#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/14/8101461.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_8101461
loop_
_publ_author_name
'Kolev, Tsonko'
'Glavcheva, Zornitza'
'Schürmann, Markus'
'Preut, Hans'
'Bleckmann, Paul'
'Radomirska, Valentina'
_publ_section_title
;
Crystal structure of bis[R-(+)-1-(1-naphthyl)ethylammonium]squarate, 
[C12H14N]2C4O4
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              187
_journal_page_last               188
_journal_volume                  214
_journal_year                    1999
_chemical_formula_structural     '[C12 H14 N]2 C4 O4'
_chemical_formula_sum            'C28 H28 N2 O4'
_chemical_formula_weight         456.52
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 109.26(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.373(2)
_cell_length_b                   7.367(2)
_cell_length_c                   14.100(3)
_cell_measurement_temperature    291(2)
_cell_volume                     1213.3(5)
_diffrn_ambient_temperature      291(2)
_exptl_crystal_density_diffrn    1.250
_refine_ls_R_factor_obs          0.0386
_refine_ls_wR_factor_obs         0.1055
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               8101461
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.07183(10) -0.30638(13) 0.22360(8) 0.0431(2) Uani 1 d . . .
O2 O -0.01418(12) -0.14108(16) 0.39492(8) 0.0532(3) Uani 1 d . . .
O3 O -0.03085(10) 0.25941(14) 0.29486(8) 0.0465(3) Uani 1 d . . .
O4 O 0.03796(10) 0.09060(14) 0.11305(8) 0.0438(2) Uani 1 d . . .
C41 C 0.04060(12) -0.15205(18) 0.23980(9) 0.0333(3) Uani 1 d . . .
C42 C 0.00327(12) -0.07499(18) 0.31943(10) 0.0357(3) Uani 1 d . . .
C43 C -0.00566(12) 0.10434(18) 0.27372(10) 0.0341(3) Uani 1 d . . .
C44 C 0.02697(11) 0.02674(17) 0.19181(9) 0.0335(3) Uani 1 d . . .
N11 N 0.06619(10) 0.50524(15) 0.44510(9) 0.0379(2) Uani 1 d . . .
H11A H 0.0405 0.4233 0.3964 0.057 Uiso 1 calc R . .
H11B H 0.0301 0.6102 0.4254 0.057 Uiso 1 calc R . .
H11C H 0.0530 0.4665 0.5001 0.057 Uiso 1 calc R . .
N31 N -0.03653(9) 0.45239(14) 0.07450(8) 0.0340(2) Uani 1 d . . .
H31A H -0.0067 0.3418 0.0888 0.051 Uiso 1 calc R . .
H31B H 0.0073 0.5319 0.1178 0.051 Uiso 1 calc R . .
H31C H -0.0402 0.4825 0.0124 0.051 Uiso 1 calc R . .
C1 C 0.25806(14) 0.3593(2) 0.50841(12) 0.0481(3) Uani 1 d . . .
C2 C 0.2844(2) 0.3169(3) 0.60821(14) 0.0642(5) Uani 1 d . . .
H2 H 0.2538 0.3869 0.6480 0.096 Uiso 1 calc R . .
C3 C 0.3561(2) 0.1710(3) 0.65162(16) 0.0777(7) Uani 1 d . . .
H3 H 0.3719 0.1447 0.7194 0.117 Uiso 1 calc R . .
C4 C 0.40234(19) 0.0681(3) 0.59541(19) 0.0740(6) Uani 1 d . . .
H4 H 0.4529 -0.0248 0.6256 0.111 Uiso 1 calc R . .
C5 C 0.4193(2) -0.0089(3) 0.4307(3) 0.0889(8) Uani 1 d . . .
H5 H 0.4690 -0.1035 0.4596 0.133 Uiso 1 calc R . .
C6 C 0.3901(3) 0.0231(5) 0.3304(3) 0.1051(10) Uani 1 d . . .
H6 H 0.4199 -0.0501 0.2912 0.158 Uiso 1 calc R . .
C7 C 0.3163(3) 0.1640(5) 0.2859(2) 0.0900(8) Uani 1 d . . .
H7 H 0.2964 0.1833 0.2171 0.135 Uiso 1 calc R . .
C8 C 0.27291(17) 0.2739(3) 0.34173(14) 0.0638(5) Uani 1 d . . .
H8 H 0.2244 0.3686 0.3107 0.096 Uiso 1 calc R . .
C9 C 0.30046(13) 0.2464(2) 0.44701(13) 0.0486(4) Uani 1 d . . .
C10 C 0.37461(15) 0.1002(3) 0.49168(17) 0.0605(5) Uani 1 d . . .
C11 C 0.19125(15) 0.5314(2) 0.46751(14) 0.0514(4) Uani 1 d . . .
H11 H 0.2045 0.5635 0.4048 0.077 Uiso 1 calc R . .
C12 C 0.2289(2) 0.6912(3) 0.5398(2) 0.0943(9) Uani 1 d . . .
H12A H 0.1970 0.8015 0.5057 0.141 Uiso 1 calc R . .
H12B H 0.3109 0.6994 0.5632 0.141 Uiso 1 calc R . .
H12C H 0.2025 0.6734 0.5960 0.141 Uiso 1 calc R . .
C21 C -0.22578(12) 0.30160(18) 0.02067(10) 0.0364(3) Uani 1 d . . .
C22 C -0.22282(14) 0.2662(2) -0.07360(12) 0.0478(3) Uani 1 d . . .
H22 H -0.1749 0.3349 -0.0983 0.072 Uiso 1 calc R . .
C23 C -0.28989(16) 0.1293(3) -0.13415(14) 0.0558(4) Uani 1 d . . .
H23 H -0.2848 0.1062 -0.1974 0.084 Uiso 1 calc R . .
C24 C -0.36234(14) 0.0306(2) -0.10009(14) 0.0531(4) Uani 1 d . . .
H24 H -0.4071 -0.0595 -0.1406 0.080 Uiso 1 calc R . .
C25 C -0.44769(14) -0.0363(3) 0.02994(16) 0.0594(5) Uani 1 d . . .
H25 H -0.4919 -0.1270 -0.0105 0.089 Uiso 1 calc R . .
C26 C -0.45883(16) -0.0024(3) 0.12028(17) 0.0671(5) Uani 1 d . . .
H26 H -0.5109 -0.0683 0.1413 0.101 Uiso 1 calc R . .
C27 C -0.39169(16) 0.1325(3) 0.18236(15) 0.0626(5) Uani 1 d . . .
H27 H -0.4001 0.1562 0.2443 0.094 Uiso 1 calc R . .
C28 C -0.31380(14) 0.2299(3) 0.15313(12) 0.0494(4) Uani 1 d . . .
H28 H -0.2688 0.3170 0.1960 0.074 Uiso 1 calc R . .
C29 C -0.30110(12) 0.1992(2) 0.05800(11) 0.0384(3) Uani 1 d . . .
C30 C -0.37051(13) 0.0628(2) -0.00431(13) 0.0448(3) Uani 1 d . . .
C31 C -0.15433(12) 0.45415(18) 0.08207(10) 0.0363(3) Uani 1 d . . .
H31 H -0.1475 0.4349 0.1526 0.054 Uiso 1 calc R . .
C32 C -0.20820(16) 0.6391(2) 0.05033(16) 0.0595(5) Uani 1 d . . .
H32A H -0.1619 0.7308 0.0932 0.089 Uiso 1 calc R . .
H32B H -0.2835 0.6410 0.0557 0.089 Uiso 1 calc R . .
H32C H -0.2133 0.6624 -0.0180 0.089 Uiso 1 calc R . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C41 1.2460(16) . ?
O2 C42 1.2523(17) . ?
O3 C43 1.2459(17) . ?
O4 C44 1.2541(16) . ?
C41 C42 1.4623(18) . ?
C41 C44 1.4649(18) . ?
C42 C43 1.4580(19) . ?
C43 C44 1.4599(17) . ?
N11 C11 1.486(2) . ?
N11 H11A 0.8900 . ?
N11 H11B 0.8900 . ?
N11 H11C 0.8900 . ?
N31 C31 1.4961(17) . ?
N31 H31A 0.8900 . ?
N31 H31B 0.8900 . ?
N31 H31C 0.8900 . ?
C1 C2 1.372(2) . ?
C1 C9 1.420(2) . ?
C1 C11 1.520(2) . ?
C2 C3 1.400(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.353(4) . ?
C3 H3 0.9300 . ?
C4 C10 1.408(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.361(5) . ?
C5 C10 1.415(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.388(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.358(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.424(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.420(3) . ?
C11 C12 1.526(3) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C21 C22 1.367(2) . ?
C21 C29 1.4277(19) . ?
C21 C31 1.5129(18) . ?
C22 C23 1.403(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.359(3) . ?
C23 H23 0.9300 . ?
C24 C30 1.407(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.349(3) . ?
C25 C30 1.408(2) . ?
C25 H25 0.9300 . ?
C26 C27 1.401(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.370(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.419(2) . ?
C28 H28 0.9300 . ?
C29 C30 1.422(2) . ?
C31 C32 1.518(2) . ?
C31 H31 0.9800 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653851
