#------------------------------------------------------------------------------
#$Date: 2025-07-06 19:28:45 +0200 (Sun 06 de Jul de 2025) $
#$Revision: 301031 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/37/7063774.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_7063774
loop_
_publ_author_name
'Chávez-Vega, Tomás'
'Galdámez, Antonio'
'Lühr, Susan'
'Vilches-Herrera, Marcelo'
_publ_section_title
;
 Photocatalytic Heck--Matsuda reaction: selective arylation of N-vinyl-
 and N-allyl-lactams using Pd2(dba)3
;
_journal_issue                   22
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9416
_journal_page_last               9420
_journal_paper_doi               10.1039/D4NJ05413J
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         'C18 H12 F3 N O2'
_chemical_formula_sum            'C18 H12 F3 N O2'
_chemical_formula_weight         331.29
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2024-11-07
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-11-07 deposited with the CCDC.	2025-04-16 downloaded from the CCDC.
;
_cell_angle_alpha                106.032(15)
_cell_angle_beta                 95.710(15)
_cell_angle_gamma                91.249(16)
_cell_formula_units_Z            2
_cell_length_a                   5.053(2)
_cell_length_b                   10.600(5)
_cell_length_c                   14.685(6)
_cell_measurement_reflns_used    2619
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.860
_cell_measurement_theta_min      2.783
_cell_volume                     751.2(6)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0617
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20169
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_min         1.452
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.4992
_exptl_absorpt_correction_T_min  0.4175
_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            colorless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_description       papalelepided
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.097
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.027
_refine_diff_density_max         0.824
_refine_diff_density_min         -0.708
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2798
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1391
_refine_ls_R_factor_gt           0.0960
_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)+(0.1457P)²+1.1816P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2706
_refine_ls_wR_factor_ref         0.3154
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1728
_reflns_number_total             2798
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj05413j2.cif
_cod_data_source_block           scd24_161_0m
_cod_depositor_comments          'Adding full bibliography for 7063774.cif.'
_cod_original_cell_volume        751.2(5)
_cod_database_code               7063774
_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.
;
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.988
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15),
 C16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
F1 F -0.9524(15) 0.2477(7) -0.1434(5) 0.211(4) Uani 1 1 d . . . . .
F2 F -0.6224(15) 0.3104(16) -0.1661(7) 0.333(8) Uani 1 1 d . . . . .
F3 F -0.830(3) 0.4233(7) -0.0845(5) 0.299(8) Uani 1 1 d . . . . .
O1 O -0.2662(8) 0.0123(4) 0.4166(3) 0.0767(11) Uani 1 1 d . . . . .
O2 O 0.3864(7) 0.3041(4) 0.3967(3) 0.0689(10) Uani 1 1 d . . . . .
N1 N 0.0736(7) 0.1381(4) 0.3862(3) 0.0560(10) Uani 1 1 d . . . . .
C1 C -0.7522(15) 0.3127(7) -0.1014(5) 0.0867(19) Uani 1 1 d . . . . .
C2 C -0.6199(11) 0.2737(6) -0.0201(4) 0.0681(14) Uani 1 1 d . . . . .
C3 C -0.6794(13) 0.3276(6) 0.0709(5) 0.0848(18) Uani 1 1 d . . . . .
H3 H -0.809963 0.388890 0.082263 0.102 Uiso 1 1 calc R U . . .
C4 C -0.5460(11) 0.2915(6) 0.1467(4) 0.0739(15) Uani 1 1 d . . . . .
H4 H -0.586576 0.329660 0.208364 0.089 Uiso 1 1 calc R U . . .
C5 C -0.3543(9) 0.1997(5) 0.1312(3) 0.0574(12) Uani 1 1 d . . . . .
C6 C -0.3055(14) 0.1460(8) 0.0391(4) 0.099(2) Uani 1 1 d . . . . .
H6 H -0.175385 0.084685 0.026947 0.119 Uiso 1 1 calc R U . . .
C7 C -0.4410(15) 0.1788(8) -0.0371(4) 0.096(2) Uani 1 1 d . . . . .
H7 H -0.409731 0.136223 -0.099203 0.115 Uiso 1 1 calc R U . . .
C8 C -0.2099(9) 0.1682(5) 0.2138(3) 0.0561(12) Uani 1 1 d . . . . .
H8 H -0.255078 0.213158 0.273698 0.067 Uiso 1 1 calc R U . . .
C9 C -0.0242(10) 0.0831(5) 0.2114(3) 0.0618(13) Uani 1 1 d . . . . .
H9 H 0.019334 0.037713 0.151419 0.074 Uiso 1 1 calc R U . . .
C10 C 0.1247(10) 0.0514(5) 0.2946(3) 0.0629(13) Uani 1 1 d . . . . .
H10A H 0.076318 -0.038364 0.292727 0.076 Uiso 1 1 calc R U . . .
H10B H 0.313932 0.056769 0.288856 0.076 Uiso 1 1 calc R U . . .
C11 C -0.1190(9) 0.1100(5) 0.4400(4) 0.0566(12) Uani 1 1 d . . . . .
C12 C -0.1023(8) 0.2236(4) 0.5269(3) 0.0512(11) Uani 1 1 d . . . . .
C13 C -0.2488(10) 0.2482(5) 0.6041(4) 0.0626(13) Uani 1 1 d . . . . .
H13 H -0.381637 0.188550 0.608243 0.075 Uiso 1 1 calc R U . . .
C14 C -0.1897(11) 0.3653(6) 0.6752(4) 0.0696(14) Uani 1 1 d . . . . .
H14 H -0.284676 0.384814 0.728046 0.084 Uiso 1 1 calc R U . . .
C15 C 0.0076(11) 0.4531(6) 0.6687(4) 0.0691(14) Uani 1 1 d . . . . .
H15 H 0.045222 0.530065 0.717893 0.083 Uiso 1 1 calc R U . . .
C16 C 0.1519(10) 0.4296(5) 0.5905(4) 0.0611(12) Uani 1 1 d . . . . .
H16 H 0.282238 0.490038 0.585643 0.073 Uiso 1 1 calc R U . . .
C17 C 0.0931(8) 0.3126(4) 0.5202(3) 0.0507(11) Uani 1 1 d . . . . .
C18 C 0.2106(9) 0.2586(5) 0.4296(3) 0.0536(11) 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'
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 0.0060 '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
C11 N1 C10 123.6(4) . . ?
C11 N1 C18 112.4(4) . . ?
C18 N1 C10 124.0(4) . . ?
F1 C1 C2 116.8(5) . . ?
F2 C1 F1 101.4(9) . . ?
F2 C1 F3 101.2(9) . . ?
F2 C1 C2 116.7(7) . . ?
F3 C1 F1 101.6(9) . . ?
F3 C1 C2 116.7(7) . . ?
C3 C2 C1 121.7(6) . . ?
C7 C2 C1 118.7(6) . . ?
C7 C2 C3 119.6(5) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(6) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.7(5) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C8 118.9(5) . . ?
C6 C5 C4 117.0(5) . . ?
C6 C5 C8 124.0(5) . . ?
C5 C6 H6 118.5 . . ?
C5 C6 C7 122.9(6) . . ?
C7 C6 H6 118.5 . . ?
C2 C7 C6 119.2(6) . . ?
C2 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C5 C8 H8 116.7 . . ?
C9 C8 C5 126.5(5) . . ?
C9 C8 H8 116.7 . . ?
C8 C9 H9 116.5 . . ?
C8 C9 C10 126.9(5) . . ?
C10 C9 H9 116.5 . . ?
N1 C10 C9 113.6(4) . . ?
N1 C10 H10A 108.8 . . ?
N1 C10 H10B 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
O1 C11 N1 124.6(5) . . ?
O1 C11 C12 129.8(5) . . ?
N1 C11 C12 105.5(4) . . ?
C13 C12 C11 130.4(4) . . ?
C17 C12 C11 108.2(4) . . ?
C17 C12 C13 121.4(5) . . ?
C12 C13 H13 121.3 . . ?
C12 C13 C14 117.4(5) . . ?
C14 C13 H13 121.3 . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.0(5) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 119.1 . . ?
C14 C15 C16 121.7(5) . . ?
C16 C15 H15 119.1 . . ?
C15 C16 H16 121.5 . . ?
C17 C16 C15 117.0(5) . . ?
C17 C16 H16 121.5 . . ?
C12 C17 C16 121.4(4) . . ?
C12 C17 C18 108.4(4) . . ?
C16 C17 C18 130.2(4) . . ?
O2 C18 N1 124.6(4) . . ?
O2 C18 C17 129.9(4) . . ?
N1 C18 C17 105.5(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
F1 C1 1.221(7) . ?
F2 C1 1.203(9) . ?
F3 C1 1.212(9) . ?
O1 C11 1.210(6) . ?
O2 C18 1.205(5) . ?
N1 C10 1.455(6) . ?
N1 C11 1.390(6) . ?
N1 C18 1.393(6) . ?
C1 C2 1.473(8) . ?
C2 C3 1.367(8) . ?
C2 C7 1.356(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.378(7) . ?
C5 C6 1.365(8) . ?
C5 C8 1.475(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(9) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.312(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.491(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.486(7) . ?
C12 C13 1.383(7) . ?
C12 C17 1.380(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.388(8) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.389(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(7) . ?
C17 C18 1.483(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
F1 C1 C2 C3 -92.0(10) . . . . ?
F1 C1 C2 C7 85.8(10) . . . . ?
F2 C1 C2 C3 147.9(11) . . . . ?
F2 C1 C2 C7 -34.2(13) . . . . ?
F3 C1 C2 C3 28.3(12) . . . . ?
F3 C1 C2 C7 -153.9(10) . . . . ?
O1 C11 C12 C13 0.2(8) . . . . ?
O1 C11 C12 C17 -178.4(5) . . . . ?
N1 C11 C12 C13 179.3(4) . . . . ?
N1 C11 C12 C17 0.6(5) . . . . ?
C1 C2 C3 C4 -178.2(6) . . . . ?
C1 C2 C7 C6 176.7(7) . . . . ?
C2 C3 C4 C5 -0.8(9) . . . . ?
C3 C2 C7 C6 -5.4(10) . . . . ?
C3 C4 C5 C6 -0.7(9) . . . . ?
C3 C4 C5 C8 177.5(5) . . . . ?
C4 C5 C6 C7 -0.8(11) . . . . ?
C4 C5 C8 C9 179.5(5) . . . . ?
C5 C6 C7 C2 3.9(12) . . . . ?
C5 C8 C9 C10 179.4(5) . . . . ?
C6 C5 C8 C9 -2.4(9) . . . . ?
C7 C2 C3 C4 3.9(10) . . . . ?
C8 C5 C6 C7 -179.0(6) . . . . ?
C8 C9 C10 N1 -8.0(8) . . . . ?
C10 N1 C11 O1 -0.9(7) . . . . ?
C10 N1 C11 C12 179.9(4) . . . . ?
C10 N1 C18 O2 -0.3(7) . . . . ?
C10 N1 C18 C17 179.7(4) . . . . ?
C11 N1 C10 C9 93.8(6) . . . . ?
C11 N1 C18 O2 180.0(4) . . . . ?
C11 N1 C18 C17 -0.1(5) . . . . ?
C11 C12 C13 C14 -179.2(4) . . . . ?
C11 C12 C17 C16 179.2(4) . . . . ?
C11 C12 C17 C18 -0.7(5) . . . . ?
C12 C13 C14 C15 -0.1(7) . . . . ?
C12 C17 C18 O2 -179.6(5) . . . . ?
C12 C17 C18 N1 0.5(5) . . . . ?
C13 C12 C17 C16 0.4(7) . . . . ?
C13 C12 C17 C18 -179.5(4) . . . . ?
C13 C14 C15 C16 1.2(8) . . . . ?
C14 C15 C16 C17 -1.4(8) . . . . ?
C15 C16 C17 C12 0.7(7) . . . . ?
C15 C16 C17 C18 -179.5(5) . . . . ?
C16 C17 C18 O2 0.6(8) . . . . ?
C16 C17 C18 N1 -179.4(4) . . . . ?
C17 C12 C13 C14 -0.7(7) . . . . ?
C18 N1 C10 C9 -85.9(6) . . . . ?
C18 N1 C11 O1 178.8(4) . . . . ?
C18 N1 C11 C12 -0.3(5) . . . . ?
