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#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/07/4510706.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_4510706
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           33
_symmetry_space_group_name_Hall  'P -2n -2ac'
_symmetry_space_group_name_H-M   'P c 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            4
_cell_length_a                   8.496(4)
_cell_length_b                   9.4293(16)
_cell_length_c                   10.6475(13)
_cell_measurement_pressure       1000000
_cell_measurement_reflns_used    4453
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.29
_cell_measurement_theta_min      3.83
_cell_volume                     853.0(4)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.290
_diffrn_measured_fraction_theta_max 0.290
_diffrn_measurement_device_type  'Kuma KM4CCD κ geometry'
_diffrn_measurement_method
;HP omega scans - for more details see:
A. Budzianowski, A. Katrusiak in High-Pressure Crystallography
(Eds.: A. Katrusiak, P. F. McMillan),
Dordrecht: Kluwer Acad. Publ., 2004 pp.157-168
;
_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  0.0939
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4453
_diffrn_reflns_theta_full        29.29
_diffrn_reflns_theta_max         29.29
_diffrn_reflns_theta_min         3.83
_exptl_absorpt_coefficient_mu    0.433
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_correction_T_min  0.41
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Katrusiak, A. (2003). REDSHABS - Program for correcting
reflections intensities for DAC absorption, gasket shadowing
and sample crystal absorption. Adam Mickiewicz University, Poznań.
Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(4)
_refine_ls_extinction_coef       0.004(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     59
_refine_ls_number_reflns         681
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.1005
_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)+(0.0813P)²+4.1501P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2092
_refine_ls_wR_factor_ref         0.2142
_reflns_number_gt                629
_reflns_number_total             681
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400276c_si_002.cif
_cod_data_source_block           dabcoHClO4_III_1.0GPa
_cod_original_cell_volume        852.9(4)
_cod_original_sg_symbol_Hall     'P 2c -2ac'
_cod_database_code               4510706
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x+1/2, y, z+1/2'
'x+1/2, y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.7520(9) 0.3141(4) 0.7166(2) 0.022(3) Uani 1 1 d .
O2 O 0.738(3) 0.4493(11) 0.7609(10) 0.044(3) Uiso 1 1 d .
O3 O 0.631(4) 0.2190(12) 0.7711(11) 0.063(4) Uiso 1 1 d .
O1 O 0.738(3) 0.3284(15) 0.5837(8) 0.051(3) Uiso 1 1 d .
O4 O 0.895(4) 0.2577(11) 0.7481(8) 0.037(3) Uiso 1 1 d .
N2 N 0.290(3) 0.3784(9) 0.3733(9) 0.020(2) Uiso 1 1 d .
C1 C 0.233(4) 0.2373(14) 0.5630(12) 0.037(4) Uiso 1 1 d .
H1A H 0.1221 0.2115 0.5630 0.045 Uiso 1 1 calc R
H1B H 0.2889 0.1721 0.6173 0.045 Uiso 1 1 calc R
N1 N 0.252(3) 0.3823(10) 0.6072(10) 0.027(3) Uiso 1 1 d .
H1N H 0.2373 0.3852 0.6918 0.032 Uiso 1 1 calc R
C4 C 0.131(4) 0.4367(11) 0.3972(9) 0.012(2) Uiso 1 1 d .
H4A H 0.0520 0.3756 0.3604 0.014 Uiso 1 1 calc R
H4B H 0.1217 0.5302 0.3601 0.014 Uiso 1 1 calc R
C5 C 0.369(5) 0.4597(16) 0.5784(12) 0.047(4) Uiso 1 1 d .
H5A H 0.4624 0.4259 0.6210 0.056 Uiso 1 1 calc R
H5B H 0.3491 0.5565 0.6050 0.056 Uiso 1 1 calc R
C6 C 0.393(3) 0.4553(10) 0.4393(8) 0.014(2) Uiso 1 1 d .
H6A H 0.3905 0.5518 0.4079 0.016 Uiso 1 1 calc R
H6B H 0.4979 0.4184 0.4233 0.016 Uiso 1 1 calc R
C2 C 0.301(4) 0.2304(13) 0.4253(11) 0.035(4) Uiso 1 1 d .
H2A H 0.4095 0.1985 0.4266 0.042 Uiso 1 1 calc R
H2B H 0.2399 0.1653 0.3743 0.042 Uiso 1 1 calc R
C3 C 0.108(6) 0.446(2) 0.5410(15) 0.072(6) Uiso 1 1 d .
H3A H 0.0949 0.5437 0.5660 0.087 Uiso 1 1 calc R
H3B H 0.0144 0.3937 0.5650 0.087 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
O2 Cl1 O4 110.7(11)
O2 Cl1 O1 104.3(7)
O4 Cl1 O1 110.7(12)
O2 Cl1 O3 111.8(11)
O4 Cl1 O3 106.7(12)
O1 Cl1 O3 112.7(12)
C6 N2 C4 107.8(12)
C6 N2 C2 105.7(15)
C4 N2 C2 110(2)
N1 C1 C2 107.3(14)
N1 C1 H1A 110.3
C2 C1 H1A 110.3
N1 C1 H1B 110.3
C2 C1 H1B 110.3
H1A C1 H1B 108.5
C5 N1 C1 124(2)
C5 N1 C3 106.7(17)
C1 N1 C3 97.2(19)
C5 N1 H1N 109.4
C1 N1 H1N 109.4
C3 N1 H1N 109.4
N2 C4 C3 108(2)
N2 C4 H4A 110.1
C3 C4 H4A 110.1
N2 C4 H4B 110.1
C3 C4 H4B 110.1
H4A C4 H4B 108.5
N1 C5 C6 109(2)
N1 C5 H5A 109.8
C6 C5 H5A 109.8
N1 C5 H5B 109.8
C6 C5 H5B 109.8
H5A C5 H5B 108.2
N2 C6 C5 116(2)
N2 C6 H6A 108.2
C5 C6 H6A 108.2
N2 C6 H6B 108.2
C5 C6 H6B 108.2
H6A C6 H6B 107.3
N2 C2 C1 106.4(13)
N2 C2 H2A 110.5
C1 C2 H2A 110.5
N2 C2 H2B 110.5
C1 C2 H2B 110.5
H2A C2 H2B 108.6
N1 C3 C4 109(3)
N1 C3 H3A 109.8
C4 C3 H3A 109.8
N1 C3 H3B 109.8
C4 C3 H3B 109.8
H3A C3 H3B 108.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 O2 1.365(11)
Cl1 O4 1.37(3)
Cl1 O1 1.427(9)
Cl1 O3 1.48(2)
N2 C6 1.34(3)
N2 C4 1.48(4)
N2 C2 1.504(16)
C1 N1 1.456(15)
C1 C2 1.58(2)
C1 H1A 0.9700
C1 H1B 0.9700
N1 C5 1.27(4)
N1 C3 1.53(4)
N1 H1N 0.9100
C4 C3 1.545(19)
C4 H4A 0.9700
C4 H4B 0.9700
C5 C6 1.497(16)
C5 H5A 0.9700
C5 H5B 0.9700
C6 H6A 0.9700
C6 H6B 0.9700
C2 H2A 0.9700
C2 H2B 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
C2 C1 N1 C5 -35(3)
C2 C1 N1 C3 81(3)
C6 N2 C4 C3 -51.8(18)
C2 N2 C4 C3 62.8(19)
C1 N1 C5 C6 49(3)
C3 N1 C5 C6 -62(2)
C4 N2 C6 C5 58.7(19)
C2 N2 C6 C5 -58(2)
N1 C5 C6 N2 2(3)
C6 N2 C2 C1 68(3)
C4 N2 C2 C1 -48(3)
N1 C1 C2 N2 -25(4)
C5 N1 C3 C4 63(2)
C1 N1 C3 C4 -65(2)
N2 C4 C3 N1 -4(3)
