#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/09/7150912.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7150912
loop_
_publ_author_name
'West, Kara'
'Wang, Changsheng'
'Batsanov, Andrei S.'
'Bryce, Martin R.'
_publ_section_title
;
 Carbon-rich molecules: synthesis and isolation of aryl/heteroaryl
 terminal bis(butadiynes)
 (HCC--CC--Ar--CC--CCH) and their
 applications in the synthesis of oligo(arylenebutadiynylene) molecular
 wires
;
_journal_issue                   11
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              1934
_journal_page_last               1937
_journal_paper_doi               10.1039/b802968g
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         'C19 H16 O3'
_chemical_formula_sum            'C19 H16 O3'
_chemical_formula_weight         292.32
_chemical_name_common
;6-(4-buta-1,3-diynyl-2,5-dimethoxyphenyl)-2-methylhexa-3,5-
diyn-2-ol
;
_chemical_name_systematic
; 6-(4-buta-1,3-diynyl-2,5-dimethoxyphenyl)-2-methylhexa-
3,5-diyn-2-ol
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.46(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.555(2)
_cell_length_b                   9.126(1)
_cell_length_c                   19.831(2)
_cell_measurement_reflns_used    2093
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.97
_cell_measurement_theta_min      2.53
_cell_volume                     3113.7(6)
_computing_cell_refinement       'SAINT version 6.45A (Bruker, 2003)'
_computing_data_collection       'SMART version 5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT version 6.45A (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL version 6.14 (Bruker, 2003)'
_computing_publication_material  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_refinement  'SHELXTL version 6.14 (Bruker, 2003)'
_computing_structure_solution    'SHELXTL version 6.14 (Bruker, 2003)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 6K CCD area detector'
_diffrn_measurement_method       '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  0.0676
_diffrn_reflns_av_sigmaI/netI    0.0800
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11371
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.10
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.903
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0444
_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)+(0.0406P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0945
_reflns_number_gt                1987
_reflns_number_total             3571
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b802968g.txt
_cod_data_source_block           5a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7150912
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.54645(7) 0.12119(13) 0.66339(6) 0.0286(3) Uani 1 1 d . . .
O2 O 0.56449(7) 0.72214(12) 0.69650(6) 0.0289(3) Uani 1 1 d . . .
O3 O 0.29417(8) 0.96900(15) 0.35288(6) 0.0370(4) Uani 1 1 d . . .
H0 H 0.3426(14) 0.960(3) 0.3433(13) 0.082(9) Uiso 1 1 d . . .
C1 C 0.54961(10) 0.27113(18) 0.66831(9) 0.0231(4) Uani 1 1 d . . .
C2 C 0.60210(10) 0.32724(19) 0.72527(8) 0.0229(4) Uani 1 1 d . . .
C3 C 0.60872(10) 0.47853(19) 0.73555(9) 0.0233(4) Uani 1 1 d . . .
H3 H 0.6435(9) 0.5166(19) 0.7734(8) 0.024(5) Uiso 1 1 d . . .
C4 C 0.56421(10) 0.57336(18) 0.69006(9) 0.0235(4) Uani 1 1 d . . .
C5 C 0.51356(9) 0.51782(19) 0.63158(8) 0.0218(4) Uani 1 1 d . . .
C6 C 0.50663(10) 0.36596(19) 0.62143(9) 0.0233(4) Uani 1 1 d . . .
H6 H 0.4719(9) 0.3333(17) 0.5810(8) 0.014(4) Uiso 1 1 d . . .
C7 C 0.64883(10) 0.22746(19) 0.77142(8) 0.0245(4) Uani 1 1 d . . .
C8 C 0.68722(10) 0.13751(19) 0.80756(9) 0.0251(4) Uani 1 1 d . . .
C9 C 0.72902(10) 0.0301(2) 0.84769(9) 0.0278(4) Uani 1 1 d . . .
C10 C 0.76438(13) -0.0650(2) 0.88060(10) 0.0385(5) Uani 1 1 d . . .
H10 H 0.7914(13) -0.140(2) 0.9060(11) 0.065(7) Uiso 1 1 d . . .
C11 C 0.46935(10) 0.61755(19) 0.58347(9) 0.0239(4) Uani 1 1 d . . .
C12 C 0.43212(10) 0.70450(19) 0.54496(9) 0.0240(4) Uani 1 1 d . . .
C13 C 0.38798(10) 0.80742(19) 0.50276(9) 0.0245(4) Uani 1 1 d . . .
C14 C 0.35040(10) 0.8979(2) 0.46763(9) 0.0247(4) Uani 1 1 d . . .
C15 C 0.30573(10) 1.0128(2) 0.42369(9) 0.0265(4) Uani 1 1 d . . .
C16 C 0.22474(12) 1.0270(3) 0.43865(12) 0.0397(5) Uani 1 1 d . . .
H161 H 0.1978(11) 0.930(2) 0.4277(9) 0.038(6) Uiso 1 1 d . . .
H162 H 0.2288(11) 1.061(2) 0.4869(10) 0.043(6) Uiso 1 1 d . . .
H163 H 0.1966(12) 1.103(2) 0.4076(11) 0.052(6) Uiso 1 1 d . . .
C17 C 0.34988(13) 1.1577(2) 0.43529(12) 0.0361(5) Uani 1 1 d . . .
H171 H 0.4001(12) 1.148(2) 0.4217(10) 0.046(6) Uiso 1 1 d . . .
H172 H 0.3544(11) 1.189(2) 0.4852(11) 0.045(6) Uiso 1 1 d . . .
H173 H 0.3228(11) 1.232(2) 0.4056(10) 0.045(6) Uiso 1 1 d . . .
C18 C 0.48364(12) 0.0582(2) 0.61467(11) 0.0295(4) Uani 1 1 d . . .
H181 H 0.4868(9) -0.053(2) 0.6243(8) 0.024(5) Uiso 1 1 d . . .
H182 H 0.4325(11) 0.099(2) 0.6222(9) 0.035(5) Uiso 1 1 d . . .
H183 H 0.4923(11) 0.077(2) 0.5659(10) 0.045(6) Uiso 1 1 d . . .
C19 C 0.61525(13) 0.7831(2) 0.75556(10) 0.0327(5) Uani 1 1 d . . .
H191 H 0.6707(11) 0.761(2) 0.7549(9) 0.032(5) Uiso 1 1 d . . .
H192 H 0.6009(11) 0.743(2) 0.7996(10) 0.047(6) Uiso 1 1 d . . .
H193 H 0.6048(10) 0.886(2) 0.7531(9) 0.036(5) Uiso 1 1 d . . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C18 117.54(14) . . ?
C4 O2 C19 116.90(14) . . ?
C15 O3 H0 105.9(16) . . ?
O1 C1 C6 124.65(16) . . ?
O1 C1 C2 115.56(14) . . ?
C6 C1 C2 119.78(16) . . ?
C3 C2 C1 119.98(15) . . ?
C3 C2 C7 121.06(16) . . ?
C1 C2 C7 118.95(16) . . ?
C4 C3 C2 120.40(16) . . ?
C4 C3 H3 119.2(11) . . ?
C2 C3 H3 120.4(11) . . ?
O2 C4 C3 125.02(16) . . ?
O2 C4 C5 115.18(14) . . ?
C3 C4 C5 119.80(16) . . ?
C6 C5 C4 119.77(15) . . ?
C6 C5 C11 120.87(16) . . ?
C4 C5 C11 119.36(15) . . ?
C1 C6 C5 120.20(16) . . ?
C1 C6 H6 122.9(9) . . ?
C5 C6 H6 116.9(9) . . ?
C8 C7 C2 176.39(18) . . ?
C7 C8 C9 177.62(19) . . ?
C10 C9 C8 178.1(2) . . ?
C9 C10 H10 179.2(15) . . ?
C12 C11 C5 177.73(19) . . ?
C11 C12 C13 177.6(2) . . ?
C14 C13 C12 178.62(19) . . ?
C13 C14 C15 178.30(19) . . ?
O3 C15 C14 109.44(14) . . ?
O3 C15 C16 105.05(15) . . ?
C14 C15 C16 110.62(16) . . ?
O3 C15 C17 110.95(16) . . ?
C14 C15 C17 109.31(15) . . ?
C16 C15 C17 111.40(18) . . ?
C15 C16 H161 107.6(11) . . ?
C15 C16 H162 108.9(11) . . ?
H161 C16 H162 114.8(16) . . ?
C15 C16 H163 108.0(12) . . ?
H161 C16 H163 108.9(15) . . ?
H162 C16 H163 108.4(16) . . ?
C15 C17 H171 109.7(12) . . ?
C15 C17 H172 109.2(11) . . ?
H171 C17 H172 113.2(16) . . ?
C15 C17 H173 110.0(12) . . ?
H171 C17 H173 105.2(16) . . ?
H172 C17 H173 109.5(16) . . ?
O1 C18 H181 105.3(9) . . ?
O1 C18 H182 109.8(10) . . ?
H181 C18 H182 110.6(14) . . ?
O1 C18 H183 109.2(11) . . ?
H181 C18 H183 109.4(14) . . ?
H182 C18 H183 112.4(15) . . ?
O2 C19 H191 111.1(10) . . ?
O2 C19 H192 109.8(11) . . ?
H191 C19 H192 110.2(15) . . ?
O2 C19 H193 105.0(11) . . ?
H191 C19 H193 112.0(15) . . ?
H192 C19 H193 108.6(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.372(2) . ?
O1 C18 1.434(2) . ?
O2 C4 1.364(2) . ?
O2 C19 1.435(2) . ?
O3 C15 1.435(2) . ?
O3 H0 0.91(2) . ?
C1 C6 1.380(2) . ?
C1 C2 1.405(2) . ?
C2 C3 1.397(2) . ?
C2 C7 1.429(2) . ?
C3 C4 1.376(2) . ?
C3 H3 0.935(16) . ?
C4 C5 1.408(2) . ?
C5 C6 1.402(2) . ?
C5 C11 1.431(2) . ?
C6 H6 0.954(16) . ?
C7 C8 1.204(2) . ?
C8 C9 1.378(3) . ?
C9 C10 1.185(3) . ?
C10 H10 0.92(2) . ?
C11 C12 1.201(2) . ?
C12 C13 1.387(3) . ?
C13 C14 1.191(2) . ?
C14 C15 1.484(2) . ?
C15 C16 1.515(3) . ?
C15 C17 1.527(3) . ?
C16 H161 1.003(19) . ?
C16 H162 0.994(19) . ?
C16 H163 0.99(2) . ?
C17 H171 0.98(2) . ?
C17 H172 1.02(2) . ?
C17 H173 0.96(2) . ?
C18 H181 1.031(18) . ?
C18 H182 1.011(19) . ?
C18 H183 1.02(2) . ?
C19 H191 0.997(18) . ?
C19 H192 1.02(2) . ?
C19 H193 0.96(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H0 O1 0.91(2) 2.11(3) 2.9946(19) 163(2) 5_666
C10 H10 C13 0.92(2) 2.76(2) 3.658(3) 165.6(19) 8_556
C10 H10 C14 0.92(2) 2.76(2) 3.668(3) 169.1(19) 8_556
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 O1 C18 -13.3(3) . . . . ?
C3 C4 O2 C19 -0.1(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653423
