#------------------------------------------------------------------------------
#$Date: 2022-09-27 00:53:41 +0300 (Tue, 27 Sep 2022) $
#$Revision: 278195 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/07/7130771.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_7130771
loop_
_publ_author_name
'Rkein, Batoul'
'Coffinier, Romain'
'Powderly, Marian'
'Manneveau, Maxime'
'Sanselme, Morgane'
'Durandetti, Muriel'
'Sebban, Muriel'
'Hamdoun, Ghanem'
'Oulyadi, Hassan'
'Harrowven, David'
'Legros, Julien'
'Chataigner, Isabelle'
_publ_section_title
;
 High Pressure promoted Dearomatization of Nitroarenes by [4+2]
 Cycloadditions with Silyloxydienes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04778K
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C14 H13 F1 N2 O4'
_chemical_formula_sum            'C14 H13 F N2 O4'
_chemical_formula_weight         292.26
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2021-06-10T16:01:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2022-08-08 deposited with the CCDC.	2022-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0454(12)
_cell_length_b                   10.7142(12)
_cell_length_c                   12.3095(14)
_cell_measurement_reflns_used    1565
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.26
_cell_measurement_theta_min      2.52
_cell_measurement_wavelength     0.71073
_cell_volume                     1324.9(3)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'SMART APEX I Bruker'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5937
_diffrn_reflns_theta_full        23.26
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1901
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0516P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0968
_reflns_number_gt                1565
_reflns_number_total             1901
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            d2cc04778k2.cif
_cod_data_source_block           mp46a
_cod_database_code               7130771
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0743(3) 0.9368(3) 0.1979(3) 0.0539(8) Uani 1 1 d . . .
H1 H -0.1509 0.9029 0.2284 0.065 Uiso 1 1 calc R . .
C2 C -0.0460(3) 1.0590(3) 0.2190(2) 0.0509(8) Uani 1 1 d . . .
H2 H -0.1 1.1055 0.2653 0.061 Uiso 1 1 calc R . .
C3 C 0.0640(3) 1.1125(3) 0.1706(2) 0.0433(7) Uani 1 1 d . . .
H3 H 0.0835 1.1964 0.182 0.052 Uiso 1 1 calc R . .
C4 C 0.1451(2) 1.0403(2) 0.1048(2) 0.0353(6) Uani 1 1 d . . .
C5 C 0.2651(2) 1.0876(2) 0.0423(2) 0.0361(7) Uani 1 1 d . . .
C6 C 0.3739(2) 0.9886(3) 0.0330(2) 0.0438(7) Uani 1 1 d . . .
H6 H 0.4393 1.0163 -0.0209 0.053 Uiso 1 1 calc R . .
C7 C 0.3169(3) 0.8655(3) -0.0033(3) 0.0527(8) Uani 1 1 d . . .
H7 H 0.367 0.8118 -0.0463 0.063 Uiso 1 1 calc R . .
C8 C 0.1966(3) 0.8350(2) 0.0262(3) 0.0540(8) Uani 1 1 d . . .
C9 C 0.1091(3) 0.9146(3) 0.0917(2) 0.0425(7) Uani 1 1 d . . .
C10 C 0.3266(3) 1.2110(3) 0.0811(2) 0.0458(7) Uani 1 1 d . . .
H10 H 0.3982 1.2333 0.0306 0.055 Uiso 1 1 calc R . .
C11 C 0.3877(3) 1.1956(3) 0.1934(2) 0.0606(9) Uani 1 1 d . . .
H11A H 0.4304 1.273 0.2147 0.073 Uiso 1 1 calc R . .
H11B H 0.3179 1.1777 0.2456 0.073 Uiso 1 1 calc R . .
C12 C 0.4885(3) 1.0918(4) 0.1953(3) 0.0648(10) Uani 1 1 d . . .
C13 C 0.4450(3) 0.9720(3) 0.1432(3) 0.0579(9) Uani 1 1 d . . .
H13A H 0.3854 0.9288 0.1926 0.069 Uiso 1 1 calc R . .
H13B H 0.5225 0.9194 0.1327 0.069 Uiso 1 1 calc R . .
C14 C 0.2731(3) 1.4250(3) 0.0450(3) 0.0676(10) Uani 1 1 d . . .
H14A H 0.3372 1.4552 0.0966 0.101 Uiso 1 1 calc R . .
H14B H 0.1988 1.4812 0.0423 0.101 Uiso 1 1 calc R . .
H14C H 0.3136 1.42 -0.0255 0.101 Uiso 1 1 calc R . .
F1 F 0.14515(19) 0.72224(15) 0.00043(18) 0.0853(7) Uani 1 1 d . . .
N1 N 0.0008(2) 0.8632(2) 0.1365(2) 0.0502(7) Uani 1 1 d . . .
N2 N 0.2183(2) 1.1144(2) -0.0753(2) 0.0441(6) Uani 1 1 d . . .
O1 O 0.5966(3) 1.1033(3) 0.2367(2) 0.1061(11) Uani 1 1 d . . .
O2 O 0.3023(2) 1.1439(2) -0.14134(18) 0.0652(6) Uani 1 1 d . . .
O3 O 0.1010(2) 1.1044(3) -0.09737(19) 0.0758(8) Uani 1 1 d . . .
O4 O 0.22907(19) 1.30632(18) 0.07662(19) 0.0616(6) 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 0 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
N1 C1 C2 124.0(3) . . ?
N1 C1 H1 118 . . ?
C2 C1 H1 118 . . ?
C1 C2 C3 118.9(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 119.4(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C9 116.9(2) . . ?
C3 C4 C5 125.3(2) . . ?
C9 C4 C5 117.8(2) . . ?
C4 C5 C6 112.0(2) . . ?
C4 C5 C10 116.7(2) . . ?
C6 C5 C10 109.48(19) . . ?
C4 C5 N2 107.15(19) . . ?
C6 C5 N2 106.0(2) . . ?
C10 C5 N2 104.7(2) . . ?
C7 C6 C5 111.0(2) . . ?
C7 C6 C13 109.6(2) . . ?
C5 C6 C13 110.2(2) . . ?
C7 C6 H6 108.7 . . ?
C5 C6 H6 108.7 . . ?
C13 C6 H6 108.7 . . ?
C8 C7 C6 119.4(3) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 F1 120.9(3) . . ?
C7 C8 C9 124.3(3) . . ?
F1 C8 C9 114.8(2) . . ?
N1 C9 C4 123.8(3) . . ?
N1 C9 C8 118.4(2) . . ?
C4 C9 C8 117.8(2) . . ?
O4 C10 C11 113.1(2) . . ?
O4 C10 C5 109.27(19) . . ?
C11 C10 C5 110.6(2) . . ?
O4 C10 H10 107.9 . . ?
C11 C10 H10 107.9 . . ?
C5 C10 H10 107.9 . . ?
C12 C11 C10 111.5(3) . . ?
C12 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108 . . ?
O1 C12 C13 122.1(4) . . ?
O1 C12 C11 122.5(4) . . ?
C13 C12 C11 115.5(2) . . ?
C12 C13 C6 114.3(3) . . ?
C12 C13 H13A 108.7 . . ?
C6 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
C6 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 N1 C9 116.9(2) . . ?
O2 N2 O3 123.3(2) . . ?
O2 N2 C5 117.6(2) . . ?
O3 N2 C5 119.2(2) . . ?
C14 O4 C10 116.5(2) . . ?
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
C1 N1 1.328(4) . ?
C1 C2 1.366(4) . ?
C1 H1 0.93 . ?
C2 C3 1.380(4) . ?
C2 H2 0.93 . ?
C3 C4 1.385(3) . ?
C3 H3 0.93 . ?
C4 C9 1.405(4) . ?
C4 C5 1.518(3) . ?
C5 C6 1.527(3) . ?
C5 C10 1.536(4) . ?
C5 N2 1.549(4) . ?
C6 C7 1.505(4) . ?
C6 C13 1.544(4) . ?
C6 H6 0.98 . ?
C7 C8 1.303(4) . ?
C7 H7 0.93 . ?
C8 F1 1.352(3) . ?
C8 C9 1.466(4) . ?
C9 N1 1.338(3) . ?
C10 O4 1.416(3) . ?
C10 C11 1.521(4) . ?
C10 H10 0.98 . ?
C11 C12 1.504(5) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 O1 1.205(4) . ?
C12 C13 1.500(5) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 O4 1.402(3) . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
N2 O2 1.214(3) . ?
N2 O3 1.214(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
N1 C1 C2 C3 2.9(5) . . . . ?
C1 C2 C3 C4 -2.1(4) . . . . ?
C2 C3 C4 C9 -0.1(4) . . . . ?
C2 C3 C4 C5 177.0(2) . . . . ?
C3 C4 C5 C6 147.2(3) . . . . ?
C9 C4 C5 C6 -35.8(3) . . . . ?
C3 C4 C5 C10 19.9(4) . . . . ?
C9 C4 C5 C10 -163.0(2) . . . . ?
C3 C4 C5 N2 -96.9(3) . . . . ?
C9 C4 C5 N2 80.1(3) . . . . ?
C4 C5 C6 C7 48.1(3) . . . . ?
C10 C5 C6 C7 179.1(2) . . . . ?
N2 C5 C6 C7 -68.5(3) . . . . ?
C4 C5 C6 C13 -73.6(3) . . . . ?
C10 C5 C6 C13 57.5(3) . . . . ?
N2 C5 C6 C13 169.9(2) . . . . ?
C5 C6 C7 C8 -32.6(4) . . . . ?
C13 C6 C7 C8 89.3(3) . . . . ?
C6 C7 C8 F1 -176.2(3) . . . . ?
C6 C7 C8 C9 1.5(5) . . . . ?
C3 C4 C9 N1 1.7(4) . . . . ?
C5 C4 C9 N1 -175.5(2) . . . . ?
C3 C4 C9 C8 -177.4(3) . . . . ?
C5 C4 C9 C8 5.3(4) . . . . ?
C7 C8 C9 N1 -165.6(3) . . . . ?
F1 C8 C9 N1 12.2(4) . . . . ?
C7 C8 C9 C4 13.6(5) . . . . ?
F1 C8 C9 C4 -168.6(2) . . . . ?
C4 C5 C10 O4 -58.7(3) . . . . ?
C6 C5 C10 O4 172.7(2) . . . . ?
N2 C5 C10 O4 59.5(3) . . . . ?
C4 C5 C10 C11 66.4(3) . . . . ?
C6 C5 C10 C11 -62.1(3) . . . . ?
N2 C5 C10 C11 -175.4(2) . . . . ?
O4 C10 C11 C12 178.8(2) . . . . ?
C5 C10 C11 C12 55.8(3) . . . . ?
C10 C11 C12 O1 133.4(3) . . . . ?
C10 C11 C12 C13 -47.3(4) . . . . ?
O1 C12 C13 C6 -136.2(3) . . . . ?
C11 C12 C13 C6 44.5(4) . . . . ?
C7 C6 C13 C12 -171.5(3) . . . . ?
C5 C6 C13 C12 -49.1(3) . . . . ?
C2 C1 N1 C9 -1.3(5) . . . . ?
C4 C9 N1 C1 -1.1(4) . . . . ?
C8 C9 N1 C1 178.1(3) . . . . ?
C4 C5 N2 O2 -174.3(2) . . . . ?
C6 C5 N2 O2 -54.5(3) . . . . ?
C10 C5 N2 O2 61.2(3) . . . . ?
C4 C5 N2 O3 5.3(3) . . . . ?
C6 C5 N2 O3 125.0(3) . . . . ?
C10 C5 N2 O3 -119.2(3) . . . . ?
C11 C10 O4 C14 93.3(3) . . . . ?
C5 C10 O4 C14 -143.0(3) . . . . ?
