#------------------------------------------------------------------------------
#$Date: 2021-05-14 06:21:55 +0200 (vie 14 de may de 2021) $
#$Revision: 265210 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/28/7242853.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_7242853
loop_
_publ_author_name
'Owczarek, Magdalena'
'Szklarz, Przemysław'
'Jakubas, Ryszard'
_publ_section_title
;
 Towards ferroelectricity-inducing chains of halogenoantimonates(iii) and
 halogenobismuthates(iii)
;
_journal_issue                   29
_journal_name_full               'RSC Advances'
_journal_page_first              17574
_journal_page_last               17586
_journal_paper_doi               10.1039/D0RA10151F
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'Bi Br5, 2(C4 H6 N3)'
_chemical_formula_sum            'C8 H12 Bi Br5 N6'
_chemical_formula_weight         800.77
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-08-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-26 deposited with the CCDC.	2021-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                115.801(5)
_cell_angle_beta                 96.295(3)
_cell_angle_gamma                98.857(3)
_cell_formula_units_Z            2
_cell_length_a                   7.8733(3)
_cell_length_b                   11.4038(5)
_cell_length_c                   11.6180(5)
_cell_measurement_reflns_used    5859
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.5440
_cell_measurement_theta_min      3.3250
_cell_volume                     909.46(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_detector_type            'Sapphire2, large Be window'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.567
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00  69.50   0.75   30.00    --   28.00 -79.00   0.00  186
  2  ω    -70.00  69.50   0.75   30.00    --   28.00 -79.00  90.00  186
  3  ω    -70.00  69.50   0.75   30.00    --   28.00 -79.00 180.00  186
  4  ω    -70.00  69.50   0.75   30.00    --   28.00 -79.00 270.00  186
  5  ω    -54.00  60.00   0.75   50.00    --   48.00 -79.00  45.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0342251000
_diffrn_orient_matrix_UB_12      -0.0588107000
_diffrn_orient_matrix_UB_13      -0.0598369000
_diffrn_orient_matrix_UB_21      -0.0087018000
_diffrn_orient_matrix_UB_22      0.0395608000
_diffrn_orient_matrix_UB_23      -0.0325141000
_diffrn_orient_matrix_UB_31      0.0860660000
_diffrn_orient_matrix_UB_32      -0.0021123000
_diffrn_orient_matrix_UB_33      -0.0122301000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.567
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9692
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.567
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.673
_diffrn_reflns_theta_min         2.972
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    20.675
_exptl_absorpt_correction_T_max  0.481
_exptl_absorpt_correction_T_min  0.035
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.924
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.038
_refine_diff_density_max         2.716
_refine_diff_density_min         -2.757
_refine_diff_density_rms         0.400
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         5132
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0546
_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)+(0.0756P)²+5.6399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1377
_refine_ls_wR_factor_ref         0.1499
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4358
_reflns_number_total             5132
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra10151f2.cif
_cod_data_source_block           2apyrimabs
_cod_original_cell_volume        909.46(7)
_cod_database_code               7242853
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C8 H12 Bi Br5 N6'
_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.
;
_reflns_odcompleteness_completeness 99.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1A(H1A), C5A(H5A), N1B(H1B), C6A(H6A), C4A(H4A), C6B(H6B), C4B(H4B), C5B(H5B)
2.b X=CH2 refined with riding coordinates:
 N2A(H2AA,H2AB), N2B(H2BA,H2BB)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.572
_oxdiff_exptl_absorpt_empirical_full_min 0.655
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
Bi Bi 0.53421(4) 0.17160(3) 0.69515(2) 0.01589(12) Uani 1 1 d . . . . .
Br5 Br 0.29628(12) 0.27251(9) 0.85852(8) 0.0201(2) Uani 1 1 d . . . . .
Br3 Br 0.76511(12) 0.05453(9) 0.51492(8) 0.0212(2) Uani 1 1 d . . . . .
Br4 Br 0.47705(13) 0.33987(9) 0.56548(8) 0.0219(2) Uani 1 1 d . . . . .
Br1 Br 0.82137(12) 0.36133(9) 0.86152(7) 0.0227(2) Uani 1 1 d . . . . .
Br2 Br 0.57962(13) 0.01698(10) 0.81647(8) 0.0235(2) Uani 1 1 d . . . . .
N1A N 1.2157(10) 0.5027(8) 0.7820(6) 0.0224(16) Uani 1 1 d . . . . .
H1A H 1.184842 0.437881 0.802635 0.027 Uiso 1 1 calc R . . . .
N2A N 0.9944(11) 0.3922(8) 0.5963(6) 0.0215(16) Uani 1 1 d . . . . .
H2AA H 0.937361 0.385065 0.523211 0.026 Uiso 1 1 calc R . . . .
H2AB H 0.964660 0.329775 0.620283 0.026 Uiso 1 1 calc R . . . .
N3A N 1.1726(10) 0.5929(8) 0.6354(7) 0.0197(15) Uani 1 1 d . . . . .
C5A C 1.4021(13) 0.7100(10) 0.8308(8) 0.023(2) Uani 1 1 d . . . . .
H5A H 1.495214 0.785082 0.884841 0.028 Uiso 1 1 calc R . . . .
N2B N 1.0012(14) -0.0306(10) 0.7279(10) 0.039(2) Uani 1 1 d . . . . .
H2BA H 0.941085 -0.039941 0.654804 0.047 Uiso 1 1 calc R . . . .
H2BB H 1.087577 0.039850 0.774871 0.047 Uiso 1 1 calc R . . . .
N1B N 0.8308(11) -0.2299(9) 0.6965(8) 0.0282(19) Uani 1 1 d . . . . .
H1B H 0.771300 -0.238500 0.623483 0.034 Uiso 1 1 calc R . . . .
C6A C 1.3504(12) 0.6061(11) 0.8595(8) 0.024(2) Uani 1 1 d . . . . .
H6A H 1.411217 0.607717 0.935679 0.029 Uiso 1 1 calc R . . . .
C4A C 1.3039(13) 0.6947(10) 0.7135(8) 0.0220(19) Uani 1 1 d . . . . .
H4A H 1.334859 0.763263 0.688941 0.026 Uiso 1 1 calc R . . . .
N3B N 1.0615(12) -0.1052(9) 0.8787(7) 0.030(2) Uani 1 1 d . . . . .
C2A C 1.1256(12) 0.4971(9) 0.6704(7) 0.0173(17) Uani 1 1 d . . . . .
C2B C 0.9621(14) -0.1219(12) 0.7669(9) 0.028(2) Uani 1 1 d . . . . .
C6B C 0.7865(15) -0.3258(11) 0.7330(11) 0.031(2) Uani 1 1 d . . . . .
H6B H 0.693590 -0.401874 0.681611 0.037 Uiso 1 1 calc R . . . .
C4B C 1.0193(17) -0.1967(12) 0.9162(10) 0.037(3) Uani 1 1 d . . . . .
H4B H 1.086737 -0.185916 0.994567 0.045 Uiso 1 1 calc R . . . .
C5B C 0.8822(17) -0.3087(13) 0.8487(11) 0.038(3) Uani 1 1 d . . . . .
H5B H 0.854977 -0.371571 0.880897 0.045 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'
Bi Bi -4.1077 10.2566 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 1 -1 0.0192
-1 -1 1 0.0192
0 -1 0 0.0483
0 1 0 0.0483
0 0 1 0.0979
0 0 -1 0.1449
3 -5 2 0.0968
-2 5 -3 0.1150
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
Br5 Bi Br3 176.79(3) . . ?
Br5 Bi Br3 91.11(3) . 2_656 ?
Br5 Bi Br4 91.52(3) . . ?
Br3 Bi Br3 85.68(3) . 2_656 ?
Br3 Bi Br4 88.58(3) . . ?
Br4 Bi Br3 89.10(3) . 2_656 ?
Br1 Bi Br5 95.09(3) . . ?
Br1 Bi Br3 173.77(3) . 2_656 ?
Br1 Bi Br3 88.12(3) . . ?
Br1 Bi Br4 90.16(3) . . ?
Br1 Bi Br2 90.44(3) . . ?
Br2 Bi Br5 87.25(3) . . ?
Br2 Bi Br3 90.44(3) . 2_656 ?
Br2 Bi Br3 92.62(3) . . ?
Br2 Bi Br4 178.67(3) . . ?
Bi Br3 Bi 94.32(3) . 2_656 ?
C6A N1A H1A 119.7 . . ?
C6A N1A C2A 120.6(8) . . ?
C2A N1A H1A 119.7 . . ?
H2AA N2A H2AB 120.0 . . ?
C2A N2A H2AA 120.0 . . ?
C2A N2A H2AB 120.0 . . ?
C4A N3A C2A 117.8(8) . . ?
C6A C5A H5A 123.0 . . ?
C6A C5A C4A 114.0(8) . . ?
C4A C5A H5A 123.0 . . ?
H2BA N2B H2BB 120.0 . . ?
C2B N2B H2BA 120.0 . . ?
C2B N2B H2BB 120.0 . . ?
C2B N1B H1B 118.7 . . ?
C2B N1B C6B 122.6(9) . . ?
C6B N1B H1B 118.7 . . ?
N1A C6A C5A 121.4(8) . . ?
N1A C6A H6A 119.3 . . ?
C5A C6A H6A 119.3 . . ?
N3A C4A C5A 125.4(9) . . ?
N3A C4A H4A 117.3 . . ?
C5A C4A H4A 117.3 . . ?
C4B N3B C2B 116.9(10) . . ?
N2A C2A N1A 118.4(8) . . ?
N2A C2A N3A 120.8(8) . . ?
N3A C2A N1A 120.8(8) . . ?
N2B C2B N1B 120.8(10) . . ?
N2B C2B N3B 118.0(10) . . ?
N1B C2B N3B 121.2(10) . . ?
N1B C6B H6B 121.4 . . ?
N1B C6B C5B 117.2(11) . . ?
C5B C6B H6B 121.4 . . ?
N3B C4B H4B 117.9 . . ?
N3B C4B C5B 124.2(11) . . ?
C5B C4B H4B 117.9 . . ?
C6B C5B C4B 117.8(10) . . ?
C6B C5B H5B 121.1 . . ?
C4B C5B H5B 121.1 . . ?
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
Bi Br5 2.8246(9) . ?
Bi Br3 3.0902(10) 2_656 ?
Bi Br3 2.9361(9) . ?
Bi Br4 2.9644(10) . ?
Bi Br1 2.7247(9) . ?
Bi Br2 2.7333(10) . ?
N1A H1A 0.8800 . ?
N1A C6A 1.344(13) . ?
N1A C2A 1.379(11) . ?
N2A H2AA 0.8800 . ?
N2A H2AB 0.8800 . ?
N2A C2A 1.330(11) . ?
N3A C4A 1.322(12) . ?
N3A C2A 1.338(11) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.382(14) . ?
C5A C4A 1.416(12) . ?
N2B H2BA 0.8800 . ?
N2B H2BB 0.8800 . ?
N2B C2B 1.314(14) . ?
N1B H1B 0.8800 . ?
N1B C2B 1.342(14) . ?
N1B C6B 1.348(14) . ?
C6A H6A 0.9500 . ?
C4A H4A 0.9500 . ?
N3B C2B 1.360(13) . ?
N3B C4B 1.309(15) . ?
C6B H6B 0.9500 . ?
C6B C5B 1.384(16) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.389(18) . ?
C5B H5B 0.9500 . ?
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
_geom_hbond_publ_flag
N1A H1A Br5 0.88 2.49 3.241(9) 143.7 1_655 yes
N2A H2AA N3A 0.88 2.08 2.949(10) 168.8 2_766 yes
N2A H2AB Br3 0.88 2.92 3.646(8) 140.8 . yes
N2B H2BA Br3 0.88 2.69 3.487(10) 152.0 . yes
N2B H2BB Br5 0.88 2.60 3.440(11) 160.7 1_655 yes
N1B H1B Br4 0.88 2.48 3.291(8) 154.3 2_656 yes
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 1.0000 -1.0000 -0.0332 0.0634 0.0962
-1.0000 -1.0000 1.0000 0.0332 -0.0634 -0.0962
0.0000 -1.0000 -0.0000 0.0588 -0.0396 0.0021
-0.0000 1.0000 0.0000 -0.0588 0.0396 -0.0021
0.0000 0.0000 1.0000 -0.0598 -0.0325 -0.0122
-0.0000 -0.0000 -1.0000 0.0598 0.0325 0.0122
3.0000 -5.0000 2.0000 0.0717 -0.2889 0.2443
-2.0000 5.0000 -3.0000 -0.0461 0.3127 -0.1460
