#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:25:43 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180338 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/07/7200775.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_7200775
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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.408(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6272(8)
_cell_length_b                   13.9254(10)
_cell_length_c                   10.4577(8)
_cell_measurement_reflns_used    4100
_cell_measurement_temperature    300
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.8
_cell_volume                     1653.7(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0215
_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            25652
_diffrn_reflns_theta_full        30.02
_diffrn_reflns_theta_max         30.02
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.9684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.287
_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         0.259
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4837
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0530
_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)+(0.0695P)²+0.4591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1601
_reflns_number_gt                3385
_reflns_number_total             4837
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b821900a.txt
_cod_data_source_block           9a1i_30h
_cod_original_sg_symbol_H-M      P_1_21/a_1
_cod_database_code               7200775
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
O1A O 0.74635(13) 0.13632(11) 0.65511(17) 0.0574(4) Uani 0.74 1 d P A 1
C1 C 0.96104(18) -0.26287(12) 0.70981(18) 0.0607(5) Uani 1 1 d . A 1
H1 H 0.9293 -0.3235 0.7161 0.073 Uiso 1 1 calc R A 1
C2 C 1.04852(19) -0.25243(14) 0.6453(2) 0.0672(5) Uani 1 1 d . A 1
H2 H 1.0768 -0.3056 0.6077 0.081 Uiso 1 1 calc R A 1
C3 C 1.09729(18) -0.16117(16) 0.6344(2) 0.0677(5) Uani 1 1 d . A 1
H3 H 1.1574 -0.1544 0.5891 0.081 Uiso 1 1 calc R A 1
C4 C 1.05781(15) -0.08258(13) 0.68923(17) 0.0558(4) Uani 1 1 d . A 1
H4 H 1.0912 -0.0229 0.6804 0.067 Uiso 1 1 calc R A 1
C5 C 0.96615(13) -0.09000(10) 0.75988(14) 0.0430(3) Uani 1 1 d . A 1
C6 C 0.92321(13) -0.00986(10) 0.81801(14) 0.0401(3) Uani 1 1 d . A 1
C7 C 0.83090(13) -0.02144(10) 0.88489(14) 0.0401(3) Uani 1 1 d . A 1
C8 C 0.78657(15) 0.05497(11) 0.95170(16) 0.0510(4) Uani 1 1 d . A 1
H8 H 0.8180 0.1163 0.9502 0.061 Uiso 1 1 calc R A 1
C9 C 0.69979(18) 0.03988(13) 1.01705(19) 0.0625(5) Uani 1 1 d . A 1
H9 H 0.6728 0.0909 1.0599 0.075 Uiso 1 1 calc R A 1
C10 C 0.64926(18) -0.05190(14) 1.0215(2) 0.0651(5) Uani 1 1 d . A 1
H10 H 0.5889 -0.0607 1.0661 0.078 Uiso 1 1 calc R A 1
C11 C 0.68839(16) -0.12641(13) 0.96147(18) 0.0584(4) Uani 1 1 d . A 1
H11 H 0.6550 -0.1867 0.9654 0.070 Uiso 1 1 calc R A 1
C12 C 0.78035(14) -0.11469(10) 0.89164(15) 0.0453(3) Uani 1 1 d . A 1
C13 C 0.82417(15) -0.19253(10) 0.83389(16) 0.0507(4) Uani 1 1 d . A 1
H13 H 0.7912 -0.2529 0.8389 0.061 Uiso 1 1 calc R A 1
C14 C 0.91566(14) -0.18278(10) 0.76903(15) 0.0467(3) Uani 1 1 d . A 1
C15 C 0.98563(13) 0.08265(10) 0.81804(15) 0.0441(3) Uani 1 1 d . A 1
H15 H 1.0654 0.0814 0.8574 0.053 Uiso 1 1 calc R A 1
C16A C 0.94438(12) 0.16736(10) 0.77001(14) 0.0408(3) Uani 0.74 1 d P A 1
C17A C 0.82519(13) 0.18982(10) 0.68958(15) 0.0430(3) Uani 0.74 1 d P A 1
C18A C 0.83029(13) 0.29139(10) 0.64860(14) 0.0410(3) Uani 0.74 1 d P A 1
C19 C 0.74320(15) 0.34514(12) 0.56827(17) 0.0525(4) Uani 1 1 d . A 1
H19 H 0.6687 0.3196 0.5363 0.063 Uiso 1 1 calc R A 1
C20 C 0.77022(18) 0.43762(12) 0.53706(18) 0.0590(4) Uani 1 1 d . A 1
H20 H 0.7132 0.4749 0.4833 0.071 Uiso 1 1 calc R A 1
C21 C 0.88155(17) 0.47539(11) 0.58506(17) 0.0568(4) Uani 1 1 d . A 1
H21 H 0.8983 0.5375 0.5619 0.068 Uiso 1 1 calc R A 1
C22 C 0.96769(16) 0.42272(11) 0.66626(16) 0.0516(4) Uani 1 1 d . A 1
H22 H 1.0416 0.4490 0.6994 0.062 Uiso 1 1 calc R A 1
C23A C 0.94134(13) 0.32919(10) 0.69747(14) 0.0416(3) Uani 0.74 1 d P A 1
C24A C 1.01941(14) 0.25669(11) 0.77939(17) 0.0496(4) Uani 0.74 1 d P A 1
H241 H 1.0430 0.2783 0.8694 0.060 Uiso 0.74 1 calc PR A 1
H242 H 1.0894 0.2450 0.7453 0.060 Uiso 0.74 1 calc PR A 1
O1B O 1.1126(4) 0.2610(3) 0.8354(5) 0.0574(4) Uani 0.26 1 d P B 2
C16B C 0.94438(12) 0.16736(10) 0.77001(14) 0.0408(3) Uani 0.26 1 d P B 2
C24B C 0.82519(13) 0.18982(10) 0.68958(15) 0.0430(3) Uani 0.26 1 d P B 2
H243 H 0.8067 0.1480 0.6137 0.052 Uiso 0.26 1 calc PR B 2
H244 H 0.7656 0.1815 0.7408 0.052 Uiso 0.26 1 calc PR B 2
C23B C 0.83029(13) 0.29139(10) 0.64860(14) 0.0410(3) Uani 0.26 1 d P B 2
C18B C 0.94134(13) 0.32919(10) 0.69747(14) 0.0416(3) Uani 0.26 1 d P B 2
C17B C 1.01941(14) 0.25669(11) 0.77939(17) 0.0496(4) Uani 0.26 1 d P B 2
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 121.49(17) . . ?
C1 C2 C3 120.01(16) . . ?
C4 C3 C2 120.98(18) . . ?
C3 C4 C5 121.19(17) . . ?
C6 C5 C4 122.60(14) . . ?
C6 C5 C14 119.78(13) . . ?
C4 C5 C14 117.61(14) . . ?
C7 C6 C5 120.00(12) . . ?
C7 C6 C15 121.69(12) . . ?
C5 C6 C15 118.01(13) . . ?
C6 C7 C8 123.38(13) . . ?
C6 C7 C12 119.46(13) . . ?
C8 C7 C12 117.12(14) . . ?
C9 C8 C7 121.25(15) . . ?
C8 C9 C10 121.26(16) . . ?
C11 C10 C9 119.94(16) . . ?
C10 C11 C12 121.16(16) . . ?
C13 C12 C11 121.19(14) . . ?
C13 C12 C7 119.51(14) . . ?
C11 C12 C7 119.26(14) . . ?
C14 C13 C12 121.87(14) . . ?
C13 C14 C1 121.93(15) . . ?
C13 C14 C5 119.37(13) . . ?
C1 C14 C5 118.70(15) . . ?
C16A C15 C6 129.44(14) . . ?
C15 C16A C17A 127.92(13) . . ?
C15 C16A C24A 123.32(13) . . ?
C17A C16A C24A 108.52(12) . . ?
O1A C17A C18A 126.35(15) . . ?
O1A C17A C16A 127.48(14) . . ?
C18A C17A C16A 105.84(12) . . ?
C23A C18A C19 121.27(14) . . ?
C23A C18A C17A 110.34(13) . . ?
C19 C18A C17A 128.33(14) . . ?
C20 C19 C18A 118.20(16) . . ?
C19 C20 C21 120.65(16) . . ?
C22 C21 C20 121.31(15) . . ?
C21 C22 C23A 118.36(16) . . ?
C18A C23A C22 120.20(14) . . ?
C18A C23A C24A 110.91(12) . . ?
C22 C23A C24A 128.88(14) . . ?
C23A C24A C16A 104.33(12) . . ?
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
O1A C17A 1.176(2) . ?
C1 C2 1.344(3) . ?
C1 C14 1.430(2) . ?
C2 C3 1.406(3) . ?
C3 C4 1.360(2) . ?
C4 C5 1.425(2) . ?
C5 C6 1.412(2) . ?
C5 C14 1.431(2) . ?
C6 C7 1.411(2) . ?
C6 C15 1.4784(19) . ?
C7 C8 1.429(2) . ?
C7 C12 1.4334(19) . ?
C8 C9 1.351(2) . ?
C9 C10 1.412(3) . ?
C10 C11 1.342(3) . ?
C11 C12 1.428(2) . ?
C12 C13 1.390(2) . ?
C13 C14 1.386(2) . ?
C15 C16A 1.331(2) . ?
C16A C17A 1.492(2) . ?
C16A C24A 1.510(2) . ?
C17A C18A 1.4827(19) . ?
C18A C23A 1.386(2) . ?
C18A C19 1.388(2) . ?
C19 C20 1.381(2) . ?
C20 C21 1.387(3) . ?
C21 C22 1.377(3) . ?
C22 C23A 1.393(2) . ?
C23A C24A 1.498(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 -0.2(3) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 179.96(16) . . . . ?
C3 C4 C5 C14 -1.1(2) . . . . ?
C4 C5 C6 C7 178.93(14) . . . . ?
C14 C5 C6 C7 0.0(2) . . . . ?
C4 C5 C6 C15 -7.2(2) . . . . ?
C14 C5 C6 C15 173.88(13) . . . . ?
C5 C6 C7 C8 176.80(14) . . . . ?
C15 C6 C7 C8 3.2(2) . . . . ?
C5 C6 C7 C12 -0.8(2) . . . . ?
C15 C6 C7 C12 -174.45(13) . . . . ?
C6 C7 C8 C9 -178.43(16) . . . . ?
C12 C7 C8 C9 -0.7(2) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C11 C12 C13 177.37(18) . . . . ?
C10 C11 C12 C7 -0.5(3) . . . . ?
C6 C7 C12 C13 0.9(2) . . . . ?
C8 C7 C12 C13 -176.84(14) . . . . ?
C6 C7 C12 C11 178.87(14) . . . . ?
C8 C7 C12 C11 1.1(2) . . . . ?
C11 C12 C13 C14 -178.12(16) . . . . ?
C7 C12 C13 C14 -0.2(2) . . . . ?
C12 C13 C14 C1 179.85(15) . . . . ?
C12 C13 C14 C5 -0.6(2) . . . . ?
C2 C1 C14 C13 178.89(17) . . . . ?
C2 C1 C14 C5 -0.7(3) . . . . ?
C6 C5 C14 C13 0.7(2) . . . . ?
C4 C5 C14 C13 -178.28(15) . . . . ?
C6 C5 C14 C1 -179.74(14) . . . . ?
C4 C5 C14 C1 1.3(2) . . . . ?
C7 C6 C15 C16A -63.2(2) . . . . ?
C5 C6 C15 C16A 123.05(18) . . . . ?
C6 C15 C16A C17A -7.2(3) . . . . ?
C6 C15 C16A C24A 179.04(15) . . . . ?
C15 C16A C17A O1A 0.5(3) . . . . ?
C24A C16A C17A O1A 175.00(18) . . . . ?
C15 C16A C17A C18A -173.18(15) . . . . ?
C24A C16A C17A C18A 1.36(16) . . . . ?
O1A C17A C18A C23A -173.47(17) . . . . ?
C16A C17A C18A C23A 0.27(16) . . . . ?
O1A C17A C18A C19 3.6(3) . . . . ?
C16A C17A C18A C19 177.31(15) . . . . ?
C23A C18A C19 C20 0.5(2) . . . . ?
C17A C18A C19 C20 -176.25(15) . . . . ?
C18A C19 C20 C21 0.0(3) . . . . ?
C19 C20 C21 C22 -0.9(3) . . . . ?
C20 C21 C22 C23A 1.3(2) . . . . ?
C19 C18A C23A C22 -0.1(2) . . . . ?
C17A C18A C23A C22 177.20(13) . . . . ?
C19 C18A C23A C24A -179.11(14) . . . . ?
C17A C18A C23A C24A -1.83(17) . . . . ?
C21 C22 C23A C18A -0.8(2) . . . . ?
C21 C22 C23A C24A 178.03(15) . . . . ?
C18A C23A C24A C16A 2.57(17) . . . . ?
C22 C23A C24A C16A -176.34(15) . . . . ?
C15 C16A C24A C23A 172.50(14) . . . . ?
C17A C16A C24A C23A -2.34(16) . . . . ?
