#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:11:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178424 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/45/4024559.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_4024559
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         'C17 H26 O4'
_chemical_formula_sum            'C17 H26 O4'
_chemical_formula_weight         294.38
_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                90.253(7)
_cell_angle_beta                 106.973(7)
_cell_angle_gamma                99.206(7)
_cell_formula_units_Z            4
_cell_length_a                   10.1757(14)
_cell_length_b                   12.1846(15)
_cell_length_c                   12.5108(17)
_cell_measurement_reflns_used    4659
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      29.5
_cell_measurement_theta_min      3.1
_cell_volume                     1462.4(3)
_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 0.796
_diffrn_measured_fraction_theta_max 0.796
_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  0.054
_diffrn_reflns_av_sigmaI/netI    0.045
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7254
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         3.1
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.32
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.19
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         4097
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.19
_refine_ls_R_factor_all          0.107
_refine_ls_R_factor_gt           0.093
_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)+(0.0922P)²+2.7442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.228
_refine_ls_wR_factor_ref         0.239
_reflns_number_gt                3476
_reflns_number_total             4097
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo900392y_si_003.cif
_cod_data_source_block           shelxl
_cod_database_code               4024559
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 0.2654(3) 0.3980(2) 0.1895(2) 0.0293(7) Uani 1 1 d . . .
O2 O 0.3784(3) 0.5379(3) 0.3263(3) 0.0337(7) Uani 1 1 d D . .
H2O H 0.3540 0.5828 0.2764 0.051 Uiso 1 1 d D . .
O3 O 0.2543(4) 0.2653(3) 0.3940(3) 0.0358(8) Uani 1 1 d . . .
O4 O 0.3580(3) 0.1829(2) 0.2871(2) 0.0265(7) Uani 1 1 d . . .
C2 C 0.2861(5) 0.4373(4) 0.2999(4) 0.0305(10) Uani 1 1 d . . .
H2 H 0.1952 0.4449 0.3124 0.037 Uiso 1 1 calc R . .
C3 C 0.3531(4) 0.3517(4) 0.3733(3) 0.0258(9) Uani 1 1 d . . .
H3 H 0.4205 0.3872 0.4448 0.031 Uiso 1 1 calc R . .
C4 C 0.4277(4) 0.2960(3) 0.3022(3) 0.0249(9) Uani 1 1 d . . .
C5 C 0.3863(4) 0.3529(4) 0.1913(3) 0.0282(9) Uani 1 1 d . . .
H5A H 0.4625 0.4126 0.1868 0.034 Uiso 1 1 calc R . .
H5B H 0.3659 0.2982 0.1274 0.034 Uiso 1 1 calc R . .
C6 C 0.2381(5) 0.1693(4) 0.3249(4) 0.0335(11) Uani 1 1 d . . .
C40 C 0.5849(4) 0.2982(3) 0.3522(3) 0.0236(9) Uani 1 1 d . . .
C41 C 0.6141(5) 0.2305(4) 0.4566(3) 0.0285(10) Uani 1 1 d . . .
H41A H 0.5785 0.2626 0.5132 0.034 Uiso 1 1 calc R . .
H41B H 0.5647 0.1529 0.4369 0.034 Uiso 1 1 calc R . .
C42 C 0.7692(5) 0.2306(4) 0.5053(4) 0.0288(10) Uani 1 1 d . . .
H42 H 0.7864 0.1864 0.5737 0.035 Uiso 1 1 calc R . .
C43 C 0.8462(5) 0.3497(4) 0.5356(4) 0.0348(10) Uani 1 1 d . . .
H43A H 0.8136 0.3839 0.5930 0.042 Uiso 1 1 calc R . .
H43B H 0.9475 0.3496 0.5672 0.042 Uiso 1 1 calc R . .
C44 C 0.8198(5) 0.4164(4) 0.4328(4) 0.0341(10) Uani 1 1 d . . .
H44 H 0.8702 0.4946 0.4531 0.041 Uiso 1 1 calc R . .
C46 C 0.6407(5) 0.2454(4) 0.2663(3) 0.0302(10) Uani 1 1 d . . .
H46A H 0.5917 0.1678 0.2461 0.036 Uiso 1 1 calc R . .
H46B H 0.6228 0.2875 0.1975 0.036 Uiso 1 1 calc R . .
C45 C 0.6635(4) 0.4169(3) 0.3847(4) 0.0283(9) Uani 1 1 d . . .
H45A H 0.6291 0.4511 0.4410 0.034 Uiso 1 1 calc R . .
H45B H 0.6463 0.4621 0.3180 0.034 Uiso 1 1 calc R . .
C47 C 0.7963(5) 0.2463(4) 0.3146(4) 0.0329(10) Uani 1 1 d . . .
H47 H 0.8315 0.2124 0.2577 0.040 Uiso 1 1 calc R . .
C48 C 0.8228(5) 0.1789(4) 0.4184(4) 0.0356(10) Uani 1 1 d . . .
H48A H 0.9239 0.1781 0.4497 0.043 Uiso 1 1 calc R . .
H48B H 0.7745 0.1011 0.3984 0.043 Uiso 1 1 calc R . .
C49 C 0.8736(5) 0.3638(4) 0.3467(4) 0.0384(11) Uani 1 1 d . . .
H49A H 0.8597 0.4083 0.2795 0.046 Uiso 1 1 calc R . .
H49B H 0.9746 0.3630 0.3785 0.046 Uiso 1 1 calc R . .
C61 C 0.1083(5) 0.1589(5) 0.2278(5) 0.0479(13) Uani 1 1 d . . .
H61A H 0.0998 0.0916 0.1814 0.072 Uiso 1 1 calc R . .
H61B H 0.1132 0.2243 0.1830 0.072 Uiso 1 1 calc R . .
H61C H 0.0270 0.1540 0.2556 0.072 Uiso 1 1 calc R . .
C62 C 0.2384(7) 0.0693(4) 0.3956(5) 0.0487(14) Uani 1 1 d . . .
H62A H 0.2272 0.0018 0.3487 0.073 Uiso 1 1 calc R . .
H62B H 0.1612 0.0639 0.4284 0.073 Uiso 1 1 calc R . .
H62C H 0.3269 0.0773 0.4555 0.073 Uiso 1 1 calc R . .
O1A O 0.7394(3) 0.1069(2) 0.8046(2) 0.0290(7) Uani 1 1 d . . .
O2A O 0.6253(3) -0.0349(3) 0.8856(3) 0.0334(7) Uani 1 1 d D . .
H2AO H 0.6430 -0.0725 0.8367 0.050 Uiso 1 1 d D . .
O3A O 0.7445(3) 0.2376(3) 1.0155(2) 0.0293(7) Uani 1 1 d . . .
O4A O 0.6444(3) 0.3205(2) 0.8579(2) 0.0264(7) Uani 1 1 d . . .
C2A C 0.7175(4) 0.0666(4) 0.9041(4) 0.0290(9) Uani 1 1 d . . .
H2A H 0.8081 0.0595 0.9603 0.035 Uiso 1 1 calc R . .
C3A C 0.6477(4) 0.1522(3) 0.9464(3) 0.0246(9) Uani 1 1 d . . .
H3A H 0.5794 0.1159 0.9843 0.030 Uiso 1 1 calc R . .
C4A C 0.5745(4) 0.2066(3) 0.8395(3) 0.0238(9) Uani 1 1 d . . .
C5A C 0.6184(4) 0.1507(4) 0.7490(3) 0.0269(9) Uani 1 1 d . . .
H5A1 H 0.5432 0.0904 0.7074 0.032 Uiso 1 1 calc R . .
H5A2 H 0.6386 0.2056 0.6954 0.032 Uiso 1 1 calc R . .
C6A C 0.7610(5) 0.3351(4) 0.9558(3) 0.0294(10) Uani 1 1 d . . .
C40A C 0.4168(4) 0.2043(3) 0.8144(3) 0.0246(9) Uani 1 1 d . . .
C41A C 0.3607(5) 0.2569(4) 0.7035(3) 0.0293(10) Uani 1 1 d . . .
H41C H 0.4094 0.3346 0.7073 0.035 Uiso 1 1 calc R . .
H41D H 0.3784 0.2150 0.6426 0.035 Uiso 1 1 calc R . .
C42A C 0.2050(5) 0.2555(4) 0.6788(4) 0.0315(10) Uani 1 1 d . . .
H42A H 0.1694 0.2899 0.6058 0.038 Uiso 1 1 calc R . .
C43A C 0.1296(5) 0.1361(4) 0.6714(4) 0.0371(11) Uani 1 1 d . . .
H43C H 0.0281 0.1352 0.6545 0.044 Uiso 1 1 calc R . .
H43D H 0.1455 0.0931 0.6104 0.044 Uiso 1 1 calc R . .
C44A C 0.1831(5) 0.0836(4) 0.7810(4) 0.0340(10) Uani 1 1 d . . .
H44A H 0.1340 0.0050 0.7755 0.041 Uiso 1 1 calc R . .
C45A C 0.3393(5) 0.0844(4) 0.8063(4) 0.0302(10) Uani 1 1 d . . .
H45C H 0.3568 0.0410 0.7463 0.036 Uiso 1 1 calc R . .
H45D H 0.3743 0.0490 0.8779 0.036 Uiso 1 1 calc R . .
C46A C 0.3864(4) 0.2684(4) 0.9071(3) 0.0274(9) Uani 1 1 d . . .
H46C H 0.4214 0.2341 0.9793 0.033 Uiso 1 1 calc R . .
H46D H 0.4356 0.3463 0.9141 0.033 Uiso 1 1 calc R . .
C47A C 0.2310(5) 0.2673(4) 0.8816(4) 0.0281(10) Uani 1 1 d . . .
H47A H 0.2135 0.3103 0.9429 0.034 Uiso 1 1 calc R . .
C48A C 0.1777(4) 0.3218(4) 0.7709(4) 0.0301(10) Uani 1 1 d . . .
H48C H 0.0766 0.3225 0.7541 0.036 Uiso 1 1 calc R . .
H48D H 0.2264 0.3996 0.7760 0.036 Uiso 1 1 calc R . .
C49A C 0.1554(5) 0.1477(4) 0.8740(4) 0.0346(11) Uani 1 1 d . . .
H49C H 0.1893 0.1127 0.9460 0.041 Uiso 1 1 calc R . .
H49D H 0.0540 0.1466 0.8580 0.041 Uiso 1 1 calc R . .
C61A C 0.8939(5) 0.3487(4) 0.9232(4) 0.0393(11) Uani 1 1 d . . .
H61D H 0.9021 0.4166 0.8822 0.059 Uiso 1 1 calc R . .
H61E H 0.8922 0.2842 0.8754 0.059 Uiso 1 1 calc R . .
H61F H 0.9738 0.3542 0.9907 0.059 Uiso 1 1 calc R . .
C62A C 0.7532(5) 0.4332(4) 1.0253(4) 0.0372(11) Uani 1 1 d . . .
H62D H 0.7645 0.5011 0.9850 0.056 Uiso 1 1 calc R . .
H62E H 0.8276 0.4397 1.0966 0.056 Uiso 1 1 calc R . .
H62F H 0.6625 0.4227 1.0396 0.056 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 105.8(3) . . ?
C2 O2 H2O 109.7 . . ?
C6 O3 C3 111.0(3) . . ?
C6 O4 C4 111.7(3) . . ?
O2 C2 O1 111.5(3) . . ?
O2 C2 C3 107.6(4) . . ?
O1 C2 C3 105.6(4) . . ?
O2 C2 H2 110.7 . . ?
O1 C2 H2 110.7 . . ?
C3 C2 H2 110.7 . . ?
O3 C3 C2 112.7(4) . . ?
O3 C3 C4 105.4(3) . . ?
C2 C3 C4 104.5(3) . . ?
O3 C3 H3 111.3 . . ?
C2 C3 H3 111.3 . . ?
C4 C3 H3 111.3 . . ?
O4 C4 C5 109.4(3) . . ?
O4 C4 C40 109.0(3) . . ?
C5 C4 C40 114.5(3) . . ?
O4 C4 C3 103.3(3) . . ?
C5 C4 C3 102.5(3) . . ?
C40 C4 C3 117.4(3) . . ?
O1 C5 C4 106.2(3) . . ?
O1 C5 H5A 110.5 . . ?
C4 C5 H5A 110.5 . . ?
O1 C5 H5B 110.5 . . ?
C4 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
O3 C6 O4 105.4(3) . . ?
O3 C6 C61 111.3(4) . . ?
O4 C6 C61 110.6(4) . . ?
O3 C6 C62 108.4(4) . . ?
O4 C6 C62 109.0(4) . . ?
C61 C6 C62 112.0(4) . . ?
C45 C40 C41 108.4(3) . . ?
C45 C40 C4 111.5(3) . . ?
C41 C40 C4 110.4(3) . . ?
C45 C40 C46 109.2(3) . . ?
C41 C40 C46 107.9(3) . . ?
C4 C40 C46 109.4(3) . . ?
C42 C41 C40 110.7(3) . . ?
C42 C41 H41A 109.5 . . ?
C40 C41 H41A 109.5 . . ?
C42 C41 H41B 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 108.1 . . ?
C41 C42 C43 109.9(4) . . ?
C41 C42 C48 109.2(4) . . ?
C43 C42 C48 108.8(4) . . ?
C41 C42 H42 109.6 . . ?
C43 C42 H42 109.6 . . ?
C48 C42 H42 109.6 . . ?
C44 C43 C42 109.7(4) . . ?
C44 C43 H43A 109.7 . . ?
C42 C43 H43A 109.7 . . ?
C44 C43 H43B 109.7 . . ?
C42 C43 H43B 109.7 . . ?
H43A C43 H43B 108.2 . . ?
C43 C44 C49 108.8(4) . . ?
C43 C44 C45 109.6(4) . . ?
C49 C44 C45 110.0(4) . . ?
C43 C44 H44 109.5 . . ?
C49 C44 H44 109.5 . . ?
C45 C44 H44 109.5 . . ?
C47 C46 C40 110.1(3) . . ?
C47 C46 H46A 109.6 . . ?
C40 C46 H46A 109.6 . . ?
C47 C46 H46B 109.6 . . ?
C40 C46 H46B 109.6 . . ?
H46A C46 H46B 108.2 . . ?
C40 C45 C44 110.2(4) . . ?
C40 C45 H45A 109.6 . . ?
C44 C45 H45A 109.6 . . ?
C40 C45 H45B 109.6 . . ?
C44 C45 H45B 109.6 . . ?
H45A C45 H45B 108.1 . . ?
C49 C47 C46 110.7(4) . . ?
C49 C47 C48 108.8(4) . . ?
C46 C47 C48 109.4(4) . . ?
C49 C47 H47 109.3 . . ?
C46 C47 H47 109.3 . . ?
C48 C47 H47 109.3 . . ?
C47 C48 C42 109.4(4) . . ?
C47 C48 H48A 109.8 . . ?
C42 C48 H48A 109.8 . . ?
C47 C48 H48B 109.8 . . ?
C42 C48 H48B 109.8 . . ?
H48A C48 H48B 108.2 . . ?
C47 C49 C44 109.7(4) . . ?
C47 C49 H49A 109.7 . . ?
C44 C49 H49A 109.7 . . ?
C47 C49 H49B 109.7 . . ?
C44 C49 H49B 109.7 . . ?
H49A C49 H49B 108.2 . . ?
C6 C61 H61A 109.5 . . ?
C6 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
C6 C61 H61C 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
C6 C62 H62A 109.5 . . ?
C6 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
C6 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
C2A O1A C5A 105.6(3) . . ?
C2A O2A H2AO 107.2 . . ?
C3A O3A C6A 111.0(3) . . ?
C6A O4A C4A 111.4(3) . . ?
O2A C2A O1A 112.2(3) . . ?
O2A C2A C3A 107.1(3) . . ?
O1A C2A C3A 105.6(3) . . ?
O2A C2A H2A 110.6 . . ?
O1A C2A H2A 110.6 . . ?
C3A C2A H2A 110.6 . . ?
O3A C3A C2A 112.5(3) . . ?
O3A C3A C4A 106.2(3) . . ?
C2A C3A C4A 103.7(3) . . ?
O3A C3A H3A 111.3 . . ?
C2A C3A H3A 111.3 . . ?
C4A C3A H3A 111.3 . . ?
O4A C4A C5A 108.5(3) . . ?
O4A C4A C40A 108.9(3) . . ?
C5A C4A C40A 115.4(3) . . ?
O4A C4A C3A 103.3(3) . . ?
C5A C4A C3A 103.0(3) . . ?
C40A C4A C3A 116.9(3) . . ?
O1A C5A C4A 106.5(3) . . ?
O1A C5A H5A1 110.4 . . ?
C4A C5A H5A1 110.4 . . ?
O1A C5A H5A2 110.4 . . ?
C4A C5A H5A2 110.4 . . ?
H5A1 C5A H5A2 108.6 . . ?
O3A C6A O4A 105.6(3) . . ?
O3A C6A C62A 108.6(3) . . ?
O4A C6A C62A 108.5(4) . . ?
O3A C6A C61A 111.6(4) . . ?
O4A C6A C61A 109.7(4) . . ?
C62A C6A C61A 112.7(4) . . ?
C41A C40A C46A 109.1(4) . . ?
C41A C40A C45A 108.5(3) . . ?
C46A C40A C45A 108.0(3) . . ?
C41A C40A C4A 109.8(3) . . ?
C46A C40A C4A 110.6(3) . . ?
C45A C40A C4A 110.8(3) . . ?
C42A C41A C40A 110.0(3) . . ?
C42A C41A H41C 109.7 . . ?
C40A C41A H41C 109.7 . . ?
C42A C41A H41D 109.7 . . ?
C40A C41A H41D 109.7 . . ?
H41C C41A H41D 108.2 . . ?
C48A C42A C41A 109.8(4) . . ?
C48A C42A C43A 109.6(4) . . ?
C41A C42A C43A 109.8(4) . . ?
C48A C42A H42A 109.2 . . ?
C41A C42A H42A 109.2 . . ?
C43A C42A H42A 109.2 . . ?
C44A C43A C42A 109.5(4) . . ?
C44A C43A H43C 109.8 . . ?
C42A C43A H43C 109.8 . . ?
C44A C43A H43D 109.8 . . ?
C42A C43A H43D 109.8 . . ?
H43C C43A H43D 108.2 . . ?
C43A C44A C49A 109.8(4) . . ?
C43A C44A C45A 109.6(4) . . ?
C49A C44A C45A 109.9(4) . . ?
C43A C44A H44A 109.2 . . ?
C49A C44A H44A 109.2 . . ?
C45A C44A H44A 109.2 . . ?
C44A C45A C40A 110.1(4) . . ?
C44A C45A H45C 109.6 . . ?
C40A C45A H45C 109.6 . . ?
C44A C45A H45D 109.6 . . ?
C40A C45A H45D 109.6 . . ?
H45C C45A H45D 108.2 . . ?
C47A C46A C40A 110.6(3) . . ?
C47A C46A H46C 109.5 . . ?
C40A C46A H46C 109.5 . . ?
C47A C46A H46D 109.5 . . ?
C40A C46A H46D 109.5 . . ?
H46C C46A H46D 108.1 . . ?
C46A C47A C49A 109.6(4) . . ?
C46A C47A C48A 109.4(3) . . ?
C49A C47A C48A 110.0(4) . . ?
C46A C47A H47A 109.3 . . ?
C49A C47A H47A 109.3 . . ?
C48A C47A H47A 109.3 . . ?
C42A C48A C47A 108.5(4) . . ?
C42A C48A H48C 110.0 . . ?
C47A C48A H48C 110.0 . . ?
C42A C48A H48D 110.0 . . ?
C47A C48A H48D 110.0 . . ?
H48C C48A H48D 108.4 . . ?
C44A C49A C47A 108.7(3) . . ?
C44A C49A H49C 110.0 . . ?
C47A C49A H49C 110.0 . . ?
C44A C49A H49D 110.0 . . ?
C47A C49A H49D 110.0 . . ?
H49C C49A H49D 108.3 . . ?
C6A C61A H61D 109.5 . . ?
C6A C61A H61E 109.5 . . ?
H61D C61A H61E 109.5 . . ?
C6A C61A H61F 109.5 . . ?
H61D C61A H61F 109.5 . . ?
H61E C61A H61F 109.5 . . ?
C6A C62A H62D 109.5 . . ?
C6A C62A H62E 109.5 . . ?
H62D C62A H62E 109.5 . . ?
C6A C62A H62F 109.5 . . ?
H62D C62A H62F 109.5 . . ?
H62E C62A H62F 109.5 . . ?
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 1.405(5) . ?
O1 C5 1.420(5) . ?
O2 C2 1.394(5) . ?
O2 H2O 0.8400 . ?
O3 C6 1.409(6) . ?
O3 C3 1.415(5) . ?
O4 C6 1.419(5) . ?
O4 C4 1.430(5) . ?
C2 C3 1.505(6) . ?
C2 H2 1.0000 . ?
C3 C4 1.544(6) . ?
C3 H3 1.0000 . ?
C4 C5 1.530(6) . ?
C4 C40 1.534(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C61 1.498(7) . ?
C6 C62 1.508(7) . ?
C40 C45 1.527(6) . ?
C40 C41 1.529(6) . ?
C40 C46 1.536(6) . ?
C41 C42 1.516(6) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 C43 1.524(7) . ?
C42 C48 1.525(7) . ?
C42 H42 1.0000 . ?
C43 C44 1.505(7) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C49 1.523(7) . ?
C44 C45 1.529(6) . ?
C44 H44 1.0000 . ?
C46 C47 1.519(6) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C47 C49 1.510(7) . ?
C47 C48 1.519(6) . ?
C47 H47 1.0000 . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C61 H61A 0.9800 . ?
C61 H61B 0.9800 . ?
C61 H61C 0.9800 . ?
C62 H62A 0.9800 . ?
C62 H62B 0.9800 . ?
C62 H62C 0.9800 . ?
O1A C2A 1.404(5) . ?
O1A C5A 1.414(5) . ?
O2A C2A 1.401(5) . ?
O2A H2AO 0.8400 . ?
O3A C3A 1.403(5) . ?
O3A C6A 1.419(5) . ?
O4A C6A 1.423(5) . ?
O4A C4A 1.439(5) . ?
C2A C3A 1.524(6) . ?
C2A H2A 1.0000 . ?
C3A C4A 1.539(6) . ?
C3A H3A 1.0000 . ?
C4A C5A 1.527(6) . ?
C4A C40A 1.538(6) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A C62A 1.500(7) . ?
C6A C61A 1.508(6) . ?
C40A C41A 1.524(6) . ?
C40A C46A 1.526(6) . ?
C40A C45A 1.533(6) . ?
C41A C42A 1.520(6) . ?
C41A H41C 0.9900 . ?
C41A H41D 0.9900 . ?
C42A C48A 1.519(6) . ?
C42A C43A 1.521(7) . ?
C42A H42A 1.0000 . ?
C43A C44A 1.506(7) . ?
C43A H43C 0.9900 . ?
C43A H43D 0.9900 . ?
C44A C49A 1.515(7) . ?
C44A C45A 1.525(6) . ?
C44A H44A 1.0000 . ?
C45A H45C 0.9900 . ?
C45A H45D 0.9900 . ?
C46A C47A 1.517(6) . ?
C46A H46C 0.9900 . ?
C46A H46D 0.9900 . ?
C47A C49A 1.525(6) . ?
C47A C48A 1.528(6) . ?
C47A H47A 1.0000 . ?
C48A H48C 0.9900 . ?
C48A H48D 0.9900 . ?
C49A H49C 0.9900 . ?
C49A H49D 0.9900 . ?
C61A H61D 0.9800 . ?
C61A H61E 0.9800 . ?
C61A H61F 0.9800 . ?
C62A H62D 0.9800 . ?
C62A H62E 0.9800 . ?
C62A H62F 0.9800 . ?
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 76.8(4) . . . . ?
C5 O1 C2 C3 -39.7(4) . . . . ?
C6 O3 C3 C2 100.6(4) . . . . ?
C6 O3 C3 C4 -12.8(5) . . . . ?
O2 C2 C3 O3 152.6(3) . . . . ?
O1 C2 C3 O3 -88.2(4) . . . . ?
O2 C2 C3 C4 -93.5(4) . . . . ?
O1 C2 C3 C4 25.7(4) . . . . ?
C6 O4 C4 C5 -99.2(4) . . . . ?
C6 O4 C4 C40 134.9(4) . . . . ?
C6 O4 C4 C3 9.4(4) . . . . ?
O3 C3 C4 O4 2.0(4) . . . . ?
C2 C3 C4 O4 -117.0(3) . . . . ?
O3 C3 C4 C5 115.7(4) . . . . ?
C2 C3 C4 C5 -3.3(4) . . . . ?
O3 C3 C4 C40 -117.9(4) . . . . ?
C2 C3 C4 C40 123.1(4) . . . . ?
C2 O1 C5 C4 37.6(4) . . . . ?
O4 C4 C5 O1 89.2(4) . . . . ?
C40 C4 C5 O1 -148.1(3) . . . . ?
C3 C4 C5 O1 -19.9(4) . . . . ?
C3 O3 C6 O4 18.5(5) . . . . ?
C3 O3 C6 C61 -101.4(4) . . . . ?
C3 O3 C6 C62 135.0(4) . . . . ?
C4 O4 C6 O3 -17.2(5) . . . . ?
C4 O4 C6 C61 103.2(4) . . . . ?
C4 O4 C6 C62 -133.3(4) . . . . ?
O4 C4 C40 C45 -172.5(3) . . . . ?
C5 C4 C40 C45 64.6(4) . . . . ?
C3 C4 C40 C45 -55.6(4) . . . . ?
O4 C4 C40 C41 -52.0(4) . . . . ?
C5 C4 C40 C41 -174.8(4) . . . . ?
C3 C4 C40 C41 64.9(5) . . . . ?
O4 C4 C40 C46 66.6(4) . . . . ?
C5 C4 C40 C46 -56.3(5) . . . . ?
C3 C4 C40 C46 -176.5(3) . . . . ?
C45 C40 C41 C42 -58.6(5) . . . . ?
C4 C40 C41 C42 179.0(3) . . . . ?
C46 C40 C41 C42 59.5(5) . . . . ?
C40 C41 C42 C43 59.1(5) . . . . ?
C40 C41 C42 C48 -60.3(5) . . . . ?
C41 C42 C43 C44 -59.2(5) . . . . ?
C48 C42 C43 C44 60.3(5) . . . . ?
C42 C43 C44 C49 -60.6(5) . . . . ?
C42 C43 C44 C45 59.7(5) . . . . ?
C45 C40 C46 C47 58.0(4) . . . . ?
C41 C40 C46 C47 -59.6(4) . . . . ?
C4 C40 C46 C47 -179.7(3) . . . . ?
C41 C40 C45 C44 59.0(4) . . . . ?
C4 C40 C45 C44 -179.3(3) . . . . ?
C46 C40 C45 C44 -58.3(4) . . . . ?
C43 C44 C45 C40 -60.5(5) . . . . ?
C49 C44 C45 C40 59.2(5) . . . . ?
C40 C46 C47 C49 -59.0(5) . . . . ?
C40 C46 C47 C48 60.8(5) . . . . ?
C49 C47 C48 C42 60.7(5) . . . . ?
C46 C47 C48 C42 -60.3(5) . . . . ?
C41 C42 C48 C47 59.8(5) . . . . ?
C43 C42 C48 C47 -60.1(5) . . . . ?
C46 C47 C49 C44 59.1(5) . . . . ?
C48 C47 C49 C44 -61.1(5) . . . . ?
C43 C44 C49 C47 61.2(5) . . . . ?
C45 C44 C49 C47 -58.9(5) . . . . ?
C5A O1A C2A O2A 76.4(4) . . . . ?
C5A O1A C2A C3A -40.0(4) . . . . ?
C6A O3A C3A C2A 100.9(4) . . . . ?
C6A O3A C3A C4A -11.9(4) . . . . ?
O2A C2A C3A O3A 151.8(3) . . . . ?
O1A C2A C3A O3A -88.4(4) . . . . ?
O2A C2A C3A C4A -93.8(4) . . . . ?
O1A C2A C3A C4A 25.9(4) . . . . ?
C6A O4A C4A C5A -101.2(4) . . . . ?
C6A O4A C4A C40A 132.5(3) . . . . ?
C6A O4A C4A C3A 7.6(4) . . . . ?
O3A C3A C4A O4A 2.5(4) . . . . ?
C2A C3A C4A O4A -116.3(3) . . . . ?
O3A C3A C4A C5A 115.4(3) . . . . ?
C2A C3A C4A C5A -3.4(4) . . . . ?
O3A C3A C4A C40A -117.0(4) . . . . ?
C2A C3A C4A C40A 124.2(4) . . . . ?
C2A O1A C5A C4A 37.9(4) . . . . ?
O4A C4A C5A O1A 89.0(4) . . . . ?
C40A C4A C5A O1A -148.6(3) . . . . ?
C3A C4A C5A O1A -20.1(4) . . . . ?
C3A O3A C6A O4A 16.5(4) . . . . ?
C3A O3A C6A C62A 132.7(4) . . . . ?
C3A O3A C6A C61A -102.5(4) . . . . ?
C4A O4A C6A O3A -14.8(4) . . . . ?
C4A O4A C6A C62A -131.1(4) . . . . ?
C4A O4A C6A C61A 105.5(4) . . . . ?
O4A C4A C40A C41A 66.0(4) . . . . ?
C5A C4A C40A C41A -56.2(5) . . . . ?
C3A C4A C40A C41A -177.5(3) . . . . ?
O4A C4A C40A C46A -54.4(4) . . . . ?
C5A C4A C40A C46A -176.6(3) . . . . ?
C3A C4A C40A C46A 62.1(5) . . . . ?
O4A C4A C40A C45A -174.1(3) . . . . ?
C5A C4A C40A C45A 63.7(4) . . . . ?
C3A C4A C40A C45A -57.6(5) . . . . ?
C46A C40A C41A C42A -58.3(5) . . . . ?
C45A C40A C41A C42A 59.1(5) . . . . ?
C4A C40A C41A C42A -179.6(3) . . . . ?
C40A C41A C42A C48A 60.5(5) . . . . ?
C40A C41A C42A C43A -60.0(5) . . . . ?
C48A C42A C43A C44A -60.6(5) . . . . ?
C41A C42A C43A C44A 60.1(5) . . . . ?
C42A C43A C44A C49A 60.9(5) . . . . ?
C42A C43A C44A C45A -59.9(5) . . . . ?
C43A C44A C45A C40A 60.1(5) . . . . ?
C49A C44A C45A C40A -60.6(5) . . . . ?
C41A C40A C45A C44A -59.2(5) . . . . ?
C46A C40A C45A C44A 59.0(4) . . . . ?
C4A C40A C45A C44A -179.8(3) . . . . ?
C41A C40A C46A C47A 58.5(4) . . . . ?
C45A C40A C46A C47A -59.3(4) . . . . ?
C4A C40A C46A C47A 179.3(3) . . . . ?
C40A C46A C47A C49A 60.8(4) . . . . ?
C40A C46A C47A C48A -60.0(5) . . . . ?
C41A C42A C48A C47A -61.0(4) . . . . ?
C43A C42A C48A C47A 59.7(4) . . . . ?
C46A C47A C48A C42A 60.5(5) . . . . ?
C49A C47A C48A C42A -60.0(4) . . . . ?
C43A C44A C49A C47A -60.4(5) . . . . ?
C45A C44A C49A C47A 60.2(5) . . . . ?
C46A C47A C49A C44A -60.1(5) . . . . ?
C48A C47A C49A C44A 60.2(5) . . . . ?
