#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/07/7200773.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_7200773
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                 102.513(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6222(8)
_cell_length_b                   13.9067(9)
_cell_length_c                   10.3985(7)
_cell_measurement_reflns_used    4703
_cell_measurement_temperature    300
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.3
_cell_volume                     1640.75(19)
_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  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0249
_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            25420
_diffrn_reflns_theta_full        30.02
_diffrn_reflns_theta_max         30.02
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9801
_exptl_absorpt_correction_T_min  0.9681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.297
_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         0.283
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4801
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0461
_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)+(0.0722P)²+0.3205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1213
_refine_ls_wR_factor_ref         0.1390
_reflns_number_gt                3591
_reflns_number_total             4801
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b821900a.txt
_cod_data_source_block           9a1i_0h
_cod_original_sg_symbol_H-M      P_1_21/a_1
_cod_database_code               7200773
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 0.74615(8) 0.13915(6) 0.65900(10) 0.0487(2) Uani 1 1 d . . .
C1 C 0.95978(15) -0.26171(10) 0.70763(15) 0.0541(3) Uani 1 1 d . . .
C2 C 1.04771(16) -0.25159(12) 0.64234(16) 0.0600(4) Uani 1 1 d . . .
C3 C 1.09721(15) -0.16019(13) 0.63114(16) 0.0590(4) Uani 1 1 d . . .
C4 C 1.05805(13) -0.08103(11) 0.68618(14) 0.0495(3) Uani 1 1 d . . .
C5 C 0.96640(10) -0.08806(8) 0.75764(11) 0.0380(3) Uani 1 1 d . . .
C6 C 0.92438(10) -0.00762(8) 0.81643(11) 0.0352(2) Uani 1 1 d . . .
C7 C 0.83221(10) -0.01864(8) 0.88396(11) 0.0359(2) Uani 1 1 d . . .
C8 C 0.78904(13) 0.05802(9) 0.95175(13) 0.0449(3) Uani 1 1 d . . .
C9 C 0.70251(14) 0.04311(11) 1.01872(15) 0.0546(4) Uani 1 1 d . . .
C10 C 0.65101(15) -0.04869(12) 1.02304(16) 0.0584(4) Uani 1 1 d . . .
C11 C 0.68882(14) -0.12344(11) 0.96103(15) 0.0530(3) Uani 1 1 d . . .
C12 C 0.78066(11) -0.11205(8) 0.89049(12) 0.0403(3) Uani 1 1 d . . .
C13 C 0.82337(13) -0.19016(9) 0.83189(14) 0.0455(3) Uani 1 1 d . . .
C14 C 0.91524(12) -0.18090(8) 0.76671(12) 0.0418(3) Uani 1 1 d . . .
C15 C 0.98862(11) 0.08426(8) 0.81719(12) 0.0381(3) Uani 1 1 d . . .
C16 C 0.94920(10) 0.17033(8) 0.77053(11) 0.0345(2) Uani 1 1 d . . .
C17 C 0.82965(9) 0.19374(8) 0.69004(11) 0.0336(2) Uani 1 1 d . . .
C18 C 0.83380(10) 0.29512(8) 0.64953(11) 0.0345(2) Uani 1 1 d . . .
C19 C 0.74549(12) 0.34858(9) 0.56862(13) 0.0447(3) Uani 1 1 d . . .
C20 C 0.77194(14) 0.44121(10) 0.53655(15) 0.0499(3) Uani 1 1 d . . .
C21 C 0.88363(14) 0.47915(9) 0.58502(14) 0.0484(3) Uani 1 1 d . . .
C22 C 0.97113(13) 0.42666(9) 0.66678(13) 0.0438(3) Uani 1 1 d . . .
C23 C 0.94535(10) 0.33286(8) 0.69887(11) 0.0351(2) Uani 1 1 d . . .
C24 C 1.02490(11) 0.26000(9) 0.78081(14) 0.0428(3) Uani 1 1 d . . .
H1 H 0.9232(16) -0.3258(13) 0.7163(17) 0.065(5) Uiso 1 1 d . . .
H2 H 1.0772(18) -0.3079(14) 0.602(2) 0.081(6) Uiso 1 1 d . . .
H3 H 1.1598(17) -0.1515(14) 0.5828(19) 0.076(6) Uiso 1 1 d . . .
H4 H 1.0919(15) -0.0176(13) 0.6777(16) 0.059(5) Uiso 1 1 d . . .
H8 H 0.8247(13) 0.1238(11) 0.9498(15) 0.051(4) Uiso 1 1 d . . .
H9 H 0.6730(15) 0.0975(13) 1.0664(18) 0.066(5) Uiso 1 1 d . . .
H10 H 0.5900(17) -0.0593(13) 1.0753(19) 0.071(5) Uiso 1 1 d . . .
H11 H 0.6533(16) -0.1884(13) 0.9612(18) 0.070(5) Uiso 1 1 d . . .
H13 H 0.7878(14) -0.2548(11) 0.8348(15) 0.051(4) Uiso 1 1 d . . .
H15 H 1.0747(13) 0.0789(11) 0.8565(15) 0.046(4) Uiso 1 1 d . . .
H19 H 0.6684(15) 0.3213(11) 0.5349(16) 0.057(4) Uiso 1 1 d . . .
H20 H 0.7122(15) 0.4801(13) 0.4788(17) 0.064(5) Uiso 1 1 d . . .
H21 H 0.8997(14) 0.5450(12) 0.5593(16) 0.058(4) Uiso 1 1 d . . .
H22 H 1.0501(14) 0.4539(11) 0.6999(16) 0.054(4) Uiso 1 1 d . . .
H241 H 1.0497(15) 0.2829(13) 0.8748(18) 0.065(5) Uiso 1 1 d . . .
H242 H 1.0991(16) 0.2491(12) 0.7500(18) 0.067(5) 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 121.16(14) . . ?
C2 C1 H1 121.4(10) . . ?
C14 C1 H1 117.5(10) . . ?
C1 C2 C3 120.12(14) . . ?
C1 C2 H2 120.2(12) . . ?
C3 C2 H2 119.7(12) . . ?
C4 C3 C2 120.91(15) . . ?
C4 C3 H3 118.0(12) . . ?
C2 C3 H3 121.1(12) . . ?
C3 C4 C5 121.17(14) . . ?
C3 C4 H4 120.9(10) . . ?
C5 C4 H4 118.0(10) . . ?
C6 C5 C4 122.55(11) . . ?
C6 C5 C14 119.87(11) . . ?
C4 C5 C14 117.57(11) . . ?
C7 C6 C5 120.05(10) . . ?
C7 C6 C15 121.87(10) . . ?
C5 C6 C15 117.73(11) . . ?
C6 C7 C8 123.42(11) . . ?
C6 C7 C12 119.38(10) . . ?
C8 C7 C12 117.16(11) . . ?
C9 C8 C7 121.19(12) . . ?
C9 C8 H8 120.2(9) . . ?
C7 C8 H8 118.6(9) . . ?
C8 C9 C10 121.31(13) . . ?
C8 C9 H9 120.5(10) . . ?
C10 C9 H9 118.1(10) . . ?
C11 C10 C9 119.83(14) . . ?
C11 C10 H10 119.6(11) . . ?
C9 C10 H10 120.5(11) . . ?
C10 C11 C12 121.19(13) . . ?
C10 C11 H11 121.5(11) . . ?
C12 C11 H11 117.3(11) . . ?
C13 C12 C11 121.08(12) . . ?
C13 C12 C7 119.58(11) . . ?
C11 C12 C7 119.31(11) . . ?
C12 C13 C14 121.81(11) . . ?
C12 C13 H13 120.3(9) . . ?
C14 C13 H13 117.9(9) . . ?
C13 C14 C1 121.64(12) . . ?
C13 C14 C5 119.31(11) . . ?
C1 C14 C5 119.05(12) . . ?
C16 C15 C6 129.77(11) . . ?
C16 C15 H15 116.8(9) . . ?
C6 C15 H15 113.4(9) . . ?
C15 C16 C17 127.10(10) . . ?
C15 C16 C24 124.30(11) . . ?
C17 C16 C24 108.37(9) . . ?
O1 C17 C18 126.36(11) . . ?
O1 C17 C16 127.07(10) . . ?
C18 C17 C16 106.51(9) . . ?
C23 C18 C19 121.85(11) . . ?
C23 C18 C17 109.95(10) . . ?
C19 C18 C17 128.12(11) . . ?
C20 C19 C18 118.04(12) . . ?
C20 C19 H19 121.1(10) . . ?
C18 C19 H19 120.9(10) . . ?
C19 C20 C21 120.34(13) . . ?
C19 C20 H20 119.9(11) . . ?
C21 C20 H20 119.7(10) . . ?
C22 C21 C20 121.77(12) . . ?
C22 C21 H21 120.1(10) . . ?
C20 C21 H21 118.2(10) . . ?
C21 C22 C23 118.22(12) . . ?
C21 C22 H22 121.2(9) . . ?
C23 C22 H22 120.6(9) . . ?
C18 C23 C22 119.77(11) . . ?
C18 C23 C24 111.35(10) . . ?
C22 C23 C24 128.86(11) . . ?
C23 C24 C16 103.76(10) . . ?
C23 C24 H241 110.3(10) . . ?
C16 C24 H241 111.6(10) . . ?
C23 C24 H242 112.9(10) . . ?
C16 C24 H242 112.4(10) . . ?
H241 C24 H242 106.0(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 1.2192(13) . ?
C1 C2 1.351(2) . ?
C1 C14 1.4304(18) . ?
C1 H1 1.000(18) . ?
C2 C3 1.410(2) . ?
C2 H2 0.98(2) . ?
C3 C4 1.364(2) . ?
C3 H3 0.98(2) . ?
C4 C5 1.4280(18) . ?
C4 H4 0.978(18) . ?
C5 C6 1.4117(16) . ?
C5 C14 1.4330(16) . ?
C6 C7 1.4108(16) . ?
C6 C15 1.4790(16) . ?
C7 C8 1.4276(17) . ?
C7 C12 1.4383(16) . ?
C8 C9 1.358(2) . ?
C8 H8 1.006(16) . ?
C9 C10 1.415(2) . ?
C9 H9 1.005(18) . ?
C10 C11 1.346(2) . ?
C10 H10 0.994(19) . ?
C11 C12 1.4289(18) . ?
C11 H11 0.994(18) . ?
C12 C13 1.3888(18) . ?
C13 C14 1.389(2) . ?
C13 H13 0.993(16) . ?
C15 C16 1.3348(16) . ?
C15 H15 0.998(15) . ?
C16 C17 1.4944(16) . ?
C16 C24 1.5166(15) . ?
C17 C18 1.4752(15) . ?
C18 C23 1.3897(16) . ?
C18 C19 1.3928(17) . ?
C19 C20 1.3818(18) . ?
C19 H19 0.966(17) . ?
C20 C21 1.391(2) . ?
C20 H20 0.977(18) . ?
C21 C22 1.384(2) . ?
C21 H21 0.983(16) . ?
C22 C23 1.3949(16) . ?
C22 H22 0.984(16) . ?
C23 C24 1.5054(17) . ?
C24 H241 1.009(18) . ?
C24 H242 0.994(18) . ?
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(2) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C4 C5 C6 179.62(13) . . . . ?
C3 C4 C5 C14 -1.4(2) . . . . ?
C4 C5 C6 C7 178.92(11) . . . . ?
C14 C5 C6 C7 0.00(17) . . . . ?
C4 C5 C6 C15 -7.73(17) . . . . ?
C14 C5 C6 C15 173.35(11) . . . . ?
C5 C6 C7 C8 176.63(11) . . . . ?
C15 C6 C7 C8 3.56(17) . . . . ?
C5 C6 C7 C12 -0.90(16) . . . . ?
C15 C6 C7 C12 -173.97(11) . . . . ?
C6 C7 C8 C9 -177.97(13) . . . . ?
C12 C7 C8 C9 -0.38(19) . . . . ?
C7 C8 C9 C10 -0.6(2) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C13 176.91(15) . . . . ?
C10 C11 C12 C7 -1.0(2) . . . . ?
C6 C7 C12 C13 0.87(17) . . . . ?
C8 C7 C12 C13 -176.81(12) . . . . ?
C6 C7 C12 C11 178.83(12) . . . . ?
C8 C7 C12 C11 1.14(18) . . . . ?
C11 C12 C13 C14 -177.83(13) . . . . ?
C7 C12 C13 C14 0.1(2) . . . . ?
C12 C13 C14 C1 179.35(13) . . . . ?
C12 C13 C14 C5 -1.0(2) . . . . ?
C2 C1 C14 C13 178.75(14) . . . . ?
C2 C1 C14 C5 -0.9(2) . . . . ?
C6 C5 C14 C13 0.96(18) . . . . ?
C4 C5 C14 C13 -178.02(12) . . . . ?
C6 C5 C14 C1 -179.39(12) . . . . ?
C4 C5 C14 C1 1.64(18) . . . . ?
C7 C6 C15 C16 -62.91(18) . . . . ?
C5 C6 C15 C16 123.87(14) . . . . ?
C6 C15 C16 C17 -7.6(2) . . . . ?
C6 C15 C16 C24 178.49(12) . . . . ?
C15 C16 C17 O1 4.0(2) . . . . ?
C24 C16 C17 O1 178.62(12) . . . . ?
C15 C16 C17 C18 -173.31(12) . . . . ?
C24 C16 C17 C18 1.36(13) . . . . ?
O1 C17 C18 C23 -177.08(12) . . . . ?
C16 C17 C18 C23 0.21(12) . . . . ?
O1 C17 C18 C19 -0.3(2) . . . . ?
C16 C17 C18 C19 176.96(12) . . . . ?
C23 C18 C19 C20 0.76(19) . . . . ?
C17 C18 C19 C20 -175.64(12) . . . . ?
C18 C19 C20 C21 -0.4(2) . . . . ?
C19 C20 C21 C22 -0.4(2) . . . . ?
C20 C21 C22 C23 0.9(2) . . . . ?
C19 C18 C23 C22 -0.34(17) . . . . ?
C17 C18 C23 C22 176.65(10) . . . . ?
C19 C18 C23 C24 -178.73(11) . . . . ?
C17 C18 C23 C24 -1.74(14) . . . . ?
C21 C22 C23 C18 -0.47(18) . . . . ?
C21 C22 C23 C24 177.61(13) . . . . ?
C18 C23 C24 C16 2.49(14) . . . . ?
C22 C23 C24 C16 -175.72(12) . . . . ?
C15 C16 C24 C23 172.58(12) . . . . ?
C17 C16 C24 C23 -2.27(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21188683
