#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:03:17 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228996 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/97/7229743.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_7229743
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         'Cl O4, C4 H11 Br N'
_chemical_formula_sum            'C4 H11 Br Cl N O4'
_chemical_formula_weight         252.50
_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   difmap
_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                 101.49(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.250(12)
_cell_length_b                   8.164(16)
_cell_length_c                   9.64(2)
_cell_measurement_reflns_used    1169
_cell_measurement_temperature    363(2)
_cell_measurement_theta_max      27.348
_cell_measurement_theta_min      1.6988
_cell_volume                     482.0(17)
_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      363(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.970
_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  0.0812
_diffrn_reflns_av_unetI/netI     0.0754
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3359
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.348
_diffrn_reflns_theta_min         3.299
_exptl_absorpt_coefficient_mu    4.515
_exptl_absorpt_correction_T_max  0.405
_exptl_absorpt_correction_T_min  0.239
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.740
_exptl_crystal_description       'Thick sheet'
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.200
_refine_diff_density_max         3.370
_refine_diff_density_min         -1.278
_refine_diff_density_rms         0.342
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         1133
_refine_ls_number_restraints     47
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.2346
_refine_ls_R_factor_gt           0.1910
_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)+(0.2000P)²+13.8000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4587
_refine_ls_wR_factor_ref         0.4877
_reflns_Friedel_coverage         0.000
_reflns_number_gt                619
_reflns_number_total             1169
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7ce01731f2.cif
_cod_data_source_block           P21M
_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               7229743
_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   0.279
_shelx_estimated_absorpt_t_max   0.465
_shelx_res_file
;

    P21M.res created by SHELXL-2014/7


TITL P21M in P2(1)/m
CELL 0.71073   6.2502   8.1641   9.6360  90.000 101.492  90.000
ZERR    2.00   0.0121   0.0165   0.0202   0.000   0.037   0.000
LATT 1
SYMM -X, 0.5+Y, -Z
SFAC C  H  N  O  Cl Br
UNIT 8 22 2 8 2 2
L.S. 40
ACTA
BOND
FMAP 2
PLAN 4
SIZE 0.38 0.28 0.20
EADP O3 O3'
DFIX 2.35 0.02 O1 O2 O1 O3 O2 O3
DFIX 1.44 0.01 CL1 O2 CL1 O1 CL1 O3 CL1 O3'
DELU 0.01 CL1 O1 O2 O3 O3'
SIMU 0.01 CL1 O1 O2 O3 O3'
SIZE 0.38 0.28 0.20
TEMP 90
WGHT    0.200000   13.800000
FVAR       0.76392
BR1   6    0.575087    0.250000   -0.003831    10.50000    0.16345    0.10876 =
         0.07751    0.00000    0.06370    0.00000
CL1   5    0.949794    0.250000    0.726678    10.50000    0.06443    0.05210 =
         0.06399    0.00000    0.00359    0.00000
O1    4    1.100011    0.250000    0.634866    10.50000    0.11323    0.11512 =
         0.10526    0.00000    0.03825    0.00000
O2    4    0.724018    0.250000    0.665638    10.50000    0.07896    0.10714 =
         0.08860    0.00000   -0.01110    0.00000
O3    4    1.001744    0.120473    0.830433    10.50000    0.09565    0.05654 =
         0.09287    0.00535   -0.01060   -0.01129
O3'   4    0.944259    0.093710    0.796222    10.50000    0.09565    0.05654 =
         0.09287    0.00535   -0.01060   -0.01129
C1    1    0.356046    0.250000    0.119788    10.50000    0.11327    0.06973 =
         0.05034    0.00000    0.01272    0.00000
AFIX   3
H1A   2    0.264786    0.155050    0.098528    10.50000   -1.20000
H1B   2    0.264786    0.344950    0.098528    10.50000   -1.20000
AFIX   0
C2    1    0.273592    0.250000    0.359206    10.50000    0.11736    0.05360 =
         0.07129    0.00000    0.02805    0.00000
AFIX   3
H2A   2    0.183822    0.345960    0.339895    10.50000   -1.50000
H2B   2    0.183982    0.153940    0.340006    10.50000   -1.50000
H2C   2    0.346232    0.250000    0.456866    10.50000   -1.50000
AFIX   0
C3    1    0.591733    0.093060    0.301976    11.00000    0.06204    0.05151 =
         0.08968    0.00159    0.01023    0.02670
AFIX   3
H3A   2    0.699422    0.091340    0.243516    11.00000   -1.50000
H3B   2    0.663203    0.093730    0.399876    11.00000   -1.50000
H3C   2    0.500951   -0.002420    0.283016    11.00000   -1.50000
AFIX   0
N1    3    0.463634    0.250000    0.268036    10.50000    0.05611    0.03402 =
         0.04985    0.00000    0.02657    0.00000

HKLF 4

REM  P21M in P2(1)/m
REM R1 =  0.1910 for     619 Fo > 4sig(Fo)  and  0.2346 for all    1133 data
REM     64 parameters refined using     47 restraints

END

WGHT      0.2000      0.0000

REM Highest difference peak  3.370,  deepest hole -1.278,  1-sigma level  0.342
Q1    1   0.7425  0.1647  0.0757  11.00000  0.05    3.37
Q2    1   0.9400  0.2500  0.6894  10.50000  0.05    1.37
Q3    1   1.2441  0.2500  0.7174  10.50000  0.05    1.14
Q4    1   0.5159  0.2500  0.2437  10.50000  0.05    1.08
;
_shelx_res_checksum              3868
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 0.5751(8) 0.2500 -0.0038(4) 0.111(2) Uani 1 2 d S T P
Cl1 Cl 0.9498(10) 0.2500 0.7267(6) 0.0614(16) Uani 1 2 d DS TU P
O1 O 1.100(3) 0.2500 0.635(2) 0.109(6) Uani 1 2 d DS TU P
O2 O 0.7240(17) 0.2500 0.666(2) 0.095(5) Uani 1 2 d DS TU P
O3 O 1.002(4) 0.120(3) 0.830(2) 0.086(5) Uani 0.5 1 d D U P
O3' O 0.944(6) 0.094(2) 0.796(3) 0.086(5) Uani 0.5 1 d D U P
C1 C 0.356(6) 0.2500 0.120(3) 0.078(8) Uani 1 2 d S T P
H1A H 0.2648 0.1550 0.0985 0.094 Uiso 0.5 1 d R U P
H1B H 0.2648 0.3450 0.0985 0.094 Uiso 0.5 1 d R U P
C2 C 0.274(5) 0.2500 0.359(3) 0.079(8) Uani 1 2 d S T P
H2A H 0.1838 0.3460 0.3399 0.119 Uiso 0.5 1 d R U P
H2B H 0.1840 0.1539 0.3400 0.119 Uiso 0.5 1 d R U P
H2C H 0.3462 0.2500 0.4569 0.119 Uiso 1 2 d R U P
C3 C 0.592(3) 0.093(2) 0.302(2) 0.068(5) Uani 1 1 d . . .
H3A H 0.6994 0.0913 0.2435 0.103 Uiso 1 1 d R U .
H3B H 0.6632 0.0937 0.3999 0.103 Uiso 1 1 d R U .
H3C H 0.5010 -0.0024 0.2830 0.103 Uiso 1 1 d R U .
N1 N 0.464(3) 0.2500 0.2680(17) 0.044(4) 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 0.163(4) 0.109(3) 0.078(2) 0.000 0.064(2) 0.000
Cl1 0.064(3) 0.052(3) 0.064(3) 0.000 0.004(2) 0.000
O1 0.113(11) 0.115(13) 0.105(12) 0.000 0.038(9) 0.000
O2 0.079(8) 0.107(12) 0.089(11) 0.000 -0.011(8) 0.000
O3 0.096(10) 0.057(7) 0.093(9) 0.005(7) -0.011(7) -0.011(7)
O3' 0.096(10) 0.057(7) 0.093(9) 0.005(7) -0.011(7) -0.011(7)
C1 0.11(2) 0.070(16) 0.050(13) 0.000 0.013(13) 0.000
C2 0.12(3) 0.054(14) 0.071(16) 0.000 0.028(16) 0.000
C3 0.062(10) 0.052(9) 0.090(12) 0.002(8) 0.010(8) 0.027(8)
N1 0.056(10) 0.034(7) 0.050(8) 0.000 0.027(7) 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
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
O1 Cl1 O2 118.1(11) . .
O1 Cl1 O3' 111.8(18) . 4_565
O2 Cl1 O3' 94.5(14) . 4_565
O1 Cl1 O3' 111.8(18) . .
O2 Cl1 O3' 94.5(14) . .
O3' Cl1 O3' 124(3) 4_565 .
O1 Cl1 O3 110.3(12) . 4_565
O2 Cl1 O3 110.8(10) . 4_565
O3' Cl1 O3 19.4(16) 4_565 4_565
O3' Cl1 O3 110.3(15) . 4_565
O1 Cl1 O3 110.3(12) . .
O2 Cl1 O3 110.8(10) . .
O3' Cl1 O3 110.3(15) 4_565 .
O3' Cl1 O3 19.4(16) . .
O3 Cl1 O3 94(2) 4_565 .
N1 C1 Br1 111(2) . .
C1 N1 C3 109.5(11) . 4_565
C1 N1 C3 109.5(11) . .
C3 N1 C3 115.9(19) 4_565 .
C1 N1 C2 107(2) . .
C3 N1 C2 107.3(11) 4_565 .
C3 N1 C2 107.3(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.99(3) .
Cl1 O1 1.413(9) .
Cl1 O2 1.417(9) .
Cl1 O3' 1.445(10) 4_565
Cl1 O3' 1.445(10) .
Cl1 O3 1.447(9) 4_565
Cl1 O3 1.447(9) .
C1 N1 1.45(3) .
C2 N1 1.61(3) .
C3 N1 1.512(17) .
N1 C3 1.512(17) 4_565
