#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/32/2223264.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_2223264
loop_
_publ_author_name
'Bolte, Michael'
'Schwarz, Lothar'
'Hashmi, A. Stephen K.'
_publ_section_title
;
 Bis[5-(4-methoxybenzyl)furan-3-yl]methanone
;
_journal_coeditor_code           AT2869
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2325
_journal_paper_doi               10.1107/S1600536809034333
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C25 H22 O5'
_chemical_formula_moiety         'C25 H22 O5'
_chemical_formula_sum            'C25 H22 O5'
_chemical_formula_weight         402.43
_chemical_name_systematic
;
Bis[5-(4-methoxybenzyl)furan-3-yl]methanone
;
_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                 99.594(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   42.050(2)
_cell_length_b                   5.9183(2)
_cell_length_c                   8.3269(3)
_cell_measurement_reflns_used    5761
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      24.8
_cell_measurement_theta_min      5.2
_cell_volume                     2043.29(14)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device_type  'Siemens CCD three-circle'
_diffrn_measurement_method       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  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_h_min       -50
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8458
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.19
_diffrn_reflns_theta_min         1.96
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.233
_refine_ls_extinction_coef       0.0039(8)
_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   1.254
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1854
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.254
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0811
_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)+(0.0374P)²+9.4535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1888
_refine_ls_wR_factor_ref         0.1951
_reflns_number_gt                1506
_reflns_number_total             1854
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2869.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2223264
_cod_database_fobs_code          2223264
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
C C1 0.37264(9) 0.2789(7) 0.4374(5) 0.0332(9) Uani d . 1 . .
C C2 0.35544(9) 0.0841(7) 0.4534(5) 0.0385(10) Uani d . 1 . .
H H2 0.3643 -0.0267 0.5307 0.046 Uiso calc R 1 . .
C C3 0.32526(9) 0.0460(7) 0.3586(5) 0.0389(10) Uani d . 1 . .
H H3 0.3137 -0.0887 0.3716 0.047 Uiso calc R 1 . .
C C4 0.31251(9) 0.2064(7) 0.2458(5) 0.0328(9) Uani d . 1 . .
O O41 0.28319(6) 0.1887(5) 0.1431(4) 0.0422(8) Uani d . 1 . .
C C42 0.26472(10) -0.0101(9) 0.1577(6) 0.0534(13) Uani d . 1 . .
H H42A 0.2618 -0.0290 0.2712 0.080 Uiso calc R 1 . .
H H42B 0.2761 -0.1418 0.1237 0.080 Uiso calc R 1 . .
H H42C 0.2436 0.0038 0.0881 0.080 Uiso calc R 1 . .
C C5 0.32947(9) 0.4037(7) 0.2275(5) 0.0363(10) Uani d . 1 . .
H H5 0.3207 0.5142 0.1499 0.044 Uiso calc R 1 . .
C C6 0.35934(9) 0.4378(7) 0.3238(5) 0.0364(10) Uani d . 1 . .
H H6 0.3709 0.5729 0.3114 0.044 Uiso calc R 1 . .
C C7 0.40530(9) 0.3207(8) 0.5416(5) 0.0415(11) Uani d . 1 . .
H H7A 0.4047 0.4680 0.5974 0.050 Uiso calc R 1 . .
H H7B 0.4092 0.2022 0.6265 0.050 Uiso calc R 1 . .
C C11 0.43293(9) 0.3219(7) 0.4488(5) 0.0339(9) Uani d . 1 . .
C C12 0.45192(8) 0.4804(7) 0.4054(4) 0.0308(9) Uani d . 1 . .
H H12 0.4509 0.6373 0.4279 0.037 Uiso calc R 1 . .
C C13 0.47441(8) 0.3727(6) 0.3184(5) 0.0297(9) Uani d . 1 . .
C C31 0.5000 0.4907(9) 0.2500 0.0297(12) Uani d S 1 . .
O O32 0.5000 0.6987(7) 0.2500 0.0418(10) Uani d S 1 . .
C C14 0.46659(10) 0.1524(7) 0.3128(6) 0.0418(11) Uani d . 1 . .
H H14 0.4774 0.0387 0.2618 0.050 Uiso calc R 1 . .
O O15 0.44090(7) 0.1147(5) 0.3907(4) 0.0466(9) Uani d . 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
C2 C1 C6 . . 118.4(4) ?
C2 C1 C7 . . 121.3(4) ?
C6 C1 C7 . . 120.3(4) ?
C1 C2 C3 . . 121.5(4) ?
C1 C2 H2 . . 119.3 ?
C3 C2 H2 . . 119.3 ?
C4 C3 C2 . . 119.1(4) ?
C4 C3 H3 . . 120.4 ?
C2 C3 H3 . . 120.4 ?
C3 C4 O41 . . 125.1(4) ?
C3 C4 C5 . . 120.3(4) ?
O41 C4 C5 . . 114.6(4) ?
C4 O41 C42 . . 116.9(3) ?
O41 C42 H42A . . 109.5 ?
O41 C42 H42B . . 109.5 ?
H42A C42 H42B . . 109.5 ?
O41 C42 H42C . . 109.5 ?
H42A C42 H42C . . 109.5 ?
H42B C42 H42C . . 109.5 ?
C6 C5 C4 . . 119.4(4) ?
C6 C5 H5 . . 120.3 ?
C4 C5 H5 . . 120.3 ?
C1 C6 C5 . . 121.3(4) ?
C1 C6 H6 . . 119.3 ?
C5 C6 H6 . . 119.3 ?
C11 C7 C1 . . 114.3(3) ?
C11 C7 H7A . . 108.7 ?
C1 C7 H7A . . 108.7 ?
C11 C7 H7B . . 108.7 ?
C1 C7 H7B . . 108.7 ?
H7A C7 H7B . . 107.6 ?
C12 C11 O15 . . 110.0(3) ?
C12 C11 C7 . . 134.5(4) ?
O15 C11 C7 . . 115.5(4) ?
C11 C12 C13 . . 107.6(4) ?
C11 C12 H12 . . 126.2 ?
C13 C12 H12 . . 126.2 ?
C14 C13 C12 . . 105.7(3) ?
C14 C13 C31 . . 129.5(4) ?
C12 C13 C31 . . 124.8(4) ?
O32 C31 C13 . 2_655 118.3(2) ?
O32 C31 C13 . . 118.3(2) ?
C13 C31 C13 2_655 . 123.4(5) ?
C13 C14 O15 . . 110.5(3) ?
C13 C14 H14 . . 124.8 ?
O15 C14 H14 . . 124.8 ?
C14 O15 C11 . . 106.2(3) ?
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
C1 C2 . 1.380(6) ?
C1 C6 . 1.384(6) ?
C1 C7 . 1.518(5) ?
C2 C3 . 1.397(6) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.380(6) ?
C3 H3 . 0.9500 ?
C4 O41 . 1.383(5) ?
C4 C5 . 1.390(6) ?
O41 C42 . 1.426(5) ?
C42 H42A . 0.9800 ?
C42 H42B . 0.9800 ?
C42 H42C . 0.9800 ?
C5 C6 . 1.388(5) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C11 . 1.498(5) ?
C7 H7A . 0.9900 ?
C7 H7B . 0.9900 ?
C11 C12 . 1.321(6) ?
C11 O15 . 1.380(5) ?
C12 C13 . 1.433(5) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.344(6) ?
C13 C31 . 1.474(4) ?
C31 O32 . 1.231(7) ?
C31 C13 2_655 1.474(4) ?
C14 O15 . 1.368(5) ?
C14 H14 . 0.9500 ?
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
C14 H14 O32 1_545 0.95 2.23 3.114(5) 153.6
C12 H12 O15 1_565 0.95 2.87 3.782(5) 162.5
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
C6 C1 C2 C3 . . . . -0.2(6) ?
C7 C1 C2 C3 . . . . 179.5(4) ?
C1 C2 C3 C4 . . . . 0.4(6) ?
C2 C3 C4 O41 . . . . 179.1(4) ?
C2 C3 C4 C5 . . . . -0.3(6) ?
C3 C4 O41 C42 . . . . 1.0(6) ?
C5 C4 O41 C42 . . . . -179.6(4) ?
C3 C4 C5 C6 . . . . 0.0(6) ?
O41 C4 C5 C6 . . . . -179.4(3) ?
C2 C1 C6 C5 . . . . -0.1(6) ?
C7 C1 C6 C5 . . . . -179.8(4) ?
C4 C5 C6 C1 . . . . 0.2(6) ?
C2 C1 C7 C11 . . . . 113.0(4) ?
C6 C1 C7 C11 . . . . -67.3(5) ?
C1 C7 C11 C12 . . . . 108.1(5) ?
C1 C7 C11 O15 . . . . -70.6(5) ?
O15 C11 C12 C13 . . . . -1.9(4) ?
C7 C11 C12 C13 . . . . 179.3(4) ?
C11 C12 C13 C14 . . . . 1.3(5) ?
C11 C12 C13 C31 . . . . -179.5(3) ?
C14 C13 C31 O32 . . . . 170.0(4) ?
C12 C13 C31 O32 . . . . -9.0(4) ?
C14 C13 C31 C13 . . . 2_655 -10.0(4) ?
C12 C13 C31 C13 . . . 2_655 171.0(4) ?
C12 C13 C14 O15 . . . . -0.2(5) ?
C31 C13 C14 O15 . . . . -179.3(3) ?
C13 C14 O15 C11 . . . . -0.9(5) ?
C12 C11 O15 C14 . . . . 1.8(5) ?
C7 C11 O15 C14 . . . . -179.2(3) ?
