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#$Date: 2023-03-24 10:59:29 +0100 (Fri 24 de Mar de 2023) $
#$Revision: 282041 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/69/8106979.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_8106979
loop_
_publ_author_name
'Socha, Paweƚ'
'Dobrzycki, Lukasz'
_publ_section_title
;
 Crystal structure of 4,4′-bipiperidinium dichloride 0.12 hydrate,
 C10H22N2Cl2 · 0.12 H2O
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              693
_journal_page_last               694
_journal_paper_doi               10.1515/ncrs-2015-0234
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C10 H22.24 Cl2 N2 O0.12'
_chemical_formula_weight         243.36
_chemical_name_systematic
; 
4,4'bipiperidinium dichloride 0.12 hydrate
;
_space_group_IT_number           64
_space_group_name_Hall           '-C 2ac 2'
_space_group_name_H-M_alt        'C m c e'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'C m c e'
_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                   9.6661(8)
_cell_length_b                   7.3063(6)
_cell_length_c                   19.3270(15)
_cell_measurement_reflns_used    2133
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.103
_cell_measurement_theta_min      2.108
_cell_volume                     1364.94(19)
_computing_cell_refinement       'SAINT [2]'
_computing_data_collection       'APEX2 [2]'
_computing_data_reduction        'SAINT [2]'
_computing_molecular_graphics    'Diamond 3.2 [4]'
_computing_publication_material  'SHELXL-97 [3]'
_computing_structure_refinement  'SHELXL-97 [3]'
_computing_structure_solution    'SHELXS-97 [3]'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEX II CCD'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  'Triumph monochromator'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7177
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.448
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Bruker AXS, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             525
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     44
_refine_ls_number_reflns         1054
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0359
_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)+(0.0570P)²+0.4792P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                881
_reflns_number_total             1054
_reflns_threshold_expression     >2sigma(I)
_iucr_refine_instructions_details
;
TITL 1 in Cmca
CELL  0.71073   9.6661   7.3063  19.3270   90.000   90.000   90.000
ZERR     4.00   0.0008   0.0006   0.0015    0.000    0.000    0.000
LATT   7
SYMM  1/2-X, -Y, 1/2+Z
SYMM  X, -Y, -Z
SYMM  1/2-X,   Y, 1/2-Z
SFAC  C    H    N    O    Cl
UNIT  40   88.96   8    0.48    8
MERG   4
LIST 4
FMAP   2
omit -2 60
PLAN   7
BOND $h
eqiv $1 x+1/2, y, -z+1/2
eqiv $2 x+1/2, y+1/2, z
eqiv $3 x, 1-y, 1-z
htab
htab N1 Cl1_$1
htab N1 Cl1_$2
htab O1 Cl1
 
rtab d1 cl1 o1 cl1_$3
 
conf
acta 60
SIZE 0.124 0.164 0.193
L.S.   4
TEMP   -100
 
WGHT    0.057000    0.479200
FVAR       0.12872   0.02980
mole 1
CL1   5    0.000000    0.547060    0.339469    10.50000    0.03798    0.02367 =
         0.04478   -0.00105    0.00000    0.00000
mole 2
N1    3    0.500000    0.625225    0.318094    10.50000    0.03870    0.02369 =
         0.04335   -0.00261    0.00000    0.00000
H1N   2    0.500000    0.607312    0.273169    10.50000   -1.50000
H2N   2    0.500000    0.743824    0.324223    10.50000   -1.50000
C2    1    0.372370    0.545037    0.348652    11.00000    0.02922    0.03438 =
         0.04937   -0.00232   -0.00412   -0.00049
AFIX  23
H2A   2    0.367579    0.413074    0.337274    11.00000   -1.20000
H2B   2    0.290079    0.605601    0.328508    11.00000   -1.20000
AFIX   0
C3    1    0.371540    0.569213    0.426380    11.00000    0.02421    0.03582 =
         0.04789    0.00036   -0.00099    0.00147
AFIX  23
H3A   2    0.287768    0.510288    0.445674    11.00000   -1.20000
H3B   2    0.366951    0.701405    0.437391    11.00000   -1.20000
AFIX   0
C4    1    0.500000    0.486496    0.460799    10.50000    0.02450    0.02048 =
         0.04629   -0.00090    0.00000    0.00000
AFIX  13
H4    2    0.500000    0.351936    0.451339    10.50000   -1.20000
AFIX   0
mole 3
O1    4    0.047814    0.500000    0.500000    21.00000    0.04668
AFIX   3
H1X   2   -0.041070    0.493900    0.520150    21.00000   -1.50000
H2X   2    0.034110    0.514170    0.451670    21.00000   -1.50000
HKLF    4
 
REM  1 in Cmca
REM R1 =  0.0359 for    881 Fo > 4sig(Fo)  and  0.0448 for all   1054 data
REM     44 parameters refined using      0 restraints
 
END  
     
WGHT      0.0570      0.4792 
REM Highest difference peak  0.355,  deepest hole -0.288,  1-sigma level  0.053
Q1    1   0.5610  0.5297  0.4446  11.00000  0.05    0.36
Q2    1   0.3827  0.5523  0.3875  11.00000  0.05    0.32
Q3    1   0.5000  0.5000  0.5000  10.25000  0.05    0.31
Q4    1  -0.0812  0.5392  0.3370  11.00000  0.05    0.30
Q5    1  -0.0453  0.5537  0.3020  11.00000  0.05    0.29
Q6    1   0.4375  0.5754  0.3373  11.00000  0.05    0.27
Q7    1   0.0000  0.4598  0.3194  10.50000  0.05    0.24


;
_cod_data_source_file            suppl_ncrs-2015-0234_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      Cmca
_cod_database_code               8106979
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x, -y, -z'
'-x+1/2, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x, y, z'
'x-1/2, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x, y+1/2, -z-1/2'
'-x+1/2, y+1/2, z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.0000 0.54706(6) 0.33947(2) 0.03548(17) Uani 1 2 d S . .
N1 N 0.5000 0.6252(2) 0.31809(10) 0.0352(4) Uani 1 2 d S . .
H1N H 0.5000 0.607(4) 0.2732(16) 0.053 Uiso 1 2 d S . .
H2N H 0.5000 0.744(5) 0.3242(13) 0.053 Uiso 1 2 d S . .
C2 C 0.37237(15) 0.54504(18) 0.34865(7) 0.0377(3) Uani 1 1 d . . .
H2A H 0.3676 0.4131 0.3373 0.045 Uiso 1 1 calc R . .
H2B H 0.2901 0.6056 0.3285 0.045 Uiso 1 1 calc R . .
C3 C 0.37154(13) 0.56921(18) 0.42638(7) 0.0360(3) Uani 1 1 d . . .
H3A H 0.2878 0.5103 0.4457 0.043 Uiso 1 1 calc R . .
H3B H 0.3670 0.7014 0.4374 0.043 Uiso 1 1 calc R . .
C4 C 0.5000 0.4865(2) 0.46080(10) 0.0304(4) Uani 1 2 d S . .
H4 H 0.5000 0.3519 0.4513 0.037 Uiso 1 2 calc SR . .
O1 O 0.048(3) 0.5000 0.5000 0.047(8) Uiso 0.060(5) 2 d SP . .
H1X H -0.0411 0.4939 0.5202 0.070 Uiso 0.030(2) 1 d PR . .
H2X H 0.0341 0.5142 0.4517 0.070 Uiso 0.030(2) 1 d PR . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0380(3) 0.0237(2) 0.0448(3) -0.00105(16) 0.000 0.000
N1 0.0387(9) 0.0237(7) 0.0434(9) -0.0026(6) 0.000 0.000
C2 0.0292(7) 0.0344(7) 0.0494(8) -0.0023(6) -0.0041(5) -0.0005(5)
C3 0.0242(6) 0.0358(6) 0.0479(8) 0.0004(5) -0.0010(5) 0.0015(5)
C4 0.0245(8) 0.0205(7) 0.0463(10) -0.0009(7) 0.000 0.000
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.0000 '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
C2 N1 C2 112.01(16) . 11_655
C2 N1 H1N 109.5(9) . .
C2 N1 H2N 109.7(8) . .
H1N N1 H2N 106(2) . .
N1 C2 C3 110.65(12) . .
N1 C2 H2A 109.5 . .
C3 C2 H2A 109.5 . .
N1 C2 H2B 109.5 . .
C3 C2 H2B 109.5 . .
H2A C2 H2B 108.1 . .
C2 C3 C4 112.37(12) . .
C2 C3 H3A 109.1 . .
C4 C3 H3A 109.1 . .
C2 C3 H3B 109.1 . .
C4 C3 H3B 109.1 . .
H3A C3 H3B 107.9 . .
C4 C4 C3 112.30(11) 9_666 .
C3 C4 C3 108.21(15) 11_655 .
C3 C4 H4 108.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C2 1.4880(17) .
N1 H1N 0.88(3) .
N1 H2N 0.87(3) .
C2 C3 1.513(2) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.5328(17) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C4 1.528(4) 9_666
C4 H4 1.0000 .
O1 H1X 0.9444 .
O1 H2X 0.9491 .
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
N1 H1N Cl1 0.88(3) 2.22(3) 3.0983(19) 177(2) 10_656
N1 H2N Cl1 0.87(3) 2.24(3) 3.1096(17) 180(2) 5
O1 H2X Cl1 0.95 2.21 3.156(4) 179.4 .
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C2 N1 C2 C3 56.73(19) 11_655 . . .
N1 C2 C3 C4 -56.44(15) . . . .
C2 C3 C4 C4 179.17(15) . . . 9_666
C2 C3 C4 C3 54.65(18) . . . 11_655
