#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:11:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178424 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/45/4024561.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_4024561
loop_
_publ_author_name
'Daniel Sejer Pedersen'
'Tony V. Robinson'
'Dennis K. Taylor'
'Edward R. T. Tiekink'
_publ_section_title
;
A Concise Route to Branched Erythrono-γ-lactones. Synthesis of the
Leaf-Closing Substance Potassium
(\+-)-(2R,3R)-2,3,4-Trihydroxy-2-methylbutanoate
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4400
_journal_page_last               4403
_journal_paper_doi               10.1021/jo900392y
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C14 H20 O4'
_chemical_formula_sum            'C14 H20 O4'
_chemical_formula_weight         252.30
_chemical_name_systematic
; 
 ? 
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.781(4)
_cell_angle_beta                 96.664(5)
_cell_angle_gamma                118.379(11)
_cell_formula_units_Z            2
_cell_length_a                   6.374(3)
_cell_length_b                   6.410(3)
_cell_length_c                   16.590(4)
_cell_measurement_reflns_used    476
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.5
_cell_volume                     589.4(4)
_computing_cell_refinement       CrystalClear
_computing_data_collection
'CrystalClear (Rigaku Americas Corporation, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics
'ORTEPII (Johnson, 1976) & DIAMOND (Brandenburg, 2006)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  AFC12κ/SATURN724
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.013
_diffrn_reflns_av_sigmaI/netI    0.011
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4250
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.17
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         1978
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.09
_refine_ls_R_factor_all          0.035
_refine_ls_R_factor_gt           0.034
_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)+(0.0335P)²+0.2781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.083
_refine_ls_wR_factor_ref         0.084
_reflns_number_gt                1928
_reflns_number_total             1978
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo900392y_si_005.cif
_cod_data_source_block           shelxl
_cod_database_code               4024561
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O1 O 0.50841(17) 0.11061(16) 0.41518(6) 0.0253(2) Uani 1 1 d . . .
O2 O 0.49675(17) 0.44538(17) 0.39525(6) 0.0263(2) Uani 1 1 d . . .
O3 O 1.00084(17) 0.63285(16) 0.37827(5) 0.0233(2) Uani 1 1 d D . .
H3O H 1.0021 0.6563 0.4285 0.035 Uiso 1 1 d D . .
O4 O 1.06704(17) 0.30646(19) 0.45966(5) 0.0267(2) Uani 1 1 d D . .
H4O H 1.2052 0.3625 0.4461 0.040 Uiso 1 1 d D . .
C2 C 0.5955(2) 0.3256(2) 0.38845(7) 0.0191(3) Uani 1 1 d . . .
C3 C 0.8289(2) 0.3946(2) 0.35210(7) 0.0176(3) Uani 1 1 d . . .
C4 C 0.9016(2) 0.2098(2) 0.38632(7) 0.0203(3) Uani 1 1 d . . .
H4 H 0.9688 0.1520 0.3447 0.024 Uiso 1 1 calc R . .
C5 C 0.6665(3) 0.0084(2) 0.40548(8) 0.0250(3) Uani 1 1 d . . .
H5A H 0.5929 -0.1215 0.3604 0.030 Uiso 1 1 calc R . .
H5B H 0.6955 -0.0572 0.4563 0.030 Uiso 1 1 calc R . .
C30 C 0.7826(2) 0.3759(2) 0.25714(7) 0.0151(3) Uani 1 1 d . . .
C31 C 0.5998(2) 0.1209(2) 0.21923(7) 0.0168(3) Uani 1 1 d . . .
H31A H 0.6594 0.0095 0.2363 0.020 Uiso 1 1 calc R . .
H31B H 0.4436 0.0703 0.2391 0.020 Uiso 1 1 calc R . .
C32 C 0.5635(2) 0.1118(2) 0.12571(7) 0.0180(3) Uani 1 1 d . . .
H32 H 0.4454 -0.0545 0.1020 0.022 Uiso 1 1 calc R . .
C33 C 0.8048(2) 0.1878(2) 0.09481(8) 0.0192(3) Uani 1 1 d . . .
H33A H 0.8675 0.0782 0.1112 0.023 Uiso 1 1 calc R . .
H33B H 0.7814 0.1800 0.0345 0.023 Uiso 1 1 calc R . .
C34 C 0.9861(2) 0.4428(2) 0.13092(7) 0.0179(3) Uani 1 1 d . . .
H34 H 1.1434 0.4921 0.1108 0.021 Uiso 1 1 calc R . .
C35 C 1.0237(2) 0.4525(2) 0.22428(7) 0.0170(3) Uani 1 1 d . . .
H35A H 1.1424 0.6167 0.2477 0.020 Uiso 1 1 calc R . .
H35B H 1.0889 0.3453 0.2412 0.020 Uiso 1 1 calc R . .
C36 C 0.6863(2) 0.5461(2) 0.22862(8) 0.0180(3) Uani 1 1 d . . .
H36A H 0.5315 0.5008 0.2488 0.022 Uiso 1 1 calc R . .
H36B H 0.8027 0.7111 0.2518 0.022 Uiso 1 1 calc R . .
C37 C 0.6483(2) 0.5355(2) 0.13536(8) 0.0188(3) Uani 1 1 d . . .
H37 H 0.5849 0.6458 0.1183 0.023 Uiso 1 1 calc R . .
C38 C 0.4665(2) 0.2804(2) 0.09894(8) 0.0201(3) Uani 1 1 d . . .
H38A H 0.3095 0.2311 0.1180 0.024 Uiso 1 1 calc R . .
H38B H 0.4416 0.2734 0.0387 0.024 Uiso 1 1 calc R . .
C39 C 0.8890(2) 0.6117(2) 0.10407(8) 0.0200(3) Uani 1 1 d . . .
H39A H 1.0062 0.7773 0.1264 0.024 Uiso 1 1 calc R . .
H39B H 0.8654 0.6058 0.0438 0.024 Uiso 1 1 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'
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
C2 O1 C5 111.11(10) . . ?
C3 O3 H3O 108.1 . . ?
C4 O4 H4O 106.2 . . ?
O2 C2 O1 121.15(12) . . ?
O2 C2 C3 127.12(12) . . ?
O1 C2 C3 111.71(10) . . ?
O3 C3 C2 110.48(10) . . ?
O3 C3 C30 106.49(10) . . ?
C2 C3 C30 111.38(10) . . ?
O3 C3 C4 113.61(11) . . ?
C2 C3 C4 101.21(10) . . ?
C30 C3 C4 113.74(9) . . ?
O4 C4 C5 108.66(10) . . ?
O4 C4 C3 111.21(10) . . ?
C5 C4 C3 103.96(10) . . ?
O4 C4 H4 110.9 . . ?
C5 C4 H4 110.9 . . ?
C3 C4 H4 110.9 . . ?
O1 C5 C4 106.45(11) . . ?
O1 C5 H5A 110.4 . . ?
C4 C5 H5A 110.4 . . ?
O1 C5 H5B 110.4 . . ?
C4 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?
C31 C30 C36 108.43(10) . . ?
C31 C30 C35 108.67(9) . . ?
C36 C30 C35 107.81(10) . . ?
C31 C30 C3 112.44(10) . . ?
C36 C30 C3 110.32(9) . . ?
C35 C30 C3 109.04(10) . . ?
C32 C31 C30 110.28(10) . . ?
C32 C31 H31A 109.6 . . ?
C30 C31 H31A 109.6 . . ?
C32 C31 H31B 109.6 . . ?
C30 C31 H31B 109.6 . . ?
H31A C31 H31B 108.1 . . ?
C38 C32 C33 109.32(10) . . ?
C38 C32 C31 109.82(10) . . ?
C33 C32 C31 109.68(10) . . ?
C38 C32 H32 109.3 . . ?
C33 C32 H32 109.3 . . ?
C31 C32 H32 109.3 . . ?
C34 C33 C32 109.45(10) . . ?
C34 C33 H33A 109.8 . . ?
C32 C33 H33A 109.8 . . ?
C34 C33 H33B 109.8 . . ?
C32 C33 H33B 109.8 . . ?
H33A C33 H33B 108.2 . . ?
C33 C34 C35 109.43(10) . . ?
C33 C34 C39 109.34(11) . . ?
C35 C34 C39 109.94(10) . . ?
C33 C34 H34 109.4 . . ?
C35 C34 H34 109.4 . . ?
C39 C34 H34 109.4 . . ?
C34 C35 C30 110.48(10) . . ?
C34 C35 H35A 109.6 . . ?
C30 C35 H35A 109.6 . . ?
C34 C35 H35B 109.6 . . ?
C30 C35 H35B 109.6 . . ?
H35A C35 H35B 108.1 . . ?
C37 C36 C30 110.76(9) . . ?
C37 C36 H36A 109.5 . . ?
C30 C36 H36A 109.5 . . ?
C37 C36 H36B 109.5 . . ?
C30 C36 H36B 109.5 . . ?
H36A C36 H36B 108.1 . . ?
C36 C37 C39 109.60(10) . . ?
C36 C37 C38 109.77(10) . . ?
C39 C37 C38 109.38(10) . . ?
C36 C37 H37 109.4 . . ?
C39 C37 H37 109.4 . . ?
C38 C37 H37 109.4 . . ?
C32 C38 C37 109.17(10) . . ?
C32 C38 H38A 109.8 . . ?
C37 C38 H38A 109.8 . . ?
C32 C38 H38B 109.8 . . ?
C37 C38 H38B 109.8 . . ?
H38A C38 H38B 108.3 . . ?
C37 C39 C34 109.07(10) . . ?
C37 C39 H39A 109.9 . . ?
C34 C39 H39A 109.9 . . ?
C37 C39 H39B 109.9 . . ?
C34 C39 H39B 109.9 . . ?
H39A C39 H39B 108.3 . . ?
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
O1 C2 1.3312(16) . ?
O1 C5 1.4595(16) . ?
O2 C2 1.2116(16) . ?
O3 C3 1.4066(16) . ?
O3 H3O 0.8401 . ?
O4 C4 1.4180(16) . ?
O4 H4O 0.8400 . ?
C2 C3 1.5402(17) . ?
C3 C30 1.5590(17) . ?
C3 C4 1.5628(17) . ?
C4 C5 1.520(2) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C30 C31 1.5429(17) . ?
C30 C36 1.5465(17) . ?
C30 C35 1.5472(17) . ?
C31 C32 1.5370(17) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C38 1.5323(17) . ?
C32 C33 1.5335(18) . ?
C32 H32 1.0000 . ?
C33 C34 1.5325(18) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.5343(17) . ?
C34 C39 1.5351(17) . ?
C34 H34 1.0000 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.5323(17) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C39 1.5325(18) . ?
C37 C38 1.5353(18) . ?
C37 H37 1.0000 . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
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
C5 O1 C2 O2 -176.03(11) . . . . ?
C5 O1 C2 C3 2.63(14) . . . . ?
O2 C2 C3 O3 41.76(17) . . . . ?
O1 C2 C3 O3 -136.80(11) . . . . ?
O2 C2 C3 C30 -76.37(16) . . . . ?
O1 C2 C3 C30 105.07(12) . . . . ?
O2 C2 C3 C4 162.41(12) . . . . ?
O1 C2 C3 C4 -16.15(13) . . . . ?
O3 C3 C4 O4 23.98(14) . . . . ?
C2 C3 C4 O4 -94.44(11) . . . . ?
C30 C3 C4 O4 146.02(10) . . . . ?
O3 C3 C4 C5 140.72(10) . . . . ?
C2 C3 C4 C5 22.31(12) . . . . ?
C30 C3 C4 C5 -97.23(12) . . . . ?
C2 O1 C5 C4 12.78(14) . . . . ?
O4 C4 C5 O1 96.43(12) . . . . ?
C3 C4 C5 O1 -22.09(12) . . . . ?
O3 C3 C30 C31 178.83(9) . . . . ?
C2 C3 C30 C31 -60.67(13) . . . . ?
C4 C3 C30 C31 52.92(14) . . . . ?
O3 C3 C30 C36 -60.00(12) . . . . ?
C2 C3 C30 C36 60.51(13) . . . . ?
C4 C3 C30 C36 174.10(10) . . . . ?
O3 C3 C30 C35 58.23(12) . . . . ?
C2 C3 C30 C35 178.73(9) . . . . ?
C4 C3 C30 C35 -67.68(13) . . . . ?
C36 C30 C31 C32 58.54(12) . . . . ?
C35 C30 C31 C32 -58.40(12) . . . . ?
C3 C30 C31 C32 -179.21(9) . . . . ?
C30 C31 C32 C38 -60.34(13) . . . . ?
C30 C31 C32 C33 59.81(12) . . . . ?
C38 C32 C33 C34 60.28(13) . . . . ?
C31 C32 C33 C34 -60.18(12) . . . . ?
C32 C33 C34 C35 60.16(12) . . . . ?
C32 C33 C34 C39 -60.31(13) . . . . ?
C33 C34 C35 C30 -59.96(12) . . . . ?
C39 C34 C35 C30 60.14(13) . . . . ?
C31 C30 C35 C34 58.65(12) . . . . ?
C36 C30 C35 C34 -58.68(12) . . . . ?
C3 C30 C35 C34 -178.46(9) . . . . ?
C31 C30 C36 C37 -58.41(13) . . . . ?
C35 C30 C36 C37 59.08(12) . . . . ?
C3 C30 C36 C37 178.05(10) . . . . ?
C30 C36 C37 C39 -60.58(13) . . . . ?
C30 C36 C37 C38 59.58(13) . . . . ?
C33 C32 C38 C37 -60.32(13) . . . . ?
C31 C32 C38 C37 60.06(13) . . . . ?
C36 C37 C38 C32 -59.60(13) . . . . ?
C39 C37 C38 C32 60.69(13) . . . . ?
C36 C37 C39 C34 59.75(13) . . . . ?
C38 C37 C39 C34 -60.65(13) . . . . ?
C33 C34 C39 C37 60.42(13) . . . . ?
C35 C34 C39 C37 -59.74(13) . . . . ?
