#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/08/7150819.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_7150819
loop_
_publ_author_name
'Burton, Jonathan W.'
'Anderson, Edward A.'
'O'Sullivan, Paul T.'
'Collins, Ian'
'Davies, John E.'
'Bond, Andrew D.'
'Feeder, Neil'
'Holmes, Andrew B.'
_publ_section_title
;
 The Claisen rearrangement approach to fused bicyclic medium-ring
 oxacycles
;
_journal_issue                   4
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              693
_journal_page_last               702
_journal_paper_doi               10.1039/b715354f
_journal_volume                  6
_journal_year                    2008
_chemical_absolute_configuration
;
1147 Friedel pairs were averaged for the refinement
;
_chemical_formula_moiety         'C13 H16 O4'
_chemical_formula_sum            'C13 H16 O4'
_chemical_formula_weight         236.26
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.616(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.720(4)
_cell_length_b                   6.415(3)
_cell_length_c                   12.126(5)
_cell_measurement_reflns_used    3734
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.29
_cell_measurement_theta_min      3.2
_cell_volume                     596.5(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.883
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'thin slice / omega scans'
_diffrn_radiation_monochromator  'Si 111'
_diffrn_radiation_source         'Daresbury SRS, Station 9.8'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.68910
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_sigmaI/netI    0.0703
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4168
_diffrn_reflns_theta_full        29.63
_diffrn_reflns_theta_max         29.63
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9942
_exptl_absorpt_correction_T_min  0.9904
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1767
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0455
_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)+(0.0795P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1200
_reflns_number_gt                1584
_reflns_number_total             1767
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b715354f.txt
_cod_data_source_block           ah9911
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' tag value 'multi-scans' was replaced
with 'multi-scan' value.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        596.6(5)
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7150819
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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 0.1399(2) 1.4252(3) 0.73296(13) 0.0322(3) Uani 1 1 d . . .
O2 O 0.41870(19) 1.3847(2) 0.80408(11) 0.0272(3) Uani 1 1 d . . .
O3 O 0.60150(17) 0.9185(2) 0.70091(10) 0.0231(3) Uani 1 1 d . . .
O4 O 0.8442(2) 0.9142(4) 0.82073(12) 0.0459(5) Uani 1 1 d . . .
C1 C 0.2441(3) 1.3938(3) 0.81142(16) 0.0265(4) Uani 1 1 d . . .
C2 C 0.2064(3) 1.3516(4) 0.92799(17) 0.0368(5) Uani 1 1 d . . .
H2A H 0.0790 1.3383 0.9300 0.044 Uiso 1 1 calc R . .
H2B H 0.2491 1.4687 0.9769 0.044 Uiso 1 1 calc R . .
C3 C 0.2986(3) 1.1473(4) 0.96935(17) 0.0345(5) Uani 1 1 d . . .
H3A H 0.4259 1.1715 0.9830 0.041 Uiso 1 1 calc R . .
H3B H 0.2574 1.1052 1.0404 0.041 Uiso 1 1 calc R . .
C4 C 0.2624(3) 0.9748(4) 0.88593(18) 0.0305(4) Uani 1 1 d . . .
H4 H 0.1655 0.8873 0.8942 0.037 Uiso 1 1 calc R . .
C5 C 0.3530(3) 0.9327(3) 0.80145(16) 0.0256(4) Uani 1 1 d . . .
H5 H 0.3122 0.8212 0.7538 0.031 Uiso 1 1 calc R . .
C6 C 0.5127(2) 1.0446(3) 0.77475(16) 0.0218(4) Uani 1 1 d . . .
H6 H 0.5918 1.0685 0.8449 0.026 Uiso 1 1 calc R . .
C7 C 0.7737(3) 0.8903(4) 0.72869(16) 0.0269(4) Uani 1 1 d . . .
C8 C 0.8644(3) 0.8416(3) 0.62879(17) 0.0286(4) Uani 1 1 d . . .
H8A H 0.7872 0.7587 0.5746 0.034 Uiso 1 1 calc R . .
H8B H 0.9719 0.7604 0.6508 0.034 Uiso 1 1 calc R . .
C9 C 0.9100(3) 1.0534(3) 0.57678(18) 0.0281(4) Uani 1 1 d . . .
H9A H 0.9614 1.1469 0.6368 0.034 Uiso 1 1 calc R . .
H9B H 0.9995 1.0291 0.5260 0.034 Uiso 1 1 calc R . .
C10 C 0.7571(3) 1.1608(3) 0.51385(16) 0.0271(4) Uani 1 1 d . . .
H10 H 0.7405 1.1356 0.4361 0.032 Uiso 1 1 calc R . .
C11 C 0.6413(3) 1.2872(3) 0.55273(16) 0.0275(4) Uani 1 1 d . . .
H11 H 0.5545 1.3424 0.4987 0.033 Uiso 1 1 calc R . .
C12 C 0.6290(3) 1.3545(3) 0.67024(17) 0.0264(4) Uani 1 1 d . . .
H12A H 0.6182 1.5082 0.6729 0.032 Uiso 1 1 calc R . .
H12B H 0.7373 1.3145 0.7173 0.032 Uiso 1 1 calc R . .
C13 C 0.4732(2) 1.2553(3) 0.71609(15) 0.0220(4) Uani 1 1 d . . .
H13 H 0.3748 1.2390 0.6554 0.026 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 O2 C13 116.44(15) . . ?
C7 O3 C6 116.60(15) . . ?
O1 C1 O2 122.52(18) . . ?
O1 C1 C2 126.7(2) . . ?
O2 C1 C2 110.76(17) . . ?
C1 C2 C3 109.06(18) . . ?
C1 C2 H2A 109.9 . . ?
C3 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
C3 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
C4 C3 C2 111.25(19) . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 126.4(2) . . ?
C5 C4 H4 116.8 . . ?
C3 C4 H4 116.8 . . ?
C4 C5 C6 126.04(19) . . ?
C4 C5 H5 117.0 . . ?
C6 C5 H5 117.0 . . ?
O3 C6 C5 109.21(16) . . ?
O3 C6 C13 106.81(14) . . ?
C5 C6 C13 113.40(17) . . ?
O3 C6 H6 109.1 . . ?
C5 C6 H6 109.1 . . ?
C13 C6 H6 109.1 . . ?
O4 C7 O3 123.19(19) . . ?
O4 C7 C8 125.24(19) . . ?
O3 C7 C8 111.43(16) . . ?
C7 C8 C9 107.09(18) . . ?
C7 C8 H8A 110.3 . . ?
C9 C8 H8A 110.3 . . ?
C7 C8 H8B 110.3 . . ?
C9 C8 H8B 110.3 . . ?
H8A C8 H8B 108.6 . . ?
C10 C9 C8 114.01(18) . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C9 128.41(19) . . ?
C11 C10 H10 115.8 . . ?
C9 C10 H10 115.8 . . ?
C10 C11 C12 128.93(19) . . ?
C10 C11 H11 115.5 . . ?
C12 C11 H11 115.5 . . ?
C11 C12 C13 111.41(16) . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
O2 C13 C12 109.73(15) . . ?
O2 C13 C6 102.75(14) . . ?
C12 C13 C6 114.38(16) . . ?
O2 C13 H13 109.9 . . ?
C12 C13 H13 109.9 . . ?
C6 C13 H13 109.9 . . ?
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 1.190(3) . ?
O2 C1 1.363(2) . ?
O2 C13 1.452(2) . ?
O3 C7 1.346(2) . ?
O3 C6 1.438(2) . ?
O4 C7 1.194(3) . ?
C1 C2 1.500(3) . ?
C2 C3 1.547(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.504(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.333(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.494(3) . ?
C5 H5 0.9500 . ?
C6 C13 1.541(3) . ?
C6 H6 1.0000 . ?
C7 C8 1.500(3) . ?
C8 C9 1.555(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.498(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.333(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.502(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.522(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13 1.0000 . ?
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
C13 O2 C1 O1 -48.1(3) . . . . ?
C13 O2 C1 C2 129.77(19) . . . . ?
O1 C1 C2 C3 126.5(2) . . . . ?
O2 C1 C2 C3 -51.3(3) . . . . ?
C1 C2 C3 C4 -49.0(3) . . . . ?
C2 C3 C4 C5 87.7(3) . . . . ?
C3 C4 C5 C6 2.1(4) . . . . ?
C7 O3 C6 C5 -130.66(18) . . . . ?
C7 O3 C6 C13 106.34(18) . . . . ?
C4 C5 C6 O3 162.68(19) . . . . ?
C4 C5 C6 C13 -78.3(3) . . . . ?
C6 O3 C7 O4 20.5(3) . . . . ?
C6 O3 C7 C8 -155.38(17) . . . . ?
O4 C7 C8 C9 -89.8(3) . . . . ?
O3 C7 C8 C9 85.9(2) . . . . ?
C7 C8 C9 C10 -75.6(2) . . . . ?
C8 C9 C10 C11 85.4(3) . . . . ?
C9 C10 C11 C12 -1.2(4) . . . . ?
C10 C11 C12 C13 -109.0(2) . . . . ?
C1 O2 C13 C12 144.42(17) . . . . ?
C1 O2 C13 C6 -93.53(18) . . . . ?
C11 C12 C13 O2 -154.87(16) . . . . ?
C11 C12 C13 C6 90.3(2) . . . . ?
O3 C6 C13 O2 -168.45(14) . . . . ?
C5 C6 C13 O2 71.20(18) . . . . ?
O3 C6 C13 C12 -49.6(2) . . . . ?
C5 C6 C13 C12 -169.95(16) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21195402
2 PubChem 101025015
