#------------------------------------------------------------------------------
#$Date: 2022-09-27 00:53:41 +0300 (Tue, 27 Sep 2022) $
#$Revision: 278195 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/07/7130770.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_7130770
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_compound_source        'synthesis as described'
_chemical_formula_moiety         'C15 H14 F1 N1 O4'
_chemical_formula_sum            'C15 H14 F N O4'
_chemical_formula_weight         291.27
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_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             2020-12-02T15:07:13-00:00
_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                 104.883(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5797(18)
_cell_length_b                   8.1298(12)
_cell_length_c                   13.6651(19)
_cell_measurement_reflns_used    1542
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.24
_cell_measurement_theta_min      2.94
_cell_measurement_wavelength     0.71073
_cell_volume                     1350.7(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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0384
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5814
_diffrn_reflns_theta_full        23.24
_diffrn_reflns_theta_max         23.24
_diffrn_reflns_theta_min         2.94
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.432
_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         0.29
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.04
_refine_ls_extinction_coef       0.018(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   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         1923
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0447
_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)+(0.0811P)²+0.0660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1334
_reflns_number_gt                1542
_reflns_number_total             1923
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            d2cc04778k2.cif
_cod_data_source_block           br924
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               7130770
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
C1 C 0.43975(16) 0.1887(2) 0.24310(14) 0.0437(5) Uani 1 1 d . . .
C2 C 0.36677(16) 0.0914(2) 0.29566(15) 0.0458(5) Uani 1 1 d . . .
C3 C 0.29360(19) -0.0267(3) 0.24640(18) 0.0612(7) Uani 1 1 d . . .
H3 H 0.2842 -0.0441 0.1774 0.073 Uiso 1 1 calc R . .
C4 C 0.2339(2) -0.1196(3) 0.2988(3) 0.0781(8) Uani 1 1 d . . .
H4 H 0.1843 -0.1983 0.2649 0.094 Uiso 1 1 calc R . .
C5 C 0.2480(2) -0.0954(3) 0.4005(3) 0.0771(8) Uani 1 1 d . . .
H5 H 0.208 -0.1585 0.4353 0.093 Uiso 1 1 calc R . .
C6 C 0.3206(2) 0.0213(3) 0.45180(19) 0.0623(7) Uani 1 1 d . . .
H6 H 0.3291 0.0374 0.5208 0.075 Uiso 1 1 calc R . .
C7 C 0.38118(17) 0.1147(2) 0.40030(15) 0.0467(5) Uani 1 1 d . . .
C8 C 0.46123(17) 0.2364(2) 0.45136(15) 0.0462(6) Uani 1 1 d . . .
C9 C 0.50813(17) 0.3446(3) 0.40622(15) 0.0498(6) Uani 1 1 d . . .
H9 H 0.5619 0.4145 0.4438 0.06 Uiso 1 1 calc R . .
C10 C 0.47463(16) 0.3556(2) 0.29280(14) 0.0445(5) Uani 1 1 d . . .
H10 H 0.5377 0.3954 0.2699 0.053 Uiso 1 1 calc R . .
C11 C 0.38068(18) 0.4829(2) 0.26127(15) 0.0525(6) Uani 1 1 d . . .
H11A H 0.3268 0.4611 0.2993 0.063 Uiso 1 1 calc R . .
H11B H 0.4107 0.5916 0.2803 0.063 Uiso 1 1 calc R . .
C12 C 0.32318(18) 0.4842(3) 0.15089(16) 0.0543(6) Uani 1 1 d . . .
C13 C 0.29384(18) 0.3192(3) 0.10443(16) 0.0575(6) Uani 1 1 d . . .
H13A H 0.2662 0.3305 0.0316 0.069 Uiso 1 1 calc R . .
H13B H 0.2363 0.2707 0.1306 0.069 Uiso 1 1 calc R . .
C14 C 0.39464(18) 0.2074(3) 0.12848(15) 0.0509(6) Uani 1 1 d . . .
H14 H 0.3753 0.0992 0.0973 0.061 Uiso 1 1 calc R . .
C15 C 0.4694(3) 0.2603(4) -0.01158(18) 0.0905(10) Uani 1 1 d . . .
H15A H 0.4479 0.1496 -0.0319 0.136 Uiso 1 1 calc R . .
H15B H 0.538 0.2848 -0.027 0.136 Uiso 1 1 calc R . .
H15C H 0.4139 0.3352 -0.0474 0.136 Uiso 1 1 calc R . .
F1 F 0.48418(12) 0.23129(16) 0.55469(9) 0.0698(5) Uani 1 1 d . . .
N1 N 0.54581(17) 0.0811(2) 0.25476(14) 0.0583(5) Uani 1 1 d . . .
O1 O 0.29846(16) 0.6104(2) 0.10323(13) 0.0848(6) Uani 1 1 d . . .
O2 O 0.48177(13) 0.27693(19) 0.09401(11) 0.0634(5) Uani 1 1 d . . .
O3 O 0.53208(16) -0.0575(2) 0.21989(13) 0.0868(6) Uani 1 1 d . . .
O4 O 0.63472(14) 0.1381(2) 0.29799(14) 0.0825(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
C2 C1 C14 115.08(17) . . ?
C2 C1 C10 112.93(15) . . ?
C14 C1 C10 110.78(16) . . ?
C2 C1 N1 105.22(15) . . ?
C14 C1 N1 103.98(15) . . ?
C10 C1 N1 108.05(16) . . ?
C3 C2 C7 119.00(19) . . ?
C3 C2 C1 122.56(18) . . ?
C7 C2 C1 118.25(17) . . ?
C2 C3 C4 120.6(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120 . . ?
C3 C4 H4 120 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C7 119.8(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C2 119.8(2) . . ?
C6 C7 C8 122.1(2) . . ?
C2 C7 C8 118.10(18) . . ?
C9 C8 F1 120.61(19) . . ?
C9 C8 C7 125.11(19) . . ?
F1 C8 C7 114.27(18) . . ?
C8 C9 C10 119.28(19) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C1 112.20(16) . . ?
C9 C10 C11 108.62(16) . . ?
C1 C10 C11 110.99(16) . . ?
C9 C10 H10 108.3 . . ?
C1 C10 H10 108.3 . . ?
C11 C10 H10 108.3 . . ?
C12 C11 C10 115.01(17) . . ?
C12 C11 H11A 108.5 . . ?
C10 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C10 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?
O1 C12 C13 122.1(2) . . ?
O1 C12 C11 122.6(2) . . ?
C13 C12 C11 115.20(18) . . ?
C12 C13 C14 110.10(18) . . ?
C12 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.2 . . ?
O2 C14 C13 111.19(17) . . ?
O2 C14 C1 105.35(16) . . ?
C13 C14 C1 110.42(17) . . ?
O2 C14 H14 109.9 . . ?
C13 C14 H14 109.9 . . ?
C1 C14 H14 109.9 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 N1 O3 124.3(2) . . ?
O4 N1 C1 119.31(18) . . ?
O3 N1 C1 116.39(19) . . ?
C15 O2 C14 114.10(18) . . ?
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 C2 1.524(3) . ?
C1 C14 1.530(3) . ?
C1 C10 1.531(3) . ?
C1 N1 1.569(3) . ?
C2 C3 1.380(3) . ?
C2 C7 1.407(3) . ?
C3 C4 1.387(4) . ?
C3 H3 0.93 . ?
C4 C5 1.369(4) . ?
C4 H4 0.93 . ?
C5 C6 1.378(4) . ?
C5 H5 0.93 . ?
C6 C7 1.388(3) . ?
C6 H6 0.93 . ?
C7 C8 1.456(3) . ?
C8 C9 1.300(3) . ?
C8 F1 1.367(2) . ?
C9 C10 1.501(3) . ?
C9 H9 0.93 . ?
C10 C11 1.546(3) . ?
C10 H10 0.98 . ?
C11 C12 1.496(3) . ?
C11 H11A 0.97 . ?
C11 H11B 0.97 . ?
C12 O1 1.212(2) . ?
C12 C13 1.490(3) . ?
C13 C14 1.526(3) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 O2 1.417(3) . ?
C14 H14 0.98 . ?
C15 O2 1.417(3) . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?
N1 O4 1.215(2) . ?
N1 O3 1.218(2) . ?
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 26.4(3) . . . . ?
C10 C1 C2 C3 154.92(19) . . . . ?
N1 C1 C2 C3 -87.4(2) . . . . ?
C14 C1 C2 C7 -158.68(17) . . . . ?
C10 C1 C2 C7 -30.1(2) . . . . ?
N1 C1 C2 C7 87.5(2) . . . . ?
C7 C2 C3 C4 0.9(3) . . . . ?
C1 C2 C3 C4 175.8(2) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C5 C6 C7 C2 1.0(3) . . . . ?
C5 C6 C7 C8 -178.28(19) . . . . ?
C3 C2 C7 C6 -1.1(3) . . . . ?
C1 C2 C7 C6 -176.29(17) . . . . ?
C3 C2 C7 C8 178.16(18) . . . . ?
C1 C2 C7 C8 3.0(3) . . . . ?
C6 C7 C8 C9 -168.9(2) . . . . ?
C2 C7 C8 C9 11.8(3) . . . . ?
C6 C7 C8 F1 10.2(3) . . . . ?
C2 C7 C8 F1 -169.12(16) . . . . ?
F1 C8 C9 C10 -175.25(16) . . . . ?
C7 C8 C9 C10 3.8(3) . . . . ?
C8 C9 C10 C1 -31.6(3) . . . . ?
C8 C9 C10 C11 91.5(2) . . . . ?
C2 C1 C10 C9 43.2(2) . . . . ?
C14 C1 C10 C9 173.96(16) . . . . ?
N1 C1 C10 C9 -72.75(19) . . . . ?
C2 C1 C10 C11 -78.5(2) . . . . ?
C14 C1 C10 C11 52.2(2) . . . . ?
N1 C1 C10 C11 165.52(15) . . . . ?
C9 C10 C11 C12 -168.48(18) . . . . ?
C1 C10 C11 C12 -44.7(2) . . . . ?
C10 C11 C12 O1 -137.2(2) . . . . ?
C10 C11 C12 C13 45.4(3) . . . . ?
O1 C12 C13 C14 131.0(2) . . . . ?
C11 C12 C13 C14 -51.6(3) . . . . ?
C12 C13 C14 O2 -57.5(2) . . . . ?
C12 C13 C14 C1 59.0(2) . . . . ?
C2 C1 C14 O2 -170.92(15) . . . . ?
C10 C1 C14 O2 59.5(2) . . . . ?
N1 C1 C14 O2 -56.40(19) . . . . ?
C2 C1 C14 C13 68.9(2) . . . . ?
C10 C1 C14 C13 -60.7(2) . . . . ?
N1 C1 C14 C13 -176.54(17) . . . . ?
C2 C1 N1 O4 -120.8(2) . . . . ?
C14 C1 N1 O4 117.8(2) . . . . ?
C10 C1 N1 O4 0.1(2) . . . . ?
C2 C1 N1 O3 58.3(2) . . . . ?
C14 C1 N1 O3 -63.1(2) . . . . ?
C10 C1 N1 O3 179.19(17) . . . . ?
C13 C14 O2 C15 -78.0(2) . . . . ?
C1 C14 O2 C15 162.42(19) . . . . ?
