#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/70/2207037.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_2207037
loop_
_publ_author_name
'Wei Zhou'
'Weixiao Hu'
'Chunnian Xia'
_publ_section_title
;
 10-(3,4-Dimethoxybenzylidene)anthrone
;
_journal_coeditor_code           OB6581
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3433
_journal_page_last               o3434
_journal_paper_doi               10.1107/S1600536805028278
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C23 H18 O3'
_chemical_formula_moiety         'C23 H18 O3'
_chemical_formula_sum            'C23 H18 O3'
_chemical_formula_weight         342.37
_chemical_melting_point          .453E-305
_chemical_name_systematic
;
10-(3,4-Dimethoxybenzylidene)anthrone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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
_cell_angle_beta                 103.36(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.709(3)
_cell_length_b                   10.306(2)
_cell_length_c                   14.847(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      13.99
_cell_measurement_theta_min      10.65
_cell_volume                     1743.1(9)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD (McArdle, 2000)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            3529
_diffrn_reflns_theta_full        25.17
_diffrn_reflns_theta_max         25.17
_diffrn_reflns_theta_min         2.00
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.128
_refine_ls_extinction_coef       0.0133(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0353
_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)+(0.0484P)²+0.3183P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.1096
_reflns_number_gt                1832
_reflns_number_total             3136
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6581.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2207037
_cod_database_fobs_code          2207037
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 -0.07769(13) 0.91670(16) 0.26699(11) 0.0853(5) Uani d . 1 O
O2 0.48952(12) 0.24924(13) 0.60172(9) 0.0618(4) Uani d . 1 O
O3 0.45078(12) 0.13957(13) 0.44370(9) 0.0628(4) Uani d . 1 O
C1 0.07187(19) 1.0518(2) 0.41341(15) 0.0614(6) Uani d . 1 C
H1 0.0141 1.1001 0.3740 0.074 Uiso calc R 1 H
C2 0.1505(2) 1.1133(2) 0.48267(16) 0.0665(6) Uani d . 1 C
H2 0.1465 1.2026 0.4902 0.080 Uiso calc R 1 H
C3 0.2351(2) 1.0416(2) 0.54095(16) 0.0669(6) Uani d . 1 C
H3 0.2884 1.0828 0.5886 0.080 Uiso calc R 1 H
C4 0.24224(17) 0.90959(18) 0.52979(15) 0.0587(5) Uani d . 1 C
H4 0.3006 0.8631 0.5701 0.070 Uiso calc R 1 H
C5 0.17147(15) 0.70174(17) 0.44396(12) 0.0448(4) Uani d . 1 C
C6 0.03917(17) 0.5061(2) 0.40338(14) 0.0565(5) Uani d . 1 C
H6 0.0957 0.4547 0.4414 0.068 Uiso calc R 1 H
C7 -0.0657(2) 0.4513(2) 0.35799(16) 0.0725(7) Uani d . 1 C
H7 -0.0794 0.3636 0.3659 0.087 Uiso calc R 1 H
C8 -0.1508(2) 0.5259(3) 0.30062(17) 0.0828(8) Uani d . 1 C
H8 -0.2210 0.4883 0.2694 0.099 Uiso calc R 1 H
C9 -0.13106(18) 0.6547(3) 0.29017(16) 0.0739(7) Uani d . 1 C
H9 -0.1883 0.7047 0.2516 0.089 Uiso calc R 1 H
C10 -0.01277(16) 0.8539(2) 0.32866(14) 0.0576(5) Uani d . 1 C
C11 0.16388(14) 0.84343(17) 0.45934(12) 0.0454(5) Uani d . 1 C
C12 0.06211(15) 0.63806(18) 0.39324(12) 0.0451(4) Uani d . 1 C
C13 -0.02637(15) 0.7128(2) 0.33644(13) 0.0523(5) Uani d . 1 C
C14 0.07668(16) 0.91733(18) 0.40075(13) 0.0481(5) Uani d . 1 C
C15 0.27495(15) 0.64083(18) 0.47521(14) 0.0533(5) Uani d . 1 C
H15 0.3329 0.6926 0.5114 0.064 Uiso calc R 1 H
C16 0.31284(15) 0.50738(18) 0.46252(13) 0.0489(5) Uani d . 1 C
C17 0.38052(15) 0.44288(18) 0.53917(13) 0.0476(5) Uani d . 1 C
H17 0.3966 0.4832 0.5968 0.057 Uiso calc R 1 H
C18 0.42387(15) 0.32021(17) 0.53070(13) 0.0467(5) Uani d . 1 C
C19 0.40288(16) 0.25983(18) 0.44413(13) 0.0494(5) Uani d . 1 C
C20 0.33782(16) 0.3241(2) 0.36780(14) 0.0546(5) Uani d . 1 C
H20 0.3239 0.2850 0.3098 0.066 Uiso calc R 1 H
C21 0.29319(17) 0.4466(2) 0.37722(14) 0.0570(5) Uani d . 1 C
H21 0.2492 0.4887 0.3253 0.068 Uiso calc R 1 H
C22 0.5087(2) 0.3023(2) 0.69236(13) 0.0698(6) Uani d . 1 C
H22A 0.5503 0.3829 0.6946 0.105 Uiso calc R 1 H
H22B 0.5542 0.2426 0.7359 0.105 Uiso calc R 1 H
H22C 0.4346 0.3172 0.7078 0.105 Uiso calc R 1 H
C23 0.4107(2) 0.0596(2) 0.36466(14) 0.0699(6) Uani d . 1 C
H23A 0.3265 0.0549 0.3507 0.105 Uiso calc R 1 H
H23B 0.4429 -0.0260 0.3771 0.105 Uiso calc R 1 H
H23C 0.4356 0.0958 0.3128 0.105 Uiso calc R 1 H
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
C18 O2 C22 117.57(15) ?
C19 O3 C23 118.29(15) ?
C2 C1 C14 121.2(2) ?
C2 C1 H1 119.4 ?
C14 C1 H1 119.4 ?
C1 C2 C3 119.2(2) ?
C1 C2 H2 120.4 ?
C3 C2 H2 120.4 ?
C2 C3 C4 120.8(2) ?
C2 C3 H3 119.6 ?
C4 C3 H3 119.6 ?
C3 C4 C11 121.65(19) ?
C3 C4 H4 119.2 ?
C11 C4 H4 119.2 ?
C15 C5 C12 124.86(17) yes
C15 C5 C11 119.09(16) yes
C12 C5 C11 116.04(15) ?
C7 C6 C12 121.1(2) ?
C7 C6 H6 119.4 ?
C12 C6 H6 119.4 ?
C6 C7 C8 120.4(2) ?
C6 C7 H7 119.8 ?
C8 C7 H7 119.8 ?
C9 C8 C7 119.6(2) ?
C9 C8 H8 120.2 ?
C7 C8 H8 120.2 ?
C8 C9 C13 121.0(2) ?
C8 C9 H9 119.5 ?
C13 C9 H9 119.5 ?
O1 C10 C14 121.6(2) ?
O1 C10 C13 121.3(2) ?
C14 C10 C13 117.08(16) ?
C4 C11 C14 117.16(17) ?
C4 C11 C5 122.85(16) ?
C14 C11 C5 119.97(16) ?
C6 C12 C13 117.61(18) ?
C6 C12 C5 122.71(17) ?
C13 C12 C5 119.57(17) ?
C9 C13 C12 120.2(2) ?
C9 C13 C10 118.97(19) ?
C12 C13 C10 120.73(17) ?
C1 C14 C11 119.97(19) ?
C1 C14 C10 119.62(18) ?
C11 C14 C10 120.35(17) ?
C5 C15 C16 131.69(18) yes
C5 C15 H15 114.2 ?
C16 C15 H15 114.2 ?
C21 C16 C17 118.28(17) ?
C21 C16 C15 123.32(17) yes
C17 C16 C15 118.17(18) yes
C18 C17 C16 120.92(18) ?
C18 C17 H17 119.5 ?
C16 C17 H17 119.5 ?
O2 C18 C17 125.05(17) ?
O2 C18 C19 114.82(16) ?
C17 C18 C19 120.12(17) ?
O3 C19 C20 125.66(18) ?
O3 C19 C18 115.12(16) ?
C20 C19 C18 119.21(18) ?
C19 C20 C21 120.25(19) ?
C19 C20 H20 119.9 ?
C21 C20 H20 119.9 ?
C16 C21 C20 121.20(18) ?
C16 C21 H21 119.4 ?
C20 C21 H21 119.4 ?
O2 C22 H22A 109.5 ?
O2 C22 H22B 109.5 ?
H22A C22 H22B 109.5 ?
O2 C22 H22C 109.5 ?
H22A C22 H22C 109.5 ?
H22B C22 H22C 109.5 ?
O3 C23 H23A 109.5 ?
O3 C23 H23B 109.5 ?
H23A C23 H23B 109.5 ?
O3 C23 H23C 109.5 ?
H23A C23 H23C 109.5 ?
H23B C23 H23C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C10 1.230(2) yes
O2 C18 1.365(2) ?
O2 C22 1.421(2) ?
O3 C19 1.361(2) ?
O3 C23 1.422(2) ?
C1 C2 1.367(3) ?
C1 C14 1.401(3) ?
C1 H1 0.9300 ?
C2 C3 1.371(3) ?
C2 H2 0.9300 ?
C3 C4 1.376(3) ?
C3 H3 0.9300 ?
C4 C11 1.399(3) ?
C4 H4 0.9300 ?
C5 C15 1.348(2) yes
C5 C12 1.480(2) yes
C5 C11 1.484(3) yes
C6 C7 1.378(3) ?
C6 C12 1.401(3) ?
C6 H6 0.9300 ?
C7 C8 1.385(3) ?
C7 H7 0.9300 ?
C8 C9 1.362(3) ?
C8 H8 0.9300 ?
C9 C13 1.394(3) ?
C9 H9 0.9300 ?
C10 C14 1.467(3) yes
C10 C13 1.471(3) yes
C11 C14 1.403(2) yes
C12 C13 1.405(2) yes
C15 C16 1.471(3) ?
C15 H15 0.9300 ?
C16 C21 1.384(3) ?
C16 C17 1.396(2) ?
C17 C18 1.379(2) ?
C17 H17 0.9300 ?
C18 C19 1.398(3) ?
C19 C20 1.380(3) ?
C20 C21 1.386(3) ?
C20 H20 0.9300 ?
C21 H21 0.9300 ?
C22 H22A 0.9599 ?
C22 H22B 0.9599 ?
C22 H22C 0.9599 ?
C23 H23A 0.9599 ?
C23 H23B 0.9599 ?
C23 H23C 0.9599 ?
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_publ_flag
C14 C1 C2 C3 -0.3(3) ?
C1 C2 C3 C4 0.6(3) ?
C2 C3 C4 C11 -0.2(3) ?
C12 C6 C7 C8 0.4(3) ?
C6 C7 C8 C9 -0.9(4) ?
C7 C8 C9 C13 0.0(4) ?
C3 C4 C11 C14 -0.6(3) ?
C3 C4 C11 C5 178.21(19) ?
C15 C5 C11 C4 -22.9(3) ?
C12 C5 C11 C4 157.81(17) ?
C15 C5 C11 C14 155.82(18) ?
C12 C5 C11 C14 -23.5(2) ?
C7 C6 C12 C13 1.0(3) ?
C7 C6 C12 C5 177.26(18) ?
C15 C5 C12 C6 26.4(3) ?
C11 C5 C12 C6 -154.39(17) ?
C15 C5 C12 C13 -157.46(19) ?
C11 C5 C12 C13 21.8(2) yes
C8 C9 C13 C12 1.5(3) ?
C8 C9 C13 C10 -175.3(2) ?
C6 C12 C13 C9 -2.0(3) ?
C5 C12 C13 C9 -178.32(17) ?
C6 C12 C13 C10 174.80(17) ?
C5 C12 C13 C10 -1.5(3) yes
O1 C10 C13 C9 -17.1(3) ?
C14 C10 C13 C9 159.28(18) ?
O1 C10 C13 C12 166.05(18) ?
C14 C10 C13 C12 -17.5(3) yes
C2 C1 C14 C11 -0.5(3) ?
C2 C1 C14 C10 176.92(18) ?
C4 C11 C14 C1 0.9(3) ?
C5 C11 C14 C1 -177.93(17) ?
C4 C11 C14 C10 -176.50(17) ?
C5 C11 C14 C10 4.7(3) yes
O1 C10 C14 C1 14.9(3) ?
C13 C10 C14 C1 -161.51(17) ?
O1 C10 C14 C11 -167.72(18) ?
C13 C10 C14 C11 15.9(3) ?
C12 C5 C15 C16 6.5(3) yes
C11 C5 C15 C16 -172.7(2) no
C5 C15 C16 C21 48.2(3) yes
C5 C15 C16 C17 -137.3(2) no
C21 C16 C17 C18 -1.9(3) ?
C15 C16 C17 C18 -176.59(16) ?
C22 O2 C18 C17 4.1(3) ?
C22 O2 C18 C19 -176.72(18) ?
C16 C17 C18 O2 -179.21(17) ?
C16 C17 C18 C19 1.6(3) ?
C23 O3 C19 C20 -15.3(3) ?
C23 O3 C19 C18 164.97(18) ?
O2 C18 C19 O3 0.1(2) ?
C17 C18 C19 O3 179.34(16) ?
O2 C18 C19 C20 -179.68(17) ?
C17 C18 C19 C20 -0.4(3) ?
O3 C19 C20 C21 179.76(18) ?
C18 C19 C20 C21 -0.5(3) ?
C17 C16 C21 C20 0.9(3) ?
C15 C16 C21 C20 175.36(18) ?
C19 C20 C21 C16 0.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3663563
