#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/79/2017933.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_2017933
loop_
_publ_author_name
'Strübe, Frank'
'Mattay, Jochen'
'Neumann, Beate'
'Stammler, Hans-Georg'
_publ_section_title
;
 Rotationally-hindered furyl fulgides
;
_journal_coeditor_code           EG3067
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o33
_journal_page_last               o36
_journal_paper_doi               10.1107/S0108270110049401
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C19 H18 O5'
_chemical_formula_moiety         'C19 H18 O5'
_chemical_formula_sum            'C19 H18 O5'
_chemical_formula_weight         326.33
_chemical_name_systematic
;
3-isopropylidene-4-[(Z)-1-(5-methoxy-2-methyl-1-benzofuran-3-
yl)ethylidene]tetrahydrofuran-2,5-dione
;
_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                 115.8482(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.5923(4)
_cell_length_b                   8.61400(10)
_cell_length_c                   15.3550(2)
_cell_measurement_reflns_used    31599
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     3165.41(8)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Bruker, 2004)'
_computing_data_reduction
'SCALEPACK and DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_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  0.033
_diffrn_reflns_av_sigmaI/netI    0.0150
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            54136
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.9709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(DENZO and SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0339
_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)+(0.0494P)²+1.6756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0911
_reflns_number_gt                3205
_reflns_number_total             3606
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            eg3067.cif
_cod_data_source_block           III-Z
_cod_original_cell_volume        3165.41(7)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2017933
_cod_database_fobs_code          2017933
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_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 O1 0.43332(3) 0.28489(9) 0.50657(5) 0.02243(18) Uani d . 1 . .
O O2 0.36292(3) 0.28865(9) 0.54967(5) 0.02397(18) Uani d . 1 . .
O O3 0.49219(3) 0.32877(9) 0.43999(6) 0.02698(19) Uani d . 1 . .
O O4 0.25671(3) 0.56512(8) 0.58670(5) 0.01936(17) Uani d . 1 . .
O O5 0.41157(3) 0.96371(9) 0.84152(5) 0.02463(18) Uani d . 1 . .
C C1 0.38619(4) 0.35342(12) 0.50851(7) 0.0191(2) Uani d . 1 . .
C C2 0.37786(4) 0.50603(12) 0.45912(7) 0.0168(2) Uani d . 1 . .
C C3 0.41158(4) 0.49955(12) 0.40447(7) 0.0176(2) Uani d . 1 . .
C C4 0.45132(4) 0.37032(12) 0.44801(7) 0.0208(2) Uani d . 1 . .
C C5 0.40443(4) 0.57194(12) 0.32176(7) 0.0183(2) Uani d . 1 . .
C C6 0.44539(4) 0.55653(13) 0.27886(8) 0.0235(2) Uani d . 1 . .
H H6A 0.4339 0.6241 0.2221 0.035 Uiso calc PR 0.50 . .
H H6B 0.4462 0.4485 0.2595 0.035 Uiso calc PR 0.50 . .
H H6C 0.4827 0.5870 0.3271 0.035 Uiso calc PR 0.50 . .
H H6D 0.4747 0.4823 0.3170 0.035 Uiso calc PR 0.50 . .
H H6E 0.4623 0.6579 0.2796 0.035 Uiso calc PR 0.50 . .
H H6F 0.4259 0.5194 0.2120 0.035 Uiso calc PR 0.50 . .
C C7 0.35396(4) 0.66927(12) 0.26469(7) 0.0202(2) Uani d . 1 . .
H H7A 0.3244 0.6448 0.2844 0.030 Uiso calc R 1 . .
H H7B 0.3407 0.6473 0.1956 0.030 Uiso calc R 1 . .
H H7C 0.3638 0.7794 0.2768 0.030 Uiso calc R 1 . .
C C8 0.35857(4) 0.63356(12) 0.48736(7) 0.0168(2) Uani d . 1 . .
C C9 0.37121(4) 0.79532(11) 0.46521(7) 0.0193(2) Uani d . 1 . .
H H9A 0.4053 0.7938 0.4556 0.029 Uiso calc R 1 . .
H H9B 0.3766 0.8643 0.5194 0.029 Uiso calc R 1 . .
H H9C 0.3400 0.8332 0.4063 0.029 Uiso calc R 1 . .
C C10 0.32634(4) 0.62310(11) 0.54440(7) 0.0170(2) Uani d . 1 . .
C C11 0.33636(4) 0.70789(11) 0.63227(7) 0.0175(2) Uani d . 1 . .
C C12 0.37859(4) 0.80759(11) 0.69452(7) 0.0187(2) Uani d . 1 . .
H H12 0.4094 0.8348 0.6819 0.022 Uiso calc R 1 . .
C C13 0.37377(4) 0.86504(12) 0.77526(7) 0.0201(2) Uani d . 1 . .
C C14 0.32842(4) 0.82390(12) 0.79484(7) 0.0217(2) Uani d . 1 . .
H H14 0.3259 0.8665 0.8498 0.026 Uiso calc R 1 . .
C C15 0.28751(4) 0.72235(12) 0.73519(7) 0.0209(2) Uani d . 1 . .
H H15 0.2573 0.6921 0.7488 0.025 Uiso calc R 1 . .
C C16 0.29269(4) 0.66695(12) 0.65469(7) 0.0184(2) Uani d . 1 . .
C C17 0.27817(4) 0.54146(12) 0.52062(7) 0.0181(2) Uani d . 1 . .
C C18 0.24448(4) 0.44074(12) 0.43702(7) 0.0211(2) Uani d . 1 . .
H H18A 0.2461 0.4811 0.3786 0.032 Uiso calc R 1 . .
H H18B 0.2056 0.4397 0.4276 0.032 Uiso calc R 1 . .
H H18C 0.2595 0.3349 0.4496 0.032 Uiso calc R 1 . .
C C19 0.46033(5) 1.00277(14) 0.82939(9) 0.0290(3) Uani d . 1 . .
H H19A 0.4809 0.9078 0.8303 0.043 Uiso calc R 1 . .
H H19B 0.4843 1.0713 0.8822 0.043 Uiso calc R 1 . .
H H19C 0.4493 1.0560 0.7673 0.043 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
C1 O1 C4 . . 110.68(8) ?
C17 O4 C16 . . 106.13(8) ?
C13 O5 C19 . . 117.60(8) ?
O2 C1 O1 . . 119.28(9) ?
O2 C1 C2 . . 133.27(9) ?
O1 C1 C2 . . 107.36(8) ?
C8 C2 C3 . . 128.33(9) ?
C8 C2 C1 . . 123.01(9) ?
C3 C2 C1 . . 105.38(8) ?
C5 C3 C2 . . 130.30(9) ?
C5 C3 C4 . . 123.51(9) ?
C2 C3 C4 . . 105.29(8) ?
O3 C4 O1 . . 119.22(10) ?
O3 C4 C3 . . 132.73(10) ?
O1 C4 C3 . . 108.03(8) ?
C3 C5 C7 . . 122.05(9) ?
C3 C5 C6 . . 122.58(9) ?
C7 C5 C6 . . 115.34(9) ?
C5 C6 H6A . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C5 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C5 C6 H6D . . 109.5 ?
H6A C6 H6D . . 141.1 ?
H6B C6 H6D . . 56.3 ?
H6C C6 H6D . . 56.3 ?
C5 C6 H6E . . 109.5 ?
H6A C6 H6E . . 56.3 ?
H6B C6 H6E . . 141.1 ?
H6C C6 H6E . . 56.3 ?
H6D C6 H6E . . 109.5 ?
C5 C6 H6F . . 109.5 ?
H6A C6 H6F . . 56.3 ?
H6B C6 H6F . . 56.3 ?
H6C C6 H6F . . 141.1 ?
H6D C6 H6F . . 109.5 ?
H6E C6 H6F . . 109.5 ?
C5 C7 H7A . . 109.5 ?
C5 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C5 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C2 C8 C10 . . 122.59(9) ?
C2 C8 C9 . . 121.50(9) ?
C10 C8 C9 . . 115.86(8) ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C17 C10 C11 . . 106.16(8) ?
C17 C10 C8 . . 126.51(9) ?
C11 C10 C8 . . 127.12(9) ?
C16 C11 C12 . . 119.44(9) ?
C16 C11 C10 . . 105.50(9) ?
C12 C11 C10 . . 135.00(9) ?
C13 C12 C11 . . 117.79(9) ?
C13 C12 H12 . . 121.1 ?
C11 C12 H12 . . 121.1 ?
O5 C13 C12 . . 124.02(10) ?
O5 C13 C14 . . 114.63(9) ?
C12 C13 C14 . . 121.36(10) ?
C15 C14 C13 . . 121.08(9) ?
C15 C14 H14 . . 119.5 ?
C13 C14 H14 . . 119.5 ?
C14 C15 C16 . . 116.87(9) ?
C14 C15 H15 . . 121.6 ?
C16 C15 H15 . . 121.6 ?
O4 C16 C15 . . 125.99(9) ?
O4 C16 C11 . . 110.59(8) ?
C15 C16 C11 . . 123.42(10) ?
C10 C17 O4 . . 111.62(9) ?
C10 C17 C18 . . 132.50(9) ?
O4 C17 C18 . . 115.82(9) ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
O5 C19 H19A . . 109.5 ?
O5 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O5 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 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
O1 C1 . 1.3974(12) ?
O1 C4 . 1.3979(13) ?
O2 C1 . 1.1977(13) ?
O3 C4 . 1.2006(13) ?
O4 C17 . 1.3791(12) ?
O4 C16 . 1.3797(12) ?
O5 C13 . 1.3698(13) ?
O5 C19 . 1.4282(14) ?
C1 C2 . 1.4853(14) ?
C2 C8 . 1.3609(14) ?
C2 C3 . 1.4722(13) ?
C3 C5 . 1.3517(14) ?
C3 C4 . 1.4788(14) ?
C5 C7 . 1.4989(14) ?
C5 C6 . 1.5047(13) ?
C5 C17 . 5.4409(14) ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 0.9800 ?
C6 H6D . 0.9800 ?
C6 H6E . 0.9800 ?
C6 H6F . 0.9800 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 C10 . 1.4712(13) ?
C8 C9 . 1.5066(13) ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 C17 . 1.3641(14) ?
C10 C11 . 1.4530(13) ?
C11 C16 . 1.3929(14) ?
C11 C12 . 1.4059(14) ?
C12 C13 . 1.3918(14) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.4093(15) ?
C14 C15 . 1.3852(16) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.3868(14) ?
C15 H15 . 0.9500 ?
C17 C18 . 1.4835(14) ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 C8 C10 C17 . . . . -55.72(15) ?
C3 C2 C8 C10 . . . . -178.29(9) ?
C8 C2 C3 C5 . . . . -49.02(16) ?
C2 C8 C10 C11 . . . . 130.31(11) ?
C1 C2 C3 C5 . . . . 151.31(10) ?
