#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/91/2229141.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_2229141
loop_
_publ_author_name
'Zeng, Wu-Lan'
_publ_section_title
;
 2,2-Dimethyl-5-[(5-methylfuran-2-yl)methylidene]-1,3-dioxane-4,6-dione
;
_journal_coeditor_code           LH5196
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o478
_journal_paper_doi               10.1107/S1600536811002285
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C12 H12 O5'
_chemical_formula_moiety         'C12 H12 O5'
_chemical_formula_sum            'C12 H12 O5'
_chemical_formula_weight         236.22
_chemical_name_systematic
;
2,2-dimethyl-5-[(5-methylfuran-2-yl)methylidene]-1,3-dioxane-4,6-dione
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                92.71(3)
_cell_angle_beta                 105.99(3)
_cell_angle_gamma                91.67(3)
_cell_formula_units_Z            4
_cell_length_a                   8.9590(18)
_cell_length_b                   10.038(2)
_cell_length_c                   13.616(3)
_cell_measurement_reflns_used    3333
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.05
_cell_volume                     1174.7(5)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0243
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11592
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.302
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0444
_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)+(0.0907P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1563
_reflns_number_gt                3333
_reflns_number_total             5336
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5196.cif
_cod_data_source_block           I
_cod_original_cell_volume        1174.7(4)
_cod_database_code               2229141
_cod_database_fobs_code          2229141
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_disorder_assembly
_atom_site_disorder_group
O O2B 0.11969(13) 0.55646(11) 0.62210(9) 0.0618(3) Uani d . 1 . .
O O5B 0.45369(14) 1.05664(10) 0.82774(9) 0.0563(3) Uani d . 1 . .
O O1B 0.34137(15) 0.48325(11) 0.74003(9) 0.0645(3) Uani d . 1 . .
C C5B 0.29935(18) 0.71777(15) 0.73236(11) 0.0467(4) Uani d . 1 . .
O O3B 0.06239(14) 0.76729(12) 0.61279(9) 0.0671(3) Uani d . 1 . .
O O4B 0.48827(17) 0.61623(12) 0.86197(9) 0.0749(4) Uani d . 1 . .
C C6B 0.3859(2) 0.60755(16) 0.78319(12) 0.0536(4) Uani d . 1 . .
C C7B 0.33715(18) 0.84921(15) 0.75839(11) 0.0485(4) Uani d . 1 . .
H H7BA 0.2651 0.9054 0.7206 0.058 Uiso calc R 1 . .
C C4B 0.15441(19) 0.68642(16) 0.65155(12) 0.0522(4) Uani d . 1 . .
C C8B 0.46201(19) 0.91860(14) 0.83032(11) 0.0481(4) Uani d . 1 . .
C C9B 0.5954(2) 0.89135(17) 0.90245(12) 0.0564(4) Uani d . 1 . .
H H9BA 0.6302 0.8070 0.9202 0.068 Uiso calc R 1 . .
C C3B 0.2442(2) 0.46641(16) 0.63735(13) 0.0573(4) Uani d . 1 . .
C C11B 0.5813(2) 1.11096(17) 0.89765(13) 0.0569(4) Uani d . 1 . .
C C10B 0.6699(2) 1.01280(18) 0.94451(14) 0.0622(4) Uani d . 1 . .
H H10A 0.7635 1.0245 0.9955 0.075 Uiso calc R 1 . .
C C1B 0.1707(3) 0.32824(18) 0.62731(17) 0.0801(6) Uani d . 1 . .
H H1BA 0.1141 0.3201 0.6774 0.120 Uiso calc R 1 . .
H H1BB 0.2501 0.2640 0.6381 0.120 Uiso calc R 1 . .
H H1BC 0.1008 0.3123 0.5600 0.120 Uiso calc R 1 . .
C C2B 0.3372(3) 0.4908(2) 0.56325(16) 0.0780(6) Uani d . 1 . .
H H2BA 0.3813 0.5805 0.5749 0.117 Uiso calc R 1 . .
H H2BB 0.2708 0.4787 0.4946 0.117 Uiso calc R 1 . .
H H2BC 0.4191 0.4290 0.5728 0.117 Uiso calc R 1 . .
C C12B 0.5961(3) 1.25844(18) 0.90908(17) 0.0785(6) Uani d . 1 . .
H H12A 0.5088 1.2952 0.8619 0.118 Uiso calc R 1 . .
H H12B 0.6903 1.2885 0.8950 0.118 Uiso calc R 1 . .
H H12C 0.5986 1.2874 0.9778 0.118 Uiso calc R 1 . .
O O5A 0.07339(13) 0.59957(9) 0.88357(8) 0.0527(3) Uani d . 1 . .
O O2A -0.36509(13) 0.95250(10) 0.63621(9) 0.0573(3) Uani d . 1 . .
O O3A -0.35857(14) 0.73997(11) 0.66614(9) 0.0617(3) Uani d . 1 . .
C C5A -0.14448(18) 0.87879(13) 0.76199(11) 0.0447(3) Uani d . 1 . .
O O1A -0.17387(16) 1.11015(10) 0.72684(10) 0.0698(4) Uani d . 1 . .
C C8A -0.05825(18) 0.64850(14) 0.81836(11) 0.0447(3) Uani d . 1 . .
C C7A -0.05103(18) 0.78842(14) 0.81679(12) 0.0468(4) Uani d . 1 . .
H H7AA 0.0371 0.8277 0.8635 0.056 Uiso calc R 1 . .
C C4A -0.29180(18) 0.84726(14) 0.68578(11) 0.0461(4) Uani d . 1 . .
C C6A -0.0910(2) 1.01900(15) 0.78701(14) 0.0596(4) Uani d . 1 . .
O O4A 0.01460(18) 1.05984(12) 0.85763(12) 0.0924(5) Uani d . 1 . .
C C11A 0.0546(2) 0.46486(14) 0.87915(13) 0.0529(4) Uani d . 1 . .
C C9A -0.1573(2) 0.54271(14) 0.77519(13) 0.0556(4) Uani d . 1 . .
H H9AA -0.2548 0.5464 0.7287 0.067 Uiso calc R 1 . .
C C3A -0.2727(2) 1.06729(15) 0.62802(13) 0.0592(4) Uani d . 1 . .
C C10A -0.0843(2) 0.42757(15) 0.81423(14) 0.0614(5) Uani d . 1 . .
H H10B -0.1249 0.3404 0.7981 0.074 Uiso calc R 1 . .
C C2A -0.3843(3) 1.17833(18) 0.59790(17) 0.0892(7) Uani d . 1 . .
H H2AA -0.4385 1.1928 0.6490 0.134 Uiso calc R 1 . .
H H2AB -0.4578 1.1538 0.5332 0.134 Uiso calc R 1 . .
H H2AC -0.3273 1.2588 0.5924 0.134 Uiso calc R 1 . .
C C12A 0.1835(2) 0.39080(17) 0.94262(15) 0.0713(5) Uani d . 1 . .
H H12D 0.1569 0.2968 0.9333 0.107 Uiso calc R 1 . .
H H12E 0.2009 0.4190 1.0134 0.107 Uiso calc R 1 . .
H H12F 0.2763 0.4085 0.9223 0.107 Uiso calc R 1 . .
C C1A -0.1792(3) 1.0368(2) 0.55522(18) 0.0901(7) Uani d . 1 . .
H H1AA -0.1115 0.9659 0.5798 0.135 Uiso calc R 1 . .
H H1AB -0.1182 1.1149 0.5499 0.135 Uiso calc R 1 . .
H H1AC -0.2475 1.0099 0.4891 0.135 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4B O2B C3B . . 118.43(13) ?
C11B O5B C8B . . 107.37(13) ?
C6B O1B C3B . . 119.91(13) ?
C7B C5B C6B . . 124.95(15) ?
C7B C5B C4B . . 116.48(14) ?
C6B C5B C4B . . 118.43(15) ?
O4B C6B O1B . . 116.99(15) ?
O4B C6B C5B . . 126.11(16) ?
O1B C6B C5B . . 116.81(14) ?
C5B C7B C8B . . 133.72(14) ?
C5B C7B H7BA . . 113.1 ?
C8B C7B H7BA . . 113.1 ?
O3B C4B O2B . . 118.18(16) ?
O3B C4B C5B . . 124.96(16) ?
O2B C4B C5B . . 116.81(14) ?
C9B C8B O5B . . 107.91(15) ?
C9B C8B C7B . . 138.86(15) ?
O5B C8B C7B . . 113.20(13) ?
C8B C9B C10B . . 107.48(16) ?
C8B C9B H9BA . . 126.3 ?
C10B C9B H9BA . . 126.3 ?
O1B C3B O2B . . 110.13(13) ?
O1B C3B C2B . . 110.27(16) ?
O2B C3B C2B . . 109.85(15) ?
O1B C3B C1B . . 105.73(14) ?
O2B C3B C1B . . 106.35(16) ?
C2B C3B C1B . . 114.36(16) ?
O5B C11B C10B . . 109.69(15) ?
O5B C11B C12B . . 116.80(16) ?
C10B C11B C12B . . 133.51(18) ?
C11B C10B C9B . . 107.55(17) ?
C11B C10B H10A . . 126.2 ?
C9B C10B H10A . . 126.2 ?
C3B C1B H1BA . . 109.5 ?
C3B C1B H1BB . . 109.5 ?
H1BA C1B H1BB . . 109.5 ?
C3B C1B H1BC . . 109.5 ?
H1BA C1B H1BC . . 109.5 ?
H1BB C1B H1BC . . 109.5 ?
C3B C2B H2BA . . 109.5 ?
C3B C2B H2BB . . 109.5 ?
H2BA C2B H2BB . . 109.5 ?
C3B C2B H2BC . . 109.5 ?
H2BA C2B H2BC . . 109.5 ?
H2BB C2B H2BC . . 109.5 ?
C11B C12B H12A . . 109.5 ?
C11B C12B H12B . . 109.5 ?
H12A C12B H12B . . 109.5 ?
C11B C12B H12C . . 109.5 ?
H12A C12B H12C . . 109.5 ?
H12B C12B H12C . . 109.5 ?
C11A O5A C8A . . 107.77(13) ?
C4A O2A C3A . . 118.26(13) ?
C7A C5A C4A . . 125.38(14) ?
C7A C5A C6A . . 115.42(15) ?
C4A C5A C6A . . 119.16(13) ?
C6A O1A C3A . . 119.26(12) ?
C9A C8A O5A . . 108.02(13) ?
C9A C8A C7A . . 139.38(15) ?
O5A C8A C7A . . 112.60(13) ?
C5A C7A C8A . . 134.05(16) ?
C5A C7A H7AA . . 113.0 ?
C8A C7A H7AA . . 113.0 ?
O3A C4A O2A . . 117.16(15) ?
O3A C4A C5A . . 126.53(14) ?
O2A C4A C5A . . 116.19(13) ?
O4A C6A O1A . . 117.49(15) ?
O4A C6A C5A . . 125.89(14) ?
O1A C6A C5A . . 116.55(15) ?
C10A C11A O5A . . 109.20(14) ?
C10A C11A C12A . . 133.71(15) ?
O5A C11A C12A . . 117.09(16) ?
C8A C9A C10A . . 106.92(16) ?
C8A C9A H9AA . . 126.5 ?
C10A C9A H9AA . . 126.5 ?
O2A C3A O1A . . 109.72(13) ?
O2A C3A C1A . . 110.21(15) ?
O1A C3A C1A . . 110.72(17) ?
O2A C3A C2A . . 106.18(16) ?
O1A C3A C2A . . 105.14(14) ?
C1A C3A C2A . . 114.63(17) ?
C11A C10A C9A . . 108.08(15) ?
C11A C10A H10B . . 126.0 ?
C9A C10A H10B . . 126.0 ?
C3A C2A H2AA . . 109.5 ?
C3A C2A H2AB . . 109.5 ?
H2AA C2A H2AB . . 109.5 ?
C3A C2A H2AC . . 109.5 ?
H2AA C2A H2AC . . 109.5 ?
H2AB C2A H2AC . . 109.5 ?
C11A C12A H12D . . 109.5 ?
C11A C12A H12E . . 109.5 ?
H12D C12A H12E . . 109.5 ?
C11A C12A H12F . . 109.5 ?
H12D C12A H12F . . 109.5 ?
H12E C12A H12F . . 109.5 ?
C3A C1A H1AA . . 109.5 ?
C3A C1A H1AB . . 109.5 ?
H1AA C1A H1AB . . 109.5 ?
C3A C1A H1AC . . 109.5 ?
H1AA C1A H1AC . . 109.5 ?
H1AB C1A H1AC . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O2B C4B . 1.348(2) ?
O2B C3B . 1.433(2) ?
O5B C11B . 1.351(2) ?
O5B C8B . 1.3914(17) ?
O1B C6B . 1.354(2) ?
O1B C3B . 1.428(2) ?
C5B C7B . 1.358(2) ?
C5B C6B . 1.460(2) ?
C5B C4B . 1.467(2) ?
O3B C4B . 1.2070(19) ?
O4B C6B . 1.202(2) ?
C7B C8B . 1.408(2) ?
C7B H7BA . 0.9300 ?
C8B C9B . 1.366(2) ?
C9B C10B . 1.391(2) ?
C9B H9BA . 0.9300 ?
C3B C2B . 1.499(3) ?
C3B C1B . 1.502(2) ?
C11B C10B . 1.354(2) ?
C11B C12B . 1.480(2) ?
C10B H10A . 0.9300 ?
C1B H1BA . 0.9600 ?
C1B H1BB . 0.9600 ?
C1B H1BC . 0.9600 ?
C2B H2BA . 0.9600 ?
C2B H2BB . 0.9600 ?
C2B H2BC . 0.9600 ?
C12B H12A . 0.9600 ?
C12B H12B . 0.9600 ?
C12B H12C . 0.9600 ?
O5A C11A . 1.3542(17) ?
O5A C8A . 1.3851(18) ?
O2A C4A . 1.3662(18) ?
O2A C3A . 1.425(2) ?
O3A C4A . 1.1985(19) ?
C5A C7A . 1.358(2) ?
C5A C4A . 1.452(2) ?
C5A C6A . 1.467(2) ?
O1A C6A . 1.3545(19) ?
O1A C3A . 1.431(2) ?
C8A C9A . 1.364(2) ?
C8A C7A . 1.4056(19) ?
C7A H7AA . 0.9300 ?
C6A O4A . 1.194(2) ?
C11A C10A . 1.344(3) ?
C11A C12A . 1.481(2) ?
C9A C10A . 1.399(2) ?
C9A H9AA . 0.9300 ?
C3A C1A . 1.491(3) ?
C3A C2A . 1.514(2) ?
C10A H10B . 0.9300 ?
C2A H2AA . 0.9600 ?
C2A H2AB . 0.9600 ?
C2A H2AC . 0.9600 ?
C12A H12D . 0.9600 ?
C12A H12E . 0.9600 ?
C12A H12F . 0.9600 ?
C1A H1AA . 0.9600 ?
C1A H1AB . 0.9600 ?
C1A H1AC . 0.9600 ?
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
_geom_hbond_publ_flag
C1B H1BC O3B 2_566 0.96 2.48 3.434(3) 170 y
C10B H10A O4A 2_677 0.93 2.60 3.448(3) 153 y
C10A H10B O1A 1_545 0.93 2.44 3.343(2) 163 y
C2A H2AB O2A 2_476 0.96 2.57 3.524(3) 170 y
C1A H1AA O3B . 0.96 2.55 3.496(3) 170 y
