#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:20:57 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178466 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/87/4028712.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_4028712
loop_
_publ_author_name
'Dominik Hager'
'Christian Paulitz'
'Jörg Tiebes'
'Peter Mayer'
'Dirk Trauner'
_publ_section_title
;
 Total Synthesis of Herbicidin C and Aureonuclemycin: Impasses and New
 Avenues
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10784
_journal_page_last               10801
_journal_paper_doi               10.1021/jo401706r
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C10 H14 O5'
_chemical_formula_sum            'C10 H14 O5'
_chemical_formula_weight         214.215
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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
_audit_block_code                C10H14O5_ex262_trauner
_audit_creation_date
;
'Sat May 30 21:33:44 2009'
;
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             26-Jul-12
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1089(3)
_cell_length_b                   7.2805(3)
_cell_length_c                   20.2476(8)
_cell_measurement_reflns_used    5396
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      32.6578
_cell_measurement_theta_min      4.1152
_cell_volume                     1047.94(7)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
;
_computing_structure_refinement
;
Sheldrick, G. M. (2008).
Acta Cryst. A64, 112--122.
;
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details
;
1 omega 0.00 101.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 30.0000 70.0000 0.0000 101

2 omega 0.00 101.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 30.0000 70.0000 120.0000 101

3 omega 0.00 101.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 30.0000 70.0000 240.0000 101

4 omega -41.00 60.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 30.0000 -70.0000 0.0000 101

5 omega -41.00 60.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 30.0000 -70.0000 120.0000 101

6 omega -41.00 60.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 30.0000 -70.0000 240.0000 101

;
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Oxford XCalibur'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0936900351
_diffrn_orient_matrix_UB_12      0.0330689735
_diffrn_orient_matrix_UB_13      -0.0025873196
_diffrn_orient_matrix_UB_21      -0.0078787940
_diffrn_orient_matrix_UB_22      -0.0000777632
_diffrn_orient_matrix_UB_23      0.0349637557
_diffrn_orient_matrix_UB_31      0.0336510123
_diffrn_orient_matrix_UB_32      0.0917660242
_diffrn_orient_matrix_UB_33      0.0009460359
_diffrn_radiation_collimation    '0.5 mm collimator'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15607
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         32.73
_diffrn_reflns_theta_min         4.13
_diffrn_source_current           40_mA
_diffrn_source_power             2.00_kW
_diffrn_source_type              'Spellman generator'
_diffrn_source_voltage           50_kV
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May 6 2009,17:20:42)
empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.35778(9)
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.878
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         3595
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.878
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0339
_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)+(0.0381P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0717
_reflns_number_gt                2560
_reflns_number_total             3595
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401706r_si_002_7.cif
_cod_data_source_block           ex262
_cod_database_code               4028712
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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
O2 O 0.42336(10) 0.17327(10) 0.32432(4) 0.03653(19) Uani 1 1 d .
O3 O 0.09227(11) 0.05454(9) 0.40543(4) 0.03176(18) Uani 1 1 d .
O5 O 0.06416(12) 0.49102(10) 0.37079(4) 0.03616(19) Uani 1 1 d .
O4 O -0.06942(11) 0.30610(10) 0.44672(4) 0.03482(18) Uani 1 1 d .
O1 O 0.64221(12) -0.03229(13) 0.30984(5) 0.0490(2) Uani 1 1 d .
C1 C 0.47647(16) -0.00355(17) 0.31627(6) 0.0338(3) Uani 1 1 d .
C4 C 0.08634(14) 0.08481(14) 0.33502(5) 0.0274(2) Uani 1 1 d .
H4 H -0.0415 0.1282 0.3216 0.033 Uiso 1 1 calc R
C8 C -0.06659(16) 0.49167(15) 0.42476(5) 0.0321(2) Uani 1 1 d .
C5 C 0.22938(13) 0.23544(14) 0.32438(6) 0.0283(2) Uani 1 1 d .
H5 H 0.2007 0.3057 0.2832 0.034 Uiso 1 1 calc R
C7 C 0.11018(15) 0.22706(15) 0.43552(5) 0.0310(2) Uani 1 1 d .
H7 H 0.1853 0.2197 0.4772 0.037 Uiso 1 1 calc R
C3 C 0.13413(16) -0.09086(17) 0.29965(6) 0.0347(3) Uani 1 1 d .
H3A H 0.1255 -0.0716 0.2513 0.042 Uiso 1 1 calc R
H3B H 0.0430 -0.1877 0.3121 0.042 Uiso 1 1 calc R
C6 C 0.20310(15) 0.35560(15) 0.38473(6) 0.0309(2) Uani 1 1 d .
H6 H 0.3238 0.4097 0.4010 0.037 Uiso 1 1 calc R
C10 C 0.0003(2) 0.61706(19) 0.47923(7) 0.0512(4) Uani 1 1 d .
H10A H -0.0864 0.6092 0.5168 0.077 Uiso 1 1 calc R
H10B H 0.0043 0.7438 0.4630 0.077 Uiso 1 1 calc R
H10C H 0.1265 0.5796 0.4933 0.077 Uiso 1 1 calc R
C9 C -0.25743(17) 0.5407(2) 0.39840(7) 0.0468(3) Uani 1 1 d .
H9A H -0.2978 0.4472 0.3666 0.070 Uiso 1 1 calc R
H9B H -0.2514 0.6605 0.3765 0.070 Uiso 1 1 calc R
H9C H -0.3477 0.5463 0.4349 0.070 Uiso 1 1 calc R
C2 C 0.33198(16) -0.15196(16) 0.31767(6) 0.0373(3) Uani 1 1 d .
H2A H 0.3292 -0.2058 0.3626 0.045 Uiso 1 1 calc R
H2B H 0.3709 -0.2501 0.2867 0.045 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
C1 O2 C5 124.24(8)
C7 O3 C4 107.17(8)
C6 O5 C8 107.50(8)
C7 O4 C8 108.82(8)
O1 C1 O2 116.88(12)
O1 C1 C2 123.40(12)
O2 C1 C2 119.70(9)
O3 C4 C3 109.50(8)
O3 C4 C5 103.41(8)
C3 C4 C5 113.40(9)
O3 C4 H4 110.1
C3 C4 H4 110.1
C5 C4 H4 110.1
O4 C8 O5 104.13(8)
O4 C8 C9 108.91(10)
O5 C8 C9 108.40(9)
O4 C8 C10 110.52(10)
O5 C8 C10 110.77(10)
C9 C8 C10 113.64(11)
O2 C5 C4 114.40(8)
O2 C5 C6 107.34(8)
C4 C5 C6 102.78(8)
O2 C5 H5 110.7
C4 C5 H5 110.7
C6 C5 H5 110.7
O3 C7 O4 110.56(9)
O3 C7 C6 107.06(8)
O4 C7 C6 104.26(8)
O3 C7 H7 111.5
O4 C7 H7 111.5
C6 C7 H7 111.5
C4 C3 C2 110.09(9)
C4 C3 H3A 109.6
C2 C3 H3A 109.6
C4 C3 H3B 109.6
C2 C3 H3B 109.6
H3A C3 H3B 108.2
O5 C6 C5 109.01(8)
O5 C6 C7 104.82(8)
C5 C6 C7 103.93(8)
O5 C6 H6 112.8
C5 C6 H6 112.8
C7 C6 H6 112.8
C8 C10 H10A 109.5
C8 C10 H10B 109.5
H10A C10 H10B 109.5
C8 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C8 C9 H9A 109.5
C8 C9 H9B 109.5
H9A C9 H9B 109.5
C8 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C1 C2 C3 114.89(9)
C1 C2 H2A 108.5
C3 C2 H2A 108.5
C1 C2 H2B 108.5
C3 C2 H2B 108.5
H2A C2 H2B 107.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C1 1.3514(14)
O2 C5 1.4514(11)
O3 C7 1.4018(13)
O3 C4 1.4433(12)
O5 C6 1.4238(13)
O5 C8 1.4346(13)
O4 C7 1.4188(13)
O4 C8 1.4225(13)
O1 C1 1.2037(13)
C1 C2 1.4911(16)
C4 C3 1.5046(16)
C4 C5 1.5110(14)
C4 H4 1.0000
C8 C9 1.5009(17)
C8 C10 1.5087(18)
C5 C6 1.5144(15)
C5 H5 1.0000
C7 C6 1.5395(16)
C7 H7 1.0000
C3 C2 1.5196(16)
C3 H3A 0.9900
C3 H3B 0.9900
C6 H6 1.0000
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C2 H2A 0.9900
C2 H2B 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
C5 O2 C1 O1 171.83(10)
C5 O2 C1 C2 -9.94(16)
C7 O3 C4 C3 160.58(9)
C7 O3 C4 C5 39.42(10)
C7 O4 C8 O5 31.22(11)
C7 O4 C8 C9 146.72(9)
C7 O4 C8 C10 -87.77(11)
C6 O5 C8 O4 -32.12(10)
C6 O5 C8 C9 -147.97(10)
C6 O5 C8 C10 86.70(11)
C1 O2 C5 C4 17.35(15)
C1 O2 C5 C6 130.69(10)
O3 C4 C5 O2 78.90(10)
C3 C4 C5 O2 -39.59(13)
O3 C4 C5 C6 -37.10(10)
C3 C4 C5 C6 -155.60(9)
C4 O3 C7 O4 87.82(10)
C4 O3 C7 C6 -25.15(11)
C8 O4 C7 O3 -132.88(9)
C8 O4 C7 C6 -18.14(11)
O3 C4 C3 C2 -61.41(12)
C5 C4 C3 C2 53.51(12)
C8 O5 C6 C5 131.59(9)
C8 O5 C6 C7 20.82(10)
O2 C5 C6 O5 149.53(8)
C4 C5 C6 O5 -89.50(9)
O2 C5 C6 C7 -99.12(9)
C4 C5 C6 C7 21.86(10)
O3 C7 C6 O5 115.39(9)
O4 C7 C6 O5 -1.80(11)
O3 C7 C6 C5 1.01(11)
O4 C7 C6 C5 -116.18(9)
O1 C1 C2 C3 -157.40(12)
O2 C1 C2 C3 24.49(16)
C4 C3 C2 C1 -45.61(14)
