#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/80/2018070.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_2018070
loop_
_publ_author_name
'Ślepokura, Katarzyna'
'Mitaszewska, Irmina'
_publ_section_title
;
 Acidic and anionic forms of 1,3-cyclic dihydroxyacetone phosphate
 (cDHAP) dimethyl acetal
;
_journal_coeditor_code           MX3045
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o161
_journal_page_last               o165
_journal_paper_doi               10.1107/S0108270111011723
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C6 H14 N + , C5 H10 O6 P - , H2 O'
_chemical_formula_moiety         'C6 H14 N +, C5 H10 O6 P -, H2 O'
_chemical_formula_sum            'C11 H26 N O7 P'
_chemical_formula_weight         315.30
_chemical_name_common
;
cyclic dihydroxyacetone phosphate (cDHAP) dimethyl acetal
cyclohexylammonium salt monohydrate
;
_chemical_name_systematic
;
cyclohexylammonium 5,5-dimethoxy-2-oxo-1,3,2-dioxaphosphinane-2-olate
monohydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                102.48(3)
_cell_angle_beta                 92.58(3)
_cell_angle_gamma                99.96(3)
_cell_formula_units_Z            2
_cell_length_a                   7.064(2)
_cell_length_b                   8.475(4)
_cell_length_c                   13.966(6)
_cell_measurement_reflns_used    8262
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.94
_cell_measurement_theta_min      2.93
_cell_volume                     801.1(6)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'XP (Bruker, 1998)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type
;
Kuma KM4CCD κ-geometry diffractometer with a Sapphire CCD camera
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13552
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.176
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4519
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0606P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0942
_reflns_number_gt                3579
_reflns_number_total             4519
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            mx3045.cif
_cod_data_source_block           5i
_cod_database_code               2018070
_cod_database_fobs_code          2018070
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.31711(4) 0.28342(3) 0.66395(2) 0.01842(8) Uani d . 1 . .
O O1 0.26362(10) 0.33074(9) 0.77583(5) 0.01893(16) Uani d . 1 . .
O O21 0.71792(11) 0.38258(10) 0.91694(6) 0.02296(17) Uani d . 1 . .
O O22 0.48544(11) 0.14207(9) 0.86906(6) 0.02146(17) Uani d . 1 . .
O O3 0.47730(11) 0.17337(9) 0.67189(6) 0.02163(17) Uani d . 1 . .
O O4 0.40440(11) 0.43564(9) 0.63354(6) 0.02284(17) Uani d . 1 . .
O O5 0.14713(12) 0.17229(10) 0.60536(6) 0.02596(18) Uani d . 1 . .
C C1 0.42506(14) 0.40898(13) 0.84599(8) 0.0189(2) Uani d . 1 . .
H H1A 0.3798 0.4392 0.9124 0.023 Uiso calc R 1 . .
H H1B 0.4901 0.5109 0.8286 0.023 Uiso calc R 1 . .
C C2 0.56685(14) 0.29200(12) 0.84642(8) 0.0178(2) Uani d . 1 . .
C C3 0.63690(15) 0.24372(14) 0.74398(8) 0.0217(2) Uani d . 1 . .
H H3A 0.7118 0.3423 0.7268 0.026 Uiso calc R 1 . .
H H3B 0.7230 0.1632 0.7442 0.026 Uiso calc R 1 . .
C C4 0.87607(16) 0.29994(16) 0.92631(9) 0.0291(3) Uani d . 1 . .
H H4A 0.8263 0.1847 0.9266 0.044 Uiso calc R 1 . .
H H4B 0.9550 0.3536 0.9880 0.044 Uiso calc R 1 . .
H H4C 0.9551 0.3050 0.8708 0.044 Uiso calc R 1 . .
C C5 0.38159(17) 0.15534(15) 0.95452(9) 0.0275(2) Uani d . 1 . .
H H5A 0.4607 0.2337 1.0098 0.041 Uiso calc R 1 . .
H H5B 0.3505 0.0474 0.9707 0.041 Uiso calc R 1 . .
H H5C 0.2620 0.1941 0.9420 0.041 Uiso calc R 1 . .
N N1 -0.10007(13) 0.17323(11) 0.44695(7) 0.02130(19) Uani d . 1 . .
H H1N -0.0066 0.1884 0.4968 0.032 Uiso calc R 1 . .
H H2N -0.1497 0.0640 0.4257 0.032 Uiso calc R 1 . .
H H3N -0.1956 0.2278 0.4689 0.032 Uiso calc R 1 . .
C C11 -0.01544(15) 0.23810(13) 0.36398(8) 0.0201(2) Uani d . 1 . .
H H11 0.0384 0.3581 0.3883 0.024 Uiso calc R 1 . .
C C12 0.14708(16) 0.15079(15) 0.32848(9) 0.0254(2) Uani d . 1 . .
H H12A 0.0973 0.0310 0.3071 0.030 Uiso calc R 1 . .
H H12B 0.2484 0.1693 0.3831 0.030 Uiso calc R 1 . .
C C13 0.23337(17) 0.21488(16) 0.24288(10) 0.0299(3) Uani d . 1 . .
H H13A 0.2968 0.3316 0.2666 0.036 Uiso calc R 1 . .
H H13B 0.3330 0.1514 0.2176 0.036 Uiso calc R 1 . .
C C14 0.08025(18) 0.20070(17) 0.15982(9) 0.0311(3) Uani d . 1 . .
H H14A 0.0302 0.0830 0.1296 0.037 Uiso calc R 1 . .
H H14B 0.1391 0.2526 0.1085 0.037 Uiso calc R 1 . .
C C15 -0.08662(18) 0.28347(16) 0.19673(9) 0.0294(3) Uani d . 1 . .
H H15A -0.0399 0.4036 0.2189 0.035 Uiso calc R 1 . .
H H15B -0.1881 0.2642 0.1421 0.035 Uiso calc R 1 . .
C C16 -0.17213(16) 0.21707(14) 0.28154(8) 0.0224(2) Uani d . 1 . .
H H16A -0.2749 0.2770 0.3065 0.027 Uiso calc R 1 . .
H H16B -0.2303 0.0991 0.2581 0.027 Uiso calc R 1 . .
O O1W 0.70098(13) 0.41696(11) 0.51321(7) 0.02652(19) Uani d . 1 . .
H H1W 0.608(2) 0.419(2) 0.5482(13) 0.040 Uiso d . 1 . .
H H2W 0.674(2) 0.460(2) 0.4674(13) 0.040 Uiso d . 1 . .
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'
N N 0.0061 0.0033 '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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O5 P1 O4 . . 119.97(5) ?
O5 P1 O3 . . 106.58(6) ?
O4 P1 O3 . . 109.74(5) ?
O5 P1 O1 . . 107.69(5) ?
O4 P1 O1 . . 109.24(5) ?
O3 P1 O1 . . 102.13(5) ?
C1 O1 P1 . . 114.57(7) ?
C2 O21 C4 . . 114.41(9) ?
C2 O22 C5 . . 115.66(9) ?
C3 O3 P1 . . 116.69(7) ?
O1 C1 C2 . . 109.64(9) ?
O1 C1 H1A . . 109.7 ?
C2 C1 H1A . . 109.7 ?
O1 C1 H1B . . 109.7 ?
C2 C1 H1B . . 109.7 ?
H1A C1 H1B . . 108.2 ?
O22 C2 O21 . . 111.81(9) ?
O22 C2 C1 . . 113.65(9) ?
O21 C2 C1 . . 104.21(9) ?
O22 C2 C3 . . 105.01(9) ?
O21 C2 C3 . . 112.14(9) ?
C1 C2 C3 . . 110.21(9) ?
O3 C3 C2 . . 110.72(9) ?
O3 C3 H3A . . 109.5 ?
C2 C3 H3A . . 109.5 ?
O3 C3 H3B . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 108.1 ?
O21 C4 H4A . . 109.5 ?
O21 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
O21 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
O22 C5 H5A . . 109.5 ?
O22 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
O22 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C11 N1 H1N . . 109.5 ?
C11 N1 H2N . . 109.5 ?
H1N N1 H2N . . 109.5 ?
C11 N1 H3N . . 109.5 ?
H1N N1 H3N . . 109.5 ?
H2N N1 H3N . . 109.5 ?
N1 C11 C12 . . 109.86(9) ?
N1 C11 C16 . . 109.67(9) ?
C12 C11 C16 . . 111.46(10) ?
N1 C11 H11 . . 108.6 ?
C12 C11 H11 . . 108.6 ?
C16 C11 H11 . . 108.6 ?
C11 C12 C13 . . 110.32(10) ?
C11 C12 H12A . . 109.6 ?
C13 C12 H12A . . 109.6 ?
C11 C12 H12B . . 109.6 ?
C13 C12 H12B . . 109.6 ?
H12A C12 H12B . . 108.1 ?
C14 C13 C12 . . 111.64(10) ?
C14 C13 H13A . . 109.3 ?
C12 C13 H13A . . 109.3 ?
C14 C13 H13B . . 109.3 ?
C12 C13 H13B . . 109.3 ?
H13A C13 H13B . . 108.0 ?
C13 C14 C15 . . 111.53(11) ?
C13 C14 H14A . . 109.3 ?
C15 C14 H14A . . 109.3 ?
C13 C14 H14B . . 109.3 ?
C15 C14 H14B . . 109.3 ?
H14A C14 H14B . . 108.0 ?
C16 C15 C14 . . 111.35(10) ?
C16 C15 H15A . . 109.4 ?
C14 C15 H15A . . 109.4 ?
C16 C15 H15B . . 109.4 ?
C14 C15 H15B . . 109.4 ?
H15A C15 H15B . . 108.0 ?
C11 C16 C15 . . 109.89(10) ?
C11 C16 H16A . . 109.7 ?
C15 C16 H16A . . 109.7 ?
C11 C16 H16B . . 109.7 ?
C15 C16 H16B . . 109.7 ?
H16A C16 H16B . . 108.2 ?
H1W O1W H2W . . 106.0(15) ?
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
P1 O5 . 1.4784(11) ?
P1 O4 . 1.4866(10) ?
P1 O3 . 1.6004(10) ?
P1 O1 . 1.6061(10) ?
O1 C1 . 1.4343(14) ?
O21 C2 . 1.4118(13) ?
O21 C4 . 1.4328(15) ?
O22 C2 . 1.4080(13) ?
O22 C5 . 1.4229(15) ?
O3 C3 . 1.4304(14) ?
C1 C2 . 1.5270(15) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 C3 . 1.5297(16) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
N1 C11 . 1.4921(15) ?
N1 H1N . 0.91 ?
N1 H2N . 0.91 ?
N1 H3N . 0.91 ?
C11 C12 . 1.5158(16) ?
C11 C16 . 1.5201(16) ?
C11 H11 . 1.00 ?
C12 C13 . 1.5255(18) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 . 1.5205(18) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C15 . 1.5270(18) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C16 . 1.5230(17) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
O1W H1W . 0.83(2) ?
O1W H2W . 0.83(2) ?
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
_geom_hbond_publ_flag
N1 H1N O5 . 0.91 1.87 2.758(2) 166 no
N1 H2N O5 2_556 0.91 1.96 2.817(2) 157 no
N1 H3N O1W 1_455 0.91 1.87 2.719(2) 154 no
O1W H1W O4 . 0.83(2) 1.92(2) 2.749(2) 176(2) no
O1W H2W O4 2_666 0.83(2) 1.93(2) 2.758(2) 176(2) no
C4 H4C O1 1_655 0.98 2.60 3.534(2) 159 no
C11 H11 O1W 2_666 1.00 2.52 3.416(2) 149 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O5 P1 O1 C1 . . . . 167.33(7) ?
O4 P1 O1 C1 . . . . -60.85(8) ?
O3 P1 O1 C1 . . . . 55.31(8) ?
O5 P1 O3 C3 . . . . -165.65(7) ?
O4 P1 O3 C3 . . . . 63.00(9) ?
O1 P1 O3 C3 . . . . -52.80(8) ?
P1 O1 C1 C2 . . . . -62.20(9) ?
C5 O22 C2 O21 . . . . 67.92(11) ?
C5 O22 C2 C1 . . . . -49.72(12) ?
C5 O22 C2 C3 . . . . -170.24(9) ?
C4 O21 C2 O22 . . . . 60.27(12) ?
C4 O21 C2 C1 . . . . -176.57(8) ?
C4 O21 C2 C3 . . . . -57.38(12) ?
O1 C1 C2 O22 . . . . -58.46(11) ?
O1 C1 C2 O21 . . . . 179.58(7) ?
O1 C1 C2 C3 . . . . 59.08(11) ?
P1 O3 C3 C2 . . . . 56.68(10) ?
O22 C2 C3 O3 . . . . 66.71(11) ?
O21 C2 C3 O3 . . . . -171.66(8) ?
C1 C2 C3 O3 . . . . -56.06(11) ?
N1 C11 C12 C13 . . . . 179.41(9) ?
C16 C11 C12 C13 . . . . 57.64(13) ?
C11 C12 C13 C14 . . . . -55.09(14) ?
C12 C13 C14 C15 . . . . 53.82(15) ?
C13 C14 C15 C16 . . . . -54.52(14) ?
N1 C11 C16 C15 . . . . 179.87(9) ?
C12 C11 C16 C15 . . . . -58.26(13) ?
C14 C15 C16 C11 . . . . 56.21(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654303
