#------------------------------------------------------------------------------
#$Date: 2019-11-28 20:10:21 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244483 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/89/7238967.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_7238967
loop_
_publ_author_name
'Griesbeck, Axel G.'
'Schlundt, Viktor'
'Neudörfl, Jörg M.'
_publ_section_title
;
 Functionalized polar 1,2,4-trioxanes as building blocks by singlet
 oxygenation of 4-hydroxy tiglic acid using the solvent deuterium isotope
 trick
;
_journal_issue                   20
_journal_name_full               'RSC Advances'
_journal_page_first              7265
_journal_paper_doi               10.1039/c3ra40555a
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C8 H12 O5'
_chemical_formula_sum            'C8 H12 O5'
_chemical_formula_weight         188.18
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.770(6)
_cell_angle_beta                 99.179(6)
_cell_angle_gamma                117.482(5)
_cell_formula_units_Z            2
_cell_length_a                   5.8622(5)
_cell_length_b                   5.9939(5)
_cell_length_c                   14.537(2)
_cell_measurement_reflns_used    2608
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.86
_cell_volume                     444.15(8)
_computing_cell_refinement       'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       Phi/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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0575
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2608
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.86
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             200
_exptl_crystal_size_max          .6
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .1
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1901
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0406
_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)+(0.0493P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1066
_reflns_number_gt                1440
_reflns_number_total             1901
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra40555a.txt
_cod_data_source_block           visk201
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7238967
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O1 O 0.73292(18) 0.71893(17) 0.31850(7) 0.0238(3) Uani 1 1 d .
O2 O 0.83323(18) 0.95622(18) 0.38149(7) 0.0228(3) Uani 1 1 d .
O3 O 1.02316(18) 1.19533(16) 0.26511(6) 0.0210(3) Uani 1 1 d .
O4 O 0.23166(19) 0.69026(18) 0.08495(7) 0.0275(3) Uani 1 1 d .
O5 O 0.1720(2) 0.31019(18) 0.03009(7) 0.0243(3) Uani 1 1 d .
H1 H 0.040(4) 0.312(3) -0.0071(13) 0.044(5) Uiso 1 1 d .
C1 C 1.0759(3) 1.1408(3) 0.35872(10) 0.0204(3) Uani 1 1 d .
C2 C 0.8932(3) 0.9756(2) 0.19751(10) 0.0206(3) Uani 1 1 d .
H2A H 1.0133 0.9046 0.1911 0.025 Uiso 1 1 calc R
H2B H 0.8429 1.0222 0.1357 0.025 Uiso 1 1 calc R
C3 C 0.6500(3) 0.7784(3) 0.22803(9) 0.0193(3) Uani 1 1 d .
H3 H 0.5267 0.8485 0.2331 0.023 Uiso 1 1 calc R
C4 C 0.5140(2) 0.5395(3) 0.16076(9) 0.0198(3) Uani 1 1 d .
C5 C 0.2932(2) 0.5209(2) 0.08907(10) 0.0196(3) Uani 1 1 d .
C6 C 0.5847(3) 0.3594(3) 0.16246(11) 0.0273(4) Uani 1 1 d .
H6A H 0.4934 0.2139 0.1171 0.033 Uiso 1 1 calc R
H6B H 0.7266 0.3754 0.2090 0.033 Uiso 1 1 calc R
C7 C 1.1483(3) 1.3762(3) 0.42207(11) 0.0265(4) Uani 1 1 d .
H7A H 1.3103 1.5153 0.4099 0.040 Uiso 1 1 calc R
H7B H 1.1751 1.3449 0.4877 0.040 Uiso 1 1 calc R
H7C H 1.0067 1.4218 0.4099 0.040 Uiso 1 1 calc R
C8 C 1.2825(3) 1.0538(3) 0.37295(11) 0.0263(4) Uani 1 1 d .
H8A H 1.2204 0.8959 0.3320 0.039 Uiso 1 1 calc R
H8B H 1.3159 1.0250 0.4386 0.039 Uiso 1 1 calc R
H8C H 1.4448 1.1842 0.3575 0.039 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0274(5) 0.0212(5) 0.0178(5) -0.0006(4) 0.0017(4) 0.0084(4)
O2 0.0215(5) 0.0245(5) 0.0188(5) -0.0040(4) 0.0042(4) 0.0081(4)
O3 0.0245(5) 0.0190(5) 0.0191(5) 0.0001(4) 0.0026(4) 0.0105(4)
O4 0.0295(5) 0.0248(5) 0.0281(6) -0.0054(5) -0.0038(4) 0.0163(5)
O5 0.0262(5) 0.0213(6) 0.0228(6) -0.0040(4) -0.0028(4) 0.0117(5)
C1 0.0183(6) 0.0231(7) 0.0207(7) 0.0016(6) 0.0041(5) 0.0105(6)
C2 0.0232(7) 0.0203(7) 0.0181(7) -0.0007(6) 0.0052(5) 0.0099(6)
C3 0.0201(6) 0.0239(7) 0.0161(7) 0.0012(6) 0.0024(5) 0.0127(6)
C4 0.0190(7) 0.0204(7) 0.0194(7) 0.0011(6) 0.0057(5) 0.0083(6)
C5 0.0217(7) 0.0173(7) 0.0193(7) 0.0007(6) 0.0061(6) 0.0084(6)
C6 0.0270(8) 0.0263(8) 0.0273(8) -0.0016(7) -0.0001(6) 0.0135(7)
C7 0.0287(8) 0.0270(8) 0.0248(8) -0.0042(6) 0.0011(6) 0.0157(7)
C8 0.0226(7) 0.0284(8) 0.0297(8) 0.0005(7) 0.0020(6) 0.0147(6)
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
C3 O1 O2 104.09(9)
C1 O2 O1 108.61(9)
C2 O3 C1 113.42(10)
C5 O5 H1 108.3(11)
O3 C1 O2 108.64(10)
O3 C1 C7 106.18(11)
O2 C1 C7 103.71(11)
O3 C1 C8 112.69(11)
O2 C1 C8 111.68(12)
C7 C1 C8 113.38(12)
O3 C2 C3 109.91(11)
O3 C2 H2A 109.7
C3 C2 H2A 109.7
O3 C2 H2B 109.7
C3 C2 H2B 109.7
H2A C2 H2B 108.2
O1 C3 C4 108.37(11)
O1 C3 C2 107.57(11)
C4 C3 C2 111.53(11)
O1 C3 H3 109.8
C4 C3 H3 109.8
C2 C3 H3 109.8
C6 C4 C5 121.52(12)
C6 C4 C3 123.81(13)
C5 C4 C3 114.65(12)
O4 C5 O5 123.11(13)
O4 C5 C4 122.06(12)
O5 C5 C4 114.83(12)
C4 C6 H6A 120.0
C4 C6 H6B 120.0
H6A C6 H6B 120.0
C1 C7 H7A 109.5
C1 C7 H7B 109.5
H7A C7 H7B 109.5
C1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C1 C8 H8A 109.5
C1 C8 H8B 109.5
H8A C8 H8B 109.5
C1 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.4416(17)
O1 O2 1.4775(13)
O2 C1 1.4412(16)
O3 C2 1.4268(15)
O3 C1 1.4285(17)
O4 C5 1.2240(17)
O5 C5 1.3214(16)
O5 H1 0.87(2)
C1 C7 1.504(2)
C1 C8 1.513(2)
C2 C3 1.5180(18)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.5015(19)
C3 H3 1.0000
C4 C6 1.322(2)
C4 C5 1.485(2)
C6 H6A 0.9500
C6 H6B 0.9500
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
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
C3 O1 O2 C1 -70.56(12)
C2 O3 C1 O2 -55.19(14)
C2 O3 C1 C7 -166.19(10)
C2 O3 C1 C8 69.12(14)
O1 O2 C1 O3 63.67(13)
O1 O2 C1 C7 176.31(9)
O1 O2 C1 C8 -61.24(13)
C1 O3 C2 C3 52.52(15)
O2 O1 C3 C4 -173.21(9)
O2 O1 C3 C2 66.08(12)
O3 C2 C3 O1 -58.78(15)
O3 C2 C3 C4 -177.48(10)
O1 C3 C4 C6 -35.83(18)
C2 C3 C4 C6 82.40(17)
O1 C3 C4 C5 145.50(11)
C2 C3 C4 C5 -96.28(14)
C6 C4 C5 O4 -177.56(13)
C3 C4 C5 O4 1.15(19)
C6 C4 C5 O5 1.69(19)
C3 C4 C5 O5 -179.61(10)
