#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:03:17 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228996 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/97/7229744.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_7229744
loop_
_publ_author_name
'Lu, Si-Qi'
'Chen, Xiao-Gang'
'Gao, Ji-Xing'
'Lu, Yang'
'Hua, Xiu-Ni'
'Liao, Wei-Qiang'
_publ_section_title
;
 High-temperature sequential structural transitions with distinct
 switchable dielectric behaviors in two organic ionic plastic crystals:
 [C4H11NBr] [ClO4] and [C4H11NBr] [BF4]
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              454
_journal_paper_doi               10.1039/C7CE01731F
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C4 H11 Br N, B F4'
_chemical_formula_sum            'C4 H11 B Br F4 N'
_chemical_formula_weight         239.85
_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'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-11-17 deposited with the CCDC.
2017-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.67(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0331(12)
_cell_length_b                   7.8583(16)
_cell_length_c                   9.5127(19)
_cell_measurement_reflns_used    1073
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.483
_cell_measurement_theta_min      1.6988
_cell_volume                     438.22(16)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku, SCXmini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4265
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         3.403
_exptl_absorpt_coefficient_mu    4.694
_exptl_absorpt_correction_T_max  0.391
_exptl_absorpt_correction_T_min  0.225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.818
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Sheet
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     62
_refine_ls_number_reflns         1070
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0450
_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)+(0.0273P)²+0.4959P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.000
_reflns_number_gt                897
_reflns_number_total             1073
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce01731f2.cif
_cod_data_source_block           P21M_CCDC1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7229742--7229745.cif.
;
_cod_database_code               7229744
_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_min   0.228
_shelx_estimated_absorpt_t_max   0.399
_shelx_res_file
;

    P21M.res created by SHELXL-2014/7


TITL P21M in P2(1)/m             New: P21/m
CELL  0.71073    6.0331    7.8583    9.5127    90.000   103.670    90.000
ZERR  2           0.0012    0.0016    0.0019     0.000     0.030     0.000
LATT 1
SYMM             - X ,    0.50000 + Y ,            - Z
SFAC C  H  B Br F N
UNIT 8 22 2 2 8 2
L.S. 50
ACTA
BOND $H
FMAP 2
PLAN 3
CONF
WGHT    0.027300    0.495900
FVAR       0.80857
BR1   4    0.578707    0.250000   -0.005585    10.50000    0.09511    0.05908 =
         0.04639    0.00000    0.03273    0.00000
F1    5    1.076587    0.250000    0.635791    10.50000    0.09166    0.11134 =
         0.08097    0.00000    0.05182    0.00000
F2    5    0.712117    0.250000    0.658755    10.50000    0.05521    0.08792 =
         0.06550    0.00000   -0.00228    0.00000
F3    5    0.979941    0.392615    0.819623    11.00000    0.08515    0.05294 =
         0.07929   -0.01696    0.01453   -0.00933
B1    3    0.940776    0.250000    0.732827    10.50000    0.04401    0.04079 =
         0.04243    0.00000    0.01031    0.00000
C1    1    0.360930    0.250000    0.112515    10.50000    0.05255    0.05411 =
         0.03690    0.00000    0.00411    0.00000
AFIX  23
H1A   2    0.264427    0.349789    0.089945    10.50000   -1.20000
H1B   2    0.264427    0.150211    0.089945    10.50000   -1.20000
AFIX   0
C2    1    0.283696    0.250000    0.348632    10.50000    0.05273    0.05255 =
         0.05921    0.00000    0.02532    0.00000
AFIX   3
H2A   2    0.348136    0.250000    0.449892    10.50000   -1.20000
H2B   2    0.198296    0.147630    0.328182    11.00000   -1.20000
AFIX   0
C3    1    0.614858    0.093725    0.313319    11.00000    0.05619    0.03769 =
         0.04789    0.00545    0.01020    0.01102
AFIX 137
H3A   2    0.737917    0.092969    0.265183    11.00000   -1.50000
H3B   2    0.521498   -0.005248    0.285550    11.00000   -1.50000
H3C   2    0.675692    0.092944    0.416131    11.00000   -1.50000
AFIX   0
N1    6    0.474091    0.250000    0.271482    10.50000    0.04089    0.03040 =
         0.03396    0.00000    0.00908    0.00000
HKLF 4

REM  P21M in P2(1)/m             New: P21/m
REM R1 =  0.0450 for     897 Fo > 4sig(Fo)  and  0.0560 for all    1070 data
REM     62 parameters refined using      0 restraints

END

WGHT      0.0517      0.1533

REM Highest difference peak  0.362,  deepest hole -0.324,  1-sigma level  0.091
Q1    1   0.4347  0.2500  0.0499  10.50000  0.05    0.36
Q2    1   1.0102  0.1488  0.6130  11.00000  0.05    0.33
Q3    1   0.7299  0.2500  0.0860  10.50000  0.05    0.29
;
_shelx_res_checksum              35099
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
Br1 Br 0.57871(11) 0.2500 -0.00559(6) 0.0642(3) Uani 1 2 d S T P
F1 F 1.0766(7) 0.2500 0.6358(4) 0.0894(12) Uani 1 2 d S T P
F2 F 0.7121(6) 0.2500 0.6588(4) 0.0723(10) Uani 1 2 d S T P
F3 F 0.9799(4) 0.3926(3) 0.8196(3) 0.0733(7) Uani 1 1 d . . .
B1 B 0.9408(9) 0.2500 0.7328(6) 0.0424(12) Uani 1 2 d S T P
C1 C 0.3609(9) 0.2500 0.1125(5) 0.0489(11) Uani 1 2 d S T P
H1A H 0.2644 0.3498 0.0899 0.059 Uiso 0.5 1 calc R U P
H1B H 0.2644 0.1502 0.0899 0.059 Uiso 0.5 1 calc R U P
C2 C 0.2837(9) 0.2500 0.3486(6) 0.0528(13) Uani 1 2 d S T P
H2A H 0.3481 0.2500 0.4499 0.063 Uiso 1 2 d R U P
H2B H 0.1983 0.1476 0.3282 0.063 Uiso 1 1 d R U .
C3 C 0.6149(6) 0.0937(4) 0.3133(4) 0.0476(8) Uani 1 1 d . . .
H3A H 0.7379 0.0930 0.2652 0.071 Uiso 1 1 calc R U .
H3B H 0.5215 -0.0052 0.2856 0.071 Uiso 1 1 calc R U .
H3C H 0.6757 0.0929 0.4161 0.071 Uiso 1 1 calc R U .
N1 N 0.4741(6) 0.2500 0.2715(4) 0.0350(8) Uani 1 2 d S T P
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0951(5) 0.0591(4) 0.0464(3) 0.000 0.0327(3) 0.000
F1 0.092(3) 0.111(3) 0.081(3) 0.000 0.052(2) 0.000
F2 0.055(2) 0.088(3) 0.065(2) 0.000 -0.0023(16) 0.000
F3 0.0851(17) 0.0529(13) 0.0793(17) -0.0170(12) 0.0145(14) -0.0093(12)
B1 0.044(3) 0.041(3) 0.042(3) 0.000 0.010(2) 0.000
C1 0.053(3) 0.054(3) 0.037(2) 0.000 0.004(2) 0.000
C2 0.053(3) 0.053(3) 0.059(3) 0.000 0.025(3) 0.000
C3 0.056(2) 0.0377(17) 0.0479(19) 0.0055(14) 0.0102(16) 0.0110(15)
N1 0.041(2) 0.0304(17) 0.0340(18) 0.000 0.0091(15) 0.000
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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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
F1 B1 F3 111.0(3) . .
F1 B1 F3 111.0(3) . 4_565
F3 B1 F3 108.7(4) . 4_565
F1 B1 F2 109.7(5) . .
F3 B1 F2 108.2(3) . .
F3 B1 F2 108.2(3) 4_565 .
N1 C1 Br1 112.2(3) . .
N1 C1 H1A 109.2 . .
Br1 C1 H1A 109.2 . .
N1 C1 H1B 109.2 . .
Br1 C1 H1B 109.2 . .
H1A C1 H1B 107.9 . .
N1 C2 H2A 108.6 . .
N1 C2 H2B 109.9 . .
H2A C2 H2B 106.2 . .
N1 C3 H3A 109.5 . .
N1 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
N1 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
C3 N1 C3 110.7(4) . 4_565
C3 N1 C2 108.8(2) . .
C3 N1 C2 108.8(2) 4_565 .
C3 N1 C1 111.2(2) . .
C3 N1 C1 111.2(2) 4_565 .
C2 N1 C1 105.9(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.920(5) .
F1 B1 1.371(6) .
F2 B1 1.393(7) .
F3 B1 1.379(4) .
B1 F3 1.379(4) 4_565
C1 N1 1.505(6) .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C2 N1 1.502(6) .
C2 H2A 0.9497 .
C2 H2B 0.9503 .
C3 N1 1.493(4) .
C3 H3A 0.9600 .
C3 H3B 0.9600 .
C3 H3C 0.9600 .
N1 C3 1.493(4) 4_565
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
Br1 C1 N1 C3 -62.0(2) .
Br1 C1 N1 C3 62.0(2) 4_565
Br1 C1 N1 C2 180.000(1) .
