#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/39/2203917.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_2203917
loop_
_publ_author_name
'Guo-Wu Rao'
'Wei-Xiao Hu'
'Wei Zhou'
_publ_section_title
;
 10-(2-Methylbenzylidene)anthrone
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1234
_journal_page_last               o1235
_journal_paper_doi               10.1107/S1600536804014709
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C22 H16 O'
_chemical_formula_moiety         'C22 H16 O'
_chemical_formula_sum            'C22 H16 O'
_chemical_formula_weight         296.35
_chemical_melting_point          364.5(15)
_chemical_name_systematic
;
10-(2-methylbenzylidene)anthrone
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.020(5)
_cell_angle_beta                 91.224(4)
_cell_angle_gamma                100.854(8)
_cell_formula_units_Z            2
_cell_length_a                   7.0137(2)
_cell_length_b                   10.3135(4)
_cell_length_c                   11.5107(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      2.4
_cell_volume                     779.33(6)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2003)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω/2-θ
_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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5264
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.86
_diffrn_standards_decay_%        0.3
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.292
_refine_ls_extinction_coef       0.061(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0558
_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)+(0.1018P)²+0.0246P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1478
_refine_ls_wR_factor_ref         0.1710
_reflns_number_gt                2503
_reflns_number_total             3438
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6233.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '363-366' was changed to '364.5(15)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '363-366' was changed to '364.5(15)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2203917
_cod_database_fobs_code          2203917
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
O1 0.2292(2) 0.66826(14) 0.40091(11) 0.0691(4) Uani d . 1 O
C1 0.3235(2) 0.74692(16) 0.72480(14) 0.0445(4) Uani d . 1 C
C2 0.4094(3) 0.85931(18) 0.82410(16) 0.0582(5) Uani d . 1 C
H2 0.4242 0.8466 0.9003 0.070 Uiso calc R 1 H
C3 0.4724(3) 0.98833(19) 0.81128(17) 0.0683(6) Uani d . 1 C
H3 0.5315 1.0615 0.8783 0.082 Uiso calc R 1 H
C4 0.4488(3) 1.01036(19) 0.69975(18) 0.0643(5) Uani d . 1 C
H4 0.4871 1.0987 0.6921 0.077 Uiso calc R 1 H
C5 0.3687(3) 0.90134(18) 0.60069(16) 0.0550(4) Uani d . 1 C
H5 0.3524 0.9158 0.5254 0.066 Uiso calc R 1 H
C6 0.3114(2) 0.76899(16) 0.61114(14) 0.0449(4) Uani d . 1 C
C7 0.2543(2) 0.65021(18) 0.49927(14) 0.0480(4) Uani d . 1 C
C8 0.2446(2) 0.51083(16) 0.51144(14) 0.0447(4) Uani d . 1 C
C9 0.2269(2) 0.39863(19) 0.40572(15) 0.0547(4) Uani d . 1 C
H9 0.2195 0.4131 0.3298 0.066 Uiso calc R 1 H
C10 0.2203(3) 0.2681(2) 0.41258(18) 0.0629(5) Uani d . 1 C
H10 0.2064 0.1937 0.3418 0.075 Uiso calc R 1 H
C11 0.2344(3) 0.24716(19) 0.52520(18) 0.0628(5) Uani d . 1 C
H11 0.2321 0.1584 0.5300 0.075 Uiso calc R 1 H
C12 0.2517(3) 0.35615(18) 0.63039(17) 0.0554(4) Uani d . 1 C
H12 0.2622 0.3404 0.7056 0.067 Uiso calc R 1 H
C13 0.2537(2) 0.49013(16) 0.62569(14) 0.0438(4) Uani d . 1 C
C14 0.2540(2) 0.60763(16) 0.73635(14) 0.0445(4) Uani d . 1 C
C15 0.1792(3) 0.58418(17) 0.83613(14) 0.0510(4) Uani d . 1 C
H15 0.1610 0.4928 0.8369 0.061 Uiso calc R 1 H
C16 0.1215(2) 0.68109(16) 0.94493(14) 0.0474(4) Uani d . 1 C
C17 -0.0019(3) 0.76635(18) 0.93121(16) 0.0583(5) Uani d . 1 C
H17 -0.0349 0.7698 0.8536 0.070 Uiso calc R 1 H
C18 -0.0772(3) 0.84646(19) 1.03043(18) 0.0641(5) Uani d . 1 C
H18 -0.1613 0.9025 1.0197 0.077 Uiso calc R 1 H
C19 -0.0269(3) 0.84267(19) 1.14479(17) 0.0629(5) Uani d . 1 C
H19 -0.0768 0.8965 1.2122 0.075 Uiso calc R 1 H
C20 0.0969(3) 0.75957(18) 1.15996(15) 0.0549(5) Uani d . 1 C
H20 0.1303 0.7583 1.2382 0.066 Uiso calc R 1 H
C21 0.1732(2) 0.67764(16) 1.06202(15) 0.0475(4) Uani d . 1 C
C22 0.3104(3) 0.5899(2) 1.08140(18) 0.0672(5) Uani d . 1 C
H22A 0.3172 0.5922 1.1654 0.101 Uiso calc R 1 H
H22B 0.4375 0.6249 1.0605 0.101 Uiso calc R 1 H
H22C 0.2647 0.4962 1.0307 0.101 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
C2 C1 C6 117.66(15) ?
C2 C1 C14 122.10(14) ?
C6 C1 C14 120.20(14) ?
C3 C2 C1 121.09(16) ?
C3 C2 H2 119.5 ?
C1 C2 H2 119.5 ?
C2 C3 C4 120.56(17) ?
C2 C3 H3 119.7 ?
C4 C3 H3 119.7 ?
C5 C4 C3 119.39(17) ?
C5 C4 H4 120.3 ?
C3 C4 H4 120.3 ?
C4 C5 C6 120.74(17) ?
C4 C5 H5 119.6 ?
C6 C5 H5 119.6 ?
C5 C6 C1 120.36(15) ?
C5 C6 C7 119.15(14) ?
C1 C6 C7 120.26(14) ?
O1 C7 C8 121.85(15) yes
O1 C7 C6 120.93(16) yes
C8 C7 C6 117.05(13) ?
C13 C8 C9 120.13(16) ?
C13 C8 C7 121.21(14) ?
C9 C8 C7 118.66(15) ?
C10 C9 C8 120.69(17) ?
C10 C9 H9 119.7 ?
C8 C9 H9 119.7 ?
C9 C10 C11 119.59(17) ?
C9 C10 H10 120.2 ?
C11 C10 H10 120.2 ?
C12 C11 C10 120.64(18) ?
C12 C11 H11 119.7 ?
C10 C11 H11 119.7 ?
C11 C12 C13 120.80(17) ?
C11 C12 H12 119.6 ?
C13 C12 H12 119.6 ?
C8 C13 C12 118.10(15) ?
C8 C13 C14 119.42(14) ?
C12 C13 C14 122.39(14) ?
C15 C14 C1 123.81(15) yes
C15 C14 C13 119.85(15) yes
C1 C14 C13 116.13(13) ?
C14 C15 C16 129.89(15) yes
C14 C15 H15 115.1 ?
C16 C15 H15 115.1 ?
C17 C16 C21 119.27(16) ?
C17 C16 C15 119.64(15) yes
C21 C16 C15 120.74(15) yes
C18 C17 C16 121.24(16) ?
C18 C17 H17 119.4 ?
C16 C17 H17 119.4 ?
C19 C18 C17 119.41(18) ?
C19 C18 H18 120.3 ?
C17 C18 H18 120.3 ?
C18 C19 C20 120.02(17) ?
C18 C19 H19 120.0 ?
C20 C19 H19 120.0 ?
C19 C20 C21 121.71(16) ?
C19 C20 H20 119.1 ?
C21 C20 H20 119.1 ?
C20 C21 C16 118.34(16) ?
C20 C21 C22 120.56(15) ?
C16 C21 C22 121.08(16) ?
C21 C22 H22A 109.5 ?
C21 C22 H22B 109.5 ?
H22A C22 H22B 109.5 ?
C21 C22 H22C 109.5 ?
H22A C22 H22C 109.5 ?
H22B C22 H22C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 1.2143(18) yes
C1 C2 1.395(2) ?
C1 C6 1.396(2) ?
C1 C14 1.473(2) ?
C2 C3 1.373(2) ?
C2 H2 0.9300 ?
C3 C4 1.379(3) ?
C3 H3 0.9300 ?
C4 C5 1.365(3) ?
C4 H4 0.9300 ?
C5 C6 1.389(2) ?
C5 H5 0.9300 ?
C6 C7 1.480(2) ?
C7 C8 1.474(2) ?
C8 C13 1.395(2) ?
C8 C9 1.397(2) ?
C9 C10 1.363(3) ?
C9 H9 0.9300 ?
C10 C11 1.380(3) ?
C10 H10 0.9300 ?
C11 C12 1.375(2) ?
C11 H11 0.9300 ?
C12 C13 1.396(2) ?
C12 H12 0.9300 ?
C13 C14 1.479(2) ?
C14 C15 1.339(2) yes
C15 C16 1.474(2) ?
C15 H15 0.9300 ?
C16 C17 1.382(2) ?
C16 C21 1.400(2) ?
C17 C18 1.380(3) ?
C17 H17 0.9300 ?
C18 C19 1.369(3) ?
C18 H18 0.9300 ?
C19 C20 1.371(3) ?
C19 H19 0.9300 ?
C20 C21 1.382(2) ?
C20 H20 0.9300 ?
C21 C22 1.494(3) ?
C22 H22A 0.9600 ?
C22 H22B 0.9600 ?
C22 H22C 0.9600 ?
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
C6 C1 C2 C3 2.6(3) ?
C14 C1 C2 C3 -179.74(17) ?
C1 C2 C3 C4 1.2(3) ?
C2 C3 C4 C5 -2.5(3) ?
C3 C4 C5 C6 -0.1(3) ?
C4 C5 C6 C1 4.0(3) ?
C4 C5 C6 C7 -170.51(17) ?
C2 C1 C6 C5 -5.2(2) ?
C14 C1 C6 C5 177.12(15) ?
C2 C1 C6 C7 169.29(16) ?
C14 C1 C6 C7 -8.4(2) ?
C5 C6 C7 O1 -10.9(2) ?
C1 C6 C7 O1 174.54(16) ?
C5 C6 C7 C8 164.41(15) ?
C1 C6 C7 C8 -10.1(2) yes
O1 C7 C8 C13 -173.38(16) ?
C6 C7 C8 C13 11.4(2) yes
O1 C7 C8 C9 7.0(2) ?
C6 C7 C8 C9 -168.31(14) ?
C13 C8 C9 C10 -0.7(3) ?
C7 C8 C9 C10 179.01(16) ?
C8 C9 C10 C11 -1.0(3) ?
C9 C10 C11 C12 1.1(3) ?
C10 C11 C12 C13 0.6(3) ?
C9 C8 C13 C12 2.2(2) ?
C7 C8 C13 C12 -177.43(14) ?
C9 C8 C13 C14 -174.35(14) ?
C7 C8 C13 C14 6.0(2) ?
C11 C12 C13 C8 -2.2(3) ?
C11 C12 C13 C14 174.27(16) ?
C2 C1 C14 C15 33.2(3) ?
C6 C1 C14 C15 -149.24(17) ?
C2 C1 C14 C13 -152.20(16) ?
C6 C1 C14 C13 25.4(2) yes
C8 C13 C14 C15 150.80(17) ?
C12 C13 C14 C15 -25.6(2) ?
C8 C13 C14 C1 -24.1(2) yes
C12 C13 C14 C1 159.52(15) ?
C1 C14 C15 C16 10.2(3) ?
C13 C14 C15 C16 -164.27(17) ?
C14 C15 C16 C17 51.6(3) ?
C14 C15 C16 C21 -135.2(2) ?
C21 C16 C17 C18 -0.9(3) ?
C15 C16 C17 C18 172.34(17) ?
C16 C17 C18 C19 0.8(3) ?
C17 C18 C19 C20 -0.1(3) ?
C18 C19 C20 C21 -0.3(3) ?
C19 C20 C21 C16 0.1(3) ?
C19 C20 C21 C22 178.97(17) ?
C17 C16 C21 C20 0.5(2) ?
C15 C16 C21 C20 -172.71(15) ?
C17 C16 C21 C22 -178.35(17) ?
C15 C16 C21 C22 8.5(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21130676
