#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/07/7200779.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_7200779
loop_
_publ_author_name
'Harada, Jun'
'Harakawa, Mayuko'
'Sugiyama, Shingo'
'Ogawa, Keiichiro'
_publ_section_title
;
 Single crystal cis--trans photoisomerizations of
 2-(9-anthrylmethylene)-1-indanones
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              1235
_journal_paper_doi               10.1039/b821900a
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C24 H16 O'
_chemical_formula_weight         320.37
_chemical_melting_point          221
_chemical_name_systematic
;
(Z)-2-(9-anthrylmethylene)-1-indanone
;
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.865(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8957(11)
_cell_length_b                   13.8099(13)
_cell_length_c                   10.4687(10)
_cell_measurement_reflns_used    3715
_cell_measurement_temperature    300
_cell_measurement_theta_max      24.3
_cell_measurement_theta_min      2.3
_cell_volume                     1689.0(3)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD diffractometer'
_diffrn_measurement_method       ω_scan
_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  0.0479
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25437
_diffrn_reflns_theta_full        30.04
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9807
_exptl_absorpt_correction_T_min  0.9690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4942
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.1246
_refine_ls_R_factor_gt           0.0497
_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)+(0.0461P)²+0.3576P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1408
_reflns_number_gt                2326
_reflns_number_total             4942
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b821900a.txt
_cod_data_source_block           9a1i_90h
_cod_original_sg_symbol_H-M      P_1_21/a_1
_cod_database_code               7200779
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_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 1.09001(12) 0.26877(11) 0.83096(16) 0.0907(5) Uani 1 1 d . . .
C1 C 0.9664(2) -0.26539(16) 0.7166(2) 0.0769(6) Uani 1 1 d . . .
C2 C 1.0537(2) -0.25230(19) 0.6542(2) 0.0884(7) Uani 1 1 d . . .
C3 C 1.1002(2) -0.1594(2) 0.6461(2) 0.0880(7) Uani 1 1 d . . .
C4 C 1.05800(18) -0.08156(17) 0.7014(2) 0.0738(5) Uani 1 1 d . . .
C5 C 0.96564(15) -0.09173(12) 0.76943(16) 0.0559(4) Uani 1 1 d . . .
C6 C 0.91884(14) -0.01261(11) 0.82720(16) 0.0520(4) Uani 1 1 d . . .
C7 C 0.82610(14) -0.02695(11) 0.89074(16) 0.0516(4) Uani 1 1 d . . .
C8 C 0.77753(18) 0.04819(13) 0.95659(19) 0.0631(5) Uani 1 1 d . . .
C9 C 0.6886(2) 0.03099(16) 1.0171(2) 0.0766(6) Uani 1 1 d . . .
C10 C 0.6408(2) -0.06201(16) 1.0188(2) 0.0785(6) Uani 1 1 d . . .
C11 C 0.68544(18) -0.13587(15) 0.9613(2) 0.0716(6) Uani 1 1 d . . .
C12 C 0.77877(15) -0.12218(12) 0.89589(17) 0.0567(4) Uani 1 1 d . . .
C13 C 0.82659(17) -0.19876(13) 0.83918(19) 0.0638(5) Uani 1 1 d . . .
C14 C 0.91808(16) -0.18660(12) 0.77622(17) 0.0601(5) Uani 1 1 d . . .
C15 C 0.97258(16) 0.08372(12) 0.82346(18) 0.0574(4) Uani 1 1 d . . .
C16 C 0.92547(14) 0.16475(11) 0.77082(16) 0.0518(4) Uani 1 1 d . . .
C17 C 0.99301(16) 0.25574(12) 0.77183(18) 0.0586(4) Uani 1 1 d . . .
C18 C 0.92046(15) 0.32547(12) 0.68928(16) 0.0549(4) Uani 1 1 d . . .
C19 C 0.9464(2) 0.41949(14) 0.6545(2) 0.0701(5) Uani 1 1 d . . .
C20 C 0.8635(2) 0.47095(16) 0.5740(2) 0.0821(7) Uani 1 1 d . . .
C21 C 0.7572(2) 0.43084(16) 0.5293(2) 0.0847(7) Uani 1 1 d . . .
C22 C 0.7305(2) 0.33858(15) 0.5643(2) 0.0752(6) Uani 1 1 d . . .
C23 C 0.81406(15) 0.28501(12) 0.64420(17) 0.0555(4) Uani 1 1 d . . .
C24 C 0.80700(16) 0.18305(13) 0.6945(2) 0.0612(5) Uani 1 1 d . . .
H1 H 0.9318(16) -0.3290(15) 0.7253(19) 0.080(6) Uiso 1 1 d . . .
H2 H 1.0872(18) -0.3069(16) 0.617(2) 0.093(7) Uiso 1 1 d . . .
H3 H 1.167(2) -0.1485(16) 0.603(2) 0.100(7) Uiso 1 1 d . . .
H4 H 1.0932(17) -0.0176(15) 0.6973(19) 0.080(6) Uiso 1 1 d . . .
H8 H 0.8128(15) 0.1132(14) 0.9595(17) 0.068(5) Uiso 1 1 d . . .
H9 H 0.6547(18) 0.0847(16) 1.059(2) 0.097(7) Uiso 1 1 d . . .
H10 H 0.5753(18) -0.0716(14) 1.060(2) 0.085(6) Uiso 1 1 d . . .
H11 H 0.6552(16) -0.2004(15) 0.9622(19) 0.078(6) Uiso 1 1 d . . .
H13 H 0.7930(14) -0.2640(14) 0.8456(17) 0.067(5) Uiso 1 1 d . . .
H15 H 1.0545(16) 0.0852(13) 0.8615(18) 0.071(5) Uiso 1 1 d . . .
H19 H 1.0234(18) 0.4435(15) 0.690(2) 0.082(6) Uiso 1 1 d . . .
H20 H 0.8797(19) 0.5350(18) 0.545(2) 0.103(7) Uiso 1 1 d . . .
H21 H 0.699(2) 0.4695(18) 0.473(2) 0.114(8) Uiso 1 1 d . . .
H22 H 0.6572(17) 0.3113(14) 0.5410(19) 0.080(6) Uiso 1 1 d . . .
H241 H 0.7756(14) 0.1332(13) 0.6258(17) 0.061(5) Uiso 1 1 d . . .
H242 H 0.7473(17) 0.1776(13) 0.748(2) 0.083(6) 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
C2 C1 C14 121.5(2) . . ?
C1 C2 C3 120.2(2) . . ?
C4 C3 C2 120.9(2) . . ?
C3 C4 C5 121.1(2) . . ?
C6 C5 C4 122.76(17) . . ?
C6 C5 C14 119.62(16) . . ?
C4 C5 C14 117.61(17) . . ?
C7 C6 C5 120.10(15) . . ?
C7 C6 C15 121.38(15) . . ?
C5 C6 C15 118.48(15) . . ?
C6 C7 C8 123.48(15) . . ?
C6 C7 C12 119.68(15) . . ?
C8 C7 C12 116.79(16) . . ?
C9 C8 C7 121.48(18) . . ?
C8 C9 C10 121.3(2) . . ?
C11 C10 C9 119.5(2) . . ?
C10 C11 C12 121.67(19) . . ?
C13 C12 C11 121.67(17) . . ?
C13 C12 C7 119.17(17) . . ?
C11 C12 C7 119.14(16) . . ?
C14 C13 C12 122.27(17) . . ?
C13 C14 C1 122.19(19) . . ?
C13 C14 C5 119.16(16) . . ?
C1 C14 C5 118.65(19) . . ?
C16 C15 C6 128.30(17) . . ?
C15 C16 C17 121.62(16) . . ?
C15 C16 C24 130.05(15) . . ?
C17 C16 C24 108.17(14) . . ?
O1 C17 C18 126.97(16) . . ?
O1 C17 C16 125.95(17) . . ?
C18 C17 C16 107.08(15) . . ?
C23 C18 C19 121.25(18) . . ?
C23 C18 C17 109.63(14) . . ?
C19 C18 C17 129.12(18) . . ?
C20 C19 C18 118.3(2) . . ?
C19 C20 C21 120.5(2) . . ?
C20 C21 C22 121.6(2) . . ?
C21 C22 C23 118.6(2) . . ?
C18 C23 C22 119.75(17) . . ?
C18 C23 C24 111.42(15) . . ?
C22 C23 C24 128.83(18) . . ?
C16 C24 C23 103.51(14) . . ?
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 C17 1.216(2) . ?
C1 C2 1.340(3) . ?
C1 C14 1.428(3) . ?
C2 C3 1.406(4) . ?
C3 C4 1.360(3) . ?
C4 C5 1.425(3) . ?
C5 C6 1.413(2) . ?
C5 C14 1.434(2) . ?
C6 C7 1.406(2) . ?
C6 C15 1.480(2) . ?
C7 C8 1.427(2) . ?
C7 C12 1.436(2) . ?
C8 C9 1.353(3) . ?
C9 C10 1.406(3) . ?
C10 C11 1.344(3) . ?
C11 C12 1.422(3) . ?
C12 C13 1.386(2) . ?
C13 C14 1.385(3) . ?
C15 C16 1.324(2) . ?
C16 C17 1.490(2) . ?
C16 C24 1.505(2) . ?
C17 C18 1.462(3) . ?
C18 C23 1.383(2) . ?
C18 C19 1.399(2) . ?
C19 C20 1.369(3) . ?
C20 C21 1.379(3) . ?
C21 C22 1.379(3) . ?
C22 C23 1.386(3) . ?
C23 C24 1.511(2) . ?
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
C14 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -179.46(19) . . . . ?
C3 C4 C5 C14 -0.7(3) . . . . ?
C4 C5 C6 C7 178.65(16) . . . . ?
C14 C5 C6 C7 -0.1(2) . . . . ?
C4 C5 C6 C15 -3.7(2) . . . . ?
C14 C5 C6 C15 177.52(16) . . . . ?
C5 C6 C7 C8 176.97(16) . . . . ?
C15 C6 C7 C8 -0.6(3) . . . . ?
C5 C6 C7 C12 -0.4(2) . . . . ?
C15 C6 C7 C12 -177.94(15) . . . . ?
C6 C7 C8 C9 -179.65(18) . . . . ?
C12 C7 C8 C9 -2.2(3) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C8 C9 C10 C11 1.2(4) . . . . ?
C9 C10 C11 C12 -1.4(3) . . . . ?
C10 C11 C12 C13 178.5(2) . . . . ?
C10 C11 C12 C7 -0.3(3) . . . . ?
C6 C7 C12 C13 0.8(2) . . . . ?
C8 C7 C12 C13 -176.77(17) . . . . ?
C6 C7 C12 C11 179.56(16) . . . . ?
C8 C7 C12 C11 2.0(2) . . . . ?
C11 C12 C13 C14 -179.42(18) . . . . ?
C7 C12 C13 C14 -0.7(3) . . . . ?
C12 C13 C14 C1 -179.26(18) . . . . ?
C12 C13 C14 C5 0.2(3) . . . . ?
C2 C1 C14 C13 179.0(2) . . . . ?
C2 C1 C14 C5 -0.5(3) . . . . ?
C6 C5 C14 C13 0.2(2) . . . . ?
C4 C5 C14 C13 -178.60(17) . . . . ?
C6 C5 C14 C1 179.67(16) . . . . ?
C4 C5 C14 C1 0.9(3) . . . . ?
C7 C6 C15 C16 -62.0(3) . . . . ?
C5 C6 C15 C16 120.5(2) . . . . ?
C6 C15 C16 C17 -178.03(17) . . . . ?
C6 C15 C16 C24 -3.2(3) . . . . ?
C15 C16 C17 O1 -8.8(3) . . . . ?
C24 C16 C17 O1 175.4(2) . . . . ?
C15 C16 C17 C18 171.42(16) . . . . ?
C24 C16 C17 C18 -4.40(19) . . . . ?
O1 C17 C18 C23 -177.11(19) . . . . ?
C16 C17 C18 C23 2.65(19) . . . . ?
O1 C17 C18 C19 3.4(3) . . . . ?
C16 C17 C18 C19 -176.88(17) . . . . ?
C23 C18 C19 C20 -0.1(3) . . . . ?
C17 C18 C19 C20 179.39(19) . . . . ?
C18 C19 C20 C21 0.3(3) . . . . ?
C19 C20 C21 C22 0.4(4) . . . . ?
C20 C21 C22 C23 -1.3(3) . . . . ?
C19 C18 C23 C22 -0.8(3) . . . . ?
C17 C18 C23 C22 179.61(17) . . . . ?
C19 C18 C23 C24 179.73(17) . . . . ?
C17 C18 C23 C24 0.2(2) . . . . ?
C21 C22 C23 C18 1.5(3) . . . . ?
C21 C22 C23 C24 -179.2(2) . . . . ?
C15 C16 C24 C23 -171.03(18) . . . . ?
C17 C16 C24 C23 4.32(19) . . . . ?
C18 C23 C24 C16 -2.8(2) . . . . ?
C22 C23 C24 C16 177.79(19) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25940870
