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#$Date: 2022-02-15 00:54:00 +0200 (Tue, 15 Feb 2022) $
#$Revision: 272949 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/97/7129709.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_7129709
loop_
_publ_author_name
'Wang, Fei'
'Fu , Rui'
'Chen, Jie'
'Rong, Jiaxin'
'Wang, Enfu'
'Zhang, Jian'
'Zhang, Zhengyu'
'Jiang, Yaojia'
_publ_section_title
;
 Metal-Free Synthesis of gem-Difluorinated Heterocycles from Enaminones
 and Difluorocarbene Precursors
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00383J
_journal_year                    2022
_chemical_formula_sum            'C12 H12 F2 N2 O3'
_chemical_formula_weight         270.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-06-03 deposited with the CCDC.	2022-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                112.726(5)
_cell_angle_beta                 100.067(5)
_cell_angle_gamma                90.297(6)
_cell_formula_units_Z            2
_cell_length_a                   7.6940(11)
_cell_length_b                   9.3007(14)
_cell_length_c                   9.6264(13)
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    304(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      3.74
_cell_volume                     623.59(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      304(2)
_diffrn_measured_fraction_theta_full 0.883
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.883
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18902
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.629
_diffrn_reflns_theta_min         3.740
_exptl_absorpt_coefficient_mu    0.124
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.519
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.159
_refine_ls_R_factor_all          0.1892
_refine_ls_R_factor_gt           0.1660
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4397
_refine_ls_wR_factor_ref         0.4786
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1877
_reflns_number_total             2503
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc00383j2.cif
_cod_data_source_block           a
_cod_database_code               7129709
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.0861(5) 0.7244(4) -0.1806(5) 0.0503(11) Uani 1 1 d . . . . .
N2 N 0.8331(5) 1.0789(5) 0.5910(5) 0.0544(12) Uani 1 1 d . . . . .
O1 O 0.1974(6) 0.8752(5) -0.0276(6) 0.0783(14) Uani 1 1 d . . . . .
O2 O 0.8488(7) 1.2204(5) 0.6580(6) 0.0896(16) Uani 1 1 d . . . . .
O3 O 0.9140(5) 0.9916(5) 0.6380(5) 0.0663(12) Uani 1 1 d . . . . .
C1 C 0.0997(6) 0.7569(5) -0.1744(5) 0.0479(12) Uani 1 1 d . . . . .
H1 H 0.1093 0.7935 -0.2558 0.058 Uiso 1 1 calc R U . . .
C2 C 0.2215(6) 0.6206(5) -0.1911(5) 0.0481(12) Uani 1 1 d . . . . .
C3 C 0.3448(5) 0.6619(4) -0.0584(4) 0.0373(10) Uani 1 1 d . . . . .
H3 H 0.4238 0.5970 -0.0323 0.045 Uiso 1 1 calc R U . . .
C4 C 0.3309(6) 0.8196(4) 0.0313(5) 0.0419(11) Uani 1 1 d . . . . .
C5 C 0.4635(5) 0.8850(5) 0.1723(5) 0.0402(11) Uani 1 1 d . . . . .
C6 C 0.4770(7) 1.0451(5) 0.2590(6) 0.0494(12) Uani 1 1 d . . . . .
H6 H 0.4031 1.1089 0.2257 0.059 Uiso 1 1 calc R U . . .
C7 C 0.5992(6) 1.1098(5) 0.3942(6) 0.0484(12) Uani 1 1 d . . . . .
H7 H 0.6106 1.2172 0.4515 0.058 Uiso 1 1 calc R U . . .
C8 C 0.7048(5) 1.0114(5) 0.4430(5) 0.0441(11) Uani 1 1 d . . . . .
C9 C 0.6961(6) 0.8545(6) 0.3596(6) 0.0494(12) Uani 1 1 d . . . . .
H9 H 0.7706 0.7917 0.3938 0.059 Uiso 1 1 calc R U . . .
C10 C 0.5735(6) 0.7893(5) 0.2217(5) 0.0477(12) Uani 1 1 d . . . . .
H10 H 0.5656 0.6823 0.1634 0.057 Uiso 1 1 calc R U . . .
C11 C -0.1810(8) 0.6234(6) -0.3314(7) 0.0668(15) Uani 1 1 d . . . . .
H11A H -0.1436 0.6531 -0.4073 0.100 Uiso 1 1 calc R U . . .
H11B H -0.3059 0.6332 -0.3362 0.100 Uiso 1 1 calc R U . . .
H11C H -0.1567 0.5169 -0.3509 0.100 Uiso 1 1 calc R U . . .
C12 C -0.1244(9) 0.6792(8) -0.0589(8) 0.0739(17) Uani 1 1 d . . . . .
H12A H -0.2365 0.7146 -0.0345 0.111 Uiso 1 1 calc R U . . .
H12B H -0.0331 0.7259 0.0307 0.111 Uiso 1 1 calc R U . . .
H12C H -0.1287 0.5674 -0.0930 0.111 Uiso 1 1 calc R U . . .
F1 F 0.1429(4) 0.4829(3) -0.2193(4) 0.0709(11) Uani 1 1 d . . . . .
F2 F 0.3130(5) 0.5947(4) -0.3060(4) 0.0804(12) 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
C1 N1 C11 113.8(4) . . ?
C1 N1 C12 114.9(4) . . ?
C11 N1 C12 113.1(5) . . ?
O3 N2 O2 123.8(4) . . ?
O3 N2 C8 118.6(4) . . ?
O2 N2 C8 117.5(4) . . ?
C4 O1 C1 111.9(4) . . ?
N1 C1 O1 115.8(4) . . ?
N1 C1 C2 117.4(4) . . ?
O1 C1 C2 99.2(4) . . ?
F1 C2 F2 105.2(4) . . ?
F1 C2 C3 107.8(4) . . ?
F2 C2 C3 106.5(4) . . ?
F1 C2 C1 116.5(4) . . ?
F2 C2 C1 112.0(4) . . ?
C3 C2 C1 108.3(3) . . ?
C2 C3 C4 107.8(3) . . ?
O1 C4 C3 112.0(4) . . ?
O1 C4 C5 133.4(4) . . ?
C3 C4 C5 114.5(4) . . ?
C10 C5 C6 120.0(4) . . ?
C10 C5 C4 120.9(4) . . ?
C6 C5 C4 119.1(4) . . ?
C7 C6 C5 120.4(4) . . ?
C6 C7 C8 118.6(4) . . ?
C9 C8 C7 122.3(4) . . ?
C9 C8 N2 118.5(4) . . ?
C7 C8 N2 119.2(4) . . ?
C8 C9 C10 119.0(4) . . ?
C5 C10 C9 119.7(4) . . ?
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
N1 C1 1.446(6) . ?
N1 C11 1.446(7) . ?
N1 C12 1.461(7) . ?
N2 O3 1.200(6) . ?
N2 O2 1.215(6) . ?
N2 C8 1.486(6) . ?
O1 C4 1.293(6) . ?
O1 C1 1.480(7) . ?
C1 C2 1.555(6) . ?
C2 F1 1.321(6) . ?
C2 F2 1.358(6) . ?
C2 C3 1.369(6) . ?
C3 C4 1.401(5) . ?
C4 C5 1.457(6) . ?
C5 C10 1.389(6) . ?
C5 C6 1.391(6) . ?
C6 C7 1.379(7) . ?
C7 C8 1.388(7) . ?
C8 C9 1.361(7) . ?
C9 C10 1.397(7) . ?
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
C11 N1 C1 O1 172.6(4) . . . . ?
C12 N1 C1 O1 -54.6(5) . . . . ?
C11 N1 C1 C2 -70.7(5) . . . . ?
C12 N1 C1 C2 62.1(6) . . . . ?
C4 O1 C1 N1 122.4(5) . . . . ?
C4 O1 C1 C2 -4.1(5) . . . . ?
N1 C1 C2 F1 4.1(6) . . . . ?
O1 C1 C2 F1 129.6(4) . . . . ?
N1 C1 C2 F2 125.2(4) . . . . ?
O1 C1 C2 F2 -109.3(4) . . . . ?
N1 C1 C2 C3 -117.6(5) . . . . ?
O1 C1 C2 C3 7.9(5) . . . . ?
F1 C2 C3 C4 -135.8(4) . . . . ?
F2 C2 C3 C4 111.7(4) . . . . ?
C1 C2 C3 C4 -9.0(5) . . . . ?
C1 O1 C4 C3 -1.1(6) . . . . ?
C1 O1 C4 C5 -178.4(4) . . . . ?
C2 C3 C4 O1 6.6(6) . . . . ?
C2 C3 C4 C5 -175.5(4) . . . . ?
O1 C4 C5 C10 167.6(5) . . . . ?
C3 C4 C5 C10 -9.8(6) . . . . ?
O1 C4 C5 C6 -11.4(8) . . . . ?
C3 C4 C5 C6 171.3(4) . . . . ?
C10 C5 C6 C7 0.0(7) . . . . ?
C4 C5 C6 C7 178.9(4) . . . . ?
C5 C6 C7 C8 -1.5(7) . . . . ?
C6 C7 C8 C9 2.3(7) . . . . ?
C6 C7 C8 N2 -178.1(4) . . . . ?
O3 N2 C8 C9 -6.0(6) . . . . ?
O2 N2 C8 C9 174.4(4) . . . . ?
O3 N2 C8 C7 174.3(4) . . . . ?
O2 N2 C8 C7 -5.2(6) . . . . ?
C7 C8 C9 C10 -1.6(7) . . . . ?
N2 C8 C9 C10 178.7(4) . . . . ?
C6 C5 C10 C9 0.7(7) . . . . ?
C4 C5 C10 C9 -178.2(4) . . . . ?
C8 C9 C10 C5 0.1(7) . . . . ?
