#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/70/2227014.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_2227014
loop_
_publ_author_name
'Kane, Christopher M.'
'Drake, Stephen D.'
'Holman, K. Travis'
_publ_section_title
;
 2-[4-(2,6-Dimethoxyphenyl)butyl]-1,3-dimethoxybenzene
;
_journal_coeditor_code           NG2784
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1921
_journal_paper_doi               10.1107/S1600536810025420
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H26 O4'
_chemical_formula_moiety         'C20 H26 O4'
_chemical_formula_sum            'C20 H26 O4'
_chemical_formula_weight         330.41
_chemical_melting_point_gt       429
_chemical_melting_point_lt       431
_chemical_name_systematic
;
2-[4-(2,6-Dimethoxyphenyl)butyl]-1,3-dimethoxybenzene
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.692(2)
_cell_length_b                   5.5460(5)
_cell_length_c                   13.7099(13)
_cell_measurement_reflns_used    6702
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.47
_cell_measurement_theta_min      2.97
_cell_volume                     1725.4(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material
'X-SEED (Barbour, 2001) and POV-RAY (Persistence of Vision, 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14196
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         1.79
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9811
_exptl_absorpt_correction_T_min  0.9155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.98
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.173
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2071
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0349
_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)+(0.0534P)²+0.4726P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                1853
_reflns_number_total             2071
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng2784.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 2yn'
_cod_database_code               2227014
_cod_database_fobs_code          2227014
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.15557(4) 0.35467(17) 0.12621(6) 0.0182(2) Uani d . 1 . .
C C2 0.19265(4) 0.29025(19) 0.20325(7) 0.0225(2) Uani d . 1 . .
C C3 0.18839(5) 0.4180(2) 0.28983(7) 0.0260(2) Uani d . 1 . .
C C4 0.14842(5) 0.6043(2) 0.30147(7) 0.0257(2) Uani d . 1 . .
C C5 0.11173(4) 0.66605(18) 0.22332(7) 0.0216(2) Uani d . 1 . .
C C6 0.11502(4) 0.54382(17) 0.13379(6) 0.0182(2) Uani d . 1 . .
C C7 0.07619(4) 0.61358(17) 0.04894(7) 0.0185(2) Uani d . 1 . .
C C8 0.01905(4) 0.46605(17) 0.04386(7) 0.0190(2) Uani d . 1 . .
C C9 0.06764(6) 0.9829(2) 0.31571(9) 0.0354(3) Uani d . 1 . .
C C10 0.19556(4) 0.04010(18) 0.02716(8) 0.0229(2) Uani d . 1 . .
H H2 0.2201(6) 0.161(2) 0.1972(9) 0.028(3) Uiso d . 1 . .
H H3 0.2143(5) 0.375(2) 0.3442(10) 0.030(3) Uiso d . 1 . .
H H4 0.1459(6) 0.689(3) 0.3613(10) 0.032(3) Uiso d . 1 . .
H H7A 0.0984(5) 0.588(2) -0.0112(9) 0.021(3) Uiso d . 1 . .
H H7B 0.0660(5) 0.785(2) 0.0535(8) 0.021(3) Uiso d . 1 . .
H H8A 0.0292(5) 0.292(2) 0.0404(8) 0.021(3) Uiso d . 1 . .
H H8B -0.0035(5) 0.491(2) 0.1046(8) 0.021(3) Uiso d . 1 . .
H H9A 0.1055(6) 1.065(2) 0.3276(10) 0.031(3) Uiso d . 1 . .
H H9B 0.0560(7) 0.878(3) 0.3713(12) 0.051(4) Uiso d . 1 . .
H H9C 0.0387(7) 1.102(3) 0.3050(11) 0.043(4) Uiso d . 1 . .
H H10A 0.2369(6) 0.091(2) 0.0350(8) 0.025(3) Uiso d . 1 . .
H H10B 0.1868(6) -0.085(2) 0.0749(10) 0.030(3) Uiso d . 1 . .
H H10C 0.1886(6) -0.025(3) -0.0395(10) 0.035(4) Uiso d . 1 . .
O O1 0.15679(3) 0.24072(13) 0.03720(5) 0.02170(18) Uani d . 1 . .
O O2 0.07098(3) 0.84683(14) 0.22717(5) 0.0297(2) 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
C1 O1 C10 . . 117.20(7) ?
C5 O2 C9 . . 117.13(9) ?
O2 C5 C4 . . 123.58(9) ?
O2 C5 C6 . . 115.11(8) ?
C4 C5 C6 . . 121.31(9) ?
C8 C8 C7 5_565 . 112.48(9) ?
C8 C8 H8A 5_565 . 109.4(7) ?
C7 C8 H8A . . 109.0(7) ?
C8 C8 H8B 5_565 . 109.6(7) ?
C7 C8 H8B . . 108.9(7) ?
H8A C8 H8B . . 107.3(10) ?
C1 C6 C5 . . 117.49(8) ?
C1 C6 C7 . . 121.24(8) ?
C5 C6 C7 . . 121.26(8) ?
O1 C1 C2 . . 122.79(9) ?
O1 C1 C6 . . 115.08(8) ?
C2 C1 C6 . . 122.12(9) ?
C6 C7 C8 . . 113.04(7) ?
C6 C7 H7B . . 109.7(7) ?
C8 C7 H7B . . 108.7(7) ?
C6 C7 H7A . . 108.2(7) ?
C8 C7 H7A . . 108.6(7) ?
H7B C7 H7A . . 108.5(10) ?
O1 C10 H10A . . 110.7(7) ?
O1 C10 H10C . . 105.8(8) ?
H10A C10 H10C . . 110.8(10) ?
O1 C10 H10B . . 111.4(8) ?
H10A C10 H10B . . 109.1(10) ?
H10C C10 H10B . . 109.0(11) ?
C3 C4 C5 . . 118.96(9) ?
C3 C4 H4 . . 120.7(8) ?
C5 C4 H4 . . 120.4(8) ?
C3 C2 C1 . . 118.36(9) ?
C3 C2 H2 . . 120.4(7) ?
C1 C2 H2 . . 121.3(7) ?
C4 C3 C2 . . 121.73(9) ?
C4 C3 H3 . . 119.2(8) ?
C2 C3 H3 . . 119.1(8) ?
O2 C9 H9A . . 109.7(8) ?
O2 C9 H9B . . 110.9(9) ?
H9A C9 H9B . . 111.9(12) ?
O2 C9 H9C . . 105.9(9) ?
H9A C9 H9C . . 108.2(12) ?
H9B C9 H9C . . 110.1(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
O1 C1 . 1.3746(11) ?
O1 C10 . 1.4251(11) ?
O2 C5 . 1.3650(13) ?
O2 C9 . 1.4314(12) ?
C5 C4 . 1.3992(14) ?
C5 C6 . 1.4042(13) ?
C8 C8 5_565 1.5283(18) ?
C8 C7 . 1.5349(12) ?
C8 H8A . 0.992(12) ?
C8 H8B . 0.987(11) ?
C6 C1 . 1.3993(13) ?
C6 C7 . 1.5096(12) ?
C1 C2 . 1.3967(13) ?
C7 H7B . 0.979(12) ?
C7 H7A . 0.976(12) ?
C10 H10A . 0.986(13) ?
C10 H10C . 0.995(14) ?
C10 H10B . 0.975(14) ?
C4 C3 . 1.3844(16) ?
C4 H4 . 0.947(14) ?
C2 C3 . 1.3857(14) ?
C2 H2 . 0.955(13) ?
C3 H3 . 0.979(13) ?
C9 H9A . 0.985(13) ?
C9 H9B . 0.994(16) ?
C9 H9C . 0.943(16) ?
