#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:25:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180338 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/07/7200777.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_7200777
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                 101.625(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.7174(10)
_cell_length_b                   13.8685(12)
_cell_length_c                   10.5133(9)
_cell_measurement_reflns_used    6360
_cell_measurement_temperature    300
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.3
_cell_volume                     1673.4(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  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0357
_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            25403
_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    0.076
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_correction_T_min  0.9687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.272
_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         0.267
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4909
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0667
_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)+(0.0645P)²+0.8209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1560
_refine_ls_wR_factor_ref         0.1897
_reflns_number_gt                2762
_reflns_number_total             4909
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b821900a.txt
_cod_data_source_block           9a1i_50h
_cod_original_sg_symbol_H-M      P_1_21/a_1
_cod_database_code               7200777
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 0.7477(5) 0.1286(5) 0.6481(7) 0.0746(7) Uani 0.26 1 d P A 1
C1 C 0.9643(2) -0.26511(17) 0.7145(2) 0.0679(7) Uani 1 1 d . A 1
H1 H 0.9338 -0.3265 0.7204 0.081 Uiso 1 1 calc R A 1
C2 C 1.0513(3) -0.2532(2) 0.6508(3) 0.0785(8) Uani 1 1 d . A 1
H2 H 1.0803 -0.3058 0.6126 0.094 Uiso 1 1 calc R A 1
C3 C 1.0990(2) -0.1608(2) 0.6418(3) 0.0787(8) Uani 1 1 d . A 1
H3 H 1.1595 -0.1531 0.5974 0.094 Uiso 1 1 calc R A 1
C4 C 1.0582(2) -0.08296(19) 0.6969(2) 0.0646(6) Uani 1 1 d . A 1
H4 H 1.0910 -0.0227 0.6893 0.078 Uiso 1 1 calc R A 1
C5 C 0.96617(18) -0.09195(14) 0.7660(2) 0.0473(5) Uani 1 1 d . A 1
C6 C 0.92059(17) -0.01284(13) 0.82325(18) 0.0433(4) Uani 1 1 d . A 1
C7 C 0.82782(17) -0.02560(13) 0.88800(18) 0.0433(4) Uani 1 1 d . A 1
C8 C 0.7808(2) 0.05005(15) 0.9535(2) 0.0557(6) Uani 1 1 d . A 1
H8 H 0.8114 0.1119 0.9532 0.067 Uiso 1 1 calc R A 1
C9 C 0.6929(2) 0.03387(18) 1.0159(3) 0.0699(7) Uani 1 1 d . A 1
H9 H 0.6637 0.0849 1.0571 0.084 Uiso 1 1 calc R A 1
C10 C 0.6442(2) -0.05879(19) 1.0199(3) 0.0705(7) Uani 1 1 d . A 1
H10 H 0.5828 -0.0685 1.0625 0.085 Uiso 1 1 calc R A 1
C11 C 0.6871(2) -0.13297(17) 0.9620(2) 0.0629(6) Uani 1 1 d . A 1
H11 H 0.6554 -0.1941 0.9660 0.075 Uiso 1 1 calc R A 1
C12 C 0.77968(19) -0.12008(14) 0.8948(2) 0.0481(5) Uani 1 1 d . A 1
C13 C 0.8260(2) -0.19669(14) 0.8378(2) 0.0549(5) Uani 1 1 d . A 1
H13 H 0.7946 -0.2578 0.8428 0.066 Uiso 1 1 calc R A 1
C14 C 0.91724(19) -0.18581(14) 0.7736(2) 0.0513(5) Uani 1 1 d . A 1
C15 C 0.97790(18) 0.08196(14) 0.8206(2) 0.0492(5) Uani 1 1 d . A 1
H15 H 1.0564 0.0842 0.8598 0.059 Uiso 1 1 calc R A 1
C16A C 0.93226(17) 0.16413(13) 0.7699(2) 0.0448(4) Uani 0.26 1 d P A 1
C17A C 0.81344(19) 0.18378(15) 0.6914(2) 0.0534(5) Uani 0.26 1 d P A 1
C18A C 0.82041(19) 0.28570(14) 0.6457(2) 0.0482(5) Uani 0.26 1 d P A 1
C19 C 0.7354(2) 0.33962(17) 0.5662(2) 0.0646(6) Uani 1 1 d . A 1
H19 H 0.6615 0.3143 0.5354 0.078 Uiso 1 1 calc R A 1
C20 C 0.7632(3) 0.43208(18) 0.5336(3) 0.0725(7) Uani 1 1 d . A 1
H20 H 0.7073 0.4688 0.4791 0.087 Uiso 1 1 calc R A 1
C21 C 0.8717(3) 0.47100(16) 0.5803(2) 0.0706(7) Uani 1 1 d . A 1
H21 H 0.8879 0.5335 0.5572 0.085 Uiso 1 1 calc R A 1
C22 C 0.9559(2) 0.41853(15) 0.6606(2) 0.0606(6) Uani 1 1 d . A 1
H22 H 1.0291 0.4447 0.6925 0.073 Uiso 1 1 calc R A 1
C23A C 0.92888(19) 0.32493(14) 0.69305(19) 0.0475(5) Uani 0.26 1 d P A 1
C24A C 1.0036(2) 0.25419(15) 0.7750(2) 0.0535(5) Uani 0.26 1 d P A 1
H241 H 1.0256 0.2775 0.8636 0.064 Uiso 0.26 1 calc PR A 1
H242 H 1.0738 0.2422 0.7419 0.064 Uiso 0.26 1 calc PR A 1
O1B O 1.0997(2) 0.26512(17) 0.8330(3) 0.0746(7) Uani 0.74 1 d P B 2
C16B C 0.93226(17) 0.16413(13) 0.7699(2) 0.0448(4) Uani 0.74 1 d P B 2
C24B C 0.81344(19) 0.18378(15) 0.6914(2) 0.0534(5) Uani 0.74 1 d P B 2
H243 H 0.7949 0.1398 0.6185 0.064 Uiso 0.74 1 calc PR B 2
H244 H 0.7548 0.1776 0.7442 0.064 Uiso 0.74 1 calc PR B 2
C23B C 0.82041(19) 0.28570(14) 0.6457(2) 0.0482(5) Uani 0.74 1 d P B 2
C18B C 0.92888(19) 0.32493(14) 0.69305(19) 0.0475(5) Uani 0.74 1 d P B 2
C17B C 1.0036(2) 0.25419(15) 0.7750(2) 0.0535(5) Uani 0.74 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 121.5(2) . . ?
C1 C2 C3 120.0(2) . . ?
C4 C3 C2 121.1(3) . . ?
C3 C4 C5 121.1(2) . . ?
C6 C5 C4 122.85(19) . . ?
C6 C5 C14 119.63(19) . . ?
C4 C5 C14 117.50(19) . . ?
C7 C6 C5 120.42(17) . . ?
C7 C6 C15 121.29(17) . . ?
C5 C6 C15 118.17(18) . . ?
C6 C7 C8 123.63(18) . . ?
C6 C7 C12 119.32(17) . . ?
C8 C7 C12 116.99(19) . . ?
C9 C8 C7 121.4(2) . . ?
C8 C9 C10 121.4(2) . . ?
C11 C10 C9 119.6(2) . . ?
C10 C11 C12 121.5(2) . . ?
C13 C12 C11 121.64(19) . . ?
C13 C12 C7 119.18(19) . . ?
C11 C12 C7 119.17(19) . . ?
C14 C13 C12 122.48(19) . . ?
C13 C14 C1 122.2(2) . . ?
C13 C14 C5 118.97(18) . . ?
C1 C14 C5 118.8(2) . . ?
C16A C15 C6 128.62(19) . . ?
C15 C16A C17A 129.45(18) . . ?
C15 C16A C24A 121.72(19) . . ?
C17A C16A C24A 108.61(17) . . ?
O1A C17A C16A 126.2(4) . . ?
O1A C17A C18A 126.4(4) . . ?
C16A C17A C18A 104.12(17) . . ?
C23A C18A C19 120.2(2) . . ?
C23A C18A C17A 111.19(18) . . ?
C19 C18A C17A 128.6(2) . . ?
C20 C19 C18A 118.3(2) . . ?
C21 C20 C19 121.4(2) . . ?
C22 C21 C20 120.6(2) . . ?
C21 C22 C23A 118.3(2) . . ?
C18A C23A C22 121.1(2) . . ?
C18A C23A C24A 110.14(17) . . ?
C22 C23A C24A 128.8(2) . . ?
C23A C24A C16A 105.83(18) . . ?
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 1.115(6) . ?
C1 C2 1.338(4) . ?
C1 C14 1.427(3) . ?
C2 C3 1.408(4) . ?
C3 C4 1.357(3) . ?
C4 C5 1.422(3) . ?
C5 C6 1.407(3) . ?
C5 C14 1.431(3) . ?
C6 C7 1.405(3) . ?
C6 C15 1.479(3) . ?
C7 C8 1.426(3) . ?
C7 C12 1.434(3) . ?
C8 C9 1.346(3) . ?
C9 C10 1.410(3) . ?
C10 C11 1.344(3) . ?
C11 C12 1.421(3) . ?
C12 C13 1.384(3) . ?
C13 C14 1.383(3) . ?
C15 C16A 1.325(3) . ?
C16A C17A 1.493(3) . ?
C16A C24A 1.498(3) . ?
C17A C18A 1.501(3) . ?
C18A C23A 1.380(3) . ?
C18A C19 1.384(3) . ?
C19 C20 1.383(3) . ?
C20 C21 1.377(4) . ?
C21 C22 1.371(4) . ?
C22 C23A 1.395(3) . ?
C23A C24A 1.472(3) . ?
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 0.5(4) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
C3 C4 C5 C6 -179.3(2) . . . . ?
C3 C4 C5 C14 -0.9(3) . . . . ?
C4 C5 C6 C7 178.58(19) . . . . ?
C14 C5 C6 C7 0.2(3) . . . . ?
C4 C5 C6 C15 -5.4(3) . . . . ?
C14 C5 C6 C15 176.29(18) . . . . ?
C5 C6 C7 C8 176.91(19) . . . . ?
C15 C6 C7 C8 1.0(3) . . . . ?
C5 C6 C7 C12 -0.2(3) . . . . ?
C15 C6 C7 C12 -176.17(18) . . . . ?
C6 C7 C8 C9 -179.0(2) . . . . ?
C12 C7 C8 C9 -1.8(3) . . . . ?
C7 C8 C9 C10 0.5(4) . . . . ?
C8 C9 C10 C11 0.9(4) . . . . ?
C9 C10 C11 C12 -0.9(4) . . . . ?
C10 C11 C12 C13 178.4(2) . . . . ?
C10 C11 C12 C7 -0.4(3) . . . . ?
C6 C7 C12 C13 0.2(3) . . . . ?
C8 C7 C12 C13 -177.1(2) . . . . ?
C6 C7 C12 C11 179.05(19) . . . . ?
C8 C7 C12 C11 1.7(3) . . . . ?
C11 C12 C13 C14 -179.0(2) . . . . ?
C7 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C1 -179.7(2) . . . . ?
C12 C13 C14 C5 0.2(3) . . . . ?
C2 C1 C14 C13 178.9(2) . . . . ?
C2 C1 C14 C5 -1.1(4) . . . . ?
C6 C5 C14 C13 -0.2(3) . . . . ?
C4 C5 C14 C13 -178.7(2) . . . . ?
C6 C5 C14 C1 179.76(19) . . . . ?
C4 C5 C14 C1 1.3(3) . . . . ?
C7 C6 C15 C16A -62.4(3) . . . . ?
C5 C6 C15 C16A 121.6(2) . . . . ?
C6 C15 C16A C17A -5.6(4) . . . . ?
C6 C15 C16A C24A -179.6(2) . . . . ?
C15 C16A C17A O1A -11.3(6) . . . . ?
C24A C16A C17A O1A 163.3(5) . . . . ?
C15 C16A C17A C18A -171.6(2) . . . . ?
C24A C16A C17A C18A 3.0(2) . . . . ?
O1A C17A C18A C23A -161.8(5) . . . . ?
C16A C17A C18A C23A -1.5(2) . . . . ?
O1A C17A C18A C19 17.7(6) . . . . ?
C16A C17A C18A C19 178.0(2) . . . . ?
C23A C18A C19 C20 1.4(3) . . . . ?
C17A C18A C19 C20 -178.0(2) . . . . ?
C18A C19 C20 C21 -1.1(4) . . . . ?
C19 C20 C21 C22 0.3(4) . . . . ?
C20 C21 C22 C23A 0.2(4) . . . . ?
C19 C18A C23A C22 -1.0(3) . . . . ?
C17A C18A C23A C22 178.58(19) . . . . ?
C19 C18A C23A C24A 179.87(19) . . . . ?
C17A C18A C23A C24A -0.6(2) . . . . ?
C21 C22 C23A C18A 0.1(3) . . . . ?
C21 C22 C23A C24A 179.1(2) . . . . ?
C18A C23A C24A C16A 2.4(2) . . . . ?
C22 C23A C24A C16A -176.7(2) . . . . ?
C15 C16A C24A C23A 171.75(19) . . . . ?
C17A C16A C24A C23A -3.3(2) . . . . ?
