#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/34/2003480.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_2003480
loop_
_publ_author_name
'Lis, T.'
'Jerzykiewicz, L. B.'
_publ_section_title
;
 Potassium <small>D</small>-3-Phosphoglycerate and Cyclohexylammonium
 <small>D</small>-3-Phosphoglycerate Hydrate
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1001
_journal_page_last               1005
_journal_paper_doi               10.1107/S0108270194010474
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         '(C6 H14 N) 1+ , (C3 H6 O7 P) 1- , H2 O'
_chemical_formula_sum            'C9 H22 N O8 P'
_chemical_formula_weight         303.25
_chemical_name_systematic
;
Cyclohexylammonium D-3-phosphoglycerate monohydrate
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.332(6)
_cell_length_b                   22.406(11)
_cell_length_c                   5.783(3)
_cell_measurement_reflns_used    '52         [25]'
_cell_measurement_temperature    '85(2)      [292(1)]'
_cell_measurement_theta_max      '12         [16]'
_cell_measurement_theta_min      '10         [10]'
_cell_volume                     1468.3(13)
_computing_cell_refinement       'Kuma KM4 software'
_computing_data_collection       'Kuma KM4 software (Kuma, 1987)'
_computing_data_reduction        'Kuma KM4 software'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      85(2)
_diffrn_measurement_device       'Kuma KM4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4050
_diffrn_reflns_theta_max         30
_diffrn_reflns_theta_min         2
_diffrn_standards_decay_%        3
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.220
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.372(2)
_exptl_crystal_density_meas      '  --       [1.36]'
_exptl_crystal_density_method    'flotation in C~6~H~5~Cl/CCl~4~'
_exptl_crystal_description       'platy shape'
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.243
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.061
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         '2667 icluding 1648 Friedel pairs'
_refine_ls_number_restraints     8
_refine_ls_restrained_S_obs      1.059
_refine_ls_R_factor_obs          0.0433
_refine_ls_shift/esd_max         -0.117
_refine_ls_shift/esd_mean        0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;calc w = 1/[\s^2^(F~o~^2^)+(0.064P)^2^+0.32P]
where P = (F~o~^2^+2F~c~^2^)/3
;
_refine_ls_wR_factor_obs         0.1037
_reflns_number_observed          2667
_reflns_number_total             3551
_reflns_observed_criterion       >2\s(I)
_cod_data_source_file            mu1133.cif
_cod_data_source_block           C9H22NO8P
_cod_original_cell_volume        '1468.3(13)  [1499(3)]'
_cod_database_code               2003480
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_occupancy
_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_flag
_atom_site_refinement_flags
_atom_site_disorder_group
P 1 0.05405(6) 0.24508(3) 0.17515(11) 0.0177(2) Uani d . .
O(1) 1 0.3855(2) 0.12668(10) -0.0680(4) 0.0254(5) Uani d D .
O(11) 1 0.3259(2) 0.16392(10) -0.4093(4) 0.0274(5) Uani d . .
O(2) 1 0.1038(2) 0.11975(10) -0.3497(4) 0.0277(5) Uani d D .
O(3) 1 0.1406(2) 0.20571(9) 0.0185(4) 0.0200(5) Uani d . .
O(31) 1 0.0741(2) 0.30801(9) 0.0973(4) 0.0222(5) Uani d . .
O(32) 1 -0.0745(2) 0.22332(10) 0.1111(4) 0.0206(5) Uani d D .
O(33) 1 0.0727(2) 0.23160(9) 0.4266(3) 0.0226(5) Uani d . .
O(4) 1 -0.1260(2) 0.23767(10) -0.3121(4) 0.0242(4) Uani d D .
C(1) 1 0.3066(3) 0.13780(13) -0.2319(5) 0.0192(6) Uani d . .
C(2) 1 0.1849(3) 0.11324(13) -0.1676(6) 0.0223(6) Uani d . .
C(3) 1 0.1432(3) 0.14197(14) 0.0537(6) 0.0235(7) Uani d . .
N 1 0.2061(2) 0.31417(10) 0.6898(5) 0.0182(5) Uani d D .
C(4) 0.434(6) 0.2555(9) 0.3740(5) 0.6295(16) 0.022(2) Uani d P 1
C(5) 0.434(6) 0.2950(8) 0.4060(4) 0.8502(14) 0.026(2) Uani d P 1
C(6) 0.434(6) 0.3471(9) 0.4666(5) 0.7803(18) 0.039(3) Uani d P 1
C(7) 0.434(6) 0.2625(14) 0.5027(5) 0.6351(18) 0.038(3) Uani d P 1
C(8) 0.434(6) 0.2225(10) 0.4677(4) 0.4219(14) 0.042(2) Uani d P 1
C(9) 0.434(6) 0.1688(9) 0.4071(4) 0.4943(17) 0.036(2) Uani d P 1
C(41) 0.566(6) 0.2092(8) 0.3758(4) 0.5873(14) 0.022(2) Uani d P 2
C(51) 0.566(6) 0.3072(8) 0.4120(4) 0.7074(24) 0.065(4) Uani d P 2
C(61) 0.566(6) 0.3154(9) 0.4760(5) 0.6089(23) 0.066(4) Uani d P 2
C(71) 0.566(6) 0.1946(10) 0.5057(5) 0.6378(20) 0.055(3) Uani d P 2
C(81) 0.566(6) 0.1032(7) 0.4702(4) 0.4987(16) 0.050(2) Uani d P 2
C(91) 0.566(6) 0.0963(6) 0.4065(3) 0.6014(14) 0.039(2) Uani d P 2
H(1) 1 0.458(2) 0.1496(14) -0.074(7) 0.032(10) Uiso d D .
H(20) 1 0.116(5) 0.1613(7) -0.390(8) 0.061(15) Uiso d D .
H(32) 1 -0.100(5) 0.2338(23) -0.044(4) 0.077(18) Uiso d D .
H(40) 1 -0.156(5) 0.2782(10) -0.313(11) 0.084(19) Uiso d D .
H(401) 1 -0.052(2) 0.2319(17) -0.394(6) 0.041(12) Uiso d D .
H(11) 1 0.278(2) 0.2900(15) 0.724(7) 0.040(11) Uiso d D .
H(12) 1 0.166(5) 0.2852(19) 0.584(8) 0.084(18) Uiso d D .
H(13) 1 0.163(3) 0.3118(15) 0.841(3) 0.030(9) Uiso d D .
H(2) 1 0.194 0.0696 -0.137 0.027 Uiso calc R .
H(3) 1 0.063 0.1273 0.094 0.028 Uiso calc R .
H(3') 1 0.197 0.1319 0.182 0.028 Uiso calc R .
H(4) 0.434(6) 0.327 0.3677 0.530 0.026 Uiso calc PR 1
H(5) 0.434(6) 0.355 0.3818 0.932 0.031 Uiso calc PR 1
H(50) 0.434(6) 0.227 0.4118 0.955 0.031 Uiso calc PR 1
H(6) 0.434(6) 0.367 0.4894 0.921 0.047 Uiso calc PR 1
H(60) 0.434(6) 0.421 0.4600 0.692 0.047 Uiso calc PR 1
H(7) 0.434(6) 0.301 0.5401 0.585 0.046 Uiso calc PR 1
H(70) 0.434(6) 0.193 0.5135 0.729 0.046 Uiso calc PR 1
H(8) 0.434(6) 0.291 0.4609 0.318 0.051 Uiso calc PR 1
H(80) 0.434(6) 0.163 0.4912 0.336 0.051 Uiso calc PR 1
H(9) 0.434(6) 0.097 0.4137 0.588 0.043 Uiso calc PR 1
H(90) 0.434(6) 0.147 0.3839 0.355 0.043 Uiso calc PR 1
H(41) 0.566(6) 0.230 0.3719 0.420 0.026 Uiso calc PR 2
H(51) 0.566(6) 0.384 0.3915 0.686 0.078 Uiso calc PR 2
H(510) 0.566(6) 0.291 0.4139 0.875 0.078 Uiso calc PR 2
H(61) 0.566(6) 0.376 0.4990 0.693 0.079 Uiso calc PR 2
H(610) 0.566(6) 0.337 0.4747 0.443 0.079 Uiso calc PR 2
H(71) 0.566(6) 0.198 0.5474 0.581 0.066 Uiso calc PR 2
H(710) 0.566(6) 0.172 0.5063 0.803 0.066 Uiso calc PR 2
H(81) 0.566(6) 0.127 0.4683 0.334 0.060 Uiso calc PR 2
H(810) 0.566(6) 0.025 0.4899 0.508 0.060 Uiso calc PR 2
H(91) 0.566(6) 0.071 0.4090 0.765 0.047 Uiso calc PR 2
H(910) 0.566(6) 0.036 0.3833 0.516 0.047 Uiso calc PR 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0033 0.001
H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.000
N N 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0061 0.003
O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0106 0.006
P P 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.1023 0.094
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
O(31) P O(3) 104.8(2) yes
O(32) P O(3) 105.2(2) yes
O(33) P O(3) 110.6(2) yes
O(31) P O(32) 111.1(2) yes
O(31) P O(33) 117.3(2) yes
O(32) P O(33) 107.2(2) yes
C(3) O(3) P 118.6(2) yes
O(3) C(3) C(2) 108.0(2) yes
C(3) C(2) C(1) 109.6(2) yes
O(2) C(2) C(3) 112.7(2) yes
O(2) C(2) C(1) 111.7(2) yes
O(1) C(1) C(2) 111.5(2) yes
O(11) C(1) C(2) 123.2(3) yes
O(11) C(1) O(1) 125.4(3) yes
C(9) C(4) N 109.2(7) ?
C(9) C(4) C(5) 114.0(9) ?
N C(4) C(5) 109.6(7) ?
C(4) C(5) C(6) 107.9(7) ?
C(7) C(6) C(5) 112.1(8) ?
C(6) C(7) C(8) 111.2(9) ?
C(7) C(8) C(9) 110.4(7) ?
C(4) C(9) C(8) 109.1(8) ?
C(91) C(41) N 113.1(6) ?
C(91) C(41) C(51) 111.1(7) ?
N C(41) C(51) 108.8(6) ?
C(41) C(51) C(61) 111.4(7) ?
C(71) C(61) C(51) 108.0(8) ?
C(61) C(71) C(81) 108.7(8) ?
C(71) C(81) C(91) 108.1(7) ?
C(41) C(91) C(81) 111.7(6) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
P O(3) 1.600(2) yes
P O(31) 1.497(2) yes
P O(33) 1.500(2) yes
P O(32) 1.580(2) yes
C(3) O(3) 1.443(4) yes
C(2) C(3) 1.509(4) yes
C(1) C(2) 1.531(4) yes
C(2) O(2) 1.405(4) yes
C(1) O(1) 1.327(4) yes
C(1) O(11) 1.201(3) yes
N C(4) 1.494(10) ?
N C(41) 1.503(8) ?
C(4) C(9) 1.458(13) ?
C(4) C(5) 1.530(11) ?
C(5) C(6) 1.535(12) ?
C(6) C(7) 1.509(16) ?
C(7) C(8) 1.530(13) ?
C(8) C(9) 1.546(11) ?
C(41) C(91) 1.456(9) ?
C(41) C(51) 1.541(11) ?
C(51) C(61) 1.547(12) ?
C(61) C(71) 1.531(14) ?
C(71) C(81) 1.533(12) ?
C(81) C(91) 1.548(11) ?
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
O(31) P O(3) C(3) 179.3(2) yes
O(32) P O(3) C(3) -63.4(2) yes
O(33) P O(3) C(3) 51.9(2) yes
P O(3) C(3) C(2) 155.5(2) yes
O(2) C(2) C(3) O(3) -67.1(3) yes
O(1) C(1) C(2) O(2) -174.3(2) yes
O(11) C(1) C(2) O(2) 6.0(4) yes
O(1) C(1) C(2) C(3) 60.1(3) yes
O(11) C(1) C(2) C(3) -119.7(3) yes
C(1) C(2) C(3) O(3) 58.0(3) yes
C(41) N C(4) C(9) -1.1(11) no
C(41) N C(4) C(5) 125(2) no
C(9) C(4) C(5) C(6) -58.3(10) no
N C(4) C(5) C(6) 179.0(7) no
C(4) C(5) C(6) C(7) 54.3(10) no
C(5) C(6) C(7) C(8) -55.3(11) no
C(6) C(7) C(8) C(9) 55.2(13) no
N C(4) C(9) C(8) -177.2(7) no
C(5) C(4) C(9) C(8) 59.9(10) no
C(7) C(8) C(9) C(4) -56.8(13) no
C(4) N C(41) C(91) -143(2) no
C(4) N C(41) C(51) -19.4(13) no
C(91) C(41) C(51) C(61) -55.1(12) no
N C(41) C(51) C(61) 179.8(8) no
C(41) C(51) C(61) C(71) 57.2(13) no
C(51) C(61) C(71) C(81) -61.7(12) no
C(61) C(71) C(81) C(91) 62.7(10) no
N C(41) C(91) C(81) 178.9(6) no
C(51) C(41) C(91) C(81) 56.2(9) no
C(71) C(81) C(91) C(41) -60.6(9) no
