#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:23:00 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/88/4028867.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_4028867
loop_
_publ_author_name
'Naoki Kise'
'Yusuke Kawano'
'Toshihiko Sakurai'
_publ_section_title
;
 Reductive Coupling of Phthalimides with Ketones and Aldehydes by
 Low-Valent Titanium: One-Pot Synthesis of Alkylideneisoindolin-1-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              12453
_journal_page_last               12459
_journal_paper_doi               10.1021/jo402125u
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C16 H12 F N O'
_chemical_formula_sum            'C16 H12 F N O'
_chemical_formula_weight         253.27
_chemical_melting_point          429(1)
_chemical_name_systematic
; 
(E)-3-(4-fluorobenzylidene)-2-methylisoindolin-1-one 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 93.012(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5792(7)
_cell_length_b                   11.4148(9)
_cell_length_c                   11.4639(7)
_cell_measurement_temperature    298(2)
_cell_volume                     1251.78(15)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_publication_material  yadokari-XG
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11797
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.36
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9633
_exptl_absorpt_correction_T_min  0.9544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
    Higashi, T. (1995). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0393
_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)+(0.0631P)²+0.0644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1108
_reflns_number_gt                2222
_reflns_number_total             2838
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo402125u_si_008.cif
_cod_data_source_block           E-7j
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4028867
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
N1 N 0.47982(10) 0.22712(8) -0.03346(8) 0.0507(2) Uani 1 1 d .
C1 C 0.56471(15) 0.32924(11) -0.00548(12) 0.0671(4) Uani 1 1 d .
H1 H 0.6471 0.3274 -0.0497 0.101 Uiso 1 1 calc R
H2 H 0.5913 0.3292 0.0764 0.101 Uiso 1 1 calc R
H3 H 0.5121 0.3988 -0.0247 0.101 Uiso 1 1 calc R
C2 C 0.50954(12) 0.14984(10) -0.12057(9) 0.0490(3) Uani 1 1 d .
O1 O 0.60627(10) 0.15880(8) -0.18620(7) 0.0648(3) Uani 1 1 d .
C3 C 0.40184(11) 0.05779(9) -0.11768(9) 0.0457(3) Uani 1 1 d .
C4 C 0.38120(12) -0.03830(11) -0.19001(9) 0.0536(3) Uani 1 1 d .
H4 H 0.4417 -0.0539 -0.2489 0.064 Uiso 1 1 calc R
C5 C 0.26861(13) -0.11037(11) -0.17257(11) 0.0591(3) Uani 1 1 d .
H5 H 0.2531 -0.1759 -0.2197 0.071 Uiso 1 1 calc R
C6 C 0.17832(13) -0.08556(11) -0.08498(11) 0.0573(3) Uani 1 1 d .
H6 H 0.1019 -0.1342 -0.0754 0.069 Uiso 1 1 calc R
C7 C 0.19942(11) 0.01005(10) -0.01142(9) 0.0507(3) Uani 1 1 d .
H7 H 0.1384 0.0256 0.0472 0.061 Uiso 1 1 calc R
C8 C 0.31396(10) 0.08210(9) -0.02736(8) 0.0430(2) Uani 1 1 d .
C9 C 0.36430(11) 0.19113(10) 0.02974(9) 0.0458(3) Uani 1 1 d .
C10 C 0.31829(13) 0.25298(11) 0.11953(10) 0.0538(3) Uani 1 1 d .
H8 H 0.3582 0.3266 0.1316 0.065 Uiso 1 1 calc R
C11 C 0.21224(12) 0.21835(10) 0.20129(9) 0.0516(3) Uani 1 1 d .
C12 C 0.11046(14) 0.29863(12) 0.23228(11) 0.0619(3) Uani 1 1 d .
H9 H 0.1073 0.3723 0.1976 0.074 Uiso 1 1 calc R
C13 C 0.01422(14) 0.27043(14) 0.31379(12) 0.0702(4) Uani 1 1 d .
H10 H -0.0548 0.3234 0.3326 0.084 Uiso 1 1 calc R
C14 C 0.02307(14) 0.16325(15) 0.36576(11) 0.0693(4) Uani 1 1 d .
F1 F -0.07109(10) 0.13552(11) 0.44661(8) 0.1043(4) Uani 1 1 d .
C15 C 0.12167(14) 0.08127(14) 0.33986(11) 0.0692(4) Uani 1 1 d .
H11 H 0.1248 0.0088 0.3769 0.083 Uiso 1 1 calc R
C16 C 0.21637(13) 0.10960(13) 0.25693(10) 0.0600(3) Uani 1 1 d .
H12 H 0.2838 0.0552 0.2381 0.072 Uiso 1 1 calc R
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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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
C2 N1 C9 112.54(9)
C2 N1 C1 122.88(10)
C9 N1 C1 124.45(10)
N1 C1 H1 109.5
N1 C1 H2 109.5
H1 C1 H2 109.5
N1 C1 H3 109.5
H1 C1 H3 109.5
H2 C1 H3 109.5
O1 C2 N1 125.72(11)
O1 C2 C3 128.65(11)
N1 C2 C3 105.63(9)
C4 C3 C8 121.97(10)
C4 C3 C2 129.06(10)
C8 C3 C2 108.96(9)
C5 C4 C3 118.32(10)
C5 C4 H4 120.8
C3 C4 H4 120.8
C4 C5 C6 120.31(11)
C4 C5 H5 119.8
C6 C5 H5 119.8
C7 C6 C5 121.58(12)
C7 C6 H6 119.2
C5 C6 H6 119.2
C6 C7 C8 118.42(10)
C6 C7 H7 120.8
C8 C7 H7 120.8
C7 C8 C3 119.36(10)
C7 C8 C9 133.02(10)
C3 C8 C9 107.52(9)
C10 C9 N1 122.50(10)
C10 C9 C8 132.18(10)
N1 C9 C8 105.30(9)
C9 C10 C11 127.79(11)
C9 C10 H8 116.1
C11 C10 H8 116.1
C16 C11 C12 118.07(12)
C16 C11 C10 121.74(11)
C12 C11 C10 119.99(11)
C13 C12 C11 121.15(13)
C13 C12 H9 119.4
C11 C12 H9 119.4
C14 C13 C12 118.41(13)
C14 C13 H10 120.8
C12 C13 H10 120.8
C13 C14 F1 118.53(13)
C13 C14 C15 123.06(13)
F1 C14 C15 118.41(15)
C14 C15 C16 118.14(14)
C14 C15 H11 120.9
C16 C15 H11 120.9
C15 C16 C11 121.14(12)
C15 C16 H12 119.4
C11 C16 H12 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.3735(14)
N1 C9 1.4151(14)
N1 C1 1.4476(15)
C1 H1 0.9600
C1 H2 0.9600
C1 H3 0.9600
C2 O1 1.2282(14)
C2 C3 1.4741(16)
C3 C4 1.3829(15)
C3 C8 1.3963(14)
C4 C5 1.3793(17)
C4 H4 0.9300
C5 C6 1.3884(18)
C5 H5 0.9300
C6 C7 1.3875(16)
C6 H6 0.9300
C7 C8 1.3910(15)
C7 H7 0.9300
C8 C9 1.4753(15)
C9 C10 1.3416(15)
C10 C11 1.4721(17)
C10 H8 0.9300
C11 C16 1.3952(18)
C11 C12 1.3974(16)
C12 C13 1.3847(19)
C12 H9 0.9300
C13 C14 1.362(2)
C13 H10 0.9300
C14 F1 1.3640(16)
C14 C15 1.373(2)
C15 C16 1.3863(17)
C15 H11 0.9300
C16 H12 0.9300
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
C9 N1 C2 O1 -178.15(10)
C1 N1 C2 O1 -2.25(18)
C9 N1 C2 C3 2.29(11)
C1 N1 C2 C3 178.19(10)
O1 C2 C3 C4 -2.17(19)
N1 C2 C3 C4 177.37(11)
O1 C2 C3 C8 179.10(11)
N1 C2 C3 C8 -1.36(11)
C8 C3 C4 C5 1.11(16)
C2 C3 C4 C5 -177.47(11)
C3 C4 C5 C6 0.56(17)
C4 C5 C6 C7 -1.26(19)
C5 C6 C7 C8 0.27(18)
C6 C7 C8 C3 1.35(15)
C6 C7 C8 C9 177.13(11)
C4 C3 C8 C7 -2.09(15)
C2 C3 C8 C7 176.75(9)
C4 C3 C8 C9 -178.85(9)
C2 C3 C8 C9 -0.01(11)
C2 N1 C9 C10 179.21(11)
C1 N1 C9 C10 3.38(17)
C2 N1 C9 C8 -2.31(11)
C1 N1 C9 C8 -178.13(10)
C7 C8 C9 C10 3.5(2)
C3 C8 C9 C10 179.61(12)
C7 C8 C9 N1 -174.80(11)
C3 C8 C9 N1 1.33(11)
N1 C9 C10 C11 -171.47(11)
C8 C9 C10 C11 10.5(2)
C9 C10 C11 C16 48.84(17)
C9 C10 C11 C12 -136.38(13)
C16 C11 C12 C13 -1.49(18)
C10 C11 C12 C13 -176.45(11)
C11 C12 C13 C14 1.69(19)
C12 C13 C14 F1 179.61(11)
C12 C13 C14 C15 -1.0(2)
C13 C14 C15 C16 0.1(2)
F1 C14 C15 C16 179.48(11)
C14 C15 C16 C11 0.15(19)
C12 C11 C16 C15 0.55(18)
C10 C11 C16 C15 175.43(11)
