#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/12/2211205.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_2211205
loop_
_publ_author_name
'Neng-Fang She'
'Hui-Zhen Guo'
'Li-Ping Cao'
'Meng Gao'
_publ_section_title
;
 1,4-Bis(4-methoxyphenyl)buta-1,3-diyne
;
_journal_coeditor_code           SJ2137
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4958
_journal_page_last               o4959
_journal_paper_doi               10.1107/S1600536806041535
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H14 O2'
_chemical_formula_moiety         'C18 H14 O2'
_chemical_formula_sum            'C18 H14 O2'
_chemical_formula_weight         262.29
_chemical_name_systematic
;
1,4-bis(4-methoxyphenyl)buta-1,3-diyne
;
_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                 91.744(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2134(11)
_cell_length_b                   15.665(2)
_cell_length_c                   12.5861(18)
_cell_measurement_reflns_used    1211
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.74
_cell_measurement_theta_min      2.60
_cell_volume                     1421.5(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL  (Bruker, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 4K CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0700
_diffrn_reflns_av_sigmaI/netI    0.0719
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8416
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.08
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.232
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2788
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0584
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0795P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1758
_reflns_number_gt                1484
_reflns_number_total             2788
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj2137.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2211205
_cod_database_fobs_code          2211205
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
C C1 0.2765(4) 1.50218(17) 0.8559(2) 0.0742(10) Uani d . 1
H H1A 0.1462 1.4944 0.8661 0.111 Uiso calc R 1
H H1B 0.3059 1.5619 0.8595 0.111 Uiso calc R 1
H H1C 0.3459 1.4722 0.9105 0.111 Uiso calc R 1
C C2 0.2967(3) 1.38456(15) 0.7360(2) 0.0496(7) Uani d . 1
C C3 0.3571(4) 1.35495(16) 0.6393(2) 0.0540(7) Uani d . 1
H H3 0.4086 1.3926 0.5913 0.065 Uiso calc R 1
C C4 0.3409(4) 1.27017(16) 0.61449(19) 0.0530(7) Uani d . 1
H H4 0.3825 1.2507 0.5496 0.064 Uiso calc R 1
C C5 0.2633(3) 1.21273(15) 0.6845(2) 0.0484(7) Uani d . 1
C C6 0.1985(4) 1.24373(16) 0.7794(2) 0.0554(7) Uani d . 1
H H6 0.1424 1.2065 0.8262 0.066 Uiso calc R 1
C C7 0.2157(4) 1.32898(16) 0.8058(2) 0.0546(7) Uani d . 1
H H7 0.1730 1.3488 0.8703 0.066 Uiso calc R 1
C C8 0.2485(4) 1.12372(17) 0.6586(2) 0.0541(7) Uani d . 1
C C9 0.2396(4) 1.04948(17) 0.6376(2) 0.0546(7) Uani d . 1
C C10 0.2338(4) 0.96371(17) 0.6155(2) 0.0536(7) Uani d . 1
C C11 0.2314(4) 0.88875(17) 0.5959(2) 0.0529(7) Uani d . 1
C C12 0.2309(3) 0.79978(15) 0.5697(2) 0.0472(7) Uani d . 1
C C13 0.1532(4) 0.77088(16) 0.4751(2) 0.0583(8) Uani d . 1
H H13 0.0992 0.8100 0.4280 0.070 Uiso calc R 1
C C14 0.1533(4) 0.68574(17) 0.4484(2) 0.0593(8) Uani d . 1
H H14 0.0991 0.6678 0.3842 0.071 Uiso calc R 1
C C15 0.2337(4) 0.62737(16) 0.5168(2) 0.0526(7) Uani d . 1
C C16 0.3122(4) 0.65501(16) 0.6133(2) 0.0589(8) Uani d . 1
H H16 0.3666 0.6158 0.6601 0.071 Uiso calc R 1
C C17 0.3092(4) 0.73989(16) 0.6391(2) 0.0547(7) Uani d . 1
H H17 0.3603 0.7578 0.7041 0.066 Uiso calc R 1
C C18 0.1810(5) 0.51030(19) 0.3981(2) 0.0909(12) Uani d . 1
H H18A 0.0565 0.5300 0.3846 0.136 Uiso calc R 1
H H18B 0.1824 0.4490 0.3992 0.136 Uiso calc R 1
H H18C 0.2592 0.5305 0.3431 0.136 Uiso calc R 1
O O1 0.3233(3) 1.46949(11) 0.75415(15) 0.0649(6) Uani d . 1
O O2 0.2475(3) 0.54201(11) 0.49828(16) 0.0744(7) 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
_geom_angle_publ_flag
O1 C1 H1A 109.5 y
O1 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
O1 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
O1 C2 C7 124.8(2) y
O1 C2 C3 115.3(2) y
C7 C2 C3 119.9(2) y
C4 C3 C2 119.9(2) ?
C4 C3 H3 120.1 ?
C2 C3 H3 120.1 ?
C3 C4 C5 121.2(2) ?
C3 C4 H4 119.4 ?
C5 C4 H4 119.4 ?
C6 C5 C4 118.3(2) ?
C6 C5 C8 120.8(2) ?
C4 C5 C8 121.0(2) ?
C7 C6 C5 121.1(2) ?
C7 C6 H6 119.4 ?
C5 C6 H6 119.4 ?
C2 C7 C6 119.6(2) ?
C2 C7 H7 120.2 ?
C6 C7 H7 120.2 ?
C9 C8 C5 178.8(3) ?
C8 C9 C10 178.3(3) ?
C11 C10 C9 179.1(3) y
C10 C11 C12 178.4(3) y
C13 C12 C17 117.9(2) ?
C13 C12 C11 121.1(2) ?
C17 C12 C11 121.0(2) ?
C14 C13 C12 121.8(2) ?
C14 C13 H13 119.1 ?
C12 C13 H13 119.1 ?
C15 C14 C13 119.7(3) ?
C15 C14 H14 120.1 ?
C13 C14 H14 120.1 y
O2 C15 C14 125.3(2) ?
O2 C15 C16 115.1(2) ?
C14 C15 C16 119.5(2) ?
C17 C16 C15 120.0(2) ?
C17 C16 H16 120.0 ?
C15 C16 H16 120.0 ?
C16 C17 C12 121.0(2) ?
C16 C17 H17 119.5 ?
C12 C17 H17 119.5 ?
O2 C18 H18A 109.5 ?
O2 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
O2 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C2 O1 C1 117.6(2) y
C15 O2 C18 118.0(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 1.429(3) y
C1 H1A 0.9600 y
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 O1 1.363(3) y
C2 C7 1.379(3) y
C2 C3 1.386(3) ?
C3 C4 1.368(3) ?
C3 H3 0.9300 y
C4 C5 1.389(3) ?
C4 H4 0.9300 ?
C5 C6 1.384(3) ?
C5 C8 1.435(3) ?
C6 C7 1.381(3) ?
C6 H6 0.9300 ?
C7 H7 0.9300 ?
C8 C9 1.194(3) ?
C9 C10 1.373(4) ?
C10 C11 1.200(3) y
C11 C12 1.432(3) ?
C12 C13 1.377(3) ?
C12 C17 1.390(3) ?
C13 C14 1.376(3) ?
C13 H13 0.9300 ?
C14 C15 1.373(4) ?
C14 H14 0.9300 ?
C15 O2 1.362(3) ?
C15 C16 1.393(3) ?
C16 C17 1.369(3) ?
C16 H16 0.9300 ?
C17 H17 0.9300 ?
C18 O2 1.424(3) ?
C18 H18A 0.9600 ?
C18 H18B 0.9600 ?
C18 H18C 0.9600 ?
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
C16 H16 O1 1_545 0.93 2.60 3.404(2) 144.7
C3 H3 O2 1_565 0.93 2.85 3.504(2) 128.5
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
O1 C2 C3 C4 178.4(2)
C7 C2 C3 C4 -1.8(4)
C2 C3 C4 C5 0.5(4)
C3 C4 C5 C6 1.5(4)
C3 C4 C5 C8 -179.3(2)
C4 C5 C6 C7 -2.1(4)
C8 C5 C6 C7 178.7(2)
O1 C2 C7 C6 -179.0(2)
C3 C2 C7 C6 1.1(4)
C5 C6 C7 C2 0.8(4)
C17 C12 C13 C14 -0.6(4)
C11 C12 C13 C14 179.3(2)
C12 C13 C14 C15 -0.4(4)
C13 C14 C15 O2 -178.0(2)
C13 C14 C15 C16 0.8(4)
O2 C15 C16 C17 178.8(2)
C14 C15 C16 C17 -0.2(4)
C15 C16 C17 C12 -0.9(4)
C13 C12 C17 C16 1.2(4)
C11 C12 C17 C16 -178.6(2)
C7 C2 O1 C1 4.8(4)
C3 C2 O1 C1 -175.4(2)
C14 C15 O2 C18 2.9(4)
C16 C15 O2 C18 -176.0(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9185964
