#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/71/2017172.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_2017172
loop_
_publ_author_name
'Sopková-de Oliveira Santos, Jana'
'Bazin, Marc-Antoine'
'Lohier, Jean-François'
'El Kihel, Laīla'
'Rault, Sylvain'
_publ_section_title
;
 1,2,3-Trimethoxy-4-[(E)-2-phenylvinyl]benzene and
 (E,E)-1,4-bis(2,3,4-trimethoxyphenyl)buta-1,3-diene
;
_journal_coeditor_code           FA3186
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o311
_journal_page_last               o313
_journal_paper_doi               10.1107/S0108270109019702
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C22 H26 O6'
_chemical_formula_moiety         'C22 H26 O6'
_chemical_formula_sum            'C22 H26 O6'
_chemical_formula_weight         386.43
_chemical_name_systematic
;
(E,E)-1,4-bis(2,3,4-trimethoxyphenyl)buta-1,3-diene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.138(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.2899(4)
_cell_length_b                   7.0186(3)
_cell_length_c                   13.9897(5)
_cell_measurement_reflns_used    9216
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      36.30
_cell_measurement_theta_min      2.25
_cell_volume                     987.76(7)
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2006)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30080
_diffrn_reflns_theta_full        34.97
_diffrn_reflns_theta_max         34.97
_diffrn_reflns_theta_min         2.25
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.275
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         4333
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0461
_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)+(0.0829P)²+0.1139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1357
_reflns_number_gt                3409
_reflns_number_total             4333
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fa3186.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2017172
_cod_database_fobs_code          2017172
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.28922(7) 0.06584(11) 0.12655(6) 0.01294(14) Uani d . 1 . .
C C2 0.29912(8) -0.06337(11) 0.20410(6) 0.01579(15) Uani d . 1 . .
H H2 0.2234(14) -0.150(2) 0.2091(10) 0.021(3) Uiso d . 1 . .
C C3 0.41067(8) -0.07076(11) 0.27982(6) 0.01584(15) Uani d . 1 . .
H H3 0.4118(14) -0.161(2) 0.3324(10) 0.026(3) Uiso d . 1 . .
C C4 0.51690(7) 0.05351(11) 0.28063(6) 0.01356(14) Uani d . 1 . .
C C5 0.51088(7) 0.18244(10) 0.20317(6) 0.01276(14) Uani d . 1 . .
C C6 0.39819(7) 0.18788(10) 0.12767(5) 0.01247(14) Uani d . 1 . .
C C7 0.17092(7) 0.08541(11) 0.04843(6) 0.01402(14) Uani d . 1 . .
H H7 0.1750(14) 0.1769(19) -0.0002(10) 0.021(3) Uiso d . 1 . .
C C8 0.05752(7) -0.01658(11) 0.03862(5) 0.01399(14) Uani d . 1 . .
H H8 0.0492(13) -0.117(2) 0.0854(9) 0.022(3) Uiso d . 1 . .
O O1 0.39277(6) 0.32140(8) 0.05491(4) 0.01553(13) Uani d . 1 . .
C C9 0.45411(10) 0.25947(14) -0.02267(7) 0.02239(18) Uani d . 1 . .
H H9A 0.5473(15) 0.221(2) 0.0032(11) 0.034(4) Uiso d . 1 . .
H H9B 0.4567(15) 0.365(2) -0.0674(11) 0.029(3) Uiso d . 1 . .
H H9C 0.4056(15) 0.149(2) -0.0570(10) 0.030(4) Uiso d . 1 . .
O O2 0.61634(6) 0.30017(8) 0.19888(4) 0.01464(12) Uani d . 1 . .
C C10 0.62063(9) 0.46692(12) 0.25903(6) 0.01910(16) Uani d . 1 . .
H H10A 0.6370(15) 0.4368(19) 0.3281(11) 0.026(3) Uiso d . 1 . .
H H10B 0.5335(15) 0.533(2) 0.2442(11) 0.033(4) Uiso d . 1 . .
H H10C 0.6886(13) 0.542(2) 0.2437(9) 0.021(3) Uiso d . 1 . .
O O3 0.62882(6) 0.06182(9) 0.35277(4) 0.01632(13) Uani d . 1 . .
C C11 0.64741(9) -0.08735(12) 0.42413(6) 0.01779(16) Uani d . 1 . .
H H11C 0.5806(15) -0.085(2) 0.4615(10) 0.025(3) Uiso d . 1 . .
H H11A 0.7306(15) -0.056(2) 0.4665(11) 0.031(4) Uiso d . 1 . .
H H11B 0.6526(14) -0.211(2) 0.3929(10) 0.026(3) Uiso 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 . . 117.19(7) ?
C2 C1 C7 . . 123.60(7) ?
C6 C1 C7 . . 119.15(7) ?
C3 C2 C1 . . 121.89(7) ?
C3 C2 H2 . . 117.0(8) ?
C1 C2 H2 . . 121.0(8) ?
C2 C3 C4 . . 120.16(7) ?
C2 C3 H3 . . 118.7(9) ?
C4 C3 H3 . . 121.1(9) ?
O3 C4 C3 . . 124.78(7) ?
O3 C4 C5 . . 115.93(7) ?
C3 C4 C5 . . 119.29(7) ?
O2 C5 C6 . . 119.23(7) ?
O2 C5 C4 . . 120.94(7) ?
C6 C5 C4 . . 119.80(7) ?
O1 C6 C5 . . 118.46(6) ?
O1 C6 C1 . . 119.84(7) ?
C5 C6 C1 . . 121.65(7) ?
C8 C7 C1 . . 126.30(7) ?
C8 C7 H7 . . 117.1(8) ?
C1 C7 H7 . . 116.6(8) ?
C7 C8 C8 . 3 123.04(9) ?
C7 C8 H8 . . 120.6(8) ?
C8 C8 H8 3 . 116.3(8) ?
C6 O1 C9 . . 113.45(6) ?
O1 C9 H9A . . 110.7(9) ?
O1 C9 H9B . . 109.4(9) ?
H9A C9 H9B . . 106.6(12) ?
O1 C9 H9C . . 110.3(9) ?
H9A C9 H9C . . 108.4(13) ?
H9B C9 H9C . . 111.4(12) ?
C5 O2 C10 . . 113.04(6) ?
O2 C10 H10A . . 112.6(8) ?
O2 C10 H10B . . 110.2(9) ?
H10A C10 H10B . . 105.7(12) ?
O2 C10 H10C . . 104.8(8) ?
H10A C10 H10C . . 111.7(12) ?
H10B C10 H10C . . 112.0(12) ?
C4 O3 C11 . . 116.94(6) ?
O3 C11 H11C . . 111.6(9) ?
O3 C11 H11A . . 103.7(9) ?
H11C C11 H11A . . 108.3(12) ?
O3 C11 H11B . . 110.5(8) ?
H11C C11 H11B . . 112.0(12) ?
H11A C11 H11B . . 110.5(12) ?
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 . 1.4012(11) ?
C1 C6 . 1.4085(10) ?
C1 C7 . 1.4614(10) y
C2 C3 . 1.3896(11) ?
C2 H2 . 1.001(14) ?
C3 C4 . 1.3966(11) ?
C3 H3 . 0.967(14) ?
C4 O3 . 1.3637(9) ?
C4 C5 . 1.4032(11) ?
C5 O2 . 1.3752(9) ?
C5 C6 . 1.3952(10) ?
C6 O1 . 1.3761(9) ?
C7 C8 . 1.3511(11) y
C7 H7 . 0.943(13) ?
C8 C8 3 1.4441(14) y
C8 H8 . 0.977(14) ?
O1 C9 . 1.4330(11) ?
C9 H9A . 0.988(15) ?
C9 H9B . 0.973(16) ?
C9 H9C . 0.992(16) ?
O2 C10 . 1.4367(10) ?
C10 H10A . 0.968(15) ?
C10 H10B . 0.992(16) ?
C10 H10C . 0.935(14) ?
O3 C11 . 1.4314(10) ?
C11 H11C . 0.947(15) ?
C11 H11A . 0.958(15) ?
C11 H11B . 0.979(14) ?
