#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:53:49 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178410 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/31/4023167.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_4023167
loop_
_publ_author_name
'Yit Wooi Goh'
'Brett R. Pool'
'Jonathan M. White'
_publ_section_title
;
 Structural Studies on Cycloadducts of Furan, 2-Methoxyfuran,
 and 5-Trimethylsilylcyclopentadiene with Maleic Anhydride
 and N-Methylmaleimide
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              151
_journal_page_last               156
_journal_paper_doi               10.1021/jo7018575
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C9 H8 O5'
_chemical_formula_weight         196.15
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 117.184(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.166(6)
_cell_length_b                   5.3338(13)
_cell_length_c                   13.990(4)
_cell_measurement_reflns_used    876
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      24.43
_cell_measurement_theta_min      2.93
_cell_volume                     1670.4(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1003
_diffrn_reflns_av_sigmaI/netI    0.0909
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4185
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0000(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.907
_refine_ls_R_factor_all          0.0695
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.928
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0432P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1072
_reflns_number_gt                1032
_reflns_number_total             1476
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7018575-File001_09.cif
_cod_data_source_block           CMPD21
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      'C 2/c'
_cod_database_code               4023167
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.33423(10) 0.1049(4) 0.3414(2) 0.0273(6) Uani 1 1 d . . .
C2 C 0.34826(10) 0.3427(4) 0.30027(18) 0.0221(6) Uani 1 1 d . . .
H2 H 0.3408 0.4929 0.3326 0.027 Uiso 1 1 calc R . .
C3 C 0.41277(10) 0.3389(4) 0.30866(18) 0.0233(6) Uani 1 1 d . . .
C4 C 0.42102(11) 0.5903(4) 0.2672(2) 0.0267(6) Uani 1 1 d . . .
H4 H 0.4452 0.7217 0.3074 0.032 Uiso 1 1 calc R . .
C5 C 0.38702(10) 0.5851(4) 0.1623(2) 0.0265(6) Uani 1 1 d . . .
H5 H 0.3818 0.7128 0.1135 0.032 Uiso 1 1 calc R . .
C6 C 0.35838(10) 0.3288(4) 0.13771(19) 0.0253(6) Uani 1 1 d . . .
H6 H 0.3448 0.2703 0.0638 0.030 Uiso 1 1 calc R . .
C7 C 0.30953(10) 0.3327(4) 0.17763(18) 0.0229(6) Uani 1 1 d . . .
H7 H 0.2820 0.4747 0.1494 0.027 Uiso 1 1 calc R . .
C8 C 0.27832(10) 0.0849(4) 0.1574(2) 0.0274(6) Uani 1 1 d . . .
C9 C 0.51420(10) 0.2453(5) 0.4161(2) 0.0376(7) Uani 1 1 d . . .
H9A H 0.5146 0.1668 0.3547 0.056 Uiso 1 1 calc R . .
H9B H 0.5402 0.1554 0.4800 0.056 Uiso 1 1 calc R . .
H9C H 0.5278 0.4154 0.4215 0.056 Uiso 1 1 calc R . .
O1 O 0.35069(8) 0.0295(3) 0.43045(14) 0.0372(5) Uani 1 1 d . . .
O2 O 0.24473(8) -0.0138(3) 0.07608(15) 0.0409(5) Uani 1 1 d . . .
O3 O 0.40260(6) 0.1748(3) 0.21944(12) 0.0244(4) Uani 1 1 d . . .
O4 O 0.29482(7) -0.0415(3) 0.25497(13) 0.0302(4) Uani 1 1 d . . .
O5 O 0.45428(7) 0.2430(3) 0.40450(13) 0.0283(4) Uani 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O4 119.1(2) . . ?
O1 C1 C2 131.1(2) . . ?
O4 C1 C2 109.8(2) . . ?
C1 C2 C7 104.94(18) . . ?
C1 C2 C3 112.10(17) . . ?
C7 C2 C3 100.90(17) . . ?
C1 C2 H2 112.7 . . ?
C7 C2 H2 112.7 . . ?
C3 C2 H2 112.7 . . ?
O5 C3 O3 111.94(18) . . ?
O5 C3 C4 122.04(19) . . ?
O3 C3 C4 101.89(18) . . ?
O5 C3 C2 112.20(18) . . ?
O3 C3 C2 99.98(17) . . ?
C4 C3 C2 106.15(17) . . ?
C5 C4 C3 106.0(2) . . ?
C5 C4 H4 127.0 . . ?
C3 C4 H4 127.0 . . ?
C4 C5 C6 105.8(2) . . ?
C4 C5 H5 127.1 . . ?
C6 C5 H5 127.1 . . ?
O3 C6 C5 102.78(18) . . ?
O3 C6 C7 99.96(17) . . ?
C5 C6 C7 106.13(18) . . ?
O3 C6 H6 115.4 . . ?
C5 C6 H6 115.4 . . ?
C7 C6 H6 115.4 . . ?
C8 C7 C2 104.59(17) . . ?
C8 C7 C6 110.53(18) . . ?
C2 C7 C6 101.39(17) . . ?
C8 C7 H7 113.1 . . ?
C2 C7 H7 113.1 . . ?
C6 C7 H7 113.1 . . ?
O2 C8 O4 118.9(2) . . ?
O2 C8 C7 131.0(2) . . ?
O4 C8 C7 110.1(2) . . ?
O5 C9 H9A 109.5 . . ?
O5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 O3 C3 96.21(15) . . ?
C1 O4 C8 110.47(18) . . ?
C3 O5 C9 113.50(17) . . ?
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
C1 O1 1.189(3) . ?
C1 O4 1.400(3) . ?
C1 C2 1.500(3) . ?
C2 C7 1.539(3) . ?
C2 C3 1.573(3) . ?
C2 H2 0.9800 . ?
C3 O5 1.368(3) . ?
C3 O3 1.448(3) . ?
C3 C4 1.512(3) . ?
C4 C5 1.319(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.510(3) . ?
C5 H5 0.9300 . ?
C6 O3 1.434(3) . ?
C6 C7 1.566(3) . ?
C6 H6 0.9800 . ?
C7 C8 1.497(3) . ?
C7 H7 0.9800 . ?
C8 O2 1.186(3) . ?
C8 O4 1.404(3) . ?
C9 O5 1.441(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
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
O1 C1 C2 C7 -176.6(2) . . . . ?
O4 C1 C2 C7 3.4(2) . . . . ?
O1 C1 C2 C3 74.8(3) . . . . ?
O4 C1 C2 C3 -105.3(2) . . . . ?
C1 C2 C3 O5 -43.1(3) . . . . ?
C7 C2 C3 O5 -154.31(18) . . . . ?
C1 C2 C3 O3 75.7(2) . . . . ?
C7 C2 C3 O3 -35.53(18) . . . . ?
C1 C2 C3 C4 -178.73(19) . . . . ?
C7 C2 C3 C4 70.1(2) . . . . ?
O5 C3 C4 C5 157.6(2) . . . . ?
O3 C3 C4 C5 32.0(2) . . . . ?
C2 C3 C4 C5 -72.2(2) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
C4 C5 C6 O3 -30.6(2) . . . . ?
C4 C5 C6 C7 73.9(2) . . . . ?
C1 C2 C7 C8 -2.4(2) . . . . ?
C3 C2 C7 C8 114.21(18) . . . . ?
C1 C2 C7 C6 -117.37(18) . . . . ?
C3 C2 C7 C6 -0.75(19) . . . . ?
O3 C6 C7 C8 -73.2(2) . . . . ?
C5 C6 C7 C8 -179.75(19) . . . . ?
O3 C6 C7 C2 37.26(19) . . . . ?
C5 C6 C7 C2 -69.3(2) . . . . ?
C2 C7 C8 O2 -178.0(2) . . . . ?
C6 C7 C8 O2 -69.6(3) . . . . ?
C2 C7 C8 O4 0.7(2) . . . . ?
C6 C7 C8 O4 109.13(19) . . . . ?
C5 C6 O3 C3 48.28(19) . . . . ?
C7 C6 O3 C3 -60.93(18) . . . . ?
O5 C3 O3 C6 179.37(17) . . . . ?
C4 C3 O3 C6 -48.61(19) . . . . ?
C2 C3 O3 C6 60.39(18) . . . . ?
O1 C1 O4 C8 176.91(19) . . . . ?
C2 C1 O4 C8 -3.0(2) . . . . ?
O2 C8 O4 C1 -179.7(2) . . . . ?
C7 C8 O4 C1 1.4(2) . . . . ?
O3 C3 O5 C9 70.6(2) . . . . ?
C4 C3 O5 C9 -50.4(3) . . . . ?
C2 C3 O5 C9 -177.93(18) . . . . ?
