#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/37/2013791.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_2013791
loop_
_publ_author_name
'Bruce, Michael I'
'Head, Nicholas J.'
'Skelton, Brian W.'
'White, Allan H.  '
_publ_section_title
;
 1,4-Diethynyl-2,5-dimethoxybenzene at ca 150 K
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o60
_journal_page_last               o61
_journal_paper_doi               10.1107/S0108270103027124
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C12 H10 O2'
_chemical_formula_moiety         'C12 H10 O2'
_chemical_formula_sum            'C12 H10 O2'
_chemical_formula_weight         186.21
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00000
_cell_angle_beta                 106.710(2)
_cell_angle_gamma                90.00000
_cell_formula_units_Z            2
_cell_length_a                   9.1110(10)
_cell_length_b                   5.9921(7)
_cell_length_c                   9.4080(10)
_cell_measurement_reflns_used    3004
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      34.6
_cell_measurement_theta_min      2.8
_cell_volume                     491.93(9)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'Xtal3.5 (Hall et al., 1995)'
_computing_molecular_graphics    Xtal3.5
_computing_publication_material  'BONDLA and CIFIO in Xtal3.5'
_computing_structure_refinement  'CRYLSQ in Xtal3.5'
_computing_structure_solution    Xtal3.5
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 1.0
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .025
_diffrn_reflns_av_sigmaI/netI    .06
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10271
_diffrn_reflns_theta_full        37.4
_diffrn_reflns_theta_max         37.4
_diffrn_reflns_theta_min         2.33
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    .085
_exptl_absorpt_correction_T_max  .93
_exptl_absorpt_correction_T_min  .77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             196
_exptl_crystal_size_max          .35
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .08
_refine_diff_density_max         .527
_refine_diff_density_min         -.206
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.032
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     84
_refine_ls_number_reflns         1957
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          .062
_refine_ls_R_factor_gt           .044
_refine_ls_shift/su_max          .005
_refine_ls_shift/su_mean         .001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(F) + 0.0003F²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         .054
_refine_ls_wR_factor_ref         .05
_reflns_number_gt                1957
_reflns_number_total             2574
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd1290.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-p 2ybc'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2013791
_cod_database_fobs_code          2013791
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
-x,1/2+y,1/2-z
-x,-y,-z
+x,1/2-y,1/2+z
loop_
_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_calc_attached_atom
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 .12902(9) .11388(15) .08619(9) .0184(3) Uani ? ? 1.00000 ? ?
C11 .26167(10) .22987(15) .17564(10) .0206(3) Uani ? ? 1.00000 ? ?
C12 .37230(11) .32442(18) .25064(11) .0253(4) Uani ? ? 1.00000 ? ?
C2 .14706(9) -.07129(15) .00091(9) .0185(3) Uani ? ? 1.00000 ? ?
O2 .29445(7) -.12925(12) .01094(7) .0232(3) Uani ? ? 1.00000 ? ?
C21 .31587(11) -.30991(18) -.08093(11) .0251(4) Uani ? ? 1.00000 ? ?
C3 .01834(9) -.18351(15) -.08506(9) .0199(3) Uani ? ? 1.00000 ? ?
H12 .4603(18) .398(3) .3090(17) .043(4) Uiso ? ? 1.00000 ? ?
H21a .4284(16) -.323(2) -.0608(15) .032(3) Uiso ? ? 1.00000 ? ?
H21b .2691(16) -.275(2) -.1866(15) .030(3) Uiso ? ? 1.00000 ? ?
H21c .2737(14) -.450(2) -.0564(14) .028(3) Uiso ? ? 1.00000 ? ?
H3 .0288(14) -.312(2) -.1451(14) .025(3) Uiso ? ? 1.00000 ? ?
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 .0136(3) .0204(4) .0185(3) .0000(3) .0003(2) -.0007(3)
C11 .0168(3) .0220(4) .0214(4) .0011(3) .0028(3) -.0002(3)
C12 .0189(4) .0276(4) .0266(4) -.0024(3) .0020(3) -.0029(3)
C2 .0125(3) .0219(4) .0190(3) .0020(3) .0011(2) .0000(3)
O2 .0132(2) .0290(3) .0250(3) .0036(2) .0019(2) -.0053(3)
C21 .0214(4) .0273(4) .0264(4) .0056(3) .0068(3) -.0025(3)
C3 .0151(3) .0217(4) .0205(3) .0011(3) .0012(2) -.0034(3)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C .002 .002 'Int Tables Vol IV Tables 2.2B and 2.3.1'
H 0 0 'Int Tables Vol IV Tables 2.2B and 2.3.1'
O .008 .006 'Int Tables Vol IV Tables 2.2B and 2.3.1'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
C11 C1 C2 . 119.93(8)
C11 C1 C3 3 120.15(8)
C2 C1 C3 3 119.92(7)
C1 C11 C12 . 179.39(11)
C11 C12 H12 . 179.1(11)
C1 C2 O2 . 115.83(7)
C1 C2 C3 . 119.71(8)
O2 C2 C3 . 124.45(8)
C2 O2 C21 . 116.92(7)
O2 C21 H21a . 104.9(8)
O2 C21 H21b . 110.7(8)
O2 C21 H21c . 112.1(9)
H21a C21 H21b . 109.4(12)
H21a C21 H21c . 110.0(11)
H21b C21 H21c . 109.6(11)
C2 C3 H3 . 120.8(7)
C2 C3 C1 3 120.36(8)
H3 C3 C1 3 118.9(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C11 . . 1.4377(11) ?
C1 C2 . . 1.4063(13) ?
C1 C3 . 3 1.4031(12) ?
C11 C12 . . 1.1941(12) ?
C12 H12 . . .940(14) ?
C2 O2 . . 1.3638(11) ?
C2 C3 . . 1.3914(11) ?
O2 C21 . . 1.4331(13) ?
C21 H21a . . .991(15) ?
C21 H21b . . .985(13) ?
C21 H21c . . .979(14) ?
C3 H3 . . .974(14) ?
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
_geom_hbond_publ_flag
C12 H12 O2 2_655 0.940(10) 2.390(10) 3.2270(10) 148.0(10) yes
