#------------------------------------------------------------------------------
#$Date: 2015-06-20 04:54:59 +0300 (Sat, 20 Jun 2015) $
#$Revision: 139439 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/08/2240845.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_2240845
loop_
_publ_author_name
'Knight, Kyle S.'
'Carey, Patrick J.'
_publ_section_title
;
 Crystal structure of
 (E)-4,4'-(but-2-ene-1,4-diyl)bis(2-methoxyphenol)
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o500
_journal_paper_doi               10.1107/S2056989015011585
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C18 H20 O4'
_chemical_formula_moiety         'C18 H20 O4'
_chemical_formula_sum            'C18 H20 O4'
_chemical_formula_weight         300.34
_chemical_name_systematic
;
(E)-4,4'-(But-2-ene-1,4-diyl)bis(2-methoxyphenol)
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.8846(2)
_cell_length_b                   10.7002(4)
_cell_length_c                   29.5666(11)
_cell_measurement_reflns_used    9944
_cell_measurement_temperature    198(2)
_cell_measurement_theta_max      24.75
_cell_measurement_theta_min      2.75
_cell_volume                     1545.33(10)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009) and Mercury (Macrae et
al.,  2008)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2014 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      198.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            25610
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.756
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.134
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         1352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0334
_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)+(0.0476P)²+0.3520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.0956
_reflns_number_gt                1199
_reflns_number_total             1352
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su5153sup1.cif
_cod_data_source_block           I
_cod_database_code               2240845
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.948
_shelx_estimated_absorpt_t_max   0.982
loop_
_space_group_symop_operation_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'
'-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_occupancy
O O1 0.3753(2) 0.94521(9) 0.20535(3) 0.0531(3) Uani d 1
C C1 0.1882(3) 1.04703(13) 0.20379(5) 0.0505(4) Uani d 1
H H1A 0.2599 1.1120 0.1837 0.076 Uiso calc 1
H H1B 0.1646 1.0815 0.2343 0.076 Uiso calc 1
H H1C 0.0111 1.0178 0.1924 0.076 Uiso calc 1
C C2 0.4437(3) 0.88991(11) 0.16499(4) 0.0395(3) Uani d 1
C C3 0.3285(3) 0.91684(12) 0.12337(4) 0.0454(3) Uani d 1
H H3 0.1922 0.9798 0.1211 0.054 Uiso calc 1
C C4 0.4108(3) 0.85237(13) 0.08473(4) 0.0475(4) Uani d 1
C C5 0.2924(3) 0.88644(16) 0.03888(4) 0.0605(4) Uani d 1
H H5A 0.3136 0.8146 0.0181 0.073 Uiso calc 1
H H5B 0.0941 0.9035 0.0422 0.073 Uiso calc 1
C C6 0.4294(3) 0.99880(15) 0.01871(4) 0.0554(4) Uani d 1
H H6 0.4116 1.0754 0.0347 0.066 Uiso calc 1
C C7 0.6459(3) 0.79875(11) 0.16851(4) 0.0419(3) Uani d 1
O O8 0.7636(2) 0.77137(10) 0.20946(3) 0.0556(3) Uani d 1
H H8 0.699(3) 0.8143(16) 0.2278(6) 0.067 Uiso d 1
C C9 0.6067(3) 0.76024(14) 0.08901(4) 0.0552(4) Uani d 1
H H9 0.6619 0.7143 0.0631 0.066 Uiso calc 1
C C10 0.7244(3) 0.73365(14) 0.13057(5) 0.0536(4) Uani d 1
H H10 0.8598 0.6702 0.1329 0.064 Uiso calc 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
C2 O1 C1 . 117.26(10)
O1 C1 H1A . 109.5
O1 C1 H1B . 109.5
O1 C1 H1C . 109.5
H1A C1 H1B . 109.5
H1A C1 H1C . 109.5
H1B C1 H1C . 109.5
O1 C2 C3 . 125.76(12)
O1 C2 C7 . 114.17(10)
C3 C2 C7 . 120.07(11)
C2 C3 H3 . 119.7
C2 C3 C4 . 120.59(13)
C4 C3 H3 . 119.7
C3 C4 C5 . 120.21(13)
C9 C4 C3 . 118.58(12)
C9 C4 C5 . 121.19(13)
C4 C5 H5A . 109.2
C4 C5 H5B . 109.2
H5A C5 H5B . 107.9
C6 C5 C4 . 112.18(12)
C6 C5 H5A . 109.2
C6 C5 H5B . 109.2
C5 C6 H6 . 116.9
C6 C6 C5 5_675 126.11(19)
C6 C6 H6 5_675 116.9
O8 C7 C2 . 120.87(11)
O8 C7 C10 . 119.65(12)
C10 C7 C2 . 119.46(11)
C7 O8 H8 . 108.7(13)
C4 C9 H9 . 119.5
C4 C9 C10 . 121.05(12)
C10 C9 H9 . 119.5
C7 C10 C9 . 120.23(13)
C7 C10 H10 . 119.9
C9 C10 H10 . 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C1 . 1.4228(16)
O1 C2 . 1.3732(15)
C1 H1A . 0.9800
C1 H1B . 0.9800
C1 H1C . 0.9800
C2 C3 . 1.3834(17)
C2 C7 . 1.3921(18)
C3 H3 . 0.9500
C3 C4 . 1.3938(18)
C4 C5 . 1.5183(17)
C4 C9 . 1.380(2)
C5 H5A . 0.9900
C5 H5B . 0.9900
C5 C6 . 1.500(2)
C6 C6 5_675 1.304(3)
C6 H6 . 0.9500
C7 O8 . 1.3720(15)
C7 C10 . 1.3751(19)
O8 H8 . 0.777(17)
C9 H9 . 0.9500
C9 C10 . 1.386(2)
C10 H10 . 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
O8 H8 O1 8_656 0.778(17) 2.571(17) 3.1784(13) 136.2(14)
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_4
_geom_torsion
O1 C2 C3 C4 . -178.58(12)
O1 C2 C7 O8 . -1.02(18)
O1 C2 C7 C10 . 177.67(12)
C1 O1 C2 C3 . -6.20(19)
C1 O1 C2 C7 . 174.44(11)
C2 C3 C4 C5 . -177.32(12)
C2 C3 C4 C9 . 0.8(2)
C2 C7 C10 C9 . 1.2(2)
C3 C2 C7 O8 . 179.57(12)
C3 C2 C7 C10 . -1.74(19)
C3 C4 C5 C6 . 80.50(17)
C3 C4 C9 C10 . -1.4(2)
C4 C5 C6 C6 5_675 116.9(2)
C4 C9 C10 C7 . 0.4(2)
C5 C4 C9 C10 . 176.73(13)
C7 C2 C3 C4 . 0.75(19)
O8 C7 C10 C9 . 179.89(13)
C9 C4 C5 C6 . -97.55(17)

_cod_database_fobs_code 2240845
