#------------------------------------------------------------------------------
#$Date: 2025-07-06 14:49:17 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 300407 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/46/7134614.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_7134614
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           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-11
_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                 103.823(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.3591(5)
_cell_length_b                   6.3615(2)
_cell_length_c                   14.7799(6)
_cell_measurement_reflns_used    5416
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.6440
_cell_measurement_theta_min      2.0300
_cell_volume                     1037.08(7)
_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
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_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  0.0417
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17922
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.218
_diffrn_reflns_theta_min         2.584
_exptl_absorpt_coefficient_mu    3.913
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87399
_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    1.487
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         2990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0579
_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/[σ²(Fo²)+(0.0226P)²+1.5085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0936
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1967
_reflns_number_total             2990
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5cc01790d2.cif
_cod_data_source_block           1-ADAB_298K
_cod_depositor_comments
'Adding full bibliography for 7134614--7134616.cif.'
_cod_database_code               7134614
_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   0.494
_shelx_estimated_absorpt_t_min   0.377
_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.a Ternary CH refined with riding coordinates:
 C9(H9), C7(H7), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B), C4(H4A,H4B), C8(H8A,H8B), C6(H6A,H6B), C10(H10A,H10B)
2.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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.33254(3) 0.75279(6) 0.51811(2) 0.03776(11) Uani 1 1 d . . . . .
N1 N 0.4385(2) 0.2497(5) 0.58396(17) 0.0355(6) Uani 1 1 d . . . . .
H1A H 0.3968 0.3629 0.5594 0.043 Uiso 1 1 calc GR . . . .
H1B H 0.3918 0.1362 0.5702 0.043 Uiso 1 1 calc GR . . . .
H1C H 0.5034 0.2356 0.5607 0.043 Uiso 1 1 calc GR . . . .
C1 C 0.4781(3) 0.2742(5) 0.6884(2) 0.0248(6) Uani 1 1 d . . . . .
C9 C 0.6055(3) 0.4848(5) 0.8161(2) 0.0373(8) Uani 1 1 d . . . . .
H9 H 0.6623 0.6028 0.8312 0.045 Uiso 1 1 calc R . . . .
C7 C 0.4054(4) 0.3452(6) 0.8309(3) 0.0403(9) Uani 1 1 d . . . . .
H7 H 0.3342 0.3745 0.8553 0.048 Uiso 1 1 calc R . . . .
C3 C 0.5673(3) 0.4559(5) 0.7104(2) 0.0285(7) Uani 1 1 d . . . . .
H3A H 0.5297 0.5836 0.6812 0.034 Uiso 1 1 calc R . . . .
H3B H 0.6379 0.4262 0.6863 0.034 Uiso 1 1 calc R . . . .
C2 C 0.3665(3) 0.3175(5) 0.7251(2) 0.0333(8) Uani 1 1 d . . . . .
H2A H 0.3100 0.2012 0.7097 0.040 Uiso 1 1 calc R . . . .
H2B H 0.3264 0.4439 0.6965 0.040 Uiso 1 1 calc R . . . .
C4 C 0.5383(3) 0.0716(5) 0.7312(2) 0.0323(8) Uani 1 1 d . . . . .
H4A H 0.6083 0.0409 0.7067 0.039 Uiso 1 1 calc R . . . .
H4B H 0.4818 -0.0447 0.7159 0.039 Uiso 1 1 calc R . . . .
C8 C 0.4943(4) 0.5287(5) 0.8533(2) 0.0430(9) Uani 1 1 d . . . . .
H8A H 0.4552 0.6565 0.8254 0.052 Uiso 1 1 calc R . . . .
H8B H 0.5186 0.5491 0.9203 0.052 Uiso 1 1 calc R . . . .
C5 C 0.5775(3) 0.0992(5) 0.8372(2) 0.0392(9) Uani 1 1 d . . . . .
H5 H 0.6170 -0.0299 0.8655 0.047 Uiso 1 1 calc R . . . .
C6 C 0.4670(4) 0.1434(6) 0.8751(3) 0.0467(10) Uani 1 1 d . . . . .
H6A H 0.4912 0.1592 0.9422 0.056 Uiso 1 1 calc R . . . .
H6B H 0.4107 0.0267 0.8608 0.056 Uiso 1 1 calc R . . . .
C10 C 0.6668(4) 0.2831(5) 0.8607(3) 0.0474(10) Uani 1 1 d . . . . .
H10A H 0.6924 0.3005 0.9277 0.057 Uiso 1 1 calc R . . . .
H10B H 0.7381 0.2542 0.8373 0.057 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 C3 108.5(3) . . ?
N1 C1 C2 108.3(3) . . ?
N1 C1 C4 109.4(3) . . ?
C3 C1 C4 110.1(2) . . ?
C2 C1 C3 110.9(3) . . ?
C2 C1 C4 109.6(3) . . ?
C3 C9 C10 109.1(3) . . ?
C8 C9 C3 109.6(3) . . ?
C8 C9 C10 109.3(3) . . ?
C2 C7 C6 109.3(3) . . ?
C8 C7 C2 109.0(3) . . ?
C8 C7 C6 109.7(3) . . ?
C1 C3 C9 108.8(3) . . ?
C1 C2 C7 108.9(3) . . ?
C1 C4 C5 108.6(3) . . ?
C9 C8 C7 110.1(3) . . ?
C4 C5 C10 109.5(3) . . ?
C6 C5 C4 109.5(3) . . ?
C6 C5 C10 109.6(3) . . ?
C5 C6 C7 109.4(3) . . ?
C9 C10 C5 109.5(3) . . ?
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 1.509(4) . ?
C1 C3 1.520(4) . ?
C1 C2 1.518(4) . ?
C1 C4 1.524(4) . ?
C9 C3 1.529(5) . ?
C9 C8 1.519(5) . ?
C9 C10 1.532(5) . ?
C7 C2 1.530(5) . ?
C7 C8 1.528(5) . ?
C7 C6 1.531(5) . ?
C4 C5 1.533(5) . ?
C5 C6 1.518(5) . ?
C5 C10 1.533(5) . ?
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 2.62 3.475(3) 162.5 .
N1 H1B Br1 0.89 2.60 3.439(3) 158.1 1_545
N1 H1C Br1 0.89 2.42 3.304(3) 170.6 3_666
