#------------------------------------------------------------------------------
#$Date: 2017-01-30 16:01:18 +0200 (Mon, 30 Jan 2017) $
#$Revision: 191095 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/54/2005411.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_2005411
loop_
_publ_author_name
'Angelova, O.'
'Petrova, R.'
'Radomirska, V.'
'Kolev, T.'
_publ_contact_author
;
     Dr Olyana Angelova
     Bulgarian Academy of Sciences
     CL of Mineralogy and Crystallography
     Rakovski str. 92
     1000 Sofia
     Bulgaria
;
_publ_section_title
;
 Crystalline Complexes Involving Amino Acids. II.
 (R)-({-})-1-Phenylglycinium Hydrogen Squarate Monohydrate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2218
_journal_page_last               2220
_journal_paper_doi               10.1107/S0108270196006452
_journal_volume                  52
_journal_year                    1996
_chemical_formula_iupac          'C8 H10 N O2 1+ , C4 H O4 1- , H2 O'
_chemical_formula_structural
'((C6 H5) C (H) (N H3) C (O) (O H)) (C4 O4 H)'
_chemical_formula_sum            'C12 H13 N O7'
_chemical_formula_weight         283.23
_chemical_melting_point          'over 580 K with decomposition'
_chemical_name_systematic
'Phenylglycinium hydrogen squarate monohydrate'
_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_type_scat_source           'SDP/PDP (Enraf-Nonius, 1985)'
_audit_creation_method
'from SDP files using KAPPA (Macicek, 1992. Unpublished)'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.366(2)
_cell_length_b                   11.066(2)
_cell_length_c                   14.562(2)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    292
_cell_measurement_theta_max      21.12
_cell_measurement_theta_min      20.21
_cell_volume                     1348.1(4)
_computing_data_collection       'CAD-4 (Enraf-Nonius, 1988)'
_computing_data_reduction        'SDP/PDP (Enraf-Nonius, 1985)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'KAPPA (Macíček, 1992)'
_computing_structure_refinement  SDP/PDP
_computing_structure_solution    'SHELXS86 (Sheldrick, 1985)'
_diffrn_ambient_temperature      292
_diffrn_measurement_device       'Enraf-Nonius CAD-4 diffractometer'
_diffrn_measurement_method       'continuous scan profiles'
_diffrn_radiation_monochromator  'graphite (perpendicular mode)'
_diffrn_radiation_source         '2kW fine focus Philips tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.014
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3650
_diffrn_reflns_reduction_process
'F~obs~ = ( I~raw~/LP )^1/2^, where LP = Lorentz-polarization correction'
_diffrn_reflns_theta_max         28.0
_diffrn_reflns_theta_min         0.0
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.10
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.955
_exptl_absorpt_correction_type
'empirical based on \y scans (North, Phillips & Mathews, 1968)'
_exptl_absorpt_process_details   '(North, Phillips and Mathews, 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.348
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.557
_refine_ls_goodness_of_fit_obs   1.112
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    13
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.080
_refine_ls_R_factor_obs          0.045
_refine_ls_shift/esd_max         0.023
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(F) + (0.020F)²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.081
_refine_ls_wR_factor_obs         0.057
_reflns_number_observed          2293
_reflns_number_total             3251
_reflns_observed_criterion       'I > 3.0\s(I)'
_cod_data_source_file            na1238.cif
_cod_data_source_block           LRSA0227
_cod_depositor_comments
;
 Adding the _atom_site_type_symbol data item.

 Antanas Vaitkus,
 2017-01-30

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/[\s^2^(F) + (0.020F)^2^]' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w = 1/[\s^2^(F) +
(0.020F)^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1348.1(8)
_cod_database_code               2005411
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
1/2-x,-y,1/2+z
1/2+x,1/2-y,-z
-x,1/2+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_calc_attached_atom
O11 O 0.5447(2) -0.1522(1) 0.2580(2) 0.0633(5) Uani ?
O12 O 0.5499(2) 0.1326(1) 0.2393(1) 0.0559(5) Uani ?
O13 O 0.1654(2) 0.1440(1) 0.2721(1) 0.0463(4) Uani ?
O14 O 0.1668(2) -0.1470(1) 0.3081(1) 0.0466(4) Uani ?
O1 O -0.2485(3) 0.1741(2) 0.0124(1) 0.0925(7) Uani ?
O2 O -0.2441(2) -0.0069(2) -0.0504(1) 0.0698(5) Uani ?
N N -0.1386(2) 0.1039(2) 0.1731(1) 0.0438(4) Uani ?
OW O -0.1394(2) -0.0906(2) 0.3052(1) 0.0562(4) Uani ?
C11 C 0.4356(2) -0.0692(2) 0.2685(2) 0.0400(5) Uani ?
C12 C 0.4416(2) 0.0578(2) 0.2582(2) 0.0386(5) Uani ?
C13 C 0.2672(2) 0.0646(2) 0.2745(1) 0.0337(4) Uani ?
C14 C 0.2683(2) -0.0690(2) 0.2890(1) 0.0345(4) Uani ?
C1 C -0.2174(3) 0.0696(2) 0.0148(2) 0.0487(6) Uani ?
C2 C -0.1345(2) 0.0123(2) 0.0969(2) 0.0410(5) Uani ?
C3 C 0.0347(2) -0.0253(2) 0.0742(1) 0.0378(5) Uani ?
C4 C 0.0795(3) -0.1453(2) 0.0829(2) 0.0489(6) Uani ?
C5 C 0.2369(3) -0.1783(2) 0.0610(2) 0.0634(7) Uani ?
C6 C 0.3439(3) -0.0934(3) 0.0325(2) 0.0665(7) Uani ?
C7 C 0.2998(3) 0.0257(3) 0.0237(2) 0.0596(7) Uani ?
C8 C 0.1444(3) 0.0590(2) 0.0442(2) 0.0500(6) Uani ?
H11O H 0.4899(38) -0.2373(29) 0.2545(30) 0.0633 Uiso ?
HW1 H -0.0341(39) -0.1108(30) 0.3078(25) 0.0633 Uiso ?
HW2 H -0.1808(32) -0.1439(26) 0.2924(20) 0.0633 Uiso ?
H2O H -0.2735(35) 0.0280(28) -0.0931(23) 0.0633 Uiso ?
HN1 H -0.1283(28) 0.1830(22) 0.1499(17) 0.0633 Uiso N
HN2 H -0.0512(39) 0.0893(28) 0.2133(24) 0.0633 Uiso N
HN3 H -0.2298(30) 0.0968(25) 0.2025(21) 0.0633 Uiso N
H2 H -0.1947(20) -0.0575(15) 0.1202(13) 0.0633 Uiso C2
H4 H 0.0044(23) -0.2043(19) 0.1024(15) 0.0633 Uiso C4
H5 H 0.2694(36) -0.2600(32) 0.0678(26) 0.0633 Uiso C5
H6 H 0.4499(33) -0.1172(27) 0.0178(20) 0.0633 Uiso C6
H7 H 0.3745(36) 0.0841(28) 0.0027(23) 0.0633 Uiso C7
H8 H 0.1132(25) 0.1412(20) 0.0385(15) 0.0633 Uiso C8
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
O 0.008 0.006
N 0.004 0.003
C 0.002 0.002
H 0.000 0.000
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
0 4 4
0 0 6
3 0 3
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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O11 H11O 1 1 109.50(10) no
C1 O2 H2O 1 1 108.6(2) no
C2 N HN1 1 1 111.1(2) no
C2 N HN2 1 1 108.9(2) no
C2 N HN3 1 1 108.7(2) no
HN1 N HN2 1 1 108.0(2) no
HN1 N HN3 1 1 109.6(2) no
HN2 N HN3 1 1 110.6(2) no
HW1 OW HW2 1 1 106.2(2) no
O11 C11 C12 1 1 131.5(2) yes
O11 C11 C14 1 1 135.2(2) yes
C12 C11 C14 1 1 93.2(2) yes
O12 C12 C11 1 1 134.7(2) yes
O12 C12 C13 1 1 135.4(2) yes
C11 C12 C13 1 1 89.9(2) yes
O13 C13 C12 1 1 135.9(2) yes
O13 C13 C14 1 1 135.9(2) yes
C12 C13 C14 1 1 88.10(10) yes
O14 C14 C11 1 1 135.6(2) yes
O14 C14 C13 1 1 135.6(2) yes
C11 C14 C13 1 1 88.70(10) yes
O1 C1 O2 1 1 125.4(3) yes
O1 C1 C2 1 1 122.0(2) yes
O2 C1 C2 1 1 112.5(2) yes
N C2 C1 1 1 106.8(2) yes
N C2 C3 1 1 111.6(2) yes
N C2 H2 1 1 105.3(2) no
C1 C2 C3 1 1 111.7(2) yes
C1 C2 H2 1 1 111.5(2) no
C3 C2 H2 1 1 109.8(2) no
C2 C3 C4 1 1 119.8(2) no
C2 C3 C8 1 1 120.3(2) no
C4 C3 C8 1 1 119.8(2) no
C3 C4 C5 1 1 118.9(2) no
C3 C4 H4 1 1 120.5(2) no
C5 C4 H4 1 1 120.6(2) no
C4 C5 C6 1 1 120.4(2) no
C4 C5 H5 1 1 119.5(3) no
C6 C5 H5 1 1 120.0(3) no
C5 C6 C7 1 1 120.9(3) no
C5 C6 H6 1 1 119.4(3) no
C7 C6 H6 1 1 119.7(3) no
C6 C7 C8 1 1 119.2(3) no
C6 C7 H7 1 1 120.5(3) no
C8 C7 H7 1 1 120.3(3) no
C3 C8 C7 1 1 120.8(2) no
C3 C8 H8 1 1 119.6(2) no
C7 C8 H8 1 1 119.6(2) no
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
O11 C11 1 1.304(2) yes
O11 H11O 1 1.0490(10) no
O12 C12 1 1.257(2) yes
O13 C13 1 1.223(2) yes
O14 C14 1 1.242(2) yes
O1 C1 1 1.186(3) yes
O2 C1 1 1.292(3) yes
O2 H2O 1 0.773(2) no
N C2 1 1.503(3) yes
N HN1 1 0.943(2) no
N HN2 1 0.951(2) no
N HN3 1 0.879(2) no
OW HW1 1 0.910(2) no
OW HW2 1 0.710(2) no
C11 C12 1 1.414(3) yes
C11 C14 1 1.431(3) yes
C12 C13 1 1.481(3) yes
C13 C14 1 1.494(3) yes
C1 C2 1 1.521(3) yes
C2 C3 1 1.512(3) yes
C2 H2 1 0.984(2) no
C3 C4 1 1.385(3) yes
C3 C8 1 1.380(3) yes
C4 C5 1 1.403(4) yes
C4 H4 1 0.950(2) no
C5 C6 1 1.362(4) yes
C5 H5 1 0.950(3) no
C6 C7 1 1.374(4) yes
C6 H6 1 0.950(3) no
C7 C8 1 1.385(4) yes
C7 H7 1 0.950(3) no
C8 H8 1 0.950(2) no
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
O1 C1 C2 N 12.2(3) no
O1 C1 C2 C3 -110.1(3) no
O2 C1 C2 N -169.7(2) no
O2 C1 C2 C3 68.0(2) no
N C2 C3 C4 119.9(2) no
N C2 C3 C8 -60.7(3) no
C1 C2 C3 C4 -120.6(2) no
C1 C2 C3 C8 58.8(3) no
