#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/69/1506920.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_1506920
loop_
_publ_author_name
'Kelly, T. Ross'
'Cai, Xiaolu'
'Tu, Bin'
'Elliott, Eric L.'
'Grossmann, Gilles'
'Laurent, Pierre'
_publ_section_title
;
 Asymmetric synthesis of the AB ring system of lactonamycin.
;
_journal_issue                   26
_journal_name_full               'Organic letters'
_journal_page_first              4953
_journal_page_last               4956
_journal_paper_doi               10.1021/ol047922h
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C8 H10 O8'
_chemical_formula_weight         234.16
_chemical_name_systematic
; 
 ? 
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3616(6)
_cell_length_b                   10.4148(7)
_cell_length_c                   11.2854(7)
_cell_measurement_reflns_used    5142
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.66
_cell_volume                     982.78(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6767
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2429
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0340
_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)+(0.0623P)²+0.1205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0942
_reflns_number_gt                2361
_reflns_number_total             2429
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol047922hsi20041008_035904.cif
_cod_data_source_block           38
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1506920
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
O3 O 0.12947(12) 0.12417(10) 0.12168(9) 0.0285(2) Uani 1 1 d .
H3A H 0.1050 0.1236 0.0495 0.043 Uiso 1 1 calc R
O5 O 0.17612(15) -0.13393(10) 0.18987(9) 0.0324(2) Uani 1 1 d .
O6 O 0.33847(13) 0.18260(10) -0.04795(8) 0.0273(2) Uani 1 1 d .
H6A H 0.2408 0.1640 -0.0503 0.041 Uiso 1 1 calc R
O7 O 0.60487(14) 0.04939(11) -0.06722(9) 0.0321(2) Uani 1 1 d .
O4 O 0.33262(14) -0.12870(10) 0.02925(9) 0.0332(2) Uani 1 1 d .
O1 O 0.49545(13) 0.35538(10) 0.10827(10) 0.0320(2) Uani 1 1 d .
O8 O 0.62885(12) 0.02659(10) 0.13084(9) 0.0288(2) Uani 1 1 d .
O2 O 0.40992(14) 0.22591(10) 0.25178(8) 0.0298(2) Uani 1 1 d .
C3 C 0.28100(15) 0.06691(13) 0.13680(11) 0.0211(2) Uani 1 1 d .
C2 C 0.40360(15) 0.13917(12) 0.05822(11) 0.0206(2) Uani 1 1 d .
C5 C 0.55866(15) 0.06461(13) 0.03200(12) 0.0235(3) Uani 1 1 d .
C1 C 0.44314(15) 0.25380(13) 0.13941(12) 0.0245(3) Uani 1 1 d .
C7 C 0.26990(16) -0.07684(13) 0.11170(11) 0.0229(3) Uani 1 1 d .
C4 C 0.33665(19) 0.09927(13) 0.26145(11) 0.0269(3) Uani 1 1 d .
H4A H 0.2451 0.1012 0.3170 0.032 Uiso 1 1 calc R
H4B H 0.4153 0.0353 0.2899 0.032 Uiso 1 1 calc R
C6 C 0.77879(18) -0.04263(17) 0.11693(16) 0.0353(3) Uani 1 1 d .
H6B H 0.8202 -0.0665 0.1951 0.053 Uiso 1 1 calc R
H6C H 0.8566 0.0123 0.0764 0.053 Uiso 1 1 calc R
H6D H 0.7605 -0.1204 0.0699 0.053 Uiso 1 1 calc R
C8 C 0.1459(2) -0.26979(15) 0.16739(15) 0.0382(3) Uani 1 1 d .
H8A H 0.0755 -0.3041 0.2292 0.057 Uiso 1 1 calc R
H8B H 0.2474 -0.3168 0.1680 0.057 Uiso 1 1 calc R
H8C H 0.0946 -0.2797 0.0899 0.057 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
C7 O5 C8 115.01(12)
C5 O8 C6 116.12(11)
C1 O2 C4 110.88(10)
O3 C3 C4 107.05(11)
O3 C3 C7 109.73(11)
C4 C3 C7 114.08(11)
O3 C3 C2 108.63(10)
C4 C3 C2 102.67(10)
C7 C3 C2 114.21(11)
O6 C2 C5 109.14(10)
O6 C2 C1 110.12(11)
C5 C2 C1 108.92(10)
O6 C2 C3 113.05(10)
C5 C2 C3 114.95(11)
C1 C2 C3 100.24(10)
O7 C5 O8 127.42(12)
O7 C5 C2 121.27(12)
O8 C5 C2 111.28(10)
O1 C1 O2 123.29(13)
O1 C1 C2 126.05(13)
O2 C1 C2 110.66(11)
O4 C7 O5 125.16(13)
O4 C7 C3 124.07(12)
O5 C7 C3 110.70(11)
O2 C4 C3 105.07(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C3 1.4107(16)
O5 C7 1.3216(16)
O5 C8 1.4595(18)
O6 C2 1.3917(15)
O7 C5 1.1951(17)
O4 C7 1.1969(17)
O1 C1 1.1975(18)
O8 C5 1.3212(16)
O8 C6 1.4548(18)
O2 C1 1.3304(17)
O2 C4 1.4583(17)
C3 C4 1.5195(18)
C3 C7 1.5266(18)
C3 C2 1.5504(17)
C2 C5 1.5400(18)
C2 C1 1.5408(17)
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
O3 C3 C2 O6 -34.56(14)
C4 C3 C2 O6 -147.70(11)
C7 C3 C2 O6 88.27(13)
O3 C3 C2 C5 -160.79(10)
C4 C3 C2 C5 86.07(13)
C7 C3 C2 C5 -37.96(15)
O3 C3 C2 C1 82.62(12)
C4 C3 C2 C1 -30.52(12)
C7 C3 C2 C1 -154.54(11)
C6 O8 C5 O7 -0.6(2)
C6 O8 C5 C2 -178.71(12)
O6 C2 C5 O7 -1.21(18)
C1 C2 C5 O7 -121.48(14)
C3 C2 C5 O7 127.00(14)
O6 C2 C5 O8 177.05(10)
C1 C2 C5 O8 56.79(14)
C3 C2 C5 O8 -54.74(15)
C4 O2 C1 O1 175.63(13)
C4 O2 C1 C2 -3.87(15)
O6 C2 C1 O1 -37.87(18)
C5 C2 C1 O1 81.79(16)
C3 C2 C1 O1 -157.21(13)
O6 C2 C1 O2 141.61(11)
C5 C2 C1 O2 -98.74(12)
C3 C2 C1 O2 22.27(13)
C8 O5 C7 O4 -2.3(2)
C8 O5 C7 C3 174.72(13)
O3 C3 C7 O4 112.72(15)
C4 C3 C7 O4 -127.18(14)
C2 C3 C7 O4 -9.51(19)
O3 C3 C7 O5 -64.34(13)
C4 C3 C7 O5 55.75(15)
C2 C3 C7 O5 173.42(11)
C1 O2 C4 C3 -16.98(15)
O3 C3 C4 O2 -84.39(12)
C7 C3 C4 O2 154.03(11)
C2 C3 C4 O2 29.91(13)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21200147 ChemSpider
