#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/74/2237472.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2237472
loop_
_publ_author_name
'Beginn, Uwe'
'Frosinn, Martin'
'Reichelt, Martin'
'Reuter, Hans'
_publ_section_title
;
 3-Methylideneoxolane-2,5-dione
;
_journal_coeditor_code           GG2110
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o321
_journal_paper_doi               10.1107/S1600536813002924
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C5 H4 O3'
_chemical_formula_moiety         'C5 H4 O3'
_chemical_formula_sum            'C5 H4 O3'
_chemical_formula_weight         112.08
_chemical_melting_point          340.05
_chemical_name_common
;
3-Methylenedihydrofuran-2,5-dione
;
_chemical_name_systematic
;
3-Methylideneoxolane-2,5-dione
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   5.4854(3)
_cell_length_b                   7.3498(5)
_cell_length_c                   12.1871(7)
_cell_measurement_reflns_used    6479
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.03
_cell_measurement_theta_min      3.24
_cell_volume                     491.34(5)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2006) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω 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  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18134
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         3.24
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_correction_T_min  0.9662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.144
_refine_ls_extinction_coef       0.037(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0258
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0343P)²+0.0728P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0648
_reflns_number_gt                639
_reflns_number_total             716
_reflns_threshold_expression     I>2σ(I)
_iucr_refine_instructions_details
;
TITL I in P2(1)2(1)2(1)
CELL 0.71073 5.4854 7.3498 12.1871 90.000 90.000 90.000
ZERR 4.00 0.0003 0.0005 0.0007 0.000 0.000 0.000
LATT -1
SYMM x+1/2, -y+1/2, -z
SYMM -x, y+1/2, -z+1/2
SYMM -x+1/2, -y, z+1/2
SFAC C  H  O
UNIT 20  16  12
OMIT -3 56
L.S. 4
MERG 4
REM ACTA
MPLA 4 O1 C2 C3 C4 C5 C6 O2 O5
MPLA 3 O1 C5 C4
BOND $H
HTAB
FMAP 2
PLAN 1
SIZE 0.072 0.09 0.27
TEMP -173
WGHT    0.034300    0.072800
EXTI    0.037451
FVAR       0.48786
MOLE 1
O1    3    1.004109    0.790210    0.613761    11.00000    0.01635    0.02154 =
         0.01850   -0.00161    0.00026    0.00359
C2    1    0.896723    0.911257    0.540148    11.00000    0.01654    0.01552 =
         0.01682   -0.00291   -0.00293   -0.00179
O2    3    0.993901    0.943614    0.454734    11.00000    0.02147    0.02794 =
         0.01765   -0.00179    0.00381   -0.00328
C3    1    0.665556    0.977512    0.588260    11.00000    0.01426    0.01572 =
         0.01628   -0.00403   -0.00035   -0.00214
C4    1    0.639273    0.889369    0.698561    11.00000    0.01716    0.01764 =
         0.01707   -0.00059    0.00047    0.00005
AFIX  23
H4A   2    0.487259    0.817110    0.702840    11.00000   -1.20000
H4B   2    0.638999    0.981356    0.757902    11.00000   -1.20000
AFIX   0
C5    1    0.859968    0.769078    0.705853    11.00000    0.02059    0.02115 =
         0.01659   -0.00361   -0.00117    0.00064
O5    3    0.919986    0.666060    0.776591    11.00000    0.03351    0.03302 =
         0.02312    0.00765   -0.00132    0.01226
C6    1    0.520215    1.091227    0.535986    11.00000    0.01773    0.01875 =
         0.02455    0.00113   -0.00093   -0.00052
AFIX  93
H6A   2    0.562625    1.133493    0.464836    11.00000   -1.20000
H6B   2    0.373131    1.130859    0.569488    11.00000   -1.20000
HKLF 4 1 1 0 0 0 1 0 0 0 1
;
_cod_data_source_file            gg2110.cif
_cod_data_source_block           I
_cod_database_code               2237472
_cod_database_fobs_code          2237472
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O1 1.00411(19) 0.79021(13) 0.61376(8) 0.0188(3) Uani d . 1 1
C C2 0.8967(3) 0.9113(2) 0.54015(12) 0.0163(3) Uani d . 1 1
O O2 0.99390(19) 0.94361(14) 0.45473(8) 0.0224(3) Uani d . 1 1
C C3 0.6656(3) 0.9775(2) 0.58826(12) 0.0154(3) Uani d . 1 1
C C4 0.6393(3) 0.8894(2) 0.69856(12) 0.0173(3) Uani d . 1 1
H H4A 0.4873 0.8171 0.7028 0.021 Uiso calc R 1 1
H H4B 0.6390 0.9814 0.7579 0.021 Uiso calc R 1 1
C C5 0.8600(3) 0.7691(2) 0.70585(12) 0.0194(3) Uani d . 1 1
O O5 0.9200(2) 0.66606(17) 0.77659(9) 0.0299(3) Uani d . 1 1
C C6 0.5202(3) 1.0912(2) 0.53599(12) 0.0203(3) Uani d . 1 1
H H6A 0.5626 1.1335 0.4648 0.024 Uiso calc R 1 1
H H6B 0.3731 1.1309 0.5695 0.024 Uiso calc R 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0164(5) 0.0215(5) 0.0185(5) 0.0036(5) 0.0003(5) -0.0016(4)
C2 0.0165(7) 0.0155(7) 0.0168(7) -0.0018(6) -0.0029(6) -0.0029(6)
O2 0.0215(6) 0.0279(6) 0.0176(5) -0.0033(5) 0.0038(6) -0.0018(4)
C3 0.0143(7) 0.0157(7) 0.0163(6) -0.0021(6) -0.0004(6) -0.0040(6)
C4 0.0172(7) 0.0176(7) 0.0171(6) 0.0001(6) 0.0005(6) -0.0006(6)
C5 0.0206(8) 0.0212(8) 0.0166(7) 0.0006(7) -0.0012(7) -0.0036(6)
O5 0.0335(7) 0.0330(7) 0.0231(6) 0.0123(6) -0.0013(5) 0.0077(5)
C6 0.0177(7) 0.0187(7) 0.0245(7) -0.0005(7) -0.0009(7) 0.0011(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 0.0000 '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_publ_flag
C2 O1 C5 110.65(11) yes
O1 C2 O2 119.98(13) yes
O2 C2 C3 131.52(14) yes
O1 C2 C3 108.49(12) yes
C2 C3 C6 122.35(13) yes
C4 C3 C6 130.45(14) yes
C2 C3 C4 107.19(13) yes
C3 C4 C5 103.29(13) yes
O1 C5 O5 120.01(14) yes
O5 C5 C4 129.68(15) yes
O1 C5 C4 110.31(12) yes
C3 C4 H4A 111.1 no
C5 C4 H4A 111.1 no
C3 C4 H4B 111.1 no
C5 C4 H4B 111.1 no
H4A C4 H4B 109.1 no
C3 C6 H6A 120.0 no
C3 C6 H6B 120.0 no
H6A C6 H6B 120.0 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C5 1.382(2) no
O1 C2 1.394(2) no
C2 O2 1.193(2) no
C2 C3 1.479(2) no
C3 C6 1.319(2) no
C3 C4 1.499(2) no
C4 C5 1.502(2) no
C4 H4A 0.9900 no
C4 H4B 0.9900 no
C5 O5 1.194(2) no
C6 H6A 0.9500 no
C6 H6B 0.9500 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C6 H6A O5 4_674 0.95 2.73 3.645(2) 162
C6 H6B O5 3_656 0.95 2.48 3.369(2) 155
C4 H4B O2 4_675 0.99 2.57 3.433(2) 146
C4 H4A O2 2_466 0.99 2.71 3.181(2) 109
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
O1 C2 C3 C4 0.65(15)
C2 C3 C4 C5 -1.86(15)
C3 C4 C5 O1 2.54(16)
C4 C5 O1 C2 -2.28(16)
C5 O1 C2 C3 1.00(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 67661
