 Uiso 0.5 1 calc GR . . A -1
H1B H 0.5388 0.8761 0.1561 0.050 Uiso 0.5 1 calc GR . . A -1
H1C H 0.4199 0.7148 0.0929 0.050 Uiso 0.5 1 calc GR . . A -1
C1 C 0.4108(4) 0.7500 0.2849(3) 0.0363(8) Uani 1 2 d S T P . .
H1 H 0.5030 0.7500 0.3665 0.044 Uiso 1 2 calc RS T P . .
C5 C -0.0289(4) 0.7500 0.3131(3) 0.0474(9) Uani 1 2 d S T P . .
H5A H -0.0998 0.6281 0.3182 0.057 Uiso 0.5 1 calc R . . . .
H5B H -0.0998 0.8719 0.3182 0.057 Uiso 0.5 1 calc R . . . .
C2 C 0.3007(3) 0.5574(4) 0.2878(3) 0.0456(6) Uani 1 1 d . . . . .
H2 H 0.3708 0.4331 0.2824 0.055 Uiso 1 1 calc R . . . .
C4 C 0.1283(5) 0.7500 0.4294(4) 0.0453(9) Uani 1 2 d S T P . .
H4 H 0.0893 0.7500 0.5147 0.054 Uiso 1 2 calc RS T P . .
C6 C 0.0316(5) 0.7500 0.1816(4) 0.0522(11) Uani 1 2 d S T P . .
H6 H -0.0702 0.7500 0.1068 0.063 Uiso 1 2 calc RS T P . .
C7 C 0.1417(4) 0.9407(6) 0.1725(3) 0.0597(9) Uani 1 1 d . . . . .
H7A H 0.0726 1.0646 0.1761 0.072 Uiso 1 1 calc R . . . .
H7B H 0.1792 0.9403 0.0876 0.072 Uiso 1 1 calc R . . . .
C3 C 0.2385(4) 0.5586(5) 0.4207(3) 0.0632(9) Uani 1 1 d . . . . .
H3A H 0.1700 0.4350 0.4269 0.076 Uiso 1 1 calc R . . . .
H3B H 0.3387 0.5577 0.4952 0.076 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 111.78(19) . 4_575 ?
N1 C1 C2 111.78(19) . . ?
C2 C1 C2 110.0(3) 4_575 . ?
C6 C5 C4 109.7(3) . . ?
C1 C2 C7 110.8(2) . 4_575 ?
C1 C2 C3 107.5(3) . . ?
C7 C2 C3 108.8(2) 4_575 . ?
C3 C4 C5 109.4(2) . . ?
C3 C4 C5 109.4(2) 4_575 . ?
C3 C4 C3 108.7(3) . 4_575 ?
C5 C6 C7 110.1(2) . . ?
C5 C6 C7 110.1(2) . 4_575 ?
C7 C6 C7 108.4(3) . 4_575 ?
C6 C7 C2 110.0(2) . 4_575 ?
C4 C3 C2 110.2(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.503(4) . ?
C1 C2 1.516(3) 4_575 ?
C1 C2 1.516(3) . ?
C5 C4 1.519(5) . ?
C5 C6 1.512(5) . ?
C2 C7 1.522(4) 4_575 ?
C2 C3 1.533(4) . ?
C4 C3 1.519(4) . ?
C4 C3 1.519(4) 4_575 ?
C6 C7 1.516(4) . ?
C6 C7 1.516(4) 4_575 ?
C7 C2 1.522(4) 4_575 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Br1 0.89 2.73 3.4946(12) 144.3 .
N1 H1B Br1 0.89 2.61 3.4946(12) 171.9 1_565
N1 H1C Br1 0.89 2.56 3.331(3) 145.7 2_655
