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#$Date: 2016-03-24 14:08:23 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179653 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/06/4510698.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_4510698
loop_
_publ_author_name
'Olejniczak, Anna'
'Anioła, Michalina'
'Szafrański, Marek'
'Budzianowski, Armand'
'Katrusiak, Andrzej'
_publ_section_title
;
 New Polar Phases of 1,4-Diazabicyclo[2.2.2]octane Perchlorate, An
 NH+···N Hydrogen-Bonded Ferroelectric
;
_journal_issue                   7
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2872
_journal_paper_doi               10.1021/cg400276c
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C6 H13 N2, Cl O4'
_chemical_formula_sum            'C6 H13 Cl N2 O4'
_chemical_formula_weight         212.63
_chemical_name_common
;
dabcoHClO4
;
_chemical_name_systematic
; 
1,4-diazabicyclo[2.2.2]octane perchlorate
;
_space_group_IT_number           31
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P -2ab -2'
_symmetry_space_group_name_H-M   'P m 21 n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.8779(8)
_cell_length_b                   9.7606(11)
_cell_length_c                   5.3422(5)
_cell_measurement_reflns_used    2089
_cell_measurement_temperature    222.5(2)
_cell_measurement_theta_max      29.02
_cell_measurement_theta_min      3.81
_cell_volume                     462.92(8)
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_molecular_graphics
;X-Seed (Barbour, 2001) 
and POV-Ray (Persistence of Vision, 2004)
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      222.5(2)
_diffrn_measured_fraction_theta_full 0.939
_diffrn_measured_fraction_theta_max 0.939
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            2089
_diffrn_reflns_theta_full        29.02
_diffrn_reflns_theta_max         29.02
_diffrn_reflns_theta_min         3.81
_exptl_absorpt_coefficient_mu    0.399
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (1990)).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.13(11)
_refine_ls_extinction_coef       0.036(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     71
_refine_ls_number_reflns         1004
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0672P)²+0.0941P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0957
_reflns_number_gt                966
_reflns_number_total             1004
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400276c_si_002.cif
_cod_data_source_block           dabcoHClO4_II_222.5K
_cod_original_sg_symbol_H-M      Pm21n
_cod_database_code               4510698
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl Cl 0.0000 -0.01755(10) -0.06976(11) 0.0319(2) Uani 1 2 d S
O1 O 0.0000 -0.0200(8) -0.3375(4) 0.0693(8) Uani 1 2 d S
O2 O 0.1333(2) -0.0873(3) 0.0174(4) 0.0537(6) Uani 1 1 d .
O3 O 0.0000 0.1198(3) 0.0206(7) 0.0647(9) Uani 1 2 d S
N2 N 0.0000 0.5495(4) 0.2795(5) 0.0344(6) Uani 1 2 d S
N1 N 0.0000 0.5480(3) 0.7521(5) 0.0370(6) Uani 1 2 d S
H1 H 0.0000 0.5483 0.9225 0.044 Uiso 1 2 calc SR
C2 C 0.0000 0.4098(5) 0.3700(8) 0.081(2) Uani 1 2 d S
H2A H 0.0884 0.3627 0.3068 0.097 Uiso 0.50 1 calc PR
H2B H -0.0884 0.3627 0.3068 0.097 Uiso 0.50 1 calc PR
C1 C 0.0000 0.4038(5) 0.6623(6) 0.0496(11) Uani 1 2 d S
H1A H -0.0887 0.3560 0.7223 0.059 Uiso 0.50 1 calc PR
H1B H 0.0887 0.3560 0.7223 0.059 Uiso 0.50 1 calc PR
C4 C 0.1344(3) 0.6205(4) 0.3771(5) 0.0577(9) Uani 1 1 d .
H4A H 0.1347 0.7143 0.3173 0.069 Uiso 1 1 calc R
H4B H 0.2241 0.5757 0.3133 0.069 Uiso 1 1 calc R
C3 C 0.1393(3) 0.6207(3) 0.6594(5) 0.0429(6) Uani 1 1 d .
H3A H 0.1414 0.7140 0.7217 0.051 Uiso 1 1 calc R
H3B H 0.2289 0.5737 0.7178 0.051 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
O3 Cl O1 110.8(4) . .
O3 Cl O2 109.54(13) . .
O1 Cl O2 108.36(18) . .
O3 Cl O2 109.54(13) . 4
O1 Cl O2 108.36(18) . 4
O2 Cl O2 110.2(2) . 4
C2 N2 C4 108.9(2) . .
C2 N2 C4 108.9(2) . 4
C4 N2 C4 108.0(3) . 4
C1 N1 C3 109.81(18) . .
C1 N1 C3 109.81(18) . 4
C3 N1 C3 110.0(3) . 4
C1 N1 H1 109.1 . .
C3 N1 H1 109.1 . .
C3 N1 H1 109.1 4 .
N2 C2 C1 111.7(3) . .
N2 C2 H2A 109.3 . .
C1 C2 H2A 109.3 . .
N2 C2 H2B 109.3 . .
C1 C2 H2B 109.3 . .
H2A C2 H2B 107.9 . .
N1 C1 C2 106.7(3) . .
N1 C1 H1A 110.4 . .
C2 C1 H1A 110.4 . .
N1 C1 H1B 110.4 . .
C2 C1 H1B 110.4 . .
H1A C1 H1B 108.6 . .
N2 C4 C3 112.1(2) . .
N2 C4 H4A 109.2 . .
C3 C4 H4A 109.2 . .
N2 C4 H4B 109.2 . .
C3 C4 H4B 109.2 . .
H4A C4 H4B 107.9 . .
C4 C3 N1 107.73(19) . .
C4 C3 H3A 110.2 . .
N1 C3 H3A 110.2 . .
C4 C3 H3B 110.2 . .
N1 C3 H3B 110.2 . .
H3A C3 H3B 108.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl O3 1.425(3) .
Cl O1 1.430(2) .
Cl O2 1.4422(19) .
Cl O2 1.4422(19) 4
N2 C2 1.447(5) .
N2 C4 1.475(3) .
N2 C4 1.475(3) 4
N1 C1 1.487(5) .
N1 C3 1.509(3) .
N1 C3 1.509(3) 4
N1 H1 0.9100 .
C2 C1 1.562(5) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C1 H1A 0.9700 .
C1 H1B 0.9700 .
C4 C3 1.508(3) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
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_1
C4 N2 C2 C1 58.80(16) .
C4 N2 C2 C1 -58.80(16) 4
C3 N1 C1 C2 -60.54(15) .
C3 N1 C1 C2 60.54(15) 4
N2 C2 C1 N1 0.000(1) .
C2 N2 C4 C3 -58.7(3) .
C4 N2 C4 C3 59.5(4) 4
N2 C4 C3 N1 -0.8(4) .
C1 N1 C3 C4 61.5(3) .
C3 N1 C3 C4 -59.4(4) 4
