#------------------------------------------------------------------------------
#$Date: 2022-10-15 03:43:28 +0300 (Sat, 15 Oct 2022) $
#$Revision: 278601 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/89/7158929.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_7158929
loop_
_publ_author_name
'Bannykh, Anton'
'Levashova, Ekaterina'
'Bakulina, Olga'
'Krasavin, Mikhail'
_publ_section_title
;
 New Reagent Space and New Scope for the Castagnoli-Cushman Reaction of
 Oximes and 3-Arylglutaconic anhydrides
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01675C
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H18 F N O2'
_chemical_formula_sum            'C16 H18 F N O2'
_chemical_formula_weight         275.31
_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_Hall           'P 31'
_space_group_name_H-M_alt        'P 31'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-04-11 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   9.9484(3)
_cell_length_b                   9.9484(3)
_cell_length_c                   11.8653(4)
_cell_measurement_reflns_used    6085
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      1.00000
_cell_measurement_theta_min      0.79156
_cell_volume                     1016.99(6)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10563
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.827
_diffrn_reflns_theta_min         5.134
_exptl_absorpt_coefficient_mu    0.805
_exptl_crystal_colour            'clear orangish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       prism
_exptl_crystal_F_000             438
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1110 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.17(12)
_refine_ls_extinction_coef       0.0031(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0324
_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)+(0.0380P)²+0.1469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0827
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_full    0.905
_reflns_Friedel_fraction_max     0.846
_reflns_number_gt                2536
_reflns_number_total             2685
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01675c2.cif
_cod_data_source_block           1ver1-20724_abb-761
_cod_original_cell_volume        1016.99(7)
_cod_database_code               7158929
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C12(H12), C13(H13), C15(H15), C16(H16)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
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
F001 F 0.52779(19) 0.76565(19) 0.11468(13) 0.0362(4) Uani 1 1 d . . . . .
O1 O 0.82472(19) 0.57237(19) 0.86010(13) 0.0244(4) Uani 1 1 d . . . . .
H1 H 0.749600 0.512931 0.901331 0.037 Uiso 1 1 calc R U . . .
O2 O 0.79213(19) 0.39200(19) 0.68599(14) 0.0258(4) Uani 1 1 d . . . . .
N1 N 0.7689(2) 0.5914(2) 0.75650(16) 0.0229(4) Uani 1 1 d . . . . .
C1 C 0.7642(3) 0.4994(3) 0.6722(2) 0.0220(5) Uani 1 1 d . . . . .
C2 C 0.7231(3) 0.5292(3) 0.5565(2) 0.0247(5) Uani 1 1 d . . . . .
H2A H 0.811770 0.554727 0.505802 0.030 Uiso 1 1 calc R U . . .
H2B H 0.633737 0.431460 0.528670 0.030 Uiso 1 1 calc R U . . .
C3 C 0.6831(2) 0.6551(3) 0.54599(19) 0.0217(5) Uani 1 1 d . . . . .
C4 C 0.6951(3) 0.7410(3) 0.6353(2) 0.0243(5) Uani 1 1 d . . . . .
H4 H 0.669070 0.819817 0.624158 0.029 Uiso 1 1 calc R U . . .
C5 C 0.7452(3) 0.7270(3) 0.7517(2) 0.0220(5) Uani 1 1 d . . . . .
C6 C 0.6173(3) 0.6992(3) 0.8368(2) 0.0264(5) Uani 1 1 d . . . . .
H6A H 0.518036 0.609425 0.811619 0.032 Uiso 1 1 calc R U . . .
H6B H 0.643614 0.672814 0.910968 0.032 Uiso 1 1 calc R U . . .
C7 C 0.5962(3) 0.8402(3) 0.8503(2) 0.0315(5) Uani 1 1 d . . . . .
H7A H 0.559058 0.860374 0.778283 0.038 Uiso 1 1 calc R U . . .
H7B H 0.516590 0.818257 0.908573 0.038 Uiso 1 1 calc R U . . .
C8 C 0.7476(4) 0.9830(3) 0.8839(3) 0.0367(6) Uani 1 1 d . . . . .
H8A H 0.779373 0.966624 0.959335 0.044 Uiso 1 1 calc R U . . .
H8B H 0.732020 1.073660 0.888362 0.044 Uiso 1 1 calc R U . . .
C9 C 0.8757(3) 1.0163(3) 0.7989(3) 0.0344(6) Uani 1 1 d . . . . .
H9A H 0.974367 1.105559 0.825594 0.041 Uiso 1 1 calc R U . . .
H9B H 0.849442 1.045064 0.725709 0.041 Uiso 1 1 calc R U . . .
C10 C 0.8977(3) 0.8763(3) 0.7823(2) 0.0270(5) Uani 1 1 d . . . . .
H10A H 0.940169 0.858162 0.852512 0.032 Uiso 1 1 calc R U . . .
H10B H 0.974556 0.899596 0.721577 0.032 Uiso 1 1 calc R U . . .
C11 C 0.6363(2) 0.6809(3) 0.4331(2) 0.0212(5) Uani 1 1 d . . . . .
C12 C 0.5993(3) 0.7977(3) 0.4145(2) 0.0256(5) Uani 1 1 d . . . . .
H12 H 0.600393 0.859043 0.476274 0.031 Uiso 1 1 calc R U . . .
C13 C 0.5611(3) 0.8257(3) 0.3087(2) 0.0282(5) Uani 1 1 d . . . . .
H13 H 0.536114 0.905148 0.297124 0.034 Uiso 1 1 calc R U . . .
C14 C 0.5603(3) 0.7351(3) 0.2195(2) 0.0252(5) Uani 1 1 d . . . . .
C15 C 0.5911(3) 0.6169(3) 0.2333(2) 0.0260(5) Uani 1 1 d . . . . .
H15 H 0.586833 0.554491 0.171262 0.031 Uiso 1 1 calc R U . . .
C16 C 0.6288(3) 0.5903(3) 0.3406(2) 0.0232(5) Uani 1 1 d . . . . .
H16 H 0.650079 0.508181 0.351457 0.028 Uiso 1 1 calc R U . . .
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'
F F 0.0727 0.0534 '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'
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 O1 H1 109.5 . . ?
O1 N1 C5 114.27(17) . . ?
C1 N1 O1 116.35(17) . . ?
C1 N1 C5 128.7(2) . . ?
O2 C1 N1 122.8(2) . . ?
O2 C1 C2 119.3(2) . . ?
N1 C1 C2 117.84(19) . . ?
C1 C2 H2A 108.1 . . ?
C1 C2 H2B 108.1 . . ?
H2A C2 H2B 107.3 . . ?
C3 C2 C1 116.93(19) . . ?
C3 C2 H2A 108.1 . . ?
C3 C2 H2B 108.1 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 C11 122.95(19) . . ?
C11 C3 C2 117.28(19) . . ?
C3 C4 H4 116.5 . . ?
C3 C4 C5 127.0(2) . . ?
C5 C4 H4 116.5 . . ?
N1 C5 C4 109.37(19) . . ?
N1 C5 C6 107.76(18) . . ?
N1 C5 C10 109.82(18) . . ?
C4 C5 C6 109.77(19) . . ?
C4 C5 C10 109.88(19) . . ?
C6 C5 C10 110.21(19) . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 C5 112.64(19) . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 C6 111.0(2) . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C7 C8 C9 111.1(2) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
C8 C9 C10 111.9(2) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C5 C10 H10A 109.0 . . ?
C5 C10 H10B 109.0 . . ?
C9 C10 C5 112.8(2) . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C3 121.4(2) . . ?
C16 C11 C3 121.2(2) . . ?
C16 C11 C12 117.4(2) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.5(2) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 H13 120.8 . . ?
C12 C13 C14 118.4(2) . . ?
C14 C13 H13 120.8 . . ?
F001 C14 C13 118.6(2) . . ?
F001 C14 C15 118.9(2) . . ?
C15 C14 C13 122.5(2) . . ?
C14 C15 H15 120.9 . . ?
C14 C15 C16 118.1(2) . . ?
C16 C15 H15 120.9 . . ?
C11 C16 H16 119.0 . . ?
C15 C16 C11 121.9(2) . . ?
C15 C16 H16 119.0 . . ?
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
F001 C14 1.357(3) . ?
O1 H1 0.8400 . ?
O1 N1 1.400(2) . ?
O2 C1 1.242(3) . ?
N1 C1 1.341(3) . ?
N1 C5 1.482(3) . ?
C1 C2 1.504(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.497(3) . ?
C3 C4 1.329(3) . ?
C3 C11 1.483(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.498(3) . ?
C5 C6 1.537(3) . ?
C5 C10 1.545(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.527(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.519(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.526(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.527(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.401(3) . ?
C11 C16 1.398(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(3) . ?
C14 C15 1.366(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(4) . ?
C16 H16 0.9500 . ?
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
F001 C14 C15 C16 178.0(2) . . . . ?
O1 N1 C1 O2 7.1(3) . . . . ?
O1 N1 C1 C2 -172.90(18) . . . . ?
O1 N1 C5 C4 176.54(17) . . . . ?
O1 N1 C5 C6 -64.2(2) . . . . ?
O1 N1 C5 C10 55.9(2) . . . . ?
O2 C1 C2 C3 177.1(2) . . . . ?
N1 C1 C2 C3 -2.9(3) . . . . ?
N1 C5 C6 C7 172.9(2) . . . . ?
N1 C5 C10 C9 -170.2(2) . . . . ?
C1 N1 C5 C4 6.4(3) . . . . ?
C1 N1 C5 C6 125.6(2) . . . . ?
C1 N1 C5 C10 -114.3(2) . . . . ?
C1 C2 C3 C4 4.4(3) . . . . ?
C1 C2 C3 C11 -177.59(19) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C2 C3 C11 C12 -178.9(2) . . . . ?
C2 C3 C11 C16 0.5(3) . . . . ?
C3 C4 C5 N1 -4.5(3) . . . . ?
C3 C4 C5 C6 -122.6(2) . . . . ?
C3 C4 C5 C10 116.1(2) . . . . ?
C3 C11 C12 C13 177.6(2) . . . . ?
C3 C11 C16 C15 -177.4(2) . . . . ?
C4 C3 C11 C12 -1.0(3) . . . . ?
C4 C3 C11 C16 178.4(2) . . . . ?
C4 C5 C6 C7 -68.1(3) . . . . ?
C4 C5 C10 C9 69.5(3) . . . . ?
C5 N1 C1 O2 177.1(2) . . . . ?
C5 N1 C1 C2 -2.9(3) . . . . ?
C5 C6 C7 C8 -56.2(3) . . . . ?
C6 C5 C10 C9 -51.6(3) . . . . ?
C6 C7 C8 C9 56.3(3) . . . . ?
C7 C8 C9 C10 -55.2(3) . . . . ?
C8 C9 C10 C5 53.4(3) . . . . ?
C10 C5 C6 C7 53.1(3) . . . . ?
C11 C3 C4 C5 -178.3(2) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C12 C11 C16 C15 2.0(3) . . . . ?
C12 C13 C14 F001 -177.9(2) . . . . ?
C12 C13 C14 C15 2.0(4) . . . . ?
C13 C14 C15 C16 -1.8(4) . . . . ?
C14 C15 C16 C11 -0.2(3) . . . . ?
C16 C11 C12 C13 -1.8(3) . . . . ?
