#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/41/2234194.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_2234194
loop_
_publ_author_name
'Nowakowska, Monika'
'Gamble, Caryn'
'Levendis, Demetrius C.'
_publ_section_title
;
 Bis(adamantan-1-aminium) carbonate
;
_journal_coeditor_code           GK2467
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1159
_journal_paper_doi               10.1107/S1600536812011828
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '2C10 H18 N +, C O3 2-'
_chemical_formula_moiety         '2(C10 H18 N +), C O3 2-'
_chemical_formula_sum            'C21 H36 N2 O3'
_chemical_formula_weight         364.52
_chemical_name_systematic        'Bis(adamantan-1-aminium) carbonate'
_space_group_IT_number           165
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-P 3 2"c'
_symmetry_space_group_name_H-M   'P -3 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            2
_cell_length_a                   6.4340(6)
_cell_length_b                   6.4340(6)
_cell_length_c                   25.474(2)
_cell_measurement_reflns_used    819
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.78
_cell_measurement_theta_min      3.2
_cell_volume                     913.25(14)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker 2005)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997), Mercury (Macrae et al.,
2008) and
PLATON (Spek, 2009)
;
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            3187
_diffrn_reflns_theta_full        26.35
_diffrn_reflns_theta_max         26.35
_diffrn_reflns_theta_min         1.6
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     45
_refine_ls_number_reflns         629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.042
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0587P)²+0.0100P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1072
_reflns_number_gt                493
_reflns_number_total             629
_reflns_threshold_expression     I>2sigma(I)
_iucr_refine_instructions_details
;
TITL 10m_nikki1_0s in P-3c1
CELL  0.71069   6.4340   6.4340  25.4740   90.000   90.000  120.000
ZERR     2.00   0.0006   0.0006   0.0022    0.000    0.000    0.000
LATT   1
SYMM  - Y,   X - Y,   Z
SYMM  - X + Y, - X,   Z
SYMM    X - Y, - Y, 1/2 - Z
SYMM  - X, - X + Y, 1/2 - Z
SYMM    Y,   X, 1/2 - Z
SFAC  C    H    N    O
UNIT  42   72   4    6
MERG   2
OMIT    -2.00  56.00
HTAB
EQIV $1 -y+1, x-y+1, z
HTAB N1 O1_$1
FMAP   2
PLAN    5
SIZE     0.08   0.22   0.30
ACTA
BOND   $H
CONF
L.S.   8
TEMP  -100.00
WGHT    0.058700    0.010000
FVAR       0.39448
C1    1    0.666667    0.333333    0.164857    10.33333    0.01982    0.01982 =
         0.03123    0.00000    0.00000    0.00991
C2    1    0.921255    0.503438    0.145178    11.00000    0.01954    0.02051 =
         0.04150   -0.00143   -0.00178    0.00872
AFIX  23
H2A   2    1.031976    0.450495    0.158427    11.00000   -1.20000
H2B   2    0.976952    0.667787    0.158343    11.00000   -1.20000
AFIX   0
C3    1    0.921541    0.503303    0.084978    11.00000    0.02166    0.02616 =
         0.04038    0.00391    0.00613    0.00852
AFIX  13
H3    2    1.087705    0.614025    0.071890    11.00000   -1.20000
AFIX   0
C4    1    0.836463    0.248208    0.065020    11.00000    0.03171    0.03498 =
         0.03968   -0.00164    0.00550    0.01848
AFIX  23
H4A   2    0.838011    0.247367    0.026161    11.00000   -1.20000
H4B   2    0.946430    0.193209    0.077675    11.00000   -1.20000
AFIX   0
C5    1    0.000000    0.000000    0.250000    10.16667    0.02140    0.02140 =
         0.02283    0.00000    0.00000    0.01070
N1    3    0.666667    0.333333    0.223725    10.33333    0.02535    0.02535 =
         0.03278    0.00000    0.00000    0.01267
O1    4    0.000000    0.199256    0.250000    10.50000    0.02990    0.02213 =
         0.05358   -0.00455   -0.00910    0.01495
H1    2    0.732054    0.502447    0.235771    11.00000    0.05963
HKLF    4
REM  10m_nikki1_0s in P-3c1
REM R1 =  0.0420 for    493 Fo > 4sig(Fo)  and  0.0543 for all    629 data
REM     45 parameters refined using      0 restraints
END
WGHT      0.0587      0.0100
REM Highest difference peak  0.223,  deepest hole -0.181,  1-sigma level  0.046
Q1    1   0.7950  0.4169  0.1578  11.00000  0.05    0.22
Q2    1   0.9170  0.1470  0.0459  11.00000  0.05    0.16
Q3    1   1.1879  0.7050  0.1802  11.00000  0.05    0.13
Q4    1   1.1289  0.6049  0.1695  11.00000  0.05    0.13
Q5    1   0.8631  0.3776  0.0767  11.00000  0.05    0.13
;
_cod_data_source_file            gk2467.cif
_cod_data_source_block           I
_cod_database_code               2234194
_cod_database_fobs_code          2234194
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'y, x, -z+1/2'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-y, -x, z-1/2'
loop_
_atom_site_type_symbol
_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_symmetry_multiplicity
C C1 0.6667 0.3333 0.16486(9) 0.0236(6) Uani d S 1 3
C C2 0.9213(2) 0.5034(2) 0.14518(6) 0.0278(4) Uani d . 1 1
H H2A 1.032 0.4505 0.1584 0.033 Uiso calc R 1 1
H H2B 0.977 0.6678 0.1583 0.033 Uiso calc R 1 1
C C3 0.9215(2) 0.5033(3) 0.08498(6) 0.0309(4) Uani d . 1 1
H H3 1.0877 0.614 0.0719 0.037 Uiso calc R 1 1
C C4 0.8365(3) 0.2482(3) 0.06502(6) 0.0346(4) Uani d . 1 1
H H4A 0.838 0.2474 0.0262 0.042 Uiso calc R 1 1
H H4B 0.9464 0.1932 0.0777 0.042 Uiso calc R 1 1
C C5 0 0 0.25 0.0219(7) Uani d S 1 6
N N1 0.6667 0.3333 0.22372(8) 0.0278(5) Uani d S 1 3
O O1 0 0.1993(2) 0.25 0.0343(4) Uani d S 1 2
H H1 0.732(4) 0.502(3) 0.2358(7) 0.060(5) Uiso d . 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0198(8) 0.0198(8) 0.0312(12) 0.0099(4) 0 0
C2 0.0195(8) 0.0205(7) 0.0415(9) 0.0087(6) -0.0018(6) -0.0014(6)
C3 0.0217(8) 0.0262(8) 0.0404(9) 0.0085(6) 0.0061(6) 0.0039(6)
C4 0.0317(9) 0.0350(9) 0.0397(8) 0.0185(8) 0.0055(6) -0.0016(7)
C5 0.0214(10) 0.0214(10) 0.0228(15) 0.0107(5) 0 0
N1 0.0253(7) 0.0253(7) 0.0328(11) 0.0127(3) 0 0
O1 0.0299(8) 0.0221(6) 0.0536(10) 0.0149(4) -0.0091(7) -0.0045(3)
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 0 '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 0.006 '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_site_symmetry_1
_geom_angle
N1 C1 C2 . 109.13(9)
C2 C1 C2 3_665 109.81(9)
C1 C2 C3 . 109.18(12)
C1 C2 H2A . 109.8
C3 C2 H2A . 109.8
C1 C2 H2B . 109.8
C3 C2 H2B . 109.8
H2A C2 H2B . 108.3
C4 C3 C2 2_655 109.29(11)
C4 C3 C4 2_655 109.58(14)
C2 C3 C4 . 109.40(12)
C2 C3 H3 . 109.5
C4 C3 H3 . 109.5
C3 C4 C3 3_665 109.57(13)
C3 C4 H4A . 109.8
C3 C4 H4B . 109.8
H4A C4 H4B . 108.2
O1 C5 O1 2 120
C1 N1 H1 . 107.9(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.500(3)
C1 C2 . 1.5295(14)
C2 C3 . 1.5335(19)
C2 H2A . 0.99
C2 H2B . 0.99
C3 C4 2_655 1.532(2)
C3 C4 . 1.534(2)
C3 H3 . 1
C4 H4A . 0.99
C4 H4B . 0.99
C5 O1 . 1.2820(13)
N1 H1 . 0.999(16)
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
N1 H1 O1 2_665 0.999(16) 1.778(15) 2.7644(11) 168.7(18)
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
N1 C1 C2 C3 . . 179.92(8)
C2 C1 C2 C3 3_665 . 60.34(13)
C2 C1 C2 C3 2_655 . -60.50(13)
C1 C2 C3 C4 . 2_655 60.13(13)
C1 C2 C3 C4 . . -59.84(12)
C4 C3 C4 C3 2_655 3_665 -59.76(18)
C2 C3 C4 C3 . 3_665 60.04(15)
