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#$Date: 2024-03-07 05:07:01 +0200 (Thu, 07 Mar 2024) $
#$Revision: 290375 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/11/1571165.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1571165
loop_
_publ_author_name
'Budzianowski, Armand'
'Petřiček, Vaclav'
'Katrusiak, Andrzej'
_publ_section_title
;
 Metal-free enantiomorphic perovskite
 [dabcoH₂]²⁺[H₃O]⁺Br⁻
 ₃ and its one-dimensional polar polymorph.
;
_journal_issue                   'Pt 5'
_journal_name_full               IUCrJ
_journal_page_first              544
_journal_page_last               550
_journal_paper_doi               10.1107/S2052252522006406
_journal_volume                  9
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C6 H14 N2, 3 Br, H3 O,'
_chemical_formula_sum            'C6 H17 Br3 N2 O'
_chemical_formula_weight         372.94
_chemical_name_common            'dabco hydronium tri-bromide'
_chemical_name_systematic
;
(1,4-diazabicyclo[2.2.2]octane) hydronium tri-bromide
;
_space_group_crystal_system      trigonal
_space_group_IT_number           158
_space_group_name_Hall           'P 3 -2"c'
_space_group_name_H-M_alt        'P 3 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2022-01-03 deposited with the CCDC. 2022-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   16.04250(10)
_cell_length_b                   16.04250(10)
_cell_length_c                   7.9666(7)
_cell_measurement_reflns_used    15432
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      71.1500
_cell_measurement_theta_min      5.4960
_cell_volume                     1775.61(16)
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.39.25a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_molecular_graphics
;
X-Seed (Barbour, 2020) 
ShelXle (Hubschle et al., 2011)
Persistence of Vision Pty. Ltd. (2004). 
;
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXL-2018/1 (Sheldrick, 2018)'
_diffrn_ambient_temperature      299(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4922
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            37462
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.234
_diffrn_reflns_theta_min         3.181
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    12.368
_exptl_absorpt_correction_T_max  0.334
_exptl_absorpt_correction_T_min  0.060
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
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            'clear colourless'
_exptl_crystal_density_diffrn    2.093
_exptl_crystal_description       plate
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.477
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.144
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
;
 Flack x determined using 934 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_coef       0.00143(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2269
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0287
_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)+(0.0539P)²+0.2214P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0814
_reflns_Friedel_coverage         0.971
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                2033
_reflns_number_total             2269
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ct5016.cif
_cod_data_source_block           dabco1_h168b6_abs2
_cod_database_code               1571165
_shelx_shelxl_version_number     2016/6
_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   0.067
_shelx_estimated_absorpt_t_max   0.269
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'-y, -x, 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
O1W O 0.333333 0.666667 0.6967(16) 0.066(3) Uani 0.834(14) 3 d DS T P A 1
H1W H 0.381(5) 0.664(9) 0.727(9) 0.079 Uiso 0.834(14) 1 d D U P A 1
O2W O 1.000000 1.000000 0.942(3) 0.086(7) Uani 0.51(2) 3 d DS T P B 1
H2W H 0.946(5) 0.985(16) 0.906(12) 0.103 Uiso 0.51(2) 1 d D U P B 1
O1WA O 0.333333 0.666667 0.910(8) 0.066(3) Uani 0.166(14) 3 d DS T P A 2
H1WA H 0.380(19) 0.66(3) 0.879(17) 0.079 Uiso 0.166(14) 1 d D U P A 2
O2WA O 1.000000 1.000000 0.687(2) 0.060(5) Uani 0.49(2) 3 d DS T P B 2
H2WA H 0.951(7) 0.951(7) 0.719(12) 0.072 Uiso 0.49(2) 1 d D U P B 2
Br1 Br 0.52723(5) 0.68784(4) 0.8224(5) 0.0517(5) Uani 1 1 d . . . . .
Br2 Br 0.82726(5) 0.80611(5) 0.8231(5) 0.0522(5) Uani 1 1 d . . . . .
Br3 Br 0.64555(4) 0.50584(4) 0.85219(2) 0.0452(3) Uani 1 1 d . . . . .
O3W O 0.666667 0.333333 0.9623(16) 0.078(3) Uani 1 3 d DS T P . .
H3W H 0.644(7) 0.366(6) 0.917(8) 0.094 Uiso 1 1 d D U . . .
N1 N 0.6640(3) 0.6712(3) 0.4887(8) 0.0378(11) Uani 1 1 d . . . . .
H1 H 0.661536 0.674732 0.611311 0.045 Uiso 1 1 calc R U . . .
N2 N 0.6690(3) 0.6620(3) 0.1785(8) 0.0385(11) Uani 1 1 d . . . . .
H2 H 0.671266 0.658507 0.055929 0.046 Uiso 1 1 calc R U . . .
C1 C 0.7133(5) 0.7713(4) 0.4200(9) 0.0480(13) Uani 1 1 d . . . . .
H1A H 0.778349 0.807337 0.463699 0.058 Uiso 1 1 calc R U . . .
H1B H 0.678756 0.803958 0.452757 0.058 Uiso 1 1 calc R U . . .
C2 C 0.5636(5) 0.6166(5) 0.4237(10) 0.0527(14) Uani 1 1 d . . . . .
H2A H 0.528646 0.649129 0.454940 0.063 Uiso 1 1 calc R U . . .
H2B H 0.530725 0.552524 0.472008 0.063 Uiso 1 1 calc R U . . .
C3 C 0.7188(5) 0.6220(5) 0.4445(7) 0.0432(11) Uani 1 1 d . . . . .
H3A H 0.687836 0.558006 0.493104 0.052 Uiso 1 1 calc R U . . .
H3B H 0.783715 0.658036 0.488639 0.052 Uiso 1 1 calc R U . . .
C4 C 0.7155(5) 0.7647(4) 0.2288(9) 0.0489(13) Uani 1 1 d . . . . .
H4A H 0.681498 0.794306 0.178587 0.059 Uiso 1 1 calc R U . . .
H4B H 0.781525 0.798806 0.189398 0.059 Uiso 1 1 calc R U . . .
C5 C 0.5668(4) 0.6100(5) 0.2326(9) 0.0471(12) Uani 1 1 d . . . . .
H5A H 0.536379 0.543127 0.198198 0.057 Uiso 1 1 calc R U . . .
H5B H 0.532336 0.638739 0.181034 0.057 Uiso 1 1 calc R U . . .
C6 C 0.7217(5) 0.6154(5) 0.2529(7) 0.0435(12) Uani 1 1 d . . . . .
H6A H 0.787920 0.647992 0.214220 0.052 Uiso 1 1 calc R U . . .
H6B H 0.691385 0.548487 0.218507 0.052 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
H1W O1W H1W 112(5) . 3_565 ?
H1W O1W H1W 112(5) . 2_665 ?
H1W O1W H1W 112(5) 3_565 2_665 ?
H2W O2W H2W 109(7) . 3_675 ?
H2W O2W H2W 109(7) . 2_765 ?
H2W O2W H2W 109(7) 3_675 2_765 ?
H1WA O1WA H1WA 111(9) . 3_565 ?
H2WA O2WA H2WA 111(7) . 2_765 ?
H2WA O2WA H2WA 111(7) 3_675 2_765 ?
H3W O3W H3W 103(5) . 2_655 ?
H3W O3W H3W 103(5) . 3_665 ?
H3W O3W H3W 103(5) 2_655 3_665 ?
C3 N1 C2 111.0(4) . . ?
C3 N1 C1 110.3(4) . . ?
C2 N1 C1 109.9(4) . . ?
C3 N1 H1 108.5 . . ?
C2 N1 H1 108.5 . . ?
C1 N1 H1 108.5 . . ?
C5 N2 C4 110.2(4) . . ?
C5 N2 C6 110.2(4) . . ?
C4 N2 C6 110.6(4) . . ?
C5 N2 H2 108.6 . . ?
C4 N2 H2 108.6 . . ?
C6 N2 H2 108.6 . . ?
N1 C1 C4 108.0(5) . . ?
N1 C1 H1A 110.1 . . ?
C4 C1 H1A 110.1 . . ?
N1 C1 H1B 110.1 . . ?
C4 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
N1 C2 C5 108.9(5) . . ?
N1 C2 H2A 109.9 . . ?
C5 C2 H2A 109.9 . . ?
N1 C2 H2B 109.9 . . ?
C5 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
N1 C3 C6 108.7(5) . . ?
N1 C3 H3A 110.0 . . ?
C6 C3 H3A 110.0 . . ?
N1 C3 H3B 110.0 . . ?
C6 C3 H3B 110.0 . . ?
H3A C3 H3B 108.3 . . ?
N2 C4 C1 109.2(5) . . ?
N2 C4 H4A 109.8 . . ?
C1 C4 H4A 109.8 . . ?
N2 C4 H4B 109.8 . . ?
C1 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
N2 C5 C2 108.4(5) . . ?
N2 C5 H5A 110.0 . . ?
C2 C5 H5A 110.0 . . ?
N2 C5 H5B 110.0 . . ?
C2 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
N2 C6 C3 108.3(5) . . ?
N2 C6 H6A 110.0 . . ?
C3 C6 H6A 110.0 . . ?
N2 C6 H6B 110.0 . . ?
C3 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
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
O1W H1W 0.82(2) . ?
O1W H1W 0.82(2) 3_565 ?
O1W H1W 0.83(2) 2_665 ?
O2W H2W 0.83(2) . ?
O2W H2W 0.83(2) 3_675 ?
O2W H2W 0.83(2) 2_765 ?
O1WA H1WA 0.83(2) . ?
O1WA H1WA 0.83(2) 3_565 ?
O1WA H1WA 0.83(2) 2_665 ?
O2WA H2WA 0.83(2) . ?
O2WA H2WA 0.83(2) 3_675 ?
O2WA H2WA 0.83(2) 2_765 ?
O3W H3W 0.84(3) . ?
O3W H3W 0.84(3) 2_655 ?
O3W H3W 0.84(3) 3_665 ?
N1 C3 1.488(7) . ?
N1 C2 1.489(8) . ?
N1 C1 1.494(7) . ?
N1 H1 0.9800 . ?
N2 C5 1.484(7) . ?
N2 C4 1.485(7) . ?
N2 C6 1.503(7) . ?
N2 H2 0.9800 . ?
C1 C4 1.529(8) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C5 1.529(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C6 1.532(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
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
O1W H1W Br1 0.82(2) 2.31(3) 3.121(4) 169(12) .
O2W H2W Br2 0.83(2) 2.6(2) 3.102(8) 119(18) .
O1WA H1WA Br1 0.83(2) 2.23(11) 3.037(15) 165(40) .
O2WA H2WA Br2 0.83(2) 2.33(4) 3.148(6) 171(17) .
O3W H3W Br3 0.84(3) 2.30(5) 3.079(4) 154(9) .
N1 H1 Br1 0.98 2.82 3.541(6) 130.7 .
N1 H1 Br2 0.98 2.96 3.602(7) 124.2 .
N1 H1 Br3 0.98 3.22 3.837(5) 122.2 .
N2 H2 Br1 0.98 3.18 3.787(6) 121.6 1_554
N2 H2 Br2 0.98 3.06 3.734(7) 126.8 1_554
N2 H2 Br3 0.98 2.79 3.497(5) 129.5 1_554
C1 H1A Br2 0.97 2.97 3.598(6) 123.4 .
C1 H1B Br1 0.97 2.95 3.738(7) 139.4 5_564
C2 H2A Br1 0.97 3.00 3.521(7) 115.4 .
C2 H2B Br3 0.97 3.08 3.817(7) 133.9 6_664
C3 H3A Br3 0.97 2.96 3.635(6) 127.5 .
C3 H3B Br2 0.97 3.12 3.840(7) 132.0 4_654
C4 H4A Br1 0.97 3.12 3.838(7) 131.8 5_564
C4 H4B Br2 0.97 3.00 3.593(6) 120.9 1_554
C5 H5A Br3 0.97 3.01 3.781(7) 137.1 6_664
C5 H5B Br1 0.97 2.98 3.665(6) 129.0 1_554
C6 H6A Br2 0.97 2.97 3.751(6) 138.8 4_654
C6 H6B Br3 0.97 3.00 3.553(6) 117.2 1_554
