#------------------------------------------------------------------------------
#$Date: 2016-03-05 11:11:06 +0200 (Sat, 05 Mar 2016) $
#$Revision: 177760 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/40/7224043.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_7224043
loop_
_publ_author_name
'Han, Xiang-Bin'
'Hu, Pan'
'Shi, Chao'
'Zhang, Wen'
_publ_section_title
;
 1,4-Diazabicyclo[2.2.2]octane-based disalts showing non-centrosymmetric
 structures and phase transition behaviors
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              1563
_journal_paper_doi               10.1039/C5CE02066B
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C6 H14 N2, 2(Cl O4), H2 O'
_chemical_formula_sum            'C6 H16 Cl2 N2 O9'
_chemical_formula_weight         331.11
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-12-26 deposited with the CCDC.
2016-01-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.296(10)
_cell_length_b                   8.069(6)
_cell_length_c                   11.772(9)
_cell_measurement_reflns_used    8501
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.450
_cell_measurement_theta_min      3.461
_cell_volume                     1263.0(16)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_laue_measured_fraction_full 0.986
_diffrn_reflns_laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8501
_diffrn_reflns_point_group_measured_fraction_full 0.797
_diffrn_reflns_point_group_measured_fraction_max 0.771
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.450
_diffrn_reflns_theta_min         3.461
_exptl_absorpt_coefficient_mu    0.560
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 636 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(7)
_refine_ls_extinction_coef       0.010(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2222
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.172
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0553
_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)+(0.0232P)²+2.9545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1270
_reflns_Friedel_coverage         0.503
_reflns_friedel_fraction_full    0.587
_reflns_friedel_fraction_max     0.544
_reflns_number_gt                2163
_reflns_number_total             2879
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ce02066b2.cif
_cod_data_source_block           233
_cod_depositor_comments
'Adding full bibliography for 7224040--7224043.cif.'
_cod_database_code               7224043
_shelx_shelxl_version_number     2014/7
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -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
C1 C 0.6051(7) 0.8537(10) 0.6857(6) 0.043(2) Uani 1 1 d . .
H1A H 0.6618 0.8217 0.7327 0.052 Uiso 1 1 calc R U
H1B H 0.5606 0.9225 0.7307 0.052 Uiso 1 1 calc R U
C2 C 0.6418(6) 0.9495(8) 0.5829(6) 0.0384(16) Uani 1 1 d . .
H2A H 0.6133 1.0601 0.5832 0.046 Uiso 1 1 calc R U
H2B H 0.7145 0.9595 0.5853 0.046 Uiso 1 1 calc R U
C3 C 0.6178(8) 0.5959(10) 0.5773(8) 0.060(3) Uani 1 1 d . .
H3A H 0.5815 0.4978 0.5530 0.072 Uiso 1 1 calc R U
H3B H 0.6741 0.5606 0.6236 0.072 Uiso 1 1 calc R U
C4 C 0.6559(5) 0.6870(8) 0.4756(7) 0.0353(15) Uani 1 1 d . .
H4A H 0.6362 0.6296 0.4066 0.042 Uiso 1 1 calc R U
H4B H 0.7287 0.6934 0.4777 0.042 Uiso 1 1 calc R U
C5 C 0.4641(6) 0.7573(11) 0.5758(7) 0.048(2) Uani 1 1 d . .
H5A H 0.4215 0.8299 0.6205 0.058 Uiso 1 1 calc R U
H5B H 0.4246 0.6616 0.5535 0.058 Uiso 1 1 calc R U
C6 C 0.4994(5) 0.8467(9) 0.4723(7) 0.0372(15) Uani 1 1 d . .
H6A H 0.4793 0.7865 0.4047 0.045 Uiso 1 1 calc R U
H6B H 0.4696 0.9564 0.4694 0.045 Uiso 1 1 calc R U
Cl1 Cl 0.77285(11) 0.22100(17) 0.84186(13) 0.0293(4) Uani 1 1 d . .
Cl2 Cl 0.91119(11) 0.74147(17) 0.65756(15) 0.0289(4) Uani 1 1 d . .
H1WA H 0.608(4) 0.483(7) 0.875(6) 0.043 Uiso 1 1 d D U
H1WB H 0.561(6) 0.627(7) 0.908(5) 0.043 Uiso 1 1 d D U
N1 N 0.6108(4) 0.8599(6) 0.4774(5) 0.0267(11) Uani 1 1 d . .
H1 H 0.6319 0.9179 0.4155 0.032 Uiso 1 1 d R U
N2 N 0.5504(5) 0.7028(7) 0.6454(5) 0.0370(14) Uani 1 1 d . .
H2 H 0.5287 0.6445 0.7069 0.044 Uiso 1 1 d R U
O3 O 0.8795(4) 0.1998(7) 0.8548(6) 0.0491(13) Uani 1 1 d . .
O4 O 0.7393(5) 0.3586(6) 0.9103(6) 0.0613(17) Uani 1 1 d . .
O5 O 0.7483(5) 0.2497(7) 0.7256(6) 0.0519(15) Uani 1 1 d . .
O2 O 0.7235(4) 0.0729(6) 0.8812(5) 0.0458(14) Uani 1 1 d . .
O6 O 0.8654(7) 0.8631(9) 0.7242(6) 0.083(3) Uani 1 1 d . .
O9 O 0.9042(5) 0.7884(7) 0.5425(5) 0.0516(15) Uani 1 1 d . .
O7 O 0.8694(7) 0.5840(8) 0.6713(7) 0.090(3) Uani 1 1 d . .
O8 O 1.0144(6) 0.7333(11) 0.6902(7) 0.085(3) Uani 1 1 d . .
O1 O 0.5648(5) 0.5547(6) 0.8570(5) 0.0549(15) Uani 1 1 d D .
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'
Cl Cl 0.1484 0.1585 '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'
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
N2 C1 C2 108.6(5)
N2 C1 H1A 110.0
C2 C1 H1A 110.0
N2 C1 H1B 110.0
C2 C1 H1B 110.0
H1A C1 H1B 108.4
N1 C2 C1 109.1(5)
N1 C2 H2A 109.9
C1 C2 H2A 109.9
N1 C2 H2B 109.9
C1 C2 H2B 109.9
H2A C2 H2B 108.3
N2 C3 C4 110.7(6)
N2 C3 H3A 109.5
C4 C3 H3A 109.5
N2 C3 H3B 109.5
C4 C3 H3B 109.5
H3A C3 H3B 108.1
C3 C4 N1 107.9(6)
C3 C4 H4A 110.1
N1 C4 H4A 110.1
C3 C4 H4B 110.1
N1 C4 H4B 110.1
H4A C4 H4B 108.4
N2 C5 C6 110.7(6)
N2 C5 H5A 109.5
C6 C5 H5A 109.5
N2 C5 H5B 109.5
C6 C5 H5B 109.5
H5A C5 H5B 108.1
N1 C6 C5 108.3(6)
N1 C6 H6A 110.0
C5 C6 H6A 110.0
N1 C6 H6B 110.0
C5 C6 H6B 110.0
H6A C6 H6B 108.4
O5 Cl1 O3 110.3(4)
O5 Cl1 O2 109.8(3)
O3 Cl1 O2 108.4(3)
O5 Cl1 O4 109.9(4)
O3 Cl1 O4 109.7(4)
O2 Cl1 O4 108.6(4)
O7 Cl2 O6 113.7(6)
O7 Cl2 O9 109.2(4)
O6 Cl2 O9 108.8(4)
O7 Cl2 O8 108.0(6)
O6 Cl2 O8 107.5(5)
O9 Cl2 O8 109.5(4)
C6 N1 C2 110.1(5)
C6 N1 C4 109.1(5)
C2 N1 C4 110.3(5)
C6 N1 H1 108.2
C2 N1 H1 109.3
C4 N1 H1 109.8
C5 N2 C3 110.1(7)
C5 N2 C1 108.1(6)
C3 N2 C1 110.6(7)
C5 N2 H2 110.4
C3 N2 H2 108.8
C1 N2 H2 108.8
H1WA O1 H1WB 110(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.496(8)
C1 C2 1.516(10)
C1 H1A 0.9700
C1 H1B 0.9700
C2 N1 1.495(8)
C2 H2A 0.9700
C2 H2B 0.9700
C3 N2 1.480(10)
C3 C4 1.493(10)
C3 H3A 0.9700
C3 H3B 0.9700
C4 N1 1.519(8)
C4 H4A 0.9700
C4 H4B 0.9700
C5 N2 1.476(10)
C5 C6 1.491(11)
C5 H5A 0.9700
C5 H5B 0.9700
C6 N1 1.486(8)
C6 H6A 0.9700
C6 H6B 0.9700
Cl1 O5 1.427(7)
Cl1 O3 1.436(5)
Cl1 O2 1.440(5)
Cl1 O4 1.443(6)
Cl2 O7 1.396(6)
Cl2 O6 1.396(6)
Cl2 O9 1.409(6)
Cl2 O8 1.427(8)
N1 H1 0.9100
N2 H2 0.9101
O1 H1WA 0.85(2)
O1 H1WB 0.84(2)
