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#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/18/8101835.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_8101835
loop_
_publ_author_name
'M. Ramos Silva'
'J. A. Paixão'
'A. Matos Beja'
_publ_section_title
;
Crystal structure of L-tryptophanium phosphite, (C₁₁H₁₃N₂O₂)
[H₂PO₃]
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              487
_journal_page_last               488
_journal_volume                  220
_journal_year                    2005
_chemical_absolute_configuration rm
_chemical_formula_moiety         ' C11H13N2O2^+^, H2PO3^-^ '
_chemical_formula_sum            'C11 H15 N2 O5 P'
_chemical_formula_weight         286.22
_chemical_name_systematic
; 
 L-tryptophanium phosphite
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                   5.5442(6)
_cell_length_b                   8.3603(4)
_cell_length_c                   27.427(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      16.95
_cell_measurement_theta_min      4.94
_cell_volume                     1271.3(2)
_computing_cell_refinement       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_reduction        'HELENA (Spek, 2003)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       'omega/2theta, profile data'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_sigmaI/netI    0.0941
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            3366
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.30
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  180
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'North et al. (1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.45(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1343
_refine_ls_R_factor_gt           0.0529
_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)+(0.0824P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1462
_reflns_number_gt                1801
_reflns_number_total             2892
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1609.cff
_cod_data_source_block           triptp
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               8101835
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, 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_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.9420(2) 0.82888(12) 0.17096(4) 0.0335(3) Uani 1 4 a d . . .
H0 H 0.9362 0.8813 0.1390 0.040 Uiso 1 4 a calc R . .
O3 O 0.6774(6) 0.8218(4) 0.19082(13) 0.0509(8) Uani 1 4 a d . . .
H3 H 0.6293 0.9128 0.1963 0.076 Uiso 1 4 a calc R . .
O4 O 1.0179(6) 0.6632(4) 0.16291(13) 0.0555(9) Uani 1 4 a d . . .
O5 O 1.0964(6) 0.9313(3) 0.20372(10) 0.0433(8) Uani 1 4 a d . . .
N1 N 0.7636(6) 0.4167(4) 0.19841(11) 0.0334(8) Uani 1 4 a d . . .
H1A H 0.7729 0.4253 0.2307 0.050 Uiso 1 4 a calc R . .
H1B H 0.8277 0.5032 0.1846 0.050 Uiso 1 4 a calc R . .
H1C H 0.8441 0.3302 0.1887 0.050 Uiso 1 4 a calc R . .
N2 N 0.9544(7) 0.2996(5) 0.04711(12) 0.0488(10) Uani 1 4 a d . . .
H2 H 1.0844 0.3146 0.0306 0.059 Uiso 1 4 a calc R . .
O1 O 0.1968(5) 0.2116(3) 0.18947(12) 0.0380(7) Uani 1 4 a d . . .
H1 H 0.1653 0.1169 0.1939 0.057 Uiso 1 4 a calc R . .
O2 O 0.5685(6) 0.1326(3) 0.20880(11) 0.0417(7) Uani 1 4 a d . . .
C1 C 0.4257(8) 0.2347(4) 0.19570(14) 0.0298(8) Uani 1 4 a d . . .
C2 C 0.5077(7) 0.4023(5) 0.18371(13) 0.0307(9) Uani 1 4 a d . . .
H22 H 0.4118 0.4782 0.2028 0.037 Uiso 1 4 a calc R . .
C3 C 0.4782(7) 0.4415(5) 0.12953(13) 0.0328(9) Uani 1 4 a d . . .
H3A H 0.3126 0.4199 0.1202 0.039 Uiso 1 4 a calc R . .
H3B H 0.5064 0.5550 0.1250 0.039 Uiso 1 4 a calc R . .
C4 C 0.6411(7) 0.3514(5) 0.09617(13) 0.0321(9) Uani 1 4 a d . . .
C5 C 0.6215(6) 0.1897(5) 0.07869(13) 0.0313(9) Uani 1 4 a d . . .
C6 C 0.8258(8) 0.1594(6) 0.04824(13) 0.0378(10) Uani 1 4 a d . . .
C7 C 0.8470(8) 0.4112(6) 0.07573(14) 0.0417(10) Uani 1 4 a d . . .
H7 H 0.9054 0.5141 0.0807 0.050 Uiso 1 4 a calc R . .
C8 C 0.4543(8) 0.0657(5) 0.08489(14) 0.0380(9) Uani 1 4 a d . . .
H8 H 0.3185 0.0804 0.1043 0.046 Uiso 1 4 a calc R . .
C9 C 0.4939(8) -0.0784(6) 0.06182(15) 0.0455(11) Uani 1 4 a d . . .
H9 H 0.3838 -0.1611 0.0661 0.055 Uiso 1 4 a calc R . .
C10 C 0.6959(9) -0.1034(6) 0.03204(16) 0.0503(12) Uani 1 4 a d . . .
H10 H 0.7174 -0.2021 0.0170 0.060 Uiso 1 4 a calc R . .
C11 C 0.8625(8) 0.0161(6) 0.02478(15) 0.0464(12) Uani 1 4 a d . . .
H11 H 0.9956 0.0005 0.0047 0.056 Uiso 1 4 a calc R . .
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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
P P 0.1023 0.0942 '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
_geom_angle_publ_flag
O4 P1 O5 117.62(19) . . ?
O4 P1 O3 106.62(18) . . ?
O5 P1 O3 110.25(19) . . ?
O4 P1 H0 107.3 . . ?
O5 P1 H0 107.3 . . ?
O3 P1 H0 107.3 . . ?
P1 O3 H3 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C7 N2 C6 110.2(4) . . ?
C7 N2 H2 124.9 . . ?
C6 N2 H2 124.9 . . ?
C1 O1 H1 109.5 . . ?
O2 C1 O1 124.8(4) . . ?
O2 C1 C2 121.3(4) . . ?
O1 C1 C2 113.9(3) . . ?
N1 C2 C1 107.8(3) . . ?
N1 C2 C3 110.5(3) . . ?
C1 C2 C3 112.2(3) . . ?
N1 C2 H22 108.8 . . ?
C1 C2 H22 108.8 . . ?
C3 C2 H22 108.8 . . ?
C4 C3 C2 115.0(3) . . ?
C4 C3 H3A 108.5 . . ?
C2 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
C2 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C7 C4 C5 105.7(4) . . ?
C7 C4 C3 125.0(4) . . ?
C5 C4 C3 129.4(4) . . ?
C8 C5 C6 117.7(4) . . ?
C8 C5 C4 134.8(4) . . ?
C6 C5 C4 107.5(4) . . ?
N2 C6 C11 131.0(4) . . ?
N2 C6 C5 105.9(4) . . ?
C11 C6 C5 123.0(4) . . ?
N2 C7 C4 110.6(4) . . ?
N2 C7 H7 124.7 . . ?
C4 C7 H7 124.7 . . ?
C9 C8 C5 119.0(4) . . ?
C9 C8 H8 120.5 . . ?
C5 C8 H8 120.5 . . ?
C8 C9 C10 121.7(4) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C11 C10 C9 120.8(4) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C6 C11 C10 117.8(4) . . ?
C6 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
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
P1 O4 1.464(3) . ?
P1 O5 1.508(3) . ?
P1 O3 1.566(3) . ?
P1 H0 0.9800 . ?
O3 H3 0.8200 . ?
N1 C2 1.479(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N2 C7 1.357(6) . ?
N2 C6 1.372(6) . ?
N2 H2 0.8600 . ?
O1 C1 1.295(5) . ?
O1 H1 0.8200 . ?
O2 C1 1.218(5) . ?
C1 C2 1.510(5) . ?
C2 C3 1.531(5) . ?
C2 H22 0.9800 . ?
C3 C4 1.490(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C7 1.366(6) . ?
C4 C5 1.439(5) . ?
C5 C8 1.401(6) . ?
C5 C6 1.430(5) . ?
C6 C11 1.375(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.378(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.402(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(7) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
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
O3 H3 O2 0.82 1.90 2.713(4) 171.2 1_565
N1 H1A O5 0.89 1.94 2.797(4) 161.1 4_745
N1 H1B O4 0.89 1.80 2.680(5) 167.4 .
N1 H1C O1 0.89 2.19 2.962(4) 144.3 1_655
O1 H1 O5 0.82 1.62 2.440(4) 178.4 1_445
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
_geom_torsion_publ_flag
O2 C1 C2 N1 -8.8(5) . . . . ?
O1 C1 C2 N1 172.9(3) . . . . ?
O2 C1 C2 C3 113.1(4) . . . . ?
O1 C1 C2 C3 -65.3(4) . . . . ?
N1 C2 C3 C4 52.2(4) . . . . ?
C1 C2 C3 C4 -68.1(4) . . . . ?
C2 C3 C4 C7 -101.2(4) . . . . ?
C2 C3 C4 C5 78.7(5) . . . . ?
C7 C4 C5 C8 -178.7(4) . . . . ?
C3 C4 C5 C8 1.4(7) . . . . ?
C7 C4 C5 C6 0.9(4) . . . . ?
C3 C4 C5 C6 -179.0(4) . . . . ?
C7 N2 C6 C11 178.9(4) . . . . ?
C7 N2 C6 C5 1.7(4) . . . . ?
C8 C5 C6 N2 178.1(3) . . . . ?
C4 C5 C6 N2 -1.6(4) . . . . ?
C8 C5 C6 C11 0.7(6) . . . . ?
C4 C5 C6 C11 -179.0(4) . . . . ?
C6 N2 C7 C4 -1.2(5) . . . . ?
C5 C4 C7 N2 0.2(4) . . . . ?
C3 C4 C7 N2 -179.9(4) . . . . ?
C6 C5 C8 C9 0.3(6) . . . . ?
C4 C5 C8 C9 179.8(4) . . . . ?
C5 C8 C9 C10 -0.6(6) . . . . ?
C8 C9 C10 C11 0.0(7) . . . . ?
N2 C6 C11 C10 -178.0(4) . . . . ?
C5 C6 C11 C10 -1.2(6) . . . . ?
C9 C10 C11 C6 0.9(7) . . . . ?
