#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:40:18 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281566 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/90/7159054.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_7159054
loop_
_publ_author_name
'Lv, Yanxia'
'Hou, Zhong-Wei'
'Wang, Yi'
'Li, Pinhua'
'Wang, Lei'
_publ_section_title
;
 Electrochemical monofluoroalkylation cyclization of
 N-arylacrylamides to construct monofluorinated 2-oxindoles.
;
_journal_issue                   5
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1014
_journal_page_last               1020
_journal_paper_doi               10.1039/d2ob01883g
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C17 H20 F N O5'
_chemical_formula_weight         337.34
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2022-06-07 deposited with the CCDC.	2022-12-26 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.264(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.456(6)
_cell_length_b                   8.301(3)
_cell_length_c                   13.506(5)
_cell_measurement_reflns_used    1706
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.90
_cell_measurement_theta_min      2.80
_cell_volume                     1693.3(11)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8058
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.80
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_correction_T_min  0.9734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2963
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0474
_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)+(0.0500P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1245
_reflns_number_gt                1928
_reflns_number_total             2963
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2ob01883g2.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7159054.cif.
;
_cod_original_cell_volume        1693.3(12)
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               7159054
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
N1 N 0.29040(13) 0.6777(2) 0.43452(14) 0.0615(5) Uani 1 1 d . . .
F1 F 0.22996(9) 0.32941(16) 0.35361(10) 0.0764(4) Uani 1 1 d . . .
O1 O 0.14960(12) 0.6752(2) 0.33672(14) 0.0830(6) Uani 1 1 d . . .
O2 O 0.32286(11) 0.1259(2) 0.48014(15) 0.0878(6) Uani 1 1 d . . .
O3 O 0.21763(10) 0.10723(18) 0.57050(11) 0.0611(4) Uani 1 1 d . . .
O4 O 0.11178(12) 0.1264(2) 0.26169(13) 0.0835(6) Uani 1 1 d . . .
O5 O 0.06336(10) 0.07438(19) 0.40305(11) 0.0670(5) Uani 1 1 d . . .
C1 C 0.44600(19) 0.5432(5) 0.6690(3) 0.0987(11) Uani 1 1 d . . .
H1A H 0.5044 0.5491 0.7047 0.118 Uiso 1 1 calc R . .
C2 C 0.3872(2) 0.4547(4) 0.7100(2) 0.0900(9) Uani 1 1 d . . .
H2A H 0.4065 0.4011 0.7711 0.108 Uiso 1 1 calc R . .
C3 C 0.29924(17) 0.4453(3) 0.66053(17) 0.0637(6) Uani 1 1 d . . .
H3A H 0.2584 0.3887 0.6886 0.076 Uiso 1 1 calc R . .
C4 C 0.27382(14) 0.5219(2) 0.56853(15) 0.0485(5) Uani 1 1 d . . .
C5 C 0.33467(14) 0.6101(3) 0.52716(17) 0.0549(6) Uani 1 1 d . . .
C6 C 0.42298(16) 0.6244(4) 0.5771(2) 0.0780(8) Uani 1 1 d . . .
C7 C 0.49245(18) 0.7229(5) 0.5411(3) 0.1248(15) Uani 1 1 d . . .
H7A H 0.4669 0.7716 0.4771 0.187 Uiso 1 1 calc R . .
H7B H 0.5406 0.6543 0.5335 0.187 Uiso 1 1 calc R . .
H7C H 0.5140 0.8055 0.5899 0.187 Uiso 1 1 calc R . .
C8 C 0.3282(2) 0.7699(3) 0.3618(2) 0.0957(10) Uani 1 1 d . . .
H8A H 0.2820 0.8003 0.3055 0.144 Uiso 1 1 calc R . .
H8B H 0.3710 0.7050 0.3381 0.144 Uiso 1 1 calc R . .
H8C H 0.3564 0.8649 0.3941 0.144 Uiso 1 1 calc R . .
C9 C 0.20322(16) 0.6365(3) 0.41279(18) 0.0577(6) Uani 1 1 d . . .
C10 C 0.12282(15) 0.6436(3) 0.5536(2) 0.0692(7) Uani 1 1 d . . .
H10A H 0.1530 0.7417 0.5777 0.104 Uiso 1 1 calc R . .
H10B H 0.1088 0.5855 0.6096 0.104 Uiso 1 1 calc R . .
H10C H 0.0692 0.6685 0.5056 0.104 Uiso 1 1 calc R . .
C11 C 0.18304(13) 0.5394(2) 0.50201(15) 0.0482(5) Uani 1 1 d . . .
C12 C 0.13272(13) 0.3838(2) 0.46465(17) 0.0511(5) Uani 1 1 d . . .
H12A H 0.1133 0.3353 0.5215 0.061 Uiso 1 1 calc R . .
H12B H 0.0800 0.4130 0.4149 0.061 Uiso 1 1 calc R . .
C13 C 0.18260(14) 0.2558(3) 0.41756(16) 0.0524(5) Uani 1 1 d . . .
C14 C 0.25077(14) 0.1570(3) 0.49342(18) 0.0557(6) Uani 1 1 d . . .
C15 C 0.27651(18) 0.0137(3) 0.64727(19) 0.0826(8) Uani 1 1 d . . .
H15A H 0.2461 -0.0165 0.6994 0.124 Uiso 1 1 calc R . .
H15B H 0.3275 0.0773 0.6762 0.124 Uiso 1 1 calc R . .
H15C H 0.2949 -0.0814 0.6170 0.124 Uiso 1 1 calc R . .
C16 C 0.11623(14) 0.1425(3) 0.35007(17) 0.0537(6) Uani 1 1 d . . .
C17 C -0.00505(15) -0.0318(3) 0.34786(18) 0.0712(7) Uani 1 1 d . . .
H17A H -0.0391 -0.0748 0.3935 0.107 Uiso 1 1 calc R . .
H17B H 0.0220 -0.1186 0.3185 0.107 Uiso 1 1 calc R . .
H17C H -0.0433 0.0278 0.2952 0.107 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 N1 C5 111.32(18) . . ?
C9 N1 C8 120.4(2) . . ?
C5 N1 C8 128.1(2) . . ?
C14 O3 C15 116.20(19) . . ?
C16 O5 C17 116.58(17) . . ?
C2 C1 C6 123.6(3) . . ?
C2 C1 H1A 118.2 . . ?
C6 C1 H1A 118.2 . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 H2A 119.9 . . ?
C4 C3 C2 118.2(3) . . ?
C4 C3 H3A 120.9 . . ?
C2 C3 H3A 120.9 . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 C11 129.4(2) . . ?
C5 C4 C11 109.39(18) . . ?
C6 C5 C4 121.6(2) . . ?
C6 C5 N1 129.6(2) . . ?
C4 C5 N1 108.80(19) . . ?
C1 C6 C5 115.4(3) . . ?
C1 C6 C7 119.0(3) . . ?
C5 C6 C7 125.5(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 N1 125.5(2) . . ?
O1 C9 C11 125.8(2) . . ?
N1 C9 C11 108.64(19) . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C11 C9 101.55(17) . . ?
C4 C11 C12 117.24(17) . . ?
C9 C11 C12 110.90(17) . . ?
C4 C11 C10 111.14(17) . . ?
C9 C11 C10 107.62(18) . . ?
C12 C11 C10 107.95(17) . . ?
C13 C12 C11 117.14(16) . . ?
C13 C12 H12A 108.0 . . ?
C11 C12 H12A 108.0 . . ?
C13 C12 H12B 108.0 . . ?
C11 C12 H12B 108.0 . . ?
H12A C12 H12B 107.3 . . ?
F1 C13 C12 109.43(17) . . ?
F1 C13 C16 105.89(17) . . ?
C12 C13 C16 109.84(17) . . ?
F1 C13 C14 105.77(17) . . ?
C12 C13 C14 115.31(18) . . ?
C16 C13 C14 110.13(17) . . ?
O2 C14 O3 125.5(2) . . ?
O2 C14 C13 122.9(2) . . ?
O3 C14 C13 111.46(18) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 O5 125.8(2) . . ?
O4 C16 C13 123.5(2) . . ?
O5 C16 C13 110.58(18) . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O5 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
N1 C9 1.360(3) . ?
N1 C5 1.409(3) . ?
N1 C8 1.461(3) . ?
F1 C13 1.387(2) . ?
O1 C9 1.218(3) . ?
O2 C14 1.194(3) . ?
O3 C14 1.320(3) . ?
O3 C15 1.451(3) . ?
O4 C16 1.188(3) . ?
O5 C16 1.322(2) . ?
O5 C17 1.455(2) . ?
C1 C2 1.373(4) . ?
C1 C6 1.391(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.383(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.377(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.399(3) . ?
C4 C11 1.504(3) . ?
C5 C6 1.393(3) . ?
C6 C7 1.510(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C11 1.536(3) . ?
C10 C11 1.541(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.537(3) . ?
C12 C13 1.528(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C16 1.540(3) . ?
C13 C14 1.541(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
