#------------------------------------------------------------------------------
#$Date: 2019-07-31 07:41:19 +0300 (Wed, 31 Jul 2019) $
#$Revision: 217323 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/30/2243037.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_2243037
loop_
_publ_author_name
'Ferrandin, Sarah'
'Slawin, Alexandra M. Z.'
'Harrison, William T. A.'
_publ_section_title
;
 Syntheses and crystal structures of a new family of hybrid perovskites:
 C₅H₁₄N₂·ABr₃·0.5H₂O (A = K, Rb, Cs)
;
_journal_coeditor_code           VN2151
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1243
_journal_page_last               1248
_journal_paper_doi               10.1107/S2056989019010338
_journal_volume                  75
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_iupac          '(C5 H14 N2) [Cs Br3], 0.5H2 O'
_chemical_formula_moiety         'C5 H14 N2, Cs Br3, 0.5(H2 O)'
_chemical_formula_sum            'C5 H15 Br3 Cs N2 O0.5'
_chemical_formula_weight         483.83
_chemical_name_systematic
;
Poly[1-methylpiperizine-1,4-diium [tri-μ-bromido-caesium] hemihydrate]
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           38
_space_group_name_Hall           'A 2 -2'
_space_group_name_H-M_alt        'A m m 2'
_symmetry_space_group_name_Hall  'A 2 -2'
_symmetry_space_group_name_H-M   'A m m 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.610(3)
_cell_length_b                   9.7201(19)
_cell_length_c                   9.977(2)
_cell_measurement_reflns_used    2407
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.9
_cell_volume                     1319.9(5)
_computing_cell_refinement
;
CrysalisPro (Rigaku, 2017)
;
_computing_data_collection
;
CrysalisPro (Rigaku, 2017)
;
_computing_data_reduction
;
CrysalisPro (Rigaku, 2017)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014/7 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS-7 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      93(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Pilatus 200K CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3718
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.355
_diffrn_reflns_theta_min         2.926
_exptl_absorpt_coefficient_mu    11.850
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysalisPro; Rigaku, 2017)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.435
_exptl_crystal_description       block
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.700
_refine_ls_abs_structure_details
;
Parsons et al. (2013)
;
_refine_ls_abs_structure_Flack   0.016(7)
_refine_ls_extinction_coef       0.00081(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2014/7 (Sheldrick 2015)
;
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     68
_refine_ls_number_reflns         1312
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.940
_refine_ls_R_factor_all          0.0136
_refine_ls_R_factor_gt           0.0134
_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)+(0.0012P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0288
_refine_ls_wR_factor_ref         0.0289
_reflns_number_gt                1293
_reflns_number_total             1312
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vn2151sup1.cif
_cod_data_source_block           III
_cod_database_code               2243037
_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   0.384
_shelx_estimated_absorpt_t_max   0.384
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, z'
'x, -y, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, z+1/2'
'x, -y+1/2, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Cs Cs1 0.0000 0.5000 0.10292(5) 0.01104(16) Uani d 1
Cs Cs2 0.5000 0.5000 -0.04771(5) 0.01285(16) Uani d 1
Br Br1 0.0000 0.30234(7) 0.40657(7) 0.01341(18) Uani d 1
Br Br2 0.5000 0.26080(7) 0.21347(7) 0.01513(17) Uani d 1
Br Br3 0.25365(6) 0.5000 0.03902(7) 0.01354(16) Uani d 1
C C1 0.2714(4) 0.6276(5) 0.3848(5) 0.0140(11) Uani d 1
H H1A 0.2128 0.6348 0.3263 0.017 Uiso calc 1
H H1B 0.3132 0.7093 0.3686 0.017 Uiso calc 1
C C2 0.2391(4) 0.6259(4) 0.5301(6) 0.0138(10) Uani d 1
H H2A 0.2977 0.6263 0.5890 0.017 Uiso calc 1
H H2B 0.2001 0.7095 0.5497 0.017 Uiso calc 1
C C3 0.1412(5) 0.5000 0.6985(7) 0.0189(16) Uani d 1
H H3A 0.1014 0.4149 0.7140 0.028 Uiso d 1
H H3B 0.1974 0.5000 0.7625 0.028 Uiso d 1
N N1 0.3276(4) 0.5000 0.3497(6) 0.0125(13) Uani d 1
H H1N 0.3408 0.5000 0.2603 0.015 Uiso calc 1
H H2N 0.3859 0.5000 0.3944 0.015 Uiso calc 1
N N2 0.1782(4) 0.5000 0.5586(6) 0.0112(12) Uani d 1
H H3N 0.1205 0.5000 0.4965 0.013 Uiso calc 1
O O1 0.5000 0.5000 0.5110(6) 0.0149(16) Uani d 1
H H1O 0.5000 0.5749 0.5620 0.018 Uiso d 1
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'
Cs Cs -0.3680 2.1192 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Br3 Cs1 Br3 2_565 . 159.07(3) ?
Br3 Cs1 Br1 2_565 6_554 84.218(9) ?
Br3 Cs1 Br1 . 6_554 84.219(9) ?
Br3 Cs1 Br1 2_565 5_554 84.218(9) ?
Br3 Cs1 Br1 . 5_554 84.219(9) ?
Br1 Cs1 Br1 6_554 5_554 112.63(3) ?
Br3 Cs1 Br1 2_565 2_565 98.823(12) ?
Br3 Cs1 Br1 . 2_565 98.822(12) ?
Br1 Cs1 Br1 6_554 2_565 156.07(2) ?
Br1 Cs1 Br1 5_554 2_565 91.305(15) ?
Br3 Cs1 Br1 2_565 . 98.823(12) ?
Br3 Cs1 Br1 . . 98.822(13) ?
Br1 Cs1 Br1 6_554 . 91.305(15) ?
Br1 Cs1 Br1 5_554 . 156.07(2) ?
Br1 Cs1 Br1 2_565 . 64.76(3) ?
Br3 Cs2 Br3 . 2_665 151.06(3) ?
Br3 Cs2 Br2 . 6_654 99.854(11) ?
Br3 Cs2 Br2 2_665 6_654 99.854(11) ?
Br3 Cs2 Br2 . 5_554 99.854(11) ?
Br3 Cs2 Br2 2_665 5_554 99.854(11) ?
Br2 Cs2 Br2 6_654 5_554 93.55(3) ?
Br3 Cs2 Br2 . 2_665 79.254(13) ?
Br3 Cs2 Br2 2_665 2_665 79.255(13) ?
Br2 Cs2 Br2 6_654 2_665 174.97(3) ?
Br2 Cs2 Br2 5_554 2_665 91.485(16) ?
Br3 Cs2 Br2 . . 79.254(13) ?
Br3 Cs2 Br2 2_665 . 79.255(13) ?
Br2 Cs2 Br2 6_654 . 91.485(16) ?
Br2 Cs2 Br2 5_554 . 174.97(3) ?
Br2 Cs2 Br2 2_665 . 83.48(3) ?
Cs1 Br1 Cs1 5_545 . 156.07(2) y
Cs2 Br2 Cs2 5_545 . 174.97(3) y
Cs2 Br3 Cs1 . . 175.99(3) y
N1 C1 C2 . . 111.3(4) ?
N1 C1 H1A . . 109.4 ?
C2 C1 H1A . . 109.4 ?
N1 C1 H1B . . 109.4 ?
C2 C1 H1B . . 109.4 ?
H1A C1 H1B . . 108.0 ?
N2 C2 C1 . . 110.4(4) ?
N2 C2 H2A . . 109.6 ?
C1 C2 H2A . . 109.6 ?
N2 C2 H2B . . 109.6 ?
C1 C2 H2B . . 109.6 ?
H2A C2 H2B . . 108.1 ?
N2 C3 H3A . . 109.2 ?
N2 C3 H3B . . 110.0 ?
H3A C3 H3B . . 108.5 ?
C1 N1 C1 4_565 . 111.7(5) ?
C1 N1 H1N 4_565 . 109.3 ?
C1 N1 H1N . . 109.3 ?
C1 N1 H2N 4_565 . 109.3 ?
C1 N1 H2N . . 109.3 ?
H1N N1 H2N . . 107.9 ?
C3 N2 C2 . . 111.4(4) ?
C3 N2 C2 . 4_565 111.4(4) ?
C2 N2 C2 . 4_565 108.8(5) ?
C3 N2 H3N . . 108.4 ?
C2 N2 H3N . . 108.4 ?
C2 N2 H3N 4_565 . 108.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cs1 Br1 6_554 3.5319(9) y
Cs1 Br1 5_554 3.5319(9) ?
Cs1 Br1 2_565 3.5873(10) ?
Cs1 Br1 . 3.5873(10) y
Cs1 Br3 2_565 3.5105(11) ?
Cs1 Br3 . 3.5105(11) y
Cs2 Br2 2_665 3.4923(10) ?
Cs2 Br2 . 3.4923(10) y
Cs2 Br2 6_654 3.4790(9) y
Cs2 Br2 5_554 3.4790(9) ?
Cs2 Br3 . 3.4627(11) y
Cs2 Br3 2_665 3.4627(11) ?
Br1 Cs1 5_545 3.5319(9) ?
Br2 Cs2 5_545 3.4790(9) ?
C1 N1 . 1.499(6) ?
C1 C2 . 1.515(7) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 N2 . 1.505(6) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 N2 . 1.484(9) ?
C3 H3A . 1.0011 ?
C3 H3B . 0.9961 ?
N1 C1 4_565 1.499(6) ?
N1 H1N . 0.9100 ?
N1 H2N . 0.9100 ?
N2 C2 4_565 1.505(6) ?
N2 H3N . 1.0000 ?
O1 H1O . 0.8883 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H2N O1 . 0.91 1.94 2.845(7) 173
N1 H1N Br3 . 0.91 2.51 3.259(6) 140
N2 H3N Br1 . 1.00 2.68 3.446(5) 134
N2 H3N Br1 2_565 1.00 2.68 3.446(5) 134
O1 H1O Br2 5 0.89 2.36 3.242(4) 175
C1 H1A Br1 2_565 0.99 3.07 3.762(5) 128
C1 H1B Br2 2_665 0.99 2.99 3.712(5) 131
C2 H2B Br1 2_565 0.99 3.08 3.550(5) 111
C2 H2B Br3 5 0.99 2.92 3.643(4) 131
C3 H3B Br3 1_556 1.00 2.86 3.726(7) 145
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_site_symmetry_4
_geom_torsion
N1 C1 C2 N2 . -57.1(6)
C2 C1 N1 C1 4_565 53.6(7)
C1 C2 N2 C3 . -176.9(4)
C1 C2 N2 C2 4_565 60.0(7)

_cod_database_fobs_code 2243037
