#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/33/7103319.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_7103319
loop_
_publ_author_name
'Fyvie, W Sean'
'Peczuh, Mark W'
_publ_section_title
;
 Remote induction of asymmetry in [13]-macro-dilactone topology by a
 single stereogenic center.
;
_journal_issue                   34
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4028
_journal_page_last               4030
_journal_paper_doi               10.1039/b807562j
_journal_year                    2008
_chemical_absolute_configuration syn
_chemical_formula_sum            'C15 H22 O5'
_chemical_formula_weight         282.33
_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                   6.4153(13)
_cell_length_b                   12.269(3)
_cell_length_c                   18.605(4)
_cell_measurement_temperature    173(2)
_cell_volume                     1464.4(5)
_computing_cell_refinement       Denzo
_computing_data_collection       'Nonius Collect'
_computing_data_reduction        Denzo
_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      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω 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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1341
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            3801
_diffrn_reflns_theta_full        28.97
_diffrn_reflns_theta_max         28.97
_diffrn_reflns_theta_min         3.32
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9924
_exptl_absorpt_correction_T_min  0.9859
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3801
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1525
_refine_ls_R_factor_gt           0.0586
_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)+(0.0330P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                2021
_reflns_number_total             3801
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b807562j.txt
_cod_data_source_block           mp08
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7103319
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6662(2) 0.46869(12) 0.20280(8) 0.0291(4) Uani 1 1 d . . .
O2 O 0.3324(3) 0.41348(13) 0.20603(9) 0.0379(4) Uani 1 1 d . . .
O3 O 0.1174(3) 0.40800(14) -0.01143(9) 0.0493(5) Uani 1 1 d . . .
O4 O 0.5892(2) 0.63290(14) 0.04353(8) 0.0348(5) Uani 1 1 d . . .
O5 O 0.5231(2) 0.69969(12) 0.15381(8) 0.0286(4) Uani 1 1 d . . .
C1 C 0.5039(4) 0.40954(19) 0.17933(12) 0.0284(6) Uani 1 1 d . . .
C2 C 0.5622(4) 0.33781(19) 0.11692(12) 0.0342(7) Uani 1 1 d . . .
H2A H 0.6177 0.2679 0.1353 0.041 Uiso 1 1 calc R . .
H2B H 0.6737 0.3736 0.0887 0.041 Uiso 1 1 calc R . .
C3 C 0.3754(4) 0.3150(2) 0.06779(13) 0.0376(7) Uani 1 1 d . . .
H3A H 0.4097 0.2538 0.0352 0.045 Uiso 1 1 calc R . .
H3B H 0.2545 0.2929 0.0975 0.045 Uiso 1 1 calc R . .
C4 C 0.3180(4) 0.4130(2) 0.02397(12) 0.0345(6) Uani 1 1 d . . .
H4A H 0.4336 0.4454 -0.0051 0.041 Uiso 1 1 calc R . .
C5 C 0.1517(4) 0.48842(19) 0.04436(13) 0.0317(6) Uani 1 1 d . . .
H5A H 0.0824 0.4734 0.0915 0.038 Uiso 1 1 calc R . .
C6 C 0.1475(4) 0.60500(19) 0.01963(12) 0.0302(6) Uani 1 1 d . . .
H6A H 0.0017 0.6266 0.0095 0.036 Uiso 1 1 calc R . .
H6B H 0.2278 0.6117 -0.0256 0.036 Uiso 1 1 calc R . .
C7 C 0.2392(4) 0.6817(2) 0.07568(12) 0.0281(6) Uani 1 1 d . . .
H7A H 0.2134 0.7578 0.0604 0.034 Uiso 1 1 calc R . .
H7B H 0.1658 0.6702 0.1219 0.034 Uiso 1 1 calc R . .
C8 C 0.4664(4) 0.66676(19) 0.08736(12) 0.0247(6) Uani 1 1 d . . .
C9 C 0.7416(3) 0.6889(2) 0.17247(12) 0.0305(6) Uani 1 1 d . . .
H9A H 0.8108 0.7609 0.1692 0.037 Uiso 1 1 calc R . .
H9B H 0.8110 0.6389 0.1383 0.037 Uiso 1 1 calc R . .
C10 C 0.7619(4) 0.6447(2) 0.24847(12) 0.0253(6) Uani 1 1 d . . .
H10A H 0.7159 0.7034 0.2822 0.030 Uiso 1 1 calc R . .
C11 C 0.6238(4) 0.54618(18) 0.26135(11) 0.0281(6) Uani 1 1 d . . .
H11A H 0.4746 0.5693 0.2588 0.034 Uiso 1 1 calc R . .
C12 C 0.6629(4) 0.4914(2) 0.33332(12) 0.0337(6) Uani 1 1 d . . .
H12A H 0.5852 0.4217 0.3350 0.040 Uiso 1 1 calc R . .
H12B H 0.6089 0.5386 0.3722 0.040 Uiso 1 1 calc R . .
C13 C 0.8934(4) 0.4688(2) 0.34663(13) 0.0361(6) Uani 1 1 d . . .
H13A H 0.9117 0.4388 0.3956 0.043 Uiso 1 1 calc R . .
H13B H 0.9434 0.4137 0.3118 0.043 Uiso 1 1 calc R . .
C14 C 1.0219(4) 0.5719(2) 0.33896(13) 0.0354(6) Uani 1 1 d . . .
H14A H 1.1711 0.5549 0.3466 0.042 Uiso 1 1 calc R . .
H14B H 0.9787 0.6254 0.3759 0.042 Uiso 1 1 calc R . .
C15 C 0.9920(4) 0.6212(2) 0.26401(12) 0.0311(6) Uani 1 1 d . . .
H15A H 1.0725 0.6899 0.2605 0.037 Uiso 1 1 calc R . .
H15B H 1.0467 0.5701 0.2274 0.037 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
C1 O1 C11 116.56(17) . . ?
C4 O3 C5 60.65(14) . . ?
C8 O5 C9 116.87(18) . . ?
O2 C1 O1 123.4(2) . . ?
O2 C1 C2 124.6(2) . . ?
O1 C1 C2 112.0(2) . . ?
C1 C2 C3 111.9(2) . . ?
C4 C3 C2 111.7(2) . . ?
O3 C4 C5 59.74(15) . . ?
O3 C4 C3 115.6(2) . . ?
C5 C4 C3 123.1(2) . . ?
O3 C5 C4 59.61(15) . . ?
O3 C5 C6 115.22(19) . . ?
C4 C5 C6 122.4(2) . . ?
C5 C6 C7 111.81(19) . . ?
C8 C7 C6 113.8(2) . . ?
O4 C8 O5 123.1(2) . . ?
O4 C8 C7 125.7(2) . . ?
O5 C8 C7 111.2(2) . . ?
O5 C9 C10 109.75(18) . . ?
C11 C10 C9 112.40(19) . . ?
C11 C10 C15 112.5(2) . . ?
C9 C10 C15 108.99(19) . . ?
O1 C11 C10 106.86(18) . . ?
O1 C11 C12 109.63(18) . . ?
C10 C11 C12 113.29(19) . . ?
C11 C12 C13 112.5(2) . . ?
C14 C13 C12 111.1(2) . . ?
C13 C14 C15 110.3(2) . . ?
C10 C15 C14 111.51(19) . . ?
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 C1 1.342(3) . ?
O1 C11 1.471(3) . ?
O2 C1 1.208(3) . ?
O3 C4 1.447(3) . ?
O3 C5 1.449(3) . ?
O4 C8 1.207(3) . ?
O5 C8 1.351(3) . ?
O5 C9 1.451(3) . ?
C1 C2 1.504(3) . ?
C2 C3 1.533(3) . ?
C3 C4 1.499(3) . ?
C4 C5 1.462(3) . ?
C5 C6 1.503(3) . ?
C6 C7 1.523(3) . ?
C7 C8 1.485(3) . ?
C9 C10 1.520(3) . ?
C10 C11 1.518(3) . ?
C10 C15 1.531(3) . ?
C11 C12 1.519(3) . ?
C12 C13 1.524(3) . ?
C13 C14 1.517(3) . ?
C14 C15 1.532(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653053
