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#$Date: 2016-03-21 03:01:04 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178416 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/37/4023784.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_4023784
loop_
_publ_author_name
'Ronald Grigg'
'Visuvanathar Sridharan'
'Mufakhrul Shah'
'Simon Mutton'
'Colin Kilner'
'David MacPherson'
'Peter Milner'
_publ_section_title
;
 Regioselective Synthesis of N-Aminoisoindolones and Mono-N-
 and Di-N,N'-substituted Phthalazones Utilizing Hydrazine Nucleophiles
 in a Palladium-Catalyzed Three-Component Cascade Process
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8352
_journal_page_last               8356
_journal_paper_doi               10.1021/jo800822p
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C12 H10 F3 N3 O'
_chemical_formula_weight         269.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                111.4460(12)
_cell_angle_beta                 90.2980(12)
_cell_angle_gamma                103.1660(18)
_cell_formula_units_Z            2
_cell_length_a                   6.8280(2)
_cell_length_b                   8.5650(2)
_cell_length_c                   11.4050(4)
_cell_measurement_temperature    150(2)
_cell_volume                     601.60(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0736
_diffrn_reflns_av_sigmaI/netI    0.0457
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12103
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.47
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_correction_T_min  0.9720
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2358
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0405
_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)+(0.0613P)²+0.0685P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1121
_reflns_number_gt                1869
_reflns_number_total             2358
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800822p_si_002.cif
_cod_data_source_block           ms143
_cod_database_code               4023784
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
F15 F 0.04473(15) 0.10498(14) 0.21314(9) 0.0516(3) Uani 1 1 d . . .
F16 F 0.35022(15) 0.21346(13) 0.18729(9) 0.0490(3) Uani 1 1 d . . .
N1 N 0.17144(18) 0.33722(16) 0.60160(11) 0.0273(3) Uani 1 1 d . . .
O91 O 0.20584(16) 0.62395(14) 0.63418(10) 0.0344(3) Uani 1 1 d . . .
N11 N 0.10279(19) 0.26353(17) 0.47231(11) 0.0287(3) Uani 1 1 d . . .
H11 H -0.006(3) 0.301(2) 0.4623(16) 0.034 Uiso 1 1 d . . .
F14 F 0.28967(17) 0.03329(13) 0.28110(10) 0.0541(3) Uani 1 1 d . . .
N23 N 0.6703(2) 0.27494(18) 0.63546(13) 0.0372(3) Uani 1 1 d . . .
C22 C 0.5076(2) 0.20016(19) 0.63488(13) 0.0291(3) Uani 1 1 d . . .
C2 C 0.1554(2) 0.22473(19) 0.67335(14) 0.0282(3) Uani 1 1 d . . .
H2 H 0.0133 0.1536 0.6611 0.034 Uiso 1 1 calc R . .
C8 C 0.2258(2) 0.5215(2) 0.80743(14) 0.0283(3) Uani 1 1 d . . .
C7 C 0.2606(2) 0.6668(2) 0.91886(14) 0.0325(4) Uani 1 1 d . . .
H7 H 0.2753 0.7794 0.9180 0.039 Uiso 1 1 calc R . .
C9 C 0.2010(2) 0.5092(2) 0.67496(14) 0.0283(3) Uani 1 1 d . . .
C6 C 0.2729(2) 0.6411(2) 1.03185(14) 0.0354(4) Uani 1 1 d . . .
H6 H 0.2964 0.7377 1.1099 0.042 Uiso 1 1 calc R . .
C12 C 0.2532(2) 0.3157(2) 0.39343(14) 0.0317(4) Uani 1 1 d . . .
H12A H 0.3909 0.3471 0.4364 0.038 Uiso 1 1 calc R . .
H12B H 0.2301 0.4178 0.3795 0.038 Uiso 1 1 calc R . .
C4 C 0.2156(2) 0.3315(2) 0.92061(14) 0.0322(4) Uani 1 1 d . . .
H4 H 0.2015 0.2190 0.9215 0.039 Uiso 1 1 calc R . .
C3 C 0.2013(2) 0.3560(2) 0.80761(14) 0.0277(3) Uani 1 1 d . . .
C21 C 0.2993(2) 0.1044(2) 0.63139(15) 0.0307(4) Uani 1 1 d . . .
H21A H 0.2951 0.0391 0.6876 0.037 Uiso 1 1 calc R . .
H21B H 0.2527 0.0198 0.5442 0.037 Uiso 1 1 calc R . .
C5 C 0.2513(2) 0.4763(2) 1.03239(14) 0.0349(4) Uani 1 1 d . . .
H5 H 0.2611 0.4623 1.1109 0.042 Uiso 1 1 calc R . .
C13 C 0.2339(2) 0.1676(2) 0.26945(15) 0.0342(4) Uani 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 N11 124.26(12) . . ?
C9 N1 C2 114.25(12) . . ?
N11 N1 C2 119.00(12) . . ?
N1 N11 C12 112.75(11) . . ?
N1 N11 H11 107.7(11) . . ?
C12 N11 H11 107.6(11) . . ?
N23 C22 C21 178.80(15) . . ?
N1 C2 C3 101.35(12) . . ?
N1 C2 C21 111.37(12) . . ?
C3 C2 C21 115.39(12) . . ?
N1 C2 H2 109.5 . . ?
C3 C2 H2 109.5 . . ?
C21 C2 H2 109.5 . . ?
C7 C8 C3 121.86(14) . . ?
C7 C8 C9 129.19(14) . . ?
C3 C8 C9 108.92(13) . . ?
C8 C7 C6 117.33(15) . . ?
C8 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
O91 C9 N1 124.87(14) . . ?
O91 C9 C8 129.54(14) . . ?
N1 C9 C8 105.58(13) . . ?
C5 C6 C7 120.99(15) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
N11 C12 C13 108.61(12) . . ?
N11 C12 H12A 110.0 . . ?
C13 C12 H12A 110.0 . . ?
N11 C12 H12B 110.0 . . ?
C13 C12 H12B 110.0 . . ?
H12A C12 H12B 108.3 . . ?
C3 C4 C5 117.94(15) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C4 C3 C8 120.48(14) . . ?
C4 C3 C2 129.88(14) . . ?
C8 C3 C2 109.62(12) . . ?
C22 C21 C2 112.08(12) . . ?
C22 C21 H21A 109.2 . . ?
C2 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
C2 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C6 C5 C4 121.38(14) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
F15 C13 F14 105.97(13) . . ?
F15 C13 F16 106.75(13) . . ?
F14 C13 F16 106.53(12) . . ?
F15 C13 C12 113.10(13) . . ?
F14 C13 C12 112.46(13) . . ?
F16 C13 C12 111.58(13) . . ?
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
F15 C13 1.3387(19) . ?
F16 C13 1.3408(17) . ?
N1 C9 1.368(2) . ?
N1 N11 1.4036(17) . ?
N1 C2 1.4627(19) . ?
O91 C9 1.2263(18) . ?
N11 C12 1.4691(18) . ?
N11 H11 0.895(17) . ?
F14 C13 1.3407(18) . ?
N23 C22 1.148(2) . ?
C22 C21 1.463(2) . ?
C2 C3 1.511(2) . ?
C2 C21 1.536(2) . ?
C2 H2 1.0000 . ?
C8 C7 1.388(2) . ?
C8 C3 1.390(2) . ?
C8 C9 1.481(2) . ?
C7 C6 1.390(2) . ?
C7 H7 0.9500 . ?
C6 C5 1.388(2) . ?
C6 H6 0.9500 . ?
C12 C13 1.495(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C4 C3 1.386(2) . ?
C4 C5 1.388(2) . ?
C4 H4 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C5 H5 0.9500 . ?
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
C9 N1 N11 C12 69.81(17) . . . . ?
C2 N1 N11 C12 -129.16(13) . . . . ?
C9 N1 C2 C3 -5.55(15) . . . . ?
N11 N1 C2 C3 -168.42(11) . . . . ?
C9 N1 C2 C21 -128.79(13) . . . . ?
N11 N1 C2 C21 68.34(16) . . . . ?
C3 C8 C7 C6 0.9(2) . . . . ?
C9 C8 C7 C6 178.39(13) . . . . ?
N11 N1 C9 O91 -13.4(2) . . . . ?
C2 N1 C9 O91 -175.21(13) . . . . ?
N11 N1 C9 C8 167.07(12) . . . . ?
C2 N1 C9 C8 5.23(16) . . . . ?
C7 C8 C9 O91 0.1(2) . . . . ?
C3 C8 C9 O91 177.91(14) . . . . ?
C7 C8 C9 N1 179.67(14) . . . . ?
C3 C8 C9 N1 -2.57(15) . . . . ?
C8 C7 C6 C5 0.0(2) . . . . ?
N1 N11 C12 C13 145.95(13) . . . . ?
C5 C4 C3 C8 1.1(2) . . . . ?
C5 C4 C3 C2 -177.17(14) . . . . ?
C7 C8 C3 C4 -1.5(2) . . . . ?
C9 C8 C3 C4 -179.46(12) . . . . ?
C7 C8 C3 C2 177.13(13) . . . . ?
C9 C8 C3 C2 -0.83(15) . . . . ?
N1 C2 C3 C4 -177.92(13) . . . . ?
C21 C2 C3 C4 -57.5(2) . . . . ?
N1 C2 C3 C8 3.62(15) . . . . ?
C21 C2 C3 C8 124.06(13) . . . . ?
N23 C22 C21 C2 -91(7) . . . . ?
N1 C2 C21 C22 53.03(17) . . . . ?
C3 C2 C21 C22 -61.78(17) . . . . ?
C7 C6 C5 C4 -0.3(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
N11 C12 C13 F15 52.14(17) . . . . ?
N11 C12 C13 F14 -67.85(16) . . . . ?
N11 C12 C13 F16 172.52(13) . . . . ?
