#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/73/1507323.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_1507323
loop_
_publ_author_name
'Su, Qibin'
'Beeler, Aaron B.'
'Lobkovsky, Emil'
'Porco, Jr, John A'
'Panek, James S.'
_publ_section_title
;
 Stereochemical diversity through cyclodimerization: synthesis of
 polyketide-like macrodiolides.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2149
_journal_page_last               2152
_journal_paper_doi               10.1021/ol034608z
_journal_volume                  5
_journal_year                    2003
_chemical_formula_sum            'C14 H20 O4'
_chemical_formula_weight         252.30
_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   difmap
_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                   4.7958(5)
_cell_length_b                   16.711(2)
_cell_length_c                   17.195(2)
_cell_measurement_temperature    173(2)
_cell_volume                     1378.1(3)
_computing_cell_refinement       SAINT+
_computing_data_collection       SMART
_computing_data_reduction        SAINT+
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.925
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device_type  'Bruker 1K CCD'
_diffrn_measurement_method       '0.3 deg. omega scan'
_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  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4805
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.7409
_exptl_absorpt_correction_type   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.1(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    isotropic
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         2567
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.082
_refine_ls_shift/su_mean         0.017
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0577P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                2005
_reflns_number_total             2567
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol034608zsi20030408_064926.cif
_cod_data_source_block           porco9
_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_cell_volume        1378.0(3)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1507323
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
O1 O -0.2407(5) 0.16487(12) 0.84002(12) 0.0711(7) Uani 1 1 d
O2 O -0.0678(3) 0.26846(9) 0.77587(8) 0.0370(4) Uani 1 1 d
O3 O -0.2869(4) 0.61680(10) 0.85269(11) 0.0482(5) Uani 1 1 d
O4 O -0.0060(3) 0.51043(9) 0.84351(9) 0.0330(4) Uani 1 1 d
C1 C -0.0872(5) 0.22067(13) 0.83702(13) 0.0340(5) Uani 1 1 d
C2 C -0.2474(7) 0.24949(15) 0.71019(14) 0.0385(6) Uani 1 1 d
H2B H -0.186(6) 0.2022(14) 0.6860(14) 0.038(7) Uiso 1 1 d
H2A H -0.451(7) 0.2415(16) 0.7287(16) 0.057(8) Uiso 1 1 d
C3 C -0.2368(6) 0.31877(14) 0.65439(13) 0.0338(5) Uani 1 1 d
H3 H -0.035(5) 0.3242(12) 0.6429(12) 0.023(6) Uiso 1 1 d
C4 C -0.3519(6) 0.39301(15) 0.68941(13) 0.0339(5) Uani 1 1 d
H4 H -0.553(6) 0.3825(15) 0.7034(15) 0.048(7) Uiso 1 1 d
C5 C -0.2126(6) 0.45850(15) 0.70618(12) 0.0346(6) Uani 1 1 d
H5 H -0.002(6) 0.4550(16) 0.6940(14) 0.048(7) Uiso 1 1 d
C6 C -0.3286(7) 0.53290(15) 0.74059(15) 0.0406(6) Uani 1 1 d
H6B H -0.516(7) 0.5272(17) 0.751(2) 0.064(10) Uiso 1 1 d
H6A H -0.314(7) 0.5877(18) 0.706(2) 0.084(11) Uiso 1 1 d
C7 C -0.2077(5) 0.55911(13) 0.81764(14) 0.0335(5) Uani 1 1 d
C8 C 0.1034(6) 0.53027(14) 0.91974(13) 0.0325(6) Uani 1 1 d
H8B H 0.200(5) 0.5884(14) 0.9178(14) 0.041(7) Uiso 1 1 d
H8A H -0.049(6) 0.5348(13) 0.9564(14) 0.034(7) Uiso 1 1 d
C9 C 0.3054(5) 0.46497(13) 0.94490(12) 0.0300(5) Uani 1 1 d
H9 H 0.461(4) 0.4610(11) 0.9094(11) 0.016(5) Uiso 1 1 d
C10 C 0.1751(5) 0.38338(13) 0.94629(12) 0.0307(5) Uani 1 1 d
H10 H 0.035(6) 0.3687(15) 0.9863(16) 0.054(8) Uiso 1 1 d
C11 C 0.2342(5) 0.32491(13) 0.89811(13) 0.0301(5) Uani 1 1 d
H11 H 0.375(6) 0.3286(14) 0.8593(16) 0.041(7) Uiso 1 1 d
C12 C 0.1069(7) 0.24334(15) 0.90205(14) 0.0367(6) Uani 1 1 d
H12B H 0.238(6) 0.2052(16) 0.9020(16) 0.048(8) Uiso 1 1 d
H12A H -0.008(6) 0.2399(15) 0.9484(17) 0.052(8) Uiso 1 1 d
C13 C -0.3903(7) 0.29499(18) 0.57976(14) 0.0422(7) Uani 1 1 d
H13C H -0.311(6) 0.2416(17) 0.5593(15) 0.053(8) Uiso 1 1 d
H13B H -0.369(6) 0.3324(16) 0.5442(17) 0.053(8) Uiso 1 1 d
H13A H -0.583(6) 0.2798(15) 0.5901(14) 0.043(8) Uiso 1 1 d
C14 C 0.4160(7) 0.48783(17) 1.02558(15) 0.0409(6) Uani 1 1 d
H14C H 0.580(7) 0.4467(17) 1.0439(16) 0.056(8) Uiso 1 1 d
H14B H 0.264(6) 0.4896(15) 1.0629(15) 0.042(7) Uiso 1 1 d
H14A H 0.497(7) 0.5423(17) 1.0230(16) 0.058(8) Uiso 1 1 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 0.0016 '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 C2 116.34(18)
C7 O4 C8 115.00(17)
O1 C1 O2 123.4(2)
O1 C1 C12 123.3(2)
O2 C1 C12 113.3(2)
O2 C2 C3 107.9(2)
C4 C3 C2 111.8(2)
C4 C3 C13 112.2(2)
C2 C3 C13 108.6(2)
C5 C4 C3 126.6(2)
C4 C5 C6 126.5(3)
C5 C6 C7 116.6(2)
O3 C7 O4 123.4(2)
O3 C7 C6 123.5(2)
O4 C7 C6 113.1(2)
O4 C8 C9 108.86(17)
C10 C9 C8 113.0(2)
C10 C9 C14 110.86(19)
C8 C9 C14 107.4(2)
C11 C10 C9 125.2(2)
C10 C11 C12 124.2(2)
C11 C12 C1 116.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.189(3)
O2 C1 1.324(3)
O2 C2 1.455(3)
O3 C7 1.199(3)
O4 C7 1.340(3)
O4 C8 1.450(3)
C1 C12 1.503(3)
C2 C3 1.505(3)
C3 C4 1.485(3)
C3 C13 1.532(3)
C4 C5 1.314(3)
C5 C6 1.485(4)
C6 C7 1.511(4)
C8 C9 1.522(3)
C9 C10 1.500(3)
C9 C14 1.534(3)
C10 C11 1.312(3)
C11 C12 1.495(3)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21200332 ChemSpider
