#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011381.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_2011381
loop_
_publ_author_name
'Paix\~ao, J. A.'
'Matos Beja, A.'
'Ramos Silva, M.'
'Martin-Gil, J.'
_publ_section_title
;
 Two anilinium salts: anilinium hydrogenphosphite and anilinium
 hydrogenoxalate hemihydrate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1132
_journal_page_last               1135
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C6 H8 N +, H2 P O3 -'
_chemical_formula_sum            'C6 H10 N O3 P'
_chemical_formula_weight         175.12
_chemical_name_systematic
;
  Anilinium hydrogenphosphite
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.91(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.216(2)
_cell_length_b                   14.219(6)
_cell_length_c                   9.342(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      15.21
_cell_measurement_theta_min      9.74
_cell_volume                     825.6(5)
_computing_cell_refinement       'CAD-4 software'
_computing_data_collection       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_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 .998
_diffrn_measured_fraction_theta_max .998
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4 diffractometer'
_diffrn_measurement_method       'profile data from \w-2\q scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .0227
_diffrn_reflns_av_sigmaI/netI    .0234
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3607
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         3.58
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  180
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .292
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          .34
_exptl_crystal_size_mid          .34
_exptl_crystal_size_min          .34
_refine_diff_density_max         .252
_refine_diff_density_min         -.252
_refine_ls_extinction_coef       .015(2)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          .0496
_refine_ls_R_factor_gt           .0283
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0380P)^2^+0.3216P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .0839
_reflns_number_gt                1221
_reflns_number_total             1612
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    sk1377.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  P21/a
_cod_database_code               2011381
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
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_occupancy
_atom_site_type_symbol
P1 .03258(8) .36864(3) .40048(5) .03614(17) Uani d 1 P
H1 -.022(3) .3043(14) .491(2) .048(6) Uiso d 1 H
O1 .1077(2) .32294(10) .26648(14) .0448(4) Uani d 1 O
O2 -.1538(2) .43441(10) .38316(16) .0503(4) Uani d 1 O
O3 .2302(2) .41784(12) .47158(17) .0564(5) Uani d 1 O
H8 .196(5) .464(2) .519(3) .085 Uiso d 1 H
C1 .0613(3) .12860(12) .04184(18) .0335(4) Uani d 1 C
C2 .2505(3) .09411(16) -.0102(2) .0466(5) Uani d 1 C
H2 .360(4) .0804(17) .054(3) .061(7) Uiso d 1 H
C3 .2716(4) .08397(19) -.1567(3) .0584(6) Uani d 1 C
H3 .401(4) .0613(18) -.190(3) .072(8) Uiso d 1 H
C4 .1064(4) .10847(18) -.2485(3) .0601(6) Uani d 1 C
H4 .121(4) .101(2) -.349(3) .074(8) Uiso d 1 H
C5 -.0816(4) .14348(19) -.1948(2) .0607(6) Uani d 1 C
H5 -.201(5) .162(2) -.260(3) .083(9) Uiso d 1 H
C6 -.1051(4) .15338(16) -.0487(2) .0482(5) Uani d 1 C
H6 -.234(4) .1749(18) -.012(3) .060(7) Uiso d 1 H
N .0369(3) .14186(13) .19561(17) .0369(4) Uani d 1 N
H7A .133(4) .1060(17) .253(3) .055(6) Uiso d 1 H
H7B -.097(4) .1337(17) .218(3) .057(7) Uiso d 1 H
H7C .071(4) .2033(19) .222(3) .060(7) Uiso d 1 H
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
P1 .0381(3) .0390(3) .0314(2) .0007(2) .00316(17) -.0048(2)
O1 .0461(8) .0472(8) .0411(8) -.0013(6) .0051(6) -.0141(6)
O2 .0365(7) .0567(9) .0575(9) .0059(6) -.0077(6) -.0239(7)
O3 .0450(9) .0612(10) .0624(10) .0150(7) -.0171(7) -.0274(8)
C1 .0377(9) .0282(8) .0347(9) -.0031(8) .0006(7) -.0051(7)
C2 .0418(11) .0513(12) .0465(11) .0052(10) -.0007(9) -.0069(9)
C3 .0546(14) .0668(16) .0543(13) .0054(12) .0150(11) -.0135(11)
C4 .0786(17) .0638(15) .0381(11) -.0033(13) .0048(11) -.0094(10)
C5 .0679(15) .0716(16) .0422(12) .0084(13) -.0133(11) -.0042(11)
C6 .0454(12) .0560(13) .0432(11) .0093(10) -.0039(9) -.0065(9)
N .0355(9) .0404(9) .0349(8) -.0003(7) -.0002(7) -.0034(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
P P .1023 .0942 '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'
O O .0106 .0060 '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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O1 P1 O2 115.70(8) yes
O1 P1 O3 107.40(9) yes
O2 P1 O3 111.75(9) yes
O1 P1 H1 109.0(9) ?
O2 P1 H1 107.7(9) ?
O3 P1 H1 104.6(9) ?
P1 O3 H8 112(2) ?
C2 C1 C6 121.09(18) ?
C2 C1 N 119.90(17) ?
C6 C1 N 118.99(17) ?
C1 C2 C3 118.9(2) ?
C1 C2 H2 118.2(15) ?
C3 C2 H2 122.9(15) ?
C4 C3 C2 120.6(2) ?
C4 C3 H3 121.5(17) ?
C2 C3 H3 117.9(17) ?
C3 C4 C5 119.8(2) ?
C3 C4 H4 120.4(16) ?
C5 C4 H4 119.8(16) ?
C4 C5 C6 120.1(2) ?
C4 C5 H5 120.7(17) ?
C6 C5 H5 119.2(17) ?
C1 C6 C5 119.5(2) ?
C1 C6 H6 120.0(15) ?
C5 C6 H6 120.5(15) ?
C1 N H7A 114.5(14) ?
C1 N H7B 109.7(16) ?
H7A N H7B 113(2) ?
C1 N H7C 110.7(15) ?
H7A N H7C 103(2) ?
H7B N H7C 106(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P1 O1 1.4919(14) yes
P1 O2 1.4954(15) yes
P1 O3 1.5538(16) yes
P1 H1 1.29(2) yes
O3 H8 .82(3) ?
C1 C2 1.370(3) ?
C1 C6 1.371(3) ?
C1 N 1.459(2) ?
C2 C3 1.385(3) ?
C2 H2 .92(2) ?
C3 C4 1.372(4) ?
C3 H3 .92(3) ?
C4 C5 1.373(4) ?
C4 H4 .95(3) ?
C5 C6 1.382(3) ?
C5 H5 .99(3) ?
C6 H6 .93(3) ?
N H7A .94(3) ?
N H7B .87(3) ?
N H7C .93(3) ?
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
O3 H8 O2 3_566 .82(3) 1.74(3) 2.550(2) 173(3)
N H7A O2 4_665 .94(3) 1.88(3) 2.799(2) 165(2)
N H7B O1 4_565 .87(3) 2.00(3) 2.804(2) 154(2)
N H7C O1 . .93(3) 1.77(3) 2.693(2) 174(2)
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_publ_flag
C6 C1 C2 C3 -.4(3) ?
N C1 C2 C3 -178.7(2) yes
C1 C2 C3 C4 .3(4) ?
C2 C3 C4 C5 .1(4) ?
C3 C4 C5 C6 -.5(4) ?
C2 C1 C6 C5 .0(3) ?
N C1 C6 C5 178.3(2) yes
C4 C5 C6 C1 .5(4) ?