#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:24:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178468 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/89/4028991.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_4028991
loop_
_publ_author_name
'Eske, Angelika'
'Goldfuss, Bernd'
'Griesbeck, Axel G.'
'de Kiff, Alan'
'Kleczka, Margarethe'
'Leven, Matthias'
'Neudörfl, Jörg-M'
'Vollmer, Moritz'
_publ_section_title
;
 Ene-diene transmissive cycloaddition reactions with singlet oxygen: the
 vinylogous gem effect and its use for polyoxyfunctionalization of dienes.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1818
_journal_page_last               1829
_journal_paper_doi               10.1021/jo5000434
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C9 H14 O4'
_chemical_formula_sum            'C9 H14 O4'
_chemical_formula_weight         186.20
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   6.0161(4)
_cell_length_b                   14.424(2)
_cell_length_c                   21.643(3)
_cell_measurement_reflns_used    6840
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.82
_cell_volume                     1878.1(4)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0548
_diffrn_reflns_av_sigmaI/netI    0.0762
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6840
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          .4
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .1
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2033
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0251P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0785
_reflns_number_gt                1247
_reflns_number_total             2033
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5000434_si_001.cif
_cod_data_source_block           mag108
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4028991
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
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 0.59456(15) 0.28779(8) 0.10909(5) 0.0240(3) Uani 1 1 d .
O2 O 0.43597(15) 0.28436(8) 0.16105(5) 0.0216(3) Uani 1 1 d .
O3 O 0.47595(15) 0.10201(8) 0.16084(5) 0.0220(3) Uani 1 1 d .
O4 O 0.18933(16) 0.08180(8) 0.09538(5) 0.0263(3) Uani 1 1 d .
C1 C 0.2468(2) 0.23331(12) 0.13922(7) 0.0187(4) Uani 1 1 d .
C2 C 0.3011(2) 0.13155(12) 0.12821(7) 0.0190(4) Uani 1 1 d .
C3 C 0.5314(3) 0.00398(12) 0.15431(9) 0.0229(4) Uani 1 1 d .
C4 C 0.7249(2) -0.01429(12) 0.19648(7) 0.0280(4) Uani 1 1 d .
H4A H 0.8498 0.0255 0.1847 0.042 Uiso 1 1 calc R
H4B H 0.7693 -0.0795 0.1930 0.042 Uiso 1 1 calc R
H4C H 0.6817 -0.0009 0.2392 0.042 Uiso 1 1 calc R
C5 C 0.1579(3) 0.27824(12) 0.08144(7) 0.0190(4) Uani 1 1 d .
C6 C 0.2764(2) 0.33864(11) 0.04912(7) 0.0184(4) Uani 1 1 d .
C7 C 0.5115(3) 0.35734(13) 0.06768(9) 0.0215(4) Uani 1 1 d .
C8 C 0.1920(2) 0.39331(12) -0.00467(7) 0.0251(4) Uani 1 1 d .
H8A H 0.0357 0.3777 -0.0121 0.038 Uiso 1 1 calc R
H8B H 0.2799 0.3784 -0.0415 0.038 Uiso 1 1 calc R
H8C H 0.2049 0.4597 0.0043 0.038 Uiso 1 1 calc R
C9 C 0.0813(3) 0.23846(12) 0.19270(7) 0.0248(4) Uani 1 1 d .
H9A H 0.1423 0.2058 0.2286 0.037 Uiso 1 1 calc R
H9B H -0.0590 0.2093 0.1803 0.037 Uiso 1 1 calc R
H9C H 0.0544 0.3035 0.2034 0.037 Uiso 1 1 calc R
H1 H 0.521(2) 0.4217(12) 0.0867(7) 0.024(4) Uiso 1 1 d .
H2 H 0.009(2) 0.2630(10) 0.0697(6) 0.016(4) Uiso 1 1 d .
H3 H 0.399(2) -0.0340(11) 0.1649(6) 0.026(5) Uiso 1 1 d .
H4 H 0.566(2) -0.0090(11) 0.1115(7) 0.023(5) Uiso 1 1 d .
H5 H 0.612(2) 0.3544(11) 0.0301(7) 0.027(4) 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
C7 O1 O2 105.92(10)
C1 O2 O1 106.21(10)
C2 O3 C3 115.94(12)
O2 C1 C5 109.51(13)
O2 C1 C2 112.10(12)
C5 C1 C2 111.16(13)
O2 C1 C9 104.03(12)
C5 C1 C9 112.09(13)
C2 C1 C9 107.76(14)
O4 C2 O3 123.85(16)
O4 C2 C1 122.90(14)
O3 C2 C1 113.16(14)
O3 C3 C4 106.74(13)
O3 C3 H3 109.2(9)
C4 C3 H3 112.5(9)
O3 C3 H4 109.2(9)
C4 C3 H4 112.5(8)
H3 C3 H4 106.6(12)
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C6 C5 C1 122.00(14)
C6 C5 H2 121.0(9)
C1 C5 H2 117.0(9)
C5 C6 C8 125.11(14)
C5 C6 C7 119.05(15)
C8 C6 C7 115.81(14)
O1 C7 C6 111.78(13)
O1 C7 H1 111.4(9)
C6 C7 H1 109.1(8)
O1 C7 H5 105.3(9)
C6 C7 H5 110.0(8)
H1 C7 H5 109.2(12)
C6 C8 H8A 109.5
C6 C8 H8B 109.5
H8A C8 H8B 109.5
C6 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C1 C9 H9A 109.5
C1 C9 H9B 109.5
H9A C9 H9B 109.5
C1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.4352(19)
O1 O2 1.4755(14)
O2 C1 1.4352(17)
O3 C2 1.3368(17)
O3 C3 1.4597(19)
O4 C2 1.2133(18)
C1 C5 1.507(2)
C1 C2 1.522(2)
C1 C9 1.529(2)
C3 C4 1.503(2)
C3 H3 0.993(15)
C3 H4 0.967(15)
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
C5 C6 1.325(2)
C5 H2 0.958(14)
C6 C8 1.495(2)
C6 C7 1.495(2)
C7 H1 1.017(16)
C7 H5 1.016(15)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 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
C7 O1 O2 C1 77.53(13)
O1 O2 C1 C5 -55.67(14)
O1 O2 C1 C2 68.18(14)
O1 O2 C1 C9 -175.66(11)
C3 O3 C2 O4 1.0(2)
C3 O3 C2 C1 177.62(13)
O2 C1 C2 O4 -160.03(14)
C5 C1 C2 O4 -37.1(2)
C9 C1 C2 O4 86.08(18)
O2 C1 C2 O3 23.34(17)
C5 C1 C2 O3 146.27(12)
C9 C1 C2 O3 -90.54(14)
C2 O3 C3 C4 -177.81(12)
O2 C1 C5 C6 16.4(2)
C2 C1 C5 C6 -108.01(18)
C9 C1 C5 C6 131.32(16)
C1 C5 C6 C8 -173.33(15)
C1 C5 C6 C7 4.8(2)
O2 O1 C7 C6 -54.79(17)
C5 C6 C7 O1 15.5(2)
C8 C6 C7 O1 -166.20(14)
