#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:08:27 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178422 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/43/4024344.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_4024344
loop_
_publ_author_name
'Manon Chaumontet'
'Pascal Retailleau'
'Olivier Baudoin'
_publ_contact_author_address
;
ICSN-CNRS
1 avenue de la Terrasse
91198 Gif sur Yvette
France

;
_publ_contact_author_email       @icsn.cnrs-gif.fr
_publ_contact_author_fax         33169077247
_publ_contact_author_phone       3316982
_publ_section_title
;
Cycloadditions of 1,1-Disubstituted Benzocyclobutenes Obtained by
C(sp3)-H Activation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1774
_journal_page_last               1776
_journal_paper_doi               10.1021/jo802471u
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H16 F3 N O4'
_chemical_formula_sum            'C17 H16 F3 N O4'
_chemical_formula_weight         355.31
_chemical_name_systematic
; 
 methyl 2,4-dimethyl-1,3-dioxo-7-(trifluoromethyl)-2,3,3a,4,9,9a-
 hexahydro-1H-benzo[f]isoindole-4-carboxylate 
;
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             29-09-08
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   25.902(4)
_cell_length_b                   28.819(4)
_cell_length_c                   8.794(2)
_cell_measurement_temperature    293(2)
_cell_volume                     6564(2)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)'
_computing_data_reduction        'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement
'SHELXL97 (Sheldrick, 2008); CRYSTALBUILDER (Welter, 2006)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3265
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.11
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Nonius Kappa CCD'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2944
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0020(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   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         1785
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0553P)²+2.6474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0957
_reflns_number_gt                1473
_reflns_number_total             1785
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802471u_si_001.cif
_cod_data_source_block           mc808a
_cod_original_sg_symbol_H-M      Fdd2
_cod_database_code               4024344
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'
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
F1 F 0.55651(8) 0.11014(7) -0.0999(3) 0.0896(7) Uani 1 1 d . . .
F2 F 0.57449(8) 0.04982(10) 0.0241(4) 0.1165(11) Uani 1 1 d . . .
F3 F 0.54684(10) 0.04424(11) -0.2010(4) 0.1210(11) Uani 1 1 d . . .
O1 O 0.28624(8) 0.01689(7) 0.3129(3) 0.0639(6) Uani 1 1 d . . .
O2 O 0.31839(8) -0.00728(7) 0.0917(3) 0.0643(6) Uani 1 1 d . . .
O3 O 0.33074(10) 0.17918(7) 0.1766(3) 0.0728(7) Uani 1 1 d . . .
O4 O 0.43725(9) 0.13017(8) 0.5506(3) 0.0643(6) Uani 1 1 d . . .
N1 N 0.38790(8) 0.16391(7) 0.3660(3) 0.0449(5) Uani 1 1 d . . .
C1 C 0.42485(9) 0.05795(8) 0.1860(3) 0.0369(6) Uani 1 1 d . . .
C2 C 0.47565(10) 0.05738(8) 0.1362(3) 0.0420(6) Uani 1 1 d . . .
H2 H 0.5024 0.0515 0.2042 0.050 Uiso 1 1 calc R . .
C3 C 0.48622(11) 0.06560(9) -0.0157(4) 0.0483(7) Uani 1 1 d . . .
C4 C 0.44677(12) 0.07468(10) -0.1177(3) 0.0538(7) Uani 1 1 d . . .
H4 H 0.4542 0.0798 -0.2198 0.065 Uiso 1 1 calc R . .
C5 C 0.39640(11) 0.07607(10) -0.0675(3) 0.0490(7) Uani 1 1 d . . .
H5 H 0.3699 0.0822 -0.1359 0.059 Uiso 1 1 calc R . .
C6 C 0.38500(9) 0.06834(8) 0.0848(3) 0.0382(6) Uani 1 1 d . . .
C7 C 0.54052(13) 0.06729(11) -0.0713(4) 0.0638(9) Uani 1 1 d . . .
C8 C 0.33071(9) 0.07193(8) 0.1498(3) 0.0410(6) Uani 1 1 d . . .
C9 C 0.30965(10) 0.02434(9) 0.1972(3) 0.0451(6) Uani 1 1 d . . .
C10 C 0.29770(16) -0.05309(11) 0.1198(5) 0.0839(12) Uani 1 1 d . . .
H10A H 0.3160 -0.0672 0.2026 0.126 Uiso 1 1 calc R . .
H10B H 0.3016 -0.0718 0.0301 0.126 Uiso 1 1 calc R . .
H10C H 0.2618 -0.0507 0.1452 0.126 Uiso 1 1 calc R . .
C11 C 0.29070(10) 0.09114(11) 0.0358(4) 0.0568(8) Uani 1 1 d . . .
H11A H 0.3031 0.1198 -0.0063 0.085 Uiso 1 1 calc R . .
H11B H 0.2586 0.0966 0.0874 0.085 Uiso 1 1 calc R . .
H11C H 0.2855 0.0690 -0.0444 0.085 Uiso 1 1 calc R . .
C12 C 0.33362(9) 0.10173(8) 0.2952(3) 0.0425(6) Uani 1 1 d . . .
H12 H 0.2996 0.1015 0.3437 0.051 Uiso 1 1 calc R . .
C13 C 0.37359(11) 0.08482(8) 0.4120(3) 0.0423(6) Uani 1 1 d . . .
H13 H 0.3558 0.0725 0.5017 0.051 Uiso 1 1 calc R . .
C14 C 0.41123(10) 0.04790(9) 0.3493(3) 0.0418(6) Uani 1 1 d . . .
H14A H 0.4424 0.0477 0.4103 0.050 Uiso 1 1 calc R . .
H14B H 0.3954 0.0175 0.3563 0.050 Uiso 1 1 calc R . .
C15 C 0.34909(10) 0.15215(10) 0.2670(3) 0.0470(6) Uani 1 1 d . . .
C16 C 0.40375(11) 0.12768(9) 0.4556(3) 0.0439(6) Uani 1 1 d . . .
C17 C 0.40794(12) 0.21098(10) 0.3823(4) 0.0588(8) Uani 1 1 d . . .
H17A H 0.4250 0.2200 0.2901 0.088 Uiso 1 1 calc R . .
H17B H 0.4320 0.2120 0.4651 0.088 Uiso 1 1 calc R . .
H17C H 0.3799 0.2319 0.4023 0.088 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O2 C10 116.5(3) . . ?
C16 N1 C15 113.3(2) . . ?
C16 N1 C17 123.0(2) . . ?
C15 N1 C17 123.5(2) . . ?
C2 C1 C6 120.2(2) . . ?
C2 C1 C14 121.4(2) . . ?
C6 C1 C14 118.4(2) . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 C7 120.6(3) . . ?
C4 C3 C7 118.6(3) . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 119.5(2) . . ?
C5 C6 C8 123.2(2) . . ?
C1 C6 C8 117.3(2) . . ?
F2 C7 F1 105.6(3) . . ?
F2 C7 F3 105.9(3) . . ?
F1 C7 F3 105.3(3) . . ?
F2 C7 C3 114.2(3) . . ?
F1 C7 C3 112.8(2) . . ?
F3 C7 C3 112.4(3) . . ?
C6 C8 C9 111.7(2) . . ?
C6 C8 C12 107.7(2) . . ?
C9 C8 C12 106.9(2) . . ?
C6 C8 C11 113.6(2) . . ?
C9 C8 C11 105.0(2) . . ?
C12 C8 C11 111.8(2) . . ?
O1 C9 O2 123.9(3) . . ?
O1 C9 C8 124.6(3) . . ?
O2 C9 C8 111.4(2) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C15 C12 C13 103.5(2) . . ?
C15 C12 C8 114.1(2) . . ?
C13 C12 C8 114.2(2) . . ?
C15 C12 H12 108.3 . . ?
C13 C12 H12 108.3 . . ?
C8 C12 H12 108.3 . . ?
C16 C13 C12 105.0(2) . . ?
C16 C13 C14 109.1(2) . . ?
C12 C13 C14 113.9(2) . . ?
C16 C13 H13 109.6 . . ?
C12 C13 H13 109.6 . . ?
C14 C13 H13 109.6 . . ?
C1 C14 C13 110.8(2) . . ?
C1 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C1 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
O3 C15 N1 123.1(3) . . ?
O3 C15 C12 128.0(3) . . ?
N1 C15 C12 108.9(2) . . ?
O4 C16 N1 124.6(3) . . ?
O4 C16 C13 126.6(2) . . ?
N1 C16 C13 108.8(2) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
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
F1 C7 1.327(3) . ?
F2 C7 1.315(5) . ?
F3 C7 1.331(5) . ?
O1 C9 1.204(4) . ?
O2 C9 1.319(4) . ?
O2 C10 1.446(4) . ?
O3 C15 1.210(3) . ?
O4 C16 1.207(3) . ?
N1 C16 1.371(4) . ?
N1 C15 1.372(4) . ?
N1 C17 1.460(3) . ?
C1 C2 1.387(4) . ?
C1 C6 1.395(4) . ?
C1 C14 1.506(4) . ?
C2 C3 1.384(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(4) . ?
C3 C7 1.490(4) . ?
C4 C5 1.378(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(4) . ?
C5 H5 0.9300 . ?
C6 C8 1.521(3) . ?
C8 C9 1.534(4) . ?
C8 C12 1.542(4) . ?
C8 C11 1.544(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C15 1.528(4) . ?
C12 C13 1.538(4) . ?
C12 H12 0.9800 . ?
C13 C16 1.511(4) . ?
C13 C14 1.545(3) . ?
C13 H13 0.9800 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
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
C6 C1 C2 C3 -2.2(4) . . . . ?
C14 C1 C2 C3 178.3(2) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C1 C2 C3 C7 177.3(2) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C7 C3 C4 C5 -176.1(3) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C1 -1.6(4) . . . . ?
C4 C5 C6 C8 176.6(2) . . . . ?
C2 C1 C6 C5 2.8(4) . . . . ?
C14 C1 C6 C5 -177.7(2) . . . . ?
C2 C1 C6 C8 -175.5(2) . . . . ?
C14 C1 C6 C8 4.0(3) . . . . ?
C2 C3 C7 F2 15.4(4) . . . . ?
C4 C3 C7 F2 -167.7(3) . . . . ?
C2 C3 C7 F1 -105.1(4) . . . . ?
C4 C3 C7 F1 71.7(4) . . . . ?
C2 C3 C7 F3 136.0(3) . . . . ?
C4 C3 C7 F3 -47.1(4) . . . . ?
C5 C6 C8 C9 111.0(3) . . . . ?
C1 C6 C8 C9 -70.8(3) . . . . ?
C5 C6 C8 C12 -132.0(3) . . . . ?
C1 C6 C8 C12 46.3(3) . . . . ?
C5 C6 C8 C11 -7.5(4) . . . . ?
C1 C6 C8 C11 170.7(2) . . . . ?
C10 O2 C9 O1 0.6(5) . . . . ?
C10 O2 C9 C8 -176.6(3) . . . . ?
C6 C8 C9 O1 137.2(3) . . . . ?
C12 C8 C9 O1 19.6(3) . . . . ?
C11 C8 C9 O1 -99.3(3) . . . . ?
C6 C8 C9 O2 -45.6(3) . . . . ?
C12 C8 C9 O2 -163.2(2) . . . . ?
C11 C8 C9 O2 77.9(3) . . . . ?
C6 C8 C12 C15 65.3(3) . . . . ?
C9 C8 C12 C15 -174.5(2) . . . . ?
C11 C8 C12 C15 -60.2(3) . . . . ?
C6 C8 C12 C13 -53.4(3) . . . . ?
C9 C8 C12 C13 66.7(3) . . . . ?
C11 C8 C12 C13 -178.9(2) . . . . ?
C15 C12 C13 C16 7.0(3) . . . . ?
C8 C12 C13 C16 131.6(2) . . . . ?
C15 C12 C13 C14 -112.3(2) . . . . ?
C8 C12 C13 C14 12.3(3) . . . . ?
C2 C1 C14 C13 132.1(2) . . . . ?
C6 C1 C14 C13 -47.4(3) . . . . ?
C16 C13 C14 C1 -80.0(3) . . . . ?
C12 C13 C14 C1 36.8(3) . . . . ?
C16 N1 C15 O3 -178.5(3) . . . . ?
C17 N1 C15 O3 5.6(4) . . . . ?
C16 N1 C15 C12 3.1(3) . . . . ?
C17 N1 C15 C12 -172.8(2) . . . . ?
C13 C12 C15 O3 175.3(3) . . . . ?
C8 C12 C15 O3 50.6(4) . . . . ?
C13 C12 C15 N1 -6.3(3) . . . . ?
C8 C12 C15 N1 -131.0(2) . . . . ?
C15 N1 C16 O4 -179.9(2) . . . . ?
C17 N1 C16 O4 -4.0(4) . . . . ?
C15 N1 C16 C13 1.7(3) . . . . ?
C17 N1 C16 C13 177.6(2) . . . . ?
C12 C13 C16 O4 176.0(3) . . . . ?
C14 C13 C16 O4 -61.6(3) . . . . ?
C12 C13 C16 N1 -5.6(3) . . . . ?
C14 C13 C16 N1 116.7(2) . . . . ?
