#------------------------------------------------------------------------------
#$Date: 2015-06-05 10:39:49 +0300 (Fri, 05 Jun 2015) $
#$Revision: 138350 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/03/1520347.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_1520347
loop_
_publ_author_name
'Tizzard, Graham J.'
'Hursthouse, Michael B.'
'Croft, Anna K.'
_publ_section_title
;
 N-((2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-
 phthalamic acid
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              871
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C14 H17 N O8'
_chemical_formula_sum            'C14 H17 N O8'
_chemical_formula_weight         327.29
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.75500(10)
_cell_length_b                   12.4624(3)
_cell_length_c                   24.7840(7)
_cell_measurement_reflns_used    28436
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1468.67(6)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'CAMERON (Watkin, et al., 1993)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 66.0645
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            17643
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.9988
_exptl_absorpt_correction_T_min  0.9758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         1992
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0492
_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)+(0.0053P)²+1.7875P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                1738
_reflns_number_total             1992
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-871.cif
_cod_data_source_block           2009src0683a
_cod_depositor_comments
;
Citation :
Tizzard, Graham J. and Hursthouse, Michael B. and Croft, Anna K. (2009)
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/871)

More at:
http://ecrystals.chem.soton.ac.uk/871/
;
_cod_database_code               1520347
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4034(7) 0.9381(2) 0.82416(11) 0.0162(7) Uani 1 1 d . . .
H1 H 0.5797 0.9595 0.8050 0.019 Uiso 1 1 calc R . .
C2 C 0.3293(7) 0.8220(2) 0.80955(11) 0.0139(6) Uani 1 1 d . . .
H2 H 0.4893 0.7747 0.8205 0.017 Uiso 1 1 calc R . .
C3 C 0.0672(7) 0.7867(2) 0.84001(11) 0.0135(6) Uani 1 1 d . . .
H3 H -0.0932 0.8347 0.8301 0.016 Uiso 1 1 calc R . .
C4 C 0.1261(7) 0.7972(2) 0.90010(11) 0.0153(6) Uani 1 1 d . . .
H4 H 0.2851 0.7489 0.9105 0.018 Uiso 1 1 calc R . .
C5 C 0.2043(7) 0.9144(2) 0.91212(11) 0.0168(7) Uani 1 1 d . . .
H5 H 0.0421 0.9612 0.9018 0.020 Uiso 1 1 calc R . .
C6 C 0.2785(8) 0.9365(2) 0.97060(11) 0.0198(7) Uani 1 1 d . . .
H6A H 0.3371 1.0124 0.9741 0.024 Uiso 1 1 calc R . .
H6B H 0.1083 0.9263 0.9930 0.024 Uiso 1 1 calc R . .
C7 C 0.4615(7) 0.7546(2) 0.71997(11) 0.0149(6) Uani 1 1 d . . .
C8 C 0.4055(7) 0.7668(2) 0.66027(11) 0.0151(6) Uani 1 1 d . . .
C9 C 0.2354(7) 0.6902(2) 0.63562(12) 0.0194(7) Uani 1 1 d . . .
H9 H 0.1671 0.6308 0.6558 0.023 Uiso 1 1 calc R . .
C10 C 0.1662(8) 0.7010(3) 0.58142(12) 0.0244(8) Uani 1 1 d . . .
H10 H 0.0501 0.6488 0.5645 0.029 Uiso 1 1 calc R . .
C11 C 0.2653(8) 0.7871(3) 0.55190(12) 0.0238(8) Uani 1 1 d . . .
H11 H 0.2155 0.7944 0.5150 0.029 Uiso 1 1 calc R . .
C12 C 0.4370(8) 0.8629(3) 0.57610(12) 0.0232(8) Uani 1 1 d . . .
H12 H 0.5070 0.9216 0.5556 0.028 Uiso 1 1 calc R . .
C13 C 0.5073(7) 0.8532(2) 0.63059(12) 0.0165(7) Uani 1 1 d . . .
C14 C 0.6978(8) 0.9342(2) 0.65614(12) 0.0198(7) Uani 1 1 d . . .
N1 N 0.2936(6) 0.81409(19) 0.75118(9) 0.0153(5) Uani 1 1 d D . .
O1 O 0.4457(5) 0.94607(16) 0.88088(8) 0.0164(5) Uani 1 1 d . . .
O2 O 0.1804(5) 1.00312(16) 0.80663(9) 0.0174(5) Uani 1 1 d . . .
H2A H 0.2421 1.0642 0.7986 0.026 Uiso 1 1 calc R . .
O3 O -0.0049(5) 0.67822(16) 0.82760(8) 0.0188(5) Uani 1 1 d . . .
H3A H -0.1041 0.6768 0.7996 0.028 Uiso 1 1 calc R . .
O4 O -0.1197(5) 0.76948(17) 0.93003(8) 0.0202(5) Uani 1 1 d . . .
H4A H -0.0778 0.7242 0.9538 0.030 Uiso 1 1 calc R . .
O5 O 0.4969(6) 0.86972(18) 0.99096(8) 0.0229(5) Uani 1 1 d . . .
H5A H 0.6054 0.8525 0.9657 0.034 Uiso 1 1 calc R . .
O6 O 0.6411(5) 0.69080(16) 0.73719(8) 0.0182(5) Uani 1 1 d . . .
O7 O 0.8105(5) 0.92139(17) 0.69938(9) 0.0225(5) Uani 1 1 d . . .
O8 O 0.7297(8) 1.02134(19) 0.62642(10) 0.0436(8) Uani 1 1 d . . .
H8 H 0.8272 1.0663 0.6434 0.065 Uiso 1 1 calc R . .
H1N H 0.147(7) 0.861(3) 0.7357(15) 0.052 Uiso 1 1 d D . .
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
O2 C1 O1 111.8(2) . .
O2 C1 C2 107.4(3) . .
O1 C1 C2 109.4(2) . .
O2 C1 H1 109.4 . .
O1 C1 H1 109.4 . .
C2 C1 H1 109.4 . .
N1 C2 C3 112.1(3) . .
N1 C2 C1 108.9(2) . .
C3 C2 C1 110.1(2) . .
N1 C2 H2 108.5 . .
C3 C2 H2 108.5 . .
C1 C2 H2 108.5 . .
O3 C3 C4 109.7(2) . .
O3 C3 C2 111.3(2) . .
C4 C3 C2 108.0(2) . .
O3 C3 H3 109.3 . .
C4 C3 H3 109.3 . .
C2 C3 H3 109.3 . .
O4 C4 C3 109.7(3) . .
O4 C4 C5 109.1(2) . .
C3 C4 C5 108.4(2) . .
O4 C4 H4 109.8 . .
C3 C4 H4 109.8 . .
C5 C4 H4 109.8 . .
O1 C5 C6 106.2(3) . .
O1 C5 C4 110.4(2) . .
C6 C5 C4 114.4(2) . .
O1 C5 H5 108.5 . .
C6 C5 H5 108.5 . .
C4 C5 H5 108.5 . .
O5 C6 C5 113.7(3) . .
O5 C6 H6A 108.8 . .
C5 C6 H6A 108.8 . .
O5 C6 H6B 108.8 . .
C5 C6 H6B 108.8 . .
H6A C6 H6B 107.7 . .
O6 C7 N1 124.5(3) . .
O6 C7 C8 121.5(3) . .
N1 C7 C8 113.9(3) . .
C13 C8 C9 120.1(3) . .
C13 C8 C7 122.3(3) . .
C9 C8 C7 117.6(3) . .
C10 C9 C8 119.7(3) . .
C10 C9 H9 120.2 . .
C8 C9 H9 120.2 . .
C11 C10 C9 120.4(3) . .
C11 C10 H10 119.8 . .
C9 C10 H10 119.8 . .
C10 C11 C12 120.1(3) . .
C10 C11 H11 119.9 . .
C12 C11 H11 119.9 . .
C11 C12 C13 120.0(3) . .
C11 C12 H12 120.0 . .
C13 C12 H12 120.0 . .
C8 C13 C12 119.7(3) . .
C8 C13 C14 120.6(3) . .
C12 C13 C14 119.7(3) . .
O7 C14 O8 123.5(3) . .
O7 C14 C13 123.6(3) . .
O8 C14 C13 112.8(3) . .
C7 N1 C2 122.8(3) . .
C7 N1 H1N 122(2) . .
C2 N1 H1N 115(2) . .
C1 O1 C5 113.5(2) . .
C1 O2 H2A 109.5 . .
C3 O3 H3A 109.5 . .
C4 O4 H4A 109.5 . .
C6 O5 H5A 109.5 . .
C14 O8 H8 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O2 1.404(4) .
C1 O1 1.424(3) .
C1 C2 1.532(4) .
C1 H1 1.0000 .
C2 N1 1.460(3) .
C2 C3 1.522(4) .
C2 H2 1.0000 .
C3 O3 1.429(3) .
C3 C4 1.521(4) .
C3 H3 1.0000 .
C4 O4 1.427(4) .
C4 C5 1.536(4) .
C4 H4 1.0000 .
C5 O1 1.440(4) .
C5 C6 1.517(4) .
C5 H5 1.0000 .
C6 O5 1.423(4) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 O6 1.243(4) .
C7 N1 1.336(4) .
C7 C8 1.511(4) .
C8 C13 1.390(4) .
C8 C9 1.393(4) .
C9 C10 1.390(4) .
C9 H9 0.9500 .
C10 C11 1.382(4) .
C10 H10 0.9500 .
C11 C12 1.385(5) .
C11 H11 0.9500 .
C12 C13 1.397(4) .
C12 H12 0.9500 .
C13 C14 1.497(5) .
C14 O7 1.209(4) .
C14 O8 1.321(4) .
N1 H1N 0.985(19) .
O2 H2A 0.8400 .
O3 H3A 0.8400 .
O4 H4A 0.8400 .
O5 H5A 0.8400 .
O8 H8 0.8400 .
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
O2 H2A O6 0.84 1.89 2.715(3) 165.7 3_656
O3 H3A O6 0.84 1.97 2.807(3) 172.6 1_455
O4 H4A O5 0.84 1.84 2.674(3) 176.0 4_467
O5 H5A O4 0.84 1.89 2.677(3) 156.3 1_655
O8 H8 O3 0.84 1.78 2.614(3) 170.3 3_656
N1 H1N O7 0.985(19) 1.99(2) 2.952(3) 166(4) 1_455
