#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/87/2238715.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_2238715
loop_
_publ_author_name
'Cheng, Hua'
_publ_section_title
;
 1,4-Bis(hexyloxy)benzene
;
_journal_coeditor_code           CV5434
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1721
_journal_paper_doi               10.1107/S1600536813029024
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C18 H30 O2'
_chemical_formula_moiety         'C18 H30 O2'
_chemical_formula_sum            'C18 H30 O2'
_chemical_formula_weight         278.42
_chemical_name_systematic
;
1,4-Bis(hexyloxy)benzene
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 95.674(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   18.853(12)
_cell_length_b                   7.512(5)
_cell_length_c                   6.364(4)
_cell_measurement_reflns_used    885
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.77
_cell_measurement_theta_min      2.17
_cell_volume                     896.9(10)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker 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  0.0991
_diffrn_reflns_av_sigmaI/netI    0.0758
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6024
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.9974
_exptl_absorpt_correction_T_min  0.9961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.031
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1552
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.1327
_refine_ls_R_factor_gt           0.0665
_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)+(0.1237P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1824
_refine_ls_wR_factor_ref         0.2384
_reflns_number_gt                760
_reflns_number_total             1552
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cv5434.cif
_cod_data_source_block           I
_cod_original_cell_volume        896.9(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2238715
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
C C1 0.01445(17) 0.4133(3) 0.8176(4) 0.0693(9) Uani d . 1 1
H H1 0.0241 0.3542 0.6952 0.083 Uiso calc R 1 1
C C2 0.06718(16) 0.5102(3) 0.9318(4) 0.0664(8) Uani d . 1 1
C C3 0.05200(17) 0.5954(4) 1.1147(4) 0.0700(8) Uani d . 1 1
H H3 0.0876 0.6597 1.1928 0.084 Uiso calc R 1 1
C C4 0.15191(16) 0.4640(4) 0.6777(4) 0.0795(9) Uani d . 1 1
H H4A 0.1171 0.5055 0.5661 0.095 Uiso calc R 1 1
H H4B 0.1514 0.3348 0.6782 0.095 Uiso calc R 1 1
C C5 0.22423(18) 0.5306(5) 0.6427(5) 0.0905(10) Uani d . 1 1
H H5A 0.2228 0.6595 0.6360 0.109 Uiso calc R 1 1
H H5B 0.2571 0.4978 0.7634 0.109 Uiso calc R 1 1
C C6 0.25233(18) 0.4623(5) 0.4483(5) 0.0959(11) Uani d . 1 1
H H6A 0.2207 0.4996 0.3269 0.115 Uiso calc R 1 1
H H6B 0.2520 0.3332 0.4520 0.115 Uiso calc R 1 1
C C7 0.3266(2) 0.5246(5) 0.4201(6) 0.1107(13) Uani d . 1 1
H H7A 0.3262 0.6535 0.4098 0.133 Uiso calc R 1 1
H H7B 0.3576 0.4929 0.5452 0.133 Uiso calc R 1 1
C C8 0.3570(3) 0.4521(8) 0.2347(7) 0.1542(19) Uani d . 1 1
H H8A 0.3263 0.4849 0.1095 0.185 Uiso calc R 1 1
H H8B 0.3569 0.3232 0.2443 0.185 Uiso calc R 1 1
C C9 0.4300(3) 0.5113(10) 0.2076(9) 0.202(3) Uani d . 1 1
H H9A 0.4313 0.6389 0.2018 0.303 Uiso calc R 1 1
H H9B 0.4444 0.4631 0.0787 0.303 Uiso calc R 1 1
H H9C 0.4619 0.4704 0.3245 0.303 Uiso calc R 1 1
O O1 0.13529(11) 0.5307(3) 0.8769(3) 0.0818(8) Uani d . 1 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
C3 C1 C2 3_567 119.7(3)
C3 C1 H1 3_567 120.2
C2 C1 H1 . 120.2
O1 C2 C1 . 124.7(3)
O1 C2 C3 . 116.0(2)
C1 C2 C3 . 119.3(3)
C1 C3 C2 3_567 121.1(2)
C1 C3 H3 3_567 119.5
C2 C3 H3 . 119.5
O1 C4 C5 . 107.4(3)
O1 C4 H4A . 110.2
C5 C4 H4A . 110.2
O1 C4 H4B . 110.2
C5 C4 H4B . 110.2
H4A C4 H4B . 108.5
C6 C5 C4 . 114.6(3)
C6 C5 H5A . 108.6
C4 C5 H5A . 108.6
C6 C5 H5B . 108.6
C4 C5 H5B . 108.6
H5A C5 H5B . 107.6
C5 C6 C7 . 113.9(3)
C5 C6 H6A . 108.8
C7 C6 H6A . 108.8
C5 C6 H6B . 108.8
C7 C6 H6B . 108.8
H6A C6 H6B . 107.7
C8 C7 C6 . 115.0(4)
C8 C7 H7A . 108.5
C6 C7 H7A . 108.5
C8 C7 H7B . 108.5
C6 C7 H7B . 108.5
H7A C7 H7B . 107.5
C7 C8 C9 . 115.2(5)
C7 C8 H8A . 108.5
C9 C8 H8A . 108.5
C7 C8 H8B . 108.5
C9 C8 H8B . 108.5
H8A C8 H8B . 107.5
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
C2 O1 C4 . 118.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C3 3_567 1.366(4)
C1 C2 . 1.380(4)
C1 H1 . 0.9300
C2 O1 . 1.372(3)
C2 C3 . 1.383(4)
C3 C1 3_567 1.366(4)
C3 H3 . 0.9300
C4 O1 . 1.427(3)
C4 C5 . 1.490(4)
C4 H4A . 0.9700
C4 H4B . 0.9700
C5 C6 . 1.484(4)
C5 H5A . 0.9700
C5 H5B . 0.9700
C6 C7 . 1.505(5)
C6 H6A . 0.9700
C6 H6B . 0.9700
C7 C8 . 1.467(5)
C7 H7A . 0.9700
C7 H7B . 0.9700
C8 C9 . 1.472(6)
C8 H8A . 0.9700
C8 H8B . 0.9700
C9 H9A . 0.9600
C9 H9B . 0.9600
C9 H9C . 0.9600
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_4
_geom_torsion
C3 C1 C2 O1 3_567 . -178.8(2)
C3 C1 C2 C3 3_567 . 0.7(4)
O1 C2 C3 C1 . 3_567 178.9(2)
C1 C2 C3 C1 . 3_567 -0.7(4)
O1 C4 C5 C6 . . 175.7(2)
C4 C5 C6 C7 . . -177.6(3)
C5 C6 C7 C8 . . 177.1(4)
C6 C7 C8 C9 . . -179.4(4)
C1 C2 O1 C4 . . 6.9(4)
C3 C2 O1 C4 . . -172.7(2)
C5 C4 O1 C2 . . 170.4(2)
