#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/23/2012383.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_2012383
loop_
_publ_author_name
'Chebbi, Hammouda'
'Driss, Ahmed'
_publ_section_title
;
 4-Ammonio-2,2,6,6-tétraméthylpipéridinium chromate dihydrate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1369
_journal_page_last               1370
_journal_paper_doi               10.1107/S0108270101008447
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C9 H22 N2 2+ , Cr O4 2- , 2H2 O'
_chemical_formula_moiety         'C9 H22 N2 2+ , Cr O4 2- , 2H2 O'
_chemical_formula_sum            'C9 H26 Cr N2 O6'
_chemical_formula_weight         310.32
_chemical_name_systematic
;
4-ammonio-2,2,6,6-tétraméthylpipéridinium chromate dihydrate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 101.73(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.566(9)
_cell_length_b                   9.617(2)
_cell_length_c                   22.025(11)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27
_cell_measurement_theta_min      2.62
_cell_volume                     2813(2)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection
'CAD-4 EXPRESS (Duisenberg, 1992; Macíček & Yordanov, 1992)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1997) et PLATON (Spek, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .499
_diffrn_measured_fraction_theta_max .499
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_av_R_equivalents  .017
_diffrn_reflns_av_sigmaI/netI    .035
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            3194
_diffrn_reflns_theta_full        26.98
_diffrn_reflns_theta_max         26.98
_diffrn_reflns_theta_min         2.61
_diffrn_standards_decay_%        .6
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    .834
_exptl_absorpt_correction_T_max  .812
_exptl_absorpt_correction_T_min  .804
_exptl_absorpt_correction_type   \y-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          .58
_exptl_crystal_size_mid          .29
_exptl_crystal_size_min          .25
_refine_diff_density_max         .54
_refine_diff_density_min         -.57
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          .064
_refine_ls_R_factor_gt           .044
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0698P)²+3.9256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .119
_refine_ls_wR_factor_ref         .132
_reflns_number_gt                2388
_reflns_number_total             3066
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ln1120.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2012383
_cod_database_fobs_code          2012383
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y, -z-1/2'
'-x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z-1/2'
loop_
_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cr .31062(3) .54178(4) .122497(19) .02853(16) Uani d . 1 . . Cr
O1 .3168(2) .6051(3) .05463(10) .0557(7) Uani d . 1 . . O
O2 .4179(3) .4720(4) .15596(16) .1002(14) Uani d . 1 . . O
O3 .2199(3) .4295(3) .11497(13) .0779(10) Uani d . 1 . . O
O4 .2910(2) .6721(3) .16653(13) .0545(7) Uani d . 1 . . O
N1 .25733(16) .9187(2) .07077(10) .0224(4) Uani d . 1 . . N
N2 .3267(2) 1.1256(3) .24467(12) .0357(6) Uani d . 1 . . N
C1 .1156(2) 1.0927(3) .06007(14) .0367(7) Uani d . 1 . . C
H11 .1107 1.0768 .0165 .050 Uiso calc R 1 . . H
H12 .1546 1.1750 .0723 .050 Uiso calc R 1 . . H
H13 .0493 1.1045 .0684 .050 Uiso calc R 1 . . H
C2 .35561(18) 1.0008(3) .08380(11) .0234(5) Uani d . 1 . . C
C3 .38135(18) 1.0330(3) .15337(11) .0262(5) Uani d . 1 . . C
H31 .4002 .9474 .1760 .050 Uiso calc R 1 . . H
H32 .4389 1.0950 .1618 .050 Uiso calc R 1 . . H
C4 .29413(19) 1.0997(3) .17662(11) .0266(5) Uani d . 1 . . C
H4 .2758 1.1879 .1549 .050 Uiso calc R 1 . . H
C5 .2036(2) 1.0020(3) .16538(12) .0274(5) Uani d . 1 . . C
H51 .1491 1.0448 .1811 .050 Uiso calc R 1 . . H
H52 .2217 .9164 .1882 .050 Uiso calc R 1 . . H
C6 .16692(18) .9676(3) .09681(12) .0240(5) Uani d . 1 . . C
C7 .0937(2) .8452(3) .08804(14) .0331(6) Uani d . 1 . . C
H71 .0352 .8691 .1041 .050 Uiso calc R 1 . . H
H72 .1259 .7656 .1098 .050 Uiso calc R 1 . . H
H73 .0739 .8239 .0447 .050 Uiso calc R 1 . . H
C8 .4350(2) .9062(3) .06596(15) .0369(7) Uani d . 1 . . C
H81 .4995 .9511 .0758 .050 Uiso calc R 1 . . H
H82 .4181 .8875 .0223 .050 Uiso calc R 1 . . H
H83 .4376 .8204 .0885 .050 Uiso calc R 1 . . H
C9 .3464(2) 1.1318(3) .04422(13) .0349(6) Uani d . 1 . . C
H91 .4121 1.1706 .0458 .050 Uiso calc R 1 . . H
H92 .3050 1.1984 .0598 .050 Uiso calc R 1 . . H
H93 .3164 1.1089 .0021 .050 Uiso calc R 1 . . H
O5 .5000 .3046(4) .2500 .0405(8) Uani d S 1 . . O
O6 .5000 .6913(5) .2500 .0648(12) Uani d S 1 . . O
O7 .1342(3) .3619(4) .20900(16) .0817(11) Uani d . 1 . . O
H1N1 .270(2) .839(3) .0830(12) .015(6) Uiso d . 1 . . H
H2N1 .241(3) .916(4) .0297(18) .048(10) Uiso d . 1 . . H
H1N2 .370(3) 1.184(4) .2506(16) .038(9) Uiso d . 1 . . H
H2N2 .280(3) 1.158(5) .2639(19) .066(13) Uiso d . 1 . . H
H3N2 .349(3) 1.047(5) .2596(19) .055(12) Uiso d . 1 . . H
HO5 .519(3) .346(4) .2744(17) .049(12) Uiso d . 1 . . H
HO6 .523(4) .642(5) .273(2) .086(18) Uiso d . 1 . . H
H1O7 .089(3) .323(5) .208(2) .053(14) Uiso d . 1 . . H
H2O7 .144(4) .377(5) .170(2) .085(16) Uiso d . 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cr Cr .3209 .6236 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-4 4 -5
-6 -4 -6
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O3 Cr O1 109.53(14) n
O3 Cr O2 111.1(2) n
O1 Cr O2 111.07(16) n
O3 Cr O4 111.03(15) n
O1 Cr O4 107.53(14) n
O2 Cr O4 106.50(18) n
C2 N1 C6 120.46(19) y
C2 N1 H1N1 107.5(19) n
C6 N1 H1N1 107.4(18) n
C2 N1 H2N1 104(2) n
C6 N1 H2N1 110(2) n
H1N1 N1 H2N1 107(3) n
C4 N2 H1N2 110(2) n
C4 N2 H2N2 116(3) n
H1N2 N2 H2N2 104(4) n
C4 N2 H3N2 104(3) n
H1N2 N2 H3N2 111(4) n
H2N2 N2 H3N2 111(4) n
C6 C1 H11 109.5 n
C6 C1 H12 109.5 n
H11 C1 H12 109.5 n
C6 C1 H13 109.5 n
H11 C1 H13 109.5 n
H12 C1 H13 109.5 n
C8 C2 C9 109.1(2) n
C8 C2 N1 106.2(2) y
C9 C2 N1 110.7(2) y
C8 C2 C3 110.5(2) y
C9 C2 C3 112.4(2) n
N1 C2 C3 107.8(2) y
C4 C3 C2 112.7(2) y
C4 C3 H31 109.0 n
C2 C3 H31 109.0 n
C4 C3 H32 109.0 n
C2 C3 H32 109.0 n
H31 C3 H32 107.8 n
N2 C4 C3 108.4(2) y
N2 C4 C5 109.2(2) y
C3 C4 C5 109.9(2) n
N2 C4 H4 109.8 n
C3 C4 H4 109.8 n
C5 C4 H4 109.8 n
C4 C5 C6 112.5(2) y
C4 C5 H51 109.1 n
C6 C5 H51 109.1 n
C4 C5 H52 109.1 n
C6 C5 H52 109.1 n
H51 C5 H52 107.8 n
C7 C6 C5 111.4(2) y
C7 C6 N1 105.4(2) n
C5 C6 N1 108.2(2) y
C7 C6 C1 108.9(2) n
C5 C6 C1 111.9(2) n
N1 C6 C1 110.8(2) y
C6 C7 H71 109.5 n
C6 C7 H72 109.5 n
H71 C7 H72 109.5 n
C6 C7 H73 109.5 n
H71 C7 H73 109.5 n
H72 C7 H73 109.5 n
C2 C8 H81 109.5 n
C2 C8 H82 109.5 n
H81 C8 H82 109.5 n
C2 C8 H83 109.5 n
H81 C8 H83 109.5 n
H82 C8 H83 109.5 n
C2 C9 H91 109.5 n
C2 C9 H92 109.5 n
H91 C9 H92 109.5 n
C2 C9 H93 109.5 n
H91 C9 H93 109.5 n
H92 C9 H93 109.5 n
H1O7 O7 H2O7 110(5) n
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
Cr O3 . 1.620(3) n
Cr O1 . 1.632(2) n
Cr O2 . 1.635(3) n
Cr O4 . 1.640(2) n
N1 C2 . 1.526(3) y
N1 C6 . 1.530(3) y
N1 H1N1 . .82(3) n
N1 H2N1 . .89(4) n
N2 C4 . 1.495(3) y
N2 H1N2 . .80(4) n
N2 H2N2 . .89(5) n
N2 H3N2 . .86(4) n
C1 C6 . 1.536(4) y
C1 H11 . .9600 n
C1 H12 . .9600 n
C1 H13 . .9600 n
C2 C8 . 1.521(4) y
C2 C9 . 1.522(4) y
C2 C3 . 1.532(3) n
C3 C4 . 1.523(4) y
C3 H31 . .9700 n
C3 H32 . .9700 n
C4 C5 . 1.527(4) y
C4 H4 . .9800 n
C5 C6 . 1.527(4) y
C5 H51 . .9700 n
C5 H52 . .9700 n
C6 C7 . 1.527(3) y
C7 H71 . .9600 n
C7 H72 . .9600 n
C7 H73 . .9600 n
C8 H81 . .9600 n
C8 H82 . .9600 n
C8 H83 . .9600 n
C9 H91 . .9600 n
C9 H92 . .9600 n
C9 H93 . .9600 n
O5 HO5 . .68(3) n
O6 HO6 . .72(5) n
O7 H1O7 . .72(4) n
O7 H2O7 . .92(5) n
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
_geom_hbond_publ_flag
N1 H1N1 O1 . .82(3) 2.45(3) 3.161(4) 145(2) y
N1 H1N1 O4 . .82(3) 2.41(3) 3.144(4) 149(2) y
N1 H2N1 O1 7_565 .89(4) 1.87(4) 2.750(4) 169(4) y
N2 H1N2 O5 1_565 .80(4) 2.11(4) 2.897(4) 165(4) y
N2 H2N2 O4 8_556 .89(4) 1.97(4) 2.801(4) 154(4) y
N2 H3N2 O7 8_556 .85(5) 1.91(5) 2.745(5) 166(4) y
O5 HO5 O2 6_656 .68(4) 2.00(4) 2.680(5) 176(3) y
O6 HO6 O2 6_656 .72(5) 2.29(5) 3.007(5) 174(6) y
O7 H1O7 O6 3_445 .72(4) 2.09(4) 2.738(5) 151(5) y
O7 H2O7 O3 . .91(5) 1.81(5) 2.653(5) 153(5) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652333
