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#$Date: 2024-08-07 23:53:23 +0200 (Wed 07 de Aug de 2024) $
#$Revision: 294035 $
#$URL: svn://www.crystallography.net/cod/cif/7/13/34/7133466.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_7133466
loop_
_publ_author_name
'Giannessi, Lisa'
'Longo, Matteo'
'Massera, Chiara'
'Radi, Marco'
_publ_section_title
;
 Late-Stage Functionalization of the 4-amino-2-Pyridone Chemotype Using
 Electrochemical and MCR approaches
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D4CC02473G
_journal_year                    2024
_chemical_formula_moiety         '(C23 H17 F6 N3 O1 S1), 0.5 (H2O)'
_chemical_formula_sum            'C23 H18 F6 N3 O1.5 S'
_chemical_formula_weight         506.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-04-25 deposited with the CCDC.	2024-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   13.8237(7)
_cell_length_b                   50.8400(10)
_cell_length_c                   12.4078(5)
_cell_measurement_reflns_used    2684
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      74.778
_cell_measurement_theta_min      3.477
_cell_volume                     8720.2(6)
_computing_cell_refinement       'SAINT V8.38A (2016)'
_computing_data_collection       'Apex III (2016)'
_computing_data_reduction        'SAINT V8.38A (2016)'
_computing_molecular_graphics
;
 Mercury CSD 2023.3.1 (Macrae et al., 2006)
;
_computing_publication_material
'SHELXL and WINGX (Farrugia, J. App. Cryst.2012, 45, 849-854'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture PhotonII'
_diffrn_measurement_method       'phi & omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       63
_diffrn_reflns_limit_k_min       -62
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            35778
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.778
_diffrn_reflns_theta_min         3.477
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.021
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             4144
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform/hexane'
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4157
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0538P)²+2.2826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.0995
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.882
_reflns_Friedel_fraction_max     0.849
_reflns_number_gt                3509
_reflns_number_total             4157
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc02473g2.cif
_cod_data_source_block           7
_cod_original_formula_sum        'C23 H18 F6 N3 O1.50 S'
_cod_database_code               7133466
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_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_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
S1 S 0.69003(7) 0.48835(2) 0.652025 0.0601(2) Uani 1 1 d . . . . .
F1 F 0.4759(2) 0.34140(5) 0.9877(3) 0.0902(9) Uani 1 1 d . . . . .
F2 F 0.4332(3) 0.33054(5) 0.8290(3) 0.1008(11) Uani 1 1 d . . . . .
F3 F 0.5824(2) 0.33581(5) 0.8662(3) 0.0825(8) Uani 1 1 d . . . . .
F4 F 0.7978(2) 0.36553(5) 0.1069(3) 0.0841(8) Uani 1 1 d . . . . .
F5 F 0.7111(2) 0.37362(7) -0.0296(3) 0.1051(11) Uani 1 1 d . . . . .
F6 F 0.8501(2) 0.39158(6) -0.0147(3) 0.0962(10) Uani 1 1 d . . . . .
N1 N 0.5715(2) 0.47094(5) 0.3651(3) 0.0528(7) Uani 1 1 d . . . . .
N2 N 0.5263(2) 0.46553(5) 0.6919(3) 0.0507(7) Uani 1 1 d . . . . .
N3 N 0.6084(4) 0.47715(9) 0.8483(4) 0.0862(13) Uani 1 1 d D . . . .
O1 O 0.7175(2) 0.49065(6) 0.4025(3) 0.0790(9) Uani 1 1 d . . . . .
C1 C 0.6415(3) 0.48076(6) 0.4366(3) 0.0540(8) Uani 1 1 d . . . . .
C2 C 0.6176(3) 0.47804(6) 0.5467(3) 0.0502(8) Uani 1 1 d . . . . .
C3 C 0.5335(2) 0.46643(6) 0.5816(3) 0.0449(7) Uani 1 1 d . . . . .
C4 C 0.4665(3) 0.45669(6) 0.5058(3) 0.0481(7) Uani 1 1 d . . . . .
H4 H 0.408008 0.448662 0.528703 0.058 Uiso 1 1 calc R U . . .
C5 C 0.4874(2) 0.45902(6) 0.3995(3) 0.0500(7) Uani 1 1 d . . . . .
C6 C 0.4193(3) 0.44862(8) 0.3156(4) 0.0649(10) Uani 1 1 d . . . . .
H6A H 0.365320 0.439548 0.350910 0.097 Uiso 1 1 calc R U . . .
H6B H 0.453686 0.436257 0.268685 0.097 Uiso 1 1 calc R U . . .
H6C H 0.394242 0.463252 0.272400 0.097 Uiso 1 1 calc R U . . .
C7 C 0.6054(3) 0.47635(7) 0.7464(3) 0.0587(9) Uani 1 1 d . . . . .
C8 C 0.4460(3) 0.45405(6) 0.7518(3) 0.0546(8) Uani 1 1 d . . . . .
H8A H 0.387356 0.454386 0.706050 0.066 Uiso 1 1 calc R U . . .
H8B H 0.433020 0.465021 0.816146 0.066 Uiso 1 1 calc R U . . .
C9 C 0.4647(3) 0.42586(6) 0.7879(3) 0.0494(8) Uani 1 1 d . . . . .
C10 C 0.4599(3) 0.41921(7) 0.8948(4) 0.0589(9) Uani 1 1 d . . . . .
H10 H 0.448892 0.432513 0.947194 0.071 Uiso 1 1 calc R U . . .
C11 C 0.4710(3) 0.39319(7) 0.9277(4) 0.0625(9) Uani 1 1 d . . . . .
H11 H 0.468523 0.388862 1.002093 0.075 Uiso 1 1 calc R U . . .
C12 C 0.4855(3) 0.37388(7) 0.8526(3) 0.0531(8) Uani 1 1 d . . . . .
C13 C 0.4920(3) 0.38041(7) 0.7454(4) 0.0576(8) Uani 1 1 d . . . . .
H13 H 0.503577 0.367055 0.693456 0.069 Uiso 1 1 calc R U . . .
C14 C 0.4819(3) 0.40634(7) 0.7124(3) 0.0574(9) Uani 1 1 d . . . . .
H14 H 0.486683 0.410699 0.638152 0.069 Uiso 1 1 calc R U . . .
C15 C 0.4944(3) 0.34551(7) 0.8844(4) 0.0637(10) Uani 1 1 d . . . . .
C16 C 0.5936(4) 0.47389(7) 0.2499(4) 0.0631(10) Uani 1 1 d . . . . .
H16A H 0.636573 0.489290 0.240485 0.076 Uiso 1 1 calc R U . . .
H16B H 0.532727 0.477548 0.210670 0.076 Uiso 1 1 calc R U . . .
C17 C 0.6416(3) 0.45007(7) 0.1999(3) 0.0522(8) Uani 1 1 d . . . . .
C18 C 0.6879(3) 0.43092(7) 0.2589(3) 0.0548(8) Uani 1 1 d . . . . .
H18 H 0.691195 0.432385 0.335191 0.066 Uiso 1 1 calc R U . . .
C19 C 0.7297(3) 0.40953(7) 0.2079(3) 0.0552(9) Uani 1 1 d . . . . .
H19 H 0.760404 0.396160 0.249030 0.066 Uiso 1 1 calc R U . . .
C20 C 0.7267(3) 0.40771(7) 0.0974(3) 0.0547(8) Uani 1 1 d . . . . .
C21 C 0.6828(3) 0.42717(9) 0.0379(4) 0.0687(11) Uani 1 1 d . . . . .
H21 H 0.681784 0.425992 -0.038535 0.082 Uiso 1 1 calc R U . . .
C22 C 0.6407(4) 0.44822(9) 0.0881(4) 0.0684(11) Uani 1 1 d . . . . .
H22 H 0.610756 0.461618 0.046438 0.082 Uiso 1 1 calc R U . . .
C23 C 0.7707(3) 0.38462(9) 0.0407(4) 0.0659(10) Uani 1 1 d . . . . .
H3N H 0.6628(19) 0.4839(10) 0.864(4) 0.079(15) Uiso 1 1 d D . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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 S1 C7 90.73(17) . . ?
C5 N1 C1 122.8(3) . . ?
C5 N1 C16 121.5(3) . . ?
C1 N1 C16 115.8(3) . . ?
C3 N2 C7 114.3(3) . . ?
C3 N2 C8 125.3(3) . . ?
C7 N2 C8 120.4(3) . . ?
C7 N3 H3N 106(4) . . ?
O1 C1 N1 120.9(4) . . ?
O1 C1 C2 124.7(4) . . ?
N1 C1 C2 114.5(3) . . ?
C3 C2 C1 123.1(3) . . ?
C3 C2 S1 112.5(3) . . ?
C1 C2 S1 124.5(3) . . ?
N2 C3 C2 113.0(3) . . ?
N2 C3 C4 127.3(3) . . ?
C2 C3 C4 119.7(3) . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 N1 121.3(3) . . ?
C4 C5 C6 120.7(3) . . ?
N1 C5 C6 118.0(4) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 N2 121.4(4) . . ?
N3 C7 S1 129.1(4) . . ?
N2 C7 S1 109.5(3) . . ?
N2 C8 C9 113.4(3) . . ?
N2 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
N2 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C14 119.1(3) . . ?
C10 C9 C8 120.6(3) . . ?
C14 C9 C8 120.3(3) . . ?
C9 C10 C11 120.8(4) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 119.9(4) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 119.7(3) . . ?
C11 C12 C15 121.6(4) . . ?
C13 C12 C15 118.7(4) . . ?
C12 C13 C14 120.6(4) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C9 C14 C13 119.9(4) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
F1 C15 F2 106.7(3) . . ?
F1 C15 F3 106.4(3) . . ?
F2 C15 F3 106.4(4) . . ?
F1 C15 C12 113.0(4) . . ?
F2 C15 C12 111.3(3) . . ?
F3 C15 C12 112.7(3) . . ?
N1 C16 C17 114.1(3) . . ?
N1 C16 H16A 108.7 . . ?
C17 C16 H16A 108.7 . . ?
N1 C16 H16B 108.7 . . ?
C17 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C18 C17 C22 119.2(4) . . ?
C18 C17 C16 123.4(4) . . ?
C22 C17 C16 117.3(4) . . ?
C17 C18 C19 120.4(4) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 119.8(4) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.0(4) . . ?
C19 C20 C23 120.6(4) . . ?
C21 C20 C23 119.4(4) . . ?
C22 C21 C20 120.4(4) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C17 120.2(4) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?
F5 C23 F4 106.0(4) . . ?
F5 C23 F6 106.5(4) . . ?
F4 C23 F6 106.2(3) . . ?
F5 C23 C20 112.8(4) . . ?
F4 C23 C20 113.4(4) . . ?
F6 C23 C20 111.5(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
S1 C2 1.728(4) . ?
S1 C7 1.764(4) . ?
F1 C15 1.324(6) . ?
F2 C15 1.329(5) . ?
F3 C15 1.331(5) . ?
F4 C23 1.326(6) . ?
F5 C23 1.324(5) . ?
F6 C23 1.342(6) . ?
N1 C5 1.379(5) . ?
N1 C1 1.406(5) . ?
N1 C16 1.468(5) . ?
N2 C3 1.373(5) . ?
N2 C7 1.398(5) . ?
N2 C8 1.458(5) . ?
N3 C7 1.265(6) . ?
N3 H3N 0.848(7) . ?
O1 C1 1.239(5) . ?
C1 C2 1.412(6) . ?
C2 C3 1.373(5) . ?
C3 C4 1.410(5) . ?
C4 C5 1.355(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.500(6) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 C9 1.523(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.370(6) . ?
C9 C14 1.386(5) . ?
C10 C11 1.393(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.368(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(6) . ?
C12 C15 1.500(5) . ?
C13 C14 1.388(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C16 C17 1.514(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.376(5) . ?
C17 C22 1.390(6) . ?
C18 C19 1.385(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.375(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.375(6) . ?
C20 C23 1.498(6) . ?
C21 C22 1.369(6) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
