#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/64/2236414.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_2236414
loop_
_publ_author_name
'Ohta, Akira'
'Hattori, Kazuki'
'Kobayashi, Takashi'
'Naito, Hiroyoshi'
'Kawase, Takeshi'
'Kitamura, Chitoshi'
_publ_section_title
;
 2,6-Dimethoxy-9,10-anthraquinone
;
_journal_coeditor_code           KJ2210
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2843
_journal_paper_doi               10.1107/S1600536812037361
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C16 H12 O4'
_chemical_formula_moiety         'C16 H12 O4'
_chemical_formula_sum            'C16 H12 O4'
_chemical_formula_weight         268.26
_chemical_name_common
;
2,6-dimethoxy-9,10-anthraquinone
;
_chemical_name_systematic
;
2,6-dimethoxyanthracene-9,10-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 109.499(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.2689(19)
_cell_length_b                   3.9357(4)
_cell_length_c                   19.9510(19)
_cell_measurement_reflns_used    5015
_cell_measurement_temperature    223
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      3.185
_cell_volume                     1204.2(2)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1999)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      223
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.066
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10392
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.48
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.282
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2743
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.057
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0915P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.139
_refine_ls_wR_factor_ref         0.1783
_reflns_number_gt                1501
_reflns_number_total             2743
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kj2210.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               2236414
_cod_database_fobs_code          2236414
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_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 0.10535(16) 0.2528(6) 0.13534(12) 0.0412(6) Uani d . 1 1
H H1 0.0785 0.1497 0.1652 0.049 Uiso calc R 1 1
C C2 0.19519(17) 0.2826(6) 0.15742(12) 0.0424(6) Uani d . 1 1
C C3 0.23494(17) 0.4388(6) 0.11278(12) 0.0452(6) Uani d . 1 1
H H3 0.296 0.4582 0.1275 0.054 Uiso calc R 1 1
C C4 0.18464(17) 0.5631(6) 0.04772(12) 0.0444(6) Uani d . 1 1
H H4 0.2117 0.6696 0.0184 0.053 Uiso calc R 1 1
C C5 0.09401(16) 0.5337(6) 0.02449(11) 0.0387(6) Uani d . 1 1
C C6 0.05487(16) 0.3753(6) 0.06904(11) 0.0389(6) Uani d . 1 1
C C7 -0.04125(16) 0.3291(6) 0.04555(11) 0.0416(6) Uani d . 1 1
C C8 0.21230(19) 0.0119(7) 0.26849(13) 0.0522(7) Uani d . 1 1
H H8A 0.179 -0.1854 0.2455 0.078 Uiso calc R 1 1
H H8B 0.1741 0.1718 0.2805 0.078 Uiso calc R 1 1
H H8C 0.2581 -0.0583 0.3115 0.078 Uiso calc R 1 1
O O1 -0.07545(12) 0.1767(5) 0.08334(8) 0.0541(5) Uani d . 1 1
O O2 0.25054(12) 0.1718(5) 0.22088(8) 0.0506(5) Uani d . 1 1
C C9 0.47309(16) 0.1926(6) 0.36503(12) 0.0401(6) Uani d . 1 1
H H9 0.4168 0.1898 0.331 0.048 Uiso calc R 1 1
C C10 0.54271(17) 0.0488(6) 0.34963(12) 0.0424(6) Uani d . 1 1
C C11 0.62617(17) 0.0536(6) 0.39982(12) 0.0444(6) Uani d . 1 1
H H11 0.6731 -0.0422 0.3888 0.053 Uiso calc R 1 1
C C12 0.64007(17) 0.1983(6) 0.46545(12) 0.0430(6) Uani d . 1 1
H H12 0.6965 0.1982 0.4993 0.052 Uiso calc R 1 1
C C13 0.57121(15) 0.3458(6) 0.48250(11) 0.0380(6) Uani d . 1 1
C C14 0.48757(15) 0.3411(6) 0.43153(11) 0.0377(5) Uani d . 1 1
C C15 0.41234(15) 0.4966(6) 0.44723(12) 0.0409(6) Uani d . 1 1
C C16 0.45117(19) -0.1244(8) 0.23357(13) 0.0556(7) Uani d . 1 1
H H16A 0.4122 -0.2454 0.2529 0.083 Uiso calc R 1 1
H H16B 0.4552 -0.2453 0.1924 0.083 Uiso calc R 1 1
H H16C 0.4287 0.1026 0.2196 0.083 Uiso calc R 1 1
O O3 0.33925(12) 0.4938(5) 0.40245(8) 0.0542(5) Uani d . 1 1
O O4 0.53622(12) -0.1021(5) 0.28663(8) 0.0520(5) 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C2 C1 C6 . . 120.0(2)
C2 C1 H1 . . 120
C6 C1 H1 . . 120
O2 C2 C1 . . 124.8(2)
O2 C2 C3 . . 115.4(2)
C1 C2 C3 . . 119.7(2)
C4 C3 C2 . . 120.0(2)
C4 C3 H3 . . 120
C2 C3 H3 . . 120
C3 C4 C5 . . 121.0(2)
C3 C4 H4 . . 119.5
C5 C4 H4 . . 119.5
C4 C5 C6 . . 118.7(2)
C4 C5 C7 . 3_565 120.0(2)
C6 C5 C7 . 3_565 121.3(2)
C1 C6 C5 . . 120.6(2)
C1 C6 C7 . . 118.9(2)
C5 C6 C7 . . 120.5(2)
O1 C7 C5 . 3_565 121.2(2)
O1 C7 C6 . . 120.6(2)
C5 C7 C6 3_565 . 118.2(2)
O2 C8 H8A . . 109.5
O2 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
O2 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
C2 O2 C8 . . 117.2(2)
C10 C9 C14 . . 119.3(2)
C10 C9 H9 . . 120.3
C14 C9 H9 . . 120.3
O4 C10 C9 . . 124.3(2)
O4 C10 C11 . . 115.2(2)
C9 C10 C11 . . 120.4(2)
C12 C11 C10 . . 120.1(2)
C12 C11 H11 . . 120
C10 C11 H11 . . 120
C11 C12 C13 . . 120.8(2)
C11 C12 H12 . . 119.6
C13 C12 H12 . . 119.6
C12 C13 C14 . . 118.7(2)
C12 C13 C15 . 3_666 120.0(2)
C14 C13 C15 . 3_666 121.3(2)
C9 C14 C13 . . 120.7(2)
C9 C14 C15 . . 118.8(2)
C13 C14 C15 . . 120.6(2)
O3 C15 C13 . 3_666 121.4(2)
O3 C15 C14 . . 120.5(2)
C13 C15 C14 3_666 . 118.1(2)
O4 C16 H16A . . 109.5
O4 C16 H16B . . 109.5
H16A C16 H16B . . 109.5
O4 C16 H16C . . 109.5
H16A C16 H16C . . 109.5
H16B C16 H16C . . 109.5
C10 O4 C16 . . 117.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.384(4)
C1 C6 . 1.390(3)
C1 H1 . 0.94
C2 O2 . 1.357(3)
C2 C3 . 1.405(3)
C3 C4 . 1.373(3)
C3 H3 . 0.94
C4 C5 . 1.395(4)
C4 H4 . 0.94
C5 C6 . 1.401(3)
C5 C7 3_565 1.477(3)
C6 C7 . 1.486(3)
C7 O1 . 1.232(3)
C7 C5 3_565 1.477(3)
C8 O2 . 1.442(3)
C8 H8A . 0.97
C8 H8B . 0.97
C8 H8C . 0.97
C9 C10 . 1.389(3)
C9 C14 . 1.396(3)
C9 H9 . 0.94
C10 O4 . 1.362(3)
C10 C11 . 1.392(3)
C11 C12 . 1.376(3)
C11 H11 . 0.94
C12 C13 . 1.401(3)
C12 H12 . 0.94
C13 C14 . 1.401(3)
C13 C15 3_666 1.474(3)
C14 C15 . 1.492(3)
C15 O3 . 1.226(3)
C15 C13 3_666 1.474(3)
C16 O4 . 1.437(3)
C16 H16A . 0.97
C16 H16B . 0.97
C16 H16C . 0.97
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
C6 C1 C2 O2 . . -179.9(2)
C6 C1 C2 C3 . . 0.4(4)
O2 C2 C3 C4 . . -179.3(2)
C1 C2 C3 C4 . . 0.4(4)
C2 C3 C4 C5 . . -0.7(4)
C3 C4 C5 C6 . . 0.2(3)
C3 C4 C5 C7 . 3_565 179.7(2)
C2 C1 C6 C5 . . -0.9(4)
C2 C1 C6 C7 . . 177.9(2)
C4 C5 C6 C1 . . 0.6(3)
C7 C5 C6 C1 3_565 . -178.9(2)
C4 C5 C6 C7 . . -178.1(2)
C7 C5 C6 C7 3_565 . 2.4(4)
C1 C6 C7 O1 . . -1.9(3)
C5 C6 C7 O1 . . 176.8(2)
C1 C6 C7 C5 . 3_565 178.9(2)
C5 C6 C7 C5 . 3_565 -2.3(4)
C1 C2 O2 C8 . . -0.1(3)
C3 C2 O2 C8 . . 179.6(2)
C14 C9 C10 O4 . . -179.9(2)
C14 C9 C10 C11 . . -0.2(4)
O4 C10 C11 C12 . . -179.7(2)
C9 C10 C11 C12 . . 0.6(4)
C10 C11 C12 C13 . . -0.7(4)
C11 C12 C13 C14 . . 0.4(4)
C11 C12 C13 C15 . 3_666 -179.2(2)
C10 C9 C14 C13 . . -0.1(3)
C10 C9 C14 C15 . . 179.6(2)
C12 C13 C14 C9 . . 0.0(3)
C15 C13 C14 C9 3_666 . 179.6(2)
C12 C13 C14 C15 . . -179.7(2)
C15 C13 C14 C15 3_666 . -0.1(4)
C9 C14 C15 O3 . . -0.1(3)
C13 C14 C15 O3 . . 179.6(2)
C9 C14 C15 C13 . 3_666 -179.6(2)
C13 C14 C15 C13 . 3_666 0.1(4)
C9 C10 O4 C16 . . -2.3(3)
C11 C10 O4 C16 . . 178.0(2)
