#------------------------------------------------------------------------------
#$Date: 2019-11-28 20:10:21 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244483 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/89/7238969.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_7238969
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         'C12 H18 O5'
_chemical_formula_sum            'C12 H18 O5'
_chemical_formula_weight         242.26
_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                92.206(18)
_cell_angle_beta                 90.083(15)
_cell_angle_gamma                115.426(14)
_cell_formula_units_Z            2
_cell_length_a                   6.0548(19)
_cell_length_b                   6.2630(16)
_cell_length_c                   17.151(5)
_cell_measurement_reflns_used    3140
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      1.19
_cell_volume                     586.8(3)
_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 0.931
_diffrn_measured_fraction_theta_max 0.931
_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  0.0450
_diffrn_reflns_av_sigmaI/netI    0.1267
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3140
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.19
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             260
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .03
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2381
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1503
_refine_ls_R_factor_gt           0.0577
_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)+(0.0793P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1733
_reflns_number_gt                1226
_reflns_number_total             2381
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra40555a.txt
_cod_data_source_block           visk365
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7238969
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
O1 O 0.3933(4) 0.7014(4) 0.30039(12) 0.0263(6) Uani 1 1 d
O2 O 0.1671(4) 0.6168(4) 0.25176(12) 0.0271(6) Uani 1 1 d
O3 O 0.6297(4) 0.8949(4) 0.19513(12) 0.0236(6) Uani 1 1 d
O4 O 0.1780(5) 0.1933(4) 0.06625(14) 0.0314(7) Uani 1 1 d
O5 O -0.1959(4) 0.1463(4) 0.02747(13) 0.0250(6) Uani 1 1 d
C1 C 0.2380(7) 0.5558(6) 0.17658(18) 0.0234(8) Uani 1 1 d
C2 C 0.4227(7) 0.7848(6) 0.1441(2) 0.0237(8) Uani 1 1 d
C3 C 0.5663(6) 0.9261(5) 0.27417(18) 0.0237(9) Uani 1 1 d
C4 C 0.7956(7) 0.9742(7) 0.32162(19) 0.0254(9) Uani 1 1 d
C5 C 0.7729(8) 0.9879(6) 0.4103(2) 0.0278(9) Uani 1 1 d
C6 C 0.8215(8) 1.2306(6) 0.4452(2) 0.0302(9) Uani 1 1 d
C7 C 0.6879(8) 1.3575(6) 0.4053(2) 0.0316(9) Uani 1 1 d
C8 C 0.4464(7) 1.2015(6) 0.36401(19) 0.0278(9) Uani 1 1 d
C9 C 0.4698(7) 1.1141(6) 0.2812(2) 0.0255(9) Uani 1 1 d
C10 C 0.0121(6) 0.4417(5) 0.12583(18) 0.0212(8) Uani 1 1 d
C11 C 0.0064(7) 0.2490(5) 0.07120(18) 0.0228(8) Uani 1 1 d
C12 C -0.1672(8) 0.5093(7) 0.1268(2) 0.0293(9) Uani 1 1 d
H1 H 0.601(6) 0.871(5) 0.4237(16) 0.015(8) Uiso 1 1 d
H2 H 0.341(6) 1.061(5) 0.3952(17) 0.022(9) Uiso 1 1 d
H3 H 0.986(7) 1.327(5) 0.4445(17) 0.022(9) Uiso 1 1 d
H4 H 0.778(7) 1.214(6) 0.506(2) 0.042(10) Uiso 1 1 d
H5 H 0.309(7) 1.046(5) 0.2554(18) 0.025(9) Uiso 1 1 d
H6 H 0.491(6) 0.746(5) 0.0968(18) 0.021(9) Uiso 1 1 d
H7 H 0.337(6) 1.289(5) 0.3596(16) 0.017(8) Uiso 1 1 d
H8 H 0.885(7) 0.928(6) 0.435(2) 0.044(11) Uiso 1 1 d
H9 H 0.347(7) 0.894(6) 0.1331(19) 0.033(10) Uiso 1 1 d
H10 H 0.917(6) 1.118(6) 0.3064(18) 0.024(9) Uiso 1 1 d
H11 H 0.594(7) 1.253(6) 0.2530(19) 0.034(10) Uiso 1 1 d
H12 H 0.844(6) 0.846(6) 0.3039(18) 0.028(9) Uiso 1 1 d
H13 H 0.798(8) 1.465(7) 0.370(2) 0.055(13) Uiso 1 1 d
H14 H -0.308(7) 0.428(6) 0.0965(18) 0.028(10) Uiso 1 1 d
H15 H 0.660(8) 1.469(7) 0.447(2) 0.054(12) Uiso 1 1 d
H16 H 0.326(6) 0.449(5) 0.1821(17) 0.028(9) Uiso 1 1 d
H17 H -0.163(7) 0.642(6) 0.162(2) 0.045(11) Uiso 1 1 d
H18 H -0.178(7) 0.034(7) -0.004(2) 0.044(12) 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
C3 O1 O2 109.3(2)
C1 O2 O1 104.1(2)
C2 O3 C3 113.1(3)
C11 O5 H18 107(3)
O2 C1 C10 107.8(3)
O2 C1 C2 106.8(3)
C10 C1 C2 112.0(3)
O2 C1 H16 111.4(17)
C10 C1 H16 112.2(18)
C2 C1 H16 106.6(18)
O3 C2 C1 110.8(3)
O3 C2 H6 103.4(19)
C1 C2 H6 108.4(17)
O3 C2 H9 111.5(19)
C1 C2 H9 111(2)
H6 C2 H9 111(3)
O1 C3 O3 108.8(2)
O1 C3 C4 103.2(2)
O3 C3 C4 104.3(3)
O1 C3 C9 112.2(3)
O3 C3 C9 111.4(3)
C4 C3 C9 116.3(3)
C3 C4 C5 116.0(3)
C3 C4 H10 107(2)
C5 C4 H10 108.3(19)
C3 C4 H12 104.6(19)
C5 C4 H12 112.3(18)
H10 C4 H12 108(3)
C6 C5 C4 115.2(3)
C6 C5 H1 109.1(17)
C4 C5 H1 107.7(16)
C6 C5 H8 111(2)
C4 C5 H8 108(2)
H1 C5 H8 106(3)
C5 C6 C7 115.8(3)
C5 C6 H3 110(2)
C7 C6 H3 108(2)
C5 C6 H4 108.3(19)
C7 C6 H4 110(2)
H3 C6 H4 105(3)
C8 C7 C6 116.6(3)
C8 C7 H13 110(2)
C6 C7 H13 108(3)
C8 C7 H15 109(2)
C6 C7 H15 108(2)
H13 C7 H15 103(3)
C7 C8 C9 114.8(3)
C7 C8 H2 112.5(17)
C9 C8 H2 108.9(17)
C7 C8 H7 111.1(17)
C9 C8 H7 106.5(16)
H2 C8 H7 102(3)
C3 C9 C8 116.5(3)
C3 C9 H5 106.3(19)
C8 C9 H5 109.0(19)
C3 C9 H11 104(2)
C8 C9 H11 108.1(18)
H5 C9 H11 113(3)
C12 C10 C11 121.6(3)
C12 C10 C1 123.5(3)
C11 C10 C1 114.9(3)
O4 C11 O5 123.1(3)
O4 C11 C10 122.4(3)
O5 C11 C10 114.5(3)
C10 C12 H14 121(2)
C10 C12 H17 122(2)
H14 C12 H17 117(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.437(4)
O1 O2 1.481(3)
O2 C1 1.448(4)
O3 C2 1.421(4)
O3 C3 1.438(4)
O4 C11 1.232(4)
O5 C11 1.327(4)
O5 H18 0.91(4)
C1 C10 1.500(5)
C1 C2 1.518(5)
C1 H16 1.03(4)
C2 H6 0.98(3)
C2 H9 1.00(4)
C3 C4 1.517(5)
C3 C9 1.524(5)
C4 C5 1.529(5)
C4 H10 0.93(3)
C4 H12 1.00(4)
C5 C6 1.517(5)
C5 H1 1.02(3)
C5 H8 1.01(4)
C6 C7 1.532(5)
C6 H3 0.91(3)
C6 H4 1.08(4)
C7 C8 1.520(5)
C7 H13 0.96(4)
C7 H15 1.04(4)
C8 C9 1.532(5)
C8 H2 1.01(3)
C8 H7 1.03(3)
C9 H5 0.98(3)
C9 H11 1.01(4)
C10 C12 1.324(5)
C10 C11 1.487(5)
C12 H14 0.93(3)
C12 H17 1.00(4)
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 70.5(3)
O1 O2 C1 C10 173.6(2)
O1 O2 C1 C2 -65.9(3)
C3 O3 C2 C1 -52.6(4)
O2 C1 C2 O3 59.4(4)
C10 C1 C2 O3 177.2(3)
O2 O1 C3 O3 -62.8(3)
O2 O1 C3 C4 -173.1(2)
O2 O1 C3 C9 60.9(3)
C2 O3 C3 O1 54.0(3)
C2 O3 C3 C4 163.7(3)
C2 O3 C3 C9 -70.2(3)
O1 C3 C4 C5 -59.9(4)
O3 C3 C4 C5 -173.5(3)
C9 C3 C4 C5 63.5(4)
C3 C4 C5 C6 -87.7(4)
C4 C5 C6 C7 48.7(5)
C5 C6 C7 C8 27.5(5)
C6 C7 C8 C9 -83.1(4)
O1 C3 C9 C8 70.2(4)
O3 C3 C9 C8 -167.6(3)
C4 C3 C9 C8 -48.4(4)
C7 C8 C9 C3 72.0(4)
O2 C1 C10 C12 37.2(4)
C2 C1 C10 C12 -79.9(4)
O2 C1 C10 C11 -144.8(3)
C2 C1 C10 C11 98.0(3)
C12 C10 C11 O4 175.6(3)
C1 C10 C11 O4 -2.4(4)
C12 C10 C11 O5 -3.1(4)
C1 C10 C11 O5 178.9(2)
